# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jian Zhang' _publ_contact_author_email zhj@fjirsm.ac.cn loop_ _publ_author_name 'Jian Zhang' 'Fei Wang' 'Hui Yang' 'Yao Kang' data_2 _database_code_depnum_ccdc_archive 'CCDC 892013' #TrackingRef '- check.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 N8 O3 Zn' _chemical_formula_sum 'C14 H14 N8 O3 Zn' _chemical_formula_weight 407.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 18.6244(4) _cell_length_b 10.2696(3) _cell_length_c 8.7992(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1682.98(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1716 _cell_measurement_theta_min 2.3099 _cell_measurement_theta_max 28.9728 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.609 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 1.494 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7544 _exptl_absorpt_correction_T_max 0.7544 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2083 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3757 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2434 _reflns_number_gt 2293 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+0.2966P] 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 -0.016(16) _refine_ls_number_reflns 2434 _refine_ls_number_parameters 235 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0304 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.0698 _refine_ls_wR_factor_gt 0.0679 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.400826(16) -0.02643(3) -0.13311(6) 0.01875(11) Uani 1 1 d . . . C5 C 0.4995(2) 0.0264(4) -0.3781(5) 0.0235(10) Uani 1 1 d . . . H5A H 0.5280 -0.0371 -0.3328 0.028 Uiso 1 1 calc R . . N1 N 0.51705(14) 0.0818(3) -0.5102(3) 0.0226(6) Uani 1 1 d . . . N4 N 0.45575(14) 0.2453(3) -0.6607(4) 0.0290(8) Uani 1 1 d . . . C4 C 0.39607(18) 0.3166(4) -0.6532(6) 0.0351(10) Uani 1 1 d . . . H4B H 0.3879 0.3710 -0.7359 0.042 Uiso 1 1 calc R . . N2 N 0.43857(14) 0.0680(3) -0.3155(3) 0.0229(6) Uani 1 1 d . . . C3 C 0.35322(17) 0.2424(4) -0.4234(4) 0.0268(8) Uani 1 1 d . . . N3 N 0.34628(15) 0.3213(3) -0.5444(4) 0.0338(7) Uani 1 1 d . . . C2 C 0.41368(17) 0.1601(4) -0.4190(4) 0.0205(7) Uani 1 1 d . . . C1 C 0.46219(16) 0.1674(3) -0.5380(4) 0.0218(7) Uani 1 1 d . . . N5 N 0.30240(16) 0.2450(3) -0.3159(4) 0.0373(8) Uani 1 1 d . . . H5B H 0.2662 0.2965 -0.3251 0.045 Uiso 1 1 calc R . . H5C H 0.3059 0.1952 -0.2377 0.045 Uiso 1 1 calc R . . O2 O 0.33923(12) 0.0981(3) -0.0327(3) 0.0330(6) Uani 1 1 d . . . N6 N 0.16297(14) 0.3335(3) 0.2806(3) 0.0253(7) Uani 1 1 d . . . O1 O 0.31494(14) -0.0514(3) 0.1430(3) 0.0369(7) Uani 1 1 d . . . C6 C 0.30689(19) 0.0558(4) 0.0866(4) 0.0266(8) Uani 1 1 d . . . C11 C 0.25906(19) 0.2829(4) 0.1139(4) 0.0295(9) Uani 1 1 d . . . H11A H 0.2924 0.3109 0.0424 0.035 Uiso 1 1 calc R . . C7 C 0.25562(18) 0.1530(4) 0.1552(4) 0.0246(8) Uani 1 1 d . . . C10 C 0.21234(19) 0.3700(4) 0.1801(5) 0.0314(9) Uani 1 1 d . . . H10A H 0.2154 0.4575 0.1536 0.038 Uiso 1 1 calc R . . C9 C 0.15930(19) 0.2073(4) 0.3218(4) 0.0345(10) Uani 1 1 d . . . H9A H 0.1251 0.1815 0.3928 0.041 Uiso 1 1 calc R . . C8 C 0.2049(2) 0.1161(4) 0.2615(5) 0.0337(9) Uani 1 1 d . . . H8A H 0.2017 0.0295 0.2919 0.040 Uiso 1 1 calc R . . O3 O 0.0855(2) -0.0477(4) 0.4800(5) 0.0788(13) Uani 1 1 d . . . N8 N 0.0027(3) -0.0968(5) 0.2942(5) 0.0660(14) Uani 1 1 d . . . H8B H 0.0234 -0.0587 0.2191 0.079 Uiso 1 1 calc R . . N7 N -0.0146(2) -0.1735(5) 0.5204(5) 0.0714(14) Uani 1 1 d . . . H7A H -0.0098 -0.1835 0.6169 0.086 Uiso 1 1 calc R . . C12 C -0.0712(3) -0.2321(6) 0.4348(6) 0.0650(16) Uani 1 1 d . . . H12A H -0.1176 -0.2165 0.4815 0.078 Uiso 1 1 calc R . . H12B H -0.0639 -0.3252 0.4241 0.078 Uiso 1 1 calc R . . C14 C 0.0307(3) -0.1006(6) 0.4354(6) 0.0534(13) Uani 1 1 d . . . C13 C -0.0649(3) -0.1625(6) 0.2814(6) 0.0650(16) Uani 1 1 d . . . H13A H -0.0646 -0.2242 0.1980 0.078 Uiso 1 1 calc R . . H13B H -0.1039 -0.1011 0.2669 0.078 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01748(17) 0.0209(2) 0.01784(17) -0.0015(3) -0.0006(2) 0.00096(14) C5 0.0223(14) 0.026(3) 0.0225(16) 0.0034(18) 0.0032(13) 0.0093(17) N1 0.0235(14) 0.0246(16) 0.0196(15) 0.0045(13) 0.0034(12) -0.0002(13) N4 0.0289(14) 0.0300(16) 0.028(2) 0.0078(15) -0.0005(13) 0.0023(13) C4 0.0392(19) 0.034(2) 0.032(3) 0.012(2) -0.0019(18) 0.0030(17) N2 0.0231(14) 0.0242(16) 0.0213(14) 0.0050(13) 0.0041(12) 0.0052(13) C3 0.0239(18) 0.027(2) 0.029(2) -0.0044(17) -0.0012(15) 0.0029(17) N3 0.0324(16) 0.0329(18) 0.0360(18) 0.0089(16) 0.0024(15) 0.0099(15) C2 0.0212(16) 0.0202(18) 0.0200(16) 0.0000(15) 0.0002(14) 0.0001(15) C1 0.0216(15) 0.0215(18) 0.0224(17) -0.0015(15) 0.0005(14) -0.0001(15) N5 0.0301(16) 0.047(2) 0.0352(18) 0.0085(17) 0.0086(15) 0.0189(16) O2 0.0373(14) 0.0316(15) 0.0301(14) 0.0008(13) 0.0133(12) 0.0058(13) N6 0.0228(14) 0.0254(17) 0.0276(16) -0.0029(14) 0.0050(13) 0.0054(13) O1 0.0353(14) 0.0255(15) 0.0497(18) 0.0056(14) 0.0117(13) 0.0050(13) C6 0.0209(17) 0.027(2) 0.032(2) -0.0039(17) 0.0006(16) 0.0010(17) C11 0.0264(18) 0.028(2) 0.034(2) 0.0014(18) 0.0100(16) 0.0004(17) C7 0.0248(17) 0.023(2) 0.0265(19) -0.0015(16) 0.0045(15) 0.0050(15) C10 0.037(2) 0.024(2) 0.034(2) 0.0033(18) 0.0102(18) 0.0022(17) C9 0.0351(19) 0.032(2) 0.036(2) 0.0035(17) 0.0173(16) 0.0028(17) C8 0.039(2) 0.022(2) 0.040(2) 0.0055(18) 0.0162(19) 0.0031(18) O3 0.088(3) 0.070(3) 0.078(3) 0.024(2) -0.006(2) -0.025(2) N8 0.098(4) 0.062(3) 0.038(2) 0.015(2) 0.014(2) -0.006(3) N7 0.072(3) 0.100(4) 0.042(2) 0.029(3) -0.008(2) -0.030(3) C12 0.061(3) 0.082(4) 0.053(3) 0.007(3) 0.000(3) -0.006(3) C14 0.067(3) 0.047(3) 0.047(3) 0.018(3) 0.005(3) 0.008(3) C13 0.097(4) 0.051(4) 0.047(3) -0.002(3) -0.015(3) 0.014(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 1.932(2) . ? Zn1 N1 1.957(3) 2_655 ? Zn1 N2 2.002(3) . ? Zn1 N6 2.015(3) 4_544 ? C5 N1 1.335(5) . ? C5 N2 1.333(5) . ? C5 H5A 0.9300 . ? N1 C1 1.369(4) . ? N1 Zn1 1.957(3) 2_654 ? N4 C4 1.333(4) . ? N4 C1 1.349(4) . ? C4 N3 1.334(5) . ? C4 H4B 0.9300 . ? N2 C2 1.392(4) . ? C3 N5 1.338(5) . ? C3 N3 1.344(5) . ? C3 C2 1.409(5) . ? C2 C1 1.385(5) . ? N5 H5B 0.8600 . ? N5 H5C 0.8600 . ? O2 C6 1.287(5) . ? N6 C9 1.347(5) . ? N6 C10 1.329(5) . ? N6 Zn1 2.015(3) 4 ? O1 C6 1.217(4) . ? C6 C7 1.508(5) . ? C11 C10 1.377(5) . ? C11 C7 1.384(5) . ? C11 H11A 0.9300 . ? C7 C8 1.382(5) . ? C10 H10A 0.9300 . ? C9 C8 1.371(5) . ? C9 H9A 0.9300 . ? C8 H8A 0.9300 . ? O3 C14 1.221(6) . ? N8 C14 1.348(6) . ? N8 C13 1.432(8) . ? N8 H8B 0.8600 . ? N7 C14 1.353(6) . ? N7 C12 1.428(7) . ? N7 H7A 0.8600 . ? C12 C13 1.532(7) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 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 O2 Zn1 N1 113.82(12) . 2_655 ? O2 Zn1 N2 104.73(11) . . ? N1 Zn1 N2 108.00(11) 2_655 . ? O2 Zn1 N6 107.16(11) . 4_544 ? N1 Zn1 N6 117.48(12) 2_655 4_544 ? N2 Zn1 N6 104.53(12) . 4_544 ? N1 C5 N2 115.6(3) . . ? N1 C5 H5A 122.2 . . ? N2 C5 H5A 122.2 . . ? C5 N1 C1 104.3(3) . . ? C5 N1 Zn1 123.2(2) . 2_654 ? C1 N1 Zn1 132.1(2) . 2_654 ? C4 N4 C1 111.1(3) . . ? N4 C4 N3 129.4(4) . . ? N4 C4 H4B 115.3 . . ? N3 C4 H4B 115.3 . . ? C5 N2 C2 103.3(3) . . ? C5 N2 Zn1 118.4(3) . . ? C2 N2 Zn1 137.4(2) . . ? N5 C3 N3 118.7(3) . . ? N5 C3 C2 123.9(4) . . ? N3 C3 C2 117.4(3) . . ? C4 N3 C3 118.7(3) . . ? N2 C2 C1 108.3(3) . . ? N2 C2 C3 133.8(3) . . ? C1 C2 C3 117.9(3) . . ? N4 C1 N1 126.1(3) . . ? N4 C1 C2 125.4(3) . . ? N1 C1 C2 108.5(3) . . ? C3 N5 H5B 120.0 . . ? C3 N5 H5C 120.0 . . ? H5B N5 H5C 120.0 . . ? C6 O2 Zn1 115.3(2) . . ? C9 N6 C10 119.0(3) . . ? C9 N6 Zn1 123.7(2) . 4 ? C10 N6 Zn1 117.2(3) . 4 ? O1 C6 O2 125.5(3) . . ? O1 C6 C7 120.9(3) . . ? O2 C6 C7 113.5(3) . . ? C10 C11 C7 119.0(3) . . ? C10 C11 H11A 120.5 . . ? C7 C11 H11A 120.5 . . ? C11 C7 C8 118.3(3) . . ? C11 C7 C6 120.3(3) . . ? C8 C7 C6 121.5(3) . . ? N6 C10 C11 122.4(4) . . ? N6 C10 H10A 118.8 . . ? C11 C10 H10A 118.8 . . ? N6 C9 C8 121.4(3) . . ? N6 C9 H9A 119.3 . . ? C8 C9 H9A 119.3 . . ? C9 C8 C7 119.8(3) . . ? C9 C8 H8A 120.1 . . ? C7 C8 H8A 120.1 . . ? C14 N8 C13 113.5(5) . . ? C14 N8 H8B 123.3 . . ? C13 N8 H8B 123.3 . . ? C14 N7 C12 113.7(4) . . ? C14 N7 H7A 123.1 . . ? C12 N7 H7A 123.1 . . ? N7 C12 C13 102.2(5) . . ? N7 C12 H12A 111.3 . . ? C13 C12 H12A 111.3 . . ? N7 C12 H12B 111.3 . . ? C13 C12 H12B 111.3 . . ? H12A C12 H12B 109.2 . . ? O3 C14 N8 127.4(5) . . ? O3 C14 N7 126.1(5) . . ? N8 C14 N7 106.5(5) . . ? N8 C13 C12 102.6(4) . . ? N8 C13 H13A 111.2 . . ? C12 C13 H13A 111.2 . . ? N8 C13 H13B 111.2 . . ? C12 C13 H13B 111.2 . . ? H13A C13 H13B 109.2 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5B O1 0.86 2.19 3.046(4) 172.0 4_554 N5 H5C O2 0.86 2.15 2.992(4) 165.5 . N7 H7A N4 0.86 2.32 3.126(5) 156.4 4_546 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.221 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.053 data_3 _database_code_depnum_ccdc_archive 'CCDC 892014' #TrackingRef '- check.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H17 N7 O3 Zn' _chemical_formula_sum 'C15 H17 N7 O3 Zn' _chemical_formula_weight 408.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 18.6627(5) _cell_length_b 10.5533(4) _cell_length_c 8.9082(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1754.50(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1419 _cell_measurement_theta_min 2.5279 _cell_measurement_theta_max 29.0937 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 1.431 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7628 _exptl_absorpt_correction_T_max 0.7628 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2083 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2908 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2114 _reflns_number_gt 1890 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+5.2191P] 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 0.03(5) _refine_ls_number_reflns 2114 _refine_ls_number_parameters 205 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1453 _refine_ls_wR_factor_gt 0.1406 _refine_ls_goodness_of_fit_ref 1.233 _refine_ls_restrained_S_all 1.596 _refine_ls_shift/su_max 0.079 _refine_ls_shift/su_mean 0.007 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 0.60093(5) 1.01529(10) 1.1295(3) 0.0246(3) Uani 1 1 d . . . C5 C 0.4974(8) 0.9765(11) 1.3697(19) 0.029(3) Uani 1 1 d . . . H5A H 0.4700 1.0376 1.3212 0.035 Uiso 1 1 calc R . . N1 N 0.4782(5) 0.9251(9) 1.5039(11) 0.029(2) Uani 1 1 d . . . N4 N 0.5361(5) 0.7688(9) 1.6567(13) 0.040(3) Uani 1 1 d . . . C4 C 0.5948(6) 0.6941(11) 1.6564(18) 0.044(4) Uani 1 1 d . . . H4B H 0.6004 0.6413 1.7392 0.052 Uiso 1 1 calc R . . N2 N 0.5593(5) 0.9316(9) 1.3127(12) 0.030(2) Uani 1 1 d . . . C3 C 0.6402(6) 0.7609(11) 1.4348(17) 0.036(3) Uani 1 1 d . . . N3 N 0.6438(5) 0.6872(10) 1.5559(12) 0.038(2) Uani 1 1 d . . . C2 C 0.5812(6) 0.8431(10) 1.4204(14) 0.028(3) Uani 1 1 d . . . C1 C 0.5323(6) 0.8402(10) 1.5332(13) 0.027(2) Uani 1 1 d . . . N5 N 0.6932(5) 0.7510(11) 1.3291(14) 0.050(3) Uani 1 1 d . . . H5B H 0.7277 0.6981 1.3418 0.060 Uiso 1 1 calc R . . H5C H 0.6919 0.7978 1.2501 0.060 Uiso 1 1 calc R . . O2 O 0.6613(4) 0.8848(8) 1.0368(10) 0.037(2) Uani 1 1 d . . . N6 N 0.8341(5) 0.6497(9) 0.7200(12) 0.032(2) Uani 1 1 d . . . O1 O 0.6940(5) 1.0332(8) 0.8729(12) 0.049(3) Uani 1 1 d . . . C6 C 0.6957(6) 0.9247(11) 0.9224(14) 0.029(3) Uani 1 1 d . . . C11 C 0.7430(6) 0.7020(11) 0.8952(14) 0.036(3) Uani 1 1 d . . . H11A H 0.7130 0.6761 0.9729 0.043 Uiso 1 1 calc R . . C7 C 0.7440(6) 0.8275(11) 0.8457(15) 0.032(3) Uani 1 1 d . . . C10 C 0.7889(7) 0.6167(12) 0.8228(18) 0.044(3) Uani 1 1 d . . . H10A H 0.7868 0.5317 0.8502 0.053 Uiso 1 1 calc R . . C9 C 0.8338(6) 0.7698(12) 0.6713(16) 0.046(4) Uani 1 1 d . . . H9A H 0.8638 0.7928 0.5924 0.056 Uiso 1 1 calc R . . C8 C 0.7896(6) 0.8612(12) 0.7366(16) 0.041(3) Uani 1 1 d . . . H8A H 0.7917 0.9450 0.7044 0.050 Uiso 1 1 calc R . . O3 O 0.9389(10) 0.914(2) 0.380(3) 0.150(7) Uiso 1 1 d D . . C15 C 1.0463(12) 0.956(2) 0.213(3) 0.134(10) Uiso 1 1 d D . . H15A H 1.0341 0.9909 0.3098 0.201 Uiso 1 1 calc RD . . H15B H 1.0516 1.0240 0.1422 0.201 Uiso 1 1 calc R . . H15C H 1.0905 0.9103 0.2209 0.201 Uiso 1 1 calc R . . N7 N 0.9854(12) 0.865(2) 0.160(3) 0.198(11) Uiso 1 1 d D . . C13 C 0.8468(15) 0.793(4) 0.263(4) 0.27(2) Uiso 1 1 d D . . H13A H 0.8216 0.8156 0.3531 0.403 Uiso 1 1 calc R . . H13B H 0.8530 0.7026 0.2596 0.403 Uiso 1 1 calc R . . H13C H 0.8198 0.8200 0.1772 0.403 Uiso 1 1 calc R . . C14 C 0.9710(14) 0.779(3) 0.022(3) 0.199(15) Uiso 1 1 d D . . H14A H 0.9247 0.7401 0.0315 0.298 Uiso 1 1 calc R . . H14B H 1.0072 0.7146 0.0161 0.298 Uiso 1 1 calc R . . H14C H 0.9721 0.8295 -0.0679 0.298 Uiso 1 1 calc RD . . C12 C 0.9209(14) 0.858(2) 0.262(3) 0.169(13) Uiso 1 1 d 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 0.0191(5) 0.0334(6) 0.0214(6) -0.0020(10) -0.0010(8) 0.0013(4) C5 0.025(5) 0.040(8) 0.022(7) -0.003(7) 0.003(5) 0.004(6) N1 0.028(5) 0.033(5) 0.026(5) 0.005(4) 0.007(4) 0.009(4) N4 0.042(5) 0.042(5) 0.035(7) 0.011(5) -0.005(5) -0.003(4) C4 0.050(7) 0.043(6) 0.038(10) 0.015(7) 0.002(7) 0.010(5) N2 0.025(5) 0.036(5) 0.030(6) -0.001(5) 0.006(4) 0.006(4) C3 0.024(6) 0.035(7) 0.051(8) -0.009(6) -0.006(6) 0.004(5) N3 0.032(5) 0.047(6) 0.034(6) 0.015(5) 0.003(5) 0.018(5) C2 0.025(5) 0.026(6) 0.033(7) 0.000(5) 0.000(5) 0.002(4) C1 0.027(6) 0.032(6) 0.022(6) -0.004(5) 0.003(5) -0.005(5) N5 0.038(6) 0.069(8) 0.044(7) 0.016(6) 0.015(5) 0.024(5) O2 0.029(4) 0.047(5) 0.036(5) -0.003(4) 0.012(4) 0.009(4) N6 0.028(5) 0.035(5) 0.032(6) -0.003(5) 0.009(5) 0.002(4) O1 0.052(6) 0.036(5) 0.059(7) 0.011(5) 0.015(5) 0.015(4) C6 0.025(6) 0.036(7) 0.027(6) -0.001(6) 0.001(5) 0.004(5) C11 0.037(7) 0.037(7) 0.035(8) 0.004(6) 0.025(6) 0.003(5) C7 0.025(6) 0.036(7) 0.035(7) -0.003(6) -0.001(5) 0.005(5) C10 0.041(7) 0.038(7) 0.052(9) 0.000(7) 0.006(7) 0.006(6) C9 0.039(6) 0.048(7) 0.052(11) 0.004(7) 0.018(6) 0.000(5) C8 0.041(7) 0.033(6) 0.050(8) 0.000(6) 0.011(7) 0.000(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 Zn1 N1 1.956(9) 2_674 ? Zn1 O2 1.961(8) . ? Zn1 N2 2.012(10) . ? Zn1 N6 2.033(9) 4_655 ? C5 N2 1.347(18) . ? C5 N1 1.361(19) . ? C5 H5A 0.9300 . ? N1 C1 1.375(14) . ? N1 Zn1 1.956(9) 2_675 ? N4 C4 1.351(14) . ? N4 C1 1.336(15) . ? C4 N3 1.282(16) . ? C4 H4B 0.9300 . ? N2 C2 1.400(15) . ? C3 N3 1.331(17) . ? C3 N5 1.368(16) . ? C3 C2 1.409(15) . ? C2 C1 1.357(15) . ? N5 H5B 0.8600 . ? N5 H5C 0.8600 . ? O2 C6 1.276(14) . ? N6 C10 1.293(17) . ? N6 C9 1.340(15) . ? N6 Zn1 2.033(9) 4_644 ? O1 C6 1.228(14) . ? C6 C7 1.527(16) . ? C11 C7 1.397(16) . ? C11 C10 1.401(17) . ? C11 H11A 0.9300 . ? C7 C8 1.339(17) . ? C10 H10A 0.9300 . ? C9 C8 1.397(17) . ? C9 H9A 0.9300 . ? C8 H8A 0.9300 . ? O3 C12 1.251(13) . ? C15 N7 1.564(12) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? N7 C12 1.509(13) . ? N7 C14 1.555(12) . ? C13 C12 1.544(13) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 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 N1 Zn1 O2 114.7(4) 2_674 . ? N1 Zn1 N2 108.3(4) 2_674 . ? O2 Zn1 N2 104.8(4) . . ? N1 Zn1 N6 116.9(4) 2_674 4_655 ? O2 Zn1 N6 108.3(3) . 4_655 ? N2 Zn1 N6 102.4(4) . 4_655 ? N2 C5 N1 114.7(12) . . ? N2 C5 H5A 122.7 . . ? N1 C5 H5A 122.7 . . ? C5 N1 C1 103.4(10) . . ? C5 N1 Zn1 125.0(8) . 2_675 ? C1 N1 Zn1 130.9(8) . 2_675 ? C4 N4 C1 111.7(11) . . ? N3 C4 N4 127.9(13) . . ? N3 C4 H4B 116.1 . . ? N4 C4 H4B 116.1 . . ? C5 N2 C2 103.1(11) . . ? C5 N2 Zn1 118.9(9) . . ? C2 N2 Zn1 137.4(7) . . ? N3 C3 N5 118.5(10) . . ? N3 C3 C2 118.2(12) . . ? N5 C3 C2 123.3(13) . . ? C4 N3 C3 119.8(10) . . ? C1 C2 N2 109.0(9) . . ? C1 C2 C3 116.4(12) . . ? N2 C2 C3 134.6(11) . . ? C2 C1 N4 126.0(10) . . ? C2 C1 N1 109.8(10) . . ? N4 C1 N1 124.2(10) . . ? C3 N5 H5B 120.0 . . ? C3 N5 H5C 120.0 . . ? H5B N5 H5C 120.0 . . ? C6 O2 Zn1 113.2(7) . . ? C10 N6 C9 118.8(11) . . ? C10 N6 Zn1 118.8(9) . 4_644 ? C9 N6 Zn1 122.2(8) . 4_644 ? O1 C6 O2 125.5(11) . . ? O1 C6 C7 118.8(11) . . ? O2 C6 C7 115.7(10) . . ? C7 C11 C10 117.1(10) . . ? C7 C11 H11A 121.5 . . ? C10 C11 H11A 121.5 . . ? C8 C7 C11 119.4(10) . . ? C8 C7 C6 121.4(11) . . ? C11 C7 C6 119.1(10) . . ? N6 C10 C11 123.5(12) . . ? N6 C10 H10A 118.2 . . ? C11 C10 H10A 118.2 . . ? N6 C9 C8 121.4(12) . . ? N6 C9 H9A 119.3 . . ? C8 C9 H9A 119.3 . . ? C7 C8 C9 119.6(12) . . ? C7 C8 H8A 120.2 . . ? C9 C8 H8A 120.2 . . ? N7 C15 H15A 109.4 . . ? N7 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N7 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 N7 C14 108(2) . . ? C12 N7 C15 115(2) . . ? C14 N7 C15 136.5(16) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.4 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.4 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N7 C14 H14A 109.5 . . ? N7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O3 C12 N7 105(2) . . ? O3 C12 C13 116(3) . . ? N7 C12 C13 138(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5B O1 0.86 2.29 3.142(14) 171.0 4_645 N5 H5C O2 0.86 2.19 3.022(15) 163.7 . _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 1.023 _refine_diff_density_min -0.550 _refine_diff_density_rms 0.111 data_4 _database_code_depnum_ccdc_archive 'CCDC 892015' #TrackingRef '- check.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H17 N7 O3 Zn' _chemical_formula_sum 'C16 H17 N7 O3 Zn' _chemical_formula_weight 420.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 18.4474(7) _cell_length_b 10.6981(6) _cell_length_c 8.9454(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1765.39(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1279 _cell_measurement_theta_min 2.5254 _cell_measurement_theta_max 29.1088 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 1.425 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7637 _exptl_absorpt_correction_T_max 0.7637 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2083 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3750 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0473 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2185 _reflns_number_gt 1879 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.6449P] 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(2) _refine_ls_number_reflns 2185 _refine_ls_number_parameters 209 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.39753(2) -0.01460(5) -0.13167(10) 0.02292(17) Uani 1 1 d . . . C5 C 0.5010(4) 0.0198(6) -0.3745(10) 0.0280(16) Uani 1 1 d . . . H5A H 0.5280 -0.0420 -0.3270 0.034 Uiso 1 1 calc R . . N1 N 0.5216(2) 0.0708(5) -0.5061(5) 0.0282(11) Uani 1 1 d . . . N4 N 0.4657(2) 0.2308(5) -0.6607(5) 0.0316(12) Uani 1 1 d . . . C4 C 0.4079(3) 0.3041(6) -0.6558(8) 0.0372(16) Uani 1 1 d . . . H4B H 0.4031 0.3586 -0.7362 0.045 Uiso 1 1 calc R . . N2 N 0.4394(2) 0.0643(5) -0.3176(5) 0.0250(11) Uani 1 1 d . . . C3 C 0.3590(3) 0.2380(6) -0.4331(7) 0.0294(14) Uani 1 1 d . . . N3 N 0.3550(2) 0.3121(5) -0.5527(6) 0.0370(13) Uani 1 1 d . . . C2 C 0.4184(3) 0.1536(6) -0.4220(6) 0.0254(13) Uani 1 1 d . . . C1 C 0.4684(2) 0.1564(5) -0.5357(7) 0.0258(13) Uani 1 1 d . . . N5 N 0.3064(2) 0.2476(6) -0.3301(6) 0.0440(15) Uani 1 1 d . . . H5B H 0.2717 0.3002 -0.3425 0.053 Uiso 1 1 calc R . . H5C H 0.3074 0.2011 -0.2517 0.053 Uiso 1 1 calc R . . O2 O 0.33892(18) 0.1164(4) -0.0386(5) 0.0339(10) Uani 1 1 d . . . N6 N 0.1713(2) 0.3547(5) 0.2885(6) 0.0287(11) Uani 1 1 d . . . O1 O 0.3081(2) -0.0274(4) 0.1288(5) 0.0457(12) Uani 1 1 d . . . C6 C 0.3052(3) 0.0777(6) 0.0793(7) 0.0280(14) Uani 1 1 d . . . C11 C 0.2619(3) 0.3001(6) 0.1114(7) 0.0355(16) Uani 1 1 d . . . H11A H 0.2938 0.3256 0.0368 0.043 Uiso 1 1 calc R . . C7 C 0.2594(3) 0.1778(6) 0.1525(6) 0.0265(13) Uani 1 1 d . . . C10 C 0.2176(3) 0.3861(6) 0.1795(7) 0.0367(15) Uani 1 1 d . . . H10A H 0.2198 0.4690 0.1488 0.044 Uiso 1 1 calc R . . C9 C 0.1705(3) 0.2359(6) 0.3342(6) 0.0345(16) Uani 1 1 d . . . H9A H 0.1397 0.2139 0.4123 0.041 Uiso 1 1 calc R . . C8 C 0.2129(3) 0.1449(6) 0.2710(7) 0.0357(14) Uani 1 1 d . . . H8A H 0.2111 0.0630 0.3058 0.043 Uiso 1 1 calc R . . N7 N 0.0125(3) 0.1136(6) -0.2028(8) 0.0621(16) Uiso 1 1 d . . . O3 O 0.0919(3) 0.0657(7) -0.3891(8) 0.096(2) Uiso 1 1 d . . . C13 C 0.1242(5) 0.2068(8) -0.1917(10) 0.077(3) Uiso 1 1 d . . . H13A H 0.1402 0.2755 -0.2544 0.093 Uiso 1 1 calc R . . H13B H 0.1664 0.1610 -0.1574 0.093 Uiso 1 1 calc R . . C14 C 0.0803(5) 0.2548(10) -0.0602(14) 0.102(3) Uiso 1 1 d . . . H14A H 0.0749 0.3449 -0.0652 0.123 Uiso 1 1 calc R . . H14B H 0.1034 0.2329 0.0336 0.123 Uiso 1 1 calc R . . C12 C 0.0745(4) 0.1241(8) -0.2740(9) 0.065(2) Uiso 1 1 d . . . C15 C 0.0068(4) 0.1899(9) -0.0753(10) 0.075(3) Uiso 1 1 d . . . H15A H -0.0034 0.1399 0.0127 0.089 Uiso 1 1 calc R . . H15B H -0.0316 0.2509 -0.0877 0.089 Uiso 1 1 calc R . . C16 C -0.0445(5) 0.0321(9) -0.2491(12) 0.090(3) Uiso 1 1 d . . . H16A H -0.0855 0.0427 -0.1842 0.135 Uiso 1 1 calc R . . H16B H -0.0281 -0.0529 -0.2443 0.135 Uiso 1 1 calc R . . H16C H -0.0582 0.0519 -0.3499 0.135 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0189(2) 0.0290(3) 0.0208(3) -0.0034(5) -0.0004(4) 0.0011(2) C5 0.024(2) 0.035(5) 0.025(3) 0.000(3) 0.001(2) 0.007(3) N1 0.024(2) 0.035(3) 0.025(3) 0.004(2) 0.001(2) 0.005(2) N4 0.034(2) 0.033(3) 0.028(3) 0.008(2) 0.003(2) -0.002(2) C4 0.046(3) 0.038(3) 0.027(4) 0.010(3) -0.002(3) 0.003(3) N2 0.020(2) 0.033(3) 0.021(2) 0.001(2) -0.0001(19) 0.000(2) C3 0.022(3) 0.034(4) 0.032(3) -0.003(3) -0.002(2) 0.004(3) N3 0.036(3) 0.037(3) 0.039(3) 0.005(3) 0.000(2) 0.009(2) C2 0.024(3) 0.028(3) 0.024(3) 0.000(3) -0.005(2) -0.003(2) C1 0.022(3) 0.026(3) 0.029(3) 0.000(3) -0.003(2) -0.003(2) N5 0.034(3) 0.054(4) 0.043(3) 0.009(3) 0.008(3) 0.020(3) O2 0.0341(18) 0.031(3) 0.037(2) 0.000(2) 0.0099(19) 0.0107(19) N6 0.026(2) 0.033(3) 0.027(3) -0.001(3) 0.005(2) -0.001(2) O1 0.052(3) 0.035(3) 0.050(3) 0.005(3) 0.015(2) 0.011(2) C6 0.023(3) 0.033(4) 0.028(3) -0.006(3) -0.003(2) -0.002(3) C11 0.030(3) 0.039(4) 0.038(4) 0.008(3) 0.018(3) 0.003(3) C7 0.025(3) 0.032(4) 0.023(3) 0.001(3) 0.005(2) 0.002(3) C10 0.039(3) 0.034(4) 0.037(4) 0.008(3) 0.008(3) 0.007(3) C9 0.033(3) 0.037(4) 0.034(4) -0.001(3) 0.016(3) -0.001(2) C8 0.039(3) 0.030(4) 0.038(4) 0.003(3) 0.006(3) 0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 1.956(4) . ? Zn1 N1 1.962(4) 2_655 ? Zn1 N6 2.020(5) 4_544 ? Zn1 N2 2.018(5) . ? C5 N2 1.334(9) . ? C5 N1 1.351(10) . ? C5 H5A 0.9300 . ? N1 C1 1.368(6) . ? N1 Zn1 1.962(4) 2_654 ? N4 C1 1.374(7) . ? N4 C4 1.325(7) . ? C4 N3 1.345(7) . ? C4 H4B 0.9300 . ? N2 C2 1.391(7) . ? C3 N3 1.333(7) . ? C3 C2 1.424(8) . ? C3 N5 1.341(7) . ? C2 C1 1.373(8) . ? N5 H5B 0.8600 . ? N5 H5C 0.8600 . ? O2 C6 1.293(7) . ? N6 C9 1.335(7) . ? N6 C10 1.338(7) . ? N6 Zn1 2.020(4) 4 ? O1 C6 1.210(7) . ? C6 C7 1.513(8) . ? C11 C7 1.360(8) . ? C11 C10 1.374(8) . ? C11 H11A 0.9300 . ? C7 C8 1.408(8) . ? C10 H10A 0.9300 . ? C9 C8 1.372(8) . ? C9 H9A 0.9300 . ? C8 H8A 0.9300 . ? N7 C15 1.407(10) . ? N7 C12 1.313(9) . ? N7 C16 1.427(10) . ? O3 C12 1.246(9) . ? C13 C12 1.472(12) . ? C13 C14 1.517(14) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.529(10) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Zn1 N1 113.34(19) . 2_655 ? O2 Zn1 N6 107.40(16) . 4_544 ? N1 Zn1 N6 118.0(2) 2_655 4_544 ? O2 Zn1 N2 105.23(19) . . ? N1 Zn1 N2 107.99(18) 2_655 . ? N6 Zn1 N2 103.8(2) 4_544 . ? N2 C5 N1 115.3(6) . . ? N2 C5 H5A 122.3 . . ? N1 C5 H5A 122.3 . . ? C1 N1 C5 103.7(5) . . ? C1 N1 Zn1 129.8(4) . 2_654 ? C5 N1 Zn1 126.1(4) . 2_654 ? C1 N4 C4 110.2(5) . . ? N3 C4 N4 130.1(6) . . ? N3 C4 H4B 115.0 . . ? N4 C4 H4B 115.0 . . ? C5 N2 C2 103.1(5) . . ? C5 N2 Zn1 119.5(5) . . ? C2 N2 Zn1 137.2(4) . . ? N3 C3 C2 118.3(5) . . ? N3 C3 N5 117.8(5) . . ? C2 C3 N5 123.9(6) . . ? C3 N3 C4 118.2(5) . . ? N2 C2 C3 134.2(5) . . ? N2 C2 C1 109.0(5) . . ? C3 C2 C1 116.9(5) . . ? N4 C1 N1 124.9(5) . . ? N4 C1 C2 126.3(5) . . ? N1 C1 C2 108.9(5) . . ? C3 N5 H5B 120.0 . . ? C3 N5 H5C 120.0 . . ? H5B N5 H5C 120.0 . . ? C6 O2 Zn1 112.6(4) . . ? C9 N6 C10 118.0(5) . . ? C9 N6 Zn1 122.9(4) . 4 ? C10 N6 Zn1 119.0(4) . 4 ? O2 C6 O1 125.1(6) . . ? O2 C6 C7 113.3(5) . . ? O1 C6 C7 121.6(5) . . ? C7 C11 C10 120.2(5) . . ? C7 C11 H11A 119.9 . . ? C10 C11 H11A 119.9 . . ? C8 C7 C11 117.7(5) . . ? C8 C7 C6 119.3(5) . . ? C11 C7 C6 123.0(5) . . ? N6 C10 C11 122.3(6) . . ? N6 C10 H10A 118.8 . . ? C11 C10 H10A 118.8 . . ? N6 C9 C8 122.9(5) . . ? N6 C9 H9A 118.6 . . ? C8 C9 H9A 118.6 . . ? C7 C8 C9 118.7(6) . . ? C7 C8 H8A 120.7 . . ? C9 C8 H8A 120.7 . . ? C15 N7 C12 114.1(7) . . ? C15 N7 C16 122.3(7) . . ? C12 N7 C16 123.6(8) . . ? C12 C13 C14 105.0(7) . . ? C12 C13 H13A 110.8 . . ? C14 C13 H13A 110.8 . . ? C12 C13 H13B 110.8 . . ? C14 C13 H13B 110.8 . . ? H13A C13 H13B 108.8 . . ? C13 C14 C15 104.6(9) . . ? C13 C14 H14A 110.8 . . ? C15 C14 H14A 110.8 . . ? C13 C14 H14B 110.8 . . ? C15 C14 H14B 110.8 . . ? H14A C14 H14B 108.9 . . ? O3 C12 N7 125.5(8) . . ? O3 C12 C13 123.7(8) . . ? N7 C12 C13 110.6(8) . . ? N7 C15 C14 105.6(7) . . ? N7 C15 H15A 110.6 . . ? C14 C15 H15A 110.6 . . ? N7 C15 H15B 110.6 . . ? C14 C15 H15B 110.6 . . ? H15A C15 H15B 108.8 . . ? N7 C16 H16A 109.5 . . ? N7 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N7 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5B O1 0.86 2.37 3.223(7) 169.9 4_554 N5 H5C O2 0.86 2.19 3.021(7) 162.8 . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.366 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.071