# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_ValZnFor _database_code_depnum_ccdc_archive 'CCDC 918487' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ValZnFor _chemical_melting_point ? _chemical_formula_moiety 'C12 H15 N2 O4 Zn, 2H2(O)' _chemical_formula_sum 'C12 H19 N2 O6 Zn' _chemical_formula_weight 352.68 _chemical_absolute_configuration syn 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 Hexagonal _symmetry_space_group_name_H-M P61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z+1/6' '-y, x-y, z+1/3' '-x, -y, z+1/2' '-x+y, -x, z+2/3' 'y, -x+y, z+5/6' _cell_length_a 17.7336(11) _cell_length_b 17.7336(11) _cell_length_c 10.3433(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2817.0(5) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max 29.24 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1074 _exptl_absorpt_coefficient_mu 1.329 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.734 _exptl_absorpt_correction_T_max 0.767 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7392 _diffrn_reflns_av_R_equivalents 0.0692 _diffrn_reflns_av_sigmaI/netI 0.0880 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 29.24 _reflns_number_total 3718 _reflns_number_gt 3227 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1228P)^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 -0.05(3) _refine_ls_number_reflns 3718 _refine_ls_number_parameters 182 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.2060 _refine_ls_wR_factor_gt 0.1895 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _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 0.54447(5) 0.47321(4) 1.15580(9) 0.0241(2) Uani 1 1 d . . . O1 O 0.5712(3) 0.4738(3) 0.9619(4) 0.0328(11) Uani 1 1 d . . . O2 O 0.5147(3) 0.4894(3) 1.3521(4) 0.0262(9) Uani 1 1 d . . . N2 N 0.6746(4) 0.5230(4) 1.1960(5) 0.0313(12) Uani 1 1 d . . . O3 O 0.4770(5) 0.3483(4) 1.1748(5) 0.0544(15) Uani 1 1 d . . . C8 C 0.5327(4) 0.4774(4) 0.8611(6) 0.0244(13) Uani 1 1 d . . . C1 C 0.7105(4) 0.5617(5) 1.3044(6) 0.0330(15) Uani 1 1 d . . . H1 H 0.6766 0.5714 1.3632 0.040 Uiso 1 1 calc R . . C5 C 0.7225(5) 0.5058(6) 1.1108(6) 0.045(2) Uani 1 1 d . . . H5 H 0.6966 0.4760 1.0349 0.054 Uiso 1 1 calc R . . N1 N 0.5086(3) 0.5666(3) 1.1341(5) 0.0235(10) Uani 1 1 d . . . C2 C 0.7965(4) 0.5893(4) 1.3373(6) 0.0313(14) Uani 1 1 d . . . H2 H 0.8193 0.6180 1.4151 0.038 Uiso 1 1 calc R . . C7 C 0.5463(4) 0.4332(4) 0.7429(5) 0.0247(12) Uani 1 1 d . . . H7 H 0.5267 0.3725 0.7657 0.030 Uiso 1 1 calc R . . C9 C 0.6427(5) 0.4773(5) 0.7095(6) 0.0332(15) Uani 1 1 d . . . H9 H 0.6737 0.4798 0.7892 0.040 Uiso 1 1 calc R . . C6 C 0.5915(5) 0.6524(4) 1.1205(7) 0.0315(14) Uani 1 1 d . . . H6A H 0.6274 0.6475 1.0538 0.038 Uiso 1 1 calc R . . H6B H 0.6236 0.6665 1.2012 0.038 Uiso 1 1 calc R . . C3 C 0.8483(4) 0.5735(5) 1.2522(6) 0.0346(15) Uani 1 1 d . . . C4 C 0.8090(5) 0.5315(7) 1.1346(7) 0.049(2) Uani 1 1 d . . . H4 H 0.8411 0.5212 1.0733 0.059 Uiso 1 1 calc R . . C11 C 0.6776(5) 0.5698(5) 0.6650(8) 0.0457(18) Uani 1 1 d . . . H11A H 0.6401 0.5713 0.5992 0.069 Uiso 1 1 calc R . . H11B H 0.7351 0.5920 0.6305 0.069 Uiso 1 1 calc R . . H11C H 0.6797 0.6051 0.7368 0.069 Uiso 1 1 calc R . . C10 C 0.6632(6) 0.4260(6) 0.6112(7) 0.049(2) Uani 1 1 d . . . H10A H 0.6491 0.3706 0.6473 0.073 Uiso 1 1 calc R . . H10B H 0.7240 0.4580 0.5900 0.073 Uiso 1 1 calc R . . H10C H 0.6293 0.4172 0.5344 0.073 Uiso 1 1 calc R . . O4 O 0.3898(5) 0.3119(5) 1.0000(9) 0.086(2) Uani 1 1 d . . . C12 C 0.4134(10) 0.2948(7) 1.1024(11) 0.087(4) Uani 1 1 d . . . H12 H 0.3821 0.2373 1.1305 0.104 Uiso 1 1 calc R . . O5 O 0.784(3) 0.968(3) 0.950(4) 0.42(2) Uiso 1 1 d . . . O6 O 0.0232(15) 0.2273(15) 0.089(2) 0.243(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0335(4) 0.0330(4) 0.0164(3) 0.0009(3) 0.0008(3) 0.0245(3) O1 0.045(3) 0.062(3) 0.013(2) -0.0019(18) -0.0049(18) 0.043(3) O2 0.035(2) 0.040(3) 0.016(2) 0.0049(16) 0.0051(15) 0.028(2) N2 0.031(3) 0.051(4) 0.023(3) 0.001(2) 0.002(2) 0.030(3) O3 0.093(4) 0.033(3) 0.038(3) 0.006(2) 0.014(3) 0.031(3) C8 0.029(3) 0.036(3) 0.012(3) 0.002(2) 0.000(2) 0.019(3) C1 0.034(3) 0.058(4) 0.022(3) -0.001(3) 0.004(3) 0.035(3) C5 0.052(5) 0.088(6) 0.019(3) -0.018(3) -0.008(3) 0.053(5) N1 0.031(3) 0.028(3) 0.018(3) 0.0062(18) 0.0007(19) 0.020(2) C2 0.034(3) 0.046(4) 0.021(3) -0.004(3) -0.002(2) 0.025(3) C7 0.032(3) 0.041(3) 0.011(3) 0.001(2) -0.003(2) 0.027(3) C9 0.033(4) 0.048(4) 0.023(3) -0.002(3) -0.001(2) 0.024(3) C6 0.039(4) 0.034(4) 0.029(3) 0.004(2) 0.006(2) 0.024(3) C3 0.037(4) 0.053(4) 0.018(3) 0.006(3) 0.003(2) 0.026(3) C4 0.046(4) 0.104(7) 0.023(3) 0.003(4) 0.009(3) 0.057(5) C11 0.038(4) 0.052(4) 0.042(4) 0.004(4) 0.008(3) 0.018(4) C10 0.049(5) 0.076(6) 0.037(4) -0.002(4) 0.011(3) 0.042(5) O4 0.092(6) 0.081(5) 0.069(5) 0.007(4) 0.001(4) 0.030(5) C12 0.136(11) 0.038(5) 0.061(7) 0.005(5) 0.029(7) 0.024(6) _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 1.931(6) . ? Zn1 N2 2.060(6) . ? Zn1 O1 2.060(4) . ? Zn1 N1 2.063(4) . ? Zn1 O2 2.154(4) . ? O1 C8 1.265(8) . ? O2 C8 1.247(8) 4_665 ? N2 C1 1.302(9) . ? N2 C5 1.359(8) . ? O3 C12 1.290(15) . ? C8 O2 1.247(8) 4_664 ? C8 C7 1.535(8) . ? C1 C2 1.391(9) . ? C5 C4 1.386(11) . ? N1 C7 1.489(7) 4_665 ? N1 C6 1.503(9) . ? C2 C3 1.399(9) . ? C7 N1 1.489(7) 4_664 ? C7 C9 1.522(9) . ? C9 C11 1.508(11) . ? C9 C10 1.524(10) . ? C6 C3 1.521(9) 6_564 ? C3 C4 1.414(11) . ? C3 C6 1.521(9) 2_655 ? O4 C12 1.231(15) . ? 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 N2 113.0(3) . . ? O3 Zn1 O1 96.5(2) . . ? N2 Zn1 O1 89.4(2) . . ? O3 Zn1 N1 132.0(3) . . ? N2 Zn1 N1 114.0(2) . . ? O1 Zn1 N1 93.05(19) . . ? O3 Zn1 O2 90.3(2) . . ? N2 Zn1 O2 92.84(18) . . ? O1 Zn1 O2 171.41(18) . . ? N1 Zn1 O2 78.48(17) . . ? C8 O1 Zn1 132.4(4) . . ? C8 O2 Zn1 113.7(4) 4_665 . ? C1 N2 C5 118.7(6) . . ? C1 N2 Zn1 123.2(4) . . ? C5 N2 Zn1 117.7(5) . . ? C12 O3 Zn1 126.7(7) . . ? O2 C8 O1 126.4(6) 4_664 . ? O2 C8 C7 119.8(5) 4_664 . ? O1 C8 C7 113.8(5) . . ? N2 C1 C2 123.9(6) . . ? N2 C5 C4 121.5(6) . . ? C7 N1 C6 112.3(5) 4_665 . ? C7 N1 Zn1 112.6(4) 4_665 . ? C6 N1 Zn1 106.4(3) . . ? C1 C2 C3 119.3(6) . . ? N1 C7 C9 113.2(5) 4_664 . ? N1 C7 C8 109.3(4) 4_664 . ? C9 C7 C8 110.0(5) . . ? C11 C9 C7 111.9(6) . . ? C11 C9 C10 110.8(6) . . ? C7 C9 C10 112.7(6) . . ? N1 C6 C3 111.5(5) . 6_564 ? C2 C3 C4 116.5(6) . . ? C2 C3 C6 122.8(6) . 2_655 ? C4 C3 C6 120.5(6) . 2_655 ? C5 C4 C3 120.0(6) . . ? O4 C12 O3 126.7(10) . . ? _diffrn_measured_fraction_theta_max 0.881 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.911 _refine_diff_density_min -0.617 _refine_diff_density_rms 0.146 data_ValZnOAc _database_code_depnum_ccdc_archive 'CCDC 918488' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ValZnOAc _chemical_melting_point ? _chemical_formula_moiety 'C13 H18 N2 O4 Zn, 2H2(O)' _chemical_formula_sum 'C13 H22 N2 O6 Zn' _chemical_formula_weight 367.71 _chemical_absolute_configuration syn 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 Hexagonal _symmetry_space_group_name_H-M P61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z+1/6' '-y, x-y, z+1/3' '-x, -y, z+1/2' '-x+y, -x, z+2/3' 'y, -x+y, z+5/6' _cell_length_a 17.4542(6) _cell_length_b 17.4542(6) _cell_length_c 10.3953(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2742.63(16) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max 29.10 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 1.368 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.727 _exptl_absorpt_correction_T_max 0.761 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38' _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6242 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 29.10 _reflns_number_total 2991 _reflns_number_gt 2779 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+4.4024P] 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 0.01(3) _refine_ls_number_reflns 2991 _refine_ls_number_parameters 192 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1505 _refine_ls_wR_factor_gt 0.1480 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.102 _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 0.53338(4) 0.46204(4) 0.11541(8) 0.01850(18) Uani 1 1 d . . . O1 O 0.5339(3) 0.4346(3) 0.3073(4) 0.0261(9) Uani 1 1 d . . . O2 O 0.5140(3) 0.4885(3) -0.0810(4) 0.0189(8) Uani 1 1 d . . . C8 C 0.5249(4) 0.4673(4) 0.4093(6) 0.0181(11) Uani 1 1 d . . . N2 N 0.4853(4) 0.3297(3) 0.0755(5) 0.0245(11) Uani 1 1 d . . . O3 O 0.6603(3) 0.5413(3) 0.0993(5) 0.0330(10) Uani 1 1 d . . . N1 N 0.4353(3) 0.4953(3) 0.1377(4) 0.0187(10) Uani 1 1 d . . . H1 H 0.4466 0.5276 0.2110 0.022 Uiso 1 1 calc R . . C2 C 0.2080(4) 0.4122(4) 0.1044(7) 0.0251(12) Uani 1 1 d . . . H2 H 0.2012 0.3805 0.0293 0.030 Uiso 1 1 calc R . . C7 C 0.4335(4) 0.5496(4) 0.0277(5) 0.0195(11) Uani 1 1 d . . . H7 H 0.3714 0.5291 0.0075 0.023 Uiso 1 1 calc R . . C1 C 0.4413(4) 0.2924(4) -0.0325(6) 0.0282(14) Uani 1 1 d . . . H1A H 0.4298 0.3262 -0.0899 0.034 Uiso 1 1 calc R . . C3 C 0.2768(4) 0.4311(5) 0.1880(6) 0.0306(14) Uani 1 1 d . . . C6 C 0.3500(4) 0.4123(5) 0.1537(7) 0.0289(14) Uani 1 1 d . . . H6A H 0.3555 0.3769 0.2211 0.035 Uiso 1 1 calc R . . H6B H 0.3350 0.3785 0.0744 0.035 Uiso 1 1 calc R . . C4 C 0.2797(4) 0.4725(6) 0.3031(7) 0.044(2) Uani 1 1 d . . . H4 H 0.3222 0.4817 0.3645 0.053 Uiso 1 1 calc R . . C5 C 0.4999(6) 0.2806(5) 0.1597(7) 0.043(2) Uani 1 1 d . . . H5 H 0.5295 0.3063 0.2360 0.051 Uiso 1 1 calc R . . C10 C 0.5733(5) 0.6849(5) 0.0991(8) 0.0412(17) Uani 1 1 d . . . H10A H 0.5766 0.6473 0.1637 0.062 Uiso 1 1 calc R . . H10B H 0.5957 0.7433 0.1335 0.062 Uiso 1 1 calc R . . H10C H 0.6081 0.6875 0.0260 0.062 Uiso 1 1 calc R . . O4 O 0.6957(4) 0.6237(4) 0.2884(10) 0.076(2) Uani 1 1 d . . . C9 C 0.4779(5) 0.6479(4) 0.0583(6) 0.0285(14) Uani 1 1 d . . . H9 H 0.4793 0.6777 -0.0223 0.034 Uiso 1 1 calc R . . C11 C 0.4258(6) 0.6701(5) 0.1542(8) 0.0442(19) Uani 1 1 d . . . H11A H 0.3667 0.6482 0.1226 0.066 Uiso 1 1 calc R . . H11B H 0.4542 0.7331 0.1648 0.066 Uiso 1 1 calc R . . H11C H 0.4235 0.6431 0.2355 0.066 Uiso 1 1 calc R . . C12 C 0.7084(6) 0.6042(8) 0.1662(11) 0.064(3) Uani 1 1 d . . . C13 C 0.7935(8) 0.6744(9) 0.0897(15) 0.090(4) Uiso 1 1 d . . . H13A H 0.8217 0.7293 0.1362 0.134 Uiso 1 1 calc R . . H13B H 0.7763 0.6838 0.0061 0.134 Uiso 1 1 calc R . . H13C H 0.8339 0.6526 0.0806 0.134 Uiso 1 1 calc R . . O5 O 0.7854(10) 0.7706(8) 0.4118(16) 0.174(7) Uani 1 1 d . . . O6 O 0.791(3) 0.811(3) 0.683(4) 0.41(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0299(3) 0.0281(4) 0.0086(3) 0.0004(3) 0.0002(3) 0.0228(3) O1 0.045(2) 0.041(2) 0.008(2) -0.0050(19) -0.0020(18) 0.033(2) O2 0.034(2) 0.0301(19) 0.0055(19) 0.0016(15) 0.0025(16) 0.0255(17) C8 0.023(3) 0.022(3) 0.013(3) -0.002(2) -0.002(2) 0.014(2) N2 0.044(3) 0.029(3) 0.012(2) -0.006(2) -0.003(2) 0.028(2) O3 0.031(2) 0.048(3) 0.021(3) 0.000(2) -0.003(2) 0.021(2) N1 0.030(2) 0.033(2) 0.003(2) 0.0016(19) 0.0022(18) 0.023(2) C2 0.027(3) 0.033(3) 0.016(3) -0.003(3) -0.005(3) 0.015(2) C7 0.034(3) 0.031(3) 0.005(2) 0.000(2) 0.000(2) 0.024(3) C1 0.044(3) 0.039(3) 0.016(3) -0.003(3) -0.005(3) 0.031(3) C3 0.034(3) 0.052(4) 0.013(3) 0.004(3) 0.004(3) 0.027(3) C6 0.035(3) 0.042(4) 0.016(3) 0.004(3) 0.000(3) 0.025(3) C4 0.034(3) 0.100(6) 0.018(3) -0.009(4) -0.008(3) 0.048(4) C5 0.095(6) 0.042(4) 0.016(3) -0.009(3) -0.012(4) 0.052(4) C10 0.059(4) 0.033(3) 0.031(4) -0.010(3) -0.009(4) 0.023(3) O4 0.063(4) 0.064(4) 0.101(7) 0.029(5) 0.031(5) 0.031(3) C9 0.057(4) 0.029(3) 0.013(3) 0.000(2) -0.001(3) 0.032(3) C11 0.080(6) 0.052(4) 0.025(4) -0.010(3) -0.002(4) 0.052(4) C12 0.046(5) 0.094(8) 0.054(6) 0.020(6) 0.013(5) 0.035(5) O5 0.183(13) 0.109(9) 0.164(17) -0.055(10) -0.017(11) 0.024(9) _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 1.945(5) . ? Zn1 O1 2.053(5) . ? Zn1 N2 2.066(5) . ? Zn1 N1 2.077(4) . ? Zn1 O2 2.157(4) . ? O1 C8 1.250(7) . ? O2 C8 1.262(6) 4_664 ? C8 O2 1.262(6) 4_665 ? C8 C7 1.530(8) 4_665 ? N2 C1 1.332(8) . ? N2 C5 1.336(8) . ? O3 C12 1.214(13) . ? N1 C6 1.479(8) . ? N1 C7 1.496(7) . ? N1 H1 0.9100 . ? C2 C3 1.382(9) . ? C2 C1 1.393(8) 2 ? C2 H2 0.9300 . ? C7 C9 1.522(8) . ? C7 C8 1.530(8) 4_664 ? C7 H7 0.9800 . ? C1 C2 1.393(8) 6_554 ? C1 H1A 0.9300 . ? C3 C4 1.386(10) . ? C3 C6 1.511(9) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C4 C5 1.380(9) 2 ? C4 H4 0.9300 . ? C5 C4 1.380(9) 6_554 ? C5 H5 0.9300 . ? C10 C9 1.515(10) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? O4 C12 1.361(14) . ? C9 C11 1.525(9) . ? C9 H9 0.9800 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.588(17) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 O1 96.5(2) . . ? O3 Zn1 N2 117.3(2) . . ? O1 Zn1 N2 88.90(19) . . ? O3 Zn1 N1 128.0(2) . . ? O1 Zn1 N1 93.32(18) . . ? N2 Zn1 N1 113.8(2) . . ? O3 Zn1 O2 90.61(19) . . ? O1 Zn1 O2 171.66(16) . . ? N2 Zn1 O2 91.69(18) . . ? N1 Zn1 O2 78.83(16) . . ? C8 O1 Zn1 134.5(4) . . ? C8 O2 Zn1 113.4(4) 4_664 . ? O1 C8 O2 125.2(6) . 4_665 ? O1 C8 C7 114.5(5) . 4_665 ? O2 C8 C7 120.4(5) 4_665 4_665 ? C1 N2 C5 119.1(5) . . ? C1 N2 Zn1 122.0(4) . . ? C5 N2 Zn1 119.0(4) . . ? C12 O3 Zn1 128.3(6) . . ? C6 N1 C7 112.2(5) . . ? C6 N1 Zn1 107.8(3) . . ? C7 N1 Zn1 111.9(3) . . ? C6 N1 H1 108.3 . . ? C7 N1 H1 108.3 . . ? Zn1 N1 H1 108.3 . . ? C3 C2 C1 119.1(6) . 2 ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 2 . ? N1 C7 C9 113.3(5) . . ? N1 C7 C8 109.3(4) . 4_664 ? C9 C7 C8 111.2(5) . 4_664 ? N1 C7 H7 107.6 . . ? C9 C7 H7 107.6 . . ? C8 C7 H7 107.6 4_664 . ? N2 C1 C2 122.1(6) . 6_554 ? N2 C1 H1A 119.0 . . ? C2 C1 H1A 119.0 6_554 . ? C2 C3 C4 117.9(6) . . ? C2 C3 C6 121.8(6) . . ? C4 C3 C6 120.2(6) . . ? N1 C6 C3 111.1(5) . . ? N1 C6 H6A 109.4 . . ? C3 C6 H6A 109.4 . . ? N1 C6 H6B 109.4 . . ? C3 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C5 C4 C3 119.8(6) 2 . ? C5 C4 H4 120.1 2 . ? C3 C4 H4 120.1 . . ? N2 C5 C4 121.8(7) . 6_554 ? N2 C5 H5 119.1 . . ? C4 C5 H5 119.1 6_554 . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C10 C9 C7 111.7(5) . . ? C10 C9 C11 112.2(6) . . ? C7 C9 C11 113.0(6) . . ? C10 C9 H9 106.5 . . ? C7 C9 H9 106.5 . . ? C11 C9 H9 106.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O3 C12 O4 129.5(9) . . ? O3 C12 C13 111.6(10) . . ? O4 C12 C13 118.8(11) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 O3 Zn1 O1 C8 92.3(6) . . . . ? N2 Zn1 O1 C8 -150.4(6) . . . . ? N1 Zn1 O1 C8 -36.6(6) . . . . ? O2 Zn1 O1 C8 -56.2(14) . . . . ? O3 Zn1 O2 C8 -110.6(4) . . . 4_664 ? O1 Zn1 O2 C8 38.0(13) . . . 4_664 ? N2 Zn1 O2 C8 132.0(4) . . . 4_664 ? N1 Zn1 O2 C8 18.1(4) . . . 4_664 ? Zn1 O1 C8 O2 23.2(10) . . . 4_665 ? Zn1 O1 C8 C7 -156.3(4) . . . 4_665 ? O3 Zn1 N2 C1 -105.7(5) . . . . ? O1 Zn1 N2 C1 157.5(5) . . . . ? N1 Zn1 N2 C1 64.4(5) . . . . ? O2 Zn1 N2 C1 -14.2(5) . . . . ? O3 Zn1 N2 C5 73.2(6) . . . . ? O1 Zn1 N2 C5 -23.6(6) . . . . ? N1 Zn1 N2 C5 -116.7(6) . . . . ? O2 Zn1 N2 C5 164.7(6) . . . . ? O1 Zn1 O3 C12 -50.3(8) . . . . ? N2 Zn1 O3 C12 -142.4(8) . . . . ? N1 Zn1 O3 C12 49.1(9) . . . . ? O2 Zn1 O3 C12 125.3(8) . . . . ? O3 Zn1 N1 C6 -176.5(4) . . . . ? O1 Zn1 N1 C6 -75.6(4) . . . . ? N2 Zn1 N1 C6 14.6(4) . . . . ? O2 Zn1 N1 C6 101.5(4) . . . . ? O3 Zn1 N1 C7 59.6(5) . . . . ? O1 Zn1 N1 C7 160.5(4) . . . . ? N2 Zn1 N1 C7 -109.2(4) . . . . ? O2 Zn1 N1 C7 -22.3(4) . . . . ? C6 N1 C7 C9 137.5(5) . . . . ? Zn1 N1 C7 C9 -101.2(5) . . . . ? C6 N1 C7 C8 -97.9(5) . . . 4_664 ? Zn1 N1 C7 C8 23.5(6) . . . 4_664 ? C5 N2 C1 C2 -1.8(10) . . . 6_554 ? Zn1 N2 C1 C2 177.1(5) . . . 6_554 ? C1 C2 C3 C4 4.9(11) 2 . . . ? C1 C2 C3 C6 -171.8(6) 2 . . . ? C7 N1 C6 C3 -63.8(6) . . . . ? Zn1 N1 C6 C3 172.5(4) . . . . ? C2 C3 C6 N1 112.4(7) . . . . ? C4 C3 C6 N1 -64.2(9) . . . . ? C2 C3 C4 C5 -5.3(12) . . . 2 ? C6 C3 C4 C5 171.5(7) . . . 2 ? C1 N2 C5 C4 1.4(12) . . . 6_554 ? Zn1 N2 C5 C4 -177.5(6) . . . 6_554 ? N1 C7 C9 C10 57.6(7) . . . . ? C8 C7 C9 C10 -66.0(7) 4_664 . . . ? N1 C7 C9 C11 -70.0(7) . . . . ? C8 C7 C9 C11 166.4(5) 4_664 . . . ? Zn1 O3 C12 O4 20.6(16) . . . . ? Zn1 O3 C12 C13 -154.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.880 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.182 _refine_diff_density_min -0.559 _refine_diff_density_rms 0.111 data_AlaZnCl _database_code_depnum_ccdc_archive 'CCDC 918489' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common AlaZnCl _chemical_melting_point ? _chemical_formula_moiety 'C9 H15 Cl N2 O2 Zn, 2H2(O)' _chemical_formula_sum 'C9 H15 Cl N2 O4 Zn' _chemical_formula_weight 316.07 _chemical_absolute_configuration syn 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' Cl Cl 0.1484 0.1585 '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 Hexagonal _symmetry_space_group_name_H-M P61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z+1/6' '-y, x-y, z+1/3' '-x, -y, z+1/2' '-x+y, -x, z+2/3' 'y, -x+y, z+5/6' _cell_length_a 17.4587(2) _cell_length_b 17.4587(2) _cell_length_c 10.24475(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2704.31(6) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max 29.14 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.150 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 948.0 _exptl_absorpt_coefficient_mu 1.513 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.702 _exptl_absorpt_correction_T_max 0.860 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38' _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19898 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 29.14 _reflns_number_total 4382 _reflns_number_gt 4251 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; OMIT -1 4 0 OMIT 0 7 0 OMIT -1 7 0 OMIT -1 5 0 OMIT -2 3 0 OMIT 0 6 0 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^)+(0.0774P)^2^+1.9858P] 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 0.003(16) _refine_ls_number_reflns 4382 _refine_ls_number_parameters 155 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1253 _refine_ls_wR_factor_gt 0.1237 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.142 _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 0.54190(3) 0.07503(2) 0.15431(4) 0.01997(12) Uani 1 1 d . . . Cl1 Cl 0.68751(7) 0.12589(8) 0.17027(15) 0.0515(3) Uani 1 1 d . . . N1 N 0.45120(19) -0.05763(18) 0.1229(3) 0.0210(6) Uani 1 1 d . . . H1 H 0.4645 -0.0741 0.0458 0.025 Uiso 1 1 calc R . . O1 O 0.50886(17) 0.02240(14) 0.3512(2) 0.0231(5) Uani 1 1 d . . . N2 N 0.5031(2) 0.16469(18) 0.1989(3) 0.0251(6) Uani 1 1 d . . . C9 C 0.5349(4) -0.1280(3) 0.1978(4) 0.0406(10) Uani 1 1 d . . . H9A H 0.5214 -0.1634 0.1203 0.061 Uiso 1 1 calc R . . H9B H 0.5422 -0.1590 0.2699 0.061 Uiso 1 1 calc R . . H9C H 0.5887 -0.0729 0.1847 0.061 Uiso 1 1 calc R . . C7 C 0.4595(3) -0.1101(2) 0.2270(3) 0.0242(7) Uani 1 1 d . . . H7 H 0.4041 -0.1666 0.2340 0.029 Uiso 1 1 calc R . . C4 C 0.4210(3) 0.2147(3) 0.3237(4) 0.0330(8) Uani 1 1 d . . . H4 H 0.3810 0.2043 0.3906 0.040 Uiso 1 1 calc R . . C5 C 0.4469(3) 0.1538(2) 0.2965(4) 0.0300(8) Uani 1 1 d . . . H5 H 0.4247 0.1031 0.3475 0.036 Uiso 1 1 calc R . . C8 C 0.4770(2) -0.0601(2) 0.3558(3) 0.0205(6) Uani 1 1 d . . . C3 C 0.4552(3) 0.2920(3) 0.2504(4) 0.0285(8) Uani 1 1 d . . . C2 C 0.5148(3) 0.3039(2) 0.1496(4) 0.0380(9) Uani 1 1 d . . . H2 H 0.5394 0.3548 0.0987 0.046 Uiso 1 1 calc R . . C1 C 0.5361(3) 0.2391(2) 0.1276(4) 0.0358(9) Uani 1 1 d . . . H1A H 0.5751 0.2471 0.0602 0.043 Uiso 1 1 calc R . . O2 O 0.4608(2) -0.10549(17) 0.4580(2) 0.0324(7) Uani 1 1 d . . . C6 C 0.3624(2) -0.0685(2) 0.1122(4) 0.0274(7) Uani 1 1 d . . . H6A H 0.3624 -0.0306 0.0429 0.033 Uiso 1 1 calc R . . H6B H 0.3480 -0.0497 0.1931 0.033 Uiso 1 1 calc R . . O3 O 0.2801(5) -0.0526(4) 0.4105(5) 0.0990(19) Uani 1 1 d . . . O4 O 0.2495(19) 0.060(2) 0.022(2) 0.444(17) 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 0.0320(2) 0.01100(15) 0.01075(17) -0.00069(12) 0.00078(14) 0.00613(14) Cl1 0.0341(5) 0.0448(6) 0.0557(7) -0.0101(5) 0.0030(5) 0.0048(4) N1 0.0306(14) 0.0135(11) 0.0082(14) -0.0002(9) -0.0021(10) 0.0029(10) O1 0.0423(13) 0.0128(10) 0.0109(11) -0.0015(8) -0.0040(9) 0.0113(9) N2 0.0466(17) 0.0145(12) 0.0139(13) 0.0006(9) 0.0036(11) 0.0150(12) C9 0.072(3) 0.039(2) 0.027(2) -0.0037(16) -0.0039(19) 0.040(2) C7 0.0434(19) 0.0141(13) 0.0093(14) -0.0001(11) -0.0026(13) 0.0100(13) C4 0.042(2) 0.0344(17) 0.0264(19) 0.0067(16) 0.0103(17) 0.0217(16) C5 0.047(2) 0.0211(15) 0.0224(19) 0.0045(12) 0.0063(15) 0.0178(15) C8 0.0368(17) 0.0136(13) 0.0085(15) 0.0010(11) -0.0022(12) 0.0106(12) C3 0.049(2) 0.0291(17) 0.0166(16) -0.0039(13) -0.0066(14) 0.0263(16) C2 0.078(3) 0.0279(16) 0.0179(17) 0.0042(15) 0.0055(19) 0.0335(19) C1 0.069(3) 0.0235(16) 0.0209(19) 0.0045(13) 0.0151(17) 0.0283(18) O2 0.0697(19) 0.0171(11) 0.0077(12) 0.0017(8) -0.0045(10) 0.0196(12) C6 0.0287(17) 0.0221(15) 0.0228(17) 0.0017(12) -0.0013(13) 0.0063(13) O3 0.139(5) 0.097(4) 0.054(3) 0.015(3) 0.002(3) 0.054(4) O4 0.45(3) 0.82(5) 0.249(19) -0.11(3) -0.18(2) 0.47(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N2 2.044(3) . ? Zn1 N1 2.075(3) . ? Zn1 O2 2.087(3) 4_654 ? Zn1 O1 2.171(2) . ? Zn1 Cl1 2.2407(12) . ? N1 C7 1.460(4) . ? N1 C6 1.469(5) . ? N1 H1 0.9100 . ? O1 C8 1.259(4) . ? N2 C1 1.343(4) . ? N2 C5 1.346(5) . ? C9 C7 1.527(6) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C7 C8 1.527(4) . ? C7 H7 0.9800 . ? C4 C5 1.377(5) . ? C4 C3 1.391(5) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C8 O2 1.257(4) . ? C3 C2 1.405(6) . ? C3 C6 1.516(5) 2 ? C2 C1 1.376(5) . ? C2 H2 0.9300 . ? C1 H1A 0.9300 . ? O2 Zn1 2.087(3) 4_655 ? C6 C3 1.516(5) 6_554 ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Zn1 N1 121.97(13) . . ? N2 Zn1 O2 87.84(11) . 4_654 ? N1 Zn1 O2 91.90(11) . 4_654 ? N2 Zn1 O1 89.81(10) . . ? N1 Zn1 O1 77.22(10) . . ? O2 Zn1 O1 165.47(11) 4_654 . ? N2 Zn1 Cl1 115.13(10) . . ? N1 Zn1 Cl1 122.34(10) . . ? O2 Zn1 Cl1 97.75(10) 4_654 . ? O1 Zn1 Cl1 96.23(8) . . ? C7 N1 C6 113.8(3) . . ? C7 N1 Zn1 109.1(2) . . ? C6 N1 Zn1 108.8(2) . . ? C7 N1 H1 108.3 . . ? C6 N1 H1 108.3 . . ? Zn1 N1 H1 108.3 . . ? C8 O1 Zn1 113.0(2) . . ? C1 N2 C5 118.0(3) . . ? C1 N2 Zn1 118.2(3) . . ? C5 N2 Zn1 123.7(2) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C7 C8 109.0(3) . . ? N1 C7 C9 110.6(3) . . ? C8 C7 C9 109.9(3) . . ? N1 C7 H7 109.1 . . ? C8 C7 H7 109.1 . . ? C9 C7 H7 109.1 . . ? C5 C4 C3 119.5(4) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? N2 C5 C4 122.7(3) . . ? N2 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? O2 C8 O1 125.8(3) . . ? O2 C8 C7 116.2(3) . . ? O1 C8 C7 118.0(3) . . ? C4 C3 C2 117.9(3) . . ? C4 C3 C6 121.6(4) . 2 ? C2 C3 C6 120.5(3) . 2 ? C1 C2 C3 118.9(3) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? N2 C1 C2 123.0(4) . . ? N2 C1 H1A 118.5 . . ? C2 C1 H1A 118.5 . . ? C8 O2 Zn1 132.0(2) . 4_655 ? N1 C6 C3 112.5(3) . 6_554 ? N1 C6 H6A 109.1 . . ? C3 C6 H6A 109.1 6_554 . ? N1 C6 H6B 109.1 . . ? C3 C6 H6B 109.1 6_554 . ? H6A C6 H6B 107.8 . . ? 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 N2 Zn1 N1 C7 -113.4(2) . . . . ? O2 Zn1 N1 C7 157.9(2) 4_654 . . . ? O1 Zn1 N1 C7 -31.8(2) . . . . ? Cl1 Zn1 N1 C7 57.5(3) . . . . ? N2 Zn1 N1 C6 11.3(3) . . . . ? O2 Zn1 N1 C6 -77.4(2) 4_654 . . . ? O1 Zn1 N1 C6 92.9(2) . . . . ? Cl1 Zn1 N1 C6 -177.79(19) . . . . ? N2 Zn1 O1 C8 143.8(3) . . . . ? N1 Zn1 O1 C8 20.9(3) . . . . ? O2 Zn1 O1 C8 63.2(5) 4_654 . . . ? Cl1 Zn1 O1 C8 -100.9(2) . . . . ? N1 Zn1 N2 C1 -128.3(3) . . . . ? O2 Zn1 N2 C1 -37.4(3) 4_654 . . . ? O1 Zn1 N2 C1 157.0(3) . . . . ? Cl1 Zn1 N2 C1 60.2(3) . . . . ? N1 Zn1 N2 C5 52.2(4) . . . . ? O2 Zn1 N2 C5 143.1(3) 4_654 . . . ? O1 Zn1 N2 C5 -22.5(3) . . . . ? Cl1 Zn1 N2 C5 -119.3(3) . . . . ? C6 N1 C7 C8 -83.6(4) . . . . ? Zn1 N1 C7 C8 38.2(3) . . . . ? C6 N1 C7 C9 155.5(3) . . . . ? Zn1 N1 C7 C9 -82.8(3) . . . . ? C1 N2 C5 C4 1.3(6) . . . . ? Zn1 N2 C5 C4 -179.2(3) . . . . ? C3 C4 C5 N2 -1.5(7) . . . . ? Zn1 O1 C8 O2 172.4(3) . . . . ? Zn1 O1 C8 C7 -5.0(4) . . . . ? N1 C7 C8 O2 160.3(3) . . . . ? C9 C7 C8 O2 -78.4(4) . . . . ? N1 C7 C8 O1 -22.1(5) . . . . ? C9 C7 C8 O1 99.3(4) . . . . ? C5 C4 C3 C2 0.6(6) . . . . ? C5 C4 C3 C6 -178.2(4) . . . 2 ? C4 C3 C2 C1 0.4(6) . . . . ? C6 C3 C2 C1 179.3(4) 2 . . . ? C5 N2 C1 C2 -0.2(7) . . . . ? Zn1 N2 C1 C2 -179.7(4) . . . . ? C3 C2 C1 N2 -0.7(7) . . . . ? O1 C8 O2 Zn1 10.9(6) . . . 4_655 ? C7 C8 O2 Zn1 -171.6(3) . . . 4_655 ? C7 N1 C6 C3 -60.3(4) . . . 6_554 ? Zn1 N1 C6 C3 177.8(2) . . . 6_554 ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.369 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.110 data_AlaZnFor293K _database_code_depnum_ccdc_archive 'CCDC 918500' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common AlaZnFor293K _chemical_melting_point ? _chemical_formula_moiety 'C10 H12 N2 O4 Zn' _chemical_formula_sum 'C10 H12 N2 O4 Zn' _chemical_formula_weight 289.61 _chemical_absolute_configuration syn 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 Hexagonal _symmetry_space_group_name_H-M P61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z+1/6' '-y, x-y, z+1/3' '-x, -y, z+1/2' '-x+y, -x, z+2/3' 'y, -x+y, z+5/6' _cell_length_a 17.686(2) _cell_length_b 17.686(2) _cell_length_c 10.1964(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2762.2(6) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max 29.510 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.045 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 1.336 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.733 _exptl_absorpt_correction_T_max 0.766 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7796 _diffrn_reflns_av_R_equivalents 0.0922 _diffrn_reflns_av_sigmaI/netI 0.1495 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 29.51 _reflns_number_total 3521 _reflns_number_gt 2118 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1495P)^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 -0.04(5) _refine_ls_number_reflns 3521 _refine_ls_number_parameters 155 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1188 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.2546 _refine_ls_wR_factor_gt 0.1656 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 C1 C 0.7050(7) 0.1534(7) 0.8533(12) 0.053(3) Uani 1 1 d . . . H1A H 0.6720 0.1080 0.7954 0.063 Uiso 1 1 calc R . . C2 C 0.7912(8) 0.2130(8) 0.8194(12) 0.059(3) Uani 1 1 d . . . H2 H 0.8147 0.2066 0.7414 0.070 Uiso 1 1 calc R . . C3 C 0.8413(7) 0.2817(7) 0.9031(10) 0.049(3) Uani 1 1 d . . . C4 C 0.8046(8) 0.2846(7) 1.0177(11) 0.069(4) Uani 1 1 d . . . H4 H 0.8373 0.3282 1.0783 0.083 Uiso 1 1 calc R . . C5 C 0.7178(9) 0.2226(8) 1.0463(10) 0.073(5) Uani 1 1 d . . . H5 H 0.6936 0.2260 1.1255 0.088 Uiso 1 1 calc R . . C6 C 0.9351(7) 0.3508(7) 0.8667(12) 0.053(3) Uani 1 1 d . . . H6A H 0.9757 0.3483 0.9283 0.063 Uiso 1 1 calc R . . H6B H 0.9489 0.3390 0.7796 0.063 Uiso 1 1 calc R . . C7 C 0.4423(7) -0.1099(7) 0.9343(10) 0.043(3) Uani 1 1 d . . . H7 H 0.4504 -0.1593 0.9125 0.051 Uiso 1 1 calc R . . C8 C 0.4564(6) -0.0549(6) 0.8101(10) 0.038(2) Uani 1 1 d . . . C9 C 0.3492(9) -0.1446(10) 0.9840(11) 0.086(5) Uani 1 1 d . . . H9A H 0.3353 -0.1897 1.0476 0.129 Uiso 1 1 calc R . . H9B H 0.3091 -0.1680 0.9118 0.129 Uiso 1 1 calc R . . H9C H 0.3445 -0.0979 1.0238 0.129 Uiso 1 1 calc R . . C10 C 0.4153(17) 0.1077(14) 1.083(2) 0.106(6) Uani 1 1 d . . . H10 H 0.3839 0.1370 1.0834 0.127 Uiso 1 1 calc R . . N1 N 0.5062(6) -0.0560(5) 1.0367(8) 0.0343(18) Uani 1 1 d . . . H1 H 0.4804 -0.0744 1.1165 0.041 Uiso 1 1 calc R . . N2 N 0.6685(6) 0.1578(6) 0.9607(8) 0.048(2) Uani 1 1 d . . . O1 O 0.5029(5) 0.0263(4) 0.8166(7) 0.0452(18) Uani 1 1 d . . . O2 O 0.5799(6) 0.0983(5) 1.2107(7) 0.055(2) Uani 1 1 d . . . O3 O 0.4778(9) 0.1394(7) 1.0100(11) 0.082(3) Uani 1 1 d . . . O4 O 0.3853(10) 0.0431(12) 1.157(2) 0.147(6) Uani 1 1 d . . . Zn1 Zn 0.54117(8) 0.07448(6) 1.01379(12) 0.0369(4) 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 0.055(6) 0.044(6) 0.039(5) -0.014(5) -0.006(6) 0.009(5) C2 0.058(7) 0.050(7) 0.049(7) -0.005(5) 0.010(5) 0.013(6) C3 0.042(6) 0.040(6) 0.047(6) -0.005(4) 0.005(4) 0.008(5) C4 0.070(8) 0.056(7) 0.020(5) -0.010(5) -0.001(5) -0.015(6) C5 0.083(10) 0.055(7) 0.030(6) -0.010(5) 0.022(5) -0.004(7) C6 0.037(6) 0.043(6) 0.052(7) 0.004(5) 0.001(5) 0.001(5) C7 0.055(7) 0.024(5) 0.033(5) 0.001(4) -0.006(4) 0.007(5) C8 0.039(6) 0.029(5) 0.033(5) -0.001(4) -0.002(4) 0.007(5) C9 0.060(9) 0.104(12) 0.025(6) 0.018(6) -0.003(5) -0.011(8) C10 0.15(2) 0.083(14) 0.128(17) 0.001(12) 0.000(15) 0.087(15) N1 0.046(5) 0.027(4) 0.027(4) 0.003(3) 0.001(3) 0.016(3) N2 0.042(5) 0.033(5) 0.042(5) -0.004(4) 0.003(4) -0.001(4) O1 0.054(4) 0.021(4) 0.042(4) 0.001(3) -0.008(3) 0.006(3) O2 0.064(5) 0.040(4) 0.022(4) -0.004(3) -0.002(3) -0.003(4) O3 0.123(9) 0.088(7) 0.066(6) -0.015(6) -0.014(6) 0.076(7) O4 0.108(11) 0.114(12) 0.225(19) 0.031(13) 0.015(12) 0.060(10) Zn1 0.0502(8) 0.0222(5) 0.0274(5) 0.0007(4) 0.0001(5) 0.0100(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 N2 1.294(15) . ? C1 C2 1.395(16) . ? C1 H1A 0.9300 . ? C2 C3 1.383(15) . ? C2 H2 0.9300 . ? C3 C4 1.350(16) . ? C3 C6 1.536(15) . ? C4 C5 1.400(17) . ? C4 H4 0.9300 . ? C5 N2 1.356(14) . ? C5 H5 0.9300 . ? C6 N1 1.468(15) 6_664 ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N1 1.483(12) . ? C7 C9 1.528(18) . ? C7 C8 1.539(14) . ? C7 H7 0.9800 . ? C8 O2 1.239(12) 4_654 ? C8 O1 1.251(11) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 O3 1.21(2) . ? C10 O4 1.25(2) . ? C10 H10 0.9300 . ? N1 C6 1.468(15) 2_545 ? N1 Zn1 2.082(7) . ? N1 H1 0.9100 . ? N2 Zn1 2.054(8) . ? O1 Zn1 2.157(7) . ? O2 C8 1.239(12) 4_655 ? O2 Zn1 2.095(7) . ? O3 Zn1 1.965(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 N2 C1 C2 123.6(10) . . ? N2 C1 H1A 118.2 . . ? C2 C1 H1A 118.2 . . ? C3 C2 C1 119.2(11) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C4 C3 C2 117.3(10) . . ? C4 C3 C6 121.8(9) . . ? C2 C3 C6 120.8(10) . . ? C3 C4 C5 120.6(9) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? N2 C5 C4 121.2(10) . . ? N2 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? N1 C6 C3 109.6(9) 6_664 . ? N1 C6 H6A 109.8 6_664 . ? C3 C6 H6A 109.8 . . ? N1 C6 H6B 109.8 6_664 . ? C3 C6 H6B 109.8 . . ? H6A C6 H6B 108.2 . . ? N1 C7 C9 110.3(10) . . ? N1 C7 C8 110.0(8) . . ? C9 C7 C8 109.2(9) . . ? N1 C7 H7 109.1 . . ? C9 C7 H7 109.1 . . ? C8 C7 H7 109.1 . . ? O2 C8 O1 126.4(10) 4_654 . ? O2 C8 C7 114.3(8) 4_654 . ? O1 C8 C7 119.2(9) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O3 C10 O4 132.0(19) . . ? O3 C10 H10 114.0 . . ? O4 C10 H10 114.0 . . ? C6 N1 C7 111.8(8) 2_545 . ? C6 N1 Zn1 110.0(6) 2_545 . ? C7 N1 Zn1 110.0(6) . . ? C6 N1 H1 108.3 2_545 . ? C7 N1 H1 108.3 . . ? Zn1 N1 H1 108.3 . . ? C1 N2 C5 117.8(9) . . ? C1 N2 Zn1 125.6(7) . . ? C5 N2 Zn1 116.6(7) . . ? C8 O1 Zn1 113.5(6) . . ? C8 O2 Zn1 130.1(7) 4_655 . ? C10 O3 Zn1 111.9(11) . . ? O3 Zn1 N2 108.5(5) . . ? O3 Zn1 N1 135.2(5) . . ? N2 Zn1 N1 115.8(4) . . ? O3 Zn1 O2 97.2(4) . . ? N2 Zn1 O2 88.7(3) . . ? N1 Zn1 O2 90.1(3) . . ? O3 Zn1 O1 93.1(4) . . ? N2 Zn1 O1 93.0(3) . . ? N1 Zn1 O1 78.8(3) . . ? O2 Zn1 O1 168.4(3) . . ? 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 N2 C1 C2 C3 -1(2) . . . . ? C1 C2 C3 C4 3(2) . . . . ? C1 C2 C3 C6 -177.5(12) . . . . ? C2 C3 C4 C5 -3(2) . . . . ? C6 C3 C4 C5 177.6(13) . . . . ? C3 C4 C5 N2 1(2) . . . . ? C4 C3 C6 N1 -57.1(15) . . . 6_664 ? C2 C3 C6 N1 123.7(12) . . . 6_664 ? N1 C7 C8 O2 164.5(10) . . . 4_654 ? C9 C7 C8 O2 -74.3(14) . . . 4_654 ? N1 C7 C8 O1 -14.2(15) . . . . ? C9 C7 C8 O1 107.1(12) . . . . ? C9 C7 N1 C6 145.7(10) . . . 2_545 ? C8 C7 N1 C6 -93.8(10) . . . 2_545 ? C9 C7 N1 Zn1 -91.7(10) . . . . ? C8 C7 N1 Zn1 28.8(11) . . . . ? C2 C1 N2 C5 -2(2) . . . . ? C2 C1 N2 Zn1 178.1(10) . . . . ? C4 C5 N2 C1 2(2) . . . . ? C4 C5 N2 Zn1 -177.9(12) . . . . ? O2 C8 O1 Zn1 173.8(10) 4_654 . . . ? C7 C8 O1 Zn1 -7.7(13) . . . . ? O4 C10 O3 Zn1 0(3) . . . . ? C10 O3 Zn1 N2 -154.6(14) . . . . ? C10 O3 Zn1 N1 33.9(16) . . . . ? C10 O3 Zn1 O2 -63.5(14) . . . . ? C10 O3 Zn1 O1 111.2(14) . . . . ? C1 N2 Zn1 O3 -111.4(11) . . . . ? C5 N2 Zn1 O3 68.5(11) . . . . ? C1 N2 Zn1 N1 62.0(11) . . . . ? C5 N2 Zn1 N1 -118.1(10) . . . . ? C1 N2 Zn1 O2 151.4(11) . . . . ? C5 N2 Zn1 O2 -28.6(10) . . . . ? C1 N2 Zn1 O1 -17.1(11) . . . . ? C5 N2 Zn1 O1 162.8(10) . . . . ? C6 N1 Zn1 O3 -178.9(7) 2_545 . . . ? C7 N1 Zn1 O3 57.5(9) . . . . ? C6 N1 Zn1 N2 10.1(7) 2_545 . . . ? C7 N1 Zn1 N2 -113.5(7) . . . . ? C6 N1 Zn1 O2 -78.5(7) 2_545 . . . ? C7 N1 Zn1 O2 157.9(7) . . . . ? C6 N1 Zn1 O1 98.0(7) 2_545 . . . ? C7 N1 Zn1 O1 -25.6(7) . . . . ? C8 O2 Zn1 O3 92.1(11) 4_655 . . . ? C8 O2 Zn1 N2 -159.5(11) 4_655 . . . ? C8 O2 Zn1 N1 -43.6(11) 4_655 . . . ? C8 O2 Zn1 O1 -61(2) 4_655 . . . ? C8 O1 Zn1 O3 -116.5(8) . . . . ? C8 O1 Zn1 N2 134.8(8) . . . . ? C8 O1 Zn1 N1 19.0(8) . . . . ? C8 O1 Zn1 O2 36.5(19) . . . . ? _diffrn_measured_fraction_theta_max 0.861 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.139 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.161 data_ValZnBF4 _database_code_depnum_ccdc_archive 'CCDC 926615' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ValZnBF4 _chemical_melting_point ? _chemical_formula_moiety 'C22 H31 N4 O4 Zn, B F4, H2O' _chemical_formula_sum 'C22 H33 B F4 N4 O5 Zn' _chemical_formula_weight 585.73 _chemical_absolute_configuration syn 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.2288(7) _cell_length_b 17.0237(14) _cell_length_c 9.8162(8) _cell_angle_alpha 90.00 _cell_angle_beta 106.686(9) _cell_angle_gamma 90.00 _cell_volume 1317.20(19) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 29.08 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 1.000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.705 _exptl_absorpt_correction_T_max 0.819 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6515 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 29.08 _reflns_number_total 4545 _reflns_number_gt 4426 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; OMIT 3 0 0 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^)+(0.1253P)^2^+0.5621P] 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 0.023(17) _refine_ls_number_reflns 4545 _refine_ls_number_parameters 313 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1705 _refine_ls_wR_factor_gt 0.1659 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 B1 B 0.532(3) 0.4758(15) 0.029(2) 0.131(6) Uiso 1 1 d . . . C1 C 0.4532(7) 0.6513(4) 0.7030(5) 0.0400(11) Uani 1 1 d . . . H1 H 0.4040 0.6211 0.6228 0.048 Uiso 1 1 calc R . . C2 C 0.6105(7) 0.6305(4) 0.7875(6) 0.0424(12) Uani 1 1 d . . . H2 H 0.6662 0.5870 0.7652 0.051 Uiso 1 1 calc R . . C3 C 0.6864(6) 0.6759(4) 0.9086(5) 0.0367(10) Uani 1 1 d . . . C4 C 0.6023(6) 0.7413(4) 0.9320(5) 0.0407(12) Uani 1 1 d . . . H4 H 0.6528 0.7747 1.0072 0.049 Uiso 1 1 calc R . . C5 C 0.4419(6) 0.7578(4) 0.8438(5) 0.0398(11) Uani 1 1 d . . . H5 H 0.3842 0.8013 0.8638 0.048 Uiso 1 1 calc R . . C6 C -0.1504(7) 0.6476(4) 0.0136(7) 0.0543(15) Uani 1 1 d . . . H6A H -0.1748 0.6299 0.0995 0.065 Uiso 1 1 calc R . . H6B H -0.1073 0.6031 -0.0270 0.065 Uiso 1 1 calc R . . C7 C 0.1224(6) 0.6890(4) 0.1813(4) 0.0356(10) Uani 1 1 d . . . H7 H 0.1259 0.6318 0.1937 0.043 Uiso 1 1 calc R . . C8 C 0.0747(5) 0.7265(4) 0.3080(4) 0.0325(9) Uani 1 1 d . . . C9 C 0.2924(6) 0.7158(5) 0.1655(5) 0.0487(19) Uani 1 1 d . . . H9 H 0.2950 0.7014 0.0695 0.058 Uiso 1 1 calc R . . C10 C 0.4373(8) 0.6742(7) 0.2687(8) 0.073(2) Uani 1 1 d . . . H10A H 0.4686 0.7021 0.3574 0.110 Uiso 1 1 calc R . . H10B H 0.5325 0.6722 0.2307 0.110 Uiso 1 1 calc R . . H10C H 0.4034 0.6217 0.2838 0.110 Uiso 1 1 calc R . . C11 C 0.3150(9) 0.8057(6) 0.1791(8) 0.067(2) Uani 1 1 d . . . H11A H 0.2192 0.8311 0.1147 0.101 Uiso 1 1 calc R . . H11B H 0.4166 0.8206 0.1562 0.101 Uiso 1 1 calc R . . H11C H 0.3233 0.8214 0.2748 0.101 Uiso 1 1 calc R . . C12 C -0.1335(7) 0.6136(3) 0.4677(6) 0.0411(11) Uani 1 1 d . . . H12 H -0.1739 0.6564 0.4087 0.049 Uiso 1 1 calc R . . C13 C -0.1931(7) 0.5395(3) 0.4220(6) 0.0400(11) Uani 1 1 d . . . H13 H -0.2723 0.5327 0.3337 0.048 Uiso 1 1 calc R . . C14 C -0.1334(7) 0.4749(3) 0.5097(5) 0.0373(10) Uani 1 1 d . . . C15 C -0.0260(9) 0.4903(3) 0.6445(6) 0.0461(12) Uani 1 1 d . . . H15 H 0.0093 0.4496 0.7094 0.055 Uiso 1 1 calc R . . C16 C 0.0279(8) 0.5654(4) 0.6816(5) 0.0429(12) Uani 1 1 d . . . H16 H 0.1007 0.5740 0.7722 0.052 Uiso 1 1 calc R . . C17 C 0.1794(6) 0.8931(3) 0.5459(6) 0.0366(10) Uani 1 1 d . . . H17A H 0.2271 0.8650 0.4805 0.044 Uiso 1 1 calc R . . H17B H 0.2662 0.8962 0.6367 0.044 Uiso 1 1 calc R . . C18 C -0.0490(6) 0.8806(3) 0.6685(5) 0.0346(10) Uani 1 1 d . . . H18 H -0.0012 0.9330 0.6960 0.042 Uiso 1 1 calc R . . C19 C -0.0138(6) 0.8299(3) 0.8042(5) 0.0366(10) Uani 1 1 d . . . C20 C -0.2429(8) 0.8889(4) 0.6114(7) 0.0508(14) Uani 1 1 d . . . H20 H -0.2820 0.9024 0.6938 0.061 Uiso 1 1 calc R . . C21 C -0.3285(8) 0.8137(5) 0.5555(8) 0.0598(17) Uani 1 1 d . . . H21A H -0.2973 0.7984 0.4722 0.090 Uiso 1 1 calc R . . H21B H -0.4492 0.8205 0.5313 0.090 Uiso 1 1 calc R . . H21C H -0.2942 0.7736 0.6268 0.090 Uiso 1 1 calc R . . C22 C -0.2952(12) 0.9566(7) 0.5092(12) 0.096(4) Uani 1 1 d . . . H22A H -0.2479 1.0045 0.5556 0.144 Uiso 1 1 calc R . . H22B H -0.4167 0.9605 0.4787 0.144 Uiso 1 1 calc R . . H22C H -0.2545 0.9479 0.4281 0.144 Uiso 1 1 calc R . . F1 F 0.4792(15) 0.5481(8) 0.0240(12) 0.173(4) Uiso 1 1 d . . . F2 F 0.4826(16) 0.4547(8) 0.1643(12) 0.180(4) Uiso 1 1 d . . . F3 F 0.695(2) 0.4652(14) 0.0662(19) 0.271(8) Uiso 1 1 d . . . F4 F 0.4256(15) 0.4323(7) -0.0776(12) 0.157(3) Uiso 1 1 d . . . N1 N 0.3666(5) 0.7131(2) 0.7302(4) 0.0326(9) Uani 1 1 d . . . N2 N -0.0192(5) 0.7087(3) 0.0507(4) 0.0378(10) Uani 1 1 d . . . H2A H -0.0671 0.7543 0.0652 0.045 Uiso 1 1 calc R . . H2B H 0.0240 0.7157 -0.0229 0.045 Uiso 1 1 calc R . . N3 N -0.0180(6) 0.6264(2) 0.5957(5) 0.0335(9) Uani 1 1 d . . . N4 N 0.0327(5) 0.8476(2) 0.5649(4) 0.0299(8) Uani 1 1 d . . . H4A H -0.0474 0.8457 0.4790 0.036 Uiso 1 1 calc R . . O1 O 0.0516(5) 0.7625(2) 0.8008(4) 0.0377(7) Uani 1 1 d . . . O2 O -0.0540(6) 0.8568(3) 0.9071(4) 0.0510(10) Uani 1 1 d . . . O3 O 0.1698(4) 0.7081(2) 0.4300(3) 0.0373(9) Uani 1 1 d . . . O4 O -0.0494(5) 0.7720(3) 0.2846(4) 0.0487(10) Uani 1 1 d . . . O5 O 0.8781(10) 0.0148(4) 0.9654(10) 0.101(2) Uani 1 1 d . . . Zn1 Zn 0.11617(5) 0.73138(4) 0.62001(4) 0.02850(17) 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 0.035(2) 0.044(3) 0.037(2) -0.010(2) 0.0027(18) 0.003(2) C2 0.033(2) 0.043(3) 0.044(2) -0.009(2) 0.000(2) 0.007(2) C3 0.026(2) 0.042(3) 0.038(2) -0.003(2) 0.0040(18) -0.006(2) C4 0.0300(19) 0.050(4) 0.037(2) -0.011(2) 0.0011(16) -0.003(3) C5 0.034(2) 0.043(3) 0.037(2) -0.0099(19) 0.0020(18) 0.003(2) C6 0.030(2) 0.054(4) 0.065(3) -0.005(3) -0.008(2) -0.004(3) C7 0.028(2) 0.048(3) 0.0224(18) -0.0047(18) -0.0059(15) 0.000(2) C8 0.0284(17) 0.036(2) 0.0283(16) 0.002(2) 0.0007(13) -0.006(2) C9 0.0267(19) 0.085(6) 0.031(2) -0.010(3) 0.0036(16) -0.003(3) C10 0.035(3) 0.117(8) 0.060(4) -0.009(4) -0.001(3) 0.017(4) C11 0.045(3) 0.091(6) 0.058(4) 0.014(4) 0.004(3) -0.026(4) C12 0.034(2) 0.029(3) 0.053(3) 0.004(2) 0.002(2) 0.001(2) C13 0.035(2) 0.028(2) 0.050(3) 0.004(2) 0.001(2) 0.002(2) C14 0.037(2) 0.033(3) 0.044(2) -0.003(2) 0.016(2) -0.004(2) C15 0.062(3) 0.031(3) 0.043(3) 0.010(2) 0.012(2) 0.001(3) C16 0.053(3) 0.044(3) 0.030(2) -0.003(2) 0.008(2) -0.001(3) C17 0.034(2) 0.023(2) 0.051(3) 0.0075(19) 0.010(2) 0.0047(19) C18 0.032(2) 0.027(2) 0.042(2) 0.0029(19) 0.0070(19) 0.005(2) C19 0.033(2) 0.040(3) 0.036(2) -0.001(2) 0.0068(18) 0.000(2) C20 0.038(3) 0.054(4) 0.059(3) 0.012(3) 0.011(2) 0.015(3) C21 0.035(3) 0.069(5) 0.065(4) 0.008(3) -0.002(2) -0.003(3) C22 0.070(5) 0.096(8) 0.119(7) 0.057(7) 0.022(5) 0.045(6) N1 0.0263(15) 0.038(3) 0.0296(16) 0.0003(15) 0.0013(13) 0.0012(16) N2 0.0310(18) 0.049(3) 0.0263(16) 0.0021(15) -0.0030(14) -0.0058(18) N3 0.036(2) 0.024(2) 0.042(2) -0.0021(16) 0.0126(17) -0.0036(17) N4 0.0321(19) 0.0249(19) 0.0305(17) 0.0022(15) 0.0054(14) 0.0006(17) O1 0.0430(18) 0.0370(18) 0.0339(15) 0.0053(14) 0.0124(14) 0.0048(16) O2 0.066(3) 0.047(3) 0.044(2) -0.0032(18) 0.023(2) 0.009(2) O3 0.0350(15) 0.050(2) 0.0235(13) 0.0029(13) 0.0025(12) 0.0053(15) O4 0.044(2) 0.054(3) 0.0410(18) -0.0011(18) 0.0007(15) 0.008(2) O5 0.095(5) 0.060(4) 0.138(6) -0.023(4) 0.016(4) -0.022(4) Zn1 0.0280(2) 0.0244(3) 0.0293(2) 0.0016(2) 0.00230(16) 0.0016(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 F3 1.30(3) . ? B1 F1 1.30(2) . ? B1 F4 1.38(2) . ? B1 F2 1.54(2) . ? C1 N1 1.340(7) . ? C1 C2 1.368(7) . ? C1 H1 0.9300 . ? C2 C3 1.405(7) . ? C2 H2 0.9300 . ? C3 C4 1.364(8) . ? C3 C6 1.518(7) 1_656 ? C4 C5 1.384(7) . ? C4 H4 0.9300 . ? C5 N1 1.345(6) . ? C5 H5 0.9300 . ? C6 N2 1.468(8) . ? C6 C3 1.518(7) 1_454 ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N2 1.503(5) . ? C7 C9 1.521(7) . ? C7 C8 1.546(6) . ? C7 H7 0.9800 . ? C8 O4 1.249(7) . ? C8 O3 1.267(5) . ? C9 C10 1.502(9) . ? C9 C11 1.542(12) . ? C9 H9 0.9800 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N3 1.357(7) . ? C12 C13 1.381(8) . ? C12 H12 0.9300 . ? C13 C14 1.396(8) . ? C13 H13 0.9300 . ? C14 C15 1.389(8) . ? C14 C17 1.505(7) 2_546 ? C15 C16 1.367(8) . ? C15 H15 0.9300 . ? C16 N3 1.323(7) . ? C16 H16 0.9300 . ? C17 N4 1.490(6) . ? C17 C14 1.505(7) 2_556 ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 N4 1.481(6) . ? C18 C20 1.538(7) . ? C18 C19 1.544(7) . ? C18 H18 0.9800 . ? C19 O2 1.238(7) . ? C19 O1 1.271(7) . ? C20 C21 1.489(11) . ? C20 C22 1.507(10) . ? C20 H20 0.9800 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? N1 Zn1 2.057(4) . ? N2 H2A 0.9000 . ? N2 H2B 0.9000 . ? N3 Zn1 2.079(4) . ? N4 Zn1 2.113(4) . ? N4 H4A 0.9100 . ? O1 Zn1 2.063(3) . ? O3 Zn1 2.075(3) . ? 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 F3 B1 F1 117(2) . . ? F3 B1 F4 121(2) . . ? F1 B1 F4 110.1(17) . . ? F3 B1 F2 103.8(15) . . ? F1 B1 F2 95.0(16) . . ? F4 B1 F2 105.3(17) . . ? N1 C1 C2 123.2(5) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C1 C2 C3 118.9(5) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 117.9(4) . . ? C4 C3 C6 122.5(5) . 1_656 ? C2 C3 C6 119.4(5) . 1_656 ? C3 C4 C5 120.0(5) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? N1 C5 C4 122.2(5) . . ? N1 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? N2 C6 C3 112.8(6) . 1_454 ? N2 C6 H6A 109.0 . . ? C3 C6 H6A 109.0 1_454 . ? N2 C6 H6B 109.0 . . ? C3 C6 H6B 109.0 1_454 . ? H6A C6 H6B 107.8 . . ? N2 C7 C9 110.8(4) . . ? N2 C7 C8 106.2(4) . . ? C9 C7 C8 114.3(4) . . ? N2 C7 H7 108.4 . . ? C9 C7 H7 108.4 . . ? C8 C7 H7 108.4 . . ? O4 C8 O3 125.3(4) . . ? O4 C8 C7 119.4(4) . . ? O3 C8 C7 115.3(4) . . ? C10 C9 C7 111.4(6) . . ? C10 C9 C11 110.9(6) . . ? C7 C9 C11 112.4(5) . . ? C10 C9 H9 107.3 . . ? C7 C9 H9 107.3 . . ? C11 C9 H9 107.3 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 C13 122.4(5) . . ? N3 C12 H12 118.8 . . ? C13 C12 H12 118.8 . . ? C12 C13 C14 119.3(5) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C15 C14 C13 117.0(5) . . ? C15 C14 C17 123.1(5) . 2_546 ? C13 C14 C17 119.9(5) . 2_546 ? C16 C15 C14 120.0(5) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? N3 C16 C15 123.5(5) . . ? N3 C16 H16 118.2 . . ? C15 C16 H16 118.2 . . ? N4 C17 C14 113.5(4) . 2_556 ? N4 C17 H17A 108.9 . . ? C14 C17 H17A 108.9 2_556 . ? N4 C17 H17B 108.9 . . ? C14 C17 H17B 108.9 2_556 . ? H17A C17 H17B 107.7 . . ? N4 C18 C20 114.3(4) . . ? N4 C18 C19 111.7(4) . . ? C20 C18 C19 106.5(4) . . ? N4 C18 H18 108.0 . . ? C20 C18 H18 108.0 . . ? C19 C18 H18 108.0 . . ? O2 C19 O1 124.7(5) . . ? O2 C19 C18 117.9(5) . . ? O1 C19 C18 117.3(4) . . ? C21 C20 C22 113.4(7) . . ? C21 C20 C18 112.8(5) . . ? C22 C20 C18 112.4(6) . . ? C21 C20 H20 105.8 . . ? C22 C20 H20 105.8 . . ? C18 C20 H20 105.8 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C1 N1 C5 117.7(4) . . ? C1 N1 Zn1 121.6(3) . . ? C5 N1 Zn1 120.3(3) . . ? C6 N2 C7 112.8(5) . . ? C6 N2 H2A 109.0 . . ? C7 N2 H2A 109.0 . . ? C6 N2 H2B 109.0 . . ? C7 N2 H2B 109.0 . . ? H2A N2 H2B 107.8 . . ? C16 N3 C12 117.4(5) . . ? C16 N3 Zn1 123.8(4) . . ? C12 N3 Zn1 116.8(3) . . ? C18 N4 C17 115.6(4) . . ? C18 N4 Zn1 111.0(3) . . ? C17 N4 Zn1 107.6(3) . . ? C18 N4 H4A 107.4 . . ? C17 N4 H4A 107.4 . . ? Zn1 N4 H4A 107.4 . . ? C19 O1 Zn1 118.0(3) . . ? C8 O3 Zn1 124.7(3) . . ? N1 Zn1 O1 93.02(15) . . ? N1 Zn1 O3 90.27(14) . . ? O1 Zn1 O3 175.24(15) . . ? N1 Zn1 N3 110.45(17) . . ? O1 Zn1 N3 93.47(16) . . ? O3 Zn1 N3 88.60(16) . . ? N1 Zn1 N4 118.61(17) . . ? O1 Zn1 N4 80.47(16) . . ? O3 Zn1 N4 94.93(15) . . ? N3 Zn1 N4 130.76(17) . . ? 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 -0.3(9) . . . . ? C1 C2 C3 C4 -3.2(9) . . . . ? C1 C2 C3 C6 172.0(6) . . . 1_656 ? C2 C3 C4 C5 4.7(8) . . . . ? C6 C3 C4 C5 -170.3(6) 1_656 . . . ? C3 C4 C5 N1 -2.9(9) . . . . ? N2 C7 C8 O4 -8.8(7) . . . . ? C9 C7 C8 O4 113.7(6) . . . . ? N2 C7 C8 O3 171.9(5) . . . . ? C9 C7 C8 O3 -65.6(7) . . . . ? N2 C7 C9 C10 -160.9(6) . . . . ? C8 C7 C9 C10 79.1(7) . . . . ? N2 C7 C9 C11 73.9(6) . . . . ? C8 C7 C9 C11 -46.1(6) . . . . ? N3 C12 C13 C14 0.0(9) . . . . ? C12 C13 C14 C15 5.0(8) . . . . ? C12 C13 C14 C17 -172.0(5) . . . 2_546 ? C13 C14 C15 C16 -5.4(9) . . . . ? C17 C14 C15 C16 171.5(6) 2_546 . . . ? C14 C15 C16 N3 0.6(10) . . . . ? N4 C18 C19 O2 169.8(5) . . . . ? C20 C18 C19 O2 -64.7(7) . . . . ? N4 C18 C19 O1 -11.6(7) . . . . ? C20 C18 C19 O1 113.9(5) . . . . ? N4 C18 C20 C21 55.2(7) . . . . ? C19 C18 C20 C21 -68.7(6) . . . . ? N4 C18 C20 C22 -74.5(8) . . . . ? C19 C18 C20 C22 161.6(7) . . . . ? C2 C1 N1 C5 2.3(8) . . . . ? C2 C1 N1 Zn1 -169.7(5) . . . . ? C4 C5 N1 C1 -0.7(8) . . . . ? C4 C5 N1 Zn1 171.4(4) . . . . ? C3 C6 N2 C7 164.5(5) 1_454 . . . ? C9 C7 N2 C6 142.4(5) . . . . ? C8 C7 N2 C6 -93.0(6) . . . . ? C15 C16 N3 C12 4.5(9) . . . . ? C15 C16 N3 Zn1 -159.3(5) . . . . ? C13 C12 N3 C16 -4.8(8) . . . . ? C13 C12 N3 Zn1 160.1(4) . . . . ? C20 C18 N4 C17 129.4(5) . . . . ? C19 C18 N4 C17 -109.6(5) . . . . ? C20 C18 N4 Zn1 -107.7(4) . . . . ? C19 C18 N4 Zn1 13.4(5) . . . . ? C14 C17 N4 C18 -61.8(6) 2_556 . . . ? C14 C17 N4 Zn1 173.5(3) 2_556 . . . ? O2 C19 O1 Zn1 -177.9(4) . . . . ? C18 C19 O1 Zn1 3.6(6) . . . . ? O4 C8 O3 Zn1 12.5(8) . . . . ? C7 C8 O3 Zn1 -168.3(3) . . . . ? C1 N1 Zn1 O1 137.7(4) . . . . ? C5 N1 Zn1 O1 -34.1(4) . . . . ? C1 N1 Zn1 O3 -45.8(4) . . . . ? C5 N1 Zn1 O3 142.4(4) . . . . ? C1 N1 Zn1 N3 42.8(4) . . . . ? C5 N1 Zn1 N3 -129.0(4) . . . . ? C1 N1 Zn1 N4 -141.6(4) . . . . ? C5 N1 Zn1 N4 46.7(4) . . . . ? C19 O1 Zn1 N1 121.9(4) . . . . ? C19 O1 Zn1 O3 -12(2) . . . . ? C19 O1 Zn1 N3 -127.4(4) . . . . ? C19 O1 Zn1 N4 3.3(4) . . . . ? C8 O3 Zn1 N1 -162.7(4) . . . . ? C8 O3 Zn1 O1 -29(2) . . . . ? C8 O3 Zn1 N3 86.8(5) . . . . ? C8 O3 Zn1 N4 -44.0(5) . . . . ? C16 N3 Zn1 N1 24.6(5) . . . . ? C12 N3 Zn1 N1 -139.3(4) . . . . ? C16 N3 Zn1 O1 -70.0(4) . . . . ? C12 N3 Zn1 O1 126.1(4) . . . . ? C16 N3 Zn1 O3 114.3(4) . . . . ? C12 N3 Zn1 O3 -49.6(4) . . . . ? C16 N3 Zn1 N4 -150.4(4) . . . . ? C12 N3 Zn1 N4 45.7(5) . . . . ? C18 N4 Zn1 N1 -97.6(3) . . . . ? C17 N4 Zn1 N1 29.8(4) . . . . ? C18 N4 Zn1 O1 -9.3(3) . . . . ? C17 N4 Zn1 O1 118.1(3) . . . . ? C18 N4 Zn1 O3 169.4(3) . . . . ? C17 N4 Zn1 O3 -63.2(3) . . . . ? C18 N4 Zn1 N3 77.0(4) . . . . ? C17 N4 Zn1 N3 -155.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.850 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.100 _refine_diff_density_min -0.869 _refine_diff_density_rms 0.097 data_ValZnClO4 _database_code_depnum_ccdc_archive 'CCDC 926616' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ValZnClO4 _chemical_melting_point ? _chemical_formula_moiety 'C22 H31 N4 O4 Zn, Cl O4, H2O' _chemical_formula_sum 'C22 H33 Cl N4 O9 Zn' _chemical_formula_weight 598.39 _chemical_absolute_configuration syn 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' Cl Cl 0.1484 0.1585 '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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.7650(5) _cell_length_b 16.6683(7) _cell_length_c 14.6753(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.662(4) _cell_angle_gamma 90.00 _cell_volume 2587.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 1.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.677 _exptl_absorpt_correction_T_max 0.801 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13789 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 29.13 _reflns_number_total 8553 _reflns_number_gt 8026 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+5.8110P] 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 -0.023(11) _refine_ls_number_reflns 8553 _refine_ls_number_parameters 675 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1121 _refine_ls_wR_factor_gt 0.1085 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.9203(4) 0.7751(3) 0.5692(3) 0.0144(9) Uani 1 1 d . . . H1 H 0.9006 0.7238 0.5460 0.017 Uiso 1 1 calc R . . C2 C 1.0460(4) 0.7966(3) 0.5929(3) 0.0147(9) Uani 1 1 d . . . H2 H 1.1096 0.7599 0.5883 0.018 Uiso 1 1 calc R . . C3 C 1.0753(4) 0.8746(3) 0.6241(3) 0.0133(9) Uani 1 1 d . . . C4 C 0.9776(4) 0.9245(3) 0.6380(3) 0.0161(9) Uani 1 1 d . . . H4 H 0.9948 0.9757 0.6625 0.019 Uiso 1 1 calc R . . C5 C 0.8549(4) 0.8978(3) 0.6153(3) 0.0155(9) Uani 1 1 d . . . H5 H 0.7900 0.9312 0.6262 0.019 Uiso 1 1 calc R . . C6 C 0.2103(4) 0.9034(3) 0.6361(3) 0.0163(9) Uani 1 1 d . . . H6A H 0.2445 0.8892 0.5816 0.020 Uiso 1 1 calc R . . H6B H 0.2121 0.9614 0.6418 0.020 Uiso 1 1 calc R . . C7 C 0.4296(4) 0.8747(3) 0.7206(3) 0.0128(8) Uani 1 1 d . . . H7A H 0.4476 0.9306 0.7073 0.015 Uiso 1 1 calc R . . C8 C 0.4658(4) 0.8221(3) 0.6440(3) 0.0137(8) Uani 1 1 d . . . C9 C 0.5044(4) 0.8537(3) 0.8184(3) 0.0198(11) Uani 1 1 d . . . H9 H 0.4531 0.8707 0.8636 0.024 Uiso 1 1 calc R . . C10 C 0.6284(4) 0.9022(4) 0.8380(4) 0.0294(13) Uani 1 1 d . . . H10A H 0.6745 0.8890 0.8986 0.044 Uiso 1 1 calc R . . H10B H 0.6093 0.9585 0.8352 0.044 Uiso 1 1 calc R . . H10C H 0.6787 0.8893 0.7923 0.044 Uiso 1 1 calc R . . C11 C 0.5274(5) 0.7647(4) 0.8312(3) 0.0219(11) Uani 1 1 d . . . H11A H 0.4487 0.7365 0.8148 0.033 Uiso 1 1 calc R . . H11B H 0.5637 0.7539 0.8947 0.033 Uiso 1 1 calc R . . H11C H 0.5844 0.7472 0.7920 0.033 Uiso 1 1 calc R . . C12 C 0.4336(4) 0.9157(3) 0.4449(3) 0.0150(9) Uani 1 1 d . . . H12 H 0.3858 0.8708 0.4535 0.018 Uiso 1 1 calc R . . C13 C 0.3733(4) 0.9886(3) 0.4291(3) 0.0161(9) Uani 1 1 d . . . H13 H 0.2865 0.9920 0.4264 0.019 Uiso 1 1 calc R . . C14 C 0.4417(4) 1.0568(3) 0.4171(3) 0.0143(9) Uani 1 1 d . . . C15 C 0.5693(4) 1.0470(3) 0.4130(3) 0.0176(9) Uani 1 1 d . . . H15 H 0.6171 1.0905 0.3998 0.021 Uiso 1 1 calc R . . C16 C 0.6248(4) 0.9709(3) 0.4289(3) 0.0151(9) Uani 1 1 d . . . H16 H 0.7098 0.9648 0.4260 0.018 Uiso 1 1 calc R . . C17 C 0.6160(4) 0.6388(3) 0.5847(3) 0.0164(9) Uani 1 1 d . . . H17A H 0.6006 0.6673 0.6392 0.020 Uiso 1 1 calc R . . H17B H 0.7068 0.6336 0.5896 0.020 Uiso 1 1 calc R . . C18 C 0.5784(5) 0.6469(3) 0.4117(3) 0.0209(11) Uani 1 1 d . . . H18 H 0.6105 0.5924 0.4259 0.025 Uiso 1 1 calc R . . C19 C 0.6746(4) 0.6925(3) 0.3663(3) 0.0185(10) Uani 1 1 d . . . C20 C 0.4559(7) 0.6411(4) 0.3386(5) 0.053(2) Uani 1 1 d . . . H20 H 0.4858 0.6169 0.2857 0.064 Uiso 1 1 calc R . . C21 C 0.3683(7) 0.5804(6) 0.3610(6) 0.064(3) Uani 1 1 d . . . H21A H 0.4152 0.5362 0.3920 0.096 Uiso 1 1 calc R . . H21B H 0.3157 0.5618 0.3049 0.096 Uiso 1 1 calc R . . H21C H 0.3163 0.6035 0.4007 0.096 Uiso 1 1 calc R . . C22 C 0.4066(5) 0.7190(4) 0.3007(4) 0.0317(13) Uani 1 1 d . . . H22A H 0.3802 0.7501 0.3489 0.047 Uiso 1 1 calc R . . H22B H 0.3357 0.7104 0.2514 0.047 Uiso 1 1 calc R . . H22C H 0.4716 0.7474 0.2772 0.047 Uiso 1 1 calc R . . C23 C -0.0673(4) 0.9362(3) -0.0013(3) 0.0154(9) Uani 1 1 d . . . H23 H -0.1060 0.8929 0.0221 0.018 Uiso 1 1 calc R . . C24 C -0.1337(4) 1.0075(3) -0.0175(3) 0.0146(9) Uani 1 1 d . . . H24 H -0.2150 1.0118 -0.0050 0.017 Uiso 1 1 calc R . . C25 C -0.0770(4) 1.0727(3) -0.0530(3) 0.0130(9) Uani 1 1 d . . . C26 C 0.0437(5) 1.0617(3) -0.0739(3) 0.0196(10) Uani 1 1 d . . . H26 H 0.0835 1.1031 -0.0997 0.024 Uiso 1 1 calc R . . C27 C 0.1031(5) 0.9875(3) -0.0551(3) 0.0184(10) Uani 1 1 d . . . H27 H 0.1829 0.9803 -0.0696 0.022 Uiso 1 1 calc R . . C28 C 0.1403(4) 0.6538(3) 0.0615(3) 0.0150(9) Uani 1 1 d . . . H28A H 0.1387 0.6757 0.1225 0.018 Uiso 1 1 calc R . . H28B H 0.2280 0.6475 0.0556 0.018 Uiso 1 1 calc R . . C29 C 0.0845(4) 0.6885(3) -0.1075(3) 0.0111(8) Uani 1 1 d . . . H29 H 0.1205 0.6344 -0.1067 0.013 Uiso 1 1 calc R . . C30 C 0.1732(4) 0.7465(3) -0.1470(3) 0.0110(8) Uani 1 1 d . . . C31 C -0.0440(4) 0.6879(3) -0.1738(3) 0.0152(9) Uani 1 1 d . . . H31 H -0.0272 0.6768 -0.2360 0.018 Uiso 1 1 calc R . . C32 C -0.1085(4) 0.7698(3) -0.1781(3) 0.0212(10) Uani 1 1 d . . . H32A H -0.1326 0.7810 -0.1196 0.032 Uiso 1 1 calc R . . H32B H -0.1823 0.7695 -0.2261 0.032 Uiso 1 1 calc R . . H32C H -0.0510 0.8104 -0.1912 0.032 Uiso 1 1 calc R . . C33 C -0.1326(4) 0.6219(3) -0.1518(4) 0.0230(11) Uani 1 1 d . . . H33A H -0.0898 0.5711 -0.1481 0.034 Uiso 1 1 calc R . . H33B H -0.2064 0.6198 -0.1998 0.034 Uiso 1 1 calc R . . H33C H -0.1573 0.6332 -0.0935 0.034 Uiso 1 1 calc R . . C34 C 0.4305(4) 0.7978(3) 0.0627(3) 0.0174(9) Uani 1 1 d . . . H34 H 0.4087 0.7586 0.0175 0.021 Uiso 1 1 calc R . . C35 C 0.5575(4) 0.8101(3) 0.0995(3) 0.0158(9) Uani 1 1 d . . . H35 H 0.6189 0.7793 0.0789 0.019 Uiso 1 1 calc R . . C36 C 0.5929(4) 0.8685(3) 0.1669(3) 0.0139(9) Uani 1 1 d . . . C37 C 0.4959(4) 0.9115(3) 0.1959(3) 0.0152(9) Uani 1 1 d . . . H37 H 0.5148 0.9506 0.2415 0.018 Uiso 1 1 calc R . . C38 C 0.3709(4) 0.8954(3) 0.1561(3) 0.0160(9) Uani 1 1 d . . . H38 H 0.3073 0.9243 0.1763 0.019 Uiso 1 1 calc R . . C39 C -0.2702(4) 0.8886(3) 0.2025(3) 0.0182(10) Uani 1 1 d . . . H39A H -0.2330 0.9091 0.1518 0.022 Uiso 1 1 calc R . . H39B H -0.2651 0.9305 0.2490 0.022 Uiso 1 1 calc R . . C40 C -0.0550(4) 0.8294(3) 0.2563(3) 0.0151(9) Uani 1 1 d . . . H40 H -0.0367 0.8866 0.2670 0.018 Uiso 1 1 calc R . . C41 C -0.0169(4) 0.8052(3) 0.1647(3) 0.0131(8) Uani 1 1 d . . . C42 C 0.1436(4) 0.8191(4) 0.3766(3) 0.0253(11) Uani 1 1 d . . . H42A H 0.1902 0.8229 0.3270 0.038 Uiso 1 1 calc R . . H42B H 0.1893 0.7863 0.4252 0.038 Uiso 1 1 calc R . . H42C H 0.1322 0.8717 0.4003 0.038 Uiso 1 1 calc R . . C43 C 0.0150(4) 0.7816(3) 0.3405(3) 0.0201(11) Uani 1 1 d . . . H43 H -0.0348 0.7869 0.3898 0.024 Uiso 1 1 calc R . . C44 C 0.0252(5) 0.6915(3) 0.3212(4) 0.0271(12) Uani 1 1 d . . . H44A H -0.0563 0.6712 0.2930 0.041 Uiso 1 1 calc R . . H44B H 0.0544 0.6637 0.3785 0.041 Uiso 1 1 calc R . . H44C H 0.0838 0.6833 0.2801 0.041 Uiso 1 1 calc R . . Cl1 Cl 0.00884(11) 0.54068(8) 0.57471(9) 0.0247(3) Uani 1 1 d . . . Cl2 Cl 0.47134(15) 0.07914(10) 1.02254(11) 0.0370(3) Uani 1 1 d . . . N1 N 0.8252(3) 0.8248(2) 0.5779(2) 0.0119(7) Uani 1 1 d . . . N2 N 0.5589(3) 0.9064(3) 0.4484(3) 0.0150(8) Uani 1 1 d . . . N3 N 0.0504(4) 0.9268(2) -0.0176(3) 0.0128(8) Uani 1 1 d . . . N4 N 0.3382(3) 0.8403(2) 0.0901(2) 0.0115(7) Uani 1 1 d . . . N5 N 0.2910(3) 0.8673(3) 0.7203(3) 0.0137(8) Uani 1 1 d . . . H5A H 0.2733 0.8915 0.7712 0.016 Uiso 1 1 calc R . . H5B H 0.2712 0.8150 0.7233 0.016 Uiso 1 1 calc R . . N6 N 0.5638(4) 0.6862(2) 0.5004(3) 0.0158(8) Uani 1 1 d . . . H6 H 0.4794 0.6917 0.4991 0.019 Uiso 1 1 calc R . . N7 N 0.0774(3) 0.7109(2) -0.0102(3) 0.0102(7) Uani 1 1 d . . . H7 H -0.0059 0.7126 -0.0060 0.012 Uiso 1 1 calc R . . N8 N -0.1961(3) 0.8170(2) 0.2442(2) 0.0132(7) Uani 1 1 d . . . H8A H -0.2181 0.7742 0.2075 0.016 Uiso 1 1 calc R . . H8B H -0.2163 0.8064 0.2998 0.016 Uiso 1 1 calc R . . O1 O 0.5766(3) 0.8356(2) 0.6290(2) 0.0153(7) Uani 1 1 d . . . O2 O 0.3890(3) 0.7724(2) 0.6019(2) 0.0178(7) Uani 1 1 d . . . O3 O 0.7078(3) 0.7630(2) 0.3958(2) 0.0151(7) Uani 1 1 d . . . O4 O 0.7129(4) 0.6607(3) 0.3003(3) 0.0341(9) Uani 1 1 d . . . O5 O 0.2102(3) 0.8104(2) -0.10252(19) 0.0123(6) Uani 1 1 d . . . O6 O 0.2009(3) 0.7278(2) -0.2230(2) 0.0150(7) Uani 1 1 d . . . O7 O 0.0918(2) 0.8276(2) 0.1535(2) 0.0131(6) Uani 1 1 d . . . O8 O -0.0955(3) 0.7653(2) 0.1087(2) 0.0160(7) Uani 1 1 d . . . O9 O -0.0994(3) 0.5426(3) 0.4996(3) 0.0374(11) Uani 1 1 d . . . O10 O 0.0670(4) 0.4625(2) 0.5805(3) 0.0277(8) Uani 1 1 d . . . O11 O 0.0989(4) 0.5998(3) 0.5585(4) 0.0543(15) Uani 1 1 d . . . O12 O -0.0355(5) 0.5567(4) 0.6601(4) 0.0692(19) Uani 1 1 d . . . O13 O 0.3830(5) 0.1302(3) 0.9680(4) 0.0570(15) Uani 1 1 d . . . O14 O 0.5950(6) 0.1074(4) 1.0286(5) 0.084(2) Uani 1 1 d . . . O15 O 0.4432(5) 0.0776(3) 1.1154(4) 0.0523(13) Uani 1 1 d . . . O16 O 0.4618(7) -0.0008(3) 0.9840(4) 0.0660(17) Uani 1 1 d . . . O17 O 0.7040(4) 0.5214(2) 0.2002(3) 0.0300(9) Uani 1 1 d . . . O18 O 0.2939(4) 0.5686(3) 0.7582(3) 0.0352(10) Uani 1 1 d . . . Zn1 Zn 0.64239(4) 0.80302(3) 0.51264(3) 0.01103(12) Uani 1 1 d . . . Zn2 Zn 0.15244(4) 0.82488(3) 0.02446(3) 0.01037(12) 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 0.015(2) 0.016(2) 0.012(2) 0.0017(17) 0.0033(16) 0.0002(17) C2 0.0094(17) 0.022(2) 0.013(2) 0.0017(19) 0.0021(14) 0.0044(18) C3 0.0104(19) 0.019(2) 0.010(2) 0.0062(18) -0.0005(15) 0.0009(17) C4 0.018(2) 0.015(2) 0.015(2) -0.0016(18) 0.0018(16) -0.0028(18) C5 0.0125(19) 0.017(2) 0.017(2) 0.0004(18) 0.0039(16) 0.0046(16) C6 0.0108(19) 0.023(3) 0.015(2) 0.0038(19) 0.0002(16) -0.0009(17) C7 0.0077(17) 0.015(2) 0.016(2) -0.0002(18) 0.0023(15) -0.0028(15) C8 0.0106(17) 0.016(2) 0.0151(19) 0.0052(19) 0.0033(14) 0.0003(18) C9 0.011(2) 0.030(3) 0.017(2) -0.004(2) -0.0017(17) 0.0043(18) C10 0.015(2) 0.033(3) 0.036(3) -0.012(3) -0.007(2) 0.002(2) C11 0.016(2) 0.036(3) 0.013(2) 0.007(2) -0.0002(17) 0.002(2) C12 0.0144(19) 0.015(2) 0.016(2) 0.0008(18) 0.0026(16) -0.0055(17) C13 0.0105(19) 0.022(3) 0.016(2) -0.0050(19) 0.0011(16) -0.0040(17) C14 0.018(2) 0.010(2) 0.013(2) -0.0010(17) -0.0008(16) 0.0015(17) C15 0.020(2) 0.016(2) 0.020(2) -0.0009(19) 0.0112(18) -0.0018(18) C16 0.014(2) 0.015(2) 0.017(2) 0.0003(19) 0.0046(17) -0.0009(17) C17 0.019(2) 0.015(2) 0.014(2) 0.0015(18) 0.0002(17) -0.0037(18) C18 0.026(2) 0.019(3) 0.015(2) 0.0011(19) -0.0041(19) -0.010(2) C19 0.024(2) 0.017(2) 0.015(2) 0.0010(19) 0.0037(18) -0.0024(19) C20 0.053(4) 0.052(5) 0.039(4) 0.025(3) -0.031(3) -0.034(3) C21 0.044(4) 0.070(6) 0.068(5) 0.021(5) -0.015(4) -0.026(4) C22 0.022(2) 0.042(4) 0.031(3) -0.003(3) 0.005(2) -0.007(2) C23 0.015(2) 0.013(2) 0.018(2) -0.0007(18) 0.0033(17) -0.0014(17) C24 0.016(2) 0.013(2) 0.014(2) -0.0006(18) 0.0008(16) -0.0022(16) C25 0.0162(19) 0.010(2) 0.012(2) -0.0025(17) 0.0014(16) 0.0020(16) C26 0.028(2) 0.013(2) 0.020(2) 0.0031(19) 0.0111(19) 0.0019(19) C27 0.022(2) 0.015(2) 0.020(2) 0.001(2) 0.0109(19) 0.0024(19) C28 0.017(2) 0.013(2) 0.015(2) 0.0007(18) 0.0024(16) -0.0031(17) C29 0.0132(19) 0.010(2) 0.011(2) -0.0008(16) 0.0034(15) -0.0024(15) C30 0.0079(17) 0.012(2) 0.014(2) 0.0030(17) 0.0034(15) 0.0013(15) C31 0.015(2) 0.017(2) 0.014(2) -0.0004(18) 0.0035(16) -0.0041(17) C32 0.013(2) 0.032(3) 0.018(2) 0.002(2) -0.0009(17) -0.0005(19) C33 0.019(2) 0.029(3) 0.018(2) -0.001(2) -0.0015(18) -0.013(2) C34 0.0151(19) 0.017(2) 0.020(2) -0.003(2) 0.0036(16) 0.0029(18) C35 0.0121(18) 0.018(3) 0.018(2) -0.001(2) 0.0051(15) 0.0012(18) C36 0.0134(19) 0.016(2) 0.013(2) 0.0020(18) 0.0037(15) 0.0009(17) C37 0.0127(19) 0.017(2) 0.015(2) -0.0026(19) 0.0016(16) 0.0006(17) C38 0.016(2) 0.017(2) 0.016(2) -0.0032(18) 0.0059(17) 0.0024(17) C39 0.018(2) 0.016(2) 0.020(2) 0.0025(19) 0.0021(18) 0.0011(18) C40 0.0110(17) 0.020(2) 0.015(2) -0.0026(19) 0.0049(15) -0.0005(18) C41 0.0132(17) 0.012(2) 0.0146(19) 0.0027(18) 0.0037(14) 0.0017(17) C42 0.0141(19) 0.039(3) 0.021(2) 0.003(2) 0.0000(16) 0.003(2) C43 0.0109(19) 0.034(3) 0.015(2) 0.002(2) 0.0008(16) 0.0038(19) C44 0.026(3) 0.028(3) 0.025(3) 0.010(2) 0.001(2) 0.003(2) Cl1 0.0213(5) 0.0242(7) 0.0290(7) -0.0107(5) 0.0059(5) -0.0029(5) Cl2 0.0449(8) 0.0289(8) 0.0343(8) 0.0014(6) -0.0006(6) -0.0054(6) N1 0.0112(15) 0.0114(18) 0.0134(16) 0.0011(16) 0.0029(12) -0.0018(14) N2 0.0145(17) 0.015(2) 0.0158(19) -0.0007(16) 0.0039(14) -0.0001(15) N3 0.0163(17) 0.0099(19) 0.0128(19) -0.0036(15) 0.0037(14) 0.0007(14) N4 0.0116(15) 0.011(2) 0.0125(17) -0.0017(14) 0.0046(13) -0.0008(13) N5 0.0105(16) 0.018(2) 0.0126(18) 0.0012(16) 0.0028(13) -0.0001(15) N6 0.0121(17) 0.015(2) 0.021(2) 0.0065(16) 0.0039(15) -0.0003(15) N7 0.0110(16) 0.0100(18) 0.0100(18) 0.0002(15) 0.0030(13) 0.0004(13) N8 0.0103(15) 0.018(2) 0.0123(16) 0.0028(16) 0.0042(12) 0.0004(15) O1 0.0093(13) 0.0200(18) 0.0179(15) -0.0015(14) 0.0059(11) -0.0003(12) O2 0.0139(14) 0.0205(17) 0.0195(16) -0.0032(14) 0.0042(12) -0.0025(13) O3 0.0132(14) 0.0167(17) 0.0167(16) -0.0008(14) 0.0063(12) -0.0020(12) O4 0.054(3) 0.023(2) 0.029(2) -0.0080(18) 0.0162(18) -0.0030(19) O5 0.0132(12) 0.0116(16) 0.0129(13) -0.0005(13) 0.0045(10) -0.0028(12) O6 0.0161(14) 0.0172(17) 0.0131(15) -0.0002(13) 0.0063(12) -0.0006(13) O7 0.0088(12) 0.0187(17) 0.0124(14) -0.0024(14) 0.0039(10) -0.0025(13) O8 0.0167(14) 0.0178(17) 0.0139(15) -0.0033(13) 0.0041(12) -0.0033(13) O9 0.0220(18) 0.048(3) 0.039(2) -0.018(2) -0.0019(16) -0.0001(19) O10 0.0324(19) 0.023(2) 0.030(2) -0.0027(16) 0.0112(16) -0.0026(16) O11 0.030(2) 0.031(3) 0.095(4) 0.015(3) -0.008(2) -0.0137(19) O12 0.077(4) 0.092(5) 0.043(3) -0.034(3) 0.021(3) 0.017(4) O13 0.055(3) 0.053(3) 0.057(3) 0.000(3) -0.004(3) -0.004(3) O14 0.075(4) 0.074(4) 0.128(6) 0.062(4) 0.083(4) 0.045(3) O15 0.072(3) 0.041(3) 0.050(3) 0.006(3) 0.026(3) 0.001(3) O16 0.129(5) 0.030(3) 0.040(3) -0.004(2) 0.019(3) -0.001(3) O17 0.045(2) 0.0179(19) 0.027(2) 0.0015(16) 0.0056(17) 0.0070(17) O18 0.045(2) 0.022(2) 0.036(2) -0.0049(18) 0.0007(19) 0.0075(19) Zn1 0.0077(2) 0.0111(3) 0.0147(2) 0.0013(2) 0.00330(16) -0.00003(18) Zn2 0.0105(2) 0.0087(3) 0.0125(2) -0.00044(19) 0.00370(16) -0.00042(18) _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 1.341(6) . ? C1 C2 1.380(6) . ? C1 H1 0.9300 . ? C2 C3 1.395(7) . ? C2 H2 0.9300 . ? C3 C4 1.386(6) . ? C3 C6 1.509(6) 1_655 ? C4 C5 1.375(6) . ? C4 H4 0.9300 . ? C5 N1 1.348(6) . ? C5 H5 0.9300 . ? C6 N5 1.498(5) . ? C6 C3 1.509(6) 1_455 ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N5 1.497(5) . ? C7 C8 1.532(6) . ? C7 C9 1.550(6) . ? C7 H7A 0.9800 . ? C8 O2 1.250(6) . ? C8 O1 1.272(5) . ? C9 C11 1.510(8) . ? C9 C10 1.541(7) . ? C9 H9 0.9800 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N2 1.348(6) . ? C12 C13 1.377(7) . ? C12 H12 0.9300 . ? C13 C14 1.383(7) . ? C13 H13 0.9300 . ? C14 C15 1.396(6) . ? C14 C17 1.500(6) 2_656 ? C15 C16 1.402(7) . ? C15 H15 0.9300 . ? C16 N2 1.348(6) . ? C16 H16 0.9300 . ? C17 N6 1.489(6) . ? C17 C14 1.500(6) 2_646 ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 N6 1.491(7) . ? C18 C19 1.532(7) . ? C18 C20 1.542(7) . ? C18 H18 0.9800 . ? C19 O4 1.239(6) . ? C19 O3 1.281(6) . ? C20 C21 1.462(9) . ? C20 C22 1.472(9) . ? C20 H20 0.9800 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 N3 1.342(6) . ? C23 C24 1.385(7) . ? C23 H23 0.9300 . ? C24 C25 1.393(6) . ? C24 H24 0.9300 . ? C25 C26 1.401(6) . ? C25 C28 1.509(6) 2 ? C26 C27 1.395(7) . ? C26 H26 0.9300 . ? C27 N3 1.328(6) . ? C27 H27 0.9300 . ? C28 N7 1.487(6) . ? C28 C25 1.509(6) 2_545 ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 N7 1.492(6) . ? C29 C31 1.538(6) . ? C29 C30 1.545(6) . ? C29 H29 0.9800 . ? C30 O6 1.245(5) . ? C30 O5 1.275(5) . ? C31 C32 1.527(7) . ? C31 C33 1.530(6) . ? C31 H31 0.9800 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 N4 1.341(6) . ? C34 C35 1.389(6) . ? C34 H34 0.9300 . ? C35 C36 1.390(7) . ? C35 H35 0.9300 . ? C36 C37 1.396(6) . ? C36 C39 1.507(6) 1_655 ? C37 C38 1.391(6) . ? C37 H37 0.9300 . ? C38 N4 1.334(6) . ? C38 H38 0.9300 . ? C39 N8 1.501(6) . ? C39 C36 1.507(6) 1_455 ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 N8 1.511(5) . ? C40 C41 1.530(6) . ? C40 C43 1.544(6) . ? C40 H40 0.9800 . ? C41 O8 1.256(5) . ? C41 O7 1.268(5) . ? C42 C43 1.522(6) . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C43 C44 1.535(8) . ? C43 H43 0.9800 . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 0.9600 . ? Cl1 O11 1.432(5) . ? Cl1 O10 1.441(4) . ? Cl1 O12 1.446(5) . ? Cl1 O9 1.449(4) . ? Cl2 O14 1.399(7) . ? Cl2 O13 1.409(5) . ? Cl2 O16 1.443(5) . ? Cl2 O15 1.450(5) . ? N1 Zn1 2.056(3) . ? N2 Zn1 2.087(4) . ? N3 Zn2 2.055(4) . ? N4 Zn2 2.069(3) . ? N5 H5A 0.9000 . ? N5 H5B 0.9000 . ? N6 Zn1 2.117(4) . ? N6 H6 0.9100 . ? N7 Zn2 2.090(4) . ? N7 H7 0.9100 . ? N8 H8A 0.9000 . ? N8 H8B 0.9000 . ? O1 Zn1 2.040(3) . ? O3 Zn1 2.080(3) . ? O5 Zn2 2.085(3) . ? O7 Zn2 2.115(3) . ? 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 123.1(5) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C1 C2 C3 118.4(4) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 118.5(4) . . ? C4 C3 C6 122.2(4) . 1_655 ? C2 C3 C6 119.3(4) . 1_655 ? C5 C4 C3 119.3(4) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? N1 C5 C4 122.4(4) . . ? N1 C5 H5 118.8 . . ? C4 C5 H5 118.8 . . ? N5 C6 C3 111.6(4) . 1_455 ? N5 C6 H6A 109.3 . . ? C3 C6 H6A 109.3 1_455 . ? N5 C6 H6B 109.3 . . ? C3 C6 H6B 109.3 1_455 . ? H6A C6 H6B 108.0 . . ? N5 C7 C8 109.8(3) . . ? N5 C7 C9 109.4(4) . . ? C8 C7 C9 113.1(4) . . ? N5 C7 H7A 108.1 . . ? C8 C7 H7A 108.1 . . ? C9 C7 H7A 108.1 . . ? O2 C8 O1 126.0(4) . . ? O2 C8 C7 120.4(4) . . ? O1 C8 C7 113.5(4) . . ? C11 C9 C10 112.1(4) . . ? C11 C9 C7 112.4(4) . . ? C10 C9 C7 109.8(4) . . ? C11 C9 H9 107.5 . . ? C10 C9 H9 107.5 . . ? C7 C9 H9 107.5 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 C13 123.0(4) . . ? N2 C12 H12 118.5 . . ? C13 C12 H12 118.5 . . ? C12 C13 C14 120.1(4) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 117.4(4) . . ? C13 C14 C17 121.5(4) . 2_656 ? C15 C14 C17 120.9(4) . 2_656 ? C14 C15 C16 119.4(4) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? N2 C16 C15 122.2(4) . . ? N2 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? N6 C17 C14 112.2(4) . 2_646 ? N6 C17 H17A 109.2 . . ? C14 C17 H17A 109.2 2_646 . ? N6 C17 H17B 109.2 . . ? C14 C17 H17B 109.2 2_646 . ? H17A C17 H17B 107.9 . . ? N6 C18 C19 110.5(4) . . ? N6 C18 C20 114.8(5) . . ? C19 C18 C20 106.7(4) . . ? N6 C18 H18 108.2 . . ? C19 C18 H18 108.2 . . ? C20 C18 H18 108.2 . . ? O4 C19 O3 122.9(5) . . ? O4 C19 C18 118.5(5) . . ? O3 C19 C18 118.5(4) . . ? C21 C20 C22 119.5(7) . . ? C21 C20 C18 113.0(5) . . ? C22 C20 C18 114.2(5) . . ? C21 C20 H20 102.3 . . ? C22 C20 H20 102.3 . . ? C18 C20 H20 102.3 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N3 C23 C24 122.9(4) . . ? N3 C23 H23 118.5 . . ? C24 C23 H23 118.5 . . ? C23 C24 C25 119.0(4) . . ? C23 C24 H24 120.5 . . ? C25 C24 H24 120.5 . . ? C24 C25 C26 117.9(4) . . ? C24 C25 C28 120.5(4) . 2 ? C26 C25 C28 121.5(4) . 2 ? C27 C26 C25 118.9(5) . . ? C27 C26 H26 120.6 . . ? C25 C26 H26 120.6 . . ? N3 C27 C26 122.8(4) . . ? N3 C27 H27 118.6 . . ? C26 C27 H27 118.6 . . ? N7 C28 C25 112.1(3) . 2_545 ? N7 C28 H28A 109.2 . . ? C25 C28 H28A 109.2 2_545 . ? N7 C28 H28B 109.2 . . ? C25 C28 H28B 109.2 2_545 . ? H28A C28 H28B 107.9 . . ? N7 C29 C31 114.1(4) . . ? N7 C29 C30 110.3(3) . . ? C31 C29 C30 108.2(3) . . ? N7 C29 H29 108.0 . . ? C31 C29 H29 108.0 . . ? C30 C29 H29 108.0 . . ? O6 C30 O5 124.3(4) . . ? O6 C30 C29 116.5(4) . . ? O5 C30 C29 119.1(4) . . ? C32 C31 C33 110.8(4) . . ? C32 C31 C29 111.7(4) . . ? C33 C31 C29 113.2(4) . . ? C32 C31 H31 106.9 . . ? C33 C31 H31 106.9 . . ? C29 C31 H31 106.9 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? N4 C34 C35 122.4(4) . . ? N4 C34 H34 118.8 . . ? C35 C34 H34 118.8 . . ? C34 C35 C36 120.0(4) . . ? C34 C35 H35 120.0 . . ? C36 C35 H35 120.0 . . ? C35 C36 C37 117.0(4) . . ? C35 C36 C39 121.6(4) . 1_655 ? C37 C36 C39 121.2(4) . 1_655 ? C38 C37 C36 119.6(4) . . ? C38 C37 H37 120.2 . . ? C36 C37 H37 120.2 . . ? N4 C38 C37 122.9(4) . . ? N4 C38 H38 118.6 . . ? C37 C38 H38 118.6 . . ? N8 C39 C36 112.1(4) . 1_455 ? N8 C39 H39A 109.2 . . ? C36 C39 H39A 109.2 1_455 . ? N8 C39 H39B 109.2 . . ? C36 C39 H39B 109.2 1_455 . ? H39A C39 H39B 107.9 . . ? N8 C40 C41 106.7(3) . . ? N8 C40 C43 110.8(4) . . ? C41 C40 C43 113.4(4) . . ? N8 C40 H40 108.6 . . ? C41 C40 H40 108.6 . . ? C43 C40 H40 108.6 . . ? O8 C41 O7 126.7(4) . . ? O8 C41 C40 117.2(4) . . ? O7 C41 C40 116.1(4) . . ? C43 C42 H42A 109.5 . . ? C43 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C43 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C42 C43 C44 112.0(4) . . ? C42 C43 C40 110.1(4) . . ? C44 C43 C40 113.5(4) . . ? C42 C43 H43 107.0 . . ? C44 C43 H43 107.0 . . ? C40 C43 H43 107.0 . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? O11 Cl1 O10 109.3(3) . . ? O11 Cl1 O12 111.0(4) . . ? O10 Cl1 O12 108.9(3) . . ? O11 Cl1 O9 109.4(3) . . ? O10 Cl1 O9 110.2(2) . . ? O12 Cl1 O9 107.9(3) . . ? O14 Cl2 O13 111.6(4) . . ? O14 Cl2 O16 109.5(4) . . ? O13 Cl2 O16 110.1(3) . . ? O14 Cl2 O15 107.9(4) . . ? O13 Cl2 O15 107.9(3) . . ? O16 Cl2 O15 109.9(3) . . ? C1 N1 C5 117.9(4) . . ? C1 N1 Zn1 121.9(3) . . ? C5 N1 Zn1 118.9(3) . . ? C16 N2 C12 117.5(4) . . ? C16 N2 Zn1 123.7(3) . . ? C12 N2 Zn1 117.1(3) . . ? C27 N3 C23 118.4(4) . . ? C27 N3 Zn2 120.6(3) . . ? C23 N3 Zn2 120.8(3) . . ? C38 N4 C34 118.1(4) . . ? C38 N4 Zn2 121.7(3) . . ? C34 N4 Zn2 120.1(3) . . ? C7 N5 C6 113.3(4) . . ? C7 N5 H5A 108.9 . . ? C6 N5 H5A 108.9 . . ? C7 N5 H5B 108.9 . . ? C6 N5 H5B 108.9 . . ? H5A N5 H5B 107.7 . . ? C17 N6 C18 114.0(4) . . ? C17 N6 Zn1 109.5(3) . . ? C18 N6 Zn1 111.9(3) . . ? C17 N6 H6 107.0 . . ? C18 N6 H6 107.0 . . ? Zn1 N6 H6 107.0 . . ? C28 N7 C29 114.8(4) . . ? C28 N7 Zn2 107.8(3) . . ? C29 N7 Zn2 112.0(3) . . ? C28 N7 H7 107.3 . . ? C29 N7 H7 107.3 . . ? Zn2 N7 H7 107.3 . . ? C39 N8 C40 112.7(4) . . ? C39 N8 H8A 109.0 . . ? C40 N8 H8A 109.0 . . ? C39 N8 H8B 109.0 . . ? C40 N8 H8B 109.0 . . ? H8A N8 H8B 107.8 . . ? C8 O1 Zn1 125.4(3) . . ? C19 O3 Zn1 117.2(3) . . ? C30 O5 Zn2 116.0(3) . . ? C41 O7 Zn2 123.7(3) . . ? O1 Zn1 N1 90.77(13) . . ? O1 Zn1 O3 176.77(14) . . ? N1 Zn1 O3 89.99(13) . . ? O1 Zn1 N2 88.33(15) . . ? N1 Zn1 N2 111.11(15) . . ? O3 Zn1 N2 94.32(15) . . ? O1 Zn1 N6 96.96(15) . . ? N1 Zn1 N6 122.36(15) . . ? O3 Zn1 N6 79.99(15) . . ? N2 Zn1 N6 126.08(15) . . ? N3 Zn2 N4 117.02(15) . . ? N3 Zn2 O5 93.33(14) . . ? N4 Zn2 O5 90.46(13) . . ? N3 Zn2 N7 121.15(14) . . ? N4 Zn2 N7 121.53(14) . . ? O5 Zn2 N7 81.00(13) . . ? N3 Zn2 O7 90.87(14) . . ? N4 Zn2 O7 90.70(12) . . ? O5 Zn2 O7 174.56(14) . . ? N7 Zn2 O7 93.87(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 -2.6(7) . . . . ? C1 C2 C3 C4 6.0(6) . . . . ? C1 C2 C3 C6 -170.5(4) . . . 1_655 ? C2 C3 C4 C5 -4.1(7) . . . . ? C6 C3 C4 C5 172.3(4) 1_655 . . . ? C3 C4 C5 N1 -1.4(7) . . . . ? N5 C7 C8 O2 -10.9(6) . . . . ? C9 C7 C8 O2 111.6(5) . . . . ? N5 C7 C8 O1 168.4(4) . . . . ? C9 C7 C8 O1 -69.2(5) . . . . ? N5 C7 C9 C11 85.6(5) . . . . ? C8 C7 C9 C11 -37.1(6) . . . . ? N5 C7 C9 C10 -149.0(4) . . . . ? C8 C7 C9 C10 88.3(5) . . . . ? N2 C12 C13 C14 -0.9(7) . . . . ? C12 C13 C14 C15 6.0(7) . . . . ? C12 C13 C14 C17 -169.9(4) . . . 2_656 ? C13 C14 C15 C16 -5.5(7) . . . . ? C17 C14 C15 C16 170.4(4) 2_656 . . . ? C14 C15 C16 N2 -0.1(7) . . . . ? N6 C18 C19 O4 168.6(4) . . . . ? C20 C18 C19 O4 -65.9(7) . . . . ? N6 C18 C19 O3 -14.3(6) . . . . ? C20 C18 C19 O3 111.2(6) . . . . ? N6 C18 C20 C21 -73.8(8) . . . . ? C19 C18 C20 C21 163.4(7) . . . . ? N6 C18 C20 C22 67.2(8) . . . . ? C19 C18 C20 C22 -55.6(8) . . . . ? N3 C23 C24 C25 0.4(7) . . . . ? C23 C24 C25 C26 2.4(6) . . . . ? C23 C24 C25 C28 -173.1(4) . . . 2 ? C24 C25 C26 C27 -2.3(7) . . . . ? C28 C25 C26 C27 173.1(4) 2 . . . ? C25 C26 C27 N3 -0.5(8) . . . . ? N7 C29 C30 O6 170.5(3) . . . . ? C31 C29 C30 O6 -64.1(5) . . . . ? N7 C29 C30 O5 -11.4(5) . . . . ? C31 C29 C30 O5 113.9(4) . . . . ? N7 C29 C31 C32 58.8(5) . . . . ? C30 C29 C31 C32 -64.4(5) . . . . ? N7 C29 C31 C33 -67.1(5) . . . . ? C30 C29 C31 C33 169.8(4) . . . . ? N4 C34 C35 C36 -0.3(8) . . . . ? C34 C35 C36 C37 1.2(7) . . . . ? C34 C35 C36 C39 -174.6(4) . . . 1_655 ? C35 C36 C37 C38 -0.9(7) . . . . ? C39 C36 C37 C38 175.0(4) 1_655 . . . ? C36 C37 C38 N4 -0.3(7) . . . . ? N8 C40 C41 O8 -15.2(6) . . . . ? C43 C40 C41 O8 107.0(5) . . . . ? N8 C40 C41 O7 165.0(4) . . . . ? C43 C40 C41 O7 -72.8(6) . . . . ? N8 C40 C43 C42 -156.5(4) . . . . ? C41 C40 C43 C42 83.6(5) . . . . ? N8 C40 C43 C44 77.1(5) . . . . ? C41 C40 C43 C44 -42.8(6) . . . . ? C2 C1 N1 C5 -2.8(6) . . . . ? C2 C1 N1 Zn1 164.1(3) . . . . ? C4 C5 N1 C1 4.9(7) . . . . ? C4 C5 N1 Zn1 -162.5(4) . . . . ? C15 C16 N2 C12 5.2(7) . . . . ? C15 C16 N2 Zn1 -159.9(4) . . . . ? C13 C12 N2 C16 -4.8(7) . . . . ? C13 C12 N2 Zn1 161.3(4) . . . . ? C26 C27 N3 C23 3.3(7) . . . . ? C26 C27 N3 Zn2 -171.5(4) . . . . ? C24 C23 N3 C27 -3.2(7) . . . . ? C24 C23 N3 Zn2 171.6(3) . . . . ? C37 C38 N4 C34 1.3(7) . . . . ? C37 C38 N4 Zn2 -174.5(4) . . . . ? C35 C34 N4 C38 -1.0(7) . . . . ? C35 C34 N4 Zn2 174.9(4) . . . . ? C8 C7 N5 C6 -68.1(5) . . . . ? C9 C7 N5 C6 167.2(4) . . . . ? C3 C6 N5 C7 163.5(4) 1_455 . . . ? C14 C17 N6 C18 -57.1(5) 2_646 . . . ? C14 C17 N6 Zn1 176.6(3) 2_646 . . . ? C19 C18 N6 C17 -110.6(4) . . . . ? C20 C18 N6 C17 128.6(5) . . . . ? C19 C18 N6 Zn1 14.5(5) . . . . ? C20 C18 N6 Zn1 -106.3(4) . . . . ? C25 C28 N7 C29 -64.7(5) 2_545 . . . ? C25 C28 N7 Zn2 169.7(3) 2_545 . . . ? C31 C29 N7 C28 128.2(4) . . . . ? C30 C29 N7 C28 -109.8(4) . . . . ? C31 C29 N7 Zn2 -108.5(3) . . . . ? C30 C29 N7 Zn2 13.5(4) . . . . ? C36 C39 N8 C40 164.4(4) 1_455 . . . ? C41 C40 N8 C39 -86.7(5) . . . . ? C43 C40 N8 C39 149.5(4) . . . . ? O2 C8 O1 Zn1 17.2(7) . . . . ? C7 C8 O1 Zn1 -162.0(3) . . . . ? O4 C19 O3 Zn1 -176.3(4) . . . . ? C18 C19 O3 Zn1 6.8(5) . . . . ? O6 C30 O5 Zn2 -178.7(3) . . . . ? C29 C30 O5 Zn2 3.4(5) . . . . ? O8 C41 O7 Zn2 14.1(7) . . . . ? C40 C41 O7 Zn2 -166.2(3) . . . . ? C8 O1 Zn1 N1 -165.8(4) . . . . ? C8 O1 Zn1 O3 -62(2) . . . . ? C8 O1 Zn1 N2 83.1(4) . . . . ? C8 O1 Zn1 N6 -43.1(4) . . . . ? C1 N1 Zn1 O1 137.6(4) . . . . ? C5 N1 Zn1 O1 -55.6(3) . . . . ? C1 N1 Zn1 O3 -39.2(4) . . . . ? C5 N1 Zn1 O3 127.6(3) . . . . ? C1 N1 Zn1 N2 -133.9(3) . . . . ? C5 N1 Zn1 N2 32.9(4) . . . . ? C1 N1 Zn1 N6 38.9(4) . . . . ? C5 N1 Zn1 N6 -154.3(3) . . . . ? C19 O3 Zn1 O1 21(2) . . . . ? C19 O3 Zn1 N1 124.4(3) . . . . ? C19 O3 Zn1 N2 -124.4(3) . . . . ? C19 O3 Zn1 N6 1.5(3) . . . . ? C16 N2 Zn1 O1 108.1(4) . . . . ? C12 N2 Zn1 O1 -57.0(3) . . . . ? C16 N2 Zn1 N1 17.9(4) . . . . ? C12 N2 Zn1 N1 -147.2(3) . . . . ? C16 N2 Zn1 O3 -73.7(4) . . . . ? C12 N2 Zn1 O3 121.2(3) . . . . ? C16 N2 Zn1 N6 -154.5(3) . . . . ? C12 N2 Zn1 N6 40.4(4) . . . . ? C17 N6 Zn1 O1 -60.6(3) . . . . ? C18 N6 Zn1 O1 171.9(3) . . . . ? C17 N6 Zn1 N1 34.7(4) . . . . ? C18 N6 Zn1 N1 -92.8(3) . . . . ? C17 N6 Zn1 O3 118.3(3) . . . . ? C18 N6 Zn1 O3 -9.2(3) . . . . ? C17 N6 Zn1 N2 -153.7(3) . . . . ? C18 N6 Zn1 N2 78.9(3) . . . . ? C27 N3 Zn2 N4 40.6(4) . . . . ? C23 N3 Zn2 N4 -134.1(3) . . . . ? C27 N3 Zn2 O5 -51.7(4) . . . . ? C23 N3 Zn2 O5 133.6(3) . . . . ? C27 N3 Zn2 N7 -133.2(4) . . . . ? C23 N3 Zn2 N7 52.1(4) . . . . ? C27 N3 Zn2 O7 131.8(4) . . . . ? C23 N3 Zn2 O7 -42.9(3) . . . . ? C38 N4 Zn2 N3 45.0(4) . . . . ? C34 N4 Zn2 N3 -130.8(3) . . . . ? C38 N4 Zn2 O5 139.0(4) . . . . ? C34 N4 Zn2 O5 -36.8(4) . . . . ? C38 N4 Zn2 N7 -141.3(3) . . . . ? C34 N4 Zn2 N7 42.9(4) . . . . ? C38 N4 Zn2 O7 -46.3(4) . . . . ? C34 N4 Zn2 O7 137.9(4) . . . . ? C30 O5 Zn2 N3 -117.4(3) . . . . ? C30 O5 Zn2 N4 125.5(3) . . . . ? C30 O5 Zn2 N7 3.6(3) . . . . ? C30 O5 Zn2 O7 23.2(13) . . . . ? C28 N7 Zn2 N3 -154.1(3) . . . . ? C29 N7 Zn2 N3 78.8(3) . . . . ? C28 N7 Zn2 N4 32.5(3) . . . . ? C29 N7 Zn2 N4 -94.7(3) . . . . ? C28 N7 Zn2 O5 117.5(3) . . . . ? C29 N7 Zn2 O5 -9.7(3) . . . . ? C28 N7 Zn2 O7 -60.7(3) . . . . ? C29 N7 Zn2 O7 172.1(3) . . . . ? C41 O7 Zn2 N3 77.4(4) . . . . ? C41 O7 Zn2 N4 -165.5(4) . . . . ? C41 O7 Zn2 O5 -63.2(13) . . . . ? C41 O7 Zn2 N7 -43.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.860 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.733 _refine_diff_density_min -1.015 _refine_diff_density_rms 0.096 # Attachment 'combined cif.txt'