#------------------------------------------------------------------------------ #$Date: 2019-12-21 03:46:13 +0200 (Sat, 21 Dec 2019) $ #$Revision: 245466 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125683.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_7125683 loop_ _publ_author_name 'Shoji, Taku' 'Sugiyama, Shuhei' 'Kobayashi, Yoshiaki' 'Yamazaki, Akari' 'Ariga, Yukino' 'Katoh, Ryuzi' 'Wakui, Hiroki' 'Yasunami, Masafumi' 'Ito, Shunji' _publ_section_title ; Direct synthesis of 2-arylazulenes by [8 + 2] cycloaddition of 2H-cyclohepta[b]furan-2-ones with silyl enol ethers ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC09376A _journal_year 2020 _chemical_formula_moiety 'C13 H9 N S' _chemical_formula_sum 'C13 H9 N S' _chemical_formula_weight 211.27 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2018-12-07 deposited with the CCDC. 2019-12-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 102.832(5) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 10.6375(5) _cell_length_b 16.3123(7) _cell_length_c 12.1927(6) _cell_measurement_reflns_used 13331 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.80 _cell_measurement_theta_min 2.10 _cell_volume 2062.86(17) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_molecular_graphics 'CrystalStructure 4.3.1 (Rigaku, 2018)' _computing_publication_material 'CrystalStructure 4.3.1 (Rigaku, 2018)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 7.111 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Rigaku Varimax with Saturn' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0982 _diffrn_reflns_av_unetI/netI 0.0676 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 34881 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.000 _diffrn_reflns_theta_min 2.120 _diffrn_source 'rotating anode X-ray generator' _exptl_absorpt_coefficient_mu 0.274 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_correction_T_min 0.748 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 880 _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.020 _refine_diff_density_max 0.383 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.071 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 271 _refine_ls_number_reflns 4970 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0855 _refine_ls_R_factor_gt 0.0550 _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^)+(0.0347P)^2^+1.6550P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1036 _refine_ls_wR_factor_ref 0.1155 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3610 _reflns_number_total 4970 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc09376a2.cif _cod_data_source_block shelxl_CCDC1 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7125683 _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 0.968 _shelx_estimated_absorpt_t_max 0.995 _shelx_res_file ; TITL xcalibur shelxl.res created by SHELXL-2018/3 at 18:26:49 on 04-Dec-2018 CELL 0.71073 10.63750 16.31230 12.19270 90.00000 102.83200 90.00000 ZERR 8 0.00050 0.00070 0.00060 0.00000 0.00500 0.00000 LATT 1 SYMM .50-X, .50+Y, .50-Z SFAC C H N S UNIT 104 72 8 8 SHEL 99999.000000 0.756947 L.S. 10 FMAP 2 PLAN 5 WPDB -2 HTAB BOND $H CONF LIST 4 TEMP -173.0 ACTA SIZE 0.120 0.120 0.020 WGHT 0.034700 1.655000 FVAR 0.47700 S1 4 0.499588 0.399679 0.700752 11.00000 0.02924 0.01879 = 0.02780 -0.00551 0.00223 0.00657 S2 4 0.537092 0.742203 0.528038 11.00000 0.01704 0.01854 = 0.01922 0.00045 0.00620 0.00182 N1 3 0.512452 0.502389 0.862168 11.00000 0.01985 0.02118 = 0.01948 -0.00088 0.00481 0.00045 N2 3 0.718637 0.759825 0.420535 11.00000 0.01780 0.01886 = 0.01591 0.00576 0.00353 0.00176 C1 1 0.391728 0.556349 0.682543 11.00000 0.01192 0.01680 = 0.01820 -0.00105 0.00551 -0.00267 C2 1 0.343802 0.552374 0.565194 11.00000 0.01516 0.01662 = 0.01809 -0.00334 0.00668 -0.00284 AFIX 43 H2 2 0.353918 0.507474 0.518284 11.00000 -1.20000 AFIX 0 C3 1 0.278783 0.625602 0.529195 11.00000 0.01268 0.01958 = 0.01845 -0.00249 0.00401 -0.00572 C4 1 0.217694 0.645231 0.418904 11.00000 0.01942 0.02164 = 0.01753 -0.00156 0.00502 -0.00902 AFIX 43 H4 2 0.217112 0.603347 0.364656 11.00000 -1.20000 AFIX 0 C5 1 0.157524 0.718242 0.378144 11.00000 0.02380 0.03059 = 0.01905 0.00722 -0.00027 -0.00692 AFIX 43 H5 2 0.122021 0.719641 0.299465 11.00000 -1.20000 AFIX 0 C6 1 0.142042 0.789347 0.436233 11.00000 0.01507 0.02450 = 0.03288 0.00840 0.00482 -0.00086 AFIX 43 H6 2 0.100508 0.833102 0.390826 11.00000 -1.20000 AFIX 0 C7 1 0.177983 0.806411 0.550724 11.00000 0.01844 0.01824 = 0.03140 0.00018 0.00886 0.00091 AFIX 43 H7 2 0.156603 0.859654 0.572388 11.00000 -1.20000 AFIX 0 C8 1 0.240620 0.756339 0.637239 11.00000 0.01729 0.01858 = 0.02378 -0.00208 0.01084 -0.00122 AFIX 43 H8 2 0.253372 0.779127 0.710588 11.00000 -1.20000 AFIX 0 C9 1 0.287502 0.677281 0.631726 11.00000 0.01123 0.01802 = 0.01874 -0.00114 0.00596 -0.00298 C10 1 0.356365 0.631719 0.722678 11.00000 0.01390 0.01851 = 0.01663 -0.00377 0.00547 -0.00163 AFIX 43 H10 2 0.375987 0.648920 0.799025 11.00000 -1.20000 AFIX 0 C11 1 0.465900 0.493595 0.753543 11.00000 0.01249 0.01588 = 0.02195 -0.00268 0.00701 -0.00233 C12 1 0.581048 0.371645 0.832332 11.00000 0.01911 0.01929 = 0.03405 0.00627 0.00594 0.00318 AFIX 43 H12 2 0.622743 0.320384 0.850877 11.00000 -1.20000 AFIX 0 C13 1 0.577666 0.432749 0.906125 11.00000 0.02034 0.02677 = 0.02252 0.00937 0.00461 -0.00033 AFIX 43 H13 2 0.617815 0.428012 0.983649 11.00000 -1.20000 AFIX 0 C14 1 0.768976 0.659291 0.575427 11.00000 0.01262 0.01375 = 0.01469 -0.00446 0.00061 -0.00306 C15 1 0.735495 0.619383 0.667421 11.00000 0.01498 0.01728 = 0.01347 -0.00299 0.00487 -0.00222 AFIX 43 H15 2 0.659366 0.628739 0.694147 11.00000 -1.20000 AFIX 0 C16 1 0.833008 0.563804 0.712654 11.00000 0.01532 0.01370 = 0.01357 -0.00388 0.00162 -0.00271 C17 1 0.835048 0.514872 0.806210 11.00000 0.02253 0.01503 = 0.01676 -0.00017 0.00640 -0.00147 AFIX 43 H17 2 0.763265 0.520595 0.840088 11.00000 -1.20000 AFIX 0 C18 1 0.927699 0.458878 0.856689 11.00000 0.02698 0.01783 = 0.01974 0.00352 0.00587 -0.00012 AFIX 43 H18 2 0.911976 0.432009 0.921463 11.00000 -1.20000 AFIX 0 C19 1 1.041685 0.436639 0.824726 11.00000 0.02153 0.01920 = 0.02650 0.00654 -0.00009 0.00319 AFIX 43 H19 2 1.092232 0.396358 0.870820 11.00000 -1.20000 AFIX 0 C20 1 1.091658 0.464655 0.735892 11.00000 0.01676 0.02187 = 0.03226 0.00300 0.00462 0.00193 AFIX 43 H20 2 1.170625 0.440071 0.729359 11.00000 -1.20000 AFIX 0 C21 1 1.043390 0.523318 0.655066 11.00000 0.01503 0.01809 = 0.02359 -0.00245 0.00716 -0.00421 AFIX 43 H21 2 1.093678 0.533368 0.601092 11.00000 -1.20000 AFIX 0 C22 1 0.931163 0.569274 0.642738 11.00000 0.01536 0.01307 = 0.01631 -0.00338 0.00307 -0.00441 C23 1 0.887934 0.629077 0.561089 11.00000 0.01347 0.01781 = 0.01637 0.00042 0.00422 -0.00295 AFIX 43 H23 2 0.931693 0.646426 0.505175 11.00000 -1.20000 AFIX 0 C24 1 0.689116 0.720264 0.506226 11.00000 0.01561 0.01351 = 0.01570 -0.00296 0.00383 -0.00105 C25 1 0.511643 0.806876 0.415973 11.00000 0.02162 0.01785 = 0.02090 0.00122 0.00029 0.00367 AFIX 43 H25 2 0.434740 0.837229 0.389144 11.00000 -1.20000 AFIX 0 C26 1 0.616333 0.808943 0.370546 11.00000 0.02538 0.02234 = 0.01947 0.00648 0.00428 0.00041 AFIX 43 H26 2 0.619401 0.842457 0.307472 11.00000 -1.20000 AFIX 0 HKLF 4 REM xcalibur REM wR2 = 0.1155, GooF = S = 1.035, Restrained GooF = 1.035 for all data REM R1 = 0.0550 for 3610 Fo > 4sig(Fo) and 0.0855 for all 4970 data REM 271 parameters refined using 0 restraints END WGHT 0.0347 1.6551 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.383, deepest hole -0.338, 1-sigma level 0.071 Q1 1 0.5011 0.5398 0.8979 11.00000 0.05 0.38 Q2 1 0.4584 0.4525 0.7240 11.00000 0.05 0.34 Q3 1 0.4985 0.7756 0.4651 11.00000 0.05 0.32 Q4 1 0.7295 0.6487 0.6174 11.00000 0.05 0.31 Q5 1 0.2758 0.6557 0.5759 11.00000 0.05 0.30 ; _shelx_res_checksum 71917 loop_ _space_group_symop_operation_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_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 S1 S 0.49959(6) 0.39968(4) 0.70075(6) 0.02592(17) Uani 1 1 d . . S2 S 0.53709(6) 0.74220(4) 0.52804(5) 0.01793(15) Uani 1 1 d . . N1 N 0.51245(19) 0.50239(12) 0.86217(17) 0.0201(4) Uani 1 1 d . . N2 N 0.71864(18) 0.75982(12) 0.42053(16) 0.0176(4) Uani 1 1 d . . C1 C 0.3917(2) 0.55635(14) 0.68254(19) 0.0153(5) Uani 1 1 d . . C2 C 0.3438(2) 0.55237(14) 0.56519(19) 0.0162(5) Uani 1 1 d . . H2 H 0.353918 0.507474 0.518284 0.019 Uiso 1 1 calc R U C3 C 0.2788(2) 0.62560(14) 0.52919(19) 0.0168(5) Uani 1 1 d . . C4 C 0.2177(2) 0.64523(15) 0.41890(19) 0.0194(5) Uani 1 1 d . . H4 H 0.217112 0.603347 0.364656 0.023 Uiso 1 1 calc R U C5 C 0.1575(2) 0.71824(16) 0.3781(2) 0.0253(6) Uani 1 1 d . . H5 H 0.122021 0.719641 0.299465 0.030 Uiso 1 1 calc R U C6 C 0.1420(2) 0.78935(16) 0.4362(2) 0.0242(6) Uani 1 1 d . . H6 H 0.100508 0.833102 0.390826 0.029 Uiso 1 1 calc R U C7 C 0.1780(2) 0.80641(15) 0.5507(2) 0.0222(5) Uani 1 1 d . . H7 H 0.156603 0.859654 0.572388 0.027 Uiso 1 1 calc R U C8 C 0.2406(2) 0.75634(14) 0.6372(2) 0.0189(5) Uani 1 1 d . . H8 H 0.253372 0.779127 0.710588 0.023 Uiso 1 1 calc R U C9 C 0.2875(2) 0.67728(14) 0.63173(19) 0.0156(5) Uani 1 1 d . . C10 C 0.3564(2) 0.63172(14) 0.72268(19) 0.0160(5) Uani 1 1 d . . H10 H 0.375987 0.648920 0.799025 0.019 Uiso 1 1 calc R U C11 C 0.4659(2) 0.49360(14) 0.7535(2) 0.0163(5) Uani 1 1 d . . C12 C 0.5810(2) 0.37164(15) 0.8323(2) 0.0241(6) Uani 1 1 d . . H12 H 0.622743 0.320384 0.850877 0.029 Uiso 1 1 calc R U C13 C 0.5777(2) 0.43275(15) 0.9061(2) 0.0232(6) Uani 1 1 d . . H13 H 0.617815 0.428012 0.983649 0.028 Uiso 1 1 calc R U C14 C 0.7690(2) 0.65929(13) 0.57543(18) 0.0141(5) Uani 1 1 d . . C15 C 0.7355(2) 0.61938(14) 0.66742(18) 0.0150(5) Uani 1 1 d . . H15 H 0.659366 0.628739 0.694147 0.018 Uiso 1 1 calc R U C16 C 0.8330(2) 0.56380(13) 0.71265(18) 0.0144(5) Uani 1 1 d . . C17 C 0.8350(2) 0.51487(14) 0.80621(19) 0.0178(5) Uani 1 1 d . . H17 H 0.763265 0.520595 0.840088 0.021 Uiso 1 1 calc R U C18 C 0.9277(2) 0.45888(15) 0.8567(2) 0.0214(5) Uani 1 1 d . . H18 H 0.911976 0.432009 0.921463 0.026 Uiso 1 1 calc R U C19 C 1.0417(2) 0.43664(15) 0.8247(2) 0.0233(6) Uani 1 1 d . . H19 H 1.092232 0.396358 0.870820 0.028 Uiso 1 1 calc R U C20 C 1.0917(2) 0.46466(15) 0.7359(2) 0.0238(6) Uani 1 1 d . . H20 H 1.170625 0.440071 0.729359 0.029 Uiso 1 1 calc R U C21 C 1.0434(2) 0.52332(14) 0.6551(2) 0.0185(5) Uani 1 1 d . . H21 H 1.093678 0.533368 0.601092 0.022 Uiso 1 1 calc R U C22 C 0.9312(2) 0.56927(13) 0.64274(19) 0.0150(5) Uani 1 1 d . . C23 C 0.8879(2) 0.62908(14) 0.56109(19) 0.0157(5) Uani 1 1 d . . H23 H 0.931693 0.646426 0.505175 0.019 Uiso 1 1 calc R U C24 C 0.6891(2) 0.72026(13) 0.50623(18) 0.0149(5) Uani 1 1 d . . C25 C 0.5116(2) 0.80688(14) 0.41597(19) 0.0208(5) Uani 1 1 d . . H25 H 0.434740 0.837229 0.389144 0.025 Uiso 1 1 calc R U C26 C 0.6163(2) 0.80894(15) 0.3705(2) 0.0225(5) Uani 1 1 d . . H26 H 0.619401 0.842457 0.307472 0.027 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 0.0292(4) 0.0188(3) 0.0278(4) -0.0055(3) 0.0022(3) 0.0066(3) S2 0.0170(3) 0.0185(3) 0.0192(3) 0.0004(2) 0.0062(2) 0.0018(2) N1 0.0199(11) 0.0212(11) 0.0195(11) -0.0009(8) 0.0048(9) 0.0004(8) N2 0.0178(10) 0.0189(10) 0.0159(10) 0.0058(8) 0.0035(8) 0.0018(8) C1 0.0119(11) 0.0168(12) 0.0182(12) -0.0010(9) 0.0055(9) -0.0027(9) C2 0.0152(11) 0.0166(11) 0.0181(12) -0.0033(9) 0.0067(10) -0.0028(9) C3 0.0127(11) 0.0196(12) 0.0184(12) -0.0025(10) 0.0040(10) -0.0057(9) C4 0.0194(12) 0.0216(13) 0.0175(12) -0.0016(10) 0.0050(10) -0.0090(10) C5 0.0238(13) 0.0306(15) 0.0190(13) 0.0072(11) -0.0003(11) -0.0069(11) C6 0.0151(12) 0.0245(13) 0.0329(15) 0.0084(12) 0.0048(11) -0.0009(10) C7 0.0184(12) 0.0182(12) 0.0314(14) 0.0002(11) 0.0089(11) 0.0009(10) C8 0.0173(12) 0.0186(12) 0.0238(13) -0.0021(10) 0.0108(10) -0.0012(10) C9 0.0112(11) 0.0180(12) 0.0187(12) -0.0011(9) 0.0060(9) -0.0030(9) C10 0.0139(11) 0.0185(12) 0.0166(12) -0.0038(10) 0.0055(10) -0.0016(9) C11 0.0125(11) 0.0159(12) 0.0219(13) -0.0027(10) 0.0070(10) -0.0023(9) C12 0.0191(13) 0.0193(13) 0.0341(15) 0.0063(11) 0.0059(11) 0.0032(10) C13 0.0203(13) 0.0268(14) 0.0225(13) 0.0094(11) 0.0046(11) -0.0003(10) C14 0.0126(11) 0.0138(11) 0.0147(11) -0.0045(9) 0.0006(9) -0.0031(9) C15 0.0150(11) 0.0173(12) 0.0135(11) -0.0030(9) 0.0049(9) -0.0022(9) C16 0.0153(11) 0.0137(11) 0.0136(11) -0.0039(9) 0.0016(9) -0.0027(9) C17 0.0225(13) 0.0150(11) 0.0168(12) -0.0002(9) 0.0064(10) -0.0015(10) C18 0.0270(14) 0.0178(12) 0.0197(13) 0.0035(10) 0.0059(11) -0.0001(10) C19 0.0215(13) 0.0192(12) 0.0265(14) 0.0065(11) -0.0001(11) 0.0032(10) C20 0.0168(12) 0.0219(13) 0.0323(15) 0.0030(11) 0.0046(11) 0.0019(10) C21 0.0150(12) 0.0181(12) 0.0236(13) -0.0024(10) 0.0072(10) -0.0042(9) C22 0.0154(11) 0.0131(11) 0.0163(11) -0.0034(9) 0.0031(9) -0.0044(9) C23 0.0135(11) 0.0178(12) 0.0164(11) 0.0004(9) 0.0042(9) -0.0029(9) C24 0.0156(11) 0.0135(11) 0.0157(11) -0.0030(9) 0.0038(9) -0.0010(9) C25 0.0216(13) 0.0178(12) 0.0209(13) 0.0012(10) 0.0003(10) 0.0037(10) C26 0.0254(14) 0.0223(13) 0.0195(13) 0.0065(10) 0.0043(11) 0.0004(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' 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 C12 S1 C11 89.51(12) C25 S2 C24 89.56(11) C11 N1 C13 110.3(2) C24 N2 C26 109.25(19) C10 C1 C2 109.2(2) C10 C1 C11 124.1(2) C2 C1 C11 126.7(2) C3 C2 C1 108.7(2) C3 C2 H2 125.6 C1 C2 H2 125.6 C4 C3 C2 126.1(2) C4 C3 C9 127.3(2) C2 C3 C9 106.5(2) C5 C4 C3 128.3(2) C5 C4 H4 115.8 C3 C4 H4 115.8 C6 C5 C4 129.1(2) C6 C5 H5 115.4 C4 C5 H5 115.4 C5 C6 C7 129.9(2) C5 C6 H6 115.0 C7 C6 H6 115.0 C8 C7 C6 128.7(2) C8 C7 H7 115.6 C6 C7 H7 115.6 C7 C8 C9 128.9(2) C7 C8 H8 115.5 C9 C8 H8 115.5 C8 C9 C10 125.8(2) C8 C9 C3 127.4(2) C10 C9 C3 106.7(2) C9 C10 C1 108.8(2) C9 C10 H10 125.6 C1 C10 H10 125.6 N1 C11 C1 123.8(2) N1 C11 S1 114.12(17) C1 C11 S1 122.11(17) C13 C12 S1 110.22(19) C13 C12 H12 124.9 S1 C12 H12 124.9 C12 C13 N1 115.9(2) C12 C13 H13 122.1 N1 C13 H13 122.1 C23 C14 C15 109.3(2) C23 C14 C24 126.6(2) C15 C14 C24 124.1(2) C16 C15 C14 108.5(2) C16 C15 H15 125.7 C14 C15 H15 125.7 C17 C16 C15 124.9(2) C17 C16 C22 128.3(2) C15 C16 C22 106.78(19) C18 C17 C16 128.6(2) C18 C17 H17 115.7 C16 C17 H17 115.7 C17 C18 C19 128.5(2) C17 C18 H18 115.8 C19 C18 H18 115.8 C20 C19 C18 129.6(2) C20 C19 H19 115.2 C18 C19 H19 115.2 C19 C20 C21 129.6(2) C19 C20 H20 115.2 C21 C20 H20 115.2 C20 C21 C22 128.5(2) C20 C21 H21 115.8 C22 C21 H21 115.8 C21 C22 C23 126.4(2) C21 C22 C16 126.9(2) C23 C22 C16 106.74(19) C22 C23 C14 108.6(2) C22 C23 H23 125.7 C14 C23 H23 125.7 N2 C24 C14 125.6(2) N2 C24 S2 114.42(17) C14 C24 S2 119.87(16) C26 C25 S2 110.29(18) C26 C25 H25 124.9 S2 C25 H25 124.9 C25 C26 N2 116.5(2) C25 C26 H26 121.8 N2 C26 H26 121.8 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C12 1.708(3) S1 C11 1.730(2) S2 C25 1.700(2) S2 C24 1.734(2) N1 C11 1.315(3) N1 C13 1.376(3) N2 C24 1.324(3) N2 C26 1.380(3) C1 C10 1.405(3) C1 C2 1.410(3) C1 C11 1.455(3) C2 C3 1.401(3) C2 H2 0.9500 C3 C4 1.395(3) C3 C9 1.494(3) C4 C5 1.391(3) C4 H4 0.9500 C5 C6 1.388(4) C5 H5 0.9500 C6 C7 1.391(3) C6 H6 0.9500 C7 C8 1.383(3) C7 H7 0.9500 C8 C9 1.390(3) C8 H8 0.9500 C9 C10 1.399(3) C10 H10 0.9500 C12 C13 1.349(4) C12 H12 0.9500 C13 H13 0.9500 C14 C23 1.405(3) C14 C15 1.409(3) C14 C24 1.451(3) C15 C16 1.396(3) C15 H15 0.9500 C16 C17 1.388(3) C16 C22 1.490(3) C17 C18 1.384(3) C17 H17 0.9500 C18 C19 1.401(3) C18 H18 0.9500 C19 C20 1.386(3) C19 H19 0.9500 C20 C21 1.388(3) C20 H20 0.9500 C21 C22 1.389(3) C21 H21 0.9500 C22 C23 1.397(3) C23 H23 0.9500 C25 C26 1.350(3) C25 H25 0.9500 C26 H26 0.9500 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 C10 C1 C2 C3 0.7(3) C11 C1 C2 C3 -179.5(2) C1 C2 C3 C4 -179.9(2) C1 C2 C3 C9 -0.2(2) C2 C3 C4 C5 -176.6(2) C9 C3 C4 C5 3.8(4) C3 C4 C5 C6 -0.6(4) C4 C5 C6 C7 -2.5(4) C5 C6 C7 C8 0.8(4) C6 C7 C8 C9 2.4(4) C7 C8 C9 C10 176.3(2) C7 C8 C9 C3 -1.5(4) C4 C3 C9 C8 -2.5(4) C2 C3 C9 C8 177.8(2) C4 C3 C9 C10 179.3(2) C2 C3 C9 C10 -0.4(2) C8 C9 C10 C1 -177.4(2) C3 C9 C10 C1 0.8(2) C2 C1 C10 C9 -1.0(3) C11 C1 C10 C9 179.2(2) C13 N1 C11 C1 179.8(2) C13 N1 C11 S1 0.2(2) C10 C1 C11 N1 -3.1(3) C2 C1 C11 N1 177.1(2) C10 C1 C11 S1 176.55(18) C2 C1 C11 S1 -3.2(3) C12 S1 C11 N1 -0.25(19) C12 S1 C11 C1 -179.93(19) C11 S1 C12 C13 0.25(19) S1 C12 C13 N1 -0.2(3) C11 N1 C13 C12 0.0(3) C23 C14 C15 C16 0.3(3) C24 C14 C15 C16 178.8(2) C14 C15 C16 C17 178.2(2) C14 C15 C16 C22 -0.9(2) C15 C16 C17 C18 -179.6(2) C22 C16 C17 C18 -0.6(4) C16 C17 C18 C19 -1.2(4) C17 C18 C19 C20 0.4(5) C18 C19 C20 C21 1.0(5) C19 C20 C21 C22 -0.1(5) C20 C21 C22 C23 178.5(2) C20 C21 C22 C16 -2.3(4) C17 C16 C22 C21 2.8(4) C15 C16 C22 C21 -178.1(2) C17 C16 C22 C23 -177.9(2) C15 C16 C22 C23 1.2(2) C21 C22 C23 C14 178.3(2) C16 C22 C23 C14 -1.0(2) C15 C14 C23 C22 0.5(3) C24 C14 C23 C22 -178.0(2) C26 N2 C24 C14 176.2(2) C26 N2 C24 S2 -0.2(2) C23 C14 C24 N2 -2.9(4) C15 C14 C24 N2 178.8(2) C23 C14 C24 S2 173.29(18) C15 C14 C24 S2 -5.0(3) C25 S2 C24 N2 0.52(19) C25 S2 C24 C14 -176.11(19) C24 S2 C25 C26 -0.64(19) S2 C25 C26 N2 0.7(3) C24 N2 C26 C25 -0.3(3)