# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm #TrackingRef '- crystals.cif' _journal_coden_Cambridge 1350 _publ_contact_author_name 'Jian-Fang Ma' _publ_contact_author_address ; Department of Chemistry Northeast Normal University Changchun 130024 P.R.China ; _publ_contact_author_email jianfangma@yahoo.com.cn _publ_contact_author_phone +86-431-85098620 _publ_contact_author_fax +86-431-85098620 _publ_author_name 'Jian-Fang Ma.' #============================================================================== data_1 _database_code_depnum_ccdc_archive 'CCDC 806433' #TrackingRef '- crystals.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 N4 O4 Zn' _chemical_formula_weight 626.01 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 Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.5556(7) _cell_length_b 8.7941(2) _cell_length_c 16.2863(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.318(3) _cell_angle_gamma 90.00 _cell_volume 3178.25(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3653 _cell_measurement_theta_min 4.69 _cell_measurement_theta_max 29.22 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 0.815 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_T_max 0.80 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6940 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0502 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.69 _diffrn_reflns_theta_max 29.22 _reflns_number_total 3653 _reflns_number_gt 2802 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.1375P)^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 SHELXL _refine_ls_extinction_coef 0.022(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3653 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0762 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1875 _refine_ls_wR_factor_gt 0.1769 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5669(3) -0.1255(8) 0.1637(4) 0.0932(17) Uani 1 1 d . . . H1A H 0.5720 -0.0899 0.2203 0.140 Uiso 1 1 calc R . . H1B H 0.5955 -0.0759 0.1357 0.140 Uiso 1 1 calc R . . H1C H 0.5732 -0.2334 0.1636 0.140 Uiso 1 1 calc R . . C2 C 0.5058(2) -0.0909(5) 0.1207(3) 0.0645(11) Uani 1 1 d . . . C3 C 0.4209(2) -0.1038(5) 0.0294(3) 0.0665(11) Uani 1 1 d . . . C4 C 0.4166(2) 0.0068(5) 0.0897(3) 0.0632(11) Uani 1 1 d . . . C5 C 0.3742(3) -0.1340(8) -0.0358(4) 0.0887(16) Uani 1 1 d . . . H5 H 0.3778 -0.2064 -0.0763 0.106 Uiso 1 1 calc R . . C6 C 0.3627(2) 0.0898(7) 0.0837(4) 0.0816(15) Uani 1 1 d . . . H6 H 0.3582 0.1642 0.1227 0.098 Uiso 1 1 calc R . . C7 C 0.3223(3) -0.0521(9) -0.0381(4) 0.105(2) Uani 1 1 d . . . H7 H 0.2893 -0.0719 -0.0799 0.126 Uiso 1 1 calc R . . C8 C 0.3178(3) 0.0581(8) 0.0199(4) 0.0961(18) Uani 1 1 d . . . H8 H 0.2822 0.1134 0.0149 0.115 Uiso 1 1 calc R . . C9 C 0.5036(3) -0.2807(6) 0.0043(3) 0.0744(13) Uani 1 1 d . . . H9A H 0.5471 -0.2714 0.0148 0.089 Uiso 1 1 calc R . . H9B H 0.4895 -0.2645 -0.0549 0.089 Uiso 1 1 calc R . . C10 C 0.4869(3) -0.4405(5) 0.0266(3) 0.0721(12) Uani 1 1 d . . . H10A H 0.4434 -0.4503 0.0175 0.086 Uiso 1 1 calc R . . H10B H 0.5023 -0.4593 0.0853 0.086 Uiso 1 1 calc R . . C11 C 0.5906(2) 0.3879(5) 0.2570(3) 0.0647(11) Uani 1 1 d . . . C12 C 0.6364(2) 0.5103(5) 0.2526(3) 0.0715(12) Uani 1 1 d . . . C13 C 0.6632(3) 0.5257(7) 0.1838(5) 0.0946(17) Uani 1 1 d . . . H13 H 0.6532 0.4597 0.1388 0.113 Uiso 1 1 calc R . . C14 C 0.7045(4) 0.6389(10) 0.1816(7) 0.117(2) Uani 1 1 d . . . H14 H 0.7238 0.6449 0.1358 0.140 Uiso 1 1 calc R . . C15 C 0.7180(3) 0.7384(12) 0.2412(11) 0.147(4) Uani 1 1 d . . . H15 H 0.7443 0.8178 0.2362 0.177 Uiso 1 1 calc R . . C16 C 0.6921(4) 0.7242(9) 0.3133(8) 0.124(3) Uani 1 1 d . . . H16 H 0.7027 0.7916 0.3575 0.149 Uiso 1 1 calc R . . C17 C 0.6515(3) 0.6120(7) 0.3184(4) 0.0915(17) Uani 1 1 d . . . H17 H 0.6339 0.6032 0.3656 0.110 Uiso 1 1 calc R . . N1 N 0.4786(2) -0.1631(4) 0.0507(3) 0.0658(10) Uani 1 1 d . . . N2 N 0.46981(18) 0.0134(4) 0.1458(2) 0.0647(9) Uani 1 1 d . . . O1 O 0.5810(2) 0.2914(4) 0.1994(3) 0.0841(11) Uani 1 1 d . . . O2 O 0.5637(2) 0.3858(5) 0.3171(2) 0.0886(11) Uani 1 1 d . . . Zn1 Zn 0.5000 0.18560(5) 0.2500 0.0334(3) Uani 1 2 d S . . 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 0.099(4) 0.087(4) 0.092(4) 0.000(3) 0.010(3) 0.036(3) C2 0.087(3) 0.044(2) 0.063(2) -0.0001(18) 0.014(2) 0.007(2) C3 0.082(3) 0.060(3) 0.058(2) -0.003(2) 0.013(2) 0.001(2) C4 0.079(3) 0.053(2) 0.058(2) -0.0012(19) 0.013(2) 0.002(2) C5 0.094(4) 0.091(4) 0.077(3) -0.026(3) 0.006(3) 0.001(3) C6 0.078(3) 0.083(3) 0.081(3) -0.012(3) 0.007(3) 0.016(3) C7 0.093(4) 0.121(5) 0.090(4) -0.017(4) -0.011(3) 0.003(4) C8 0.081(3) 0.108(5) 0.095(4) -0.013(4) 0.004(3) 0.016(3) C9 0.108(4) 0.059(2) 0.065(3) -0.003(2) 0.039(3) 0.006(3) C10 0.101(3) 0.055(2) 0.066(3) -0.008(2) 0.032(2) 0.008(2) C11 0.084(3) 0.054(2) 0.057(2) 0.000(2) 0.014(2) -0.001(2) C12 0.073(3) 0.052(2) 0.085(3) 0.003(2) 0.003(2) 0.008(2) C13 0.097(4) 0.076(4) 0.120(5) 0.000(3) 0.044(4) 0.003(3) C14 0.105(5) 0.101(5) 0.155(7) -0.001(5) 0.049(5) -0.020(4) C15 0.077(4) 0.104(6) 0.260(14) 0.014(8) 0.028(6) -0.025(4) C16 0.094(5) 0.084(4) 0.172(9) -0.008(5) -0.035(5) -0.017(4) C17 0.098(4) 0.071(3) 0.096(4) -0.007(3) -0.010(3) -0.005(3) N1 0.086(3) 0.052(2) 0.060(2) -0.0030(16) 0.0152(19) 0.0034(18) N2 0.077(2) 0.0535(19) 0.061(2) -0.0068(16) 0.0074(17) 0.0074(17) O1 0.100(3) 0.072(2) 0.083(2) -0.0164(18) 0.023(2) -0.0117(18) O2 0.116(3) 0.085(2) 0.070(2) -0.0094(19) 0.030(2) -0.019(2) Zn1 0.0502(4) 0.0231(3) 0.0262(3) 0.000 0.0049(2) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.461(8) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N2 1.337(6) . ? C2 N1 1.352(6) . ? C3 C5 1.382(7) . ? C3 N1 1.386(7) . ? C3 C4 1.398(6) . ? C4 N2 1.374(6) . ? C4 C6 1.407(7) . ? C5 C7 1.369(9) . ? C5 H5 0.9300 . ? C6 C8 1.344(8) . ? C6 H6 0.9300 . ? C7 C8 1.370(9) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 N1 1.453(6) . ? C9 C10 1.515(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C10 1.542(9) 5_645 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O2 1.240(6) . ? C11 O1 1.255(6) . ? C11 C12 1.503(7) . ? C12 C13 1.371(8) . ? C12 C17 1.390(8) . ? C13 C14 1.369(10) . ? C13 H13 0.9300 . ? C14 C15 1.301(16) . ? C14 H14 0.9300 . ? C15 C16 1.408(17) . ? C15 H15 0.9300 . ? C16 C17 1.358(11) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? N2 Zn1 2.285(4) . ? O1 Zn1 2.328(4) . ? O2 Zn1 2.408(4) . ? Zn1 N2 2.285(4) 2_655 ? Zn1 O1 2.328(4) 2_655 ? Zn1 O2 2.408(4) 2_655 ? 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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N2 C2 N1 111.8(4) . . ? N2 C2 C1 124.6(4) . . ? N1 C2 C1 123.6(4) . . ? C5 C3 N1 132.3(5) . . ? C5 C3 C4 122.2(5) . . ? N1 C3 C4 105.5(4) . . ? N2 C4 C3 109.5(4) . . ? N2 C4 C6 131.8(4) . . ? C3 C4 C6 118.8(4) . . ? C7 C5 C3 116.8(5) . . ? C7 C5 H5 121.6 . . ? C3 C5 H5 121.6 . . ? C8 C6 C4 117.9(5) . . ? C8 C6 H6 121.0 . . ? C4 C6 H6 121.0 . . ? C5 C7 C8 121.5(6) . . ? C5 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C6 C8 C7 122.8(6) . . ? C6 C8 H8 118.6 . . ? C7 C8 H8 118.6 . . ? N1 C9 C10 113.5(4) . . ? N1 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? N1 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C9 C10 C10 111.0(5) . 5_645 ? C9 C10 H10A 109.4 . . ? C10 C10 H10A 109.4 5_645 . ? C9 C10 H10B 109.4 . . ? C10 C10 H10B 109.4 5_645 . ? H10A C10 H10B 108.0 . . ? O2 C11 O1 122.4(5) . . ? O2 C11 C12 119.1(4) . . ? O1 C11 C12 118.5(4) . . ? C13 C12 C17 118.9(6) . . ? C13 C12 C11 121.1(5) . . ? C17 C12 C11 120.0(5) . . ? C14 C13 C12 119.6(7) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C15 C14 C13 122.6(9) . . ? C15 C14 H14 118.7 . . ? C13 C14 H14 118.7 . . ? C14 C15 C16 119.1(8) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? C17 C16 C15 120.0(9) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C12 119.7(8) . . ? C16 C17 H17 120.1 . . ? C12 C17 H17 120.1 . . ? C2 N1 C3 107.4(4) . . ? C2 N1 C9 127.8(5) . . ? C3 N1 C9 124.9(4) . . ? C2 N2 C4 105.9(4) . . ? C2 N2 Zn1 124.4(3) . . ? C4 N2 Zn1 129.1(3) . . ? C11 O1 Zn1 92.7(3) . . ? C11 O2 Zn1 89.4(3) . . ? N2 Zn1 N2 97.00(19) . 2_655 ? N2 Zn1 O1 98.65(14) . . ? N2 Zn1 O1 112.31(15) 2_655 . ? N2 Zn1 O1 112.31(15) . 2_655 ? N2 Zn1 O1 98.65(14) 2_655 2_655 ? O1 Zn1 O1 132.86(19) . 2_655 ? N2 Zn1 O2 153.60(15) . . ? N2 Zn1 O2 94.21(14) 2_655 . ? O1 Zn1 O2 54.96(13) . . ? O1 Zn1 O2 89.39(15) 2_655 . ? N2 Zn1 O2 94.21(14) . 2_655 ? N2 Zn1 O2 153.60(15) 2_655 2_655 ? O1 Zn1 O2 89.39(15) . 2_655 ? O1 Zn1 O2 54.96(13) 2_655 2_655 ? O2 Zn1 O2 86.0(2) . 2_655 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C3 C4 N2 -179.1(5) . . . . ? N1 C3 C4 N2 -0.2(5) . . . . ? C5 C3 C4 C6 0.1(8) . . . . ? N1 C3 C4 C6 179.0(5) . . . . ? N1 C3 C5 C7 -179.8(6) . . . . ? C4 C3 C5 C7 -1.3(9) . . . . ? N2 C4 C6 C8 179.1(6) . . . . ? C3 C4 C6 C8 0.1(8) . . . . ? C3 C5 C7 C8 2.3(11) . . . . ? C4 C6 C8 C7 1.0(10) . . . . ? C5 C7 C8 C6 -2.2(12) . . . . ? N1 C9 C10 C10 178.2(6) . . . 5_645 ? O2 C11 C12 C13 -173.9(5) . . . . ? O1 C11 C12 C13 6.0(7) . . . . ? O2 C11 C12 C17 4.9(7) . . . . ? O1 C11 C12 C17 -175.2(5) . . . . ? C17 C12 C13 C14 0.9(9) . . . . ? C11 C12 C13 C14 179.7(6) . . . . ? C12 C13 C14 C15 -3.2(13) . . . . ? C13 C14 C15 C16 4.2(15) . . . . ? C14 C15 C16 C17 -3.0(14) . . . . ? C15 C16 C17 C12 0.9(11) . . . . ? C13 C12 C17 C16 0.1(9) . . . . ? C11 C12 C17 C16 -178.7(6) . . . . ? N2 C2 N1 C3 -0.8(5) . . . . ? C1 C2 N1 C3 178.2(5) . . . . ? N2 C2 N1 C9 178.8(4) . . . . ? C1 C2 N1 C9 -2.2(8) . . . . ? C5 C3 N1 C2 179.3(6) . . . . ? C4 C3 N1 C2 0.6(5) . . . . ? C5 C3 N1 C9 -0.3(9) . . . . ? C4 C3 N1 C9 -179.0(4) . . . . ? C10 C9 N1 C2 96.7(7) . . . . ? C10 C9 N1 C3 -83.8(6) . . . . ? N1 C2 N2 C4 0.6(5) . . . . ? C1 C2 N2 C4 -178.4(5) . . . . ? N1 C2 N2 Zn1 -171.4(3) . . . . ? C1 C2 N2 Zn1 9.7(7) . . . . ? C3 C4 N2 C2 -0.2(5) . . . . ? C6 C4 N2 C2 -179.3(5) . . . . ? C3 C4 N2 Zn1 171.2(3) . . . . ? C6 C4 N2 Zn1 -7.9(8) . . . . ? O2 C11 O1 Zn1 7.4(5) . . . . ? C12 C11 O1 Zn1 -172.5(4) . . . . ? O1 C11 O2 Zn1 -7.1(5) . . . . ? C12 C11 O2 Zn1 172.8(4) . . . . ? C2 N2 Zn1 N2 -59.7(3) . . . 2_655 ? C4 N2 Zn1 N2 130.2(5) . . . 2_655 ? C2 N2 Zn1 O1 54.2(4) . . . . ? C4 N2 Zn1 O1 -115.8(4) . . . . ? C2 N2 Zn1 O1 -162.1(4) . . . 2_655 ? C4 N2 Zn1 O1 27.9(4) . . . 2_655 ? C2 N2 Zn1 O2 54.7(5) . . . . ? C4 N2 Zn1 O2 -115.3(5) . . . . ? C2 N2 Zn1 O2 144.2(4) . . . 2_655 ? C4 N2 Zn1 O2 -25.8(4) . . . 2_655 ? C11 O1 Zn1 N2 175.8(3) . . . . ? C11 O1 Zn1 N2 -82.9(3) . . . 2_655 ? C11 O1 Zn1 O1 44.1(3) . . . 2_655 ? C11 O1 Zn1 O2 -3.9(3) . . . . ? C11 O1 Zn1 O2 81.6(3) . . . 2_655 ? C11 O2 Zn1 N2 3.3(5) . . . . ? C11 O2 Zn1 N2 118.3(3) . . . 2_655 ? C11 O2 Zn1 O1 3.9(3) . . . . ? C11 O2 Zn1 O1 -143.0(3) . . . 2_655 ? C11 O2 Zn1 O2 -88.1(3) . . . 2_655 ? _diffrn_measured_fraction_theta_max 0.845 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.867 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.099 #==== data_2 _database_code_depnum_ccdc_archive 'CCDC 806434' #TrackingRef '- crystals.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 N4 O6 Zn' _chemical_formula_weight 658.01 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 Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.4668(10) _cell_length_b 8.6151(3) _cell_length_c 16.9974(6) _cell_angle_alpha 90.00 _cell_angle_beta 102.055(4) _cell_angle_gamma 90.00 _cell_volume 3217.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3718 _cell_measurement_theta_min 4.63 _cell_measurement_theta_max 29.23 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 0.814 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.752 _exptl_absorpt_correction_T_max 0.793 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7914 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0988 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.63 _diffrn_reflns_theta_max 29.23 _reflns_number_total 3718 _reflns_number_gt 2194 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.1075P)^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 SHELXL _refine_ls_extinction_coef 0.0129(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3718 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1081 _refine_ls_R_factor_gt 0.0633 _refine_ls_wR_factor_ref 0.1798 _refine_ls_wR_factor_gt 0.1629 _refine_ls_goodness_of_fit_ref 0.952 _refine_ls_restrained_S_all 0.952 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0665(3) -0.1306(9) 0.6697(5) 0.104(2) Uani 1 1 d . . . H1A H 1.0836 -0.0418 0.7003 0.156 Uiso 1 1 calc R . . H1B H 1.0921 -0.1600 0.6334 0.156 Uiso 1 1 calc R . . H1C H 1.0637 -0.2152 0.7054 0.156 Uiso 1 1 calc R . . C2 C 1.0053(3) -0.0919(6) 0.6234(3) 0.0713(14) Uani 1 1 d . . . C3 C 0.9138(3) 0.0080(6) 0.5894(3) 0.0735(14) Uani 1 1 d . . . C4 C 0.8611(3) 0.0876(8) 0.5854(4) 0.0960(19) Uani 1 1 d . . . H4 H 0.8553 0.1541 0.6263 0.115 Uiso 1 1 calc R . . C5 C 0.8168(4) 0.0642(11) 0.5176(5) 0.120(3) Uani 1 1 d . . . H5 H 0.7814 0.1230 0.5110 0.144 Uiso 1 1 calc R . . C6 C 0.8219(4) -0.0406(11) 0.4592(5) 0.128(3) Uani 1 1 d . . . H6 H 0.7893 -0.0565 0.4163 0.153 Uiso 1 1 calc R . . C7 C 0.8761(4) -0.1247(10) 0.4634(4) 0.109(2) Uani 1 1 d . . . H7 H 0.8811 -0.1949 0.4237 0.130 Uiso 1 1 calc R . . C8 C 0.9204(3) -0.0967(7) 0.5291(3) 0.0750(15) Uani 1 1 d . . . C9 C 1.0048(3) -0.2776(7) 0.5073(4) 0.0863(18) Uani 1 1 d . . . H9A H 1.0488 -0.2689 0.5202 0.104 Uiso 1 1 calc R . . H9B H 0.9913 -0.2569 0.4502 0.104 Uiso 1 1 calc R . . C10 C 0.9874(3) -0.4424(7) 0.5240(3) 0.0809(16) Uani 1 1 d . . . H10A H 1.0019 -0.4648 0.5807 0.097 Uiso 1 1 calc R . . H10B H 0.9434 -0.4512 0.5122 0.097 Uiso 1 1 calc R . . C11 C 1.0914(3) 0.3861(7) 0.7473(4) 0.0726(14) Uani 1 1 d . . . C12 C 1.1384(3) 0.5072(7) 0.7445(4) 0.0845(17) Uani 1 1 d . . . C13 C 1.1638(4) 0.5179(10) 0.6774(5) 0.117(3) Uani 1 1 d . . . H13 H 1.1525 0.4474 0.6355 0.140 Uiso 1 1 calc R . . C14 C 1.2048(4) 0.6296(15) 0.6719(9) 0.157(4) Uani 1 1 d . . . H14 H 1.2209 0.6379 0.6259 0.189 Uiso 1 1 calc R . . C15 C 1.2229(4) 0.7328(14) 0.7360(10) 0.148(4) Uani 1 1 d . . . H15 H 1.2516 0.8094 0.7332 0.178 Uiso 1 1 calc R . . C16 C 1.1997(4) 0.7211(11) 0.7987(7) 0.129(3) Uani 1 1 d . . . H16 H 1.2124 0.7906 0.8407 0.154 Uiso 1 1 calc R . . C17 C 1.1574(3) 0.6121(9) 0.8068(5) 0.099(2) Uani 1 1 d . . . N1 N 0.9690(2) 0.0103(5) 0.6481(3) 0.0742(12) Uani 1 1 d . . . N2 N 0.9790(3) -0.1585(5) 0.5527(3) 0.0803(13) Uani 1 1 d . . . O1 O 1.0771(2) 0.2909(5) 0.6954(3) 0.0992(13) Uani 1 1 d . . . O2 O 1.0674(2) 0.3874(6) 0.8112(3) 0.1021(14) Uani 1 1 d . . . O3 O 1.1359(4) 0.6097(9) 0.8731(4) 0.155(2) Uani 1 1 d . . . H3 H 1.1111 0.5392 0.8705 0.186 Uiso 1 1 calc R . . Zn1 Zn 1.0000 0.17872(6) 0.7500 0.0361(3) Uani 1 2 d S . . 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 0.102(5) 0.104(5) 0.102(5) -0.003(4) 0.014(4) 0.037(4) C2 0.088(4) 0.052(3) 0.074(3) -0.004(3) 0.019(3) 0.011(3) C3 0.087(4) 0.060(3) 0.071(3) -0.004(3) 0.011(3) 0.005(3) C4 0.078(4) 0.091(5) 0.112(5) -0.021(4) 0.004(4) 0.013(3) C5 0.093(5) 0.123(6) 0.130(6) -0.027(6) -0.012(5) 0.026(5) C6 0.117(6) 0.138(7) 0.113(6) -0.030(6) -0.009(5) 0.018(6) C7 0.131(6) 0.102(5) 0.084(4) -0.023(4) 0.001(4) 0.011(5) C8 0.094(4) 0.061(3) 0.065(3) -0.002(3) 0.007(3) 0.009(3) C9 0.128(5) 0.062(4) 0.078(3) -0.004(3) 0.044(4) 0.009(3) C10 0.111(4) 0.063(3) 0.075(3) -0.005(3) 0.034(3) 0.008(3) C11 0.076(4) 0.056(3) 0.085(4) 0.006(3) 0.017(3) -0.003(3) C12 0.080(4) 0.065(4) 0.105(4) 0.014(3) 0.013(3) 0.006(3) C13 0.108(5) 0.116(6) 0.139(6) 0.023(5) 0.056(5) 0.004(5) C14 0.101(7) 0.153(9) 0.227(13) 0.036(9) 0.058(8) -0.013(6) C15 0.100(7) 0.121(8) 0.222(13) 0.013(9) 0.031(8) -0.031(6) C16 0.104(6) 0.107(6) 0.163(9) 0.016(6) -0.001(6) -0.028(5) C17 0.097(5) 0.083(4) 0.106(5) -0.008(4) -0.001(4) -0.006(4) N1 0.089(3) 0.059(3) 0.071(3) -0.006(2) 0.008(2) 0.010(2) N2 0.111(4) 0.053(3) 0.076(3) -0.003(2) 0.016(3) 0.010(3) O1 0.116(4) 0.087(3) 0.099(3) -0.016(3) 0.033(3) -0.007(3) O2 0.133(4) 0.093(3) 0.087(3) 0.004(2) 0.038(3) -0.018(3) O3 0.196(7) 0.155(6) 0.111(4) -0.036(4) 0.027(4) -0.043(5) Zn1 0.0534(4) 0.0248(3) 0.0297(3) 0.000 0.0076(2) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.472(8) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N1 1.327(6) . ? C2 N2 1.352(7) . ? C3 C4 1.357(8) . ? C3 C8 1.397(7) . ? C3 N1 1.420(7) . ? C4 C5 1.371(9) . ? C4 H4 0.9300 . ? C5 C6 1.364(11) . ? C5 H5 0.9300 . ? C6 C7 1.405(11) . ? C6 H6 0.9300 . ? C7 C8 1.353(9) . ? C7 H7 0.9300 . ? C8 N2 1.400(8) . ? C9 N2 1.473(7) . ? C9 C10 1.515(8) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C10 1.472(10) 5_746 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O1 1.198(7) . ? C11 O2 1.310(7) . ? C11 C12 1.493(8) . ? C12 C13 1.380(9) . ? C12 C17 1.389(10) . ? C13 C14 1.349(12) . ? C13 H13 0.9300 . ? C14 C15 1.399(17) . ? C14 H14 0.9300 . ? C15 C16 1.285(13) . ? C15 H15 0.9300 . ? C16 C17 1.364(12) . ? C16 H16 0.9300 . ? C17 O3 1.315(9) . ? N1 Zn1 2.256(4) . ? O1 Zn1 2.338(5) . ? O2 Zn1 2.440(5) . ? O3 H3 0.8200 . ? Zn1 N1 2.256(4) 2_756 ? Zn1 O1 2.338(5) 2_756 ? Zn1 O2 2.440(5) 2_756 ? 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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 N2 112.3(5) . . ? N1 C2 C1 123.3(5) . . ? N2 C2 C1 124.4(5) . . ? C4 C3 C8 121.0(6) . . ? C4 C3 N1 130.8(5) . . ? C8 C3 N1 108.2(5) . . ? C3 C4 C5 116.1(7) . . ? C3 C4 H4 122.0 . . ? C5 C4 H4 122.0 . . ? C6 C5 C4 123.5(7) . . ? C6 C5 H5 118.2 . . ? C4 C5 H5 118.2 . . ? C5 C6 C7 120.5(7) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 115.4(7) . . ? C8 C7 H7 122.3 . . ? C6 C7 H7 122.3 . . ? C7 C8 C3 123.2(6) . . ? C7 C8 N2 130.9(6) . . ? C3 C8 N2 105.9(5) . . ? N2 C9 C10 114.2(5) . . ? N2 C9 H9A 108.7 . . ? C10 C9 H9A 108.7 . . ? N2 C9 H9B 108.7 . . ? C10 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C10 C10 C9 112.6(6) 5_746 . ? C10 C10 H10A 109.1 5_746 . ? C9 C10 H10A 109.1 . . ? C10 C10 H10B 109.1 5_746 . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? O1 C11 O2 121.5(5) . . ? O1 C11 C12 122.6(6) . . ? O2 C11 C12 115.9(6) . . ? C13 C12 C17 118.2(7) . . ? C13 C12 C11 119.3(7) . . ? C17 C12 C11 122.4(6) . . ? C14 C13 C12 120.7(10) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 119.4(11) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 119.6(10) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 123.4(10) . . ? C15 C16 H16 118.3 . . ? C17 C16 H16 118.3 . . ? O3 C17 C16 119.0(8) . . ? O3 C17 C12 122.3(7) . . ? C16 C17 C12 118.7(8) . . ? C2 N1 C3 105.9(4) . . ? C2 N1 Zn1 123.9(4) . . ? C3 N1 Zn1 129.2(3) . . ? C2 N2 C8 107.7(4) . . ? C2 N2 C9 127.9(6) . . ? C8 N2 C9 124.3(5) . . ? C11 O1 Zn1 95.6(4) . . ? C11 O2 Zn1 88.1(3) . . ? C17 O3 H3 109.5 . . ? N1 Zn1 N1 99.9(2) . 2_756 ? N1 Zn1 O1 115.82(17) . 2_756 ? N1 Zn1 O1 95.53(17) 2_756 2_756 ? N1 Zn1 O1 95.53(17) . . ? N1 Zn1 O1 115.82(17) 2_756 . ? O1 Zn1 O1 131.2(2) 2_756 . ? N1 Zn1 O2 94.69(16) . 2_756 ? N1 Zn1 O2 150.03(16) 2_756 2_756 ? O1 Zn1 O2 54.49(15) 2_756 2_756 ? O1 Zn1 O2 88.36(17) . 2_756 ? N1 Zn1 O2 150.03(17) . . ? N1 Zn1 O2 94.69(16) 2_756 . ? O1 Zn1 O2 88.36(17) 2_756 . ? O1 Zn1 O2 54.49(16) . . ? O2 Zn1 O2 85.1(3) 2_756 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 C3 C4 C5 -3.0(10) . . . . ? N1 C3 C4 C5 176.7(7) . . . . ? C3 C4 C5 C6 4.9(13) . . . . ? C4 C5 C6 C7 -4.4(15) . . . . ? C5 C6 C7 C8 1.7(13) . . . . ? C6 C7 C8 C3 0.1(11) . . . . ? C6 C7 C8 N2 179.9(7) . . . . ? C4 C3 C8 C7 0.6(10) . . . . ? N1 C3 C8 C7 -179.1(6) . . . . ? C4 C3 C8 N2 -179.2(6) . . . . ? N1 C3 C8 N2 1.1(6) . . . . ? N2 C9 C10 C10 178.5(7) . . . 5_746 ? O1 C11 C12 C13 4.5(9) . . . . ? O2 C11 C12 C13 -177.0(6) . . . . ? O1 C11 C12 C17 -176.4(6) . . . . ? O2 C11 C12 C17 2.1(9) . . . . ? C17 C12 C13 C14 -1.5(11) . . . . ? C11 C12 C13 C14 177.7(7) . . . . ? C12 C13 C14 C15 1.7(15) . . . . ? C13 C14 C15 C16 -0.9(18) . . . . ? C14 C15 C16 C17 -0.2(18) . . . . ? C15 C16 C17 O3 -179.6(10) . . . . ? C15 C16 C17 C12 0.4(15) . . . . ? C13 C12 C17 O3 -179.6(7) . . . . ? C11 C12 C17 O3 1.3(11) . . . . ? C13 C12 C17 C16 0.4(11) . . . . ? C11 C12 C17 C16 -178.7(7) . . . . ? N2 C2 N1 C3 1.3(6) . . . . ? C1 C2 N1 C3 -176.9(6) . . . . ? N2 C2 N1 Zn1 -168.4(3) . . . . ? C1 C2 N1 Zn1 13.4(8) . . . . ? C4 C3 N1 C2 178.9(6) . . . . ? C8 C3 N1 C2 -1.5(6) . . . . ? C4 C3 N1 Zn1 -12.2(9) . . . . ? C8 C3 N1 Zn1 167.5(4) . . . . ? N1 C2 N2 C8 -0.7(6) . . . . ? C1 C2 N2 C8 177.5(6) . . . . ? N1 C2 N2 C9 -179.2(5) . . . . ? C1 C2 N2 C9 -1.0(9) . . . . ? C7 C8 N2 C2 179.9(7) . . . . ? C3 C8 N2 C2 -0.3(6) . . . . ? C7 C8 N2 C9 -1.5(10) . . . . ? C3 C8 N2 C9 178.3(5) . . . . ? C10 C9 N2 C2 94.9(8) . . . . ? C10 C9 N2 C8 -83.5(7) . . . . ? O2 C11 O1 Zn1 5.6(6) . . . . ? C12 C11 O1 Zn1 -175.9(5) . . . . ? O1 C11 O2 Zn1 -5.4(6) . . . . ? C12 C11 O2 Zn1 176.1(4) . . . . ? C2 N1 Zn1 N1 -61.4(4) . . . 2_756 ? C3 N1 Zn1 N1 131.5(5) . . . 2_756 ? C2 N1 Zn1 O1 -162.5(4) . . . 2_756 ? C3 N1 Zn1 O1 30.3(5) . . . 2_756 ? C2 N1 Zn1 O1 56.1(4) . . . . ? C3 N1 Zn1 O1 -111.1(5) . . . . ? C2 N1 Zn1 O2 144.9(4) . . . 2_756 ? C3 N1 Zn1 O2 -22.3(5) . . . 2_756 ? C2 N1 Zn1 O2 56.6(6) . . . . ? C3 N1 Zn1 O2 -110.5(5) . . . . ? C11 O1 Zn1 N1 176.5(4) . . . . ? C11 O1 Zn1 N1 -79.7(4) . . . 2_756 ? C11 O1 Zn1 O1 44.7(4) . . . 2_756 ? C11 O1 Zn1 O2 81.9(4) . . . 2_756 ? C11 O1 Zn1 O2 -3.2(4) . . . . ? C11 O2 Zn1 N1 2.2(5) . . . . ? C11 O2 Zn1 N1 121.5(4) . . . 2_756 ? C11 O2 Zn1 O1 -143.1(4) . . . 2_756 ? C11 O2 Zn1 O1 2.9(3) . . . . ? C11 O2 Zn1 O2 -88.6(3) . . . 2_756 ? 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 O3 H3 O2 0.82 1.81 2.543(8) 148 . _diffrn_measured_fraction_theta_max 0.848 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.627 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.086 #==== data_3 _database_code_depnum_ccdc_archive 'CCDC 806435' #TrackingRef '- crystals.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H30 N6 O8 Zn' _chemical_formula_weight 716.01 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P c c a' _symmetry_space_group_name_Hall '-P 2a 2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' 'x+1/2, -y, -z+1/2' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' '-x-1/2, y, z-1/2' 'x, -y, z-1/2' _cell_length_a 18.6361(5) _cell_length_b 13.5949(9) _cell_length_c 12.7863(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3239.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4384 _cell_measurement_theta_min 4.15 _cell_measurement_theta_max 29.16 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 0.821 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.65 _exptl_absorpt_correction_T_max 0.81 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11837 _diffrn_reflns_av_R_equivalents 0.0734 _diffrn_reflns_av_sigmaI/netI 0.1514 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.15 _diffrn_reflns_theta_max 29.16 _reflns_number_total 3850 _reflns_number_gt 1545 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0301P)^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 3850 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1512 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.0906 _refine_ls_wR_factor_gt 0.0802 _refine_ls_goodness_of_fit_ref 0.853 _refine_ls_restrained_S_all 0.853 _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 1.0000 0.16128(3) 0.2500 0.03994(16) Uani 1 2 d S . . C1 C 0.88930(16) 0.0223(2) 0.2544(3) 0.0475(8) Uani 1 1 d . . . C2 C 0.84446(18) -0.0533(2) 0.1969(2) 0.0419(8) Uani 1 1 d . . . C3 C 0.80466(17) -0.1208(2) 0.2522(3) 0.0536(8) Uani 1 1 d . . . H3 H 0.8033 -0.1170 0.3248 0.064 Uiso 1 1 calc R . . C4 C 0.7672(2) -0.1931(2) 0.2023(3) 0.0561(10) Uani 1 1 d . . . H4 H 0.7409 -0.2392 0.2400 0.067 Uiso 1 1 calc R . . C5 C 0.76926(18) -0.1960(2) 0.0944(3) 0.0472(9) Uani 1 1 d . . . C6 C 0.80660(18) -0.1291(2) 0.0370(3) 0.0536(10) Uani 1 1 d . . . H6 H 0.8064 -0.1318 -0.0357 0.064 Uiso 1 1 calc R . . C7 C 0.84456(19) -0.0574(2) 0.0887(3) 0.0511(9) Uani 1 1 d . . . H7 H 0.8705 -0.0112 0.0507 0.061 Uiso 1 1 calc R . . C8 C 0.9724(2) 0.1536(3) -0.0187(3) 0.0888(15) Uani 1 1 d . . . H8A H 0.9638 0.1046 0.0339 0.133 Uiso 1 1 calc R . . H8B H 0.9980 0.1246 -0.0761 0.133 Uiso 1 1 calc R . . H8C H 0.9274 0.1791 -0.0432 0.133 Uiso 1 1 calc R . . C9 C 1.0156(2) 0.2347(2) 0.0265(3) 0.0566(11) Uani 1 1 d . . . C10 C 1.07211(16) 0.3302(2) 0.1348(2) 0.0384(7) Uani 1 1 d . . . C11 C 1.10407(17) 0.3734(2) 0.2198(2) 0.0468(9) Uani 1 1 d . . . H11 H 1.0970 0.3489 0.2869 0.056 Uiso 1 1 calc R . . C12 C 1.1469(2) 0.4544(2) 0.2026(3) 0.0567(10) Uani 1 1 d . . . H12 H 1.1695 0.4842 0.2592 0.068 Uiso 1 1 calc R . . C13 C 1.1573(2) 0.4925(3) 0.1041(3) 0.0623(10) Uani 1 1 d . . . H13 H 1.1858 0.5481 0.0957 0.075 Uiso 1 1 calc R . . C14 C 1.08381(19) 0.3675(2) 0.0350(3) 0.0510(9) Uani 1 1 d . . . C15 C 1.1265(2) 0.4500(2) 0.0180(3) 0.0671(11) Uani 1 1 d . . . H15 H 1.1337 0.4752 -0.0489 0.081 Uiso 1 1 calc R . . C16 C 1.0516(2) 0.3075(3) -0.1522(3) 0.0772(12) Uani 1 1 d . . . H16A H 1.0980 0.3310 -0.1758 0.093 Uiso 1 1 calc R . . H16B H 1.0431 0.2427 -0.1816 0.093 Uiso 1 1 calc R . . C17 C 0.9957(3) 0.3744(3) -0.1820(3) 0.1093(16) Uani 1 1 d . . . H17A H 1.0036 0.4395 -0.1530 0.131 Uiso 1 1 calc R . . H17B H 0.9489 0.3507 -0.1603 0.131 Uiso 1 1 calc R . . N1 N 0.7291(2) -0.2735(2) 0.0402(3) 0.0738(11) Uani 1 1 d . . . N2 N 1.02812(13) 0.24771(17) 0.12797(19) 0.0418(7) Uani 1 1 d . . . N3 N 1.04842(18) 0.3042(2) -0.0314(2) 0.0674(9) Uani 1 1 d . . . O1 O 0.89422(15) 0.01953(16) 0.34958(18) 0.0771(8) Uani 1 1 d . . . O2 O 0.92130(13) 0.08466(16) 0.19618(16) 0.0590(7) Uani 1 1 d . . . O3 O 0.7103(2) -0.3443(2) 0.0905(2) 0.1257(14) Uani 1 1 d . . . O4 O 0.7217(2) -0.2678(2) -0.0528(3) 0.1117(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0484(3) 0.0422(3) 0.0293(3) 0.000 -0.0028(3) 0.000 C1 0.051(2) 0.0530(18) 0.0386(19) -0.001(2) 0.001(2) -0.0003(15) C2 0.042(2) 0.0475(18) 0.0359(19) -0.0021(16) 0.0017(16) -0.0017(16) C3 0.063(2) 0.0590(19) 0.0384(18) -0.003(2) 0.009(2) -0.0103(16) C4 0.067(3) 0.050(2) 0.052(2) 0.0039(17) 0.015(2) -0.0171(18) C5 0.048(2) 0.0474(18) 0.046(2) -0.0046(17) 0.0028(19) -0.0102(16) C6 0.067(3) 0.054(2) 0.040(2) -0.0010(17) -0.003(2) -0.0138(18) C7 0.057(2) 0.055(2) 0.041(2) 0.0065(18) 0.0023(19) -0.0119(17) C8 0.130(4) 0.097(3) 0.039(2) -0.010(2) -0.005(2) -0.051(3) C9 0.068(3) 0.065(2) 0.037(2) 0.0022(17) -0.003(2) -0.0113(19) C10 0.040(2) 0.0436(17) 0.0312(18) 0.0043(16) -0.0044(15) 0.0007(16) C11 0.056(2) 0.0511(19) 0.033(2) 0.0049(14) -0.0047(17) -0.0066(16) C12 0.060(3) 0.062(2) 0.048(2) -0.0012(18) -0.0040(19) -0.0090(19) C13 0.063(3) 0.056(2) 0.067(3) 0.005(2) -0.001(2) -0.0148(19) C14 0.057(2) 0.062(2) 0.034(2) 0.0055(17) -0.0067(18) -0.0110(18) C15 0.082(3) 0.068(2) 0.051(2) 0.022(2) 0.005(2) -0.018(2) C16 0.087(3) 0.071(2) 0.074(3) -0.005(2) -0.004(3) 0.007(2) C17 0.127(4) 0.109(3) 0.091(3) -0.026(3) -0.017(4) 0.060(3) N1 0.104(3) 0.061(2) 0.057(2) -0.0060(19) 0.008(2) -0.0280(19) N2 0.053(2) 0.0493(14) 0.0236(15) 0.0000(12) -0.0046(12) -0.0031(12) N3 0.096(3) 0.082(2) 0.0240(16) 0.0109(16) -0.0089(17) -0.0278(18) O1 0.116(2) 0.0818(17) 0.0330(15) 0.0016(13) -0.0021(16) -0.0304(15) O2 0.0716(18) 0.0710(14) 0.0343(12) 0.0023(12) -0.0044(12) -0.0318(14) O3 0.200(4) 0.105(2) 0.072(2) -0.0224(19) 0.043(2) -0.091(2) O4 0.180(4) 0.082(2) 0.073(2) 0.0054(19) -0.049(3) -0.049(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 1.926(2) . ? Zn1 O2 1.926(2) 4_755 ? Zn1 N2 2.022(2) . ? Zn1 N2 2.022(2) 4_755 ? C1 O1 1.220(4) . ? C1 O2 1.277(4) . ? C1 C2 1.516(4) . ? C2 C3 1.375(4) . ? C2 C7 1.384(4) . ? C3 C4 1.364(4) . ? C3 H3 0.9300 . ? C4 C5 1.381(4) . ? C4 H4 0.9300 . ? C5 C6 1.361(4) . ? C5 N1 1.465(4) . ? C6 C7 1.374(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.483(4) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N2 1.329(4) . ? C9 N3 1.347(4) . ? C10 C11 1.371(4) . ? C10 N2 1.392(4) . ? C10 C14 1.390(4) . ? C11 C12 1.379(4) . ? C11 H11 0.9300 . ? C12 C13 1.375(4) . ? C12 H12 0.9300 . ? C13 C15 1.369(5) . ? C13 H13 0.9300 . ? C14 N3 1.378(4) . ? C14 C15 1.392(4) . ? C15 H15 0.9300 . ? C16 C17 1.434(5) . ? C16 N3 1.546(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C17 1.747(8) 4_754 ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? N1 O3 1.210(4) . ? N1 O4 1.200(4) . ? 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 O2 114.52(14) . 4_755 ? O2 Zn1 N2 103.65(9) . . ? O2 Zn1 N2 113.11(10) 4_755 . ? O2 Zn1 N2 113.11(10) . 4_755 ? O2 Zn1 N2 103.65(9) 4_755 4_755 ? N2 Zn1 N2 108.96(13) . 4_755 ? O1 C1 O2 124.5(3) . . ? O1 C1 C2 120.3(3) . . ? O2 C1 C2 115.1(3) . . ? C3 C2 C7 119.2(3) . . ? C3 C2 C1 120.0(3) . . ? C7 C2 C1 120.8(3) . . ? C4 C3 C2 121.1(3) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 118.2(3) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? C6 C5 C4 122.3(3) . . ? C6 C5 N1 119.1(3) . . ? C4 C5 N1 118.6(3) . . ? C5 C6 C7 118.6(3) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? C6 C7 C2 120.6(3) . . ? C6 C7 H7 119.7 . . ? C2 C7 H7 119.7 . . ? C9 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C9 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 N3 111.4(3) . . ? N2 C9 C8 125.1(3) . . ? N3 C9 C8 123.6(3) . . ? C11 C10 N2 130.6(3) . . ? C11 C10 C14 120.2(3) . . ? N2 C10 C14 109.2(3) . . ? C10 C11 C12 117.9(3) . . ? C10 C11 H11 121.1 . . ? C12 C11 H11 121.1 . . ? C13 C12 C11 121.9(3) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C15 C13 C12 121.3(3) . . ? C15 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? N3 C14 C10 105.2(3) . . ? N3 C14 C15 132.9(3) . . ? C10 C14 C15 121.8(3) . . ? C13 C15 C14 117.0(3) . . ? C13 C15 H15 121.5 . . ? C14 C15 H15 121.5 . . ? C17 C16 N3 104.8(3) . . ? C17 C16 H16A 110.8 . . ? N3 C16 H16A 110.8 . . ? C17 C16 H16B 110.8 . . ? N3 C16 H16B 110.8 . . ? H16A C16 H16B 108.9 . . ? C16 C17 C17 101.4(4) . 4_754 ? C16 C17 H17A 111.5 . . ? C17 C17 H17A 111.5 4_754 . ? C16 C17 H17B 111.5 . . ? C17 C17 H17B 111.5 4_754 . ? H17A C17 H17B 109.3 . . ? O3 N1 O4 123.0(3) . . ? O3 N1 C5 118.0(4) . . ? O4 N1 C5 118.8(3) . . ? C9 N2 C10 105.8(3) . . ? C9 N2 Zn1 129.1(2) . . ? C10 N2 Zn1 124.89(19) . . ? C9 N3 C14 108.4(3) . . ? C9 N3 C16 126.0(3) . . ? C14 N3 C16 125.4(3) . . ? C1 O2 Zn1 120.4(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 5.0(5) . . . . ? O2 C1 C2 C3 -176.5(3) . . . . ? O1 C1 C2 C7 -173.1(3) . . . . ? O2 C1 C2 C7 5.3(4) . . . . ? C7 C2 C3 C4 2.0(5) . . . . ? C1 C2 C3 C4 -176.2(3) . . . . ? C2 C3 C4 C5 -1.0(5) . . . . ? C3 C4 C5 C6 -0.6(5) . . . . ? C3 C4 C5 N1 -180.0(3) . . . . ? C4 C5 C6 C7 1.3(5) . . . . ? N1 C5 C6 C7 -179.4(3) . . . . ? C5 C6 C7 C2 -0.2(5) . . . . ? C3 C2 C7 C6 -1.3(5) . . . . ? C1 C2 C7 C6 176.8(3) . . . . ? N2 C10 C11 C12 178.4(3) . . . . ? C14 C10 C11 C12 0.6(5) . . . . ? C10 C11 C12 C13 0.7(5) . . . . ? C11 C12 C13 C15 -1.4(6) . . . . ? C11 C10 C14 N3 176.1(3) . . . . ? N2 C10 C14 N3 -2.1(4) . . . . ? C11 C10 C14 C15 -1.3(5) . . . . ? N2 C10 C14 C15 -179.6(3) . . . . ? C12 C13 C15 C14 0.6(6) . . . . ? N3 C14 C15 C13 -175.9(4) . . . . ? C10 C14 C15 C13 0.7(5) . . . . ? N3 C16 C17 C17 179.3(3) . . . 4_754 ? C6 C5 N1 O3 163.3(4) . . . . ? C4 C5 N1 O3 -17.3(5) . . . . ? C6 C5 N1 O4 -10.6(6) . . . . ? C4 C5 N1 O4 168.8(4) . . . . ? N3 C9 N2 C10 -0.5(4) . . . . ? C8 C9 N2 C10 178.5(3) . . . . ? N3 C9 N2 Zn1 -174.6(2) . . . . ? C8 C9 N2 Zn1 4.4(5) . . . . ? C11 C10 N2 C9 -176.3(3) . . . . ? C14 C10 N2 C9 1.6(4) . . . . ? C11 C10 N2 Zn1 -2.0(5) . . . . ? C14 C10 N2 Zn1 176.0(2) . . . . ? O2 Zn1 N2 C9 -21.4(3) . . . . ? O2 Zn1 N2 C9 103.2(3) 4_755 . . . ? N2 Zn1 N2 C9 -142.1(3) 4_755 . . . ? O2 Zn1 N2 C10 165.5(2) . . . . ? O2 Zn1 N2 C10 -69.9(2) 4_755 . . . ? N2 Zn1 N2 C10 44.8(2) 4_755 . . . ? N2 C9 N3 C14 -0.8(4) . . . . ? C8 C9 N3 C14 -179.8(3) . . . . ? N2 C9 N3 C16 174.2(3) . . . . ? C8 C9 N3 C16 -4.7(6) . . . . ? C10 C14 N3 C9 1.8(4) . . . . ? C15 C14 N3 C9 178.8(4) . . . . ? C10 C14 N3 C16 -173.3(3) . . . . ? C15 C14 N3 C16 3.7(6) . . . . ? C17 C16 N3 C9 98.2(5) . . . . ? C17 C16 N3 C14 -87.5(5) . . . . ? O1 C1 O2 Zn1 15.7(4) . . . . ? C2 C1 O2 Zn1 -162.7(2) . . . . ? O2 Zn1 O2 C1 57.4(2) 4_755 . . . ? N2 Zn1 O2 C1 -178.9(2) . . . . ? N2 Zn1 O2 C1 -61.0(3) 4_755 . . . ? _diffrn_measured_fraction_theta_max 0.878 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.483 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.055 #==== data_4 _database_code_depnum_ccdc_archive 'CCDC 806436' #TrackingRef '- crystals.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H34 N6 O6 Zn' _chemical_formula_weight 664.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8418(3) _cell_length_b 9.5120(4) _cell_length_c 9.6826(4) _cell_angle_alpha 85.966(4) _cell_angle_beta 87.778(3) _cell_angle_gamma 78.915(3) _cell_volume 796.90(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3279 _cell_measurement_theta_min 4.4 _cell_measurement_theta_max 28.2 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 346 _exptl_absorpt_coefficient_mu 0.823 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.71 _exptl_absorpt_correction_T_max 0.80 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5470 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0403 _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 -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.38 _diffrn_reflns_theta_max 28.24 _reflns_number_total 3279 _reflns_number_gt 2852 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. H atoms of water molecule were refined isotropically with distance restraints of O---H = 0.85+-0.02 \%A. The distance of H1A...H1B was restrained to 1.44+-0.02 \%A. ; _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^)+(0.1446P)^2^+0.8147P] 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 SHELXL _refine_ls_extinction_coef 0.37(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3279 _refine_ls_number_parameters 213 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_gt 0.0676 _refine_ls_wR_factor_ref 0.2034 _refine_ls_wR_factor_gt 0.1920 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _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 1.0000 0.0000 1.0000 0.0405(3) Uani 1 2 d S . . C1 C 0.8308(6) 0.1436(7) 1.4224(6) 0.0708(13) Uani 1 1 d . . . C2 C 0.9050(6) 0.1558(6) 1.2987(6) 0.0665(12) Uani 1 1 d . . . C3 C 0.9558(7) 0.2840(6) 1.2525(7) 0.0759(15) Uani 1 1 d . . . H3 H 1.0056 0.2937 1.1670 0.091 Uiso 1 1 calc R . . C4 C 0.9267(9) 0.3950(8) 1.3428(9) 0.095(2) Uani 1 1 d . . . H4 H 0.9599 0.4803 1.3172 0.114 Uiso 1 1 calc R . . C5 C 0.8496(10) 0.3820(10) 1.4701(9) 0.104(2) Uani 1 1 d . . . H5 H 0.8304 0.4591 1.5264 0.125 Uiso 1 1 calc R . . C6 C 0.8008(9) 0.2546(9) 1.5140(8) 0.093(2) Uani 1 1 d . . . H6 H 0.7511 0.2438 1.5994 0.112 Uiso 1 1 calc R . . C7 C 0.8523(7) -0.0560(6) 1.3164(7) 0.0734(14) Uani 1 1 d . . . C8 C 0.8366(10) -0.2019(7) 1.2938(9) 0.099(2) Uani 1 1 d . . . H8A H 0.7294 -0.2082 1.2981 0.148 Uiso 1 1 calc R . . H8B H 0.8904 -0.2666 1.3641 0.148 Uiso 1 1 calc R . . H8C H 0.8797 -0.2271 1.2043 0.148 Uiso 1 1 calc R . . C9 C 0.7155(8) -0.0462(10) 1.5540(7) 0.097(2) Uani 1 1 d . . . H9A H 0.7554 -0.0199 1.6385 0.116 Uiso 1 1 calc R . . H9B H 0.7352 -0.1502 1.5552 0.116 Uiso 1 1 calc R . . C10 C 0.5460(11) 0.008(3) 1.5522(17) 0.349(19) Uani 1 1 d . . . H10A H 0.5036 -0.0337 1.6357 0.418 Uiso 1 1 calc R . . H10B H 0.5310 0.1105 1.5632 0.418 Uiso 1 1 calc R . . C11 C 1.2582(7) -0.2590(6) 1.1119(6) 0.0717(14) Uani 1 1 d . . . C12 C 1.3281(7) -0.4161(6) 1.1349(6) 0.0677(13) Uani 1 1 d . . . C13 C 1.2553(7) -0.5218(6) 1.0883(7) 0.0756(15) Uani 1 1 d . . . H13 H 1.1598 -0.4926 1.0476 0.091 Uiso 1 1 calc R . . C14 C 1.5288(8) -0.6083(8) 1.2098(9) 0.096(2) Uani 1 1 d . . . H14 H 1.6220 -0.6424 1.2531 0.115 Uiso 1 1 calc R . . C15 C 1.4497(9) -0.7010(7) 1.1581(8) 0.0895(19) Uani 1 1 d . . . H15 H 1.4929 -0.7983 1.1649 0.107 Uiso 1 1 calc R . . C16 C 1.4674(8) -0.4579(8) 1.1968(7) 0.0839(17) Uani 1 1 d . . . H16 H 1.5198 -0.3913 1.2291 0.101 Uiso 1 1 calc R . . N1 N 0.7975(6) 0.0092(6) 1.4363(5) 0.0760(12) Uani 1 1 d . . . N2 N 0.9158(5) 0.0296(5) 1.2313(5) 0.0711(12) Uani 1 1 d . . . N3 N 1.3146(7) -0.6609(6) 1.0989(7) 0.0860(15) Uani 1 1 d . . . O1 O 1.1310(5) -0.2288(5) 1.0546(5) 0.0847(12) Uani 1 1 d . . . O2 O 1.3349(7) -0.1726(5) 1.1517(6) 0.1050(16) Uani 1 1 d . . . O1W O 1.2248(6) 0.0824(5) 1.0308(7) 0.1025(16) Uani 1 1 d D . . H1A H 1.266(10) -0.004(5) 1.062(11) 0.154 Uiso 1 1 d D . . H1B H 1.292(9) 0.135(9) 1.004(11) 0.154 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0413(4) 0.0258(4) 0.0544(5) -0.0080(2) 0.0047(2) -0.0060(2) C1 0.060(3) 0.075(3) 0.076(3) -0.003(3) -0.007(2) -0.011(2) C2 0.055(2) 0.061(3) 0.082(3) -0.010(2) -0.006(2) -0.004(2) C3 0.072(3) 0.065(3) 0.093(4) -0.013(3) 0.000(3) -0.016(3) C4 0.099(5) 0.077(4) 0.116(6) -0.017(4) -0.018(4) -0.026(4) C5 0.104(5) 0.107(6) 0.112(6) -0.050(5) -0.005(4) -0.029(4) C6 0.087(4) 0.108(5) 0.086(4) -0.025(4) -0.008(3) -0.013(4) C7 0.064(3) 0.063(3) 0.088(4) 0.002(3) 0.004(3) -0.003(2) C8 0.110(5) 0.061(3) 0.126(6) 0.003(4) 0.018(4) -0.024(3) C9 0.072(4) 0.131(6) 0.082(4) 0.027(4) -0.004(3) -0.016(4) C10 0.069(5) 0.70(5) 0.207(14) 0.28(2) 0.005(7) 0.000(13) C11 0.084(4) 0.060(3) 0.072(3) -0.012(2) 0.003(3) -0.014(3) C12 0.070(3) 0.058(3) 0.073(3) -0.003(2) 0.004(2) -0.009(2) C13 0.070(3) 0.062(3) 0.095(4) -0.001(3) -0.007(3) -0.015(3) C14 0.078(4) 0.084(4) 0.121(6) 0.004(4) -0.025(4) -0.002(3) C15 0.090(4) 0.057(3) 0.115(5) 0.010(3) 0.002(4) -0.005(3) C16 0.087(4) 0.076(4) 0.091(4) -0.009(3) -0.013(3) -0.016(3) N1 0.063(2) 0.079(3) 0.083(3) 0.001(2) -0.006(2) -0.007(2) N2 0.069(3) 0.053(2) 0.090(3) -0.002(2) 0.011(2) -0.013(2) N3 0.084(3) 0.061(3) 0.114(4) 0.000(3) -0.008(3) -0.021(3) O1 0.080(3) 0.065(2) 0.104(3) -0.005(2) -0.007(2) 0.000(2) O2 0.126(4) 0.063(3) 0.129(4) -0.010(3) -0.032(3) -0.018(3) O1W 0.089(3) 0.066(3) 0.158(5) -0.004(3) -0.024(3) -0.026(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 2.297(4) 2_757 ? Zn1 O1 2.297(4) . ? Zn1 O1W 2.309(5) 2_757 ? Zn1 O1W 2.309(5) . ? Zn1 N2 2.351(5) 2_757 ? Zn1 N2 2.351(5) . ? C1 C2 1.352(8) . ? C1 N1 1.362(8) . ? C1 C6 1.406(10) . ? C2 N2 1.392(7) . ? C2 C3 1.417(8) . ? C3 C4 1.398(9) . ? C3 H3 0.9300 . ? C4 C5 1.395(12) . ? C4 H4 0.9300 . ? C5 C6 1.396(12) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N2 1.305(7) . ? C7 N1 1.382(8) . ? C7 C8 1.453(9) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N1 1.449(8) . ? C9 C10 1.489(13) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C10 1.36(4) 2_658 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O2 1.250(8) . ? C11 O1 1.248(8) . ? C11 C12 1.508(8) . ? C12 C16 1.368(9) . ? C12 C13 1.401(8) . ? C13 N3 1.325(8) . ? C13 H13 0.9300 . ? C14 C15 1.358(11) . ? C14 C16 1.428(10) . ? C14 H14 0.9300 . ? C15 N3 1.322(9) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? O1W H1A 0.87(2) . ? O1W H1B 0.86(2) . ? 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 O1 180 2_757 . ? O1 Zn1 O1W 88.54(17) 2_757 2_757 ? O1 Zn1 O1W 91.46(17) . 2_757 ? O1 Zn1 O1W 91.46(17) 2_757 . ? O1 Zn1 O1W 88.54(17) . . ? O1W Zn1 O1W 180 2_757 . ? O1 Zn1 N2 91.73(17) 2_757 2_757 ? O1 Zn1 N2 88.27(17) . 2_757 ? O1W Zn1 N2 93.2(2) 2_757 2_757 ? O1W Zn1 N2 86.8(2) . 2_757 ? O1 Zn1 N2 88.27(17) 2_757 . ? O1 Zn1 N2 91.73(17) . . ? O1W Zn1 N2 86.8(2) 2_757 . ? O1W Zn1 N2 93.2(2) . . ? N2 Zn1 N2 180 2_757 . ? C2 C1 N1 107.2(6) . . ? C2 C1 C6 122.9(6) . . ? N1 C1 C6 129.9(6) . . ? C1 C2 N2 109.6(5) . . ? C1 C2 C3 121.4(6) . . ? N2 C2 C3 129.0(5) . . ? C4 C3 C2 116.2(6) . . ? C4 C3 H3 121.9 . . ? C2 C3 H3 121.9 . . ? C3 C4 C5 122.2(7) . . ? C3 C4 H4 118.9 . . ? C5 C4 H4 118.9 . . ? C4 C5 C6 120.8(7) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 116.5(7) . . ? C1 C6 H6 121.7 . . ? C5 C6 H6 121.7 . . ? N2 C7 N1 111.5(5) . . ? N2 C7 C8 126.6(6) . . ? N1 C7 C8 121.9(6) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 C10 113.2(6) . . ? N1 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? N1 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C10 C10 C9 124(3) 2_658 . ? C10 C10 H10A 106.2 2_658 . ? C9 C10 H10A 106.2 . . ? C10 C10 H10B 106.2 2_658 . ? C9 C10 H10B 106.2 . . ? H10A C10 H10B 106.4 . . ? O2 C11 O1 126.9(6) . . ? O2 C11 C12 116.2(6) . . ? O1 C11 C12 116.8(5) . . ? C16 C12 C13 118.7(5) . . ? C16 C12 C11 120.4(5) . . ? C13 C12 C11 120.9(5) . . ? N3 C13 C12 123.8(6) . . ? N3 C13 H13 118.1 . . ? C12 C13 H13 118.1 . . ? C15 C14 C16 119.3(6) . . ? C15 C14 H14 120.4 . . ? C16 C14 H14 120.4 . . ? N3 C15 C14 123.8(6) . . ? N3 C15 H15 118.1 . . ? C14 C15 H15 118.1 . . ? C12 C16 C14 117.0(6) . . ? C12 C16 H16 121.5 . . ? C14 C16 H16 121.5 . . ? C7 N1 C1 106.2(5) . . ? C7 N1 C9 129.1(6) . . ? C1 N1 C9 124.7(6) . . ? C7 N2 C2 105.5(5) . . ? C7 N2 Zn1 129.1(4) . . ? C2 N2 Zn1 124.8(4) . . ? C15 N3 C13 117.5(6) . . ? C11 O1 Zn1 124.9(4) . . ? Zn1 O1W H1A 88(6) . . ? Zn1 O1W H1B 151(7) . . ? H1A O1W H1B 113(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 1.5(6) . . . . ? C6 C1 C2 N2 -179.4(6) . . . . ? N1 C1 C2 C3 180 . . . . ? C6 C1 C2 C3 -0.9(9) . . . . ? C1 C2 C3 C4 0.9(9) . . . . ? N2 C2 C3 C4 179.1(6) . . . . ? C2 C3 C4 C5 -1.2(10) . . . . ? C3 C4 C5 C6 1.4(12) . . . . ? C2 C1 C6 C5 1.0(10) . . . . ? N1 C1 C6 C5 180.0(7) . . . . ? C4 C5 C6 C1 -1.3(11) . . . . ? N1 C9 C10 C10 58(4) . . . 2_658 ? O2 C11 C12 C16 0.3(9) . . . . ? O1 C11 C12 C16 179.9(6) . . . . ? O2 C11 C12 C13 -177.0(6) . . . . ? O1 C11 C12 C13 2.6(8) . . . . ? C16 C12 C13 N3 -1.0(10) . . . . ? C11 C12 C13 N3 176.3(6) . . . . ? C16 C14 C15 N3 -2.0(13) . . . . ? C13 C12 C16 C14 -0.1(10) . . . . ? C11 C12 C16 C14 -177.5(6) . . . . ? C15 C14 C16 C12 1.5(11) . . . . ? N2 C7 N1 C1 -0.1(7) . . . . ? C8 C7 N1 C1 -179.8(6) . . . . ? N2 C7 N1 C9 177.8(5) . . . . ? C8 C7 N1 C9 -1.9(10) . . . . ? C2 C1 N1 C7 -0.8(6) . . . . ? C6 C1 N1 C7 -179.9(6) . . . . ? C2 C1 N1 C9 -178.8(5) . . . . ? C6 C1 N1 C9 2.1(10) . . . . ? C10 C9 N1 C7 -100.3(16) . . . . ? C10 C9 N1 C1 77.2(17) . . . . ? N1 C7 N2 C2 1.0(6) . . . . ? C8 C7 N2 C2 -179.4(7) . . . . ? N1 C7 N2 Zn1 -170.6(4) . . . . ? C8 C7 N2 Zn1 9.0(9) . . . . ? C1 C2 N2 C7 -1.5(6) . . . . ? C3 C2 N2 C7 -179.9(6) . . . . ? C1 C2 N2 Zn1 170.6(4) . . . . ? C3 C2 N2 Zn1 -7.8(8) . . . . ? O1 Zn1 N2 C7 131.4(5) 2_757 . . . ? O1 Zn1 N2 C7 -48.6(5) . . . . ? O1W Zn1 N2 C7 42.7(5) 2_757 . . . ? O1W Zn1 N2 C7 -137.3(5) . . . . ? O1 Zn1 N2 C2 -38.8(4) 2_757 . . . ? O1 Zn1 N2 C2 141.2(4) . . . . ? O1W Zn1 N2 C2 -127.4(4) 2_757 . . . ? O1W Zn1 N2 C2 52.6(4) . . . . ? C14 C15 N3 C13 0.9(12) . . . . ? C12 C13 N3 C15 0.7(10) . . . . ? O2 C11 O1 Zn1 1.5(9) . . . . ? C12 C11 O1 Zn1 -178.1(4) . . . . ? O1W Zn1 O1 C11 -164.3(5) 2_757 . . . ? O1W Zn1 O1 C11 15.7(5) . . . . ? N2 Zn1 O1 C11 102.6(5) 2_757 . . . ? N2 Zn1 O1 C11 -77.4(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1B N3 0.86(2) 2.25(9) 2.835(7) 125(9) 1_565 _diffrn_measured_fraction_theta_max 0.831 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.902 _refine_diff_density_min -0.841 _refine_diff_density_rms 0.125 #==== data_5 _database_code_depnum_ccdc_archive 'CCDC 806437' #TrackingRef '- crystals.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H28 N8 O12 Zn' _chemical_formula_weight 806.01 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 ' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.800(3) _cell_length_b 12.756(6) _cell_length_c 16.818(5) _cell_angle_alpha 71.521(3) _cell_angle_beta 88.204(2) _cell_angle_gamma 70.909(5) _cell_volume 1878.2(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8525 _cell_measurement_theta_min 4.2 _cell_measurement_theta_max 29.2 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 828 _exptl_absorpt_coefficient_mu 0.726 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7905 _exptl_absorpt_correction_T_max 0.8927 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13847 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.17 _diffrn_reflns_theta_max 29.22 _reflns_number_total 8525 _reflns_number_gt 6495 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. For the nitro groups, N and O atoms are out of the benzene ring plane, which led us to use the FLAT restraint for c31 n6 o7 o8 and c33 n5 o5 o6 atoms, restpcetively. For n5, n6, o5, o6, o7, o8, o3 and c33 some anisotropic displacement ellipsoids were rather elongated which led us to use the ISOR/DELU restraints. ; _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^)+(0.1674P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.064(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8525 _refine_ls_number_parameters 500 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.0998 _refine_ls_R_factor_gt 0.0811 _refine_ls_wR_factor_ref 0.2414 _refine_ls_wR_factor_gt 0.2252 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.106 _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 0.50986(4) 0.26786(3) 0.78133(2) 0.0338(2) Uani 1 1 d . . . C1 C 0.3213(8) 0.2574(6) 0.6090(4) 0.0808(16) Uani 1 1 d . . . H1A H 0.3979 0.2105 0.5851 0.121 Uiso 1 1 calc R . . H1B H 0.2297 0.2697 0.5823 0.121 Uiso 1 1 calc R . . H1C H 0.3240 0.2176 0.6682 0.121 Uiso 1 1 calc R . . C2 C 0.3401(6) 0.3699(5) 0.5960(3) 0.0617(12) Uani 1 1 d . . . C3 C 0.3260(6) 0.5541(5) 0.5364(3) 0.0600(11) Uani 1 1 d . . . C4 C 0.4070(5) 0.5072(4) 0.6143(3) 0.0585(11) Uani 1 1 d . . . C5 C 0.3023(6) 0.6684(5) 0.4847(4) 0.0706(14) Uani 1 1 d . . . H5 H 0.2483 0.6984 0.4331 0.085 Uiso 1 1 calc R . . C6 C 0.3605(8) 0.7347(6) 0.5120(4) 0.0822(17) Uani 1 1 d . . . H6 H 0.3465 0.8118 0.4789 0.099 Uiso 1 1 calc R . . C7 C 0.4423(7) 0.6880(6) 0.5902(4) 0.0769(15) Uani 1 1 d . . . H7 H 0.4818 0.7354 0.6071 0.092 Uiso 1 1 calc R . . C8 C 0.4651(6) 0.5786(5) 0.6409(4) 0.0672(13) Uani 1 1 d . . . H8 H 0.5182 0.5504 0.6927 0.081 Uiso 1 1 calc R . . C9 C 0.1897(6) 0.4761(6) 0.4567(3) 0.0706(14) Uani 1 1 d . . . H9A H 0.2043 0.3987 0.4533 0.085 Uiso 1 1 calc R . . H9B H 0.2180 0.5214 0.4049 0.085 Uiso 1 1 calc R . . C10 C 0.0316(6) 0.5340(5) 0.4634(3) 0.0712(14) Uani 1 1 d . . . H10A H -0.0217 0.5462 0.4118 0.085 Uiso 1 1 calc R . . H10B H 0.0177 0.6105 0.4683 0.085 Uiso 1 1 calc R . . C11 C 0.3941(10) 0.0138(7) 0.8879(6) 0.111(3) Uani 1 1 d . . . H11A H 0.4863 0.0217 0.8960 0.167 Uiso 1 1 calc R . . H11B H 0.3995 -0.0260 0.8474 0.167 Uiso 1 1 calc R . . H11C H 0.3690 -0.0307 0.9404 0.167 Uiso 1 1 calc R . . C12 C 0.2817(7) 0.1320(6) 0.8567(4) 0.0753(15) Uani 1 1 d . . . C13 C 0.1724(6) 0.3184(5) 0.8022(3) 0.0640(12) Uani 1 1 d . . . C14 C 0.1338(7) 0.4395(5) 0.7663(4) 0.0721(14) Uani 1 1 d . . . H16 H 0.2048 0.4745 0.7528 0.087 Uiso 1 1 calc R . . C15 C -0.0098(8) 0.5063(7) 0.7510(4) 0.0895(19) Uani 1 1 d . . . H15 H -0.0358 0.5874 0.7275 0.107 Uiso 1 1 calc R . . C16 C -0.1175(8) 0.4556(8) 0.7698(5) 0.095(2) Uani 1 1 d . . . H14 H -0.2142 0.5032 0.7584 0.114 Uiso 1 1 calc R . . C17 C -0.0829(7) 0.3342(7) 0.8056(4) 0.0867(18) Uani 1 1 d . . . H13 H -0.1542 0.2993 0.8176 0.104 Uiso 1 1 calc R . . C18 C 0.0668(7) 0.2668(6) 0.8226(4) 0.0730(15) Uani 1 1 d . . . C19 C 0.0674(10) 0.0593(7) 0.8925(4) 0.093(2) Uani 1 1 d . . . H52A H -0.0236 0.0814 0.8601 0.112 Uiso 1 1 calc R . . H52B H 0.1297 -0.0150 0.8880 0.112 Uiso 1 1 calc R . . C20 C 0.0398(9) 0.0443(7) 0.9820(4) 0.089(2) Uani 1 1 d . . . H53A H -0.0178 0.1196 0.9870 0.107 Uiso 1 1 calc R . . H53B H 0.1314 0.0178 1.0149 0.107 Uiso 1 1 calc R . . C21 C 0.7214(7) 0.1137(5) 0.7295(3) 0.0701(14) Uani 1 1 d . . . C22 C 0.8323(7) 0.0382(5) 0.6881(3) 0.0673(13) Uani 1 1 d . . . C23 C 0.9670(7) 0.0492(5) 0.6780(3) 0.0674(13) Uani 1 1 d . . . H19 H 0.9906 0.1015 0.6982 0.081 Uiso 1 1 calc R . . C24 C 1.0661(7) -0.0156(5) 0.6388(4) 0.0760(15) Uani 1 1 d . . . C25 C 1.0323(8) -0.0930(6) 0.6045(4) 0.0839(17) Uani 1 1 d . . . H26 H 1.0972 -0.1335 0.5740 0.101 Uiso 1 1 calc R . . C26 C 0.9004(8) -0.1050(5) 0.6183(4) 0.0764(15) Uani 1 1 d . . . C27 C 0.7987(8) -0.0415(6) 0.6591(4) 0.0768(16) Uani 1 1 d . . . H21 H 0.7091 -0.0520 0.6671 0.092 Uiso 1 1 calc R . . C28 C 0.5903(7) 0.3402(6) 0.9011(4) 0.0731(15) Uani 1 1 d . . . N1 N 0.2846(5) 0.4642(4) 0.5274(3) 0.0639(10) Uani 1 1 d . . . N2 N 0.4137(5) 0.3928(4) 0.6505(3) 0.0601(10) Uani 1 1 d . . . N3 N 0.3057(5) 0.2310(4) 0.8244(3) 0.0686(11) Uani 1 1 d . . . N4 N 0.1367(6) 0.1498(5) 0.8564(3) 0.0825(14) Uani 1 1 d . . . N7 N 1.2074(8) -0.0049(6) 0.6285(5) 0.0991(18) Uani 1 1 d . . . N8 N 0.8613(10) -0.1838(6) 0.5845(5) 0.108(2) Uani 1 1 d . . . O1 O 0.6059(6) 0.0928(4) 0.7462(3) 0.0933(13) Uani 1 1 d . . . O2 O 0.7459(5) 0.1958(4) 0.7423(3) 0.0910(13) Uani 1 1 d . . . O3 O 0.6149(6) 0.2341(5) 0.9237(3) 0.0964(14) Uani 1 1 d U . . O4 O 0.5305(7) 0.4109(5) 0.8332(3) 0.0984(15) Uani 1 1 d . . . O9 O 1.2515(9) 0.0309(7) 0.6809(5) 0.139(2) Uani 1 1 d . . . O10 O 1.2768(8) -0.0340(6) 0.5728(5) 0.129(2) Uani 1 1 d . . . O11 O 0.9451(9) -0.2246(7) 0.5373(6) 0.157(3) Uani 1 1 d . . . O12 O 0.7528(9) -0.2097(7) 0.6057(5) 0.138(3) Uani 1 1 d . . . C29 C 0.6534(7) 0.3870(6) 0.9589(4) 0.0726(14) Uani 1 1 d . . . C30 C 0.6995(13) 0.3187(7) 1.0395(6) 0.119(3) Uani 1 1 d . . . H30 H 0.6897 0.2449 1.0599 0.142 Uiso 1 1 calc R . . C31 C 0.7620(17) 0.3596(8) 1.0918(6) 0.157(6) Uani 1 1 d D . . C32 C 0.7767(13) 0.4637(9) 1.0659(7) 0.125(3) Uani 1 1 d . . . H32 H 0.8217 0.4885 1.1008 0.150 Uiso 1 1 calc R . . C33 C 0.7215(11) 0.5368(8) 0.9826(5) 0.098(2) Uani 1 1 d DU . . C34 C 0.6569(9) 0.5015(7) 0.9315(4) 0.0881(19) Uani 1 1 d . . . H34 H 0.6151 0.5527 0.8786 0.106 Uiso 1 1 calc R . . N5 N 0.7274(14) 0.6500(11) 0.9572(8) 0.165(3) Uani 1 1 d DU . . N6 N 0.7879(15) 0.2802(13) 1.1816(10) 0.187(4) Uani 1 1 d DU . . O7 O 0.8524(14) 0.3142(11) 1.2302(8) 0.208(4) Uani 1 1 d DU . . O6 O 0.6581(15) 0.7290(11) 0.8870(8) 0.207(4) Uani 1 1 d DU . . O5 O 0.8113(14) 0.6789(10) 0.9983(7) 0.204(4) Uani 1 1 d DU . . O8 O 0.7563(16) 0.1956(13) 1.2105(9) 0.233(5) Uani 1 1 d DU . . 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 0.0276(3) 0.0393(3) 0.0354(3) -0.01021(17) 0.00087(15) -0.01401(17) C1 0.073(4) 0.085(4) 0.094(4) -0.040(3) -0.005(3) -0.026(3) C2 0.053(3) 0.073(3) 0.061(3) -0.026(2) 0.005(2) -0.019(2) C3 0.050(3) 0.071(3) 0.059(3) -0.024(2) 0.012(2) -0.019(2) C4 0.048(3) 0.064(3) 0.065(3) -0.023(2) 0.015(2) -0.020(2) C5 0.062(3) 0.080(4) 0.059(3) -0.014(2) 0.007(2) -0.017(3) C6 0.083(4) 0.076(4) 0.084(4) -0.015(3) 0.010(3) -0.032(3) C7 0.078(4) 0.074(4) 0.086(4) -0.025(3) 0.009(3) -0.036(3) C8 0.060(3) 0.079(3) 0.067(3) -0.026(3) 0.003(2) -0.026(3) C9 0.066(3) 0.090(4) 0.058(3) -0.035(3) 0.002(2) -0.019(3) C10 0.062(3) 0.085(4) 0.065(3) -0.029(3) -0.010(2) -0.015(3) C11 0.114(7) 0.092(5) 0.109(6) -0.002(4) 0.015(5) -0.039(5) C12 0.076(4) 0.088(4) 0.068(3) -0.017(3) 0.016(3) -0.044(3) C13 0.059(3) 0.086(4) 0.061(3) -0.034(2) 0.014(2) -0.032(3) C14 0.067(4) 0.076(4) 0.077(3) -0.028(3) 0.015(3) -0.027(3) C15 0.076(4) 0.109(5) 0.082(4) -0.042(4) 0.012(3) -0.020(4) C16 0.067(4) 0.131(7) 0.086(4) -0.047(4) 0.006(3) -0.019(4) C17 0.061(4) 0.117(6) 0.096(4) -0.047(4) 0.022(3) -0.037(4) C18 0.076(4) 0.092(4) 0.069(3) -0.033(3) 0.019(3) -0.047(3) C19 0.116(6) 0.106(5) 0.090(4) -0.034(4) 0.028(4) -0.078(5) C20 0.096(5) 0.104(5) 0.084(4) -0.023(3) 0.024(3) -0.063(4) C21 0.069(4) 0.073(3) 0.064(3) -0.023(2) -0.004(2) -0.016(3) C22 0.068(3) 0.062(3) 0.063(3) -0.017(2) -0.001(2) -0.013(3) C23 0.075(4) 0.062(3) 0.068(3) -0.024(2) 0.000(3) -0.022(3) C24 0.075(4) 0.062(3) 0.084(4) -0.017(3) 0.012(3) -0.021(3) C25 0.088(5) 0.078(4) 0.084(4) -0.035(3) 0.009(3) -0.017(3) C26 0.078(4) 0.068(3) 0.084(4) -0.032(3) 0.002(3) -0.018(3) C27 0.072(4) 0.078(4) 0.079(4) -0.023(3) -0.003(3) -0.026(3) C28 0.077(4) 0.090(4) 0.058(3) -0.028(3) 0.008(3) -0.032(3) N1 0.053(2) 0.080(3) 0.059(2) -0.028(2) 0.0023(18) -0.017(2) N2 0.053(2) 0.070(3) 0.060(2) -0.0216(19) 0.0034(17) -0.022(2) N3 0.069(3) 0.075(3) 0.064(2) -0.018(2) 0.007(2) -0.031(2) N4 0.086(4) 0.091(4) 0.083(3) -0.027(3) 0.028(3) -0.048(3) N7 0.090(5) 0.086(4) 0.127(5) -0.034(4) 0.011(4) -0.038(3) N8 0.123(6) 0.081(4) 0.124(5) -0.054(4) -0.012(4) -0.016(4) O1 0.077(3) 0.086(3) 0.118(4) -0.039(3) 0.020(3) -0.026(2) O2 0.076(3) 0.099(3) 0.113(3) -0.063(3) 0.006(2) -0.020(2) O3 0.0985(16) 0.0964(16) 0.0962(16) -0.0339(10) 0.0061(10) -0.0324(10) O4 0.120(4) 0.109(3) 0.068(3) -0.023(2) -0.016(2) -0.044(3) O9 0.132(6) 0.147(6) 0.183(7) -0.077(5) 0.039(5) -0.084(5) O10 0.102(4) 0.139(5) 0.156(6) -0.072(5) 0.061(4) -0.038(4) O11 0.150(7) 0.170(6) 0.207(8) -0.144(6) 0.042(6) -0.048(5) O12 0.135(6) 0.158(6) 0.185(7) -0.102(6) 0.049(5) -0.090(5) C29 0.075(4) 0.080(4) 0.066(3) -0.032(3) 0.000(3) -0.022(3) C30 0.169(9) 0.080(5) 0.106(6) -0.031(4) -0.043(6) -0.036(5) C31 0.252(15) 0.085(5) 0.102(6) -0.026(5) -0.080(8) -0.010(7) C32 0.156(9) 0.104(6) 0.139(8) -0.061(6) -0.026(6) -0.049(6) C33 0.130(7) 0.101(5) 0.073(4) -0.034(4) 0.009(4) -0.049(5) C34 0.099(5) 0.105(5) 0.060(3) -0.025(3) 0.007(3) -0.036(4) N5 0.166(4) 0.164(3) 0.165(4) -0.0533(14) 0.0125(11) -0.0565(15) N6 0.187(4) 0.187(4) 0.187(4) -0.0608(17) 0.0138(11) -0.0626(17) O7 0.209(4) 0.208(4) 0.208(4) -0.0684(16) 0.0153(11) -0.0696(16) O6 0.208(4) 0.207(4) 0.207(4) -0.0668(16) 0.0154(11) -0.0697(17) O5 0.205(4) 0.204(4) 0.204(4) -0.0664(16) 0.0150(11) -0.0696(16) O8 0.233(5) 0.232(5) 0.233(5) -0.0750(18) 0.0183(11) -0.0789(19) _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 N3 2.249(5) . ? Zn1 N2 2.279(4) . ? Zn1 O4 2.322(5) . ? Zn1 O2 2.350(5) . ? Zn1 O1 2.376(5) . ? Zn1 O3 2.488(5) . ? C1 C2 1.454(8) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N2 1.339(6) . ? C2 N1 1.344(7) . ? C3 N1 1.385(7) . ? C3 C5 1.387(8) . ? C3 C4 1.402(7) . ? C4 N2 1.371(7) . ? C4 C8 1.403(7) . ? C5 C6 1.353(10) . ? C5 H5 0.9300 . ? C6 C7 1.408(9) . ? C6 H6 0.9300 . ? C7 C8 1.334(8) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 N1 1.472(7) . ? C9 C10 1.500(8) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C10 1.510(13) 2_566 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.487(11) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N3 1.303(7) . ? C12 N4 1.364(8) . ? C13 C18 1.379(8) . ? C13 N3 1.380(8) . ? C13 C14 1.390(9) . ? C14 C15 1.369(9) . ? C14 H16 0.9300 . ? C15 C16 1.389(11) . ? C15 H15 0.9300 . ? C16 C17 1.398(11) . ? C16 H14 0.9300 . ? C17 C18 1.421(10) . ? C17 H13 0.9300 . ? C18 N4 1.356(9) . ? C19 C20 1.483(9) . ? C19 N4 1.485(7) . ? C19 H52A 0.9700 . ? C19 H52B 0.9700 . ? C20 C20 1.538(11) 2_557 ? C20 H53A 0.9700 . ? C20 H53B 0.9700 . ? C21 O2 1.229(7) . ? C21 O1 1.250(8) . ? C21 C22 1.512(9) . ? C22 C23 1.372(9) . ? C22 C27 1.387(9) . ? C23 C24 1.357(9) . ? C23 H19 0.9300 . ? C24 C25 1.417(9) . ? C24 N7 1.435(10) . ? C25 C26 1.355(10) . ? C25 H26 0.9300 . ? C26 C27 1.380(10) . ? C26 N8 1.451(9) . ? C27 H21 0.9300 . ? C28 O3 1.225(8) . ? C28 O4 1.227(7) . ? C28 C29 1.527(8) . ? N7 O10 1.222(9) . ? N7 O9 1.257(9) . ? N8 O12 1.224(10) . ? N8 O11 1.232(10) . ? C29 C30 1.354(10) . ? C29 C34 1.397(10) . ? C30 C31 1.399(12) . ? C30 H30 0.9300 . ? C31 C32 1.315(14) . ? C31 N6 1.501(17) . ? C32 C33 1.419(13) . ? C32 H32 0.9300 . ? C33 C34 1.345(10) . ? C33 N5 1.390(14) . ? C34 H34 0.9300 . ? N5 O5 1.298(14) . ? N5 O6 1.311(14) . ? N6 O8 1.173(16) . ? N6 O7 1.302(16) . ? 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 N3 Zn1 N2 96.11(16) . . ? N3 Zn1 O4 108.0(2) . . ? N2 Zn1 O4 95.74(16) . . ? N3 Zn1 O2 147.26(19) . . ? N2 Zn1 O2 95.82(17) . . ? O4 Zn1 O2 100.96(19) . . ? N3 Zn1 O1 93.34(18) . . ? N2 Zn1 O1 98.03(18) . . ? O4 Zn1 O1 153.1(2) . . ? O2 Zn1 O1 54.81(17) . . ? N3 Zn1 O3 95.94(17) . . ? N2 Zn1 O3 149.54(18) . . ? O4 Zn1 O3 53.89(17) . . ? O2 Zn1 O3 88.89(18) . . ? O1 Zn1 O3 109.06(18) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N2 C2 N1 111.7(5) . . ? N2 C2 C1 124.6(5) . . ? N1 C2 C1 123.7(5) . . ? N1 C3 C5 132.4(5) . . ? N1 C3 C4 105.5(4) . . ? C5 C3 C4 122.1(5) . . ? N2 C4 C3 109.0(4) . . ? N2 C4 C8 132.2(5) . . ? C3 C4 C8 118.8(5) . . ? C6 C5 C3 117.6(5) . . ? C6 C5 H5 121.2 . . ? C3 C5 H5 121.2 . . ? C5 C6 C7 120.6(6) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 122.6(6) . . ? C8 C7 H7 118.7 . . ? C6 C7 H7 118.7 . . ? C7 C8 C4 118.4(5) . . ? C7 C8 H8 120.8 . . ? C4 C8 H8 120.8 . . ? N1 C9 C10 114.0(4) . . ? N1 C9 H9A 108.7 . . ? C10 C9 H9A 108.7 . . ? N1 C9 H9B 108.7 . . ? C10 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C9 C10 C10 114.6(6) . 2_566 ? C9 C10 H10A 108.6 . . ? C10 C10 H10A 108.6 2_566 . ? C9 C10 H10B 108.6 . . ? C10 C10 H10B 108.6 2_566 . ? H10A C10 H10B 107.6 . . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 N4 110.8(6) . . ? N3 C12 C11 125.9(6) . . ? N4 C12 C11 123.2(6) . . ? C18 C13 N3 108.1(5) . . ? C18 C13 C14 120.2(6) . . ? N3 C13 C14 131.7(5) . . ? C15 C14 C13 119.2(6) . . ? C15 C14 H16 120.4 . . ? C13 C14 H16 120.4 . . ? C14 C15 C16 121.3(8) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C15 C16 C17 121.1(7) . . ? C15 C16 H14 119.4 . . ? C17 C16 H14 119.4 . . ? C16 C17 C18 116.5(6) . . ? C16 C17 H13 121.7 . . ? C18 C17 H13 121.7 . . ? N4 C18 C13 106.6(6) . . ? N4 C18 C17 131.8(6) . . ? C13 C18 C17 121.6(6) . . ? C20 C19 N4 112.4(5) . . ? C20 C19 H52A 109.1 . . ? N4 C19 H52A 109.1 . . ? C20 C19 H52B 109.1 . . ? N4 C19 H52B 109.1 . . ? H52A C19 H52B 107.9 . . ? C19 C20 C20 112.4(7) . 2_557 ? C19 C20 H53A 109.1 . . ? C20 C20 H53A 109.1 2_557 . ? C19 C20 H53B 109.1 . . ? C20 C20 H53B 109.1 2_557 . ? H53A C20 H53B 107.8 . . ? O2 C21 O1 122.7(6) . . ? O2 C21 C22 118.8(6) . . ? O1 C21 C22 118.4(6) . . ? C23 C22 C27 119.4(6) . . ? C23 C22 C21 120.0(5) . . ? C27 C22 C21 120.6(6) . . ? C24 C23 C22 120.7(6) . . ? C24 C23 H19 119.7 . . ? C22 C23 H19 119.7 . . ? C23 C24 C25 121.3(6) . . ? C23 C24 N7 120.9(6) . . ? C25 C24 N7 117.8(6) . . ? C26 C25 C24 116.5(6) . . ? C26 C25 H26 121.8 . . ? C24 C25 H26 121.8 . . ? C25 C26 C27 123.2(6) . . ? C25 C26 N8 118.4(7) . . ? C27 C26 N8 118.4(7) . . ? C26 C27 C22 118.9(6) . . ? C26 C27 H21 120.6 . . ? C22 C27 H21 120.6 . . ? O3 C28 O4 126.0(6) . . ? O3 C28 C29 117.0(6) . . ? O4 C28 C29 116.8(6) . . ? C2 N1 C3 107.6(4) . . ? C2 N1 C9 127.8(5) . . ? C3 N1 C9 124.5(5) . . ? C2 N2 C4 106.2(4) . . ? C2 N2 Zn1 125.2(4) . . ? C4 N2 Zn1 128.4(3) . . ? C12 N3 C13 107.1(5) . . ? C12 N3 Zn1 130.7(4) . . ? C13 N3 Zn1 121.0(3) . . ? C18 N4 C12 107.4(5) . . ? C18 N4 C19 126.0(6) . . ? C12 N4 C19 126.5(6) . . ? O10 N7 O9 125.1(8) . . ? O10 N7 C24 119.1(7) . . ? O9 N7 C24 115.7(7) . . ? O12 N8 O11 123.5(7) . . ? O12 N8 C26 120.0(8) . . ? O11 N8 C26 116.5(8) . . ? C21 O1 Zn1 90.2(4) . . ? C21 O2 Zn1 91.9(4) . . ? C28 O3 Zn1 86.2(4) . . ? C28 O4 Zn1 93.9(4) . . ? C30 C29 C34 119.3(6) . . ? C30 C29 C28 119.4(6) . . ? C34 C29 C28 121.2(5) . . ? C29 C30 C31 119.7(8) . . ? C29 C30 H30 120.2 . . ? C31 C30 H30 120.2 . . ? C32 C31 C30 122.3(8) . . ? C32 C31 N6 124.7(10) . . ? C30 C31 N6 112.4(11) . . ? C31 C32 C33 117.5(7) . . ? C31 C32 H32 121.2 . . ? C33 C32 H32 121.2 . . ? C34 C33 N5 120.6(9) . . ? C34 C33 C32 121.7(8) . . ? N5 C33 C32 117.6(8) . . ? C33 C34 C29 119.1(7) . . ? C33 C34 H34 120.4 . . ? C29 C34 H34 120.4 . . ? O5 N5 O6 117.1(13) . . ? O5 N5 C33 121.2(12) . . ? O6 N5 C33 121.4(12) . . ? O8 N6 O7 119.1(17) . . ? O8 N6 C31 127.8(16) . . ? O7 N6 C31 113.0(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C3 C4 N2 0.1(5) . . . . ? C5 C3 C4 N2 -179.2(5) . . . . ? N1 C3 C4 C8 179.7(5) . . . . ? C5 C3 C4 C8 0.4(8) . . . . ? N1 C3 C5 C6 -179.1(6) . . . . ? C4 C3 C5 C6 0.0(8) . . . . ? C3 C5 C6 C7 0.1(10) . . . . ? C5 C6 C7 C8 -0.7(11) . . . . ? C6 C7 C8 C4 1.0(10) . . . . ? N2 C4 C8 C7 178.6(6) . . . . ? C3 C4 C8 C7 -0.9(8) . . . . ? N1 C9 C10 C10 -64.6(8) . . . 2_566 ? C18 C13 C14 C15 -0.3(9) . . . . ? N3 C13 C14 C15 -179.8(6) . . . . ? C13 C14 C15 C16 -0.7(9) . . . . ? C14 C15 C16 C17 0.4(10) . . . . ? C15 C16 C17 C18 0.9(10) . . . . ? N3 C13 C18 N4 -0.1(6) . . . . ? C14 C13 C18 N4 -179.7(5) . . . . ? N3 C13 C18 C17 -178.6(5) . . . . ? C14 C13 C18 C17 1.8(8) . . . . ? C16 C17 C18 N4 179.8(7) . . . . ? C16 C17 C18 C13 -2.0(9) . . . . ? N4 C19 C20 C20 176.7(8) . . . 2_557 ? O2 C21 C22 C23 10.6(8) . . . . ? O1 C21 C22 C23 -172.2(5) . . . . ? O2 C21 C22 C27 -168.6(5) . . . . ? O1 C21 C22 C27 8.6(8) . . . . ? C27 C22 C23 C24 1.1(8) . . . . ? C21 C22 C23 C24 -178.1(5) . . . . ? C22 C23 C24 C25 2.4(9) . . . . ? C22 C23 C24 N7 -179.7(6) . . . . ? C23 C24 C25 C26 -4.7(9) . . . . ? N7 C24 C25 C26 177.3(6) . . . . ? C24 C25 C26 C27 3.7(10) . . . . ? C24 C25 C26 N8 -179.8(6) . . . . ? C25 C26 C27 C22 -0.4(10) . . . . ? N8 C26 C27 C22 -176.9(6) . . . . ? C23 C22 C27 C26 -2.1(9) . . . . ? C21 C22 C27 C26 177.1(5) . . . . ? N2 C2 N1 C3 1.1(6) . . . . ? C1 C2 N1 C3 -179.2(5) . . . . ? N2 C2 N1 C9 -175.6(5) . . . . ? C1 C2 N1 C9 4.2(9) . . . . ? C5 C3 N1 C2 178.5(6) . . . . ? C4 C3 N1 C2 -0.7(6) . . . . ? C5 C3 N1 C9 -4.7(9) . . . . ? C4 C3 N1 C9 176.1(5) . . . . ? C10 C9 N1 C2 97.3(7) . . . . ? C10 C9 N1 C3 -78.8(7) . . . . ? N1 C2 N2 C4 -1.0(6) . . . . ? C1 C2 N2 C4 179.2(6) . . . . ? N1 C2 N2 Zn1 173.9(3) . . . . ? C1 C2 N2 Zn1 -5.8(8) . . . . ? C3 C4 N2 C2 0.6(5) . . . . ? C8 C4 N2 C2 -179.0(6) . . . . ? C3 C4 N2 Zn1 -174.2(3) . . . . ? C8 C4 N2 Zn1 6.3(8) . . . . ? N3 Zn1 N2 C2 -51.8(4) . . . . ? O4 Zn1 N2 C2 -160.6(4) . . . . ? O2 Zn1 N2 C2 97.7(4) . . . . ? O1 Zn1 N2 C2 42.5(4) . . . . ? O3 Zn1 N2 C2 -164.6(4) . . . . ? N3 Zn1 N2 C4 122.0(4) . . . . ? O4 Zn1 N2 C4 13.2(4) . . . . ? O2 Zn1 N2 C4 -88.5(4) . . . . ? O1 Zn1 N2 C4 -143.7(4) . . . . ? O3 Zn1 N2 C4 9.2(6) . . . . ? N4 C12 N3 C13 0.4(7) . . . . ? C11 C12 N3 C13 178.7(7) . . . . ? N4 C12 N3 Zn1 -166.5(4) . . . . ? C11 C12 N3 Zn1 11.9(10) . . . . ? C18 C13 N3 C12 -0.2(6) . . . . ? C14 C13 N3 C12 179.3(6) . . . . ? C18 C13 N3 Zn1 168.2(4) . . . . ? C14 C13 N3 Zn1 -12.3(8) . . . . ? N2 Zn1 N3 C12 127.3(5) . . . . ? O4 Zn1 N3 C12 -134.6(5) . . . . ? O2 Zn1 N3 C12 16.5(7) . . . . ? O1 Zn1 N3 C12 28.8(5) . . . . ? O3 Zn1 N3 C12 -80.7(5) . . . . ? N2 Zn1 N3 C13 -38.0(4) . . . . ? O4 Zn1 N3 C13 60.1(4) . . . . ? O2 Zn1 N3 C13 -148.8(4) . . . . ? O1 Zn1 N3 C13 -136.4(4) . . . . ? O3 Zn1 N3 C13 114.0(4) . . . . ? C13 C18 N4 C12 0.3(7) . . . . ? C17 C18 N4 C12 178.6(6) . . . . ? C13 C18 N4 C19 176.0(5) . . . . ? C17 C18 N4 C19 -5.6(11) . . . . ? N3 C12 N4 C18 -0.4(7) . . . . ? C11 C12 N4 C18 -178.8(7) . . . . ? N3 C12 N4 C19 -176.1(6) . . . . ? C11 C12 N4 C19 5.5(10) . . . . ? C20 C19 N4 C18 -85.4(9) . . . . ? C20 C19 N4 C12 89.5(9) . . . . ? C23 C24 N7 O10 -157.6(7) . . . . ? C25 C24 N7 O10 20.4(10) . . . . ? C23 C24 N7 O9 24.8(10) . . . . ? C25 C24 N7 O9 -157.2(7) . . . . ? C25 C26 N8 O12 169.5(8) . . . . ? C27 C26 N8 O12 -13.8(11) . . . . ? C25 C26 N8 O11 -7.9(11) . . . . ? C27 C26 N8 O11 168.8(8) . . . . ? O2 C21 O1 Zn1 6.1(6) . . . . ? C22 C21 O1 Zn1 -171.0(4) . . . . ? N3 Zn1 O1 C21 -175.1(4) . . . . ? N2 Zn1 O1 C21 88.2(4) . . . . ? O4 Zn1 O1 C21 -31.9(6) . . . . ? O2 Zn1 O1 C21 -3.3(3) . . . . ? O3 Zn1 O1 C21 -77.7(4) . . . . ? O1 C21 O2 Zn1 -6.2(6) . . . . ? C22 C21 O2 Zn1 170.9(4) . . . . ? N3 Zn1 O2 C21 18.5(5) . . . . ? N2 Zn1 O2 C21 -92.4(4) . . . . ? O4 Zn1 O2 C21 170.6(4) . . . . ? O1 Zn1 O2 C21 3.3(3) . . . . ? O3 Zn1 O2 C21 117.8(4) . . . . ? O4 C28 O3 Zn1 2.8(7) . . . . ? C29 C28 O3 Zn1 -170.5(5) . . . . ? N3 Zn1 O3 C28 -109.5(4) . . . . ? N2 Zn1 O3 C28 3.4(6) . . . . ? O4 Zn1 O3 C28 -1.5(4) . . . . ? O2 Zn1 O3 C28 103.0(4) . . . . ? O1 Zn1 O3 C28 154.9(4) . . . . ? O3 C28 O4 Zn1 -3.0(8) . . . . ? C29 C28 O4 Zn1 170.3(5) . . . . ? N3 Zn1 O4 C28 85.6(4) . . . . ? N2 Zn1 O4 C28 -176.1(4) . . . . ? O2 Zn1 O4 C28 -79.0(4) . . . . ? O1 Zn1 O4 C28 -55.5(6) . . . . ? O3 Zn1 O4 C28 1.5(4) . . . . ? O3 C28 C29 C30 -16.7(11) . . . . ? O4 C28 C29 C30 169.4(8) . . . . ? O3 C28 C29 C34 167.0(7) . . . . ? O4 C28 C29 C34 -6.9(10) . . . . ? C34 C29 C30 C31 -5.8(16) . . . . ? C28 C29 C30 C31 177.8(10) . . . . ? C29 C30 C31 C32 1(2) . . . . ? C29 C30 C31 N6 172.2(10) . . . . ? C30 C31 C32 C33 2(2) . . . . ? N6 C31 C32 C33 -168.0(12) . . . . ? C31 C32 C33 C34 -0.3(17) . . . . ? C31 C32 C33 N5 175.4(12) . . . . ? N5 C33 C34 C29 179.7(8) . . . . ? C32 C33 C34 C29 -4.7(14) . . . . ? C30 C29 C34 C33 7.7(12) . . . . ? C28 C29 C34 C33 -176.0(7) . . . . ? C34 C33 N5 O5 -167.0(11) . . . . ? C32 C33 N5 O5 17.2(15) . . . . ? C34 C33 N5 O6 7.2(16) . . . . ? C32 C33 N5 O6 -168.7(11) . . . . ? C32 C31 N6 O8 167.4(17) . . . . ? C30 C31 N6 O8 -4(2) . . . . ? C32 C31 N6 O7 -12(2) . . . . ? C30 C31 N6 O7 176.9(12) . . . . ? _diffrn_measured_fraction_theta_max 0.836 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.655 _refine_diff_density_min -0.797 _refine_diff_density_rms 0.132 #==== data_6 _database_code_depnum_ccdc_archive 'CCDC 806438' #TrackingRef '- crystals.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H26 N4 O4 Zn' _chemical_formula_weight 547.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.4659(2) _cell_length_b 14.6320(4) _cell_length_c 16.5116(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2528.54(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6329 _cell_measurement_theta_min 4.1 _cell_measurement_theta_max 29.9 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 1.013 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.68 _exptl_absorpt_correction_T_max 0.74 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12908 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0692 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.09 _diffrn_reflns_theta_max 29.88 _reflns_number_total 6329 _reflns_number_gt 4506 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.1181P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.62(3) _refine_ls_number_reflns 6329 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0895 _refine_ls_R_factor_gt 0.0643 _refine_ls_wR_factor_ref 0.1844 _refine_ls_wR_factor_gt 0.1738 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 0.77222(5) 0.12398(3) 1.00651(3) 0.02654(16) Uani 1 1 d . . . C1 C -0.0090(9) -0.1741(6) 1.3744(6) 0.084(3) Uani 1 1 d . . . H1A H -0.0554 -0.2056 1.4160 0.126 Uiso 1 1 calc R . . H1B H 0.0796 -0.1707 1.3890 0.126 Uiso 1 1 calc R . . H1C H -0.0177 -0.2065 1.3242 0.126 Uiso 1 1 calc R . . C2 C -0.0591(7) -0.0837(6) 1.3654(5) 0.0608(19) Uani 1 1 d . . . C3 C -0.1775(7) 0.0386(5) 1.3784(4) 0.0556(17) Uani 1 1 d . . . C4 C -0.0898(7) 0.0569(5) 1.3185(5) 0.0606(18) Uani 1 1 d . . . C5 C -0.2667(8) 0.1054(6) 1.3991(5) 0.078(2) Uani 1 1 d . . . H5 H -0.3249 0.0951 1.4407 0.093 Uiso 1 1 calc R . . C6 C -0.2679(11) 0.1870(7) 1.3573(6) 0.092(3) Uani 1 1 d . . . H6 H -0.3271 0.2318 1.3710 0.110 Uiso 1 1 calc R . . C7 C -0.1830(11) 0.2028(8) 1.2959(7) 0.099(3) Uani 1 1 d . . . H7 H -0.1868 0.2579 1.2679 0.119 Uiso 1 1 calc R . . C8 C -0.0898(9) 0.1379(7) 1.2738(6) 0.083(2) Uani 1 1 d . . . H8 H -0.0320 0.1484 1.2321 0.100 Uiso 1 1 calc R . . C9 C 0.0918(7) -0.0309(7) 1.2555(5) 0.068(2) Uani 1 1 d . . . H9A H 0.0769 0.0051 1.2071 0.082 Uiso 1 1 calc R . . H9B H 0.0997 -0.0945 1.2396 0.082 Uiso 1 1 calc R . . C10 C 0.2185(8) 0.0014(7) 1.2975(5) 0.082(2) Uani 1 1 d . . . H10A H 0.2089 0.0645 1.3144 0.098 Uiso 1 1 calc R . . H10B H 0.2329 -0.0352 1.3456 0.098 Uiso 1 1 calc R . . C11 C 0.3330(7) -0.0063(7) 1.2429(5) 0.078(3) Uani 1 1 d . . . H11A H 0.3417 -0.0695 1.2261 0.094 Uiso 1 1 calc R . . H11B H 0.3175 0.0299 1.1946 0.094 Uiso 1 1 calc R . . C12 C 0.4544(7) 0.0235(8) 1.2792(5) 0.083(3) Uani 1 1 d . . . H12A H 0.4448 0.0861 1.2977 0.100 Uiso 1 1 calc R . . H12B H 0.4715 -0.0141 1.3264 0.100 Uiso 1 1 calc R . . C13 C 0.5411(12) 0.1761(8) 1.1721(8) 0.111(4) Uani 1 1 d . . . H13A H 0.5848 0.2153 1.1347 0.167 Uiso 1 1 calc R . . H13B H 0.5468 0.2014 1.2257 0.167 Uiso 1 1 calc R . . H13C H 0.4530 0.1710 1.1567 0.167 Uiso 1 1 calc R . . C14 C 0.6010(7) 0.0842(6) 1.1712(5) 0.067(2) Uani 1 1 d . . . C15 C 0.6384(8) -0.0576(6) 1.2118(5) 0.068(2) Uani 1 1 d . . . C16 C 0.6442(9) -0.1386(7) 1.2523(6) 0.085(3) Uani 1 1 d . . . H16 H 0.5904 -0.1525 1.2954 0.102 Uiso 1 1 calc R . . C17 C 0.7377(12) -0.1995(7) 1.2238(6) 0.096(3) Uani 1 1 d . . . H17 H 0.7453 -0.2566 1.2480 0.116 Uiso 1 1 calc R . . C18 C 0.8209(12) -0.1761(7) 1.1592(7) 0.101(4) Uani 1 1 d . . . H18 H 0.8822 -0.2181 1.1424 0.121 Uiso 1 1 calc R . . C19 C 0.8132(9) -0.0931(6) 1.1207(5) 0.074(2) Uani 1 1 d . . . H19 H 0.8680 -0.0776 1.0786 0.089 Uiso 1 1 calc R . . C20 C 0.7202(7) -0.0340(6) 1.1478(4) 0.0599(17) Uani 1 1 d . . . C21 C 1.0259(6) 0.0743(4) 1.0140(4) 0.0528(15) Uani 1 1 d . . . C22 C 1.1566(7) 0.0338(5) 1.0148(4) 0.0599(17) Uani 1 1 d . . . C23 C 1.1666(8) -0.0585(5) 1.0111(6) 0.071(2) Uani 1 1 d . . . H23 H 1.0937 -0.0948 1.0116 0.085 Uiso 1 1 calc R . . C24 C 1.2908(9) -0.0994(7) 1.0066(7) 0.101(3) Uani 1 1 d . . . H24 H 1.2989 -0.1621 0.9988 0.121 Uiso 1 1 calc R . . C25 C 1.3962(8) -0.0463(6) 1.0138(7) 0.091(3) Uani 1 1 d . . . H25 H 1.4769 -0.0728 1.0125 0.109 Uiso 1 1 calc R . . C26 C 1.3834(8) 0.0493(6) 1.0231(6) 0.078(2) Uani 1 1 d . . . H26 H 1.4557 0.0852 1.0308 0.094 Uiso 1 1 calc R . . C27 C 1.2644(7) 0.0898(5) 1.0209(4) 0.0617(17) Uani 1 1 d . . . C28 C 1.2591(7) 0.1913(6) 1.0204(5) 0.0656(18) Uani 1 1 d . . . N1 N -0.1599(6) -0.0476(5) 1.4072(4) 0.0609(15) Uani 1 1 d . . . N2 N -0.0150(6) -0.0205(5) 1.3106(4) 0.0661(17) Uani 1 1 d . . . N3 N 0.5625(6) 0.0188(5) 1.2259(4) 0.0703(18) Uani 1 1 d . . . N4 N 0.6917(6) 0.0579(5) 1.1237(4) 0.0678(17) Uani 1 1 d . . . O1 O 0.9928(5) 0.1291(5) 1.0683(4) 0.097(2) Uani 1 1 d . . . O2 O 0.9447(6) 0.0450(6) 0.9655(4) 0.104(2) Uani 1 1 d . . . O3 O 1.2066(7) 0.2296(5) 0.9621(4) 0.098(2) Uani 1 1 d . . . O4 O 1.3087(8) 0.2364(6) 1.0751(6) 0.129(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0208(2) 0.0304(2) 0.0284(2) -0.0014(3) -0.00021(19) -0.00021(19) C1 0.080(6) 0.078(6) 0.094(7) 0.006(5) 0.020(5) 0.015(5) C2 0.062(4) 0.070(5) 0.050(4) 0.005(3) 0.004(3) -0.002(4) C3 0.059(4) 0.061(4) 0.047(4) 0.002(3) 0.005(3) 0.008(3) C4 0.059(4) 0.052(4) 0.071(5) 0.001(4) -0.002(3) 0.000(3) C5 0.076(5) 0.076(6) 0.081(5) -0.001(4) 0.016(4) -0.001(5) C6 0.105(8) 0.067(6) 0.103(7) 0.001(5) 0.029(6) 0.012(5) C7 0.101(7) 0.074(6) 0.122(9) 0.018(6) 0.008(7) -0.015(6) C8 0.091(6) 0.074(6) 0.085(6) 0.013(5) 0.019(4) -0.009(5) C9 0.060(4) 0.088(5) 0.057(4) -0.004(4) 0.009(3) -0.010(4) C10 0.075(5) 0.112(7) 0.057(4) -0.003(4) 0.008(4) -0.020(5) C11 0.052(4) 0.112(8) 0.071(5) -0.005(5) 0.008(4) -0.013(4) C12 0.062(5) 0.135(8) 0.052(4) -0.002(5) 0.009(3) 0.003(5) C13 0.107(8) 0.101(8) 0.126(10) 0.024(7) 0.042(7) 0.008(6) C14 0.057(4) 0.076(5) 0.067(5) 0.009(4) 0.011(3) 0.012(4) C15 0.064(5) 0.077(6) 0.064(5) 0.004(4) 0.003(4) -0.005(4) C16 0.094(7) 0.075(6) 0.086(6) 0.015(5) -0.002(5) -0.007(5) C17 0.132(9) 0.074(6) 0.084(6) 0.018(5) 0.009(6) -0.003(6) C18 0.130(9) 0.082(7) 0.091(7) 0.009(6) 0.004(6) 0.019(6) C19 0.079(5) 0.073(6) 0.070(5) 0.005(4) 0.004(4) 0.019(4) C20 0.057(4) 0.070(5) 0.053(4) 0.001(3) -0.005(3) 0.000(4) C21 0.046(3) 0.059(4) 0.053(4) -0.009(3) 0.005(3) -0.001(3) C22 0.059(4) 0.069(4) 0.052(4) -0.002(4) 0.008(3) 0.007(3) C23 0.072(4) 0.061(4) 0.081(5) 0.004(5) -0.003(4) 0.009(3) C24 0.096(7) 0.066(4) 0.139(10) -0.008(6) -0.017(8) 0.021(4) C25 0.059(5) 0.083(5) 0.130(9) 0.004(7) 0.010(5) 0.013(4) C26 0.066(5) 0.083(5) 0.086(6) 0.014(5) 0.008(4) 0.012(4) C27 0.054(4) 0.066(4) 0.065(4) 0.005(3) -0.001(3) 0.008(3) C28 0.061(4) 0.077(5) 0.059(4) -0.004(4) -0.002(3) -0.002(3) N1 0.067(4) 0.066(4) 0.050(3) 0.000(3) 0.010(3) -0.001(3) N2 0.058(4) 0.076(4) 0.065(4) 0.002(3) 0.012(3) -0.007(3) N3 0.060(4) 0.078(5) 0.073(4) 0.010(4) 0.009(3) 0.002(3) N4 0.056(3) 0.075(4) 0.072(4) 0.004(3) 0.009(3) 0.010(3) O1 0.074(4) 0.106(5) 0.110(5) -0.040(5) 0.005(3) 0.009(4) O2 0.066(4) 0.145(6) 0.101(5) -0.045(5) -0.018(3) 0.005(4) O3 0.113(5) 0.088(4) 0.093(4) 0.007(4) -0.020(4) 0.000(4) O4 0.119(6) 0.108(6) 0.162(7) -0.046(6) -0.062(6) 0.017(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 2.247(6) . ? Zn1 N1 2.306(6) 2_554 ? Zn1 O3 2.308(7) 3_457 ? Zn1 N4 2.322(7) . ? Zn1 O4 2.477(9) 3_457 ? C1 C2 1.430(11) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N1 1.367(9) . ? C2 N2 1.374(9) . ? C3 N1 1.361(10) . ? C3 C4 1.375(10) . ? C3 C5 1.395(11) . ? C4 N2 1.384(10) . ? C4 C8 1.396(12) . ? C5 C6 1.379(13) . ? C5 H5 0.9300 . ? C6 C7 1.368(15) . ? C6 H6 0.9300 . ? C7 C8 1.409(14) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 N2 1.449(9) . ? C9 C10 1.569(11) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.504(11) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.471(12) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N3 1.436(9) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.483(13) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 N4 1.290(10) . ? C14 N3 1.376(10) . ? C15 C16 1.362(12) . ? C15 N3 1.392(11) . ? C15 C20 1.402(11) . ? C16 C17 1.404(13) . ? C16 H16 0.9300 . ? C17 C18 1.420(14) . ? C17 H17 0.9300 . ? C18 C19 1.373(13) . ? C18 H18 0.9300 . ? C19 C20 1.377(11) . ? C19 H19 0.9300 . ? C20 N4 1.433(10) . ? C21 O2 1.244(8) . ? C21 O1 1.251(8) . ? C21 C22 1.491(9) . ? C22 C23 1.355(10) . ? C22 C27 1.399(11) . ? C23 C24 1.433(12) . ? C23 H23 0.9300 . ? C24 C25 1.354(13) . ? C24 H24 0.9300 . ? C25 C26 1.415(12) . ? C25 H25 0.9300 . ? C26 C27 1.379(11) . ? C26 H26 0.9300 . ? C27 C28 1.486(11) . ? C28 O4 1.234(9) . ? C28 O3 1.242(9) . ? N1 Zn1 2.306(6) 2 ? O3 Zn1 2.308(7) 3_557 ? O4 Zn1 2.477(9) 3_557 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Zn1 N1 86.9(2) . 2_554 ? O2 Zn1 O3 141.6(3) . 3_457 ? N1 Zn1 O3 117.2(3) 2_554 3_457 ? O2 Zn1 N4 109.2(3) . . ? N1 Zn1 N4 101.9(2) 2_554 . ? O3 Zn1 N4 95.2(2) 3_457 . ? O2 Zn1 O4 97.8(3) . 3_457 ? N1 Zn1 O4 95.3(3) 2_554 3_457 ? O3 Zn1 O4 53.3(2) 3_457 3_457 ? N4 Zn1 O4 148.5(2) . 3_457 ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 N2 109.4(7) . . ? N1 C2 C1 126.0(7) . . ? N2 C2 C1 124.5(7) . . ? N1 C3 C4 110.0(6) . . ? N1 C3 C5 130.9(7) . . ? C4 C3 C5 119.1(7) . . ? C3 C4 N2 106.6(7) . . ? C3 C4 C8 123.1(8) . . ? N2 C4 C8 130.2(8) . . ? C6 C5 C3 119.3(8) . . ? C6 C5 H5 120.3 . . ? C3 C5 H5 120.3 . . ? C7 C6 C5 120.7(10) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 121.9(10) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C4 C8 C7 115.8(9) . . ? C4 C8 H8 122.1 . . ? C7 C8 H8 122.1 . . ? N2 C9 C10 110.1(6) . . ? N2 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? N2 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C11 C10 C9 112.7(6) . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10B 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 114.9(7) . . ? C12 C11 H11A 108.5 . . ? C10 C11 H11A 108.5 . . ? C12 C11 H11B 108.5 . . ? C10 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? N3 C12 C11 114.6(7) . . ? N3 C12 H12A 108.6 . . ? C11 C12 H12A 108.6 . . ? N3 C12 H12B 108.6 . . ? C11 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N4 C14 N3 114.0(7) . . ? N4 C14 C13 126.0(8) . . ? N3 C14 C13 120.0(7) . . ? C16 C15 N3 130.0(8) . . ? C16 C15 C20 123.9(9) . . ? N3 C15 C20 106.0(7) . . ? C15 C16 C17 114.8(9) . . ? C15 C16 H16 122.6 . . ? C17 C16 H16 122.6 . . ? C16 C17 C18 121.7(9) . . ? C16 C17 H17 119.1 . . ? C18 C17 H17 119.1 . . ? C19 C18 C17 121.7(10) . . ? C19 C18 H18 119.2 . . ? C17 C18 H18 119.2 . . ? C18 C19 C20 116.5(9) . . ? C18 C19 H19 121.7 . . ? C20 C19 H19 121.7 . . ? C19 C20 C15 121.4(8) . . ? C19 C20 N4 130.2(7) . . ? C15 C20 N4 108.2(7) . . ? O2 C21 O1 119.5(6) . . ? O2 C21 C22 119.7(6) . . ? O1 C21 C22 120.2(6) . . ? C23 C22 C27 121.6(7) . . ? C23 C22 C21 117.8(7) . . ? C27 C22 C21 120.5(6) . . ? C22 C23 C24 119.3(8) . . ? C22 C23 H23 120.3 . . ? C24 C23 H23 120.3 . . ? C25 C24 C23 119.6(8) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C26 120.0(8) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C27 C26 C25 120.5(8) . . ? C27 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? C26 C27 C22 118.6(7) . . ? C26 C27 C28 117.6(7) . . ? C22 C27 C28 123.7(7) . . ? O4 C28 O3 120.8(9) . . ? O4 C28 C27 121.0(8) . . ? O3 C28 C27 118.2(7) . . ? C3 N1 C2 106.6(6) . . ? C3 N1 Zn1 129.0(5) . 2 ? C2 N1 Zn1 124.4(5) . 2 ? C2 N2 C4 107.4(6) . . ? C2 N2 C9 127.0(7) . . ? C4 N2 C9 125.6(7) . . ? C14 N3 C15 106.4(6) . . ? C14 N3 C12 126.9(8) . . ? C15 N3 C12 126.2(8) . . ? C14 N4 C20 105.4(7) . . ? C14 N4 Zn1 130.5(6) . . ? C20 N4 Zn1 123.1(5) . . ? C21 O2 Zn1 100.2(5) . . ? C28 O3 Zn1 96.5(5) . 3_557 ? C28 O4 Zn1 88.8(6) . 3_557 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C3 C4 N2 -0.4(9) . . . . ? C5 C3 C4 N2 -179.7(7) . . . . ? N1 C3 C4 C8 175.6(8) . . . . ? C5 C3 C4 C8 -3.7(13) . . . . ? N1 C3 C5 C6 -176.9(9) . . . . ? C4 C3 C5 C6 2.2(13) . . . . ? C3 C5 C6 C7 0.2(17) . . . . ? C5 C6 C7 C8 -1.3(18) . . . . ? C3 C4 C8 C7 2.5(14) . . . . ? N2 C4 C8 C7 177.5(9) . . . . ? C6 C7 C8 C4 0.0(16) . . . . ? N2 C9 C10 C11 -179.1(8) . . . . ? C9 C10 C11 C12 179.8(9) . . . . ? C10 C11 C12 N3 -178.0(8) . . . . ? N3 C15 C16 C17 -176.7(8) . . . . ? C20 C15 C16 C17 -1.5(14) . . . . ? C15 C16 C17 C18 1.6(15) . . . . ? C16 C17 C18 C19 -0.6(17) . . . . ? C17 C18 C19 C20 -0.4(16) . . . . ? C18 C19 C20 C15 0.5(13) . . . . ? C18 C19 C20 N4 176.5(9) . . . . ? C16 C15 C20 C19 0.6(13) . . . . ? N3 C15 C20 C19 176.7(7) . . . . ? C16 C15 C20 N4 -176.3(8) . . . . ? N3 C15 C20 N4 -0.1(9) . . . . ? O2 C21 C22 C23 -44.4(11) . . . . ? O1 C21 C22 C23 126.7(8) . . . . ? O2 C21 C22 C27 137.1(8) . . . . ? O1 C21 C22 C27 -51.9(10) . . . . ? C27 C22 C23 C24 -5.4(14) . . . . ? C21 C22 C23 C24 176.1(9) . . . . ? C22 C23 C24 C25 6.3(17) . . . . ? C23 C24 C25 C26 -2.0(18) . . . . ? C24 C25 C26 C27 -3.3(16) . . . . ? C25 C26 C27 C22 4.3(13) . . . . ? C25 C26 C27 C28 -172.2(9) . . . . ? C23 C22 C27 C26 0.2(12) . . . . ? C21 C22 C27 C26 178.6(7) . . . . ? C23 C22 C27 C28 176.4(8) . . . . ? C21 C22 C27 C28 -5.2(11) . . . . ? C26 C27 C28 O4 -57.6(11) . . . . ? C22 C27 C28 O4 126.2(9) . . . . ? C26 C27 C28 O3 120.4(9) . . . . ? C22 C27 C28 O3 -55.9(11) . . . . ? C4 C3 N1 C2 0.5(8) . . . . ? C5 C3 N1 C2 179.6(9) . . . . ? C4 C3 N1 Zn1 -179.5(5) . . . 2 ? C5 C3 N1 Zn1 -0.3(12) . . . 2 ? N2 C2 N1 C3 -0.4(8) . . . . ? C1 C2 N1 C3 -178.3(8) . . . . ? N2 C2 N1 Zn1 179.6(5) . . . 2 ? C1 C2 N1 Zn1 1.7(11) . . . 2 ? N1 C2 N2 C4 0.2(9) . . . . ? C1 C2 N2 C4 178.1(8) . . . . ? N1 C2 N2 C9 178.8(7) . . . . ? C1 C2 N2 C9 -3.3(13) . . . . ? C3 C4 N2 C2 0.1(9) . . . . ? C8 C4 N2 C2 -175.5(9) . . . . ? C3 C4 N2 C9 -178.5(7) . . . . ? C8 C4 N2 C9 5.9(14) . . . . ? C10 C9 N2 C2 -89.2(10) . . . . ? C10 C9 N2 C4 89.2(10) . . . . ? N4 C14 N3 C15 0.5(10) . . . . ? C13 C14 N3 C15 -178.0(9) . . . . ? N4 C14 N3 C12 -171.7(8) . . . . ? C13 C14 N3 C12 9.8(14) . . . . ? C16 C15 N3 C14 175.6(9) . . . . ? C20 C15 N3 C14 -0.2(9) . . . . ? C16 C15 N3 C12 -12.1(14) . . . . ? C20 C15 N3 C12 172.1(7) . . . . ? C11 C12 N3 C14 85.4(12) . . . . ? C11 C12 N3 C15 -85.3(11) . . . . ? N3 C14 N4 C20 -0.6(10) . . . . ? C13 C14 N4 C20 177.8(10) . . . . ? N3 C14 N4 Zn1 167.7(5) . . . . ? C13 C14 N4 Zn1 -13.9(14) . . . . ? C19 C20 N4 C14 -176.0(9) . . . . ? C15 C20 N4 C14 0.4(9) . . . . ? C19 C20 N4 Zn1 14.5(11) . . . . ? C15 C20 N4 Zn1 -169.0(5) . . . . ? O2 Zn1 N4 C14 173.9(7) . . . . ? N1 Zn1 N4 C14 -95.3(8) 2_554 . . . ? O3 Zn1 N4 C14 24.0(8) 3_457 . . . ? O4 Zn1 N4 C14 26.2(11) 3_457 . . . ? O2 Zn1 N4 C20 -19.6(6) . . . . ? N1 Zn1 N4 C20 71.2(6) 2_554 . . . ? O3 Zn1 N4 C20 -169.5(6) 3_457 . . . ? O4 Zn1 N4 C20 -167.3(6) 3_457 . . . ? O1 C21 O2 Zn1 3.3(9) . . . . ? C22 C21 O2 Zn1 174.4(5) . . . . ? N1 Zn1 O2 C21 -178.8(6) 2_554 . . . ? O3 Zn1 O2 C21 49.2(8) 3_457 . . . ? N4 Zn1 O2 C21 -77.3(6) . . . . ? O4 Zn1 O2 C21 86.3(6) 3_457 . . . ? O4 C28 O3 Zn1 8.4(9) . . . 3_557 ? C27 C28 O3 Zn1 -169.6(6) . . . 3_557 ? O3 C28 O4 Zn1 -7.7(9) . . . 3_557 ? C27 C28 O4 Zn1 170.1(7) . . . 3_557 ? _diffrn_measured_fraction_theta_max 0.895 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.774 _refine_diff_density_min -0.562 _refine_diff_density_rms 0.134 #==== data_7 _database_code_depnum_ccdc_archive 'CCDC 806439' #TrackingRef '- crystals.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 N2 O5 Zn' _chemical_formula_weight 406.71 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 ' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7123(5) _cell_length_b 9.9185(5) _cell_length_c 11.6794(9) _cell_angle_alpha 69.257(6) _cell_angle_beta 70.439(6) _cell_angle_gamma 65.820(6) _cell_volume 839.46(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3816 _cell_measurement_theta_min 4.1 _cell_measurement_theta_max 29.2 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.609 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 418 _exptl_absorpt_coefficient_mu 1.496 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.59 _exptl_absorpt_correction_T_max 0.70 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6019 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0869 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_max 29.21 _reflns_number_total 3802 _reflns_number_gt 2759 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. H atoms of water molecule were refined isotropically with distance restraints of O---H = 0.85+-0.01 \%A. The distance of H1A...H1B was restrained to 1.44+-0.02 \%A. ; _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^)+(0.1049P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.088(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3802 _refine_ls_number_parameters 243 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0807 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1655 _refine_ls_wR_factor_gt 0.1553 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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 0.64925(6) 0.09038(5) 0.55118(5) 0.0228(2) Uani 1 1 d . . . C1 C 0.8077(11) -0.6729(8) 0.3873(8) 0.0638(19) Uani 1 1 d . . . C2 C 0.8739(9) -0.5477(7) 0.3651(6) 0.0538(15) Uani 1 1 d . . . C3 C 1.0314(11) -0.5487(9) 0.2849(7) 0.0694(19) Uani 1 1 d . . . H3 H 1.0908 -0.6253 0.2424 0.083 Uiso 1 1 calc R . . C4 C 1.1035(11) -0.4412(8) 0.2654(8) 0.071(2) Uani 1 1 d . . . H4 H 1.2124 -0.4468 0.2136 0.085 Uiso 1 1 calc R . . C5 C 1.0108(10) -0.3233(8) 0.3247(7) 0.0649(18) Uani 1 1 d . . . H5 H 1.0571 -0.2480 0.3108 0.078 Uiso 1 1 calc R . . C6 C 0.8488(8) -0.3162(7) 0.4050(6) 0.0499(14) Uani 1 1 d . . . C7 C 0.7862(9) -0.4314(7) 0.4240(6) 0.0511(14) Uani 1 1 d . . . H7 H 0.6802 -0.4300 0.4791 0.061 Uiso 1 1 calc R . . C8 C 0.7495(9) -0.1912(7) 0.4690(6) 0.0510(15) Uani 1 1 d . . . C9 C 0.4768(10) 0.3337(8) 0.7645(8) 0.0676(19) Uani 1 1 d . . . H9 H 0.5519 0.3546 0.6875 0.081 Uiso 1 1 calc R . . C10 C 0.4344(8) 0.2029(7) 0.8074(7) 0.0557(16) Uani 1 1 d . . . C11 C 0.2461(13) 0.2714(12) 0.9974(9) 0.089(3) Uani 1 1 d . . . H11 H 0.1688 0.2521 1.0735 0.107 Uiso 1 1 calc R . . C12 C 0.4116(9) -0.0199(8) 0.8306(7) 0.0586(17) Uani 1 1 d . . . C13 C 0.3239(9) 0.1689(8) 0.9222(7) 0.0603(17) Uani 1 1 d . . . C14 C 0.2140(10) -0.0498(10) 1.0471(7) 0.074(2) Uani 1 1 d . . . H14A H 0.2311 -0.0410 1.1217 0.088 Uiso 1 1 calc R . . H14B H 0.2563 -0.1573 1.0490 0.088 Uiso 1 1 calc R . . C15 C 0.4343(11) -0.1625(9) 0.8107(8) 0.073(2) Uani 1 1 d . . . H15A H 0.5275 -0.1823 0.7395 0.109 Uiso 1 1 calc R . . H15B H 0.3300 -0.1570 0.7953 0.109 Uiso 1 1 calc R . . H15C H 0.4604 -0.2434 0.8839 0.109 Uiso 1 1 calc R . . C16 C 0.2891(15) 0.4039(10) 0.9537(10) 0.090(3) Uani 1 1 d . . . H16 H 0.2402 0.4749 1.0016 0.108 Uiso 1 1 calc R . . C17 C 0.4030(12) 0.4320(10) 0.8405(10) 0.082(2) Uani 1 1 d . . . H17 H 0.4307 0.5209 0.8149 0.099 Uiso 1 1 calc R . . C18 C 0.0234(11) 0.0150(11) 1.0482(8) 0.081(2) Uani 1 1 d . . . H18A H -0.0389 -0.0272 1.1302 0.098 Uiso 1 1 calc R . . H18B H -0.0145 0.1247 1.0366 0.098 Uiso 1 1 calc R . . N1 N 0.4876(7) 0.0806(7) 0.7514(5) 0.0604(14) Uani 1 1 d . . . N2 N 0.3124(8) 0.0301(7) 0.9356(6) 0.0658(15) Uani 1 1 d . . . O1 O 0.8759(8) -0.7633(6) 0.3180(7) 0.0891(18) Uani 1 1 d . . . O2 O 0.6786(8) -0.6819(6) 0.4813(6) 0.0870(18) Uani 1 1 d . . . O3 O 0.5936(6) -0.1729(5) 0.5272(5) 0.0643(12) Uani 1 1 d . . . O4 O 0.8215(6) -0.1012(5) 0.4639(5) 0.0724(14) Uani 1 1 d . . . O1W O 0.8793(7) 0.0293(6) 0.6454(6) 0.0691(13) Uani 1 1 d D . . H1A H 0.946(8) -0.060(5) 0.635(10) 0.104 Uiso 1 1 d D . . H1B H 0.939(8) 0.087(7) 0.632(9) 0.104 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0190(3) 0.0207(3) 0.0307(3) -0.0132(2) 0.00153(19) -0.00851(19) C1 0.072(5) 0.048(4) 0.080(5) -0.017(4) -0.026(4) -0.021(3) C2 0.057(4) 0.048(3) 0.057(4) -0.013(3) -0.015(3) -0.017(3) C3 0.076(5) 0.070(4) 0.069(5) -0.029(4) -0.002(4) -0.031(4) C4 0.069(5) 0.074(5) 0.078(5) -0.037(4) 0.010(4) -0.037(4) C5 0.070(5) 0.059(4) 0.070(5) -0.019(3) -0.005(4) -0.032(4) C6 0.051(4) 0.051(3) 0.055(4) -0.014(3) -0.014(3) -0.020(3) C7 0.056(4) 0.047(3) 0.055(4) -0.014(3) -0.014(3) -0.018(3) C8 0.056(4) 0.042(3) 0.060(4) -0.010(3) -0.019(3) -0.019(3) C9 0.068(5) 0.062(4) 0.083(5) -0.026(4) -0.023(4) -0.020(4) C10 0.049(4) 0.062(4) 0.058(4) -0.021(3) -0.015(3) -0.013(3) C11 0.090(6) 0.121(8) 0.072(5) -0.054(5) -0.012(5) -0.028(6) C12 0.049(4) 0.070(4) 0.054(4) -0.012(3) -0.008(3) -0.023(3) C13 0.055(4) 0.072(4) 0.059(4) -0.024(3) -0.013(3) -0.020(3) C14 0.062(5) 0.105(6) 0.053(4) -0.009(4) -0.008(4) -0.040(4) C15 0.070(5) 0.064(4) 0.082(5) -0.017(4) -0.011(4) -0.026(4) C16 0.111(8) 0.079(6) 0.091(7) -0.043(5) -0.025(6) -0.020(5) C17 0.087(6) 0.073(5) 0.097(7) -0.031(5) -0.029(6) -0.021(4) C18 0.073(5) 0.106(6) 0.061(5) -0.011(4) -0.013(4) -0.036(5) N1 0.055(3) 0.072(4) 0.059(3) -0.018(3) -0.010(3) -0.026(3) N2 0.063(4) 0.079(4) 0.056(4) -0.019(3) -0.009(3) -0.026(3) O1 0.099(4) 0.062(3) 0.126(5) -0.043(3) -0.040(4) -0.018(3) O2 0.086(4) 0.066(3) 0.109(5) -0.012(3) -0.012(4) -0.041(3) O3 0.048(3) 0.070(3) 0.071(3) -0.025(2) -0.008(2) -0.015(2) O4 0.068(3) 0.059(3) 0.099(4) -0.038(3) -0.012(3) -0.019(2) O1W 0.062(3) 0.069(3) 0.083(4) -0.027(3) -0.020(3) -0.019(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 2.205(5) 1_565 ? Zn1 O4 2.216(5) . ? Zn1 N1 2.281(6) . ? Zn1 O3 2.309(5) 2_656 ? Zn1 O1W 2.368(5) . ? C1 O1 1.252(10) . ? C1 O2 1.290(10) . ? C1 C2 1.483(9) . ? C2 C7 1.370(9) . ? C2 C3 1.376(10) . ? C3 C4 1.366(10) . ? C3 H3 0.9300 . ? C4 C5 1.386(11) . ? C4 H4 0.9300 . ? C5 C6 1.399(10) . ? C5 H5 0.9300 . ? C6 C7 1.378(8) . ? C6 C8 1.480(9) . ? C7 H7 0.9300 . ? C8 O4 1.261(7) . ? C8 O3 1.268(8) . ? C9 C17 1.368(12) . ? C9 C10 1.370(10) . ? C9 H9 0.9300 . ? C10 C13 1.385(10) . ? C10 N1 1.420(9) . ? C11 C16 1.389(13) . ? C11 C13 1.390(11) . ? C11 H11 0.9300 . ? C12 N1 1.329(9) . ? C12 N2 1.366(10) . ? C12 C15 1.438(11) . ? C13 N2 1.371(9) . ? C14 N2 1.462(10) . ? C14 C18 1.512(11) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.377(14) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C18 1.472(17) 2_557 ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? O2 Zn1 2.205(5) 1_545 ? O3 Zn1 2.309(5) 2_656 ? O1W H1A 0.862(10) . ? O1W H1B 0.863(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Zn1 O4 122.8(2) 1_565 . ? O2 Zn1 N1 105.2(2) 1_565 . ? O4 Zn1 N1 128.7(2) . . ? O2 Zn1 O3 93.2(2) 1_565 2_656 ? O4 Zn1 O3 102.01(18) . 2_656 ? N1 Zn1 O3 91.55(19) . 2_656 ? O2 Zn1 O1W 83.0(2) 1_565 . ? O4 Zn1 O1W 85.08(19) . . ? N1 Zn1 O1W 83.7(2) . . ? O3 Zn1 O1W 172.91(18) 2_656 . ? O1 C1 O2 123.2(7) . . ? O1 C1 C2 120.9(8) . . ? O2 C1 C2 115.9(7) . . ? C7 C2 C3 117.9(6) . . ? C7 C2 C1 122.5(7) . . ? C3 C2 C1 119.5(7) . . ? C4 C3 C2 122.4(8) . . ? C4 C3 H3 118.8 . . ? C2 C3 H3 118.8 . . ? C3 C4 C5 118.5(7) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C4 C5 C6 121.0(6) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C7 C6 C5 117.6(6) . . ? C7 C6 C8 121.2(6) . . ? C5 C6 C8 121.2(6) . . ? C2 C7 C6 122.6(7) . . ? C2 C7 H7 118.7 . . ? C6 C7 H7 118.7 . . ? O4 C8 O3 120.0(6) . . ? O4 C8 C6 119.1(6) . . ? O3 C8 C6 120.9(5) . . ? C17 C9 C10 116.6(8) . . ? C17 C9 H9 121.7 . . ? C10 C9 H9 121.7 . . ? C9 C10 C13 122.7(7) . . ? C9 C10 N1 130.2(7) . . ? C13 C10 N1 107.1(6) . . ? C16 C11 C13 117.0(9) . . ? C16 C11 H11 121.5 . . ? C13 C11 H11 121.5 . . ? N1 C12 N2 110.0(6) . . ? N1 C12 C15 125.0(7) . . ? N2 C12 C15 124.9(7) . . ? N2 C13 C10 107.1(7) . . ? N2 C13 C11 132.6(8) . . ? C10 C13 C11 120.3(8) . . ? N2 C14 C18 111.5(6) . . ? N2 C14 H14A 109.3 . . ? C18 C14 H14A 109.3 . . ? N2 C14 H14B 109.3 . . ? C18 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C11 121.1(9) . . ? C17 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? C9 C17 C16 122.3(9) . . ? C9 C17 H17 118.8 . . ? C16 C17 H17 118.8 . . ? C18 C18 C14 114.8(10) 2_557 . ? C18 C18 H18A 108.6 2_557 . ? C14 C18 H18A 108.6 . . ? C18 C18 H18B 108.6 2_557 . ? C14 C18 H18B 108.6 . . ? H18A C18 H18B 107.6 . . ? C12 N1 C10 107.2(6) . . ? C12 N1 Zn1 130.9(5) . . ? C10 N1 Zn1 121.5(4) . . ? C12 N2 C13 108.5(6) . . ? C12 N2 C14 127.2(7) . . ? C13 N2 C14 124.3(7) . . ? C1 O2 Zn1 113.4(5) . 1_545 ? C8 O3 Zn1 129.5(4) . 2_656 ? C8 O4 Zn1 114.5(5) . . ? Zn1 O1W H1A 104(6) . . ? Zn1 O1W H1B 126(6) . . ? H1A O1W H1B 111(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C7 168.4(6) . . . . ? O2 C1 C2 C7 -11.9(10) . . . . ? O1 C1 C2 C3 -13.2(10) . . . . ? O2 C1 C2 C3 166.5(7) . . . . ? C7 C2 C3 C4 1.9(11) . . . . ? C1 C2 C3 C4 -176.6(7) . . . . ? C2 C3 C4 C5 -2.9(12) . . . . ? C3 C4 C5 C6 1.5(12) . . . . ? C4 C5 C6 C7 0.8(10) . . . . ? C4 C5 C6 C8 179.7(7) . . . . ? C3 C2 C7 C6 0.6(10) . . . . ? C1 C2 C7 C6 179.0(6) . . . . ? C5 C6 C7 C2 -1.9(9) . . . . ? C8 C6 C7 C2 179.2(6) . . . . ? C7 C6 C8 O4 169.6(6) . . . . ? C5 C6 C8 O4 -9.2(9) . . . . ? C7 C6 C8 O3 -11.2(9) . . . . ? C5 C6 C8 O3 169.9(6) . . . . ? C17 C9 C10 C13 -0.5(10) . . . . ? C17 C9 C10 N1 179.6(7) . . . . ? C9 C10 C13 N2 -179.2(6) . . . . ? N1 C10 C13 N2 0.7(7) . . . . ? C9 C10 C13 C11 2.2(10) . . . . ? N1 C10 C13 C11 -177.9(6) . . . . ? C16 C11 C13 N2 179.8(8) . . . . ? C16 C11 C13 C10 -2.1(11) . . . . ? C13 C11 C16 C17 0.4(13) . . . . ? C10 C9 C17 C16 -1.2(12) . . . . ? C11 C16 C17 C9 1.3(14) . . . . ? N2 C14 C18 C18 69.1(12) . . . 2_557 ? N2 C12 N1 C10 -0.3(7) . . . . ? C15 C12 N1 C10 -178.6(6) . . . . ? N2 C12 N1 Zn1 -173.3(4) . . . . ? C15 C12 N1 Zn1 8.4(10) . . . . ? C9 C10 N1 C12 179.6(7) . . . . ? C13 C10 N1 C12 -0.2(7) . . . . ? C9 C10 N1 Zn1 -6.6(9) . . . . ? C13 C10 N1 Zn1 173.5(4) . . . . ? O2 Zn1 N1 C12 169.5(6) 1_565 . . . ? O4 Zn1 N1 C12 -31.0(7) . . . . ? O3 Zn1 N1 C12 75.7(6) 2_656 . . . ? O1W Zn1 N1 C12 -109.6(6) . . . . ? O2 Zn1 N1 C10 -2.7(5) 1_565 . . . ? O4 Zn1 N1 C10 156.8(4) . . . . ? O3 Zn1 N1 C10 -96.4(5) 2_656 . . . ? O1W Zn1 N1 C10 78.3(5) . . . . ? N1 C12 N2 C13 0.7(7) . . . . ? C15 C12 N2 C13 179.0(7) . . . . ? N1 C12 N2 C14 -177.2(6) . . . . ? C15 C12 N2 C14 1.1(11) . . . . ? C10 C13 N2 C12 -0.9(7) . . . . ? C11 C13 N2 C12 177.5(8) . . . . ? C10 C13 N2 C14 177.1(6) . . . . ? C11 C13 N2 C14 -4.5(12) . . . . ? C18 C14 N2 C12 -102.9(9) . . . . ? C18 C14 N2 C13 79.4(9) . . . . ? O1 C1 O2 Zn1 21.0(9) . . . 1_545 ? C2 C1 O2 Zn1 -158.6(4) . . . 1_545 ? O4 C8 O3 Zn1 109.0(6) . . . 2_656 ? C6 C8 O3 Zn1 -70.2(7) . . . 2_656 ? O3 C8 O4 Zn1 -3.9(8) . . . . ? C6 C8 O4 Zn1 175.3(4) . . . . ? O2 Zn1 O4 C8 -147.5(4) 1_565 . . . ? N1 Zn1 O4 C8 56.2(5) . . . . ? O3 Zn1 O4 C8 -45.6(5) 2_656 . . . ? O1W Zn1 O4 C8 134.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.839 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.820 _refine_diff_density_min -0.665 _refine_diff_density_rms 0.149 #==== data_8 _database_code_depnum_ccdc_archive 'CCDC 806440' #TrackingRef '- crystals.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H15 N2 O5 Zn' _chemical_formula_weight 356.65 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.8685(3) _cell_length_b 16.3185(4) _cell_length_c 8.5098(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.088(2) _cell_angle_gamma 90.00 _cell_volume 1509.28(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3244 _cell_measurement_theta_min 4.2 _cell_measurement_theta_max 29.2 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.570 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 732 _exptl_absorpt_coefficient_mu 1.652 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.56 _exptl_absorpt_correction_T_max 0.59 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5345 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0540 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 4.19 _diffrn_reflns_theta_max 29.20 _reflns_number_total 3243 _reflns_number_gt 2269 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. H atoms of water molecule were refined isotropically with distance restraints of O---H = 0.87+-0.02 \%A. The distances of H1e...H1f and Zn1...H1f were restrained to 1.40+-0.02 and 2.78+-0.02 \%A, respectively. ; _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^)+(0.1397P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3243 _refine_ls_number_parameters 206 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0843 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1971 _refine_ls_wR_factor_gt 0.1823 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.010 _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 0.40139(4) 0.09471(3) 0.52375(6) 0.0224(2) Uani 1 1 d D . . C1 C 0.2518(8) -0.0562(5) 0.2771(11) 0.074(2) Uani 1 1 d . . . H1A H 0.2815 -0.0445 0.1733 0.110 Uiso 1 1 calc R . . H1B H 0.2044 -0.1058 0.2752 0.110 Uiso 1 1 calc R . . H1C H 0.3204 -0.0627 0.3473 0.110 Uiso 1 1 calc R . . C2 C 0.1755(6) 0.0106(4) 0.3306(8) 0.0529(16) Uani 1 1 d . . . C3 C 0.1150(6) 0.1295(5) 0.4301(9) 0.0545(17) Uani 1 1 d . . . C4 C 0.0124(7) 0.0933(5) 0.3619(8) 0.0563(18) Uani 1 1 d . . . C5 C -0.1020(7) 0.1273(7) 0.3660(11) 0.076(2) Uani 1 1 d . . . H5 H -0.1702 0.1023 0.3204 0.092 Uiso 1 1 calc R . . C6 C -0.1096(9) 0.2039(7) 0.4451(12) 0.087(3) Uani 1 1 d . . . H6 H -0.1857 0.2296 0.4537 0.105 Uiso 1 1 calc R . . C7 C -0.0084(9) 0.2409(7) 0.5090(11) 0.087(3) Uani 1 1 d . . . H7 H -0.0166 0.2921 0.5557 0.104 Uiso 1 1 calc R . . C8 C 0.1049(8) 0.2042(6) 0.5057(10) 0.074(2) Uani 1 1 d . . . H8 H 0.1729 0.2287 0.5527 0.089 Uiso 1 1 calc R . . C9 C -0.0243(7) -0.0390(6) 0.2155(9) 0.068(2) Uani 1 1 d . . . H9A H -0.1006 -0.0463 0.2729 0.082 Uiso 1 1 calc R . . H9B H 0.0164 -0.0918 0.2090 0.082 Uiso 1 1 calc R . . C10 C -0.0531(10) -0.0075(8) 0.0476(10) 0.098(4) Uani 1 1 d . . . H10A H -0.1047 -0.0475 -0.0051 0.118 Uiso 1 1 calc R . . H10B H -0.0998 0.0429 0.0560 0.118 Uiso 1 1 calc R . . C11 C 0.4316(7) -0.0489(4) 0.7837(8) 0.0529(16) Uani 1 1 d . . . C12 C 0.4965(10) -0.1238(6) 0.8474(12) 0.090(3) Uani 1 1 d . . . H12 H 0.5759 -0.1377 0.8165 0.107 Uiso 1 1 calc R . . C13 C 0.4312(9) -0.1705(6) 0.9543(15) 0.112(4) Uani 1 1 d . . . H13 H 0.3583 -0.1539 1.0017 0.134 Uiso 1 1 calc R . . C14 C 0.4941(8) -0.2532(5) 0.9849(11) 0.069(2) Uani 1 1 d . . . N1 N 0.0540(5) 0.0183(4) 0.2992(7) 0.0578(15) Uani 1 1 d . . . N2 N 0.2163(5) 0.0769(4) 0.4113(7) 0.0573(15) Uani 1 1 d . . . O1 O 0.4667(5) -0.0216(3) 0.6515(6) 0.0625(13) Uani 1 1 d . . . O2 O 0.3502(6) -0.0167(4) 0.8637(8) 0.092(2) Uani 1 1 d . . . O3 O 0.5979(6) -0.2577(4) 1.0529(8) 0.0786(16) Uani 1 1 d . . . O4 O 0.4414(6) -0.3171(4) 0.9316(9) 0.0886(19) Uani 1 1 d . . . O1W O 0.3091(6) 0.1349(4) 0.7583(7) 0.0733(15) Uani 1 1 d D . . H1F H 0.330(8) 0.098(3) 0.835(3) 0.110 Uiso 1 1 d D . . H1E H 0.333(9) 0.181(3) 0.811(9) 0.110 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0245(3) 0.0166(3) 0.0260(3) -0.0011(2) -0.0054(2) 0.0008(2) C1 0.075(5) 0.061(5) 0.085(6) -0.015(5) -0.017(4) 0.018(4) C2 0.055(4) 0.055(4) 0.049(4) -0.001(3) -0.007(3) -0.001(3) C3 0.056(4) 0.054(4) 0.053(4) 0.000(3) 0.005(3) 0.003(3) C4 0.052(4) 0.071(5) 0.046(4) 0.009(3) -0.001(3) 0.003(3) C5 0.050(4) 0.101(7) 0.078(5) 0.021(5) 0.004(4) 0.008(5) C6 0.076(6) 0.091(7) 0.094(7) 0.000(6) 0.004(5) 0.027(6) C7 0.076(6) 0.087(7) 0.097(7) -0.013(6) 0.007(5) 0.018(5) C8 0.085(6) 0.059(5) 0.077(5) -0.010(4) 0.000(4) 0.010(4) C9 0.067(5) 0.081(6) 0.057(4) 0.000(4) -0.004(3) -0.023(4) C10 0.100(6) 0.133(10) 0.061(5) -0.004(5) -0.010(4) -0.055(7) C11 0.060(4) 0.049(4) 0.050(4) 0.002(3) 0.005(3) 0.002(3) C12 0.095(6) 0.084(6) 0.090(6) 0.031(5) 0.034(5) 0.037(5) C13 0.093(7) 0.057(5) 0.186(11) 0.053(7) 0.069(8) 0.023(5) C14 0.065(5) 0.050(4) 0.093(6) 0.014(4) 0.017(4) 0.013(4) N1 0.054(3) 0.073(4) 0.047(3) -0.001(3) -0.002(3) -0.006(3) N2 0.053(3) 0.065(4) 0.054(3) -0.004(3) -0.007(3) 0.001(3) O1 0.074(3) 0.053(3) 0.060(3) 0.007(2) 0.006(2) 0.005(3) O2 0.096(4) 0.079(4) 0.102(5) 0.025(4) 0.043(4) 0.029(4) O3 0.080(4) 0.054(3) 0.102(5) -0.005(3) -0.001(3) 0.006(3) O4 0.081(4) 0.053(3) 0.132(6) -0.004(4) -0.010(4) -0.003(3) O1W 0.087(4) 0.060(3) 0.073(4) 0.003(3) -0.003(3) 0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N2 2.246(6) . ? Zn1 O4 2.266(6) 2_656 ? Zn1 O1 2.299(5) . ? Zn1 O1W 2.329(6) . ? Zn1 O1 2.389(5) 3_656 ? C1 C2 1.444(10) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N1 1.352(9) . ? C2 N2 1.355(9) . ? C3 C8 1.382(12) . ? C3 C4 1.389(11) . ? C3 N2 1.406(9) . ? C4 C5 1.363(11) . ? C4 N1 1.410(10) . ? C5 C6 1.422(14) . ? C5 H5 0.9300 . ? C6 C7 1.367(14) . ? C6 H6 0.9300 . ? C7 C8 1.370(12) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 N1 1.451(9) . ? C9 C10 1.549(12) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C10 1.433(18) 3 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O2 1.234(9) . ? C11 O1 1.270(8) . ? C11 C12 1.511(11) . ? C12 C13 1.384(12) . ? C12 H12 0.9300 . ? C13 C14 1.535(11) . ? C13 H13 0.9300 . ? C14 O3 1.269(10) . ? C14 O4 1.273(11) . ? O1 Zn1 2.389(5) 3_656 ? O4 Zn1 2.266(6) 2_646 ? O1W H1F 0.92(2) . ? O1W H1E 0.92(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Zn1 O4 146.0(2) . 2_656 ? N2 Zn1 O1 111.7(2) . . ? O4 Zn1 O1 102.3(2) 2_656 . ? N2 Zn1 O1W 90.9(2) . . ? O4 Zn1 O1W 90.2(2) 2_656 . ? O1 Zn1 O1W 87.73(19) . . ? N2 Zn1 O1 102.0(2) . 3_656 ? O4 Zn1 O1 88.2(2) 2_656 3_656 ? O1 Zn1 O1 72.40(19) . 3_656 ? O1W Zn1 O1 159.2(2) . 3_656 ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 N2 110.2(6) . . ? N1 C2 C1 124.7(7) . . ? N2 C2 C1 125.0(7) . . ? C8 C3 C4 120.4(7) . . ? C8 C3 N2 130.9(7) . . ? C4 C3 N2 108.7(7) . . ? C5 C4 C3 123.2(8) . . ? C5 C4 N1 131.1(8) . . ? C3 C4 N1 105.7(6) . . ? C4 C5 C6 115.1(9) . . ? C4 C5 H5 122.5 . . ? C6 C5 H5 122.5 . . ? C7 C6 C5 122.0(9) . . ? C7 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? C6 C7 C8 121.4(10) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C7 C8 C3 117.8(9) . . ? C7 C8 H8 121.1 . . ? C3 C8 H8 121.1 . . ? N1 C9 C10 110.9(7) . . ? N1 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C10 C10 C9 114.6(12) 3 . ? C10 C10 H10A 108.6 3 . ? C9 C10 H10A 108.6 . . ? C10 C10 H10B 108.6 3 . ? C9 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? O2 C11 O1 123.8(7) . . ? O2 C11 C12 118.8(6) . . ? O1 C11 C12 117.4(6) . . ? C13 C12 C11 116.2(8) . . ? C13 C12 H12 121.9 . . ? C11 C12 H12 121.9 . . ? C12 C13 C14 111.5(7) . . ? C12 C13 H13 124.2 . . ? C14 C13 H13 124.2 . . ? O3 C14 O4 121.0(8) . . ? O3 C14 C13 121.5(9) . . ? O4 C14 C13 117.4(9) . . ? C2 N1 C4 108.6(6) . . ? C2 N1 C9 127.6(7) . . ? C4 N1 C9 123.8(6) . . ? C2 N2 C3 106.8(6) . . ? C2 N2 Zn1 127.7(5) . . ? C3 N2 Zn1 125.0(5) . . ? C11 O1 Zn1 128.0(4) . . ? C11 O1 Zn1 124.0(5) . 3_656 ? Zn1 O1 Zn1 107.60(19) . 3_656 ? C14 O4 Zn1 97.0(5) . 2_646 ? Zn1 O1W H1F 109(4) . . ? Zn1 O1W H1E 122(6) . . ? H1F O1W H1E 97(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 C3 C4 C5 -0.6(12) . . . . ? N2 C3 C4 C5 177.1(7) . . . . ? C8 C3 C4 N1 -178.8(7) . . . . ? N2 C3 C4 N1 -1.0(8) . . . . ? C3 C4 C5 C6 0.4(12) . . . . ? N1 C4 C5 C6 177.9(8) . . . . ? C4 C5 C6 C7 1.4(14) . . . . ? C5 C6 C7 C8 -2.8(15) . . . . ? C6 C7 C8 C3 2.4(14) . . . . ? C4 C3 C8 C7 -0.7(12) . . . . ? N2 C3 C8 C7 -178.0(8) . . . . ? N1 C9 C10 C10 57.7(16) . . . 3 ? O2 C11 C12 C13 25.6(15) . . . . ? O1 C11 C12 C13 -156.1(10) . . . . ? C11 C12 C13 C14 168.3(10) . . . . ? C12 C13 C14 O3 66.4(14) . . . . ? C12 C13 C14 O4 -109.8(11) . . . . ? N2 C2 N1 C4 0.1(8) . . . . ? C1 C2 N1 C4 -176.4(7) . . . . ? N2 C2 N1 C9 -180.0(6) . . . . ? C1 C2 N1 C9 3.5(12) . . . . ? C5 C4 N1 C2 -177.4(8) . . . . ? C3 C4 N1 C2 0.5(8) . . . . ? C5 C4 N1 C9 2.7(12) . . . . ? C3 C4 N1 C9 -179.4(6) . . . . ? C10 C9 N1 C2 -105.0(10) . . . . ? C10 C9 N1 C4 74.9(9) . . . . ? N1 C2 N2 C3 -0.7(8) . . . . ? C1 C2 N2 C3 175.8(7) . . . . ? N1 C2 N2 Zn1 171.8(5) . . . . ? C1 C2 N2 Zn1 -11.7(11) . . . . ? C8 C3 N2 C2 178.5(8) . . . . ? C4 C3 N2 C2 1.1(8) . . . . ? C8 C3 N2 Zn1 5.7(12) . . . . ? C4 C3 N2 Zn1 -171.7(5) . . . . ? O4 Zn1 N2 C2 138.4(6) 2_656 . . . ? O1 Zn1 N2 C2 -42.2(6) . . . . ? O1W Zn1 N2 C2 -130.1(6) . . . . ? O1 Zn1 N2 C2 33.5(6) 3_656 . . . ? O4 Zn1 N2 C3 -50.4(8) 2_656 . . . ? O1 Zn1 N2 C3 129.1(6) . . . . ? O1W Zn1 N2 C3 41.2(6) . . . . ? O1 Zn1 N2 C3 -155.3(6) 3_656 . . . ? O2 C11 O1 Zn1 2.8(11) . . . . ? C12 C11 O1 Zn1 -175.4(7) . . . . ? O2 C11 O1 Zn1 -169.2(6) . . . 3_656 ? C12 C11 O1 Zn1 12.6(10) . . . 3_656 ? N2 Zn1 O1 C11 -76.9(6) . . . . ? O4 Zn1 O1 C11 102.8(6) 2_656 . . . ? O1W Zn1 O1 C11 13.2(6) . . . . ? O1 Zn1 O1 C11 -173.1(7) 3_656 . . . ? N2 Zn1 O1 Zn1 96.2(2) . . . 3_656 ? O4 Zn1 O1 Zn1 -84.1(3) 2_656 . . 3_656 ? O1W Zn1 O1 Zn1 -173.8(2) . . . 3_656 ? O1 Zn1 O1 Zn1 0.0 3_656 . . 3_656 ? O3 C14 O4 Zn1 -6.8(9) . . . 2_646 ? C13 C14 O4 Zn1 169.5(6) . . . 2_646 ? 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 H1F O2 0.92(2) 1.90(5) 2.669(8) 140(6) . O1W H1E O3 0.92(2) 1.86(3) 2.759(9) 166(8) 3_657 _diffrn_measured_fraction_theta_max 0.794 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 1.434 _refine_diff_density_min -0.826 _refine_diff_density_rms 0.160 #==== data_9 _database_code_depnum_ccdc_archive 'CCDC 806441' #TrackingRef '- crystals.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 Ag2 N4 O5' _chemical_formula_weight 716.28 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' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_space_group_name_Hall '-P 2yn ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.3571(2) _cell_length_b 16.6387(4) _cell_length_c 15.4241(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.106(2) _cell_angle_gamma 90.00 _cell_volume 2631.46(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6162 _cell_measurement_theta_min 4.2 _cell_measurement_theta_max 29.2 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.808 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1432 _exptl_absorpt_coefficient_mu 1.535 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.60 _exptl_absorpt_correction_T_max 0.66 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12506 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.16 _diffrn_reflns_theta_max 29.20 _reflns_number_total 6162 _reflns_number_gt 3587 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. H atoms of water molecule were refined isotropically with distance restraints of O---H = 0.89+-0.02 \%A. The distance of H1E...H1F was restrained to 1.44+-0.02 \%A. ; _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^)+(0.0312P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6162 _refine_ls_number_parameters 360 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0711 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0676 _refine_ls_wR_factor_gt 0.0620 _refine_ls_goodness_of_fit_ref 0.823 _refine_ls_restrained_S_all 0.823 _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 Ag1 Ag 0.32219(2) 0.083160(16) 0.116788(16) 0.04295(8) Uani 1 1 d . . . Ag2 Ag 0.31170(2) -0.089936(17) 0.131362(18) 0.05180(9) Uani 1 1 d . . . C1 C 0.0282(3) -0.1981(2) 0.0928(2) 0.0449(8) Uani 1 1 d . . . H1A H 0.0776 -0.1647 0.0587 0.067 Uiso 1 1 calc R . . H1B H -0.0610 -0.1806 0.0850 0.067 Uiso 1 1 calc R . . H1C H 0.0322 -0.2529 0.0738 0.067 Uiso 1 1 calc R . . C2 C 0.0830(3) -0.19228(18) 0.18576(19) 0.0326(7) Uani 1 1 d . . . C3 C 0.2042(3) -0.15960(17) 0.3062(2) 0.0306(7) Uani 1 1 d . . . C4 C 0.2957(3) -0.1266(2) 0.3707(2) 0.0424(8) Uani 1 1 d . . . H4 H 0.3630 -0.0943 0.3566 0.051 Uiso 1 1 calc R . . C5 C 0.2827(3) -0.1435(3) 0.4563(3) 0.0593(10) Uani 1 1 d . . . H5 H 0.3406 -0.1204 0.5009 0.071 Uiso 1 1 calc R . . C6 C 0.1856(4) -0.1943(3) 0.4779(2) 0.0637(11) Uani 1 1 d . . . H6 H 0.1824 -0.2062 0.5364 0.076 Uiso 1 1 calc R . . C7 C 0.0947(3) -0.2269(2) 0.4151(2) 0.0470(9) Uani 1 1 d . . . H7 H 0.0295 -0.2607 0.4297 0.056 Uiso 1 1 calc R . . C8 C 0.1036(3) -0.20783(18) 0.32945(19) 0.0318(7) Uani 1 1 d . . . C9 C -0.0872(3) -0.28017(18) 0.2411(2) 0.0387(8) Uani 1 1 d . . . H9A H -0.0812 -0.3167 0.2905 0.046 Uiso 1 1 calc R . . H9B H -0.0884 -0.3123 0.1885 0.046 Uiso 1 1 calc R . . C10 C -0.2144(3) -0.23359(17) 0.2354(2) 0.0367(7) Uani 1 1 d . . . H10A H -0.2256 -0.2011 0.1827 0.044 Uiso 1 1 calc R . . H10B H -0.2110 -0.1978 0.2853 0.044 Uiso 1 1 calc R . . C11 C -0.3300(3) -0.29054(18) 0.2339(2) 0.0357(7) Uani 1 1 d . . . H11A H -0.3278 -0.3298 0.1876 0.043 Uiso 1 1 calc R . . H11B H -0.3229 -0.3192 0.2891 0.043 Uiso 1 1 calc R . . C12 C -0.4582(3) -0.24616(18) 0.2191(2) 0.0399(8) Uani 1 1 d . . . H12A H -0.4576 -0.2044 0.2631 0.048 Uiso 1 1 calc R . . H12B H -0.4675 -0.2204 0.1622 0.048 Uiso 1 1 calc R . . C13 C -0.6568(3) -0.32780(17) 0.1529(2) 0.0308(7) Uani 1 1 d . . . C14 C -0.6622(3) -0.3192(2) 0.0633(2) 0.0444(8) Uani 1 1 d . . . H14 H -0.6020 -0.2877 0.0393 0.053 Uiso 1 1 calc R . . C15 C -0.7610(4) -0.3594(2) 0.0112(2) 0.0511(9) Uani 1 1 d . . . H15 H -0.7667 -0.3557 -0.0494 0.061 Uiso 1 1 calc R . . C16 C -0.8517(3) -0.4050(2) 0.0471(2) 0.0496(9) Uani 1 1 d . . . H16 H -0.9166 -0.4315 0.0100 0.059 Uiso 1 1 calc R . . C17 C -0.8488(3) -0.41246(19) 0.1363(2) 0.0391(7) Uani 1 1 d . . . H17 H -0.9112 -0.4425 0.1598 0.047 Uiso 1 1 calc R . . C18 C -0.7493(3) -0.37340(17) 0.18989(19) 0.0293(7) Uani 1 1 d . . . C19 C -0.6114(3) -0.32779(18) 0.2970(2) 0.0337(7) Uani 1 1 d . . . C20 C -0.5429(3) -0.3127(2) 0.3862(2) 0.0479(9) Uani 1 1 d . . . H20A H -0.6017 -0.3218 0.4281 0.072 Uiso 1 1 calc R . . H20B H -0.5129 -0.2580 0.3905 0.072 Uiso 1 1 calc R . . H20C H -0.4697 -0.3483 0.3980 0.072 Uiso 1 1 calc R . . C21 C 0.2284(3) 0.0113(2) -0.0604(2) 0.0363(7) Uani 1 1 d . . . C22 C 0.1887(3) 0.00577(16) -0.1582(2) 0.0302(6) Uani 1 1 d . . . C23 C 0.0555(3) 0.00661(18) -0.1914(2) 0.0399(8) Uani 1 1 d . . . H23 H -0.0061 0.0066 -0.1530 0.048 Uiso 1 1 calc R . . C24 C 0.0151(3) 0.00749(19) -0.2800(3) 0.0490(9) Uani 1 1 d . . . H24 H -0.0737 0.0069 -0.3008 0.059 Uiso 1 1 calc R . . C25 C 0.1024(4) 0.0092(2) -0.3378(3) 0.0537(10) Uani 1 1 d . . . H25 H 0.0736 0.0107 -0.3977 0.064 Uiso 1 1 calc R . . C26 C 0.2357(3) 0.00851(18) -0.3068(2) 0.0422(8) Uani 1 1 d . . . H26 H 0.2959 0.0098 -0.3462 0.051 Uiso 1 1 calc R . . C27 C 0.2784(3) 0.00596(17) -0.21794(19) 0.0310(7) Uani 1 1 d . . . C28 C 0.4228(3) -0.00106(18) -0.1880(2) 0.0318(7) Uani 1 1 d . . . N1 N -0.5711(2) -0.29926(14) 0.22322(16) 0.0312(6) Uani 1 1 d . . . N2 N -0.7182(2) -0.37138(15) 0.28031(16) 0.0338(6) Uani 1 1 d . . . N3 N 0.0287(2) -0.22850(14) 0.25108(16) 0.0308(6) Uani 1 1 d . . . N4 N 0.1891(2) -0.15099(14) 0.21609(16) 0.0309(6) Uani 1 1 d . . . O1 O 0.1961(2) -0.04455(16) -0.01362(16) 0.0599(7) Uani 1 1 d . . . O3 O 0.2886(2) 0.07397(14) -0.03293(14) 0.0453(6) Uani 1 1 d . . . O7 O 0.45777(18) -0.04898(14) -0.12632(14) 0.0404(5) Uani 1 1 d . . . O8 O 0.4985(2) 0.03858(14) -0.22772(15) 0.0486(6) Uani 1 1 d . . . O1W O 0.4576(2) -0.12969(13) 0.03143(16) 0.0443(6) Uani 1 1 d D . . H1E H 0.535(2) -0.115(2) 0.051(2) 0.066 Uiso 1 1 d D . . H1F H 0.429(3) -0.106(2) -0.0176(16) 0.066 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.04135(14) 0.05130(16) 0.03994(15) -0.00673(13) 0.01881(11) 0.00361(13) Ag2 0.04567(15) 0.05943(18) 0.05559(19) 0.00733(14) 0.02553(13) -0.01163(14) C1 0.0442(18) 0.055(2) 0.035(2) 0.0021(16) 0.0042(15) -0.0063(17) C2 0.0298(15) 0.0408(18) 0.0284(17) 0.0037(14) 0.0084(13) 0.0032(14) C3 0.0299(15) 0.0316(16) 0.0313(18) 0.0032(13) 0.0079(13) 0.0026(13) C4 0.0349(17) 0.045(2) 0.046(2) -0.0004(16) -0.0013(15) -0.0017(15) C5 0.052(2) 0.082(3) 0.040(2) -0.005(2) -0.0067(18) -0.004(2) C6 0.068(3) 0.101(3) 0.024(2) 0.013(2) 0.0119(19) 0.015(2) C7 0.0442(19) 0.063(2) 0.037(2) 0.0150(17) 0.0180(16) 0.0061(17) C8 0.0281(15) 0.0384(18) 0.0306(18) 0.0082(14) 0.0102(13) 0.0029(13) C9 0.0310(16) 0.0327(17) 0.053(2) 0.0025(15) 0.0096(14) -0.0082(14) C10 0.0301(15) 0.0294(17) 0.052(2) 0.0025(15) 0.0104(14) -0.0059(14) C11 0.0293(15) 0.0339(18) 0.045(2) 0.0038(14) 0.0098(14) -0.0061(14) C12 0.0303(16) 0.0352(18) 0.054(2) 0.0073(16) 0.0060(14) -0.0064(14) C13 0.0253(15) 0.0329(17) 0.0347(18) 0.0027(13) 0.0065(13) 0.0006(13) C14 0.0449(19) 0.055(2) 0.036(2) 0.0066(16) 0.0159(16) -0.0039(17) C15 0.061(2) 0.062(2) 0.031(2) -0.0002(17) 0.0070(17) 0.001(2) C16 0.0460(19) 0.056(2) 0.044(2) -0.0095(18) -0.0051(16) -0.0023(17) C17 0.0290(15) 0.0395(18) 0.049(2) -0.0003(16) 0.0049(14) -0.0031(15) C18 0.0227(14) 0.0338(16) 0.0326(18) 0.0004(13) 0.0083(13) 0.0027(13) C19 0.0300(16) 0.0410(19) 0.0307(18) 0.0029(14) 0.0064(14) 0.0038(14) C20 0.0420(18) 0.065(2) 0.036(2) -0.0036(17) 0.0050(16) -0.0036(17) C21 0.0245(15) 0.049(2) 0.0373(19) 0.0039(16) 0.0094(13) 0.0085(15) C22 0.0296(14) 0.0223(15) 0.0379(18) 0.0013(13) 0.0021(12) -0.0008(13) C23 0.0279(15) 0.0318(18) 0.059(2) 0.0010(16) 0.0014(14) -0.0032(14) C24 0.0378(18) 0.038(2) 0.066(3) 0.0032(18) -0.0114(18) 0.0048(16) C25 0.064(2) 0.045(2) 0.044(2) 0.0033(17) -0.0214(19) 0.0017(19) C26 0.052(2) 0.0378(19) 0.037(2) 0.0040(15) 0.0058(15) 0.0000(16) C27 0.0365(16) 0.0248(15) 0.0312(18) 0.0017(13) 0.0033(13) -0.0006(13) C28 0.0318(15) 0.0313(16) 0.0336(18) -0.0087(15) 0.0090(13) 0.0027(15) N1 0.0237(12) 0.0363(14) 0.0342(15) 0.0041(12) 0.0063(11) -0.0035(11) N2 0.0273(13) 0.0416(15) 0.0343(16) 0.0063(12) 0.0103(11) 0.0004(12) N3 0.0241(12) 0.0339(14) 0.0358(15) 0.0049(11) 0.0095(11) -0.0036(11) N4 0.0254(12) 0.0384(15) 0.0299(15) 0.0058(12) 0.0073(11) -0.0037(11) O1 0.0579(15) 0.0717(18) 0.0503(16) 0.0186(14) 0.0082(12) -0.0128(13) O3 0.0451(12) 0.0533(15) 0.0390(13) -0.0105(11) 0.0110(10) -0.0032(11) O7 0.0315(10) 0.0553(14) 0.0352(13) 0.0055(11) 0.0079(9) 0.0083(10) O8 0.0406(12) 0.0554(15) 0.0523(15) 0.0035(12) 0.0153(11) -0.0124(11) O1W 0.0442(13) 0.0479(14) 0.0436(15) 0.0063(12) 0.0155(11) 0.0001(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 Ag1 N2 2.176(2) 2_455 ? Ag1 O3 2.291(2) . ? Ag1 O7 2.3333(18) 3_655 ? Ag1 Ag2 2.8921(4) . ? Ag2 N4 2.195(2) . ? Ag2 O1W 2.399(2) . ? Ag2 O8 2.446(2) 3_655 ? Ag2 O1 2.500(2) . ? C1 C2 1.469(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N4 1.325(4) . ? C2 N3 1.362(3) . ? C3 N4 1.384(4) . ? C3 C4 1.387(4) . ? C3 C8 1.402(4) . ? C4 C5 1.375(5) . ? C4 H4 0.9300 . ? C5 C6 1.389(5) . ? C5 H5 0.9300 . ? C6 C7 1.364(5) . ? C6 H6 0.9300 . ? C7 C8 1.374(4) . ? C7 H7 0.9300 . ? C8 N3 1.384(4) . ? C9 N3 1.467(4) . ? C9 C10 1.520(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.525(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.508(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N1 1.474(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.383(4) . ? C13 N1 1.385(4) . ? C13 C18 1.404(4) . ? C14 C15 1.382(5) . ? C14 H14 0.9300 . ? C15 C16 1.384(5) . ? C15 H15 0.9300 . ? C16 C17 1.378(5) . ? C16 H16 0.9300 . ? C17 C18 1.388(4) . ? C17 H17 0.9300 . ? C18 N2 1.387(4) . ? C19 N2 1.317(4) . ? C19 N1 1.352(4) . ? C19 C20 1.479(4) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 O1 1.251(4) . ? C21 O3 1.257(4) . ? C21 C22 1.509(4) . ? C22 C27 1.397(4) . ? C22 C23 1.403(4) . ? C23 C24 1.372(5) . ? C23 H23 0.9300 . ? C24 C25 1.356(5) . ? C24 H24 0.9300 . ? C25 C26 1.396(4) . ? C25 H25 0.9300 . ? C26 C27 1.380(4) . ? C26 H26 0.9300 . ? C27 C28 1.506(4) . ? C28 O8 1.249(3) . ? C28 O7 1.255(4) . ? N2 Ag1 2.176(2) 2_445 ? O7 Ag1 2.3333(18) 3_655 ? O8 Ag2 2.446(2) 3_655 ? O1W H1E 0.854(17) . ? O1W H1F 0.864(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ag1 O3 137.56(8) 2_455 . ? N2 Ag1 O7 128.20(8) 2_455 3_655 ? O3 Ag1 O7 93.17(7) . 3_655 ? N2 Ag1 Ag2 105.17(7) 2_455 . ? O3 Ag1 Ag2 90.57(6) . . ? O7 Ag1 Ag2 78.43(6) 3_655 . ? N4 Ag2 O1W 136.43(8) . . ? N4 Ag2 O8 106.43(8) . 3_655 ? O1W Ag2 O8 87.79(8) . 3_655 ? N4 Ag2 O1 115.34(8) . . ? O1W Ag2 O1 76.95(8) . . ? O8 Ag2 O1 132.90(8) 3_655 . ? N4 Ag2 Ag1 122.57(6) . . ? O1W Ag2 Ag1 100.99(5) . . ? O8 Ag2 Ag1 70.34(6) 3_655 . ? O1 Ag2 Ag1 69.40(6) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N4 C2 N3 112.1(3) . . ? N4 C2 C1 124.5(3) . . ? N3 C2 C1 123.4(3) . . ? N4 C3 C4 130.4(3) . . ? N4 C3 C8 109.5(3) . . ? C4 C3 C8 120.0(3) . . ? C5 C4 C3 117.3(3) . . ? C5 C4 H4 121.3 . . ? C3 C4 H4 121.3 . . ? C4 C5 C6 121.8(3) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C7 C6 C5 121.5(3) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C6 C7 C8 117.2(3) . . ? C6 C7 H7 121.4 . . ? C8 C7 H7 121.4 . . ? C7 C8 N3 132.6(3) . . ? C7 C8 C3 122.1(3) . . ? N3 C8 C3 105.3(2) . . ? N3 C9 C10 113.4(2) . . ? N3 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? N3 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C9 C10 C11 110.9(2) . . ? C9 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C12 C11 C10 111.8(2) . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11B 109.3 . . ? C10 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? N1 C12 C11 112.8(2) . . ? N1 C12 H12A 109.0 . . ? C11 C12 H12A 109.0 . . ? N1 C12 H12B 109.0 . . ? C11 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C14 C13 N1 132.7(3) . . ? C14 C13 C18 121.9(3) . . ? N1 C13 C18 105.4(3) . . ? C15 C14 C13 117.0(3) . . ? C15 C14 H14 121.5 . . ? C13 C14 H14 121.5 . . ? C14 C15 C16 121.4(3) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C17 C16 C15 121.9(3) . . ? C17 C16 H16 119.0 . . ? C15 C16 H16 119.0 . . ? C16 C17 C18 117.5(3) . . ? C16 C17 H17 121.2 . . ? C18 C17 H17 121.2 . . ? N2 C18 C17 131.1(3) . . ? N2 C18 C13 108.7(2) . . ? C17 C18 C13 120.2(3) . . ? N2 C19 N1 112.3(3) . . ? N2 C19 C20 123.7(3) . . ? N1 C19 C20 124.0(3) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O1 C21 O3 125.6(3) . . ? O1 C21 C22 118.3(3) . . ? O3 C21 C22 116.1(3) . . ? C27 C22 C23 118.0(3) . . ? C27 C22 C21 123.1(2) . . ? C23 C22 C21 118.6(3) . . ? C24 C23 C22 120.7(3) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C25 C24 C23 121.1(3) . . ? C25 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? C24 C25 C26 119.6(3) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C27 C26 C25 120.2(3) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C26 C27 C22 120.4(3) . . ? C26 C27 C28 118.2(3) . . ? C22 C27 C28 121.4(3) . . ? O8 C28 O7 125.0(3) . . ? O8 C28 C27 118.3(3) . . ? O7 C28 C27 116.7(3) . . ? C19 N1 C13 107.4(2) . . ? C19 N1 C12 126.0(3) . . ? C13 N1 C12 126.6(2) . . ? C19 N2 C18 106.2(2) . . ? C19 N2 Ag1 122.5(2) . 2_445 ? C18 N2 Ag1 131.02(18) . 2_445 ? C2 N3 C8 107.3(2) . . ? C2 N3 C9 126.8(3) . . ? C8 N3 C9 125.9(2) . . ? C2 N4 C3 105.8(2) . . ? C2 N4 Ag2 123.40(19) . . ? C3 N4 Ag2 130.76(18) . . ? C21 O1 Ag2 127.4(2) . . ? C21 O3 Ag1 113.1(2) . . ? C28 O7 Ag1 112.17(17) . 3_655 ? C28 O8 Ag2 113.2(2) . 3_655 ? Ag2 O1W H1E 110(2) . . ? Ag2 O1W H1F 106(3) . . ? H1E O1W H1F 111(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Ag1 Ag2 N4 9.78(10) 2_455 . . . ? O3 Ag1 Ag2 N4 -130.33(9) . . . . ? O7 Ag1 Ag2 N4 136.55(9) 3_655 . . . ? N2 Ag1 Ag2 O1W -171.19(9) 2_455 . . . ? O3 Ag1 Ag2 O1W 48.69(8) . . . . ? O7 Ag1 Ag2 O1W -44.43(8) 3_655 . . . ? N2 Ag1 Ag2 O8 -87.58(8) 2_455 . . 3_655 ? O3 Ag1 Ag2 O8 132.31(7) . . . 3_655 ? O7 Ag1 Ag2 O8 39.19(7) 3_655 . . 3_655 ? N2 Ag1 Ag2 O1 117.39(9) 2_455 . . . ? O3 Ag1 Ag2 O1 -22.72(8) . . . . ? O7 Ag1 Ag2 O1 -115.85(8) 3_655 . . . ? N4 C3 C4 C5 177.3(3) . . . . ? C8 C3 C4 C5 0.2(4) . . . . ? C3 C4 C5 C6 2.6(5) . . . . ? C4 C5 C6 C7 -2.9(6) . . . . ? C5 C6 C7 C8 0.3(6) . . . . ? C6 C7 C8 N3 -178.8(3) . . . . ? C6 C7 C8 C3 2.5(5) . . . . ? N4 C3 C8 C7 179.5(3) . . . . ? C4 C3 C8 C7 -2.8(5) . . . . ? N4 C3 C8 N3 0.6(3) . . . . ? C4 C3 C8 N3 178.2(3) . . . . ? N3 C9 C10 C11 -174.6(3) . . . . ? C9 C10 C11 C12 -174.3(3) . . . . ? C10 C11 C12 N1 -176.2(3) . . . . ? N1 C13 C14 C15 177.6(3) . . . . ? C18 C13 C14 C15 -1.7(5) . . . . ? C13 C14 C15 C16 1.1(5) . . . . ? C14 C15 C16 C17 0.3(6) . . . . ? C15 C16 C17 C18 -1.1(5) . . . . ? C16 C17 C18 N2 -177.8(3) . . . . ? C16 C17 C18 C13 0.5(4) . . . . ? C14 C13 C18 N2 179.6(3) . . . . ? N1 C13 C18 N2 0.1(3) . . . . ? C14 C13 C18 C17 1.0(4) . . . . ? N1 C13 C18 C17 -178.5(3) . . . . ? O1 C21 C22 C27 -121.0(3) . . . . ? O3 C21 C22 C27 61.0(4) . . . . ? O1 C21 C22 C23 64.1(4) . . . . ? O3 C21 C22 C23 -113.9(3) . . . . ? C27 C22 C23 C24 0.1(4) . . . . ? C21 C22 C23 C24 175.3(3) . . . . ? C22 C23 C24 C25 -1.3(5) . . . . ? C23 C24 C25 C26 1.2(5) . . . . ? C24 C25 C26 C27 0.2(5) . . . . ? C25 C26 C27 C22 -1.4(4) . . . . ? C25 C26 C27 C28 175.4(3) . . . . ? C23 C22 C27 C26 1.2(4) . . . . ? C21 C22 C27 C26 -173.7(3) . . . . ? C23 C22 C27 C28 -175.4(3) . . . . ? C21 C22 C27 C28 9.6(4) . . . . ? C26 C27 C28 O8 40.4(4) . . . . ? C22 C27 C28 O8 -142.8(3) . . . . ? C26 C27 C28 O7 -137.3(3) . . . . ? C22 C27 C28 O7 39.5(4) . . . . ? N2 C19 N1 C13 -1.3(3) . . . . ? C20 C19 N1 C13 178.1(3) . . . . ? N2 C19 N1 C12 177.6(3) . . . . ? C20 C19 N1 C12 -3.0(5) . . . . ? C14 C13 N1 C19 -178.7(3) . . . . ? C18 C13 N1 C19 0.7(3) . . . . ? C14 C13 N1 C12 2.4(5) . . . . ? C18 C13 N1 C12 -178.2(3) . . . . ? C11 C12 N1 C19 77.9(4) . . . . ? C11 C12 N1 C13 -103.5(3) . . . . ? N1 C19 N2 C18 1.3(3) . . . . ? C20 C19 N2 C18 -178.1(3) . . . . ? N1 C19 N2 Ag1 -173.59(18) . . . 2_445 ? C20 C19 N2 Ag1 7.0(4) . . . 2_445 ? C17 C18 N2 C19 177.6(3) . . . . ? C13 C18 N2 C19 -0.9(3) . . . . ? C17 C18 N2 Ag1 -8.1(5) . . . 2_445 ? C13 C18 N2 Ag1 173.47(19) . . . 2_445 ? N4 C2 N3 C8 1.3(3) . . . . ? C1 C2 N3 C8 -178.1(3) . . . . ? N4 C2 N3 C9 -178.5(3) . . . . ? C1 C2 N3 C9 2.1(5) . . . . ? C7 C8 N3 C2 -179.9(3) . . . . ? C3 C8 N3 C2 -1.1(3) . . . . ? C7 C8 N3 C9 -0.1(5) . . . . ? C3 C8 N3 C9 178.7(3) . . . . ? C10 C9 N3 C2 -85.2(4) . . . . ? C10 C9 N3 C8 95.0(3) . . . . ? N3 C2 N4 C3 -0.9(3) . . . . ? C1 C2 N4 C3 178.4(3) . . . . ? N3 C2 N4 Ag2 176.20(18) . . . . ? C1 C2 N4 Ag2 -4.5(4) . . . . ? C4 C3 N4 C2 -177.1(3) . . . . ? C8 C3 N4 C2 0.2(3) . . . . ? C4 C3 N4 Ag2 6.0(5) . . . . ? C8 C3 N4 Ag2 -176.62(19) . . . . ? O1W Ag2 N4 C2 -69.4(3) . . . . ? O8 Ag2 N4 C2 -174.0(2) 3_655 . . . ? O1 Ag2 N4 C2 28.3(2) . . . . ? Ag1 Ag2 N4 C2 109.2(2) . . . . ? O1W Ag2 N4 C3 106.9(2) . . . . ? O8 Ag2 N4 C3 2.3(3) 3_655 . . . ? O1 Ag2 N4 C3 -155.3(2) . . . . ? Ag1 Ag2 N4 C3 -74.5(2) . . . . ? O3 C21 O1 Ag2 -30.5(4) . . . . ? C22 C21 O1 Ag2 151.7(2) . . . . ? N4 Ag2 O1 C21 155.1(3) . . . . ? O1W Ag2 O1 C21 -69.4(3) . . . . ? O8 Ag2 O1 C21 5.0(3) 3_655 . . . ? Ag1 Ag2 O1 C21 37.8(3) . . . . ? O1 C21 O3 Ag1 -4.8(4) . . . . ? C22 C21 O3 Ag1 173.05(18) . . . . ? N2 Ag1 O3 C21 -87.3(2) 2_455 . . . ? O7 Ag1 O3 C21 104.59(19) 3_655 . . . ? Ag2 Ag1 O3 C21 26.15(18) . . . . ? O8 C28 O7 Ag1 -15.4(4) . . . 3_655 ? C27 C28 O7 Ag1 162.15(19) . . . 3_655 ? O7 C28 O8 Ag2 -39.0(4) . . . 3_655 ? C27 C28 O8 Ag2 143.5(2) . . . 3_655 ? 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 H1F O7 0.864(17) 1.99(2) 2.779(3) 152(3) . O1W H1E O3 0.854(17) 2.00(2) 2.784(3) 152(3) 3_655 _diffrn_measured_fraction_theta_max 0.865 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.066 _refine_diff_density_min -0.747 _refine_diff_density_rms 0.073 #==== data_1_Ag _database_code_depnum_ccdc_archive 'CCDC 806442' #TrackingRef '- crystals.cif' #0 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H17 Ag N2 O4' _chemical_formula_weight 385.17 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' Ag Ag -0.8971 1.1015 '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 ' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7504(8) _cell_length_b 9.8666(8) _cell_length_c 10.0927(7) _cell_angle_alpha 92.064(6) _cell_angle_beta 114.696(7) _cell_angle_gamma 119.342(9) _cell_volume 732.59(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3338 _cell_measurement_theta_min 4.2 _cell_measurement_theta_max 29.2 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.746 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 1.393 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.58 _exptl_absorpt_correction_T_max 0.64 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5476 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0953 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_max 29.18 _reflns_number_total 3356 _reflns_number_gt 1805 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. H atoms of water molecules were refined isotropically with distance restraints of O---H = 0.89+-0.02 \%A. The distances of H1D...H1E and H2D...H2E were restrained to 1.44+-0.02 \%A. ; _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^)+(0.0267P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3356 _refine_ls_number_parameters 203 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0953 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.0735 _refine_ls_wR_factor_gt 0.0657 _refine_ls_goodness_of_fit_ref 0.833 _refine_ls_restrained_S_all 0.833 _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 Ag1 Ag 0.19173(5) -0.30489(5) 0.54987(4) 0.06180(15) Uani 1 1 d . . . C1 C 0.0329(6) -0.0890(6) 0.3665(5) 0.0749(14) Uani 1 1 d . . . H1A H -0.0819 -0.1455 0.2731 0.112 Uiso 1 1 calc R . . H1B H 0.0726 0.0223 0.4013 0.112 Uiso 1 1 calc R . . H1C H 0.0198 -0.1411 0.4430 0.112 Uiso 1 1 calc R . . C2 C 0.1688(5) -0.0935(5) 0.3391(4) 0.0459(10) Uani 1 1 d . . . C3 C 0.3575(4) -0.0447(4) 0.2521(4) 0.0402(9) Uani 1 1 d . . . C4 C 0.4666(5) 0.0072(5) 0.1864(4) 0.0509(10) Uani 1 1 d . . . H4 H 0.4715 0.0824 0.1325 0.061 Uiso 1 1 calc R . . C5 C 0.5668(5) -0.0579(6) 0.2048(5) 0.0655(13) Uani 1 1 d . . . H5 H 0.6420 -0.0259 0.1625 0.079 Uiso 1 1 calc R . . C6 C 0.5589(5) -0.1705(6) 0.2851(5) 0.0634(12) Uani 1 1 d . . . H6 H 0.6280 -0.2129 0.2942 0.076 Uiso 1 1 calc R . . C7 C 0.4521(5) -0.2205(5) 0.3511(4) 0.0492(10) Uani 1 1 d . . . H7 H 0.4477 -0.2956 0.4051 0.059 Uiso 1 1 calc R . . C8 C 0.3510(4) -0.1549(4) 0.3343(4) 0.0337(8) Uani 1 1 d . . . C9 C 0.2207(6) 0.1210(5) 0.1983(4) 0.0611(12) Uani 1 1 d . . . H8A H 0.3391 0.2150 0.2245 0.073 Uiso 1 1 calc R . . H8B H 0.1701 0.1558 0.2456 0.073 Uiso 1 1 calc R . . C10 C 0.0957(5) 0.0575(5) 0.0228(5) 0.0666(12) Uani 1 1 d . . . H9A H 0.1088 0.1492 -0.0157 0.080 Uiso 1 1 calc R . . H9B H 0.1332 0.0039 -0.0230 0.080 Uiso 1 1 calc R . . C11 C 0.0679(5) -0.3876(5) 0.7594(4) 0.0449(10) Uani 1 1 d . . . C12 C 0.0360(4) -0.4434(4) 0.8857(4) 0.0382(9) Uani 1 1 d . . . C13 C 0.1199(5) -0.5141(5) 0.9725(4) 0.0471(10) Uani 1 1 d . . . H12 H 0.2008 -0.5245 0.9544 0.057 Uiso 1 1 calc R . . C14 C 0.0849(5) -0.5685(5) 1.0840(4) 0.0473(10) Uani 1 1 d . . . H13 H 0.1433 -0.6148 1.1412 0.057 Uiso 1 1 calc R . . N1 N 0.2303(4) -0.1851(4) 0.3863(3) 0.0398(7) Uani 1 1 d . . . N2 N 0.2417(4) -0.0051(4) 0.2592(3) 0.0448(8) Uani 1 1 d . . . O1 O -0.0134(4) -0.3287(4) 0.6818(3) 0.0708(9) Uani 1 1 d . . . O2 O 0.1788(4) -0.4028(3) 0.7369(3) 0.0565(7) Uani 1 1 d . . . O1W O -0.3738(5) -0.4611(5) 0.4528(4) 0.0954(11) Uani 1 1 d D . . H1D H -0.381(7) -0.455(7) 0.365(3) 0.143 Uiso 1 1 d D . . H1E H -0.262(4) -0.407(7) 0.528(4) 0.143 Uiso 1 1 d D . . O2W O 0.4533(5) -0.4590(6) 0.8571(4) 0.1050(12) Uani 1 1 d D . . H2D H 0.354(5) -0.549(4) 0.840(7) 0.157 Uiso 1 1 d D . . H2E H 0.514(7) -0.395(6) 0.951(4) 0.157 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.0679(2) 0.0750(3) 0.04681(19) 0.03471(16) 0.04122(16) 0.03122(19) C1 0.070(3) 0.124(4) 0.060(3) 0.027(3) 0.040(2) 0.067(3) C2 0.046(2) 0.066(3) 0.032(2) 0.017(2) 0.0239(18) 0.032(2) C3 0.039(2) 0.049(3) 0.0282(19) 0.0157(18) 0.0183(16) 0.020(2) C4 0.048(2) 0.058(3) 0.034(2) 0.020(2) 0.0243(18) 0.018(2) C5 0.049(2) 0.087(4) 0.051(3) 0.010(3) 0.035(2) 0.023(3) C6 0.053(3) 0.080(4) 0.067(3) 0.016(3) 0.033(2) 0.041(3) C7 0.047(2) 0.046(3) 0.049(2) 0.014(2) 0.024(2) 0.022(2) C8 0.0338(18) 0.048(2) 0.0299(18) 0.0173(17) 0.0177(16) 0.028(2) C9 0.072(3) 0.052(3) 0.050(2) 0.018(2) 0.015(2) 0.041(2) C10 0.080(3) 0.074(3) 0.066(3) 0.043(3) 0.037(3) 0.053(3) C11 0.043(2) 0.048(3) 0.031(2) 0.0156(19) 0.0219(18) 0.015(2) C12 0.039(2) 0.044(2) 0.036(2) 0.0198(18) 0.0238(17) 0.0210(19) C13 0.055(2) 0.063(3) 0.046(2) 0.027(2) 0.037(2) 0.037(2) C14 0.060(2) 0.064(3) 0.052(2) 0.041(2) 0.040(2) 0.045(2) N1 0.0400(16) 0.052(2) 0.0279(15) 0.0182(15) 0.0208(13) 0.0224(17) N2 0.0524(18) 0.057(2) 0.0313(17) 0.0194(16) 0.0206(15) 0.0344(18) O1 0.0727(19) 0.112(3) 0.0623(18) 0.0643(18) 0.0473(16) 0.060(2) O2 0.0709(18) 0.083(2) 0.0570(17) 0.0466(16) 0.0527(15) 0.0512(18) O1W 0.084(2) 0.146(3) 0.080(2) 0.052(3) 0.044(2) 0.075(3) O2W 0.110(3) 0.161(4) 0.104(3) 0.072(3) 0.073(3) 0.096(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N1 2.118(3) . ? Ag1 O2 2.173(2) . ? C1 C2 1.482(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N1 1.314(4) . ? C2 N2 1.357(4) . ? C3 C4 1.383(5) . ? C3 C8 1.384(5) . ? C3 N2 1.390(4) . ? C4 C5 1.369(5) . ? C4 H4 0.9300 . ? C5 C6 1.389(6) . ? C5 H5 0.9300 . ? C6 C7 1.368(6) . ? C6 H6 0.9300 . ? C7 C8 1.384(5) . ? C7 H7 0.9300 . ? C8 N1 1.390(4) . ? C9 N2 1.472(4) . ? C9 C10 1.544(5) . ? C9 H8A 0.9700 . ? C9 H8B 0.9700 . ? C10 C10 1.466(8) 2 ? C10 H9A 0.9700 . ? C10 H9B 0.9700 . ? C11 O1 1.243(4) . ? C11 O2 1.267(4) . ? C11 C12 1.496(5) . ? C12 C13 1.388(4) . ? C12 C14 1.391(5) 2_547 ? C13 C14 1.362(5) . ? C13 H12 0.9300 . ? C14 C12 1.391(5) 2_547 ? C14 H13 0.9300 . ? O1W H1D 0.863(19) . ? O1W H1E 0.871(19) . ? O2W H2D 0.874(19) . ? O2W H2E 0.876(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ag1 O2 173.66(11) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 N2 112.0(3) . . ? N1 C2 C1 124.4(4) . . ? N2 C2 C1 123.6(3) . . ? C4 C3 C8 122.2(3) . . ? C4 C3 N2 132.7(3) . . ? C8 C3 N2 105.0(3) . . ? C5 C4 C3 116.5(4) . . ? C5 C4 H4 121.7 . . ? C3 C4 H4 121.7 . . ? C4 C5 C6 121.7(4) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C7 C6 C5 121.7(4) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C6 C7 C8 117.3(4) . . ? C6 C7 H7 121.3 . . ? C8 C7 H7 121.3 . . ? C7 C8 C3 120.6(3) . . ? C7 C8 N1 129.6(3) . . ? C3 C8 N1 109.8(3) . . ? N2 C9 C10 111.7(3) . . ? N2 C9 H8A 109.3 . . ? C10 C9 H8A 109.3 . . ? N2 C9 H8B 109.3 . . ? C10 C9 H8B 109.3 . . ? H8A C9 H8B 107.9 . . ? C10 C10 C9 112.1(5) 2 . ? C10 C10 H9A 109.2 2 . ? C9 C10 H9A 109.2 . . ? C10 C10 H9B 109.2 2 . ? C9 C10 H9B 109.2 . . ? H9A C10 H9B 107.9 . . ? O1 C11 O2 122.8(3) . . ? O1 C11 C12 119.6(3) . . ? O2 C11 C12 117.6(3) . . ? C13 C12 C14 117.7(3) . 2_547 ? C13 C12 C11 121.6(3) . . ? C14 C12 C11 120.6(3) 2_547 . ? C14 C13 C12 120.7(3) . . ? C14 C13 H12 119.6 . . ? C12 C13 H12 119.6 . . ? C13 C14 C12 121.6(3) . 2_547 ? C13 C14 H13 119.2 . . ? C12 C14 H13 119.2 2_547 . ? C2 N1 C8 105.7(3) . . ? C2 N1 Ag1 123.7(2) . . ? C8 N1 Ag1 129.2(2) . . ? C2 N2 C3 107.5(3) . . ? C2 N2 C9 129.0(3) . . ? C3 N2 C9 123.3(3) . . ? C11 O2 Ag1 106.5(2) . . ? H1D O1W H1E 113(3) . . ? H2D O2W H2E 111(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 C3 C4 C5 0.9(5) . . . . ? N2 C3 C4 C5 178.9(4) . . . . ? C3 C4 C5 C6 0.1(6) . . . . ? C4 C5 C6 C7 -0.7(6) . . . . ? C5 C6 C7 C8 0.2(6) . . . . ? C6 C7 C8 C3 0.8(5) . . . . ? C6 C7 C8 N1 178.8(3) . . . . ? C4 C3 C8 C7 -1.4(5) . . . . ? N2 C3 C8 C7 -179.9(3) . . . . ? C4 C3 C8 N1 -179.8(3) . . . . ? N2 C3 C8 N1 1.7(4) . . . . ? N2 C9 C10 C10 72.9(6) . . . 2 ? O1 C11 C12 C13 178.1(3) . . . . ? O2 C11 C12 C13 -1.9(5) . . . . ? O1 C11 C12 C14 0.6(5) . . . 2_547 ? O2 C11 C12 C14 -179.5(3) . . . 2_547 ? C14 C12 C13 C14 -0.4(6) 2_547 . . . ? C11 C12 C13 C14 -178.1(4) . . . . ? C12 C13 C14 C12 0.4(6) . . . 2_547 ? N2 C2 N1 C8 0.1(4) . . . . ? C1 C2 N1 C8 178.8(3) . . . . ? N2 C2 N1 Ag1 167.5(2) . . . . ? C1 C2 N1 Ag1 -13.7(5) . . . . ? C7 C8 N1 C2 -179.3(3) . . . . ? C3 C8 N1 C2 -1.1(4) . . . . ? C7 C8 N1 Ag1 14.1(5) . . . . ? C3 C8 N1 Ag1 -167.7(2) . . . . ? N1 C2 N2 C3 1.0(4) . . . . ? C1 C2 N2 C3 -177.8(3) . . . . ? N1 C2 N2 C9 -174.4(3) . . . . ? C1 C2 N2 C9 6.8(6) . . . . ? C4 C3 N2 C2 -179.9(4) . . . . ? C8 C3 N2 C2 -1.6(4) . . . . ? C4 C3 N2 C9 -4.1(6) . . . . ? C8 C3 N2 C9 174.1(3) . . . . ? C10 C9 N2 C2 -106.2(5) . . . . ? C10 C9 N2 C3 79.1(4) . . . . ? O1 C11 O2 Ag1 1.0(4) . . . . ? C12 C11 O2 Ag1 -178.9(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 O1W H1E O1 0.871(19) 1.95(2) 2.809(4) 168(6) . O1W H1D O2W 0.863(19) 2.05(3) 2.864(5) 156(6) 2_546 _diffrn_measured_fraction_theta_max 0.846 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.409 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.073 #==== data_1_Ag5 _database_code_depnum_ccdc_archive 'CCDC 806443' #TrackingRef '- crystals.cif' #1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C98 H111 Ag5 N18 O13' _chemical_formula_weight 2288.40 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' Ag Ag -0.8971 1.1015 '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 ' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.6759(3) _cell_length_b 13.2549(4) _cell_length_c 19.1940(5) _cell_angle_alpha 87.414(2) _cell_angle_beta 85.056(2) _cell_angle_gamma 86.352(2) _cell_volume 2951.12(14) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13507 _cell_measurement_theta_min 4.5 _cell_measurement_theta_max 29.3 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1164 _exptl_absorpt_coefficient_mu 0.873 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.72 _exptl_absorpt_correction_T_max 0.75 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _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 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21868 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.1064 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.52 _diffrn_reflns_theta_max 29.30 _reflns_number_total 13507 _reflns_number_gt 5855 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.1024P)^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 13507 _refine_ls_number_parameters 650 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1365 _refine_ls_R_factor_gt 0.0601 _refine_ls_wR_factor_ref 0.1791 _refine_ls_wR_factor_gt 0.1574 _refine_ls_goodness_of_fit_ref 0.841 _refine_ls_restrained_S_all 0.841 _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 Ag1 Ag 0.5000 0.5000 0.5000 0.0737(2) Uani 1 2 d S . . Ag2 Ag 0.77240(4) 1.21405(3) 0.02566(2) 0.05703(16) Uani 1 1 d . . . Ag3 Ag 0.76162(5) 1.39149(5) 0.54511(2) 0.0884(2) Uani 1 1 d . . . C1 C 0.6545(5) 0.4441(5) 0.3627(3) 0.0506(14) Uani 1 1 d . . . C2 C 0.6561(6) 0.3387(5) 0.3690(3) 0.0673(18) Uani 1 1 d . . . H2 H 0.6221 0.3059 0.4087 0.081 Uiso 1 1 calc R . . C3 C 0.7092(6) 0.2859(5) 0.3152(4) 0.0767(19) Uani 1 1 d . . . H3 H 0.7102 0.2157 0.3180 0.092 Uiso 1 1 calc R . . C4 C 0.7625(6) 0.3335(6) 0.2556(4) 0.0713(17) Uani 1 1 d . . . H4 H 0.7989 0.2946 0.2201 0.086 Uiso 1 1 calc R . . C5 C 0.7617(5) 0.4377(5) 0.2492(3) 0.0637(17) Uani 1 1 d . . . H5 H 0.7956 0.4701 0.2094 0.076 Uiso 1 1 calc R . . C6 C 0.7085(5) 0.4923(5) 0.3042(3) 0.0498(13) Uani 1 1 d . . . C7 C 0.6290(5) 0.6056(5) 0.3765(3) 0.0595(15) Uani 1 1 d . . . C8 C 0.5905(7) 0.7087(6) 0.4062(3) 0.081(2) Uani 1 1 d . . . H8A H 0.5160 0.7300 0.3914 0.121 Uiso 1 1 calc R . . H8B H 0.6449 0.7574 0.3894 0.121 Uiso 1 1 calc R . . H8C H 0.5865 0.7034 0.4564 0.121 Uiso 1 1 calc R . . C9 C 0.7247(5) 0.6772(5) 0.2637(3) 0.0596(15) Uani 1 1 d . . . H9A H 0.7900 0.6538 0.2327 0.072 Uiso 1 1 calc R . . H9B H 0.7487 0.7319 0.2899 0.072 Uiso 1 1 calc R . . C10 C 0.6288(5) 0.7166(4) 0.2207(3) 0.0584(15) Uani 1 1 d . . . H10A H 0.6055 0.6624 0.1937 0.070 Uiso 1 1 calc R . . H10B H 0.5629 0.7395 0.2515 0.070 Uiso 1 1 calc R . . C11 C 0.6657(5) 0.8020(4) 0.1723(3) 0.0574(15) Uani 1 1 d . . . H11A H 0.7200 0.7753 0.1356 0.069 Uiso 1 1 calc R . . H11B H 0.7056 0.8482 0.1981 0.069 Uiso 1 1 calc R . . C12 C 0.5677(5) 0.8604(5) 0.1390(3) 0.0684(18) Uani 1 1 d . . . H12A H 0.5216 0.8136 0.1179 0.082 Uiso 1 1 calc R . . H12B H 0.5188 0.8953 0.1748 0.082 Uiso 1 1 calc R . . C13 C 0.6585(7) 1.0673(5) 0.1662(3) 0.083(2) Uani 1 1 d . . . H13A H 0.7242 1.0386 0.1885 0.124 Uiso 1 1 calc R . . H13B H 0.5894 1.0524 0.1947 0.124 Uiso 1 1 calc R . . H13C H 0.6632 1.1393 0.1606 0.124 Uiso 1 1 calc R . . C14 C 0.6563(5) 1.0241(4) 0.0975(3) 0.0572(15) Uani 1 1 d . . . C15 C 0.6252(4) 0.9209(4) 0.0137(3) 0.0498(13) Uani 1 1 d . . . C16 C 0.6789(4) 1.0055(4) -0.0154(3) 0.0496(13) Uani 1 1 d . . . C17 C 0.7027(5) 1.0188(5) -0.0868(3) 0.0617(16) Uani 1 1 d . . . H17 H 0.7377 1.0757 -0.1065 0.074 Uiso 1 1 calc R . . C18 C 0.6716(6) 0.9424(6) -0.1283(4) 0.0780(19) Uani 1 1 d . . . H18 H 0.6860 0.9486 -0.1766 0.094 Uiso 1 1 calc R . . C19 C 0.6194(5) 0.8572(5) -0.0983(4) 0.0711(18) Uani 1 1 d . . . H19 H 0.6011 0.8073 -0.1274 0.085 Uiso 1 1 calc R . . C20 C 0.5943(5) 0.8444(4) -0.0282(4) 0.0625(16) Uani 1 1 d . . . H20 H 0.5585 0.7877 -0.0088 0.075 Uiso 1 1 calc R . . C21 C 0.9985(5) 1.2893(4) 0.0806(3) 0.0519(14) Uani 1 1 d . . . C22 C 1.0514(6) 1.1857(5) 0.0836(4) 0.081(2) Uani 1 1 d . . . H22A H 1.0630 1.1657 0.1313 0.122 Uiso 1 1 calc R . . H22B H 1.1241 1.1833 0.0562 0.122 Uiso 1 1 calc R . . H22C H 1.0015 1.1404 0.0653 0.122 Uiso 1 1 calc R . . C23 C 0.8776(5) 1.4194(4) 0.0672(2) 0.0462(13) Uani 1 1 d . . . C24 C 0.9781(5) 1.4535(5) 0.0892(2) 0.0548(15) Uani 1 1 d . . . C25 C 0.9903(6) 1.5587(5) 0.0969(3) 0.0642(17) Uani 1 1 d . . . H25 H 1.0573 1.5834 0.1107 0.077 Uiso 1 1 calc R . . C26 C 0.8963(7) 1.6206(5) 0.0826(3) 0.073(2) Uani 1 1 d . . . H26 H 0.8995 1.6898 0.0879 0.088 Uiso 1 1 calc R . . C27 C 0.7964(6) 1.5854(5) 0.0606(3) 0.0660(16) Uani 1 1 d . . . H27 H 0.7356 1.6313 0.0510 0.079 Uiso 1 1 calc R . . C28 C 0.7856(5) 1.4844(5) 0.0528(3) 0.0573(15) Uani 1 1 d . . . H28 H 0.7186 1.4607 0.0384 0.069 Uiso 1 1 calc R . . C29 C 1.1713(5) 1.3729(6) 0.1204(3) 0.0685(18) Uani 1 1 d . . . C30 C 1.1746(5) 1.3378(6) 0.1986(3) 0.0694(18) Uani 1 1 d . . . H30A H 1.1589 1.2667 0.2038 0.083 Uiso 1 1 calc R . . H30B H 1.2513 1.3449 0.2129 0.083 Uiso 1 1 calc R . . C31 C 1.0875(5) 1.3981(6) 0.2467(3) 0.0727(18) Uani 1 1 d . . . H31A H 1.0931 1.4699 0.2356 0.087 Uiso 1 1 calc R . . H31B H 1.0102 1.3807 0.2391 0.087 Uiso 1 1 calc R . . C32 C 1.1094(5) 1.3759(6) 0.3218(3) 0.0702(18) Uani 1 1 d . . . H32A H 1.1172 1.3032 0.3302 0.084 Uiso 1 1 calc R . . H32B H 1.1816 1.4034 0.3306 0.084 Uiso 1 1 calc R . . C33 C 0.9480(7) 1.2534(6) 0.4219(4) 0.082(2) Uani 1 1 d . . . H33A H 0.8896 1.2315 0.4566 0.124 Uiso 1 1 calc R . . H33B H 1.0223 1.2272 0.4347 0.124 Uiso 1 1 calc R . . H33C H 0.9344 1.2289 0.3773 0.124 Uiso 1 1 calc R . . C34 C 0.9448(5) 1.3640(5) 0.4179(3) 0.0603(16) Uani 1 1 d . . . C35 C 0.9039(5) 1.5231(6) 0.4370(3) 0.0606(16) Uani 1 1 d . . . C36 C 0.9921(5) 1.5196(5) 0.3821(3) 0.0588(15) Uani 1 1 d . . . C37 C 1.0387(6) 1.6054(7) 0.3514(4) 0.078(2) Uani 1 1 d . . . H37 H 1.0981 1.6017 0.3159 0.094 Uiso 1 1 calc R . . C38 C 0.8586(6) 1.6131(6) 0.4618(4) 0.0764(19) Uani 1 1 d . . . H38 H 0.8005 1.6160 0.4981 0.092 Uiso 1 1 calc R . . C39 C 0.9931(8) 1.6970(7) 0.3758(5) 0.095(2) Uani 1 1 d . . . H39 H 1.0220 1.7564 0.3559 0.114 Uiso 1 1 calc R . . C40 C 0.9043(8) 1.7030(6) 0.4296(5) 0.092(2) Uani 1 1 d . . . H40 H 0.8749 1.7660 0.4446 0.110 Uiso 1 1 calc R . . C41 C 0.6398(5) 1.4628(6) -0.3318(3) 0.0558(15) Uani 1 1 d . . . C42 C 0.6630(5) 1.3409(4) -0.0806(3) 0.0517(14) Uani 1 1 d . . . C43 C 0.6076(4) 1.4752(4) -0.2549(2) 0.0447(12) Uani 1 1 d . . . C44 C 0.6468(4) 1.4026(4) -0.2058(2) 0.0493(13) Uani 1 1 d . . . H44 H 0.6911 1.3456 -0.2207 0.059 Uiso 1 1 calc R . . C45 C 0.6191(4) 1.4159(4) -0.1347(2) 0.0475(14) Uani 1 1 d . . . C46 C 0.5508(4) 1.4992(4) -0.1132(3) 0.0459(13) Uani 1 1 d . . . H46 H 0.5302 1.5061 -0.0656 0.055 Uiso 1 1 calc R . . C47 C 0.5118(4) 1.5733(4) -0.1607(3) 0.0492(14) Uani 1 1 d . . . C48 C 0.5424(5) 1.5574(5) -0.2324(3) 0.0504(14) Uani 1 1 d . . . H48 H 0.5168 1.6053 -0.2654 0.061 Uiso 1 1 calc R . . N1 N 0.6901(4) 0.5926(4) 0.3134(2) 0.0515(11) Uani 1 1 d . . . N2 N 0.6063(4) 0.5183(4) 0.4076(2) 0.0571(12) Uani 1 1 d . . . N3 N 0.6104(4) 0.9343(3) 0.0852(2) 0.0547(12) Uani 1 1 d . . . N4 N 0.6973(4) 1.0692(3) 0.0382(3) 0.0568(12) Uani 1 1 d . . . N5 N 0.8937(4) 1.3145(3) 0.0623(2) 0.0502(11) Uani 1 1 d . . . N6 N 1.0534(4) 1.3698(4) 0.0973(2) 0.0534(12) Uani 1 1 d . . . N7 N 1.0166(4) 1.4187(4) 0.3715(2) 0.0621(13) Uani 1 1 d . . . N8 N 0.8767(4) 1.4255(4) 0.4572(2) 0.0612(13) Uani 1 1 d . . . N9 N 0.4492(4) 1.6607(4) -0.1387(3) 0.0655(13) Uani 1 1 d . . . H9N H 0.4337 1.6700 -0.0948 0.098 Uiso 1 1 calc R . . H9M H 0.4260 1.7054 -0.1691 0.098 Uiso 1 1 calc R . . O1 O 0.6422(4) 1.5388(4) -0.3721(2) 0.0747(12) Uani 1 1 d . . . O2 O 0.6671(4) 1.3753(4) -0.3523(2) 0.0721(12) Uani 1 1 d . . . O3 O 0.6113(4) 1.3369(3) -0.02107(18) 0.0646(11) Uani 1 1 d . . . O4 O 0.7506(4) 1.2849(4) -0.0974(2) 0.0811(13) Uani 1 1 d . . . O5 O 0.8627(7) 0.1913(7) 0.7921(4) 0.068(2) Uani 0.50 1 d P . . H5A H 0.8241 0.2137 0.8264 0.102 Uiso 0.50 1 calc PR . . C50 C 1.0087(14) 0.1071(15) 0.8730(11) 0.128(7) Uani 0.50 1 d P . . H50A H 1.0895 0.1037 0.8794 0.192 Uiso 0.50 1 calc PR . . H50B H 0.9855 0.0408 0.8649 0.192 Uiso 0.50 1 calc PR . . H50C H 0.9660 0.1325 0.9142 0.192 Uiso 0.50 1 calc PR . . C49 C 0.983(3) 0.1827(18) 0.8057(8) 0.194(17) Uani 0.50 1 d P . . H49A H 1.0080 0.2494 0.8140 0.233 Uiso 0.50 1 calc PR . . H49B H 1.0286 0.1578 0.7646 0.233 Uiso 0.50 1 calc PR . . O1W O 0.6949(10) 0.1813(6) 0.6923(5) 0.087(3) Uani 0.50 1 d P . . O2W O 0.7244(11) 0.1746(8) 0.5419(6) 0.111(4) Uani 0.50 1 d P . . O3W O 0.5288(15) 0.1336(10) 0.4765(7) 0.061(4) Uani 0.25 1 d P . . O4W O 0.5452(18) 0.0277(13) 0.6923(8) 0.086(6) Uani 0.25 1 d P . . O6 O 0.6326(9) 0.7445(7) 0.5948(5) 0.087(3) Uani 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 Ag1 0.0749(5) 0.0982(6) 0.0434(3) 0.0085(3) 0.0147(3) -0.0036(4) Ag2 0.0588(3) 0.0481(3) 0.0657(3) -0.0004(2) -0.0105(2) -0.0092(2) Ag3 0.0797(4) 0.1390(6) 0.0437(3) -0.0005(3) 0.0108(2) -0.0071(4) C1 0.048(3) 0.067(4) 0.035(3) 0.003(3) -0.006(2) 0.003(3) C2 0.070(4) 0.077(5) 0.056(4) 0.014(3) -0.014(3) -0.013(4) C3 0.085(5) 0.062(4) 0.084(5) -0.012(4) -0.019(4) 0.004(4) C4 0.066(4) 0.079(5) 0.069(4) -0.020(4) -0.002(3) 0.008(4) C5 0.053(3) 0.092(5) 0.045(3) -0.001(3) -0.005(3) 0.002(3) C6 0.049(3) 0.064(4) 0.037(3) 0.004(3) -0.008(2) -0.001(3) C7 0.053(3) 0.078(4) 0.046(3) 0.002(3) -0.005(3) 0.007(3) C8 0.093(5) 0.089(5) 0.059(4) -0.007(4) -0.001(4) 0.008(4) C9 0.055(3) 0.069(4) 0.054(3) 0.013(3) 0.001(3) -0.009(3) C10 0.054(3) 0.062(4) 0.058(3) 0.013(3) -0.009(3) 0.000(3) C11 0.050(3) 0.050(3) 0.070(4) 0.012(3) 0.001(3) -0.006(3) C12 0.056(4) 0.065(4) 0.080(4) 0.023(3) 0.005(3) -0.006(3) C13 0.118(6) 0.066(4) 0.064(4) 0.001(3) -0.014(4) 0.002(4) C14 0.058(3) 0.049(3) 0.064(4) 0.004(3) -0.013(3) 0.000(3) C15 0.040(3) 0.045(3) 0.064(4) 0.006(3) -0.008(3) 0.002(3) C16 0.042(3) 0.047(3) 0.061(3) 0.001(3) -0.011(3) -0.001(3) C17 0.049(3) 0.068(4) 0.067(4) 0.008(3) -0.011(3) -0.004(3) C18 0.076(4) 0.092(5) 0.067(4) -0.004(4) -0.017(3) 0.008(4) C19 0.063(4) 0.069(4) 0.085(5) -0.014(4) -0.019(4) -0.006(3) C20 0.050(3) 0.047(3) 0.092(5) 0.002(3) -0.016(3) -0.005(3) C21 0.054(3) 0.055(4) 0.048(3) -0.008(3) -0.009(3) -0.004(3) C22 0.075(5) 0.076(5) 0.093(5) -0.014(4) -0.019(4) 0.004(4) C23 0.050(3) 0.053(3) 0.035(3) 0.002(2) 0.003(2) -0.010(3) C24 0.066(4) 0.068(4) 0.031(3) -0.008(3) 0.009(2) -0.023(4) C25 0.077(4) 0.060(4) 0.055(3) -0.019(3) 0.020(3) -0.022(4) C26 0.112(6) 0.043(4) 0.061(4) -0.014(3) 0.031(4) -0.009(4) C27 0.082(5) 0.057(4) 0.056(3) -0.007(3) 0.010(3) 0.006(4) C28 0.064(4) 0.060(4) 0.046(3) -0.003(3) 0.007(3) -0.003(3) C29 0.044(3) 0.120(6) 0.044(3) -0.017(3) -0.004(2) -0.019(4) C30 0.043(3) 0.110(5) 0.056(3) -0.017(3) -0.004(3) -0.004(3) C31 0.056(4) 0.112(5) 0.050(3) -0.014(3) 0.003(3) -0.005(4) C32 0.054(4) 0.109(5) 0.047(3) -0.016(3) -0.005(3) 0.006(4) C33 0.086(5) 0.094(6) 0.069(4) 0.001(4) -0.010(4) -0.012(4) C34 0.060(4) 0.086(5) 0.037(3) -0.004(3) -0.008(3) -0.008(4) C35 0.058(4) 0.088(5) 0.039(3) -0.016(3) -0.012(3) -0.002(4) C36 0.058(4) 0.078(5) 0.041(3) -0.004(3) -0.010(3) -0.005(3) C37 0.072(4) 0.098(6) 0.066(4) 0.013(4) -0.014(3) -0.010(5) C38 0.072(4) 0.102(6) 0.057(4) -0.019(4) -0.017(3) 0.008(4) C39 0.102(6) 0.094(6) 0.092(6) 0.016(5) -0.030(5) -0.015(5) C40 0.113(7) 0.075(5) 0.093(6) -0.016(5) -0.051(5) 0.018(5) C41 0.045(3) 0.075(4) 0.046(3) 0.001(3) 0.001(2) -0.002(3) C42 0.057(4) 0.052(3) 0.048(3) 0.000(3) -0.012(3) -0.007(3) C43 0.041(3) 0.056(3) 0.038(3) 0.000(2) -0.001(2) -0.006(3) C44 0.043(3) 0.067(4) 0.038(3) -0.003(3) -0.002(2) -0.006(3) C45 0.041(3) 0.065(4) 0.039(3) 0.002(3) -0.007(2) -0.016(3) C46 0.045(3) 0.057(3) 0.036(3) -0.005(2) -0.004(2) -0.009(3) C47 0.044(3) 0.061(4) 0.044(3) 0.002(3) -0.005(2) -0.017(3) C48 0.044(3) 0.069(4) 0.039(3) 0.004(3) -0.005(2) -0.005(3) N1 0.052(3) 0.062(3) 0.039(2) 0.008(2) -0.001(2) -0.003(2) N2 0.058(3) 0.071(3) 0.040(2) 0.011(2) 0.000(2) -0.002(3) N3 0.054(3) 0.044(3) 0.066(3) 0.010(2) -0.007(2) -0.004(2) N4 0.057(3) 0.048(3) 0.066(3) 0.007(2) -0.010(2) -0.008(2) N5 0.056(3) 0.048(3) 0.047(2) 0.001(2) -0.004(2) -0.009(2) N6 0.049(3) 0.066(3) 0.045(2) -0.009(2) 0.002(2) -0.006(3) N7 0.055(3) 0.091(4) 0.040(2) -0.005(3) -0.004(2) 0.002(3) N8 0.058(3) 0.091(4) 0.035(2) -0.006(3) -0.004(2) -0.004(3) N9 0.081(4) 0.057(3) 0.056(3) -0.006(2) 0.003(3) 0.008(3) O1 0.078(3) 0.097(3) 0.047(2) 0.015(2) -0.001(2) -0.010(3) O2 0.075(3) 0.096(4) 0.044(2) -0.009(2) 0.005(2) 0.000(3) O3 0.077(3) 0.075(3) 0.041(2) 0.0052(19) -0.0005(19) -0.007(2) O4 0.082(3) 0.095(3) 0.060(3) 0.015(2) -0.004(2) 0.025(3) O5 0.063(5) 0.094(7) 0.043(4) -0.011(4) 0.004(4) 0.021(5) C50 0.083(11) 0.138(16) 0.167(18) 0.023(14) -0.004(11) -0.066(12) C49 0.38(4) 0.17(2) 0.054(9) -0.022(11) 0.020(17) -0.20(3) O1W 0.142(9) 0.042(5) 0.078(6) -0.011(4) -0.021(6) 0.011(5) O2W 0.138(10) 0.097(8) 0.093(7) -0.001(6) 0.032(7) -0.020(7) O3W 0.099(12) 0.024(7) 0.054(9) 0.011(6) 0.000(8) 0.025(8) O4W 0.137(16) 0.067(11) 0.050(9) 0.002(8) 0.031(10) -0.045(12) O6 0.095(7) 0.054(5) 0.110(7) -0.004(5) -0.013(6) 0.009(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N2 2.089(4) . ? Ag1 N2 2.089(4) 2_666 ? Ag2 N4 2.157(4) . ? Ag2 N5 2.184(4) . ? Ag2 O4 2.530(4) . ? Ag3 N8 2.115(4) . ? Ag3 O2 2.182(4) 1_556 ? C1 C6 1.390(7) . ? C1 C2 1.396(8) . ? C1 N2 1.396(7) . ? C2 C3 1.357(10) . ? C2 H2 0.9300 . ? C3 C4 1.398(10) . ? C3 H3 0.9300 . ? C4 C5 1.381(9) . ? C4 H4 0.9300 . ? C5 C6 1.387(8) . ? C5 H5 0.9300 . ? C6 N1 1.350(7) . ? C7 N2 1.310(7) . ? C7 N1 1.363(7) . ? C7 C8 1.531(9) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N1 1.492(6) . ? C9 C10 1.501(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.493(7) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.512(8) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N3 1.467(7) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.465(9) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 N4 1.327(7) . ? C14 N3 1.373(7) . ? C15 N3 1.388(7) . ? C15 C16 1.392(7) . ? C15 C20 1.404(8) . ? C16 C17 1.381(8) . ? C16 N4 1.399(7) . ? C17 C18 1.399(9) . ? C17 H17 0.9300 . ? C18 C19 1.397(9) . ? C18 H18 0.9300 . ? C19 C20 1.357(9) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 N5 1.320(7) . ? C21 N6 1.344(7) . ? C21 C22 1.470(9) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C28 1.373(8) . ? C23 C24 1.389(7) . ? C23 N5 1.397(7) . ? C24 N6 1.382(8) . ? C24 C25 1.426(8) . ? C25 C26 1.368(10) . ? C25 H25 0.9300 . ? C26 C27 1.389(10) . ? C26 H26 0.9300 . ? C27 C28 1.369(8) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 N6 1.486(7) . ? C29 C30 1.555(8) . ? C30 C31 1.525(9) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.499(8) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 N7 1.482(8) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.462(10) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 N8 1.318(8) . ? C34 N7 1.382(7) . ? C35 C38 1.363(10) . ? C35 N8 1.382(8) . ? C35 C36 1.409(8) . ? C36 N7 1.370(8) . ? C36 C37 1.379(9) . ? C37 C39 1.380(12) . ? C37 H37 0.9300 . ? C38 C40 1.429(11) . ? C38 H38 0.9300 . ? C39 C40 1.400(12) . ? C39 H39 0.9300 . ? C40 H40 0.9300 . ? C41 O1 1.243(7) . ? C41 O2 1.254(7) . ? C41 C43 1.504(7) . ? C42 O3 1.245(6) . ? C42 O4 1.254(7) . ? C42 C45 1.506(8) . ? C43 C48 1.355(8) . ? C43 C44 1.400(7) . ? C44 C45 1.392(7) . ? C44 H44 0.9300 . ? C45 C46 1.378(8) . ? C46 C47 1.392(7) . ? C46 H46 0.9300 . ? C47 N9 1.392(8) . ? C47 C48 1.413(7) . ? C48 H48 0.9300 . ? N9 H9N 0.8600 . ? N9 H9M 0.8600 . ? O2 Ag3 2.182(4) 1_554 ? O5 C49 1.45(3) . ? O5 H5A 0.8200 . ? C50 C49 1.63(3) . ? C50 H50A 0.9600 . ? C50 H50B 0.9600 . ? C50 H50C 0.9600 . ? C49 H49A 0.9700 . ? C49 H49B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ag1 N2 180 . 2_666 ? N4 Ag2 N5 146.96(17) . . ? N4 Ag2 O4 109.06(17) . . ? N5 Ag2 O4 101.72(16) . . ? N8 Ag3 O2 167.63(18) . 1_556 ? C6 C1 C2 120.8(6) . . ? C6 C1 N2 108.0(5) . . ? C2 C1 N2 131.1(5) . . ? C3 C2 C1 117.4(6) . . ? C3 C2 H2 121.3 . . ? C1 C2 H2 121.3 . . ? C2 C3 C4 122.3(6) . . ? C2 C3 H3 118.8 . . ? C4 C3 H3 118.8 . . ? C5 C4 C3 120.5(7) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 117.6(5) . . ? C4 C5 H5 121.2 . . ? C6 C5 H5 121.2 . . ? N1 C6 C5 132.3(5) . . ? N1 C6 C1 106.4(5) . . ? C5 C6 C1 121.2(6) . . ? N2 C7 N1 111.0(6) . . ? N2 C7 C8 124.7(5) . . ? N1 C7 C8 124.3(5) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 C10 112.4(4) . . ? N1 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? N1 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C9 111.0(4) . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10B 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C10 C11 C12 114.0(4) . . ? C10 C11 H11A 108.8 . . ? C12 C11 H11A 108.8 . . ? C10 C11 H11B 108.8 . . ? C12 C11 H11B 108.8 . . ? H11A C11 H11B 107.6 . . ? N3 C12 C11 111.4(4) . . ? N3 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? N3 C12 H12B 109.3 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N4 C14 N3 111.2(5) . . ? N4 C14 C13 123.4(5) . . ? N3 C14 C13 125.4(5) . . ? N3 C15 C16 106.0(5) . . ? N3 C15 C20 132.4(5) . . ? C16 C15 C20 121.6(5) . . ? C17 C16 C15 121.4(5) . . ? C17 C16 N4 129.6(5) . . ? C15 C16 N4 109.0(5) . . ? C16 C17 C18 116.8(6) . . ? C16 C17 H17 121.6 . . ? C18 C17 H17 121.6 . . ? C19 C18 C17 121.2(6) . . ? C19 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C20 C19 C18 122.3(6) . . ? C20 C19 H19 118.8 . . ? C18 C19 H19 118.8 . . ? C19 C20 C15 116.8(5) . . ? C19 C20 H20 121.6 . . ? C15 C20 H20 121.6 . . ? N5 C21 N6 112.3(5) . . ? N5 C21 C22 125.1(5) . . ? N6 C21 C22 122.5(5) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C28 C23 C24 121.9(5) . . ? C28 C23 N5 130.7(5) . . ? C24 C23 N5 107.3(5) . . ? N6 C24 C23 107.1(5) . . ? N6 C24 C25 131.8(6) . . ? C23 C24 C25 121.0(6) . . ? C26 C25 C24 115.1(6) . . ? C26 C25 H25 122.4 . . ? C24 C25 H25 122.4 . . ? C25 C26 C27 123.3(6) . . ? C25 C26 H26 118.4 . . ? C27 C26 H26 118.4 . . ? C28 C27 C26 121.2(7) . . ? C28 C27 H27 119.4 . . ? C26 C27 H27 119.4 . . ? C27 C28 C23 117.5(6) . . ? C27 C28 H28 121.3 . . ? C23 C28 H28 121.3 . . ? N6 C29 C30 111.2(4) . . ? C31 C30 C29 112.6(6) . . ? C31 C30 H30A 109.1 . . ? C29 C30 H30A 109.1 . . ? C31 C30 H30B 109.1 . . ? C29 C30 H30B 109.1 . . ? H30A C30 H30B 107.8 . . ? C32 C31 C30 110.5(6) . . ? C32 C31 H31A 109.6 . . ? C30 C31 H31A 109.6 . . ? C32 C31 H31B 109.6 . . ? C30 C31 H31B 109.6 . . ? H31A C31 H31B 108.1 . . ? N7 C32 C31 113.1(5) . . ? N7 C32 H32A 109.0 . . ? C31 C32 H32A 109.0 . . ? N7 C32 H32B 109.0 . . ? C31 C32 H32B 109.0 . . ? H32A C32 H32B 107.8 . . ? C34 C33 H33A 109.5 . . ? C34 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C34 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? N8 C34 N7 110.3(6) . . ? N8 C34 C33 126.2(6) . . ? N7 C34 C33 123.4(6) . . ? C38 C35 N8 130.0(6) . . ? C38 C35 C36 121.0(6) . . ? N8 C35 C36 109.0(6) . . ? N7 C36 C37 132.2(6) . . ? N7 C36 C35 105.1(5) . . ? C37 C36 C35 122.6(7) . . ? C36 C37 C39 116.8(7) . . ? C36 C37 H37 121.6 . . ? C39 C37 H37 121.6 . . ? C35 C38 C40 117.2(7) . . ? C35 C38 H38 121.4 . . ? C40 C38 H38 121.4 . . ? C37 C39 C40 121.9(7) . . ? C37 C39 H39 119.1 . . ? C40 C39 H39 119.1 . . ? C39 C40 C38 120.5(8) . . ? C39 C40 H40 119.8 . . ? C38 C40 H40 119.8 . . ? O1 C41 O2 122.4(6) . . ? O1 C41 C43 119.6(6) . . ? O2 C41 C43 118.0(5) . . ? O3 C42 O4 122.7(5) . . ? O3 C42 C45 119.0(6) . . ? O4 C42 C45 118.3(5) . . ? C48 C43 C44 119.3(5) . . ? C48 C43 C41 120.5(5) . . ? C44 C43 C41 120.2(5) . . ? C45 C44 C43 119.8(5) . . ? C45 C44 H44 120.1 . . ? C43 C44 H44 120.1 . . ? C46 C45 C44 119.8(5) . . ? C46 C45 C42 119.1(5) . . ? C44 C45 C42 121.1(6) . . ? C45 C46 C47 121.6(5) . . ? C45 C46 H46 119.2 . . ? C47 C46 H46 119.2 . . ? C46 C47 N9 121.7(5) . . ? C46 C47 C48 116.9(6) . . ? N9 C47 C48 121.4(5) . . ? C43 C48 C47 122.5(5) . . ? C43 C48 H48 118.8 . . ? C47 C48 H48 118.8 . . ? C6 N1 C7 108.2(4) . . ? C6 N1 C9 127.6(5) . . ? C7 N1 C9 124.1(5) . . ? C7 N2 C1 106.4(4) . . ? C7 N2 Ag1 124.8(4) . . ? C1 N2 Ag1 128.4(3) . . ? C14 N3 C15 107.4(4) . . ? C14 N3 C12 125.8(5) . . ? C15 N3 C12 126.3(5) . . ? C14 N4 C16 106.4(4) . . ? C14 N4 Ag2 127.2(4) . . ? C16 N4 Ag2 126.4(3) . . ? C21 N5 C23 106.5(4) . . ? C21 N5 Ag2 127.0(4) . . ? C23 N5 Ag2 126.4(4) . . ? C21 N6 C24 106.7(5) . . ? C21 N6 C29 128.7(6) . . ? C24 N6 C29 124.7(5) . . ? C36 N7 C34 108.4(5) . . ? C36 N7 C32 125.5(5) . . ? C34 N7 C32 126.0(6) . . ? C34 N8 C35 107.2(5) . . ? C34 N8 Ag3 129.5(4) . . ? C35 N8 Ag3 122.8(4) . . ? C47 N9 H9N 120.0 . . ? C47 N9 H9M 120.0 . . ? H9N N9 H9M 120.0 . . ? C41 O2 Ag3 107.2(4) . 1_554 ? C42 O4 Ag2 94.6(3) . . ? C49 O5 H5A 109.5 . . ? C49 C50 H50A 109.5 . . ? C49 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C49 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? O5 C49 C50 112.8(13) . . ? O5 C49 H49A 109.0 . . ? C50 C49 H49A 109.0 . . ? O5 C49 H49B 109.0 . . ? C50 C49 H49B 109.0 . . ? H49A C49 H49B 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -2.0(8) . . . . ? N2 C1 C2 C3 179.0(6) . . . . ? C1 C2 C3 C4 1.1(10) . . . . ? C2 C3 C4 C5 -0.8(10) . . . . ? C3 C4 C5 C6 1.3(9) . . . . ? C4 C5 C6 N1 -177.8(6) . . . . ? C4 C5 C6 C1 -2.2(8) . . . . ? C2 C1 C6 N1 179.2(5) . . . . ? N2 C1 C6 N1 -1.6(6) . . . . ? C2 C1 C6 C5 2.6(8) . . . . ? N2 C1 C6 C5 -178.2(5) . . . . ? N1 C9 C10 C11 179.2(5) . . . . ? C9 C10 C11 C12 -167.3(6) . . . . ? C10 C11 C12 N3 -172.5(5) . . . . ? N3 C15 C16 C17 -177.4(5) . . . . ? C20 C15 C16 C17 1.0(8) . . . . ? N3 C15 C16 N4 0.5(6) . . . . ? C20 C15 C16 N4 178.9(5) . . . . ? C15 C16 C17 C18 -0.9(9) . . . . ? N4 C16 C17 C18 -178.3(6) . . . . ? C16 C17 C18 C19 -0.2(9) . . . . ? C17 C18 C19 C20 1.1(10) . . . . ? C18 C19 C20 C15 -0.9(10) . . . . ? N3 C15 C20 C19 177.9(6) . . . . ? C16 C15 C20 C19 -0.1(9) . . . . ? C28 C23 C24 N6 -178.5(4) . . . . ? N5 C23 C24 N6 -0.1(5) . . . . ? C28 C23 C24 C25 -0.7(7) . . . . ? N5 C23 C24 C25 177.8(4) . . . . ? N6 C24 C25 C26 178.4(5) . . . . ? C23 C24 C25 C26 1.2(7) . . . . ? C24 C25 C26 C27 -1.3(8) . . . . ? C25 C26 C27 C28 0.9(9) . . . . ? C26 C27 C28 C23 -0.3(8) . . . . ? C24 C23 C28 C27 0.3(7) . . . . ? N5 C23 C28 C27 -177.8(5) . . . . ? N6 C29 C30 C31 -55.1(7) . . . . ? C29 C30 C31 C32 -168.9(5) . . . . ? C30 C31 C32 N7 -170.4(5) . . . . ? C38 C35 C36 N7 179.5(5) . . . . ? N8 C35 C36 N7 -0.8(6) . . . . ? C38 C35 C36 C37 1.1(9) . . . . ? N8 C35 C36 C37 -179.2(5) . . . . ? N7 C36 C37 C39 -179.3(6) . . . . ? C35 C36 C37 C39 -1.5(9) . . . . ? N8 C35 C38 C40 -179.5(6) . . . . ? C36 C35 C38 C40 0.1(9) . . . . ? C36 C37 C39 C40 0.6(10) . . . . ? C37 C39 C40 C38 0.7(11) . . . . ? C35 C38 C40 C39 -1.0(10) . . . . ? O1 C41 C43 C48 24.3(7) . . . . ? O2 C41 C43 C48 -157.9(5) . . . . ? O1 C41 C43 C44 -154.4(5) . . . . ? O2 C41 C43 C44 23.4(7) . . . . ? C48 C43 C44 C45 -0.4(7) . . . . ? C41 C43 C44 C45 178.3(4) . . . . ? C43 C44 C45 C46 1.7(7) . . . . ? C43 C44 C45 C42 -178.0(4) . . . . ? O3 C42 C45 C46 21.8(7) . . . . ? O4 C42 C45 C46 -158.2(5) . . . . ? O3 C42 C45 C44 -158.5(5) . . . . ? O4 C42 C45 C44 21.6(7) . . . . ? C44 C45 C46 C47 -2.5(7) . . . . ? C42 C45 C46 C47 177.2(4) . . . . ? C45 C46 C47 N9 -175.7(4) . . . . ? C45 C46 C47 C48 2.0(7) . . . . ? C44 C43 C48 C47 -0.1(7) . . . . ? C41 C43 C48 C47 -178.8(5) . . . . ? C46 C47 C48 C43 -0.7(7) . . . . ? N9 C47 C48 C43 177.0(5) . . . . ? C5 C6 N1 C7 177.5(6) . . . . ? C1 C6 N1 C7 1.4(6) . . . . ? C5 C6 N1 C9 -0.2(9) . . . . ? C1 C6 N1 C9 -176.3(5) . . . . ? N2 C7 N1 C6 -0.8(6) . . . . ? C8 C7 N1 C6 -179.8(5) . . . . ? N2 C7 N1 C9 177.0(4) . . . . ? C8 C7 N1 C9 -2.0(8) . . . . ? C10 C9 N1 C6 96.4(7) . . . . ? C10 C9 N1 C7 -80.9(7) . . . . ? N1 C7 N2 C1 -0.3(6) . . . . ? C8 C7 N2 C1 178.8(5) . . . . ? N1 C7 N2 Ag1 -173.1(3) . . . . ? C8 C7 N2 Ag1 6.0(8) . . . . ? C6 C1 N2 C7 1.1(6) . . . . ? C2 C1 N2 C7 -179.8(6) . . . . ? C6 C1 N2 Ag1 173.6(3) . . . . ? C2 C1 N2 Ag1 -7.3(8) . . . . ? N2 Ag1 N2 C7 105(100) 2_666 . . . ? N2 Ag1 N2 C1 -66(100) 2_666 . . . ? N4 C14 N3 C15 1.1(6) . . . . ? C13 C14 N3 C15 179.8(6) . . . . ? N4 C14 N3 C12 173.8(5) . . . . ? C13 C14 N3 C12 -7.6(9) . . . . ? C16 C15 N3 C14 -0.9(6) . . . . ? C20 C15 N3 C14 -179.2(6) . . . . ? C16 C15 N3 C12 -173.5(5) . . . . ? C20 C15 N3 C12 8.2(9) . . . . ? C11 C12 N3 C14 -74.2(8) . . . . ? C11 C12 N3 C15 97.0(7) . . . . ? N3 C14 N4 C16 -0.8(6) . . . . ? C13 C14 N4 C16 -179.5(6) . . . . ? N3 C14 N4 Ag2 177.3(4) . . . . ? C13 C14 N4 Ag2 -1.4(9) . . . . ? C17 C16 N4 C14 177.9(6) . . . . ? C15 C16 N4 C14 0.2(6) . . . . ? C17 C16 N4 Ag2 -0.3(9) . . . . ? C15 C16 N4 Ag2 -178.0(3) . . . . ? N5 Ag2 N4 C14 46.9(7) . . . . ? O4 Ag2 N4 C14 -155.4(5) . . . . ? N5 Ag2 N4 C16 -135.4(4) . . . . ? O4 Ag2 N4 C16 22.4(5) . . . . ? N6 C21 N5 C23 -0.1(6) . . . . ? C22 C21 N5 C23 179.3(6) . . . . ? N6 C21 N5 Ag2 176.7(3) . . . . ? C22 C21 N5 Ag2 -3.8(8) . . . . ? C28 C23 N5 C21 178.4(5) . . . . ? C24 C23 N5 C21 0.1(5) . . . . ? C28 C23 N5 Ag2 1.5(7) . . . . ? C24 C23 N5 Ag2 -176.8(3) . . . . ? N4 Ag2 N5 C21 41.8(6) . . . . ? O4 Ag2 N5 C21 -116.7(4) . . . . ? N4 Ag2 N5 C23 -141.9(4) . . . . ? O4 Ag2 N5 C23 59.6(4) . . . . ? N5 C21 N6 C24 0.1(6) . . . . ? C22 C21 N6 C24 -179.4(5) . . . . ? N5 C21 N6 C29 179.8(4) . . . . ? C22 C21 N6 C29 0.4(9) . . . . ? C23 C24 N6 C21 0.0(5) . . . . ? C25 C24 N6 C21 -177.5(5) . . . . ? C23 C24 N6 C29 -179.8(4) . . . . ? C25 C24 N6 C29 2.7(8) . . . . ? C30 C29 N6 C21 -77.5(7) . . . . ? C30 C29 N6 C24 102.2(6) . . . . ? C37 C36 N7 C34 178.7(6) . . . . ? C35 C36 N7 C34 0.6(6) . . . . ? C37 C36 N7 C32 2.3(9) . . . . ? C35 C36 N7 C32 -175.9(5) . . . . ? N8 C34 N7 C36 -0.2(6) . . . . ? C33 C34 N7 C36 -179.2(5) . . . . ? N8 C34 N7 C32 176.3(5) . . . . ? C33 C34 N7 C32 -2.7(8) . . . . ? C31 C32 N7 C36 -68.6(7) . . . . ? C31 C32 N7 C34 115.5(7) . . . . ? N7 C34 N8 C35 -0.3(6) . . . . ? C33 C34 N8 C35 178.7(5) . . . . ? N7 C34 N8 Ag3 -172.2(3) . . . . ? C33 C34 N8 Ag3 6.8(8) . . . . ? C38 C35 N8 C34 -179.6(6) . . . . ? C36 C35 N8 C34 0.7(6) . . . . ? C38 C35 N8 Ag3 -7.1(8) . . . . ? C36 C35 N8 Ag3 173.2(3) . . . . ? O2 Ag3 N8 C34 117.1(10) 1_556 . . . ? O2 Ag3 N8 C35 -53.7(11) 1_556 . . . ? O1 C41 O2 Ag3 16.5(7) . . . 1_554 ? C43 C41 O2 Ag3 -161.2(4) . . . 1_554 ? O3 C42 O4 Ag2 -8.5(6) . . . . ? C45 C42 O4 Ag2 171.4(4) . . . . ? N4 Ag2 O4 C42 98.2(4) . . . . ? N5 Ag2 O4 C42 -94.0(4) . . . . ? 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 N9 H9N O3 0.86 2.24 3.089(6) 169 2_685 O5 H5A O4 0.82 1.89 2.701(10) 170 1_546 _diffrn_measured_fraction_theta_max 0.838 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.928 _refine_diff_density_min -0.403 _refine_diff_density_rms 0.112 #====end