# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email zhj@fjirsm.ac.cn _publ_contact_author_name 'Jian Zhang' loop_ _publ_author_name 'Jian Zhang' 'Fei Wang' 'Yan-Xi Tan' 'Yao Kang' data_1 _database_code_depnum_ccdc_archive 'CCDC 869698' #TrackingRef '- check.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H19 N5 O5 Zn' _chemical_formula_sum 'C16 H19 N5 O5 Zn' _chemical_formula_weight 426.74 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 P2(1)2(1)2 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' _cell_length_a 14.3885(5) _cell_length_b 15.4745(6) _cell_length_c 8.4241(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1875.67(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2365 _cell_measurement_theta_min 2.4128 _cell_measurement_theta_max 28.9375 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 1.347 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6920 _exptl_absorpt_correction_T_max 0.8260 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; SQUEEZE RESULTS (APPEND TO CIF) 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 1 -0.009 0.500 0.372 356.3 192.7 2 0.460 0.000 -0.372 356.3 183.5 _platon_squeeze_details It is notable that the amount of disordered solvent deduced from the thermogravimatic analysis result of 1 (one DMA per formula unit) is not consistent with what can be deduced from the SQUEEZE output (two DMA per formula unit). That is maybe due to the weak diffractions of these structurally disordered guest molecules in the porous structure. ; _diffrn_ambient_temperature 293(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, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2083 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4791 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0535 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3146 _reflns_number_gt 2649 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _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^)+(0.0641P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(2) _refine_ls_number_reflns 3146 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1162 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.24968(4) 1.18986(3) 0.21275(5) 0.02739(17) Uani 1 1 d . . . O1 O 0.0471(3) 1.2435(4) 0.1448(4) 0.081(2) Uani 1 1 d . . . O2 O 0.1428(2) 1.2134(3) 0.3435(4) 0.0502(12) Uani 1 1 d . . . O3 O 0.2226(2) 0.7659(2) -0.0385(4) 0.0440(9) Uani 1 1 d . . . O4 O 0.3279(3) 0.7475(2) 0.1527(4) 0.0463(9) Uani 1 1 d . . . C1 C -0.0575(3) 1.2690(4) 0.6803(6) 0.0362(13) Uani 1 1 d . . . C2 C 0.0126(3) 1.2542(3) 0.5657(5) 0.0291(13) Uani 1 1 d . . . H2A H 0.0734 1.2448 0.5986 0.035 Uiso 1 1 calc R . . C3 C -0.0078(3) 1.2535(4) 0.4081(5) 0.0386(15) Uani 1 1 d . . . C4 C -0.1002(3) 1.2666(4) 0.3614(6) 0.0451(14) Uani 1 1 d . . . H4A H -0.1163 1.2659 0.2545 0.054 Uiso 1 1 calc R . . C5 C -0.1669(3) 1.2805(4) 0.4761(5) 0.0447(14) Uani 1 1 d . . . H5A H -0.2284 1.2880 0.4449 0.054 Uiso 1 1 calc R . . C6 C 0.0662(3) 1.2351(4) 0.2897(6) 0.0381(14) Uani 1 1 d . . . C7 C 0.1959(4) 1.0241(3) 0.0551(5) 0.0380(12) Uani 1 1 d . . . C8 C 0.2019(3) 0.9360(3) 0.0299(5) 0.0357(11) Uani 1 1 d . . . H8A H 0.1613 0.9092 -0.0406 0.043 Uiso 1 1 calc R . . C9 C 0.2674(3) 0.8882(3) 0.1083(5) 0.0312(11) Uani 1 1 d . . . C10 C 0.3293(4) 0.9293(3) 0.2077(6) 0.0427(12) Uani 1 1 d . . . H10A H 0.3752 0.8984 0.2609 0.051 Uiso 1 1 calc R . . C11 C 0.3213(4) 1.0151(3) 0.2254(6) 0.0410(12) Uani 1 1 d . . . H11A H 0.3641 1.0428 0.2908 0.049 Uiso 1 1 calc R . . C12 C 0.2755(3) 0.7916(3) 0.0772(5) 0.0345(12) Uani 1 1 d . . . N1 N -0.1456(3) 1.2836(3) 0.6342(4) 0.0312(10) Uani 1 1 d . . . N2 N -0.0370(3) 1.2682(4) 0.8324(5) 0.0517(15) Uani 1 1 d . . . H2B H -0.0799 1.2770 0.9018 0.062 Uiso 1 1 calc R . . H2C H 0.0192 1.2589 0.8626 0.062 Uiso 1 1 calc R . . N3 N 0.2570(3) 1.0631(2) 0.1565(4) 0.0321(8) Uani 1 1 d . . . N4 N 0.1322(3) 1.0712(3) -0.0166(5) 0.0632(15) Uani 1 1 d . . . H4B H 0.1294 1.1259 0.0007 0.076 Uiso 1 1 calc R . . H4C H 0.0934 1.0473 -0.0806 0.076 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 0.0201(2) 0.0364(3) 0.0257(3) -0.00241(19) -0.0011(3) 0.0017(4) O1 0.066(3) 0.161(6) 0.0161(18) -0.022(3) 0.0096(18) 0.036(3) O2 0.026(2) 0.088(3) 0.0374(19) -0.015(2) 0.0065(16) 0.011(2) O3 0.030(2) 0.057(2) 0.0456(18) -0.0207(18) -0.0123(14) 0.0032(17) O4 0.040(2) 0.049(2) 0.0502(19) 0.0015(18) -0.0121(17) 0.0033(19) C1 0.023(3) 0.048(3) 0.037(3) -0.012(3) 0.007(2) -0.007(3) C2 0.017(2) 0.046(4) 0.024(2) -0.008(3) 0.0029(19) 0.005(2) C3 0.022(3) 0.055(4) 0.039(3) 0.006(3) -0.002(2) 0.000(3) C4 0.024(2) 0.082(4) 0.029(2) -0.005(3) 0.001(2) 0.004(3) C5 0.023(2) 0.084(4) 0.027(2) -0.013(3) -0.0003(19) 0.002(3) C6 0.025(3) 0.063(4) 0.026(3) -0.005(3) 0.000(2) 0.008(3) C7 0.045(3) 0.035(3) 0.033(3) -0.006(2) -0.007(2) -0.003(2) C8 0.028(2) 0.050(3) 0.029(2) 0.001(2) -0.008(2) -0.007(2) C9 0.025(3) 0.043(2) 0.026(2) -0.0027(19) -0.0011(19) 0.003(2) C10 0.038(3) 0.050(3) 0.041(3) -0.009(3) -0.017(2) 0.011(3) C11 0.040(3) 0.034(3) 0.049(3) -0.002(2) -0.015(3) 0.004(2) C12 0.026(3) 0.042(3) 0.035(2) 0.000(2) 0.008(2) -0.003(2) N1 0.020(2) 0.052(3) 0.0213(18) 0.0026(19) -0.0041(16) -0.003(2) N2 0.016(2) 0.103(4) 0.036(2) 0.007(3) -0.0107(17) 0.004(3) N3 0.0239(18) 0.0380(18) 0.0345(17) -0.0030(15) -0.007(2) -0.007(2) N4 0.059(3) 0.055(3) 0.076(4) -0.016(3) -0.046(3) 0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 1.923(3) 3 ? Zn1 O2 1.926(3) . ? Zn1 N1 2.025(4) 4_576 ? Zn1 N3 2.020(3) . ? O1 C6 1.258(7) . ? O2 C6 1.237(6) . ? O3 C12 1.299(5) . ? O3 Zn1 1.923(3) 3_545 ? O4 C12 1.200(5) . ? C1 N1 1.345(6) . ? C1 N2 1.315(7) . ? C1 C2 1.414(7) . ? C2 C3 1.360(6) . ? C2 H2A 0.9300 . ? C3 C4 1.401(7) . ? C3 C6 1.487(7) . ? C4 C5 1.379(7) . ? C4 H4A 0.9300 . ? C5 N1 1.368(5) . ? C5 H5A 0.9300 . ? C7 N3 1.367(6) . ? C7 N4 1.318(7) . ? C7 C8 1.382(7) . ? C8 C9 1.368(6) . ? C8 H8A 0.9300 . ? C9 C10 1.378(6) . ? C9 C12 1.521(6) . ? C10 C11 1.342(7) . ? C10 H10A 0.9300 . ? C11 N3 1.321(6) . ? C11 H11A 0.9300 . ? N1 Zn1 2.025(4) 4_476 ? N2 H2B 0.8600 . ? N2 H2C 0.8600 . ? N4 H4B 0.8600 . ? N4 H4C 0.8600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 O2 119.11(17) 3 . ? O3 Zn1 N1 101.97(15) 3 4_576 ? O2 Zn1 N1 101.07(13) . 4_576 ? O3 Zn1 N3 113.83(15) 3 . ? O2 Zn1 N3 111.06(19) . . ? N1 Zn1 N3 107.88(18) 4_576 . ? C6 O2 Zn1 123.6(3) . . ? C12 O3 Zn1 129.6(3) . 3_545 ? N1 C1 N2 119.6(5) . . ? N1 C1 C2 120.1(4) . . ? N2 C1 C2 120.3(5) . . ? C3 C2 C1 120.9(4) . . ? C3 C2 H2A 119.5 . . ? C1 C2 H2A 119.5 . . ? C2 C3 C4 118.6(4) . . ? C2 C3 C6 120.1(4) . . ? C4 C3 C6 121.3(4) . . ? C5 C4 C3 119.1(4) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? N1 C5 C4 122.1(4) . . ? N1 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? O2 C6 O1 125.3(5) . . ? O2 C6 C3 116.4(5) . . ? O1 C6 C3 118.3(5) . . ? N3 C7 N4 119.2(4) . . ? N3 C7 C8 119.5(5) . . ? N4 C7 C8 121.3(5) . . ? C7 C8 C9 120.2(5) . . ? C7 C8 H8A 119.9 . . ? C9 C8 H8A 119.9 . . ? C10 C9 C8 119.3(5) . . ? C10 C9 C12 120.6(4) . . ? C8 C9 C12 120.1(4) . . ? C11 C10 C9 118.0(5) . . ? C11 C10 H10A 121.0 . . ? C9 C10 H10A 121.0 . . ? N3 C11 C10 124.6(5) . . ? N3 C11 H11A 117.7 . . ? C10 C11 H11A 117.7 . . ? O4 C12 O3 126.2(5) . . ? O4 C12 C9 121.1(4) . . ? O3 C12 C9 112.7(4) . . ? C1 N1 C5 119.1(4) . . ? C1 N1 Zn1 123.5(3) . 4_476 ? C5 N1 Zn1 117.4(3) . 4_476 ? C1 N2 H2B 120.0 . . ? C1 N2 H2C 120.0 . . ? H2B N2 H2C 120.0 . . ? C11 N3 C7 118.5(4) . . ? C11 N3 Zn1 118.6(3) . . ? C7 N3 Zn1 122.9(3) . . ? C7 N4 H4B 120.0 . . ? C7 N4 H4C 120.0 . . ? H4B N4 H4C 120.0 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.344 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.085 #end data_2 _database_code_depnum_ccdc_archive 'CCDC 869699' #TrackingRef '- check.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety "C15 H17 N5 O5 Zn'" _chemical_formula_sum 'C15 H17 N5 O5 Zn' _chemical_formula_weight 412.71 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 Fddd 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 12.7589(13) _cell_length_b 22.66(3) _cell_length_c 24.053(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6953(8) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2108 _cell_measurement_theta_min 2.4648 _cell_measurement_theta_max 28.9201 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2752 _exptl_absorpt_coefficient_mu 1.451 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6737 _exptl_absorpt_correction_T_max 0.7630 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; SQUEEZE RESULTS (APPEND TO CIF) 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 1 0.072 0.125 0.125 305.0 13.1 2 -0.113 0.125 0.625 305.0 13.1 3 -0.088 0.375 0.375 305.0 13.4 4 0.089 0.375 0.875 305.0 13.4 5 0.072 0.625 0.625 305.0 13.1 6 -0.113 0.625 0.125 305.0 13.1 7 -0.088 0.875 0.875 305.0 13.4 8 0.089 0.875 0.375 305.0 13.4 _platon_squeeze_details It is notable that the amount of disordered solvent deduced from the thermogravimatic analysis result of 2 (one DMF per formula unit) is not consistent with what can be deduced from the SQUEEZE output (0.2 DMA per formula unit). That is maybe due to the weak diffractions of these structurally disordered guest molecules in the porous structure. ; _diffrn_ambient_temperature 293(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, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2083 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4228 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1537 _reflns_number_gt 1220 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _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^)+(0.0565P)^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 1537 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0923 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.8750 0.084002(19) 0.3750 0.02021(18) Uani 1 2 d S . . O1 O 0.57520(16) -0.08780(11) 0.55904(9) 0.0529(7) Uani 1 1 d . . . O2 O 0.72846(15) -0.12892(8) 0.57148(7) 0.0288(5) Uani 1 1 d . . . C1 C 0.6937(2) 0.01868(13) 0.43113(12) 0.0321(7) Uani 1 1 d . . . C2 C 0.6523(2) -0.01848(15) 0.47195(13) 0.0376(8) Uani 1 1 d . . . H2A H 0.5801 -0.0204 0.4770 0.045 Uiso 1 1 calc R . . C3 C 0.7165(2) -0.05194(13) 0.50431(11) 0.0291(7) Uani 1 1 d . . . C4 C 0.8248(2) -0.04805(15) 0.49628(12) 0.0352(7) Uani 1 1 d . . . H4A H 0.8710 -0.0704 0.5175 0.042 Uiso 1 1 calc R . . C5 C 0.8601(2) -0.01068(14) 0.45653(13) 0.0356(8) Uani 1 1 d . . . H5A H 0.9322 -0.0084 0.4510 0.043 Uiso 1 1 calc R . . C6 C 0.6698(2) -0.09209(14) 0.54770(11) 0.0310(7) Uani 1 1 d . . . N1 N 0.79814(16) 0.02351(10) 0.42438(9) 0.0263(5) Uani 1 1 d . . . N2 N 0.63090(18) 0.05041(15) 0.39808(13) 0.0581(10) Uani 1 1 d . . . H2C H 0.6574 0.0732 0.3732 0.070 Uiso 1 1 calc R . . H2D H 0.5640 0.0480 0.4017 0.070 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 0.0226(3) 0.0208(3) 0.0173(2) 0.000 -0.00112(15) 0.000 O1 0.0353(13) 0.0658(18) 0.0575(15) 0.0256(13) 0.0166(12) 0.0066(12) O2 0.0328(11) 0.0297(11) 0.0239(9) 0.0098(9) 0.0001(8) -0.0002(9) C1 0.0260(14) 0.0343(18) 0.0362(16) 0.0117(14) 0.0065(12) 0.0044(14) C2 0.0230(15) 0.046(2) 0.0439(18) 0.0175(16) 0.0063(13) 0.0048(14) C3 0.0279(14) 0.0308(17) 0.0286(15) 0.0075(13) 0.0044(11) 0.0011(14) C4 0.0300(15) 0.0407(19) 0.0348(16) 0.0164(15) -0.0034(12) 0.0062(15) C5 0.0238(15) 0.042(2) 0.0408(17) 0.0147(15) 0.0031(12) 0.0007(14) C6 0.0325(16) 0.0340(18) 0.0264(15) 0.0042(14) 0.0067(13) -0.0030(14) N1 0.0231(11) 0.0296(14) 0.0261(11) 0.0076(11) 0.0031(9) 0.0048(11) N2 0.0271(14) 0.081(2) 0.066(2) 0.0495(19) 0.0044(13) 0.0100(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 2.0261(18) 18_666 ? Zn1 O2 2.0261(18) 28_665 ? Zn1 N1 2.062(2) . ? Zn1 N1 2.062(2) 3_655 ? Zn1 O1 2.461(3) 18_666 ? Zn1 O1 2.461(3) 28_665 ? Zn1 C6 2.567(3) 18_666 ? Zn1 C6 2.567(3) 28_665 ? O1 C6 1.241(4) . ? O1 Zn1 2.461(3) 30_556 ? O2 C6 1.258(4) . ? O2 Zn1 2.0261(18) 30_556 ? C1 N2 1.338(4) . ? C1 N1 1.347(3) . ? C1 C2 1.397(4) . ? C2 C3 1.361(4) . ? C2 H2A 0.9300 . ? C3 C4 1.399(4) . ? C3 C6 1.507(4) . ? C4 C5 1.354(4) . ? C4 H4A 0.9300 . ? C5 N1 1.350(3) . ? C5 H5A 0.9300 . ? C6 Zn1 2.567(3) 30_556 ? N2 H2C 0.8600 . ? N2 H2D 0.8600 . ? 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 131.02(12) 18_666 28_665 ? O2 Zn1 N1 102.68(9) 18_666 . ? O2 Zn1 N1 109.37(9) 28_665 . ? O2 Zn1 N1 109.37(9) 18_666 3_655 ? O2 Zn1 N1 102.68(9) 28_665 3_655 ? N1 Zn1 N1 96.67(14) . 3_655 ? O2 Zn1 O1 57.34(7) 18_666 18_666 ? O2 Zn1 O1 86.73(8) 28_665 18_666 ? N1 Zn1 O1 89.10(11) . 18_666 ? N1 Zn1 O1 166.53(8) 3_655 18_666 ? O2 Zn1 O1 86.73(8) 18_666 28_665 ? O2 Zn1 O1 57.34(7) 28_665 28_665 ? N1 Zn1 O1 166.53(8) . 28_665 ? N1 Zn1 O1 89.10(11) 3_655 28_665 ? O1 Zn1 O1 87.94(14) 18_666 28_665 ? O2 Zn1 C6 28.86(8) 18_666 18_666 ? O2 Zn1 C6 109.57(10) 28_665 18_666 ? N1 Zn1 C6 97.02(11) . 18_666 ? N1 Zn1 C6 138.17(9) 3_655 18_666 ? O1 Zn1 C6 28.48(8) 18_666 18_666 ? O1 Zn1 C6 86.56(11) 28_665 18_666 ? O2 Zn1 C6 109.57(10) 18_666 28_665 ? O2 Zn1 C6 28.86(8) 28_665 28_665 ? N1 Zn1 C6 138.17(9) . 28_665 ? N1 Zn1 C6 97.02(11) 3_655 28_665 ? O1 Zn1 C6 86.56(11) 18_666 28_665 ? O1 Zn1 C6 28.48(8) 28_665 28_665 ? C6 Zn1 C6 98.56(15) 18_666 28_665 ? C6 O1 Zn1 80.46(17) . 30_556 ? C6 O2 Zn1 100.15(16) . 30_556 ? N2 C1 N1 118.5(3) . . ? N2 C1 C2 120.9(3) . . ? N1 C1 C2 120.5(3) . . ? C3 C2 C1 120.6(3) . . ? C3 C2 H2A 119.7 . . ? C1 C2 H2A 119.7 . . ? C2 C3 C4 118.7(3) . . ? C2 C3 C6 119.6(2) . . ? C4 C3 C6 121.6(3) . . ? C5 C4 C3 117.8(3) . . ? C5 C4 H4A 121.1 . . ? C3 C4 H4A 121.1 . . ? N1 C5 C4 124.6(3) . . ? N1 C5 H5A 117.7 . . ? C4 C5 H5A 117.7 . . ? O1 C6 O2 122.0(2) . . ? O1 C6 C3 119.3(3) . . ? O2 C6 C3 118.7(2) . . ? O1 C6 Zn1 71.05(15) . 30_556 ? O2 C6 Zn1 50.99(13) . 30_556 ? C3 C6 Zn1 169.6(2) . 30_556 ? C1 N1 C5 117.6(2) . . ? C1 N1 Zn1 126.45(18) . . ? C5 N1 Zn1 115.63(18) . . ? C1 N2 H2C 120.0 . . ? C1 N2 H2D 120.0 . . ? H2C N2 H2D 120.0 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.308 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.086 #end data_2a _database_code_depnum_ccdc_archive 'CCDC 869700' #TrackingRef '- check.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12.5 H12 N4 O4.5 Zn' _chemical_formula_sum 'C12.5 H12 N4 O4.5 Zn' _chemical_formula_weight 355.64 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 Fddd 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 12.7743(8) _cell_length_b 22.1735(15) _cell_length_c 24.5295(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6948.0(8) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3815 _cell_measurement_theta_min 2.0177 _cell_measurement_theta_max 27.4662 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2752 _exptl_absorpt_coefficient_mu 1.431 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6735 _exptl_absorpt_correction_T_max 0.7629 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; SQUEEZE RESULTS (APPEND TO CIF) 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 1 0.071 0.125 0.125 304.4 18.9 2 -0.112 0.125 0.625 304.4 18.9 3 -0.086 0.375 0.375 304.4 18.7 4 0.087 0.375 0.875 304.4 18.7 5 0.071 0.625 0.625 304.4 18.9 6 -0.112 0.625 0.125 304.4 18.9 7 -0.086 0.875 0.875 304.4 18.7 8 0.087 0.875 0.375 304.4 18.7 _platon_squeeze_details the CIF that the SQUEEZE process removed the contributions of some 150 electrons from the unit-cell contents. This then corresponds with 150/16 = 9 electrons per asymmetric (formula) unit. As a methanol CH~4~O molecule has 18 electrons. the contributions of 9/18 = 0.5 methanol molecule was removed by the SQUEEZE process ; _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 'Saturn724+ (2x2 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10449 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1530 _reflns_number_gt 1338 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0642P)^2^+3.3913P] 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 1530 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.1002 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _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 0.8750 0.084145(16) 0.3750 0.0217(2) Uani 1 2 d S . . O2 O 0.72911(15) -0.12877(7) 0.57177(7) 0.0290(4) Uani 1 1 d . . . O1 O 0.57625(17) -0.08481(9) 0.56102(8) 0.0497(6) Uani 1 1 d . . . C6 C 0.6702(2) -0.09030(11) 0.54915(10) 0.0307(6) Uani 1 1 d . . . C5 C 0.8609(2) -0.01054(13) 0.45684(11) 0.0359(7) Uani 1 1 d . . . H5A H 0.9328 -0.0080 0.4515 0.043 Uiso 1 1 calc R . . C1 C 0.69373(19) 0.01827(11) 0.43058(10) 0.0309(6) Uani 1 1 d . . . C2 C 0.6514(2) -0.01843(13) 0.47203(11) 0.0366(7) Uani 1 1 d . . . H2A H 0.5793 -0.0203 0.4770 0.044 Uiso 1 1 calc R . . C3 C 0.7167(2) -0.05127(11) 0.50490(10) 0.0303(6) Uani 1 1 d . . . C4 C 0.8248(2) -0.04760(12) 0.49693(10) 0.0361(6) Uani 1 1 d . . . H4A H 0.8708 -0.0698 0.5184 0.043 Uiso 1 1 calc R . . N1 N 0.79751(15) 0.02295(9) 0.42412(8) 0.0273(5) Uani 1 1 d . . . N2 N 0.63013(17) 0.04853(14) 0.39650(10) 0.0508(8) Uani 1 1 d . . . H2C H 0.6563 0.0705 0.3710 0.061 Uiso 1 1 calc R . . H2D H 0.5633 0.0459 0.4002 0.061 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 0.0237(3) 0.0235(3) 0.0178(3) 0.000 -0.00097(13) 0.000 O2 0.0308(11) 0.0336(10) 0.0227(9) 0.0083(7) 0.0019(8) -0.0005(7) O1 0.0318(12) 0.0627(15) 0.0544(13) 0.0253(10) 0.0163(11) 0.0074(9) C6 0.0310(16) 0.0343(15) 0.0268(13) 0.0054(11) 0.0051(12) -0.0010(11) C5 0.0250(14) 0.0441(17) 0.0387(15) 0.0145(12) 0.0024(11) 0.0028(11) C1 0.0266(14) 0.0340(14) 0.0323(13) 0.0075(11) 0.0042(11) 0.0042(10) C2 0.0249(14) 0.0466(17) 0.0381(15) 0.0149(12) 0.0068(12) 0.0042(12) C3 0.0299(15) 0.0322(14) 0.0288(13) 0.0068(10) 0.0047(11) 0.0022(11) C4 0.0288(16) 0.0447(16) 0.0349(14) 0.0146(12) 0.0007(12) 0.0045(12) N1 0.0240(12) 0.0320(11) 0.0259(10) 0.0073(9) 0.0020(8) 0.0024(8) N2 0.0263(14) 0.0708(19) 0.0553(16) 0.0395(15) 0.0061(11) 0.0087(11) _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 2.0371(17) 18_666 ? Zn1 O2 2.0371(17) 28_665 ? Zn1 N1 2.067(2) . ? Zn1 N1 2.0671(19) 3_655 ? Zn1 O1 2.4658(19) 18_666 ? Zn1 O1 2.4658(19) 28_665 ? Zn1 C6 2.569(2) 18_666 ? Zn1 C6 2.569(2) 28_665 ? O2 C6 1.266(3) . ? O2 Zn1 2.0371(17) 30_556 ? O1 C6 1.241(4) . ? O1 Zn1 2.4658(19) 30_556 ? C6 C3 1.510(3) . ? C6 Zn1 2.569(2) 30_556 ? C5 N1 1.360(3) . ? C5 C4 1.362(4) . ? C5 H5A 0.9300 . ? C1 N1 1.339(3) . ? C1 N2 1.345(3) . ? C1 C2 1.410(3) . ? C2 C3 1.369(4) . ? C2 H2A 0.9300 . ? C3 C4 1.398(4) . ? C4 H4A 0.9300 . ? N2 H2C 0.8600 . ? N2 H2D 0.8600 . ? 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 132.38(10) 18_666 28_665 ? O2 Zn1 N1 101.77(8) 18_666 . ? O2 Zn1 N1 109.02(7) 28_665 . ? O2 Zn1 N1 109.02(7) 18_666 3_655 ? O2 Zn1 N1 101.77(8) 28_665 3_655 ? N1 Zn1 N1 97.94(11) . 3_655 ? O2 Zn1 O1 57.50(7) 18_666 18_666 ? O2 Zn1 O1 87.07(7) 28_665 18_666 ? N1 Zn1 O1 89.23(8) . 18_666 ? N1 Zn1 O1 166.01(7) 3_655 18_666 ? O2 Zn1 O1 87.07(7) 18_666 28_665 ? O2 Zn1 O1 57.50(7) 28_665 28_665 ? N1 Zn1 O1 166.01(7) . 28_665 ? N1 Zn1 O1 89.23(8) 3_655 28_665 ? O1 Zn1 O1 86.42(11) 18_666 28_665 ? O2 Zn1 C6 29.07(8) 18_666 18_666 ? O2 Zn1 C6 110.34(8) 28_665 18_666 ? N1 Zn1 C6 96.52(8) . 18_666 ? N1 Zn1 C6 137.95(8) 3_655 18_666 ? O1 Zn1 C6 28.43(8) 18_666 18_666 ? O1 Zn1 C6 85.92(8) 28_665 18_666 ? O2 Zn1 C6 110.34(8) 18_666 28_665 ? O2 Zn1 C6 29.07(8) 28_665 28_665 ? N1 Zn1 C6 137.95(8) . 28_665 ? N1 Zn1 C6 96.52(8) 3_655 28_665 ? O1 Zn1 C6 85.92(8) 18_666 28_665 ? O1 Zn1 C6 28.43(8) 28_665 28_665 ? C6 Zn1 C6 98.61(11) 18_666 28_665 ? C6 O2 Zn1 99.48(16) . 30_556 ? C6 O1 Zn1 80.42(14) . 30_556 ? O1 C6 O2 122.6(2) . . ? O1 C6 C3 119.5(2) . . ? O2 C6 C3 117.8(2) . . ? O1 C6 Zn1 71.14(13) . 30_556 ? O2 C6 Zn1 51.45(12) . 30_556 ? C3 C6 Zn1 169.29(19) . 30_556 ? N1 C5 C4 123.7(3) . . ? N1 C5 H5A 118.2 . . ? C4 C5 H5A 118.2 . . ? N1 C1 N2 119.1(2) . . ? N1 C1 C2 120.6(2) . . ? N2 C1 C2 120.3(2) . . ? C3 C2 C1 119.9(3) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? C2 C3 C4 119.2(2) . . ? C2 C3 C6 119.2(2) . . ? C4 C3 C6 121.5(2) . . ? C5 C4 C3 118.0(2) . . ? C5 C4 H4A 121.0 . . ? C3 C4 H4A 121.0 . . ? C1 N1 C5 118.5(2) . . ? C1 N1 Zn1 126.44(16) . . ? C5 N1 Zn1 114.67(17) . . ? C1 N2 H2C 120.0 . . ? C1 N2 H2D 120.0 . . ? H2C N2 H2D 120.0 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.541 _refine_diff_density_min -0.513 _refine_diff_density_rms 0.081 #end