data_global #=== _publ_contact_author_name ; Prof. Claudio N. Verani ; _publ_contact_author_address ; Department of Chemistry Wayne State University Detroit, Michigan 48202 USA ; _publ_contact_author_email 'cnverani@chem.wayne.edu' _publ_requested_journal 'Inorg. Chem.' _publ_section_title ; Comparative Activities of Nickel(II) and Zinc(II) Complexes of Asymmetric [NN'O] Ligands as 26S Proteasome Inhibitors ; loop_ _publ_author_name _publ_author_address 'Michael Frezza' ; Department of Pathology School of Medicine Wayne State University Detroit, Michigan 48201 USA ; 'Sarmad Sahiel Hindo' ; Department of Chemistry Wayne State University Detroit, Michigan 48202 USA ; 'Dajena Tomca' ; Department of Chemistry Wayne State University Detroit, Michigan 48202 USA ; 'Marco Allard' ; Department of Chemistry Wayne State University Detroit, Michigan 48202 USA ; 'Qiuzhi Cindy Cui' ; Department of Pathology School of Medicine Wayne State University Detroit, Michigan 48201 USA ; 'Mary Jane Heeg' ; Department of Chemistry Wayne State University Detroit, Michigan 48202 USA ; 'Di Chen' ; Department of Pathology School of Medicine Wayne State University Detroit, Michigan 48201 USA ; 'Claudio N. Verani' ; Department of Chemistry Wayne State University Detroit, Michigan 48202 USA ; 'Q. Ping Dou' ; Department of Pathology School of Medicine Wayne State University Detroit, Michigan 48201 USA ; #=== data_nsar _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H25 Cl9 I4 N4 Ni O2' _chemical_formula_weight 1346.89 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' 'Ni' 'Ni' 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 '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 'P21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 18.4231(5) _cell_length_b 10.1797(3) _cell_length_c 22.1493(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.8120(10) _cell_angle_gamma 90.00 _cell_volume 4148.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9905 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 28.0 _exptl_crystal_description 'plates' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.156 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2544 _exptl_absorpt_coefficient_mu 4.057 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5813 _exptl_absorpt_correction_T_max 0.7928 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 ? _diffrn_measurement_method 'Bruker APEX2' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 86456 _diffrn_reflns_av_R_equivalents 0.0663 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 28.32 _reflns_number_total 10307 _reflns_number_gt 7578 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker APEX2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-Plus _computing_publication_material SHELXL-97 _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^)+(0.0240P)^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 10307 _refine_ls_number_parameters 442 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0644 _refine_ls_wR_factor_gt 0.0591 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 I1 I -0.124734(15) -0.79697(2) 0.413060(12) 0.02416(7) Uani 1 1 d . . . I2 I -0.249342(14) -0.37420(2) 0.247853(12) 0.02279(7) Uani 1 1 d . . . I3 I 0.125535(15) 0.36196(2) 0.088927(12) 0.02390(7) Uani 1 1 d . . . I4 I 0.245934(14) -0.09930(2) 0.233335(12) 0.02214(7) Uani 1 1 d . . . Ni1 Ni -0.00147(3) -0.23748(4) 0.23982(2) 0.01275(10) Uani 1 1 d . . . N1 N -0.02563(16) -0.2463(3) 0.33129(13) 0.0146(7) Uani 1 1 d . . . C1 C -0.0821(2) -0.1940(3) 0.35889(17) 0.0194(9) Uani 1 1 d . . . H1 H -0.1161 -0.1434 0.3352 0.023 Uiso 1 1 calc R . . C2 C -0.0935(2) -0.2093(4) 0.41921(17) 0.0247(9) Uani 1 1 d . . . H2 H -0.1341 -0.1697 0.4369 0.030 Uiso 1 1 calc R . . C3 C -0.0441(2) -0.2843(4) 0.45368(18) 0.0297(11) Uani 1 1 d . . . H3 H -0.0498 -0.2965 0.4957 0.036 Uiso 1 1 calc R . . C4 C 0.0127(2) -0.3399(4) 0.42618(17) 0.0245(10) Uani 1 1 d . . . H4 H 0.0466 -0.3928 0.4490 0.029 Uiso 1 1 calc R . . C5 C 0.0215(2) -0.3197(3) 0.36476(16) 0.0166(8) Uani 1 1 d . . . C6 C 0.0853(2) -0.3738(3) 0.33285(15) 0.0174(8) Uani 1 1 d . . . H6A H 0.1272 -0.3137 0.3392 0.021 Uiso 1 1 calc R . . H6B H 0.0991 -0.4600 0.3506 0.021 Uiso 1 1 calc R . . N2 N 0.06861(16) -0.3897(3) 0.26734(13) 0.0134(7) Uani 1 1 d . . . C7 C 0.03809(19) -0.5218(3) 0.25102(16) 0.0148(8) Uani 1 1 d . . . H7A H 0.0724 -0.5907 0.2660 0.018 Uiso 1 1 calc R . . H7B H 0.0327 -0.5295 0.2065 0.018 Uiso 1 1 calc R . . C8 C -0.03430(19) -0.5435(3) 0.27748(15) 0.0127(8) Uani 1 1 d . . . C9 C -0.0436(2) -0.6401(3) 0.32056(16) 0.0161(8) Uani 1 1 d . . . H9 H -0.0037 -0.6934 0.3341 0.019 Uiso 1 1 calc R . . C10 C -0.1117(2) -0.6587(3) 0.34395(16) 0.0155(8) Uani 1 1 d . . . C11 C -0.1712(2) -0.5838(3) 0.32412(15) 0.0151(8) Uani 1 1 d . . . H11 H -0.2177 -0.5984 0.3397 0.018 Uiso 1 1 calc R . . C12 C -0.16142(19) -0.4870(3) 0.28104(15) 0.0134(8) Uani 1 1 d . . . C13 C -0.0937(2) -0.4615(3) 0.25689(15) 0.0143(8) Uani 1 1 d . . . O1 O -0.08431(13) -0.3670(2) 0.21780(10) 0.0151(5) Uani 1 1 d . . . N3 N 0.02459(16) -0.2246(3) 0.14925(13) 0.0146(7) Uani 1 1 d . . . C14 C 0.0832(2) -0.2723(3) 0.12317(17) 0.0198(9) Uani 1 1 d . . . H14 H 0.1181 -0.3190 0.1479 0.024 Uiso 1 1 calc R . . C15 C 0.0960(2) -0.2578(4) 0.06280(17) 0.0230(9) Uani 1 1 d . . . H15 H 0.1383 -0.2934 0.0462 0.028 Uiso 1 1 calc R . . C16 C 0.0449(2) -0.1890(4) 0.02688(18) 0.0287(10) Uani 1 1 d . . . H16 H 0.0511 -0.1784 -0.0152 0.034 Uiso 1 1 calc R . . C17 C -0.0153(2) -0.1361(3) 0.05341(17) 0.0244(10) Uani 1 1 d . . . H17 H -0.0505 -0.0874 0.0299 0.029 Uiso 1 1 calc R . . C18 C -0.0235(2) -0.1551(3) 0.11468(16) 0.0171(9) Uani 1 1 d . . . C19 C -0.0879(2) -0.1020(3) 0.14620(16) 0.0191(9) Uani 1 1 d . . . H19A H -0.1018 -0.0159 0.1284 0.023 Uiso 1 1 calc R . . H19B H -0.1295 -0.1626 0.1394 0.023 Uiso 1 1 calc R . . N4 N -0.07248(16) -0.0860(3) 0.21183(13) 0.0146(7) Uani 1 1 d . . . C20 C -0.04314(19) 0.0460(3) 0.22931(16) 0.0158(8) Uani 1 1 d . . . H20A H -0.0405 0.0530 0.2739 0.019 Uiso 1 1 calc R . . H20B H -0.0772 0.1142 0.2134 0.019 Uiso 1 1 calc R . . C21 C 0.0311(2) 0.0725(3) 0.20625(15) 0.0137(8) Uani 1 1 d . . . C22 C 0.0423(2) 0.1771(3) 0.16770(16) 0.0172(8) Uani 1 1 d . . . H22 H 0.0023 0.2305 0.1545 0.021 Uiso 1 1 calc R . . C23 C 0.1103(2) 0.2044(3) 0.14831(16) 0.0171(8) Uani 1 1 d . . . C24 C 0.1698(2) 0.1278(3) 0.16668(15) 0.0163(8) Uani 1 1 d . . . H24 H 0.2169 0.1465 0.1533 0.020 Uiso 1 1 calc R . . C25 C 0.15822(19) 0.0232(3) 0.20510(16) 0.0150(8) Uani 1 1 d . . . C26 C 0.0899(2) -0.0092(3) 0.22630(16) 0.0146(8) Uani 1 1 d . . . O2 O 0.08039(13) -0.1097(2) 0.26236(10) 0.0148(6) Uani 1 1 d . . . H1N2 H 0.1162 -0.3965 0.2562 0.050 Uiso 1 1 d . . . H1N4 H -0.1188 -0.0959 0.2367 0.050 Uiso 1 1 d . . . C27 C 0.3663(2) 0.4970(3) 0.11684(17) 0.0226(9) Uani 1 1 d . . . H27 H 0.3763 0.4520 0.1565 0.027 Uiso 1 1 calc R . . Cl1 Cl 0.32977(6) 0.38142(10) 0.06499(5) 0.0305(3) Uani 1 1 d . . . Cl2 Cl 0.44835(6) 0.56165(11) 0.09254(6) 0.0428(3) Uani 1 1 d . . . Cl3 Cl 0.30368(7) 0.62513(10) 0.12739(6) 0.0469(3) Uani 1 1 d . . . C28 C 0.1455(2) 0.5141(4) -0.10362(16) 0.0230(9) Uani 1 1 d . . . H28 H 0.1495 0.4357 -0.1304 0.028 Uiso 1 1 calc R . . Cl4 Cl 0.21224(6) 0.50204(10) -0.04408(4) 0.0280(2) Uani 1 1 d . . . Cl5 Cl 0.05877(6) 0.51620(12) -0.07523(5) 0.0433(3) Uani 1 1 d . . . Cl6 Cl 0.16049(8) 0.65624(10) -0.14629(5) 0.0455(4) Uani 1 1 d . . . C29 C 0.2756(2) -0.0019(4) -0.01471(17) 0.0246(9) Uani 1 1 d . . . H29 H 0.3180 0.0353 -0.0355 0.029 Uiso 1 1 calc R . . Cl7 Cl 0.23242(6) -0.11876(9) -0.06284(5) 0.0296(3) Uani 1 1 d . . . Cl8 Cl 0.21615(7) 0.12664(10) 0.00071(5) 0.0397(3) Uani 1 1 d . . . Cl9 Cl 0.30796(7) -0.07866(12) 0.05211(5) 0.0481(3) 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 I1 0.02560(16) 0.02037(13) 0.02709(15) 0.00981(11) 0.00707(12) 0.00124(11) I2 0.01343(14) 0.02617(14) 0.02886(15) 0.00684(11) 0.00175(11) 0.00499(11) I3 0.02369(16) 0.01708(13) 0.03174(15) 0.00788(11) 0.00960(12) 0.00075(11) I4 0.01312(14) 0.02237(13) 0.03096(15) 0.00417(11) 0.00119(11) 0.00353(10) Ni1 0.0118(3) 0.0110(2) 0.0154(2) 0.00123(18) 0.00089(19) -0.00015(18) N1 0.0127(18) 0.0132(15) 0.0180(17) -0.0003(12) 0.0018(13) -0.0043(13) C1 0.018(2) 0.0118(18) 0.028(2) -0.0040(16) 0.0052(18) -0.0017(16) C2 0.024(3) 0.023(2) 0.028(2) -0.0066(18) 0.0111(19) -0.0060(18) C3 0.042(3) 0.031(2) 0.015(2) -0.0011(18) 0.003(2) -0.011(2) C4 0.030(3) 0.026(2) 0.017(2) 0.0012(17) -0.0016(19) -0.0022(18) C5 0.012(2) 0.0177(18) 0.020(2) -0.0017(15) -0.0028(16) -0.0068(15) C6 0.015(2) 0.0184(19) 0.018(2) -0.0003(16) -0.0011(16) -0.0001(16) N2 0.0109(17) 0.0119(15) 0.0175(16) -0.0015(12) 0.0010(13) -0.0015(12) C7 0.012(2) 0.0113(17) 0.021(2) -0.0027(14) 0.0020(16) 0.0005(15) C8 0.012(2) 0.0138(17) 0.0129(19) -0.0029(14) 0.0034(15) -0.0027(15) C9 0.015(2) 0.0143(18) 0.019(2) -0.0021(15) 0.0005(16) 0.0022(15) C10 0.021(2) 0.0108(17) 0.0153(19) 0.0034(14) 0.0018(16) -0.0026(15) C11 0.012(2) 0.0140(17) 0.019(2) -0.0009(15) 0.0056(16) -0.0037(15) C12 0.011(2) 0.0134(17) 0.016(2) 0.0013(14) -0.0016(15) -0.0007(14) C13 0.019(2) 0.0105(17) 0.0137(19) -0.0031(14) -0.0004(16) -0.0027(15) O1 0.0130(14) 0.0146(12) 0.0176(13) 0.0036(10) 0.0000(11) -0.0037(10) N3 0.0122(18) 0.0127(15) 0.0188(17) -0.0001(12) 0.0007(13) -0.0033(12) C14 0.024(2) 0.0128(18) 0.022(2) -0.0001(15) 0.0022(18) 0.0003(16) C15 0.028(3) 0.019(2) 0.023(2) 0.0002(16) 0.0110(18) -0.0019(17) C16 0.047(3) 0.021(2) 0.019(2) 0.0033(17) 0.009(2) -0.001(2) C17 0.037(3) 0.017(2) 0.019(2) 0.0061(16) 0.0004(19) -0.0026(18) C18 0.018(2) 0.0146(18) 0.018(2) -0.0014(15) -0.0030(17) -0.0022(15) C19 0.016(2) 0.0186(19) 0.022(2) 0.0053(16) -0.0041(17) 0.0007(16) N4 0.0109(17) 0.0125(15) 0.0206(17) 0.0019(12) 0.0031(13) -0.0026(12) C20 0.013(2) 0.0096(17) 0.025(2) 0.0012(15) 0.0045(16) 0.0020(15) C21 0.011(2) 0.0116(17) 0.018(2) -0.0034(14) 0.0002(15) 0.0000(14) C22 0.017(2) 0.0121(17) 0.023(2) 0.0007(15) -0.0013(17) 0.0028(15) C23 0.018(2) 0.0094(17) 0.024(2) 0.0032(15) 0.0039(17) -0.0019(15) C24 0.013(2) 0.0158(18) 0.020(2) -0.0015(15) 0.0066(15) -0.0034(15) C25 0.009(2) 0.0162(18) 0.020(2) -0.0007(15) -0.0010(15) 0.0020(15) C26 0.015(2) 0.0125(18) 0.017(2) -0.0055(14) 0.0034(16) -0.0017(15) O2 0.0127(14) 0.0140(13) 0.0176(13) 0.0033(10) -0.0007(11) -0.0026(10) C27 0.030(3) 0.0151(19) 0.022(2) -0.0005(16) 0.0000(18) 0.0012(17) Cl1 0.0274(6) 0.0340(6) 0.0292(6) -0.0066(5) -0.0087(5) 0.0041(5) Cl2 0.0291(7) 0.0381(6) 0.0613(8) 0.0137(6) 0.0042(6) -0.0064(5) Cl3 0.0571(9) 0.0244(6) 0.0609(8) 0.0029(5) 0.0202(7) 0.0139(6) C28 0.030(3) 0.021(2) 0.017(2) -0.0026(16) -0.0011(18) 0.0020(18) Cl4 0.0205(6) 0.0351(6) 0.0281(6) 0.0078(4) -0.0006(4) 0.0059(4) Cl5 0.0213(7) 0.0606(8) 0.0476(7) -0.0227(6) -0.0032(5) 0.0029(6) Cl6 0.0873(11) 0.0190(5) 0.0280(6) 0.0050(4) -0.0204(6) -0.0110(6) C29 0.029(3) 0.021(2) 0.024(2) -0.0013(17) 0.0002(18) -0.0045(18) Cl7 0.0302(7) 0.0251(5) 0.0327(6) -0.0075(4) -0.0071(5) 0.0008(4) Cl8 0.0395(8) 0.0268(6) 0.0537(8) -0.0135(5) 0.0110(6) -0.0016(5) Cl9 0.0525(9) 0.0579(8) 0.0321(6) 0.0100(6) -0.0163(6) -0.0104(6) _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 I1 C10 2.102(3) . ? I2 C12 2.089(3) . ? I3 C23 2.101(3) . ? I4 C25 2.112(3) . ? Ni1 O2 2.036(2) . ? Ni1 O1 2.057(2) . ? Ni1 N2 2.088(3) . ? Ni1 N3 2.090(3) . ? Ni1 N4 2.096(3) . ? Ni1 N1 2.098(3) . ? N1 C5 1.341(4) . ? N1 C1 1.342(5) . ? C1 C2 1.372(5) . ? C2 C3 1.388(5) . ? C3 C4 1.360(6) . ? C4 C5 1.393(5) . ? C5 C6 1.505(5) . ? C6 N2 1.477(4) . ? N2 C7 1.495(4) . ? C7 C8 1.499(5) . ? C8 C9 1.387(5) . ? C8 C13 1.432(5) . ? C9 C10 1.393(5) . ? C10 C11 1.390(5) . ? C11 C12 1.390(5) . ? C12 C13 1.406(5) . ? C13 O1 1.312(4) . ? N3 C14 1.340(5) . ? N3 C18 1.344(4) . ? C14 C15 1.377(5) . ? C15 C16 1.391(5) . ? C16 C17 1.390(6) . ? C17 C18 1.386(5) . ? C18 C19 1.506(5) . ? C19 N4 1.476(4) . ? N4 C20 1.492(4) . ? C20 C21 1.507(5) . ? C21 C22 1.387(5) . ? C21 C26 1.420(5) . ? C22 C23 1.373(5) . ? C23 C24 1.390(5) . ? C24 C25 1.386(5) . ? C25 C26 1.403(5) . ? C26 O2 1.315(4) . ? C27 Cl1 1.755(4) . ? C27 Cl2 1.757(4) . ? C27 Cl3 1.764(4) . ? C28 Cl5 1.746(4) . ? C28 Cl6 1.757(4) . ? C28 Cl4 1.763(4) . ? C29 Cl8 1.750(4) . ? C29 Cl9 1.752(4) . ? C29 Cl7 1.761(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Ni1 O1 179.52(10) . . ? O2 Ni1 N2 87.86(10) . . ? O1 Ni1 N2 91.99(10) . . ? O2 Ni1 N3 89.60(10) . . ? O1 Ni1 N3 90.87(10) . . ? N2 Ni1 N3 99.14(11) . . ? O2 Ni1 N4 92.66(10) . . ? O1 Ni1 N4 87.49(10) . . ? N2 Ni1 N4 179.47(11) . . ? N3 Ni1 N4 80.76(11) . . ? O2 Ni1 N1 88.86(10) . . ? O1 Ni1 N1 90.66(10) . . ? N2 Ni1 N1 81.01(11) . . ? N3 Ni1 N1 178.45(11) . . ? N4 Ni1 N1 99.10(12) . . ? C5 N1 C1 117.7(3) . . ? C5 N1 Ni1 113.3(3) . . ? C1 N1 Ni1 129.0(2) . . ? N1 C1 C2 123.9(4) . . ? C1 C2 C3 118.0(4) . . ? C4 C3 C2 118.8(4) . . ? C3 C4 C5 120.3(4) . . ? N1 C5 C4 121.3(4) . . ? N1 C5 C6 116.3(3) . . ? C4 C5 C6 122.4(3) . . ? N2 C6 C5 111.8(3) . . ? C6 N2 C7 113.2(3) . . ? C6 N2 Ni1 107.5(2) . . ? C7 N2 Ni1 112.1(2) . . ? N2 C7 C8 111.7(3) . . ? C9 C8 C13 120.9(3) . . ? C9 C8 C7 121.1(3) . . ? C13 C8 C7 118.0(3) . . ? C8 C9 C10 119.8(3) . . ? C11 C10 C9 121.3(3) . . ? C11 C10 I1 118.7(3) . . ? C9 C10 I1 119.9(3) . . ? C12 C11 C10 118.6(3) . . ? C11 C12 C13 122.7(3) . . ? C11 C12 I2 120.4(3) . . ? C13 C12 I2 116.9(2) . . ? O1 C13 C12 122.3(3) . . ? O1 C13 C8 120.9(3) . . ? C12 C13 C8 116.7(3) . . ? C13 O1 Ni1 115.7(2) . . ? C14 N3 C18 117.9(3) . . ? C14 N3 Ni1 128.2(2) . . ? C18 N3 Ni1 113.8(3) . . ? N3 C14 C15 124.0(3) . . ? C14 C15 C16 117.8(4) . . ? C15 C16 C17 119.0(4) . . ? C18 C17 C16 119.1(4) . . ? N3 C18 C17 122.1(4) . . ? N3 C18 C19 115.9(3) . . ? C17 C18 C19 122.0(3) . . ? N4 C19 C18 112.2(3) . . ? C19 N4 C20 113.9(3) . . ? C19 N4 Ni1 107.3(2) . . ? C20 N4 Ni1 111.9(2) . . ? N4 C20 C21 113.4(3) . . ? C22 C21 C26 120.5(3) . . ? C22 C21 C20 120.7(3) . . ? C26 C21 C20 118.7(3) . . ? C23 C22 C21 120.9(3) . . ? C22 C23 C24 120.9(3) . . ? C22 C23 I3 120.2(3) . . ? C24 C23 I3 118.9(3) . . ? C25 C24 C23 117.9(3) . . ? C24 C25 C26 123.6(3) . . ? C24 C25 I4 119.8(3) . . ? C26 C25 I4 116.6(2) . . ? O2 C26 C25 122.3(3) . . ? O2 C26 C21 121.5(3) . . ? C25 C26 C21 116.1(3) . . ? C26 O2 Ni1 117.9(2) . . ? Cl1 C27 Cl2 111.0(2) . . ? Cl1 C27 Cl3 110.5(2) . . ? Cl2 C27 Cl3 110.0(2) . . ? Cl5 C28 Cl6 110.8(2) . . ? Cl5 C28 Cl4 110.4(2) . . ? Cl6 C28 Cl4 109.7(2) . . ? Cl8 C29 Cl9 111.0(2) . . ? Cl8 C29 Cl7 110.8(2) . . ? Cl9 C29 Cl7 109.6(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.246 _refine_diff_density_min -0.890 _refine_diff_density_rms 0.153 #=== data_mndo _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H30 Cl6 I4 N4 O3 Zn' _chemical_formula_weight 1268.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 '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 orthorhombic _symmetry_space_group_name_H-M 'P212121' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 13.2593(4) _cell_length_b 15.4882(5) _cell_length_c 19.6143(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4028.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9945 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 24.2 _exptl_crystal_description 'needles' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.091 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2400 _exptl_absorpt_coefficient_mu 4.109 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3273 _exptl_absorpt_correction_T_max 0.8529 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 ? _diffrn_measurement_method 'Bruker APEX2' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 77377 _diffrn_reflns_av_R_equivalents 0.0733 _diffrn_reflns_av_sigmaI/netI 0.1233 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 34.56 _reflns_number_total 14082 _reflns_number_gt 8981 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker APEX2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-Plus _computing_publication_material SHELXL-97 _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^)+(0.0761P)^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 0.03(2) _refine_ls_number_reflns 14082 _refine_ls_number_parameters 419 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1187 _refine_ls_R_factor_gt 0.0633 _refine_ls_wR_factor_ref 0.1454 _refine_ls_wR_factor_gt 0.1318 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.40685(7) 0.70163(6) -0.02939(5) 0.01527(19) Uani 1 1 d . . . I1 I 0.53605(4) 1.04518(3) 0.22027(3) 0.02092(12) Uani 1 1 d . . . I2 I 0.27391(4) 0.72911(3) 0.20849(3) 0.02154(13) Uani 1 1 d . . . I3 I 0.50968(5) 0.25221(4) 0.11310(3) 0.02954(15) Uani 1 1 d . . . I4 I 0.24461(4) 0.42864(4) -0.09380(3) 0.02419(13) Uani 1 1 d . . . N1 N 0.3104(5) 0.7293(4) -0.1147(3) 0.0164(13) Uani 1 1 d . . . C1 C 0.2214(7) 0.6903(6) -0.1305(4) 0.0221(18) Uani 1 1 d . . . H1 H 0.2003 0.6424 -0.1038 0.026 Uiso 1 1 calc R . . C2 C 0.1609(6) 0.7168(6) -0.1829(4) 0.0221(18) Uani 1 1 d . . . H2 H 0.0991 0.6883 -0.1925 0.027 Uiso 1 1 calc R . . C3 C 0.1919(6) 0.7850(5) -0.2209(5) 0.0254(19) Uani 1 1 d . . . H3 H 0.1507 0.8054 -0.2571 0.030 Uiso 1 1 calc R . . C4 C 0.2845(6) 0.8259(6) -0.2072(4) 0.0229(18) Uani 1 1 d . . . H4 H 0.3077 0.8724 -0.2346 0.027 Uiso 1 1 calc R . . C5 C 0.3403(6) 0.7962(5) -0.1530(4) 0.0174(16) Uani 1 1 d . . . C6 C 0.4410(6) 0.8340(5) -0.1331(4) 0.0179(17) Uani 1 1 d . . . H6A H 0.4950 0.8031 -0.1580 0.021 Uiso 1 1 calc R . . H6B H 0.4431 0.8953 -0.1474 0.021 Uiso 1 1 calc R . . N2 N 0.4617(5) 0.8289(4) -0.0592(3) 0.0146(13) Uani 1 1 d . . . H2A H 0.5308 0.8328 -0.0513 0.017 Uiso 1 1 calc R . . C7 C 0.4085(6) 0.8991(5) -0.0226(4) 0.0163(16) Uani 1 1 d . . . H7A H 0.3364 0.8985 -0.0359 0.020 Uiso 1 1 calc R . . H7B H 0.4372 0.9553 -0.0368 0.020 Uiso 1 1 calc R . . C8 C 0.4163(6) 0.8911(5) 0.0535(4) 0.0156(16) Uani 1 1 d . . . C9 C 0.4641(6) 0.9526(5) 0.0903(4) 0.0133(14) Uani 1 1 d . . . H9 H 0.5004 0.9973 0.0679 0.016 Uiso 1 1 calc R . . C10 C 0.4597(6) 0.9500(5) 0.1629(4) 0.0172(16) Uani 1 1 d . . . C11 C 0.4081(6) 0.8869(5) 0.1953(4) 0.0199(17) Uani 1 1 d . . . H11 H 0.4043 0.8862 0.2436 0.024 Uiso 1 1 calc R . . C12 C 0.3601(6) 0.8223(6) 0.1569(4) 0.0190(17) Uani 1 1 d . . . C13 C 0.3645(6) 0.8215(5) 0.0857(4) 0.0159(16) Uani 1 1 d . . . O1 O 0.3222(4) 0.7601(3) 0.0492(3) 0.0154(11) Uani 1 1 d . . . N3 N 0.5219(5) 0.6312(4) -0.0936(4) 0.0184(14) Uani 1 1 d . . . C14 C 0.5071(7) 0.6043(6) -0.1575(4) 0.0241(18) Uani 1 1 d . . . H14 H 0.4511 0.6256 -0.1826 0.029 Uiso 1 1 calc R . . C15 C 0.5714(6) 0.5463(6) -0.1875(4) 0.0257(19) Uani 1 1 d . . . H15 H 0.5598 0.5278 -0.2330 0.031 Uiso 1 1 calc R . . C16 C 0.6539(7) 0.5144(7) -0.1513(5) 0.032(2) Uani 1 1 d . . . H16 H 0.6998 0.4752 -0.1718 0.039 Uiso 1 1 calc R . . C17 C 0.6668(6) 0.5407(6) -0.0860(5) 0.0227(18) Uani 1 1 d . . . H17 H 0.7204 0.5177 -0.0595 0.027 Uiso 1 1 calc R . . C18 C 0.6016(6) 0.6016(5) -0.0574(5) 0.0198(17) Uani 1 1 d . . . C19 C 0.6162(5) 0.6380(5) 0.0140(4) 0.0166(16) Uani 1 1 d . . . H19A H 0.6453 0.5925 0.0434 0.020 Uiso 1 1 calc R . . H19B H 0.6655 0.6860 0.0118 0.020 Uiso 1 1 calc R . . N4 N 0.5223(5) 0.6700(4) 0.0456(4) 0.0176(14) Uani 1 1 d . . . H4A H 0.5375 0.7199 0.0700 0.021 Uiso 1 1 calc R . . C20 C 0.4789(6) 0.6070(5) 0.0930(4) 0.0203(17) Uani 1 1 d . . . H20A H 0.4176 0.6325 0.1136 0.024 Uiso 1 1 calc R . . H20B H 0.5279 0.5971 0.1303 0.024 Uiso 1 1 calc R . . C21 C 0.4514(6) 0.5215(5) 0.0627(4) 0.0163(16) Uani 1 1 d . . . C22 C 0.4893(6) 0.4449(5) 0.0894(4) 0.0174(16) Uani 1 1 d . . . H22 H 0.5388 0.4467 0.1244 0.021 Uiso 1 1 calc R . . C23 C 0.4554(6) 0.3661(5) 0.0655(4) 0.0208(18) Uani 1 1 d . . . C24 C 0.3874(6) 0.3591(6) 0.0139(5) 0.0219(18) Uani 1 1 d . . . H24 H 0.3657 0.3043 -0.0022 0.026 Uiso 1 1 calc R . . C25 C 0.3510(6) 0.4350(5) -0.0144(4) 0.0175(16) Uani 1 1 d . . . C26 C 0.3772(6) 0.5170(5) 0.0097(4) 0.0161(16) Uani 1 1 d . . . O2 O 0.3359(4) 0.5871(4) -0.0160(3) 0.0178(12) Uani 1 1 d . . . C27 C 0.1920(8) 0.4666(9) 0.1397(6) 0.047(3) Uani 1 1 d . . . H27A H 0.2452 0.4224 0.1336 0.056 Uiso 1 1 calc R . . H27B H 0.2149 0.5201 0.1168 0.056 Uiso 1 1 calc R . . Cl1 Cl 0.0806(2) 0.4305(2) 0.10071(17) 0.0556(8) Uani 1 1 d . . . Cl2 Cl 0.1772(3) 0.4870(2) 0.22611(15) 0.0609(9) Uani 1 1 d . . . C28 C 0.2012(8) 0.8635(7) 0.3741(6) 0.042(3) Uani 1 1 d . . . H28A H 0.1421 0.8433 0.3477 0.050 Uiso 1 1 calc R . . H28B H 0.2560 0.8207 0.3680 0.050 Uiso 1 1 calc R . . Cl3 Cl 0.24108(18) 0.96365(16) 0.34189(12) 0.0342(5) Uani 1 1 d . . . Cl4 Cl 0.1690(3) 0.86887(19) 0.46027(16) 0.0579(9) Uani 1 1 d . . . C29 C 0.9191(9) 0.6973(9) 0.4103(6) 0.053(3) Uani 1 1 d . . . H29A H 0.9252 0.6403 0.4328 0.064 Uiso 1 1 calc R . . H29B H 0.9430 0.7421 0.4425 0.064 Uiso 1 1 calc R . . Cl5 Cl 0.7920(2) 0.7169(2) 0.38846(14) 0.0459(6) Uani 1 1 d . . . Cl6 Cl 0.9953(2) 0.6993(2) 0.33349(18) 0.0588(8) Uani 1 1 d . . . O3 O 0.1695(5) 0.6441(4) 0.0467(3) 0.0243(13) Uiso 1 1 d . . . H03A H 0.1846 0.6317 0.0030 0.050 Uiso 1 1 d . . . H03B H 0.2219 0.6771 0.0598 0.050 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 0.0081(4) 0.0192(5) 0.0185(5) 0.0012(4) -0.0010(3) -0.0002(3) I1 0.0205(3) 0.0227(3) 0.0196(3) -0.0036(2) 0.0014(2) -0.00205(19) I2 0.0170(3) 0.0252(3) 0.0225(3) 0.0028(2) 0.00488(19) -0.0026(2) I3 0.0285(3) 0.0232(3) 0.0369(3) 0.0057(3) -0.0072(2) 0.0051(2) I4 0.0176(3) 0.0250(3) 0.0299(3) -0.0022(2) -0.0086(2) -0.0016(2) N1 0.010(3) 0.016(3) 0.024(4) 0.000(3) -0.005(2) 0.002(2) C1 0.022(4) 0.024(5) 0.020(4) -0.001(3) -0.008(3) 0.000(3) C2 0.014(4) 0.028(5) 0.024(4) -0.011(4) 0.001(3) 0.000(3) C3 0.017(4) 0.024(5) 0.035(5) 0.000(4) -0.006(3) -0.004(3) C4 0.018(4) 0.033(5) 0.018(4) 0.004(4) -0.002(3) -0.003(3) C5 0.021(4) 0.013(4) 0.019(4) 0.000(3) 0.000(3) -0.001(3) C6 0.016(4) 0.019(4) 0.019(4) 0.001(3) 0.001(3) -0.001(3) N2 0.007(3) 0.023(4) 0.014(3) -0.001(3) -0.004(2) -0.003(2) C7 0.008(4) 0.012(4) 0.028(4) 0.005(3) 0.005(3) 0.005(3) C8 0.012(4) 0.015(4) 0.019(4) 0.003(3) -0.004(3) 0.003(3) C9 0.017(4) 0.008(3) 0.014(4) 0.005(3) 0.001(3) -0.001(3) C10 0.021(4) 0.019(4) 0.012(4) -0.001(3) 0.000(3) -0.001(3) C11 0.016(4) 0.024(5) 0.020(4) 0.000(4) 0.001(3) 0.005(3) C12 0.013(4) 0.023(5) 0.021(4) 0.001(3) 0.002(3) 0.000(3) C13 0.008(3) 0.019(4) 0.021(4) 0.003(3) -0.004(3) 0.002(3) O1 0.008(2) 0.015(3) 0.023(3) -0.002(2) -0.0029(19) -0.002(2) N3 0.010(3) 0.016(3) 0.029(4) 0.000(3) -0.003(3) 0.002(2) C14 0.024(5) 0.023(5) 0.025(5) -0.009(4) 0.000(3) 0.000(3) C15 0.019(4) 0.032(5) 0.026(5) -0.015(4) 0.002(3) 0.005(3) C16 0.017(5) 0.039(6) 0.041(6) -0.021(5) 0.004(4) 0.001(4) C17 0.010(4) 0.022(4) 0.036(5) -0.005(4) -0.001(3) 0.002(3) C18 0.015(4) 0.012(4) 0.033(5) -0.001(4) -0.003(3) 0.003(3) C19 0.004(3) 0.023(5) 0.022(4) 0.003(3) 0.004(3) 0.003(3) N4 0.007(3) 0.014(3) 0.031(4) 0.007(3) -0.009(3) 0.000(2) C20 0.013(4) 0.033(5) 0.015(4) 0.001(3) -0.004(3) -0.001(3) C21 0.009(4) 0.026(5) 0.013(4) 0.003(3) 0.001(3) -0.001(3) C22 0.008(3) 0.020(4) 0.024(4) -0.002(3) 0.001(3) -0.004(3) C23 0.018(4) 0.014(4) 0.031(5) 0.004(3) 0.006(3) 0.010(3) C24 0.014(4) 0.022(5) 0.030(5) -0.004(4) 0.005(3) 0.001(3) C25 0.020(4) 0.020(5) 0.012(4) 0.004(3) 0.002(3) 0.002(3) C26 0.012(4) 0.021(4) 0.015(4) 0.007(3) 0.004(3) -0.001(3) O2 0.004(2) 0.018(3) 0.031(3) 0.002(3) -0.002(2) 0.002(2) C27 0.016(5) 0.075(8) 0.049(7) 0.007(6) -0.003(4) 0.014(5) Cl1 0.0437(17) 0.0498(18) 0.073(2) 0.0025(16) -0.0241(15) 0.0047(13) Cl2 0.052(2) 0.094(3) 0.0366(16) 0.0085(16) 0.0021(13) -0.0228(17) C28 0.029(6) 0.031(6) 0.066(8) -0.005(5) 0.005(5) 0.007(4) Cl3 0.0259(12) 0.0416(13) 0.0352(12) 0.0036(10) -0.0010(9) 0.0005(10) Cl4 0.104(3) 0.0285(15) 0.0412(17) 0.0068(13) 0.0097(16) 0.0054(15) C29 0.043(7) 0.068(9) 0.048(7) -0.001(6) -0.016(6) 0.009(6) Cl5 0.0340(14) 0.0605(18) 0.0433(15) -0.0012(13) -0.0008(11) 0.0032(12) Cl6 0.0261(15) 0.068(2) 0.082(2) -0.0220(17) 0.0002(14) -0.0011(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 O2 2.025(6) . ? Zn1 O1 2.111(5) . ? Zn1 N1 2.149(6) . ? Zn1 N4 2.179(6) . ? Zn1 N2 2.181(7) . ? Zn1 N3 2.259(7) . ? I1 C10 2.113(8) . ? I2 C12 2.101(8) . ? I3 C23 2.122(8) . ? I4 C25 2.104(8) . ? N1 C5 1.339(10) . ? N1 C1 1.362(10) . ? C1 C2 1.367(12) . ? C2 C3 1.356(13) . ? C3 C4 1.407(11) . ? C4 C5 1.376(11) . ? C5 C6 1.509(11) . ? C6 N2 1.477(10) . ? N2 C7 1.482(10) . ? C7 C8 1.503(12) . ? C8 C9 1.353(11) . ? C8 C13 1.426(11) . ? C9 C10 1.426(10) . ? C10 C11 1.352(12) . ? C11 C12 1.404(12) . ? C12 C13 1.397(12) . ? C13 O1 1.316(9) . ? N3 C14 1.336(11) . ? N3 C18 1.353(10) . ? C14 C15 1.371(12) . ? C15 C16 1.395(13) . ? C16 C17 1.354(13) . ? C17 C18 1.397(11) . ? C18 C19 1.521(12) . ? C19 N4 1.477(10) . ? N4 C20 1.465(10) . ? C20 C21 1.496(11) . ? C21 C22 1.391(11) . ? C21 C26 1.433(11) . ? C22 C23 1.382(12) . ? C23 C24 1.360(12) . ? C24 C25 1.387(12) . ? C25 C26 1.399(12) . ? C26 O2 1.317(10) . ? C27 Cl2 1.734(11) . ? C27 Cl1 1.755(11) . ? C28 Cl4 1.746(12) . ? C28 Cl3 1.757(11) . ? C29 Cl5 1.765(12) . ? C29 Cl6 1.814(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Zn1 O1 92.0(2) . . ? O2 Zn1 N1 90.0(2) . . ? O1 Zn1 N1 99.6(2) . . ? O2 Zn1 N4 92.4(2) . . ? O1 Zn1 N4 88.7(2) . . ? N1 Zn1 N4 171.3(3) . . ? O2 Zn1 N2 168.9(2) . . ? O1 Zn1 N2 89.2(2) . . ? N1 Zn1 N2 79.0(2) . . ? N4 Zn1 N2 98.6(2) . . ? O2 Zn1 N3 87.9(2) . . ? O1 Zn1 N3 166.7(2) . . ? N1 Zn1 N3 93.7(2) . . ? N4 Zn1 N3 78.1(3) . . ? N2 Zn1 N3 93.5(2) . . ? C5 N1 C1 118.2(7) . . ? C5 N1 Zn1 114.5(5) . . ? C1 N1 Zn1 127.2(5) . . ? N1 C1 C2 123.1(8) . . ? C3 C2 C1 118.0(8) . . ? C2 C3 C4 120.6(8) . . ? C5 C4 C3 117.8(8) . . ? N1 C5 C4 122.2(8) . . ? N1 C5 C6 114.7(7) . . ? C4 C5 C6 123.1(7) . . ? N2 C6 C5 113.4(6) . . ? C6 N2 C7 110.3(6) . . ? C6 N2 Zn1 104.4(5) . . ? C7 N2 Zn1 112.0(5) . . ? N2 C7 C8 112.8(6) . . ? C9 C8 C13 121.5(7) . . ? C9 C8 C7 120.3(7) . . ? C13 C8 C7 118.0(7) . . ? C8 C9 C10 119.5(7) . . ? C11 C10 C9 120.7(8) . . ? C11 C10 I1 119.8(6) . . ? C9 C10 I1 119.5(6) . . ? C10 C11 C12 119.5(8) . . ? C13 C12 C11 121.6(8) . . ? C13 C12 I2 119.9(6) . . ? C11 C12 I2 118.5(6) . . ? O1 C13 C12 122.2(7) . . ? O1 C13 C8 120.7(7) . . ? C12 C13 C8 117.1(7) . . ? C13 O1 Zn1 118.8(5) . . ? C14 N3 C18 120.1(7) . . ? C14 N3 Zn1 125.1(6) . . ? C18 N3 Zn1 113.5(6) . . ? N3 C14 C15 121.0(8) . . ? C14 C15 C16 120.1(8) . . ? C17 C16 C15 118.3(8) . . ? C16 C17 C18 120.3(8) . . ? N3 C18 C17 120.0(8) . . ? N3 C18 C19 117.2(7) . . ? C17 C18 C19 122.7(7) . . ? N4 C19 C18 113.8(6) . . ? C20 N4 C19 112.0(6) . . ? C20 N4 Zn1 107.6(5) . . ? C19 N4 Zn1 112.6(5) . . ? N4 C20 C21 115.7(7) . . ? C22 C21 C26 118.6(7) . . ? C22 C21 C20 121.2(7) . . ? C26 C21 C20 119.9(7) . . ? C23 C22 C21 120.6(7) . . ? C24 C23 C22 122.6(8) . . ? C24 C23 I3 119.1(6) . . ? C22 C23 I3 118.3(6) . . ? C23 C24 C25 117.4(8) . . ? C24 C25 C26 123.2(7) . . ? C24 C25 I4 119.3(6) . . ? C26 C25 I4 117.4(6) . . ? O2 C26 C25 121.0(7) . . ? O2 C26 C21 121.6(7) . . ? C25 C26 C21 117.4(7) . . ? C26 O2 Zn1 125.3(5) . . ? Cl2 C27 Cl1 112.9(6) . . ? Cl4 C28 Cl3 112.3(6) . . ? Cl5 C29 Cl6 109.1(6) . . ? _diffrn_measured_fraction_theta_max 0.853 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 2.032 _refine_diff_density_min -2.571 _refine_diff_density_rms 0.270 #===end