Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'En-Qing Gao' _publ_contact_author_address ; Department of Chemistry East China Normal University Shanghai 200062 CHINA ; _publ_contact_author_email EQGAO@CHEM.ECNU.EDU.CN _publ_section_title ; Towards tuning the packing and entanglement of zigzag coordination chains by terminal ligands ; loop_ _publ_author_name 'En-Qing Gao.' 'Ai-Ling Cheng.' 'Yu Ma.' 'Jian-Yong Zhang.' data_1 _database_code_depnum_ccdc_archive 'CCDC 654224' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H25 N3 O4 Zn' _chemical_formula_weight 568.91 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 15.196(4) _cell_length_b 6.2989(17) _cell_length_c 15.096(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.592(4) _cell_angle_gamma 90.00 _cell_volume 1420.3(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 772 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 19.13 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 588 _exptl_absorpt_coefficient_mu 0.904 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8993 _exptl_absorpt_correction_T_max 0.9477 _exptl_absorpt_process_details SADABS _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 '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 6704 _diffrn_reflns_av_R_equivalents 0.1068 _diffrn_reflns_av_sigmaI/netI 0.1684 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2545 _reflns_number_gt 1075 _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^)+(0.0123P)^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 2545 _refine_ls_number_parameters 218 _refine_ls_number_restraints 37 _refine_ls_R_factor_all 0.1486 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1150 _refine_ls_wR_factor_gt 0.0897 _refine_ls_goodness_of_fit_ref 0.838 _refine_ls_restrained_S_all 0.843 _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 0.5000 0.62220(12) 0.7500 0.0551(3) Uani 1 2 d S . . O1 O 0.40735(19) 0.4207(5) 0.6993(2) 0.0710(10) Uani 1 1 d . A . O2 O 0.3504(2) 0.6982(6) 0.6197(3) 0.0903(13) Uani 1 1 d . A . N1 N 0.4392(3) 0.8159(6) 0.8290(3) 0.0595(11) Uani 1 1 d . . . C1 C 0.3470(3) 0.5091(9) 0.6422(4) 0.0600(13) Uani 1 1 d . . . C4 C 0.2603(10) 0.163(2) 0.6505(15) 0.065(5) Uani 0.54(4) 1 d PGU A 1 H4 H 0.3070 0.1102 0.6934 0.078 Uiso 0.54(4) 1 calc PR A 1 C2 C 0.2649(10) 0.368(2) 0.6173(15) 0.042(4) Uani 0.54(4) 1 d PGU A 1 C3 C 0.1950(11) 0.447(2) 0.5533(14) 0.055(4) Uani 0.54(4) 1 d PGU A 1 H3 H 0.1981 0.5837 0.5311 0.066 Uiso 0.54(4) 1 calc PR A 1 C5 C 0.1204(9) 0.321(3) 0.5226(13) 0.061(4) Uani 0.54(4) 1 d PGU A 1 H5 H 0.0737 0.3740 0.4798 0.073 Uiso 0.54(4) 1 calc PR A 1 C7 C 0.1158(9) 0.116(3) 0.5558(14) 0.055(4) Uani 0.54(4) 1 d PGU A 1 C6 C 0.1857(11) 0.037(2) 0.6198(15) 0.062(4) Uani 0.54(4) 1 d PGU A 1 H6 H 0.1826 -0.0996 0.6420 0.074 Uiso 0.54(4) 1 calc PR A 1 C8 C 0.0366(11) -0.017(4) 0.5286(15) 0.071(6) Uani 0.54(4) 1 d PU . 1 H8 H 0.0392 -0.1483 0.5572 0.085 Uiso 0.54(4) 1 calc PR A 1 C2' C 0.2629(11) 0.396(3) 0.5948(17) 0.046(5) Uani 0.46(4) 1 d PGU A 2 C4' C 0.2486(11) 0.190(3) 0.6222(15) 0.049(4) Uani 0.46(4) 1 d PGU A 2 H4' H 0.2926 0.1211 0.6630 0.059 Uiso 0.46(4) 1 calc PR A 2 C6' C 0.1684(13) 0.088(3) 0.5886(15) 0.055(4) Uani 0.46(4) 1 d PGU A 2 H6' H 0.1588 -0.0501 0.6070 0.066 Uiso 0.46(4) 1 calc PR A 2 C7' C 0.1026(10) 0.191(4) 0.5276(13) 0.055(5) Uani 0.46(4) 1 d PGU A 2 C5' C 0.1169(10) 0.396(4) 0.5002(14) 0.060(4) Uani 0.46(4) 1 d PGU A 2 H5' H 0.0729 0.4655 0.4594 0.072 Uiso 0.46(4) 1 calc PR A 2 C3' C 0.1971(12) 0.499(3) 0.5338(17) 0.061(5) Uani 0.46(4) 1 d PGU A 2 H3' H 0.2067 0.6367 0.5154 0.074 Uiso 0.46(4) 1 calc PR A 2 C8' C 0.0158(14) 0.090(5) 0.4870(16) 0.075(6) Uani 0.46(4) 1 d PU . 2 H8' H -0.0193 0.1607 0.4390 0.090 Uiso 0.46(4) 1 calc PR A 2 C9 C 0.3612(4) 0.7604(9) 0.8491(4) 0.0856(17) Uani 1 1 d . . . H9 H 0.3364 0.6304 0.8287 0.103 Uiso 1 1 calc R . . C10 C 0.3154(5) 0.8876(15) 0.8991(5) 0.115(2) Uani 1 1 d . . . H10 H 0.2602 0.8459 0.9114 0.138 Uiso 1 1 calc R . . C11 C 0.3525(5) 1.0753(14) 0.9300(4) 0.112(2) Uani 1 1 d . . . H11 H 0.3235 1.1625 0.9652 0.134 Uiso 1 1 calc R . . C12 C 0.4323(5) 1.1359(11) 0.9095(4) 0.0909(17) Uani 1 1 d . . . H12 H 0.4579 1.2658 0.9289 0.109 Uiso 1 1 calc R . . C13 C 0.4739(3) 0.9997(9) 0.8592(3) 0.0665(14) Uani 1 1 d . . . H13 H 0.5291 1.0390 0.8458 0.080 Uiso 1 1 calc R . . N2 N 0.0000 0.300(3) 0.2500 0.317(19) Uani 1 2 d SD . . C14 C 0.0775(13) 0.399(3) 0.2583(13) 0.304(11) Uani 1 1 d D . . H14 H 0.1303 0.3224 0.2606 0.365 Uiso 1 1 calc R . . C15 C 0.0792(6) 0.616(3) 0.2635(14) 0.331(14) Uani 1 1 d D . . H15 H 0.1327 0.6919 0.2758 0.397 Uiso 1 1 calc R . . C16 C 0.0000 0.714(4) 0.2500 0.284(17) Uani 1 2 d SD . . H16 H 0.0000 0.8613 0.2500 0.340 Uiso 1 2 calc SR . . 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 0.0409(4) 0.0489(5) 0.0713(6) 0.000 -0.0008(4) 0.000 O1 0.0480(19) 0.055(2) 0.100(3) 0.0063(18) -0.0119(18) -0.0001(15) O2 0.074(3) 0.072(3) 0.112(3) 0.021(2) -0.019(2) -0.028(2) N1 0.047(2) 0.063(3) 0.068(3) 0.007(2) 0.011(2) 0.001(2) C1 0.045(3) 0.057(3) 0.075(4) -0.005(3) 0.005(3) -0.012(3) C4 0.051(7) 0.061(7) 0.074(13) 0.020(7) -0.010(6) -0.012(5) C2 0.042(6) 0.042(7) 0.041(9) -0.001(7) 0.005(4) 0.007(5) C3 0.063(8) 0.043(7) 0.055(9) 0.012(6) 0.000(6) -0.014(5) C5 0.048(6) 0.049(9) 0.077(11) 0.002(7) -0.012(6) 0.007(5) C7 0.044(7) 0.041(8) 0.074(12) -0.005(7) 0.001(6) -0.005(6) C6 0.046(7) 0.052(8) 0.081(12) 0.004(6) -0.005(7) -0.003(5) C8 0.049(7) 0.088(11) 0.068(11) -0.002(9) -0.010(7) -0.018(7) C2' 0.045(8) 0.053(9) 0.041(10) 0.010(7) 0.007(6) -0.012(7) C4' 0.049(7) 0.050(8) 0.043(10) 0.001(7) -0.005(6) 0.004(6) C6' 0.048(10) 0.048(8) 0.065(12) 0.025(7) 0.000(7) -0.010(7) C7' 0.042(7) 0.046(12) 0.072(12) -0.010(8) 0.000(6) -0.001(7) C5' 0.053(7) 0.062(11) 0.057(9) 0.013(8) -0.011(6) -0.002(7) C3' 0.037(7) 0.073(10) 0.075(12) 0.034(8) 0.013(6) -0.004(6) C8' 0.058(9) 0.088(13) 0.068(10) 0.013(10) -0.015(7) -0.019(9) C9 0.073(4) 0.097(4) 0.091(5) 0.005(3) 0.028(4) -0.007(3) C10 0.097(5) 0.161(7) 0.101(6) 0.008(6) 0.056(5) 0.013(6) C11 0.116(6) 0.149(7) 0.077(5) -0.009(5) 0.038(5) 0.054(5) C12 0.095(5) 0.097(5) 0.079(4) -0.012(4) 0.010(4) 0.020(4) C13 0.063(3) 0.066(4) 0.069(4) -0.002(3) 0.008(3) 0.010(3) N2 0.47(5) 0.291(19) 0.158(17) 0.000 -0.02(4) 0.000 C14 0.29(3) 0.50(3) 0.131(14) -0.01(3) 0.082(17) -0.04(2) C15 0.39(4) 0.45(3) 0.171(18) 0.07(3) 0.11(2) -0.05(3) C16 0.31(4) 0.35(3) 0.23(3) 0.000 0.15(4) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.945(3) . ? Zn1 O1 1.945(3) 2_656 ? Zn1 N1 2.042(4) 2_656 ? Zn1 N1 2.042(4) . ? Zn1 O2 2.761(4) 2_656 ? Zn1 O2 2.761(4) . ? Zn1 Zn1 8.923(2) 4_576 ? Zn1 Zn1 8.923(2) 4_575 ? O1 C1 1.266(5) . ? O2 C1 1.242(5) . ? N1 C13 1.318(6) . ? N1 C9 1.325(6) . ? C1 C2' 1.522(13) . ? C1 C2 1.523(11) . ? C4 C2 1.3900 . ? C4 C6 1.3900 . ? C4 H4 0.9300 . ? C2 C3 1.3900 . ? C3 C5 1.3900 . ? C3 H3 0.9300 . ? C5 C7 1.3900 . ? C5 H5 0.9300 . ? C7 C6 1.3900 . ? C7 C8 1.464(16) . ? C6 H6 0.9300 . ? C8 C8 1.29(5) 3_556 ? C8 H8 0.9300 . ? C2' C4' 1.3900 . ? C2' C3' 1.3900 . ? C4' C6' 1.3900 . ? C4' H4' 0.9300 . ? C6' C7' 1.3900 . ? C6' H6' 0.9300 . ? C7' C5' 1.3900 . ? C7' C8' 1.49(2) . ? C5' C3' 1.3900 . ? C5' H5' 0.9300 . ? C3' H3' 0.9300 . ? C8' C8' 1.32(6) 3_556 ? C8' H8' 0.9300 . ? C9 C10 1.374(8) . ? C9 H9 0.9300 . ? C10 C11 1.356(8) . ? C10 H10 0.9300 . ? C11 C12 1.359(8) . ? C11 H11 0.9300 . ? C12 C13 1.375(7) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? N2 C14 1.319(14) . ? N2 C14 1.319(14) 2 ? C14 C15 1.373(17) . ? C14 H14 0.9300 . ? C15 C16 1.332(13) . ? C15 H15 0.9300 . ? C16 C15 1.332(13) 2 ? 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 O1 Zn1 O1 98.53(19) . 2_656 ? O1 Zn1 N1 122.17(15) . 2_656 ? O1 Zn1 N1 104.33(16) 2_656 2_656 ? O1 Zn1 N1 104.33(16) . . ? O1 Zn1 N1 122.17(15) 2_656 . ? N1 Zn1 N1 106.6(2) 2_656 . ? O1 Zn1 O2 146.65(14) . 2_656 ? O1 Zn1 O2 52.49(11) 2_656 2_656 ? N1 Zn1 O2 84.87(15) 2_656 2_656 ? N1 Zn1 O2 83.23(15) . 2_656 ? O1 Zn1 O2 52.49(11) . . ? O1 Zn1 O2 146.65(14) 2_656 . ? N1 Zn1 O2 83.23(15) 2_656 . ? N1 Zn1 O2 84.87(15) . . ? O2 Zn1 O2 160.02(16) 2_656 . ? O1 Zn1 Zn1 124.64(10) . 4_576 ? O1 Zn1 Zn1 97.33(11) 2_656 4_576 ? N1 Zn1 Zn1 104.22(11) 2_656 4_576 ? N1 Zn1 Zn1 27.98(12) . 4_576 ? O2 Zn1 Zn1 55.46(8) 2_656 4_576 ? O2 Zn1 Zn1 112.46(9) . 4_576 ? O1 Zn1 Zn1 97.33(11) . 4_575 ? O1 Zn1 Zn1 124.64(10) 2_656 4_575 ? N1 Zn1 Zn1 27.98(12) 2_656 4_575 ? N1 Zn1 Zn1 104.22(11) . 4_575 ? O2 Zn1 Zn1 112.46(9) 2_656 4_575 ? O2 Zn1 Zn1 55.46(8) . 4_575 ? Zn1 Zn1 Zn1 115.53(3) 4_576 4_575 ? C1 O1 Zn1 111.2(3) . . ? C1 O2 Zn1 73.1(3) . . ? C13 N1 C9 118.1(5) . . ? C13 N1 Zn1 122.1(3) . . ? C9 N1 Zn1 119.8(4) . . ? O2 C1 O1 123.1(4) . . ? O2 C1 C2' 113.2(9) . . ? O1 C1 C2' 123.7(9) . . ? O2 C1 C2 124.5(8) . . ? O1 C1 C2 111.6(8) . . ? C2' C1 C2 14.3(13) . . ? C2 C4 C6 120.0 . . ? C2 C4 H4 120.0 . . ? C6 C4 H4 120.0 . . ? C3 C2 C4 120.0 . . ? C3 C2 C1 116.7(9) . . ? C4 C2 C1 123.2(9) . . ? C2 C3 C5 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C3 H3 120.0 . . ? C7 C5 C3 120.0 . . ? C7 C5 H5 120.0 . . ? C3 C5 H5 120.0 . . ? C5 C7 C6 120.0 . . ? C5 C7 C8 121.7(8) . . ? C6 C7 C8 118.3(8) . . ? C7 C6 C4 120.0 . . ? C7 C6 H6 120.0 . . ? C4 C6 H6 120.0 . . ? C8 C8 C7 131(3) 3_556 . ? C8 C8 H8 114.6 3_556 . ? C7 C8 H8 114.6 . . ? C4' C2' C3' 120.0 . . ? C4' C2' C1 117.5(10) . . ? C3' C2' C1 122.1(10) . . ? C6' C4' C2' 120.0 . . ? C6' C4' H4' 120.0 . . ? C2' C4' H4' 120.0 . . ? C4' C6' C7' 120.0 . . ? C4' C6' H6' 120.0 . . ? C7' C6' H6' 120.0 . . ? C5' C7' C6' 120.0 . . ? C5' C7' C8' 116.7(9) . . ? C6' C7' C8' 123.3(9) . . ? C3' C5' C7' 120.0 . . ? C3' C5' H5' 120.0 . . ? C7' C5' H5' 120.0 . . ? C5' C3' C2' 120.0 . . ? C5' C3' H3' 120.0 . . ? C2' C3' H3' 120.0 . . ? C8' C8' C7' 126(3) 3_556 . ? C8' C8' H8' 117.1 3_556 . ? C7' C8' H8' 117.1 . . ? N1 C9 C10 122.5(6) . . ? N1 C9 H9 118.7 . . ? C10 C9 H9 118.7 . . ? C11 C10 C9 118.5(7) . . ? C11 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? C10 C11 C12 119.9(6) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C13 118.1(7) . . ? C11 C12 H12 120.9 . . ? C13 C12 H12 120.9 . . ? N1 C13 C12 122.9(6) . . ? N1 C13 H13 118.6 . . ? C12 C13 H13 118.6 . . ? C14 N2 C14 123(2) . 2 ? N2 C14 C15 119.0(19) . . ? N2 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C16 C15 C14 116.3(13) . . ? C16 C15 H15 121.9 . . ? C14 C15 H15 121.9 . . ? C15 C16 C15 125(2) 2 . ? C15 C16 H16 117.4 2 . ? C15 C16 H16 117.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Zn1 O1 C1 -163.2(4) 2_656 . . . ? N1 Zn1 O1 C1 -50.2(4) 2_656 . . . ? N1 Zn1 O1 C1 70.4(4) . . . . ? O2 Zn1 O1 C1 170.0(3) 2_656 . . . ? O2 Zn1 O1 C1 -1.4(3) . . . . ? Zn1 Zn1 O1 C1 91.7(3) 4_576 . . . ? Zn1 Zn1 O1 C1 -36.4(3) 4_575 . . . ? O1 Zn1 O2 C1 1.4(3) . . . . ? O1 Zn1 O2 C1 35.7(4) 2_656 . . . ? N1 Zn1 O2 C1 141.5(3) 2_656 . . . ? N1 Zn1 O2 C1 -111.1(3) . . . . ? O2 Zn1 O2 C1 -164.7(3) 2_656 . . . ? Zn1 Zn1 O2 C1 -115.9(3) 4_576 . . . ? Zn1 Zn1 O2 C1 137.8(3) 4_575 . . . ? O1 Zn1 N1 C13 -164.9(4) . . . . ? O1 Zn1 N1 C13 85.1(4) 2_656 . . . ? N1 Zn1 N1 C13 -34.4(3) 2_656 . . . ? O2 Zn1 N1 C13 48.2(4) 2_656 . . . ? O2 Zn1 N1 C13 -115.7(4) . . . . ? Zn1 Zn1 N1 C13 54.8(3) 4_576 . . . ? Zn1 Zn1 N1 C13 -63.3(4) 4_575 . . . ? O1 Zn1 N1 C9 13.2(4) . . . . ? O1 Zn1 N1 C9 -96.8(4) 2_656 . . . ? N1 Zn1 N1 C9 143.7(4) 2_656 . . . ? O2 Zn1 N1 C9 -133.7(4) 2_656 . . . ? O2 Zn1 N1 C9 62.3(4) . . . . ? Zn1 Zn1 N1 C9 -127.2(5) 4_576 . . . ? Zn1 Zn1 N1 C9 114.8(4) 4_575 . . . ? Zn1 O2 C1 O1 -2.0(4) . . . . ? Zn1 O2 C1 C2' 177.4(12) . . . . ? Zn1 O2 C1 C2 167.3(12) . . . . ? Zn1 O1 C1 O2 3.0(6) . . . . ? Zn1 O1 C1 C2' -176.4(13) . . . . ? Zn1 O1 C1 C2 -167.6(10) . . . . ? C6 C4 C2 C3 0.0 . . . . ? C6 C4 C2 C1 -175.2(17) . . . . ? O2 C1 C2 C3 11.0(16) . . . . ? O1 C1 C2 C3 -178.6(8) . . . . ? C2' C1 C2 C3 -30(6) . . . . ? O2 C1 C2 C4 -173.6(9) . . . . ? O1 C1 C2 C4 -3.2(15) . . . . ? C2' C1 C2 C4 146(8) . . . . ? C4 C2 C3 C5 0.0 . . . . ? C1 C2 C3 C5 175.5(16) . . . . ? C2 C3 C5 C7 0.0 . . . . ? C3 C5 C7 C6 0.0 . . . . ? C3 C5 C7 C8 176.9(15) . . . . ? C5 C7 C6 C4 0.0 . . . . ? C8 C7 C6 C4 -177.0(14) . . . . ? C2 C4 C6 C7 0.0 . . . . ? C5 C7 C8 C8 3(3) . . . 3_556 ? C6 C7 C8 C8 -179.9(19) . . . 3_556 ? O2 C1 C2' C4' -173.5(10) . . . . ? O1 C1 C2' C4' 6(2) . . . . ? C2 C1 C2' C4' -29(6) . . . . ? O2 C1 C2' C3' -0.8(17) . . . . ? O1 C1 C2' C3' 178.6(9) . . . . ? C2 C1 C2' C3' 143(8) . . . . ? C3' C2' C4' C6' 0.0 . . . . ? C1 C2' C4' C6' 173(2) . . . . ? C2' C4' C6' C7' 0.0 . . . . ? C4' C6' C7' C5' 0.0 . . . . ? C4' C6' C7' C8' 178.6(19) . . . . ? C6' C7' C5' C3' 0.0 . . . . ? C8' C7' C5' C3' -178.7(17) . . . . ? C7' C5' C3' C2' 0.0 . . . . ? C4' C2' C3' C5' 0.0 . . . . ? C1 C2' C3' C5' -173(2) . . . . ? C5' C7' C8' C8' -170(2) . . . 3_556 ? C6' C7' C8' C8' 11(3) . . . 3_556 ? C13 N1 C9 C10 0.7(8) . . . . ? Zn1 N1 C9 C10 -177.5(5) . . . . ? N1 C9 C10 C11 -1.1(10) . . . . ? C9 C10 C11 C12 1.6(10) . . . . ? C10 C11 C12 C13 -1.6(10) . . . . ? C9 N1 C13 C12 -0.7(7) . . . . ? Zn1 N1 C13 C12 177.4(4) . . . . ? C11 C12 C13 N1 1.2(8) . . . . ? C14 N2 C14 C15 3.6(12) 2 . . . ? N2 C14 C15 C16 -7(2) . . . . ? C14 C15 C16 C15 3.5(12) . . . 2 ? 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 C11 H11 O2 0.93 2.45 3.205(8) 137.8 4_576 _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.907 _refine_diff_density_max 0.276 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.055 # Attachment '2.cif' ## Crystallographic Data of Complex 2 data_2 _database_code_depnum_ccdc_archive 'CCDC 654225' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28.50 H24.50 N2.50 O6 Zn' _chemical_formula_weight 563.38 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 9.7503(2) _cell_length_b 10.9197(2) _cell_length_c 15.8132(4) _cell_angle_alpha 71.339(8) _cell_angle_beta 82.4530(10) _cell_angle_gamma 67.354(8) _cell_volume 1472.08(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 15238 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 582 _exptl_absorpt_coefficient_mu 0.876 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7791 _exptl_absorpt_correction_T_max 0.8443 _exptl_absorpt_process_details '(Blessing, 1995, 1997)' _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 'NONIUS KappaCCD Diffractometer' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26473 _diffrn_reflns_av_R_equivalents 0.0580 _diffrn_reflns_av_sigmaI/netI 0.0780 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 27.51 _reflns_number_total 6735 _reflns_number_gt 4177 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0799P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6735 _refine_ls_number_parameters 387 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0933 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1249 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.980 _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 0.27823(4) 0.76563(3) 0.54949(2) 0.03655(14) Uani 1 1 d . . . C1 C 0.2163(4) 0.5385(3) 0.6948(2) 0.0468(8) Uani 1 1 d . . . C2 C 0.2760(4) 0.4023(3) 0.76512(19) 0.0424(7) Uani 1 1 d . . . C3 C 0.1806(4) 0.3478(4) 0.8221(2) 0.0668(11) Uani 1 1 d . . . H3A H 0.0786 0.3925 0.8136 0.080 Uiso 1 1 calc R . . C4 C 0.4261(4) 0.3295(3) 0.7770(2) 0.0454(8) Uani 1 1 d . . . H4A H 0.4927 0.3617 0.7374 0.054 Uiso 1 1 calc R . . C5 C 0.2341(4) 0.2286(4) 0.8912(3) 0.0701(12) Uani 1 1 d . . . H5A H 0.1671 0.1943 0.9288 0.084 Uiso 1 1 calc R . . C6 C 0.4796(4) 0.2099(3) 0.8463(2) 0.0478(8) Uani 1 1 d . . . H6A H 0.5816 0.1628 0.8530 0.057 Uiso 1 1 calc R . . C7 C 0.3836(4) 0.1583(3) 0.9064(2) 0.0465(8) Uani 1 1 d . . . C8 C 0.4324(4) 0.0347(3) 0.9846(2) 0.0542(9) Uani 1 1 d . . . H8A H 0.3592 0.0023 1.0154 0.065 Uiso 1 1 calc R . . C9 C 0.2189(3) 0.8407(3) 0.38414(19) 0.0399(7) Uani 1 1 d . . . C10 C 0.1777(3) 0.8659(3) 0.29042(18) 0.0388(7) Uani 1 1 d . . . C11 C 0.1771(3) 0.7579(3) 0.26298(19) 0.0425(7) Uani 1 1 d . . . H11A H 0.2049 0.6685 0.3023 0.051 Uiso 1 1 calc R . . C12 C 0.1355(3) 0.9987(3) 0.23086(19) 0.0419(7) Uani 1 1 d . . . H12A H 0.1374 1.0716 0.2484 0.050 Uiso 1 1 calc R . . C13 C 0.1350(4) 0.7832(3) 0.1766(2) 0.0467(8) Uani 1 1 d . . . H13A H 0.1382 0.7093 0.1582 0.056 Uiso 1 1 calc R . . C14 C 0.0907(4) 1.0234(3) 0.14584(19) 0.0442(7) Uani 1 1 d . . . H14A H 0.0617 1.1132 0.1071 0.053 Uiso 1 1 calc R . . C15 C 0.0882(3) 0.9162(3) 0.11688(19) 0.0409(7) Uani 1 1 d . . . C16 C 0.0391(4) 0.9394(3) 0.02793(19) 0.0454(7) Uani 1 1 d . . . H16A H 0.0653 0.8615 0.0083 0.055 Uiso 1 1 calc R . . C17 C 0.2086(4) 0.9721(4) 0.6569(3) 0.0693(11) Uani 1 1 d . . . H17A H 0.1123 0.9734 0.6585 0.083 Uiso 1 1 calc R . . C18 C 0.2359(5) 1.0518(5) 0.6989(3) 0.0846(14) Uani 1 1 d . . . H18A H 0.1599 1.1057 0.7286 0.102 Uiso 1 1 calc R . . C19 C 0.3761(5) 1.0510(4) 0.6965(3) 0.0791(13) Uani 1 1 d . . . H19A H 0.3972 1.1039 0.7252 0.095 Uiso 1 1 calc R . . C20 C 0.4877(4) 0.9711(4) 0.6512(2) 0.0600(9) Uani 1 1 d . . . H20A H 0.5834 0.9717 0.6476 0.072 Uiso 1 1 calc R . . C21 C 0.4535(4) 0.8895(3) 0.6110(2) 0.0421(7) Uani 1 1 d . . . C22 C 0.5648(3) 0.7957(3) 0.5650(2) 0.0409(7) Uani 1 1 d . . . C23 C 0.7126(4) 0.7798(4) 0.5582(3) 0.0633(10) Uani 1 1 d . . . H23A H 0.7463 0.8318 0.5809 0.076 Uiso 1 1 calc R . . C24 C 0.8092(4) 0.6856(5) 0.5172(3) 0.0879(14) Uani 1 1 d . . . H24A H 0.9096 0.6727 0.5124 0.106 Uiso 1 1 calc R . . C25 C 0.7574(4) 0.6105(4) 0.4832(3) 0.0763(12) Uani 1 1 d . . . H25A H 0.8216 0.5454 0.4560 0.092 Uiso 1 1 calc R . . C26 C 0.6080(4) 0.6344(3) 0.4907(2) 0.0537(9) Uani 1 1 d . . . H26A H 0.5718 0.5856 0.4666 0.064 Uiso 1 1 calc R . . N1 N 0.3132(3) 0.8924(3) 0.61361(16) 0.0430(6) Uani 1 1 d . . . N2 N 0.5123(3) 0.7244(2) 0.53106(15) 0.0381(6) Uani 1 1 d . . . O1 O 0.3081(2) 0.5814(2) 0.64342(13) 0.0428(5) Uani 1 1 d . . . O2 O 0.0794(3) 0.6015(3) 0.6920(2) 0.1023(12) Uani 1 1 d . . . O3 O 0.2082(2) 0.9423(2) 0.41026(13) 0.0451(5) Uani 1 1 d . . . O4 O 0.2629(3) 0.7183(2) 0.43523(13) 0.0485(5) Uani 1 1 d . . . O5 O 0.0435(3) 0.8337(2) 0.56984(16) 0.0515(6) Uani 1 1 d D . . H5W H -0.031(4) 0.890(4) 0.588(3) 0.101(18) Uiso 1 1 d D . . H6W H 0.028(4) 0.772(3) 0.6139(18) 0.068(12) Uiso 1 1 d D . . C27 C 0.3809(14) 0.6279(11) 0.8509(7) 0.108(4) Uani 0.50 1 d PD . . H27A H 0.3124 0.6088 0.8264 0.130 Uiso 0.50 1 calc PR . . C28 C 0.5077(14) 0.6160(8) 0.8093(5) 0.085(3) Uani 0.50 1 d PD . . H28A H 0.5274 0.5863 0.7585 0.102 Uiso 0.50 1 calc PR . . C29 C 0.6116(12) 0.6465(9) 0.8390(7) 0.123(5) Uani 0.50 1 d PD . . H29A H 0.7027 0.6390 0.8102 0.147 Uiso 0.50 1 calc PR . . C30 C 0.5714(12) 0.6907(11) 0.9174(8) 0.098(3) Uani 0.50 1 d PD . . H30A H 0.6364 0.7155 0.9405 0.118 Uiso 0.50 1 calc PR . . C31 C 0.4432(13) 0.6966(10) 0.9572(6) 0.102(4) Uani 0.50 1 d PD . . H31A H 0.4218 0.7235 1.0091 0.123 Uiso 0.50 1 calc PR . . N3 N 0.3401(10) 0.6658(9) 0.9274(6) 0.112(3) Uani 0.50 1 d PD . . O6 O 0.9398(8) 0.6466(6) 0.8667(6) 0.125(3) Uani 0.50 1 d P . . O7 O 0.0878(10) 0.6081(7) 1.0041(6) 0.152(4) Uani 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0414(2) 0.0372(2) 0.0336(2) -0.00671(13) -0.00645(14) -0.01820(15) C1 0.044(2) 0.0404(16) 0.0481(18) -0.0003(14) -0.0065(16) -0.0154(15) C2 0.0438(19) 0.0389(16) 0.0395(16) -0.0007(13) -0.0055(14) -0.0169(14) C3 0.046(2) 0.061(2) 0.071(2) 0.0170(18) -0.0064(18) -0.0242(18) C4 0.047(2) 0.0442(17) 0.0388(17) -0.0034(13) 0.0008(14) -0.0178(15) C5 0.054(2) 0.059(2) 0.074(3) 0.0191(18) -0.0024(19) -0.0273(19) C6 0.045(2) 0.0406(17) 0.0469(18) -0.0019(14) -0.0079(15) -0.0105(14) C7 0.054(2) 0.0425(17) 0.0409(17) -0.0023(13) -0.0048(15) -0.0217(15) C8 0.057(2) 0.0496(19) 0.0493(19) 0.0023(15) -0.0057(16) -0.0246(16) C9 0.0345(17) 0.0497(18) 0.0338(16) -0.0088(14) -0.0053(13) -0.0150(14) C10 0.0344(17) 0.0497(17) 0.0321(15) -0.0116(13) -0.0021(13) -0.0152(14) C11 0.048(2) 0.0395(16) 0.0366(16) -0.0068(13) -0.0089(14) -0.0134(14) C12 0.048(2) 0.0401(16) 0.0372(16) -0.0070(13) -0.0068(14) -0.0174(14) C13 0.053(2) 0.0480(18) 0.0436(18) -0.0156(14) -0.0076(15) -0.0196(15) C14 0.045(2) 0.0455(17) 0.0357(16) -0.0018(13) -0.0082(14) -0.0160(14) C15 0.0396(18) 0.0499(17) 0.0326(15) -0.0097(13) -0.0032(13) -0.0168(14) C16 0.048(2) 0.0555(18) 0.0350(16) -0.0131(13) -0.0013(14) -0.0209(15) C17 0.052(2) 0.091(3) 0.090(3) -0.060(2) 0.016(2) -0.031(2) C18 0.060(3) 0.115(4) 0.116(4) -0.085(3) 0.024(3) -0.038(3) C19 0.085(3) 0.088(3) 0.098(3) -0.066(3) 0.006(3) -0.038(2) C20 0.061(2) 0.070(2) 0.070(2) -0.0360(19) 0.0021(19) -0.0345(19) C21 0.049(2) 0.0440(17) 0.0395(16) -0.0115(13) -0.0045(14) -0.0231(15) C22 0.0408(19) 0.0423(16) 0.0417(17) -0.0117(13) -0.0050(14) -0.0164(14) C23 0.045(2) 0.078(2) 0.086(3) -0.048(2) -0.0012(19) -0.0228(18) C24 0.036(2) 0.114(4) 0.132(4) -0.070(3) -0.003(2) -0.019(2) C25 0.048(2) 0.080(3) 0.112(3) -0.059(3) 0.002(2) -0.011(2) C26 0.050(2) 0.0518(19) 0.067(2) -0.0274(17) -0.0046(18) -0.0174(16) N1 0.0413(16) 0.0507(15) 0.0436(14) -0.0197(12) 0.0004(12) -0.0194(12) N2 0.0413(15) 0.0378(13) 0.0385(13) -0.0114(10) -0.0036(11) -0.0167(11) O1 0.0431(13) 0.0397(11) 0.0386(11) -0.0006(9) -0.0029(10) -0.0159(9) O2 0.0420(17) 0.0766(18) 0.123(3) 0.0463(17) -0.0018(16) -0.0134(14) O3 0.0488(14) 0.0504(12) 0.0405(11) -0.0166(10) -0.0064(10) -0.0183(10) O4 0.0593(15) 0.0451(12) 0.0360(11) -0.0056(9) -0.0159(10) -0.0139(10) O5 0.0408(15) 0.0444(13) 0.0600(15) -0.0026(12) -0.0020(12) -0.0157(11) C27 0.173(13) 0.095(7) 0.085(7) -0.037(6) -0.051(8) -0.054(8) C28 0.172(12) 0.063(5) 0.040(4) -0.007(4) -0.018(6) -0.065(7) C29 0.107(9) 0.058(6) 0.149(11) 0.022(6) 0.031(8) -0.024(6) C30 0.102(8) 0.119(8) 0.118(9) -0.084(7) -0.003(7) -0.047(7) C31 0.167(12) 0.092(7) 0.081(7) -0.050(6) -0.017(7) -0.058(8) N3 0.135(8) 0.088(6) 0.134(8) -0.052(6) -0.008(6) -0.044(5) O6 0.110(6) 0.064(4) 0.188(8) -0.047(4) 0.074(5) -0.032(4) O7 0.173(9) 0.068(4) 0.169(8) -0.032(5) 0.077(6) -0.022(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 2.0217(18) . ? Zn1 O4 2.069(2) . ? Zn1 N1 2.100(2) . ? Zn1 O5 2.132(3) . ? Zn1 N2 2.148(2) . ? Zn1 O3 2.387(2) . ? Zn1 Zn1 5.8142(9) 2_576 ? Zn1 Zn1 7.5823(7) 2_676 ? C1 O2 1.244(4) . ? C1 O1 1.252(4) . ? C1 C2 1.494(4) . ? C2 C4 1.375(4) . ? C2 C3 1.376(4) . ? C3 C5 1.370(5) . ? C4 C6 1.374(4) . ? C5 C7 1.373(5) . ? C6 C7 1.389(4) . ? C7 C8 1.473(4) . ? C8 C8 1.308(6) 2_657 ? C9 O4 1.258(3) . ? C9 O3 1.266(3) . ? C9 C10 1.498(4) . ? C10 C11 1.383(4) . ? C10 C12 1.388(4) . ? C11 C13 1.390(4) . ? C12 C14 1.379(4) . ? C13 C15 1.391(4) . ? C14 C15 1.396(4) . ? C15 C16 1.458(4) . ? C16 C16 1.329(6) 2_575 ? C17 N1 1.335(4) . ? C17 C18 1.366(5) . ? C18 C19 1.360(6) . ? C19 C20 1.387(5) . ? C20 C21 1.399(4) . ? C21 N1 1.351(4) . ? C21 C22 1.472(4) . ? C22 N2 1.344(4) . ? C22 C23 1.377(5) . ? C23 C24 1.373(5) . ? C24 C25 1.375(5) . ? C25 C26 1.373(5) . ? C26 N2 1.335(4) . ? C27 C28 1.302(11) . ? C27 N3 1.364(10) . ? C28 C29 1.357(11) . ? C29 C30 1.427(11) . ? C30 C31 1.311(11) . ? C31 N3 1.354(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O4 101.17(8) . . ? O1 Zn1 N1 106.09(9) . . ? O4 Zn1 N1 151.36(9) . . ? O1 Zn1 O5 91.52(9) . . ? O4 Zn1 O5 92.03(10) . . ? N1 Zn1 O5 95.83(10) . . ? O1 Zn1 N2 93.61(8) . . ? O4 Zn1 N2 93.06(9) . . ? N1 Zn1 N2 76.78(9) . . ? O5 Zn1 N2 171.95(9) . . ? O1 Zn1 O3 158.41(8) . . ? O4 Zn1 O3 58.76(7) . . ? N1 Zn1 O3 95.10(9) . . ? O5 Zn1 O3 82.08(8) . . ? N2 Zn1 O3 95.25(8) . . ? O1 Zn1 Zn1 127.16(6) . 2_576 ? O4 Zn1 Zn1 88.11(6) . 2_576 ? N1 Zn1 Zn1 82.46(7) . 2_576 ? O5 Zn1 Zn1 35.82(6) . 2_576 ? N2 Zn1 Zn1 138.18(6) . 2_576 ? O3 Zn1 Zn1 50.71(5) . 2_576 ? O1 Zn1 Zn1 130.30(6) . 2_676 ? O4 Zn1 Zn1 109.80(6) . 2_676 ? N1 Zn1 Zn1 44.19(7) . 2_676 ? O5 Zn1 Zn1 124.11(7) . 2_676 ? N2 Zn1 Zn1 48.08(6) . 2_676 ? O3 Zn1 Zn1 68.79(5) . 2_676 ? Zn1 Zn1 Zn1 92.452(8) 2_576 2_676 ? O2 C1 O1 124.8(3) . . ? O2 C1 C2 117.7(3) . . ? O1 C1 C2 117.6(3) . . ? C4 C2 C3 117.9(3) . . ? C4 C2 C1 121.8(3) . . ? C3 C2 C1 120.3(3) . . ? C5 C3 C2 120.8(3) . . ? C6 C4 C2 121.2(3) . . ? C3 C5 C7 121.9(3) . . ? C4 C6 C7 121.0(3) . . ? C5 C7 C6 117.0(3) . . ? C5 C7 C8 118.8(3) . . ? C6 C7 C8 124.2(3) . . ? C8 C8 C7 127.1(4) 2_657 . ? O4 C9 O3 121.6(3) . . ? O4 C9 C10 118.7(3) . . ? O3 C9 C10 119.7(3) . . ? C11 C10 C12 119.2(3) . . ? C11 C10 C9 120.4(3) . . ? C12 C10 C9 120.4(3) . . ? C10 C11 C13 119.8(3) . . ? C14 C12 C10 120.5(3) . . ? C11 C13 C15 121.7(3) . . ? C12 C14 C15 121.3(3) . . ? C13 C15 C14 117.4(3) . . ? C13 C15 C16 120.0(3) . . ? C14 C15 C16 122.6(3) . . ? C16 C16 C15 126.5(4) 2_575 . ? N1 C17 C18 123.2(4) . . ? C19 C18 C17 118.8(4) . . ? C18 C19 C20 119.8(3) . . ? C19 C20 C21 118.7(3) . . ? N1 C21 C20 120.6(3) . . ? N1 C21 C22 116.2(3) . . ? C20 C21 C22 123.2(3) . . ? N2 C22 C23 121.9(3) . . ? N2 C22 C21 115.1(3) . . ? C23 C22 C21 123.0(3) . . ? C24 C23 C22 118.8(3) . . ? C23 C24 C25 119.9(4) . . ? C24 C25 C26 118.0(4) . . ? N2 C26 C25 123.1(3) . . ? C17 N1 C21 118.9(3) . . ? C17 N1 Zn1 124.9(2) . . ? C21 N1 Zn1 116.3(2) . . ? C26 N2 C22 118.3(3) . . ? C26 N2 Zn1 126.1(2) . . ? C22 N2 Zn1 115.6(2) . . ? C1 O1 Zn1 130.4(2) . . ? C9 O3 Zn1 82.42(16) . . ? C9 O4 Zn1 97.04(18) . . ? C28 C27 N3 125.5(8) . . ? C27 C28 C29 120.9(8) . . ? C28 C29 C30 115.4(8) . . ? C31 C30 C29 120.4(8) . . ? C30 C31 N3 123.9(8) . . ? C31 N3 C27 113.9(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C4 -175.9(4) . . . . ? O1 C1 C2 C4 3.7(5) . . . . ? O2 C1 C2 C3 2.2(5) . . . . ? O1 C1 C2 C3 -178.2(3) . . . . ? C4 C2 C3 C5 3.3(6) . . . . ? C1 C2 C3 C5 -174.9(4) . . . . ? C3 C2 C4 C6 -3.3(5) . . . . ? C1 C2 C4 C6 174.8(3) . . . . ? C2 C3 C5 C7 -0.3(7) . . . . ? C2 C4 C6 C7 0.3(5) . . . . ? C3 C5 C7 C6 -2.7(6) . . . . ? C3 C5 C7 C8 177.0(4) . . . . ? C4 C6 C7 C5 2.7(5) . . . . ? C4 C6 C7 C8 -177.0(3) . . . . ? C5 C7 C8 C8 -171.1(5) . . . 2_657 ? C6 C7 C8 C8 8.6(7) . . . 2_657 ? O4 C9 C10 C11 4.9(4) . . . . ? O3 C9 C10 C11 -174.7(3) . . . . ? O4 C9 C10 C12 -176.9(3) . . . . ? O3 C9 C10 C12 3.5(4) . . . . ? C12 C10 C11 C13 0.2(5) . . . . ? C9 C10 C11 C13 178.4(3) . . . . ? C11 C10 C12 C14 1.2(5) . . . . ? C9 C10 C12 C14 -176.9(3) . . . . ? C10 C11 C13 C15 -2.1(5) . . . . ? C10 C12 C14 C15 -0.8(5) . . . . ? C11 C13 C15 C14 2.5(5) . . . . ? C11 C13 C15 C16 -177.5(3) . . . . ? C12 C14 C15 C13 -1.1(5) . . . . ? C12 C14 C15 C16 178.9(3) . . . . ? C13 C15 C16 C16 163.4(4) . . . 2_575 ? C14 C15 C16 C16 -16.7(6) . . . 2_575 ? N1 C17 C18 C19 0.3(7) . . . . ? C17 C18 C19 C20 0.6(7) . . . . ? C18 C19 C20 C21 -1.9(6) . . . . ? C19 C20 C21 N1 2.3(5) . . . . ? C19 C20 C21 C22 -176.9(3) . . . . ? N1 C21 C22 N2 0.1(4) . . . . ? C20 C21 C22 N2 179.4(3) . . . . ? N1 C21 C22 C23 -178.9(3) . . . . ? C20 C21 C22 C23 0.4(5) . . . . ? N2 C22 C23 C24 -1.5(6) . . . . ? C21 C22 C23 C24 177.4(4) . . . . ? C22 C23 C24 C25 0.6(7) . . . . ? C23 C24 C25 C26 0.9(7) . . . . ? C24 C25 C26 N2 -1.6(6) . . . . ? C18 C17 N1 C21 0.1(6) . . . . ? C18 C17 N1 Zn1 179.1(3) . . . . ? C20 C21 N1 C17 -1.5(5) . . . . ? C22 C21 N1 C17 177.9(3) . . . . ? C20 C21 N1 Zn1 179.5(2) . . . . ? C22 C21 N1 Zn1 -1.2(3) . . . . ? O1 Zn1 N1 C17 -87.7(3) . . . . ? O4 Zn1 N1 C17 110.7(3) . . . . ? O5 Zn1 N1 C17 5.5(3) . . . . ? N2 Zn1 N1 C17 -177.7(3) . . . . ? O3 Zn1 N1 C17 88.1(3) . . . . ? Zn1 Zn1 N1 C17 38.8(3) 2_576 . . . ? Zn1 Zn1 N1 C17 140.3(3) 2_676 . . . ? O1 Zn1 N1 C21 91.2(2) . . . . ? O4 Zn1 N1 C21 -70.3(3) . . . . ? O5 Zn1 N1 C21 -175.5(2) . . . . ? N2 Zn1 N1 C21 1.3(2) . . . . ? O3 Zn1 N1 C21 -92.9(2) . . . . ? Zn1 Zn1 N1 C21 -142.2(2) 2_576 . . . ? Zn1 Zn1 N1 C21 -40.75(17) 2_676 . . . ? C25 C26 N2 C22 0.7(5) . . . . ? C25 C26 N2 Zn1 -178.3(3) . . . . ? C23 C22 N2 C26 0.9(4) . . . . ? C21 C22 N2 C26 -178.1(3) . . . . ? C23 C22 N2 Zn1 180.0(3) . . . . ? C21 C22 N2 Zn1 1.0(3) . . . . ? O1 Zn1 N2 C26 72.1(3) . . . . ? O4 Zn1 N2 C26 -29.3(3) . . . . ? N1 Zn1 N2 C26 177.8(3) . . . . ? O5 Zn1 N2 C26 -158.5(6) . . . . ? O3 Zn1 N2 C26 -88.2(3) . . . . ? Zn1 Zn1 N2 C26 -119.9(2) 2_576 . . . ? Zn1 Zn1 N2 C26 -143.4(3) 2_676 . . . ? O1 Zn1 N2 C22 -106.9(2) . . . . ? O4 Zn1 N2 C22 151.7(2) . . . . ? N1 Zn1 N2 C22 -1.22(19) . . . . ? O5 Zn1 N2 C22 22.5(7) . . . . ? O3 Zn1 N2 C22 92.8(2) . . . . ? Zn1 Zn1 N2 C22 61.1(2) 2_576 . . . ? Zn1 Zn1 N2 C22 37.60(17) 2_676 . . . ? O2 C1 O1 Zn1 6.8(5) . . . . ? C2 C1 O1 Zn1 -172.72(19) . . . . ? O4 Zn1 O1 C1 -96.8(3) . . . . ? N1 Zn1 O1 C1 92.1(3) . . . . ? O5 Zn1 O1 C1 -4.5(3) . . . . ? N2 Zn1 O1 C1 169.3(3) . . . . ? O3 Zn1 O1 C1 -76.5(4) . . . . ? Zn1 Zn1 O1 C1 -0.7(3) 2_576 . . . ? Zn1 Zn1 O1 C1 134.8(2) 2_676 . . . ? O4 C9 O3 Zn1 -4.0(3) . . . . ? C10 C9 O3 Zn1 175.7(3) . . . . ? O1 Zn1 O3 C9 -21.0(3) . . . . ? O4 Zn1 O3 C9 2.40(17) . . . . ? N1 Zn1 O3 C9 169.95(18) . . . . ? O5 Zn1 O3 C9 -94.85(18) . . . . ? N2 Zn1 O3 C9 92.79(18) . . . . ? Zn1 Zn1 O3 C9 -114.12(18) 2_576 . . . ? Zn1 Zn1 O3 C9 133.74(17) 2_676 . . . ? O3 C9 O4 Zn1 4.6(3) . . . . ? C10 C9 O4 Zn1 -175.0(2) . . . . ? O1 Zn1 O4 C9 169.00(18) . . . . ? N1 Zn1 O4 C9 -29.0(3) . . . . ? O5 Zn1 O4 C9 77.05(19) . . . . ? N2 Zn1 O4 C9 -96.71(19) . . . . ? O3 Zn1 O4 C9 -2.41(17) . . . . ? Zn1 Zn1 O4 C9 41.45(18) 2_576 . . . ? Zn1 Zn1 O4 C9 -50.48(19) 2_676 . . . ? N3 C27 C28 C29 -2.3(17) . . . . ? C27 C28 C29 C30 0.2(14) . . . . ? C28 C29 C30 C31 1.7(15) . . . . ? C29 C30 C31 N3 -1.7(18) . . . . ? C30 C31 N3 C27 -0.2(16) . . . . ? C28 C27 N3 C31 2.2(16) . . . . ? 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 C20 H20A O3 0.93 2.51 3.383(4) 157.4 2_676 C23 H23A O3 0.93 2.72 3.597(4) 158.0 2_676 C26 H26A O1 0.93 2.75 3.461(4) 133.8 2_666 O5 H6W O2 0.845(18) 1.79(2) 2.577(3) 153(4) . O5 H5W O3 0.834(19) 1.98(2) 2.788(3) 162(5) 2_576 C29 H29A O6 0.93 2.62 3.287(14) 128.7 . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.599 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.082 # Attachment '3.cif' ## Crystallographic Data of Complex 3 data_l3 _database_code_depnum_ccdc_archive 'CCDC 654226' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H22 N2 O4 Zn' _chemical_formula_weight 587.91 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.0661(6) _cell_length_b 16.9926(8) _cell_length_c 13.9772(9) _cell_angle_alpha 90.00 _cell_angle_beta 102.210(2) _cell_angle_gamma 90.00 _cell_volume 2568.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14147 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.373 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 1.002 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8248 _exptl_absorpt_correction_T_max 0.9516 _exptl_absorpt_process_details '(Blessing, 1995, 1997)' _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 'NONIUS KappaCCD Diffractometer' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33935 _diffrn_reflns_av_R_equivalents 0.1765 _diffrn_reflns_av_sigmaI/netI 0.1643 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 25.25 _reflns_number_total 4591 _reflns_number_gt 1599 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0162P)^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 4591 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2474 _refine_ls_R_factor_gt 0.0601 _refine_ls_wR_factor_ref 0.0871 _refine_ls_wR_factor_gt 0.0630 _refine_ls_goodness_of_fit_ref 0.852 _refine_ls_restrained_S_all 0.852 _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 0.63440(6) 0.56886(3) 0.73365(4) 0.0508(2) Uani 1 1 d . . . N1 N 0.7064(4) 0.4750(2) 0.6699(4) 0.0510(13) Uani 1 1 d . . . N2 N 0.6060(4) 0.6076(3) 0.5892(3) 0.0480(12) Uani 1 1 d . . . O1 O 0.5368(4) 0.4978(2) 0.8273(3) 0.0722(13) Uani 1 1 d . . . O2 O 0.4395(3) 0.5868(2) 0.7290(3) 0.0679(13) Uani 1 1 d . . . O3 O 0.7240(3) 0.64254(18) 0.8296(2) 0.0553(11) Uani 1 1 d . . . O4 O 0.8460(4) 0.6674(2) 0.7290(3) 0.0830(14) Uani 1 1 d . . . C1 C 0.4412(7) 0.5356(4) 0.7941(4) 0.0558(18) Uani 1 1 d . . . C2 C 0.3258(6) 0.5233(3) 0.8346(4) 0.0446(15) Uani 1 1 d . . . C3 C 0.2199(6) 0.5633(3) 0.7941(4) 0.0539(15) Uani 1 1 d . . . H3A H 0.2180 0.5940 0.7388 0.065 Uiso 1 1 calc R . . C4 C 0.3266(6) 0.4759(3) 0.9126(4) 0.0542(16) Uani 1 1 d . . . H4A H 0.3965 0.4463 0.9386 0.065 Uiso 1 1 calc R . . C5 C 0.1164(5) 0.5592(3) 0.8335(4) 0.0597(17) Uani 1 1 d . . . H5A H 0.0454 0.5867 0.8047 0.072 Uiso 1 1 calc R . . C6 C 0.2231(7) 0.4714(3) 0.9537(4) 0.0618(18) Uani 1 1 d . . . H6A H 0.2244 0.4392 1.0078 0.074 Uiso 1 1 calc R . . C7 C 0.1181(6) 0.5143(3) 0.9151(5) 0.0513(16) Uani 1 1 d . . . C8 C 0.0073(6) 0.5166(3) 0.9609(4) 0.0701(19) Uani 1 1 d . . . H8A H -0.0594 0.5460 0.9277 0.084 Uiso 1 1 calc R . . C9 C 0.8012(6) 0.6842(3) 0.7998(4) 0.0520(17) Uani 1 1 d . . . C10 C 0.8470(5) 0.7579(3) 0.8568(4) 0.0449(15) Uani 1 1 d . . . C11 C 0.8803(5) 0.8227(3) 0.8083(4) 0.0582(17) Uani 1 1 d . . . H11A H 0.8752 0.8201 0.7411 0.070 Uiso 1 1 calc R . . C12 C 0.8537(4) 0.7637(3) 0.9552(4) 0.0501(16) Uani 1 1 d . . . H12A H 0.8289 0.7214 0.9888 0.060 Uiso 1 1 calc R . . C13 C 0.9210(5) 0.8913(3) 0.8581(4) 0.0594(17) Uani 1 1 d . . . H13A H 0.9413 0.9344 0.8237 0.071 Uiso 1 1 calc R . . C14 C 0.8966(5) 0.8313(3) 1.0055(4) 0.0525(16) Uani 1 1 d . . . H14A H 0.9020 0.8329 1.0728 0.063 Uiso 1 1 calc R . . C15 C 0.9320(5) 0.8968(3) 0.9595(4) 0.0475(15) Uani 1 1 d . . . C16 C 0.9786(5) 0.9677(2) 1.0161(4) 0.0568(18) Uani 1 1 d . . . H16A H 0.9774 0.9666 1.0824 0.068 Uiso 1 1 calc R . . C17 C 0.7559(5) 0.4076(4) 0.7169(5) 0.0611(18) Uani 1 1 d . . . C18 C 0.7795(5) 0.4027(3) 0.8168(5) 0.071(2) Uani 1 1 d . . . H18A H 0.7602 0.4452 0.8527 0.085 Uiso 1 1 calc R . . C19 C 0.8305(6) 0.3373(4) 0.8649(5) 0.085(2) Uani 1 1 d . . . H19A H 0.8485 0.3355 0.9329 0.102 Uiso 1 1 calc R . . C20 C 0.8556(6) 0.2725(4) 0.8100(7) 0.095(3) Uani 1 1 d . . . H20A H 0.8878 0.2270 0.8427 0.114 Uiso 1 1 calc R . . C21 C 0.8349(6) 0.2739(4) 0.7124(7) 0.093(2) Uani 1 1 d . . . H21A H 0.8532 0.2304 0.6777 0.112 Uiso 1 1 calc R . . C22 C 0.7849(6) 0.3425(4) 0.6632(6) 0.0638(18) Uani 1 1 d . . . C23 C 0.7615(6) 0.3493(4) 0.5613(6) 0.077(2) Uani 1 1 d . . . H23A H 0.7772 0.3067 0.5241 0.093 Uiso 1 1 calc R . . C24 C 0.7157(5) 0.4178(4) 0.5148(4) 0.0680(18) Uani 1 1 d . . . H24A H 0.7035 0.4225 0.4471 0.082 Uiso 1 1 calc R . . C25 C 0.6877(5) 0.4804(4) 0.5722(5) 0.0538(16) Uani 1 1 d . . . C26 C 0.6362(5) 0.5547(3) 0.5278(4) 0.0543(16) Uani 1 1 d . . . C27 C 0.6200(5) 0.5708(4) 0.4266(4) 0.0647(17) Uani 1 1 d . . . H27A H 0.6416 0.5338 0.3841 0.078 Uiso 1 1 calc R . . C28 C 0.5719(6) 0.6420(4) 0.3927(5) 0.073(2) Uani 1 1 d . . . H28A H 0.5614 0.6537 0.3265 0.088 Uiso 1 1 calc R . . C29 C 0.5380(6) 0.6978(4) 0.4563(5) 0.0598(18) Uani 1 1 d . . . C30 C 0.4857(6) 0.7706(4) 0.4245(5) 0.083(2) Uani 1 1 d . . . H30A H 0.4732 0.7843 0.3587 0.099 Uiso 1 1 calc R . . C31 C 0.4538(7) 0.8201(4) 0.4882(6) 0.090(2) Uani 1 1 d . . . H31A H 0.4159 0.8676 0.4664 0.108 Uiso 1 1 calc R . . C32 C 0.4768(6) 0.8015(4) 0.5888(5) 0.084(2) Uani 1 1 d . . . H32A H 0.4569 0.8375 0.6332 0.100 Uiso 1 1 calc R . . C33 C 0.5272(5) 0.7321(3) 0.6202(4) 0.0648(18) Uani 1 1 d . . . H33A H 0.5411 0.7196 0.6864 0.078 Uiso 1 1 calc R . . C34 C 0.5587(5) 0.6785(4) 0.5544(5) 0.0496(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0544(5) 0.0524(4) 0.0474(4) -0.0053(4) 0.0147(3) -0.0047(4) N1 0.048(3) 0.047(3) 0.058(4) -0.004(3) 0.012(3) 0.000(3) N2 0.041(3) 0.054(3) 0.049(3) 0.002(3) 0.010(3) -0.010(3) O1 0.057(3) 0.084(3) 0.083(3) -0.001(2) 0.033(3) 0.000(3) O2 0.074(3) 0.080(3) 0.058(3) -0.002(2) 0.032(2) -0.019(2) O3 0.069(3) 0.051(2) 0.050(2) -0.0070(19) 0.019(2) -0.017(2) O4 0.089(4) 0.093(3) 0.073(3) -0.027(2) 0.031(3) -0.027(3) C1 0.066(6) 0.055(5) 0.049(5) -0.030(4) 0.018(5) -0.019(4) C2 0.045(5) 0.040(3) 0.049(4) -0.003(3) 0.012(4) -0.001(3) C3 0.072(5) 0.051(3) 0.044(4) 0.005(3) 0.024(4) -0.006(4) C4 0.065(5) 0.046(4) 0.050(4) 0.009(3) 0.010(4) 0.010(3) C5 0.052(5) 0.069(4) 0.062(4) 0.001(4) 0.021(4) 0.003(4) C6 0.079(6) 0.065(4) 0.047(4) 0.007(3) 0.026(4) -0.017(4) C7 0.043(5) 0.051(4) 0.065(5) -0.013(3) 0.024(4) -0.012(4) C8 0.068(5) 0.068(5) 0.068(6) 0.007(4) 0.000(5) -0.013(4) C9 0.056(5) 0.057(4) 0.044(4) -0.003(4) 0.011(4) -0.006(4) C10 0.043(4) 0.049(4) 0.041(4) 0.001(3) 0.006(3) -0.004(3) C11 0.057(5) 0.070(4) 0.050(4) -0.008(4) 0.017(4) -0.008(4) C12 0.057(4) 0.045(4) 0.048(4) 0.001(3) 0.010(3) 0.001(3) C13 0.059(5) 0.054(4) 0.065(5) 0.006(3) 0.015(4) -0.010(3) C14 0.051(5) 0.056(4) 0.050(4) -0.001(4) 0.010(3) 0.010(3) C15 0.031(4) 0.053(4) 0.057(4) -0.006(3) 0.006(3) 0.008(3) C16 0.048(4) 0.048(4) 0.074(5) -0.019(4) 0.013(3) 0.001(4) C17 0.060(5) 0.051(5) 0.069(5) -0.009(4) 0.009(4) -0.005(3) C18 0.072(5) 0.053(5) 0.075(5) 0.004(4) -0.010(4) 0.012(3) C19 0.076(6) 0.073(5) 0.093(6) -0.005(5) -0.014(5) -0.003(4) C20 0.094(6) 0.054(5) 0.125(7) 0.011(6) -0.004(6) 0.003(4) C21 0.086(6) 0.066(6) 0.127(7) -0.002(6) 0.023(6) 0.012(4) C22 0.056(5) 0.056(5) 0.075(5) -0.006(4) 0.006(4) -0.004(4) C23 0.074(5) 0.060(5) 0.105(7) -0.030(4) 0.035(5) -0.007(4) C24 0.067(5) 0.066(4) 0.078(5) -0.011(4) 0.031(4) -0.010(4) C25 0.036(4) 0.061(4) 0.068(5) -0.014(4) 0.019(4) -0.011(3) C26 0.057(4) 0.058(4) 0.049(4) -0.011(4) 0.011(4) -0.012(4) C27 0.069(5) 0.085(5) 0.042(4) -0.020(4) 0.014(3) -0.030(4) C28 0.073(6) 0.094(5) 0.049(5) 0.014(5) 0.006(4) -0.028(5) C29 0.059(5) 0.068(5) 0.057(5) 0.014(4) 0.023(4) -0.006(4) C30 0.097(6) 0.079(6) 0.069(6) 0.025(5) 0.009(5) -0.009(5) C31 0.103(7) 0.072(5) 0.082(6) 0.031(5) -0.005(5) 0.003(5) C32 0.100(6) 0.063(5) 0.085(6) 0.004(4) 0.012(5) -0.001(4) C33 0.080(5) 0.048(4) 0.067(5) 0.017(4) 0.016(4) 0.015(4) C34 0.052(5) 0.052(4) 0.047(5) 0.006(4) 0.015(4) 0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 1.946(3) . ? Zn1 N1 2.068(4) . ? Zn1 N2 2.084(4) . ? Zn1 O2 2.165(4) . ? Zn1 O1 2.222(4) . ? Zn1 O4 2.890(4) . ? Zn1 Zn1 6.9835(12) 3_666 ? N1 C25 1.341(6) . ? N1 C17 1.374(6) . ? N2 C26 1.333(5) . ? N2 C34 1.362(5) . ? O1 C1 1.240(6) . ? O2 C1 1.256(6) . ? O3 C9 1.247(6) . ? O4 C9 1.231(6) . ? C1 C2 1.517(8) . ? C2 C4 1.354(6) . ? C2 C3 1.369(6) . ? C3 C5 1.373(6) . ? C4 C6 1.388(7) . ? C5 C7 1.370(6) . ? C6 C7 1.381(7) . ? C7 C8 1.498(8) . ? C8 C8 1.270(9) 3_567 ? C9 C10 1.513(7) . ? C10 C12 1.366(6) . ? C10 C11 1.384(6) . ? C11 C13 1.384(6) . ? C12 C14 1.378(6) . ? C13 C15 1.400(6) . ? C14 C15 1.384(6) . ? C15 C16 1.473(6) . ? C16 C16 1.312(8) 3_777 ? C17 C18 1.367(7) . ? C17 C22 1.412(7) . ? C18 C19 1.358(6) . ? C19 C20 1.402(7) . ? C20 C21 1.334(7) . ? C21 C22 1.405(7) . ? C22 C23 1.398(7) . ? C23 C24 1.375(7) . ? C24 C25 1.406(6) . ? C25 C26 1.467(6) . ? C26 C27 1.415(6) . ? C27 C28 1.365(7) . ? C28 C29 1.403(7) . ? C29 C34 1.381(7) . ? C29 C30 1.398(7) . ? C30 C31 1.326(7) . ? C31 C32 1.410(7) . ? C32 C33 1.339(6) . ? C33 C34 1.390(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 N1 127.36(17) . . ? O3 Zn1 N2 114.52(16) . . ? N1 Zn1 N2 79.6(2) . . ? O3 Zn1 O2 106.80(14) . . ? N1 Zn1 O2 124.61(15) . . ? N2 Zn1 O2 88.92(16) . . ? O3 Zn1 O1 100.59(15) . . ? N1 Zn1 O1 96.57(17) . . ? N2 Zn1 O1 138.60(16) . . ? O2 Zn1 O1 59.25(14) . . ? O3 Zn1 O4 49.15(13) . . ? N1 Zn1 O4 92.82(15) . . ? N2 Zn1 O4 75.65(13) . . ? O2 Zn1 O4 136.41(13) . . ? O1 Zn1 O4 145.61(14) . . ? O3 Zn1 Zn1 156.11(11) . 3_666 ? N1 Zn1 Zn1 57.66(14) . 3_666 ? N2 Zn1 Zn1 41.61(12) . 3_666 ? O2 Zn1 Zn1 78.16(9) . 3_666 ? O1 Zn1 Zn1 101.83(10) . 3_666 ? O4 Zn1 Zn1 111.09(8) . 3_666 ? C25 N1 C17 120.3(5) . . ? C25 N1 Zn1 113.3(4) . . ? C17 N1 Zn1 126.0(4) . . ? C26 N2 C34 119.8(5) . . ? C26 N2 Zn1 113.8(4) . . ? C34 N2 Zn1 126.4(4) . . ? C1 O1 Zn1 88.9(4) . . ? C1 O2 Zn1 91.1(4) . . ? C9 O3 Zn1 114.9(4) . . ? C9 O4 Zn1 69.5(4) . . ? O1 C1 O2 120.7(7) . . ? O1 C1 C2 120.5(6) . . ? O2 C1 C2 118.8(6) . . ? C4 C2 C3 119.2(6) . . ? C4 C2 C1 121.3(6) . . ? C3 C2 C1 119.5(6) . . ? C2 C3 C5 121.5(5) . . ? C2 C4 C6 120.0(5) . . ? C7 C5 C3 119.8(6) . . ? C7 C6 C4 120.6(5) . . ? C5 C7 C6 118.8(6) . . ? C5 C7 C8 118.3(6) . . ? C6 C7 C8 122.9(6) . . ? C8 C8 C7 128.3(9) 3_567 . ? O4 C9 O3 123.9(6) . . ? O4 C9 C10 118.0(6) . . ? O3 C9 C10 118.1(5) . . ? C12 C10 C11 118.3(5) . . ? C12 C10 C9 122.0(5) . . ? C11 C10 C9 119.7(5) . . ? C13 C11 C10 121.0(5) . . ? C10 C12 C14 120.9(5) . . ? C11 C13 C15 121.1(5) . . ? C12 C14 C15 122.4(5) . . ? C14 C15 C13 116.4(5) . . ? C14 C15 C16 120.7(5) . . ? C13 C15 C16 123.0(5) . . ? C16 C16 C15 127.7(7) 3_777 . ? C18 C17 N1 120.7(6) . . ? C18 C17 C22 118.6(6) . . ? N1 C17 C22 120.7(6) . . ? C19 C18 C17 121.7(6) . . ? C18 C19 C20 118.8(7) . . ? C21 C20 C19 122.3(7) . . ? C20 C21 C22 118.7(7) . . ? C23 C22 C21 122.5(7) . . ? C23 C22 C17 117.6(6) . . ? C21 C22 C17 120.0(7) . . ? C24 C23 C22 121.5(6) . . ? C23 C24 C25 118.3(6) . . ? N1 C25 C24 121.6(6) . . ? N1 C25 C26 116.9(6) . . ? C24 C25 C26 121.5(6) . . ? N2 C26 C27 121.1(5) . . ? N2 C26 C25 115.9(5) . . ? C27 C26 C25 123.0(6) . . ? C28 C27 C26 118.4(6) . . ? C27 C28 C29 121.1(6) . . ? C34 C29 C30 119.7(6) . . ? C34 C29 C28 117.3(6) . . ? C30 C29 C28 123.1(7) . . ? C31 C30 C29 120.0(7) . . ? C30 C31 C32 120.6(7) . . ? C33 C32 C31 120.0(6) . . ? C32 C33 C34 120.3(6) . . ? N2 C34 C29 122.3(6) . . ? N2 C34 C33 118.3(6) . . ? C29 C34 C33 119.4(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 O3 Zn1 N1 C25 -119.9(4) . . . . ? N2 Zn1 N1 C25 -6.9(4) . . . . ? O2 Zn1 N1 C25 74.5(4) . . . . ? O1 Zn1 N1 C25 131.4(4) . . . . ? O4 Zn1 N1 C25 -81.8(4) . . . . ? Zn1 Zn1 N1 C25 31.5(3) 3_666 . . . ? O3 Zn1 N1 C17 67.7(5) . . . . ? N2 Zn1 N1 C17 -179.3(5) . . . . ? O2 Zn1 N1 C17 -97.9(4) . . . . ? O1 Zn1 N1 C17 -41.0(5) . . . . ? O4 Zn1 N1 C17 105.9(4) . . . . ? Zn1 Zn1 N1 C17 -140.8(5) 3_666 . . . ? O3 Zn1 N2 C26 131.3(3) . . . . ? N1 Zn1 N2 C26 4.8(3) . . . . ? O2 Zn1 N2 C26 -120.7(4) . . . . ? O1 Zn1 N2 C26 -83.3(4) . . . . ? O4 Zn1 N2 C26 100.5(4) . . . . ? Zn1 Zn1 N2 C26 -47.4(3) 3_666 . . . ? O3 Zn1 N2 C34 -50.2(5) . . . . ? N1 Zn1 N2 C34 -176.7(4) . . . . ? O2 Zn1 N2 C34 57.8(4) . . . . ? O1 Zn1 N2 C34 95.2(5) . . . . ? O4 Zn1 N2 C34 -81.0(4) . . . . ? Zn1 Zn1 N2 C34 131.0(5) 3_666 . . . ? O3 Zn1 O1 C1 101.6(3) . . . . ? N1 Zn1 O1 C1 -128.4(3) . . . . ? N2 Zn1 O1 C1 -46.6(4) . . . . ? O2 Zn1 O1 C1 -1.7(3) . . . . ? O4 Zn1 O1 C1 126.8(3) . . . . ? Zn1 Zn1 O1 C1 -70.1(3) 3_666 . . . ? O3 Zn1 O2 C1 -90.8(3) . . . . ? N1 Zn1 O2 C1 77.3(3) . . . . ? N2 Zn1 O2 C1 153.8(3) . . . . ? O1 Zn1 O2 C1 1.7(3) . . . . ? O4 Zn1 O2 C1 -138.4(3) . . . . ? Zn1 Zn1 O2 C1 113.3(3) 3_666 . . . ? N1 Zn1 O3 C9 64.1(5) . . . . ? N2 Zn1 O3 C9 -31.5(4) . . . . ? O2 Zn1 O3 C9 -128.2(4) . . . . ? O1 Zn1 O3 C9 171.0(4) . . . . ? O4 Zn1 O3 C9 9.5(4) . . . . ? Zn1 Zn1 O3 C9 -29.4(6) 3_666 . . . ? O3 Zn1 O4 C9 -9.3(3) . . . . ? N1 Zn1 O4 C9 -148.8(4) . . . . ? N2 Zn1 O4 C9 132.7(4) . . . . ? O2 Zn1 O4 C9 60.0(4) . . . . ? O1 Zn1 O4 C9 -42.9(5) . . . . ? Zn1 Zn1 O4 C9 154.9(3) 3_666 . . . ? Zn1 O1 C1 O2 3.0(5) . . . . ? Zn1 O1 C1 C2 -174.3(4) . . . . ? Zn1 O2 C1 O1 -3.0(5) . . . . ? Zn1 O2 C1 C2 174.3(4) . . . . ? O1 C1 C2 C4 5.3(8) . . . . ? O2 C1 C2 C4 -172.1(4) . . . . ? O1 C1 C2 C3 -177.3(5) . . . . ? O2 C1 C2 C3 5.3(7) . . . . ? C4 C2 C3 C5 2.9(8) . . . . ? C1 C2 C3 C5 -174.5(5) . . . . ? C3 C2 C4 C6 -3.3(7) . . . . ? C1 C2 C4 C6 174.0(5) . . . . ? C2 C3 C5 C7 0.1(8) . . . . ? C2 C4 C6 C7 0.8(8) . . . . ? C3 C5 C7 C6 -2.7(8) . . . . ? C3 C5 C7 C8 174.9(5) . . . . ? C4 C6 C7 C5 2.3(8) . . . . ? C4 C6 C7 C8 -175.2(5) . . . . ? C5 C7 C8 C8 -175.6(8) . . . 3_567 ? C6 C7 C8 C8 2.0(12) . . . 3_567 ? Zn1 O4 C9 O3 13.3(5) . . . . ? Zn1 O4 C9 C10 -169.6(5) . . . . ? Zn1 O3 C9 O4 -20.6(8) . . . . ? Zn1 O3 C9 C10 162.3(3) . . . . ? O4 C9 C10 C12 -147.7(6) . . . . ? O3 C9 C10 C12 29.5(8) . . . . ? O4 C9 C10 C11 34.1(8) . . . . ? O3 C9 C10 C11 -148.7(5) . . . . ? C12 C10 C11 C13 0.9(8) . . . . ? C9 C10 C11 C13 179.2(5) . . . . ? C11 C10 C12 C14 -2.3(8) . . . . ? C9 C10 C12 C14 179.5(5) . . . . ? C10 C11 C13 C15 1.2(8) . . . . ? C10 C12 C14 C15 1.6(8) . . . . ? C12 C14 C15 C13 0.5(8) . . . . ? C12 C14 C15 C16 -179.4(5) . . . . ? C11 C13 C15 C14 -1.9(8) . . . . ? C11 C13 C15 C16 178.0(5) . . . . ? C14 C15 C16 C16 176.1(7) . . . 3_777 ? C13 C15 C16 C16 -3.9(11) . . . 3_777 ? C25 N1 C17 C18 177.5(5) . . . . ? Zn1 N1 C17 C18 -10.6(8) . . . . ? C25 N1 C17 C22 -1.6(8) . . . . ? Zn1 N1 C17 C22 170.2(4) . . . . ? N1 C17 C18 C19 -178.7(5) . . . . ? C22 C17 C18 C19 0.4(9) . . . . ? C17 C18 C19 C20 -2.1(10) . . . . ? C18 C19 C20 C21 2.3(11) . . . . ? C19 C20 C21 C22 -0.8(12) . . . . ? C20 C21 C22 C23 179.3(7) . . . . ? C20 C21 C22 C17 -1.0(10) . . . . ? C18 C17 C22 C23 -179.1(6) . . . . ? N1 C17 C22 C23 0.0(9) . . . . ? C18 C17 C22 C21 1.1(9) . . . . ? N1 C17 C22 C21 -179.7(6) . . . . ? C21 C22 C23 C24 -178.2(6) . . . . ? C17 C22 C23 C24 2.1(9) . . . . ? C22 C23 C24 C25 -2.6(9) . . . . ? C17 N1 C25 C24 1.1(8) . . . . ? Zn1 N1 C25 C24 -171.7(4) . . . . ? C17 N1 C25 C26 -179.2(5) . . . . ? Zn1 N1 C25 C26 8.0(6) . . . . ? C23 C24 C25 N1 1.0(9) . . . . ? C23 C24 C25 C26 -178.7(5) . . . . ? C34 N2 C26 C27 0.0(7) . . . . ? Zn1 N2 C26 C27 178.6(4) . . . . ? C34 N2 C26 C25 179.3(5) . . . . ? Zn1 N2 C26 C25 -2.1(6) . . . . ? N1 C25 C26 N2 -4.0(7) . . . . ? C24 C25 C26 N2 175.7(5) . . . . ? N1 C25 C26 C27 175.3(5) . . . . ? C24 C25 C26 C27 -5.0(8) . . . . ? N2 C26 C27 C28 -0.4(8) . . . . ? C25 C26 C27 C28 -179.6(5) . . . . ? C26 C27 C28 C29 -0.6(9) . . . . ? C27 C28 C29 C34 1.9(9) . . . . ? C27 C28 C29 C30 -178.4(6) . . . . ? C34 C29 C30 C31 -1.4(10) . . . . ? C28 C29 C30 C31 178.9(7) . . . . ? C29 C30 C31 C32 2.6(11) . . . . ? C30 C31 C32 C33 -2.4(11) . . . . ? C31 C32 C33 C34 0.9(9) . . . . ? C26 N2 C34 C29 1.4(8) . . . . ? Zn1 N2 C34 C29 -177.0(4) . . . . ? C26 N2 C34 C33 179.4(5) . . . . ? Zn1 N2 C34 C33 1.0(7) . . . . ? C30 C29 C34 N2 178.0(5) . . . . ? C28 C29 C34 N2 -2.3(9) . . . . ? C30 C29 C34 C33 0.0(9) . . . . ? C28 C29 C34 C33 179.7(5) . . . . ? C32 C33 C34 N2 -177.9(5) . . . . ? C32 C33 C34 C29 0.2(9) . . . . ? 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 C14 H14A O4 0.93 2.39 3.288(7) 161.6 4_576 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.317 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.058 # Attachment '4b.cif' ## Crystallographic Data of Complex 4 data_4b _database_code_depnum_ccdc_archive 'CCDC 654227' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H18 N2 O4 Zn' _chemical_formula_weight 511.81 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 tetragonal _symmetry_space_group_name_H-M P4/ncc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, -z+1/2' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'y+1/2, x+1/2, -z+1/2' 'y, -x+1/2, z' '-y+1/2, x, z' '-y, -x, -z+1/2' '-x, -y, -z' '-x-1/2, y, z-1/2' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-y-1/2, -x-1/2, z-1/2' '-y, x-1/2, -z' 'y-1/2, -x, -z' 'y, x, z-1/2' _cell_length_a 16.1919(6) _cell_length_b 16.1919(5) _cell_length_c 19.7472(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5177.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 34295 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 25.028 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2096 _exptl_absorpt_coefficient_mu 0.983 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8429 _exptl_absorpt_correction_T_max 0.9081 _exptl_absorpt_process_details '(Blessing, 1995, 1997)' _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 'NONIUS KappaCCD Diffractometer' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8317 _diffrn_reflns_av_R_equivalents 0.1968 _diffrn_reflns_av_sigmaI/netI 0.1866 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2286 _reflns_number_gt 850 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD (Nonius B. V., 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1762P)^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 2286 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2227 _refine_ls_R_factor_gt 0.0803 _refine_ls_wR_factor_ref 0.3243 _refine_ls_wR_factor_gt 0.2740 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _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 0.55601(7) 0.05601(7) 0.2500 0.0446(7) Uani 1 2 d S . . N1 N 0.4484(5) 0.0253(5) 0.1974(4) 0.046(2) Uani 1 1 d . . . O1 O 0.5223(4) 0.1609(4) 0.2891(4) 0.0501(19) Uani 1 1 d . . . O2 O 0.6178(4) 0.1281(4) 0.3635(4) 0.056(2) Uani 1 1 d . . . C1 C 0.5633(6) 0.1760(6) 0.3429(5) 0.040(3) Uani 1 1 d . . . C2 C 0.5407(6) 0.2519(6) 0.3798(5) 0.038(2) Uani 1 1 d . . . C3 C 0.4782(7) 0.3019(6) 0.3563(5) 0.051(3) Uani 1 1 d . . . H3A H 0.4499 0.2862 0.3174 0.062 Uiso 1 1 calc R . . C4 C 0.5792(7) 0.2737(6) 0.4360(5) 0.055(3) Uani 1 1 d . . . H4A H 0.6199 0.2391 0.4534 0.065 Uiso 1 1 calc R . . C5 C 0.4558(6) 0.3744(7) 0.3883(5) 0.054(3) Uani 1 1 d . . . H5A H 0.4122 0.4060 0.3719 0.065 Uiso 1 1 calc R . . C6 C 0.5607(6) 0.3480(7) 0.4707(6) 0.057(3) Uani 1 1 d . . . H6A H 0.5890 0.3622 0.5100 0.068 Uiso 1 1 calc R . . C7 C 0.4994(7) 0.3993(6) 0.4451(6) 0.054(3) Uani 1 1 d . . . C8 C 0.4785(7) 0.4795(7) 0.4773(5) 0.065(3) Uani 1 1 d . . . H8A H 0.4290 0.5036 0.4638 0.078 Uiso 1 1 calc R . . C9 C 0.4107(7) 0.0641(6) 0.1467(6) 0.057(3) Uani 1 1 d . . . H9A H 0.4342 0.1117 0.1288 0.068 Uiso 1 1 calc R . . C10 C 0.3373(7) 0.0350(7) 0.1200(6) 0.063(3) Uani 1 1 d . . . H10A H 0.3119 0.0644 0.0853 0.076 Uiso 1 1 calc R . . C11 C 0.3014(7) -0.0351(7) 0.1432(5) 0.057(3) Uani 1 1 d . . . H11A H 0.2521 -0.0541 0.1247 0.068 Uiso 1 1 calc R . . C12 C 0.3399(6) -0.0777(6) 0.1950(5) 0.050(3) Uani 1 1 d . . . C13 C 0.4137(6) -0.0460(6) 0.2215(6) 0.048(3) Uani 1 1 d . . . C14 C 0.3080(7) -0.1520(6) 0.2239(5) 0.056(3) Uani 1 1 d . . . H14A H 0.2591 -0.1740 0.2070 0.067 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 0.0344(8) 0.0344(8) 0.0652(13) -0.0083(6) 0.0083(6) -0.0039(8) N1 0.037(5) 0.036(5) 0.063(6) -0.005(5) 0.010(5) -0.007(4) O1 0.053(5) 0.036(4) 0.061(5) -0.008(4) 0.009(4) 0.001(4) O2 0.061(5) 0.043(5) 0.065(5) -0.003(4) 0.008(4) 0.006(4) C1 0.042(7) 0.036(6) 0.041(7) 0.005(5) 0.008(6) -0.008(6) C2 0.040(6) 0.032(6) 0.042(6) -0.010(5) 0.001(5) 0.001(5) C3 0.063(8) 0.043(7) 0.048(7) -0.003(6) 0.005(6) -0.011(6) C4 0.065(8) 0.035(7) 0.064(8) 0.004(6) -0.004(7) 0.015(5) C5 0.057(7) 0.049(7) 0.056(8) -0.004(6) -0.008(6) -0.001(6) C6 0.056(7) 0.057(8) 0.057(7) -0.003(6) -0.013(6) 0.001(6) C7 0.064(8) 0.031(6) 0.067(8) 0.005(6) 0.018(7) 0.005(6) C8 0.062(8) 0.065(9) 0.067(9) -0.007(7) 0.015(7) 0.000(7) C9 0.056(8) 0.044(7) 0.071(8) 0.005(6) -0.001(7) 0.006(6) C10 0.058(8) 0.058(8) 0.074(9) 0.011(7) -0.025(7) 0.007(6) C11 0.043(7) 0.065(8) 0.063(8) 0.009(7) -0.015(6) -0.004(6) C12 0.038(7) 0.042(7) 0.069(8) -0.011(6) 0.016(6) -0.013(5) C13 0.034(6) 0.043(7) 0.069(7) 0.000(5) 0.012(5) -0.001(5) C14 0.047(7) 0.046(7) 0.074(9) -0.013(6) 0.001(5) -0.011(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.944(6) 5_545 ? Zn1 O1 1.944(6) . ? Zn1 N1 2.088(8) . ? Zn1 N1 2.088(8) 5_545 ? N1 C9 1.330(12) . ? N1 C13 1.370(11) . ? O1 C1 1.277(11) . ? O2 C1 1.244(11) . ? C1 C2 1.475(13) . ? C2 C4 1.322(12) . ? C2 C3 1.375(13) . ? C3 C5 1.382(13) . ? C4 C6 1.417(13) . ? C5 C7 1.386(13) . ? C6 C7 1.389(14) . ? C7 C8 1.486(15) . ? C8 C8 1.32(2) 9_666 ? C9 C10 1.383(14) . ? C10 C11 1.356(14) . ? C11 C12 1.383(13) . ? C12 C13 1.402(14) . ? C12 C14 1.428(13) . ? C13 C13 1.45(2) 5_545 ? C14 C14 1.379(19) 5_545 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O1 130.4(4) 5_545 . ? O1 Zn1 N1 117.7(3) 5_545 . ? O1 Zn1 N1 99.8(3) . . ? O1 Zn1 N1 99.8(3) 5_545 5_545 ? O1 Zn1 N1 117.7(3) . 5_545 ? N1 Zn1 N1 81.4(5) . 5_545 ? C9 N1 C13 118.1(9) . . ? C9 N1 Zn1 130.2(7) . . ? C13 N1 Zn1 111.7(7) . . ? C1 O1 Zn1 110.6(6) . . ? O2 C1 O1 121.5(9) . . ? O2 C1 C2 122.3(10) . . ? O1 C1 C2 116.2(9) . . ? C4 C2 C3 118.2(9) . . ? C4 C2 C1 121.4(10) . . ? C3 C2 C1 120.4(9) . . ? C2 C3 C5 122.6(10) . . ? C2 C4 C6 122.2(10) . . ? C3 C5 C7 118.9(10) . . ? C7 C6 C4 118.9(10) . . ? C5 C7 C6 119.0(10) . . ? C5 C7 C8 119.0(10) . . ? C6 C7 C8 122.0(11) . . ? C8 C8 C7 127.7(15) 9_666 . ? N1 C9 C10 121.4(10) . . ? C11 C10 C9 121.7(10) . . ? C10 C11 C12 118.3(10) . . ? C11 C12 C13 118.6(9) . . ? C11 C12 C14 123.5(10) . . ? C13 C12 C14 117.9(11) . . ? N1 C13 C12 121.9(10) . . ? N1 C13 C13 117.6(6) . 5_545 ? C12 C13 C13 120.4(6) . 5_545 ? C14 C14 C12 121.6(6) 5_545 . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.349 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.120