# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H25 Br4 Cd N4 O6.50 S5' _chemical_formula_weight 1017.78 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' 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 triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3299(11) _cell_length_b 11.3904(13) _cell_length_c 16.6994(13) _cell_angle_alpha 96.644(6) _cell_angle_beta 98.656(7) _cell_angle_gamma 97.835(7) _cell_volume 1721.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 824 _cell_measurement_theta_min 2.8756 _cell_measurement_theta_max 24.3256 _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 1.964 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 986 _exptl_absorpt_coefficient_mu 5.621 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.486 _exptl_absorpt_correction_T_max 0.570 _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 9739 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0575 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.14 _reflns_number_total 6027 _reflns_number_gt 3988 _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 '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^)+(0.0839P)^2^+1.6388P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6027 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0815 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1634 _refine_ls_wR_factor_gt 0.1523 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 0.04766(7) 0.25627(7) 0.19181(3) 0.0685(2) Uani 1 1 d . . . Br1 Br 0.08996(17) 0.3973(2) 0.08277(10) 0.1793(10) Uani 1 1 d . . . Br2 Br 0.30336(9) 0.26664(8) 0.27705(5) 0.0655(3) Uani 1 1 d . . . Br3 Br -0.13878(10) 0.33603(8) 0.27373(5) 0.0662(3) Uani 1 1 d . . . Br4 Br -0.06751(12) 0.03437(13) 0.13203(8) 0.1134(5) Uani 1 1 d . . . S1 S -0.0706(2) 0.25342(17) 0.50767(12) 0.0523(5) Uani 1 1 d . . . S2 S 0.1053(2) 0.33594(18) 0.59106(11) 0.0537(5) Uani 1 1 d . . . S3 S 0.4269(3) 0.19007(18) -0.02218(11) 0.0587(5) Uani 1 1 d . . . S4 S 0.6230(3) 0.29999(19) -0.00668(13) 0.0647(6) Uani 1 1 d . . . S5 S 0.5013(2) 0.20635(15) 0.66049(10) 0.0440(4) Uani 1 1 d . . . N1 N 0.0707(7) -0.0381(6) 0.3486(4) 0.0557(16) Uani 1 1 d . . . H1A H 0.0957 -0.0936 0.3165 0.067 Uiso 1 1 calc R . . C8 C 0.2572(9) 0.5257(7) 0.4235(4) 0.0519(19) Uani 1 1 d . . . H8A H 0.2397 0.5296 0.3676 0.062 Uiso 1 1 calc R . . N3 N 0.4386(8) -0.0024(6) 0.1972(4) 0.0570(17) Uani 1 1 d . . . H3A H 0.4382 -0.0386 0.2396 0.068 Uiso 1 1 calc R . . N4 N 0.6150(7) 0.6069(5) 0.1868(4) 0.0528(16) Uani 1 1 d . . . H4A H 0.6166 0.6662 0.2239 0.063 Uiso 1 1 calc R . . C1 C -0.1105(9) 0.0635(7) 0.3909(5) 0.059(2) Uani 1 1 d . . . H1B H -0.2085 0.0736 0.3864 0.071 Uiso 1 1 calc R . . C2 C -0.0698(10) -0.0259(7) 0.3422(5) 0.062(2) Uani 1 1 d . . . H2A H -0.1402 -0.0783 0.3045 0.074 Uiso 1 1 calc R . . C3 C 0.1736(9) 0.0328(8) 0.4028(5) 0.064(2) Uani 1 1 d . . . H3B H 0.2707 0.0205 0.4059 0.076 Uiso 1 1 calc R . . C4 C 0.1405(8) 0.1241(7) 0.4546(5) 0.0529(19) Uani 1 1 d . . . H4B H 0.2132 0.1733 0.4929 0.063 Uiso 1 1 calc R . . C5 C -0.0032(7) 0.1399(6) 0.4479(4) 0.0418(16) Uani 1 1 d . . . C6 C 0.3194(8) 0.5169(6) 0.5865(4) 0.0469(17) Uani 1 1 d . . . H6A H 0.3435 0.5135 0.6422 0.056 Uiso 1 1 calc R . . C7 C 0.3977(8) 0.5985(7) 0.5512(5) 0.0510(18) Uani 1 1 d . . . H7A H 0.4740 0.6530 0.5831 0.061 Uiso 1 1 calc R . . N2 N 0.3668(7) 0.6017(5) 0.4718(4) 0.0505(15) Uani 1 1 d . . . H2B H 0.4186 0.6541 0.4504 0.061 Uiso 1 1 calc R . . C9 C 0.1707(9) 0.4423(6) 0.4554(4) 0.0490(18) Uani 1 1 d . . . H9A H 0.0933 0.3904 0.4223 0.059 Uiso 1 1 calc R . . C10 C 0.2029(8) 0.4379(6) 0.5395(4) 0.0426(16) Uani 1 1 d . . . C11 C 0.3191(10) -0.0194(7) 0.1402(6) 0.066(2) Uani 1 1 d . . . H11A H 0.2363 -0.0706 0.1466 0.079 Uiso 1 1 calc R . . C12 C 0.3160(9) 0.0384(7) 0.0712(5) 0.058(2) Uani 1 1 d . . . H12A H 0.2331 0.0261 0.0308 0.069 Uiso 1 1 calc R . . C13 C 0.4401(8) 0.1142(6) 0.0649(4) 0.0443(17) Uani 1 1 d . . . C14 C 0.5628(9) 0.1302(7) 0.1252(5) 0.0538(19) Uani 1 1 d . . . H14A H 0.6472 0.1819 0.1217 0.065 Uiso 1 1 calc R . . C15 C 0.5566(9) 0.0684(7) 0.1896(5) 0.0553(19) Uani 1 1 d . . . H15A H 0.6394 0.0768 0.2297 0.066 Uiso 1 1 calc R . . C16 C 0.7295(10) 0.5081(7) 0.0888(5) 0.060(2) Uani 1 1 d . . . H16A H 0.8101 0.5048 0.0625 0.072 Uiso 1 1 calc R . . C17 C 0.7285(10) 0.6017(8) 0.1477(5) 0.067(2) Uani 1 1 d . . . H17A H 0.8086 0.6628 0.1607 0.081 Uiso 1 1 calc R . . C18 C 0.4966(9) 0.5192(7) 0.1683(5) 0.056(2) Uani 1 1 d . . . H18A H 0.4174 0.5234 0.1958 0.068 Uiso 1 1 calc R . . C19 C 0.4936(9) 0.4247(6) 0.1094(4) 0.0528(19) Uani 1 1 d . . . H19A H 0.4124 0.3646 0.0969 0.063 Uiso 1 1 calc R . . C20 C 0.6087(8) 0.4180(6) 0.0688(4) 0.0439(17) Uani 1 1 d . . . O1 O 0.3784(6) 0.2023(5) 0.7058(3) 0.0624(15) Uani 1 1 d . . . O2 O 0.6161(6) 0.3081(4) 0.6980(3) 0.0553(13) Uani 1 1 d . . . O3 O 0.4529(6) 0.2205(5) 0.5744(3) 0.0569(13) Uani 1 1 d . . . O4 O 0.5605(6) 0.0932(4) 0.6629(3) 0.0579(14) Uani 1 1 d . . . OW1 O 0.1149(7) -0.2325(6) 0.2540(4) 0.094(2) Uani 1 1 d . . . OW2 O 0.5855(8) 0.1069(6) 0.4518(5) 0.102(2) Uani 1 1 d . . . OW3 O -0.0239(15) 0.2408(13) -0.0866(8) 0.095(4) Uani 0.50 1 d P . . 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 0.0473(4) 0.1191(6) 0.0427(3) 0.0102(3) 0.0087(3) 0.0249(4) Br1 0.0957(10) 0.356(3) 0.1417(13) 0.1626(17) 0.0550(9) 0.0830(14) Br2 0.0519(5) 0.0805(6) 0.0577(5) -0.0060(4) -0.0051(4) 0.0170(4) Br3 0.0573(5) 0.0856(6) 0.0547(5) -0.0072(4) 0.0130(4) 0.0178(5) Br4 0.0661(7) 0.1445(11) 0.1043(8) -0.0615(8) -0.0145(6) 0.0266(7) S1 0.0427(10) 0.0502(11) 0.0650(12) 0.0052(9) 0.0123(9) 0.0095(9) S2 0.0624(13) 0.0557(12) 0.0425(10) 0.0123(8) 0.0097(9) 0.0021(10) S3 0.0827(15) 0.0507(11) 0.0426(10) 0.0056(8) 0.0056(10) 0.0163(10) S4 0.0877(16) 0.0543(12) 0.0624(12) 0.0062(10) 0.0405(12) 0.0182(11) S5 0.0484(10) 0.0392(10) 0.0431(9) 0.0006(7) 0.0100(8) 0.0043(8) N1 0.057(4) 0.053(4) 0.057(4) 0.006(3) 0.014(3) 0.006(3) C8 0.066(5) 0.051(5) 0.044(4) 0.010(3) 0.020(4) 0.014(4) N3 0.071(5) 0.058(4) 0.049(4) 0.012(3) 0.016(4) 0.025(4) N4 0.059(4) 0.046(4) 0.051(4) -0.002(3) 0.010(3) 0.007(3) C1 0.043(4) 0.067(5) 0.067(5) 0.006(4) 0.009(4) 0.010(4) C2 0.068(6) 0.054(5) 0.056(5) 0.003(4) 0.004(4) -0.001(4) C3 0.044(5) 0.064(5) 0.088(6) 0.016(5) 0.018(5) 0.017(4) C4 0.044(4) 0.053(5) 0.059(5) 0.002(4) 0.010(4) 0.004(4) C5 0.037(4) 0.040(4) 0.051(4) 0.014(3) 0.011(3) 0.003(3) C6 0.044(4) 0.050(4) 0.043(4) -0.006(3) -0.002(3) 0.012(4) C7 0.045(4) 0.047(4) 0.055(5) -0.004(4) 0.002(4) 0.006(4) N2 0.046(4) 0.041(3) 0.069(4) 0.009(3) 0.020(3) 0.010(3) C9 0.062(5) 0.040(4) 0.041(4) 0.001(3) 0.008(3) 0.002(4) C10 0.050(4) 0.043(4) 0.038(4) 0.007(3) 0.013(3) 0.013(3) C11 0.064(6) 0.053(5) 0.085(6) 0.010(4) 0.033(5) 0.004(4) C12 0.052(5) 0.062(5) 0.058(5) 0.011(4) 0.004(4) 0.007(4) C13 0.057(5) 0.035(4) 0.041(4) 0.001(3) 0.009(3) 0.008(3) C14 0.046(4) 0.055(5) 0.059(5) 0.010(4) 0.001(4) 0.008(4) C15 0.055(5) 0.053(5) 0.055(5) 0.010(4) -0.004(4) 0.013(4) C16 0.064(5) 0.059(5) 0.065(5) 0.015(4) 0.030(4) 0.014(4) C17 0.056(5) 0.060(5) 0.086(6) 0.010(5) 0.023(5) -0.001(4) C18 0.058(5) 0.059(5) 0.056(5) 0.006(4) 0.021(4) 0.013(4) C19 0.051(5) 0.045(4) 0.061(5) -0.002(4) 0.015(4) 0.005(4) C20 0.050(4) 0.049(4) 0.041(4) 0.012(3) 0.018(3) 0.021(4) O1 0.058(3) 0.057(3) 0.069(3) -0.004(3) 0.024(3) -0.003(3) O2 0.054(3) 0.047(3) 0.059(3) -0.006(2) 0.012(3) -0.004(2) O3 0.063(3) 0.057(3) 0.047(3) 0.010(2) -0.001(3) 0.006(3) O4 0.078(4) 0.045(3) 0.055(3) 0.008(2) 0.016(3) 0.019(3) OW1 0.072(4) 0.083(4) 0.117(5) -0.023(4) 0.010(4) 0.018(4) OW2 0.087(5) 0.094(5) 0.119(6) -0.013(4) 0.036(4) -0.008(4) OW3 0.087(10) 0.102(10) 0.075(8) 0.012(7) -0.009(7) -0.033(8) _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 Br3 2.5656(10) . ? Cd1 Br2 2.5678(10) . ? Cd1 Br1 2.6020(16) . ? Cd1 Br4 2.6253(15) . ? S1 C5 1.782(7) . ? S1 S2 2.026(3) . ? S2 C10 1.761(7) . ? S3 C13 1.773(7) . ? S3 S4 2.035(3) . ? S4 C20 1.767(7) . ? S5 O1 1.465(5) . ? S5 O4 1.471(5) . ? S5 O3 1.474(5) . ? S5 O2 1.475(5) . ? N1 C3 1.323(10) . ? N1 C2 1.327(10) . ? C8 N2 1.339(10) . ? C8 C9 1.369(10) . ? N3 C15 1.305(10) . ? N3 C11 1.328(11) . ? N4 C17 1.329(10) . ? N4 C18 1.355(10) . ? C1 C2 1.360(11) . ? C1 C5 1.396(10) . ? C3 C4 1.373(11) . ? C4 C5 1.367(10) . ? C6 C7 1.347(10) . ? C6 C10 1.386(10) . ? C7 N2 1.321(9) . ? C9 C10 1.400(9) . ? C11 C12 1.391(11) . ? C12 C13 1.371(11) . ? C13 C14 1.383(10) . ? C14 C15 1.355(10) . ? C16 C17 1.366(11) . ? C16 C20 1.388(11) . ? C18 C19 1.367(10) . ? C19 C20 1.359(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 Br3 Cd1 Br2 113.71(3) . . ? Br3 Cd1 Br1 107.50(5) . . ? Br2 Cd1 Br1 104.38(5) . . ? Br3 Cd1 Br4 105.45(4) . . ? Br2 Cd1 Br4 111.09(4) . . ? Br1 Cd1 Br4 114.90(7) . . ? C5 S1 S2 105.0(2) . . ? C10 S2 S1 105.3(2) . . ? C13 S3 S4 104.0(3) . . ? C20 S4 S3 104.3(3) . . ? O1 S5 O4 108.5(3) . . ? O1 S5 O3 111.0(3) . . ? O4 S5 O3 108.8(3) . . ? O1 S5 O2 109.8(3) . . ? O4 S5 O2 110.2(3) . . ? O3 S5 O2 108.6(3) . . ? C3 N1 C2 121.9(7) . . ? N2 C8 C9 120.8(7) . . ? C15 N3 C11 120.9(7) . . ? C17 N4 C18 120.4(7) . . ? C2 C1 C5 119.1(8) . . ? N1 C2 C1 119.8(8) . . ? N1 C3 C4 121.6(8) . . ? C5 C4 C3 117.4(7) . . ? C4 C5 C1 120.2(7) . . ? C4 C5 S1 125.1(6) . . ? C1 C5 S1 114.7(5) . . ? C7 C6 C10 119.8(7) . . ? N2 C7 C6 120.5(7) . . ? C7 N2 C8 121.9(7) . . ? C8 C9 C10 117.7(7) . . ? C6 C10 C9 119.2(7) . . ? C6 C10 S2 116.6(5) . . ? C9 C10 S2 124.1(6) . . ? N3 C11 C12 120.9(8) . . ? C13 C12 C11 117.4(8) . . ? C12 C13 C14 120.4(7) . . ? C12 C13 S3 115.3(6) . . ? C14 C13 S3 124.3(6) . . ? C15 C14 C13 118.1(7) . . ? N3 C15 C14 122.3(7) . . ? C17 C16 C20 119.2(7) . . ? N4 C17 C16 121.1(8) . . ? N4 C18 C19 120.0(7) . . ? C20 C19 C18 120.4(7) . . ? C19 C20 C16 118.9(7) . . ? C19 C20 S4 125.6(6) . . ? C16 C20 S4 115.5(5) . . ? 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 N4 H4A O1 0.86 1.78 2.641(8) 174.9 2_666 N3 H3A O4 0.86 1.81 2.662(8) 171.7 2_656 _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.14 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 1.845 _refine_diff_density_min -2.000 _refine_diff_density_rms 0.118 _database_code_depnum_ccdc_archive 'CCDC 966912' ####################################################################### # # 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 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 Br4 Cd Cl0 N4 O0 S4' _chemical_formula_weight 874.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3666(5) _cell_length_b 9.4698(6) _cell_length_c 18.8322(11) _cell_angle_alpha 95.118(4) _cell_angle_beta 99.093(4) _cell_angle_gamma 117.228(3) _cell_volume 1441.62(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 895 _cell_measurement_theta_min 2.5067 _cell_measurement_theta_max 23.1519 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.015 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 836 _exptl_absorpt_coefficient_mu 6.607 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.457 _exptl_absorpt_correction_T_max 0.552 _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 6962 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 23.25 _reflns_number_total 4123 _reflns_number_gt 3050 _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 '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^)+(0.0150P)^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 4123 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0531 _refine_ls_wR_factor_gt 0.0505 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 0.25214(4) 0.73906(4) 0.244432(19) 0.04611(12) Uani 1 1 d . . . Br1 Br -0.00979(6) 0.61196(7) 0.29698(3) 0.06036(17) Uani 1 1 d . . . Br2 Br 0.42475(6) 1.04564(6) 0.29094(3) 0.05795(16) Uani 1 1 d . . . Br3 Br 0.44240(6) 0.61497(7) 0.28034(3) 0.06028(17) Uani 1 1 d . . . Br4 Br 0.13738(6) 0.68657(6) 0.10372(3) 0.05233(15) Uani 1 1 d . . . N1 N 0.4670(5) 1.3289(5) 0.4392(2) 0.0508(11) Uani 1 1 d . . . N2 N 0.1451(5) 1.2021(6) 0.3773(2) 0.0587(12) Uani 1 1 d . . . N3 N 0.1191(5) 0.9393(5) -0.0698(2) 0.0502(11) Uani 1 1 d . . . N4 N 0.4095(5) 1.1253(5) 0.0258(2) 0.0475(11) Uani 1 1 d . . . C1 C 0.5982(6) 1.4203(6) 0.4159(3) 0.0599(15) Uani 1 1 d . . . H1B H 0.5862 1.4684 0.3761 0.072 Uiso 1 1 calc R . . C2 C 0.7520(7) 1.4475(8) 0.4481(3) 0.080(2) Uani 1 1 d . . . H2B H 0.8428 1.5103 0.4297 0.096 Uiso 1 1 calc R . . C3 C 0.7696(7) 1.3803(9) 0.5082(4) 0.101(2) Uani 1 1 d . . . H3B H 0.8739 1.4032 0.5332 0.121 Uiso 1 1 calc R . . C4 C 0.6321(7) 1.2786(8) 0.5314(3) 0.0780(18) Uani 1 1 d . . . H4B H 0.6404 1.2269 0.5703 0.094 Uiso 1 1 calc R . . C5 C 0.4835(6) 1.2565(6) 0.4952(3) 0.0549(14) Uani 1 1 d . . . C6 C 0.0717(7) 1.2734(7) 0.3393(3) 0.0705(17) Uani 1 1 d . . . H6A H 0.1315 1.3830 0.3386 0.085 Uiso 1 1 calc R . . C7 C -0.0890(6) 1.1890(7) 0.3017(4) 0.0791(19) Uani 1 1 d . . . H7A H -0.1381 1.2402 0.2755 0.095 Uiso 1 1 calc R . . C8 C -0.1757(6) 1.0295(8) 0.3031(3) 0.0751(18) Uani 1 1 d . . . H8A H -0.2850 0.9702 0.2777 0.090 Uiso 1 1 calc R . . C9 C -0.1015(6) 0.9549(7) 0.3425(3) 0.0630(16) Uani 1 1 d . . . H9A H -0.1595 0.8450 0.3431 0.076 Uiso 1 1 calc R . . C10 C 0.0595(6) 1.0457(7) 0.3808(3) 0.0510(14) Uani 1 1 d . . . C11 C 0.0092(6) 0.7832(6) -0.0751(3) 0.0595(15) Uani 1 1 d . . . H11A H 0.0346 0.7215 -0.0449 0.071 Uiso 1 1 calc R . . C12 C -0.1412(6) 0.7123(7) -0.1246(3) 0.0623(16) Uani 1 1 d . . . H12A H -0.2172 0.6048 -0.1270 0.075 Uiso 1 1 calc R . . C13 C -0.1772(6) 0.8031(7) -0.1706(3) 0.0676(16) Uani 1 1 d . . . H13A H -0.2782 0.7575 -0.2039 0.081 Uiso 1 1 calc R . . C14 C -0.0628(6) 0.9609(7) -0.1667(3) 0.0596(15) Uani 1 1 d . . . H14A H -0.0839 1.0231 -0.1980 0.072 Uiso 1 1 calc R . . C15 C 0.0837(6) 1.0257(6) -0.1157(3) 0.0502(13) Uani 1 1 d . . . C16 C 0.4519(6) 1.1233(6) 0.0967(3) 0.0584(15) Uani 1 1 d . . . H16A H 0.3790 1.0409 0.1168 0.070 Uiso 1 1 calc R . . C17 C 0.5972(6) 1.2369(7) 0.1403(3) 0.0647(16) Uani 1 1 d . . . H17A H 0.6245 1.2326 0.1894 0.078 Uiso 1 1 calc R . . C18 C 0.7032(6) 1.3586(7) 0.1101(3) 0.0634(16) Uani 1 1 d . . . H18A H 0.8039 1.4381 0.1388 0.076 Uiso 1 1 calc R . . C19 C 0.6599(6) 1.3628(6) 0.0372(3) 0.0534(14) Uani 1 1 d . . . H19A H 0.7308 1.4446 0.0162 0.064 Uiso 1 1 calc R . . C20 C 0.5104(6) 1.2442(6) -0.0038(3) 0.0458(13) Uani 1 1 d . . . S1 S 0.30174(18) 1.13519(19) 0.52531(8) 0.0728(5) Uani 1 1 d . . . S2 S 0.15822(17) 0.95902(17) 0.43509(8) 0.0648(4) Uani 1 1 d . . . S3 S 0.22569(17) 1.23382(17) -0.10577(9) 0.0690(4) Uani 1 1 d . . . S4 S 0.45037(16) 1.24207(18) -0.09817(7) 0.0617(4) Uani 1 1 d . . . H4A H 0.286(6) 1.037(6) -0.012(3) 0.093(17) Uiso 1 1 d . . . H2A H 0.275(9) 1.273(8) 0.404(4) 0.16(3) 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 0.0443(2) 0.0460(2) 0.0441(2) 0.01075(18) 0.00289(18) 0.02011(18) Br1 0.0518(3) 0.0639(4) 0.0570(4) 0.0121(3) 0.0151(3) 0.0197(3) Br2 0.0570(3) 0.0456(3) 0.0603(4) 0.0049(3) 0.0078(3) 0.0180(3) Br3 0.0506(3) 0.0525(4) 0.0715(4) 0.0136(3) -0.0039(3) 0.0246(3) Br4 0.0523(3) 0.0577(4) 0.0409(3) 0.0101(3) 0.0043(3) 0.0231(3) N1 0.042(3) 0.055(3) 0.051(3) 0.013(2) 0.006(2) 0.021(2) N2 0.040(3) 0.060(3) 0.071(3) 0.013(3) 0.003(3) 0.023(3) N3 0.046(3) 0.042(3) 0.055(3) 0.005(2) -0.002(2) 0.019(2) N4 0.032(2) 0.046(3) 0.051(3) 0.010(2) 0.004(2) 0.010(2) C1 0.058(4) 0.061(4) 0.055(4) 0.016(3) 0.007(3) 0.025(3) C2 0.048(4) 0.112(6) 0.072(5) 0.039(4) 0.013(3) 0.027(3) C3 0.043(4) 0.148(7) 0.104(6) 0.061(5) 0.001(4) 0.038(4) C4 0.069(4) 0.106(5) 0.060(4) 0.029(4) 0.004(4) 0.043(4) C5 0.055(4) 0.058(4) 0.041(3) -0.003(3) 0.007(3) 0.022(3) C6 0.056(4) 0.052(4) 0.097(5) 0.017(3) 0.001(4) 0.026(3) C7 0.045(3) 0.067(5) 0.117(6) 0.030(4) -0.001(4) 0.023(3) C8 0.038(3) 0.077(5) 0.101(5) 0.012(4) 0.007(3) 0.024(3) C9 0.046(3) 0.052(4) 0.076(4) 0.002(3) 0.021(3) 0.010(3) C10 0.044(3) 0.055(4) 0.055(4) 0.014(3) 0.015(3) 0.023(3) C11 0.058(3) 0.050(4) 0.062(4) 0.012(3) -0.003(3) 0.024(3) C12 0.048(3) 0.046(4) 0.070(4) -0.001(3) 0.000(3) 0.010(3) C13 0.048(3) 0.069(5) 0.078(4) 0.005(4) -0.002(3) 0.028(3) C14 0.059(3) 0.057(4) 0.068(4) 0.007(3) -0.002(3) 0.038(3) C15 0.043(3) 0.052(4) 0.056(4) 0.003(3) 0.004(3) 0.026(3) C16 0.042(3) 0.065(4) 0.059(4) 0.026(3) 0.015(3) 0.015(3) C17 0.047(3) 0.081(4) 0.047(4) 0.015(3) 0.007(3) 0.015(3) C18 0.046(3) 0.061(4) 0.063(4) 0.004(3) 0.001(3) 0.013(3) C19 0.040(3) 0.049(4) 0.059(4) 0.010(3) 0.017(3) 0.010(3) C20 0.045(3) 0.044(3) 0.048(3) 0.009(3) 0.017(3) 0.019(3) S1 0.0742(10) 0.0843(12) 0.0523(10) 0.0151(8) 0.0233(8) 0.0285(9) S2 0.0651(9) 0.0567(10) 0.0683(10) 0.0187(8) 0.0139(8) 0.0247(7) S3 0.0609(9) 0.0509(9) 0.0893(12) 0.0176(8) -0.0009(8) 0.0267(7) S4 0.0541(8) 0.0727(11) 0.0499(9) 0.0178(8) 0.0083(7) 0.0232(7) _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 Br2 2.5717(7) . ? Cd1 Br3 2.5868(7) . ? Cd1 Br1 2.5932(6) . ? Cd1 Br4 2.6077(6) . ? N1 C1 1.309(6) . ? N1 C5 1.334(6) . ? N2 C10 1.337(6) . ? N2 C6 1.340(6) . ? N3 C11 1.343(6) . ? N3 C15 1.345(6) . ? N4 C20 1.334(5) . ? N4 C16 1.335(6) . ? C1 C2 1.366(7) . ? C2 C3 1.370(8) . ? C3 C4 1.376(7) . ? C4 C5 1.362(7) . ? C5 S1 1.781(5) . ? C6 C7 1.367(7) . ? C7 C8 1.353(7) . ? C8 C9 1.383(7) . ? C9 C10 1.375(6) . ? C10 S2 1.766(5) . ? C11 C12 1.383(6) . ? C12 C13 1.381(7) . ? C13 C14 1.370(7) . ? C14 C15 1.375(6) . ? C15 S3 1.773(5) . ? C16 C17 1.354(6) . ? C17 C18 1.373(6) . ? C18 C19 1.378(7) . ? C19 C20 1.372(6) . ? C20 S4 1.772(5) . ? S1 S2 2.049(2) . ? S3 S4 2.051(2) . ? 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 Br2 Cd1 Br3 106.95(2) . . ? Br2 Cd1 Br1 112.21(2) . . ? Br3 Cd1 Br1 111.57(2) . . ? Br2 Cd1 Br4 108.75(2) . . ? Br3 Cd1 Br4 113.44(2) . . ? Br1 Cd1 Br4 104.00(2) . . ? C1 N1 C5 118.9(5) . . ? C10 N2 C6 120.0(5) . . ? C11 N3 C15 118.9(5) . . ? C20 N4 C16 119.9(4) . . ? N1 C1 C2 122.3(5) . . ? C1 C2 C3 118.6(5) . . ? C2 C3 C4 119.6(6) . . ? C5 C4 C3 117.5(6) . . ? N1 C5 C4 122.9(5) . . ? N1 C5 S1 117.1(4) . . ? C4 C5 S1 119.9(5) . . ? N2 C6 C7 121.6(6) . . ? C8 C7 C6 118.9(6) . . ? C7 C8 C9 120.0(5) . . ? C10 C9 C8 119.0(5) . . ? N2 C10 C9 120.4(5) . . ? N2 C10 S2 118.5(4) . . ? C9 C10 S2 121.1(5) . . ? N3 C11 C12 121.3(5) . . ? C13 C12 C11 119.3(5) . . ? C14 C13 C12 119.4(5) . . ? C13 C14 C15 118.8(5) . . ? N3 C15 C14 122.3(5) . . ? N3 C15 S3 118.6(4) . . ? C14 C15 S3 119.0(4) . . ? N4 C16 C17 122.3(5) . . ? C16 C17 C18 118.3(5) . . ? C17 C18 C19 119.8(5) . . ? C20 C19 C18 118.9(5) . . ? N4 C20 C19 120.7(5) . . ? N4 C20 S4 118.5(4) . . ? C19 C20 S4 120.7(4) . . ? C5 S1 S2 102.80(17) . . ? C10 S2 S1 104.69(19) . . ? C15 S3 S4 104.58(18) . . ? C20 S4 S3 102.45(16) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.391 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.072 _database_code_depnum_ccdc_archive 'CCDC 966913' ####################################################################### # # 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 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Cd Cl2 N10 O0 S2' _chemical_formula_weight 569.77 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' Cl Cl 0.1484 0.1585 '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 8.0161(16) _cell_length_b 17.660(4) _cell_length_c 8.0715(16) _cell_angle_alpha 90.00 _cell_angle_beta 113.90(3) _cell_angle_gamma 90.00 _cell_volume 1044.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9568 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 27.515 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.811 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 1.525 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.820 _exptl_absorpt_correction_T_max 0.846 _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 10106 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2392 _reflns_number_gt 2227 _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 '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^)+(0.0228P)^2^+0.5858P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2392 _refine_ls_number_parameters 133 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0236 _refine_ls_wR_factor_ref 0.0566 _refine_ls_wR_factor_gt 0.0559 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.157 _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 0.5000 0.0000 0.0000 0.02753(7) Uani 1 2 d S . . Cl1 Cl 0.23608(6) 0.03118(3) -0.32214(6) 0.03292(11) Uani 1 1 d . . . S1 S 0.69865(9) 0.27097(3) 0.10513(11) 0.05161(17) Uani 1 1 d . . . N1 N 0.1483(2) -0.10603(10) 0.3686(2) 0.0349(4) Uani 1 1 d . . . H1A H 0.0354 -0.0971 0.3448 0.042 Uiso 1 1 calc R . . N2 N 0.4177(2) -0.09614(10) 0.3765(2) 0.0364(4) Uani 1 1 d . . . H2A H 0.5104 -0.0797 0.3593 0.044 Uiso 1 1 calc R . . N3 N 0.3003(2) 0.04142(9) 0.1364(2) 0.0314(3) Uani 1 1 d . . . N4 N 0.0718(3) 0.05333(11) 0.2192(3) 0.0386(4) Uani 1 1 d . . . H4A H -0.0048 0.0427 0.2658 0.046 Uiso 1 1 calc R . . N5 N 0.6042(3) 0.12000(10) 0.0204(3) 0.0424(4) Uani 1 1 d . . . C1 C 0.4149(3) -0.16058(14) 0.4703(3) 0.0447(5) Uani 1 1 d . . . H1B H 0.5115 -0.1938 0.5262 0.054 Uiso 1 1 calc R . . C2 C 0.2463(3) -0.16659(13) 0.4661(3) 0.0427(5) Uani 1 1 d . . . H2B H 0.2041 -0.2046 0.5191 0.051 Uiso 1 1 calc R . . C3 C 0.2552(3) -0.06308(11) 0.3164(3) 0.0298(4) Uani 1 1 d . . . C4 C 0.2086(3) 0.00866(11) 0.2213(3) 0.0298(4) Uani 1 1 d . . . C5 C 0.0762(3) 0.11825(13) 0.1305(3) 0.0409(5) Uani 1 1 d . . . H5A H -0.0015 0.1596 0.1091 0.049 Uiso 1 1 calc R . . C6 C 0.2171(3) 0.11038(12) 0.0793(3) 0.0361(4) Uani 1 1 d . . . H6A H 0.2521 0.1462 0.0152 0.043 Uiso 1 1 calc R . . C7 C 0.6405(3) 0.18250(12) 0.0538(3) 0.0338(4) 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 0.02764(11) 0.02507(11) 0.03332(11) 0.00093(7) 0.01591(8) 0.00032(7) Cl1 0.0257(2) 0.0401(3) 0.0336(2) 0.0041(2) 0.01267(18) 0.00095(18) S1 0.0473(3) 0.0288(3) 0.0835(5) -0.0049(3) 0.0315(3) -0.0060(2) N1 0.0298(8) 0.0370(9) 0.0429(9) 0.0031(8) 0.0197(8) 0.0003(7) N2 0.0296(9) 0.0418(10) 0.0422(9) 0.0080(8) 0.0191(8) 0.0024(7) N3 0.0311(8) 0.0294(8) 0.0388(9) 0.0018(7) 0.0194(7) 0.0018(6) N4 0.0367(9) 0.0436(10) 0.0457(10) 0.0073(8) 0.0273(8) 0.0074(8) N5 0.0458(11) 0.0310(9) 0.0537(11) -0.0006(8) 0.0236(9) -0.0053(8) C1 0.0426(13) 0.0426(12) 0.0531(14) 0.0152(10) 0.0238(11) 0.0092(10) C2 0.0452(13) 0.0375(11) 0.0516(13) 0.0100(10) 0.0261(11) 0.0015(9) C3 0.0282(9) 0.0342(10) 0.0296(9) -0.0007(8) 0.0144(8) -0.0009(7) C4 0.0294(9) 0.0319(9) 0.0305(9) -0.0006(7) 0.0148(8) 0.0009(7) C5 0.0398(12) 0.0381(11) 0.0508(13) 0.0082(10) 0.0246(10) 0.0109(9) C6 0.0371(11) 0.0306(9) 0.0458(12) 0.0057(9) 0.0220(9) 0.0038(8) C7 0.0277(10) 0.0334(10) 0.0439(11) 0.0039(9) 0.0182(9) 0.0004(8) _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 N5 2.2592(18) 3_655 ? Cd1 N5 2.2592(19) . ? Cd1 N3 2.3952(17) 3_655 ? Cd1 N3 2.3952(17) . ? Cd1 Cl1 2.6613(12) 3_655 ? Cd1 Cl1 2.6613(12) . ? S1 C7 1.635(2) . ? N1 C3 1.334(3) . ? N1 C2 1.371(3) . ? N2 C3 1.327(3) . ? N2 C1 1.372(3) . ? N3 C4 1.324(3) . ? N3 C6 1.375(3) . ? N4 C4 1.345(3) . ? N4 C5 1.360(3) . ? N5 C7 1.146(3) . ? C1 C2 1.342(3) . ? C3 C4 1.450(3) . ? C5 C6 1.358(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 N5 Cd1 N5 180.00(3) 3_655 . ? N5 Cd1 N3 88.64(7) 3_655 3_655 ? N5 Cd1 N3 91.36(7) . 3_655 ? N5 Cd1 N3 91.36(7) 3_655 . ? N5 Cd1 N3 88.64(7) . . ? N3 Cd1 N3 180.00(9) 3_655 . ? N5 Cd1 Cl1 90.06(6) 3_655 3_655 ? N5 Cd1 Cl1 89.94(6) . 3_655 ? N3 Cd1 Cl1 88.35(5) 3_655 3_655 ? N3 Cd1 Cl1 91.65(5) . 3_655 ? N5 Cd1 Cl1 89.94(6) 3_655 . ? N5 Cd1 Cl1 90.06(6) . . ? N3 Cd1 Cl1 91.65(5) 3_655 . ? N3 Cd1 Cl1 88.35(5) . . ? Cl1 Cd1 Cl1 180.00(2) 3_655 . ? C3 N1 C2 109.44(18) . . ? C3 N2 C1 109.47(18) . . ? C4 N3 C6 105.34(17) . . ? C4 N3 Cd1 135.97(13) . . ? C6 N3 Cd1 116.11(13) . . ? C4 N4 C5 107.80(17) . . ? C7 N5 Cd1 166.42(19) . . ? C2 C1 N2 107.1(2) . . ? C1 C2 N1 106.8(2) . . ? N2 C3 N1 107.18(18) . . ? N2 C3 C4 125.60(18) . . ? N1 C3 C4 127.12(18) . . ? N3 C4 N4 110.99(17) . . ? N3 C4 C3 125.31(18) . . ? N4 C4 C3 123.55(18) . . ? C6 C5 N4 106.04(19) . . ? C5 C6 N3 109.82(19) . . ? N5 C7 S1 178.3(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.676 _refine_diff_density_min -0.550 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 966914' ####################################################################### # # 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 'C8 H12 Cd N6 S4' _chemical_formula_weight 432.88 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 6.1287(4) _cell_length_b 10.5689(7) _cell_length_c 11.8829(7) _cell_angle_alpha 90.00 _cell_angle_beta 98.756(4) _cell_angle_gamma 90.00 _cell_volume 760.73(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 795 _cell_measurement_theta_min 2.5929 _cell_measurement_theta_max 24.9431 _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 1.890 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 1.978 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.789 _exptl_absorpt_correction_T_max 0.821 _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 3948 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 24.96 _reflns_number_total 1286 _reflns_number_gt 1209 _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 '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^)+(0.0418P)^2^+0.3083P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1286 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0321 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0710 _refine_ls_wR_factor_gt 0.0700 _refine_ls_goodness_of_fit_ref 1.193 _refine_ls_restrained_S_all 1.193 _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 0.0000 0.02610(15) Uani 1 2 d S . . S1 S -0.07435(14) 0.20320(7) -0.13737(6) 0.0363(2) Uani 1 1 d . . . S2 S 0.30123(11) 0.14585(7) 0.14193(6) 0.02620(19) Uani 1 1 d . . . N1 N -0.0539(4) 0.0988(3) -0.3525(2) 0.0363(6) Uani 1 1 d . . . N2 N 0.7160(4) 0.0704(3) 0.0926(2) 0.0343(6) Uani 1 1 d . . . N3 N 0.3072(4) 0.4279(2) 0.0099(2) 0.0263(5) Uani 1 1 d . . . H31 H 0.2401 0.3632 0.0400 0.080 Uiso 1 1 calc R . . H30 H 0.2044 0.4695 -0.0384 0.080 Uiso 1 1 calc R . . C1 C -0.0612(4) 0.1408(3) -0.2633(2) 0.0272(6) Uani 1 1 d . . . C2 C 0.5433(4) 0.0994(2) 0.1113(2) 0.0230(5) Uani 1 1 d . . . C3 C 0.4791(5) 0.3768(3) -0.0545(2) 0.0285(6) Uani 1 1 d . . . H3B H 0.4105 0.3222 -0.1154 0.034 Uiso 1 1 calc R . . H3C H 0.5852 0.3270 -0.0040 0.034 Uiso 1 1 calc R . . C4 C 0.4048(5) 0.5158(3) 0.1034(3) 0.0279(6) Uani 1 1 d . . . H4A H 0.5087 0.4700 0.1585 0.033 Uiso 1 1 calc R . . H4B H 0.2888 0.5489 0.1423 0.033 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 0.0215(2) 0.0284(2) 0.0299(2) 0.00266(11) 0.00871(13) 0.00376(10) S1 0.0552(5) 0.0253(4) 0.0294(4) -0.0003(3) 0.0093(3) 0.0073(3) S2 0.0230(3) 0.0282(4) 0.0286(3) -0.0015(3) 0.0076(3) 0.0039(3) N1 0.0302(13) 0.0456(15) 0.0341(14) -0.0087(12) 0.0080(10) -0.0043(11) N2 0.0268(13) 0.0416(15) 0.0354(13) -0.0040(11) 0.0076(10) 0.0010(11) N3 0.0235(11) 0.0269(12) 0.0294(11) 0.0023(10) 0.0071(9) -0.0029(9) C1 0.0208(12) 0.0280(14) 0.0326(15) 0.0028(12) 0.0039(11) -0.0014(11) C2 0.0261(14) 0.0218(13) 0.0214(12) -0.0010(10) 0.0050(10) -0.0009(11) C3 0.0333(14) 0.0236(13) 0.0300(14) -0.0018(11) 0.0097(11) -0.0013(11) C4 0.0312(16) 0.0278(14) 0.0262(14) -0.0011(11) 0.0093(12) -0.0010(11) _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 2.319(2) 1_455 ? Cd1 N2 2.319(2) 3_655 ? Cd1 S1 2.6941(8) 3 ? Cd1 S1 2.6941(8) . ? Cd1 S2 2.7715(7) . ? Cd1 S2 2.7715(7) 3 ? S1 C1 1.649(3) . ? S2 C2 1.655(3) . ? N1 C1 1.156(4) . ? N2 C2 1.156(4) . ? N2 Cd1 2.319(2) 1_655 ? N3 C3 1.494(4) . ? N3 C4 1.502(4) . ? C3 C4 1.502(4) 3_665 ? C4 C3 1.502(4) 3_665 ? 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) 1_455 3_655 ? N2 Cd1 S1 92.18(7) 1_455 3 ? N2 Cd1 S1 87.82(7) 3_655 3 ? N2 Cd1 S1 87.82(7) 1_455 . ? N2 Cd1 S1 92.18(7) 3_655 . ? S1 Cd1 S1 180.00(3) 3 . ? N2 Cd1 S2 90.65(6) 1_455 . ? N2 Cd1 S2 89.35(6) 3_655 . ? S1 Cd1 S2 92.24(2) 3 . ? S1 Cd1 S2 87.76(2) . . ? N2 Cd1 S2 89.35(6) 1_455 3 ? N2 Cd1 S2 90.65(6) 3_655 3 ? S1 Cd1 S2 87.76(2) 3 3 ? S1 Cd1 S2 92.24(2) . 3 ? S2 Cd1 S2 180.00(3) . 3 ? C1 S1 Cd1 101.77(10) . . ? C2 S2 Cd1 103.74(9) . . ? C2 N2 Cd1 162.2(2) . 1_655 ? C3 N3 C4 111.7(2) . . ? N1 C1 S1 178.8(3) . . ? N2 C2 S2 177.4(3) . . ? N3 C3 C4 109.7(2) . 3_665 ? N3 C4 C3 109.9(2) . 3_665 ? 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 H30 N1 0.90 2.01 2.879(3) 162.3 2_554 N3 H31 N1 0.90 2.40 2.959(3) 120.7 4_566 _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.497 _refine_diff_density_min -1.646 _refine_diff_density_rms 0.137 _database_code_depnum_ccdc_archive 'CCDC 966915' ####################################################################### # # 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 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H4 Cd N6 O2' _chemical_formula_weight 280.53 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' O O 0.0106 0.0060 '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 6.6354(13) _cell_length_b 8.6178(17) _cell_length_c 6.8749(14) _cell_angle_alpha 90.00 _cell_angle_beta 95.16(3) _cell_angle_gamma 90.00 _cell_volume 391.53(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13712 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 27.455 _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 2.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 2.764 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.705 _exptl_absorpt_correction_T_max 0.759 _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 3706 _diffrn_reflns_av_R_equivalents 0.0148 _diffrn_reflns_av_sigmaI/netI 0.0116 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.80 _diffrn_reflns_theta_max 27.43 _reflns_number_total 887 _reflns_number_gt 848 _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 '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^)+(0.0500P)^2^+1.5264P] 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 887 _refine_ls_number_parameters 65 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0284 _refine_ls_wR_factor_ref 0.0858 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _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 -0.5000 -0.5000 0.01319(17) Uani 1 2 d S . . N1 N 0.7518(5) -0.3551(4) -0.6759(6) 0.0283(8) Uani 1 1 d . . . N2 N 0.2629(4) -0.3552(3) -0.5926(4) 0.0110(5) Uani 1 1 d . . . H2A H 0.3781 -0.3986 -0.5621 0.013 Uiso 1 1 calc R . . N3 N 0.4601(5) -0.1807(4) -0.7437(5) 0.0210(7) Uani 1 1 d . . . C1 C 0.6113(5) -0.2759(5) -0.7025(6) 0.0199(7) Uani 1 1 d . . . C2 C 0.2799(5) -0.2271(4) -0.6774(5) 0.0168(7) Uani 1 1 d . . . OH1 O 0.1250(5) -0.1297(4) -0.7087(6) 0.0453(9) Uani 1 1 d . . . H0 H -0.022(9) -0.160(7) -0.670(8) 0.043(16) 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 0.0100(2) 0.0118(2) 0.0181(2) -0.00011(10) 0.00332(15) 0.00016(10) N1 0.0176(16) 0.0316(19) 0.0357(19) 0.0145(15) 0.0027(14) 0.0055(14) N2 0.0047(11) 0.0080(12) 0.0212(14) 0.0051(11) 0.0061(10) -0.0005(10) N3 0.0136(15) 0.0212(15) 0.0290(17) 0.0116(13) 0.0061(12) 0.0020(12) C1 0.0154(17) 0.0217(18) 0.0229(17) 0.0075(14) 0.0026(13) -0.0034(14) C2 0.0139(16) 0.0167(16) 0.0205(17) 0.0005(13) 0.0049(13) -0.0015(13) OH1 0.0276(17) 0.039(2) 0.071(3) 0.0190(18) 0.0168(17) 0.0068(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 N2 2.281(3) . ? Cd1 N2 2.281(3) 3_544 ? Cd1 N1 2.319(3) 3_644 ? Cd1 N1 2.319(3) 1_455 ? Cd1 N3 2.384(3) 4_556 ? Cd1 N3 2.384(3) 2_543 ? N1 C1 1.156(5) . ? N1 Cd1 2.319(3) 1_655 ? N2 C2 1.258(4) . ? N3 C1 1.308(5) . ? N3 C2 1.376(4) . ? N3 Cd1 2.384(3) 2_553 ? C2 OH1 1.330(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 N2 Cd1 N2 180.00(11) . 3_544 ? N2 Cd1 N1 85.12(11) . 3_644 ? N2 Cd1 N1 94.88(11) 3_544 3_644 ? N2 Cd1 N1 94.88(11) . 1_455 ? N2 Cd1 N1 85.12(11) 3_544 1_455 ? N1 Cd1 N1 180.000(1) 3_644 1_455 ? N2 Cd1 N3 89.29(11) . 4_556 ? N2 Cd1 N3 90.71(11) 3_544 4_556 ? N1 Cd1 N3 95.00(13) 3_644 4_556 ? N1 Cd1 N3 85.00(13) 1_455 4_556 ? N2 Cd1 N3 90.71(11) . 2_543 ? N2 Cd1 N3 89.29(11) 3_544 2_543 ? N1 Cd1 N3 85.00(13) 3_644 2_543 ? N1 Cd1 N3 95.00(13) 1_455 2_543 ? N3 Cd1 N3 180.000(1) 4_556 2_543 ? C1 N1 Cd1 157.7(3) . 1_655 ? C2 N2 Cd1 135.4(2) . . ? C1 N3 C2 114.7(3) . . ? C1 N3 Cd1 115.8(2) . 2_553 ? C2 N3 Cd1 126.3(2) . 2_553 ? N1 C1 N3 175.3(4) . . ? N2 C2 OH1 121.9(3) . . ? N2 C2 N3 121.7(3) . . ? OH1 C2 N3 116.4(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.833 _refine_diff_density_min -1.050 _refine_diff_density_rms 0.185 _database_code_depnum_ccdc_archive 'CCDC 966916'