#------------------------------------------------------------------------------ #$Date: 2018-07-10 12:13:45 +0300 (Tue, 10 Jul 2018) $ #$Revision: 208944 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/21/83/7218365.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_7218365 loop_ _publ_author_name 'Wang, Xiaojuan' 'Zhang, Qi' 'Jiang, Linglei' 'Xu, Yun' 'Mei, Xuefeng' _publ_section_title ; Isostructurality in six celecoxib co-crystals introduced by solvent inclusion ; _journal_issue 48 _journal_name_full CrystEngComm _journal_page_first 10959 _journal_paper_doi 10.1039/C4CE01854K _journal_volume 16 _journal_year 2014 _chemical_formula_sum 'C30.5 H27 F3 N5 O2.5 S' _chemical_formula_weight 502.64 _chemical_name_systematic ; ? ; _space_group_IT_number 15 _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 91.927(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 21.3705(11) _cell_length_b 10.0269(4) _cell_length_c 27.7028(11) _cell_measurement_temperature 296(2) _cell_volume 5932.8(5) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 21794 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.91 _exptl_absorpt_coefficient_mu 0.166 _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2348 _refine_diff_density_max 0.961 _refine_diff_density_min -0.786 _refine_diff_density_rms 0.057 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 390 _refine_ls_number_reflns 5205 _refine_ls_number_restraints 26 _refine_ls_restrained_S_all 1.409 _refine_ls_R_factor_all 0.0839 _refine_ls_R_factor_gt 0.0634 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0848P)^2^+7.8216P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1728 _refine_ls_wR_factor_ref 0.1899 _reflns_number_gt 3905 _reflns_number_total 5205 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c4ce01854k2.cif _cod_data_source_block mo_2014077_0ma _cod_depositor_comments ; Adding full bibliography for 7218359--7218367.cif. 2018-05-16 Z value and formula fixed to values more according to usual chemical conventions. miguel ; _cod_original_formula_sum 'C61 H54 F6 N10 O5 S2' _cod_original_formula_weight 1185.28 _cod_original_formula_units_Z 4 _cod_original_sg_symbol_H-M C2/c _cod_database_code 7218365 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags S1 S 1.06788(4) 0.29350(10) 0.14038(3) 0.0488(3) Uani 1 1 d . O1A O 0.0000 0.6435(10) 0.2500 0.244(7) Uani 1 2 d S F3 F 0.65457(17) 0.0799(5) 0.29944(14) 0.1370(16) Uani 1 1 d . O1 O 1.08584(13) 0.4147(3) 0.16407(11) 0.0668(8) Uani 1 1 d . C11 C 0.7581(2) -0.0075(6) -0.02651(16) 0.0835(15) Uani 1 1 d . H5 H 0.7609 0.0753 -0.0437 0.125 Uiso 1 1 calc R H4 H 0.7192 -0.0507 -0.0353 0.125 Uiso 1 1 calc R H6 H 0.7924 -0.0641 -0.0347 0.125 Uiso 1 1 calc R O2 O 1.05953(14) 0.2905(3) 0.08892(10) 0.0673(8) Uani 1 1 d . N2 N 0.81589(13) 0.1402(3) 0.20685(11) 0.0492(8) Uani 1 1 d . C5 C 0.76654(16) 0.0673(4) 0.12712(13) 0.0491(9) Uani 1 1 d . N3 N 1.11843(16) 0.1835(4) 0.15419(15) 0.0588(9) Uani 1 1 d . N1 N 0.80204(15) 0.1535(4) 0.25390(12) 0.0628(9) Uani 1 1 d . F1 F 0.7214(4) 0.2000(9) 0.3283(3) 0.298(4) Uani 1 1 d U N2' N 0.9347(2) 0.7984(4) 0.11169(16) 0.0802(12) Uani 1 1 d . C10' C 0.9547(3) 0.6768(5) 0.11944(18) 0.0859(16) Uani 1 1 d . H9' H 0.9741 0.6587 0.1493 0.103 Uiso 1 1 calc R C9' C 0.9493(2) 0.5741(5) 0.08707(17) 0.0752(13) Uani 1 1 d . H10' H 0.9641 0.4897 0.0954 0.090 Uiso 1 1 calc R C8' C 0.92196(17) 0.5958(4) 0.04239(14) 0.0520(9) Uani 1 1 d . C7' C 0.91314(19) 0.4948(5) 0.00431(16) 0.0644(11) Uani 1 1 d . H6' H 0.8964 0.5234 -0.0253 0.077 Uiso 1 1 calc R C6' C 0.9266(2) 0.3706(5) 0.00857(17) 0.0675(12) Uani 1 1 d . H5' H 0.9443 0.3425 0.0380 0.081 Uiso 1 1 calc R C3' C 0.91649(18) 0.2676(4) -0.02948(15) 0.0584(10) Uani 1 1 d . C4' C 0.8892(2) 0.2897(5) -0.07459(18) 0.0735(13) Uani 1 1 d . H3' H 0.8767 0.3753 -0.0835 0.088 Uiso 1 1 calc R C5' C 0.8805(2) 0.1847(5) -0.10674(18) 0.0760(13) Uani 1 1 d . H4' H 0.8612 0.2022 -0.1366 0.091 Uiso 1 1 calc R N1' N 0.89838(17) 0.0604(4) -0.09694(14) 0.0665(10) Uani 1 1 d . C11' C 0.9081(3) 0.8195(5) 0.0686(2) 0.0813(14) Uani 1 1 d . H8' H 0.8931 0.9047 0.0617 0.098 Uiso 1 1 calc R C12' C 0.9012(2) 0.7239(5) 0.03342(18) 0.0722(12) Uani 1 1 d . H7' H 0.8825 0.7454 0.0036 0.087 Uiso 1 1 calc R C2' C 0.9341(2) 0.1391(5) -0.01993(17) 0.0667(11) Uani 1 1 d . H2' H 0.9531 0.1179 0.0098 0.080 Uiso 1 1 calc R C1' C 0.9240(2) 0.0415(5) -0.05364(18) 0.0686(12) Uani 1 1 d . H1' H 0.9361 -0.0448 -0.0454 0.082 Uiso 1 1 calc R C2A C 0.0000 0.7602(14) 0.2500 0.137(5) Uani 1 2 d S C15 C 0.99473(15) 0.2449(4) 0.16319(12) 0.0427(8) Uani 1 1 d . C14 C 0.96857(17) 0.1244(4) 0.14825(14) 0.0502(9) Uani 1 1 d . H10 H 0.9905 0.0678 0.1283 0.060 Uiso 1 1 calc R C13 C 0.90981(17) 0.0889(4) 0.16316(14) 0.0508(9) Uani 1 1 d . H9 H 0.8920 0.0081 0.1535 0.061 Uiso 1 1 calc R C12 C 0.87772(15) 0.1747(4) 0.19250(13) 0.0445(8) Uani 1 1 d . C3 C 0.76657(17) 0.0899(4) 0.17955(14) 0.0518(9) Uani 1 1 d . C10 C 0.78969(18) 0.1603(4) 0.09480(15) 0.0559(10) Uani 1 1 d . H8 H 0.8074 0.2394 0.1064 0.067 Uiso 1 1 calc R C9 C 0.78648(18) 0.1357(4) 0.04587(15) 0.0603(11) Uani 1 1 d . H7 H 0.8020 0.1991 0.0249 0.072 Uiso 1 1 calc R C8 C 0.76073(18) 0.0193(5) 0.02701(15) 0.0590(10) Uani 1 1 d . C16 C 0.96342(16) 0.3275(4) 0.19407(13) 0.0467(9) Uani 1 1 d . H11 H 0.9818 0.4067 0.2048 0.056 Uiso 1 1 calc R C17 C 0.90439(17) 0.2919(4) 0.20895(13) 0.0483(9) Uani 1 1 d . H12 H 0.8830 0.3468 0.2299 0.058 Uiso 1 1 calc R C1 C 0.7434(2) 0.1103(5) 0.25582(16) 0.0727(13) Uani 1 1 d . C2 C 0.7193(2) 0.0701(5) 0.21084(16) 0.0685(12) Uani 1 1 d . H1 H 0.6794 0.0369 0.2036 0.082 Uiso 1 1 calc R C7 C 0.73714(19) -0.0712(4) 0.05940(15) 0.0613(11) Uani 1 1 d . H3 H 0.7191 -0.1497 0.0477 0.074 Uiso 1 1 calc R C6 C 0.73965(18) -0.0483(4) 0.10866(15) 0.0565(10) Uani 1 1 d . H2 H 0.7232 -0.1109 0.1295 0.068 Uiso 1 1 calc R C4 C 0.7102(3) 0.1169(11) 0.3008(2) 0.144(3) Uani 1 1 d U F2 F 0.7337(4) 0.0175(12) 0.3298(2) 0.285(4) Uani 1 1 d U C1A C 0.0518(6) 0.8378(14) 0.2326(4) 0.214(5) Uani 1 1 d . H1A1 H 0.0877 0.8262 0.2540 0.321 Uiso 1 1 calc R H1A2 H 0.0403 0.9304 0.2315 0.321 Uiso 1 1 calc R H1A3 H 0.0616 0.8083 0.2008 0.321 Uiso 1 1 calc R H14 H 1.133(2) 0.184(5) 0.1832(18) 0.072(14) Uiso 1 1 d . H13 H 1.118(2) 0.107(5) 0.1382(17) 0.077(15) Uiso 1 1 d . 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 S1 0.0413(5) 0.0504(6) 0.0545(6) 0.0043(4) -0.0018(4) -0.0041(4) O1A 0.47(2) 0.104(7) 0.146(8) 0.000 -0.103(10) 0.000 F3 0.092(2) 0.196(4) 0.126(3) -0.049(3) 0.047(2) -0.076(3) O1 0.0538(16) 0.0538(17) 0.093(2) -0.0063(15) 0.0054(14) -0.0154(13) C11 0.076(3) 0.110(4) 0.064(3) -0.008(3) 0.000(2) -0.001(3) O2 0.0648(18) 0.084(2) 0.0530(16) 0.0150(14) 0.0004(13) 0.0002(15) N2 0.0389(16) 0.0554(19) 0.0530(18) -0.0050(15) -0.0046(13) -0.0099(14) C5 0.0382(18) 0.053(2) 0.056(2) 0.0032(17) -0.0104(15) -0.0044(16) N3 0.0468(19) 0.066(2) 0.063(2) -0.0088(19) -0.0103(16) 0.0077(16) N1 0.0501(19) 0.081(3) 0.057(2) -0.0115(17) 0.0023(15) -0.0212(18) F1 0.313(7) 0.380(8) 0.213(5) -0.225(5) 0.190(5) -0.274(6) N2' 0.093(3) 0.067(3) 0.080(3) -0.023(2) 0.009(2) 0.001(2) C10' 0.122(5) 0.078(4) 0.058(3) -0.012(2) -0.012(3) 0.012(3) C9' 0.098(4) 0.059(3) 0.068(3) -0.005(2) -0.008(2) 0.017(2) C8' 0.045(2) 0.056(2) 0.055(2) -0.0102(18) 0.0051(17) -0.0012(17) C7' 0.057(2) 0.065(3) 0.071(3) -0.001(2) 0.003(2) 0.000(2) C6' 0.064(3) 0.068(3) 0.070(3) 0.003(2) -0.001(2) 0.006(2) C3' 0.048(2) 0.063(3) 0.064(3) -0.013(2) 0.0046(18) -0.0016(19) C4' 0.081(3) 0.052(3) 0.087(3) -0.005(2) 0.006(3) 0.015(2) C5' 0.080(3) 0.082(4) 0.066(3) -0.008(2) -0.006(2) 0.010(3) N1' 0.061(2) 0.064(2) 0.074(2) -0.0175(19) 0.0033(18) 0.0021(18) C11' 0.084(3) 0.048(3) 0.111(4) -0.005(3) -0.002(3) 0.006(2) C12' 0.074(3) 0.068(3) 0.074(3) 0.006(2) -0.013(2) 0.000(2) C2' 0.065(3) 0.065(3) 0.070(3) -0.008(2) -0.004(2) 0.004(2) C1' 0.067(3) 0.056(3) 0.083(3) -0.004(2) 0.002(2) 0.007(2) C2A 0.248(16) 0.105(9) 0.055(5) 0.000 -0.033(7) 0.000 C15 0.0382(17) 0.0427(19) 0.0466(19) 0.0005(15) -0.0090(14) 0.0003(15) C14 0.045(2) 0.047(2) 0.059(2) -0.0104(17) -0.0001(16) 0.0012(16) C13 0.045(2) 0.042(2) 0.064(2) -0.0079(17) -0.0042(17) -0.0061(16) C12 0.0379(18) 0.045(2) 0.050(2) 0.0012(16) -0.0066(15) -0.0046(15) C3 0.043(2) 0.051(2) 0.060(2) -0.0007(18) -0.0079(17) -0.0092(17) C10 0.048(2) 0.054(2) 0.065(3) 0.0057(19) -0.0095(18) -0.0093(18) C9 0.049(2) 0.070(3) 0.062(3) 0.013(2) -0.0047(18) -0.005(2) C8 0.046(2) 0.072(3) 0.058(2) -0.002(2) -0.0066(17) 0.004(2) C16 0.0447(19) 0.041(2) 0.054(2) -0.0041(16) -0.0045(16) -0.0059(16) C17 0.046(2) 0.044(2) 0.055(2) -0.0077(16) 0.0004(16) -0.0019(16) C1 0.055(2) 0.100(4) 0.063(3) -0.017(2) 0.005(2) -0.032(2) C2 0.048(2) 0.089(3) 0.068(3) -0.002(2) -0.0027(19) -0.026(2) C7 0.057(2) 0.058(3) 0.068(3) -0.006(2) -0.015(2) -0.0070(19) C6 0.052(2) 0.052(2) 0.065(3) 0.0076(19) -0.0110(18) -0.0099(18) C4 0.115(5) 0.250(9) 0.068(4) -0.033(5) 0.012(3) -0.121(6) F2 0.224(6) 0.513(11) 0.123(4) 0.105(6) 0.073(4) 0.060(7) C1A 0.259(15) 0.234(14) 0.151(9) 0.002(9) 0.023(9) -0.025(11) 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' 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_3 O1 S1 O2 119.88(19) . O1 S1 N3 108.2(2) . O2 S1 N3 106.7(2) . O1 S1 C15 107.25(17) . O2 S1 C15 105.50(16) . N3 S1 C15 108.97(19) . C8 C11 H5 109.5 . C8 C11 H4 109.5 . H5 C11 H4 109.5 . C8 C11 H6 109.5 . H5 C11 H6 109.5 . H4 C11 H6 109.5 . N1 N2 C3 112.2(3) . N1 N2 C12 118.4(3) . C3 N2 C12 129.3(3) . C6 C5 C10 118.3(4) . C6 C5 C3 118.7(3) . C10 C5 C3 122.9(3) . S1 N3 H14 117(3) . S1 N3 H13 119(3) . H14 N3 H13 119(4) . C1 N1 N2 104.1(3) . C10' N2' C11' 115.2(4) . N2' C10' C9' 125.1(5) . N2' C10' H9' 117.5 . C9' C10' H9' 117.5 . C10' C9' C8' 119.8(4) . C10' C9' H10' 120.1 . C8' C9' H10' 120.1 . C9' C8' C12' 115.9(4) . C9' C8' C7' 125.5(4) . C12' C8' C7' 118.7(4) . C6' C7' C8' 125.4(4) . C6' C7' H6' 117.3 . C8' C7' H6' 117.3 . C7' C6' C3' 125.6(4) . C7' C6' H5' 117.2 . C3' C6' H5' 117.2 . C2' C3' C4' 115.6(4) . C2' C3' C6' 119.0(4) . C4' C3' C6' 125.3(4) . C3' C4' C5' 120.2(4) . C3' C4' H3' 119.9 . C5' C4' H3' 119.9 . N1' C5' C4' 123.3(4) . N1' C5' H4' 118.3 . C4' C5' H4' 118.3 . C1' N1' C5' 115.4(4) . N2' C11' C12' 124.3(5) . N2' C11' H8' 117.9 . C12' C11' H8' 117.9 . C11' C12' C8' 119.8(4) . C11' C12' H7' 120.1 . C8' C12' H7' 120.1 . C1' C2' C3' 120.5(4) . C1' C2' H2' 119.7 . C3' C2' H2' 119.7 . N1' C1' C2' 124.9(4) . N1' C1' H1' 117.6 . C2' C1' H1' 117.6 . O1A C2A C1A 122.5(7) . O1A C2A C1A 122.5(7) 2 C1A C2A C1A 115.0(14) 2 C16 C15 C14 120.6(3) . C16 C15 S1 120.5(3) . C14 C15 S1 118.9(3) . C13 C14 C15 119.7(3) . C13 C14 H10 120.1 . C15 C14 H10 120.1 . C14 C13 C12 119.3(3) . C14 C13 H9 120.3 . C12 C13 H9 120.3 . C17 C12 C13 121.2(3) . C17 C12 N2 119.3(3) . C13 C12 N2 119.5(3) . C2 C3 N2 105.9(3) . C2 C3 C5 128.9(3) . N2 C3 C5 125.1(3) . C9 C10 C5 120.3(4) . C9 C10 H8 119.8 . C5 C10 H8 119.8 . C10 C9 C8 121.9(4) . C10 C9 H7 119.1 . C8 C9 H7 119.1 . C7 C8 C9 117.2(4) . C7 C8 C11 121.3(4) . C9 C8 C11 121.5(4) . C15 C16 C17 119.6(3) . C15 C16 H11 120.2 . C17 C16 H11 120.2 . C12 C17 C16 119.5(3) . C12 C17 H12 120.3 . C16 C17 H12 120.3 . N1 C1 C2 112.3(4) . N1 C1 C4 120.4(4) . C2 C1 C4 127.2(4) . C3 C2 C1 105.5(4) . C3 C2 H1 127.3 . C1 C2 H1 127.3 . C8 C7 C6 121.9(4) . C8 C7 H3 119.1 . C6 C7 H3 119.1 . C7 C6 C5 120.4(4) . C7 C6 H2 119.8 . C5 C6 H2 119.8 . F1 C4 F3 114.4(8) . F1 C4 F2 94.4(8) . F3 C4 F2 97.7(7) . F1 C4 C1 120.3(6) . F3 C4 C1 116.8(5) . F2 C4 C1 106.8(8) . C2A C1A H1A1 109.5 . C2A C1A H1A2 109.5 . H1A1 C1A H1A2 109.5 . C2A C1A H1A3 109.5 . H1A1 C1A H1A3 109.5 . H1A2 C1A H1A3 109.5 . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 O1 1.428(3) . S1 O2 1.431(3) . S1 N3 1.582(4) . S1 C15 1.774(4) . O1A C2A 1.170(13) . F3 C4 1.245(6) . C11 C8 1.506(6) . C11 H5 0.9600 . C11 H4 0.9600 . C11 H6 0.9600 . N2 N1 1.353(4) . N2 C3 1.372(4) . N2 C12 1.435(4) . C5 C6 1.384(5) . C5 C10 1.395(5) . C5 C3 1.470(5) . N3 H14 0.85(5) . N3 H13 0.89(5) . N1 C1 1.330(5) . F1 C4 1.148(8) . N2' C10' 1.308(6) . N2' C11' 1.322(7) . C10' C9' 1.368(6) . C10' H9' 0.9300 . C9' C8' 1.368(6) . C9' H10' 0.9300 . C8' C12' 1.380(6) . C8' C7' 1.469(6) . C7' C6' 1.283(6) . C7' H6' 0.9300 . C6' C3' 1.486(6) . C6' H5' 0.9300 . C3' C2' 1.366(6) . C3' C4' 1.379(6) . C4' C5' 1.387(6) . C4' H3' 0.9300 . C5' N1' 1.329(6) . C5' H4' 0.9300 . N1' C1' 1.315(6) . C11' C12' 1.371(7) . C11' H8' 0.9300 . C12' H7' 0.9300 . C2' C1' 1.365(6) . C2' H2' 0.9300 . C1' H1' 0.9300 . C2A C1A 1.448(12) . C2A C1A 1.448(12) 2 C15 C16 1.380(5) . C15 C14 1.389(5) . C14 C13 1.382(5) . C14 H10 0.9300 . C13 C12 1.382(5) . C13 H9 0.9300 . C12 C17 1.377(5) . C3 C2 1.368(6) . C10 C9 1.377(6) . C10 H8 0.9300 . C9 C8 1.386(6) . C9 H7 0.9300 . C8 C7 1.383(6) . C16 C17 1.387(5) . C16 H11 0.9300 . C17 H12 0.9300 . C1 C2 1.392(6) . C1 C4 1.457(8) . C2 H1 0.9300 . C7 C6 1.383(6) . C7 H3 0.9300 . C6 H2 0.9300 . C4 F2 1.364(12) . C1A H1A1 0.9600 . C1A H1A2 0.9600 . C1A H1A3 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 C3 N2 N1 C1 0.3(5) C12 N2 N1 C1 -178.0(4) C11' N2' C10' C9' -0.7(9) N2' C10' C9' C8' 1.0(9) C10' C9' C8' C12' -0.3(7) C10' C9' C8' C7' -180.0(5) C9' C8' C7' C6' 4.2(7) C12' C8' C7' C6' -175.6(4) C8' C7' C6' C3' 178.6(4) C7' C6' C3' C2' 179.0(5) C7' C6' C3' C4' -2.1(7) C2' C3' C4' C5' 0.8(7) C6' C3' C4' C5' -178.1(4) C3' C4' C5' N1' -1.4(8) C4' C5' N1' C1' 1.6(7) C10' N2' C11' C12' -0.2(8) N2' C11' C12' C8' 0.9(8) C9' C8' C12' C11' -0.6(7) C7' C8' C12' C11' 179.1(4) C4' C3' C2' C1' -0.6(6) C6' C3' C2' C1' 178.3(4) C5' N1' C1' C2' -1.5(7) C3' C2' C1' N1' 1.0(7) O1 S1 C15 C16 6.3(3) O2 S1 C15 C16 -122.6(3) N3 S1 C15 C16 123.1(3) O1 S1 C15 C14 -175.8(3) O2 S1 C15 C14 55.3(3) N3 S1 C15 C14 -58.9(3) C16 C15 C14 C13 2.1(5) S1 C15 C14 C13 -175.8(3) C15 C14 C13 C12 0.5(6) C14 C13 C12 C17 -3.0(6) C14 C13 C12 N2 178.1(3) N1 N2 C12 C17 -45.8(5) C3 N2 C12 C17 136.3(4) N1 N2 C12 C13 133.1(4) C3 N2 C12 C13 -44.8(6) N1 N2 C3 C2 -0.1(5) C12 N2 C3 C2 177.9(4) N1 N2 C3 C5 178.3(4) C12 N2 C3 C5 -3.7(6) C6 C5 C3 C2 -43.5(6) C10 C5 C3 C2 133.3(5) C6 C5 C3 N2 138.4(4) C10 C5 C3 N2 -44.8(6) C6 C5 C10 C9 -1.0(6) C3 C5 C10 C9 -177.8(4) C5 C10 C9 C8 -0.2(6) C10 C9 C8 C7 1.1(6) C10 C9 C8 C11 -179.3(4) C14 C15 C16 C17 -2.2(5) S1 C15 C16 C17 175.7(3) C13 C12 C17 C16 2.9(5) N2 C12 C17 C16 -178.2(3) C15 C16 C17 C12 -0.3(5) N2 N1 C1 C2 -0.3(6) N2 N1 C1 C4 -176.3(7) N2 C3 C2 C1 -0.1(5) C5 C3 C2 C1 -178.4(4) N1 C1 C2 C3 0.3(6) C4 C1 C2 C3 175.8(7) C9 C8 C7 C6 -0.9(6) C11 C8 C7 C6 179.6(4) C8 C7 C6 C5 -0.3(6) C10 C5 C6 C7 1.2(6) C3 C5 C6 C7 178.1(4) N1 C1 C4 F1 30.7(16) C2 C1 C4 F1 -144.6(10) N1 C1 C4 F3 177.0(7) C2 C1 C4 F3 1.8(14) N1 C1 C4 F2 -75.0(9) C2 C1 C4 F2 109.8(8)