# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof. Roland Fischer' _publ_contact_author_email roland.fischer@rub.de _publ_section_title ; Zinc-1,4-Benzenedicarboxylate-Bipyridine Frameworks - Linker Functionalization Impacts Network Topology During Solvothermal Synthesis ; loop_ _publ_author_name S.Henke A.Schneemann S.Kapoor R.Winter R.Fischer # Attachment '- 2,3-BME-BMOF_mit text.cif' data_2,3-BME-BMOF _database_code_depnum_ccdc_archive 'CCDC 834509' #TrackingRef '- 2,3-BME-BMOF_mit text.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H20 N O8 Zn' _chemical_formula_weight 455.73 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 tetragonal _symmetry_space_group_name_H-M P4/mmm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, x, z' 'y, -x, z' '-x, y, -z' 'x, -y, -z' 'y, x, -z' '-y, -x, -z' '-x, -y, -z' 'x, y, -z' 'y, -x, -z' '-y, x, -z' 'x, -y, z' '-x, y, z' '-y, -x, z' 'y, x, z' _cell_length_a 10.773(4) _cell_length_b 10.773(4) _cell_length_c 13.947(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1618.6(10) _cell_formula_units_Z 2 _cell_measurement_temperature 108(2) _cell_measurement_reflns_used 551 _cell_measurement_theta_min 3.0409 _cell_measurement_theta_max 28.7766 _exptl_crystal_description 'block shaped' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.936 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 470 _exptl_absorpt_coefficient_mu 0.788 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.40719 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 108(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.4171 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6647 _diffrn_reflns_av_R_equivalents 0.1752 _diffrn_reflns_av_sigmaI/netI 0.1327 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 24.99 _reflns_number_total 885 _reflns_number_gt 519 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlisPro, Oxford Diffraction Ltd.' _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. The used crystal was of very weak diffraction quality. The entire 2,3-BME-bdc linker is disordered over two positions. Furthermore, the phenyl rings are tilted from the ideal plane, which is defined by the carboxylate groups, due to the substitution pattern of the linker. Therefore, the phenyl rings are disordered over four positions, which makes it impossible to localize the attached flexible 2-methoxyethoxy chains. In addition the bipy linker is disordered over four positions by symmetry. All atoms were refined anisotropically. Because of the high disorder of the hydrogen containing groups of the material hydrogen atoms were not added to the model structure. The atoms of the flexible (-O-CH2-CH2-O-CH3) side chains and the DMF/EtOH molecules placed in the pores could not be located in the diffraction experiment, due to very high disorder. However, the atoms of the 2-methoxyethoxy substituents were included in the empirical formula and formula weight. The residual electron density in the solvent accessible ; _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens none _refine_ls_hydrogen_treatment none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 885 _refine_ls_number_parameters 73 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.0873 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0663 _refine_ls_wR_factor_gt 0.0520 _refine_ls_goodness_of_fit_ref 0.658 _refine_ls_restrained_S_all 0.651 _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 C5A C 0.5806(8) 0.5806(8) 0.8928(8) 0.033(3) Uani 0.25 2 d SPU . . C4A C 0.5778(12) 0.5778(12) 0.8022(11) 0.066(4) Uani 0.25 2 d SPU . . C3 C 0.0618(11) 0.477(2) 0.4240(7) 0.044(7) Uani 0.25 1 d PU . . C3A C 0.0584(12) 0.3889(11) 0.4229(9) 0.076(5) Uani 0.25 1 d PU . . C2 C 0.1274(9) 0.5517(7) 0.5000 0.081(4) Uani 0.50 2 d SPU . . N1 N 0.5000 0.5000 0.7482(3) 0.0475(16) Uani 1 8 d S . . Zn1 Zn 0.5000 0.5000 0.60443(5) 0.0560(3) Uani 1 8 d S . . O1 O 0.3230(3) 0.4593(4) 0.57790(15) 0.0645(18) Uani 0.50 1 d P . . C1 C 0.2714(8) 0.5441(8) 0.5000 0.073(4) Uani 0.50 2 d SPU . . C6 C 0.5000 0.5000 0.9495(3) 0.059(2) Uani 1 8 d S . . C5 C 0.6246(10) 0.5000 0.8944(7) 0.016(2) Uani 0.25 2 d SPU . . C4 C 0.6186(14) 0.5000 0.8014(9) 0.037(4) Uani 0.25 2 d SPU . . 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 C5A 0.038(3) 0.038(3) 0.024(4) -0.004(3) -0.004(3) -0.013(4) C4A 0.069(5) 0.069(5) 0.058(6) -0.001(3) -0.001(3) 0.002(5) C3 0.074(7) 0.02(2) 0.040(4) -0.006(6) -0.004(3) -0.002(7) C3A 0.069(9) 0.081(12) 0.079(8) -0.019(8) -0.006(5) -0.027(9) C2 0.105(7) 0.105(10) 0.032(4) 0.000 0.000 0.008(6) N1 0.057(3) 0.057(3) 0.028(3) 0.000 0.000 0.000 Zn1 0.0736(5) 0.0736(5) 0.0209(4) 0.000 0.000 0.000 O1 0.062(2) 0.100(5) 0.0308(14) 0.0105(16) -0.0121(14) -0.023(2) C1 0.071(6) 0.109(12) 0.039(4) 0.000 0.000 0.019(5) C6 0.080(4) 0.080(4) 0.018(3) 0.000 0.000 0.000 C5 0.019(4) 0.010(4) 0.019(4) 0.000 0.000(4) 0.000 C4 0.043(5) 0.033(6) 0.037(5) 0.000 0.001(4) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C5A C5 0.990(5) . ? C5A C5 0.990(5) 3_655 ? C5A C4A 1.264(16) . ? C5A C6 1.461(12) . ? C5A C4 1.595(14) . ? C5A C4 1.595(14) 3_655 ? C5A C5A 1.737(17) 4_565 ? C5A C5A 1.737(17) 3_655 ? C4A C4 0.946(6) . ? C4A C4 0.946(6) 3_655 ? C4A N1 1.404(17) . ? C4A C5 1.616(15) . ? C4A C5 1.616(15) 3_655 ? C4A C4A 1.68(3) 4_565 ? C4A C4A 1.68(3) 3_655 ? C3 C3 0.50(5) 13_565 ? C3 C3A 0.95(3) . ? C3 C2 1.311(13) 13_565 ? C3 C3 1.33(2) 14 ? C3 C3 1.42(3) 2_565 ? C3 C3A 1.45(3) 13_565 ? C3 C2 1.508(17) . ? C3 C3A 1.604(17) 14 ? C3 C3A 1.94(2) 2_565 ? C3A C3A 1.26(2) 14 ? C3A C3 1.45(3) 13_565 ? C3A C2 1.456(12) 13_565 ? C3A C3 1.604(17) 14 ? C3A C3 1.94(2) 2_565 ? C2 C2 1.114(16) 13_565 ? C2 C3 1.311(13) 6_566 ? C2 C3 1.311(13) 13_565 ? C2 C3A 1.456(12) 6_566 ? C2 C3A 1.456(12) 13_565 ? C2 C3 1.508(17) 10_556 ? C2 C1 1.554(10) . ? C2 C1 1.863(10) 13_565 ? N1 C4A 1.404(17) 4_565 ? N1 C4A 1.404(17) 2_665 ? N1 C4A 1.404(17) 3_655 ? N1 C4 1.478(15) 4_565 ? N1 C4 1.478(15) . ? N1 C4 1.478(15) 3_655 ? N1 C4 1.478(15) 2_665 ? N1 Zn1 2.005(4) . ? Zn1 O1 1.991(3) 16 ? Zn1 O1 1.991(3) 3_655 ? Zn1 O1 1.991(3) . ? Zn1 O1 1.991(3) 14_655 ? Zn1 O1 1.991(3) 2_665 ? Zn1 O1 1.991(3) 15_665 ? Zn1 O1 1.991(3) 13_565 ? Zn1 O1 1.991(3) 4_565 ? Zn1 Zn1 2.9131(17) 9_666 ? O1 O1 0.877(8) 13_565 ? O1 C1 1.221(4) 13_565 ? O1 C1 1.524(6) . ? C1 C1 0.949(17) 13_565 ? C1 O1 1.221(4) 13_565 ? C1 O1 1.221(4) 6_566 ? C1 O1 1.524(6) 10_556 ? C1 C2 1.863(10) 13_565 ? C6 C6 1.409(10) 9_667 ? C6 C5A 1.461(12) 2_665 ? C6 C5A 1.461(12) 4_565 ? C6 C5A 1.461(12) 3_655 ? C6 C5 1.546(11) 4_565 ? C6 C5 1.546(11) . ? C6 C5 1.546(11) 2_665 ? C6 C5 1.546(11) 3_655 ? C5 C5A 0.990(5) 4_565 ? C5 C4 1.299(15) . ? C5 C4A 1.616(15) 4_565 ? C5 C5 1.898(15) 4_565 ? C5 C5 1.898(15) 3_655 ? C4 C4A 0.946(6) 4_565 ? C4 C5A 1.595(14) 4_565 ? C4 C4 1.81(2) 4_565 ? C4 C4 1.81(2) 3_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 C5A C5 147(2) . 3_655 ? C5 C5A C4A 90.8(10) . . ? C5 C5A C4A 90.8(10) 3_655 . ? C5 C5A C6 75.5(11) . . ? C5 C5A C6 75.5(11) 3_655 . ? C4A C5A C6 120.8(12) . . ? C5 C5A C4 54.4(9) . . ? C5 C5A C4 120.3(14) 3_655 . ? C4A C5A C4 36.4(4) . . ? C6 C5A C4 105.1(8) . . ? C5 C5A C4 120.3(14) . 3_655 ? C5 C5A C4 54.4(9) 3_655 3_655 ? C4A C5A C4 36.4(4) . 3_655 ? C6 C5A C4 105.1(8) . 3_655 ? C4 C5A C4 69.0(11) . 3_655 ? C5 C5A C5A 28.6(11) . 4_565 ? C5 C5A C5A 118.6(11) 3_655 4_565 ? C4A C5A C5A 88.6(7) . 4_565 ? C6 C5A C5A 53.5(2) . 4_565 ? C4 C5A C5A 57.0(5) . 4_565 ? C4 C5A C5A 104.8(7) 3_655 4_565 ? C5 C5A C5A 118.6(11) . 3_655 ? C5 C5A C5A 28.6(11) 3_655 3_655 ? C4A C5A C5A 88.6(7) . 3_655 ? C6 C5A C5A 53.5(2) . 3_655 ? C4 C5A C5A 104.8(7) . 3_655 ? C4 C5A C5A 57.0(5) 3_655 3_655 ? C5A C5A C5A 90.000(4) 4_565 3_655 ? C4 C4A C4 145(3) . 3_655 ? C4 C4A C5A 91.3(15) . . ? C4 C4A C5A 91.3(15) 3_655 . ? C4 C4A N1 75.1(17) . . ? C4 C4A N1 75.1(17) 3_655 . ? C5A C4A N1 124.5(15) . . ? C4 C4A C5 53.5(12) . . ? C4 C4A C5 121.8(19) 3_655 . ? C5A C4A C5 37.8(4) . . ? N1 C4A C5 107.7(10) . . ? C4 C4A C5 121.8(19) . 3_655 ? C4 C4A C5 53.5(12) 3_655 3_655 ? C5A C4A C5 37.8(4) . 3_655 ? N1 C4A C5 107.7(10) . 3_655 ? C5 C4A C5 71.9(9) . 3_655 ? C4 C4A C4A 27.7(17) . 4_565 ? C4 C4A C4A 117.7(17) 3_655 4_565 ? C5A C4A C4A 91.4(7) . 4_565 ? N1 C4A C4A 53.4(3) . 4_565 ? C5 C4A C4A 58.8(6) . 4_565 ? C5 C4A C4A 108.2(7) 3_655 4_565 ? C4 C4A C4A 117.7(17) . 3_655 ? C4 C4A C4A 27.7(17) 3_655 3_655 ? C5A C4A C4A 91.4(7) . 3_655 ? N1 C4A C4A 53.4(3) . 3_655 ? C5 C4A C4A 108.2(7) . 3_655 ? C5 C4A C4A 58.8(6) 3_655 3_655 ? C4A C4A C4A 90.000(5) 4_565 3_655 ? C3 C3 C3A 177.6(14) 13_565 . ? C3 C3 C2 103.5(11) 13_565 13_565 ? C3A C3 C2 78.5(16) . 13_565 ? C3 C3 C3 90.000(9) 13_565 14 ? C3A C3 C3 87.8(13) . 14 ? C2 C3 C3 122.6(6) 13_565 14 ? C3 C3 C3 69.4(19) 13_565 2_565 ? C3A C3 C3 108(2) . 2_565 ? C2 C3 C3 125.9(6) 13_565 2_565 ? C3 C3 C3 20.6(18) 14 2_565 ? C3 C3 C3A 1.6(9) 13_565 13_565 ? C3A C3 C3A 176(2) . 13_565 ? C2 C3 C3A 104.8(15) 13_565 13_565 ? C3 C3 C3A 88.5(8) 14 13_565 ? C3 C3 C3A 67.9(19) 2_565 13_565 ? C3 C3 C2 57.6(9) 13_565 . ? C3A C3 C2 124.3(18) . . ? C2 C3 C2 45.9(8) 13_565 . ? C3 C3 C2 117.9(6) 14 . ? C3 C3 C2 104.5(18) 2_565 . ? C3A C3 C2 59.0(11) 13_565 . ? C3 C3 C3A 126.2(8) 13_565 14 ? C3A C3 C3A 51.6(14) . 14 ? C2 C3 C3A 107.7(14) 13_565 14 ? C3 C3 C3A 36.2(8) 14 14 ? C3 C3 C3A 56.8(13) 2_565 14 ? C3A C3 C3A 124.7(12) 13_565 14 ? C2 C3 C3A 134.5(10) . 14 ? C3 C3 C3A 41.8(6) 13_565 2_565 ? C3A C3 C3A 136.0(14) . 2_565 ? C2 C3 C3A 122.7(13) 13_565 2_565 ? C3 C3 C3A 48.2(6) 14 2_565 ? C3 C3 C3A 27.6(14) 2_565 2_565 ? C3A C3 C3A 40.4(10) 13_565 2_565 ? C2 C3 C3A 85.3(12) . 2_565 ? C3A C3 C3A 84.4(8) 14 2_565 ? C3 C3A C3A 92.2(13) . 14 ? C3 C3A C3 0.8(5) . 13_565 ? C3A C3A C3 91.5(8) 14 13_565 ? C3 C3A C2 61.9(11) . 13_565 ? C3A C3A C2 120.7(6) 14 13_565 ? C3 C3A C2 62.6(7) 13_565 13_565 ? C3 C3A C3 56.0(16) . 14 ? C3A C3A C3 36.2(8) 14 14 ? C3 C3A C3 55.3(12) 13_565 14 ? C2 C3A C3 98.4(10) 13_565 14 ? C3 C3A C3 44.0(14) . 2_565 ? C3A C3A C3 48.2(6) 14 2_565 ? C3 C3A C3 43.3(11) 13_565 2_565 ? C2 C3A C3 90.4(9) 13_565 2_565 ? C3 C3A C3 12.0(12) 14 2_565 ? C2 C2 C3 76.5(11) 13_565 6_566 ? C2 C2 C3 76.5(11) 13_565 13_565 ? C3 C2 C3 108.0(14) 6_566 13_565 ? C2 C2 C3A 116.1(7) 13_565 6_566 ? C3 C2 C3A 39.6(11) 6_566 6_566 ? C3 C2 C3A 115.2(10) 13_565 6_566 ? C2 C2 C3A 116.1(7) 13_565 13_565 ? C3 C2 C3A 115.2(10) 6_566 13_565 ? C3 C2 C3A 39.6(11) 13_565 13_565 ? C3A C2 C3A 95.3(12) 6_566 13_565 ? C2 C2 C3 57.6(9) 13_565 . ? C3 C2 C3 101.0(10) 6_566 . ? C3 C2 C3 18.8(18) 13_565 . ? C3A C2 C3 121.0(9) 6_566 . ? C3A C2 C3 58.4(10) 13_565 . ? C2 C2 C3 57.6(9) 13_565 10_556 ? C3 C2 C3 18.8(18) 6_566 10_556 ? C3 C2 C3 101.0(10) 13_565 10_556 ? C3A C2 C3 58.4(10) 6_566 10_556 ? C3A C2 C3 121.0(9) 13_565 10_556 ? C3 C2 C3 89.3(13) . 10_556 ? C2 C2 C1 87.0(4) 13_565 . ? C3 C2 C1 121.7(7) 6_566 . ? C3 C2 C1 121.7(7) 13_565 . ? C3A C2 C1 122.2(7) 6_566 . ? C3A C2 C1 122.2(7) 13_565 . ? C3 C2 C1 116.1(7) . . ? C3 C2 C1 116.1(7) 10_556 . ? C2 C2 C1 56.4(3) 13_565 13_565 ? C3 C2 C1 108.6(9) 6_566 13_565 ? C3 C2 C1 108.6(9) 13_565 13_565 ? C3A C2 C1 132.0(6) 6_566 13_565 ? C3A C2 C1 132.0(6) 13_565 13_565 ? C3 C2 C1 95.4(8) . 13_565 ? C3 C2 C1 95.4(8) 10_556 13_565 ? C1 C2 C1 30.6(6) . 13_565 ? C4A N1 C4A 73.2(6) 4_565 . ? C4A N1 C4A 73.2(6) 4_565 2_665 ? C4A N1 C4A 115.0(14) . 2_665 ? C4A N1 C4A 115.0(14) 4_565 3_655 ? C4A N1 C4A 73.2(6) . 3_655 ? C4A N1 C4A 73.2(6) 2_665 3_655 ? C4A N1 C4 38.22(13) 4_565 4_565 ? C4A N1 C4 104.2(5) . 4_565 ? C4A N1 C4 38.22(14) 2_665 4_565 ? C4A N1 C4 104.2(5) 3_655 4_565 ? C4A N1 C4 38.22(13) 4_565 . ? C4A N1 C4 38.22(13) . . ? C4A N1 C4 104.2(5) 2_665 . ? C4A N1 C4 104.2(5) 3_655 . ? C4 N1 C4 75.3(5) 4_565 . ? C4A N1 C4 104.2(5) 4_565 3_655 ? C4A N1 C4 38.22(13) . 3_655 ? C4A N1 C4 104.2(5) 2_665 3_655 ? C4A N1 C4 38.22(13) 3_655 3_655 ? C4 N1 C4 119.6(11) 4_565 3_655 ? C4 N1 C4 75.3(5) . 3_655 ? C4A N1 C4 104.2(5) 4_565 2_665 ? C4A N1 C4 104.2(5) . 2_665 ? C4A N1 C4 38.22(14) 2_665 2_665 ? C4A N1 C4 38.22(14) 3_655 2_665 ? C4 N1 C4 75.3(5) 4_565 2_665 ? C4 N1 C4 119.6(11) . 2_665 ? C4 N1 C4 75.3(5) 3_655 2_665 ? C4A N1 Zn1 122.5(7) 4_565 . ? C4A N1 Zn1 122.5(7) . . ? C4A N1 Zn1 122.5(7) 2_665 . ? C4A N1 Zn1 122.5(7) 3_655 . ? C4 N1 Zn1 120.2(5) 4_565 . ? C4 N1 Zn1 120.2(5) . . ? C4 N1 Zn1 120.2(5) 3_655 . ? C4 N1 Zn1 120.2(5) 2_665 . ? O1 Zn1 O1 25.5(2) 16 3_655 ? O1 Zn1 O1 62.8(2) 16 . ? O1 Zn1 O1 88.02(2) 3_655 . ? O1 Zn1 O1 88.02(2) 16 14_655 ? O1 Zn1 O1 62.8(2) 3_655 14_655 ? O1 Zn1 O1 146.50(19) . 14_655 ? O1 Zn1 O1 112.8(2) 16 2_665 ? O1 Zn1 O1 88.02(2) 3_655 2_665 ? O1 Zn1 O1 158.58(13) . 2_665 ? O1 Zn1 O1 25.5(2) 14_655 2_665 ? O1 Zn1 O1 158.58(13) 16 15_665 ? O1 Zn1 O1 146.50(19) 3_655 15_665 ? O1 Zn1 O1 112.8(2) . 15_665 ? O1 Zn1 O1 88.02(2) 14_655 15_665 ? O1 Zn1 O1 62.8(2) 2_665 15_665 ? O1 Zn1 O1 88.02(2) 16 13_565 ? O1 Zn1 O1 112.8(2) 3_655 13_565 ? O1 Zn1 O1 25.5(2) . 13_565 ? O1 Zn1 O1 158.58(13) 14_655 13_565 ? O1 Zn1 O1 146.50(19) 2_665 13_565 ? O1 Zn1 O1 88.02(2) 15_665 13_565 ? O1 Zn1 O1 146.50(19) 16 4_565 ? O1 Zn1 O1 158.58(13) 3_655 4_565 ? O1 Zn1 O1 88.02(2) . 4_565 ? O1 Zn1 O1 112.8(2) 14_655 4_565 ? O1 Zn1 O1 88.02(2) 2_665 4_565 ? O1 Zn1 O1 25.5(2) 15_665 4_565 ? O1 Zn1 O1 62.8(2) 13_565 4_565 ? O1 Zn1 N1 100.71(7) 16 . ? O1 Zn1 N1 100.71(7) 3_655 . ? O1 Zn1 N1 100.71(7) . . ? O1 Zn1 N1 100.71(7) 14_655 . ? O1 Zn1 N1 100.71(7) 2_665 . ? O1 Zn1 N1 100.71(7) 15_665 . ? O1 Zn1 N1 100.71(7) 13_565 . ? O1 Zn1 N1 100.71(7) 4_565 . ? O1 Zn1 Zn1 79.29(7) 16 9_666 ? O1 Zn1 Zn1 79.29(7) 3_655 9_666 ? O1 Zn1 Zn1 79.29(7) . 9_666 ? O1 Zn1 Zn1 79.29(7) 14_655 9_666 ? O1 Zn1 Zn1 79.29(7) 2_665 9_666 ? O1 Zn1 Zn1 79.29(7) 15_665 9_666 ? O1 Zn1 Zn1 79.29(7) 13_565 9_666 ? O1 Zn1 Zn1 79.29(7) 4_565 9_666 ? N1 Zn1 Zn1 180.000(1) . 9_666 ? O1 O1 C1 91.7(4) 13_565 13_565 ? O1 O1 C1 53.2(3) 13_565 . ? C1 O1 C1 38.5(7) 13_565 . ? O1 O1 Zn1 77.27(11) 13_565 . ? C1 O1 Zn1 127.4(4) 13_565 . ? C1 O1 Zn1 110.5(4) . . ? C1 C1 O1 88.3(4) 13_565 13_565 ? C1 C1 O1 88.3(4) 13_565 6_566 ? O1 C1 O1 125.7(8) 13_565 6_566 ? C1 C1 O1 53.2(3) 13_565 10_556 ? O1 C1 O1 116.8(6) 13_565 10_556 ? O1 C1 O1 35.1(3) 6_566 10_556 ? C1 C1 O1 53.2(3) 13_565 . ? O1 C1 O1 35.1(3) 13_565 . ? O1 C1 O1 116.8(6) 6_566 . ? O1 C1 O1 90.9(5) 10_556 . ? C1 C1 C2 93.0(4) 13_565 . ? O1 C1 C2 117.2(4) 13_565 . ? O1 C1 C2 117.2(4) 6_566 . ? O1 C1 C2 113.3(5) 10_556 . ? O1 C1 C2 113.3(5) . . ? C1 C1 C2 56.4(3) 13_565 13_565 ? O1 C1 C2 111.3(4) 13_565 13_565 ? O1 C1 C2 111.3(4) 6_566 13_565 ? O1 C1 C2 88.4(4) 10_556 13_565 ? O1 C1 C2 88.4(4) . 13_565 ? C2 C1 C2 36.7(5) . 13_565 ? C6 C6 C5A 122.8(5) 9_667 2_665 ? C6 C6 C5A 122.8(5) 9_667 4_565 ? C5A C6 C5A 73.0(5) 2_665 4_565 ? C6 C6 C5A 122.8(5) 9_667 . ? C5A C6 C5A 114.4(10) 2_665 . ? C5A C6 C5A 73.0(5) 4_565 . ? C6 C6 C5A 122.8(5) 9_667 3_655 ? C5A C6 C5A 73.0(5) 2_665 3_655 ? C5A C6 C5A 114.4(10) 4_565 3_655 ? C5A C6 C5A 73.0(5) . 3_655 ? C6 C6 C5 119.8(4) 9_667 4_565 ? C5A C6 C5 38.29(12) 2_665 4_565 ? C5A C6 C5 38.29(12) 4_565 4_565 ? C5A C6 C5 104.3(5) . 4_565 ? C5A C6 C5 104.3(5) 3_655 4_565 ? C6 C6 C5 119.8(4) 9_667 . ? C5A C6 C5 104.3(5) 2_665 . ? C5A C6 C5 38.29(12) 4_565 . ? C5A C6 C5 38.29(12) . . ? C5A C6 C5 104.3(5) 3_655 . ? C5 C6 C5 75.7(4) 4_565 . ? C6 C6 C5 119.8(4) 9_667 2_665 ? C5A C6 C5 38.29(12) 2_665 2_665 ? C5A C6 C5 104.3(5) 4_565 2_665 ? C5A C6 C5 104.3(5) . 2_665 ? C5A C6 C5 38.29(12) 3_655 2_665 ? C5 C6 C5 75.7(4) 4_565 2_665 ? C5 C6 C5 120.4(8) . 2_665 ? C6 C6 C5 119.8(4) 9_667 3_655 ? C5A C6 C5 104.3(5) 2_665 3_655 ? C5A C6 C5 104.3(5) 4_565 3_655 ? C5A C6 C5 38.29(12) . 3_655 ? C5A C6 C5 38.29(12) 3_655 3_655 ? C5 C6 C5 120.4(8) 4_565 3_655 ? C5 C6 C5 75.7(4) . 3_655 ? C5 C6 C5 75.7(4) 2_665 3_655 ? C5A C5 C5A 123(2) 4_565 . ? C5A C5 C4 87.3(11) 4_565 . ? C5A C5 C4 87.3(11) . . ? C5A C5 C6 66.2(11) 4_565 . ? C5A C5 C6 66.2(11) . . ? C4 C5 C6 116.9(10) . . ? C5A C5 C4A 51.5(9) 4_565 4_565 ? C5A C5 C4A 106.7(14) . 4_565 ? C4 C5 C4A 35.8(5) . 4_565 ? C6 C5 C4A 97.2(7) . 4_565 ? C5A C5 C4A 106.7(14) 4_565 . ? C5A C5 C4A 51.5(9) . . ? C4 C5 C4A 35.8(5) . . ? C6 C5 C4A 97.2(7) . . ? C4A C5 C4A 62.5(12) 4_565 . ? C5A C5 C5 16.5(11) 4_565 4_565 ? C5A C5 C5 106.4(11) . 4_565 ? C4 C5 C5 88.0(6) . 4_565 ? C6 C5 C5 52.14(18) . 4_565 ? C4A C5 C5 54.0(5) 4_565 4_565 ? C4A C5 C5 98.4(7) . 4_565 ? C5A C5 C5 106.4(11) 4_565 3_655 ? C5A C5 C5 16.5(11) . 3_655 ? C4 C5 C5 88.0(6) . 3_655 ? C6 C5 C5 52.14(18) . 3_655 ? C4A C5 C5 98.4(7) 4_565 3_655 ? C4A C5 C5 54.0(5) . 3_655 ? C5 C5 C5 90.000(3) 4_565 3_655 ? C4A C4 C4A 125(3) 4_565 . ? C4A C4 C5 90.7(15) 4_565 . ? C4A C4 C5 90.7(15) . . ? C4A C4 N1 66.7(17) 4_565 . ? C4A C4 N1 66.7(17) . . ? C5 C4 N1 123.1(12) . . ? C4A C4 C5A 52.4(12) 4_565 4_565 ? C4A C4 C5A 110.7(19) . 4_565 ? C5 C4 C5A 38.3(4) . 4_565 ? N1 C4 C5A 100.4(9) . 4_565 ? C4A C4 C5A 110.7(19) 4_565 . ? C4A C4 C5A 52.4(12) . . ? C5 C4 C5A 38.3(4) . . ? N1 C4 C5A 100.4(9) . . ? C5A C4 C5A 66.0(9) 4_565 . ? C4A C4 C4 17.3(17) 4_565 4_565 ? C4A C4 C4 107.3(17) . 4_565 ? C5 C4 C4 92.0(6) . 4_565 ? N1 C4 C4 52.3(2) . 4_565 ? C5A C4 C4 55.5(5) 4_565 4_565 ? C5A C4 C4 101.8(6) . 4_565 ? C4A C4 C4 107.3(17) 4_565 3_655 ? C4A C4 C4 17.3(17) . 3_655 ? C5 C4 C4 92.0(6) . 3_655 ? N1 C4 C4 52.3(2) . 3_655 ? C5A C4 C4 101.8(6) 4_565 3_655 ? C5A C4 C4 55.5(5) . 3_655 ? C4 C4 C4 90.000(3) 4_565 3_655 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.239 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.031 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.028 -0.019 -0.005 1515 651 ' ' _platon_squeeze_details ; ; # Attachment '- 2,5-DM-BMOF.cif' data_2,5-DM-BMOF _database_code_depnum_ccdc_archive 'CCDC 834510' #TrackingRef '- 2,5-DM-BMOF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 N O6 Zn' _chemical_formula_sum 'C15 H12 N O6 Zn' _chemical_formula_weight 367.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 11.78(2) _cell_length_b 18.24(3) _cell_length_c 8.280(7) _cell_angle_alpha 90.00 _cell_angle_beta 123.97(10) _cell_angle_gamma 90.00 _cell_volume 1475(4) _cell_formula_units_Z 4 _cell_measurement_temperature 106.7 _cell_measurement_reflns_used 440 _cell_measurement_theta_min 2.9605 _cell_measurement_theta_max 29.0495 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.655 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 1.696 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.86738 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 106.7 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.4171 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5907 _diffrn_reflns_av_R_equivalents 0.1981 _diffrn_reflns_av_sigmaI/netI 0.2414 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1724 _reflns_number_gt 953 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlisPro, Oxford Diffraction Ltd.' _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^)+(0.0539P)^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 1724 _refine_ls_number_parameters 163 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.1803 _refine_ls_R_factor_gt 0.0906 _refine_ls_wR_factor_ref 0.1903 _refine_ls_wR_factor_gt 0.1535 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.018 _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 0.07934(14) 0.0000 0.71480(18) 0.0183(4) Uani 1 2 d S . . O1 O 0.1665(5) 0.0781(3) 0.6370(8) 0.0303(14) Uani 1 1 d . . . O2 O 0.0484(5) 0.0811(3) 0.3103(7) 0.0268(13) Uani 1 1 d . . . N1 N 0.2289(9) 0.0000 1.0022(12) 0.022(2) Uani 1 2 d S . . C1 C 0.1332(8) 0.1080(4) 0.4791(11) 0.0215(18) Uani 1 1 d . . . C2 C 0.1966(8) 0.1801(4) 0.4918(10) 0.0201(18) Uani 1 1 d . . . C11 C 0.4423(12) 0.0000 1.3942(14) 0.030(3) Uani 1 2 d S . . C13 C 0.3545(16) 0.0282(7) 1.058(2) 0.022(4) Uani 0.50 1 d PU . . H13 H 0.3657 0.0477 0.9610 0.026 Uiso 0.50 1 calc PR . . C12 C 0.4651(15) 0.0289(7) 1.2512(19) 0.018(4) Uani 0.50 1 d PU . . H12 H 0.5519 0.0475 1.2883 0.021 Uiso 0.50 1 calc PR . . C9 C 0.2124(14) 0.0177(8) 1.1424(19) 0.021(5) Uani 0.50 1 d PU . . H9 H 0.1238 0.0323 1.1065 0.025 Uiso 0.50 1 calc PR . . C10 C 0.3150(14) 0.0164(7) 1.3358(18) 0.018(4) Uani 0.50 1 d PU . . H10 H 0.2951 0.0274 1.4297 0.022 Uiso 0.50 1 calc PR . . C7 C 0.3354(17) 0.1981(8) 0.638(2) 0.025(4) Uani 0.50 1 d PU . 1 C6 C 0.1218(16) 0.2315(8) 0.357(2) 0.023(4) Uani 0.50 1 d PU . 1 H6 H 0.0328 0.2182 0.2510 0.028 Uiso 0.50 1 calc PR . 1 O3 O 0.4165(11) 0.1447(5) 0.7763(15) 0.031(3) Uani 0.50 1 d P A 1 C8 C 0.5561(16) 0.1640(8) 0.919(2) 0.034(5) Uani 0.50 1 d P A 1 H8C H 0.6030 0.1225 1.0069 0.051 Uiso 0.50 1 calc PR A 1 H8B H 0.5591 0.2065 0.9934 0.051 Uiso 0.50 1 calc PR A 1 H8A H 0.6018 0.1762 0.8531 0.051 Uiso 0.50 1 calc PR A 1 O4 O 0.1518(11) 0.2173(6) 0.7295(15) 0.032(3) Uani 0.50 1 d P . 2 C5 C 0.1385(19) 0.2756(9) 0.832(2) 0.037(5) Uani 0.50 1 d P . 2 H5C H 0.1015 0.2566 0.9040 0.056 Uiso 0.50 1 calc PR . 2 H5B H 0.0764 0.3128 0.7388 0.056 Uiso 0.50 1 calc PR . 2 H5A H 0.2285 0.2976 0.9230 0.056 Uiso 0.50 1 calc PR . 2 C4 C 0.2026(15) 0.2346(7) 0.615(2) 0.016(3) Uani 0.50 1 d PU . 2 C3 C 0.2385(15) 0.1981(8) 0.373(2) 0.020(3) Uani 0.50 1 d PU . 2 H3 H 0.2270 0.1634 0.2791 0.024 Uiso 0.50 1 calc PR . 2 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 0.0163(7) 0.0236(7) 0.0077(6) 0.000 0.0024(5) 0.000 O1 0.021(3) 0.027(3) 0.036(3) 0.010(3) 0.012(3) -0.003(2) O2 0.030(3) 0.028(3) 0.020(3) -0.005(2) 0.012(3) -0.004(2) N1 0.018(5) 0.032(5) 0.014(5) 0.000 0.007(4) 0.000 C1 0.022(4) 0.022(4) 0.023(4) 0.004(3) 0.014(4) 0.007(3) C2 0.018(4) 0.027(4) 0.008(4) -0.001(3) 0.004(3) -0.007(3) C11 0.017(7) 0.057(8) 0.008(6) 0.000 0.001(5) 0.000 C13 0.026(7) 0.021(7) 0.011(6) 0.003(5) 0.006(6) 0.002(5) C12 0.014(6) 0.029(7) 0.014(6) -0.005(5) 0.011(5) -0.004(5) C9 0.011(6) 0.033(10) 0.020(6) 0.001(5) 0.009(5) 0.001(5) C10 0.021(6) 0.021(10) 0.014(6) -0.005(5) 0.011(5) 0.004(5) C7 0.029(7) 0.021(7) 0.018(6) 0.014(6) 0.010(6) 0.002(6) C6 0.017(7) 0.033(7) 0.028(7) -0.004(6) 0.018(6) 0.000(6) O3 0.011(5) 0.036(6) 0.022(6) 0.005(5) -0.006(5) -0.006(5) C8 0.024(10) 0.026(9) 0.028(9) -0.008(7) 0.001(8) 0.004(7) O4 0.027(7) 0.038(7) 0.032(7) -0.001(5) 0.016(6) 0.002(5) C5 0.047(13) 0.046(11) 0.031(10) 0.000(9) 0.030(10) -0.005(9) C4 0.021(7) 0.021(6) 0.014(6) -0.001(5) 0.015(5) -0.002(5) C3 0.023(7) 0.014(6) 0.018(6) 0.001(5) 0.007(5) -0.006(5) _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 2.020(9) . ? Zn1 O2 2.036(6) 5_556 ? Zn1 O2 2.036(6) 2_556 ? Zn1 O1 2.058(6) . ? Zn1 O1 2.058(6) 6 ? Zn1 Zn1 2.952(5) 5_556 ? O1 C1 1.260(9) . ? O2 C1 1.277(9) . ? O2 Zn1 2.036(6) 5_556 ? N1 C9 1.320(15) . ? N1 C9 1.320(15) 6 ? N1 C13 1.381(17) . ? N1 C13 1.381(17) 6 ? C1 C2 1.487(10) . ? C2 C6 1.341(16) . ? C2 C3 1.366(17) . ? C2 C4 1.399(15) . ? C2 C7 1.425(17) . ? C11 C10 1.327(17) 6 ? C11 C10 1.327(17) . ? C11 C12 1.452(16) 6 ? C11 C12 1.452(16) . ? C11 C11 1.50(2) 5_658 ? C13 C12 1.390(19) . ? C13 H13 0.9500 . ? C12 H12 0.9500 . ? C9 C10 1.365(18) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C7 C6 1.37(2) 7_556 ? C7 O3 1.398(17) . ? C6 C7 1.37(2) 7_556 ? C6 H6 0.9500 . ? O3 C8 1.432(18) . ? C8 H8C 0.9800 . ? C8 H8B 0.9800 . ? C8 H8A 0.9800 . ? O4 C4 1.409(17) . ? O4 C5 1.421(19) . ? C5 H5C 0.9800 . ? C5 H5B 0.9800 . ? C5 H5A 0.9800 . ? C4 C3 1.387(19) 7_556 ? C3 C4 1.387(19) 7_556 ? C3 H3 0.9500 . ? 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 103.2(2) . 5_556 ? N1 Zn1 O2 103.2(2) . 2_556 ? O2 Zn1 O2 93.2(3) 5_556 2_556 ? N1 Zn1 O1 96.3(3) . . ? O2 Zn1 O1 160.1(2) 5_556 . ? O2 Zn1 O1 86.2(2) 2_556 . ? N1 Zn1 O1 96.3(3) . 6 ? O2 Zn1 O1 86.2(2) 5_556 6 ? O2 Zn1 O1 160.1(2) 2_556 6 ? O1 Zn1 O1 87.6(3) . 6 ? N1 Zn1 Zn1 165.3(3) . 5_556 ? O2 Zn1 Zn1 86.71(17) 5_556 5_556 ? O2 Zn1 Zn1 86.71(17) 2_556 5_556 ? O1 Zn1 Zn1 73.36(17) . 5_556 ? O1 Zn1 Zn1 73.36(17) 6 5_556 ? C1 O1 Zn1 134.7(5) . . ? C1 O2 Zn1 118.2(5) . 5_556 ? C9 N1 C13 105.8(10) . . ? C9 N1 C13 117.1(11) 6 . ? C9 N1 C13 117.1(11) . 6 ? C9 N1 C13 105.8(10) 6 6 ? C9 N1 Zn1 125.1(8) . . ? C9 N1 Zn1 125.1(8) 6 . ? C13 N1 Zn1 117.4(8) . . ? C13 N1 Zn1 117.4(8) 6 . ? O1 C1 O2 124.6(7) . . ? O1 C1 C2 117.2(7) . . ? O2 C1 C2 118.2(6) . . ? C3 C2 C4 117.8(10) . . ? C6 C2 C7 116.9(10) . . ? C6 C2 C1 119.2(9) . . ? C3 C2 C1 122.1(9) . . ? C4 C2 C1 119.9(8) . . ? C7 C2 C1 123.8(8) . . ? C10 C11 C12 107.9(11) 6 6 ? C10 C11 C12 118.1(11) . 6 ? C10 C11 C12 118.1(11) 6 . ? C10 C11 C12 107.9(11) . . ? C10 C11 C11 121.8(14) 6 5_658 ? C10 C11 C11 121.8(14) . 5_658 ? C12 C11 C11 119.4(13) 6 5_658 ? C12 C11 C11 119.4(13) . 5_658 ? N1 C13 C12 121.8(13) . . ? N1 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 C12 C11 117.1(13) . . ? C13 C12 H12 121.5 . . ? C11 C12 H12 121.5 . . ? N1 C9 C10 123.9(13) . . ? N1 C9 H9 118.0 . . ? C10 C9 H9 118.0 . . ? C11 C10 C9 120.7(13) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C6 C7 O3 123.8(14) 7_556 . ? C6 C7 C2 118.0(12) 7_556 . ? O3 C7 C2 118.0(12) . . ? C2 C6 C7 124.7(14) . 7_556 ? C2 C6 H6 117.7 . . ? C7 C6 H6 117.7 7_556 . ? C7 O3 C8 116.6(12) . . ? O3 C8 H8C 109.5 . . ? O3 C8 H8B 109.5 . . ? H8C C8 H8B 109.5 . . ? O3 C8 H8A 109.5 . . ? H8C C8 H8A 109.5 . . ? H8B C8 H8A 109.5 . . ? C4 O4 C5 117.5(12) . . ? O4 C5 H5C 109.5 . . ? O4 C5 H5B 109.5 . . ? H5C C5 H5B 109.5 . . ? O4 C5 H5A 109.5 . . ? H5C C5 H5A 109.5 . . ? H5B C5 H5A 109.5 . . ? C3 C4 C2 120.0(12) 7_556 . ? C3 C4 O4 122.3(13) 7_556 . ? C2 C4 O4 117.7(11) . . ? C2 C3 C4 122.0(13) . 7_556 ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 7_556 . ? 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 N1 Zn1 O1 C1 -179.9(7) . . . . ? O2 Zn1 O1 C1 12.1(12) 5_556 . . . ? O2 Zn1 O1 C1 -77.0(7) 2_556 . . . ? O1 Zn1 O1 C1 84.0(7) 6 . . . ? Zn1 Zn1 O1 C1 10.7(7) 5_556 . . . ? O2 Zn1 N1 C9 -65.7(8) 5_556 . . . ? O2 Zn1 N1 C9 30.8(8) 2_556 . . . ? O1 Zn1 N1 C9 118.5(8) . . . . ? O1 Zn1 N1 C9 -153.3(8) 6 . . . ? Zn1 Zn1 N1 C9 162.6(8) 5_556 . . . ? O2 Zn1 N1 C9 -30.8(8) 5_556 . . 6 ? O2 Zn1 N1 C9 65.7(8) 2_556 . . 6 ? O1 Zn1 N1 C9 153.3(8) . . . 6 ? O1 Zn1 N1 C9 -118.5(8) 6 . . 6 ? Zn1 Zn1 N1 C9 -162.6(8) 5_556 . . 6 ? O2 Zn1 N1 C13 156.5(7) 5_556 . . . ? O2 Zn1 N1 C13 -106.9(7) 2_556 . . . ? O1 Zn1 N1 C13 -19.3(7) . . . . ? O1 Zn1 N1 C13 68.9(7) 6 . . . ? Zn1 Zn1 N1 C13 24.8(7) 5_556 . . . ? O2 Zn1 N1 C13 106.9(7) 5_556 . . 6 ? O2 Zn1 N1 C13 -156.5(7) 2_556 . . 6 ? O1 Zn1 N1 C13 -68.9(7) . . . 6 ? O1 Zn1 N1 C13 19.3(7) 6 . . 6 ? Zn1 Zn1 N1 C13 -24.8(7) 5_556 . . 6 ? Zn1 O1 C1 O2 -21.1(12) . . . . ? Zn1 O1 C1 C2 158.3(5) . . . . ? Zn1 O2 C1 O1 17.0(10) 5_556 . . . ? Zn1 O2 C1 C2 -162.3(5) 5_556 . . . ? O1 C1 C2 C6 -143.1(10) . . . . ? O2 C1 C2 C6 36.3(12) . . . . ? O1 C1 C2 C3 140.4(10) . . . . ? O2 C1 C2 C3 -40.2(13) . . . . ? O1 C1 C2 C4 -45.9(12) . . . . ? O2 C1 C2 C4 133.5(10) . . . . ? O1 C1 C2 C7 38.5(13) . . . . ? O2 C1 C2 C7 -142.1(11) . . . . ? C9 N1 C13 C12 36.6(14) . . . . ? C9 N1 C13 C12 8.5(16) 6 . . . ? C13 N1 C13 C12 -76.2(12) 6 . . . ? Zn1 N1 C13 C12 -178.3(9) . . . . ? N1 C13 C12 C11 -1.3(17) . . . . ? C10 C11 C12 C13 -8.4(15) 6 . . . ? C10 C11 C12 C13 -34.5(13) . . . . ? C12 C11 C12 C13 77.9(11) 6 . . . ? C11 C11 C12 C13 -179.4(9) 5_658 . . . ? C9 N1 C9 C10 78.9(14) 6 . . . ? C13 N1 C9 C10 -39.2(16) . . . . ? C13 N1 C9 C10 6.5(18) 6 . . . ? Zn1 N1 C9 C10 179.2(10) . . . . ? C10 C11 C10 C9 -83.3(13) 6 . . . ? C12 C11 C10 C9 -10.7(17) 6 . . . ? C12 C11 C10 C9 34.5(15) . . . . ? C11 C11 C10 C9 178.4(10) 5_658 . . . ? N1 C9 C10 C11 3(2) . . . . ? C6 C2 C7 C6 7(2) . . . 7_556 ? C3 C2 C7 C6 62.2(15) . . . 7_556 ? C4 C2 C7 C6 -61.8(14) . . . 7_556 ? C1 C2 C7 C6 -174.8(11) . . . 7_556 ? C6 C2 C7 O3 -178.3(13) . . . . ? C3 C2 C7 O3 -122.9(15) . . . . ? C4 C2 C7 O3 113.1(15) . . . . ? C1 C2 C7 O3 0.1(19) . . . . ? C3 C2 C6 C7 -71.8(16) . . . 7_556 ? C4 C2 C6 C7 54.7(16) . . . 7_556 ? C7 C2 C6 C7 -7(2) . . . 7_556 ? C1 C2 C6 C7 174.2(13) . . . 7_556 ? C6 C7 O3 C8 -6(2) 7_556 . . . ? C2 C7 O3 C8 178.9(13) . . . . ? C6 C2 C4 C3 -61.0(14) . . . 7_556 ? C3 C2 C4 C3 -6(2) . . . 7_556 ? C7 C2 C4 C3 61.9(14) . . . 7_556 ? C1 C2 C4 C3 -179.9(10) . . . 7_556 ? C6 C2 C4 O4 121.3(14) . . . . ? C3 C2 C4 O4 176.3(12) . . . . ? C7 C2 C4 O4 -115.8(14) . . . . ? C1 C2 C4 O4 2.4(16) . . . . ? C5 O4 C4 C3 12(2) . . . 7_556 ? C5 O4 C4 C2 -170.6(12) . . . . ? C6 C2 C3 C4 70.1(14) . . . 7_556 ? C4 C2 C3 C4 6(2) . . . 7_556 ? C7 C2 C3 C4 -55.4(15) . . . 7_556 ? C1 C2 C3 C4 179.9(11) . . . 7_556 ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.302 _refine_diff_density_min -0.852 _refine_diff_density_rms 0.155