Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 222 _publ_contact_author_name 'Pascal D. C. Dietzel' _publ_contact_author_address ;SINTEF Chemistry and Materials Postboks 124, Blindern N-0314 Oslo Norway ; _publ_contact_author_email pascal.dietzel@sintef.no _publ_contact_author_phone +47-22067350 loop_ _publ_author_name _publ_author_address 'Dietzel, Pascal D. C.' ;SINTEF Chemistry and Materials Postboks 124, Blindern N-0314 Oslo Norway ; 'Blom, Richard' ;SINTEF Chemistry and Materials Postboks 124, Blindern N-0314 Oslo Norway ; 'Fjellvag, Helmer' ;Centre for Materials Science and Nanotechnology, Universitetet i Oslo Postboks 1033, Blindern N-0315 Oslo Norway ; _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Increased dimensionalities of zinc-diphenic acid metal-organic framework compounds by simultaneous or subsequent addition of neutral bridging ligands ; data_pd04ref _database_code_depnum_ccdc_archive 'CCDC 278006' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Aquozinc(II) biphenyl-2,2'-dicarboxylate ; _chemical_name_common ; Aquozinc(II) biphenyl-2,2'-dicarboxylate ; _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 O5 Zn' _chemical_formula_sum 'C14 H10 O5 Zn' _chemical_formula_weight 323.59 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' 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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.893(3) _cell_length_b 5.9756(15) _cell_length_c 17.382(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.086(5) _cell_angle_gamma 90.00 _cell_volume 1298.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6698 _cell_measurement_theta_min 2.416 _cell_measurement_theta_max 27.235 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.655 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 1.906 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5472 _exptl_absorpt_correction_T_max 0.7554 _exptl_absorpt_process_details 'Blessing, R. H. (1995) Acta Cryst. A51, 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX2 on goniometer platform' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16810 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 28.32 _reflns_number_total 3174 _reflns_number_gt 2633 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0424P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3174 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0680 _refine_ls_wR_factor_gt 0.0664 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.26454(13) 0.4298(3) 0.18540(9) 0.0308(3) Uani 1 1 d . . . C2 C 0.31681(13) 0.3877(3) 0.12449(9) 0.0303(3) Uani 1 1 d . . . C3 C 0.39761(15) 0.2270(3) 0.13767(11) 0.0429(4) Uani 1 1 d . . . C4 C 0.42551(17) 0.1075(4) 0.20784(12) 0.0502(5) Uani 1 1 d . . . C5 C 0.37273(16) 0.1461(3) 0.26700(12) 0.0472(5) Uani 1 1 d . . . C6 C 0.29311(15) 0.3047(3) 0.25574(10) 0.0388(4) Uani 1 1 d . . . C7 C 0.28994(15) 0.5047(2) 0.04592(10) 0.0311(3) Uani 1 1 d . . . C8 C 0.35888(16) 0.6732(3) 0.03287(12) 0.0452(4) Uani 1 1 d . . . C9 C 0.34189(19) 0.7831(4) -0.03910(13) 0.0541(5) Uani 1 1 d . . . C10 C 0.25742(19) 0.7221(4) -0.10105(12) 0.0531(5) Uani 1 1 d . . . C11 C 0.19026(18) 0.5514(3) -0.09032(12) 0.0443(4) Uani 1 1 d . . . C12 C 0.20467(14) 0.4418(3) -0.01717(9) 0.0308(3) Uani 1 1 d . . . C13 C 0.17589(13) 0.5973(3) 0.17576(9) 0.0327(4) Uani 1 1 d . . . C14 C 0.12454(13) 0.2632(3) -0.01109(9) 0.0315(3) Uani 1 1 d . . . O1 O 0.17743(10) 0.7653(2) 0.13140(7) 0.0407(3) Uani 1 1 d . . . O2 O 0.10413(11) 0.5644(2) 0.21236(8) 0.0438(3) Uani 1 1 d . . . O3 O 0.10525(10) 0.2270(2) 0.05527(7) 0.0421(3) Uani 1 1 d . . . O4 O 0.07965(10) 0.1645(2) -0.07432(7) 0.0462(3) Uani 1 1 d . . . O5 O 0.04352(11) 1.1370(2) 0.20611(7) 0.0408(3) Uani 1 1 d . . . Zn1 Zn 0.059034(15) 0.97516(3) 0.110444(10) 0.03056(8) Uani 1 1 d . . . H3 H 0.4322(15) 0.201(4) 0.0979(11) 0.050(6) Uiso 1 1 d . . . H4 H 0.482(2) 0.000(3) 0.2148(15) 0.065(8) Uiso 1 1 d . . . H5 H 0.3938(17) 0.066(4) 0.3149(14) 0.054(6) Uiso 1 1 d . . . H6 H 0.2528(14) 0.328(3) 0.2961(11) 0.041(5) Uiso 1 1 d . . . H8 H 0.4126(18) 0.715(4) 0.0777(14) 0.062(7) Uiso 1 1 d . . . H9 H 0.3860(19) 0.896(4) -0.0464(14) 0.069(7) Uiso 1 1 d . . . H10 H 0.2443(17) 0.797(4) -0.1497(13) 0.061(6) Uiso 1 1 d . . . H11 H 0.1425(19) 0.493(3) -0.1330(15) 0.047(6) Uiso 1 1 d . . . H13 H -0.0080(18) 1.126(4) 0.2279(13) 0.059(6) Uiso 1 1 d . . . H14 H 0.0669(19) 1.261(4) 0.2112(14) 0.060(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0299(9) 0.0303(8) 0.0310(8) -0.0023(6) 0.0055(7) -0.0033(7) C2 0.0274(9) 0.0301(8) 0.0320(8) -0.0034(6) 0.0042(7) -0.0020(7) C3 0.0369(10) 0.0451(10) 0.0463(10) -0.0046(8) 0.0094(8) 0.0064(8) C4 0.0436(12) 0.0420(10) 0.0594(12) 0.0042(9) 0.0017(9) 0.0121(9) C5 0.0478(12) 0.0419(11) 0.0446(10) 0.0104(9) -0.0032(9) -0.0020(9) C6 0.0417(10) 0.0404(9) 0.0325(9) 0.0000(7) 0.0052(8) -0.0067(8) C7 0.0332(9) 0.0305(8) 0.0317(8) -0.0039(6) 0.0117(7) -0.0004(6) C8 0.0430(11) 0.0473(11) 0.0451(10) -0.0039(8) 0.0107(9) -0.0150(9) C9 0.0619(14) 0.0463(11) 0.0596(13) 0.0038(9) 0.0256(11) -0.0190(10) C10 0.0712(15) 0.0499(12) 0.0392(10) 0.0113(9) 0.0150(10) -0.0107(10) C11 0.0532(12) 0.0435(10) 0.0333(9) 0.0050(8) 0.0047(9) -0.0063(9) C12 0.0345(9) 0.0272(8) 0.0310(8) 0.0003(6) 0.0084(7) -0.0012(7) C13 0.0361(10) 0.0314(8) 0.0313(8) -0.0076(7) 0.0094(7) -0.0035(7) C14 0.0298(9) 0.0298(8) 0.0331(8) 0.0011(6) 0.0045(7) 0.0020(6) O1 0.0419(7) 0.0340(6) 0.0498(7) 0.0048(5) 0.0182(6) 0.0048(5) O2 0.0486(8) 0.0392(7) 0.0519(8) -0.0049(6) 0.0283(6) 0.0003(6) O3 0.0521(8) 0.0393(7) 0.0349(6) 0.0017(5) 0.0108(6) -0.0153(6) O4 0.0453(8) 0.0534(8) 0.0380(7) -0.0100(6) 0.0069(6) -0.0174(6) O5 0.0480(8) 0.0373(8) 0.0436(7) -0.0102(5) 0.0235(6) -0.0114(6) Zn1 0.03495(14) 0.02816(11) 0.02870(12) -0.00067(7) 0.00798(9) -0.00323(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 C1 C6 1.404(2) . ? C1 C2 1.409(2) . ? C1 C13 1.498(2) . y C2 C3 1.394(2) . ? C2 C7 1.498(2) . ? C3 C4 1.383(3) . ? C3 H3 0.922(19) . ? C4 C5 1.384(3) . ? C4 H4 0.96(2) . ? C5 C6 1.376(3) . ? C5 H5 0.94(2) . ? C6 H6 0.979(18) . ? C7 C8 1.398(2) . ? C7 C12 1.402(3) . ? C8 C9 1.382(3) . ? C8 H8 0.94(2) . ? C9 C10 1.381(3) . ? C9 H9 0.91(2) . ? C10 C11 1.380(3) . ? C10 H10 0.94(2) . ? C11 C12 1.402(2) . ? C11 H11 0.91(2) . ? C12 C14 1.507(2) . y C13 O2 1.2593(19) . y C13 O1 1.269(2) . y C14 O3 1.2564(19) . y C14 O4 1.258(2) . y O1 Zn1 1.9402(12) . y O3 Zn1 1.9538(12) 1_545 y O4 Zn1 1.9342(13) 3_565 y O5 Zn1 1.9754(12) . y O5 H13 0.84(2) . ? O5 H14 0.80(2) . ? Zn1 O4 1.9342(13) 3_565 ? Zn1 O3 1.9538(12) 1_565 ? 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 C6 C1 C2 119.15(16) . . ? C6 C1 C13 119.00(14) . . ? C2 C1 C13 121.79(14) . . ? C3 C2 C1 118.32(15) . . ? C3 C2 C7 117.98(14) . . ? C1 C2 C7 123.70(15) . . ? C4 C3 C2 121.60(17) . . ? C4 C3 H3 120.3(13) . . ? C2 C3 H3 118.1(13) . . ? C3 C4 C5 119.99(18) . . ? C3 C4 H4 118.9(15) . . ? C5 C4 H4 121.1(15) . . ? C6 C5 C4 119.61(18) . . ? C6 C5 H5 121.4(13) . . ? C4 C5 H5 119.0(13) . . ? C5 C6 C1 121.30(16) . . ? C5 C6 H6 120.1(11) . . ? C1 C6 H6 118.5(11) . . ? C8 C7 C12 118.34(16) . . ? C8 C7 C2 117.97(17) . . ? C12 C7 C2 123.47(14) . . ? C9 C8 C7 121.5(2) . . ? C9 C8 H8 123.2(14) . . ? C7 C8 H8 115.1(13) . . ? C10 C9 C8 120.09(19) . . ? C10 C9 H9 119.2(16) . . ? C8 C9 H9 120.7(16) . . ? C11 C10 C9 119.43(18) . . ? C11 C10 H10 119.7(13) . . ? C9 C10 H10 120.9(13) . . ? C10 C11 C12 121.26(19) . . ? C10 C11 H11 119.7(14) . . ? C12 C11 H11 118.3(13) . . ? C11 C12 C7 119.34(16) . . ? C11 C12 C14 116.91(16) . . ? C7 C12 C14 123.74(14) . . ? O2 C13 O1 123.56(16) . . y O2 C13 C1 118.26(15) . . ? O1 C13 C1 118.18(14) . . ? O3 C14 O4 124.72(15) . . y O3 C14 C12 118.61(14) . . ? O4 C14 C12 116.65(14) . . ? C13 O1 Zn1 119.83(11) . . y C14 O3 Zn1 137.35(12) . 1_545 y C14 O4 Zn1 132.74(11) . 3_565 y Zn1 O5 H13 126.2(16) . . ? Zn1 O5 H14 115.8(16) . . ? H13 O5 H14 110(2) . . ? O4 Zn1 O1 113.89(6) 3_565 . y O4 Zn1 O3 122.76(6) 3_565 1_565 y O1 Zn1 O3 105.66(5) . 1_565 y O4 Zn1 O5 102.10(5) 3_565 . y O1 Zn1 O5 113.24(6) . . y O3 Zn1 O5 98.14(6) 1_565 . y _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.357 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.054 data_pd67ref _database_code_depnum_ccdc_archive 'CCDC 278007' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Triethylenediamminzin(II) 2,2'-biphenyldicarboxylate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H14 N O4 Zn' _chemical_formula_sum 'C17 H14 N O4 Zn' _chemical_formula_weight 361.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'C 2/m' _symmetry_space_group_name_Hall '-C 2y' 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 7.2726(17) _cell_length_b 22.632(5) _cell_length_c 9.378(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.421(3) _cell_angle_gamma 90.00 _cell_volume 1455.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 712 _cell_measurement_theta_min 2.923 _cell_measurement_theta_max 18.6225 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.002 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.650 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 1.707 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.565267 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details 'Blessing, R. H. (1995) Acta Cryst. A51, 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX II' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6187 _diffrn_reflns_av_R_equivalents 0.0871 _diffrn_reflns_av_sigmaI/netI 0.1313 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 28.30 _reflns_number_total 1766 _reflns_number_gt 970 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.0b (Crystal Impact, 2005)' _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^)+(0.0860P)^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 SHELXL _refine_ls_extinction_coef 0.034(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1766 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1114 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1568 _refine_ls_wR_factor_gt 0.1265 _refine_ls_goodness_of_fit_ref 0.942 _refine_ls_restrained_S_all 0.942 _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 0.33273(12) 0.0000 0.35454(9) 0.0304(4) Uani 1 2 d S . . O1 O 0.2261(5) 0.06356(15) 0.4611(4) 0.0422(10) Uani 1 1 d . . . O2 O 0.5201(6) -0.06207(18) 0.3255(4) 0.0521(11) Uani 1 1 d . . . N1 N 0.1289(8) 0.0000 0.1348(6) 0.0291(14) Uani 1 2 d S . . C1 C 0.3153(8) 0.0810(2) 0.5928(6) 0.0331(12) Uani 1 1 d . . . C2 C 0.2214(7) 0.1264(2) 0.6629(5) 0.0296(12) Uani 1 1 d . . . C3 C 0.0466(7) 0.1551(2) 0.5844(5) 0.0296(12) Uani 1 1 d . . . C4 C -0.0358(8) 0.1930(2) 0.6635(6) 0.0407(14) Uani 1 1 d . . . H4 H -0.1523 0.2119 0.6116 0.049 Uiso 1 1 calc R . . C5 C 0.0498(8) 0.2032(2) 0.8161(6) 0.0428(14) Uani 1 1 d . . . H5 H -0.0098 0.2280 0.8667 0.051 Uiso 1 1 calc R . . C6 C 0.2248(8) 0.1762(2) 0.8933(6) 0.0397(14) Uani 1 1 d . . . H6 H 0.2861 0.1835 0.9958 0.048 Uiso 1 1 calc R . . C7 C 0.3080(8) 0.1385(2) 0.8166(5) 0.0335(12) Uani 1 1 d . . . H7 H 0.4259 0.1204 0.8692 0.040 Uiso 1 1 calc R . . C8A C -0.074(2) 0.0000 0.1426(19) 0.062(6) Uani 0.50 2 d SP . . H8A1 H -0.0913 0.0347 0.1976 0.074 Uiso 0.25 1 calc PR . . H8A2 H -0.0913 -0.0347 0.1976 0.074 Uiso 0.25 1 calc PR . . C8B C 0.226(3) 0.0000 0.013(2) 0.076(7) Uani 0.50 2 d SP . . H8B1 H 0.3082 0.0347 0.0242 0.091 Uiso 0.25 1 calc PR . . H8B2 H 0.3082 -0.0347 0.0242 0.091 Uiso 0.25 1 calc PR . . C9A C 0.148(3) 0.0515(7) 0.0522(15) 0.075(5) Uani 0.50 1 d P . . H9A1 H 0.2750 0.0517 0.0400 0.090 Uiso 0.50 1 calc PR . . H9A2 H 0.1369 0.0866 0.1082 0.090 Uiso 0.50 1 calc PR . . C9B C 0.015(3) 0.0524(8) 0.1073(16) 0.104(8) Uani 0.50 1 d P . . H9B1 H 0.0992 0.0862 0.1137 0.125 Uiso 0.50 1 calc PR . . H9B2 H -0.0453 0.0567 0.1847 0.125 Uiso 0.50 1 calc PR . . 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 0.0304(6) 0.0382(6) 0.0196(5) 0.000 0.0044(4) 0.000 O1 0.043(2) 0.048(2) 0.031(2) -0.0097(17) 0.0053(18) 0.0083(19) O2 0.044(2) 0.073(3) 0.031(2) -0.004(2) 0.001(2) 0.022(2) N1 0.032(3) 0.029(3) 0.026(3) 0.000 0.008(3) 0.000 C1 0.036(3) 0.034(3) 0.030(3) -0.003(2) 0.012(3) -0.001(2) C2 0.035(3) 0.030(3) 0.025(3) -0.002(2) 0.011(2) 0.000(2) C3 0.032(3) 0.028(3) 0.027(3) -0.001(2) 0.007(2) -0.002(2) C4 0.039(3) 0.047(3) 0.032(3) 0.000(3) 0.007(3) 0.013(3) C5 0.051(4) 0.042(3) 0.035(3) -0.006(3) 0.015(3) 0.008(3) C6 0.047(4) 0.041(3) 0.027(3) -0.008(2) 0.007(3) -0.002(3) C7 0.032(3) 0.037(3) 0.026(3) 0.000(2) 0.002(2) -0.001(2) C8A 0.024(9) 0.13(2) 0.027(10) 0.000 -0.003(8) 0.000 C8B 0.048(12) 0.15(2) 0.034(11) 0.000 0.012(9) 0.000 C9A 0.085(12) 0.082(12) 0.031(8) 0.023(8) -0.019(8) -0.028(10) C9B 0.109(15) 0.102(13) 0.048(9) -0.046(9) -0.046(10) 0.082(13) _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 O2 2.037(4) 6 y Zn1 O2 2.037(4) . y Zn1 O1 2.046(3) . y Zn1 O1 2.046(3) 6 y Zn1 N1 2.101(5) . y Zn1 Zn1 2.9914(16) 5_656 ? O1 C1 1.253(6) . ? O2 C1 1.263(6) 5_656 ? N1 C9B 1.420(13) 6 ? N1 C9B 1.420(13) . ? N1 C9A 1.431(13) 6 ? N1 C9A 1.431(13) . ? N1 C8A 1.501(18) . ? N1 C8B 1.534(19) . ? C1 O2 1.263(6) 5_656 ? C1 C2 1.501(7) . ? C2 C7 1.394(6) . ? C2 C3 1.399(7) . ? C3 C4 1.392(7) . ? C3 C3 1.501(9) 2_556 ? C4 C5 1.377(7) . ? C4 H4 0.9300 . ? C5 C6 1.380(7) . ? C5 H5 0.9300 . ? C6 C7 1.379(7) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8A C8B 1.51(2) 5 ? C8A H8A1 0.9700 . ? C8A H8A2 0.9700 . ? C8B C8A 1.51(2) 5 ? C8B H8B1 0.9700 . ? C8B H8B2 0.9700 . ? C9A C9B 1.568(16) 2 ? C9A H9A1 0.9700 . ? C9A H9A2 0.9700 . ? C9B C9A 1.568(16) 2 ? C9B H9B1 0.9700 . ? C9B H9B2 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Zn1 O2 87.2(2) 6 . y O2 Zn1 O1 87.67(16) 6 . y O2 Zn1 O1 158.30(15) . . y O2 Zn1 O1 158.30(15) 6 6 y O2 Zn1 O1 87.67(16) . 6 y O1 Zn1 O1 89.4(2) . 6 y O2 Zn1 N1 98.86(15) 6 . y O2 Zn1 N1 98.86(15) . . y O1 Zn1 N1 102.76(15) . . y O1 Zn1 N1 102.76(15) 6 . y O2 Zn1 Zn1 75.20(11) 6 5_656 ? O2 Zn1 Zn1 75.20(11) . 5_656 ? O1 Zn1 Zn1 83.10(10) . 5_656 ? O1 Zn1 Zn1 83.10(10) 6 5_656 ? N1 Zn1 Zn1 171.63(17) . 5_656 ? C1 O1 Zn1 123.2(3) . . ? C1 O2 Zn1 134.0(3) 5_656 . ? C9B N1 C9B 113(2) 6 . ? C9B N1 C9A 51.4(10) 6 6 ? C9B N1 C9A 137.4(8) . 6 ? C9B N1 C9A 137.4(8) 6 . ? C9B N1 C9A 51.4(10) . . ? C9A N1 C9A 109.1(17) 6 . ? C9B N1 C8A 59.0(11) 6 . ? C9B N1 C8A 59.0(11) . . ? C9A N1 C8A 107.4(9) 6 . ? C9A N1 C8A 107.4(9) . . ? C9B N1 C8B 104.5(10) 6 . ? C9B N1 C8B 104.5(10) . . ? C9A N1 C8B 56.3(9) 6 . ? C9A N1 C8B 56.3(9) . . ? C8A N1 C8B 137.9(10) . . ? C9B N1 Zn1 110.9(6) 6 . ? C9B N1 Zn1 110.9(6) . . ? C9A N1 Zn1 111.6(6) 6 . ? C9A N1 Zn1 111.6(6) . . ? C8A N1 Zn1 109.7(7) . . ? C8B N1 Zn1 112.5(8) . . ? O1 C1 O2 124.5(5) . 5_656 ? O1 C1 C2 119.1(5) . . ? O2 C1 C2 116.4(4) 5_656 . ? C7 C2 C3 118.2(4) . . ? C7 C2 C1 118.2(4) . . ? C3 C2 C1 123.6(4) . . ? C4 C3 C2 118.8(4) . . ? C4 C3 C3 116.0(4) . 2_556 ? C2 C3 C3 124.6(5) . 2_556 ? C5 C4 C3 122.0(5) . . ? C5 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? C4 C5 C6 119.4(5) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C7 C6 C5 119.2(5) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 C2 122.3(5) . . ? C6 C7 H7 118.8 . . ? C2 C7 H7 118.8 . . ? N1 C8A C8B 111.8(13) . 5 ? N1 C8A H8A1 109.3 . . ? C8B C8A H8A1 109.3 5 . ? N1 C8A H8A2 109.3 . . ? C8B C8A H8A2 109.3 5 . ? H8A1 C8A H8A2 107.9 . . ? C8A C8B N1 110.3(14) 5 . ? C8A C8B H8B1 109.6 5 . ? N1 C8B H8B1 109.6 . . ? C8A C8B H8B2 109.6 5 . ? N1 C8B H8B2 109.6 . . ? H8B1 C8B H8B2 108.1 . . ? N1 C9A C9B 110.4(11) . 2 ? N1 C9A H9A1 109.6 . . ? C9B C9A H9A1 109.6 2 . ? N1 C9A H9A2 109.6 . . ? C9B C9A H9A2 109.6 2 . ? H9A1 C9A H9A2 108.1 . . ? N1 C9B C9A 111.9(11) . 2 ? N1 C9B H9B1 109.2 . . ? C9A C9B H9B1 109.2 2 . ? N1 C9B H9B2 109.2 . . ? C9A C9B H9B2 109.2 2 . ? H9B1 C9B H9B2 107.9 . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.914 _refine_diff_density_min -0.983 _refine_diff_density_rms 0.314 data_pd58ref _database_code_depnum_ccdc_archive 'CCDC 278008' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Biphenyl-2,2'-dicarboxylato-bis(4,4'-bipyridyl)-zinc(II) ; _chemical_name_common ; Biphenyl-2,2'-dicarboxylato-bis(4,4'-bipyridyl)-zinc(II) ; _chemical_melting_point ? _chemical_formula_moiety 'C24 H16 N2 O4 Zn' _chemical_formula_sum 'C24 H16 N2 O4 Zn' _chemical_formula_weight 461.76 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 'F d d d' _symmetry_space_group_name_Hall '-F 2uv 2vw' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 23.270(3) _cell_length_b 24.089(4) _cell_length_c 29.240(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 16391(4) _cell_formula_units_Z 32 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6348 _cell_measurement_theta_min 2.191 _cell_measurement_theta_max 26.801 _exptl_crystal_description 'square block' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 7552 _exptl_absorpt_coefficient_mu 1.233 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5313 _exptl_absorpt_correction_T_max 0.8367 _exptl_absorpt_process_details 'Blessing, R. H. (1995) Acta Cryst. A51, 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX2 on goniometer platform' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 32808 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 28.05 _reflns_number_total 4618 _reflns_number_gt 3806 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0463P)^2^+23.5419P] 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 4618 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0861 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 C1 C 0.24720(8) 0.59870(8) 0.05289(7) 0.0440(4) Uani 1 1 d . . . H1 H 0.2677 0.5842 0.0775 0.053 Uiso 1 1 calc R . . C2 C 0.18822(8) 0.60233(9) 0.05623(7) 0.0453(4) Uani 1 1 d . . . H2 H 0.1696 0.5908 0.0827 0.054 Uiso 1 1 calc R . . C3 C 0.15699(8) 0.62330(9) 0.01985(7) 0.0423(4) Uani 1 1 d . . . C4 C 0.18727(9) 0.64087(12) -0.01806(8) 0.0617(7) Uani 1 1 d . . . H4 H 0.1679 0.6559 -0.0430 0.074 Uiso 1 1 calc R . . C5 C 0.24633(9) 0.63610(11) -0.01901(8) 0.0554(6) Uani 1 1 d . . . H5 H 0.2661 0.6480 -0.0449 0.067 Uiso 1 1 calc R . . C6 C 0.41401(8) 0.49500(9) 0.01961(8) 0.0475(5) Uani 1 1 d . . . H6 H 0.4446 0.5162 0.0303 0.057 Uiso 1 1 calc R . . C7 C 0.41925(8) 0.43796(8) 0.01935(8) 0.0472(5) Uani 1 1 d . . . H7 H 0.4531 0.4212 0.0291 0.057 Uiso 1 1 calc R . . C8 C 0.37328(8) 0.40574(8) 0.00438(6) 0.0379(4) Uani 1 1 d . . . C9 C 0.32402(8) 0.43295(8) -0.01049(7) 0.0419(4) Uani 1 1 d . . . H9 H 0.2923 0.4129 -0.0206 0.050 Uiso 1 1 calc R . . C10 C 0.32286(8) 0.49000(8) -0.01008(7) 0.0422(4) Uani 1 1 d . . . H10 H 0.2901 0.5079 -0.0208 0.051 Uiso 1 1 calc R . . C11 C 0.44354(8) 0.68537(8) -0.09676(6) 0.0389(4) Uani 1 1 d . . . C12 C 0.40734(8) 0.71430(7) -0.12648(6) 0.0381(4) Uani 1 1 d . . . C13 C 0.43253(9) 0.74838(9) -0.15952(8) 0.0528(5) Uani 1 1 d . . . H13 H 0.4091 0.7671 -0.1802 0.063 Uiso 1 1 calc R . . C14 C 0.49149(10) 0.75504(9) -0.16220(9) 0.0602(6) Uani 1 1 d . . . H14 H 0.5071 0.7785 -0.1842 0.072 Uiso 1 1 calc R . . C15 C 0.52698(9) 0.72722(10) -0.13264(8) 0.0560(6) Uani 1 1 d . . . H15 H 0.5666 0.7320 -0.1341 0.067 Uiso 1 1 calc R . . C16 C 0.50325(9) 0.69207(10) -0.10074(8) 0.0502(5) Uani 1 1 d . . . H16 H 0.5274 0.6723 -0.0813 0.060 Uiso 1 1 calc R . . C17 C 0.45825(9) 0.68971(10) 0.10203(7) 0.0507(5) Uani 1 1 d . . . C18 C 0.46392(11) 0.74719(11) 0.10381(9) 0.0620(6) Uani 1 1 d . . . H18 H 0.4368 0.7692 0.0891 0.074 Uiso 1 1 calc R . . C19 C 0.50844(13) 0.77220(13) 0.12668(9) 0.0746(8) Uani 1 1 d . . . H19 H 0.5112 0.8107 0.1277 0.090 Uiso 1 1 calc R . . C20 C 0.54888(14) 0.73954(14) 0.14799(9) 0.0809(9) Uani 1 1 d . . . H20 H 0.5798 0.7559 0.1630 0.097 Uiso 1 1 calc R . . C21 C 0.54361(11) 0.68249(13) 0.14716(8) 0.0707(7) Uani 1 1 d . . . H21 H 0.5711 0.6610 0.1619 0.085 Uiso 1 1 calc R . . C22 C 0.49808(9) 0.65623(10) 0.12483(7) 0.0514(5) Uani 1 1 d . . . C23 C 0.42277(8) 0.64716(8) -0.05956(7) 0.0420(4) Uani 1 1 d . . . C24 C 0.41062(9) 0.66756(11) 0.07201(8) 0.0564(6) Uani 1 1 d . . . N1 N 0.27609(7) 0.61512(6) 0.01582(6) 0.0384(3) Uani 1 1 d . . . N2 N 0.36663(7) 0.52106(7) 0.00501(5) 0.0394(3) Uani 1 1 d . . . O1 O 0.36973(6) 0.64413(7) -0.05158(6) 0.0603(4) Uani 1 1 d . . . O2 O 0.45763(7) 0.62050(8) -0.03705(8) 0.0792(6) Uani 1 1 d . . . O3 O 0.41074(8) 0.61689(7) 0.06281(6) 0.0675(5) Uani 1 1 d . . . O4 O 0.37604(10) 0.69983(10) 0.05415(12) 0.1156(10) Uani 1 1 d . . . Zn1 Zn 0.364542(9) 0.606786(9) 0.008378(8) 0.03702(9) 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 C1 0.0368(10) 0.0484(11) 0.0468(11) 0.0106(9) -0.0037(8) 0.0013(8) C2 0.0378(10) 0.0524(11) 0.0457(11) 0.0083(9) 0.0027(8) -0.0051(8) C3 0.0305(9) 0.0490(11) 0.0475(11) -0.0001(8) -0.0003(8) -0.0023(8) C4 0.0328(10) 0.1000(19) 0.0522(13) 0.0261(13) -0.0032(9) 0.0042(11) C5 0.0336(10) 0.0841(16) 0.0486(12) 0.0210(11) 0.0018(9) 0.0019(10) C6 0.0353(10) 0.0441(11) 0.0632(13) -0.0032(9) -0.0112(9) 0.0019(8) C7 0.0344(9) 0.0432(11) 0.0640(13) 0.0005(9) -0.0110(9) 0.0071(8) C8 0.0365(9) 0.0385(10) 0.0388(10) -0.0004(7) 0.0012(7) 0.0040(8) C9 0.0346(9) 0.0436(10) 0.0475(11) -0.0047(8) -0.0049(8) 0.0008(8) C10 0.0350(9) 0.0440(11) 0.0477(11) -0.0014(8) -0.0071(8) 0.0069(8) C11 0.0339(9) 0.0405(10) 0.0422(10) -0.0080(8) 0.0033(7) -0.0054(7) C12 0.0376(9) 0.0300(8) 0.0466(10) -0.0053(7) 0.0063(8) -0.0042(7) C13 0.0514(12) 0.0394(11) 0.0676(14) 0.0094(10) 0.0115(10) 0.0001(9) C14 0.0592(14) 0.0427(12) 0.0788(16) 0.0010(11) 0.0275(12) -0.0142(10) C15 0.0378(10) 0.0607(13) 0.0695(15) -0.0160(11) 0.0130(10) -0.0169(10) C16 0.0356(10) 0.0621(13) 0.0528(12) -0.0083(10) 0.0008(9) -0.0059(9) C17 0.0419(10) 0.0654(14) 0.0449(11) -0.0159(10) 0.0068(9) -0.0038(10) C18 0.0594(14) 0.0683(15) 0.0583(14) -0.0129(12) 0.0047(11) -0.0036(12) C19 0.089(2) 0.0747(18) 0.0605(16) -0.0147(13) 0.0049(14) -0.0269(16) C20 0.083(2) 0.101(2) 0.0590(16) -0.0112(15) -0.0135(14) -0.0388(18) C21 0.0636(15) 0.098(2) 0.0510(14) -0.0012(13) -0.0156(11) -0.0149(14) C22 0.0460(11) 0.0707(14) 0.0374(11) -0.0095(10) 0.0030(8) -0.0069(10) C23 0.0371(9) 0.0444(10) 0.0446(11) -0.0032(8) 0.0001(8) 0.0011(8) C24 0.0387(11) 0.0716(15) 0.0591(14) -0.0157(12) 0.0006(10) 0.0031(11) N1 0.0306(7) 0.0408(9) 0.0438(9) 0.0040(7) -0.0019(6) 0.0017(6) N2 0.0355(8) 0.0395(8) 0.0431(9) 0.0000(6) -0.0035(6) 0.0037(7) O1 0.0351(7) 0.0837(12) 0.0623(10) 0.0302(9) 0.0056(7) 0.0018(7) O2 0.0456(9) 0.0931(14) 0.0988(15) 0.0435(11) -0.0014(9) 0.0100(9) O3 0.0760(11) 0.0646(11) 0.0618(11) -0.0164(8) -0.0309(9) 0.0074(9) O4 0.0738(13) 0.0893(15) 0.184(3) -0.0295(17) -0.0603(16) 0.0221(12) Zn1 0.03041(12) 0.04035(13) 0.04030(14) 0.00196(9) -0.00384(8) 0.00201(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.335(3) . ? C1 C2 1.379(3) . ? C1 H1 0.9300 . ? C2 C3 1.384(3) . ? C2 H2 0.9300 . ? C3 C4 1.380(3) . ? C3 C3 1.491(4) 14_455 ? C4 C5 1.379(3) . ? C4 H4 0.9300 . ? C5 N1 1.331(3) . ? C5 H5 0.9300 . ? C6 N2 1.339(2) . ? C6 C7 1.379(3) . ? C6 H6 0.9300 . ? C7 C8 1.392(3) . ? C7 H7 0.9300 . ? C8 C9 1.390(3) . ? C8 C8 1.483(4) 2 ? C9 C10 1.375(3) . ? C9 H9 0.9300 . ? C10 N2 1.338(2) . ? C10 H10 0.9300 . ? C11 C12 1.396(3) . ? C11 C16 1.404(3) . ? C11 C23 1.505(3) . y C12 C13 1.397(3) . ? C12 C12 1.508(4) 3_554 ? C13 C14 1.383(3) . ? C13 H13 0.9300 . ? C14 C15 1.370(4) . ? C14 H14 0.9300 . ? C15 C16 1.375(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.392(3) . ? C17 C22 1.398(3) . ? C17 C24 1.511(3) . y C18 C19 1.372(4) . ? C18 H18 0.9300 . ? C19 C20 1.376(4) . ? C19 H19 0.9300 . ? C20 C21 1.380(4) . ? C20 H20 0.9300 . ? C21 C22 1.396(3) . ? C21 H21 0.9300 . ? C22 C22 1.505(5) 8_554 ? C23 O2 1.226(3) . y C23 O1 1.258(2) . y C23 Zn1 2.594(2) . ? C24 O4 1.235(3) . y C24 O3 1.250(3) . y C24 Zn1 2.599(2) . ? N1 Zn1 2.0795(16) . y N2 Zn1 2.0679(17) . y O1 Zn1 1.9742(16) . y O3 Zn1 1.9359(16) . y 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 C1 C2 122.68(18) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 119.43(19) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 117.48(18) . . ? C4 C3 C3 119.53(14) . 14_455 ? C2 C3 C3 122.98(14) . 14_455 ? C5 C4 C3 119.9(2) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? N1 C5 C4 122.3(2) . . ? N1 C5 H5 118.8 . . ? C4 C5 H5 118.8 . . ? N2 C6 C7 122.57(19) . . ? N2 C6 H6 118.7 . . ? C7 C6 H6 118.7 . . ? C6 C7 C8 119.28(18) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? C9 C8 C7 117.97(18) . . ? C9 C8 C8 121.0(2) . 2 ? C7 C8 C8 121.0(2) . 2 ? C10 C9 C8 119.00(18) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? N2 C10 C9 123.15(17) . . ? N2 C10 H10 118.4 . . ? C9 C10 H10 118.4 . . ? C12 C11 C16 119.22(18) . . ? C12 C11 C23 124.16(16) . . ? C16 C11 C23 116.62(18) . . ? C11 C12 C13 118.07(18) . . ? C11 C12 C12 124.50(18) . 3_554 ? C13 C12 C12 117.31(18) . 3_554 ? C14 C13 C12 121.6(2) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C15 C14 C13 120.3(2) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 119.12(19) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C15 C16 C11 121.6(2) . . ? C15 C16 H16 119.2 . . ? C11 C16 H16 119.2 . . ? C18 C17 C22 119.6(2) . . ? C18 C17 C24 116.3(2) . . ? C22 C17 C24 124.0(2) . . ? C19 C18 C17 121.8(3) . . ? C19 C18 H18 119.1 . . ? C17 C18 H18 119.1 . . ? C18 C19 C20 119.1(3) . . ? C18 C19 H19 120.5 . . ? C20 C19 H19 120.5 . . ? C19 C20 C21 120.1(2) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C20 C21 C22 121.8(3) . . ? C20 C21 H21 119.1 . . ? C22 C21 H21 119.1 . . ? C21 C22 C17 117.7(2) . . ? C21 C22 C22 116.7(2) . 8_554 ? C17 C22 C22 125.46(17) . 8_554 ? O2 C23 O1 121.3(2) . . y O2 C23 C11 119.74(18) . . ? O1 C23 C11 118.97(18) . . ? O2 C23 Zn1 74.82(13) . . ? O1 C23 Zn1 47.46(10) . . ? C11 C23 Zn1 161.95(14) . . ? O4 C24 O3 121.7(2) . . y O4 C24 C17 120.1(2) . . ? O3 C24 C17 117.9(2) . . ? O4 C24 Zn1 77.46(16) . . ? O3 C24 Zn1 45.31(11) . . ? C17 C24 Zn1 156.54(15) . . ? C5 N1 C1 118.14(17) . . ? C5 N1 Zn1 118.13(13) . . ? C1 N1 Zn1 123.69(13) . . ? C10 N2 C6 118.01(17) . . ? C10 N2 Zn1 123.79(12) . . ? C6 N2 Zn1 118.19(13) . . ? C23 O1 Zn1 104.53(13) . . ? C24 O3 Zn1 107.37(15) . . ? O3 Zn1 O1 129.71(8) . . y O3 Zn1 N2 98.72(7) . . y O1 Zn1 N2 114.29(7) . . y O3 Zn1 N1 116.84(8) . . y O1 Zn1 N1 96.28(6) . . y N2 Zn1 N1 97.15(6) . . y O3 Zn1 C23 107.00(8) . . ? O1 Zn1 C23 28.01(6) . . ? N2 Zn1 C23 109.01(6) . . ? N1 Zn1 C23 124.13(6) . . ? O3 Zn1 C24 27.32(8) . . ? O1 Zn1 C24 110.72(8) . . ? N2 Zn1 C24 125.94(7) . . ? N1 Zn1 C24 106.21(7) . . ? C23 Zn1 C24 96.98(7) . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.628 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.053