# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Michael Watkinson' _publ_contact_author_address ; Mile End Road London E1 4NS ; _publ_contact_author_email m.watkinson@qmul.ac.uk loop_ _publ_author_name K.Jobe C.Brennan M.Motevalli S.Goldup 'Michael Watkinson' # Attachment '- final-cif-for hjcyzn3r-R2.cif' data_cu_kjcyzn3r_0m _database_code_depnum_ccdc_archive 'CCDC 815162' #TrackingRef '- final-cif-for hjcyzn3r-R2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H32 N8 O2 Zn, Cl O4, C2 H3 N, Cl O4' _chemical_formula_sum 'C27 H35 Cl2 N9 O10 Zn' _chemical_formula_weight 781.91 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' _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 12.2193(2) _cell_length_b 12.3857(2) _cell_length_c 42.4545(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.6920(10) _cell_angle_gamma 90.00 _cell_volume 6424.79(19) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9983 _cell_measurement_theta_min 5.08 _cell_measurement_theta_max 66.64 _exptl_crystal_description shard _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.617 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3232 _exptl_absorpt_coefficient_mu 3.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5125 _exptl_absorpt_correction_T_max 0.7393 _exptl_absorpt_process_details ; SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction ; _diffrn_ambient_temperature 100(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_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 69974 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_sigmaI/netI 0.0177 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 50 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 67.27 _reflns_number_total 5633 _reflns_number_gt 5562 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2\s(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^)+(0.0235P)^2^+52.7250P] 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 5633 _refine_ls_number_parameters 464 _refine_ls_number_restraints 40 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0637 _refine_ls_wR_factor_ref 0.1422 _refine_ls_wR_factor_gt 0.1420 _refine_ls_goodness_of_fit_ref 1.322 _refine_ls_restrained_S_all 1.343 _refine_ls_shift/su_max 0.002 _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 C1 C 0.1779(4) 0.3930(4) 0.59013(11) 0.0292(10) Uani 1 1 d . . . H1 H 0.1656 0.4608 0.5803 0.035 Uiso 1 1 calc R . . C2 C 0.2211(4) 0.3743(4) 0.61936(10) 0.0246(9) Uani 1 1 d . . . C3 C 0.2635(4) 0.4462(4) 0.64508(10) 0.0253(10) Uani 1 1 d . . . H3A H 0.3411 0.4646 0.6412 0.030 Uiso 1 1 calc R . . H3B H 0.2208 0.5141 0.6455 0.030 Uiso 1 1 calc R . . C4 C 0.1460(4) 0.4090(4) 0.68977(11) 0.0253(10) Uani 1 1 d . . . H4A H 0.0911 0.4202 0.6728 0.030 Uiso 1 1 calc R . . H4B H 0.1492 0.4755 0.7027 0.030 Uiso 1 1 calc R . . C5 C 0.1111(4) 0.3155(4) 0.71010(11) 0.0243(9) Uani 1 1 d . . . H5A H 0.1625 0.3072 0.7282 0.029 Uiso 1 1 calc R . . H5B H 0.0370 0.3289 0.7184 0.029 Uiso 1 1 calc R . . C6 C 0.0960(4) 0.1164(4) 0.70841(12) 0.0303(10) Uani 1 1 d . . . H6A H 0.0634 0.0607 0.6945 0.036 Uiso 1 1 calc R . . H6B H 0.0453 0.1291 0.7260 0.036 Uiso 1 1 calc R . . C7 C 0.2054(4) 0.0771(4) 0.72120(11) 0.0282(10) Uani 1 1 d . . . H7A H 0.2341 0.1285 0.7371 0.034 Uiso 1 1 calc R . . H7B H 0.1964 0.0058 0.7314 0.034 Uiso 1 1 calc R . . C8 C 0.3976(4) 0.0609(4) 0.70514(12) 0.0328(11) Uani 1 1 d . . . H8A H 0.4409 0.0246 0.6887 0.039 Uiso 1 1 calc R . . H8B H 0.4033 0.0176 0.7247 0.039 Uiso 1 1 calc R . . C9 C 0.4426(4) 0.1732(4) 0.71102(11) 0.0281(10) Uani 1 1 d . . . H9A H 0.4035 0.2074 0.7287 0.034 Uiso 1 1 calc R . . H9B H 0.5213 0.1688 0.7167 0.034 Uiso 1 1 calc R . . C10 C 0.4492(4) 0.3554(4) 0.68739(12) 0.0279(10) Uani 1 1 d . . . H10A H 0.4763 0.3882 0.6677 0.034 Uiso 1 1 calc R . . H10B H 0.5065 0.3643 0.7039 0.034 Uiso 1 1 calc R . . C11 C 0.3455(3) 0.4132(4) 0.69746(11) 0.0243(9) Uani 1 1 d . . . H11A H 0.3262 0.3901 0.7190 0.029 Uiso 1 1 calc R . . H11B H 0.3588 0.4921 0.6979 0.029 Uiso 1 1 calc R . . C12 C 0.1007(4) 0.2643(4) 0.54940(10) 0.0284(10) Uani 1 1 d . . . C13 C 0.0006(4) 0.3101(4) 0.54301(11) 0.0329(11) Uani 1 1 d . . . H13 H -0.0286 0.3628 0.5568 0.040 Uiso 1 1 calc R . . C14 C -0.0583(4) 0.2788(4) 0.51597(11) 0.0356(12) Uani 1 1 d . . . H14 H -0.1270 0.3112 0.5113 0.043 Uiso 1 1 calc R . . C15 C -0.0168(4) 0.2013(4) 0.49632(11) 0.0313(11) Uani 1 1 d . . . C16 C 0.0863(4) 0.1536(4) 0.50253(10) 0.0296(10) Uani 1 1 d . . . C17 C 0.1488(4) 0.1861(4) 0.52957(10) 0.0287(10) Uani 1 1 d . . . C18 C 0.2533(4) 0.1387(4) 0.53463(11) 0.0319(11) Uani 1 1 d . . . H18 H 0.2970 0.1610 0.5521 0.038 Uiso 1 1 calc R . . C19 C 0.2917(4) 0.0613(4) 0.51457(11) 0.0353(12) Uani 1 1 d . . . H19 H 0.3616 0.0300 0.5183 0.042 Uiso 1 1 calc R . . C20 C 0.2287(4) 0.0278(4) 0.48854(11) 0.0362(12) Uani 1 1 d . . . H20 H 0.2556 -0.0271 0.4751 0.043 Uiso 1 1 calc R . . C21 C 0.1288(4) 0.0736(4) 0.48232(10) 0.0310(11) Uani 1 1 d . . . C22 C 0.0639(4) 0.0385(4) 0.45447(11) 0.0343(11) Uani 1 1 d . . . C23 C -0.0828(4) 0.1669(4) 0.46838(11) 0.0338(11) Uani 1 1 d . . . C24 C -0.1024(5) 0.0515(5) 0.42126(12) 0.0439(14) Uani 1 1 d . . . H24A H -0.1815 0.0623 0.4249 0.053 Uiso 1 1 calc R . . H24B H -0.0900 -0.0262 0.4172 0.053 Uiso 1 1 calc R . . C25 C -0.0677(5) 0.1168(6) 0.39291(12) 0.0570(18) Uani 1 1 d . . . H25A H -0.0783 0.1938 0.3972 0.085 Uiso 1 1 calc R . . H25B H -0.1121 0.0958 0.3745 0.085 Uiso 1 1 calc R . . H25C H 0.0097 0.1030 0.3887 0.085 Uiso 1 1 calc R . . C26 C -0.1009(4) 0.1771(4) 0.62322(12) 0.0339(11) Uani 1 1 d . . . C27 C -0.1930(5) 0.2220(5) 0.60570(13) 0.0411(13) Uani 1 1 d . . . H27A H -0.1841 0.2073 0.5832 0.062 Uiso 1 1 calc R . . H27B H -0.1960 0.3002 0.6091 0.062 Uiso 1 1 calc R . . H27C H -0.2610 0.1889 0.6130 0.062 Uiso 1 1 calc R . . N1 N 0.2226(3) 0.2649(3) 0.62349(8) 0.0242(8) Uani 1 1 d . . . N2 N 0.1828(3) 0.2154(3) 0.59874(8) 0.0277(8) Uani 1 1 d . . . N3 N 0.1563(3) 0.2939(3) 0.57823(8) 0.0287(9) Uani 1 1 d . . . N4 N 0.2540(3) 0.3893(3) 0.67576(8) 0.0198(7) Uani 1 1 d . . . N5 N 0.1110(3) 0.2167(3) 0.69072(9) 0.0224(8) Uani 1 1 d . . . N6 N 0.2821(3) 0.0683(3) 0.69491(9) 0.0265(8) Uani 1 1 d . . . N7 N 0.4282(3) 0.2390(3) 0.68219(9) 0.0246(8) Uani 1 1 d . . . N8 N -0.0390(4) 0.0853(4) 0.44963(9) 0.0340(10) Uani 1 1 d . . . N9 N -0.0309(4) 0.1391(4) 0.63750(11) 0.0416(11) Uani 1 1 d . . . O1 O -0.1709(3) 0.2076(3) 0.46165(8) 0.0428(9) Uani 1 1 d . . . O2 O 0.0980(3) -0.0295(3) 0.43608(8) 0.0466(10) Uani 1 1 d . . . Zn1 Zn 0.26402(4) 0.20861(4) 0.666821(13) 0.01962(16) Uani 1 1 d . . . Cl1A Cl 0.4461(2) 1.0320(3) 0.61607(5) 0.0303(8) Uani 0.650(10) 1 d PD A 1 O3A O 0.4662(5) 0.9194(4) 0.62148(13) 0.0417(19) Uiso 0.637(11) 1 d PD A 1 O4A O 0.5302(5) 1.0927(5) 0.6313(2) 0.044(3) Uiso 0.79(4) 1 d PD A 1 O5A O 0.4501(6) 1.0543(6) 0.58280(12) 0.052(2) Uiso 0.647(12) 1 d PD A 1 O6A O 0.3410(6) 1.0578(8) 0.6289(2) 0.035(4) Uiso 0.60 1 d PD A 1 Cl1B Cl 0.4360(4) 1.0869(7) 0.60801(17) 0.061(3) Uani 0.350(10) 1 d PD A 2 O3B O 0.4329(11) 1.0084(9) 0.5840(2) 0.059(4) Uiso 0.363(11) 1 d PD A 2 O4B O 0.5360(11) 1.0857(15) 0.6253(4) 0.046(11) Uiso 0.21(4) 1 d PD A 2 O5B O 0.4224(9) 1.1925(7) 0.5942(3) 0.055(4) Uiso 0.353(12) 1 d PD A 2 O6B O 0.3454(12) 1.0690(13) 0.6288(4) 0.063(10) Uiso 0.40 1 d PD A 2 Cl2 Cl -0.24216(8) 0.25876(8) 0.69902(2) 0.0245(2) Uani 1 1 d D . . O7A O -0.3083(5) 0.1839(6) 0.68141(18) 0.038(2) Uiso 0.59(2) 1 d PD B 1 O8A O -0.1461(4) 0.1993(5) 0.71089(12) 0.036(2) Uiso 0.631(17) 1 d PD B 1 O9A O -0.2001(6) 0.3379(5) 0.67757(14) 0.042(2) Uiso 0.578(15) 1 d PD B 1 O10A O -0.2976(7) 0.3076(7) 0.72381(17) 0.037(3) Uiso 0.60 1 d PD B 1 O7B O -0.2908(8) 0.1582(6) 0.6907(3) 0.035(3) Uiso 0.41(2) 1 d PD B 2 O8B O -0.1335(5) 0.2564(11) 0.7072(2) 0.052(4) Uiso 0.369(17) 1 d PD B 2 O9B O -0.2663(8) 0.3371(6) 0.67505(17) 0.041(3) Uiso 0.422(15) 1 d PD B 2 O10B O -0.3043(8) 0.2953(8) 0.72733(19) 0.021(3) Uiso 0.40 1 d PD B 2 H6 H 0.267(5) 0.013(5) 0.6848(13) 0.036(16) Uiso 1 1 d . . . H5 H 0.067(4) 0.227(4) 0.6762(11) 0.013(11) Uiso 1 1 d . . . H7 H 0.466(4) 0.216(4) 0.6679(13) 0.031(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 C1 0.038(3) 0.025(2) 0.024(2) 0.0017(19) 0.001(2) 0.008(2) C2 0.025(2) 0.025(2) 0.023(2) -0.0004(18) 0.0022(18) 0.0065(18) C3 0.029(2) 0.020(2) 0.027(2) 0.0017(18) 0.0015(18) 0.0007(18) C4 0.024(2) 0.024(2) 0.028(2) -0.0015(18) -0.0001(18) 0.0061(18) C5 0.018(2) 0.026(2) 0.028(2) -0.0015(19) -0.0004(17) 0.0018(18) C6 0.028(2) 0.029(3) 0.034(3) 0.003(2) 0.003(2) -0.010(2) C7 0.036(3) 0.019(2) 0.029(2) 0.0036(18) 0.000(2) -0.0027(19) C8 0.031(3) 0.030(3) 0.038(3) 0.000(2) -0.002(2) 0.012(2) C9 0.021(2) 0.031(3) 0.032(2) 0.002(2) -0.0050(19) 0.0041(19) C10 0.020(2) 0.028(2) 0.036(3) 0.000(2) -0.0029(19) -0.0063(19) C11 0.022(2) 0.021(2) 0.030(2) -0.0056(18) -0.0052(18) -0.0028(18) C12 0.034(3) 0.033(3) 0.019(2) -0.0036(19) -0.0004(18) 0.003(2) C13 0.038(3) 0.037(3) 0.024(2) -0.004(2) 0.003(2) 0.010(2) C14 0.037(3) 0.043(3) 0.027(2) -0.002(2) 0.000(2) 0.010(2) C15 0.037(3) 0.037(3) 0.020(2) -0.003(2) 0.0022(19) 0.004(2) C16 0.037(3) 0.034(3) 0.018(2) 0.0003(19) 0.0037(19) 0.004(2) C17 0.034(3) 0.033(3) 0.019(2) -0.0014(19) 0.0027(19) 0.006(2) C18 0.033(3) 0.041(3) 0.022(2) 0.002(2) 0.0008(19) 0.005(2) C19 0.037(3) 0.040(3) 0.029(3) 0.002(2) 0.004(2) 0.012(2) C20 0.046(3) 0.040(3) 0.023(2) -0.002(2) 0.006(2) 0.011(2) C21 0.041(3) 0.036(3) 0.016(2) -0.0021(19) 0.0032(19) 0.005(2) C22 0.047(3) 0.037(3) 0.020(2) -0.003(2) 0.002(2) 0.002(2) C23 0.037(3) 0.043(3) 0.022(2) 0.002(2) 0.003(2) 0.004(2) C24 0.053(3) 0.052(3) 0.027(3) -0.009(2) -0.007(2) 0.006(3) C25 0.054(4) 0.094(5) 0.023(3) 0.004(3) 0.005(2) 0.032(4) C26 0.034(3) 0.038(3) 0.030(3) -0.008(2) 0.002(2) -0.006(2) C27 0.043(3) 0.042(3) 0.038(3) -0.006(2) -0.004(2) 0.003(2) N1 0.031(2) 0.0196(19) 0.0225(19) -0.0019(15) 0.0007(15) 0.0024(15) N2 0.037(2) 0.027(2) 0.0196(19) -0.0032(16) -0.0025(16) 0.0001(17) N3 0.036(2) 0.033(2) 0.0169(18) -0.0017(16) -0.0008(16) 0.0120(18) N4 0.0218(18) 0.0180(18) 0.0196(17) -0.0028(14) -0.0003(14) 0.0021(14) N5 0.0173(18) 0.0229(19) 0.027(2) 0.0011(16) -0.0039(16) -0.0010(15) N6 0.032(2) 0.0169(19) 0.030(2) -0.0031(17) -0.0025(17) 0.0029(16) N7 0.0166(18) 0.030(2) 0.027(2) -0.0024(17) 0.0003(15) 0.0047(16) N8 0.044(2) 0.039(2) 0.0189(19) -0.0027(17) -0.0007(17) 0.003(2) N9 0.034(2) 0.050(3) 0.041(3) -0.008(2) -0.006(2) -0.003(2) O1 0.040(2) 0.059(2) 0.0292(18) -0.0055(17) -0.0036(15) 0.0091(19) O2 0.066(3) 0.048(2) 0.0260(18) -0.0120(17) -0.0027(17) 0.014(2) Zn1 0.0210(3) 0.0182(3) 0.0195(3) -0.0013(2) -0.0017(2) -0.0001(2) Cl1A 0.0339(12) 0.0304(15) 0.0263(11) -0.0076(9) -0.0032(7) 0.0097(9) Cl1B 0.045(3) 0.065(5) 0.071(4) -0.045(4) -0.026(2) 0.024(3) Cl2 0.0271(5) 0.0206(5) 0.0257(5) 0.0002(4) -0.0042(4) -0.0036(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 N3 1.352(6) . ? C1 C2 1.362(6) . ? C1 H1 0.9500 . ? C2 N1 1.367(6) . ? C2 C3 1.497(6) . ? C3 N4 1.487(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N4 1.474(5) . ? C4 C5 1.508(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N5 1.475(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N5 1.465(6) . ? C6 C7 1.517(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N6 1.470(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N6 1.474(6) . ? C8 C9 1.516(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N7 1.479(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N7 1.480(6) . ? C10 C11 1.521(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N4 1.471(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.372(7) . ? C12 C17 1.416(6) . ? C12 N3 1.440(6) . ? C13 C14 1.403(7) . ? C13 H13 0.9500 . ? C14 C15 1.373(7) . ? C14 H14 0.9500 . ? C15 C16 1.413(7) . ? C15 C23 1.489(7) . ? C16 C21 1.414(7) . ? C16 C17 1.429(7) . ? C17 C18 1.419(7) . ? C18 C19 1.369(7) . ? C18 H18 0.9500 . ? C19 C20 1.402(7) . ? C19 H19 0.9500 . ? C20 C21 1.369(7) . ? C20 H20 0.9500 . ? C21 C22 1.481(7) . ? C22 O2 1.226(6) . ? C22 N8 1.397(7) . ? C23 O1 1.220(6) . ? C23 N8 1.396(6) . ? C24 N8 1.485(6) . ? C24 C25 1.515(8) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 N9 1.144(7) . ? C26 C27 1.453(8) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? N1 N2 1.305(5) . ? N1 Zn1 2.026(4) . ? N2 N3 1.342(5) . ? N4 Zn1 2.274(3) . ? N5 Zn1 2.141(4) . ? N5 H5 0.83(5) . ? N6 Zn1 2.118(4) . ? N6 H6 0.82(6) . ? N7 Zn1 2.135(4) . ? N7 H7 0.82(6) . ? Cl1A O4A 1.423(5) . ? Cl1A O3A 1.435(5) . ? Cl1A O6A 1.437(5) . ? Cl1A O5A 1.441(5) . ? Cl1B O3B 1.410(7) . ? Cl1B O4B 1.417(8) . ? Cl1B O6B 1.440(8) . ? Cl1B O5B 1.442(9) . ? Cl2 O8B 1.368(6) . ? Cl2 O10A 1.396(5) . ? Cl2 O7B 1.423(6) . ? Cl2 O9B 1.434(6) . ? Cl2 O9A 1.437(5) . ? Cl2 O7A 1.434(5) . ? Cl2 O8A 1.470(5) . ? Cl2 O10B 1.499(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 N3 C1 C2 104.9(4) . . ? N3 C1 H1 127.5 . . ? C2 C1 H1 127.5 . . ? C1 C2 N1 106.8(4) . . ? C1 C2 C3 133.7(4) . . ? N1 C2 C3 119.5(4) . . ? N4 C3 C2 109.1(4) . . ? N4 C3 H3A 109.9 . . ? C2 C3 H3A 109.9 . . ? N4 C3 H3B 109.9 . . ? C2 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? N4 C4 C5 111.4(4) . . ? N4 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? N4 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? N5 C5 C4 108.4(4) . . ? N5 C5 H5A 110.0 . . ? C4 C5 H5A 110.0 . . ? N5 C5 H5B 110.0 . . ? C4 C5 H5B 110.0 . . ? H5A C5 H5B 108.4 . . ? N5 C6 C7 109.9(4) . . ? N5 C6 H6A 109.7 . . ? C7 C6 H6A 109.7 . . ? N5 C6 H6B 109.7 . . ? C7 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? N6 C7 C6 108.6(4) . . ? N6 C7 H7A 110.0 . . ? C6 C7 H7A 110.0 . . ? N6 C7 H7B 110.0 . . ? C6 C7 H7B 110.0 . . ? H7A C7 H7B 108.3 . . ? N6 C8 C9 109.6(4) . . ? N6 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? N6 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? N7 C9 C8 109.3(4) . . ? N7 C9 H9A 109.8 . . ? C8 C9 H9A 109.8 . . ? N7 C9 H9B 109.8 . . ? C8 C9 H9B 109.8 . . ? H9A C9 H9B 108.3 . . ? N7 C10 C11 110.9(4) . . ? N7 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? N7 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.0 . . ? N4 C11 C10 111.0(4) . . ? N4 C11 H11A 109.4 . . ? C10 C11 H11A 109.4 . . ? N4 C11 H11B 109.4 . . ? C10 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C13 C12 C17 122.7(4) . . ? C13 C12 N3 118.2(4) . . ? C17 C12 N3 119.0(4) . . ? C12 C13 C14 119.7(4) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 120.1(5) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.9(4) . . ? C14 C15 C23 119.0(5) . . ? C16 C15 C23 120.1(4) . . ? C15 C16 C21 120.8(4) . . ? C15 C16 C17 119.9(4) . . ? C21 C16 C17 119.2(4) . . ? C12 C17 C18 124.9(4) . . ? C12 C17 C16 116.7(4) . . ? C18 C17 C16 118.5(4) . . ? C19 C18 C17 120.7(5) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C20 120.6(5) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C21 C20 C19 120.6(5) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C16 120.4(4) . . ? C20 C21 C22 120.0(4) . . ? C16 C21 C22 119.5(4) . . ? O2 C22 N8 120.3(5) . . ? O2 C22 C21 121.8(5) . . ? N8 C22 C21 117.9(4) . . ? O1 C23 N8 120.6(5) . . ? O1 C23 C15 122.4(5) . . ? N8 C23 C15 117.0(4) . . ? N8 C24 C25 110.2(5) . . ? N8 C24 H24A 109.6 . . ? C25 C24 H24A 109.6 . . ? N8 C24 H24B 109.6 . . ? C25 C24 H24B 109.6 . . ? H24A C24 H24B 108.1 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N9 C26 C27 177.5(6) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N2 N1 C2 111.0(4) . . ? N2 N1 Zn1 131.0(3) . . ? C2 N1 Zn1 117.4(3) . . ? N1 N2 N3 105.5(4) . . ? N2 N3 C1 111.8(4) . . ? N2 N3 C12 118.4(4) . . ? C1 N3 C12 129.5(4) . . ? C11 N4 C4 113.1(3) . . ? C11 N4 C3 112.7(3) . . ? C4 N4 C3 110.8(3) . . ? C11 N4 Zn1 105.1(3) . . ? C4 N4 Zn1 106.3(3) . . ? C3 N4 Zn1 108.4(2) . . ? C6 N5 C5 114.7(4) . . ? C6 N5 Zn1 108.6(3) . . ? C5 N5 Zn1 108.0(3) . . ? C6 N5 H5 115(3) . . ? C5 N5 H5 107(3) . . ? Zn1 N5 H5 103(3) . . ? C7 N6 C8 113.4(4) . . ? C7 N6 Zn1 107.7(3) . . ? C8 N6 Zn1 108.0(3) . . ? C7 N6 H6 108(4) . . ? C8 N6 H6 108(4) . . ? Zn1 N6 H6 111(4) . . ? C9 N7 C10 113.2(4) . . ? C9 N7 Zn1 105.0(3) . . ? C10 N7 Zn1 112.2(3) . . ? C9 N7 H7 111(4) . . ? C10 N7 H7 110(4) . . ? Zn1 N7 H7 105(4) . . ? C23 N8 C22 124.5(4) . . ? C23 N8 C24 117.8(4) . . ? C22 N8 C24 117.5(4) . . ? N1 Zn1 N6 144.77(16) . . ? N1 Zn1 N7 116.14(15) . . ? N6 Zn1 N7 83.19(15) . . ? N1 Zn1 N5 101.77(15) . . ? N6 Zn1 N5 81.81(15) . . ? N7 Zn1 N5 132.04(15) . . ? N1 Zn1 N4 78.43(14) . . ? N6 Zn1 N4 136.01(14) . . ? N7 Zn1 N4 80.08(14) . . ? N5 Zn1 N4 79.95(13) . . ? O4A Cl1A O3A 108.6(4) . . ? O4A Cl1A O6A 110.7(5) . . ? O3A Cl1A O6A 107.9(5) . . ? O4A Cl1A O5A 108.1(4) . . ? O3A Cl1A O5A 109.6(4) . . ? O6A Cl1A O5A 111.8(5) . . ? O3B Cl1B O4B 112.5(8) . . ? O3B Cl1B O6B 108.8(7) . . ? O4B Cl1B O6B 110.2(8) . . ? O3B Cl1B O5B 109.2(7) . . ? O4B Cl1B O5B 108.3(7) . . ? O6B Cl1B O5B 107.6(7) . . ? O8B Cl2 O10A 107.3(6) . . ? O8B Cl2 O7B 116.4(6) . . ? O10A Cl2 O7B 111.1(6) . . ? O8B Cl2 O9B 112.6(6) . . ? O10A Cl2 O9B 98.3(5) . . ? O7B Cl2 O9B 109.6(5) . . ? O8B Cl2 O9A 79.7(5) . . ? O10A Cl2 O9A 111.3(4) . . ? O7B Cl2 O9A 126.3(5) . . ? O9B Cl2 O9A 33.0(4) . . ? O8B Cl2 O7A 131.1(6) . . ? O10A Cl2 O7A 113.4(4) . . ? O7B Cl2 O7A 22.2(4) . . ? O9B Cl2 O7A 87.6(5) . . ? O9A Cl2 O7A 108.3(4) . . ? O8B Cl2 O8A 30.0(5) . . ? O10A Cl2 O8A 110.6(4) . . ? O7B Cl2 O8A 88.6(5) . . ? O9B Cl2 O8A 137.7(4) . . ? O9A Cl2 O8A 105.6(4) . . ? O7A Cl2 O8A 107.3(4) . . ? O8B Cl2 O10B 107.6(5) . . ? O10A Cl2 O10B 8.1(6) . . ? O7B Cl2 O10B 104.4(5) . . ? O9B Cl2 O10B 105.2(5) . . ? O9A Cl2 O10B 119.4(5) . . ? O7A Cl2 O10B 109.0(5) . . ? O8A Cl2 O10B 106.6(5) . . ? 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 N3 C1 C2 N1 -0.3(5) . . . . ? N3 C1 C2 C3 179.3(5) . . . . ? C1 C2 C3 N4 154.9(5) . . . . ? N1 C2 C3 N4 -25.5(6) . . . . ? N4 C4 C5 N5 -56.9(5) . . . . ? N5 C6 C7 N6 -54.3(5) . . . . ? N6 C8 C9 N7 -56.3(5) . . . . ? N7 C10 C11 N4 -51.2(5) . . . . ? C17 C12 C13 C14 0.5(8) . . . . ? N3 C12 C13 C14 -176.6(5) . . . . ? C12 C13 C14 C15 1.1(8) . . . . ? C13 C14 C15 C16 -1.3(8) . . . . ? C13 C14 C15 C23 177.9(5) . . . . ? C14 C15 C16 C21 179.8(5) . . . . ? C23 C15 C16 C21 0.5(7) . . . . ? C14 C15 C16 C17 0.0(8) . . . . ? C23 C15 C16 C17 -179.3(5) . . . . ? C13 C12 C17 C18 178.0(5) . . . . ? N3 C12 C17 C18 -4.9(7) . . . . ? C13 C12 C17 C16 -1.8(7) . . . . ? N3 C12 C17 C16 175.3(4) . . . . ? C15 C16 C17 C12 1.6(7) . . . . ? C21 C16 C17 C12 -178.3(4) . . . . ? C15 C16 C17 C18 -178.3(5) . . . . ? C21 C16 C17 C18 1.9(7) . . . . ? C12 C17 C18 C19 178.2(5) . . . . ? C16 C17 C18 C19 -2.0(7) . . . . ? C17 C18 C19 C20 0.4(8) . . . . ? C18 C19 C20 C21 1.4(8) . . . . ? C19 C20 C21 C16 -1.5(8) . . . . ? C19 C20 C21 C22 179.1(5) . . . . ? C15 C16 C21 C20 -180.0(5) . . . . ? C17 C16 C21 C20 -0.1(7) . . . . ? C15 C16 C21 C22 -0.6(7) . . . . ? C17 C16 C21 C22 179.2(5) . . . . ? C20 C21 C22 O2 -1.6(8) . . . . ? C16 C21 C22 O2 179.0(5) . . . . ? C20 C21 C22 N8 178.2(5) . . . . ? C16 C21 C22 N8 -1.2(7) . . . . ? C14 C15 C23 O1 2.6(8) . . . . ? C16 C15 C23 O1 -178.1(5) . . . . ? C14 C15 C23 N8 -178.0(5) . . . . ? C16 C15 C23 N8 1.3(7) . . . . ? C1 C2 N1 N2 -0.2(5) . . . . ? C3 C2 N1 N2 -179.9(4) . . . . ? C1 C2 N1 Zn1 -172.3(3) . . . . ? C3 C2 N1 Zn1 8.0(5) . . . . ? C2 N1 N2 N3 0.6(5) . . . . ? Zn1 N1 N2 N3 171.3(3) . . . . ? N1 N2 N3 C1 -0.8(5) . . . . ? N1 N2 N3 C12 -174.5(4) . . . . ? C2 C1 N3 N2 0.7(5) . . . . ? C2 C1 N3 C12 173.5(4) . . . . ? C13 C12 N3 N2 122.0(5) . . . . ? C17 C12 N3 N2 -55.2(6) . . . . ? C13 C12 N3 C1 -50.4(7) . . . . ? C17 C12 N3 C1 132.3(5) . . . . ? C10 C11 N4 C4 159.3(4) . . . . ? C10 C11 N4 C3 -74.1(5) . . . . ? C10 C11 N4 Zn1 43.8(4) . . . . ? C5 C4 N4 C11 -81.3(4) . . . . ? C5 C4 N4 C3 151.0(4) . . . . ? C5 C4 N4 Zn1 33.4(4) . . . . ? C2 C3 N4 C11 143.9(4) . . . . ? C2 C3 N4 C4 -88.2(4) . . . . ? C2 C3 N4 Zn1 28.0(4) . . . . ? C7 C6 N5 C5 -85.2(5) . . . . ? C7 C6 N5 Zn1 35.6(4) . . . . ? C4 C5 N5 C6 170.6(4) . . . . ? C4 C5 N5 Zn1 49.4(4) . . . . ? C6 C7 N6 C8 163.7(4) . . . . ? C6 C7 N6 Zn1 44.2(4) . . . . ? C9 C8 N6 C7 -83.8(5) . . . . ? C9 C8 N6 Zn1 35.5(4) . . . . ? C8 C9 N7 C10 168.6(4) . . . . ? C8 C9 N7 Zn1 45.9(4) . . . . ? C11 C10 N7 C9 -88.5(4) . . . . ? C11 C10 N7 Zn1 30.1(5) . . . . ? O1 C23 N8 C22 176.1(5) . . . . ? C15 C23 N8 C22 -3.3(7) . . . . ? O1 C23 N8 C24 0.7(7) . . . . ? C15 C23 N8 C24 -178.7(5) . . . . ? O2 C22 N8 C23 -176.9(5) . . . . ? C21 C22 N8 C23 3.3(7) . . . . ? O2 C22 N8 C24 -1.5(7) . . . . ? C21 C22 N8 C24 178.7(5) . . . . ? C25 C24 N8 C23 91.3(6) . . . . ? C25 C24 N8 C22 -84.4(6) . . . . ? N2 N1 Zn1 N6 6.2(5) . . . . ? C2 N1 Zn1 N6 176.5(3) . . . . ? N2 N1 Zn1 N7 124.0(4) . . . . ? C2 N1 Zn1 N7 -65.7(4) . . . . ? N2 N1 Zn1 N5 -86.2(4) . . . . ? C2 N1 Zn1 N5 84.0(3) . . . . ? N2 N1 Zn1 N4 -163.2(4) . . . . ? C2 N1 Zn1 N4 7.0(3) . . . . ? C7 N6 Zn1 N1 -118.4(3) . . . . ? C8 N6 Zn1 N1 118.8(3) . . . . ? C7 N6 Zn1 N7 114.7(3) . . . . ? C8 N6 Zn1 N7 -8.1(3) . . . . ? C7 N6 Zn1 N5 -19.6(3) . . . . ? C8 N6 Zn1 N5 -142.4(3) . . . . ? C7 N6 Zn1 N4 46.7(4) . . . . ? C8 N6 Zn1 N4 -76.2(4) . . . . ? C9 N7 Zn1 N1 -169.7(3) . . . . ? C10 N7 Zn1 N1 67.0(3) . . . . ? C9 N7 Zn1 N6 -20.6(3) . . . . ? C10 N7 Zn1 N6 -144.0(3) . . . . ? C9 N7 Zn1 N5 51.9(4) . . . . ? C10 N7 Zn1 N5 -71.5(4) . . . . ? C9 N7 Zn1 N4 118.5(3) . . . . ? C10 N7 Zn1 N4 -4.8(3) . . . . ? C6 N5 Zn1 N1 135.4(3) . . . . ? C5 N5 Zn1 N1 -99.7(3) . . . . ? C6 N5 Zn1 N6 -8.9(3) . . . . ? C5 N5 Zn1 N6 115.9(3) . . . . ? C6 N5 Zn1 N7 -82.0(3) . . . . ? C5 N5 Zn1 N7 42.8(4) . . . . ? C6 N5 Zn1 N4 -148.7(3) . . . . ? C5 N5 Zn1 N4 -23.9(3) . . . . ? C11 N4 Zn1 N1 -140.7(3) . . . . ? C4 N4 Zn1 N1 99.2(3) . . . . ? C3 N4 Zn1 N1 -19.9(3) . . . . ? C11 N4 Zn1 N6 48.0(3) . . . . ? C4 N4 Zn1 N6 -72.1(3) . . . . ? C3 N4 Zn1 N6 168.8(3) . . . . ? C11 N4 Zn1 N7 -21.2(3) . . . . ? C4 N4 Zn1 N7 -141.3(3) . . . . ? C3 N4 Zn1 N7 99.6(3) . . . . ? C11 N4 Zn1 N5 115.0(3) . . . . ? C4 N4 Zn1 N5 -5.1(3) . . . . ? C3 N4 Zn1 N5 -124.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N6 H6 O9A 0.82(6) 2.23(6) 2.956(7) 146(5) 3_545 N6 H6 O9B 0.82(6) 2.26(6) 3.041(9) 159(5) 3_545 N5 H5 N9 0.83(5) 2.29(5) 2.990(6) 143(4) . N7 H7 O4A 0.82(6) 2.32(6) 3.094(10) 157(5) 1_545 N7 H7 O5B 0.82(6) 3.18(6) 3.779(12) 132(5) 1_545 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 67.27 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 1.035 _refine_diff_density_min -0.733 _refine_diff_density_rms 0.093