Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Fabian Mohr' _publ_contact_author_address ; Departamento de Quimica Inorganica Universidad de Zaragoza Facultad de Ciencias Plaza San Francisco s/n Zaragoza 50009 SPAIN ; _publ_contact_author_email FMOHR@UNIZAR.ES _publ_section_title ; Synthesis and coordination chemistry of an alkyne functionalised bis(pyrazolyl)methane ligand. ; loop_ _publ_author_name 'Fabian Mohr' 'Elena Cerrada' 'Mariano Laguna' # Attachment 'ele78as.cif' data_ele78as _database_code_depnum_ccdc_archive 'CCDC 620814' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 Cl2 Co N4 O' _chemical_formula_weight 408.14 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2354(9) _cell_length_b 9.3496(11) _cell_length_c 11.5484(13) _cell_angle_alpha 95.643(2) _cell_angle_beta 97.344(2) _cell_angle_gamma 108.028(2) _cell_volume 829.60(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.128 _exptl_crystal_size_mid 0.106 _exptl_crystal_size_min 0.067 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 414 _exptl_absorpt_coefficient_mu 1.367 _exptl_absorpt_correction_type 'multi-scan correction' _exptl_absorpt_correction_T_min 0.738704 _exptl_absorpt_correction_T_max 0.934472 _exptl_absorpt_process_details ? _exptl_special_details ; (Sheldrick, M. SADABS empirical absorption program, University of Gottingen, 1996) ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area Detector' _diffrn_measurement_method 'Phi and Omega Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7492 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.1009 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 28.25 _reflns_number_total 3851 _reflns_number_gt 2759 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'CIFTAB (Sheldrick, 1197)' _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^)+(0.0220P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3851 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0680 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.0832 _refine_ls_wR_factor_gt 0.0760 _refine_ls_goodness_of_fit_ref 0.864 _refine_ls_restrained_S_all 0.864 _refine_ls_shift/su_max 0.077 _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 Co1 Co 0.15346(6) 0.10666(5) 0.13210(4) 0.01570(13) Uani 1 1 d . . . Cl1 Cl -0.00876(10) 0.18252(10) 0.25410(7) 0.0212(2) Uani 1 1 d . . . Cl2 Cl 0.09757(10) 0.15392(9) -0.06086(7) 0.01731(19) Uani 1 1 d . . . N1 N 0.3101(3) -0.0245(3) 0.1300(2) 0.0153(6) Uani 1 1 d . . . N2 N 0.3810(3) 0.2989(3) 0.1822(2) 0.0152(6) Uani 1 1 d . . . O1 O 0.6633(3) 0.3726(3) 0.46948(19) 0.0258(6) Uani 1 1 d . . . N3 N 0.4757(3) 0.0188(3) 0.1914(2) 0.0133(6) Uani 1 1 d . . . N4 N 0.5367(3) 0.2855(3) 0.2260(2) 0.0148(6) Uani 1 1 d . . . C1 C 0.5632(4) -0.0709(4) 0.1525(3) 0.0153(7) Uani 1 1 d . . . H1 H 0.672(4) -0.056(4) 0.179(3) 0.019(10) Uiso 1 1 d . . . C2 C 0.4534(4) -0.1778(4) 0.0642(3) 0.0165(7) Uani 1 1 d . . . H2 H 0.477(4) -0.254(3) 0.022(3) 0.010(8) Uiso 1 1 d . . . C3 C 0.3007(4) -0.1455(4) 0.0529(3) 0.0160(7) Uani 1 1 d . . . H3 H 0.192(4) -0.198(3) 0.003(3) 0.018(9) Uiso 1 1 d . . . C4 C 0.4218(5) 0.4336(4) 0.1446(3) 0.0179(8) Uani 1 1 d . . . H4 H 0.338(4) 0.471(3) 0.114(2) 0.005(8) Uiso 1 1 d . . . C5 C 0.6007(5) 0.5061(4) 0.1639(3) 0.0192(8) Uani 1 1 d . . . H5 H 0.662(4) 0.596(3) 0.142(2) 0.009(8) Uiso 1 1 d . . . C6 C 0.6687(5) 0.4078(4) 0.2157(3) 0.0180(8) Uani 1 1 d . . . H6 H 0.784(4) 0.403(3) 0.239(3) 0.014(9) Uiso 1 1 d . . . C7 C 0.5433(4) 0.1528(4) 0.2808(3) 0.0145(7) Uani 1 1 d . . . H7 H 0.664(3) 0.165(3) 0.301(2) 0.000(7) Uiso 1 1 d . . . C8 C 0.4507(4) 0.1406(4) 0.3869(3) 0.0156(7) Uani 1 1 d . . . C9 C 0.5157(4) 0.2608(4) 0.4821(3) 0.0196(8) Uani 1 1 d . . . C10 C 0.4306(5) 0.2601(5) 0.5776(3) 0.0255(9) Uani 1 1 d . . . H10 H 0.475(4) 0.342(3) 0.638(3) 0.015(9) Uiso 1 1 d . . . C11 C 0.2830(5) 0.1390(5) 0.5810(3) 0.0266(9) Uani 1 1 d . . . H11 H 0.212(4) 0.137(4) 0.642(3) 0.027(10) Uiso 1 1 d . . . C12 C 0.2249(5) 0.0168(5) 0.4928(3) 0.0253(9) Uani 1 1 d . . . H12 H 0.132(4) -0.067(4) 0.501(3) 0.032(11) Uiso 1 1 d . . . C13 C 0.3094(4) 0.0181(4) 0.3955(3) 0.0203(8) Uani 1 1 d . . . H13 H 0.263(4) -0.069(4) 0.336(3) 0.026(10) Uiso 1 1 d . . . C14 C 0.7551(6) 0.4837(4) 0.5706(3) 0.0294(10) Uani 1 1 d . . . H15 H 0.839(4) 0.556(4) 0.541(3) 0.024(10) Uiso 1 1 d . . . H14 H 0.670(4) 0.526(3) 0.598(3) 0.014(9) Uiso 1 1 d . . . C15 C 0.8356(5) 0.4176(4) 0.6628(3) 0.0273(9) Uani 1 1 d . . . C16 C 0.8992(5) 0.3647(5) 0.7366(4) 0.0349(10) Uani 1 1 d . . . H16 H 0.941(5) 0.322(5) 0.790(4) 0.059(15) 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 Co1 0.0148(3) 0.0182(3) 0.0136(2) 0.00115(19) 0.00126(19) 0.0055(2) Cl1 0.0161(4) 0.0245(5) 0.0197(4) -0.0040(4) 0.0032(3) 0.0039(4) Cl2 0.0152(4) 0.0191(4) 0.0154(4) 0.0023(3) 0.0004(3) 0.0034(3) N1 0.0106(14) 0.0202(16) 0.0110(14) 0.0007(12) -0.0014(11) 0.0011(12) N2 0.0136(15) 0.0168(15) 0.0142(15) -0.0015(12) 0.0019(12) 0.0050(12) O1 0.0311(15) 0.0213(14) 0.0144(13) -0.0032(11) -0.0038(11) -0.0018(12) N3 0.0137(14) 0.0149(15) 0.0099(14) 0.0000(11) -0.0002(11) 0.0040(12) N4 0.0152(15) 0.0138(15) 0.0124(14) -0.0012(12) 0.0006(12) 0.0021(12) C1 0.0147(18) 0.0204(19) 0.0130(17) 0.0043(14) 0.0025(14) 0.0082(15) C2 0.0201(19) 0.0152(18) 0.0155(18) 0.0017(14) 0.0025(15) 0.0079(15) C3 0.0166(18) 0.0176(18) 0.0126(17) 0.0024(14) 0.0019(14) 0.0038(15) C4 0.021(2) 0.0186(19) 0.0135(18) 0.0006(14) 0.0021(15) 0.0068(16) C5 0.023(2) 0.0158(19) 0.0154(18) 0.0005(15) 0.0060(15) 0.0013(16) C6 0.0157(19) 0.0187(19) 0.0155(18) 0.0011(15) 0.0024(15) 0.0002(15) C7 0.0134(18) 0.0148(18) 0.0115(17) -0.0012(13) -0.0025(14) 0.0019(14) C8 0.0153(18) 0.0199(19) 0.0117(17) 0.0015(14) -0.0012(14) 0.0073(15) C9 0.0232(19) 0.0193(19) 0.0160(18) 0.0025(15) -0.0012(15) 0.0082(16) C10 0.037(2) 0.031(2) 0.0112(18) -0.0009(17) 0.0002(17) 0.018(2) C11 0.029(2) 0.047(3) 0.0149(19) 0.0104(18) 0.0078(17) 0.024(2) C12 0.017(2) 0.040(3) 0.020(2) 0.0129(18) 0.0024(16) 0.0080(18) C13 0.0168(19) 0.026(2) 0.0159(19) 0.0044(16) -0.0027(15) 0.0061(16) C14 0.036(3) 0.021(2) 0.020(2) -0.0063(17) -0.0098(19) 0.0018(19) C15 0.031(2) 0.018(2) 0.025(2) -0.0023(16) -0.0054(17) 0.0026(17) C16 0.029(2) 0.028(2) 0.040(3) 0.007(2) -0.005(2) 0.0019(19) _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 Co1 N1 2.037(3) . ? Co1 N2 2.124(3) . ? Co1 Cl1 2.2680(9) . ? Co1 Cl2 2.3303(9) . ? Co1 Cl2 2.6343(9) 2 ? Cl2 Co1 2.6343(9) 2 ? N1 C3 1.344(4) . ? N1 N3 1.372(3) . ? N2 C4 1.330(4) . ? N2 N4 1.365(3) . ? O1 C9 1.371(4) . ? O1 C14 1.436(4) . ? N3 C1 1.343(4) . ? N3 C7 1.453(4) . ? N4 C6 1.339(4) . ? N4 C7 1.459(4) . ? C1 C2 1.365(4) . ? C2 C3 1.376(4) . ? C4 C5 1.396(5) . ? C5 C6 1.363(5) . ? C7 C8 1.519(4) . ? C8 C13 1.380(4) . ? C8 C9 1.411(4) . ? C9 C10 1.380(5) . ? C10 C11 1.389(5) . ? C11 C12 1.371(5) . ? C12 C13 1.394(5) . ? C14 C15 1.469(5) . ? C15 C16 1.172(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 N1 Co1 N2 87.65(10) . . ? N1 Co1 Cl1 138.93(8) . . ? N2 Co1 Cl1 97.27(7) . . ? N1 Co1 Cl2 106.31(8) . . ? N2 Co1 Cl2 94.88(7) . . ? Cl1 Co1 Cl2 113.78(4) . . ? N1 Co1 Cl2 84.08(8) . 2 ? N2 Co1 Cl2 171.42(7) . 2 ? Cl1 Co1 Cl2 90.50(3) . 2 ? Cl2 Co1 Cl2 85.25(3) . 2 ? Co1 Cl2 Co1 94.75(3) . 2 ? C3 N1 N3 103.5(3) . . ? C3 N1 Co1 130.2(2) . . ? N3 N1 Co1 124.3(2) . . ? C4 N2 N4 104.4(3) . . ? C4 N2 Co1 129.8(2) . . ? N4 N2 Co1 121.9(2) . . ? C9 O1 C14 118.1(3) . . ? C1 N3 N1 111.6(3) . . ? C1 N3 C7 126.8(3) . . ? N1 N3 C7 121.5(3) . . ? C6 N4 N2 111.5(3) . . ? C6 N4 C7 128.3(3) . . ? N2 N4 C7 120.2(3) . . ? N3 C1 C2 107.4(3) . . ? C1 C2 C3 105.5(3) . . ? N1 C3 C2 112.1(3) . . ? N2 C4 C5 111.5(3) . . ? C6 C5 C4 104.9(3) . . ? N4 C6 C5 107.7(3) . . ? N3 C7 N4 108.8(2) . . ? N3 C7 C8 113.7(3) . . ? N4 C7 C8 111.0(3) . . ? C13 C8 C9 118.7(3) . . ? C13 C8 C7 123.6(3) . . ? C9 C8 C7 117.7(3) . . ? O1 C9 C10 125.1(3) . . ? O1 C9 C8 114.8(3) . . ? C10 C9 C8 120.1(3) . . ? C9 C10 C11 119.7(3) . . ? C12 C11 C10 120.7(4) . . ? C11 C12 C13 119.5(4) . . ? C8 C13 C12 120.9(3) . . ? O1 C14 C15 112.1(3) . . ? C16 C15 C14 179.7(5) . . ? _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.939 _refine_diff_density_max 0.674 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.095 # Attachment 'elena6pa.cif' data_elena6pa _database_code_depnum_ccdc_archive 'CCDC 620815' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 N4 O' _chemical_formula_weight 278.31 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.2557(3) _cell_length_b 7.5895(3) _cell_length_c 9.8876(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.411(3) _cell_angle_gamma 90.00 _cell_volume 691.47(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type 'multi-scan correction' _exptl_absorpt_correction_T_min 0.929953 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; (Sheldrick, M. SADABS empirical absorption program, University of Gottingen, 1996) ; _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 'Oxford Diffraction Xcalibur2' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6678 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.94 _diffrn_reflns_theta_max 32.15 _reflns_number_total 3855 _reflns_number_gt 3494 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraciton, 2005)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraciton, 2005)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraciton, 2005)' _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^)+(0.0545P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(10) _refine_ls_number_reflns 3855 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0419 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0910 _refine_ls_wR_factor_gt 0.0891 _refine_ls_goodness_of_fit_ref 1.148 _refine_ls_restrained_S_all 1.148 _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 N1 N 0.22779(11) 0.70833(14) 0.70147(9) 0.01597(19) Uani 1 1 d . . . N2 N 0.21750(11) 0.57984(15) 0.79531(9) 0.0199(2) Uani 1 1 d . . . C13 C 0.07892(12) 1.08909(17) 0.88051(11) 0.0160(2) Uani 1 1 d . . . C14 C -0.16987(13) 1.17752(18) 0.86737(12) 0.0195(2) Uani 1 1 d . . . H14A H -0.1510 1.3033 0.8688 0.023 Uiso 1 1 calc R . . H14B H -0.1764 1.1381 0.9599 0.023 Uiso 1 1 calc R . . N3 N 0.14100(11) 0.96264(14) 0.58311(9) 0.01611(19) Uani 1 1 d . . . N4 N 0.25666(11) 1.06564(15) 0.56214(10) 0.0199(2) Uani 1 1 d . . . C9 C 0.32060(13) 0.96901(17) 0.90087(11) 0.0184(2) Uani 1 1 d . . . H9 H 0.3891 0.8925 0.8706 0.022 Uiso 1 1 calc R . . C4 C 0.30728(14) 0.45509(18) 0.76020(12) 0.0209(2) Uani 1 1 d . . . H4 H 0.3238 0.3497 0.8071 0.025 Uiso 1 1 calc R . . C1 C 0.13793(13) 0.86549(16) 0.70902(11) 0.0155(2) Uani 1 1 d . . . H1 H 0.0378 0.8266 0.7154 0.019 Uiso 1 1 calc R . . C10 C 0.35716(14) 1.07489(18) 1.01468(11) 0.0208(2) Uani 1 1 d . . . H10 H 0.4500 1.0699 1.0596 0.025 Uiso 1 1 calc R . . C11 C 0.25427(14) 1.18702(18) 1.05987(11) 0.0211(2) Uani 1 1 d . . . H11 H 0.2790 1.2584 1.1349 0.025 Uiso 1 1 calc R . . C15 C -0.30478(14) 1.13982(17) 0.78440(12) 0.0207(2) Uani 1 1 d . . . C6 C 0.10972(15) 1.03091(18) 0.36704(12) 0.0220(3) Uani 1 1 d . . . H6 H 0.0733 1.0411 0.2764 0.026 Uiso 1 1 calc R . . C7 C 0.23656(14) 1.10787(19) 0.43083(11) 0.0226(3) Uani 1 1 d . . . H7 H 0.2988 1.1795 0.3868 0.027 Uiso 1 1 calc R . . C8 C 0.18252(12) 0.97736(16) 0.83271(10) 0.0154(2) Uani 1 1 d . . . C12 C 0.11451(14) 1.19483(18) 0.99498(11) 0.0193(2) Uani 1 1 d . . . H12 H 0.0456 1.2692 1.0271 0.023 Uiso 1 1 calc R . . C3 C 0.37404(16) 0.50139(18) 0.64406(14) 0.0274(3) Uani 1 1 d . . . H3 H 0.4406 0.4358 0.6003 0.033 Uiso 1 1 calc R . . C2 C 0.31961(15) 0.66481(17) 0.60910(13) 0.0247(3) Uani 1 1 d . . . H2 H 0.3419 0.7327 0.5356 0.030 Uiso 1 1 calc R . . C5 C 0.05145(14) 0.93776(17) 0.46728(12) 0.0196(2) Uani 1 1 d . . . H5 H -0.0329 0.8705 0.4581 0.024 Uiso 1 1 calc R . . C16 C -0.41839(14) 1.1112(2) 0.72088(12) 0.0248(3) Uani 1 1 d . . . H16 H -0.5070 1.0888 0.6714 0.030 Uiso 1 1 calc R . . O1 O -0.05499(9) 1.08545(13) 0.80862(8) 0.01890(18) 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 N1 0.0172(4) 0.0162(5) 0.0147(4) 0.0003(3) 0.0027(3) 0.0011(4) N2 0.0232(5) 0.0195(5) 0.0170(4) 0.0036(4) 0.0027(3) 0.0014(4) C13 0.0163(5) 0.0177(5) 0.0140(4) 0.0007(4) 0.0015(4) 0.0000(4) C14 0.0181(5) 0.0225(6) 0.0184(5) 0.0001(4) 0.0045(4) 0.0039(5) N3 0.0170(5) 0.0176(5) 0.0134(4) -0.0001(4) -0.0002(3) 0.0007(4) N4 0.0184(5) 0.0214(5) 0.0199(4) 0.0031(4) 0.0013(3) -0.0018(4) C9 0.0163(5) 0.0201(6) 0.0187(5) 0.0020(4) 0.0014(4) -0.0002(5) C4 0.0223(6) 0.0181(6) 0.0219(5) 0.0012(4) 0.0003(4) 0.0003(5) C1 0.0162(5) 0.0158(5) 0.0146(5) -0.0001(4) 0.0017(4) 0.0018(4) C10 0.0192(5) 0.0237(6) 0.0185(5) 0.0030(5) -0.0038(4) -0.0029(5) C11 0.0269(6) 0.0218(6) 0.0144(5) -0.0015(4) 0.0001(4) -0.0045(5) C15 0.0207(6) 0.0222(6) 0.0201(5) 0.0032(4) 0.0065(4) 0.0042(5) C6 0.0246(6) 0.0247(6) 0.0162(5) -0.0005(4) -0.0001(4) 0.0064(5) C7 0.0248(6) 0.0240(6) 0.0194(5) 0.0053(5) 0.0040(4) 0.0024(5) C8 0.0165(5) 0.0163(6) 0.0135(4) 0.0003(4) 0.0015(4) -0.0013(4) C12 0.0232(6) 0.0200(6) 0.0149(5) -0.0019(4) 0.0032(4) 0.0000(5) C3 0.0321(7) 0.0221(7) 0.0301(6) 0.0009(5) 0.0131(5) 0.0077(6) C2 0.0296(7) 0.0225(7) 0.0240(6) 0.0029(5) 0.0130(5) 0.0039(5) C5 0.0195(5) 0.0215(6) 0.0170(5) -0.0019(4) -0.0026(4) 0.0021(5) C16 0.0205(6) 0.0300(7) 0.0244(5) 0.0047(5) 0.0041(4) 0.0025(5) O1 0.0147(4) 0.0248(5) 0.0172(3) -0.0042(3) 0.0015(3) 0.0038(4) _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 1.3461(16) . ? N1 N2 1.3556(14) . ? N1 C1 1.4600(16) . ? N2 C4 1.3273(16) . ? C13 O1 1.3697(13) . ? C13 C8 1.3955(16) . ? C13 C12 1.4011(16) . ? C14 O1 1.4398(14) . ? C14 C15 1.4564(18) . ? N3 N4 1.3572(14) . ? N3 C5 1.3621(14) . ? N3 C1 1.4494(14) . ? N4 C7 1.3332(15) . ? C9 C8 1.3889(15) . ? C9 C10 1.3982(17) . ? C4 C3 1.3992(18) . ? C1 C8 1.5138(15) . ? C10 C11 1.3825(19) . ? C11 C12 1.3900(17) . ? C15 C16 1.1928(18) . ? C6 C5 1.3690(18) . ? C6 C7 1.4062(19) . ? C3 C2 1.3706(18) . ? 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 N2 112.18(10) . . ? C2 N1 C1 129.37(10) . . ? N2 N1 C1 118.40(9) . . ? C4 N2 N1 104.36(9) . . ? O1 C13 C8 115.40(9) . . ? O1 C13 C12 124.27(11) . . ? C8 C13 C12 120.33(10) . . ? O1 C14 C15 107.70(9) . . ? N4 N3 C5 112.19(10) . . ? N4 N3 C1 120.26(9) . . ? C5 N3 C1 126.30(11) . . ? C7 N4 N3 104.33(10) . . ? C8 C9 C10 120.41(11) . . ? N2 C4 C3 111.80(11) . . ? N3 C1 N1 108.32(9) . . ? N3 C1 C8 112.50(10) . . ? N1 C1 C8 112.72(9) . . ? C11 C10 C9 119.48(11) . . ? C10 C11 C12 121.10(11) . . ? C16 C15 C14 177.25(13) . . ? C5 C6 C7 105.01(10) . . ? N4 C7 C6 111.77(12) . . ? C9 C8 C13 119.58(10) . . ? C9 C8 C1 122.32(11) . . ? C13 C8 C1 118.08(10) . . ? C11 C12 C13 119.09(11) . . ? C2 C3 C4 104.72(12) . . ? N1 C2 C3 106.94(11) . . ? N3 C5 C6 106.68(11) . . ? C13 O1 C14 116.58(9) . . ? _diffrn_measured_fraction_theta_max 0.908 _diffrn_reflns_theta_full 32.15 _diffrn_measured_fraction_theta_full 0.908 _refine_diff_density_max 0.223 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.039 # Attachment 'fm02m.cif' data_fm02m _database_code_depnum_ccdc_archive 'CCDC 620816' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 Cl2 N4 O Zn' _chemical_formula_weight 414.58 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1822(4) _cell_length_b 9.1228(5) _cell_length_c 11.7847(6) _cell_angle_alpha 96.5040(10) _cell_angle_beta 95.6410(10) _cell_angle_gamma 103.3830(10) _cell_volume 843.18(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5669 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 28.83 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.633 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 1.784 _exptl_absorpt_correction_type 'multi-scan correction' _exptl_absorpt_correction_T_min 0.852286 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; (Sheldrick, M. SADABS empirical absorption program, University of Gottingen, 1996) ; _diffrn_ambient_temperature 373(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area Detector' _diffrn_measurement_method 'Phi and Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10612 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 28.83 _reflns_number_total 4038 _reflns_number_gt 3727 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BrUKER SMART' _computing_cell_refinement 'BrUKER SMART' _computing_data_reduction 'BRUKER SHELXTL' _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^)+(0.0357P)^2^+0.2713P] 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 4038 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0276 _refine_ls_R_factor_gt 0.0251 _refine_ls_wR_factor_ref 0.0650 _refine_ls_wR_factor_gt 0.0638 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.68083(2) 0.65385(2) 0.643955(15) 0.01629(6) Uani 1 1 d . . . Cl2 Cl 0.60912(5) 0.69137(5) 0.46264(3) 0.02030(9) Uani 1 1 d . . . Cl1 Cl 0.49253(5) 0.66646(5) 0.76470(3) 0.02053(9) Uani 1 1 d . . . N1 N 0.90231(16) 0.82674(15) 0.69417(11) 0.0160(3) Uani 1 1 d . . . N3 N 0.82404(16) 0.49655(15) 0.63840(11) 0.0156(3) Uani 1 1 d . . . N4 N 0.98463(15) 0.52625(14) 0.69494(11) 0.0141(2) Uani 1 1 d . . . N2 N 1.05094(16) 0.79533(15) 0.73123(11) 0.0152(3) Uani 1 1 d . . . O1 O 1.17562(16) 0.87125(14) 0.96720(10) 0.0245(3) Uani 1 1 d . . . C4 C 0.8115(2) 0.37543(18) 0.55948(13) 0.0168(3) Uani 1 1 d . . . C7 C 1.05194(19) 0.65714(17) 0.78326(13) 0.0151(3) Uani 1 1 d . . . C8 C 0.9625(2) 0.65283(18) 0.88979(13) 0.0168(3) Uani 1 1 d . . . C5 C 0.9617(2) 0.32775(18) 0.56545(14) 0.0171(3) Uani 1 1 d . . . C1 C 0.9466(2) 0.95782(18) 0.65133(14) 0.0183(3) Uani 1 1 d . . . C6 C 1.0695(2) 0.42742(18) 0.65167(13) 0.0162(3) Uani 1 1 d . . . C9 C 0.8232(2) 0.5387(2) 0.90114(15) 0.0210(3) Uani 1 1 d . . . C13 C 1.0297(2) 0.76939(19) 0.98280(14) 0.0206(3) Uani 1 1 d . . . C2 C 1.1217(2) 1.01002(19) 0.66154(14) 0.0206(3) Uani 1 1 d . . . C10 C 0.7428(2) 0.5441(2) 0.99972(15) 0.0265(4) Uani 1 1 d . . . C3 C 1.1846(2) 0.90340(18) 0.71283(14) 0.0180(3) Uani 1 1 d . . . C12 C 0.9485(2) 0.7766(2) 1.08028(15) 0.0265(4) Uani 1 1 d . . . C14 C 1.2649(3) 0.9806(2) 1.06359(16) 0.0276(4) Uani 1 1 d . . . C15 C 1.3403(2) 0.9091(2) 1.15429(16) 0.0275(4) Uani 1 1 d . . . C11 C 0.8030(2) 0.6652(2) 1.08659(15) 0.0294(4) Uani 1 1 d . . . C16 C 1.4011(3) 0.8531(2) 1.22764(19) 0.0342(4) Uani 1 1 d . . . H11 H 0.744(3) 0.671(2) 1.1509(19) 0.028(5) Uiso 1 1 d . . . H10 H 0.648(3) 0.468(3) 1.0075(19) 0.031(6) Uiso 1 1 d . . . H14 H 1.356(3) 1.049(2) 1.0297(19) 0.027(5) Uiso 1 1 d . . . H6 H 1.178(2) 0.435(2) 0.6793(16) 0.017(4) Uiso 1 1 d . . . H7 H 1.165(2) 0.6601(19) 0.8025(15) 0.008(4) Uiso 1 1 d . . . H1 H 0.868(3) 0.995(2) 0.6177(18) 0.022(5) Uiso 1 1 d . . . H5 H 0.984(2) 0.248(2) 0.5213(17) 0.017(5) Uiso 1 1 d . . . H4 H 0.712(3) 0.338(2) 0.5110(17) 0.019(5) Uiso 1 1 d . . . H9 H 0.784(2) 0.461(2) 0.8442(18) 0.021(5) Uiso 1 1 d . . . H14A H 1.187(3) 1.034(2) 1.0989(19) 0.030(6) Uiso 1 1 d . . . H3 H 1.288(3) 0.897(2) 0.7319(17) 0.020(5) Uiso 1 1 d . . . H2 H 1.181(3) 1.095(2) 0.6405(17) 0.022(5) Uiso 1 1 d . . . H12 H 0.996(3) 0.856(2) 1.1395(19) 0.028(5) Uiso 1 1 d . . . H16 H 1.448(3) 0.808(3) 1.280(2) 0.049(7) 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 0.01362(10) 0.02099(10) 0.01630(10) 0.00477(7) 0.00315(7) 0.00680(7) Cl2 0.01593(18) 0.0275(2) 0.01910(19) 0.00871(15) 0.00206(14) 0.00595(15) Cl1 0.01464(18) 0.0262(2) 0.02096(19) 0.00088(15) 0.00514(14) 0.00542(14) N1 0.0155(6) 0.0185(6) 0.0156(6) 0.0031(5) 0.0024(5) 0.0066(5) N3 0.0132(6) 0.0192(6) 0.0143(6) 0.0034(5) 0.0010(5) 0.0036(5) N4 0.0124(6) 0.0169(6) 0.0133(6) 0.0030(5) 0.0011(5) 0.0040(5) N2 0.0140(6) 0.0177(6) 0.0141(6) 0.0014(5) 0.0023(5) 0.0041(5) O1 0.0286(6) 0.0248(6) 0.0166(6) -0.0015(5) -0.0008(5) 0.0035(5) C4 0.0157(7) 0.0184(7) 0.0152(7) 0.0027(6) 0.0015(6) 0.0019(6) C7 0.0132(7) 0.0178(7) 0.0138(7) 0.0012(6) 0.0001(5) 0.0041(6) C8 0.0175(7) 0.0231(8) 0.0126(7) 0.0051(6) 0.0025(6) 0.0094(6) C5 0.0200(8) 0.0161(7) 0.0166(7) 0.0032(6) 0.0050(6) 0.0054(6) C1 0.0241(8) 0.0172(7) 0.0150(7) 0.0023(6) 0.0038(6) 0.0075(6) C6 0.0164(7) 0.0185(7) 0.0158(7) 0.0045(6) 0.0038(6) 0.0071(6) C9 0.0188(8) 0.0286(9) 0.0178(8) 0.0082(7) 0.0012(6) 0.0081(7) C13 0.0228(8) 0.0249(8) 0.0167(8) 0.0037(6) 0.0004(6) 0.0115(7) C2 0.0243(8) 0.0175(8) 0.0182(8) 0.0006(6) 0.0054(6) 0.0013(6) C10 0.0189(8) 0.0428(11) 0.0232(9) 0.0158(8) 0.0056(7) 0.0119(8) C3 0.0166(7) 0.0203(7) 0.0150(7) -0.0008(6) 0.0028(6) 0.0013(6) C12 0.0340(10) 0.0360(10) 0.0146(8) 0.0022(7) 0.0027(7) 0.0198(8) C14 0.0381(10) 0.0221(8) 0.0195(8) -0.0024(7) -0.0070(7) 0.0081(8) C15 0.0289(9) 0.0241(8) 0.0259(9) 0.0002(7) -0.0024(7) 0.0033(7) C11 0.0290(9) 0.0527(12) 0.0172(8) 0.0136(8) 0.0093(7) 0.0243(9) C16 0.0298(10) 0.0301(10) 0.0383(11) 0.0113(9) -0.0080(8) 0.0006(8) _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 2.0515(13) . ? Zn1 N1 2.0920(13) . ? Zn1 Cl1 2.2108(4) . ? Zn1 Cl2 2.2448(4) . ? N1 C1 1.337(2) . ? N1 N2 1.3554(18) . ? N3 C4 1.339(2) . ? N3 N4 1.3660(17) . ? N4 C6 1.345(2) . ? N4 C7 1.4538(19) . ? N2 C3 1.346(2) . ? N2 C7 1.464(2) . ? O1 C13 1.375(2) . ? O1 C14 1.436(2) . ? C4 C5 1.393(2) . ? C7 C8 1.514(2) . ? C8 C9 1.383(2) . ? C8 C13 1.408(2) . ? C5 C6 1.371(2) . ? C1 C2 1.390(2) . ? C9 C10 1.392(2) . ? C13 C12 1.385(2) . ? C2 C3 1.371(2) . ? C10 C11 1.379(3) . ? C12 C11 1.390(3) . ? C14 C15 1.471(3) . ? C15 C16 1.178(3) . ? 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 N1 89.37(5) . . ? N3 Zn1 Cl1 124.18(4) . . ? N1 Zn1 Cl1 111.30(4) . . ? N3 Zn1 Cl2 108.08(4) . . ? N1 Zn1 Cl2 101.59(4) . . ? Cl1 Zn1 Cl2 116.679(16) . . ? C1 N1 N2 104.90(13) . . ? C1 N1 Zn1 127.13(11) . . ? N2 N1 Zn1 121.45(10) . . ? C4 N3 N4 104.97(12) . . ? C4 N3 Zn1 129.29(11) . . ? N4 N3 Zn1 122.65(10) . . ? C6 N4 N3 111.14(12) . . ? C6 N4 C7 126.74(13) . . ? N3 N4 C7 121.94(12) . . ? C3 N2 N1 111.58(13) . . ? C3 N2 C7 128.06(13) . . ? N1 N2 C7 120.36(12) . . ? C13 O1 C14 118.38(14) . . ? N3 C4 C5 111.03(14) . . ? N4 C7 N2 108.41(12) . . ? N4 C7 C8 114.29(13) . . ? N2 C7 C8 111.84(12) . . ? C9 C8 C13 119.07(15) . . ? C9 C8 C7 123.48(14) . . ? C13 C8 C7 117.41(14) . . ? C6 C5 C4 105.30(14) . . ? N1 C1 C2 111.09(15) . . ? N4 C6 C5 107.55(14) . . ? C8 C9 C10 120.71(17) . . ? O1 C13 C12 124.72(16) . . ? O1 C13 C8 115.04(14) . . ? C12 C13 C8 120.23(16) . . ? C3 C2 C1 105.28(15) . . ? C11 C10 C9 119.36(18) . . ? N2 C3 C2 107.15(15) . . ? C13 C12 C11 119.32(17) . . ? O1 C14 C15 112.26(15) . . ? C16 C15 C14 179.3(2) . . ? C10 C11 C12 121.02(17) . . ? _diffrn_measured_fraction_theta_max 0.913 _diffrn_reflns_theta_full 28.83 _diffrn_measured_fraction_theta_full 0.913 _refine_diff_density_max 0.459 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.066