# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N8 O6 Zn' _chemical_formula_sum 'C14 H18 N8 O6 Zn' _chemical_formula_weight 459.73 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 orthorhombic _symmetry_space_group_name_H-M 'P bcn ' _symmetry_space_group_name_Hall '-P 2n 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.1313(18) _cell_length_b 8.1896(16) _cell_length_c 24.073(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1800.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13707 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 27.73 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.696 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 1.419 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7007 _exptl_absorpt_correction_T_max 0.7093 _exptl_absorpt_process_details Higashi,1995 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku SCXmini diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14135 _diffrn_reflns_av_R_equivalents 0.0840 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 25.18 _reflns_number_total 1621 _reflns_number_gt 1304 _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^)+(0.0247P)^2^+14.6510P] 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 1621 _refine_ls_number_parameters 140 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0873 _refine_ls_R_factor_gt 0.0664 _refine_ls_wR_factor_ref 0.1326 _refine_ls_wR_factor_gt 0.1227 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.003 _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 0.5000 0.19515(12) 0.2500 0.0278(3) Uani 1 2 d SD . . N1 N 0.3517(5) 0.2996(6) 0.20365(18) 0.0255(10) Uani 1 1 d . . . C2 C 0.2575(6) 0.4383(7) 0.1327(2) 0.0273(12) Uani 1 1 d . . . O1W O 0.4062(4) 0.0360(6) 0.30253(19) 0.0417(11) Uani 1 1 d D . . C1 C 0.2049(6) 0.2896(7) 0.2014(2) 0.0299(13) Uani 1 1 d . . . H1 H 0.1509 0.2304 0.2272 0.036 Uiso 1 1 calc R . . N3 N 0.2555(6) 0.5361(6) 0.08629(18) 0.0325(11) Uani 1 1 d . . . N2 N 0.1412(5) 0.3710(6) 0.15913(19) 0.0279(11) Uani 1 1 d . . . O1 O 0.3884(5) 0.6828(6) 0.02421(18) 0.0512(12) Uani 1 1 d . . . C3 C 0.3855(6) 0.3979(7) 0.1588(2) 0.0239(12) Uani 1 1 d . . . O2 O 0.6400(4) 0.4363(6) 0.16632(19) 0.0465(12) Uani 1 1 d . . . N4 N 0.5147(5) 0.5580(6) 0.09464(19) 0.0347(11) Uani 1 1 d . . . C4 C 0.5227(6) 0.4605(7) 0.1423(2) 0.0304(13) Uani 1 1 d . . . C5 C 0.3847(7) 0.5980(8) 0.0654(2) 0.0340(14) Uani 1 1 d . . . C6 C 0.1181(7) 0.5754(8) 0.0582(3) 0.0459(18) Uani 1 1 d . . . H6A H 0.1292 0.6755 0.0378 0.069 Uiso 1 1 calc R . . H6B H 0.0416 0.5877 0.0852 0.069 Uiso 1 1 calc R . . H6C H 0.0931 0.4889 0.0330 0.069 Uiso 1 1 calc R . . C7 C 0.6503(7) 0.6322(9) 0.0740(3) 0.053(2) Uani 1 1 d . . . H7A H 0.7326 0.5692 0.0865 0.080 Uiso 1 1 calc R . . H7B H 0.6583 0.7417 0.0879 0.080 Uiso 1 1 calc R . . H7C H 0.6487 0.6343 0.0342 0.080 Uiso 1 1 calc R . . H1WB H 0.451(4) -0.041(7) 0.319(3) 0.080 Uiso 1 1 d D . . H1WA H 0.320(3) 0.037(7) 0.314(3) 0.080 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0188(4) 0.0340(5) 0.0306(5) 0.000 -0.0050(4) 0.000 N1 0.020(2) 0.030(3) 0.027(2) 0.001(2) -0.0030(19) -0.001(2) C2 0.023(3) 0.028(3) 0.031(3) -0.008(3) -0.007(3) 0.005(2) O1W 0.019(2) 0.052(3) 0.054(3) 0.024(2) 0.004(2) 0.000(2) C1 0.022(3) 0.040(3) 0.028(3) -0.007(3) 0.001(2) 0.002(3) N3 0.032(3) 0.035(3) 0.031(2) 0.002(2) -0.013(2) 0.004(2) N2 0.014(2) 0.035(3) 0.034(3) -0.006(2) -0.005(2) 0.005(2) O1 0.063(3) 0.051(3) 0.040(2) 0.015(2) -0.007(2) -0.001(3) C3 0.020(3) 0.023(3) 0.028(3) -0.003(2) -0.004(2) 0.002(2) O2 0.021(2) 0.062(3) 0.056(3) 0.012(2) -0.013(2) -0.011(2) N4 0.030(3) 0.039(3) 0.035(3) 0.004(2) -0.002(2) -0.005(2) C4 0.026(3) 0.035(3) 0.030(3) -0.002(2) -0.001(3) -0.001(3) C5 0.045(4) 0.030(3) 0.027(3) -0.003(3) -0.010(3) 0.004(3) C6 0.041(4) 0.042(4) 0.055(4) 0.004(3) -0.025(3) 0.006(3) C7 0.040(4) 0.054(5) 0.065(5) 0.013(4) 0.002(4) -0.015(4) _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 1.952(4) 3_655 ? Zn1 N1 1.952(4) . ? Zn1 O1W 2.008(4) 3_655 ? Zn1 O1W 2.008(4) . ? N1 C1 1.344(7) . ? N1 C3 1.382(7) . ? C2 N2 1.355(7) . ? C2 C3 1.368(7) . ? C2 N3 1.375(7) . ? C1 N2 1.348(7) . ? N3 C5 1.379(8) . ? N3 C6 1.462(7) . ? O1 C5 1.211(7) . ? C3 C4 1.411(7) . ? O2 C4 1.233(7) . ? N4 C4 1.399(7) . ? N4 C5 1.419(7) . ? N4 C7 1.466(8) . ? 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 N1 128.0(3) 3_655 . ? N1 Zn1 O1W 110.39(17) 3_655 3_655 ? N1 Zn1 O1W 102.73(19) . 3_655 ? N1 Zn1 O1W 102.73(19) 3_655 . ? N1 Zn1 O1W 110.39(17) . . ? O1W Zn1 O1W 99.1(3) 3_655 . ? C1 N1 C3 103.1(4) . . ? C1 N1 Zn1 133.5(4) . . ? C3 N1 Zn1 123.2(3) . . ? N2 C2 C3 110.9(5) . . ? N2 C2 N3 127.4(5) . . ? C3 C2 N3 121.7(5) . . ? N1 C1 N2 115.6(5) . . ? C2 N3 C5 120.0(5) . . ? C2 N3 C6 121.1(5) . . ? C5 N3 C6 119.0(5) . . ? C1 N2 C2 102.5(4) . . ? C2 C3 N1 108.0(5) . . ? C2 C3 C4 122.8(5) . . ? N1 C3 C4 129.1(5) . . ? C4 N4 C5 125.7(5) . . ? C4 N4 C7 118.0(5) . . ? C5 N4 C7 116.3(5) . . ? O2 C4 N4 121.5(5) . . ? O2 C4 C3 125.5(5) . . ? N4 C4 C3 113.1(5) . . ? O1 C5 N3 122.3(6) . . ? O1 C5 N4 121.0(6) . . ? N3 C5 N4 116.7(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O2 0.834(19) 1.90(3) 2.671(5) 153(6) 6_556 O1W H1WB N2 0.86(2) 1.95(3) 2.699(6) 146(4) 6_656 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.18 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.681 _refine_diff_density_min -0.446 _refine_diff_density_rms 0.080 _database_code_depnum_ccdc_archive 'CCDC 914057' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H12 N4 O8 Zn2' _chemical_formula_sum 'C11 H12 N4 O8 Zn2' _chemical_formula_weight 458.99 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 triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8873(16) _cell_length_b 8.7132(17) _cell_length_c 11.451(2) _cell_angle_alpha 83.47(3) _cell_angle_beta 80.19(3) _cell_angle_gamma 73.05(3) _cell_volume 740.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6464 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 27.55 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.060 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 3.295 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4699 _exptl_absorpt_correction_T_max 0.5052 _exptl_absorpt_process_details Higashi,1995 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku SCXmini diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7771 _diffrn_reflns_av_R_equivalents 0.0808 _diffrn_reflns_av_sigmaI/netI 0.1160 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3381 _reflns_number_gt 2105 _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^)+(0.0266P)^2^+12.4004P] 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 3381 _refine_ls_number_parameters 240 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1345 _refine_ls_R_factor_gt 0.0736 _refine_ls_wR_factor_ref 0.1758 _refine_ls_wR_factor_gt 0.1543 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.005 _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 O6 O 0.6887(10) 0.1692(8) 0.4459(6) 0.0401(18) Uani 1 1 d . . . O5 O 0.9017(10) 0.0340(8) 0.2199(5) 0.0351(17) Uani 1 1 d . . . N2 N 0.8735(10) 0.5262(9) 0.6844(6) 0.0264(17) Uani 1 1 d . . . Zn1 Zn 1.03704(15) 0.28181(12) 0.31539(9) 0.0251(3) Uani 1 1 d . . . Zn2 Zn 1.09060(17) 0.03459(12) 0.60181(9) 0.0319(3) Uani 1 1 d D . . O3 O 1.0594(9) 0.2141(8) 0.1558(5) 0.0305(15) Uani 1 1 d . . . O7 O 1.1047(10) 0.0836(8) 0.4178(6) 0.0312(16) Uani 1 1 d D . . O2 O 0.6193(10) 0.1028(8) 0.7381(6) 0.0407(18) Uani 1 1 d . . . O4 O 0.7876(9) 0.3832(8) 0.3766(6) 0.0381(17) Uani 1 1 d . . . C3 C 0.7592(13) 0.3156(10) 0.7201(8) 0.024(2) Uani 1 1 d . . . N1 N 0.9239(11) 0.2630(8) 0.6482(6) 0.0261(17) Uani 1 1 d . . . O1W O 1.3406(11) 0.1214(9) 0.5985(8) 0.046(2) Uani 1 1 d D . . N4 N 0.4723(11) 0.3342(10) 0.8308(7) 0.0331(19) Uani 1 1 d . . . N3 N 0.5779(10) 0.5663(9) 0.8013(7) 0.0297(18) Uani 1 1 d . . . C9 C 0.5090(14) 0.4251(12) 0.4961(9) 0.034(2) Uani 1 1 d . . . H9 H 0.4150 0.3829 0.5301 0.041 Uiso 1 1 calc R . . C2 C 0.7321(13) 0.4754(11) 0.7387(8) 0.026(2) Uani 1 1 d . . . C4 C 0.6192(14) 0.2401(12) 0.7603(8) 0.032(2) Uani 1 1 d . . . C10 C 0.9829(12) 0.1086(11) 0.1407(8) 0.027(2) Uani 1 1 d . . . O1 O 0.3152(10) 0.5657(10) 0.9209(7) 0.054(2) Uani 1 1 d . . . C1 C 0.9844(13) 0.3914(10) 0.6318(8) 0.026(2) Uani 1 1 d . . . H1 H 1.0950 0.3906 0.5875 0.031 Uiso 1 1 calc R . . C5 C 0.4452(15) 0.4949(13) 0.8557(10) 0.037(2) Uani 1 1 d . . . C11 C 0.9997(14) 0.0696(11) 0.0153(8) 0.031(2) Uani 1 1 d . . . H11 H 1.0105 0.1493 -0.0445 0.037 Uiso 1 1 calc R . . C8 C 0.6749(14) 0.3160(11) 0.4347(9) 0.031(2) Uani 1 1 d . . . C6 C 0.5486(14) 0.7379(12) 0.8133(11) 0.045(3) Uani 1 1 d . . . H6C H 0.6398 0.7523 0.8533 0.068 Uiso 1 1 calc R . . H6B H 0.4332 0.7807 0.8585 0.068 Uiso 1 1 calc R . . H6A H 0.5537 0.7933 0.7359 0.068 Uiso 1 1 calc R . . C7 C 0.3227(16) 0.2655(16) 0.8781(11) 0.056(3) Uani 1 1 d . . . H7A H 0.2566 0.2643 0.8153 0.084 Uiso 1 1 calc R . . H7C H 0.2450 0.3296 0.9393 0.084 Uiso 1 1 calc R . . H7B H 0.3688 0.1576 0.9106 0.084 Uiso 1 1 calc R . . H7 H 1.189(12) 0.033(13) 0.369(9) 0.07(5) Uiso 1 1 d D . . H1WA H 1.390(10) 0.104(19) 0.662(4) 0.13(8) Uiso 1 1 d D . . H1WB H 1.424(8) 0.099(14) 0.540(5) 0.06(4) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O6 0.052(5) 0.027(4) 0.043(4) -0.004(3) -0.003(4) -0.015(4) O5 0.054(5) 0.041(4) 0.017(3) 0.002(3) -0.004(3) -0.026(4) N2 0.033(5) 0.022(4) 0.026(4) -0.003(3) 0.000(3) -0.012(4) Zn1 0.0348(7) 0.0188(5) 0.0236(6) -0.0032(4) -0.0026(5) -0.0105(5) Zn2 0.0544(9) 0.0184(6) 0.0226(6) -0.0036(5) -0.0048(6) -0.0091(6) O3 0.039(4) 0.033(4) 0.025(3) -0.010(3) -0.004(3) -0.018(3) O7 0.049(5) 0.027(4) 0.020(3) -0.002(3) -0.006(3) -0.013(3) O2 0.052(5) 0.028(4) 0.047(4) -0.010(3) 0.002(4) -0.021(4) O4 0.035(4) 0.029(4) 0.048(4) -0.002(3) 0.001(3) -0.009(3) C3 0.032(5) 0.022(5) 0.023(5) -0.002(4) -0.005(4) -0.012(4) N1 0.038(5) 0.018(4) 0.025(4) -0.006(3) -0.003(4) -0.012(4) O1W 0.058(5) 0.038(5) 0.049(5) -0.003(4) -0.005(5) -0.024(4) N4 0.030(5) 0.041(5) 0.031(4) -0.005(4) 0.001(4) -0.017(4) N3 0.028(5) 0.024(4) 0.038(5) -0.009(4) -0.003(4) -0.006(4) C9 0.033(6) 0.040(6) 0.032(5) 0.002(5) 0.002(4) -0.019(5) C2 0.037(6) 0.028(5) 0.017(4) -0.005(4) -0.006(4) -0.013(5) C4 0.041(6) 0.037(6) 0.021(5) -0.002(4) -0.007(4) -0.014(5) C10 0.026(5) 0.028(5) 0.028(5) -0.008(4) -0.002(4) -0.007(4) O1 0.037(5) 0.057(5) 0.064(5) -0.027(4) 0.013(4) -0.009(4) C1 0.039(6) 0.017(4) 0.024(5) -0.006(4) -0.004(4) -0.012(4) C5 0.036(6) 0.035(6) 0.045(6) -0.008(5) -0.004(5) -0.013(5) C11 0.043(6) 0.031(5) 0.022(5) 0.001(4) -0.001(4) -0.017(5) C8 0.036(6) 0.025(5) 0.037(6) 0.001(4) -0.013(5) -0.012(5) C6 0.035(7) 0.027(6) 0.074(8) -0.029(6) -0.006(6) 0.001(5) C7 0.052(8) 0.069(9) 0.057(8) -0.018(7) 0.012(6) -0.039(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 O6 C8 1.245(11) . ? O6 Zn2 2.139(7) 2_756 ? O5 C10 1.251(10) . ? O5 Zn2 2.067(6) 2_756 ? N2 C2 1.348(11) . ? N2 C1 1.374(11) . ? N2 Zn1 1.996(7) 2_766 ? Zn1 O3 1.948(6) . ? Zn1 O4 1.949(7) . ? Zn1 O7 1.964(7) . ? Zn1 N2 1.996(7) 2_766 ? Zn2 O5 2.067(6) 2_756 ? Zn2 O7 2.092(6) . ? Zn2 N1 2.109(7) . ? Zn2 O6 2.139(7) 2_756 ? Zn2 O7 2.140(7) 2_756 ? Zn2 O1W 2.302(8) . ? Zn2 Zn2 3.130(2) 2_756 ? O3 C10 1.278(10) . ? O7 Zn2 2.140(7) 2_756 ? O2 C4 1.250(11) . ? O4 C8 1.260(11) . ? C3 C2 1.381(12) . ? C3 N1 1.396(11) . ? C3 C4 1.430(13) . ? N1 C1 1.322(11) . ? N4 C4 1.394(12) . ? N4 C5 1.408(13) . ? N4 C7 1.472(13) . ? N3 C2 1.375(12) . ? N3 C5 1.393(12) . ? N3 C6 1.464(11) . ? C9 C9 1.282(19) 2_666 ? C9 C8 1.491(14) . ? C10 C11 1.489(12) . ? O1 C5 1.210(12) . ? C11 C11 1.299(18) 2_755 ? 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 C8 O6 Zn2 131.5(7) . 2_756 ? C10 O5 Zn2 136.4(6) . 2_756 ? C2 N2 C1 102.7(7) . . ? C2 N2 Zn1 137.1(6) . 2_766 ? C1 N2 Zn1 119.5(6) . 2_766 ? O3 Zn1 O4 111.0(3) . . ? O3 Zn1 O7 106.1(3) . . ? O4 Zn1 O7 104.7(3) . . ? O3 Zn1 N2 112.2(3) . 2_766 ? O4 Zn1 N2 96.9(3) . 2_766 ? O7 Zn1 N2 124.9(3) . 2_766 ? O5 Zn2 O7 174.2(3) 2_756 . ? O5 Zn2 N1 89.3(3) 2_756 . ? O7 Zn2 N1 96.3(3) . . ? O5 Zn2 O6 90.8(3) 2_756 2_756 ? O7 Zn2 O6 83.5(3) . 2_756 ? N1 Zn2 O6 165.8(3) . 2_756 ? O5 Zn2 O7 95.8(3) 2_756 2_756 ? O7 Zn2 O7 84.6(3) . 2_756 ? N1 Zn2 O7 100.8(3) . 2_756 ? O6 Zn2 O7 93.4(3) 2_756 2_756 ? O5 Zn2 O1W 88.5(3) 2_756 . ? O7 Zn2 O1W 90.0(3) . . ? N1 Zn2 O1W 90.3(3) . . ? O6 Zn2 O1W 75.4(3) 2_756 . ? O7 Zn2 O1W 168.1(3) 2_756 . ? O5 Zn2 Zn2 137.25(19) 2_756 2_756 ? O7 Zn2 Zn2 42.89(19) . 2_756 ? N1 Zn2 Zn2 101.6(2) . 2_756 ? O6 Zn2 Zn2 88.0(2) 2_756 2_756 ? O7 Zn2 Zn2 41.71(17) 2_756 2_756 ? O1W Zn2 Zn2 132.0(2) . 2_756 ? C10 O3 Zn1 118.6(6) . . ? Zn1 O7 Zn2 133.7(3) . . ? Zn1 O7 Zn2 102.2(3) . 2_756 ? Zn2 O7 Zn2 95.4(3) . 2_756 ? C8 O4 Zn1 127.5(6) . . ? C2 C3 N1 108.1(8) . . ? C2 C3 C4 120.0(9) . . ? N1 C3 C4 131.4(8) . . ? C1 N1 C3 103.1(7) . . ? C1 N1 Zn2 121.5(6) . . ? C3 N1 Zn2 133.8(6) . . ? C4 N4 C5 126.6(8) . . ? C4 N4 C7 117.9(9) . . ? C5 N4 C7 115.3(9) . . ? C2 N3 C5 119.9(8) . . ? C2 N3 C6 121.7(8) . . ? C5 N3 C6 118.4(8) . . ? C9 C9 C8 122.6(12) 2_666 . ? N2 C2 N3 126.6(8) . . ? N2 C2 C3 110.3(8) . . ? N3 C2 C3 123.0(8) . . ? O2 C4 N4 119.8(9) . . ? O2 C4 C3 126.2(9) . . ? N4 C4 C3 114.0(8) . . ? O5 C10 O3 126.8(8) . . ? O5 C10 C11 118.1(8) . . ? O3 C10 C11 115.0(8) . . ? N1 C1 N2 115.8(8) . . ? O1 C5 N3 122.3(9) . . ? O1 C5 N4 121.9(10) . . ? N3 C5 N4 115.8(9) . . ? C11 C11 C10 123.7(11) 2_755 . ? O6 C8 O4 126.7(10) . . ? O6 C8 C9 117.4(9) . . ? O4 C8 C9 115.9(8) . . ? 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 O1W H1WB O6 0.85(2) 2.39(6) 3.104(11) 142(7) 1_655 O1W H1WA O2 0.86(2) 2.14(4) 2.889(12) 146(6) 1_655 O7 H7 O2 0.84(2) 1.96(3) 2.799(10) 175(13) 2_756 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.614 _refine_diff_density_min -0.914 _refine_diff_density_rms 0.138 #===END _database_code_depnum_ccdc_archive 'CCDC 914058'