Electronic Supplementary Material for CrystEngComm Theis journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Ali Morsali' _publ_contact_author_address ; Department of Chemistry Tarbiat Modares University Tehran 14115-175 IRAN ; _publ_contact_author_email 'MORSALI A@YAHOO.COM' _publ_section_title ; Zinc(II) Nitrite Coordination Polymers Based on Rigid and Flexible Organic Nitrogen Donor Ligands ; loop_ _publ_author_name 'Ali Morsali' 'Maryam Amiri' 'Allen Hunter' 'Ghodrat Mahmoudi' 'Matthias Zeller' data_06mz303m _database_code_depnum_ccdc_archive 'CCDC 629971' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 N6 O4 Zn' _chemical_formula_weight 367.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/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 13.8208(14) _cell_length_b 6.8015(6) _cell_length_c 16.8268(16) _cell_angle_alpha 90.00 _cell_angle_beta 103.653(2) _cell_angle_gamma 90.00 _cell_volume 1537.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 571(2) _cell_measurement_reflns_used 3631 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 30.51 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.589 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744.0 _exptl_absorpt_coefficient_mu 1.627 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.521 _exptl_absorpt_correction_T_max 0.614 _exptl_absorpt_process_details 'SADABS in SAINT+ (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 571(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 AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 4401 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 28.28 _reflns_number_total 1903 _reflns_number_gt 1761 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART 5.630 (Bruker, 1997-2002)' _computing_cell_refinement 'SAINT+ 6.45 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0570P)^2^+0.4269P] 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 1903 _refine_ls_number_parameters 105 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0321 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0895 _refine_ls_wR_factor_gt 0.0879 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 0.5000 0.63920(4) 0.7500 0.04597(12) Uani 1 2 d S . . N2 N 0.38544(18) 0.8478(3) 0.82202(15) 0.0734(6) Uani 1 1 d . . . N1 N 0.56454(12) 0.4291(2) 0.83660(9) 0.0500(3) Uani 1 1 d . . . O2 O 0.35792(15) 0.7233(4) 0.76909(14) 0.0962(6) Uani 1 1 d . . . C3 C 0.64332(15) 0.1187(2) 0.93977(12) 0.0514(4) Uani 1 1 d . . . C4 C 0.67705(17) 0.1595(3) 0.87053(15) 0.0612(5) Uani 1 1 d . . . H4 H 0.7265 0.0824 0.8572 0.073 Uiso 1 1 calc R . . N3 N 0.73816(19) -0.1727(3) 0.97170(13) 0.0706(5) Uani 1 1 d . . . C2 C 0.56977(18) 0.2389(3) 0.95666(12) 0.0640(5) Uani 1 1 d . . . H2 H 0.5460 0.2176 1.0032 0.077 Uiso 1 1 calc R . . C1 C 0.53207(19) 0.3903(3) 0.90380(13) 0.0621(5) Uani 1 1 d . . . H1 H 0.4820 0.4687 0.9154 0.075 Uiso 1 1 calc R . . C6 C 0.67985(16) -0.0500(3) 0.99236(13) 0.0591(4) Uani 1 1 d . . . H6 H 0.6601 -0.0669 1.0411 0.071 Uiso 1 1 calc R . . C5 C 0.63700(16) 0.3143(3) 0.82162(14) 0.0622(5) Uani 1 1 d . . . H5 H 0.6613 0.3411 0.7757 0.075 Uiso 1 1 calc R . . O1 O 0.47585(19) 0.8552(3) 0.84147(18) 0.1034(8) 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 0.05215(18) 0.04308(18) 0.04550(18) 0.000 0.01717(12) 0.000 N2 0.0783(14) 0.0725(13) 0.0779(13) -0.0139(9) 0.0353(11) 0.0070(9) N1 0.0566(8) 0.0482(7) 0.0461(7) 0.0011(6) 0.0137(6) 0.0033(6) O2 0.0742(11) 0.1102(15) 0.1120(15) -0.0469(13) 0.0380(10) -0.0126(11) C3 0.0579(10) 0.0443(8) 0.0500(9) -0.0003(7) 0.0086(8) -0.0001(7) C4 0.0564(10) 0.0641(12) 0.0680(12) 0.0123(9) 0.0243(9) 0.0124(8) N3 0.0896(13) 0.0609(10) 0.0628(10) 0.0159(8) 0.0206(10) 0.0210(9) C2 0.0912(14) 0.0562(11) 0.0508(9) 0.0027(8) 0.0293(10) 0.0131(10) C1 0.0833(14) 0.0550(10) 0.0535(10) 0.0001(8) 0.0270(10) 0.0158(9) C6 0.0714(12) 0.0513(10) 0.0543(10) 0.0051(8) 0.0138(9) 0.0037(8) C5 0.0604(11) 0.0696(12) 0.0627(11) 0.0147(10) 0.0268(9) 0.0111(9) O1 0.0813(14) 0.1051(17) 0.124(2) -0.0422(12) 0.0244(13) -0.0031(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N1 2.0849(15) . ? Zn1 N1 2.0849(15) 2_656 ? Zn1 O2 2.1409(19) 2_656 ? Zn1 O2 2.1410(19) . ? Zn1 O1 2.209(2) 2_656 ? Zn1 O1 2.209(2) . ? N2 O1 1.216(3) . ? N2 O2 1.223(3) . ? N1 C1 1.338(3) . ? N1 C5 1.340(3) . ? C3 C4 1.381(3) . ? C3 C2 1.385(3) . ? C3 C6 1.464(3) . ? C4 C5 1.370(3) . ? C4 H4 0.9300 . ? N3 C6 1.265(3) . ? N3 N3 1.405(3) 7_647 ? C2 C1 1.380(3) . ? C2 H2 0.9300 . ? C1 H1 0.9300 . ? C6 H6 0.9300 . ? C5 H5 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 N1 Zn1 N1 93.49(9) . 2_656 ? N1 Zn1 O2 91.82(7) . 2_656 ? N1 Zn1 O2 109.54(9) 2_656 2_656 ? N1 Zn1 O2 109.54(9) . . ? N1 Zn1 O2 91.82(7) 2_656 . ? O2 Zn1 O2 149.01(13) 2_656 . ? N1 Zn1 O1 146.36(8) . 2_656 ? N1 Zn1 O1 94.53(9) 2_656 2_656 ? O2 Zn1 O1 54.77(8) 2_656 2_656 ? O2 Zn1 O1 102.80(10) . 2_656 ? N1 Zn1 O1 94.52(9) . . ? N1 Zn1 O1 146.36(8) 2_656 . ? O2 Zn1 O1 102.80(10) 2_656 . ? O2 Zn1 O1 54.77(8) . . ? O1 Zn1 O1 96.63(15) 2_656 . ? O1 N2 O2 110.4(2) . . ? C1 N1 C5 117.31(17) . . ? C1 N1 Zn1 123.54(13) . . ? C5 N1 Zn1 118.90(13) . . ? N2 O2 Zn1 98.96(16) . . ? C4 C3 C2 117.70(17) . . ? C4 C3 C6 122.03(18) . . ? C2 C3 C6 120.22(19) . . ? C5 C4 C3 119.47(19) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C6 N3 N3 111.7(3) . 7_647 ? C1 C2 C3 119.46(19) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? N1 C1 C2 122.76(19) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? N3 C6 C3 120.1(2) . . ? N3 C6 H6 119.9 . . ? C3 C6 H6 119.9 . . ? N1 C5 C4 123.3(2) . . ? N1 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? N2 O1 Zn1 95.72(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Zn1 N1 C1 -107.37(18) 2_656 . . . ? O2 Zn1 N1 C1 142.92(19) 2_656 . . . ? O2 Zn1 N1 C1 -14.20(19) . . . . ? O1 Zn1 N1 C1 149.08(19) 2_656 . . . ? O1 Zn1 N1 C1 39.92(18) . . . . ? N1 Zn1 N1 C5 66.76(15) 2_656 . . . ? O2 Zn1 N1 C5 -42.95(18) 2_656 . . . ? O2 Zn1 N1 C5 159.93(16) . . . . ? O1 Zn1 N1 C5 -36.8(2) 2_656 . . . ? O1 Zn1 N1 C5 -145.94(18) . . . . ? O1 N2 O2 Zn1 -4.2(3) . . . . ? N1 Zn1 O2 N2 84.15(19) . . . . ? N1 Zn1 O2 N2 178.50(19) 2_656 . . . ? O2 Zn1 O2 N2 -46.86(17) 2_656 . . . ? O1 Zn1 O2 N2 -86.4(2) 2_656 . . . ? O1 Zn1 O2 N2 2.67(18) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C6 C3 C4 C5 177.1(2) . . . . ? C4 C3 C2 C1 1.2(3) . . . . ? C6 C3 C2 C1 -176.2(2) . . . . ? C5 N1 C1 C2 -0.3(3) . . . . ? Zn1 N1 C1 C2 173.96(18) . . . . ? C3 C2 C1 N1 -1.0(4) . . . . ? N3 N3 C6 C3 -177.8(2) 7_647 . . . ? C4 C3 C6 N3 -5.7(3) . . . . ? C2 C3 C6 N3 171.6(2) . . . . ? C1 N1 C5 C4 1.3(3) . . . . ? Zn1 N1 C5 C4 -173.22(19) . . . . ? C3 C4 C5 N1 -1.0(4) . . . . ? O2 N2 O1 Zn1 4.1(3) . . . . ? N1 Zn1 O1 N2 -113.46(19) . . . . ? N1 Zn1 O1 N2 -10.2(3) 2_656 . . . ? O2 Zn1 O1 N2 153.64(18) 2_656 . . . ? O2 Zn1 O1 N2 -2.67(18) . . . . ? O1 Zn1 O1 N2 98.3(2) 2_656 . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.336 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.054 # Attachment 'Z-62_06mz258m.cif' data_06mz258m _database_code_depnum_ccdc_archive 'CCDC 629972' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 N8 O8 Zn2' _chemical_formula_weight 627.15 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 P2(1)/c 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 16.202(4) _cell_length_b 12.591(3) _cell_length_c 11.488(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.283(4) _cell_angle_gamma 90.00 _cell_volume 2343.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6544 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 30.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.778 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 2.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.270 _exptl_absorpt_correction_T_max 0.412 _exptl_absorpt_process_details 'SADABS in SAINT+ (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 15138 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 28.28 _reflns_number_total 5676 _reflns_number_gt 5245 _reflns_threshold_expression >I>2\s(I) _computing_data_collection 'SMART 5.630 (Bruker, 1997-2002)' _computing_cell_refinement 'SAINT+ 6.45 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0837P)^2^+3.2950P] 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 5676 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1374 _refine_ls_wR_factor_gt 0.1230 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 0.5218(3) 0.6406(4) 0.4468(5) 0.0246(10) Uani 1 1 d . . . H1 H 0.5007 0.5747 0.4195 0.030 Uiso 1 1 calc R . . C2 C 0.5837(3) 0.6391(3) 0.5298(5) 0.0228(9) Uani 1 1 d . . . H2 H 0.6050 0.5734 0.5574 0.027 Uiso 1 1 calc R . . C3 C 0.6149(3) 0.7356(3) 0.5734(4) 0.0178(8) Uani 1 1 d . . . C4 C 0.5841(3) 0.8281(3) 0.5232(5) 0.0227(9) Uani 1 1 d . . . H4 H 0.6055 0.8952 0.5461 0.027 Uiso 1 1 calc R . . C5 C 0.5221(3) 0.8224(3) 0.4399(4) 0.0206(9) Uani 1 1 d . . . H5 H 0.5014 0.8867 0.4079 0.025 Uiso 1 1 calc R . . C6 C 0.7918(3) 0.6635(3) 0.7731(4) 0.0184(8) Uani 1 1 d . . . H6 H 0.8297 0.6066 0.7831 0.022 Uiso 1 1 calc R . . C7 C 0.7333(3) 0.6561(3) 0.6850(4) 0.0200(9) Uani 1 1 d . . . H7 H 0.7313 0.5952 0.6362 0.024 Uiso 1 1 calc R . . C8 C 0.6773(3) 0.7391(3) 0.6685(5) 0.0193(9) Uani 1 1 d . . . C9 C 0.6824(3) 0.8253(3) 0.7432(4) 0.0214(9) Uani 1 1 d . . . H9 H 0.6449 0.8829 0.7357 0.026 Uiso 1 1 calc R . . C10 C 0.7429(3) 0.8266(3) 0.8291(4) 0.0217(9) Uani 1 1 d . . . H10 H 0.7459 0.8867 0.8790 0.026 Uiso 1 1 calc R . . C11 C 0.2424(3) 0.6638(3) 0.4475(4) 0.0196(9) Uani 1 1 d . . . H11 H 0.2475 0.6001 0.4037 0.023 Uiso 1 1 calc R . . C12 C 0.1868(3) 0.6667(3) 0.5380(4) 0.0205(9) Uani 1 1 d . . . H12 H 0.1547 0.6059 0.5565 0.025 Uiso 1 1 calc R . . C13 C 0.1782(3) 0.7592(3) 0.6014(4) 0.0202(9) Uani 1 1 d . . . C14 C 0.2261(3) 0.8463(3) 0.5707(4) 0.0203(9) Uani 1 1 d . . . H14 H 0.2211 0.9114 0.6118 0.024 Uiso 1 1 calc R . . C15 C 0.2809(3) 0.8371(3) 0.4797(4) 0.0218(9) Uani 1 1 d . . . H15 H 0.3136 0.8969 0.4595 0.026 Uiso 1 1 calc R . . C16 C 0.0479(2) 0.6789(3) 0.8534(4) 0.0188(8) Uani 1 1 d . . . H16 H 0.0419 0.6197 0.9039 0.023 Uiso 1 1 calc R . . C17 C 0.1090(3) 0.6767(3) 0.7725(4) 0.0206(8) Uani 1 1 d . . . H17 H 0.1445 0.6170 0.7667 0.025 Uiso 1 1 calc R . . C18 C 0.1187(3) 0.7633(3) 0.6985(4) 0.0189(8) Uani 1 1 d . . . C19 C 0.0672(3) 0.8501(3) 0.7129(4) 0.0202(8) Uani 1 1 d . . . H19 H 0.0735 0.9114 0.6655 0.024 Uiso 1 1 calc R . . C20 C 0.0069(3) 0.8464(3) 0.7964(4) 0.0191(8) Uani 1 1 d . . . H20 H -0.0281 0.9062 0.8061 0.023 Uiso 1 1 calc R . . N1 N 0.4900(2) 0.7307(3) 0.4025(4) 0.0185(8) Uani 1 1 d . . . N2 N 0.7973(2) 0.7478(3) 0.8455(4) 0.0193(8) Uani 1 1 d . . . N3 N 0.2899(2) 0.7475(3) 0.4188(4) 0.0175(7) Uani 1 1 d . . . N4 N -0.0042(2) 0.7611(3) 0.8647(4) 0.0186(7) Uani 1 1 d . . . N5 N 0.3838(3) 0.9010(3) 0.1709(4) 0.0282(8) Uani 1 1 d . . . N6 N 0.4005(2) 0.5213(3) 0.2063(4) 0.0282(8) Uani 1 1 d . . . N7 N 0.9197(2) 0.9490(3) 1.0726(4) 0.0281(9) Uani 1 1 d . . . N8 N 0.8766(2) 0.5733(3) 1.0745(4) 0.0241(8) Uani 1 1 d . . . O1 O 0.3869(2) 0.8007(2) 0.1504(3) 0.0284(7) Uani 1 1 d . . . O2 O 0.3816(2) 0.9234(3) 0.2749(3) 0.0301(7) Uani 1 1 d . . . O3 O 0.3563(2) 0.5722(2) 0.2817(3) 0.0275(7) Uani 1 1 d . . . O4 O 0.4556(3) 0.5738(3) 0.1664(4) 0.0470(11) Uani 1 1 d . . . O5 O 0.86829(19) 0.9166(2) 0.9948(3) 0.0242(7) Uani 1 1 d . . . O6 O 0.9678(2) 0.8808(3) 1.1061(4) 0.0381(9) Uani 1 1 d . . . O7 O 0.8659(2) 0.6703(2) 1.1032(3) 0.0281(8) Uani 1 1 d . . . O8 O 0.9024(2) 0.5615(2) 0.9757(3) 0.0264(7) Uani 1 1 d . . . Zn1 Zn 0.38547(3) 0.72527(3) 0.30308(5) 0.01757(13) Uani 1 1 d . . . Zn2 Zn 0.89356(3) 0.76051(3) 0.96495(5) 0.01793(13) 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 0.020(2) 0.0141(19) 0.040(3) 0.0015(18) -0.0024(18) -0.0032(16) C2 0.0169(18) 0.0157(19) 0.036(3) 0.0025(18) 0.0015(18) -0.0006(14) C3 0.0119(18) 0.0176(18) 0.024(2) 0.0020(14) 0.0000(18) 0.0009(16) C4 0.019(2) 0.0124(18) 0.037(3) -0.0024(18) -0.0016(18) 0.0000(14) C5 0.017(2) 0.0124(18) 0.033(3) 0.0017(16) -0.0004(17) 0.0007(15) C6 0.0187(19) 0.0128(17) 0.024(2) 0.0026(15) 0.0014(16) 0.0015(14) C7 0.0174(19) 0.0113(17) 0.031(2) -0.0006(15) 0.0002(17) -0.0020(14) C8 0.0111(18) 0.0138(18) 0.033(3) 0.0022(16) 0.0012(17) -0.0022(14) C9 0.016(2) 0.0180(19) 0.030(2) -0.0010(16) -0.0003(16) 0.0005(15) C10 0.018(2) 0.0153(18) 0.032(2) -0.0038(16) 0.0030(17) 0.0033(15) C11 0.018(2) 0.0137(18) 0.027(2) -0.0029(15) 0.0022(16) -0.0014(15) C12 0.017(2) 0.0135(18) 0.031(2) 0.0003(17) 0.0020(17) -0.0031(14) C13 0.0115(19) 0.0165(19) 0.032(3) 0.0024(17) -0.0032(17) 0.0007(14) C14 0.017(2) 0.0112(17) 0.032(2) -0.0022(16) 0.0004(17) -0.0011(14) C15 0.0168(19) 0.0131(18) 0.035(2) 0.0006(17) 0.0019(18) -0.0031(14) C16 0.0138(19) 0.0131(17) 0.030(2) -0.0002(16) 0.0004(16) 0.0021(14) C17 0.0158(18) 0.0123(16) 0.034(2) -0.0006(15) 0.0000(18) 0.0015(15) C18 0.0106(17) 0.0148(17) 0.031(2) -0.0014(16) 0.0002(18) -0.0010(14) C19 0.0171(19) 0.0129(17) 0.031(2) 0.0014(17) 0.0010(17) -0.0019(14) C20 0.0186(19) 0.0114(17) 0.027(2) 0.0006(16) 0.0006(17) 0.0005(13) N1 0.0133(17) 0.0130(17) 0.029(2) 0.0005(14) -0.0002(14) -0.0006(12) N2 0.0123(16) 0.0145(15) 0.031(2) 0.0026(15) -0.0004(15) 0.0004(13) N3 0.0131(16) 0.0160(15) 0.023(2) 0.0003(15) -0.0018(14) -0.0015(13) N4 0.0128(16) 0.0114(15) 0.032(2) -0.0007(14) 0.0021(15) 0.0008(12) N5 0.0234(18) 0.0203(17) 0.041(2) 0.0090(15) -0.0067(18) -0.0038(16) N6 0.0263(19) 0.0253(18) 0.033(2) -0.0029(16) 0.0075(17) 0.0016(16) N7 0.025(2) 0.0242(19) 0.035(2) -0.0028(17) -0.0011(17) -0.0023(15) N8 0.0238(19) 0.0145(15) 0.034(2) 0.0024(15) 0.0021(16) 0.0010(14) O1 0.0375(18) 0.0189(14) 0.0288(16) 0.0034(13) -0.0013(16) -0.0038(15) O2 0.0324(17) 0.0181(14) 0.040(2) 0.0007(13) 0.0035(17) 0.0050(14) O3 0.0272(16) 0.0147(14) 0.041(2) -0.0042(14) 0.0114(15) -0.0025(12) O4 0.048(2) 0.033(2) 0.061(3) 0.0014(19) 0.032(2) 0.0000(18) O5 0.0213(15) 0.0136(13) 0.0377(19) -0.0026(12) -0.0037(13) 0.0016(11) O6 0.032(2) 0.041(2) 0.041(2) 0.0018(17) -0.0105(16) 0.0065(17) O7 0.038(2) 0.0155(14) 0.0307(18) 0.0019(12) 0.0052(14) 0.0054(12) O8 0.0258(17) 0.0180(14) 0.0354(18) -0.0026(13) 0.0041(15) 0.0030(12) Zn1 0.0120(2) 0.0141(2) 0.0267(3) 0.00162(16) 0.0004(2) -0.00074(16) Zn2 0.0129(2) 0.0134(2) 0.0276(3) 0.00093(17) 0.0008(2) -0.00012(19) _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 1.346(6) . ? C1 C2 1.380(7) . ? C1 H1 0.9500 . ? C2 C3 1.407(6) . ? C2 H2 0.9500 . ? C3 C4 1.391(6) . ? C3 C8 1.487(7) . ? C4 C5 1.386(6) . ? C4 H4 0.9500 . ? C5 N1 1.336(5) . ? C5 H5 0.9500 . ? C6 N2 1.352(6) . ? C6 C7 1.386(6) . ? C6 H6 0.9500 . ? C7 C8 1.395(6) . ? C7 H7 0.9500 . ? C8 C9 1.386(6) . ? C9 C10 1.387(7) . ? C9 H9 0.9500 . ? C10 N2 1.339(5) . ? C10 H10 0.9500 . ? C11 N3 1.347(5) . ? C11 C12 1.380(6) . ? C11 H11 0.9500 . ? C12 C13 1.380(6) . ? C12 H12 0.9500 . ? C13 C14 1.390(6) . ? C13 C18 1.479(6) . ? C14 C15 1.380(6) . ? C14 H14 0.9500 . ? C15 N3 1.335(6) . ? C15 H15 0.9500 . ? C16 N4 1.343(5) . ? C16 C17 1.361(6) . ? C16 H16 0.9500 . ? C17 C18 1.391(6) . ? C17 H17 0.9500 . ? C18 C19 1.385(5) . ? C19 C20 1.373(6) . ? C19 H19 0.9500 . ? C20 N4 1.343(6) . ? C20 H20 0.9500 . ? N1 Zn1 2.038(4) . ? N2 Zn2 2.078(4) . ? N3 Zn1 2.065(4) . ? N4 Zn2 2.022(4) 1_455 ? N5 O2 1.228(6) . ? N5 O1 1.285(5) . ? N6 O4 1.202(6) . ? N6 O3 1.295(5) . ? N7 O6 1.220(6) . ? N7 O5 1.285(5) . ? N8 O8 1.220(5) . ? N8 O7 1.277(5) . ? O1 Zn1 1.995(3) . ? O3 Zn1 2.000(3) . ? O5 Zn2 2.037(3) . ? O7 Zn2 2.005(3) . ? Zn2 N4 2.022(4) 1_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 123.3(4) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C1 C2 C3 119.4(4) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 116.7(4) . . ? C4 C3 C8 121.4(4) . . ? C2 C3 C8 121.9(4) . . ? C5 C4 C3 120.0(4) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? N1 C5 C4 123.2(4) . . ? N1 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? N2 C6 C7 123.0(4) . . ? N2 C6 H6 118.5 . . ? C7 C6 H6 118.5 . . ? C6 C7 C8 119.4(4) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C9 C8 C7 117.8(4) . . ? C9 C8 C3 121.1(4) . . ? C7 C8 C3 121.1(4) . . ? C8 C9 C10 119.3(4) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? N2 C10 C9 123.6(4) . . ? N2 C10 H10 118.2 . . ? C9 C10 H10 118.2 . . ? N3 C11 C12 122.6(4) . . ? N3 C11 H11 118.7 . . ? C12 C11 H11 118.7 . . ? C11 C12 C13 119.2(4) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C12 C13 C14 118.3(4) . . ? C12 C13 C18 119.6(4) . . ? C14 C13 C18 122.1(4) . . ? C15 C14 C13 119.2(4) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? N3 C15 C14 122.6(4) . . ? N3 C15 H15 118.7 . . ? C14 C15 H15 118.7 . . ? N4 C16 C17 122.8(4) . . ? N4 C16 H16 118.6 . . ? C17 C16 H16 118.6 . . ? C16 C17 C18 119.1(4) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C19 C18 C17 118.4(4) . . ? C19 C18 C13 120.8(4) . . ? C17 C18 C13 120.6(4) . . ? C20 C19 C18 119.2(4) . . ? C20 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? N4 C20 C19 122.2(4) . . ? N4 C20 H20 118.9 . . ? C19 C20 H20 118.9 . . ? C5 N1 C1 117.3(4) . . ? C5 N1 Zn1 122.0(3) . . ? C1 N1 Zn1 120.0(3) . . ? C10 N2 C6 117.0(4) . . ? C10 N2 Zn2 121.8(3) . . ? C6 N2 Zn2 120.9(3) . . ? C15 N3 C11 118.0(4) . . ? C15 N3 Zn1 122.3(3) . . ? C11 N3 Zn1 118.8(3) . . ? C20 N4 C16 118.2(4) . . ? C20 N4 Zn2 116.7(3) . 1_455 ? C16 N4 Zn2 124.7(3) . 1_455 ? O2 N5 O1 113.9(4) . . ? O4 N6 O3 113.3(4) . . ? O6 N7 O5 113.9(4) . . ? O8 N8 O7 113.8(4) . . ? N5 O1 Zn1 107.8(3) . . ? N6 O3 Zn1 115.3(3) . . ? N7 O5 Zn2 107.1(3) . . ? N8 O7 Zn2 107.8(3) . . ? O1 Zn1 O3 110.77(14) . . ? O1 Zn1 N1 117.57(16) . . ? O3 Zn1 N1 107.24(14) . . ? O1 Zn1 N3 120.91(16) . . ? O3 Zn1 N3 91.86(14) . . ? N1 Zn1 N3 104.97(16) . . ? O7 Zn2 N4 129.80(15) . 1_655 ? O7 Zn2 O5 111.56(14) . . ? N4 Zn2 O5 104.97(14) 1_655 . ? O7 Zn2 N2 108.02(16) . . ? N4 Zn2 N2 103.80(16) 1_655 . ? O5 Zn2 N2 91.97(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 1.3(7) . . . . ? C1 C2 C3 C4 -4.0(7) . . . . ? C1 C2 C3 C8 175.8(5) . . . . ? C2 C3 C4 C5 3.9(7) . . . . ? C8 C3 C4 C5 -175.9(5) . . . . ? C3 C4 C5 N1 -1.0(7) . . . . ? N2 C6 C7 C8 0.3(7) . . . . ? C6 C7 C8 C9 -0.8(6) . . . . ? C6 C7 C8 C3 178.6(4) . . . . ? C4 C3 C8 C9 27.4(7) . . . . ? C2 C3 C8 C9 -152.3(4) . . . . ? C4 C3 C8 C7 -152.0(4) . . . . ? C2 C3 C8 C7 28.3(7) . . . . ? C7 C8 C9 C10 1.0(7) . . . . ? C3 C8 C9 C10 -178.4(4) . . . . ? C8 C9 C10 N2 -0.7(7) . . . . ? N3 C11 C12 C13 0.7(7) . . . . ? C11 C12 C13 C14 0.4(7) . . . . ? C11 C12 C13 C18 179.9(4) . . . . ? C12 C13 C14 C15 -0.9(7) . . . . ? C18 C13 C14 C15 179.6(4) . . . . ? C13 C14 C15 N3 0.4(7) . . . . ? N4 C16 C17 C18 0.4(7) . . . . ? C16 C17 C18 C19 2.1(7) . . . . ? C16 C17 C18 C13 -173.3(4) . . . . ? C12 C13 C18 C19 -136.0(5) . . . . ? C14 C13 C18 C19 43.5(6) . . . . ? C12 C13 C18 C17 39.4(6) . . . . ? C14 C13 C18 C17 -141.1(5) . . . . ? C17 C18 C19 C20 -2.2(7) . . . . ? C13 C18 C19 C20 173.3(4) . . . . ? C18 C19 C20 N4 -0.3(7) . . . . ? C4 C5 N1 C1 -1.8(7) . . . . ? C4 C5 N1 Zn1 168.5(4) . . . . ? C2 C1 N1 C5 1.7(7) . . . . ? C2 C1 N1 Zn1 -168.9(4) . . . . ? C9 C10 N2 C6 0.1(7) . . . . ? C9 C10 N2 Zn2 174.0(4) . . . . ? C7 C6 N2 C10 0.0(7) . . . . ? C7 C6 N2 Zn2 -173.8(3) . . . . ? C14 C15 N3 C11 0.7(7) . . . . ? C14 C15 N3 Zn1 -168.9(3) . . . . ? C12 C11 N3 C15 -1.3(7) . . . . ? C12 C11 N3 Zn1 168.7(3) . . . . ? C19 C20 N4 C16 2.8(7) . . . . ? C19 C20 N4 Zn2 -170.8(3) . . . 1_455 ? C17 C16 N4 C20 -2.9(7) . . . . ? C17 C16 N4 Zn2 170.1(3) . . . 1_455 ? O2 N5 O1 Zn1 0.7(5) . . . . ? O4 N6 O3 Zn1 4.3(6) . . . . ? O6 N7 O5 Zn2 0.2(5) . . . . ? O8 N8 O7 Zn2 2.2(5) . . . . ? N5 O1 Zn1 O3 163.0(3) . . . . ? N5 O1 Zn1 N1 -73.2(4) . . . . ? N5 O1 Zn1 N3 57.5(4) . . . . ? N6 O3 Zn1 O1 52.6(4) . . . . ? N6 O3 Zn1 N1 -76.9(3) . . . . ? N6 O3 Zn1 N3 176.8(3) . . . . ? C5 N1 Zn1 O1 59.6(4) . . . . ? C1 N1 Zn1 O1 -130.3(4) . . . . ? C5 N1 Zn1 O3 -174.9(4) . . . . ? C1 N1 Zn1 O3 -4.8(4) . . . . ? C5 N1 Zn1 N3 -78.1(4) . . . . ? C1 N1 Zn1 N3 92.0(4) . . . . ? C15 N3 Zn1 O1 -72.7(4) . . . . ? C11 N3 Zn1 O1 117.7(3) . . . . ? C15 N3 Zn1 O3 171.6(4) . . . . ? C11 N3 Zn1 O3 2.1(4) . . . . ? C15 N3 Zn1 N1 63.2(4) . . . . ? C11 N3 Zn1 N1 -106.3(3) . . . . ? N8 O7 Zn2 N4 -51.8(4) . . . 1_655 ? N8 O7 Zn2 O5 174.5(3) . . . . ? N8 O7 Zn2 N2 74.9(3) . . . . ? N7 O5 Zn2 O7 68.0(3) . . . . ? N7 O5 Zn2 N4 -76.8(3) . . . 1_655 ? N7 O5 Zn2 N2 178.3(3) . . . . ? C10 N2 Zn2 O7 105.7(4) . . . . ? C6 N2 Zn2 O7 -80.7(4) . . . . ? C10 N2 Zn2 N4 -113.7(4) . . . 1_655 ? C6 N2 Zn2 N4 59.9(4) . . . 1_655 ? C10 N2 Zn2 O5 -7.8(4) . . . . ? C6 N2 Zn2 O5 165.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 2.193 _refine_diff_density_min -1.016 _refine_diff_density_rms 0.135 data_06mz297m _database_code_depnum_ccdc_archive 'CCDC 629973' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 N4 O4 Zn' _chemical_formula_weight 355.67 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(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.3273(8) _cell_length_b 15.0682(12) _cell_length_c 19.0674(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2967.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8206 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 30.52 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 1.679 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.390 _exptl_absorpt_correction_T_max 0.511 _exptl_absorpt_process_details 'SADABS in SAINT+ (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 31184 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 28.28 _reflns_number_total 7376 _reflns_number_gt 7075 _reflns_threshold_expression >I>2\s(I) _computing_data_collection 'SMART 5.630 (Bruker, 1997-2002)' _computing_cell_refinement 'SAINT+ 6.45 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0384P)^2^+0.3930P] 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, 3256 Friedel pairs' _refine_ls_abs_structure_Flack 0.377(6) _refine_ls_number_reflns 7376 _refine_ls_number_parameters 398 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0246 _refine_ls_wR_factor_ref 0.0622 _refine_ls_wR_factor_gt 0.0613 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 C1 C 0.77459(17) 0.73604(12) 0.83861(9) 0.0201(3) Uani 1 1 d . . . H1 H 0.7391 0.7916 0.8250 0.024 Uiso 1 1 calc R . . C2 C 0.88727(17) 0.70790(12) 0.80696(8) 0.0195(3) Uani 1 1 d . . . H2 H 0.9281 0.7440 0.7726 0.023 Uiso 1 1 calc R . . C3 C 0.94155(16) 0.62610(11) 0.82547(8) 0.0170(3) Uani 1 1 d . . . C4 C 0.87516(17) 0.57627(12) 0.87507(9) 0.0209(3) Uani 1 1 d . . . H4 H 0.9069 0.5196 0.8884 0.025 Uiso 1 1 calc R . . C5 C 0.76307(17) 0.60884(12) 0.90510(9) 0.0211(3) Uani 1 1 d . . . H5 H 0.7199 0.5737 0.9393 0.025 Uiso 1 1 calc R . . C6 C 1.06834(16) 0.59742(12) 0.79355(8) 0.0198(3) Uani 1 1 d . . . H6A H 1.1110 0.5548 0.8256 0.024 Uiso 1 1 calc R . . H6B H 1.1255 0.6499 0.7891 0.024 Uiso 1 1 calc R . . C7 C 1.05327(18) 0.55379(11) 0.72074(8) 0.0207(3) Uani 1 1 d . . . H7A H 0.9975 0.5918 0.6911 0.025 Uiso 1 1 calc R . . H7B H 1.1393 0.5500 0.6981 0.025 Uiso 1 1 calc R . . C8 C 0.99435(18) 0.46086(12) 0.72458(9) 0.0209(3) Uani 1 1 d . . . H8A H 1.0481 0.4241 0.7563 0.025 Uiso 1 1 calc R . . H8B H 0.9070 0.4654 0.7457 0.025 Uiso 1 1 calc R . . C9 C 1.06662(16) 0.37247(12) 0.54191(9) 0.0201(3) Uani 1 1 d . . . H9 H 1.1336 0.3773 0.5080 0.024 Uiso 1 1 calc R . . C10 C 1.07876(16) 0.41931(12) 0.60382(9) 0.0202(3) Uani 1 1 d . . . H10 H 1.1527 0.4555 0.6116 0.024 Uiso 1 1 calc R . . C11 C 0.98273(17) 0.41361(11) 0.65488(9) 0.0193(3) Uani 1 1 d . . . C12 C 0.87740(17) 0.35839(12) 0.64007(9) 0.0211(3) Uani 1 1 d . . . H12 H 0.8099 0.3517 0.6735 0.025 Uiso 1 1 calc R . . C13 C 0.87118(17) 0.31365(12) 0.57708(9) 0.0210(3) Uani 1 1 d . . . H13 H 0.7985 0.2766 0.5682 0.025 Uiso 1 1 calc R . . C14 C 0.47073(17) 0.67581(12) 0.58050(9) 0.0221(3) Uani 1 1 d . . . H14 H 0.3995 0.7128 0.5687 0.027 Uiso 1 1 calc R . . C15 C 0.47509(17) 0.63911(13) 0.64635(9) 0.0237(4) Uani 1 1 d . . . H15 H 0.4080 0.6509 0.6792 0.028 Uiso 1 1 calc R . . C16 C 0.57889(16) 0.58431(12) 0.66484(9) 0.0201(3) Uani 1 1 d . . . C17 C 0.67418(16) 0.57002(12) 0.61471(9) 0.0205(3) Uani 1 1 d . . . H17 H 0.7466 0.5335 0.6253 0.025 Uiso 1 1 calc R . . C18 C 0.66316(16) 0.60921(12) 0.54928(9) 0.0209(3) Uani 1 1 d . . . H18 H 0.7290 0.5986 0.5155 0.025 Uiso 1 1 calc R . . C19 C 0.58881(17) 0.54256(13) 0.73696(9) 0.0244(4) Uani 1 1 d . . . H19A H 0.6088 0.5896 0.7716 0.029 Uiso 1 1 calc R . . H19B H 0.6618 0.5000 0.7370 0.029 Uiso 1 1 calc R . . C20 C 0.46622(17) 0.49422(12) 0.76010(9) 0.0215(3) Uani 1 1 d . . . H20A H 0.4449 0.4473 0.7256 0.026 Uiso 1 1 calc R . . H20B H 0.3931 0.5366 0.7615 0.026 Uiso 1 1 calc R . . C21 C 0.48426(17) 0.45237(14) 0.83279(10) 0.0268(4) Uani 1 1 d . . . H21A H 0.5521 0.4060 0.8303 0.032 Uiso 1 1 calc R . . H21B H 0.5133 0.4984 0.8664 0.032 Uiso 1 1 calc R . . C22 C 0.16321(16) 0.41922(11) 0.92530(9) 0.0194(3) Uani 1 1 d . . . H22 H 0.1090 0.4514 0.9565 0.023 Uiso 1 1 calc R . . C23 C 0.27810(17) 0.45790(12) 0.90340(9) 0.0217(3) Uani 1 1 d . . . H23 H 0.3009 0.5157 0.9191 0.026 Uiso 1 1 calc R . . C24 C 0.35981(17) 0.41185(12) 0.85835(9) 0.0207(3) Uani 1 1 d . . . C25 C 0.32055(17) 0.32779(13) 0.83679(9) 0.0217(3) Uani 1 1 d . . . H25 H 0.3735 0.2940 0.8060 0.026 Uiso 1 1 calc R . . C26 C 0.20421(17) 0.29366(11) 0.86029(8) 0.0196(3) Uani 1 1 d . . . H26 H 0.1786 0.2364 0.8448 0.024 Uiso 1 1 calc R . . N1 N 0.52510(16) 0.91113(11) 0.96494(9) 0.0284(3) Uani 1 1 d . . . N2 N 0.39486(16) 0.71371(12) 0.82150(8) 0.0259(3) Uani 1 1 d . . . N3 N 0.71243(14) 0.68823(10) 0.88794(7) 0.0182(3) Uani 1 1 d . . . N4 N 0.96406(14) 0.32024(9) 0.52748(7) 0.0186(3) Uani 1 1 d . . . N5 N 0.56805(17) 0.88580(11) 0.46360(9) 0.0289(4) Uani 1 1 d . . . N6 N 0.69471(15) 0.67602(12) 0.32584(8) 0.0251(3) Uani 1 1 d . . . N7 N 0.56325(14) 0.66159(10) 0.53170(7) 0.0196(3) Uani 1 1 d . . . N8 N 0.12538(14) 0.33831(10) 0.90432(7) 0.0172(3) Uani 1 1 d . . . O1 O 0.62740(13) 0.86666(10) 0.95403(8) 0.0300(3) Uani 1 1 d . . . O2 O 0.42535(13) 0.86617(10) 0.95792(8) 0.0304(3) Uani 1 1 d . . . O3 O 0.47887(14) 0.77111(9) 0.81297(7) 0.0283(3) Uani 1 1 d . . . O4 O 0.39640(13) 0.67911(9) 0.88316(7) 0.0239(3) Uani 1 1 d . . . O5 O 0.46418(14) 0.84436(9) 0.45353(7) 0.0297(3) Uani 1 1 d . . . O6 O 0.66587(14) 0.83763(10) 0.45617(8) 0.0319(3) Uani 1 1 d . . . O7 O 0.69925(13) 0.64551(9) 0.38832(7) 0.0263(3) Uani 1 1 d . . . O8 O 0.60732(13) 0.73220(9) 0.31804(7) 0.0267(3) Uani 1 1 d . . . Zn1 Zn 0.547666(18) 0.742831(12) 0.932072(10) 0.01825(5) Uani 1 1 d . . . Zn2 Zn 0.548099(18) 0.718171(12) 0.434309(9) 0.01728(5) 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 0.0229(8) 0.0180(8) 0.0195(8) -0.0002(6) -0.0006(6) -0.0012(6) C2 0.0231(8) 0.0192(8) 0.0163(8) 0.0001(6) 0.0015(6) -0.0022(7) C3 0.0185(7) 0.0196(7) 0.0130(7) -0.0044(6) -0.0017(6) -0.0016(7) C4 0.0247(8) 0.0197(8) 0.0182(8) 0.0017(6) -0.0027(6) 0.0020(7) C5 0.0244(8) 0.0226(8) 0.0163(8) 0.0023(6) -0.0008(6) -0.0020(7) C6 0.0175(8) 0.0226(8) 0.0194(8) -0.0021(6) 0.0009(6) 0.0015(6) C7 0.0241(8) 0.0202(8) 0.0179(7) -0.0013(6) 0.0034(7) 0.0003(7) C8 0.0258(8) 0.0196(8) 0.0171(7) 0.0000(6) 0.0022(6) 0.0011(7) C9 0.0188(8) 0.0222(8) 0.0193(7) 0.0013(6) 0.0023(6) -0.0007(6) C10 0.0204(8) 0.0196(8) 0.0206(8) 0.0001(6) -0.0001(6) -0.0016(6) C11 0.0233(8) 0.0155(7) 0.0190(8) 0.0014(6) -0.0010(6) 0.0030(6) C12 0.0189(8) 0.0243(8) 0.0200(8) 0.0019(7) 0.0027(6) 0.0023(7) C13 0.0183(7) 0.0228(8) 0.0220(8) 0.0011(7) 0.0011(6) -0.0005(6) C14 0.0194(8) 0.0255(8) 0.0214(8) 0.0023(6) -0.0010(6) 0.0011(7) C15 0.0202(8) 0.0307(9) 0.0202(8) 0.0013(7) 0.0024(6) -0.0006(7) C16 0.0200(8) 0.0223(8) 0.0179(8) 0.0023(6) -0.0015(6) -0.0055(6) C17 0.0197(8) 0.0206(8) 0.0213(8) 0.0013(6) -0.0020(6) 0.0004(6) C18 0.0206(8) 0.0241(8) 0.0181(8) 0.0004(6) 0.0013(6) 0.0003(7) C19 0.0212(8) 0.0311(9) 0.0211(8) 0.0073(7) -0.0016(6) -0.0042(7) C20 0.0206(8) 0.0249(8) 0.0190(8) 0.0053(6) -0.0011(6) -0.0045(7) C21 0.0211(9) 0.0342(10) 0.0252(9) 0.0120(8) -0.0026(7) -0.0049(7) C22 0.0235(8) 0.0194(8) 0.0152(7) 0.0005(6) -0.0011(6) 0.0015(6) C23 0.0254(8) 0.0187(8) 0.0210(8) 0.0025(7) -0.0039(7) -0.0028(7) C24 0.0200(8) 0.0273(9) 0.0149(7) 0.0087(7) -0.0028(6) -0.0011(7) C25 0.0221(8) 0.0249(9) 0.0181(8) 0.0034(7) 0.0026(6) 0.0049(7) C26 0.0249(8) 0.0181(7) 0.0158(7) 0.0006(6) -0.0011(6) 0.0017(7) N1 0.0260(8) 0.0260(8) 0.0332(8) -0.0056(7) 0.0009(6) 0.0007(6) N2 0.0241(8) 0.0319(8) 0.0216(7) -0.0010(6) -0.0007(6) 0.0037(7) N3 0.0189(7) 0.0198(7) 0.0159(6) -0.0015(5) -0.0010(5) -0.0011(5) N4 0.0188(7) 0.0198(6) 0.0171(6) 0.0008(5) -0.0010(5) 0.0004(6) N5 0.0388(10) 0.0212(7) 0.0267(8) -0.0003(6) -0.0060(7) -0.0028(7) N6 0.0265(8) 0.0302(8) 0.0184(7) -0.0007(6) 0.0013(6) -0.0028(7) N7 0.0197(7) 0.0218(7) 0.0173(6) 0.0000(5) -0.0012(5) -0.0017(6) N8 0.0194(7) 0.0186(7) 0.0136(6) 0.0021(5) -0.0011(5) 0.0008(5) O1 0.0244(7) 0.0255(7) 0.0400(8) -0.0015(6) 0.0035(6) 0.0001(5) O2 0.0225(7) 0.0332(7) 0.0354(7) -0.0077(6) 0.0000(5) -0.0007(6) O3 0.0259(7) 0.0336(8) 0.0253(7) 0.0063(6) 0.0011(5) 0.0007(5) O4 0.0245(6) 0.0271(7) 0.0200(6) 0.0013(5) -0.0011(5) -0.0015(5) O5 0.0291(7) 0.0247(6) 0.0353(7) -0.0008(5) -0.0069(6) 0.0008(6) O6 0.0268(7) 0.0337(8) 0.0353(8) -0.0062(6) -0.0004(6) -0.0057(6) O7 0.0292(7) 0.0296(7) 0.0200(6) 0.0025(5) 0.0002(5) 0.0047(6) O8 0.0258(7) 0.0308(7) 0.0234(6) 0.0032(6) -0.0018(5) 0.0007(5) Zn1 0.01822(9) 0.01965(9) 0.01688(9) -0.00054(7) 0.00124(8) -0.00024(7) Zn2 0.01820(9) 0.01855(9) 0.01510(9) 0.00009(7) -0.00090(8) -0.00131(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 N3 1.348(2) . ? C1 C2 1.378(2) . ? C1 H1 0.9500 . ? C2 C3 1.399(2) . ? C2 H2 0.9500 . ? C3 C4 1.389(2) . ? C3 C6 1.507(2) . ? C4 C5 1.382(2) . ? C4 H4 0.9500 . ? C5 N3 1.346(2) . ? C5 H5 0.9500 . ? C6 C7 1.544(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.529(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C11 1.512(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N4 1.348(2) . ? C9 C10 1.381(2) . ? C9 H9 0.9500 . ? C10 C11 1.392(2) . ? C10 H10 0.9500 . ? C11 C12 1.398(2) . ? C12 C13 1.379(2) . ? C12 H12 0.9500 . ? C13 N4 1.351(2) . ? C13 H13 0.9500 . ? C14 N7 1.351(2) . ? C14 C15 1.373(2) . ? C14 H14 0.9500 . ? C15 C16 1.398(2) . ? C15 H15 0.9500 . ? C16 C17 1.389(2) . ? C16 C19 1.516(2) . ? C17 C18 1.385(2) . ? C17 H17 0.9500 . ? C18 N7 1.342(2) . ? C18 H18 0.9500 . ? C19 C20 1.526(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.534(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C24 1.504(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 N8 1.341(2) . ? C22 C23 1.386(2) . ? C22 H22 0.9500 . ? C23 C24 1.390(3) . ? C23 H23 0.9500 . ? C24 C25 1.392(3) . ? C25 C26 1.382(2) . ? C25 H25 0.9500 . ? C26 N8 1.349(2) . ? C26 H26 0.9500 . ? N1 O2 1.240(2) . ? N1 O1 1.268(2) . ? N2 O3 1.236(2) . ? N2 O4 1.286(2) . ? N3 Zn1 2.0689(15) . ? N4 Zn1 2.0560(14) 2_664 ? N5 O6 1.252(2) . ? N5 O5 1.256(2) . ? N6 O8 1.246(2) . ? N6 O7 1.278(2) . ? N7 Zn2 2.0494(14) . ? N8 Zn2 2.0642(15) 2_565 ? O1 Zn1 2.0820(15) . ? O2 Zn1 2.3006(15) . ? O3 Zn1 2.4173(13) . ? O4 Zn1 2.0572(13) . ? O5 Zn2 2.1216(14) . ? O6 Zn2 2.2120(15) . ? O7 Zn2 2.0987(13) . ? O8 Zn2 2.3095(13) . ? Zn1 N4 2.0560(14) 2_665 ? Zn2 N8 2.0642(15) 2_564 ? 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 N3 C1 C2 122.92(16) . . ? N3 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 119.94(16) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 116.77(16) . . ? C4 C3 C6 123.29(15) . . ? C2 C3 C6 119.91(15) . . ? C5 C4 C3 120.25(16) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? N3 C5 C4 122.73(16) . . ? N3 C5 H5 118.6 . . ? C4 C5 H5 118.6 . . ? C3 C6 C7 113.43(14) . . ? C3 C6 H6A 108.9 . . ? C7 C6 H6A 108.9 . . ? C3 C6 H6B 108.9 . . ? C7 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? C8 C7 C6 112.78(14) . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C11 C8 C7 114.88(14) . . ? C11 C8 H8A 108.5 . . ? C7 C8 H8A 108.5 . . ? C11 C8 H8B 108.5 . . ? C7 C8 H8B 108.5 . . ? H8A C8 H8B 107.5 . . ? N4 C9 C10 122.97(15) . . ? N4 C9 H9 118.5 . . ? C10 C9 H9 118.5 . . ? C9 C10 C11 120.09(16) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C12 116.72(16) . . ? C10 C11 C8 121.93(15) . . ? C12 C11 C8 121.28(15) . . ? C13 C12 C11 120.20(16) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? N4 C13 C12 122.75(16) . . ? N4 C13 H13 118.6 . . ? C12 C13 H13 118.6 . . ? N7 C14 C15 122.88(16) . . ? N7 C14 H14 118.6 . . ? C15 C14 H14 118.6 . . ? C14 C15 C16 119.58(16) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C17 C16 C15 117.48(16) . . ? C17 C16 C19 120.81(16) . . ? C15 C16 C19 121.71(15) . . ? C18 C17 C16 119.71(16) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? N7 C18 C17 122.63(16) . . ? N7 C18 H18 118.7 . . ? C17 C18 H18 118.7 . . ? C16 C19 C20 113.85(14) . . ? C16 C19 H19A 108.8 . . ? C20 C19 H19A 108.8 . . ? C16 C19 H19B 108.8 . . ? C20 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? C19 C20 C21 110.90(14) . . ? C19 C20 H20A 109.5 . . ? C21 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? C21 C20 H20B 109.5 . . ? H20A C20 H20B 108.0 . . ? C24 C21 C20 110.85(14) . . ? C24 C21 H21A 109.5 . . ? C20 C21 H21A 109.5 . . ? C24 C21 H21B 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 108.1 . . ? N8 C22 C23 122.79(16) . . ? N8 C22 H22 118.6 . . ? C23 C22 H22 118.6 . . ? C22 C23 C24 119.74(16) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C23 C24 C25 117.38(16) . . ? C23 C24 C21 121.10(17) . . ? C25 C24 C21 121.50(17) . . ? C26 C25 C24 119.75(17) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? N8 C26 C25 122.75(16) . . ? N8 C26 H26 118.6 . . ? C25 C26 H26 118.6 . . ? O2 N1 O1 112.68(15) . . ? O3 N2 O4 113.29(15) . . ? C5 N3 C1 117.37(15) . . ? C5 N3 Zn1 125.04(12) . . ? C1 N3 Zn1 117.59(12) . . ? C9 N4 C13 117.26(14) . . ? C9 N4 Zn1 119.79(11) . 2_664 ? C13 N4 Zn1 122.94(12) . 2_664 ? O6 N5 O5 112.56(15) . . ? O8 N6 O7 112.47(15) . . ? C18 N7 C14 117.72(14) . . ? C18 N7 Zn2 122.00(11) . . ? C14 N7 Zn2 120.28(12) . . ? C22 N8 C26 117.59(15) . . ? C22 N8 Zn2 123.02(12) . 2_565 ? C26 N8 Zn2 119.37(12) . 2_565 ? N1 O1 Zn1 100.20(11) . . ? N1 O2 Zn1 90.48(10) . . ? N2 O3 Zn1 87.67(10) . . ? N2 O4 Zn1 103.57(11) . . ? N5 O5 Zn2 97.07(11) . . ? N5 O6 Zn2 92.83(11) . . ? N6 O7 Zn2 100.06(11) . . ? N6 O8 Zn2 90.86(10) . . ? N4 Zn1 O4 98.09(6) 2_665 . ? N4 Zn1 N3 102.97(6) 2_665 . ? O4 Zn1 N3 104.75(5) . . ? N4 Zn1 O1 105.05(6) 2_665 . ? O4 Zn1 O1 144.08(6) . . ? N3 Zn1 O1 96.48(6) . . ? N4 Zn1 O2 98.71(6) 2_665 . ? O4 Zn1 O2 93.28(5) . . ? N3 Zn1 O2 149.32(6) . . ? O1 Zn1 O2 56.64(5) . . ? N4 Zn1 O3 153.56(5) 2_665 . ? O4 Zn1 O3 55.47(5) . . ? N3 Zn1 O3 85.97(5) . . ? O1 Zn1 O3 98.47(5) . . ? O2 Zn1 O3 84.12(5) . . ? N7 Zn2 N8 98.38(6) . 2_564 ? N7 Zn2 O7 96.02(5) . . ? N8 Zn2 O7 108.35(6) 2_564 . ? N7 Zn2 O5 104.33(6) . . ? N8 Zn2 O5 93.60(6) 2_564 . ? O7 Zn2 O5 147.52(6) . . ? N7 Zn2 O6 97.23(6) . . ? N8 Zn2 O6 149.87(6) 2_564 . ? O7 Zn2 O6 95.41(6) . . ? O5 Zn2 O6 57.50(6) . . ? N7 Zn2 O8 152.59(5) . . ? N8 Zn2 O8 90.10(5) 2_564 . ? O7 Zn2 O8 56.61(5) . . ? O5 Zn2 O8 101.07(5) . . ? O6 Zn2 O8 87.75(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C1 C2 C3 0.4(3) . . . . ? C1 C2 C3 C4 1.2(2) . . . . ? C1 C2 C3 C6 -176.91(15) . . . . ? C2 C3 C4 C5 -1.7(2) . . . . ? C6 C3 C4 C5 176.34(15) . . . . ? C3 C4 C5 N3 0.7(3) . . . . ? C4 C3 C6 C7 98.55(19) . . . . ? C2 C3 C6 C7 -83.48(19) . . . . ? C3 C6 C7 C8 -72.35(19) . . . . ? C6 C7 C8 C11 -177.53(15) . . . . ? N4 C9 C10 C11 0.2(3) . . . . ? C9 C10 C11 C12 0.6(3) . . . . ? C9 C10 C11 C8 177.58(16) . . . . ? C7 C8 C11 C10 39.3(2) . . . . ? C7 C8 C11 C12 -143.93(17) . . . . ? C10 C11 C12 C13 -0.8(3) . . . . ? C8 C11 C12 C13 -177.79(16) . . . . ? C11 C12 C13 N4 0.2(3) . . . . ? N7 C14 C15 C16 -0.1(3) . . . . ? C14 C15 C16 C17 0.3(3) . . . . ? C14 C15 C16 C19 179.64(17) . . . . ? C15 C16 C17 C18 -0.4(3) . . . . ? C19 C16 C17 C18 -179.74(16) . . . . ? C16 C17 C18 N7 0.3(3) . . . . ? C17 C16 C19 C20 -130.10(18) . . . . ? C15 C16 C19 C20 50.6(2) . . . . ? C16 C19 C20 C21 178.98(16) . . . . ? C19 C20 C21 C24 174.89(16) . . . . ? N8 C22 C23 C24 -0.7(3) . . . . ? C22 C23 C24 C25 0.5(2) . . . . ? C22 C23 C24 C21 179.14(15) . . . . ? C20 C21 C24 C23 -96.9(2) . . . . ? C20 C21 C24 C25 81.8(2) . . . . ? C23 C24 C25 C26 0.0(2) . . . . ? C21 C24 C25 C26 -178.62(15) . . . . ? C24 C25 C26 N8 -0.4(3) . . . . ? C4 C5 N3 C1 0.9(2) . . . . ? C4 C5 N3 Zn1 -178.52(13) . . . . ? C2 C1 N3 C5 -1.4(3) . . . . ? C2 C1 N3 Zn1 178.03(13) . . . . ? C10 C9 N4 C13 -0.9(2) . . . . ? C10 C9 N4 Zn1 177.65(13) . . . 2_664 ? C12 C13 N4 C9 0.7(2) . . . . ? C12 C13 N4 Zn1 -177.80(13) . . . 2_664 ? C17 C18 N7 C14 0.0(3) . . . . ? C17 C18 N7 Zn2 -179.52(13) . . . . ? C15 C14 N7 C18 -0.1(3) . . . . ? C15 C14 N7 Zn2 179.43(14) . . . . ? C23 C22 N8 C26 0.3(2) . . . . ? C23 C22 N8 Zn2 -178.09(12) . . . 2_565 ? C25 C26 N8 C22 0.2(2) . . . . ? C25 C26 N8 Zn2 178.70(12) . . . 2_565 ? O2 N1 O1 Zn1 -0.62(17) . . . . ? O1 N1 O2 Zn1 0.56(15) . . . . ? O4 N2 O3 Zn1 0.64(14) . . . . ? O3 N2 O4 Zn1 -0.77(17) . . . . ? O6 N5 O5 Zn2 1.83(16) . . . . ? O5 N5 O6 Zn2 -1.74(15) . . . . ? O8 N6 O7 Zn2 -0.58(16) . . . . ? O7 N6 O8 Zn2 0.52(15) . . . . ? N2 O4 Zn1 N4 -179.72(11) . . . 2_665 ? N2 O4 Zn1 N3 -73.94(11) . . . . ? N2 O4 Zn1 O1 50.27(15) . . . . ? N2 O4 Zn1 O2 80.99(11) . . . . ? N2 O4 Zn1 O3 0.44(9) . . . . ? C5 N3 Zn1 N4 23.46(15) . . . 2_665 ? C1 N3 Zn1 N4 -155.97(12) . . . 2_665 ? C5 N3 Zn1 O4 -78.65(14) . . . . ? C1 N3 Zn1 O4 101.91(13) . . . . ? C5 N3 Zn1 O1 130.57(14) . . . . ? C1 N3 Zn1 O1 -48.86(13) . . . . ? C5 N3 Zn1 O2 157.32(13) . . . . ? C1 N3 Zn1 O2 -22.11(19) . . . . ? C5 N3 Zn1 O3 -131.35(14) . . . . ? C1 N3 Zn1 O3 49.22(13) . . . . ? N1 O1 Zn1 N4 -90.25(12) . . . 2_665 ? N1 O1 Zn1 O4 38.01(16) . . . . ? N1 O1 Zn1 N3 164.41(11) . . . . ? N1 O1 Zn1 O2 0.37(10) . . . . ? N1 O1 Zn1 O3 77.54(12) . . . . ? N1 O2 Zn1 N4 101.95(11) . . . 2_665 ? N1 O2 Zn1 O4 -159.34(11) . . . . ? N1 O2 Zn1 N3 -32.74(17) . . . . ? N1 O2 Zn1 O1 -0.37(10) . . . . ? N1 O2 Zn1 O3 -104.56(11) . . . . ? N2 O3 Zn1 N4 -0.79(17) . . . 2_665 ? N2 O3 Zn1 O4 -0.44(10) . . . . ? N2 O3 Zn1 N3 110.54(11) . . . . ? N2 O3 Zn1 O1 -153.49(10) . . . . ? N2 O3 Zn1 O2 -98.54(10) . . . . ? C18 N7 Zn2 N8 119.80(14) . . . 2_564 ? C14 N7 Zn2 N8 -59.69(14) . . . 2_564 ? C18 N7 Zn2 O7 10.20(14) . . . . ? C14 N7 Zn2 O7 -169.29(13) . . . . ? C18 N7 Zn2 O5 -144.28(13) . . . . ? C14 N7 Zn2 O5 36.23(14) . . . . ? C18 N7 Zn2 O6 -86.05(14) . . . . ? C14 N7 Zn2 O6 94.46(13) . . . . ? C18 N7 Zn2 O8 13.1(2) . . . . ? C14 N7 Zn2 O8 -166.41(12) . . . . ? N6 O7 Zn2 N7 178.76(11) . . . . ? N6 O7 Zn2 N8 77.85(11) . . . 2_564 ? N6 O7 Zn2 O5 -52.26(16) . . . . ? N6 O7 Zn2 O6 -83.36(11) . . . . ? N6 O7 Zn2 O8 0.35(10) . . . . ? N5 O5 Zn2 N7 88.37(11) . . . . ? N5 O5 Zn2 N8 -172.03(11) . . . 2_564 ? N5 O5 Zn2 O7 -38.70(16) . . . . ? N5 O5 Zn2 O6 -1.13(10) . . . . ? N5 O5 Zn2 O8 -81.23(11) . . . . ? N5 O6 Zn2 N7 -101.29(11) . . . . ? N5 O6 Zn2 N8 19.46(17) . . . 2_564 ? N5 O6 Zn2 O7 161.93(11) . . . . ? N5 O6 Zn2 O5 1.13(10) . . . . ? N5 O6 Zn2 O8 105.77(11) . . . . ? N6 O8 Zn2 N7 -3.78(17) . . . . ? N6 O8 Zn2 N8 -112.43(11) . . . 2_564 ? N6 O8 Zn2 O7 -0.35(10) . . . . ? N6 O8 Zn2 O5 153.88(10) . . . . ? N6 O8 Zn2 O6 97.63(11) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.795 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.070 # Attachment 'Z-69_06mz281m.cif' data_06mz281m _database_code_depnum_ccdc_archive 'CCDC 629974' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 N12 O9 Zn2' _chemical_formula_weight 753.28 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 P2(1)/c 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 6.7562(3) _cell_length_b 13.1951(7) _cell_length_c 33.5642(17) _cell_angle_alpha 90.00 _cell_angle_beta 94.2630(10) _cell_angle_gamma 90.00 _cell_volume 2983.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5395 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 30.47 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.677 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 1.681 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.635 _exptl_absorpt_correction_T_max 0.751 _exptl_absorpt_process_details 'SADABS in SAINT+ (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 19944 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 28.28 _reflns_number_total 7323 _reflns_number_gt 6496 _reflns_threshold_expression >I>2\s(I) _computing_data_collection 'SMART 5.630 (Bruker, 1997-2002)' _computing_cell_refinement 'SAINT+ 6.45 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0508P)^2^+6.0980P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7323 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1160 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.081 _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 1.7806(4) 0.4379(2) 0.71681(9) 0.0200(6) Uani 1 1 d . . . H1 H 1.9016 0.4316 0.7330 0.024 Uiso 1 1 calc R . . C2 C 1.7234(5) 0.3596(2) 0.69106(10) 0.0225(6) Uani 1 1 d . . . H2 H 1.8048 0.3012 0.6894 0.027 Uiso 1 1 calc R . . C3 C 1.5473(5) 0.3672(2) 0.66786(9) 0.0203(6) Uani 1 1 d . . . H3 H 1.5062 0.3144 0.6498 0.024 Uiso 1 1 calc R . . C4 C 1.4299(4) 0.4534(2) 0.67115(8) 0.0173(6) Uani 1 1 d . . . C5 C 1.4992(4) 0.5290(2) 0.69713(8) 0.0166(5) Uani 1 1 d . . . H5 H 1.4214 0.5885 0.6991 0.020 Uiso 1 1 calc R . . C6 C 1.2354(4) 0.4676(2) 0.64974(9) 0.0198(6) Uani 1 1 d . . . H6 H 1.1667 0.5296 0.6528 0.024 Uiso 1 1 calc R . . C7 C 0.8819(5) 0.3663(2) 0.58729(9) 0.0236(6) Uani 1 1 d . . . H7 H 0.9428 0.3028 0.5828 0.028 Uiso 1 1 calc R . . C8 C 0.3222(4) 0.4319(2) 0.52986(9) 0.0203(6) Uani 1 1 d . . . H8 H 0.1968 0.4467 0.5164 0.024 Uiso 1 1 calc R . . C9 C 0.4135(5) 0.5054(2) 0.55429(10) 0.0248(7) Uani 1 1 d . . . H9 H 0.3513 0.5690 0.5579 0.030 Uiso 1 1 calc R . . C10 C 0.5972(5) 0.4843(2) 0.57338(9) 0.0231(6) Uani 1 1 d . . . H10 H 0.6631 0.5335 0.5902 0.028 Uiso 1 1 calc R . . C11 C 0.6848(4) 0.3907(2) 0.56784(9) 0.0200(6) Uani 1 1 d . . . C12 C 0.5829(4) 0.3203(2) 0.54323(9) 0.0198(6) Uani 1 1 d . . . H12 H 0.6413 0.2557 0.5396 0.024 Uiso 1 1 calc R . . C13 C 0.3103(4) 0.2649(2) 0.40170(8) 0.0160(5) Uani 1 1 d . . . H13 H 0.1869 0.2992 0.4025 0.019 Uiso 1 1 calc R . . C14 C 0.3983(5) 0.2602(2) 0.36570(9) 0.0191(6) Uani 1 1 d . . . H14 H 0.3356 0.2904 0.3424 0.023 Uiso 1 1 calc R . . C15 C 0.5783(4) 0.2109(2) 0.36420(9) 0.0182(6) Uani 1 1 d . . . H15 H 0.6424 0.2080 0.3400 0.022 Uiso 1 1 calc R . . C16 C 0.6644(4) 0.1655(2) 0.39896(8) 0.0149(5) Uani 1 1 d . . . C17 C 0.5652(4) 0.1730(2) 0.43383(8) 0.0151(5) Uani 1 1 d . . . H17 H 0.6221 0.1415 0.4574 0.018 Uiso 1 1 calc R . . C18 C 0.8495(4) 0.1070(2) 0.40016(9) 0.0170(6) Uani 1 1 d . . . H18 H 0.9026 0.0785 0.4247 0.020 Uiso 1 1 calc R . . C19 C 1.2098(4) 0.0251(2) 0.34503(9) 0.0179(6) Uani 1 1 d . . . H19 H 1.1641 0.0580 0.3209 0.021 Uiso 1 1 calc R . . C20 C 1.7348(4) -0.1452(2) 0.34396(8) 0.0162(5) Uani 1 1 d . . . H20 H 1.8525 -0.1842 0.3430 0.019 Uiso 1 1 calc R . . C21 C 1.6562(4) -0.1307(2) 0.38053(9) 0.0181(6) Uani 1 1 d . . . H21 H 1.7204 -0.1584 0.4042 0.022 Uiso 1 1 calc R . . C22 C 1.4827(4) -0.0754(2) 0.38204(8) 0.0171(6) Uani 1 1 d . . . H22 H 1.4249 -0.0652 0.4067 0.020 Uiso 1 1 calc R . . C23 C 1.3942(4) -0.0347(2) 0.34654(8) 0.0159(5) Uani 1 1 d . . . C24 C 1.4844(4) -0.0508(2) 0.31144(8) 0.0162(5) Uani 1 1 d . . . H24 H 1.4264 -0.0216 0.2875 0.019 Uiso 1 1 calc R . . N1 N 1.6730(4) 0.8318(2) 0.74455(8) 0.0233(6) Uani 1 1 d . . . N2 N 2.1498(4) 0.6350(2) 0.74253(10) 0.0314(7) Uani 1 1 d . . . N3 N 1.6720(4) 0.52218(18) 0.71984(7) 0.0159(5) Uani 1 1 d . . . N4 N 1.1553(4) 0.3989(2) 0.62700(8) 0.0219(5) Uani 1 1 d . . . N5 N 0.9684(4) 0.4319(2) 0.61015(8) 0.0223(5) Uani 1 1 d . . . N6 N 0.4041(4) 0.34045(19) 0.52438(7) 0.0186(5) Uani 1 1 d . . . N7 N 0.2937(4) 0.0351(2) 0.51087(8) 0.0263(6) Uani 1 1 d . . . N8 N -0.0958(5) 0.3120(2) 0.47564(11) 0.0383(8) Uani 1 1 d . . . N9 N 0.3921(3) 0.22309(17) 0.43546(7) 0.0137(4) Uani 1 1 d . . . N10 N 0.9396(4) 0.09438(19) 0.36839(8) 0.0192(5) Uani 1 1 d . . . N11 N 1.1105(4) 0.03319(19) 0.37584(7) 0.0186(5) Uani 1 1 d . . . N12 N 1.6510(3) -0.10606(18) 0.30985(7) 0.0142(5) Uani 1 1 d . . . O1 O 1.5941(3) 0.75230(16) 0.72860(6) 0.0217(4) Uani 1 1 d . . . O2 O 1.8090(3) 0.81199(17) 0.77033(7) 0.0244(5) Uani 1 1 d . . . O3 O 2.0558(3) 0.61273(18) 0.77314(7) 0.0259(5) Uani 1 1 d . . . O4 O 2.0400(4) 0.6643(2) 0.71365(8) 0.0342(6) Uani 1 1 d . . . O5 O 0.3766(3) 0.11675(18) 0.52436(6) 0.0246(5) Uani 1 1 d . . . O6 O 0.1857(4) 0.0481(2) 0.48038(8) 0.0339(6) Uani 1 1 d . . . O7 O -0.0295(4) 0.2380(2) 0.49468(14) 0.0649(11) Uani 1 1 d . . . O8 O 0.0248(4) 0.3617(3) 0.45916(9) 0.0567(9) Uani 1 1 d . . . O9 O 0.9185(5) 0.1328(3) 0.56692(11) 0.0551(8) Uani 1 1 d D . . H9A H 0.914(9) 0.081(3) 0.5855(14) 0.083 Uiso 1 1 d D . . H9B H 0.877(9) 0.113(4) 0.5407(9) 0.083 Uiso 1 1 d D . . Zn1 Zn 1.76772(5) 0.64059(2) 0.756507(9) 0.01388(9) Uani 1 1 d . . . Zn2 Zn 0.26303(5) 0.22950(3) 0.488696(9) 0.01516(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 0.0148(14) 0.0237(15) 0.0211(14) 0.0013(12) -0.0008(11) 0.0012(11) C2 0.0221(15) 0.0186(14) 0.0272(16) -0.0028(12) 0.0049(12) 0.0024(12) C3 0.0228(15) 0.0175(13) 0.0209(14) -0.0045(11) 0.0028(12) -0.0059(11) C4 0.0160(14) 0.0215(14) 0.0146(13) 0.0008(11) 0.0024(11) -0.0026(11) C5 0.0142(13) 0.0190(13) 0.0166(13) -0.0001(11) 0.0020(10) -0.0009(11) C6 0.0181(14) 0.0225(14) 0.0188(14) -0.0008(11) 0.0009(11) -0.0017(11) C7 0.0232(16) 0.0234(15) 0.0234(15) -0.0014(12) -0.0043(12) 0.0004(12) C8 0.0161(14) 0.0256(15) 0.0194(14) 0.0023(12) 0.0023(11) 0.0043(12) C9 0.0240(16) 0.0229(15) 0.0278(16) -0.0020(12) 0.0042(13) 0.0042(12) C10 0.0251(16) 0.0223(15) 0.0217(15) -0.0043(12) 0.0000(12) -0.0021(12) C11 0.0182(14) 0.0235(15) 0.0180(14) -0.0015(11) -0.0015(11) -0.0003(11) C12 0.0172(14) 0.0221(14) 0.0197(14) -0.0017(11) -0.0007(11) 0.0019(11) C13 0.0169(14) 0.0133(12) 0.0175(13) -0.0014(10) -0.0002(11) 0.0026(10) C14 0.0231(15) 0.0194(14) 0.0142(13) 0.0012(11) -0.0016(11) 0.0020(11) C15 0.0227(15) 0.0167(13) 0.0155(13) -0.0002(10) 0.0045(11) 0.0008(11) C16 0.0169(13) 0.0121(12) 0.0158(13) -0.0023(10) 0.0023(10) -0.0014(10) C17 0.0147(13) 0.0157(13) 0.0145(13) -0.0011(10) -0.0014(10) -0.0015(10) C18 0.0171(14) 0.0160(13) 0.0179(13) -0.0014(10) 0.0011(11) 0.0000(11) C19 0.0198(14) 0.0169(13) 0.0170(13) 0.0001(10) 0.0009(11) 0.0027(11) C20 0.0138(13) 0.0163(13) 0.0181(13) 0.0000(10) -0.0012(10) 0.0011(10) C21 0.0203(14) 0.0201(14) 0.0135(13) 0.0011(10) -0.0011(11) -0.0007(11) C22 0.0196(14) 0.0182(13) 0.0135(13) -0.0015(10) 0.0021(11) -0.0011(11) C23 0.0150(13) 0.0143(12) 0.0184(13) -0.0020(10) 0.0023(10) -0.0003(10) C24 0.0144(13) 0.0185(13) 0.0153(13) 0.0017(10) -0.0006(10) 0.0003(10) N1 0.0288(14) 0.0199(12) 0.0216(13) 0.0031(10) 0.0051(11) 0.0008(11) N2 0.0180(14) 0.0356(16) 0.0417(18) -0.0074(13) 0.0098(12) -0.0027(12) N3 0.0142(11) 0.0189(12) 0.0146(11) -0.0002(9) 0.0005(9) -0.0012(9) N4 0.0180(13) 0.0263(13) 0.0209(13) -0.0019(10) -0.0028(10) -0.0020(10) N5 0.0194(13) 0.0272(14) 0.0195(12) -0.0007(10) -0.0038(10) -0.0018(11) N6 0.0154(12) 0.0236(13) 0.0166(12) -0.0005(9) 0.0002(9) 0.0020(10) N7 0.0300(15) 0.0227(13) 0.0280(14) 0.0066(11) 0.0137(12) 0.0052(11) N8 0.0301(17) 0.0313(17) 0.052(2) -0.0146(15) -0.0059(15) -0.0013(13) N9 0.0137(11) 0.0128(11) 0.0144(11) -0.0021(8) 0.0003(9) -0.0013(9) N10 0.0181(12) 0.0183(12) 0.0217(12) -0.0005(10) 0.0044(10) 0.0043(10) N11 0.0186(12) 0.0182(12) 0.0192(12) 0.0010(9) 0.0035(10) 0.0030(10) N12 0.0130(11) 0.0149(11) 0.0149(11) -0.0012(9) 0.0014(9) 0.0006(9) O1 0.0267(12) 0.0219(11) 0.0160(10) -0.0012(8) -0.0014(9) -0.0014(9) O2 0.0221(11) 0.0260(11) 0.0249(11) -0.0029(9) 0.0007(9) -0.0037(9) O3 0.0143(10) 0.0323(12) 0.0315(12) -0.0008(10) 0.0038(9) -0.0002(9) O4 0.0331(14) 0.0398(14) 0.0310(13) -0.0042(11) 0.0111(11) -0.0050(11) O5 0.0258(12) 0.0297(12) 0.0179(11) 0.0030(9) -0.0001(9) 0.0045(9) O6 0.0328(14) 0.0370(14) 0.0317(13) -0.0032(11) 0.0003(11) -0.0124(11) O7 0.0217(14) 0.0350(16) 0.138(4) 0.0185(19) 0.0046(18) 0.0011(12) O8 0.0262(15) 0.109(3) 0.0347(16) 0.0015(17) 0.0036(12) 0.0093(17) O9 0.058(2) 0.0458(19) 0.061(2) 0.0028(16) -0.0015(18) 0.0024(16) Zn1 0.01183(16) 0.01699(16) 0.01279(16) -0.00037(12) 0.00074(11) -0.00120(12) Zn2 0.01172(16) 0.02098(17) 0.01271(16) 0.00042(12) 0.00038(12) 0.00238(12) _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 N3 1.341(4) . ? C1 C2 1.383(4) . ? C1 H1 0.9500 . ? C2 C3 1.376(4) . ? C2 H2 0.9500 . ? C3 C4 1.396(4) . ? C3 H3 0.9500 . ? C4 C5 1.383(4) . ? C4 C6 1.462(4) . ? C5 N3 1.349(4) . ? C5 H5 0.9500 . ? C6 N4 1.279(4) . ? C6 H6 0.9500 . ? C7 N5 1.270(4) . ? C7 C11 1.474(4) . ? C7 H7 0.9500 . ? C8 N6 1.346(4) . ? C8 C9 1.385(4) . ? C8 H8 0.9500 . ? C9 C10 1.382(5) . ? C9 H9 0.9500 . ? C10 C11 1.387(4) . ? C10 H10 0.9500 . ? C11 C12 1.392(4) . ? C12 N6 1.348(4) . ? C12 H12 0.9500 . ? C13 N9 1.342(4) . ? C13 C14 1.387(4) . ? C13 H13 0.9500 . ? C14 C15 1.383(4) . ? C14 H14 0.9500 . ? C15 C16 1.399(4) . ? C15 H15 0.9500 . ? C16 C17 1.394(4) . ? C16 C18 1.468(4) . ? C17 N9 1.348(4) . ? C17 H17 0.9500 . ? C18 N10 1.277(4) . ? C18 H18 0.9500 . ? C19 N11 1.278(4) . ? C19 C23 1.473(4) . ? C19 H19 0.9500 . ? C20 N12 1.342(4) . ? C20 C21 1.386(4) . ? C20 H20 0.9500 . ? C21 C22 1.386(4) . ? C21 H21 0.9500 . ? C22 C23 1.400(4) . ? C22 H22 0.9500 . ? C23 C24 1.383(4) . ? C24 N12 1.345(4) . ? C24 H24 0.9500 . ? N1 O2 1.242(4) . ? N1 O1 1.276(3) . ? N2 O4 1.238(4) . ? N2 O3 1.281(4) . ? N3 Zn1 2.063(2) . ? N4 N5 1.414(4) . ? N6 Zn2 2.078(3) . ? N7 O6 1.224(4) . ? N7 O5 1.282(4) . ? N8 O8 1.211(5) . ? N8 O7 1.233(5) . ? N9 Zn2 2.048(2) . ? N10 N11 1.416(3) . ? N12 Zn1 2.060(2) 4_565 ? O1 Zn1 2.065(2) . ? O2 Zn1 2.321(2) . ? O3 Zn1 2.018(2) . ? O4 Zn1 2.438(2) . ? O5 Zn2 2.024(2) . ? O6 Zn2 2.461(3) . ? O7 Zn2 2.005(3) . ? O9 H9A 0.93(2) . ? O9 H9B 0.94(2) . ? Zn1 N12 2.060(2) 4_566 ? 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 N3 C1 C2 122.5(3) . . ? N3 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C3 C2 C1 119.3(3) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 119.1(3) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 118.0(3) . . ? C5 C4 C6 117.8(3) . . ? C3 C4 C6 124.1(3) . . ? N3 C5 C4 123.1(3) . . ? N3 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? N4 C6 C4 121.8(3) . . ? N4 C6 H6 119.1 . . ? C4 C6 H6 119.1 . . ? N5 C7 C11 118.6(3) . . ? N5 C7 H7 120.7 . . ? C11 C7 H7 120.7 . . ? N6 C8 C9 122.6(3) . . ? N6 C8 H8 118.7 . . ? C9 C8 H8 118.7 . . ? C10 C9 C8 118.6(3) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? C9 C10 C11 119.7(3) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C12 118.5(3) . . ? C10 C11 C7 121.0(3) . . ? C12 C11 C7 120.5(3) . . ? N6 C12 C11 122.2(3) . . ? N6 C12 H12 118.9 . . ? C11 C12 H12 118.9 . . ? N9 C13 C14 122.7(3) . . ? N9 C13 H13 118.6 . . ? C14 C13 H13 118.6 . . ? C15 C14 C13 119.2(3) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C14 C15 C16 118.9(3) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? C17 C16 C15 118.3(3) . . ? C17 C16 C18 118.4(3) . . ? C15 C16 C18 123.3(3) . . ? N9 C17 C16 122.8(3) . . ? N9 C17 H17 118.6 . . ? C16 C17 H17 118.6 . . ? N10 C18 C16 120.3(3) . . ? N10 C18 H18 119.9 . . ? C16 C18 H18 119.9 . . ? N11 C19 C23 120.7(3) . . ? N11 C19 H19 119.7 . . ? C23 C19 H19 119.7 . . ? N12 C20 C21 122.5(3) . . ? N12 C20 H20 118.8 . . ? C21 C20 H20 118.8 . . ? C22 C21 C20 119.1(3) . . ? C22 C21 H21 120.5 . . ? C20 C21 H21 120.5 . . ? C21 C22 C23 118.7(3) . . ? C21 C22 H22 120.7 . . ? C23 C22 H22 120.7 . . ? C24 C23 C22 118.6(3) . . ? C24 C23 C19 118.6(3) . . ? C22 C23 C19 122.8(3) . . ? N12 C24 C23 122.7(3) . . ? N12 C24 H24 118.7 . . ? C23 C24 H24 118.7 . . ? O2 N1 O1 112.5(2) . . ? O4 N2 O3 113.3(3) . . ? C1 N3 C5 117.9(3) . . ? C1 N3 Zn1 121.7(2) . . ? C5 N3 Zn1 120.4(2) . . ? C6 N4 N5 110.2(3) . . ? C7 N5 N4 112.9(3) . . ? C8 N6 C12 118.4(3) . . ? C8 N6 Zn2 122.4(2) . . ? C12 N6 Zn2 119.2(2) . . ? O6 N7 O5 113.2(3) . . ? O8 N8 O7 115.8(3) . . ? C13 N9 C17 118.1(2) . . ? C13 N9 Zn2 123.0(2) . . ? C17 N9 Zn2 118.86(19) . . ? C18 N10 N11 111.1(2) . . ? C19 N11 N10 112.0(2) . . ? C20 N12 C24 118.4(2) . . ? C20 N12 Zn1 119.45(19) . 4_565 ? C24 N12 Zn1 121.98(19) . 4_565 ? N1 O1 Zn1 101.01(17) . . ? N1 O2 Zn1 89.67(17) . . ? N2 O3 Zn1 105.2(2) . . ? N2 O4 Zn1 86.11(19) . . ? N7 O5 Zn2 105.84(18) . . ? N7 O6 Zn2 86.21(18) . . ? N8 O7 Zn2 108.4(3) . . ? H9A O9 H9B 114(5) . . ? O3 Zn1 N12 98.22(9) . 4_566 ? O3 Zn1 N3 106.27(10) . . ? N12 Zn1 N3 103.16(10) 4_566 . ? O3 Zn1 O1 139.39(10) . . ? N12 Zn1 O1 108.10(9) 4_566 . ? N3 Zn1 O1 97.34(9) . . ? O3 Zn1 O2 91.32(9) . . ? N12 Zn1 O2 95.15(9) 4_566 . ? N3 Zn1 O2 152.23(9) . . ? O1 Zn1 O2 56.69(8) . . ? O3 Zn1 O4 55.40(9) . . ? N12 Zn1 O4 153.56(9) 4_566 . ? N3 Zn1 O4 87.83(9) . . ? O1 Zn1 O4 93.95(9) . . ? O2 Zn1 O4 84.72(9) . . ? O7 Zn2 O5 108.36(12) . . ? O7 Zn2 N9 125.23(15) . . ? O5 Zn2 N9 108.56(9) . . ? O7 Zn2 N6 108.45(13) . . ? O5 Zn2 N6 92.27(10) . . ? N9 Zn2 N6 108.98(10) . . ? O7 Zn2 O6 82.13(11) . . ? O5 Zn2 O6 54.57(9) . . ? N9 Zn2 O6 87.80(9) . . ? N6 Zn2 O6 146.62(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C1 C2 C3 -0.8(5) . . . . ? C1 C2 C3 C4 -0.5(5) . . . . ? C2 C3 C4 C5 1.5(4) . . . . ? C2 C3 C4 C6 -176.6(3) . . . . ? C3 C4 C5 N3 -1.4(4) . . . . ? C6 C4 C5 N3 176.9(3) . . . . ? C5 C4 C6 N4 -175.8(3) . . . . ? C3 C4 C6 N4 2.3(5) . . . . ? N6 C8 C9 C10 0.8(5) . . . . ? C8 C9 C10 C11 -0.3(5) . . . . ? C9 C10 C11 C12 -0.5(5) . . . . ? C9 C10 C11 C7 179.1(3) . . . . ? N5 C7 C11 C10 1.7(5) . . . . ? N5 C7 C11 C12 -178.6(3) . . . . ? C10 C11 C12 N6 0.8(5) . . . . ? C7 C11 C12 N6 -178.8(3) . . . . ? N9 C13 C14 C15 -0.3(4) . . . . ? C13 C14 C15 C16 1.3(4) . . . . ? C14 C15 C16 C17 -0.7(4) . . . . ? C14 C15 C16 C18 176.8(3) . . . . ? C15 C16 C17 N9 -0.9(4) . . . . ? C18 C16 C17 N9 -178.5(3) . . . . ? C17 C16 C18 N10 176.6(3) . . . . ? C15 C16 C18 N10 -0.9(4) . . . . ? N12 C20 C21 C22 1.1(4) . . . . ? C20 C21 C22 C23 -0.8(4) . . . . ? C21 C22 C23 C24 -0.5(4) . . . . ? C21 C22 C23 C19 180.0(3) . . . . ? N11 C19 C23 C24 172.8(3) . . . . ? N11 C19 C23 C22 -7.7(4) . . . . ? C22 C23 C24 N12 1.8(4) . . . . ? C19 C23 C24 N12 -178.7(3) . . . . ? C2 C1 N3 C5 1.0(4) . . . . ? C2 C1 N3 Zn1 -177.0(2) . . . . ? C4 C5 N3 C1 0.1(4) . . . . ? C4 C5 N3 Zn1 178.1(2) . . . . ? C4 C6 N4 N5 179.9(3) . . . . ? C11 C7 N5 N4 179.7(3) . . . . ? C6 N4 N5 C7 -179.9(3) . . . . ? C9 C8 N6 C12 -0.6(5) . . . . ? C9 C8 N6 Zn2 178.6(2) . . . . ? C11 C12 N6 C8 -0.3(4) . . . . ? C11 C12 N6 Zn2 -179.4(2) . . . . ? C14 C13 N9 C17 -1.3(4) . . . . ? C14 C13 N9 Zn2 -179.9(2) . . . . ? C16 C17 N9 C13 1.9(4) . . . . ? C16 C17 N9 Zn2 -179.4(2) . . . . ? C16 C18 N10 N11 -178.0(2) . . . . ? C23 C19 N11 N10 179.5(2) . . . . ? C18 N10 N11 C19 -175.7(3) . . . . ? C21 C20 N12 C24 0.0(4) . . . . ? C21 C20 N12 Zn1 -175.5(2) . . . 4_565 ? C23 C24 N12 C20 -1.5(4) . . . . ? C23 C24 N12 Zn1 174.0(2) . . . 4_565 ? O2 N1 O1 Zn1 -2.9(3) . . . . ? O1 N1 O2 Zn1 2.5(2) . . . . ? O4 N2 O3 Zn1 -0.6(3) . . . . ? O3 N2 O4 Zn1 0.5(3) . . . . ? O6 N7 O5 Zn2 4.3(3) . . . . ? O5 N7 O6 Zn2 -3.4(2) . . . . ? O8 N8 O7 Zn2 -1.4(5) . . . . ? N2 O3 Zn1 N12 -177.7(2) . . . 4_566 ? N2 O3 Zn1 N3 75.9(2) . . . . ? N2 O3 Zn1 O1 -47.1(3) . . . . ? N2 O3 Zn1 O2 -82.3(2) . . . . ? N2 O3 Zn1 O4 0.33(18) . . . . ? C1 N3 Zn1 O3 12.1(2) . . . . ? C5 N3 Zn1 O3 -165.9(2) . . . . ? C1 N3 Zn1 N12 -90.7(2) . . . 4_566 ? C5 N3 Zn1 N12 91.3(2) . . . 4_566 ? C1 N3 Zn1 O1 158.7(2) . . . . ? C5 N3 Zn1 O1 -19.3(2) . . . . ? C1 N3 Zn1 O2 139.4(2) . . . . ? C5 N3 Zn1 O2 -38.6(3) . . . . ? C1 N3 Zn1 O4 65.0(2) . . . . ? C5 N3 Zn1 O4 -113.0(2) . . . . ? N1 O1 Zn1 O3 -41.9(2) . . . . ? N1 O1 Zn1 N12 85.86(19) . . . 4_566 ? N1 O1 Zn1 N3 -167.66(18) . . . . ? N1 O1 Zn1 O2 1.70(16) . . . . ? N1 O1 Zn1 O4 -79.35(18) . . . . ? N1 O2 Zn1 O3 151.60(18) . . . . ? N1 O2 Zn1 N12 -110.02(18) . . . 4_566 ? N1 O2 Zn1 N3 21.4(3) . . . . ? N1 O2 Zn1 O1 -1.71(16) . . . . ? N1 O2 Zn1 O4 96.53(18) . . . . ? N2 O4 Zn1 O3 -0.33(18) . . . . ? N2 O4 Zn1 N12 4.0(3) . . . 4_566 ? N2 O4 Zn1 N3 -111.8(2) . . . . ? N2 O4 Zn1 O1 150.95(19) . . . . ? N2 O4 Zn1 O2 94.94(19) . . . . ? N8 O7 Zn2 O5 174.4(3) . . . . ? N8 O7 Zn2 N9 -55.5(3) . . . . ? N8 O7 Zn2 N6 75.5(3) . . . . ? N8 O7 Zn2 O6 -137.1(3) . . . . ? N7 O5 Zn2 O7 63.2(2) . . . . ? N7 O5 Zn2 N9 -75.6(2) . . . . ? N7 O5 Zn2 N6 173.48(19) . . . . ? N7 O5 Zn2 O6 -2.40(17) . . . . ? C13 N9 Zn2 O7 28.9(3) . . . . ? C17 N9 Zn2 O7 -149.7(2) . . . . ? C13 N9 Zn2 O5 159.0(2) . . . . ? C17 N9 Zn2 O5 -19.6(2) . . . . ? C13 N9 Zn2 N6 -101.8(2) . . . . ? C17 N9 Zn2 N6 79.5(2) . . . . ? C13 N9 Zn2 O6 107.7(2) . . . . ? C17 N9 Zn2 O6 -71.0(2) . . . . ? C8 N6 Zn2 O7 -35.6(3) . . . . ? C12 N6 Zn2 O7 143.5(2) . . . . ? C8 N6 Zn2 O5 -145.9(2) . . . . ? C12 N6 Zn2 O5 33.3(2) . . . . ? C8 N6 Zn2 N9 103.6(2) . . . . ? C12 N6 Zn2 N9 -77.3(2) . . . . ? C8 N6 Zn2 O6 -139.8(2) . . . . ? C12 N6 Zn2 O6 39.4(3) . . . . ? N7 O6 Zn2 O7 -116.8(2) . . . . ? N7 O6 Zn2 O5 2.42(17) . . . . ? N7 O6 Zn2 N9 117.15(19) . . . . ? N7 O6 Zn2 N6 -5.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O9 H9A N11 0.93(2) 2.00(2) 2.929(4) 177(6) 3_756 O9 H9B O6 0.94(2) 2.27(5) 2.924(4) 126(5) 3_656 O9 H9B O7 0.94(2) 2.38(6) 2.838(5) 110(4) 1_655 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.592 _refine_diff_density_min -0.932 _refine_diff_density_rms 0.111 # Attachment 'Z_63_06mz241m.cif' data_06mz241m _database_code_depnum_ccdc_archive 'CCDC 629975' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 N4 O4 Zn' _chemical_formula_weight 341.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8528(4) _cell_length_b 7.1459(4) _cell_length_c 14.3017(8) _cell_angle_alpha 100.9910(10) _cell_angle_beta 91.8270(10) _cell_angle_gamma 94.1040(10) _cell_volume 684.99(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7566 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 30.51 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 1.814 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.437 _exptl_absorpt_correction_T_max 0.550 _exptl_absorpt_process_details 'SADABS in SAINT+ (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 7123 _diffrn_reflns_av_R_equivalents 0.0139 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3386 _reflns_number_gt 3305 _reflns_threshold_expression >I>2\s(I) _computing_data_collection 'SMART 5.630 (Bruker, 1997-2002)' _computing_cell_refinement 'SAINT+ 6.45 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.0323P)^2^+0.3124P] 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 3386 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0220 _refine_ls_R_factor_gt 0.0215 _refine_ls_wR_factor_ref 0.0574 _refine_ls_wR_factor_gt 0.0571 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 -0.0038(2) 0.97526(19) 0.80416(10) 0.0204(2) Uani 1 1 d . . . H1 H -0.0769 0.9042 0.7498 0.024 Uiso 1 1 calc R . . C2 C -0.0828(2) 1.13220(19) 0.85742(10) 0.0223(3) Uani 1 1 d . . . H2 H -0.2073 1.1676 0.8391 0.027 Uiso 1 1 calc R . . C3 C 0.0203(2) 1.23762(18) 0.93768(9) 0.0191(2) Uani 1 1 d . . . C4 C 0.2033(2) 1.18034(19) 0.96022(10) 0.0229(3) Uani 1 1 d . . . H4 H 0.2793 1.2489 1.0143 0.027 Uiso 1 1 calc R . . C5 C 0.2733(2) 1.02273(19) 0.90322(10) 0.0210(2) Uani 1 1 d . . . H5 H 0.3987 0.9859 0.9192 0.025 Uiso 1 1 calc R . . C6 C -0.0631(2) 1.40705(18) 0.99828(11) 0.0252(3) Uani 1 1 d . . . H6A H -0.0752 1.3835 1.0639 0.030 Uiso 1 1 calc R . . H6B H -0.1960 1.4205 0.9725 0.030 Uiso 1 1 calc R . . C7 C 0.58135(19) 0.67401(18) 0.60295(9) 0.0185(2) Uani 1 1 d . . . H7 H 0.5581 0.5404 0.6002 0.022 Uiso 1 1 calc R . . C8 C 0.71179(19) 0.73651(19) 0.54150(9) 0.0196(2) Uani 1 1 d . . . H8 H 0.7755 0.6469 0.4974 0.023 Uiso 1 1 calc R . . C9 C 0.74902(18) 0.93206(19) 0.54482(9) 0.0177(2) Uani 1 1 d . . . C10 C 0.65223(18) 1.05646(18) 0.61150(9) 0.0183(2) Uani 1 1 d . . . H10 H 0.6752 1.1908 0.6168 0.022 Uiso 1 1 calc R . . C11 C 0.52211(18) 0.98285(18) 0.67019(9) 0.0172(2) Uani 1 1 d . . . H11 H 0.4560 1.0693 0.7148 0.021 Uiso 1 1 calc R . . C12 C 0.89420(18) 1.0041(2) 0.48070(10) 0.0206(3) Uani 1 1 d . . . H12A H 0.8713 1.1375 0.4765 0.025 Uiso 1 1 calc R . . H12B H 0.8757 0.9249 0.4158 0.025 Uiso 1 1 calc R . . N1 N 0.49498(18) 0.45751(18) 0.82585(9) 0.0260(2) Uani 1 1 d . . . N2 N -0.04393(19) 0.47876(18) 0.67178(10) 0.0271(3) Uani 1 1 d . . . N3 N 0.48594(15) 0.79409(15) 0.66641(8) 0.0155(2) Uani 1 1 d . . . N4 N 0.17197(16) 0.91944(15) 0.82631(8) 0.0167(2) Uani 1 1 d . . . O1 O 0.41677(17) 0.40646(15) 0.74376(8) 0.0292(2) Uani 1 1 d . . . O2 O 0.45878(15) 0.62554(15) 0.86401(7) 0.0258(2) Uani 1 1 d . . . O3 O -0.01846(17) 0.49619(16) 0.75907(8) 0.0317(2) Uani 1 1 d . . . O4 O 0.08903(15) 0.57185(15) 0.63428(7) 0.0238(2) Uani 1 1 d . . . Zn1 Zn 0.281239(19) 0.680931(18) 0.747704(9) 0.01454(6) 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 0.0217(6) 0.0189(6) 0.0191(6) -0.0009(5) -0.0009(5) 0.0038(5) C2 0.0202(6) 0.0203(6) 0.0255(6) 0.0012(5) 0.0020(5) 0.0053(5) C3 0.0235(6) 0.0131(5) 0.0202(6) 0.0015(4) 0.0079(5) 0.0009(4) C4 0.0273(7) 0.0184(6) 0.0202(6) -0.0029(5) -0.0011(5) 0.0012(5) C5 0.0203(6) 0.0190(6) 0.0219(6) -0.0009(5) -0.0018(5) 0.0029(5) C6 0.0285(7) 0.0150(6) 0.0299(7) -0.0027(5) 0.0128(6) 0.0010(5) C7 0.0191(6) 0.0142(5) 0.0212(6) 0.0010(4) 0.0036(5) 0.0006(4) C8 0.0184(6) 0.0206(6) 0.0189(6) 0.0011(5) 0.0042(5) 0.0018(5) C9 0.0126(5) 0.0234(6) 0.0179(6) 0.0070(5) -0.0007(4) 0.0000(4) C10 0.0166(6) 0.0157(5) 0.0227(6) 0.0049(5) -0.0003(5) -0.0002(4) C11 0.0154(5) 0.0154(5) 0.0203(6) 0.0017(4) 0.0012(4) 0.0017(4) C12 0.0144(6) 0.0282(7) 0.0211(6) 0.0105(5) 0.0016(5) 0.0001(5) N1 0.0236(6) 0.0259(6) 0.0319(6) 0.0117(5) 0.0061(5) 0.0071(5) N2 0.0235(6) 0.0193(5) 0.0368(7) 0.0027(5) 0.0002(5) -0.0026(4) N3 0.0140(5) 0.0149(5) 0.0169(5) 0.0016(4) 0.0018(4) 0.0001(4) N4 0.0184(5) 0.0154(5) 0.0157(5) 0.0007(4) 0.0028(4) 0.0020(4) O1 0.0367(6) 0.0178(5) 0.0328(6) 0.0036(4) 0.0034(4) 0.0038(4) O2 0.0269(5) 0.0260(5) 0.0245(5) 0.0032(4) 0.0020(4) 0.0057(4) O3 0.0325(6) 0.0295(6) 0.0346(6) 0.0103(5) 0.0071(5) -0.0016(4) O4 0.0220(5) 0.0244(5) 0.0230(5) 0.0012(4) 0.0009(4) -0.0022(4) Zn1 0.01440(8) 0.01298(8) 0.01569(8) 0.00089(5) 0.00278(5) 0.00156(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N4 1.3426(17) . ? C1 C2 1.3851(18) . ? C1 H1 0.9500 . ? C2 C3 1.3881(19) . ? C2 H2 0.9500 . ? C3 C4 1.393(2) . ? C3 C6 1.5081(17) . ? C4 C5 1.3841(18) . ? C4 H4 0.9500 . ? C5 N4 1.3437(17) . ? C5 H5 0.9500 . ? C6 C6 1.524(3) 2_587 ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N3 1.3449(16) . ? C7 C8 1.3833(18) . ? C7 H7 0.9500 . ? C8 C9 1.3939(18) . ? C8 H8 0.9500 . ? C9 C10 1.3932(18) . ? C9 C12 1.5035(17) . ? C10 C11 1.3876(17) . ? C10 H10 0.9500 . ? C11 N3 1.3443(16) . ? C11 H11 0.9500 . ? C12 C12 1.544(2) 2_776 ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? N1 O1 1.2519(17) . ? N1 O2 1.2659(16) . ? N2 O3 1.2362(18) . ? N2 O4 1.2809(16) . ? N3 Zn1 2.0673(11) . ? N4 Zn1 2.0579(11) . ? O1 Zn1 2.2214(11) . ? O2 Zn1 2.1436(11) . ? O3 Zn1 2.3879(11) . ? O4 Zn1 2.0515(10) . ? 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 N4 C1 C2 122.67(12) . . ? N4 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 119.84(12) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C4 117.43(12) . . ? C2 C3 C6 121.20(13) . . ? C4 C3 C6 121.37(12) . . ? C5 C4 C3 119.46(12) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? N4 C5 C4 122.95(12) . . ? N4 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C3 C6 C6 112.57(14) . 2_587 ? C3 C6 H6A 109.1 . . ? C6 C6 H6A 109.1 2_587 . ? C3 C6 H6B 109.1 . . ? C6 C6 H6B 109.1 2_587 . ? H6A C6 H6B 107.8 . . ? N3 C7 C8 122.90(12) . . ? N3 C7 H7 118.6 . . ? C8 C7 H7 118.6 . . ? C7 C8 C9 119.48(12) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C10 C9 C8 117.59(12) . . ? C10 C9 C12 121.80(12) . . ? C8 C9 C12 120.57(12) . . ? C11 C10 C9 119.58(12) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? N3 C11 C10 122.61(11) . . ? N3 C11 H11 118.7 . . ? C10 C11 H11 118.7 . . ? C9 C12 C12 110.63(13) . 2_776 ? C9 C12 H12A 109.5 . . ? C12 C12 H12A 109.5 2_776 . ? C9 C12 H12B 109.5 . . ? C12 C12 H12B 109.5 2_776 . ? H12A C12 H12B 108.1 . . ? O1 N1 O2 112.22(11) . . ? O3 N2 O4 113.17(12) . . ? C11 N3 C7 117.83(11) . . ? C11 N3 Zn1 123.23(8) . . ? C7 N3 Zn1 118.85(8) . . ? C1 N4 C5 117.63(11) . . ? C1 N4 Zn1 121.58(9) . . ? C5 N4 Zn1 120.77(9) . . ? N1 O1 Zn1 93.64(8) . . ? N1 O2 Zn1 96.95(8) . . ? N2 O3 Zn1 87.94(8) . . ? N2 O4 Zn1 102.85(9) . . ? O4 Zn1 N4 108.57(4) . . ? O4 Zn1 N3 94.55(4) . . ? N4 Zn1 N3 103.33(4) . . ? O4 Zn1 O2 147.39(4) . . ? N4 Zn1 O2 94.48(4) . . ? N3 Zn1 O2 102.40(4) . . ? O4 Zn1 O1 93.84(4) . . ? N4 Zn1 O1 148.94(4) . . ? N3 Zn1 O1 95.79(4) . . ? O2 Zn1 O1 57.19(4) . . ? O4 Zn1 O3 55.88(4) . . ? N4 Zn1 O3 90.49(4) . . ? N3 Zn1 O3 150.28(4) . . ? O2 Zn1 O3 102.59(4) . . ? O1 Zn1 O3 84.48(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C1 C2 C3 -0.5(2) . . . . ? C1 C2 C3 C4 0.9(2) . . . . ? C1 C2 C3 C6 -178.85(13) . . . . ? C2 C3 C4 C5 -0.5(2) . . . . ? C6 C3 C4 C5 179.30(13) . . . . ? C3 C4 C5 N4 -0.5(2) . . . . ? C2 C3 C6 C6 -118.72(18) . . . 2_587 ? C4 C3 C6 C6 61.5(2) . . . 2_587 ? N3 C7 C8 C9 0.5(2) . . . . ? C7 C8 C9 C10 0.45(19) . . . . ? C7 C8 C9 C12 178.33(12) . . . . ? C8 C9 C10 C11 -1.01(18) . . . . ? C12 C9 C10 C11 -178.87(11) . . . . ? C9 C10 C11 N3 0.73(19) . . . . ? C10 C9 C12 C12 100.03(17) . . . 2_776 ? C8 C9 C12 C12 -77.76(18) . . . 2_776 ? C10 C11 N3 C7 0.17(19) . . . . ? C10 C11 N3 Zn1 -176.41(9) . . . . ? C8 C7 N3 C11 -0.77(19) . . . . ? C8 C7 N3 Zn1 175.96(10) . . . . ? C2 C1 N4 C5 -0.4(2) . . . . ? C2 C1 N4 Zn1 178.23(11) . . . . ? C4 C5 N4 C1 0.9(2) . . . . ? C4 C5 N4 Zn1 -177.76(11) . . . . ? O2 N1 O1 Zn1 -0.36(12) . . . . ? O1 N1 O2 Zn1 0.38(12) . . . . ? O4 N2 O3 Zn1 -3.52(11) . . . . ? O3 N2 O4 Zn1 4.20(13) . . . . ? N2 O4 Zn1 N4 -79.90(9) . . . . ? N2 O4 Zn1 N3 174.40(8) . . . . ? N2 O4 Zn1 O2 52.80(12) . . . . ? N2 O4 Zn1 O1 78.27(9) . . . . ? N2 O4 Zn1 O3 -2.41(8) . . . . ? C1 N4 Zn1 O4 3.72(11) . . . . ? C5 N4 Zn1 O4 -177.70(10) . . . . ? C1 N4 Zn1 N3 103.25(11) . . . . ? C5 N4 Zn1 N3 -78.17(11) . . . . ? C1 N4 Zn1 O2 -152.87(11) . . . . ? C5 N4 Zn1 O2 25.72(11) . . . . ? C1 N4 Zn1 O1 -130.29(11) . . . . ? C5 N4 Zn1 O1 48.30(14) . . . . ? C1 N4 Zn1 O3 -50.20(11) . . . . ? C5 N4 Zn1 O3 128.38(11) . . . . ? C11 N3 Zn1 O4 109.42(10) . . . . ? C7 N3 Zn1 O4 -67.12(10) . . . . ? C11 N3 Zn1 N4 -0.89(11) . . . . ? C7 N3 Zn1 N4 -177.43(9) . . . . ? C11 N3 Zn1 O2 -98.61(10) . . . . ? C7 N3 Zn1 O2 84.85(10) . . . . ? C11 N3 Zn1 O1 -156.24(10) . . . . ? C7 N3 Zn1 O1 27.22(10) . . . . ? C11 N3 Zn1 O3 114.75(11) . . . . ? C7 N3 Zn1 O3 -61.79(13) . . . . ? N1 O2 Zn1 O4 30.47(12) . . . . ? N1 O2 Zn1 N4 166.13(8) . . . . ? N1 O2 Zn1 N3 -89.16(8) . . . . ? N1 O2 Zn1 O1 -0.23(8) . . . . ? N1 O2 Zn1 O3 74.62(8) . . . . ? N1 O1 Zn1 O4 -163.76(8) . . . . ? N1 O1 Zn1 N4 -26.86(13) . . . . ? N1 O1 Zn1 N3 101.27(8) . . . . ? N1 O1 Zn1 O2 0.23(8) . . . . ? N1 O1 Zn1 O3 -108.60(9) . . . . ? N2 O3 Zn1 O4 2.44(8) . . . . ? N2 O3 Zn1 N4 114.70(9) . . . . ? N2 O3 Zn1 N3 -3.98(13) . . . . ? N2 O3 Zn1 O2 -150.60(8) . . . . ? N2 O3 Zn1 O1 -96.01(9) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.380 _refine_diff_density_min -0.638 _refine_diff_density_rms 0.063