# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 data_DG1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 N4 O9 Zn2' _chemical_formula_weight 539.07 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 8.5707(11) _cell_length_b 9.8985(12) _cell_length_c 14.2812(17) _cell_angle_alpha 104.986(5) _cell_angle_beta 102.291(5) _cell_angle_gamma 91.286(5) _cell_volume 1139.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 250 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.571 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 2.156 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8495 _exptl_absorpt_correction_T_max 0.9572 _exptl_absorpt_process_details ; 'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL SPACE EXPLORATION, Bruker Analytical X-ray Systems, 1997 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18286 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_unetI/netI 0.0293 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 27.60 _reflns_number_total 5241 _reflns_number_gt 4374 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART APEX II (Bruker,2010)' _computing_cell_refinement 'SMART APEX II' _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3v2 for windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2008)' _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^ > 2\s(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^)+(0.1031P)^2^+1.9734P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5241 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1803 _refine_ls_wR_factor_gt 0.1722 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _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 0.66780(5) 0.58387(4) 0.53828(3) 0.02952(17) Uani 1 1 d . . . Zn2 Zn 0.66305(6) 0.36064(5) 0.33879(3) 0.03533(17) Uani 1 1 d . . . O1 O 0.5117(3) 0.4709(3) 0.4006(2) 0.0306(6) Uani 1 1 d . . . O2 O 0.7819(4) 0.4013(3) 0.5564(2) 0.0413(7) Uani 1 1 d . . . O3 O 0.7767(4) 0.2413(3) 0.4132(2) 0.0426(7) Uani 1 1 d . . . N1 N 0.8291(4) 0.6954(4) 0.6736(3) 0.0400(8) Uani 1 1 d . . . O6 O 0.5849(4) 0.7728(3) 0.5243(2) 0.0413(7) Uani 1 1 d . . . O7 O 0.5058(5) 0.7191(3) 0.3593(3) 0.0569(10) Uani 1 1 d . . . C1 C 0.8203(5) 0.2895(4) 0.5071(3) 0.0344(8) Uani 1 1 d . . . C6 C 0.5083(6) 0.9570(4) 0.4501(3) 0.0412(10) Uani 1 1 d . . . H6A H 0.5977 0.9988 0.4326 0.049 Uiso 1 1 calc R . . H6B H 0.4123 0.9611 0.4010 0.049 Uiso 1 1 calc R . . C7 C 0.9087(7) 0.8138(7) 0.6778(4) 0.0624(16) Uani 1 1 d . . . H7 H 0.8914 0.8484 0.6221 0.075 Uiso 1 1 calc R . . C5 C 0.5347(6) 0.8042(4) 0.4438(3) 0.0385(9) Uani 1 1 d . . . C2 C 0.9255(6) 0.2024(5) 0.5622(4) 0.0427(10) Uani 1 1 d . . . H2A H 0.9860 0.1462 0.5184 0.051 Uiso 1 1 calc R . . H2B H 0.8591 0.1390 0.5820 0.051 Uiso 1 1 calc R . . C11 C 0.8562(7) 0.6481(6) 0.7552(4) 0.0563(13) Uani 1 1 d . . . H11 H 0.8017 0.5643 0.7523 0.068 Uiso 1 1 calc R . . N2 N 1.1523(8) 0.9040(7) 0.9458(5) 0.0794(16) Uani 1 1 d . . . C9 C 1.0423(7) 0.8396(8) 0.8472(4) 0.0693(18) Uani 1 1 d . . . C10 C 0.9604(9) 0.7176(7) 0.8425(4) 0.0713(18) Uani 1 1 d . . . H10 H 0.9750 0.6819 0.8977 0.086 Uiso 1 1 calc R . . N3 N 1.2119(9) 1.0031(7) 0.9404(5) 0.0861(18) Uani 1 1 d . . . C8 C 1.0195(8) 0.8888(8) 0.7654(5) 0.079(2) Uani 1 1 d . . . H8 H 1.0761 0.9708 0.7669 0.095 Uiso 1 1 calc R . . C12 C 1.3255(7) 1.0712(7) 1.0396(4) 0.0657(17) Uani 1 1 d . . . C13 C 1.3918(9) 1.1954(9) 1.0419(5) 0.083(2) Uani 1 1 d . . . H13 H 1.3665 1.2299 0.9863 0.100 Uiso 1 1 calc R . . C16 C 1.3629(9) 1.0238(7) 1.1216(5) 0.077(2) Uani 1 1 d . . . H16 H 1.3176 0.9376 1.1218 0.092 Uiso 1 1 calc R . . C15 C 1.4701(8) 1.1054(6) 1.2055(5) 0.0656(17) Uani 1 1 d . . . H15 H 1.4968 1.0717 1.2614 0.079 Uiso 1 1 calc R . . C14 C 1.4986(9) 1.2729(7) 1.1272(4) 0.0692(17) Uani 1 1 d . . . H14 H 1.5459 1.3584 1.1272 0.083 Uiso 1 1 calc R . . N4 N 1.5353(5) 1.2290(4) 1.2088(3) 0.0417(9) Uani 1 1 d . . . C4 C 1.1410(5) 0.4019(5) 0.6300(3) 0.0368(9) Uani 1 1 d . . . C3 C 1.0414(6) 0.2944(5) 0.6546(3) 0.0437(10) Uani 1 1 d . . . H3A H 0.9810 0.3418 0.7019 0.052 Uiso 1 1 calc R . . H3B H 1.1118 0.2353 0.6858 0.052 Uiso 1 1 calc R . . O4 O 1.1545(4) 0.3845(4) 0.5440(2) 0.0455(8) Uani 1 1 d . . . O5 O 1.2068(4) 0.5081(4) 0.7023(2) 0.0451(7) Uani 1 1 d . . . O1W O 1.2446(18) 0.4420(13) 0.8877(6) 0.179(4) Uani 1 1 d G . . H1WA H 1.1917 0.5031 0.8655 0.268 Uiso 1 1 d G . . H1WB H 1.2990 0.4019 0.8467 0.268 Uiso 1 1 d G . . O2W O 1.527(3) 0.293(2) 0.8322(16) 0.174(7) Uiso 0.50 1 d P . . O3W O 0.985(3) 0.276(2) 0.8955(16) 0.180(8) Uiso 0.50 1 d P . . 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 0.0270(3) 0.0268(3) 0.0260(3) -0.00173(17) -0.00158(18) -0.00222(17) Zn2 0.0314(3) 0.0354(3) 0.0276(3) -0.00552(19) -0.00042(19) -0.00020(19) O1 0.0284(13) 0.0272(13) 0.0300(13) 0.0008(10) 0.0020(11) 0.0000(10) O2 0.0362(16) 0.0410(16) 0.0387(16) 0.0017(13) 0.0017(13) 0.0072(13) O3 0.0395(17) 0.0402(16) 0.0376(16) -0.0001(13) -0.0007(13) 0.0036(13) N1 0.0317(18) 0.046(2) 0.0286(17) -0.0060(15) -0.0022(14) -0.0044(15) O6 0.0506(19) 0.0273(14) 0.0395(16) 0.0047(12) 0.0012(14) 0.0028(13) O7 0.091(3) 0.0342(17) 0.0383(18) 0.0063(14) 0.0045(18) 0.0063(17) C1 0.0267(18) 0.0314(19) 0.040(2) 0.0056(16) 0.0016(16) -0.0051(15) C6 0.052(3) 0.027(2) 0.044(2) 0.0111(17) 0.009(2) 0.0000(18) C7 0.061(3) 0.067(4) 0.041(3) -0.007(2) 0.003(2) -0.032(3) C5 0.043(2) 0.0270(19) 0.043(2) 0.0075(17) 0.0060(18) 0.0004(16) C2 0.042(2) 0.030(2) 0.051(3) 0.0122(19) 0.000(2) -0.0021(17) C11 0.060(3) 0.056(3) 0.037(2) 0.000(2) -0.008(2) 0.005(2) N2 0.086(4) 0.076(4) 0.072(4) 0.019(3) 0.014(3) 0.001(3) C9 0.047(3) 0.095(5) 0.039(3) -0.017(3) -0.005(2) 0.004(3) C10 0.075(4) 0.076(4) 0.040(3) -0.002(3) -0.015(3) 0.008(3) N3 0.095(5) 0.084(4) 0.074(4) 0.012(3) 0.021(3) -0.013(4) C8 0.064(4) 0.081(4) 0.064(4) -0.021(3) 0.008(3) -0.042(3) C12 0.046(3) 0.080(4) 0.042(3) -0.018(3) -0.009(2) -0.004(3) C13 0.085(5) 0.104(6) 0.038(3) 0.011(3) -0.022(3) -0.021(4) C16 0.078(4) 0.050(3) 0.075(4) -0.007(3) -0.010(3) -0.024(3) C15 0.072(4) 0.054(3) 0.052(3) 0.008(3) -0.017(3) -0.016(3) C14 0.080(4) 0.069(4) 0.042(3) 0.009(3) -0.012(3) -0.022(3) N4 0.040(2) 0.0403(19) 0.0298(17) -0.0071(15) -0.0038(15) -0.0033(16) C4 0.0276(19) 0.042(2) 0.035(2) 0.0066(17) -0.0010(16) 0.0012(16) C3 0.043(2) 0.046(2) 0.041(2) 0.019(2) 0.0001(19) 0.001(2) O4 0.0340(16) 0.062(2) 0.0330(16) 0.0059(14) 0.0024(12) -0.0107(14) O5 0.0434(18) 0.0485(18) 0.0352(16) 0.0012(14) 0.0046(13) -0.0055(14) O1W 0.259(13) 0.185(10) 0.069(4) 0.048(5) -0.025(6) -0.051(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 2.049(3) 2_666 ? Zn1 O6 2.057(3) . ? Zn1 O2 2.122(3) . ? Zn1 N1 2.135(3) . ? Zn1 O1 2.141(3) . ? Zn1 O4 2.175(3) 2_766 ? Zn1 Zn2 3.1131(7) . ? Zn1 Zn1 3.1197(9) 2_666 ? Zn2 O1 1.925(3) . ? Zn2 O3 1.933(3) . ? Zn2 O5 1.971(3) 2_766 ? Zn2 N4 2.040(3) 1_444 ? O1 Zn1 2.049(3) 2_666 ? O2 C1 1.241(5) . ? O3 C1 1.270(5) . ? N1 C7 1.324(7) . ? N1 C11 1.342(7) . ? O6 C5 1.258(5) . ? O7 C5 1.252(5) . ? C1 C2 1.503(6) . ? C6 C6 1.498(9) 2_676 ? C6 C5 1.517(6) . ? C7 C8 1.414(8) . ? C2 C3 1.529(6) . ? C11 C10 1.372(7) . ? N2 N3 1.123(9) . ? N2 C9 1.491(8) . ? C9 C8 1.357(11) . ? C9 C10 1.362(10) . ? N3 C12 1.517(8) . ? C12 C13 1.332(11) . ? C12 C16 1.351(11) . ? C13 C14 1.386(8) . ? C16 C15 1.389(8) . ? C15 N4 1.319(7) . ? C14 N4 1.326(7) . ? N4 Zn2 2.040(3) 1_666 ? C4 O4 1.226(5) . ? C4 O5 1.285(5) . ? C4 C3 1.505(6) . ? O4 Zn1 2.175(3) 2_766 ? O5 Zn2 1.971(3) 2_766 ? 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 O6 95.74(12) 2_666 . ? O1 Zn1 O2 90.03(12) 2_666 . ? O6 Zn1 O2 172.98(13) . . ? O1 Zn1 N1 97.69(13) 2_666 . ? O6 Zn1 N1 88.31(14) . . ? O2 Zn1 N1 86.95(14) . . ? O1 Zn1 O1 83.77(11) 2_666 . ? O6 Zn1 O1 92.23(11) . . ? O2 Zn1 O1 92.37(11) . . ? N1 Zn1 O1 178.38(13) . . ? O1 Zn1 O4 171.83(12) 2_666 2_766 ? O6 Zn1 O4 88.08(14) . 2_766 ? O2 Zn1 O4 86.71(14) . 2_766 ? N1 Zn1 O4 89.62(14) . 2_766 ? O1 Zn1 O4 88.87(11) . 2_766 ? O1 Zn1 Zn2 109.49(8) 2_666 . ? O6 Zn1 Zn2 115.30(9) . . ? O2 Zn1 Zn2 66.13(8) . . ? N1 Zn1 Zn2 140.94(11) . . ? O1 Zn1 Zn2 37.55(7) . . ? O4 Zn1 Zn2 62.34(9) 2_766 . ? O1 Zn1 Zn1 43.01(8) 2_666 2_666 ? O6 Zn1 Zn1 95.30(9) . 2_666 ? O2 Zn1 Zn1 91.65(9) . 2_666 ? N1 Zn1 Zn1 140.70(11) . 2_666 ? O1 Zn1 Zn1 40.76(8) . 2_666 ? O4 Zn1 Zn1 129.54(8) 2_766 2_666 ? Zn2 Zn1 Zn1 71.047(18) . 2_666 ? O1 Zn2 O3 115.33(13) . . ? O1 Zn2 O5 105.91(13) . 2_766 ? O3 Zn2 O5 117.16(15) . 2_766 ? O1 Zn2 N4 106.83(14) . 1_444 ? O3 Zn2 N4 105.85(15) . 1_444 ? O5 Zn2 N4 104.85(15) 2_766 1_444 ? O1 Zn2 Zn1 42.65(8) . . ? O3 Zn2 Zn1 89.30(9) . . ? O5 Zn2 Zn1 90.98(9) 2_766 . ? N4 Zn2 Zn1 149.22(12) 1_444 . ? Zn2 O1 Zn1 131.31(14) . 2_666 ? Zn2 O1 Zn1 99.79(12) . . ? Zn1 O1 Zn1 96.23(11) 2_666 . ? C1 O2 Zn1 141.1(3) . . ? C1 O3 Zn2 117.7(3) . . ? C7 N1 C11 118.1(4) . . ? C7 N1 Zn1 119.6(4) . . ? C11 N1 Zn1 122.2(3) . . ? C5 O6 Zn1 125.9(3) . . ? O2 C1 O3 125.3(4) . . ? O2 C1 C2 117.9(4) . . ? O3 C1 C2 116.8(4) . . ? C6 C6 C5 114.7(5) 2_676 . ? N1 C7 C8 121.2(6) . . ? O7 C5 O6 124.9(4) . . ? O7 C5 C6 117.7(4) . . ? O6 C5 C6 117.3(4) . . ? C1 C2 C3 111.4(4) . . ? N1 C11 C10 123.1(6) . . ? N3 N2 C9 106.9(7) . . ? C8 C9 C10 119.3(5) . . ? C8 C9 N2 127.0(7) . . ? C10 C9 N2 113.7(6) . . ? C9 C10 C11 119.0(6) . . ? N2 N3 C12 108.3(7) . . ? C9 C8 C7 119.3(6) . . ? C13 C12 C16 119.0(5) . . ? C13 C12 N3 112.0(6) . . ? C16 C12 N3 129.0(6) . . ? C12 C13 C14 119.9(6) . . ? C12 C16 C15 119.1(6) . . ? N4 C15 C16 122.4(6) . . ? N4 C14 C13 122.0(6) . . ? C15 N4 C14 117.6(4) . . ? C15 N4 Zn2 121.7(4) . 1_666 ? C14 N4 Zn2 120.2(4) . 1_666 ? O4 C4 O5 124.0(4) . . ? O4 C4 C3 119.2(4) . . ? O5 C4 C3 116.8(4) . . ? C4 C3 C2 112.2(4) . . ? C4 O4 Zn1 140.1(3) . 2_766 ? C4 O5 Zn2 112.9(3) . 2_766 ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.505 _refine_diff_density_min -0.604 _refine_diff_density_rms 0.160 _database_code_depnum_ccdc_archive 'CCDC 974221' data_DG2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 N2 O6 Zn' _chemical_formula_weight 321.59 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 5.23330(10) _cell_length_b 9.1580(3) _cell_length_c 14.8415(4) _cell_angle_alpha 84.1910(10) _cell_angle_beta 85.964(2) _cell_angle_gamma 79.8480(10) _cell_volume 695.57(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 250 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 1.788 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8946 _exptl_absorpt_correction_T_max 0.9753 _exptl_absorpt_process_details ; 'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL SPACE EXPLORATION, Bruker Analytical X-ray Systems, 1997 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11953 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 27.58 _reflns_number_total 3198 _reflns_number_gt 3016 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART APEX II (Bruker,2010)' _computing_cell_refinement 'SMART APEX II' _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3v2 for windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2008)' _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^ > 2\s(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^)+(0.0780P)^2^+0.6584P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3198 _refine_ls_number_parameters 171 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1373 _refine_ls_wR_factor_gt 0.1361 _refine_ls_goodness_of_fit_ref 1.220 _refine_ls_restrained_S_all 1.220 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5943(6) 0.3822(3) 0.6266(2) 0.0297(6) Uani 1 1 d . . . C2 C 0.5226(7) 0.2416(4) 0.5995(2) 0.0335(7) Uani 1 1 d . . . H2A H 0.6769 0.1654 0.5996 0.040 Uiso 1 1 calc R . . H2B H 0.4666 0.2599 0.5378 0.040 Uiso 1 1 calc R . . C3 C 0.3116(6) 0.1821(4) 0.6591(3) 0.0361(7) Uani 1 1 d . . . H3A H 0.1504 0.2525 0.6536 0.043 Uiso 1 1 calc R . . H3B H 0.3576 0.1733 0.7219 0.043 Uiso 1 1 calc R . . C4 C 0.2689(6) 0.0308(3) 0.6348(3) 0.0372(7) Uani 1 1 d . . . H4A H 0.1055 0.0105 0.6640 0.045 Uiso 1 1 calc R . . H4B H 0.2525 0.0362 0.5698 0.045 Uiso 1 1 calc R . . C5 C 0.4818(6) -0.0986(3) 0.6613(2) 0.0281(6) Uani 1 1 d . . . C8 C 1.0724(7) 0.6735(4) 0.8022(2) 0.0371(7) Uani 1 1 d . . . H8 H 1.0500 0.7684 0.7718 0.044 Uiso 1 1 calc R . . C9 C 0.9695(7) 0.4383(4) 0.8219(2) 0.0371(7) Uani 1 1 d . . . H9 H 0.8760 0.3688 0.8051 0.044 Uiso 1 1 calc R . . C10 C 1.1323(8) 0.3978(4) 0.8927(3) 0.0424(8) Uani 1 1 d . . . H10 H 1.1485 0.3030 0.9231 0.051 Uiso 1 1 calc R . . C11 C 1.2710(7) 0.5013(4) 0.9176(2) 0.0377(7) Uani 1 1 d . . . C12 C 1.2401(8) 0.6414(5) 0.8720(3) 0.0424(8) Uani 1 1 d . . . H12 H 1.3305 0.7129 0.8879 0.051 Uiso 1 1 calc R . . N1 N 0.9408(5) 0.5733(3) 0.77643(17) 0.0297(5) Uani 1 1 d . . . N2 N 1.4398(7) 0.4530(4) 0.9903(2) 0.0473(8) Uani 1 1 d . . . O1 O 0.7525(5) 0.4467(3) 0.57480(18) 0.0398(6) Uani 1 1 d . . . O2 O 0.5078(6) 0.4351(3) 0.69824(19) 0.0467(6) Uani 1 1 d . . . O1W O 1.0324(5) 0.6923(3) 0.57304(17) 0.0388(6) Uani 1 1 d . . . O3 O 0.6638(5) -0.0849(3) 0.7052(2) 0.0494(7) Uani 1 1 d . . . O2W O 1.497(4) 0.003(3) 0.9196(15) 0.213(8) Uiso 0.50 1 d P . . O4 O 0.4561(4) -0.2248(2) 0.63524(17) 0.0330(5) Uani 1 1 d . . . O3W O 1.191(4) -0.011(3) 1.0003(17) 0.225(9) Uiso 0.50 1 d P . . Zn1 Zn 0.75352(6) 0.61627(4) 0.65761(2) 0.02654(15) Uani 1 1 d . . . H2WB H 1.1680 0.7201 0.5954 0.050 Uiso 1 1 d . . . H1WA H 1.1046 0.6408 0.5224 0.050 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0271(14) 0.0233(13) 0.0393(16) -0.0026(12) -0.0086(12) -0.0035(11) C2 0.0392(16) 0.0285(15) 0.0358(16) -0.0073(12) 0.0009(13) -0.0126(13) C3 0.0293(15) 0.0248(15) 0.053(2) -0.0039(13) 0.0031(14) -0.0035(12) C4 0.0270(15) 0.0249(15) 0.061(2) -0.0013(14) -0.0075(14) -0.0065(12) C5 0.0264(13) 0.0231(13) 0.0351(15) -0.0018(11) -0.0006(11) -0.0062(11) C8 0.0399(17) 0.0356(17) 0.0364(16) 0.0013(13) -0.0098(13) -0.0081(14) C9 0.0396(17) 0.0355(17) 0.0364(16) -0.0016(13) -0.0072(13) -0.0059(13) C10 0.051(2) 0.0379(18) 0.0372(18) 0.0041(14) -0.0103(15) -0.0041(15) C11 0.0339(16) 0.0483(19) 0.0285(15) -0.0021(13) -0.0081(12) 0.0009(14) C12 0.0451(19) 0.045(2) 0.0399(18) -0.0020(15) -0.0161(15) -0.0102(16) N1 0.0284(12) 0.0343(13) 0.0261(12) -0.0031(10) -0.0037(9) -0.0031(10) N2 0.0494(18) 0.054(2) 0.0375(16) 0.0018(14) -0.0189(14) -0.0025(15) O1 0.0400(13) 0.0337(12) 0.0496(14) -0.0101(10) 0.0049(11) -0.0165(10) O2 0.0574(16) 0.0414(14) 0.0468(14) -0.0193(12) 0.0059(12) -0.0181(12) O1W 0.0320(11) 0.0497(14) 0.0406(13) -0.0133(11) 0.0036(10) -0.0199(11) O3 0.0457(15) 0.0359(13) 0.0698(19) -0.0087(12) -0.0289(14) -0.0031(11) O4 0.0273(10) 0.0258(10) 0.0475(13) -0.0067(9) -0.0045(9) -0.0056(8) Zn1 0.0268(2) 0.0256(2) 0.0284(2) -0.00468(13) -0.00489(13) -0.00503(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.237(4) . ? C1 O1 1.271(4) . ? C1 C2 1.503(4) . ? C1 Zn1 2.527(3) . ? C2 C3 1.509(4) . ? C3 C4 1.524(5) . ? C4 C5 1.518(4) . ? C5 O3 1.222(4) . ? C5 O4 1.286(4) . ? C8 N1 1.339(4) . ? C8 C12 1.380(5) . ? C9 N1 1.337(4) . ? C9 C10 1.380(5) . ? C10 C11 1.383(5) . ? C11 C12 1.377(5) . ? C11 N2 1.428(4) . ? N1 Zn1 2.047(3) . ? N2 N2 1.220(7) 2_867 ? O1 Zn1 2.077(2) . ? O2 Zn1 2.283(3) . ? O1W Zn1 2.028(2) . ? O4 Zn1 1.957(2) 1_545 ? Zn1 O4 1.957(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 C1 O1 119.3(3) . . ? O2 C1 C2 122.0(3) . . ? O1 C1 C2 118.7(3) . . ? O2 C1 Zn1 64.36(18) . . ? O1 C1 Zn1 54.97(16) . . ? C2 C1 Zn1 173.5(2) . . ? C1 C2 C3 115.1(3) . . ? C2 C3 C4 112.6(3) . . ? C5 C4 C3 115.0(3) . . ? O3 C5 O4 122.1(3) . . ? O3 C5 C4 122.6(3) . . ? O4 C5 C4 115.3(3) . . ? N1 C8 C12 122.6(3) . . ? N1 C9 C10 122.6(3) . . ? C9 C10 C11 118.6(3) . . ? C12 C11 C10 119.2(3) . . ? C12 C11 N2 124.4(3) . . ? C10 C11 N2 116.3(3) . . ? C11 C12 C8 118.7(3) . . ? C9 N1 C8 118.3(3) . . ? C9 N1 Zn1 121.2(2) . . ? C8 N1 Zn1 119.7(2) . . ? N2 N2 C11 114.3(4) 2_867 . ? C1 O1 Zn1 95.0(2) . . ? C1 O2 Zn1 86.4(2) . . ? C5 O4 Zn1 114.26(19) . 1_545 ? O4 Zn1 O1W 101.08(11) 1_565 . ? O4 Zn1 N1 124.47(10) 1_565 . ? O1W Zn1 N1 100.68(10) . . ? O4 Zn1 O1 110.37(10) 1_565 . ? O1W Zn1 O1 89.48(10) . . ? N1 Zn1 O1 120.26(11) . . ? O4 Zn1 O2 94.89(10) 1_565 . ? O1W Zn1 O2 148.43(10) . . ? N1 Zn1 O2 92.20(11) . . ? O1 Zn1 O2 59.32(9) . . ? O4 Zn1 C1 104.32(9) 1_565 . ? O1W Zn1 C1 119.42(10) . . ? N1 Zn1 C1 107.99(11) . . ? O1 Zn1 C1 30.07(10) . . ? O2 Zn1 C1 29.25(10) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.439 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.168 _database_code_depnum_ccdc_archive 'CCDC 974222' data_DG3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H18 N8 O9 Zn2' _chemical_formula_weight 741.24 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 10.9188(4) _cell_length_b 11.5059(4) _cell_length_c 13.0695(4) _cell_angle_alpha 109.415(2) _cell_angle_beta 95.197(2) _cell_angle_gamma 97.024(2) _cell_volume 1521.76(9) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 250 _cell_measurement_theta_min 1.67 _cell_measurement_theta_max 27.57 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.618 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 1.643 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8257 _exptl_absorpt_correction_T_max 0.9648 _exptl_absorpt_process_details ; 'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL SPACE EXPLORATION, Bruker Analytical X-ray Systems, 1997 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25709 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_UnetI/netI 0.0303 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.57 _reflns_number_total 6979 _reflns_number_gt 5710 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART APEX II (Bruker,2010)' _computing_cell_refinement 'SMART APEX II' _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3v2 for windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2008)' _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^ > 2\s(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^)+(0.0602P)^2^+1.5347P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6979 _refine_ls_number_parameters 471 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1209 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4112(3) 0.1152(3) 0.7465(3) 0.0473(7) Uani 1 1 d . . . C5 C -0.0111(3) -0.3712(5) 0.9361(4) 0.0628(11) Uani 1 1 d . . . C6 C -0.0006(4) -0.4540(6) 1.0027(6) 0.111(2) Uani 1 1 d . . . H6 H 0.0080 -0.4047 1.0764 0.133 Uiso 1 1 calc R . . C7 C 0.5185(3) 0.5154(3) 0.5520(3) 0.0450(7) Uani 1 1 d . . . H7 H 0.5346 0.5997 0.5949 0.054 Uiso 1 1 calc R . . C8 C 0.5363(3) 0.4221(3) 0.6055(3) 0.0424(7) Uani 1 1 d . . . C9 C 0.6536(3) 0.3142(3) 0.9648(3) 0.0453(7) Uani 1 1 d . . . H9 H 0.6380 0.2278 0.9310 0.054 Uiso 1 1 calc R . . C10 C 0.6933(3) 0.3628(3) 1.0753(3) 0.0447(7) Uani 1 1 d . . . H10 H 0.7054 0.3109 1.1155 0.054 Uiso 1 1 calc R . . C11 C 0.7150(3) 0.4907(3) 1.1251(2) 0.0390(6) Uani 1 1 d . . . C12 C 0.6970(3) 0.5653(3) 1.0633(3) 0.0490(8) Uani 1 1 d . . . H12 H 0.7119 0.6519 1.0953 0.059 Uiso 1 1 calc R . . C13 C 0.6568(3) 0.5084(3) 0.9536(3) 0.0457(7) Uani 1 1 d . . . H13 H 0.6431 0.5583 0.9119 0.055 Uiso 1 1 calc R . . C14 C 0.7877(3) 0.5466(3) 1.4078(3) 0.0447(7) Uani 1 1 d . . . C15 C 0.8187(3) 0.4707(3) 1.4644(3) 0.0518(8) Uani 1 1 d . . . H15 H 0.8088 0.3846 1.4298 0.062 Uiso 1 1 calc R . . C16 C 0.8649(3) 0.5258(3) 1.5740(3) 0.0474(7) Uani 1 1 d . . . H16 H 0.8869 0.4749 1.6127 0.057 Uiso 1 1 calc R . . C17 C 0.8454(3) 0.7203(3) 1.5715(3) 0.0509(8) Uani 1 1 d . . . H17 H 0.8527 0.8057 1.6086 0.061 Uiso 1 1 calc R . . C18 C 0.8000(3) 0.6736(3) 1.4616(3) 0.0503(8) Uani 1 1 d . . . H18 H 0.7781 0.7262 1.4247 0.060 Uiso 1 1 calc R . . C19 C -0.2962(3) -0.2352(3) 0.8378(3) 0.0481(7) Uani 1 1 d . . . H19 H -0.3127 -0.3201 0.7968 0.058 Uiso 1 1 calc R . . C20 C -0.3915(3) -0.1777(4) 0.8844(4) 0.0652(11) Uani 1 1 d . . . H20 H -0.4709 -0.2229 0.8748 0.078 Uiso 1 1 calc R . . C21 C -0.3664(4) -0.0519(4) 0.9453(3) 0.0583(10) Uani 1 1 d . . . C22 C -0.2497(4) 0.0121(4) 0.9562(3) 0.0567(9) Uani 1 1 d . . . H22 H -0.2312 0.0973 0.9957 0.068 Uiso 1 1 calc R . . C23 C -0.1610(3) -0.0512(3) 0.9081(3) 0.0467(7) Uani 1 1 d . . . H23 H -0.0813 -0.0071 0.9164 0.056 Uiso 1 1 calc R . . C24 C 0.7354(10) 0.1827(12) 0.5744(7) 0.089(4) Uani 0.50 1 d P . . C24A C 0.6877(6) 0.1013(6) 0.5900(6) 0.0427(14) Uani 0.50 1 d P . . C25 C 0.8267(12) 0.1162(14) 0.5276(7) 0.100(5) Uani 0.50 1 d P . . C25A C 0.7799(7) 0.0412(6) 0.5416(7) 0.0486(17) Uani 0.50 1 d P . . C26 C 0.9081(3) 0.0989(3) 0.5824(3) 0.0565(9) Uani 1 1 d . . . C27 C 0.9303(6) 0.2199(7) 0.6536(6) 0.0507(16) Uani 0.50 1 d P . . C27A C 0.9064(8) 0.1273(9) 0.7045(6) 0.066(2) Uani 0.50 1 d P . . C28 C 0.8312(5) 0.2729(5) 0.6975(5) 0.0396(13) Uani 0.50 1 d P . . C28A C 0.8105(7) 0.1877(8) 0.7424(6) 0.0569(18) Uani 0.50 1 d P . . N1 N 0.6360(2) 0.3843(2) 0.90331(19) 0.0357(5) Uani 1 1 d . . . N2 N 0.7641(3) 0.5517(3) 1.2389(2) 0.0459(6) Uani 1 1 d . . . N3 N 0.7371(3) 0.4874(3) 1.2945(2) 0.0500(7) Uani 1 1 d . . . N4 N 0.8795(2) 0.6487(2) 1.6273(2) 0.0415(6) Uani 1 1 d . . . N5 N -0.1814(2) -0.1735(2) 0.84954(19) 0.0345(5) Uani 1 1 d . . . N6 N -0.4559(4) 0.0350(3) 1.0067(3) 0.0696(10) Uani 1 1 d . . . N7 N 1.0133(3) 0.0433(3) 0.5404(3) 0.0762(11) Uani 1 1 d . . . N8 N 0.7185(2) 0.2165(2) 0.6728(2) 0.0391(5) Uani 1 1 d . . . O1 O 0.4087(2) 0.2170(2) 0.7299(2) 0.0629(7) Uani 1 1 d . . . O2 O 0.5067(2) 0.0743(2) 0.7619(2) 0.0633(7) Uani 1 1 d . . . O1W O 0.3822(7) 0.1360(6) 0.3550(5) 0.173(3) Uani 1 1 d G . . H1WA H 0.4031 0.1512 0.4230 0.259 Uiso 1 1 d G . . H1WB H 0.3907 0.0616 0.3191 0.259 Uiso 1 1 d G . . O5 O -0.0514(3) -0.4225(3) 0.8355(3) 0.0690(8) Uani 1 1 d . . . O6 O 0.0209(3) -0.2593(3) 0.9796(3) 0.0832(9) Uani 1 1 d . . . O7 O 0.5139(3) 0.3091(2) 0.5531(2) 0.0634(7) Uani 1 1 d . . . O8 O 0.5751(2) 0.4634(2) 0.70705(19) 0.0507(6) Uani 1 1 d . . . Zn1 Zn 0.57508(3) 0.30221(3) 0.73547(3) 0.03334(10) Uani 1 1 d . . . Zn2 Zn -0.04095(3) -0.26868(3) 0.79043(3) 0.03629(11) Uani 1 1 d . . . C3 C 0.2692(3) -0.0604(3) 0.7597(3) 0.0496(8) Uani 1 1 d . . . C2 C 0.2862(3) 0.0489(4) 0.7506(3) 0.0540(8) Uani 1 1 d . . . C4 C 0.1451(3) -0.1253(3) 0.7661(3) 0.0546(9) Uani 1 1 d . . . O3 O 0.1404(3) -0.2283(3) 0.7772(3) 0.0778(9) Uani 1 1 d . . . O4 O 0.0515(3) -0.0782(3) 0.7626(4) 0.1130(16) Uani 1 1 d . . . H3 H 0.343(5) -0.101(4) 0.763(4) 0.088(15) Uiso 1 1 d . . . H2 H 0.217(5) 0.099(5) 0.743(5) 0.12(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 C1 0.0498(18) 0.0473(17) 0.0389(17) 0.0104(14) 0.0105(14) -0.0043(14) C5 0.0366(17) 0.088(3) 0.090(3) 0.066(3) 0.0085(18) 0.0087(18) C6 0.050(2) 0.156(6) 0.196(6) 0.153(6) 0.017(3) 0.018(3) C7 0.0478(17) 0.0437(16) 0.0500(18) 0.0261(15) 0.0012(14) 0.0076(13) C8 0.0385(15) 0.0475(17) 0.0488(18) 0.0277(15) 0.0025(13) 0.0067(13) C9 0.0615(19) 0.0340(14) 0.0395(17) 0.0143(13) -0.0006(14) 0.0058(13) C10 0.0567(18) 0.0427(16) 0.0363(16) 0.0187(13) -0.0009(14) 0.0054(14) C11 0.0359(14) 0.0460(16) 0.0332(15) 0.0110(12) 0.0072(11) 0.0059(12) C12 0.068(2) 0.0368(15) 0.0401(17) 0.0094(13) 0.0092(15) 0.0114(15) C13 0.066(2) 0.0377(15) 0.0386(16) 0.0172(13) 0.0115(15) 0.0145(14) C14 0.0444(16) 0.0523(18) 0.0327(15) 0.0086(13) 0.0100(13) 0.0047(14) C15 0.067(2) 0.0449(17) 0.0413(18) 0.0093(15) 0.0102(16) 0.0132(16) C16 0.0580(19) 0.0470(17) 0.0377(16) 0.0135(14) 0.0063(14) 0.0141(15) C17 0.066(2) 0.0420(17) 0.0432(18) 0.0123(14) 0.0056(16) 0.0105(15) C18 0.061(2) 0.0526(19) 0.0412(18) 0.0212(15) 0.0053(15) 0.0118(16) C19 0.0456(17) 0.0475(17) 0.055(2) 0.0226(15) 0.0128(15) 0.0043(14) C20 0.0406(18) 0.097(3) 0.079(3) 0.052(3) 0.0236(18) 0.0143(19) C21 0.077(3) 0.077(3) 0.0414(18) 0.0309(18) 0.0249(17) 0.046(2) C22 0.066(2) 0.057(2) 0.0438(19) 0.0077(16) 0.0044(16) 0.0276(18) C23 0.0481(17) 0.0407(16) 0.0443(17) 0.0067(14) -0.0012(14) 0.0097(13) C24 0.100(7) 0.147(10) 0.037(4) 0.029(5) 0.014(4) 0.084(8) C24A 0.041(3) 0.034(3) 0.046(4) 0.004(3) 0.013(3) 0.005(2) C25 0.111(9) 0.174(13) 0.025(4) 0.020(6) 0.017(5) 0.095(9) C25A 0.061(4) 0.038(3) 0.046(4) 0.009(3) 0.022(3) 0.009(3) C26 0.0521(19) 0.053(2) 0.063(2) 0.0111(17) 0.0272(18) 0.0132(16) C27 0.038(3) 0.051(4) 0.055(4) 0.006(3) 0.017(3) 0.010(3) C27A 0.065(5) 0.091(6) 0.047(4) 0.020(4) 0.015(4) 0.034(4) C28 0.033(3) 0.035(3) 0.045(3) 0.005(2) 0.010(2) 0.006(2) C28A 0.057(4) 0.077(5) 0.041(4) 0.018(4) 0.012(3) 0.029(4) N1 0.0426(12) 0.0356(12) 0.0319(12) 0.0142(10) 0.0075(10) 0.0089(10) N2 0.0511(15) 0.0506(15) 0.0339(13) 0.0114(12) 0.0071(11) 0.0093(12) N3 0.0537(16) 0.0560(16) 0.0370(14) 0.0133(13) 0.0068(12) 0.0042(13) N4 0.0442(13) 0.0440(14) 0.0355(13) 0.0110(11) 0.0081(11) 0.0104(11) N5 0.0383(12) 0.0363(12) 0.0310(12) 0.0135(10) 0.0062(10) 0.0075(10) N6 0.085(2) 0.059(2) 0.061(2) 0.0335(17) -0.0167(18) -0.0163(16) N7 0.060(2) 0.069(2) 0.082(3) -0.0043(17) 0.0270(19) 0.0197(18) N8 0.0456(13) 0.0362(12) 0.0386(13) 0.0130(11) 0.0157(11) 0.0115(10) O1 0.0539(14) 0.0564(15) 0.0801(19) 0.0310(14) 0.0094(13) -0.0053(12) O2 0.0516(14) 0.0560(15) 0.0777(19) 0.0196(14) 0.0132(13) -0.0016(12) O1W 0.187(5) 0.147(5) 0.125(4) -0.034(3) -0.045(4) 0.087(4) O5 0.0635(17) 0.0576(16) 0.094(2) 0.0402(16) 0.0067(16) 0.0057(13) O6 0.081(2) 0.085(2) 0.095(2) 0.051(2) 0.0022(18) 0.0089(18) O7 0.0882(19) 0.0463(14) 0.0568(16) 0.0253(12) -0.0130(14) 0.0110(13) O8 0.0680(15) 0.0451(12) 0.0431(13) 0.0240(10) -0.0015(11) 0.0063(11) Zn1 0.03830(18) 0.03284(17) 0.03303(18) 0.01463(14) 0.00938(13) 0.00892(13) Zn2 0.03640(18) 0.03900(19) 0.03725(19) 0.01627(15) 0.00894(14) 0.00878(14) C3 0.0438(17) 0.060(2) 0.0429(18) 0.0202(16) 0.0050(14) -0.0074(15) C2 0.0474(18) 0.0519(19) 0.059(2) 0.0176(17) 0.0111(16) -0.0024(15) C4 0.053(2) 0.058(2) 0.0410(18) 0.0094(15) 0.0108(15) -0.0172(16) O3 0.0692(18) 0.085(2) 0.083(2) 0.0546(18) -0.0131(15) -0.0260(15) O4 0.0536(17) 0.0601(18) 0.201(4) 0.010(2) 0.052(2) -0.0040(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.223(4) . ? C1 O1 1.262(4) . ? C1 C2 1.494(4) . ? C5 O6 1.213(6) . ? C5 O5 1.260(5) . ? C5 C6 1.495(5) . ? C5 Zn2 2.569(4) . ? C6 C6 1.040(10) 2_547 ? C7 C7 1.295(7) 2_666 ? C7 C8 1.486(4) . ? C8 O7 1.232(4) . ? C8 O8 1.263(4) . ? C8 Zn1 2.557(3) . ? C9 N1 1.332(4) . ? C9 C10 1.370(4) . ? C10 C11 1.377(4) . ? C11 C12 1.379(4) . ? C11 N2 1.435(4) . ? C12 C13 1.367(5) . ? C13 N1 1.339(4) . ? C14 C15 1.372(5) . ? C14 C18 1.378(5) . ? C14 N3 1.432(4) . ? C15 C16 1.376(5) . ? C16 N4 1.334(4) . ? C17 N4 1.332(4) . ? C17 C18 1.375(5) . ? C19 N5 1.332(4) . ? C19 C20 1.381(5) . ? C20 C21 1.379(6) . ? C21 C22 1.362(6) . ? C21 N6 1.564(5) . ? C22 C23 1.358(5) . ? C23 N5 1.338(4) . ? C24 C24A 1.102(14) . ? C24 N8 1.252(8) . ? C24 C25 1.392(11) . ? C24 C25A 1.684(12) . ? C24 C28 1.755(12) . ? C24A C25A 1.373(9) . ? C24A N8 1.383(7) . ? C24A C25 1.803(14) . ? C25 C25A 1.027(15) . ? C25 C26 1.169(10) . ? C25 C27 1.855(14) . ? C25A C26 1.445(9) . ? C26 C27 1.370(8) . ? C26 N7 1.446(4) . ? C26 C27A 1.521(8) . ? C27 C28 1.383(8) . ? C27 C27A 1.443(11) . ? C27 C28A 1.908(10) . ? C27A C28A 1.367(10) . ? C27A C28 1.979(10) . ? C28 N8 1.278(6) . ? C28 C28A 1.308(10) . ? C28A N8 1.435(7) . ? N1 Zn1 2.086(2) . ? N2 N3 1.227(4) . ? N4 Zn2 2.078(3) 1_666 ? N5 Zn2 2.052(2) . ? N6 N6 1.137(6) 2_457 ? N7 N7 1.169(7) 2_756 ? N8 Zn1 2.042(2) . ? O1 Zn1 1.939(2) . ? O5 Zn2 2.037(3) . ? O6 Zn2 2.466(3) . ? O7 Zn1 2.446(3) . ? O8 Zn1 2.009(2) . ? Zn2 O3 2.014(3) . ? Zn2 N4 2.078(3) 1_444 ? Zn2 O4 2.452(4) . ? Zn2 C4 2.568(3) . ? C3 C2 1.295(5) . ? C3 C4 1.488(4) . ? C4 O4 1.219(5) . ? C4 O3 1.236(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 C1 O1 124.0(3) . . ? O2 C1 C2 121.5(3) . . ? O1 C1 C2 114.4(3) . . ? O6 C5 O5 122.8(4) . . ? O6 C5 C6 119.6(5) . . ? O5 C5 C6 117.6(5) . . ? O6 C5 Zn2 71.4(2) . . ? O5 C5 Zn2 51.42(17) . . ? C6 C5 Zn2 169.0(5) . . ? C6 C6 C5 143.5(11) 2_547 . ? C7 C7 C8 122.9(4) 2_666 . ? O7 C8 O8 121.4(3) . . ? O7 C8 C7 121.4(3) . . ? O8 C8 C7 117.2(3) . . ? O7 C8 Zn1 70.81(17) . . ? O8 C8 Zn1 50.63(14) . . ? C7 C8 Zn1 167.7(3) . . ? N1 C9 C10 123.4(3) . . ? C9 C10 C11 118.1(3) . . ? C10 C11 C12 119.6(3) . . ? C10 C11 N2 122.8(3) . . ? C12 C11 N2 117.5(3) . . ? C13 C12 C11 118.1(3) . . ? N1 C13 C12 123.2(3) . . ? C15 C14 C18 119.9(3) . . ? C15 C14 N3 117.2(3) . . ? C18 C14 N3 122.8(3) . . ? C14 C15 C16 118.0(3) . . ? N4 C16 C15 123.1(3) . . ? N4 C17 C18 123.0(3) . . ? C17 C18 C14 118.0(3) . . ? N5 C19 C20 122.3(3) . . ? C21 C20 C19 118.6(4) . . ? C22 C21 C20 119.3(3) . . ? C22 C21 N6 111.7(3) . . ? C20 C21 N6 129.1(4) . . ? C23 C22 C21 118.5(4) . . ? N5 C23 C22 123.8(3) . . ? C24A C24 N8 71.7(7) . . ? C24A C24 C25 91.8(11) . . ? N8 C24 C25 127.2(7) . . ? C24A C24 C25A 54.3(6) . . ? N8 C24 C25A 107.9(7) . . ? C25 C24 C25A 37.5(7) . . ? C24A C24 C28 105.5(7) . . ? N8 C24 C28 46.7(4) . . ? C25 C24 C28 95.4(8) . . ? C25A C24 C28 104.4(5) . . ? C24 C24A C25A 85.0(7) . . ? C24 C24A N8 59.2(5) . . ? C25A C24A N8 120.0(6) . . ? C24 C24A C25 50.5(7) . . ? C25A C24A C25 34.5(5) . . ? N8 C24A C25 95.2(6) . . ? C25A C25 C26 82.0(10) . . ? C25A C25 C24 86.9(11) . . ? C26 C25 C24 120.8(7) . . ? C25A C25 C24A 49.2(7) . . ? C26 C25 C24A 107.2(8) . . ? C24 C25 C24A 37.7(7) . . ? C25A C25 C27 110.1(8) . . ? C26 C25 C27 47.5(5) . . ? C24 C25 C27 84.3(7) . . ? C24A C25 C27 97.2(5) . . ? C25 C25A C24A 96.3(8) . . ? C25 C25A C26 53.2(7) . . ? C24A C25A C26 118.4(6) . . ? C25 C25A C24 55.6(8) . . ? C24A C25A C24 40.7(5) . . ? C26 C25A C24 90.6(6) . . ? C25 C26 C27 93.5(8) . . ? C25 C26 C25A 44.7(8) . . ? C27 C26 C25A 117.7(4) . . ? C25 C26 N7 123.7(5) . . ? C27 C26 N7 118.1(4) . . ? C25A C26 N7 123.6(4) . . ? C25 C26 C27A 121.4(6) . . ? C27 C26 C27A 59.6(5) . . ? C25A C26 C27A 99.8(5) . . ? N7 C26 C27A 114.8(4) . . ? C26 C27 C28 118.8(6) . . ? C26 C27 C27A 65.4(5) . . ? C28 C27 C27A 88.9(5) . . ? C26 C27 C25 39.0(4) . . ? C28 C27 C25 91.4(5) . . ? C27A C27 C25 90.1(7) . . ? C26 C27 C28A 93.1(5) . . ? C28 C27 C28A 43.3(4) . . ? C27A C27 C28A 45.6(4) . . ? C25 C27 C28A 90.8(5) . . ? C28A C27A C27 85.5(6) . . ? C28A C27A C26 112.9(6) . . ? C27 C27A C26 55.0(4) . . ? C28A C27A C28 41.1(4) . . ? C27 C27A C28 44.3(4) . . ? C26 C27A C28 84.1(4) . . ? N8 C28 C28A 67.4(5) . . ? N8 C28 C27 123.6(5) . . ? C28A C28 C27 90.3(6) . . ? N8 C28 C24 45.5(4) . . ? C28A C28 C24 93.5(6) . . ? C27 C28 C24 88.5(5) . . ? N8 C28 C27A 96.0(4) . . ? C28A C28 C27A 43.5(4) . . ? C27 C28 C27A 46.8(4) . . ? C24 C28 C27A 91.9(5) . . ? C28 C28A C27A 95.4(6) . . ? C28 C28A N8 55.3(4) . . ? C27A C28A N8 123.2(6) . . ? C28 C28A C27 46.5(4) . . ? C27A C28A C27 48.9(5) . . ? N8 C28A C27 87.9(4) . . ? C9 N1 C13 117.5(3) . . ? C9 N1 Zn1 120.8(2) . . ? C13 N1 Zn1 121.7(2) . . ? N3 N2 C11 112.6(3) . . ? N2 N3 C14 113.0(3) . . ? C17 N4 C16 117.9(3) . . ? C17 N4 Zn2 119.5(2) . 1_666 ? C16 N4 Zn2 122.6(2) . 1_666 ? C19 N5 C23 117.4(3) . . ? C19 N5 Zn2 120.0(2) . . ? C23 N5 Zn2 122.5(2) . . ? N6 N6 C21 101.1(5) 2_457 . ? N7 N7 C26 114.1(5) 2_756 . ? C24 N8 C28 87.8(7) . . ? C24 N8 C24A 49.2(6) . . ? C28 N8 C24A 120.3(4) . . ? C24 N8 C28A 113.7(5) . . ? C28 N8 C28A 57.3(4) . . ? C24A N8 C28A 99.5(5) . . ? C24 N8 Zn1 125.7(4) . . ? C28 N8 Zn1 121.8(3) . . ? C24A N8 Zn1 117.2(3) . . ? C28A N8 Zn1 120.6(3) . . ? C1 O1 Zn1 111.7(2) . . ? C5 O5 Zn2 99.7(2) . . ? C5 O6 Zn2 80.9(3) . . ? C8 O7 Zn1 80.77(19) . . ? C8 O8 Zn1 100.29(19) . . ? O1 Zn1 O8 112.95(11) . . ? O1 Zn1 N8 124.89(11) . . ? O8 Zn1 N8 110.60(10) . . ? O1 Zn1 N1 102.87(11) . . ? O8 Zn1 N1 95.86(9) . . ? N8 Zn1 N1 104.57(10) . . ? O1 Zn1 O7 89.11(11) . . ? O8 Zn1 O7 57.50(9) . . ? N8 Zn1 O7 87.02(10) . . ? N1 Zn1 O7 153.36(9) . . ? O1 Zn1 C8 101.72(11) . . ? O8 Zn1 C8 29.09(10) . . ? N8 Zn1 C8 100.16(10) . . ? N1 Zn1 C8 124.94(10) . . ? O7 Zn1 C8 28.41(9) . . ? O3 Zn2 O5 104.32(12) . . ? O3 Zn2 N5 137.74(12) . . ? O5 Zn2 N5 108.05(11) . . ? O3 Zn2 N4 101.99(11) . 1_444 ? O5 Zn2 N4 99.78(12) . 1_444 ? N5 Zn2 N4 98.55(9) . 1_444 ? O3 Zn2 O4 56.11(11) . . ? O5 Zn2 O4 158.96(13) . . ? N5 Zn2 O4 86.62(10) . . ? N4 Zn2 O4 92.60(14) 1_444 . ? O3 Zn2 O6 89.00(11) . . ? O5 Zn2 O6 56.68(12) . . ? N5 Zn2 O6 86.71(10) . . ? N4 Zn2 O6 156.14(11) 1_444 . ? O4 Zn2 O6 111.00(14) . . ? O3 Zn2 C4 28.13(13) . . ? O5 Zn2 C4 131.96(13) . . ? N5 Zn2 C4 112.44(11) . . ? N4 Zn2 C4 98.71(11) 1_444 . ? O4 Zn2 C4 27.99(11) . . ? O6 Zn2 C4 100.73(12) . . ? O3 Zn2 C5 97.37(11) . . ? O5 Zn2 C5 28.90(14) . . ? N5 Zn2 C5 98.00(11) . . ? N4 Zn2 C5 128.59(14) 1_444 . ? O4 Zn2 C5 136.71(16) . . ? O6 Zn2 C5 27.78(13) . . ? C4 Zn2 C5 118.74(12) . . ? C2 C3 C4 123.2(4) . . ? C3 C2 C1 123.2(4) . . ? O4 C4 O3 120.8(3) . . ? O4 C4 C3 121.5(4) . . ? O3 C4 C3 117.6(4) . . ? O4 C4 Zn2 70.7(2) . . ? O3 C4 Zn2 50.17(19) . . ? C3 C4 Zn2 167.5(3) . . ? C4 O3 Zn2 101.7(3) . . ? C4 O4 Zn2 81.3(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.998 _refine_diff_density_min -0.953 _refine_diff_density_rms 0.091 _database_code_depnum_ccdc_archive 'CCDC 974223'