# Electronic Supplementary Material (ESI) for Chemical Communications # 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_Compound1 # data_d178jj _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24 N2 O4 Zn' _chemical_formula_weight 517.86 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2881(15) _cell_length_b 11.0671(16) _cell_length_c 11.2031(16) _cell_angle_alpha 88.609(3) _cell_angle_beta 70.855(3) _cell_angle_gamma 79.324(3) _cell_volume 1183.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2644 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 25.24 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 1.076 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6489 _exptl_absorpt_correction_T_max 0.9382 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15217 _diffrn_reflns_av_R_equivalents 0.0596 _diffrn_reflns_av_sigmaI/netI 0.0729 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5435 _reflns_number_gt 4422 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0635P)^2^+0.3217P] 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 5435 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1278 _refine_ls_wR_factor_gt 0.1220 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.57187(3) 0.61433(3) 0.58818(3) 0.01148(12) Uani 1 1 d . . . O1 O 0.6883(2) 0.7479(2) 0.6406(2) 0.0195(5) Uani 1 1 d . . . O2 O 0.5185(2) 0.6775(2) 0.7823(2) 0.0190(5) Uani 1 1 d . . . O3 O 0.4164(2) 0.50854(19) 0.6392(2) 0.0185(5) Uani 1 1 d . . . O4 O 0.3065(2) 0.37055(19) 0.59596(19) 0.0155(5) Uani 1 1 d . . . N1 N 0.7135(3) 0.4550(2) 0.6127(2) 0.0143(5) Uani 1 1 d . . . C1 C 0.6732(3) 0.3704(3) 0.6979(3) 0.0193(7) Uani 1 1 d . . . H1 H 0.5800 0.3862 0.7553 0.023 Uiso 1 1 calc R . . C2 C 0.7592(3) 0.2626(3) 0.7064(3) 0.0188(7) Uani 1 1 d . . . H2 H 0.7248 0.2052 0.7677 0.023 Uiso 1 1 calc R . . C3 C 0.8964(3) 0.2374(3) 0.6255(3) 0.0177(7) Uani 1 1 d . . . C4 C 0.9402(3) 0.3267(3) 0.5392(3) 0.0180(7) Uani 1 1 d . . . H4 H 1.0339 0.3147 0.4830 0.022 Uiso 1 1 calc R . . C5 C 0.8475(3) 0.4310(3) 0.5361(3) 0.0151(6) Uani 1 1 d . . . H5 H 0.8795 0.4904 0.4763 0.018 Uiso 1 1 calc R . . N2 N 1.4128(3) -0.2400(2) 0.5636(2) 0.0153(5) Uani 1 1 d . . . C6 C 1.2793(3) -0.2248(3) 0.6403(3) 0.0155(6) Uani 1 1 d . . . H6 H 1.2526 -0.2871 0.6982 0.019 Uiso 1 1 calc R . . C7 C 1.1795(3) -0.1239(3) 0.6394(3) 0.0155(6) Uani 1 1 d . . . H7 H 1.0858 -0.1189 0.6942 0.019 Uiso 1 1 calc R . . C8 C 1.2150(3) -0.0289(3) 0.5584(3) 0.0161(6) Uani 1 1 d . . . C9 C 1.3530(3) -0.0470(3) 0.4758(3) 0.0166(6) Uani 1 1 d . . . H9 H 1.3820 0.0128 0.4155 0.020 Uiso 1 1 calc R . . C10 C 1.4468(3) -0.1511(3) 0.4818(3) 0.0157(6) Uani 1 1 d . . . H10 H 1.5403 -0.1606 0.4253 0.019 Uiso 1 1 calc R . . C11 C 0.9872(3) 0.1210(3) 0.6301(3) 0.0209(7) Uani 1 1 d . . . H11 H 0.9478 0.0631 0.6883 0.025 Uiso 1 1 calc R . . C12 C 1.1221(3) 0.0892(3) 0.5584(3) 0.0178(7) Uani 1 1 d . . . H12 H 1.1613 0.1487 0.5023 0.021 Uiso 1 1 calc R . . C13 C 0.6114(3) 0.7423(3) 0.7532(3) 0.0135(6) Uani 1 1 d . . . C14 C 0.6315(3) 0.8143(3) 0.8557(3) 0.0131(6) Uani 1 1 d . . . C15 C 0.5550(3) 0.8019(3) 0.9817(3) 0.0159(6) Uani 1 1 d . . . H15 H 0.4873 0.7501 1.0030 0.019 Uiso 1 1 calc R . . C16 C 0.5775(3) 0.8651(3) 1.0763(3) 0.0189(7) Uani 1 1 d . . . H16 H 0.5246 0.8564 1.1621 0.023 Uiso 1 1 calc R . . C17 C 0.6760(3) 0.9409(3) 1.0475(3) 0.0197(7) Uani 1 1 d . . . C18 C 0.7513(3) 0.9532(3) 0.9219(3) 0.0195(7) Uani 1 1 d . . . H18 H 0.8186 1.0054 0.9006 0.023 Uiso 1 1 calc R . . C19 C 0.7298(3) 0.8901(3) 0.8265(3) 0.0148(6) Uani 1 1 d . . . H19 H 0.7828 0.8989 0.7407 0.018 Uiso 1 1 calc R . . C20 C 0.7020(4) 1.0063(3) 1.1513(3) 0.0295(8) Uani 1 1 d . . . H20A H 0.7898 0.9644 1.1623 0.044 Uiso 1 1 calc R . . H20B H 0.6245 1.0055 1.2304 0.044 Uiso 1 1 calc R . . H20C H 0.7088 1.0916 1.1288 0.044 Uiso 1 1 calc R . . C21 C 0.3331(3) 0.4350(3) 0.6741(3) 0.0108(6) Uani 1 1 d . . . C22 C 0.2625(3) 0.4238(3) 0.8119(3) 0.0112(6) Uani 1 1 d . . . C23 C 0.1662(3) 0.3452(3) 0.8548(3) 0.0154(6) Uani 1 1 d . . . H23 H 0.1467 0.2973 0.7957 0.018 Uiso 1 1 calc R . . C24 C 0.0996(3) 0.3370(3) 0.9826(3) 0.0180(7) Uani 1 1 d . . . H24 H 0.0343 0.2834 1.0106 0.022 Uiso 1 1 calc R . . C25 C 0.1262(3) 0.4061(3) 1.0717(3) 0.0172(7) Uani 1 1 d . . . C26 C 0.2229(3) 0.4839(3) 1.0270(3) 0.0184(7) Uani 1 1 d . . . H26 H 0.2434 0.5313 1.0859 0.022 Uiso 1 1 calc R . . C27 C 0.2894(3) 0.4936(3) 0.8993(3) 0.0158(6) Uani 1 1 d . . . H27 H 0.3537 0.5480 0.8712 0.019 Uiso 1 1 calc R . . C28 C 0.0540(4) 0.3995(3) 1.2107(3) 0.0256(8) Uani 1 1 d . . . H28A H -0.0131 0.3439 1.2252 0.038 Uiso 1 1 calc R . . H28B H 0.0043 0.4818 1.2461 0.038 Uiso 1 1 calc R . . H28C H 0.1236 0.3685 1.2518 0.038 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 0.01190(19) 0.01186(19) 0.00987(19) 0.00068(13) -0.00172(13) -0.00368(13) O1 0.0213(12) 0.0238(12) 0.0126(11) 0.0002(9) -0.0036(9) -0.0059(10) O2 0.0206(12) 0.0191(11) 0.0185(12) -0.0007(9) -0.0052(9) -0.0092(9) O3 0.0174(11) 0.0217(12) 0.0156(11) 0.0031(9) -0.0004(9) -0.0112(9) O4 0.0166(11) 0.0197(11) 0.0097(10) -0.0012(9) -0.0025(8) -0.0051(9) N1 0.0125(12) 0.0190(13) 0.0110(12) 0.0003(10) -0.0014(10) -0.0068(10) C1 0.0135(15) 0.0286(18) 0.0158(16) 0.0046(13) -0.0035(13) -0.0069(13) C2 0.0161(16) 0.0234(17) 0.0163(16) 0.0092(13) -0.0037(13) -0.0066(13) C3 0.0150(15) 0.0214(16) 0.0167(16) 0.0039(13) -0.0062(13) -0.0025(13) C4 0.0139(15) 0.0265(17) 0.0118(15) 0.0040(13) -0.0013(12) -0.0054(13) C5 0.0165(15) 0.0187(16) 0.0101(15) 0.0023(12) -0.0021(12) -0.0080(12) N2 0.0159(13) 0.0141(13) 0.0161(13) 0.0016(10) -0.0048(11) -0.0045(10) C6 0.0167(15) 0.0137(15) 0.0158(16) 0.0031(12) -0.0037(12) -0.0054(12) C7 0.0127(14) 0.0198(16) 0.0158(15) 0.0017(12) -0.0051(12) -0.0068(12) C8 0.0135(15) 0.0204(16) 0.0147(15) 0.0023(12) -0.0049(12) -0.0038(12) C9 0.0169(15) 0.0159(15) 0.0156(16) 0.0053(12) -0.0028(12) -0.0048(12) C10 0.0139(15) 0.0181(16) 0.0134(15) 0.0007(12) -0.0024(12) -0.0030(12) C11 0.0195(16) 0.0187(17) 0.0208(17) 0.0049(13) -0.0011(13) -0.0051(13) C12 0.0209(16) 0.0170(16) 0.0162(16) 0.0029(12) -0.0064(13) -0.0053(13) C13 0.0134(14) 0.0118(14) 0.0145(15) -0.0012(12) -0.0051(12) 0.0005(11) C14 0.0131(14) 0.0119(14) 0.0136(15) 0.0011(12) -0.0049(12) -0.0001(11) C15 0.0108(14) 0.0187(16) 0.0152(15) 0.0006(12) -0.0014(12) -0.0011(12) C16 0.0164(16) 0.0240(17) 0.0118(15) -0.0027(13) -0.0032(12) 0.0053(13) C17 0.0196(16) 0.0169(16) 0.0229(17) -0.0057(13) -0.0109(14) 0.0042(13) C18 0.0231(17) 0.0152(16) 0.0239(18) 0.0024(13) -0.0107(14) -0.0073(13) C19 0.0192(15) 0.0145(15) 0.0097(15) 0.0031(12) -0.0029(12) -0.0045(12) C20 0.036(2) 0.031(2) 0.0253(19) -0.0059(16) -0.0173(17) -0.0014(16) C21 0.0064(13) 0.0104(14) 0.0119(15) 0.0030(11) -0.0006(11) 0.0025(11) C22 0.0084(13) 0.0133(14) 0.0100(14) 0.0018(11) -0.0023(11) 0.0012(11) C23 0.0157(15) 0.0136(15) 0.0160(16) 0.0008(12) -0.0046(12) -0.0014(12) C24 0.0123(15) 0.0205(16) 0.0172(16) 0.0057(13) -0.0003(12) -0.0025(12) C25 0.0104(14) 0.0226(17) 0.0116(15) 0.0038(12) 0.0011(12) 0.0050(12) C26 0.0191(16) 0.0252(17) 0.0105(15) -0.0031(13) -0.0057(13) -0.0011(13) C27 0.0133(15) 0.0176(16) 0.0161(16) 0.0005(12) -0.0041(12) -0.0036(12) C28 0.0198(17) 0.037(2) 0.0117(16) 0.0068(14) 0.0013(13) 0.0024(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 Zn1 O4 2.054(2) 2_666 ? Zn1 O3 2.078(2) . ? Zn1 N1 2.143(3) . ? Zn1 N2 2.157(3) 1_465 ? Zn1 O2 2.161(2) . ? Zn1 O1 2.264(2) . ? Zn1 C13 2.535(3) . ? O1 C13 1.258(4) . ? O2 C13 1.254(4) . ? O3 C21 1.254(3) . ? O4 C21 1.268(4) . ? O4 Zn1 2.054(2) 2_666 ? N1 C1 1.342(4) . ? N1 C5 1.345(4) . ? C1 C2 1.369(4) . ? C2 C3 1.386(4) . ? C3 C4 1.395(4) . ? C3 C11 1.455(4) . ? C4 C5 1.362(4) . ? N2 C6 1.341(4) . ? N2 C10 1.343(4) . ? N2 Zn1 2.157(3) 1_645 ? C6 C7 1.372(4) . ? C7 C8 1.393(4) . ? C8 C9 1.398(4) . ? C8 C12 1.470(4) . ? C9 C10 1.375(4) . ? C11 C12 1.341(5) . ? C13 C14 1.502(4) . ? C14 C19 1.384(4) . ? C14 C15 1.390(4) . ? C15 C16 1.387(4) . ? C16 C17 1.387(5) . ? C17 C18 1.383(5) . ? C17 C20 1.504(4) . ? C18 C19 1.389(4) . ? C21 C22 1.489(4) . ? C22 C27 1.387(4) . ? C22 C23 1.399(4) . ? C23 C24 1.379(4) . ? C24 C25 1.396(5) . ? C25 C26 1.398(4) . ? C25 C28 1.496(4) . ? C26 C27 1.379(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Zn1 O3 122.92(8) 2_666 . ? O4 Zn1 N1 92.43(9) 2_666 . ? O3 Zn1 N1 87.51(9) . . ? O4 Zn1 N2 89.66(9) 2_666 1_465 ? O3 Zn1 N2 85.92(9) . 1_465 ? N1 Zn1 N2 173.20(9) . 1_465 ? O4 Zn1 O2 145.90(8) 2_666 . ? O3 Zn1 O2 91.04(8) . . ? N1 Zn1 O2 92.05(9) . . ? N2 Zn1 O2 89.84(9) 1_465 . ? O4 Zn1 O1 86.62(8) 2_666 . ? O3 Zn1 O1 150.39(8) . . ? N1 Zn1 O1 93.77(9) . . ? N2 Zn1 O1 92.81(9) 1_465 . ? O2 Zn1 O1 59.36(8) . . ? O4 Zn1 C13 116.32(9) 2_666 . ? O3 Zn1 C13 120.68(9) . . ? N1 Zn1 C13 93.13(9) . . ? N2 Zn1 C13 91.74(9) 1_465 . ? O2 Zn1 C13 29.64(9) . . ? O1 Zn1 C13 29.72(8) . . ? C13 O1 Zn1 87.14(17) . . ? C13 O2 Zn1 91.94(18) . . ? C21 O3 Zn1 172.9(2) . . ? C21 O4 Zn1 113.24(18) . 2_666 ? C1 N1 C5 116.3(3) . . ? C1 N1 Zn1 122.9(2) . . ? C5 N1 Zn1 120.6(2) . . ? N1 C1 C2 123.5(3) . . ? C1 C2 C3 119.8(3) . . ? C2 C3 C4 116.9(3) . . ? C2 C3 C11 120.4(3) . . ? C4 C3 C11 122.7(3) . . ? C5 C4 C3 119.5(3) . . ? N1 C5 C4 123.9(3) . . ? C6 N2 C10 116.9(3) . . ? C6 N2 Zn1 121.6(2) . 1_645 ? C10 N2 Zn1 121.0(2) . 1_645 ? N2 C6 C7 123.3(3) . . ? C6 C7 C8 120.2(3) . . ? C7 C8 C9 116.2(3) . . ? C7 C8 C12 125.3(3) . . ? C9 C8 C12 118.4(3) . . ? C10 C9 C8 120.1(3) . . ? N2 C10 C9 123.2(3) . . ? C12 C11 C3 125.0(3) . . ? C11 C12 C8 126.1(3) . . ? O2 C13 O1 121.6(3) . . ? O2 C13 C14 119.1(3) . . ? O1 C13 C14 119.4(3) . . ? O2 C13 Zn1 58.43(15) . . ? O1 C13 Zn1 63.13(16) . . ? C14 C13 Zn1 177.3(2) . . ? C19 C14 C15 119.2(3) . . ? C19 C14 C13 120.6(3) . . ? C15 C14 C13 120.2(3) . . ? C16 C15 C14 120.0(3) . . ? C15 C16 C17 121.0(3) . . ? C18 C17 C16 118.6(3) . . ? C18 C17 C20 120.9(3) . . ? C16 C17 C20 120.5(3) . . ? C17 C18 C19 120.8(3) . . ? C14 C19 C18 120.4(3) . . ? O3 C21 O4 122.2(3) . . ? O3 C21 C22 118.7(3) . . ? O4 C21 C22 119.0(2) . . ? C27 C22 C23 119.2(3) . . ? C27 C22 C21 120.2(3) . . ? C23 C22 C21 120.6(3) . . ? C24 C23 C22 120.1(3) . . ? C23 C24 C25 121.3(3) . . ? C24 C25 C26 117.7(3) . . ? C24 C25 C28 122.1(3) . . ? C26 C25 C28 120.2(3) . . ? C27 C26 C25 121.5(3) . . ? C26 C27 C22 120.1(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.879 _refine_diff_density_min -0.697 _refine_diff_density_rms 0.101 _database_code_depnum_ccdc_archive 'CCDC 957292' ####################################################################### # # 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_compound2 # data_d046jj _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24 N2 O4 Zn' _chemical_formula_weight 517.86 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 15.6758(14) _cell_length_b 13.6884(12) _cell_length_c 22.957(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.617(2) _cell_angle_gamma 90.00 _cell_volume 4807.1(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2258 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 24.04 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2144 _exptl_absorpt_coefficient_mu 1.059 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6587 _exptl_absorpt_correction_T_max 0.9200 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16582 _diffrn_reflns_av_R_equivalents 0.0632 _diffrn_reflns_av_sigmaI/netI 0.0732 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5519 _reflns_number_gt 4360 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0643P)^2^+2.4280P] 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 5519 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0680 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1348 _refine_ls_wR_factor_gt 0.1200 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 0.59648(2) 0.40393(2) 0.205165(14) 0.00973(12) Uani 1 1 d . . . O1 O 0.60020(14) 0.39360(14) 0.11219(10) 0.0175(5) Uani 1 1 d . . . O2 O 0.72690(14) 0.39352(15) 0.17616(9) 0.0198(5) Uani 1 1 d . . . O3 O 0.46084(13) 0.40293(15) 0.18323(9) 0.0179(5) Uani 1 1 d . . . O4 O 0.33341(13) 0.41299(14) 0.20868(9) 0.0143(4) Uani 1 1 d . . . N1 N 0.59247(15) 0.24733(18) 0.21253(10) 0.0121(5) Uani 1 1 d . . . C1 C 0.52806(18) 0.1932(2) 0.17901(12) 0.0115(6) Uani 1 1 d . . . H1 H 0.4805 0.2258 0.1538 0.014 Uiso 1 1 calc R . . C2 C 0.52831(19) 0.0928(2) 0.17987(13) 0.0127(6) Uani 1 1 d . . . H2 H 0.4813 0.0578 0.1556 0.015 Uiso 1 1 calc R . . C3 C 0.59706(18) 0.0419(2) 0.21602(12) 0.0111(6) Uani 1 1 d . . . C4 C 0.6629(2) 0.0989(2) 0.25142(13) 0.0144(6) Uani 1 1 d . . . H4 H 0.7108 0.0683 0.2776 0.017 Uiso 1 1 calc R . . C5 C 0.65812(18) 0.1994(2) 0.24816(12) 0.0135(6) Uani 1 1 d . . . H5 H 0.7036 0.2365 0.2724 0.016 Uiso 1 1 calc R . . N2 N 0.58527(15) -0.43911(18) 0.19887(10) 0.0139(5) Uani 1 1 d . . . C6 C 0.62139(19) -0.3789(2) 0.24369(13) 0.0143(6) Uani 1 1 d . . . H6 H 0.6540 -0.4072 0.2795 0.017 Uiso 1 1 calc R . . C7 C 0.61404(19) -0.2791(2) 0.24087(13) 0.0159(6) Uani 1 1 d . . . H7 H 0.6411 -0.2401 0.2740 0.019 Uiso 1 1 calc R . . C8 C 0.56652(18) -0.2353(2) 0.18901(13) 0.0137(6) Uani 1 1 d . . . C9 C 0.5282(2) -0.2972(2) 0.14290(13) 0.0186(7) Uani 1 1 d . . . H9 H 0.4944 -0.2709 0.1069 0.022 Uiso 1 1 calc R . . C10 C 0.5389(2) -0.3971(2) 0.14914(13) 0.0180(7) Uani 1 1 d . . . H10 H 0.5123 -0.4379 0.1168 0.022 Uiso 1 1 calc R . . C11 C 0.60481(19) -0.0644(2) 0.21951(13) 0.0149(6) Uani 1 1 d . . . H12 H 0.6486 -0.0901 0.2511 0.018 Uiso 1 1 calc R . . C12 C 0.55654(19) -0.1295(2) 0.18286(13) 0.0150(6) Uani 1 1 d . . . H13 H 0.5129 -0.1052 0.1507 0.018 Uiso 1 1 calc R . . C13 C 0.6825(2) 0.38957(19) 0.12339(13) 0.0134(6) Uani 1 1 d . . . C14 C 0.72810(19) 0.3813(2) 0.07249(13) 0.0136(6) Uani 1 1 d . . . C15 C 0.8181(2) 0.3808(2) 0.08322(14) 0.0180(7) Uani 1 1 d . . . H3 H 0.8512 0.3843 0.1231 0.022 Uiso 1 1 calc R . . C16 C 0.8607(2) 0.3751(2) 0.03630(16) 0.0239(7) Uani 1 1 d . . . H16 H 0.9228 0.3749 0.0444 0.029 Uiso 1 1 calc R . . C17 C 0.8134(2) 0.3698(2) -0.02248(15) 0.0243(8) Uani 1 1 d . . . C18 C 0.7227(2) 0.3697(2) -0.03287(14) 0.0243(8) Uani 1 1 d . . . H18 H 0.6894 0.3654 -0.0727 0.029 Uiso 1 1 calc R . . C19 C 0.6800(2) 0.3757(2) 0.01392(13) 0.0170(6) Uani 1 1 d . . . H19 H 0.6179 0.3760 0.0060 0.020 Uiso 1 1 calc R . . C20 C 0.8605(3) 0.3641(3) -0.07261(17) 0.0389(10) Uani 1 1 d . . . H20A H 0.8977 0.4219 -0.0718 0.058 Uiso 1 1 calc R . . H20B H 0.8178 0.3615 -0.1108 0.058 Uiso 1 1 calc R . . H20C H 0.8969 0.3052 -0.0681 0.058 Uiso 1 1 calc R . . C21 C 0.37985(18) 0.40515(18) 0.17019(12) 0.0095(6) Uani 1 1 d . . . C22 C 0.33391(19) 0.39669(19) 0.10607(13) 0.0124(6) Uani 1 1 d . . . C23 C 0.3825(2) 0.3881(2) 0.06227(13) 0.0178(7) Uani 1 1 d . . . H23 H 0.4446 0.3896 0.0730 0.021 Uiso 1 1 calc R . . C24 C 0.3402(3) 0.3773(2) 0.00301(14) 0.0259(8) Uani 1 1 d . . . H24 H 0.3738 0.3717 -0.0266 0.031 Uiso 1 1 calc R . . C25 C 0.2499(3) 0.3745(2) -0.01406(14) 0.0272(8) Uani 1 1 d . . . C26 C 0.2021(2) 0.3824(2) 0.02985(16) 0.0289(9) Uani 1 1 d . . . H26 H 0.1401 0.3801 0.0190 0.035 Uiso 1 1 calc R . . C27 C 0.2434(2) 0.3936(2) 0.08969(15) 0.0205(7) Uani 1 1 d . . . H27 H 0.2096 0.3991 0.1192 0.025 Uiso 1 1 calc R . . C28 C 0.2048(3) 0.3628(3) -0.07908(16) 0.0458(12) Uani 1 1 d . . . H28A H 0.2404 0.3213 -0.0992 0.069 Uiso 1 1 calc R . . H28B H 0.1972 0.4271 -0.0983 0.069 Uiso 1 1 calc R . . H28C H 0.1474 0.3325 -0.0818 0.069 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 0.01070(18) 0.00774(18) 0.01030(18) -0.00049(12) 0.00134(12) -0.00033(12) O1 0.0168(11) 0.0157(11) 0.0213(11) 0.0013(9) 0.0071(9) 0.0012(8) O2 0.0244(12) 0.0228(12) 0.0127(10) -0.0036(9) 0.0050(9) -0.0059(9) O3 0.0091(10) 0.0228(12) 0.0190(11) 0.0004(9) -0.0032(8) 0.0006(8) O4 0.0165(11) 0.0152(11) 0.0111(10) 0.0009(8) 0.0027(8) 0.0019(8) N1 0.0148(12) 0.0095(12) 0.0130(12) -0.0005(9) 0.0051(10) -0.0014(9) C1 0.0119(14) 0.0119(14) 0.0106(13) 0.0002(11) 0.0022(11) 0.0016(11) C2 0.0120(14) 0.0144(15) 0.0119(13) -0.0003(11) 0.0027(11) -0.0017(11) C3 0.0134(14) 0.0103(14) 0.0104(13) -0.0005(10) 0.0043(11) 0.0013(11) C4 0.0144(14) 0.0147(15) 0.0136(14) -0.0009(11) 0.0018(11) 0.0033(12) C5 0.0108(14) 0.0136(15) 0.0150(14) -0.0009(11) 0.0004(11) -0.0021(11) N2 0.0125(13) 0.0110(12) 0.0171(12) -0.0010(10) 0.0010(10) -0.0010(10) C6 0.0119(14) 0.0135(15) 0.0160(14) 0.0008(11) 0.0001(12) -0.0004(11) C7 0.0167(15) 0.0133(15) 0.0167(14) -0.0038(12) 0.0016(12) -0.0049(12) C8 0.0078(13) 0.0120(15) 0.0198(14) -0.0028(12) -0.0006(11) -0.0038(11) C9 0.0224(17) 0.0114(15) 0.0187(15) 0.0017(12) -0.0027(13) 0.0013(12) C10 0.0247(17) 0.0109(15) 0.0154(14) 0.0000(11) -0.0019(13) -0.0011(12) C11 0.0145(15) 0.0126(14) 0.0168(14) 0.0023(12) 0.0022(12) 0.0014(11) C12 0.0137(15) 0.0131(15) 0.0178(15) 0.0021(12) 0.0023(12) -0.0009(12) C13 0.0208(16) 0.0044(13) 0.0160(14) -0.0013(10) 0.0063(12) -0.0030(11) C14 0.0189(16) 0.0085(14) 0.0137(14) 0.0003(11) 0.0044(12) -0.0002(11) C15 0.0201(16) 0.0142(15) 0.0197(15) 0.0027(12) 0.0045(13) 0.0018(12) C16 0.0253(18) 0.0180(16) 0.0330(19) 0.0068(14) 0.0168(15) 0.0060(14) C17 0.046(2) 0.0096(15) 0.0231(17) 0.0034(13) 0.0209(16) 0.0044(15) C18 0.049(2) 0.0112(15) 0.0127(15) 0.0026(12) 0.0070(15) 0.0000(15) C19 0.0224(16) 0.0105(14) 0.0165(15) 0.0000(11) 0.0008(12) 0.0004(12) C20 0.067(3) 0.027(2) 0.034(2) 0.0024(17) 0.037(2) 0.0023(19) C21 0.0121(14) 0.0034(12) 0.0108(13) 0.0018(10) -0.0021(11) -0.0007(10) C22 0.0170(15) 0.0046(13) 0.0125(13) 0.0004(10) -0.0032(11) 0.0001(11) C23 0.0242(17) 0.0126(15) 0.0143(14) 0.0022(11) -0.0005(12) 0.0007(12) C24 0.050(2) 0.0115(16) 0.0146(15) 0.0013(12) 0.0028(15) -0.0004(15) C25 0.048(2) 0.0067(14) 0.0165(16) 0.0023(12) -0.0147(15) -0.0015(15) C26 0.0252(18) 0.0137(16) 0.036(2) 0.0033(14) -0.0181(16) -0.0012(13) C27 0.0181(16) 0.0118(15) 0.0279(17) -0.0006(12) -0.0033(13) -0.0001(12) C28 0.078(3) 0.0171(19) 0.0256(19) -0.0013(15) -0.026(2) 0.001(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 O4 2.046(2) 2_655 ? Zn1 O3 2.075(2) . ? Zn1 N1 2.152(2) . ? Zn1 O1 2.153(2) . ? Zn1 N2 2.158(3) 1_565 ? Zn1 O2 2.289(2) . ? Zn1 C13 2.547(3) . ? O1 C13 1.260(4) . ? O2 C13 1.260(4) . ? O3 C21 1.240(3) . ? O4 C21 1.266(3) . ? O4 Zn1 2.046(2) 2_655 ? N1 C5 1.338(4) . ? N1 C1 1.350(3) . ? C1 C2 1.374(4) . ? C2 C3 1.395(4) . ? C3 C4 1.403(4) . ? C3 C11 1.462(4) . ? C4 C5 1.379(4) . ? N2 C10 1.341(4) . ? N2 C6 1.343(4) . ? N2 Zn1 2.158(3) 1_545 ? C6 C7 1.372(4) . ? C7 C8 1.395(4) . ? C8 C9 1.387(4) . ? C8 C12 1.460(4) . ? C9 C10 1.381(4) . ? C11 C12 1.340(4) . ? C13 C14 1.502(4) . ? C14 C15 1.378(4) . ? C14 C19 1.393(4) . ? C15 C16 1.388(4) . ? C16 C17 1.392(5) . ? C17 C18 1.390(5) . ? C17 C20 1.499(4) . ? C18 C19 1.386(4) . ? C21 C22 1.495(4) . ? C22 C27 1.387(4) . ? C22 C23 1.393(4) . ? C23 C24 1.385(4) . ? C24 C25 1.384(5) . ? C25 C26 1.385(6) . ? C25 C28 1.514(4) . ? C26 C27 1.393(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Zn1 O3 122.72(8) 2_655 . ? O4 Zn1 N1 90.18(8) 2_655 . ? O3 Zn1 N1 88.08(8) . . ? O4 Zn1 O1 146.87(9) 2_655 . ? O3 Zn1 O1 90.41(8) . . ? N1 Zn1 O1 91.14(8) . . ? O4 Zn1 N2 91.32(8) 2_655 1_565 ? O3 Zn1 N2 85.77(8) . 1_565 ? N1 Zn1 N2 173.49(9) . 1_565 ? O1 Zn1 N2 91.06(8) . 1_565 ? O4 Zn1 O2 87.69(8) 2_655 . ? O3 Zn1 O2 149.54(8) . . ? N1 Zn1 O2 90.23(8) . . ? O1 Zn1 O2 59.20(8) . . ? N2 Zn1 O2 96.16(8) 1_565 . ? O4 Zn1 C13 117.28(9) 2_655 . ? O3 Zn1 C13 119.99(9) . . ? N1 Zn1 C13 90.59(9) . . ? O1 Zn1 C13 29.62(9) . . ? N2 Zn1 C13 94.35(9) 1_565 . ? O2 Zn1 C13 29.59(8) . . ? C13 O1 Zn1 92.80(18) . . ? C13 O2 Zn1 86.62(18) . . ? C21 O3 Zn1 178.2(2) . . ? C21 O4 Zn1 113.59(18) . 2_655 ? C5 N1 C1 117.3(2) . . ? C5 N1 Zn1 120.30(19) . . ? C1 N1 Zn1 122.23(19) . . ? N1 C1 C2 122.8(3) . . ? C1 C2 C3 120.5(3) . . ? C2 C3 C4 116.2(3) . . ? C2 C3 C11 125.1(3) . . ? C4 C3 C11 118.7(3) . . ? C5 C4 C3 119.9(3) . . ? N1 C5 C4 123.2(3) . . ? C10 N2 C6 116.7(3) . . ? C10 N2 Zn1 120.29(19) . 1_545 ? C6 N2 Zn1 123.0(2) . 1_545 ? N2 C6 C7 123.9(3) . . ? C6 C7 C8 119.5(3) . . ? C9 C8 C7 116.8(3) . . ? C9 C8 C12 120.9(3) . . ? C7 C8 C12 122.4(3) . . ? C10 C9 C8 120.2(3) . . ? N2 C10 C9 122.9(3) . . ? C12 C11 C3 126.8(3) . . ? C11 C12 C8 124.4(3) . . ? O2 C13 O1 121.4(3) . . ? O2 C13 C14 119.6(3) . . ? O1 C13 C14 119.0(3) . . ? O2 C13 Zn1 63.79(16) . . ? O1 C13 Zn1 57.59(15) . . ? C14 C13 Zn1 176.6(2) . . ? C15 C14 C19 119.3(3) . . ? C15 C14 C13 120.3(3) . . ? C19 C14 C13 120.4(3) . . ? C14 C15 C16 120.6(3) . . ? C15 C16 C17 120.7(3) . . ? C18 C17 C16 118.4(3) . . ? C18 C17 C20 121.7(3) . . ? C16 C17 C20 119.9(3) . . ? C19 C18 C17 121.0(3) . . ? C18 C19 C14 120.0(3) . . ? O3 C21 O4 123.2(3) . . ? O3 C21 C22 118.9(3) . . ? O4 C21 C22 117.8(2) . . ? C27 C22 C23 119.4(3) . . ? C27 C22 C21 120.9(3) . . ? C23 C22 C21 119.7(3) . . ? C24 C23 C22 119.8(3) . . ? C25 C24 C23 121.5(3) . . ? C24 C25 C26 118.3(3) . . ? C24 C25 C28 120.7(4) . . ? C26 C25 C28 121.0(4) . . ? C25 C26 C27 121.2(3) . . ? C22 C27 C26 119.9(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.668 _refine_diff_density_min -0.535 _refine_diff_density_rms 0.108 _database_code_depnum_ccdc_archive 'CCDC 957293' ####################################################################### # # 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_Compound3 # data_d389jj _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H19 N O4 Zn' _chemical_formula_weight 426.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2441(10) _cell_length_b 11.3889(13) _cell_length_c 11.8203(15) _cell_angle_alpha 67.142(5) _cell_angle_beta 72.808(5) _cell_angle_gamma 77.218(5) _cell_volume 969.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9889 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 27.93 _exptl_crystal_description thin_Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not Measured' _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 1.294 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8815 _exptl_absorpt_correction_T_max 0.9501 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CMOS Area Detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39075 _diffrn_reflns_av_R_equivalents 0.0636 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4458 _reflns_number_gt 3842 _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, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0150P)^2^+1.2184P] 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 4458 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0626 _refine_ls_wR_factor_gt 0.0596 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 0.41880(3) 0.47552(2) 0.41838(2) 0.01167(6) Uani 1 1 d . . . O1 O 0.24626(18) 0.60628(13) 0.48232(14) 0.0226(3) Uani 1 1 d . . . O2 O 0.36825(17) 0.64978(13) 0.60449(15) 0.0228(3) Uani 1 1 d . . . O3 O 0.56635(19) 0.62065(13) 0.29877(14) 0.0242(3) Uani 1 1 d . . . O4 O 0.68322(19) 0.66701(13) 0.42186(13) 0.0226(3) Uani 1 1 d . . . N1 N 0.3039(2) 0.47223(14) 0.28947(15) 0.0137(3) Uani 1 1 d . . . C1 C 0.3899(3) 0.4190(2) 0.2026(2) 0.0230(4) Uani 1 1 d . . . H1 H 0.5047 0.3813 0.2035 0.028 Uiso 1 1 calc R . . C2 C 0.3187(3) 0.4167(2) 0.1119(2) 0.0256(5) Uani 1 1 d . . . H2 H 0.3842 0.3781 0.0517 0.031 Uiso 1 1 calc R . . C3 C 0.1503(3) 0.47115(18) 0.10849(19) 0.0179(4) Uani 1 1 d . . . C4 C 0.0606(2) 0.52352(18) 0.20139(18) 0.0160(4) Uani 1 1 d . . . H4 H -0.0556 0.5594 0.2045 0.019 Uiso 1 1 calc R . . C5 C 0.1405(2) 0.52312(17) 0.28856(18) 0.0148(4) Uani 1 1 d . . . H5 H 0.0778 0.5602 0.3505 0.018 Uiso 1 1 calc R . . C6 C 0.0768(3) 0.4724(2) 0.0090(2) 0.0216(4) Uani 1 1 d . . . H6 H 0.1456 0.4299 -0.0472 0.026 Uiso 1 1 calc R . . C7 C 0.2471(2) 0.66358(17) 0.55396(18) 0.0148(4) Uani 1 1 d . . . C8 C 0.0925(2) 0.75518(17) 0.58114(18) 0.0144(4) Uani 1 1 d . . . C9 C 0.0899(2) 0.83047(18) 0.65048(19) 0.0179(4) Uani 1 1 d . . . H9 H 0.1871 0.8239 0.6811 0.021 Uiso 1 1 calc R . . C10 C -0.0540(3) 0.91521(19) 0.6752(2) 0.0202(4) Uani 1 1 d . . . H10 H -0.0534 0.9671 0.7215 0.024 Uiso 1 1 calc R . . C11 C -0.1988(3) 0.92518(18) 0.63313(19) 0.0191(4) Uani 1 1 d . . . C12 C -0.1961(3) 0.84798(19) 0.5653(2) 0.0198(4) Uani 1 1 d . . . H12 H -0.2948 0.8522 0.5374 0.024 Uiso 1 1 calc R . . C13 C -0.0517(2) 0.76508(18) 0.53798(19) 0.0166(4) Uani 1 1 d . . . H13 H -0.0512 0.7149 0.4897 0.020 Uiso 1 1 calc R . . C14 C -0.3551(3) 1.0164(2) 0.6608(2) 0.0283(5) Uani 1 1 d . . . H14A H -0.4382 0.9695 0.7345 0.042 Uiso 1 1 calc R . . H14B H -0.4065 1.0551 0.5876 0.042 Uiso 1 1 calc R . . H14C H -0.3223 1.0841 0.6784 0.042 Uiso 1 1 calc R . . C15 C 0.6471(2) 0.68909(17) 0.31909(18) 0.0150(4) Uani 1 1 d . . . C16 C 0.7019(2) 0.80819(17) 0.21175(18) 0.0150(4) Uani 1 1 d . . . C17 C 0.7723(2) 0.89799(18) 0.2300(2) 0.0184(4) Uani 1 1 d . . . H17 H 0.7986 0.8797 0.3086 0.022 Uiso 1 1 calc R . . C18 C 0.8040(3) 1.01393(19) 0.1338(2) 0.0228(4) Uani 1 1 d . . . H18 H 0.8512 1.0748 0.1476 0.027 Uiso 1 1 calc R . . C19 C 0.7683(3) 1.04307(19) 0.0176(2) 0.0237(5) Uani 1 1 d . . . C20 C 0.7052(3) 0.9507(2) -0.0018(2) 0.0250(5) Uani 1 1 d . . . H20 H 0.6854 0.9670 -0.0821 0.030 Uiso 1 1 calc R . . C21 C 0.6709(3) 0.83506(19) 0.09454(19) 0.0196(4) Uani 1 1 d . . . H21 H 0.6256 0.7736 0.0802 0.024 Uiso 1 1 calc R . . C22 C 0.7947(3) 1.1729(2) -0.0839(2) 0.0363(6) Uani 1 1 d . . . H22A H 0.7907 1.1699 -0.1647 0.054 Uiso 1 1 calc R . . H22B H 0.9063 1.1954 -0.0910 0.054 Uiso 1 1 calc R . . H22C H 0.7042 1.2377 -0.0617 0.054 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 0.01173(10) 0.01276(10) 0.01386(11) -0.00592(8) -0.00649(8) -0.00082(7) O1 0.0249(8) 0.0234(7) 0.0253(8) -0.0160(6) -0.0122(6) 0.0081(6) O2 0.0161(7) 0.0236(7) 0.0370(9) -0.0179(7) -0.0129(7) 0.0044(6) O3 0.0284(8) 0.0212(7) 0.0247(8) -0.0012(6) -0.0104(7) -0.0130(6) O4 0.0301(8) 0.0217(7) 0.0163(7) -0.0018(6) -0.0070(6) -0.0102(6) N1 0.0140(8) 0.0145(7) 0.0147(8) -0.0047(6) -0.0054(6) -0.0038(6) C1 0.0161(10) 0.0329(11) 0.0263(12) -0.0172(10) -0.0098(9) 0.0041(8) C2 0.0201(11) 0.0402(13) 0.0261(12) -0.0234(10) -0.0111(9) 0.0073(9) C3 0.0199(10) 0.0203(9) 0.0180(10) -0.0078(8) -0.0093(8) -0.0027(8) C4 0.0154(9) 0.0170(9) 0.0182(10) -0.0063(8) -0.0081(8) -0.0008(7) C5 0.0152(9) 0.0153(9) 0.0163(10) -0.0068(8) -0.0065(8) -0.0005(7) C6 0.0216(10) 0.0298(11) 0.0211(11) -0.0157(9) -0.0096(9) 0.0008(8) C7 0.0156(9) 0.0116(8) 0.0151(10) -0.0028(7) -0.0031(8) -0.0015(7) C8 0.0130(9) 0.0123(8) 0.0160(10) -0.0034(7) -0.0028(7) -0.0011(7) C9 0.0150(9) 0.0194(9) 0.0217(11) -0.0097(8) -0.0045(8) -0.0019(8) C10 0.0208(10) 0.0192(10) 0.0221(11) -0.0108(9) -0.0036(9) -0.0002(8) C11 0.0166(10) 0.0178(9) 0.0175(10) -0.0039(8) -0.0012(8) 0.0004(8) C12 0.0148(9) 0.0219(10) 0.0213(11) -0.0051(8) -0.0063(8) -0.0012(8) C13 0.0168(9) 0.0158(9) 0.0179(10) -0.0055(8) -0.0055(8) -0.0019(7) C14 0.0208(11) 0.0307(12) 0.0273(12) -0.0111(10) -0.0029(9) 0.0072(9) C15 0.0108(9) 0.0142(9) 0.0185(10) -0.0062(8) -0.0029(8) 0.0016(7) C16 0.0103(9) 0.0149(9) 0.0170(10) -0.0050(8) -0.0012(7) 0.0002(7) C17 0.0140(9) 0.0207(10) 0.0214(11) -0.0085(8) -0.0037(8) -0.0018(8) C18 0.0165(10) 0.0182(10) 0.0325(13) -0.0085(9) -0.0024(9) -0.0045(8) C19 0.0163(10) 0.0186(10) 0.0252(12) -0.0012(9) 0.0019(9) -0.0016(8) C20 0.0232(11) 0.0298(11) 0.0169(11) -0.0039(9) -0.0038(9) -0.0019(9) C21 0.0191(10) 0.0199(10) 0.0200(11) -0.0070(8) -0.0046(8) -0.0024(8) C22 0.0288(13) 0.0238(11) 0.0369(14) 0.0040(10) 0.0001(11) -0.0030(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 2.0254(13) 2_666 ? Zn1 O1 2.0283(13) . ? Zn1 N1 2.0330(15) . ? Zn1 O4 2.0475(14) 2_666 ? Zn1 O3 2.0659(14) . ? Zn1 Zn1 2.9189(5) 2_666 ? O1 C7 1.256(2) . ? O2 C7 1.260(2) . ? O2 Zn1 2.0254(13) 2_666 ? O3 C15 1.256(2) . ? O4 C15 1.253(2) . ? O4 Zn1 2.0475(14) 2_666 ? N1 C1 1.337(2) . ? N1 C5 1.345(2) . ? C1 C2 1.377(3) . ? C1 H1 0.9500 . ? C2 C3 1.395(3) . ? C2 H2 0.9500 . ? C3 C4 1.394(3) . ? C3 C6 1.467(3) . ? C4 C5 1.376(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C6 1.323(4) 2_565 ? C6 H6 0.9500 . ? C7 C8 1.499(2) . ? C8 C9 1.391(3) . ? C8 C13 1.394(3) . ? C9 C10 1.390(3) . ? C9 H9 0.9500 . ? C10 C11 1.390(3) . ? C10 H10 0.9500 . ? C11 C12 1.395(3) . ? C11 C14 1.507(3) . ? C12 C13 1.387(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.500(3) . ? C16 C21 1.387(3) . ? C16 C17 1.392(3) . ? C17 C18 1.384(3) . ? C17 H17 0.9500 . ? C18 C19 1.387(3) . ? C18 H18 0.9500 . ? C19 C20 1.390(3) . ? C19 C22 1.511(3) . ? C20 C21 1.386(3) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? 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 O1 160.34(5) 2_666 . ? O2 Zn1 N1 100.91(6) 2_666 . ? O1 Zn1 N1 98.70(6) . . ? O2 Zn1 O4 88.13(6) 2_666 2_666 ? O1 Zn1 O4 88.98(6) . 2_666 ? N1 Zn1 O4 102.34(6) . 2_666 ? O2 Zn1 O3 87.31(6) 2_666 . ? O1 Zn1 O3 88.95(6) . . ? N1 Zn1 O3 97.19(6) . . ? O4 Zn1 O3 160.45(5) 2_666 . ? O2 Zn1 Zn1 84.24(4) 2_666 2_666 ? O1 Zn1 Zn1 76.15(4) . 2_666 ? N1 Zn1 Zn1 170.82(4) . 2_666 ? O4 Zn1 Zn1 85.31(4) 2_666 2_666 ? O3 Zn1 Zn1 75.31(4) . 2_666 ? C7 O1 Zn1 132.63(13) . . ? C7 O2 Zn1 122.06(12) . 2_666 ? C15 O3 Zn1 132.29(14) . . ? C15 O4 Zn1 120.58(13) . 2_666 ? C1 N1 C5 118.06(16) . . ? C1 N1 Zn1 120.48(13) . . ? C5 N1 Zn1 121.46(12) . . ? N1 C1 C2 122.60(18) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 119.95(19) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 116.93(17) . . ? C4 C3 C6 123.31(18) . . ? C2 C3 C6 119.76(18) . . ? C5 C4 C3 119.86(17) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N1 C5 C4 122.57(17) . . ? N1 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? C6 C6 C3 125.6(2) 2_565 . ? C6 C6 H6 117.2 2_565 . ? C3 C6 H6 117.2 . . ? O1 C7 O2 124.87(17) . . ? O1 C7 C8 117.43(17) . . ? O2 C7 C8 117.70(16) . . ? C9 C8 C13 119.05(17) . . ? C9 C8 C7 120.77(17) . . ? C13 C8 C7 120.18(17) . . ? C10 C9 C8 120.39(18) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 120.95(18) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C10 C11 C12 118.32(18) . . ? C10 C11 C14 120.86(18) . . ? C12 C11 C14 120.82(19) . . ? C13 C12 C11 121.09(18) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C8 120.18(18) . . ? C12 C13 H13 119.9 . . ? C8 C13 H13 119.9 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O4 C15 O3 125.43(18) . . ? O4 C15 C16 117.55(17) . . ? O3 C15 C16 117.01(17) . . ? C21 C16 C17 118.86(18) . . ? C21 C16 C15 120.03(17) . . ? C17 C16 C15 120.92(18) . . ? C18 C17 C16 120.09(19) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 121.33(19) . . ? C17 C18 H18 119.3 . . ? C19 C18 H18 119.3 . . ? C18 C19 C20 118.26(19) . . ? C18 C19 C22 120.6(2) . . ? C20 C19 C22 121.2(2) . . ? C21 C20 C19 120.7(2) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C20 C21 C16 120.62(19) . . ? C20 C21 H21 119.7 . . ? C16 C21 H21 119.7 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.410 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.067 _database_code_depnum_ccdc_archive 'CCDC 957294' ####################################################################### # # 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_compound4 # data_d156jj _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24 N2 O4 Zn' _chemical_formula_weight 517.86 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.208(7) _cell_length_b 10.368(7) _cell_length_c 11.703(8) _cell_angle_alpha 87.864(12) _cell_angle_beta 74.045(12) _cell_angle_gamma 81.843(12) _cell_volume 1178.8(13) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 888 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 26.83 _exptl_crystal_description Thin_Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 1.080 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6142 _exptl_absorpt_correction_T_max 0.8997 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13686 _diffrn_reflns_av_R_equivalents 0.0587 _diffrn_reflns_av_sigmaI/netI 0.0800 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5400 _reflns_number_gt 3969 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0688P)^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 5400 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0775 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1267 _refine_ls_wR_factor_gt 0.1166 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 0.59077(4) 0.60503(3) 0.60377(3) 0.01492(12) Uani 1 1 d . . . O1 O 0.6982(2) 0.7574(2) 0.66223(19) 0.0202(5) Uani 1 1 d . . . O2 O 0.5416(2) 0.6569(2) 0.7856(2) 0.0208(5) Uani 1 1 d . . . O3 O 0.4579(2) 0.4685(2) 0.6379(2) 0.0208(5) Uani 1 1 d . . . O4 O 0.3073(2) 0.3831(2) 0.56920(19) 0.0196(5) Uani 1 1 d . . . N1 N 0.7483(3) 0.4447(2) 0.6215(2) 0.0171(6) Uani 1 1 d . . . C1 C 0.7148(3) 0.3537(3) 0.7041(3) 0.0200(7) Uani 1 1 d . . . H1 H 0.6358 0.3739 0.7694 0.024 Uiso 1 1 calc R . . C2 C 0.7908(3) 0.2310(3) 0.6984(3) 0.0182(7) Uani 1 1 d . . . H2 H 0.7631 0.1688 0.7587 0.022 Uiso 1 1 calc R . . C3 C 0.9078(3) 0.1989(3) 0.6040(3) 0.0148(6) Uani 1 1 d . . . C4 C 0.9486(3) 0.2980(3) 0.5254(3) 0.0160(6) Uani 1 1 d . . . H4 H 1.0327 0.2842 0.4644 0.019 Uiso 1 1 calc R . . C5 C 0.8652(3) 0.4183(3) 0.5363(3) 0.0181(7) Uani 1 1 d . . . H5 H 0.8933 0.4845 0.4802 0.022 Uiso 1 1 calc R . . N2 N 0.5690(3) 0.2438(2) 0.4221(2) 0.0161(5) Uani 1 1 d . . . C6 C 0.5433(3) 0.1568(3) 0.5100(3) 0.0178(6) Uani 1 1 d . . . H6 H 0.4511 0.1570 0.5570 0.021 Uiso 1 1 calc R . . C7 C 0.6447(3) 0.0665(3) 0.5356(3) 0.0169(6) Uani 1 1 d . . . H7 H 0.6215 0.0061 0.5986 0.020 Uiso 1 1 calc R . . C8 C 0.7814(3) 0.0644(3) 0.4688(3) 0.0148(6) Uani 1 1 d . . . C9 C 0.8053(3) 0.1528(3) 0.3756(3) 0.0164(6) Uani 1 1 d . . . H9 H 0.8959 0.1536 0.3256 0.020 Uiso 1 1 calc R . . C10 C 0.6982(3) 0.2394(3) 0.3554(3) 0.0159(6) Uani 1 1 d . . . H10 H 0.7175 0.2984 0.2908 0.019 Uiso 1 1 calc R . . C11 C 0.9672(3) 0.0585(3) 0.5839(3) 0.0136(6) Uani 1 1 d . . . H11 H 0.9656 0.0138 0.6613 0.016 Uiso 1 1 calc R . . C12 C 0.8927(3) -0.0185(3) 0.5088(3) 0.0146(6) Uani 1 1 d . . . H12 H 0.8577 -0.0963 0.5536 0.017 Uiso 1 1 calc R . . C13 C 0.6258(3) 0.7386(3) 0.7653(3) 0.0163(6) Uani 1 1 d . . . C14 C 0.6375(3) 0.8149(3) 0.8671(3) 0.0175(6) Uani 1 1 d . . . C15 C 0.7340(3) 0.9000(3) 0.8488(3) 0.0213(7) Uani 1 1 d . . . H15 H 0.7893 0.9135 0.7707 0.026 Uiso 1 1 calc R . . C16 C 0.7506(4) 0.9658(3) 0.9436(3) 0.0239(7) Uani 1 1 d . . . H16 H 0.8174 1.0239 0.9297 0.029 Uiso 1 1 calc R . . C17 C 0.6712(4) 0.9481(3) 1.0582(3) 0.0258(8) Uani 1 1 d . . . C18 C 0.5724(3) 0.8648(3) 1.0755(3) 0.0241(7) Uani 1 1 d . . . H18 H 0.5152 0.8535 1.1533 0.029 Uiso 1 1 calc R . . C19 C 0.5559(3) 0.7986(3) 0.9823(3) 0.0199(7) Uani 1 1 d . . . H19 H 0.4885 0.7412 0.9963 0.024 Uiso 1 1 calc R . . C20 C 0.6915(4) 1.0182(4) 1.1611(3) 0.0360(9) Uani 1 1 d . . . H20A H 0.6623 0.9680 1.2340 0.054 Uiso 1 1 calc R . . H20B H 0.6365 1.1046 1.1700 0.054 Uiso 1 1 calc R . . H20C H 0.7889 1.0277 1.1462 0.054 Uiso 1 1 calc R . . C21 C 0.3510(3) 0.4189(3) 0.6521(3) 0.0158(6) Uani 1 1 d . . . C22 C 0.2670(3) 0.3990(3) 0.7764(3) 0.0242(8) Uani 1 1 d . . . C23 C 0.2953(4) 0.4555(3) 0.8711(3) 0.0284(8) Uani 1 1 d . . . H23 H 0.3692 0.5057 0.8564 0.034 Uiso 1 1 calc R . . C24 C 0.2178(4) 0.4397(4) 0.9860(3) 0.0385(10) Uani 1 1 d . . . H24 H 0.2377 0.4801 1.0497 0.046 Uiso 1 1 calc R . . C25 C 0.1119(4) 0.3660(4) 1.0088(4) 0.0424(11) Uani 1 1 d . . . C26 C 0.0818(4) 0.3092(4) 0.9163(4) 0.0442(11) Uani 1 1 d . . . H26 H 0.0088 0.2578 0.9323 0.053 Uiso 1 1 calc R . . C27 C 0.1586(4) 0.3268(3) 0.7978(4) 0.0329(9) Uani 1 1 d . . . H27 H 0.1362 0.2897 0.7338 0.040 Uiso 1 1 calc R . . C28 C 0.0252(5) 0.3474(5) 1.1351(4) 0.0640(16) Uani 1 1 d . . . H28A H -0.0402 0.4264 1.1612 0.096 Uiso 1 1 calc R . . H28B H 0.0852 0.3307 1.1881 0.096 Uiso 1 1 calc R . . H28C H -0.0253 0.2733 1.1375 0.096 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 0.01135(19) 0.01204(18) 0.0211(2) -0.00191(13) -0.00747(14) 0.00594(12) O1 0.0204(12) 0.0217(11) 0.0180(12) -0.0011(9) -0.0071(10) 0.0034(9) O2 0.0196(12) 0.0165(11) 0.0270(13) -0.0010(9) -0.0092(10) 0.0009(9) O3 0.0163(12) 0.0181(11) 0.0271(13) 0.0007(9) -0.0059(10) 0.0008(9) O4 0.0138(11) 0.0210(11) 0.0231(12) -0.0012(9) -0.0068(9) 0.0044(9) N1 0.0131(13) 0.0106(12) 0.0266(15) -0.0019(10) -0.0070(11) 0.0049(10) C1 0.0191(16) 0.0173(15) 0.0209(17) -0.0028(12) -0.0060(13) 0.0085(13) C2 0.0183(16) 0.0166(15) 0.0173(16) 0.0001(12) -0.0051(13) 0.0064(12) C3 0.0119(15) 0.0136(14) 0.0205(16) -0.0025(12) -0.0092(12) 0.0026(11) C4 0.0087(14) 0.0129(14) 0.0246(17) -0.0016(12) -0.0045(12) 0.0048(11) C5 0.0124(15) 0.0117(14) 0.0323(19) 0.0014(12) -0.0112(14) 0.0016(11) N2 0.0147(13) 0.0145(12) 0.0199(14) -0.0019(10) -0.0088(11) 0.0045(10) C6 0.0111(15) 0.0160(15) 0.0258(17) -0.0025(12) -0.0056(13) 0.0014(12) C7 0.0142(15) 0.0126(14) 0.0232(17) 0.0001(12) -0.0056(13) 0.0018(12) C8 0.0139(15) 0.0113(14) 0.0200(16) -0.0021(11) -0.0082(12) 0.0039(11) C9 0.0112(14) 0.0148(14) 0.0207(16) -0.0006(12) -0.0029(12) 0.0039(11) C10 0.0158(15) 0.0134(14) 0.0196(16) 0.0001(11) -0.0086(13) 0.0021(12) C11 0.0100(14) 0.0111(13) 0.0186(15) 0.0005(11) -0.0043(12) 0.0033(11) C12 0.0118(14) 0.0112(13) 0.0203(16) 0.0002(11) -0.0066(12) 0.0040(11) C13 0.0147(15) 0.0113(14) 0.0216(17) -0.0017(12) -0.0082(13) 0.0088(12) C14 0.0163(15) 0.0142(14) 0.0214(17) -0.0017(12) -0.0088(13) 0.0076(12) C15 0.0234(17) 0.0177(15) 0.0212(17) 0.0026(12) -0.0069(14) 0.0034(13) C16 0.0286(19) 0.0171(16) 0.0306(19) 0.0002(13) -0.0188(16) 0.0031(13) C17 0.031(2) 0.0209(16) 0.0260(19) -0.0054(13) -0.0169(16) 0.0142(14) C18 0.0258(18) 0.0245(17) 0.0187(17) -0.0007(13) -0.0081(14) 0.0119(14) C19 0.0168(16) 0.0173(15) 0.0239(17) 0.0004(12) -0.0063(13) 0.0054(12) C20 0.045(2) 0.032(2) 0.033(2) -0.0106(16) -0.0219(19) 0.0114(17) C21 0.0156(15) 0.0093(13) 0.0191(16) 0.0013(11) -0.0046(13) 0.0089(11) C22 0.0164(16) 0.0198(16) 0.0279(19) 0.0069(13) -0.0002(14) 0.0124(13) C23 0.0269(19) 0.0306(18) 0.0197(18) 0.0027(14) -0.0029(15) 0.0160(15) C24 0.038(2) 0.039(2) 0.027(2) 0.0039(16) -0.0037(18) 0.0212(18) C25 0.033(2) 0.041(2) 0.036(2) 0.0138(19) 0.0038(19) 0.0241(18) C26 0.024(2) 0.041(2) 0.053(3) 0.022(2) 0.0046(19) 0.0071(17) C27 0.0196(18) 0.0288(19) 0.044(2) 0.0121(16) -0.0025(16) 0.0028(15) C28 0.049(3) 0.063(3) 0.045(3) 0.027(2) 0.020(2) 0.036(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 O4 2.014(2) 2_666 ? Zn1 O3 2.051(2) . ? Zn1 O2 2.120(3) . ? Zn1 N2 2.172(3) 2_666 ? Zn1 N1 2.189(3) . ? Zn1 O1 2.269(2) . ? Zn1 C13 2.515(3) . ? O1 C13 1.254(4) . ? O2 C13 1.262(4) . ? O3 C21 1.240(4) . ? O4 C21 1.260(4) . ? O4 Zn1 2.014(2) 2_666 ? N1 C5 1.329(4) . ? N1 C1 1.335(4) . ? C1 C2 1.387(4) . ? C2 C3 1.395(4) . ? C3 C4 1.384(4) . ? C3 C11 1.497(4) . ? C4 C5 1.396(4) . ? N2 C10 1.330(4) . ? N2 C6 1.338(4) . ? N2 Zn1 2.172(3) 2_666 ? C6 C7 1.383(4) . ? C7 C8 1.397(4) . ? C8 C9 1.390(4) . ? C8 C12 1.495(4) . ? C9 C10 1.381(4) . ? C11 C12 1.551(4) 2_756 ? C11 C12 1.605(4) . ? C12 C11 1.551(4) 2_756 ? C13 C14 1.495(4) . ? C14 C15 1.383(5) . ? C14 C19 1.395(4) . ? C15 C16 1.385(5) . ? C16 C17 1.384(5) . ? C17 C18 1.388(5) . ? C17 C20 1.506(5) . ? C18 C19 1.371(5) . ? C21 C22 1.495(4) . ? C22 C27 1.384(5) . ? C22 C23 1.388(5) . ? C23 C24 1.377(5) . ? C24 C25 1.373(6) . ? C25 C26 1.377(7) . ? C25 C28 1.521(5) . ? C26 C27 1.413(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Zn1 O3 113.52(9) 2_666 . ? O4 Zn1 O2 154.00(9) 2_666 . ? O3 Zn1 O2 92.47(9) . . ? O4 Zn1 N2 89.83(9) 2_666 2_666 ? O3 Zn1 N2 91.63(10) . 2_666 ? O2 Zn1 N2 90.16(9) . 2_666 ? O4 Zn1 N1 88.42(9) 2_666 . ? O3 Zn1 N1 85.98(10) . . ? O2 Zn1 N1 92.89(9) . . ? N2 Zn1 N1 176.19(10) 2_666 . ? O4 Zn1 O1 94.11(9) 2_666 . ? O3 Zn1 O1 152.31(9) . . ? O2 Zn1 O1 59.90(8) . . ? N2 Zn1 O1 90.22(10) 2_666 . ? N1 Zn1 O1 93.27(10) . . ? O4 Zn1 C13 123.92(10) 2_666 . ? O3 Zn1 C13 122.53(10) . . ? O2 Zn1 C13 30.08(9) . . ? N2 Zn1 C13 90.11(10) 2_666 . ? N1 Zn1 C13 93.67(10) . . ? O1 Zn1 C13 29.82(9) . . ? C13 O1 Zn1 86.01(18) . . ? C13 O2 Zn1 92.59(18) . . ? C21 O3 Zn1 160.3(2) . . ? C21 O4 Zn1 123.1(2) . 2_666 ? C5 N1 C1 117.7(3) . . ? C5 N1 Zn1 121.2(2) . . ? C1 N1 Zn1 119.2(2) . . ? N1 C1 C2 122.6(3) . . ? C1 C2 C3 120.0(3) . . ? C4 C3 C2 116.7(3) . . ? C4 C3 C11 124.2(3) . . ? C2 C3 C11 118.4(3) . . ? C3 C4 C5 119.5(3) . . ? N1 C5 C4 123.1(3) . . ? C10 N2 C6 117.5(3) . . ? C10 N2 Zn1 121.0(2) . 2_666 ? C6 N2 Zn1 121.4(2) . 2_666 ? N2 C6 C7 123.0(3) . . ? C6 C7 C8 119.9(3) . . ? C9 C8 C7 116.2(3) . . ? C9 C8 C12 124.0(3) . . ? C7 C8 C12 119.4(3) . . ? C10 C9 C8 120.4(3) . . ? N2 C10 C9 123.0(3) . . ? C3 C11 C12 120.7(2) . 2_756 ? C3 C11 C12 113.4(2) . . ? C12 C11 C12 89.9(2) 2_756 . ? C8 C12 C11 118.5(3) . 2_756 ? C8 C12 C11 114.2(2) . . ? C11 C12 C11 90.1(2) 2_756 . ? O1 C13 O2 121.5(3) . . ? O1 C13 C14 119.8(3) . . ? O2 C13 C14 118.6(3) . . ? O1 C13 Zn1 64.17(17) . . ? O2 C13 Zn1 57.34(16) . . ? C14 C13 Zn1 175.9(2) . . ? C15 C14 C19 118.7(3) . . ? C15 C14 C13 120.0(3) . . ? C19 C14 C13 121.2(3) . . ? C14 C15 C16 120.4(3) . . ? C17 C16 C15 120.9(3) . . ? C16 C17 C18 118.4(3) . . ? C16 C17 C20 120.6(3) . . ? C18 C17 C20 121.0(3) . . ? C19 C18 C17 121.1(3) . . ? C18 C19 C14 120.5(3) . . ? O3 C21 O4 124.9(3) . . ? O3 C21 C22 118.1(3) . . ? O4 C21 C22 117.0(3) . . ? C27 C22 C23 119.5(3) . . ? C27 C22 C21 120.4(3) . . ? C23 C22 C21 120.1(3) . . ? C24 C23 C22 120.9(4) . . ? C25 C24 C23 120.3(4) . . ? C24 C25 C26 119.9(4) . . ? C24 C25 C28 121.0(5) . . ? C26 C25 C28 119.1(5) . . ? C25 C26 C27 120.5(4) . . ? C22 C27 C26 119.0(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.268 _refine_diff_density_min -0.863 _refine_diff_density_rms 0.121 #===#END _database_code_depnum_ccdc_archive 'CCDC 957295'