# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1732 data_zn8nofinabs1 _audit_creation_method SHELXL _publ_requested_journal 'test' _publ_contact_author ; K.M. Barkigia (regarding crystallographic details and this CIF) Energy Sciences and Technology Department Bldg. 555 Brookhaven National Laboratory Upton, NY 11973 USA ; _publ_contact_author_email 'barkigia@bnl.gov' _publ_contact_author_fax '631-344-5815' _publ_contact_author_phone '631-344-7661' _publ_contact_letter ; This CIF corresponds to manuscript number B004160M, which has been submitted to ChemComm. ; _publ_section_title ; A New General Method for Selective beta-Polynitration of Porphyrins; Preparation and Redox Properties of Zn-Porphyrins Bearing One Through Eight beta-Nitro Substituents and X-Ray Structure of the First Zn beta-Pernitro Porphyrin. ; loop_ _publ_author_name _publ_author_address 'Palacio, Magali' ; URA 400 Universite Paris V 45 rue des Saints-Peres 75270 Paris Cedex 06 France ; 'Mansuy-Mouries, Virginie' ; URA 400 Universite Paris V 45 rue des Saints-Peres 75270 Paris Cedex 06 France ; 'Loire, Guillaume' ; URA 400 Universite Paris V 45 rue des Saints-Peres 75270 Paris Cedex 06 France ; 'Le Barch-Ozette, Karine' ; URA 400 Universite Paris V 45 rue des Saints-Peres 75270 Paris Cedex 06 France ; 'Leduc, Philippe' ; URA 400 Universite Paris V 45 rue des Saints-Peres 75270 Paris Cedex 06 France ; 'Barkigia, Kathleen M.' ; Department of Applied Science Bldg. 555 Brookhaven National Laboratory Upton, NY 11973 USA ; 'Fajer, Jack' ; Department of Applied Science Bldg. 815 Brookhaven National Laboratory Upton, NY 11973 USA ; 'Battioni, Pierrette' ; URA 400 Universite Paris V 45 ru des Saints-Peres 75270 Paris Cedex 06 France ; 'Mansuy, Daniel' ; URA 400 Universite Paris V 45 ru des Saints-Peres 75270 Paris Cedex 06 France ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural 'C44 H12 Cl8 N12 O16 Zn, 2(C2 H5 OH), 2(C2 H5 OH)' _chemical_formula_analytical ? _chemical_formula_sum 'C52 H36 Cl8 N12 O20 Zn' _chemical_formula_weight 1497.90 _chemical_melting_point ? _chemical_compound_source 'methylene chloride' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Zn' 'Zn' -1.5491 0.6778 '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 11.792(3) _cell_length_b 11.993(2) _cell_length_c 12.279(4) _cell_angle_alpha 106.04(2) _cell_angle_beta 90.24(3) _cell_angle_gamma 106.87(3) _cell_volume 1590.4(7) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 25 _exptl_crystal_description 'block' _exptl_crystal_colour 'dark blue' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method ? _exptl_crystal_F_000 758. _exptl_absorpt_coefficient_mu 4.343 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.2851 _exptl_absorpt_correction_T_max 0.5966 _exptl_absorpt_process_details ; The faces of the crystal were indexed, and the face-indexed absorption correction program in the SHELXTL package was used. ; _exptl_special_details ; After surveying several crystals which were completely amorphous, data was collected on this crystal, in spite of omega scans which had widths of 0.5 degrees. It did not diffract beyond 55 degrees in theta. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius CAD4' _diffrn_measurement_method '\q/2\q' _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% none _diffrn_reflns_number 4210 _diffrn_reflns_av_R_equivalents 0.0911 _diffrn_reflns_av_sigmaI/netI 0.1332 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.76 _diffrn_reflns_theta_max 55.06 _reflns_number_total 3973 _reflns_number_gt 1938 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4_(Enraf-Nonius,_1977)' _computing_cell_refinement 'CAD4_(Enraf-Nonius,_1977)' _computing_data_reduction 'XCAD4VAX provided with SHELXL-93' _computing_structure_solution 'SIR92 (Burla et al., 1994)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL and other in house programs' _computing_publication_material 'CIFTAB provided with SHELXS-86' _publ_section_references ; Altomare, A.M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G., Camalli, M. (1994). SIR92. J. Appl. Cryst. 27, 435-436. Enraf-Nonius, CAD4 Operations Manual, Delft, 1977. International Tables for Crystallography (1992). Vol. C. Dordrecht: Kluwer Academic Publishers. Sheldrick, G.M. (1993). SHELXL93. Program for the Refinment of Crystal Structures. University of Gottingen, Germany. Siemens, SHELXTL Version 5 Reference Manual, 1994. ; _refine_special_details ; Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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. The hydroxyl hydrogens of the axial ethanols and those associated with the disordered ethanols of solvation were not included in the model. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1842P)^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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3971 _refine_ls_number_parameters 439 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2087 _refine_ls_R_factor_obs 0.0936 _refine_ls_wR_factor_all 0.3169 _refine_ls_wR_factor_obs 0.2343 _refine_ls_goodness_of_fit_all 1.031 _refine_ls_goodness_of_fit_obs 1.180 _refine_ls_restrained_S_all 1.063 _refine_ls_restrained_S_obs 1.180 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Zn Zn -1.0000 0.0000 -1.0000 0.0527(8) Uani 1 d S . Cl1 Cl -1.1206(6) -0.4826(4) -1.2340(5) 0.154(2) Uani 1 d . . Cl2 Cl -1.3037(5) -0.2002(4) -1.4031(4) 0.132(2) Uani 1 d . . Cl3 Cl -0.5965(6) -0.0948(6) -1.1695(7) 0.202(4) Uani 1 d . . Cl4 Cl -0.7215(4) 0.2659(5) -1.2606(5) 0.135(2) Uani 1 d . . O1 O -1.5035(12) -0.3677(11) -0.9583(14) 0.167(7) Uani 1 d . . O2 O -1.5408(11) -0.2141(17) -0.9783(11) 0.141(6) Uani 1 d . . O3 O -1.4092(14) -0.4851(13) -1.2057(10) 0.159(7) Uani 1 d . . O4 O -1.4924(12) -0.3692(17) -1.2473(12) 0.168(8) Uani 1 d . . O5 O -1.0019(12) -0.3763(12) -1.4726(11) 0.146(6) Uani 1 d . . O6 O -1.0582(15) -0.2490(14) -1.5274(11) 0.163(7) Uani 1 d . . O7 O -0.7424(15) -0.1651(12) -1.4452(17) 0.226(12) Uani 1 d . . O8 O -0.7922(11) -0.0141(16) -1.4585(9) 0.159(7) Uani 1 d . . O9 O -0.9256(9) -0.1292(8) -0.9389(9) 0.088(3) Uani 1 d . . N1 N -1.1681(7) -0.1282(8) -1.0324(7) 0.052(2) Uani 1 d . . N2 N -0.9628(7) -0.0774(7) -1.1630(7) 0.050(2) Uani 1 d . . N3 N -1.4774(11) -0.2757(13) -0.9782(9) 0.079(4) Uani 1 d . . N4 N -1.4178(12) -0.3849(15) -1.1973(10) 0.092(5) Uani 1 d . . N5 N -1.0168(12) -0.2797(12) -1.4576(10) 0.088(4) Uani 1 d . . N6 N -0.7918(13) -0.0971(14) -1.4152(11) 0.116(6) Uani 1 d . . C1 C -1.2546(9) -0.1330(9) -0.9577(8) 0.054(3) Uani 1 d . . C2 C -1.3592(9) -0.2303(10) -1.0151(9) 0.054(3) Uani 1 d . . C3 C -1.3314(9) -0.2832(9) -1.1193(8) 0.054(3) Uani 1 d . . C4 C -1.2117(9) -0.2181(9) -1.1323(8) 0.048(3) Uani 1 d . . C5 C -1.1519(8) -0.2419(9) -1.2303(8) 0.042(3) Uani 1 d . . C6 C -1.0375(9) -0.1731(9) -1.2415(8) 0.047(3) Uani 1 d . . C7 C -0.9758(10) -0.1921(9) -1.3474(8) 0.053(3) Uani 1 d . . C8 C -0.8697(10) -0.1079(10) -1.3253(8) 0.061(4) Uani 1 d . . C9 C -0.8553(9) -0.0338(9) -1.2095(9) 0.048(3) Uani 1 d . . C10 C -0.7586(9) 0.0612(9) -1.1549(7) 0.048(3) Uani 1 d . . C11 C -1.2160(9) -0.3494(9) -1.3278(9) 0.049(3) Uani 1 d . . C12 C -1.2054(10) -0.4606(11) -1.3371(10) 0.068(4) Uani 1 d . . C13 C -1.2633(14) -0.5618(12) -1.4283(16) 0.095(5) Uani 1 d . . H13 H -1.2543(14) -0.6373(12) -1.4325(16) 0.113 Uiso 1 calc R . C14 C -1.3324(13) -0.5505(15) -1.5106(12) 0.080(4) Uani 1 d . . H14 H -1.3714(13) -0.6176(15) -1.5712(12) 0.096 Uiso 1 calc R . C15 C -1.3434(12) -0.4393(14) -1.5025(10) 0.076(4) Uani 1 d . . H15 H -1.3909(12) -0.4300(14) -1.5580(10) 0.091 Uiso 1 calc R . C16 C -1.2843(11) -0.3384(11) -1.4119(10) 0.064(4) Uani 1 d . . C17 C -0.6517(10) 0.0847(10) -1.2230(9) 0.057(3) Uani 1 d . . C18 C -0.5753(13) 0.0164(13) -1.2317(13) 0.086(4) Uani 1 d . . C19 C -0.4790(15) 0.0396(17) -1.3020(18) 0.132(8) Uani 1 d . . H19 H -0.4296(15) -0.0098(17) -1.3155(18) 0.158 Uiso 1 calc R . C20 C -0.4598(15) 0.1319(18) -1.3484(12) 0.099(6) Uani 1 d . . H20 H -0.3944(15) 0.1480(18) -1.3900(12) 0.119 Uiso 1 calc R . C21 C -0.5318(14) 0.2009(16) -1.3365(12) 0.095(5) Uani 1 d . . H21 H -0.5175(14) 0.2643(16) -1.3693(12) 0.114 Uiso 1 calc R . C22 C -0.6295(10) 0.1759(13) -1.2734(10) 0.074(4) Uani 1 d . . C23 C -0.8480(28) -0.1044(20) -0.8392(17) 0.183(12) Uani 1 d . . H23A H -0.7785(28) -0.1295(20) -0.8625(17) 0.219 Uiso 1 calc R . H23B H -0.8209(28) -0.0171(20) -0.8035(17) 0.219 Uiso 1 calc R . C24 C -0.8980(23) -0.1610(25) -0.7585(19) 0.205(13) Uani 1 d . . H24A H -0.8400(23) -0.1394(25) -0.6951(19) 0.308 Uiso 1 calc R . H24B H -0.9230(23) -0.2477(25) -0.7919(19) 0.308 Uiso 1 calc R . H24C H -0.9655(23) -0.1351(25) -0.7328(19) 0.308 Uiso 1 calc R . O10 O -1.1455(19) 0.2913(20) -0.8990(21) 0.105(8) Uani 0.50 d P . O11 O -1.1989(21) 0.4296(26) -0.7656(23) 0.151(10) Uani 0.50 d P . C25 C -1.1718(17) 0.3914(31) -0.8855(22) 0.174(13) Uani 1 d . . C26 C -1.1747(47) 0.5006(62) -0.9416(49) 0.163(21) Uani 0.50 d P . C27 C -1.1296(52) 0.3838(80) -0.9706(34) 0.256(50) Uani 0.50 d P . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn 0.0558(14) 0.0546(13) 0.0303(11) 0.0052(10) 0.0282(10) -0.0029(10) Cl1 0.202(6) 0.088(3) 0.157(5) 0.008(3) -0.061(4) 0.050(3) Cl2 0.202(5) 0.087(3) 0.100(3) 0.009(2) -0.028(3) 0.052(3) Cl3 0.210(6) 0.177(5) 0.334(9) 0.175(6) 0.180(6) 0.133(5) Cl4 0.124(4) 0.163(4) 0.176(5) 0.117(4) 0.081(3) 0.067(3) O1 0.171(13) 0.090(8) 0.240(17) 0.074(10) 0.145(12) 0.015(8) O2 0.086(9) 0.261(17) 0.127(10) 0.111(11) 0.060(8) 0.077(10) O3 0.218(16) 0.084(9) 0.086(8) -0.010(7) 0.047(9) -0.054(10) O4 0.085(9) 0.256(19) 0.106(11) -0.040(11) -0.022(8) 0.057(11) O5 0.160(12) 0.102(9) 0.132(11) -0.047(8) 0.034(8) 0.048(9) O6 0.210(16) 0.151(13) 0.064(8) 0.031(8) -0.006(9) -0.041(10) O7 0.222(17) 0.088(9) 0.292(21) -0.012(11) 0.225(17) -0.004(9) O8 0.125(10) 0.224(16) 0.071(7) 0.060(9) 0.030(6) -0.049(10) O9 0.105(7) 0.084(7) 0.079(7) 0.027(5) 0.024(6) 0.030(5) N1 0.041(5) 0.065(6) 0.040(5) 0.011(5) 0.025(4) 0.003(4) N2 0.056(6) 0.048(5) 0.037(5) 0.013(4) 0.024(4) 0.003(4) N3 0.073(9) 0.095(10) 0.053(6) 0.016(6) 0.032(6) 0.005(7) N4 0.079(10) 0.110(11) 0.046(7) -0.002(8) 0.030(7) -0.009(9) N5 0.107(10) 0.073(9) 0.048(7) -0.012(7) 0.053(7) -0.001(7) N6 0.123(11) 0.090(10) 0.076(9) -0.003(8) 0.078(8) -0.032(9) C1 0.059(7) 0.051(7) 0.034(6) 0.007(5) 0.027(5) -0.004(5) C2 0.049(7) 0.061(7) 0.044(6) 0.019(6) 0.026(5) 0.000(6) C3 0.052(7) 0.045(6) 0.034(6) -0.001(5) 0.016(5) -0.020(5) C4 0.050(7) 0.057(7) 0.022(5) 0.001(5) 0.018(5) 0.003(5) C5 0.039(6) 0.041(6) 0.031(5) 0.002(5) 0.017(5) -0.002(5) C6 0.049(7) 0.041(6) 0.022(5) -0.013(5) 0.018(5) -0.008(5) C7 0.074(8) 0.049(7) 0.019(5) -0.005(5) 0.025(5) 0.009(6) C8 0.066(8) 0.057(7) 0.035(6) -0.002(5) 0.034(6) -0.008(6) C9 0.045(6) 0.045(6) 0.051(6) 0.018(5) 0.030(5) 0.006(5) C10 0.055(7) 0.048(6) 0.023(5) 0.006(5) 0.028(5) -0.007(5) C11 0.050(7) 0.038(7) 0.037(6) -0.002(5) 0.018(6) -0.007(5) C12 0.058(8) 0.055(8) 0.066(8) -0.006(7) 0.002(6) 0.003(6) C13 0.081(11) 0.054(9) 0.116(13) -0.007(9) 0.020(10) 0.002(8) C14 0.079(11) 0.080(11) 0.049(8) -0.009(8) 0.012(7) 0.002(8) C15 0.088(10) 0.083(10) 0.039(7) 0.000(7) 0.010(7) 0.016(8) C16 0.067(8) 0.070(8) 0.040(7) 0.004(6) 0.014(6) 0.007(6) C17 0.061(8) 0.058(7) 0.048(7) 0.017(6) 0.038(6) 0.008(6) C18 0.090(10) 0.083(10) 0.103(11) 0.037(8) 0.055(9) 0.041(8) C19 0.105(13) 0.120(14) 0.188(20) 0.046(15) 0.099(14) 0.057(11) C20 0.083(12) 0.133(15) 0.061(9) 0.029(9) 0.046(8) 0.001(11) C21 0.088(11) 0.133(14) 0.068(9) 0.056(10) 0.051(9) 0.013(10) C22 0.059(8) 0.099(10) 0.061(8) 0.038(8) 0.032(6) 0.006(7) C23 0.365(39) 0.131(18) 0.086(14) 0.036(14) 0.030(20) 0.123(22) C24 0.245(29) 0.242(29) 0.114(17) 0.101(20) 0.031(18) 0.003(23) O10 0.092(15) 0.093(15) 0.111(17) -0.024(14) 0.030(13) 0.051(13) O11 0.115(19) 0.179(25) 0.145(23) 0.017(20) 0.066(17) 0.052(18) C25 0.086(14) 0.195(27) 0.155(24) -0.085(21) 0.006(14) 0.043(16) C26 0.161(45) 0.231(59) 0.124(41) 0.078(43) 0.070(32) 0.074(42) C27 0.179(52) 0.319(81) 0.050(21) -0.057(37) 0.047(28) -0.151(57) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn N2 2.068(8) 2_353 ? Zn N2 2.068(8) . ? Zn N1 2.083(8) 2_353 ? Zn N1 2.083(8) . ? Zn O9 2.272(10) 2_353 ? Zn O9 2.272(10) . ? Cl1 C12 1.732(14) . ? Cl2 C16 1.713(14) . ? Cl3 C18 1.67(2) . ? Cl4 C22 1.720(15) . ? O1 N3 1.15(2) . ? O2 N3 1.19(2) . ? O3 N4 1.21(2) . ? O4 N4 1.16(2) . ? O5 N5 1.19(2) . ? O6 N5 1.18(2) . ? O7 N6 1.12(2) . ? O8 N6 1.25(2) . ? O9 C23 1.43(2) . ? N1 C4 1.369(12) . ? N1 C1 1.374(12) . ? N2 C6 1.348(11) . ? N2 C9 1.411(12) . ? N3 C2 1.465(14) . ? N4 C3 1.44(2) . ? N5 C7 1.443(14) . ? N6 C8 1.448(14) . ? C1 C10 1.393(13) 2_353 ? C1 C2 1.443(14) . ? C2 C3 1.350(13) . ? C3 C4 1.435(13) . ? C4 C5 1.400(12) . ? C5 C6 1.392(12) . ? C5 C11 1.497(13) . ? C6 C7 1.489(12) . ? C7 C8 1.331(14) . ? C8 C9 1.434(14) . ? C9 C10 1.365(13) . ? C10 C1 1.393(13) 2_353 ? C10 C17 1.517(13) . ? C11 C12 1.35(2) . ? C11 C16 1.37(2) . ? C12 C13 1.40(2) . ? C13 C14 1.35(2) . ? C14 C15 1.35(2) . ? C15 C16 1.40(2) . ? C17 C22 1.36(2) . ? C17 C18 1.37(2) . ? C18 C19 1.44(2) . ? C19 C20 1.34(2) . ? C20 C21 1.33(2) . ? C21 C22 1.40(2) . ? C23 C24 1.39(3) . ? O10 C25 1.29(4) . ? O11 C25 1.48(3) . ? C25 C27 1.15(4) . ? C25 C26 1.65(6) . ? 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 N2 Zn N2 180.000(2) 2_353 . ? N2 Zn N1 89.4(3) 2_353 2_353 ? N2 Zn N1 90.6(3) . 2_353 ? N2 Zn N1 90.6(3) 2_353 . ? N2 Zn N1 89.4(3) . . ? N1 Zn N1 180.0 2_353 . ? N2 Zn O9 88.8(3) 2_353 2_353 ? N2 Zn O9 91.2(3) . 2_353 ? N1 Zn O9 90.0(4) 2_353 2_353 ? N1 Zn O9 90.0(4) . 2_353 ? N2 Zn O9 91.2(3) 2_353 . ? N2 Zn O9 88.8(3) . . ? N1 Zn O9 90.0(4) 2_353 . ? N1 Zn O9 90.0(4) . . ? O9 Zn O9 179.998(3) 2_353 . ? C23 O9 Zn 129.0(10) . . ? C4 N1 C1 109.1(8) . . ? C4 N1 Zn 125.7(6) . . ? C1 N1 Zn 125.1(7) . . ? C6 N2 C9 110.0(8) . . ? C6 N2 Zn 125.7(6) . . ? C9 N2 Zn 124.3(6) . . ? O1 N3 O2 126.1(14) . . ? O1 N3 C2 119.1(15) . . ? O2 N3 C2 114.6(13) . . ? O4 N4 O3 123.0(17) . . ? O4 N4 C3 120.1(19) . . ? O3 N4 C3 116.9(17) . . ? O6 N5 O5 124.6(14) . . ? O6 N5 C7 118.0(16) . . ? O5 N5 C7 117.3(16) . . ? O7 N6 O8 125.1(15) . . ? O7 N6 C8 119.6(19) . . ? O8 N6 C8 115.2(17) . . ? N1 C1 C10 126.0(9) . 2_353 ? N1 C1 C2 107.6(8) . . ? C10 C1 C2 126.3(9) 2_353 . ? C3 C2 C1 107.3(8) . . ? C3 C2 N3 121.0(9) . . ? C1 C2 N3 131.7(9) . . ? C2 C3 C4 108.4(8) . . ? C2 C3 N4 120.7(9) . . ? C4 C3 N4 130.9(9) . . ? N1 C4 C5 126.7(8) . . ? N1 C4 C3 107.5(8) . . ? C5 C4 C3 125.8(9) . . ? C6 C5 C4 124.2(8) . . ? C6 C5 C11 118.8(8) . . ? C4 C5 C11 117.1(8) . . ? N2 C6 C5 128.3(8) . . ? N2 C6 C7 106.9(8) . . ? C5 C6 C7 124.8(8) . . ? C8 C7 N5 123.0(9) . . ? C8 C7 C6 107.1(8) . . ? N5 C7 C6 129.9(9) . . ? C7 C8 C9 110.0(8) . . ? C7 C8 N6 120.2(9) . . ? C9 C8 N6 129.7(9) . . ? C10 C9 N2 126.6(9) . . ? C10 C9 C8 127.4(8) . . ? N2 C9 C8 106.0(8) . . ? C9 C10 C1 127.1(8) . 2_353 ? C9 C10 C17 115.8(8) . . ? C1 C10 C17 117.0(8) 2_353 . ? C12 C11 C16 117.5(10) . . ? C12 C11 C5 120.8(12) . . ? C16 C11 C5 121.6(11) . . ? C11 C12 C13 121.6(14) . . ? C11 C12 Cl1 120.5(9) . . ? C13 C12 Cl1 117.8(13) . . ? C14 C13 C12 120.5(15) . . ? C15 C14 C13 118.5(13) . . ? C14 C15 C16 120.7(14) . . ? C11 C16 C15 121.1(13) . . ? C11 C16 Cl2 119.6(9) . . ? C15 C16 Cl2 119.2(12) . . ? C22 C17 C18 119.7(11) . . ? C22 C17 C10 120.2(12) . . ? C18 C17 C10 120.1(11) . . ? C17 C18 C19 117.2(14) . . ? C17 C18 Cl3 121.8(10) . . ? C19 C18 Cl3 120.9(13) . . ? C20 C19 C18 120.7(16) . . ? C21 C20 C19 121.8(14) . . ? C20 C21 C22 118.4(15) . . ? C17 C22 C21 122.0(15) . . ? C17 C22 Cl4 120.7(9) . . ? C21 C22 Cl4 117.3(13) . . ? C24 C23 O9 115.2(25) . . ? C27 C25 O11 165.1(34) . . ? O10 C25 C26 146.0(31) . . ? _refine_diff_density_max 0.993 _refine_diff_density_min -1.051 _refine_diff_density_rms 0.118 #===END