#------------------------------------------------------------------------------ #$Date: 2026-03-04 22:02:50 +0000 (Wed, 04 Mar 2026) $ #$Revision: 304785 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064318.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_7064318 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 F3 I N2 O2 S' _chemical_formula_sum 'C24 H32 F3 I N2 O2 S' _chemical_formula_weight 596.47 _chemical_melting_point 466.6 _chemical_name_systematic N-(6-iodo-1,1,7-trimethyldecahydro-3a,7-methanocyclopenta[8]annulen-3-yl)-N'-((4-(trifluoromethyl)phenyl)sulfonyl)acetimidamide _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 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 _cell_angle_beta 95.162(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.5276(11) _cell_length_b 11.5823(12) _cell_length_c 10.7820(12) _cell_measurement_reflns_used 9979 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.36 _cell_measurement_theta_min 2.59 _cell_volume 1309.4(2) _computing_cell_refinement 'SAINT V8.32B (BRUKER, 2016)' _computing_data_collection 'Bruker APEX3' _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 1.000 _diffrn_measured_fraction_theta_max 0.997 _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 0.0518 _diffrn_reflns_av_unetI/netI 0.0470 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 27070 _diffrn_reflns_point_group_measured_fraction_full 0.972 _diffrn_reflns_point_group_measured_fraction_max 0.944 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.479 _diffrn_reflns_theta_min 1.896 _diffrn_source_current 1.0 _diffrn_source_power 0.05 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.347 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.4410 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1715 before and 0.0811 after correction. The Ratio of minimum to maximum transmission is 0.5915. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.513 _exptl_crystal_description needle _exptl_crystal_F_000 604 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: dichlormetan-methanol' _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.345 _exptl_crystal_size_min 0.255 _refine_diff_density_max 0.557 _refine_diff_density_min -0.788 _refine_diff_density_rms 0.123 _refine_ls_abs_structure_details ; Flack x determined using 1839 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.011(9) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 302 _refine_ls_number_reflns 5668 _refine_ls_number_restraints 19 _refine_ls_restrained_S_all 1.157 _refine_ls_R_factor_all 0.0578 _refine_ls_R_factor_gt 0.0436 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0735P)^2^+0.1300P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1122 _refine_ls_wR_factor_ref 0.1204 _reflns_Friedel_coverage 0.803 _reflns_Friedel_fraction_full 0.941 _reflns_Friedel_fraction_max 0.885 _reflns_number_gt 4641 _reflns_number_total 5668 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5nj03976b2.cif _cod_data_source_block 4h _cod_database_code 7064318 _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 0.725 _shelx_estimated_absorpt_t_min 0.499 _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(F3) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1 Uanis(F2) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1 Uanis(F3) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F1) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01 Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1 3.a Ternary CH refined with riding coordinates: C6(H6), C3(H3), C9A(H9A) 3.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C5(H5A,H5B), C4(H4A,H4B), C9(H9B,H9C), C8(H8A,H8B), C10(H10A,H10B) 3.c Aromatic/amide H refined with riding coordinates: N1(H1), C17(H17), C18(H18), C20(H20), C21(H21) 3.d Idealised Me refined as rotating group: C15(H15A,H15B,H15C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C12(H12A,H12B, H12C) ; _shelx_res_file ; TITL 01_a.res in P2(1) CELL 0.71073 10.5276 11.5823 10.782 90 95.162 90 ZERR 2 0.0011 0.0012 0.0012 0 0.003 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O F S I UNIT 48 64 4 4 6 2 2 ISOR 0.05 0.1 F3 ISOR 0.05 0.1 F2 ISOR 0.005 0.01 F3 F2 F1 ISOR 0.05 0.1 F2 F3 F1 L.S. 50 PLAN 8 SIZE 0.255 0.345 0.6 TEMP 0 CONF BOND $H MORE -1 HTAB fmap 2 acta REM REM REM WGHT 0.073500 0.130000 FVAR 0.48092 I1 7 0.488386 0.421190 0.763710 11.00000 0.04519 0.15150 = 0.10446 -0.01088 0.02031 -0.00401 S1 6 0.108261 0.536421 0.341857 11.00000 0.05641 0.03634 = 0.02338 0.00231 0.00844 0.00860 O1 4 0.075101 0.453205 0.245593 11.00000 0.07262 0.05803 = 0.02442 -0.00368 0.00446 0.00096 N1 3 0.002130 0.386073 0.625737 11.00000 0.04362 0.03080 = 0.02573 -0.00177 0.00412 -0.00241 AFIX 43 H1 2 -0.013150 0.316323 0.647352 11.00000 -1.20000 AFIX 0 N2 3 0.063527 0.507008 0.476112 11.00000 0.05086 0.03483 = 0.02351 -0.00312 0.00716 0.00418 O2 4 0.071736 0.653961 0.315198 11.00000 0.08915 0.04453 = 0.04122 0.00990 0.02075 0.02396 C3A 1 0.104552 0.490533 0.816162 11.00000 0.04363 0.03497 = 0.02152 0.00067 0.00557 -0.00391 C2 1 -0.122841 0.451128 0.795088 11.00000 0.03912 0.04431 = 0.02724 0.00051 0.00686 -0.00057 AFIX 23 H2A 2 -0.203479 0.463699 0.746023 11.00000 -1.20000 H2B 2 -0.119914 0.372324 0.825666 11.00000 -1.20000 AFIX 0 C6 1 0.375405 0.483527 0.913108 11.00000 0.03977 0.09238 = 0.04696 0.00360 -0.00252 -0.01752 AFIX 13 H6 2 0.434234 0.496229 0.987577 11.00000 -1.20000 AFIX 0 C5 1 0.284993 0.385509 0.941758 11.00000 0.04697 0.06063 = 0.04702 0.01362 -0.00498 -0.00250 AFIX 23 H5A 2 0.331922 0.313348 0.947316 11.00000 -1.20000 H5B 2 0.252692 0.399603 1.021853 11.00000 -1.20000 AFIX 0 C4 1 0.173186 0.374603 0.842468 11.00000 0.03914 0.03911 = 0.03886 0.00397 0.00397 -0.00358 AFIX 23 H4A 2 0.112882 0.318742 0.869634 11.00000 -1.20000 H4B 2 0.204021 0.346053 0.766095 11.00000 -1.20000 AFIX 0 C3 1 -0.010649 0.476149 0.718812 11.00000 0.04009 0.02959 = 0.02242 -0.00220 0.00509 0.00078 AFIX 13 H3 2 -0.026202 0.549922 0.675587 11.00000 -1.20000 AFIX 0 C14 1 0.034987 0.401839 0.511431 11.00000 0.03744 0.03604 = 0.02246 -0.00464 0.00244 -0.00027 C16 1 0.277646 0.536158 0.366554 11.00000 0.05579 0.04426 = 0.03111 0.00382 0.01489 -0.00065 C17 1 0.345304 0.445300 0.327056 11.00000 0.05923 0.05634 = 0.07568 -0.01077 0.01426 0.01037 AFIX 43 H17 2 0.302464 0.382250 0.289871 11.00000 -1.20000 AFIX 0 C18 1 0.476609 0.445779 0.341596 11.00000 0.06438 0.10166 = 0.09085 -0.01185 0.01903 0.02353 AFIX 43 H18 2 0.522331 0.384263 0.312503 11.00000 -1.20000 AFIX 0 C19 1 0.538784 0.536486 0.398583 11.00000 0.06182 0.10343 = 0.06749 0.01969 0.00872 -0.00350 C22 1 0.678976 0.533380 0.409590 11.00000 0.05704 0.20064 = 0.10110 0.04567 0.00617 0.02415 C15 1 0.035108 0.293102 0.434699 11.00000 0.09228 0.03598 = 0.04117 -0.00995 0.01423 -0.00589 AFIX 137 H15A 2 0.020852 0.227684 0.486334 11.00000 -1.50000 H15B 2 0.116004 0.285073 0.401003 11.00000 -1.50000 H15C 2 -0.031453 0.297275 0.367877 11.00000 -1.50000 AFIX 0 C20 1 0.471959 0.628688 0.439404 11.00000 0.08046 0.08636 = 0.09262 -0.00989 0.00571 -0.02729 AFIX 43 H20 2 0.515301 0.690982 0.477643 11.00000 -1.20000 AFIX 0 C21 1 0.340435 0.628844 0.423644 11.00000 0.07537 0.05991 = 0.08171 -0.01433 0.01189 -0.01426 AFIX 43 H21 2 0.294648 0.690962 0.451320 11.00000 -1.20000 AFIX 0 C1 1 -0.104667 0.537082 0.902175 11.00000 0.05181 0.04305 = 0.02378 0.00158 0.01062 0.00514 C11 1 -0.176401 0.500742 1.013331 11.00000 0.05951 0.07110 = 0.03452 0.00150 0.02072 0.00061 AFIX 137 H11A 2 -0.266496 0.501567 0.989579 11.00000 -1.50000 H11B 2 -0.157052 0.553604 1.080978 11.00000 -1.50000 H11C 2 -0.150607 0.424281 1.039096 11.00000 -1.50000 AFIX 0 C9A 1 0.041995 0.534476 0.934665 11.00000 0.05370 0.03728 = 0.01904 0.00144 0.00642 -0.00670 AFIX 13 H9A 2 0.058935 0.475429 0.999134 11.00000 -1.20000 AFIX 0 C9 1 0.103215 0.646178 0.986508 11.00000 0.07949 0.05035 = 0.03550 -0.01276 0.00631 -0.02034 AFIX 23 H9B 2 0.079302 0.709340 0.930100 11.00000 -1.20000 H9C 2 0.071595 0.663495 1.066205 11.00000 -1.20000 AFIX 0 C8 1 0.246309 0.636168 1.002832 11.00000 0.08027 0.07178 = 0.04113 -0.01455 -0.00501 -0.03332 AFIX 23 H8A 2 0.269789 0.580487 1.068098 11.00000 -1.20000 H8B 2 0.281954 0.710204 1.029774 11.00000 -1.20000 AFIX 0 C7 1 0.306856 0.598059 0.881025 11.00000 0.05617 0.06588 = 0.04302 0.00205 -0.00013 -0.02788 C13 1 0.397341 0.694427 0.845003 11.00000 0.08670 0.09755 = 0.06839 0.00413 0.00254 -0.05758 AFIX 137 H13A 2 0.468673 0.699613 0.906812 11.00000 -1.50000 H13B 2 0.352499 0.766686 0.840161 11.00000 -1.50000 H13C 2 0.427268 0.677066 0.765578 11.00000 -1.50000 AFIX 0 C10 1 0.201617 0.578103 0.777219 11.00000 0.05139 0.04694 = 0.03030 0.00407 0.00711 -0.01474 AFIX 23 H10A 2 0.238683 0.550214 0.703684 11.00000 -1.20000 H10B 2 0.158908 0.650629 0.756181 11.00000 -1.20000 AFIX 0 C12 1 -0.155572 0.656221 0.857423 11.00000 0.08021 0.05025 = 0.04106 0.00013 0.01199 0.02153 AFIX 137 H12A 2 -0.113907 0.679656 0.785901 11.00000 -1.50000 H12B 2 -0.138647 0.711771 0.922909 11.00000 -1.50000 H12C 2 -0.245854 0.651412 0.835597 11.00000 -1.50000 AFIX 0 F1 5 0.729339 0.587488 0.514645 11.00000 0.10433 0.29126 = 0.19001 -0.02505 -0.02635 -0.03245 F2 5 0.732381 0.585966 0.330770 11.00000 0.08853 0.40276 = 0.19330 0.11410 0.04877 -0.01165 F3 5 0.728589 0.443517 0.437761 11.00000 0.07320 0.25392 = 0.40922 0.00486 -0.02326 0.02080 HKLF 4 REM 01_a.res in P2(1) REM R1 = 0.0436 for 4641 Fo > 4sig(Fo) and 0.0578 for all 5668 data REM 302 parameters refined using 19 restraints END WGHT 0.0735 0.1300 REM Instructions for potential hydrogen bonds EQIV $1 -x, y-1/2, -z+1 HTAB N1 O2_$1 EQIV $2 x-1, y, z HTAB C2 I1_$2 HTAB C15 O2_$1 REM Highest difference peak 0.557, deepest hole -0.788, 1-sigma level 0.123 Q1 1 0.7335 0.4604 0.3173 11.00000 0.05 0.56 Q2 1 0.7225 0.3889 0.3025 11.00000 0.05 0.40 Q3 1 0.2598 0.5141 0.6733 11.00000 0.05 0.37 Q4 1 0.4618 0.6026 1.1045 11.00000 0.05 0.37 Q5 1 0.2660 0.4197 0.6582 11.00000 0.05 0.36 Q6 1 0.7123 0.6716 0.4156 11.00000 0.05 0.36 Q7 1 0.2712 0.3880 0.6562 11.00000 0.05 0.36 Q8 1 0.0075 0.6251 0.6878 11.00000 0.05 0.35 ; _shelx_res_checksum 64491 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -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 I1 I 0.48839(4) 0.42119(8) 0.76371(5) 0.0996(3) Uani 1 1 d . . . . . S1 S 0.10826(12) 0.53642(9) 0.34186(9) 0.0384(3) Uani 1 1 d . . . . . O1 O 0.0751(4) 0.4532(3) 0.2456(3) 0.0517(9) Uani 1 1 d . . . . . N1 N 0.0021(4) 0.3861(3) 0.6257(3) 0.0333(7) Uani 1 1 d . . . . . H1 H -0.0131 0.3163 0.6474 0.040 Uiso 1 1 calc R U . . . N2 N 0.0635(4) 0.5070(3) 0.4761(3) 0.0362(8) Uani 1 1 d . . . . . O2 O 0.0717(4) 0.6540(3) 0.3152(3) 0.0574(10) Uani 1 1 d . . . . . C3A C 0.1046(5) 0.4905(4) 0.8162(3) 0.0332(8) Uani 1 1 d . . . . . C2 C -0.1228(4) 0.4511(4) 0.7951(4) 0.0367(9) Uani 1 1 d . . . . . H2A H -0.2035 0.4637 0.7460 0.044 Uiso 1 1 calc R U . . . H2B H -0.1199 0.3723 0.8257 0.044 Uiso 1 1 calc R U . . . C6 C 0.3754(5) 0.4835(6) 0.9131(5) 0.0601(14) Uani 1 1 d . . . . . H6 H 0.4342 0.4962 0.9876 0.072 Uiso 1 1 calc R U . . . C5 C 0.2850(5) 0.3855(5) 0.9418(5) 0.0521(13) Uani 1 1 d . . . . . H5A H 0.3319 0.3133 0.9473 0.063 Uiso 1 1 calc R U . . . H5B H 0.2527 0.3996 1.0219 0.063 Uiso 1 1 calc R U . . . C4 C 0.1732(5) 0.3746(4) 0.8425(4) 0.0390(10) Uani 1 1 d . . . . . H4A H 0.1129 0.3187 0.8696 0.047 Uiso 1 1 calc R U . . . H4B H 0.2040 0.3461 0.7661 0.047 Uiso 1 1 calc R U . . . C3 C -0.0106(4) 0.4761(3) 0.7188(3) 0.0306(8) Uani 1 1 d . . . . . H3 H -0.0262 0.5499 0.6756 0.037 Uiso 1 1 calc R U . . . C14 C 0.0350(4) 0.4018(4) 0.5114(3) 0.0320(8) Uani 1 1 d . . . . . C16 C 0.2776(5) 0.5362(4) 0.3666(4) 0.0431(10) Uani 1 1 d . . . . . C17 C 0.3453(6) 0.4453(5) 0.3271(6) 0.0633(14) Uani 1 1 d . . . . . H17 H 0.3025 0.3822 0.2899 0.076 Uiso 1 1 calc R U . . . C18 C 0.4766(7) 0.4458(8) 0.3416(8) 0.085(2) Uani 1 1 d . . . . . H18 H 0.5223 0.3843 0.3125 0.102 Uiso 1 1 calc R U . . . C19 C 0.5388(7) 0.5365(8) 0.3986(6) 0.0774(18) Uani 1 1 d . . . . . C22 C 0.6790(9) 0.5334(15) 0.4096(10) 0.120(4) Uani 1 1 d . . . . . C15 C 0.0351(7) 0.2931(4) 0.4347(5) 0.0560(14) Uani 1 1 d . . . . . H15A H 0.0209 0.2277 0.4863 0.084 Uiso 1 1 calc R U . . . H15B H 0.1160 0.2851 0.4010 0.084 Uiso 1 1 calc R U . . . H15C H -0.0315 0.2973 0.3679 0.084 Uiso 1 1 calc R U . . . C20 C 0.4720(8) 0.6287(7) 0.4394(8) 0.087(2) Uani 1 1 d . . . . . H20 H 0.5153 0.6910 0.4776 0.104 Uiso 1 1 calc R U . . . C21 C 0.3404(7) 0.6288(6) 0.4236(7) 0.0720(17) Uani 1 1 d . . . . . H21 H 0.2946 0.6910 0.4513 0.086 Uiso 1 1 calc R U . . . C1 C -0.1047(5) 0.5371(4) 0.9022(4) 0.0391(9) Uani 1 1 d . . . . . C11 C -0.1764(6) 0.5007(5) 1.0133(4) 0.0540(13) Uani 1 1 d . . . . . H11A H -0.2665 0.5016 0.9896 0.081 Uiso 1 1 calc R U . . . H11B H -0.1571 0.5536 1.0810 0.081 Uiso 1 1 calc R U . . . H11C H -0.1506 0.4243 1.0391 0.081 Uiso 1 1 calc R U . . . C9A C 0.0420(4) 0.5345(4) 0.9347(3) 0.0365(9) Uani 1 1 d . . . . . H9A H 0.0589 0.4754 0.9991 0.044 Uiso 1 1 calc R U . . . C9 C 0.1032(6) 0.6462(5) 0.9865(5) 0.0550(14) Uani 1 1 d . . . . . H9B H 0.0793 0.7093 0.9301 0.066 Uiso 1 1 calc R U . . . H9C H 0.0716 0.6635 1.0662 0.066 Uiso 1 1 calc R U . . . C8 C 0.2463(7) 0.6362(6) 1.0028(5) 0.0650(17) Uani 1 1 d . . . . . H8A H 0.2698 0.5805 1.0681 0.078 Uiso 1 1 calc R U . . . H8B H 0.2820 0.7102 1.0298 0.078 Uiso 1 1 calc R U . . . C7 C 0.3069(6) 0.5981(5) 0.8810(5) 0.0553(14) Uani 1 1 d . . . . . C13 C 0.3973(8) 0.6944(7) 0.8450(7) 0.084(2) Uani 1 1 d . . . . . H13A H 0.4687 0.6996 0.9068 0.127 Uiso 1 1 calc R U . . . H13B H 0.3525 0.7667 0.8402 0.127 Uiso 1 1 calc R U . . . H13C H 0.4273 0.6771 0.7656 0.127 Uiso 1 1 calc R U . . . C10 C 0.2016(5) 0.5781(4) 0.7772(4) 0.0427(11) Uani 1 1 d . . . . . H10A H 0.2387 0.5502 0.7037 0.051 Uiso 1 1 calc R U . . . H10B H 0.1589 0.6506 0.7562 0.051 Uiso 1 1 calc R U . . . C12 C -0.1556(7) 0.6562(5) 0.8574(5) 0.0568(14) Uani 1 1 d . . . . . H12A H -0.1139 0.6797 0.7859 0.085 Uiso 1 1 calc R U . . . H12B H -0.1386 0.7118 0.9229 0.085 Uiso 1 1 calc R U . . . H12C H -0.2459 0.6514 0.8356 0.085 Uiso 1 1 calc R U . . . F1 F 0.7293(9) 0.5875(12) 0.5146(10) 0.198(4) Uani 1 1 d . U . . . F2 F 0.7324(8) 0.5860(14) 0.3308(10) 0.226(5) Uani 1 1 d . U . . . F3 F 0.7286(8) 0.4435(13) 0.4378(14) 0.248(5) 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 I1 0.0452(2) 0.1515(6) 0.1045(4) -0.0109(4) 0.0203(2) -0.0040(3) S1 0.0564(7) 0.0363(5) 0.0234(4) 0.0023(4) 0.0084(4) 0.0086(5) O1 0.073(2) 0.058(2) 0.0244(15) -0.0037(13) 0.0045(14) 0.0010(17) N1 0.0436(19) 0.0308(17) 0.0257(16) -0.0018(12) 0.0041(14) -0.0024(13) N2 0.051(2) 0.0348(19) 0.0235(15) -0.0031(13) 0.0072(15) 0.0042(15) O2 0.089(3) 0.0445(18) 0.0412(18) 0.0099(15) 0.0207(18) 0.0240(18) C3A 0.044(2) 0.0350(19) 0.0215(17) 0.0007(15) 0.0056(16) -0.0039(18) C2 0.039(2) 0.044(2) 0.0272(19) 0.0005(16) 0.0069(16) -0.0006(18) C6 0.040(3) 0.092(4) 0.047(3) 0.004(3) -0.003(2) -0.018(3) C5 0.047(3) 0.061(3) 0.047(3) 0.014(2) -0.005(2) -0.003(2) C4 0.039(2) 0.039(2) 0.039(2) 0.0040(17) 0.0040(18) -0.0036(17) C3 0.040(2) 0.0296(19) 0.0224(17) -0.0022(14) 0.0051(15) 0.0008(15) C14 0.0374(19) 0.036(2) 0.0225(17) -0.0046(16) 0.0024(14) -0.0003(17) C16 0.056(3) 0.044(2) 0.031(2) 0.004(2) 0.0149(18) -0.001(2) C17 0.059(3) 0.056(3) 0.076(4) -0.011(3) 0.014(3) 0.010(3) C18 0.064(4) 0.102(6) 0.091(5) -0.012(4) 0.019(3) 0.024(4) C19 0.062(4) 0.103(5) 0.067(4) 0.020(4) 0.009(3) -0.004(4) C22 0.057(5) 0.201(11) 0.101(6) 0.046(8) 0.006(5) 0.024(7) C15 0.092(4) 0.036(2) 0.041(3) -0.010(2) 0.014(3) -0.006(3) C20 0.080(5) 0.086(5) 0.093(5) -0.010(4) 0.006(4) -0.027(4) C21 0.075(5) 0.060(3) 0.082(4) -0.014(3) 0.012(3) -0.014(3) C1 0.052(3) 0.043(2) 0.0238(18) 0.0016(19) 0.0106(16) 0.005(2) C11 0.060(3) 0.071(3) 0.035(2) 0.001(2) 0.021(2) 0.001(3) C9A 0.054(3) 0.0373(19) 0.0190(16) 0.0014(17) 0.0064(16) -0.007(2) C9 0.079(4) 0.050(3) 0.036(2) -0.013(2) 0.006(2) -0.020(3) C8 0.080(5) 0.072(4) 0.041(3) -0.015(3) -0.005(3) -0.033(3) C7 0.056(3) 0.066(3) 0.043(3) 0.002(2) 0.000(2) -0.028(3) C13 0.087(5) 0.098(5) 0.068(4) 0.004(4) 0.003(3) -0.058(4) C10 0.051(3) 0.047(2) 0.030(2) 0.0041(17) 0.0071(19) -0.015(2) C12 0.080(4) 0.050(3) 0.041(3) 0.000(2) 0.012(3) 0.022(3) F1 0.104(5) 0.291(10) 0.190(7) -0.025(7) -0.026(5) -0.032(6) F2 0.089(5) 0.403(12) 0.193(7) 0.114(8) 0.049(5) -0.012(6) F3 0.073(4) 0.254(9) 0.409(12) 0.005(10) -0.023(6) 0.021(7) 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' I I -0.4742 1.8119 '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 O1 S1 N2 116.0(2) . . ? O1 S1 O2 116.6(2) . . ? O1 S1 C16 106.4(2) . . ? N2 S1 C16 103.7(2) . . ? O2 S1 N2 106.72(19) . . ? O2 S1 C16 106.2(3) . . ? C3 N1 H1 117.0 . . ? C14 N1 H1 117.0 . . ? C14 N1 C3 126.1(3) . . ? C14 N2 S1 123.5(3) . . ? C4 C3A C3 111.0(3) . . ? C4 C3A C9A 110.9(3) . . ? C3 C3A C9A 103.1(3) . . ? C10 C3A C4 108.4(4) . . ? C10 C3A C3 113.0(3) . . ? C10 C3A C9A 110.4(3) . . ? H2A C2 H2B 109.0 . . ? C3 C2 H2A 111.1 . . ? C3 C2 H2B 111.1 . . ? C1 C2 H2A 111.1 . . ? C1 C2 H2B 111.1 . . ? C1 C2 C3 103.5(3) . . ? I1 C6 H6 107.7 . . ? C5 C6 I1 106.9(4) . . ? C5 C6 H6 107.7 . . ? C5 C6 C7 113.5(5) . . ? C7 C6 I1 113.0(4) . . ? C7 C6 H6 107.7 . . ? C6 C5 H5A 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C4 C5 C6 112.0(4) . . ? C4 C5 H5A 109.2 . . ? C4 C5 H5B 109.2 . . ? C3A C4 H4A 109.2 . . ? C3A C4 H4B 109.2 . . ? C5 C4 C3A 112.2(4) . . ? C5 C4 H4A 109.2 . . ? C5 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? N1 C3 C3A 115.4(3) . . ? N1 C3 C2 111.0(3) . . ? N1 C3 H3 108.5 . . ? C3A C3 H3 108.5 . . ? C2 C3 C3A 104.7(3) . . ? C2 C3 H3 108.5 . . ? N1 C14 C15 114.2(4) . . ? N2 C14 N1 118.8(3) . . ? N2 C14 C15 127.0(4) . . ? C17 C16 S1 120.0(4) . . ? C17 C16 C21 120.0(6) . . ? C21 C16 S1 120.0(4) . . ? C16 C17 H17 119.7 . . ? C16 C17 C18 120.6(6) . . ? C18 C17 H17 119.7 . . ? C17 C18 H18 120.2 . . ? C19 C18 C17 119.6(7) . . ? C19 C18 H18 120.2 . . ? C18 C19 C22 117.2(9) . . ? C18 C19 C20 120.5(7) . . ? C20 C19 C22 122.2(10) . . ? F1 C22 C19 111.7(10) . . ? F2 C22 C19 116.9(9) . . ? F2 C22 F1 100.4(14) . . ? F3 C22 C19 117.1(12) . . ? F3 C22 F1 93.5(10) . . ? F3 C22 F2 113.2(13) . . ? 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 . . ? C19 C20 H20 120.0 . . ? C19 C20 C21 119.9(7) . . ? C21 C20 H20 120.0 . . ? C16 C21 C20 119.4(7) . . ? C16 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C2 C1 C11 112.1(4) . . ? C2 C1 C9A 102.3(3) . . ? C2 C1 C12 109.3(4) . . ? C11 C1 C9A 111.6(4) . . ? C11 C1 C12 108.0(4) . . ? C12 C1 C9A 113.5(4) . . ? 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 . . ? C3A C9A H9A 106.7 . . ? C1 C9A C3A 107.7(3) . . ? C1 C9A H9A 106.7 . . ? C9 C9A C3A 112.2(4) . . ? C9 C9A C1 116.4(4) . . ? C9 C9A H9A 106.7 . . ? C9A C9 H9B 109.4 . . ? C9A C9 H9C 109.4 . . ? H9B C9 H9C 108.0 . . ? C8 C9 C9A 111.2(5) . . ? C8 C9 H9B 109.4 . . ? C8 C9 H9C 109.4 . . ? C9 C8 H8A 108.8 . . ? C9 C8 H8B 108.8 . . ? C9 C8 C7 113.6(4) . . ? H8A C8 H8B 107.7 . . ? C7 C8 H8A 108.8 . . ? C7 C8 H8B 108.8 . . ? C6 C7 C8 105.8(5) . . ? C6 C7 C13 113.2(6) . . ? C13 C7 C8 108.3(5) . . ? C10 C7 C6 109.4(4) . . ? C10 C7 C8 109.5(5) . . ? C10 C7 C13 110.5(5) . . ? C7 C13 H13A 109.5 . . ? C7 C13 H13B 109.5 . . ? C7 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C3A C10 H10A 109.4 . . ? C3A C10 H10B 109.4 . . ? C7 C10 C3A 111.1(4) . . ? C7 C10 H10A 109.4 . . ? C7 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? 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 . . ? 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 I1 C6 2.208(6) . ? S1 O1 1.436(3) . ? S1 N2 1.599(4) . ? S1 O2 1.437(3) . ? S1 C16 1.779(5) . ? N1 H1 0.8600 . ? N1 C3 1.462(5) . ? N1 C14 1.322(5) . ? N2 C14 1.319(6) . ? C3A C4 1.539(6) . ? C3A C3 1.540(6) . ? C3A C9A 1.574(6) . ? C3A C10 1.525(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C2 C3 1.526(6) . ? C2 C1 1.524(6) . ? C6 H6 0.9800 . ? C6 C5 1.531(8) . ? C6 C7 1.535(10) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 C4 1.523(7) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C3 H3 0.9800 . ? C14 C15 1.507(6) . ? C16 C17 1.360(8) . ? C16 C21 1.377(8) . ? C17 H17 0.9300 . ? C17 C18 1.377(10) . ? C18 H18 0.9300 . ? C18 C19 1.355(12) . ? C19 C22 1.470(12) . ? C19 C20 1.373(12) . ? C22 F1 1.360(16) . ? C22 F2 1.223(14) . ? C22 F3 1.192(16) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C20 H20 0.9300 . ? C20 C21 1.380(12) . ? C21 H21 0.9300 . ? C1 C11 1.532(6) . ? C1 C9A 1.552(7) . ? C1 C12 1.542(7) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C9A H9A 0.9800 . ? C9A C9 1.529(6) . ? C9 H9B 0.9700 . ? C9 H9C 0.9700 . ? C9 C8 1.505(10) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 C7 1.574(9) . ? C7 C13 1.540(8) . ? C7 C10 1.520(7) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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 I1 C6 C5 C4 -75.9(5) . . . . ? I1 C6 C7 C8 -173.2(3) . . . . ? I1 C6 C7 C13 -54.8(5) . . . . ? I1 C6 C7 C10 69.0(5) . . . . ? S1 N2 C14 N1 178.3(3) . . . . ? S1 N2 C14 C15 -1.8(7) . . . . ? S1 C16 C17 C18 177.7(5) . . . . ? S1 C16 C21 C20 -178.4(6) . . . . ? O1 S1 N2 C14 20.9(5) . . . . ? O1 S1 C16 C17 -18.8(5) . . . . ? O1 S1 C16 C21 160.1(4) . . . . ? N2 S1 C16 C17 104.1(4) . . . . ? N2 S1 C16 C21 -77.1(5) . . . . ? O2 S1 N2 C14 152.8(4) . . . . ? O2 S1 C16 C17 -143.6(4) . . . . ? O2 S1 C16 C21 35.2(5) . . . . ? C3A C9A C9 C8 -50.1(5) . . . . ? C2 C1 C9A C3A 22.8(4) . . . . ? C2 C1 C9A C9 149.7(4) . . . . ? C6 C5 C4 C3A -51.4(6) . . . . ? C6 C7 C10 C3A 59.8(6) . . . . ? C5 C6 C7 C8 64.9(6) . . . . ? C5 C6 C7 C13 -176.7(5) . . . . ? C5 C6 C7 C10 -53.0(6) . . . . ? C4 C3A C3 N1 -31.2(5) . . . . ? C4 C3A C3 C2 91.1(4) . . . . ? C4 C3A C9A C1 -116.1(4) . . . . ? C4 C3A C9A C9 114.7(4) . . . . ? C4 C3A C10 C7 -62.0(5) . . . . ? C3 N1 C14 N2 2.3(6) . . . . ? C3 N1 C14 C15 -177.6(4) . . . . ? C3 C3A C4 C5 -178.1(4) . . . . ? C3 C3A C9A C1 2.8(4) . . . . ? C3 C3A C9A C9 -126.4(4) . . . . ? C3 C3A C10 C7 174.5(4) . . . . ? C3 C2 C1 C11 -159.8(4) . . . . ? C3 C2 C1 C9A -40.1(4) . . . . ? C3 C2 C1 C12 80.5(5) . . . . ? C14 N1 C3 C3A -98.8(5) . . . . ? C14 N1 C3 C2 142.4(4) . . . . ? C16 S1 N2 C14 -95.4(4) . . . . ? C16 C17 C18 C19 1.6(11) . . . . ? C17 C16 C21 C20 0.4(10) . . . . ? C17 C18 C19 C22 -178.9(7) . . . . ? C17 C18 C19 C20 -1.4(12) . . . . ? C18 C19 C22 F1 -148.2(11) . . . . ? C18 C19 C22 F2 97.0(16) . . . . ? C18 C19 C22 F3 -42.1(16) . . . . ? C18 C19 C20 C21 0.7(12) . . . . ? C19 C20 C21 C16 -0.2(12) . . . . ? C22 C19 C20 C21 178.1(8) . . . . ? C20 C19 C22 F1 34.3(14) . . . . ? C20 C19 C22 F2 -80.5(17) . . . . ? C20 C19 C22 F3 140.4(14) . . . . ? C21 C16 C17 C18 -1.1(9) . . . . ? C1 C2 C3 N1 168.5(3) . . . . ? C1 C2 C3 C3A 43.3(4) . . . . ? C1 C9A C9 C8 -174.7(4) . . . . ? C11 C1 C9A C3A 142.9(4) . . . . ? C11 C1 C9A C9 -90.3(5) . . . . ? C9A C3A C4 C5 -64.1(5) . . . . ? C9A C3A C3 N1 -150.0(3) . . . . ? C9A C3A C3 C2 -27.7(4) . . . . ? C9A C3A C10 C7 59.6(5) . . . . ? C9A C9 C8 C7 54.3(6) . . . . ? C9 C8 C7 C6 -119.1(5) . . . . ? C9 C8 C7 C13 119.2(6) . . . . ? C9 C8 C7 C10 -1.4(7) . . . . ? C8 C7 C10 C3A -55.7(6) . . . . ? C7 C6 C5 C4 49.4(7) . . . . ? C13 C7 C10 C3A -174.9(6) . . . . ? C10 C3A C4 C5 57.3(5) . . . . ? C10 C3A C3 N1 90.9(4) . . . . ? C10 C3A C3 C2 -146.8(4) . . . . ? C10 C3A C9A C1 123.8(4) . . . . ? C10 C3A C9A C9 -5.5(5) . . . . ? C12 C1 C9A C3A -94.8(4) . . . . ? C12 C1 C9A C9 32.0(5) . . . . ?