#Supplementary Material (ESI) for Journal of Materials Chemistry #This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'Fu Ying Hao' _publ_contact_author_email YXF301129@163.COM _publ_section_title ; Design, Crystal Structures and Enhanced Frequency-upconverted Lasing Efficiencies of a New series of Dyes from Hybrid of Inorganic Polymers and Organic Chromophores ; loop_ _publ_author_name 'Fu Ying Hao' 'Min-Hua Jiang' 'Baokang Jin' 'Lin Li' 'Xutang Tao' ; Yu-Peng Tian ; 'Jie-Ying Wu' 'Jia-Xiang Yang' 'Sheng-Yi Zhang' 'GuangYong Zhou' ; Hongping Zhou ; data_4-I _database_code_depnum_ccdc_archive 'CCDC 245757' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H35 I N2 O2' _chemical_formula_weight 486.42 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' I I -0.4742 1.8119 '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 8.5069(10) _cell_length_b 9.9764(14) _cell_length_c 15.946(2) _cell_angle_alpha 87.271(9) _cell_angle_beta 79.544(9) _cell_angle_gamma 65.359(10) _cell_volume 1209.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 30 _cell_measurement_theta_min 5.41 _cell_measurement_theta_max 12.52 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 1.341 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6735 _exptl_absorpt_correction_T_max 0.7752 _exptl_absorpt_process_details sadads _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 'Bruker P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% multiscan _diffrn_reflns_number 5191 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4250 _reflns_number_gt 3194 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0754P)^2^+0.6933P] 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 0.0029(2) _refine_ls_number_reflns 4250 _refine_ls_number_parameters 256 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1258 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 0.932 _refine_ls_restrained_S_all 0.962 _refine_ls_shift/su_max 0.002 _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 I1 I 0.53036(5) 0.60538(3) 0.33792(3) 0.08237(18) Uani 1 1 d . . . N1 N -0.2014(5) 0.1009(4) 0.4301(2) 0.0568(8) Uani 1 1 d . . . N2 N 1.0163(7) 0.1154(6) 0.1161(4) 0.117(2) Uani 1 1 d . . . C1 C -0.3671(6) 0.0877(6) 0.4656(3) 0.0749(14) Uani 1 1 d . . . H1A H -0.4562 0.1829 0.4859 0.112 Uiso 1 1 calc R . . H1B H -0.3488 0.0211 0.5120 0.112 Uiso 1 1 calc R . . H1C H -0.4040 0.0505 0.4220 0.112 Uiso 1 1 calc R . . C2 C -0.1923(6) 0.2304(5) 0.4308(3) 0.0680(12) Uani 1 1 d . . . H2A H -0.2921 0.3134 0.4531 0.082 Uiso 1 1 calc R . . C3 C -0.0395(6) 0.2447(5) 0.3997(3) 0.0677(12) Uani 1 1 d . . . H3A H -0.0367 0.3366 0.4016 0.081 Uiso 1 1 calc R . . C4 C 0.1117(5) 0.1231(5) 0.3652(3) 0.0564(10) Uani 1 1 d . . . C5 C 0.0965(6) -0.0115(5) 0.3648(3) 0.0598(11) Uani 1 1 d . . . H5A H 0.1937 -0.0961 0.3421 0.072 Uiso 1 1 calc R . . C6 C -0.0575(6) -0.0202(5) 0.3970(3) 0.0601(11) Uani 1 1 d . . . H6A H -0.0644 -0.1107 0.3964 0.072 Uiso 1 1 calc R . . C7 C 0.2679(6) 0.1446(5) 0.3299(3) 0.0605(11) Uani 1 1 d . . . H7A H 0.2623 0.2392 0.3344 0.073 Uiso 1 1 calc R . . C8 C 0.4204(6) 0.0397(5) 0.2913(3) 0.0609(11) Uani 1 1 d . . . H8A H 0.4281 -0.0560 0.2905 0.073 Uiso 1 1 calc R . . C9 C 0.5758(6) 0.0619(5) 0.2502(3) 0.0623(11) Uani 1 1 d . . . C10 C 0.5815(6) 0.1999(5) 0.2440(3) 0.0678(12) Uani 1 1 d . . . H10A H 0.4846 0.2821 0.2697 0.081 Uiso 1 1 calc R . . C11 C 0.7259(7) 0.2176(6) 0.2010(3) 0.0752(13) Uani 1 1 d . . . H11A H 0.7242 0.3115 0.1975 0.090 Uiso 1 1 calc R . . C12 C 0.8765(7) 0.0972(6) 0.1621(3) 0.0785(14) Uani 1 1 d . . . C13 C 0.8699(8) -0.0407(7) 0.1723(4) 0.0886(16) Uani 1 1 d . . . H13A H 0.9683 -0.1243 0.1495 0.106 Uiso 1 1 calc R . . C14 C 0.7255(7) -0.0568(6) 0.2140(3) 0.0737(13) Uani 1 1 d . . . H14A H 0.7275 -0.1508 0.2184 0.088 Uiso 1 1 calc R . . C15 C 1.0051(11) 0.2662(10) 0.0908(5) 0.122(3) Uani 1 1 d . . . H15A H 1.0808 0.2591 0.0363 0.146 Uiso 1 1 calc R . . H15B H 0.8854 0.3308 0.0850 0.146 Uiso 1 1 calc R . . C16 C 1.0592(10) 0.3267(10) 0.1557(5) 0.124(3) Uani 1 1 d . . . H16A H 1.1803 0.2635 0.1596 0.149 Uiso 1 1 calc R . . H16B H 0.9869 0.3286 0.2106 0.149 Uiso 1 1 calc R . . C17 C 1.0419(12) 0.4862(9) 0.1346(6) 0.132(3) Uani 1 1 d . . . H17A H 1.1044 0.4862 0.0773 0.158 Uiso 1 1 calc R . . H17B H 0.9190 0.5517 0.1365 0.158 Uiso 1 1 calc R . . C18 C 1.1131(17) 0.5404(12) 0.1951(9) 0.189(5) Uani 1 1 d . . . H18A H 1.1009 0.6385 0.1809 0.283 Uiso 1 1 calc R . . H18B H 1.2351 0.4766 0.1926 0.283 Uiso 1 1 calc R . . H18C H 1.0500 0.5419 0.2517 0.283 Uiso 1 1 calc R . . C19 C 1.1763(15) -0.0199(14) 0.0551(6) 0.170(4) Uani 1 1 d D . . H19A H 1.1366 -0.0901 0.0368 0.203 Uiso 1 1 calc R . . H19B H 1.2296 0.0166 0.0057 0.203 Uiso 1 1 calc R . . C20 C 1.2856(16) -0.0777(15) 0.1119(7) 0.184(5) Uani 1 1 d D . . H20A H 1.2400 -0.1265 0.1576 0.221 Uiso 1 1 calc R . . H20B H 1.3156 -0.0053 0.1353 0.221 Uiso 1 1 calc R . . C21 C 1.454(2) -0.1981(16) 0.0420(11) 0.239(8) Uani 1 1 d D . . H21A H 1.4248 -0.1808 -0.0148 0.287 Uiso 1 1 calc R . . H21B H 1.5576 -0.1800 0.0414 0.287 Uiso 1 1 calc R . . C22 C 1.491(3) -0.3376(19) 0.0603(13) 0.335(15) Uani 1 1 d D . . H22A H 1.5889 -0.4008 0.0196 0.503 Uiso 1 1 calc R . . H22B H 1.3904 -0.3576 0.0581 0.503 Uiso 1 1 calc R . . H22C H 1.5190 -0.3554 0.1165 0.503 Uiso 1 1 calc R . . O1W O 0.8304(7) 0.6843(6) 0.4373(4) 0.1086(14) Uani 1 1 d D . . O2W O 0.8083(7) 0.5167(5) 0.5815(4) 0.1152(15) Uani 1 1 d D . . H1BW H 0.771(6) 0.677(6) 0.404(2) 0.080 Uiso 1 1 d D . . H1AW H 0.820(7) 0.642(6) 0.4820(18) 0.080 Uiso 1 1 d D . . H2AW H 0.720(3) 0.501(5) 0.589(4) 0.080 Uiso 1 1 d D . . H2BW H 0.897(3) 0.439(3) 0.572(4) 0.080 Uiso 1 1 d 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 I1 0.0689(2) 0.0564(2) 0.1134(3) -0.00037(17) -0.00912(19) -0.02036(16) N1 0.0475(19) 0.067(2) 0.057(2) 0.0043(17) -0.0110(16) -0.0245(17) N2 0.078(3) 0.095(4) 0.160(5) -0.011(4) 0.042(3) -0.042(3) C1 0.053(3) 0.098(4) 0.080(3) 0.008(3) -0.008(2) -0.041(3) C2 0.053(3) 0.059(3) 0.082(3) 0.001(2) -0.006(2) -0.015(2) C3 0.060(3) 0.050(2) 0.090(3) 0.003(2) -0.005(2) -0.023(2) C4 0.052(2) 0.061(2) 0.059(2) 0.0073(19) -0.013(2) -0.025(2) C5 0.052(2) 0.054(2) 0.069(3) -0.003(2) -0.010(2) -0.0170(19) C6 0.059(3) 0.058(2) 0.069(3) 0.002(2) -0.013(2) -0.029(2) C7 0.058(3) 0.053(2) 0.074(3) 0.005(2) -0.016(2) -0.025(2) C8 0.056(3) 0.068(3) 0.064(3) 0.005(2) -0.013(2) -0.029(2) C9 0.058(3) 0.070(3) 0.062(3) 0.004(2) -0.011(2) -0.030(2) C10 0.052(3) 0.065(3) 0.079(3) -0.005(2) 0.000(2) -0.021(2) C11 0.062(3) 0.065(3) 0.094(4) 0.003(3) 0.001(3) -0.029(2) C12 0.062(3) 0.087(4) 0.085(3) -0.004(3) 0.003(3) -0.035(3) C13 0.073(4) 0.077(4) 0.102(4) -0.010(3) 0.011(3) -0.027(3) C14 0.068(3) 0.063(3) 0.084(3) -0.001(2) 0.004(3) -0.028(2) C15 0.093(5) 0.162(8) 0.113(5) 0.016(5) 0.000(4) -0.065(5) C16 0.088(5) 0.148(7) 0.128(6) 0.043(5) -0.021(4) -0.045(5) C17 0.124(6) 0.099(5) 0.174(8) 0.050(5) -0.046(6) -0.045(5) C18 0.192(12) 0.121(8) 0.265(14) 0.049(8) -0.087(11) -0.063(8) C19 0.201(11) 0.243(13) 0.132(7) 0.042(8) -0.039(8) -0.157(11) C20 0.231(13) 0.276(15) 0.128(8) 0.037(9) -0.058(9) -0.178(13) C21 0.168(12) 0.190(14) 0.264(17) -0.066(14) 0.021(11) 0.001(11) C22 0.35(3) 0.211(18) 0.29(2) -0.044(17) 0.11(2) -0.028(19) O1W 0.102(3) 0.101(3) 0.139(4) 0.005(3) -0.028(3) -0.055(3) O2W 0.087(3) 0.097(3) 0.161(4) -0.015(3) 0.004(3) -0.046(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 N1 C2 1.327(6) . ? N1 C6 1.353(6) . ? N1 C1 1.477(6) . ? N2 C12 1.355(7) . ? N2 C15 1.507(10) . ? N2 C19 1.653(13) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.367(7) . ? C2 H2A 0.9300 . ? C3 C4 1.391(6) . ? C3 H3A 0.9300 . ? C4 C5 1.402(6) . ? C4 C7 1.444(6) . ? C5 C6 1.354(6) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.340(6) . ? C7 H7A 0.9300 . ? C8 C9 1.464(6) . ? C8 H8A 0.9300 . ? C9 C14 1.378(7) . ? C9 C10 1.396(7) . ? C10 C11 1.369(7) . ? C10 H10A 0.9300 . ? C11 C12 1.403(7) . ? C11 H11A 0.9300 . ? C12 C13 1.401(8) . ? C13 C14 1.355(7) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.452(11) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.562(11) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.458(13) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.351(11) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.688(13) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.324(15) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? O1W H1BW 0.818(10) . ? O1W H1AW 0.819(10) . ? O2W H2AW 0.821(10) . ? O2W H2BW 0.822(10) . ? 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 C6 119.7(4) . . ? C2 N1 C1 120.6(4) . . ? C6 N1 C1 119.7(4) . . ? C12 N2 C15 121.4(5) . . ? C12 N2 C19 121.4(6) . . ? C15 N2 C19 113.4(5) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 121.6(4) . . ? N1 C2 H2A 119.2 . . ? C3 C2 H2A 119.2 . . ? C2 C3 C4 120.7(4) . . ? C2 C3 H3A 119.7 . . ? C4 C3 H3A 119.7 . . ? C3 C4 C5 116.1(4) . . ? C3 C4 C7 118.7(4) . . ? C5 C4 C7 125.1(4) . . ? C6 C5 C4 121.0(4) . . ? C6 C5 H5A 119.5 . . ? C4 C5 H5A 119.5 . . ? N1 C6 C5 121.0(4) . . ? N1 C6 H6A 119.5 . . ? C5 C6 H6A 119.5 . . ? C8 C7 C4 125.5(4) . . ? C8 C7 H7A 117.3 . . ? C4 C7 H7A 117.3 . . ? C7 C8 C9 126.0(5) . . ? C7 C8 H8A 117.0 . . ? C9 C8 H8A 117.0 . . ? C14 C9 C10 116.7(4) . . ? C14 C9 C8 119.9(4) . . ? C10 C9 C8 123.4(4) . . ? C11 C10 C9 121.7(4) . . ? C11 C10 H10A 119.1 . . ? C9 C10 H10A 119.1 . . ? C10 C11 C12 121.5(5) . . ? C10 C11 H11A 119.3 . . ? C12 C11 H11A 119.3 . . ? N2 C12 C13 122.9(5) . . ? N2 C12 C11 121.5(5) . . ? C13 C12 C11 115.6(5) . . ? C14 C13 C12 122.5(5) . . ? C14 C13 H13A 118.8 . . ? C12 C13 H13A 118.8 . . ? C13 C14 C9 121.9(5) . . ? C13 C14 H14A 119.0 . . ? C9 C14 H14A 119.0 . . ? C16 C15 N2 109.3(7) . . ? C16 C15 H15A 109.8 . . ? N2 C15 H15A 109.8 . . ? C16 C15 H15B 109.8 . . ? N2 C15 H15B 109.8 . . ? H15A C15 H15B 108.3 . . ? C15 C16 C17 111.3(7) . . ? C15 C16 H16A 109.4 . . ? C17 C16 H16A 109.4 . . ? C15 C16 H16B 109.4 . . ? C17 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C18 C17 C16 111.0(8) . . ? C18 C17 H17A 109.4 . . ? C16 C17 H17A 109.4 . . ? C18 C17 H17B 109.4 . . ? C16 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 N2 98.8(9) . . ? C20 C19 H19A 112.0 . . ? N2 C19 H19A 112.0 . . ? C20 C19 H19B 112.0 . . ? N2 C19 H19B 112.0 . . ? H19A C19 H19B 109.7 . . ? C19 C20 C21 95.8(10) . . ? C19 C20 H20A 112.6 . . ? C21 C20 H20A 112.6 . . ? C19 C20 H20B 112.6 . . ? C21 C20 H20B 112.6 . . ? H20A C20 H20B 110.1 . . ? C22 C21 C20 113.0(15) . . ? C22 C21 H21A 109.0 . . ? C20 C21 H21A 109.0 . . ? C22 C21 H21B 109.0 . . ? C20 C21 H21B 109.0 . . ? H21A C21 H21B 107.8 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? H1BW O1W H1AW 113(3) . . ? H2AW O2W H2BW 110(3) . . ? 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 C6 N1 C2 C3 -0.7(7) . . . . ? C1 N1 C2 C3 178.8(5) . . . . ? N1 C2 C3 C4 0.7(8) . . . . ? C2 C3 C4 C5 -0.1(7) . . . . ? C2 C3 C4 C7 177.5(4) . . . . ? C3 C4 C5 C6 -0.4(7) . . . . ? C7 C4 C5 C6 -177.8(4) . . . . ? C2 N1 C6 C5 0.2(7) . . . . ? C1 N1 C6 C5 -179.3(4) . . . . ? C4 C5 C6 N1 0.4(7) . . . . ? C3 C4 C7 C8 -176.9(5) . . . . ? C5 C4 C7 C8 0.5(7) . . . . ? C4 C7 C8 C9 175.7(4) . . . . ? C7 C8 C9 C14 178.9(5) . . . . ? C7 C8 C9 C10 -2.2(8) . . . . ? C14 C9 C10 C11 2.6(8) . . . . ? C8 C9 C10 C11 -176.3(5) . . . . ? C9 C10 C11 C12 -0.9(8) . . . . ? C15 N2 C12 C13 166.9(7) . . . . ? C19 N2 C12 C13 10.2(11) . . . . ? C15 N2 C12 C11 -11.3(11) . . . . ? C19 N2 C12 C11 -168.0(7) . . . . ? C10 C11 C12 N2 176.7(6) . . . . ? C10 C11 C12 C13 -1.6(8) . . . . ? N2 C12 C13 C14 -175.9(6) . . . . ? C11 C12 C13 C14 2.4(9) . . . . ? C12 C13 C14 C9 -0.7(9) . . . . ? C10 C9 C14 C13 -1.8(8) . . . . ? C8 C9 C14 C13 177.2(5) . . . . ? C12 N2 C15 C16 91.5(9) . . . . ? C19 N2 C15 C16 -110.1(8) . . . . ? N2 C15 C16 C17 -177.4(6) . . . . ? C15 C16 C17 C18 -174.2(9) . . . . ? C12 N2 C19 C20 -92.7(10) . . . . ? C15 N2 C19 C20 108.9(9) . . . . ? N2 C19 C20 C21 -172.9(8) . . . . ? C19 C20 C21 C22 -115(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2W H2AW I1 0.821(10) 2.81(2) 3.587(5) 160(5) 2_666 O2W H2BW O1W 0.822(10) 2.10(2) 2.854(7) 152(4) 2_766 O1W H1AW O2W 0.819(10) 1.990(16) 2.804(8) 173(6) . O1W H1BW I1 0.818(10) 2.81(2) 3.592(5) 161(4) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.555 _refine_diff_density_min -0.553 _refine_diff_density_rms 0.069 # Attachment 'Cifs.cif' data_3-i _database_code_depnum_ccdc_archive 'CCDC 246081' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H29 I N2 O' _chemical_formula_weight 440.35 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.0256(12) _cell_length_b 8.8242(10) _cell_length_c 17.4227(18) _cell_angle_alpha 90.00 _cell_angle_beta 115.336(6) _cell_angle_gamma 90.00 _cell_volume 2087.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 32 _cell_measurement_theta_min 5.284 _cell_measurement_theta_max 12.401 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 1.542 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.595 _exptl_absorpt_correction_T_max 0.661 _exptl_absorpt_process_details sadads _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 'Bruker P4' _diffrn_measurement_method \q/2\q _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4723 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 24.98 _reflns_number_total 3689 _reflns_number_gt 2706 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0267P)^2^+0.7331P] 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 restr _refine_ls_extinction_method none _refine_ls_extinction_coef 0.0029(2) _refine_ls_number_reflns 3689 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0577 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0784 _refine_ls_wR_factor_gt 0.0701 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 I1 I 0.14284(2) 0.13354(3) 0.262096(16) 0.06453(11) Uani 1 1 d . . . N1 N 0.0844(2) -0.2707(3) -0.06450(17) 0.0480(7) Uani 1 1 d . . . N2 N 0.3671(2) 0.8475(3) 0.15170(17) 0.0485(7) Uani 1 1 d . . . C1 C 0.0384(3) -0.4214(4) -0.0901(3) 0.0643(11) Uani 1 1 d . . . H1A H 0.0430 -0.4534 -0.1409 0.096 Uiso 1 1 calc R . . H1B H -0.0297 -0.4158 -0.1005 0.096 Uiso 1 1 calc R . . H1C H 0.0718 -0.4931 -0.0455 0.096 Uiso 1 1 calc R . . C2 C 0.1221(3) -0.1998(5) -0.1116(2) 0.0623(10) Uani 1 1 d . . . H2A H 0.1209 -0.2477 -0.1596 0.075 Uiso 1 1 calc R . . C3 C 0.1620(3) -0.0597(5) -0.0910(2) 0.0634(11) Uani 1 1 d . . . H3A H 0.1883 -0.0137 -0.1247 0.076 Uiso 1 1 calc R . . C4 C 0.1644(3) 0.0161(4) -0.0210(2) 0.0519(9) Uani 1 1 d . . . C5 C 0.1250(3) -0.0600(4) 0.0272(2) 0.0531(9) Uani 1 1 d . . . H5A H 0.1255 -0.0140 0.0754 0.064 Uiso 1 1 calc R . . C6 C 0.0855(3) -0.2023(4) 0.0045(2) 0.0503(9) Uani 1 1 d . . . H6A H 0.0593 -0.2516 0.0373 0.060 Uiso 1 1 calc R . . C7 C 0.2061(3) 0.1691(5) -0.0026(2) 0.0597(10) Uani 1 1 d . . . H7A H 0.2294 0.2105 -0.0396 0.072 Uiso 1 1 calc R . . C8 C 0.2132(3) 0.2525(5) 0.0623(2) 0.0569(10) Uani 1 1 d . . . H8A H 0.1909 0.2091 0.0995 0.068 Uiso 1 1 calc R . . C9 C 0.2525(2) 0.4060(4) 0.0822(2) 0.0499(9) Uani 1 1 d . . . C10 C 0.2962(3) 0.4838(4) 0.0371(2) 0.0559(10) Uani 1 1 d . . . H10A H 0.2995 0.4373 -0.0094 0.067 Uiso 1 1 calc R . . C11 C 0.3345(2) 0.6276(4) 0.0599(2) 0.0498(8) Uani 1 1 d . . . H11A H 0.3636 0.6750 0.0288 0.060 Uiso 1 1 calc R . . C12 C 0.3306(2) 0.7046(4) 0.1293(2) 0.0440(8) Uani 1 1 d . . . C13 C 0.2831(3) 0.6261(4) 0.1721(2) 0.0522(9) Uani 1 1 d . . . H13A H 0.2759 0.6734 0.2169 0.063 Uiso 1 1 calc R . . C14 C 0.2474(3) 0.4820(5) 0.1494(2) 0.0556(10) Uani 1 1 d . . . H14A H 0.2185 0.4336 0.1804 0.067 Uiso 1 1 calc R . . C15 C 0.4218(4) 0.8974(6) 0.3852(3) 0.0957(16) Uani 1 1 d . . . H15A H 0.4739 0.8605 0.4366 0.144 Uiso 1 1 calc R . . H15B H 0.3609 0.8503 0.3772 0.144 Uiso 1 1 calc R . . H15C H 0.4162 1.0053 0.3889 0.144 Uiso 1 1 calc R . . C16 C 0.4446(3) 0.8599(5) 0.3107(2) 0.0698(11) Uani 1 1 d . . . H16A H 0.4498 0.7508 0.3069 0.084 Uiso 1 1 calc R . . H16B H 0.5076 0.9039 0.3202 0.084 Uiso 1 1 calc R . . C17 C 0.3659(3) 0.9191(5) 0.2271(2) 0.0599(10) Uani 1 1 d . . . H17A H 0.3017 0.9030 0.2266 0.072 Uiso 1 1 calc R . . H17B H 0.3747 1.0275 0.2241 0.072 Uiso 1 1 calc R . . C18 C 0.4303(3) 0.9148(4) 0.1165(2) 0.0534(9) Uani 1 1 d . . . H18A H 0.4340 1.0231 0.1269 0.064 Uiso 1 1 calc R . . H18B H 0.4001 0.8995 0.0555 0.064 Uiso 1 1 calc R . . C19 C 0.5333(3) 0.8513(5) 0.1526(3) 0.0655(11) Uani 1 1 d . . . H19A H 0.5665 0.8776 0.2123 0.079 Uiso 1 1 calc R . . H19B H 0.5296 0.7417 0.1486 0.079 Uiso 1 1 calc R . . C20 C 0.5938(3) 0.9080(6) 0.1084(3) 0.0837(14) Uani 1 1 d . . . H20A H 0.6578 0.8619 0.1335 0.126 Uiso 1 1 calc R . . H20B H 0.6005 1.0161 0.1144 0.126 Uiso 1 1 calc R . . H20C H 0.5616 0.8821 0.0493 0.126 Uiso 1 1 calc R . . O1W O 0.0453(3) 0.7629(5) 0.1710(2) 0.0954(12) Uani 1 1 d . . . H2W H 0.068(3) 0.858(5) 0.193(3) 0.080 Uiso 1 1 d . . . H1W H -0.003(3) 0.741(5) 0.184(3) 0.080 Uiso 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 I1 0.06668(18) 0.0756(2) 0.05998(16) 0.00026(15) 0.03543(13) -0.00114(16) N1 0.0452(17) 0.0472(18) 0.0496(16) -0.0043(14) 0.0186(14) -0.0049(14) N2 0.0479(16) 0.0489(18) 0.0489(15) -0.0036(14) 0.0208(13) -0.0059(15) C1 0.062(2) 0.051(2) 0.077(3) -0.011(2) 0.028(2) -0.008(2) C2 0.065(3) 0.075(3) 0.050(2) -0.013(2) 0.028(2) -0.011(2) C3 0.063(3) 0.075(3) 0.055(2) -0.003(2) 0.028(2) -0.019(2) C4 0.043(2) 0.054(2) 0.051(2) 0.0028(19) 0.0133(17) -0.0042(18) C5 0.054(2) 0.057(2) 0.0435(19) -0.0052(18) 0.0166(18) 0.006(2) C6 0.048(2) 0.055(2) 0.048(2) 0.0034(19) 0.0215(17) 0.0022(19) C7 0.057(2) 0.071(3) 0.054(2) 0.008(2) 0.0264(19) -0.004(2) C8 0.046(2) 0.069(3) 0.050(2) 0.006(2) 0.0166(18) -0.003(2) C9 0.0399(19) 0.053(2) 0.050(2) 0.0028(18) 0.0132(16) -0.0050(17) C10 0.051(2) 0.064(3) 0.0462(19) -0.0084(19) 0.0149(18) 0.000(2) C11 0.0477(19) 0.058(2) 0.0441(17) 0.0010(19) 0.0199(15) -0.0043(19) C12 0.0353(17) 0.049(2) 0.0447(18) 0.0010(17) 0.0143(15) 0.0003(17) C13 0.050(2) 0.062(2) 0.0450(18) -0.0078(19) 0.0208(16) -0.008(2) C14 0.050(2) 0.066(3) 0.049(2) 0.0040(19) 0.0192(18) -0.011(2) C15 0.125(4) 0.104(4) 0.073(3) -0.009(3) 0.058(3) -0.021(3) C16 0.066(3) 0.086(3) 0.053(2) -0.018(2) 0.021(2) -0.014(3) C17 0.068(3) 0.052(2) 0.064(2) -0.0087(19) 0.032(2) -0.002(2) C18 0.054(2) 0.044(2) 0.060(2) 0.0016(18) 0.0231(18) -0.0076(18) C19 0.054(2) 0.075(3) 0.066(2) 0.002(2) 0.024(2) -0.007(2) C20 0.065(3) 0.104(4) 0.092(3) 0.005(3) 0.043(2) -0.001(3) O1W 0.113(3) 0.098(3) 0.100(3) -0.014(2) 0.069(2) -0.020(2) _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 N1 C2 1.336(4) . ? N1 C6 1.339(4) . ? N1 C1 1.478(5) . ? N2 C12 1.364(4) . ? N2 C18 1.458(4) . ? N2 C17 1.465(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.354(6) . ? C2 H2A 0.9300 . ? C3 C4 1.377(5) . ? C3 H3A 0.9300 . ? C4 C5 1.390(5) . ? C4 C7 1.465(5) . ? C5 C6 1.373(5) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.315(5) . ? C7 H7A 0.9300 . ? C8 C9 1.459(5) . ? C8 H8A 0.9300 . ? C9 C14 1.379(5) . ? C9 C10 1.400(5) . ? C10 C11 1.380(5) . ? C10 H10A 0.9300 . ? C11 C12 1.408(5) . ? C11 H11A 0.9300 . ? C12 C13 1.415(5) . ? C13 C14 1.371(5) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.514(6) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.522(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.508(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.506(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? O1W H2W 0.92(4) . ? O1W H1W 0.87(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 C2 N1 C6 119.7(3) . . ? C2 N1 C1 120.2(3) . . ? C6 N1 C1 120.1(3) . . ? C12 N2 C18 120.7(3) . . ? C12 N2 C17 119.8(3) . . ? C18 N2 C17 117.5(3) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 121.3(4) . . ? N1 C2 H2A 119.3 . . ? C3 C2 H2A 119.3 . . ? C2 C3 C4 121.3(4) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C3 C4 C5 116.3(3) . . ? C3 C4 C7 119.3(3) . . ? C5 C4 C7 124.4(3) . . ? C6 C5 C4 120.7(3) . . ? C6 C5 H5A 119.6 . . ? C4 C5 H5A 119.6 . . ? N1 C6 C5 120.6(3) . . ? N1 C6 H6A 119.7 . . ? C5 C6 H6A 119.7 . . ? C8 C7 C4 125.0(4) . . ? C8 C7 H7A 117.5 . . ? C4 C7 H7A 117.5 . . ? C7 C8 C9 126.8(4) . . ? C7 C8 H8A 116.6 . . ? C9 C8 H8A 116.6 . . ? C14 C9 C10 116.6(3) . . ? C14 C9 C8 119.3(3) . . ? C10 C9 C8 124.2(3) . . ? C11 C10 C9 121.8(3) . . ? C11 C10 H10A 119.1 . . ? C9 C10 H10A 119.1 . . ? C10 C11 C12 121.7(3) . . ? C10 C11 H11A 119.2 . . ? C12 C11 H11A 119.2 . . ? N2 C12 C11 122.2(3) . . ? N2 C12 C13 122.2(3) . . ? C11 C12 C13 115.6(3) . . ? C14 C13 C12 121.7(3) . . ? C14 C13 H13A 119.2 . . ? C12 C13 H13A 119.2 . . ? C13 C14 C9 122.6(3) . . ? C13 C14 H14A 118.7 . . ? C9 C14 H14A 118.7 . . ? C16 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C16 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C15 C16 C17 112.1(4) . . ? C15 C16 H16A 109.2 . . ? C17 C16 H16A 109.2 . . ? C15 C16 H16B 109.2 . . ? C17 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? N2 C17 C16 114.0(3) . . ? N2 C17 H17A 108.8 . . ? C16 C17 H17A 108.8 . . ? N2 C17 H17B 108.8 . . ? C16 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? N2 C18 C19 114.2(3) . . ? N2 C18 H18A 108.7 . . ? C19 C18 H18A 108.7 . . ? N2 C18 H18B 108.7 . . ? C19 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? C20 C19 C18 113.6(3) . . ? C20 C19 H19A 108.8 . . ? C18 C19 H19A 108.8 . . ? C20 C19 H19B 108.8 . . ? C18 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? H2W O1W H1W 107(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.385 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.057 data_1-SCN _database_code_depnum_ccdc_archive 'CCDC 246082' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H19 Cd N5 S3' _chemical_formula_weight 525.97 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 14.3163(3) _cell_length_b 10.7538(3) _cell_length_c 28.2371(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4347.23(19) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7307 _cell_measurement_theta_min 1.44 _cell_measurement_theta_max 28.33 _exptl_crystal_description slab _exptl_crystal_colour dark-red _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2112 _exptl_absorpt_coefficient_mu 1.307 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6504 _exptl_absorpt_correction_T_max 0.8381 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 29135 _diffrn_reflns_av_R_equivalents 0.1237 _diffrn_reflns_av_sigmaI/netI 0.0839 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 28.30 _reflns_number_total 5361 _reflns_number_gt 3428 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990) ; _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^)+(0.0560P)^2^+0.0000P] 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 restr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0029(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5361 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0785 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1190 _refine_ls_wR_factor_gt 0.0992 _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_restrained_S_all 0.937 _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 Cd1 Cd 0.219299(18) 0.62746(2) -0.312344(10) 0.03488(12) Uani 1 1 d . . . S1 S 0.43711(7) 0.98634(8) -0.30983(4) 0.0428(3) Uani 1 1 d . . . S2 S 0.12571(7) 0.76025(9) -0.38021(4) 0.0418(3) Uani 1 1 d . . . S3 S 0.14015(7) 0.75918(8) -0.23841(4) 0.0420(3) Uani 1 1 d . . . N1 N 0.1048(3) 0.2744(4) -0.48728(13) 0.0591(10) Uani 1 1 d . . . N2 N 0.1110(2) 1.1487(3) -0.67022(13) 0.0423(8) Uani 1 1 d . . . N3 N 0.3449(2) 0.7582(3) -0.31354(12) 0.0417(8) Uani 1 1 d . . . N4 N 0.2106(3) 0.9966(3) -0.25555(14) 0.0536(10) Uani 1 1 d . . . N5 N 0.2095(2) 0.9926(3) -0.36693(13) 0.0472(9) Uani 1 1 d . . . C1 C 0.1337(4) 0.2568(5) -0.43792(16) 0.0699(15) Uani 1 1 d . . . H1A H 0.1221 0.1723 -0.4286 0.105 Uiso 1 1 calc R . . H1B H 0.0987 0.3119 -0.4179 0.105 Uiso 1 1 calc R . . H1C H 0.1991 0.2747 -0.4349 0.105 Uiso 1 1 calc R . . C2 C 0.0550(4) 0.1701(4) -0.50938(19) 0.0727(15) Uani 1 1 d . . . H2A H 0.0564 0.0996 -0.4886 0.109 Uiso 1 1 calc R . . H2B H 0.0848 0.1490 -0.5388 0.109 Uiso 1 1 calc R . . H2C H -0.0086 0.1937 -0.5153 0.109 Uiso 1 1 calc R . . C3 C 0.1143(3) 0.3871(4) -0.50878(14) 0.0441(10) Uani 1 1 d . . . C4 C 0.0755(3) 0.4117(4) -0.55360(15) 0.0500(10) Uani 1 1 d . . . H4A H 0.0438 0.3485 -0.5693 0.060 Uiso 1 1 calc R . . C5 C 0.0829(3) 0.5244(4) -0.57443(15) 0.0507(11) Uani 1 1 d . . . H5A H 0.0559 0.5372 -0.6040 0.061 Uiso 1 1 calc R . . C6 C 0.1303(3) 0.6217(4) -0.55243(15) 0.0472(10) Uani 1 1 d . . . C7 C 0.1699(3) 0.5955(4) -0.50885(16) 0.0559(12) Uani 1 1 d . . . H7A H 0.2032 0.6582 -0.4937 0.067 Uiso 1 1 calc R . . C8 C 0.1631(3) 0.4841(4) -0.48708(16) 0.0576(12) Uani 1 1 d . . . H8A H 0.1908 0.4720 -0.4577 0.069 Uiso 1 1 calc R . . C9 C 0.1382(3) 0.7463(4) -0.57316(16) 0.0507(11) Uani 1 1 d . . . H9A H 0.1773 0.8018 -0.5575 0.061 Uiso 1 1 calc R . . C10 C 0.0960(3) 0.7893(4) -0.61188(16) 0.0488(10) Uani 1 1 d . . . H10A H 0.0580 0.7336 -0.6282 0.059 Uiso 1 1 calc R . . C11 C 0.1030(3) 0.9143(4) -0.63134(14) 0.0433(10) Uani 1 1 d . . . C12 C 0.0388(3) 0.9547(4) -0.66458(15) 0.0453(10) Uani 1 1 d . . . H12A H -0.0085 0.9013 -0.6744 0.054 Uiso 1 1 calc R . . C13 C 0.0434(3) 1.0688(4) -0.68283(14) 0.0456(10) Uani 1 1 d . . . H13A H -0.0012 1.0937 -0.7048 0.055 Uiso 1 1 calc R . . C14 C 0.1768(3) 1.1105(4) -0.63903(18) 0.0565(12) Uani 1 1 d . . . H14A H 0.2250 1.1644 -0.6310 0.068 Uiso 1 1 calc R . . C15 C 0.1742(3) 0.9968(4) -0.61931(17) 0.0565(12) Uani 1 1 d . . . H15A H 0.2199 0.9733 -0.5977 0.068 Uiso 1 1 calc R . . C16 C 0.1127(4) 1.2773(4) -0.68963(16) 0.0603(13) Uani 1 1 d . . . H16A H 0.1654 1.3213 -0.6769 0.090 Uiso 1 1 calc R . . H16B H 0.0562 1.3197 -0.6810 0.090 Uiso 1 1 calc R . . H16C H 0.1176 1.2740 -0.7235 0.090 Uiso 1 1 calc R . . C17 C 0.3828(3) 0.8531(3) -0.31208(13) 0.0321(8) Uani 1 1 d . . . C18 C 0.1753(3) 0.8983(3) -0.37192(13) 0.0330(8) Uani 1 1 d . . . C19 C 0.1818(3) 0.8998(3) -0.24906(13) 0.0332(8) 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 Cd1 0.03670(18) 0.02222(15) 0.0457(2) -0.00059(11) -0.00228(13) -0.00006(11) S1 0.0343(5) 0.0278(4) 0.0663(7) -0.0006(5) 0.0024(5) -0.0028(4) S2 0.0447(6) 0.0338(5) 0.0469(6) -0.0017(4) -0.0106(5) -0.0041(4) S3 0.0503(6) 0.0294(5) 0.0464(6) 0.0022(4) 0.0114(5) -0.0032(4) N1 0.061(2) 0.071(3) 0.045(2) 0.009(2) -0.0115(19) -0.004(2) N2 0.0379(19) 0.047(2) 0.0425(19) -0.0025(15) 0.0086(16) 0.0043(15) N3 0.0381(18) 0.0297(16) 0.057(2) 0.0000(15) 0.0018(16) -0.0004(14) N4 0.068(3) 0.0241(16) 0.069(3) -0.0008(16) 0.021(2) -0.0050(16) N5 0.059(2) 0.0256(16) 0.057(2) -0.0021(15) -0.0101(18) 0.0002(15) C1 0.063(3) 0.099(4) 0.048(3) 0.016(3) -0.008(2) 0.007(3) C2 0.087(4) 0.065(3) 0.065(3) 0.000(3) -0.004(3) -0.010(3) C3 0.039(2) 0.058(3) 0.036(2) 0.005(2) -0.0039(18) 0.0029(19) C4 0.051(3) 0.060(3) 0.039(2) -0.004(2) -0.012(2) -0.002(2) C5 0.051(3) 0.065(3) 0.037(2) -0.001(2) -0.011(2) 0.008(2) C6 0.045(2) 0.055(3) 0.041(2) -0.003(2) 0.0021(19) 0.004(2) C7 0.054(3) 0.068(3) 0.046(3) -0.005(2) -0.010(2) -0.007(2) C8 0.067(3) 0.065(3) 0.040(3) 0.003(2) -0.016(2) -0.004(2) C9 0.038(2) 0.065(3) 0.049(3) -0.012(2) 0.0027(19) 0.001(2) C10 0.036(2) 0.064(3) 0.047(3) -0.009(2) 0.0014(19) 0.001(2) C11 0.039(2) 0.049(2) 0.042(2) -0.0092(19) 0.0100(19) 0.0012(18) C12 0.035(2) 0.050(2) 0.051(3) -0.013(2) -0.0041(19) 0.0013(18) C13 0.037(2) 0.054(3) 0.046(3) -0.012(2) -0.0049(19) 0.0066(19) C14 0.045(2) 0.063(3) 0.062(3) -0.002(2) -0.008(2) -0.011(2) C15 0.047(3) 0.057(3) 0.065(3) 0.006(2) -0.015(2) -0.004(2) C16 0.061(3) 0.057(3) 0.063(3) 0.008(2) 0.015(2) 0.006(2) C17 0.0290(18) 0.0297(17) 0.038(2) 0.0002(15) 0.0027(16) 0.0066(14) C18 0.0352(19) 0.0345(19) 0.0293(19) 0.0007(15) -0.0006(16) 0.0054(16) C19 0.0346(19) 0.0349(19) 0.0301(19) -0.0009(16) 0.0055(16) 0.0033(15) _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 Cd1 N3 2.283(3) . ? Cd1 N5 2.349(3) 7_655 ? Cd1 N4 2.358(3) 7_655 ? Cd1 S1 2.7060(10) 7_655 ? Cd1 S2 2.7398(10) . ? Cd1 S3 2.7656(10) . ? S1 C17 1.631(4) . ? S1 Cd1 2.7060(10) 7_665 ? S2 C18 1.662(4) . ? S3 C19 1.653(4) . ? N1 C3 1.363(5) . ? N1 C1 1.466(5) . ? N1 C2 1.468(6) . ? N2 C13 1.341(5) . ? N2 C14 1.353(6) . ? N2 C16 1.488(5) . ? N3 C17 1.157(4) . ? N4 C19 1.135(4) . ? N4 Cd1 2.358(3) 7_665 ? N5 C18 1.136(4) . ? N5 Cd1 2.349(3) 7_665 ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C8 1.397(6) . ? C3 C4 1.407(5) . ? C4 C5 1.351(6) . ? C4 H4A 0.9300 . ? C5 C6 1.394(6) . ? C5 H5A 0.9300 . ? C6 C7 1.384(6) . ? C6 C9 1.467(6) . ? C7 C8 1.350(6) . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? C9 C10 1.332(6) . ? C9 H9A 0.9300 . ? C10 C11 1.456(6) . ? C10 H10A 0.9300 . ? C11 C12 1.384(6) . ? C11 C15 1.394(6) . ? C12 C13 1.333(5) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 C15 1.344(6) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 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 N3 Cd1 N5 91.64(11) . 7_655 ? N3 Cd1 N4 92.43(12) . 7_655 ? N5 Cd1 N4 83.87(14) 7_655 7_655 ? N3 Cd1 S1 176.05(8) . 7_655 ? N5 Cd1 S1 91.73(8) 7_655 7_655 ? N4 Cd1 S1 89.98(9) 7_655 7_655 ? N3 Cd1 S2 93.09(8) . . ? N5 Cd1 S2 94.31(9) 7_655 . ? N4 Cd1 S2 174.24(8) 7_655 . ? S1 Cd1 S2 84.61(3) 7_655 . ? N3 Cd1 S3 91.05(8) . . ? N5 Cd1 S3 171.61(9) 7_655 . ? N4 Cd1 S3 88.09(10) 7_655 . ? S1 Cd1 S3 85.89(3) 7_655 . ? S2 Cd1 S3 93.48(3) . . ? C17 S1 Cd1 95.56(13) . 7_665 ? C18 S2 Cd1 99.09(13) . . ? C19 S3 Cd1 100.58(13) . . ? C3 N1 C1 120.7(4) . . ? C3 N1 C2 122.6(4) . . ? C1 N1 C2 116.3(4) . . ? C13 N2 C14 118.7(4) . . ? C13 N2 C16 120.6(4) . . ? C14 N2 C16 120.7(4) . . ? C17 N3 Cd1 155.8(3) . . ? C19 N4 Cd1 144.3(3) . 7_665 ? C18 N5 Cd1 145.1(3) . 7_665 ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 C8 121.2(4) . . ? N1 C3 C4 121.9(4) . . ? C8 C3 C4 116.9(4) . . ? C5 C4 C3 121.9(4) . . ? C5 C4 H4A 119.1 . . ? C3 C4 H4A 119.1 . . ? C4 C5 C6 121.2(4) . . ? C4 C5 H5A 119.4 . . ? C6 C5 H5A 119.4 . . ? C7 C6 C5 116.3(4) . . ? C7 C6 C9 120.6(4) . . ? C5 C6 C9 123.1(4) . . ? C8 C7 C6 123.8(4) . . ? C8 C7 H7A 118.1 . . ? C6 C7 H7A 118.1 . . ? C7 C8 C3 119.9(4) . . ? C7 C8 H8A 120.0 . . ? C3 C8 H8A 120.0 . . ? C10 C9 C6 127.5(4) . . ? C10 C9 H9A 116.2 . . ? C6 C9 H9A 116.2 . . ? C9 C10 C11 126.8(4) . . ? C9 C10 H10A 116.6 . . ? C11 C10 H10A 116.6 . . ? C12 C11 C15 116.8(4) . . ? C12 C11 C10 120.0(4) . . ? C15 C11 C10 123.2(4) . . ? C13 C12 C11 121.2(4) . . ? C13 C12 H12A 119.4 . . ? C11 C12 H12A 119.4 . . ? C12 C13 N2 121.5(4) . . ? C12 C13 H13A 119.3 . . ? N2 C13 H13A 119.3 . . ? C15 C14 N2 121.8(4) . . ? C15 C14 H14A 119.1 . . ? N2 C14 H14A 119.1 . . ? C14 C15 C11 119.9(4) . . ? C14 C15 H15A 120.1 . . ? C11 C15 H15A 120.1 . . ? N2 C16 H16A 109.5 . . ? N2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N3 C17 S1 179.4(4) . . ? N5 C18 S2 179.0(4) . . ? N4 C19 S3 178.8(4) . . ? 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 N3 Cd1 S2 C18 -25.08(16) . . . . ? N5 Cd1 S2 C18 -116.96(16) 7_655 . . . ? N4 Cd1 S2 C18 171.8(10) 7_655 . . . ? S1 Cd1 S2 C18 151.70(14) 7_655 . . . ? S3 Cd1 S2 C18 66.16(14) . . . . ? N3 Cd1 S3 C19 29.73(16) . . . . ? N5 Cd1 S3 C19 138.5(6) 7_655 . . . ? N4 Cd1 S3 C19 122.12(17) 7_655 . . . ? S1 Cd1 S3 C19 -147.76(14) 7_655 . . . ? S2 Cd1 S3 C19 -63.43(14) . . . . ? N5 Cd1 N3 C17 145.8(8) 7_655 . . . ? N4 Cd1 N3 C17 -130.3(8) 7_655 . . . ? S1 Cd1 N3 C17 -2.8(19) 7_655 . . . ? S2 Cd1 N3 C17 51.4(8) . . . . ? S3 Cd1 N3 C17 -42.2(7) . . . . ? C1 N1 C3 C8 9.0(6) . . . . ? C2 N1 C3 C8 -179.2(4) . . . . ? C1 N1 C3 C4 -170.9(4) . . . . ? C2 N1 C3 C4 0.9(7) . . . . ? N1 C3 C4 C5 178.4(4) . . . . ? C8 C3 C4 C5 -1.5(7) . . . . ? C3 C4 C5 C6 0.5(7) . . . . ? C4 C5 C6 C7 1.0(6) . . . . ? C4 C5 C6 C9 -178.5(4) . . . . ? C5 C6 C7 C8 -1.5(7) . . . . ? C9 C6 C7 C8 178.0(4) . . . . ? C6 C7 C8 C3 0.5(8) . . . . ? N1 C3 C8 C7 -178.9(4) . . . . ? C4 C3 C8 C7 1.0(7) . . . . ? C7 C6 C9 C10 -172.3(4) . . . . ? C5 C6 C9 C10 7.2(7) . . . . ? C6 C9 C10 C11 178.5(4) . . . . ? C9 C10 C11 C12 -164.3(4) . . . . ? C9 C10 C11 C15 17.8(7) . . . . ? C15 C11 C12 C13 -2.2(6) . . . . ? C10 C11 C12 C13 179.7(4) . . . . ? C11 C12 C13 N2 0.8(6) . . . . ? C14 N2 C13 C12 1.5(6) . . . . ? C16 N2 C13 C12 -177.6(4) . . . . ? C13 N2 C14 C15 -2.3(7) . . . . ? C16 N2 C14 C15 176.8(4) . . . . ? N2 C14 C15 C11 0.8(7) . . . . ? C12 C11 C15 C14 1.4(7) . . . . ? C10 C11 C15 C14 179.4(4) . . . . ? Cd1 N3 C17 S1 152(100) . . . . ? Cd1 S1 C17 N3 -160(100) 7_665 . . . ? Cd1 N5 C18 S2 -157(22) 7_665 . . . ? Cd1 S2 C18 N5 127(22) . . . . ? Cd1 N4 C19 S3 157(17) 7_665 . . . ? Cd1 S3 C19 N4 -139(18) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.732 _refine_diff_density_min -1.594 _refine_diff_density_rms 0.189 data_2-SCN _database_code_depnum_ccdc_archive 'CCDC 246083' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H26 Cd N6 S3' _chemical_formula_weight 595.08 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' Cd Cd -0.8075 1.2024 '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 12.906(2) _cell_length_b 10.8887(16) _cell_length_c 19.289(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.610(14) _cell_angle_gamma 90.00 _cell_volume 2697.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 53 _cell_measurement_theta_min 5.26 _cell_measurement_theta_max 12.52 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 1.064 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.7204 _exptl_absorpt_correction_T_max 0.8075 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number 97 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% . _diffrn_reflns_number 6010 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4734 _reflns_number_gt 3529 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0613P)^2^+0.0000P] 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 0.0021(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4734 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1116 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 Cd1 Cd 0.24203(3) 0.54282(3) 0.228185(18) 0.04605(15) Uani 1 1 d . . . S1 S 0.14265(10) 0.68308(11) 0.12401(7) 0.0563(3) Uani 1 1 d . . . S2 S 0.05952(10) 0.41333(11) 0.21095(8) 0.0602(4) Uani 1 1 d . . . S3 S 0.32739(12) 0.40826(11) 0.12956(7) 0.0645(4) Uani 1 1 d . . . N1 N -0.0308(3) 1.4615(3) 0.39880(19) 0.0484(9) Uani 1 1 d . . . N2 N 0.2865(3) 0.7307(4) 0.7249(2) 0.0635(11) Uani 1 1 d . . . N4 N 0.1173(3) 0.1791(3) 0.2609(2) 0.0638(12) Uani 1 1 d . . . N5 N 0.3251(3) 0.1750(3) 0.1896(2) 0.0625(11) Uani 1 1 d . . . N3 N 0.1972(3) 0.9101(3) 0.1852(2) 0.0523(10) Uani 1 1 d . . . N6 N 0.6829(7) 0.4818(11) 0.4967(5) 0.179(4) Uani 1 1 d . . . C1 C -0.0637(5) 1.5689(4) 0.3557(3) 0.0656(14) Uani 1 1 d . . . H1A H -0.0431 1.6427 0.3806 0.098 Uiso 1 1 calc R . . H1B H -0.1380 1.5679 0.3456 0.098 Uiso 1 1 calc R . . H1C H -0.0314 1.5661 0.3130 0.098 Uiso 1 1 calc R . . C2 C 0.0666(4) 1.4193(4) 0.3988(3) 0.0543(12) Uani 1 1 d . . . H2A H 0.1127 1.4582 0.3718 0.065 Uiso 1 1 calc R . . C3 C 0.0990(4) 1.3192(4) 0.4383(2) 0.0532(12) Uani 1 1 d . . . H3C H 0.1671 1.2914 0.4381 0.064 Uiso 1 1 calc R . . C4 C 0.0309(4) 1.2580(4) 0.4790(2) 0.0459(10) Uani 1 1 d . . . C5 C -0.0689(4) 1.3073(4) 0.4773(2) 0.0511(11) Uani 1 1 d . . . H5C H -0.1169 1.2711 0.5039 0.061 Uiso 1 1 calc R . . C6 C -0.0980(4) 1.4071(4) 0.4376(2) 0.0524(12) Uani 1 1 d . . . H6A H -0.1653 1.4379 0.4374 0.063 Uiso 1 1 calc R . . C7 C 0.0586(4) 1.1530(4) 0.5221(2) 0.0500(11) Uani 1 1 d . . . H7A H 0.0079 1.1229 0.5486 0.060 Uiso 1 1 calc R . . C8 C 0.1494(4) 1.0950(4) 0.5277(2) 0.0483(11) Uani 1 1 d . . . H8A H 0.1983 1.1207 0.4985 0.058 Uiso 1 1 calc R . . C9 C 0.1795(4) 0.9953(4) 0.5752(2) 0.0476(11) Uani 1 1 d . . . C10 C 0.2808(4) 0.9486(4) 0.5791(3) 0.0576(12) Uani 1 1 d . . . H10A H 0.3258 0.9772 0.5478 0.069 Uiso 1 1 calc R . . C11 C 0.3163(4) 0.8620(4) 0.6276(3) 0.0550(12) Uani 1 1 d . . . H11A H 0.3846 0.8341 0.6288 0.066 Uiso 1 1 calc R . . C12 C 0.2512(4) 0.8151(4) 0.6751(2) 0.0505(11) Uani 1 1 d . . . C13 C 0.1482(3) 0.8585(4) 0.6703(2) 0.0481(11) Uani 1 1 d . . . H13A H 0.1020 0.8276 0.7001 0.058 Uiso 1 1 calc R . . C14 C 0.1151(3) 0.9460(4) 0.6219(2) 0.0482(11) Uani 1 1 d . . . H14A H 0.0468 0.9735 0.6203 0.058 Uiso 1 1 calc R . . C15 C 0.3945(4) 0.6888(4) 0.7343(3) 0.0624(14) Uani 1 1 d . . . H15A H 0.4118 0.6652 0.7826 0.075 Uiso 1 1 calc R . . H15B H 0.4401 0.7559 0.7241 0.075 Uiso 1 1 calc R . . C16 C 0.4127(5) 0.5831(5) 0.6886(4) 0.0869(19) Uani 1 1 d . . . H16A H 0.4843 0.5581 0.6964 0.130 Uiso 1 1 calc R . . H16B H 0.3972 0.6068 0.6408 0.130 Uiso 1 1 calc R . . H16C H 0.3685 0.5161 0.6991 0.130 Uiso 1 1 calc R . . C17 C 0.2141(4) 0.6707(4) 0.7677(3) 0.0593(13) Uani 1 1 d . . . H17A H 0.2416 0.5904 0.7811 0.071 Uiso 1 1 calc R . . H17B H 0.1485 0.6582 0.7394 0.071 Uiso 1 1 calc R . . C18 C 0.1927(4) 0.7390(5) 0.8325(3) 0.0715(15) Uani 1 1 d . . . H18A H 0.1445 0.6930 0.8571 0.107 Uiso 1 1 calc R . . H18B H 0.1633 0.8179 0.8200 0.107 Uiso 1 1 calc R . . H18C H 0.2565 0.7498 0.8618 0.107 Uiso 1 1 calc R . . C20 C 0.0955(3) 0.2762(4) 0.2405(2) 0.0483(11) Uani 1 1 d . . . C21 C 0.3257(4) 0.2713(4) 0.1649(2) 0.0486(11) Uani 1 1 d . . . C19 C 0.1745(3) 0.8171(4) 0.1604(2) 0.0441(10) Uani 1 1 d . . . C22 C 0.6315(8) 0.4149(12) 0.5258(5) 0.129(4) Uani 1 1 d . . . C23 C 0.5648(8) 0.3322(10) 0.5593(5) 0.178(5) Uani 1 1 d . . . H23A H 0.4950 0.3384 0.5372 0.268 Uiso 1 1 calc R . . H23B H 0.5656 0.3535 0.6076 0.268 Uiso 1 1 calc R . . H23C H 0.5894 0.2495 0.5552 0.268 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 Cd1 0.0493(2) 0.02855(18) 0.0613(2) 0.00080(15) 0.01056(15) -0.00072(15) S1 0.0632(8) 0.0379(6) 0.0662(8) -0.0054(5) -0.0017(6) -0.0041(6) S2 0.0465(7) 0.0417(6) 0.0914(10) 0.0058(6) 0.0023(7) -0.0030(5) S3 0.0887(10) 0.0390(6) 0.0725(9) 0.0082(6) 0.0415(8) 0.0078(6) N1 0.058(2) 0.0359(19) 0.051(2) 0.0040(17) 0.0047(19) 0.0060(18) N2 0.042(2) 0.058(2) 0.090(3) 0.031(2) 0.004(2) 0.006(2) N4 0.057(3) 0.034(2) 0.099(3) -0.003(2) 0.004(2) 0.0066(19) N5 0.080(3) 0.038(2) 0.073(3) -0.001(2) 0.024(2) 0.006(2) N3 0.062(3) 0.035(2) 0.059(2) 0.0001(18) 0.001(2) 0.0046(19) N6 0.112(7) 0.302(13) 0.128(7) -0.040(8) 0.033(5) -0.015(8) C1 0.084(4) 0.044(3) 0.070(3) 0.009(2) 0.014(3) 0.022(3) C2 0.053(3) 0.050(3) 0.062(3) 0.008(2) 0.016(2) 0.006(2) C3 0.050(3) 0.049(3) 0.061(3) 0.001(2) 0.006(2) 0.014(2) C4 0.056(3) 0.041(2) 0.040(2) -0.0017(19) 0.000(2) 0.001(2) C5 0.046(3) 0.051(3) 0.058(3) 0.008(2) 0.007(2) -0.004(2) C6 0.045(3) 0.055(3) 0.057(3) -0.004(2) 0.004(2) 0.009(2) C7 0.053(3) 0.047(3) 0.050(3) 0.003(2) 0.002(2) 0.003(2) C8 0.054(3) 0.046(2) 0.044(3) -0.006(2) 0.001(2) 0.002(2) C9 0.052(3) 0.041(2) 0.047(3) -0.006(2) -0.009(2) 0.004(2) C10 0.060(3) 0.050(3) 0.063(3) 0.008(2) 0.008(2) 0.001(2) C11 0.044(3) 0.050(3) 0.072(3) 0.008(2) 0.010(2) 0.010(2) C12 0.044(3) 0.043(2) 0.062(3) 0.003(2) -0.005(2) 0.004(2) C13 0.044(3) 0.045(3) 0.053(3) 0.000(2) -0.004(2) 0.000(2) C14 0.040(2) 0.045(3) 0.058(3) -0.008(2) -0.003(2) 0.007(2) C15 0.049(3) 0.054(3) 0.083(4) 0.016(3) -0.001(3) -0.001(2) C16 0.084(4) 0.057(3) 0.121(5) -0.006(4) 0.011(4) 0.005(3) C17 0.050(3) 0.045(3) 0.081(4) 0.010(3) 0.000(3) 0.004(2) C18 0.063(3) 0.064(3) 0.085(4) 0.015(3) -0.005(3) -0.009(3) C20 0.035(2) 0.041(3) 0.069(3) -0.005(2) 0.006(2) -0.004(2) C21 0.051(3) 0.040(3) 0.057(3) -0.008(2) 0.017(2) 0.001(2) C19 0.047(3) 0.037(2) 0.048(3) 0.004(2) 0.004(2) 0.007(2) C22 0.090(6) 0.207(12) 0.088(6) -0.022(7) 0.002(5) 0.025(7) C23 0.167(10) 0.207(12) 0.164(9) 0.073(9) 0.033(8) 0.006(9) _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 Cd1 N3 2.288(4) 2_545 ? Cd1 N4 2.338(4) 2 ? Cd1 N5 2.368(4) 2 ? Cd1 S3 2.7183(14) . ? Cd1 S2 2.7374(13) . ? Cd1 S1 2.7407(13) . ? S1 C19 1.654(4) . ? S2 C20 1.649(5) . ? S3 C21 1.641(5) . ? N1 C6 1.337(6) . ? N1 C2 1.338(6) . ? N1 C1 1.473(5) . ? N2 C12 1.374(6) . ? N2 C17 1.460(6) . ? N2 C15 1.462(6) . ? N4 C20 1.153(5) . ? N4 Cd1 2.338(4) 2_545 ? N5 C21 1.152(5) . ? N5 Cd1 2.368(4) 2_545 ? N3 C19 1.146(5) . ? N3 Cd1 2.288(4) 2 ? N6 C22 1.166(13) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.372(6) . ? C2 H2A 0.9300 . ? C3 C4 1.403(6) . ? C3 H3C 0.9300 . ? C4 C5 1.392(6) . ? C4 C7 1.438(6) . ? C5 C6 1.361(6) . ? C5 H5C 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.326(6) . ? C7 H7A 0.9300 . ? C8 C9 1.449(6) . ? C8 H8A 0.9300 . ? C9 C14 1.392(7) . ? C9 C10 1.398(7) . ? C10 C11 1.375(6) . ? C10 H10A 0.9300 . ? C11 C12 1.399(6) . ? C11 H11A 0.9300 . ? C12 C13 1.406(6) . ? C13 C14 1.372(6) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.483(7) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.504(7) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C22 C23 1.441(12) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 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 N3 Cd1 N4 97.32(14) 2_545 2 ? N3 Cd1 N5 90.94(14) 2_545 2 ? N4 Cd1 N5 83.42(15) 2 2 ? N3 Cd1 S3 92.13(10) 2_545 . ? N4 Cd1 S3 92.34(12) 2 . ? N5 Cd1 S3 175.05(10) 2 . ? N3 Cd1 S2 89.59(10) 2_545 . ? N4 Cd1 S2 171.52(10) 2 . ? N5 Cd1 S2 91.60(11) 2 . ? S3 Cd1 S2 92.30(5) . . ? N3 Cd1 S1 171.67(10) 2_545 . ? N4 Cd1 S1 90.91(11) 2 . ? N5 Cd1 S1 88.67(11) 2 . ? S3 Cd1 S1 88.85(4) . . ? S2 Cd1 S1 82.10(4) . . ? C19 S1 Cd1 95.81(15) . . ? C20 S2 Cd1 102.40(16) . . ? C21 S3 Cd1 100.20(16) . . ? C6 N1 C2 120.6(4) . . ? C6 N1 C1 120.0(4) . . ? C2 N1 C1 119.5(4) . . ? C12 N2 C17 120.5(4) . . ? C12 N2 C15 122.9(4) . . ? C17 N2 C15 116.4(4) . . ? C20 N4 Cd1 140.7(4) . 2_545 ? C21 N5 Cd1 148.1(4) . 2_545 ? C19 N3 Cd1 156.6(3) . 2 ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 120.6(5) . . ? N1 C2 H2A 119.7 . . ? C3 C2 H2A 119.7 . . ? C2 C3 C4 120.9(5) . . ? C2 C3 H3C 119.5 . . ? C4 C3 H3C 119.5 . . ? C5 C4 C3 115.6(4) . . ? C5 C4 C7 119.8(4) . . ? C3 C4 C7 124.5(4) . . ? C6 C5 C4 121.6(4) . . ? C6 C5 H5C 119.2 . . ? C4 C5 H5C 119.2 . . ? N1 C6 C5 120.6(4) . . ? N1 C6 H6A 119.7 . . ? C5 C6 H6A 119.7 . . ? C8 C7 C4 126.5(5) . . ? C8 C7 H7A 116.8 . . ? C4 C7 H7A 116.8 . . ? C7 C8 C9 126.2(5) . . ? C7 C8 H8A 116.9 . . ? C9 C8 H8A 116.9 . . ? C14 C9 C10 116.0(4) . . ? C14 C9 C8 123.9(4) . . ? C10 C9 C8 119.9(5) . . ? C11 C10 C9 122.2(5) . . ? C11 C10 H10A 118.9 . . ? C9 C10 H10A 118.9 . . ? C10 C11 C12 121.0(4) . . ? C10 C11 H11A 119.5 . . ? C12 C11 H11A 119.5 . . ? N2 C12 C11 121.6(4) . . ? N2 C12 C13 121.1(4) . . ? C11 C12 C13 117.3(4) . . ? C14 C13 C12 120.5(4) . . ? C14 C13 H13A 119.8 . . ? C12 C13 H13A 119.8 . . ? C13 C14 C9 122.9(4) . . ? C13 C14 H14A 118.6 . . ? C9 C14 H14A 118.6 . . ? N2 C15 C16 111.9(5) . . ? N2 C15 H15A 109.2 . . ? C16 C15 H15A 109.2 . . ? N2 C15 H15B 109.2 . . ? C16 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 C17 C18 115.4(4) . . ? N2 C17 H17A 108.4 . . ? C18 C17 H17A 108.4 . . ? N2 C17 H17B 108.4 . . ? C18 C17 H17B 108.4 . . ? H17A C17 H17B 107.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N4 C20 S2 177.8(4) . . ? N5 C21 S3 179.7(5) . . ? N3 C19 S1 179.4(5) . . ? N6 C22 C23 177.6(11) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.410 _refine_diff_density_min -0.589 _refine_diff_density_rms 0.099 data_4-SCN _database_code_depnum_ccdc_archive 'CCDC 246084' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H31 Cd N5 S3' _chemical_formula_weight 610.13 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' Cd Cd -0.8075 1.2024 '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 12.7935(16) _cell_length_b 10.7453(15) _cell_length_c 20.771(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.639(11) _cell_angle_gamma 90.00 _cell_volume 2815.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 29 _cell_measurement_theta_min 5.12 _cell_measurement_theta_max 12.49 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 1.020 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7360 _exptl_absorpt_correction_T_max 0.9048 _exptl_absorpt_process_details sadads _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% multiscan _diffrn_reflns_number 6327 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4956 _reflns_number_gt 3320 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0421P)^2^+0.0317P] 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 contr _refine_ls_extinction_method none _refine_ls_extinction_coef 0.0029(2) _refine_ls_number_reflns 4956 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0730 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.0959 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.005 _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 Cd1 Cd 0.21476(2) 0.74603(3) 0.248782(14) 0.04671(12) Uani 1 1 d . . . N1 N 0.0525(3) -0.2239(3) 0.95642(17) 0.0484(9) Uani 1 1 d . . . N2 N 0.3697(4) 0.7009(4) 0.9645(2) 0.0874(15) Uani 1 1 d . . . N3 N 0.1516(3) 1.1141(3) 0.26338(18) 0.0574(10) Uani 1 1 d . . . N4 N 0.1618(3) 0.3777(3) 0.18589(17) 0.0594(11) Uani 1 1 d . . . N5 N 0.2645(3) 0.3819(3) 0.33556(17) 0.0617(11) Uani 1 1 d . . . S1 S 0.05328(10) 0.88634(11) 0.27798(6) 0.0609(3) Uani 1 1 d . . . S2 S 0.07532(11) 0.61400(11) 0.16023(6) 0.0718(4) Uani 1 1 d . . . S3 S 0.17090(11) 0.61227(11) 0.35372(6) 0.0620(3) Uani 1 1 d . . . C1 C 0.0299(4) -0.3565(4) 0.9650(2) 0.0623(13) Uani 1 1 d . . . H1A H -0.0406 -0.3750 0.9433 0.093 Uiso 1 1 calc R . . H1B H 0.0357 -0.3747 1.0107 0.093 Uiso 1 1 calc R . . H1C H 0.0799 -0.4062 0.9466 0.093 Uiso 1 1 calc R . . C2 C 0.1198(3) -0.1648(4) 1.0049(2) 0.0502(11) Uani 1 1 d . . . H2A H 0.1481 -0.2073 1.0428 0.060 Uiso 1 1 calc R . . C3 C 0.1451(3) -0.0439(4) 0.9972(2) 0.0500(11) Uani 1 1 d . . . H3C H 0.1920 -0.0055 1.0302 0.060 Uiso 1 1 calc R . . C4 C 0.1040(3) 0.0260(4) 0.9418(2) 0.0477(11) Uani 1 1 d . . . C5 C 0.0343(4) -0.0397(4) 0.8942(2) 0.0553(12) Uani 1 1 d . . . H5C H 0.0039 0.0007 0.8560 0.066 Uiso 1 1 calc R . . C6 C 0.0109(3) -0.1600(4) 0.9028(2) 0.0551(12) Uani 1 1 d . . . H6A H -0.0359 -0.2003 0.8704 0.066 Uiso 1 1 calc R . . C7 C 0.1328(3) 0.1522(4) 0.9324(2) 0.0470(10) Uani 1 1 d . . . H7A H 0.1119 0.1863 0.8911 0.056 Uiso 1 1 calc R . . C8 C 0.1876(4) 0.2255(4) 0.9784(2) 0.0535(12) Uani 1 1 d . . . H8A H 0.2025 0.1903 1.0198 0.064 Uiso 1 1 calc R . . C9 C 0.2269(3) 0.3501(4) 0.9737(2) 0.0467(10) Uani 1 1 d . . . C10 C 0.2750(4) 0.4115(4) 1.0300(2) 0.0566(12) Uani 1 1 d . . . H10A H 0.2763 0.3722 1.0700 0.068 Uiso 1 1 calc R . . C11 C 0.3208(4) 0.5275(5) 1.0293(2) 0.0685(14) Uani 1 1 d . . . H11A H 0.3503 0.5663 1.0681 0.082 Uiso 1 1 calc R . . C12 C 0.3220(4) 0.5870(5) 0.9684(3) 0.0674(14) Uani 1 1 d . . . C13 C 0.2723(4) 0.5259(4) 0.9119(2) 0.0616(13) Uani 1 1 d . . . H13A H 0.2706 0.5639 0.8715 0.074 Uiso 1 1 calc R . . C14 C 0.2265(4) 0.4123(4) 0.9147(2) 0.0573(12) Uani 1 1 d . . . H14A H 0.1938 0.3749 0.8762 0.069 Uiso 1 1 calc R . . C15 C 0.3903(5) 0.7498(5) 0.9023(3) 0.098(2) Uani 1 1 d . . . H15A H 0.4022 0.6810 0.8743 0.117 Uiso 1 1 calc R . . H15B H 0.4543 0.7998 0.9100 0.117 Uiso 1 1 calc R . . C16 C 0.3008(5) 0.8275(5) 0.8683(3) 0.0884(18) Uani 1 1 d . . . H16A H 0.2930 0.9003 0.8947 0.106 Uiso 1 1 calc R . . H16B H 0.2356 0.7799 0.8643 0.106 Uiso 1 1 calc R . . C17 C 0.3173(6) 0.8693(7) 0.8006(3) 0.116(2) Uani 1 1 d . . . H17A H 0.3864 0.9082 0.8039 0.140 Uiso 1 1 calc R . . H17B H 0.3163 0.7970 0.7725 0.140 Uiso 1 1 calc R . . C18 C 0.2349(7) 0.9582(9) 0.7708(4) 0.167(4) Uani 1 1 d . . . H18A H 0.2488 0.9832 0.7287 0.251 Uiso 1 1 calc R . . H18B H 0.2358 1.0301 0.7983 0.251 Uiso 1 1 calc R . . H18C H 0.1665 0.9191 0.7660 0.251 Uiso 1 1 calc R . . C19 C 0.4063(5) 0.7833(6) 1.0257(4) 0.113(2) Uani 1 1 d . . . H19A H 0.3978 0.8711 1.0151 0.136 Uiso 1 1 calc R . . H19B H 0.3668 0.7638 1.0604 0.136 Uiso 1 1 calc R . . C20 C 0.5162(6) 0.7515(7) 1.0441(5) 0.147(3) Uani 1 1 d . . . H20A H 0.5546 0.7676 1.0084 0.177 Uiso 1 1 calc R . . H20B H 0.5240 0.6642 1.0559 0.177 Uiso 1 1 calc R . . C21 C 0.5605(6) 0.8408(8) 1.1073(4) 0.142(3) Uani 1 1 d . . . H21A H 0.6370 0.8483 1.1119 0.170 Uiso 1 1 calc R . . H21B H 0.5302 0.9233 1.1000 0.170 Uiso 1 1 calc R . . C22 C 0.5335(7) 0.7902(8) 1.1660(4) 0.154(4) Uani 1 1 d . . . H22A H 0.5578 0.8452 1.2018 0.231 Uiso 1 1 calc R . . H22B H 0.5665 0.7103 1.1744 0.231 Uiso 1 1 calc R . . H22C H 0.4579 0.7812 1.1611 0.231 Uiso 1 1 calc R . . C23 C 0.1116(3) 1.0207(4) 0.2696(2) 0.0490(11) Uani 1 1 d . . . C24 C 0.1267(4) 0.4747(4) 0.1763(2) 0.0519(12) Uani 1 1 d . . . C25 C 0.2257(4) 0.4774(4) 0.34225(18) 0.0470(11) 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 Cd1 0.0589(2) 0.02920(16) 0.04770(18) 0.00124(16) -0.00369(13) 0.00062(17) N1 0.048(2) 0.045(2) 0.051(2) -0.0038(17) 0.0055(17) -0.0014(17) N2 0.103(4) 0.071(3) 0.088(3) -0.007(3) 0.016(3) -0.043(3) N3 0.058(2) 0.037(2) 0.076(3) -0.001(2) 0.005(2) 0.002(2) N4 0.073(3) 0.0314(19) 0.063(2) 0.0003(18) -0.019(2) 0.001(2) N5 0.094(3) 0.037(2) 0.055(2) -0.0005(19) 0.015(2) 0.007(2) S1 0.0625(8) 0.0406(6) 0.0822(9) 0.0107(6) 0.0194(7) -0.0009(6) S2 0.0860(9) 0.0389(6) 0.0752(8) -0.0061(6) -0.0312(7) 0.0087(7) S3 0.0896(10) 0.0433(6) 0.0536(7) 0.0041(6) 0.0130(7) 0.0161(7) C1 0.063(3) 0.048(3) 0.073(3) -0.011(2) 0.002(3) -0.016(3) C2 0.054(3) 0.053(3) 0.041(2) 0.004(2) -0.001(2) 0.000(2) C3 0.053(3) 0.051(3) 0.043(2) -0.010(2) -0.001(2) -0.007(2) C4 0.049(3) 0.050(3) 0.046(2) 0.004(2) 0.013(2) 0.007(2) C5 0.061(3) 0.055(3) 0.047(3) -0.001(2) 0.001(2) -0.006(3) C6 0.057(3) 0.058(3) 0.043(2) -0.005(2) -0.013(2) -0.005(3) C7 0.048(3) 0.049(2) 0.039(2) 0.001(2) -0.0063(19) -0.001(2) C8 0.054(3) 0.053(3) 0.056(3) 0.002(2) 0.015(2) 0.004(2) C9 0.046(2) 0.045(2) 0.048(2) -0.003(2) 0.003(2) -0.001(2) C10 0.059(3) 0.063(3) 0.045(2) 0.007(2) -0.001(2) -0.008(3) C11 0.074(3) 0.064(3) 0.063(3) -0.006(3) -0.002(3) -0.022(3) C12 0.064(3) 0.058(3) 0.083(4) 0.004(3) 0.021(3) -0.005(3) C13 0.082(4) 0.052(3) 0.053(3) 0.005(2) 0.015(3) -0.007(3) C14 0.067(3) 0.049(3) 0.057(3) 0.005(2) 0.014(2) 0.002(3) C15 0.094(4) 0.073(4) 0.137(6) 0.004(4) 0.053(4) -0.021(4) C16 0.092(4) 0.075(4) 0.103(5) -0.009(4) 0.033(4) -0.007(4) C17 0.155(7) 0.106(5) 0.098(5) 0.001(4) 0.050(5) 0.006(5) C18 0.217(10) 0.176(9) 0.099(5) 0.000(6) -0.004(6) 0.028(8) C19 0.083(5) 0.098(5) 0.165(7) 0.030(5) 0.038(5) 0.016(4) C20 0.098(6) 0.129(7) 0.223(10) -0.007(7) 0.047(6) 0.022(6) C21 0.118(6) 0.139(7) 0.172(8) -0.033(7) 0.034(6) -0.047(6) C22 0.144(8) 0.152(8) 0.168(8) 0.034(7) 0.033(7) -0.034(6) C23 0.052(3) 0.036(2) 0.059(3) 0.003(2) 0.012(2) 0.009(2) C24 0.059(3) 0.043(3) 0.048(3) -0.007(2) -0.008(2) -0.015(2) C25 0.061(3) 0.043(2) 0.031(2) 0.0053(19) -0.009(2) -0.005(2) _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 Cd1 N3 2.268(4) 2_545 ? Cd1 N5 2.330(4) 2 ? Cd1 N4 2.371(3) 2 ? Cd1 S1 2.7071(13) . ? Cd1 S2 2.7349(12) . ? Cd1 S3 2.7460(13) . ? N1 C6 1.339(5) . ? N1 C2 1.366(5) . ? N1 C1 1.471(5) . ? N2 C12 1.376(6) . ? N2 C15 1.459(7) . ? N2 C19 1.556(8) . ? N3 C23 1.143(5) . ? N3 Cd1 2.268(4) 2 ? N4 C24 1.139(5) . ? N4 Cd1 2.371(3) 2_545 ? N5 C25 1.159(5) . ? N5 Cd1 2.330(4) 2_545 ? S1 C23 1.648(5) . ? S2 C24 1.647(5) . ? S3 C25 1.644(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.355(6) . ? C2 H2A 0.9300 . ? C3 C4 1.400(5) . ? C3 H3C 0.9300 . ? C4 C5 1.405(6) . ? C4 C7 1.428(6) . ? C5 C6 1.346(6) . ? C5 H5C 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.342(6) . ? C7 H7A 0.9300 . ? C8 C9 1.439(6) . ? C8 H8A 0.9300 . ? C9 C14 1.393(6) . ? C9 C10 1.394(5) . ? C10 C11 1.379(6) . ? C10 H10A 0.9300 . ? C11 C12 1.419(7) . ? C11 H11A 0.9300 . ? C12 C13 1.402(6) . ? C13 C14 1.360(6) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.495(8) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.525(7) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.480(9) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.434(9) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.649(10) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.428(9) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 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 N3 Cd1 N5 97.20(14) 2_545 2 ? N3 Cd1 N4 89.67(13) 2_545 2 ? N5 Cd1 N4 84.69(13) 2 2 ? N3 Cd1 S1 172.36(10) 2_545 . ? N5 Cd1 S1 90.37(10) 2 . ? N4 Cd1 S1 89.99(10) 2 . ? N3 Cd1 S2 91.14(9) 2_545 . ? N5 Cd1 S2 87.87(10) 2 . ? N4 Cd1 S2 172.57(9) 2 . ? S1 Cd1 S2 90.19(4) . . ? N3 Cd1 S3 91.11(10) 2_545 . ? N5 Cd1 S3 171.51(10) 2 . ? N4 Cd1 S3 93.62(10) 2 . ? S1 Cd1 S3 81.30(4) . . ? S2 Cd1 S3 93.75(4) . . ? C6 N1 C2 119.2(4) . . ? C6 N1 C1 122.5(4) . . ? C2 N1 C1 118.2(4) . . ? C12 N2 C15 121.4(5) . . ? C12 N2 C19 122.3(5) . . ? C15 N2 C19 116.3(5) . . ? C23 N3 Cd1 157.1(3) . 2 ? C24 N4 Cd1 148.3(3) . 2_545 ? C25 N5 Cd1 138.6(3) . 2_545 ? C23 S1 Cd1 95.05(15) . . ? C24 S2 Cd1 98.15(14) . . ? C25 S3 Cd1 101.39(15) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 N1 119.4(4) . . ? C3 C2 H2A 120.3 . . ? N1 C2 H2A 120.3 . . ? C2 C3 C4 123.2(4) . . ? C2 C3 H3C 118.4 . . ? C4 C3 H3C 118.4 . . ? C3 C4 C5 114.5(4) . . ? C3 C4 C7 123.5(4) . . ? C5 C4 C7 121.9(4) . . ? C6 C5 C4 121.2(4) . . ? C6 C5 H5C 119.4 . . ? C4 C5 H5C 119.4 . . ? N1 C6 C5 122.4(4) . . ? N1 C6 H6A 118.8 . . ? C5 C6 H6A 118.8 . . ? C8 C7 C4 125.2(4) . . ? C8 C7 H7A 117.4 . . ? C4 C7 H7A 117.4 . . ? C7 C8 C9 130.2(4) . . ? C7 C8 H8A 114.9 . . ? C9 C8 H8A 114.9 . . ? C14 C9 C10 116.6(4) . . ? C14 C9 C8 123.7(4) . . ? C10 C9 C8 119.6(4) . . ? C11 C10 C9 123.2(4) . . ? C11 C10 H10A 118.4 . . ? C9 C10 H10A 118.4 . . ? C10 C11 C12 119.0(5) . . ? C10 C11 H11A 120.5 . . ? C12 C11 H11A 120.5 . . ? N2 C12 C13 120.7(5) . . ? N2 C12 C11 121.6(5) . . ? C13 C12 C11 117.7(5) . . ? C14 C13 C12 121.5(5) . . ? C14 C13 H13A 119.3 . . ? C12 C13 H13A 119.3 . . ? C13 C14 C9 122.1(5) . . ? C13 C14 H14A 119.0 . . ? C9 C14 H14A 119.0 . . ? N2 C15 C16 112.5(5) . . ? N2 C15 H15A 109.1 . . ? C16 C15 H15A 109.1 . . ? N2 C15 H15B 109.1 . . ? C16 C15 H15B 109.1 . . ? H15A C15 H15B 107.8 . . ? C15 C16 C17 112.8(6) . . ? C15 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? C15 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C18 C17 C16 112.2(6) . . ? C18 C17 H17A 109.2 . . ? C16 C17 H17A 109.2 . . ? C18 C17 H17B 109.2 . . ? C16 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 N2 103.2(6) . . ? C20 C19 H19A 111.1 . . ? N2 C19 H19A 111.1 . . ? C20 C19 H19B 111.1 . . ? N2 C19 H19B 111.1 . . ? H19A C19 H19B 109.1 . . ? C19 C20 C21 105.3(7) . . ? C19 C20 H20A 110.7 . . ? C21 C20 H20A 110.7 . . ? C19 C20 H20B 110.7 . . ? C21 C20 H20B 110.7 . . ? H20A C20 H20B 108.8 . . ? C22 C21 C20 111.0(7) . . ? C22 C21 H21A 109.4 . . ? C20 C21 H21A 109.4 . . ? C22 C21 H21B 109.4 . . ? C20 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N3 C23 S1 179.5(5) . . ? N4 C24 S2 178.4(4) . . ? N5 C25 S3 178.6(4) . . ? 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 N3 Cd1 S1 C23 130.1(7) 2_545 . . . ? N5 Cd1 S1 C23 -42.02(19) 2 . . . ? N4 Cd1 S1 C23 42.67(18) 2 . . . ? S2 Cd1 S1 C23 -129.90(16) . . . . ? S3 Cd1 S1 C23 136.34(16) . . . . ? N3 Cd1 S2 C24 32.9(2) 2_545 . . . ? N5 Cd1 S2 C24 130.0(2) 2 . . . ? N4 Cd1 S2 C24 129.0(8) 2 . . . ? S1 Cd1 S2 C24 -139.62(18) . . . . ? S3 Cd1 S2 C24 -58.33(18) . . . . ? N3 Cd1 S3 C25 -20.40(17) 2_545 . . . ? N5 Cd1 S3 C25 171.6(7) 2 . . . ? N4 Cd1 S3 C25 -110.13(18) 2 . . . ? S1 Cd1 S3 C25 160.43(15) . . . . ? S2 Cd1 S3 C25 70.81(15) . . . . ? C6 N1 C2 C3 -1.5(6) . . . . ? C1 N1 C2 C3 177.6(4) . . . . ? N1 C2 C3 C4 1.1(7) . . . . ? C2 C3 C4 C5 -0.3(7) . . . . ? C2 C3 C4 C7 -177.9(4) . . . . ? C3 C4 C5 C6 0.0(7) . . . . ? C7 C4 C5 C6 177.6(4) . . . . ? C2 N1 C6 C5 1.2(7) . . . . ? C1 N1 C6 C5 -177.9(4) . . . . ? C4 C5 C6 N1 -0.4(8) . . . . ? C3 C4 C7 C8 -11.5(7) . . . . ? C5 C4 C7 C8 171.1(4) . . . . ? C4 C7 C8 C9 175.4(4) . . . . ? C7 C8 C9 C14 -9.6(8) . . . . ? C7 C8 C9 C10 174.8(5) . . . . ? C14 C9 C10 C11 -0.2(7) . . . . ? C8 C9 C10 C11 175.7(4) . . . . ? C9 C10 C11 C12 -1.8(8) . . . . ? C15 N2 C12 C13 -13.2(8) . . . . ? C19 N2 C12 C13 168.0(5) . . . . ? C15 N2 C12 C11 167.2(5) . . . . ? C19 N2 C12 C11 -11.7(8) . . . . ? C10 C11 C12 N2 -177.8(5) . . . . ? C10 C11 C12 C13 2.6(8) . . . . ? N2 C12 C13 C14 178.8(5) . . . . ? C11 C12 C13 C14 -1.5(8) . . . . ? C12 C13 C14 C9 -0.4(8) . . . . ? C10 C9 C14 C13 1.3(7) . . . . ? C8 C9 C14 C13 -174.4(4) . . . . ? C12 N2 C15 C16 91.0(7) . . . . ? C19 N2 C15 C16 -90.1(6) . . . . ? N2 C15 C16 C17 -174.8(5) . . . . ? C15 C16 C17 C18 -173.1(6) . . . . ? C12 N2 C19 C20 95.1(7) . . . . ? C15 N2 C19 C20 -83.8(7) . . . . ? N2 C19 C20 C21 177.8(5) . . . . ? C19 C20 C21 C22 80.8(9) . . . . ? Cd1 N3 C23 S1 -126(100) 2 . . . ? Cd1 S1 C23 N3 114(75) . . . . ? Cd1 N4 C24 S2 149(15) 2_545 . . . ? Cd1 S2 C24 N4 -141(16) . . . . ? Cd1 N5 C25 S3 166(17) 2_545 . . . ? Cd1 S3 C25 N5 155(17) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.400 _refine_diff_density_min -0.410 _refine_diff_density_rms 0.073 data_3-SCN _database_code_depnum_ccdc_archive 'CCDC 726094' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 Cd N5 S3' _chemical_formula_weight 582.08 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.287(3) _cell_length_b 10.751(2) _cell_length_c 34.037(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5228.2(18) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 678 _cell_measurement_theta_min 0.1 _cell_measurement_theta_max 0.2 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2368 _exptl_absorpt_coefficient_mu 1.095 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6105 _exptl_absorpt_correction_T_max 0.8108 _exptl_absorpt_process_details sadads _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% multiscan _diffrn_reflns_number 32634 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 1.20 _diffrn_reflns_theta_max 28.48 _reflns_number_total 6562 _reflns_number_gt 4554 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0544P)^2^+3.7282P] 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 0.0029(2) _refine_ls_number_reflns 6562 _refine_ls_number_parameters 292 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1240 _refine_ls_wR_factor_gt 0.1036 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.102 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.001 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 C23 C 0.1169(2) 1.1842(3) 0.19919(10) 0.0376(7) Uani 1 1 d . . . C22 C 0.1821(2) 0.6368(3) 0.25238(10) 0.0402(7) Uani 1 1 d . . . C21 C 0.1744(2) 0.6451(3) 0.15059(10) 0.0408(8) Uani 1 1 d . . . C1 C 0.8910(4) 0.8046(4) 0.20077(13) 0.0678(12) Uani 1 1 d . . . H1A H 0.9364 0.8111 0.2215 0.102 Uiso 1 1 calc R . . H1B H 0.8299 0.8225 0.2110 0.102 Uiso 1 1 calc R . . H1C H 0.9059 0.8631 0.1804 0.102 Uiso 1 1 calc R . . C2 C 0.9627(3) 0.6005(4) 0.19321(12) 0.0539(10) Uani 1 1 d . . . H2 H 1.0097 0.6271 0.2102 0.065 Uiso 1 1 calc R . . C3 C 0.9670(3) 0.4840(4) 0.17779(13) 0.0551(10) Uani 1 1 d . . . H3 H 1.0161 0.4318 0.1848 0.066 Uiso 1 1 calc R . . C4 C 0.8996(3) 0.4420(4) 0.15182(12) 0.0515(9) Uani 1 1 d . . . C5 C 0.8264(3) 0.5232(4) 0.14375(13) 0.0645(11) Uani 1 1 d . . . H5 H 0.7786 0.4988 0.1269 0.077 Uiso 1 1 calc R . . C6 C 0.8244(3) 0.6388(4) 0.16049(14) 0.0630(11) Uani 1 1 d . . . H6 H 0.7746 0.6917 0.1550 0.076 Uiso 1 1 calc R . . C7 C 0.9078(3) 0.3162(4) 0.13535(13) 0.0604(11) Uani 1 1 d . . . H7 H 0.9492 0.2614 0.1474 0.072 Uiso 1 1 calc R . . C8 C 0.8608(3) 0.2758(4) 0.10491(13) 0.0613(11) Uani 1 1 d . . . H8 H 0.8192 0.3315 0.0934 0.074 Uiso 1 1 calc R . . C9 C 0.8670(3) 0.1519(4) 0.08710(13) 0.0577(10) Uani 1 1 d . . . C10 C 0.9157(3) 0.0515(4) 0.10308(12) 0.0614(11) Uani 1 1 d . . . H10 H 0.9442 0.0609 0.1274 0.074 Uiso 1 1 calc R . . C11 C 0.9230(3) -0.0610(4) 0.08413(12) 0.0619(11) Uani 1 1 d . . . H11 H 0.9556 -0.1258 0.0959 0.074 Uiso 1 1 calc R . . C12 C 0.8817(3) -0.0791(4) 0.04715(12) 0.0602(11) Uani 1 1 d . . . C13 C 0.8303(4) 0.0198(5) 0.03212(14) 0.0754(14) Uani 1 1 d . . . H13 H 0.7994 0.0105 0.0083 0.090 Uiso 1 1 calc R . . C14 C 0.8244(4) 0.1307(5) 0.05167(14) 0.0717(13) Uani 1 1 d . . . H14 H 0.7899 0.1947 0.0404 0.086 Uiso 1 1 calc R . . C18 C 0.8444(4) -0.2078(6) -0.01170(16) 0.0902(16) Uani 1 1 d . . . H18A H 0.8362 -0.2961 -0.0165 0.108 Uiso 1 1 calc R . . H18B H 0.7832 -0.1687 -0.0119 0.108 Uiso 1 1 calc R . . C19 C 0.9019(5) -0.1546(8) -0.0417(2) 0.125(3) Uani 1 1 d . . . H19A H 0.9640 -0.1910 -0.0411 0.150 Uiso 1 1 calc R . . H19B H 0.9075 -0.0655 -0.0379 0.150 Uiso 1 1 calc R . . C20 C 0.8509(5) -0.1847(11) -0.08311(18) 0.192(5) Uani 1 1 d . . . H20A H 0.8208 -0.2645 -0.0816 0.289 Uiso 1 1 calc R . . H20B H 0.8966 -0.1857 -0.1038 0.289 Uiso 1 1 calc R . . H20C H 0.8049 -0.1218 -0.0885 0.289 Uiso 1 1 calc R . . Cd1 Cd 0.220720(17) 0.91027(2) 0.199069(8) 0.04132(10) Uani 1 1 d . . . N5 N 0.1544(2) 1.2789(3) 0.19802(9) 0.0494(8) Uani 1 1 d . . . N4 N 0.2113(3) 0.5377(3) 0.24786(13) 0.0660(10) Uani 1 1 d . . . N3 N 0.2051(2) 0.5478(3) 0.15682(11) 0.0555(8) Uani 1 1 d . . . N1 N 0.8924(2) 0.6777(3) 0.18457(10) 0.0494(7) Uani 1 1 d . . . N2 N 0.8902(4) -0.1884(4) 0.02721(12) 0.0849(14) Uani 1 1 d . . . S3 S 0.06242(7) 1.04980(8) 0.20148(3) 0.0494(2) Uani 1 1 d . . . S2 S 0.14039(7) 0.77646(8) 0.26011(3) 0.0493(2) Uani 1 1 d . . . S1 S 0.12929(8) 0.78298(9) 0.14218(3) 0.0538(3) Uani 1 1 d . . . C15 C 0.9329(6) -0.3112(9) 0.0463(2) 0.149(4) Uani 1 1 d D . . H15A H 0.9237 -0.3109 0.0745 0.179 Uiso 1 1 calc R . . H15B H 0.9030 -0.3846 0.0355 0.179 Uiso 1 1 calc R . . C16 C 1.0250(7) -0.3103(8) 0.0376(2) 0.165(4) Uani 1 1 d D . . H16A H 1.0568 -0.2407 0.0498 0.198 Uiso 1 1 calc R . . H16B H 1.0354 -0.3076 0.0094 0.198 Uiso 1 1 calc R . . C17 C 1.0598(6) -0.4475(6) 0.0569(2) 0.122(2) Uani 1 1 d D . . H17A H 1.0319 -0.4581 0.0823 0.183 Uiso 1 1 calc R . . H17B H 1.1268 -0.4481 0.0594 0.183 Uiso 1 1 calc R . . H17C H 1.0406 -0.5141 0.0400 0.183 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 C23 0.0327(16) 0.0293(16) 0.051(2) 0.0015(14) -0.0031(15) 0.0071(13) C22 0.0408(18) 0.0401(18) 0.0398(18) 0.0026(15) 0.0074(15) -0.0039(15) C21 0.0447(19) 0.0383(19) 0.0395(18) -0.0007(14) -0.0057(15) -0.0045(16) C1 0.067(3) 0.054(3) 0.082(3) -0.011(2) 0.014(2) -0.008(2) C2 0.042(2) 0.059(3) 0.061(2) 0.0091(19) -0.0036(18) -0.0071(19) C3 0.042(2) 0.050(2) 0.073(3) 0.011(2) -0.002(2) 0.0004(18) C4 0.049(2) 0.051(2) 0.055(2) 0.0060(18) 0.0055(18) -0.0037(18) C5 0.056(3) 0.067(3) 0.070(3) -0.008(2) -0.015(2) -0.002(2) C6 0.049(2) 0.067(3) 0.073(3) 0.004(2) -0.008(2) 0.009(2) C7 0.049(2) 0.067(3) 0.065(3) 0.009(2) -0.003(2) 0.002(2) C8 0.055(2) 0.066(3) 0.063(3) 0.010(2) 0.001(2) 0.001(2) C9 0.055(2) 0.059(3) 0.059(2) 0.002(2) 0.004(2) -0.006(2) C10 0.064(3) 0.074(3) 0.047(2) -0.002(2) -0.008(2) -0.008(2) C11 0.069(3) 0.064(3) 0.053(2) 0.000(2) -0.009(2) 0.004(2) C12 0.066(3) 0.065(3) 0.049(2) 0.000(2) -0.005(2) -0.002(2) C13 0.089(4) 0.074(3) 0.064(3) -0.001(2) -0.025(3) 0.002(3) C14 0.078(3) 0.068(3) 0.070(3) 0.006(2) -0.016(3) 0.006(3) C18 0.097(4) 0.094(4) 0.080(4) 0.003(3) 0.006(3) -0.002(3) C19 0.079(4) 0.170(7) 0.126(6) -0.014(5) 0.026(4) -0.022(5) C20 0.102(5) 0.426(16) 0.050(3) 0.023(6) -0.016(3) 0.007(8) Cd1 0.04140(16) 0.02428(14) 0.05827(18) 0.00003(11) -0.00277(12) 0.00021(10) N5 0.0438(17) 0.0290(15) 0.075(2) 0.0005(14) -0.0021(15) 0.0009(13) N4 0.072(2) 0.0270(16) 0.100(3) 0.0049(18) 0.022(2) 0.0088(16) N3 0.058(2) 0.0382(17) 0.070(2) 0.0027(16) -0.0082(17) -0.0001(16) N1 0.0442(17) 0.0501(19) 0.0538(18) 0.0030(15) 0.0098(15) -0.0046(15) N2 0.133(4) 0.062(3) 0.060(2) -0.009(2) -0.032(3) 0.017(3) S3 0.0388(5) 0.0288(4) 0.0806(7) -0.0008(4) -0.0021(5) -0.0023(4) S2 0.0555(6) 0.0307(4) 0.0617(6) -0.0031(4) 0.0118(5) 0.0032(4) S1 0.0640(6) 0.0367(5) 0.0607(6) -0.0036(4) -0.0178(5) 0.0094(4) C15 0.139(7) 0.201(10) 0.107(5) -0.083(6) 0.026(5) -0.069(7) C16 0.215(10) 0.194(9) 0.085(5) -0.049(6) 0.043(6) -0.107(8) C17 0.143(6) 0.104(5) 0.120(5) -0.014(4) -0.035(5) 0.039(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 C23 N5 1.151(4) . ? C23 S3 1.643(3) . ? C22 N4 1.154(5) . ? C22 S2 1.637(4) . ? C21 N3 1.154(5) . ? C21 S1 1.641(4) . ? C1 N1 1.472(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N1 1.335(5) . ? C2 C3 1.359(6) . ? C2 H2 0.9300 . ? C3 C4 1.384(6) . ? C3 H3 0.9300 . ? C4 C5 1.389(6) . ? C4 C7 1.469(6) . ? C5 C6 1.368(6) . ? C5 H5 0.9300 . ? C6 N1 1.338(5) . ? C6 H6 0.9300 . ? C7 C8 1.309(6) . ? C7 H7 0.9300 . ? C8 C9 1.466(6) . ? C8 H8 0.9300 . ? C9 C14 1.370(6) . ? C9 C10 1.395(6) . ? C10 C11 1.374(6) . ? C10 H10 0.9300 . ? C11 C12 1.404(6) . ? C11 H11 0.9300 . ? C12 N2 1.363(6) . ? C12 C13 1.390(6) . ? C13 C14 1.368(7) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C18 C19 1.428(8) . ? C18 N2 1.492(7) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.620(9) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? Cd1 N5 2.276(3) 8_655 ? Cd1 N3 2.319(3) 8_665 ? Cd1 N4 2.362(4) 8_665 ? Cd1 S1 2.7070(11) . ? Cd1 S3 2.7152(11) . ? Cd1 S2 2.7756(10) . ? N5 Cd1 2.276(3) 8_665 ? N4 Cd1 2.362(4) 8_655 ? N3 Cd1 2.319(3) 8_655 ? N2 C15 1.592(10) . ? C15 C16 1.350(10) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.690(10) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 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 N5 C23 S3 179.1(4) . . ? N4 C22 S2 178.4(4) . . ? N3 C21 S1 179.1(4) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 121.4(4) . . ? N1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C2 C3 C4 121.1(4) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C5 116.4(4) . . ? C3 C4 C7 119.3(4) . . ? C5 C4 C7 124.3(4) . . ? C6 C5 C4 120.3(4) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? N1 C6 C5 121.6(4) . . ? N1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C8 C7 C4 124.5(4) . . ? C8 C7 H7 117.7 . . ? C4 C7 H7 117.7 . . ? C7 C8 C9 126.7(4) . . ? C7 C8 H8 116.6 . . ? C9 C8 H8 116.6 . . ? C14 C9 C10 115.8(4) . . ? C14 C9 C8 119.2(4) . . ? C10 C9 C8 124.9(4) . . ? C11 C10 C9 122.4(4) . . ? C11 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? C10 C11 C12 120.7(4) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? N2 C12 C13 121.6(4) . . ? N2 C12 C11 121.9(4) . . ? C13 C12 C11 116.5(4) . . ? C14 C13 C12 121.4(4) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C9 123.1(5) . . ? C13 C14 H14 118.5 . . ? C9 C14 H14 118.5 . . ? C19 C18 N2 109.1(5) . . ? C19 C18 H18A 109.9 . . ? N2 C18 H18A 109.9 . . ? C19 C18 H18B 109.9 . . ? N2 C18 H18B 109.9 . . ? H18A C18 H18B 108.3 . . ? C18 C19 C20 106.5(6) . . ? C18 C19 H19A 110.4 . . ? C20 C19 H19A 110.4 . . ? C18 C19 H19B 110.4 . . ? C20 C19 H19B 110.4 . . ? H19A C19 H19B 108.6 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N5 Cd1 N3 91.59(12) 8_655 8_665 ? N5 Cd1 N4 92.79(12) 8_655 8_665 ? N3 Cd1 N4 83.01(14) 8_665 8_665 ? N5 Cd1 S1 93.05(8) 8_655 . ? N3 Cd1 S1 95.69(10) 8_665 . ? N4 Cd1 S1 174.04(9) 8_665 . ? N5 Cd1 S3 175.12(8) 8_655 . ? N3 Cd1 S3 92.69(9) 8_665 . ? N4 Cd1 S3 90.04(9) 8_665 . ? S1 Cd1 S3 84.20(3) . . ? N5 Cd1 S2 90.82(8) 8_655 . ? N3 Cd1 S2 169.64(9) 8_665 . ? N4 Cd1 S2 86.81(10) 8_665 . ? S1 Cd1 S2 94.24(4) . . ? S3 Cd1 S2 85.37(3) . . ? C23 N5 Cd1 155.9(3) . 8_665 ? C22 N4 Cd1 141.0(3) . 8_655 ? C21 N3 Cd1 149.9(3) . 8_655 ? C2 N1 C6 119.1(4) . . ? C2 N1 C1 120.2(4) . . ? C6 N1 C1 120.6(4) . . ? C12 N2 C18 121.6(4) . . ? C12 N2 C15 123.1(4) . . ? C18 N2 C15 114.5(4) . . ? C23 S3 Cd1 95.15(12) . . ? C22 S2 Cd1 101.79(12) . . ? C21 S1 Cd1 98.17(12) . . ? C16 C15 N2 106.1(8) . . ? C16 C15 H15A 110.5 . . ? N2 C15 H15A 110.5 . . ? C16 C15 H15B 110.5 . . ? N2 C15 H15B 110.5 . . ? H15A C15 H15B 108.7 . . ? C15 C16 C17 101.2(7) . . ? C15 C16 H16A 111.5 . . ? C17 C16 H16A 111.5 . . ? C15 C16 H16B 111.5 . . ? C17 C16 H16B 111.5 . . ? H16A C16 H16B 109.3 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 N1 C2 C3 C4 1.4(6) . . . . ? C2 C3 C4 C5 -2.3(6) . . . . ? C2 C3 C4 C7 179.0(4) . . . . ? C3 C4 C5 C6 1.3(6) . . . . ? C7 C4 C5 C6 179.9(4) . . . . ? C4 C5 C6 N1 0.7(7) . . . . ? C3 C4 C7 C8 -165.0(4) . . . . ? C5 C4 C7 C8 16.4(7) . . . . ? C4 C7 C8 C9 179.4(4) . . . . ? C7 C8 C9 C14 -169.6(5) . . . . ? C7 C8 C9 C10 8.8(7) . . . . ? C14 C9 C10 C11 1.7(7) . . . . ? C8 C9 C10 C11 -176.7(4) . . . . ? C9 C10 C11 C12 0.6(7) . . . . ? C10 C11 C12 N2 178.0(5) . . . . ? C10 C11 C12 C13 -2.9(7) . . . . ? N2 C12 C13 C14 -177.9(5) . . . . ? C11 C12 C13 C14 3.0(8) . . . . ? C12 C13 C14 C9 -0.7(8) . . . . ? C10 C9 C14 C13 -1.7(7) . . . . ? C8 C9 C14 C13 176.9(5) . . . . ? N2 C18 C19 C20 177.3(6) . . . . ? S3 C23 N5 Cd1 121(27) . . . 8_665 ? S2 C22 N4 Cd1 -174(100) . . . 8_655 ? S1 C21 N3 Cd1 -76(26) . . . 8_655 ? C3 C2 N1 C6 0.6(6) . . . . ? C3 C2 N1 C1 -178.1(4) . . . . ? C5 C6 N1 C2 -1.7(6) . . . . ? C5 C6 N1 C1 177.1(4) . . . . ? C13 C12 N2 C18 -0.3(8) . . . . ? C11 C12 N2 C18 178.7(5) . . . . ? C13 C12 N2 C15 -169.1(6) . . . . ? C11 C12 N2 C15 10.0(8) . . . . ? C19 C18 N2 C12 82.2(7) . . . . ? C19 C18 N2 C15 -108.2(7) . . . . ? N5 C23 S3 Cd1 -130(28) . . . . ? N5 Cd1 S3 C23 173.2(10) 8_655 . . . ? N3 Cd1 S3 C23 -35.41(15) 8_665 . . . ? N4 Cd1 S3 C23 47.59(15) 8_665 . . . ? S1 Cd1 S3 C23 -130.87(12) . . . . ? S2 Cd1 S3 C23 134.39(12) . . . . ? N4 C22 S2 Cd1 154(13) . . . . ? N5 Cd1 S2 C22 -28.48(16) 8_655 . . . ? N3 Cd1 S2 C22 -131.9(5) 8_665 . . . ? N4 Cd1 S2 C22 -121.23(16) 8_665 . . . ? S1 Cd1 S2 C22 64.64(14) . . . . ? S3 Cd1 S2 C22 148.46(14) . . . . ? N3 C21 S1 Cd1 96(26) . . . . ? N5 Cd1 S1 C21 27.94(15) 8_655 . . . ? N3 Cd1 S1 C21 119.85(16) 8_665 . . . ? N4 Cd1 S1 C21 -163.0(10) 8_665 . . . ? S3 Cd1 S1 C21 -148.01(14) . . . . ? S2 Cd1 S1 C21 -63.11(14) . . . . ? C12 N2 C15 C16 -92.8(7) . . . . ? C18 N2 C15 C16 97.7(6) . . . . ? N2 C15 C16 C17 -176.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.112 _refine_diff_density_min -0.773 _refine_diff_density_rms 0.250