#------------------------------------------------------------------------------ #$Date: 2019-06-13 03:19:45 +0300 (Thu, 13 Jun 2019) $ #$Revision: 215901 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/13/1551379.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_1551379 loop_ _publ_author_name 'Jiang, Huanfeng' 'He, Dandan' 'Zhuang, Zeyan' 'Wang, Xu' 'Li, Jiawei' 'Li, Jianxiao' 'Wu, Wanqing' 'Zhao, Zujin' 'Tang, Ben Zhong' _publ_section_title ; Assembly of 1H-Isoindole Derivatives by Selective Carbon-Nitrogen Triple Bond Activation: Access to Aggregation-Induced Emission Fluorophores for Lipid Droplets Imaging ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC01035A _journal_year 2019 _chemical_absolute_configuration unk _chemical_formula_moiety 'C18 H17 N3 S' _chemical_formula_sum 'C18 H17 N3 S' _chemical_formula_weight 307.40 _space_group_crystal_system orthorhombic _space_group_IT_number 20 _space_group_name_Hall 'C 2c 2' _space_group_name_H-M_alt 'C 2 2 21' _symmetry_space_group_name_Hall 'C 2c 2' _symmetry_space_group_name_H-M 'C 2 2 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2018-11-18 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2018-11-23 deposited with the CCDC. 2019-06-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 7.306(3) _cell_length_b 18.404(8) _cell_length_c 23.763(9) _cell_measurement_reflns_used 1012 _cell_measurement_temperature 170 _cell_measurement_theta_max 19.038 _cell_measurement_theta_min 2.373 _cell_volume 3195(2) _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 170.0 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_unetI/netI 0.0755 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 11257 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.372 _diffrn_reflns_theta_min 1.714 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.202 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.6751 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0743 before and 0.0601 after correction. The Ratio of minimum to maximum transmission is 0.9057. The \l/2 correction factor is 0.00150.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.278 _exptl_crystal_description block _exptl_crystal_F_000 1296 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.163 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.042 _refine_ls_abs_structure_details ; Flack x determined using 715 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.01(9) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 202 _refine_ls_number_reflns 3269 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.0807 _refine_ls_R_factor_gt 0.0529 _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^)+(0.0402P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1034 _refine_ls_wR_factor_ref 0.1158 _reflns_Friedel_coverage 0.759 _reflns_Friedel_fraction_full 0.998 _reflns_Friedel_fraction_max 0.995 _reflns_number_gt 2327 _reflns_number_total 3269 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; hw-2.res created by SHELXL-2014/7 TITL hw-2_a.res in C222(1) REM Old TITL HW-2 in C222(1) REM SHELXT solution in C222(1) REM R1 0.127, Rweak 0.043, Alpha 0.001, Orientation as input REM Flack x = 0.035 ( 0.088 ) from Parsons' quotients REM Formula found by SHELXT: C18 N3 S CELL 0.71073 7.3059 18.4044 23.7628 90 90 90 ZERR 8 0.0028 0.0081 0.0093 0 0 0 LATT -7 SYMM -X,-Y,0.5+Z SYMM -X,+Y,0.5-Z SYMM +X,-Y,-Z SFAC C H N S UNIT 144 136 24 8 L.S. 4 PLAN 20 0 0 SIZE 0.19 0.16 0.13 TEMP -103.15 BOND $H list 4 fmap 2 acta REM REM REM WGHT 0.040200 FVAR 0.25967 S1 4 0.421890 0.700886 0.550314 11.00000 0.05497 0.05517 = 0.04142 0.00435 0.00605 0.01460 N1 3 0.284822 0.505628 0.677123 11.00000 0.05663 0.02503 = 0.03374 -0.00214 -0.00151 -0.00045 AFIX 43 H1 2 0.278180 0.475808 0.706000 11.00000 -1.20000 AFIX 0 N2 3 0.303938 0.628831 0.651356 11.00000 0.04192 0.03004 = 0.03531 -0.00091 0.00050 0.00026 N3 3 0.266377 0.878785 0.709641 11.00000 0.09609 0.03120 = 0.06301 -0.00295 -0.00248 -0.00073 C1 1 0.138742 0.495698 0.584428 11.00000 0.07041 0.04199 = 0.04830 -0.00602 -0.01494 0.00539 AFIX 137 H1A 2 0.023895 0.486073 0.604389 11.00000 -1.50000 H1B 2 0.139709 0.468887 0.548798 11.00000 -1.50000 H1C 2 0.149231 0.547866 0.576819 11.00000 -1.50000 AFIX 0 C2 1 0.288602 0.389406 0.630648 11.00000 0.07505 0.03051 = 0.04957 -0.00296 -0.00644 -0.00037 AFIX 137 H2A 2 0.394571 0.374014 0.652946 11.00000 -1.50000 H2B 2 0.289024 0.363868 0.594460 11.00000 -1.50000 H2C 2 0.175818 0.377826 0.651092 11.00000 -1.50000 AFIX 0 C3 1 0.298583 0.471375 0.620415 11.00000 0.06213 0.02713 = 0.03511 -0.00625 -0.00521 0.00695 C4 1 0.481312 0.490782 0.593568 11.00000 0.06721 0.04594 = 0.04974 -0.00553 0.01165 0.00478 AFIX 137 H4A 2 0.490897 0.543679 0.589872 11.00000 -1.50000 H4B 2 0.489418 0.468337 0.556253 11.00000 -1.50000 H4C 2 0.581271 0.472824 0.617293 11.00000 -1.50000 AFIX 0 C5 1 0.281486 0.576053 0.688850 11.00000 0.03452 0.02980 = 0.03652 -0.00028 -0.00209 -0.00039 C6 1 0.250051 0.604117 0.746178 11.00000 0.03125 0.03125 = 0.03540 -0.00288 -0.00098 -0.00177 C7 1 0.219824 0.571193 0.797196 11.00000 0.05328 0.03058 = 0.03941 0.00230 -0.00051 -0.00311 AFIX 43 H7 2 0.216199 0.519791 0.800675 11.00000 -1.20000 AFIX 0 C8 1 0.194831 0.616051 0.843385 11.00000 0.05305 0.04894 = 0.03777 -0.00075 0.00405 0.00168 AFIX 43 H8 2 0.173997 0.594651 0.879197 11.00000 -1.20000 AFIX 0 C9 1 0.199199 0.690520 0.839078 11.00000 0.05553 0.04222 = 0.03802 -0.00951 0.00039 0.00002 AFIX 43 H9 2 0.182115 0.719518 0.871731 11.00000 -1.20000 AFIX 0 C10 1 0.228605 0.723915 0.786983 11.00000 0.04839 0.03363 = 0.04262 -0.00676 0.00448 -0.00006 AFIX 43 H10 2 0.231124 0.775345 0.783663 11.00000 -1.20000 AFIX 0 C11 1 0.253736 0.680221 0.740764 11.00000 0.02914 0.02751 = 0.03758 -0.00391 -0.00079 0.00034 C12 1 0.288891 0.693656 0.680322 11.00000 0.03206 0.03113 = 0.03969 0.00021 -0.00038 -0.00034 C13 1 0.304170 0.759298 0.653654 11.00000 0.03471 0.03058 = 0.04265 -0.00359 -0.00405 -0.00162 C14 1 0.283287 0.824755 0.685115 11.00000 0.05511 0.03242 = 0.04220 0.00251 -0.00534 -0.00654 C15 1 0.346970 0.770001 0.594232 11.00000 0.03349 0.03570 = 0.04132 0.00279 -0.00479 -0.00381 C16 1 0.345074 0.833931 0.565474 11.00000 0.06130 0.03555 = 0.05023 0.00605 -0.00965 -0.00738 AFIX 43 H16 2 0.307237 0.878482 0.581978 11.00000 -1.20000 AFIX 0 C17 1 0.403310 0.828569 0.509764 11.00000 0.06634 0.05824 = 0.05315 0.02386 -0.00361 -0.01422 AFIX 43 H17 2 0.409700 0.868582 0.484584 11.00000 -1.20000 AFIX 0 C18 1 0.449342 0.760229 0.495832 11.00000 0.05021 0.07575 = 0.04265 0.01263 0.00443 0.00535 AFIX 43 H18 2 0.492410 0.746478 0.459645 11.00000 -1.20000 AFIX 0 HKLF 4 REM hw-2_a.res in C222(1) REM R1 = 0.0529 for 2327 Fo > 4sig(Fo) and 0.0807 for all 3269 data REM 202 parameters refined using 0 restraints END WGHT 0.0401 0.0000 REM Highest difference peak 0.163, deepest hole -0.206, 1-sigma level 0.042 Q1 1 0.5169 0.9221 0.4687 11.00000 0.05 0.16 Q2 1 0.5035 0.4384 0.7125 11.00000 0.05 0.15 Q3 1 0.5781 0.7483 0.3889 11.00000 0.05 0.15 Q4 1 0.4929 0.5711 0.7133 11.00000 0.05 0.15 Q5 1 0.4628 0.6988 0.7348 11.00000 0.05 0.15 Q6 1 0.1828 0.7980 0.8130 11.00000 0.05 0.14 Q7 1 0.3001 0.6528 0.9246 11.00000 0.05 0.14 Q8 1 0.5000 0.8531 0.7500 10.50000 0.05 0.14 Q9 1 0.5311 0.6554 0.5168 11.00000 0.05 0.14 Q10 1 0.4253 0.6982 0.7831 11.00000 0.05 0.14 Q11 1 -0.0292 0.7594 0.8207 11.00000 0.05 0.14 Q12 1 0.5268 0.6727 0.4390 11.00000 0.05 0.14 Q13 1 0.2019 0.8254 0.4998 11.00000 0.05 0.13 Q14 1 0.6893 0.7915 0.4811 11.00000 0.05 0.13 Q15 1 0.1586 0.3027 0.5433 11.00000 0.05 0.13 Q16 1 0.4364 0.8274 0.5439 11.00000 0.05 0.13 Q17 1 -0.0105 0.6852 0.8279 11.00000 0.05 0.13 Q18 1 0.6098 0.7620 0.4675 11.00000 0.05 0.13 Q19 1 0.4375 0.8015 0.7971 11.00000 0.05 0.13 Q20 1 0.2348 0.5481 0.7264 11.00000 0.05 0.12 REM The information below was added by Olex2. REM REM R1 = 0.0529 for 2327 Fo > 4sig(Fo) and 0.0807 for all 11299 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.16, deepest hole -0.21 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0807 REM R1_gt = 0.0529 REM wR_ref = 0.1158 REM GOOF = 1.041 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 11299 REM Reflections_gt = 2327 REM Parameters = n/a REM Hole = -0.21 REM Peak = 0.16 REM Flack = 0.01(9) ; _cod_data_source_file c9sc01035a2.cif _cod_data_source_block hw-2 _cod_database_code 1551379 _shelx_shelxl_version_number 2014/7 _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 0.974 _shelx_estimated_absorpt_t_min 0.963 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: N1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17), C18(H18) 2.b Idealised Me refined as rotating group: C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C4(H4A,H4B,H4C) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 S1 S 0.42189(17) 0.70089(7) 0.55031(5) 0.0505(4) Uani 1 1 d . N1 N 0.2848(5) 0.50563(18) 0.67712(13) 0.0385(9) Uani 1 1 d . H1 H 0.2782 0.4758 0.7060 0.046 Uiso 1 1 calc R N2 N 0.3039(5) 0.62883(18) 0.65136(13) 0.0358(8) Uani 1 1 d . N3 N 0.2664(7) 0.8788(2) 0.70964(18) 0.0634(12) Uani 1 1 d . C1 C 0.1387(7) 0.4957(3) 0.58443(19) 0.0536(13) Uani 1 1 d . H1A H 0.0239 0.4861 0.6044 0.080 Uiso 1 1 calc GR H1B H 0.1397 0.4689 0.5488 0.080 Uiso 1 1 calc GR H1C H 0.1492 0.5479 0.5768 0.080 Uiso 1 1 calc GR C2 C 0.2886(8) 0.3894(2) 0.63065(19) 0.0517(13) Uani 1 1 d . H2A H 0.3946 0.3740 0.6529 0.078 Uiso 1 1 calc GR H2B H 0.2890 0.3639 0.5945 0.078 Uiso 1 1 calc GR H2C H 0.1758 0.3778 0.6511 0.078 Uiso 1 1 calc GR C3 C 0.2986(7) 0.4714(2) 0.62042(17) 0.0415(11) Uani 1 1 d . C4 C 0.4813(7) 0.4908(3) 0.5936(2) 0.0543(13) Uani 1 1 d . H4A H 0.4909 0.5437 0.5899 0.081 Uiso 1 1 calc GR H4B H 0.4894 0.4683 0.5563 0.081 Uiso 1 1 calc GR H4C H 0.5813 0.4728 0.6173 0.081 Uiso 1 1 calc GR C5 C 0.2815(6) 0.5761(2) 0.68885(16) 0.0336(9) Uani 1 1 d . C6 C 0.2501(6) 0.6041(2) 0.74618(17) 0.0326(9) Uani 1 1 d . C7 C 0.2198(6) 0.5712(2) 0.79720(17) 0.0411(11) Uani 1 1 d . H7 H 0.2162 0.5198 0.8007 0.049 Uiso 1 1 calc R C8 C 0.1948(7) 0.6161(2) 0.84338(19) 0.0466(12) Uani 1 1 d . H8 H 0.1740 0.5947 0.8792 0.056 Uiso 1 1 calc R C9 C 0.1992(6) 0.6905(3) 0.83908(18) 0.0453(11) Uani 1 1 d . H9 H 0.1821 0.7195 0.8717 0.054 Uiso 1 1 calc R C10 C 0.2286(6) 0.7239(2) 0.78698(18) 0.0415(11) Uani 1 1 d . H10 H 0.2311 0.7753 0.7837 0.050 Uiso 1 1 calc R C11 C 0.2537(5) 0.6802(2) 0.74076(16) 0.0314(9) Uani 1 1 d . C12 C 0.2889(6) 0.6937(2) 0.68032(16) 0.0343(9) Uani 1 1 d . C13 C 0.3042(6) 0.7593(2) 0.65365(17) 0.0360(10) Uani 1 1 d . C14 C 0.2833(7) 0.8248(2) 0.68511(18) 0.0432(11) Uani 1 1 d . C15 C 0.3470(6) 0.7700(2) 0.59423(18) 0.0368(10) Uani 1 1 d . C16 C 0.3451(7) 0.8339(3) 0.56547(19) 0.0490(13) Uani 1 1 d . H16 H 0.3072 0.8785 0.5820 0.059 Uiso 1 1 calc R C17 C 0.4033(7) 0.8286(3) 0.5098(2) 0.0592(15) Uani 1 1 d . H17 H 0.4097 0.8686 0.4846 0.071 Uiso 1 1 calc R C18 C 0.4493(7) 0.7602(3) 0.4958(2) 0.0562(14) Uani 1 1 d . H18 H 0.4924 0.7465 0.4596 0.067 Uiso 1 1 calc R 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 0.0550(7) 0.0552(8) 0.0414(6) 0.0044(6) 0.0061(6) 0.0146(7) N1 0.057(2) 0.0250(19) 0.0337(18) -0.0021(14) -0.0015(19) -0.0004(19) N2 0.042(2) 0.030(2) 0.0353(18) -0.0009(15) 0.0005(17) 0.0003(18) N3 0.096(4) 0.031(2) 0.063(3) -0.003(2) -0.002(3) -0.001(3) C1 0.070(3) 0.042(3) 0.048(3) -0.006(2) -0.015(3) 0.005(3) C2 0.075(4) 0.031(3) 0.050(3) -0.003(2) -0.006(3) 0.000(3) C3 0.062(3) 0.027(2) 0.035(2) -0.0063(18) -0.005(2) 0.007(2) C4 0.067(3) 0.046(3) 0.050(3) -0.006(2) 0.012(3) 0.005(3) C5 0.035(2) 0.030(2) 0.037(2) -0.0003(18) -0.002(2) 0.000(2) C6 0.031(2) 0.031(2) 0.035(2) -0.0029(18) -0.0010(17) -0.002(2) C7 0.053(3) 0.031(2) 0.039(2) 0.0023(19) -0.001(2) -0.003(2) C8 0.053(3) 0.049(3) 0.038(2) -0.001(2) 0.004(2) 0.002(3) C9 0.056(3) 0.042(3) 0.038(2) -0.010(2) 0.000(2) 0.000(3) C10 0.048(3) 0.034(2) 0.043(2) -0.0068(19) 0.004(2) 0.000(2) C11 0.029(2) 0.028(2) 0.038(2) -0.0039(17) -0.0008(17) 0.0003(19) C12 0.032(2) 0.031(2) 0.040(2) 0.000(2) -0.0004(19) 0.000(2) C13 0.035(2) 0.031(2) 0.043(2) -0.0036(19) -0.004(2) -0.002(2) C14 0.055(3) 0.032(3) 0.042(2) 0.003(2) -0.005(2) -0.007(2) C15 0.033(2) 0.036(3) 0.041(2) 0.003(2) -0.005(2) -0.004(2) C16 0.061(3) 0.036(3) 0.050(3) 0.006(2) -0.010(2) -0.007(2) C17 0.066(4) 0.058(4) 0.053(3) 0.024(3) -0.004(3) -0.014(3) C18 0.050(3) 0.076(4) 0.043(3) 0.013(3) 0.004(3) 0.005(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' 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 C18 S1 C15 91.4(3) C3 N1 H1 116.4 C5 N1 H1 116.4 C5 N1 C3 127.2(3) C5 N2 C12 106.7(3) H1A C1 H1B 109.5 H1A C1 H1C 109.5 H1B C1 H1C 109.5 C3 C1 H1A 109.5 C3 C1 H1B 109.5 C3 C1 H1C 109.5 H2A C2 H2B 109.5 H2A C2 H2C 109.5 H2B C2 H2C 109.5 C3 C2 H2A 109.5 C3 C2 H2B 109.5 C3 C2 H2C 109.5 N1 C3 C1 109.5(4) N1 C3 C2 105.7(3) N1 C3 C4 109.8(4) C1 C3 C2 110.1(4) C1 C3 C4 111.7(4) C4 C3 C2 109.9(4) C3 C4 H4A 109.5 C3 C4 H4B 109.5 C3 C4 H4C 109.5 H4A C4 H4B 109.5 H4A C4 H4C 109.5 H4B C4 H4C 109.5 N1 C5 N2 124.9(3) N1 C5 C6 122.6(4) N2 C5 C6 112.5(4) C7 C6 C5 133.3(4) C7 C6 C11 121.5(4) C11 C6 C5 105.1(3) C6 C7 H7 121.4 C6 C7 C8 117.2(4) C8 C7 H7 121.4 C7 C8 H8 118.9 C9 C8 C7 122.1(4) C9 C8 H8 118.9 C8 C9 H9 119.7 C8 C9 C10 120.5(4) C10 C9 H9 119.7 C9 C10 H10 121.0 C11 C10 C9 118.1(4) C11 C10 H10 121.0 C6 C11 C12 105.0(3) C10 C11 C6 120.5(4) C10 C11 C12 134.5(4) N2 C12 C11 110.7(3) C13 C12 N2 121.7(3) C13 C12 C11 127.7(4) C12 C13 C14 119.6(4) C12 C13 C15 125.8(4) C14 C13 C15 114.6(4) N3 C14 C13 178.6(5) C13 C15 S1 123.4(3) C16 C15 S1 109.6(3) C16 C15 C13 126.9(4) C15 C16 H16 122.8 C15 C16 C17 114.4(5) C17 C16 H16 122.8 C16 C17 H17 123.9 C18 C17 C16 112.1(5) C18 C17 H17 123.9 S1 C18 H18 123.7 C17 C18 S1 112.5(4) C17 C18 H18 123.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C15 1.734(4) S1 C18 1.706(5) N1 H1 0.8800 N1 C3 1.491(5) N1 C5 1.326(5) N2 C5 1.328(5) N2 C12 1.382(5) N3 C14 1.159(6) C1 H1A 0.9800 C1 H1B 0.9800 C1 H1C 0.9800 C1 C3 1.515(6) C2 H2A 0.9800 C2 H2B 0.9800 C2 H2C 0.9800 C2 C3 1.530(6) C3 C4 1.522(7) C4 H4A 0.9800 C4 H4B 0.9800 C4 H4C 0.9800 C5 C6 1.475(6) C6 C7 1.373(6) C6 C11 1.407(5) C7 H7 0.9500 C7 C8 1.386(6) C8 H8 0.9500 C8 C9 1.375(6) C9 H9 0.9500 C9 C10 1.399(6) C10 H10 0.9500 C10 C11 1.374(5) C11 C12 1.480(5) C12 C13 1.369(6) C13 C14 1.426(6) C13 C15 1.460(6) C15 C16 1.361(6) C16 H16 0.9500 C16 C17 1.394(7) C17 H17 0.9500 C17 C18 1.343(7) C18 H18 0.9500