# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 #TrackingRef '1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 Cd N6 S4' _chemical_formula_weight 528.96 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)/c 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 5.8652(12) _cell_length_b 11.593(2) _cell_length_c 15.295(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.44(3) _cell_angle_gamma 90.00 _cell_volume 1028.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 1.481 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.837 _exptl_absorpt_correction_T_max 0.862 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 9609 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2326 _reflns_number_gt 2162 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMAR' _computing_cell_refinement 'Bruker SMAR' _computing_data_reduction 'Bruker SMAR' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0185P)^2^+0.3408P] 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 SHELXL _refine_ls_extinction_coef 0.0305(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2326 _refine_ls_number_parameters 143 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0222 _refine_ls_R_factor_gt 0.0206 _refine_ls_wR_factor_ref 0.0495 _refine_ls_wR_factor_gt 0.0488 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.140 _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 0.0000 0.5000 0.5000 0.03335(8) Uani 1 2 d S . . S1 S 0.11766(9) 0.25413(5) 0.77346(3) 0.04924(14) Uani 1 1 d . . . S2 S 0.26978(7) 0.67860(4) 0.57475(3) 0.04027(12) Uani 1 1 d . . . N1 N 0.0255(4) 0.40777(19) 0.63366(13) 0.0683(6) Uani 1 1 d U . . N2 N 0.6918(3) 0.60320(16) 0.53315(14) 0.0568(5) Uani 1 1 d . . . N3 N 0.6260(3) 0.38839(18) 0.19981(13) 0.0559(5) Uani 1 1 d . . . H3 H 0.735(6) 0.365(3) 0.227(2) 0.080 Uiso 1 1 d . . . C1 C 0.0640(3) 0.34301(17) 0.69059(11) 0.0415(4) Uani 1 1 d U . . C2 C 0.5170(3) 0.63282(15) 0.55012(12) 0.0362(4) Uani 1 1 d . . . C3 C 0.0471(4) 0.52023(18) 0.03869(15) 0.0474(4) Uani 1 1 d . . . H3A H -0.032(5) 0.588(3) 0.0635(18) 0.080 Uiso 1 1 d . . . C4 C 0.5656(5) 0.3394(3) 0.12194(17) 0.0682(7) Uani 1 1 d . . . H4 H 0.645(6) 0.283(3) 0.1091(19) 0.080 Uiso 1 1 d . . . C5 C 0.3798(5) 0.3790(2) 0.06682(15) 0.0628(6) Uani 1 1 d . . . H5 H 0.330(5) 0.341(3) 0.009(2) 0.080 Uiso 1 1 d . . . C6 C 0.2537(3) 0.47126(17) 0.09176(13) 0.0426(4) Uani 1 1 d . . . C7 C 0.3264(4) 0.52092(19) 0.17367(15) 0.0508(5) Uani 1 1 d . . . H7 H 0.242(5) 0.582(3) 0.1938(19) 0.080 Uiso 1 1 d . . . C8 C 0.5112(5) 0.4766(2) 0.22713(16) 0.0565(6) Uani 1 1 d . . . H8 H 0.553(6) 0.505(2) 0.282(2) 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 Cd1 0.02526(10) 0.04277(12) 0.03232(11) 0.00543(6) 0.00517(6) 0.00439(6) S1 0.0447(3) 0.0554(3) 0.0468(3) 0.0145(2) 0.0040(2) 0.0026(2) S2 0.0302(2) 0.0436(2) 0.0477(2) -0.00761(19) 0.00797(17) 0.00457(17) N1 0.0795(14) 0.0760(13) 0.0453(10) 0.0191(9) -0.0044(9) -0.0160(11) N2 0.0315(8) 0.0528(10) 0.0875(14) -0.0200(9) 0.0129(8) -0.0010(7) N3 0.0406(9) 0.0638(12) 0.0579(11) 0.0167(9) -0.0107(8) 0.0028(8) C1 0.0375(9) 0.0514(10) 0.0348(8) 0.0019(7) 0.0028(7) -0.0074(8) C2 0.0298(8) 0.0343(8) 0.0442(9) -0.0062(7) 0.0043(7) -0.0025(6) C3 0.0477(11) 0.0427(11) 0.0492(11) -0.0017(8) -0.0021(9) 0.0051(8) C4 0.0690(16) 0.0728(16) 0.0609(14) 0.0004(12) 0.0032(12) 0.0326(13) C5 0.0730(15) 0.0654(14) 0.0458(11) -0.0079(10) -0.0048(10) 0.0219(12) C6 0.0405(9) 0.0414(9) 0.0434(10) 0.0050(7) -0.0026(8) -0.0003(8) C7 0.0575(13) 0.0416(10) 0.0504(11) -0.0025(8) -0.0021(10) 0.0026(9) C8 0.0639(14) 0.0517(12) 0.0477(11) 0.0026(9) -0.0130(10) -0.0091(10) _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 N2 2.2859(17) 3_666 ? Cd1 N2 2.2859(17) 1_455 ? Cd1 N1 2.2925(18) . ? Cd1 N1 2.2925(18) 3_566 ? Cd1 S2 2.7507(7) . ? Cd1 S2 2.7507(7) 3_566 ? S1 C1 1.6279(19) . ? S2 C2 1.6389(17) . ? N1 C1 1.147(3) . ? N2 C2 1.146(2) . ? N2 Cd1 2.2859(17) 1_655 ? N3 C4 1.320(3) . ? N3 C8 1.325(3) . ? N3 H3 0.76(3) . ? C3 C3 1.317(4) 3_565 ? C3 C6 1.470(3) . ? C3 H3A 1.02(3) . ? C4 C5 1.356(3) . ? C4 H4 0.84(3) . ? C5 C6 1.385(3) . ? C5 H5 0.99(3) . ? C6 C7 1.388(3) . ? C7 C8 1.359(3) . ? C7 H7 0.94(3) . ? C8 H8 0.90(3) . ? 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 N2 Cd1 N2 180.00(10) 3_666 1_455 ? N2 Cd1 N1 90.20(9) 3_666 . ? N2 Cd1 N1 89.80(9) 1_455 . ? N2 Cd1 N1 89.80(9) 3_666 3_566 ? N2 Cd1 N1 90.20(9) 1_455 3_566 ? N1 Cd1 N1 180.000(1) . 3_566 ? N2 Cd1 S2 93.48(5) 3_666 . ? N2 Cd1 S2 86.52(5) 1_455 . ? N1 Cd1 S2 91.27(6) . . ? N1 Cd1 S2 88.73(6) 3_566 . ? N2 Cd1 S2 86.52(5) 3_666 3_566 ? N2 Cd1 S2 93.48(5) 1_455 3_566 ? N1 Cd1 S2 88.73(6) . 3_566 ? N1 Cd1 S2 91.27(6) 3_566 3_566 ? S2 Cd1 S2 180.0 . 3_566 ? C2 S2 Cd1 97.77(6) . . ? C1 N1 Cd1 164.2(2) . . ? C2 N2 Cd1 165.82(16) . 1_655 ? C4 N3 C8 122.3(2) . . ? C4 N3 H3 116(2) . . ? C8 N3 H3 122(2) . . ? N1 C1 S1 178.3(2) . . ? N2 C2 S2 178.51(17) . . ? C3 C3 C6 124.2(3) 3_565 . ? C3 C3 H3A 117.2(17) 3_565 . ? C6 C3 H3A 118.6(17) . . ? N3 C4 C5 120.0(2) . . ? N3 C4 H4 117(2) . . ? C5 C4 H4 123(2) . . ? C4 C5 C6 120.2(2) . . ? C4 C5 H5 120.7(17) . . ? C6 C5 H5 119.0(17) . . ? C5 C6 C7 117.59(19) . . ? C5 C6 C3 125.18(19) . . ? C7 C6 C3 117.2(2) . . ? C8 C7 C6 119.9(2) . . ? C8 C7 H7 120.0(18) . . ? C6 C7 H7 120.0(18) . . ? N3 C8 C7 119.9(2) . . ? N3 C8 H8 119(2) . . ? C7 C8 H8 121(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 N3 H3 S1 0.76(3) 2.64(3) 3.371(2) 161(3) 4_665 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.449 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 934335' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 #TrackingRef '2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 Br2 Cd N4 S2' _chemical_formula_weight 587.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 10.9674(7) _cell_length_b 18.1011(9) _cell_length_c 4.9514(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 982.96(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.985 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 566 _exptl_absorpt_coefficient_mu 5.393 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.529 _exptl_absorpt_correction_T_max 0.583 _exptl_absorpt_process_details Process-auto _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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5558 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.07 _reflns_number_total 1736 _reflns_number_gt 1627 _reflns_threshold_expression >2sigma(I) _computing_data_collection Process-auto _computing_cell_refinement Process-auto _computing_data_reduction Process-auto _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0234P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.005(9) _refine_ls_number_reflns 1736 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0201 _refine_ls_R_factor_gt 0.0180 _refine_ls_wR_factor_ref 0.0436 _refine_ls_wR_factor_gt 0.0431 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 0.0000 0.0000 0.26440(7) 0.04157(10) Uani 1 2 d S . . Br1 Br -0.10870(3) -0.101058(18) 0.54683(7) 0.04705(11) Uani 1 1 d . . . S1 S -0.17452(9) 0.06094(4) 0.00633(17) 0.0460(2) Uani 1 1 d . . . N1 N 0.0686(3) -0.24217(14) -0.1820(5) 0.0453(7) Uani 1 1 d . . . H1A H 0.0758 -0.2040 -0.2844 0.054 Uiso 1 1 calc R . . N2 N -0.2260(3) 0.17419(19) 0.3782(6) 0.0636(9) Uani 1 1 d . . . C1 C 0.1484(3) -0.29743(17) -0.2060(7) 0.0442(8) Uani 1 1 d . . . H1B H 0.2115 -0.2943 -0.3309 0.053 Uiso 1 1 calc R . . C2 C 0.1371(3) -0.35889(16) -0.0457(7) 0.0437(8) Uani 1 1 d . . . H2A H 0.1928 -0.3974 -0.0621 0.052 Uiso 1 1 calc R . . C3 C 0.0434(3) -0.36383(15) 0.1399(6) 0.0348(7) Uani 1 1 d . . . C4 C -0.0375(3) -0.30513(17) 0.1594(6) 0.0447(8) Uani 1 1 d . . . H4A H -0.1017 -0.3069 0.2819 0.054 Uiso 1 1 calc R . . C5 C -0.0221(4) -0.24472(17) -0.0027(7) 0.0516(9) Uani 1 1 d . . . H5A H -0.0755 -0.2050 0.0121 0.062 Uiso 1 1 calc R . . C6 C 0.0277(3) -0.43195(16) 0.3088(6) 0.0450(9) Uani 1 1 d . . . H6A H -0.0385 -0.4243 0.4357 0.054 Uiso 1 1 calc R . . H6B H 0.1016 -0.4406 0.4117 0.054 Uiso 1 1 calc R . . C7 C 0.0000 -0.5000 0.1359(9) 0.0377(10) Uani 1 2 d S . . C8 C -0.2042(3) 0.12676(17) 0.2328(7) 0.0419(7) Uani 1 1 d . . . H01 H -0.062(3) -0.493(2) 0.012(6) 0.055(10) 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 Cd1 0.03480(18) 0.02997(15) 0.0600(2) 0.000 0.000 -0.00070(14) Br1 0.04249(19) 0.04063(17) 0.0580(2) 0.01029(16) -0.00157(17) -0.00619(15) S1 0.0459(5) 0.0437(4) 0.0484(5) -0.0034(4) -0.0054(4) 0.0039(4) N1 0.0571(19) 0.0344(14) 0.0443(15) 0.0048(12) -0.0013(14) -0.0020(14) N2 0.067(2) 0.0586(19) 0.0650(19) -0.0125(17) 0.0011(19) 0.0101(17) C1 0.042(2) 0.0436(18) 0.0464(19) -0.0038(16) 0.0034(16) -0.0043(15) C2 0.043(2) 0.0341(17) 0.0535(19) -0.0036(16) 0.0008(17) 0.0021(14) C3 0.0423(19) 0.0271(15) 0.0350(15) -0.0048(12) -0.0047(14) -0.0062(14) C4 0.043(2) 0.0433(18) 0.0479(18) 0.0006(16) 0.0077(15) 0.0046(15) C5 0.058(2) 0.0391(17) 0.058(2) 0.0011(16) 0.006(2) 0.0140(16) C6 0.060(3) 0.0321(16) 0.0425(17) 0.0003(13) -0.0013(16) -0.0033(15) C7 0.041(3) 0.031(2) 0.041(2) 0.000 0.000 -0.002(2) C8 0.0369(18) 0.0425(17) 0.0464(18) 0.0073(17) 0.0022(17) 0.0003(14) _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 S1 2.5521(9) . ? Cd1 S1 2.5521(9) 2 ? Cd1 Br1 2.5929(4) 2 ? Cd1 Br1 2.5929(4) . ? S1 C8 1.668(4) . ? N1 C5 1.334(4) . ? N1 C1 1.335(4) . ? N2 C8 1.146(4) . ? C1 C2 1.372(4) . ? C2 C3 1.382(5) . ? C3 C4 1.388(4) . ? C3 C6 1.500(4) . ? C4 C5 1.367(4) . ? C6 C7 1.531(4) . ? C7 C6 1.531(4) 2_545 ? 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 S1 Cd1 S1 119.91(4) . 2 ? S1 Cd1 Br1 108.06(2) . 2 ? S1 Cd1 Br1 103.31(2) 2 2 ? S1 Cd1 Br1 103.31(2) . . ? S1 Cd1 Br1 108.06(2) 2 . ? Br1 Cd1 Br1 114.72(2) 2 . ? C8 S1 Cd1 96.81(12) . . ? C5 N1 C1 121.5(3) . . ? N1 C1 C2 119.8(3) . . ? C1 C2 C3 120.3(3) . . ? C2 C3 C4 118.2(3) . . ? C2 C3 C6 120.7(3) . . ? C4 C3 C6 121.1(3) . . ? C5 C4 C3 119.5(3) . . ? N1 C5 C4 120.7(3) . . ? C3 C6 C7 111.9(3) . . ? C6 C7 C6 112.0(4) . 2_545 ? N2 C8 S1 176.7(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.304 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 934336' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 #TrackingRef '3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H27 Br2 Cd3 N8 S6' _chemical_formula_weight 1056.87 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.015(2) _cell_length_b 5.9167(3) _cell_length_c 21.7640(18) _cell_angle_alpha 90.00 _cell_angle_beta 113.306(8) _cell_angle_gamma 90.00 _cell_volume 3313.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.119 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2028 _exptl_absorpt_coefficient_mu 4.723 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.573 _exptl_absorpt_correction_T_max 0.595 _exptl_absorpt_process_details Process-auto _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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8841 _diffrn_reflns_av_R_equivalents 0.0669 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2898 _reflns_number_gt 2446 _reflns_threshold_expression >2sigma(I) _computing_data_collection Process-auto _computing_cell_refinement Process-auto _computing_data_reduction Process-auto _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0327P)^2^+12.9771P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2898 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0858 _refine_ls_wR_factor_gt 0.0823 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.5000 0.5000 0.5000 0.03772(15) Uani 1 2 d S . . Cd2 Cd 0.651107(15) 0.72825(6) 0.55930(2) 0.04087(14) Uani 1 1 d . . . Br1 Br 0.73189(2) 0.66056(10) 0.67503(3) 0.05551(18) Uani 1 1 d . . . S1 S 0.41247(5) 0.53330(19) 0.38716(6) 0.0365(3) Uani 1 1 d . . . S2 S 0.55643(5) 0.75149(18) 0.44376(6) 0.0364(3) Uani 1 1 d . . . S3 S 0.70416(6) 0.9788(2) 0.50442(8) 0.0504(4) Uani 1 1 d . . . N1 N 0.37894(17) 0.9698(7) 0.4019(2) 0.0414(10) Uani 1 1 d . . . N2 N 0.51950(17) 1.1855(7) 0.4544(2) 0.0388(10) Uani 1 1 d . . . N3 N 0.66281(19) 1.4051(7) 0.5111(2) 0.0481(11) Uani 1 1 d . . . N4 N 0.2875(2) 0.3328(9) 0.1745(3) 0.0793(17) Uani 1 1 d . . . H4A H 0.2726 0.4160 0.1377 0.080 Uiso 1 1 calc . . . H4B H 0.2924 0.4169 0.2104 0.080 Uiso 1 1 calc . . . H4C H 0.2671 0.2162 0.1732 0.080 Uiso 1 1 calc . . . C1 C 0.39283(18) 0.7906(8) 0.3964(2) 0.0328(10) Uani 1 1 d . . . C2 C 0.53451(18) 1.0063(7) 0.4504(2) 0.0313(10) Uani 1 1 d . . . C3 C 0.67941(19) 1.2289(8) 0.5085(2) 0.0359(11) Uani 1 1 d . . . C4 C 0.4522(3) 0.2041(14) 0.2432(4) 0.079(2) Uani 1 1 d . . . H4CA H 0.4602 0.3017 0.2824 0.095 Uiso 1 1 calc R . . C5 C 0.4151(3) 0.0200(13) 0.2444(5) 0.103(3) Uani 1 1 d . . . H5A H 0.4093 -0.0827 0.2074 0.124 Uiso 1 1 calc R . . H5B H 0.4308 -0.0654 0.2856 0.124 Uiso 1 1 calc R . . C6 C 0.3646(3) 0.1102(11) 0.2395(3) 0.071(2) Uani 1 1 d . . . H6A H 0.3698 0.2032 0.2784 0.085 Uiso 1 1 calc R . . H6B H 0.3420 -0.0142 0.2393 0.085 Uiso 1 1 calc R . . C7 C 0.3393(2) 0.2465(9) 0.1781(3) 0.0480(13) Uani 1 1 d . . . H7A H 0.3328 0.1474 0.1396 0.058 Uiso 1 1 calc R . . C8 C 0.3745(3) 0.4356(11) 0.1750(4) 0.0659(17) Uani 1 1 d . . . H8A H 0.3577 0.5184 0.1335 0.079 Uiso 1 1 calc R . . H8B H 0.3803 0.5394 0.2118 0.079 Uiso 1 1 calc R . . C9 C 0.4257(3) 0.3454(15) 0.1790(4) 0.088(2) Uani 1 1 d . . . H9A H 0.4481 0.4701 0.1788 0.105 Uiso 1 1 calc R . . H9B H 0.4202 0.2520 0.1401 0.105 Uiso 1 1 calc R . . C10 C 0.5000 0.072(3) 0.2500 0.113(4) Uani 1 2 d S . . 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 0.0384(3) 0.0222(3) 0.0507(3) -0.0044(2) 0.0157(2) 0.00510(19) Cd2 0.0432(2) 0.0239(2) 0.0539(3) -0.00127(15) 0.01752(18) 0.00583(15) Br1 0.0451(3) 0.0509(3) 0.0598(4) 0.0046(3) 0.0093(3) 0.0090(3) S1 0.0407(7) 0.0257(6) 0.0414(7) -0.0048(5) 0.0145(6) 0.0045(5) S2 0.0450(7) 0.0223(6) 0.0445(7) -0.0032(5) 0.0206(6) 0.0063(5) S3 0.0588(9) 0.0292(7) 0.0776(10) 0.0047(6) 0.0425(8) 0.0087(6) N1 0.049(3) 0.028(2) 0.046(3) 0.0031(18) 0.018(2) 0.0076(19) N2 0.046(2) 0.027(2) 0.045(2) -0.0002(18) 0.020(2) 0.0066(18) N3 0.061(3) 0.026(2) 0.067(3) 0.002(2) 0.035(2) 0.008(2) N4 0.075(4) 0.053(3) 0.114(5) -0.001(3) 0.041(4) -0.004(3) C1 0.032(2) 0.030(2) 0.034(3) 0.0033(19) 0.011(2) 0.004(2) C2 0.038(3) 0.024(2) 0.035(3) 0.0006(18) 0.017(2) 0.0021(19) C3 0.038(3) 0.030(3) 0.042(3) 0.000(2) 0.018(2) -0.001(2) C4 0.058(4) 0.092(5) 0.083(5) -0.014(4) 0.023(4) -0.002(4) C5 0.058(5) 0.079(5) 0.130(8) 0.042(5) -0.008(5) -0.006(4) C6 0.067(4) 0.064(4) 0.061(4) 0.008(3) 0.002(3) -0.029(3) C7 0.050(3) 0.043(3) 0.049(3) -0.004(2) 0.017(3) -0.003(2) C8 0.072(4) 0.054(4) 0.074(4) 0.018(3) 0.032(4) -0.003(3) C9 0.063(5) 0.101(6) 0.111(7) 0.008(5) 0.048(5) -0.015(4) C10 0.070(8) 0.128(11) 0.147(12) 0.000 0.049(8) 0.000 _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 N2 2.275(4) 1_545 ? Cd1 N2 2.275(4) 5_676 ? Cd1 S1 2.7052(13) . ? Cd1 S1 2.7052(13) 5_666 ? Cd1 S2 2.7826(13) . ? Cd1 S2 2.7826(13) 5_666 ? Cd2 N3 2.267(4) 1_545 ? Cd2 N1 2.275(4) 5_676 ? Cd2 Br1 2.6676(8) . ? Cd2 S3 2.6906(14) . ? Cd2 S2 2.8461(14) . ? Cd2 S1 2.9268(14) 5_666 ? S1 C1 1.658(5) . ? S1 Cd2 2.9268(14) 5_666 ? S2 C2 1.656(4) . ? S3 C3 1.651(5) . ? N1 C1 1.152(6) . ? N1 Cd2 2.275(4) 5_676 ? N2 C2 1.156(6) . ? N2 Cd1 2.275(4) 1_565 ? N3 C3 1.152(6) . ? N3 Cd2 2.267(4) 1_565 ? N4 C7 1.511(8) . ? C4 C10 1.506(10) . ? C4 C5 1.513(10) . ? C4 C9 1.544(11) . ? C5 C6 1.476(11) . ? C6 C7 1.479(8) . ? C7 C8 1.509(8) . ? C8 C9 1.501(10) . ? C10 C4 1.506(11) 2_655 ? 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 N2 Cd1 N2 180.00(19) 1_545 5_676 ? N2 Cd1 S1 87.20(11) 1_545 . ? N2 Cd1 S1 92.80(11) 5_676 . ? N2 Cd1 S1 92.80(11) 1_545 5_666 ? N2 Cd1 S1 87.20(11) 5_676 5_666 ? S1 Cd1 S1 180.00(5) . 5_666 ? N2 Cd1 S2 88.22(11) 1_545 . ? N2 Cd1 S2 91.78(11) 5_676 . ? S1 Cd1 S2 91.74(4) . . ? S1 Cd1 S2 88.26(4) 5_666 . ? N2 Cd1 S2 91.78(11) 1_545 5_666 ? N2 Cd1 S2 88.22(11) 5_676 5_666 ? S1 Cd1 S2 88.26(4) . 5_666 ? S1 Cd1 S2 91.74(4) 5_666 5_666 ? S2 Cd1 S2 180.00(4) . 5_666 ? N3 Cd2 N1 167.65(17) 1_545 5_676 ? N3 Cd2 Br1 94.97(12) 1_545 . ? N1 Cd2 Br1 93.89(11) 5_676 . ? N3 Cd2 S3 93.02(12) 1_545 . ? N1 Cd2 S3 94.73(11) 5_676 . ? Br1 Cd2 S3 95.20(4) . . ? N3 Cd2 S2 83.48(13) 1_545 . ? N1 Cd2 S2 86.42(11) 5_676 . ? Br1 Cd2 S2 170.92(3) . . ? S3 Cd2 S2 93.82(5) . . ? N3 Cd2 S1 87.74(12) 1_545 5_666 ? N1 Cd2 S1 83.96(11) 5_676 5_666 ? Br1 Cd2 S1 88.13(3) . 5_666 ? S3 Cd2 S1 176.51(4) . 5_666 ? S2 Cd2 S1 82.88(4) . 5_666 ? C1 S1 Cd1 100.48(17) . . ? C1 S1 Cd2 98.87(17) . 5_666 ? Cd1 S1 Cd2 94.35(4) . 5_666 ? C2 S2 Cd1 98.82(17) . . ? C2 S2 Cd2 102.39(17) . . ? Cd1 S2 Cd2 94.50(4) . . ? C3 S3 Cd2 98.79(18) . . ? C1 N1 Cd2 162.1(4) . 5_676 ? C2 N2 Cd1 159.9(4) . 1_565 ? C3 N3 Cd2 157.1(4) . 1_565 ? N1 C1 S1 179.1(4) . . ? N2 C2 S2 178.9(4) . . ? N3 C3 S3 178.8(5) . . ? C10 C4 C5 102.5(8) . . ? C10 C4 C9 117.3(6) . . ? C5 C4 C9 108.5(6) . . ? C6 C5 C4 112.6(7) . . ? C5 C6 C7 111.4(6) . . ? C6 C7 C8 111.0(5) . . ? C6 C7 N4 109.7(6) . . ? C8 C7 N4 112.2(5) . . ? C9 C8 C7 111.1(6) . . ? C8 C9 C4 110.5(6) . . ? C4 C10 C4 117.7(12) 2_655 . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.111 _refine_diff_density_min -0.619 _refine_diff_density_rms 0.113 _database_code_depnum_ccdc_archive 'CCDC 934337' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H26 Cd3 N12 O0 S8' _chemical_formula_weight 1028.21 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7352(4) _cell_length_b 12.2620(7) _cell_length_c 14.6609(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.067(4) _cell_angle_gamma 90.00 _cell_volume 1728.25(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.976 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1004 _exptl_absorpt_coefficient_mu 2.347 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.755 _exptl_absorpt_correction_T_max 0.791 _exptl_absorpt_process_details process-auto _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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9565 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.08 _reflns_number_total 3072 _reflns_number_gt 2832 _reflns_threshold_expression >2sigma(I) _computing_data_collection process-auto _computing_cell_refinement process-auto _computing_data_reduction process-auto _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+1.0153P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3072 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0260 _refine_ls_R_factor_gt 0.0232 _refine_ls_wR_factor_ref 0.0619 _refine_ls_wR_factor_gt 0.0590 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _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 Cd1 Cd 0.366414(18) -0.367863(15) 0.866656(12) 0.02913(8) Uani 1 1 d . . . S1 S 0.26014(7) 0.01379(5) 0.96963(5) 0.03280(16) Uani 1 1 d . . . S2 S 0.56388(9) -0.29526(6) 0.57973(6) 0.0465(2) Uani 1 1 d . . . S3 S 0.61415(9) -0.30471(7) 0.95689(7) 0.0512(2) Uani 1 1 d . . . S4 S 0.60771(7) -0.60301(6) 0.66329(5) 0.03585(16) Uani 1 1 d . . . N1 N 0.2827(3) -0.2023(2) 0.91187(17) 0.0386(5) Uani 1 1 d . . . N2 N 0.4157(3) -0.2887(2) 0.72850(17) 0.0407(6) Uani 1 1 d . . . N3 N 0.6863(3) -0.5150(2) 1.0206(2) 0.0493(7) Uani 1 1 d . . . N4 N 0.4572(3) -0.5206(2) 0.7961(2) 0.0459(6) Uani 1 1 d . . . N5 N 0.1282(2) -0.40341(17) 0.79608(14) 0.0269(4) Uani 1 1 d . . . N6 N -0.1147(3) -0.4401(2) 0.71260(18) 0.0384(5) Uani 1 1 d . . . C1 C 0.2721(3) -0.1140(2) 0.93606(17) 0.0281(5) Uani 1 1 d . . . C2 C 0.4747(3) -0.2938(2) 0.66673(19) 0.0310(6) Uani 1 1 d . . . C3 C 0.6571(3) -0.4280(3) 0.99498(19) 0.0372(6) Uani 1 1 d . . . C4 C 0.5190(3) -0.5525(2) 0.74110(18) 0.0304(6) Uani 1 1 d . . . C5 C 0.0921(3) -0.3267(2) 0.71786(19) 0.0346(6) Uani 1 1 d . . . H5A H 0.1543 -0.3383 0.6732 0.041 Uiso 1 1 calc R . . H5B H 0.1045 -0.2524 0.7403 0.041 Uiso 1 1 calc R . . C6 C -0.0577(3) -0.3425(3) 0.6710(2) 0.0481(8) Uani 1 1 d . . . H6A H -0.1125 -0.2786 0.6802 0.058 Uiso 1 1 calc R . . H6B H -0.0608 -0.3532 0.6052 0.058 Uiso 1 1 calc R . . C7 C 0.1173(3) -0.5164(2) 0.7606(2) 0.0350(6) Uani 1 1 d . . . H7A H 0.1329 -0.5670 0.8120 0.042 Uiso 1 1 calc R . . H7B H 0.1886 -0.5289 0.7224 0.042 Uiso 1 1 calc R . . C8 C -0.0251(3) -0.5372(2) 0.7042(3) 0.0456(7) Uani 1 1 d . . . H8A H -0.0164 -0.5492 0.6400 0.055 Uiso 1 1 calc R . . H8B H -0.0665 -0.6017 0.7270 0.055 Uiso 1 1 calc R . . C9 C 0.0259(3) -0.3897(3) 0.8602(2) 0.0390(6) Uani 1 1 d . . . H9A H 0.0274 -0.3147 0.8815 0.047 Uiso 1 1 calc R . . H9B H 0.0512 -0.4363 0.9136 0.047 Uiso 1 1 calc R . . C10 C -0.1198(3) -0.4185(3) 0.8124(2) 0.0536(9) Uani 1 1 d . . . H10A H -0.1532 -0.4827 0.8408 0.064 Uiso 1 1 calc R . . H10B H -0.1831 -0.3587 0.8183 0.064 Uiso 1 1 calc R . . H0 H -0.192(4) -0.450(3) 0.686(2) 0.047(10) Uiso 1 1 d . . . Cd2 Cd 0.5000 -0.5000 0.5000 0.03663(10) Uani 1 2 d S . . 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 0.03047(12) 0.02798(12) 0.02862(12) -0.00146(7) 0.00373(8) 0.00411(7) S1 0.0357(3) 0.0286(3) 0.0353(4) -0.0042(3) 0.0094(3) 0.0020(3) S2 0.0581(5) 0.0430(4) 0.0440(4) -0.0071(3) 0.0253(4) -0.0163(3) S3 0.0441(4) 0.0396(4) 0.0643(5) 0.0024(4) -0.0089(4) -0.0016(3) S4 0.0355(4) 0.0379(4) 0.0353(4) 0.0012(3) 0.0093(3) -0.0030(3) N1 0.0407(13) 0.0338(13) 0.0432(14) -0.0061(11) 0.0123(11) 0.0057(10) N2 0.0502(15) 0.0383(13) 0.0363(13) -0.0013(10) 0.0147(12) -0.0006(11) N3 0.0423(15) 0.0587(18) 0.0460(16) 0.0191(13) 0.0044(12) 0.0078(12) N4 0.0519(16) 0.0402(14) 0.0479(16) -0.0076(12) 0.0150(13) 0.0065(12) N5 0.0283(11) 0.0251(10) 0.0273(11) -0.0026(9) 0.0039(9) 0.0020(8) N6 0.0244(12) 0.0397(13) 0.0487(14) -0.0072(11) -0.0013(11) 0.0007(10) C1 0.0258(12) 0.0340(15) 0.0249(12) 0.0019(11) 0.0056(10) 0.0032(10) C2 0.0354(13) 0.0240(12) 0.0325(14) -0.0004(10) 0.0021(11) -0.0022(10) C3 0.0282(13) 0.0526(19) 0.0302(13) 0.0050(13) 0.0023(11) 0.0040(12) C4 0.0332(13) 0.0224(12) 0.0336(14) 0.0010(11) -0.0010(11) -0.0034(10) C5 0.0356(14) 0.0332(14) 0.0330(14) -0.0007(11) -0.0005(11) 0.0007(11) C6 0.0442(17) 0.0444(17) 0.0500(19) 0.0049(15) -0.0101(14) 0.0002(14) C7 0.0327(14) 0.0280(14) 0.0422(16) -0.0083(11) -0.0003(12) 0.0035(11) C8 0.0372(16) 0.0327(15) 0.063(2) -0.0146(14) -0.0056(14) 0.0032(12) C9 0.0363(15) 0.0482(16) 0.0334(15) -0.0079(13) 0.0083(12) 0.0032(12) C10 0.0336(16) 0.073(2) 0.057(2) -0.0161(18) 0.0161(14) -0.0054(15) Cd2 0.03191(16) 0.04777(19) 0.03120(16) -0.00019(12) 0.00804(12) -0.01127(12) _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 2.308(3) 3_647 ? Cd1 N1 2.323(2) . ? Cd1 N2 2.362(2) . ? Cd1 N4 2.377(3) . ? Cd1 N5 2.426(2) . ? Cd1 S3 2.6760(8) . ? S1 C1 1.652(3) . ? S1 Cd2 2.6450(7) 2_556 ? S2 C2 1.652(3) . ? S2 Cd2 2.7976(8) . ? S3 C3 1.643(3) . ? S4 C4 1.656(3) . ? S4 Cd2 2.7631(7) . ? N1 C1 1.149(3) . ? N2 C2 1.148(4) . ? N3 C3 1.151(4) . ? N3 Cd1 2.308(3) 3_647 ? N4 C4 1.148(4) . ? N5 C7 1.478(3) . ? N5 C5 1.482(3) . ? N5 C9 1.482(3) . ? N6 C6 1.489(4) . ? N6 C8 1.492(4) . ? N6 C10 1.495(4) . ? C5 C6 1.523(4) . ? C7 C8 1.520(4) . ? C9 C10 1.522(4) . ? Cd2 S1 2.6450(7) 4_655 ? Cd2 S1 2.6450(7) 2_546 ? Cd2 S4 2.7631(7) 3_646 ? Cd2 S2 2.7976(8) 3_646 ? 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 N1 102.23(10) 3_647 . ? N3 Cd1 N2 165.44(10) 3_647 . ? N1 Cd1 N2 90.78(9) . . ? N3 Cd1 N4 87.78(10) 3_647 . ? N1 Cd1 N4 169.86(9) . . ? N2 Cd1 N4 79.09(9) . . ? N3 Cd1 N5 83.57(9) 3_647 . ? N1 Cd1 N5 85.63(8) . . ? N2 Cd1 N5 91.02(8) . . ? N4 Cd1 N5 93.95(8) . . ? N3 Cd1 S3 96.37(7) 3_647 . ? N1 Cd1 S3 86.30(7) . . ? N2 Cd1 S3 90.92(7) . . ? N4 Cd1 S3 94.31(7) . . ? N5 Cd1 S3 171.73(5) . . ? C1 S1 Cd2 95.95(9) . 2_556 ? C2 S2 Cd2 102.90(9) . . ? C3 S3 Cd1 93.62(10) . . ? C4 S4 Cd2 104.96(9) . . ? C1 N1 Cd1 164.6(2) . . ? C2 N2 Cd1 148.1(2) . . ? C3 N3 Cd1 137.6(3) . 3_647 ? C4 N4 Cd1 147.8(2) . . ? C7 N5 C5 109.1(2) . . ? C7 N5 C9 108.2(2) . . ? C5 N5 C9 108.5(2) . . ? C7 N5 Cd1 109.21(15) . . ? C5 N5 Cd1 108.07(15) . . ? C9 N5 Cd1 113.68(16) . . ? C6 N6 C8 110.3(3) . . ? C6 N6 C10 109.3(3) . . ? C8 N6 C10 109.4(3) . . ? N1 C1 S1 178.6(3) . . ? N2 C2 S2 177.1(3) . . ? N3 C3 S3 179.1(3) . . ? N4 C4 S4 177.9(3) . . ? N5 C5 C6 111.2(2) . . ? N6 C6 C5 108.1(2) . . ? N5 C7 C8 110.9(2) . . ? N6 C8 C7 108.4(2) . . ? N5 C9 C10 110.6(2) . . ? N6 C10 C9 108.6(2) . . ? S1 Cd2 S1 180.0 4_655 2_546 ? S1 Cd2 S4 82.76(2) 4_655 . ? S1 Cd2 S4 97.24(2) 2_546 . ? S1 Cd2 S4 97.24(2) 4_655 3_646 ? S1 Cd2 S4 82.76(2) 2_546 3_646 ? S4 Cd2 S4 180.0 . 3_646 ? S1 Cd2 S2 91.60(2) 4_655 3_646 ? S1 Cd2 S2 88.40(2) 2_546 3_646 ? S4 Cd2 S2 88.90(2) . 3_646 ? S4 Cd2 S2 91.10(2) 3_646 3_646 ? S1 Cd2 S2 88.40(2) 4_655 . ? S1 Cd2 S2 91.60(2) 2_546 . ? S4 Cd2 S2 91.10(2) . . ? S4 Cd2 S2 88.90(2) 3_646 . ? S2 Cd2 S2 180.00(4) 3_646 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.522 _refine_diff_density_min -0.852 _refine_diff_density_rms 0.133 _database_code_depnum_ccdc_archive 'CCDC 937884' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4 #TrackingRef '4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H22 Cd N6 Se4' _chemical_formula_weight 702.62 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' Se Se -0.0929 2.2259 '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)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 6.3554(13) _cell_length_b 17.096(3) _cell_length_c 10.443(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.90(3) _cell_angle_gamma 90.00 _cell_volume 1110.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.102 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 7.550 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.420 _exptl_absorpt_correction_T_max 0.470 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 10881 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0661 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2626 _reflns_number_gt 2228 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMAR' _computing_cell_refinement 'Bruker SMAR' _computing_data_reduction 'Bruker SMAR' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0206P)^2^+1.1056P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2626 _refine_ls_number_parameters 132 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0375 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0642 _refine_ls_wR_factor_gt 0.0608 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 -0.89565(5) 0.7500 0.24124(3) 0.03011(10) Uani 1 2 d S . . Se1 Se -0.86054(9) 0.7500 0.49717(5) 0.05001(15) Uani 1 2 d S . . Se2 Se -0.49524(7) 0.7500 0.20537(5) 0.03905(13) Uani 1 2 d S . . Se3 Se -1.09958(5) 0.626056(19) 0.12445(4) 0.04163(11) Uani 1 1 d . . . N1 N -0.5074(5) 0.5865(2) 0.8180(3) 0.0411(7) Uani 1 1 d . . . H0B H -0.527(5) 0.6219(19) 0.872(3) 0.030(9) Uiso 1 1 d . . . H0A H -0.447(7) 0.546(3) 0.869(4) 0.061(13) Uiso 1 1 d . . . N2 N -1.3263(10) 0.7500 0.5028(6) 0.0710(15) Uani 1 2 d S . . N3 N -0.6144(9) 0.7500 -0.0848(5) 0.0570(12) Uani 1 2 d S . . N4 N -0.7180(5) 0.55124(17) 0.0521(3) 0.0453(7) Uani 1 1 d . . . C1 C -0.3522(6) 0.6175(2) 0.7407(4) 0.0491(9) Uani 1 1 d . . . H1B H -0.2170 0.6298 0.7994 0.059 Uiso 1 1 calc R . . H1C H -0.4087 0.6654 0.6970 0.059 Uiso 1 1 calc R . . C2 C -0.3130(5) 0.5581(2) 0.6393(4) 0.0417(8) Uani 1 1 d . . . H2A H -0.2196 0.5812 0.5869 0.050 Uiso 1 1 calc R . . H2B H -0.2396 0.5130 0.6840 0.050 Uiso 1 1 calc R . . C3 C -0.5203(5) 0.53119(19) 0.5490(3) 0.0338(7) Uani 1 1 d . . . H3A H -0.5858 0.5767 0.4992 0.041 Uiso 1 1 calc R . . C4 C -0.6760(5) 0.5022(2) 0.6334(4) 0.0424(8) Uani 1 1 d . . . H4A H -0.8122 0.4887 0.5768 0.051 Uiso 1 1 calc R . . H4B H -0.6178 0.4551 0.6794 0.051 Uiso 1 1 calc R . . C5 C -0.7149(5) 0.5624(2) 0.7323(3) 0.0416(8) Uani 1 1 d . . . H5A H -0.7853 0.6078 0.6868 0.050 Uiso 1 1 calc R . . H5B H -0.8089 0.5406 0.7854 0.050 Uiso 1 1 calc R . . C6 C -1.1468(10) 0.7500 0.4985(5) 0.0486(13) Uani 1 2 d S . . C7 C -0.5742(8) 0.7500 0.0270(6) 0.0404(11) Uani 1 2 d S . . C8 C -0.8632(5) 0.58151(17) 0.0802(3) 0.0340(7) 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 0.03447(18) 0.02776(16) 0.03114(18) 0.000 0.01381(14) 0.000 Se1 0.0560(3) 0.0656(4) 0.0285(3) 0.000 0.0089(2) 0.000 Se2 0.0293(2) 0.0469(3) 0.0434(3) 0.000 0.0130(2) 0.000 Se3 0.03437(18) 0.03517(18) 0.0571(3) -0.01378(16) 0.01354(16) -0.00337(13) N1 0.0499(18) 0.0450(17) 0.0316(17) -0.0059(15) 0.0161(14) 0.0046(14) N2 0.072(4) 0.096(4) 0.052(3) 0.000 0.028(3) 0.000 N3 0.078(3) 0.050(3) 0.048(3) 0.000 0.026(3) 0.000 N4 0.0491(17) 0.0438(16) 0.0456(19) -0.0067(15) 0.0161(15) 0.0085(14) C1 0.054(2) 0.056(2) 0.041(2) -0.0105(18) 0.0169(18) -0.0114(17) C2 0.0404(19) 0.052(2) 0.036(2) -0.0045(16) 0.0164(15) -0.0032(15) C3 0.0370(17) 0.0400(16) 0.0260(16) 0.0042(14) 0.0104(13) 0.0055(14) C4 0.0393(18) 0.053(2) 0.038(2) -0.0079(16) 0.0154(16) -0.0037(15) C5 0.0402(18) 0.051(2) 0.036(2) -0.0015(16) 0.0142(15) 0.0055(15) C6 0.066(4) 0.053(3) 0.032(3) 0.000 0.020(3) 0.000 C7 0.043(3) 0.034(2) 0.049(3) 0.000 0.021(2) 0.000 C8 0.0431(18) 0.0280(14) 0.0312(18) -0.0019(13) 0.0085(14) -0.0006(13) _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 Se1 2.6357(8) . ? Cd1 Se3 2.6467(6) . ? Cd1 Se3 2.6467(6) 4_575 ? Cd1 Se2 2.6475(8) . ? Se1 C6 1.822(6) . ? Se2 C7 1.826(6) . ? Se3 C8 1.827(3) . ? N1 C5 1.491(5) . ? N1 C1 1.495(5) . ? N2 C6 1.151(7) . ? N3 C7 1.143(7) . ? N4 C8 1.148(4) . ? C1 C2 1.525(5) . ? C2 C3 1.524(5) . ? C3 C4 1.537(4) . ? C3 C3 1.537(6) 3_466 ? C4 C5 1.514(5) . ? 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 Se1 Cd1 Se3 113.469(19) . . ? Se1 Cd1 Se3 113.469(19) . 4_575 ? Se3 Cd1 Se3 106.37(3) . 4_575 ? Se1 Cd1 Se2 105.11(4) . . ? Se3 Cd1 Se2 109.175(18) . . ? Se3 Cd1 Se2 109.175(18) 4_575 . ? C6 Se1 Cd1 97.58(17) . . ? C7 Se2 Cd1 94.26(16) . . ? C8 Se3 Cd1 95.75(10) . . ? C5 N1 C1 112.0(3) . . ? N1 C1 C2 111.0(3) . . ? C3 C2 C1 112.7(3) . . ? C2 C3 C4 108.6(3) . . ? C2 C3 C3 112.3(3) . 3_466 ? C4 C3 C3 112.0(3) . 3_466 ? C5 C4 C3 112.7(3) . . ? N1 C5 C4 110.4(3) . . ? N2 C6 Se1 178.3(5) . . ? N3 C7 Se2 177.1(5) . . ? N4 C8 Se3 177.8(3) . . ? 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 N1 H0B N3 0.86(3) 2.32(3) 3.097(4) 150(3) 1_556 N1 H0A N4 0.90(5) 2.05(5) 2.938(5) 166(4) 3_466 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.136 _refine_diff_density_min -0.783 _refine_diff_density_rms 0.104 _database_code_depnum_ccdc_archive 'CCDC 934338' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_5 #TrackingRef '5.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 Br0 Cd Cl0 N6 O2 S0 Se4' _chemical_formula_weight 706.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.0628(16) _cell_length_b 4.7489(3) _cell_length_c 19.1950(13) _cell_angle_alpha 90.00 _cell_angle_beta 102.636(4) _cell_angle_gamma 90.00 _cell_volume 2140.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 7.840 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.375 _exptl_absorpt_correction_T_max 0.457 _exptl_absorpt_process_details Process-auto _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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5760 _diffrn_reflns_av_R_equivalents 0.0749 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.03 _reflns_number_total 1899 _reflns_number_gt 1718 _reflns_threshold_expression >2sigma(I) _computing_data_collection Process-auto _computing_cell_refinement Process-auto _computing_data_reduction Process-auto _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0859P)^2^+4.1233P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1899 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1344 _refine_ls_wR_factor_gt 0.1304 _refine_ls_goodness_of_fit_ref 1.160 _refine_ls_restrained_S_all 1.160 _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 1.0000 0.87600(14) 0.2500 0.0344(2) Uani 1 2 d S . . Se1 Se 0.96312(3) 0.56007(14) 0.34675(3) 0.0375(2) Uani 1 1 d . . . Se2 Se 1.08629(3) 1.18434(14) 0.31927(3) 0.0403(3) Uani 1 1 d . . . C1 C 1.0173(3) 0.6616(16) 0.4251(4) 0.0456(17) Uani 1 1 d . . . C2 C 1.1397(3) 0.9762(17) 0.2866(4) 0.0455(17) Uani 1 1 d . . . C3 C 0.8338(3) 0.8875(15) 0.4575(4) 0.0469(16) Uani 1 1 d . . . H3A H 0.8597 0.8139 0.4995 0.056 Uiso 1 1 calc R . . H3B H 0.8145 0.7293 0.4306 0.056 Uiso 1 1 calc R . . C4 C 0.7906(3) 1.0743(11) 0.4802(3) 0.0343(13) Uani 1 1 d . . . C5 C 0.8056(3) 1.2530(15) 0.5387(4) 0.0402(14) Uani 1 1 d . . . H5A H 0.8430 1.2551 0.5651 0.048 Uiso 1 1 calc R . . C6 C 0.7660(3) 1.4257(13) 0.5579(3) 0.0373(14) Uani 1 1 d . . . H6A H 0.7769 1.5450 0.5969 0.045 Uiso 1 1 calc R . . N1 N 1.0524(3) 0.7109(19) 0.4751(4) 0.074(2) Uani 1 1 d . . . N2 N 1.1731(3) 0.8441(19) 0.2668(4) 0.071(2) Uani 1 1 d . . . N3 N 0.8672(2) 1.0431(12) 0.4124(3) 0.0410(13) Uani 1 1 d . . . H3C H 0.8923 0.9270 0.3998 0.080 Uiso 1 1 calc . . . H3D H 0.8855 1.1864 0.4372 0.080 Uiso 1 1 calc . . . H3E H 0.8436 1.1083 0.3734 0.080 Uiso 1 1 calc . . . OW1 O 0.2958(2) 0.0784(13) 0.8227(3) 0.0638(16) 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 0.0232(4) 0.0483(4) 0.0324(4) 0.000 0.0075(3) 0.000 Se1 0.0314(4) 0.0481(4) 0.0339(4) 0.0000(2) 0.0087(3) -0.0076(3) Se2 0.0322(4) 0.0427(4) 0.0435(4) -0.0017(3) 0.0025(3) -0.0024(3) C1 0.032(4) 0.066(4) 0.041(4) 0.002(3) 0.013(3) -0.012(3) C2 0.026(3) 0.064(4) 0.044(4) 0.005(3) 0.003(3) -0.010(3) C3 0.043(4) 0.042(3) 0.059(4) 0.004(3) 0.018(3) 0.007(3) C4 0.039(4) 0.027(3) 0.038(3) 0.004(2) 0.012(3) 0.000(2) C5 0.031(3) 0.052(4) 0.036(3) 0.006(3) 0.004(3) -0.001(3) C6 0.037(4) 0.039(3) 0.036(3) -0.004(2) 0.008(3) -0.007(3) N1 0.060(5) 0.113(6) 0.046(4) 0.004(4) 0.004(4) -0.036(5) N2 0.032(3) 0.101(6) 0.081(5) -0.010(4) 0.015(3) 0.010(4) N3 0.035(3) 0.052(3) 0.037(3) -0.005(2) 0.010(2) 0.004(2) OW1 0.044(3) 0.081(4) 0.063(4) -0.015(3) 0.004(3) 0.004(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 Cd1 Se2 2.6487(7) . ? Cd1 Se2 2.6487(7) 2_755 ? Cd1 Se1 2.6848(7) 2_755 ? Cd1 Se1 2.6848(7) . ? Se1 C1 1.826(7) . ? Se2 C2 1.838(8) . ? C1 N1 1.155(9) . ? C2 N2 1.148(11) . ? C3 N3 1.498(10) . ? C3 C4 1.502(9) . ? C4 C5 1.391(10) . ? C4 C6 1.398(10) 7_676 ? C5 C6 1.368(10) . ? C6 C4 1.398(10) 7_676 ? 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 Se2 Cd1 Se2 112.88(4) . 2_755 ? Se2 Cd1 Se1 108.34(2) . 2_755 ? Se2 Cd1 Se1 107.65(2) 2_755 2_755 ? Se2 Cd1 Se1 107.65(2) . . ? Se2 Cd1 Se1 108.34(2) 2_755 . ? Se1 Cd1 Se1 112.05(4) 2_755 . ? C1 Se1 Cd1 97.9(2) . . ? C2 Se2 Cd1 93.5(2) . . ? N1 C1 Se1 176.3(8) . . ? N2 C2 Se2 179.2(8) . . ? N3 C3 C4 111.7(5) . . ? C5 C4 C6 118.3(6) . 7_676 ? C5 C4 C3 121.4(6) . . ? C6 C4 C3 120.3(6) 7_676 . ? C6 C5 C4 120.6(6) . . ? C5 C6 C4 121.1(6) . 7_676 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.921 _refine_diff_density_min -1.502 _refine_diff_density_rms 0.248 _database_code_depnum_ccdc_archive 'CCDC 934339' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_6 #TrackingRef '6.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 Br6 Cd2 N2 O0 S2' _chemical_formula_weight 926.56 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' Br Br -0.2901 2.4595 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.862(5) _cell_length_b 4.0296(8) _cell_length_c 20.735(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.48(3) _cell_angle_gamma 90.00 _cell_volume 1930.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1688 _exptl_absorpt_coefficient_mu 14.833 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.213 _exptl_absorpt_correction_T_max 0.227 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 8647 _diffrn_reflns_av_R_equivalents 0.1095 _diffrn_reflns_av_sigmaI/netI 0.1040 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2197 _reflns_number_gt 1937 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMAR' _computing_cell_refinement 'Bruker SMAR' _computing_data_reduction 'Bruker SMAR' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0519P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2197 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1183 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 0.199821(18) 0.53916(11) 0.163697(19) 0.01004(17) Uani 1 1 d . . . Br1 Br 0.09074(3) 0.51377(12) 0.09158(3) 0.01118(18) Uani 1 1 d . . . Br2 Br 0.23413(2) 0.04953(13) 0.09103(3) 0.00944(18) Uani 1 1 d . . . Br3 Br 0.18287(2) 1.02147(12) 0.25082(3) 0.00883(18) Uani 1 1 d . . . S1 S 0.04432(6) 0.4237(3) 0.26192(7) 0.0138(3) Uani 1 1 d . . . N1 N 0.1026(2) -0.0281(10) 0.4646(3) 0.0153(11) Uani 1 1 d . . . H1A H 0.1150 -0.1081 0.5041 0.018 Uiso 1 1 calc R . . C1 C 0.1396(2) 0.1341(14) 0.4375(3) 0.0149(11) Uani 1 1 d . . . H1B H 0.1783 0.1535 0.4607 0.018 Uiso 1 1 calc R . . C2 C 0.1207(2) 0.2730(14) 0.3752(2) 0.0144(11) Uani 1 1 d . . . H2A H 0.1461 0.3911 0.3563 0.017 Uiso 1 1 calc R . . C3 C 0.0625(2) 0.2336(12) 0.3405(2) 0.0087(10) Uani 1 1 d . . . C4 C 0.0252(3) 0.0579(12) 0.3708(3) 0.0115(12) Uani 1 1 d . . . H4A H -0.0136 0.0298 0.3490 0.014 Uiso 1 1 calc R . . C5 C 0.0471(3) -0.0715(13) 0.4332(3) 0.0130(12) Uani 1 1 d . . . H5B H 0.0230 -0.1907 0.4537 0.016 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 0.0140(3) 0.0089(3) 0.0064(3) -0.00111(13) 0.00088(18) 0.00095(13) Br1 0.0123(3) 0.0117(3) 0.0089(3) -0.0003(2) 0.0015(2) 0.00083(19) Br2 0.0116(3) 0.0104(3) 0.0061(3) -0.00075(19) 0.0017(2) 0.00124(18) Br3 0.0122(3) 0.0093(3) 0.0047(3) -0.00095(18) 0.0015(2) 0.00051(17) S1 0.0144(7) 0.0181(7) 0.0072(7) 0.0020(6) -0.0007(5) -0.0042(5) N1 0.025(3) 0.013(2) 0.007(3) 0.0007(18) 0.002(2) 0.0009(19) C1 0.013(3) 0.022(3) 0.010(3) -0.003(2) 0.002(2) -0.005(2) C2 0.014(3) 0.019(3) 0.010(3) -0.004(2) 0.003(2) -0.004(2) C3 0.013(2) 0.007(2) 0.007(2) -0.001(2) 0.0038(19) -0.002(2) C4 0.013(3) 0.015(3) 0.007(3) -0.001(2) 0.003(2) 0.001(2) C5 0.015(3) 0.013(3) 0.012(3) -0.003(2) 0.004(2) -0.001(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 Br1 2.6599(11) . ? Cd1 Br2 2.7295(7) . ? Cd1 Br3 2.7512(7) . ? Cd1 Br2 2.7906(7) 1_565 ? Cd1 Br3 2.8537(7) 1_545 ? Cd1 Br3 2.9157(12) 4_545 ? Br2 Cd1 2.7906(7) 1_545 ? Br3 Cd1 2.8537(7) 1_565 ? Br3 Cd1 2.9157(12) 4 ? S1 C3 1.754(5) . ? S1 S1 2.048(3) 2 ? N1 C1 1.332(8) . ? N1 C5 1.333(8) . ? N1 H1A 0.8600 . ? C1 C2 1.377(7) . ? C1 H1B 0.9300 . ? C2 C3 1.405(6) . ? C2 H2A 0.9300 . ? C3 C4 1.402(7) . ? C4 C5 1.371(8) . ? C4 H4A 0.9300 . ? C5 H5B 0.9300 . ? 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 Br1 Cd1 Br2 92.76(2) . . ? Br1 Cd1 Br3 96.46(3) . . ? Br2 Cd1 Br3 170.65(2) . . ? Br1 Cd1 Br2 95.90(2) . 1_565 ? Br2 Cd1 Br2 93.76(3) . 1_565 ? Br3 Cd1 Br2 86.85(2) . 1_565 ? Br1 Cd1 Br3 93.10(3) . 1_545 ? Br2 Cd1 Br3 86.02(2) . 1_545 ? Br3 Cd1 Br3 91.92(3) . 1_545 ? Br2 Cd1 Br3 171.00(2) 1_565 1_545 ? Br1 Cd1 Br3 175.27(2) . 4_545 ? Br2 Cd1 Br3 86.74(2) . 4_545 ? Br3 Cd1 Br3 83.94(3) . 4_545 ? Br2 Cd1 Br3 88.83(2) 1_565 4_545 ? Br3 Cd1 Br3 82.17(2) 1_545 4_545 ? Cd1 Br2 Cd1 93.76(3) . 1_545 ? Cd1 Br3 Cd1 91.92(3) . 1_565 ? Cd1 Br3 Cd1 98.05(3) . 4 ? Cd1 Br3 Cd1 95.77(3) 1_565 4 ? C3 S1 S1 103.00(19) . 2 ? C1 N1 C5 122.7(5) . . ? C1 N1 H1A 118.6 . . ? C5 N1 H1A 118.6 . . ? N1 C1 C2 120.0(5) . . ? N1 C1 H1B 120.0 . . ? C2 C1 H1B 120.0 . . ? C1 C2 C3 119.0(5) . . ? C1 C2 H2A 120.5 . . ? C3 C2 H2A 120.5 . . ? C4 C3 C2 119.0(5) . . ? C4 C3 S1 126.8(4) . . ? C2 C3 S1 114.2(4) . . ? C5 C4 C3 118.7(5) . . ? C5 C4 H4A 120.7 . . ? C3 C4 H4A 120.7 . . ? N1 C5 C4 120.6(6) . . ? N1 C5 H5B 119.7 . . ? C4 C5 H5B 119.7 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 2.493 _refine_diff_density_min -3.414 _refine_diff_density_rms 0.577 _database_code_depnum_ccdc_archive 'CCDC 934340'