#------------------------------------------------------------------------------ #$Date: 2016-02-21 00:03:34 +0000 (Sun, 21 Feb 2016) $ #$Revision: 176798 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/90/2239018.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_2239018 loop_ _publ_author_name 'de Oliveira, Adriano Bof' 'Feitosa, B\'arbara Regina Santos' 'N\"ather, Christian' 'Jess, Inke' _publ_section_title ; N-Phenyl-2-(1,2,3,4-tetrahydronaphthalen-1-ylidene)hydrazinecarbothioamide ; _journal_coeditor_code BT6959 _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o205 _journal_paper_doi 10.1107/S1600536814001585 _journal_volume 70 _journal_year 2014 _chemical_formula_iupac 'C17 H17 N3 S' _chemical_formula_moiety 'C17 H17 N3 S' _chemical_formula_sum 'C17 H17 N3 S' _chemical_formula_weight 295.40 _chemical_melting_point 452 _chemical_name_systematic N-Phenyl-2-(1,2,3,4-tetrahydronaphthalen-1-ylidene)hydrazinecarbothioamide _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 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 107.495(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.4415(3) _cell_length_b 18.0256(7) _cell_length_c 10.0260(3) _cell_measurement_reflns_used 26099 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 28.07 _cell_measurement_theta_min 2.26 _cell_volume 1455.02(9) _computing_cell_refinement 'X-AREA (Stoe & Cie, 2008)' _computing_data_collection 'X-AREA (Stoe & Cie, 2008)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2006)' _computing_publication_material 'publCIF (Westrip, 2010)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 200(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Stoe IPDS-1' _diffrn_measurement_method '\f scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0685 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 23139 _diffrn_reflns_theta_full 28.07 _diffrn_reflns_theta_max 28.07 _diffrn_reflns_theta_min 2.26 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_description cubic _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.258 _refine_diff_density_min -0.239 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 3520 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.050 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0358 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+0.4190P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0847 _refine_ls_wR_factor_ref 0.0889 _reflns_number_gt 3045 _reflns_number_total 3520 _reflns_threshold_expression I>2sigma(I) _iucr_refine_instructions_details ; TITL C17H17N3S at 200 K in P2(1)/n (TPTSC) CELL 0.71073 8.4415 18.0256 10.0260 90.000 107.495 90.000 ZERR 4.00 0.0003 0.0007 0.0003 0.000 0.002 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N S UNIT 68 68 12 4 L.S. 10 ACTA TEMP -73 BOND $H CONF EQIV $1 -x+1, -y, -z+1 HTAB N1 S1_$1 HTAB N3 N2 MPLA C1 N1 N2 N3 S1 MPLA C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 MPLA C6 C7 C8 C9 C10 C11 MPLA C12 C13 C14 C15 C16 C17 WGHT 0.037100 0.419000 FVAR 1.15019 S1 4 0.377838 0.093512 0.541945 11.00000 0.04258 0.04362 = 0.02103 -0.00099 0.00155 0.01742 C1 1 0.476885 0.073659 0.709806 11.00000 0.02387 0.03133 = 0.02482 -0.00004 0.00599 0.00190 N1 3 0.556489 0.007336 0.744405 11.00000 0.02905 0.03060 = 0.02229 -0.00058 0.00292 0.00484 AFIX 3 H1N 2 0.570319 -0.019464 0.675385 11.00000 -1.20000 AFIX 0 N2 3 0.658456 -0.001087 0.880383 11.00000 0.02775 0.03106 = 0.02228 0.00237 0.00403 0.00174 C2 1 0.748366 -0.060100 0.911513 11.00000 0.02430 0.02579 = 0.02459 0.00223 0.00697 -0.00147 C3 1 0.747319 -0.122138 0.810712 11.00000 0.03128 0.02841 = 0.02615 -0.00026 0.00663 -0.00188 AFIX 23 H3A 2 0.808515 -0.106139 0.745530 11.00000 -1.20000 H3B 2 0.631247 -0.132710 0.754851 11.00000 -1.20000 AFIX 0 C4 1 0.826143 -0.192831 0.884891 11.00000 0.03969 0.02659 = 0.03314 -0.00018 0.01251 0.00210 AFIX 23 H4A 2 0.756092 -0.213394 0.939403 11.00000 -1.20000 H4B 2 0.833709 -0.230332 0.814921 11.00000 -1.20000 AFIX 0 C5 1 0.998523 -0.176057 0.982012 11.00000 0.03426 0.03599 = 0.03954 0.00453 0.01265 0.00903 AFIX 23 H5A 2 1.048256 -0.222006 1.031081 11.00000 -1.20000 H5B 2 1.070179 -0.158316 0.926514 11.00000 -1.20000 AFIX 0 C6 1 0.990931 -0.117856 1.087928 11.00000 0.02521 0.02893 = 0.03153 0.00693 0.00819 -0.00167 C7 1 1.106596 -0.117329 1.220970 11.00000 0.02535 0.03859 = 0.03771 0.01307 0.00378 -0.00137 AFIX 43 H7 2 1.192944 -0.153246 1.243534 11.00000 -1.20000 AFIX 0 C8 1 1.098245 -0.065774 1.320423 11.00000 0.03642 0.04138 = 0.02920 0.01007 -0.00199 -0.01206 AFIX 43 H8 2 1.179558 -0.065652 1.409668 11.00000 -1.20000 AFIX 0 C9 1 0.970885 -0.014298 1.289471 11.00000 0.05095 0.03179 = 0.02663 0.00025 0.00371 -0.00756 AFIX 43 H9 2 0.962693 0.020318 1.358542 11.00000 -1.20000 AFIX 0 C10 1 0.855142 -0.013126 1.157807 11.00000 0.04052 0.02678 = 0.02877 0.00186 0.00500 0.00094 AFIX 43 H10 2 0.768373 0.022585 1.137025 11.00000 -1.20000 AFIX 0 C11 1 0.864940 -0.064060 1.055230 11.00000 0.02628 0.02550 = 0.02542 0.00443 0.00578 -0.00271 N3 3 0.489696 0.119018 0.818783 11.00000 0.02943 0.03373 = 0.02018 0.00016 0.00193 0.00721 AFIX 43 H2N 2 0.551289 0.102849 0.900800 11.00000 -1.20000 AFIX 0 C12 1 0.416009 0.189853 0.817804 11.00000 0.02627 0.02970 = 0.02053 0.00084 0.00692 0.00303 C13 1 0.512583 0.246623 0.894852 11.00000 0.02478 0.03909 = 0.02424 -0.00187 0.00332 -0.00010 AFIX 43 H13 2 0.626650 0.238216 0.942689 11.00000 -1.20000 AFIX 0 C14 1 0.442704 0.315487 0.901994 11.00000 0.03604 0.03228 = 0.03103 -0.00584 0.00575 -0.00375 AFIX 43 H14 2 0.508859 0.354154 0.955117 11.00000 -1.20000 AFIX 0 C15 1 0.276395 0.328127 0.831782 11.00000 0.03826 0.03027 = 0.03180 -0.00124 0.00862 0.00547 AFIX 43 H15 2 0.228439 0.375396 0.836165 11.00000 -1.20000 AFIX 0 C16 1 0.181009 0.271356 0.755367 11.00000 0.02628 0.03877 = 0.02917 -0.00120 0.00442 0.00543 AFIX 43 H16 2 0.067105 0.279887 0.707122 11.00000 -1.20000 AFIX 0 C17 1 0.249529 0.202206 0.748315 11.00000 0.02546 0.03231 = 0.02659 -0.00356 0.00579 -0.00139 AFIX 43 H17 2 0.182774 0.163435 0.696121 11.00000 -1.20000 HKLF 4 REM C17H17N3S at 200 K in P2(1)/n (TPTSC) REM R1 = 0.0358 for 3045 Fo > 4sig(Fo) and 0.0454 for all 3520 data REM 190 parameters refined using 0 restraints END WGHT 0.0371 0.4190 REM Highest difference peak 0.258, deepest hole -0.239, 1-sigma level 0.037 Q1 1 0.7431 -0.0921 0.8606 11.00000 0.05 0.26 Q2 1 0.8359 -0.0421 1.1052 11.00000 0.05 0.21 Q3 1 0.9980 -0.1418 1.0361 11.00000 0.05 0.21 Q4 1 0.4571 0.1609 0.8039 11.00000 0.05 0.20 Q5 1 0.9144 -0.0980 1.0851 11.00000 0.05 0.20 Q6 1 0.4529 0.2162 0.8665 11.00000 0.05 0.19 Q7 1 0.2292 0.2427 0.7255 11.00000 0.05 0.19 Q8 1 0.7794 -0.1569 0.8479 11.00000 0.05 0.19 Q9 1 0.3914 0.1567 0.5783 11.00000 0.05 0.19 Q10 1 0.4666 0.0944 0.7642 11.00000 0.05 0.18 Q11 1 0.4025 0.0357 0.5223 11.00000 0.05 0.17 Q12 1 0.3638 0.0423 0.5035 11.00000 0.05 0.17 Q13 1 0.3234 0.0527 0.5665 11.00000 0.05 0.17 Q14 1 0.3798 0.1560 0.5245 11.00000 0.05 0.17 Q15 1 0.3241 0.1355 0.5591 11.00000 0.05 0.16 Q16 1 1.0468 -0.1187 1.1533 11.00000 0.05 0.16 Q17 1 1.0796 -0.0987 1.2825 11.00000 0.05 0.16 Q18 1 0.4799 0.2845 0.8781 11.00000 0.05 0.16 Q19 1 0.3484 0.2012 0.7579 11.00000 0.05 0.16 Q20 1 0.4616 0.2741 0.9089 11.00000 0.05 0.16 ; _cod_data_source_file bt6959sup1.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2239018 _cod_database_fobs_code 2239018 loop_ _symmetry_equiv_pos_as_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_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity S S1 0.37784(5) 0.09351(2) 0.54195(3) 0.03751(11) Uani d . 1 1 C C1 0.47689(15) 0.07366(7) 0.70981(13) 0.0270(3) Uani d . 1 1 N N1 0.55649(13) 0.00734(6) 0.74440(11) 0.0284(2) Uani d . 1 1 H H1N 0.5703 -0.0195 0.6754 0.034 Uiso d R 1 1 N N2 0.65846(13) -0.00109(6) 0.88038(11) 0.0278(2) Uani d . 1 1 C C2 0.74837(15) -0.06010(7) 0.91151(12) 0.0250(2) Uani d . 1 1 C C3 0.74732(17) -0.12214(7) 0.81071(13) 0.0291(3) Uani d . 1 1 H H3A 0.8085 -0.1061 0.7455 0.035 Uiso calc R 1 1 H H3B 0.6312 -0.1327 0.7549 0.035 Uiso calc R 1 1 C C4 0.82614(18) -0.19283(7) 0.88489(14) 0.0328(3) Uani d . 1 1 H H4A 0.7561 -0.2134 0.9394 0.039 Uiso calc R 1 1 H H4B 0.8337 -0.2303 0.8149 0.039 Uiso calc R 1 1 C C5 0.99852(18) -0.17606(8) 0.98201(15) 0.0363(3) Uani d . 1 1 H H5A 1.0483 -0.2220 1.0311 0.044 Uiso calc R 1 1 H H5B 1.0702 -0.1583 0.9265 0.044 Uiso calc R 1 1 C C6 0.99093(16) -0.11786(7) 1.08793(14) 0.0286(3) Uani d . 1 1 C C7 1.10660(17) -0.11733(8) 1.22097(15) 0.0351(3) Uani d . 1 1 H H7 1.1929 -0.1532 1.2435 0.042 Uiso calc R 1 1 C C8 1.09825(18) -0.06577(8) 1.32042(15) 0.0383(3) Uani d . 1 1 H H8 1.1796 -0.0657 1.4097 0.046 Uiso calc R 1 1 C C9 0.9709(2) -0.01430(8) 1.28947(14) 0.0382(3) Uani d . 1 1 H H9 0.9627 0.0203 1.3585 0.046 Uiso calc R 1 1 C C10 0.85514(18) -0.01313(7) 1.15781(14) 0.0332(3) Uani d . 1 1 H H10 0.7684 0.0226 1.1370 0.040 Uiso calc R 1 1 C C11 0.86494(15) -0.06406(7) 1.05523(12) 0.0262(3) Uani d . 1 1 N N3 0.48970(14) 0.11902(6) 0.81878(11) 0.0290(2) Uani d . 1 1 H H2N 0.5513 0.1028 0.9008 0.035 Uiso calc R 1 1 C C12 0.41601(15) 0.18985(7) 0.81780(12) 0.0255(2) Uani d . 1 1 C C13 0.51258(16) 0.24662(8) 0.89485(13) 0.0303(3) Uani d . 1 1 H H13 0.6266 0.2382 0.9427 0.036 Uiso calc R 1 1 C C14 0.44270(18) 0.31549(8) 0.90199(14) 0.0341(3) Uani d . 1 1 H H14 0.5089 0.3542 0.9551 0.041 Uiso calc R 1 1 C C15 0.27640(18) 0.32813(8) 0.83178(14) 0.0339(3) Uani d . 1 1 H H15 0.2284 0.3754 0.8362 0.041 Uiso calc R 1 1 C C16 0.18101(16) 0.27136(8) 0.75537(14) 0.0323(3) Uani d . 1 1 H H16 0.0671 0.2799 0.7071 0.039 Uiso calc R 1 1 C C17 0.24953(16) 0.20221(7) 0.74832(13) 0.0286(3) Uani d . 1 1 H H17 0.1828 0.1634 0.6961 0.034 Uiso calc R 1 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0426(2) 0.0436(2) 0.02103(15) 0.01742(15) 0.00155(13) -0.00099(13) C1 0.0239(6) 0.0313(6) 0.0248(6) 0.0019(5) 0.0060(5) 0.0000(5) N1 0.0290(5) 0.0306(6) 0.0223(5) 0.0048(4) 0.0029(4) -0.0006(4) N2 0.0277(5) 0.0311(6) 0.0223(5) 0.0017(4) 0.0040(4) 0.0024(4) C2 0.0243(6) 0.0258(6) 0.0246(6) -0.0015(5) 0.0070(5) 0.0022(4) C3 0.0313(6) 0.0284(6) 0.0261(6) -0.0019(5) 0.0066(5) -0.0003(5) C4 0.0397(7) 0.0266(6) 0.0331(7) 0.0021(5) 0.0125(6) -0.0002(5) C5 0.0343(7) 0.0360(7) 0.0395(7) 0.0090(6) 0.0127(6) 0.0045(6) C6 0.0252(6) 0.0289(6) 0.0315(6) -0.0017(5) 0.0082(5) 0.0069(5) C7 0.0254(6) 0.0386(7) 0.0377(7) -0.0014(5) 0.0038(5) 0.0131(6) C8 0.0364(7) 0.0414(8) 0.0292(6) -0.0121(6) -0.0020(5) 0.0101(6) C9 0.0509(9) 0.0318(7) 0.0266(6) -0.0076(6) 0.0037(6) 0.0003(5) C10 0.0405(7) 0.0268(7) 0.0288(6) 0.0009(5) 0.0050(5) 0.0019(5) C11 0.0263(6) 0.0255(6) 0.0254(6) -0.0027(5) 0.0058(5) 0.0044(4) N3 0.0294(5) 0.0337(6) 0.0202(5) 0.0072(4) 0.0019(4) 0.0002(4) C12 0.0263(6) 0.0297(6) 0.0205(5) 0.0030(5) 0.0069(4) 0.0008(4) C13 0.0248(6) 0.0391(7) 0.0242(6) -0.0001(5) 0.0033(5) -0.0019(5) C14 0.0360(7) 0.0323(7) 0.0310(6) -0.0038(5) 0.0057(5) -0.0058(5) C15 0.0383(7) 0.0303(7) 0.0318(7) 0.0055(5) 0.0086(6) -0.0012(5) C16 0.0263(6) 0.0388(7) 0.0292(6) 0.0054(5) 0.0044(5) -0.0012(5) C17 0.0255(6) 0.0323(7) 0.0266(6) -0.0014(5) 0.0058(5) -0.0036(5) 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' 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 N3 C1 N1 114.44(11) N3 C1 S1 125.48(10) N1 C1 S1 120.06(9) C1 N1 N2 117.35(10) C1 N1 H1N 116.9 N2 N1 H1N 121.6 C2 N2 N1 118.38(11) N2 C2 C11 116.45(11) N2 C2 C3 124.48(11) C11 C2 C3 119.01(11) C2 C3 C4 112.33(10) C2 C3 H3A 109.1 C4 C3 H3A 109.1 C2 C3 H3B 109.1 C4 C3 H3B 109.1 H3A C3 H3B 107.9 C5 C4 C3 109.89(11) C5 C4 H4A 109.7 C3 C4 H4A 109.7 C5 C4 H4B 109.7 C3 C4 H4B 109.7 H4A C4 H4B 108.2 C6 C5 C4 110.78(11) C6 C5 H5A 109.5 C4 C5 H5A 109.5 C6 C5 H5B 109.5 C4 C5 H5B 109.5 H5A C5 H5B 108.1 C7 C6 C11 118.80(13) C7 C6 C5 120.80(12) C11 C6 C5 120.40(12) C8 C7 C6 121.45(13) C8 C7 H7 119.3 C6 C7 H7 119.3 C7 C8 C9 119.65(13) C7 C8 H8 120.2 C9 C8 H8 120.2 C8 C9 C10 120.11(14) C8 C9 H9 119.9 C10 C9 H9 119.9 C9 C10 C11 120.61(13) C9 C10 H10 119.7 C11 C10 H10 119.7 C10 C11 C6 119.32(12) C10 C11 C2 120.94(11) C6 C11 C2 119.70(11) C1 N3 C12 127.91(11) C1 N3 H2N 116.0 C12 N3 H2N 116.0 C17 C12 C13 119.87(12) C17 C12 N3 121.61(11) C13 C12 N3 118.44(11) C14 C13 C12 120.06(12) C14 C13 H13 120.0 C12 C13 H13 120.0 C13 C14 C15 120.17(13) C13 C14 H14 119.9 C15 C14 H14 119.9 C16 C15 C14 119.45(13) C16 C15 H15 120.3 C14 C15 H15 120.3 C15 C16 C17 120.79(12) C15 C16 H16 119.6 C17 C16 H16 119.6 C16 C17 C12 119.66(12) C16 C17 H17 120.2 C12 C17 H17 120.2 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C1 1.6773(13) C1 N3 1.3427(16) C1 N1 1.3642(16) N1 N2 1.3846(14) N1 H1N 0.8800 N2 C2 1.2894(16) C2 C11 1.4823(16) C2 C3 1.5055(18) C3 C4 1.5238(18) C3 H3A 0.9900 C3 H3B 0.9900 C4 C5 1.518(2) C4 H4A 0.9900 C4 H4B 0.9900 C5 C6 1.508(2) C5 H5A 0.9900 C5 H5B 0.9900 C6 C7 1.3963(18) C6 C11 1.4033(18) C7 C8 1.380(2) C7 H7 0.9500 C8 C9 1.383(2) C8 H8 0.9500 C9 C10 1.3864(19) C9 H9 0.9500 C10 C11 1.3995(18) C10 H10 0.9500 N3 C12 1.4190(16) N3 H2N 0.8800 C12 C17 1.3861(18) C12 C13 1.3892(18) C13 C14 1.3854(19) C13 H13 0.9500 C14 C15 1.387(2) C14 H14 0.9500 C15 C16 1.3826(19) C15 H15 0.9500 C16 C17 1.3849(19) C16 H16 0.9500 C17 H17 0.9500 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1N S1 3_656 0.88 2.70 3.5793(11) 176.1 N3 H2N N2 . 0.88 2.12 2.5630(15) 110.6 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 N3 C1 N1 N2 -9.03(16) S1 C1 N1 N2 169.57(9) C1 N1 N2 C2 -172.78(11) N1 N2 C2 C11 175.47(10) N1 N2 C2 C3 -1.69(18) N2 C2 C3 C4 -163.68(12) C11 C2 C3 C4 19.23(16) C2 C3 C4 C5 -53.39(15) C3 C4 C5 C6 58.18(15) C4 C5 C6 C7 149.58(12) C4 C5 C6 C11 -29.09(17) C11 C6 C7 C8 0.67(19) C5 C6 C7 C8 -178.02(13) C6 C7 C8 C9 1.4(2) C7 C8 C9 C10 -1.9(2) C8 C9 C10 C11 0.4(2) C9 C10 C11 C6 1.6(2) C9 C10 C11 C2 -175.99(12) C7 C6 C11 C10 -2.16(18) C5 C6 C11 C10 176.54(12) C7 C6 C11 C2 175.51(11) C5 C6 C11 C2 -5.79(18) N2 C2 C11 C10 11.35(18) C3 C2 C11 C10 -171.33(12) N2 C2 C11 C6 -166.29(11) C3 C2 C11 C6 11.04(17) N1 C1 N3 C12 -177.29(12) S1 C1 N3 C12 4.2(2) C1 N3 C12 C17 47.42(19) C1 N3 C12 C13 -135.95(14) C17 C12 C13 C14 -0.13(19) N3 C12 C13 C14 -176.81(12) C12 C13 C14 C15 -0.3(2) C13 C14 C15 C16 0.3(2) C14 C15 C16 C17 0.1(2) C15 C16 C17 C12 -0.5(2) C13 C12 C17 C16 0.51(19) N3 C12 C17 C16 177.09(11)