#------------------------------------------------------------------------------ #$Date: 2021-09-28 03:39:57 +0300 (Tue, 28 Sep 2021) $ #$Revision: 269335 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158318.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_7158318 loop_ _publ_author_name 'Su, Shixuan' 'Yan, Zhipeng' 'Ye, Xingyuan' 'Wang, Jingyang' 'Li, Yuan' 'He, Guangke' _publ_section_title ; PhI(OAc)2-mediated trifluoromethylthiolation/oxidative cyclization of ynamides ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB01642C _journal_year 2021 _chemical_formula_moiety 'C17 H11 Br F3 N O3 S' _chemical_formula_sum 'C17 H11 Br F3 N O3 S' _chemical_formula_weight 446.24 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2021-08-18 _audit_creation_method ; Olex2 1.5 (compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383) ; _audit_update_record ; 2021-08-19 deposited with the CCDC. 2021-09-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.222(13) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.868(5) _cell_length_b 12.831(4) _cell_length_c 7.106(3) _cell_measurement_reflns_used 4025 _cell_measurement_temperature 193.00 _cell_measurement_theta_max 27.375 _cell_measurement_theta_min 2.683 _cell_volume 1717.6(10) _computing_cell_refinement 'SAINT V8.38A (Bruker, 2018)' _computing_data_reduction 'SAINT V8.38A (Bruker, 2018)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 193.00 _diffrn_measured_fraction_theta_full 0.961 _diffrn_measured_fraction_theta_max 0.951 _diffrn_measurement_device_type 'Bruker D8 VENTURE PHOTON 100' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_unetI/netI 0.0755 _diffrn_reflns_Laue_measured_fraction_full 0.961 _diffrn_reflns_Laue_measured_fraction_max 0.951 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 9748 _diffrn_reflns_point_group_measured_fraction_full 0.961 _diffrn_reflns_point_group_measured_fraction_max 0.951 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.663 _diffrn_reflns_theta_min 1.920 _diffrn_source_current 40.0 _diffrn_source_power 2.0 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.563 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6015 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1433 before and 0.0690 after correction. The Ratio of minimum to maximum transmission is 0.8067. The \l/2 correction factor is Not present. ; _exptl_crystal_density_diffrn 1.726 _exptl_crystal_description block _exptl_crystal_F_000 888 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.995 _refine_diff_density_min -1.464 _refine_diff_density_rms 0.171 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 3813 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.062 _refine_ls_R_factor_all 0.0885 _refine_ls_R_factor_gt 0.0668 _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^)+(0.1596P)^2^+3.4299P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2057 _refine_ls_wR_factor_ref 0.2603 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2896 _reflns_number_total 3813 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01642c2.cif _cod_data_source_block a _cod_original_cell_volume 1717.5(10) _cod_database_code 7158318 _shelx_shelxl_version_number 2018/3 _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 0.784 _shelx_estimated_absorpt_t_min 0.748 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Uiso/Uaniso restraints and constraints C1 \\sim C2: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A 3.a Secondary CH2 refined with riding coordinates: C11(H11A,H11B) 3.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17) ; _shelx_res_file ; TITL a_a.res in P2(1)/c a.res created by SHELXL-2018/3 at 15:20:25 on 18-Aug-2021 REM Old TITL A in P2/c #13 REM SHELXT solution in P2(1)/c: R1 0.206, Rweak 0.020, Alpha 0.048 REM 1.677 for 136 systematic absences, Orientation as input REM Formula found by SHELXT: C17 N O7 Br CELL 0.71073 18.8678 12.8312 7.1056 90 93.222 90 ZERR 4 0.0054 0.004 0.0027 0 0.013 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Br F N O S UNIT 68 44 4 12 4 12 4 SIMU 0.005 0.01 2 C1 C2 L.S. 20 PLAN 5 SIZE 0.1 0.12 0.1 TEMP -80.15 CONF list 4 MORE -1 BOND $H fmap 2 53 acta SIZE 0.1 0.12 0.1 TEMP -80.15 REM REM REM WGHT 0.159600 3.429900 FVAR 0.19390 BR1 3 0.428070 0.145330 0.598752 11.00000 0.05067 0.05154 = 0.04665 0.00590 -0.00509 -0.02280 S1 7 0.674984 0.509749 0.346867 11.00000 0.04813 0.04064 = 0.04355 0.01529 -0.00589 -0.00895 F1 4 0.811484 0.548288 0.349413 11.00000 0.05097 0.05976 = 0.09340 0.00993 0.01370 -0.00911 F2 4 0.742313 0.665301 0.231957 11.00000 0.08458 0.07318 = 0.10080 0.05572 -0.00910 -0.02888 F3 4 0.757301 0.644185 0.529349 11.00000 0.10514 0.05696 = 0.07882 -0.01793 0.01725 -0.03733 O1 6 0.754453 0.346553 0.454132 11.00000 0.03777 0.03846 = 0.04133 -0.01044 0.00913 -0.00140 O2 6 0.697667 0.501232 0.821844 11.00000 0.05406 0.04145 = 0.04375 -0.01005 0.00763 0.00743 O3 6 0.865739 0.306430 0.554488 11.00000 0.05167 0.04414 = 0.07606 -0.01491 0.00076 0.00832 N1 5 0.794544 0.412039 0.731922 11.00000 0.04300 0.02819 = 0.03807 0.00056 -0.00471 -0.00439 C1 1 0.511002 0.226371 0.575814 11.00000 0.04957 0.03056 = 0.02683 0.00393 -0.00720 -0.01344 C2 1 0.574828 0.177184 0.541766 11.00000 0.04457 0.02735 = 0.02998 0.00080 -0.00627 -0.00514 AFIX 43 H2 2 0.577000 0.103487 0.530650 11.00000 -1.20000 AFIX 0 C3 1 0.635032 0.237223 0.524365 11.00000 0.04613 0.02591 = 0.02743 -0.00193 -0.00390 0.00473 AFIX 43 H3 2 0.678989 0.204618 0.502164 11.00000 -1.20000 AFIX 0 C4 1 0.631399 0.345084 0.539265 11.00000 0.03711 0.02440 = 0.02618 0.00095 -0.00090 -0.00439 C5 1 0.567774 0.392572 0.574201 11.00000 0.03384 0.02586 = 0.03571 -0.00048 0.00211 0.00033 AFIX 43 H5 2 0.565363 0.466274 0.584859 11.00000 -1.20000 AFIX 0 C6 1 0.508017 0.333382 0.593538 11.00000 0.03525 0.03494 = 0.03321 0.00256 0.00232 0.00708 AFIX 43 H6 2 0.464463 0.366180 0.619204 11.00000 -1.20000 AFIX 0 C7 1 0.697230 0.409599 0.521043 11.00000 0.03075 0.03247 = 0.03460 0.00084 0.00268 -0.00319 C8 1 0.727634 0.449272 0.711317 11.00000 0.03523 0.02451 = 0.03589 -0.00004 0.00430 0.00107 C9 1 0.811283 0.349447 0.577012 11.00000 0.03362 0.02752 = 0.05079 -0.00055 0.00827 0.00520 C10 1 0.749976 0.595773 0.366959 11.00000 0.06006 0.03520 = 0.04921 0.00974 0.00208 -0.01241 C11 1 0.846276 0.432165 0.889622 11.00000 0.04652 0.03849 = 0.03781 0.00658 -0.00704 -0.00338 AFIX 23 H11A 2 0.872971 0.367391 0.920478 11.00000 -1.20000 H11B 2 0.820782 0.452585 1.001938 11.00000 -1.20000 AFIX 0 C12 1 0.897803 0.517381 0.843837 11.00000 0.04247 0.03761 = 0.03563 -0.00041 -0.01169 -0.00593 C13 1 0.882116 0.620903 0.877019 11.00000 0.06654 0.03622 = 0.05963 -0.00819 0.00240 -0.00609 AFIX 43 H13 2 0.838583 0.638581 0.929981 11.00000 -1.20000 AFIX 0 C14 1 0.929158 0.698934 0.833882 11.00000 0.09116 0.03913 = 0.07646 -0.00810 -0.00047 -0.01922 AFIX 43 H14 2 0.918025 0.769933 0.856021 11.00000 -1.20000 AFIX 0 C15 1 0.992223 0.672351 0.758558 11.00000 0.07717 0.05092 = 0.06057 0.00828 -0.01574 -0.02976 AFIX 43 H15 2 1.025237 0.725035 0.729378 11.00000 -1.20000 AFIX 0 C16 1 1.007019 0.572137 0.726419 11.00000 0.04379 0.07456 = 0.06575 0.00304 -0.00054 -0.00503 AFIX 43 H16 2 1.050529 0.554930 0.672882 11.00000 -1.20000 AFIX 0 C17 1 0.961855 0.494534 0.767896 11.00000 0.04541 0.04564 = 0.06642 0.00021 -0.00573 -0.00195 AFIX 43 H17 2 0.974226 0.424108 0.744724 11.00000 -1.20000 AFIX 0 HKLF 4 REM a_a.res in P2(1)/c REM wR2 = 0.2603, GooF = S = 1.062, Restrained GooF = 1.062 for all data REM R1 = 0.0668 for 2896 Fo > 4sig(Fo) and 0.0885 for all 3813 data REM 235 parameters refined using 6 restraints END WGHT 0.1587 2.4019 REM Highest difference peak 0.995, deepest hole -1.464, 1-sigma level 0.171 Q1 1 0.6735 0.5074 0.6881 11.00000 0.05 1.00 Q2 1 0.4452 0.1581 0.4669 11.00000 0.05 0.98 Q3 1 0.4015 0.1556 0.7252 11.00000 0.05 0.84 Q4 1 0.3960 0.1786 0.5181 11.00000 0.05 0.84 Q5 1 0.7286 0.5609 0.9540 11.00000 0.05 0.69 ; _shelx_res_checksum 18009 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, 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 0.42807(4) 0.14533(5) 0.59875(9) 0.0499(3) Uani 1 1 d . . . . . S1 S 0.67498(9) 0.50975(12) 0.3469(2) 0.0444(4) Uani 1 1 d . . . . . F1 F 0.8115(2) 0.5483(4) 0.3494(8) 0.0677(13) Uani 1 1 d . . . . . F2 F 0.7423(3) 0.6653(4) 0.2320(9) 0.0867(19) Uani 1 1 d . . . . . F3 F 0.7573(3) 0.6442(4) 0.5293(8) 0.0799(17) Uani 1 1 d . . . . . O1 O 0.7545(2) 0.3466(3) 0.4541(6) 0.0389(9) Uani 1 1 d . . . . . O2 O 0.6977(3) 0.5012(3) 0.8218(6) 0.0462(10) Uani 1 1 d . . . . . O3 O 0.8657(3) 0.3064(4) 0.5545(8) 0.0574(13) Uani 1 1 d . . . . . N1 N 0.7945(3) 0.4120(4) 0.7319(7) 0.0367(11) Uani 1 1 d . . . . . C1 C 0.5110(3) 0.2264(4) 0.5758(8) 0.0360(11) Uani 1 1 d . U . . . C2 C 0.5748(3) 0.1772(4) 0.5418(8) 0.0343(11) Uani 1 1 d . U . . . H2 H 0.577000 0.103487 0.530650 0.041 Uiso 1 1 calc R U . . . C3 C 0.6350(3) 0.2372(4) 0.5244(7) 0.0334(12) Uani 1 1 d . . . . . H3 H 0.678989 0.204618 0.502164 0.040 Uiso 1 1 calc R U . . . C4 C 0.6314(3) 0.3451(4) 0.5393(7) 0.0293(11) Uani 1 1 d . . . . . C5 C 0.5678(3) 0.3926(4) 0.5742(8) 0.0318(11) Uani 1 1 d . . . . . H5 H 0.565363 0.466274 0.584859 0.038 Uiso 1 1 calc R U . . . C6 C 0.5080(3) 0.3334(4) 0.5935(8) 0.0345(11) Uani 1 1 d . . . . . H6 H 0.464463 0.366180 0.619204 0.041 Uiso 1 1 calc R U . . . C7 C 0.6972(3) 0.4096(4) 0.5210(8) 0.0326(11) Uani 1 1 d . . . . . C8 C 0.7276(3) 0.4493(4) 0.7113(8) 0.0318(11) Uani 1 1 d . . . . . C9 C 0.8113(3) 0.3494(4) 0.5770(9) 0.0371(13) Uani 1 1 d . . . . . C10 C 0.7500(4) 0.5958(5) 0.3670(10) 0.0482(16) Uani 1 1 d . . . . . C11 C 0.8463(3) 0.4322(5) 0.8896(9) 0.0413(13) Uani 1 1 d . . . . . H11A H 0.872971 0.367391 0.920478 0.050 Uiso 1 1 calc R U . . . H11B H 0.820782 0.452585 1.001938 0.050 Uiso 1 1 calc R U . . . C12 C 0.8978(3) 0.5174(5) 0.8438(8) 0.0391(13) Uani 1 1 d . . . . . C13 C 0.8821(4) 0.6209(5) 0.8770(11) 0.0542(17) Uani 1 1 d . . . . . H13 H 0.838583 0.638581 0.929981 0.065 Uiso 1 1 calc R U . . . C14 C 0.9292(5) 0.6989(6) 0.8339(13) 0.069(2) Uani 1 1 d . . . . . H14 H 0.918025 0.769933 0.856021 0.083 Uiso 1 1 calc R U . . . C15 C 0.9922(5) 0.6724(6) 0.7586(12) 0.064(2) Uani 1 1 d . . . . . H15 H 1.025237 0.725035 0.729378 0.076 Uiso 1 1 calc R U . . . C16 C 1.0070(4) 0.5721(7) 0.7264(12) 0.061(2) Uani 1 1 d . . . . . H16 H 1.050529 0.554930 0.672882 0.074 Uiso 1 1 calc R U . . . C17 C 0.9619(4) 0.4945(6) 0.7679(11) 0.0528(17) Uani 1 1 d . . . . . H17 H 0.974226 0.424108 0.744724 0.063 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 0.0507(5) 0.0515(5) 0.0467(4) 0.0059(3) -0.0051(3) -0.0228(3) S1 0.0481(9) 0.0406(8) 0.0435(8) 0.0153(6) -0.0059(7) -0.0090(6) F1 0.051(2) 0.060(3) 0.093(4) 0.010(2) 0.014(2) -0.009(2) F2 0.085(4) 0.073(3) 0.101(4) 0.056(3) -0.009(3) -0.029(3) F3 0.105(4) 0.057(3) 0.079(3) -0.018(2) 0.017(3) -0.037(3) O1 0.038(2) 0.038(2) 0.041(2) -0.0104(17) 0.0091(18) -0.0014(16) O2 0.054(3) 0.041(2) 0.044(2) -0.0100(19) 0.008(2) 0.0074(19) O3 0.052(3) 0.044(3) 0.076(4) -0.015(2) 0.001(3) 0.008(2) N1 0.043(3) 0.028(2) 0.038(2) 0.0006(18) -0.005(2) -0.0044(18) C1 0.050(3) 0.031(2) 0.027(2) 0.0039(19) -0.007(2) -0.013(2) C2 0.045(3) 0.027(2) 0.030(2) 0.0008(18) -0.006(2) -0.005(2) C3 0.046(3) 0.026(2) 0.027(2) -0.0019(19) -0.004(2) 0.005(2) C4 0.037(3) 0.024(2) 0.026(2) 0.0009(18) -0.001(2) -0.0044(19) C5 0.034(3) 0.026(2) 0.036(3) 0.000(2) 0.002(2) 0.000(2) C6 0.035(3) 0.035(3) 0.033(3) 0.003(2) 0.002(2) 0.007(2) C7 0.031(2) 0.032(3) 0.035(3) 0.001(2) 0.003(2) -0.003(2) C8 0.035(3) 0.025(2) 0.036(3) 0.0000(19) 0.004(2) 0.0011(19) C9 0.034(3) 0.028(3) 0.051(3) -0.001(2) 0.008(3) 0.005(2) C10 0.060(4) 0.035(3) 0.049(4) 0.010(3) 0.002(3) -0.012(3) C11 0.047(3) 0.038(3) 0.038(3) 0.007(2) -0.007(3) -0.003(2) C12 0.042(3) 0.038(3) 0.036(3) 0.000(2) -0.012(2) -0.006(2) C13 0.067(5) 0.036(3) 0.060(4) -0.008(3) 0.002(4) -0.006(3) C14 0.091(6) 0.039(4) 0.076(6) -0.008(4) 0.000(5) -0.019(4) C15 0.077(5) 0.051(4) 0.061(5) 0.008(3) -0.016(4) -0.030(4) C16 0.044(4) 0.075(5) 0.066(5) 0.003(4) -0.001(3) -0.005(3) C17 0.045(4) 0.046(4) 0.066(4) 0.000(3) -0.006(3) -0.002(3) 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' Br Br -0.2901 2.4595 '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' 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' S S 0.1246 0.1234 '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 C10 S1 C7 103.3(3) . . ? C9 O1 C7 110.7(4) . . ? C8 N1 C9 111.4(5) . . ? C8 N1 C11 126.8(5) . . ? C9 N1 C11 121.8(5) . . ? C2 C1 Br1 119.5(4) . . ? C6 C1 Br1 120.0(5) . . ? C6 C1 C2 120.4(5) . . ? C1 C2 H2 120.5 . . ? C3 C2 C1 119.0(5) . . ? C3 C2 H2 120.5 . . ? C2 C3 H3 119.9 . . ? C2 C3 C4 120.2(5) . . ? C4 C3 H3 119.9 . . ? C3 C4 C7 119.8(5) . . ? C5 C4 C3 120.0(5) . . ? C5 C4 C7 120.2(5) . . ? C4 C5 H5 120.0 . . ? C6 C5 C4 120.1(5) . . ? C6 C5 H5 120.0 . . ? C1 C6 H6 119.9 . . ? C5 C6 C1 120.2(5) . . ? C5 C6 H6 119.9 . . ? O1 C7 S1 108.6(4) . . ? O1 C7 C4 110.8(4) . . ? O1 C7 C8 103.1(4) . . ? C4 C7 S1 106.7(4) . . ? C4 C7 C8 112.2(5) . . ? C8 C7 S1 115.4(4) . . ? O2 C8 N1 126.8(5) . . ? O2 C8 C7 126.8(5) . . ? N1 C8 C7 106.3(5) . . ? O1 C9 N1 108.5(5) . . ? O3 C9 O1 124.4(6) . . ? O3 C9 N1 127.1(6) . . ? F1 C10 S1 113.7(5) . . ? F2 C10 S1 107.8(5) . . ? F2 C10 F1 107.8(6) . . ? F3 C10 S1 113.9(5) . . ? F3 C10 F1 104.6(6) . . ? F3 C10 F2 108.9(6) . . ? N1 C11 H11A 109.3 . . ? N1 C11 H11B 109.3 . . ? N1 C11 C12 111.8(5) . . ? H11A C11 H11B 107.9 . . ? C12 C11 H11A 109.3 . . ? C12 C11 H11B 109.3 . . ? C13 C12 C11 120.8(7) . . ? C17 C12 C11 121.2(6) . . ? C17 C12 C13 118.0(6) . . ? C12 C13 H13 119.6 . . ? C14 C13 C12 120.7(8) . . ? C14 C13 H13 119.6 . . ? C13 C14 H14 120.4 . . ? C15 C14 C13 119.1(8) . . ? C15 C14 H14 120.4 . . ? C14 C15 H15 120.1 . . ? C16 C15 C14 119.9(8) . . ? C16 C15 H15 120.1 . . ? C15 C16 H16 119.0 . . ? C15 C16 C17 122.0(9) . . ? C17 C16 H16 119.0 . . ? C12 C17 H17 119.9 . . ? C16 C17 C12 120.3(7) . . ? C16 C17 H17 119.9 . . ? 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 C1 1.893(6) . ? S1 C7 1.817(6) . ? S1 C10 1.794(7) . ? F1 C10 1.323(9) . ? F2 C10 1.312(8) . ? F3 C10 1.311(9) . ? O1 C7 1.450(7) . ? O1 C9 1.345(8) . ? O2 C8 1.196(7) . ? O3 C9 1.185(8) . ? N1 C8 1.350(7) . ? N1 C9 1.413(8) . ? N1 C11 1.467(7) . ? C1 C2 1.393(9) . ? C1 C6 1.380(8) . ? C2 H2 0.9500 . ? C2 C3 1.384(8) . ? C3 H3 0.9500 . ? C3 C4 1.390(7) . ? C4 C5 1.381(8) . ? C4 C7 1.504(7) . ? C5 H5 0.9500 . ? C5 C6 1.373(8) . ? C6 H6 0.9500 . ? C7 C8 1.526(7) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C11 C12 1.511(9) . ? C12 C13 1.384(9) . ? C12 C17 1.382(11) . ? C13 H13 0.9500 . ? C13 C14 1.384(11) . ? C14 H14 0.9500 . ? C14 C15 1.375(14) . ? C15 H15 0.9500 . ? C15 C16 1.338(13) . ? C16 H16 0.9500 . ? C16 C17 1.354(11) . ? C17 H17 0.9500 . ? 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 C1 C2 C3 179.7(4) . . . . ? Br1 C1 C6 C5 -179.0(4) . . . . ? S1 C7 C8 O2 65.2(7) . . . . ? S1 C7 C8 N1 -116.2(4) . . . . ? O1 C7 C8 O2 -176.6(6) . . . . ? O1 C7 C8 N1 2.0(5) . . . . ? N1 C11 C12 C13 87.8(8) . . . . ? N1 C11 C12 C17 -92.2(7) . . . . ? C1 C2 C3 C4 -0.5(8) . . . . ? C2 C1 C6 C5 1.2(8) . . . . ? C2 C3 C4 C5 0.9(8) . . . . ? C2 C3 C4 C7 179.7(5) . . . . ? C3 C4 C5 C6 -0.2(8) . . . . ? C3 C4 C7 S1 128.7(5) . . . . ? C3 C4 C7 O1 10.7(7) . . . . ? C3 C4 C7 C8 -104.0(6) . . . . ? C4 C5 C6 C1 -0.8(8) . . . . ? C4 C7 C8 O2 -57.3(8) . . . . ? C4 C7 C8 N1 121.3(5) . . . . ? C5 C4 C7 S1 -52.5(6) . . . . ? C5 C4 C7 O1 -170.5(5) . . . . ? C5 C4 C7 C8 74.8(6) . . . . ? C6 C1 C2 C3 -0.6(8) . . . . ? C7 S1 C10 F1 54.0(6) . . . . ? C7 S1 C10 F2 173.4(5) . . . . ? C7 S1 C10 F3 -65.7(6) . . . . ? C7 O1 C9 O3 -178.4(6) . . . . ? C7 O1 C9 N1 1.2(6) . . . . ? C7 C4 C5 C6 -179.0(5) . . . . ? C8 N1 C9 O1 0.3(7) . . . . ? C8 N1 C9 O3 179.8(6) . . . . ? C8 N1 C11 C12 -98.3(7) . . . . ? C9 O1 C7 S1 120.9(4) . . . . ? C9 O1 C7 C4 -122.2(5) . . . . ? C9 O1 C7 C8 -2.0(6) . . . . ? C9 N1 C8 O2 177.2(6) . . . . ? C9 N1 C8 C7 -1.5(6) . . . . ? C9 N1 C11 C12 80.7(7) . . . . ? C10 S1 C7 O1 -70.9(4) . . . . ? C10 S1 C7 C4 169.7(4) . . . . ? C10 S1 C7 C8 44.3(5) . . . . ? C11 N1 C8 O2 -3.7(10) . . . . ? C11 N1 C8 C7 177.7(5) . . . . ? C11 N1 C9 O1 -178.9(5) . . . . ? C11 N1 C9 O3 0.6(10) . . . . ? C11 C12 C13 C14 -179.6(6) . . . . ? C11 C12 C17 C16 179.4(7) . . . . ? C12 C13 C14 C15 -0.5(12) . . . . ? C13 C12 C17 C16 -0.6(10) . . . . ? C13 C14 C15 C16 0.6(13) . . . . ? C14 C15 C16 C17 -0.8(13) . . . . ? C15 C16 C17 C12 0.8(12) . . . . ? C17 C12 C13 C14 0.5(11) . . . . ?