#------------------------------------------------------------------------------ #$Date: 2021-11-26 00:59:21 +0200 (Fri, 26 Nov 2021) $ #$Revision: 270880 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/93/7129317.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_7129317 loop_ _publ_author_name 'Shi, Hong-Song' 'Li, Shuo-Han' 'Zhang, Fa-Guang' 'Ma, Jun-An' _publ_section_title ; Catalytic regioselective construction of phenylthio- and phenoxyldifluoroalkyl tetrazoles from difluorodiazoketones ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/D1CC05890H _journal_year 2021 _chemical_formula_moiety 'C15 H10 Br F3 N4 S' _chemical_formula_sum 'C15 H10 Br F3 N4 S' _chemical_formula_weight 415.24 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2021-05-16 _audit_creation_method ; Olex2 1.3 (compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032) ; _audit_update_record ; 2021-10-17 deposited with the CCDC. 2021-11-24 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.312(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.1584(16) _cell_length_b 4.7541(7) _cell_length_c 34.462(5) _cell_measurement_reflns_used 4629 _cell_measurement_temperature 296.15 _cell_measurement_theta_max 29.41 _cell_measurement_theta_min 2.38 _cell_volume 1654.2(4) _computing_cell_refinement 'SAINT V8.38A (Bruker, 2018)' _computing_data_reduction 'SAINT V8.38A (Bruker, 2018)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 296.15 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0776 _diffrn_reflns_av_unetI/netI 0.0366 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_number 30213 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.025 _diffrn_reflns_theta_max 25.025 _diffrn_reflns_theta_min 2.039 _diffrn_source_current 1.4 _diffrn_source_power 0.07 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 2.646 _exptl_absorpt_correction_T_max 0.7459 _exptl_absorpt_correction_T_min 0.5765 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0836 before and 0.0537 after correction. The Ratio of minimum to maximum transmission is 0.7729. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.667 _exptl_crystal_description block _exptl_crystal_F_000 824 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.144 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.038 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 217 _refine_ls_number_reflns 2932 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.003 _refine_ls_R_factor_all 0.0762 _refine_ls_R_factor_gt 0.0338 _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^)+(0.0296P)^2^+0.3289P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.0783 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1762 _reflns_number_total 2932 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1cc05890h2.cif _cod_data_source_block shs-2 _cod_database_code 7129317 _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 0.760 _shelx_estimated_absorpt_t_min 0.485 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Ternary CH refined with riding coordinates: C7(H7) 2.b Aromatic/amide H refined with riding coordinates: C11(H11), C14(H14), C2(H2), C15(H15), C12(H12), C3(H3), C4(H4), C6(H6), C5(H5) ; _shelx_res_file ; TITL shs-2_a.res in P2(1)/n shs-2.res created by SHELXL-2018/3 at 16:39:13 on 16-May-2021 REM Old TITL SHS-2 in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.363, Rweak 0.076, Alpha 0.048 REM 0.449 for 428 systematic absences, Orientation as input REM Formula found by SHELXT: C17 N2 O3 S2 CELL 0.71073 10.1584 4.7541 34.4617 90 96.312 90 ZERR 4 0.0016 0.0007 0.0054 0 0.007 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Br F N S UNIT 60 40 4 12 16 4 L.S. 4 0 0 PLAN 5 SIZE 0.32 0.12 0.11 TEMP 23 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta SHEL 999 0.84 REM REM REM WGHT 0.029600 0.328900 FVAR 0.47468 BR1 3 0.855341 1.374544 0.427115 11.00000 0.13156 0.11549 = 0.06789 0.02860 0.01135 -0.00620 S1 6 0.656350 0.595256 0.688543 11.00000 0.09858 0.06170 = 0.06859 -0.00901 0.02581 -0.00518 F2 4 0.935768 0.603782 0.669654 11.00000 0.07886 0.06830 = 0.08739 0.00121 -0.01400 -0.02168 F3 4 0.938825 0.218114 0.638101 11.00000 0.06387 0.08764 = 0.08503 -0.01025 0.00073 0.00968 F1 4 0.906274 0.212552 0.698260 11.00000 0.10420 0.08402 = 0.07459 0.02193 -0.01713 -0.00210 N2 5 0.689933 0.685382 0.560627 11.00000 0.04657 0.05732 = 0.05168 -0.00359 -0.00282 -0.00344 N1 5 0.759582 0.672096 0.595676 11.00000 0.05636 0.05414 = 0.04842 0.00144 -0.00616 -0.00829 N4 5 0.594449 0.364051 0.589269 11.00000 0.05851 0.08229 = 0.06477 -0.00196 0.00040 -0.02264 N3 5 0.590847 0.503154 0.556285 11.00000 0.05417 0.08869 = 0.06669 -0.00338 -0.00610 -0.02277 C9 1 0.696541 0.471312 0.612568 11.00000 0.04547 0.04993 = 0.04936 -0.00583 0.00532 -0.00361 C10 1 0.724884 0.860851 0.529785 11.00000 0.05085 0.05168 = 0.04811 -0.00196 -0.00008 0.00195 C7 1 0.730737 0.372571 0.653407 11.00000 0.05713 0.04754 = 0.05479 -0.00270 0.00541 -0.00782 AFIX 13 H7 2 0.693892 0.183135 0.655246 11.00000 -1.20000 AFIX 0 C8 1 0.877326 0.352763 0.664945 11.00000 0.07672 0.05420 = 0.05808 0.00064 0.00046 -0.00600 C11 1 0.830965 1.037802 0.536465 11.00000 0.07318 0.06642 = 0.04676 -0.00308 -0.00374 -0.01854 AFIX 43 H11 2 0.877761 1.051582 0.561148 11.00000 -1.20000 AFIX 0 C13 1 0.797705 1.175645 0.469601 11.00000 0.07796 0.06312 = 0.05559 0.00898 0.00546 0.00781 C14 1 0.690972 1.002142 0.463365 11.00000 0.07428 0.08785 = 0.05199 0.00523 -0.00999 0.00665 AFIX 43 H14 2 0.643554 0.991437 0.438740 11.00000 -1.20000 AFIX 0 C2 1 0.503537 0.233181 0.725071 11.00000 0.07663 0.07899 = 0.05878 0.00835 0.00962 0.00696 AFIX 43 H2 2 0.575974 0.219530 0.743981 11.00000 -1.20000 AFIX 0 C1 1 0.510416 0.402351 0.693228 11.00000 0.06816 0.06670 = 0.05280 0.00197 0.01346 0.01089 C15 1 0.653381 0.842706 0.493544 11.00000 0.06148 0.07868 = 0.06348 0.00100 -0.01027 -0.00954 AFIX 43 H15 2 0.580437 0.723863 0.489525 11.00000 -1.20000 AFIX 0 C12 1 0.866646 1.193941 0.506041 11.00000 0.08874 0.08226 = 0.05992 0.00412 -0.00086 -0.02603 AFIX 43 H12 2 0.938883 1.314672 0.510096 11.00000 -1.20000 AFIX 0 C3 1 0.389511 0.082287 0.729320 11.00000 0.09162 0.09848 = 0.08625 0.02390 0.02714 0.00475 AFIX 43 H3 2 0.385578 -0.032246 0.751040 11.00000 -1.20000 AFIX 0 C4 1 0.283770 0.101113 0.701935 11.00000 0.07043 0.12962 = 0.10333 -0.00016 0.03164 -0.00323 AFIX 43 H4 2 0.207199 -0.000996 0.704607 11.00000 -1.20000 AFIX 0 C6 1 0.402622 0.422463 0.666056 11.00000 0.07249 0.15223 = 0.07900 0.04268 0.01341 0.01516 AFIX 43 H6 2 0.405434 0.539434 0.644533 11.00000 -1.20000 AFIX 0 C5 1 0.290604 0.271972 0.670250 11.00000 0.06904 0.20106 = 0.08741 0.03330 0.00238 0.01084 AFIX 43 H5 2 0.218107 0.285699 0.651362 11.00000 -1.20000 AFIX 0 HKLF 4 REM shs-2_a.res in P2(1)/n REM wR2 = 0.0783, GooF = S = 1.003, Restrained GooF = 1.003 for all data REM R1 = 0.0338 for 1762 Fo > 4sig(Fo) and 0.0762 for all 2932 data REM 217 parameters refined using 0 restraints END WGHT 0.0283 0.3574 REM Highest difference peak 0.144, deepest hole -0.276, 1-sigma level 0.038 Q1 1 0.5959 0.7858 0.6598 11.00000 0.05 0.14 Q2 1 0.5668 0.6264 0.6727 11.00000 0.05 0.14 Q3 1 0.6579 0.1631 0.7416 11.00000 0.05 0.14 Q4 1 0.5782 0.6550 0.6650 11.00000 0.05 0.14 Q5 1 0.8432 1.2405 0.3980 11.00000 0.05 0.14 ; _shelx_res_checksum 50045 _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+1/2' '-x, -y, -z' 'x-1/2, -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 0.85534(4) 1.37454(9) 0.42711(2) 0.1050(2) Uani 1 1 d . . . . . S1 S 0.65635(9) 0.59526(16) 0.68854(2) 0.0751(3) Uani 1 1 d . . . . . F2 F 0.93577(16) 0.6038(3) 0.66965(5) 0.0799(5) Uani 1 1 d . . . . . F3 F 0.93883(16) 0.2181(4) 0.63810(5) 0.0794(5) Uani 1 1 d . . . . . F1 F 0.90627(19) 0.2126(4) 0.69826(5) 0.0896(6) Uani 1 1 d . . . . . N2 N 0.6899(2) 0.6854(5) 0.56063(7) 0.0525(6) Uani 1 1 d . . . . . N1 N 0.7596(2) 0.6721(4) 0.59568(6) 0.0539(6) Uani 1 1 d . . . . . N4 N 0.5944(2) 0.3641(5) 0.58927(8) 0.0690(7) Uani 1 1 d . . . . . N3 N 0.5908(2) 0.5032(6) 0.55629(8) 0.0708(7) Uani 1 1 d . . . . . C9 C 0.6965(3) 0.4713(6) 0.61257(8) 0.0482(7) Uani 1 1 d . . . . . C10 C 0.7249(3) 0.8609(6) 0.52979(8) 0.0506(7) Uani 1 1 d . . . . . C7 C 0.7307(3) 0.3726(5) 0.65341(8) 0.0532(7) Uani 1 1 d . . . . . H7 H 0.693892 0.183135 0.655246 0.064 Uiso 1 1 calc R U . . . C8 C 0.8773(3) 0.3528(6) 0.66494(9) 0.0635(8) Uani 1 1 d . . . . . C11 C 0.8310(3) 1.0378(6) 0.53647(8) 0.0629(8) Uani 1 1 d . . . . . H11 H 0.877761 1.051582 0.561148 0.075 Uiso 1 1 calc R U . . . C13 C 0.7977(3) 1.1756(6) 0.46960(9) 0.0657(8) Uani 1 1 d . . . . . C14 C 0.6910(3) 1.0021(7) 0.46336(9) 0.0726(9) Uani 1 1 d . . . . . H14 H 0.643554 0.991437 0.438740 0.087 Uiso 1 1 calc R U . . . C2 C 0.5035(3) 0.2332(7) 0.72507(9) 0.0713(9) Uani 1 1 d . . . . . H2 H 0.575974 0.219530 0.743981 0.086 Uiso 1 1 calc R U . . . C1 C 0.5104(3) 0.4024(6) 0.69323(9) 0.0620(8) Uani 1 1 d . . . . . C15 C 0.6534(3) 0.8427(6) 0.49354(9) 0.0692(8) Uani 1 1 d . . . . . H15 H 0.580437 0.723863 0.489525 0.083 Uiso 1 1 calc R U . . . C12 C 0.8666(3) 1.1939(7) 0.50604(9) 0.0776(9) Uani 1 1 d . . . . . H12 H 0.938883 1.314672 0.510096 0.093 Uiso 1 1 calc R U . . . C3 C 0.3895(4) 0.0823(7) 0.72932(11) 0.0908(11) Uani 1 1 d . . . . . H3 H 0.385578 -0.032246 0.751040 0.109 Uiso 1 1 calc R U . . . C4 C 0.2838(4) 0.1011(9) 0.70194(13) 0.0995(12) Uani 1 1 d . . . . . H4 H 0.207199 -0.000996 0.704607 0.119 Uiso 1 1 calc R U . . . C6 C 0.4026(4) 0.4225(9) 0.66606(11) 0.1009(13) Uani 1 1 d . . . . . H6 H 0.405434 0.539434 0.644533 0.121 Uiso 1 1 calc R U . . . C5 C 0.2906(4) 0.2720(11) 0.67025(12) 0.1196(15) Uani 1 1 d . . . . . H5 H 0.218107 0.285699 0.651362 0.144 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 0.1316(4) 0.1155(4) 0.0679(3) 0.0286(2) 0.0114(2) -0.0062(3) S1 0.0986(7) 0.0617(5) 0.0686(6) -0.0090(4) 0.0258(5) -0.0052(5) F2 0.0789(12) 0.0683(11) 0.0874(13) 0.0012(9) -0.0140(10) -0.0217(10) F3 0.0639(11) 0.0876(12) 0.0850(13) -0.0103(11) 0.0007(10) 0.0097(9) F1 0.1042(15) 0.0840(12) 0.0746(12) 0.0219(11) -0.0171(11) -0.0021(11) N2 0.0466(15) 0.0573(15) 0.0517(15) -0.0036(12) -0.0028(12) -0.0034(12) N1 0.0564(15) 0.0541(15) 0.0484(14) 0.0014(12) -0.0062(12) -0.0083(12) N4 0.0585(17) 0.0823(18) 0.0648(17) -0.0020(15) 0.0004(14) -0.0226(14) N3 0.0542(17) 0.0887(18) 0.0667(18) -0.0034(15) -0.0061(13) -0.0228(15) C9 0.0455(18) 0.0499(16) 0.0494(17) -0.0058(14) 0.0053(14) -0.0036(14) C10 0.0509(18) 0.0517(17) 0.0481(17) -0.0020(14) -0.0001(14) 0.0019(15) C7 0.0571(19) 0.0475(16) 0.0548(18) -0.0027(14) 0.0054(14) -0.0078(14) C8 0.077(2) 0.054(2) 0.058(2) 0.0006(17) 0.0005(17) -0.0060(18) C11 0.073(2) 0.0664(19) 0.0468(18) -0.0031(15) -0.0037(15) -0.0185(17) C13 0.078(2) 0.063(2) 0.056(2) 0.0090(16) 0.0055(17) 0.0078(18) C14 0.074(2) 0.088(2) 0.052(2) 0.0052(18) -0.0100(17) 0.007(2) C2 0.077(2) 0.079(2) 0.059(2) 0.0084(18) 0.0096(17) 0.0070(19) C1 0.068(2) 0.067(2) 0.0528(19) 0.0020(16) 0.0135(16) 0.0109(16) C15 0.061(2) 0.079(2) 0.063(2) 0.0010(18) -0.0103(17) -0.0095(17) C12 0.089(2) 0.082(2) 0.060(2) 0.0041(18) -0.0009(19) -0.0260(19) C3 0.092(3) 0.098(3) 0.086(3) 0.024(2) 0.027(2) 0.005(2) C4 0.070(3) 0.130(3) 0.103(3) 0.000(3) 0.032(3) -0.003(2) C6 0.072(3) 0.152(4) 0.079(3) 0.043(3) 0.013(2) 0.015(3) C5 0.069(3) 0.201(5) 0.087(3) 0.033(3) 0.002(2) 0.011(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' 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 C1 S1 C7 99.89(13) . . ? N1 N2 C10 123.5(2) . . ? N3 N2 N1 113.1(2) . . ? N3 N2 C10 123.2(2) . . ? C9 N1 N2 101.5(2) . . ? N3 N4 C9 105.9(2) . . ? N4 N3 N2 106.5(2) . . ? N1 C9 N4 113.1(2) . . ? N1 C9 C7 124.8(2) . . ? N4 C9 C7 122.1(3) . . ? C11 C10 N2 119.4(2) . . ? C11 C10 C15 121.3(3) . . ? C15 C10 N2 119.3(3) . . ? S1 C7 H7 107.5 . . ? C9 C7 S1 111.86(18) . . ? C9 C7 H7 107.5 . . ? C9 C7 C8 113.1(2) . . ? C8 C7 S1 109.3(2) . . ? C8 C7 H7 107.5 . . ? F2 C8 C7 113.0(2) . . ? F3 C8 F2 106.1(3) . . ? F3 C8 C7 111.9(2) . . ? F1 C8 F2 106.8(2) . . ? F1 C8 F3 106.3(2) . . ? F1 C8 C7 112.2(3) . . ? C10 C11 H11 120.8 . . ? C12 C11 C10 118.4(3) . . ? C12 C11 H11 120.8 . . ? C14 C13 Br1 119.4(2) . . ? C14 C13 C12 120.1(3) . . ? C12 C13 Br1 120.5(3) . . ? C13 C14 H14 120.1 . . ? C13 C14 C15 119.8(3) . . ? C15 C14 H14 120.1 . . ? C1 C2 H2 119.8 . . ? C1 C2 C3 120.4(3) . . ? C3 C2 H2 119.8 . . ? C2 C1 S1 119.7(3) . . ? C6 C1 S1 121.3(3) . . ? C6 C1 C2 118.9(3) . . ? C10 C15 H15 120.4 . . ? C14 C15 C10 119.3(3) . . ? C14 C15 H15 120.4 . . ? C11 C12 C13 121.1(3) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C2 C3 H3 119.9 . . ? C4 C3 C2 120.1(4) . . ? C4 C3 H3 119.9 . . ? C3 C4 H4 120.3 . . ? C3 C4 C5 119.3(4) . . ? C5 C4 H4 120.3 . . ? C1 C6 H6 119.8 . . ? C1 C6 C5 120.4(3) . . ? C5 C6 H6 119.8 . . ? C4 C5 H5 119.6 . . ? C6 C5 C4 120.8(4) . . ? C6 C5 H5 119.6 . . ? 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 C13 1.889(3) . ? S1 C7 1.833(3) . ? S1 C1 1.766(3) . ? F2 C8 1.335(3) . ? F3 C8 1.335(3) . ? F1 C8 1.332(3) . ? N2 N1 1.333(3) . ? N2 N3 1.324(3) . ? N2 C10 1.426(3) . ? N1 C9 1.320(3) . ? N4 N3 1.312(3) . ? N4 C9 1.341(3) . ? C9 C7 1.488(4) . ? C10 C11 1.367(4) . ? C10 C15 1.377(4) . ? C7 H7 0.9800 . ? C7 C8 1.501(4) . ? C11 H11 0.9300 . ? C11 C12 1.366(4) . ? C13 C14 1.360(4) . ? C13 C12 1.372(4) . ? C14 H14 0.9300 . ? C14 C15 1.375(4) . ? C2 H2 0.9300 . ? C2 C1 1.368(4) . ? C2 C3 1.384(4) . ? C1 C6 1.364(4) . ? C15 H15 0.9300 . ? C12 H12 0.9300 . ? C3 H3 0.9300 . ? C3 C4 1.353(5) . ? C4 H4 0.9300 . ? C4 C5 1.369(5) . ? C6 H6 0.9300 . ? C6 C5 1.365(5) . ? C5 H5 0.9300 . ? 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 C13 C14 C15 175.8(2) . . . . ? Br1 C13 C12 C11 -175.9(2) . . . . ? S1 C7 C8 F2 -53.6(3) . . . . ? S1 C7 C8 F3 -173.26(19) . . . . ? S1 C7 C8 F1 67.3(3) . . . . ? S1 C1 C6 C5 -179.9(3) . . . . ? N2 N1 C9 N4 0.6(3) . . . . ? N2 N1 C9 C7 -178.3(2) . . . . ? N2 C10 C11 C12 176.9(3) . . . . ? N2 C10 C15 C14 -177.0(3) . . . . ? N1 N2 N3 N4 -0.1(3) . . . . ? N1 N2 C10 C11 -3.7(4) . . . . ? N1 N2 C10 C15 174.5(2) . . . . ? N1 C9 C7 S1 83.7(3) . . . . ? N1 C9 C7 C8 -40.2(4) . . . . ? N4 C9 C7 S1 -95.1(3) . . . . ? N4 C9 C7 C8 141.0(3) . . . . ? N3 N2 N1 C9 -0.3(3) . . . . ? N3 N2 C10 C11 -178.2(3) . . . . ? N3 N2 C10 C15 -0.1(4) . . . . ? N3 N4 C9 N1 -0.7(3) . . . . ? N3 N4 C9 C7 178.2(2) . . . . ? C9 N4 N3 N2 0.4(3) . . . . ? C9 C7 C8 F2 71.7(3) . . . . ? C9 C7 C8 F3 -48.0(3) . . . . ? C9 C7 C8 F1 -167.4(2) . . . . ? C10 N2 N1 C9 -175.3(2) . . . . ? C10 N2 N3 N4 175.0(2) . . . . ? C10 C11 C12 C13 0.3(5) . . . . ? C7 S1 C1 C2 101.2(2) . . . . ? C7 S1 C1 C6 -80.1(3) . . . . ? C11 C10 C15 C14 1.2(4) . . . . ? C13 C14 C15 C10 -0.1(5) . . . . ? C14 C13 C12 C11 0.7(5) . . . . ? C2 C1 C6 C5 -1.2(6) . . . . ? C2 C3 C4 C5 -0.4(6) . . . . ? C1 S1 C7 C9 94.7(2) . . . . ? C1 S1 C7 C8 -139.3(2) . . . . ? C1 C2 C3 C4 0.0(5) . . . . ? C1 C6 C5 C4 0.8(7) . . . . ? C15 C10 C11 C12 -1.2(4) . . . . ? C12 C13 C14 C15 -0.8(5) . . . . ? C3 C2 C1 S1 179.5(2) . . . . ? C3 C2 C1 C6 0.8(5) . . . . ? C3 C4 C5 C6 0.1(7) . . . . ?