# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email zdenek.travnicek@upol.cz _publ_contact_author_name 'Zdenek Travnicek' loop_ _publ_author_name Z.Travnicek R.Novotna J.Marek I.PopaM.Sipl data_Travnicek1 _database_code_depnum_ccdc_archive 'CCDC 809163' #TrackingRef 'deposit-compound1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H14 Cl3 N5 Zn, H2 O ' _chemical_formula_sum 'C10 H16 Cl3 N5 O Zn' _chemical_formula_weight 394.00 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.4767(3) _cell_length_b 9.9382(3) _cell_length_c 14.0372(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.646(3) _cell_angle_gamma 90.00 _cell_volume 1599.34(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 12065 _cell_measurement_theta_min 2.7097 _cell_measurement_theta_max 31.9757 _exptl_crystal_description prism _exptl_crystal_colour white _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 2.038 _exptl_absorpt_correction_T_min 0.85524 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 8.3611 _diffrn_measurement_device_type 'Xcalibur2 + CCD' _diffrn_measurement_method 'rotation method, \w--scan' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9458 _diffrn_reflns_av_R_equivalents 0.0144 _diffrn_reflns_av_sigmaI/netI 0.0103 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2811 _reflns_number_gt 2778 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2006)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2006)' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2006)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0050P)^2^+5.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2811 _refine_ls_number_parameters 191 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.0905 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 1.591 _refine_ls_restrained_S_all 1.591 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn Zn 0.26230(4) 0.62144(5) 0.10869(3) 0.01536(13) Uani 1 1 d . . . Cl1 Cl 0.43456(8) 0.72748(10) 0.09537(7) 0.0188(2) Uani 1 1 d . . . Cl2 Cl 0.24214(9) 0.59279(11) 0.26808(7) 0.0242(2) Uani 1 1 d . . . Cl3 Cl 0.10766(9) 0.69945(11) 0.02500(9) 0.0276(3) Uani 1 1 d . . . N1 N 0.5251(3) 0.2044(3) 0.1379(2) 0.0177(7) Uani 1 1 d . . . H1 H 0.5919 0.1981 0.1680 0.021 Uiso 1 1 calc R . . C2 C 0.4738(4) 0.0884(4) 0.1042(3) 0.0198(9) Uani 1 1 d . . . H2 H 0.5152 0.0086 0.1133 0.024 Uiso 1 1 calc R . . N3 N 0.3719(3) 0.0813(4) 0.0605(3) 0.0221(8) Uani 1 1 d . . . C4 C 0.3192(4) 0.2026(4) 0.0540(3) 0.0178(9) Uani 1 1 d . . . C5 C 0.3622(3) 0.3260(4) 0.0848(3) 0.0155(8) Uani 1 1 d . . . C6 C 0.4770(3) 0.3293(4) 0.1268(3) 0.0155(8) Uani 1 1 d . . . N6 N 0.5368(3) 0.4370(3) 0.1529(2) 0.0165(7) Uani 1 1 d . . . H6 H 0.5029 0.5141 0.1490 0.020 Uiso 1 1 calc R . . N7 N 0.2806(3) 0.4255(3) 0.0633(2) 0.0182(7) Uani 1 1 d . . . C8 C 0.1915(4) 0.3608(4) 0.0206(3) 0.0223(9) Uani 1 1 d . . . H8 H 0.1231 0.4027 -0.0016 0.027 Uiso 1 1 calc R . . N9 N 0.2112(3) 0.2279(4) 0.0129(3) 0.0208(8) Uani 1 1 d . . . H9 H 0.1644 0.1696 -0.0130 0.025 Uiso 1 1 calc R . . C9 C 0.6594(3) 0.4309(4) 0.1885(3) 0.0186(9) Uani 1 1 d . . . H9A H 0.7044 0.3804 0.1438 0.022 Uiso 1 1 calc R . . H9B H 0.6640 0.3837 0.2490 0.022 Uiso 1 1 calc R . . C10 C 0.7113(4) 0.5686(4) 0.2014(3) 0.0178(9) Uani 1 1 d . A . H10 H 0.6634 0.6436 0.1927 0.021 Uiso 1 1 calc R . . C11 C 0.8250(4) 0.5867(5) 0.2252(3) 0.0282(11) Uani 1 1 d . . . C12 C 0.8752(4) 0.7252(5) 0.2393(4) 0.0300(11) Uani 1 1 d . A . H12A H 0.8130 0.7897 0.2406 0.045 Uiso 1 1 calc R . . H12B H 0.9243 0.7460 0.1877 0.045 Uiso 1 1 calc R . . H12C H 0.9204 0.7285 0.2985 0.045 Uiso 1 1 calc R . . C13A C 0.9098(4) 0.4770(5) 0.2300(5) 0.0297(15) Uani 0.819(8) 1 d P A 1 H13A H 0.9369 0.4636 0.2950 0.045 Uiso 0.819(8) 1 calc PR A 1 H13B H 0.9746 0.4994 0.1921 0.045 Uiso 0.819(8) 1 calc PR A 1 H13C H 0.8735 0.3960 0.2060 0.045 Uiso 0.819(8) 1 calc PR A 1 C13B C 0.840(2) 0.514(2) 0.340(2) 0.0297(15) Uani 0.181(8) 1 d P A 2 H13D H 0.8036 0.5711 0.3849 0.045 Uiso 0.181(8) 1 calc PR A 2 H13E H 0.9218 0.5055 0.3579 0.045 Uiso 0.181(8) 1 calc PR A 2 H13F H 0.8044 0.4272 0.3392 0.045 Uiso 0.181(8) 1 calc PR A 2 O1 O 0.0944(3) 0.0096(3) -0.0602(2) 0.0232(7) Uiso 1 1 d D . . H1V H 0.133(5) -0.016(7) -0.110(3) 0.07(2) Uiso 1 1 d D . . H1W H 0.111(6) -0.061(5) -0.024(4) 0.08(2) Uiso 1 1 d 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 Zn 0.0144(2) 0.0132(2) 0.0183(2) -0.00090(19) 0.00002(18) 0.00100(18) Cl1 0.0181(5) 0.0133(5) 0.0253(5) 0.0033(4) 0.0056(4) -0.0002(4) Cl2 0.0267(5) 0.0272(6) 0.0189(5) -0.0018(4) 0.0044(4) -0.0129(4) Cl3 0.0216(5) 0.0184(5) 0.0416(7) 0.0018(5) -0.0105(5) 0.0033(4) N1 0.0203(18) 0.0166(18) 0.0161(17) 0.0004(14) -0.0009(14) 0.0021(14) C2 0.028(2) 0.0092(19) 0.022(2) 0.0004(17) 0.0013(18) 0.0015(17) N3 0.029(2) 0.0147(18) 0.0227(19) -0.0017(15) 0.0012(16) -0.0005(15) C4 0.020(2) 0.017(2) 0.017(2) -0.0012(17) 0.0011(16) -0.0003(17) C5 0.018(2) 0.014(2) 0.0150(19) 0.0002(16) 0.0033(16) 0.0020(16) C6 0.019(2) 0.013(2) 0.0148(19) 0.0000(16) 0.0029(16) 0.0015(16) N6 0.0156(17) 0.0114(17) 0.0226(18) 0.0004(14) 0.0009(14) 0.0025(14) N7 0.0205(18) 0.0133(17) 0.0207(18) -0.0014(14) 0.0001(14) 0.0013(14) C8 0.018(2) 0.021(2) 0.027(2) -0.0018(19) -0.0017(17) 0.0009(18) N9 0.0203(18) 0.0163(18) 0.0254(19) -0.0049(15) -0.0043(15) -0.0037(15) C9 0.017(2) 0.015(2) 0.024(2) 0.0007(17) 0.0014(17) 0.0021(17) C10 0.019(2) 0.014(2) 0.021(2) 0.0011(16) 0.0023(16) 0.0023(17) C11 0.032(3) 0.027(3) 0.027(2) -0.010(2) 0.013(2) -0.008(2) C12 0.028(2) 0.026(3) 0.037(3) -0.007(2) 0.005(2) -0.012(2) C13A 0.012(2) 0.012(3) 0.063(4) 0.000(3) -0.019(2) -0.003(2) C13B 0.012(2) 0.012(3) 0.063(4) 0.000(3) -0.019(2) -0.003(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 Zn N7 2.062(3) . ? Zn Cl3 2.2223(11) . ? Zn Cl1 2.2557(11) . ? Zn Cl2 2.2778(11) . ? N1 C6 1.365(5) . ? N1 C2 1.368(5) . ? N1 H1 0.8600 . ? C2 N3 1.298(6) . ? C2 H2 0.9300 . ? N3 C4 1.350(6) . ? C4 N9 1.365(5) . ? C4 C5 1.384(6) . ? C5 N7 1.386(5) . ? C5 C6 1.418(6) . ? C6 N6 1.314(5) . ? N6 C9 1.473(5) . ? N6 H6 0.8600 . ? N7 C8 1.327(5) . ? C8 N9 1.345(6) . ? C8 H8 0.9300 . ? N9 H9 0.8600 . ? C9 C10 1.500(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.345(6) . ? C10 H10 0.9300 . ? C11 C13A 1.460(7) . ? C11 C12 1.501(6) . ? C11 C13B 1.76(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13A H13A 0.9600 . ? C13A H13B 0.9600 . ? C13A H13C 0.9600 . ? C13B H13D 0.9600 . ? C13B H13E 0.9600 . ? C13B H13F 0.9600 . ? O1 H1V 0.88(5) . ? O1 H1W 0.88(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N7 Zn Cl3 104.85(10) . . ? N7 Zn Cl1 108.28(10) . . ? Cl3 Zn Cl1 118.35(4) . . ? N7 Zn Cl2 101.63(10) . . ? Cl3 Zn Cl2 116.62(5) . . ? Cl1 Zn Cl2 105.60(4) . . ? C6 N1 C2 124.1(4) . . ? C6 N1 H1 117.9 . . ? C2 N1 H1 117.9 . . ? N3 C2 N1 125.0(4) . . ? N3 C2 H2 117.5 . . ? N1 C2 H2 117.5 . . ? C2 N3 C4 112.0(4) . . ? N3 C4 N9 126.0(4) . . ? N3 C4 C5 128.2(4) . . ? N9 C4 C5 105.8(4) . . ? C4 C5 N7 109.7(3) . . ? C4 C5 C6 117.5(4) . . ? N7 C5 C6 132.8(4) . . ? N6 C6 N1 120.4(4) . . ? N6 C6 C5 126.7(4) . . ? N1 C6 C5 112.9(4) . . ? C6 N6 C9 122.6(3) . . ? C6 N6 H6 118.7 . . ? C9 N6 H6 118.7 . . ? C8 N7 C5 104.5(3) . . ? C8 N7 Zn 120.7(3) . . ? C5 N7 Zn 133.2(3) . . ? N7 C8 N9 112.5(4) . . ? N7 C8 H8 123.7 . . ? N9 C8 H8 123.7 . . ? C8 N9 C4 107.4(4) . . ? C8 N9 H9 126.3 . . ? C4 N9 H9 126.3 . . ? N6 C9 C10 111.8(3) . . ? N6 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? N6 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C9 121.8(4) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C10 C11 C13A 123.2(4) . . ? C10 C11 C12 121.2(4) . . ? C13A C11 C12 115.3(4) . . ? C10 C11 C13B 103.2(8) . . ? C13A C11 C13B 67.4(9) . . ? C12 C11 C13B 103.4(8) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13A H13A 109.5 . . ? C11 C13A H13B 109.5 . . ? C11 C13A H13C 109.5 . . ? C11 C13B H13D 109.5 . . ? C11 C13B H13E 109.5 . . ? H13D C13B H13E 109.5 . . ? C11 C13B H13F 109.5 . . ? H13D C13B H13F 109.5 . . ? H13E C13B H13F 109.5 . . ? H1V O1 H1W 97(6) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.732 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.089 # Attachment 'deposit-compound2.cif' data_Travnicek2 _database_code_depnum_ccdc_archive 'CCDC 809164' #TrackingRef 'deposit-compound2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H28 Cl8 N10 Zn3' _chemical_formula_sum 'C20 H28 Cl8 N10 Zn3' _chemical_formula_weight 888.23 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' 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 triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3518(3) _cell_length_b 10.0642(5) _cell_length_c 21.5006(10) _cell_angle_alpha 96.082(4) _cell_angle_beta 94.259(4) _cell_angle_gamma 112.541(4) _cell_volume 1646.72(13) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 15153 _cell_measurement_theta_min 2.6550 _cell_measurement_theta_max 31.7910 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.791 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 2.848 _exptl_absorpt_correction_T_min 0.63460 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 8.3611 _diffrn_measurement_device_type 'Xcalibur2 + CCD' _diffrn_measurement_method 'rotation method, \w--scan' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11581 _diffrn_reflns_av_R_equivalents 0.0082 _diffrn_reflns_av_sigmaI/netI 0.0079 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5752 _reflns_number_gt 5592 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2006)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2006)' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2006)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+2.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5752 _refine_ls_number_parameters 395 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0223 _refine_ls_R_factor_gt 0.0214 _refine_ls_wR_factor_ref 0.0702 _refine_ls_wR_factor_gt 0.0695 _refine_ls_goodness_of_fit_ref 1.169 _refine_ls_restrained_S_all 1.169 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.69990(3) 0.33123(3) 0.082146(12) 0.01150(8) Uani 1 1 d . . . Zn2 Zn 0.60769(4) 0.33127(3) 0.251629(13) 0.01605(8) Uani 1 1 d . . . Zn3 Zn 0.69511(4) 0.57733(3) 0.412818(13) 0.01595(8) Uani 1 1 d . . . Cl1 Cl 0.73094(8) 0.54841(6) 0.06154(3) 0.01897(13) Uani 1 1 d . . . Cl2 Cl 0.80973(7) 0.19414(6) 0.02298(3) 0.01456(12) Uani 1 1 d . . . Cl3 Cl 0.81141(8) 0.32389(7) 0.18251(3) 0.01801(13) Uani 1 1 d . . . Cl4 Cl 0.40783(9) 0.40239(7) 0.21230(3) 0.02290(14) Uani 1 1 d . . . Cl5 Cl 0.49631(9) 0.11413(7) 0.28347(3) 0.02229(14) Uani 1 1 d . . . Cl6 Cl 0.81477(8) 0.51533(7) 0.32583(3) 0.02293(14) Uani 1 1 d . . . Cl7 Cl 0.50130(9) 0.66811(7) 0.38573(3) 0.02399(14) Uani 1 1 d . . . Cl8 Cl 0.92220(8) 0.71035(7) 0.48512(3) 0.02119(14) Uani 1 1 d . . . N1 N 0.2694(3) -0.1427(2) 0.13962(9) 0.0123(4) Uani 1 1 d . . . C2 C 0.1032(3) -0.1467(3) 0.13849(11) 0.0155(5) Uani 1 1 d . . . H2 H 0.0213 -0.2257 0.1530 0.019 Uiso 1 1 calc R . . N3 N 0.0481(3) -0.0518(2) 0.11925(10) 0.0171(4) Uani 1 1 d . . . C4 C 0.1775(3) 0.0605(3) 0.10013(11) 0.0138(5) Uani 1 1 d . . . C5 C 0.3487(3) 0.0785(2) 0.09956(11) 0.0118(5) Uani 1 1 d . . . C6 C 0.3977(3) -0.0342(2) 0.11598(11) 0.0121(5) Uani 1 1 d . . . N6 N 0.5498(3) -0.0393(2) 0.10760(10) 0.0146(4) Uani 1 1 d . . . H6 H 0.6250 0.0311 0.0925 0.017 Uiso 1 1 calc R . . N7 N 0.4396(2) 0.2046(2) 0.07522(9) 0.0123(4) Uani 1 1 d . . . C8 C 0.3216(3) 0.2588(3) 0.06174(11) 0.0148(5) Uani 1 1 d . . . H8 H 0.3461 0.3449 0.0449 0.018 Uiso 1 1 calc R . . N9 N 0.1627(3) 0.1754(2) 0.07516(10) 0.0155(4) Uani 1 1 d . . . H9 H 0.0690 0.1912 0.0692 0.019 Uiso 1 1 calc R . . C9 C 0.5973(3) -0.1588(3) 0.12278(13) 0.0205(5) Uani 1 1 d D . . H9A H 0.7225 -0.1235 0.1346 0.025 Uiso 1 1 calc R . . H9B H 0.5646 -0.2336 0.0864 0.025 Uiso 1 1 calc R . . C10 C 0.5016(3) -0.2203(3) 0.17697(12) 0.0185(5) Uani 1 1 d D . . H10A H 0.5440 -0.1470 0.2141 0.022 Uiso 1 1 calc R . . H10B H 0.5277 -0.3027 0.1863 0.022 Uiso 1 1 calc R . . C11 C 0.3033(3) -0.2693(2) 0.16293(11) 0.0141(5) Uani 1 1 d D . . C12 C 0.2248(3) -0.3008(3) 0.22434(12) 0.0206(5) Uani 1 1 d . . . H12A H 0.2644 -0.3672 0.2429 0.031 Uiso 1 1 calc R . . H12B H 0.0997 -0.3433 0.2157 0.031 Uiso 1 1 calc R . . H12C H 0.2611 -0.2118 0.2530 0.031 Uiso 1 1 calc R . . C13 C 0.2218(3) -0.4007(3) 0.11121(12) 0.0181(5) Uani 1 1 d . . . H13A H 0.2806 -0.3803 0.0745 0.027 Uiso 1 1 calc R . . H13B H 0.1003 -0.4207 0.1008 0.027 Uiso 1 1 calc R . . H13C H 0.2334 -0.4838 0.1259 0.027 Uiso 1 1 calc R . . N1A N 0.1524(3) 0.0933(2) 0.37840(10) 0.0166(4) Uani 1 1 d . . . C2A C 0.1796(3) -0.0101(3) 0.40868(12) 0.0191(5) Uani 1 1 d . A . H2A H 0.0895 -0.1020 0.4024 0.023 Uiso 1 1 calc R . . N3A N 0.3194(3) 0.0069(2) 0.44557(10) 0.0177(4) Uani 1 1 d . . . C4A C 0.4436(3) 0.1438(3) 0.45189(11) 0.0138(5) Uani 1 1 d . A . C5A C 0.4299(3) 0.2584(3) 0.42601(11) 0.0138(5) Uani 1 1 d . . . C6A C 0.2743(3) 0.2347(3) 0.38693(11) 0.0145(5) Uani 1 1 d . A . N6A N 0.2450(3) 0.3356(3) 0.36080(10) 0.0196(5) Uani 1 1 d . . . H6A H 0.316(4) 0.413(4) 0.3656(15) 0.023 Uiso 1 1 d . . . N7A N 0.5840(3) 0.3800(2) 0.44302(9) 0.0154(4) Uani 1 1 d . A . C8A C 0.6861(3) 0.3358(3) 0.47818(12) 0.0176(5) Uani 1 1 d . . . H8A H 0.7991 0.3956 0.4964 0.021 Uiso 1 1 calc R A . N9A N 0.6073(3) 0.1945(2) 0.48447(10) 0.0157(4) Uani 1 1 d . A . H9A1 H 0.6515 0.1454 0.5051 0.019 Uiso 1 1 calc R . . C9A C 0.0834(10) 0.3081(6) 0.3212(4) 0.0232(10) Uani 0.823(5) 1 d PD A 1 H9A2 H 0.1061 0.3743 0.2902 0.028 Uiso 0.823(5) 1 calc PR A 1 H9A3 H 0.0000 0.3243 0.3469 0.028 Uiso 0.823(5) 1 calc PR A 1 C10A C 0.0082(4) 0.1519(3) 0.28808(15) 0.0229(7) Uani 0.823(5) 1 d PD A 1 H10C H -0.1025 0.1321 0.2634 0.027 Uiso 0.823(5) 1 calc PR A 1 H10D H 0.0874 0.1388 0.2595 0.027 Uiso 0.823(5) 1 calc PR A 1 C11A C -0.0196(10) 0.0439(5) 0.3362(3) 0.0165(9) Uani 0.823(5) 1 d PD A 1 C12A C -0.1615(4) 0.0370(5) 0.37602(16) 0.0261(8) Uani 0.823(5) 1 d P A 1 H12D H -0.1351 0.1316 0.3989 0.039 Uiso 0.823(5) 1 calc PR A 1 H12E H -0.1695 -0.0306 0.4052 0.039 Uiso 0.823(5) 1 calc PR A 1 H12F H -0.2708 0.0054 0.3495 0.039 Uiso 0.823(5) 1 calc PR A 1 C13A C -0.0612(5) -0.1061(4) 0.29664(17) 0.0280(8) Uani 0.823(5) 1 d P A 1 H13D H -0.1016 -0.1810 0.3228 0.042 Uiso 0.823(5) 1 calc PR A 1 H13E H 0.0425 -0.1068 0.2804 0.042 Uiso 0.823(5) 1 calc PR A 1 H13F H -0.1502 -0.1234 0.2623 0.042 Uiso 0.823(5) 1 calc PR A 1 C9B C 0.097(5) 0.334(4) 0.315(2) 0.0232(10) Uani 0.177 1 d PD A 2 H9B1 H 0.1100 0.3070 0.2712 0.028 Uiso 0.177(5) 1 calc PR A 2 H9B2 H 0.0829 0.4256 0.3194 0.028 Uiso 0.177(5) 1 calc PR A 2 C10B C -0.047(2) 0.2143(16) 0.3394(7) 0.0229(7) Uani 0.177 1 d PD A 2 H10E H -0.0484 0.2423 0.3839 0.027 Uiso 0.177(5) 1 calc PR A 2 H10F H -0.1594 0.1986 0.3170 0.027 Uiso 0.177(5) 1 calc PR A 2 C11B C -0.014(6) 0.074(3) 0.3297(19) 0.0165(9) Uani 0.177 1 d PD A 2 C12B C 0.009(2) 0.0186(19) 0.2728(7) 0.0261(8) Uani 0.177 1 d P A 2 H12G H 0.0349 -0.0655 0.2767 0.039 Uiso 0.177(5) 1 calc PR A 2 H12H H 0.1046 0.0906 0.2572 0.039 Uiso 0.177(5) 1 calc PR A 2 H12I H -0.0954 -0.0084 0.2440 0.039 Uiso 0.177(5) 1 calc PR A 2 C13B C -0.169(2) -0.043(2) 0.3635(8) 0.0280(8) Uani 0.177 1 d P A 2 H13G H -0.2813 -0.0494 0.3458 0.042 Uiso 0.177(5) 1 calc PR A 2 H13H H -0.1521 -0.0105 0.4080 0.042 Uiso 0.177(5) 1 calc PR A 2 H13I H -0.1642 -0.1372 0.3562 0.042 Uiso 0.177(5) 1 calc PR A 2 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 0.01102(14) 0.01054(14) 0.01323(14) 0.00256(10) 0.00078(10) 0.00447(11) Zn2 0.02151(16) 0.01597(15) 0.01360(15) 0.00287(11) 0.00186(11) 0.01044(12) Zn3 0.01928(15) 0.01248(15) 0.01487(15) 0.00211(11) 0.00133(11) 0.00506(12) Cl1 0.0202(3) 0.0119(3) 0.0248(3) 0.0060(2) -0.0001(2) 0.0060(2) Cl2 0.0138(3) 0.0187(3) 0.0134(3) 0.0011(2) 0.0011(2) 0.0091(2) Cl3 0.0188(3) 0.0256(3) 0.0122(3) 0.0024(2) 0.0001(2) 0.0119(2) Cl4 0.0295(3) 0.0252(3) 0.0214(3) 0.0051(2) 0.0008(2) 0.0189(3) Cl5 0.0307(3) 0.0179(3) 0.0230(3) 0.0067(2) 0.0074(3) 0.0131(3) Cl6 0.0240(3) 0.0239(3) 0.0180(3) -0.0030(2) 0.0034(2) 0.0077(3) Cl7 0.0306(3) 0.0178(3) 0.0273(3) 0.0039(2) 0.0011(3) 0.0139(3) Cl8 0.0213(3) 0.0195(3) 0.0166(3) 0.0003(2) 0.0001(2) 0.0023(2) N1 0.0118(10) 0.0109(9) 0.0143(10) 0.0024(8) 0.0006(8) 0.0045(8) C2 0.0114(11) 0.0139(12) 0.0197(12) 0.0009(9) 0.0026(9) 0.0036(9) N3 0.0106(10) 0.0149(10) 0.0254(11) 0.0022(8) 0.0021(8) 0.0048(8) C4 0.0139(11) 0.0115(11) 0.0158(11) -0.0007(9) 0.0005(9) 0.0056(9) C5 0.0109(11) 0.0117(11) 0.0123(11) -0.0002(9) -0.0001(8) 0.0046(9) C6 0.0114(11) 0.0098(11) 0.0130(11) -0.0005(9) -0.0010(9) 0.0028(9) N6 0.0105(10) 0.0108(10) 0.0243(11) 0.0057(8) 0.0044(8) 0.0051(8) N7 0.0123(10) 0.0111(9) 0.0139(10) 0.0023(7) 0.0005(7) 0.0051(8) C8 0.0162(12) 0.0134(11) 0.0162(12) 0.0023(9) 0.0004(9) 0.0075(10) N9 0.0112(10) 0.0142(10) 0.0239(11) 0.0031(8) -0.0002(8) 0.0084(8) C9 0.0145(12) 0.0164(13) 0.0357(15) 0.0103(11) 0.0059(11) 0.0094(10) C10 0.0150(12) 0.0158(12) 0.0263(13) 0.0072(10) -0.0005(10) 0.0074(10) C11 0.0154(12) 0.0100(11) 0.0178(12) 0.0046(9) 0.0013(9) 0.0055(9) C12 0.0231(13) 0.0203(13) 0.0204(13) 0.0077(10) 0.0056(10) 0.0089(11) C13 0.0202(13) 0.0136(12) 0.0221(13) 0.0029(10) 0.0001(10) 0.0089(10) N1A 0.0127(10) 0.0207(11) 0.0157(10) 0.0067(8) -0.0001(8) 0.0053(9) C2A 0.0157(12) 0.0180(12) 0.0208(13) 0.0070(10) -0.0009(10) 0.0030(10) N3A 0.0143(10) 0.0169(11) 0.0209(11) 0.0063(8) -0.0006(8) 0.0049(9) C4A 0.0128(11) 0.0181(12) 0.0117(11) 0.0035(9) 0.0009(9) 0.0072(10) C5A 0.0133(11) 0.0159(12) 0.0136(11) 0.0031(9) 0.0036(9) 0.0069(9) C6A 0.0146(12) 0.0190(12) 0.0123(11) 0.0037(9) 0.0040(9) 0.0084(10) N6A 0.0195(11) 0.0185(11) 0.0216(11) 0.0047(9) -0.0029(9) 0.0090(9) N7A 0.0152(10) 0.0151(10) 0.0157(10) 0.0040(8) 0.0005(8) 0.0054(8) C8A 0.0157(12) 0.0164(12) 0.0178(12) 0.0028(10) -0.0009(9) 0.0035(10) N9A 0.0129(10) 0.0163(10) 0.0187(10) 0.0050(8) -0.0014(8) 0.0065(8) C9A 0.0215(19) 0.023(3) 0.029(3) 0.0142(19) -0.0019(14) 0.0109(19) C10A 0.0214(16) 0.0241(17) 0.0230(16) 0.0085(13) -0.0035(12) 0.0087(13) C11A 0.0131(14) 0.019(3) 0.016(2) 0.0114(18) -0.0037(13) 0.004(2) C12A 0.0162(16) 0.037(2) 0.0230(17) 0.0040(15) -0.0008(12) 0.0094(15) C13A 0.0324(19) 0.0242(18) 0.0262(18) -0.0030(14) -0.0085(14) 0.0135(15) C9B 0.0215(19) 0.023(3) 0.029(3) 0.0142(19) -0.0019(14) 0.0109(19) C10B 0.0214(16) 0.0241(17) 0.0230(16) 0.0085(13) -0.0035(12) 0.0087(13) C11B 0.0131(14) 0.019(3) 0.016(2) 0.0114(18) -0.0037(13) 0.004(2) C12B 0.0162(16) 0.037(2) 0.0230(17) 0.0040(15) -0.0008(12) 0.0094(15) C13B 0.0324(19) 0.0242(18) 0.0262(18) -0.0030(14) -0.0085(14) 0.0135(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 N7 2.040(2) . ? Zn1 Cl1 2.1975(6) . ? Zn1 Cl2 2.2660(6) . ? Zn1 Cl3 2.3059(6) . ? Zn2 Cl4 2.2018(7) . ? Zn2 Cl5 2.2278(7) . ? Zn2 Cl6 2.3399(7) . ? Zn2 Cl3 2.3576(6) . ? Zn3 N7A 2.044(2) . ? Zn3 Cl7 2.2137(7) . ? Zn3 Cl8 2.2316(7) . ? Zn3 Cl6 2.3227(7) . ? N1 C2 1.371(3) . ? N1 C6 1.379(3) . ? N1 C11 1.532(3) . ? C2 N3 1.299(3) . ? C2 H2 0.9300 . ? N3 C4 1.357(3) . ? C4 N9 1.368(3) . ? C4 C5 1.372(3) . ? C5 N7 1.386(3) . ? C5 C6 1.414(3) . ? C6 N6 1.316(3) . ? N6 C9 1.463(3) . ? N6 H6 0.8600 . ? N7 C8 1.325(3) . ? C8 N9 1.343(3) . ? C8 H8 0.9300 . ? N9 H9 0.8600 . ? C9 C10 1.514(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.531(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.527(3) . ? C11 C13 1.528(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? N1A C2A 1.364(3) . ? N1A C6A 1.379(3) . ? N1A C11A 1.516(8) . ? N1A C11B 1.61(4) . ? C2A N3A 1.304(3) . ? C2A H2A 0.9300 . ? N3A C4A 1.355(3) . ? C4A N9A 1.367(3) . ? C4A C5A 1.372(3) . ? C5A N7A 1.384(3) . ? C5A C6A 1.417(3) . ? C6A N6A 1.303(3) . ? N6A C9A 1.455(9) . ? N6A C9B 1.52(5) . ? N6A H6A 0.77(3) . ? N7A C8A 1.327(3) . ? C8A N9A 1.345(3) . ? C8A H8A 0.9300 . ? N9A H9A1 0.8600 . ? C9A C10A 1.520(7) . ? C9A H9A2 0.9700 . ? C9A H9A3 0.9700 . ? C10A C11A 1.545(4) . ? C10A H10C 0.9700 . ? C10A H10D 0.9700 . ? C11A C13A 1.551(7) . ? C11A C12A 1.497(7) . ? C12A H12D 0.9600 . ? C12A H12E 0.9600 . ? C12A H12F 0.9600 . ? C13A H13D 0.9600 . ? C13A H13E 0.9600 . ? C13A H13F 0.9600 . ? C9B C10B 1.519(10) . ? C9B H9B1 0.9700 . ? C9B H9B2 0.9700 . ? C10B C11B 1.538(9) . ? C10B H10E 0.9700 . ? C10B H10F 0.9700 . ? C11B C13B 1.65(4) . ? C11B C12B 1.35(4) . ? C12B H12G 0.9600 . ? C12B H12H 0.9600 . ? C12B H12I 0.9600 . ? C13B H13G 0.9600 . ? C13B H13H 0.9600 . ? C13B H13I 0.9600 . ? 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 N7 Zn1 Cl1 108.60(6) . . ? N7 Zn1 Cl2 104.23(6) . . ? Cl1 Zn1 Cl2 120.95(2) . . ? N7 Zn1 Cl3 104.90(6) . . ? Cl1 Zn1 Cl3 115.27(3) . . ? Cl2 Zn1 Cl3 101.30(2) . . ? Cl4 Zn2 Cl5 113.49(3) . . ? Cl4 Zn2 Cl6 111.02(3) . . ? Cl5 Zn2 Cl6 114.94(3) . . ? Cl4 Zn2 Cl3 114.13(2) . . ? Cl5 Zn2 Cl3 107.35(2) . . ? Cl6 Zn2 Cl3 94.48(2) . . ? N7A Zn3 Cl7 112.70(6) . . ? N7A Zn3 Cl8 105.75(6) . . ? Cl7 Zn3 Cl8 118.86(3) . . ? N7A Zn3 Cl6 100.82(6) . . ? Cl7 Zn3 Cl6 111.38(3) . . ? Cl8 Zn3 Cl6 105.56(3) . . ? Zn1 Cl3 Zn2 108.30(2) . . ? Zn3 Cl6 Zn2 112.88(3) . . ? C2 N1 C6 120.9(2) . . ? C2 N1 C11 117.72(19) . . ? C6 N1 C11 121.19(19) . . ? N3 C2 N1 126.9(2) . . ? N3 C2 H2 116.6 . . ? N1 C2 H2 116.6 . . ? C2 N3 C4 112.2(2) . . ? N3 C4 N9 127.2(2) . . ? N3 C4 C5 126.8(2) . . ? N9 C4 C5 106.0(2) . . ? C4 C5 N7 109.8(2) . . ? C4 C5 C6 118.4(2) . . ? N7 C5 C6 131.4(2) . . ? N6 C6 N1 122.2(2) . . ? N6 C6 C5 123.5(2) . . ? N1 C6 C5 114.2(2) . . ? C6 N6 C9 123.2(2) . . ? C6 N6 H6 118.4 . . ? C9 N6 H6 118.4 . . ? C8 N7 C5 104.61(19) . . ? C8 N7 Zn1 120.56(16) . . ? C5 N7 Zn1 131.93(15) . . ? N7 C8 N9 112.3(2) . . ? N7 C8 H8 123.8 . . ? N9 C8 H8 123.8 . . ? C8 N9 C4 107.34(19) . . ? C8 N9 H9 126.3 . . ? C4 N9 H9 126.3 . . ? N6 C9 C10 108.1(2) . . ? N6 C9 H9A 110.1 . . ? C10 C9 H9A 110.1 . . ? N6 C9 H9B 110.1 . . ? C10 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? C9 C10 C11 112.8(2) . . ? C9 C10 H10A 109.0 . . ? C11 C10 H10A 109.0 . . ? C9 C10 H10B 109.0 . . ? C11 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C13 111.6(2) . . ? C12 C11 C10 108.1(2) . . ? C13 C11 C10 112.5(2) . . ? C12 C11 N1 109.63(19) . . ? C13 C11 N1 107.78(18) . . ? C10 C11 N1 107.21(18) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C2A N1A C6A 121.3(2) . . ? C2A N1A C11A 116.1(2) . . ? C6A N1A C11A 122.5(2) . . ? C2A N1A C11B 127.7(10) . . ? C6A N1A C11B 110.9(10) . . ? N3A C2A N1A 126.6(2) . . ? N3A C2A H2A 116.7 . . ? N1A C2A H2A 116.7 . . ? C2A N3A C4A 112.6(2) . . ? N3A C4A N9A 127.0(2) . . ? N3A C4A C5A 126.5(2) . . ? N9A C4A C5A 106.5(2) . . ? C4A C5A N7A 109.3(2) . . ? C4A C5A C6A 118.7(2) . . ? N7A C5A C6A 131.9(2) . . ? N6A C6A N1A 121.6(2) . . ? N6A C6A C5A 124.2(2) . . ? N1A C6A C5A 114.2(2) . . ? C6A N6A C9A 122.9(3) . . ? C6A N6A C9B 133.4(12) . . ? C6A N6A H6A 119(2) . . ? C9A N6A H6A 118(2) . . ? C9B N6A H6A 107(3) . . ? C8A N7A C5A 105.0(2) . . ? C8A N7A Zn3 118.01(17) . . ? C5A N7A Zn3 135.43(16) . . ? N7A C8A N9A 112.2(2) . . ? N7A C8A H8A 123.9 . . ? N9A C8A H8A 123.9 . . ? C8A N9A C4A 107.1(2) . . ? C8A N9A H9A1 126.5 . . ? C4A N9A H9A1 126.5 . . ? N6A C9A C10A 109.4(5) . . ? N6A C9A H9A2 109.8 . . ? C10A C9A H9A2 109.8 . . ? N6A C9A H9A3 109.8 . . ? C10A C9A H9A3 109.8 . . ? H9A2 C9A H9A3 108.2 . . ? C11A C10A C9A 111.0(4) . . ? C11A C10A H10C 109.4 . . ? C9A C10A H10C 109.4 . . ? C11A C10A H10D 109.4 . . ? C9A C10A H10D 109.4 . . ? H10C C10A H10D 108.0 . . ? C13A C11A C10A 105.6(4) . . ? C13A C11A N1A 110.4(4) . . ? C10A C11A N1A 106.4(4) . . ? C13A C11A C12A 110.9(5) . . ? C10A C11A C12A 114.2(4) . . ? N1A C11A C12A 109.2(4) . . ? N6A C9B C10B 96(2) . . ? N6A C9B H9B1 112.6 . . ? C10B C9B H9B1 112.6 . . ? N6A C9B H9B2 112.6 . . ? C10B C9B H9B2 112.6 . . ? H9B1 C9B H9B2 110.1 . . ? C11B C10B C9B 109(3) . . ? C11B C10B H10E 109.9 . . ? C9B C10B H10E 109.9 . . ? C11B C10B H10F 109.9 . . ? C9B C10B H10F 109.9 . . ? H10E C10B H10F 108.3 . . ? C13B C11B C10B 104(2) . . ? C13B C11B N1A 98.8(19) . . ? C10B C11B N1A 108(2) . . ? C13B C11B C12B 114(2) . . ? C10B C11B C12B 122(2) . . ? N1A C11B C12B 107(2) . . ? C11B C12B H12G 109.5 . . ? C11B C12B H12H 109.5 . . ? H12G C12B H12H 109.5 . . ? C11B C12B H12I 109.5 . . ? H12G C12B H12I 109.5 . . ? H12H C12B H12I 109.5 . . ? C11B C13B H13G 109.5 . . ? C11B C13B H13H 109.5 . . ? H13G C13B H13H 109.5 . . ? C11B C13B H13I 109.5 . . ? H13G C13B H13I 109.5 . . ? H13H C13B H13I 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.664 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.127 # Attachment 'deposit-compound3.cif' data_Travnicek3 _database_code_depnum_ccdc_archive 'CCDC 809165' #TrackingRef 'deposit-compound3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H17 N5, 2(H2 O), 2(Cl) ' _chemical_formula_sum 'C9 H21 Cl2 N5 O2' _chemical_formula_weight 302.21 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn ' 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 7.0591(4) _cell_length_b 15.6552(7) _cell_length_c 13.2731(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.240(5) _cell_angle_gamma 90.00 _cell_volume 1451.69(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5643 _cell_measurement_theta_min 2.7055 _cell_measurement_theta_max 28.683 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.451 _exptl_absorpt_correction_T_min 0.88163 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'Enhance (Oxford Diffraction)' _diffrn_measurement_device_type 'Kuma KM4 + CCD' _diffrn_measurement_method 'rotation method, \w--scan' _diffrn_detector_area_resol_mean 8.3611 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7984 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2562 _reflns_number_gt 2434 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.8000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2562 _refine_ls_number_parameters 183 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0278 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0684 _refine_ls_wR_factor_gt 0.0674 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.085 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl2 Cl 0.15064(5) 0.63882(2) 0.13284(2) 0.01550(11) Uani 1 1 d . . . N1 N 0.60433(17) 0.65272(8) 0.04975(9) 0.0135(3) Uani 1 1 d . . . H1 H 0.5537 0.7007 0.0679 0.016 Uiso 1 1 calc R . . C2 C 0.6166(2) 0.62948(10) -0.04408(11) 0.0156(3) Uani 1 1 d . . . H2 H 0.5735 0.6619 -0.1035 0.019 Uiso 1 1 calc R . . N3 N 0.70034(17) 0.55233(8) -0.04230(9) 0.0143(3) Uani 1 1 d . . . H3 H 0.7222 0.5234 -0.0963 0.017 Uiso 1 1 calc R . . C4 C 0.74694(19) 0.52530(9) 0.05716(10) 0.0128(3) Uani 1 1 d . . . C5 C 0.68433(19) 0.58924(9) 0.11607(10) 0.0121(3) Uani 1 1 d . . . N6 N 0.8271(2) 0.44848(9) 0.08116(11) 0.0188(3) Uani 1 1 d . . . H6A H 0.851(3) 0.4185(12) 0.0307(15) 0.023 Uiso 1 1 d . . . H6B H 0.900(3) 0.4427(12) 0.1379(15) 0.023 Uiso 1 1 d . . . C7 C 0.6959(2) 0.59492(9) 0.22605(10) 0.0115(3) Uani 1 1 d . . . N8 N 0.55344(17) 0.62811(8) 0.26681(9) 0.0129(3) Uani 1 1 d . . . H8 H 0.4482 0.6432 0.2270 0.016 Uiso 1 1 calc R . . C9 C 0.5660(2) 0.64068(9) 0.37844(10) 0.0152(3) Uani 1 1 d . . . C10 C 0.6755(2) 0.56371(10) 0.42836(11) 0.0175(3) Uani 1 1 d . . . H10A H 0.6923 0.5704 0.5033 0.021 Uiso 1 1 calc R . . H10B H 0.6002 0.5111 0.4107 0.021 Uiso 1 1 calc R . . C11 C 0.8704(2) 0.55498(11) 0.39353(11) 0.0208(3) Uani 1 1 d . . . H11A H 0.9580 0.5993 0.4267 0.025 Uiso 1 1 calc R . . H11B H 0.9255 0.4983 0.4136 0.025 Uiso 1 1 calc R . . N12 N 0.85147(17) 0.56451(8) 0.28234(9) 0.0164(3) Uani 1 1 d . . . H12 H 0.9486 0.5492 0.2516 0.020 Uiso 1 1 calc R . . C13 C 0.3618(2) 0.64210(12) 0.40431(12) 0.0252(4) Uani 1 1 d . . . H13A H 0.2900 0.6886 0.3671 0.038 Uiso 1 1 calc R . . H13B H 0.3655 0.6510 0.4776 0.038 Uiso 1 1 calc R . . H13C H 0.2990 0.5875 0.3848 0.038 Uiso 1 1 calc R . . C14 C 0.6683(3) 0.72480(11) 0.40630(12) 0.0269(4) Uani 1 1 d . . . H14A H 0.7943 0.7239 0.3835 0.040 Uiso 1 1 calc R . . H14B H 0.6841 0.7326 0.4803 0.040 Uiso 1 1 calc R . . H14C H 0.5924 0.7720 0.3731 0.040 Uiso 1 1 calc R . . O1 O 0.57695(17) 0.81401(7) 0.11232(9) 0.0222(2) Uani 1 1 d D . . H1V H 0.498(3) 0.8367(12) 0.1506(13) 0.027 Uiso 1 1 d D . . H1W H 0.689(2) 0.8196(12) 0.1484(13) 0.027 Uiso 1 1 d D . . Cl1 Cl 0.30313(5) 0.92445(2) 0.23072(3) 0.01835(11) Uani 1 1 d . . . O2 O 0.94892(17) 0.80141(8) 0.21352(10) 0.0276(3) Uani 1 1 d D . . H2V H 1.039(3) 0.8396(12) 0.2121(15) 0.033 Uiso 1 1 d D . . H2W H 1.000(3) 0.7541(11) 0.1912(15) 0.033 Uiso 1 1 d 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 Cl2 0.01444(19) 0.01859(19) 0.01324(18) -0.00007(13) 0.00113(13) -0.00073(13) N1 0.0132(6) 0.0136(6) 0.0136(6) 0.0002(5) 0.0021(5) 0.0019(5) C2 0.0146(7) 0.0198(8) 0.0122(7) 0.0015(6) 0.0010(6) -0.0013(6) N3 0.0139(6) 0.0196(6) 0.0093(6) -0.0038(5) 0.0018(5) -0.0007(5) C4 0.0094(7) 0.0167(7) 0.0121(6) -0.0019(6) 0.0004(5) -0.0029(5) C5 0.0095(6) 0.0148(7) 0.0118(7) -0.0003(5) 0.0006(5) -0.0009(5) N6 0.0225(7) 0.0180(7) 0.0147(6) -0.0048(5) -0.0011(5) 0.0062(5) C7 0.0125(7) 0.0101(7) 0.0118(7) -0.0019(5) 0.0011(5) -0.0028(5) N8 0.0127(6) 0.0158(6) 0.0099(6) -0.0009(5) 0.0002(5) 0.0022(5) C9 0.0168(7) 0.0191(8) 0.0101(7) -0.0030(6) 0.0032(5) 0.0002(6) C10 0.0205(8) 0.0216(8) 0.0103(7) 0.0006(6) 0.0021(6) 0.0001(6) C11 0.0197(8) 0.0314(9) 0.0105(7) 0.0001(6) -0.0009(6) 0.0065(7) N12 0.0129(6) 0.0254(7) 0.0109(6) -0.0016(5) 0.0015(5) 0.0047(5) C13 0.0195(8) 0.0405(10) 0.0169(8) -0.0034(7) 0.0070(6) 0.0064(7) C14 0.0394(10) 0.0205(8) 0.0210(8) -0.0084(7) 0.0042(7) -0.0053(7) O1 0.0232(6) 0.0197(6) 0.0238(6) -0.0039(5) 0.0040(5) 0.0032(5) Cl1 0.0196(2) 0.0206(2) 0.01519(19) -0.00368(14) 0.00351(14) -0.00535(14) O2 0.0199(6) 0.0233(6) 0.0410(7) -0.0100(5) 0.0088(5) -0.0047(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 N1 C2 1.3123(19) . ? N1 C5 1.3925(18) . ? N1 H1 0.8800 . ? C2 N3 1.343(2) . ? C2 H2 0.9500 . ? N3 C4 1.3804(18) . ? N3 H3 0.8800 . ? C4 N6 1.348(2) . ? C4 C5 1.381(2) . ? C5 C7 1.4531(19) . ? N6 H6A 0.85(2) . ? N6 H6B 0.85(2) . ? C7 N8 1.3151(19) . ? C7 N12 1.3251(19) . ? N8 C9 1.4846(18) . ? N8 H8 0.8800 . ? C9 C14 1.522(2) . ? C9 C13 1.529(2) . ? C9 C10 1.530(2) . ? C10 C11 1.519(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N12 1.4704(18) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? N12 H12 0.8800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? O1 H1V 0.879(15) . ? O1 H1W 0.868(15) . ? O2 H2V 0.878(15) . ? O2 H2W 0.892(15) . ? 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 C2 N1 C5 109.03(12) . . ? C2 N1 H1 125.5 . . ? C5 N1 H1 125.5 . . ? N1 C2 N3 108.74(12) . . ? N1 C2 H2 125.6 . . ? N3 C2 H2 125.6 . . ? C2 N3 C4 109.66(12) . . ? C2 N3 H3 125.2 . . ? C4 N3 H3 125.2 . . ? N6 C4 N3 122.28(13) . . ? N6 C4 C5 132.10(13) . . ? N3 C4 C5 105.52(12) . . ? C4 C5 N1 107.04(12) . . ? C4 C5 C7 129.55(13) . . ? N1 C5 C7 123.41(12) . . ? C4 N6 H6A 115.3(12) . . ? C4 N6 H6B 118.9(12) . . ? H6A N6 H6B 118.2(17) . . ? N8 C7 N12 122.06(12) . . ? N8 C7 C5 120.09(12) . . ? N12 C7 C5 117.84(12) . . ? C7 N8 C9 121.54(12) . . ? C7 N8 H8 119.2 . . ? C9 N8 H8 119.2 . . ? N8 C9 C14 108.40(12) . . ? N8 C9 C13 107.62(12) . . ? C14 C9 C13 111.26(13) . . ? N8 C9 C10 106.38(11) . . ? C14 C9 C10 112.55(13) . . ? C13 C9 C10 110.36(13) . . ? C11 C10 C9 111.23(12) . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10B 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? N12 C11 C10 109.91(12) . . ? N12 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? N12 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C7 N12 C11 123.43(12) . . ? C7 N12 H12 118.3 . . ? C11 N12 H12 118.3 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? H1V O1 H1W 103.9(17) . . ? H2V O2 H2W 103.3(18) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.255 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.047 # Attachment 'deposit-compound4.cif' data_Travnicek4 _database_code_depnum_ccdc_archive 'CCDC 809166' #TrackingRef 'deposit-compound4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H17 N5, Cl4 Cu ' _chemical_formula_sum 'C9 H17 Cl4 Cu N5' _chemical_formula_weight 400.62 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6673(4) _cell_length_b 7.8804(5) _cell_length_c 13.4349(7) _cell_angle_alpha 101.599(5) _cell_angle_beta 91.479(4) _cell_angle_gamma 91.095(5) _cell_volume 794.67(8) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3506 _cell_measurement_theta_min 2.673 _cell_measurement_theta_max 28.3765 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 406 _exptl_absorpt_coefficient_mu 2.040 _exptl_absorpt_correction_T_min 0.84786 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'Enhance (Oxford Diffraction)' _diffrn_measurement_device_type 'Kuma KM4 + CCD' _diffrn_measurement_method 'rotation method, \w--scan' _diffrn_detector_area_resol_mean 8.3611 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4809 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.70 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2778 _reflns_number_gt 2646 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0540P)^2^+0.7000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2778 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.23245(4) 1.04803(4) 0.72628(2) 0.02680(13) Uani 1 1 d . . . Cl1 Cl 0.51565(9) 1.00297(10) 0.68452(6) 0.0407(2) Uani 1 1 d . . . Cl2 Cl 0.26191(12) 1.33084(10) 0.78369(7) 0.0492(2) Uani 1 1 d . . . Cl3 Cl -0.02963(9) 1.06323(9) 0.64577(7) 0.0413(2) Uani 1 1 d . . . Cl4 Cl 0.18058(10) 0.78241(9) 0.75591(6) 0.0392(2) Uani 1 1 d . . . C1 C 0.2537(3) 0.4449(3) 0.27690(19) 0.0258(5) Uani 1 1 d . . . N2 N 0.2984(3) 0.3012(3) 0.21568(17) 0.0299(5) Uani 1 1 d . . . H2 H 0.3390 0.2175 0.2436 0.036 Uiso 1 1 calc R . . C3 C 0.2854(4) 0.2698(4) 0.1030(2) 0.0336(6) Uani 1 1 d . . . C4 C 0.1681(5) 0.4090(5) 0.0748(2) 0.0482(8) Uani 1 1 d . . . H4A H 0.1760 0.4076 0.0012 0.058 Uiso 1 1 calc R . . H4B H 0.0453 0.3822 0.0884 0.058 Uiso 1 1 calc R . . C5 C 0.2195(5) 0.5876(5) 0.1345(3) 0.0503(9) Uani 1 1 d . . . H5A H 0.3385 0.6200 0.1169 0.060 Uiso 1 1 calc R . . H5B H 0.1376 0.6741 0.1177 0.060 Uiso 1 1 calc R . . N6 N 0.2143(3) 0.5848(3) 0.24236(18) 0.0341(5) Uani 1 1 d . . . H6 H 0.1843 0.6785 0.2854 0.041 Uiso 1 1 calc R . . C7 C 0.2481(3) 0.4515(3) 0.3856(2) 0.0275(5) Uani 1 1 d . . . C8 C 0.2957(4) 0.5819(4) 0.4670(2) 0.0302(6) Uani 1 1 d . . . N9 N 0.2555(3) 0.5195(3) 0.55242(18) 0.0364(6) Uani 1 1 d . . . H9 H 0.2718 0.5769 0.6154 0.044 Uiso 1 1 calc R . . C10 C 0.1883(4) 0.3593(4) 0.5255(2) 0.0404(7) Uani 1 1 d . . . H10 H 0.1506 0.2891 0.5710 0.048 Uiso 1 1 calc R . . N11 N 0.1827(3) 0.3144(3) 0.42665(19) 0.0340(5) Uani 1 1 d . . . H11 H 0.1439 0.2138 0.3913 0.041 Uiso 1 1 calc R . . C12 C 0.2059(5) 0.0886(5) 0.0673(3) 0.0583(10) Uani 1 1 d . . . H12A H 0.2806 0.0041 0.0908 0.087 Uiso 1 1 calc R . . H12B H 0.1963 0.0618 -0.0071 0.087 Uiso 1 1 calc R . . H12C H 0.0896 0.0833 0.0953 0.087 Uiso 1 1 calc R . . C13 C 0.4681(4) 0.2791(5) 0.0616(3) 0.0471(8) Uani 1 1 d . . . H13A H 0.5205 0.3944 0.0877 0.071 Uiso 1 1 calc R . . H13B H 0.4606 0.2575 -0.0128 0.071 Uiso 1 1 calc R . . H13C H 0.5405 0.1913 0.0834 0.071 Uiso 1 1 calc R . . N14 N 0.3721(4) 0.7378(4) 0.4727(3) 0.0494(7) Uani 1 1 d . . . H14A H 0.398(6) 0.770(6) 0.416(3) 0.059 Uiso 1 1 d . . . H14B H 0.399(6) 0.799(6) 0.528(3) 0.059 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 Cu1 0.0279(2) 0.01946(19) 0.0321(2) 0.00270(13) 0.00152(13) 0.00055(13) Cl1 0.0278(4) 0.0388(4) 0.0580(5) 0.0150(3) 0.0072(3) 0.0032(3) Cl2 0.0613(5) 0.0238(4) 0.0554(5) -0.0066(3) -0.0121(4) -0.0017(3) Cl3 0.0291(4) 0.0260(3) 0.0653(5) 0.0022(3) -0.0079(3) 0.0008(3) Cl4 0.0515(4) 0.0247(3) 0.0429(4) 0.0101(3) 0.0066(3) -0.0015(3) C1 0.0254(13) 0.0229(13) 0.0281(14) 0.0032(11) 0.0016(10) 0.0004(10) N2 0.0371(12) 0.0238(11) 0.0275(12) 0.0016(9) 0.0000(9) 0.0065(9) C3 0.0344(15) 0.0376(16) 0.0244(14) -0.0040(11) -0.0016(11) 0.0033(12) C4 0.0473(19) 0.069(2) 0.0287(16) 0.0096(15) -0.0027(13) 0.0194(17) C5 0.070(2) 0.0475(19) 0.0402(18) 0.0221(15) 0.0110(16) 0.0245(17) N6 0.0449(14) 0.0249(11) 0.0334(13) 0.0067(9) 0.0062(10) 0.0095(10) C7 0.0315(14) 0.0231(13) 0.0279(14) 0.0051(10) 0.0030(10) -0.0008(11) C8 0.0327(14) 0.0267(13) 0.0298(14) 0.0023(11) 0.0005(11) 0.0027(11) N9 0.0418(14) 0.0423(14) 0.0238(12) 0.0032(10) 0.0013(10) 0.0043(11) C10 0.0431(17) 0.0450(18) 0.0378(17) 0.0187(14) 0.0074(13) 0.0007(14) N11 0.0374(13) 0.0246(12) 0.0401(14) 0.0072(10) 0.0036(10) -0.0042(10) C12 0.060(2) 0.057(2) 0.045(2) -0.0177(17) 0.0042(16) -0.0108(18) C13 0.0383(17) 0.060(2) 0.0396(17) 0.0016(15) 0.0063(13) 0.0055(15) N14 0.070(2) 0.0291(14) 0.0448(17) -0.0011(12) -0.0067(15) -0.0126(13) _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 Cu1 Cl2 2.2121(8) . ? Cu1 Cl4 2.2382(7) . ? Cu1 Cl1 2.2733(8) . ? Cu1 Cl3 2.2741(8) . ? C1 N2 1.316(3) . ? C1 N6 1.316(3) . ? C1 C7 1.453(4) . ? N2 C3 1.485(4) . ? N2 H2 0.8800 . ? C3 C12 1.522(5) . ? C3 C13 1.526(4) . ? C3 C4 1.530(4) . ? C4 C5 1.513(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N6 1.455(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? N6 H6 0.8800 . ? C7 C8 1.378(4) . ? C7 N11 1.398(3) . ? C8 N14 1.338(4) . ? C8 N9 1.376(4) . ? N9 C10 1.331(4) . ? N9 H9 0.8800 . ? C10 N11 1.304(4) . ? C10 H10 0.9500 . ? N11 H11 0.8800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? N14 H14A 0.88(5) . ? N14 H14B 0.82(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl2 Cu1 Cl4 149.59(3) . . ? Cl2 Cu1 Cl1 96.37(3) . . ? Cl4 Cu1 Cl1 95.59(3) . . ? Cl2 Cu1 Cl3 94.83(3) . . ? Cl4 Cu1 Cl3 94.70(3) . . ? Cl1 Cu1 Cl3 138.13(3) . . ? N2 C1 N6 121.7(2) . . ? N2 C1 C7 119.7(2) . . ? N6 C1 C7 118.6(2) . . ? C1 N2 C3 124.9(2) . . ? C1 N2 H2 117.6 . . ? C3 N2 H2 117.6 . . ? N2 C3 C12 106.7(3) . . ? N2 C3 C13 109.0(2) . . ? C12 C3 C13 110.1(3) . . ? N2 C3 C4 107.1(2) . . ? C12 C3 C4 111.9(3) . . ? C13 C3 C4 111.9(3) . . ? C5 C4 C3 111.7(3) . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? N6 C5 C4 108.4(3) . . ? N6 C5 H5A 110.0 . . ? C4 C5 H5A 110.0 . . ? N6 C5 H5B 110.0 . . ? C4 C5 H5B 110.0 . . ? H5A C5 H5B 108.4 . . ? C1 N6 C5 121.3(2) . . ? C1 N6 H6 119.3 . . ? C5 N6 H6 119.3 . . ? C8 C7 N11 106.3(2) . . ? C8 C7 C1 130.8(2) . . ? N11 C7 C1 122.8(2) . . ? N14 C8 N9 122.0(3) . . ? N14 C8 C7 132.1(3) . . ? N9 C8 C7 105.8(2) . . ? C10 N9 C8 109.8(2) . . ? C10 N9 H9 125.1 . . ? C8 N9 H9 125.1 . . ? N11 C10 N9 108.9(3) . . ? N11 C10 H10 125.5 . . ? N9 C10 H10 125.5 . . ? C10 N11 C7 109.2(2) . . ? C10 N11 H11 125.4 . . ? C7 N11 H11 125.4 . . ? C3 C12 H12A 109.5 . . ? C3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C3 C13 H13A 109.5 . . ? C3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C8 N14 H14A 118(3) . . ? C8 N14 H14B 121(3) . . ? H14A N14 H14B 121(4) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.503 _refine_diff_density_min -0.706 _refine_diff_density_rms 0.091 # Attachment 'deposit-compound5.cif' data_Travnicek5 _database_code_depnum_ccdc_archive 'CCDC 809167' #TrackingRef 'deposit-compound5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H17 N5, Cl4 Zn ' _chemical_formula_sum 'C9 H17 Cl4 N5 Zn' _chemical_formula_weight 402.45 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' 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8356(4) _cell_length_b 13.1475(6) _cell_length_c 15.8482(9) _cell_angle_alpha 76.546(4) _cell_angle_beta 84.994(4) _cell_angle_gamma 81.751(4) _cell_volume 1568.96(14) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5950 _cell_measurement_theta_min 2.379 _cell_measurement_theta_max 28.828 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.704 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 2.239 _exptl_absorpt_correction_T_min 0.52964 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'Enhance (Oxford Diffraction)' _diffrn_measurement_device_type 'Kuma KM4 + CCD' _diffrn_measurement_method 'rotation method, \w--scan' _diffrn_detector_area_resol_mean 8.3611 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9645 _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5487 _reflns_number_gt 5015 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.7500P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5487 _refine_ls_number_parameters 359 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1100 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.19169(4) 0.24003(2) 0.71401(2) 0.01381(12) Uani 1 1 d . . . Zn2 Zn 0.19216(4) 0.72839(2) 0.70745(2) 0.01274(12) Uani 1 1 d . . . Cl3 Cl 0.22021(11) 0.20267(6) 0.57982(5) 0.02378(19) Uani 1 1 d . . . Cl4 Cl 0.39595(10) 0.68249(5) 0.60582(4) 0.01870(17) Uani 1 1 d . . . Cl5 Cl 0.18974(9) 0.42102(5) 0.69114(4) 0.01287(16) Uani 1 1 d . . . Cl6 Cl 0.24647(11) 0.63960(6) 0.84218(4) 0.02191(18) Uani 1 1 d . . . Cl7 Cl -0.06611(10) 0.19439(5) 0.77283(5) 0.01916(18) Uani 1 1 d . . . Cl8 Cl -0.07749(10) 0.72482(6) 0.66712(6) 0.0275(2) Uani 1 1 d . . . Cl9 Cl 0.20491(9) 0.90769(5) 0.69484(4) 0.01366(16) Uani 1 1 d . . . Cl10 Cl 0.41664(11) 0.16419(6) 0.79385(5) 0.0272(2) Uani 1 1 d . . . N1 N 0.1569(3) 0.91819(18) 0.37214(15) 0.0144(5) Uani 1 1 d . . . H1 H 0.1074 0.8872 0.3389 0.017 Uiso 1 1 calc R . . C2 C 0.1440(4) 0.8959(2) 0.45723(19) 0.0169(6) Uani 1 1 d . . . H2 H 0.0814 0.8435 0.4929 0.020 Uiso 1 1 calc R . . N3 N 0.2337(3) 0.95920(19) 0.48530(16) 0.0160(5) Uani 1 1 d . . . H3 H 0.2438 0.9590 0.5402 0.019 Uiso 1 1 calc R . . C4 C 0.3080(4) 1.0249(2) 0.41574(18) 0.0138(6) Uani 1 1 d . . . C5 C 0.2605(4) 0.9982(2) 0.34229(18) 0.0135(6) Uani 1 1 d . . . N6 N 0.4102(3) 1.0952(2) 0.42638(18) 0.0154(5) Uani 1 1 d . . . H6A H 0.384(5) 1.119(3) 0.473(2) 0.018 Uiso 1 1 d . . . H6B H 0.425(5) 1.141(3) 0.385(2) 0.018 Uiso 1 1 d . . . C7 C 0.2883(4) 1.0462(2) 0.25098(18) 0.0128(6) Uani 1 1 d . . . N8 N 0.4310(3) 1.0904(2) 0.22410(16) 0.0177(5) Uani 1 1 d . . . H8 H 0.5090 1.0862 0.2619 0.021 Uiso 1 1 calc R . . C9 C 0.4643(5) 1.1462(3) 0.1338(2) 0.0262(7) Uani 1 1 d . . . H9A H 0.5427 1.0994 0.1026 0.031 Uiso 1 1 calc R . . H9B H 0.5210 1.2091 0.1327 0.031 Uiso 1 1 calc R . . C10 C 0.2950(5) 1.1796(3) 0.0890(2) 0.0235(7) Uani 1 1 d . . . H10A H 0.3196 1.2071 0.0261 0.028 Uiso 1 1 calc R . . H10B H 0.2271 1.2372 0.1128 0.028 Uiso 1 1 calc R . . C11 C 0.1884(4) 1.0882(2) 0.10144(18) 0.0150(6) Uani 1 1 d . . . N12 N 0.1693(3) 1.04639(19) 0.19695(15) 0.0136(5) Uani 1 1 d . . . H12 H 0.0733 1.0204 0.2186 0.016 Uiso 1 1 calc R . . C13 C 0.0070(4) 1.1258(3) 0.0702(2) 0.0227(7) Uani 1 1 d . . . H13A H -0.0625 1.0672 0.0861 0.034 Uiso 1 1 calc R . . H13B H 0.0131 1.1513 0.0069 0.034 Uiso 1 1 calc R . . H13C H -0.0464 1.1831 0.0975 0.034 Uiso 1 1 calc R . . C14 C 0.2759(4) 1.0012(2) 0.05720(19) 0.0196(7) Uani 1 1 d . . . H14A H 0.3881 0.9730 0.0818 0.029 Uiso 1 1 calc R . . H14B H 0.2931 1.0302 -0.0053 0.029 Uiso 1 1 calc R . . H14C H 0.2028 0.9445 0.0667 0.029 Uiso 1 1 calc R . . N1' N 0.2067(3) 0.46073(18) 0.39435(15) 0.0130(5) Uani 1 1 d . . . H1' H 0.1635 0.4138 0.3738 0.016 Uiso 1 1 calc R . . C2' C 0.2070(4) 0.4619(2) 0.47646(19) 0.0176(6) Uani 1 1 d . . . H2' H 0.1629 0.4119 0.5237 0.021 Uiso 1 1 calc R . . N3' N 0.2800(3) 0.54555(19) 0.48276(15) 0.0163(5) Uani 1 1 d . . . H3' H 0.2939 0.5633 0.5317 0.020 Uiso 1 1 calc R . . C4' C 0.3301(4) 0.5998(2) 0.40121(18) 0.0135(6) Uani 1 1 d . . . C5' C 0.2855(4) 0.5451(2) 0.34425(18) 0.0121(6) Uani 1 1 d . . . N6' N 0.3979(4) 0.6908(2) 0.38878(19) 0.0187(6) Uani 1 1 d . . . H6'A H 0.425(5) 0.717(3) 0.341(2) 0.022 Uiso 1 1 d . . . H6'B H 0.427(5) 0.704(3) 0.432(2) 0.022 Uiso 1 1 d . . . C7' C 0.3080(4) 0.5630(2) 0.24993(18) 0.0118(6) Uani 1 1 d . . . N8' N 0.4561(3) 0.5917(2) 0.21259(16) 0.0158(5) Uani 1 1 d . . . H8' H 0.5396 0.5928 0.2459 0.019 Uiso 1 1 calc R . . C9' C 0.4879(4) 0.6215(3) 0.11842(19) 0.0190(6) Uani 1 1 d . . . H9'1 H 0.5562 0.5620 0.0974 0.023 Uiso 1 1 calc R . . H9'2 H 0.5549 0.6823 0.1032 0.023 Uiso 1 1 calc R . . C10' C 0.3158(4) 0.6509(2) 0.07489(18) 0.0163(6) Uani 1 1 d . . . H10C H 0.3370 0.6588 0.0113 0.020 Uiso 1 1 calc R . . H10D H 0.2598 0.7195 0.0856 0.020 Uiso 1 1 calc R . . C11' C 0.1949(4) 0.5670(2) 0.10961(18) 0.0143(6) Uani 1 1 d . . . N12' N 0.1827(3) 0.55032(18) 0.20522(15) 0.0118(5) Uani 1 1 d . . . H12' H 0.0867 0.5309 0.2335 0.014 Uiso 1 1 calc R . . C13' C 0.0143(4) 0.6054(2) 0.0779(2) 0.0195(7) Uani 1 1 d . . . H13D H -0.0618 0.5517 0.1025 0.029 Uiso 1 1 calc R . . H13E H 0.0187 0.6186 0.0143 0.029 Uiso 1 1 calc R . . H13F H -0.0304 0.6709 0.0963 0.029 Uiso 1 1 calc R . . C14' C 0.2640(4) 0.4620(2) 0.0855(2) 0.0223(7) Uani 1 1 d . . . H14D H 0.3792 0.4375 0.1076 0.033 Uiso 1 1 calc R . . H14E H 0.2710 0.4716 0.0222 0.033 Uiso 1 1 calc R . . H14F H 0.1860 0.4097 0.1114 0.033 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 0.0139(2) 0.00987(19) 0.0172(2) -0.00207(14) -0.00251(14) -0.00038(14) Zn2 0.0126(2) 0.01005(19) 0.01497(19) -0.00161(13) -0.00461(14) 0.00075(14) Cl3 0.0339(5) 0.0188(4) 0.0210(4) -0.0089(3) 0.0050(3) -0.0079(3) Cl4 0.0209(4) 0.0162(4) 0.0201(4) -0.0079(3) 0.0009(3) -0.0008(3) Cl5 0.0119(3) 0.0092(3) 0.0169(3) -0.0021(3) -0.0024(3) 0.0004(3) Cl6 0.0301(4) 0.0164(4) 0.0166(4) 0.0008(3) -0.0062(3) 0.0015(3) Cl7 0.0198(4) 0.0153(4) 0.0247(4) -0.0087(3) 0.0042(3) -0.0066(3) Cl8 0.0179(4) 0.0167(4) 0.0516(5) -0.0113(3) -0.0187(4) 0.0019(3) Cl9 0.0128(4) 0.0100(3) 0.0179(3) -0.0031(3) -0.0020(3) 0.0004(3) Cl10 0.0251(4) 0.0149(4) 0.0387(4) 0.0019(3) -0.0171(3) 0.0032(3) N1 0.0143(13) 0.0100(11) 0.0186(12) -0.0017(9) -0.0063(10) -0.0003(10) C2 0.0140(15) 0.0115(14) 0.0229(15) 0.0007(12) -0.0056(12) 0.0014(12) N3 0.0167(14) 0.0155(12) 0.0147(12) -0.0010(10) -0.0043(10) -0.0005(10) C4 0.0125(14) 0.0098(13) 0.0180(14) -0.0037(11) -0.0033(11) 0.0046(11) C5 0.0128(15) 0.0078(13) 0.0190(14) -0.0029(11) -0.0038(11) 0.0032(11) N6 0.0133(13) 0.0177(13) 0.0162(13) -0.0050(11) -0.0028(10) -0.0020(10) C7 0.0125(15) 0.0086(13) 0.0173(14) -0.0061(11) -0.0029(11) 0.0055(11) N8 0.0138(13) 0.0198(13) 0.0210(13) -0.0041(10) -0.0053(10) -0.0055(11) C9 0.0277(19) 0.0303(18) 0.0223(16) -0.0023(14) -0.0024(14) -0.0149(15) C10 0.0331(19) 0.0152(15) 0.0210(16) 0.0041(12) -0.0054(13) -0.0096(14) C11 0.0161(16) 0.0140(14) 0.0139(14) 0.0004(11) -0.0061(11) -0.0011(12) N12 0.0141(13) 0.0123(12) 0.0137(12) 0.0001(9) -0.0032(10) -0.0026(10) C13 0.0211(17) 0.0230(16) 0.0211(16) -0.0018(13) -0.0087(13) 0.0057(13) C14 0.0209(17) 0.0202(16) 0.0172(14) -0.0042(12) -0.0031(12) 0.0007(13) N1' 0.0117(12) 0.0093(11) 0.0166(12) 0.0001(9) -0.0041(9) 0.0007(9) C2' 0.0155(16) 0.0155(15) 0.0185(15) 0.0013(12) -0.0031(12) 0.0016(12) N3' 0.0174(13) 0.0172(13) 0.0146(12) -0.0050(10) -0.0055(10) 0.0023(10) C4' 0.0100(14) 0.0100(13) 0.0187(14) -0.0022(11) -0.0047(11) 0.0058(11) C5' 0.0104(14) 0.0099(13) 0.0148(13) -0.0013(11) -0.0048(11) 0.0032(11) N6' 0.0213(15) 0.0183(14) 0.0191(13) -0.0080(11) -0.0017(11) -0.0042(11) C7' 0.0111(14) 0.0061(13) 0.0174(14) -0.0032(10) -0.0030(11) 0.0039(11) N8' 0.0127(13) 0.0191(13) 0.0161(12) -0.0033(10) -0.0039(10) -0.0026(10) C9' 0.0151(16) 0.0255(16) 0.0173(15) -0.0056(12) -0.0004(12) -0.0044(13) C10' 0.0168(16) 0.0162(15) 0.0147(14) -0.0008(11) -0.0021(12) -0.0024(12) C11' 0.0152(15) 0.0140(14) 0.0137(14) -0.0033(11) -0.0043(11) 0.0004(12) N12' 0.0106(12) 0.0101(11) 0.0148(12) -0.0027(9) -0.0009(9) -0.0012(9) C13' 0.0151(16) 0.0225(16) 0.0197(15) -0.0007(12) -0.0078(12) -0.0010(13) C14' 0.0264(18) 0.0176(16) 0.0255(16) -0.0104(13) -0.0050(14) 0.0003(13) _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 Cl10 2.2360(8) . ? Zn1 Cl7 2.2513(8) . ? Zn1 Cl3 2.2773(8) . ? Zn1 Cl5 2.3202(7) . ? Zn2 Cl6 2.2270(7) . ? Zn2 Cl8 2.2700(8) . ? Zn2 Cl4 2.2881(8) . ? Zn2 Cl9 2.3349(7) . ? N1 C2 1.310(4) . ? N1 C5 1.391(4) . ? N1 H1 0.8800 . ? C2 N3 1.334(4) . ? C2 H2 0.9500 . ? N3 C4 1.374(4) . ? N3 H3 0.8800 . ? C4 N6 1.354(4) . ? C4 C5 1.386(4) . ? C5 C7 1.449(4) . ? N6 H6A 0.86(4) . ? N6 H6B 0.80(4) . ? C7 N12 1.319(4) . ? C7 N8 1.327(4) . ? N8 C9 1.467(4) . ? N8 H8 0.8800 . ? C9 C10 1.519(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.526(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N12 1.488(4) . ? C11 C13 1.522(4) . ? C11 C14 1.528(4) . ? N12 H12 0.8800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? N1' C2' 1.305(4) . ? N1' C5' 1.394(4) . ? N1' H1' 0.8800 . ? C2' N3' 1.337(4) . ? C2' H2' 0.9500 . ? N3' C4' 1.377(4) . ? N3' H3' 0.8800 . ? C4' N6' 1.343(4) . ? C4' C5' 1.373(4) . ? C5' C7' 1.457(4) . ? N6' H6'A 0.78(4) . ? N6' H6'B 0.81(4) . ? C7' N12' 1.311(4) . ? C7' N8' 1.319(4) . ? N8' C9' 1.461(4) . ? N8' H8' 0.8800 . ? C9' C10' 1.528(4) . ? C9' H9'1 0.9900 . ? C9' H9'2 0.9900 . ? C10' C11' 1.531(4) . ? C10' H10C 0.9900 . ? C10' H10D 0.9900 . ? C11' N12' 1.476(4) . ? C11' C13' 1.521(4) . ? C11' C14' 1.529(4) . ? N12' H12' 0.8800 . ? C13' H13D 0.9800 . ? C13' H13E 0.9800 . ? C13' H13F 0.9800 . ? C14' H14D 0.9800 . ? C14' H14E 0.9800 . ? C14' H14F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl10 Zn1 Cl7 114.88(3) . . ? Cl10 Zn1 Cl3 112.12(3) . . ? Cl7 Zn1 Cl3 106.23(3) . . ? Cl10 Zn1 Cl5 107.12(3) . . ? Cl7 Zn1 Cl5 110.09(3) . . ? Cl3 Zn1 Cl5 106.09(3) . . ? Cl6 Zn2 Cl8 114.86(3) . . ? Cl6 Zn2 Cl4 112.91(3) . . ? Cl8 Zn2 Cl4 110.61(3) . . ? Cl6 Zn2 Cl9 109.93(3) . . ? Cl8 Zn2 Cl9 103.38(3) . . ? Cl4 Zn2 Cl9 104.16(3) . . ? C2 N1 C5 109.7(2) . . ? C2 N1 H1 125.1 . . ? C5 N1 H1 125.1 . . ? N1 C2 N3 108.5(3) . . ? N1 C2 H2 125.8 . . ? N3 C2 H2 125.8 . . ? C2 N3 C4 109.9(2) . . ? C2 N3 H3 125.0 . . ? C4 N3 H3 125.0 . . ? N6 C4 N3 121.9(3) . . ? N6 C4 C5 132.2(3) . . ? N3 C4 C5 105.9(2) . . ? C4 C5 N1 106.0(2) . . ? C4 C5 C7 130.7(3) . . ? N1 C5 C7 123.0(3) . . ? C4 N6 H6A 114(2) . . ? C4 N6 H6B 115(3) . . ? H6A N6 H6B 112(3) . . ? N12 C7 N8 121.7(3) . . ? N12 C7 C5 119.1(3) . . ? N8 C7 C5 119.2(3) . . ? C7 N8 C9 122.7(3) . . ? C7 N8 H8 118.7 . . ? C9 N8 H8 118.7 . . ? N8 C9 C10 109.7(3) . . ? N8 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? N8 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C9 C10 C11 111.9(3) . . ? C9 C10 H10A 109.2 . . ? C11 C10 H10A 109.2 . . ? C9 C10 H10B 109.2 . . ? C11 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? N12 C11 C13 106.7(2) . . ? N12 C11 C10 105.7(2) . . ? C13 C11 C10 111.6(3) . . ? N12 C11 C14 110.0(2) . . ? C13 C11 C14 110.2(2) . . ? C10 C11 C14 112.4(3) . . ? C7 N12 C11 123.6(3) . . ? C7 N12 H12 118.2 . . ? C11 N12 H12 118.2 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C2' N1' C5' 109.6(2) . . ? C2' N1' H1' 125.2 . . ? C5' N1' H1' 125.2 . . ? N1' C2' N3' 108.3(3) . . ? N1' C2' H2' 125.8 . . ? N3' C2' H2' 125.8 . . ? C2' N3' C4' 109.9(2) . . ? C2' N3' H3' 125.1 . . ? C4' N3' H3' 125.1 . . ? N6' C4' C5' 132.1(3) . . ? N6' C4' N3' 122.0(3) . . ? C5' C4' N3' 105.8(2) . . ? C4' C5' N1' 106.4(2) . . ? C4' C5' C7' 131.3(3) . . ? N1' C5' C7' 122.3(2) . . ? C4' N6' H6'A 117(3) . . ? C4' N6' H6'B 115(3) . . ? H6'A N6' H6'B 126(4) . . ? N12' C7' N8' 122.3(3) . . ? N12' C7' C5' 119.7(3) . . ? N8' C7' C5' 118.0(3) . . ? C7' N8' C9' 123.0(3) . . ? C7' N8' H8' 118.5 . . ? C9' N8' H8' 118.5 . . ? N8' C9' C10' 109.5(2) . . ? N8' C9' H9'1 109.8 . . ? C10' C9' H9'1 109.8 . . ? N8' C9' H9'2 109.8 . . ? C10' C9' H9'2 109.8 . . ? H9'1 C9' H9'2 108.2 . . ? C9' C10' C11' 111.3(2) . . ? C9' C10' H10C 109.4 . . ? C11' C10' H10C 109.4 . . ? C9' C10' H10D 109.4 . . ? C11' C10' H10D 109.4 . . ? H10C C10' H10D 108.0 . . ? N12' C11' C13' 107.6(2) . . ? N12' C11' C14' 108.6(2) . . ? C13' C11' C14' 110.5(2) . . ? N12' C11' C10' 107.1(2) . . ? C13' C11' C10' 110.8(2) . . ? C14' C11' C10' 112.1(3) . . ? C7' N12' C11' 123.1(2) . . ? C7' N12' H12' 118.5 . . ? C11' N12' H12' 118.5 . . ? C11' C13' H13D 109.5 . . ? C11' C13' H13E 109.5 . . ? H13D C13' H13E 109.5 . . ? C11' C13' H13F 109.5 . . ? H13D C13' H13F 109.5 . . ? H13E C13' H13F 109.5 . . ? C11' C14' H14D 109.5 . . ? C11' C14' H14E 109.5 . . ? H14D C14' H14E 109.5 . . ? C11' C14' H14F 109.5 . . ? H14D C14' H14F 109.5 . . ? H14E C14' H14F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.253 _refine_diff_density_min -1.152 _refine_diff_density_rms 0.132