# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Liya Wang' _publ_contact_author_address ; Luoyang 471022 ; _publ_contact_author_email wlya@lynu.edu.cn loop_ _publ_author_name 'Kai Jiang' 'Xiaoyuan Sun' 'Lufang Ma' 'Liya Wang' # Attachment '- 1.cif' data_b _database_code_depnum_ccdc_archive 'CCDC 762921' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 N4 O4 Zn' _chemical_formula_weight 419.73 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 8.1512(7) _cell_length_b 15.0605(13) _cell_length_c 14.8508(12) _cell_angle_alpha 90.00 _cell_angle_beta 93.7260(10) _cell_angle_gamma 90.00 _cell_volume 1819.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6014 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 28.04 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 1.382 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6433 _exptl_absorpt_correction_T_max 0.7990 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15888 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4160 _reflns_number_gt 3501 _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^)+(0.0365P)^2^+0.5776P] 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 4160 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0714 _refine_ls_wR_factor_gt 0.0676 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.004 _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 0.03564(2) 1.194098(13) 0.323595(13) 0.02761(7) Uani 1 1 d . . . O1 O -0.09871(19) 1.15801(9) 0.21927(9) 0.0438(3) Uani 1 1 d . . . O2 O -0.23446(19) 1.03929(10) 0.26558(9) 0.0491(4) Uani 1 1 d . . . O3 O -0.05489(17) 1.22900(9) -0.08864(9) 0.0393(3) Uani 1 1 d . . . O4 O -0.08859(19) 1.12812(9) -0.19719(9) 0.0454(3) Uani 1 1 d . . . N1 N 0.11241(18) 1.08725(9) 0.39769(10) 0.0315(3) Uani 1 1 d . . . N2 N 0.18822(18) 0.95167(9) 0.43376(10) 0.0307(3) Uani 1 1 d . . . N3 N 0.5447(2) 0.81280(11) 0.26968(12) 0.0401(4) Uani 1 1 d . . . N4 N 0.74485(18) 0.73724(10) 0.21452(11) 0.0361(3) Uani 1 1 d . . . C1 C -0.2016(2) 1.05891(11) 0.10825(11) 0.0284(4) Uani 1 1 d . . . C2 C -0.1439(2) 1.11395(11) 0.04243(11) 0.0283(4) Uani 1 1 d . . . H2 H -0.0943 1.1676 0.0591 0.034 Uiso 1 1 calc R . . C3 C -0.1591(2) 1.08990(11) -0.04805(11) 0.0286(4) Uani 1 1 d . . . C4 C -0.2298(2) 1.00823(12) -0.07197(12) 0.0348(4) Uani 1 1 d . . . H4 H -0.2381 0.9912 -0.1323 0.042 Uiso 1 1 calc R . . C5 C -0.2881(2) 0.95167(12) -0.00705(13) 0.0363(4) Uani 1 1 d . . . C6 C -0.2749(2) 0.97851(12) 0.08236(12) 0.0339(4) Uani 1 1 d . . . H6 H -0.3159 0.9420 0.1261 0.041 Uiso 1 1 calc R . . C7 C -0.1785(2) 1.08485(12) 0.20611(12) 0.0327(4) Uani 1 1 d . . . C8 C -0.0968(2) 1.15117(12) -0.11779(12) 0.0307(4) Uani 1 1 d . . . C9 C -0.3608(3) 0.86249(15) -0.03341(17) 0.0589(6) Uani 1 1 d . . . H9A H -0.2751 0.8187 -0.0321 0.088 Uiso 1 1 calc R . . H9B H -0.4128 0.8660 -0.0932 0.088 Uiso 1 1 calc R . . H9C H -0.4407 0.8461 0.0083 0.088 Uiso 1 1 calc R . . C10 C 0.1247(2) 1.00497(12) 0.36840(12) 0.0306(4) Uani 1 1 d . . . H10 H 0.0934 0.9865 0.3100 0.037 Uiso 1 1 calc R . . C11 C 0.2181(2) 1.00241(14) 0.50995(13) 0.0385(4) Uani 1 1 d . . . H11 H 0.2614 0.9832 0.5661 0.046 Uiso 1 1 calc R . . C12 C 0.1716(2) 1.08613(13) 0.48671(13) 0.0376(4) Uani 1 1 d . . . H12 H 0.1785 1.1351 0.5249 0.045 Uiso 1 1 calc R . . C13 C 0.2211(3) 0.85636(12) 0.42454(15) 0.0416(5) Uani 1 1 d . . . H13A H 0.1518 0.8328 0.3746 0.050 Uiso 1 1 calc R . . H13B H 0.1927 0.8260 0.4790 0.050 Uiso 1 1 calc R . . C14 C 0.3989(3) 0.83771(17) 0.40843(16) 0.0541(6) Uani 1 1 d . . . H14A H 0.4153 0.7740 0.4069 0.065 Uiso 1 1 calc R . . H14B H 0.4677 0.8611 0.4587 0.065 Uiso 1 1 calc R . . C15 C 0.4545(3) 0.87816(15) 0.32039(16) 0.0500(5) Uani 1 1 d . . . H15A H 0.3591 0.8985 0.2836 0.060 Uiso 1 1 calc R . . H15B H 0.5245 0.9291 0.3344 0.060 Uiso 1 1 calc R . . C16 C 0.7067(2) 0.80912(12) 0.25962(13) 0.0351(4) Uani 1 1 d . . . H16 H 0.7821 0.8515 0.2815 0.042 Uiso 1 1 calc R . . C17 C 0.4749(3) 0.73933(16) 0.22877(17) 0.0529(6) Uani 1 1 d . . . H17 H 0.3640 0.7243 0.2249 0.063 Uiso 1 1 calc R . . C18 C 0.5982(3) 0.69326(14) 0.19532(17) 0.0492(5) Uani 1 1 d . . . H18 H 0.5866 0.6399 0.1640 0.059 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 0.03162(12) 0.02606(11) 0.02573(11) -0.00168(8) 0.00632(8) 0.00044(8) O1 0.0627(9) 0.0386(7) 0.0293(7) -0.0033(6) -0.0036(6) -0.0118(7) O2 0.0637(10) 0.0547(9) 0.0293(7) 0.0084(6) 0.0055(6) -0.0116(7) O3 0.0584(9) 0.0286(6) 0.0322(7) 0.0011(5) 0.0136(6) -0.0100(6) O4 0.0676(10) 0.0428(8) 0.0264(7) -0.0014(6) 0.0081(6) -0.0065(7) N1 0.0376(8) 0.0274(7) 0.0301(8) 0.0005(6) 0.0073(6) 0.0031(6) N2 0.0321(8) 0.0277(7) 0.0333(8) 0.0029(6) 0.0089(6) 0.0042(6) N3 0.0334(9) 0.0398(9) 0.0481(10) 0.0009(7) 0.0101(7) 0.0072(7) N4 0.0301(8) 0.0361(8) 0.0429(9) -0.0023(7) 0.0091(7) 0.0000(6) C1 0.0304(9) 0.0264(8) 0.0284(9) 0.0015(7) 0.0011(7) -0.0006(7) C2 0.0326(9) 0.0229(8) 0.0294(9) -0.0010(7) 0.0019(7) -0.0037(6) C3 0.0322(9) 0.0247(8) 0.0290(9) 0.0017(7) 0.0031(7) -0.0021(7) C4 0.0446(11) 0.0303(9) 0.0292(9) -0.0040(7) -0.0011(8) -0.0042(8) C5 0.0404(10) 0.0274(9) 0.0404(10) 0.0001(8) -0.0031(8) -0.0080(8) C6 0.0374(10) 0.0296(9) 0.0346(10) 0.0078(7) 0.0014(8) -0.0076(7) C7 0.0361(9) 0.0329(9) 0.0289(9) 0.0013(7) 0.0000(7) 0.0013(7) C8 0.0333(9) 0.0301(9) 0.0288(9) 0.0020(7) 0.0034(7) 0.0002(7) C9 0.0798(17) 0.0377(12) 0.0578(14) -0.0025(10) -0.0056(12) -0.0255(11) C10 0.0339(9) 0.0298(9) 0.0286(9) 0.0003(7) 0.0060(7) 0.0026(7) C11 0.0407(10) 0.0447(11) 0.0299(9) 0.0035(8) 0.0012(8) 0.0053(8) C12 0.0443(11) 0.0373(10) 0.0314(10) -0.0058(8) 0.0040(8) 0.0007(8) C13 0.0503(12) 0.0268(10) 0.0492(12) 0.0070(8) 0.0148(9) 0.0070(8) C14 0.0573(14) 0.0558(13) 0.0506(13) 0.0148(11) 0.0141(11) 0.0296(11) C15 0.0486(12) 0.0452(12) 0.0580(14) 0.0044(10) 0.0182(10) 0.0184(10) C16 0.0325(9) 0.0345(10) 0.0390(10) 0.0009(8) 0.0068(8) -0.0008(7) C17 0.0310(11) 0.0563(14) 0.0719(16) -0.0062(12) 0.0078(10) -0.0077(9) C18 0.0394(11) 0.0445(12) 0.0641(14) -0.0145(10) 0.0079(10) -0.0069(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.9169(13) . ? Zn1 O3 1.9261(12) 4_586 ? Zn1 N4 2.0188(15) 2_655 ? Zn1 N1 2.0254(15) . ? O1 C7 1.288(2) . ? O2 C7 1.229(2) . ? O3 C8 1.288(2) . ? O3 Zn1 1.9261(12) 4_585 ? O4 C8 1.235(2) . ? N1 C10 1.319(2) . ? N1 C12 1.378(2) . ? N2 C10 1.338(2) . ? N2 C11 1.374(2) . ? N2 C13 1.468(2) . ? N3 C16 1.339(2) . ? N3 C17 1.368(3) . ? N3 C15 1.466(2) . ? N4 C16 1.321(2) . ? N4 C18 1.380(3) . ? N4 Zn1 2.0188(15) 2_645 ? C1 C2 1.387(2) . ? C1 C6 1.393(2) . ? C1 C7 1.505(2) . ? C2 C3 1.389(2) . ? C2 H2 0.9300 . ? C3 C4 1.394(2) . ? C3 C8 1.500(2) . ? C4 C5 1.393(3) . ? C4 H4 0.9300 . ? C5 C6 1.385(3) . ? C5 C9 1.509(3) . ? C6 H6 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10 0.9300 . ? C11 C12 1.355(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.511(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.537(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16 0.9300 . ? C17 C18 1.343(3) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O3 119.57(7) . 4_586 ? O1 Zn1 N4 109.56(6) . 2_655 ? O3 Zn1 N4 112.44(6) 4_586 2_655 ? O1 Zn1 N1 110.73(6) . . ? O3 Zn1 N1 103.21(6) 4_586 . ? N4 Zn1 N1 99.20(6) 2_655 . ? C7 O1 Zn1 128.43(12) . . ? C8 O3 Zn1 115.13(11) . 4_585 ? C10 N1 C12 105.99(15) . . ? C10 N1 Zn1 126.49(12) . . ? C12 N1 Zn1 127.42(12) . . ? C10 N2 C11 107.66(15) . . ? C10 N2 C13 125.69(16) . . ? C11 N2 C13 126.65(16) . . ? C16 N3 C17 107.57(16) . . ? C16 N3 C15 128.02(18) . . ? C17 N3 C15 124.26(18) . . ? C16 N4 C18 105.59(16) . . ? C16 N4 Zn1 130.41(13) . 2_645 ? C18 N4 Zn1 124.00(14) . 2_645 ? C2 C1 C6 118.94(16) . . ? C2 C1 C7 119.91(15) . . ? C6 C1 C7 121.10(16) . . ? C1 C2 C3 120.84(15) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C2 C3 C4 119.07(16) . . ? C2 C3 C8 119.63(15) . . ? C4 C3 C8 121.30(16) . . ? C5 C4 C3 121.12(17) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C6 C5 C4 118.44(16) . . ? C6 C5 C9 120.86(18) . . ? C4 C5 C9 120.69(18) . . ? C5 C6 C1 121.55(16) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 119.2 . . ? O2 C7 O1 125.16(17) . . ? O2 C7 C1 121.34(17) . . ? O1 C7 C1 113.50(15) . . ? O4 C8 O3 123.16(16) . . ? O4 C8 C3 121.87(16) . . ? O3 C8 C3 114.96(15) . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 N2 111.02(16) . . ? N1 C10 H10 124.5 . . ? N2 C10 H10 124.5 . . ? C12 C11 N2 106.03(16) . . ? C12 C11 H11 127.0 . . ? N2 C11 H11 127.0 . . ? C11 C12 N1 109.30(17) . . ? C11 C12 H12 125.3 . . ? N1 C12 H12 125.3 . . ? N2 C13 C14 112.28(18) . . ? N2 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? N2 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.9 . . ? C13 C14 C15 113.59(18) . . ? C13 C14 H14A 108.8 . . ? C15 C14 H14A 108.8 . . ? C13 C14 H14B 108.8 . . ? C15 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? N3 C15 C14 110.88(17) . . ? N3 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? N3 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? N4 C16 N3 110.90(17) . . ? N4 C16 H16 124.5 . . ? N3 C16 H16 124.5 . . ? C18 C17 N3 106.37(18) . . ? C18 C17 H17 126.8 . . ? N3 C17 H17 126.8 . . ? C17 C18 N4 109.56(19) . . ? C17 C18 H18 125.2 . . ? N4 C18 H18 125.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Zn1 O1 C7 -98.29(17) 4_586 . . . ? N4 Zn1 O1 C7 129.83(16) 2_655 . . . ? N1 Zn1 O1 C7 21.42(18) . . . . ? O1 Zn1 N1 C10 23.14(16) . . . . ? O3 Zn1 N1 C10 152.25(15) 4_586 . . . ? N4 Zn1 N1 C10 -91.95(15) 2_655 . . . ? O1 Zn1 N1 C12 -161.18(15) . . . . ? O3 Zn1 N1 C12 -32.06(16) 4_586 . . . ? N4 Zn1 N1 C12 83.74(16) 2_655 . . . ? C6 C1 C2 C3 0.3(3) . . . . ? C7 C1 C2 C3 177.90(16) . . . . ? C1 C2 C3 C4 -1.6(3) . . . . ? C1 C2 C3 C8 179.47(16) . . . . ? C2 C3 C4 C5 1.4(3) . . . . ? C8 C3 C4 C5 -179.73(17) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? C3 C4 C5 C9 -178.6(2) . . . . ? C4 C5 C6 C1 -1.6(3) . . . . ? C9 C5 C6 C1 177.16(19) . . . . ? C2 C1 C6 C5 1.4(3) . . . . ? C7 C1 C6 C5 -176.20(17) . . . . ? Zn1 O1 C7 O2 28.8(3) . . . . ? Zn1 O1 C7 C1 -152.17(13) . . . . ? C2 C1 C7 O2 176.90(17) . . . . ? C6 C1 C7 O2 -5.5(3) . . . . ? C2 C1 C7 O1 -2.2(2) . . . . ? C6 C1 C7 O1 175.37(16) . . . . ? Zn1 O3 C8 O4 -3.7(2) 4_585 . . . ? Zn1 O3 C8 C3 176.98(11) 4_585 . . . ? C2 C3 C8 O4 170.68(18) . . . . ? C4 C3 C8 O4 -8.2(3) . . . . ? C2 C3 C8 O3 -10.0(2) . . . . ? C4 C3 C8 O3 171.13(17) . . . . ? C12 N1 C10 N2 0.1(2) . . . . ? Zn1 N1 C10 N2 176.49(11) . . . . ? C11 N2 C10 N1 0.3(2) . . . . ? C13 N2 C10 N1 -179.15(16) . . . . ? C10 N2 C11 C12 -0.5(2) . . . . ? C13 N2 C11 C12 178.94(17) . . . . ? N2 C11 C12 N1 0.5(2) . . . . ? C10 N1 C12 C11 -0.3(2) . . . . ? Zn1 N1 C12 C11 -176.74(13) . . . . ? C10 N2 C13 C14 98.1(2) . . . . ? C11 N2 C13 C14 -81.2(2) . . . . ? N2 C13 C14 C15 -62.3(3) . . . . ? C16 N3 C15 C14 -106.3(2) . . . . ? C17 N3 C15 C14 68.7(3) . . . . ? C13 C14 C15 N3 -132.8(2) . . . . ? C18 N4 C16 N3 -0.1(2) . . . . ? Zn1 N4 C16 N3 179.28(13) 2_645 . . . ? C17 N3 C16 N4 0.0(2) . . . . ? C15 N3 C16 N4 175.59(18) . . . . ? C16 N3 C17 C18 0.2(3) . . . . ? C15 N3 C17 C18 -175.7(2) . . . . ? N3 C17 C18 N4 -0.2(3) . . . . ? C16 N4 C18 C17 0.2(3) . . . . ? Zn1 N4 C18 C17 -179.23(16) 2_645 . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.294 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.049 # Attachment '- 3.cif' data_b_3 _database_code_depnum_ccdc_archive 'CCDC 762922' #TrackingRef '- 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 N4 O4 Zn' _chemical_formula_weight 447.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.4664(10) _cell_length_b 14.5654(15) _cell_length_c 15.1276(16) _cell_angle_alpha 90.00 _cell_angle_beta 102.2470(10) _cell_angle_gamma 90.00 _cell_volume 2038.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3249 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 24.06 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 1.239 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7001 _exptl_absorpt_correction_T_max 0.8656 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15326 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3794 _reflns_number_gt 2900 _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^)+(0.0376P)^2^+0.4088P] 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 3794 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0804 _refine_ls_wR_factor_gt 0.0724 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 0.76009(3) -0.161506(19) 0.45516(2) 0.03749(11) Uani 1 1 d . . . N1 N 0.7731(2) -0.03739(15) 0.40042(15) 0.0460(6) Uani 1 1 d . . . N2 N 0.7319(2) 0.10470(15) 0.35422(15) 0.0460(5) Uani 1 1 d . . . N3 N 0.7250(2) 0.59276(15) 0.21445(15) 0.0465(6) Uani 1 1 d . . . N4 N 0.7623(2) 0.64853(13) 0.08702(15) 0.0401(5) Uani 1 1 d . . . O1 O 0.59224(16) -0.23488(12) 0.40163(12) 0.0456(5) Uani 1 1 d . . . O2 O 0.45021(18) -0.12544(12) 0.43801(13) 0.0509(5) Uani 1 1 d . . . O3 O -0.1013(2) -0.34998(15) 0.47841(18) 0.0780(7) Uani 1 1 d . . . O4 O -0.06107(17) -0.21047(13) 0.43265(13) 0.0518(5) Uani 1 1 d . . . C1 C 0.3588(2) -0.27788(16) 0.41669(16) 0.0326(5) Uani 1 1 d . . . C2 C 0.2216(2) -0.25368(17) 0.42849(16) 0.0341(5) Uani 1 1 d . . . H2 H 0.1981 -0.1921 0.4328 0.041 Uiso 1 1 calc R . . C3 C 0.1201(2) -0.32067(16) 0.43385(16) 0.0354(6) Uani 1 1 d . . . C4 C 0.1548(3) -0.41239(18) 0.42720(18) 0.0448(7) Uani 1 1 d . . . H4 H 0.0875 -0.4572 0.4331 0.054 Uiso 1 1 calc R . . C5 C 0.2888(3) -0.43842(17) 0.41184(19) 0.0462(7) Uani 1 1 d . . . C6 C 0.3896(3) -0.36999(17) 0.40763(18) 0.0427(6) Uani 1 1 d . . . H6 H 0.4803 -0.3865 0.3985 0.051 Uiso 1 1 calc R . . C7 C 0.4726(2) -0.20561(18) 0.41844(16) 0.0366(6) Uani 1 1 d . . . C8 C -0.0258(3) -0.2940(2) 0.45099(18) 0.0427(6) Uani 1 1 d . . . C9 C 0.3239(3) -0.53855(19) 0.4007(2) 0.0737(10) Uani 1 1 d . . . H9A H 0.2756 -0.5756 0.4377 0.111 Uiso 1 1 calc R . . H9B H 0.4264 -0.5476 0.4189 0.111 Uiso 1 1 calc R . . H9C H 0.2920 -0.5560 0.3385 0.111 Uiso 1 1 calc R . . C10 C 0.8765(3) -0.0114(2) 0.3544(2) 0.0712(10) Uani 1 1 d . . . H10 H 0.9521 -0.0481 0.3445 0.085 Uiso 1 1 calc R . . C11 C 0.8510(4) 0.0761(2) 0.3256(2) 0.0743(10) Uani 1 1 d . . . H11 H 0.9049 0.1102 0.2925 0.089 Uiso 1 1 calc R . . C12 C 0.6892(3) 0.03476(19) 0.39801(18) 0.0481(7) Uani 1 1 d . . . H12 H 0.6087 0.0365 0.4241 0.058 Uiso 1 1 calc R . . C13 C 0.6578(3) 0.19351(19) 0.3374(2) 0.0520(7) Uani 1 1 d . . . H13A H 0.6123 0.2076 0.3875 0.062 Uiso 1 1 calc R . . H13B H 0.5822 0.1890 0.2831 0.062 Uiso 1 1 calc R . . C14 C 0.7583(3) 0.27062(18) 0.32619(19) 0.0489(7) Uani 1 1 d . . . H14A H 0.7940 0.2611 0.2713 0.059 Uiso 1 1 calc R . . H14B H 0.8405 0.2708 0.3769 0.059 Uiso 1 1 calc R . . C15 C 0.6813(3) 0.36271(19) 0.3212(2) 0.0548(8) Uani 1 1 d . . . H15A H 0.5862 0.3568 0.2822 0.066 Uiso 1 1 calc R . . H15B H 0.6685 0.3792 0.3811 0.066 Uiso 1 1 calc R . . C16 C 0.7627(3) 0.43854(19) 0.2856(2) 0.0585(8) Uani 1 1 d . . . H16A H 0.7780 0.4215 0.2264 0.070 Uiso 1 1 calc R . . H16B H 0.8566 0.4460 0.3256 0.070 Uiso 1 1 calc R . . C17 C 0.6816(3) 0.5289(2) 0.2785(2) 0.0601(8) Uani 1 1 d . . . H17A H 0.5788 0.5169 0.2597 0.072 Uiso 1 1 calc R . . H17B H 0.6984 0.5575 0.3378 0.072 Uiso 1 1 calc R . . C18 C 0.7202(3) 0.57707(18) 0.12722(18) 0.0433(6) Uani 1 1 d . . . H18 H 0.6905 0.5219 0.0982 0.052 Uiso 1 1 calc R . . C19 C 0.7949(3) 0.71397(19) 0.1525(2) 0.0541(8) Uani 1 1 d . . . H19 H 0.8278 0.7728 0.1440 0.065 Uiso 1 1 calc R . . C20 C 0.7725(3) 0.68072(19) 0.2311(2) 0.0580(8) Uani 1 1 d . . . H20 H 0.7866 0.7116 0.2861 0.070 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 0.02703(16) 0.03967(18) 0.0490(2) -0.00410(14) 0.01522(12) -0.00146(13) N1 0.0382(12) 0.0459(13) 0.0582(15) 0.0011(11) 0.0200(11) -0.0036(10) N2 0.0471(13) 0.0426(13) 0.0515(14) 0.0035(11) 0.0179(11) -0.0028(10) N3 0.0572(14) 0.0391(13) 0.0469(14) 0.0034(11) 0.0194(11) 0.0062(11) N4 0.0405(12) 0.0342(12) 0.0467(13) 0.0021(10) 0.0120(10) -0.0009(9) O1 0.0271(9) 0.0535(11) 0.0603(12) -0.0137(9) 0.0188(8) -0.0033(8) O2 0.0394(10) 0.0376(10) 0.0800(14) -0.0052(10) 0.0226(10) -0.0013(8) O3 0.0453(12) 0.0721(15) 0.130(2) 0.0189(14) 0.0494(14) 0.0009(11) O4 0.0300(9) 0.0508(12) 0.0791(14) -0.0056(10) 0.0221(9) 0.0035(8) C1 0.0265(12) 0.0366(14) 0.0359(14) -0.0019(11) 0.0090(10) -0.0009(10) C2 0.0290(12) 0.0367(14) 0.0371(14) -0.0027(11) 0.0079(10) 0.0023(10) C3 0.0248(12) 0.0424(15) 0.0402(14) -0.0033(11) 0.0095(10) -0.0018(10) C4 0.0350(14) 0.0413(15) 0.0604(18) -0.0042(13) 0.0151(13) -0.0075(12) C5 0.0424(15) 0.0364(14) 0.0640(19) -0.0048(13) 0.0211(14) 0.0012(12) C6 0.0319(13) 0.0453(15) 0.0545(17) -0.0010(13) 0.0173(12) 0.0047(11) C7 0.0293(13) 0.0435(15) 0.0377(15) 0.0008(12) 0.0090(11) 0.0008(11) C8 0.0275(13) 0.0548(17) 0.0469(16) -0.0077(14) 0.0106(12) -0.0027(12) C9 0.066(2) 0.0408(18) 0.125(3) -0.0069(18) 0.043(2) 0.0014(15) C10 0.064(2) 0.056(2) 0.110(3) 0.0058(19) 0.055(2) 0.0025(16) C11 0.074(2) 0.055(2) 0.111(3) 0.0134(19) 0.058(2) -0.0018(17) C12 0.0423(15) 0.0523(17) 0.0543(18) 0.0087(14) 0.0206(13) 0.0022(13) C13 0.0525(17) 0.0507(17) 0.0529(18) 0.0050(14) 0.0117(14) 0.0002(14) C14 0.0580(17) 0.0489(17) 0.0403(16) 0.0065(13) 0.0114(13) -0.0021(14) C15 0.0630(19) 0.0535(18) 0.0493(18) 0.0098(14) 0.0149(15) 0.0018(14) C16 0.0644(19) 0.0508(18) 0.064(2) 0.0152(15) 0.0219(16) 0.0075(15) C17 0.076(2) 0.0566(19) 0.0555(19) 0.0145(15) 0.0319(16) 0.0096(16) C18 0.0476(16) 0.0386(15) 0.0464(16) -0.0053(13) 0.0159(13) -0.0039(12) C19 0.069(2) 0.0316(15) 0.060(2) -0.0006(14) 0.0092(16) -0.0062(14) C20 0.082(2) 0.0395(17) 0.0498(18) -0.0096(14) 0.0071(16) 0.0061(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 1.9326(16) 1_655 ? Zn1 O1 1.9434(16) . ? Zn1 N4 1.999(2) 4_566 ? Zn1 N1 2.003(2) . ? N1 C12 1.313(3) . ? N1 C10 1.370(3) . ? N2 C12 1.324(3) . ? N2 C11 1.356(3) . ? N2 C13 1.468(3) . ? N3 C18 1.330(3) . ? N3 C20 1.363(3) . ? N3 C17 1.463(3) . ? N4 C18 1.310(3) . ? N4 C19 1.362(3) . ? N4 Zn1 1.999(2) 4_565 ? O1 C7 1.285(3) . ? O2 C7 1.234(3) . ? O3 C8 1.214(3) . ? O4 C8 1.277(3) . ? O4 Zn1 1.9326(16) 1_455 ? C1 C6 1.386(3) . ? C1 C2 1.393(3) . ? C1 C7 1.502(3) . ? C2 C3 1.384(3) . ? C2 H2 0.9300 . ? C3 C4 1.384(3) . ? C3 C8 1.509(3) . ? C4 C5 1.389(3) . ? C4 H4 0.9300 . ? C5 C6 1.391(3) . ? C5 C9 1.513(4) . ? C6 H6 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.352(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.505(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.521(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.509(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.516(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18 0.9300 . ? C19 C20 1.342(4) . ? C19 H19 0.9300 . ? C20 H20 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 O4 Zn1 O1 113.14(7) 1_655 . ? O4 Zn1 N4 112.73(8) 1_655 4_566 ? O1 Zn1 N4 107.60(8) . 4_566 ? O4 Zn1 N1 97.31(8) 1_655 . ? O1 Zn1 N1 116.14(8) . . ? N4 Zn1 N1 109.79(9) 4_566 . ? C12 N1 C10 104.9(2) . . ? C12 N1 Zn1 130.09(17) . . ? C10 N1 Zn1 124.95(19) . . ? C12 N2 C11 106.6(2) . . ? C12 N2 C13 125.4(2) . . ? C11 N2 C13 127.9(2) . . ? C18 N3 C20 106.6(2) . . ? C18 N3 C17 126.3(2) . . ? C20 N3 C17 127.0(2) . . ? C18 N4 C19 105.2(2) . . ? C18 N4 Zn1 126.77(18) . 4_565 ? C19 N4 Zn1 127.76(18) . 4_565 ? C7 O1 Zn1 114.35(15) . . ? C8 O4 Zn1 120.81(16) . 1_455 ? C6 C1 C2 118.6(2) . . ? C6 C1 C7 121.0(2) . . ? C2 C1 C7 120.3(2) . . ? C3 C2 C1 120.5(2) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.8(2) . . ? C2 C3 C8 120.1(2) . . ? C4 C3 C8 120.0(2) . . ? C3 C4 C5 121.0(2) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 118.2(2) . . ? C4 C5 C9 120.8(2) . . ? C6 C5 C9 121.1(2) . . ? C1 C6 C5 121.9(2) . . ? C1 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? O2 C7 O1 124.4(2) . . ? O2 C7 C1 120.6(2) . . ? O1 C7 C1 115.0(2) . . ? O3 C8 O4 124.6(2) . . ? O3 C8 C3 120.9(3) . . ? O4 C8 C3 114.5(2) . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 N1 109.1(3) . . ? C11 C10 H10 125.5 . . ? N1 C10 H10 125.5 . . ? C10 C11 N2 106.9(3) . . ? C10 C11 H11 126.6 . . ? N2 C11 H11 126.6 . . ? N1 C12 N2 112.5(2) . . ? N1 C12 H12 123.7 . . ? N2 C12 H12 123.7 . . ? N2 C13 C14 112.8(2) . . ? N2 C13 H13A 109.0 . . ? C14 C13 H13A 109.0 . . ? N2 C13 H13B 109.0 . . ? C14 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C13 C14 C15 110.9(2) . . ? C13 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C16 C15 C14 112.8(2) . . ? C16 C15 H15A 109.0 . . ? C14 C15 H15A 109.0 . . ? C16 C15 H15B 109.0 . . ? C14 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C15 C16 C17 111.8(2) . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16B 109.3 . . ? C17 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? N3 C17 C16 112.9(2) . . ? N3 C17 H17A 109.0 . . ? C16 C17 H17A 109.0 . . ? N3 C17 H17B 109.0 . . ? C16 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? N4 C18 N3 112.0(2) . . ? N4 C18 H18 124.0 . . ? N3 C18 H18 124.0 . . ? C20 C19 N4 109.8(2) . . ? C20 C19 H19 125.1 . . ? N4 C19 H19 125.1 . . ? C19 C20 N3 106.4(3) . . ? C19 C20 H20 126.8 . . ? N3 C20 H20 126.8 . . ? 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 O4 Zn1 N1 C12 -174.8(2) 1_655 . . . ? O1 Zn1 N1 C12 64.9(3) . . . . ? N4 Zn1 N1 C12 -57.4(3) 4_566 . . . ? O4 Zn1 N1 C10 6.5(3) 1_655 . . . ? O1 Zn1 N1 C10 -113.8(2) . . . . ? N4 Zn1 N1 C10 123.9(2) 4_566 . . . ? O4 Zn1 O1 C7 177.58(16) 1_655 . . . ? N4 Zn1 O1 C7 52.38(19) 4_566 . . . ? N1 Zn1 O1 C7 -71.08(19) . . . . ? C6 C1 C2 C3 2.0(4) . . . . ? C7 C1 C2 C3 -175.0(2) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? C1 C2 C3 C8 177.1(2) . . . . ? C2 C3 C4 C5 -2.4(4) . . . . ? C8 C3 C4 C5 -179.7(2) . . . . ? C3 C4 C5 C6 3.0(4) . . . . ? C3 C4 C5 C9 -177.4(3) . . . . ? C2 C1 C6 C5 -1.3(4) . . . . ? C7 C1 C6 C5 175.7(2) . . . . ? C4 C5 C6 C1 -1.1(4) . . . . ? C9 C5 C6 C1 179.3(3) . . . . ? Zn1 O1 C7 O2 24.1(3) . . . . ? Zn1 O1 C7 C1 -153.39(16) . . . . ? C6 C1 C7 O2 -170.7(2) . . . . ? C2 C1 C7 O2 6.3(4) . . . . ? C6 C1 C7 O1 6.9(3) . . . . ? C2 C1 C7 O1 -176.1(2) . . . . ? Zn1 O4 C8 O3 4.2(4) 1_455 . . . ? Zn1 O4 C8 C3 -177.18(15) 1_455 . . . ? C2 C3 C8 O3 -161.2(3) . . . . ? C4 C3 C8 O3 16.2(4) . . . . ? C2 C3 C8 O4 20.1(3) . . . . ? C4 C3 C8 O4 -162.6(2) . . . . ? C12 N1 C10 C11 0.0(4) . . . . ? Zn1 N1 C10 C11 178.9(2) . . . . ? N1 C10 C11 N2 0.3(4) . . . . ? C12 N2 C11 C10 -0.4(4) . . . . ? C13 N2 C11 C10 -177.7(3) . . . . ? C10 N1 C12 N2 -0.3(3) . . . . ? Zn1 N1 C12 N2 -179.15(18) . . . . ? C11 N2 C12 N1 0.4(3) . . . . ? C13 N2 C12 N1 177.8(2) . . . . ? C12 N2 C13 C14 153.7(3) . . . . ? C11 N2 C13 C14 -29.5(4) . . . . ? N2 C13 C14 C15 -172.6(2) . . . . ? C13 C14 C15 C16 -164.7(2) . . . . ? C14 C15 C16 C17 178.3(3) . . . . ? C18 N3 C17 C16 57.4(4) . . . . ? C20 N3 C17 C16 -125.4(3) . . . . ? C15 C16 C17 N3 -157.9(3) . . . . ? C19 N4 C18 N3 -0.4(3) . . . . ? Zn1 N4 C18 N3 -175.13(16) 4_565 . . . ? C20 N3 C18 N4 0.5(3) . . . . ? C17 N3 C18 N4 178.1(2) . . . . ? C18 N4 C19 C20 0.3(3) . . . . ? Zn1 N4 C19 C20 174.87(19) 4_565 . . . ? N4 C19 C20 N3 0.0(3) . . . . ? C18 N3 C20 C19 -0.3(3) . . . . ? C17 N3 C20 C19 -177.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.281 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.049 # Attachment '- 2.cif' data_bb _database_code_depnum_ccdc_archive 'CCDC 762923' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 N4 O4 Zn' _chemical_formula_weight 461.81 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.6105(10) _cell_length_b 15.2014(16) _cell_length_c 14.4610(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.6450(10) _cell_angle_gamma 90.00 _cell_volume 2112.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3154 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 24.47 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 1.198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7005 _exptl_absorpt_correction_T_max 0.8044 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 15849 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3934 _reflns_number_gt 2902 _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^)+(0.0505P)^2^+1.7140P] 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 3934 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1156 _refine_ls_wR_factor_gt 0.1036 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 C13 C 0.0811(4) 0.7359(3) -0.0071(3) 0.088(2) Uani 0.724(4) 1 d PG A 1 H13A H 0.0680 0.7739 0.0461 0.106 Uiso 0.724(4) 1 calc PR A 1 H13B H -0.0101 0.7188 -0.0301 0.106 Uiso 0.724(4) 1 calc PR A 1 C14 C 0.1591(4) 0.6557(2) 0.0225(2) 0.0800(19) Uani 0.724(4) 1 d PG A 1 H14A H 0.1066 0.6277 0.0712 0.096 Uiso 0.724(4) 1 calc PR A 1 H14B H 0.1599 0.6153 -0.0295 0.096 Uiso 0.724(4) 1 calc PR A 1 C15 C 0.3042(3) 0.6657(3) 0.0559(2) 0.0756(17) Uani 0.724(4) 1 d PG A 1 H15A H 0.3544 0.6991 0.0099 0.091 Uiso 0.724(4) 1 calc PR A 1 H15B H 0.3456 0.6076 0.0584 0.091 Uiso 0.724(4) 1 calc PR A 1 C16 C 0.3290(3) 0.7085(2) 0.14715(17) 0.0760(17) Uani 0.724(4) 1 d PG A 1 H16A H 0.3034 0.7700 0.1421 0.091 Uiso 0.724(4) 1 calc PR A 1 H16B H 0.4278 0.7060 0.1613 0.091 Uiso 0.724(4) 1 calc PR A 1 C17 C 0.2497(3) 0.6679(2) 0.22820(18) 0.0700(15) Uani 0.724(4) 1 d PG A 1 H17A H 0.1528 0.6855 0.2244 0.084 Uiso 0.724(4) 1 calc PR A 1 H17B H 0.2534 0.6043 0.2237 0.084 Uiso 0.724(4) 1 calc PR A 1 C18 C 0.3105(4) 0.6965(3) 0.3207(2) 0.0749(18) Uani 0.724(4) 1 d PG A 1 H18A H 0.4083 0.6810 0.3238 0.090 Uiso 0.724(4) 1 calc PR A 1 H18B H 0.3029 0.7598 0.3267 0.090 Uiso 0.724(4) 1 calc PR A 1 C13' C 0.1042(4) 0.7078(3) -0.0281(3) 0.088(2) Uani 0.276(4) 1 d PG A 2 H13C H 0.1440 0.6543 -0.0532 0.106 Uiso 0.276(4) 1 calc PR A 2 H13D H 0.0037 0.7038 -0.0337 0.106 Uiso 0.276(4) 1 calc PR A 2 C14' C 0.1465(3) 0.7178(2) 0.0729(2) 0.0800(19) Uani 0.276(4) 1 d PG A 2 H14C H 0.1273 0.7768 0.0948 0.096 Uiso 0.276(4) 1 calc PR A 2 H14D H 0.0974 0.6759 0.1112 0.096 Uiso 0.276(4) 1 calc PR A 2 C15' C 0.3012(3) 0.6994(3) 0.07401(19) 0.0756(17) Uani 0.276(4) 1 d PG A 2 H15C H 0.3193 0.6370 0.0668 0.091 Uiso 0.276(4) 1 calc PR A 2 H15D H 0.3472 0.7312 0.0249 0.091 Uiso 0.276(4) 1 calc PR A 2 C16' C 0.3507(3) 0.7314(2) 0.16783(19) 0.0760(17) Uani 0.276(4) 1 d PG A 2 H16C H 0.3567 0.7950 0.1693 0.091 Uiso 0.276(4) 1 calc PR A 2 H16D H 0.4410 0.7068 0.1836 0.091 Uiso 0.276(4) 1 calc PR A 2 C17' C 0.2392(3) 0.6981(2) 0.23368(18) 0.0700(15) Uani 0.276(4) 1 d PG A 2 H17C H 0.1811 0.7460 0.2549 0.084 Uiso 0.276(4) 1 calc PR A 2 H17D H 0.1808 0.6541 0.2041 0.084 Uiso 0.276(4) 1 calc PR A 2 C18' C 0.3225(4) 0.6588(3) 0.3128(3) 0.0749(18) Uani 0.276(4) 1 d PG A 2 H18C H 0.3544 0.6005 0.2957 0.090 Uiso 0.276(4) 1 calc PR A 2 H18D H 0.4036 0.6950 0.3254 0.090 Uiso 0.276(4) 1 calc PR A 2 Zn1 Zn 0.28035(4) 1.03602(3) -0.15835(3) 0.04407(15) Uani 1 1 d . . . O1 O 0.4205(3) 1.0003(3) -0.3334(2) 0.1032(13) Uani 1 1 d . . . O2 O 0.4674(2) 1.06245(19) -0.20037(19) 0.0633(8) Uani 1 1 d . . . O3 O 0.9816(2) 1.0581(2) -0.12039(18) 0.0629(8) Uani 1 1 d . . . O4 O 1.1288(2) 1.08351(18) -0.23434(17) 0.0550(7) Uani 1 1 d . . . N1 N 0.2403(3) 0.9069(2) -0.1427(2) 0.0502(7) Uani 1 1 d . A . N2 N 0.1559(4) 0.7865(2) -0.0813(3) 0.0733(10) Uani 1 1 d . . . C12 C 0.2082(6) 0.7647(3) -0.1640(4) 0.0870(16) Uani 1 1 d . A . H12 H 0.2090 0.7086 -0.1898 0.104 Uiso 1 1 calc R . . N4 N 0.2347(3) 0.6527(3) 0.3987(2) 0.0664(9) Uani 1 1 d . . . C21 C 0.0980(5) 0.6643(4) 0.4166(3) 0.0886(16) Uani 1 1 d . A . H21 H 0.0331 0.6930 0.3792 0.106 Uiso 1 1 calc R . . N6 N 0.1960(3) 0.5910(2) 0.5329(2) 0.0496(7) Uani 1 1 d . . . C1 C 0.6471(3) 1.0570(2) -0.3096(2) 0.0407(8) Uani 1 1 d . . . C2 C 0.7535(3) 1.0630(2) -0.2444(2) 0.0399(8) Uani 1 1 d . . . H2 H 0.7336 1.0578 -0.1819 0.048 Uiso 1 1 calc R . . C3 C 0.8900(3) 1.0767(2) -0.2721(2) 0.0408(8) Uani 1 1 d . . . C4 C 0.9158(3) 1.0875(2) -0.3664(2) 0.0474(9) Uani 1 1 d . . . H4 H 1.0063 1.0978 -0.3856 0.057 Uiso 1 1 calc R . . C5 C 0.8092(4) 1.0834(3) -0.4321(2) 0.0500(9) Uani 1 1 d . . . C6 C 0.6769(3) 1.0651(2) -0.4021(2) 0.0455(8) Uani 1 1 d . . . H6 H 0.6056 1.0581 -0.4455 0.055 Uiso 1 1 calc R . . C7 C 0.4998(3) 1.0377(3) -0.2803(3) 0.0488(9) Uani 1 1 d . . . C8 C 1.0072(3) 1.0735(2) -0.2022(3) 0.0452(8) Uani 1 1 d . . . C9 C 0.8377(4) 1.0964(4) -0.5340(3) 0.0797(14) Uani 1 1 d . . . H9A H 0.7728 1.0624 -0.5700 0.120 Uiso 1 1 calc R . . H9B H 0.9308 1.0777 -0.5471 0.120 Uiso 1 1 calc R . . H9C H 0.8276 1.1576 -0.5493 0.120 Uiso 1 1 calc R . . C10 C 0.1784(4) 0.8716(3) -0.0710(3) 0.0563(10) Uani 1 1 d . A . H10 H 0.1531 0.9032 -0.0187 0.068 Uiso 1 1 calc R . . C11 C 0.2596(5) 0.8388(3) -0.2033(3) 0.0731(12) Uani 1 1 d . . . H11 H 0.3007 0.8427 -0.2611 0.088 Uiso 1 1 calc R A . C19 C 0.2881(4) 0.6082(3) 0.4696(3) 0.0598(10) Uani 1 1 d . A . H19 H 0.3809 0.5910 0.4737 0.072 Uiso 1 1 calc R . . C20 C 0.0742(4) 0.6263(3) 0.4986(3) 0.0792(14) Uani 1 1 d . A . H20 H -0.0114 0.6242 0.5278 0.095 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 C13 0.063(3) 0.042(4) 0.160(6) 0.028(4) 0.010(4) -0.010(3) C14 0.077(4) 0.097(5) 0.065(4) 0.017(3) 0.001(3) 0.007(4) C15 0.075(3) 0.073(5) 0.079(4) 0.004(3) 0.004(3) -0.001(3) C16 0.093(4) 0.072(4) 0.064(4) -0.025(3) 0.026(3) -0.032(3) C17 0.087(3) 0.055(4) 0.067(3) 0.003(3) 0.003(3) -0.014(3) C18 0.077(3) 0.081(5) 0.067(3) -0.003(3) 0.007(3) -0.022(3) C13' 0.063(3) 0.042(4) 0.160(6) 0.028(4) 0.010(4) -0.010(3) C14' 0.077(4) 0.097(5) 0.065(4) 0.017(3) 0.001(3) 0.007(4) C15' 0.075(3) 0.073(5) 0.079(4) 0.004(3) 0.004(3) -0.001(3) C16' 0.093(4) 0.072(4) 0.064(4) -0.025(3) 0.026(3) -0.032(3) C17' 0.087(3) 0.055(4) 0.067(3) 0.003(3) 0.003(3) -0.014(3) C18' 0.077(3) 0.081(5) 0.067(3) -0.003(3) 0.007(3) -0.022(3) Zn1 0.0255(2) 0.0576(3) 0.0491(3) 0.0050(2) 0.00116(15) -0.00434(18) O1 0.0465(17) 0.192(4) 0.071(2) -0.022(2) -0.0001(15) -0.048(2) O2 0.0327(13) 0.094(2) 0.0633(18) -0.0077(15) 0.0117(12) -0.0120(13) O3 0.0363(13) 0.105(2) 0.0476(15) 0.0086(15) -0.0018(11) -0.0087(14) O4 0.0256(12) 0.0777(18) 0.0618(16) 0.0184(14) 0.0015(11) -0.0034(12) N1 0.0393(16) 0.0559(19) 0.0552(19) 0.0012(16) -0.0042(14) -0.0025(14) N2 0.061(2) 0.057(2) 0.101(3) 0.010(2) -0.014(2) -0.0076(18) C12 0.091(4) 0.046(3) 0.124(5) -0.010(3) -0.037(3) -0.002(3) N4 0.054(2) 0.089(3) 0.057(2) 0.0084(19) 0.0030(16) -0.0087(18) C21 0.061(3) 0.127(4) 0.078(3) 0.037(3) -0.001(2) 0.017(3) N6 0.0339(15) 0.062(2) 0.0525(18) 0.0014(15) 0.0010(13) 0.0044(14) C1 0.0281(16) 0.044(2) 0.050(2) 0.0041(15) 0.0024(14) 0.0007(14) C2 0.0293(16) 0.046(2) 0.0442(18) 0.0036(15) 0.0053(14) -0.0004(14) C3 0.0285(16) 0.045(2) 0.049(2) 0.0043(16) 0.0010(14) 0.0011(14) C4 0.0287(16) 0.062(2) 0.052(2) 0.0011(18) 0.0108(15) -0.0016(16) C5 0.0393(19) 0.066(2) 0.045(2) 0.0044(18) 0.0024(16) 0.0014(17) C6 0.0326(17) 0.056(2) 0.048(2) 0.0016(17) -0.0061(15) 0.0016(15) C7 0.0260(16) 0.064(2) 0.056(2) 0.009(2) -0.0014(16) -0.0024(16) C8 0.0281(17) 0.053(2) 0.054(2) 0.0064(17) 0.0000(15) -0.0054(15) C9 0.059(3) 0.134(4) 0.046(2) 0.005(3) 0.003(2) -0.016(3) C10 0.042(2) 0.053(2) 0.074(3) 0.008(2) -0.0020(18) -0.0071(18) C11 0.074(3) 0.080(3) 0.066(3) -0.018(3) -0.013(2) 0.005(3) C19 0.040(2) 0.079(3) 0.060(2) 0.002(2) -0.0007(18) 0.002(2) C20 0.040(2) 0.120(4) 0.077(3) 0.027(3) 0.007(2) 0.019(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C13 C14 1.4918(17) . ? C13 N2 1.509(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.4783(17) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.4875(17) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.5349(18) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.5170(18) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 N4 1.505(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C13' N2 1.509(5) . ? C13' C14' 1.5195(18) . ? C13' H13C 0.9700 . ? C13' H13D 0.9700 . ? C14' C15' 1.5131(18) . ? C14' H14C 0.9700 . ? C14' H14D 0.9700 . ? C15' C16' 1.5126(18) . ? C15' H15C 0.9700 . ? C15' H15D 0.9700 . ? C16' C17' 1.5275(18) . ? C16' H16C 0.9700 . ? C16' H16D 0.9700 . ? C17' C18' 1.5125(18) . ? C17' H17C 0.9700 . ? C17' H17D 0.9700 . ? C18' N4 1.513(5) . ? C18' H18C 0.9700 . ? C18' H18D 0.9700 . ? Zn1 O2 1.946(2) . ? Zn1 O4 1.953(2) 1_455 ? Zn1 N6 2.008(3) 2 ? Zn1 N1 2.014(3) . ? O1 C7 1.216(4) . ? O2 C7 1.258(4) . ? O3 C8 1.233(4) . ? O4 C8 1.273(4) . ? O4 Zn1 1.953(2) 1_655 ? N1 C10 1.315(5) . ? N1 C11 1.371(5) . ? N2 C10 1.320(5) . ? N2 C12 1.344(6) . ? C12 C11 1.358(7) . ? C12 H12 0.9300 . ? N4 C19 1.326(5) . ? N4 C21 1.353(5) . ? C21 C20 1.340(6) . ? C21 H21 0.9300 . ? N6 C19 1.307(5) . ? N6 C20 1.375(5) . ? N6 Zn1 2.008(3) 2_545 ? C1 C6 1.377(5) . ? C1 C2 1.385(5) . ? C1 C7 1.510(4) . ? C2 C3 1.392(4) . ? C2 H2 0.9300 . ? C3 C4 1.398(5) . ? C3 C8 1.506(5) . ? C4 C5 1.390(5) . ? C4 H4 0.9300 . ? C5 C6 1.377(5) . ? C5 C9 1.515(5) . ? C6 H6 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C19 H19 0.9300 . ? C20 H20 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 C14 C13 N2 112.2(3) . . ? C14 C13 H13A 109.2 . . ? N2 C13 H13A 109.2 . . ? C14 C13 H13B 109.2 . . ? N2 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C15 C14 C13 118.6 . . ? C15 C14 H14A 107.7 . . ? C13 C14 H14A 107.7 . . ? C15 C14 H14B 107.7 . . ? C13 C14 H14B 107.7 . . ? H14A C14 H14B 107.1 . . ? C14 C15 C16 118.5 . . ? C14 C15 H15A 107.7 . . ? C16 C15 H15A 107.7 . . ? C14 C15 H15B 107.7 . . ? C16 C15 H15B 107.7 . . ? H15A C15 H15B 107.1 . . ? C15 C16 C17 115.2 . . ? C15 C16 H16A 108.5 . . ? C17 C16 H16A 108.5 . . ? C15 C16 H16B 108.5 . . ? C17 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C18 C17 C16 111.6 . . ? C18 C17 H17A 109.3 . . ? C16 C17 H17A 109.3 . . ? C18 C17 H17B 109.3 . . ? C16 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? N4 C18 C17 110.5(2) . . ? N4 C18 H18A 109.6 . . ? C17 C18 H18A 109.6 . . ? N4 C18 H18B 109.6 . . ? C17 C18 H18B 109.6 . . ? H18A C18 H18B 108.1 . . ? N2 C13' C14' 108.9(3) . . ? N2 C13' H13C 109.9 . . ? C14' C13' H13C 109.9 . . ? N2 C13' H13D 109.9 . . ? C14' C13' H13D 109.9 . . ? H13C C13' H13D 108.3 . . ? C15' C14' C13' 104.1 . . ? C15' C14' H14C 110.9 . . ? C13' C14' H14C 110.9 . . ? C15' C14' H14D 110.9 . . ? C13' C14' H14D 110.9 . . ? H14C C14' H14D 109.0 . . ? C16' C15' C14' 104.4 . . ? C16' C15' H15C 110.9 . . ? C14' C15' H15C 110.9 . . ? C16' C15' H15D 110.9 . . ? C14' C15' H15D 110.9 . . ? H15C C15' H15D 108.9 . . ? C15' C16' C17' 103.7 . . ? C15' C16' H16C 111.0 . . ? C17' C16' H16C 111.0 . . ? C15' C16' H16D 111.0 . . ? C17' C16' H16D 111.0 . . ? H16C C16' H16D 109.0 . . ? C18' C17' C16' 103.5 . . ? C18' C17' H17C 111.1 . . ? C16' C17' H17C 111.1 . . ? C18' C17' H17D 111.1 . . ? C16' C17' H17D 111.1 . . ? H17C C17' H17D 109.0 . . ? N4 C18' C17' 110.5(3) . . ? N4 C18' H18C 109.5 . . ? C17' C18' H18C 109.5 . . ? N4 C18' H18D 109.5 . . ? C17' C18' H18D 109.5 . . ? H18C C18' H18D 108.1 . . ? O2 Zn1 O4 115.70(11) . 1_455 ? O2 Zn1 N6 95.77(11) . 2 ? O4 Zn1 N6 115.52(12) 1_455 2 ? O2 Zn1 N1 114.52(12) . . ? O4 Zn1 N1 106.34(11) 1_455 . ? N6 Zn1 N1 108.89(12) 2 . ? C7 O2 Zn1 117.6(2) . . ? C8 O4 Zn1 115.6(2) . 1_655 ? C10 N1 C11 105.2(4) . . ? C10 N1 Zn1 125.1(3) . . ? C11 N1 Zn1 129.5(3) . . ? C10 N2 C12 106.3(4) . . ? C10 N2 C13 119.8(4) . . ? C12 N2 C13 133.9(4) . . ? C10 N2 C13' 140.7(4) . . ? C12 N2 C13' 112.7(4) . . ? C13 N2 C13' 21.85(8) . . ? N2 C12 C11 108.0(4) . . ? N2 C12 H12 126.0 . . ? C11 C12 H12 126.0 . . ? C19 N4 C21 106.7(3) . . ? C19 N4 C18 128.2(3) . . ? C21 N4 C18 124.4(4) . . ? C19 N4 C18' 116.8(3) . . ? C21 N4 C18' 134.5(4) . . ? C18 N4 C18' 22.78(8) . . ? C20 C21 N4 106.8(4) . . ? C20 C21 H21 126.6 . . ? N4 C21 H21 126.6 . . ? C19 N6 C20 104.5(3) . . ? C19 N6 Zn1 130.2(3) . 2_545 ? C20 N6 Zn1 125.1(3) . 2_545 ? C6 C1 C2 119.6(3) . . ? C6 C1 C7 119.7(3) . . ? C2 C1 C7 120.6(3) . . ? C1 C2 C3 120.4(3) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C2 C3 C4 118.4(3) . . ? C2 C3 C8 120.2(3) . . ? C4 C3 C8 121.3(3) . . ? C5 C4 C3 121.6(3) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C6 C5 C4 118.0(3) . . ? C6 C5 C9 120.7(3) . . ? C4 C5 C9 121.2(3) . . ? C1 C6 C5 121.8(3) . . ? C1 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? O1 C7 O2 124.1(3) . . ? O1 C7 C1 119.7(3) . . ? O2 C7 C1 116.2(3) . . ? O3 C8 O4 124.6(3) . . ? O3 C8 C3 119.7(3) . . ? O4 C8 C3 115.7(3) . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 N2 112.7(4) . . ? N1 C10 H10 123.6 . . ? N2 C10 H10 123.6 . . ? C12 C11 N1 107.9(4) . . ? C12 C11 H11 126.1 . . ? N1 C11 H11 126.1 . . ? N6 C19 N4 112.5(3) . . ? N6 C19 H19 123.7 . . ? N4 C19 H19 123.7 . . ? C21 C20 N6 109.5(4) . . ? C21 C20 H20 125.2 . . ? N6 C20 H20 125.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C13 C14 C15 55.9(3) . . . . ? C13 C14 C15 C16 70.6 . . . . ? C14 C15 C16 C17 53.9 . . . . ? C15 C16 C17 C18 163.5 . . . . ? C16 C17 C18 N4 -177.6(3) . . . . ? N2 C13' C14' C15' -73.8(3) . . . . ? C13' C14' C15' C16' 166.1 . . . . ? C14' C15' C16' C17' 43.0 . . . . ? C15' C16' C17' C18' 133.9 . . . . ? C16' C17' C18' N4 159.3(3) . . . . ? O4 Zn1 O2 C7 -58.5(3) 1_455 . . . ? N6 Zn1 O2 C7 179.6(3) 2 . . . ? N1 Zn1 O2 C7 65.8(3) . . . . ? O2 Zn1 N1 C10 134.2(3) . . . . ? O4 Zn1 N1 C10 -96.7(3) 1_455 . . . ? N6 Zn1 N1 C10 28.4(3) 2 . . . ? O2 Zn1 N1 C11 -51.1(4) . . . . ? O4 Zn1 N1 C11 78.0(3) 1_455 . . . ? N6 Zn1 N1 C11 -156.9(3) 2 . . . ? C14 C13 N2 C10 -128.5(3) . . . . ? C14 C13 N2 C12 53.1(5) . . . . ? C14 C13 N2 C13' 36.79(15) . . . . ? C14' C13' N2 C10 -33.5(6) . . . . ? C14' C13' N2 C12 138.8(3) . . . . ? C14' C13' N2 C13 -53.86(13) . . . . ? C10 N2 C12 C11 -1.2(5) . . . . ? C13 N2 C12 C11 177.4(4) . . . . ? C13' N2 C12 C11 -176.1(4) . . . . ? C17 C18 N4 C19 128.7(4) . . . . ? C17 C18 N4 C21 -62.5(5) . . . . ? C17 C18 N4 C18' 61.77(14) . . . . ? C17' C18' N4 C19 170.8(3) . . . . ? C17' C18' N4 C21 9.5(6) . . . . ? C17' C18' N4 C18 -63.31(13) . . . . ? C19 N4 C21 C20 0.4(6) . . . . ? C18 N4 C21 C20 -170.5(4) . . . . ? C18' N4 C21 C20 162.9(5) . . . . ? C6 C1 C2 C3 -0.3(5) . . . . ? C7 C1 C2 C3 177.0(3) . . . . ? C1 C2 C3 C4 2.4(5) . . . . ? C1 C2 C3 C8 -173.5(3) . . . . ? C2 C3 C4 C5 -1.1(5) . . . . ? C8 C3 C4 C5 174.7(3) . . . . ? C3 C4 C5 C6 -2.2(6) . . . . ? C3 C4 C5 C9 179.1(4) . . . . ? C2 C1 C6 C5 -3.2(5) . . . . ? C7 C1 C6 C5 179.4(3) . . . . ? C4 C5 C6 C1 4.4(6) . . . . ? C9 C5 C6 C1 -177.0(4) . . . . ? Zn1 O2 C7 O1 1.7(6) . . . . ? Zn1 O2 C7 C1 -178.3(2) . . . . ? C6 C1 C7 O1 25.5(6) . . . . ? C2 C1 C7 O1 -151.9(4) . . . . ? C6 C1 C7 O2 -154.5(3) . . . . ? C2 C1 C7 O2 28.1(5) . . . . ? Zn1 O4 C8 O3 19.4(5) 1_655 . . . ? Zn1 O4 C8 C3 -157.3(2) 1_655 . . . ? C2 C3 C8 O3 0.5(5) . . . . ? C4 C3 C8 O3 -175.2(4) . . . . ? C2 C3 C8 O4 177.4(3) . . . . ? C4 C3 C8 O4 1.7(5) . . . . ? C11 N1 C10 N2 -0.4(4) . . . . ? Zn1 N1 C10 N2 175.3(2) . . . . ? C12 N2 C10 N1 1.0(5) . . . . ? C13 N2 C10 N1 -177.8(3) . . . . ? C13' N2 C10 N1 173.6(4) . . . . ? N2 C12 C11 N1 1.0(5) . . . . ? C10 N1 C11 C12 -0.4(5) . . . . ? Zn1 N1 C11 C12 -175.8(3) . . . . ? C20 N6 C19 N4 1.0(5) . . . . ? Zn1 N6 C19 N4 -173.9(3) 2_545 . . . ? C21 N4 C19 N6 -0.9(5) . . . . ? C18 N4 C19 N6 169.5(4) . . . . ? C18' N4 C19 N6 -167.0(3) . . . . ? N4 C21 C20 N6 0.2(6) . . . . ? C19 N6 C20 C21 -0.7(6) . . . . ? Zn1 N6 C20 C21 174.5(3) 2_545 . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.426 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.059 # Attachment '- 4.cif' data_a _database_code_depnum_ccdc_archive 'CCDC 762924' #TrackingRef '- 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 N4 O5 Zn' _chemical_formula_weight 435.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.4763(14) _cell_length_b 13.2934(11) _cell_length_c 17.2155(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3770.6(6) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4211 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 22.90 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 1.341 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7660 _exptl_absorpt_correction_T_max 0.9120 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 27180 _diffrn_reflns_av_R_equivalents 0.0523 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3501 _reflns_number_gt 2670 _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^)+(0.0296P)^2^+5.0363P] 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 3501 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0857 _refine_ls_wR_factor_gt 0.0760 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.290873(19) 0.19056(2) 0.120308(18) 0.02758(11) Uani 1 1 d . . . O1 O 0.16436(13) 0.05679(17) 0.18260(13) 0.0458(6) Uani 1 1 d . . . O2 O 0.17914(12) 0.16574(15) 0.08559(13) 0.0377(5) Uani 1 1 d . . . O3 O -0.05192(13) 0.23654(17) -0.09158(14) 0.0462(6) Uani 1 1 d . . . O4 O -0.17497(12) 0.20422(15) -0.04589(12) 0.0356(5) Uani 1 1 d . . . O5 O -0.12818(13) -0.06621(19) 0.14961(15) 0.0540(7) Uani 1 1 d . . . N1 N 0.29611(14) 0.24386(18) 0.22862(13) 0.0322(6) Uani 1 1 d . . . N2 N 0.30719(14) 0.34094(19) 0.33077(14) 0.0331(6) Uani 1 1 d . . . N3 N 0.54856(15) 0.45040(18) 0.40040(16) 0.0401(7) Uani 1 1 d . . . N4 N 0.64793(14) 0.55984(18) 0.39285(14) 0.0330(6) Uani 1 1 d . . . C1 C 0.05063(16) 0.0894(2) 0.10137(16) 0.0276(6) Uani 1 1 d . . . C2 C 0.01838(17) 0.1433(2) 0.04001(17) 0.0288(6) Uani 1 1 d . . . H2 H 0.0508 0.1884 0.0129 0.035 Uiso 1 1 calc R . . C3 C -0.06264(16) 0.1302(2) 0.01856(16) 0.0275(6) Uani 1 1 d . . . C4 C -0.10951(17) 0.0606(2) 0.05755(17) 0.0328(7) Uani 1 1 d . . . H4 H -0.1636 0.0517 0.0436 0.039 Uiso 1 1 calc R . . C5 C -0.07675(18) 0.0036(2) 0.11733(17) 0.0339(7) Uani 1 1 d . . . C6 C 0.00261(17) 0.0191(2) 0.14050(17) 0.0326(7) Uani 1 1 d . . . H6 H 0.0240 -0.0172 0.1819 0.039 Uiso 1 1 calc R . . C7 C 0.13739(17) 0.1035(2) 0.12647(18) 0.0318(7) Uani 1 1 d . . . C8 C -0.09735(18) 0.1943(2) -0.04504(16) 0.0296(6) Uani 1 1 d . . . C9 C -0.0956(2) -0.1340(3) 0.2044(2) 0.0612(11) Uani 1 1 d . . . H9A H -0.0488 -0.1666 0.1828 0.092 Uiso 1 1 calc R . . H9B H -0.1357 -0.1837 0.2174 0.092 Uiso 1 1 calc R . . H9C H -0.0802 -0.0980 0.2504 0.092 Uiso 1 1 calc R . . C10 C 0.31040(18) 0.3361(2) 0.25321(18) 0.0342(7) Uani 1 1 d . . . H10 H 0.3213 0.3905 0.2209 0.041 Uiso 1 1 calc R . . C11 C 0.2833(2) 0.1887(3) 0.29400(19) 0.0517(10) Uani 1 1 d . . . H11 H 0.2716 0.1203 0.2948 0.062 Uiso 1 1 calc R . . C12 C 0.2901(2) 0.2468(3) 0.35699(19) 0.0504(9) Uani 1 1 d . . . H12 H 0.2843 0.2269 0.4085 0.060 Uiso 1 1 calc R . . C13 C 0.31793(18) 0.4312(3) 0.3790(2) 0.0427(8) Uani 1 1 d . . . H13A H 0.3060 0.4141 0.4326 0.051 Uiso 1 1 calc R . . H13B H 0.2789 0.4816 0.3627 0.051 Uiso 1 1 calc R . . C14 C 0.4024(2) 0.4764(3) 0.3751(2) 0.0499(9) Uani 1 1 d . . . H14A H 0.4134 0.4974 0.3221 0.060 Uiso 1 1 calc R . . H14B H 0.4043 0.5358 0.4078 0.060 Uiso 1 1 calc R . . C15 C 0.4665(2) 0.4054(3) 0.4002(2) 0.0557(10) Uani 1 1 d . . . H15A H 0.4539 0.3817 0.4521 0.067 Uiso 1 1 calc R . . H15B H 0.4663 0.3476 0.3658 0.067 Uiso 1 1 calc R . . C16 C 0.56913(18) 0.5462(2) 0.3859(2) 0.0413(8) Uani 1 1 d . . . H16 H 0.5324 0.5965 0.3727 0.050 Uiso 1 1 calc R . . C17 C 0.67886(19) 0.4671(2) 0.41272(18) 0.0372(7) Uani 1 1 d . . . H17 H 0.7334 0.4534 0.4218 0.045 Uiso 1 1 calc R . . C18 C 0.61857(19) 0.3993(2) 0.41696(19) 0.0408(8) Uani 1 1 d . . . H18 H 0.6234 0.3313 0.4288 0.049 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 0.02213(18) 0.03052(19) 0.03008(19) 0.00148(14) -0.00159(14) 0.00078(14) O1 0.0328(12) 0.0502(14) 0.0546(15) 0.0175(12) -0.0142(11) -0.0021(11) O2 0.0234(11) 0.0394(12) 0.0503(13) 0.0087(10) -0.0075(10) -0.0047(9) O3 0.0365(13) 0.0466(13) 0.0556(14) 0.0196(12) 0.0039(11) 0.0045(11) O4 0.0259(11) 0.0443(13) 0.0365(11) 0.0049(10) -0.0059(9) 0.0047(9) O5 0.0296(12) 0.0684(16) 0.0639(16) 0.0333(13) -0.0046(11) -0.0147(12) N1 0.0361(14) 0.0310(13) 0.0294(13) 0.0020(10) -0.0014(11) -0.0012(11) N2 0.0267(13) 0.0380(14) 0.0346(14) -0.0052(11) -0.0045(11) -0.0003(11) N3 0.0294(14) 0.0293(14) 0.0616(18) -0.0037(13) 0.0000(12) -0.0052(11) N4 0.0248(13) 0.0288(13) 0.0454(16) -0.0011(11) -0.0024(11) 0.0002(10) C1 0.0213(14) 0.0264(15) 0.0352(16) -0.0023(12) -0.0020(12) 0.0007(11) C2 0.0243(15) 0.0255(14) 0.0367(16) 0.0000(12) -0.0002(13) -0.0015(12) C3 0.0257(15) 0.0271(15) 0.0298(15) -0.0018(12) -0.0023(12) 0.0033(12) C4 0.0205(14) 0.0397(17) 0.0382(17) 0.0009(14) -0.0034(13) -0.0008(13) C5 0.0264(15) 0.0396(17) 0.0357(16) 0.0051(14) 0.0037(13) -0.0038(13) C6 0.0286(16) 0.0366(17) 0.0326(16) 0.0044(13) -0.0029(13) 0.0011(13) C7 0.0249(15) 0.0273(15) 0.0431(18) -0.0004(14) -0.0051(14) 0.0014(12) C8 0.0312(16) 0.0262(14) 0.0315(15) -0.0043(13) -0.0022(13) 0.0013(13) C9 0.048(2) 0.072(3) 0.064(2) 0.031(2) 0.0026(19) -0.009(2) C10 0.0330(17) 0.0361(17) 0.0334(16) 0.0030(13) 0.0004(13) -0.0047(13) C11 0.087(3) 0.0314(17) 0.0370(18) 0.0076(15) -0.0085(18) -0.0062(18) C12 0.076(3) 0.045(2) 0.0304(17) 0.0088(15) -0.0071(17) -0.0028(19) C13 0.0307(16) 0.051(2) 0.0466(19) -0.0166(16) -0.0022(15) -0.0003(15) C14 0.0374(19) 0.054(2) 0.059(2) -0.0189(18) -0.0047(17) -0.0017(16) C15 0.044(2) 0.043(2) 0.080(3) 0.0027(19) -0.0059(19) -0.0124(17) C16 0.0281(17) 0.0321(17) 0.064(2) -0.0018(16) -0.0034(16) 0.0001(13) C17 0.0295(16) 0.0377(18) 0.0443(19) -0.0007(15) -0.0006(14) 0.0048(14) C18 0.0384(19) 0.0297(16) 0.054(2) 0.0016(15) 0.0022(16) 0.0025(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 1.964(2) . ? Zn1 O4 1.979(2) 4 ? Zn1 N1 1.997(2) . ? Zn1 N4 2.022(2) 3_645 ? O1 C7 1.232(3) . ? O2 C7 1.285(3) . ? O3 C8 1.232(3) . ? O4 C8 1.286(3) . ? O4 Zn1 1.979(2) 4_455 ? O5 C5 1.374(3) . ? O5 C9 1.411(4) . ? N1 C10 1.318(4) . ? N1 C11 1.359(4) . ? N2 C10 1.338(4) . ? N2 C12 1.359(4) . ? N2 C13 1.469(4) . ? N3 C16 1.341(4) . ? N3 C18 1.369(4) . ? N3 C15 1.478(4) . ? N4 C16 1.316(4) . ? N4 C17 1.377(4) . ? N4 Zn1 2.022(2) 3_655 ? C1 C2 1.382(4) . ? C1 C6 1.398(4) . ? C1 C7 1.505(4) . ? C2 C3 1.396(4) . ? C2 H2 0.9300 . ? C3 C4 1.380(4) . ? C3 C8 1.500(4) . ? C4 C5 1.387(4) . ? C4 H4 0.9300 . ? C5 C6 1.382(4) . ? C6 H6 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10 0.9300 . ? C11 C12 1.336(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.518(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.481(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16 0.9300 . ? C17 C18 1.343(4) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Zn1 O4 100.86(9) . 4 ? O2 Zn1 N1 112.61(10) . . ? O4 Zn1 N1 109.97(9) 4 . ? O2 Zn1 N4 106.80(9) . 3_645 ? O4 Zn1 N4 113.16(9) 4 3_645 ? N1 Zn1 N4 112.83(10) . 3_645 ? C7 O2 Zn1 116.30(18) . . ? C8 O4 Zn1 111.28(18) . 4_455 ? C5 O5 C9 117.9(2) . . ? C10 N1 C11 105.2(3) . . ? C10 N1 Zn1 129.6(2) . . ? C11 N1 Zn1 125.1(2) . . ? C10 N2 C12 107.2(3) . . ? C10 N2 C13 126.8(3) . . ? C12 N2 C13 126.1(3) . . ? C16 N3 C18 107.3(3) . . ? C16 N3 C15 127.9(3) . . ? C18 N3 C15 124.8(3) . . ? C16 N4 C17 105.3(3) . . ? C16 N4 Zn1 126.9(2) . 3_655 ? C17 N4 Zn1 127.8(2) . 3_655 ? C2 C1 C6 119.8(3) . . ? C2 C1 C7 121.3(3) . . ? C6 C1 C7 118.9(3) . . ? C1 C2 C3 120.4(3) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 119.3(3) . . ? C4 C3 C8 121.5(2) . . ? C2 C3 C8 119.2(3) . . ? C3 C4 C5 120.6(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? O5 C5 C6 124.5(3) . . ? O5 C5 C4 115.4(3) . . ? C6 C5 C4 120.1(3) . . ? C5 C6 C1 119.7(3) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? O1 C7 O2 124.1(3) . . ? O1 C7 C1 120.3(3) . . ? O2 C7 C1 115.5(3) . . ? O3 C8 O4 123.4(3) . . ? O3 C8 C3 120.1(3) . . ? O4 C8 C3 116.5(3) . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 N2 111.0(3) . . ? N1 C10 H10 124.5 . . ? N2 C10 H10 124.5 . . ? C12 C11 N1 110.4(3) . . ? C12 C11 H11 124.8 . . ? N1 C11 H11 124.8 . . ? C11 C12 N2 106.2(3) . . ? C11 C12 H12 126.9 . . ? N2 C12 H12 126.9 . . ? N2 C13 C14 114.1(3) . . ? N2 C13 H13A 108.7 . . ? C14 C13 H13A 108.7 . . ? N2 C13 H13B 108.7 . . ? C14 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C15 C14 C13 112.8(3) . . ? C15 C14 H14A 109.0 . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14B 109.0 . . ? C13 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? N3 C15 C14 113.2(3) . . ? N3 C15 H15A 108.9 . . ? C14 C15 H15A 108.9 . . ? N3 C15 H15B 108.9 . . ? C14 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? N4 C16 N3 111.3(3) . . ? N4 C16 H16 124.4 . . ? N3 C16 H16 124.4 . . ? C18 C17 N4 109.9(3) . . ? C18 C17 H17 125.0 . . ? N4 C17 H17 125.0 . . ? C17 C18 N3 106.2(3) . . ? C17 C18 H18 126.9 . . ? N3 C18 H18 126.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Zn1 O2 C7 -175.8(2) 4 . . . ? N1 Zn1 O2 C7 -58.7(2) . . . . ? N4 Zn1 O2 C7 65.7(2) 3_645 . . . ? O2 Zn1 N1 C10 -104.4(3) . . . . ? O4 Zn1 N1 C10 7.3(3) 4 . . . ? N4 Zn1 N1 C10 134.6(3) 3_645 . . . ? O2 Zn1 N1 C11 74.3(3) . . . . ? O4 Zn1 N1 C11 -174.1(3) 4 . . . ? N4 Zn1 N1 C11 -46.8(3) 3_645 . . . ? C6 C1 C2 C3 2.1(4) . . . . ? C7 C1 C2 C3 -178.9(3) . . . . ? C1 C2 C3 C4 -2.2(4) . . . . ? C1 C2 C3 C8 176.3(3) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C8 C3 C4 C5 -178.6(3) . . . . ? C9 O5 C5 C6 -7.0(5) . . . . ? C9 O5 C5 C4 172.9(3) . . . . ? C3 C4 C5 O5 -177.4(3) . . . . ? C3 C4 C5 C6 2.6(5) . . . . ? O5 C5 C6 C1 177.3(3) . . . . ? C4 C5 C6 C1 -2.6(5) . . . . ? C2 C1 C6 C5 0.2(4) . . . . ? C7 C1 C6 C5 -178.7(3) . . . . ? Zn1 O2 C7 O1 -3.3(4) . . . . ? Zn1 O2 C7 C1 177.03(18) . . . . ? C2 C1 C7 O1 178.1(3) . . . . ? C6 C1 C7 O1 -3.0(4) . . . . ? C2 C1 C7 O2 -2.2(4) . . . . ? C6 C1 C7 O2 176.7(3) . . . . ? Zn1 O4 C8 O3 -8.2(4) 4_455 . . . ? Zn1 O4 C8 C3 169.60(18) 4_455 . . . ? C4 C3 C8 O3 -161.7(3) . . . . ? C2 C3 C8 O3 19.9(4) . . . . ? C4 C3 C8 O4 20.5(4) . . . . ? C2 C3 C8 O4 -157.9(3) . . . . ? C11 N1 C10 N2 0.0(4) . . . . ? Zn1 N1 C10 N2 178.87(19) . . . . ? C12 N2 C10 N1 0.1(4) . . . . ? C13 N2 C10 N1 -178.4(3) . . . . ? C10 N1 C11 C12 -0.2(4) . . . . ? Zn1 N1 C11 C12 -179.1(2) . . . . ? N1 C11 C12 N2 0.3(4) . . . . ? C10 N2 C12 C11 -0.3(4) . . . . ? C13 N2 C12 C11 178.3(3) . . . . ? C10 N2 C13 C14 -65.2(4) . . . . ? C12 N2 C13 C14 116.4(4) . . . . ? N2 C13 C14 C15 -59.4(4) . . . . ? C16 N3 C15 C14 4.7(5) . . . . ? C18 N3 C15 C14 -176.1(3) . . . . ? C13 C14 C15 N3 -177.0(3) . . . . ? C17 N4 C16 N3 0.1(4) . . . . ? Zn1 N4 C16 N3 -178.4(2) 3_655 . . . ? C18 N3 C16 N4 -0.5(4) . . . . ? C15 N3 C16 N4 178.7(3) . . . . ? C16 N4 C17 C18 0.4(4) . . . . ? Zn1 N4 C17 C18 178.9(2) 3_655 . . . ? N4 C17 C18 N3 -0.7(4) . . . . ? C16 N3 C18 C17 0.7(4) . . . . ? C15 N3 C18 C17 -178.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.596 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.061 # Attachment '- 5.cif' data_a_5 _database_code_depnum_ccdc_archive 'CCDC 762926' #TrackingRef '- 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 N4 O5 Zn' _chemical_formula_weight 477.81 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7754(10) _cell_length_b 10.1743(11) _cell_length_c 11.4600(12) _cell_angle_alpha 94.8700(10) _cell_angle_beta 100.6930(10) _cell_angle_gamma 105.2020(10) _cell_volume 1070.03(19) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3375 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 1.188 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7717 _exptl_absorpt_correction_T_max 0.8513 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8191 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3951 _reflns_number_gt 3465 _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^)+(0.0412P)^2^+0.3994P] 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 3951 _refine_ls_number_parameters 309 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0791 _refine_ls_wR_factor_gt 0.0747 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.027 _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 C20 C -0.1944(5) 0.0355(7) -0.0204(6) 0.060(2) Uani 0.581(5) 1 d PD A 1 H20A H -0.1755 -0.0467 0.0078 0.072 Uiso 0.581(5) 1 calc PR A 1 H20B H -0.2015 0.0263 -0.1064 0.072 Uiso 0.581(5) 1 calc PR A 1 C21 C -0.3398(5) 0.0508(6) 0.0084(8) 0.100(3) Uani 0.581(5) 1 d PD A 1 H21A H -0.3266 0.0805 0.0934 0.120 Uiso 0.581(5) 1 calc PR A 1 H21B H -0.3710 0.1190 -0.0356 0.120 Uiso 0.581(5) 1 calc PR A 1 C22 C -0.4511(5) -0.0861(6) -0.0278(6) 0.088(2) Uani 0.581(5) 1 d PD A 1 H22A H -0.4455 -0.1252 -0.1054 0.132 Uiso 0.581(5) 1 d PR A 1 H22C H -0.4314 -0.1454 0.0300 0.132 Uiso 0.581(5) 1 d PR A 1 C20' C -0.1851(7) 0.0204(8) 0.0055(10) 0.055(3) Uani 0.419(5) 1 d PD A 2 H20C H -0.2008 -0.0053 -0.0804 0.066 Uiso 0.419(5) 1 calc PR A 2 H20D H -0.1440 -0.0463 0.0439 0.066 Uiso 0.419(5) 1 calc PR A 2 C21' C -0.3250(6) 0.0076(7) 0.0351(7) 0.060(2) Uani 0.419(5) 1 d PD A 2 H21C H -0.3108 0.0234 0.1217 0.072 Uiso 0.419(5) 1 calc PR A 2 H21D H -0.3847 -0.0864 0.0082 0.072 Uiso 0.419(5) 1 calc PR A 2 C22' C -0.4056(7) 0.0999(7) -0.0154(6) 0.069(2) Uani 0.419(5) 1 d PD A 2 H22D H -0.3552 0.1929 0.0203 0.103 Uiso 0.419(5) 1 d PR A 2 H22F H -0.4109 0.0915 -0.1003 0.103 Uiso 0.419(5) 1 d PR A 2 Zn1 Zn 0.26144(2) 0.38685(2) 0.31687(2) 0.03287(7) Uani 1 1 d . . . O1 O 0.40523(15) 0.27758(13) 0.32978(13) 0.0400(4) Uani 1 1 d . . . O2 O 0.20852(15) 0.12046(14) 0.34898(14) 0.0446(4) Uani 1 1 d . . . O3 O 0.19368(15) -0.36899(14) 0.25855(14) 0.0448(4) Uani 1 1 d . . . O4 O 0.39554(15) -0.42865(13) 0.31872(14) 0.0400(4) Uani 1 1 d . . . O5 O 0.78895(16) 0.03203(15) 0.36435(16) 0.0515(4) Uani 1 1 d . . . N1 N 0.19330(18) 0.41149(16) 0.46905(15) 0.0361(4) Uani 1 1 d . . . N2 N 0.2099(2) 0.4872(2) 0.65756(17) 0.0488(5) Uani 1 1 d . . . N3 N 0.1039(2) 0.30737(18) 0.16813(16) 0.0429(4) Uani 1 1 d . A . N4 N -0.0744(2) 0.1575(2) 0.03899(17) 0.0506(5) Uani 1 1 d D . . C1 C 0.4202(2) 0.04900(18) 0.34418(16) 0.0303(4) Uani 1 1 d . . . C2 C 0.3424(2) -0.08917(18) 0.32689(17) 0.0310(4) Uani 1 1 d . . . H2 H 0.2421 -0.1142 0.3183 0.037 Uiso 1 1 calc R . . C3 C 0.4141(2) -0.19008(18) 0.32246(16) 0.0290(4) Uani 1 1 d . . . C4 C 0.5645(2) -0.15345(19) 0.33763(18) 0.0340(4) Uani 1 1 d . . . H4 H 0.6129 -0.2209 0.3372 0.041 Uiso 1 1 calc R . . C5 C 0.6419(2) -0.0148(2) 0.35356(18) 0.0347(5) Uani 1 1 d . . . C6 C 0.5692(2) 0.08542(19) 0.35674(18) 0.0350(5) Uani 1 1 d . . . H6 H 0.6213 0.1779 0.3674 0.042 Uiso 1 1 calc R . . C7 C 0.3372(2) 0.15540(19) 0.34221(17) 0.0334(5) Uani 1 1 d . . . C8 C 0.3263(2) -0.33955(19) 0.29763(17) 0.0317(4) Uani 1 1 d . . . C9 C 0.8662(2) -0.0684(2) 0.3642(3) 0.0551(7) Uani 1 1 d . . . H9A H 0.8500 -0.1214 0.4283 0.083 Uiso 1 1 calc R . . H9B H 0.9681 -0.0234 0.3752 0.083 Uiso 1 1 calc R . . H9C H 0.8328 -0.1281 0.2890 0.083 Uiso 1 1 calc R . . C10 C 0.2777(2) 0.4923(2) 0.56574(19) 0.0430(5) Uani 1 1 d . . . H10 H 0.3720 0.5459 0.5698 0.052 Uiso 1 1 calc R . . C11 C 0.0651(2) 0.3518(2) 0.5016(2) 0.0460(6) Uani 1 1 d . . . H11 H -0.0157 0.2894 0.4513 0.055 Uiso 1 1 calc R . . C12 C 0.0745(3) 0.3976(3) 0.6172(2) 0.0516(6) Uani 1 1 d . . . H12 H 0.0029 0.3731 0.6610 0.062 Uiso 1 1 calc R . . C13 C 0.2794(3) 0.5543(3) 0.7806(2) 0.0652(7) Uani 1 1 d . . . H13A H 0.2065 0.5741 0.8206 0.078 Uiso 1 1 calc R . . H13B H 0.3494 0.6410 0.7783 0.078 Uiso 1 1 calc R . . C14 C 0.3553(3) 0.4654(3) 0.8513(2) 0.0637(7) Uani 1 1 d . . . H14A H 0.4099 0.4269 0.8020 0.076 Uiso 1 1 calc R . . H14B H 0.2829 0.3895 0.8701 0.076 Uiso 1 1 calc R . . C15 C 0.4575(3) 0.5432(3) 0.9670(2) 0.0717(8) Uani 1 1 d . . . H15A H 0.4017 0.5754 1.0190 0.086 Uiso 1 1 calc R . . H15B H 0.5251 0.6233 0.9489 0.086 Uiso 1 1 calc R . . C17 C 0.0122(3) 0.1829(2) 0.1481(2) 0.0480(6) Uani 1 1 d . A . H17 H 0.0083 0.1205 0.2031 0.058 Uiso 1 1 calc R . . C18 C 0.0717(3) 0.3639(3) 0.0656(2) 0.0568(7) Uani 1 1 d . . . H18 H 0.1179 0.4523 0.0533 0.068 Uiso 1 1 calc R A . C19 C -0.0374(3) 0.2719(3) -0.0147(2) 0.0597(7) Uani 1 1 d . A . H19 H -0.0788 0.2844 -0.0914 0.072 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 C20 0.043(3) 0.074(4) 0.047(3) 0.009(3) -0.011(2) 0.004(3) C21 0.056(3) 0.077(4) 0.164(7) 0.043(4) -0.017(4) 0.034(3) C22 0.064(3) 0.090(4) 0.096(4) -0.008(3) 0.027(3) -0.003(3) C20' 0.045(4) 0.056(5) 0.045(5) -0.007(4) -0.021(3) 0.008(3) C21' 0.045(4) 0.058(5) 0.065(4) -0.003(4) -0.008(3) 0.009(3) C22' 0.075(5) 0.059(4) 0.066(4) 0.009(3) 0.013(4) 0.009(4) Zn1 0.03591(13) 0.02128(11) 0.04094(13) 0.00495(9) 0.00427(10) 0.00993(9) O1 0.0411(8) 0.0195(6) 0.0597(9) 0.0079(6) 0.0075(7) 0.0109(6) O2 0.0361(8) 0.0316(7) 0.0683(10) 0.0097(7) 0.0094(7) 0.0141(6) O3 0.0360(8) 0.0275(7) 0.0661(10) 0.0048(7) 0.0045(7) 0.0058(6) O4 0.0387(8) 0.0197(6) 0.0642(9) 0.0097(6) 0.0129(7) 0.0104(6) O5 0.0315(8) 0.0324(8) 0.0909(12) 0.0173(8) 0.0098(8) 0.0094(6) N1 0.0351(9) 0.0292(8) 0.0448(10) 0.0069(7) 0.0078(8) 0.0106(7) N2 0.0591(12) 0.0508(11) 0.0446(10) 0.0094(9) 0.0178(9) 0.0240(10) N3 0.0480(10) 0.0337(9) 0.0429(10) 0.0066(8) -0.0020(8) 0.0125(8) N4 0.0435(11) 0.0530(12) 0.0478(11) 0.0003(9) -0.0036(9) 0.0123(9) C1 0.0358(10) 0.0232(9) 0.0321(10) 0.0043(7) 0.0031(8) 0.0116(8) C2 0.0317(10) 0.0252(9) 0.0366(10) 0.0052(8) 0.0051(8) 0.0101(8) C3 0.0351(10) 0.0201(9) 0.0322(10) 0.0050(7) 0.0067(8) 0.0083(8) C4 0.0355(10) 0.0255(9) 0.0451(11) 0.0079(8) 0.0096(9) 0.0142(8) C5 0.0296(10) 0.0283(10) 0.0457(11) 0.0094(8) 0.0057(9) 0.0074(8) C6 0.0372(11) 0.0195(9) 0.0445(11) 0.0055(8) 0.0018(9) 0.0061(8) C7 0.0401(11) 0.0223(9) 0.0365(10) 0.0024(8) 0.0008(9) 0.0125(8) C8 0.0375(11) 0.0223(9) 0.0378(10) 0.0065(8) 0.0128(9) 0.0091(8) C9 0.0346(12) 0.0466(13) 0.0894(18) 0.0197(12) 0.0140(12) 0.0172(10) C10 0.0415(12) 0.0408(12) 0.0453(12) 0.0038(10) 0.0100(10) 0.0093(10) C11 0.0354(11) 0.0396(12) 0.0649(15) 0.0162(11) 0.0093(10) 0.0121(9) C12 0.0456(13) 0.0557(14) 0.0679(15) 0.0259(12) 0.0261(11) 0.0242(11) C13 0.0902(19) 0.0680(17) 0.0455(14) 0.0029(12) 0.0176(13) 0.0357(15) C14 0.0799(18) 0.0737(18) 0.0442(14) 0.0044(12) 0.0145(13) 0.0336(15) C15 0.093(2) 0.079(2) 0.0501(15) 0.0043(13) 0.0133(14) 0.0394(17) C17 0.0494(13) 0.0411(12) 0.0454(13) 0.0063(10) -0.0036(11) 0.0087(10) C18 0.0693(17) 0.0450(13) 0.0510(14) 0.0149(11) -0.0010(12) 0.0148(12) C19 0.0692(17) 0.0621(16) 0.0444(13) 0.0096(12) -0.0047(12) 0.0242(14) _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 C20 N4 1.475(5) . ? C20 C21 1.561(7) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.495(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22C 0.9600 . ? C20' C21' 1.445(10) . ? C20' N4 1.493(7) . ? C20' H20C 0.9700 . ? C20' H20D 0.9700 . ? C21' C22' 1.466(7) . ? C21' H21C 0.9700 . ? C21' H21D 0.9700 . ? C22' H22D 0.9600 . ? C22' H22F 0.9600 . ? Zn1 O4 1.9837(13) 1_565 ? Zn1 N1 1.9982(17) . ? Zn1 O1 2.0009(14) . ? Zn1 N3 2.0174(17) . ? O1 C7 1.280(2) . ? O2 C7 1.233(2) . ? O3 C8 1.237(2) . ? O4 C8 1.279(2) . ? O4 Zn1 1.9837(13) 1_545 ? O5 C5 1.369(2) . ? O5 C9 1.421(3) . ? N1 C10 1.317(3) . ? N1 C11 1.375(3) . ? N2 C10 1.341(3) . ? N2 C12 1.365(3) . ? N2 C13 1.468(3) . ? N3 C17 1.319(3) . ? N3 C18 1.373(3) . ? N4 C17 1.336(3) . ? N4 C19 1.360(3) . ? C1 C6 1.382(3) . ? C1 C2 1.389(3) . ? C1 C7 1.513(3) . ? C2 C3 1.390(3) . ? C2 H2 0.9300 . ? C3 C4 1.391(3) . ? C3 C8 1.511(2) . ? C4 C5 1.394(3) . ? C4 H4 0.9300 . ? C5 C6 1.389(3) . ? C6 H6 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10 0.9300 . ? C11 C12 1.345(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.510(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.516(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C15 1.517(6) 2_667 ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C17 H17 0.9300 . ? C18 C19 1.352(3) . ? C18 H18 0.9300 . ? C19 H19 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 N4 C20 C21 109.5(5) . . ? N4 C20 H20A 109.8 . . ? C21 C20 H20A 109.8 . . ? N4 C20 H20B 109.8 . . ? C21 C20 H20B 109.8 . . ? H20A C20 H20B 108.2 . . ? C22 C21 C20 108.0(5) . . ? C22 C21 H21A 110.1 . . ? C20 C21 H21A 110.1 . . ? C22 C21 H21B 110.1 . . ? C20 C21 H21B 110.1 . . ? H21A C21 H21B 108.4 . . ? C22 C21 H22D 131.1 . . ? C20 C21 H22D 116.4 . . ? H21A C21 H22D 73.3 . . ? H21B C21 H22D 36.0 . . ? C22 C21 H22F 86.8 . . ? C20 C21 H22F 103.8 . . ? H21A C21 H22F 134.2 . . ? H21B C21 H22F 28.6 . . ? H22D C21 H22F 64.3 . . ? C21 C22 H22A 109.3 . . ? C21 C22 H22C 108.7 . . ? H22A C22 H22C 109.5 . . ? C21' C20' N4 117.6(6) . . ? C21' C20' H20C 107.9 . . ? N4 C20' H20C 107.9 . . ? C21' C20' H20D 107.9 . . ? N4 C20' H20D 107.9 . . ? H20C C20' H20D 107.2 . . ? C20' C21' C22' 116.3(7) . . ? C20' C21' H21C 108.2 . . ? C22' C21' H21C 108.2 . . ? C20' C21' H21D 108.2 . . ? C22' C21' H21D 108.2 . . ? H21C C21' H21D 107.4 . . ? C21' C22' H22D 109.3 . . ? C21' C22' H22F 108.4 . . ? H22D C22' H22F 109.5 . . ? O4 Zn1 N1 102.00(6) 1_565 . ? O4 Zn1 O1 98.90(6) 1_565 . ? N1 Zn1 O1 112.32(6) . . ? O4 Zn1 N3 117.43(7) 1_565 . ? N1 Zn1 N3 115.66(7) . . ? O1 Zn1 N3 109.28(7) . . ? C7 O1 Zn1 106.84(12) . . ? C8 O4 Zn1 111.48(12) . 1_545 ? C5 O5 C9 117.04(16) . . ? C10 N1 C11 105.61(19) . . ? C10 N1 Zn1 122.21(15) . . ? C11 N1 Zn1 132.11(15) . . ? C10 N2 C12 107.21(19) . . ? C10 N2 C13 124.4(2) . . ? C12 N2 C13 128.0(2) . . ? C17 N3 C18 105.06(19) . . ? C17 N3 Zn1 125.53(15) . . ? C18 N3 Zn1 129.35(16) . . ? C17 N4 C19 107.4(2) . . ? C17 N4 C20 130.6(4) . . ? C19 N4 C20 121.9(3) . . ? C17 N4 C20' 117.0(5) . . ? C19 N4 C20' 135.6(5) . . ? C20 N4 C20' 13.7(6) . . ? C6 C1 C2 119.63(18) . . ? C6 C1 C7 121.85(17) . . ? C2 C1 C7 118.44(17) . . ? C1 C2 C3 120.13(18) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C2 C3 C4 120.27(17) . . ? C2 C3 C8 119.06(17) . . ? C4 C3 C8 120.65(17) . . ? C3 C4 C5 119.37(18) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? O5 C5 C6 115.98(17) . . ? O5 C5 C4 124.02(18) . . ? C6 C5 C4 119.98(18) . . ? C1 C6 C5 120.59(17) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? O2 C7 O1 123.56(18) . . ? O2 C7 C1 119.33(17) . . ? O1 C7 C1 117.07(18) . . ? O3 C8 O4 123.93(17) . . ? O3 C8 C3 119.04(17) . . ? O4 C8 C3 117.02(17) . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 N2 111.1(2) . . ? N1 C10 H10 124.4 . . ? N2 C10 H10 124.4 . . ? C12 C11 N1 109.5(2) . . ? C12 C11 H11 125.2 . . ? N1 C11 H11 125.2 . . ? C11 C12 N2 106.5(2) . . ? C11 C12 H12 126.7 . . ? N2 C12 H12 126.7 . . ? N2 C13 C14 111.8(2) . . ? N2 C13 H13A 109.3 . . ? C14 C13 H13A 109.3 . . ? N2 C13 H13B 109.3 . . ? C14 C13 H13B 109.3 . . ? H13A C13 H13B 107.9 . . ? C13 C14 C15 113.0(2) . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? C13 C14 H14B 109.0 . . ? C15 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C14 C15 C15 113.0(3) . 2_667 ? C14 C15 H15A 109.0 . . ? C15 C15 H15A 109.0 2_667 . ? C14 C15 H15B 109.0 . . ? C15 C15 H15B 109.0 2_667 . ? H15A C15 H15B 107.8 . . ? N3 C17 N4 111.6(2) . . ? N3 C17 H17 124.2 . . ? N4 C17 H17 124.2 . . ? C19 C18 N3 109.8(2) . . ? C19 C18 H18 125.1 . . ? N3 C18 H18 125.1 . . ? C18 C19 N4 106.2(2) . . ? C18 C19 H19 126.9 . . ? N4 C19 H19 126.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C20 C21 C22 -166.8(5) . . . . ? N4 C20' C21' C22' 58.1(11) . . . . ? O4 Zn1 O1 C7 173.49(13) 1_565 . . . ? N1 Zn1 O1 C7 66.53(14) . . . . ? N3 Zn1 O1 C7 -63.23(14) . . . . ? O4 Zn1 N1 C10 -33.71(17) 1_565 . . . ? O1 Zn1 N1 C10 71.25(17) . . . . ? N3 Zn1 N1 C10 -162.36(16) . . . . ? O4 Zn1 N1 C11 149.92(18) 1_565 . . . ? O1 Zn1 N1 C11 -105.11(19) . . . . ? N3 Zn1 N1 C11 21.3(2) . . . . ? O4 Zn1 N3 C17 174.97(18) 1_565 . . . ? N1 Zn1 N3 C17 -64.4(2) . . . . ? O1 Zn1 N3 C17 63.5(2) . . . . ? O4 Zn1 N3 C18 -1.7(2) 1_565 . . . ? N1 Zn1 N3 C18 118.9(2) . . . . ? O1 Zn1 N3 C18 -113.2(2) . . . . ? C21 C20 N4 C17 89.3(6) . . . . ? C21 C20 N4 C19 -88.3(6) . . . . ? C21 C20 N4 C20' 93(2) . . . . ? C21' C20' N4 C17 88.9(8) . . . . ? C21' C20' N4 C19 -89.6(10) . . . . ? C21' C20' N4 C20 -88(2) . . . . ? C6 C1 C2 C3 0.1(3) . . . . ? C7 C1 C2 C3 176.97(17) . . . . ? C1 C2 C3 C4 1.3(3) . . . . ? C1 C2 C3 C8 -177.09(17) . . . . ? C2 C3 C4 C5 -2.0(3) . . . . ? C8 C3 C4 C5 176.33(18) . . . . ? C9 O5 C5 C6 178.6(2) . . . . ? C9 O5 C5 C4 -2.8(3) . . . . ? C3 C4 C5 O5 -177.23(19) . . . . ? C3 C4 C5 C6 1.4(3) . . . . ? C2 C1 C6 C5 -0.7(3) . . . . ? C7 C1 C6 C5 -177.48(18) . . . . ? O5 C5 C6 C1 178.69(18) . . . . ? C4 C5 C6 C1 0.0(3) . . . . ? Zn1 O1 C7 O2 -2.5(2) . . . . ? Zn1 O1 C7 C1 175.30(13) . . . . ? C6 C1 C7 O2 -169.17(19) . . . . ? C2 C1 C7 O2 14.0(3) . . . . ? C6 C1 C7 O1 12.9(3) . . . . ? C2 C1 C7 O1 -163.91(18) . . . . ? Zn1 O4 C8 O3 -13.0(3) 1_545 . . . ? Zn1 O4 C8 C3 167.14(13) 1_545 . . . ? C2 C3 C8 O3 14.3(3) . . . . ? C4 C3 C8 O3 -164.06(19) . . . . ? C2 C3 C8 O4 -165.81(18) . . . . ? C4 C3 C8 O4 15.8(3) . . . . ? C11 N1 C10 N2 -0.1(2) . . . . ? Zn1 N1 C10 N2 -177.28(14) . . . . ? C12 N2 C10 N1 0.2(3) . . . . ? C13 N2 C10 N1 173.5(2) . . . . ? C10 N1 C11 C12 0.0(2) . . . . ? Zn1 N1 C11 C12 176.77(15) . . . . ? N1 C11 C12 N2 0.1(3) . . . . ? C10 N2 C12 C11 -0.2(3) . . . . ? C13 N2 C12 C11 -173.2(2) . . . . ? C10 N2 C13 C14 -85.4(3) . . . . ? C12 N2 C13 C14 86.5(3) . . . . ? N2 C13 C14 C15 166.1(2) . . . . ? C13 C14 C15 C15 -175.5(3) . . . 2_667 ? C18 N3 C17 N4 0.6(3) . . . . ? Zn1 N3 C17 N4 -176.68(16) . . . . ? C19 N4 C17 N3 -0.3(3) . . . . ? C20 N4 C17 N3 -178.1(4) . . . . ? C20' N4 C17 N3 -179.2(4) . . . . ? C17 N3 C18 C19 -0.8(3) . . . . ? Zn1 N3 C18 C19 176.38(18) . . . . ? N3 C18 C19 N4 0.6(3) . . . . ? C17 N4 C19 C18 -0.2(3) . . . . ? C20 N4 C19 C18 177.8(3) . . . . ? C20' N4 C19 C18 178.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.470 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.049