# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Ji-Qing Xu' _publ_contact_author_email XJQ@MAIL.JLU.EDU.CN _publ_section_title ; Fluorescent Metal-organic Polymers of Zinc and Cadmium from Hydrothermal in Situ Acylation Reaction ; loop_ _publ_author_name 'Ji-Qing Xu' 'Xiao-Bing Cui' 'Qin Hou' 'Tie-Gang Wang' 'Ling Ye' ; Xiao-Yang Yu ; 'Jian-Po Zhang' 'Xiao Zhang' # Attachment '1_cif.cif' data_p-1 _database_code_depnum_ccdc_archive 'CCDC 742278' #TrackingRef '1_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H28 N12 O10 Zn2' _chemical_formula_weight 1015.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5883(17) _cell_length_b 9.790(2) _cell_length_c 11.659(2) _cell_angle_alpha 81.66(3) _cell_angle_beta 83.69(3) _cell_angle_gamma 80.09(3) _cell_volume 951.7(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.772 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 1.345 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.7747 _exptl_absorpt_correction_T_max 0.8772 _exptl_absorpt_process_details ? _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 ? _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 9379 _diffrn_reflns_av_R_equivalents 0.0544 _diffrn_reflns_av_sigmaI/netI 0.0768 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4310 _reflns_number_gt 2723 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0706P)^2^+0.5531P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4310 _refine_ls_number_parameters 315 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1041 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1530 _refine_ls_wR_factor_gt 0.1208 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 0.58312(6) 0.70366(5) 0.76613(5) 0.03297(18) Uani 1 1 d . . . O1 O 0.5099(5) 0.8981(3) 0.8353(3) 0.0429(8) Uani 1 1 d . . . O2 O 0.7796(3) 0.7454(3) 0.6747(3) 0.0340(7) Uani 1 1 d . . . O3 O 1.3669(3) 0.3943(3) 1.0776(3) 0.0336(7) Uani 1 1 d . . . O4 O 1.1991(3) 0.9021(3) 0.9198(3) 0.0373(7) Uani 1 1 d . . . O5 O 1.0104(4) 0.2353(3) 0.7858(3) 0.0414(8) Uani 1 1 d . . . N1 N 0.5248(4) 0.5088(4) 0.7322(3) 0.0349(8) Uani 1 1 d . . . N2 N 0.4117(4) 0.7699(4) 0.6436(3) 0.0382(9) Uani 1 1 d . . . N3 N 0.8906(4) 0.9131(3) 0.7337(3) 0.0344(8) Uani 1 1 d . . . N4 N 1.0028(4) 0.9448(3) 0.7984(3) 0.0353(9) Uani 1 1 d . . . H4 H 1.0064 1.0323 0.7968 0.042 Uiso 1 1 calc R . . N5 N 1.2794(4) 0.2237(3) 1.0026(3) 0.0296(8) Uani 1 1 d . . . N6 N 1.1837(4) 0.1916(3) 0.9245(3) 0.0303(8) Uani 1 1 d . . . H6 H 1.1840 0.1040 0.9229 0.036 Uiso 1 1 calc R . . C1 C 0.3633(6) 0.8995(5) 0.5989(5) 0.0539(14) Uani 1 1 d . . . H1 H 0.4030 0.9709 0.6251 0.065 Uiso 1 1 calc R . . C2 C 0.2550(7) 0.9353(6) 0.5138(5) 0.0637(16) Uani 1 1 d . . . H2 H 0.2266 1.0280 0.4823 0.076 Uiso 1 1 calc R . . C3 C 0.1933(6) 0.8333(7) 0.4789(5) 0.0610(16) Uani 1 1 d . . . H3 H 0.1183 0.8557 0.4247 0.073 Uiso 1 1 calc R . . C4 C 0.2409(5) 0.6922(6) 0.5236(4) 0.0478(13) Uani 1 1 d . . . C5 C 0.3538(5) 0.6670(5) 0.6070(4) 0.0355(10) Uani 1 1 d . . . C6 C 0.1867(7) 0.5769(8) 0.4885(5) 0.0628(16) Uani 1 1 d . . . H6A H 0.1133 0.5929 0.4331 0.075 Uiso 1 1 calc R . . C7 C 0.2393(6) 0.4459(7) 0.5336(5) 0.0616(17) Uani 1 1 d . . . H7 H 0.2000 0.3727 0.5099 0.074 Uiso 1 1 calc R . . C8 C 0.3554(6) 0.4147(5) 0.6183(4) 0.0444(12) Uani 1 1 d . . . C9 C 0.4132(5) 0.5256(5) 0.6545(4) 0.0364(10) Uani 1 1 d . . . C10 C 0.4158(7) 0.2806(6) 0.6710(5) 0.0596(16) Uani 1 1 d . . . H10 H 0.3792 0.2032 0.6524 0.072 Uiso 1 1 calc R . . C11 C 0.5277(7) 0.2621(5) 0.7493(5) 0.0568(15) Uani 1 1 d . . . H11 H 0.5687 0.1729 0.7827 0.068 Uiso 1 1 calc R . . C12 C 0.5793(6) 0.3798(5) 0.7781(4) 0.0465(12) Uani 1 1 d . . . H12 H 0.6550 0.3670 0.8316 0.056 Uiso 1 1 calc R . . C13 C 1.2857(5) 0.3565(4) 1.0044(3) 0.0269(8) Uani 1 1 d . . . C14 C 1.1947(4) 0.4661(4) 0.9274(3) 0.0251(8) Uani 1 1 d . . . C15 C 1.2027(5) 0.6061(4) 0.9289(4) 0.0275(9) Uani 1 1 d . . . H15 H 1.2731 0.6317 0.9741 0.033 Uiso 1 1 calc R . . C16 C 1.1043(5) 0.7084(4) 0.8620(4) 0.0269(8) Uani 1 1 d . . . C17 C 1.1067(5) 0.8568(4) 0.8633(4) 0.0287(9) Uani 1 1 d . . . C18 C 0.8868(5) 0.7807(4) 0.7317(4) 0.0286(9) Uani 1 1 d . . . C19 C 0.9971(5) 0.6705(4) 0.7937(3) 0.0263(8) Uani 1 1 d . . . C20 C 0.9950(5) 0.5300(4) 0.7886(3) 0.0273(8) Uani 1 1 d . . . H20 H 0.9278 0.5040 0.7412 0.033 Uiso 1 1 calc R . . C21 C 1.0938(5) 0.4281(4) 0.8547(4) 0.0273(9) Uani 1 1 d . . . C22 C 1.0905(5) 0.2799(4) 0.8511(4) 0.0291(9) Uani 1 1 d . . . H1WA H 0.426(6) 0.889(5) 0.871(4) 0.031(14) Uiso 1 1 d . . . H1WB H 0.574(11) 0.896(10) 0.888(9) 0.16(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 Zn1 0.0365(3) 0.0278(3) 0.0375(3) -0.0011(2) -0.0161(2) -0.0075(2) O1 0.041(2) 0.0357(17) 0.054(2) -0.0084(16) -0.0141(19) -0.0035(16) O2 0.0406(16) 0.0301(14) 0.0359(17) -0.0037(13) -0.0170(13) -0.0096(13) O3 0.0434(17) 0.0299(14) 0.0322(17) -0.0016(12) -0.0173(13) -0.0120(13) O4 0.0382(16) 0.0242(14) 0.054(2) -0.0061(13) -0.0221(15) -0.0059(13) O5 0.0564(19) 0.0226(14) 0.051(2) -0.0058(14) -0.0278(16) -0.0082(14) N1 0.045(2) 0.0315(18) 0.032(2) -0.0020(15) -0.0100(16) -0.0138(16) N2 0.0363(19) 0.040(2) 0.039(2) 0.0014(17) -0.0144(17) -0.0055(17) N3 0.0397(19) 0.0278(17) 0.039(2) 0.0003(15) -0.0163(16) -0.0098(16) N4 0.044(2) 0.0214(16) 0.044(2) -0.0002(15) -0.0223(17) -0.0088(16) N5 0.0351(18) 0.0225(16) 0.034(2) -0.0027(14) -0.0143(15) -0.0064(14) N6 0.0383(19) 0.0206(15) 0.035(2) -0.0031(14) -0.0138(16) -0.0069(15) C1 0.061(3) 0.041(3) 0.055(3) 0.004(2) -0.018(3) 0.003(3) C2 0.067(4) 0.063(3) 0.055(4) 0.009(3) -0.025(3) 0.006(3) C3 0.046(3) 0.090(4) 0.040(3) 0.005(3) -0.015(2) 0.004(3) C4 0.038(2) 0.083(4) 0.027(3) -0.011(2) 0.001(2) -0.020(3) C5 0.029(2) 0.051(3) 0.029(2) -0.002(2) -0.0074(18) -0.011(2) C6 0.051(3) 0.108(5) 0.040(3) -0.021(3) -0.010(3) -0.029(3) C7 0.055(3) 0.100(5) 0.049(3) -0.037(3) 0.004(3) -0.049(3) C8 0.044(3) 0.056(3) 0.040(3) -0.022(2) 0.007(2) -0.023(2) C9 0.039(2) 0.047(3) 0.030(2) -0.013(2) 0.0008(19) -0.020(2) C10 0.078(4) 0.053(3) 0.058(4) -0.030(3) 0.021(3) -0.036(3) C11 0.078(4) 0.033(2) 0.057(4) -0.003(2) 0.013(3) -0.017(3) C12 0.069(3) 0.033(2) 0.037(3) -0.001(2) -0.006(2) -0.009(2) C13 0.032(2) 0.0243(18) 0.026(2) -0.0023(16) -0.0064(17) -0.0071(17) C14 0.0239(19) 0.0237(18) 0.028(2) -0.0046(16) -0.0015(16) -0.0050(16) C15 0.031(2) 0.0244(18) 0.029(2) -0.0038(16) -0.0092(17) -0.0062(17) C16 0.032(2) 0.0226(18) 0.028(2) -0.0033(16) -0.0058(17) -0.0077(17) C17 0.031(2) 0.0219(18) 0.035(2) -0.0033(17) -0.0081(18) -0.0071(17) C18 0.034(2) 0.0249(19) 0.028(2) -0.0004(16) -0.0098(18) -0.0069(17) C19 0.031(2) 0.0249(18) 0.024(2) -0.0037(16) -0.0050(16) -0.0051(17) C20 0.033(2) 0.0271(19) 0.025(2) -0.0043(16) -0.0110(16) -0.0073(17) C21 0.030(2) 0.0231(18) 0.030(2) -0.0036(16) -0.0046(17) -0.0068(17) C22 0.033(2) 0.0230(18) 0.034(2) -0.0032(17) -0.0097(18) -0.0069(17) _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 1.966(3) . ? Zn1 O3 1.986(3) 2_767 ? Zn1 N2 2.120(4) . ? Zn1 O1 2.143(3) . ? Zn1 N1 2.154(3) . ? O1 H1WA 0.80(5) . ? O1 H1WB 0.87(10) . ? O2 C18 1.312(5) . ? O3 C13 1.290(5) . ? O3 Zn1 1.986(3) 2_767 ? O4 C17 1.257(5) . ? O5 C22 1.248(5) . ? N1 C12 1.325(6) . ? N1 C9 1.364(6) . ? N2 C1 1.315(6) . ? N2 C5 1.336(6) . ? N3 C18 1.306(5) . ? N3 N4 1.387(5) . ? N4 C17 1.344(5) . ? N4 H4 0.8600 . ? N5 C13 1.313(5) . ? N5 N6 1.393(4) . ? N6 C22 1.349(5) . ? N6 H6 0.8600 . ? C1 C2 1.401(7) . ? C1 H1 0.9300 . ? C2 C3 1.338(8) . ? C2 H2 0.9300 . ? C3 C4 1.411(8) . ? C3 H3 0.9300 . ? C4 C5 1.415(6) . ? C4 C6 1.420(8) . ? C5 C9 1.442(6) . ? C6 C7 1.335(9) . ? C6 H6A 0.9300 . ? C7 C8 1.444(8) . ? C7 H7 0.9300 . ? C8 C9 1.403(6) . ? C8 C10 1.404(8) . ? C10 C11 1.370(8) . ? C10 H10 0.9300 . ? C11 C12 1.398(7) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.468(5) . ? C14 C15 1.386(5) . ? C14 C21 1.404(5) . ? C15 C16 1.398(5) . ? C15 H15 0.9300 . ? C16 C19 1.408(5) . ? C16 C17 1.459(5) . ? C18 C19 1.468(5) . ? C19 C20 1.388(5) . ? C20 C21 1.392(5) . ? C20 H20 0.9300 . ? C21 C22 1.463(5) . ? 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 O3 109.66(12) . 2_767 ? O2 Zn1 N2 102.30(14) . . ? O3 Zn1 N2 147.66(14) 2_767 . ? O2 Zn1 O1 98.99(14) . . ? O3 Zn1 O1 91.06(13) 2_767 . ? N2 Zn1 O1 88.68(14) . . ? O2 Zn1 N1 111.25(13) . . ? O3 Zn1 N1 86.42(13) 2_767 . ? N2 Zn1 N1 77.42(14) . . ? O1 Zn1 N1 148.69(16) . . ? Zn1 O1 H1WA 104(3) . . ? Zn1 O1 H1WB 105(6) . . ? H1WA O1 H1WB 105(7) . . ? C18 O2 Zn1 116.5(3) . . ? C13 O3 Zn1 127.8(3) . 2_767 ? C12 N1 C9 117.9(4) . . ? C12 N1 Zn1 128.9(3) . . ? C9 N1 Zn1 113.2(3) . . ? C1 N2 C5 118.6(4) . . ? C1 N2 Zn1 126.3(3) . . ? C5 N2 Zn1 115.1(3) . . ? C18 N3 N4 116.7(3) . . ? C17 N4 N3 128.6(3) . . ? C17 N4 H4 115.7 . . ? N3 N4 H4 115.7 . . ? C13 N5 N6 117.3(3) . . ? C22 N6 N5 128.5(3) . . ? C22 N6 H6 115.7 . . ? N5 N6 H6 115.7 . . ? N2 C1 C2 123.3(5) . . ? N2 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C3 C2 C1 118.5(5) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 120.7(5) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C5 116.2(5) . . ? C3 C4 C6 124.7(5) . . ? C5 C4 C6 119.1(5) . . ? N2 C5 C4 122.6(4) . . ? N2 C5 C9 117.4(4) . . ? C4 C5 C9 120.0(4) . . ? C7 C6 C4 121.1(5) . . ? C7 C6 H6A 119.4 . . ? C4 C6 H6A 119.4 . . ? C6 C7 C8 121.8(5) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C9 C8 C10 115.5(5) . . ? C9 C8 C7 118.9(5) . . ? C10 C8 C7 125.6(5) . . ? N1 C9 C8 124.1(4) . . ? N1 C9 C5 116.9(4) . . ? C8 C9 C5 119.1(4) . . ? C11 C10 C8 121.0(5) . . ? C11 C10 H10 119.5 . . ? C8 C10 H10 119.5 . . ? C10 C11 C12 118.9(5) . . ? C10 C11 H11 120.6 . . ? C12 C11 H11 120.6 . . ? N1 C12 C11 122.6(5) . . ? N1 C12 H12 118.7 . . ? C11 C12 H12 118.7 . . ? O3 C13 N5 120.7(4) . . ? O3 C13 C14 118.1(3) . . ? N5 C13 C14 121.1(4) . . ? C15 C14 C21 119.9(4) . . ? C15 C14 C13 120.9(4) . . ? C21 C14 C13 119.1(3) . . ? C14 C15 C16 119.4(4) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C15 C16 C19 120.6(3) . . ? C15 C16 C17 121.0(4) . . ? C19 C16 C17 118.3(3) . . ? O4 C17 N4 121.0(3) . . ? O4 C17 C16 123.6(3) . . ? N4 C17 C16 115.4(4) . . ? N3 C18 O2 119.0(3) . . ? N3 C18 C19 121.8(4) . . ? O2 C18 C19 119.2(3) . . ? C20 C19 C16 119.5(3) . . ? C20 C19 C18 121.4(4) . . ? C16 C19 C18 119.1(3) . . ? C19 C20 C21 119.8(4) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C20 C21 C14 120.6(3) . . ? C20 C21 C22 120.1(4) . . ? C14 C21 C22 119.3(3) . . ? O5 C22 N6 121.2(3) . . ? O5 C22 C21 124.3(4) . . ? N6 C22 C21 114.5(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1WB N5 0.87(10) 2.00(10) 2.761(5) 146(8) 2_767 N4 H4 O5 0.86 1.98 2.838(4) 177.3 1_565 N6 H6 O4 0.86 1.96 2.823(4) 176.5 1_545 O1 H1WA O4 0.80(5) 1.96(5) 2.738(5) 164(5) 1_455 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.506 _refine_diff_density_min -1.078 _refine_diff_density_rms 0.109 # Attachment '2_cif.CIF' data_p-2 _database_code_depnum_ccdc_archive 'CCDC 742279' #TrackingRef '2_cif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H24 N12 O8 Zn2' _chemical_formula_weight 931.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9067(14) _cell_length_b 9.7485(19) _cell_length_c 12.966(3) _cell_angle_alpha 80.71(3) _cell_angle_beta 76.27(3) _cell_angle_gamma 80.67(3) _cell_volume 830.0(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.864 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 1.529 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.8031 _exptl_absorpt_correction_T_max 0.9849 _exptl_absorpt_process_details ? _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 ? _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 8219 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.0601 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3755 _reflns_number_gt 2745 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0426P)^2^+0.6588P] 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 3755 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1036 _refine_ls_wR_factor_gt 0.0935 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.18635(6) 0.77344(4) 0.16726(3) 0.02842(14) Uani 1 1 d . . . O1 O -0.4006(3) 0.2957(2) 0.75569(17) 0.0251(5) Uani 1 1 d . . . O2 O 0.0349(4) 0.5568(2) 0.19626(19) 0.0373(6) Uani 1 1 d . . . O3 O -0.1762(4) 0.0809(2) 0.38219(19) 0.0336(6) Uani 1 1 d . . . O4 O -0.3054(4) 0.7804(2) 0.55657(19) 0.0330(6) Uani 1 1 d . . . N1 N 0.1896(4) 0.9829(3) 0.1004(2) 0.0256(6) Uani 1 1 d . . . N2 N 0.2758(4) 0.7482(3) 0.0095(2) 0.0251(6) Uani 1 1 d . . . N3 N -0.0598(4) 0.7387(3) 0.2872(2) 0.0244(6) Uani 1 1 d . . . N4 N -0.3572(4) 0.1148(3) 0.6600(2) 0.0279(6) Uani 1 1 d . . . N5 N -0.1484(4) 0.7934(3) 0.3822(2) 0.0244(6) Uani 1 1 d . . . H5 H -0.1494 0.8819 0.3816 0.029 Uiso 1 1 calc R . . N6 N -0.2998(5) 0.0669(3) 0.5609(2) 0.0293(7) Uani 1 1 d . . . H6 H -0.3089 -0.0200 0.5606 0.035 Uiso 1 1 calc R . . C1 C 0.1393(5) 1.0973(4) 0.1508(3) 0.0316(8) Uani 1 1 d . . . H1 H 0.0956 1.0863 0.2249 0.038 Uiso 1 1 calc R . . C2 C 0.1501(6) 1.2315(4) 0.0966(3) 0.0348(8) Uani 1 1 d . . . H2 H 0.1139 1.3093 0.1335 0.042 Uiso 1 1 calc R . . C3 C 0.2151(5) 1.2469(4) -0.0120(3) 0.0340(8) Uani 1 1 d . . . H3 H 0.2216 1.3360 -0.0502 0.041 Uiso 1 1 calc R . . C4 C 0.2711(5) 1.1299(3) -0.0653(3) 0.0282(7) Uani 1 1 d . . . H4 H 0.3187 1.1392 -0.1391 0.034 Uiso 1 1 calc R . . C5 C 0.2553(5) 0.9989(3) -0.0071(3) 0.0230(7) Uani 1 1 d . . . C6 C 0.3079(5) 0.8673(3) -0.0575(2) 0.0223(7) Uani 1 1 d . . . C7 C 0.3827(5) 0.8646(4) -0.1662(3) 0.0297(8) Uani 1 1 d . . . H7 H 0.4038 0.9473 -0.2117 0.036 Uiso 1 1 calc R . . C8 C 0.4256(6) 0.7376(4) -0.2060(3) 0.0354(8) Uani 1 1 d . . . H8 H 0.4775 0.7337 -0.2787 0.042 Uiso 1 1 calc R . . C9 C 0.3906(6) 0.6162(4) -0.1369(3) 0.0358(9) Uani 1 1 d . . . H9 H 0.4178 0.5296 -0.1623 0.043 Uiso 1 1 calc R . . C10 C 0.3147(5) 0.6261(3) -0.0299(3) 0.0313(8) Uani 1 1 d . . . H10 H 0.2895 0.5447 0.0167 0.038 Uiso 1 1 calc R . . C11 C -0.2314(5) 0.2885(3) 0.4672(2) 0.0192(6) Uani 1 1 d . . . C12 C -0.2320(5) 0.1389(3) 0.4653(3) 0.0252(7) Uani 1 1 d . . . C13 C -0.3001(4) 0.4859(3) 0.5670(2) 0.0183(6) Uani 1 1 d . . . H13 H -0.3465 0.5237 0.6312 0.022 Uiso 1 1 calc R . . C14 C -0.2999(5) 0.3442(3) 0.5648(2) 0.0185(6) Uani 1 1 d . . . C15 C -0.3573(5) 0.2480(3) 0.6625(2) 0.0207(7) Uani 1 1 d . . . C16 C -0.2325(5) 0.7223(3) 0.4747(3) 0.0214(7) Uani 1 1 d . . . C17 C -0.2306(4) 0.5717(3) 0.4727(2) 0.0188(6) Uani 1 1 d . . . C18 C -0.1558(5) 0.5147(3) 0.3764(2) 0.0197(6) Uani 1 1 d . . . C19 C -0.0602(5) 0.6045(3) 0.2813(2) 0.0232(7) Uani 1 1 d . . . C20 C -0.1575(5) 0.3738(3) 0.3740(2) 0.0224(7) Uani 1 1 d . . . H20 H -0.1092 0.3360 0.3099 0.027 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 0.0365(2) 0.0316(2) 0.0144(2) 0.00484(15) -0.00092(15) -0.01087(17) O1 0.0353(13) 0.0234(11) 0.0138(11) -0.0009(9) -0.0005(9) -0.0045(10) O2 0.0562(17) 0.0307(13) 0.0171(12) -0.0011(10) 0.0088(11) -0.0097(12) O3 0.0596(17) 0.0169(11) 0.0214(13) -0.0043(9) 0.0002(11) -0.0079(11) O4 0.0523(16) 0.0173(11) 0.0235(13) -0.0044(9) 0.0072(11) -0.0088(11) N1 0.0290(15) 0.0265(14) 0.0194(14) -0.0002(11) -0.0015(11) -0.0063(12) N2 0.0293(15) 0.0251(13) 0.0181(14) 0.0017(11) -0.0001(11) -0.0077(12) N3 0.0325(16) 0.0212(13) 0.0160(14) 0.0024(11) 0.0012(11) -0.0075(12) N4 0.0440(18) 0.0212(13) 0.0164(14) 0.0032(11) -0.0023(12) -0.0105(13) N5 0.0361(16) 0.0135(12) 0.0209(14) 0.0004(10) 0.0003(12) -0.0071(11) N6 0.0503(19) 0.0132(12) 0.0222(15) 0.0003(11) -0.0018(13) -0.0092(13) C1 0.036(2) 0.0344(18) 0.0213(18) -0.0050(14) 0.0003(15) -0.0053(16) C2 0.038(2) 0.0312(18) 0.033(2) -0.0040(15) -0.0075(16) -0.0007(16) C3 0.039(2) 0.0243(17) 0.038(2) 0.0055(15) -0.0099(17) -0.0086(16) C4 0.0337(19) 0.0281(17) 0.0208(17) 0.0041(13) -0.0027(14) -0.0103(15) C5 0.0226(16) 0.0255(16) 0.0191(16) 0.0016(13) -0.0019(13) -0.0064(13) C6 0.0239(16) 0.0256(16) 0.0164(15) 0.0021(12) -0.0028(13) -0.0068(13) C7 0.038(2) 0.0303(17) 0.0180(17) 0.0033(13) -0.0025(14) -0.0080(16) C8 0.042(2) 0.043(2) 0.0180(18) -0.0052(15) 0.0006(15) -0.0061(18) C9 0.049(2) 0.0322(19) 0.0262(19) -0.0054(15) -0.0044(17) -0.0079(17) C10 0.040(2) 0.0244(17) 0.0274(19) -0.0005(14) -0.0039(15) -0.0056(15) C11 0.0280(17) 0.0130(13) 0.0155(15) 0.0022(11) -0.0040(13) -0.0049(12) C12 0.0356(19) 0.0166(14) 0.0212(17) 0.0000(12) -0.0033(14) -0.0033(14) C13 0.0229(16) 0.0167(14) 0.0135(15) -0.0036(11) 0.0001(12) -0.0018(12) C14 0.0233(16) 0.0159(14) 0.0134(14) 0.0031(11) -0.0012(12) -0.0032(12) C15 0.0249(17) 0.0194(15) 0.0163(15) 0.0006(12) -0.0023(13) -0.0049(13) C16 0.0268(17) 0.0141(14) 0.0204(16) 0.0018(12) -0.0016(13) -0.0037(13) C17 0.0212(16) 0.0152(14) 0.0197(16) -0.0019(11) -0.0027(12) -0.0042(12) C18 0.0251(16) 0.0169(14) 0.0145(15) 0.0018(12) -0.0002(12) -0.0050(13) C19 0.0287(18) 0.0202(15) 0.0185(16) 0.0010(12) -0.0011(13) -0.0066(14) C20 0.0324(18) 0.0177(14) 0.0153(15) -0.0026(12) -0.0007(13) -0.0039(14) _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 O1 1.950(2) 2_566 ? Zn1 N2 2.035(3) . ? Zn1 N3 2.045(3) . ? Zn1 N1 2.087(3) . ? Zn1 O2 2.444(2) . ? O1 C15 1.316(4) . ? O1 Zn1 1.950(2) 2_566 ? O2 C19 1.259(4) . ? O3 C12 1.248(4) . ? O4 C16 1.245(4) . ? N1 C1 1.340(4) . ? N1 C5 1.351(4) . ? N2 C10 1.333(4) . ? N2 C6 1.348(4) . ? N3 C19 1.323(4) . ? N3 N5 1.388(4) . ? N4 C15 1.304(4) . ? N4 N6 1.384(4) . ? N5 C16 1.337(4) . ? N5 H5 0.8600 . ? N6 C12 1.341(4) . ? N6 H6 0.8600 . ? C1 C2 1.386(5) . ? C1 H1 0.9300 . ? C2 C3 1.365(5) . ? C2 H2 0.9300 . ? C3 C4 1.384(5) . ? C3 H3 0.9300 . ? C4 C5 1.381(4) . ? C4 H4 0.9300 . ? C5 C6 1.487(4) . ? C6 C7 1.384(4) . ? C7 C8 1.379(5) . ? C7 H7 0.9300 . ? C8 C9 1.382(5) . ? C8 H8 0.9300 . ? C9 C10 1.375(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C20 1.391(4) . ? C11 C14 1.406(4) . ? C11 C12 1.463(4) . ? C13 C14 1.386(4) . ? C13 C17 1.395(4) . ? C13 H13 0.9300 . ? C14 C15 1.462(4) . ? C16 C17 1.470(4) . ? C17 C18 1.401(4) . ? C18 C20 1.380(4) . ? C18 C19 1.475(4) . ? C20 H20 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 N2 111.90(11) 2_566 . ? O1 Zn1 N3 100.27(10) 2_566 . ? N2 Zn1 N3 136.32(11) . . ? O1 Zn1 N1 113.10(10) 2_566 . ? N2 Zn1 N1 80.33(11) . . ? N3 Zn1 N1 113.82(11) . . ? O1 Zn1 O2 97.72(9) 2_566 . ? N2 Zn1 O2 87.94(9) . . ? N3 Zn1 O2 58.26(9) . . ? N1 Zn1 O2 149.17(10) . . ? C15 O1 Zn1 110.4(2) . 2_566 ? C19 O2 Zn1 82.24(18) . . ? C1 N1 C5 118.7(3) . . ? C1 N1 Zn1 128.1(2) . . ? C5 N1 Zn1 113.1(2) . . ? C10 N2 C6 119.4(3) . . ? C10 N2 Zn1 125.6(2) . . ? C6 N2 Zn1 114.9(2) . . ? C19 N3 N5 120.0(2) . . ? C19 N3 Zn1 98.4(2) . . ? N5 N3 Zn1 135.0(2) . . ? C15 N4 N6 117.5(3) . . ? C16 N5 N3 126.5(3) . . ? C16 N5 H5 116.8 . . ? N3 N5 H5 116.8 . . ? C12 N6 N4 128.2(3) . . ? C12 N6 H6 115.9 . . ? N4 N6 H6 115.9 . . ? N1 C1 C2 122.4(3) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C3 C2 C1 118.5(3) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 119.9(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 118.9(3) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? N1 C5 C4 121.5(3) . . ? N1 C5 C6 115.7(3) . . ? C4 C5 C6 122.8(3) . . ? N2 C6 C7 121.1(3) . . ? N2 C6 C5 115.7(3) . . ? C7 C6 C5 123.2(3) . . ? C8 C7 C6 119.2(3) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C7 C8 C9 119.4(3) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C10 C9 C8 118.6(3) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? N2 C10 C9 122.4(3) . . ? N2 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? C20 C11 C14 120.3(3) . . ? C20 C11 C12 120.3(3) . . ? C14 C11 C12 119.3(3) . . ? O3 C12 N6 121.6(3) . . ? O3 C12 C11 123.7(3) . . ? N6 C12 C11 114.7(3) . . ? C14 C13 C17 119.9(3) . . ? C14 C13 H13 120.1 . . ? C17 C13 H13 120.1 . . ? C13 C14 C11 119.6(3) . . ? C13 C14 C15 122.0(3) . . ? C11 C14 C15 118.3(3) . . ? N4 C15 O1 119.0(3) . . ? N4 C15 C14 121.7(3) . . ? O1 C15 C14 119.1(3) . . ? O4 C16 N5 121.8(3) . . ? O4 C16 C17 122.8(3) . . ? N5 C16 C17 115.4(3) . . ? C13 C17 C18 120.3(3) . . ? C13 C17 C16 119.9(3) . . ? C18 C17 C16 119.7(3) . . ? C20 C18 C17 119.8(3) . . ? C20 C18 C19 121.2(3) . . ? C17 C18 C19 118.8(3) . . ? O2 C19 N3 117.9(3) . . ? O2 C19 C18 122.6(3) . . ? N3 C19 C18 119.3(3) . . ? C18 C20 C11 120.1(3) . . ? C18 C20 H20 119.9 . . ? C11 C20 H20 119.9 . . ? 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 H5 O3 0.86 1.92 2.778(3) 175.1 1_565 N6 H6 O4 0.86 1.95 2.809(3) 175.3 1_545 C8 H8 O4 0.93 2.33 3.198(4) 156.2 1_654 C1 H1 O3 0.93 2.42 3.260(4) 149.9 1_565 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.499 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.102 # Attachment '3_cif.CIF' data_p-3 _database_code_depnum_ccdc_archive 'CCDC 742280' #TrackingRef '3_cif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H6 N4 O5 Zn' _chemical_formula_weight 327.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3032(15) _cell_length_b 8.0590(16) _cell_length_c 9.7201(19) _cell_angle_alpha 111.09(3) _cell_angle_beta 105.97(3) _cell_angle_gamma 95.67(3) _cell_volume 500.51(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.173 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 2.485 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7530 _exptl_absorpt_correction_T_max 0.7839 _exptl_absorpt_process_details ? _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 ? _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 4977 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2283 _reflns_number_gt 1946 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0300P)^2^+0.9672P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2283 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0854 _refine_ls_wR_factor_gt 0.0697 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _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 0.44895(5) 0.64923(5) 0.89033(4) 0.01923(13) Uani 1 1 d . . . O1 O 0.5016(4) 0.8120(3) 0.7948(3) 0.0243(5) Uani 1 1 d . . . O2 O 0.1572(4) 0.5829(4) 0.1748(3) 0.0355(7) Uani 1 1 d . . . O3 O 0.6010(3) 0.6121(3) 1.2117(2) 0.0203(5) Uani 1 1 d . . . O4 O 1.0456(4) 1.1761(3) 1.2047(3) 0.0271(6) Uani 1 1 d . . . C1 C 0.8656(4) 0.8699(4) 1.3592(3) 0.0141(6) Uani 1 1 d . . . C2 C 0.7166(4) 0.7416(4) 1.2118(3) 0.0161(6) Uani 1 1 d . . . C3 C 0.8924(4) 0.8429(4) 1.4965(3) 0.0169(6) Uani 1 1 d . . . H3 H 0.8216 0.7393 1.4948 0.020 Uiso 1 1 calc R . . C4 C 0.9741(4) 1.0279(4) 1.3638(3) 0.0143(6) Uani 1 1 d . . . C5 C 0.9492(5) 1.0474(4) 1.2153(4) 0.0191(6) Uani 1 1 d . . . C6 C 0.5914(4) 1.0542(4) 0.6609(4) 0.0184(6) Uani 1 1 d . . . H6 H 0.6529 1.0901 0.7677 0.022 Uiso 1 1 calc R . . C7 C 0.4233(5) 0.7583(4) 0.6430(4) 0.0198(6) Uani 1 1 d . . . C8 C 0.2466(5) 0.6464(4) 0.3182(4) 0.0210(7) Uani 1 1 d . . . C9 C 0.4658(4) 0.8843(4) 0.5725(3) 0.0163(6) Uani 1 1 d . . . C10 C 0.3746(4) 0.8291(4) 0.4096(3) 0.0156(6) Uani 1 1 d . . . N1 N 0.2281(5) 0.5502(4) 0.4011(3) 0.0296(7) Uani 1 1 d . . . H1 H 0.1562 0.4419 0.3482 0.036 Uiso 1 1 calc R . . N2 N 0.3080(5) 0.5991(4) 0.5611(3) 0.0301(7) Uani 1 1 d . . . N3 N 0.6929(4) 0.7684(4) 1.0830(3) 0.0189(6) Uani 1 1 d . . . N4 N 0.8158(4) 0.9160(4) 1.0889(3) 0.0241(6) Uani 1 1 d . . . H4 H 0.8046 0.9233 1.0010 0.029 Uiso 1 1 calc R . . O1W O 0.2248(4) 0.6881(4) 0.9653(3) 0.0303(6) Uani 1 1 d . . . H1WA H 0.208(9) 0.629(9) 1.011(8) 0.08(2) Uiso 1 1 d . . . H1WB H 0.125(10) 0.710(9) 0.915(8) 0.09(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 0.0242(2) 0.01561(19) 0.01293(18) 0.00723(14) 0.00016(14) -0.00517(13) O1 0.0348(13) 0.0199(12) 0.0144(10) 0.0093(9) 0.0033(10) -0.0047(10) O2 0.0427(15) 0.0332(15) 0.0157(11) 0.0105(11) -0.0041(11) -0.0183(12) O3 0.0278(12) 0.0116(10) 0.0155(10) 0.0013(8) 0.0066(9) -0.0039(9) O4 0.0364(14) 0.0220(12) 0.0171(11) 0.0104(10) 0.0028(10) -0.0099(10) C1 0.0162(14) 0.0113(13) 0.0108(13) 0.0028(11) 0.0017(11) 0.0003(11) C2 0.0166(14) 0.0141(14) 0.0138(14) 0.0055(11) 0.0011(12) -0.0005(11) C3 0.0162(14) 0.0165(14) 0.0164(14) 0.0091(12) 0.0020(12) -0.0026(11) C4 0.0177(14) 0.0131(14) 0.0118(13) 0.0060(11) 0.0042(11) 0.0013(11) C5 0.0206(15) 0.0210(16) 0.0141(14) 0.0100(12) 0.0016(12) -0.0018(12) C6 0.0216(15) 0.0194(15) 0.0125(13) 0.0086(12) 0.0016(12) 0.0003(12) C7 0.0245(16) 0.0207(16) 0.0152(14) 0.0110(12) 0.0047(12) 0.0001(12) C8 0.0244(16) 0.0164(15) 0.0168(14) 0.0055(12) 0.0033(13) -0.0031(12) C9 0.0188(15) 0.0164(15) 0.0143(14) 0.0087(12) 0.0040(12) 0.0020(11) C10 0.0187(15) 0.0126(14) 0.0137(14) 0.0041(11) 0.0049(12) 0.0017(11) N1 0.0426(18) 0.0158(14) 0.0163(13) 0.0054(11) -0.0031(13) -0.0130(12) N2 0.0391(17) 0.0266(16) 0.0183(14) 0.0148(12) -0.0017(13) -0.0105(13) N3 0.0233(13) 0.0161(13) 0.0114(12) 0.0051(10) 0.0008(10) -0.0056(10) N4 0.0310(15) 0.0255(15) 0.0097(11) 0.0097(11) -0.0005(11) -0.0093(12) O1W 0.0254(14) 0.0436(17) 0.0260(13) 0.0212(13) 0.0060(11) 0.0046(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 1.923(2) 2_667 ? Zn1 O1 1.925(2) . ? Zn1 O1W 1.976(3) . ? Zn1 N3 2.033(3) . ? O1 C7 1.311(4) . ? O2 C8 1.245(4) . ? O3 C2 1.276(4) . ? O3 Zn1 1.923(2) 2_667 ? O4 C5 1.246(4) . ? C1 C3 1.393(4) . ? C1 C4 1.411(4) . ? C1 C2 1.469(4) . ? C2 N3 1.314(4) . ? C3 C4 1.389(4) 2_778 ? C3 H3 0.9300 . ? C4 C3 1.389(4) 2_778 ? C4 C5 1.472(4) . ? C5 N4 1.335(4) . ? C6 C9 1.388(4) . ? C6 C10 1.388(4) 2_676 ? C6 H6 0.9300 . ? C7 N2 1.293(4) . ? C7 C9 1.467(4) . ? C8 N1 1.326(4) . ? C8 C10 1.469(4) . ? C9 C10 1.415(4) . ? C10 C6 1.388(4) 2_676 ? N1 N2 1.388(4) . ? N1 H1 0.8600 . ? N3 N4 1.391(4) . ? N4 H4 0.8600 . ? O1W H1WA 0.79(7) . ? O1W H1WB 0.83(7) . ? 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 124.17(10) 2_667 . ? O3 Zn1 O1W 102.53(12) 2_667 . ? O1 Zn1 O1W 112.08(12) . . ? O3 Zn1 N3 115.59(11) 2_667 . ? O1 Zn1 N3 95.39(10) . . ? O1W Zn1 N3 106.28(12) . . ? C7 O1 Zn1 119.3(2) . . ? C2 O3 Zn1 133.6(2) . 2_667 ? C3 C1 C4 119.6(3) . . ? C3 C1 C2 120.6(3) . . ? C4 C1 C2 119.7(3) . . ? O3 C2 N3 120.0(3) . . ? O3 C2 C1 119.7(3) . . ? N3 C2 C1 120.1(3) . . ? C4 C3 C1 119.5(3) 2_778 . ? C4 C3 H3 120.3 2_778 . ? C1 C3 H3 120.3 . . ? C3 C4 C1 120.9(3) 2_778 . ? C3 C4 C5 120.9(3) 2_778 . ? C1 C4 C5 118.1(3) . . ? O4 C5 N4 120.9(3) . . ? O4 C5 C4 123.4(3) . . ? N4 C5 C4 115.6(3) . . ? C9 C6 C10 120.2(3) . 2_676 ? C9 C6 H6 119.9 . . ? C10 C6 H6 119.9 2_676 . ? N2 C7 O1 119.4(3) . . ? N2 C7 C9 122.2(3) . . ? O1 C7 C9 118.4(3) . . ? O2 C8 N1 120.7(3) . . ? O2 C8 C10 124.6(3) . . ? N1 C8 C10 114.7(3) . . ? C6 C9 C10 119.7(3) . . ? C6 C9 C7 121.9(3) . . ? C10 C9 C7 118.3(3) . . ? C6 C10 C9 120.0(3) 2_676 . ? C6 C10 C8 121.4(3) 2_676 . ? C9 C10 C8 118.6(3) . . ? C8 N1 N2 129.3(3) . . ? C8 N1 H1 115.3 . . ? N2 N1 H1 115.3 . . ? C7 N2 N1 116.8(3) . . ? C2 N3 N4 118.5(2) . . ? C2 N3 Zn1 123.6(2) . . ? N4 N3 Zn1 116.08(19) . . ? C5 N4 N3 127.5(3) . . ? C5 N4 H4 116.2 . . ? N3 N4 H4 116.2 . . ? Zn1 O1W H1WA 113(5) . . ? Zn1 O1W H1WB 123(4) . . ? H1WA O1W H1WB 115(6) . . ? 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 O1W H1WA O2 0.79(7) 1.87(7) 2.611(4) 156(7) 1_556 O1W H1WB O4 0.83(7) 1.99(7) 2.786(4) 161(6) 2_677 N1 H1 O4 0.86 2.02 2.859(4) 165.4 1_444 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.457 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.112 # Attachment '4_cif.CIF' data_p1 _database_code_depnum_ccdc_archive 'CCDC 742281' #TrackingRef '4_cif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H12 Cd N6 O4' _chemical_formula_weight 536.79 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' Cd Cd -0.8075 1.2024 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7690(13) _cell_length_b 10.4090(14) _cell_length_c 10.9897(14) _cell_angle_alpha 85.332(2) _cell_angle_beta 66.104(2) _cell_angle_gamma 71.615(3) _cell_volume 968.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.841 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 1.175 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8481 _exptl_absorpt_correction_T_max 0.8866 _exptl_absorpt_process_details ? _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 ? _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 7104 _diffrn_reflns_av_R_equivalents 0.0577 _diffrn_reflns_av_sigmaI/netI 0.0857 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4763 _reflns_number_gt 3595 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0188P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4763 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0706 _refine_ls_wR_factor_gt 0.0641 _refine_ls_goodness_of_fit_ref 0.925 _refine_ls_restrained_S_all 0.925 _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 Cd1 Cd 0.35836(3) 0.57219(2) 0.16704(3) 0.02542(8) Uani 1 1 d . . . C1 C 0.4055(4) 0.8054(3) 0.2157(3) 0.0248(7) Uani 1 1 d . . . C2 C 0.2150(4) 1.0499(3) 0.1560(3) 0.0241(7) Uani 1 1 d . . . C3 C 0.4554(4) 0.9266(3) 0.1962(3) 0.0212(7) Uani 1 1 d . . . C4 C 0.3636(4) 1.0474(3) 0.1619(3) 0.0204(7) Uani 1 1 d . . . C5 C 0.5969(4) 0.9230(3) 0.1993(3) 0.0231(7) Uani 1 1 d . . . H5 H 0.6584 0.8441 0.2210 0.028 Uiso 1 1 calc R . . C6 C 0.4159(4) 1.1599(3) 0.1295(3) 0.0207(7) Uani 1 1 d . . . H6 H 0.3561 1.2380 0.1052 0.025 Uiso 1 1 calc R . . C7 C 0.6473(4) 1.0370(3) 0.1700(3) 0.0199(7) Uani 1 1 d . . . C8 C 0.5580(4) 1.1560(3) 0.1332(3) 0.0193(7) Uani 1 1 d . . . C9 C 0.7985(4) 1.0331(3) 0.1714(3) 0.0264(7) Uani 1 1 d . . . C10 C 0.6224(4) 1.2697(3) 0.0932(3) 0.0215(7) Uani 1 1 d . . . C11 C 0.4140(5) 0.3905(4) 0.4098(4) 0.0434(10) Uani 1 1 d . . . H11 H 0.4958 0.4269 0.3900 0.052 Uiso 1 1 calc R . . C12 C 0.3993(6) 0.2896(5) 0.5019(4) 0.0595(13) Uani 1 1 d . . . H12 H 0.4704 0.2589 0.5421 0.071 Uiso 1 1 calc R . . C13 C 0.2791(6) 0.2371(4) 0.5316(4) 0.0596(13) Uani 1 1 d . . . H13 H 0.2684 0.1691 0.5920 0.072 Uiso 1 1 calc R . . C14 C 0.1713(5) 0.2846(4) 0.4719(4) 0.0417(10) Uani 1 1 d . . . C15 C 0.1966(4) 0.3855(3) 0.3779(3) 0.0303(8) Uani 1 1 d . . . C16 C 0.0921(4) 0.4349(3) 0.3106(3) 0.0299(8) Uani 1 1 d . . . C17 C 0.0257(5) 0.5740(4) 0.1540(4) 0.0434(10) Uani 1 1 d . . . H17 H 0.0471 0.6366 0.0892 0.052 Uiso 1 1 calc R . . C18 C -0.1064(5) 0.5340(4) 0.1817(4) 0.0492(11) Uani 1 1 d . . . H18 H -0.1734 0.5711 0.1385 0.059 Uiso 1 1 calc R . . C19 C -0.1354(5) 0.4385(4) 0.2742(4) 0.0520(11) Uani 1 1 d . . . H19 H -0.2208 0.4077 0.2917 0.062 Uiso 1 1 calc R . . C20 C -0.0371(5) 0.3871(4) 0.3425(4) 0.0407(9) Uani 1 1 d . . . C21 C -0.0590(6) 0.2861(4) 0.4401(4) 0.0553(12) Uani 1 1 d . . . H21 H -0.1444 0.2541 0.4618 0.066 Uiso 1 1 calc R . . C22 C 0.0394(6) 0.2372(4) 0.5005(4) 0.0543(12) Uani 1 1 d . . . H22 H 0.0221 0.1712 0.5622 0.065 Uiso 1 1 calc R . . N1 N 0.2721(3) 0.8105(3) 0.2094(3) 0.0263(6) Uani 1 1 d . . . N2 N 0.1798(3) 0.9330(2) 0.1835(3) 0.0268(6) Uani 1 1 d . . . H2 H 0.0906 0.9339 0.1852 0.032 Uiso 1 1 calc R . . N3 N 0.8380(3) 1.1474(3) 0.1342(3) 0.0318(7) Uani 1 1 d . . . H3 H 0.9255 1.1469 0.1356 0.038 Uiso 1 1 calc R . . N4 N 0.7564(3) 1.2661(3) 0.0936(3) 0.0298(7) Uani 1 1 d . . . N5 N 0.3166(3) 0.4364(3) 0.3497(3) 0.0308(7) Uani 1 1 d . . . N6 N 0.1230(3) 0.5277(3) 0.2150(3) 0.0315(7) Uani 1 1 d . . . O1 O 0.4922(3) 0.6890(2) 0.2322(2) 0.0335(6) Uani 1 1 d . . . O2 O 0.5443(3) 1.3786(2) 0.0507(2) 0.0257(5) Uani 1 1 d . . . O3 O 0.1276(3) 1.1519(2) 0.1263(2) 0.0335(6) Uani 1 1 d . . . O4 O 0.8840(3) 0.9332(2) 0.2048(3) 0.0399(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.02622(14) 0.01957(12) 0.03168(14) 0.00562(9) -0.01080(11) -0.01081(10) C1 0.0276(19) 0.0221(16) 0.0264(18) 0.0038(13) -0.0109(15) -0.0104(15) C2 0.0203(17) 0.0261(17) 0.0270(18) 0.0011(13) -0.0098(14) -0.0083(15) C3 0.0223(17) 0.0199(15) 0.0218(16) 0.0038(12) -0.0084(14) -0.0084(14) C4 0.0178(16) 0.0204(16) 0.0201(16) 0.0006(13) -0.0071(13) -0.0027(14) C5 0.0253(18) 0.0162(15) 0.0356(19) 0.0083(13) -0.0196(15) -0.0084(14) C6 0.0181(16) 0.0167(15) 0.0258(17) 0.0011(12) -0.0097(14) -0.0023(13) C7 0.0194(17) 0.0185(15) 0.0258(17) 0.0057(12) -0.0130(14) -0.0070(14) C8 0.0192(16) 0.0176(15) 0.0203(16) 0.0037(12) -0.0087(13) -0.0045(13) C9 0.0246(18) 0.0251(17) 0.035(2) 0.0083(14) -0.0153(16) -0.0127(15) C10 0.0231(18) 0.0171(15) 0.0245(17) 0.0045(12) -0.0102(14) -0.0065(14) C11 0.043(2) 0.052(2) 0.039(2) 0.0054(19) -0.017(2) -0.019(2) C12 0.067(3) 0.066(3) 0.051(3) 0.019(2) -0.034(3) -0.018(3) C13 0.086(4) 0.052(3) 0.039(3) 0.019(2) -0.027(3) -0.019(3) C14 0.056(3) 0.034(2) 0.027(2) 0.0027(16) -0.0042(19) -0.020(2) C15 0.033(2) 0.0250(17) 0.0251(18) -0.0003(14) -0.0004(16) -0.0136(16) C16 0.031(2) 0.0257(18) 0.0268(19) -0.0038(14) -0.0019(16) -0.0128(16) C17 0.038(2) 0.044(2) 0.048(2) 0.0028(18) -0.020(2) -0.010(2) C18 0.028(2) 0.062(3) 0.058(3) -0.012(2) -0.017(2) -0.012(2) C19 0.032(2) 0.058(3) 0.066(3) -0.016(2) -0.009(2) -0.024(2) C20 0.036(2) 0.043(2) 0.038(2) -0.0069(17) -0.0006(18) -0.023(2) C21 0.054(3) 0.052(3) 0.055(3) -0.001(2) 0.002(2) -0.041(2) C22 0.064(3) 0.049(3) 0.044(3) 0.009(2) -0.005(2) -0.034(3) N1 0.0254(16) 0.0201(13) 0.0392(17) 0.0044(12) -0.0176(14) -0.0093(12) N2 0.0168(14) 0.0213(14) 0.0455(18) 0.0034(12) -0.0167(13) -0.0050(12) N3 0.0237(16) 0.0249(15) 0.060(2) 0.0175(13) -0.0280(15) -0.0131(13) N4 0.0276(16) 0.0204(14) 0.0494(18) 0.0141(12) -0.0233(15) -0.0106(13) N5 0.0309(17) 0.0335(16) 0.0244(15) 0.0029(12) -0.0067(13) -0.0117(14) N6 0.0266(16) 0.0282(15) 0.0365(17) 0.0002(13) -0.0089(14) -0.0088(14) O1 0.0352(15) 0.0206(12) 0.0571(16) 0.0127(11) -0.0290(13) -0.0135(11) O2 0.0259(13) 0.0179(11) 0.0305(13) 0.0069(9) -0.0122(11) -0.0033(10) O3 0.0253(13) 0.0240(12) 0.0583(17) 0.0090(11) -0.0254(13) -0.0072(11) O4 0.0332(15) 0.0322(13) 0.0726(18) 0.0257(13) -0.0376(14) -0.0180(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O2 2.270(2) 2_675 ? Cd1 O2 2.285(2) 1_545 ? Cd1 N6 2.330(3) . ? Cd1 N5 2.331(3) . ? Cd1 O1 2.367(2) . ? Cd1 N1 2.373(3) . ? Cd1 C1 2.739(3) . ? Cd1 Cd1 3.6659(6) 2_665 ? C1 O1 1.288(3) . ? C1 N1 1.317(4) . ? C1 C3 1.462(4) . ? C2 O3 1.249(3) . ? C2 N2 1.345(4) . ? C2 C4 1.472(4) . ? C3 C5 1.385(4) . ? C3 C4 1.418(4) . ? C4 C6 1.386(4) . ? C5 C7 1.390(4) . ? C5 H5 0.9300 . ? C6 C8 1.393(4) . ? C6 H6 0.9300 . ? C7 C8 1.407(4) . ? C7 C9 1.471(4) . ? C8 C10 1.467(4) . ? C9 O4 1.246(3) . ? C9 N3 1.347(4) . ? C10 N4 1.299(4) . ? C10 O2 1.320(3) . ? C11 N5 1.319(4) . ? C11 C12 1.398(5) . ? C11 H11 0.9300 . ? C12 C13 1.360(6) . ? C12 H12 0.9300 . ? C13 C14 1.401(6) . ? C13 H13 0.9300 . ? C14 C15 1.418(5) . ? C14 C22 1.432(6) . ? C15 N5 1.350(4) . ? C15 C16 1.440(5) . ? C16 N6 1.375(4) . ? C16 C20 1.405(5) . ? C17 N6 1.327(4) . ? C17 C18 1.390(5) . ? C17 H17 0.9300 . ? C18 C19 1.372(6) . ? C18 H18 0.9300 . ? C19 C20 1.402(5) . ? C19 H19 0.9300 . ? C20 C21 1.440(5) . ? C21 C22 1.333(6) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? N1 N2 1.395(3) . ? N2 H2 0.8600 . ? N3 N4 1.392(3) . ? N3 H3 0.8600 . ? O2 Cd1 2.270(2) 2_675 ? O2 Cd1 2.285(2) 1_565 ? 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 Cd1 O2 72.85(8) 2_675 1_545 ? O2 Cd1 N6 108.20(9) 2_675 . ? O2 Cd1 N6 102.81(9) 1_545 . ? O2 Cd1 N5 157.16(8) 2_675 . ? O2 Cd1 N5 84.66(8) 1_545 . ? N6 Cd1 N5 72.39(10) . . ? O2 Cd1 O1 95.00(8) 2_675 . ? O2 Cd1 O1 106.31(8) 1_545 . ? N6 Cd1 O1 147.03(9) . . ? N5 Cd1 O1 95.12(9) . . ? O2 Cd1 N1 84.72(8) 2_675 . ? O2 Cd1 N1 150.56(9) 1_545 . ? N6 Cd1 N1 102.18(9) . . ? N5 Cd1 N1 117.82(9) . . ? O1 Cd1 N1 56.02(8) . . ? O2 Cd1 C1 85.26(8) 2_675 . ? O2 Cd1 C1 127.67(9) 1_545 . ? N6 Cd1 C1 129.31(10) . . ? N5 Cd1 C1 112.49(9) . . ? O1 Cd1 C1 28.03(8) . . ? N1 Cd1 C1 28.72(9) . . ? O2 Cd1 Cd1 36.56(5) 2_675 2_665 ? O2 Cd1 Cd1 36.29(5) 1_545 2_665 ? N6 Cd1 Cd1 109.37(7) . 2_665 ? N5 Cd1 Cd1 120.85(7) . 2_665 ? O1 Cd1 Cd1 103.24(6) . 2_665 ? N1 Cd1 Cd1 119.07(7) . 2_665 ? C1 Cd1 Cd1 109.25(7) . 2_665 ? O1 C1 N1 117.4(3) . . ? O1 C1 C3 122.1(3) . . ? N1 C1 C3 120.4(3) . . ? O1 C1 Cd1 59.71(15) . . ? N1 C1 Cd1 60.00(16) . . ? C3 C1 Cd1 162.0(2) . . ? O3 C2 N2 121.8(3) . . ? O3 C2 C4 123.1(3) . . ? N2 C2 C4 115.2(3) . . ? C5 C3 C4 119.3(3) . . ? C5 C3 C1 121.4(3) . . ? C4 C3 C1 119.1(3) . . ? C6 C4 C3 120.5(3) . . ? C6 C4 C2 120.3(3) . . ? C3 C4 C2 119.1(3) . . ? C3 C5 C7 120.1(3) . . ? C3 C5 H5 119.9 . . ? C7 C5 H5 119.9 . . ? C4 C6 C8 120.0(3) . . ? C4 C6 H6 120.0 . . ? C8 C6 H6 120.0 . . ? C5 C7 C8 120.7(3) . . ? C5 C7 C9 120.3(3) . . ? C8 C7 C9 118.9(3) . . ? C6 C8 C7 119.3(3) . . ? C6 C8 C10 122.1(3) . . ? C7 C8 C10 118.5(3) . . ? O4 C9 N3 122.0(3) . . ? O4 C9 C7 123.4(3) . . ? N3 C9 C7 114.6(3) . . ? N4 C10 O2 118.4(3) . . ? N4 C10 C8 122.6(3) . . ? O2 C10 C8 119.0(3) . . ? N5 C11 C12 122.7(4) . . ? N5 C11 H11 118.7 . . ? C12 C11 H11 118.7 . . ? C13 C12 C11 118.7(4) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? C12 C13 C14 120.4(4) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 C15 117.1(4) . . ? C13 C14 C22 123.8(4) . . ? C15 C14 C22 119.1(4) . . ? N5 C15 C14 121.6(3) . . ? N5 C15 C16 119.0(3) . . ? C14 C15 C16 119.4(3) . . ? N6 C16 C20 121.6(3) . . ? N6 C16 C15 118.5(3) . . ? C20 C16 C15 119.9(3) . . ? N6 C17 C18 123.6(4) . . ? N6 C17 H17 118.2 . . ? C18 C17 H17 118.2 . . ? C19 C18 C17 118.4(4) . . ? C19 C18 H18 120.8 . . ? C17 C18 H18 120.8 . . ? C18 C19 C20 120.4(4) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C19 C20 C16 117.6(4) . . ? C19 C20 C21 123.8(4) . . ? C16 C20 C21 118.6(4) . . ? C22 C21 C20 122.0(4) . . ? C22 C21 H21 119.0 . . ? C20 C21 H21 119.0 . . ? C21 C22 C14 121.1(4) . . ? C21 C22 H22 119.5 . . ? C14 C22 H22 119.5 . . ? C1 N1 N2 119.0(3) . . ? C1 N1 Cd1 91.28(19) . . ? N2 N1 Cd1 143.61(19) . . ? C2 N2 N1 127.1(3) . . ? C2 N2 H2 116.5 . . ? N1 N2 H2 116.5 . . ? C9 N3 N4 128.7(3) . . ? C9 N3 H3 115.6 . . ? N4 N3 H3 115.6 . . ? C10 N4 N3 116.6(3) . . ? C11 N5 C15 119.4(3) . . ? C11 N5 Cd1 124.9(3) . . ? C15 N5 Cd1 114.7(2) . . ? C17 N6 C16 118.4(3) . . ? C17 N6 Cd1 127.1(3) . . ? C16 N6 Cd1 114.3(2) . . ? C1 O1 Cd1 92.25(18) . . ? C10 O2 Cd1 120.24(19) . 2_675 ? C10 O2 Cd1 129.70(18) . 1_565 ? Cd1 O2 Cd1 107.15(8) 2_675 1_565 ? 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 N2 H2 O4 0.86 1.94 2.802(3) 175.2 1_455 N3 H3 O3 0.86 1.95 2.810(3) 175.8 1_655 C13 H13 O4 0.93 2.50 3.358(5) 153.2 2_666 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.568 _refine_diff_density_min -0.749 _refine_diff_density_rms 0.119