# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Mikata, Y.' 'Yamashita, Azusa' 'Kawata, Keiko' 'Konno, Hideo' 'Itami, Saori' 'Yasuda, Keiko' 'Tamotsu, Satoshi' _publ_contact_author_name 'Mikata, Y.' _publ_contact_author_email mikata@cc.nara-wu.ac.jp _publ_section_title ; Methoxyquinoline-diethylenetriamine conjugate as a fluorescent zinc sensor ; # Attachment '- mikata-CIF.CIF' data_6-MeOBQDIEN-Zn _database_code_depnum_ccdc_archive 'CCDC 783520' #TrackingRef '- mikata-CIF.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H31 Cl2 N5 O10 Zn' _chemical_formula_weight 709.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Zn Zn 0.2839 1.4301 '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' C C 0.0033 0.0016 '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' N N 0.0061 0.0033 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 26.5223(8) _cell_length_b 10.5201(3) _cell_length_c 20.1433(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5620.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.678 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2928 _exptl_absorpt_coefficient_mu 1.133 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6013 _exptl_absorpt_correction_T_max 0.7275 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 40647 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6436 _reflns_number_gt 6194 _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^)+(0.0448P)^2^+12.3713P] 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 6436 _refine_ls_number_parameters 530 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1079 _refine_ls_wR_factor_gt 0.1069 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.362882(10) 0.93780(2) 0.146573(13) 0.01798(9) Uani 1 1 d . . . Cl1 Cl 0.27172(2) 0.43410(7) 0.05021(3) 0.03018(15) Uani 1 1 d . . . C15 C 0.36834(11) 1.2178(2) 0.15109(13) 0.0257(5) Uani 1 1 d . . . O1 O 0.46951(7) 0.74437(17) 0.43417(8) 0.0262(4) Uani 1 1 d . . . C2 C 0.41925(9) 0.5666(2) 0.15361(12) 0.0190(4) Uani 1 1 d . . . O2 O 0.30588(7) 0.39659(17) 0.32310(9) 0.0273(4) Uani 1 1 d . . . N2 N 0.35666(8) 0.83307(19) 0.05850(10) 0.0192(4) Uani 1 1 d . . . C25 C 0.31170(8) 0.7467(2) 0.32759(11) 0.0187(4) Uani 1 1 d . . . C13 C 0.42260(11) 0.9878(3) 0.02720(14) 0.0295(5) Uani 1 1 d . . . C7 C 0.43726(9) 0.8822(2) 0.27612(11) 0.0187(4) Uani 1 1 d . . . N5 N 0.31777(7) 0.89241(18) 0.23369(9) 0.0167(4) Uani 1 1 d . . . N1 N 0.41194(7) 0.79081(18) 0.17215(9) 0.0160(4) Uani 1 1 d . . . N4 N 0.33372(8) 1.1171(2) 0.17593(10) 0.0225(4) Uani 1 1 d . . . O3 O 0.32448(8) 0.4313(2) 0.03658(12) 0.0397(5) Uani 1 1 d . . . N3 N 0.41288(8) 1.0555(2) 0.09021(11) 0.0244(4) Uani 1 1 d . . . C6 C 0.45119(9) 0.8675(2) 0.34107(12) 0.0201(4) Uani 1 1 d . . . C3 C 0.43309(9) 0.5468(2) 0.21836(12) 0.0192(4) Uani 1 1 d . . . C5 C 0.45701(9) 0.7444(2) 0.36843(11) 0.0203(4) Uani 1 1 d . . . C20 C 0.31019(9) 0.6202(2) 0.35132(11) 0.0207(5) Uani 1 1 d . . . C17 C 0.31848(8) 0.9890(2) 0.27568(11) 0.0185(4) Uani 1 1 d . . . C22 C 0.30265(9) 0.5472(2) 0.23767(12) 0.0200(4) Uani 1 1 d . . . C9 C 0.43778(8) 0.6515(2) 0.26212(11) 0.0171(4) Uani 1 1 d . . . C8 C 0.42927(8) 0.7741(2) 0.23582(11) 0.0157(4) Uani 1 1 d . . . C23 C 0.30512(8) 0.6686(2) 0.21407(11) 0.0188(4) Uani 1 1 d . . . C4 C 0.45083(9) 0.6376(2) 0.33018(12) 0.0192(4) Uani 1 1 d . . . C10 C 0.47192(12) 0.6231(3) 0.46588(13) 0.0289(5) Uani 1 1 d . . . C26 C 0.31247(13) 0.3666(3) 0.39191(15) 0.0348(6) Uani 1 1 d . . . C24 C 0.31140(8) 0.7713(2) 0.25852(11) 0.0170(4) Uani 1 1 d . . . C1 C 0.40691(8) 0.6909(2) 0.13282(11) 0.0171(4) Uani 1 1 d . . . C16 C 0.32593(9) 1.1204(2) 0.24778(12) 0.0212(4) Uani 1 1 d . . . C21 C 0.30670(9) 0.5221(2) 0.30655(12) 0.0208(4) Uani 1 1 d . . . C19 C 0.31301(9) 0.8528(2) 0.37102(12) 0.0233(5) Uani 1 1 d . . . O4 O 0.26091(10) 0.3553(3) 0.10735(11) 0.0526(7) Uani 1 1 d . . . O5 O 0.24489(9) 0.3864(3) -0.00630(10) 0.0511(7) Uani 1 1 d . . . C18 C 0.31456(10) 0.9725(2) 0.34538(12) 0.0232(5) Uani 1 1 d . . . C12 C 0.37530(11) 0.9187(3) 0.00465(12) 0.0258(5) Uani 1 1 d . . . C11 C 0.38619(10) 0.7134(2) 0.06390(12) 0.0218(5) Uani 1 1 d . . . O6 O 0.25648(14) 0.5616(3) 0.06349(16) 0.0745(10) Uani 1 1 d . . . C14 C 0.38687(12) 1.1789(2) 0.08302(14) 0.0293(6) Uani 1 1 d . . . Cl2 Cl 0.53346(3) 0.24748(7) 0.13532(4) 0.03572(17) Uani 1 1 d . . . O7 O 0.52044(10) 0.1519(2) 0.08889(13) 0.0520(6) Uani 1 1 d . . . O8 O 0.56763(14) 0.2127(4) 0.18272(18) 0.0935(12) Uani 1 1 d . . . O9 O 0.49355(11) 0.3258(3) 0.15261(15) 0.0677(9) Uani 1 1 d . . . O10 O 0.56357(13) 0.3375(3) 0.09175(17) 0.0474(8) Uani 0.73 1 d P . . O11 O 0.4980(3) 0.1434(7) 0.1858(4) 0.0400(18) Uani 0.27 1 d P . . H28 H 0.3023(11) 0.685(3) 0.1680(16) 0.026(7) Uiso 1 1 d . . . H6 H 0.4389(12) 0.581(3) 0.4646(15) 0.023(7) Uiso 1 1 d . . . H27 H 0.2979(11) 0.477(3) 0.2091(15) 0.026(7) Uiso 1 1 d . . . H19 H 0.3511(13) 1.295(3) 0.1507(16) 0.035(9) Uiso 1 1 d . . . H2 H 0.4388(10) 0.465(3) 0.2340(14) 0.018(7) Uiso 1 1 d . . . H17 H 0.3585(12) 1.170(3) 0.0542(16) 0.028(8) Uiso 1 1 d . . . H22 H 0.3536(12) 1.153(3) 0.2682(15) 0.027(8) Uiso 1 1 d . . . H23 H 0.2982(12) 1.170(3) 0.2587(16) 0.030(8) Uiso 1 1 d . . . H7 H 0.4969(13) 0.567(3) 0.4434(16) 0.030(8) Uiso 1 1 d . . . H4 H 0.4567(12) 0.933(3) 0.3672(16) 0.025(8) Uiso 1 1 d . . . H26 H 0.3110(12) 0.602(3) 0.3981(16) 0.027(8) Uiso 1 1 d . . . H3 H 0.4553(12) 0.560(3) 0.3473(15) 0.027(8) Uiso 1 1 d . . . H14 H 0.4511(12) 0.924(3) 0.0363(15) 0.027(8) Uiso 1 1 d . . . H1 H 0.4150(11) 0.500(3) 0.1254(15) 0.023(7) Uiso 1 1 d . . . H5 H 0.4323(11) 0.964(3) 0.2583(15) 0.025(7) Uiso 1 1 d . . . H8 H 0.4811(12) 0.640(3) 0.5110(16) 0.030(8) Uiso 1 1 d . . . H12 H 0.3822(11) 0.871(3) -0.0353(15) 0.025(7) Uiso 1 1 d . . . H11 H 0.3262(13) 0.812(3) 0.0509(15) 0.029(8) Uiso 1 1 d . . . H20 H 0.3955(11) 1.220(3) 0.1816(15) 0.021(7) Uiso 1 1 d . . . H13 H 0.3477(12) 0.974(3) -0.0045(16) 0.030(8) Uiso 1 1 d . . . H9 H 0.3654(12) 0.642(3) 0.0516(17) 0.035(9) Uiso 1 1 d . . . H25 H 0.3114(12) 0.834(3) 0.4189(16) 0.030(8) Uiso 1 1 d . . . H10 H 0.4129(12) 0.716(3) 0.0349(16) 0.030(8) Uiso 1 1 d . . . H21 H 0.3028(13) 1.128(3) 0.1534(17) 0.038(9) Uiso 1 1 d . . . H30 H 0.2853(13) 0.403(3) 0.4186(17) 0.033(8) Uiso 1 1 d . . . H24 H 0.3137(12) 1.043(3) 0.3707(17) 0.032(8) Uiso 1 1 d . . . H31 H 0.3115(16) 0.275(4) 0.395(2) 0.060(12) Uiso 1 1 d . . . H29 H 0.3446(13) 0.391(3) 0.4052(16) 0.032(8) Uiso 1 1 d . . . H16 H 0.4416(14) 1.069(3) 0.1089(18) 0.037(9) Uiso 1 1 d . . . H18 H 0.4086(12) 1.240(3) 0.0622(16) 0.031(8) Uiso 1 1 d . . . H15 H 0.4312(13) 1.044(3) -0.0069(18) 0.035(9) 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 0.02434(16) 0.01492(14) 0.01469(14) 0.00061(9) -0.00053(9) 0.00220(9) Cl1 0.0264(3) 0.0407(4) 0.0234(3) -0.0068(2) 0.0005(2) -0.0047(2) C15 0.0348(14) 0.0165(11) 0.0258(12) 0.0024(9) 0.0020(10) 0.0020(10) O1 0.0394(10) 0.0227(9) 0.0164(8) -0.0011(7) -0.0064(7) 0.0062(7) C2 0.0207(11) 0.0152(10) 0.0211(11) -0.0040(8) 0.0007(8) -0.0003(8) O2 0.0387(10) 0.0171(8) 0.0260(9) -0.0004(7) 0.0005(8) 0.0009(7) N2 0.0179(9) 0.0222(10) 0.0174(9) 0.0002(7) -0.0012(7) 0.0005(8) C25 0.0170(10) 0.0210(11) 0.0179(10) -0.0025(8) 0.0013(8) -0.0002(8) C13 0.0352(14) 0.0250(13) 0.0283(13) 0.0003(10) 0.0119(11) -0.0029(11) C7 0.0204(10) 0.0145(10) 0.0213(11) 0.0006(8) -0.0004(8) 0.0008(8) N5 0.0151(8) 0.0174(9) 0.0176(9) -0.0020(7) -0.0001(7) 0.0009(7) N1 0.0168(8) 0.0150(8) 0.0163(8) 0.0003(7) 0.0002(7) 0.0011(7) N4 0.0231(10) 0.0213(10) 0.0232(10) 0.0012(8) -0.0021(8) 0.0004(8) O3 0.0254(10) 0.0453(13) 0.0485(13) 0.0155(10) -0.0021(9) -0.0085(9) N3 0.0226(10) 0.0216(10) 0.0290(11) -0.0002(8) 0.0020(8) -0.0006(8) C6 0.0220(11) 0.0176(11) 0.0206(11) -0.0033(9) -0.0009(9) 0.0004(9) C3 0.0202(11) 0.0139(10) 0.0234(11) 0.0002(8) 0.0006(9) 0.0019(8) C5 0.0209(11) 0.0231(11) 0.0168(10) 0.0002(9) -0.0013(8) 0.0045(9) C20 0.0223(11) 0.0220(11) 0.0179(11) -0.0011(9) 0.0016(8) -0.0007(9) C17 0.0154(10) 0.0194(11) 0.0207(11) -0.0030(8) -0.0010(8) 0.0002(8) C22 0.0198(11) 0.0194(11) 0.0207(11) -0.0062(9) 0.0017(8) -0.0009(8) C9 0.0152(9) 0.0159(10) 0.0201(10) -0.0003(8) 0.0007(8) 0.0023(8) C8 0.0140(9) 0.0165(10) 0.0166(10) 0.0002(8) 0.0003(7) 0.0006(8) C23 0.0170(10) 0.0220(11) 0.0173(10) -0.0039(8) 0.0016(8) -0.0017(8) C4 0.0211(11) 0.0160(10) 0.0206(11) 0.0024(8) -0.0011(8) 0.0027(8) C10 0.0409(15) 0.0266(13) 0.0191(11) 0.0027(10) -0.0026(10) 0.0072(11) C26 0.0503(18) 0.0231(13) 0.0310(14) 0.0051(11) -0.0062(13) 0.0008(12) C24 0.0141(9) 0.0186(10) 0.0184(10) -0.0024(8) 0.0008(8) 0.0005(8) C1 0.0168(10) 0.0169(10) 0.0177(10) -0.0011(8) 0.0018(8) -0.0003(8) C16 0.0214(11) 0.0178(11) 0.0243(11) -0.0033(9) -0.0018(9) 0.0008(9) C21 0.0197(10) 0.0186(11) 0.0241(11) -0.0008(9) 0.0021(8) -0.0003(8) C19 0.0274(12) 0.0238(12) 0.0188(11) -0.0034(9) 0.0004(9) -0.0009(9) O4 0.0549(14) 0.0760(18) 0.0267(10) 0.0015(11) 0.0046(10) -0.0317(13) O5 0.0353(11) 0.094(2) 0.0238(10) -0.0152(12) 0.0010(9) -0.0213(12) C18 0.0276(12) 0.0217(11) 0.0204(11) -0.0077(9) 0.0003(9) -0.0006(10) C12 0.0355(14) 0.0263(12) 0.0157(11) 0.0041(9) 0.0005(10) 0.0043(11) C11 0.0306(12) 0.0176(11) 0.0173(10) -0.0023(8) -0.0003(9) 0.0010(9) O6 0.096(2) 0.0633(19) 0.0638(18) -0.0223(15) -0.0006(17) 0.0354(17) C14 0.0407(15) 0.0184(11) 0.0289(13) 0.0073(10) 0.0076(11) 0.0014(11) Cl2 0.0331(3) 0.0313(3) 0.0428(4) -0.0143(3) -0.0139(3) 0.0139(3) O7 0.0553(15) 0.0435(13) 0.0571(15) -0.0208(12) -0.0063(12) 0.0100(11) O8 0.084(2) 0.119(3) 0.078(2) 0.009(2) -0.0505(19) 0.023(2) O9 0.0547(16) 0.0697(19) 0.079(2) -0.0360(16) -0.0004(14) 0.0297(14) O10 0.0542(19) 0.0365(16) 0.0515(19) -0.0018(14) 0.0123(15) -0.0154(14) O11 0.058(5) 0.029(4) 0.033(4) 0.011(3) 0.013(4) -0.005(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 Zn1 N1 2.0856(18) . ? Zn1 N2 2.095(2) . ? Zn1 N4 2.123(2) . ? Zn1 N3 2.140(2) . ? Zn1 N5 2.1769(19) . ? Cl1 O3 1.426(2) . ? Cl1 O6 1.427(3) . ? Cl1 O5 1.433(2) . ? Cl1 O4 1.447(2) . ? C15 N4 1.488(3) . ? C15 C14 1.513(4) . ? C15 H19 0.93(4) . ? C15 H20 0.95(3) . ? O1 C5 1.365(3) . ? O1 C10 1.428(3) . ? C2 C3 1.371(3) . ? C2 C1 1.411(3) . ? C2 H1 0.91(3) . ? O2 C21 1.362(3) . ? O2 C26 1.432(3) . ? N2 C11 1.486(3) . ? N2 C12 1.494(3) . ? N2 H11 0.85(3) . ? C25 C20 1.414(3) . ? C25 C24 1.415(3) . ? C25 C19 1.419(3) . ? C13 N3 1.478(3) . ? C13 C12 1.519(4) . ? C13 H14 1.03(3) . ? C13 H15 0.94(4) . ? C7 C6 1.368(3) . ? C7 C8 1.413(3) . ? C7 H5 0.94(3) . ? N5 C17 1.322(3) . ? N5 C24 1.379(3) . ? N1 C1 1.323(3) . ? N1 C8 1.374(3) . ? N4 C16 1.462(3) . ? N4 H21 0.94(4) . ? N3 C14 1.478(3) . ? N3 H16 0.86(4) . ? C6 C5 1.416(3) . ? C6 H4 0.88(3) . ? C3 C9 1.416(3) . ? C3 H2 0.92(3) . ? C5 C4 1.372(3) . ? C20 C21 1.374(3) . ? C20 H26 0.96(3) . ? C17 C18 1.419(3) . ? C17 C16 1.506(3) . ? C22 C23 1.364(3) . ? C22 C21 1.416(3) . ? C22 H27 0.95(3) . ? C9 C8 1.413(3) . ? C9 C4 1.421(3) . ? C23 C24 1.413(3) . ? C23 H28 0.95(3) . ? C4 H3 0.90(3) . ? C10 H6 0.98(3) . ? C10 H7 0.99(3) . ? C10 H8 0.96(3) . ? C26 H30 0.98(3) . ? C26 H31 0.97(4) . ? C26 H29 0.93(4) . ? C1 C11 1.512(3) . ? C16 H22 0.91(3) . ? C16 H23 0.93(3) . ? C19 C18 1.361(4) . ? C19 H25 0.98(3) . ? C18 H24 0.90(3) . ? C12 H12 0.96(3) . ? C12 H13 0.95(3) . ? C11 H9 0.97(3) . ? C11 H10 0.92(3) . ? C14 H17 0.96(3) . ? C14 H18 0.96(3) . ? Cl2 O8 1.366(3) . ? Cl2 O9 1.386(2) . ? Cl2 O7 1.416(2) . ? Cl2 O10 1.518(3) . ? Cl2 O11 1.766(7) . ? 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 Zn1 N2 82.44(8) . . ? N1 Zn1 N4 144.82(8) . . ? N2 Zn1 N4 132.42(8) . . ? N1 Zn1 N3 99.98(8) . . ? N2 Zn1 N3 84.47(8) . . ? N4 Zn1 N3 81.92(8) . . ? N1 Zn1 N5 88.92(7) . . ? N2 Zn1 N5 121.60(8) . . ? N4 Zn1 N5 76.71(8) . . ? N3 Zn1 N5 153.52(8) . . ? O3 Cl1 O6 109.48(19) . . ? O3 Cl1 O5 109.08(14) . . ? O6 Cl1 O5 109.74(19) . . ? O3 Cl1 O4 109.60(14) . . ? O6 Cl1 O4 109.49(19) . . ? O5 Cl1 O4 109.43(15) . . ? N4 C15 C14 108.3(2) . . ? N4 C15 H19 109(2) . . ? C14 C15 H19 113(2) . . ? N4 C15 H20 105.7(18) . . ? C14 C15 H20 110.3(18) . . ? H19 C15 H20 111(3) . . ? C5 O1 C10 116.42(19) . . ? C3 C2 C1 119.0(2) . . ? C3 C2 H1 120.8(19) . . ? C1 C2 H1 119.9(19) . . ? C21 O2 C26 116.6(2) . . ? C11 N2 C12 112.92(19) . . ? C11 N2 Zn1 109.99(14) . . ? C12 N2 Zn1 105.76(15) . . ? C11 N2 H11 107(2) . . ? C12 N2 H11 110(2) . . ? Zn1 N2 H11 111(2) . . ? C20 C25 C24 120.3(2) . . ? C20 C25 C19 122.2(2) . . ? C24 C25 C19 117.5(2) . . ? N3 C13 C12 110.1(2) . . ? N3 C13 H14 106.8(18) . . ? C12 C13 H14 110.4(17) . . ? N3 C13 H15 112(2) . . ? C12 C13 H15 107(2) . . ? H14 C13 H15 111(3) . . ? C6 C7 C8 119.9(2) . . ? C6 C7 H5 120.4(19) . . ? C8 C7 H5 119.7(19) . . ? C17 N5 C24 118.67(19) . . ? C17 N5 Zn1 109.83(15) . . ? C24 N5 Zn1 124.20(14) . . ? C1 N1 C8 119.43(19) . . ? C1 N1 Zn1 112.23(15) . . ? C8 N1 Zn1 122.28(14) . . ? C16 N4 C15 113.8(2) . . ? C16 N4 Zn1 110.38(15) . . ? C15 N4 Zn1 108.28(15) . . ? C16 N4 H21 111(2) . . ? C15 N4 H21 107(2) . . ? Zn1 N4 H21 107(2) . . ? C13 N3 C14 114.9(2) . . ? C13 N3 Zn1 106.57(15) . . ? C14 N3 Zn1 105.73(16) . . ? C13 N3 H16 107(2) . . ? C14 N3 H16 108(2) . . ? Zn1 N3 H16 114(2) . . ? C7 C6 C5 120.3(2) . . ? C7 C6 H4 122(2) . . ? C5 C6 H4 118(2) . . ? C2 C3 C9 119.8(2) . . ? C2 C3 H2 120.5(17) . . ? C9 C3 H2 119.6(18) . . ? O1 C5 C4 125.0(2) . . ? O1 C5 C6 113.8(2) . . ? C4 C5 C6 121.1(2) . . ? C21 C20 C25 119.1(2) . . ? C21 C20 H26 119.5(19) . . ? C25 C20 H26 121.4(19) . . ? N5 C17 C18 122.5(2) . . ? N5 C17 C16 118.0(2) . . ? C18 C17 C16 119.5(2) . . ? C23 C22 C21 120.8(2) . . ? C23 C22 H27 121.8(19) . . ? C21 C22 H27 117.3(19) . . ? C8 C9 C3 117.6(2) . . ? C8 C9 C4 119.6(2) . . ? C3 C9 C4 122.8(2) . . ? N1 C8 C7 118.9(2) . . ? N1 C8 C9 121.3(2) . . ? C7 C8 C9 119.7(2) . . ? C22 C23 C24 120.0(2) . . ? C22 C23 H28 120.7(19) . . ? C24 C23 H28 119.3(19) . . ? C5 C4 C9 119.1(2) . . ? C5 C4 H3 121(2) . . ? C9 C4 H3 120(2) . . ? O1 C10 H6 110.4(17) . . ? O1 C10 H7 110.7(18) . . ? H6 C10 H7 109(3) . . ? O1 C10 H8 105.6(19) . . ? H6 C10 H8 110(3) . . ? H7 C10 H8 112(3) . . ? O2 C26 H30 111(2) . . ? O2 C26 H31 106(3) . . ? H30 C26 H31 110(3) . . ? O2 C26 H29 109(2) . . ? H30 C26 H29 114(3) . . ? H31 C26 H29 106(3) . . ? N5 C24 C23 119.4(2) . . ? N5 C24 C25 121.7(2) . . ? C23 C24 C25 118.9(2) . . ? N1 C1 C2 122.3(2) . . ? N1 C1 C11 117.5(2) . . ? C2 C1 C11 120.2(2) . . ? N4 C16 C17 111.49(19) . . ? N4 C16 H22 110(2) . . ? C17 C16 H22 107(2) . . ? N4 C16 H23 111(2) . . ? C17 C16 H23 109(2) . . ? H22 C16 H23 109(3) . . ? O2 C21 C20 124.7(2) . . ? O2 C21 C22 114.8(2) . . ? C20 C21 C22 120.5(2) . . ? C18 C19 C25 119.6(2) . . ? C18 C19 H25 123.9(19) . . ? C25 C19 H25 116.4(19) . . ? C19 C18 C17 119.4(2) . . ? C19 C18 H24 123(2) . . ? C17 C18 H24 118(2) . . ? N2 C12 C13 110.2(2) . . ? N2 C12 H12 111.0(18) . . ? C13 C12 H12 109.9(18) . . ? N2 C12 H13 105(2) . . ? C13 C12 H13 114(2) . . ? H12 C12 H13 107(3) . . ? N2 C11 C1 113.06(18) . . ? N2 C11 H9 110(2) . . ? C1 C11 H9 109(2) . . ? N2 C11 H10 110(2) . . ? C1 C11 H10 108(2) . . ? H9 C11 H10 107(3) . . ? N3 C14 C15 107.5(2) . . ? N3 C14 H17 110(2) . . ? C15 C14 H17 108.8(19) . . ? N3 C14 H18 110.6(19) . . ? C15 C14 H18 114.2(19) . . ? H17 C14 H18 106(3) . . ? O8 Cl2 O9 119.3(2) . . ? O8 Cl2 O7 115.7(2) . . ? O9 Cl2 O7 113.70(17) . . ? O8 Cl2 O10 102.8(2) . . ? O9 Cl2 O10 100.1(2) . . ? O7 Cl2 O10 100.92(18) . . ? O8 Cl2 O11 77.6(4) . . ? O9 Cl2 O11 79.4(3) . . ? O7 Cl2 O11 79.1(3) . . ? O10 Cl2 O11 179.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Zn1 N2 C11 3.69(15) . . . . ? N4 Zn1 N2 C11 178.32(14) . . . . ? N3 Zn1 N2 C11 104.55(16) . . . . ? N5 Zn1 N2 C11 -80.34(17) . . . . ? N1 Zn1 N2 C12 -118.54(16) . . . . ? N4 Zn1 N2 C12 56.09(19) . . . . ? N3 Zn1 N2 C12 -17.68(16) . . . . ? N5 Zn1 N2 C12 157.43(14) . . . . ? N1 Zn1 N5 C17 115.79(15) . . . . ? N2 Zn1 N5 C17 -163.78(14) . . . . ? N4 Zn1 N5 C17 -31.82(15) . . . . ? N3 Zn1 N5 C17 5.2(3) . . . . ? N1 Zn1 N5 C24 -33.73(17) . . . . ? N2 Zn1 N5 C24 46.70(19) . . . . ? N4 Zn1 N5 C24 178.65(18) . . . . ? N3 Zn1 N5 C24 -144.28(19) . . . . ? N2 Zn1 N1 C1 -15.77(15) . . . . ? N4 Zn1 N1 C1 171.12(15) . . . . ? N3 Zn1 N1 C1 -98.76(16) . . . . ? N5 Zn1 N1 C1 106.32(15) . . . . ? N2 Zn1 N1 C8 -168.14(18) . . . . ? N4 Zn1 N1 C8 18.7(2) . . . . ? N3 Zn1 N1 C8 108.87(17) . . . . ? N5 Zn1 N1 C8 -46.05(17) . . . . ? C14 C15 N4 C16 161.3(2) . . . . ? C14 C15 N4 Zn1 38.2(2) . . . . ? N1 Zn1 N4 C16 -38.4(2) . . . . ? N2 Zn1 N4 C16 150.89(15) . . . . ? N3 Zn1 N4 C16 -134.26(17) . . . . ? N5 Zn1 N4 C16 29.99(15) . . . . ? N1 Zn1 N4 C15 86.8(2) . . . . ? N2 Zn1 N4 C15 -83.97(18) . . . . ? N3 Zn1 N4 C15 -9.12(16) . . . . ? N5 Zn1 N4 C15 155.13(17) . . . . ? C12 C13 N3 C14 -80.6(3) . . . . ? C12 C13 N3 Zn1 36.1(2) . . . . ? N1 Zn1 N3 C13 71.27(18) . . . . ? N2 Zn1 N3 C13 -10.03(17) . . . . ? N4 Zn1 N3 C13 -144.31(18) . . . . ? N5 Zn1 N3 C13 179.35(17) . . . . ? N1 Zn1 N3 C14 -166.07(17) . . . . ? N2 Zn1 N3 C14 112.63(18) . . . . ? N4 Zn1 N3 C14 -21.65(17) . . . . ? N5 Zn1 N3 C14 -58.0(3) . . . . ? C8 C7 C6 C5 -0.8(4) . . . . ? C1 C2 C3 C9 -3.8(3) . . . . ? C10 O1 C5 C4 -5.6(4) . . . . ? C10 O1 C5 C6 175.1(2) . . . . ? C7 C6 C5 O1 -178.1(2) . . . . ? C7 C6 C5 C4 2.6(4) . . . . ? C24 C25 C20 C21 -2.2(3) . . . . ? C19 C25 C20 C21 177.1(2) . . . . ? C24 N5 C17 C18 2.0(3) . . . . ? Zn1 N5 C17 C18 -149.40(19) . . . . ? C24 N5 C17 C16 179.46(19) . . . . ? Zn1 N5 C17 C16 28.0(2) . . . . ? C2 C3 C9 C8 -1.9(3) . . . . ? C2 C3 C9 C4 178.5(2) . . . . ? C1 N1 C8 C7 176.4(2) . . . . ? Zn1 N1 C8 C7 -33.1(3) . . . . ? C1 N1 C8 C9 -5.5(3) . . . . ? Zn1 N1 C8 C9 145.01(17) . . . . ? C6 C7 C8 N1 175.5(2) . . . . ? C6 C7 C8 C9 -2.6(3) . . . . ? C3 C9 C8 N1 6.7(3) . . . . ? C4 C9 C8 N1 -173.7(2) . . . . ? C3 C9 C8 C7 -175.2(2) . . . . ? C4 C9 C8 C7 4.4(3) . . . . ? C21 C22 C23 C24 -0.5(3) . . . . ? O1 C5 C4 C9 -180.0(2) . . . . ? C6 C5 C4 C9 -0.7(3) . . . . ? C8 C9 C4 C5 -2.7(3) . . . . ? C3 C9 C4 C5 176.8(2) . . . . ? C17 N5 C24 C23 173.2(2) . . . . ? Zn1 N5 C24 C23 -39.7(3) . . . . ? C17 N5 C24 C25 -7.7(3) . . . . ? Zn1 N5 C24 C25 139.40(18) . . . . ? C22 C23 C24 N5 175.0(2) . . . . ? C22 C23 C24 C25 -4.1(3) . . . . ? C20 C25 C24 N5 -173.6(2) . . . . ? C19 C25 C24 N5 7.0(3) . . . . ? C20 C25 C24 C23 5.5(3) . . . . ? C19 C25 C24 C23 -173.8(2) . . . . ? C8 N1 C1 C2 -0.7(3) . . . . ? Zn1 N1 C1 C2 -153.93(18) . . . . ? C8 N1 C1 C11 178.2(2) . . . . ? Zn1 N1 C1 C11 24.9(2) . . . . ? C3 C2 C1 N1 5.4(3) . . . . ? C3 C2 C1 C11 -173.5(2) . . . . ? C15 N4 C16 C17 -146.8(2) . . . . ? Zn1 N4 C16 C17 -24.8(2) . . . . ? N5 C17 C16 N4 -2.7(3) . . . . ? C18 C17 C16 N4 174.8(2) . . . . ? C26 O2 C21 C20 -4.3(4) . . . . ? C26 O2 C21 C22 176.9(2) . . . . ? C25 C20 C21 O2 178.7(2) . . . . ? C25 C20 C21 C22 -2.5(3) . . . . ? C23 C22 C21 O2 -177.2(2) . . . . ? C23 C22 C21 C20 3.9(4) . . . . ? C20 C25 C19 C18 179.8(2) . . . . ? C24 C25 C19 C18 -0.8(3) . . . . ? C25 C19 C18 C17 -4.5(4) . . . . ? N5 C17 C18 C19 4.1(4) . . . . ? C16 C17 C18 C19 -173.3(2) . . . . ? C11 N2 C12 C13 -77.6(3) . . . . ? Zn1 N2 C12 C13 42.8(2) . . . . ? N3 C13 C12 N2 -54.7(3) . . . . ? C12 N2 C11 C1 125.2(2) . . . . ? Zn1 N2 C11 C1 7.3(2) . . . . ? N1 C1 C11 N2 -22.0(3) . . . . ? C2 C1 C11 N2 156.9(2) . . . . ? C13 N3 C14 C15 165.8(2) . . . . ? Zn1 N3 C14 C15 48.6(2) . . . . ? N4 C15 C14 N3 -59.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.524 _refine_diff_density_min -1.320 _refine_diff_density_rms 0.076