#------------------------------------------------------------------------------ #$Date: 2026-03-04 22:02:50 +0000 (Wed, 04 Mar 2026) $ #$Revision: 304785 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064321.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7064321 loop_ _publ_author_name 'Moskalik, Mikhail Yu.' 'Garagan, Ivan A.' 'Myasnikova, Valentina S.' 'Borodina, Tatyana N.' 'Shainyan, Bagrat A.' _publ_section_title ; Skeletal rearrangements and structures of halosulfonamidation products of caryophyllene ; _journal_issue 4 _journal_name_full 'New Journal of Chemistry' _journal_page_first 1935 _journal_page_last 1942 _journal_paper_doi 10.1039/D5NJ03976B _journal_volume 50 _journal_year 2026 _chemical_formula_moiety 'C24 H32 Br F3 N2 O2 S' _chemical_formula_sum 'C24 H32 Br F3 N2 O2 S' _chemical_formula_weight 549.48 _chemical_melting_point 480.3 _chemical_name_systematic N-(6-bromo-1,1,7-trimethyldecahydro-3a,7-methanocyclopenta[8]annulen-3-yl)-N'-((4-(trifluoromethyl)phenyl)sulfonyl)acetimidamide _space_group_crystal_system triclinic _space_group_IT_number 1 _space_group_name_Hall 'P 1' _space_group_name_H-M_alt 'P 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2025-02-25 _audit_creation_method ; Olex2 1.5 (compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928) ; _audit_update_record ; 2025-03-13 deposited with the CCDC. 2025-12-17 downloaded from the CCDC. ; _cell_angle_alpha 90.113(4) _cell_angle_beta 93.196(4) _cell_angle_gamma 93.055(4) _cell_formula_units_Z 2 _cell_length_a 10.3167(13) _cell_length_b 10.7257(14) _cell_length_c 11.5944(14) _cell_measurement_reflns_used 9916 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 29.25 _cell_measurement_theta_min 2.57 _cell_volume 1279.1(3) _computing_cell_refinement 'SAINT V8.32B (BRUKER, 2016)' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'SAINT V8.32B (BRUKER, 2016)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _diffrn_ambient_temperature 296.15 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker D8 VENTURE PHOTON 100 CMOS' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0778 _diffrn_reflns_av_unetI/netI 0.0847 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 61939 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.985 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.760 _diffrn_reflns_theta_min 2.574 _diffrn_source_current 1.0 _diffrn_source_power 0.05 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.733 _exptl_absorpt_correction_T_max 0.7459 _exptl_absorpt_correction_T_min 0.2883 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1427 before and 0.0984 after correction. The Ratio of minimum to maximum transmission is 0.3865. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.427 _exptl_crystal_description prism _exptl_crystal_F_000 568 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: chloroform' _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.595 _exptl_crystal_size_min 0.595 _refine_diff_density_max 0.693 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.070 _refine_ls_abs_structure_details ; Flack x determined using 3735 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.094(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 603 _refine_ls_number_reflns 14380 _refine_ls_number_restraints 399 _refine_ls_restrained_S_all 1.114 _refine_ls_R_factor_all 0.0961 _refine_ls_R_factor_gt 0.0555 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0797P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1371 _refine_ls_wR_factor_ref 0.1505 _reflns_Friedel_coverage 0.984 _reflns_Friedel_fraction_full 0.989 _reflns_Friedel_fraction_max 0.977 _reflns_number_gt 9899 _reflns_number_total 14380 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5nj03976b2.cif _cod_data_source_block 3h _cod_database_code 7064321 _shelxl_version_number 2013-3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.425 _shelx_estimated_absorpt_t_min 0.423 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2. Uiso/Uaniso restraints and constraints Uanis(F2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(F1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(F3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(F102) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(F101) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(F103) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(F3) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F101) \\sim Ueq, Uanis(F102) \\sim Ueq, Uanis(F103) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1 Uanis(C122) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1 Uanis(C119) \\sim Ueq, Uanis(Br1A) \\sim Ueq, Uanis(C106) \\sim Ueq, Uanis(C107) \\sim Ueq, Uanis(C105) \\sim Ueq, Uanis(C110) \\sim Ueq, Uanis(C108) \\sim Ueq, Uanis(C113) \\sim Ueq, Uanis(C104) \\sim Ueq, Uanis(C13A) \\sim Ueq, Uanis(C109) \\sim Ueq, Uanis(C103) \\sim Ueq, Uanis(C19A) \\sim Ueq, Uanis(N101) \\sim Ueq, Uanis(C102) \\sim Ueq, Uanis(C101) \\sim Ueq, Uanis(C114) \\sim Ueq, Uanis(C112) \\sim Ueq, Uanis(C111) \\sim Ueq, Uanis(N102) \\sim Ueq, Uanis(C115) \\sim Ueq, Uanis(S101) \\sim Ueq, Uanis(O102) \\sim Ueq, Uanis(O101) \\sim Ueq, Uanis(C116) \\sim Ueq, Uanis(C121) \\sim Ueq, Uanis(C117) \\sim Ueq, Uanis(C120) \\sim Ueq, Uanis(C118) \\sim Ueq, Uanis(C122) \\sim Ueq, Uanis(F101) \\sim Ueq, Uanis(F103) \\sim Ueq, Uanis(F102) \\sim Ueq, Uanis(Br1) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C9A) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(S1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1 Uanis(F103) \\sim Ueq, Uanis(F102) \\sim Ueq, Uanis(F101) \\sim Ueq, Uanis(C122) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1 Uanis(C122) \\sim Ueq, Uanis(F102) \\sim Ueq, Uanis(F101) \\sim Ueq, Uanis(F103) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01 3.a Ternary CH refined with riding coordinates: C3(H3), C6(H6), C9A(H9A), C103(H103), C106(H106), C19A(H19A) 3.b Secondary CH2 refined with riding coordinates: C10(H10A,H10B), C8(H8A,H8B), C5(H5A,H5B), C4(H4A,H4B), C2(H2A,H2B), C9(H9B, H9C), C110(H11G,H11H), C105(H10C,H10D), C104(H10E,H10F), C108(H10G,H10H), C109(H10I,H10J), C102(H10K,H10L) 3.c Aromatic/amide H refined with riding coordinates: C18(H18), C20(H20), C21(H21), N1(H1), C17(H17), N101(H101), C121(H121), C120(H120), C117(H117), C118(H118) 3.d Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C11(H11A,H11B,H11C), C12(H12A,H12B, H12C), C113(H11D,H11E,H11F), C115(H11I,H11J,H11K), C112(H11L,H11M,H11N), C111(H11O,H11P,H11Q) ; _shelx_res_file ; TITL 01 in P1 CELL 0.71073 10.3167 10.7257 11.5944 90.113 93.196 93.055 ZERR 2 0.0013 0.0014 0.0014 0.004 0.004 0.004 LATT -1 SFAC C H N O F S Br UNIT 48 64 4 4 6 2 2 ISOR 0.01 0.02 F2 ISOR 0.01 0.02 F1 ISOR 0.01 0.02 F3 ISOR 0.01 0.02 F102 ISOR 0.01 0.02 F101 ISOR 0.01 0.02 F103 ISOR 0.05 0.1 F3 F2 F1 F101 F102 F103 ISOR 0.05 0.1 C122 ISOR 0.05 0.1 C119 Br1A C106 C107 H106 C105 C110 C108 C113 H10c H10d C104 = H11G H11H C13A H10G H10H C109 H11D H11E H11F H10E H10F C103 C19A H10I H10J = H103 N101 C102 H19A C101 H101 C114 H10K H10L C112 C111 N102 C115 H11L H11M = H11N H11O H11P H11Q S101 H11I H11J H11K O102 O101 C116 C121 C117 H121 C120 = H117 C118 H120 H118 C122 F101 F103 F102 BR1 C6 C7 H6 C5 C13 C10 C8 H5A H5B = C4 H13A H13B H13C C3A H10A H10B H8A H8B C9 H4A H4B C3 C9A H9B H9C N1 H3 C2 = H9A C14 H1 H2A H2B C11 C12 N2 C15 H11A H11B H11C H12A H12B H12C S1 H15A = H15B H15C O2 O1 C16 C21 C17 C20 H21 H17 C18 H20 C19 H18 C22 F3 F1 F2 C1 ISOR 0.05 0.1 F103 F102 F101 C122 ISOR 0.005 0.01 C122 F102 F101 F103 L.S. 25 PLAN 13 SIZE 0.595 0.595 0.6 TEMP -273.15 CONF BOND $H MORE -1 HTAB fmap 2 acta REM REM REM WGHT 0.079700 FVAR 0.17978 BR1 7 0.013735 0.239930 0.231487 11.00000 0.04511 0.11098 = 0.12554 -0.01477 0.00143 0.01585 BR1A 7 0.985177 0.759890 0.777214 11.00000 0.04871 0.12736 = 0.14823 0.02320 0.00701 0.02356 C22 1 -0.195750 0.585861 0.159589 11.00000 0.05454 0.09186 = 0.13646 0.02694 0.02691 0.00969 S1 6 0.383561 0.659638 0.147852 11.00000 0.04808 0.02151 = 0.03770 0.00089 0.01292 0.00496 S101 6 0.606987 0.336993 0.654498 11.00000 0.04829 0.02100 = 0.03289 -0.00031 0.00011 0.00404 F3 5 -0.257889 0.650378 0.087799 11.00000 0.06465 0.21286 = 0.35392 0.12840 -0.02588 0.01735 C13 1 0.097143 0.164847 -0.024302 11.00000 0.07037 0.06969 = 0.09233 0.00180 -0.04096 -0.00511 AFIX 137 H13A 2 0.070874 0.249738 -0.010072 11.00000 -1.50000 H13B 2 0.019901 0.107444 -0.030498 11.00000 -1.50000 H13C 2 0.142201 0.163014 -0.096445 11.00000 -1.50000 AFIX 0 F1 5 -0.238288 0.479326 0.136808 11.00000 0.08206 0.10136 = 0.48900 0.00565 0.02725 -0.03614 F2 5 -0.240676 0.607760 0.248630 11.00000 0.05189 0.59403 = 0.21893 -0.08961 0.03244 -0.05613 O2 4 0.422106 0.757100 0.229099 11.00000 0.06321 0.02298 = 0.05793 -0.00523 0.00959 0.00019 O1 4 0.412966 0.682101 0.029831 11.00000 0.07948 0.04214 = 0.05117 0.01351 0.02701 0.01649 O102 4 0.591851 0.242647 0.740846 11.00000 0.07614 0.02344 = 0.04696 0.00452 0.00973 0.00177 O101 4 0.552942 0.306083 0.540850 11.00000 0.06344 0.03538 = 0.04544 -0.00714 -0.01080 0.00722 C18 1 0.015913 0.663464 0.241967 11.00000 0.05780 0.10207 = 0.07721 -0.01044 0.02482 0.01699 AFIX 43 H18 2 -0.027916 0.692977 0.305711 11.00000 -1.20000 AFIX 0 C19 1 -0.052497 0.605402 0.156149 11.00000 0.04745 0.06573 = 0.08525 0.01376 -0.00091 0.01386 C20 1 0.012652 0.560793 0.062000 11.00000 0.06607 0.10459 = 0.08787 -0.02492 -0.02878 0.00541 AFIX 43 H20 2 -0.035937 0.518675 0.000250 11.00000 -1.20000 AFIX 0 C21 1 0.144248 0.577119 0.058135 11.00000 0.06862 0.08511 = 0.05801 -0.02356 -0.00068 0.00625 AFIX 43 H21 2 0.187874 0.546532 -0.005280 11.00000 -1.20000 AFIX 0 C16 1 0.212695 0.639259 0.148721 11.00000 0.04955 0.02562 = 0.04249 0.00509 0.00594 0.00659 N2 3 0.433381 0.524769 0.179928 11.00000 0.04240 0.02179 = 0.03613 -0.00414 0.00835 0.00448 C14 1 0.461064 0.489953 0.285937 11.00000 0.03096 0.02433 = 0.03524 -0.00719 0.00499 -0.00205 N1 3 0.495001 0.374513 0.303897 11.00000 0.03962 0.02413 = 0.02952 -0.00497 0.00074 0.00203 AFIX 43 H1 2 0.510677 0.352100 0.376089 11.00000 -1.20000 AFIX 0 C3 1 0.508929 0.280484 0.214825 11.00000 0.03646 0.01995 = 0.02948 -0.00363 0.00228 0.00239 AFIX 13 H3 2 0.524991 0.323901 0.140313 11.00000 -1.20000 AFIX 0 C3A 1 0.392504 0.185503 0.194962 11.00000 0.04156 0.01921 = 0.03628 -0.00082 -0.00094 0.00102 C10 1 0.294706 0.227722 0.101374 11.00000 0.04769 0.02932 = 0.04210 0.00306 -0.00898 0.00043 AFIX 23 H10A 2 0.339881 0.247714 0.030049 11.00000 -1.20000 H10B 2 0.254893 0.304179 0.127281 11.00000 -1.20000 AFIX 0 C7 1 0.188614 0.124702 0.076020 11.00000 0.05305 0.03783 = 0.05976 0.00201 -0.01699 -0.00847 C8 1 0.251601 0.000490 0.040371 11.00000 0.07497 0.03831 = 0.06385 -0.01176 -0.02250 -0.00831 AFIX 23 H8A 2 0.225892 -0.066702 0.094267 11.00000 -1.20000 H8B 2 0.216937 -0.024586 -0.038080 11.00000 -1.20000 AFIX 0 C6 1 0.116583 0.098063 0.186050 11.00000 0.04491 0.05520 = 0.07403 -0.00213 -0.00776 -0.01379 AFIX 13 H6 2 0.054887 0.024059 0.170633 11.00000 -1.20000 AFIX 0 C5 1 0.208291 0.067229 0.290067 11.00000 0.04941 0.05490 = 0.06165 0.01183 0.00497 -0.00975 AFIX 23 H5A 2 0.158886 0.064135 0.360887 11.00000 -1.20000 H5B 2 0.242387 -0.016160 0.278475 11.00000 -1.20000 AFIX 0 C4 1 0.321181 0.163475 0.305933 11.00000 0.04021 0.03697 = 0.03989 0.00124 0.00221 0.00044 AFIX 23 H4A 2 0.383294 0.135026 0.367252 11.00000 -1.20000 H4B 2 0.288199 0.243349 0.331664 11.00000 -1.20000 AFIX 0 C17 1 0.149865 0.682446 0.241454 11.00000 0.05490 0.07887 = 0.05407 -0.01940 0.01080 0.00280 AFIX 43 H17 2 0.197425 0.724429 0.303851 11.00000 -1.20000 AFIX 0 C15 1 0.461477 0.567733 0.393483 11.00000 0.08974 0.02785 = 0.03968 -0.01016 0.00362 0.01172 AFIX 137 H15A 2 0.528454 0.635794 0.390595 11.00000 -1.50000 H15B 2 0.480047 0.515569 0.461080 11.00000 -1.50000 H15C 2 0.376198 0.602699 0.399104 11.00000 -1.50000 AFIX 0 C2 1 0.623513 0.200642 0.246289 11.00000 0.03500 0.02630 = 0.04349 -0.00263 -0.00116 0.00326 AFIX 23 H2A 2 0.620219 0.169853 0.326567 11.00000 -1.20000 H2B 2 0.707237 0.248347 0.237810 11.00000 -1.20000 AFIX 0 C1 1 0.605856 0.092549 0.159403 11.00000 0.04419 0.02338 = 0.04364 -0.00060 0.00655 0.01093 C9A 1 0.457925 0.064353 0.155343 11.00000 0.05076 0.01882 = 0.03810 0.00067 -0.00444 0.00502 AFIX 13 H9A 2 0.441054 -0.000675 0.215148 11.00000 -1.20000 AFIX 0 C9 1 0.395564 0.013137 0.041298 11.00000 0.06782 0.02972 = 0.05340 -0.01448 -0.00501 0.00489 AFIX 23 H9B 2 0.421177 0.069462 -0.022019 11.00000 -1.20000 H9C 2 0.429360 -0.069671 0.026233 11.00000 -1.20000 AFIX 0 C11 1 0.679505 -0.020240 0.201141 11.00000 0.05443 0.03850 = 0.07284 -0.00112 -0.00267 0.02234 AFIX 137 H11A 2 0.649639 -0.046852 0.276448 11.00000 -1.50000 H11B 2 0.772863 0.002582 0.208415 11.00000 -1.50000 H11C 2 0.663256 -0.088797 0.145331 11.00000 -1.50000 AFIX 0 C12 1 0.656854 0.134669 0.042579 11.00000 0.07012 0.04021 = 0.05152 -0.00411 0.01983 0.01183 AFIX 137 H12A 2 0.647784 0.064543 -0.012100 11.00000 -1.50000 H12B 2 0.748699 0.162761 0.053330 11.00000 -1.50000 H12C 2 0.606529 0.203502 0.012171 11.00000 -1.50000 AFIX 0 C113 1 0.898391 0.828923 0.514370 11.00000 0.07396 0.07159 = 0.09389 -0.01101 0.05066 -0.00501 AFIX 137 H11D 2 0.923342 0.743589 0.530751 11.00000 -1.50000 H11E 2 0.976417 0.885322 0.516366 11.00000 -1.50000 H11F 2 0.853636 0.831522 0.437674 11.00000 -1.50000 AFIX 0 C107 1 0.807461 0.870055 0.605451 11.00000 0.05549 0.04537 = 0.07139 -0.00530 0.03157 -0.00442 C110 1 0.700902 0.767678 0.621269 11.00000 0.05060 0.02720 = 0.04858 -0.00706 0.01699 -0.00025 AFIX 23 H11G 2 0.740661 0.691583 0.651770 11.00000 -1.20000 H11H 2 0.655994 0.746626 0.545499 11.00000 -1.20000 AFIX 0 C13A 1 0.602021 0.810318 0.704669 11.00000 0.03964 0.02248 = 0.03486 -0.00294 0.00613 0.00515 C103 1 0.485931 0.716750 0.715238 11.00000 0.03856 0.02021 = 0.03045 0.00067 0.00496 0.00371 AFIX 13 H103 2 0.467994 0.673361 0.639154 11.00000 -1.20000 AFIX 0 N101 3 0.498913 0.622570 0.804410 11.00000 0.04534 0.02454 = 0.02885 0.00035 0.00599 0.00018 AFIX 43 H101 2 0.485078 0.645295 0.875459 11.00000 -1.20000 AFIX 0 C114 1 0.529486 0.506282 0.788737 11.00000 0.03648 0.02609 = 0.03387 0.00239 0.00534 0.00113 N102 3 0.560593 0.471624 0.685305 11.00000 0.04836 0.02092 = 0.03341 0.00164 0.00579 0.00199 C116 1 0.775341 0.364774 0.642204 11.00000 0.04789 0.03020 = 0.04307 -0.00451 0.00035 0.00761 C121 1 0.856491 0.347280 0.734366 11.00000 0.05708 0.11901 = 0.07262 0.02431 -0.00613 0.01121 AFIX 43 H121 2 0.822888 0.321483 0.805652 11.00000 -1.20000 AFIX 0 C120 1 0.990055 0.366921 0.725616 11.00000 0.05965 0.14335 = 0.11756 0.01805 -0.01294 0.02240 AFIX 43 H120 2 1.047431 0.353424 0.790818 11.00000 -1.20000 AFIX 0 C119 1 1.038809 0.405259 0.624429 11.00000 0.04831 0.06209 = 0.12939 -0.01872 0.01214 0.00059 C106 1 0.879313 0.898440 0.722555 11.00000 0.04493 0.05777 = 0.09944 0.00053 0.01837 -0.00747 AFIX 13 H106 2 0.939714 0.973226 0.712644 11.00000 -1.20000 AFIX 0 C105 1 0.788624 0.929119 0.816616 11.00000 0.04989 0.05995 = 0.06495 -0.01512 0.00196 -0.00875 AFIX 23 H10C 2 0.838633 0.933216 0.892046 11.00000 -1.20000 H10D 2 0.754460 1.012379 0.801394 11.00000 -1.20000 AFIX 0 C104 1 0.675833 0.834051 0.823476 11.00000 0.04275 0.04628 = 0.04036 -0.00783 0.00242 -0.00245 AFIX 23 H10E 2 0.614698 0.863854 0.878983 11.00000 -1.20000 H10F 2 0.708690 0.754428 0.852947 11.00000 -1.20000 AFIX 0 C108 1 0.745185 0.992696 0.564954 11.00000 0.07701 0.04265 = 0.07099 0.00662 0.03473 -0.00744 AFIX 23 H10G 2 0.770446 1.059456 0.622198 11.00000 -1.20000 H10H 2 0.780569 1.018408 0.490488 11.00000 -1.20000 AFIX 0 C109 1 0.598839 0.980471 0.550116 11.00000 0.08051 0.03386 = 0.05663 0.01348 0.02069 0.00520 AFIX 23 H10I 2 0.572946 0.922589 0.485273 11.00000 -1.20000 H10J 2 0.565031 1.062970 0.530727 11.00000 -1.20000 AFIX 0 C19A 1 0.539210 0.931560 0.660080 11.00000 0.05098 0.01834 = 0.03994 -0.00435 0.01096 0.00162 AFIX 13 H19A 2 0.558408 0.996993 0.721105 11.00000 -1.20000 AFIX 0 C101 1 0.390197 0.904387 0.651643 11.00000 0.04998 0.02544 = 0.04583 -0.00274 -0.00176 0.00969 C102 1 0.371919 0.798147 0.736681 11.00000 0.03618 0.02870 = 0.04530 -0.00075 0.00479 0.00605 AFIX 23 H10K 2 0.287555 0.751235 0.720669 11.00000 -1.20000 H10L 2 0.376554 0.829549 0.817235 11.00000 -1.20000 AFIX 0 C115 1 0.524563 0.427400 0.894763 11.00000 0.09356 0.03428 = 0.03405 0.00666 0.01494 0.01255 AFIX 137 H11I 2 0.464101 0.354872 0.879680 11.00000 -1.50000 H11J 2 0.494874 0.476632 0.958541 11.00000 -1.50000 H11K 2 0.611488 0.399000 0.915555 11.00000 -1.50000 AFIX 0 C117 1 0.823282 0.403920 0.540324 11.00000 0.05693 0.14740 = 0.05789 0.01113 0.00805 -0.01468 AFIX 43 H117 2 0.765518 0.417107 0.475321 11.00000 -1.20000 AFIX 0 C118 1 0.954676 0.424256 0.531606 11.00000 0.08295 0.16316 = 0.09218 0.00248 0.04062 -0.02157 AFIX 43 H118 2 0.987513 0.451757 0.460521 11.00000 -1.20000 AFIX 0 C112 1 0.318088 1.019037 0.685975 11.00000 0.05871 0.03548 = 0.07621 -0.00621 -0.00295 0.01888 AFIX 137 H11L 2 0.344972 1.043129 0.765672 11.00000 -1.50000 H11M 2 0.224179 0.998849 0.680055 11.00000 -1.50000 H11N 2 0.339042 1.088385 0.634131 11.00000 -1.50000 AFIX 0 C111 1 0.334880 0.862554 0.530189 11.00000 0.07521 0.04850 = 0.05710 -0.00074 -0.01584 0.01153 AFIX 137 H11O 2 0.348335 0.930827 0.475365 11.00000 -1.50000 H11P 2 0.241643 0.840719 0.532864 11.00000 -1.50000 H11Q 2 0.379599 0.789601 0.505358 11.00000 -1.50000 AFIX 0 C122 1 1.178436 0.422416 0.613096 11.00000 0.09802 0.12324 = 0.14854 -0.02406 0.01760 0.00193 F101 5 1.217506 0.531979 0.589310 11.00000 0.11170 0.16663 = 0.31227 -0.00820 0.07047 -0.03350 F103 5 1.233261 0.348233 0.555873 11.00000 0.08681 0.23076 = 0.34955 -0.11812 0.06395 0.01014 F102 5 1.239787 0.431611 0.710623 11.00000 0.09258 0.42818 = 0.25247 0.02609 -0.00362 -0.04607 HKLF 4 REM 01 in P1 REM R1 = 0.0555 for 9899 Fo > 4sig(Fo) and 0.0961 for all 14380 data REM 603 parameters refined using 399 restraints END WGHT 0.0877 0.0000 REM Instructions for potential hydrogen bonds HTAB N1 O101 HTAB C15 O101 EQIV $1 x, y, z+1 HTAB N101 O1_$1 HTAB C115 O1_$1 REM Highest difference peak 0.693, deepest hole -0.442, 1-sigma level 0.070 Q1 1 1.2424 0.3235 0.6896 11.00000 0.05 0.69 Q2 1 1.2004 0.4591 0.4974 11.00000 0.05 0.67 Q3 1 1.2131 0.4929 0.7392 11.00000 0.05 0.41 Q4 1 -0.2366 0.5311 0.0568 11.00000 0.05 0.41 Q5 1 -0.2067 0.5140 0.2722 11.00000 0.05 0.41 Q6 1 -0.0105 0.2261 0.3089 11.00000 0.05 0.38 Q7 1 -0.2471 0.6835 0.1962 11.00000 0.05 0.38 Q8 1 -0.2388 0.6760 0.2723 11.00000 0.05 0.35 Q9 1 1.0092 0.7480 0.8432 11.00000 0.05 0.34 Q10 1 0.9684 0.3382 0.5454 11.00000 0.05 0.32 Q11 1 -0.2383 0.6851 0.3332 11.00000 0.05 0.31 Q12 1 1.1768 0.5813 0.5209 11.00000 0.05 0.28 Q13 1 0.3903 0.6656 0.0006 11.00000 0.05 0.28 ; _shelx_res_checksum 8709 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.01374(7) 0.23993(8) 0.23149(8) 0.0936(3) Uani 1 1 d . U . . . Br1A Br 0.98518(8) 0.75989(10) 0.77721(10) 0.1073(3) Uani 1 1 d . U . . . C22 C -0.1957(8) 0.5859(9) 0.1596(10) 0.093(3) Uani 1 1 d . U . . . S1 S 0.38356(10) 0.65964(9) 0.14785(9) 0.0353(2) Uani 1 1 d . U . . . S101 S 0.60699(10) 0.33699(9) 0.65450(8) 0.0341(2) Uani 1 1 d . U . . . F3 F -0.2579(6) 0.6504(10) 0.0878(12) 0.211(5) Uani 1 1 d . U . . . C13 C 0.0971(7) 0.1648(7) -0.0243(7) 0.079(2) Uani 1 1 d . U . . . H13A H 0.0709 0.2497 -0.0101 0.119 Uiso 1 1 calc R U . . . H13B H 0.0199 0.1074 -0.0305 0.119 Uiso 1 1 calc R U . . . H13C H 0.1422 0.1630 -0.0964 0.119 Uiso 1 1 calc R U . . . F1 F -0.2383(7) 0.4793(7) 0.1368(14) 0.225(5) Uani 1 1 d . U . . . F2 F -0.2407(7) 0.6078(19) 0.2486(11) 0.290(8) Uani 1 1 d . U . . . O2 O 0.4221(4) 0.7571(3) 0.2291(3) 0.0479(8) Uani 1 1 d . U . . . O1 O 0.4130(4) 0.6821(3) 0.0298(3) 0.0562(9) Uani 1 1 d . U . . . O102 O 0.5919(4) 0.2426(3) 0.7408(3) 0.0486(8) Uani 1 1 d . U . . . O101 O 0.5529(4) 0.3061(3) 0.5408(3) 0.0484(8) Uani 1 1 d . U . . . C18 C 0.0159(7) 0.6635(8) 0.2420(6) 0.0778(19) Uani 1 1 d . U . . . H18 H -0.0279 0.6930 0.3057 0.093 Uiso 1 1 calc R U . . . C19 C -0.0525(6) 0.6054(6) 0.1561(6) 0.0659(16) Uani 1 1 d . U . . . C20 C 0.0127(8) 0.5608(8) 0.0620(7) 0.087(2) Uani 1 1 d . U . . . H20 H -0.0359 0.5187 0.0003 0.105 Uiso 1 1 calc R U . . . C21 C 0.1442(7) 0.5771(7) 0.0581(5) 0.0707(17) Uani 1 1 d . U . . . H21 H 0.1879 0.5465 -0.0053 0.085 Uiso 1 1 calc R U . . . C16 C 0.2127(5) 0.6393(4) 0.1487(4) 0.0389(9) Uani 1 1 d . U . . . N2 N 0.4334(4) 0.5248(3) 0.1799(3) 0.0331(7) Uani 1 1 d . U . . . C14 C 0.4611(4) 0.4900(3) 0.2859(3) 0.0302(8) Uani 1 1 d . U . . . N1 N 0.4950(3) 0.3745(3) 0.3039(3) 0.0311(7) Uani 1 1 d . U . . . H1 H 0.5107 0.3521 0.3761 0.037 Uiso 1 1 calc R U . . . C3 C 0.5089(4) 0.2805(3) 0.2148(3) 0.0286(7) Uani 1 1 d . U . . . H3 H 0.5250 0.3239 0.1403 0.034 Uiso 1 1 calc R U . . . C3A C 0.3925(4) 0.1855(3) 0.1950(3) 0.0325(8) Uani 1 1 d . U . . . C10 C 0.2947(5) 0.2277(4) 0.1014(4) 0.0402(10) Uani 1 1 d . U . . . H10A H 0.3399 0.2477 0.0300 0.048 Uiso 1 1 calc R U . . . H10B H 0.2549 0.3042 0.1273 0.048 Uiso 1 1 calc R U . . . C7 C 0.1886(5) 0.1247(5) 0.0760(5) 0.0514(12) Uani 1 1 d . U . . . C8 C 0.2516(6) 0.0005(5) 0.0404(5) 0.0605(15) Uani 1 1 d . U . . . H8A H 0.2259 -0.0667 0.0943 0.073 Uiso 1 1 calc R U . . . H8B H 0.2169 -0.0246 -0.0381 0.073 Uiso 1 1 calc R U . . . C6 C 0.1166(6) 0.0981(5) 0.1860(5) 0.0591(14) Uani 1 1 d . U . . . H6 H 0.0549 0.0241 0.1706 0.071 Uiso 1 1 calc R U . . . C5 C 0.2083(6) 0.0672(5) 0.2901(5) 0.0557(13) Uani 1 1 d . U . . . H5A H 0.1589 0.0641 0.3609 0.067 Uiso 1 1 calc R U . . . H5B H 0.2424 -0.0162 0.2785 0.067 Uiso 1 1 calc R U . . . C4 C 0.3212(5) 0.1635(4) 0.3059(4) 0.0391(9) Uani 1 1 d . U . . . H4A H 0.3833 0.1350 0.3673 0.047 Uiso 1 1 calc R U . . . H4B H 0.2882 0.2433 0.3317 0.047 Uiso 1 1 calc R U . . . C17 C 0.1499(6) 0.6824(6) 0.2415(5) 0.0624(15) Uani 1 1 d . U . . . H17 H 0.1974 0.7244 0.3039 0.075 Uiso 1 1 calc R U . . . C15 C 0.4615(6) 0.5677(4) 0.3935(4) 0.0521(13) Uani 1 1 d . U . . . H15A H 0.5285 0.6358 0.3906 0.078 Uiso 1 1 calc R U . . . H15B H 0.4800 0.5156 0.4611 0.078 Uiso 1 1 calc R U . . . H15C H 0.3762 0.6027 0.3991 0.078 Uiso 1 1 calc R U . . . C2 C 0.6235(4) 0.2006(4) 0.2463(4) 0.0350(9) Uani 1 1 d . U . . . H2A H 0.6202 0.1699 0.3266 0.042 Uiso 1 1 calc R U . . . H2B H 0.7072 0.2483 0.2378 0.042 Uiso 1 1 calc R U . . . C1 C 0.6059(4) 0.0925(4) 0.1594(4) 0.0366(9) Uani 1 1 d . U . . . C9A C 0.4579(5) 0.0644(4) 0.1553(4) 0.0360(9) Uani 1 1 d . U . . . H9A H 0.4411 -0.0007 0.2151 0.043 Uiso 1 1 calc R U . . . C9 C 0.3956(6) 0.0131(4) 0.0413(4) 0.0506(12) Uani 1 1 d . U . . . H9B H 0.4212 0.0695 -0.0220 0.061 Uiso 1 1 calc R U . . . H9C H 0.4294 -0.0697 0.0262 0.061 Uiso 1 1 calc R U . . . C11 C 0.6795(6) -0.0202(5) 0.2011(5) 0.0548(13) Uani 1 1 d . U . . . H11A H 0.6496 -0.0469 0.2764 0.082 Uiso 1 1 calc R U . . . H11B H 0.7729 0.0026 0.2084 0.082 Uiso 1 1 calc R U . . . H11C H 0.6633 -0.0888 0.1453 0.082 Uiso 1 1 calc R U . . . C12 C 0.6569(6) 0.1347(5) 0.0426(4) 0.0530(12) Uani 1 1 d . U . . . H12A H 0.6478 0.0645 -0.0121 0.080 Uiso 1 1 calc R U . . . H12B H 0.7487 0.1628 0.0533 0.080 Uiso 1 1 calc R U . . . H12C H 0.6065 0.2035 0.0122 0.080 Uiso 1 1 calc R U . . . C113 C 0.8984(7) 0.8289(7) 0.5144(7) 0.078(2) Uani 1 1 d . U . . . H11D H 0.9233 0.7436 0.5308 0.118 Uiso 1 1 calc R U . . . H11E H 0.9764 0.8853 0.5164 0.118 Uiso 1 1 calc R U . . . H11F H 0.8536 0.8315 0.4377 0.118 Uiso 1 1 calc R U . . . C107 C 0.8075(6) 0.8701(5) 0.6055(5) 0.0566(13) Uani 1 1 d . U . . . C110 C 0.7009(5) 0.7677(4) 0.6213(4) 0.0417(10) Uani 1 1 d . U . . . H11G H 0.7407 0.6916 0.6518 0.050 Uiso 1 1 calc R U . . . H11H H 0.6560 0.7466 0.5455 0.050 Uiso 1 1 calc R U . . . C13A C 0.6020(4) 0.8103(3) 0.7047(3) 0.0321(8) Uani 1 1 d . U . . . C103 C 0.4859(4) 0.7167(3) 0.7152(3) 0.0295(8) Uani 1 1 d . U . . . H103 H 0.4680 0.6734 0.6392 0.035 Uiso 1 1 calc R U . . . N101 N 0.4989(4) 0.6226(3) 0.8044(3) 0.0328(7) Uani 1 1 d . U . . . H101 H 0.4851 0.6453 0.8755 0.039 Uiso 1 1 calc R U . . . C114 C 0.5295(4) 0.5063(4) 0.7887(3) 0.0320(8) Uani 1 1 d . U . . . N102 N 0.5606(4) 0.4716(3) 0.6853(3) 0.0341(7) Uani 1 1 d . U . . . C116 C 0.7753(5) 0.3648(4) 0.6422(4) 0.0403(10) Uani 1 1 d . U . . . C121 C 0.8565(7) 0.3473(8) 0.7344(6) 0.083(2) Uani 1 1 d . U . . . H121 H 0.8229 0.3215 0.8057 0.100 Uiso 1 1 calc R U . . . C120 C 0.9901(9) 0.3669(11) 0.7256(10) 0.107(3) Uani 1 1 d . U . . . H120 H 1.0474 0.3534 0.7908 0.128 Uiso 1 1 calc R U . . . C119 C 1.0388(7) 0.4053(7) 0.6244(9) 0.080(2) Uani 1 1 d . U . . . C106 C 0.8793(6) 0.8984(6) 0.7226(6) 0.0672(16) Uani 1 1 d . U . . . H106 H 0.9397 0.9732 0.7126 0.081 Uiso 1 1 calc R U . . . C105 C 0.7886(6) 0.9291(6) 0.8166(5) 0.0587(14) Uani 1 1 d . U . . . H10C H 0.8386 0.9332 0.8920 0.070 Uiso 1 1 calc R U . . . H10D H 0.7545 1.0124 0.8014 0.070 Uiso 1 1 calc R U . . . C104 C 0.6758(5) 0.8341(4) 0.8235(4) 0.0433(10) Uani 1 1 d . U . . . H10E H 0.6147 0.8639 0.8790 0.052 Uiso 1 1 calc R U . . . H10F H 0.7087 0.7544 0.8529 0.052 Uiso 1 1 calc R U . . . C108 C 0.7452(6) 0.9927(5) 0.5650(6) 0.0628(16) Uani 1 1 d . U . . . H10G H 0.7704 1.0595 0.6222 0.075 Uiso 1 1 calc R U . . . H10H H 0.7806 1.0184 0.4905 0.075 Uiso 1 1 calc R U . . . C109 C 0.5988(6) 0.9805(5) 0.5501(5) 0.0563(13) Uani 1 1 d . U . . . H10I H 0.5729 0.9226 0.4853 0.068 Uiso 1 1 calc R U . . . H10J H 0.5650 1.0630 0.5307 0.068 Uiso 1 1 calc R U . . . C19A C 0.5392(5) 0.9316(4) 0.6601(4) 0.0361(9) Uani 1 1 d . U . . . H19A H 0.5584 0.9970 0.7211 0.043 Uiso 1 1 calc R U . . . C101 C 0.3902(5) 0.9044(4) 0.6516(4) 0.0403(10) Uani 1 1 d . U . . . C102 C 0.3719(4) 0.7981(4) 0.7367(4) 0.0365(9) Uani 1 1 d . U . . . H10K H 0.2876 0.7512 0.7207 0.044 Uiso 1 1 calc R U . . . H10L H 0.3766 0.8295 0.8172 0.044 Uiso 1 1 calc R U . . . C115 C 0.5246(6) 0.4274(4) 0.8948(4) 0.0532(13) Uani 1 1 d . U . . . H11I H 0.4641 0.3549 0.8797 0.080 Uiso 1 1 calc R U . . . H11J H 0.4949 0.4766 0.9585 0.080 Uiso 1 1 calc R U . . . H11K H 0.6115 0.3990 0.9156 0.080 Uiso 1 1 calc R U . . . C117 C 0.8233(7) 0.4039(9) 0.5403(6) 0.088(2) Uani 1 1 d . U . . . H117 H 0.7655 0.4171 0.4753 0.106 Uiso 1 1 calc R U . . . C118 C 0.9547(9) 0.4243(11) 0.5316(8) 0.112(3) Uani 1 1 d . U . . . H118 H 0.9875 0.4518 0.4605 0.135 Uiso 1 1 calc R U . . . C112 C 0.3181(6) 1.0190(5) 0.6860(5) 0.0565(13) Uani 1 1 d . U . . . H11L H 0.3450 1.0431 0.7657 0.085 Uiso 1 1 calc R U . . . H11M H 0.2242 0.9988 0.6801 0.085 Uiso 1 1 calc R U . . . H11N H 0.3390 1.0884 0.6341 0.085 Uiso 1 1 calc R U . . . C111 C 0.3349(6) 0.8626(5) 0.5302(5) 0.0607(14) Uani 1 1 d . U . . . H11O H 0.3483 0.9308 0.4754 0.091 Uiso 1 1 calc R U . . . H11P H 0.2416 0.8407 0.5329 0.091 Uiso 1 1 calc R U . . . H11Q H 0.3796 0.7896 0.5054 0.091 Uiso 1 1 calc R U . . . C122 C 1.1784(12) 0.4224(13) 0.6131(13) 0.123(3) Uani 1 1 d . U . . . F101 F 1.2175(8) 0.5320(9) 0.5893(12) 0.196(4) Uani 1 1 d . U . . . F103 F 1.2333(7) 0.3482(10) 0.5559(12) 0.221(5) Uani 1 1 d . U . . . F102 F 1.2398(9) 0.4316(17) 0.7106(14) 0.260(6) Uani 1 1 d . U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0451(4) 0.1110(6) 0.1255(7) -0.0148(5) 0.0014(3) 0.0158(4) Br1A 0.0487(4) 0.1274(8) 0.1482(8) 0.0232(6) 0.0070(4) 0.0236(4) C22 0.055(4) 0.092(6) 0.136(7) 0.027(5) 0.027(5) 0.010(4) S1 0.0481(6) 0.0215(4) 0.0377(5) 0.0009(4) 0.0129(4) 0.0050(4) S101 0.0483(6) 0.0210(4) 0.0329(5) -0.0003(3) 0.0001(4) 0.0040(4) F3 0.065(4) 0.213(8) 0.354(13) 0.128(9) -0.026(5) 0.017(4) C13 0.070(4) 0.070(4) 0.092(5) 0.002(3) -0.041(4) -0.005(3) F1 0.082(4) 0.101(5) 0.489(17) 0.006(7) 0.027(7) -0.036(4) F2 0.052(4) 0.59(2) 0.219(10) -0.090(13) 0.032(5) -0.056(8) O2 0.063(2) 0.0230(14) 0.0579(19) -0.0052(13) 0.0096(16) 0.0002(14) O1 0.079(3) 0.0421(18) 0.0512(19) 0.0135(15) 0.0270(17) 0.0165(17) O102 0.076(3) 0.0234(14) 0.0470(17) 0.0045(12) 0.0097(16) 0.0018(15) O101 0.063(2) 0.0354(16) 0.0454(17) -0.0071(13) -0.0108(15) 0.0072(15) C18 0.058(4) 0.102(5) 0.077(4) -0.010(4) 0.025(3) 0.017(4) C19 0.047(3) 0.066(4) 0.085(4) 0.014(3) -0.001(3) 0.014(3) C20 0.066(4) 0.105(6) 0.088(5) -0.025(4) -0.029(4) 0.005(4) C21 0.069(4) 0.085(4) 0.058(3) -0.024(3) -0.001(3) 0.006(3) C16 0.050(3) 0.026(2) 0.042(2) 0.0051(16) 0.0059(19) 0.0066(18) N2 0.042(2) 0.0218(15) 0.0361(17) -0.0041(13) 0.0084(14) 0.0045(13) C14 0.031(2) 0.0243(17) 0.035(2) -0.0072(14) 0.0050(15) -0.0021(15) N1 0.0396(18) 0.0241(15) 0.0295(15) -0.0050(12) 0.0007(13) 0.0020(13) C3 0.036(2) 0.0199(16) 0.0295(17) -0.0036(13) 0.0023(15) 0.0024(15) C3A 0.042(2) 0.0192(17) 0.0363(19) -0.0008(14) -0.0009(16) 0.0010(15) C10 0.048(3) 0.029(2) 0.042(2) 0.0031(16) -0.0090(18) 0.0004(18) C7 0.053(3) 0.038(2) 0.060(3) 0.002(2) -0.017(2) -0.008(2) C8 0.075(4) 0.038(3) 0.064(3) -0.012(2) -0.022(3) -0.008(3) C6 0.045(3) 0.055(3) 0.074(3) -0.002(3) -0.008(2) -0.014(2) C5 0.049(3) 0.055(3) 0.062(3) 0.012(2) 0.005(2) -0.010(2) C4 0.040(2) 0.037(2) 0.040(2) 0.0012(17) 0.0022(17) 0.0004(18) C17 0.055(3) 0.079(4) 0.054(3) -0.019(3) 0.011(2) 0.003(3) C15 0.090(4) 0.028(2) 0.040(2) -0.0102(18) 0.004(2) 0.012(2) C2 0.035(2) 0.0263(18) 0.043(2) -0.0026(16) -0.0012(17) 0.0033(16) C1 0.044(2) 0.023(2) 0.044(2) -0.0006(16) 0.0065(18) 0.0109(17) C9A 0.051(3) 0.0188(18) 0.038(2) 0.0007(15) -0.0044(18) 0.0050(17) C9 0.068(3) 0.030(2) 0.053(3) -0.0145(19) -0.005(2) 0.005(2) C11 0.054(3) 0.039(3) 0.073(3) -0.001(2) -0.003(2) 0.022(2) C12 0.070(3) 0.040(2) 0.052(3) -0.004(2) 0.020(2) 0.012(2) C113 0.074(4) 0.072(4) 0.094(5) -0.011(3) 0.051(4) -0.005(3) C107 0.055(3) 0.045(3) 0.071(3) -0.005(2) 0.032(3) -0.004(2) C110 0.051(3) 0.0272(19) 0.049(2) -0.0071(17) 0.017(2) -0.0002(18) C13A 0.040(2) 0.0225(17) 0.0349(19) -0.0029(14) 0.0061(16) 0.0052(16) C103 0.039(2) 0.0202(16) 0.0305(18) 0.0007(13) 0.0050(15) 0.0037(15) N101 0.045(2) 0.0245(15) 0.0289(15) 0.0004(12) 0.0060(14) 0.0002(14) C114 0.036(2) 0.0261(18) 0.0339(19) 0.0024(14) 0.0053(16) 0.0011(15) N102 0.048(2) 0.0209(15) 0.0334(16) 0.0016(13) 0.0058(15) 0.0020(14) C116 0.048(3) 0.030(2) 0.043(2) -0.0045(17) 0.0004(19) 0.0076(18) C121 0.057(4) 0.119(6) 0.073(4) 0.024(4) -0.006(3) 0.011(4) C120 0.060(5) 0.143(8) 0.118(7) 0.018(6) -0.013(5) 0.022(5) C119 0.048(4) 0.062(4) 0.129(7) -0.019(4) 0.012(4) 0.001(3) C106 0.045(3) 0.058(3) 0.099(5) 0.001(3) 0.018(3) -0.007(3) C105 0.050(3) 0.060(3) 0.065(3) -0.015(3) 0.002(2) -0.009(3) C104 0.043(3) 0.046(2) 0.040(2) -0.0078(19) 0.0024(18) -0.002(2) C108 0.077(4) 0.043(3) 0.071(4) 0.007(2) 0.035(3) -0.007(3) C109 0.081(4) 0.034(2) 0.057(3) 0.013(2) 0.021(3) 0.005(2) C19A 0.051(3) 0.0183(18) 0.040(2) -0.0043(15) 0.0110(18) 0.0016(17) C101 0.050(3) 0.025(2) 0.046(2) -0.0027(17) -0.0018(19) 0.0097(18) C102 0.036(2) 0.0287(19) 0.045(2) -0.0007(16) 0.0048(17) 0.0061(17) C115 0.094(4) 0.034(2) 0.034(2) 0.0067(18) 0.015(2) 0.013(2) C117 0.057(4) 0.147(8) 0.058(3) 0.011(4) 0.008(3) -0.015(4) C118 0.083(6) 0.163(9) 0.092(6) 0.002(6) 0.041(5) -0.022(6) C112 0.059(3) 0.035(2) 0.076(4) -0.006(2) -0.003(3) 0.019(2) C111 0.075(4) 0.049(3) 0.057(3) -0.001(2) -0.016(3) 0.012(3) C122 0.098(6) 0.123(6) 0.149(6) -0.024(5) 0.018(5) 0.002(5) F101 0.112(5) 0.167(7) 0.312(10) -0.008(7) 0.070(6) -0.033(5) F103 0.087(4) 0.231(8) 0.350(11) -0.118(8) 0.064(6) 0.010(5) F102 0.093(6) 0.428(14) 0.252(10) 0.026(10) -0.004(6) -0.046(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F3 C22 C19 113.7(8) . . ? F1 C22 F3 102.9(12) . . ? F1 C22 C19 114.8(8) . . ? F2 C22 F3 104.0(12) . . ? F2 C22 F1 103.5(12) . . ? F2 C22 C19 116.3(10) . . ? O2 S1 O1 116.6(2) . . ? O2 S1 C16 106.7(2) . . ? O2 S1 N2 115.6(2) . . ? O1 S1 C16 106.3(2) . . ? O1 S1 N2 106.60(19) . . ? N2 S1 C16 103.94(19) . . ? O102 S101 O101 116.3(2) . . ? O102 S101 N102 116.42(19) . . ? O102 S101 C116 106.5(2) . . ? O101 S101 N102 107.04(19) . . ? O101 S101 C116 106.5(2) . . ? N102 S101 C116 102.7(2) . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C7 C13 H13A 109.5 . . ? C7 C13 H13B 109.5 . . ? C7 C13 H13C 109.5 . . ? C19 C18 H18 119.1 . . ? C19 C18 C17 121.8(6) . . ? C17 C18 H18 119.1 . . ? C18 C19 C22 120.5(7) . . ? C18 C19 C20 119.1(6) . . ? C20 C19 C22 120.4(7) . . ? C19 C20 H20 119.5 . . ? C21 C20 C19 121.0(6) . . ? C21 C20 H20 119.5 . . ? C20 C21 H21 120.8 . . ? C20 C21 C16 118.4(6) . . ? C16 C21 H21 120.8 . . ? C21 C16 S1 119.6(4) . . ? C21 C16 C17 120.9(5) . . ? C17 C16 S1 119.4(4) . . ? C14 N2 S1 123.1(3) . . ? N2 C14 N1 118.4(3) . . ? N2 C14 C15 127.4(4) . . ? N1 C14 C15 114.2(4) . . ? C14 N1 H1 117.1 . . ? C14 N1 C3 125.9(3) . . ? C3 N1 H1 117.1 . . ? N1 C3 H3 108.7 . . ? N1 C3 C3A 115.4(3) . . ? N1 C3 C2 110.8(3) . . ? C3A C3 H3 108.7 . . ? C2 C3 H3 108.7 . . ? C2 C3 C3A 104.4(3) . . ? C3 C3A C9A 103.1(3) . . ? C10 C3A C3 112.2(3) . . ? C10 C3A C4 108.2(4) . . ? C10 C3A C9A 110.6(3) . . ? C4 C3A C3 111.2(3) . . ? C4 C3A C9A 111.6(3) . . ? C3A C10 H10A 109.6 . . ? C3A C10 H10B 109.6 . . ? C3A C10 C7 110.2(4) . . ? H10A C10 H10B 108.1 . . ? C7 C10 H10A 109.6 . . ? C7 C10 H10B 109.6 . . ? C13 C7 C8 108.6(5) . . ? C10 C7 C13 109.4(4) . . ? C10 C7 C8 110.0(5) . . ? C6 C7 C13 112.2(6) . . ? C6 C7 C10 109.0(4) . . ? C6 C7 C8 107.7(4) . . ? C7 C8 H8A 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C9 C8 C7 113.0(4) . . ? C9 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? Br1 C6 H6 107.9 . . ? C7 C6 Br1 112.5(4) . . ? C7 C6 H6 107.9 . . ? C7 C6 C5 112.9(5) . . ? C5 C6 Br1 107.6(4) . . ? C5 C6 H6 107.9 . . ? C6 C5 H5A 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? C4 C5 C6 111.6(4) . . ? C4 C5 H5A 109.3 . . ? C4 C5 H5B 109.3 . . ? C3A C4 H4A 109.1 . . ? C3A C4 H4B 109.1 . . ? C5 C4 C3A 112.5(4) . . ? C5 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? C18 C17 H17 120.6 . . ? C16 C17 C18 118.7(6) . . ? C16 C17 H17 120.6 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C3 C2 H2A 111.1 . . ? C3 C2 H2B 111.1 . . ? C3 C2 C1 103.5(3) . . ? H2A C2 H2B 109.0 . . ? C1 C2 H2A 111.1 . . ? C1 C2 H2B 111.1 . . ? C2 C1 C9A 102.1(3) . . ? C2 C1 C12 109.7(4) . . ? C9A C1 C12 113.5(4) . . ? C11 C1 C2 111.5(4) . . ? C11 C1 C9A 111.5(4) . . ? C11 C1 C12 108.5(4) . . ? C3A C9A H9A 106.8 . . ? C1 C9A C3A 108.0(3) . . ? C1 C9A H9A 106.8 . . ? C9 C9A C3A 111.8(4) . . ? C9 C9A C1 116.3(4) . . ? C9 C9A H9A 106.8 . . ? C8 C9 C9A 113.0(4) . . ? C8 C9 H9B 109.0 . . ? C8 C9 H9C 109.0 . . ? C9A C9 H9B 109.0 . . ? C9A C9 H9C 109.0 . . ? H9B C9 H9C 107.8 . . ? C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 C12 H12A 109.5 . . ? C1 C12 H12B 109.5 . . ? C1 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? H11D C113 H11E 109.5 . . ? H11D C113 H11F 109.5 . . ? H11E C113 H11F 109.5 . . ? C107 C113 H11D 109.5 . . ? C107 C113 H11E 109.5 . . ? C107 C113 H11F 109.5 . . ? C113 C107 C108 109.1(5) . . ? C110 C107 C113 109.7(4) . . ? C110 C107 C108 109.8(5) . . ? C106 C107 C113 112.5(6) . . ? C106 C107 C110 108.9(4) . . ? C106 C107 C108 106.8(5) . . ? C107 C110 H11G 109.5 . . ? C107 C110 H11H 109.5 . . ? C107 C110 C13A 110.9(4) . . ? H11G C110 H11H 108.0 . . ? C13A C110 H11G 109.5 . . ? C13A C110 H11H 109.5 . . ? C110 C13A C103 113.4(3) . . ? C110 C13A C104 107.2(4) . . ? C110 C13A C19A 110.7(3) . . ? C103 C13A C104 111.0(3) . . ? C103 C13A C19A 103.9(3) . . ? C104 C13A C19A 110.6(3) . . ? C13A C103 H103 108.3 . . ? N101 C103 C13A 116.5(3) . . ? N101 C103 H103 108.3 . . ? N101 C103 C102 110.7(3) . . ? C102 C103 C13A 104.3(3) . . ? C102 C103 H103 108.3 . . ? C103 N101 H101 117.0 . . ? C114 N101 C103 126.0(3) . . ? C114 N101 H101 117.0 . . ? N101 C114 C115 114.2(4) . . ? N102 C114 N101 118.7(3) . . ? N102 C114 C115 127.2(4) . . ? C114 N102 S101 124.5(3) . . ? C121 C116 S101 119.2(5) . . ? C121 C116 C117 120.1(6) . . ? C117 C116 S101 120.7(4) . . ? C116 C121 H121 120.0 . . ? C116 C121 C120 120.0(7) . . ? C120 C121 H121 120.0 . . ? C121 C120 H120 119.8 . . ? C119 C120 C121 120.4(8) . . ? C119 C120 H120 119.8 . . ? C120 C119 C118 118.9(7) . . ? C120 C119 C122 120.9(10) . . ? C118 C119 C122 120.1(10) . . ? Br1A C106 H106 107.6 . . ? C107 C106 Br1A 112.4(4) . . ? C107 C106 H106 107.6 . . ? C107 C106 C105 113.1(5) . . ? C105 C106 Br1A 108.3(5) . . ? C105 C106 H106 107.6 . . ? C106 C105 H10C 109.1 . . ? C106 C105 H10D 109.1 . . ? H10C C105 H10D 107.8 . . ? C104 C105 C106 112.7(5) . . ? C104 C105 H10C 109.1 . . ? C104 C105 H10D 109.1 . . ? C13A C104 H10E 109.1 . . ? C13A C104 H10F 109.1 . . ? C105 C104 C13A 112.3(4) . . ? C105 C104 H10E 109.1 . . ? C105 C104 H10F 109.1 . . ? H10E C104 H10F 107.9 . . ? C107 C108 H10G 108.9 . . ? C107 C108 H10H 108.9 . . ? H10G C108 H10H 107.7 . . ? C109 C108 C107 113.4(4) . . ? C109 C108 H10G 108.9 . . ? C109 C108 H10H 108.9 . . ? C108 C109 H10I 109.4 . . ? C108 C109 H10J 109.4 . . ? C108 C109 C19A 111.2(5) . . ? H10I C109 H10J 108.0 . . ? C19A C109 H10I 109.4 . . ? C19A C109 H10J 109.4 . . ? C13A C19A H19A 107.1 . . ? C109 C19A C13A 112.0(4) . . ? C109 C19A H19A 107.1 . . ? C109 C19A C101 115.8(4) . . ? C101 C19A C13A 107.3(3) . . ? C101 C19A H19A 107.1 . . ? C19A C101 C111 114.1(4) . . ? C102 C101 C19A 102.6(3) . . ? C102 C101 C112 111.6(4) . . ? C102 C101 C111 109.8(4) . . ? C112 C101 C19A 111.4(4) . . ? C112 C101 C111 107.4(4) . . ? C103 C102 H10K 111.2 . . ? C103 C102 H10L 111.2 . . ? C101 C102 C103 103.0(3) . . ? C101 C102 H10K 111.2 . . ? C101 C102 H10L 111.2 . . ? H10K C102 H10L 109.1 . . ? C114 C115 H11I 109.5 . . ? C114 C115 H11J 109.5 . . ? C114 C115 H11K 109.5 . . ? H11I C115 H11J 109.5 . . ? H11I C115 H11K 109.5 . . ? H11J C115 H11K 109.5 . . ? C116 C117 H117 119.9 . . ? C116 C117 C118 120.1(7) . . ? C118 C117 H117 119.9 . . ? C119 C118 C117 120.5(8) . . ? C119 C118 H118 119.8 . . ? C117 C118 H118 119.8 . . ? C101 C112 H11L 109.5 . . ? C101 C112 H11M 109.5 . . ? C101 C112 H11N 109.5 . . ? H11L C112 H11M 109.5 . . ? H11L C112 H11N 109.5 . . ? H11M C112 H11N 109.5 . . ? C101 C111 H11O 109.5 . . ? C101 C111 H11P 109.5 . . ? C101 C111 H11Q 109.5 . . ? H11O C111 H11P 109.5 . . ? H11O C111 H11Q 109.5 . . ? H11P C111 H11Q 109.5 . . ? F101 C122 C119 114.7(11) . . ? F101 C122 F103 109.8(14) . . ? F101 C122 F102 90.0(12) . . ? F103 C122 C119 119.4(11) . . ? F103 C122 F102 107.3(14) . . ? F102 C122 C119 111.7(13) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C6 1.987(7) . ? Br1A C106 1.975(7) . ? C22 F3 1.254(12) . ? C22 F1 1.225(12) . ? C22 F2 1.183(14) . ? C22 C19 1.484(10) . ? S1 O2 1.431(3) . ? S1 O1 1.436(4) . ? S1 C16 1.765(5) . ? S1 N2 1.598(3) . ? S101 O102 1.434(3) . ? S101 O101 1.433(3) . ? S101 N102 1.591(3) . ? S101 C116 1.760(5) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C13 C7 1.534(8) . ? C18 H18 0.9500 . ? C18 C19 1.322(10) . ? C18 C17 1.386(9) . ? C19 C20 1.409(11) . ? C20 H20 0.9500 . ? C20 C21 1.363(10) . ? C21 H21 0.9500 . ? C21 C16 1.382(8) . ? C16 C17 1.378(7) . ? N2 C14 1.306(5) . ? C14 N1 1.318(5) . ? C14 C15 1.499(6) . ? N1 H1 0.8800 . ? N1 C3 1.460(5) . ? C3 H3 1.0000 . ? C3 C3A 1.540(6) . ? C3 C2 1.525(6) . ? C3A C10 1.526(6) . ? C3A C4 1.530(6) . ? C3A C9A 1.575(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C10 C7 1.529(7) . ? C7 C8 1.577(8) . ? C7 C6 1.532(9) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C9 1.484(9) . ? C6 H6 1.0000 . ? C6 C5 1.538(8) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C4 1.518(7) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C17 H17 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C1 1.531(6) . ? C1 C9A 1.538(7) . ? C1 C11 1.528(6) . ? C1 C12 1.540(7) . ? C9A H9A 1.0000 . ? C9A C9 1.526(6) . ? C9 H9B 0.9900 . ? C9 H9C 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C113 H11D 0.9800 . ? C113 H11E 0.9800 . ? C113 H11F 0.9800 . ? C113 C107 1.531(8) . ? C107 C110 1.531(7) . ? C107 C106 1.532(10) . ? C107 C108 1.556(9) . ? C110 H11G 0.9900 . ? C110 H11H 0.9900 . ? C110 C13A 1.531(6) . ? C13A C103 1.531(6) . ? C13A C104 1.550(6) . ? C13A C19A 1.560(6) . ? C103 H103 1.0000 . ? C103 N101 1.453(5) . ? C103 C102 1.533(6) . ? N101 H101 0.8800 . ? N101 C114 1.317(5) . ? C114 N102 1.317(5) . ? C114 C115 1.495(6) . ? C116 C121 1.340(8) . ? C116 C117 1.364(9) . ? C121 H121 0.9500 . ? C121 C120 1.392(12) . ? C120 H120 0.9500 . ? C120 C119 1.358(14) . ? C119 C118 1.367(13) . ? C119 C122 1.456(14) . ? C106 H106 1.0000 . ? C106 C105 1.523(9) . ? C105 H10C 0.9900 . ? C105 H10D 0.9900 . ? C105 C104 1.511(7) . ? C104 H10E 0.9900 . ? C104 H10F 0.9900 . ? C108 H10G 0.9900 . ? C108 H10H 0.9900 . ? C108 C109 1.509(9) . ? C109 H10I 0.9900 . ? C109 H10J 0.9900 . ? C109 C19A 1.528(6) . ? C19A H19A 1.0000 . ? C19A C101 1.547(7) . ? C101 C102 1.519(6) . ? C101 C112 1.534(6) . ? C101 C111 1.546(7) . ? C102 H10K 0.9900 . ? C102 H10L 0.9900 . ? C115 H11I 0.9800 . ? C115 H11J 0.9800 . ? C115 H11K 0.9800 . ? C117 H117 0.9500 . ? C117 C118 1.371(11) . ? C118 H118 0.9500 . ? C112 H11L 0.9800 . ? C112 H11M 0.9800 . ? C112 H11N 0.9800 . ? C111 H11O 0.9800 . ? C111 H11P 0.9800 . ? C111 H11Q 0.9800 . ? C122 F101 1.258(16) . ? C122 F103 1.217(15) . ? C122 F102 1.266(17) . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br1 C6 C5 C4 -74.6(5) . . . . ? Br1A C106 C105 C104 -75.4(6) . . . . ? C22 C19 C20 C21 -179.4(7) . . . . ? S1 C16 C17 C18 -178.7(5) . . . . ? S1 N2 C14 N1 176.5(3) . . . . ? S1 N2 C14 C15 -4.7(7) . . . . ? S101 C116 C121 C120 179.0(7) . . . . ? S101 C116 C117 C118 -179.5(8) . . . . ? F3 C22 C19 C18 110.0(12) . . . . ? F3 C22 C19 C20 -70.8(13) . . . . ? C13 C7 C8 C9 120.3(6) . . . . ? C13 C7 C6 Br1 -53.7(5) . . . . ? C13 C7 C6 C5 -175.7(5) . . . . ? F1 C22 C19 C18 -131.8(12) . . . . ? F1 C22 C19 C20 47.3(14) . . . . ? F2 C22 C19 C18 -10.8(16) . . . . ? F2 C22 C19 C20 168.3(14) . . . . ? O2 S1 C16 C21 162.3(5) . . . . ? O2 S1 C16 C17 -19.6(5) . . . . ? O2 S1 N2 C14 26.0(4) . . . . ? O1 S1 C16 C21 37.2(5) . . . . ? O1 S1 C16 C17 -144.7(4) . . . . ? O1 S1 N2 C14 157.4(4) . . . . ? O102 S101 N102 C114 11.1(5) . . . . ? O102 S101 C116 C121 -29.0(6) . . . . ? O102 S101 C116 C117 151.1(6) . . . . ? O101 S101 N102 C114 143.2(4) . . . . ? O101 S101 C116 C121 -153.8(5) . . . . ? O101 S101 C116 C117 26.3(6) . . . . ? C18 C19 C20 C21 -0.3(12) . . . . ? C19 C18 C17 C16 -0.1(11) . . . . ? C19 C20 C21 C16 -0.3(12) . . . . ? C20 C21 C16 S1 178.9(6) . . . . ? C20 C21 C16 C17 0.8(10) . . . . ? C21 C16 C17 C18 -0.6(9) . . . . ? C16 S1 N2 C14 -90.5(4) . . . . ? N2 S1 C16 C21 -75.1(5) . . . . ? N2 S1 C16 C17 103.0(5) . . . . ? N2 C14 N1 C3 2.0(6) . . . . ? C14 N1 C3 C3A -99.3(4) . . . . ? C14 N1 C3 C2 142.4(4) . . . . ? N1 C3 C3A C10 91.5(4) . . . . ? N1 C3 C3A C4 -29.8(5) . . . . ? N1 C3 C3A C9A -149.5(3) . . . . ? N1 C3 C2 C1 168.4(3) . . . . ? C3 C3A C10 C7 174.1(4) . . . . ? C3 C3A C4 C5 -178.2(4) . . . . ? C3 C3A C9A C1 2.5(4) . . . . ? C3 C3A C9A C9 -126.7(4) . . . . ? C3 C2 C1 C9A -40.6(4) . . . . ? C3 C2 C1 C11 -159.7(4) . . . . ? C3 C2 C1 C12 80.0(4) . . . . ? C3A C3 C2 C1 43.5(4) . . . . ? C3A C10 C7 C13 -175.8(5) . . . . ? C3A C10 C7 C8 -56.6(5) . . . . ? C3A C10 C7 C6 61.2(6) . . . . ? C3A C9A C9 C8 -49.5(5) . . . . ? C10 C3A C4 C5 58.1(5) . . . . ? C10 C3A C9A C1 122.5(4) . . . . ? C10 C3A C9A C9 -6.6(5) . . . . ? C10 C7 C8 C9 0.6(6) . . . . ? C10 C7 C6 Br1 67.7(5) . . . . ? C10 C7 C6 C5 -54.4(6) . . . . ? C7 C8 C9 C9A 52.9(6) . . . . ? C7 C6 C5 C4 50.1(7) . . . . ? C8 C7 C6 Br1 -173.0(3) . . . . ? C8 C7 C6 C5 64.9(5) . . . . ? C6 C7 C8 C9 -118.0(5) . . . . ? C6 C5 C4 C3A -51.9(6) . . . . ? C4 C3A C10 C7 -62.8(5) . . . . ? C4 C3A C9A C1 -117.0(4) . . . . ? C4 C3A C9A C9 113.9(4) . . . . ? C17 C18 C19 C22 179.6(7) . . . . ? C17 C18 C19 C20 0.5(12) . . . . ? C15 C14 N1 C3 -176.9(4) . . . . ? C2 C3 C3A C10 -146.6(4) . . . . ? C2 C3 C3A C4 92.0(4) . . . . ? C2 C3 C3A C9A -27.7(4) . . . . ? C2 C1 C9A C3A 23.3(4) . . . . ? C2 C1 C9A C9 149.8(4) . . . . ? C1 C9A C9 C8 -174.2(4) . . . . ? C9A C3A C10 C7 59.7(5) . . . . ? C9A C3A C4 C5 -63.7(5) . . . . ? C11 C1 C9A C3A 142.4(4) . . . . ? C11 C1 C9A C9 -91.0(5) . . . . ? C12 C1 C9A C3A -94.7(4) . . . . ? C12 C1 C9A C9 31.9(5) . . . . ? C113 C107 C110 C13A -175.4(5) . . . . ? C113 C107 C106 Br1A -52.3(6) . . . . ? C113 C107 C106 C105 -175.3(5) . . . . ? C113 C107 C108 C109 119.5(6) . . . . ? C107 C110 C13A C103 174.5(4) . . . . ? C107 C110 C13A C104 -62.6(5) . . . . ? C107 C110 C13A C19A 58.2(5) . . . . ? C107 C106 C105 C104 49.9(7) . . . . ? C107 C108 C109 C19A 54.4(6) . . . . ? C110 C107 C106 Br1A 69.5(5) . . . . ? C110 C107 C106 C105 -53.5(6) . . . . ? C110 C107 C108 C109 -0.7(7) . . . . ? C110 C13A C103 N101 90.1(4) . . . . ? C110 C13A C103 C102 -147.6(4) . . . . ? C110 C13A C104 C105 57.4(5) . . . . ? C110 C13A C19A C109 -3.8(5) . . . . ? C110 C13A C19A C101 124.3(4) . . . . ? C13A C103 N101 C114 -99.7(5) . . . . ? C13A C103 C102 C101 43.0(4) . . . . ? C13A C19A C101 C102 23.7(4) . . . . ? C13A C19A C101 C112 143.2(4) . . . . ? C13A C19A C101 C111 -95.0(4) . . . . ? C103 C13A C104 C105 -178.2(4) . . . . ? C103 C13A C19A C109 -125.9(4) . . . . ? C103 C13A C19A C101 2.2(4) . . . . ? C103 N101 C114 N102 5.1(6) . . . . ? C103 N101 C114 C115 -175.0(4) . . . . ? N101 C103 C102 C101 169.1(3) . . . . ? N101 C114 N102 S101 176.5(3) . . . . ? N102 S101 C116 C121 93.8(6) . . . . ? N102 S101 C116 C117 -86.0(6) . . . . ? C116 S101 N102 C114 -104.8(4) . . . . ? C116 C121 C120 C119 0.8(15) . . . . ? C116 C117 C118 C119 0.2(16) . . . . ? C121 C116 C117 C118 0.7(13) . . . . ? C121 C120 C119 C118 0.0(15) . . . . ? C121 C120 C119 C122 -178.1(10) . . . . ? C120 C119 C118 C117 -0.5(15) . . . . ? C120 C119 C122 F101 -118.7(14) . . . . ? C120 C119 C122 F103 108.0(16) . . . . ? C120 C119 C122 F102 -18.1(18) . . . . ? C106 C107 C110 C13A 61.1(6) . . . . ? C106 C107 C108 C109 -118.7(5) . . . . ? C106 C105 C104 C13A -51.9(7) . . . . ? C104 C13A C103 N101 -30.7(5) . . . . ? C104 C13A C103 C102 91.7(4) . . . . ? C104 C13A C19A C109 114.9(4) . . . . ? C104 C13A C19A C101 -117.0(4) . . . . ? C108 C107 C110 C13A -55.6(6) . . . . ? C108 C107 C106 Br1A -171.9(3) . . . . ? C108 C107 C106 C105 65.1(6) . . . . ? C108 C109 C19A C13A -51.5(6) . . . . ? C108 C109 C19A C101 -174.9(4) . . . . ? C109 C19A C101 C102 149.6(4) . . . . ? C109 C19A C101 C112 -90.9(5) . . . . ? C109 C19A C101 C111 30.9(5) . . . . ? C19A C13A C103 N101 -149.6(3) . . . . ? C19A C13A C103 C102 -27.3(4) . . . . ? C19A C13A C104 C105 -63.4(5) . . . . ? C19A C101 C102 C103 -40.5(4) . . . . ? C102 C103 N101 C114 141.4(4) . . . . ? C115 C114 N102 S101 -3.3(7) . . . . ? C117 C116 C121 C120 -1.1(13) . . . . ? C118 C119 C122 F101 63.2(16) . . . . ? C118 C119 C122 F103 -70.1(18) . . . . ? C118 C119 C122 F102 163.8(14) . . . . ? C112 C101 C102 C103 -159.9(4) . . . . ? C111 C101 C102 C103 81.1(5) . . . . ? C122 C119 C118 C117 177.6(10) . . . . ?