# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_111205a #TrackingRef '111205a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 Cd N4 O6 S' _chemical_formula_weight 534.86 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' _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 12.5331(4) _cell_length_b 13.4857(5) _cell_length_c 12.0851(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.3040(10) _cell_angle_gamma 90.00 _cell_volume 1950.15(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1961 _cell_measurement_theta_min 3.0150 _cell_measurement_theta_max 28.3499 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.822 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 1.273 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.77423 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3173 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_unetI/netI 0.0228 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1719 _reflns_number_gt 1581 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'publCIF (Westrip, 2010)' _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^)+(0.0414P)^2^+1.0697P] 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 1719 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0260 _refine_ls_R_factor_gt 0.0238 _refine_ls_wR_factor_ref 0.0666 _refine_ls_wR_factor_gt 0.0645 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 0.02252(12) Uani 1 2 d S . . N1 N 0.08852(17) 0.37746(14) 0.42531(16) 0.0277(4) Uani 1 1 d . . . N2 N 0.28826(16) 0.36456(14) 0.25568(15) 0.0271(4) Uani 1 1 d . . . H2B H 0.3448 0.3206 0.2705 0.033 Uiso 1 1 d R . . O1 O -0.05111(15) 0.57979(13) 0.32029(13) 0.0324(4) Uani 1 1 d . . . O2 O -0.08768(16) 0.70511(12) 0.17292(14) 0.0373(4) Uani 1 1 d . . . O3 O -0.15656(14) 0.40184(13) 0.47323(14) 0.0351(4) Uani 1 1 d . . . H3B H -0.1432 0.3513 0.5172 0.042 Uiso 1 1 d R . . H3C H -0.1833 0.3836 0.4031 0.042 Uiso 1 1 d R . . S1 S 0.0000 0.64218(6) 0.2500 0.02284(19) Uani 1 2 d S . . C1 C 0.16197(19) 0.40360(16) 0.36907(18) 0.0264(5) Uani 1 1 d . . . H1 H 0.1763 0.4707 0.3627 0.032 Uiso 1 1 calc R . . C2 C 0.21733(19) 0.33563(17) 0.32013(18) 0.0236(5) Uani 1 1 d . . . C3 C 0.1963(2) 0.23509(17) 0.3328(2) 0.0321(5) Uani 1 1 d . . . H3 H 0.2328 0.1867 0.3027 0.039 Uiso 1 1 calc R . . C4 C 0.1210(2) 0.20861(18) 0.3901(2) 0.0377(6) Uani 1 1 d . . . H4 H 0.1055 0.1421 0.3984 0.045 Uiso 1 1 calc R . . C5 C 0.0685(2) 0.28112(18) 0.4352(2) 0.0339(6) Uani 1 1 d . . . H5 H 0.0175 0.2624 0.4737 0.041 Uiso 1 1 calc R . . C6 C 0.3382(2) 0.46411(19) 0.2737(2) 0.0302(5) Uani 1 1 d . . . H6A H 0.2785 0.5124 0.2616 0.036 Uiso 1 1 calc R . . H6B H 0.3756 0.4757 0.2152 0.036 Uiso 1 1 calc R . . C7 C 0.4205(2) 0.48211(18) 0.3909(2) 0.0276(5) Uani 1 1 d . . . C8 C 0.5131(2) 0.42051(17) 0.4330(2) 0.0304(5) Uani 1 1 d . . . H8 H 0.5228 0.3668 0.3886 0.036 Uiso 1 1 calc R . . C9 C 0.4088(2) 0.56214(17) 0.4599(2) 0.0301(5) Uani 1 1 d . . . H9 H 0.3479 0.6045 0.4338 0.036 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 0.02718(17) 0.02065(17) 0.02271(17) 0.00173(7) 0.01201(12) 0.00113(8) N1 0.0312(11) 0.0244(10) 0.0306(10) 0.0022(8) 0.0141(8) 0.0030(9) N2 0.0314(10) 0.0250(10) 0.0277(10) -0.0020(8) 0.0129(8) 0.0034(8) O1 0.0389(9) 0.0336(9) 0.0240(8) 0.0068(7) 0.0081(7) -0.0066(8) O2 0.0557(12) 0.0281(9) 0.0291(9) 0.0056(7) 0.0142(8) 0.0156(9) O3 0.0367(10) 0.0368(10) 0.0281(9) 0.0017(7) 0.0041(7) -0.0076(8) S1 0.0356(4) 0.0172(4) 0.0175(4) 0.000 0.0105(3) 0.000 C1 0.0352(13) 0.0173(11) 0.0292(12) 0.0036(9) 0.0133(10) 0.0032(10) C2 0.0251(11) 0.0250(12) 0.0199(10) 0.0006(9) 0.0054(9) 0.0010(9) C3 0.0397(14) 0.0208(12) 0.0370(13) -0.0080(10) 0.0132(11) 0.0014(11) C4 0.0461(15) 0.0206(12) 0.0513(15) 0.0002(11) 0.0220(13) -0.0049(12) C5 0.0399(14) 0.0237(13) 0.0433(14) 0.0027(10) 0.0204(12) -0.0014(11) C6 0.0398(14) 0.0254(12) 0.0317(12) 0.0024(11) 0.0201(11) -0.0006(12) C7 0.0332(14) 0.0230(11) 0.0339(14) 0.0011(10) 0.0212(12) -0.0051(11) C8 0.0388(13) 0.0207(12) 0.0394(13) -0.0033(10) 0.0236(11) -0.0026(11) C9 0.0337(13) 0.0227(12) 0.0385(13) 0.0011(10) 0.0181(11) -0.0002(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 O3 2.3085(17) 5_566 ? Cd1 O3 2.3085(17) . ? Cd1 N1 2.3178(19) 5_566 ? Cd1 N1 2.3178(19) . ? Cd1 O1 2.3361(15) . ? Cd1 O1 2.3361(15) 5_566 ? N1 C5 1.335(3) . ? N1 C1 1.344(3) . ? N2 C2 1.400(3) . ? N2 C6 1.470(3) . ? N2 H2B 0.9000 . ? O1 S1 1.4709(16) . ? O2 S1 1.4787(17) . ? O3 H3B 0.8501 . ? O3 H3C 0.8499 . ? S1 O1 1.4709(16) 2 ? S1 O2 1.4787(17) 2 ? C1 C2 1.384(3) . ? C1 H1 0.9300 . ? C2 C3 1.398(3) . ? C3 C4 1.373(3) . ? C3 H3 0.9300 . ? C4 C5 1.378(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.503(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.394(4) . ? C7 C9 1.398(3) . ? C8 C9 1.391(3) 5_666 ? C8 H8 0.9300 . ? C9 C8 1.391(3) 5_666 ? C9 H9 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 O3 Cd1 O3 180.00(8) 5_566 . ? O3 Cd1 N1 91.26(7) 5_566 5_566 ? O3 Cd1 N1 88.74(7) . 5_566 ? O3 Cd1 N1 88.74(7) 5_566 . ? O3 Cd1 N1 91.26(7) . . ? N1 Cd1 N1 180.00(8) 5_566 . ? O3 Cd1 O1 81.53(6) 5_566 . ? O3 Cd1 O1 98.47(6) . . ? N1 Cd1 O1 90.17(6) 5_566 . ? N1 Cd1 O1 89.83(6) . . ? O3 Cd1 O1 98.47(6) 5_566 5_566 ? O3 Cd1 O1 81.53(6) . 5_566 ? N1 Cd1 O1 89.83(6) 5_566 5_566 ? N1 Cd1 O1 90.17(6) . 5_566 ? O1 Cd1 O1 180.00(4) . 5_566 ? C5 N1 C1 118.4(2) . . ? C5 N1 Cd1 122.31(15) . . ? C1 N1 Cd1 119.29(15) . . ? C2 N2 C6 119.00(18) . . ? C2 N2 H2B 107.3 . . ? C6 N2 H2B 107.3 . . ? S1 O1 Cd1 138.96(10) . . ? Cd1 O3 H3B 111.8 . . ? Cd1 O3 H3C 111.9 . . ? H3B O3 H3C 109.7 . . ? O1 S1 O1 110.22(14) 2 . ? O1 S1 O2 108.81(10) 2 2 ? O1 S1 O2 109.52(9) . 2 ? O1 S1 O2 109.52(9) 2 . ? O1 S1 O2 108.81(10) . . ? O2 S1 O2 109.95(15) 2 . ? N1 C1 C2 123.3(2) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C1 C2 C3 117.4(2) . . ? C1 C2 N2 122.3(2) . . ? C3 C2 N2 120.2(2) . . ? C4 C3 C2 119.2(2) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 119.7(2) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? N1 C5 C4 122.0(2) . . ? N1 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? N2 C6 C7 115.46(19) . . ? N2 C6 H6A 108.4 . . ? C7 C6 H6A 108.4 . . ? N2 C6 H6B 108.4 . . ? C7 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? C8 C7 C9 117.8(3) . . ? C8 C7 C6 120.7(2) . . ? C9 C7 C6 121.5(2) . . ? C9 C8 C7 121.2(2) 5_666 . ? C9 C8 H8 119.4 5_666 . ? C7 C8 H8 119.4 . . ? C8 C9 C7 121.0(2) 5_666 . ? C8 C9 H9 119.5 5_666 . ? C7 C9 H9 119.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.498 _refine_diff_density_min -0.837 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 933891' ####################################################################### # # 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_111227c #TrackingRef '111205a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H22 Cd N4 O4' _chemical_formula_weight 566.88 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' O O 0.0106 0.0060 '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 10.0900(10) _cell_length_b 10.2601(11) _cell_length_c 12.6419(13) _cell_angle_alpha 87.932(2) _cell_angle_beta 73.1320(10) _cell_angle_gamma 64.7300(10) _cell_volume 1126.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3253 _cell_measurement_theta_min 2.4215 _cell_measurement_theta_max 27.476 _exptl_crystal_description lamellate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 1.012 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.77 _exptl_absorpt_correction_T_max 0.85 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5768 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_unetI/netI 0.0449 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3915 _reflns_number_gt 3398 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'publCIF (Westrip, 2010)' _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^)+(0.0468P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3915 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0826 _refine_ls_wR_factor_gt 0.0789 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.87827(3) 0.56378(3) 0.363532(19) 0.02914(10) Uani 1 1 d . . . O1 O 0.8454(3) 0.4904(2) 0.54245(18) 0.0312(5) Uani 1 1 d . . . N1 N 0.8932(3) 0.6637(3) 0.1909(2) 0.0318(6) Uani 1 1 d . . . O2 O 0.8636(3) 0.5693(3) 0.69541(19) 0.0345(6) Uani 1 1 d . . . C2 C 0.2737(4) 0.5825(4) 0.6758(3) 0.0330(8) Uani 1 1 d . . . O3 O 0.3422(3) 0.4535(3) 0.6361(2) 0.0400(6) Uani 1 1 d . . . O4 O 0.1299(3) 0.6543(3) 0.7014(2) 0.0403(6) Uani 1 1 d . . . C4 C 0.5257(4) 0.5886(4) 0.6511(3) 0.0266(7) Uani 1 1 d . . . H4 H 0.5722 0.5059 0.6013 0.032 Uiso 1 1 calc R . . C15 C 0.5338(4) 0.6894(4) 0.0519(3) 0.0313(8) Uani 1 1 d . . . C6 C 0.2998(4) 0.7803(4) 0.7677(3) 0.0344(8) Uani 1 1 d . . . H6 H 0.1935 0.8255 0.7991 0.041 Uiso 1 1 calc R . . C3 C 0.6160(4) 0.6452(4) 0.6779(3) 0.0257(7) Uani 1 1 d . . . C1 C 0.7879(4) 0.5628(3) 0.6340(3) 0.0263(7) Uani 1 1 d . . . N4 N 0.1888(3) 1.2090(3) 0.5585(2) 0.0336(7) Uani 1 1 d . . . C5 C 0.3678(4) 0.6535(4) 0.6975(3) 0.0283(7) Uani 1 1 d . . . C9 C 0.8279(4) 0.6460(4) 0.1187(3) 0.0312(8) Uani 1 1 d . . . H9 H 0.7597 0.6044 0.1413 0.037 Uiso 1 1 calc R . . C10 C 0.8559(4) 0.6863(4) 0.0111(3) 0.0334(8) Uani 1 1 d . . . N2 N 0.7889(4) 0.6664(3) -0.0620(2) 0.0417(8) Uani 1 1 d . . . H2 H 0.8087 0.6949 -0.1271 0.050 Uiso 1 1 calc R . . C23 C 0.1258(4) 1.1971(4) 0.4828(3) 0.0316(8) Uani 1 1 d . . . H23 H 0.0511 1.2810 0.4675 0.038 Uiso 1 1 calc R . . N3 N 0.0924(4) 1.0708(3) 0.3485(3) 0.0439(8) Uani 1 1 d . . . H3 H 0.0385 1.1533 0.3293 0.053 Uiso 1 1 calc R . . C8 C 0.5456(4) 0.7708(4) 0.7495(3) 0.0339(8) Uani 1 1 d . . . H8 H 0.6051 0.8085 0.7692 0.041 Uiso 1 1 calc R . . C22 C 0.1647(4) 1.0673(4) 0.4254(3) 0.0321(8) Uani 1 1 d . . . C16 C 0.4616(4) 0.6246(4) 0.1286(3) 0.0356(8) Uani 1 1 d . . . H16 H 0.5058 0.5242 0.1273 0.043 Uiso 1 1 calc R . . C17 C 0.3240(4) 0.7068(4) 0.2078(3) 0.0368(8) Uani 1 1 d . . . H17 H 0.2772 0.6609 0.2599 0.044 Uiso 1 1 calc R . . C18 C 0.2546(4) 0.8548(4) 0.2115(3) 0.0324(8) Uani 1 1 d . . . C14 C 0.6864(4) 0.5994(4) -0.0335(3) 0.0386(9) Uani 1 1 d . . . H14A H 0.7364 0.5077 -0.0053 0.046 Uiso 1 1 calc R . . H14B H 0.6673 0.5785 -0.1005 0.046 Uiso 1 1 calc R . . C11 C 0.9561(4) 0.7512(4) -0.0190(3) 0.0423(9) Uani 1 1 d . . . H11 H 0.9786 0.7806 -0.0898 0.051 Uiso 1 1 calc R . . C12 C 1.0214(5) 0.7713(4) 0.0568(3) 0.0456(10) Uani 1 1 d . . . H12 H 1.0880 0.8148 0.0378 0.055 Uiso 1 1 calc R . . C20 C 0.4654(5) 0.8375(4) 0.0547(3) 0.0440(10) Uani 1 1 d . . . H20 H 0.5129 0.8831 0.0029 0.053 Uiso 1 1 calc R . . C19 C 0.3267(5) 0.9197(4) 0.1334(3) 0.0432(9) Uani 1 1 d . . . H19 H 0.2815 1.0200 0.1338 0.052 Uiso 1 1 calc R . . C24 C 0.2948(4) 1.0878(4) 0.5811(3) 0.0426(9) Uani 1 1 d . . . H24 H 0.3401 1.0939 0.6340 0.051 Uiso 1 1 calc R . . C7 C 0.3883(4) 0.8399(4) 0.7914(3) 0.0407(9) Uani 1 1 d . . . H7 H 0.3413 0.9274 0.8359 0.049 Uiso 1 1 calc R . . C21 C 0.1030(4) 0.9422(4) 0.2985(3) 0.0416(9) Uani 1 1 d . . . H21A H 0.0212 0.9694 0.2647 0.050 Uiso 1 1 calc R . . H21B H 0.0861 0.8813 0.3564 0.050 Uiso 1 1 calc R . . C25 C 0.3381(5) 0.9563(4) 0.5291(3) 0.0434(9) Uani 1 1 d . . . H25 H 0.4116 0.8742 0.5474 0.052 Uiso 1 1 calc R . . C13 C 0.9876(4) 0.7266(4) 0.1603(3) 0.0427(9) Uani 1 1 d . . . H13 H 1.0321 0.7408 0.2110 0.051 Uiso 1 1 calc R . . C26 C 0.2755(4) 0.9425(4) 0.4502(3) 0.0408(9) Uani 1 1 d . . . H26 H 0.3060 0.8523 0.4141 0.049 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 0.02683(15) 0.03716(17) 0.02780(15) 0.00077(10) -0.00876(10) -0.01741(12) O1 0.0258(12) 0.0364(13) 0.0283(13) 0.0007(10) -0.0055(10) -0.0125(11) N1 0.0341(16) 0.0387(17) 0.0277(15) 0.0049(12) -0.0114(12) -0.0192(14) O2 0.0225(12) 0.0536(16) 0.0318(13) 0.0040(11) -0.0119(10) -0.0182(12) C2 0.031(2) 0.054(2) 0.0274(19) 0.0125(16) -0.0147(15) -0.0275(18) O3 0.0337(14) 0.0468(16) 0.0489(16) -0.0020(12) -0.0144(12) -0.0244(13) O4 0.0241(13) 0.0502(16) 0.0531(16) 0.0073(12) -0.0160(11) -0.0195(12) C4 0.0262(17) 0.0333(18) 0.0246(17) 0.0037(13) -0.0102(13) -0.0152(15) C15 0.036(2) 0.0324(19) 0.0303(19) 0.0018(14) -0.0164(15) -0.0156(16) C6 0.0213(17) 0.047(2) 0.0306(19) 0.0007(15) -0.0052(14) -0.0122(16) C3 0.0228(17) 0.0347(19) 0.0242(17) 0.0053(13) -0.0100(13) -0.0149(15) C1 0.0231(17) 0.0307(18) 0.0315(19) 0.0099(14) -0.0096(14) -0.0174(15) N4 0.0350(17) 0.0357(17) 0.0317(16) 0.0034(12) -0.0098(13) -0.0170(14) C5 0.0265(18) 0.040(2) 0.0257(17) 0.0064(14) -0.0115(14) -0.0190(16) C9 0.0320(19) 0.0337(19) 0.0298(19) 0.0047(14) -0.0073(15) -0.0176(16) C10 0.0277(18) 0.035(2) 0.0289(19) -0.0037(14) -0.0045(14) -0.0080(16) N2 0.0420(19) 0.061(2) 0.0228(16) 0.0033(14) -0.0081(13) -0.0243(17) C23 0.0310(19) 0.0325(19) 0.0304(19) 0.0042(14) -0.0057(15) -0.0156(16) N3 0.045(2) 0.0337(18) 0.049(2) -0.0075(14) -0.0218(16) -0.0087(15) C8 0.0298(19) 0.041(2) 0.037(2) -0.0002(16) -0.0133(15) -0.0194(17) C22 0.0269(18) 0.036(2) 0.0312(19) 0.0009(14) -0.0049(14) -0.0139(16) C16 0.038(2) 0.0279(19) 0.043(2) 0.0032(15) -0.0155(17) -0.0147(17) C17 0.038(2) 0.036(2) 0.042(2) 0.0082(16) -0.0144(17) -0.0212(17) C18 0.0325(19) 0.0327(19) 0.038(2) -0.0008(15) -0.0161(15) -0.0152(16) C14 0.041(2) 0.043(2) 0.032(2) -0.0047(16) -0.0135(16) -0.0166(18) C11 0.037(2) 0.052(2) 0.035(2) 0.0123(17) -0.0055(16) -0.0207(19) C12 0.042(2) 0.052(2) 0.050(2) 0.0080(18) -0.0092(19) -0.030(2) C20 0.052(2) 0.037(2) 0.043(2) 0.0078(16) -0.0092(18) -0.023(2) C19 0.051(2) 0.0242(19) 0.048(2) 0.0025(16) -0.0129(19) -0.0123(18) C24 0.041(2) 0.047(2) 0.041(2) 0.0042(17) -0.0167(17) -0.0173(19) C7 0.034(2) 0.045(2) 0.040(2) -0.0080(17) -0.0112(17) -0.0140(18) C21 0.036(2) 0.040(2) 0.049(2) -0.0069(17) -0.0146(17) -0.0142(18) C25 0.044(2) 0.040(2) 0.040(2) 0.0075(17) -0.0157(18) -0.0112(19) C13 0.042(2) 0.052(2) 0.042(2) 0.0021(18) -0.0152(18) -0.026(2) C26 0.043(2) 0.032(2) 0.043(2) -0.0023(16) -0.0105(18) -0.0128(18) _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 O2 2.261(2) 2_766 ? Cd1 N4 2.302(3) 2_676 ? Cd1 O3 2.304(2) 2_666 ? Cd1 O1 2.334(2) . ? Cd1 N1 2.370(3) . ? Cd1 O4 2.453(3) 2_666 ? Cd1 C2 2.704(3) 2_666 ? O1 C1 1.238(4) . ? N1 C9 1.329(4) . ? N1 C13 1.329(4) . ? O2 C1 1.258(4) . ? O2 Cd1 2.261(2) 2_766 ? C2 O3 1.244(4) . ? C2 O4 1.259(4) . ? C2 C5 1.504(4) . ? C2 Cd1 2.704(3) 2_666 ? O3 Cd1 2.304(2) 2_666 ? O4 Cd1 2.453(3) 2_666 ? C4 C5 1.380(4) . ? C4 C3 1.389(4) . ? C4 H4 0.9300 . ? C15 C16 1.368(5) . ? C15 C20 1.371(5) . ? C15 C14 1.511(5) . ? C6 C7 1.378(5) . ? C6 C5 1.385(5) . ? C6 H6 0.9300 . ? C3 C8 1.383(5) . ? C3 C1 1.501(4) . ? N4 C23 1.327(4) . ? N4 C24 1.337(5) . ? N4 Cd1 2.302(3) 2_676 ? C9 C10 1.392(5) . ? C9 H9 0.9300 . ? C10 N2 1.358(4) . ? C10 C11 1.393(5) . ? N2 C14 1.431(5) . ? N2 H2 0.8600 . ? C23 C22 1.383(5) . ? C23 H23 0.9300 . ? N3 C22 1.366(5) . ? N3 C21 1.432(4) . ? N3 H3 0.8600 . ? C8 C7 1.371(5) . ? C8 H8 0.9300 . ? C22 C26 1.393(5) . ? C16 C17 1.377(5) . ? C16 H16 0.9300 . ? C17 C18 1.370(5) . ? C17 H17 0.9300 . ? C18 C19 1.376(5) . ? C18 C21 1.509(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C11 C12 1.376(5) . ? C11 H11 0.9300 . ? C12 C13 1.366(5) . ? C12 H12 0.9300 . ? C20 C19 1.380(5) . ? C20 H20 0.9300 . ? C19 H19 0.9300 . ? C24 C25 1.356(5) . ? C24 H24 0.9300 . ? C7 H7 0.9300 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C25 C26 1.366(5) . ? C25 H25 0.9300 . ? C13 H13 0.9300 . ? C26 H26 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 O2 Cd1 N4 111.57(9) 2_766 2_676 ? O2 Cd1 O3 139.57(9) 2_766 2_666 ? N4 Cd1 O3 108.80(10) 2_676 2_666 ? O2 Cd1 O1 95.16(8) 2_766 . ? N4 Cd1 O1 87.74(9) 2_676 . ? O3 Cd1 O1 88.45(9) 2_666 . ? O2 Cd1 N1 89.25(9) 2_766 . ? N4 Cd1 N1 86.69(10) 2_676 . ? O3 Cd1 N1 90.93(9) 2_666 . ? O1 Cd1 N1 173.88(8) . . ? O2 Cd1 O4 84.72(8) 2_766 2_666 ? N4 Cd1 O4 163.64(9) 2_676 2_666 ? O3 Cd1 O4 55.01(8) 2_666 2_666 ? O1 Cd1 O4 89.37(8) . 2_666 ? N1 Cd1 O4 95.27(9) . 2_666 ? O2 Cd1 C2 112.39(10) 2_766 2_666 ? N4 Cd1 C2 136.04(11) 2_676 2_666 ? O3 Cd1 C2 27.29(9) 2_666 2_666 ? O1 Cd1 C2 88.62(9) . 2_666 ? N1 Cd1 C2 93.62(10) . 2_666 ? O4 Cd1 C2 27.72(10) 2_666 2_666 ? C1 O1 Cd1 130.3(2) . . ? C9 N1 C13 118.6(3) . . ? C9 N1 Cd1 124.1(2) . . ? C13 N1 Cd1 116.9(2) . . ? C1 O2 Cd1 117.9(2) . 2_766 ? O3 C2 O4 123.1(3) . . ? O3 C2 C5 118.0(3) . . ? O4 C2 C5 118.9(3) . . ? O3 C2 Cd1 58.14(17) . 2_666 ? O4 C2 Cd1 64.98(18) . 2_666 ? C5 C2 Cd1 175.9(3) . 2_666 ? C2 O3 Cd1 94.6(2) . 2_666 ? C2 O4 Cd1 87.3(2) . 2_666 ? C5 C4 C3 120.9(3) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.6 . . ? C16 C15 C20 118.6(3) . . ? C16 C15 C14 120.5(3) . . ? C20 C15 C14 120.9(3) . . ? C7 C6 C5 120.6(3) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C8 C3 C4 119.2(3) . . ? C8 C3 C1 121.9(3) . . ? C4 C3 C1 118.8(3) . . ? O1 C1 O2 124.4(3) . . ? O1 C1 C3 118.7(3) . . ? O2 C1 C3 116.9(3) . . ? C23 N4 C24 117.8(3) . . ? C23 N4 Cd1 118.8(2) . 2_676 ? C24 N4 Cd1 123.2(2) . 2_676 ? C4 C5 C6 118.8(3) . . ? C4 C5 C2 119.9(3) . . ? C6 C5 C2 121.2(3) . . ? N1 C9 C10 123.6(3) . . ? N1 C9 H9 118.2 . . ? C10 C9 H9 118.2 . . ? N2 C10 C9 122.8(3) . . ? N2 C10 C11 120.6(3) . . ? C9 C10 C11 116.6(3) . . ? C10 N2 C14 121.8(3) . . ? C10 N2 H2 119.1 . . ? C14 N2 H2 119.1 . . ? N4 C23 C22 123.8(3) . . ? N4 C23 H23 118.1 . . ? C22 C23 H23 118.1 . . ? C22 N3 C21 122.5(3) . . ? C22 N3 H3 118.7 . . ? C21 N3 H3 118.7 . . ? C7 C8 C3 120.2(3) . . ? C7 C8 H8 119.9 . . ? C3 C8 H8 119.9 . . ? N3 C22 C23 117.8(3) . . ? N3 C22 C26 124.8(3) . . ? C23 C22 C26 117.4(3) . . ? C15 C16 C17 120.5(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C18 C17 C16 121.4(3) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C17 C18 C19 118.0(3) . . ? C17 C18 C21 120.2(3) . . ? C19 C18 C21 121.7(3) . . ? N2 C14 C15 114.3(3) . . ? N2 C14 H14A 108.7 . . ? C15 C14 H14A 108.7 . . ? N2 C14 H14B 108.7 . . ? C15 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? C12 C11 C10 119.5(3) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C13 C12 C11 119.4(3) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C15 C20 C19 120.8(3) . . ? C15 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C18 C19 C20 120.7(3) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? N4 C24 C25 121.8(4) . . ? N4 C24 H24 119.1 . . ? C25 C24 H24 119.1 . . ? C8 C7 C6 120.2(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? N3 C21 C18 114.5(3) . . ? N3 C21 H21A 108.6 . . ? C18 C21 H21A 108.6 . . ? N3 C21 H21B 108.6 . . ? C18 C21 H21B 108.6 . . ? H21A C21 H21B 107.6 . . ? C24 C25 C26 121.0(4) . . ? C24 C25 H25 119.5 . . ? C26 C25 H25 119.5 . . ? N1 C13 C12 122.3(4) . . ? N1 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? C25 C26 C22 118.1(3) . . ? C25 C26 H26 120.9 . . ? C22 C26 H26 120.9 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.666 _refine_diff_density_min -0.858 _refine_diff_density_rms 0.081 _database_code_depnum_ccdc_archive 'CCDC 933892' ####################################################################### # # 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_111214g #TrackingRef '111205a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H22 N4 O4 Pb' _chemical_formula_weight 661.67 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' Pb Pb -3.3944 10.1111 '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 7.2970(6) _cell_length_b 15.7569(16) _cell_length_c 10.1351(11) _cell_angle_alpha 90.00 _cell_angle_beta 98.9210(10) _cell_angle_gamma 90.00 _cell_volume 1151.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2930 _cell_measurement_theta_min 2.4080 _cell_measurement_theta_max 24.7105 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.909 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 7.370 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 0.92 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6112 _diffrn_reflns_av_R_equivalents 0.0524 _diffrn_reflns_av_unetI/netI 0.0485 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2116 _reflns_number_gt 1853 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'publCIF (Westrip, 2010)' _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^)+(0.0227P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2116 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0326 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0559 _refine_ls_wR_factor_gt 0.0542 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _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 Pb1 Pb 0.84126(3) 0.2500 0.49387(2) 0.03485(10) Uani 1 2 d S . . N1 N 0.6648(5) -0.0846(3) 0.7130(5) 0.0527(11) Uani 1 1 d . . . H1 H 0.6474 -0.1385 0.7081 0.063 Uiso 1 1 calc R . . N2 N 0.7834(5) 0.0860(3) 0.4973(4) 0.0410(10) Uani 1 1 d . . . O1 O 0.5800(6) 0.2500 0.6065(4) 0.0393(11) Uani 1 2 d S . . O2 O 0.8375(6) 0.2500 0.7507(5) 0.0586(15) Uani 1 2 d S . . O3 O 0.5798(6) 0.2500 1.3129(4) 0.0383(11) Uani 1 2 d S . . O4 O 0.8367(6) 0.2500 1.2252(4) 0.0526(14) Uani 1 2 d S . . C1 C 0.6653(9) 0.2500 0.7235(6) 0.0314(14) Uani 1 2 d S . . C2 C 0.6649(9) 0.2500 1.2130(6) 0.0322(14) Uani 1 2 d S . . C3 C 0.5559(8) 0.2500 0.8378(6) 0.0301(14) Uani 1 2 d S . . C4 C 0.6472(8) 0.2500 0.9675(6) 0.0290(14) Uani 1 2 d S . . H4 H 0.7762 0.2500 0.9821 0.035 Uiso 1 2 calc SR . . C5 C 0.5550(8) 0.2500 1.0765(6) 0.0304(14) Uani 1 2 d S . . C6 C 0.3621(8) 0.2500 1.0528(7) 0.0371(15) Uani 1 2 d S . . H6 H 0.2965 0.2500 1.1245 0.044 Uiso 1 2 calc SR . . C7 C 0.2676(9) 0.2500 0.9247(7) 0.0450(18) Uani 1 2 d S . . H7 H 0.1386 0.2500 0.9103 0.054 Uiso 1 2 calc SR . . C8 C 0.3632(9) 0.2500 0.8167(6) 0.0382(16) Uani 1 2 d S . . H8 H 0.2983 0.2500 0.7301 0.046 Uiso 1 2 calc SR . . C9 C 0.6479(6) -0.0423(3) 0.8358(5) 0.0489(13) Uani 1 1 d . . . H9A H 0.5787 -0.0785 0.8879 0.059 Uiso 1 1 calc R . . H9B H 0.5774 0.0095 0.8157 0.059 Uiso 1 1 calc R . . C10 C 0.8316(6) -0.0206(3) 0.9188(5) 0.0373(11) Uani 1 1 d . . . C11 C 0.8483(6) 0.0498(3) 1.0011(5) 0.0459(13) Uani 1 1 d . . . H11 H 0.7454 0.0844 1.0025 0.055 Uiso 1 1 calc R . . C12 C 0.9874(7) -0.0704(3) 0.9190(5) 0.0476(13) Uani 1 1 d . . . H12 H 0.9813 -0.1183 0.8648 0.057 Uiso 1 1 calc R . . C13 C 0.7445(6) 0.0439(3) 0.6035(5) 0.0421(12) Uani 1 1 d . . . H13 H 0.7421 0.0739 0.6822 0.050 Uiso 1 1 calc R . . C14 C 0.7075(6) -0.0426(3) 0.6025(5) 0.0404(12) Uani 1 1 d . . . C15 C 0.7140(6) -0.0856(3) 0.4837(6) 0.0486(13) Uani 1 1 d . . . H15 H 0.6881 -0.1434 0.4776 0.058 Uiso 1 1 calc R . . C16 C 0.7584(7) -0.0428(4) 0.3761(6) 0.0545(15) Uani 1 1 d . . . H16 H 0.7669 -0.0715 0.2971 0.065 Uiso 1 1 calc R . . C17 C 0.7906(7) 0.0435(4) 0.3858(5) 0.0511(14) Uani 1 1 d . . . H17 H 0.8183 0.0726 0.3115 0.061 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 Pb1 0.03535(15) 0.04627(17) 0.02316(15) 0.000 0.00530(10) 0.000 N1 0.056(3) 0.039(3) 0.060(3) 0.002(2) 0.001(2) -0.007(2) N2 0.041(2) 0.045(3) 0.038(3) 0.000(2) 0.0069(19) 0.0023(18) O1 0.044(2) 0.052(3) 0.022(2) 0.000 0.006(2) 0.000 O2 0.036(3) 0.112(5) 0.027(3) 0.000 0.005(2) 0.000 O3 0.042(2) 0.054(3) 0.020(2) 0.000 0.008(2) 0.000 O4 0.041(3) 0.092(4) 0.024(3) 0.000 0.003(2) 0.000 C1 0.041(4) 0.034(4) 0.020(4) 0.000 0.008(3) 0.000 C2 0.039(4) 0.034(4) 0.025(4) 0.000 0.007(3) 0.000 C3 0.041(3) 0.030(3) 0.019(3) 0.000 0.004(3) 0.000 C4 0.038(3) 0.023(3) 0.027(4) 0.000 0.007(3) 0.000 C5 0.039(3) 0.030(3) 0.023(3) 0.000 0.004(3) 0.000 C6 0.042(4) 0.044(4) 0.028(4) 0.000 0.013(3) 0.000 C7 0.036(4) 0.065(5) 0.035(4) 0.000 0.007(3) 0.000 C8 0.046(4) 0.041(4) 0.026(4) 0.000 -0.001(3) 0.000 C9 0.048(3) 0.050(3) 0.051(3) 0.011(3) 0.014(2) 0.002(2) C10 0.041(3) 0.031(3) 0.041(3) 0.008(2) 0.009(2) 0.004(2) C11 0.043(3) 0.039(3) 0.057(3) 0.003(3) 0.010(2) 0.009(2) C12 0.050(3) 0.040(3) 0.054(3) -0.004(3) 0.016(3) 0.001(2) C13 0.038(3) 0.047(3) 0.041(3) -0.003(2) 0.004(2) 0.004(2) C14 0.032(2) 0.041(3) 0.046(3) 0.001(2) -0.001(2) -0.001(2) C15 0.038(3) 0.043(3) 0.062(4) -0.010(3) -0.003(2) 0.002(2) C16 0.051(3) 0.057(4) 0.051(4) -0.017(3) -0.004(3) 0.008(3) C17 0.049(3) 0.061(4) 0.043(3) 0.000(3) 0.008(2) 0.009(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 Pb1 O1 2.369(4) . ? Pb1 O3 2.433(4) 1_554 ? Pb1 O2 2.607(5) . ? Pb1 N2 2.620(4) 4_565 ? Pb1 N2 2.620(4) . ? Pb1 O4 2.718(4) 1_554 ? N1 C14 1.377(6) . ? N1 C9 1.433(6) . ? N1 H1 0.8600 . ? N2 C17 1.322(6) . ? N2 C13 1.332(6) . ? O1 C1 1.251(7) . ? O2 C1 1.244(7) . ? O3 C2 1.267(7) . ? O3 Pb1 2.433(4) 1_556 ? O4 C2 1.240(7) . ? O4 Pb1 2.718(4) 1_556 ? C1 C3 1.505(8) . ? C2 C5 1.487(8) . ? C3 C4 1.378(8) . ? C3 C8 1.390(8) . ? C4 C5 1.380(8) . ? C4 H4 0.9300 . ? C5 C6 1.390(8) . ? C6 C7 1.373(9) . ? C6 H6 0.9300 . ? C7 C8 1.387(9) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.507(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C12 1.382(6) . ? C10 C11 1.382(7) . ? C11 C12 1.377(6) 3_757 ? C11 H11 0.9300 . ? C12 C11 1.377(6) 3_757 ? C12 H12 0.9300 . ? C13 C14 1.390(6) . ? C13 H13 0.9300 . ? C14 C15 1.389(7) . ? C15 C16 1.363(7) . ? C15 H15 0.9300 . ? C16 C17 1.381(7) . ? C16 H16 0.9300 . ? C17 H17 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 O1 Pb1 O3 76.57(14) . 1_554 ? O1 Pb1 O2 52.07(14) . . ? O3 Pb1 O2 128.64(14) 1_554 . ? O1 Pb1 N2 81.39(8) . 4_565 ? O3 Pb1 N2 84.31(8) 1_554 4_565 ? O2 Pb1 N2 87.72(9) . 4_565 ? O1 Pb1 N2 81.39(9) . . ? O3 Pb1 N2 84.31(8) 1_554 . ? O2 Pb1 N2 87.72(9) . . ? N2 Pb1 N2 161.16(16) 4_565 . ? O1 Pb1 O4 126.65(14) . 1_554 ? O3 Pb1 O4 50.07(13) 1_554 1_554 ? O2 Pb1 O4 178.71(13) . 1_554 ? N2 Pb1 O4 92.07(9) 4_565 1_554 ? N2 Pb1 O4 92.07(9) . 1_554 ? C14 N1 C9 123.0(4) . . ? C14 N1 H1 118.5 . . ? C9 N1 H1 118.5 . . ? C17 N2 C13 118.7(5) . . ? C17 N2 Pb1 117.5(3) . . ? C13 N2 Pb1 123.8(3) . . ? C1 O1 Pb1 97.9(4) . . ? C1 O2 Pb1 86.9(4) . . ? C2 O3 Pb1 100.3(4) . 1_556 ? C2 O4 Pb1 87.4(4) . 1_556 ? O2 C1 O1 123.1(6) . . ? O2 C1 C3 117.9(5) . . ? O1 C1 C3 119.0(5) . . ? O4 C2 O3 122.3(6) . . ? O4 C2 C5 118.9(6) . . ? O3 C2 C5 118.8(5) . . ? C4 C3 C8 118.4(6) . . ? C4 C3 C1 119.9(5) . . ? C8 C3 C1 121.7(5) . . ? C3 C4 C5 122.7(5) . . ? C3 C4 H4 118.7 . . ? C5 C4 H4 118.7 . . ? C4 C5 C6 117.9(6) . . ? C4 C5 C2 119.0(5) . . ? C6 C5 C2 123.1(6) . . ? C7 C6 C5 120.7(6) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 120.4(6) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C7 C8 C3 119.9(6) . . ? C7 C8 H8 120.0 . . ? C3 C8 H8 120.0 . . ? N1 C9 C10 113.7(4) . . ? N1 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? N1 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C12 C10 C11 117.4(4) . . ? C12 C10 C9 122.1(4) . . ? C11 C10 C9 120.5(4) . . ? C12 C11 C10 122.1(5) 3_757 . ? C12 C11 H11 118.9 3_757 . ? C10 C11 H11 118.9 . . ? C11 C12 C10 120.5(5) 3_757 . ? C11 C12 H12 119.7 3_757 . ? C10 C12 H12 119.7 . . ? N2 C13 C14 123.2(5) . . ? N2 C13 H13 118.4 . . ? C14 C13 H13 118.4 . . ? N1 C14 C15 120.9(5) . . ? N1 C14 C13 122.2(5) . . ? C15 C14 C13 116.9(5) . . ? C16 C15 C14 119.8(5) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 119.3(5) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? N2 C17 C16 122.1(5) . . ? N2 C17 H17 119.0 . . ? C16 C17 H17 119.0 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.105 _refine_diff_density_min -1.100 _refine_diff_density_rms 0.107 _database_code_depnum_ccdc_archive 'CCDC 933893' ####################################################################### # # 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_120314c #TrackingRef '111205a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H11 N2 O4 S Zn' _chemical_formula_weight 380.69 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' Zn Zn 0.2839 1.4301 '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 18.0502(7) _cell_length_b 12.1923(3) _cell_length_c 15.6893(7) _cell_angle_alpha 90.00 _cell_angle_beta 117.445(2) _cell_angle_gamma 90.00 _cell_volume 3064.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2472 _cell_measurement_theta_min 2.8525 _cell_measurement_theta_max 28.1726 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.650 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1544 _exptl_absorpt_coefficient_mu 1.760 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.85250 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5287 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_unetI/netI 0.0253 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2706 _reflns_number_gt 2455 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'publCIF (Westrip, 2010)' _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^)+(0.0331P)^2^+2.0895P] 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 2706 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0282 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_ref 0.0627 _refine_ls_wR_factor_gt 0.0606 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 Zn1 Zn 0.330681(13) 0.313208(18) 0.539529(16) 0.01759(9) Uani 1 1 d . . . S1 S 0.27443(3) 0.01323(5) 0.76772(4) 0.02813(14) Uani 1 1 d . . . N1 N 0.42461(10) 0.42273(13) 0.58122(12) 0.0208(4) Uani 1 1 d . . . N2 N 0.46683(13) 0.70388(15) 0.53314(17) 0.0401(5) Uani 1 1 d . . . H2 H 0.5078 0.7495 0.5560 0.048 Uiso 1 1 calc R . . O1 O 0.37275(9) 0.20970(13) 0.65446(11) 0.0315(4) Uani 1 1 d . . . O2 O 0.24664(9) 0.13033(12) 0.59443(10) 0.0315(4) Uani 1 1 d . . . O3 O 0.37312(10) -0.19837(12) 0.97507(11) 0.0311(4) Uani 1 1 d . . . O4 O 0.24741(9) -0.11712(12) 0.90873(11) 0.0308(4) Uani 1 1 d . . . C1 C 0.32120(13) 0.14301(17) 0.65780(15) 0.0240(4) Uani 1 1 d . . . C2 C 0.34911(12) 0.07232(17) 0.74422(15) 0.0229(4) Uani 1 1 d . . . C3 C 0.42722(14) 0.04171(19) 0.80961(16) 0.0298(5) Uani 1 1 d . . . H3 H 0.4757 0.0673 0.8094 0.036 Uiso 1 1 calc R . . C4 C 0.42659(13) -0.03318(18) 0.87770(16) 0.0287(5) Uani 1 1 d . . . H4 H 0.4746 -0.0640 0.9262 0.034 Uiso 1 1 calc R . . C5 C 0.34808(13) -0.05562(17) 0.86489(15) 0.0230(4) Uani 1 1 d . . . C6 C 0.32055(13) -0.12916(17) 0.92111(15) 0.0238(5) Uani 1 1 d . . . C7 C 0.41348(13) 0.52378(16) 0.54334(16) 0.0245(5) Uani 1 1 d . . . H7 H 0.3609 0.5431 0.4953 0.029 Uiso 1 1 calc R . . C8 C 0.47767(13) 0.60108(17) 0.57319(17) 0.0276(5) Uani 1 1 d . . . C9 C 0.55469(14) 0.5701(2) 0.64803(19) 0.0371(6) Uani 1 1 d . . . H9 H 0.5988 0.6197 0.6719 0.044 Uiso 1 1 calc R . . C10 C 0.56539(14) 0.4671(2) 0.68637(18) 0.0354(6) Uani 1 1 d . . . H10 H 0.6167 0.4465 0.7363 0.043 Uiso 1 1 calc R . . C11 C 0.49997(13) 0.39401(19) 0.65068(16) 0.0279(5) Uani 1 1 d . . . H11 H 0.5082 0.3231 0.6753 0.034 Uiso 1 1 calc R . . C12 C 0.38889(16) 0.7375(2) 0.4539(2) 0.0437(7) Uani 1 1 d . . . H12A H 0.3742 0.6857 0.4016 0.052 Uiso 1 1 calc R . . H12B H 0.3966 0.8086 0.4314 0.052 Uiso 1 1 calc R . . C13 C 0.31714(15) 0.74499(18) 0.47837(19) 0.0355(6) Uani 1 1 d . . . C14 C 0.32963(17) 0.7727(2) 0.5698(2) 0.0485(7) Uani 1 1 d . . . H14 H 0.3832 0.7880 0.6176 0.058 Uiso 1 1 calc R . . C15 C 0.23703(17) 0.7222(2) 0.4096(2) 0.0482(7) Uani 1 1 d . . . H15 H 0.2275 0.7031 0.3480 0.058 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 Zn1 0.01895(14) 0.01814(14) 0.01715(14) -0.00080(9) 0.00958(10) -0.00374(8) S1 0.0192(3) 0.0340(3) 0.0296(3) 0.0135(3) 0.0099(2) -0.0006(2) N1 0.0194(8) 0.0228(9) 0.0228(9) -0.0020(8) 0.0118(7) -0.0038(7) N2 0.0337(11) 0.0240(10) 0.0700(16) 0.0028(10) 0.0302(11) -0.0058(8) O1 0.0295(8) 0.0352(9) 0.0318(9) 0.0139(7) 0.0159(7) -0.0015(7) O2 0.0320(9) 0.0334(9) 0.0209(8) 0.0077(7) 0.0052(7) -0.0036(7) O3 0.0309(9) 0.0312(8) 0.0325(9) 0.0155(7) 0.0156(7) 0.0028(7) O4 0.0314(8) 0.0311(8) 0.0394(9) 0.0102(8) 0.0245(7) 0.0025(7) C1 0.0304(12) 0.0245(11) 0.0198(11) 0.0033(9) 0.0139(9) 0.0013(9) C2 0.0241(11) 0.0252(11) 0.0219(11) 0.0030(9) 0.0128(9) -0.0037(9) C3 0.0233(11) 0.0372(13) 0.0328(13) 0.0098(11) 0.0164(10) 0.0001(9) C4 0.0224(11) 0.0346(12) 0.0269(12) 0.0112(10) 0.0095(10) 0.0040(9) C5 0.0253(11) 0.0232(11) 0.0213(11) 0.0061(9) 0.0115(9) 0.0029(8) C6 0.0290(12) 0.0231(11) 0.0225(11) 0.0018(9) 0.0145(9) -0.0018(9) C7 0.0212(10) 0.0231(11) 0.0312(12) -0.0008(10) 0.0138(9) -0.0001(8) C8 0.0269(11) 0.0222(11) 0.0426(14) -0.0046(10) 0.0236(10) -0.0045(9) C9 0.0242(12) 0.0384(14) 0.0486(16) -0.0100(12) 0.0167(11) -0.0145(10) C10 0.0192(11) 0.0488(15) 0.0339(13) 0.0015(12) 0.0085(10) -0.0046(10) C11 0.0231(11) 0.0327(12) 0.0287(12) 0.0050(10) 0.0126(9) 0.0004(9) C12 0.0505(16) 0.0320(13) 0.0660(19) 0.0116(13) 0.0418(15) 0.0061(12) C13 0.0410(14) 0.0229(12) 0.0510(16) 0.0079(11) 0.0285(12) 0.0086(10) C14 0.0374(14) 0.0542(16) 0.0558(18) -0.0056(15) 0.0230(13) 0.0056(13) C15 0.0509(17) 0.0549(16) 0.0453(16) -0.0025(14) 0.0278(14) 0.0090(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 Zn1 N1 2.0158(16) . ? Zn1 O2 2.0335(14) 7_556 ? Zn1 O1 2.0393(15) . ? Zn1 O3 2.0698(14) 6 ? Zn1 O4 2.1029(14) 4_556 ? Zn1 Zn1 3.0112(4) 7_556 ? S1 C5 1.711(2) . ? S1 C2 1.7116(19) . ? N1 C11 1.339(3) . ? N1 C7 1.342(3) . ? N2 C8 1.375(3) . ? N2 C12 1.442(3) . ? N2 H2 0.8600 . ? O1 C1 1.255(3) . ? O2 C1 1.261(3) . ? O2 Zn1 2.0335(14) 7_556 ? O3 C6 1.260(3) . ? O3 Zn1 2.0698(14) 6_556 ? O4 C6 1.251(2) . ? O4 Zn1 2.1029(14) 4_546 ? C1 C2 1.485(3) . ? C2 C3 1.359(3) . ? C3 C4 1.409(3) . ? C3 H3 0.9300 . ? C4 C5 1.364(3) . ? C4 H4 0.9300 . ? C5 C6 1.494(3) . ? C7 C8 1.396(3) . ? C7 H7 0.9300 . ? C8 C9 1.396(3) . ? C9 C10 1.368(4) . ? C9 H9 0.9300 . ? C10 C11 1.375(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.514(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C15 1.376(4) . ? C13 C14 1.388(4) . ? C14 C15 1.383(4) 7_566 ? C14 H14 0.9300 . ? C15 C14 1.383(4) 7_566 ? C15 H15 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 N1 Zn1 O2 100.67(6) . 7_556 ? N1 Zn1 O1 102.02(7) . . ? O2 Zn1 O1 157.20(6) 7_556 . ? N1 Zn1 O3 99.28(6) . 6 ? O2 Zn1 O3 87.49(6) 7_556 6 ? O1 Zn1 O3 86.71(6) . 6 ? N1 Zn1 O4 102.73(6) . 4_556 ? O2 Zn1 O4 89.96(6) 7_556 4_556 ? O1 Zn1 O4 87.21(6) . 4_556 ? O3 Zn1 O4 157.93(6) 6 4_556 ? N1 Zn1 Zn1 169.10(5) . 7_556 ? O2 Zn1 Zn1 71.02(4) 7_556 7_556 ? O1 Zn1 Zn1 86.72(4) . 7_556 ? O3 Zn1 Zn1 87.60(4) 6 7_556 ? O4 Zn1 Zn1 70.89(4) 4_556 7_556 ? C5 S1 C2 91.88(10) . . ? C11 N1 C7 119.27(18) . . ? C11 N1 Zn1 118.53(14) . . ? C7 N1 Zn1 122.18(14) . . ? C8 N2 C12 122.0(2) . . ? C8 N2 H2 119.0 . . ? C12 N2 H2 119.0 . . ? C1 O1 Zn1 117.18(14) . . ? C1 O2 Zn1 138.43(14) . 7_556 ? C6 O3 Zn1 116.58(13) . 6_556 ? C6 O4 Zn1 137.70(14) . 4_546 ? O1 C1 O2 126.08(19) . . ? O1 C1 C2 117.91(19) . . ? O2 C1 C2 116.00(18) . . ? C3 C2 C1 130.24(18) . . ? C3 C2 S1 111.59(16) . . ? C1 C2 S1 118.13(15) . . ? C2 C3 C4 112.46(19) . . ? C2 C3 H3 123.8 . . ? C4 C3 H3 123.8 . . ? C5 C4 C3 112.90(19) . . ? C5 C4 H4 123.6 . . ? C3 C4 H4 123.6 . . ? C4 C5 C6 129.71(19) . . ? C4 C5 S1 111.14(15) . . ? C6 C5 S1 119.15(15) . . ? O4 C6 O3 126.63(19) . . ? O4 C6 C5 116.88(18) . . ? O3 C6 C5 116.48(18) . . ? N1 C7 C8 122.6(2) . . ? N1 C7 H7 118.7 . . ? C8 C7 H7 118.7 . . ? N2 C8 C9 120.5(2) . . ? N2 C8 C7 122.7(2) . . ? C9 C8 C7 116.8(2) . . ? C10 C9 C8 120.2(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 119.7(2) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? N1 C11 C10 121.4(2) . . ? N1 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? N2 C12 C13 114.0(2) . . ? N2 C12 H12A 108.7 . . ? C13 C12 H12A 108.7 . . ? N2 C12 H12B 108.7 . . ? C13 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C15 C13 C14 118.1(2) . . ? C15 C13 C12 120.1(2) . . ? C14 C13 C12 121.8(2) . . ? C15 C14 C13 120.5(3) 7_566 . ? C15 C14 H14 119.7 7_566 . ? C13 C14 H14 119.7 . . ? C13 C15 C14 121.4(3) . 7_566 ? C13 C15 H15 119.3 . . ? C14 C15 H15 119.3 7_566 . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.284 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.072 #===END _database_code_depnum_ccdc_archive 'CCDC 933894'