# 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_upc1 #TrackingRef 'upc1-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H12 N2 O5 Zn' _chemical_formula_weight 401.67 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 '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 13.629(3) _cell_length_b 24.248(5) _cell_length_c 14.286(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.645(3) _cell_angle_gamma 90.00 _cell_volume 4567.8(17) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2723 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 24.29 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.168 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 1.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8613 _exptl_absorpt_correction_T_max 0.8980 _exptl_absorpt_process_details 'APEX2 Software Suite (Bruker,2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11113 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0600 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4009 _reflns_number_gt 2961 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 Software Suite (Bruker,2005)' _computing_cell_refinement 'APEX2 Software Suite' _computing_data_reduction 'APEX2 Software Suite' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2008)' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0802P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4009 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1278 _refine_ls_wR_factor_gt 0.1201 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 0.961 _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 0.04365(3) 0.146124(15) 0.38410(2) 0.03244(16) Uani 1 1 d . . . O1 O 0.13397(18) 0.18109(10) 0.30554(17) 0.0452(6) Uani 1 1 d . . . O2 O 0.06012(19) 0.20538(10) 0.15222(16) 0.0453(6) Uani 1 1 d . . . O3 O 0.37480(18) 0.32576(11) 0.49056(15) 0.0453(6) Uani 1 1 d . . . O4 O 0.48606(19) 0.35924(10) 0.41567(17) 0.0449(6) Uani 1 1 d . . . O5 O 0.3241(2) 0.32096(13) 0.06153(16) 0.0658(9) Uani 1 1 d . . . H5 H 0.3852 0.3207 0.0657 0.099 Uiso 1 1 d R . . N1 N 0.1193(2) 0.06994(12) 0.3784(2) 0.0413(7) Uani 1 1 d . . . N2 N -0.0722(2) 0.08460(12) 0.37860(19) 0.0395(7) Uani 1 1 d . . . C1 C 0.4069(3) 0.33324(14) 0.4157(2) 0.0353(8) Uani 1 1 d . . . C2 C 0.3430(3) 0.31027(14) 0.3223(2) 0.0355(8) Uani 1 1 d . . . C3 C 0.2681(3) 0.27183(14) 0.3210(2) 0.0369(8) Uani 1 1 d . . . H3 H 0.2563 0.2595 0.3788 0.044 Uiso 1 1 calc R . . C4 C 0.2104(3) 0.25153(14) 0.2335(2) 0.0372(8) Uani 1 1 d . . . C5 C 0.1283(3) 0.20932(14) 0.2311(2) 0.0382(8) Uani 1 1 d . . . C6 C 0.2296(3) 0.26857(16) 0.1472(2) 0.0445(9) Uani 1 1 d . . . H6 H 0.1905 0.2551 0.0887 0.053 Uiso 1 1 calc R . . C7 C 0.3073(3) 0.30572(16) 0.1484(2) 0.0453(9) Uani 1 1 d . . . C8 C 0.3627(3) 0.32661(15) 0.2348(2) 0.0439(9) Uani 1 1 d . . . H8 H 0.4141 0.3519 0.2353 0.053 Uiso 1 1 calc R . . C9 C 0.2166(3) 0.06522(17) 0.3807(3) 0.0570(11) Uani 1 1 d . . . H9 H 0.2541 0.0972 0.3804 0.068 Uiso 1 1 calc R . . C10 C 0.2649(3) 0.0152(2) 0.3834(3) 0.0664(12) Uani 1 1 d . . . H10 H 0.3336 0.0134 0.3856 0.080 Uiso 1 1 calc R . . C11 C 0.2097(4) -0.03160(19) 0.3829(3) 0.0680(12) Uani 1 1 d . . . H11 H 0.2406 -0.0659 0.3848 0.082 Uiso 1 1 calc R . . C12 C 0.1086(3) -0.02812(16) 0.3796(3) 0.0546(10) Uani 1 1 d . . . H12 H 0.0700 -0.0599 0.3783 0.066 Uiso 1 1 calc R . . C13 C 0.0647(3) 0.02349(15) 0.3781(2) 0.0416(9) Uani 1 1 d . . . C14 C -0.0436(3) 0.03202(15) 0.3762(2) 0.0415(9) Uani 1 1 d . . . C15 C -0.1121(3) -0.01101(18) 0.3732(3) 0.0582(11) Uani 1 1 d . . . H15 H -0.0909 -0.0474 0.3723 0.070 Uiso 1 1 calc R . . C16 C -0.2111(4) 0.0007(2) 0.3716(3) 0.0707(13) Uani 1 1 d . . . H16 H -0.2579 -0.0276 0.3688 0.085 Uiso 1 1 calc R . . C17 C -0.2396(3) 0.0545(2) 0.3743(3) 0.0651(12) Uani 1 1 d . . . H17 H -0.3062 0.0634 0.3734 0.078 Uiso 1 1 calc R . . C18 C -0.1692(3) 0.09506(18) 0.3783(3) 0.0502(10) Uani 1 1 d . . . H18 H -0.1893 0.1316 0.3810 0.060 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 0.0388(3) 0.0308(2) 0.0253(2) 0.00052(15) 0.00342(17) -0.00120(17) O1 0.0520(15) 0.0445(15) 0.0393(14) 0.0084(12) 0.0122(12) -0.0078(12) O2 0.0509(14) 0.0439(15) 0.0356(14) 0.0009(11) 0.0008(12) -0.0146(12) O3 0.0509(15) 0.0599(17) 0.0221(12) -0.0035(11) 0.0035(11) -0.0110(13) O4 0.0479(15) 0.0454(15) 0.0396(14) -0.0051(11) 0.0077(12) -0.0123(12) O5 0.0751(19) 0.096(2) 0.0268(13) 0.0017(14) 0.0139(13) -0.0412(18) N1 0.0470(17) 0.0362(17) 0.0416(17) 0.0060(13) 0.0130(14) 0.0010(14) N2 0.0480(18) 0.0390(18) 0.0289(15) 0.0007(12) 0.0050(13) -0.0020(14) C1 0.047(2) 0.0269(18) 0.0297(18) 0.0012(14) 0.0054(16) 0.0036(16) C2 0.0431(19) 0.037(2) 0.0241(17) 0.0001(14) 0.0043(14) -0.0027(16) C3 0.048(2) 0.038(2) 0.0246(17) 0.0011(14) 0.0092(15) -0.0042(16) C4 0.048(2) 0.038(2) 0.0242(17) -0.0006(14) 0.0068(15) -0.0070(16) C5 0.048(2) 0.035(2) 0.035(2) -0.0025(15) 0.0154(17) -0.0043(16) C6 0.057(2) 0.050(2) 0.0253(18) -0.0038(15) 0.0069(16) -0.0171(19) C7 0.060(2) 0.052(2) 0.0230(18) 0.0014(15) 0.0096(17) -0.0169(19) C8 0.054(2) 0.041(2) 0.035(2) 0.0008(16) 0.0103(17) -0.0172(18) C9 0.053(2) 0.048(3) 0.073(3) 0.007(2) 0.021(2) -0.003(2) C10 0.052(2) 0.066(3) 0.084(3) 0.008(2) 0.023(2) 0.010(2) C11 0.082(3) 0.049(3) 0.077(3) 0.006(2) 0.027(3) 0.020(2) C12 0.076(3) 0.036(2) 0.055(2) 0.0012(18) 0.023(2) 0.001(2) C13 0.064(2) 0.034(2) 0.0271(18) 0.0032(14) 0.0124(17) 0.0003(18) C14 0.055(2) 0.043(2) 0.0242(17) 0.0004(15) 0.0062(16) -0.0098(18) C15 0.077(3) 0.045(3) 0.053(2) -0.0008(19) 0.016(2) -0.012(2) C16 0.066(3) 0.074(4) 0.074(3) -0.005(2) 0.021(2) -0.029(3) C17 0.047(2) 0.085(4) 0.062(3) 0.005(2) 0.011(2) -0.010(2) C18 0.049(2) 0.057(3) 0.044(2) 0.0008(18) 0.0097(18) 0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 1.975(2) 7_556 ? Zn1 O2 1.991(2) 2 ? Zn1 O1 2.047(2) . ? Zn1 N1 2.127(3) . ? Zn1 N2 2.159(3) . ? O1 C5 1.251(4) . ? O2 C5 1.270(4) . ? O2 Zn1 1.991(2) 2 ? O3 C1 1.266(4) . ? O3 Zn1 1.975(2) 7_556 ? O4 C1 1.250(4) . ? O5 C7 1.369(4) . ? O5 H5 0.8199 . ? N1 C9 1.324(5) . ? N1 C13 1.349(5) . ? N2 C14 1.336(5) . ? N2 C18 1.346(5) . ? C1 C2 1.505(5) . ? C2 C3 1.379(5) . ? C2 C8 1.401(4) . ? C3 C4 1.388(4) . ? C3 H3 0.9300 . ? C4 C6 1.386(5) . ? C4 C5 1.511(5) . ? C6 C7 1.387(5) . ? C6 H6 0.9300 . ? C7 C8 1.371(5) . ? C8 H8 0.9300 . ? C9 C10 1.375(6) . ? C9 H9 0.9300 . ? C10 C11 1.361(6) . ? C10 H10 0.9300 . ? C11 C12 1.370(6) . ? C11 H11 0.9300 . ? C12 C13 1.385(5) . ? C12 H12 0.9300 . ? C13 C14 1.484(5) . ? C14 C15 1.394(5) . ? C15 C16 1.372(6) . ? C15 H15 0.9300 . ? C16 C17 1.365(6) . ? C16 H16 0.9300 . ? C17 C18 1.365(6) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 O2 100.78(10) 7_556 2 ? O3 Zn1 O1 94.33(10) 7_556 . ? O2 Zn1 O1 92.53(10) 2 . ? O3 Zn1 N1 99.63(11) 7_556 . ? O2 Zn1 N1 159.42(11) 2 . ? O1 Zn1 N1 88.54(10) . . ? O3 Zn1 N2 120.68(10) 7_556 . ? O2 Zn1 N2 91.40(12) 2 . ? O1 Zn1 N2 143.28(10) . . ? N1 Zn1 N2 75.84(11) . . ? C5 O1 Zn1 140.9(2) . . ? C5 O2 Zn1 126.7(2) . 2 ? C1 O3 Zn1 118.7(2) . 7_556 ? C7 O5 H5 109.3 . . ? C9 N1 C13 118.4(3) . . ? C9 N1 Zn1 124.5(3) . . ? C13 N1 Zn1 117.0(2) . . ? C14 N2 C18 118.2(3) . . ? C14 N2 Zn1 116.4(2) . . ? C18 N2 Zn1 125.4(3) . . ? O4 C1 O3 123.8(3) . . ? O4 C1 C2 119.5(3) . . ? O3 C1 C2 116.7(3) . . ? C3 C2 C8 119.2(3) . . ? C3 C2 C1 121.5(3) . . ? C8 C2 C1 119.2(3) . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C6 C4 C3 120.2(3) . . ? C6 C4 C5 119.2(3) . . ? C3 C4 C5 120.6(3) . . ? O1 C5 O2 126.0(3) . . ? O1 C5 C4 117.7(3) . . ? O2 C5 C4 116.3(3) . . ? C4 C6 C7 119.9(3) . . ? C4 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? O5 C7 C8 122.4(3) . . ? O5 C7 C6 117.8(3) . . ? C8 C7 C6 119.8(3) . . ? C7 C8 C2 120.8(3) . . ? C7 C8 H8 119.6 . . ? C2 C8 H8 119.6 . . ? N1 C9 C10 123.1(4) . . ? N1 C9 H9 118.5 . . ? C10 C9 H9 118.5 . . ? C11 C10 C9 118.4(4) . . ? C11 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? C10 C11 C12 119.9(4) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C13 118.9(4) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? N1 C13 C12 121.3(4) . . ? N1 C13 C14 115.4(3) . . ? C12 C13 C14 123.3(4) . . ? N2 C14 C15 121.2(4) . . ? N2 C14 C13 115.3(3) . . ? C15 C14 C13 123.5(4) . . ? C16 C15 C14 119.6(4) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C17 C16 C15 118.8(4) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C18 C17 C16 119.2(4) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? N2 C18 C17 122.9(4) . . ? N2 C18 H18 118.5 . . ? C17 C18 H18 118.5 . . ? 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 C5 -132.3(4) 7_556 . . . ? O2 Zn1 O1 C5 -31.3(4) 2 . . . ? N1 Zn1 O1 C5 128.1(4) . . . . ? N2 Zn1 O1 C5 64.5(4) . . . . ? O3 Zn1 N1 C9 -59.1(3) 7_556 . . . ? O2 Zn1 N1 C9 128.4(4) 2 . . . ? O1 Zn1 N1 C9 35.1(3) . . . . ? N2 Zn1 N1 C9 -178.5(3) . . . . ? O3 Zn1 N1 C13 117.0(2) 7_556 . . . ? O2 Zn1 N1 C13 -55.6(4) 2 . . . ? O1 Zn1 N1 C13 -148.9(2) . . . . ? N2 Zn1 N1 C13 -2.4(2) . . . . ? O3 Zn1 N2 C14 -91.8(2) 7_556 . . . ? O2 Zn1 N2 C14 164.8(2) 2 . . . ? O1 Zn1 N2 C14 68.6(3) . . . . ? N1 Zn1 N2 C14 1.1(2) . . . . ? O3 Zn1 N2 C18 87.5(3) 7_556 . . . ? O2 Zn1 N2 C18 -15.9(3) 2 . . . ? O1 Zn1 N2 C18 -112.0(3) . . . . ? N1 Zn1 N2 C18 -179.6(3) . . . . ? Zn1 O3 C1 O4 -2.6(5) 7_556 . . . ? Zn1 O3 C1 C2 179.0(2) 7_556 . . . ? O4 C1 C2 C3 165.9(3) . . . . ? O3 C1 C2 C3 -15.6(5) . . . . ? O4 C1 C2 C8 -11.4(5) . . . . ? O3 C1 C2 C8 167.0(3) . . . . ? C8 C2 C3 C4 -2.7(5) . . . . ? C1 C2 C3 C4 179.9(3) . . . . ? C2 C3 C4 C6 1.8(5) . . . . ? C2 C3 C4 C5 179.9(3) . . . . ? Zn1 O1 C5 O2 -37.0(6) . . . . ? Zn1 O1 C5 C4 144.0(3) . . . . ? Zn1 O2 C5 O1 -10.7(5) 2 . . . ? Zn1 O2 C5 C4 168.2(2) 2 . . . ? C6 C4 C5 O1 156.3(3) . . . . ? C3 C4 C5 O1 -21.8(5) . . . . ? C6 C4 C5 O2 -22.8(5) . . . . ? C3 C4 C5 O2 159.2(3) . . . . ? C3 C4 C6 C7 0.5(6) . . . . ? C5 C4 C6 C7 -177.6(3) . . . . ? C4 C6 C7 O5 179.4(4) . . . . ? C4 C6 C7 C8 -1.9(6) . . . . ? O5 C7 C8 C2 179.6(4) . . . . ? C6 C7 C8 C2 1.0(6) . . . . ? C3 C2 C8 C7 1.3(6) . . . . ? C1 C2 C8 C7 178.8(3) . . . . ? C13 N1 C9 C10 -0.5(6) . . . . ? Zn1 N1 C9 C10 175.5(3) . . . . ? N1 C9 C10 C11 0.6(7) . . . . ? C9 C10 C11 C12 0.1(7) . . . . ? C10 C11 C12 C13 -0.9(7) . . . . ? C9 N1 C13 C12 -0.4(5) . . . . ? Zn1 N1 C13 C12 -176.6(3) . . . . ? C9 N1 C13 C14 179.6(3) . . . . ? Zn1 N1 C13 C14 3.3(4) . . . . ? C11 C12 C13 N1 1.0(5) . . . . ? C11 C12 C13 C14 -178.9(4) . . . . ? C18 N2 C14 C15 0.3(5) . . . . ? Zn1 N2 C14 C15 179.6(3) . . . . ? C18 N2 C14 C13 -179.2(3) . . . . ? Zn1 N2 C14 C13 0.2(4) . . . . ? N1 C13 C14 N2 -2.3(4) . . . . ? C12 C13 C14 N2 177.7(3) . . . . ? N1 C13 C14 C15 178.3(3) . . . . ? C12 C13 C14 C15 -1.7(5) . . . . ? N2 C14 C15 C16 0.7(6) . . . . ? C13 C14 C15 C16 180.0(4) . . . . ? C14 C15 C16 C17 -0.8(6) . . . . ? C15 C16 C17 C18 0.1(7) . . . . ? C14 N2 C18 C17 -1.0(5) . . . . ? Zn1 N2 C18 C17 179.7(3) . . . . ? C16 C17 C18 N2 0.8(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 O5 H5 O4 0.82 1.95 2.690(4) 150.5 2_655 C12 H12 O4 0.93 2.40 3.309(5) 166.4 3_445 C15 H15 O4 0.93 2.51 3.413(5) 165.0 3_445 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.611 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.084 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 -0.008 869 102 ' ' 2 0.500 1.000 0.133 869 102 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 934992' ####################################################################### # # 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_upc2 #TrackingRef 'upc1-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H10 N2 Ni O7' _chemical_formula_weight 424.99 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.163(6) _cell_length_b 10.737(6) _cell_length_c 11.300(6) _cell_angle_alpha 74.521(9) _cell_angle_beta 89.840(9) _cell_angle_gamma 68.492(9) _cell_volume 1099.3(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3113 _cell_measurement_theta_max 27.3 _cell_measurement_theta_min 2.4 _exptl_crystal_description ' block' _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.919 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8376 _exptl_absorpt_correction_T_max 0.9137 _exptl_absorpt_process_details 'APEX2 Software Suite (Bruker,2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5354 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0568 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3780 _reflns_number_gt 3186 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 Software Suite (Bruker,2005)' _computing_cell_refinement 'APEX2 Software Suite' _computing_data_reduction 'APEX2 Software Suite' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2008)' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.1157P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3780 _refine_ls_number_parameters 279 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1670 _refine_ls_wR_factor_gt 0.1613 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.061 _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 Ni1 Ni 1.45363(4) 0.27041(5) 0.10636(4) 0.0226(2) Uani 1 1 d . . . O1 O 0.6461(3) 0.0961(3) 0.1451(3) 0.0321(6) Uani 1 1 d . . . O1W O 1.3018(3) 0.4698(3) 0.0598(3) 0.0351(7) Uani 1 1 d . . . H1WA H 1.2174 0.4710 0.0405 0.053 Uiso 1 1 d R . . H1WB H 1.3225 0.5244 -0.0041 0.053 Uiso 1 1 d R . . O2 O 0.6513(3) 0.3065(3) 0.0900(2) 0.0299(6) Uani 1 1 d . . . O2W O 0.9949(5) -0.3787(5) 0.1933(5) 0.0975(15) Uani 1 1 d . . . O3 O 1.1622(3) -0.2362(3) 0.2119(5) 0.0758(13) Uani 1 1 d . . . H3A H 1.1058 -0.2744 0.2108 0.114 Uiso 1 1 calc R . . O4 O 1.1227(3) 0.3502(4) 0.0426(4) 0.0710(13) Uani 1 1 d . . . O5 O 1.3172(3) 0.1703(3) 0.1403(2) 0.0308(6) Uani 1 1 d . . . N1 N 1.4468(3) 0.2729(4) -0.0800(3) 0.0316(8) Uani 1 1 d . . . N2 N 1.4564(4) 0.2709(4) -0.7051(2) 0.0348(8) Uani 1 1 d G . . C15A C 1.5742(5) 0.2681(10) -0.6407(4) 0.046(3) Uani 0.30 1 d PGU . . C16A C 1.5708(5) 0.2685(11) -0.5178(4) 0.050(3) Uani 0.30 1 d PGU . . C12 C 1.4496(5) 0.2716(5) -0.4594(2) 0.0405(10) Uani 1 1 d G . . C13A C 1.3318(5) 0.2744(11) -0.5238(4) 0.065(4) Uani 0.30 1 d PGU . . C14A C 1.3352(5) 0.2740(11) -0.6467(4) 0.062(4) Uani 0.30 1 d PGU . . C1 C 0.7155(4) 0.1745(4) 0.1211(3) 0.0270(8) Uani 1 1 d . . . C2 C 0.8756(4) 0.1093(4) 0.1334(4) 0.0305(9) Uani 1 1 d . . . C3 C 0.9543(4) 0.1942(4) 0.1123(4) 0.0347(9) Uani 1 1 d . . . H3 H 0.9082 0.2909 0.0887 0.042 Uiso 1 1 calc R . . C4 C 1.1024(4) 0.1330(4) 0.1268(4) 0.0341(9) Uani 1 1 d . . . C5 C 1.1867(4) 0.2253(4) 0.1011(4) 0.0368(10) Uani 1 1 d . . . C6 C 1.1700(4) -0.0125(5) 0.1620(4) 0.0420(11) Uani 1 1 d . . . H6 H 1.2687 -0.0538 0.1739 0.050 Uiso 1 1 calc R . . C7 C 1.0906(4) -0.0953(4) 0.1791(5) 0.0429(11) Uani 1 1 d . . . C8 C 0.9428(4) -0.0339(4) 0.1643(4) 0.0393(10) Uani 1 1 d . . . H8 H 0.8894 -0.0896 0.1753 0.047 Uiso 1 1 calc R . . C9 C 1.4195(5) 0.1760(4) -0.1161(4) 0.0369(10) Uani 1 1 d . . . H9 H 1.4004 0.1074 -0.0573 0.044 Uiso 1 1 calc R . . C10 C 1.4183(5) 0.1728(5) -0.2375(4) 0.0407(10) Uani 1 1 d . . . H10 H 1.3995 0.1025 -0.2585 0.049 Uiso 1 1 calc R . . C11 C 1.4448(5) 0.2729(5) -0.3272(4) 0.0375(10) Uani 1 1 d . . . C13 C 1.5192(10) 0.1564(8) -0.4902(7) 0.067(2) Uani 0.70 1 d PU . . C14 C 1.5217(10) 0.1605(8) -0.6132(6) 0.065(2) Uani 0.70 1 d PU . . C15 C 1.3692(7) 0.3880(8) -0.6743(6) 0.0485(16) Uani 0.70 1 d PU . . C16 C 1.3628(8) 0.3916(8) -0.5521(6) 0.0513(16) Uani 0.70 1 d PU . . C17 C 1.4693(8) 0.3753(6) -0.2898(5) 0.0718(19) Uani 1 1 d . . . H17 H 1.4846 0.4472 -0.3474 0.086 Uiso 1 1 calc R . . C18 C 1.4710(7) 0.3710(6) -0.1662(4) 0.0609(16) Uani 1 1 d . . . H18 H 1.4899 0.4399 -0.1426 0.073 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 Ni1 0.0174(3) 0.0314(3) 0.0210(3) -0.0053(2) 0.00168(18) -0.0131(2) O1 0.0192(13) 0.0329(15) 0.0461(17) -0.0053(13) 0.0023(11) -0.0161(12) O1W 0.0266(14) 0.0352(16) 0.0411(17) -0.0030(13) 0.0025(12) -0.0146(12) O2 0.0201(12) 0.0328(16) 0.0361(15) -0.0050(12) 0.0015(11) -0.0128(12) O2W 0.101(4) 0.090(4) 0.120(4) -0.028(3) 0.004(3) -0.060(3) O3 0.0308(17) 0.035(2) 0.153(4) -0.016(2) -0.001(2) -0.0105(15) O4 0.0303(17) 0.039(2) 0.128(4) 0.011(2) -0.0160(19) -0.0192(15) O5 0.0182(13) 0.0379(16) 0.0363(15) -0.0052(12) 0.0016(11) -0.0146(12) N1 0.0295(17) 0.041(2) 0.0259(17) -0.0064(15) 0.0022(13) -0.0180(15) N2 0.0364(18) 0.045(2) 0.0272(18) -0.0088(16) 0.0037(14) -0.0211(17) C15A 0.054(6) 0.064(7) 0.023(5) -0.015(5) 0.001(5) -0.023(5) C16A 0.053(6) 0.069(7) 0.024(5) -0.011(5) 0.000(5) -0.022(6) C12 0.058(3) 0.042(3) 0.026(2) -0.0074(19) 0.0048(19) -0.026(2) C13A 0.068(7) 0.087(7) 0.037(6) -0.017(6) 0.000(5) -0.028(6) C14A 0.067(7) 0.086(7) 0.032(6) -0.019(6) 0.007(5) -0.027(6) C1 0.0212(18) 0.031(2) 0.029(2) -0.0040(16) 0.0017(15) -0.0127(16) C2 0.0188(18) 0.036(2) 0.038(2) -0.0045(18) 0.0001(15) -0.0157(17) C3 0.0223(19) 0.030(2) 0.050(3) -0.0051(19) 0.0004(17) -0.0114(17) C4 0.0179(18) 0.040(2) 0.045(2) -0.0066(19) 0.0015(16) -0.0154(17) C5 0.0202(19) 0.040(3) 0.049(3) -0.007(2) 0.0007(17) -0.0149(18) C6 0.0199(19) 0.043(3) 0.060(3) -0.010(2) -0.0008(18) -0.0117(18) C7 0.024(2) 0.030(2) 0.068(3) -0.004(2) 0.0014(19) -0.0093(18) C8 0.025(2) 0.034(2) 0.059(3) -0.004(2) 0.0019(18) -0.0178(18) C9 0.048(2) 0.038(2) 0.032(2) -0.0099(19) 0.0096(18) -0.025(2) C10 0.061(3) 0.046(3) 0.030(2) -0.018(2) 0.009(2) -0.032(2) C11 0.052(3) 0.042(3) 0.025(2) -0.0096(19) 0.0037(18) -0.026(2) C13 0.093(5) 0.051(4) 0.030(3) -0.011(3) -0.003(3) 0.001(4) C14 0.093(5) 0.043(4) 0.032(3) -0.003(3) -0.002(3) 0.001(4) C15 0.055(4) 0.057(4) 0.029(3) -0.017(3) 0.006(3) -0.013(3) C16 0.067(4) 0.051(4) 0.028(3) -0.012(3) 0.003(3) -0.013(3) C17 0.145(6) 0.073(4) 0.031(3) -0.015(3) 0.019(3) -0.080(4) C18 0.112(5) 0.073(4) 0.031(3) -0.018(2) 0.013(3) -0.071(4) _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 Ni1 O5 2.024(3) . ? Ni1 O1W 2.055(3) . ? Ni1 O1 2.098(3) 1_655 ? Ni1 N1 2.100(3) . ? Ni1 N2 2.132(3) 1_556 ? Ni1 O2 2.179(3) 1_655 ? Ni1 C1 2.464(4) 1_655 ? O1 C1 1.262(4) . ? O1 Ni1 2.098(3) 1_455 ? O1W H1WA 0.8801 . ? O1W H1WB 0.8789 . ? O2 C1 1.271(5) . ? O2 Ni1 2.179(3) 1_455 ? O3 C7 1.361(5) . ? O3 H3A 0.8200 . ? O4 C5 1.244(5) . ? O5 C5 1.262(5) . ? N1 C18 1.327(5) . ? N1 C9 1.329(5) . ? N2 C14 1.301(8) . ? N2 C15 1.380(7) . ? N2 C15A 1.3900 . ? N2 C14A 1.3900 . ? N2 Ni1 2.132(3) 1_554 ? C15A C16A 1.3900 . ? C15A C14 1.406(12) . ? C15A C15 1.980(9) . ? C15A C13 2.011(10) . ? C16A C12 1.3900 . ? C16A C13 1.443(12) . ? C16A C14 1.962(10) . ? C16A C16 2.012(10) . ? C12 C13 1.318(9) . ? C12 C13A 1.3900 . ? C12 C16 1.410(8) . ? C12 C11 1.498(5) . ? C13A C16 1.364(11) . ? C13A C14A 1.3900 . ? C13A C13 1.831(10) . ? C13A C15 1.937(9) . ? C14A C15 1.349(11) . ? C14A C14 1.812(10) . ? C14A C16 1.948(10) . ? C1 C2 1.507(5) . ? C1 Ni1 2.464(4) 1_455 ? C2 C8 1.377(6) . ? C2 C3 1.395(5) . ? C3 C4 1.394(5) . ? C3 H3 0.9300 . ? C4 C6 1.398(6) . ? C4 C5 1.507(5) . ? C6 C7 1.382(6) . ? C6 H6 0.9300 . ? C7 C8 1.391(6) . ? C8 H8 0.9300 . ? C9 C10 1.380(6) . ? C9 H9 0.9300 . ? C10 C11 1.373(6) . ? C10 H10 0.9300 . ? C11 C17 1.378(6) . ? C13 C14 1.380(10) . ? C15 C16 1.392(9) . ? C17 C18 1.385(7) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Ni1 O1W 96.54(12) . . ? O5 Ni1 O1 99.05(11) . 1_655 ? O1W Ni1 O1 164.41(10) . 1_655 ? O5 Ni1 N1 91.50(12) . . ? O1W Ni1 N1 89.96(12) . . ? O1 Ni1 N1 89.97(12) 1_655 . ? O5 Ni1 N2 88.14(11) . 1_556 ? O1W Ni1 N2 89.03(12) . 1_556 ? O1 Ni1 N2 91.14(12) 1_655 1_556 ? N1 Ni1 N2 178.88(12) . 1_556 ? O5 Ni1 O2 160.82(11) . 1_655 ? O1W Ni1 O2 102.61(11) . 1_655 ? O1 Ni1 O2 61.80(10) 1_655 1_655 ? N1 Ni1 O2 89.52(11) . 1_655 ? N2 Ni1 O2 91.17(11) 1_556 1_655 ? O5 Ni1 C1 129.85(12) . 1_655 ? O1W Ni1 C1 133.60(12) . 1_655 ? O1 Ni1 C1 30.81(11) 1_655 1_655 ? N1 Ni1 C1 89.41(12) . 1_655 ? N2 Ni1 C1 91.63(13) 1_556 1_655 ? O2 Ni1 C1 30.99(11) 1_655 1_655 ? C1 O1 Ni1 90.8(2) . 1_455 ? Ni1 O1W H1WA 111.4 . . ? Ni1 O1W H1WB 111.1 . . ? H1WA O1W H1WB 107.6 . . ? C1 O2 Ni1 87.0(2) . 1_455 ? C7 O3 H3A 109.5 . . ? C5 O5 Ni1 124.4(3) . . ? C18 N1 C9 117.4(4) . . ? C18 N1 Ni1 121.1(3) . . ? C9 N1 Ni1 121.5(3) . . ? C14 N2 C15 116.0(5) . . ? C14 N2 C15A 62.9(5) . . ? C15 N2 C15A 91.3(4) . . ? C14 N2 C14A 84.6(5) . . ? C15 N2 C14A 58.3(5) . . ? C15A N2 C14A 120.0 . . ? C14 N2 Ni1 123.9(4) . 1_554 ? C15 N2 Ni1 119.4(3) . 1_554 ? C15A N2 Ni1 122.17(18) . 1_554 ? C14A N2 Ni1 117.83(18) . 1_554 ? C16A C15A N2 120.0 . . ? C16A C15A C14 89.1(3) . . ? N2 C15A C14 55.5(4) . . ? C16A C15A C15 90.0(2) . . ? N2 C15A C15 44.2(3) . . ? C14 C15A C15 82.5(4) . . ? C16A C15A C13 45.9(3) . . ? N2 C15A C13 86.8(3) . . ? C14 C15A C13 43.3(4) . . ? C15 C15A C13 85.3(3) . . ? C15A C16A C12 120.0 . . ? C15A C16A C13 90.4(3) . . ? C12 C16A C13 55.4(4) . . ? C15A C16A C14 45.8(3) . . ? C12 C16A C14 86.4(3) . . ? C13 C16A C14 44.7(4) . . ? C15A C16A C16 90.0(2) . . ? C12 C16A C16 44.4(3) . . ? C13 C16A C16 83.9(4) . . ? C14 C16A C16 85.0(3) . . ? C13 C12 C16A 64.3(5) . . ? C13 C12 C13A 85.0(5) . . ? C16A C12 C13A 120.0 . . ? C13 C12 C16 118.7(5) . . ? C16A C12 C16 91.9(5) . . ? C13A C12 C16 58.3(5) . . ? C13 C12 C11 121.7(5) . . ? C16A C12 C11 120.3(3) . . ? C13A C12 C11 119.7(3) . . ? C16 C12 C11 119.1(4) . . ? C16 C13A C14A 90.0(3) . . ? C16 C13A C12 61.6(4) . . ? C14A C13A C12 120.0 . . ? C16 C13A C13 93.4(5) . . ? C14A C13A C13 90.3(2) . . ? C12 C13A C13 45.8(3) . . ? C16 C13A C15 45.9(4) . . ? C14A C13A C15 44.1(3) . . ? C12 C13A C15 90.9(3) . . ? C13 C13A C15 91.7(3) . . ? C15 C14A C13A 90.0(3) . . ? C15 C14A N2 60.5(4) . . ? C13A C14A N2 120.0 . . ? C15 C14A C14 90.8(4) . . ? C13A C14A C14 89.3(3) . . ? N2 C14A C14 45.6(3) . . ? C15 C14A C16 45.6(4) . . ? C13A C14A C16 44.4(3) . . ? N2 C14A C16 91.4(3) . . ? C14 C14A C16 91.0(4) . . ? O1 C1 O2 120.4(3) . . ? O1 C1 C2 119.0(3) . . ? O2 C1 C2 120.6(3) . . ? O1 C1 Ni1 58.37(19) . 1_455 ? O2 C1 Ni1 62.02(18) . 1_455 ? C2 C1 Ni1 177.3(3) . 1_455 ? C8 C2 C3 120.6(3) . . ? C8 C2 C1 119.6(3) . . ? C3 C2 C1 119.8(4) . . ? C4 C3 C2 119.5(4) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C6 119.6(4) . . ? C3 C4 C5 119.2(4) . . ? C6 C4 C5 121.2(3) . . ? O4 C5 O5 124.8(4) . . ? O4 C5 C4 117.6(3) . . ? O5 C5 C4 117.6(4) . . ? C7 C6 C4 120.3(4) . . ? C7 C6 H6 119.9 . . ? C4 C6 H6 119.9 . . ? O3 C7 C6 117.7(4) . . ? O3 C7 C8 122.3(4) . . ? C6 C7 C8 120.0(4) . . ? C2 C8 C7 120.0(4) . . ? C2 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? N1 C9 C10 122.8(4) . . ? N1 C9 H9 118.6 . . ? C10 C9 H9 118.6 . . ? C11 C10 C9 120.3(4) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C17 116.7(4) . . ? C10 C11 C12 122.5(4) . . ? C17 C11 C12 120.8(4) . . ? C12 C13 C14 119.6(6) . . ? C12 C13 C16A 60.3(4) . . ? C14 C13 C16A 88.0(6) . . ? C12 C13 C13A 49.1(3) . . ? C14 C13 C13A 88.9(5) . . ? C16A C13 C13A 93.9(4) . . ? C12 C13 C15A 90.2(5) . . ? C14 C13 C15A 44.3(5) . . ? C16A C13 C15A 43.7(3) . . ? C13A C13 C15A 92.6(3) . . ? N2 C14 C13 125.0(7) . . ? N2 C14 C15A 61.7(4) . . ? C13 C14 C15A 92.4(7) . . ? N2 C14 C14A 49.8(3) . . ? C13 C14 C14A 91.4(6) . . ? C15A C14 C14A 96.0(4) . . ? N2 C14 C16A 92.9(5) . . ? C13 C14 C16A 47.3(5) . . ? C15A C14 C16A 45.1(3) . . ? C14A C14 C16A 94.8(4) . . ? C14A C15 N2 61.2(4) . . ? C14A C15 C16 90.6(5) . . ? N2 C15 C16 121.7(6) . . ? C14A C15 C13A 45.8(3) . . ? N2 C15 C13A 91.5(5) . . ? C16 C15 C13A 44.8(4) . . ? C14A C15 C15A 90.6(4) . . ? N2 C15 C15A 44.6(3) . . ? C16 C15 C15A 91.3(5) . . ? C13A C15 C15A 90.4(3) . . ? C13A C16 C15 89.3(5) . . ? C13A C16 C12 60.1(4) . . ? C15 C16 C12 118.0(6) . . ? C13A C16 C14A 45.5(3) . . ? C15 C16 C14A 43.8(4) . . ? C12 C16 C14A 90.1(5) . . ? C13A C16 C16A 88.8(4) . . ? C15 C16 C16A 88.6(5) . . ? C12 C16 C16A 43.7(3) . . ? C14A C16 C16A 89.1(3) . . ? C11 C17 C18 120.0(4) . . ? C11 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? N1 C18 C17 122.8(4) . . ? N1 C18 H18 118.6 . . ? C17 C18 H18 118.6 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O4 0.88 1.87 2.617(4) 141.1 . O3 H3A O2W 0.82 1.90 2.713(5) 171.0 . O1W H1WB O2 0.88 1.93 2.744(4) 153.4 2_765 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.136 _refine_diff_density_min -0.712 _refine_diff_density_rms 0.112 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 -0.011 0.500 229 45 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 934993' ####################################################################### # # 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_upc3 #TrackingRef 'upc1-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H17 N6 O5 Zn' _chemical_formula_weight 522.80 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 9.6938(14) _cell_length_b 13.682(2) _cell_length_c 16.569(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.601(2) _cell_angle_gamma 90.00 _cell_volume 2193.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 2456 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 24.02 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1068 _exptl_absorpt_coefficient_mu 1.170 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8533 _exptl_absorpt_correction_T_max 0.8821 _exptl_absorpt_process_details 'APEX2 Software Suite (Bruker,2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 APEX2 CCD diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10718 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0478 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3860 _reflns_number_gt 3003 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 Software Suite (Bruker,2005)' _computing_cell_refinement 'APEX2 Software Suite' _computing_data_reduction 'APEX2 Software Suite' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2008)' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0456P)^2^+1.0768P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3860 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0962 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.9216(3) 0.0685(2) 0.41211(19) 0.0306(8) Uani 1 1 d . . . H1 H 1.8274 0.0550 0.4088 0.037 Uiso 1 1 calc R . . C2 C 2.1399(4) 0.0567(3) 0.4029(2) 0.0450(10) Uani 1 1 d . . . H2 H 2.2256 0.0314 0.3915 0.054 Uiso 1 1 calc R . . C3 C 2.1201(4) 0.1457(3) 0.4358(3) 0.0481(10) Uani 1 1 d . . . C4 C 1.9053(3) 0.2345(2) 0.47316(19) 0.0275(7) Uani 1 1 d . . . C5 C 1.9764(3) 0.2987(2) 0.52506(19) 0.0276(7) Uani 1 1 d . . . H5 H 2.0701 0.2902 0.5389 0.033 Uiso 1 1 calc R . . C6 C 1.9036(3) 0.3762(2) 0.55597(18) 0.0250(7) Uani 1 1 d . . . C7 C 1.7641(3) 0.3896(2) 0.53681(18) 0.0280(7) Uani 1 1 d . . . H7 H 1.7167 0.4417 0.5581 0.034 Uiso 1 1 calc R . . C8 C 1.6972(3) 0.3236(2) 0.48526(19) 0.0285(7) Uani 1 1 d . . . C9 C 1.7664(3) 0.2463(2) 0.4523(2) 0.0314(8) Uani 1 1 d . . . H9 H 1.7201 0.2031 0.4168 0.038 Uiso 1 1 calc R . . C10 C 1.4558(4) 0.3654(3) 0.5153(2) 0.0416(9) Uani 1 1 d . . . H10 H 1.4758 0.3802 0.5696 0.050 Uiso 1 1 calc R . . C11 C 1.3510(4) 0.3417(3) 0.4008(2) 0.0462(10) Uani 1 1 d . . . H11 H 1.2816 0.3374 0.3596 0.055 Uiso 1 1 calc R . . C12 C 1.4853(4) 0.3218(3) 0.3926(2) 0.0494(11) Uani 1 1 d . . . H12 H 1.5249 0.3011 0.3459 0.059 Uiso 1 1 calc R . . C13 C 1.9190(3) 0.4940(2) 0.66943(19) 0.0297(8) Uani 1 1 d . . . H13 H 1.8266 0.4902 0.6811 0.036 Uiso 1 1 calc R . . C14 C 2.1130(3) 0.4677(3) 0.6118(2) 0.0346(8) Uani 1 1 d . . . H14 H 2.1787 0.4441 0.5781 0.042 Uiso 1 1 calc R . . C15 C 2.1343(3) 0.5317(3) 0.6728(2) 0.0354(8) Uani 1 1 d . . . H15 H 2.2188 0.5604 0.6882 0.042 Uiso 1 1 calc R . . C16 C 1.7130(3) 0.6571(2) 0.82241(18) 0.0239(7) Uani 1 1 d . . . C17 C 1.5994(3) 0.7304(2) 0.80633(18) 0.0229(7) Uani 1 1 d . . . C18 C 1.6284(3) 0.8209(2) 0.77311(19) 0.0263(7) Uani 1 1 d . . . H18 H 1.7195 0.8390 0.7669 0.032 Uiso 1 1 calc R . . C19 C 1.5217(3) 0.8841(2) 0.7492(2) 0.0292(7) Uani 1 1 d . . . C20 C 1.3865(3) 0.8566(2) 0.75737(19) 0.0258(7) Uani 1 1 d . . . H20 H 1.3149 0.8979 0.7392 0.031 Uiso 1 1 calc R . . C21 C 1.3562(3) 0.7678(2) 0.79250(18) 0.0225(7) Uani 1 1 d . . . C22 C 1.2066(3) 0.7376(2) 0.79579(19) 0.0256(7) Uani 1 1 d . . . C23 C 1.4623(3) 0.7049(2) 0.81764(18) 0.0237(7) Uani 1 1 d . . . H23 H 1.4424 0.6457 0.8420 0.028 Uiso 1 1 calc R . . N1 N 2.0156(3) 0.00849(19) 0.38874(16) 0.0292(6) Uani 1 1 d . . . N2 N 1.9775(3) 0.15303(19) 0.44183(16) 0.0293(6) Uani 1 1 d . . . N3 N 1.3312(3) 0.3693(2) 0.47904(19) 0.0462(8) Uani 1 1 d . . . N4 N 1.5500(3) 0.3375(2) 0.46436(16) 0.0312(7) Uani 1 1 d . . . N5 N 1.9753(3) 0.44380(19) 0.60903(15) 0.0259(6) Uani 1 1 d . . . N6 N 2.0113(3) 0.54885(19) 0.70932(15) 0.0286(6) Uani 1 1 d . . . O1 O 1.6867(2) 0.56921(17) 0.82518(16) 0.0457(7) Uani 1 1 d . . . O2 O 1.8359(2) 0.69217(16) 0.82966(14) 0.0316(5) Uani 1 1 d . . . O3 O 1.1846(2) 0.66311(16) 0.84040(13) 0.0297(5) Uani 1 1 d . . . O4 O 1.1169(2) 0.78232(19) 0.75623(15) 0.0441(6) Uani 1 1 d . . . O5 O 1.5556(2) 0.97141(17) 0.71612(17) 0.0486(7) Uani 1 1 d . . . H5A H 1.4849 1.0020 0.7033 0.073 Uiso 1 1 calc R . . Zn1 Zn 1.99801(3) 0.61280(2) 0.81855(2) 0.02146(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0262(18) 0.0288(18) 0.037(2) -0.0080(16) -0.0004(14) 0.0004(15) C2 0.028(2) 0.037(2) 0.072(3) -0.018(2) 0.0113(18) -0.0001(17) C3 0.030(2) 0.041(2) 0.074(3) -0.019(2) 0.0099(19) -0.0014(17) C4 0.0297(18) 0.0249(17) 0.0282(18) -0.0038(14) 0.0036(14) 0.0000(14) C5 0.0296(18) 0.0233(17) 0.0298(19) 0.0004(14) 0.0012(14) 0.0031(14) C6 0.0323(18) 0.0208(17) 0.0221(16) -0.0007(13) 0.0030(13) -0.0009(14) C7 0.0314(18) 0.0262(17) 0.0271(17) -0.0044(14) 0.0061(14) 0.0038(15) C8 0.0245(17) 0.0328(19) 0.0283(18) -0.0001(15) 0.0010(14) 0.0042(15) C9 0.0298(18) 0.0298(19) 0.0343(19) -0.0095(15) -0.0013(15) 0.0011(15) C10 0.036(2) 0.051(2) 0.038(2) -0.0035(18) 0.0018(17) 0.0082(18) C11 0.036(2) 0.056(3) 0.045(2) -0.007(2) -0.0065(18) 0.0098(19) C12 0.038(2) 0.070(3) 0.040(2) -0.012(2) 0.0030(18) 0.013(2) C13 0.0272(18) 0.0294(18) 0.0328(19) -0.0082(15) 0.0052(15) -0.0030(15) C14 0.0300(19) 0.037(2) 0.037(2) -0.0110(16) 0.0062(15) -0.0018(16) C15 0.0252(18) 0.037(2) 0.044(2) -0.0118(17) 0.0056(16) -0.0048(15) C16 0.0209(17) 0.0233(17) 0.0273(18) -0.0044(14) 0.0013(13) -0.0009(14) C17 0.0210(16) 0.0201(16) 0.0275(17) -0.0029(13) 0.0022(13) 0.0003(13) C18 0.0165(15) 0.0270(18) 0.0357(19) -0.0031(14) 0.0045(14) -0.0033(14) C19 0.0280(18) 0.0194(16) 0.040(2) 0.0045(15) 0.0044(15) -0.0011(14) C20 0.0202(16) 0.0227(17) 0.0348(19) -0.0012(14) 0.0028(14) 0.0035(13) C21 0.0187(15) 0.0223(16) 0.0268(17) -0.0057(13) 0.0040(13) -0.0003(13) C22 0.0215(17) 0.0241(18) 0.0316(18) -0.0097(15) 0.0044(14) -0.0022(14) C23 0.0250(17) 0.0177(16) 0.0290(18) -0.0019(13) 0.0062(14) -0.0018(13) N1 0.0258(15) 0.0259(15) 0.0360(16) -0.0068(12) 0.0016(12) 0.0023(12) N2 0.0253(14) 0.0250(15) 0.0379(17) -0.0066(13) 0.0030(12) 0.0020(12) N3 0.0323(18) 0.055(2) 0.051(2) -0.0055(16) 0.0041(15) 0.0090(15) N4 0.0346(16) 0.0310(16) 0.0288(16) -0.0093(13) 0.0075(13) 0.0039(13) N5 0.0293(15) 0.0232(14) 0.0254(14) -0.0043(12) 0.0023(11) -0.0022(12) N6 0.0300(15) 0.0276(15) 0.0286(15) -0.0032(12) 0.0053(12) -0.0034(12) O1 0.0267(13) 0.0197(13) 0.089(2) 0.0013(13) -0.0107(13) 0.0005(11) O2 0.0169(11) 0.0269(12) 0.0513(15) -0.0033(11) 0.0031(10) -0.0001(10) O3 0.0223(12) 0.0269(13) 0.0402(14) -0.0007(11) 0.0040(10) -0.0068(10) O4 0.0216(12) 0.0460(16) 0.0636(18) 0.0101(13) -0.0058(12) 0.0006(12) O5 0.0289(13) 0.0267(14) 0.091(2) 0.0246(14) 0.0064(13) -0.0003(11) Zn1 0.0178(2) 0.0198(2) 0.0269(2) -0.00074(16) 0.00174(14) -0.00071(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.303(4) . ? C1 N2 1.356(4) . ? C1 H1 0.9300 . ? C2 C3 1.353(5) . ? C2 N1 1.381(4) . ? C2 H2 0.9300 . ? C3 N2 1.395(4) . ? C4 C9 1.378(4) . ? C4 C5 1.383(4) . ? C4 N2 1.431(4) . ? C5 C6 1.389(4) . ? C5 H5 0.9300 . ? C6 C7 1.381(4) . ? C6 N5 1.427(4) . ? C7 C8 1.377(4) . ? C7 H7 0.9300 . ? C8 C9 1.383(4) . ? C8 N4 1.459(4) . ? C9 H9 0.9300 . ? C10 N3 1.315(5) . ? C10 N4 1.337(4) . ? C10 H10 0.9300 . ? C11 C12 1.345(5) . ? C11 N3 1.375(5) . ? C11 H11 0.9300 . ? C12 N4 1.326(4) . ? C12 H12 0.9300 . ? C13 N6 1.314(4) . ? C13 N5 1.357(4) . ? C13 H13 0.9300 . ? C14 C15 1.343(5) . ? C14 N5 1.372(4) . ? C14 H14 0.9300 . ? C15 N6 1.390(4) . ? C15 H15 0.9300 . ? C16 O1 1.231(4) . ? C16 O2 1.283(3) . ? C16 C17 1.501(4) . ? C17 C18 1.391(4) . ? C17 C23 1.398(4) . ? C18 C19 1.386(4) . ? C18 H18 0.9300 . ? C19 O5 1.363(4) . ? C19 C20 1.379(4) . ? C20 C21 1.386(4) . ? C20 H20 0.9300 . ? C21 C23 1.385(4) . ? C21 C22 1.512(4) . ? C22 O4 1.220(4) . ? C22 O3 1.285(4) . ? C23 H23 0.9300 . ? N1 Zn1 2.027(3) 4_565 ? N6 Zn1 2.022(3) . ? O2 Zn1 1.929(2) . ? O3 Zn1 1.948(2) 1_455 ? O5 H5A 0.8200 . ? Zn1 O3 1.948(2) 1_655 ? Zn1 N1 2.027(3) 4_566 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 112.0(3) . . ? N1 C1 H1 124.0 . . ? N2 C1 H1 124.0 . . ? C3 C2 N1 110.7(3) . . ? C3 C2 H2 124.6 . . ? N1 C2 H2 124.6 . . ? C2 C3 N2 105.0(3) . . ? C9 C4 C5 121.5(3) . . ? C9 C4 N2 119.6(3) . . ? C5 C4 N2 119.0(3) . . ? C4 C5 C6 118.0(3) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C7 C6 C5 121.9(3) . . ? C7 C6 N5 119.2(3) . . ? C5 C6 N5 118.9(3) . . ? C8 C7 C6 118.1(3) . . ? C8 C7 H7 120.9 . . ? C6 C7 H7 120.9 . . ? C7 C8 C9 121.7(3) . . ? C7 C8 N4 118.5(3) . . ? C9 C8 N4 119.9(3) . . ? C4 C9 C8 118.8(3) . . ? C4 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? N3 C10 N4 111.5(3) . . ? N3 C10 H10 124.2 . . ? N4 C10 H10 124.2 . . ? C12 C11 N3 110.1(3) . . ? C12 C11 H11 125.0 . . ? N3 C11 H11 125.0 . . ? N4 C12 C11 106.5(3) . . ? N4 C12 H12 126.8 . . ? C11 C12 H12 126.8 . . ? N6 C13 N5 111.5(3) . . ? N6 C13 H13 124.2 . . ? N5 C13 H13 124.2 . . ? C15 C14 N5 106.5(3) . . ? C15 C14 H14 126.8 . . ? N5 C14 H14 126.8 . . ? C14 C15 N6 110.0(3) . . ? C14 C15 H15 125.0 . . ? N6 C15 H15 125.0 . . ? O1 C16 O2 123.7(3) . . ? O1 C16 C17 120.5(3) . . ? O2 C16 C17 115.7(3) . . ? C18 C17 C23 119.5(3) . . ? C18 C17 C16 120.0(3) . . ? C23 C17 C16 120.2(3) . . ? C19 C18 C17 120.2(3) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? O5 C19 C20 122.3(3) . . ? O5 C19 C18 117.9(3) . . ? C20 C19 C18 119.9(3) . . ? C19 C20 C21 120.5(3) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C23 C21 C20 119.9(3) . . ? C23 C21 C22 121.0(3) . . ? C20 C21 C22 118.9(3) . . ? O4 C22 O3 124.6(3) . . ? O4 C22 C21 119.8(3) . . ? O3 C22 C21 115.6(3) . . ? C21 C23 C17 119.9(3) . . ? C21 C23 H23 120.1 . . ? C17 C23 H23 120.1 . . ? C1 N1 C2 105.5(3) . . ? C1 N1 Zn1 130.6(2) . 4_565 ? C2 N1 Zn1 122.0(2) . 4_565 ? C1 N2 C3 106.7(3) . . ? C1 N2 C4 127.0(3) . . ? C3 N2 C4 126.2(3) . . ? C10 N3 C11 104.0(3) . . ? C12 N4 C10 108.0(3) . . ? C12 N4 C8 126.3(3) . . ? C10 N4 C8 125.7(3) . . ? C13 N5 C14 106.9(3) . . ? C13 N5 C6 125.4(3) . . ? C14 N5 C6 127.6(3) . . ? C13 N6 C15 105.1(3) . . ? C13 N6 Zn1 128.1(2) . . ? C15 N6 Zn1 124.6(2) . . ? C16 O2 Zn1 122.6(2) . . ? C22 O3 Zn1 111.1(2) . 1_455 ? C19 O5 H5A 109.5 . . ? O2 Zn1 O3 122.41(9) . 1_655 ? O2 Zn1 N6 115.30(10) . . ? O3 Zn1 N6 102.04(10) 1_655 . ? O2 Zn1 N1 116.47(10) . 4_566 ? O3 Zn1 N1 98.00(10) 1_655 4_566 ? N6 Zn1 N1 98.71(11) . 4_566 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.547 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.071 _database_code_depnum_ccdc_archive 'CCDC 934994' ####################################################################### # # 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_upc4 #TrackingRef 'upc1-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H6 N0 O11 Zn2' _chemical_formula_weight 504.95 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 16.784(2) _cell_length_b 12.9256(18) _cell_length_c 14.555(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.565(2) _cell_angle_gamma 90.00 _cell_volume 2993.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8299 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 27.51 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.120 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 1.639 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8030 _exptl_absorpt_correction_T_max 0.8403 _exptl_absorpt_process_details 'APEX2 Software Suite (Bruker,2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX2 CCD diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14402 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5251 _reflns_number_gt 4516 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 Software Suite (Bruker,2005)' _computing_cell_refinement 'APEX2 Software Suite' _computing_data_reduction 'APEX2 Software Suite' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2008)' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.1477P)^2^+16.9975P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5251 _refine_ls_number_parameters 262 _refine_ls_number_restraints 42 _refine_ls_R_factor_all 0.0768 _refine_ls_R_factor_gt 0.0695 _refine_ls_wR_factor_ref 0.2315 _refine_ls_wR_factor_gt 0.2229 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.105 _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 0.18210(4) 0.48622(5) 0.18028(5) 0.0189(3) Uani 1 1 d . . . Zn2 Zn -0.34551(4) 0.55293(5) -0.09925(5) 0.0202(3) Uani 1 1 d . . . O1 O 0.3840(3) 0.5422(5) 0.2110(5) 0.0499(13) Uani 1 1 d U . . O2 O 0.2682(3) 0.5859(4) 0.2447(4) 0.0399(11) Uani 1 1 d U . . O3 O 0.5881(3) 0.8229(4) 0.3584(4) 0.0329(11) Uani 1 1 d . . . O4 O 0.3778(3) 0.9882(4) 0.4959(4) 0.0429(14) Uani 1 1 d U . . O5 O 0.2743(4) 0.8761(6) 0.4678(6) 0.077(2) Uani 1 1 d U . . O6 O 0.0764(3) 0.5580(4) 0.1171(4) 0.0342(11) Uani 1 1 d U . . O7 O 0.0885(4) 0.6536(6) 0.2458(5) 0.072(2) Uani 1 1 d U . . O8 O -0.1450(3) 0.8823(4) 0.2470(4) 0.0466(14) Uani 1 1 d U . . O9 O -0.2712(4) 0.8595(6) 0.1458(5) 0.0652(19) Uani 1 1 d U . . O10 O -0.2275(2) 0.5848(3) -0.0858(3) 0.0238(9) Uani 1 1 d . . . C1 C 0.3429(4) 0.5995(5) 0.2494(5) 0.0264(14) Uani 1 1 d . . . C2 C 0.3865(4) 0.6908(5) 0.3059(5) 0.0288(14) Uani 1 1 d . . . C3 C 0.4695(4) 0.7140(5) 0.3114(5) 0.0305(15) Uani 1 1 d . . . H3 H 0.4985 0.6692 0.2833 0.037 Uiso 1 1 calc R . . C4 C 0.5095(4) 0.8032(5) 0.3583(5) 0.0274(14) Uani 1 1 d . . . C5 C 0.4653(4) 0.8660(5) 0.4034(5) 0.0282(14) Uani 1 1 d . . . H5 H 0.4909 0.9254 0.4356 0.034 Uiso 1 1 calc R . . C6 C 0.3846(4) 0.8426(6) 0.4017(5) 0.0332(16) Uani 1 1 d . . . C7 C 0.3407(4) 0.9057(6) 0.4587(6) 0.0404(19) Uani 1 1 d . . . C8 C 0.3439(4) 0.7543(6) 0.3529(6) 0.0373(18) Uani 1 1 d . . . H8 H 0.2896 0.7381 0.3518 0.045 Uiso 1 1 calc R . . C9 C 0.0474(4) 0.6218(6) 0.1643(5) 0.0383(18) Uani 1 1 d . . . C10 C -0.0423(4) 0.6557(6) 0.1175(5) 0.0330(16) Uani 1 1 d . . . C11 C -0.0764(4) 0.7306(6) 0.1637(5) 0.0358(17) Uani 1 1 d . . . H11 H -0.0428 0.7625 0.2199 0.043 Uiso 1 1 calc R . . C12 C -0.1605(4) 0.7568(6) 0.1251(5) 0.0306(15) Uani 1 1 d . . . C13 C -0.1966(4) 0.8377(6) 0.1756(6) 0.0346(16) Uani 1 1 d . . . C14 C -0.2112(4) 0.7089(5) 0.0412(5) 0.0277(14) Uani 1 1 d . . . H14 H -0.2676 0.7272 0.0157 0.033 Uiso 1 1 calc R . . C15 C -0.1777(4) 0.6337(5) -0.0047(5) 0.0231(13) Uani 1 1 d . . . C16 C -0.0924(4) 0.6086(5) 0.0343(5) 0.0266(14) Uani 1 1 d . . . H16 H -0.0692 0.5595 0.0036 0.032 Uiso 1 1 calc R . . O1W O 0.4118(6) 0.2925(8) 0.3316(7) 0.100(2) Uani 1 1 d U . . 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 0.0141(4) 0.0208(4) 0.0233(4) -0.0003(3) 0.0080(3) -0.0028(2) Zn2 0.0152(4) 0.0195(4) 0.0278(4) 0.0004(3) 0.0096(3) 0.0016(2) O1 0.032(2) 0.056(3) 0.065(3) -0.031(2) 0.021(2) -0.008(2) O2 0.025(2) 0.046(2) 0.052(2) -0.024(2) 0.0168(19) -0.0108(19) O3 0.021(2) 0.033(3) 0.050(3) -0.016(2) 0.018(2) -0.0112(19) O4 0.037(3) 0.042(3) 0.061(3) -0.032(3) 0.031(3) -0.020(2) O5 0.052(4) 0.079(4) 0.120(5) -0.059(4) 0.055(4) -0.031(3) O6 0.024(2) 0.042(3) 0.035(2) -0.012(2) 0.0075(19) 0.0094(19) O7 0.042(3) 0.102(4) 0.058(3) -0.042(3) -0.006(3) 0.023(3) O8 0.035(3) 0.053(3) 0.051(3) -0.028(3) 0.013(2) 0.007(2) O9 0.029(3) 0.075(4) 0.088(4) -0.042(4) 0.014(3) 0.009(3) O10 0.016(2) 0.029(2) 0.028(2) -0.0074(19) 0.0089(17) -0.0011(17) C1 0.019(3) 0.027(3) 0.033(3) -0.005(3) 0.008(3) -0.004(3) C2 0.021(3) 0.026(3) 0.041(4) -0.010(3) 0.013(3) -0.006(3) C3 0.025(3) 0.030(4) 0.041(4) -0.013(3) 0.017(3) -0.009(3) C4 0.020(3) 0.028(3) 0.036(4) -0.006(3) 0.012(3) -0.004(3) C5 0.025(3) 0.026(3) 0.036(4) -0.013(3) 0.012(3) -0.008(3) C6 0.029(3) 0.033(4) 0.042(4) -0.019(3) 0.017(3) -0.008(3) C7 0.028(4) 0.042(4) 0.061(5) -0.023(4) 0.028(4) -0.011(3) C8 0.025(3) 0.038(4) 0.055(5) -0.020(4) 0.022(3) -0.014(3) C9 0.025(3) 0.049(4) 0.038(4) -0.020(3) 0.005(3) 0.007(3) C10 0.023(3) 0.038(4) 0.038(4) -0.013(3) 0.008(3) 0.005(3) C11 0.022(3) 0.043(4) 0.038(4) -0.021(3) 0.004(3) 0.008(3) C12 0.022(3) 0.037(4) 0.036(4) -0.014(3) 0.013(3) 0.001(3) C13 0.030(4) 0.035(4) 0.043(4) -0.010(3) 0.017(3) 0.006(3) C14 0.017(3) 0.033(4) 0.035(4) -0.007(3) 0.011(3) 0.003(3) C15 0.019(3) 0.024(3) 0.028(3) -0.006(3) 0.011(2) -0.002(2) C16 0.021(3) 0.028(3) 0.032(3) -0.009(3) 0.010(3) 0.001(3) O1W 0.079(4) 0.117(5) 0.101(5) -0.008(4) 0.025(4) 0.003(4) _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 O8 1.931(5) 2_545 ? Zn1 O2 1.941(5) . ? Zn1 O6 1.953(5) . ? Zn1 O10 1.995(4) 3_565 ? Zn2 O3 1.940(4) 4_475 ? Zn2 O4 1.942(5) 2_545 ? Zn2 O10 1.971(4) . ? Zn2 O1 1.977(5) 3_565 ? O1 C1 1.258(8) . ? O1 Zn2 1.977(5) 3_565 ? O2 C1 1.246(8) . ? O3 C4 1.342(8) . ? O3 Zn2 1.940(4) 4_676 ? O4 C7 1.266(9) . ? O4 Zn2 1.942(5) 2 ? O5 C7 1.225(9) . ? O6 C9 1.266(8) . ? O7 C9 1.237(9) . ? O8 C13 1.261(9) . ? O8 Zn1 1.931(5) 2 ? O9 C13 1.221(9) . ? O10 C15 1.365(7) . ? O10 Zn1 1.995(4) 3_565 ? C1 C2 1.490(9) . ? C2 C8 1.402(9) . ? C2 C3 1.402(9) . ? C3 C4 1.398(9) . ? C3 H3 0.9300 . ? C4 C5 1.398(9) . ? C5 C6 1.380(9) . ? C5 H5 0.9300 . ? C6 C8 1.401(9) . ? C6 C7 1.512(9) . ? C8 H8 0.9300 . ? C9 C10 1.506(9) . ? C10 C16 1.377(9) . ? C10 C11 1.400(9) . ? C11 C12 1.384(9) . ? C11 H11 0.9300 . ? C12 C14 1.391(9) . ? C12 C13 1.512(9) . ? C14 C15 1.396(9) . ? C14 H14 0.9300 . ? C15 C16 1.401(9) . ? C16 H16 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O8 Zn1 O2 121.1(2) 2_545 . ? O8 Zn1 O6 100.7(2) 2_545 . ? O2 Zn1 O6 109.7(2) . . ? O8 Zn1 O10 108.5(2) 2_545 3_565 ? O2 Zn1 O10 104.46(19) . 3_565 ? O6 Zn1 O10 112.52(19) . 3_565 ? O3 Zn2 O4 109.2(2) 4_475 2_545 ? O3 Zn2 O10 108.44(19) 4_475 . ? O4 Zn2 O10 122.2(2) 2_545 . ? O3 Zn2 O1 104.4(2) 4_475 3_565 ? O4 Zn2 O1 105.7(3) 2_545 3_565 ? O10 Zn2 O1 105.4(2) . 3_565 ? C1 O1 Zn2 130.5(5) . 3_565 ? C1 O2 Zn1 134.5(5) . . ? C4 O3 Zn2 128.5(4) . 4_676 ? C7 O4 Zn2 118.3(5) . 2 ? C9 O6 Zn1 120.2(5) . . ? C13 O8 Zn1 120.9(5) . 2 ? C15 O10 Zn2 120.1(4) . . ? C15 O10 Zn1 123.2(4) . 3_565 ? Zn2 O10 Zn1 115.3(2) . 3_565 ? O2 C1 O1 125.3(6) . . ? O2 C1 C2 116.8(6) . . ? O1 C1 C2 117.9(6) . . ? C8 C2 C3 119.9(6) . . ? C8 C2 C1 119.7(6) . . ? C3 C2 C1 120.4(6) . . ? C4 C3 C2 121.2(6) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? O3 C4 C5 123.9(6) . . ? O3 C4 C3 118.4(6) . . ? C5 C4 C3 117.7(6) . . ? C6 C5 C4 121.9(6) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 C6 C8 120.3(6) . . ? C5 C6 C7 121.1(6) . . ? C8 C6 C7 118.3(6) . . ? O5 C7 O4 123.8(7) . . ? O5 C7 C6 120.6(7) . . ? O4 C7 C6 115.6(6) . . ? C6 C8 C2 118.9(6) . . ? C6 C8 H8 120.6 . . ? C2 C8 H8 120.6 . . ? O7 C9 O6 122.9(7) . . ? O7 C9 C10 120.6(6) . . ? O6 C9 C10 116.5(6) . . ? C16 C10 C11 120.0(6) . . ? C16 C10 C9 120.7(6) . . ? C11 C10 C9 119.1(6) . . ? C12 C11 C10 119.6(6) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C14 120.5(6) . . ? C11 C12 C13 119.1(6) . . ? C14 C12 C13 120.4(6) . . ? O9 C13 O8 123.0(7) . . ? O9 C13 C12 120.8(7) . . ? O8 C13 C12 116.2(6) . . ? C12 C14 C15 120.2(6) . . ? C12 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? O10 C15 C14 120.6(5) . . ? O10 C15 C16 120.5(5) . . ? C14 C15 C16 118.9(6) . . ? C10 C16 C15 120.8(6) . . ? C10 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? 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 O8 Zn1 O2 C1 109.0(7) 2_545 . . . ? O6 Zn1 O2 C1 -134.5(7) . . . . ? O10 Zn1 O2 C1 -13.6(8) 3_565 . . . ? O8 Zn1 O6 C9 77.5(6) 2_545 . . . ? O2 Zn1 O6 C9 -51.3(6) . . . . ? O10 Zn1 O6 C9 -167.2(6) 3_565 . . . ? O3 Zn2 O10 C15 80.5(5) 4_475 . . . ? O4 Zn2 O10 C15 -47.7(5) 2_545 . . . ? O1 Zn2 O10 C15 -168.1(5) 3_565 . . . ? O3 Zn2 O10 Zn1 -112.9(3) 4_475 . . 3_565 ? O4 Zn2 O10 Zn1 118.9(3) 2_545 . . 3_565 ? O1 Zn2 O10 Zn1 -1.5(3) 3_565 . . 3_565 ? Zn1 O2 C1 O1 -2.7(12) . . . . ? Zn1 O2 C1 C2 177.8(5) . . . . ? Zn2 O1 C1 O2 23.7(12) 3_565 . . . ? Zn2 O1 C1 C2 -156.7(5) 3_565 . . . ? O2 C1 C2 C8 2.0(10) . . . . ? O1 C1 C2 C8 -177.6(7) . . . . ? O2 C1 C2 C3 -177.3(7) . . . . ? O1 C1 C2 C3 3.1(11) . . . . ? C8 C2 C3 C4 -3.8(11) . . . . ? C1 C2 C3 C4 175.5(7) . . . . ? Zn2 O3 C4 C5 -10.0(10) 4_676 . . . ? Zn2 O3 C4 C3 170.8(5) 4_676 . . . ? C2 C3 C4 O3 -177.9(7) . . . . ? C2 C3 C4 C5 2.9(11) . . . . ? O3 C4 C5 C6 -179.8(7) . . . . ? C3 C4 C5 C6 -0.6(11) . . . . ? C4 C5 C6 C8 -0.7(12) . . . . ? C4 C5 C6 C7 174.2(7) . . . . ? Zn2 O4 C7 O5 16.6(13) 2 . . . ? Zn2 O4 C7 C6 -162.5(6) 2 . . . ? C5 C6 C7 O5 -169.6(9) . . . . ? C8 C6 C7 O5 5.3(13) . . . . ? C5 C6 C7 O4 9.5(12) . . . . ? C8 C6 C7 O4 -175.6(8) . . . . ? C5 C6 C8 C2 -0.2(12) . . . . ? C7 C6 C8 C2 -175.2(7) . . . . ? C3 C2 C8 C6 2.4(12) . . . . ? C1 C2 C8 C6 -176.9(7) . . . . ? Zn1 O6 C9 O7 11.0(12) . . . . ? Zn1 O6 C9 C10 -167.0(5) . . . . ? O7 C9 C10 C16 -169.7(9) . . . . ? O6 C9 C10 C16 8.4(12) . . . . ? O7 C9 C10 C11 5.5(13) . . . . ? O6 C9 C10 C11 -176.4(8) . . . . ? C16 C10 C11 C12 0.0(12) . . . . ? C9 C10 C11 C12 -175.2(7) . . . . ? C10 C11 C12 C14 0.3(12) . . . . ? C10 C11 C12 C13 180.0(7) . . . . ? Zn1 O8 C13 O9 3.0(12) 2 . . . ? Zn1 O8 C13 C12 -179.3(5) 2 . . . ? C11 C12 C13 O9 -177.0(8) . . . . ? C14 C12 C13 O9 2.7(12) . . . . ? C11 C12 C13 O8 5.3(11) . . . . ? C14 C12 C13 O8 -175.1(7) . . . . ? C11 C12 C14 C15 0.2(11) . . . . ? C13 C12 C14 C15 -179.5(7) . . . . ? Zn2 O10 C15 C14 -35.5(8) . . . . ? Zn1 O10 C15 C14 159.0(5) 3_565 . . . ? Zn2 O10 C15 C16 144.0(5) . . . . ? Zn1 O10 C15 C16 -21.5(8) 3_565 . . . ? C12 C14 C15 O10 178.6(6) . . . . ? C12 C14 C15 C16 -0.9(10) . . . . ? C11 C10 C16 C15 -0.7(11) . . . . ? C9 C10 C16 C15 174.4(7) . . . . ? O10 C15 C16 C10 -178.4(6) . . . . ? C14 C15 C16 C10 1.2(10) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.692 _refine_diff_density_min -2.098 _refine_diff_density_rms 0.235 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.001 -0.015 -0.019 1490 357 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 934995'