# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H34 Cl N5 O12 Zn' _chemical_formula_weight 625.33 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' Cl Cl 0.1484 0.1585 '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(3) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' _cell_length_a 9.3837(4) _cell_length_b 9.3837(4) _cell_length_c 30.344(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2671.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6167 _cell_measurement_theta_min 2.5522 _cell_measurement_theta_max 27.5089 _exptl_crystal_description Prism _exptl_crystal_colour White _exptl_crystal_size_max 0.3000 _exptl_crystal_size_mid 0.2000 _exptl_crystal_size_min 0.2000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 1.088 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8914 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 'Mercury70 (2x2 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number 3130 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17082 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0591 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5946 _reflns_number_gt 5013 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _chemical_absolute_configuration unk _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0923P)^2^+1.3414P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.034(19) _refine_ls_number_reflns 5946 _refine_ls_number_parameters 338 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0738 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.1691 _refine_ls_wR_factor_gt 0.1589 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.077 _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 0.66824(6) 0.26032(6) 0.190661(18) 0.03170(16) Uani 1 1 d . . . Cl1 Cl 0.1320(3) -0.2601(3) 0.16372(11) 0.0916(8) Uani 1 1 d . . . C1 C 0.2388(8) 0.2926(12) 0.0371(3) 0.074(3) Uani 1 1 d . . . H1A H 0.2715 0.2969 0.0065 0.089 Uiso 1 1 calc R . . C2 C 0.1597(9) 0.4303(11) 0.0490(6) 0.120(5) Uani 1 1 d . . . H2A H 0.2172 0.4880 0.0687 0.144 Uiso 1 1 calc R . . H2B H 0.1400 0.4851 0.0226 0.144 Uiso 1 1 calc R . . C3 C 0.0225(9) 0.3881(9) 0.0712(3) 0.076(2) Uani 1 1 d . . . H3A H 0.0284 0.4024 0.1028 0.091 Uiso 1 1 calc R . . H3B H -0.0570 0.4429 0.0598 0.091 Uiso 1 1 calc R . . C4 C 0.0063(7) 0.2364(8) 0.0607(2) 0.0486(14) Uani 1 1 d . . . C5 C 0.3630(7) 0.2654(8) 0.0671(2) 0.0526(15) Uani 1 1 d . . . C6 C 0.4042(7) 0.4255(7) 0.1745(3) 0.066(2) Uani 1 1 d . . . H6A H 0.4257 0.4461 0.1439 0.079 Uiso 1 1 calc R . . H6B H 0.3036 0.4434 0.1792 0.079 Uiso 1 1 calc R . . C7 C 0.4855(8) 0.5155(9) 0.2020(3) 0.072(2) Uani 1 1 d U . . H7A H 0.4588 0.4984 0.2324 0.086 Uiso 1 1 calc R . . H7B H 0.4630 0.6139 0.1951 0.086 Uiso 1 1 calc R . . C8 C 0.7189(9) 0.5806(6) 0.1657(2) 0.0565(18) Uani 1 1 d . . . H8A H 0.6844 0.5570 0.1365 0.068 Uiso 1 1 calc R . . H8B H 0.8198 0.5580 0.1666 0.068 Uiso 1 1 calc R . . C9 C 0.7012(8) 0.7409(6) 0.1728(2) 0.0501(16) Uani 1 1 d . . . C10 C 0.7504(7) 0.8054(7) 0.2111(2) 0.0496(15) Uani 1 1 d . . . H10A H 0.7939 0.7522 0.2332 0.060 Uiso 1 1 calc R . . C11 C 0.7330(7) 0.9490(6) 0.2153(2) 0.0462(14) Uani 1 1 d . . . H11A H 0.7688 0.9919 0.2406 0.055 Uiso 1 1 calc R . . C12 C 0.6192(7) 0.9674(6) 0.1493(2) 0.0477(15) Uani 1 1 d . . . H12A H 0.5731 1.0220 0.1281 0.057 Uiso 1 1 calc R . . C13 C 0.6348(9) 0.8222(7) 0.1422(2) 0.0554(16) Uani 1 1 d . . . H13A H 0.5998 0.7810 0.1165 0.066 Uiso 1 1 calc R . . C14 C 0.3505(6) 0.2069(8) 0.2184(2) 0.0516(16) Uani 1 1 d . . . H14A H 0.3766 0.2473 0.2466 0.062 Uiso 1 1 calc R . . H14B H 0.3719 0.1058 0.2193 0.062 Uiso 1 1 calc R . . C15 C 0.1913(6) 0.2263(7) 0.2113(2) 0.0428(13) Uani 1 1 d . . . C16 C 0.1204(7) 0.1507(8) 0.1785(2) 0.0540(17) Uani 1 1 d . . . H16A H 0.1697 0.0887 0.1601 0.065 Uiso 1 1 calc R . . C17 C -0.0271(6) 0.1701(7) 0.1739(2) 0.0469(14) Uani 1 1 d . . . H17A H -0.0745 0.1174 0.1525 0.056 Uiso 1 1 calc R . . C18 C -0.0338(6) 0.3332(6) 0.2294(2) 0.0420(12) Uani 1 1 d . . . H18A H -0.0861 0.3952 0.2470 0.050 Uiso 1 1 calc R . . C19 C 0.1106(6) 0.3219(8) 0.2366(2) 0.0527(15) Uani 1 1 d . . . H19A H 0.1544 0.3775 0.2580 0.063 Uiso 1 1 calc R . . N1 N 0.1250(6) 0.1903(8) 0.0411(2) 0.0645(17) Uani 1 1 d . . . H1B H 0.1331 0.1045 0.0315 0.077 Uiso 1 1 calc R . . N2 N 0.4364(5) 0.2735(5) 0.18399(18) 0.0395(11) Uani 1 1 d . . . H2C H 0.4151 0.2255 0.1588 0.047 Uiso 1 1 calc R . . N3 N 0.6469(5) 0.4927(5) 0.19698(18) 0.0396(11) Uani 1 1 d . . . H3C H 0.6853 0.5150 0.2236 0.048 Uiso 1 1 calc R . . N4 N 0.6686(5) 1.0324(4) 0.18602(18) 0.0388(10) Uani 1 1 d . . . N5 N -0.1024(5) 0.2590(5) 0.19834(16) 0.0376(11) Uani 1 1 d . . . O1 O -0.1002(5) 0.1614(6) 0.06816(17) 0.0590(12) Uani 1 1 d . . . O2 O 0.4632(5) 0.3551(6) 0.06544(16) 0.0596(12) Uani 1 1 d . . . O3 O 0.3649(6) 0.1544(7) 0.0902(2) 0.0767(16) Uani 1 1 d . . . O4 O 0.6876(5) 0.2824(5) 0.11932(15) 0.0418(10) Uani 1 1 d . . . O5 O 0.6547(4) 0.2463(4) 0.26388(16) 0.0418(11) Uani 1 1 d . . . O7 O 0.0400(12) -0.1671(10) 0.1422(4) 0.159(5) Uani 1 1 d . . . O8 O 0.2631(11) -0.1983(15) 0.1726(4) 0.161(5) Uani 1 1 d . . . O9 O 0.0867(16) -0.3537(18) 0.1887(6) 0.214(6) Uani 1 1 d U . . O10 O -0.0990(7) -0.1381(7) 0.05921(19) 0.0774(17) Uani 1 1 d . . . O11 O 0.6432(7) 0.5131(6) 0.29760(19) 0.0778(17) Uani 1 1 d . . . O12 O 0.3072(9) -0.1234(9) 0.0649(3) 0.109(2) Uani 1 1 d . . . O6 O 0.200(3) -0.321(3) 0.1256(10) 0.318(11) Uiso 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 0.0246(3) 0.0246(3) 0.0459(3) 0.0004(2) -0.0009(2) -0.0004(2) Cl1 0.0973(18) 0.0624(13) 0.1149(19) 0.0073(13) -0.0378(15) 0.0179(12) C1 0.047(4) 0.128(8) 0.048(4) 0.021(4) -0.001(3) -0.023(4) C2 0.043(5) 0.075(6) 0.242(15) 0.070(8) -0.003(6) -0.005(4) C3 0.054(5) 0.055(4) 0.118(7) 0.000(4) -0.019(4) 0.003(4) C4 0.036(3) 0.065(4) 0.044(3) -0.007(3) -0.006(2) -0.004(3) C5 0.048(4) 0.058(4) 0.053(4) 0.001(3) 0.003(3) -0.001(3) C6 0.029(3) 0.041(3) 0.127(7) 0.014(4) -0.007(3) 0.003(2) C7 0.045(4) 0.059(4) 0.112(6) -0.020(4) -0.006(4) 0.021(3) C8 0.080(5) 0.027(3) 0.062(4) 0.001(3) 0.027(3) 0.003(3) C9 0.072(4) 0.029(3) 0.049(3) 0.000(2) 0.013(3) -0.005(3) C10 0.059(4) 0.034(3) 0.056(4) 0.007(3) -0.013(3) -0.003(3) C11 0.053(4) 0.031(3) 0.054(3) 0.000(2) -0.014(3) 0.001(2) C12 0.066(4) 0.026(3) 0.052(3) 0.000(2) -0.021(3) -0.003(2) C13 0.076(5) 0.039(3) 0.051(3) 0.002(3) -0.011(3) -0.010(3) C14 0.029(3) 0.064(4) 0.062(4) 0.023(3) -0.002(3) -0.004(3) C15 0.029(3) 0.057(4) 0.042(3) 0.009(3) 0.001(2) 0.002(3) C16 0.030(3) 0.062(4) 0.070(5) -0.008(3) -0.001(3) 0.003(3) C17 0.036(3) 0.048(3) 0.057(3) -0.010(3) -0.006(2) 0.001(2) C18 0.026(2) 0.045(3) 0.055(3) -0.008(3) 0.001(2) -0.009(2) C19 0.029(3) 0.070(5) 0.060(4) -0.007(3) -0.006(3) -0.007(3) N1 0.038(3) 0.091(5) 0.065(4) -0.017(3) 0.005(3) -0.005(3) N2 0.0227(19) 0.036(2) 0.060(3) 0.005(2) 0.004(2) 0.0013(16) N3 0.038(2) 0.025(2) 0.056(3) -0.005(2) -0.002(2) -0.0009(17) N4 0.037(2) 0.025(2) 0.055(3) -0.002(2) -0.006(2) 0.0006(16) N5 0.022(2) 0.044(3) 0.047(3) -0.004(2) -0.0017(18) -0.0036(17) O1 0.045(3) 0.063(3) 0.069(3) -0.014(2) 0.006(2) -0.002(2) O2 0.043(3) 0.071(3) 0.066(3) 0.008(2) -0.007(2) -0.009(2) O3 0.068(4) 0.078(4) 0.084(4) 0.011(3) -0.022(3) -0.010(3) O4 0.037(2) 0.044(2) 0.044(2) 0.0008(18) 0.0004(17) 0.0034(17) O5 0.040(2) 0.038(2) 0.047(3) -0.0024(17) -0.0022(17) 0.0020(16) O7 0.154(9) 0.097(6) 0.224(11) 0.019(7) -0.093(8) 0.039(6) O8 0.091(6) 0.225(13) 0.168(10) 0.083(9) -0.027(6) -0.031(7) O9 0.173(9) 0.216(9) 0.254(9) 0.106(8) 0.005(8) -0.026(7) O10 0.096(5) 0.072(4) 0.064(3) -0.016(3) -0.011(3) -0.002(3) O11 0.091(4) 0.059(3) 0.084(4) -0.021(3) -0.011(3) 0.015(3) O12 0.105(6) 0.106(6) 0.117(6) -0.030(5) 0.010(5) -0.006(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 N4 2.143(4) 1_545 ? Zn1 N5 2.165(4) 1_655 ? Zn1 O4 2.182(5) . ? Zn1 N2 2.189(4) . ? Zn1 N3 2.198(4) . ? Zn1 O5 2.229(5) . ? Cl1 O9 1.235(13) . ? Cl1 O8 1.387(10) . ? Cl1 O7 1.390(8) . ? Cl1 O6 1.44(3) . ? C1 N1 1.441(11) . ? C1 C5 1.500(10) . ? C1 C2 1.533(15) . ? C1 H1A 0.9800 . ? C2 C3 1.507(13) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.466(11) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 O1 1.244(8) . ? C4 N1 1.334(9) . ? C5 O3 1.257(9) . ? C5 O2 1.263(8) . ? C6 C7 1.411(11) . ? C6 N2 1.486(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N3 1.538(9) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N3 1.427(8) . ? C8 C9 1.529(9) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C13 1.354(10) . ? C9 C10 1.388(9) . ? C10 C11 1.364(8) . ? C10 H10A 0.9300 . ? C11 N4 1.330(8) . ? C11 H11A 0.9300 . ? C12 N4 1.351(8) . ? C12 C13 1.387(9) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 N2 1.459(8) . ? C14 C15 1.520(8) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.392(9) . ? C15 C19 1.402(10) . ? C16 C17 1.403(9) . ? C16 H16A 0.9300 . ? C17 N5 1.321(8) . ? C17 H17A 0.9300 . ? C18 N5 1.337(7) . ? C18 C19 1.377(8) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? N1 H1B 0.8600 . ? N2 H2C 0.9100 . ? N3 H3C 0.9100 . ? N4 Zn1 2.143(4) 1_565 ? N5 Zn1 2.165(4) 1_455 ? 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 Zn1 N5 89.99(18) 1_545 1_655 ? N4 Zn1 O4 91.69(19) 1_545 . ? N5 Zn1 O4 91.40(17) 1_655 . ? N4 Zn1 N2 92.97(17) 1_545 . ? N5 Zn1 N2 176.96(19) 1_655 . ? O4 Zn1 N2 89.18(18) . . ? N4 Zn1 N3 174.71(18) 1_545 . ? N5 Zn1 N3 94.98(18) 1_655 . ? O4 Zn1 N3 90.00(18) . . ? N2 Zn1 N3 82.04(17) . . ? N4 Zn1 O5 90.38(19) 1_545 . ? N5 Zn1 O5 87.08(17) 1_655 . ? O4 Zn1 O5 177.4(2) . . ? N2 Zn1 O5 92.23(18) . . ? N3 Zn1 O5 88.07(17) . . ? O9 Cl1 O8 118.9(9) . . ? O9 Cl1 O7 121.4(10) . . ? O8 Cl1 O7 112.3(7) . . ? O9 Cl1 O6 111.3(14) . . ? O8 Cl1 O6 85.8(12) . . ? O7 Cl1 O6 98.5(14) . . ? N1 C1 C5 114.3(7) . . ? N1 C1 C2 100.5(7) . . ? C5 C1 C2 112.2(8) . . ? N1 C1 H1A 109.8 . . ? C5 C1 H1A 109.8 . . ? C2 C1 H1A 109.8 . . ? C3 C2 C1 107.3(7) . . ? C3 C2 H2A 110.3 . . ? C1 C2 H2A 110.3 . . ? C3 C2 H2B 110.3 . . ? C1 C2 H2B 110.3 . . ? H2A C2 H2B 108.5 . . ? C4 C3 C2 104.2(8) . . ? C4 C3 H3A 110.9 . . ? C2 C3 H3A 110.9 . . ? C4 C3 H3B 110.9 . . ? C2 C3 H3B 110.9 . . ? H3A C3 H3B 108.9 . . ? O1 C4 N1 124.7(7) . . ? O1 C4 C3 126.3(7) . . ? N1 C4 C3 109.0(6) . . ? O3 C5 O2 124.4(7) . . ? O3 C5 C1 119.3(7) . . ? O2 C5 C1 116.2(7) . . ? C7 C6 N2 110.5(6) . . ? C7 C6 H6A 109.6 . . ? N2 C6 H6A 109.6 . . ? C7 C6 H6B 109.6 . . ? N2 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C6 C7 N3 113.0(6) . . ? C6 C7 H7A 109.0 . . ? N3 C7 H7A 109.0 . . ? C6 C7 H7B 109.0 . . ? N3 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? N3 C8 C9 115.1(5) . . ? N3 C8 H8A 108.5 . . ? C9 C8 H8A 108.5 . . ? N3 C8 H8B 108.5 . . ? C9 C8 H8B 108.5 . . ? H8A C8 H8B 107.5 . . ? C13 C9 C10 118.7(6) . . ? C13 C9 C8 120.5(6) . . ? C10 C9 C8 120.7(6) . . ? C11 C10 C9 118.0(6) . . ? C11 C10 H10A 121.0 . . ? C9 C10 H10A 121.0 . . ? N4 C11 C10 124.9(6) . . ? N4 C11 H11A 117.5 . . ? C10 C11 H11A 117.5 . . ? N4 C12 C13 122.4(5) . . ? N4 C12 H12A 118.8 . . ? C13 C12 H12A 118.8 . . ? C9 C13 C12 119.7(6) . . ? C9 C13 H13A 120.2 . . ? C12 C13 H13A 120.2 . . ? N2 C14 C15 113.0(5) . . ? N2 C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? N2 C14 H14B 109.0 . . ? C15 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C16 C15 C19 117.3(6) . . ? C16 C15 C14 120.6(6) . . ? C19 C15 C14 122.1(6) . . ? C15 C16 C17 118.5(6) . . ? C15 C16 H16A 120.7 . . ? C17 C16 H16A 120.7 . . ? N5 C17 C16 123.6(6) . . ? N5 C17 H17A 118.2 . . ? C16 C17 H17A 118.2 . . ? N5 C18 C19 123.0(6) . . ? N5 C18 H18A 118.5 . . ? C19 C18 H18A 118.5 . . ? C18 C19 C15 119.7(6) . . ? C18 C19 H19A 120.1 . . ? C15 C19 H19A 120.1 . . ? C4 N1 C1 116.1(7) . . ? C4 N1 H1B 121.9 . . ? C1 N1 H1B 121.9 . . ? C14 N2 C6 116.0(5) . . ? C14 N2 Zn1 117.3(4) . . ? C6 N2 Zn1 105.9(3) . . ? C14 N2 H2C 105.5 . . ? C6 N2 H2C 105.5 . . ? Zn1 N2 H2C 105.5 . . ? C8 N3 C7 116.9(6) . . ? C8 N3 Zn1 118.2(4) . . ? C7 N3 Zn1 103.7(4) . . ? C8 N3 H3C 105.7 . . ? C7 N3 H3C 105.7 . . ? Zn1 N3 H3C 105.7 . . ? C11 N4 C12 116.2(5) . . ? C11 N4 Zn1 122.9(4) . 1_565 ? C12 N4 Zn1 120.3(4) . 1_565 ? C17 N5 C18 117.9(5) . . ? C17 N5 Zn1 118.3(4) . 1_455 ? C18 N5 Zn1 123.4(4) . 1_455 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.669 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.086 _database_code_depnum_ccdc_archive 'CCDC 953111' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H34 Cl N5 O12 Zn' _chemical_formula_weight 625.33 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' Cl Cl 0.1484 0.1585 '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(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+1/4' 'y, -x, z+3/4' _cell_length_a 9.368(3) _cell_length_b 9.368(3) _cell_length_c 30.389(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2667.1(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6294 _cell_measurement_theta_min 2.5542 _cell_measurement_theta_max 27.5477 _exptl_crystal_description Prism _exptl_crystal_colour White _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.2000 _exptl_crystal_size_min 0.2000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 1.090 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8516 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 'Mercury70 (2x2 bin mode)' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17053 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0598 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.52 _reflns_number_total 5612 _reflns_number_gt 4773 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _chemical_absolute_configuration unk _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0866P)^2^+1.2382P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.052(18) _refine_ls_number_reflns 5612 _refine_ls_number_parameters 343 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1619 _refine_ls_wR_factor_gt 0.1512 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.065 _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 0.66822(6) 0.73958(6) -0.086900(16) 0.03147(15) Uani 1 1 d . . . Cl1 Cl -0.2599(3) 1.1338(3) 0.13540(10) 0.0888(7) Uani 1 1 d . . . C1 C 0.4036(7) 0.5752(7) -0.1039(3) 0.0596(18) Uani 1 1 d . . . H1A H 0.3027 0.5567 -0.0995 0.072 Uiso 1 1 calc R . . H1B H 0.4267 0.5552 -0.1344 0.072 Uiso 1 1 calc R . . C2 C 0.4865(8) 0.4844(9) -0.0754(3) 0.077(3) Uani 1 1 d . . . H2A H 0.4645 0.3855 -0.0820 0.092 Uiso 1 1 calc R . . H2B H 0.4594 0.5023 -0.0451 0.092 Uiso 1 1 calc R . . C3 C 0.7197(9) 0.4198(7) -0.1118(2) 0.0606(19) Uani 1 1 d . . . H3A H 0.8206 0.4430 -0.1108 0.073 Uiso 1 1 calc R . . H3B H 0.6854 0.4435 -0.1411 0.073 Uiso 1 1 calc R . . C4 C 0.7024(8) 0.2594(6) -0.10475(19) 0.0459(14) Uani 1 1 d . . . C5 C 0.7500(8) 0.1956(7) -0.0669(2) 0.0504(16) Uani 1 1 d . . . H5A H 0.7931 0.2494 -0.0449 0.061 Uiso 1 1 calc R . . C6 C 0.7329(7) 0.0492(6) -0.06202(19) 0.0453(14) Uani 1 1 d . . . H6A H 0.7688 0.0059 -0.0368 0.054 Uiso 1 1 calc R . . C7 C 0.6193(7) 0.0321(6) -0.12850(19) 0.0459(14) Uani 1 1 d . . . H7A H 0.5739 -0.0229 -0.1498 0.055 Uiso 1 1 calc R . . C8 C 0.6357(8) 0.1788(7) -0.13532(19) 0.0527(16) Uani 1 1 d . . . H8A H 0.6008 0.2208 -0.1609 0.063 Uiso 1 1 calc R . . C9 C 0.3511(6) 0.7939(8) -0.0593(2) 0.0510(16) Uani 1 1 d . . . H9A H 0.3722 0.8952 -0.0585 0.061 Uiso 1 1 calc R . . H9B H 0.3781 0.7534 -0.0312 0.061 Uiso 1 1 calc R . . C10 C 0.1907(6) 0.7735(7) -0.06611(18) 0.0411(13) Uani 1 1 d . . . C11 C 0.1104(6) 0.6779(8) -0.0409(2) 0.0497(14) Uani 1 1 d . . . H11A H 0.1544 0.6229 -0.0193 0.060 Uiso 1 1 calc R . . C12 C -0.0335(6) 0.6659(7) -0.04817(19) 0.0435(13) Uani 1 1 d . . . H12A H -0.0858 0.6033 -0.0307 0.052 Uiso 1 1 calc R . . C13 C -0.0262(7) 0.8305(7) -0.10380(19) 0.0480(14) Uani 1 1 d . . . H13A H -0.0730 0.8835 -0.1253 0.058 Uiso 1 1 calc R . . C14 C 0.1208(7) 0.8492(8) -0.0985(2) 0.0531(16) Uani 1 1 d . . . H14A H 0.1708 0.9118 -0.1165 0.064 Uiso 1 1 calc R . . C15 C 0.2651(8) 0.3632(7) 0.0394(2) 0.0516(15) Uani 1 1 d . . . C16 C 0.2920(11) 0.2391(8) 0.0096(2) 0.071(2) Uani 1 1 d . . . H16A H 0.2956 0.2720 -0.0210 0.085 Uiso 1 1 calc R . . C17 C 0.4324(11) 0.1595(10) 0.0211(5) 0.109(4) Uani 1 1 d . . . H17A H 0.4872 0.1404 -0.0054 0.131 Uiso 1 1 calc R . . H17B H 0.4902 0.2160 0.0410 0.131 Uiso 1 1 calc R . . C18 C 0.3873(9) 0.0224(9) 0.0426(3) 0.075(2) Uani 1 1 d . . . H18A H 0.4406 -0.0575 0.0306 0.090 Uiso 1 1 calc R . . H18B H 0.4030 0.0266 0.0741 0.090 Uiso 1 1 calc R . . C19 C 0.2359(8) 0.0077(7) 0.03280(18) 0.0487(15) Uani 1 1 d . . . N1 N 0.4356(5) 0.7278(5) -0.09366(16) 0.0392(10) Uani 1 1 d . . . H1C H 0.4147 0.7770 -0.1187 0.047 Uiso 1 1 calc R . . N2 N 0.6457(5) 0.5075(5) -0.08033(16) 0.0390(10) Uani 1 1 d . . . H2C H 0.6841 0.4853 -0.0537 0.047 Uiso 1 1 calc R . . N3 N 0.6683(5) -0.0313(5) -0.09145(16) 0.0376(10) Uani 1 1 d . . . N4 N -0.1022(5) 0.7402(5) -0.07940(15) 0.0370(10) Uani 1 1 d . . . N5 N 0.1899(7) 0.1260(6) 0.01353(19) 0.0615(16) Uani 1 1 d . . . H5B H 0.1039 0.1343 0.0040 0.074 Uiso 1 1 calc R . . O1 O 0.6545(4) 0.7537(4) -0.01373(14) 0.0401(10) Uani 1 1 d . . . O2 O 0.6884(4) 0.7187(4) -0.15819(15) 0.0407(10) Uani 1 1 d . . . O3 O 0.3546(6) 0.4627(5) 0.03811(15) 0.0599(13) Uani 1 1 d . . . O4 O 0.1558(6) 0.3654(6) 0.06258(19) 0.0745(15) Uani 1 1 d . . . O5 O 0.1618(6) -0.0992(5) 0.04034(16) 0.0615(13) Uani 1 1 d . . . O6 O -0.342(2) 1.0864(12) 0.1664(6) 0.303(12) Uani 1 1 d . . . O7 O -0.2024(15) 1.2618(10) 0.1444(4) 0.179(6) Uani 1 1 d . . . O8 O -0.1685(10) 1.0440(12) 0.1131(4) 0.150(4) Uani 1 1 d . . . O9 O -0.344(2) 1.179(4) 0.1038(8) 0.45(2) Uani 1 1 d . . . O10 O 0.8612(6) 0.9014(7) 0.03143(17) 0.0738(16) Uani 1 1 d . . . O11 O 0.6439(6) 0.4883(6) 0.02021(17) 0.0759(16) Uani 1 1 d . . . O12 O -0.1229(9) 0.3064(9) 0.0370(3) 0.112(2) 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 0.0252(3) 0.0260(3) 0.0432(3) -0.0003(2) -0.0009(2) 0.0006(2) Cl1 0.0613(13) 0.0907(18) 0.1144(17) -0.0401(14) 0.0078(12) 0.0144(11) C1 0.032(3) 0.043(4) 0.104(5) -0.018(3) -0.008(3) -0.003(3) C2 0.042(4) 0.067(5) 0.120(7) 0.020(5) -0.009(4) -0.025(4) C3 0.097(6) 0.025(3) 0.059(4) 0.005(3) 0.021(4) 0.005(3) C4 0.063(4) 0.026(3) 0.048(3) -0.001(2) 0.009(3) 0.009(3) C5 0.064(4) 0.034(3) 0.053(3) -0.005(2) -0.013(3) -0.003(3) C6 0.057(4) 0.031(3) 0.048(3) -0.001(2) -0.014(3) 0.000(3) C7 0.058(4) 0.025(3) 0.055(3) -0.002(2) -0.016(3) 0.003(2) C8 0.082(5) 0.036(3) 0.041(3) 0.001(2) -0.015(3) 0.006(3) C9 0.026(3) 0.071(5) 0.056(3) -0.017(3) -0.006(2) -0.003(3) C10 0.030(3) 0.050(4) 0.043(3) -0.012(2) -0.001(2) 0.002(3) C11 0.027(3) 0.066(4) 0.057(3) 0.003(3) -0.005(2) 0.003(3) C12 0.030(3) 0.048(4) 0.052(3) 0.011(2) 0.002(2) 0.006(2) C13 0.038(3) 0.056(4) 0.050(3) 0.012(3) -0.004(2) 0.000(3) C14 0.030(3) 0.066(4) 0.064(4) 0.002(3) 0.003(2) 0.003(3) C15 0.063(4) 0.048(4) 0.044(3) -0.001(3) 0.001(3) 0.006(3) C16 0.122(7) 0.048(4) 0.042(3) -0.003(3) 0.014(4) -0.027(4) C17 0.062(6) 0.061(6) 0.204(12) -0.012(7) 0.056(7) -0.002(5) C18 0.055(5) 0.056(5) 0.114(6) -0.011(4) 0.008(4) 0.003(4) C19 0.067(4) 0.037(3) 0.042(3) -0.004(2) -0.004(3) -0.003(3) N1 0.022(2) 0.040(3) 0.056(3) -0.002(2) 0.0029(19) -0.0004(18) N2 0.037(2) 0.026(2) 0.054(3) 0.0017(19) -0.002(2) 0.0003(18) N3 0.033(2) 0.028(2) 0.051(2) 0.002(2) -0.008(2) 0.0021(17) N4 0.027(2) 0.036(2) 0.048(3) 0.0014(19) -0.0024(18) 0.0034(18) N5 0.079(4) 0.041(3) 0.065(3) 0.004(2) -0.023(3) -0.006(3) O1 0.037(2) 0.042(2) 0.041(2) 0.0003(16) -0.0054(16) 0.0009(16) O2 0.038(2) 0.038(2) 0.046(2) -0.0023(17) -0.0014(17) -0.0044(17) O3 0.078(4) 0.042(3) 0.059(3) -0.013(2) 0.011(2) -0.007(2) O4 0.070(4) 0.072(4) 0.082(3) -0.024(3) 0.011(3) -0.010(3) O5 0.072(4) 0.046(3) 0.066(3) 0.002(2) -0.014(2) -0.001(2) O6 0.43(2) 0.101(8) 0.37(2) -0.036(11) 0.32(2) -0.077(12) O7 0.233(12) 0.085(6) 0.219(12) -0.034(7) 0.130(10) -0.021(7) O8 0.109(6) 0.145(8) 0.196(9) -0.081(7) 0.025(6) 0.031(6) O9 0.201(18) 0.87(6) 0.29(2) -0.25(3) -0.149(18) 0.24(3) O10 0.075(4) 0.090(4) 0.057(3) -0.008(3) -0.017(2) -0.014(3) O11 0.087(4) 0.061(3) 0.079(3) 0.023(3) -0.014(3) -0.021(3) O12 0.106(6) 0.114(6) 0.115(6) 0.003(5) -0.026(4) -0.006(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 N3 2.151(4) 1_565 ? Zn1 N4 2.163(5) 1_655 ? Zn1 O2 2.183(5) . ? Zn1 N2 2.193(5) . ? Zn1 N1 2.191(4) . ? Zn1 O1 2.231(5) . ? Cl1 O6 1.293(10) . ? Cl1 O9 1.31(2) . ? Cl1 O7 1.343(11) . ? Cl1 O8 1.378(8) . ? C1 C2 1.440(10) . ? C1 N1 1.494(8) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N2 1.514(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N2 1.440(8) . ? C3 C4 1.526(9) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C8 1.350(9) . ? C4 C5 1.371(9) . ? C5 C6 1.389(8) . ? C5 H5A 0.9300 . ? C6 N3 1.317(7) . ? C6 H6A 0.9300 . ? C7 N3 1.353(7) . ? C7 C8 1.398(8) . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? C9 N1 1.448(8) . ? C9 C10 1.529(8) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.399(9) . ? C10 C14 1.378(9) . ? C11 C12 1.371(8) . ? C11 H11A 0.9300 . ? C12 N4 1.342(7) . ? C12 H12A 0.9300 . ? C13 N4 1.331(8) . ? C13 C14 1.398(9) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 O3 1.254(9) . ? C15 O4 1.244(9) . ? C15 C16 1.494(9) . ? C16 N5 1.432(10) . ? C16 C17 1.552(14) . ? C16 H16A 0.9800 . ? C17 C18 1.501(13) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.455(11) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 O5 1.240(8) . ? C19 N5 1.325(8) . ? N1 H1C 0.9100 . ? N2 H2C 0.9100 . ? N3 Zn1 2.151(4) 1_545 ? N4 Zn1 2.163(5) 1_455 ? N5 H5B 0.8600 . ? 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 N3 Zn1 N4 90.20(18) 1_565 1_655 ? N3 Zn1 O2 91.46(17) 1_565 . ? N4 Zn1 O2 91.06(16) 1_655 . ? N3 Zn1 N2 174.28(18) 1_565 . ? N4 Zn1 N2 95.11(18) 1_655 . ? O2 Zn1 N2 90.57(17) . . ? N3 Zn1 N1 92.54(17) 1_565 . ? N4 Zn1 N1 177.21(19) 1_655 . ? O2 Zn1 N1 89.36(17) . . ? N2 Zn1 N1 82.13(18) . . ? N3 Zn1 O1 90.28(17) 1_565 . ? N4 Zn1 O1 87.25(16) 1_655 . ? O2 Zn1 O1 177.58(19) . . ? N2 Zn1 O1 87.85(17) . . ? N1 Zn1 O1 92.24(16) . . ? O6 Cl1 O9 106.9(18) . . ? O6 Cl1 O7 113.3(8) . . ? O9 Cl1 O7 95.7(19) . . ? O6 Cl1 O8 121.1(9) . . ? O9 Cl1 O8 102.2(11) . . ? O7 Cl1 O8 113.4(7) . . ? C2 C1 N1 109.4(6) . . ? C2 C1 H1A 109.8 . . ? N1 C1 H1A 109.8 . . ? C2 C1 H1B 109.8 . . ? N1 C1 H1B 109.8 . . ? H1A C1 H1B 108.2 . . ? C1 C2 N2 112.8(6) . . ? C1 C2 H2A 109.0 . . ? N2 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? N2 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? N2 C3 C4 114.6(5) . . ? N2 C3 H3A 108.6 . . ? C4 C3 H3A 108.6 . . ? N2 C3 H3B 108.6 . . ? C4 C3 H3B 108.6 . . ? H3A C3 H3B 107.6 . . ? C8 C4 C5 118.9(6) . . ? C8 C4 C3 120.2(6) . . ? C5 C4 C3 120.9(6) . . ? C4 C5 C6 118.9(6) . . ? C4 C5 H5A 120.6 . . ? C6 C5 H5A 120.6 . . ? N3 C6 C5 123.1(5) . . ? N3 C6 H6A 118.5 . . ? C5 C6 H6A 118.5 . . ? N3 C7 C8 121.2(5) . . ? N3 C7 H7A 119.4 . . ? C8 C7 H7A 119.4 . . ? C4 C8 C7 119.9(5) . . ? C4 C8 H8A 120.0 . . ? C7 C8 H8A 120.0 . . ? N1 C9 C10 112.8(5) . . ? N1 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? N1 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C14 117.7(6) . . ? C11 C10 C9 122.3(5) . . ? C14 C10 C9 119.9(6) . . ? C10 C11 C12 119.5(6) . . ? C10 C11 H11A 120.2 . . ? C12 C11 H11A 120.2 . . ? N4 C12 C11 122.9(6) . . ? N4 C12 H12A 118.5 . . ? C11 C12 H12A 118.5 . . ? N4 C13 C14 122.8(6) . . ? N4 C13 H13A 118.6 . . ? C14 C13 H13A 118.6 . . ? C10 C14 C13 119.1(6) . . ? C10 C14 H14A 120.4 . . ? C13 C14 H14A 120.4 . . ? O3 C15 O4 123.7(6) . . ? O3 C15 C16 116.6(6) . . ? O4 C15 C16 119.7(7) . . ? N5 C16 C15 114.4(7) . . ? N5 C16 C17 101.0(6) . . ? C15 C16 C17 112.4(8) . . ? N5 C16 H16A 109.6 . . ? C15 C16 H16A 109.6 . . ? C17 C16 H16A 109.6 . . ? C18 C17 C16 105.7(7) . . ? C18 C17 H17A 110.6 . . ? C16 C17 H17A 110.6 . . ? C18 C17 H17B 110.6 . . ? C16 C17 H17B 110.6 . . ? H17A C17 H17B 108.7 . . ? C19 C18 C17 105.5(8) . . ? C19 C18 H18A 110.6 . . ? C17 C18 H18A 110.7 . . ? C19 C18 H18B 110.7 . . ? C17 C18 H18B 110.6 . . ? H18A C18 H18B 108.8 . . ? O5 C19 N5 125.1(7) . . ? O5 C19 C18 125.8(7) . . ? N5 C19 C18 109.1(6) . . ? C9 N1 C1 116.7(5) . . ? C9 N1 Zn1 117.0(4) . . ? C1 N1 Zn1 105.5(3) . . ? C9 N1 H1C 105.5 . . ? C1 N1 H1C 105.5 . . ? Zn1 N1 H1C 105.5 . . ? C3 N2 C2 117.2(6) . . ? C3 N2 Zn1 117.3(4) . . ? C2 N2 Zn1 104.2(4) . . ? C3 N2 H2C 105.7 . . ? C2 N2 H2C 105.7 . . ? Zn1 N2 H2C 105.7 . . ? C6 N3 C7 118.0(5) . . ? C6 N3 Zn1 121.9(4) . 1_545 ? C7 N3 Zn1 119.4(4) . 1_545 ? C13 N4 C12 117.8(5) . . ? C13 N4 Zn1 118.4(4) . 1_455 ? C12 N4 Zn1 123.4(4) . 1_455 ? C19 N5 C16 116.0(7) . . ? C19 N5 H5B 122.0 . . ? C16 N5 H5B 122.0 . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.586 _refine_diff_density_min -0.490 _refine_diff_density_rms 0.078 _database_code_depnum_ccdc_archive 'CCDC 953112'