# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 N8 O4 Zn2' _chemical_formula_weight 461.02 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 Tetragonal _symmetry_space_group_name_H-M P4/nnc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y+1/2, x, z' 'y, -x+1/2, z' '-x+1/2, y, -z+1/2' 'x, -y+1/2, -z+1/2' 'y, x, -z+1/2' '-y+1/2, -x+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y-1/2, -x, -z' '-y, x-1/2, -z' 'x-1/2, -y, z-1/2' '-x, y-1/2, z-1/2' '-y, -x, z-1/2' 'y-1/2, x-1/2, z-1/2' _cell_length_a 12.6724(4) _cell_length_b 12.6724(4) _cell_length_c 25.2868(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4060.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5501 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 27.60 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 2.394 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6460 _exptl_absorpt_correction_T_max 0.6725 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 13894 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1802 _reflns_number_gt 1632 _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^)+(0.0454P)^2^+2.3721P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00079(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1802 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0869 _refine_ls_wR_factor_gt 0.0847 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.121 _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 -0.1077(3) 0.0707(3) 0.33891(13) 0.0477(8) Uani 1 1 d . . . C2 C -0.1818(3) 0.0725(3) 0.29283(12) 0.0473(8) Uani 1 1 d . . . C3 C -0.1431(3) 0.0739(4) 0.24227(14) 0.0691(12) Uani 1 1 d . . . H3 H -0.0706 0.0752 0.2366 0.083 Uiso 1 1 calc R . . C4 C -0.2889(3) 0.0734(4) 0.30028(13) 0.0709(13) Uani 1 1 d . . . H4 H -0.3160 0.0736 0.3345 0.085 Uiso 1 1 calc R . . C5 C 0.2307(2) -0.0402(2) 0.49868(10) 0.0365(7) Uani 1 1 d . . . H5 H 0.2699 -0.0601 0.5281 0.044 Uiso 1 1 calc R . . C6 C 0.1894(2) 0.0043(2) 0.42108(10) 0.0311(6) Uani 1 1 d . . . N1 N 0.10060(18) 0.00113(19) 0.44871(8) 0.0294(5) Uani 1 1 d . . . N2 N 0.12891(18) -0.02708(18) 0.49977(8) 0.0305(5) Uani 1 1 d . . . N3 N 0.27391(18) -0.0222(2) 0.45103(9) 0.0343(6) Uani 1 1 d . . . N4 N 0.1954(2) 0.0312(3) 0.36992(10) 0.0585(9) Uani 1 1 d . . . H4A H 0.1392 0.0479 0.3528 0.070 Uiso 1 1 calc R . . H4B H 0.2556 0.0317 0.3542 0.070 Uiso 1 1 calc R . . O1 O -0.1474(2) 0.0515(2) 0.38390(9) 0.0646(7) Uani 1 1 d . . . O2 O -0.01259(19) 0.08842(19) 0.33259(10) 0.0561(7) Uani 1 1 d . . . Zn1 Zn -0.03850(2) 0.06949(3) 0.437520(11) 0.02694(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.059(2) 0.0468(19) 0.0375(19) -0.0027(14) -0.0219(17) 0.0020(16) C2 0.0414(18) 0.072(2) 0.0285(16) -0.0006(15) -0.0120(14) 0.0008(15) C3 0.0360(18) 0.136(4) 0.0359(19) 0.005(2) -0.0075(15) -0.005(2) C4 0.048(2) 0.143(4) 0.0221(15) -0.003(2) -0.0041(15) 0.001(2) C5 0.0306(16) 0.0566(18) 0.0225(14) 0.0098(13) -0.0037(12) -0.0007(13) C6 0.0311(15) 0.0381(15) 0.0241(13) 0.0034(12) -0.0016(11) 0.0033(12) N1 0.0308(12) 0.0357(13) 0.0217(11) 0.0042(10) -0.0012(9) 0.0019(10) N2 0.0309(13) 0.0400(13) 0.0206(11) 0.0069(9) -0.0025(10) -0.0001(10) N3 0.0284(13) 0.0490(15) 0.0254(11) 0.0058(11) 0.0000(10) 0.0011(10) N4 0.0359(15) 0.112(3) 0.0280(13) 0.0225(15) 0.0029(11) 0.0159(16) O1 0.0721(18) 0.091(2) 0.0309(13) 0.0048(12) -0.0216(12) -0.0105(14) O2 0.0455(14) 0.0621(15) 0.0606(16) -0.0093(12) -0.0265(12) 0.0072(12) Zn1 0.0300(2) 0.0318(2) 0.0190(2) 0.00237(12) -0.00194(12) 0.00184(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.236(4) . ? C1 O1 1.268(4) . ? C1 C2 1.497(4) . ? C2 C3 1.370(5) . ? C2 C4 1.370(5) . ? C3 C4 1.379(5) 5_455 ? C3 H3 0.9300 . ? C4 C3 1.379(5) 5_455 ? C4 H4 0.9300 . ? C5 N2 1.301(3) . ? C5 N3 1.343(3) . ? C5 H5 0.9300 . ? C6 N1 1.325(4) . ? C6 N4 1.340(4) . ? C6 N3 1.354(3) . ? N1 N2 1.387(3) . ? N1 Zn1 1.984(2) . ? N2 Zn1 2.029(2) 9_556 ? N3 Zn1 2.024(2) 3 ? N4 H4A 0.8600 . ? N4 H4B 0.8600 . ? O1 Zn1 1.948(2) . ? Zn1 N3 2.024(2) 4 ? Zn1 N2 2.029(2) 9_556 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 122.5(3) . . ? O2 C1 C2 120.5(3) . . ? O1 C1 C2 116.9(3) . . ? C3 C2 C4 118.9(3) . . ? C3 C2 C1 120.1(3) . . ? C4 C2 C1 121.0(3) . . ? C2 C3 C4 120.3(3) . 5_455 ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 5_455 . ? C2 C4 C3 120.8(3) . 5_455 ? C2 C4 H4 119.6 . . ? C3 C4 H4 119.6 5_455 . ? N2 C5 N3 113.7(2) . . ? N2 C5 H5 123.2 . . ? N3 C5 H5 123.2 . . ? N1 C6 N4 124.4(3) . . ? N1 C6 N3 111.7(2) . . ? N4 C6 N3 123.9(3) . . ? C6 N1 N2 106.2(2) . . ? C6 N1 Zn1 131.75(18) . . ? N2 N1 Zn1 118.36(17) . . ? C5 N2 N1 105.6(2) . . ? C5 N2 Zn1 122.87(18) . 9_556 ? N1 N2 Zn1 130.53(17) . 9_556 ? C5 N3 C6 102.8(2) . . ? C5 N3 Zn1 122.28(18) . 3 ? C6 N3 Zn1 134.95(19) . 3 ? C6 N4 H4A 120.0 . . ? C6 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C1 O1 Zn1 108.7(2) . . ? O1 Zn1 N1 132.64(11) . . ? O1 Zn1 N3 107.72(11) . 4 ? N1 Zn1 N3 108.27(10) . 4 ? O1 Zn1 N2 96.48(10) . 9_556 ? N1 Zn1 N2 105.94(9) . 9_556 ? N3 Zn1 N2 100.68(9) 4 9_556 ? 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 O2 C1 C2 C3 12.4(5) . . . . ? O1 C1 C2 C3 -168.4(4) . . . . ? O2 C1 C2 C4 -167.2(4) . . . . ? O1 C1 C2 C4 12.0(5) . . . . ? C4 C2 C3 C4 -1.7(6) . . . 5_455 ? C1 C2 C3 C4 178.7(4) . . . 5_455 ? C3 C2 C4 C3 1.1(6) . . . 5_455 ? C1 C2 C4 C3 -179.3(4) . . . 5_455 ? N4 C6 N1 N2 -178.3(3) . . . . ? N3 C6 N1 N2 1.2(3) . . . . ? N4 C6 N1 Zn1 -21.0(5) . . . . ? N3 C6 N1 Zn1 158.5(2) . . . . ? N3 C5 N2 N1 0.5(3) . . . . ? N3 C5 N2 Zn1 170.40(19) . . . 9_556 ? C6 N1 N2 C5 -1.0(3) . . . . ? Zn1 N1 N2 C5 -161.90(19) . . . . ? C6 N1 N2 Zn1 -169.8(2) . . . 9_556 ? Zn1 N1 N2 Zn1 29.3(3) . . . 9_556 ? N2 C5 N3 C6 0.2(3) . . . . ? N2 C5 N3 Zn1 -179.18(19) . . . 3 ? N1 C6 N3 C5 -0.8(3) . . . . ? N4 C6 N3 C5 178.7(3) . . . . ? N1 C6 N3 Zn1 178.4(2) . . . 3 ? N4 C6 N3 Zn1 -2.1(5) . . . 3 ? O2 C1 O1 Zn1 5.6(4) . . . . ? C2 C1 O1 Zn1 -173.6(2) . . . . ? C1 O1 Zn1 N1 -59.0(3) . . . . ? C1 O1 Zn1 N3 78.8(2) . . . 4 ? C1 O1 Zn1 N2 -177.8(2) . . . 9_556 ? C6 N1 Zn1 O1 67.2(3) . . . . ? N2 N1 Zn1 O1 -137.75(19) . . . . ? C6 N1 Zn1 N3 -70.6(3) . . . 4 ? N2 N1 Zn1 N3 84.5(2) . . . 4 ? C6 N1 Zn1 N2 -177.8(3) . . . 9_556 ? N2 N1 Zn1 N2 -22.8(2) . . . 9_556 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.413 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.098 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.250 0.250 0.250 484 107 ' ' 2 0.250 0.750 0.093 19 1 ' ' 3 0.250 0.750 0.593 19 2 ' ' 4 0.250 0.750 0.906 19 2 ' ' 5 0.250 0.750 0.406 19 2 ' ' 6 0.750 0.750 0.745 484 107 ' ' 7 0.750 0.250 0.406 19 2 ' ' 8 0.750 0.250 0.907 19 2 ' ' 9 0.750 0.250 0.093 19 2 ' ' 10 0.750 0.250 0.593 19 1 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 942583' ####################################################################### # # 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_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H5 N4 O2 Zn' _chemical_formula_weight 230.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 P-31c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, -z+1/2' 'x, x-y, -z+1/2' '-x+y, y, -z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'y, x, z-1/2' '-x, -x+y, z-1/2' 'x-y, -y, z-1/2' _cell_length_a 11.8739(15) _cell_length_b 11.8739(15) _cell_length_c 25.494(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3112.8(8) _cell_formula_units_Z 12 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3318 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 26.83 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1380 _exptl_absorpt_coefficient_mu 2.342 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5921 _exptl_absorpt_correction_T_max 0.7057 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 13911 _diffrn_reflns_av_R_equivalents 0.0880 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1839 _reflns_number_gt 1405 _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^)+(0.0515P)^2^+26.7035P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1839 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0999 _refine_ls_R_factor_gt 0.0827 _refine_ls_wR_factor_ref 0.1977 _refine_ls_wR_factor_gt 0.1860 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 0.4071(12) 0.3489(11) 0.1599(3) 0.075(3) Uani 1 1 d . . . C2 C 0.4026(12) 0.2696(10) 0.2060(3) 0.072(3) Uani 1 1 d . . . C3 C 0.3997(15) 0.3135(12) 0.2563(3) 0.092(4) Uani 1 1 d . . . H3 H 0.3983 0.3906 0.2607 0.110 Uiso 1 1 calc R . . C4 C 0.1655(8) 0.4476(9) 0.0799(3) 0.055(2) Uani 1 1 d . . . C5 C 0.1929(10) 0.4130(12) 0.0018(3) 0.073(3) Uani 1 1 d . . . H5 H 0.2247 0.3935 -0.0281 0.088 Uiso 1 1 calc R . . C6 C 0.3987(13) 0.1553(10) 0.2002(3) 0.082(4) Uani 1 1 d . . . H6 H 0.3954 0.1225 0.1667 0.098 Uiso 1 1 calc R . . N1 N 0.5399(8) 0.6163(8) 0.0531(2) 0.061(2) Uani 1 1 d . . . N2 N 0.2423(9) 0.4195(9) 0.0504(2) 0.072(2) Uani 1 1 d . . . N3 N 0.1766(10) 0.4605(11) 0.1331(3) 0.078(3) Uani 1 1 d . . . N4 N 0.0967(7) 0.4366(9) 0.0007(2) 0.070(2) Uani 1 1 d . . . O1 O 0.4127(9) 0.3073(8) 0.1144(2) 0.089(2) Uani 1 1 d . . . O2 O 0.4031(8) 0.4504(8) 0.1658(3) 0.080(2) Uani 1 1 d . . . Zn1 Zn 0.41315(13) 0.42694(12) 0.06271(3) 0.0619(5) Uani 1 1 d . . . H1M H 0.244(8) 0.466(7) 0.146(3) 0.04(2) Uiso 1 1 d . . . H2M H 0.131(11) 0.497(10) 0.154(4) 0.09(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.128(10) 0.086(7) 0.039(4) 0.015(5) -0.006(5) 0.075(8) C2 0.137(10) 0.075(7) 0.029(4) 0.007(4) -0.005(5) 0.071(7) C3 0.186(13) 0.111(9) 0.039(4) 0.010(5) 0.002(6) 0.120(10) C4 0.045(5) 0.080(7) 0.037(4) 0.008(4) 0.007(4) 0.028(5) C5 0.083(7) 0.137(10) 0.023(4) 0.000(5) 0.000(4) 0.073(7) C6 0.165(12) 0.061(6) 0.028(4) 0.004(4) 0.003(5) 0.063(7) N1 0.108(6) 0.086(6) 0.023(3) 0.004(3) 0.006(3) 0.074(5) N2 0.094(6) 0.127(7) 0.030(3) 0.001(4) 0.005(4) 0.083(6) N3 0.088(7) 0.145(9) 0.027(3) -0.006(4) -0.008(4) 0.079(7) N4 0.056(5) 0.128(8) 0.026(3) -0.003(4) 0.004(3) 0.046(5) O1 0.152(8) 0.112(6) 0.032(3) 0.013(4) 0.003(4) 0.088(6) O2 0.118(6) 0.095(6) 0.058(4) 0.017(4) -0.012(4) 0.076(5) Zn1 0.1077(10) 0.0963(9) 0.0233(5) 0.0064(5) 0.0034(5) 0.0823(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.239(12) . ? C1 O1 1.275(11) . ? C1 C2 1.492(11) . ? C2 C6 1.343(13) . ? C2 C3 1.390(12) . ? C3 C6 1.384(12) 5 ? C3 H3 0.9300 . ? C4 N1 1.328(11) 3_565 ? C4 N2 1.347(11) . ? C4 N3 1.365(10) . ? C5 N4 1.305(12) . ? C5 N2 1.357(10) . ? C5 H5 0.9300 . ? C6 C3 1.384(12) 5 ? C6 H6 0.9300 . ? N1 C4 1.328(11) 2_665 ? N1 N4 1.409(8) 2_665 ? N1 Zn1 1.999(8) . ? N2 Zn1 2.010(8) . ? N3 H1M 0.84(8) . ? N3 H2M 1.01(11) . ? N4 N1 1.409(8) 3_565 ? N4 Zn1 2.012(7) 9 ? O1 Zn1 1.935(6) . ? Zn1 N4 2.012(7) 8 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 121.5(8) . . ? O2 C1 C2 120.7(9) . . ? O1 C1 C2 117.8(9) . . ? C6 C2 C3 119.1(8) . . ? C6 C2 C1 121.5(8) . . ? C3 C2 C1 119.4(9) . . ? C6 C3 C2 120.5(9) 5 . ? C6 C3 H3 119.7 5 . ? C2 C3 H3 119.7 . . ? N1 C4 N2 114.7(7) 3_565 . ? N1 C4 N3 122.4(8) 3_565 . ? N2 C4 N3 122.9(8) . . ? N4 C5 N2 114.1(8) . . ? N4 C5 H5 123.0 . . ? N2 C5 H5 123.0 . . ? C2 C6 C3 120.3(8) . 5 ? C2 C6 H6 119.9 . . ? C3 C6 H6 119.9 5 . ? C4 N1 N4 103.9(7) 2_665 2_665 ? C4 N1 Zn1 129.6(6) 2_665 . ? N4 N1 Zn1 115.5(6) 2_665 . ? C4 N2 C5 101.3(7) . . ? C4 N2 Zn1 134.1(6) . . ? C5 N2 Zn1 122.9(6) . . ? C4 N3 H1M 115(5) . . ? C4 N3 H2M 123(6) . . ? H1M N3 H2M 118(8) . . ? C5 N4 N1 106.1(7) . 3_565 ? C5 N4 Zn1 124.6(6) . 9 ? N1 N4 Zn1 128.6(6) 3_565 9 ? C1 O1 Zn1 108.5(6) . . ? O1 Zn1 N1 129.3(3) . . ? O1 Zn1 N2 116.2(4) . . ? N1 Zn1 N2 101.9(3) . . ? O1 Zn1 N4 96.9(3) . 8 ? N1 Zn1 N4 105.0(3) . 8 ? N2 Zn1 N4 104.3(3) . 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 O2 C1 C2 C6 175.8(12) . . . . ? O1 C1 C2 C6 -2.9(19) . . . . ? O2 C1 C2 C3 -2.9(19) . . . . ? O1 C1 C2 C3 178.4(12) . . . . ? C6 C2 C3 C6 2.9(19) . . . 5 ? C1 C2 C3 C6 -178.4(12) . . . 5 ? C3 C2 C6 C3 -3.8(18) . . . 5 ? C1 C2 C6 C3 177.5(13) . . . 5 ? N1 C4 N2 C5 -0.8(12) 3_565 . . . ? N3 C4 N2 C5 178.2(10) . . . . ? N1 C4 N2 Zn1 164.0(7) 3_565 . . . ? N3 C4 N2 Zn1 -16.9(16) . . . . ? N4 C5 N2 C4 0.9(13) . . . . ? N4 C5 N2 Zn1 -166.2(8) . . . . ? N2 C5 N4 N1 -0.7(13) . . . 3_565 ? N2 C5 N4 Zn1 -171.8(7) . . . 9 ? O2 C1 O1 Zn1 -0.1(15) . . . . ? C2 C1 O1 Zn1 178.6(9) . . . . ? C1 O1 Zn1 N1 59.9(9) . . . . ? C1 O1 Zn1 N2 -74.5(9) . . . . ? C1 O1 Zn1 N4 175.8(8) . . . 8 ? C4 N1 Zn1 O1 -77.5(8) 2_665 . . . ? N4 N1 Zn1 O1 144.8(6) 2_665 . . . ? C4 N1 Zn1 N2 61.5(8) 2_665 . . . ? N4 N1 Zn1 N2 -76.2(6) 2_665 . . . ? C4 N1 Zn1 N4 170.1(7) 2_665 . . 8 ? N4 N1 Zn1 N4 32.4(8) 2_665 . . 8 ? C4 N2 Zn1 O1 66.4(11) . . . . ? C5 N2 Zn1 O1 -131.4(9) . . . . ? C4 N2 Zn1 N1 -79.2(10) . . . . ? C5 N2 Zn1 N1 83.0(9) . . . . ? C4 N2 Zn1 N4 171.7(10) . . . 8 ? C5 N2 Zn1 N4 -26.1(10) . . . 8 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.537 _refine_diff_density_min -1.173 _refine_diff_density_rms 0.109 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.009 -0.007 -0.002 904 304 ' ' 2 0.333 0.666 0.893 26 4 ' ' 3 0.333 0.666 0.607 26 4 ' ' 4 0.333 0.666 0.750 9 1 ' ' 5 0.666 0.333 0.393 26 4 ' ' 6 0.666 0.333 0.107 26 4 ' ' 7 0.666 0.333 0.250 9 1 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 942584'