#------------------------------------------------------------------------------ #$Date: 2021-11-26 00:59:21 +0200 (Fri, 26 Nov 2021) $ #$Revision: 270880 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/93/7129316.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_7129316 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_sum 'C15 H11 Br F2 N4 O S' _chemical_formula_weight 413.25 _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 _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-10-17 deposited with the CCDC. 2021-11-24 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.839(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.5290(10) _cell_length_b 10.7691(7) _cell_length_c 9.7943(6) _cell_measurement_temperature 293(2) _cell_volume 1632.10(18) _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.850 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_unetI/netI 0.0401 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.850 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 12938 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.850 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.463 _diffrn_reflns_theta_min 2.817 _exptl_absorpt_coefficient_mu 2.678 _exptl_crystal_density_diffrn 1.682 _exptl_crystal_F_000 824 _exptl_crystal_size_max 0.380 _exptl_crystal_size_mid 0.320 _exptl_crystal_size_min 0.290 _refine_diff_density_max 0.914 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.063 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 218 _refine_ls_number_reflns 3856 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.013 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0456 _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^)+(0.0400P)^2^+1.5997P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0923 _refine_ls_wR_factor_ref 0.1042 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2624 _reflns_number_total 3856 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1cc05890h2.cif _cod_data_source_block shs _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7129316 _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_min 0.429 _shelx_estimated_absorpt_t_max 0.511 _shelx_res_file ; TITL shs_a.res in P2(1)/c shs.res created by SHELXL-2018/3 at 20:18:58 on 18-Apr-2021 REM Old TITL shs in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.216, Rweak 0.031, Alpha 0.034 REM 0.604 for 192 systematic absences, Orientation as input REM Formula found by SHELXT: C17 N2 O4 Br CELL 0.71073 15.529 10.7691 9.7943 90 94.839 90 ZERR 4 0.001 0.0007 0.0006 0 0.005 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Br F N O S UNIT 60 44 4 8 16 4 4 L.S. 4 0 0 PLAN 5 SIZE 0.38 0.32 0.29 CONF BOND list 4 fmap 2 53 MORE -1 ACTA BOND $H OMIT 2 0 0 OMIT 1 1 0 REM REM REM WGHT 0.040000 1.599700 FVAR 0.35986 BR01 3 0.850493 0.810408 0.324842 11.00000 0.04627 0.08016 = 0.05762 0.01243 0.01715 -0.00537 S002 7 0.235817 0.732282 0.933268 11.00000 0.03748 0.06966 = 0.03694 -0.00852 0.00780 0.00014 F003 4 0.326549 0.786088 0.727452 11.00000 0.04658 0.06884 = 0.03805 0.01498 0.00150 -0.00163 F004 4 0.313313 0.589896 0.766304 11.00000 0.04811 0.05082 = 0.07277 -0.02857 0.00645 -0.00697 O005 6 0.428978 0.823182 0.968891 11.00000 0.05300 0.04242 = 0.04481 -0.00399 0.00600 -0.00222 AFIX 147 H005 2 0.440918 0.870071 0.907277 11.00000 -1.50000 AFIX 0 N006 5 0.575172 0.652387 0.692372 11.00000 0.03233 0.02540 = 0.04031 0.00037 0.00631 0.00020 N007 5 0.527572 0.732719 0.756484 11.00000 0.03651 0.02763 = 0.03997 -0.00321 0.00818 0.00206 N008 5 0.558882 0.535116 0.721509 11.00000 0.05523 0.02810 = 0.06665 0.00261 0.02439 0.00276 N009 5 0.498710 0.537619 0.809048 11.00000 0.05803 0.02887 = 0.06932 0.00243 0.02936 0.00156 C00A 1 0.480616 0.658183 0.827518 11.00000 0.03223 0.02697 = 0.03828 0.00172 0.00341 -0.00017 C00B 1 0.411783 0.703231 0.914635 11.00000 0.03835 0.02771 = 0.03372 0.00198 0.00451 -0.00088 AFIX 13 H00B 2 0.408948 0.645458 0.991433 11.00000 -1.20000 AFIX 0 C00C 1 0.638366 0.689156 0.601371 11.00000 0.03123 0.03411 = 0.03666 -0.00224 0.00277 -0.00325 C00D 1 0.324414 0.701494 0.830537 11.00000 0.03910 0.03404 = 0.03370 -0.00325 0.00540 -0.00387 C00E 1 0.652111 0.814359 0.582641 11.00000 0.03931 0.03322 = 0.04970 -0.00114 0.00897 0.00147 AFIX 43 H00E 2 0.620067 0.873268 0.625870 11.00000 -1.20000 AFIX 0 C00F 1 0.149192 0.708913 0.804400 11.00000 0.03376 0.05939 = 0.03535 -0.00378 0.01077 0.00337 C00G 1 0.714689 0.850301 0.498035 11.00000 0.04435 0.03609 = 0.05336 0.00428 0.00648 -0.00404 AFIX 43 H00G 2 0.724965 0.934139 0.483441 11.00000 -1.20000 AFIX 0 C00H 1 0.761687 0.761475 0.435537 11.00000 0.03341 0.05454 = 0.03550 0.00206 0.00276 -0.00516 C00I 1 0.683318 0.600342 0.535970 11.00000 0.04827 0.03375 = 0.06336 -0.00782 0.01804 -0.00446 AFIX 43 H00I 2 0.671786 0.516495 0.548027 11.00000 -1.20000 AFIX 0 C00J 1 0.113961 0.591858 0.783864 11.00000 0.04534 0.06493 = 0.05641 -0.00323 0.00623 -0.00190 AFIX 43 H00J 2 0.135893 0.525567 0.836824 11.00000 -1.20000 AFIX 0 C00K 1 0.115816 0.807589 0.727879 11.00000 0.04725 0.06663 = 0.05961 0.01002 0.01381 0.00949 AFIX 43 H00K 2 0.138341 0.886992 0.742186 11.00000 -1.20000 AFIX 0 C00L 1 0.745715 0.636969 0.452267 11.00000 0.04675 0.04731 = 0.05987 -0.01539 0.01879 -0.00131 AFIX 43 H00L 2 0.776777 0.577962 0.407447 11.00000 -1.20000 AFIX 0 C00M 1 0.046541 0.572816 0.685392 11.00000 0.05463 0.08956 = 0.07320 -0.01990 0.00603 -0.01150 AFIX 43 H00M 2 0.023387 0.493720 0.671588 11.00000 -1.20000 AFIX 0 C00N 1 0.013827 0.669641 0.608352 11.00000 0.04693 0.13078 = 0.05560 -0.02016 0.00499 0.00282 AFIX 43 H00N 2 -0.031608 0.656481 0.541826 11.00000 -1.20000 AFIX 0 C00O 1 0.047497 0.786482 0.628298 11.00000 0.05457 0.10913 = 0.05360 0.01844 0.00811 0.02997 AFIX 43 H00O 2 0.024740 0.852190 0.575217 11.00000 -1.20000 AFIX 0 HKLF 4 REM shs_a.res in P2(1)/c REM wR2 = 0.1042, GooF = S = 1.013, Restrained GooF = 1.013 for all data REM R1 = 0.0456 for 2624 Fo > 4sig(Fo) and 0.0830 for all 3856 data REM 218 parameters refined using 0 restraints END WGHT 0.0399 1.6005 REM Highest difference peak 0.914, deepest hole -0.453, 1-sigma level 0.063 Q1 1 0.4029 0.6041 1.0172 11.00000 0.05 0.91 Q2 1 0.8132 0.8624 0.2781 11.00000 0.05 0.37 Q3 1 0.8420 0.8611 0.2475 11.00000 0.05 0.30 Q4 1 0.2847 0.7200 0.8773 11.00000 0.05 0.29 Q5 1 0.8442 0.7333 0.3044 11.00000 0.05 0.28 ; _shelx_res_checksum 63100 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 Br01 Br 0.85049(2) 0.81041(4) 0.32484(4) 0.06063(15) Uani 1 1 d . . . . . S002 S 0.23582(5) 0.73228(9) 0.93327(8) 0.0478(2) Uani 1 1 d . . . . . F003 F 0.32655(12) 0.78609(18) 0.72745(17) 0.0513(5) Uani 1 1 d . . . . . F004 F 0.31331(12) 0.58990(17) 0.7663(2) 0.0572(5) Uani 1 1 d . . . . . O005 O 0.42898(15) 0.82318(19) 0.9689(2) 0.0466(5) Uani 1 1 d . . . . . H005 H 0.440918 0.870071 0.907277 0.070 Uiso 1 1 calc R U . . . N006 N 0.57517(15) 0.6524(2) 0.6924(2) 0.0325(5) Uani 1 1 d . . . . . N007 N 0.52757(15) 0.7327(2) 0.7565(2) 0.0344(6) Uani 1 1 d . . . . . N008 N 0.55888(19) 0.5351(2) 0.7215(3) 0.0489(7) Uani 1 1 d . . . . . N009 N 0.49871(19) 0.5376(2) 0.8090(3) 0.0507(7) Uani 1 1 d . . . . . C00A C 0.48062(18) 0.6582(2) 0.8275(3) 0.0325(6) Uani 1 1 d . . . . . C00B C 0.41178(19) 0.7032(2) 0.9146(3) 0.0332(6) Uani 1 1 d . . . . . H00B H 0.408948 0.645458 0.991433 0.040 Uiso 1 1 calc R U . . . C00C C 0.63837(18) 0.6892(3) 0.6014(3) 0.0340(6) Uani 1 1 d . . . . . C00D C 0.3244(2) 0.7015(3) 0.8305(3) 0.0355(7) Uani 1 1 d . . . . . C00E C 0.6521(2) 0.8144(3) 0.5826(3) 0.0404(7) Uani 1 1 d . . . . . H00E H 0.620067 0.873268 0.625870 0.049 Uiso 1 1 calc R U . . . C00F C 0.1492(2) 0.7089(3) 0.8044(3) 0.0424(8) Uani 1 1 d . . . . . C00G C 0.7147(2) 0.8503(3) 0.4980(3) 0.0445(8) Uani 1 1 d . . . . . H00G H 0.724965 0.934139 0.483441 0.053 Uiso 1 1 calc R U . . . C00H C 0.7617(2) 0.7615(3) 0.4355(3) 0.0412(7) Uani 1 1 d . . . . . C00I C 0.6833(2) 0.6003(3) 0.5360(3) 0.0477(8) Uani 1 1 d . . . . . H00I H 0.671786 0.516495 0.548027 0.057 Uiso 1 1 calc R U . . . C00J C 0.1140(2) 0.5919(4) 0.7839(4) 0.0554(9) Uani 1 1 d . . . . . H00J H 0.135893 0.525567 0.836824 0.067 Uiso 1 1 calc R U . . . C00K C 0.1158(2) 0.8076(4) 0.7279(4) 0.0573(9) Uani 1 1 d . . . . . H00K H 0.138341 0.886992 0.742186 0.069 Uiso 1 1 calc R U . . . C00L C 0.7457(2) 0.6370(3) 0.4523(4) 0.0505(8) Uani 1 1 d . . . . . H00L H 0.776777 0.577962 0.407447 0.061 Uiso 1 1 calc R U . . . C00M C 0.0465(3) 0.5728(5) 0.6854(5) 0.0724(12) Uani 1 1 d . . . . . H00M H 0.023387 0.493720 0.671588 0.087 Uiso 1 1 calc R U . . . C00N C 0.0138(3) 0.6696(5) 0.6084(4) 0.0777(14) Uani 1 1 d . . . . . H00N H -0.031608 0.656481 0.541826 0.093 Uiso 1 1 calc R U . . . C00O C 0.0475(3) 0.7865(5) 0.6283(4) 0.0722(13) Uani 1 1 d . . . . . H00O H 0.024740 0.852190 0.575217 0.087 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 Br01 0.0463(2) 0.0802(3) 0.0576(2) 0.01243(19) 0.01715(16) -0.00537(18) S002 0.0375(5) 0.0697(6) 0.0369(4) -0.0085(4) 0.0078(3) 0.0001(4) F003 0.0466(11) 0.0688(13) 0.0381(10) 0.0150(9) 0.0015(8) -0.0016(9) F004 0.0481(12) 0.0508(11) 0.0728(13) -0.0286(10) 0.0064(10) -0.0070(9) O005 0.0530(14) 0.0424(13) 0.0448(12) -0.0040(10) 0.0060(11) -0.0022(11) N006 0.0323(13) 0.0254(12) 0.0403(13) 0.0004(10) 0.0063(10) 0.0002(10) N007 0.0365(14) 0.0276(12) 0.0400(13) -0.0032(11) 0.0082(11) 0.0021(10) N008 0.0552(18) 0.0281(14) 0.0667(19) 0.0026(13) 0.0244(15) 0.0028(12) N009 0.0580(18) 0.0289(14) 0.0693(19) 0.0024(13) 0.0294(15) 0.0016(12) C00A 0.0322(15) 0.0270(15) 0.0383(15) 0.0017(12) 0.0034(12) -0.0002(12) C00B 0.0384(16) 0.0277(15) 0.0337(15) 0.0020(12) 0.0045(12) -0.0009(12) C00C 0.0312(15) 0.0341(16) 0.0367(15) -0.0022(13) 0.0028(12) -0.0033(12) C00D 0.0391(16) 0.0340(16) 0.0337(15) -0.0033(13) 0.0054(12) -0.0039(13) C00E 0.0393(17) 0.0332(16) 0.0497(18) -0.0011(14) 0.0090(14) 0.0015(13) C00F 0.0338(17) 0.059(2) 0.0353(16) -0.0038(15) 0.0108(13) 0.0034(15) C00G 0.0444(19) 0.0361(17) 0.0534(19) 0.0043(15) 0.0065(15) -0.0040(14) C00H 0.0334(17) 0.055(2) 0.0355(16) 0.0021(14) 0.0028(13) -0.0052(14) C00I 0.048(2) 0.0338(16) 0.063(2) -0.0078(16) 0.0180(16) -0.0045(15) C00J 0.045(2) 0.065(2) 0.056(2) -0.0032(18) 0.0062(17) -0.0019(18) C00K 0.047(2) 0.067(2) 0.060(2) 0.0100(19) 0.0138(18) 0.0095(18) C00L 0.047(2) 0.047(2) 0.060(2) -0.0154(17) 0.0188(16) -0.0013(16) C00M 0.055(3) 0.090(3) 0.073(3) -0.020(2) 0.006(2) -0.012(2) C00N 0.047(2) 0.131(4) 0.056(2) -0.020(3) 0.0050(19) 0.003(3) C00O 0.055(3) 0.109(4) 0.054(2) 0.018(2) 0.008(2) 0.030(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 C00F S002 C00D 98.32(13) . . ? C00B O005 H005 109.5 . . ? N008 N006 N007 113.3(2) . . ? N008 N006 C00C 123.4(2) . . ? N007 N006 C00C 123.4(2) . . ? C00A N007 N006 101.9(2) . . ? N009 N008 N006 106.2(2) . . ? N008 N009 C00A 105.9(2) . . ? N007 C00A N009 112.7(3) . . ? N007 C00A C00B 123.6(2) . . ? N009 C00A C00B 123.7(2) . . ? O005 C00B C00A 112.8(2) . . ? O005 C00B C00D 110.2(2) . . ? C00A C00B C00D 109.4(2) . . ? O005 C00B H00B 108.1 . . ? C00A C00B H00B 108.1 . . ? C00D C00B H00B 108.1 . . ? C00I C00C C00E 121.9(3) . . ? C00I C00C N006 119.9(3) . . ? C00E C00C N006 118.3(2) . . ? F004 C00D F003 105.0(2) . . ? F004 C00D C00B 109.4(2) . . ? F003 C00D C00B 108.4(2) . . ? F004 C00D S002 110.3(2) . . ? F003 C00D S002 111.0(2) . . ? C00B C00D S002 112.46(19) . . ? C00C C00E C00G 118.5(3) . . ? C00C C00E H00E 120.8 . . ? C00G C00E H00E 120.8 . . ? C00K C00F C00J 119.9(3) . . ? C00K C00F S002 120.2(3) . . ? C00J C00F S002 119.8(3) . . ? C00H C00G C00E 119.8(3) . . ? C00H C00G H00G 120.1 . . ? C00E C00G H00G 120.1 . . ? C00L C00H C00G 121.1(3) . . ? C00L C00H Br01 119.0(2) . . ? C00G C00H Br01 119.9(2) . . ? C00C C00I C00L 119.2(3) . . ? C00C C00I H00I 120.4 . . ? C00L C00I H00I 120.4 . . ? C00M C00J C00F 120.4(4) . . ? C00M C00J H00J 119.8 . . ? C00F C00J H00J 119.8 . . ? C00F C00K C00O 118.9(4) . . ? C00F C00K H00K 120.6 . . ? C00O C00K H00K 120.6 . . ? C00H C00L C00I 119.5(3) . . ? C00H C00L H00L 120.2 . . ? C00I C00L H00L 120.2 . . ? C00N C00M C00J 120.0(4) . . ? C00N C00M H00M 120.0 . . ? C00J C00M H00M 120.0 . . ? C00M C00N C00O 120.3(4) . . ? C00M C00N H00N 119.8 . . ? C00O C00N H00N 119.8 . . ? C00N C00O C00K 120.5(4) . . ? C00N C00O H00O 119.8 . . ? C00K C00O H00O 119.8 . . ? 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 Br01 C00H 1.899(3) . ? S002 C00F 1.783(3) . ? S002 C00D 1.802(3) . ? F003 C00D 1.362(3) . ? F004 C00D 1.361(3) . ? O005 C00B 1.414(3) . ? O005 H005 0.8200 . ? N006 N008 1.324(3) . ? N006 N007 1.329(3) . ? N006 C00C 1.436(4) . ? N007 C00A 1.321(4) . ? N008 N009 1.321(4) . ? N009 C00A 1.344(4) . ? C00A C00B 1.503(4) . ? C00B C00D 1.527(4) . ? C00B H00B 0.9800 . ? C00C C00I 1.374(4) . ? C00C C00E 1.380(4) . ? C00E C00G 1.384(4) . ? C00E H00E 0.9300 . ? C00F C00K 1.376(5) . ? C00F C00J 1.382(5) . ? C00G C00H 1.378(5) . ? C00G H00G 0.9300 . ? C00H C00L 1.376(5) . ? C00I C00L 1.379(4) . ? C00I H00I 0.9300 . ? C00J C00M 1.378(5) . ? C00J H00J 0.9300 . ? C00K C00O 1.398(6) . ? C00K H00K 0.9300 . ? C00L H00L 0.9300 . ? C00M C00N 1.360(6) . ? C00M H00M 0.9300 . ? C00N C00O 1.370(6) . ? C00N H00N 0.9300 . ? C00O H00O 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 N008 N006 N007 C00A 0.0(3) . . . . ? C00C N006 N007 C00A -179.5(3) . . . . ? N007 N006 N008 N009 -0.5(4) . . . . ? C00C N006 N008 N009 179.1(3) . . . . ? N006 N008 N009 C00A 0.7(4) . . . . ? N006 N007 C00A N009 0.4(3) . . . . ? N006 N007 C00A C00B -177.1(3) . . . . ? N008 N009 C00A N007 -0.7(4) . . . . ? N008 N009 C00A C00B 176.8(3) . . . . ? N007 C00A C00B O005 -29.8(4) . . . . ? N009 C00A C00B O005 153.0(3) . . . . ? N007 C00A C00B C00D 93.2(3) . . . . ? N009 C00A C00B C00D -84.0(3) . . . . ? N008 N006 C00C C00I 2.3(4) . . . . ? N007 N006 C00C C00I -178.2(3) . . . . ? N008 N006 C00C C00E -177.6(3) . . . . ? N007 N006 C00C C00E 1.9(4) . . . . ? O005 C00B C00D F004 173.1(2) . . . . ? C00A C00B C00D F004 48.5(3) . . . . ? O005 C00B C00D F003 59.1(3) . . . . ? C00A C00B C00D F003 -65.4(3) . . . . ? O005 C00B C00D S002 -64.0(3) . . . . ? C00A C00B C00D S002 171.51(19) . . . . ? C00F S002 C00D F004 -52.8(2) . . . . ? C00F S002 C00D F003 63.1(2) . . . . ? C00F S002 C00D C00B -175.3(2) . . . . ? C00I C00C C00E C00G -1.7(5) . . . . ? N006 C00C C00E C00G 178.2(3) . . . . ? C00D S002 C00F C00K -92.4(3) . . . . ? C00D S002 C00F C00J 89.4(3) . . . . ? C00C C00E C00G C00H -0.3(5) . . . . ? C00E C00G C00H C00L 2.1(5) . . . . ? C00E C00G C00H Br01 -177.7(2) . . . . ? C00E C00C C00I C00L 1.9(5) . . . . ? N006 C00C C00I C00L -178.0(3) . . . . ? C00K C00F C00J C00M 1.2(5) . . . . ? S002 C00F C00J C00M 179.5(3) . . . . ? C00J C00F C00K C00O -1.3(5) . . . . ? S002 C00F C00K C00O -179.5(3) . . . . ? C00G C00H C00L C00I -1.8(5) . . . . ? Br01 C00H C00L C00I 177.9(3) . . . . ? C00C C00I C00L C00H -0.1(5) . . . . ? C00F C00J C00M C00N -0.5(6) . . . . ? C00J C00M C00N C00O -0.1(6) . . . . ? C00M C00N C00O C00K 0.0(6) . . . . ? C00F C00K C00O C00N 0.7(6) . . . . ?