# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_twin5 _database_code_depnum_ccdc_archive 'CCDC 900359' #TrackingRef '0zn4pinafumarictwinfinal.cif' _audit_update_record ; 2012-08-02 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H11 N3 O5 Zn' _chemical_formula_weight 378.66 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 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 13.596(2) _cell_length_b 14.050(2) _cell_length_c 19.495(3) _cell_angle_alpha 90.00 _cell_angle_beta 125.036(8) _cell_angle_gamma 90.00 _cell_volume 3049.2(8) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.650 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 1.643 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7273 _exptl_absorpt_correction_T_max 0.7744 _exptl_absorpt_process_details twinabs _exptl_special_details ? _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 31772 _diffrn_reflns_av_R_equivalents 0.0875 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.41 _reflns_number_total 5124 _reflns_number_gt 4400 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0420P)^2^+6.4774P] 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 5124 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 0.47923(3) 0.11765(3) 0.44454(2) 0.01584(10) Uani 1 1 d . . . O1 O 0.39726(19) 0.18957(15) 0.33721(12) 0.0298(5) Uani 1 1 d . . . O2 O 0.3755(2) 0.32901(17) 0.38016(13) 0.0393(6) Uani 1 1 d . . . O3 O 0.09035(18) 0.34767(15) 0.06596(12) 0.0274(5) Uani 1 1 d . . . O4 O 0.07020(19) 0.48786(14) 0.11071(14) 0.0333(5) Uani 1 1 d . . . O5 O -0.123(2) 0.0667(14) 0.3223(16) 0.031(2) Uani 0.717(4) 1 d P A 1 O5A O -0.113(6) 0.083(4) 0.327(4) 0.031(2) Uani 0.283(4) 1 d P A 2 N1 N 0.3239(2) 0.1204(2) 0.44681(16) 0.0269(6) Uani 1 1 d . A . N2 N -0.3630(2) 0.10864(18) 0.44269(17) 0.0215(5) Uani 1 1 d . . . N3 N 0.0240(3) 0.1153(3) 0.4568(2) 0.0235(7) Uani 0.717(4) 1 d P A 1 H3 H 0.0410 0.1305 0.5063 0.028 Uiso 0.717(4) 1 calc PR A 1 N3A N -0.0441(9) 0.1132(7) 0.4560(6) 0.0235(7) Uani 0.283(4) 1 d P A 2 H3A H 0.0131 0.1303 0.5075 0.028 Uiso 0.283(4) 1 calc PR A 2 C1 C 0.3526(3) 0.2715(2) 0.32526(18) 0.0240(7) Uani 1 1 d . . . C2 C 0.2627(3) 0.2983(2) 0.23503(17) 0.0232(6) Uani 1 1 d . . . H2 H 0.2455 0.2532 0.1932 0.028 Uiso 1 1 calc R . . C3 C 0.2073(3) 0.3797(2) 0.21110(17) 0.0254(6) Uani 1 1 d . . . H3 H 0.2263 0.4249 0.2533 0.031 Uiso 1 1 calc R . . C4 C 0.1166(3) 0.4071(2) 0.12279(18) 0.0232(7) Uani 1 1 d . . . C5 C 0.2172(3) 0.1028(3) 0.3763(2) 0.0468(10) Uani 1 1 d . . . H5 H 0.2123 0.0925 0.3262 0.056 Uiso 1 1 calc R . . C6 C 0.1131(3) 0.0991(3) 0.3733(3) 0.0578(13) Uani 1 1 d . A . H6 H 0.0383 0.0863 0.3218 0.069 Uiso 1 1 calc R . . C7 C 0.1180(4) 0.1139(3) 0.4447(3) 0.0428(10) Uani 1 1 d . . . C8 C 0.2264(4) 0.1317(3) 0.5159(3) 0.0428(10) Uani 1 1 d . A . H8 H 0.2336 0.1421 0.5667 0.051 Uiso 1 1 calc R . . C9 C 0.3255(3) 0.1350(2) 0.5150(2) 0.0301(8) Uani 1 1 d . . . H9 H 0.4006 0.1484 0.5661 0.036 Uiso 1 1 calc R A . C10 C -0.3816(3) 0.0880(2) 0.3690(2) 0.0331(8) Uani 1 1 d . . . H10 H -0.4619 0.0756 0.3229 0.040 Uiso 1 1 calc R . . C11 C -0.2504(3) 0.1246(2) 0.5061(2) 0.0348(8) Uani 1 1 d . . . H11 H -0.2330 0.1389 0.5597 0.042 Uiso 1 1 calc R . . C12 C -0.2938(3) 0.0835(2) 0.3550(3) 0.0405(9) Uani 1 1 d . A . H12 H -0.3132 0.0687 0.3010 0.049 Uiso 1 1 calc R . . C13 C -0.1560(3) 0.1208(3) 0.4961(3) 0.0495(11) Uani 1 1 d . A . H13 H -0.0758 0.1324 0.5427 0.059 Uiso 1 1 calc R . . C14 C -0.1789(4) 0.1005(2) 0.4198(3) 0.0398(10) Uani 1 1 d . . . C15 C -0.0922(4) 0.0935(3) 0.3932(3) 0.0196(9) Uani 0.717(4) 1 d P A 1 C15A C -0.0306(11) 0.0936(8) 0.3957(7) 0.0196(9) Uani 0.283(4) 1 d P A 2 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 0.01418(17) 0.01928(16) 0.01284(15) 0.00103(16) 0.00705(14) 0.00055(16) O1 0.0308(12) 0.0396(13) 0.0217(11) 0.0132(10) 0.0168(10) 0.0176(11) O2 0.0388(14) 0.0511(15) 0.0159(11) -0.0036(10) 0.0086(11) 0.0081(12) O3 0.0237(12) 0.0387(12) 0.0141(10) 0.0025(9) 0.0076(9) 0.0063(10) O4 0.0282(12) 0.0260(12) 0.0407(13) 0.0145(10) 0.0169(11) 0.0112(10) O5 0.021(4) 0.052(7) 0.020(3) -0.017(4) 0.012(3) -0.015(4) O5A 0.021(4) 0.052(7) 0.020(3) -0.017(4) 0.012(3) -0.015(4) N1 0.0249(15) 0.0338(14) 0.0233(13) 0.0069(13) 0.0146(12) 0.0037(13) N2 0.0141(13) 0.0249(13) 0.0275(13) 0.0067(12) 0.0131(12) 0.0020(11) N3 0.016(2) 0.0330(16) 0.0191(16) -0.0037(15) 0.0088(18) -0.0008(19) N3A 0.016(2) 0.0330(16) 0.0191(16) -0.0037(15) 0.0088(18) -0.0008(19) C1 0.0188(15) 0.0349(18) 0.0170(15) 0.0032(13) 0.0095(13) 0.0026(13) C2 0.0267(17) 0.0263(16) 0.0120(13) -0.0012(12) 0.0084(13) 0.0023(14) C3 0.0288(17) 0.0245(15) 0.0169(14) -0.0028(13) 0.0096(13) 0.0044(14) C4 0.0174(16) 0.0274(17) 0.0243(16) 0.0075(12) 0.0117(14) 0.0030(13) C5 0.0252(19) 0.079(3) 0.036(2) 0.008(2) 0.0177(17) -0.002(2) C6 0.0153(18) 0.075(3) 0.066(3) 0.014(2) 0.0137(19) 0.0004(19) C7 0.047(2) 0.0295(18) 0.086(3) 0.021(2) 0.058(3) 0.0155(19) C8 0.048(2) 0.034(2) 0.072(3) 0.016(2) 0.050(2) 0.0166(19) C9 0.0362(19) 0.0265(18) 0.040(2) 0.0074(14) 0.0295(17) 0.0086(15) C10 0.040(2) 0.0350(19) 0.036(2) 0.0048(16) 0.0288(18) 0.0039(16) C11 0.0214(17) 0.0363(19) 0.040(2) 0.0076(17) 0.0140(15) 0.0019(16) C12 0.046(2) 0.038(2) 0.059(3) 0.0090(18) 0.043(2) 0.0077(18) C13 0.0099(17) 0.037(2) 0.082(3) 0.017(2) 0.0153(19) 0.0026(16) C14 0.054(2) 0.025(2) 0.070(3) 0.0165(18) 0.052(2) 0.0131(17) C15 0.013(2) 0.0240(19) 0.0150(19) -0.0009(14) 0.004(2) -0.0039(19) C15A 0.013(2) 0.0240(19) 0.0150(19) -0.0009(14) 0.004(2) -0.0039(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 O1 1.9909(19) . ? Zn1 O3 2.0044(19) 8_556 ? Zn1 O4 2.026(2) 4_545 ? Zn1 N1 2.138(3) . ? Zn1 N2 2.170(2) 1_655 ? O1 C1 1.259(4) . ? O2 C1 1.230(4) . ? O3 C4 1.264(3) . ? O3 Zn1 2.0043(19) 8_455 ? O4 C4 1.253(3) . ? O4 Zn1 2.026(2) 4 ? O5 C15 1.25(2) . ? O5A C15A 1.16(6) . ? N1 C5 1.329(4) . ? N1 C9 1.332(4) . ? N2 C11 1.322(4) . ? N2 C10 1.340(4) . ? N2 Zn1 2.170(2) 1_455 ? N3 C15 1.370(6) . ? N3 C7 1.428(5) . ? N3 H3 0.8800 . ? N3A C15A 1.319(16) . ? N3A C14 1.550(10) . ? N3A H3A 0.8800 . ? C1 C2 1.504(4) . ? C2 C3 1.300(4) . ? C2 H2 0.9500 . ? C3 C4 1.482(4) . ? C3 H3 0.9500 . ? C5 C6 1.385(5) . ? C5 H5 0.9500 . ? C6 C7 1.371(6) . ? C6 H6 0.9500 . ? C7 C8 1.346(6) . ? C7 C15A 1.692(13) . ? C8 C9 1.359(4) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C12 1.370(4) . ? C10 H10 0.9500 . ? C11 C13 1.406(5) . ? C11 H11 0.9500 . ? C12 C14 1.352(5) . ? C12 H12 0.9500 . ? C13 C14 1.362(6) . ? C13 H13 0.9500 . ? C14 C15 1.541(6) . ? 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 O3 134.87(9) . 8_556 ? O1 Zn1 O4 94.78(9) . 4_545 ? O3 Zn1 O4 129.91(9) 8_556 4_545 ? O1 Zn1 N1 92.81(10) . . ? O3 Zn1 N1 93.15(9) 8_556 . ? O4 Zn1 N1 89.84(10) 4_545 . ? O1 Zn1 N2 88.53(9) . 1_655 ? O3 Zn1 N2 87.23(9) 8_556 1_655 ? O4 Zn1 N2 88.17(10) 4_545 1_655 ? N1 Zn1 N2 177.68(12) . 1_655 ? C1 O1 Zn1 125.30(19) . . ? C4 O3 Zn1 121.09(18) . 8_455 ? C4 O4 Zn1 153.2(2) . 4 ? C5 N1 C9 116.4(3) . . ? C5 N1 Zn1 118.6(2) . . ? C9 N1 Zn1 124.9(2) . . ? C11 N2 C10 116.4(3) . . ? C11 N2 Zn1 126.8(2) . 1_455 ? C10 N2 Zn1 116.8(2) . 1_455 ? C15 N3 C7 121.5(4) . . ? C15 N3 H3 119.2 . . ? C7 N3 H3 119.2 . . ? C15A N3A C14 107.7(9) . . ? C15A N3A H3A 126.2 . . ? C14 N3A H3A 126.2 . . ? O2 C1 O1 125.8(3) . . ? O2 C1 C2 118.9(3) . . ? O1 C1 C2 115.3(3) . . ? C3 C2 C1 123.7(3) . . ? C3 C2 H2 118.2 . . ? C1 C2 H2 118.2 . . ? C2 C3 C4 124.8(3) . . ? C2 C3 H3 117.6 . . ? C4 C3 H3 117.6 . . ? O4 C4 O3 125.1(3) . . ? O4 C4 C3 116.6(3) . . ? O3 C4 C3 118.3(2) . . ? N1 C5 C6 122.2(4) . . ? N1 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C7 C6 C5 119.9(4) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C8 C7 C6 117.5(3) . . ? C8 C7 N3 112.4(4) . . ? C6 C7 N3 130.1(4) . . ? C8 C7 C15A 149.3(5) . . ? C6 C7 C15A 93.1(5) . . ? N3 C7 C15A 37.1(4) . . ? C7 C8 C9 120.0(4) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? N1 C9 C8 124.0(4) . . ? N1 C9 H9 118.0 . . ? C8 C9 H9 118.0 . . ? N2 C10 C12 125.0(4) . . ? N2 C10 H10 117.5 . . ? C12 C10 H10 117.5 . . ? N2 C11 C13 121.5(4) . . ? N2 C11 H11 119.2 . . ? C13 C11 H11 119.2 . . ? C14 C12 C10 118.5(4) . . ? C14 C12 H12 120.8 . . ? C10 C12 H12 120.8 . . ? C14 C13 C11 120.3(4) . . ? C14 C13 H13 119.9 . . ? C11 C13 H13 119.9 . . ? C12 C14 C13 118.4(3) . . ? C12 C14 C15 111.7(4) . . ? C13 C14 C15 129.9(4) . . ? C12 C14 N3A 151.1(5) . . ? C13 C14 N3A 90.5(5) . . ? C15 C14 N3A 39.4(4) . . ? O5 C15 N3 123.5(12) . . ? O5 C15 C14 123.6(11) . . ? N3 C15 C14 112.8(4) . . ? O5A C15A N3A 122(4) . . ? O5A C15A C7 136(4) . . ? N3A C15A C7 101.2(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 O3 Zn1 O1 C1 -38.1(3) 8_556 . . . ? O4 Zn1 O1 C1 149.2(2) 4_545 . . . ? N1 Zn1 O1 C1 59.1(3) . . . . ? N2 Zn1 O1 C1 -122.8(3) 1_655 . . . ? O1 Zn1 N1 C5 43.4(3) . . . . ? O3 Zn1 N1 C5 178.7(3) 8_556 . . . ? O4 Zn1 N1 C5 -51.4(3) 4_545 . . . ? N2 Zn1 N1 C5 -82(3) 1_655 . . . ? O1 Zn1 N1 C9 -139.3(3) . . . . ? O3 Zn1 N1 C9 -4.1(3) 8_556 . . . ? O4 Zn1 N1 C9 125.9(3) 4_545 . . . ? N2 Zn1 N1 C9 95(3) 1_655 . . . ? Zn1 O1 C1 O2 18.2(4) . . . . ? Zn1 O1 C1 C2 -161.17(19) . . . . ? O2 C1 C2 C3 0.2(5) . . . . ? O1 C1 C2 C3 179.6(3) . . . . ? C1 C2 C3 C4 -178.7(3) . . . . ? Zn1 O4 C4 O3 -52.5(6) 4 . . . ? Zn1 O4 C4 C3 128.9(4) 4 . . . ? Zn1 O3 C4 O4 6.6(4) 8_455 . . . ? Zn1 O3 C4 C3 -174.8(2) 8_455 . . . ? C2 C3 C4 O4 178.8(3) . . . . ? C2 C3 C4 O3 0.1(5) . . . . ? C9 N1 C5 C6 -0.4(6) . . . . ? Zn1 N1 C5 C6 177.1(3) . . . . ? N1 C5 C6 C7 0.1(7) . . . . ? C5 C6 C7 C8 0.0(6) . . . . ? C5 C6 C7 N3 178.7(4) . . . . ? C5 C6 C7 C15A -177.3(5) . . . . ? C15 N3 C7 C8 -176.3(4) . . . . ? C15 N3 C7 C6 5.0(7) . . . . ? C15 N3 C7 C15A -1.6(7) . . . . ? C6 C7 C8 C9 0.3(6) . . . . ? N3 C7 C8 C9 -178.7(3) . . . . ? C15A C7 C8 C9 175.1(8) . . . . ? C5 N1 C9 C8 0.7(5) . . . . ? Zn1 N1 C9 C8 -176.6(3) . . . . ? C7 C8 C9 N1 -0.7(6) . . . . ? C11 N2 C10 C12 -0.8(5) . . . . ? Zn1 N2 C10 C12 177.0(3) 1_455 . . . ? C10 N2 C11 C13 0.6(5) . . . . ? Zn1 N2 C11 C13 -177.0(3) 1_455 . . . ? N2 C10 C12 C14 0.3(5) . . . . ? N2 C11 C13 C14 0.1(6) . . . . ? C10 C12 C14 C13 0.4(5) . . . . ? C10 C12 C14 C15 -179.5(3) . . . . ? C10 C12 C14 N3A -176.2(9) . . . . ? C11 C13 C14 C12 -0.6(6) . . . . ? C11 C13 C14 C15 179.3(3) . . . . ? C11 C13 C14 N3A 177.8(5) . . . . ? C15A N3A C14 C12 -5.6(15) . . . . ? C15A N3A C14 C13 177.3(8) . . . . ? C15A N3A C14 C15 -0.8(6) . . . . ? C7 N3 C15 O5 3.6(14) . . . . ? C7 N3 C15 C14 -179.4(4) . . . . ? C12 C14 C15 O5 -6.2(14) . . . . ? C13 C14 C15 O5 174.0(13) . . . . ? N3A C14 C15 O5 176.3(15) . . . . ? C12 C14 C15 N3 176.9(4) . . . . ? C13 C14 C15 N3 -3.0(6) . . . . ? N3A C14 C15 N3 -0.6(7) . . . . ? C14 N3A C15A O5A 10(4) . . . . ? C14 N3A C15A C7 178.5(6) . . . . ? C8 C7 C15A O5A 176(4) . . . . ? C6 C7 C15A O5A -9(5) . . . . ? N3 C7 C15A O5A 166(5) . . . . ? C8 C7 C15A N3A 9.6(14) . . . . ? C6 C7 C15A N3A -175.0(7) . . . . ? N3 C7 C15A N3A 0.0(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3 O2 0.88 1.90 2.755(4) 162.4 7_556 N3A H3A O2 0.88 1.90 2.777(10) 174.4 7_556 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.473 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.073 data_c2c _database_code_depnum_ccdc_archive 'CCDC 900360' #TrackingRef '0znfum3pinafinal.cif' _audit_update_record ; 2012-08-13 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H14 N3 O6.50 Zn' _chemical_formula_weight 405.66 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 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 18.365(3) _cell_length_b 10.5691(18) _cell_length_c 17.065(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.028(7) _cell_angle_gamma 90.00 _cell_volume 3183.5(9) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 583 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 25.28 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.693 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1656 _exptl_absorpt_coefficient_mu 1.586 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7030 _exptl_absorpt_correction_T_max 0.8180 _exptl_absorpt_process_details SADABS _exptl_special_details ? _diffrn_ambient_temperature 173(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12686 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 25.39 _reflns_number_total 2915 _reflns_number_gt 2518 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0511P)^2^+0.4618P] 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 2915 _refine_ls_number_parameters 241 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0825 _refine_ls_wR_factor_gt 0.0800 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 0.211056(14) 0.02814(3) 0.177057(15) 0.01837(11) Uani 1 1 d . . . O1 O 0.57535(11) -0.06482(18) 0.42986(13) 0.0429(5) Uani 1 1 d . . . O1W O -0.01419(13) -0.1085(2) 0.07293(16) 0.0547(7) Uani 1 1 d D . . H1WA H 0.0309(12) -0.113(3) 0.068(2) 0.066 Uiso 1 1 d D . . H1WB H -0.0380(16) -0.044(2) 0.049(2) 0.066 Uiso 1 1 d D . . O2 O 0.23140(9) -0.11224(15) 0.11212(10) 0.0250(4) Uani 1 1 d . . . O2W O -0.0407(4) -0.2371(7) 0.2241(5) 0.121(3) Uani 0.50 1 d P . . O3 O 0.10905(10) 0.00551(19) 0.19062(12) 0.0381(5) Uani 1 1 d . . . O4 O 0.15909(10) 0.14164(19) 0.28744(11) 0.0361(5) Uani 1 1 d . . . O5 O 0.13266(10) -0.06368(18) 0.00785(11) 0.0339(4) Uani 1 1 d . . . N1 N 0.31269(11) 0.02723(17) 0.26450(12) 0.0190(4) Uani 1 1 d . . . N2 N 0.56376(10) 0.13974(19) 0.46521(12) 0.0234(5) Uani 1 1 d . . . H2N H 0.5319 0.2037 0.4569 0.028 Uiso 1 1 calc R . . N3 N 0.70945(10) 0.30292(18) 0.61863(11) 0.0191(4) Uani 1 1 d . . . C1 C 0.33318(13) 0.1185(2) 0.32108(14) 0.0213(5) Uani 1 1 d . . . H1 H 0.2966 0.1800 0.3250 0.026 Uiso 1 1 calc R . . C2 C 0.40483(13) 0.1267(2) 0.37355(15) 0.0232(5) Uani 1 1 d . . . H2 H 0.4176 0.1936 0.4121 0.028 Uiso 1 1 calc R . . C3 C 0.45823(13) 0.0362(2) 0.36958(14) 0.0206(5) Uani 1 1 d . . . C4 C 0.43604(14) -0.0607(2) 0.31301(15) 0.0243(5) Uani 1 1 d . . . H4 H 0.4707 -0.1261 0.3101 0.029 Uiso 1 1 calc R . . C5 C 0.36407(13) -0.0617(2) 0.26148(15) 0.0231(5) Uani 1 1 d . . . H5 H 0.3501 -0.1276 0.2223 0.028 Uiso 1 1 calc R . . C6 C 0.64378(12) 0.2688(2) 0.56690(14) 0.0211(5) Uani 1 1 d . . . H6 H 0.6008 0.3213 0.5621 0.025 Uiso 1 1 calc R . . C7 C 0.63536(12) 0.1605(2) 0.51996(14) 0.0195(5) Uani 1 1 d . . . C8 C 0.69766(13) 0.0817(2) 0.52857(15) 0.0235(5) Uani 1 1 d . . . H8 H 0.6940 0.0060 0.4977 0.028 Uiso 1 1 calc R . . C9 C 0.76534(13) 0.1170(2) 0.58357(15) 0.0252(5) Uani 1 1 d . . . H9 H 0.8087 0.0644 0.5914 0.030 Uiso 1 1 calc R . . C10 C 0.76993(13) 0.2276(2) 0.62666(14) 0.0224(5) Uani 1 1 d . . . H10 H 0.8171 0.2515 0.6631 0.027 Uiso 1 1 calc R . . C11 C 0.53856(14) 0.0320(2) 0.42389(15) 0.0235(5) Uani 1 1 d . . . C12 C 0.10551(14) 0.0772(3) 0.24991(15) 0.0264(6) Uani 1 1 d . . . C13 C 0.03379(14) 0.0777(3) 0.27417(17) 0.0378(7) Uani 1 1 d . . . H13 H 0.0383 0.0781 0.3310 0.045 Uiso 1 1 calc R . . C14 C 0.21725(13) -0.2201(2) -0.01233(14) 0.0214(5) Uani 1 1 d . . . H14 H 0.1854 -0.2382 -0.0653 0.026 Uiso 1 1 calc R . . C15 C 0.19058(13) -0.1255(2) 0.03850(14) 0.0209(5) 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 0.01469(16) 0.02117(18) 0.01832(17) 0.00003(11) 0.00302(11) -0.00071(10) O1 0.0298(10) 0.0320(11) 0.0531(13) -0.0146(10) -0.0113(9) 0.0105(9) O1W 0.0452(13) 0.0299(12) 0.0716(17) -0.0036(11) -0.0131(12) -0.0021(10) O2 0.0281(9) 0.0262(9) 0.0190(9) -0.0048(7) 0.0035(7) 0.0006(7) O2W 0.129(6) 0.103(5) 0.141(7) -0.001(5) 0.051(5) -0.011(4) O3 0.0238(10) 0.0523(12) 0.0413(12) -0.0181(10) 0.0143(9) -0.0127(9) O4 0.0270(10) 0.0449(12) 0.0364(11) -0.0077(9) 0.0086(8) -0.0053(9) O5 0.0323(11) 0.0332(10) 0.0322(11) -0.0024(8) 0.0023(8) 0.0078(8) N1 0.0187(10) 0.0209(11) 0.0172(10) -0.0005(8) 0.0046(8) 0.0001(8) N2 0.0156(10) 0.0215(11) 0.0286(11) -0.0044(9) -0.0011(8) 0.0040(8) N3 0.0172(9) 0.0213(10) 0.0177(10) 0.0005(8) 0.0032(8) -0.0001(8) C1 0.0191(12) 0.0223(13) 0.0226(13) -0.0039(10) 0.0059(10) 0.0022(10) C2 0.0213(12) 0.0242(13) 0.0231(13) -0.0076(10) 0.0044(10) 0.0002(10) C3 0.0186(12) 0.0230(13) 0.0187(12) 0.0005(10) 0.0026(10) -0.0007(10) C4 0.0227(13) 0.0232(13) 0.0249(13) -0.0033(10) 0.0029(10) 0.0048(10) C5 0.0234(13) 0.0210(12) 0.0239(13) -0.0059(10) 0.0050(10) 0.0007(10) C6 0.0155(11) 0.0225(13) 0.0253(13) 0.0008(10) 0.0055(10) 0.0013(9) C7 0.0168(11) 0.0228(12) 0.0178(12) 0.0011(10) 0.0031(9) -0.0003(10) C8 0.0220(12) 0.0223(13) 0.0250(13) -0.0032(11) 0.0044(10) 0.0018(10) C9 0.0181(12) 0.0290(14) 0.0260(13) 0.0002(11) 0.0023(10) 0.0058(10) C10 0.0171(11) 0.0268(13) 0.0218(13) 0.0017(10) 0.0025(10) 0.0004(10) C11 0.0207(13) 0.0259(14) 0.0221(13) -0.0034(10) 0.0031(10) 0.0022(10) C12 0.0225(13) 0.0310(14) 0.0251(14) 0.0033(11) 0.0057(11) 0.0011(11) C13 0.0266(13) 0.062(2) 0.0267(15) 0.0042(14) 0.0111(11) 0.0015(14) C14 0.0251(12) 0.0203(12) 0.0169(12) -0.0007(9) 0.0030(10) -0.0061(9) C15 0.0229(12) 0.0189(12) 0.0210(12) 0.0021(10) 0.0062(10) -0.0047(10) _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 1.9488(16) . ? Zn1 O3 1.9646(18) . ? Zn1 N3 2.0412(19) 8_455 ? Zn1 N1 2.043(2) . ? O1 C11 1.215(3) . ? O1W H1WA 0.853(17) . ? O1W H1WB 0.855(17) . ? O2 C15 1.281(3) . ? O2W O2W 1.511(14) 2 ? O3 C12 1.280(3) . ? O4 C12 1.223(3) . ? O5 C15 1.235(3) . ? N1 C1 1.343(3) . ? N1 C5 1.343(3) . ? N2 C11 1.352(3) . ? N2 C7 1.404(3) . ? N2 H2N 0.8800 . ? N3 C6 1.333(3) . ? N3 C10 1.343(3) . ? N3 Zn1 2.0412(19) 8_556 ? C1 C2 1.375(3) . ? C1 H1 0.9500 . ? C2 C3 1.385(3) . ? C2 H2 0.9500 . ? C3 C4 1.389(3) . ? C3 C11 1.511(3) . ? C4 C5 1.370(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.381(3) . ? C6 H6 0.9500 . ? C7 C8 1.390(3) . ? C8 C9 1.386(3) . ? C8 H8 0.9500 . ? C9 C10 1.371(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C12 C13 1.486(4) . ? C13 C13 1.287(5) 2 ? C13 H13 0.9500 . ? C14 C14 1.321(5) 7_545 ? C14 C15 1.492(3) . ? C14 H14 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Zn1 O3 108.24(7) . . ? O2 Zn1 N3 111.56(7) . 8_455 ? O3 Zn1 N3 106.17(8) . 8_455 ? O2 Zn1 N1 97.57(7) . . ? O3 Zn1 N1 128.46(8) . . ? N3 Zn1 N1 104.36(7) 8_455 . ? H1WA O1W H1WB 113(3) . . ? C15 O2 Zn1 119.27(15) . . ? C12 O3 Zn1 106.22(15) . . ? C1 N1 C5 118.0(2) . . ? C1 N1 Zn1 122.68(15) . . ? C5 N1 Zn1 119.02(15) . . ? C11 N2 C7 127.0(2) . . ? C11 N2 H2N 116.5 . . ? C7 N2 H2N 116.5 . . ? C6 N3 C10 118.6(2) . . ? C6 N3 Zn1 116.68(15) . 8_556 ? C10 N3 Zn1 124.68(15) . 8_556 ? N1 C1 C2 122.8(2) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C1 C2 C3 119.2(2) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C2 C3 C4 117.9(2) . . ? C2 C3 C11 125.1(2) . . ? C4 C3 C11 117.0(2) . . ? C5 C4 C3 119.9(2) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N1 C5 C4 122.2(2) . . ? N1 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? N3 C6 C7 123.0(2) . . ? N3 C6 H6 118.5 . . ? C7 C6 H6 118.5 . . ? C6 C7 C8 118.6(2) . . ? C6 C7 N2 116.7(2) . . ? C8 C7 N2 124.7(2) . . ? C9 C8 C7 117.9(2) . . ? C9 C8 H8 121.0 . . ? C7 C8 H8 121.0 . . ? C10 C9 C8 120.2(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? N3 C10 C9 121.6(2) . . ? N3 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? O1 C11 N2 124.3(2) . . ? O1 C11 C3 120.2(2) . . ? N2 C11 C3 115.5(2) . . ? O4 C12 O3 122.3(2) . . ? O4 C12 C13 119.9(2) . . ? O3 C12 C13 117.7(2) . . ? C13 C13 C12 126.4(3) 2 . ? C13 C13 H13 116.8 2 . ? C12 C13 H13 116.8 . . ? C14 C14 C15 123.5(3) 7_545 . ? C14 C14 H14 118.3 7_545 . ? C15 C14 H14 118.3 . . ? O5 C15 O2 124.1(2) . . ? O5 C15 C14 119.4(2) . . ? O2 C15 C14 116.5(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 O3 Zn1 O2 C15 63.49(18) . . . . ? N3 Zn1 O2 C15 -52.96(18) 8_455 . . . ? N1 Zn1 O2 C15 -161.72(17) . . . . ? O2 Zn1 O3 C12 163.04(16) . . . . ? N3 Zn1 O3 C12 -77.07(18) 8_455 . . . ? N1 Zn1 O3 C12 47.0(2) . . . . ? O2 Zn1 N1 C1 171.33(18) . . . . ? O3 Zn1 N1 C1 -68.1(2) . . . . ? N3 Zn1 N1 C1 56.70(19) 8_455 . . . ? O2 Zn1 N1 C5 -2.69(18) . . . . ? O3 Zn1 N1 C5 117.90(18) . . . . ? N3 Zn1 N1 C5 -117.32(18) 8_455 . . . ? C5 N1 C1 C2 2.3(3) . . . . ? Zn1 N1 C1 C2 -171.75(18) . . . . ? N1 C1 C2 C3 -1.3(4) . . . . ? C1 C2 C3 C4 -1.1(4) . . . . ? C1 C2 C3 C11 -179.1(2) . . . . ? C2 C3 C4 C5 2.4(4) . . . . ? C11 C3 C4 C5 -179.4(2) . . . . ? C1 N1 C5 C4 -1.0(4) . . . . ? Zn1 N1 C5 C4 173.34(19) . . . . ? C3 C4 C5 N1 -1.4(4) . . . . ? C10 N3 C6 C7 -1.2(3) . . . . ? Zn1 N3 C6 C7 176.44(18) 8_556 . . . ? N3 C6 C7 C8 1.7(4) . . . . ? N3 C6 C7 N2 -176.9(2) . . . . ? C11 N2 C7 C6 -167.8(2) . . . . ? C11 N2 C7 C8 13.6(4) . . . . ? C6 C7 C8 C9 -0.6(3) . . . . ? N2 C7 C8 C9 178.0(2) . . . . ? C7 C8 C9 C10 -1.0(4) . . . . ? C6 N3 C10 C9 -0.5(3) . . . . ? Zn1 N3 C10 C9 -177.93(18) 8_556 . . . ? C8 C9 C10 N3 1.6(4) . . . . ? C7 N2 C11 O1 1.2(4) . . . . ? C7 N2 C11 C3 179.3(2) . . . . ? C2 C3 C11 O1 162.2(3) . . . . ? C4 C3 C11 O1 -15.8(4) . . . . ? C2 C3 C11 N2 -15.9(4) . . . . ? C4 C3 C11 N2 166.0(2) . . . . ? Zn1 O3 C12 O4 -1.1(3) . . . . ? Zn1 O3 C12 C13 -179.42(19) . . . . ? O4 C12 C13 C13 139.96(19) . . . 2 ? O3 C12 C13 C13 -41.6(3) . . . 2 ? Zn1 O2 C15 O5 -8.9(3) . . . . ? Zn1 O2 C15 C14 169.56(14) . . . . ? C14 C14 C15 O5 172.1(3) 7_545 . . . ? C14 C14 C15 O2 -6.4(4) 7_545 . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O5 0.853(17) 2.43(2) 3.223(3) 155(3) . O1W H1WB O5 0.855(17) 2.077(19) 2.879(3) 156(3) 5 N2 H2N O1W 0.88 2.05 2.829(3) 146.7 4 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.736 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.068 data_p21c _database_code_depnum_ccdc_archive 'CCDC 900361' #TrackingRef '0znfumarate4pnafinal.cif' _audit_update_record ; 2012-08-15 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H11 N3 O5 Zn' _chemical_formula_weight 378.64 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 P2(1)/c 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 7.8778(15) _cell_length_b 23.005(4) _cell_length_c 8.2756(15) _cell_angle_alpha 90.00 _cell_angle_beta 107.346(2) _cell_angle_gamma 90.00 _cell_volume 1431.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3204 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 25.35 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.757 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 1.749 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5312 _exptl_absorpt_correction_T_max 0.8255 _exptl_absorpt_process_details TWINABS _exptl_special_details ? _diffrn_ambient_temperature 173(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19815 _diffrn_reflns_av_R_equivalents 0.0628 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.40 _reflns_number_total 2639 _reflns_number_gt 2055 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+2.3211P] 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 2639 _refine_ls_number_parameters 220 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 0.02366(6) 0.585289(18) 0.17777(5) 0.01854(15) Uani 1 1 d . . . O1 O 0.3181(4) 0.60996(12) 0.3758(3) 0.0252(6) Uani 1 1 d . . . O2 O 0.1863(3) 0.52507(12) 0.3188(3) 0.0276(7) Uani 1 1 d . . . O3 O -0.1849(3) 0.53496(11) 0.0946(3) 0.0242(6) Uani 1 1 d . . . O4 O -0.3179(4) 0.59729(11) -0.1108(4) 0.0277(7) Uani 1 1 d . . . O5 O -0.5899(4) 0.73595(13) 0.5001(4) 0.0337(7) Uani 1 1 d . . . N1 N -0.0884(4) 0.65148(14) 0.2774(4) 0.0221(7) Uani 1 1 d . . . N2 N -0.4044(4) 0.78435(14) 0.3805(4) 0.0244(8) Uani 1 1 d D . . H2N H -0.374(5) 0.8200(11) 0.354(5) 0.029 Uiso 1 1 d D . . N3 N -0.8818(4) 0.88706(13) 0.4879(4) 0.0186(7) Uani 1 1 d . . . C1 C -0.0447(5) 0.70760(18) 0.2765(5) 0.0264(9) Uani 1 1 d . . . H1 H 0.0605 0.7173 0.2488 0.032 Uiso 1 1 calc R . . C2 C -0.1441(6) 0.75241(17) 0.3139(5) 0.0289(10) Uani 1 1 d . . . H2 H -0.1087 0.7917 0.3090 0.035 Uiso 1 1 calc R . . C3 C -0.2963(5) 0.73924(17) 0.3586(4) 0.0206(8) Uani 1 1 d . . . C4 C -0.3380(5) 0.68060(17) 0.3694(5) 0.0243(9) Uani 1 1 d . . . H4 H -0.4361 0.6694 0.4069 0.029 Uiso 1 1 calc R . . C5 C -0.2343(5) 0.63959(17) 0.3246(5) 0.0242(9) Uani 1 1 d . . . H5 H -0.2675 0.6000 0.3269 0.029 Uiso 1 1 calc R . . C6 C -0.8693(5) 0.89670(18) 0.2046(5) 0.0250(9) Uani 1 1 d . . . H6 H -0.9109 0.9150 0.0971 0.030 Uiso 1 1 calc R . . C7 C -0.6794(5) 0.82910(16) 0.3923(5) 0.0215(8) Uani 1 1 d . . . C8 C -0.7371(5) 0.85487(17) 0.2331(5) 0.0251(9) Uani 1 1 d . . . H8 H -0.6871 0.8441 0.1462 0.030 Uiso 1 1 calc R . . C9 C -0.7549(5) 0.84661(17) 0.5146(5) 0.0212(8) Uani 1 1 d . . . H9 H -0.7146 0.8290 0.6233 0.025 Uiso 1 1 calc R . . C10 C -0.9401(5) 0.91165(16) 0.3317(5) 0.0220(8) Uani 1 1 d . . . H10 H -1.0322 0.9399 0.3099 0.026 Uiso 1 1 calc R . . C11 C -0.5532(5) 0.77904(17) 0.4316(5) 0.0224(9) Uani 1 1 d . . . C12 C 0.3204(5) 0.55650(17) 0.3914(5) 0.0200(8) Uani 1 1 d . . . C13 C 0.4860(5) 0.52832(17) 0.4997(5) 0.0234(9) Uani 1 1 d . . . H13 H 0.5755 0.5522 0.5715 0.028 Uiso 1 1 calc R . . C14 C -0.3186(5) 0.55359(17) -0.0241(5) 0.0212(9) Uani 1 1 d . . . C15 C -0.4865(5) 0.51963(16) -0.0532(5) 0.0211(8) Uani 1 1 d . . . H15 H -0.5798 0.5267 -0.1545 0.025 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0140(2) 0.0201(3) 0.0214(2) 0.00180(19) 0.00501(16) 0.00010(19) O1 0.0237(16) 0.0239(16) 0.0258(15) 0.0016(12) 0.0044(12) 0.0008(12) O2 0.0176(15) 0.0261(16) 0.0337(16) -0.0007(12) -0.0009(12) -0.0005(12) O3 0.0130(14) 0.0266(15) 0.0295(15) 0.0048(12) 0.0010(12) -0.0036(11) O4 0.0230(16) 0.0232(16) 0.0375(17) 0.0083(13) 0.0098(13) -0.0002(12) O5 0.0362(19) 0.0261(16) 0.0472(18) 0.0080(14) 0.0254(15) 0.0051(14) N1 0.0171(17) 0.0253(19) 0.0232(17) 0.0000(14) 0.0050(13) -0.0001(14) N2 0.0243(19) 0.0199(18) 0.0312(19) 0.0003(15) 0.0114(15) -0.0021(15) N3 0.0117(16) 0.0206(17) 0.0224(17) -0.0009(13) 0.0036(13) 0.0024(13) C1 0.019(2) 0.032(2) 0.030(2) -0.0015(18) 0.0088(17) -0.0025(18) C2 0.030(3) 0.020(2) 0.039(2) -0.0035(18) 0.0130(19) -0.0041(17) C3 0.019(2) 0.024(2) 0.0169(18) -0.0036(16) 0.0017(15) 0.0011(17) C4 0.023(2) 0.023(2) 0.031(2) 0.0016(17) 0.0137(18) 0.0014(17) C5 0.023(2) 0.021(2) 0.032(2) 0.0044(17) 0.0124(18) -0.0021(17) C6 0.025(2) 0.030(2) 0.020(2) 0.0027(17) 0.0072(17) -0.0022(18) C7 0.020(2) 0.019(2) 0.027(2) -0.0029(16) 0.0093(17) -0.0006(16) C8 0.027(2) 0.028(2) 0.022(2) -0.0035(17) 0.0099(17) -0.0001(18) C9 0.017(2) 0.024(2) 0.022(2) 0.0001(16) 0.0057(16) 0.0000(17) C10 0.0149(19) 0.018(2) 0.031(2) 0.0018(17) 0.0029(16) 0.0000(16) C11 0.027(2) 0.021(2) 0.020(2) -0.0024(16) 0.0080(17) 0.0013(17) C12 0.017(2) 0.026(2) 0.0172(19) -0.0016(16) 0.0064(16) 0.0011(17) C13 0.018(2) 0.031(2) 0.0180(19) -0.0013(17) 0.0014(16) 0.0005(18) C14 0.018(2) 0.022(2) 0.023(2) -0.0027(17) 0.0055(17) 0.0020(16) C15 0.0125(19) 0.027(2) 0.022(2) 0.0017(16) 0.0031(15) -0.0003(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 1.959(3) . ? Zn1 O2 2.008(3) . ? Zn1 N3 2.031(3) 4_675 ? Zn1 N1 2.052(3) . ? Zn1 O1 2.474(3) . ? Zn1 C12 2.562(4) . ? O1 C12 1.236(5) . ? O2 C12 1.273(4) . ? O3 C14 1.281(4) . ? O4 C14 1.236(4) . ? O5 C11 1.219(5) . ? N1 C1 1.337(5) . ? N1 C5 1.347(5) . ? N2 C11 1.365(5) . ? N2 C3 1.388(5) . ? N2 H2N 0.899(19) . ? N3 C9 1.335(5) . ? N3 C10 1.360(5) . ? N3 Zn1 2.031(3) 4_476 ? C1 C2 1.384(6) . ? C1 H1 0.9500 . ? C2 C3 1.390(5) . ? C2 H2 0.9500 . ? C3 C4 1.398(5) . ? C4 C5 1.370(5) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C10 1.373(5) . ? C6 C8 1.385(6) . ? C6 H6 0.9500 . ? C7 C9 1.378(5) . ? C7 C8 1.391(5) . ? C7 C11 1.493(5) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C12 C13 1.493(5) . ? C13 C13 1.321(8) 3_666 ? C13 H13 0.9500 . ? C14 C15 1.492(5) . ? C15 C15 1.322(7) 3_465 ? C15 H15 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 O2 96.86(11) . . ? O3 Zn1 N3 112.08(12) . 4_675 ? O2 Zn1 N3 110.37(12) . 4_675 ? O3 Zn1 N1 99.41(12) . . ? O2 Zn1 N1 123.69(12) . . ? N3 Zn1 N1 112.29(12) 4_675 . ? O3 Zn1 O1 152.93(10) . . ? O2 Zn1 O1 57.54(10) . . ? N3 Zn1 O1 87.31(11) 4_675 . ? N1 Zn1 O1 89.67(11) . . ? O3 Zn1 C12 125.91(12) . . ? O2 Zn1 C12 29.27(11) . . ? N3 Zn1 C12 98.35(12) 4_675 . ? N1 Zn1 C12 109.13(12) . . ? O1 Zn1 C12 28.34(10) . . ? C12 O1 Zn1 79.8(2) . . ? C12 O2 Zn1 100.3(2) . . ? C14 O3 Zn1 118.9(2) . . ? C1 N1 C5 116.2(3) . . ? C1 N1 Zn1 124.9(3) . . ? C5 N1 Zn1 118.2(3) . . ? C11 N2 C3 126.2(3) . . ? C11 N2 H2N 118(3) . . ? C3 N2 H2N 116(3) . . ? C9 N3 C10 118.1(3) . . ? C9 N3 Zn1 121.3(2) . 4_476 ? C10 N3 Zn1 120.5(2) . 4_476 ? N1 C1 C2 123.7(4) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C1 C2 C3 119.2(4) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? N2 C3 C2 118.9(4) . . ? N2 C3 C4 123.3(4) . . ? C2 C3 C4 117.7(4) . . ? C5 C4 C3 118.5(4) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? N1 C5 C4 124.6(4) . . ? N1 C5 H5 117.7 . . ? C4 C5 H5 117.7 . . ? C10 C6 C8 120.0(4) . . ? C10 C6 H6 120.0 . . ? C8 C6 H6 120.0 . . ? C9 C7 C8 118.7(4) . . ? C9 C7 C11 118.1(3) . . ? C8 C7 C11 122.9(3) . . ? C6 C8 C7 118.3(4) . . ? C6 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? N3 C9 C7 123.2(4) . . ? N3 C9 H9 118.4 . . ? C7 C9 H9 118.4 . . ? N3 C10 C6 121.7(4) . . ? N3 C10 H10 119.2 . . ? C6 C10 H10 119.2 . . ? O5 C11 N2 124.2(4) . . ? O5 C11 C7 119.6(4) . . ? N2 C11 C7 116.2(3) . . ? O1 C12 O2 122.1(4) . . ? O1 C12 C13 118.5(3) . . ? O2 C12 C13 119.4(3) . . ? O1 C12 Zn1 71.9(2) . . ? O2 C12 Zn1 50.46(18) . . ? C13 C12 Zn1 168.8(3) . . ? C13 C13 C12 123.1(5) 3_666 . ? C13 C13 H13 118.5 3_666 . ? C12 C13 H13 118.5 . . ? O4 C14 O3 124.9(4) . . ? O4 C14 C15 119.3(3) . . ? O3 C14 C15 115.8(3) . . ? C15 C15 C14 124.1(5) 3_465 . ? C15 C15 H15 117.9 3_465 . ? C14 C15 H15 117.9 . . ? 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 O3 Zn1 O1 C12 24.2(3) . . . . ? O2 Zn1 O1 C12 3.1(2) . . . . ? N3 Zn1 O1 C12 -113.2(2) 4_675 . . . ? N1 Zn1 O1 C12 134.5(2) . . . . ? O3 Zn1 O2 C12 -173.6(2) . . . . ? N3 Zn1 O2 C12 69.8(2) 4_675 . . . ? N1 Zn1 O2 C12 -67.4(3) . . . . ? O1 Zn1 O2 C12 -3.0(2) . . . . ? O2 Zn1 O3 C14 -169.7(3) . . . . ? N3 Zn1 O3 C14 -54.4(3) 4_675 . . . ? N1 Zn1 O3 C14 64.4(3) . . . . ? O1 Zn1 O3 C14 172.6(2) . . . . ? C12 Zn1 O3 C14 -173.5(2) . . . . ? O3 Zn1 N1 C1 -145.4(3) . . . . ? O2 Zn1 N1 C1 109.8(3) . . . . ? N3 Zn1 N1 C1 -26.7(3) 4_675 . . . ? O1 Zn1 N1 C1 60.3(3) . . . . ? C12 Zn1 N1 C1 81.3(3) . . . . ? O3 Zn1 N1 C5 24.1(3) . . . . ? O2 Zn1 N1 C5 -80.7(3) . . . . ? N3 Zn1 N1 C5 142.8(3) 4_675 . . . ? O1 Zn1 N1 C5 -130.2(3) . . . . ? C12 Zn1 N1 C5 -109.2(3) . . . . ? C5 N1 C1 C2 -2.8(6) . . . . ? Zn1 N1 C1 C2 166.9(3) . . . . ? N1 C1 C2 C3 1.4(6) . . . . ? C11 N2 C3 C2 -176.8(4) . . . . ? C11 N2 C3 C4 7.1(6) . . . . ? C1 C2 C3 N2 -174.1(4) . . . . ? C1 C2 C3 C4 2.2(6) . . . . ? N2 C3 C4 C5 171.8(4) . . . . ? C2 C3 C4 C5 -4.3(6) . . . . ? C1 N1 C5 C4 0.4(6) . . . . ? Zn1 N1 C5 C4 -170.0(3) . . . . ? C3 C4 C5 N1 3.1(6) . . . . ? C10 C6 C8 C7 -0.1(6) . . . . ? C9 C7 C8 C6 -0.6(6) . . . . ? C11 C7 C8 C6 172.9(4) . . . . ? C10 N3 C9 C7 0.6(6) . . . . ? Zn1 N3 C9 C7 -176.0(3) 4_476 . . . ? C8 C7 C9 N3 0.3(6) . . . . ? C11 C7 C9 N3 -173.4(3) . . . . ? C9 N3 C10 C6 -1.4(5) . . . . ? Zn1 N3 C10 C6 175.3(3) 4_476 . . . ? C8 C6 C10 N3 1.1(6) . . . . ? C3 N2 C11 O5 16.9(6) . . . . ? C3 N2 C11 C7 -160.5(4) . . . . ? C9 C7 C11 O5 44.1(5) . . . . ? C8 C7 C11 O5 -129.4(4) . . . . ? C9 C7 C11 N2 -138.4(4) . . . . ? C8 C7 C11 N2 48.1(5) . . . . ? Zn1 O1 C12 O2 -4.9(3) . . . . ? Zn1 O1 C12 C13 175.3(3) . . . . ? Zn1 O2 C12 O1 6.1(4) . . . . ? Zn1 O2 C12 C13 -174.2(3) . . . . ? O3 Zn1 C12 O1 -166.71(19) . . . . ? O2 Zn1 C12 O1 -174.6(4) . . . . ? N3 Zn1 C12 O1 68.2(2) 4_675 . . . ? N1 Zn1 C12 O1 -49.0(2) . . . . ? O3 Zn1 C12 O2 7.9(3) . . . . ? N3 Zn1 C12 O2 -117.2(2) 4_675 . . . ? N1 Zn1 C12 O2 125.6(2) . . . . ? O1 Zn1 C12 O2 174.6(4) . . . . ? O3 Zn1 C12 C13 34.7(14) . . . . ? O2 Zn1 C12 C13 26.8(13) . . . . ? N3 Zn1 C12 C13 -90.4(14) 4_675 . . . ? N1 Zn1 C12 C13 152.4(14) . . . . ? O1 Zn1 C12 C13 -158.6(15) . . . . ? O1 C12 C13 C13 -167.3(5) . . . 3_666 ? O2 C12 C13 C13 13.0(7) . . . 3_666 ? Zn1 C12 C13 C13 -10.6(18) . . . 3_666 ? Zn1 O3 C14 O4 12.2(5) . . . . ? Zn1 O3 C14 C15 -166.2(2) . . . . ? O4 C14 C15 C15 -164.9(5) . . . 3_465 ? O3 C14 C15 C15 13.6(7) . . . 3_465 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N O4 0.899(19) 1.95(2) 2.803(4) 156(4) 4_576 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.485 _refine_diff_density_min -0.438 _refine_diff_density_rms 0.108 data_twin51 _database_code_depnum_ccdc_archive 'CCDC 900362' #TrackingRef '0znsuc4pinadisordertwinfinal.cif' _audit_update_record ; 2012-08-30 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H13 N3 O5 Zn' _chemical_formula_weight 380.67 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 P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 9.664(2) _cell_length_b 9.582(2) _cell_length_c 16.414(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.430(3) _cell_angle_gamma 90.00 _cell_volume 1472.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.718 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 1.702 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5443 _exptl_absorpt_correction_T_max 0.7654 _exptl_absorpt_process_details TWINABS _exptl_special_details ; Reflections from both twin components used ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 23249 _diffrn_reflns_av_R_equivalents 0.0656 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.58 _reflns_number_total 3588 _reflns_number_gt 3408 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0000P)^2^+24.8802P] 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 3588 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1100 _refine_ls_R_factor_gt 0.1057 _refine_ls_wR_factor_ref 0.2234 _refine_ls_wR_factor_gt 0.2217 _refine_ls_goodness_of_fit_ref 1.309 _refine_ls_restrained_S_all 1.309 _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 0.34781(14) 0.38221(15) 0.44872(8) 0.0279(3) Uani 1 1 d . . . O4 O 0.3734(9) 0.3578(8) 0.5733(5) 0.0393(14) Uani 1 1 d . . . O3 O 0.5606(9) 0.4878(9) 0.6196(6) 0.045(2) Uani 1 1 d . . . O1 O 0.2012(7) 0.2400(8) 0.3999(5) 0.0294(19) Uani 1 1 d . . . O2 O 0.1881(10) 0.2982(9) 0.2662(5) 0.050(2) Uani 1 1 d . . . C12 C 0.4629(14) 0.4287(13) 0.6310(7) 0.037(3) Uani 1 1 d . . . C13 C 0.4359(15) 0.4117(19) 0.7155(8) 0.070(5) Uani 1 1 d . . . H13A H 0.3727 0.4883 0.7247 0.084 Uiso 1 1 calc R . . H13B H 0.3844 0.3228 0.7167 0.084 Uiso 1 1 calc R . . C14 C 0.1494(13) 0.2272(13) 0.3182(7) 0.033(3) Uani 1 1 d . . . C15 C 0.0443(13) 0.1069(14) 0.2958(6) 0.043(3) Uani 1 1 d . . . H15A H -0.0217 0.1102 0.3332 0.051 Uiso 1 1 calc R . . H15B H 0.0980 0.0180 0.3069 0.051 Uiso 1 1 calc R . . N1 N 0.174(3) 0.546(4) 0.440(2) 0.0393(14) Uani 0.547(9) 1 d P . 1 N3 N -0.484(3) 1.243(2) 0.4541(18) 0.0393(14) Uani 0.547(9) 1 d P . 1 N2 N -0.1991(15) 0.9180(15) 0.4508(10) 0.0237(12) Uani 0.547(9) 1 d P . 1 H2 H -0.1595 0.8875 0.5019 0.028 Uiso 0.547(9) 1 calc PR . 1 C6 C -0.154(2) 0.854(2) 0.3899(13) 0.0237(12) Uani 0.547(9) 1 d P . 1 O5 O -0.1898(16) 0.8964(17) 0.3234(10) 0.0237(12) Uani 0.547(9) 1 d P . 1 C1 C 0.148(4) 0.601(4) 0.5033(16) 0.0393(14) Uani 0.547(9) 1 d P . 1 H1 H 0.1978 0.5752 0.5587 0.047 Uiso 0.547(9) 1 calc PR . 1 C3 C -0.041(3) 0.742(3) 0.4139(17) 0.0393(14) Uani 0.547(9) 1 d P . 1 C5 C 0.096(3) 0.562(3) 0.3620(16) 0.0393(14) Uani 0.547(9) 1 d P . 1 H5 H 0.1093 0.5050 0.3170 0.047 Uiso 0.547(9) 1 calc PR . 1 C7 C -0.416(2) 1.184(2) 0.5231(13) 0.0237(12) Uani 0.547(9) 1 d P . 1 H7 H -0.4291 1.2168 0.5753 0.028 Uiso 0.547(9) 1 calc PR . 1 C2 C 0.031(3) 0.716(3) 0.4861(17) 0.0393(14) Uani 0.547(9) 1 d P . 1 H2A H 0.0140 0.7670 0.5321 0.047 Uiso 0.547(9) 1 calc PR . 1 C9 C -0.294(2) 1.021(2) 0.4474(16) 0.0237(12) Uani 0.547(9) 1 d P . 1 C10 C -0.363(2) 1.096(2) 0.3724(13) 0.0237(12) Uani 0.547(9) 1 d P . 1 H10 H -0.3465 1.0742 0.3191 0.028 Uiso 0.547(9) 1 calc PR . 1 C11 C -0.456(2) 1.204(2) 0.3830(14) 0.0237(12) Uani 0.547(9) 1 d P . 1 H11 H -0.5033 1.2541 0.3338 0.028 Uiso 0.547(9) 1 calc PR . 1 C4 C -0.016(3) 0.677(3) 0.3487(15) 0.0393(14) Uani 0.547(9) 1 d P . 1 H4 H -0.0672 0.7019 0.2934 0.047 Uiso 0.547(9) 1 calc PR . 1 C8 C -0.326(2) 1.071(2) 0.5222(14) 0.0237(12) Uani 0.547(9) 1 d P . 1 H8 H -0.2824 1.0266 0.5739 0.028 Uiso 0.547(9) 1 calc PR . 1 N1A N 0.198(4) 0.539(5) 0.451(3) 0.0393(14) Uani 0.453(9) 1 d P . 2 N3A N -0.490(4) 1.215(3) 0.441(2) 0.0393(14) Uani 0.453(9) 1 d P . 2 N2A N -0.1167(18) 0.8339(18) 0.4550(12) 0.0237(12) Uani 0.453(9) 1 d P . 2 H2A1 H -0.1309 0.8552 0.5045 0.028 Uiso 0.453(9) 1 calc PR . 2 C6A C -0.202(3) 0.898(3) 0.3897(15) 0.0237(12) Uani 0.453(9) 1 d P . 2 O5A O -0.222(2) 0.873(2) 0.3066(11) 0.0237(12) Uani 0.453(9) 1 d P . 2 C1A C 0.172(5) 0.589(4) 0.523(2) 0.0393(14) Uani 0.453(9) 1 d P . 2 H1A H 0.2309 0.5571 0.5746 0.047 Uiso 0.453(9) 1 calc PR . 2 C2A C 0.068(3) 0.683(3) 0.526(2) 0.0393(14) Uani 0.453(9) 1 d P . 2 H2A1 H 0.0513 0.7080 0.5788 0.047 Uiso 0.453(9) 1 calc PR . 2 C3A C -0.009(4) 0.739(3) 0.456(2) 0.0393(14) Uani 0.453(9) 1 d P . 2 C4A C 0.014(4) 0.681(3) 0.3802(19) 0.0393(14) Uani 0.453(9) 1 d P . 2 H4A H -0.0491 0.7014 0.3272 0.047 Uiso 0.453(9) 1 calc PR . 2 C5A C 0.131(3) 0.596(3) 0.386(2) 0.0393(14) Uani 0.453(9) 1 d P . 2 H5A H 0.1618 0.5794 0.3363 0.047 Uiso 0.453(9) 1 calc PR . 2 C7A C -0.406(3) 1.139(2) 0.5025(15) 0.0237(12) Uani 0.453(9) 1 d P . 2 H7A H -0.4196 1.1475 0.5577 0.028 Uiso 0.453(9) 1 calc PR . 2 C9A C -0.300(3) 1.000(3) 0.4106(18) 0.0237(12) Uani 0.453(9) 1 d P . 2 C10A C -0.399(3) 1.064(3) 0.3490(16) 0.0237(12) Uani 0.453(9) 1 d P . 2 H10A H -0.4067 1.0369 0.2924 0.028 Uiso 0.453(9) 1 calc PR . 2 C11A C -0.492(3) 1.169(3) 0.3640(16) 0.0237(12) Uani 0.453(9) 1 d P . 2 H11A H -0.5587 1.2091 0.3173 0.028 Uiso 0.453(9) 1 calc PR . 2 C8A C -0.302(3) 1.048(3) 0.4908(19) 0.0237(12) Uani 0.453(9) 1 d P . 2 H8A H -0.2308 1.0168 0.5382 0.028 Uiso 0.453(9) 1 calc PR . 2 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 0.0288(6) 0.0333(6) 0.0236(5) 0.0000(7) 0.0103(5) -0.0065(7) O4 0.053(4) 0.028(3) 0.038(4) -0.006(3) 0.015(3) 0.001(2) O3 0.056(6) 0.032(5) 0.059(6) 0.003(5) 0.038(5) -0.003(4) O1 0.020(4) 0.035(5) 0.028(4) -0.012(4) -0.004(3) 0.002(3) O2 0.067(7) 0.048(6) 0.035(5) 0.015(4) 0.015(5) -0.001(5) C12 0.047(8) 0.048(8) 0.022(6) -0.008(5) 0.017(6) -0.015(6) C13 0.070(11) 0.110(15) 0.032(7) -0.010(8) 0.015(7) -0.039(10) C14 0.038(7) 0.031(7) 0.029(6) -0.001(6) 0.010(5) 0.004(5) C15 0.046(7) 0.043(7) 0.023(6) -0.006(6) -0.020(5) -0.005(7) N1 0.053(4) 0.028(3) 0.038(4) -0.006(3) 0.015(3) 0.001(2) N3 0.053(4) 0.028(3) 0.038(4) -0.006(3) 0.015(3) 0.001(2) N2 0.020(3) 0.017(3) 0.027(3) -0.007(3) -0.007(3) 0.0011(19) C6 0.020(3) 0.017(3) 0.027(3) -0.007(3) -0.007(3) 0.0011(19) O5 0.020(3) 0.017(3) 0.027(3) -0.007(3) -0.007(3) 0.0011(19) C1 0.053(4) 0.028(3) 0.038(4) -0.006(3) 0.015(3) 0.001(2) C3 0.053(4) 0.028(3) 0.038(4) -0.006(3) 0.015(3) 0.001(2) C5 0.053(4) 0.028(3) 0.038(4) -0.006(3) 0.015(3) 0.001(2) C7 0.020(3) 0.017(3) 0.027(3) -0.007(3) -0.007(3) 0.0011(19) C2 0.053(4) 0.028(3) 0.038(4) -0.006(3) 0.015(3) 0.001(2) C9 0.020(3) 0.017(3) 0.027(3) -0.007(3) -0.007(3) 0.0011(19) C10 0.020(3) 0.017(3) 0.027(3) -0.007(3) -0.007(3) 0.0011(19) C11 0.020(3) 0.017(3) 0.027(3) -0.007(3) -0.007(3) 0.0011(19) C4 0.053(4) 0.028(3) 0.038(4) -0.006(3) 0.015(3) 0.001(2) C8 0.020(3) 0.017(3) 0.027(3) -0.007(3) -0.007(3) 0.0011(19) N1A 0.053(4) 0.028(3) 0.038(4) -0.006(3) 0.015(3) 0.001(2) N3A 0.053(4) 0.028(3) 0.038(4) -0.006(3) 0.015(3) 0.001(2) N2A 0.020(3) 0.017(3) 0.027(3) -0.007(3) -0.007(3) 0.0011(19) C6A 0.020(3) 0.017(3) 0.027(3) -0.007(3) -0.007(3) 0.0011(19) O5A 0.020(3) 0.017(3) 0.027(3) -0.007(3) -0.007(3) 0.0011(19) C1A 0.053(4) 0.028(3) 0.038(4) -0.006(3) 0.015(3) 0.001(2) C2A 0.053(4) 0.028(3) 0.038(4) -0.006(3) 0.015(3) 0.001(2) C3A 0.053(4) 0.028(3) 0.038(4) -0.006(3) 0.015(3) 0.001(2) C4A 0.053(4) 0.028(3) 0.038(4) -0.006(3) 0.015(3) 0.001(2) C5A 0.053(4) 0.028(3) 0.038(4) -0.006(3) 0.015(3) 0.001(2) C7A 0.020(3) 0.017(3) 0.027(3) -0.007(3) -0.007(3) 0.0011(19) C9A 0.020(3) 0.017(3) 0.027(3) -0.007(3) -0.007(3) 0.0011(19) C10A 0.020(3) 0.017(3) 0.027(3) -0.007(3) -0.007(3) 0.0011(19) C11A 0.020(3) 0.017(3) 0.027(3) -0.007(3) -0.007(3) 0.0011(19) C8A 0.020(3) 0.017(3) 0.027(3) -0.007(3) -0.007(3) 0.0011(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 O1 1.985(7) . ? Zn1 O4 2.012(8) . ? Zn1 O3 2.021(8) 3_666 ? Zn1 N3 2.09(3) 1_645 ? Zn1 N1A 2.09(4) . ? Zn1 N3A 2.26(3) 1_645 ? Zn1 N1 2.27(3) . ? O4 C12 1.302(13) . ? O3 C12 1.156(13) . ? O3 Zn1 2.021(8) 3_666 ? O1 C14 1.315(13) . ? O2 C14 1.221(13) . ? C12 C13 1.483(16) . ? C13 C13 1.45(3) 2_656 ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.520(17) . ? C15 C15 1.532(17) 2 ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? N1 C1 1.25(5) . ? N1 C5 1.32(4) . ? N3 C7 1.29(4) . ? N3 C11 1.32(4) . ? N3 Zn1 2.09(3) 1_465 ? N2 C6 1.33(3) . ? N2 C9 1.34(2) . ? N2 H2 0.8800 . ? C6 O5 1.13(2) . ? C6 C3 1.51(3) . ? C1 C2 1.55(4) . ? C1 H1 0.9500 . ? C3 C2 1.24(3) . ? C3 C4 1.31(3) . ? C5 C4 1.52(4) . ? C5 H5 0.9500 . ? C7 C8 1.39(3) . ? C7 H7 0.9500 . ? C2 H2A 0.9500 . ? C9 C8 1.42(3) . ? C9 C10 1.44(3) . ? C10 C11 1.41(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C4 H4 0.9500 . ? C8 H8 0.9500 . ? N1A C5A 1.23(5) . ? N1A C1A 1.35(6) . ? N3A C11A 1.34(4) . ? N3A C7A 1.34(4) . ? N3A Zn1 2.26(3) 1_465 ? N2A C6A 1.33(3) . ? N2A C3A 1.38(4) . ? N2A H2A1 0.8800 . ? C6A O5A 1.35(3) . ? C6A C9A 1.46(4) . ? C1A C2A 1.36(5) . ? C1A H1A 0.9500 . ? C2A C3A 1.32(4) . ? C2A H2A1 0.9500 . ? C3A C4A 1.44(4) . ? C4A C5A 1.38(4) . ? C4A H4A 0.9500 . ? C5A H5A 0.9500 . ? C7A C8A 1.38(3) . ? C7A H7A 0.9500 . ? C9A C10A 1.35(3) . ? C9A C8A 1.40(3) . ? C10A C11A 1.41(3) . ? C10A H10A 0.9500 . ? C11A H11A 0.9500 . ? C8A H8A 0.9500 . ? 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 O4 103.0(3) . . ? O1 Zn1 O3 124.5(3) . 3_666 ? O4 Zn1 O3 132.5(4) . 3_666 ? O1 Zn1 N3 92.8(7) . 1_645 ? O4 Zn1 N3 89.2(8) . 1_645 ? O3 Zn1 N3 88.4(9) 3_666 1_645 ? O1 Zn1 N1A 94.1(13) . . ? O4 Zn1 N1A 88.4(12) . . ? O3 Zn1 N1A 88.4(14) 3_666 . ? N3 Zn1 N1A 173.0(15) 1_645 . ? O1 Zn1 N3A 85.8(9) . 1_645 ? O4 Zn1 N3A 93.6(9) . 1_645 ? O3 Zn1 N3A 90.0(10) 3_666 1_645 ? N1A Zn1 N3A 178.0(16) . 1_645 ? O1 Zn1 N1 90.4(10) . . ? O4 Zn1 N1 92.7(10) . . ? O3 Zn1 N1 87.5(11) 3_666 . ? N3 Zn1 N1 175.8(14) 1_645 . ? N3A Zn1 N1 173.2(13) 1_645 . ? C12 O4 Zn1 124.7(7) . . ? C12 O3 Zn1 151.7(10) . 3_666 ? C14 O1 Zn1 121.9(8) . . ? O3 C12 O4 124.0(11) . . ? O3 C12 C13 123.1(12) . . ? O4 C12 C13 112.5(11) . . ? C13 C13 C12 114.5(16) 2_656 . ? C13 C13 H13A 108.6 2_656 . ? C12 C13 H13A 108.6 . . ? C13 C13 H13B 108.6 2_656 . ? C12 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? O2 C14 O1 123.8(12) . . ? O2 C14 C15 123.8(11) . . ? O1 C14 C15 112.3(10) . . ? C14 C15 C15 114.4(9) . 2 ? C14 C15 H15A 108.6 . . ? C15 C15 H15A 108.6 2 . ? C14 C15 H15B 108.6 . . ? C15 C15 H15B 108.6 2 . ? H15A C15 H15B 107.6 . . ? C1 N1 C5 125(3) . . ? C1 N1 Zn1 122(2) . . ? C5 N1 Zn1 112(3) . . ? C7 N3 C11 119(2) . . ? C7 N3 Zn1 122.5(19) . 1_465 ? C11 N3 Zn1 118(2) . 1_465 ? C6 N2 C9 131(2) . . ? C6 N2 H2 114.5 . . ? C9 N2 H2 114.5 . . ? O5 C6 N2 119(2) . . ? O5 C6 C3 122(2) . . ? N2 C6 C3 118.7(19) . . ? N1 C1 C2 116(2) . . ? N1 C1 H1 122.0 . . ? C2 C1 H1 122.0 . . ? C2 C3 C4 121(3) . . ? C2 C3 C6 126(2) . . ? C4 C3 C6 113(2) . . ? N1 C5 C4 116(3) . . ? N1 C5 H5 122.1 . . ? C4 C5 H5 122.1 . . ? N3 C7 C8 121(2) . . ? N3 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C3 C2 C1 122(2) . . ? C3 C2 H2A 119.1 . . ? C1 C2 H2A 119.1 . . ? N2 C9 C8 120(2) . . ? N2 C9 C10 125(2) . . ? C8 C9 C10 114.6(18) . . ? C11 C10 C9 116(2) . . ? C11 C10 H10 122.1 . . ? C9 C10 H10 122.1 . . ? N3 C11 C10 126(2) . . ? N3 C11 H11 116.8 . . ? C10 C11 H11 116.8 . . ? C3 C4 C5 120(2) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C7 C8 C9 123(2) . . ? C7 C8 H8 118.5 . . ? C9 C8 H8 118.5 . . ? C5A N1A C1A 115(4) . . ? C5A N1A Zn1 121(3) . . ? C1A N1A Zn1 124(3) . . ? C11A N3A C7A 113(3) . . ? C11A N3A Zn1 116(3) . 1_465 ? C7A N3A Zn1 130(2) . 1_465 ? C6A N2A C3A 129(3) . . ? C6A N2A H2A1 115.4 . . ? C3A N2A H2A1 115.4 . . ? N2A C6A O5A 129(2) . . ? N2A C6A C9A 115(2) . . ? O5A C6A C9A 115(2) . . ? N1A C1A C2A 125(3) . . ? N1A C1A H1A 117.5 . . ? C2A C1A H1A 117.5 . . ? C3A C2A C1A 120(3) . . ? C3A C2A H2A1 120.0 . . ? C1A C2A H2A1 120.0 . . ? C2A C3A N2A 123(3) . . ? C2A C3A C4A 115(3) . . ? N2A C3A C4A 122(3) . . ? C5A C4A C3A 118(3) . . ? C5A C4A H4A 120.9 . . ? C3A C4A H4A 120.9 . . ? N1A C5A C4A 125(3) . . ? N1A C5A H5A 117.7 . . ? C4A C5A H5A 117.7 . . ? N3A C7A C8A 124(3) . . ? N3A C7A H7A 117.8 . . ? C8A C7A H7A 117.8 . . ? C10A C9A C8A 112(2) . . ? C10A C9A C6A 121(2) . . ? C8A C9A C6A 127(2) . . ? C9A C10A C11A 124(2) . . ? C9A C10A H10A 118.1 . . ? C11A C10A H10A 118.1 . . ? N3A C11A C10A 123(3) . . ? N3A C11A H11A 118.6 . . ? C10A C11A H11A 118.6 . . ? C7A C8A C9A 121(2) . . ? C7A C8A H8A 119.4 . . ? C9A C8A H8A 119.4 . . ? 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 O1 Zn1 O4 C12 178.6(9) . . . . ? O3 Zn1 O4 C12 -1.3(11) 3_666 . . . ? N3 Zn1 O4 C12 85.9(12) 1_645 . . . ? N1A Zn1 O4 C12 -87.6(16) . . . . ? N3A Zn1 O4 C12 92.1(13) 1_645 . . . ? N1 Zn1 O4 C12 -90.4(14) . . . . ? O4 Zn1 O1 C14 176.6(8) . . . . ? O3 Zn1 O1 C14 -3.5(10) 3_666 . . . ? N3 Zn1 O1 C14 -93.5(11) 1_645 . . . ? N1A Zn1 O1 C14 87.3(15) . . . . ? N3A Zn1 O1 C14 -90.6(12) 1_645 . . . ? N1 Zn1 O1 C14 83.7(13) . . . . ? Zn1 O3 C12 O4 47(3) 3_666 . . . ? Zn1 O3 C12 C13 -140.9(16) 3_666 . . . ? Zn1 O4 C12 O3 -19.8(19) . . . . ? Zn1 O4 C12 C13 167.1(10) . . . . ? O3 C12 C13 C13 -28.2(17) . . . 2_656 ? O4 C12 C13 C13 145.0(8) . . . 2_656 ? Zn1 O1 C14 O2 1.5(16) . . . . ? Zn1 O1 C14 C15 177.2(8) . . . . ? O2 C14 C15 C15 -17(2) . . . 2 ? O1 C14 C15 C15 166.9(12) . . . 2 ? O1 Zn1 N1 C1 115(3) . . . . ? O4 Zn1 N1 C1 12(4) . . . . ? O3 Zn1 N1 C1 -121(3) 3_666 . . . ? N3 Zn1 N1 C1 -106(15) 1_645 . . . ? N1A Zn1 N1 C1 -21(25) . . . . ? N3A Zn1 N1 C1 171(11) 1_645 . . . ? O1 Zn1 N1 C5 -58(3) . . . . ? O4 Zn1 N1 C5 -161(3) . . . . ? O3 Zn1 N1 C5 67(3) 3_666 . . . ? N3 Zn1 N1 C5 81(15) 1_645 . . . ? N1A Zn1 N1 C5 166(30) . . . . ? N3A Zn1 N1 C5 -2(14) 1_645 . . . ? C9 N2 C6 O5 7(3) . . . . ? C9 N2 C6 C3 178.7(19) . . . . ? C5 N1 C1 C2 -11(6) . . . . ? Zn1 N1 C1 C2 178(2) . . . . ? O5 C6 C3 C2 159(3) . . . . ? N2 C6 C3 C2 -12(4) . . . . ? O5 C6 C3 C4 -15(3) . . . . ? N2 C6 C3 C4 174(2) . . . . ? C1 N1 C5 C4 12(6) . . . . ? Zn1 N1 C5 C4 -175.7(19) . . . . ? C11 N3 C7 C8 -6(4) . . . . ? Zn1 N3 C7 C8 166.9(16) 1_465 . . . ? C4 C3 C2 C1 -3(4) . . . . ? C6 C3 C2 C1 -178(3) . . . . ? N1 C1 C2 C3 6(5) . . . . ? C6 N2 C9 C8 179.4(18) . . . . ? C6 N2 C9 C10 -6(3) . . . . ? N2 C9 C10 C11 -177.8(19) . . . . ? C8 C9 C10 C11 -3(3) . . . . ? C7 N3 C11 C10 4(4) . . . . ? Zn1 N3 C11 C10 -169.4(17) 1_465 . . . ? C9 C10 C11 N3 1(3) . . . . ? C2 C3 C4 C5 4(4) . . . . ? C6 C3 C4 C5 179(2) . . . . ? N1 C5 C4 C3 -8(4) . . . . ? N3 C7 C8 C9 4(3) . . . . ? N2 C9 C8 C7 175.9(18) . . . . ? C10 C9 C8 C7 1(3) . . . . ? O1 Zn1 N1A C5A -73(4) . . . . ? O4 Zn1 N1A C5A -176(4) . . . . ? O3 Zn1 N1A C5A 52(4) 3_666 . . . ? N3 Zn1 N1A C5A 114(12) 1_645 . . . ? N3A Zn1 N1A C5A 15(44) 1_645 . . . ? N1 Zn1 N1A C5A -29(24) . . . . ? O1 Zn1 N1A C1A 110(4) . . . . ? O4 Zn1 N1A C1A 8(4) . . . . ? O3 Zn1 N1A C1A -125(4) 3_666 . . . ? N3 Zn1 N1A C1A -62(15) 1_645 . . . ? N3A Zn1 N1A C1A -162(39) 1_645 . . . ? N1 Zn1 N1A C1A 154(30) . . . . ? C3A N2A C6A O5A 11(4) . . . . ? C3A N2A C6A C9A -176(3) . . . . ? C5A N1A C1A C2A 8(6) . . . . ? Zn1 N1A C1A C2A -175(3) . . . . ? N1A C1A C2A C3A -5(6) . . . . ? C1A C2A C3A N2A 179(3) . . . . ? C1A C2A C3A C4A 7(4) . . . . ? C6A N2A C3A C2A -180(3) . . . . ? C6A N2A C3A C4A -8(5) . . . . ? C2A C3A C4A C5A -13(4) . . . . ? N2A C3A C4A C5A 175(3) . . . . ? C1A N1A C5A C4A -15(6) . . . . ? Zn1 N1A C5A C4A 168(3) . . . . ? C3A C4A C5A N1A 18(6) . . . . ? C11A N3A C7A C8A 17(5) . . . . ? Zn1 N3A C7A C8A -174(2) 1_465 . . . ? N2A C6A C9A C10A -175(2) . . . . ? O5A C6A C9A C10A -1(4) . . . . ? N2A C6A C9A C8A 7(4) . . . . ? O5A C6A C9A C8A -179(2) . . . . ? C8A C9A C10A C11A 1(4) . . . . ? C6A C9A C10A C11A -176(2) . . . . ? C7A N3A C11A C10A -9(5) . . . . ? Zn1 N3A C11A C10A -179.0(19) 1_465 . . . ? C9A C10A C11A N3A 0(4) . . . . ? N3A C7A C8A C9A -17(4) . . . . ? C10A C9A C8A C7A 7(4) . . . . ? C6A C9A C8A C7A -176(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 N2 H2 O1 0.88 2.14 2.885(18) 142.1 3_566 N2A H2A1 O1 0.88 2.07 2.79(2) 138.9 3_566 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.868 _refine_diff_density_min -1.780 _refine_diff_density_rms 0.174 data_p21c2 _database_code_depnum_ccdc_archive 'CCDC 900363' #TrackingRef 'znmaleateOH4pinafinal.cif' _audit_update_record ; 2012-08-30 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; Zn3(maleate)2(OH)2(4-pina)2 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H24 N6 O12 Zn3' _chemical_formula_weight 856.66 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 P2(1)/c 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 11.4026(15) _cell_length_b 7.6683(10) _cell_length_c 17.686(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.380(2) _cell_angle_gamma 90.00 _cell_volume 1536.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6986 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 25.32 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.851 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 2.401 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4506 _exptl_absorpt_correction_T_max 0.7815 _exptl_absorpt_process_details SADABS _exptl_special_details ? _diffrn_ambient_temperature 173(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11950 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.30 _reflns_number_total 2783 _reflns_number_gt 2445 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+1.0516P] 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 2783 _refine_ls_number_parameters 238 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0292 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_ref 0.0632 _refine_ls_wR_factor_gt 0.0606 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.88045(2) 0.14034(3) 0.567941(15) 0.01567(9) Uani 1 1 d . . . Zn2 Zn 1.0000 0.5000 0.5000 0.01500(11) Uani 1 2 d S . . O5 O 1.00378(13) 0.2382(2) 0.51570(9) 0.0162(3) Uani 1 1 d D . . H5A H 1.012(2) 0.198(3) 0.4731(10) 0.019 Uiso 1 1 d D . . O3 O 0.85572(15) -0.7062(2) 0.65380(9) 0.0223(4) Uani 1 1 d . . . O2 O 0.74511(15) -0.1106(2) 0.63324(10) 0.0270(4) Uani 1 1 d . . . O1 O 0.93617(14) -0.0743(2) 0.62599(9) 0.0180(4) Uani 1 1 d . . . N2 N 0.16026(17) -0.0097(2) 0.08360(11) 0.0186(4) Uani 1 1 d . . . N1 N 0.74221(17) 0.1079(3) 0.48626(11) 0.0194(4) Uani 1 1 d . . . O4 O 0.88486(14) -0.4656(2) 0.58677(9) 0.0193(4) Uani 1 1 d . . . C14 C 0.8494(2) -0.1467(3) 0.65395(13) 0.0172(5) Uani 1 1 d . . . C13 C 0.8767(2) -0.2677(3) 0.72032(13) 0.0183(5) Uani 1 1 d . . . H13 H 0.8914 -0.2143 0.7689 0.022 Uiso 1 1 calc R . . C12 C 0.6751(2) 0.0080(3) 0.36097(14) 0.0239(6) Uani 1 1 d . . . H12 H 0.6927 -0.0492 0.3159 0.029 Uiso 1 1 calc R . . C11 C 0.8826(2) -0.4397(3) 0.71904(13) 0.0183(5) Uani 1 1 d . . . H11 H 0.8939 -0.5002 0.7661 0.022 Uiso 1 1 calc R . . C10 C 0.2701(2) -0.0820(3) 0.20291(14) 0.0229(5) Uani 1 1 d . . . H10 H 0.2726 -0.1387 0.2508 0.027 Uiso 1 1 calc R . . C9 C 0.7606(2) 0.0289(3) 0.42139(14) 0.0236(6) Uani 1 1 d . . . H9 H 0.8372 -0.0155 0.4167 0.028 Uiso 1 1 calc R . . C8 C 0.8725(2) -0.5434(3) 0.64747(13) 0.0166(5) Uani 1 1 d . . . C7 C 0.3574(2) 0.0930(3) 0.11326(15) 0.0265(6) Uani 1 1 d . . . H7 H 0.4225 0.1558 0.0978 0.032 Uiso 1 1 calc R . . C6 C 0.6328(2) 0.1685(3) 0.49167(15) 0.0277(6) Uani 1 1 d . . . H6 H 0.6175 0.2248 0.5374 0.033 Uiso 1 1 calc R . . C5 C 0.2540(2) 0.0811(3) 0.06596(14) 0.0251(6) Uani 1 1 d . . . H5 H 0.2484 0.1399 0.0184 0.030 Uiso 1 1 calc R . . C4 C 0.3661(2) 0.0126(3) 0.18377(14) 0.0231(6) Uani 1 1 d . . . C2 C 0.5424(2) 0.1528(4) 0.43424(15) 0.0293(6) Uani 1 1 d . . . H2 H 0.4663 0.1970 0.4406 0.035 Uiso 1 1 calc R . . C1 C 0.5626(2) 0.0721(3) 0.36689(14) 0.0215(5) Uani 1 1 d . . . O6 O 0.57393(17) 0.0229(4) 0.20714(11) 0.0546(7) Uani 1 1 d . . . C15 C 0.1705(2) -0.0921(3) 0.15057(14) 0.0206(5) Uani 1 1 d . . . H15 H 0.1061 -0.1611 0.1630 0.025 Uiso 1 1 calc R . . C16 C 0.4805(2) 0.0286(4) 0.23405(15) 0.0284(6) Uani 1 1 d . . . N3 N 0.46953(18) 0.0547(3) 0.30917(12) 0.0249(5) Uani 1 1 d D . . H3N H 0.3989(17) 0.080(4) 0.3194(15) 0.030 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 0.01520(15) 0.01456(15) 0.01670(15) 0.00054(10) -0.00072(11) -0.00091(11) Zn2 0.0162(2) 0.0137(2) 0.0145(2) 0.00114(15) -0.00068(15) -0.00069(15) O5 0.0168(8) 0.0139(8) 0.0181(8) -0.0004(7) 0.0026(7) -0.0008(7) O3 0.0331(10) 0.0133(8) 0.0216(9) -0.0006(7) 0.0072(7) -0.0012(7) O2 0.0195(9) 0.0351(11) 0.0263(9) 0.0056(8) 0.0023(8) 0.0043(8) O1 0.0188(9) 0.0155(8) 0.0199(8) 0.0013(7) 0.0026(7) 0.0002(7) N2 0.0184(10) 0.0175(10) 0.0188(10) -0.0026(8) -0.0032(8) 0.0021(8) N1 0.0163(10) 0.0196(11) 0.0213(11) 0.0031(8) -0.0023(8) -0.0031(8) O4 0.0239(9) 0.0190(9) 0.0154(8) 0.0010(7) 0.0035(7) 0.0021(7) C14 0.0227(13) 0.0137(11) 0.0153(11) -0.0058(9) 0.0024(10) 0.0018(10) C13 0.0189(12) 0.0212(13) 0.0148(11) -0.0015(10) 0.0019(9) -0.0009(10) C12 0.0218(13) 0.0264(14) 0.0226(13) -0.0019(11) -0.0022(11) -0.0003(11) C11 0.0207(12) 0.0190(12) 0.0153(11) 0.0024(10) 0.0019(10) 0.0007(10) C10 0.0266(14) 0.0219(13) 0.0191(12) -0.0009(10) -0.0018(11) 0.0058(11) C9 0.0167(12) 0.0276(14) 0.0253(13) 0.0011(11) -0.0025(11) 0.0019(11) C8 0.0141(11) 0.0177(12) 0.0180(12) 0.0009(10) 0.0009(9) 0.0018(9) C7 0.0213(13) 0.0275(14) 0.0299(14) -0.0018(11) -0.0012(11) -0.0045(11) C6 0.0215(14) 0.0367(16) 0.0248(13) -0.0056(12) 0.0015(11) -0.0003(12) C5 0.0263(14) 0.0246(14) 0.0235(13) 0.0010(11) -0.0017(11) -0.0026(11) C4 0.0205(13) 0.0241(13) 0.0239(13) -0.0048(11) -0.0021(11) 0.0053(11) C2 0.0163(13) 0.0422(17) 0.0286(14) -0.0035(12) -0.0010(11) 0.0044(11) C1 0.0175(12) 0.0219(13) 0.0237(13) 0.0032(11) -0.0034(10) -0.0030(10) O6 0.0197(11) 0.115(2) 0.0280(11) -0.0084(12) -0.0022(9) 0.0057(12) C15 0.0199(12) 0.0181(12) 0.0232(13) -0.0047(10) -0.0006(10) 0.0024(10) C16 0.0219(14) 0.0358(15) 0.0271(14) -0.0032(12) 0.0010(12) 0.0026(12) N3 0.0170(11) 0.0350(13) 0.0219(11) -0.0019(10) -0.0015(9) 0.0017(10) _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 O5 1.9191(16) . ? Zn1 O3 1.9660(16) 1_565 ? Zn1 O1 2.0052(16) . ? Zn1 N1 2.032(2) . ? Zn2 O5 2.0264(16) 3_766 ? Zn2 O5 2.0264(16) . ? Zn2 O4 2.1439(16) 3_756 ? Zn2 O4 2.1439(16) 1_565 ? Zn2 N2 2.2205(19) 2_655 ? Zn2 N2 2.2205(19) 4_666 ? O5 H5A 0.830(16) . ? O3 C8 1.270(3) . ? O3 Zn1 1.9661(16) 1_545 ? O2 C14 1.237(3) . ? O1 C14 1.281(3) . ? N2 C15 1.336(3) . ? N2 C5 1.341(3) . ? N2 Zn2 2.2205(19) 2_645 ? N1 C9 1.334(3) . ? N1 C6 1.345(3) . ? O4 C8 1.250(3) . ? O4 Zn2 2.1439(16) 1_545 ? C14 C13 1.501(3) . ? C13 C11 1.321(3) . ? C13 H13 0.9500 . ? C12 C9 1.373(3) . ? C12 C1 1.389(3) . ? C12 H12 0.9500 . ? C11 C8 1.488(3) . ? C11 H11 0.9500 . ? C10 C15 1.386(3) . ? C10 C4 1.386(4) . ? C10 H10 0.9500 . ? C9 H9 0.9500 . ? C7 C5 1.371(4) . ? C7 C4 1.385(4) . ? C7 H7 0.9500 . ? C6 C2 1.369(4) . ? C6 H6 0.9500 . ? C5 H5 0.9500 . ? C4 C16 1.500(3) . ? C2 C1 1.384(4) . ? C2 H2 0.9500 . ? C1 N3 1.395(3) . ? O6 C16 1.215(3) . ? C15 H15 0.9500 . ? C16 N3 1.363(3) . ? N3 H3N 0.867(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 O5 Zn1 O3 108.27(7) . 1_565 ? O5 Zn1 O1 111.10(7) . . ? O3 Zn1 O1 99.22(7) 1_565 . ? O5 Zn1 N1 104.93(7) . . ? O3 Zn1 N1 117.12(8) 1_565 . ? O1 Zn1 N1 116.12(7) . . ? O5 Zn2 O5 180.0 3_766 . ? O5 Zn2 O4 91.68(6) 3_766 3_756 ? O5 Zn2 O4 88.32(6) . 3_756 ? O5 Zn2 O4 88.32(6) 3_766 1_565 ? O5 Zn2 O4 91.68(6) . 1_565 ? O4 Zn2 O4 180.0 3_756 1_565 ? O5 Zn2 N2 86.48(7) 3_766 2_655 ? O5 Zn2 N2 93.52(7) . 2_655 ? O4 Zn2 N2 92.48(7) 3_756 2_655 ? O4 Zn2 N2 87.52(7) 1_565 2_655 ? O5 Zn2 N2 93.52(7) 3_766 4_666 ? O5 Zn2 N2 86.48(7) . 4_666 ? O4 Zn2 N2 87.52(7) 3_756 4_666 ? O4 Zn2 N2 92.48(7) 1_565 4_666 ? N2 Zn2 N2 180.0 2_655 4_666 ? Zn1 O5 Zn2 116.61(8) . . ? Zn1 O5 H5A 117.0(18) . . ? Zn2 O5 H5A 104.4(18) . . ? C8 O3 Zn1 118.98(14) . 1_545 ? C14 O1 Zn1 109.84(14) . . ? C15 N2 C5 117.3(2) . . ? C15 N2 Zn2 126.19(16) . 2_645 ? C5 N2 Zn2 116.47(16) . 2_645 ? C9 N1 C6 117.0(2) . . ? C9 N1 Zn1 118.91(16) . . ? C6 N1 Zn1 124.04(17) . . ? C8 O4 Zn2 133.84(15) . 1_545 ? O2 C14 O1 123.2(2) . . ? O2 C14 C13 118.6(2) . . ? O1 C14 C13 117.9(2) . . ? C11 C13 C14 127.6(2) . . ? C11 C13 H13 116.2 . . ? C14 C13 H13 116.2 . . ? C9 C12 C1 118.8(2) . . ? C9 C12 H12 120.6 . . ? C1 C12 H12 120.6 . . ? C13 C11 C8 123.3(2) . . ? C13 C11 H11 118.4 . . ? C8 C11 H11 118.4 . . ? C15 C10 C4 118.5(2) . . ? C15 C10 H10 120.7 . . ? C4 C10 H10 120.7 . . ? N1 C9 C12 123.8(2) . . ? N1 C9 H9 118.1 . . ? C12 C9 H9 118.1 . . ? O4 C8 O3 125.3(2) . . ? O4 C8 C11 118.0(2) . . ? O3 C8 C11 116.7(2) . . ? C5 C7 C4 119.4(2) . . ? C5 C7 H7 120.3 . . ? C4 C7 H7 120.3 . . ? N1 C6 C2 123.0(2) . . ? N1 C6 H6 118.5 . . ? C2 C6 H6 118.5 . . ? N2 C5 C7 123.1(2) . . ? N2 C5 H5 118.4 . . ? C7 C5 H5 118.4 . . ? C7 C4 C10 118.2(2) . . ? C7 C4 C16 117.9(2) . . ? C10 C4 C16 123.8(2) . . ? C6 C2 C1 119.7(2) . . ? C6 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C1 C12 117.8(2) . . ? C2 C1 N3 119.2(2) . . ? C12 C1 N3 123.0(2) . . ? N2 C15 C10 123.4(2) . . ? N2 C15 H15 118.3 . . ? C10 C15 H15 118.3 . . ? O6 C16 N3 124.5(2) . . ? O6 C16 C4 120.5(2) . . ? N3 C16 C4 114.9(2) . . ? C16 N3 C1 125.6(2) . . ? C16 N3 H3N 115.1(19) . . ? C1 N3 H3N 118.4(19) . . ? 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 O3 Zn1 O5 Zn2 -42.08(10) 1_565 . . . ? O1 Zn1 O5 Zn2 -150.03(8) . . . . ? N1 Zn1 O5 Zn2 83.71(10) . . . . ? O5 Zn2 O5 Zn1 37(43) 3_766 . . . ? O4 Zn2 O5 Zn1 -161.86(9) 3_756 . . . ? O4 Zn2 O5 Zn1 18.14(9) 1_565 . . . ? N2 Zn2 O5 Zn1 -69.48(9) 2_655 . . . ? N2 Zn2 O5 Zn1 110.52(9) 4_666 . . . ? O5 Zn1 O1 C14 -173.53(14) . . . . ? O3 Zn1 O1 C14 72.70(15) 1_565 . . . ? N1 Zn1 O1 C14 -53.74(16) . . . . ? O5 Zn1 N1 C9 49.06(19) . . . . ? O3 Zn1 N1 C9 169.13(17) 1_565 . . . ? O1 Zn1 N1 C9 -74.02(19) . . . . ? O5 Zn1 N1 C6 -127.7(2) . . . . ? O3 Zn1 N1 C6 -7.7(2) 1_565 . . . ? O1 Zn1 N1 C6 109.2(2) . . . . ? Zn1 O1 C14 O2 14.9(3) . . . . ? Zn1 O1 C14 C13 -158.78(16) . . . . ? O2 C14 C13 C11 88.0(3) . . . . ? O1 C14 C13 C11 -98.0(3) . . . . ? C14 C13 C11 C8 5.5(4) . . . . ? C6 N1 C9 C12 0.5(4) . . . . ? Zn1 N1 C9 C12 -176.6(2) . . . . ? C1 C12 C9 N1 0.0(4) . . . . ? Zn2 O4 C8 O3 -53.8(3) 1_545 . . . ? Zn2 O4 C8 C11 123.7(2) 1_545 . . . ? Zn1 O3 C8 O4 12.5(3) 1_545 . . . ? Zn1 O3 C8 C11 -164.96(15) 1_545 . . . ? C13 C11 C8 O4 16.1(3) . . . . ? C13 C11 C8 O3 -166.2(2) . . . . ? C9 N1 C6 C2 -0.3(4) . . . . ? Zn1 N1 C6 C2 176.6(2) . . . . ? C15 N2 C5 C7 -0.3(4) . . . . ? Zn2 N2 C5 C7 177.4(2) 2_645 . . . ? C4 C7 C5 N2 -2.0(4) . . . . ? C5 C7 C4 C10 1.9(4) . . . . ? C5 C7 C4 C16 -179.9(2) . . . . ? C15 C10 C4 C7 0.2(4) . . . . ? C15 C10 C4 C16 -177.8(2) . . . . ? N1 C6 C2 C1 -0.3(4) . . . . ? C6 C2 C1 C12 0.7(4) . . . . ? C6 C2 C1 N3 179.1(2) . . . . ? C9 C12 C1 C2 -0.6(4) . . . . ? C9 C12 C1 N3 -178.9(2) . . . . ? C5 N2 C15 C10 2.7(4) . . . . ? Zn2 N2 C15 C10 -174.78(17) 2_645 . . . ? C4 C10 C15 N2 -2.6(4) . . . . ? C7 C4 C16 O6 -38.5(4) . . . . ? C10 C4 C16 O6 139.6(3) . . . . ? C7 C4 C16 N3 139.6(3) . . . . ? C10 C4 C16 N3 -42.3(4) . . . . ? O6 C16 N3 C1 -2.5(5) . . . . ? C4 C16 N3 C1 179.5(2) . . . . ? C2 C1 N3 C16 159.0(3) . . . . ? C12 C1 N3 C16 -22.7(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 O5 H5A O1 0.830(16) 2.133(17) 2.951(2) 169(3) 3_756 N3 H3N O2 0.867(17) 1.939(18) 2.787(3) 166(3) 3_656 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.642 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.065 data_p21n _database_code_depnum_ccdc_archive 'CCDC 900879' #TrackingRef '0znsucc4pnafinal.cif' _audit_update_record ; 2012-09-11 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H13 N3 O5 Zn' _chemical_formula_weight 380.65 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 P2(1)/n 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 7.3106(7) _cell_length_b 18.8655(17) _cell_length_c 10.8996(10) _cell_angle_alpha 90.00 _cell_angle_beta 106.0990(10) _cell_angle_gamma 90.00 _cell_volume 1444.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6839 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 25.27 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.751 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 1.734 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6740 _exptl_absorpt_correction_T_max 0.8085 _exptl_absorpt_process_details SADABS _exptl_special_details ? _diffrn_ambient_temperature 173(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11495 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.27 _reflns_number_total 2624 _reflns_number_gt 2296 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0294P)^2^+0.9156P] 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 2624 _refine_ls_number_parameters 220 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0303 _refine_ls_R_factor_gt 0.0244 _refine_ls_wR_factor_ref 0.0621 _refine_ls_wR_factor_gt 0.0591 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.81247(3) 0.224633(12) 0.06118(2) 0.01655(9) Uani 1 1 d . . . O1 O 0.8210(2) 0.28961(8) 0.19912(14) 0.0226(3) Uani 1 1 d . . . O2 O 0.5260(2) 0.33025(8) 0.11724(14) 0.0282(4) Uani 1 1 d . . . O3 O 1.2108(2) 0.37447(8) 0.33912(14) 0.0236(3) Uani 1 1 d . . . O4 O 1.0774(2) 0.32335(8) 0.47749(13) 0.0227(3) Uani 1 1 d . . . O5 O 1.2484(3) 0.50280(8) -0.07498(14) 0.0325(4) Uani 1 1 d . . . N1 N 0.9469(2) 0.28473(9) -0.04255(16) 0.0177(4) Uani 1 1 d . . . N2 N 1.2535(2) 0.47026(9) 0.12625(16) 0.0177(4) Uani 1 1 d D . . H2N H 1.232(3) 0.4349(10) 0.172(2) 0.021 Uiso 1 1 d D . . N3 N 1.5194(2) 0.64619(9) 0.33695(16) 0.0178(4) Uani 1 1 d . . . C1 C 1.0435(3) 0.34224(11) 0.01240(19) 0.0176(4) Uani 1 1 d . . . H1 H 1.0655 0.3489 0.1017 0.021 Uiso 1 1 calc R . . C2 C 1.1122(3) 0.39217(11) -0.05633(19) 0.0169(4) Uani 1 1 d . . . C3 C 1.0790(3) 0.38141(11) -0.1873(2) 0.0191(5) Uani 1 1 d . . . H3 H 1.1222 0.4152 -0.2376 0.023 Uiso 1 1 calc R . . C4 C 0.9834(3) 0.32170(11) -0.2435(2) 0.0197(5) Uani 1 1 d . . . H4 H 0.9624 0.3132 -0.3322 0.024 Uiso 1 1 calc R . . C5 C 0.9189(3) 0.27459(11) -0.1685(2) 0.0195(5) Uani 1 1 d . . . H5 H 0.8522 0.2335 -0.2071 0.023 Uiso 1 1 calc R . . C6 C 1.4872(3) 0.64439(11) 0.20905(19) 0.0177(4) Uani 1 1 d . . . H6 H 1.5258 0.6841 0.1686 0.021 Uiso 1 1 calc R . . C7 C 1.4020(3) 0.58860(11) 0.13374(19) 0.0178(4) Uani 1 1 d . . . H7 H 1.3850 0.5895 0.0441 0.021 Uiso 1 1 calc R . . C8 C 1.3410(3) 0.53056(11) 0.19106(19) 0.0169(4) Uani 1 1 d . . . C9 C 1.3696(3) 0.53293(11) 0.32374(19) 0.0193(5) Uani 1 1 d . . . H9 H 1.3272 0.4950 0.3664 0.023 Uiso 1 1 calc R . . C10 C 1.4592(3) 0.59037(11) 0.3913(2) 0.0198(5) Uani 1 1 d . . . H10 H 1.4796 0.5907 0.4813 0.024 Uiso 1 1 calc R . . C11 C 1.2118(3) 0.45959(11) -0.0030(2) 0.0189(5) Uani 1 1 d . . . C12 C 0.6779(3) 0.32953(11) 0.20045(19) 0.0189(5) Uani 1 1 d . . . C13 C 0.7132(3) 0.37602(12) 0.3179(2) 0.0234(5) Uani 1 1 d . . . H13A H 0.7100 0.3463 0.3921 0.028 Uiso 1 1 calc R . . H13B H 0.6093 0.4113 0.3051 0.028 Uiso 1 1 calc R . . C14 C 0.9038(3) 0.41487(11) 0.3475(2) 0.0235(5) Uani 1 1 d . . . H14A H 0.9097 0.4417 0.2706 0.028 Uiso 1 1 calc R . . H14B H 0.9090 0.4496 0.4164 0.028 Uiso 1 1 calc R . . C15 C 1.0767(3) 0.36743(11) 0.38765(19) 0.0188(5) 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 0.01883(15) 0.01519(14) 0.01456(14) -0.00064(9) 0.00285(10) -0.00005(10) O1 0.0220(8) 0.0236(8) 0.0213(8) -0.0062(6) 0.0046(6) 0.0022(7) O2 0.0261(9) 0.0280(9) 0.0246(9) 0.0015(7) -0.0027(7) 0.0013(7) O3 0.0256(8) 0.0225(8) 0.0228(8) 0.0024(6) 0.0068(7) -0.0036(7) O4 0.0228(8) 0.0261(8) 0.0181(8) 0.0082(6) 0.0038(6) 0.0033(7) O5 0.0525(11) 0.0260(9) 0.0169(8) 0.0006(7) 0.0063(8) -0.0147(8) N1 0.0196(9) 0.0167(9) 0.0156(9) -0.0008(7) 0.0030(7) 0.0009(7) N2 0.0219(9) 0.0154(9) 0.0147(9) 0.0013(7) 0.0034(7) -0.0030(7) N3 0.0177(9) 0.0174(9) 0.0162(9) 0.0007(7) 0.0013(7) 0.0006(7) C1 0.0189(11) 0.0190(11) 0.0130(10) -0.0013(8) 0.0012(8) 0.0001(9) C2 0.0151(10) 0.0176(11) 0.0159(10) 0.0002(8) 0.0006(8) 0.0036(8) C3 0.0186(11) 0.0200(11) 0.0192(11) 0.0023(9) 0.0059(9) 0.0024(9) C4 0.0221(11) 0.0231(11) 0.0146(10) -0.0029(9) 0.0061(9) 0.0033(9) C5 0.0205(11) 0.0180(11) 0.0189(11) -0.0047(9) 0.0038(9) 0.0014(9) C6 0.0174(10) 0.0164(10) 0.0191(11) 0.0033(8) 0.0046(9) 0.0000(8) C7 0.0175(11) 0.0201(11) 0.0153(10) 0.0017(8) 0.0037(8) 0.0016(9) C8 0.0144(10) 0.0174(11) 0.0175(11) -0.0006(8) 0.0019(8) 0.0023(8) C9 0.0237(11) 0.0172(11) 0.0169(11) 0.0037(8) 0.0053(9) -0.0010(9) C10 0.0216(11) 0.0226(11) 0.0147(11) 0.0021(9) 0.0040(9) 0.0018(9) C11 0.0195(11) 0.0176(11) 0.0179(11) 0.0010(9) 0.0026(9) 0.0019(9) C12 0.0222(11) 0.0168(11) 0.0177(11) 0.0043(8) 0.0056(9) -0.0005(9) C13 0.0227(12) 0.0259(12) 0.0205(11) -0.0040(9) 0.0041(9) 0.0086(9) C14 0.0314(13) 0.0174(11) 0.0187(11) -0.0018(9) 0.0022(10) 0.0030(9) C15 0.0224(11) 0.0167(11) 0.0145(10) -0.0028(8) 0.0003(9) -0.0034(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.9274(14) . ? Zn1 O4 1.9328(14) 4_565 ? Zn1 N1 2.0360(17) . ? Zn1 N3 2.0438(17) 2_745 ? O1 C12 1.292(3) . ? O2 C12 1.224(2) . ? O3 C15 1.244(3) . ? O4 C15 1.284(2) . ? O4 Zn1 1.9327(14) 4_666 ? O5 C11 1.212(3) . ? N1 C1 1.342(3) . ? N1 C5 1.345(3) . ? N2 C11 1.371(3) . ? N2 C8 1.397(3) . ? N2 H2N 0.875(16) . ? N3 C10 1.341(3) . ? N3 C6 1.348(3) . ? N3 Zn1 2.0438(17) 2_755 ? C1 C2 1.382(3) . ? C1 H1 0.9500 . ? C2 C3 1.395(3) . ? C2 C11 1.500(3) . ? C3 C4 1.377(3) . ? C3 H3 0.9500 . ? C4 C5 1.376(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.373(3) . ? C6 H6 0.9500 . ? C7 C8 1.394(3) . ? C7 H7 0.9500 . ? C8 C9 1.403(3) . ? C9 C10 1.371(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C12 C13 1.514(3) . ? C13 C14 1.527(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.511(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? 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 O4 119.88(6) . 4_565 ? O1 Zn1 N1 99.38(7) . . ? O4 Zn1 N1 120.11(7) 4_565 . ? O1 Zn1 N3 98.76(7) . 2_745 ? O4 Zn1 N3 103.85(7) 4_565 2_745 ? N1 Zn1 N3 113.25(7) . 2_745 ? C12 O1 Zn1 121.89(13) . . ? C15 O4 Zn1 118.59(14) . 4_666 ? C1 N1 C5 118.89(18) . . ? C1 N1 Zn1 118.54(14) . . ? C5 N1 Zn1 121.84(14) . . ? C11 N2 C8 125.41(18) . . ? C11 N2 H2N 117.1(15) . . ? C8 N2 H2N 117.3(15) . . ? C10 N3 C6 116.91(18) . . ? C10 N3 Zn1 123.38(14) . 2_755 ? C6 N3 Zn1 119.08(14) . 2_755 ? N1 C1 C2 122.33(19) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C1 C2 C3 117.99(19) . . ? C1 C2 C11 125.31(19) . . ? C3 C2 C11 116.62(18) . . ? C4 C3 C2 119.8(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 118.66(19) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? N1 C5 C4 122.29(19) . . ? N1 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? N3 C6 C7 123.87(19) . . ? N3 C6 H6 118.1 . . ? C7 C6 H6 118.1 . . ? C6 C7 C8 118.86(19) . . ? C6 C7 H7 120.6 . . ? C8 C7 H7 120.6 . . ? C7 C8 N2 124.86(18) . . ? C7 C8 C9 117.52(19) . . ? N2 C8 C9 117.61(18) . . ? C10 C9 C8 119.43(19) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? N3 C10 C9 123.36(19) . . ? N3 C10 H10 118.3 . . ? C9 C10 H10 118.3 . . ? O5 C11 N2 122.7(2) . . ? O5 C11 C2 119.32(19) . . ? N2 C11 C2 117.95(18) . . ? O2 C12 O1 124.7(2) . . ? O2 C12 C13 121.82(19) . . ? O1 C12 C13 113.48(18) . . ? C12 C13 C14 112.83(18) . . ? C12 C13 H13A 109.0 . . ? C14 C13 H13A 109.0 . . ? C12 C13 H13B 109.0 . . ? C14 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C15 C14 C13 114.69(18) . . ? C15 C14 H14A 108.6 . . ? C13 C14 H14A 108.6 . . ? C15 C14 H14B 108.6 . . ? C13 C14 H14B 108.6 . . ? H14A C14 H14B 107.6 . . ? O3 C15 O4 123.84(19) . . ? O3 C15 C14 120.54(19) . . ? O4 C15 C14 115.52(19) . . ? 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 O4 Zn1 O1 C12 -35.22(18) 4_565 . . . ? N1 Zn1 O1 C12 97.72(16) . . . . ? N3 Zn1 O1 C12 -146.80(16) 2_745 . . . ? O1 Zn1 N1 C1 14.43(16) . . . . ? O4 Zn1 N1 C1 147.23(14) 4_565 . . . ? N3 Zn1 N1 C1 -89.39(16) 2_745 . . . ? O1 Zn1 N1 C5 -155.70(16) . . . . ? O4 Zn1 N1 C5 -22.91(18) 4_565 . . . ? N3 Zn1 N1 C5 100.47(16) 2_745 . . . ? C5 N1 C1 C2 1.3(3) . . . . ? Zn1 N1 C1 C2 -169.16(16) . . . . ? N1 C1 C2 C3 -0.2(3) . . . . ? N1 C1 C2 C11 176.45(19) . . . . ? C1 C2 C3 C4 -1.2(3) . . . . ? C11 C2 C3 C4 -178.13(18) . . . . ? C2 C3 C4 C5 1.5(3) . . . . ? C1 N1 C5 C4 -1.0(3) . . . . ? Zn1 N1 C5 C4 169.10(16) . . . . ? C3 C4 C5 N1 -0.4(3) . . . . ? C10 N3 C6 C7 -1.7(3) . . . . ? Zn1 N3 C6 C7 169.55(16) 2_755 . . . ? N3 C6 C7 C8 1.3(3) . . . . ? C6 C7 C8 N2 -179.59(19) . . . . ? C6 C7 C8 C9 0.4(3) . . . . ? C11 N2 C8 C7 -1.2(3) . . . . ? C11 N2 C8 C9 178.84(19) . . . . ? C7 C8 C9 C10 -1.6(3) . . . . ? N2 C8 C9 C10 178.39(19) . . . . ? C6 N3 C10 C9 0.4(3) . . . . ? Zn1 N3 C10 C9 -170.45(16) 2_755 . . . ? C8 C9 C10 N3 1.2(3) . . . . ? C8 N2 C11 O5 0.1(3) . . . . ? C8 N2 C11 C2 -178.28(18) . . . . ? C1 C2 C11 O5 -172.5(2) . . . . ? C3 C2 C11 O5 4.2(3) . . . . ? C1 C2 C11 N2 6.0(3) . . . . ? C3 C2 C11 N2 -177.32(18) . . . . ? Zn1 O1 C12 O2 0.3(3) . . . . ? Zn1 O1 C12 C13 179.37(13) . . . . ? O2 C12 C13 C14 -132.9(2) . . . . ? O1 C12 C13 C14 47.9(2) . . . . ? C12 C13 C14 C15 -67.0(2) . . . . ? Zn1 O4 C15 O3 10.0(3) 4_666 . . . ? Zn1 O4 C15 C14 -166.61(13) 4_666 . . . ? C13 C14 C15 O3 132.6(2) . . . . ? C13 C14 C15 O4 -50.7(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 N2 H2N O3 0.875(16) 2.187(17) 3.025(2) 160(2) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.325 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.058