# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_t #TrackingRef 't.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 Cd N4 O4 ' _chemical_formula_sum 'C14 H14 Cd N4 O4' _chemical_formula_weight 414.70 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'I b a 2' _symmetry_space_group_name_Hall 'I 2 -2c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x, y, z+1/2' 'x, -y, z+1/2' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1' 'x+1/2, -y+1/2, z+1' _cell_length_a 12.121(2) _cell_length_b 17.543(4) _cell_length_c 6.9785(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1483.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.856 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 1.498 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7058 _exptl_absorpt_correction_T_max 0.7742 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3194 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1291 _reflns_number_gt 1130 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0158P)^2^+1.3976P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(7) _refine_ls_number_reflns 1291 _refine_ls_number_parameters 105 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0233 _refine_ls_R_factor_gt 0.0190 _refine_ls_wR_factor_ref 0.0488 _refine_ls_wR_factor_gt 0.0455 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd -0.5000 0.5000 -0.0899(2) 0.03334(10) Uani 1 2 d S . . O1 O -0.37945(16) 0.52849(11) -0.3378(5) 0.0355(4) Uani 1 1 d . . . O3 O -0.4759(2) 0.37448(13) -0.0824(10) 0.0555(7) Uani 1 1 d . . . N1 N -0.35142(19) 0.60492(14) -0.3494(6) 0.0357(6) Uani 1 1 d . . . H1 H -0.2980 0.6226 -0.2791 0.043 Uiso 1 1 d R . . N3 N -0.3321(3) 0.96917(19) -0.4647(6) 0.0681(11) Uani 1 1 d . . . H3A H -0.2748 0.9887 -0.4078 0.082 Uiso 1 1 d R . . H3B H -0.3806 0.9989 -0.5180 0.082 Uiso 1 1 d R . . C1 C -0.4049(3) 0.65092(19) -0.4662(5) 0.0351(8) Uani 1 1 d . . . C2 C -0.3794(3) 0.73298(18) -0.4642(5) 0.0334(7) Uani 1 1 d . . . C3 C -0.4546(3) 0.7819(2) -0.5521(6) 0.0439(10) Uani 1 1 d . . . H3 H -0.5180 0.7613 -0.6100 0.053 Uiso 1 1 calc R . . C4 C -0.4384(3) 0.8590(2) -0.5562(6) 0.0504(11) Uani 1 1 d . . . H4 H -0.4903 0.8905 -0.6175 0.061 Uiso 1 1 calc R . . C5 C -0.3459(3) 0.8912(2) -0.4705(6) 0.0426(9) Uani 1 1 d . . . C6 C -0.2692(3) 0.8428(2) -0.3861(5) 0.0418(9) Uani 1 1 d . . . H6 H -0.2051 0.8633 -0.3304 0.050 Uiso 1 1 calc R . . C7 C -0.2856(3) 0.7650(2) -0.3829(5) 0.0394(9) Uani 1 1 d . . . H7 H -0.2327 0.7333 -0.3251 0.047 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 0.05144(18) 0.02312(15) 0.02546(15) 0.000 0.000 0.00324(16) O1 0.0488(11) 0.0235(9) 0.0342(10) 0.0037(19) 0.0021(16) 0.0014(9) O3 0.076(2) 0.0279(11) 0.0630(17) -0.002(2) -0.027(3) 0.0079(12) N1 0.0408(13) 0.0302(13) 0.0360(15) -0.0020(18) -0.0046(18) -0.0026(11) N3 0.066(2) 0.0279(17) 0.110(3) -0.002(2) -0.026(2) -0.0078(17) C1 0.043(2) 0.0327(18) 0.0293(19) -0.0022(15) -0.0005(16) 0.0005(16) C2 0.0426(18) 0.0287(17) 0.0291(17) -0.0010(15) -0.0014(15) -0.0021(15) C3 0.0446(18) 0.0328(18) 0.054(3) -0.0035(18) -0.0134(18) -0.0053(16) C4 0.050(2) 0.0322(18) 0.069(3) 0.000(2) -0.022(2) 0.0010(16) C5 0.048(2) 0.0301(18) 0.050(2) -0.0007(18) -0.0035(18) -0.0090(17) C6 0.0420(18) 0.0364(18) 0.047(3) -0.0033(16) -0.0071(16) -0.0102(15) C7 0.0406(17) 0.040(2) 0.038(2) 0.0039(16) -0.0073(15) 0.0006(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 O3 2.222(2) . ? Cd1 O3 2.222(2) 2_465 ? Cd1 O1 2.319(3) . ? Cd1 O1 2.319(3) 2_465 ? Cd1 O1 2.341(3) 4_565 ? Cd1 O1 2.341(3) 3_455 ? Cd1 Cd1 3.4892(7) 3_455 ? Cd1 Cd1 3.4893(7) 3_454 ? O1 N1 1.385(3) . ? O1 Cd1 2.341(3) 3_454 ? O3 C1 1.264(6) 4_565 ? N1 C1 1.317(4) . ? N1 H1 0.8702 . ? N3 C5 1.378(5) . ? N3 H3A 0.8701 . ? N3 H3B 0.8699 . ? C1 O3 1.264(6) 4_564 ? C1 C2 1.472(4) . ? C2 C3 1.394(5) . ? C2 C7 1.390(5) . ? C3 C4 1.368(5) . ? C3 H3 0.9400 . ? C4 C5 1.391(5) . ? C4 H4 0.9400 . ? C5 C6 1.391(5) . ? C6 C7 1.378(5) . ? C6 H6 0.9400 . ? C7 H7 0.9400 . ? 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 177.3(4) . 2_465 ? O3 Cd1 O1 98.54(19) . . ? O3 Cd1 O1 83.50(13) 2_465 . ? O3 Cd1 O1 83.49(13) . 2_465 ? O3 Cd1 O1 98.54(19) 2_465 2_465 ? O1 Cd1 O1 83.50(15) . 2_465 ? O3 Cd1 O1 71.86(14) . 4_565 ? O3 Cd1 O1 106.01(19) 2_465 4_565 ? O1 Cd1 O1 102.32(8) . 4_565 ? O1 Cd1 O1 155.22(9) 2_465 4_565 ? O3 Cd1 O1 106.02(19) . 3_455 ? O3 Cd1 O1 71.86(14) 2_465 3_455 ? O1 Cd1 O1 155.22(9) . 3_455 ? O1 Cd1 O1 102.32(8) 2_465 3_455 ? O1 Cd1 O1 82.56(15) 4_565 3_455 ? O3 Cd1 Cd1 88.65(19) . 3_455 ? O3 Cd1 Cd1 88.65(19) 2_465 3_455 ? O1 Cd1 Cd1 138.25(8) . 3_455 ? O1 Cd1 Cd1 138.25(8) 2_465 3_455 ? O1 Cd1 Cd1 41.28(7) 4_565 3_455 ? O1 Cd1 Cd1 41.28(7) 3_455 3_455 ? O3 Cd1 Cd1 91.35(19) . 3_454 ? O3 Cd1 Cd1 91.35(19) 2_465 3_454 ? O1 Cd1 Cd1 41.75(8) . 3_454 ? O1 Cd1 Cd1 41.75(8) 2_465 3_454 ? O1 Cd1 Cd1 138.72(7) 4_565 3_454 ? O1 Cd1 Cd1 138.72(7) 3_455 3_454 ? Cd1 Cd1 Cd1 180.0 3_455 3_454 ? N1 O1 Cd1 114.0(2) . . ? N1 O1 Cd1 108.4(2) . 3_454 ? Cd1 O1 Cd1 96.97(7) . 3_454 ? C1 O3 Cd1 117.0(3) 4_565 . ? C1 N1 O1 120.6(3) . . ? C1 N1 H1 119.8 . . ? O1 N1 H1 119.7 . . ? C5 N3 H3A 120.1 . . ? C5 N3 H3B 120.0 . . ? H3A N3 H3B 119.9 . . ? O3 C1 N1 121.1(3) 4_564 . ? O3 C1 C2 119.6(3) 4_564 . ? N1 C1 C2 119.3(3) . . ? C3 C2 C7 117.7(3) . . ? C3 C2 C1 117.4(3) . . ? C7 C2 C1 124.8(3) . . ? C4 C3 C2 121.7(3) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 120.5(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? N3 C5 C6 120.8(3) . . ? N3 C5 C4 120.9(3) . . ? C6 C5 C4 118.2(3) . . ? C7 C6 C5 121.0(3) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C2 120.8(3) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Cd1 O1 N1 -163.9(2) . . . . ? O3 Cd1 O1 N1 14.3(3) 2_465 . . . ? O1 Cd1 O1 N1 113.7(2) 2_465 . . . ? O1 Cd1 O1 N1 -90.69(18) 4_565 . . . ? O1 Cd1 O1 N1 8.3(4) 3_455 . . . ? Cd1 Cd1 O1 N1 -66.3(2) 3_455 . . . ? Cd1 Cd1 O1 N1 113.7(2) 3_454 . . . ? O3 Cd1 O1 Cd1 82.39(12) . . . 3_454 ? O3 Cd1 O1 Cd1 -99.40(18) 2_465 . . 3_454 ? O1 Cd1 O1 Cd1 0.0 2_465 . . 3_454 ? O1 Cd1 O1 Cd1 155.57(9) 4_565 . . 3_454 ? O1 Cd1 O1 Cd1 -105.4(3) 3_455 . . 3_454 ? Cd1 Cd1 O1 Cd1 180.0 3_455 . . 3_454 ? O3 Cd1 O3 C1 -44.9(5) 2_465 . . 4_565 ? O1 Cd1 O3 C1 93.8(5) . . . 4_565 ? O1 Cd1 O3 C1 176.2(5) 2_465 . . 4_565 ? O1 Cd1 O3 C1 -6.5(4) 4_565 . . 4_565 ? O1 Cd1 O3 C1 -82.8(4) 3_455 . . 4_565 ? Cd1 Cd1 O3 C1 -44.9(5) 3_455 . . 4_565 ? Cd1 Cd1 O3 C1 135.1(5) 3_454 . . 4_565 ? Cd1 O1 N1 C1 -95.6(4) . . . . ? Cd1 O1 N1 C1 11.1(4) 3_454 . . . ? O1 N1 C1 O3 -6.4(6) . . . 4_564 ? O1 N1 C1 C2 175.1(3) . . . . ? O3 C1 C2 C3 17.0(6) 4_564 . . . ? N1 C1 C2 C3 -164.4(3) . . . . ? O3 C1 C2 C7 -162.3(4) 4_564 . . . ? N1 C1 C2 C7 16.2(5) . . . . ? C7 C2 C3 C4 -1.1(6) . . . . ? C1 C2 C3 C4 179.5(4) . . . . ? C2 C3 C4 C5 -0.5(7) . . . . ? C3 C4 C5 N3 -176.4(4) . . . . ? C3 C4 C5 C6 1.9(6) . . . . ? N3 C5 C6 C7 176.6(4) . . . . ? C4 C5 C6 C7 -1.7(6) . . . . ? C5 C6 C7 C2 0.0(5) . . . . ? C3 C2 C7 C6 1.4(5) . . . . ? C1 C2 C7 C6 -179.3(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.217 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 882293' ####################################################################### # # 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_c7010 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H36 N8 O12 Zn2' _chemical_formula_sum 'C28 H36 N8 O12 Zn2' _chemical_formula_weight 807.39 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' 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 'P 21/n' _symmetry_space_group_name_HALL '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.5931(6) _cell_length_b 7.6567(4) _cell_length_c 19.8339(11) _cell_angle_alpha 90.00 _cell_angle_beta 93.2620(10) _cell_angle_gamma 90.00 _cell_volume 1606.09(15) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4699 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 27.89 _exptl_crystal_description Rod _exptl_crystal_colour pink _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.670 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 1.570 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6501 _exptl_absorpt_correction_T_max 0.7140 _exptl_absorpt_process_details 'SADABS (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEXII CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10613 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_unetI/netI 0.0239 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.95 _reflns_number_total 3828 _reflns_number_gt 3344 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX-II (Bruker, 2005)' _computing_cell_refinement 'SAINT (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0400P)^2^+0.9143P] 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 3828 _refine_ls_number_parameters 229 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0340 _refine_ls_R_factor_gt 0.0287 _refine_ls_wR_factor_ref 0.0795 _refine_ls_wR_factor_gt 0.0769 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.02060(2) 0.80489(3) 0.026507(10) 0.02161(8) Uani 1 1 d . . . O1 O 0.02584(13) 0.73641(18) -0.07498(6) 0.0255(3) Uani 1 1 d . . . C1 C 0.12695(18) 0.7953(2) -0.17768(9) 0.0215(4) Uani 1 1 d . . . N1 N 0.16495(14) 0.9572(2) -0.07518(7) 0.0217(3) Uani 1 1 d . . . H1 H 0.2257 1.0090 -0.0941 0.026 Uiso 1 1 calc R . . N2 N 0.15355(18) 0.7472(3) -0.38699(8) 0.0339(4) Uani 1 1 d . . . H2A H 0.2199 0.7838 -0.4057 0.041 Uiso 1 1 calc R . . H2B H 0.0934 0.6984 -0.4111 0.041 Uiso 1 1 calc R . . C2 C 0.23213(19) 0.8597(3) -0.20909(10) 0.0268(4) Uani 1 1 d . . . H2 H 0.2974 0.9125 -0.1832 0.032 Uiso 1 1 calc R . . O2 O 0.12983(12) 1.01117(17) -0.01212(6) 0.0221(3) Uani 1 1 d . . . O3 O 0.03659(14) 0.83793(19) 0.12943(7) 0.0298(3) Uani 1 1 d . . . N3 N 0.18083(16) 0.6273(2) 0.12363(8) 0.0298(4) Uani 1 1 d . . . H3A H 0.2297 0.5516 0.1437 0.036 Uiso 1 1 calc R . . C3 C 0.24014(19) 0.8456(3) -0.27810(10) 0.0284(4) Uani 1 1 d . . . H3 H 0.3108 0.8892 -0.2983 0.034 Uiso 1 1 calc R . . O4 O 0.17430(13) 0.63793(19) 0.05427(7) 0.0286(3) Uani 1 1 d . . . C4 C 0.14353(19) 0.7669(3) -0.31783(9) 0.0256(4) Uani 1 1 d . . . N4 N 0.1456(2) 0.7096(4) 0.44504(10) 0.0548(7) Uani 1 1 d . . . H4A H 0.2062 0.6535 0.4660 0.066 Uiso 1 1 calc R . . H4B H 0.0887 0.7600 0.4674 0.066 Uiso 1 1 calc R . . O5 O -0.11619(13) 0.60027(17) 0.04041(7) 0.0272(3) Uani 1 1 d . . . H5A H -0.1441 0.5439 0.0058 0.041 Uiso 1 1 d R . . H5B H -0.0828 0.5101 0.0590 0.041 Uiso 1 1 d R . . C5 C 0.03982(19) 0.6977(3) -0.28628(10) 0.0283(4) Uani 1 1 d . . . H5 H -0.0244 0.6421 -0.3120 0.034 Uiso 1 1 calc R . . C6 C 0.03225(18) 0.7114(2) -0.21736(10) 0.0251(4) Uani 1 1 d . . . H6 H -0.0369 0.6640 -0.1970 0.030 Uiso 1 1 calc R . . O6 O 0.4079(2) 0.7825(5) 0.02895(14) 0.0903(9) Uani 1 1 d D . . H6A H 0.3360 0.7348 0.0323 0.135 Uiso 1 1 d RD . . H6B H 0.401(2) 0.850(5) -0.0050(17) 0.135 Uiso 1 1 d D . . C7 C 0.10517(17) 0.8269(2) -0.10588(9) 0.0207(3) Uani 1 1 d . . . C8 C 0.12490(18) 0.7264(2) 0.23384(9) 0.0232(4) Uani 1 1 d . . . C9 C 0.03568(19) 0.8122(3) 0.27039(10) 0.0288(4) Uani 1 1 d . . . H9 H -0.0297 0.8728 0.2475 0.035 Uiso 1 1 calc R . . C10 C 0.0424(2) 0.8091(3) 0.34009(11) 0.0338(5) Uani 1 1 d . . . H10 H -0.0184 0.8676 0.3635 0.041 Uiso 1 1 calc R . . C11 C 0.1396(2) 0.7189(3) 0.37585(10) 0.0310(4) Uani 1 1 d . . . C12 C 0.2316(2) 0.6375(3) 0.33924(10) 0.0327(5) Uani 1 1 d . . . H12 H 0.2990 0.5810 0.3621 0.039 Uiso 1 1 calc R . . C13 C 0.22400(19) 0.6398(3) 0.26966(10) 0.0293(4) Uani 1 1 d . . . H13 H 0.2855 0.5832 0.2462 0.035 Uiso 1 1 calc R . . C14 C 0.11227(18) 0.7329(2) 0.15942(9) 0.0231(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 Zn1 0.02976(13) 0.01951(12) 0.01580(12) 0.00055(8) 0.00334(8) 0.00030(8) O1 0.0346(7) 0.0243(7) 0.0181(6) -0.0004(5) 0.0066(5) -0.0067(6) C1 0.0260(9) 0.0208(9) 0.0181(8) -0.0007(6) 0.0046(7) 0.0017(7) N1 0.0249(7) 0.0246(8) 0.0161(7) -0.0008(6) 0.0057(6) -0.0013(6) N2 0.0371(9) 0.0460(10) 0.0193(8) -0.0034(7) 0.0090(7) -0.0016(8) C2 0.0270(9) 0.0292(10) 0.0245(9) -0.0044(8) 0.0049(7) -0.0046(8) O2 0.0303(7) 0.0223(6) 0.0139(6) -0.0020(5) 0.0032(5) -0.0008(5) O3 0.0390(8) 0.0310(7) 0.0189(6) 0.0001(5) -0.0015(6) 0.0115(6) N3 0.0354(9) 0.0348(9) 0.0190(8) 0.0029(7) 0.0015(7) 0.0108(7) C3 0.0295(10) 0.0305(10) 0.0263(10) -0.0002(8) 0.0114(8) -0.0037(8) O4 0.0354(7) 0.0327(7) 0.0180(6) -0.0012(5) 0.0043(5) 0.0043(6) C4 0.0314(10) 0.0267(9) 0.0192(9) -0.0003(7) 0.0070(7) 0.0048(8) N4 0.0479(12) 0.095(2) 0.0207(9) 0.0043(10) -0.0010(9) 0.0207(12) O5 0.0353(7) 0.0209(7) 0.0257(7) -0.0016(5) 0.0050(6) -0.0026(6) C5 0.0277(9) 0.0340(11) 0.0233(9) -0.0049(8) 0.0028(8) -0.0024(8) C6 0.0259(9) 0.0277(10) 0.0225(9) -0.0023(7) 0.0070(7) -0.0020(7) O6 0.0391(11) 0.148(3) 0.0838(18) 0.0394(17) 0.0060(11) -0.0029(14) C7 0.0246(9) 0.0200(8) 0.0177(8) 0.0015(6) 0.0030(7) 0.0034(7) C8 0.0246(9) 0.0244(9) 0.0205(9) 0.0025(7) 0.0002(7) -0.0002(7) C9 0.0282(10) 0.0339(11) 0.0241(9) 0.0027(8) -0.0007(8) 0.0067(8) C10 0.0333(11) 0.0447(13) 0.0237(10) -0.0016(9) 0.0030(8) 0.0095(9) C11 0.0322(10) 0.0393(12) 0.0211(9) 0.0015(8) -0.0012(8) -0.0004(9) C12 0.0288(10) 0.0429(12) 0.0258(10) 0.0065(9) -0.0039(8) 0.0066(9) C13 0.0271(10) 0.0359(11) 0.0249(9) 0.0022(8) 0.0017(8) 0.0057(8) C14 0.0266(9) 0.0210(9) 0.0215(9) 0.0024(7) 0.0004(7) -0.0015(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 Zn1 O3 2.0545(14) . ? Zn1 O1 2.0838(13) . ? Zn1 O4 2.1180(14) . ? Zn1 O2 2.1264(13) . ? Zn1 O2 2.1337(13) 3_575 ? Zn1 O5 2.1623(13) . ? O1 C7 1.273(2) . ? C1 C6 1.396(3) . ? C1 C2 1.397(3) . ? C1 C7 1.475(2) . ? N1 C7 1.313(2) . ? N1 O2 1.3879(18) . ? N1 H1 0.8600 . ? N2 C4 1.390(2) . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? C2 C3 1.380(3) . ? C2 H2 0.9300 . ? O2 Zn1 2.1337(13) 3_575 ? O3 C14 1.261(2) . ? N3 C14 1.321(3) . ? N3 O4 1.376(2) . ? N3 H3A 0.8600 . ? C3 C4 1.393(3) . ? C3 H3 0.9300 . ? C4 C5 1.399(3) . ? N4 C11 1.372(3) . ? N4 H4A 0.8600 . ? N4 H4B 0.8600 . ? O5 H5A 0.8500 . ? O5 H5B 0.8499 . ? C5 C6 1.378(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? O6 H6A 0.8500 . ? O6 H6B 0.849(10) . ? C8 C9 1.389(3) . ? C8 C13 1.400(3) . ? C8 C14 1.475(3) . ? C9 C10 1.381(3) . ? C9 H9 0.9300 . ? C10 C11 1.399(3) . ? C10 H10 0.9300 . ? C11 C12 1.395(3) . ? C12 C13 1.378(3) . ? C12 H12 0.9300 . ? C13 H13 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 Zn1 O1 170.26(6) . . ? O3 Zn1 O4 78.31(5) . . ? O1 Zn1 O4 92.12(5) . . ? O3 Zn1 O2 104.53(5) . . ? O1 Zn1 O2 78.11(5) . . ? O4 Zn1 O2 96.66(5) . . ? O3 Zn1 O2 94.03(5) . 3_575 ? O1 Zn1 O2 95.60(5) . 3_575 ? O4 Zn1 O2 172.03(5) . 3_575 ? O2 Zn1 O2 83.06(5) . 3_575 ? O3 Zn1 O5 88.88(6) . . ? O1 Zn1 O5 89.76(5) . . ? O4 Zn1 O5 92.31(6) . . ? O2 Zn1 O5 165.12(5) . . ? O2 Zn1 O5 89.68(5) 3_575 . ? C7 O1 Zn1 112.50(11) . . ? C6 C1 C2 118.48(17) . . ? C6 C1 C7 118.21(16) . . ? C2 C1 C7 123.04(17) . . ? C7 N1 O2 119.81(15) . . ? C7 N1 H1 120.1 . . ? O2 N1 H1 120.1 . . ? C4 N2 H2A 120.0 . . ? C4 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C3 C2 C1 120.69(18) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? N1 O2 Zn1 106.44(10) . . ? N1 O2 Zn1 108.20(9) . 3_575 ? Zn1 O2 Zn1 96.94(5) . 3_575 ? C14 O3 Zn1 113.85(12) . . ? C14 N3 O4 120.21(16) . . ? C14 N3 H3A 119.9 . . ? O4 N3 H3A 119.9 . . ? C2 C3 C4 120.67(18) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? N3 O4 Zn1 106.85(10) . . ? N2 C4 C3 120.69(18) . . ? N2 C4 C5 120.42(19) . . ? C3 C4 C5 118.76(17) . . ? C11 N4 H4A 120.0 . . ? C11 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? Zn1 O5 H5A 118.0 . . ? Zn1 O5 H5B 112.3 . . ? H5A O5 H5B 93.1 . . ? C6 C5 C4 120.43(18) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 120.90(18) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? H6A O6 H6B 106.3 . . ? O1 C7 N1 120.31(16) . . ? O1 C7 C1 121.27(16) . . ? N1 C7 C1 118.33(16) . . ? C9 C8 C13 118.15(17) . . ? C9 C8 C14 118.72(17) . . ? C13 C8 C14 123.12(17) . . ? C10 C9 C8 121.13(18) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 120.7(2) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? N4 C11 C12 120.3(2) . . ? N4 C11 C10 121.5(2) . . ? C12 C11 C10 118.21(18) . . ? C13 C12 C11 120.85(19) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C8 120.92(19) . . ? C12 C13 H13 119.5 . . ? C8 C13 H13 119.5 . . ? O3 C14 N3 119.45(17) . . ? O3 C14 C8 120.83(17) . . ? N3 C14 C8 119.72(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Zn1 O1 C7 -95.5(3) . . . . ? O4 Zn1 O1 C7 -85.09(13) . . . . ? O2 Zn1 O1 C7 11.27(12) . . . . ? O2 Zn1 O1 C7 92.95(13) 3_575 . . . ? O5 Zn1 O1 C7 -177.39(13) . . . . ? C6 C1 C2 C3 2.1(3) . . . . ? C7 C1 C2 C3 -171.69(18) . . . . ? C7 N1 O2 Zn1 16.94(18) . . . . ? C7 N1 O2 Zn1 -86.34(16) . . . 3_575 ? O3 Zn1 O2 N1 156.27(10) . . . . ? O1 Zn1 O2 N1 -14.10(10) . . . . ? O4 Zn1 O2 N1 76.67(10) . . . . ? O2 Zn1 O2 N1 -111.35(11) 3_575 . . . ? O5 Zn1 O2 N1 -50.0(2) . . . . ? O3 Zn1 O2 Zn1 -92.38(5) . . . 3_575 ? O1 Zn1 O2 Zn1 97.25(6) . . . 3_575 ? O4 Zn1 O2 Zn1 -171.98(5) . . . 3_575 ? O2 Zn1 O2 Zn1 0.0 3_575 . . 3_575 ? O5 Zn1 O2 Zn1 61.3(2) . . . 3_575 ? O1 Zn1 O3 C14 1.6(4) . . . . ? O4 Zn1 O3 C14 -8.98(14) . . . . ? O2 Zn1 O3 C14 -102.92(14) . . . . ? O2 Zn1 O3 C14 173.21(14) 3_575 . . . ? O5 Zn1 O3 C14 83.61(14) . . . . ? C1 C2 C3 C4 0.0(3) . . . . ? C14 N3 O4 Zn1 -10.3(2) . . . . ? O3 Zn1 O4 N3 9.61(11) . . . . ? O1 Zn1 O4 N3 -168.61(12) . . . . ? O2 Zn1 O4 N3 113.12(12) . . . . ? O2 Zn1 O4 N3 25.6(4) 3_575 . . . ? O5 Zn1 O4 N3 -78.77(12) . . . . ? C2 C3 C4 N2 -177.72(19) . . . . ? C2 C3 C4 C5 -1.8(3) . . . . ? N2 C4 C5 C6 177.51(19) . . . . ? C3 C4 C5 C6 1.6(3) . . . . ? C4 C5 C6 C1 0.5(3) . . . . ? C2 C1 C6 C5 -2.4(3) . . . . ? C7 C1 C6 C5 171.76(17) . . . . ? Zn1 O1 C7 N1 -5.7(2) . . . . ? Zn1 O1 C7 C1 177.87(13) . . . . ? O2 N1 C7 O1 -8.5(3) . . . . ? O2 N1 C7 C1 168.08(15) . . . . ? C6 C1 C7 O1 22.2(3) . . . . ? C2 C1 C7 O1 -164.00(18) . . . . ? C6 C1 C7 N1 -154.37(17) . . . . ? C2 C1 C7 N1 19.5(3) . . . . ? C13 C8 C9 C10 -1.6(3) . . . . ? C14 C8 C9 C10 179.45(19) . . . . ? C8 C9 C10 C11 0.0(3) . . . . ? C9 C10 C11 N4 -177.9(2) . . . . ? C9 C10 C11 C12 2.1(3) . . . . ? N4 C11 C12 C13 177.4(2) . . . . ? C10 C11 C12 C13 -2.6(3) . . . . ? C11 C12 C13 C8 1.1(3) . . . . ? C9 C8 C13 C12 1.1(3) . . . . ? C14 C8 C13 C12 180.0(2) . . . . ? Zn1 O3 C14 N3 6.3(2) . . . . ? Zn1 O3 C14 C8 -173.56(13) . . . . ? O4 N3 C14 O3 3.2(3) . . . . ? O4 N3 C14 C8 -176.89(16) . . . . ? C9 C8 C14 O3 12.4(3) . . . . ? C13 C8 C14 O3 -166.6(2) . . . . ? C9 C8 C14 N3 -167.51(19) . . . . ? C13 C8 C14 N3 13.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N2 0.86 2.27 3.058(2) 152.2 2_554 N2 H2A O5 0.86 2.27 3.128(2) 174.8 4_675 N2 H2B O6 0.86 2.24 3.018(3) 149.9 4_575 N4 H4A O2 0.86 2.20 3.063(3) 175.3 2_545 N4 H4B O6 0.86 2.35 3.097(3) 145.2 4_576 O5 H5A O4 0.85 1.85 2.665(2) 160.6 3_565 O5 H5B O1 0.85 2.00 2.821(2) 161.6 3_565 O6 H6A O4 0.85 1.94 2.782(3) 171.2 . C12 H12 O3 0.93 2.55 3.392(3) 151.0 2_545 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.95 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.814 _refine_diff_density_min -0.443 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 948225' ####################################################################### # # 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_c7008 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H10 N2 O4 Zn' _chemical_formula_sum 'C9 H10 N2 O4 Zn' _chemical_formula_weight 275.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M 'I 41/a' _symmetry_space_group_name_Hall '-I 4ad' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 19.7107(9) _cell_length_b 19.7107(9) _cell_length_c 11.0593(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4296.7(5) _cell_formula_units_Z 16 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9893 _cell_measurement_theta_min 2.922 _cell_measurement_theta_max 26.334 _exptl_crystal_description rod _exptl_crystal_colour pink _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.704 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2240 _exptl_absorpt_coefficient_mu 2.286 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5283 _exptl_absorpt_correction_T_max 0.6214 _exptl_absorpt_process_details 'SADABS (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEXII CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26488 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_unetI/netI 0.0102 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 26.35 _reflns_number_total 2199 _reflns_number_gt 2020 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX-II (Bruker, 2005)' _computing_cell_refinement 'SAINT (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0574P)^2^+11.0616P] 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 2199 _refine_ls_number_parameters 146 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0369 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.1082 _refine_ls_wR_factor_gt 0.1058 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_restrained_S_all 1.134 _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 Zn1 Zn 0.213310(17) 0.422169(17) 0.03531(3) 0.03187(15) Uani 1 1 d U . . O1 O 0.28263(12) 0.35502(11) -0.04724(18) 0.0362(5) Uani 1 1 d . . . O3 O 0.19650(14) 0.36025(13) 0.1773(2) 0.0514(6) Uani 1 1 d . . . C8 C 0.21820(16) 0.35181(15) 0.2817(3) 0.0347(7) Uani 1 1 d . . . C7 C 0.28816(15) 0.36634(15) -0.1589(3) 0.0306(6) Uani 1 1 d . . . C1 C 0.31745(15) 0.31432(15) -0.2414(3) 0.0330(6) Uani 1 1 d . . . C6 C 0.34658(19) 0.25693(17) -0.1893(3) 0.0445(8) Uani 1 1 d . . . H6 H 0.3514 0.2548 -0.1057 0.053 Uiso 1 1 calc R . . C2 C 0.31253(17) 0.31728(17) -0.3672(3) 0.0397(7) Uani 1 1 d . . . H2 H 0.2940 0.3554 -0.4042 0.048 Uiso 1 1 calc R . . C3 C 0.33515(19) 0.2636(2) -0.4370(3) 0.0500(9) Uani 1 1 d . . . H3 H 0.3331 0.2665 -0.5208 0.060 Uiso 1 1 calc R . . C4 C 0.36111(19) 0.20507(19) -0.3823(4) 0.0492(9) Uani 1 1 d . . . C5 C 0.3682(2) 0.20357(19) -0.2584(4) 0.0539(9) Uani 1 1 d . . . H5 H 0.3879 0.1660 -0.2215 0.065 Uiso 1 1 calc R . . N1 N 0.26700(14) 0.42393(13) -0.2047(2) 0.0347(6) Uani 1 1 d . . . H1 H 0.2726 0.4329 -0.2802 0.042 Uiso 1 1 calc R . . O5 O 0.23559(12) 0.46983(11) -0.12898(18) 0.0357(5) Uani 1 1 d . . . O4 O 0.26582(14) 0.38279(14) 0.3292(2) 0.0544(7) Uani 1 1 d . . . C9 C 0.1844(2) 0.29804(19) 0.3571(4) 0.0537(9) Uani 1 1 d . . . H9A H 0.1434 0.2835 0.3180 0.081 Uiso 1 1 calc R . . H9B H 0.1738 0.3162 0.4353 0.081 Uiso 1 1 calc R . . H9C H 0.2145 0.2601 0.3661 0.081 Uiso 1 1 calc R . . N2 N 0.12441(18) 0.35416(19) -0.0481(4) 0.0660(10) Uani 1 1 d U . . H2A H 0.0954 0.3263 -0.0134 0.099 Uiso 1 1 d R . . H2B H 0.0953 0.3815 -0.0824 0.099 Uiso 1 1 d 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 0.0368(2) 0.0355(2) 0.0233(2) 0.00027(12) 0.00042(12) 0.00085(13) O1 0.0458(12) 0.0371(11) 0.0258(10) 0.0034(8) -0.0001(9) 0.0059(9) O3 0.0634(16) 0.0552(15) 0.0357(13) 0.0107(11) -0.0026(11) -0.0144(12) C8 0.0379(16) 0.0317(15) 0.0345(16) 0.0037(12) 0.0068(12) 0.0026(12) C7 0.0316(14) 0.0327(14) 0.0274(14) -0.0005(11) -0.0024(11) -0.0021(11) C1 0.0335(15) 0.0335(15) 0.0319(15) -0.0021(12) -0.0004(12) 0.0007(11) C6 0.057(2) 0.0389(17) 0.0376(17) -0.0006(14) -0.0078(15) 0.0075(15) C2 0.0472(18) 0.0398(17) 0.0321(16) -0.0008(13) -0.0026(13) 0.0056(13) C3 0.055(2) 0.061(2) 0.0345(17) -0.0130(16) -0.0045(15) 0.0106(17) C4 0.0435(19) 0.049(2) 0.055(2) -0.0187(17) -0.0068(16) 0.0081(15) C5 0.061(2) 0.0415(19) 0.059(2) -0.0042(17) -0.0147(19) 0.0175(17) N1 0.0467(15) 0.0371(13) 0.0203(11) -0.0009(10) 0.0026(10) 0.0081(11) O5 0.0475(12) 0.0391(11) 0.0204(9) -0.0033(8) -0.0008(8) 0.0112(9) O4 0.0651(17) 0.0555(15) 0.0425(14) 0.0140(12) -0.0070(12) -0.0237(13) C9 0.059(2) 0.048(2) 0.055(2) 0.0203(17) 0.0020(18) -0.0106(17) N2 0.054(2) 0.064(2) 0.080(3) -0.0319(19) -0.0112(18) 0.0170(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 2.016(2) . ? Zn1 O5 2.049(2) 3 ? Zn1 O4 2.061(2) 4_454 ? Zn1 O5 2.092(2) . ? Zn1 O1 2.110(2) . ? Zn1 N2 2.391(4) . ? O1 C7 1.259(4) . ? O3 C8 1.243(4) . ? C8 O4 1.237(4) . ? C8 C9 1.504(4) . ? C7 N1 1.311(4) . ? C7 C1 1.489(4) . ? C1 C6 1.393(4) . ? C1 C2 1.396(4) . ? C6 C5 1.369(5) . ? C6 H6 0.9300 . ? C2 C3 1.382(5) . ? C2 H2 0.9300 . ? C3 C4 1.400(5) . ? C3 H3 0.9300 . ? C4 C5 1.377(6) . ? C4 N2 1.428(5) 13_554 ? C5 H5 0.9300 . ? N1 O5 1.380(3) . ? N1 H1 0.8600 . ? O5 Zn1 2.049(2) 4_454 ? O4 Zn1 2.061(2) 3 ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? N2 C4 1.428(5) 13_554 ? N2 H2A 0.8812 . ? N2 H2B 0.8731 . ? 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 Zn1 O5 96.59(10) . 3 ? O3 Zn1 O4 92.81(11) . 4_454 ? O5 Zn1 O4 91.40(11) 3 4_454 ? O3 Zn1 O5 169.33(10) . . ? O5 Zn1 O5 89.59(8) 3 . ? O4 Zn1 O5 95.74(9) 4_454 . ? O3 Zn1 O1 93.65(10) . . ? O5 Zn1 O1 99.58(9) 3 . ? O4 Zn1 O1 166.53(10) 4_454 . ? O5 Zn1 O1 76.70(8) . . ? O3 Zn1 N2 80.83(13) . . ? O5 Zn1 N2 172.66(10) 3 . ? O4 Zn1 N2 81.90(12) 4_454 . ? O5 Zn1 N2 94.05(12) . . ? O1 Zn1 N2 87.48(10) . . ? C7 O1 Zn1 111.66(19) . . ? C8 O3 Zn1 138.4(2) . . ? O4 C8 O3 126.1(3) . . ? O4 C8 C9 116.6(3) . . ? O3 C8 C9 117.2(3) . . ? O1 C7 N1 120.3(3) . . ? O1 C7 C1 120.8(3) . . ? N1 C7 C1 118.9(3) . . ? C6 C1 C2 118.4(3) . . ? C6 C1 C7 117.7(3) . . ? C2 C1 C7 123.7(3) . . ? C5 C6 C1 121.4(3) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? C3 C2 C1 120.1(3) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 120.5(3) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 119.0(3) . . ? C5 C4 N2 119.9(4) . 13_554 ? C3 C4 N2 120.9(4) . 13_554 ? C6 C5 C4 120.5(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 N1 O5 118.4(2) . . ? C7 N1 H1 120.8 . . ? O5 N1 H1 120.8 . . ? N1 O5 Zn1 114.50(16) . 4_454 ? N1 O5 Zn1 109.08(16) . . ? Zn1 O5 Zn1 124.23(11) 4_454 . ? C8 O4 Zn1 136.9(2) . 3 ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 N2 Zn1 121.3(2) 13_554 . ? C4 N2 H2A 81.6 13_554 . ? Zn1 N2 H2A 131.1 . . ? C4 N2 H2B 113.6 13_554 . ? Zn1 N2 H2B 107.7 . . ? H2A N2 H2B 98.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Zn1 O1 C7 158.3(2) . . . . ? O5 Zn1 O1 C7 -104.4(2) 3 . . . ? O4 Zn1 O1 C7 39.8(5) 4_454 . . . ? O5 Zn1 O1 C7 -17.1(2) . . . . ? N2 Zn1 O1 C7 77.6(2) . . . . ? O5 Zn1 O3 C8 -6.0(4) 3 . . . ? O4 Zn1 O3 C8 -97.7(4) 4_454 . . . ? O5 Zn1 O3 C8 119.1(5) . . . . ? O1 Zn1 O3 C8 94.1(4) . . . . ? N2 Zn1 O3 C8 -179.0(4) . . . . ? Zn1 O3 C8 O4 -4.5(6) . . . . ? Zn1 O3 C8 C9 176.7(3) . . . . ? Zn1 O1 C7 N1 16.8(4) . . . . ? Zn1 O1 C7 C1 -162.0(2) . . . . ? O1 C7 C1 C6 -8.4(4) . . . . ? N1 C7 C1 C6 172.8(3) . . . . ? O1 C7 C1 C2 166.3(3) . . . . ? N1 C7 C1 C2 -12.4(5) . . . . ? C2 C1 C6 C5 -1.9(6) . . . . ? C7 C1 C6 C5 173.1(3) . . . . ? C6 C1 C2 C3 1.1(5) . . . . ? C7 C1 C2 C3 -173.6(3) . . . . ? C1 C2 C3 C4 2.1(6) . . . . ? C2 C3 C4 C5 -4.5(6) . . . . ? C2 C3 C4 N2 171.0(4) . . . 13_554 ? C1 C6 C5 C4 -0.6(6) . . . . ? C3 C4 C5 C6 3.8(6) . . . . ? N2 C4 C5 C6 -171.8(4) 13_554 . . . ? O1 C7 N1 O5 -3.3(4) . . . . ? C1 C7 N1 O5 175.5(3) . . . . ? C7 N1 O5 Zn1 -156.2(2) . . . 4_454 ? C7 N1 O5 Zn1 -11.9(3) . . . . ? O3 Zn1 O5 N1 -10.9(6) . . . . ? O5 Zn1 O5 N1 114.7(2) 3 . . . ? O4 Zn1 O5 N1 -153.94(19) 4_454 . . . ? O1 Zn1 O5 N1 14.75(18) . . . . ? N2 Zn1 O5 N1 -71.69(19) . . . . ? O3 Zn1 O5 Zn1 129.1(5) . . . 4_454 ? O5 Zn1 O5 Zn1 -105.30(6) 3 . . 4_454 ? O4 Zn1 O5 Zn1 -13.93(15) 4_454 . . 4_454 ? O1 Zn1 O5 Zn1 154.76(14) . . . 4_454 ? N2 Zn1 O5 Zn1 68.32(14) . . . 4_454 ? O3 C8 O4 Zn1 6.3(6) . . . 3 ? C9 C8 O4 Zn1 -174.9(3) . . . 3 ? O3 Zn1 N2 C4 -92.8(4) . . . 13_554 ? O5 Zn1 N2 C4 -162.7(8) 3 . . 13_554 ? O4 Zn1 N2 C4 173.0(4) 4_454 . . 13_554 ? O5 Zn1 N2 C4 77.8(3) . . . 13_554 ? O1 Zn1 N2 C4 1.3(3) . . . 13_554 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O5 0.86 2.20 2.786(3) 124.8 4_454 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.35 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.002 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.084 _database_code_depnum_ccdc_archive 'CCDC 948226' ####################################################################### # # 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_c6992 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '4(C9 H10 N2 O4 Zn), C H4 O' _chemical_formula_sum 'C37 H44 N8 O17 Zn4' _chemical_formula_weight 1134.28 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M 'I 41/a' _symmetry_space_group_name_Hall '-I 4ad' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 19.7648(3) _cell_length_b 19.7648(3) _cell_length_c 11.0481(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4315.91(18) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9946 _cell_measurement_theta_min 2.815 _cell_measurement_theta_max 28.059 _exptl_crystal_description rod _exptl_crystal_colour pink _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.746 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2312 _exptl_absorpt_coefficient_mu 2.280 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5479 _exptl_absorpt_correction_T_max 0.7715 _exptl_absorpt_process_details 'SADABS (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEXII CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30741 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_unetI/netI 0.0127 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 28.29 _reflns_number_total 2687 _reflns_number_gt 2344 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX-II (Bruker, 2005)' _computing_cell_refinement 'SAINT (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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. During the refinement, DFIX restraints were used for reasonable bond distances between O5 and C10. The hydrogen atoms of solvent methanol molecular (O5 and C10) were not abserved nor calculated. ; _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^)+(0.0579P)^2^+8.7049P] 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 2687 _refine_ls_number_parameters 157 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.1005 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.071 _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 Zn1 Zn 0.213089(14) 0.422574(14) 0.03410(2) 0.02752(11) Uani 1 1 d . . . O1 O 0.39380(9) 0.53308(9) 0.20397(15) 0.0316(4) Uani 1 1 d . . . O2 O 0.27968(9) 0.48647(9) 0.12083(15) 0.0306(4) Uani 1 1 d . . . N1 N 0.32620(11) 0.51732(11) 0.04474(17) 0.0311(4) Uani 1 1 d . . . H1 H 0.3178 0.5224 -0.0311 0.037 Uiso 1 1 calc R . . O3 O 0.13275(11) 0.48377(12) 0.0775(2) 0.0489(5) Uani 1 1 d . . . C8 C 0.10167(12) 0.53183(13) 0.0299(2) 0.0313(5) Uani 1 1 d . . . C7 C 0.38336(12) 0.53850(12) 0.0916(2) 0.0270(4) Uani 1 1 d . . . C1 C 0.43568(12) 0.56732(12) 0.0099(2) 0.0280(5) Uani 1 1 d . . . N2 N 0.60514(15) 0.62486(14) -0.1977(3) 0.0538(7) Uani 1 1 d . . . H2A H 0.6413 0.6386 -0.1620 0.065 Uiso 1 1 calc R . . H2B H 0.6045 0.6203 -0.2751 0.065 Uiso 1 1 calc R . . C4 C 0.54655(14) 0.60969(14) -0.1290(3) 0.0399(6) Uani 1 1 d . . . C2 C 0.49251(13) 0.59578(14) 0.0637(3) 0.0373(6) Uani 1 1 d . . . H2 H 0.4938 0.6008 0.1474 0.045 Uiso 1 1 calc R . . C6 C 0.43326(14) 0.56290(14) -0.1163(2) 0.0346(5) Uani 1 1 d . . . H6 H 0.3951 0.5452 -0.1542 0.041 Uiso 1 1 calc R . . C5 C 0.48783(15) 0.58491(15) -0.1851(3) 0.0404(6) Uani 1 1 d . . . H5 H 0.4854 0.5832 -0.2692 0.048 Uiso 1 1 calc R . . C3 C 0.54734(15) 0.61685(16) -0.0050(3) 0.0454(7) Uani 1 1 d . . . H3 H 0.5848 0.6359 0.0329 0.055 Uiso 1 1 calc R . . C9 C 0.04789(16) 0.56606(17) 0.1053(3) 0.0488(7) Uani 1 1 d . . . H9A H 0.0662 0.6063 0.1412 0.073 Uiso 1 1 calc R . . H9B H 0.0331 0.5358 0.1680 0.073 Uiso 1 1 calc R . . H9C H 0.0102 0.5778 0.0547 0.073 Uiso 1 1 calc R . . O4 O 0.11071(11) 0.55471(12) -0.07353(18) 0.0474(5) Uani 1 1 d . . . C10 C 0.5000 0.7500 -0.3750 0.186(9) Uani 1 4 d SD . 1 O5 O 0.5315(17) 0.6912(8) -0.411(2) 0.219(16) Uani 0.25 1 d PD A 1 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 0.03071(17) 0.03161(17) 0.02025(16) 0.00053(9) 0.00093(9) 0.00034(10) O1 0.0329(9) 0.0393(9) 0.0227(8) 0.0004(7) -0.0016(6) -0.0046(7) O2 0.0302(8) 0.0417(9) 0.0198(7) -0.0025(7) 0.0035(6) -0.0095(7) N1 0.0338(10) 0.0411(11) 0.0184(9) 0.0023(8) 0.0001(7) -0.0095(8) O3 0.0495(12) 0.0557(13) 0.0415(11) 0.0053(10) 0.0116(9) 0.0197(10) C8 0.0265(11) 0.0355(12) 0.0320(12) -0.0072(9) 0.0041(9) -0.0029(9) C7 0.0273(11) 0.0274(11) 0.0263(11) -0.0015(8) 0.0005(8) 0.0015(8) C1 0.0290(11) 0.0286(11) 0.0263(11) 0.0003(8) 0.0015(9) -0.0008(9) N2 0.0502(15) 0.0513(15) 0.0598(17) -0.0063(13) 0.0245(13) -0.0122(12) C4 0.0399(14) 0.0339(13) 0.0460(16) -0.0013(11) 0.0148(12) -0.0048(11) C2 0.0344(13) 0.0462(15) 0.0312(13) -0.0037(11) -0.0014(10) -0.0066(11) C6 0.0365(13) 0.0391(13) 0.0282(12) -0.0007(10) -0.0002(10) -0.0051(10) C5 0.0498(16) 0.0439(15) 0.0274(12) -0.0015(11) 0.0067(11) -0.0079(12) C3 0.0368(14) 0.0514(17) 0.0481(16) -0.0083(13) 0.0024(12) -0.0144(12) C9 0.0449(16) 0.0540(18) 0.0476(17) -0.0020(13) 0.0182(13) 0.0116(13) O4 0.0538(12) 0.0597(13) 0.0288(10) 0.0023(9) 0.0114(9) 0.0153(10) C10 0.180(13) 0.180(13) 0.20(2) 0.000 0.000 0.000 O5 0.31(4) 0.18(3) 0.17(2) 0.04(2) 0.17(3) 0.03(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O4 2.023(2) 3 ? Zn1 O3 2.053(2) . ? Zn1 O2 2.0604(17) . ? Zn1 O2 2.0875(17) 4_454 ? Zn1 O1 2.1021(18) 4_454 ? Zn1 N2 2.389(3) 16_655 ? O1 C7 1.263(3) . ? O1 Zn1 2.1021(18) 3 ? O2 N1 1.387(3) . ? O2 Zn1 2.0875(17) 3 ? N1 C7 1.311(3) . ? N1 H1 0.8600 . ? O3 C8 1.247(3) . ? C8 O4 1.242(3) . ? C8 C9 1.510(4) . ? C7 C1 1.486(3) . ? C1 C2 1.390(3) . ? C1 C6 1.397(3) . ? N2 C4 1.417(4) . ? N2 Zn1 2.389(3) 11_665 ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? C4 C3 1.377(4) . ? C4 C5 1.404(4) . ? C2 C3 1.387(4) . ? C2 H2 0.9300 . ? C6 C5 1.390(4) . ? C6 H6 0.9300 . ? C5 H5 0.9300 . ? C3 H3 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? O4 Zn1 2.023(2) 4_454 ? C10 O5 1.379(10) 15_564 ? C10 O5 1.379(10) 6_564 ? C10 O5 1.379(10) . ? C10 O5 1.379(10) 12_765 ? 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 O4 Zn1 O3 92.29(9) 3 . ? O4 Zn1 O2 96.89(8) 3 . ? O3 Zn1 O2 91.40(9) . . ? O4 Zn1 O2 169.58(8) 3 4_454 ? O3 Zn1 O2 96.13(8) . 4_454 ? O2 Zn1 O2 89.05(6) . 4_454 ? O4 Zn1 O1 93.71(8) 3 4_454 ? O3 Zn1 O1 167.20(8) . 4_454 ? O2 Zn1 O1 99.09(7) . 4_454 ? O2 Zn1 O1 76.85(6) 4_454 4_454 ? O4 Zn1 N2 81.19(10) 3 16_655 ? O3 Zn1 N2 81.91(9) . 16_655 ? O2 Zn1 N2 172.93(8) . 16_655 ? O2 Zn1 N2 93.90(10) 4_454 16_655 ? O1 Zn1 N2 87.85(8) 4_454 16_655 ? C7 O1 Zn1 111.58(15) . 3 ? N1 O2 Zn1 114.27(13) . . ? N1 O2 Zn1 108.75(13) . 3 ? Zn1 O2 Zn1 123.71(9) . 3 ? C7 N1 O2 118.18(19) . . ? C7 N1 H1 120.9 . . ? O2 N1 H1 120.9 . . ? C8 O3 Zn1 136.99(19) . . ? O4 C8 O3 126.4(2) . . ? O4 C8 C9 116.5(3) . . ? O3 C8 C9 117.1(2) . . ? O1 C7 N1 120.1(2) . . ? O1 C7 C1 121.0(2) . . ? N1 C7 C1 118.8(2) . . ? C2 C1 C6 118.7(2) . . ? C2 C1 C7 117.2(2) . . ? C6 C1 C7 123.9(2) . . ? C4 N2 Zn1 121.07(19) . 11_665 ? C4 N2 H2A 120.0 . . ? Zn1 N2 H2A 87.1 11_665 . ? C4 N2 H2B 120.0 . . ? Zn1 N2 H2B 62.3 11_665 . ? H2A N2 H2B 120.0 . . ? C3 C4 C5 119.0(2) . . ? C3 C4 N2 120.1(3) . . ? C5 C4 N2 120.8(3) . . ? C3 C2 C1 121.3(3) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C5 C6 C1 120.0(2) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? C6 C5 C4 120.6(3) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 O4 Zn1 137.65(19) . 4_454 ? O5 C10 O5 94.9(7) 15_564 6_564 ? O5 C10 O5 94.9(7) 15_564 . ? O5 C10 O5 146(2) 6_564 . ? O5 C10 O5 146(2) 15_564 12_765 ? O5 C10 O5 94.9(7) 6_564 12_765 ? O5 C10 O5 94.9(7) . 12_765 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Zn1 O2 N1 152.52(17) 3 . . . ? O3 Zn1 O2 N1 -115.00(16) . . . . ? O2 Zn1 O2 N1 -18.90(15) 4_454 . . . ? O1 Zn1 O2 N1 57.63(16) 4_454 . . . ? N2 Zn1 O2 N1 -133.7(8) 16_655 . . . ? O4 Zn1 O2 Zn1 16.08(12) 3 . . 3 ? O3 Zn1 O2 Zn1 108.56(11) . . . 3 ? O2 Zn1 O2 Zn1 -155.34(9) 4_454 . . 3 ? O1 Zn1 O2 Zn1 -78.81(10) 4_454 . . 3 ? N2 Zn1 O2 Zn1 89.9(8) 16_655 . . 3 ? Zn1 O2 N1 C7 -156.25(18) . . . . ? Zn1 O2 N1 C7 -13.5(3) 3 . . . ? O4 Zn1 O3 C8 -170.9(3) 3 . . . ? O2 Zn1 O3 C8 92.2(3) . . . . ? O2 Zn1 O3 C8 3.0(3) 4_454 . . . ? O1 Zn1 O3 C8 -52.9(6) 4_454 . . . ? N2 Zn1 O3 C8 -90.1(3) 16_655 . . . ? Zn1 O3 C8 O4 5.6(5) . . . . ? Zn1 O3 C8 C9 -174.1(2) . . . . ? Zn1 O1 C7 N1 17.8(3) 3 . . . ? Zn1 O1 C7 C1 -160.85(17) 3 . . . ? O2 N1 C7 O1 -2.8(3) . . . . ? O2 N1 C7 C1 175.8(2) . . . . ? O1 C7 C1 C2 -8.0(3) . . . . ? N1 C7 C1 C2 173.4(2) . . . . ? O1 C7 C1 C6 167.1(2) . . . . ? N1 C7 C1 C6 -11.6(4) . . . . ? Zn1 N2 C4 C3 106.2(3) 11_665 . . . ? Zn1 N2 C4 C5 -71.5(4) 11_665 . . . ? C6 C1 C2 C3 -2.8(4) . . . . ? C7 C1 C2 C3 172.5(3) . . . . ? C2 C1 C6 C5 1.9(4) . . . . ? C7 C1 C6 C5 -173.1(2) . . . . ? C1 C6 C5 C4 2.0(4) . . . . ? C3 C4 C5 C6 -5.0(4) . . . . ? N2 C4 C5 C6 172.7(3) . . . . ? C5 C4 C3 C2 4.1(5) . . . . ? N2 C4 C3 C2 -173.6(3) . . . . ? C1 C2 C3 C4 -0.2(5) . . . . ? O3 C8 O4 Zn1 -1.8(5) . . . 4_454 ? C9 C8 O4 Zn1 177.9(2) . . . 4_454 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.877 _refine_diff_density_min -0.395 _refine_diff_density_rms 0.084 _database_code_depnum_ccdc_archive 'CCDC 948228'