# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author_name 'Jian Zhang' _publ_contact_author_address ; State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, CAS Fuzhou, Fujian, China 350002 ; _publ_contact_author_email zhj@fjirsm.ac.cn _publ_contact_author_fax ? loop_ _publ_author_name 'Jian Zhang' 'Fei Wang' 'Yan-Xi Tan' 'Haixia Zhang' 'Hui Yang' 'Yao Kang' data_ZIF-A1 _database_code_depnum_ccdc_archive 'CCDC 805733' #TrackingRef 'ZIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 N7 O3 Zn' _chemical_formula_sum 'C14 H15 N7 O3 Zn' _chemical_formula_weight 394.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 18.2006(9) _cell_length_b 10.4443(7) _cell_length_c 9.0541(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1721.12(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2406 _cell_measurement_theta_min 2.5074 _cell_measurement_theta_max 28.2630 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 1.456 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7594 _exptl_absorpt_correction_T_max 0.7594 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 16.2083 _diffrn_reflns_number 4362 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0510 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.5074 _diffrn_reflns_theta_max 28.2630 _reflns_number_total 2803 _reflns_number_gt 2207 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) ; _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^)+(0.0360P)^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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.045(16) _refine_ls_number_reflns 2803 _refine_ls_number_parameters 226 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0707 _refine_ls_wR_factor_gt 0.0691 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _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 0.400306(16) -0.01884(3) -0.13211(8) 0.03023(11) Uani 1 1 d . . . C5 C 0.5012(3) 0.0241(4) -0.3733(7) 0.0355(11) Uani 1 1 d . . . H5A H 0.5298 -0.0384 -0.3278 0.043 Uiso 1 1 calc R . . N1 N 0.51899(15) 0.0740(3) -0.5050(4) 0.0352(8) Uani 1 1 d . . . N4 N 0.45776(17) 0.2366(3) -0.6532(5) 0.0453(9) Uani 1 1 d . . . C4 C 0.3990(2) 0.3106(4) -0.6469(8) 0.0532(12) Uani 1 1 d . . . H4B H 0.3921 0.3645 -0.7274 0.064 Uiso 1 1 calc R . . N2 N 0.43990(15) 0.0699(3) -0.3117(3) 0.0334(7) Uani 1 1 d . . . C3 C 0.3539(2) 0.2429(4) -0.4215(5) 0.0400(10) Uani 1 1 d . . . N3 N 0.34835(18) 0.3186(3) -0.5411(4) 0.0500(9) Uani 1 1 d . . . C2 C 0.41569(18) 0.1587(4) -0.4143(4) 0.0334(9) Uani 1 1 d . . . C1 C 0.46365(17) 0.1618(4) -0.5310(5) 0.0313(9) Uani 1 1 d . . . N5 N 0.30240(17) 0.2505(4) -0.3169(4) 0.0561(10) Uani 1 1 d . . . H5B H 0.2664 0.3032 -0.3266 0.067 Uiso 1 1 calc R . . H5C H 0.3052 0.2026 -0.2398 0.067 Uiso 1 1 calc R . . O2 O 0.33716(14) 0.1063(3) -0.0379(3) 0.0466(7) Uani 1 1 d . . . N6 N 0.16366(15) 0.3429(3) 0.2798(4) 0.0368(8) Uani 1 1 d . . . O1 O 0.31265(15) -0.0402(3) 0.1333(4) 0.0522(8) Uani 1 1 d . . . C6 C 0.3044(2) 0.0657(4) 0.0796(5) 0.0382(10) Uani 1 1 d . . . C11 C 0.2569(2) 0.2892(4) 0.1072(5) 0.0448(11) Uani 1 1 d . . . H11A H 0.2891 0.3155 0.0334 0.054 Uiso 1 1 calc R . . C7 C 0.2541(2) 0.1626(4) 0.1505(5) 0.0364(9) Uani 1 1 d . . . C10 C 0.2111(2) 0.3760(4) 0.1758(5) 0.0483(11) Uani 1 1 d . . . H10A H 0.2136 0.4615 0.1477 0.058 Uiso 1 1 calc R . . C9 C 0.1615(2) 0.2202(4) 0.3223(5) 0.0482(12) Uani 1 1 d . . . H9A H 0.1288 0.1964 0.3961 0.058 Uiso 1 1 calc R . . C8 C 0.2063(2) 0.1273(4) 0.2604(5) 0.0481(11) Uani 1 1 d . . . H8A H 0.2041 0.0429 0.2927 0.058 Uiso 1 1 calc R . . N7 N -0.0252(3) -0.1422(4) 0.3551(7) 0.0772(12) Uani 1 1 d . . . O3 O 0.0825(3) -0.0644(6) 0.4370(8) 0.134(2) Uani 1 1 d . . . C12 C 0.0320(5) -0.0778(8) 0.3341(13) 0.143(4) Uani 1 1 d . . . H12A H 0.0390 -0.0383 0.2431 0.171 Uiso 1 1 calc R . . C14 C -0.0423(6) -0.2074(9) 0.4841(11) 0.167(4) Uani 1 1 d . . . H14A H -0.0042 -0.1939 0.5556 0.250 Uiso 1 1 calc R . . H14B H -0.0466 -0.2972 0.4634 0.250 Uiso 1 1 calc R . . H14C H -0.0881 -0.1761 0.5226 0.250 Uiso 1 1 calc R . . C13 C -0.0772(6) -0.1483(8) 0.2398(11) 0.157(4) Uani 1 1 d . . . H13A H -0.0600 -0.0989 0.1573 0.236 Uiso 1 1 calc R . . H13B H -0.1232 -0.1142 0.2735 0.236 Uiso 1 1 calc R . . H13C H -0.0837 -0.2358 0.2101 0.236 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.02338(14) 0.0427(2) 0.02456(19) -0.0051(4) -0.0003(3) 0.00135(16) C5 0.0285(13) 0.053(3) 0.025(2) 0.004(2) 0.0017(14) 0.003(2) N1 0.0303(15) 0.0462(19) 0.029(2) 0.0052(16) 0.0028(15) 0.0013(14) N4 0.0447(16) 0.0475(18) 0.044(3) 0.009(2) -0.0010(19) 0.0045(14) C4 0.055(2) 0.056(2) 0.049(4) 0.015(3) -0.002(3) 0.004(2) N2 0.0287(15) 0.0433(18) 0.0283(19) 0.0017(16) 0.0019(14) 0.0037(14) C3 0.0342(18) 0.044(2) 0.041(3) -0.008(2) -0.003(2) 0.0063(17) N3 0.0459(18) 0.056(2) 0.048(2) 0.011(2) -0.0033(19) 0.0142(16) C2 0.0312(19) 0.040(2) 0.029(2) -0.0028(18) -0.0022(16) 0.0012(15) C1 0.0246(16) 0.037(2) 0.032(2) 0.0009(18) -0.0005(16) -0.0006(16) N5 0.0420(18) 0.078(3) 0.048(2) 0.011(2) 0.0052(19) 0.0291(19) O2 0.0467(15) 0.0511(18) 0.0418(19) -0.0036(14) 0.0189(15) 0.0139(14) N6 0.0289(14) 0.047(2) 0.035(2) -0.0029(16) 0.0084(15) 0.0042(14) O1 0.0420(15) 0.0473(18) 0.067(2) 0.0028(17) 0.0149(15) 0.0051(14) C6 0.0307(19) 0.046(2) 0.038(3) -0.009(2) 0.0045(19) -0.0002(18) C11 0.043(2) 0.052(3) 0.039(3) 0.000(2) 0.016(2) 0.001(2) C7 0.0296(18) 0.043(2) 0.036(3) -0.003(2) 0.0055(17) 0.0038(16) C10 0.046(2) 0.045(2) 0.053(3) 0.006(2) 0.015(2) 0.005(2) C9 0.048(2) 0.052(3) 0.045(3) 0.001(2) 0.0209(19) -0.0013(19) C8 0.050(2) 0.038(2) 0.056(3) 0.003(2) 0.015(2) 0.0026(19) N7 0.099(3) 0.076(3) 0.057(3) -0.009(3) 0.008(4) 0.007(2) O3 0.105(4) 0.132(4) 0.166(7) 0.000(4) 0.013(4) -0.009(4) C12 0.132(7) 0.113(6) 0.182(14) 0.002(7) 0.087(8) 0.004(6) C14 0.239(11) 0.173(9) 0.088(7) 0.058(7) 0.004(8) -0.031(8) C13 0.222(10) 0.114(7) 0.136(9) -0.049(7) -0.054(8) 0.042(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 1.938(3) . ? Zn1 N1 1.953(3) 2_655 ? Zn1 N2 2.006(3) . ? Zn1 N6 2.019(3) 4_544 ? C5 N1 1.341(7) . ? C5 N2 1.337(6) . ? C5 H5A 0.9300 . ? N1 C1 1.382(4) . ? N1 Zn1 1.953(3) 2_654 ? N4 C4 1.320(5) . ? N4 C1 1.359(5) . ? C4 N3 1.332(7) . ? C4 H4B 0.9300 . ? N2 C2 1.385(5) . ? C3 N3 1.345(5) . ? C3 N5 1.335(5) . ? C3 C2 1.429(5) . ? C2 C1 1.370(5) . ? N5 H5B 0.8600 . ? N5 H5C 0.8600 . ? O2 C6 1.292(5) . ? N6 C10 1.324(5) . ? N6 C9 1.338(5) . ? N6 Zn1 2.019(3) 4 ? O1 C6 1.218(5) . ? C6 C7 1.508(5) . ? C11 C10 1.380(6) . ? C11 C7 1.380(5) . ? C11 H11A 0.9300 . ? C7 C8 1.372(6) . ? C10 H10A 0.9300 . ? C9 C8 1.386(5) . ? C9 H9A 0.9300 . ? C8 H8A 0.9300 . ? N7 C12 1.254(8) . ? N7 C14 1.387(9) . ? N7 C13 1.411(9) . ? O3 C12 1.316(12) . ? C12 H12A 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? 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 N1 112.69(14) . 2_655 ? O2 Zn1 N2 104.96(12) . . ? N1 Zn1 N2 110.12(12) 2_655 . ? O2 Zn1 N6 108.32(11) . 4_544 ? N1 Zn1 N6 117.07(13) 2_655 4_544 ? N2 Zn1 N6 102.56(13) . 4_544 ? N1 C5 N2 115.6(5) . . ? N1 C5 H5A 122.2 . . ? N2 C5 H5A 122.2 . . ? C5 N1 C1 103.5(3) . . ? C5 N1 Zn1 126.2(3) . 2_654 ? C1 N1 Zn1 130.0(3) . 2_654 ? C4 N4 C1 111.4(4) . . ? N3 C4 N4 128.9(5) . . ? N3 C4 H4B 115.5 . . ? N4 C4 H4B 115.5 . . ? C5 N2 C2 103.0(4) . . ? C5 N2 Zn1 118.2(3) . . ? C2 N2 Zn1 137.7(2) . . ? N3 C3 N5 118.9(4) . . ? N3 C3 C2 117.2(4) . . ? N5 C3 C2 123.8(4) . . ? C4 N3 C3 119.3(4) . . ? C1 C2 N2 109.3(3) . . ? C1 C2 C3 116.9(4) . . ? N2 C2 C3 133.9(4) . . ? N4 C1 C2 126.2(3) . . ? N4 C1 N1 125.3(3) . . ? C2 C1 N1 108.5(3) . . ? C3 N5 H5B 120.0 . . ? C3 N5 H5C 120.0 . . ? H5B N5 H5C 120.0 . . ? C6 O2 Zn1 114.5(3) . . ? C10 N6 C9 118.3(3) . . ? C10 N6 Zn1 118.0(3) . 4 ? C9 N6 Zn1 123.7(3) . 4 ? O1 C6 O2 124.8(4) . . ? O1 C6 C7 121.0(4) . . ? O2 C6 C7 114.3(4) . . ? C10 C11 C7 118.6(4) . . ? C10 C11 H11A 120.7 . . ? C7 C11 H11A 120.7 . . ? C8 C7 C11 119.1(3) . . ? C8 C7 C6 120.9(4) . . ? C11 C7 C6 119.9(3) . . ? N6 C10 C11 122.9(4) . . ? N6 C10 H10A 118.6 . . ? C11 C10 H10A 118.6 . . ? N6 C9 C8 122.5(4) . . ? N6 C9 H9A 118.7 . . ? C8 C9 H9A 118.7 . . ? C7 C8 C9 118.5(4) . . ? C7 C8 H8A 120.7 . . ? C9 C8 H8A 120.7 . . ? C12 N7 C14 125.3(9) . . ? C12 N7 C13 117.9(9) . . ? C14 N7 C13 116.8(6) . . ? N7 C12 O3 121.9(10) . . ? N7 C12 H12A 119.0 . . ? O3 C12 H12A 119.0 . . ? N7 C14 H14A 109.5 . . ? N7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N7 C13 H13A 109.5 . . ? N7 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N7 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.899 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 99.76 _refine_diff_density_max 0.337 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.057 #end data_ZIF-A2 _database_code_depnum_ccdc_archive 'CCDC 805734' #TrackingRef 'ZIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H13 N7 O2 Zn2' _chemical_formula_weight 454.06 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 Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 12.0840(6) _cell_length_b 9.9231(4) _cell_length_c 14.3845(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1724.86(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2845 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 23.39 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max .23 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.749 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 2.807 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9927 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2875 _reflns_number_gt 2247 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0425P)^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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.015(19) _refine_ls_number_reflns 2875 _refine_ls_number_parameters 235 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0821 _refine_ls_wR_factor_gt 0.0744 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 Zn1 Zn 0.77641(5) 1.19023(6) 0.29077(4) 0.02951(18) Uani 1 1 d . . . Zn2 Zn 0.86971(5) 0.68583(6) 0.50946(4) 0.03001(17) Uani 1 1 d . . . O1 O 0.3799(4) 0.8044(4) 0.7544(3) 0.0516(14) Uani 1 1 d . . . O2 O 0.3942(4) 0.5846(5) 0.7743(4) 0.0765(17) Uani 1 1 d . . . N1 N 0.8168(5) 0.8094(5) 0.4107(3) 0.0359(13) Uani 1 1 d . . . N2 N 0.7783(4) 0.9995(5) 0.3373(3) 0.0305(12) Uani 1 1 d . . . N3 N 0.8798(4) 1.4989(5) 0.4657(3) 0.0335(13) Uani 1 1 d . . . N4 N 0.8428(4) 1.3121(4) 0.3847(3) 0.0323(12) Uani 1 1 d . . . N5 N 0.8586(4) 1.2113(4) 0.1707(3) 0.0353(13) Uani 1 1 d . . . N6 N 0.9909(4) 1.2508(4) 0.0670(3) 0.0349(12) Uani 1 1 d . . . N7 N 0.7399(4) 0.6950(5) 0.6015(3) 0.0357(13) Uani 1 1 d . . . C1 C 0.8448(5) 0.9367(6) 0.3948(4) 0.0361(15) Uani 1 1 d . . . H1A H 0.9061 0.9775 0.4219 0.043 Uiso 1 1 calc R . . C2 C 0.7011(5) 0.9074(5) 0.3123(4) 0.0446(17) Uani 1 1 d . . . H2A H 0.6417 0.9215 0.2723 0.054 Uiso 1 1 calc R . . C3 C 0.7268(6) 0.7899(6) 0.3567(4) 0.0425(17) Uani 1 1 d . . . H3B H 0.6884 0.7092 0.3507 0.051 Uiso 1 1 calc R . . C4 C 0.8075(6) 1.4325(6) 0.4103(4) 0.0362(14) Uani 1 1 d . . . H4A H 0.7398 1.4682 0.3920 0.043 Uiso 1 1 calc R . . C5 C 0.9661(6) 1.4137(6) 0.4725(4) 0.0471(17) Uani 1 1 d . . . H5A H 1.0306 1.4304 0.5058 0.057 Uiso 1 1 calc R . . C6 C 0.9450(6) 1.2992(6) 0.4233(5) 0.0426(17) Uani 1 1 d . . . H6B H 0.9920 1.2256 0.4171 0.051 Uiso 1 1 calc R . . C7 C 0.9640(5) 1.2448(6) 0.1552(4) 0.0328(13) Uani 1 1 d . . . H7A H 1.0140 1.2623 0.2029 0.039 Uiso 1 1 calc R . . C8 C 0.8972(6) 1.2168(7) 0.0218(4) 0.0498(18) Uani 1 1 d . . . H8A H 0.8897 1.2108 -0.0424 0.060 Uiso 1 1 calc R . . C9 C 0.8159(6) 1.1929(7) 0.0843(4) 0.0488(18) Uani 1 1 d . . . H9A H 0.7435 1.1681 0.0706 0.059 Uiso 1 1 calc R . . C10 C 0.6745(5) 0.8047(6) 0.6051(4) 0.0393(15) Uani 1 1 d . . . H10A H 0.6964 0.8808 0.5721 0.047 Uiso 1 1 calc R . . C11 C 0.5781(6) 0.8109(6) 0.6541(4) 0.0425(16) Uani 1 1 d . . . H11A H 0.5371 0.8902 0.6549 0.051 Uiso 1 1 calc R . . C12 C 0.5413(5) 0.6992(6) 0.7026(4) 0.0339(14) Uani 1 1 d . . . C13 C 0.6110(5) 0.5849(6) 0.7026(4) 0.0387(15) Uani 1 1 d . . . H13A H 0.5921 0.5091 0.7372 0.046 Uiso 1 1 calc R . . C14 C 0.7075(5) 0.5865(6) 0.6509(4) 0.0367(14) Uani 1 1 d . . . H14A H 0.7518 0.5098 0.6502 0.044 Uiso 1 1 calc R . . C15 C 0.4299(6) 0.6923(7) 0.7494(4) 0.0428(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0265(4) 0.0273(3) 0.0347(3) 0.0004(4) -0.0003(3) -0.0008(3) Zn2 0.0266(4) 0.0290(3) 0.0344(3) -0.0022(4) -0.0020(3) -0.0010(3) O1 0.027(3) 0.049(3) 0.078(4) -0.008(2) 0.011(2) 0.009(2) O2 0.049(3) 0.068(4) 0.112(4) 0.007(3) 0.037(3) -0.001(3) N1 0.038(4) 0.032(3) 0.038(3) 0.003(2) -0.008(3) -0.002(3) N2 0.026(3) 0.029(2) 0.037(3) -0.001(2) -0.004(2) -0.007(2) N3 0.038(4) 0.028(2) 0.035(2) -0.006(2) -0.006(2) -0.003(2) N4 0.030(3) 0.030(3) 0.037(3) -0.005(2) -0.001(2) 0.001(3) N5 0.037(4) 0.032(3) 0.037(3) 0.000(2) 0.000(2) -0.002(2) N6 0.040(3) 0.034(3) 0.032(3) 0.001(2) 0.002(3) -0.003(3) N7 0.029(3) 0.043(3) 0.036(3) -0.003(2) 0.007(2) 0.004(2) C1 0.034(4) 0.034(4) 0.041(4) 0.000(3) -0.005(3) -0.001(3) C2 0.049(4) 0.032(3) 0.053(4) 0.004(3) -0.016(3) -0.001(3) C3 0.045(5) 0.028(3) 0.055(4) 0.004(3) -0.010(4) -0.011(3) C4 0.035(4) 0.032(4) 0.041(3) -0.004(3) -0.005(3) 0.010(3) C5 0.042(4) 0.044(4) 0.055(4) -0.008(3) -0.016(3) 0.010(3) C6 0.036(4) 0.032(4) 0.060(4) -0.008(3) -0.016(3) 0.011(3) C7 0.024(4) 0.032(3) 0.042(3) 0.003(2) -0.007(3) -0.002(3) C8 0.036(4) 0.084(5) 0.029(4) 0.009(3) -0.007(3) -0.018(3) C9 0.030(4) 0.077(5) 0.039(4) -0.005(3) -0.006(3) -0.010(3) C10 0.035(4) 0.032(3) 0.051(4) -0.003(3) 0.008(3) 0.002(3) C11 0.036(4) 0.034(3) 0.057(4) -0.006(3) 0.006(3) 0.011(3) C12 0.026(4) 0.042(3) 0.034(3) -0.007(3) -0.001(3) -0.002(3) C13 0.041(4) 0.037(3) 0.038(3) 0.007(3) 0.002(3) 0.004(3) C14 0.035(4) 0.032(3) 0.043(3) 0.007(3) 0.003(3) 0.010(3) C15 0.038(4) 0.050(4) 0.041(3) -0.001(3) -0.004(3) -0.008(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 O1 1.961(4) 2_674 ? Zn1 N4 1.983(5) . ? Zn1 N5 2.004(5) . ? Zn1 N2 2.008(5) . ? Zn2 N3 1.963(5) 1_545 ? Zn2 N6 1.979(5) 2_775 ? Zn2 N1 1.982(5) . ? Zn2 N7 2.055(5) . ? O1 C15 1.268(7) . ? O1 Zn1 1.961(4) 2_675 ? O2 C15 1.206(7) . ? N1 C1 1.327(7) . ? N1 C3 1.351(8) . ? N2 C1 1.310(7) . ? N2 C2 1.355(7) . ? N3 C5 1.346(7) . ? N3 C4 1.354(7) . ? N3 Zn2 1.963(5) 1_565 ? N4 C4 1.321(7) . ? N4 C6 1.360(8) . ? N5 C7 1.334(8) . ? N5 C9 1.358(8) . ? N6 C7 1.311(7) . ? N6 C8 1.348(7) . ? N6 Zn2 1.979(5) 2_774 ? N7 C10 1.347(7) . ? N7 C14 1.348(7) . ? C1 H1A 0.9300 . ? C2 C3 1.365(8) . ? C2 H2A 0.9300 . ? C3 H3B 0.9300 . ? C4 H4A 0.9300 . ? C5 C6 1.362(8) . ? C5 H5A 0.9300 . ? C6 H6B 0.9300 . ? C7 H7A 0.9300 . ? C8 C9 1.353(9) . ? C8 H8A 0.9300 . ? C9 H9A 0.9300 . ? C10 C11 1.363(9) . ? C10 H10A 0.9300 . ? C11 C12 1.383(8) . ? C11 H11A 0.9300 . ? C12 C13 1.413(8) . ? C12 C15 1.507(9) . ? C13 C14 1.383(8) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 N4 123.7(2) 2_674 . ? O1 Zn1 N5 104.2(2) 2_674 . ? N4 Zn1 N5 108.8(2) . . ? O1 Zn1 N2 97.20(18) 2_674 . ? N4 Zn1 N2 110.06(19) . . ? N5 Zn1 N2 112.37(18) . . ? N3 Zn2 N6 112.4(2) 1_545 2_775 ? N3 Zn2 N1 112.00(19) 1_545 . ? N6 Zn2 N1 112.2(2) 2_775 . ? N3 Zn2 N7 107.2(2) 1_545 . ? N6 Zn2 N7 111.5(2) 2_775 . ? N1 Zn2 N7 100.9(2) . . ? C15 O1 Zn1 119.8(4) . 2_675 ? C1 N1 C3 104.0(5) . . ? C1 N1 Zn2 129.1(4) . . ? C3 N1 Zn2 125.7(4) . . ? C1 N2 C2 105.6(5) . . ? C1 N2 Zn1 131.8(4) . . ? C2 N2 Zn1 122.6(4) . . ? C5 N3 C4 103.7(5) . . ? C5 N3 Zn2 128.2(4) . 1_565 ? C4 N3 Zn2 127.5(4) . 1_565 ? C4 N4 C6 105.4(5) . . ? C4 N4 Zn1 127.6(4) . . ? C6 N4 Zn1 126.0(4) . . ? C7 N5 C9 104.1(5) . . ? C7 N5 Zn1 130.0(4) . . ? C9 N5 Zn1 125.9(4) . . ? C7 N6 C8 104.3(5) . . ? C7 N6 Zn2 129.1(4) . 2_774 ? C8 N6 Zn2 126.3(4) . 2_774 ? C10 N7 C14 117.1(5) . . ? C10 N7 Zn2 120.5(4) . . ? C14 N7 Zn2 121.7(4) . . ? N2 C1 N1 113.9(6) . . ? N2 C1 H1A 123.0 . . ? N1 C1 H1A 123.0 . . ? N2 C2 C3 107.1(6) . . ? N2 C2 H2A 126.4 . . ? C3 C2 H2A 126.4 . . ? N1 C3 C2 109.3(5) . . ? N1 C3 H3B 125.3 . . ? C2 C3 H3B 125.3 . . ? N4 C4 N3 113.3(6) . . ? N4 C4 H4A 123.3 . . ? N3 C4 H4A 123.3 . . ? N3 C5 C6 109.9(6) . . ? N3 C5 H5A 125.0 . . ? C6 C5 H5A 125.0 . . ? N4 C6 C5 107.7(6) . . ? N4 C6 H6B 126.2 . . ? C5 C6 H6B 126.2 . . ? N6 C7 N5 114.2(6) . . ? N6 C7 H7A 122.9 . . ? N5 C7 H7A 122.9 . . ? N6 C8 C9 109.5(5) . . ? N6 C8 H8A 125.3 . . ? C9 C8 H8A 125.3 . . ? C8 C9 N5 108.0(6) . . ? C8 C9 H9A 126.0 . . ? N5 C9 H9A 126.0 . . ? N7 C10 C11 123.9(6) . . ? N7 C10 H10A 118.1 . . ? C11 C10 H10A 118.1 . . ? C10 C11 C12 120.0(6) . . ? C10 C11 H11A 120.0 . . ? C12 C11 H11A 120.0 . . ? C11 C12 C13 116.8(6) . . ? C11 C12 C15 123.3(6) . . ? C13 C12 C15 119.7(6) . . ? C14 C13 C12 119.6(5) . . ? C14 C13 H13A 120.2 . . ? C12 C13 H13A 120.2 . . ? N7 C14 C13 122.5(5) . . ? N7 C14 H14A 118.8 . . ? C13 C14 H14A 118.8 . . ? O2 C15 O1 126.2(7) . . ? O2 C15 C12 119.5(6) . . ? O1 C15 C12 114.2(6) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.520 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.080 #end data_ZIF-A3 _database_code_depnum_ccdc_archive 'CCDC 805735' #TrackingRef 'ZIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 N4 O5 Zn2' _chemical_formula_weight 459.03 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/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 7.79870(10) _cell_length_b 30.8771(4) _cell_length_c 14.6120(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.7010(10) _cell_angle_gamma 90.00 _cell_volume 3403.40(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2165 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 21.93 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max .18 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.792 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 2.854 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16218 _diffrn_reflns_av_R_equivalents 0.0642 _diffrn_reflns_av_sigmaI/netI 0.0497 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3008 _reflns_number_gt 2216 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0340P)^2^+0.3445P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3008 _refine_ls_number_parameters 238 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0779 _refine_ls_wR_factor_gt 0.0701 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.013 _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 0.23113(6) 0.082103(14) 0.04434(3) 0.02914(14) Uani 1 1 d . . . Zn2 Zn 0.55057(6) 0.166291(14) 0.05830(3) 0.02891(14) Uani 1 1 d . . . O1 O 0.2497(4) 0.34142(8) -0.24666(19) 0.0442(8) Uani 1 1 d . . . O2 O 0.1355(4) 0.28801(8) -0.34521(18) 0.0383(7) Uani 1 1 d . . . O3 O 0.2788(4) -0.03955(9) 0.4560(2) 0.0470(8) Uani 1 1 d . . . O4 O 0.2723(5) -0.09326(9) 0.3552(2) 0.0656(10) Uani 1 1 d . . . O5 O 0.3995(4) 0.12623(9) 0.09795(18) 0.0362(7) Uani 1 1 d D . . H5A H 0.379(5) 0.1369(13) 0.146(2) 0.054 Uiso 1 1 d D . . N1 N 0.4266(4) 0.20902(10) -0.0472(2) 0.0315(8) Uani 1 1 d . . . N2 N 0.2375(4) 0.03910(10) 0.1537(2) 0.0335(8) Uani 1 1 d . . . N3 N -0.0076(4) 0.10889(10) 0.0012(2) 0.0329(8) Uani 1 1 d . . . N4 N -0.2609(4) 0.14107(10) 0.0077(2) 0.0327(8) Uani 1 1 d . . . C1 C 0.4602(5) 0.25140(13) -0.0347(3) 0.0428(11) Uani 1 1 d . . . H1A H 0.5305 0.2606 0.0233 0.051 Uiso 1 1 calc R . . C2 C 0.3969(6) 0.28198(13) -0.1027(3) 0.0418(11) Uani 1 1 d . . . H2A H 0.4244 0.3111 -0.0905 0.050 Uiso 1 1 calc R . . C3 C 0.2922(5) 0.26937(12) -0.1894(3) 0.0278(9) Uani 1 1 d . . . C4 C 0.2560(5) 0.22570(12) -0.2021(3) 0.0381(10) Uani 1 1 d . . . H4A H 0.1849 0.2158 -0.2593 0.046 Uiso 1 1 calc R . . C5 C 0.3242(5) 0.19694(13) -0.1310(3) 0.0390(10) Uani 1 1 d . . . H5B H 0.2981 0.1677 -0.1416 0.047 Uiso 1 1 calc R . . C6 C 0.2219(5) 0.30286(13) -0.2652(3) 0.0308(9) Uani 1 1 d . . . C7 C 0.2685(6) 0.05124(13) 0.2438(3) 0.0453(12) Uani 1 1 d . . . H7A H 0.2815 0.0806 0.2582 0.054 Uiso 1 1 calc R . . C8 C 0.2823(6) 0.02201(13) 0.3168(3) 0.0454(12) Uani 1 1 d . . . H8A H 0.3014 0.0317 0.3788 0.054 Uiso 1 1 calc R . . C9 C 0.2676(5) -0.02122(12) 0.2974(3) 0.0321(10) Uani 1 1 d . . . C10 C 0.2382(6) -0.03386(14) 0.2051(3) 0.0530(13) Uani 1 1 d . . . H10A H 0.2288 -0.0631 0.1895 0.064 Uiso 1 1 calc R . . C11 C 0.2227(6) -0.00308(13) 0.1357(3) 0.0502(12) Uani 1 1 d . . . H11A H 0.2009 -0.0122 0.0731 0.060 Uiso 1 1 calc R . . C12 C 0.2747(5) -0.05482(14) 0.3748(3) 0.0377(10) Uani 1 1 d . . . C13 C -0.1237(5) 0.11701(12) 0.0525(3) 0.0349(10) Uani 1 1 d . . . H13A H -0.1099 0.1068 0.1138 0.042 Uiso 1 1 calc R . . C14 C -0.2299(6) 0.14895(14) -0.0788(3) 0.0428(11) Uani 1 1 d . . . H14A H -0.3031 0.1649 -0.1273 0.051 Uiso 1 1 calc R . . C15 C -0.0752(5) 0.12978(14) -0.0823(3) 0.0413(11) Uani 1 1 d . . . H15A H -0.0239 0.1307 -0.1332 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0374(3) 0.0236(3) 0.0267(3) -0.0008(2) 0.0086(2) -0.0007(2) Zn2 0.0342(3) 0.0242(3) 0.0260(3) 0.0018(2) 0.00349(19) -0.0001(2) O1 0.074(2) 0.0195(17) 0.0325(18) 0.0016(13) 0.0014(15) -0.0008(14) O2 0.0544(18) 0.0295(16) 0.0241(16) -0.0018(12) -0.0028(13) 0.0018(14) O3 0.079(2) 0.0338(17) 0.0331(18) 0.0071(14) 0.0232(16) -0.0046(16) O4 0.123(3) 0.0224(18) 0.062(2) 0.0059(15) 0.043(2) 0.0031(18) O5 0.0473(17) 0.0337(17) 0.0293(17) -0.0082(13) 0.0131(14) -0.0128(14) N1 0.0359(19) 0.0253(19) 0.029(2) 0.0011(15) -0.0005(15) -0.0014(15) N2 0.044(2) 0.0249(19) 0.031(2) 0.0016(15) 0.0101(16) -0.0010(16) N3 0.0393(19) 0.029(2) 0.030(2) 0.0005(16) 0.0074(16) -0.0009(16) N4 0.0355(19) 0.031(2) 0.031(2) 0.0038(16) 0.0068(15) 0.0047(16) C1 0.056(3) 0.029(3) 0.032(3) -0.002(2) -0.009(2) -0.004(2) C2 0.062(3) 0.019(2) 0.034(3) 0.0028(19) -0.007(2) -0.003(2) C3 0.032(2) 0.025(2) 0.025(2) 0.0016(17) 0.0047(17) 0.0029(17) C4 0.053(3) 0.026(2) 0.028(2) -0.0019(19) -0.004(2) -0.004(2) C5 0.055(3) 0.020(2) 0.035(3) -0.0018(19) -0.001(2) -0.003(2) C6 0.038(2) 0.031(2) 0.025(2) 0.0049(19) 0.0105(18) 0.0040(19) C7 0.084(3) 0.020(2) 0.036(3) 0.000(2) 0.024(2) -0.004(2) C8 0.081(3) 0.027(3) 0.032(3) 0.000(2) 0.022(2) 0.000(2) C9 0.046(3) 0.022(2) 0.031(2) 0.0028(18) 0.014(2) 0.0001(19) C10 0.096(4) 0.022(2) 0.040(3) -0.002(2) 0.015(3) -0.010(2) C11 0.090(4) 0.030(3) 0.031(3) -0.005(2) 0.016(2) -0.014(3) C12 0.042(3) 0.033(3) 0.041(3) 0.007(2) 0.015(2) 0.000(2) C13 0.042(2) 0.034(3) 0.029(2) 0.0073(19) 0.009(2) 0.002(2) C14 0.049(3) 0.051(3) 0.026(3) 0.009(2) 0.005(2) 0.011(2) C15 0.048(3) 0.050(3) 0.029(3) 0.001(2) 0.015(2) 0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O5 1.916(3) . ? Zn1 O3 1.943(3) 6 ? Zn1 N3 1.988(3) . ? Zn1 N2 2.068(3) . ? Zn2 O5 1.897(3) . ? Zn2 N4 1.966(3) 1_655 ? Zn2 O2 1.986(3) 8_556 ? Zn2 N1 2.072(3) . ? O1 C6 1.228(5) . ? O2 C6 1.277(4) . ? O2 Zn2 1.986(3) 8_455 ? O3 C12 1.270(5) . ? O3 Zn1 1.943(3) 6_556 ? O4 C12 1.220(5) . ? O5 H5A 0.824(18) . ? N1 C1 1.338(5) . ? N1 C5 1.335(5) . ? N2 C11 1.328(5) . ? N2 C7 1.332(5) . ? N3 C13 1.337(4) . ? N3 C15 1.363(5) . ? N4 C13 1.330(4) . ? N4 C14 1.368(5) . ? N4 Zn2 1.966(3) 1_455 ? C1 C2 1.369(5) . ? C1 H1A 0.9300 . ? C2 C3 1.378(5) . ? C2 H2A 0.9300 . ? C3 C4 1.380(5) . ? C3 C6 1.513(5) . ? C4 C5 1.367(5) . ? C4 H4A 0.9300 . ? C5 H5B 0.9300 . ? C7 C8 1.380(5) . ? C7 H7A 0.9300 . ? C8 C9 1.363(5) . ? C8 H8A 0.9300 . ? C9 C10 1.366(5) . ? C9 C12 1.525(5) . ? C10 C11 1.374(6) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C13 H13A 0.9300 . ? C14 C15 1.357(5) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Zn1 O3 121.72(12) . 6 ? O5 Zn1 N3 108.85(12) . . ? O3 Zn1 N3 113.11(13) 6 . ? O5 Zn1 N2 105.15(12) . . ? O3 Zn1 N2 96.19(13) 6 . ? N3 Zn1 N2 110.41(13) . . ? O5 Zn2 N4 115.98(12) . 1_655 ? O5 Zn2 O2 111.56(11) . 8_556 ? N4 Zn2 O2 113.69(12) 1_655 8_556 ? O5 Zn2 N1 115.68(12) . . ? N4 Zn2 N1 103.01(13) 1_655 . ? O2 Zn2 N1 94.83(11) 8_556 . ? C6 O2 Zn2 113.5(2) . 8_455 ? C12 O3 Zn1 114.0(3) . 6_556 ? Zn2 O5 Zn1 138.84(14) . . ? Zn2 O5 H5A 105(3) . . ? Zn1 O5 H5A 112(3) . . ? C1 N1 C5 116.7(3) . . ? C1 N1 Zn2 118.9(3) . . ? C5 N1 Zn2 124.2(3) . . ? C11 N2 C7 117.2(4) . . ? C11 N2 Zn1 119.5(3) . . ? C7 N2 Zn1 123.1(3) . . ? C13 N3 C15 104.4(3) . . ? C13 N3 Zn1 127.9(3) . . ? C15 N3 Zn1 126.8(3) . . ? C13 N4 C14 104.2(3) . . ? C13 N4 Zn2 128.4(3) . 1_455 ? C14 N4 Zn2 127.0(3) . 1_455 ? N1 C1 C2 123.7(4) . . ? N1 C1 H1A 118.2 . . ? C2 C1 H1A 118.2 . . ? C1 C2 C3 119.5(4) . . ? C1 C2 H2A 120.2 . . ? C3 C2 H2A 120.2 . . ? C4 C3 C2 116.9(4) . . ? C4 C3 C6 123.1(4) . . ? C2 C3 C6 120.0(3) . . ? C5 C4 C3 120.4(4) . . ? C5 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? N1 C5 C4 122.8(4) . . ? N1 C5 H5B 118.6 . . ? C4 C5 H5B 118.6 . . ? O1 C6 O2 125.0(4) . . ? O1 C6 C3 119.3(4) . . ? O2 C6 C3 115.7(4) . . ? N2 C7 C8 122.6(4) . . ? N2 C7 H7A 118.7 . . ? C8 C7 H7A 118.7 . . ? C9 C8 C7 119.6(4) . . ? C9 C8 H8A 120.2 . . ? C7 C8 H8A 120.2 . . ? C10 C9 C8 118.0(4) . . ? C10 C9 C12 120.2(4) . . ? C8 C9 C12 121.8(4) . . ? C9 C10 C11 119.5(4) . . ? C9 C10 H10A 120.2 . . ? C11 C10 H10A 120.2 . . ? N2 C11 C10 123.1(4) . . ? N2 C11 H11A 118.5 . . ? C10 C11 H11A 118.5 . . ? O4 C12 O3 125.2(4) . . ? O4 C12 C9 119.4(4) . . ? O3 C12 C9 115.3(4) . . ? N4 C13 N3 113.9(4) . . ? N4 C13 H13A 123.1 . . ? N3 C13 H13A 123.1 . . ? C15 C14 N4 109.0(4) . . ? C15 C14 H14A 125.5 . . ? N4 C14 H14A 125.5 . . ? N3 C15 C14 108.5(4) . . ? N3 C15 H15A 125.7 . . ? C14 C15 H15A 125.7 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.311 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.081 #end