# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Ying Cheng' _publ_contact_author_address ; Chemistry Department Beijing Normal University Xin Jie Kou Wai Da Jie 19, Beijing Beijing 100875 CHINA ; _publ_contact_author_email YCHENG2@BNU.EDU.CN _publ_section_title ; A N-heterocyclic carbene derived highly regioselective ambident C-C-S and C-C-N 1,3-dipolar system ; loop_ _publ_author_name 'Ying Cheng' 'Mei-Fang Liu' 'Bo Wang' # Attachment 'Revised-3c-Y. Cheng.cif' data_41216c _database_code_depnum_ccdc_archive 'CCDC 286158' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Dimethyl 1,3-dibenzyl-2'-phenylimino-2',3'- dihydrospiro(benzimidazoline-2,3'-thiophene)-4',5'-dicarboxylate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H29 N3 O4 S' _chemical_formula_weight 575.66 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.114(3) _cell_length_b 14.156(3) _cell_length_c 19.352(5) _cell_angle_alpha 80.220(4) _cell_angle_beta 85.469(4) _cell_angle_gamma 89.231(4) _cell_volume 2991.0(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1589 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 19.08 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.151 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16183 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.1032 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.00 _reflns_number_total 10405 _reflns_number_gt 5168 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0494P)^2^+0.1860P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0060(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 10405 _refine_ls_number_parameters 762 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1297 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1536 _refine_ls_wR_factor_gt 0.1239 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6316(2) 0.7362(2) 0.48166(16) 0.0447(7) Uani 1 1 d . . . C2 C 0.7830(3) 0.8245(2) 0.51605(16) 0.0447(7) Uani 1 1 d . . . C3 C 0.8843(3) 0.8784(2) 0.51835(19) 0.0602(9) Uani 1 1 d . . . H3 H 0.9225 0.9131 0.4776 0.072 Uiso 1 1 calc R . . C4 C 0.9270(3) 0.8792(2) 0.5831(2) 0.0685(10) Uani 1 1 d . . . H4 H 0.9947 0.9156 0.5863 0.082 Uiso 1 1 calc R . . C5 C 0.8718(3) 0.8273(2) 0.6428(2) 0.0665(10) Uani 1 1 d . . . H5 H 0.9025 0.8290 0.6859 0.080 Uiso 1 1 calc R . . C6 C 0.7702(3) 0.7718(2) 0.64033(18) 0.0582(9) Uani 1 1 d . . . H6 H 0.7331 0.7361 0.6810 0.070 Uiso 1 1 calc R . . C7 C 0.7267(3) 0.7714(2) 0.57653(17) 0.0459(8) Uani 1 1 d . . . C8 C 0.6769(3) 0.6426(2) 0.45630(16) 0.0490(8) Uani 1 1 d . . . C9 C 0.4752(3) 0.6939(2) 0.41378(16) 0.0478(8) Uani 1 1 d . . . C10 C 0.5114(2) 0.7572(2) 0.45045(16) 0.0465(8) Uani 1 1 d . . . C11 C 0.7753(3) 0.8245(2) 0.38854(17) 0.0568(9) Uani 1 1 d . . . H11A H 0.7227 0.7974 0.3593 0.068 Uiso 1 1 calc R . . H11B H 0.8491 0.7870 0.3903 0.068 Uiso 1 1 calc R . . C12 C 0.8057(3) 0.9259(2) 0.35437(16) 0.0504(8) Uani 1 1 d . . . C13 C 0.8944(3) 0.9407(3) 0.29942(18) 0.0657(10) Uani 1 1 d . . . H13 H 0.9364 0.8884 0.2863 0.079 Uiso 1 1 calc R . . C14 C 0.9217(3) 1.0320(3) 0.26348(19) 0.0759(11) Uani 1 1 d . . . H14 H 0.9800 1.0408 0.2257 0.091 Uiso 1 1 calc R . . C15 C 0.8625(3) 1.1085(3) 0.2840(2) 0.0711(11) Uani 1 1 d . . . H15 H 0.8803 1.1700 0.2599 0.085 Uiso 1 1 calc R . . C16 C 0.7777(3) 1.0962(3) 0.3392(2) 0.0675(10) Uani 1 1 d . . . H16 H 0.7388 1.1491 0.3533 0.081 Uiso 1 1 calc R . . C17 C 0.7492(3) 1.0047(2) 0.37449(18) 0.0600(9) Uani 1 1 d . . . H17 H 0.6910 0.9966 0.4123 0.072 Uiso 1 1 calc R . . C18 C 0.5740(3) 0.6390(2) 0.59900(17) 0.0593(9) Uani 1 1 d . . . H18A H 0.6357 0.5897 0.6010 0.071 Uiso 1 1 calc R . . H18B H 0.5081 0.6183 0.5750 0.071 Uiso 1 1 calc R . . C19 C 0.5283(3) 0.6479(2) 0.67241(17) 0.0551(8) Uani 1 1 d . . . C20 C 0.5405(3) 0.5726(3) 0.7259(2) 0.0793(11) Uani 1 1 d . . . H20 H 0.5790 0.5168 0.7166 0.095 Uiso 1 1 calc R . . C21 C 0.4963(4) 0.5788(4) 0.7934(2) 0.1008(14) Uani 1 1 d . . . H21 H 0.5031 0.5264 0.8291 0.121 Uiso 1 1 calc R . . C22 C 0.4426(4) 0.6611(4) 0.8088(2) 0.0981(14) Uani 1 1 d . . . H22 H 0.4153 0.6659 0.8548 0.118 Uiso 1 1 calc R . . C23 C 0.4299(3) 0.7357(3) 0.7557(2) 0.0820(11) Uani 1 1 d . . . H23 H 0.3930 0.7918 0.7654 0.098 Uiso 1 1 calc R . . C24 C 0.4707(3) 0.7295(3) 0.6880(2) 0.0681(10) Uani 1 1 d . . . H24 H 0.4594 0.7808 0.6521 0.082 Uiso 1 1 calc R . . C25 C 0.8287(3) 0.5260(2) 0.45077(17) 0.0587(9) Uani 1 1 d . . . C26 C 0.9455(3) 0.5285(3) 0.4208(2) 0.0851(12) Uani 1 1 d . . . H26 H 0.9884 0.5858 0.4120 0.102 Uiso 1 1 calc R . . C27 C 0.9983(4) 0.4464(4) 0.4040(3) 0.1050(15) Uani 1 1 d . . . H27 H 1.0758 0.4484 0.3818 0.126 Uiso 1 1 calc R . . C28 C 0.9370(5) 0.3618(4) 0.4198(2) 0.1079(16) Uani 1 1 d . . . H28 H 0.9741 0.3058 0.4100 0.129 Uiso 1 1 calc R . . C29 C 0.8214(5) 0.3586(3) 0.4500(2) 0.0956(14) Uani 1 1 d . . . H29 H 0.7796 0.3009 0.4600 0.115 Uiso 1 1 calc R . . C30 C 0.7674(3) 0.4409(2) 0.46548(19) 0.0739(11) Uani 1 1 d . . . H30 H 0.6888 0.4388 0.4861 0.089 Uiso 1 1 calc R . . C31 C 0.3609(3) 0.6916(3) 0.37860(18) 0.0571(9) Uani 1 1 d . . . C32 C 0.1753(3) 0.7686(3) 0.3586(2) 0.1038(15) Uani 1 1 d . . . H32A H 0.1863 0.7579 0.3109 0.156 Uiso 1 1 calc R . . H32B H 0.1394 0.8305 0.3597 0.156 Uiso 1 1 calc R . . H32C H 0.1234 0.7200 0.3857 0.156 Uiso 1 1 calc R . . C33 C 0.4438(3) 0.8452(2) 0.4651(2) 0.0546(9) Uani 1 1 d . . . C34 C 0.3913(4) 1.0022(3) 0.4155(2) 0.0953(13) Uani 1 1 d . . . H34A H 0.3063 0.9891 0.4190 0.143 Uiso 1 1 calc R . . H34B H 0.4116 1.0493 0.3744 0.143 Uiso 1 1 calc R . . H34C H 0.4117 1.0262 0.4566 0.143 Uiso 1 1 calc R . . C35 C 0.1614(3) 0.7068(2) 0.06688(16) 0.0515(8) Uani 1 1 d . . . C36 C 0.2302(3) 0.8181(2) -0.02853(18) 0.0524(8) Uani 1 1 d . . . C37 C 0.2530(3) 0.8679(2) -0.09537(19) 0.0643(9) Uani 1 1 d . . . H37 H 0.1980 0.8686 -0.1293 0.077 Uiso 1 1 calc R . . C38 C 0.3611(4) 0.9171(3) -0.1102(2) 0.0750(11) Uani 1 1 d . . . H38 H 0.3795 0.9516 -0.1551 0.090 Uiso 1 1 calc R . . C39 C 0.4412(3) 0.9159(3) -0.0604(2) 0.0782(11) Uani 1 1 d . . . H39 H 0.5126 0.9505 -0.0720 0.094 Uiso 1 1 calc R . . C40 C 0.4193(3) 0.8645(2) 0.0074(2) 0.0650(9) Uani 1 1 d . . . H40 H 0.4739 0.8642 0.0415 0.078 Uiso 1 1 calc R . . C41 C 0.3131(3) 0.8143(2) 0.02134(18) 0.0529(8) Uani 1 1 d . . . C42 C 0.1902(3) 0.6028(2) 0.05686(19) 0.0541(8) Uani 1 1 d . . . C43 C 0.0263(3) 0.6094(3) 0.15216(19) 0.0657(10) Uani 1 1 d . . . C44 C 0.0599(3) 0.6985(2) 0.12410(18) 0.0586(9) Uani 1 1 d . . . C45 C 0.0484(3) 0.7244(2) -0.04118(19) 0.0669(10) Uani 1 1 d . . . H45A H 0.0040 0.6720 -0.0118 0.080 Uiso 1 1 calc R . . H45B H 0.0970 0.6980 -0.0772 0.080 Uiso 1 1 calc R . . C46 C -0.0405(3) 0.7947(2) -0.07627(18) 0.0591(9) Uani 1 1 d . . . C47 C -0.1045(3) 0.7671(3) -0.1273(2) 0.0792(11) Uani 1 1 d . . . H47 H -0.0871 0.7091 -0.1424 0.095 Uiso 1 1 calc R . . C48 C -0.1952(4) 0.8254(4) -0.1566(2) 0.1024(15) Uani 1 1 d . . . H48 H -0.2387 0.8062 -0.1910 0.123 Uiso 1 1 calc R . . C49 C -0.2205(4) 0.9103(4) -0.1350(3) 0.1018(16) Uani 1 1 d . . . H49 H -0.2818 0.9489 -0.1545 0.122 Uiso 1 1 calc R . . C50 C -0.1571(4) 0.9395(3) -0.0853(3) 0.0946(14) Uani 1 1 d . . . H50 H -0.1742 0.9980 -0.0710 0.114 Uiso 1 1 calc R . . C51 C -0.0670(3) 0.8814(3) -0.0561(2) 0.0747(11) Uani 1 1 d . . . H51 H -0.0234 0.9015 -0.0221 0.090 Uiso 1 1 calc R . . C52 C 0.3419(3) 0.7026(2) 0.13345(19) 0.0676(10) Uani 1 1 d . . . H52A H 0.3990 0.6662 0.1079 0.081 Uiso 1 1 calc R . . H52B H 0.2926 0.6571 0.1666 0.081 Uiso 1 1 calc R . . C53 C 0.4108(3) 0.7625(3) 0.17376(18) 0.0618(9) Uani 1 1 d . . . C54 C 0.3636(3) 0.8446(3) 0.19436(19) 0.0724(10) Uani 1 1 d . . . H54 H 0.2872 0.8654 0.1821 0.087 Uiso 1 1 calc R . . C55 C 0.4285(4) 0.8961(3) 0.2329(2) 0.0793(11) Uani 1 1 d . . . H55 H 0.3961 0.9520 0.2460 0.095 Uiso 1 1 calc R . . C56 C 0.5409(4) 0.8655(3) 0.25220(19) 0.0769(11) Uani 1 1 d . . . H56 H 0.5849 0.9004 0.2781 0.092 Uiso 1 1 calc R . . C57 C 0.5867(3) 0.7835(3) 0.2328(2) 0.0780(11) Uani 1 1 d . . . H57 H 0.6622 0.7618 0.2461 0.094 Uiso 1 1 calc R . . C58 C 0.5228(3) 0.7327(3) 0.19410(18) 0.0685(10) Uani 1 1 d . . . H58 H 0.5556 0.6768 0.1813 0.082 Uiso 1 1 calc R . . C59 C 0.2889(3) 0.4907(2) -0.00182(18) 0.0594(9) Uani 1 1 d . . . C60 C 0.3649(6) 0.4332(3) 0.0366(3) 0.156(3) Uani 1 1 d . . . H60 H 0.4031 0.4561 0.0715 0.188 Uiso 1 1 calc R . . C61 C 0.3873(5) 0.3411(4) 0.0253(3) 0.148(3) Uani 1 1 d . . . H61 H 0.4409 0.3030 0.0524 0.178 Uiso 1 1 calc R . . C62 C 0.3349(4) 0.3066(3) -0.0224(2) 0.0813(12) Uani 1 1 d . . . H62 H 0.3502 0.2442 -0.0297 0.098 Uiso 1 1 calc R . . C63 C 0.2588(4) 0.3620(3) -0.0607(3) 0.1015(15) Uani 1 1 d . . . H63 H 0.2194 0.3375 -0.0944 0.122 Uiso 1 1 calc R . . C64 C 0.2372(3) 0.4551(3) -0.0513(2) 0.0874(13) Uani 1 1 d . . . H64 H 0.1860 0.4934 -0.0799 0.105 Uiso 1 1 calc R . . C65 C -0.0741(4) 0.5873(3) 0.2081(2) 0.0779(11) Uani 1 1 d . . . C66 C -0.2081(4) 0.4682(4) 0.2657(2) 0.1288(19) Uani 1 1 d . . . H66A H -0.1918 0.4796 0.3116 0.193 Uiso 1 1 calc R . . H66B H -0.2241 0.4012 0.2678 0.193 Uiso 1 1 calc R . . H66C H -0.2771 0.5050 0.2503 0.193 Uiso 1 1 calc R . . C67 C 0.0053(3) 0.7874(3) 0.1438(2) 0.0666(10) Uani 1 1 d . . . C68 C -0.1557(3) 0.8966(3) 0.1220(2) 0.0883(12) Uani 1 1 d . . . H68A H -0.1899 0.8912 0.1697 0.132 Uiso 1 1 calc R . . H68B H -0.2186 0.9092 0.0905 0.132 Uiso 1 1 calc R . . H68C H -0.0984 0.9482 0.1123 0.132 Uiso 1 1 calc R . . N1 N 0.6242(2) 0.72783(16) 0.55805(13) 0.0483(6) Uani 1 1 d . . . N2 N 0.7170(2) 0.81525(17) 0.45915(13) 0.0482(6) Uani 1 1 d . . . N3 N 0.7801(2) 0.61150(18) 0.47024(14) 0.0595(7) Uani 1 1 d . . . N4 N 0.1280(2) 0.76542(17) 0.00147(14) 0.0541(7) Uani 1 1 d . . . N5 N 0.2644(2) 0.75735(18) 0.08382(14) 0.0545(7) Uani 1 1 d . . . N6 N 0.2654(3) 0.58669(18) 0.00865(16) 0.0627(8) Uani 1 1 d . . . O1 O 0.3374(2) 0.62979(19) 0.34800(15) 0.0871(8) Uani 1 1 d . . . O2 O 0.29070(19) 0.76501(17) 0.38818(12) 0.0709(7) Uani 1 1 d . . . O3 O 0.3877(2) 0.84994(18) 0.51865(15) 0.0860(8) Uani 1 1 d . . . O4 O 0.45797(19) 0.91495(15) 0.41002(12) 0.0649(6) Uani 1 1 d . . . O5 O -0.1220(3) 0.6449(2) 0.23876(17) 0.1113(11) Uani 1 1 d . . . O6 O -0.1036(2) 0.4965(2) 0.21644(14) 0.0942(9) Uani 1 1 d . . . O7 O 0.0498(2) 0.8358(2) 0.17906(17) 0.1074(10) Uani 1 1 d . . . O8 O -0.0954(2) 0.80778(16) 0.11247(13) 0.0723(7) Uani 1 1 d . . . S1 S 0.57149(7) 0.59554(6) 0.40733(5) 0.0587(3) Uani 1 1 d . . . S2 S 0.10439(9) 0.51701(6) 0.11762(6) 0.0767(3) Uani 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 C1 0.0485(18) 0.0338(17) 0.054(2) -0.0123(14) -0.0080(15) -0.0005(14) C2 0.0485(18) 0.0401(18) 0.049(2) -0.0141(15) -0.0099(16) 0.0041(15) C3 0.059(2) 0.050(2) 0.071(3) -0.0039(17) -0.0136(18) 0.0013(17) C4 0.066(2) 0.062(2) 0.080(3) -0.011(2) -0.025(2) -0.0075(19) C5 0.075(2) 0.062(2) 0.069(3) -0.019(2) -0.028(2) -0.001(2) C6 0.066(2) 0.055(2) 0.056(2) -0.0119(16) -0.0113(17) -0.0040(17) C7 0.0484(18) 0.0404(18) 0.052(2) -0.0124(15) -0.0103(16) 0.0003(14) C8 0.0553(19) 0.0393(18) 0.053(2) -0.0096(14) -0.0062(16) -0.0020(15) C9 0.0525(18) 0.0392(18) 0.052(2) -0.0065(15) -0.0053(15) -0.0021(15) C10 0.0490(18) 0.0375(18) 0.052(2) -0.0046(15) -0.0042(15) 0.0005(14) C11 0.064(2) 0.050(2) 0.057(2) -0.0109(16) -0.0077(17) -0.0026(16) C12 0.0506(18) 0.053(2) 0.048(2) -0.0077(16) -0.0076(16) -0.0035(16) C13 0.064(2) 0.072(3) 0.059(2) -0.0096(19) 0.0030(19) -0.0004(19) C14 0.072(3) 0.095(3) 0.056(2) -0.003(2) 0.0045(19) -0.018(2) C15 0.077(3) 0.067(3) 0.065(3) 0.007(2) -0.017(2) -0.011(2) C16 0.065(2) 0.058(2) 0.075(3) 0.0038(19) -0.007(2) 0.0000(18) C17 0.056(2) 0.057(2) 0.064(2) -0.0037(18) 0.0013(17) 0.0021(17) C18 0.074(2) 0.042(2) 0.062(2) -0.0082(16) -0.0043(18) -0.0102(16) C19 0.060(2) 0.054(2) 0.050(2) -0.0042(17) -0.0062(16) -0.0066(17) C20 0.104(3) 0.070(3) 0.063(3) -0.005(2) -0.016(2) 0.005(2) C21 0.141(4) 0.097(4) 0.058(3) 0.007(2) -0.018(3) 0.010(3) C22 0.121(4) 0.113(4) 0.059(3) -0.014(3) -0.004(2) 0.005(3) C23 0.093(3) 0.086(3) 0.068(3) -0.023(2) 0.001(2) 0.013(2) C24 0.075(2) 0.064(2) 0.063(3) -0.0085(19) -0.002(2) 0.0081(19) C25 0.063(2) 0.057(2) 0.058(2) -0.0134(17) -0.0132(18) 0.0200(19) C26 0.066(3) 0.079(3) 0.114(4) -0.024(2) -0.011(2) 0.018(2) C27 0.081(3) 0.113(4) 0.122(4) -0.027(3) -0.004(3) 0.042(3) C28 0.146(5) 0.080(4) 0.095(4) -0.015(3) 0.001(3) 0.058(3) C29 0.139(4) 0.048(3) 0.092(3) -0.001(2) 0.012(3) 0.021(3) C30 0.091(3) 0.046(2) 0.079(3) -0.0004(19) 0.009(2) 0.014(2) C31 0.062(2) 0.049(2) 0.059(2) -0.0018(18) -0.0091(18) -0.0094(18) C32 0.057(2) 0.109(4) 0.145(4) -0.006(3) -0.040(3) 0.003(2) C33 0.054(2) 0.047(2) 0.067(3) -0.0185(19) -0.0131(19) 0.0035(16) C34 0.114(3) 0.053(2) 0.122(4) -0.019(2) -0.029(3) 0.035(2) C35 0.0558(19) 0.0441(19) 0.056(2) -0.0105(15) -0.0103(17) 0.0057(15) C36 0.059(2) 0.0414(19) 0.059(2) -0.0164(17) -0.0063(18) 0.0061(16) C37 0.070(2) 0.057(2) 0.066(3) -0.0107(19) -0.0085(19) 0.0091(19) C38 0.083(3) 0.061(2) 0.078(3) -0.011(2) 0.013(2) 0.004(2) C39 0.066(2) 0.060(3) 0.106(3) -0.015(2) 0.011(2) -0.0021(19) C40 0.061(2) 0.052(2) 0.085(3) -0.021(2) -0.0048(19) 0.0014(18) C41 0.056(2) 0.0397(19) 0.066(2) -0.0164(16) -0.0064(18) 0.0052(16) C42 0.058(2) 0.043(2) 0.062(2) -0.0080(16) -0.0132(18) 0.0069(16) C43 0.065(2) 0.060(2) 0.070(3) -0.0062(19) -0.0056(19) 0.0043(18) C44 0.062(2) 0.054(2) 0.061(2) -0.0133(17) -0.0096(18) 0.0045(17) C45 0.075(2) 0.051(2) 0.078(3) -0.0132(18) -0.024(2) 0.0027(18) C46 0.054(2) 0.058(2) 0.061(2) 0.0014(18) -0.0063(18) -0.0086(18) C47 0.078(3) 0.081(3) 0.077(3) -0.002(2) -0.017(2) -0.008(2) C48 0.087(3) 0.126(4) 0.089(3) 0.012(3) -0.033(3) -0.010(3) C49 0.079(3) 0.113(4) 0.101(4) 0.019(3) -0.012(3) 0.011(3) C50 0.088(3) 0.092(3) 0.095(3) 0.003(3) 0.001(3) 0.027(3) C51 0.076(2) 0.068(3) 0.079(3) -0.004(2) -0.012(2) 0.018(2) C52 0.074(2) 0.055(2) 0.078(3) -0.0123(18) -0.026(2) 0.0072(18) C53 0.064(2) 0.062(2) 0.058(2) -0.0066(18) -0.0079(18) 0.0021(19) C54 0.072(2) 0.071(3) 0.077(3) -0.015(2) -0.022(2) 0.003(2) C55 0.092(3) 0.075(3) 0.075(3) -0.018(2) -0.020(2) -0.003(2) C56 0.084(3) 0.087(3) 0.059(3) -0.004(2) -0.016(2) -0.017(2) C57 0.071(2) 0.095(3) 0.068(3) -0.008(2) -0.020(2) -0.002(2) C58 0.069(2) 0.074(3) 0.063(2) -0.0095(19) -0.013(2) 0.002(2) C59 0.067(2) 0.048(2) 0.065(2) -0.0152(17) -0.0094(19) 0.0049(17) C60 0.243(6) 0.093(4) 0.172(5) -0.079(3) -0.145(5) 0.088(4) C61 0.215(6) 0.094(4) 0.165(5) -0.068(4) -0.120(5) 0.090(4) C62 0.082(3) 0.052(2) 0.114(4) -0.029(2) -0.007(2) 0.011(2) C63 0.090(3) 0.074(3) 0.160(5) -0.060(3) -0.048(3) 0.016(2) C64 0.085(3) 0.063(3) 0.126(4) -0.035(2) -0.048(3) 0.016(2) C65 0.078(3) 0.078(3) 0.072(3) 0.005(2) -0.003(2) 0.002(2) C66 0.116(4) 0.168(5) 0.092(4) 0.004(3) 0.013(3) -0.065(4) C67 0.062(2) 0.063(3) 0.079(3) -0.024(2) -0.002(2) 0.003(2) C68 0.086(3) 0.068(3) 0.116(3) -0.035(2) -0.002(2) 0.021(2) N1 0.0548(15) 0.0410(15) 0.0491(17) -0.0061(12) -0.0064(12) -0.0041(12) N2 0.0519(15) 0.0439(15) 0.0491(17) -0.0079(12) -0.0055(13) -0.0044(12) N3 0.0610(17) 0.0488(17) 0.071(2) -0.0127(14) -0.0125(14) 0.0101(14) N4 0.0571(16) 0.0448(16) 0.0621(18) -0.0100(13) -0.0140(14) 0.0004(13) N5 0.0574(16) 0.0461(16) 0.0622(19) -0.0124(14) -0.0122(14) 0.0037(13) N6 0.0750(19) 0.0463(18) 0.069(2) -0.0127(14) -0.0110(16) 0.0072(15) O1 0.0877(18) 0.0747(19) 0.113(2) -0.0422(16) -0.0325(16) -0.0093(15) O2 0.0554(14) 0.0672(16) 0.0930(19) -0.0141(13) -0.0216(13) 0.0022(12) O3 0.101(2) 0.086(2) 0.0701(19) -0.0200(15) 0.0081(16) 0.0292(15) O4 0.0762(15) 0.0399(13) 0.0773(17) -0.0068(12) -0.0062(12) 0.0102(11) O5 0.113(2) 0.103(3) 0.105(3) 0.0000(19) 0.0331(19) 0.0180(19) O6 0.101(2) 0.100(2) 0.078(2) -0.0050(16) 0.0004(15) -0.0351(18) O7 0.0783(18) 0.127(3) 0.143(3) -0.094(2) -0.0185(18) 0.0115(17) O8 0.0751(16) 0.0551(15) 0.0910(19) -0.0234(13) -0.0117(14) 0.0110(13) S1 0.0668(5) 0.0427(5) 0.0710(6) -0.0182(4) -0.0149(4) 0.0009(4) S2 0.0812(6) 0.0474(6) 0.0974(8) -0.0033(5) -0.0017(5) 0.0017(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 N1 1.459(4) . ? C1 N2 1.464(3) . ? C1 C10 1.515(4) . ? C1 C8 1.553(4) . ? C2 C3 1.376(4) . ? C2 C7 1.387(4) . ? C2 N2 1.395(4) . ? C3 C4 1.377(4) . ? C3 H3 0.9300 . ? C4 C5 1.365(5) . ? C4 H4 0.9300 . ? C5 C6 1.392(4) . ? C5 H5 0.9300 . ? C6 C7 1.362(4) . ? C6 H6 0.9300 . ? C7 N1 1.402(3) . ? C8 N3 1.256(3) . ? C8 S1 1.767(3) . ? C9 C10 1.319(4) . ? C9 C31 1.491(4) . ? C9 S1 1.760(3) . ? C10 C33 1.503(4) . ? C11 N2 1.451(4) . ? C11 C12 1.505(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C17 1.372(4) . ? C12 C13 1.382(4) . ? C13 C14 1.385(5) . ? C13 H13 0.9300 . ? C14 C15 1.361(5) . ? C14 H14 0.9300 . ? C15 C16 1.357(5) . ? C15 H15 0.9300 . ? C16 C17 1.387(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 N1 1.460(4) . ? C18 C19 1.496(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.368(4) . ? C19 C24 1.380(4) . ? C20 C21 1.376(5) . ? C20 H20 0.9300 . ? C21 C22 1.369(6) . ? C21 H21 0.9300 . ? C22 C23 1.357(5) . ? C22 H22 0.9300 . ? C23 C24 1.369(5) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C30 1.369(5) . ? C25 C26 1.377(5) . ? C25 N3 1.416(4) . ? C26 C27 1.372(5) . ? C26 H26 0.9300 . ? C27 C28 1.362(6) . ? C27 H27 0.9300 . ? C28 C29 1.367(6) . ? C28 H28 0.9300 . ? C29 C30 1.369(5) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 O1 1.179(4) . ? C31 O2 1.320(4) . ? C32 O2 1.442(4) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 O3 1.178(4) . ? C33 O4 1.325(4) . ? C34 O4 1.447(4) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 N5 1.447(4) . ? C35 N4 1.462(4) . ? C35 C44 1.508(4) . ? C35 C42 1.543(4) . ? C36 C37 1.370(4) . ? C36 C41 1.380(4) . ? C36 N4 1.399(4) . ? C37 C38 1.382(5) . ? C37 H37 0.9300 . ? C38 C39 1.360(5) . ? C38 H38 0.9300 . ? C39 C40 1.394(5) . ? C39 H39 0.9300 . ? C40 C41 1.370(4) . ? C40 H40 0.9300 . ? C41 N5 1.408(4) . ? C42 N6 1.251(4) . ? C42 S2 1.771(3) . ? C43 C44 1.331(4) . ? C43 C65 1.490(5) . ? C43 S2 1.757(4) . ? C44 C67 1.483(5) . ? C45 N4 1.446(4) . ? C45 C46 1.508(4) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 C51 1.372(5) . ? C46 C47 1.373(5) . ? C47 C48 1.388(5) . ? C47 H47 0.9300 . ? C48 C49 1.357(6) . ? C48 H48 0.9300 . ? C49 C50 1.358(6) . ? C49 H49 0.9300 . ? C50 C51 1.381(5) . ? C50 H50 0.9300 . ? C51 H51 0.9300 . ? C52 N5 1.458(4) . ? C52 C53 1.500(5) . ? C52 H52A 0.9700 . ? C52 H52B 0.9700 . ? C53 C54 1.375(5) . ? C53 C58 1.375(4) . ? C54 C55 1.376(5) . ? C54 H54 0.9300 . ? C55 C56 1.376(5) . ? C55 H55 0.9300 . ? C56 C57 1.360(5) . ? C56 H56 0.9300 . ? C57 C58 1.365(5) . ? C57 H57 0.9300 . ? C58 H58 0.9300 . ? C59 C64 1.325(5) . ? C59 C60 1.344(5) . ? C59 N6 1.426(4) . ? C60 C61 1.374(6) . ? C60 H60 0.9300 . ? C61 C62 1.295(5) . ? C61 H61 0.9300 . ? C62 C63 1.328(5) . ? C62 H62 0.9300 . ? C63 C64 1.376(5) . ? C63 H63 0.9300 . ? C64 H64 0.9300 . ? C65 O5 1.184(5) . ? C65 O6 1.312(5) . ? C66 O6 1.458(4) . ? C66 H66A 0.9600 . ? C66 H66B 0.9600 . ? C66 H66C 0.9600 . ? C67 O7 1.184(4) . ? C67 O8 1.320(4) . ? C68 O8 1.449(4) . ? C68 H68A 0.9600 . ? C68 H68B 0.9600 . ? C68 H68C 0.9600 . ? 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 N1 C1 N2 102.3(2) . . ? N1 C1 C10 113.5(2) . . ? N2 C1 C10 111.9(2) . . ? N1 C1 C8 112.6(2) . . ? N2 C1 C8 112.0(2) . . ? C10 C1 C8 104.9(2) . . ? C3 C2 C7 121.4(3) . . ? C3 C2 N2 129.8(3) . . ? C7 C2 N2 108.8(3) . . ? C2 C3 C4 117.6(3) . . ? C2 C3 H3 121.2 . . ? C4 C3 H3 121.2 . . ? C5 C4 C3 121.2(3) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 121.1(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C7 C6 C5 118.1(3) . . ? C7 C6 H6 121.0 . . ? C5 C6 H6 121.0 . . ? C6 C7 C2 120.6(3) . . ? C6 C7 N1 131.1(3) . . ? C2 C7 N1 108.3(3) . . ? N3 C8 C1 119.0(3) . . ? N3 C8 S1 128.5(3) . . ? C1 C8 S1 112.5(2) . . ? C10 C9 C31 129.1(3) . . ? C10 C9 S1 116.4(2) . . ? C31 C9 S1 114.5(2) . . ? C9 C10 C33 126.3(3) . . ? C9 C10 C1 115.6(3) . . ? C33 C10 C1 118.0(3) . . ? N2 C11 C12 114.5(3) . . ? N2 C11 H11A 108.6 . . ? C12 C11 H11A 108.6 . . ? N2 C11 H11B 108.6 . . ? C12 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C17 C12 C13 118.0(3) . . ? C17 C12 C11 123.4(3) . . ? C13 C12 C11 118.6(3) . . ? C12 C13 C14 121.2(3) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C15 C14 C13 119.3(4) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C16 C15 C14 120.7(3) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 119.9(4) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C12 C17 C16 120.8(3) . . ? C12 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? N1 C18 C19 113.7(3) . . ? N1 C18 H18A 108.8 . . ? C19 C18 H18A 108.8 . . ? N1 C18 H18B 108.8 . . ? C19 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C20 C19 C24 118.3(4) . . ? C20 C19 C18 119.7(3) . . ? C24 C19 C18 121.9(3) . . ? C19 C20 C21 120.4(4) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C22 C21 C20 120.9(4) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C23 C22 C21 118.7(4) . . ? C23 C22 H22 120.6 . . ? C21 C22 H22 120.6 . . ? C22 C23 C24 121.0(4) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C23 C24 C19 120.7(3) . . ? C23 C24 H24 119.7 . . ? C19 C24 H24 119.7 . . ? C30 C25 C26 119.7(3) . . ? C30 C25 N3 122.3(3) . . ? C26 C25 N3 117.8(3) . . ? C27 C26 C25 119.9(4) . . ? C27 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? C28 C27 C26 119.9(4) . . ? C28 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? C27 C28 C29 120.5(4) . . ? C27 C28 H28 119.8 . . ? C29 C28 H28 119.8 . . ? C28 C29 C30 119.8(4) . . ? C28 C29 H29 120.1 . . ? C30 C29 H29 120.1 . . ? C25 C30 C29 120.2(4) . . ? C25 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? O1 C31 O2 125.7(3) . . ? O1 C31 C9 122.9(3) . . ? O2 C31 C9 111.3(3) . . ? O2 C32 H32A 109.5 . . ? O2 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? O2 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O3 C33 O4 126.0(3) . . ? O3 C33 C10 123.7(3) . . ? O4 C33 C10 110.3(3) . . ? O4 C34 H34A 109.5 . . ? O4 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O4 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N5 C35 N4 102.8(2) . . ? N5 C35 C44 112.3(3) . . ? N4 C35 C44 112.1(2) . . ? N5 C35 C42 113.3(2) . . ? N4 C35 C42 111.4(3) . . ? C44 C35 C42 105.2(3) . . ? C37 C36 C41 121.7(3) . . ? C37 C36 N4 129.4(3) . . ? C41 C36 N4 108.9(3) . . ? C36 C37 C38 117.2(3) . . ? C36 C37 H37 121.4 . . ? C38 C37 H37 121.4 . . ? C39 C38 C37 121.2(4) . . ? C39 C38 H38 119.4 . . ? C37 C38 H38 119.4 . . ? C38 C39 C40 122.0(4) . . ? C38 C39 H39 119.0 . . ? C40 C39 H39 119.0 . . ? C41 C40 C39 116.5(3) . . ? C41 C40 H40 121.7 . . ? C39 C40 H40 121.7 . . ? C40 C41 C36 121.4(3) . . ? C40 C41 N5 130.3(3) . . ? C36 C41 N5 108.2(3) . . ? N6 C42 C35 120.2(3) . . ? N6 C42 S2 127.0(3) . . ? C35 C42 S2 112.8(3) . . ? C44 C43 C65 123.0(4) . . ? C44 C43 S2 116.2(3) . . ? C65 C43 S2 120.8(3) . . ? C43 C44 C67 125.7(3) . . ? C43 C44 C35 115.4(3) . . ? C67 C44 C35 118.9(3) . . ? N4 C45 C46 114.2(3) . . ? N4 C45 H45A 108.7 . . ? C46 C45 H45A 108.7 . . ? N4 C45 H45B 108.7 . . ? C46 C45 H45B 108.7 . . ? H45A C45 H45B 107.6 . . ? C51 C46 C47 118.4(3) . . ? C51 C46 C45 123.3(3) . . ? C47 C46 C45 118.1(3) . . ? C46 C47 C48 120.3(4) . . ? C46 C47 H47 119.8 . . ? C48 C47 H47 119.8 . . ? C49 C48 C47 120.0(5) . . ? C49 C48 H48 120.0 . . ? C47 C48 H48 120.0 . . ? C48 C49 C50 120.6(4) . . ? C48 C49 H49 119.7 . . ? C50 C49 H49 119.7 . . ? C49 C50 C51 119.4(5) . . ? C49 C50 H50 120.3 . . ? C51 C50 H50 120.3 . . ? C46 C51 C50 121.2(4) . . ? C46 C51 H51 119.4 . . ? C50 C51 H51 119.4 . . ? N5 C52 C53 114.3(3) . . ? N5 C52 H52A 108.7 . . ? C53 C52 H52A 108.7 . . ? N5 C52 H52B 108.7 . . ? C53 C52 H52B 108.7 . . ? H52A C52 H52B 107.6 . . ? C54 C53 C58 118.2(4) . . ? C54 C53 C52 122.4(3) . . ? C58 C53 C52 119.4(3) . . ? C53 C54 C55 120.6(3) . . ? C53 C54 H54 119.7 . . ? C55 C54 H54 119.7 . . ? C56 C55 C54 120.4(4) . . ? C56 C55 H55 119.8 . . ? C54 C55 H55 119.8 . . ? C57 C56 C55 119.1(4) . . ? C57 C56 H56 120.5 . . ? C55 C56 H56 120.5 . . ? C56 C57 C58 120.6(4) . . ? C56 C57 H57 119.7 . . ? C58 C57 H57 119.7 . . ? C57 C58 C53 121.2(4) . . ? C57 C58 H58 119.4 . . ? C53 C58 H58 119.4 . . ? C64 C59 C60 117.2(4) . . ? C64 C59 N6 120.7(3) . . ? C60 C59 N6 122.0(4) . . ? C59 C60 C61 121.2(4) . . ? C59 C60 H60 119.4 . . ? C61 C60 H60 119.4 . . ? C62 C61 C60 121.0(4) . . ? C62 C61 H61 119.5 . . ? C60 C61 H61 119.5 . . ? C61 C62 C63 118.8(4) . . ? C61 C62 H62 120.6 . . ? C63 C62 H62 120.6 . . ? C62 C63 C64 121.1(4) . . ? C62 C63 H63 119.4 . . ? C64 C63 H63 119.4 . . ? C59 C64 C63 120.6(4) . . ? C59 C64 H64 119.7 . . ? C63 C64 H64 119.7 . . ? O5 C65 O6 125.5(4) . . ? O5 C65 C43 124.2(4) . . ? O6 C65 C43 110.2(4) . . ? O6 C66 H66A 109.5 . . ? O6 C66 H66B 109.5 . . ? H66A C66 H66B 109.5 . . ? O6 C66 H66C 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? O7 C67 O8 125.1(3) . . ? O7 C67 C44 124.6(3) . . ? O8 C67 C44 110.2(3) . . ? O8 C68 H68A 109.5 . . ? O8 C68 H68B 109.5 . . ? H68A C68 H68B 109.5 . . ? O8 C68 H68C 109.5 . . ? H68A C68 H68C 109.5 . . ? H68B C68 H68C 109.5 . . ? C7 N1 C1 108.2(2) . . ? C7 N1 C18 122.2(2) . . ? C1 N1 C18 117.0(2) . . ? C2 N2 C11 120.9(2) . . ? C2 N2 C1 108.1(2) . . ? C11 N2 C1 117.3(2) . . ? C8 N3 C25 123.4(3) . . ? C36 N4 C45 121.5(3) . . ? C36 N4 C35 107.1(2) . . ? C45 N4 C35 118.4(2) . . ? C41 N5 C35 107.7(2) . . ? C41 N5 C52 121.3(3) . . ? C35 N5 C52 116.0(2) . . ? C42 N6 C59 120.0(3) . . ? C31 O2 C32 116.4(3) . . ? C33 O4 C34 116.0(3) . . ? C65 O6 C66 115.1(4) . . ? C67 O8 C68 117.2(3) . . ? C9 S1 C8 90.50(15) . . ? C43 S2 C42 90.27(17) . . ? 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 C7 C2 C3 C4 -1.1(4) . . . . ? N2 C2 C3 C4 175.9(3) . . . . ? C2 C3 C4 C5 0.8(5) . . . . ? C3 C4 C5 C6 0.0(5) . . . . ? C4 C5 C6 C7 -0.6(5) . . . . ? C5 C6 C7 C2 0.3(4) . . . . ? C5 C6 C7 N1 -176.0(3) . . . . ? C3 C2 C7 C6 0.5(4) . . . . ? N2 C2 C7 C6 -177.0(3) . . . . ? C3 C2 C7 N1 177.6(3) . . . . ? N2 C2 C7 N1 0.0(3) . . . . ? N1 C1 C8 N3 -61.2(3) . . . . ? N2 C1 C8 N3 53.4(4) . . . . ? C10 C1 C8 N3 174.9(3) . . . . ? N1 C1 C8 S1 120.7(2) . . . . ? N2 C1 C8 S1 -124.7(2) . . . . ? C10 C1 C8 S1 -3.2(3) . . . . ? C31 C9 C10 C33 -0.7(5) . . . . ? S1 C9 C10 C33 -178.2(3) . . . . ? C31 C9 C10 C1 177.8(3) . . . . ? S1 C9 C10 C1 0.2(4) . . . . ? N1 C1 C10 C9 -121.5(3) . . . . ? N2 C1 C10 C9 123.5(3) . . . . ? C8 C1 C10 C9 1.9(3) . . . . ? N1 C1 C10 C33 57.1(3) . . . . ? N2 C1 C10 C33 -57.9(4) . . . . ? C8 C1 C10 C33 -179.5(3) . . . . ? N2 C11 C12 C17 -22.1(4) . . . . ? N2 C11 C12 C13 158.6(3) . . . . ? C17 C12 C13 C14 -2.9(5) . . . . ? C11 C12 C13 C14 176.5(3) . . . . ? C12 C13 C14 C15 1.8(5) . . . . ? C13 C14 C15 C16 0.3(6) . . . . ? C14 C15 C16 C17 -1.2(5) . . . . ? C13 C12 C17 C16 2.0(5) . . . . ? C11 C12 C17 C16 -177.4(3) . . . . ? C15 C16 C17 C12 0.0(5) . . . . ? N1 C18 C19 C20 -144.4(3) . . . . ? N1 C18 C19 C24 37.4(4) . . . . ? C24 C19 C20 C21 -0.1(5) . . . . ? C18 C19 C20 C21 -178.4(4) . . . . ? C19 C20 C21 C22 -1.9(7) . . . . ? C20 C21 C22 C23 2.2(7) . . . . ? C21 C22 C23 C24 -0.5(7) . . . . ? C22 C23 C24 C19 -1.5(6) . . . . ? C20 C19 C24 C23 1.8(5) . . . . ? C18 C19 C24 C23 -180.0(3) . . . . ? C30 C25 C26 C27 1.9(6) . . . . ? N3 C25 C26 C27 177.1(3) . . . . ? C25 C26 C27 C28 -2.9(7) . . . . ? C26 C27 C28 C29 2.4(7) . . . . ? C27 C28 C29 C30 -1.0(7) . . . . ? C26 C25 C30 C29 -0.5(5) . . . . ? N3 C25 C30 C29 -175.4(3) . . . . ? C28 C29 C30 C25 0.0(6) . . . . ? C10 C9 C31 O1 -178.7(3) . . . . ? S1 C9 C31 O1 -1.1(4) . . . . ? C10 C9 C31 O2 -0.4(5) . . . . ? S1 C9 C31 O2 177.2(2) . . . . ? C9 C10 C33 O3 100.6(4) . . . . ? C1 C10 C33 O3 -77.9(4) . . . . ? C9 C10 C33 O4 -80.0(4) . . . . ? C1 C10 C33 O4 101.5(3) . . . . ? C41 C36 C37 C38 -2.1(5) . . . . ? N4 C36 C37 C38 177.7(3) . . . . ? C36 C37 C38 C39 -0.1(5) . . . . ? C37 C38 C39 C40 0.9(6) . . . . ? C38 C39 C40 C41 0.5(5) . . . . ? C39 C40 C41 C36 -2.7(5) . . . . ? C39 C40 C41 N5 -179.0(3) . . . . ? C37 C36 C41 C40 3.6(5) . . . . ? N4 C36 C41 C40 -176.2(3) . . . . ? C37 C36 C41 N5 -179.3(3) . . . . ? N4 C36 C41 N5 0.9(3) . . . . ? N5 C35 C42 N6 -62.4(4) . . . . ? N4 C35 C42 N6 52.9(4) . . . . ? C44 C35 C42 N6 174.6(3) . . . . ? N5 C35 C42 S2 119.1(2) . . . . ? N4 C35 C42 S2 -125.6(2) . . . . ? C44 C35 C42 S2 -3.9(3) . . . . ? C65 C43 C44 C67 0.6(6) . . . . ? S2 C43 C44 C67 178.6(3) . . . . ? C65 C43 C44 C35 -178.6(3) . . . . ? S2 C43 C44 C35 -0.5(4) . . . . ? N5 C35 C44 C43 -120.9(3) . . . . ? N4 C35 C44 C43 124.0(3) . . . . ? C42 C35 C44 C43 2.8(4) . . . . ? N5 C35 C44 C67 59.9(4) . . . . ? N4 C35 C44 C67 -55.2(4) . . . . ? C42 C35 C44 C67 -176.4(3) . . . . ? N4 C45 C46 C51 -16.5(5) . . . . ? N4 C45 C46 C47 168.6(3) . . . . ? C51 C46 C47 C48 -1.1(5) . . . . ? C45 C46 C47 C48 174.0(3) . . . . ? C46 C47 C48 C49 0.4(6) . . . . ? C47 C48 C49 C50 0.5(7) . . . . ? C48 C49 C50 C51 -0.6(7) . . . . ? C47 C46 C51 C50 1.0(5) . . . . ? C45 C46 C51 C50 -173.9(3) . . . . ? C49 C50 C51 C46 -0.2(6) . . . . ? N5 C52 C53 C54 34.8(5) . . . . ? N5 C52 C53 C58 -148.4(3) . . . . ? C58 C53 C54 C55 1.5(5) . . . . ? C52 C53 C54 C55 178.2(3) . . . . ? C53 C54 C55 C56 -0.9(6) . . . . ? C54 C55 C56 C57 -0.2(6) . . . . ? C55 C56 C57 C58 0.7(6) . . . . ? C56 C57 C58 C53 -0.1(6) . . . . ? C54 C53 C58 C57 -1.0(5) . . . . ? C52 C53 C58 C57 -177.8(3) . . . . ? C64 C59 C60 C61 -0.5(9) . . . . ? N6 C59 C60 C61 -179.4(5) . . . . ? C59 C60 C61 C62 -0.6(10) . . . . ? C60 C61 C62 C63 0.1(9) . . . . ? C61 C62 C63 C64 1.3(8) . . . . ? C60 C59 C64 C63 1.9(7) . . . . ? N6 C59 C64 C63 -179.2(4) . . . . ? C62 C63 C64 C59 -2.4(7) . . . . ? C44 C43 C65 O5 -10.2(6) . . . . ? S2 C43 C65 O5 171.8(4) . . . . ? C44 C43 C65 O6 167.7(3) . . . . ? S2 C43 C65 O6 -10.3(4) . . . . ? C43 C44 C67 O7 103.7(5) . . . . ? C35 C44 C67 O7 -77.2(5) . . . . ? C43 C44 C67 O8 -80.5(4) . . . . ? C35 C44 C67 O8 98.6(3) . . . . ? C6 C7 N1 C1 -170.1(3) . . . . ? C2 C7 N1 C1 13.2(3) . . . . ? C6 C7 N1 C18 -29.8(5) . . . . ? C2 C7 N1 C18 153.6(3) . . . . ? N2 C1 N1 C7 -20.2(3) . . . . ? C10 C1 N1 C7 -140.9(2) . . . . ? C8 C1 N1 C7 100.1(3) . . . . ? N2 C1 N1 C18 -163.0(2) . . . . ? C10 C1 N1 C18 76.4(3) . . . . ? C8 C1 N1 C18 -42.6(3) . . . . ? C19 C18 N1 C7 63.6(4) . . . . ? C19 C18 N1 C1 -159.2(2) . . . . ? C3 C2 N2 C11 30.3(4) . . . . ? C7 C2 N2 C11 -152.4(3) . . . . ? C3 C2 N2 C1 169.5(3) . . . . ? C7 C2 N2 C1 -13.2(3) . . . . ? C12 C11 N2 C2 -75.4(3) . . . . ? C12 C11 N2 C1 149.0(2) . . . . ? N1 C1 N2 C2 20.2(3) . . . . ? C10 C1 N2 C2 142.0(3) . . . . ? C8 C1 N2 C2 -100.6(3) . . . . ? N1 C1 N2 C11 161.1(2) . . . . ? C10 C1 N2 C11 -77.1(3) . . . . ? C8 C1 N2 C11 40.3(3) . . . . ? C1 C8 N3 C25 178.7(3) . . . . ? S1 C8 N3 C25 -3.5(5) . . . . ? C30 C25 N3 C8 -51.1(5) . . . . ? C26 C25 N3 C8 133.9(3) . . . . ? C37 C36 N4 C45 24.9(5) . . . . ? C41 C36 N4 C45 -155.4(3) . . . . ? C37 C36 N4 C35 165.4(3) . . . . ? C41 C36 N4 C35 -14.8(3) . . . . ? C46 C45 N4 C36 -80.5(4) . . . . ? C46 C45 N4 C35 143.1(3) . . . . ? N5 C35 N4 C36 22.1(3) . . . . ? C44 C35 N4 C36 142.8(3) . . . . ? C42 C35 N4 C36 -99.6(3) . . . . ? N5 C35 N4 C45 164.1(3) . . . . ? C44 C35 N4 C45 -75.1(4) . . . . ? C42 C35 N4 C45 42.4(4) . . . . ? C40 C41 N5 C35 -169.7(3) . . . . ? C36 C41 N5 C35 13.6(3) . . . . ? C40 C41 N5 C52 -32.5(5) . . . . ? C36 C41 N5 C52 150.8(3) . . . . ? N4 C35 N5 C41 -21.6(3) . . . . ? C44 C35 N5 C41 -142.3(2) . . . . ? C42 C35 N5 C41 98.7(3) . . . . ? N4 C35 N5 C52 -161.4(3) . . . . ? C44 C35 N5 C52 77.9(3) . . . . ? C42 C35 N5 C52 -41.1(4) . . . . ? C53 C52 N5 C41 71.8(4) . . . . ? C53 C52 N5 C35 -154.2(3) . . . . ? C35 C42 N6 C59 -178.0(3) . . . . ? S2 C42 N6 C59 0.3(5) . . . . ? C64 C59 N6 C42 99.1(4) . . . . ? C60 C59 N6 C42 -82.0(5) . . . . ? O1 C31 O2 C32 0.3(5) . . . . ? C9 C31 O2 C32 -177.8(3) . . . . ? O3 C33 O4 C34 -4.3(5) . . . . ? C10 C33 O4 C34 176.3(3) . . . . ? O5 C65 O6 C66 2.9(6) . . . . ? C43 C65 O6 C66 -175.0(3) . . . . ? O7 C67 O8 C68 0.2(6) . . . . ? C44 C67 O8 C68 -175.6(3) . . . . ? C10 C9 S1 C8 -1.9(3) . . . . ? C31 C9 S1 C8 -179.8(2) . . . . ? N3 C8 S1 C9 -174.9(3) . . . . ? C1 C8 S1 C9 3.0(2) . . . . ? C44 C43 S2 C42 -1.7(3) . . . . ? C65 C43 S2 C42 176.5(3) . . . . ? N6 C42 S2 C43 -175.1(3) . . . . ? C35 C42 S2 C43 3.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.238 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.042 # Attachment '4b-Y. Cheng.cif' data_50415b _database_code_depnum_ccdc_archive 'CCDC 286159' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Dimethyl 1,3-dibutyl-1'-phenyl-2',3'- dihydrospiro(benzimidazoline-2,3'-pyrrole)-2'-thione-4',5'-dicarboxylate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H33 N3 O4 S' _chemical_formula_weight 507.63 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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' _cell_length_a 10.1747(18) _cell_length_b 20.817(4) _cell_length_c 13.993(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.821(3) _cell_angle_gamma 90.00 _cell_volume 2805.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 4208 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 23.62 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.152 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.942 _exptl_absorpt_correction_T_max 0.964 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 15800 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 26.50 _reflns_number_total 5760 _reflns_number_gt 3358 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+1.2864P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0260(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5760 _refine_ls_number_parameters 328 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.1032 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1683 _refine_ls_wR_factor_gt 0.1351 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.06628(7) 1.04773(4) 0.23007(6) 0.0609(3) Uani 1 1 d . . . N1 N 0.3380(2) 1.02198(9) 0.29057(16) 0.0456(5) Uani 1 1 d . . . N2 N 0.1200(2) 0.89280(10) 0.28625(15) 0.0476(5) Uani 1 1 d . . . N3 N 0.1407(2) 0.91122(10) 0.13243(15) 0.0476(5) Uani 1 1 d . . . O1 O 0.5550(2) 0.84607(10) 0.3122(2) 0.0803(7) Uani 1 1 d . . . O2 O 0.3437(2) 0.80301(9) 0.25922(17) 0.0736(6) Uani 1 1 d . . . O3 O 0.6552(2) 0.98973(12) 0.41516(18) 0.0868(7) Uani 1 1 d . . . O4 O 0.61421(19) 0.98855(10) 0.24758(17) 0.0686(6) Uani 1 1 d . . . C1 C 0.2030(2) 1.00248(12) 0.25514(19) 0.0443(6) Uani 1 1 d . . . C2 C 0.2052(2) 0.92738(12) 0.23849(18) 0.0426(6) Uani 1 1 d . . . C3 C 0.3598(2) 0.91366(12) 0.27746(19) 0.0441(6) Uani 1 1 d . . . C4 C 0.4283(2) 0.96924(12) 0.30168(19) 0.0432(6) Uani 1 1 d . . . C5 C -0.0056(2) 0.87702(11) 0.2136(2) 0.0446(6) Uani 1 1 d . . . C6 C 0.0061(2) 0.88887(11) 0.1185(2) 0.0453(6) Uani 1 1 d . . . C7 C -0.1016(3) 0.87621(13) 0.0320(2) 0.0592(7) Uani 1 1 d . . . H7 H -0.0936 0.8834 -0.0315 0.071 Uiso 1 1 calc R . . C8 C -0.2246(3) 0.85192(15) 0.0434(3) 0.0738(9) Uani 1 1 d . . . H8 H -0.2994 0.8429 -0.0140 0.089 Uiso 1 1 calc R . . C9 C -0.2371(3) 0.84126(15) 0.1354(3) 0.0719(9) Uani 1 1 d . . . H9 H -0.3205 0.8256 0.1399 0.086 Uiso 1 1 calc R . . C10 C -0.1270(3) 0.85338(13) 0.2238(2) 0.0574(7) Uani 1 1 d . . . H10 H -0.1354 0.8458 0.2871 0.069 Uiso 1 1 calc R . . C11 C 0.3832(2) 1.08707(11) 0.3162(2) 0.0458(6) Uani 1 1 d . . . C12 C 0.4272(3) 1.12320(14) 0.2504(2) 0.0621(8) Uani 1 1 d . . . H12 H 0.4284 1.1058 0.1895 0.075 Uiso 1 1 calc R . . C13 C 0.4697(4) 1.18576(16) 0.2754(3) 0.0798(10) Uani 1 1 d . . . H13 H 0.4992 1.2106 0.2310 0.096 Uiso 1 1 calc R . . C14 C 0.4687(4) 1.21119(15) 0.3648(3) 0.0805(10) Uani 1 1 d . . . H14 H 0.4981 1.2532 0.3815 0.097 Uiso 1 1 calc R . . C15 C 0.4245(4) 1.17497(17) 0.4297(3) 0.0806(10) Uani 1 1 d . . . H15 H 0.4233 1.1926 0.4905 0.097 Uiso 1 1 calc R . . C16 C 0.3812(3) 1.11216(14) 0.4058(2) 0.0656(8) Uani 1 1 d . . . H16 H 0.3513 1.0875 0.4502 0.079 Uiso 1 1 calc R . . C17 C 0.4314(3) 0.85160(13) 0.2845(2) 0.0517(7) Uani 1 1 d . . . C18 C 0.4043(4) 0.73975(15) 0.2677(4) 0.1053(14) Uani 1 1 d . . . H18A H 0.4726 0.7390 0.2338 0.158 Uiso 1 1 calc R . . H18B H 0.3330 0.7089 0.2373 0.158 Uiso 1 1 calc R . . H18C H 0.4476 0.7293 0.3377 0.158 Uiso 1 1 calc R . . C19 C 0.5815(3) 0.98265(13) 0.3311(2) 0.0543(7) Uani 1 1 d . . . C20 C 0.7574(3) 1.00440(18) 0.2591(3) 0.0957(13) Uani 1 1 d . . . H20A H 0.7682 1.0502 0.2602 0.144 Uiso 1 1 calc R . . H20B H 0.7816 0.9868 0.2036 0.144 Uiso 1 1 calc R . . H20C H 0.8172 0.9866 0.3213 0.144 Uiso 1 1 calc R . . C21 C 0.1377(3) 0.90108(14) 0.3922(2) 0.0581(7) Uani 1 1 d . . . H21A H 0.0580 0.9238 0.3989 0.070 Uiso 1 1 calc R . . H21B H 0.2193 0.9273 0.4228 0.070 Uiso 1 1 calc R . . C22 C 0.1536(4) 0.83778(17) 0.4484(2) 0.0795(10) Uani 1 1 d . . . H22A H 0.0791 0.8092 0.4119 0.095 Uiso 1 1 calc R . . H22B H 0.2407 0.8180 0.4501 0.095 Uiso 1 1 calc R . . C23 C 0.1514(6) 0.8451(2) 0.5546(3) 0.1195(16) Uani 1 1 d U . . H23A H 0.1823 0.8053 0.5908 0.143 Uiso 1 1 calc R . . H23B H 0.2166 0.8785 0.5880 0.143 Uiso 1 1 calc R . . C24 C 0.0131(7) 0.8616(3) 0.5604(5) 0.172(3) Uani 1 1 d U . . H24A H 0.0201 0.8693 0.6295 0.259 Uiso 1 1 calc R . . H24B H -0.0498 0.8266 0.5343 0.259 Uiso 1 1 calc R . . H24C H -0.0208 0.8995 0.5213 0.259 Uiso 1 1 calc R . . C25 C 0.1831(3) 0.94316(14) 0.0546(2) 0.0600(7) Uani 1 1 d . . . H25A H 0.2265 0.9837 0.0813 0.072 Uiso 1 1 calc R . . H25B H 0.1008 0.9527 -0.0020 0.072 Uiso 1 1 calc R . . C26 C 0.2816(4) 0.9055(2) 0.0168(3) 0.0962(12) Uani 1 1 d . . . H26A H 0.3077 0.9317 -0.0315 0.115 Uiso 1 1 calc R . . H26B H 0.3652 0.8973 0.0732 0.115 Uiso 1 1 calc R . . C27 C 0.2297(5) 0.8455(2) -0.0299(4) 0.1202(15) Uani 1 1 d U . . H27A H 0.1444 0.8535 -0.0848 0.144 Uiso 1 1 calc R . . H27B H 0.2069 0.8186 0.0192 0.144 Uiso 1 1 calc R . . C28 C 0.3303(6) 0.8079(3) -0.0722(4) 0.155(2) Uani 1 1 d U . . H28A H 0.2830 0.7714 -0.1097 0.233 Uiso 1 1 calc R . . H28B H 0.4089 0.7936 -0.0173 0.233 Uiso 1 1 calc R . . H28C H 0.3613 0.8354 -0.1157 0.233 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 0.0422(4) 0.0532(4) 0.0881(6) -0.0001(4) 0.0221(4) 0.0041(3) N1 0.0390(11) 0.0370(11) 0.0599(13) 0.0019(10) 0.0147(10) -0.0041(9) N2 0.0448(12) 0.0514(13) 0.0464(12) -0.0001(10) 0.0144(10) -0.0126(10) N3 0.0462(12) 0.0496(13) 0.0472(12) 0.0011(10) 0.0152(10) -0.0060(10) O1 0.0476(13) 0.0585(13) 0.128(2) 0.0100(13) 0.0191(12) 0.0078(10) O2 0.0589(12) 0.0391(11) 0.1114(18) -0.0072(11) 0.0116(12) 0.0008(9) O3 0.0576(13) 0.0975(18) 0.0841(17) 0.0216(14) -0.0065(12) -0.0198(12) O4 0.0460(11) 0.0733(14) 0.0955(16) 0.0017(12) 0.0354(11) -0.0048(10) C1 0.0390(13) 0.0467(15) 0.0488(15) 0.0021(11) 0.0162(11) -0.0046(11) C2 0.0365(13) 0.0419(14) 0.0495(15) 0.0016(11) 0.0141(11) -0.0041(10) C3 0.0396(13) 0.0434(14) 0.0496(15) 0.0032(11) 0.0146(11) -0.0019(11) C4 0.0367(13) 0.0416(14) 0.0507(15) 0.0062(11) 0.0134(11) -0.0018(10) C5 0.0405(14) 0.0326(13) 0.0595(17) -0.0028(11) 0.0145(12) -0.0029(10) C6 0.0388(13) 0.0353(13) 0.0569(16) -0.0004(11) 0.0087(12) 0.0005(10) C7 0.0573(17) 0.0508(17) 0.0597(18) 0.0029(13) 0.0053(14) 0.0000(13) C8 0.0474(17) 0.070(2) 0.084(2) -0.0005(18) -0.0070(16) -0.0090(15) C9 0.0445(17) 0.069(2) 0.096(3) -0.0017(18) 0.0138(17) -0.0130(14) C10 0.0494(16) 0.0477(16) 0.078(2) -0.0020(14) 0.0243(15) -0.0087(12) C11 0.0414(14) 0.0382(14) 0.0553(16) 0.0039(12) 0.0118(12) -0.0019(10) C12 0.075(2) 0.0488(17) 0.0702(19) 0.0060(14) 0.0342(16) -0.0033(14) C13 0.098(3) 0.0507(19) 0.100(3) 0.0155(18) 0.044(2) -0.0152(17) C14 0.087(2) 0.0424(18) 0.102(3) -0.0020(18) 0.017(2) -0.0130(16) C15 0.103(3) 0.064(2) 0.067(2) -0.0148(17) 0.0163(19) -0.0046(19) C16 0.086(2) 0.0550(18) 0.0555(18) 0.0023(14) 0.0221(16) -0.0111(16) C17 0.0488(16) 0.0445(15) 0.0599(17) 0.0050(12) 0.0151(13) 0.0005(12) C18 0.092(3) 0.0440(19) 0.162(4) -0.010(2) 0.015(3) 0.0115(18) C19 0.0393(14) 0.0419(15) 0.074(2) 0.0113(14) 0.0082(15) -0.0011(11) C20 0.0526(19) 0.082(3) 0.169(4) -0.008(2) 0.059(2) -0.0104(17) C21 0.0588(17) 0.0614(18) 0.0571(18) -0.0051(14) 0.0230(14) -0.0133(14) C22 0.097(3) 0.079(2) 0.066(2) 0.0094(17) 0.0309(19) 0.0015(19) C23 0.171(4) 0.115(3) 0.077(3) 0.005(2) 0.047(3) -0.015(3) C24 0.214(6) 0.193(6) 0.165(5) -0.036(4) 0.137(5) -0.044(4) C25 0.0672(18) 0.0603(18) 0.0554(17) 0.0064(14) 0.0237(14) -0.0067(14) C26 0.112(3) 0.109(3) 0.084(3) 0.010(2) 0.054(2) -0.003(3) C27 0.134(4) 0.114(4) 0.125(4) -0.013(3) 0.059(3) 0.002(3) C28 0.165(5) 0.160(5) 0.162(5) -0.029(4) 0.083(4) 0.048(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 1.622(3) . ? N1 C1 1.363(3) . ? N1 C4 1.408(3) . ? N1 C11 1.439(3) . ? N2 C5 1.391(3) . ? N2 C21 1.444(3) . ? N2 C2 1.446(3) . ? N3 C6 1.399(3) . ? N3 C25 1.455(3) . ? N3 C2 1.455(3) . ? O1 C17 1.196(3) . ? O2 C17 1.319(3) . ? O2 C18 1.443(4) . ? O3 C19 1.182(3) . ? O4 C19 1.321(3) . ? O4 C20 1.451(3) . ? C1 C2 1.582(3) . ? C2 C3 1.516(3) . ? C3 C4 1.337(3) . ? C3 C17 1.470(3) . ? C4 C19 1.504(3) . ? C5 C10 1.379(4) . ? C5 C6 1.397(4) . ? C6 C7 1.370(4) . ? C7 C8 1.406(4) . ? C7 H7 0.9300 . ? C8 C9 1.352(5) . ? C8 H8 0.9300 . ? C9 C10 1.399(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C16 1.364(4) . ? C11 C12 1.371(4) . ? C12 C13 1.381(4) . ? C12 H12 0.9300 . ? C13 C14 1.361(5) . ? C13 H13 0.9300 . ? C14 C15 1.364(5) . ? C14 H14 0.9300 . ? C15 C16 1.386(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.517(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.501(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.475(7) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.498(5) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.429(6) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.550(6) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? 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 N1 C4 110.7(2) . . ? C1 N1 C11 125.1(2) . . ? C4 N1 C11 124.19(19) . . ? C5 N2 C21 124.0(2) . . ? C5 N2 C2 109.04(19) . . ? C21 N2 C2 121.3(2) . . ? C6 N3 C25 124.1(2) . . ? C6 N3 C2 108.59(19) . . ? C25 N3 C2 120.8(2) . . ? C17 O2 C18 116.4(2) . . ? C19 O4 C20 117.0(3) . . ? N1 C1 C2 106.70(19) . . ? N1 C1 S1 126.8(2) . . ? C2 C1 S1 126.45(17) . . ? N2 C2 N3 102.46(18) . . ? N2 C2 C3 116.6(2) . . ? N3 C2 C3 113.4(2) . . ? N2 C2 C1 112.63(19) . . ? N3 C2 C1 110.82(19) . . ? C3 C2 C1 101.28(18) . . ? C4 C3 C17 122.5(2) . . ? C4 C3 C2 108.9(2) . . ? C17 C3 C2 128.6(2) . . ? C3 C4 N1 112.2(2) . . ? C3 C4 C19 129.8(2) . . ? N1 C4 C19 117.9(2) . . ? C10 C5 N2 130.6(3) . . ? C10 C5 C6 121.1(2) . . ? N2 C5 C6 108.3(2) . . ? C7 C6 C5 121.2(2) . . ? C7 C6 N3 130.9(3) . . ? C5 C6 N3 107.8(2) . . ? C6 C7 C8 117.2(3) . . ? C6 C7 H7 121.4 . . ? C8 C7 H7 121.4 . . ? C9 C8 C7 121.9(3) . . ? C9 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? C8 C9 C10 121.2(3) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C5 C10 C9 117.4(3) . . ? C5 C10 H10 121.3 . . ? C9 C10 H10 121.3 . . ? C16 C11 C12 120.8(3) . . ? C16 C11 N1 119.4(2) . . ? C12 C11 N1 119.8(2) . . ? C11 C12 C13 119.3(3) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C14 C13 C12 120.3(3) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 119.9(3) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C16 120.5(3) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C11 C16 C15 119.1(3) . . ? C11 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? O1 C17 O2 124.2(3) . . ? O1 C17 C3 123.5(2) . . ? O2 C17 C3 112.2(2) . . ? O2 C18 H18A 109.5 . . ? O2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O3 C19 O4 127.5(3) . . ? O3 C19 C4 124.4(3) . . ? O4 C19 C4 108.0(2) . . ? O4 C20 H20A 109.5 . . ? O4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N2 C21 C22 112.7(2) . . ? N2 C21 H21A 109.0 . . ? C22 C21 H21A 109.0 . . ? N2 C21 H21B 109.0 . . ? C22 C21 H21B 109.0 . . ? H21A C21 H21B 107.8 . . ? C23 C22 C21 113.1(3) . . ? C23 C22 H22A 109.0 . . ? C21 C22 H22A 109.0 . . ? C23 C22 H22B 109.0 . . ? C21 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? C24 C23 C22 113.5(4) . . ? C24 C23 H23A 108.9 . . ? C22 C23 H23A 108.9 . . ? C24 C23 H23B 108.9 . . ? C22 C23 H23B 108.9 . . ? H23A C23 H23B 107.7 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N3 C25 C26 114.8(3) . . ? N3 C25 H25A 108.6 . . ? C26 C25 H25A 108.6 . . ? N3 C25 H25B 108.6 . . ? C26 C25 H25B 108.6 . . ? H25A C25 H25B 107.6 . . ? C27 C26 C25 115.4(4) . . ? C27 C26 H26A 108.4 . . ? C25 C26 H26A 108.4 . . ? C27 C26 H26B 108.4 . . ? C25 C26 H26B 108.4 . . ? H26A C26 H26B 107.5 . . ? C26 C27 C28 115.1(4) . . ? C26 C27 H27A 108.5 . . ? C28 C27 H27A 108.5 . . ? C26 C27 H27B 108.5 . . ? C28 C27 H27B 108.5 . . ? H27A C27 H27B 107.5 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? 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 C4 N1 C1 C2 -1.5(3) . . . . ? C11 N1 C1 C2 -179.7(2) . . . . ? C4 N1 C1 S1 -179.00(19) . . . . ? C11 N1 C1 S1 2.7(4) . . . . ? C5 N2 C2 N3 -18.4(2) . . . . ? C21 N2 C2 N3 -172.9(2) . . . . ? C5 N2 C2 C3 -142.9(2) . . . . ? C21 N2 C2 C3 62.7(3) . . . . ? C5 N2 C2 C1 100.7(2) . . . . ? C21 N2 C2 C1 -53.8(3) . . . . ? C6 N3 C2 N2 18.9(2) . . . . ? C25 N3 C2 N2 171.7(2) . . . . ? C6 N3 C2 C3 145.4(2) . . . . ? C25 N3 C2 C3 -61.8(3) . . . . ? C6 N3 C2 C1 -101.5(2) . . . . ? C25 N3 C2 C1 51.3(3) . . . . ? N1 C1 C2 N2 128.8(2) . . . . ? S1 C1 C2 N2 -53.7(3) . . . . ? N1 C1 C2 N3 -117.1(2) . . . . ? S1 C1 C2 N3 60.4(3) . . . . ? N1 C1 C2 C3 3.5(2) . . . . ? S1 C1 C2 C3 -178.92(19) . . . . ? N2 C2 C3 C4 -127.1(2) . . . . ? N3 C2 C3 C4 114.3(2) . . . . ? C1 C2 C3 C4 -4.5(3) . . . . ? N2 C2 C3 C17 56.2(3) . . . . ? N3 C2 C3 C17 -62.5(3) . . . . ? C1 C2 C3 C17 178.8(2) . . . . ? C17 C3 C4 N1 -179.0(2) . . . . ? C2 C3 C4 N1 4.1(3) . . . . ? C17 C3 C4 C19 5.4(4) . . . . ? C2 C3 C4 C19 -171.5(3) . . . . ? C1 N1 C4 C3 -1.6(3) . . . . ? C11 N1 C4 C3 176.7(2) . . . . ? C1 N1 C4 C19 174.6(2) . . . . ? C11 N1 C4 C19 -7.1(4) . . . . ? C21 N2 C5 C10 -15.1(4) . . . . ? C2 N2 C5 C10 -168.7(3) . . . . ? C21 N2 C5 C6 165.1(2) . . . . ? C2 N2 C5 C6 11.5(3) . . . . ? C10 C5 C6 C7 -1.3(4) . . . . ? N2 C5 C6 C7 178.5(2) . . . . ? C10 C5 C6 N3 -178.9(2) . . . . ? N2 C5 C6 N3 0.9(3) . . . . ? C25 N3 C6 C7 18.2(4) . . . . ? C2 N3 C6 C7 169.9(3) . . . . ? C25 N3 C6 C5 -164.5(2) . . . . ? C2 N3 C6 C5 -12.8(3) . . . . ? C5 C6 C7 C8 1.1(4) . . . . ? N3 C6 C7 C8 178.0(3) . . . . ? C6 C7 C8 C9 -0.1(5) . . . . ? C7 C8 C9 C10 -0.7(5) . . . . ? N2 C5 C10 C9 -179.2(3) . . . . ? C6 C5 C10 C9 0.6(4) . . . . ? C8 C9 C10 C5 0.4(5) . . . . ? C1 N1 C11 C16 78.1(3) . . . . ? C4 N1 C11 C16 -99.9(3) . . . . ? C1 N1 C11 C12 -101.6(3) . . . . ? C4 N1 C11 C12 80.4(3) . . . . ? C16 C11 C12 C13 -0.1(4) . . . . ? N1 C11 C12 C13 179.6(3) . . . . ? C11 C12 C13 C14 0.4(5) . . . . ? C12 C13 C14 C15 -0.5(6) . . . . ? C13 C14 C15 C16 0.4(6) . . . . ? C12 C11 C16 C15 0.0(4) . . . . ? N1 C11 C16 C15 -179.7(3) . . . . ? C14 C15 C16 C11 -0.1(5) . . . . ? C18 O2 C17 O1 0.9(5) . . . . ? C18 O2 C17 C3 -177.6(3) . . . . ? C4 C3 C17 O1 0.1(4) . . . . ? C2 C3 C17 O1 176.4(3) . . . . ? C4 C3 C17 O2 178.5(2) . . . . ? C2 C3 C17 O2 -5.2(4) . . . . ? C20 O4 C19 O3 1.2(4) . . . . ? C20 O4 C19 C4 177.5(2) . . . . ? C3 C4 C19 O3 -100.0(4) . . . . ? N1 C4 C19 O3 84.6(3) . . . . ? C3 C4 C19 O4 83.6(3) . . . . ? N1 C4 C19 O4 -91.9(3) . . . . ? C5 N2 C21 C22 80.8(3) . . . . ? C2 N2 C21 C22 -128.7(3) . . . . ? N2 C21 C22 C23 -171.7(3) . . . . ? C21 C22 C23 C24 71.1(5) . . . . ? C6 N3 C25 C26 -111.7(3) . . . . ? C2 N3 C25 C26 99.8(3) . . . . ? N3 C25 C26 C27 61.5(5) . . . . ? C25 C26 C27 C28 177.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.567 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.044 # Attachment 'Revised-5c-Y. Cheng.cif' data_a _database_code_depnum_ccdc_archive 'CCDC 286160' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 1,3-di-tert-butyl-2'-phenylimino-2',3'- dihydrospiro(imidazolidine-2,3'-thiophene)-4',5'-dicarboxylate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H33 N3 O4 S' _chemical_formula_weight 459.59 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.097(2) _cell_length_b 10.422(2) _cell_length_c 13.951(3) _cell_angle_alpha 73.04(3) _cell_angle_beta 69.53(3) _cell_angle_gamma 66.32(3) _cell_volume 1239.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 492 _exptl_absorpt_coefficient_mu 0.164 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9025 _exptl_absorpt_correction_T_max 0.9398 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5630 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5630 _reflns_number_gt 4121 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0972P)^2^+0.4851P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5630 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0894 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.1905 _refine_ls_wR_factor_gt 0.1742 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.28314(8) -0.00847(6) 0.13854(5) 0.0490(2) Uani 1 1 d . . . O1 O 0.5669(3) -0.1549(3) 0.3835(2) 0.0937(8) Uani 1 1 d . . . O2 O 0.3363(3) -0.1230(3) 0.48288(14) 0.0735(6) Uani 1 1 d . . . O3 O 0.3530(3) 0.1619(2) 0.32524(17) 0.0824(7) Uani 1 1 d . . . O4 O 0.2761(3) 0.24523(19) 0.18133(15) 0.0659(5) Uani 1 1 d . . . N1 N 0.5169(3) -0.3644(2) 0.27487(16) 0.0535(5) Uani 1 1 d . . . N2 N 0.2730(3) -0.3158(2) 0.37204(16) 0.0567(6) Uani 1 1 d . . . N3 N 0.2923(2) -0.2747(2) 0.14366(15) 0.0454(5) Uani 1 1 d . . . C1 C 0.4923(5) -0.4979(3) 0.3271(3) 0.0854(11) Uani 1 1 d . . . H1A H 0.4920 -0.5468 0.2778 0.103 Uiso 1 1 calc R . . H1B H 0.5707 -0.5590 0.3613 0.103 Uiso 1 1 calc R . . C2 C 0.3505(5) -0.4631(4) 0.4014(3) 0.0942(12) Uani 1 1 d . . . H2A H 0.3635 -0.4815 0.4704 0.113 Uiso 1 1 calc R . . H2B H 0.2941 -0.5200 0.4019 0.113 Uiso 1 1 calc R . . C3 C 0.3712(3) -0.2503(2) 0.28427(17) 0.0434(5) Uani 1 1 d . . . C4 C 0.3781(3) -0.1195(2) 0.30747(17) 0.0430(5) Uani 1 1 d . . . C5 C 0.3335(3) 0.0026(2) 0.24408(17) 0.0445(5) Uani 1 1 d . . . C6 C 0.3144(3) -0.1942(2) 0.18410(16) 0.0407(5) Uani 1 1 d . . . C7 C 0.6521(3) -0.3681(3) 0.1869(2) 0.0651(7) Uani 1 1 d . . . C8 C 0.7884(4) -0.4510(5) 0.2314(4) 0.1042(14) Uani 1 1 d . . . H8A H 0.7856 -0.5448 0.2650 0.156 Uiso 1 1 calc R . . H8B H 0.7860 -0.4022 0.2809 0.156 Uiso 1 1 calc R . . H8C H 0.8789 -0.4580 0.1761 0.156 Uiso 1 1 calc R . . C9 C 0.6629(4) -0.2224(4) 0.1369(3) 0.0900(11) Uani 1 1 d . . . H9A H 0.5825 -0.1681 0.1045 0.135 Uiso 1 1 calc R . . H9B H 0.7572 -0.2313 0.0854 0.135 Uiso 1 1 calc R . . H9C H 0.6557 -0.1749 0.1889 0.135 Uiso 1 1 calc R . . C10 C 0.6619(5) -0.4431(5) 0.1032(3) 0.1035(14) Uani 1 1 d . . . H10A H 0.6542 -0.5357 0.1349 0.155 Uiso 1 1 calc R . . H10B H 0.7562 -0.4525 0.0516 0.155 Uiso 1 1 calc R . . H10C H 0.5815 -0.3877 0.0711 0.155 Uiso 1 1 calc R . . C11 C 0.1090(4) -0.2589(4) 0.4125(2) 0.0641(7) Uani 1 1 d . . . C12 C 0.0719(5) -0.2964(5) 0.5309(2) 0.0957(12) Uani 1 1 d . . . H12A H -0.0350 -0.2652 0.5593 0.143 Uiso 1 1 calc R . . H12B H 0.1148 -0.2501 0.5562 0.143 Uiso 1 1 calc R . . H12C H 0.1126 -0.3976 0.5516 0.143 Uiso 1 1 calc R . . C13 C 0.0314(5) -0.3252(6) 0.3734(3) 0.1050(15) Uani 1 1 d . . . H13A H 0.0647 -0.3129 0.2990 0.158 Uiso 1 1 calc R . . H13B H -0.0752 -0.2794 0.3947 0.158 Uiso 1 1 calc R . . H13C H 0.0560 -0.4249 0.4022 0.158 Uiso 1 1 calc R . . C14 C 0.0467(4) -0.0984(4) 0.3849(3) 0.0861(10) Uani 1 1 d . . . H14A H 0.0744 -0.0698 0.3108 0.129 Uiso 1 1 calc R . . H14B H 0.0868 -0.0564 0.4162 0.129 Uiso 1 1 calc R . . H14C H -0.0606 -0.0671 0.4104 0.129 Uiso 1 1 calc R . . C15 C 0.4383(3) -0.1357(3) 0.3955(2) 0.0543(6) Uani 1 1 d . . . C16 C 0.3803(6) -0.1257(5) 0.5711(3) 0.0971(13) Uani 1 1 d . . . H16A H 0.2963 -0.1196 0.6315 0.146 Uiso 1 1 calc R . . H16B H 0.4136 -0.0464 0.5580 0.146 Uiso 1 1 calc R . . H16C H 0.4605 -0.2128 0.5827 0.146 Uiso 1 1 calc R . . C17 C 0.3234(3) 0.1427(3) 0.25643(19) 0.0494(6) Uani 1 1 d . . . C18 C 0.2599(5) 0.3876(3) 0.1868(3) 0.0903(12) Uani 1 1 d . . . H18A H 0.2330 0.4522 0.1263 0.135 Uiso 1 1 calc R . . H18B H 0.3532 0.3885 0.1897 0.135 Uiso 1 1 calc R . . H18C H 0.1830 0.4166 0.2480 0.135 Uiso 1 1 calc R . . C19 C 0.2441(3) -0.2215(2) 0.05110(18) 0.0442(5) Uani 1 1 d . . . C20 C 0.1110(3) -0.2297(3) 0.0521(2) 0.0591(7) Uani 1 1 d . . . H20A H 0.0522 -0.2663 0.1134 0.071 Uiso 1 1 calc R . . C21 C 0.0650(4) -0.1838(4) -0.0374(3) 0.0748(9) Uani 1 1 d . . . H21A H -0.0255 -0.1891 -0.0360 0.090 Uiso 1 1 calc R . . C22 C 0.1497(4) -0.1305(4) -0.1286(2) 0.0709(8) Uani 1 1 d . . . H22A H 0.1169 -0.0993 -0.1886 0.085 Uiso 1 1 calc R . . C23 C 0.2833(4) -0.1234(4) -0.1308(2) 0.0720(9) Uani 1 1 d . . . H23A H 0.3420 -0.0880 -0.1927 0.086 Uiso 1 1 calc R . . C24 C 0.3309(3) -0.1687(4) -0.0412(2) 0.0635(7) Uani 1 1 d . . . H24A H 0.4217 -0.1638 -0.0430 0.076 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 0.0699(4) 0.0409(3) 0.0449(3) -0.0009(2) -0.0303(3) -0.0189(3) O1 0.0758(16) 0.142(2) 0.0898(16) -0.0467(16) -0.0342(13) -0.0336(15) O2 0.0896(15) 0.1063(18) 0.0451(10) -0.0130(10) -0.0252(10) -0.0472(13) O3 0.144(2) 0.0582(12) 0.0764(14) -0.0062(10) -0.0634(14) -0.0394(13) O4 0.1046(16) 0.0389(9) 0.0640(11) -0.0044(8) -0.0401(11) -0.0219(10) N1 0.0643(14) 0.0409(11) 0.0563(12) -0.0017(9) -0.0285(11) -0.0126(10) N2 0.0735(16) 0.0515(12) 0.0457(11) 0.0032(9) -0.0154(10) -0.0302(11) N3 0.0550(12) 0.0455(10) 0.0447(10) -0.0076(8) -0.0201(9) -0.0202(9) C1 0.099(3) 0.0423(15) 0.104(3) 0.0029(16) -0.037(2) -0.0158(16) C2 0.108(3) 0.0563(18) 0.106(3) 0.0195(19) -0.030(2) -0.037(2) C3 0.0571(14) 0.0413(12) 0.0385(11) -0.0026(9) -0.0193(10) -0.0205(10) C4 0.0515(13) 0.0438(12) 0.0409(11) -0.0071(9) -0.0177(10) -0.0188(10) C5 0.0541(14) 0.0444(12) 0.0431(11) -0.0058(9) -0.0196(10) -0.0200(10) C6 0.0471(12) 0.0406(11) 0.0374(10) -0.0044(9) -0.0144(9) -0.0166(9) C7 0.0546(16) 0.0650(17) 0.0655(17) -0.0151(14) -0.0210(13) -0.0031(13) C8 0.071(2) 0.114(3) 0.114(3) -0.008(3) -0.048(2) -0.005(2) C9 0.064(2) 0.087(2) 0.085(2) -0.0002(19) 0.0016(18) -0.0202(18) C10 0.087(3) 0.121(3) 0.092(3) -0.054(2) -0.022(2) 0.000(2) C11 0.0727(19) 0.079(2) 0.0484(14) -0.0111(13) -0.0047(13) -0.0431(16) C12 0.118(3) 0.122(3) 0.0500(17) -0.0118(19) 0.0017(18) -0.065(3) C13 0.093(3) 0.160(4) 0.095(3) -0.048(3) -0.004(2) -0.075(3) C14 0.064(2) 0.087(2) 0.084(2) -0.0118(19) 0.0015(17) -0.0226(18) C15 0.0727(18) 0.0469(13) 0.0550(15) -0.0056(11) -0.0344(14) -0.0191(12) C16 0.159(4) 0.099(3) 0.0628(19) -0.0008(18) -0.056(2) -0.059(3) C17 0.0588(15) 0.0459(13) 0.0488(13) -0.0082(10) -0.0175(11) -0.0202(11) C18 0.151(4) 0.0416(15) 0.087(2) -0.0088(15) -0.049(2) -0.0275(19) C19 0.0513(13) 0.0433(12) 0.0453(12) -0.0106(9) -0.0204(10) -0.0145(10) C20 0.0574(16) 0.0714(18) 0.0549(14) -0.0051(13) -0.0207(12) -0.0272(14) C21 0.0623(18) 0.100(2) 0.0732(19) -0.0076(18) -0.0347(16) -0.0294(17) C22 0.080(2) 0.086(2) 0.0570(16) -0.0078(15) -0.0386(15) -0.0235(17) C23 0.083(2) 0.099(2) 0.0455(14) -0.0060(15) -0.0221(14) -0.0422(19) C24 0.0636(17) 0.090(2) 0.0501(14) -0.0101(14) -0.0179(13) -0.0384(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C5 1.764(2) . ? S1 C6 1.784(2) . ? O1 C15 1.189(3) . ? O2 C15 1.293(4) . ? O2 C16 1.437(3) . ? O3 C17 1.188(3) . ? O4 C17 1.325(3) . ? O4 C18 1.448(3) . ? N1 C1 1.444(4) . ? N1 C3 1.465(3) . ? N1 C7 1.479(4) . ? N2 C2 1.424(4) . ? N2 C3 1.469(3) . ? N2 C11 1.471(4) . ? N3 C6 1.260(3) . ? N3 C19 1.420(3) . ? C1 C2 1.421(5) . ? C3 C4 1.522(3) . ? C3 C6 1.562(3) . ? C4 C5 1.329(3) . ? C4 C15 1.492(3) . ? C5 C17 1.479(3) . ? C7 C9 1.505(5) . ? C7 C8 1.535(4) . ? C7 C10 1.540(5) . ? C11 C14 1.514(5) . ? C11 C12 1.527(4) . ? C11 C13 1.530(5) . ? C19 C20 1.376(4) . ? C19 C24 1.383(4) . ? C20 C21 1.372(4) . ? C21 C22 1.367(5) . ? C22 C23 1.370(4) . ? C23 C24 1.382(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 C5 S1 C6 90.77(11) . . ? C15 O2 C16 117.5(3) . . ? C17 O4 C18 116.2(2) . . ? C1 N1 C3 108.7(2) . . ? C1 N1 C7 117.8(3) . . ? C3 N1 C7 126.0(2) . . ? C2 N2 C3 110.5(2) . . ? C2 N2 C11 119.5(3) . . ? C3 N2 C11 128.4(2) . . ? C6 N3 C19 120.5(2) . . ? C2 C1 N1 106.2(3) . . ? C1 C2 N2 107.2(3) . . ? N1 C3 N2 102.37(19) . . ? N1 C3 C4 110.77(19) . . ? N2 C3 C4 111.67(19) . . ? N1 C3 C6 115.01(19) . . ? N2 C3 C6 112.84(19) . . ? C4 C3 C6 104.41(18) . . ? C5 C4 C15 124.2(2) . . ? C5 C4 C3 116.51(19) . . ? C15 C4 C3 119.2(2) . . ? C4 C5 C17 125.0(2) . . ? C4 C5 S1 115.73(18) . . ? C17 C5 S1 119.28(17) . . ? N3 C6 C3 121.7(2) . . ? N3 C6 S1 125.76(17) . . ? C3 C6 S1 112.49(15) . . ? N1 C7 C9 112.8(2) . . ? N1 C7 C8 107.0(3) . . ? C9 C7 C8 106.5(3) . . ? N1 C7 C10 112.2(3) . . ? C9 C7 C10 109.2(3) . . ? C8 C7 C10 108.9(3) . . ? N2 C11 C14 112.8(2) . . ? N2 C11 C12 107.7(3) . . ? C14 C11 C12 106.8(3) . . ? N2 C11 C13 111.0(3) . . ? C14 C11 C13 109.4(3) . . ? C12 C11 C13 109.0(3) . . ? O1 C15 O2 124.9(2) . . ? O1 C15 C4 122.0(3) . . ? O2 C15 C4 113.1(2) . . ? O3 C17 O4 123.9(2) . . ? O3 C17 C5 124.6(2) . . ? O4 C17 C5 111.5(2) . . ? C20 C19 C24 119.1(2) . . ? C20 C19 N3 118.9(2) . . ? C24 C19 N3 121.9(2) . . ? C21 C20 C19 119.9(3) . . ? C22 C21 C20 121.2(3) . . ? C21 C22 C23 119.4(3) . . ? C22 C23 C24 120.1(3) . . ? C23 C24 C19 120.3(3) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.655 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.057 # Attachment '7c-Y. Cheng.cif' data_50320a _database_code_depnum_ccdc_archive 'CCDC 286161' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Ethyl 1,3-dibenzyl-1'-phenyl-2',3'- dihydrospiro(benzimidazoline-2,3'-pyrrole)-2'-thione-4'-carboxylate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H29 N3 O2 S' _chemical_formula_weight 531.65 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7945(18) _cell_length_b 10.295(2) _cell_length_c 14.282(2) _cell_angle_alpha 70.912(2) _cell_angle_beta 88.222(3) _cell_angle_gamma 89.992(3) _cell_volume 1360.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 1113 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 20.19 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.155 _exptl_absorpt_correction_type MUTLI-SCAN _exptl_absorpt_correction_T_min 0.950 _exptl_absorpt_correction_T_max 0.969 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 7402 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0750 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4731 _reflns_number_gt 2917 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0329P)^2^+0.3909P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4731 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0917 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1184 _refine_ls_wR_factor_gt 0.1023 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.99583(7) 0.61539(8) 0.11193(6) 0.0545(2) Uani 1 1 d . . . N1 N 0.73574(19) 0.57045(19) 0.27617(14) 0.0350(5) Uani 1 1 d . . . N2 N 0.73521(19) 0.39840(19) 0.20908(15) 0.0382(5) Uani 1 1 d . . . N3 N 0.76196(19) 0.7056(2) 0.02201(14) 0.0397(5) Uani 1 1 d . . . O1 O 0.35472(19) 0.5716(2) 0.10600(14) 0.0754(7) Uani 1 1 d . . . O2 O 0.43216(17) 0.5027(2) 0.25874(13) 0.0560(5) Uani 1 1 d . . . C1 C 0.7206(2) 0.5467(2) 0.18155(17) 0.0361(6) Uani 1 1 d . . . C2 C 0.8019(2) 0.4576(2) 0.34039(17) 0.0328(6) Uani 1 1 d . . . C3 C 0.8604(2) 0.4400(3) 0.42926(18) 0.0427(6) Uani 1 1 d . . . H3 H 0.8625 0.5109 0.4562 0.051 Uiso 1 1 calc R . . C4 C 0.9166(3) 0.3124(3) 0.4781(2) 0.0526(7) Uani 1 1 d . . . H4 H 0.9577 0.2982 0.5385 0.063 Uiso 1 1 calc R . . C5 C 0.9125(3) 0.2077(3) 0.4391(2) 0.0587(8) Uani 1 1 d . . . H5 H 0.9501 0.1233 0.4737 0.070 Uiso 1 1 calc R . . C6 C 0.8528(3) 0.2252(3) 0.3482(2) 0.0511(7) Uani 1 1 d . . . H6 H 0.8496 0.1538 0.3218 0.061 Uiso 1 1 calc R . . C7 C 0.7992(2) 0.3511(2) 0.29939(18) 0.0364(6) Uani 1 1 d . . . C8 C 0.8313(2) 0.6269(2) 0.10126(18) 0.0367(6) Uani 1 1 d . . . C9 C 0.6206(2) 0.6830(2) 0.03851(19) 0.0415(6) Uani 1 1 d . . . H9 H 0.5561 0.7236 -0.0084 0.050 Uiso 1 1 calc R . . C10 C 0.5894(2) 0.5972(2) 0.12844(18) 0.0363(6) Uani 1 1 d . . . C11 C 0.7615(2) 0.7085(2) 0.27798(19) 0.0415(6) Uani 1 1 d . . . H11A H 0.7331 0.7739 0.2160 0.050 Uiso 1 1 calc R . . H11B H 0.8591 0.7206 0.2822 0.050 Uiso 1 1 calc R . . C12 C 0.6895(2) 0.7409(2) 0.36242(18) 0.0378(6) Uani 1 1 d . . . C13 C 0.7408(3) 0.8433(3) 0.3946(2) 0.0534(7) Uani 1 1 d . . . H13 H 0.8234 0.8860 0.3678 0.064 Uiso 1 1 calc R . . C14 C 0.6711(3) 0.8830(3) 0.4661(2) 0.0645(9) Uani 1 1 d . . . H14 H 0.7063 0.9532 0.4862 0.077 Uiso 1 1 calc R . . C15 C 0.5514(3) 0.8202(3) 0.5074(2) 0.0633(8) Uani 1 1 d . . . H15 H 0.5047 0.8475 0.5554 0.076 Uiso 1 1 calc R . . C16 C 0.4999(3) 0.7166(3) 0.4780(2) 0.0641(9) Uani 1 1 d . . . H16 H 0.4185 0.6727 0.5065 0.077 Uiso 1 1 calc R . . C17 C 0.5692(3) 0.6771(3) 0.4057(2) 0.0522(7) Uani 1 1 d . . . H17 H 0.5338 0.6065 0.3861 0.063 Uiso 1 1 calc R . . C18 C 0.7577(3) 0.3363(3) 0.13222(19) 0.0454(7) Uani 1 1 d . . . H18A H 0.8533 0.3124 0.1304 0.054 Uiso 1 1 calc R . . H18B H 0.7381 0.4036 0.0686 0.054 Uiso 1 1 calc R . . C19 C 0.6715(2) 0.2089(2) 0.14636(19) 0.0396(6) Uani 1 1 d . . . C20 C 0.5692(3) 0.1665(3) 0.2183(2) 0.0527(7) Uani 1 1 d . . . H20 H 0.5520 0.2158 0.2615 0.063 Uiso 1 1 calc R . . C21 C 0.4915(3) 0.0501(3) 0.2266(3) 0.0660(9) Uani 1 1 d . . . H21 H 0.4236 0.0207 0.2761 0.079 Uiso 1 1 calc R . . C22 C 0.5145(3) -0.0212(3) 0.1620(3) 0.0713(10) Uani 1 1 d . . . H22 H 0.4615 -0.0983 0.1669 0.086 Uiso 1 1 calc R . . C23 C 0.6149(3) 0.0210(3) 0.0908(3) 0.0674(9) Uani 1 1 d . . . H23 H 0.6301 -0.0274 0.0468 0.081 Uiso 1 1 calc R . . C24 C 0.6944(3) 0.1344(3) 0.0826(2) 0.0522(7) Uani 1 1 d . . . H24 H 0.7639 0.1611 0.0341 0.063 Uiso 1 1 calc R . . C25 C 0.8191(2) 0.7988(3) -0.0688(2) 0.0411(6) Uani 1 1 d . . . C26 C 0.8748(3) 0.9208(3) -0.0706(2) 0.0646(9) Uani 1 1 d . . . H26 H 0.8827 0.9420 -0.0125 0.078 Uiso 1 1 calc R . . C27 C 0.9196(4) 1.0132(4) -0.1613(3) 0.0849(12) Uani 1 1 d . . . H27 H 0.9586 1.0967 -0.1639 0.102 Uiso 1 1 calc R . . C28 C 0.9070(3) 0.9825(4) -0.2458(3) 0.0851(12) Uani 1 1 d . . . H28 H 0.9346 1.0460 -0.3064 0.102 Uiso 1 1 calc R . . C29 C 0.8542(4) 0.8597(5) -0.2421(3) 0.0880(12) Uani 1 1 d . . . H29 H 0.8475 0.8382 -0.3002 0.106 Uiso 1 1 calc R . . C30 C 0.8098(3) 0.7655(3) -0.1528(2) 0.0664(9) Uani 1 1 d . . . H30 H 0.7743 0.6806 -0.1503 0.080 Uiso 1 1 calc R . . C31 C 0.4481(3) 0.5563(3) 0.1612(2) 0.0452(7) Uani 1 1 d . . . C32 C 0.2918(3) 0.4764(4) 0.2987(2) 0.0730(10) Uani 1 1 d . . . H32A H 0.2913 0.4062 0.3635 0.088 Uiso 1 1 calc R . . H32B H 0.2379 0.4427 0.2555 0.088 Uiso 1 1 calc R . . C33 C 0.2301(3) 0.6040(5) 0.3073(3) 0.1091(15) Uani 1 1 d . . . H33A H 0.2834 0.6371 0.3503 0.164 Uiso 1 1 calc R . . H33B H 0.1385 0.5847 0.3343 0.164 Uiso 1 1 calc R . . H33C H 0.2285 0.6726 0.2429 0.164 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 0.0360(4) 0.0673(5) 0.0533(5) -0.0101(4) -0.0031(3) 0.0004(3) N1 0.0427(11) 0.0311(11) 0.0321(12) -0.0111(9) -0.0043(9) 0.0002(9) N2 0.0486(12) 0.0341(12) 0.0325(13) -0.0113(10) -0.0038(10) 0.0005(9) N3 0.0364(11) 0.0420(12) 0.0344(13) -0.0041(10) 0.0001(9) -0.0035(9) O1 0.0436(11) 0.1235(19) 0.0448(13) -0.0075(12) -0.0087(10) -0.0168(11) O2 0.0417(10) 0.0774(14) 0.0392(12) -0.0060(10) 0.0025(8) -0.0071(9) C1 0.0384(13) 0.0385(14) 0.0307(15) -0.0102(11) -0.0041(11) 0.0002(11) C2 0.0340(13) 0.0336(14) 0.0291(14) -0.0079(11) -0.0030(10) -0.0004(10) C3 0.0475(15) 0.0438(16) 0.0367(16) -0.0128(13) -0.0052(12) -0.0006(12) C4 0.0595(17) 0.0542(18) 0.0421(17) -0.0114(15) -0.0197(14) 0.0082(14) C5 0.076(2) 0.0415(17) 0.055(2) -0.0081(15) -0.0179(16) 0.0163(14) C6 0.0660(18) 0.0383(16) 0.0508(19) -0.0167(14) -0.0088(15) 0.0090(13) C7 0.0384(13) 0.0362(14) 0.0352(15) -0.0123(12) -0.0022(11) -0.0003(11) C8 0.0382(13) 0.0374(14) 0.0361(15) -0.0140(12) -0.0013(11) -0.0009(11) C9 0.0369(14) 0.0446(15) 0.0411(16) -0.0110(13) -0.0064(12) -0.0010(11) C10 0.0356(13) 0.0405(14) 0.0327(15) -0.0117(12) -0.0027(11) -0.0024(11) C11 0.0444(15) 0.0334(14) 0.0451(17) -0.0110(12) 0.0011(12) -0.0030(11) C12 0.0421(14) 0.0328(14) 0.0386(16) -0.0114(12) -0.0030(12) 0.0025(11) C13 0.0541(17) 0.0453(17) 0.067(2) -0.0277(15) 0.0043(15) -0.0039(13) C14 0.080(2) 0.0533(19) 0.072(2) -0.0363(17) -0.0007(18) -0.0052(16) C15 0.083(2) 0.058(2) 0.054(2) -0.0265(16) 0.0101(17) 0.0080(17) C16 0.0617(19) 0.066(2) 0.065(2) -0.0248(18) 0.0184(16) -0.0117(16) C17 0.0555(17) 0.0532(17) 0.0548(19) -0.0279(15) 0.0067(14) -0.0125(13) C18 0.0547(16) 0.0468(16) 0.0390(16) -0.0201(13) -0.0014(13) -0.0032(13) C19 0.0454(15) 0.0382(15) 0.0364(16) -0.0128(12) -0.0111(12) 0.0040(12) C20 0.0562(17) 0.0525(18) 0.0505(19) -0.0183(14) -0.0026(14) -0.0054(14) C21 0.0573(19) 0.060(2) 0.071(2) -0.0074(18) -0.0045(16) -0.0107(16) C22 0.067(2) 0.0470(19) 0.100(3) -0.021(2) -0.028(2) -0.0064(16) C23 0.077(2) 0.0502(19) 0.087(3) -0.0369(18) -0.022(2) 0.0075(17) C24 0.0579(17) 0.0486(17) 0.0571(19) -0.0264(15) -0.0041(14) 0.0033(14) C25 0.0366(14) 0.0438(16) 0.0378(16) -0.0066(13) 0.0019(11) -0.0007(11) C26 0.074(2) 0.0541(19) 0.061(2) -0.0132(16) 0.0072(16) -0.0196(16) C27 0.086(3) 0.059(2) 0.091(3) 0.000(2) 0.014(2) -0.0274(18) C28 0.062(2) 0.101(3) 0.059(3) 0.018(2) 0.0136(18) -0.007(2) C29 0.091(3) 0.123(3) 0.041(2) -0.017(2) 0.0120(18) -0.018(2) C30 0.077(2) 0.073(2) 0.048(2) -0.0186(17) 0.0102(16) -0.0134(17) C31 0.0434(15) 0.0493(16) 0.0384(17) -0.0083(13) -0.0030(13) -0.0032(12) C32 0.0468(18) 0.101(3) 0.054(2) -0.0022(19) 0.0058(15) -0.0112(17) C33 0.059(2) 0.195(5) 0.110(3) -0.100(3) 0.000(2) -0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C8 1.624(2) . ? N1 C2 1.397(3) . ? N1 C11 1.452(3) . ? N1 C1 1.462(3) . ? N2 C7 1.390(3) . ? N2 C18 1.451(3) . ? N2 C1 1.455(3) . ? N3 C8 1.359(3) . ? N3 C9 1.404(3) . ? N3 C25 1.434(3) . ? O1 C31 1.202(3) . ? O2 C31 1.325(3) . ? O2 C32 1.463(3) . ? C1 C10 1.517(3) . ? C1 C8 1.573(3) . ? C2 C3 1.366(3) . ? C2 C7 1.402(3) . ? C3 C4 1.393(3) . ? C3 H3 0.9300 . ? C4 C5 1.367(4) . ? C4 H4 0.9300 . ? C5 C6 1.398(4) . ? C5 H5 0.9300 . ? C6 C7 1.369(3) . ? C6 H6 0.9300 . ? C9 C10 1.325(3) . ? C9 H9 0.9300 . ? C10 C31 1.464(3) . ? C11 C12 1.508(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C17 1.375(3) . ? C12 C13 1.381(3) . ? C13 C14 1.381(4) . ? C13 H13 0.9300 . ? C14 C15 1.360(4) . ? C14 H14 0.9300 . ? C15 C16 1.369(4) . ? C15 H15 0.9300 . ? C16 C17 1.387(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.513(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.376(3) . ? C19 C24 1.382(4) . ? C20 C21 1.389(4) . ? C20 H20 0.9300 . ? C21 C22 1.368(5) . ? C21 H21 0.9300 . ? C22 C23 1.356(4) . ? C22 H22 0.9300 . ? C23 C24 1.375(4) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C30 1.357(4) . ? C25 C26 1.362(4) . ? C26 C27 1.390(4) . ? C26 H26 0.9300 . ? C27 C28 1.352(5) . ? C27 H27 0.9300 . ? C28 C29 1.351(5) . ? C28 H28 0.9300 . ? C29 C30 1.383(4) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C32 C33 1.485(5) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? 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 C2 N1 C11 120.8(2) . . ? C2 N1 C1 108.35(19) . . ? C11 N1 C1 119.97(19) . . ? C7 N2 C18 122.2(2) . . ? C7 N2 C1 108.63(19) . . ? C18 N2 C1 119.51(19) . . ? C8 N3 C9 110.80(19) . . ? C8 N3 C25 127.03(19) . . ? C9 N3 C25 122.16(19) . . ? C31 O2 C32 116.7(2) . . ? N2 C1 N1 102.38(18) . . ? N2 C1 C10 112.62(19) . . ? N1 C1 C10 116.1(2) . . ? N2 C1 C8 112.32(19) . . ? N1 C1 C8 112.35(19) . . ? C10 C1 C8 101.46(18) . . ? C3 C2 N1 130.9(2) . . ? C3 C2 C7 121.2(2) . . ? N1 C2 C7 107.9(2) . . ? C2 C3 C4 117.7(2) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? C5 C4 C3 121.3(3) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 121.2(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C7 C6 C5 117.7(3) . . ? C7 C6 H6 121.2 . . ? C5 C6 H6 121.2 . . ? C6 C7 N2 130.5(2) . . ? C6 C7 C2 120.9(2) . . ? N2 C7 C2 108.5(2) . . ? N3 C8 C1 106.49(18) . . ? N3 C8 S1 127.33(18) . . ? C1 C8 S1 126.18(18) . . ? C10 C9 N3 112.4(2) . . ? C10 C9 H9 123.8 . . ? N3 C9 H9 123.8 . . ? C9 C10 C31 121.8(2) . . ? C9 C10 C1 108.8(2) . . ? C31 C10 C1 129.2(2) . . ? N1 C11 C12 114.3(2) . . ? N1 C11 H11A 108.7 . . ? C12 C11 H11A 108.7 . . ? N1 C11 H11B 108.7 . . ? C12 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C17 C12 C13 118.1(3) . . ? C17 C12 C11 122.3(2) . . ? C13 C12 C11 119.5(2) . . ? C12 C13 C14 120.8(3) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C15 C14 C13 120.5(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 119.7(3) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C15 C16 C17 120.0(3) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C12 C17 C16 120.9(3) . . ? C12 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? N2 C18 C19 113.9(2) . . ? N2 C18 H18A 108.8 . . ? C19 C18 H18A 108.8 . . ? N2 C18 H18B 108.8 . . ? C19 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C20 C19 C24 118.8(2) . . ? C20 C19 C18 122.7(2) . . ? C24 C19 C18 118.5(2) . . ? C19 C20 C21 120.2(3) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C22 C21 C20 120.2(3) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C23 C22 C21 119.6(3) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C22 C23 C24 121.0(3) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C23 C24 C19 120.2(3) . . ? C23 C24 H24 119.9 . . ? C19 C24 H24 119.9 . . ? C30 C25 C26 121.3(3) . . ? C30 C25 N3 118.5(2) . . ? C26 C25 N3 120.2(3) . . ? C25 C26 C27 118.6(3) . . ? C25 C26 H26 120.7 . . ? C27 C26 H26 120.7 . . ? C28 C27 C26 120.5(3) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C29 C28 C27 120.0(3) . . ? C29 C28 H28 120.0 . . ? C27 C28 H28 120.0 . . ? C28 C29 C30 120.7(4) . . ? C28 C29 H29 119.7 . . ? C30 C29 H29 119.7 . . ? C25 C30 C29 118.9(3) . . ? C25 C30 H30 120.5 . . ? C29 C30 H30 120.5 . . ? O1 C31 O2 122.8(2) . . ? O1 C31 C10 124.0(2) . . ? O2 C31 C10 113.1(2) . . ? O2 C32 C33 110.6(3) . . ? O2 C32 H32A 109.5 . . ? C33 C32 H32A 109.5 . . ? O2 C32 H32B 109.5 . . ? C33 C32 H32B 109.5 . . ? H32A C32 H32B 108.1 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? 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 C7 N2 C1 N1 -19.2(2) . . . . ? C18 N2 C1 N1 -165.92(19) . . . . ? C7 N2 C1 C10 -144.6(2) . . . . ? C18 N2 C1 C10 68.6(3) . . . . ? C7 N2 C1 C8 101.6(2) . . . . ? C18 N2 C1 C8 -45.2(3) . . . . ? C2 N1 C1 N2 20.1(2) . . . . ? C11 N1 C1 N2 164.70(19) . . . . ? C2 N1 C1 C10 143.26(19) . . . . ? C11 N1 C1 C10 -72.2(3) . . . . ? C2 N1 C1 C8 -100.6(2) . . . . ? C11 N1 C1 C8 44.0(3) . . . . ? C11 N1 C2 C3 22.9(4) . . . . ? C1 N1 C2 C3 167.0(2) . . . . ? C11 N1 C2 C7 -158.3(2) . . . . ? C1 N1 C2 C7 -14.1(2) . . . . ? N1 C2 C3 C4 178.4(2) . . . . ? C7 C2 C3 C4 -0.3(3) . . . . ? C2 C3 C4 C5 -0.6(4) . . . . ? C3 C4 C5 C6 0.6(4) . . . . ? C4 C5 C6 C7 0.3(4) . . . . ? C5 C6 C7 N2 179.6(2) . . . . ? C5 C6 C7 C2 -1.3(4) . . . . ? C18 N2 C7 C6 -23.5(4) . . . . ? C1 N2 C7 C6 -169.2(3) . . . . ? C18 N2 C7 C2 157.3(2) . . . . ? C1 N2 C7 C2 11.6(2) . . . . ? C3 C2 C7 C6 1.3(4) . . . . ? N1 C2 C7 C6 -177.7(2) . . . . ? C3 C2 C7 N2 -179.4(2) . . . . ? N1 C2 C7 N2 1.6(2) . . . . ? C9 N3 C8 C1 -2.5(3) . . . . ? C25 N3 C8 C1 178.7(2) . . . . ? C9 N3 C8 S1 177.0(2) . . . . ? C25 N3 C8 S1 -1.8(4) . . . . ? N2 C1 C8 N3 121.3(2) . . . . ? N1 C1 C8 N3 -123.9(2) . . . . ? C10 C1 C8 N3 0.8(2) . . . . ? N2 C1 C8 S1 -58.2(3) . . . . ? N1 C1 C8 S1 56.6(3) . . . . ? C10 C1 C8 S1 -178.74(19) . . . . ? C8 N3 C9 C10 3.5(3) . . . . ? C25 N3 C9 C10 -177.6(2) . . . . ? N3 C9 C10 C31 -178.6(2) . . . . ? N3 C9 C10 C1 -2.9(3) . . . . ? N2 C1 C10 C9 -119.0(2) . . . . ? N1 C1 C10 C9 123.4(2) . . . . ? C8 C1 C10 C9 1.3(3) . . . . ? N2 C1 C10 C31 56.3(3) . . . . ? N1 C1 C10 C31 -61.3(3) . . . . ? C8 C1 C10 C31 176.6(2) . . . . ? C2 N1 C11 C12 -77.7(3) . . . . ? C1 N1 C11 C12 142.1(2) . . . . ? N1 C11 C12 C17 -27.2(3) . . . . ? N1 C11 C12 C13 156.4(2) . . . . ? C17 C12 C13 C14 -1.9(4) . . . . ? C11 C12 C13 C14 174.6(3) . . . . ? C12 C13 C14 C15 1.1(5) . . . . ? C13 C14 C15 C16 0.2(5) . . . . ? C14 C15 C16 C17 -0.7(5) . . . . ? C13 C12 C17 C16 1.4(4) . . . . ? C11 C12 C17 C16 -175.0(3) . . . . ? C15 C16 C17 C12 -0.2(5) . . . . ? C7 N2 C18 C19 82.6(3) . . . . ? C1 N2 C18 C19 -135.2(2) . . . . ? N2 C18 C19 C20 7.8(3) . . . . ? N2 C18 C19 C24 -173.9(2) . . . . ? C24 C19 C20 C21 0.4(4) . . . . ? C18 C19 C20 C21 178.7(2) . . . . ? C19 C20 C21 C22 -1.3(4) . . . . ? C20 C21 C22 C23 0.9(5) . . . . ? C21 C22 C23 C24 0.3(5) . . . . ? C22 C23 C24 C19 -1.1(4) . . . . ? C20 C19 C24 C23 0.7(4) . . . . ? C18 C19 C24 C23 -177.6(2) . . . . ? C8 N3 C25 C30 110.3(3) . . . . ? C9 N3 C25 C30 -68.4(3) . . . . ? C8 N3 C25 C26 -73.0(4) . . . . ? C9 N3 C25 C26 108.3(3) . . . . ? C30 C25 C26 C27 1.5(4) . . . . ? N3 C25 C26 C27 -175.1(3) . . . . ? C25 C26 C27 C28 0.5(5) . . . . ? C26 C27 C28 C29 -2.0(6) . . . . ? C27 C28 C29 C30 1.4(6) . . . . ? C26 C25 C30 C29 -2.1(5) . . . . ? N3 C25 C30 C29 174.6(3) . . . . ? C28 C29 C30 C25 0.6(5) . . . . ? C32 O2 C31 O1 -6.9(4) . . . . ? C32 O2 C31 C10 171.8(2) . . . . ? C9 C10 C31 O1 16.2(4) . . . . ? C1 C10 C31 O1 -158.5(3) . . . . ? C9 C10 C31 O2 -162.4(2) . . . . ? C1 C10 C31 O2 22.8(4) . . . . ? C31 O2 C32 C33 -82.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.210 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.040