#------------------------------------------------------------------------------ #$Date: 2026-06-05 20:28:11 +0100 (Fri, 05 Jun 2026) $ #$Revision: 306470 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064391.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_7064391 loop_ _publ_author_name 'Liu, Shuai' 'Liu, Yu-Tao' 'Liu, Jiahui' 'Chen, Zihao' 'Ding, Yue' 'Wu, Qiong' 'Zhang, Tian-Shu' 'Ding, Weijie' _publ_section_title ; H2O-controlled selective disulfide etherification and thiocyanation of pyrroles via linear paired electrolysis ; _journal_issue 20 _journal_name_full 'New Journal of Chemistry' _journal_page_first 8727 _journal_page_last 8732 _journal_paper_doi 10.1039/D6NJ00883F _journal_volume 50 _journal_year 2026 _chemical_formula_moiety 'C18 H24 N2 O4 S2' _chemical_formula_sum 'C18 H24 N2 O4 S2' _chemical_formula_weight 396.51 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2025-08-11 _audit_creation_method ; Olex2 1.5 (compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928) ; _audit_update_record ; 2025-11-24 deposited with the CCDC. 2026-04-29 downloaded from the CCDC. ; _cell_angle_alpha 78.905(4) _cell_angle_beta 85.544(4) _cell_angle_gamma 85.215(4) _cell_formula_units_Z 2 _cell_length_a 8.5875(10) _cell_length_b 10.6673(10) _cell_length_c 11.4787(14) _cell_measurement_reflns_used 9971 _cell_measurement_temperature 302.00 _cell_measurement_theta_max 28.140 _cell_measurement_theta_min 2.385 _cell_volume 1026.2(2) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2014/7 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 302.00 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _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 0.0553 _diffrn_reflns_av_unetI/netI 0.0289 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 42967 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.290 _diffrn_reflns_theta_min 1.950 _diffrn_source_current 1.4 _diffrn_source_power 0.07 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 0.284 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.7044 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1044 before and 0.0552 after correction. The Ratio of minimum to maximum transmission is 0.9446. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.283 _exptl_crystal_description block _exptl_crystal_F_000 420 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.21 _refine_diff_density_max 0.273 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.040 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 241 _refine_ls_number_reflns 5090 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.074 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0400 _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^)+(0.0658P)^2^+0.1467P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1145 _refine_ls_wR_factor_ref 0.1223 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4202 _reflns_number_total 5090 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6nj00883f2.cif _cod_data_source_block mo_li3030 _cod_depositor_comments 'Adding full bibliography for 7064391.cif.' _cod_database_code 7064391 _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 0.943 _shelx_estimated_absorpt_t_min 0.912 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C17(H17A,H17B) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C11(H11) 2.c Idealised Me refined as rotating group: C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C18(H18A,H18B,H18C) ; _shelx_res_file ; mo_li3030.res created by SHELXL-2014/7 TITL mo_li3030_a.res in P-1 REM Old TITL mo_Li3030 in P-1 REM SHELXT solution in P-1 REM R1 0.162, Rweak 0.010, Alpha 0.041, Orientation as input REM Formula found by SHELXT: C18 N3 O3 S2 CELL 0.71073 8.5875 10.6673 11.4787 78.905 85.544 85.215 ZERR 2 0.001 0.001 0.0014 0.004 0.004 0.004 LATT 1 SFAC C H N O S UNIT 36 48 4 8 4 L.S. 4 0 0 PLAN 5 SIZE 0.33 0.23 0.21 TEMP 28.85 CONF BOND $H list 4 fmap 2 53 MORE -1 ACTA REM REM REM WGHT 0.065800 0.146700 FVAR 1.35103 S1 5 0.116098 0.944442 0.705009 11.00000 0.06042 0.04963 = 0.04560 -0.00517 -0.00506 0.01460 S2 5 -0.014784 0.784271 0.740632 11.00000 0.04482 0.07472 = 0.04811 -0.00540 -0.00965 0.00229 O1 4 0.332204 0.896233 0.246184 11.00000 0.06747 0.07854 = 0.04651 -0.01303 0.00515 -0.00024 O2 4 0.563786 0.789611 0.284226 11.00000 0.08571 0.12725 = 0.08531 -0.03669 0.00808 0.03706 O3 4 0.112600 0.612143 1.213845 11.00000 0.06498 0.06280 = 0.04504 -0.00486 -0.00363 0.01101 O4 4 0.302539 0.461192 1.191958 11.00000 0.08652 0.08134 = 0.06358 0.00143 -0.00991 0.03564 N1 3 0.492064 0.819482 0.535563 11.00000 0.04119 0.04593 = 0.06545 -0.00681 -0.00782 0.00415 N2 3 0.243982 0.516242 0.935421 11.00000 0.04325 0.04169 = 0.05758 -0.01092 0.00195 0.00035 C1 1 0.266353 0.901863 0.605323 11.00000 0.04593 0.04090 = 0.04604 -0.00266 -0.00736 0.00529 C2 1 0.258573 0.910467 0.482606 11.00000 0.04430 0.04609 = 0.04764 -0.00356 -0.00599 0.00368 AFIX 43 H2 2 0.174065 0.944888 0.437970 11.00000 -1.20000 AFIX 0 C3 1 0.398557 0.858784 0.440155 11.00000 0.04648 0.04565 = 0.05368 -0.00580 -0.00268 0.00052 C4 1 0.413096 0.845510 0.636034 11.00000 0.04753 0.03920 = 0.05733 -0.00377 -0.01310 0.00239 C5 1 0.651268 0.758989 0.531225 11.00000 0.04628 0.07120 = 0.09463 -0.01054 -0.00817 0.01460 AFIX 137 H5A 2 0.648763 0.675504 0.512024 11.00000 -1.50000 H5B 2 0.694176 0.751180 0.607273 11.00000 -1.50000 H5C 2 0.715277 0.810608 0.471532 11.00000 -1.50000 AFIX 0 C6 1 0.480578 0.815970 0.755115 11.00000 0.06598 0.06198 = 0.06851 -0.00673 -0.03049 0.00706 AFIX 137 H6A 2 0.499467 0.724967 0.778796 11.00000 -1.50000 H6B 2 0.408241 0.847859 0.812417 11.00000 -1.50000 H6C 2 0.577404 0.856096 0.750680 11.00000 -1.50000 AFIX 0 C7 1 0.444359 0.842945 0.318394 11.00000 0.05887 0.05552 = 0.06229 -0.01367 0.00564 -0.00104 C8 1 0.356487 0.887249 0.121680 11.00000 0.09090 0.08504 = 0.05058 -0.02033 0.01220 -0.00910 AFIX 23 H8A 2 0.351143 0.799393 0.111986 11.00000 -1.20000 H8B 2 0.458575 0.915356 0.090401 11.00000 -1.20000 AFIX 0 C9 1 0.231931 0.970295 0.058127 11.00000 0.11878 0.12564 = 0.05649 -0.02970 -0.01253 0.01043 AFIX 137 H9A 2 0.242334 0.964150 -0.024499 11.00000 -1.50000 H9B 2 0.240887 1.057394 0.065836 11.00000 -1.50000 H9C 2 0.131503 0.943394 0.091680 11.00000 -1.50000 AFIX 0 C10 1 0.087178 0.677651 0.848536 11.00000 0.04170 0.05036 = 0.04714 -0.00788 -0.00260 -0.00232 C11 1 0.074836 0.676608 0.971398 11.00000 0.04161 0.04502 = 0.04678 -0.00632 0.00102 0.00127 AFIX 43 H11 2 0.012026 0.733317 1.010009 11.00000 -1.20000 AFIX 0 C12 1 0.172370 0.576624 1.024262 11.00000 0.04208 0.04201 = 0.04884 -0.00490 0.00091 -0.00116 C13 1 0.193848 0.577200 0.828816 11.00000 0.04388 0.05094 = 0.05333 -0.01490 0.00122 -0.00662 C14 1 0.345841 0.397625 0.952771 11.00000 0.06283 0.04921 = 0.08558 -0.01762 -0.00133 0.01304 AFIX 137 H14A 2 0.449503 0.416538 0.966437 11.00000 -1.50000 H14B 2 0.349388 0.359905 0.883041 11.00000 -1.50000 H14C 2 0.305302 0.338794 1.020190 11.00000 -1.50000 AFIX 0 C15 1 0.253504 0.538146 0.714687 11.00000 0.07070 0.07562 = 0.06380 -0.03143 0.00225 -0.00206 AFIX 137 H15A 2 0.364982 0.543228 0.704929 11.00000 -1.50000 H15B 2 0.205261 0.594284 0.649687 11.00000 -1.50000 H15C 2 0.228684 0.451778 0.715950 11.00000 -1.50000 AFIX 0 C16 1 0.204814 0.540747 1.148905 11.00000 0.04849 0.04589 = 0.05243 0.00044 -0.00008 0.00044 C17 1 0.138492 0.593743 1.339409 11.00000 0.07922 0.07358 = 0.04419 -0.00079 -0.00218 -0.00077 AFIX 23 H17A 2 0.245186 0.610447 1.350381 11.00000 -1.20000 H17B 2 0.120890 0.506418 1.377970 11.00000 -1.20000 AFIX 0 C18 1 0.026922 0.684342 1.390454 11.00000 0.08279 0.08879 = 0.06321 -0.02698 0.00080 -0.00933 AFIX 137 H18A 2 0.042654 0.770038 1.349294 11.00000 -1.50000 H18B 2 0.043572 0.677563 1.473238 11.00000 -1.50000 H18C 2 -0.078144 0.664446 1.382083 11.00000 -1.50000 AFIX 0 HKLF 4 REM mo_li3030_a.res in P-1 REM R1 = 0.0400 for 4202 Fo > 4sig(Fo) and 0.0480 for all 5090 data REM 241 parameters refined using 0 restraints END WGHT 0.0658 0.1467 REM Highest difference peak 0.273, deepest hole -0.200, 1-sigma level 0.040 Q1 1 0.3361 0.8855 0.6251 11.00000 0.05 0.27 Q2 1 0.0860 0.6934 0.9015 11.00000 0.05 0.25 Q3 1 0.1356 0.6256 0.8318 11.00000 0.05 0.23 Q4 1 0.2766 0.4674 0.9441 11.00000 0.05 0.22 Q5 1 0.4185 0.8660 0.3827 11.00000 0.05 0.21 ; _shelx_res_checksum 37279 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.11610(5) 0.94444(4) 0.70501(3) 0.05335(13) Uani 1 1 d . . . . . S2 S -0.01478(4) 0.78427(4) 0.74063(4) 0.05671(13) Uani 1 1 d . . . . . O1 O 0.33220(15) 0.89623(12) 0.24618(10) 0.0647(3) Uani 1 1 d . . . . . O2 O 0.5638(2) 0.78961(18) 0.28423(15) 0.1004(5) Uani 1 1 d . . . . . O3 O 0.11260(14) 0.61214(11) 1.21384(9) 0.0592(3) Uani 1 1 d . . . . . O4 O 0.30254(18) 0.46119(14) 1.19196(12) 0.0812(4) Uani 1 1 d . . . . . N1 N 0.49206(14) 0.81948(12) 0.53556(12) 0.0515(3) Uani 1 1 d . . . . . N2 N 0.24398(14) 0.51624(11) 0.93542(12) 0.0478(3) Uani 1 1 d . . . . . C1 C 0.26635(17) 0.90186(13) 0.60532(13) 0.0453(3) Uani 1 1 d . . . . . C2 C 0.25857(17) 0.91047(13) 0.48261(13) 0.0469(3) Uani 1 1 d . . . . . H2 H 0.1741 0.9449 0.4380 0.056 Uiso 1 1 calc R U . . . C3 C 0.39856(17) 0.85878(14) 0.44015(14) 0.0493(3) Uani 1 1 d . . . . . C4 C 0.41310(17) 0.84551(13) 0.63603(14) 0.0485(3) Uani 1 1 d . . . . . C5 C 0.6513(2) 0.75899(19) 0.5312(2) 0.0722(5) Uani 1 1 d . . . . . H5A H 0.6488 0.6755 0.5120 0.108 Uiso 1 1 calc R U . . . H5B H 0.6942 0.7512 0.6073 0.108 Uiso 1 1 calc R U . . . H5C H 0.7153 0.8106 0.4715 0.108 Uiso 1 1 calc R U . . . C6 C 0.4806(2) 0.81597(17) 0.75512(17) 0.0655(5) Uani 1 1 d . . . . . H6A H 0.4995 0.7250 0.7788 0.098 Uiso 1 1 calc R U . . . H6B H 0.4082 0.8479 0.8124 0.098 Uiso 1 1 calc R U . . . H6C H 0.5774 0.8561 0.7507 0.098 Uiso 1 1 calc R U . . . C7 C 0.4444(2) 0.84295(16) 0.31839(16) 0.0592(4) Uani 1 1 d . . . . . C8 C 0.3565(3) 0.8872(2) 0.12168(16) 0.0752(5) Uani 1 1 d . . . . . H8A H 0.3511 0.7994 0.1120 0.090 Uiso 1 1 calc R U . . . H8B H 0.4586 0.9154 0.0904 0.090 Uiso 1 1 calc R U . . . C9 C 0.2319(3) 0.9703(3) 0.0581(2) 0.0993(8) Uani 1 1 d . . . . . H9A H 0.2423 0.9642 -0.0245 0.149 Uiso 1 1 calc R U . . . H9B H 0.2409 1.0574 0.0658 0.149 Uiso 1 1 calc R U . . . H9C H 0.1315 0.9434 0.0917 0.149 Uiso 1 1 calc R U . . . C10 C 0.08718(16) 0.67765(14) 0.84854(13) 0.0466(3) Uani 1 1 d . . . . . C11 C 0.07484(16) 0.67661(13) 0.97140(13) 0.0452(3) Uani 1 1 d . . . . . H11 H 0.0120 0.7333 1.0100 0.054 Uiso 1 1 calc R U . . . C12 C 0.17237(16) 0.57662(13) 1.02426(13) 0.0451(3) Uani 1 1 d . . . . . C13 C 0.19385(17) 0.57720(14) 0.82882(14) 0.0487(3) Uani 1 1 d . . . . . C14 C 0.3458(2) 0.39762(16) 0.95277(19) 0.0664(5) Uani 1 1 d . . . . . H14A H 0.4495 0.4165 0.9664 0.100 Uiso 1 1 calc R U . . . H14B H 0.3494 0.3599 0.8830 0.100 Uiso 1 1 calc R U . . . H14C H 0.3053 0.3388 1.0202 0.100 Uiso 1 1 calc R U . . . C15 C 0.2535(2) 0.53815(19) 0.71469(17) 0.0681(5) Uani 1 1 d . . . . . H15A H 0.3650 0.5432 0.7049 0.102 Uiso 1 1 calc R U . . . H15B H 0.2053 0.5943 0.6497 0.102 Uiso 1 1 calc R U . . . H15C H 0.2287 0.4518 0.7160 0.102 Uiso 1 1 calc R U . . . C16 C 0.20481(18) 0.54075(14) 1.14890(14) 0.0506(3) Uani 1 1 d . . . . . C17 C 0.1385(2) 0.59374(19) 1.33941(15) 0.0674(5) Uani 1 1 d . . . . . H17A H 0.2452 0.6104 1.3504 0.081 Uiso 1 1 calc R U . . . H17B H 0.1209 0.5064 1.3780 0.081 Uiso 1 1 calc R U . . . C18 C 0.0269(3) 0.6843(2) 1.39045(19) 0.0767(5) Uani 1 1 d . . . . . H18A H 0.0427 0.7700 1.3493 0.115 Uiso 1 1 calc R U . . . H18B H 0.0436 0.6776 1.4732 0.115 Uiso 1 1 calc R U . . . H18C H -0.0781 0.6644 1.3821 0.115 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 S1 0.0604(2) 0.0496(2) 0.0456(2) -0.00517(15) -0.00506(16) 0.01460(16) S2 0.0448(2) 0.0747(3) 0.0481(2) -0.00540(17) -0.00965(15) 0.00229(17) O1 0.0675(7) 0.0785(8) 0.0465(6) -0.0130(5) 0.0052(5) -0.0002(6) O2 0.0857(11) 0.1272(14) 0.0853(11) -0.0367(10) 0.0081(8) 0.0371(10) O3 0.0650(7) 0.0628(7) 0.0450(6) -0.0049(5) -0.0036(5) 0.0110(5) O4 0.0865(10) 0.0813(9) 0.0636(8) 0.0014(6) -0.0099(7) 0.0356(7) N1 0.0412(6) 0.0459(6) 0.0655(8) -0.0068(5) -0.0078(5) 0.0041(5) N2 0.0433(6) 0.0417(6) 0.0576(7) -0.0109(5) 0.0020(5) 0.0004(5) C1 0.0459(7) 0.0409(6) 0.0460(7) -0.0027(5) -0.0074(6) 0.0053(5) C2 0.0443(7) 0.0461(7) 0.0476(7) -0.0036(5) -0.0060(6) 0.0037(5) C3 0.0465(7) 0.0456(7) 0.0537(8) -0.0058(6) -0.0027(6) 0.0005(6) C4 0.0475(7) 0.0392(6) 0.0573(8) -0.0038(6) -0.0131(6) 0.0024(5) C5 0.0463(9) 0.0712(11) 0.0946(14) -0.0105(10) -0.0082(9) 0.0146(8) C6 0.0660(10) 0.0620(9) 0.0685(11) -0.0067(8) -0.0305(9) 0.0071(8) C7 0.0589(9) 0.0555(9) 0.0623(10) -0.0137(7) 0.0056(7) -0.0010(7) C8 0.0909(14) 0.0850(13) 0.0506(9) -0.0203(9) 0.0122(9) -0.0091(10) C9 0.119(2) 0.126(2) 0.0565(12) -0.0297(13) -0.0125(12) 0.0104(16) C10 0.0417(7) 0.0504(7) 0.0471(7) -0.0079(6) -0.0026(6) -0.0023(5) C11 0.0416(7) 0.0450(7) 0.0468(7) -0.0063(5) 0.0010(5) 0.0013(5) C12 0.0421(7) 0.0420(6) 0.0488(7) -0.0049(5) 0.0009(6) -0.0012(5) C13 0.0439(7) 0.0509(7) 0.0533(8) -0.0149(6) 0.0012(6) -0.0066(6) C14 0.0628(10) 0.0492(8) 0.0856(12) -0.0176(8) -0.0013(9) 0.0130(7) C15 0.0707(11) 0.0756(11) 0.0638(10) -0.0314(9) 0.0023(9) -0.0021(9) C16 0.0485(8) 0.0459(7) 0.0524(8) 0.0004(6) -0.0001(6) 0.0004(6) C17 0.0792(12) 0.0736(11) 0.0442(8) -0.0008(7) -0.0022(8) -0.0008(9) C18 0.0828(13) 0.0888(13) 0.0632(11) -0.0270(10) 0.0008(9) -0.0093(10) 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' 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 S2 102.74(5) . . ? C10 S2 S1 103.85(5) . . ? C7 O1 C8 117.66(15) . . ? C16 O3 C17 117.12(13) . . ? C3 N1 C5 126.37(15) . . ? C4 N1 C3 109.39(12) . . ? C4 N1 C5 124.24(15) . . ? C12 N2 C14 126.23(14) . . ? C13 N2 C12 109.29(12) . . ? C13 N2 C14 124.22(14) . . ? C2 C1 S1 126.75(11) . . ? C4 C1 S1 125.40(12) . . ? C4 C1 C2 107.74(13) . . ? C1 C2 H2 126.2 . . ? C3 C2 C1 107.53(13) . . ? C3 C2 H2 126.2 . . ? N1 C3 C7 124.46(14) . . ? C2 C3 N1 107.68(13) . . ? C2 C3 C7 127.84(15) . . ? N1 C4 C1 107.66(13) . . ? N1 C4 C6 123.26(14) . . ? C1 C4 C6 129.08(15) . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5B 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6B 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O1 C7 C3 110.04(14) . . ? O2 C7 O1 123.07(17) . . ? O2 C7 C3 126.88(18) . . ? O1 C8 H8A 110.3 . . ? O1 C8 H8B 110.3 . . ? O1 C8 C9 107.30(17) . . ? H8A C8 H8B 108.5 . . ? C9 C8 H8A 110.3 . . ? C9 C8 H8B 110.3 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 S2 126.23(11) . . ? C13 C10 S2 126.37(12) . . ? C13 C10 C11 107.39(13) . . ? C10 C11 H11 126.2 . . ? C12 C11 C10 107.61(13) . . ? C12 C11 H11 126.2 . . ? N2 C12 C16 124.24(13) . . ? C11 C12 N2 107.73(13) . . ? C11 C12 C16 127.96(13) . . ? N2 C13 C10 107.97(13) . . ? N2 C13 C15 122.46(14) . . ? C10 C13 C15 129.55(15) . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 C12 110.52(12) . . ? O4 C16 O3 122.42(15) . . ? O4 C16 C12 127.03(15) . . ? O3 C17 H17A 110.3 . . ? O3 C17 H17B 110.3 . . ? O3 C17 C18 107.00(16) . . ? H17A C17 H17B 108.6 . . ? C18 C17 H17A 110.3 . . ? C18 C17 H17B 110.3 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 S1 S2 2.0808(6) . ? S1 C1 1.7474(15) . ? S2 C10 1.7477(15) . ? O1 C7 1.338(2) . ? O1 C8 1.449(2) . ? O2 C7 1.206(2) . ? O3 C16 1.3375(19) . ? O3 C17 1.449(2) . ? O4 C16 1.2054(18) . ? N1 C3 1.3870(19) . ? N1 C4 1.355(2) . ? N1 C5 1.464(2) . ? N2 C12 1.3865(19) . ? N2 C13 1.354(2) . ? N2 C14 1.4667(18) . ? C1 C2 1.400(2) . ? C1 C4 1.3909(19) . ? C2 H2 0.9300 . ? C2 C3 1.374(2) . ? C3 C7 1.460(2) . ? C4 C6 1.493(2) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 C9 1.475(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.404(2) . ? C10 C13 1.391(2) . ? C11 H11 0.9300 . ? C11 C12 1.3741(19) . ? C12 C16 1.451(2) . ? C13 C15 1.491(2) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 C18 1.474(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S1 S2 C10 C11 83.14(13) . . . . ? S1 S2 C10 C13 -97.79(13) . . . . ? S1 C1 C2 C3 -175.82(11) . . . . ? S1 C1 C4 N1 175.93(11) . . . . ? S1 C1 C4 C6 -4.2(2) . . . . ? S2 S1 C1 C2 81.95(13) . . . . ? S2 S1 C1 C4 -93.80(13) . . . . ? S2 C10 C11 C12 179.01(11) . . . . ? S2 C10 C13 N2 -178.72(10) . . . . ? S2 C10 C13 C15 3.0(2) . . . . ? N1 C3 C7 O1 -176.91(14) . . . . ? N1 C3 C7 O2 3.6(3) . . . . ? N2 C12 C16 O3 -177.03(13) . . . . ? N2 C12 C16 O4 4.9(3) . . . . ? C1 C2 C3 N1 -0.38(17) . . . . ? C1 C2 C3 C7 178.12(15) . . . . ? C2 C1 C4 N1 -0.49(16) . . . . ? C2 C1 C4 C6 179.40(15) . . . . ? C2 C3 C7 O1 4.8(2) . . . . ? C2 C3 C7 O2 -174.64(19) . . . . ? C3 N1 C4 C1 0.26(16) . . . . ? C3 N1 C4 C6 -179.64(14) . . . . ? C4 N1 C3 C2 0.08(16) . . . . ? C4 N1 C3 C7 -178.48(14) . . . . ? C4 C1 C2 C3 0.54(17) . . . . ? C5 N1 C3 C2 179.99(15) . . . . ? C5 N1 C3 C7 1.4(2) . . . . ? C5 N1 C4 C1 -179.66(15) . . . . ? C5 N1 C4 C6 0.4(2) . . . . ? C7 O1 C8 C9 -170.72(18) . . . . ? C8 O1 C7 O2 0.7(3) . . . . ? C8 O1 C7 C3 -178.76(14) . . . . ? C10 C11 C12 N2 -0.14(16) . . . . ? C10 C11 C12 C16 176.93(14) . . . . ? C11 C10 C13 N2 0.50(16) . . . . ? C11 C10 C13 C15 -177.78(16) . . . . ? C11 C12 C16 O3 6.4(2) . . . . ? C11 C12 C16 O4 -171.70(17) . . . . ? C12 N2 C13 C10 -0.59(16) . . . . ? C12 N2 C13 C15 177.83(14) . . . . ? C13 N2 C12 C11 0.46(16) . . . . ? C13 N2 C12 C16 -176.74(13) . . . . ? C13 C10 C11 C12 -0.21(16) . . . . ? C14 N2 C12 C11 -173.83(14) . . . . ? C14 N2 C12 C16 9.0(2) . . . . ? C14 N2 C13 C10 173.84(14) . . . . ? C14 N2 C13 C15 -7.7(2) . . . . ? C16 O3 C17 C18 178.55(15) . . . . ? C17 O3 C16 O4 2.3(2) . . . . ? C17 O3 C16 C12 -175.86(14) . . . . ?