#------------------------------------------------------------------------------ #$Date: 2026-03-04 22:02:50 +0000 (Wed, 04 Mar 2026) $ #$Revision: 304785 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064320.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_7064320 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 'C18 H28 Br F3 N2 O2 S' _chemical_formula_sum 'C18 H28 Br F3 N2 O2 S' _chemical_formula_weight 473.39 _chemical_melting_point 444.2 _chemical_name_systematic N-(6-bromo-1,1,7-trimethyldecahydro-3a,7-methanocyclopenta[8]annulen-3-yl)-N'-((trifluoromethyl)sulfonyl)acetimidamide _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _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 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.3387(5) _cell_length_b 8.9043(6) _cell_length_c 32.227(2) _cell_measurement_reflns_used 9756 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 61.18 _cell_measurement_theta_min 2.74 _cell_volume 2105.9(2) _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 0.859 _diffrn_measured_fraction_theta_max 1.001 _diffrn_measurement_device_type 'Bruker D8 VENTURE PHOTON 100 CMOS' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0550 _diffrn_reflns_av_unetI/netI 0.0226 _diffrn_reflns_Laue_measured_fraction_full 0.859 _diffrn_reflns_Laue_measured_fraction_max 1.001 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_number 31942 _diffrn_reflns_point_group_measured_fraction_full 0.850 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 61.292 _diffrn_reflns_theta_min 2.742 _diffrn_source_current 1.0 _diffrn_source_power 0.05 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 3.961 _exptl_absorpt_correction_T_max 0.7520 _exptl_absorpt_correction_T_min 0.4661 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1525 before and 0.0740 after correction. The Ratio of minimum to maximum transmission is 0.6198. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.493 _exptl_crystal_description needle _exptl_crystal_F_000 976 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: chloroform' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.155 _exptl_crystal_size_min 0.095 _refine_diff_density_max 0.284 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.047 _refine_ls_abs_structure_details ; Flack x determined using 1258 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.027(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 248 _refine_ls_number_reflns 3241 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0290 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0344P)^2^+0.9429P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0712 _refine_ls_wR_factor_ref 0.0722 _reflns_Friedel_coverage 0.697 _reflns_Friedel_fraction_full 0.838 _reflns_Friedel_fraction_max 0.996 _reflns_number_gt 3120 _reflns_number_total 3241 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5nj03976b2.cif _cod_data_source_block 3b _cod_database_code 7064320 _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 0.705 _shelx_estimated_absorpt_t_min 0.383 _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.a Ternary CH refined with riding coordinates: C3(H3), C6(H6), C9A(H9A) 2.b Secondary CH2 refined with riding coordinates: C10(H10A,H10B), C5(H5A,H5B), C4(H4A,H4B), C2(H2A,H2B), C9(H9B,H9C), C8(H8A,H8B) 2.c Aromatic/amide H refined with riding coordinates: N1(H1) 2.d Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C11(H11A,H11B,H11C), C12(H12A,H12B, H12C) ; _shelx_res_file ; TITL 1 in P2(1)2(1)2(1) CELL 1.54178 7.3387 8.9043 32.2266 90 90 90 ZERR 4 0.0005 0.0006 0.002 0 0 0 LATT -1 SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5-X,-Y,0.5+Z SFAC C H N O F S Br UNIT 72 112 8 8 12 4 4 L.S. 10 PLAN 6 SIZE 0.095 0.155 0.3 TEMP -273.15 CONF BOND $H MORE -1 HTAB fmap 2 acta REM REM REM WGHT 0.034400 0.942900 FVAR 0.15213 BR1 7 0.490645 -0.339682 0.058844 11.00000 0.09204 0.05377 = 0.05652 -0.00444 -0.01753 -0.00720 S1 6 0.327312 -0.174209 0.221394 11.00000 0.02578 0.04820 = 0.04195 0.00299 0.00235 -0.00130 F1 5 0.415948 -0.425459 0.185476 11.00000 0.07673 0.07671 = 0.21110 -0.06014 0.01914 0.00886 F2 5 0.228892 -0.292806 0.150982 11.00000 0.12858 0.12667 = 0.07326 -0.03033 -0.01754 -0.03667 F3 5 0.139386 -0.412282 0.204266 11.00000 0.07746 0.07684 = 0.14228 -0.02285 0.02629 -0.04064 O1 4 0.170711 -0.080720 0.215762 11.00000 0.02672 0.05906 = 0.09910 -0.00395 -0.00154 0.00242 O2 4 0.353637 -0.234997 0.261502 11.00000 0.04751 0.11904 = 0.04390 0.02298 0.01059 -0.01428 N2 3 0.493733 -0.098172 0.199514 11.00000 0.02446 0.04807 = 0.03758 0.01158 -0.00448 -0.00170 N1 3 0.792726 -0.056318 0.187562 11.00000 0.02382 0.04551 = 0.02853 0.00542 -0.00075 0.00150 AFIX 43 H1 2 0.906454 -0.084438 0.191378 11.00000 -1.20000 AFIX 0 C16 1 0.276438 -0.335427 0.188706 11.00000 0.05039 0.05756 = 0.08275 -0.01302 0.01004 -0.01113 C14 1 0.668125 -0.130466 0.208237 11.00000 0.02942 0.04169 = 0.02832 0.00224 -0.00189 0.00170 C3 1 0.762569 0.068642 0.158723 11.00000 0.02802 0.03875 = 0.02562 0.00150 0.00146 -0.00203 AFIX 13 H3 2 0.653559 0.126751 0.168150 11.00000 -1.20000 AFIX 0 C3A 1 0.737178 0.026805 0.112013 11.00000 0.03165 0.03804 = 0.02202 0.00067 0.00150 -0.00097 C10 1 0.536498 0.010249 0.099254 11.00000 0.03190 0.04581 = 0.02395 -0.00049 -0.00056 0.00360 AFIX 23 H10A 2 0.468395 0.101387 0.107565 11.00000 -1.20000 H10B 2 0.482292 -0.076732 0.113875 11.00000 -1.20000 AFIX 0 C7 1 0.518759 -0.012664 0.051899 11.00000 0.04225 0.05328 = 0.02392 0.00103 -0.00431 0.00489 C13 1 0.318157 -0.018032 0.039669 11.00000 0.04665 0.07908 = 0.04115 -0.00365 -0.01500 0.00835 AFIX 137 H13A 2 0.256220 -0.096241 0.055758 11.00000 -1.50000 H13B 2 0.307821 -0.040768 0.010009 11.00000 -1.50000 H13C 2 0.261499 0.079463 0.045380 11.00000 -1.50000 AFIX 0 C6 1 0.621019 -0.157636 0.039644 11.00000 0.05464 0.05632 = 0.02983 -0.00473 -0.00107 0.00642 AFIX 13 H6 2 0.625878 -0.161465 0.008652 11.00000 -1.20000 AFIX 0 C5 1 0.815584 -0.162130 0.055462 11.00000 0.04995 0.06669 = 0.03979 -0.01699 -0.00298 0.01630 AFIX 23 H5A 2 0.890360 -0.091949 0.038796 11.00000 -1.20000 H5B 2 0.864956 -0.264473 0.051258 11.00000 -1.20000 AFIX 0 C4 1 0.833910 -0.120465 0.101435 11.00000 0.03665 0.04964 = 0.03678 -0.00797 -0.00321 0.00978 AFIX 23 H4A 2 0.781967 -0.202212 0.118571 11.00000 -1.20000 H4B 2 0.964718 -0.111196 0.108496 11.00000 -1.20000 AFIX 0 C9A 1 0.823860 0.165093 0.088925 11.00000 0.04302 0.04968 = 0.02964 0.00395 0.00699 -0.00462 AFIX 13 H9A 2 0.930852 0.126351 0.072967 11.00000 -1.20000 AFIX 0 C1 1 0.899580 0.275132 0.122101 11.00000 0.05353 0.04150 = 0.04033 -0.00170 0.00536 -0.00522 C2 1 0.928452 0.172333 0.159338 11.00000 0.04054 0.04583 = 0.03355 -0.00380 -0.00033 -0.00882 AFIX 23 H2A 2 0.933286 0.230862 0.185434 11.00000 -1.20000 H2B 2 1.042729 0.114186 0.156443 11.00000 -1.20000 AFIX 0 C15 1 0.736296 -0.242952 0.239044 11.00000 0.03641 0.07488 = 0.05641 0.02995 -0.00139 0.00601 AFIX 137 H15A 2 0.709301 -0.344551 0.229098 11.00000 -1.50000 H15B 2 0.675969 -0.226625 0.265796 11.00000 -1.50000 H15C 2 0.868263 -0.231348 0.242413 11.00000 -1.50000 AFIX 0 C11 1 1.079136 0.346217 0.107745 11.00000 0.07821 0.06428 = 0.05974 -0.00115 0.01176 -0.03234 AFIX 137 H11A 2 1.056772 0.408542 0.083205 11.00000 -1.50000 H11B 2 1.166466 0.266850 0.100791 11.00000 -1.50000 H11C 2 1.128932 0.408691 0.130066 11.00000 -1.50000 AFIX 0 C12 1 0.766884 0.400992 0.134332 11.00000 0.08529 0.04884 = 0.06252 -0.00099 0.00488 0.00621 AFIX 137 H12A 2 0.814605 0.454607 0.158564 11.00000 -1.50000 H12B 2 0.647918 0.357442 0.141117 11.00000 -1.50000 H12C 2 0.753472 0.471221 0.111118 11.00000 -1.50000 AFIX 0 C9 1 0.693565 0.235802 0.057379 11.00000 0.07618 0.05527 = 0.04191 0.01632 -0.00043 -0.00720 AFIX 23 H9B 2 0.593225 0.286875 0.072295 11.00000 -1.20000 H9C 2 0.759808 0.312302 0.040967 11.00000 -1.20000 AFIX 0 C8 1 0.614462 0.118629 0.028307 11.00000 0.07055 0.06393 = 0.03157 0.01372 -0.00708 -0.00198 AFIX 23 H8A 2 0.713468 0.077066 0.010886 11.00000 -1.20000 H8B 2 0.525110 0.167435 0.009656 11.00000 -1.20000 AFIX 0 HKLF 4 REM 1 in P2(1)2(1)2(1) REM R1 = 0.0290 for 3120 Fo > 4sig(Fo) and 0.0307 for all 3241 data REM 248 parameters refined using 0 restraints END WGHT 0.0344 0.9429 REM Instructions for potential hydrogen bonds EQIV $1 x+1, y, z HTAB N1 O1_$1 EQIV $2 -x+1, y+1/2, -z+1/2 HTAB C3 O2_$2 HTAB C15 O2 REM Highest difference peak 0.284, deepest hole -0.413, 1-sigma level 0.047 Q1 1 0.3825 -0.2785 0.0673 11.00000 0.05 0.28 Q2 1 0.3309 -0.3505 0.1529 11.00000 0.05 0.20 Q3 1 0.1709 -0.1134 0.1868 11.00000 0.05 0.17 Q4 1 0.2338 -0.2685 0.0597 11.00000 0.05 0.17 Q5 1 0.6337 -0.3074 0.2525 11.00000 0.05 0.16 Q6 1 0.5187 -0.4403 0.2114 11.00000 0.05 0.15 ; _shelx_res_checksum 77704 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' 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 0.49064(8) -0.33968(5) 0.05884(2) 0.06744(18) Uani 1 1 d . . . . . S1 S 0.32731(11) -0.17421(11) 0.22139(3) 0.0386(2) Uani 1 1 d . . . . . F1 F 0.4159(5) -0.4255(4) 0.18548(17) 0.1215(16) Uani 1 1 d . . . . . F2 F 0.2289(6) -0.2928(5) 0.15098(11) 0.1095(13) Uani 1 1 d . . . . . F3 F 0.1394(4) -0.4123(4) 0.20427(13) 0.0989(12) Uani 1 1 d . . . . . O1 O 0.1707(4) -0.0807(3) 0.21576(11) 0.0616(8) Uani 1 1 d . . . . . O2 O 0.3536(4) -0.2350(5) 0.26150(9) 0.0701(10) Uani 1 1 d . . . . . N2 N 0.4937(4) -0.0982(3) 0.19951(9) 0.0367(6) Uani 1 1 d . . . . . N1 N 0.7927(4) -0.0563(3) 0.18756(8) 0.0326(6) Uani 1 1 d . . . . . H1 H 0.9065 -0.0844 0.1914 0.039 Uiso 1 1 calc R U . . . C16 C 0.2764(6) -0.3354(6) 0.18871(16) 0.0636(12) Uani 1 1 d . . . . . C14 C 0.6681(5) -0.1305(4) 0.20824(9) 0.0331(8) Uani 1 1 d . . . . . C3 C 0.7626(4) 0.0686(4) 0.15872(10) 0.0308(7) Uani 1 1 d . . . . . H3 H 0.6536 0.1268 0.1681 0.037 Uiso 1 1 calc R U . . . C3A C 0.7372(5) 0.0268(4) 0.11201(9) 0.0306(7) Uani 1 1 d . . . . . C10 C 0.5365(5) 0.0102(4) 0.09925(9) 0.0339(7) Uani 1 1 d . . . . . H10A H 0.4684 0.1014 0.1076 0.041 Uiso 1 1 calc R U . . . H10B H 0.4823 -0.0767 0.1139 0.041 Uiso 1 1 calc R U . . . C7 C 0.5188(5) -0.0127(4) 0.05190(10) 0.0398(8) Uani 1 1 d . . . . . C13 C 0.3182(6) -0.0180(6) 0.03967(13) 0.0556(11) Uani 1 1 d . . . . . H13A H 0.2562 -0.0962 0.0558 0.083 Uiso 1 1 calc R U . . . H13B H 0.3078 -0.0408 0.0100 0.083 Uiso 1 1 calc R U . . . H13C H 0.2615 0.0795 0.0454 0.083 Uiso 1 1 calc R U . . . C6 C 0.6210(5) -0.1576(5) 0.03964(11) 0.0469(9) Uani 1 1 d . . . . . H6 H 0.6259 -0.1615 0.0087 0.056 Uiso 1 1 calc R U . . . C5 C 0.8156(6) -0.1621(6) 0.05546(11) 0.0521(10) Uani 1 1 d . . . . . H5A H 0.8904 -0.0919 0.0388 0.063 Uiso 1 1 calc R U . . . H5B H 0.8650 -0.2645 0.0513 0.063 Uiso 1 1 calc R U . . . C4 C 0.8339(5) -0.1205(4) 0.10144(11) 0.0410(8) Uani 1 1 d . . . . . H4A H 0.7820 -0.2022 0.1186 0.049 Uiso 1 1 calc R U . . . H4B H 0.9647 -0.1112 0.1085 0.049 Uiso 1 1 calc R U . . . C9A C 0.8239(5) 0.1651(5) 0.08893(10) 0.0408(8) Uani 1 1 d . . . . . H9A H 0.9309 0.1264 0.0730 0.049 Uiso 1 1 calc R U . . . C1 C 0.8996(6) 0.2751(5) 0.12210(12) 0.0451(9) Uani 1 1 d . . . . . C2 C 0.9285(5) 0.1723(5) 0.15934(11) 0.0400(8) Uani 1 1 d . . . . . H2A H 0.9333 0.2309 0.1854 0.048 Uiso 1 1 calc R U . . . H2B H 1.0427 0.1142 0.1564 0.048 Uiso 1 1 calc R U . . . C15 C 0.7363(5) -0.2430(6) 0.23904(14) 0.0559(12) Uani 1 1 d . . . . . H15A H 0.7093 -0.3446 0.2291 0.084 Uiso 1 1 calc R U . . . H15B H 0.6760 -0.2266 0.2658 0.084 Uiso 1 1 calc R U . . . H15C H 0.8683 -0.2313 0.2424 0.084 Uiso 1 1 calc R U . . . C11 C 1.0791(7) 0.3462(6) 0.10775(15) 0.0674(13) Uani 1 1 d . . . . . H11A H 1.0568 0.4085 0.0832 0.101 Uiso 1 1 calc R U . . . H11B H 1.1665 0.2668 0.1008 0.101 Uiso 1 1 calc R U . . . H11C H 1.1289 0.4087 0.1301 0.101 Uiso 1 1 calc R U . . . C12 C 0.7669(8) 0.4010(5) 0.13433(16) 0.0656(13) Uani 1 1 d . . . . . H12A H 0.8146 0.4546 0.1586 0.098 Uiso 1 1 calc R U . . . H12B H 0.6479 0.3574 0.1411 0.098 Uiso 1 1 calc R U . . . H12C H 0.7535 0.4712 0.1111 0.098 Uiso 1 1 calc R U . . . C9 C 0.6936(7) 0.2358(5) 0.05738(13) 0.0578(11) Uani 1 1 d . . . . . H9B H 0.5932 0.2869 0.0723 0.069 Uiso 1 1 calc R U . . . H9C H 0.7598 0.3123 0.0410 0.069 Uiso 1 1 calc R U . . . C8 C 0.6145(7) 0.1186(5) 0.02831(12) 0.0554(12) Uani 1 1 d . . . . . H8A H 0.7135 0.0771 0.0109 0.066 Uiso 1 1 calc R U . . . H8B H 0.5251 0.1674 0.0097 0.066 Uiso 1 1 calc R 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 0.0920(4) 0.0538(3) 0.0565(3) -0.0044(2) -0.0175(3) -0.0072(3) S1 0.0258(4) 0.0482(5) 0.0420(4) 0.0030(4) 0.0024(3) -0.0013(4) F1 0.077(2) 0.077(2) 0.211(5) -0.060(3) 0.019(2) 0.0089(18) F2 0.129(3) 0.127(3) 0.073(2) -0.030(2) -0.0175(19) -0.037(3) F3 0.077(2) 0.077(2) 0.142(3) -0.023(2) 0.026(2) -0.0406(17) O1 0.0267(13) 0.0591(18) 0.099(2) -0.0039(17) -0.0015(16) 0.0024(13) O2 0.0475(16) 0.119(3) 0.0439(15) 0.0230(17) 0.0106(13) -0.0143(18) N2 0.0245(14) 0.0481(16) 0.0376(14) 0.0116(13) -0.0045(13) -0.0017(13) N1 0.0238(14) 0.0455(16) 0.0285(13) 0.0054(13) -0.0008(11) 0.0015(12) C16 0.050(2) 0.058(3) 0.083(3) -0.013(3) 0.010(2) -0.011(2) C14 0.0294(16) 0.042(2) 0.0283(16) 0.0022(14) -0.0019(13) 0.0017(15) C3 0.0280(16) 0.0388(19) 0.0256(15) 0.0015(15) 0.0015(13) -0.0020(14) C3A 0.0316(17) 0.0380(19) 0.0220(15) 0.0007(14) 0.0015(13) -0.0010(14) C10 0.0319(18) 0.0458(19) 0.0239(16) -0.0005(14) -0.0006(14) 0.0036(15) C7 0.042(2) 0.053(2) 0.0239(16) 0.0010(14) -0.0043(16) 0.0049(18) C13 0.047(2) 0.079(3) 0.041(2) -0.004(2) -0.0150(18) 0.008(2) C6 0.055(2) 0.056(2) 0.0298(17) -0.0047(19) -0.0011(15) 0.006(2) C5 0.050(2) 0.067(3) 0.0398(19) -0.017(2) -0.0030(17) 0.016(2) C4 0.0367(18) 0.050(2) 0.0368(18) -0.0080(16) -0.0032(16) 0.0098(16) C9A 0.0430(19) 0.050(2) 0.0296(16) 0.0040(17) 0.0070(14) -0.005(2) C1 0.054(2) 0.042(2) 0.040(2) -0.0017(17) 0.0054(17) -0.0052(18) C2 0.0405(18) 0.046(2) 0.0335(17) -0.0038(17) -0.0003(14) -0.0088(18) C15 0.036(2) 0.075(3) 0.056(2) 0.030(2) -0.0014(18) 0.006(2) C11 0.078(3) 0.064(3) 0.060(3) -0.001(3) 0.012(2) -0.032(3) C12 0.085(4) 0.049(2) 0.063(3) -0.001(2) 0.005(3) 0.006(2) C9 0.076(3) 0.055(2) 0.042(2) 0.016(2) 0.000(2) -0.007(2) C8 0.071(3) 0.064(3) 0.0316(19) 0.0137(18) -0.0071(18) -0.002(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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 108.55(17) . . ? O1 S1 C16 102.8(2) . . ? O2 S1 O1 116.6(2) . . ? O2 S1 N2 118.09(16) . . ? O2 S1 C16 104.8(2) . . ? N2 S1 C16 103.93(18) . . ? C14 N2 S1 123.9(2) . . ? C14 N1 H1 116.6 . . ? C14 N1 C3 126.8(3) . . ? C3 N1 H1 116.6 . . ? F1 C16 S1 111.7(3) . . ? F1 C16 F2 108.1(5) . . ? F1 C16 F3 108.1(5) . . ? F2 C16 S1 111.1(4) . . ? F3 C16 S1 110.3(3) . . ? F3 C16 F2 107.4(4) . . ? N2 C14 C15 127.0(3) . . ? N1 C14 N2 116.8(3) . . ? N1 C14 C15 116.2(3) . . ? N1 C3 H3 108.7 . . ? N1 C3 C3A 116.6(3) . . ? N1 C3 C2 109.3(3) . . ? C3A C3 H3 108.7 . . ? C2 C3 H3 108.7 . . ? C2 C3 C3A 104.6(3) . . ? C3 C3A C9A 102.8(3) . . ? C10 C3A C3 113.3(3) . . ? C10 C3A C9A 109.6(3) . . ? C4 C3A C3 111.3(3) . . ? C4 C3A C10 107.6(3) . . ? C4 C3A C9A 112.2(3) . . ? C3A C10 H10A 109.4 . . ? C3A C10 H10B 109.4 . . ? C3A C10 C7 111.0(3) . . ? H10A C10 H10B 108.0 . . ? C7 C10 H10A 109.4 . . ? C7 C10 H10B 109.4 . . ? C10 C7 C8 110.1(3) . . ? C13 C7 C10 109.9(3) . . ? C13 C7 C6 112.1(3) . . ? C13 C7 C8 109.4(3) . . ? C6 C7 C10 108.8(3) . . ? C6 C7 C8 106.4(3) . . ? 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 . . ? Br1 C6 H6 107.5 . . ? C7 C6 Br1 111.7(3) . . ? C7 C6 H6 107.5 . . ? C5 C6 Br1 109.2(3) . . ? C5 C6 C7 113.2(4) . . ? C5 C6 H6 107.5 . . ? C6 C5 H5A 108.8 . . ? C6 C5 H5B 108.8 . . ? C6 C5 C4 113.6(3) . . ? H5A C5 H5B 107.7 . . ? C4 C5 H5A 108.8 . . ? C4 C5 H5B 108.8 . . ? C3A C4 C5 112.5(3) . . ? C3A C4 H4A 109.1 . . ? C3A C4 H4B 109.1 . . ? C5 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? C3A C9A H9A 106.9 . . ? C1 C9A C3A 108.2(3) . . ? C1 C9A H9A 106.9 . . ? C9 C9A C3A 112.5(3) . . ? C9 C9A H9A 106.9 . . ? C9 C9A C1 114.9(4) . . ? C2 C1 C9A 102.3(3) . . ? C2 C1 C11 111.5(4) . . ? C2 C1 C12 108.9(3) . . ? C11 C1 C9A 111.1(3) . . ? C11 C1 C12 108.7(4) . . ? C12 C1 C9A 114.2(4) . . ? C3 C2 H2A 111.0 . . ? C3 C2 H2B 111.0 . . ? C1 C2 C3 104.0(3) . . ? C1 C2 H2A 111.0 . . ? C1 C2 H2B 111.0 . . ? H2A C2 H2B 109.0 . . ? 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 . . ? 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 . . ? C9A C9 H9B 109.3 . . ? C9A C9 H9C 109.3 . . ? H9B C9 H9C 108.0 . . ? C8 C9 C9A 111.5(4) . . ? C8 C9 H9B 109.3 . . ? C8 C9 H9C 109.3 . . ? C7 C8 H8A 109.0 . . ? C7 C8 H8B 109.0 . . ? C9 C8 C7 112.7(3) . . ? C9 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? 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 1.981(5) . ? S1 O1 1.431(3) . ? S1 O2 1.415(3) . ? S1 N2 1.564(3) . ? S1 C16 1.819(5) . ? F1 C16 1.304(6) . ? F2 C16 1.321(6) . ? F3 C16 1.316(5) . ? N2 C14 1.342(5) . ? N1 H1 0.8800 . ? N1 C14 1.310(4) . ? N1 C3 1.467(4) . ? C14 C15 1.496(5) . ? C3 H3 1.0000 . ? C3 C3A 1.562(4) . ? C3 C2 1.528(5) . ? C3A C10 1.536(5) . ? C3A C4 1.530(5) . ? C3A C9A 1.573(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C10 C7 1.545(4) . ? C7 C13 1.525(6) . ? C7 C6 1.545(6) . ? C7 C8 1.561(6) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C6 H6 1.0000 . ? C6 C5 1.517(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C4 1.533(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C9A H9A 1.0000 . ? C9A C1 1.553(6) . ? C9A C9 1.531(6) . ? C1 C2 1.524(6) . ? C1 C11 1.533(6) . ? C1 C12 1.536(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C9 H9B 0.9900 . ? C9 H9C 0.9900 . ? C9 C8 1.518(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? 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 -77.1(4) . . . . ? S1 N2 C14 N1 -179.4(3) . . . . ? S1 N2 C14 C15 0.9(5) . . . . ? O1 S1 N2 C14 160.2(3) . . . . ? O1 S1 C16 F1 171.5(4) . . . . ? O1 S1 C16 F2 50.7(4) . . . . ? O1 S1 C16 F3 -68.2(4) . . . . ? O2 S1 N2 C14 24.5(4) . . . . ? O2 S1 C16 F1 -66.1(4) . . . . ? O2 S1 C16 F2 173.1(3) . . . . ? O2 S1 C16 F3 54.1(4) . . . . ? N2 S1 C16 F1 58.4(4) . . . . ? N2 S1 C16 F2 -62.4(4) . . . . ? N2 S1 C16 F3 178.7(3) . . . . ? N1 C3 C3A C10 94.5(3) . . . . ? N1 C3 C3A C4 -27.0(4) . . . . ? N1 C3 C3A C9A -147.3(3) . . . . ? N1 C3 C2 C1 168.0(3) . . . . ? C16 S1 N2 C14 -91.0(3) . . . . ? C14 N1 C3 C3A -91.5(4) . . . . ? C14 N1 C3 C2 150.3(3) . . . . ? C3 N1 C14 N2 6.4(5) . . . . ? C3 N1 C14 C15 -173.9(3) . . . . ? C3 C3A C10 C7 173.4(3) . . . . ? C3 C3A C4 C5 -178.4(3) . . . . ? C3 C3A C9A C1 1.9(4) . . . . ? C3 C3A C9A C9 -126.2(3) . . . . ? C3A C3 C2 C1 42.4(4) . . . . ? C3A C10 C7 C13 -176.1(3) . . . . ? C3A C10 C7 C6 60.7(4) . . . . ? C3A C10 C7 C8 -55.6(4) . . . . ? C3A C9A C1 C2 23.2(4) . . . . ? C3A C9A C1 C11 142.3(4) . . . . ? C3A C9A C1 C12 -94.3(4) . . . . ? C3A C9A C9 C8 -51.0(5) . . . . ? C10 C3A C4 C5 56.8(4) . . . . ? C10 C3A C9A C1 122.7(3) . . . . ? C10 C3A C9A C9 -5.4(4) . . . . ? C10 C7 C6 Br1 71.5(3) . . . . ? C10 C7 C6 C5 -52.1(4) . . . . ? C10 C7 C8 C9 -1.9(5) . . . . ? C7 C6 C5 C4 47.9(5) . . . . ? C13 C7 C6 Br1 -50.3(4) . . . . ? C13 C7 C6 C5 -173.9(3) . . . . ? C13 C7 C8 C9 119.0(4) . . . . ? C6 C7 C8 C9 -119.6(4) . . . . ? C6 C5 C4 C3A -50.6(5) . . . . ? C4 C3A C10 C7 -63.1(4) . . . . ? C4 C3A C9A C1 -117.8(3) . . . . ? C4 C3A C9A C9 114.1(4) . . . . ? C9A C3A C10 C7 59.2(4) . . . . ? C9A C3A C4 C5 -63.9(4) . . . . ? C9A C1 C2 C3 -40.0(4) . . . . ? C9A C9 C8 C7 55.1(5) . . . . ? C1 C9A C9 C8 -175.5(3) . . . . ? C2 C3 C3A C10 -144.7(3) . . . . ? C2 C3 C3A C4 93.8(3) . . . . ? C2 C3 C3A C9A -26.5(3) . . . . ? C11 C1 C2 C3 -158.8(3) . . . . ? C12 C1 C2 C3 81.3(4) . . . . ? C9 C9A C1 C2 149.9(3) . . . . ? C9 C9A C1 C11 -91.0(4) . . . . ? C9 C9A C1 C12 32.4(5) . . . . ? C8 C7 C6 Br1 -169.8(2) . . . . ? C8 C7 C6 C5 66.5(4) . . . . ?