# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_111201b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H24 N10' _chemical_formula_weight 548.61 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.3083(18) _cell_length_b 6.8191(5) _cell_length_c 22.558(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.5190(10) _cell_angle_gamma 90.00 _cell_volume 2759.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3863 _cell_measurement_theta_min 3.127 _cell_measurement_theta_max 26.054 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9744 _exptl_absorpt_correction_T_max 0.9834 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13853 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4854 _reflns_number_gt 3235 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material '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^ > 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^)+(0.0461P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4854 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1061 _refine_ls_wR_factor_gt 0.0952 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.25322(7) 0.5360(2) 0.19188(6) 0.0493(4) Uani 1 1 d . . . N2 N 0.20811(7) -0.0549(2) 0.35747(6) 0.0477(4) Uani 1 1 d . . . N3 N 0.36938(7) 0.6090(2) 0.24980(6) 0.0431(4) Uani 1 1 d . . . N4 N 0.48158(7) 0.6559(2) 0.31560(6) 0.0443(4) Uani 1 1 d . . . N5 N 0.55585(7) 0.6943(2) 0.32871(7) 0.0565(4) Uani 1 1 d . . . N6 N 0.20063(7) 0.7783(2) 0.12327(6) 0.0460(4) Uani 1 1 d . . . N7 N 0.15835(7) 1.0245(2) 0.05435(6) 0.0481(4) Uani 1 1 d . . . N8 N 0.10777(9) 1.1046(3) 0.00867(7) 0.0682(5) Uani 1 1 d . . . N9 N 0.39266(11) -0.2050(4) 0.49562(7) 0.0864(7) Uani 1 1 d . . . N10 N -0.00390(9) -0.3328(3) 0.32349(9) 0.0684(5) Uani 1 1 d . . . C1 C 0.24271(8) 0.3865(3) 0.23463(7) 0.0427(4) Uani 1 1 d . . . C2 C 0.28131(9) 0.2115(3) 0.23758(7) 0.0482(5) Uani 1 1 d . . . H2 H 0.3151 0.1912 0.2124 0.058 Uiso 1 1 calc R . . C3 C 0.27007(9) 0.0662(3) 0.27762(7) 0.0484(5) Uani 1 1 d . . . H3 H 0.2957 -0.0521 0.2790 0.058 Uiso 1 1 calc R . . C4 C 0.22050(8) 0.0977(3) 0.31574(7) 0.0423(4) Uani 1 1 d . . . C5 C 0.18266(9) 0.2726(3) 0.31357(7) 0.0486(5) Uani 1 1 d . . . H5 H 0.1496 0.2938 0.3393 0.058 Uiso 1 1 calc R . . C6 C 0.19362(9) 0.4175(3) 0.27311(7) 0.0498(5) Uani 1 1 d . . . H6 H 0.1680 0.5356 0.2718 0.060 Uiso 1 1 calc R . . C7 C 0.32754(8) 0.6016(2) 0.19383(7) 0.0419(4) Uani 1 1 d . . . C8 C 0.35569(9) 0.6445(3) 0.14252(7) 0.0478(4) Uani 1 1 d . . . H8 H 0.3250 0.6430 0.1043 0.057 Uiso 1 1 calc R . . C9 C 0.43036(9) 0.6893(3) 0.14986(8) 0.0505(5) Uani 1 1 d . . . H9 H 0.4506 0.7179 0.1162 0.061 Uiso 1 1 calc R . . C10 C 0.47553(9) 0.6919(3) 0.20711(7) 0.0474(5) Uani 1 1 d . . . H10 H 0.5262 0.7190 0.2129 0.057 Uiso 1 1 calc R . . C11 C 0.44141(8) 0.6525(2) 0.25481(7) 0.0399(4) Uani 1 1 d . . . C12 C 0.57276(10) 0.6866(3) 0.38889(9) 0.0623(5) Uani 1 1 d . . . H12 H 0.6204 0.7087 0.4114 0.075 Uiso 1 1 calc R . . C13 C 0.51217(10) 0.6425(3) 0.41424(8) 0.0658(6) Uani 1 1 d . . . H13 H 0.5111 0.6284 0.4551 0.079 Uiso 1 1 calc R . . C14 C 0.45407(10) 0.6243(3) 0.36622(8) 0.0602(5) Uani 1 1 d . . . H14 H 0.4049 0.5956 0.3679 0.072 Uiso 1 1 calc R . . C15 C 0.19128(8) 0.6065(3) 0.14985(7) 0.0451(4) Uani 1 1 d . . . C16 C 0.12440(9) 0.5020(3) 0.13686(8) 0.0555(5) Uani 1 1 d . . . H16 H 0.1191 0.3831 0.1558 0.067 Uiso 1 1 calc R . . C17 C 0.06646(9) 0.5810(3) 0.09504(9) 0.0630(6) Uani 1 1 d . . . H17 H 0.0211 0.5151 0.0860 0.076 Uiso 1 1 calc R . . C18 C 0.07475(9) 0.7564(3) 0.06648(8) 0.0566(5) Uani 1 1 d . . . H18 H 0.0361 0.8111 0.0382 0.068 Uiso 1 1 calc R . . C19 C 0.14301(9) 0.8453(3) 0.08207(7) 0.0451(4) Uani 1 1 d . . . C20 C 0.14251(12) 1.2599(3) -0.00748(9) 0.0691(6) Uani 1 1 d . . . H20 H 0.1214 1.3442 -0.0386 0.083 Uiso 1 1 calc R . . C21 C 0.21323(12) 1.2835(3) 0.02677(9) 0.0706(6) Uani 1 1 d . . . H21 H 0.2474 1.3821 0.0238 0.085 Uiso 1 1 calc R . . C22 C 0.22176(10) 1.1296(3) 0.06601(9) 0.0661(6) Uani 1 1 d . . . H22 H 0.2638 1.1021 0.0955 0.079 Uiso 1 1 calc R . . C23 C 0.38524(12) -0.0302(4) 0.46876(10) 0.0784(7) Uani 1 1 d . . . H23 H 0.4227 0.0616 0.4813 0.094 Uiso 1 1 calc R . . C24 C 0.32600(10) 0.0252(3) 0.42369(8) 0.0628(6) Uani 1 1 d . . . H24 H 0.3243 0.1501 0.4069 0.075 Uiso 1 1 calc R . . C25 C 0.26886(9) -0.1090(3) 0.40366(7) 0.0480(5) Uani 1 1 d . . . C26 C 0.27719(10) -0.2938(3) 0.43000(8) 0.0616(5) Uani 1 1 d . . . H26 H 0.2420 -0.3912 0.4173 0.074 Uiso 1 1 calc R . . C27 C 0.33845(13) -0.3312(4) 0.47525(9) 0.0808(7) Uani 1 1 d . . . H27 H 0.3419 -0.4550 0.4928 0.097 Uiso 1 1 calc R . . C28 C 0.02268(10) -0.2326(3) 0.28157(9) 0.0615(5) Uani 1 1 d . . . H28 H -0.0072 -0.2253 0.2431 0.074 Uiso 1 1 calc R . . C29 C 0.09079(9) -0.1389(3) 0.29044(8) 0.0510(5) Uani 1 1 d . . . H29 H 0.1054 -0.0717 0.2589 0.061 Uiso 1 1 calc R . . C30 C 0.13748(9) -0.1464(3) 0.34753(7) 0.0436(4) Uani 1 1 d . . . C31 C 0.10950(9) -0.2434(3) 0.39266(8) 0.0518(5) Uani 1 1 d . . . H31 H 0.1369 -0.2474 0.4321 0.062 Uiso 1 1 calc R . . C32 C 0.04080(10) -0.3333(3) 0.37828(9) 0.0622(5) Uani 1 1 d . . . H32 H 0.0242 -0.3995 0.4091 0.075 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0334(7) 0.0598(11) 0.0526(9) 0.0167(7) 0.0039(7) -0.0012(7) N2 0.0400(8) 0.0540(10) 0.0479(8) 0.0126(7) 0.0060(7) -0.0002(7) N3 0.0359(7) 0.0489(10) 0.0441(8) 0.0042(6) 0.0073(6) 0.0017(6) N4 0.0338(7) 0.0508(10) 0.0477(8) 0.0001(7) 0.0068(6) -0.0020(7) N5 0.0398(8) 0.0638(12) 0.0626(10) 0.0005(8) 0.0021(7) -0.0072(7) N6 0.0390(8) 0.0490(10) 0.0479(8) 0.0066(7) 0.0035(7) 0.0017(7) N7 0.0414(8) 0.0531(10) 0.0471(8) 0.0069(7) 0.0022(7) 0.0021(7) N8 0.0616(10) 0.0642(13) 0.0687(11) 0.0193(9) -0.0112(9) 0.0013(9) N9 0.0673(12) 0.147(2) 0.0425(10) 0.0092(12) 0.0055(9) 0.0230(14) N10 0.0529(10) 0.0643(13) 0.0872(13) -0.0010(10) 0.0119(10) -0.0071(9) C1 0.0343(9) 0.0509(12) 0.0422(9) 0.0052(8) 0.0061(7) -0.0020(8) C2 0.0402(9) 0.0603(13) 0.0475(10) 0.0047(9) 0.0169(8) 0.0070(9) C3 0.0446(10) 0.0492(12) 0.0532(11) 0.0049(9) 0.0143(8) 0.0106(9) C4 0.0382(9) 0.0459(12) 0.0422(9) 0.0056(8) 0.0068(7) -0.0005(8) C5 0.0464(10) 0.0552(13) 0.0479(10) 0.0026(9) 0.0183(8) 0.0076(9) C6 0.0494(10) 0.0451(12) 0.0569(11) 0.0036(9) 0.0150(9) 0.0088(9) C7 0.0352(9) 0.0428(11) 0.0473(10) 0.0056(8) 0.0073(8) 0.0023(8) C8 0.0451(10) 0.0552(12) 0.0425(10) 0.0046(8) 0.0074(8) 0.0014(9) C9 0.0506(11) 0.0535(13) 0.0512(11) 0.0074(9) 0.0192(9) -0.0028(9) C10 0.0390(9) 0.0518(13) 0.0525(11) 0.0043(8) 0.0117(8) -0.0061(8) C11 0.0351(9) 0.0392(11) 0.0454(10) 0.0016(7) 0.0076(7) 0.0002(7) C12 0.0472(11) 0.0737(16) 0.0596(13) -0.0007(10) -0.0048(10) -0.0006(10) C13 0.0553(12) 0.0922(18) 0.0476(11) -0.0004(10) 0.0049(10) 0.0058(11) C14 0.0416(10) 0.0895(16) 0.0515(11) 0.0025(10) 0.0139(9) 0.0028(10) C15 0.0364(9) 0.0513(12) 0.0467(10) 0.0038(8) 0.0062(8) 0.0011(8) C16 0.0427(10) 0.0583(13) 0.0629(12) 0.0121(9) 0.0040(9) -0.0051(9) C17 0.0368(10) 0.0695(15) 0.0771(13) 0.0126(11) -0.0019(10) -0.0083(9) C18 0.0386(10) 0.0631(14) 0.0628(12) 0.0107(10) -0.0024(9) 0.0006(9) C19 0.0394(9) 0.0481(12) 0.0463(10) 0.0036(8) 0.0048(8) 0.0038(8) C20 0.0752(14) 0.0641(16) 0.0631(13) 0.0198(11) 0.0016(11) 0.0003(12) C21 0.0666(13) 0.0745(17) 0.0701(14) 0.0163(11) 0.0120(11) -0.0129(12) C22 0.0492(11) 0.0815(16) 0.0636(12) 0.0182(11) 0.0016(9) -0.0111(11) C23 0.0581(13) 0.115(2) 0.0566(13) -0.0198(14) -0.0016(11) 0.0016(14) C24 0.0553(12) 0.0765(16) 0.0533(11) -0.0061(10) 0.0031(10) 0.0025(11) C25 0.0420(10) 0.0658(14) 0.0374(9) 0.0025(9) 0.0107(8) 0.0062(9) C26 0.0532(11) 0.0775(16) 0.0550(11) 0.0213(10) 0.0127(9) 0.0103(11) C27 0.0679(14) 0.117(2) 0.0598(14) 0.0339(13) 0.0174(12) 0.0252(15) C28 0.0511(11) 0.0595(14) 0.0690(13) -0.0014(10) 0.0004(10) 0.0023(10) C29 0.0482(10) 0.0496(12) 0.0537(11) 0.0029(9) 0.0069(9) 0.0050(9) C30 0.0388(9) 0.0410(11) 0.0518(10) 0.0014(8) 0.0109(8) 0.0048(8) C31 0.0471(10) 0.0553(13) 0.0552(11) 0.0039(9) 0.0152(9) 0.0012(9) C32 0.0548(12) 0.0601(15) 0.0758(14) 0.0048(10) 0.0229(11) -0.0014(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C15 1.4095(19) . ? N1 C7 1.4246(19) . ? N1 C1 1.442(2) . ? N2 C25 1.4127(19) . ? N2 C30 1.413(2) . ? N2 C4 1.451(2) . ? N3 C11 1.3342(19) . ? N3 C7 1.3405(19) . ? N4 C14 1.354(2) . ? N4 N5 1.3581(17) . ? N4 C11 1.4210(19) . ? N5 C12 1.332(2) . ? N6 C19 1.3393(19) . ? N6 C15 1.343(2) . ? N7 C22 1.345(2) . ? N7 N8 1.3552(18) . ? N7 C19 1.426(2) . ? N8 C20 1.323(2) . ? N9 C27 1.325(3) . ? N9 C23 1.332(3) . ? N10 C28 1.335(2) . ? N10 C32 1.339(2) . ? C1 C2 1.382(2) . ? C1 C6 1.385(2) . ? C2 C3 1.384(2) . ? C2 H2 0.9300 . ? C3 C4 1.386(2) . ? C3 H3 0.9300 . ? C4 C5 1.376(2) . ? C5 C6 1.386(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.389(2) . ? C8 C9 1.378(2) . ? C8 H8 0.9300 . ? C9 C10 1.388(2) . ? C9 H9 0.9300 . ? C10 C11 1.374(2) . ? C10 H10 0.9300 . ? C12 C13 1.379(3) . ? C12 H12 0.9300 . ? C13 C14 1.364(2) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.396(2) . ? C16 C17 1.381(2) . ? C16 H16 0.9300 . ? C17 C18 1.381(3) . ? C17 H17 0.9300 . ? C18 C19 1.370(2) . ? C18 H18 0.9300 . ? C20 C21 1.378(3) . ? C20 H20 0.9300 . ? C21 C22 1.362(3) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.383(3) . ? C23 H23 0.9300 . ? C24 C25 1.395(2) . ? C24 H24 0.9300 . ? C25 C26 1.389(3) . ? C26 C27 1.381(3) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 C29 1.380(2) . ? C28 H28 0.9300 . ? C29 C30 1.397(2) . ? C29 H29 0.9300 . ? C30 C31 1.394(2) . ? C31 C32 1.378(2) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? 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 C15 N1 C7 123.29(14) . . ? C15 N1 C1 119.60(13) . . ? C7 N1 C1 117.09(12) . . ? C25 N2 C30 124.23(14) . . ? C25 N2 C4 117.62(13) . . ? C30 N2 C4 118.07(13) . . ? C11 N3 C7 117.22(14) . . ? C14 N4 N5 111.84(13) . . ? C14 N4 C11 127.10(13) . . ? N5 N4 C11 121.07(13) . . ? C12 N5 N4 103.48(15) . . ? C19 N6 C15 117.03(14) . . ? C22 N7 N8 111.48(15) . . ? C22 N7 C19 127.50(14) . . ? N8 N7 C19 120.95(14) . . ? C20 N8 N7 103.81(15) . . ? C27 N9 C23 114.98(19) . . ? C28 N10 C32 114.38(16) . . ? C2 C1 C6 119.41(15) . . ? C2 C1 N1 120.48(15) . . ? C6 C1 N1 120.10(16) . . ? C1 C2 C3 120.58(15) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C2 C3 C4 119.68(16) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 120.00(15) . . ? C5 C4 N2 120.14(14) . . ? C3 C4 N2 119.86(15) . . ? C4 C5 C6 120.21(16) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 120.11(16) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? N3 C7 C8 122.66(14) . . ? N3 C7 N1 113.80(14) . . ? C8 C7 N1 123.46(14) . . ? C9 C8 C7 118.08(15) . . ? C9 C8 H8 121.0 . . ? C7 C8 H8 121.0 . . ? C8 C9 C10 120.48(16) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 116.52(15) . . ? C11 C10 H10 121.7 . . ? C9 C10 H10 121.7 . . ? N3 C11 C10 124.98(15) . . ? N3 C11 N4 113.43(14) . . ? C10 C11 N4 121.59(14) . . ? N5 C12 C13 112.88(16) . . ? N5 C12 H12 123.6 . . ? C13 C12 H12 123.6 . . ? C14 C13 C12 104.76(17) . . ? C14 C13 H13 127.6 . . ? C12 C13 H13 127.6 . . ? N4 C14 C13 107.03(15) . . ? N4 C14 H14 126.5 . . ? C13 C14 H14 126.5 . . ? N6 C15 C16 122.44(15) . . ? N6 C15 N1 116.16(14) . . ? C16 C15 N1 121.41(16) . . ? C17 C16 C15 117.78(17) . . ? C17 C16 H16 121.1 . . ? C15 C16 H16 121.1 . . ? C16 C17 C18 121.05(17) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? C19 C18 C17 116.29(16) . . ? C19 C18 H18 121.9 . . ? C17 C18 H18 121.9 . . ? N6 C19 C18 125.37(17) . . ? N6 C19 N7 113.56(14) . . ? C18 C19 N7 121.07(15) . . ? N8 C20 C21 112.86(17) . . ? N8 C20 H20 123.6 . . ? C21 C20 H20 123.6 . . ? C22 C21 C20 104.33(19) . . ? C22 C21 H21 127.8 . . ? C20 C21 H21 127.8 . . ? N7 C22 C21 107.52(17) . . ? N7 C22 H22 126.2 . . ? C21 C22 H22 126.2 . . ? N9 C23 C24 124.9(2) . . ? N9 C23 H23 117.5 . . ? C24 C23 H23 117.5 . . ? C23 C24 C25 119.1(2) . . ? C23 C24 H24 120.4 . . ? C25 C24 H24 120.4 . . ? C26 C25 C24 116.43(17) . . ? C26 C25 N2 123.75(17) . . ? C24 C25 N2 119.78(17) . . ? C27 C26 C25 119.2(2) . . ? C27 C26 H26 120.4 . . ? C25 C26 H26 120.4 . . ? N9 C27 C26 125.3(2) . . ? N9 C27 H27 117.3 . . ? C26 C27 H27 117.3 . . ? N10 C28 C29 125.53(18) . . ? N10 C28 H28 117.2 . . ? C29 C28 H28 117.2 . . ? C28 C29 C30 119.05(18) . . ? C28 C29 H29 120.5 . . ? C30 C29 H29 120.5 . . ? C31 C30 C29 116.36(15) . . ? C31 C30 N2 123.48(15) . . ? C29 C30 N2 120.15(15) . . ? C32 C31 C30 119.34(17) . . ? C32 C31 H31 120.3 . . ? C30 C31 H31 120.3 . . ? N10 C32 C31 125.24(19) . . ? N10 C32 H32 117.4 . . ? C31 C32 H32 117.4 . . ? 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 C14 N4 N5 C12 -0.4(2) . . . . ? C11 N4 N5 C12 179.36(15) . . . . ? C22 N7 N8 C20 0.6(2) . . . . ? C19 N7 N8 C20 -176.51(16) . . . . ? C15 N1 C1 C2 123.30(17) . . . . ? C7 N1 C1 C2 -55.3(2) . . . . ? C15 N1 C1 C6 -56.6(2) . . . . ? C7 N1 C1 C6 124.82(16) . . . . ? C6 C1 C2 C3 1.4(2) . . . . ? N1 C1 C2 C3 -178.54(15) . . . . ? C1 C2 C3 C4 -1.0(3) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? C2 C3 C4 N2 179.52(15) . . . . ? C25 N2 C4 C5 -116.06(17) . . . . ? C30 N2 C4 C5 67.1(2) . . . . ? C25 N2 C4 C3 64.5(2) . . . . ? C30 N2 C4 C3 -112.33(17) . . . . ? C3 C4 C5 C6 0.3(2) . . . . ? N2 C4 C5 C6 -179.06(15) . . . . ? C2 C1 C6 C5 -0.9(2) . . . . ? N1 C1 C6 C5 179.01(15) . . . . ? C4 C5 C6 C1 0.1(2) . . . . ? C11 N3 C7 C8 -2.5(2) . . . . ? C11 N3 C7 N1 174.27(14) . . . . ? C15 N1 C7 N3 145.58(16) . . . . ? C1 N1 C7 N3 -35.9(2) . . . . ? C15 N1 C7 C8 -37.6(3) . . . . ? C1 N1 C7 C8 140.87(17) . . . . ? N3 C7 C8 C9 2.4(3) . . . . ? N1 C7 C8 C9 -174.11(16) . . . . ? C7 C8 C9 C10 -0.3(3) . . . . ? C8 C9 C10 C11 -1.4(3) . . . . ? C7 N3 C11 C10 0.6(2) . . . . ? C7 N3 C11 N4 -179.61(13) . . . . ? C9 C10 C11 N3 1.3(3) . . . . ? C9 C10 C11 N4 -178.42(15) . . . . ? C14 N4 C11 N3 -1.4(2) . . . . ? N5 N4 C11 N3 178.85(14) . . . . ? C14 N4 C11 C10 178.35(18) . . . . ? N5 N4 C11 C10 -1.4(2) . . . . ? N4 N5 C12 C13 0.7(2) . . . . ? N5 C12 C13 C14 -0.7(2) . . . . ? N5 N4 C14 C13 0.0(2) . . . . ? C11 N4 C14 C13 -179.77(17) . . . . ? C12 C13 C14 N4 0.4(2) . . . . ? C19 N6 C15 C16 -1.5(2) . . . . ? C19 N6 C15 N1 178.37(14) . . . . ? C7 N1 C15 N6 -19.2(2) . . . . ? C1 N1 C15 N6 162.29(15) . . . . ? C7 N1 C15 C16 160.60(16) . . . . ? C1 N1 C15 C16 -17.9(2) . . . . ? N6 C15 C16 C17 0.0(3) . . . . ? N1 C15 C16 C17 -179.86(16) . . . . ? C15 C16 C17 C18 0.8(3) . . . . ? C16 C17 C18 C19 0.0(3) . . . . ? C15 N6 C19 C18 2.4(3) . . . . ? C15 N6 C19 N7 -177.76(14) . . . . ? C17 C18 C19 N6 -1.7(3) . . . . ? C17 C18 C19 N7 178.49(17) . . . . ? C22 N7 C19 N6 -1.4(3) . . . . ? N8 N7 C19 N6 175.28(15) . . . . ? C22 N7 C19 C18 178.48(18) . . . . ? N8 N7 C19 C18 -4.9(3) . . . . ? N7 N8 C20 C21 -0.8(2) . . . . ? N8 C20 C21 C22 0.6(3) . . . . ? N8 N7 C22 C21 -0.3(2) . . . . ? C19 N7 C22 C21 176.64(18) . . . . ? C20 C21 C22 N7 -0.2(2) . . . . ? C27 N9 C23 C24 1.3(3) . . . . ? N9 C23 C24 C25 -0.2(3) . . . . ? C23 C24 C25 C26 -1.8(3) . . . . ? C23 C24 C25 N2 -179.75(16) . . . . ? C30 N2 C25 C26 24.3(3) . . . . ? C4 N2 C25 C26 -152.37(17) . . . . ? C30 N2 C25 C24 -157.93(16) . . . . ? C4 N2 C25 C24 25.4(2) . . . . ? C24 C25 C26 C27 2.7(3) . . . . ? N2 C25 C26 C27 -179.48(16) . . . . ? C23 N9 C27 C26 -0.3(3) . . . . ? C25 C26 C27 N9 -1.7(3) . . . . ? C32 N10 C28 C29 1.8(3) . . . . ? N10 C28 C29 C30 0.1(3) . . . . ? C28 C29 C30 C31 -2.7(2) . . . . ? C28 C29 C30 N2 178.77(16) . . . . ? C25 N2 C30 C31 25.5(3) . . . . ? C4 N2 C30 C31 -157.91(16) . . . . ? C25 N2 C30 C29 -156.08(16) . . . . ? C4 N2 C30 C29 20.6(2) . . . . ? C29 C30 C31 C32 3.3(3) . . . . ? N2 C30 C31 C32 -178.14(17) . . . . ? C28 N10 C32 C31 -1.0(3) . . . . ? C30 C31 C32 N10 -1.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.135 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 968017' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_120303i _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H24 Cl2 N10 Zn' _chemical_formula_weight 684.88 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 19.6653(18) _cell_length_b 11.3358(11) _cell_length_c 14.1097(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3145.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2353 _cell_measurement_theta_min 2.532 _cell_measurement_theta_max 25.896 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 0.991 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8189 _exptl_absorpt_correction_T_max 0.8903 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14473 _diffrn_reflns_av_R_equivalents 0.1117 _diffrn_reflns_av_sigmaI/netI 0.1299 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4768 _reflns_number_gt 2466 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.0319P)^2^+12.6529P] 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 constr _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 0.02(4) _refine_ls_number_reflns 4768 _refine_ls_number_parameters 406 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1508 _refine_ls_R_factor_gt 0.0639 _refine_ls_wR_factor_ref 0.1952 _refine_ls_wR_factor_gt 0.1382 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 0.86766(6) 0.80805(11) 0.36820(12) 0.0499(4) Uani 1 1 d . . . Cl1 Cl 0.90873(16) 0.6272(3) 0.3579(3) 0.0720(9) Uani 1 1 d . . . Cl2 Cl 0.85698(16) 0.9052(3) 0.5061(2) 0.0629(9) Uani 1 1 d . . . N1 N 0.4225(5) 0.4331(8) 0.0631(8) 0.057(3) Uani 1 1 d . . . N2 N 0.5687(4) 0.8122(9) 0.2205(7) 0.043(2) Uani 1 1 d . . . N3 N 0.3334(5) 0.5318(9) 0.1335(8) 0.057(3) Uani 1 1 d . . . N4 N 0.2504(6) 0.6399(11) 0.2130(11) 0.075(4) Uani 1 1 d . . . N5 N 0.1881(8) 0.6900(16) 0.2225(15) 0.117(6) Uani 1 1 d . . . N6 N 0.4036(5) 0.2300(8) 0.0550(7) 0.049(2) Uani 1 1 d . . . N7 N 0.3791(5) 0.0313(7) 0.0502(7) 0.052(3) Uani 1 1 d . . . N8 N 0.3957(6) -0.0804(9) 0.0282(8) 0.069(3) Uani 1 1 d . . . N9 N 0.7723(5) 0.8119(8) 0.3153(6) 0.046(2) Uani 1 1 d . . . N10 N 0.9282(5) 0.9188(9) 0.2924(7) 0.054(3) Uani 1 1 d . . . C1 C 0.4689(6) 0.5226(10) 0.0985(10) 0.048(3) Uani 1 1 d . . . C2 C 0.4729(6) 0.6270(10) 0.0505(8) 0.051(3) Uani 1 1 d . . . H2 H 0.4512 0.6351 -0.0077 0.061 Uiso 1 1 calc R . . C3 C 0.5090(6) 0.7207(10) 0.0880(8) 0.047(3) Uani 1 1 d . . . H3 H 0.5124 0.7913 0.0547 0.057 Uiso 1 1 calc R . . C4 C 0.5400(6) 0.7087(10) 0.1750(9) 0.040(3) Uani 1 1 d . . . C5 C 0.5388(6) 0.6012(11) 0.2212(9) 0.053(3) Uani 1 1 d . . . H5 H 0.5621 0.5916 0.2780 0.064 Uiso 1 1 calc R . . C6 C 0.5027(8) 0.5081(11) 0.1827(10) 0.064(4) Uani 1 1 d . . . H6 H 0.5014 0.4358 0.2138 0.077 Uiso 1 1 calc R . . C7 C 0.3524(6) 0.4579(10) 0.0643(11) 0.060(3) Uani 1 1 d . . . C8 C 0.3081(8) 0.4157(12) -0.0048(12) 0.080(5) Uani 1 1 d . . . H8 H 0.3229 0.3642 -0.0518 0.096 Uiso 1 1 calc R . . C9 C 0.2415(9) 0.4533(13) -0.0008(16) 0.095(6) Uani 1 1 d . . . H9 H 0.2109 0.4278 -0.0467 0.114 Uiso 1 1 calc R . . C10 C 0.2185(8) 0.5296(15) 0.0716(16) 0.088(6) Uani 1 1 d . . . H10 H 0.1737 0.5556 0.0756 0.106 Uiso 1 1 calc R . . C11 C 0.2670(8) 0.5621(12) 0.1349(12) 0.067(4) Uani 1 1 d . . . C12 C 0.1915(14) 0.749(2) 0.302(2) 0.148(11) Uani 1 1 d . . . H12 H 0.1557 0.7946 0.3248 0.178 Uiso 1 1 calc R . . C13 C 0.2535(13) 0.7389(16) 0.3490(19) 0.132(9) Uani 1 1 d . . . H13 H 0.2672 0.7720 0.4062 0.158 Uiso 1 1 calc R . . C14 C 0.2900(10) 0.6650(15) 0.2871(14) 0.096(6) Uani 1 1 d . . . H14 H 0.3342 0.6381 0.2963 0.115 Uiso 1 1 calc R . . C15 C 0.4482(7) 0.3199(11) 0.0455(11) 0.055(4) Uani 1 1 d . . . C16 C 0.5154(7) 0.3029(12) 0.0181(10) 0.071(4) Uani 1 1 d . . . H16 H 0.5450 0.3662 0.0111 0.085 Uiso 1 1 calc R . . C17 C 0.5363(7) 0.1900(12) 0.0018(11) 0.078(5) Uani 1 1 d . . . H17 H 0.5808 0.1765 -0.0174 0.093 Uiso 1 1 calc R . . C18 C 0.4935(7) 0.0966(13) 0.0129(10) 0.062(4) Uani 1 1 d . . . H18 H 0.5083 0.0192 0.0059 0.075 Uiso 1 1 calc R . . C19 C 0.4269(6) 0.1231(10) 0.0351(8) 0.049(3) Uani 1 1 d . . . C20 C 0.3402(7) -0.1431(12) 0.0528(11) 0.071(4) Uani 1 1 d . . . H20 H 0.3367 -0.2245 0.0463 0.086 Uiso 1 1 calc R . . C21 C 0.2883(7) -0.0711(12) 0.0893(10) 0.065(4) Uani 1 1 d . . . H21 H 0.2459 -0.0938 0.1118 0.078 Uiso 1 1 calc R . . C22 C 0.3144(7) 0.0388(12) 0.0841(10) 0.065(4) Uani 1 1 d . . . H22 H 0.2919 0.1080 0.1008 0.078 Uiso 1 1 calc R . . C23 C 0.7258(5) 0.8864(9) 0.3494(8) 0.048(3) Uani 1 1 d . . . H23 H 0.7399 0.9402 0.3951 0.058 Uiso 1 1 calc R . . C24 C 0.6592(5) 0.8896(11) 0.3221(8) 0.050(3) Uani 1 1 d . . . H24 H 0.6292 0.9413 0.3517 0.060 Uiso 1 1 calc R . . C25 C 0.6354(5) 0.8136(10) 0.2481(7) 0.038(2) Uani 1 1 d . . . C26 C 0.6838(6) 0.7377(10) 0.2128(8) 0.046(3) Uani 1 1 d . . . H26 H 0.6714 0.6851 0.1653 0.055 Uiso 1 1 calc R . . C27 C 0.7497(5) 0.7367(9) 0.2450(9) 0.046(3) Uani 1 1 d . . . H27 H 0.7802 0.6834 0.2185 0.055 Uiso 1 1 calc R . . C28 C 0.9103(6) 1.0359(11) 0.2891(9) 0.056(3) Uani 1 1 d . . . H28 H 0.8664 1.0569 0.3068 0.067 Uiso 1 1 calc R . . C29 C 0.9547(6) 1.1243(10) 0.2608(9) 0.047(3) Uani 1 1 d . . . H29 H 0.9394 1.2015 0.2546 0.056 Uiso 1 1 calc R . . C30 C 1.0220(5) 1.0968(10) 0.2417(8) 0.039(3) Uani 1 1 d . . . C31 C 1.0402(6) 0.9779(10) 0.2386(9) 0.051(3) Uani 1 1 d . . . H31 H 1.0829 0.9546 0.2173 0.061 Uiso 1 1 calc R . . C32 C 0.9923(6) 0.8950(10) 0.2683(8) 0.047(3) Uani 1 1 d . . . H32 H 1.0062 0.8167 0.2716 0.057 Uiso 1 1 calc R . . 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 0.0405(7) 0.0535(7) 0.0559(7) 0.0035(9) -0.0021(8) -0.0047(6) Cl1 0.0638(19) 0.0621(18) 0.090(3) 0.002(2) 0.006(2) 0.0040(15) Cl2 0.0568(19) 0.075(2) 0.0569(18) -0.0008(17) -0.0061(16) 0.0011(17) N1 0.047(6) 0.044(6) 0.080(7) -0.009(6) -0.003(6) -0.008(5) N2 0.023(5) 0.055(6) 0.051(6) -0.004(5) -0.002(4) -0.006(5) N3 0.041(6) 0.044(6) 0.087(8) 0.010(6) -0.002(5) 0.005(5) N4 0.046(7) 0.072(8) 0.106(11) 0.018(8) 0.015(7) 0.013(6) N5 0.084(11) 0.111(13) 0.156(16) 0.009(12) 0.029(11) 0.043(10) N6 0.052(6) 0.042(6) 0.053(6) -0.004(5) -0.004(5) -0.001(5) N7 0.066(7) 0.032(5) 0.058(6) 0.003(5) -0.007(5) -0.001(5) N8 0.076(8) 0.046(6) 0.084(9) -0.007(6) -0.004(6) 0.001(6) N9 0.047(6) 0.039(5) 0.052(6) -0.004(5) 0.009(5) -0.001(5) N10 0.034(6) 0.056(6) 0.071(7) -0.010(5) -0.001(5) 0.008(5) C1 0.037(7) 0.045(7) 0.063(8) -0.006(7) -0.008(6) -0.005(6) C2 0.060(8) 0.050(7) 0.042(7) -0.003(6) -0.003(6) -0.019(6) C3 0.052(7) 0.044(7) 0.046(7) -0.005(6) -0.006(6) -0.011(6) C4 0.028(6) 0.041(7) 0.050(7) -0.010(6) -0.003(5) -0.003(5) C5 0.058(8) 0.060(8) 0.042(7) 0.002(6) -0.010(6) -0.017(7) C6 0.088(11) 0.032(7) 0.073(10) 0.004(7) -0.006(8) -0.015(7) C7 0.052(8) 0.039(7) 0.090(10) 0.004(8) -0.010(8) -0.007(6) C8 0.079(11) 0.053(9) 0.108(13) 0.000(9) -0.040(10) -0.016(8) C9 0.084(13) 0.053(9) 0.146(18) 0.022(12) -0.056(12) -0.012(9) C10 0.047(9) 0.063(10) 0.155(18) 0.026(12) -0.024(11) -0.010(8) C11 0.060(11) 0.041(7) 0.099(13) 0.030(8) 0.006(9) 0.008(7) C12 0.15(2) 0.107(18) 0.19(3) 0.035(18) 0.06(2) 0.051(18) C13 0.17(2) 0.091(13) 0.14(2) 0.000(15) 0.088(19) 0.028(14) C14 0.084(13) 0.100(14) 0.104(15) 0.012(12) 0.028(11) 0.022(11) C15 0.057(8) 0.035(7) 0.073(10) -0.007(7) 0.009(7) -0.006(6) C16 0.054(8) 0.068(9) 0.091(11) -0.024(9) 0.014(7) -0.018(8) C17 0.071(10) 0.064(9) 0.097(12) -0.027(9) 0.035(9) 0.000(8) C18 0.070(10) 0.060(9) 0.057(8) 0.006(7) 0.000(8) -0.012(8) C19 0.049(7) 0.049(8) 0.048(7) 0.002(6) 0.002(6) -0.011(6) C20 0.075(10) 0.045(7) 0.093(11) 0.000(8) -0.004(9) -0.009(7) C21 0.069(9) 0.055(8) 0.071(10) 0.013(8) -0.003(7) -0.012(7) C22 0.057(9) 0.064(9) 0.075(10) 0.000(8) 0.010(7) 0.001(7) C23 0.051(7) 0.047(6) 0.046(8) -0.006(6) -0.011(6) -0.013(5) C24 0.026(6) 0.067(8) 0.058(7) -0.018(6) -0.001(5) 0.005(6) C25 0.024(5) 0.046(6) 0.045(6) -0.001(6) 0.001(5) -0.001(5) C26 0.046(7) 0.045(7) 0.046(7) -0.017(6) -0.002(5) 0.004(6) C27 0.033(6) 0.042(6) 0.063(8) -0.012(6) 0.010(6) -0.006(5) C28 0.041(7) 0.063(8) 0.064(8) 0.018(7) 0.002(6) 0.015(6) C29 0.040(7) 0.043(7) 0.058(7) 0.012(6) -0.001(6) -0.005(6) C30 0.026(6) 0.045(7) 0.047(7) 0.006(6) -0.008(5) -0.004(5) C31 0.045(7) 0.049(7) 0.060(8) -0.006(7) 0.012(6) -0.003(6) C32 0.048(7) 0.041(7) 0.053(7) 0.000(6) -0.001(6) -0.006(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 Zn1 N9 2.019(9) . ? Zn1 N10 2.035(10) . ? Zn1 Cl1 2.208(3) . ? Zn1 Cl2 2.246(4) . ? N1 C15 1.401(15) . ? N1 C7 1.407(15) . ? N1 C1 1.453(14) . ? N2 C25 1.367(12) . ? N2 C30 1.414(14) 3_475 ? N2 C4 1.452(14) . ? N3 C7 1.339(16) . ? N3 C11 1.349(16) . ? N4 C14 1.33(2) . ? N4 N5 1.358(17) . ? N4 C11 1.45(2) . ? N5 C12 1.31(3) . ? N6 C19 1.325(14) . ? N6 C15 1.351(14) . ? N7 N8 1.343(13) . ? N7 C22 1.363(15) . ? N7 C19 1.419(13) . ? N8 C20 1.348(16) . ? N9 C23 1.333(13) . ? N9 C27 1.382(13) . ? N10 C32 1.332(13) . ? N10 C28 1.373(14) . ? C1 C2 1.365(16) . ? C1 C6 1.372(16) . ? C2 C3 1.384(14) . ? C2 H2 0.9300 . ? C3 C4 1.377(15) . ? C3 H3 0.9300 . ? C4 C5 1.382(16) . ? C5 C6 1.383(16) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.393(18) . ? C8 C9 1.38(2) . ? C8 H8 0.9300 . ? C9 C10 1.41(2) . ? C9 H9 0.9300 . ? C10 C11 1.36(2) . ? C10 H10 0.9300 . ? C12 C13 1.39(3) . ? C12 H12 0.9300 . ? C13 C14 1.41(2) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.390(18) . ? C16 C17 1.364(16) . ? C16 H16 0.9300 . ? C17 C18 1.361(17) . ? C17 H17 0.9300 . ? C18 C19 1.379(17) . ? C18 H18 0.9300 . ? C20 C21 1.406(18) . ? C20 H20 0.9300 . ? C21 C22 1.349(17) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.367(14) . ? C23 H23 0.9300 . ? C24 C25 1.432(15) . ? C24 H24 0.9300 . ? C25 C26 1.376(14) . ? C26 C27 1.373(14) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 C29 1.388(15) . ? C28 H28 0.9300 . ? C29 C30 1.387(14) . ? C29 H29 0.9300 . ? C30 C31 1.394(15) . ? C30 N2 1.414(14) 3_575 ? C31 C32 1.395(15) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? 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 N9 Zn1 N10 109.6(4) . . ? N9 Zn1 Cl1 109.6(3) . . ? N10 Zn1 Cl1 108.9(3) . . ? N9 Zn1 Cl2 102.9(3) . . ? N10 Zn1 Cl2 102.0(3) . . ? Cl1 Zn1 Cl2 123.13(16) . . ? C15 N1 C7 122.6(10) . . ? C15 N1 C1 118.3(10) . . ? C7 N1 C1 118.1(10) . . ? C25 N2 C30 123.6(9) . 3_475 ? C25 N2 C4 120.6(9) . . ? C30 N2 C4 115.5(8) 3_475 . ? C7 N3 C11 116.1(12) . . ? C14 N4 N5 111.1(16) . . ? C14 N4 C11 126.4(13) . . ? N5 N4 C11 122.2(16) . . ? C12 N5 N4 105(2) . . ? C19 N6 C15 116.3(10) . . ? N8 N7 C22 111.6(10) . . ? N8 N7 C19 119.7(11) . . ? C22 N7 C19 128.7(10) . . ? N7 N8 C20 103.9(11) . . ? C23 N9 C27 115.4(10) . . ? C23 N9 Zn1 121.1(8) . . ? C27 N9 Zn1 123.4(7) . . ? C32 N10 C28 115.4(10) . . ? C32 N10 Zn1 124.2(8) . . ? C28 N10 Zn1 117.6(8) . . ? C2 C1 C6 120.4(11) . . ? C2 C1 N1 118.1(11) . . ? C6 C1 N1 121.2(11) . . ? C1 C2 C3 120.4(11) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 119.4(11) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 120.1(11) . . ? C3 C4 N2 119.1(10) . . ? C5 C4 N2 120.7(11) . . ? C4 C5 C6 119.7(12) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 119.8(11) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? N3 C7 C8 123.4(13) . . ? N3 C7 N1 114.1(11) . . ? C8 C7 N1 122.4(14) . . ? C9 C8 C7 117.4(16) . . ? C9 C8 H8 121.3 . . ? C7 C8 H8 121.3 . . ? C8 C9 C10 121.5(15) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C11 C10 C9 114.6(15) . . ? C11 C10 H10 122.7 . . ? C9 C10 H10 122.7 . . ? N3 C11 C10 126.9(17) . . ? N3 C11 N4 112.6(13) . . ? C10 C11 N4 120.4(15) . . ? N5 C12 C13 114(2) . . ? N5 C12 H12 122.9 . . ? C13 C12 H12 122.9 . . ? C12 C13 C14 102(3) . . ? C12 C13 H13 129.2 . . ? C14 C13 H13 129.2 . . ? N4 C14 C13 108(2) . . ? N4 C14 H14 125.8 . . ? C13 C14 H14 125.8 . . ? N6 C15 C16 122.6(12) . . ? N6 C15 N1 116.1(11) . . ? C16 C15 N1 121.3(12) . . ? C17 C16 C15 117.6(12) . . ? C17 C16 H16 121.2 . . ? C15 C16 H16 121.2 . . ? C18 C17 C16 121.6(13) . . ? C18 C17 H17 119.2 . . ? C16 C17 H17 119.2 . . ? C17 C18 C19 116.3(13) . . ? C17 C18 H18 121.9 . . ? C19 C18 H18 121.9 . . ? N6 C19 C18 125.2(11) . . ? N6 C19 N7 114.2(10) . . ? C18 C19 N7 120.2(11) . . ? N8 C20 C21 112.1(12) . . ? N8 C20 H20 124.0 . . ? C21 C20 H20 124.0 . . ? C22 C21 C20 103.9(12) . . ? C22 C21 H21 128.0 . . ? C20 C21 H21 128.0 . . ? C21 C22 N7 108.4(12) . . ? C21 C22 H22 125.8 . . ? N7 C22 H22 125.8 . . ? N9 C23 C24 125.0(10) . . ? N9 C23 H23 117.5 . . ? C24 C23 H23 117.5 . . ? C23 C24 C25 120.2(10) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? N2 C25 C26 123.6(10) . . ? N2 C25 C24 121.9(9) . . ? C26 C25 C24 114.4(9) . . ? C27 C26 C25 122.6(10) . . ? C27 C26 H26 118.7 . . ? C25 C26 H26 118.7 . . ? C26 C27 N9 122.4(10) . . ? C26 C27 H27 118.8 . . ? N9 C27 H27 118.8 . . ? N10 C28 C29 123.1(11) . . ? N10 C28 H28 118.5 . . ? C29 C28 H28 118.5 . . ? C30 C29 C28 119.6(11) . . ? C30 C29 H29 120.2 . . ? C28 C29 H29 120.2 . . ? C29 C30 C31 117.9(11) . . ? C29 C30 N2 119.8(10) . 3_575 ? C31 C30 N2 122.2(10) . 3_575 ? C30 C31 C32 117.9(11) . . ? C30 C31 H31 121.0 . . ? C32 C31 H31 121.0 . . ? N10 C32 C31 125.3(11) . . ? N10 C32 H32 117.3 . . ? C31 C32 H32 117.3 . . ? 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 C14 N4 N5 C12 2(2) . . . . ? C11 N4 N5 C12 177.6(16) . . . . ? C22 N7 N8 C20 -2.3(14) . . . . ? C19 N7 N8 C20 178.9(11) . . . . ? N10 Zn1 N9 C23 -91.8(9) . . . . ? Cl1 Zn1 N9 C23 148.7(8) . . . . ? Cl2 Zn1 N9 C23 16.1(8) . . . . ? N10 Zn1 N9 C27 90.5(9) . . . . ? Cl1 Zn1 N9 C27 -29.0(9) . . . . ? Cl2 Zn1 N9 C27 -161.6(8) . . . . ? N9 Zn1 N10 C32 -140.3(9) . . . . ? Cl1 Zn1 N10 C32 -20.4(10) . . . . ? Cl2 Zn1 N10 C32 111.1(9) . . . . ? N9 Zn1 N10 C28 59.2(9) . . . . ? Cl1 Zn1 N10 C28 179.2(8) . . . . ? Cl2 Zn1 N10 C28 -49.3(9) . . . . ? C15 N1 C1 C2 126.5(13) . . . . ? C7 N1 C1 C2 -64.7(16) . . . . ? C15 N1 C1 C6 -60.0(19) . . . . ? C7 N1 C1 C6 108.9(15) . . . . ? C6 C1 C2 C3 -2(2) . . . . ? N1 C1 C2 C3 171.2(11) . . . . ? C1 C2 C3 C4 -1.2(18) . . . . ? C2 C3 C4 C5 4.4(18) . . . . ? C2 C3 C4 N2 -170.6(10) . . . . ? C25 N2 C4 C3 -124.7(11) . . . . ? C30 N2 C4 C3 61.2(15) 3_475 . . . ? C25 N2 C4 C5 60.3(15) . . . . ? C30 N2 C4 C5 -113.8(12) 3_475 . . . ? C3 C4 C5 C6 -4.2(19) . . . . ? N2 C4 C5 C6 170.8(11) . . . . ? C2 C1 C6 C5 3(2) . . . . ? N1 C1 C6 C5 -170.8(11) . . . . ? C4 C5 C6 C1 1(2) . . . . ? C11 N3 C7 C8 1.7(18) . . . . ? C11 N3 C7 N1 177.3(11) . . . . ? C15 N1 C7 N3 139.2(13) . . . . ? C1 N1 C7 N3 -29.1(16) . . . . ? C15 N1 C7 C8 -45(2) . . . . ? C1 N1 C7 C8 146.5(13) . . . . ? N3 C7 C8 C9 0(2) . . . . ? N1 C7 C8 C9 -174.9(13) . . . . ? C7 C8 C9 C10 -1(2) . . . . ? C8 C9 C10 C11 0(2) . . . . ? C7 N3 C11 C10 -3(2) . . . . ? C7 N3 C11 N4 178.7(11) . . . . ? C9 C10 C11 N3 2(2) . . . . ? C9 C10 C11 N4 -179.8(13) . . . . ? C14 N4 C11 N3 -12(2) . . . . ? N5 N4 C11 N3 173.6(13) . . . . ? C14 N4 C11 C10 169.6(15) . . . . ? N5 N4 C11 C10 -5(2) . . . . ? N4 N5 C12 C13 -2(3) . . . . ? N5 C12 C13 C14 1(3) . . . . ? N5 N4 C14 C13 -2(2) . . . . ? C11 N4 C14 C13 -176.9(13) . . . . ? C12 C13 C14 N4 1(2) . . . . ? C19 N6 C15 C16 -1(2) . . . . ? C19 N6 C15 N1 177.7(11) . . . . ? C7 N1 C15 N6 -17(2) . . . . ? C1 N1 C15 N6 151.0(12) . . . . ? C7 N1 C15 C16 161.5(14) . . . . ? C1 N1 C15 C16 -30(2) . . . . ? N6 C15 C16 C17 -1(2) . . . . ? N1 C15 C16 C17 -179.6(15) . . . . ? C15 C16 C17 C18 -1(2) . . . . ? C16 C17 C18 C19 4(2) . . . . ? C15 N6 C19 C18 5.2(19) . . . . ? C15 N6 C19 N7 177.3(10) . . . . ? C17 C18 C19 N6 -7(2) . . . . ? C17 C18 C19 N7 -178.5(13) . . . . ? N8 N7 C19 N6 176.7(10) . . . . ? C22 N7 C19 N6 -1.8(18) . . . . ? N8 N7 C19 C18 -10.7(17) . . . . ? C22 N7 C19 C18 170.8(13) . . . . ? N7 N8 C20 C21 0.7(16) . . . . ? N8 C20 C21 C22 1.1(18) . . . . ? C20 C21 C22 N7 -2.5(16) . . . . ? N8 N7 C22 C21 3.1(15) . . . . ? C19 N7 C22 C21 -178.2(12) . . . . ? C27 N9 C23 C24 2.3(16) . . . . ? Zn1 N9 C23 C24 -175.5(9) . . . . ? N9 C23 C24 C25 -3.6(18) . . . . ? C30 N2 C25 C26 -167.0(11) 3_475 . . . ? C4 N2 C25 C26 19.4(17) . . . . ? C30 N2 C25 C24 17.8(17) 3_475 . . . ? C4 N2 C25 C24 -155.8(11) . . . . ? C23 C24 C25 N2 178.3(10) . . . . ? C23 C24 C25 C26 2.7(16) . . . . ? N2 C25 C26 C27 -176.6(11) . . . . ? C24 C25 C26 C27 -1.1(17) . . . . ? C25 C26 C27 N9 0.0(18) . . . . ? C23 N9 C27 C26 -0.5(15) . . . . ? Zn1 N9 C27 C26 177.3(9) . . . . ? C32 N10 C28 C29 1.5(18) . . . . ? Zn1 N10 C28 C29 163.6(10) . . . . ? N10 C28 C29 C30 -5.3(19) . . . . ? C28 C29 C30 C31 9.1(18) . . . . ? C28 C29 C30 N2 -174.7(11) . . . 3_575 ? C29 C30 C31 C32 -9.2(18) . . . . ? N2 C30 C31 C32 174.7(10) 3_575 . . . ? C28 N10 C32 C31 -1.8(18) . . . . ? Zn1 N10 C32 C31 -162.6(10) . . . . ? C30 C31 C32 N10 5.9(19) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.651 _refine_diff_density_min -1.319 _refine_diff_density_rms 0.102 _database_code_depnum_ccdc_archive 'CCDC 968018' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_111221a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H24 Br2 N10 Zn' _chemical_formula_weight 773.80 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 10.2118(9) _cell_length_b 18.3727(17) _cell_length_c 18.2062(16) _cell_angle_alpha 90.00 _cell_angle_beta 96.2340(10) _cell_angle_gamma 90.00 _cell_volume 3395.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1544 _exptl_absorpt_coefficient_mu 3.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5474 _exptl_absorpt_correction_T_max 0.7887 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'multiwire proportional' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15501 _diffrn_reflns_av_R_equivalents 0.1144 _diffrn_reflns_av_sigmaI/netI 0.1728 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 24.10 _reflns_number_total 5355 _reflns_number_gt 2266 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.1357P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5355 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1663 _refine_ls_R_factor_gt 0.0865 _refine_ls_wR_factor_ref 0.2488 _refine_ls_wR_factor_gt 0.2127 _refine_ls_goodness_of_fit_ref 0.881 _refine_ls_restrained_S_all 0.881 _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 0.44312(14) 0.65703(6) 0.76517(7) 0.0610(5) Uani 1 1 d . . . Br1 Br 0.35199(14) 0.61413(7) 0.87115(7) 0.0802(5) Uani 1 1 d . . . Br2 Br 0.31878(15) 0.72188(7) 0.66896(9) 0.0975(6) Uani 1 1 d . . . N1 N 0.1849(9) 0.2722(4) 0.4050(5) 0.060(2) Uani 1 1 d . . . N2 N 0.5811(9) 0.3589(4) 0.6281(5) 0.054(2) Uani 1 1 d . . . N3 N 0.1169(9) 0.3925(5) 0.4007(5) 0.064(3) Uani 1 1 d . . . N4 N 0.0630(10) 0.5141(5) 0.4039(6) 0.068(3) Uani 1 1 d . . . N5 N -0.0142(11) 0.5723(6) 0.3804(7) 0.090(3) Uani 1 1 d . . . N6 N 0.2474(10) 0.1513(4) 0.4026(5) 0.060(3) Uani 1 1 d . . . N7 N 0.3307(12) 0.0341(5) 0.4029(5) 0.073(3) Uani 1 1 d . . . N8 N 0.3113(14) -0.0404(5) 0.4037(6) 0.094(4) Uani 1 1 d . . . N9 N 0.5004(9) 0.5643(4) 0.7162(4) 0.053(2) Uani 1 1 d . . . N10 N 0.8928(10) 0.2159(4) 0.7015(5) 0.059(2) Uani 1 1 d . . . C1 C 0.2923(12) 0.2916(5) 0.4609(6) 0.057(3) Uani 1 1 d . . . C2 C 0.3884(12) 0.3397(6) 0.4457(6) 0.060(3) Uani 1 1 d . . . H2 H 0.3880 0.3580 0.3980 0.072 Uiso 1 1 calc R . . C3 C 0.4849(11) 0.3613(5) 0.4993(6) 0.054(3) Uani 1 1 d . . . H3 H 0.5490 0.3943 0.4882 0.064 Uiso 1 1 calc R . . C4 C 0.4867(11) 0.3339(5) 0.5699(6) 0.051(3) Uani 1 1 d . . . C5 C 0.3902(11) 0.2835(5) 0.5836(6) 0.056(3) Uani 1 1 d . . . H5 H 0.3919 0.2642 0.6309 0.067 Uiso 1 1 calc R . . C6 C 0.2924(11) 0.2609(5) 0.5305(6) 0.058(3) Uani 1 1 d . . . H6 H 0.2296 0.2269 0.5408 0.069 Uiso 1 1 calc R . . C7 C 0.1110(11) 0.3269(5) 0.3661(6) 0.058(3) Uani 1 1 d . . . C8 C 0.0408(12) 0.3154(6) 0.2997(6) 0.069(3) Uani 1 1 d . . . H8 H 0.0386 0.2695 0.2780 0.082 Uiso 1 1 calc R . . C9 C -0.0278(12) 0.3730(7) 0.2646(7) 0.075(4) Uani 1 1 d . . . H9 H -0.0760 0.3666 0.2187 0.090 Uiso 1 1 calc R . . C10 C -0.0231(13) 0.4403(7) 0.2993(7) 0.074(4) Uani 1 1 d . . . H10 H -0.0703 0.4797 0.2780 0.088 Uiso 1 1 calc R . . C11 C 0.0509(13) 0.4469(6) 0.3639(7) 0.066(3) Uani 1 1 d . . . C12 C 0.0275(17) 0.6211(7) 0.4313(9) 0.092(5) Uani 1 1 d . . . H12 H -0.0072 0.6680 0.4297 0.110 Uiso 1 1 calc R . . C13 C 0.1221(16) 0.6010(7) 0.4858(9) 0.091(4) Uani 1 1 d . . . H13 H 0.1619 0.6278 0.5255 0.109 Uiso 1 1 calc R . . C14 C 0.1428(15) 0.5288(6) 0.4656(8) 0.079(4) Uani 1 1 d . . . H14 H 0.2020 0.4965 0.4906 0.095 Uiso 1 1 calc R . . C15 C 0.1455(14) 0.1987(6) 0.3999(6) 0.063(3) Uani 1 1 d . . . C16 C 0.0144(14) 0.1769(6) 0.3956(7) 0.076(4) Uani 1 1 d . . . H16 H -0.0540 0.2104 0.3943 0.091 Uiso 1 1 calc R . . C17 C -0.0088(15) 0.1033(7) 0.3933(7) 0.086(4) Uani 1 1 d . . . H17 H -0.0954 0.0868 0.3887 0.104 Uiso 1 1 calc R . . C18 C 0.0929(15) 0.0525(7) 0.3975(7) 0.085(4) Uani 1 1 d . . . H18 H 0.0774 0.0026 0.3976 0.102 Uiso 1 1 calc R . . C19 C 0.2183(14) 0.0813(6) 0.4013(6) 0.067(3) Uani 1 1 d . . . C20 C 0.4379(19) -0.0635(8) 0.4046(8) 0.096(5) Uani 1 1 d . . . H20 H 0.4597 -0.1126 0.4057 0.116 Uiso 1 1 calc R . . C21 C 0.5319(16) -0.0099(8) 0.4040(8) 0.095(5) Uani 1 1 d . . . H21 H 0.6224 -0.0155 0.4039 0.114 Uiso 1 1 calc R . . C22 C 0.4605(16) 0.0547(7) 0.4035(7) 0.084(4) Uani 1 1 d . . . H22 H 0.4936 0.1019 0.4037 0.101 Uiso 1 1 calc R . . C23 C 0.4077(12) 0.5211(5) 0.6848(6) 0.063(3) Uani 1 1 d . . . H23 H 0.3211 0.5372 0.6828 0.075 Uiso 1 1 calc R . . C24 C 0.4295(12) 0.4529(5) 0.6541(6) 0.059(3) Uani 1 1 d . . . H24 H 0.3603 0.4256 0.6308 0.071 Uiso 1 1 calc R . . C25 C 0.5579(12) 0.4277(5) 0.6598(6) 0.052(3) Uani 1 1 d . . . C26 C 0.6602(11) 0.4717(5) 0.6916(5) 0.052(3) Uani 1 1 d . . . H26 H 0.7476 0.4571 0.6927 0.062 Uiso 1 1 calc R . . C27 C 0.6273(12) 0.5383(5) 0.7215(6) 0.054(3) Uani 1 1 d . . . H27 H 0.6941 0.5663 0.7462 0.065 Uiso 1 1 calc R . . C28 C 0.8533(12) 0.2701(5) 0.7459(6) 0.063(3) Uani 1 1 d . . . H28 H 0.8961 0.2744 0.7935 0.075 Uiso 1 1 calc R . . C29 C 0.7537(11) 0.3186(5) 0.7240(6) 0.054(3) Uani 1 1 d . . . H29 H 0.7328 0.3555 0.7557 0.065 Uiso 1 1 calc R . . C30 C 0.6849(11) 0.3118(5) 0.6541(6) 0.050(3) Uani 1 1 d . . . C31 C 0.7217(11) 0.2543(5) 0.6089(6) 0.058(3) Uani 1 1 d . . . H31 H 0.6770 0.2465 0.5623 0.069 Uiso 1 1 calc R . . C32 C 0.8268(12) 0.2094(5) 0.6358(6) 0.063(3) Uani 1 1 d . . . H32 H 0.8515 0.1725 0.6051 0.075 Uiso 1 1 calc R . . 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 0.0670(10) 0.0367(7) 0.0759(10) -0.0133(6) -0.0079(7) -0.0008(6) Br1 0.0892(11) 0.0698(8) 0.0818(10) -0.0164(7) 0.0107(8) -0.0035(7) Br2 0.0843(11) 0.0737(9) 0.1262(13) 0.0144(8) -0.0263(10) 0.0072(8) N1 0.073(7) 0.039(5) 0.063(6) 0.007(4) -0.015(5) 0.003(5) N2 0.065(6) 0.037(5) 0.054(6) -0.004(4) -0.018(5) 0.006(4) N3 0.074(7) 0.048(5) 0.067(6) 0.017(5) -0.001(5) 0.007(5) N4 0.076(8) 0.044(6) 0.082(8) 0.019(5) 0.004(6) 0.013(5) N5 0.099(9) 0.060(7) 0.112(9) 0.017(7) 0.009(7) 0.016(7) N6 0.079(7) 0.041(5) 0.058(6) 0.002(4) -0.012(5) -0.004(5) N7 0.098(9) 0.046(6) 0.070(7) -0.007(5) -0.014(6) 0.002(6) N8 0.132(12) 0.050(7) 0.095(9) -0.005(6) -0.012(8) 0.001(7) N9 0.057(6) 0.048(5) 0.052(6) -0.010(4) -0.003(5) -0.004(5) N10 0.085(7) 0.030(4) 0.060(6) 0.004(4) -0.003(6) -0.003(5) C1 0.067(8) 0.036(6) 0.062(8) 0.006(5) -0.014(7) 0.006(6) C2 0.072(9) 0.052(6) 0.052(7) 0.011(6) -0.007(7) 0.000(6) C3 0.067(8) 0.038(5) 0.052(7) 0.009(5) -0.011(6) -0.005(5) C4 0.057(7) 0.036(5) 0.055(7) -0.008(5) -0.017(6) 0.003(5) C5 0.075(9) 0.040(6) 0.050(7) 0.009(5) -0.012(6) 0.002(6) C6 0.070(8) 0.047(6) 0.051(7) 0.009(5) -0.015(6) -0.003(6) C7 0.068(8) 0.047(6) 0.054(7) 0.011(5) -0.011(6) -0.001(6) C8 0.075(9) 0.062(7) 0.064(8) 0.010(6) -0.012(7) 0.003(7) C9 0.074(9) 0.072(8) 0.074(9) 0.015(7) -0.014(7) 0.008(7) C10 0.075(10) 0.066(8) 0.077(9) 0.023(7) -0.002(8) 0.011(7) C11 0.075(9) 0.052(7) 0.072(9) 0.015(6) 0.004(7) 0.001(6) C12 0.112(13) 0.052(8) 0.115(13) 0.011(9) 0.029(11) 0.010(9) C13 0.109(13) 0.063(9) 0.105(12) 0.004(8) 0.029(10) 0.001(8) C14 0.096(11) 0.058(8) 0.085(10) 0.005(7) 0.015(9) -0.002(7) C15 0.074(9) 0.046(7) 0.063(8) -0.003(5) -0.019(7) -0.005(7) C16 0.082(10) 0.056(7) 0.083(9) 0.007(6) -0.019(8) 0.004(7) C17 0.088(11) 0.067(9) 0.099(10) 0.001(7) -0.017(8) -0.011(8) C18 0.098(12) 0.056(7) 0.093(10) -0.002(7) -0.018(9) 0.002(8) C19 0.086(10) 0.046(7) 0.066(8) -0.005(6) -0.011(7) -0.001(7) C20 0.118(14) 0.065(9) 0.103(12) -0.009(8) -0.005(10) 0.009(10) C21 0.104(12) 0.071(9) 0.106(11) -0.020(8) -0.003(9) 0.020(9) C22 0.100(12) 0.061(8) 0.087(10) -0.007(7) -0.009(9) 0.006(8) C23 0.061(8) 0.052(7) 0.073(8) -0.018(6) -0.003(7) -0.001(6) C24 0.062(8) 0.042(6) 0.070(8) -0.019(5) -0.013(6) -0.005(6) C25 0.065(8) 0.036(5) 0.051(7) -0.006(5) -0.006(6) 0.003(6) C26 0.063(8) 0.040(6) 0.051(7) 0.001(5) -0.002(6) 0.006(5) C27 0.063(8) 0.044(6) 0.053(7) 0.000(5) -0.006(6) -0.013(6) C28 0.084(9) 0.045(6) 0.055(7) 0.015(6) -0.013(7) 0.001(6) C29 0.070(8) 0.033(5) 0.054(7) 0.003(5) -0.011(6) 0.008(5) C30 0.063(8) 0.033(5) 0.049(7) 0.002(5) -0.011(6) 0.004(5) C31 0.079(9) 0.036(5) 0.053(7) -0.002(5) -0.014(6) 0.004(6) C32 0.078(9) 0.044(6) 0.061(8) 0.002(5) -0.016(7) 0.014(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 Zn1 N10 2.031(9) 2_656 ? Zn1 N9 2.037(8) . ? Zn1 Br1 2.367(2) . ? Zn1 Br2 2.3699(18) . ? N1 C7 1.402(12) . ? N1 C15 1.410(12) . ? N1 C1 1.457(13) . ? N2 C30 1.409(12) . ? N2 C25 1.419(11) . ? N2 C4 1.429(12) . ? N3 C11 1.343(13) . ? N3 C7 1.358(12) . ? N4 C14 1.341(15) . ? N4 N5 1.370(12) . ? N4 C11 1.432(14) . ? N5 C12 1.326(16) . ? N6 C19 1.320(13) . ? N6 C15 1.354(14) . ? N7 C22 1.377(15) . ? N7 N8 1.382(12) . ? N7 C19 1.437(15) . ? N8 C20 1.358(17) . ? N9 C23 1.318(12) . ? N9 C27 1.374(13) . ? N10 C32 1.313(13) . ? N10 C28 1.371(12) . ? N10 Zn1 2.031(9) 2_646 ? C1 C2 1.371(14) . ? C1 C6 1.387(14) . ? C2 C3 1.369(14) . ? C2 H2 0.9300 . ? C3 C4 1.380(13) . ? C3 H3 0.9300 . ? C4 C5 1.394(14) . ? C5 C6 1.376(14) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.354(14) . ? C8 C9 1.386(14) . ? C8 H8 0.9300 . ? C9 C10 1.387(16) . ? C9 H9 0.9300 . ? C10 C11 1.333(15) . ? C10 H10 0.9300 . ? C12 C13 1.359(18) . ? C12 H12 0.9300 . ? C13 C14 1.399(16) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.391(16) . ? C16 C17 1.373(15) . ? C16 H16 0.9300 . ? C17 C18 1.392(16) . ? C17 H17 0.9300 . ? C18 C19 1.380(16) . ? C18 H18 0.9300 . ? C20 C21 1.376(18) . ? C20 H20 0.9300 . ? C21 C22 1.391(16) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.399(13) . ? C23 H23 0.9300 . ? C24 C25 1.385(14) . ? C24 H24 0.9300 . ? C25 C26 1.396(14) . ? C26 C27 1.395(13) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 C29 1.378(13) . ? C28 H28 0.9300 . ? C29 C30 1.391(13) . ? C29 H29 0.9300 . ? C30 C31 1.416(13) . ? C31 C32 1.399(14) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? 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 N10 Zn1 N9 108.0(4) 2_656 . ? N10 Zn1 Br1 108.6(3) 2_656 . ? N9 Zn1 Br1 103.6(2) . . ? N10 Zn1 Br2 108.2(3) 2_656 . ? N9 Zn1 Br2 104.7(3) . . ? Br1 Zn1 Br2 122.92(8) . . ? C7 N1 C15 121.4(9) . . ? C7 N1 C1 120.0(8) . . ? C15 N1 C1 117.9(8) . . ? C30 N2 C25 124.2(8) . . ? C30 N2 C4 118.3(8) . . ? C25 N2 C4 117.3(8) . . ? C11 N3 C7 115.7(10) . . ? C14 N4 N5 112.4(11) . . ? C14 N4 C11 127.7(10) . . ? N5 N4 C11 119.9(11) . . ? C12 N5 N4 100.3(11) . . ? C19 N6 C15 117.1(11) . . ? C22 N7 N8 114.3(11) . . ? C22 N7 C19 126.9(10) . . ? N8 N7 C19 118.8(12) . . ? C20 N8 N7 99.9(12) . . ? C23 N9 C27 116.6(9) . . ? C23 N9 Zn1 117.8(8) . . ? C27 N9 Zn1 125.0(7) . . ? C32 N10 C28 116.7(9) . . ? C32 N10 Zn1 123.3(7) . 2_646 ? C28 N10 Zn1 119.7(7) . 2_646 ? C2 C1 C6 121.1(10) . . ? C2 C1 N1 121.2(10) . . ? C6 C1 N1 117.7(10) . . ? C3 C2 C1 121.3(10) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 119.6(10) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 118.1(9) . . ? C3 C4 N2 120.9(10) . . ? C5 C4 N2 120.9(9) . . ? C6 C5 C4 123.2(10) . . ? C6 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? C5 C6 C1 116.6(10) . . ? C5 C6 H6 121.7 . . ? C1 C6 H6 121.7 . . ? C8 C7 N3 123.1(10) . . ? C8 C7 N1 122.8(10) . . ? N3 C7 N1 114.1(9) . . ? C7 C8 C9 118.9(11) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C8 C9 C10 118.7(11) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 118.1(11) . . ? C11 C10 H10 121.0 . . ? C9 C10 H10 121.0 . . ? C10 C11 N3 125.3(11) . . ? C10 C11 N4 122.5(11) . . ? N3 C11 N4 112.1(11) . . ? N5 C12 C13 118.4(13) . . ? N5 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? C12 C13 C14 100.4(14) . . ? C12 C13 H13 129.8 . . ? C14 C13 H13 129.8 . . ? N4 C14 C13 108.5(13) . . ? N4 C14 H14 125.8 . . ? C13 C14 H14 125.8 . . ? N6 C15 C16 123.3(10) . . ? N6 C15 N1 113.6(11) . . ? C16 C15 N1 123.1(11) . . ? C17 C16 C15 116.5(12) . . ? C17 C16 H16 121.7 . . ? C15 C16 H16 121.7 . . ? C16 C17 C18 122.2(13) . . ? C16 C17 H17 118.9 . . ? C18 C17 H17 118.9 . . ? C19 C18 C17 115.4(12) . . ? C19 C18 H18 122.3 . . ? C17 C18 H18 122.3 . . ? N6 C19 C18 125.5(13) . . ? N6 C19 N7 114.2(12) . . ? C18 C19 N7 120.3(11) . . ? N8 C20 C21 116.1(13) . . ? N8 C20 H20 121.9 . . ? C21 C20 H20 121.9 . . ? C20 C21 C22 104.1(14) . . ? C20 C21 H21 127.9 . . ? C22 C21 H21 127.9 . . ? N7 C22 C21 105.6(12) . . ? N7 C22 H22 127.2 . . ? C21 C22 H22 127.2 . . ? N9 C23 C24 125.1(11) . . ? N9 C23 H23 117.4 . . ? C24 C23 H23 117.4 . . ? C25 C24 C23 117.4(10) . . ? C25 C24 H24 121.3 . . ? C23 C24 H24 121.3 . . ? C24 C25 C26 119.8(9) . . ? C24 C25 N2 117.8(9) . . ? C26 C25 N2 122.3(10) . . ? C27 C26 C25 118.0(10) . . ? C27 C26 H26 121.0 . . ? C25 C26 H26 121.0 . . ? N9 C27 C26 122.9(10) . . ? N9 C27 H27 118.5 . . ? C26 C27 H27 118.5 . . ? N10 C28 C29 123.6(10) . . ? N10 C28 H28 118.2 . . ? C29 C28 H28 118.2 . . ? C28 C29 C30 119.4(10) . . ? C28 C29 H29 120.3 . . ? C30 C29 H29 120.3 . . ? C29 C30 N2 122.7(9) . . ? C29 C30 C31 117.3(9) . . ? N2 C30 C31 120.0(9) . . ? C32 C31 C30 118.6(10) . . ? C32 C31 H31 120.7 . . ? C30 C31 H31 120.7 . . ? N10 C32 C31 124.3(10) . . ? N10 C32 H32 117.9 . . ? C31 C32 H32 117.9 . . ? 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 C14 N4 N5 C12 0.9(14) . . . . ? C11 N4 N5 C12 -179.9(11) . . . . ? C22 N7 N8 C20 -0.2(14) . . . . ? C19 N7 N8 C20 179.7(10) . . . . ? N10 Zn1 N9 C23 -174.2(8) 2_656 . . . ? Br1 Zn1 N9 C23 70.8(8) . . . . ? Br2 Zn1 N9 C23 -59.1(8) . . . . ? N10 Zn1 N9 C27 14.7(9) 2_656 . . . ? Br1 Zn1 N9 C27 -100.4(8) . . . . ? Br2 Zn1 N9 C27 129.7(8) . . . . ? C7 N1 C1 C2 -51.0(15) . . . . ? C15 N1 C1 C2 138.7(11) . . . . ? C7 N1 C1 C6 127.6(11) . . . . ? C15 N1 C1 C6 -42.8(14) . . . . ? C6 C1 C2 C3 -2.5(16) . . . . ? N1 C1 C2 C3 176.0(9) . . . . ? C1 C2 C3 C4 0.6(16) . . . . ? C2 C3 C4 C5 1.2(15) . . . . ? C2 C3 C4 N2 -176.0(9) . . . . ? C30 N2 C4 C3 -107.6(11) . . . . ? C25 N2 C4 C3 77.2(13) . . . . ? C30 N2 C4 C5 75.4(13) . . . . ? C25 N2 C4 C5 -99.8(11) . . . . ? C3 C4 C5 C6 -1.1(16) . . . . ? N2 C4 C5 C6 176.0(9) . . . . ? C4 C5 C6 C1 -0.7(16) . . . . ? C2 C1 C6 C5 2.5(15) . . . . ? N1 C1 C6 C5 -176.1(9) . . . . ? C11 N3 C7 C8 -1.8(17) . . . . ? C11 N3 C7 N1 177.8(10) . . . . ? C15 N1 C7 C8 -31.7(17) . . . . ? C1 N1 C7 C8 158.4(11) . . . . ? C15 N1 C7 N3 148.7(11) . . . . ? C1 N1 C7 N3 -21.3(15) . . . . ? N3 C7 C8 C9 0.6(19) . . . . ? N1 C7 C8 C9 -179.0(11) . . . . ? C7 C8 C9 C10 -0.7(19) . . . . ? C8 C9 C10 C11 2.1(19) . . . . ? C9 C10 C11 N3 -4(2) . . . . ? C9 C10 C11 N4 179.7(11) . . . . ? C7 N3 C11 C10 3.5(18) . . . . ? C7 N3 C11 N4 -179.6(10) . . . . ? C14 N4 C11 C10 -173.6(12) . . . . ? N5 N4 C11 C10 7.3(18) . . . . ? C14 N4 C11 N3 9.4(18) . . . . ? N5 N4 C11 N3 -169.6(10) . . . . ? N4 N5 C12 C13 -0.7(17) . . . . ? N5 C12 C13 C14 0.3(18) . . . . ? N5 N4 C14 C13 -0.8(15) . . . . ? C11 N4 C14 C13 -179.9(11) . . . . ? C12 C13 C14 N4 0.3(15) . . . . ? C19 N6 C15 C16 -0.4(17) . . . . ? C19 N6 C15 N1 177.2(9) . . . . ? C7 N1 C15 N6 144.9(10) . . . . ? C1 N1 C15 N6 -44.9(14) . . . . ? C7 N1 C15 C16 -37.5(17) . . . . ? C1 N1 C15 C16 132.6(12) . . . . ? N6 C15 C16 C17 -0.6(18) . . . . ? N1 C15 C16 C17 -178.0(10) . . . . ? C15 C16 C17 C18 2.1(19) . . . . ? C16 C17 C18 C19 -2(2) . . . . ? C15 N6 C19 C18 0.1(18) . . . . ? C15 N6 C19 N7 178.9(9) . . . . ? C17 C18 C19 N6 1(2) . . . . ? C17 C18 C19 N7 -177.5(11) . . . . ? C22 N7 C19 N6 -1.7(17) . . . . ? N8 N7 C19 N6 178.3(9) . . . . ? C22 N7 C19 C18 177.1(12) . . . . ? N8 N7 C19 C18 -2.9(17) . . . . ? N7 N8 C20 C21 -0.4(16) . . . . ? N8 C20 C21 C22 0.8(18) . . . . ? N8 N7 C22 C21 0.7(15) . . . . ? C19 N7 C22 C21 -179.2(11) . . . . ? C20 C21 C22 N7 -0.9(15) . . . . ? C27 N9 C23 C24 -2.7(16) . . . . ? Zn1 N9 C23 C24 -174.6(9) . . . . ? N9 C23 C24 C25 2.6(17) . . . . ? C23 C24 C25 C26 -3.4(16) . . . . ? C23 C24 C25 N2 -179.3(9) . . . . ? C30 N2 C25 C24 -151.0(10) . . . . ? C4 N2 C25 C24 23.9(14) . . . . ? C30 N2 C25 C26 33.2(15) . . . . ? C4 N2 C25 C26 -152.0(10) . . . . ? C24 C25 C26 C27 4.5(15) . . . . ? N2 C25 C26 C27 -179.7(9) . . . . ? C23 N9 C27 C26 3.9(15) . . . . ? Zn1 N9 C27 C26 175.1(7) . . . . ? C25 C26 C27 N9 -4.9(15) . . . . ? C32 N10 C28 C29 -2.8(16) . . . . ? Zn1 N10 C28 C29 171.5(8) 2_646 . . . ? N10 C28 C29 C30 2.3(16) . . . . ? C28 C29 C30 N2 179.4(9) . . . . ? C28 C29 C30 C31 0.2(15) . . . . ? C25 N2 C30 C29 17.4(16) . . . . ? C4 N2 C30 C29 -157.5(10) . . . . ? C25 N2 C30 C31 -163.4(10) . . . . ? C4 N2 C30 C31 21.8(14) . . . . ? C29 C30 C31 C32 -2.0(15) . . . . ? N2 C30 C31 C32 178.8(10) . . . . ? C28 N10 C32 C31 0.8(16) . . . . ? Zn1 N10 C32 C31 -173.3(8) 2_646 . . . ? C30 C31 C32 N10 1.5(17) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 24.10 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.942 _refine_diff_density_min -0.995 _refine_diff_density_rms 0.129 _database_code_depnum_ccdc_archive 'CCDC 968019' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_111201b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H24 I2 N10 Zn' _chemical_formula_weight 867.78 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 10.5859(7) _cell_length_b 16.9380(14) _cell_length_c 19.398(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.5450(10) _cell_angle_gamma 90.00 _cell_volume 3455.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.668 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1688 _exptl_absorpt_coefficient_mu 2.535 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4976 _exptl_absorpt_correction_T_max 0.6181 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'multiwire proportional' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13805 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.0801 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6065 _reflns_number_gt 3553 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.1119P)^2^+19.2371P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6065 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1330 _refine_ls_R_factor_gt 0.0818 _refine_ls_wR_factor_ref 0.2499 _refine_ls_wR_factor_gt 0.2048 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.001 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 0.56155(10) 0.32834(7) 0.20157(7) 0.0518(4) Uani 1 1 d . . . I1 I 0.61494(10) 0.39491(6) 0.09010(6) 0.0871(4) Uani 1 1 d . . . I2 I 0.72111(9) 0.23891(7) 0.27076(6) 0.1011(5) Uani 1 1 d . . . N1 N 0.7812(8) 0.6958(5) 0.6011(4) 0.047(2) Uani 1 1 d . . . N2 N 0.4309(7) 0.6289(5) 0.3663(4) 0.0395(19) Uani 1 1 d . . . N3 N 0.8555(7) 0.5689(5) 0.5853(5) 0.047(2) Uani 1 1 d . . . N4 N 0.9154(8) 0.4424(5) 0.5593(6) 0.056(2) Uani 1 1 d . . . N5 N 0.9875(11) 0.3763(7) 0.5732(7) 0.077(3) Uani 1 1 d . . . N6 N 0.7222(7) 0.8270(5) 0.6078(4) 0.046(2) Uani 1 1 d . . . N7 N 0.6448(10) 0.9544(6) 0.6051(5) 0.064(3) Uani 1 1 d . . . N8 N 0.6605(13) 1.0336(7) 0.6102(7) 0.085(3) Uani 1 1 d . . . N9 N 0.5141(7) 0.4208(5) 0.2632(4) 0.043(2) Uani 1 1 d . . . N10 N 0.1118(7) 0.7729(5) 0.3163(5) 0.044(2) Uani 1 1 d . . . C1 C 0.6881(8) 0.6811(6) 0.5412(5) 0.038(2) Uani 1 1 d . . . C2 C 0.5901(9) 0.6290(7) 0.5465(5) 0.050(3) Uani 1 1 d . . . H2 H 0.5803 0.6056 0.5889 0.061 Uiso 1 1 calc R . . C3 C 0.5064(9) 0.6117(6) 0.4888(5) 0.045(2) Uani 1 1 d . . . H3 H 0.4427 0.5743 0.4914 0.054 Uiso 1 1 calc R . . C4 C 0.5177(8) 0.6499(5) 0.4276(5) 0.035(2) Uani 1 1 d . . . C5 C 0.6131(9) 0.7055(6) 0.4223(5) 0.042(2) Uani 1 1 d . . . H5 H 0.6195 0.7319 0.3808 0.051 Uiso 1 1 calc R . . C6 C 0.6975(9) 0.7202(6) 0.4803(5) 0.046(3) Uani 1 1 d . . . H6 H 0.7618 0.7572 0.4780 0.055 Uiso 1 1 calc R . . C7 C 0.8570(8) 0.6323(7) 0.6264(5) 0.047(3) Uani 1 1 d . . . C8 C 0.9259(11) 0.6326(8) 0.6928(6) 0.066(3) Uani 1 1 d . . . H8 H 0.9242 0.6758 0.7224 0.080 Uiso 1 1 calc R . . C9 C 0.9970(12) 0.5654(10) 0.7124(7) 0.078(4) Uani 1 1 d . . . H9 H 1.0459 0.5645 0.7553 0.094 Uiso 1 1 calc R . . C10 C 0.9969(11) 0.5005(9) 0.6702(8) 0.074(4) Uani 1 1 d . . . H10 H 1.0438 0.4556 0.6837 0.089 Uiso 1 1 calc R . . C11 C 0.9246(9) 0.5051(7) 0.6076(6) 0.053(3) Uani 1 1 d . . . C12 C 0.9560(14) 0.3315(9) 0.5192(10) 0.087(5) Uani 1 1 d . . . H12 H 0.9876 0.2808 0.5146 0.105 Uiso 1 1 calc R . . C13 C 0.8708(13) 0.3675(8) 0.4695(8) 0.076(4) Uani 1 1 d . . . H13 H 0.8383 0.3468 0.4267 0.091 Uiso 1 1 calc R . . C14 C 0.8435(11) 0.4406(8) 0.4966(7) 0.065(3) Uani 1 1 d . . . H14 H 0.7889 0.4793 0.4765 0.078 Uiso 1 1 calc R . . C15 C 0.8182(9) 0.7756(6) 0.6133(5) 0.044(2) Uani 1 1 d . . . C16 C 0.9456(10) 0.8001(7) 0.6258(6) 0.060(3) Uani 1 1 d . . . H16 H 1.0115 0.7635 0.6309 0.072 Uiso 1 1 calc R . . C17 C 0.9695(12) 0.8799(8) 0.6302(6) 0.064(3) Uani 1 1 d . . . H17 H 1.0528 0.8980 0.6383 0.077 Uiso 1 1 calc R . . C18 C 0.8726(12) 0.9321(8) 0.6228(6) 0.067(3) Uani 1 1 d . . . H18 H 0.8880 0.9861 0.6257 0.080 Uiso 1 1 calc R . . C19 C 0.7511(11) 0.9036(7) 0.6109(6) 0.052(3) Uani 1 1 d . . . C20 C 0.547(2) 1.0598(11) 0.6002(9) 0.100(5) Uani 1 1 d . . . H20 H 0.5278 1.1134 0.5997 0.120 Uiso 1 1 calc R . . C21 C 0.4542(18) 1.0017(13) 0.5903(10) 0.115(6) Uani 1 1 d . . . H21 H 0.3665 1.0080 0.5824 0.138 Uiso 1 1 calc R . . C22 C 0.5218(14) 0.9337(9) 0.5947(8) 0.081(4) Uani 1 1 d . . . H22 H 0.4893 0.8827 0.5913 0.097 Uiso 1 1 calc R . . C23 C 0.6061(10) 0.4669(7) 0.2963(7) 0.063(3) Uani 1 1 d . . . H23 H 0.6902 0.4511 0.2961 0.075 Uiso 1 1 calc R . . C24 C 0.5824(9) 0.5358(7) 0.3301(7) 0.060(3) Uani 1 1 d . . . H24 H 0.6489 0.5658 0.3519 0.072 Uiso 1 1 calc R . . C25 C 0.4554(8) 0.5597(5) 0.3312(5) 0.037(2) Uani 1 1 d . . . C26 C 0.3618(8) 0.5111(5) 0.2997(5) 0.037(2) Uani 1 1 d . . . H26 H 0.2767 0.5240 0.3010 0.045 Uiso 1 1 calc R . . C27 C 0.3938(9) 0.4440(6) 0.2665(5) 0.042(2) Uani 1 1 d . . . H27 H 0.3286 0.4127 0.2450 0.051 Uiso 1 1 calc R . . C28 C 0.1494(10) 0.7229(6) 0.2698(5) 0.048(3) Uani 1 1 d . . . H28 H 0.1024 0.7200 0.2263 0.058 Uiso 1 1 calc R . . C29 C 0.2538(9) 0.6755(6) 0.2829(5) 0.043(2) Uani 1 1 d . . . H29 H 0.2771 0.6420 0.2485 0.052 Uiso 1 1 calc R . . C30 C 0.3265(8) 0.6772(6) 0.3486(5) 0.037(2) Uani 1 1 d . . . C31 C 0.2908(9) 0.7341(6) 0.3947(6) 0.047(3) Uani 1 1 d . . . H31 H 0.3385 0.7408 0.4376 0.056 Uiso 1 1 calc R . . C32 C 0.1847(9) 0.7803(6) 0.3766(6) 0.047(3) Uani 1 1 d . . . H32 H 0.1632 0.8182 0.4079 0.057 Uiso 1 1 calc R . . 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 0.0363(6) 0.0466(7) 0.0706(9) -0.0217(7) -0.0017(6) -0.0043(5) I1 0.0918(7) 0.0646(6) 0.1138(9) -0.0182(6) 0.0501(6) -0.0154(5) I2 0.0687(6) 0.0974(8) 0.1258(10) -0.0181(7) -0.0378(6) 0.0248(5) N1 0.046(5) 0.045(5) 0.044(5) 0.002(4) -0.015(4) -0.004(4) N2 0.039(4) 0.044(5) 0.032(4) -0.004(4) -0.012(3) 0.008(4) N3 0.041(4) 0.046(5) 0.051(6) 0.014(5) -0.001(4) -0.003(4) N4 0.052(5) 0.045(5) 0.074(7) 0.018(5) 0.015(5) 0.008(4) N5 0.075(7) 0.060(7) 0.099(10) 0.024(7) 0.025(7) 0.018(6) N6 0.040(4) 0.064(6) 0.032(5) -0.006(4) -0.007(3) -0.002(4) N7 0.081(7) 0.058(6) 0.052(6) -0.013(5) 0.003(5) 0.001(5) N8 0.100(9) 0.054(7) 0.100(10) -0.013(7) 0.010(7) 0.009(6) N9 0.033(4) 0.042(4) 0.051(5) -0.014(4) -0.008(4) 0.000(3) N10 0.043(4) 0.042(5) 0.047(5) 0.010(4) -0.001(4) -0.002(4) C1 0.032(5) 0.042(5) 0.036(6) -0.005(5) -0.015(4) 0.002(4) C2 0.049(6) 0.064(7) 0.036(6) 0.009(5) -0.007(4) -0.001(5) C3 0.044(5) 0.036(5) 0.052(7) 0.008(5) -0.007(5) -0.008(4) C4 0.029(4) 0.030(5) 0.042(6) -0.002(4) -0.008(4) 0.004(4) C5 0.049(5) 0.041(5) 0.035(6) 0.009(5) 0.000(4) -0.006(4) C6 0.042(5) 0.040(5) 0.050(7) 0.005(5) -0.012(4) -0.010(4) C7 0.030(5) 0.066(7) 0.042(6) 0.014(6) -0.010(4) -0.003(5) C8 0.061(7) 0.072(8) 0.058(8) 0.002(7) -0.031(6) -0.001(6) C9 0.059(7) 0.112(12) 0.057(8) 0.042(9) -0.023(6) 0.002(8) C10 0.047(7) 0.084(10) 0.088(10) 0.032(9) -0.003(7) 0.007(7) C11 0.034(5) 0.067(8) 0.057(7) 0.025(6) 0.002(5) 0.004(5) C12 0.088(10) 0.051(8) 0.129(15) 0.048(10) 0.035(10) 0.030(7) C13 0.089(9) 0.061(8) 0.085(10) -0.011(8) 0.047(8) -0.010(7) C14 0.050(6) 0.069(8) 0.077(9) 0.014(7) 0.008(6) -0.005(6) C15 0.039(5) 0.059(6) 0.031(6) -0.006(5) -0.005(4) 0.000(5) C16 0.043(6) 0.065(7) 0.069(8) -0.014(7) -0.009(5) 0.000(5) C17 0.057(7) 0.072(8) 0.059(8) -0.025(7) -0.009(6) -0.010(6) C18 0.074(8) 0.061(8) 0.065(8) -0.022(7) -0.001(6) -0.012(6) C19 0.063(7) 0.051(7) 0.041(6) -0.002(5) -0.004(5) 0.002(5) C20 0.127(15) 0.079(11) 0.092(13) -0.002(10) 0.008(11) 0.025(11) C21 0.087(11) 0.137(17) 0.119(15) 0.004(13) 0.006(10) 0.048(12) C22 0.078(9) 0.066(9) 0.098(11) 0.003(8) 0.006(8) 0.011(7) C23 0.036(5) 0.063(7) 0.086(9) -0.034(7) -0.008(5) 0.005(5) C24 0.038(5) 0.056(7) 0.081(9) -0.029(6) -0.013(5) 0.002(5) C25 0.042(5) 0.036(5) 0.031(5) -0.002(4) -0.003(4) 0.004(4) C26 0.032(4) 0.038(5) 0.040(6) -0.001(5) -0.004(4) -0.005(4) C27 0.042(5) 0.046(6) 0.037(6) 0.000(5) -0.004(4) -0.006(4) C28 0.051(6) 0.055(6) 0.034(6) 0.007(5) -0.014(4) 0.006(5) C29 0.043(5) 0.045(6) 0.039(6) 0.000(5) -0.002(4) 0.009(4) C30 0.036(5) 0.040(5) 0.033(5) 0.004(4) -0.004(4) 0.003(4) C31 0.040(5) 0.051(6) 0.044(6) -0.003(5) -0.015(4) 0.008(4) C32 0.038(5) 0.048(6) 0.054(7) -0.003(5) -0.002(5) 0.008(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 N10 2.055(8) 2_545 ? Zn1 N9 2.067(8) . ? Zn1 I2 2.5362(16) . ? Zn1 I1 2.5583(18) . ? N1 C7 1.396(13) . ? N1 C15 1.420(13) . ? N1 C1 1.457(11) . ? N2 C30 1.387(11) . ? N2 C25 1.394(12) . ? N2 C4 1.463(11) . ? N3 C7 1.337(14) . ? N3 C11 1.349(13) . ? N4 C14 1.360(16) . ? N4 N5 1.364(13) . ? N4 C11 1.413(15) . ? N5 C12 1.307(19) . ? N6 C19 1.333(14) . ? N6 C15 1.333(13) . ? N7 C22 1.341(17) . ? N7 N8 1.354(15) . ? N7 C19 1.412(15) . ? N8 C20 1.27(2) . ? N9 C27 1.341(12) . ? N9 C23 1.351(12) . ? N10 C32 1.331(13) . ? N10 C28 1.332(13) . ? N10 Zn1 2.055(8) 2 ? C1 C6 1.369(14) . ? C1 C2 1.374(14) . ? C2 C3 1.378(14) . ? C2 H2 0.9300 . ? C3 C4 1.368(14) . ? C3 H3 0.9300 . ? C4 C5 1.393(13) . ? C5 C6 1.377(13) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.407(14) . ? C8 C9 1.394(18) . ? C8 H8 0.9300 . ? C9 C10 1.37(2) . ? C9 H9 0.9300 . ? C10 C11 1.361(17) . ? C10 H10 0.9300 . ? C12 C13 1.38(2) . ? C12 H12 0.9300 . ? C13 C14 1.388(18) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.405(14) . ? C16 C17 1.378(17) . ? C16 H16 0.9300 . ? C17 C18 1.349(17) . ? C17 H17 0.9300 . ? C18 C19 1.368(16) . ? C18 H18 0.9300 . ? C20 C21 1.39(2) . ? C20 H20 0.9300 . ? C21 C22 1.35(2) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.376(15) . ? C23 H23 0.9300 . ? C24 C25 1.407(13) . ? C24 H24 0.9300 . ? C25 C26 1.376(12) . ? C26 C27 1.369(14) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 C29 1.366(14) . ? C28 H28 0.9300 . ? C29 C30 1.412(13) . ? C29 H29 0.9300 . ? C30 C31 1.395(14) . ? C31 C32 1.382(13) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? 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 N10 Zn1 N9 100.0(3) 2_545 . ? N10 Zn1 I2 110.1(2) 2_545 . ? N9 Zn1 I2 109.7(2) . . ? N10 Zn1 I1 109.7(3) 2_545 . ? N9 Zn1 I1 104.3(3) . . ? I2 Zn1 I1 120.83(6) . . ? C7 N1 C15 122.6(8) . . ? C7 N1 C1 117.3(8) . . ? C15 N1 C1 116.3(8) . . ? C30 N2 C25 124.3(7) . . ? C30 N2 C4 117.8(8) . . ? C25 N2 C4 117.8(7) . . ? C7 N3 C11 118.9(9) . . ? C14 N4 N5 113.8(12) . . ? C14 N4 C11 126.9(10) . . ? N5 N4 C11 119.3(11) . . ? C12 N5 N4 103.4(11) . . ? C19 N6 C15 117.5(9) . . ? C22 N7 N8 112.3(12) . . ? C22 N7 C19 127.2(11) . . ? N8 N7 C19 120.6(11) . . ? C20 N8 N7 103.2(13) . . ? C27 N9 C23 116.5(8) . . ? C27 N9 Zn1 122.9(6) . . ? C23 N9 Zn1 120.2(7) . . ? C32 N10 C28 117.8(9) . . ? C32 N10 Zn1 121.5(7) . 2 ? C28 N10 Zn1 120.4(6) . 2 ? C6 C1 C2 120.3(8) . . ? C6 C1 N1 119.8(9) . . ? C2 C1 N1 119.9(9) . . ? C1 C2 C3 119.9(10) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 119.4(9) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 121.3(8) . . ? C3 C4 N2 118.8(8) . . ? C5 C4 N2 119.8(9) . . ? C6 C5 C4 118.0(9) . . ? C6 C5 H5 121.0 . . ? C4 C5 H5 121.0 . . ? C1 C6 C5 120.9(9) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? N3 C7 N1 116.2(8) . . ? N3 C7 C8 121.2(11) . . ? N1 C7 C8 122.5(11) . . ? C9 C8 C7 117.0(13) . . ? C9 C8 H8 121.5 . . ? C7 C8 H8 121.5 . . ? C10 C9 C8 122.0(11) . . ? C10 C9 H9 119.0 . . ? C8 C9 H9 119.0 . . ? C11 C10 C9 116.7(12) . . ? C11 C10 H10 121.7 . . ? C9 C10 H10 121.7 . . ? N3 C11 C10 124.1(13) . . ? N3 C11 N4 113.3(9) . . ? C10 C11 N4 122.6(12) . . ? N5 C12 C13 112.9(12) . . ? N5 C12 H12 123.5 . . ? C13 C12 H12 123.5 . . ? C12 C13 C14 106.0(14) . . ? C12 C13 H13 127.0 . . ? C14 C13 H13 127.0 . . ? N4 C14 C13 103.8(12) . . ? N4 C14 H14 128.1 . . ? C13 C14 H14 128.1 . . ? N6 C15 C16 122.0(10) . . ? N6 C15 N1 114.5(8) . . ? C16 C15 N1 123.4(10) . . ? C17 C16 C15 117.8(11) . . ? C17 C16 H16 121.1 . . ? C15 C16 H16 121.1 . . ? C18 C17 C16 120.3(11) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C17 C18 C19 118.4(12) . . ? C17 C18 H18 120.8 . . ? C19 C18 H18 120.8 . . ? N6 C19 C18 123.9(11) . . ? N6 C19 N7 114.4(10) . . ? C18 C19 N7 121.6(11) . . ? N8 C20 C21 114.5(16) . . ? N8 C20 H20 122.7 . . ? C21 C20 H20 122.7 . . ? C22 C21 C20 103.5(15) . . ? C22 C21 H21 128.2 . . ? C20 C21 H21 128.2 . . ? N7 C22 C21 106.5(15) . . ? N7 C22 H22 126.7 . . ? C21 C22 H22 126.7 . . ? N9 C23 C24 123.7(9) . . ? N9 C23 H23 118.1 . . ? C24 C23 H23 118.1 . . ? C23 C24 C25 118.6(9) . . ? C23 C24 H24 120.7 . . ? C25 C24 H24 120.7 . . ? C26 C25 N2 123.7(8) . . ? C26 C25 C24 117.5(9) . . ? N2 C25 C24 118.7(8) . . ? C27 C26 C25 120.1(9) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? N9 C27 C26 123.5(9) . . ? N9 C27 H27 118.3 . . ? C26 C27 H27 118.3 . . ? N10 C28 C29 123.1(9) . . ? N10 C28 H28 118.4 . . ? C29 C28 H28 118.4 . . ? C28 C29 C30 120.1(10) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? N2 C30 C31 121.0(8) . . ? N2 C30 C29 123.2(9) . . ? C31 C30 C29 115.7(8) . . ? C32 C31 C30 120.0(9) . . ? C32 C31 H31 120.0 . . ? C30 C31 H31 120.0 . . ? N10 C32 C31 122.9(10) . . ? N10 C32 H32 118.5 . . ? C31 C32 H32 118.5 . . ? 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 C14 N4 N5 C12 -2.4(14) . . . . ? C11 N4 N5 C12 179.9(10) . . . . ? C22 N7 N8 C20 -2.4(17) . . . . ? C19 N7 N8 C20 178.0(12) . . . . ? N10 Zn1 N9 C27 -17.9(9) 2_545 . . . ? I2 Zn1 N9 C27 -133.6(7) . . . . ? I1 Zn1 N9 C27 95.6(8) . . . . ? N10 Zn1 N9 C23 169.9(9) 2_545 . . . ? I2 Zn1 N9 C23 54.2(9) . . . . ? I1 Zn1 N9 C23 -76.6(9) . . . . ? C7 N1 C1 C6 -117.3(11) . . . . ? C15 N1 C1 C6 41.3(13) . . . . ? C7 N1 C1 C2 63.8(13) . . . . ? C15 N1 C1 C2 -137.6(10) . . . . ? C6 C1 C2 C3 4.9(16) . . . . ? N1 C1 C2 C3 -176.3(10) . . . . ? C1 C2 C3 C4 -3.6(16) . . . . ? C2 C3 C4 C5 0.6(15) . . . . ? C2 C3 C4 N2 177.9(9) . . . . ? C30 N2 C4 C3 99.1(11) . . . . ? C25 N2 C4 C3 -78.1(11) . . . . ? C30 N2 C4 C5 -83.6(11) . . . . ? C25 N2 C4 C5 99.2(11) . . . . ? C3 C4 C5 C6 1.1(15) . . . . ? N2 C4 C5 C6 -176.2(9) . . . . ? C2 C1 C6 C5 -3.1(16) . . . . ? N1 C1 C6 C5 178.0(10) . . . . ? C4 C5 C6 C1 0.2(16) . . . . ? C11 N3 C7 N1 -178.6(9) . . . . ? C11 N3 C7 C8 -1.9(15) . . . . ? C15 N1 C7 N3 -143.9(10) . . . . ? C1 N1 C7 N3 13.3(13) . . . . ? C15 N1 C7 C8 39.5(15) . . . . ? C1 N1 C7 C8 -163.4(10) . . . . ? N3 C7 C8 C9 2.9(17) . . . . ? N1 C7 C8 C9 179.3(10) . . . . ? C7 C8 C9 C10 -2(2) . . . . ? C8 C9 C10 C11 1(2) . . . . ? C7 N3 C11 C10 0.2(16) . . . . ? C7 N3 C11 N4 -179.7(9) . . . . ? C9 C10 C11 N3 0.5(18) . . . . ? C9 C10 C11 N4 -179.6(11) . . . . ? C14 N4 C11 N3 -1.9(15) . . . . ? N5 N4 C11 N3 175.5(9) . . . . ? C14 N4 C11 C10 178.2(11) . . . . ? N5 N4 C11 C10 -4.4(16) . . . . ? N4 N5 C12 C13 2.7(15) . . . . ? N5 C12 C13 C14 -2.2(16) . . . . ? N5 N4 C14 C13 1.1(13) . . . . ? C11 N4 C14 C13 178.6(10) . . . . ? C12 C13 C14 N4 0.6(13) . . . . ? C19 N6 C15 C16 3.6(15) . . . . ? C19 N6 C15 N1 -172.7(9) . . . . ? C7 N1 C15 N6 -157.6(9) . . . . ? C1 N1 C15 N6 45.0(13) . . . . ? C7 N1 C15 C16 26.2(16) . . . . ? C1 N1 C15 C16 -131.2(11) . . . . ? N6 C15 C16 C17 -2.1(17) . . . . ? N1 C15 C16 C17 173.9(10) . . . . ? C15 C16 C17 C18 0.2(19) . . . . ? C16 C17 C18 C19 -0.1(19) . . . . ? C15 N6 C19 C18 -3.5(17) . . . . ? C15 N6 C19 N7 -179.8(9) . . . . ? C17 C18 C19 N6 1.7(19) . . . . ? C17 C18 C19 N7 177.8(11) . . . . ? C22 N7 C19 N6 -2.3(18) . . . . ? N8 N7 C19 N6 177.3(10) . . . . ? C22 N7 C19 C18 -178.7(13) . . . . ? N8 N7 C19 C18 0.9(17) . . . . ? N7 N8 C20 C21 2(2) . . . . ? N8 C20 C21 C22 0(2) . . . . ? N8 N7 C22 C21 2.3(17) . . . . ? C19 N7 C22 C21 -178.0(13) . . . . ? C20 C21 C22 N7 -1.2(19) . . . . ? C27 N9 C23 C24 -2.1(18) . . . . ? Zn1 N9 C23 C24 170.5(11) . . . . ? N9 C23 C24 C25 1(2) . . . . ? C30 N2 C25 C26 -32.2(15) . . . . ? C4 N2 C25 C26 144.8(9) . . . . ? C30 N2 C25 C24 150.7(10) . . . . ? C4 N2 C25 C24 -32.3(14) . . . . ? C23 C24 C25 C26 1.8(17) . . . . ? C23 C24 C25 N2 179.1(11) . . . . ? N2 C25 C26 C27 -179.7(9) . . . . ? C24 C25 C26 C27 -2.6(15) . . . . ? C23 N9 C27 C26 1.3(15) . . . . ? Zn1 N9 C27 C26 -171.1(8) . . . . ? C25 C26 C27 N9 1.1(15) . . . . ? C32 N10 C28 C29 4.5(16) . . . . ? Zn1 N10 C28 C29 -169.9(8) 2 . . . ? N10 C28 C29 C30 1.0(16) . . . . ? C25 N2 C30 C31 164.3(10) . . . . ? C4 N2 C30 C31 -12.7(14) . . . . ? C25 N2 C30 C29 -19.0(15) . . . . ? C4 N2 C30 C29 164.0(9) . . . . ? C28 C29 C30 N2 177.7(9) . . . . ? C28 C29 C30 C31 -5.4(15) . . . . ? N2 C30 C31 C32 -178.5(9) . . . . ? C29 C30 C31 C32 4.6(15) . . . . ? C28 N10 C32 C31 -5.4(16) . . . . ? Zn1 N10 C32 C31 168.9(8) 2 . . . ? C30 C31 C32 N10 0.7(17) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.629 _refine_diff_density_min -1.780 _refine_diff_density_rms 0.152 _database_code_depnum_ccdc_archive 'CCDC 968020' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_121121f _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C64 H48 Cd Cl2 N20' _chemical_formula_weight 1280.52 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.8210(5) _cell_length_b 44.970(3) _cell_length_c 11.0991(9) _cell_angle_alpha 90.00 _cell_angle_beta 134.490(2) _cell_angle_gamma 90.00 _cell_volume 2784.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3903 _cell_measurement_theta_min 2.612 _cell_measurement_theta_max 26.672 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1308 _exptl_absorpt_coefficient_mu 0.553 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7891 _exptl_absorpt_correction_T_max 0.9367 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13778 _diffrn_reflns_av_R_equivalents 0.0963 _diffrn_reflns_av_sigmaI/netI 0.0986 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -53 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4909 _reflns_number_gt 3564 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.0532P)^2^+8.9738P] 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 4909 _refine_ls_number_parameters 394 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1047 _refine_ls_R_factor_gt 0.0782 _refine_ls_wR_factor_ref 0.1932 _refine_ls_wR_factor_gt 0.1815 _refine_ls_goodness_of_fit_ref 1.178 _refine_ls_restrained_S_all 1.178 _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 Cd1 Cd 1.5000 0.5000 0.0000 0.0282(2) Uani 1 2 d S . . Cl1 Cl 1.0491(3) 0.49962(5) -0.1964(2) 0.0443(5) Uani 1 1 d . . . N1 N 0.5864(10) 0.66077(12) -0.0036(7) 0.0280(13) Uani 1 1 d . . . N2 N 1.3174(10) 0.57464(12) 0.4122(6) 0.0256(13) Uani 1 1 d . . . N3 N 0.3252(10) 0.69506(13) -0.0396(6) 0.0274(13) Uani 1 1 d . . . N4 N 0.0650(10) 0.72982(13) -0.0886(7) 0.0314(14) Uani 1 1 d . . . N5 N -0.0399(12) 0.74390(16) -0.0464(8) 0.0467(18) Uani 1 1 d . . . N6 N 0.6928(9) 0.65633(11) -0.1507(6) 0.0233(12) Uani 1 1 d . . . N7 N 0.8253(10) 0.64800(14) -0.2782(7) 0.0340(15) Uani 1 1 d . . . N8 N 0.8527(14) 0.65549(18) -0.3821(8) 0.055(2) Uani 1 1 d . . . N9 N 1.5320(11) 0.53467(14) 0.1910(7) 0.0374(16) Uani 1 1 d . . . N10 N 1.4627(10) 0.53820(12) 0.8271(6) 0.0271(13) Uani 1 1 d . . . C1 C 0.7705(12) 0.63836(15) 0.1054(8) 0.0257(15) Uani 1 1 d . . . C2 C 0.7226(12) 0.60866(15) 0.0556(8) 0.0310(17) Uani 1 1 d . . . H2 H 0.5724 0.6031 -0.0470 0.037 Uiso 1 1 calc R . . C3 C 0.8991(12) 0.58768(15) 0.1590(8) 0.0295(16) Uani 1 1 d . . . H3 H 0.8674 0.5677 0.1277 0.035 Uiso 1 1 calc R . . C4 C 1.1234(12) 0.59624(14) 0.3096(7) 0.0233(15) Uani 1 1 d . . . C5 C 1.1667(12) 0.62535(15) 0.3611(8) 0.0290(16) Uani 1 1 d . . . H5 H 1.3158 0.6310 0.4645 0.035 Uiso 1 1 calc R . . C6 C 0.9874(13) 0.64622(15) 0.2586(8) 0.0298(16) Uani 1 1 d . . . H6 H 1.0152 0.6659 0.2946 0.036 Uiso 1 1 calc R . . C7 C 0.4653(12) 0.67114(14) 0.0408(8) 0.0240(15) Uani 1 1 d . . . C8 C 0.4952(13) 0.65626(17) 0.1652(9) 0.0375(18) Uani 1 1 d . . . H8 H 0.5881 0.6392 0.2170 0.045 Uiso 1 1 calc R . . C9 C 0.3802(14) 0.66813(17) 0.2078(9) 0.0364(18) Uani 1 1 d . . . H9 H 0.4029 0.6593 0.2938 0.044 Uiso 1 1 calc R . . C10 C 0.2357(13) 0.69225(18) 0.1284(9) 0.0375(18) Uani 1 1 d . . . H10 H 0.1566 0.7001 0.1559 0.045 Uiso 1 1 calc R . . C11 C 0.2138(11) 0.70449(15) 0.0039(7) 0.0265(15) Uani 1 1 d . . . C12 C -0.1720(16) 0.7649(2) -0.1640(11) 0.055(2) Uani 1 1 d . . . H12 H -0.2669 0.7782 -0.1681 0.066 Uiso 1 1 calc R . . C13 C -0.1543(16) 0.76488(19) -0.2773(11) 0.053(2) Uani 1 1 d . . . H13 H -0.2297 0.7777 -0.3684 0.063 Uiso 1 1 calc R . . C14 C -0.0013(14) 0.74199(16) -0.2284(9) 0.042(2) Uani 1 1 d . . . H14 H 0.0476 0.7360 -0.2805 0.050 Uiso 1 1 calc R . . C15 C 0.5614(12) 0.67151(16) -0.1351(8) 0.0291(16) Uani 1 1 d . . . C16 C 0.4224(17) 0.69611(19) -0.2387(11) 0.056(3) Uani 1 1 d . . . H16 H 0.3303 0.7065 -0.2285 0.067 Uiso 1 1 calc R . . C17 C 0.4277(17) 0.70416(18) -0.3548(11) 0.053(2) Uani 1 1 d . . . H17 H 0.3341 0.7201 -0.4258 0.064 Uiso 1 1 calc R . . C18 C 0.5623(14) 0.68996(16) -0.3708(9) 0.0369(18) Uani 1 1 d . . . H18 H 0.5703 0.6961 -0.4467 0.044 Uiso 1 1 calc R . . C19 C 0.6891(12) 0.66533(16) -0.2656(8) 0.0301(16) Uani 1 1 d . . . C20 C 0.9706(17) 0.6331(2) -0.3710(11) 0.062(3) Uani 1 1 d . . . H20 H 1.0131 0.6318 -0.4308 0.074 Uiso 1 1 calc R . . C21 C 1.0231(17) 0.6119(2) -0.2616(11) 0.062(3) Uani 1 1 d . . . H21 H 1.1094 0.5945 -0.2318 0.074 Uiso 1 1 calc R . . C22 C 0.9259(16) 0.6210(2) -0.2049(10) 0.051(2) Uani 1 1 d . . . H22 H 0.9271 0.6110 -0.1311 0.062 Uiso 1 1 calc R . . C23 C 1.4077(14) 0.56058(18) 0.1351(9) 0.040(2) Uani 1 1 d . . . H23 H 1.3629 0.5693 0.0404 0.048 Uiso 1 1 calc R . . C24 C 1.3436(14) 0.57473(17) 0.2071(9) 0.0360(18) Uani 1 1 d . . . H24 H 1.2594 0.5926 0.1621 0.043 Uiso 1 1 calc R . . C25 C 1.4044(12) 0.56243(14) 0.3481(7) 0.0239(15) Uani 1 1 d . . . C26 C 1.5384(11) 0.53644(14) 0.4092(7) 0.0241(15) Uani 1 1 d . . . H26 H 1.5849 0.5270 0.5030 0.029 Uiso 1 1 calc R . . C27 C 1.6020(12) 0.52469(15) 0.3314(8) 0.0281(16) Uani 1 1 d . . . H27 H 1.7032 0.5083 0.3820 0.034 Uiso 1 1 calc R . . C28 C 1.6366(12) 0.54136(14) 0.8286(7) 0.0252(15) Uani 1 1 d . . . H28 H 1.7897 0.5346 0.9225 0.030 Uiso 1 1 calc R . . C29 C 1.5996(12) 0.55398(14) 0.6999(7) 0.0225(14) Uani 1 1 d . . . H29 H 1.7272 0.5565 0.7099 0.027 Uiso 1 1 calc R . . C30 C 1.3701(12) 0.56308(14) 0.5536(8) 0.0225(14) Uani 1 1 d . . . C31 C 1.1901(12) 0.56066(14) 0.5522(8) 0.0248(15) Uani 1 1 d . . . H31 H 1.0359 0.5676 0.4608 0.030 Uiso 1 1 calc R . . C32 C 1.2464(13) 0.54785(15) 0.6889(8) 0.0298(16) Uani 1 1 d . . . H32 H 1.1236 0.5458 0.6843 0.036 Uiso 1 1 calc R . . 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 Cd1 0.0319(4) 0.0310(4) 0.0248(3) 0.0094(3) 0.0210(3) 0.0107(4) Cl1 0.0312(10) 0.0557(12) 0.0417(9) 0.0266(10) 0.0240(9) 0.0181(10) N1 0.036(3) 0.021(3) 0.035(3) 0.014(2) 0.028(3) 0.017(3) N2 0.032(3) 0.024(3) 0.025(3) 0.014(2) 0.022(3) 0.015(3) N3 0.028(3) 0.029(3) 0.024(3) 0.005(2) 0.018(3) 0.005(3) N4 0.038(4) 0.025(3) 0.039(3) 0.003(3) 0.030(3) 0.011(3) N5 0.052(4) 0.050(4) 0.051(4) 0.005(3) 0.041(4) 0.017(3) N6 0.030(3) 0.017(3) 0.022(3) 0.002(2) 0.017(3) 0.005(2) N7 0.037(4) 0.040(4) 0.028(3) 0.005(3) 0.024(3) 0.007(3) N8 0.067(5) 0.075(6) 0.041(4) 0.011(4) 0.045(4) 0.018(4) N9 0.052(4) 0.038(4) 0.036(3) 0.014(3) 0.035(3) 0.023(3) N10 0.040(4) 0.022(3) 0.021(3) 0.003(2) 0.022(3) 0.010(3) C1 0.032(4) 0.028(4) 0.029(3) 0.011(3) 0.026(3) 0.011(3) C2 0.029(4) 0.026(4) 0.027(3) 0.003(3) 0.015(3) 0.006(3) C3 0.039(4) 0.017(3) 0.027(3) -0.003(3) 0.021(3) 0.003(3) C4 0.032(4) 0.019(3) 0.023(3) 0.009(3) 0.021(3) 0.012(3) C5 0.028(4) 0.027(4) 0.026(3) 0.002(3) 0.017(3) 0.000(3) C6 0.042(4) 0.015(3) 0.036(4) 0.003(3) 0.028(4) 0.006(3) C7 0.027(4) 0.015(3) 0.028(3) -0.004(3) 0.019(3) -0.002(3) C8 0.041(4) 0.035(4) 0.042(4) 0.015(3) 0.031(4) 0.011(4) C9 0.049(5) 0.033(4) 0.040(4) 0.006(3) 0.035(4) 0.000(4) C10 0.044(5) 0.047(5) 0.035(4) 0.004(4) 0.032(4) 0.003(4) C11 0.023(4) 0.028(4) 0.020(3) -0.001(3) 0.012(3) 0.006(3) C12 0.057(6) 0.049(5) 0.063(5) 0.014(5) 0.043(5) 0.029(5) C13 0.059(6) 0.044(5) 0.056(5) 0.025(4) 0.041(5) 0.030(4) C14 0.057(5) 0.031(4) 0.049(5) 0.008(4) 0.041(4) 0.010(4) C15 0.037(4) 0.028(4) 0.028(3) 0.007(3) 0.025(3) 0.009(3) C16 0.088(7) 0.050(5) 0.070(6) 0.038(5) 0.070(6) 0.045(5) C17 0.092(7) 0.037(5) 0.063(5) 0.032(4) 0.066(6) 0.033(5) C18 0.057(5) 0.026(4) 0.041(4) 0.010(3) 0.039(4) 0.006(4) C19 0.032(4) 0.030(4) 0.028(3) -0.006(3) 0.021(3) -0.004(3) C20 0.060(6) 0.095(8) 0.048(5) 0.002(5) 0.045(5) 0.021(6) C21 0.069(6) 0.062(6) 0.059(6) 0.007(5) 0.047(5) 0.030(5) C22 0.066(6) 0.051(5) 0.052(5) 0.010(4) 0.047(5) 0.018(5) C23 0.056(5) 0.045(5) 0.037(4) 0.019(4) 0.039(4) 0.017(4) C24 0.051(5) 0.034(4) 0.041(4) 0.025(3) 0.039(4) 0.024(4) C25 0.033(4) 0.024(4) 0.020(3) -0.003(3) 0.020(3) 0.003(3) C26 0.030(4) 0.023(4) 0.019(3) 0.006(3) 0.017(3) 0.008(3) C27 0.033(4) 0.028(4) 0.031(3) 0.004(3) 0.026(3) 0.013(3) C28 0.031(4) 0.019(3) 0.019(3) -0.001(3) 0.015(3) 0.006(3) C29 0.030(4) 0.022(3) 0.021(3) 0.007(3) 0.020(3) 0.006(3) C30 0.033(4) 0.014(3) 0.027(3) 0.007(3) 0.024(3) 0.006(3) C31 0.027(4) 0.024(4) 0.024(3) 0.010(3) 0.018(3) 0.012(3) C32 0.042(4) 0.024(4) 0.037(4) 0.005(3) 0.033(4) 0.011(3) _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 Cd1 N10 2.436(5) 1_554 ? Cd1 N10 2.436(5) 3_866 ? Cd1 N9 2.499(6) . ? Cd1 N9 2.499(6) 3_865 ? Cd1 Cl1 2.5323(17) 3_865 ? Cd1 Cl1 2.5323(17) . ? N1 C15 1.415(8) . ? N1 C7 1.418(8) . ? N1 C1 1.453(8) . ? N2 C25 1.396(8) . ? N2 C30 1.413(7) . ? N2 C4 1.456(8) . ? N3 C11 1.328(8) . ? N3 C7 1.336(8) . ? N4 N5 1.353(8) . ? N4 C14 1.360(9) . ? N4 C11 1.425(8) . ? N5 C12 1.331(10) . ? N6 C19 1.320(8) . ? N6 C15 1.342(8) . ? N7 N8 1.354(8) . ? N7 C22 1.362(10) . ? N7 C19 1.404(9) . ? N8 C20 1.313(11) . ? N9 C27 1.316(8) . ? N9 C23 1.357(9) . ? N10 C32 1.329(8) . ? N10 C28 1.356(9) . ? N10 Cd1 2.436(5) 1_556 ? C1 C6 1.361(9) . ? C1 C2 1.393(9) . ? C2 C3 1.376(9) . ? C2 H2 0.9300 . ? C3 C4 1.382(9) . ? C3 H3 0.9300 . ? C4 C5 1.373(9) . ? C5 C6 1.380(9) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.399(9) . ? C8 C9 1.382(10) . ? C8 H8 0.9300 . ? C9 C10 1.354(10) . ? C9 H9 0.9300 . ? C10 C11 1.381(9) . ? C10 H10 0.9300 . ? C12 C13 1.359(12) . ? C12 H12 0.9300 . ? C13 C14 1.370(11) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.406(10) . ? C16 C17 1.366(10) . ? C16 H16 0.9300 . ? C17 C18 1.345(11) . ? C17 H17 0.9300 . ? C18 C19 1.396(10) . ? C18 H18 0.9300 . ? C20 C21 1.360(13) . ? C20 H20 0.9300 . ? C21 C22 1.346(12) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.362(10) . ? C23 H23 0.9300 . ? C24 C25 1.393(9) . ? C24 H24 0.9300 . ? C25 C26 1.388(9) . ? C26 C27 1.369(9) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 C29 1.366(8) . ? C28 H28 0.9300 . ? C29 C30 1.393(9) . ? C29 H29 0.9300 . ? C30 C31 1.401(9) . ? C31 C32 1.375(9) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? 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 N10 Cd1 N10 180.00(18) 1_554 3_866 ? N10 Cd1 N9 96.55(18) 1_554 . ? N10 Cd1 N9 83.45(18) 3_866 . ? N10 Cd1 N9 83.45(18) 1_554 3_865 ? N10 Cd1 N9 96.55(18) 3_866 3_865 ? N9 Cd1 N9 180.0(2) . 3_865 ? N10 Cd1 Cl1 89.95(14) 1_554 3_865 ? N10 Cd1 Cl1 90.05(14) 3_866 3_865 ? N9 Cd1 Cl1 90.81(16) . 3_865 ? N9 Cd1 Cl1 89.19(16) 3_865 3_865 ? N10 Cd1 Cl1 90.05(14) 1_554 . ? N10 Cd1 Cl1 89.95(14) 3_866 . ? N9 Cd1 Cl1 89.19(16) . . ? N9 Cd1 Cl1 90.81(16) 3_865 . ? Cl1 Cd1 Cl1 180.0 3_865 . ? C15 N1 C7 127.1(5) . . ? C15 N1 C1 115.8(5) . . ? C7 N1 C1 116.9(5) . . ? C25 N2 C30 123.6(5) . . ? C25 N2 C4 118.5(5) . . ? C30 N2 C4 116.6(5) . . ? C11 N3 C7 117.0(6) . . ? N5 N4 C14 111.6(6) . . ? N5 N4 C11 120.8(6) . . ? C14 N4 C11 127.6(6) . . ? C12 N5 N4 103.6(6) . . ? C19 N6 C15 118.0(6) . . ? N8 N7 C22 111.1(7) . . ? N8 N7 C19 122.0(6) . . ? C22 N7 C19 126.6(6) . . ? C20 N8 N7 104.4(7) . . ? C27 N9 C23 113.8(6) . . ? C27 N9 Cd1 120.2(5) . . ? C23 N9 Cd1 122.2(4) . . ? C32 N10 C28 115.7(6) . . ? C32 N10 Cd1 119.5(5) . 1_556 ? C28 N10 Cd1 119.9(4) . 1_556 ? C6 C1 C2 119.9(6) . . ? C6 C1 N1 120.0(6) . . ? C2 C1 N1 120.1(6) . . ? C3 C2 C1 119.5(6) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 119.9(6) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 120.2(6) . . ? C5 C4 N2 119.5(6) . . ? C3 C4 N2 120.3(6) . . ? C4 C5 C6 119.6(6) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C1 C6 C5 120.7(6) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? N3 C7 C8 122.4(6) . . ? N3 C7 N1 117.9(6) . . ? C8 C7 N1 119.7(6) . . ? C9 C8 C7 117.0(7) . . ? C9 C8 H8 121.5 . . ? C7 C8 H8 121.5 . . ? C10 C9 C8 122.2(7) . . ? C10 C9 H9 118.9 . . ? C8 C9 H9 118.9 . . ? C9 C10 C11 115.6(7) . . ? C9 C10 H10 122.2 . . ? C11 C10 H10 122.2 . . ? N3 C11 C10 125.7(6) . . ? N3 C11 N4 114.0(6) . . ? C10 C11 N4 120.4(6) . . ? N5 C12 C13 113.3(7) . . ? N5 C12 H12 123.4 . . ? C13 C12 H12 123.4 . . ? C12 C13 C14 105.1(7) . . ? C12 C13 H13 127.4 . . ? C14 C13 H13 127.4 . . ? N4 C14 C13 106.5(7) . . ? N4 C14 H14 126.8 . . ? C13 C14 H14 126.8 . . ? N6 C15 C16 121.2(6) . . ? N6 C15 N1 113.2(5) . . ? C16 C15 N1 125.5(6) . . ? C17 C16 C15 117.6(7) . . ? C17 C16 H16 121.2 . . ? C15 C16 H16 121.2 . . ? C18 C17 C16 122.9(7) . . ? C18 C17 H17 118.6 . . ? C16 C17 H17 118.6 . . ? C17 C18 C19 115.4(7) . . ? C17 C18 H18 122.3 . . ? C19 C18 H18 122.3 . . ? N6 C19 C18 124.9(7) . . ? N6 C19 N7 115.0(6) . . ? C18 C19 N7 120.1(6) . . ? N8 C20 C21 112.0(8) . . ? N8 C20 H20 124.0 . . ? C21 C20 H20 124.0 . . ? C22 C21 C20 106.7(8) . . ? C22 C21 H21 126.7 . . ? C20 C21 H21 126.7 . . ? C21 C22 N7 105.7(8) . . ? C21 C22 H22 127.1 . . ? N7 C22 H22 127.1 . . ? N9 C23 C24 124.9(6) . . ? N9 C23 H23 117.5 . . ? C24 C23 H23 117.5 . . ? C23 C24 C25 119.9(6) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C26 C25 C24 115.4(6) . . ? C26 C25 N2 123.6(6) . . ? C24 C25 N2 120.8(6) . . ? C27 C26 C25 120.0(6) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? N9 C27 C26 125.6(6) . . ? N9 C27 H27 117.2 . . ? C26 C27 H27 117.2 . . ? N10 C28 C29 123.7(6) . . ? N10 C28 H28 118.1 . . ? C29 C28 H28 118.1 . . ? C28 C29 C30 119.8(6) . . ? C28 C29 H29 120.1 . . ? C30 C29 H29 120.1 . . ? C29 C30 C31 117.0(6) . . ? C29 C30 N2 122.5(6) . . ? C31 C30 N2 120.5(6) . . ? C32 C31 C30 118.5(6) . . ? C32 C31 H31 120.7 . . ? C30 C31 H31 120.7 . . ? N10 C32 C31 125.1(7) . . ? N10 C32 H32 117.5 . . ? C31 C32 H32 117.5 . . ? 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 C14 N4 N5 C12 0.1(9) . . . . ? C11 N4 N5 C12 -176.7(7) . . . . ? C22 N7 N8 C20 -0.2(10) . . . . ? C19 N7 N8 C20 -174.6(7) . . . . ? N10 Cd1 N9 C27 -166.9(6) 1_554 . . . ? N10 Cd1 N9 C27 13.1(6) 3_866 . . . ? N9 Cd1 N9 C27 -69(100) 3_865 . . . ? Cl1 Cd1 N9 C27 -76.8(6) 3_865 . . . ? Cl1 Cd1 N9 C27 103.2(6) . . . . ? N10 Cd1 N9 C23 36.2(6) 1_554 . . . ? N10 Cd1 N9 C23 -143.8(6) 3_866 . . . ? N9 Cd1 N9 C23 134(100) 3_865 . . . ? Cl1 Cd1 N9 C23 126.2(6) 3_865 . . . ? Cl1 Cd1 N9 C23 -53.8(6) . . . . ? C15 N1 C1 C6 99.8(7) . . . . ? C7 N1 C1 C6 -75.4(8) . . . . ? C15 N1 C1 C2 -82.2(8) . . . . ? C7 N1 C1 C2 102.6(7) . . . . ? C6 C1 C2 C3 -2.7(10) . . . . ? N1 C1 C2 C3 179.3(6) . . . . ? C1 C2 C3 C4 -1.3(11) . . . . ? C2 C3 C4 C5 3.9(10) . . . . ? C2 C3 C4 N2 -174.3(6) . . . . ? C25 N2 C4 C5 -112.0(7) . . . . ? C30 N2 C4 C5 80.6(8) . . . . ? C25 N2 C4 C3 66.2(8) . . . . ? C30 N2 C4 C3 -101.2(7) . . . . ? C3 C4 C5 C6 -2.4(10) . . . . ? N2 C4 C5 C6 175.7(6) . . . . ? C2 C1 C6 C5 4.1(10) . . . . ? N1 C1 C6 C5 -177.9(6) . . . . ? C4 C5 C6 C1 -1.6(11) . . . . ? C11 N3 C7 C8 0.3(9) . . . . ? C11 N3 C7 N1 -179.8(6) . . . . ? C15 N1 C7 N3 -5.6(10) . . . . ? C1 N1 C7 N3 169.0(6) . . . . ? C15 N1 C7 C8 174.3(7) . . . . ? C1 N1 C7 C8 -11.1(9) . . . . ? N3 C7 C8 C9 -2.6(10) . . . . ? N1 C7 C8 C9 177.5(6) . . . . ? C7 C8 C9 C10 3.0(11) . . . . ? C8 C9 C10 C11 -1.0(11) . . . . ? C7 N3 C11 C10 2.0(10) . . . . ? C7 N3 C11 N4 -179.2(6) . . . . ? C9 C10 C11 N3 -1.7(11) . . . . ? C9 C10 C11 N4 179.6(7) . . . . ? N5 N4 C11 N3 -172.9(6) . . . . ? C14 N4 C11 N3 10.8(10) . . . . ? N5 N4 C11 C10 6.0(10) . . . . ? C14 N4 C11 C10 -170.4(7) . . . . ? N4 N5 C12 C13 -0.5(10) . . . . ? N5 C12 C13 C14 0.6(12) . . . . ? N5 N4 C14 C13 0.2(9) . . . . ? C11 N4 C14 C13 176.8(7) . . . . ? C12 C13 C14 N4 -0.5(10) . . . . ? C19 N6 C15 C16 0.5(10) . . . . ? C19 N6 C15 N1 -177.5(6) . . . . ? C7 N1 C15 N6 -177.4(6) . . . . ? C1 N1 C15 N6 8.0(9) . . . . ? C7 N1 C15 C16 4.8(12) . . . . ? C1 N1 C15 C16 -169.8(8) . . . . ? N6 C15 C16 C17 -0.5(13) . . . . ? N1 C15 C16 C17 177.1(8) . . . . ? C15 C16 C17 C18 -1.3(15) . . . . ? C16 C17 C18 C19 2.9(13) . . . . ? C15 N6 C19 C18 1.4(10) . . . . ? C15 N6 C19 N7 -178.4(6) . . . . ? C17 C18 C19 N6 -3.1(11) . . . . ? C17 C18 C19 N7 176.7(7) . . . . ? N8 N7 C19 N6 -175.5(6) . . . . ? C22 N7 C19 N6 11.1(10) . . . . ? N8 N7 C19 C18 4.7(10) . . . . ? C22 N7 C19 C18 -168.7(8) . . . . ? N7 N8 C20 C21 -1.2(11) . . . . ? N8 C20 C21 C22 2.1(12) . . . . ? C20 C21 C22 N7 -2.1(11) . . . . ? N8 N7 C22 C21 1.5(10) . . . . ? C19 N7 C22 C21 175.5(7) . . . . ? C27 N9 C23 C24 -4.1(12) . . . . ? Cd1 N9 C23 C24 154.2(7) . . . . ? N9 C23 C24 C25 -0.6(13) . . . . ? C23 C24 C25 C26 2.5(11) . . . . ? C23 C24 C25 N2 -172.6(7) . . . . ? C30 N2 C25 C26 4.7(10) . . . . ? C4 N2 C25 C26 -161.8(6) . . . . ? C30 N2 C25 C24 179.3(7) . . . . ? C4 N2 C25 C24 12.9(9) . . . . ? C24 C25 C26 C27 0.2(10) . . . . ? N2 C25 C26 C27 175.1(6) . . . . ? C23 N9 C27 C26 7.1(11) . . . . ? Cd1 N9 C27 C26 -151.6(6) . . . . ? C25 C26 C27 N9 -5.4(11) . . . . ? C32 N10 C28 C29 1.0(9) . . . . ? Cd1 N10 C28 C29 156.3(5) 1_556 . . . ? N10 C28 C29 C30 -3.2(10) . . . . ? C28 C29 C30 C31 4.6(9) . . . . ? C28 C29 C30 N2 -176.2(6) . . . . ? C25 N2 C30 C29 43.5(9) . . . . ? C4 N2 C30 C29 -149.9(6) . . . . ? C25 N2 C30 C31 -137.4(7) . . . . ? C4 N2 C30 C31 29.3(9) . . . . ? C29 C30 C31 C32 -4.1(9) . . . . ? N2 C30 C31 C32 176.7(6) . . . . ? C28 N10 C32 C31 -0.5(10) . . . . ? Cd1 N10 C32 C31 -156.0(5) 1_556 . . . ? C30 C31 C32 N10 2.2(10) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.881 _refine_diff_density_min -1.358 _refine_diff_density_rms 0.102 _database_code_depnum_ccdc_archive 'CCDC 968021' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_130110c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C64 H48 Br2 Cd N20' _chemical_formula_weight 1369.44 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 7.9001(7) _cell_length_b 44.620(3) _cell_length_c 8.0308(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.642(2) _cell_angle_gamma 90.00 _cell_volume 2829.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1738 _cell_measurement_theta_min 2.5321 _cell_measurement_theta_max 28.3518 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1380 _exptl_absorpt_coefficient_mu 1.862 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6051 _exptl_absorpt_correction_T_max 0.8075 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9442 _diffrn_reflns_av_R_equivalents 0.0511 _diffrn_reflns_av_sigmaI/netI 0.0867 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -53 _diffrn_reflns_limit_k_max 45 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 25.02 _reflns_number_total 5000 _reflns_number_gt 3086 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.0307P)^2^+0.5213P] 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 5000 _refine_ls_number_parameters 394 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0983 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1215 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 Cd1 Cd 0.5000 0.5000 1.5000 0.02548(17) Uani 1 2 d S . . Br1 Br 0.23653(7) 0.501121(16) 1.69977(6) 0.0393(2) Uani 1 1 d . . . N1 N 0.4052(5) 0.66207(10) 0.4931(5) 0.0276(11) Uani 1 1 d . . . N2 N 0.0939(5) 0.57648(11) 0.9069(5) 0.0271(11) Uani 1 1 d . . . N3 N 0.6319(5) 0.69554(10) 0.4548(5) 0.0253(11) Uani 1 1 d . . . N4 N 0.8453(6) 0.72959(11) 0.4037(5) 0.0317(12) Uani 1 1 d . . . N5 N 0.9912(6) 0.74344(13) 0.4469(6) 0.0476(15) Uani 1 1 d . . . N6 N 0.1512(5) 0.65783(11) 0.3454(5) 0.0283(11) Uani 1 1 d . . . N7 N -0.1081(6) 0.64939(12) 0.2155(5) 0.0347(12) Uani 1 1 d . . . N8 N -0.2380(7) 0.65715(15) 0.1087(6) 0.0576(17) Uani 1 1 d . . . N9 N 0.3636(6) 0.53892(11) 1.3198(5) 0.0270(11) Uani 1 1 d . . . N10 N -0.3418(6) 0.53583(12) 0.6856(5) 0.0366(13) Uani 1 1 d . . . C1 C 0.3315(6) 0.63940(13) 0.6018(6) 0.0272(13) Uani 1 1 d . . . C2 C 0.2708(7) 0.64816(13) 0.7539(6) 0.0301(14) Uani 1 1 d . . . H2 H 0.2806 0.6680 0.7883 0.036 Uiso 1 1 calc R . . C3 C 0.1957(7) 0.62733(13) 0.8539(6) 0.0296(14) Uani 1 1 d . . . H3 H 0.1531 0.6331 0.9557 0.036 Uiso 1 1 calc R . . C4 C 0.1833(6) 0.59791(12) 0.8041(6) 0.0225(12) Uani 1 1 d . . . C5 C 0.2506(7) 0.58874(13) 0.6557(6) 0.0315(14) Uani 1 1 d . . . H5 H 0.2464 0.5687 0.6242 0.038 Uiso 1 1 calc R . . C6 C 0.3247(7) 0.61001(14) 0.5540(6) 0.0326(15) Uani 1 1 d . . . H6 H 0.3696 0.6042 0.4532 0.039 Uiso 1 1 calc R . . C7 C 0.5692(7) 0.67171(13) 0.5369(6) 0.0243(13) Uani 1 1 d . . . C8 C 0.6655(7) 0.65702(15) 0.6626(7) 0.0371(16) Uani 1 1 d . . . H8 H 0.6241 0.6402 0.7163 0.045 Uiso 1 1 calc R . . C9 C 0.8238(7) 0.66851(15) 0.7033(7) 0.0392(16) Uani 1 1 d . . . H9 H 0.8880 0.6596 0.7886 0.047 Uiso 1 1 calc R . . C10 C 0.8885(7) 0.69256(15) 0.6217(7) 0.0370(16) Uani 1 1 d . . . H10 H 0.9953 0.7002 0.6484 0.044 Uiso 1 1 calc R . . C11 C 0.7866(7) 0.70484(14) 0.4975(6) 0.0268(13) Uani 1 1 d . . . C12 C 0.7716(7) 0.74154(14) 0.2645(7) 0.0399(16) Uani 1 1 d . . . H12 H 0.6696 0.7356 0.2142 0.048 Uiso 1 1 calc R . . C13 C 0.8736(8) 0.76370(16) 0.2123(8) 0.0501(19) Uani 1 1 d . . . H13 H 0.8586 0.7758 0.1188 0.060 Uiso 1 1 calc R . . C14 C 1.0072(9) 0.76435(17) 0.3306(8) 0.055(2) Uani 1 1 d . . . H14 H 1.0968 0.7778 0.3281 0.066 Uiso 1 1 calc R . . C15 C 0.2995(7) 0.67251(14) 0.3589(6) 0.0296(14) Uani 1 1 d . . . C16 C 0.3362(9) 0.69641(16) 0.2542(8) 0.058(2) Uani 1 1 d . . . H16 H 0.4398 0.7063 0.2629 0.069 Uiso 1 1 calc R . . C17 C 0.2138(9) 0.70509(17) 0.1366(8) 0.060(2) Uani 1 1 d . . . H17 H 0.2350 0.7213 0.0676 0.071 Uiso 1 1 calc R . . C18 C 0.0640(7) 0.69041(14) 0.1201(7) 0.0386(16) Uani 1 1 d . . . H18 H -0.0183 0.6960 0.0410 0.046 Uiso 1 1 calc R . . C19 C 0.0404(7) 0.66656(13) 0.2278(6) 0.0284(14) Uani 1 1 d . . . C20 C -0.1400(9) 0.62346(17) 0.2947(8) 0.0522(19) Uani 1 1 d . . . H20 H -0.0693 0.6138 0.3724 0.063 Uiso 1 1 calc R . . C21 C -0.2947(9) 0.6141(2) 0.2395(9) 0.069(2) Uani 1 1 d . . . H21 H -0.3527 0.5970 0.2721 0.082 Uiso 1 1 calc R . . C22 C -0.3474(9) 0.6351(2) 0.1251(8) 0.066(3) Uani 1 1 d . . . H22 H -0.4497 0.6340 0.0652 0.079 Uiso 1 1 calc R . . C23 C 0.4413(7) 0.54879(13) 1.1851(6) 0.0292(14) Uani 1 1 d . . . H23 H 0.5583 0.5467 1.1820 0.035 Uiso 1 1 calc R . . C24 C 0.3586(7) 0.56192(13) 1.0499(6) 0.0296(14) Uani 1 1 d . . . H24 H 0.4198 0.5686 0.9599 0.036 Uiso 1 1 calc R . . C25 C 0.1844(7) 0.56511(12) 1.0488(6) 0.0253(13) Uani 1 1 d . . . C26 C 0.1009(7) 0.55588(12) 1.1917(6) 0.0241(13) Uani 1 1 d . . . H26 H -0.0155 0.5584 1.1995 0.029 Uiso 1 1 calc R . . C27 C 0.1943(7) 0.54309(13) 1.3200(6) 0.0279(14) Uani 1 1 d . . . H27 H 0.1369 0.5369 1.4135 0.034 Uiso 1 1 calc R . . C28 C -0.2678(7) 0.52582(14) 0.8270(6) 0.0325(15) Uani 1 1 d . . . H28 H -0.3173 0.5094 0.8772 0.039 Uiso 1 1 calc R . . C29 C -0.1266(7) 0.53746(14) 0.9044(6) 0.0308(14) Uani 1 1 d . . . H29 H -0.0777 0.5280 0.9972 0.037 Uiso 1 1 calc R . . C30 C -0.0560(7) 0.56397(13) 0.8418(6) 0.0256(13) Uani 1 1 d . . . C31 C -0.1398(7) 0.57608(14) 0.7021(7) 0.0390(16) Uani 1 1 d . . . H31 H -0.1041 0.5942 0.6582 0.047 Uiso 1 1 calc R . . C32 C -0.2749(8) 0.56126(16) 0.6293(7) 0.0455(18) Uani 1 1 d . . . H32 H -0.3237 0.5696 0.5332 0.055 Uiso 1 1 calc R . . 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 Cd1 0.0231(3) 0.0307(3) 0.0225(3) 0.0059(3) -0.0009(2) -0.0034(3) Br1 0.0341(4) 0.0463(4) 0.0382(3) 0.0164(3) 0.0111(3) 0.0034(4) N1 0.026(3) 0.022(3) 0.035(3) 0.012(2) 0.0000(19) -0.005(2) N2 0.026(3) 0.027(3) 0.028(2) 0.007(2) -0.0045(19) -0.007(2) N3 0.024(3) 0.024(3) 0.028(2) 0.003(2) 0.0050(19) -0.005(2) N4 0.031(3) 0.031(3) 0.034(3) 0.003(2) 0.003(2) -0.014(3) N5 0.039(3) 0.051(4) 0.052(3) 0.006(3) 0.000(2) -0.025(3) N6 0.026(3) 0.030(3) 0.029(2) 0.002(2) 0.002(2) 0.000(3) N7 0.032(3) 0.038(3) 0.034(3) -0.003(3) -0.005(2) -0.005(3) N8 0.047(4) 0.079(5) 0.046(3) 0.006(3) -0.017(3) -0.014(4) N9 0.032(3) 0.029(3) 0.020(2) 0.009(2) -0.0033(19) -0.009(3) N10 0.033(3) 0.038(3) 0.039(3) 0.005(3) -0.006(2) -0.014(3) C1 0.023(3) 0.026(3) 0.033(3) 0.013(3) 0.001(2) -0.003(3) C2 0.034(3) 0.020(3) 0.037(3) 0.005(3) 0.003(3) 0.000(3) C3 0.038(4) 0.023(3) 0.028(3) 0.004(3) 0.003(2) -0.002(3) C4 0.018(3) 0.019(3) 0.030(3) 0.008(3) -0.001(2) 0.000(3) C5 0.044(4) 0.023(3) 0.028(3) -0.002(3) -0.002(3) -0.007(3) C6 0.041(4) 0.032(4) 0.026(3) -0.003(3) 0.007(2) 0.004(3) C7 0.023(3) 0.025(3) 0.025(3) 0.002(3) 0.003(2) 0.001(3) C8 0.038(4) 0.036(4) 0.038(3) 0.014(3) 0.002(3) -0.008(3) C9 0.030(4) 0.048(4) 0.039(3) 0.012(3) -0.007(3) 0.003(4) C10 0.024(3) 0.046(4) 0.041(4) -0.001(3) 0.001(3) -0.008(3) C11 0.023(3) 0.032(4) 0.025(3) -0.001(3) 0.004(2) -0.007(3) C12 0.039(4) 0.041(4) 0.039(3) 0.009(3) -0.001(3) -0.008(4) C13 0.048(4) 0.044(5) 0.058(4) 0.022(4) 0.001(3) -0.013(4) C14 0.045(5) 0.048(5) 0.073(5) 0.002(4) 0.016(4) -0.022(4) C15 0.030(3) 0.032(4) 0.026(3) 0.003(3) 0.001(2) -0.002(3) C16 0.045(4) 0.055(5) 0.073(5) 0.035(4) -0.018(3) -0.022(4) C17 0.067(5) 0.051(5) 0.059(4) 0.036(4) -0.023(4) -0.016(4) C18 0.034(4) 0.037(4) 0.044(4) 0.005(3) -0.005(3) -0.002(3) C19 0.029(3) 0.031(4) 0.025(3) -0.003(3) 0.003(2) -0.004(3) C20 0.049(5) 0.046(5) 0.061(4) 0.014(4) -0.011(3) -0.013(4) C21 0.064(6) 0.082(7) 0.059(5) 0.003(5) -0.007(4) -0.038(5) C22 0.038(4) 0.109(8) 0.051(4) -0.004(5) -0.009(3) -0.023(5) C23 0.025(3) 0.024(3) 0.038(3) 0.008(3) -0.004(2) 0.001(3) C24 0.031(3) 0.030(4) 0.028(3) 0.011(3) 0.002(2) -0.008(3) C25 0.034(3) 0.019(3) 0.022(3) 0.003(2) -0.003(2) -0.004(3) C26 0.024(3) 0.021(3) 0.028(3) 0.004(3) 0.003(2) -0.003(3) C27 0.039(4) 0.021(3) 0.023(3) 0.005(3) 0.002(2) -0.005(3) C28 0.036(4) 0.036(4) 0.025(3) 0.006(3) 0.002(3) -0.002(3) C29 0.032(3) 0.036(4) 0.024(3) 0.006(3) -0.007(2) -0.003(3) C30 0.028(3) 0.027(3) 0.022(3) -0.003(3) 0.001(2) -0.008(3) C31 0.040(4) 0.034(4) 0.042(3) 0.019(3) -0.012(3) -0.011(3) C32 0.041(4) 0.051(5) 0.043(4) 0.016(3) -0.016(3) -0.004(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 Cd1 N9 2.487(4) . ? Cd1 N9 2.487(4) 3_668 ? Cd1 N10 2.496(5) 3_567 ? Cd1 N10 2.496(5) 1_656 ? Cd1 Br1 2.6646(6) 3_668 ? Cd1 Br1 2.6646(6) . ? N1 C7 1.400(7) . ? N1 C15 1.423(7) . ? N1 C1 1.468(6) . ? N2 C30 1.397(6) . ? N2 C25 1.421(6) . ? N2 C4 1.459(6) . ? N3 C11 1.326(6) . ? N3 C7 1.352(7) . ? N4 N5 1.345(6) . ? N4 C12 1.355(7) . ? N4 C11 1.422(7) . ? N5 C14 1.329(8) . ? N6 C19 1.328(6) . ? N6 C15 1.344(7) . ? N7 C20 1.348(8) . ? N7 N8 1.363(7) . ? N7 C19 1.402(7) . ? N8 C22 1.317(9) . ? N9 C23 1.334(6) . ? N9 C27 1.350(7) . ? N10 C32 1.336(8) . ? N10 C28 1.339(7) . ? N10 Cd1 2.496(5) 1_454 ? C1 C6 1.367(8) . ? C1 C2 1.381(7) . ? C2 C3 1.374(7) . ? C2 H2 0.9300 . ? C3 C4 1.375(8) . ? C3 H3 0.9300 . ? C4 C5 1.381(7) . ? C5 C6 1.392(7) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.408(7) . ? C8 C9 1.382(8) . ? C8 H8 0.9300 . ? C9 C10 1.364(8) . ? C9 H9 0.9300 . ? C10 C11 1.378(7) . ? C10 H10 0.9300 . ? C12 C13 1.350(8) . ? C12 H12 0.9300 . ? C13 C14 1.400(9) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.394(8) . ? C16 C17 1.387(8) . ? C16 H16 0.9300 . ? C17 C18 1.356(8) . ? C17 H17 0.9300 . ? C18 C19 1.387(8) . ? C18 H18 0.9300 . ? C20 C21 1.355(9) . ? C20 H20 0.9300 . ? C21 C22 1.371(10) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.382(7) . ? C23 H23 0.9300 . ? C24 C25 1.383(7) . ? C24 H24 0.9300 . ? C25 C26 1.402(7) . ? C26 C27 1.374(7) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 C29 1.364(7) . ? C28 H28 0.9300 . ? C29 C30 1.407(8) . ? C29 H29 0.9300 . ? C30 C31 1.396(7) . ? C31 C32 1.371(8) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? 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 N9 Cd1 N9 180.00(16) . 3_668 ? N9 Cd1 N10 84.18(15) . 3_567 ? N9 Cd1 N10 95.82(15) 3_668 3_567 ? N9 Cd1 N10 95.82(15) . 1_656 ? N9 Cd1 N10 84.18(15) 3_668 1_656 ? N10 Cd1 N10 180.00(19) 3_567 1_656 ? N9 Cd1 Br1 89.75(10) . 3_668 ? N9 Cd1 Br1 90.25(10) 3_668 3_668 ? N10 Cd1 Br1 90.84(11) 3_567 3_668 ? N10 Cd1 Br1 89.16(11) 1_656 3_668 ? N9 Cd1 Br1 90.25(10) . . ? N9 Cd1 Br1 89.75(10) 3_668 . ? N10 Cd1 Br1 89.16(11) 3_567 . ? N10 Cd1 Br1 90.84(11) 1_656 . ? Br1 Cd1 Br1 180.0 3_668 . ? C7 N1 C15 127.5(4) . . ? C7 N1 C1 116.3(4) . . ? C15 N1 C1 116.2(4) . . ? C30 N2 C25 124.0(4) . . ? C30 N2 C4 118.0(4) . . ? C25 N2 C4 116.6(4) . . ? C11 N3 C7 117.9(5) . . ? N5 N4 C12 112.1(5) . . ? N5 N4 C11 120.7(5) . . ? C12 N4 C11 127.1(5) . . ? C14 N5 N4 103.9(5) . . ? C19 N6 C15 118.0(5) . . ? C20 N7 N8 111.6(6) . . ? C20 N7 C19 127.1(5) . . ? N8 N7 C19 121.3(5) . . ? C22 N8 N7 103.4(6) . . ? C23 N9 C27 115.8(4) . . ? C23 N9 Cd1 120.0(4) . . ? C27 N9 Cd1 120.5(3) . . ? C32 N10 C28 113.7(5) . . ? C32 N10 Cd1 122.6(4) . 1_454 ? C28 N10 Cd1 119.5(4) . 1_454 ? C6 C1 C2 120.5(5) . . ? C6 C1 N1 120.5(5) . . ? C2 C1 N1 119.0(5) . . ? C3 C2 C1 119.5(6) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 120.3(5) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 120.5(5) . . ? C3 C4 N2 119.5(5) . . ? C5 C4 N2 119.9(5) . . ? C4 C5 C6 118.9(5) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C1 C6 C5 120.2(5) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? N3 C7 N1 117.9(5) . . ? N3 C7 C8 121.1(5) . . ? N1 C7 C8 120.9(5) . . ? C9 C8 C7 117.6(5) . . ? C9 C8 H8 121.2 . . ? C7 C8 H8 121.2 . . ? C10 C9 C8 121.8(6) . . ? C10 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? C9 C10 C11 116.2(6) . . ? C9 C10 H10 121.9 . . ? C11 C10 H10 121.9 . . ? N3 C11 C10 125.3(5) . . ? N3 C11 N4 114.7(5) . . ? C10 C11 N4 120.0(5) . . ? C13 C12 N4 107.4(6) . . ? C13 C12 H12 126.3 . . ? N4 C12 H12 126.3 . . ? C12 C13 C14 104.4(6) . . ? C12 C13 H13 127.8 . . ? C14 C13 H13 127.8 . . ? N5 C14 C13 112.2(6) . . ? N5 C14 H14 123.9 . . ? C13 C14 H14 123.9 . . ? N6 C15 C16 121.4(5) . . ? N6 C15 N1 113.1(5) . . ? C16 C15 N1 125.4(6) . . ? C17 C16 C15 118.1(6) . . ? C17 C16 H16 120.9 . . ? C15 C16 H16 120.9 . . ? C18 C17 C16 121.4(6) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C17 C18 C19 116.2(6) . . ? C17 C18 H18 121.9 . . ? C19 C18 H18 121.9 . . ? N6 C19 C18 124.8(6) . . ? N6 C19 N7 115.0(5) . . ? C18 C19 N7 120.1(5) . . ? N7 C20 C21 106.8(7) . . ? N7 C20 H20 126.6 . . ? C21 C20 H20 126.6 . . ? C20 C21 C22 105.1(7) . . ? C20 C21 H21 127.4 . . ? C22 C21 H21 127.4 . . ? N8 C22 C21 113.0(6) . . ? N8 C22 H22 123.5 . . ? C21 C22 H22 123.5 . . ? N9 C23 C24 124.0(5) . . ? N9 C23 H23 118.0 . . ? C24 C23 H23 118.0 . . ? C23 C24 C25 119.8(5) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C24 C25 C26 117.1(5) . . ? C24 C25 N2 121.3(4) . . ? C26 C25 N2 121.5(5) . . ? C27 C26 C25 118.7(5) . . ? C27 C26 H26 120.6 . . ? C25 C26 H26 120.6 . . ? N9 C27 C26 124.5(5) . . ? N9 C27 H27 117.7 . . ? C26 C27 H27 117.7 . . ? N10 C28 C29 126.3(6) . . ? N10 C28 H28 116.9 . . ? C29 C28 H28 116.9 . . ? C28 C29 C30 119.0(5) . . ? C28 C29 H29 120.5 . . ? C30 C29 H29 120.5 . . ? C31 C30 N2 121.6(5) . . ? C31 C30 C29 115.4(5) . . ? N2 C30 C29 122.9(5) . . ? C32 C31 C30 120.1(5) . . ? C32 C31 H31 120.0 . . ? C30 C31 H31 120.0 . . ? N10 C32 C31 125.2(6) . . ? N10 C32 H32 117.4 . . ? C31 C32 H32 117.4 . . ? 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 C12 N4 N5 C14 -0.2(7) . . . . ? C11 N4 N5 C14 178.2(5) . . . . ? C20 N7 N8 C22 -0.5(7) . . . . ? C19 N7 N8 C22 176.3(5) . . . . ? N9 Cd1 N9 C23 0(100) 3_668 . . . ? N10 Cd1 N9 C23 -90.8(4) 3_567 . . . ? N10 Cd1 N9 C23 89.2(4) 1_656 . . . ? Br1 Cd1 N9 C23 0.1(4) 3_668 . . . ? Br1 Cd1 N9 C23 -179.9(4) . . . . ? N9 Cd1 N9 C27 0(100) 3_668 . . . ? N10 Cd1 N9 C27 66.8(4) 3_567 . . . ? N10 Cd1 N9 C27 -113.2(4) 1_656 . . . ? Br1 Cd1 N9 C27 157.6(4) 3_668 . . . ? Br1 Cd1 N9 C27 -22.4(4) . . . . ? C7 N1 C1 C6 -102.7(6) . . . . ? C15 N1 C1 C6 79.5(7) . . . . ? C7 N1 C1 C2 76.7(6) . . . . ? C15 N1 C1 C2 -101.2(6) . . . . ? C6 C1 C2 C3 -3.1(9) . . . . ? N1 C1 C2 C3 177.6(5) . . . . ? C1 C2 C3 C4 0.9(9) . . . . ? C2 C3 C4 C5 2.0(9) . . . . ? C2 C3 C4 N2 -176.2(5) . . . . ? C30 N2 C4 C3 113.9(6) . . . . ? C25 N2 C4 C3 -79.4(7) . . . . ? C30 N2 C4 C5 -64.3(7) . . . . ? C25 N2 C4 C5 102.4(6) . . . . ? C3 C4 C5 C6 -2.7(8) . . . . ? N2 C4 C5 C6 175.5(5) . . . . ? C2 C1 C6 C5 2.4(9) . . . . ? N1 C1 C6 C5 -178.3(5) . . . . ? C4 C5 C6 C1 0.6(9) . . . . ? C11 N3 C7 N1 179.3(5) . . . . ? C11 N3 C7 C8 -0.6(8) . . . . ? C15 N1 C7 N3 6.9(8) . . . . ? C1 N1 C7 N3 -170.6(5) . . . . ? C15 N1 C7 C8 -173.1(5) . . . . ? C1 N1 C7 C8 9.3(7) . . . . ? N3 C7 C8 C9 2.3(8) . . . . ? N1 C7 C8 C9 -177.6(5) . . . . ? C7 C8 C9 C10 -2.2(9) . . . . ? C8 C9 C10 C11 0.5(9) . . . . ? C7 N3 C11 C10 -1.4(8) . . . . ? C7 N3 C11 N4 178.8(4) . . . . ? C9 C10 C11 N3 1.5(9) . . . . ? C9 C10 C11 N4 -178.7(5) . . . . ? N5 N4 C11 N3 172.1(5) . . . . ? C12 N4 C11 N3 -9.8(8) . . . . ? N5 N4 C11 C10 -7.7(8) . . . . ? C12 N4 C11 C10 170.4(6) . . . . ? N5 N4 C12 C13 1.1(7) . . . . ? C11 N4 C12 C13 -177.2(5) . . . . ? N4 C12 C13 C14 -1.4(8) . . . . ? N4 N5 C14 C13 -0.7(8) . . . . ? C12 C13 C14 N5 1.4(9) . . . . ? C19 N6 C15 C16 0.7(8) . . . . ? C19 N6 C15 N1 177.6(5) . . . . ? C7 N1 C15 N6 177.3(5) . . . . ? C1 N1 C15 N6 -5.1(7) . . . . ? C7 N1 C15 C16 -5.9(10) . . . . ? C1 N1 C15 C16 171.6(6) . . . . ? N6 C15 C16 C17 1.1(10) . . . . ? N1 C15 C16 C17 -175.4(6) . . . . ? C15 C16 C17 C18 -1.6(12) . . . . ? C16 C17 C18 C19 0.4(11) . . . . ? C15 N6 C19 C18 -2.1(8) . . . . ? C15 N6 C19 N7 177.1(5) . . . . ? C17 C18 C19 N6 1.5(9) . . . . ? C17 C18 C19 N7 -177.6(6) . . . . ? C20 N7 C19 N6 -8.7(8) . . . . ? N8 N7 C19 N6 175.0(5) . . . . ? C20 N7 C19 C18 170.5(6) . . . . ? N8 N7 C19 C18 -5.8(8) . . . . ? N8 N7 C20 C21 -0.3(8) . . . . ? C19 N7 C20 C21 -176.9(6) . . . . ? N7 C20 C21 C22 1.0(9) . . . . ? N7 N8 C22 C21 1.2(9) . . . . ? C20 C21 C22 N8 -1.4(10) . . . . ? C27 N9 C23 C24 -1.5(8) . . . . ? Cd1 N9 C23 C24 157.1(4) . . . . ? N9 C23 C24 C25 -0.8(9) . . . . ? C23 C24 C25 C26 3.0(8) . . . . ? C23 C24 C25 N2 -175.3(5) . . . . ? C30 N2 C25 C24 135.3(6) . . . . ? C4 N2 C25 C24 -30.5(8) . . . . ? C30 N2 C25 C26 -42.9(8) . . . . ? C4 N2 C25 C26 151.3(5) . . . . ? C24 C25 C26 C27 -2.9(8) . . . . ? N2 C25 C26 C27 175.4(5) . . . . ? C23 N9 C27 C26 1.5(8) . . . . ? Cd1 N9 C27 C26 -157.0(4) . . . . ? C25 C26 C27 N9 0.7(9) . . . . ? C32 N10 C28 C29 -6.5(9) . . . . ? Cd1 N10 C28 C29 151.0(5) 1_454 . . . ? N10 C28 C29 C30 5.7(9) . . . . ? C25 N2 C30 C31 179.9(5) . . . . ? C4 N2 C30 C31 -14.5(8) . . . . ? C25 N2 C30 C29 -4.4(8) . . . . ? C4 N2 C30 C29 161.2(5) . . . . ? C28 C29 C30 C31 -0.1(8) . . . . ? C28 C29 C30 N2 -176.1(5) . . . . ? N2 C30 C31 C32 172.1(6) . . . . ? C29 C30 C31 C32 -3.9(9) . . . . ? C28 N10 C32 C31 1.9(9) . . . . ? Cd1 N10 C32 C31 -154.7(5) 1_454 . . . ? C30 C31 C32 N10 3.1(10) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.392 _refine_diff_density_min -0.570 _refine_diff_density_rms 0.096 _database_code_depnum_ccdc_archive 'CCDC 968022' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_111220g _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H24 Cd I2 N10' _chemical_formula_weight 914.81 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 10.8437(11) _cell_length_b 16.6662(16) _cell_length_c 19.6797(18) _cell_angle_alpha 90.00 _cell_angle_beta 96.6390(10) _cell_angle_gamma 90.00 _cell_volume 3532.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5174 _cell_measurement_theta_min 2.252 _cell_measurement_theta_max 23.27 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.720 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 2.403 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4466 _exptl_absorpt_correction_T_max 0.5326 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17488 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 25.02 _reflns_number_total 6222 _reflns_number_gt 4011 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.0669P)^2^+2.8394P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6222 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0815 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1444 _refine_ls_wR_factor_gt 0.1309 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 Cd1 Cd 0.41985(4) 0.32294(3) 0.80696(3) 0.04983(18) Uani 1 1 d . . . I1 I 0.39228(5) 0.40128(3) 0.92457(3) 0.0720(2) Uani 1 1 d . . . I2 I 0.25703(7) 0.22707(5) 0.73426(4) 0.1134(3) Uani 1 1 d . . . N1 N 0.2306(5) 0.6957(3) 0.3970(3) 0.0447(14) Uani 1 1 d . . . N2 N 0.5677(4) 0.6295(3) 0.6306(2) 0.0395(12) Uani 1 1 d . . . N3 N 0.1542(5) 0.5685(3) 0.4150(3) 0.0446(13) Uani 1 1 d . . . N4 N 0.0877(5) 0.4425(4) 0.4434(4) 0.0567(16) Uani 1 1 d . . . N5 N 0.0145(6) 0.3760(4) 0.4314(4) 0.076(2) Uani 1 1 d . . . N6 N 0.2846(5) 0.8283(4) 0.3904(3) 0.0451(14) Uani 1 1 d . . . N7 N 0.3561(6) 0.9595(4) 0.3921(3) 0.0639(17) Uani 1 1 d . . . N8 N 0.3371(8) 1.0399(5) 0.3861(4) 0.090(2) Uani 1 1 d . . . N9 N 0.4741(5) 0.4226(3) 0.7351(3) 0.0449(13) Uani 1 1 d . . . N10 N 0.8870(5) 0.7686(3) 0.6785(3) 0.0438(13) Uani 1 1 d . . . C1 C 0.3199(5) 0.6818(4) 0.4560(3) 0.0381(14) Uani 1 1 d . . . C2 C 0.4144(6) 0.6269(4) 0.4529(3) 0.0446(16) Uani 1 1 d . . . H2 H 0.4227 0.6006 0.4120 0.054 Uiso 1 1 calc R . . C3 C 0.4966(6) 0.6107(4) 0.5102(3) 0.0410(15) Uani 1 1 d . . . H3 H 0.5599 0.5734 0.5082 0.049 Uiso 1 1 calc R . . C4 C 0.4841(5) 0.6502(4) 0.5700(3) 0.0343(14) Uani 1 1 d . . . C5 C 0.3941(6) 0.7065(4) 0.5736(3) 0.0429(16) Uani 1 1 d . . . H5 H 0.3879 0.7340 0.6141 0.051 Uiso 1 1 calc R . . C6 C 0.3122(6) 0.7222(4) 0.5161(3) 0.0438(16) Uani 1 1 d . . . H6 H 0.2508 0.7608 0.5182 0.053 Uiso 1 1 calc R . . C7 C 0.1561(6) 0.6298(4) 0.3726(3) 0.0457(16) Uani 1 1 d . . . C8 C 0.0915(7) 0.6289(5) 0.3073(4) 0.064(2) Uani 1 1 d . . . H8 H 0.0950 0.6721 0.2777 0.077 Uiso 1 1 calc R . . C9 C 0.0226(7) 0.5622(6) 0.2882(4) 0.069(2) Uani 1 1 d . . . H9 H -0.0218 0.5603 0.2449 0.083 Uiso 1 1 calc R . . C10 C 0.0174(7) 0.4980(6) 0.3315(5) 0.069(2) Uani 1 1 d . . . H10 H -0.0289 0.4523 0.3187 0.083 Uiso 1 1 calc R . . C11 C 0.0844(6) 0.5051(5) 0.3946(4) 0.0546(19) Uani 1 1 d . . . C12 C 0.0400(10) 0.3354(6) 0.4895(6) 0.086(3) Uani 1 1 d . . . H12 H 0.0023 0.2867 0.4975 0.103 Uiso 1 1 calc R . . C13 C 0.1259(8) 0.3707(6) 0.5364(5) 0.073(2) Uani 1 1 d . . . H13 H 0.1579 0.3513 0.5791 0.087 Uiso 1 1 calc R . . C14 C 0.1537(7) 0.4404(5) 0.5063(5) 0.065(2) Uani 1 1 d . . . H14 H 0.2081 0.4797 0.5253 0.078 Uiso 1 1 calc R . . C15 C 0.1926(6) 0.7762(4) 0.3849(3) 0.0423(16) Uani 1 1 d . . . C16 C 0.0685(6) 0.7989(5) 0.3721(3) 0.0531(18) Uani 1 1 d . . . H16 H 0.0055 0.7607 0.3674 0.064 Uiso 1 1 calc R . . C17 C 0.0415(7) 0.8794(5) 0.3667(4) 0.0570(19) Uani 1 1 d . . . H17 H -0.0406 0.8963 0.3582 0.068 Uiso 1 1 calc R . . C18 C 0.1355(7) 0.9349(5) 0.3737(3) 0.0559(19) Uani 1 1 d . . . H18 H 0.1193 0.9896 0.3706 0.067 Uiso 1 1 calc R . . C19 C 0.2543(7) 0.9059(4) 0.3857(3) 0.0502(17) Uani 1 1 d . . . C20 C 0.4479(14) 1.0691(8) 0.3966(6) 0.108(4) Uani 1 1 d . . . H20 H 0.4644 1.1238 0.3964 0.130 Uiso 1 1 calc R . . C21 C 0.5383(12) 1.0126(9) 0.4079(6) 0.115(4) Uani 1 1 d . . . H21 H 0.6238 1.0202 0.4153 0.138 Uiso 1 1 calc R . . C22 C 0.4742(10) 0.9421(7) 0.4058(6) 0.098(3) Uani 1 1 d . . . H22 H 0.5080 0.8911 0.4129 0.118 Uiso 1 1 calc R . . C23 C 0.3889(6) 0.4694(5) 0.7020(4) 0.059(2) Uani 1 1 d . . . H23 H 0.3060 0.4551 0.7021 0.071 Uiso 1 1 calc R . . C24 C 0.4149(6) 0.5381(5) 0.6671(4) 0.057(2) Uani 1 1 d . . . H24 H 0.3511 0.5688 0.6446 0.069 Uiso 1 1 calc R . . C25 C 0.5389(5) 0.5609(4) 0.6662(3) 0.0361(14) Uani 1 1 d . . . C26 C 0.6285(6) 0.5090(4) 0.6991(3) 0.0377(14) Uani 1 1 d . . . H26 H 0.7125 0.5199 0.6984 0.045 Uiso 1 1 calc R . . C27 C 0.5925(5) 0.4427(4) 0.7321(3) 0.0376(14) Uani 1 1 d . . . H27 H 0.6539 0.4096 0.7537 0.045 Uiso 1 1 calc R . . C28 C 0.8178(6) 0.7737(4) 0.6191(3) 0.0467(17) Uani 1 1 d . . . H28 H 0.8417 0.8099 0.5871 0.056 Uiso 1 1 calc R . . C29 C 0.7127(6) 0.7290(4) 0.6012(3) 0.0459(17) Uani 1 1 d . . . H29 H 0.6687 0.7342 0.5580 0.055 Uiso 1 1 calc R . . C30 C 0.6730(5) 0.6763(4) 0.6482(3) 0.0348(14) Uani 1 1 d . . . C31 C 0.7403(6) 0.6737(4) 0.7129(3) 0.0444(16) Uani 1 1 d . . . H31 H 0.7146 0.6414 0.7471 0.053 Uiso 1 1 calc R . . C32 C 0.8461(6) 0.7201(4) 0.7252(3) 0.0475(17) Uani 1 1 d . . . H32 H 0.8914 0.7174 0.7683 0.057 Uiso 1 1 calc R . . 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 Cd1 0.0388(3) 0.0482(3) 0.0620(4) 0.0164(3) 0.0036(2) 0.0013(2) I1 0.0800(4) 0.0563(4) 0.0859(4) 0.0037(3) 0.0369(3) 0.0053(3) I2 0.0966(5) 0.1299(7) 0.1031(6) 0.0134(5) -0.0336(4) -0.0536(5) N1 0.042(3) 0.041(3) 0.046(3) 0.003(3) -0.017(2) 0.002(2) N2 0.037(3) 0.039(3) 0.039(3) 0.003(3) -0.006(2) -0.010(2) N3 0.045(3) 0.038(3) 0.050(3) -0.010(3) 0.001(3) -0.001(2) N4 0.050(4) 0.040(4) 0.083(5) -0.008(3) 0.020(3) -0.008(3) N5 0.070(5) 0.058(5) 0.104(6) -0.026(5) 0.024(4) -0.020(4) N6 0.042(3) 0.055(4) 0.036(3) 0.006(3) -0.005(2) -0.002(3) N7 0.070(5) 0.052(5) 0.068(4) 0.002(3) -0.001(3) -0.017(3) N8 0.109(6) 0.051(5) 0.111(6) -0.001(4) 0.021(5) -0.025(4) N9 0.041(3) 0.047(4) 0.045(3) 0.010(3) -0.003(2) 0.000(3) N10 0.042(3) 0.041(3) 0.047(3) -0.003(3) 0.001(3) -0.006(2) C1 0.035(3) 0.038(4) 0.038(3) 0.001(3) -0.006(3) 0.000(3) C2 0.041(4) 0.049(4) 0.042(4) -0.010(3) -0.005(3) 0.002(3) C3 0.039(4) 0.035(4) 0.047(4) -0.003(3) -0.003(3) 0.006(3) C4 0.036(3) 0.032(4) 0.034(3) 0.001(3) -0.002(3) -0.005(3) C5 0.052(4) 0.036(4) 0.040(4) -0.012(3) 0.000(3) 0.002(3) C6 0.045(4) 0.043(4) 0.042(4) -0.002(3) 0.000(3) 0.017(3) C7 0.039(4) 0.046(4) 0.050(4) -0.010(3) -0.006(3) -0.001(3) C8 0.059(5) 0.068(6) 0.060(5) -0.008(4) -0.015(4) -0.003(4) C9 0.054(5) 0.084(7) 0.064(5) -0.026(5) -0.021(4) -0.010(4) C10 0.051(5) 0.068(6) 0.086(6) -0.029(5) -0.002(4) -0.012(4) C11 0.041(4) 0.055(5) 0.068(5) -0.023(4) 0.005(4) -0.003(3) C12 0.104(8) 0.063(6) 0.101(8) 0.008(6) 0.055(7) -0.004(6) C13 0.076(6) 0.066(6) 0.080(6) 0.002(5) 0.020(5) -0.008(5) C14 0.055(5) 0.052(5) 0.087(6) -0.011(5) 0.005(4) -0.005(4) C15 0.044(4) 0.043(4) 0.038(4) 0.008(3) -0.003(3) 0.002(3) C16 0.045(4) 0.061(5) 0.051(4) 0.007(4) -0.004(3) 0.003(3) C17 0.054(4) 0.058(5) 0.057(5) 0.013(4) -0.003(4) 0.008(4) C18 0.074(5) 0.048(5) 0.046(4) 0.011(3) 0.008(4) 0.011(4) C19 0.069(5) 0.042(5) 0.039(4) 0.000(3) 0.004(3) -0.002(4) C20 0.136(11) 0.084(9) 0.103(9) -0.009(7) 0.007(8) -0.037(8) C21 0.086(8) 0.123(11) 0.133(10) 0.012(9) -0.002(7) -0.058(8) C22 0.083(7) 0.079(7) 0.128(9) 0.015(7) -0.010(6) -0.027(6) C23 0.034(4) 0.062(5) 0.079(5) 0.035(4) -0.005(3) -0.012(3) C24 0.041(4) 0.056(5) 0.072(5) 0.023(4) -0.007(3) -0.004(3) C25 0.037(3) 0.037(4) 0.032(3) -0.003(3) -0.005(3) -0.004(3) C26 0.037(3) 0.037(4) 0.039(3) -0.004(3) 0.001(3) -0.003(3) C27 0.036(4) 0.036(4) 0.040(4) 0.007(3) 0.001(3) 0.000(3) C28 0.043(4) 0.050(5) 0.045(4) 0.004(3) 0.000(3) -0.017(3) C29 0.047(4) 0.052(5) 0.036(4) 0.002(3) -0.007(3) -0.014(3) C30 0.037(3) 0.031(4) 0.035(3) -0.003(3) -0.001(3) -0.001(3) C31 0.052(4) 0.043(4) 0.035(4) 0.001(3) -0.005(3) -0.016(3) C32 0.053(4) 0.048(5) 0.038(4) -0.006(3) -0.010(3) -0.001(3) _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 Cd1 N10 2.270(5) 2_646 ? Cd1 N9 2.301(5) . ? Cd1 I2 2.6708(9) . ? Cd1 I1 2.7038(8) . ? N1 C7 1.414(8) . ? N1 C15 1.414(8) . ? N1 C1 1.442(8) . ? N2 C30 1.393(7) . ? N2 C25 1.395(8) . ? N2 C4 1.454(7) . ? N3 C7 1.321(9) . ? N3 C11 1.334(9) . ? N4 C14 1.357(10) . ? N4 N5 1.367(8) . ? N4 C11 1.416(10) . ? N5 C12 1.329(12) . ? N6 C15 1.317(8) . ? N6 C19 1.335(9) . ? N7 C22 1.311(12) . ? N7 N8 1.358(10) . ? N7 C19 1.415(9) . ? N8 C20 1.291(14) . ? N9 C23 1.323(8) . ? N9 C27 1.335(7) . ? N10 C28 1.318(8) . ? N10 C32 1.337(9) . ? N10 Cd1 2.270(5) 2_656 ? C1 C6 1.372(9) . ? C1 C2 1.381(9) . ? C2 C3 1.381(9) . ? C2 H2 0.9300 . ? C3 C4 1.369(8) . ? C3 H3 0.9300 . ? C4 C5 1.362(9) . ? C5 C6 1.379(9) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.390(10) . ? C8 C9 1.367(11) . ? C8 H8 0.9300 . ? C9 C10 1.373(12) . ? C9 H9 0.9300 . ? C10 C11 1.369(11) . ? C10 H10 0.9300 . ? C12 C13 1.366(13) . ? C12 H12 0.9300 . ? C13 C14 1.354(12) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.393(9) . ? C16 C17 1.374(10) . ? C16 H16 0.9300 . ? C17 C18 1.370(11) . ? C17 H17 0.9300 . ? C18 C19 1.370(10) . ? C18 H18 0.9300 . ? C20 C21 1.359(16) . ? C20 H20 0.9300 . ? C21 C22 1.364(14) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.381(9) . ? C23 H23 0.9300 . ? C24 C25 1.399(9) . ? C24 H24 0.9300 . ? C25 C26 1.402(9) . ? C26 C27 1.361(9) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 C29 1.372(9) . ? C28 H28 0.9300 . ? C29 C30 1.380(9) . ? C29 H29 0.9300 . ? C30 C31 1.392(8) . ? C31 C32 1.381(9) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? 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 N10 Cd1 N9 93.87(19) 2_646 . ? N10 Cd1 I2 111.83(15) 2_646 . ? N9 Cd1 I2 107.62(14) . . ? N10 Cd1 I1 106.08(14) 2_646 . ? N9 Cd1 I1 103.82(14) . . ? I2 Cd1 I1 128.01(3) . . ? C7 N1 C15 122.3(5) . . ? C7 N1 C1 116.9(5) . . ? C15 N1 C1 116.3(5) . . ? C30 N2 C25 124.0(5) . . ? C30 N2 C4 119.1(5) . . ? C25 N2 C4 116.9(5) . . ? C7 N3 C11 118.2(6) . . ? C14 N4 N5 111.8(7) . . ? C14 N4 C11 127.4(6) . . ? N5 N4 C11 120.7(7) . . ? C12 N5 N4 101.9(8) . . ? C15 N6 C19 117.1(6) . . ? C22 N7 N8 111.8(7) . . ? C22 N7 C19 127.7(8) . . ? N8 N7 C19 120.5(7) . . ? C20 N8 N7 103.3(10) . . ? C23 N9 C27 116.8(6) . . ? C23 N9 Cd1 121.0(4) . . ? C27 N9 Cd1 121.7(4) . . ? C28 N10 C32 116.7(6) . . ? C28 N10 Cd1 120.6(4) . 2_656 ? C32 N10 Cd1 122.0(4) . 2_656 ? C6 C1 C2 118.9(6) . . ? C6 C1 N1 120.9(6) . . ? C2 C1 N1 120.2(6) . . ? C3 C2 C1 120.3(6) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C4 C3 C2 119.3(6) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 121.2(6) . . ? C5 C4 N2 120.3(5) . . ? C3 C4 N2 118.5(5) . . ? C4 C5 C6 119.1(6) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C1 C6 C5 121.1(6) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? N3 C7 C8 122.1(7) . . ? N3 C7 N1 115.9(6) . . ? C8 C7 N1 122.0(7) . . ? C9 C8 C7 117.6(8) . . ? C9 C8 H8 121.2 . . ? C7 C8 H8 121.2 . . ? C8 C9 C10 121.6(8) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C11 C10 C9 116.1(8) . . ? C11 C10 H10 122.0 . . ? C9 C10 H10 122.0 . . ? N3 C11 C10 124.4(8) . . ? N3 C11 N4 114.2(6) . . ? C10 C11 N4 121.4(7) . . ? N5 C12 C13 114.8(9) . . ? N5 C12 H12 122.6 . . ? C13 C12 H12 122.6 . . ? C14 C13 C12 104.1(9) . . ? C14 C13 H13 128.0 . . ? C12 C13 H13 128.0 . . ? C13 C14 N4 107.5(8) . . ? C13 C14 H14 126.3 . . ? N4 C14 H14 126.3 . . ? N6 C15 C16 122.8(7) . . ? N6 C15 N1 114.1(6) . . ? C16 C15 N1 123.0(6) . . ? C17 C16 C15 118.2(7) . . ? C17 C16 H16 120.9 . . ? C15 C16 H16 120.9 . . ? C18 C17 C16 120.1(7) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 116.9(7) . . ? C17 C18 H18 121.5 . . ? C19 C18 H18 121.5 . . ? N6 C19 C18 124.9(7) . . ? N6 C19 N7 115.0(7) . . ? C18 C19 N7 120.0(7) . . ? N8 C20 C21 113.9(11) . . ? N8 C20 H20 123.0 . . ? C21 C20 H20 123.0 . . ? C20 C21 C22 103.7(10) . . ? C20 C21 H21 128.2 . . ? C22 C21 H21 128.2 . . ? N7 C22 C21 107.3(11) . . ? N7 C22 H22 126.3 . . ? C21 C22 H22 126.3 . . ? N9 C23 C24 124.3(6) . . ? N9 C23 H23 117.9 . . ? C24 C23 H23 117.9 . . ? C23 C24 C25 118.9(6) . . ? C23 C24 H24 120.5 . . ? C25 C24 H24 120.5 . . ? N2 C25 C24 120.0(5) . . ? N2 C25 C26 123.6(5) . . ? C24 C25 C26 116.3(6) . . ? C27 C26 C25 119.9(6) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? N9 C27 C26 123.8(6) . . ? N9 C27 H27 118.1 . . ? C26 C27 H27 118.1 . . ? N10 C28 C29 124.3(6) . . ? N10 C28 H28 117.9 . . ? C29 C28 H28 117.9 . . ? C28 C29 C30 119.2(6) . . ? C28 C29 H29 120.4 . . ? C30 C29 H29 120.4 . . ? C29 C30 C31 117.4(6) . . ? C29 C30 N2 120.0(5) . . ? C31 C30 N2 122.6(6) . . ? C32 C31 C30 118.7(6) . . ? C32 C31 H31 120.6 . . ? C30 C31 H31 120.6 . . ? N10 C32 C31 123.5(6) . . ? N10 C32 H32 118.3 . . ? C31 C32 H32 118.3 . . ? 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 C14 N4 N5 C12 0.2(8) . . . . ? C11 N4 N5 C12 -176.9(7) . . . . ? C22 N7 N8 C20 0.2(11) . . . . ? C19 N7 N8 C20 178.3(8) . . . . ? N10 Cd1 N9 C23 171.1(6) 2_646 . . . ? I2 Cd1 N9 C23 56.7(6) . . . . ? I1 Cd1 N9 C23 -81.3(6) . . . . ? N10 Cd1 N9 C27 -18.1(5) 2_646 . . . ? I2 Cd1 N9 C27 -132.4(5) . . . . ? I1 Cd1 N9 C27 89.5(5) . . . . ? C7 N1 C1 C6 -117.4(7) . . . . ? C15 N1 C1 C6 39.7(9) . . . . ? C7 N1 C1 C2 62.0(8) . . . . ? C15 N1 C1 C2 -140.8(6) . . . . ? C6 C1 C2 C3 2.5(10) . . . . ? N1 C1 C2 C3 -177.0(6) . . . . ? C1 C2 C3 C4 -0.5(10) . . . . ? C2 C3 C4 C5 -1.7(10) . . . . ? C2 C3 C4 N2 177.0(6) . . . . ? C30 N2 C4 C5 -84.4(7) . . . . ? C25 N2 C4 C5 98.0(7) . . . . ? C30 N2 C4 C3 96.8(7) . . . . ? C25 N2 C4 C3 -80.7(7) . . . . ? C3 C4 C5 C6 1.8(10) . . . . ? N2 C4 C5 C6 -176.9(6) . . . . ? C2 C1 C6 C5 -2.4(10) . . . . ? N1 C1 C6 C5 177.1(6) . . . . ? C4 C5 C6 C1 0.3(10) . . . . ? C11 N3 C7 C8 -2.3(10) . . . . ? C11 N3 C7 N1 179.3(6) . . . . ? C15 N1 C7 N3 -139.9(6) . . . . ? C1 N1 C7 N3 15.7(9) . . . . ? C15 N1 C7 C8 41.7(10) . . . . ? C1 N1 C7 C8 -162.7(6) . . . . ? N3 C7 C8 C9 1.3(11) . . . . ? N1 C7 C8 C9 179.6(7) . . . . ? C7 C8 C9 C10 -0.4(12) . . . . ? C8 C9 C10 C11 0.4(12) . . . . ? C7 N3 C11 C10 2.4(10) . . . . ? C7 N3 C11 N4 -179.7(6) . . . . ? C9 C10 C11 N3 -1.4(12) . . . . ? C9 C10 C11 N4 -179.2(7) . . . . ? C14 N4 C11 N3 -0.8(10) . . . . ? N5 N4 C11 N3 175.8(6) . . . . ? C14 N4 C11 C10 177.1(7) . . . . ? N5 N4 C11 C10 -6.3(10) . . . . ? N4 N5 C12 C13 -1.4(10) . . . . ? N5 C12 C13 C14 2.1(11) . . . . ? C12 C13 C14 N4 -1.8(9) . . . . ? N5 N4 C14 C13 1.1(9) . . . . ? C11 N4 C14 C13 177.9(7) . . . . ? C19 N6 C15 C16 2.4(9) . . . . ? C19 N6 C15 N1 -174.1(5) . . . . ? C7 N1 C15 N6 -158.7(6) . . . . ? C1 N1 C15 N6 45.5(8) . . . . ? C7 N1 C15 C16 24.8(10) . . . . ? C1 N1 C15 C16 -130.9(7) . . . . ? N6 C15 C16 C17 -1.5(10) . . . . ? N1 C15 C16 C17 174.6(6) . . . . ? C15 C16 C17 C18 0.1(10) . . . . ? C16 C17 C18 C19 0.4(11) . . . . ? C15 N6 C19 C18 -1.8(10) . . . . ? C15 N6 C19 N7 179.8(6) . . . . ? C17 C18 C19 N6 0.5(11) . . . . ? C17 C18 C19 N7 178.7(6) . . . . ? C22 N7 C19 N6 -4.2(12) . . . . ? N8 N7 C19 N6 178.0(7) . . . . ? C22 N7 C19 C18 177.3(9) . . . . ? N8 N7 C19 C18 -0.4(10) . . . . ? N7 N8 C20 C21 1.0(13) . . . . ? N8 C20 C21 C22 -1.8(15) . . . . ? N8 N7 C22 C21 -1.3(12) . . . . ? C19 N7 C22 C21 -179.2(9) . . . . ? C20 C21 C22 N7 1.8(14) . . . . ? C27 N9 C23 C24 -2.3(12) . . . . ? Cd1 N9 C23 C24 168.9(6) . . . . ? N9 C23 C24 C25 -0.1(13) . . . . ? C30 N2 C25 C24 151.3(6) . . . . ? C4 N2 C25 C24 -31.3(8) . . . . ? C30 N2 C25 C26 -32.5(9) . . . . ? C4 N2 C25 C26 144.9(6) . . . . ? C23 C24 C25 N2 179.1(7) . . . . ? C23 C24 C25 C26 2.7(10) . . . . ? N2 C25 C26 C27 -179.2(6) . . . . ? C24 C25 C26 C27 -2.9(9) . . . . ? C23 N9 C27 C26 2.1(10) . . . . ? Cd1 N9 C27 C26 -169.1(5) . . . . ? C25 C26 C27 N9 0.5(10) . . . . ? C32 N10 C28 C29 -4.4(11) . . . . ? Cd1 N10 C28 C29 165.6(6) 2_656 . . . ? N10 C28 C29 C30 1.7(11) . . . . ? C28 C29 C30 C31 2.4(10) . . . . ? C28 C29 C30 N2 -178.9(6) . . . . ? C25 N2 C30 C29 162.3(6) . . . . ? C4 N2 C30 C29 -15.0(9) . . . . ? C25 N2 C30 C31 -19.0(10) . . . . ? C4 N2 C30 C31 163.7(6) . . . . ? C29 C30 C31 C32 -3.6(10) . . . . ? N2 C30 C31 C32 177.7(6) . . . . ? C28 N10 C32 C31 3.0(10) . . . . ? Cd1 N10 C32 C31 -166.9(5) 2_656 . . . ? C30 C31 C32 N10 1.0(11) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.157 _refine_diff_density_min -1.472 _refine_diff_density_rms 0.112 _database_code_depnum_ccdc_archive 'CCDC 968023' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_120930c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C75 H70 Cl2 Co2 N25 O12 S2' _chemical_formula_weight 1766.44 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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 36.645(3) _cell_length_b 8.7390(6) _cell_length_c 25.427(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.3040(10) _cell_angle_gamma 90.00 _cell_volume 7890.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3016 _cell_measurement_theta_min 2.294 _cell_measurement_theta_max 20.647 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3644 _exptl_absorpt_coefficient_mu 0.620 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8359 _exptl_absorpt_correction_T_max 0.9128 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19342 _diffrn_reflns_av_R_equivalents 0.0719 _diffrn_reflns_av_sigmaI/netI 0.0874 _diffrn_reflns_limit_h_min -43 _diffrn_reflns_limit_h_max 43 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.02 _reflns_number_total 6953 _reflns_number_gt 4064 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material '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^ > 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_number_reflns 6953 _refine_ls_number_parameters 582 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1042 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.1753 _refine_ls_wR_factor_gt 0.1585 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 Co1 Co 0.580249(17) 0.77737(7) 0.56761(2) 0.0368(2) Uani 1 1 d . . . Cl1 Cl 0.73696(4) 0.44024(17) 0.59337(6) 0.0604(4) Uani 1 1 d . . . N1 N 0.63078(10) 0.6274(4) 0.48534(14) 0.0408(10) Uani 1 1 d . . . N2 N 0.68033(10) 0.4915(5) 0.29558(14) 0.0442(10) Uani 1 1 d . . . N3 N 0.62933(10) 0.8415(4) 0.54426(14) 0.0359(9) Uani 1 1 d . . . N4 N 0.62324(10) 1.0548(4) 0.59734(15) 0.0388(9) Uani 1 1 d . . . N5 N 0.59100(10) 0.9897(4) 0.60570(15) 0.0418(10) Uani 1 1 d . . . N6 N 0.58226(10) 0.5641(4) 0.53044(14) 0.0386(9) Uani 1 1 d . . . N7 N 0.53281(11) 0.5178(5) 0.57105(16) 0.0456(10) Uani 1 1 d . . . N8 N 0.53366(11) 0.6690(5) 0.58513(16) 0.0443(10) Uani 1 1 d . . . N9 N 0.61284(10) 0.6731(4) 0.64582(14) 0.0362(9) Uani 1 1 d . . . N10 N 0.79785(13) 0.5483(7) 0.3163(2) 0.0766(16) Uani 1 1 d . . . N11 N 0.54772(12) 0.8732(5) 0.49527(18) 0.0537(11) Uani 1 1 d . . . N12 N 0.6274(3) 0.9656(9) 0.8205(3) 0.120(2) Uani 1 1 d . . . N13 N 0.5000 0.578(14) 0.7500 0.15(3) Uani 0.32(3) 2 d SP . 1 N13' N 0.5000 0.38(7) 0.7500 0.16(9) Uani 0.68(3) 2 d SP . 2 O1 O 0.69679(12) 0.4345(6) 0.5814(2) 0.1007(16) Uani 1 1 d . . . O2 O 0.74943(15) 0.3140(7) 0.5676(3) 0.131(2) Uani 1 1 d . . . O3 O 0.74764(15) 0.5748(6) 0.5699(2) 0.1155(18) Uani 1 1 d . . . O4 O 0.75127(19) 0.4482(8) 0.6502(2) 0.160(3) Uani 1 1 d . . . O5 O 0.5714(3) 0.9811(13) 0.7589(4) 0.214(4) Uani 1 1 d . . . O6 O 0.533(6) 0.37(3) 0.765(6) 0.15(5) Uani 0.159(17) 1 d P . 1 O6' O 0.5501(13) 0.290(6) 0.7410(15) 0.163(13) Uani 0.341(17) 1 d P . 2 O7 O 0.5000 0.8313(17) 0.7500 0.219(5) Uani 1 2 d S A 2 H7C H 0.5192 0.8880 0.7524 0.263 Uiso 0.50 1 d PR A 2 S1 S 0.53239(5) 0.92293(19) 0.38329(6) 0.0708(5) Uani 1 1 d . . . C1 C 0.64322(13) 0.5855(5) 0.43618(18) 0.0389(11) Uani 1 1 d . . . C2 C 0.67536(13) 0.4987(6) 0.43919(19) 0.0452(12) Uani 1 1 d . . . H2 H 0.6892 0.4628 0.4726 0.054 Uiso 1 1 calc R . . C3 C 0.68678(13) 0.4657(6) 0.39280(19) 0.0461(13) Uani 1 1 d . . . H3 H 0.7083 0.4069 0.3950 0.055 Uiso 1 1 calc R . . C4 C 0.66646(13) 0.5195(5) 0.34269(18) 0.0393(11) Uani 1 1 d . . . C5 C 0.63380(13) 0.6047(6) 0.33930(19) 0.0436(12) Uani 1 1 d . . . H5 H 0.6199 0.6400 0.3059 0.052 Uiso 1 1 calc R . . C6 C 0.62209(13) 0.6366(6) 0.38657(18) 0.0440(12) Uani 1 1 d . . . H6 H 0.6001 0.6921 0.3846 0.053 Uiso 1 1 calc R . . C7 C 0.64628(13) 0.7670(5) 0.50983(17) 0.0376(11) Uani 1 1 d . . . C8 C 0.67761(14) 0.8291(6) 0.4960(2) 0.0509(14) Uani 1 1 d . . . H8 H 0.6895 0.7761 0.4732 0.061 Uiso 1 1 calc R . . C9 C 0.69101(15) 0.9711(6) 0.5167(2) 0.0574(15) Uani 1 1 d . . . H9 H 0.7119 1.0134 0.5074 0.069 Uiso 1 1 calc R . . C10 C 0.67376(14) 1.0504(6) 0.5510(2) 0.0505(13) Uani 1 1 d . . . H10 H 0.6822 1.1459 0.5650 0.061 Uiso 1 1 calc R . . C11 C 0.64335(13) 0.9800(5) 0.56324(18) 0.0390(11) Uani 1 1 d . . . C12 C 0.57934(14) 1.0869(6) 0.63829(19) 0.0478(13) Uani 1 1 d . . . H12 H 0.5580 1.0720 0.6512 0.057 Uiso 1 1 calc R . . C13 C 0.60289(15) 1.2137(6) 0.6508(2) 0.0549(14) Uani 1 1 d . . . H13 H 0.6004 1.2967 0.6725 0.066 Uiso 1 1 calc R . . C14 C 0.63078(14) 1.1891(6) 0.6239(2) 0.0509(14) Uani 1 1 d . . . H14 H 0.6510 1.2534 0.6241 0.061 Uiso 1 1 calc R . . C15 C 0.60522(13) 0.5228(6) 0.49931(18) 0.0420(12) Uani 1 1 d . . . C16 C 0.60410(15) 0.3703(6) 0.4788(2) 0.0559(14) Uani 1 1 d . . . H16 H 0.6208 0.3389 0.4587 0.067 Uiso 1 1 calc R . . C17 C 0.57765(16) 0.2704(6) 0.4897(2) 0.0582(15) Uani 1 1 d . . . H17 H 0.5767 0.1706 0.4766 0.070 Uiso 1 1 calc R . . C18 C 0.55277(15) 0.3148(6) 0.5193(2) 0.0526(14) Uani 1 1 d . . . H18 H 0.5341 0.2496 0.5252 0.063 Uiso 1 1 calc R . . C19 C 0.55706(14) 0.4619(6) 0.53968(18) 0.0435(12) Uani 1 1 d . . . C20 C 0.50802(15) 0.6835(7) 0.6136(2) 0.0611(16) Uani 1 1 d . . . H20 H 0.5027 0.7747 0.6291 0.073 Uiso 1 1 calc R . . C21 C 0.49013(17) 0.5456(8) 0.6174(3) 0.0762(19) Uani 1 1 d . . . H21 H 0.4710 0.5274 0.6347 0.091 Uiso 1 1 calc R . . C22 C 0.50662(16) 0.4425(7) 0.5905(2) 0.0640(16) Uani 1 1 d . . . H22 H 0.5009 0.3388 0.5861 0.077 Uiso 1 1 calc R . . C23 C 0.64518(12) 0.5956(5) 0.64930(17) 0.0362(11) Uani 1 1 d . . . H23 H 0.6529 0.5799 0.6175 0.043 Uiso 1 1 calc R . . C24 C 0.66737(12) 0.5385(5) 0.69681(17) 0.0366(11) Uani 1 1 d . . . H24 H 0.6893 0.4859 0.6963 0.044 Uiso 1 1 calc R . . C25 C 0.65736(13) 0.5585(5) 0.74606(17) 0.0381(11) Uani 1 1 d . . . C26 C 0.62295(14) 0.6335(6) 0.74221(19) 0.0497(13) Uani 1 1 d . . . H26 H 0.6139 0.6461 0.7730 0.060 Uiso 1 1 calc R . . C27 C 0.60259(14) 0.6884(6) 0.69312(19) 0.0470(13) Uani 1 1 d . . . H27 H 0.5802 0.7396 0.6923 0.056 Uiso 1 1 calc R . . C28 C 0.77956(17) 0.4265(8) 0.2904(2) 0.0732(18) Uani 1 1 d . . . H28 H 0.7934 0.3538 0.2769 0.088 Uiso 1 1 calc R . . C29 C 0.74060(14) 0.4022(7) 0.2824(2) 0.0570(15) Uani 1 1 d . . . H29 H 0.7291 0.3157 0.2643 0.068 Uiso 1 1 calc R . . C30 C 0.72021(13) 0.5094(6) 0.30187(18) 0.0442(12) Uani 1 1 d . . . C31 C 0.73851(14) 0.6362(6) 0.32872(19) 0.0503(13) Uani 1 1 d . . . H31 H 0.7253 0.7115 0.3421 0.060 Uiso 1 1 calc R . . C32 C 0.77712(16) 0.6478(8) 0.3352(2) 0.0633(16) Uani 1 1 d . . . H32 H 0.7893 0.7318 0.3542 0.076 Uiso 1 1 calc R . . C33 C 0.54156(13) 0.8947(6) 0.4486(2) 0.0479(13) Uani 1 1 d . . . C34 C 0.5903(5) 0.9527(16) 0.8047(6) 0.172(5) Uani 1 1 d . . . H34 H 0.5777 0.9198 0.8302 0.207 Uiso 1 1 calc R . . C35 C 0.6446(4) 0.9270(14) 0.8767(5) 0.225(7) Uani 1 1 d . . . H35A H 0.6291 0.8545 0.8894 0.337 Uiso 1 1 calc R . . H35B H 0.6472 1.0178 0.8985 0.337 Uiso 1 1 calc R . . H35C H 0.6690 0.8831 0.8794 0.337 Uiso 1 1 calc R . . C36 C 0.6503(3) 1.0142(13) 0.7840(5) 0.176(5) Uani 1 1 d . . . H36A H 0.6631 0.9271 0.7739 0.264 Uiso 1 1 calc R . . H36B H 0.6685 1.0881 0.8020 0.264 Uiso 1 1 calc R . . H36C H 0.6344 1.0591 0.7520 0.264 Uiso 1 1 calc R . . C37 C 0.5000 0.42(16) 0.7500 0.2(2) Uani 0.32(3) 2 d SP . 1 H37 H 0.4782 0.3648 0.7398 0.187 Uiso 0.159(17) 1 d PR . 1 C38 C 0.4645(11) 0.663(8) 0.7334(14) 0.142(19) Uani 0.32(3) 1 d P . 1 H39A H 0.4682 0.7650 0.7477 0.213 Uiso 0.32(3) 1 d PR . 1 H39B H 0.4453 0.6130 0.7469 0.213 Uiso 0.32(3) 1 d PR . 1 H39C H 0.4568 0.6674 0.6944 0.213 Uiso 0.32(3) 1 d PR . 1 C37' C 0.517(2) 0.249(7) 0.742(2) 0.153(18) Uani 0.341(17) 1 d P . 2 H37' H 0.5069 0.1517 0.7372 0.183 Uiso 0.341(17) 1 d PR . 2 C38' C 0.526(3) 0.518(12) 0.756(2) 0.147(19) Uani 0.341(17) 1 d P . 2 H38A H 0.5512 0.4864 0.7700 0.220 Uiso 0.341(17) 1 d PR . 2 H38B H 0.5188 0.5914 0.7798 0.220 Uiso 0.341(17) 1 d PR . 2 H38C H 0.5232 0.5647 0.7207 0.220 Uiso 0.341(17) 1 d PR . 2 C39' C 0.461(4) 0.40(2) 0.754(5) 0.15(4) Uani 0.341(17) 1 d P . 2 H39D H 0.4459 0.3238 0.7334 0.221 Uiso 0.341(17) 1 d PR . 2 H39E H 0.4521 0.5007 0.7412 0.221 Uiso 0.341(17) 1 d PR . 2 H39F H 0.4607 0.3922 0.7918 0.221 Uiso 0.341(17) 1 d PR . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0386(4) 0.0346(4) 0.0356(4) -0.0010(3) 0.0063(3) -0.0061(3) Cl1 0.0643(10) 0.0605(10) 0.0554(9) -0.0003(7) 0.0128(7) -0.0008(7) N1 0.050(2) 0.040(2) 0.034(2) -0.0062(18) 0.0133(18) -0.007(2) N2 0.041(2) 0.061(3) 0.029(2) -0.0091(19) 0.0069(18) -0.006(2) N3 0.041(2) 0.032(2) 0.033(2) -0.0029(17) 0.0061(17) -0.0055(18) N4 0.044(2) 0.032(2) 0.040(2) -0.0064(18) 0.0092(19) -0.0066(18) N5 0.043(2) 0.041(2) 0.043(2) -0.0033(19) 0.0134(19) -0.005(2) N6 0.045(2) 0.038(2) 0.031(2) 0.0019(17) 0.0050(18) -0.0091(19) N7 0.047(3) 0.041(3) 0.047(2) 0.006(2) 0.009(2) -0.015(2) N8 0.042(2) 0.045(3) 0.045(2) 0.002(2) 0.009(2) -0.0057(19) N9 0.036(2) 0.040(2) 0.031(2) -0.0013(17) 0.0046(17) -0.0027(18) N10 0.047(3) 0.113(5) 0.064(3) 0.007(3) 0.002(3) -0.003(3) N11 0.055(3) 0.049(3) 0.052(3) 0.006(2) 0.002(2) -0.012(2) N12 0.138(7) 0.118(6) 0.102(6) -0.036(5) 0.027(6) 0.023(5) N13 0.13(7) 0.16(9) 0.14(4) 0.000 0.01(5) 0.000 N13' 0.15(14) 0.2(3) 0.14(4) 0.000 0.01(6) 0.000 O1 0.067(3) 0.124(4) 0.118(4) -0.029(3) 0.037(3) -0.001(3) O2 0.104(4) 0.109(4) 0.190(6) -0.040(4) 0.055(4) 0.031(3) O3 0.144(5) 0.088(4) 0.124(4) 0.017(3) 0.052(4) -0.030(3) O4 0.183(6) 0.207(7) 0.069(4) 0.015(4) -0.005(4) -0.036(5) O5 0.223(10) 0.284(12) 0.132(7) -0.011(7) 0.035(7) 0.096(8) O6 0.09(8) 0.19(15) 0.15(9) 0.00(8) 0.02(6) 0.04(7) O6' 0.15(3) 0.18(4) 0.14(2) -0.01(2) 0.01(2) 0.01(3) O7 0.205(13) 0.234(15) 0.191(11) 0.000 -0.003(9) 0.000 S1 0.0881(12) 0.0696(11) 0.0536(9) 0.0134(8) 0.0156(8) -0.0053(9) C1 0.044(3) 0.040(3) 0.032(3) -0.007(2) 0.009(2) -0.006(2) C2 0.050(3) 0.046(3) 0.036(3) -0.001(2) 0.004(2) 0.004(3) C3 0.047(3) 0.048(3) 0.041(3) -0.008(2) 0.006(2) 0.005(2) C4 0.043(3) 0.041(3) 0.032(3) -0.005(2) 0.004(2) -0.004(2) C5 0.044(3) 0.048(3) 0.036(3) -0.001(2) 0.005(2) 0.001(2) C6 0.045(3) 0.045(3) 0.040(3) -0.004(2) 0.007(2) 0.003(2) C7 0.042(3) 0.038(3) 0.032(2) -0.006(2) 0.007(2) -0.010(2) C8 0.053(3) 0.057(4) 0.048(3) -0.013(3) 0.021(3) -0.012(3) C9 0.056(3) 0.063(4) 0.058(3) -0.008(3) 0.023(3) -0.023(3) C10 0.055(3) 0.047(3) 0.052(3) -0.011(3) 0.017(3) -0.015(3) C11 0.041(3) 0.038(3) 0.036(3) -0.003(2) 0.006(2) -0.007(2) C12 0.050(3) 0.050(3) 0.045(3) -0.005(3) 0.015(2) 0.002(3) C13 0.064(4) 0.049(3) 0.051(3) -0.015(3) 0.013(3) -0.001(3) C14 0.055(3) 0.043(3) 0.053(3) -0.013(3) 0.010(3) -0.011(3) C15 0.051(3) 0.036(3) 0.032(3) -0.002(2) -0.001(2) -0.006(2) C16 0.067(4) 0.045(3) 0.055(3) -0.007(3) 0.013(3) -0.005(3) C17 0.079(4) 0.038(3) 0.053(3) -0.011(3) 0.009(3) -0.021(3) C18 0.061(3) 0.038(3) 0.054(3) 0.004(3) 0.007(3) -0.019(3) C19 0.052(3) 0.039(3) 0.034(3) 0.004(2) -0.001(2) -0.007(2) C20 0.052(3) 0.069(4) 0.064(4) 0.006(3) 0.020(3) -0.004(3) C21 0.065(4) 0.092(5) 0.079(5) 0.011(4) 0.032(4) -0.013(4) C22 0.063(4) 0.062(4) 0.067(4) 0.007(3) 0.016(3) -0.025(3) C23 0.041(3) 0.041(3) 0.028(3) -0.002(2) 0.011(2) -0.006(2) C24 0.035(3) 0.039(3) 0.035(3) -0.001(2) 0.006(2) 0.000(2) C25 0.041(3) 0.042(3) 0.030(3) 0.003(2) 0.006(2) 0.002(2) C26 0.054(3) 0.066(4) 0.033(3) 0.002(3) 0.017(2) 0.009(3) C27 0.046(3) 0.057(4) 0.038(3) 0.003(2) 0.010(2) 0.012(2) C28 0.056(4) 0.099(6) 0.061(4) -0.006(4) 0.009(3) 0.022(4) C29 0.047(3) 0.072(4) 0.048(3) -0.012(3) 0.002(3) 0.005(3) C30 0.040(3) 0.058(3) 0.032(3) 0.002(2) 0.004(2) 0.001(3) C31 0.047(3) 0.053(4) 0.047(3) 0.001(3) 0.004(2) -0.004(3) C32 0.056(4) 0.073(4) 0.055(4) 0.005(3) 0.002(3) -0.018(3) C33 0.040(3) 0.040(3) 0.061(4) 0.003(3) 0.009(3) -0.004(2) C34 0.161(13) 0.196(13) 0.151(12) -0.043(10) 0.022(10) 0.052(10) C35 0.329(18) 0.166(12) 0.140(11) 0.008(9) -0.014(11) 0.099(12) C36 0.219(13) 0.148(10) 0.175(11) -0.033(8) 0.075(10) -0.026(9) C37 0.1(3) 0.2(7) 0.14(11) 0.000 0.01(14) 0.000 C38 0.13(3) 0.16(5) 0.13(3) 0.00(3) 0.02(2) 0.00(3) C37' 0.13(5) 0.17(6) 0.14(4) -0.01(3) 0.02(3) 0.02(5) C38' 0.13(6) 0.16(7) 0.14(4) 0.00(5) 0.02(4) 0.00(8) C39' 0.13(7) 0.17(10) 0.14(6) 0.00(7) 0.02(4) 0.00(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 Co1 N5 2.085(4) . ? Co1 N8 2.094(4) . ? Co1 N6 2.100(4) . ? Co1 N11 2.103(5) . ? Co1 N3 2.105(3) . ? Co1 N9 2.244(4) . ? Cl1 O4 1.413(5) . ? Cl1 O2 1.415(5) . ? Cl1 O3 1.417(5) . ? Cl1 O1 1.428(4) . ? N1 C15 1.416(6) . ? N1 C7 1.422(6) . ? N1 C1 1.478(5) . ? N2 C25 1.400(5) 6_565 ? N2 C4 1.433(5) . ? N2 C30 1.439(5) . ? N3 C11 1.356(6) . ? N3 C7 1.358(5) . ? N4 C14 1.349(6) . ? N4 N5 1.374(5) . ? N4 C11 1.427(5) . ? N5 C12 1.329(6) . ? N6 C15 1.339(6) . ? N6 C19 1.346(6) . ? N7 C22 1.353(6) . ? N7 N8 1.368(5) . ? N7 C19 1.419(6) . ? N8 C20 1.327(6) . ? N9 C23 1.349(5) . ? N9 C27 1.352(5) . ? N10 C32 1.320(7) . ? N10 C28 1.341(8) . ? N11 C33 1.166(6) . ? N12 C34 1.322(13) . ? N12 C35 1.452(12) . ? N12 C36 1.463(11) . ? N13 C37 1.3(15) . ? N13 C38 1.47(6) . ? N13 C38 1.47(6) 2_656 ? N13 H38B 0.8975 . ? N13 H38C 1.2662 . ? N13' C37' 1.4(5) 2_656 ? N13' C37' 1.4(5) . ? N13' C39' 1.46(15) 2_656 ? N13' C39' 1.46(15) . ? N13' C38' 1.5(5) 2_656 ? N13' C38' 1.5(5) . ? N13' H37 0.7901 . ? O5 C34 1.225(13) . ? O6 C37 1.3(6) . ? O6 H38A 1.1989 . ? O6' C39' 1.08(19) 2_656 ? O6' C37' 1.26(7) . ? O7 H7C 0.8501 . ? O7 H39A 1.2907 . ? S1 C33 1.631(6) . ? C1 C6 1.381(6) . ? C1 C2 1.387(6) . ? C2 C3 1.376(6) . ? C2 H2 0.9300 . ? C3 C4 1.389(6) . ? C3 H3 0.9300 . ? C4 C5 1.394(6) . ? C5 C6 1.401(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.391(6) . ? C8 C9 1.390(7) . ? C8 H8 0.9300 . ? C9 C10 1.382(7) . ? C9 H9 0.9300 . ? C10 C11 1.374(6) . ? C10 H10 0.9300 . ? C12 C13 1.392(7) . ? C12 H12 0.9300 . ? C13 C14 1.379(7) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.428(7) . ? C16 C17 1.382(7) . ? C16 H16 0.9300 . ? C17 C18 1.374(7) . ? C17 H17 0.9300 . ? C18 C19 1.381(7) . ? C18 H18 0.9300 . ? C20 C21 1.387(8) . ? C20 H20 0.9300 . ? C21 C22 1.361(8) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.373(6) . ? C23 H23 0.9300 . ? C24 C25 1.400(6) . ? C24 H24 0.9300 . ? C25 N2 1.400(5) 6_566 ? C25 C26 1.403(6) . ? C26 C27 1.373(6) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 C29 1.407(7) . ? C28 H28 0.9300 . ? C29 C30 1.366(7) . ? C29 H29 0.9300 . ? C30 C31 1.384(7) . ? C31 C32 1.387(7) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? C34 H34 0.9300 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 O6 1.3(6) 2_656 ? C37 H37 0.9300 . ? C38 H39A 0.9600 . ? C38 H39B 0.9600 . ? C38 H39C 0.9600 . ? C37' C37' 1.43(17) 2_656 ? C37' C39' 1.53(19) 2_656 ? C37' H37' 0.9300 . ? C38' C39' 1.18(18) 2_656 ? C38' C38' 1.8(2) 2_656 ? C38' H38A 0.9600 . ? C38' H38B 0.9600 . ? C38' H38C 0.9600 . ? C39' O6' 1.08(19) 2_656 ? C39' C38' 1.18(18) 2_656 ? C39' C37' 1.53(19) 2_656 ? C39' H37 0.8599 . ? C39' H39D 0.9600 . ? C39' H39E 0.9600 . ? C39' H39F 0.9600 . ? 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 N5 Co1 N8 111.96(15) . . ? N5 Co1 N6 167.32(14) . . ? N8 Co1 N6 79.37(15) . . ? N5 Co1 N11 93.04(16) . . ? N8 Co1 N11 92.89(16) . . ? N6 Co1 N11 92.01(16) . . ? N5 Co1 N3 79.49(14) . . ? N8 Co1 N3 168.21(15) . . ? N6 Co1 N3 88.97(14) . . ? N11 Co1 N3 89.22(15) . . ? N5 Co1 N9 87.23(14) . . ? N8 Co1 N9 84.92(14) . . ? N6 Co1 N9 88.18(14) . . ? N11 Co1 N9 177.72(15) . . ? N3 Co1 N9 93.06(13) . . ? O4 Cl1 O2 115.5(4) . . ? O4 Cl1 O3 108.6(4) . . ? O2 Cl1 O3 107.3(3) . . ? O4 Cl1 O1 108.8(3) . . ? O2 Cl1 O1 107.9(3) . . ? O3 Cl1 O1 108.5(3) . . ? C15 N1 C7 131.4(4) . . ? C15 N1 C1 114.4(4) . . ? C7 N1 C1 114.2(3) . . ? C25 N2 C4 123.1(4) 6_565 . ? C25 N2 C30 120.2(4) 6_565 . ? C4 N2 C30 116.6(4) . . ? C11 N3 C7 117.6(4) . . ? C11 N3 Co1 114.3(3) . . ? C7 N3 Co1 127.8(3) . . ? C14 N4 N5 111.1(4) . . ? C14 N4 C11 129.1(4) . . ? N5 N4 C11 119.8(4) . . ? C12 N5 N4 104.7(4) . . ? C12 N5 Co1 143.7(3) . . ? N4 N5 Co1 111.5(3) . . ? C15 N6 C19 118.9(4) . . ? C15 N6 Co1 127.0(3) . . ? C19 N6 Co1 114.1(3) . . ? C22 N7 N8 110.3(4) . . ? C22 N7 C19 129.5(5) . . ? N8 N7 C19 120.2(4) . . ? C20 N8 N7 105.2(4) . . ? C20 N8 Co1 142.9(4) . . ? N7 N8 Co1 110.4(3) . . ? C23 N9 C27 115.1(4) . . ? C23 N9 Co1 121.9(3) . . ? C27 N9 Co1 123.0(3) . . ? C32 N10 C28 116.1(5) . . ? C33 N11 Co1 151.5(4) . . ? C34 N12 C35 116.3(12) . . ? C34 N12 C36 122.7(10) . . ? C35 N12 C36 120.9(11) . . ? C37 N13 C38 120(4) . . ? C37 N13 C38 120(4) . 2_656 ? C38 N13 C38 119(8) . 2_656 ? C37 N13 H38B 97.4 . . ? C38 N13 H38B 128.3 . . ? C38 N13 H38B 41.3 2_656 . ? C37 N13 H38C 84.7 . . ? C38 N13 H38C 123.6 . . ? C38 N13 H38C 62.6 2_656 . ? H38B N13 H38C 91.2 . . ? C37' N13' C37' 63(10) 2_656 . ? C37' N13' C39' 127(10) 2_656 2_656 ? C37' N13' C39' 66(10) . 2_656 ? C37' N13' C39' 66(10) 2_656 . ? C37' N13' C39' 127(10) . . ? C39' N13' C39' 167(10) 2_656 . ? C37' N13' C38' 113(6) 2_656 2_656 ? C37' N13' C38' 164(10) . 2_656 ? C39' N13' C38' 120(10) 2_656 2_656 ? C39' N13' C38' 47(10) . 2_656 ? C37' N13' C38' 164(10) 2_656 . ? C37' N13' C38' 113(6) . . ? C39' N13' C38' 47(10) 2_656 . ? C39' N13' C38' 120(10) . . ? C38' N13' C38' 75(10) 2_656 . ? C37' N13' H37 54.4 2_656 . ? C37' N13' H37 104.6 . . ? C39' N13' H37 156.6 2_656 . ? C39' N13' H37 29.2 . . ? C38' N13' H37 64.3 2_656 . ? C38' N13' H37 137.9 . . ? C37 O6 H38A 101.4 . . ? C39' O6' C37' 82(8) 2_656 . ? H7C O7 H39A 170.8 . . ? C6 C1 C2 120.3(4) . . ? C6 C1 N1 118.2(4) . . ? C2 C1 N1 121.6(4) . . ? C3 C2 C1 120.1(4) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 120.5(5) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C3 C4 C5 119.7(4) . . ? C3 C4 N2 119.2(4) . . ? C5 C4 N2 121.1(4) . . ? C4 C5 C6 119.6(4) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C1 C6 C5 119.9(4) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? N3 C7 C8 120.9(4) . . ? N3 C7 N1 119.8(4) . . ? C8 C7 N1 119.3(4) . . ? C9 C8 C7 119.3(5) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C10 C9 C8 120.8(5) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C11 C10 C9 116.2(5) . . ? C11 C10 H10 121.9 . . ? C9 C10 H10 121.9 . . ? N3 C11 C10 125.2(4) . . ? N3 C11 N4 114.7(4) . . ? C10 C11 N4 120.1(4) . . ? N5 C12 C13 112.0(4) . . ? N5 C12 H12 124.0 . . ? C13 C12 H12 124.0 . . ? C14 C13 C12 104.9(5) . . ? C14 C13 H13 127.6 . . ? C12 C13 H13 127.6 . . ? N4 C14 C13 107.3(5) . . ? N4 C14 H14 126.3 . . ? C13 C14 H14 126.3 . . ? N6 C15 N1 121.7(4) . . ? N6 C15 C16 120.1(4) . . ? N1 C15 C16 118.2(4) . . ? C17 C16 C15 118.4(5) . . ? C17 C16 H16 120.8 . . ? C15 C16 H16 120.8 . . ? C18 C17 C16 121.6(5) . . ? C18 C17 H17 119.2 . . ? C16 C17 H17 119.2 . . ? C17 C18 C19 116.1(5) . . ? C17 C18 H18 121.9 . . ? C19 C18 H18 121.9 . . ? N6 C19 C18 124.8(5) . . ? N6 C19 N7 115.0(4) . . ? C18 C19 N7 120.2(4) . . ? N8 C20 C21 111.5(6) . . ? N8 C20 H20 124.3 . . ? C21 C20 H20 124.3 . . ? C22 C21 C20 105.3(5) . . ? C22 C21 H21 127.4 . . ? C20 C21 H21 127.4 . . ? N7 C22 C21 107.8(5) . . ? N7 C22 H22 126.1 . . ? C21 C22 H22 126.1 . . ? N9 C23 C24 124.1(4) . . ? N9 C23 H23 118.0 . . ? C24 C23 H23 118.0 . . ? C23 C24 C25 120.8(4) . . ? C23 C24 H24 119.6 . . ? C25 C24 H24 119.6 . . ? C24 C25 N2 122.2(4) . 6_566 ? C24 C25 C26 115.2(4) . . ? N2 C25 C26 122.6(4) 6_566 . ? C27 C26 C25 120.3(4) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? N9 C27 C26 124.5(4) . . ? N9 C27 H27 117.8 . . ? C26 C27 H27 117.8 . . ? N10 C28 C29 123.8(6) . . ? N10 C28 H28 118.1 . . ? C29 C28 H28 118.1 . . ? C30 C29 C28 118.1(5) . . ? C30 C29 H29 121.0 . . ? C28 C29 H29 121.0 . . ? C29 C30 C31 119.1(5) . . ? C29 C30 N2 121.1(5) . . ? C31 C30 N2 119.8(5) . . ? C30 C31 C32 118.2(5) . . ? C30 C31 H31 120.9 . . ? C32 C31 H31 120.9 . . ? N10 C32 C31 124.8(6) . . ? N10 C32 H32 117.6 . . ? C31 C32 H32 117.6 . . ? N11 C33 S1 179.1(5) . . ? O5 C34 N12 124.7(15) . . ? O5 C34 H34 117.6 . . ? N12 C34 H34 117.6 . . ? N12 C35 H35A 109.5 . . ? N12 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? N12 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? N12 C36 H36A 109.5 . . ? N12 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? N12 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O6 C37 O6 137(10) 2_656 . ? O6 C37 N13 111(10) 2_656 . ? O6 C37 N13 111(10) . . ? O6 C37 H37 12.2 2_656 . ? O6 C37 H37 125.1 . . ? N13 C37 H37 123.6 . . ? N13 C38 H39A 109.2 . . ? N13 C38 H39B 109.9 . . ? H39A C38 H39B 109.5 . . ? N13 C38 H39C 109.3 . . ? H39A C38 H39C 109.5 . . ? H39B C38 H39C 109.5 . . ? N13 C38 H39E 76.2 . . ? H39A C38 H39E 146.8 . . ? H39B C38 H39E 42.1 . . ? H39C C38 H39E 98.7 . . ? O6' C37' N13' 104(10) . . ? O6' C37' C37' 157(6) . 2_656 ? N13' C37' C37' 58(10) . 2_656 ? O6' C37' C39' 44(6) . 2_656 ? N13' C37' C39' 60(10) . 2_656 ? C37' C37' C39' 117(7) 2_656 2_656 ? O6' C37' H37' 128.1 . . ? N13' C37' H37' 127.6 . . ? C37' C37' H37' 70.9 2_656 . ? C39' C37' H37' 172.1 2_656 . ? C39' C38' N13' 65(10) 2_656 . ? C39' C38' C38' 115(10) 2_656 2_656 ? N13' C38' C38' 52(10) . 2_656 ? C39' C38' H38A 54.7 2_656 . ? N13' C38' H38A 109.5 . . ? C38' C38' H38A 158.2 2_656 . ? C39' C38' H38B 153.5 2_656 . ? N13' C38' H38B 109.4 . . ? C38' C38' H38B 71.4 2_656 . ? H38A C38' H38B 109.5 . . ? C39' C38' H38C 96.5 2_656 . ? N13' C38' H38C 109.4 . . ? C38' C38' H38C 89.9 2_656 . ? H38A C38' H38C 109.5 . . ? H38B C38' H38C 109.5 . . ? O6' C39' C38' 173(10) 2_656 2_656 ? O6' C39' N13' 108(10) 2_656 . ? C38' C39' N13' 68(10) 2_656 . ? O6' C39' C37' 54(9) 2_656 2_656 ? C38' C39' C37' 122(10) 2_656 2_656 ? N13' C39' C37' 54(10) . 2_656 ? O6' C39' H37 92.6 2_656 . ? C38' C39' H37 81.8 2_656 . ? N13' C39' H37 26.7 . . ? C37' C39' H37 45.0 2_656 . ? O6' C39' H39D 39.3 2_656 . ? C38' C39' H39D 134.9 2_656 . ? N13' C39' H39D 109.0 . . ? C37' C39' H39D 69.2 2_656 . ? H37 C39' H39D 83.2 . . ? O6' C39' H39E 137.7 2_656 . ? C38' C39' H39E 43.3 2_656 . ? N13' C39' H39E 110.1 . . ? C37' C39' H39E 159.2 2_656 . ? H37 C39' H39E 114.5 . . ? H39D C39' H39E 109.5 . . ? O6' C39' H39F 73.2 2_656 . ? C38' C39' H39F 113.6 2_656 . ? N13' C39' H39F 109.3 . . ? C37' C39' H39F 89.8 2_656 . ? H37 C39' H39F 126.4 . . ? H39D C39' H39F 109.5 . . ? H39E C39' H39F 109.5 . . ? 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 N5 Co1 N3 C11 -0.4(3) . . . . ? N8 Co1 N3 C11 -166.8(6) . . . . ? N6 Co1 N3 C11 -175.2(3) . . . . ? N11 Co1 N3 C11 92.8(3) . . . . ? N9 Co1 N3 C11 -87.0(3) . . . . ? N5 Co1 N3 C7 -175.0(4) . . . . ? N8 Co1 N3 C7 18.7(9) . . . . ? N6 Co1 N3 C7 10.3(4) . . . . ? N11 Co1 N3 C7 -81.7(4) . . . . ? N9 Co1 N3 C7 98.4(4) . . . . ? C14 N4 N5 C12 -0.5(5) . . . . ? C11 N4 N5 C12 -179.5(4) . . . . ? C14 N4 N5 Co1 -177.5(3) . . . . ? C11 N4 N5 Co1 3.5(5) . . . . ? N8 Co1 N5 C12 0.3(6) . . . . ? N6 Co1 N5 C12 -152.0(6) . . . . ? N11 Co1 N5 C12 94.7(6) . . . . ? N3 Co1 N5 C12 -176.7(6) . . . . ? N9 Co1 N5 C12 -83.1(6) . . . . ? N8 Co1 N5 N4 175.4(3) . . . . ? N6 Co1 N5 N4 23.1(8) . . . . ? N11 Co1 N5 N4 -90.2(3) . . . . ? N3 Co1 N5 N4 -1.6(3) . . . . ? N9 Co1 N5 N4 92.0(3) . . . . ? N5 Co1 N6 C15 -32.7(9) . . . . ? N8 Co1 N6 C15 173.3(4) . . . . ? N11 Co1 N6 C15 80.8(4) . . . . ? N3 Co1 N6 C15 -8.4(4) . . . . ? N9 Co1 N6 C15 -101.5(4) . . . . ? N5 Co1 N6 C19 147.9(6) . . . . ? N8 Co1 N6 C19 -6.1(3) . . . . ? N11 Co1 N6 C19 -98.7(3) . . . . ? N3 Co1 N6 C19 172.2(3) . . . . ? N9 Co1 N6 C19 79.1(3) . . . . ? C22 N7 N8 C20 0.6(5) . . . . ? C19 N7 N8 C20 179.8(4) . . . . ? C22 N7 N8 Co1 169.8(3) . . . . ? C19 N7 N8 Co1 -11.0(5) . . . . ? N5 Co1 N8 C20 -2.7(6) . . . . ? N6 Co1 N8 C20 171.4(6) . . . . ? N11 Co1 N8 C20 -97.1(6) . . . . ? N3 Co1 N8 C20 162.8(6) . . . . ? N9 Co1 N8 C20 82.3(6) . . . . ? N5 Co1 N8 N7 -165.3(3) . . . . ? N6 Co1 N8 N7 8.8(3) . . . . ? N11 Co1 N8 N7 100.3(3) . . . . ? N3 Co1 N8 N7 0.2(9) . . . . ? N9 Co1 N8 N7 -80.3(3) . . . . ? N5 Co1 N9 C23 -116.6(3) . . . . ? N8 Co1 N9 C23 131.0(4) . . . . ? N6 Co1 N9 C23 51.6(3) . . . . ? N11 Co1 N9 C23 147(4) . . . . ? N3 Co1 N9 C23 -37.3(3) . . . . ? N5 Co1 N9 C27 60.5(4) . . . . ? N8 Co1 N9 C27 -51.8(4) . . . . ? N6 Co1 N9 C27 -131.3(4) . . . . ? N11 Co1 N9 C27 -36(4) . . . . ? N3 Co1 N9 C27 139.8(4) . . . . ? N5 Co1 N11 C33 121.6(8) . . . . ? N8 Co1 N11 C33 -126.3(8) . . . . ? N6 Co1 N11 C33 -46.8(9) . . . . ? N3 Co1 N11 C33 42.1(8) . . . . ? N9 Co1 N11 C33 -142(4) . . . . ? C15 N1 C1 C6 89.0(5) . . . . ? C7 N1 C1 C6 -90.2(5) . . . . ? C15 N1 C1 C2 -91.6(5) . . . . ? C7 N1 C1 C2 89.2(5) . . . . ? C6 C1 C2 C3 1.3(7) . . . . ? N1 C1 C2 C3 -178.0(4) . . . . ? C1 C2 C3 C4 0.4(7) . . . . ? C2 C3 C4 C5 -1.5(7) . . . . ? C2 C3 C4 N2 176.1(4) . . . . ? C25 N2 C4 C3 135.3(5) 6_565 . . . ? C30 N2 C4 C3 -41.6(6) . . . . ? C25 N2 C4 C5 -47.2(7) 6_565 . . . ? C30 N2 C4 C5 136.0(5) . . . . ? C3 C4 C5 C6 0.8(7) . . . . ? N2 C4 C5 C6 -176.7(4) . . . . ? C2 C1 C6 C5 -2.0(7) . . . . ? N1 C1 C6 C5 177.4(4) . . . . ? C4 C5 C6 C1 0.9(7) . . . . ? C11 N3 C7 C8 1.9(7) . . . . ? Co1 N3 C7 C8 176.3(4) . . . . ? C11 N3 C7 N1 -174.9(4) . . . . ? Co1 N3 C7 N1 -0.5(6) . . . . ? C15 N1 C7 N3 -18.7(7) . . . . ? C1 N1 C7 N3 160.4(4) . . . . ? C15 N1 C7 C8 164.5(5) . . . . ? C1 N1 C7 C8 -16.5(6) . . . . ? N3 C7 C8 C9 -1.7(8) . . . . ? N1 C7 C8 C9 175.1(5) . . . . ? C7 C8 C9 C10 0.4(8) . . . . ? C8 C9 C10 C11 0.5(8) . . . . ? C7 N3 C11 C10 -0.9(7) . . . . ? Co1 N3 C11 C10 -176.0(4) . . . . ? C7 N3 C11 N4 177.5(4) . . . . ? Co1 N3 C11 N4 2.3(5) . . . . ? C9 C10 C11 N3 -0.3(8) . . . . ? C9 C10 C11 N4 -178.6(4) . . . . ? C14 N4 C11 N3 177.3(4) . . . . ? N5 N4 C11 N3 -4.0(6) . . . . ? C14 N4 C11 C10 -4.3(7) . . . . ? N5 N4 C11 C10 174.5(4) . . . . ? N4 N5 C12 C13 0.6(5) . . . . ? Co1 N5 C12 C13 175.9(4) . . . . ? N5 C12 C13 C14 -0.5(6) . . . . ? N5 N4 C14 C13 0.2(6) . . . . ? C11 N4 C14 C13 179.1(5) . . . . ? C12 C13 C14 N4 0.2(6) . . . . ? C19 N6 C15 N1 176.2(4) . . . . ? Co1 N6 C15 N1 -3.3(6) . . . . ? C19 N6 C15 C16 -3.3(7) . . . . ? Co1 N6 C15 C16 177.3(3) . . . . ? C7 N1 C15 N6 20.9(8) . . . . ? C1 N1 C15 N6 -158.2(4) . . . . ? C7 N1 C15 C16 -159.7(5) . . . . ? C1 N1 C15 C16 21.3(6) . . . . ? N6 C15 C16 C17 3.2(7) . . . . ? N1 C15 C16 C17 -176.2(5) . . . . ? C15 C16 C17 C18 0.1(8) . . . . ? C16 C17 C18 C19 -3.1(8) . . . . ? C15 N6 C19 C18 0.0(7) . . . . ? Co1 N6 C19 C18 179.5(4) . . . . ? C15 N6 C19 N7 -177.3(4) . . . . ? Co1 N6 C19 N7 2.2(5) . . . . ? C17 C18 C19 N6 3.2(8) . . . . ? C17 C18 C19 N7 -179.6(5) . . . . ? C22 N7 C19 N6 -174.8(5) . . . . ? N8 N7 C19 N6 6.2(6) . . . . ? C22 N7 C19 C18 7.7(8) . . . . ? N8 N7 C19 C18 -171.3(4) . . . . ? N7 N8 C20 C21 -1.1(6) . . . . ? Co1 N8 C20 C21 -164.2(4) . . . . ? N8 C20 C21 C22 1.2(7) . . . . ? N8 N7 C22 C21 0.1(6) . . . . ? C19 N7 C22 C21 -179.0(5) . . . . ? C20 C21 C22 N7 -0.7(7) . . . . ? C27 N9 C23 C24 -1.8(6) . . . . ? Co1 N9 C23 C24 175.6(3) . . . . ? N9 C23 C24 C25 -0.1(7) . . . . ? C23 C24 C25 N2 -176.6(4) . . . 6_566 ? C23 C24 C25 C26 2.6(7) . . . . ? C24 C25 C26 C27 -3.3(7) . . . . ? N2 C25 C26 C27 176.0(5) 6_566 . . . ? C23 N9 C27 C26 1.1(7) . . . . ? Co1 N9 C27 C26 -176.2(4) . . . . ? C25 C26 C27 N9 1.5(8) . . . . ? C32 N10 C28 C29 0.6(9) . . . . ? N10 C28 C29 C30 0.4(9) . . . . ? C28 C29 C30 C31 -0.3(8) . . . . ? C28 C29 C30 N2 -179.4(4) . . . . ? C25 N2 C30 C29 -43.3(7) 6_565 . . . ? C4 N2 C30 C29 133.6(5) . . . . ? C25 N2 C30 C31 137.5(5) 6_565 . . . ? C4 N2 C30 C31 -45.5(6) . . . . ? C29 C30 C31 C32 -0.7(7) . . . . ? N2 C30 C31 C32 178.4(4) . . . . ? C28 N10 C32 C31 -1.7(9) . . . . ? C30 C31 C32 N10 1.9(8) . . . . ? Co1 N11 C33 S1 108(43) . . . . ? C35 N12 C34 O5 179.8(13) . . . . ? C36 N12 C34 O5 -0.9(19) . . . . ? C38 N13 C37 O6 0(8) . . . 2_656 ? C38 N13 C37 O6 180(8) 2_656 . . 2_656 ? C38 N13 C37 O6 180(8) . . . . ? C38 N13 C37 O6 0(8) 2_656 . . . ? C39' O6' C37' N13' -3(8) 2_656 . . . ? C39' O6' C37' C37' -41(16) 2_656 . . 2_656 ? C37' N13' C37' O6' -164(7) 2_656 . . . ? C39' N13' C37' O6' 2(6) 2_656 . . . ? C39' N13' C37' O6' -180(9) . . . . ? C38' N13' C37' O6' 117(95) 2_656 . . . ? C38' N13' C37' O6' 0(8) . . . . ? C39' N13' C37' C37' 166(8) 2_656 . . 2_656 ? C39' N13' C37' C37' -16(11) . . . 2_656 ? C38' N13' C37' C37' -79(96) 2_656 . . 2_656 ? C38' N13' C37' C37' 163(7) . . . 2_656 ? C37' N13' C37' C39' -166(8) 2_656 . . 2_656 ? C39' N13' C37' C39' 178(9) . . . 2_656 ? C38' N13' C37' C39' 115(97) 2_656 . . 2_656 ? C38' N13' C37' C39' -3(8) . . . 2_656 ? C37' N13' C38' C39' 76(97) 2_656 . . 2_656 ? C37' N13' C38' C39' 4(9) . . . 2_656 ? C39' N13' C38' C39' -177(9) . . . 2_656 ? C38' N13' C38' C39' -162(9) 2_656 . . 2_656 ? C37' N13' C38' C38' -122(95) 2_656 . . 2_656 ? C37' N13' C38' C38' 166(7) . . . 2_656 ? C39' N13' C38' C38' 162(9) 2_656 . . 2_656 ? C39' N13' C38' C38' -15(10) . . . 2_656 ? C37' N13' C39' O6' -3(7) 2_656 . . 2_656 ? C37' N13' C39' O6' 13(14) . . . 2_656 ? C39' N13' C39' O6' -176(9) 2_656 . . 2_656 ? C38' N13' C39' O6' 173(14) 2_656 . . 2_656 ? C38' N13' C39' O6' -167(10) . . . 2_656 ? C37' N13' C39' C38' -176(9) 2_656 . . 2_656 ? C37' N13' C39' C38' -161(6) . . . 2_656 ? C39' N13' C39' C38' 11(6) 2_656 . . 2_656 ? C38' N13' C39' C38' 20(13) . . . 2_656 ? C37' N13' C39' C37' 15(12) . . . 2_656 ? C39' N13' C39' C37' -173(5) 2_656 . . 2_656 ? C38' N13' C39' C37' 176(9) 2_656 . . 2_656 ? C38' N13' C39' C37' -164(6) . . . 2_656 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.633 _refine_diff_density_min -0.922 _refine_diff_density_rms 0.083 _database_code_depnum_ccdc_archive 'CCDC 968024' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_c2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C64 H48 Cl3 Cu2 N23 O12' _chemical_formula_weight 1564.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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 34.166(3) _cell_length_b 8.5280(9) _cell_length_c 24.721(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.831(2) _cell_angle_gamma 90.00 _cell_volume 7096.9(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5478 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 25.05 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3192 _exptl_absorpt_coefficient_mu 0.789 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8271 _exptl_absorpt_correction_T_max 0.9044 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'multiwire proportional' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20147 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 25.02 _reflns_number_total 6228 _reflns_number_gt 4804 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 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^)+(0.1196P)^2^+7.7541P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6228 _refine_ls_number_parameters 559 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_ref 0.1882 _refine_ls_wR_factor_gt 0.1777 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 Cu1 Cu 0.571356(13) 0.16805(5) 0.58057(2) 0.0364(2) Uani 1 1 d . . . Cl1 Cl 0.73809(4) 0.52618(14) 0.59509(5) 0.0540(3) Uani 1 1 d . . . Cl2 Cl 0.4884(5) 0.773(2) 0.7332(6) 0.091(5) Uani 0.287(13) 1 d P . 1 Cl2' Cl 0.4682(7) 0.836(2) 0.7164(8) 0.087(5) Uani 0.213(13) 1 d P . 2 N1 N 0.52300(10) 0.2432(4) 0.60752(14) 0.0416(8) Uani 1 1 d . . . N2 N 0.56915(9) 0.3782(4) 0.54692(12) 0.0319(7) Uani 1 1 d . . . N3 N 0.58017(9) -0.0417(4) 0.61386(13) 0.0363(7) Uani 1 1 d . . . N4 N 0.61911(9) 0.1130(3) 0.54925(12) 0.0306(7) Uani 1 1 d . . . N5 N 0.51951(10) 0.4013(4) 0.59934(14) 0.0410(8) Uani 1 1 d . . . N6 N 0.61436(9) -0.1053(4) 0.60241(12) 0.0326(7) Uani 1 1 d . . . N7 N 0.62020(10) 0.3409(4) 0.49293(13) 0.0386(8) Uani 1 1 d . . . N8 N 0.60719(11) 0.7193(4) 0.16514(14) 0.0450(8) Uani 1 1 d . . . N9 N 0.80462(13) 0.4948(7) 0.3144(2) 0.0724(13) Uani 1 1 d . . . N10 N 0.68117(11) 0.5554(5) 0.30804(14) 0.0514(10) Uani 1 1 d . . . N13 N 0.5000 0.0000 0.5000 0.086(2) Uani 1 2 d S . . N14 N 0.53047(15) 0.0721(6) 0.4909(3) 0.091(2) Uani 1 1 d . . . O1 O 0.74735(15) 0.6586(5) 0.5654(2) 0.1022(17) Uani 1 1 d . A . O2 O 0.69603(14) 0.5325(7) 0.5936(2) 0.090(2) Uani 0.942(12) 1 d P A 1 O3 O 0.7567(3) 0.5154(10) 0.6500(3) 0.146(3) Uani 0.942(12) 1 d P A 1 O4 O 0.74685(19) 0.3901(5) 0.5669(2) 0.086(2) Uani 0.942(12) 1 d P A 1 O5 O 0.478(3) 0.793(10) 0.675(4) 0.105(18) Uani 0.287(13) 1 d P . 1 O6 O 0.5000 0.93(13) 0.7500 0.15(10) Uani 0.57(3) 2 d SP . 1 O7 O 0.5230(12) 0.677(8) 0.744(6) 0.112(14) Uani 0.287(13) 1 d P . 1 O8 O 0.457(5) 0.696(15) 0.751(7) 0.11(3) Uani 0.287(13) 1 d P . 1 O2' O 0.772(3) 0.430(10) 0.606(4) 0.09(3) Uani 0.058(12) 1 d P A 2 O3' O 0.707(2) 0.443(9) 0.564(3) 0.08(3) Uani 0.058(12) 1 d P A 2 O4' O 0.727(3) 0.576(10) 0.644(4) 0.09(3) Uani 0.058(12) 1 d P A 2 O5' O 0.477(3) 0.826(13) 0.663(6) 0.084(19) Uani 0.213(13) 1 d P . 2 O6' O 0.5000 0.91(18) 0.7500 0.15(8) Uani 0.43(3) 2 d SP . 2 O7' O 0.4327(9) 0.930(4) 0.7114(12) 0.130(14) Uani 0.213(13) 1 d P . 2 O8' O 0.460(6) 0.684(18) 0.734(4) 0.10(3) Uani 0.213(13) 1 d P . 2 C1 C 0.78469(16) 0.6133(8) 0.2875(2) 0.0663(14) Uani 1 1 d . . . H1 H 0.7992 0.6849 0.2691 0.080 Uiso 1 1 calc R . . C2 C 0.74433(14) 0.6404(6) 0.28420(19) 0.0532(11) Uani 1 1 d . . . H2 H 0.7319 0.7286 0.2650 0.064 Uiso 1 1 calc R . . C3 C 0.72278(12) 0.5340(5) 0.30991(16) 0.0436(10) Uani 1 1 d . . . C4 C 0.74243(14) 0.4101(6) 0.33788(19) 0.0514(11) Uani 1 1 d . . . H4 H 0.7285 0.3353 0.3558 0.062 Uiso 1 1 calc R . . C5 C 0.78275(16) 0.3968(7) 0.3393(2) 0.0622(13) Uani 1 1 d . . . H5 H 0.7960 0.3119 0.3595 0.075 Uiso 1 1 calc R . . C6 C 0.65656(12) 0.6076(6) 0.26013(17) 0.0457(10) Uani 1 1 d . . . C7 C 0.66540(11) 0.5799(5) 0.20852(15) 0.0363(8) Uani 1 1 d . . . H7 H 0.6885 0.5224 0.2042 0.044 Uiso 1 1 calc R . . C8 C 0.63991(11) 0.6379(5) 0.16312(16) 0.0356(8) Uani 1 1 d . . . H8 H 0.6464 0.6175 0.1279 0.043 Uiso 1 1 calc R . . C9 C 0.59903(16) 0.7452(8) 0.21587(19) 0.0681(16) Uani 1 1 d . . . H9 H 0.5760 0.8047 0.2190 0.082 Uiso 1 1 calc R . . C10 C 0.62204(15) 0.6908(7) 0.2633(2) 0.0667(16) Uani 1 1 d . . . H10 H 0.6144 0.7100 0.2979 0.080 Uiso 1 1 calc R . . C11 C 0.66467(13) 0.5079(5) 0.35471(17) 0.0464(10) Uani 1 1 d . . . C12 C 0.63165(14) 0.4104(7) 0.34829(18) 0.0552(12) Uani 1 1 d . . . H12 H 0.6191 0.3806 0.3125 0.066 Uiso 1 1 calc R . . C13 C 0.68233(13) 0.5552(5) 0.40681(18) 0.0469(10) Uani 1 1 d . . . H13 H 0.7042 0.6256 0.4112 0.056 Uiso 1 1 calc R . . C14 C 0.59086(12) 0.4340(4) 0.51071(15) 0.0364(8) Uani 1 1 d . . . C15 C 0.58467(14) 0.5883(5) 0.49006(18) 0.0474(10) Uani 1 1 d . . . H15 H 0.6002 0.6283 0.4648 0.057 Uiso 1 1 calc R . . C16 C 0.55607(14) 0.6792(5) 0.50696(19) 0.0496(11) Uani 1 1 d . . . H16 H 0.5518 0.7830 0.4933 0.059 Uiso 1 1 calc R . . C17 C 0.53305(13) 0.6219(5) 0.54399(18) 0.0468(10) Uani 1 1 d . . . H17 H 0.5128 0.6831 0.5557 0.056 Uiso 1 1 calc R . . C18 C 0.54127(11) 0.4719(4) 0.56245(16) 0.0361(8) Uani 1 1 d . . . C19 C 0.63644(12) 0.1971(4) 0.51328(16) 0.0362(8) Uani 1 1 d . . . C20 C 0.67061(13) 0.1409(5) 0.49542(19) 0.0491(11) Uani 1 1 d . . . H20 H 0.6830 0.2009 0.4707 0.059 Uiso 1 1 calc R . . C21 C 0.68608(14) -0.0024(6) 0.5142(2) 0.0534(12) Uani 1 1 d . . . H21 H 0.7095 -0.0404 0.5027 0.064 Uiso 1 1 calc R . . C22 C 0.66787(13) -0.0908(5) 0.54939(18) 0.0461(10) Uani 1 1 d . . . H22 H 0.6776 -0.1914 0.5616 0.055 Uiso 1 1 calc R . . C23 C 0.63488(11) -0.0264(4) 0.56603(15) 0.0330(8) Uani 1 1 d . . . C24 C 0.62393(13) -0.2382(5) 0.63217(17) 0.0428(9) Uani 1 1 d . . . H24 H 0.6466 -0.3024 0.6318 0.051 Uiso 1 1 calc R . . C25 C 0.59457(14) -0.2615(5) 0.66268(18) 0.0491(11) Uani 1 1 d . . . H25 H 0.5924 -0.3459 0.6871 0.059 Uiso 1 1 calc R . . C26 C 0.56840(13) -0.1357(5) 0.65053(18) 0.0448(10) Uani 1 1 d . . . H26 H 0.5453 -0.1198 0.6664 0.054 Uiso 1 1 calc R . . C27 C 0.49853(14) 0.2060(6) 0.6426(2) 0.0593(13) Uani 1 1 d . . . H27 H 0.4944 0.1036 0.6556 0.071 Uiso 1 1 calc R . . C28 C 0.47992(18) 0.3444(7) 0.6570(3) 0.0738(16) Uani 1 1 d . . . H28 H 0.4614 0.3523 0.6816 0.089 Uiso 1 1 calc R . . C29 C 0.49351(15) 0.4637(6) 0.6290(2) 0.0621(13) Uani 1 1 d . . . H29 H 0.4862 0.5710 0.6300 0.074 Uiso 1 1 calc R . . C30 C 0.63561(12) 0.4013(5) 0.44551(16) 0.0398(9) Uani 1 1 d . . . C31 C 0.61683(14) 0.3562(6) 0.39359(18) 0.0501(11) Uani 1 1 d . . . H31 H 0.5942 0.2895 0.3892 0.060 Uiso 1 1 calc R . . C32 C 0.66827(13) 0.5003(5) 0.45226(17) 0.0457(10) Uani 1 1 d . . . H32 H 0.6809 0.5301 0.4880 0.055 Uiso 1 1 calc R . . 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 Cu1 0.0370(3) 0.0298(3) 0.0463(3) 0.00546(19) 0.0179(2) 0.00763(18) Cl1 0.0587(7) 0.0517(6) 0.0533(7) 0.0011(5) 0.0141(5) 0.0079(5) Cl2 0.097(12) 0.102(7) 0.090(9) -0.036(6) 0.059(7) -0.041(8) Cl2' 0.108(11) 0.082(8) 0.086(8) -0.036(6) 0.057(8) -0.040(7) N1 0.0363(18) 0.0410(19) 0.050(2) -0.0025(15) 0.0140(15) 0.0037(15) N2 0.0331(16) 0.0306(15) 0.0314(16) -0.0019(13) 0.0039(13) 0.0046(13) N3 0.0382(18) 0.0315(16) 0.0416(19) 0.0021(14) 0.0134(14) 0.0023(13) N4 0.0331(16) 0.0286(15) 0.0308(16) 0.0007(12) 0.0073(12) 0.0054(13) N5 0.0353(17) 0.0406(18) 0.048(2) -0.0086(15) 0.0098(15) 0.0083(14) N6 0.0340(16) 0.0293(15) 0.0353(17) 0.0033(13) 0.0084(13) 0.0045(13) N7 0.0445(19) 0.0392(18) 0.0345(18) 0.0109(13) 0.0140(14) 0.0080(14) N8 0.045(2) 0.055(2) 0.0345(19) 0.0092(16) 0.0073(15) 0.0108(17) N9 0.043(2) 0.104(4) 0.070(3) -0.015(3) 0.009(2) -0.003(3) N10 0.042(2) 0.076(3) 0.0370(19) 0.0252(18) 0.0098(15) 0.0073(18) N13 0.099(6) 0.062(4) 0.085(5) -0.022(4) -0.017(4) 0.030(5) N14 0.055(3) 0.059(3) 0.147(5) -0.045(3) -0.021(3) 0.004(2) O1 0.094(3) 0.065(3) 0.162(5) 0.018(3) 0.063(3) -0.010(2) O2 0.072(3) 0.099(4) 0.112(5) 0.030(4) 0.051(3) 0.014(3) O3 0.167(7) 0.157(6) 0.089(4) -0.023(4) -0.049(4) 0.044(6) O4 0.111(5) 0.063(3) 0.091(4) -0.009(2) 0.038(4) 0.015(3) O5 0.12(3) 0.11(5) 0.10(4) -0.02(3) 0.06(2) -0.01(3) O6 0.18(16) 0.14(18) 0.14(7) 0.000 0.02(4) 0.000 O7 0.12(4) 0.12(2) 0.11(3) -0.01(3) 0.04(4) -0.03(3) O8 0.12(6) 0.13(4) 0.11(5) -0.02(4) 0.07(5) -0.02(4) O2' 0.09(6) 0.08(5) 0.10(8) 0.01(5) 0.03(5) 0.03(5) O3' 0.08(6) 0.07(5) 0.08(5) 0.01(4) 0.02(4) 0.00(4) O4' 0.10(7) 0.08(5) 0.09(6) 0.00(4) 0.05(5) 0.01(5) O5' 0.09(3) 0.07(3) 0.11(5) -0.01(2) 0.07(3) -0.02(2) O6' 0.16(19) 0.1(3) 0.14(10) 0.000 0.02(6) 0.000 O7' 0.13(2) 0.14(3) 0.14(2) -0.060(19) 0.083(19) -0.005(19) O8' 0.11(6) 0.12(4) 0.10(5) -0.02(4) 0.05(5) -0.01(4) C1 0.051(3) 0.091(4) 0.057(3) 0.002(3) 0.006(2) -0.018(3) C2 0.044(3) 0.068(3) 0.045(3) 0.008(2) 0.0018(19) -0.009(2) C3 0.040(2) 0.060(3) 0.031(2) 0.0038(18) 0.0055(16) 0.0025(19) C4 0.051(3) 0.056(3) 0.048(3) 0.004(2) 0.011(2) 0.008(2) C5 0.055(3) 0.071(3) 0.057(3) -0.010(3) 0.000(2) 0.020(3) C6 0.041(2) 0.063(3) 0.034(2) 0.0149(19) 0.0078(17) 0.005(2) C7 0.0320(19) 0.041(2) 0.036(2) 0.0047(16) 0.0053(16) 0.0001(16) C8 0.036(2) 0.039(2) 0.031(2) 0.0009(16) 0.0052(15) -0.0025(16) C9 0.061(3) 0.105(4) 0.041(3) 0.016(3) 0.017(2) 0.037(3) C10 0.060(3) 0.107(4) 0.036(2) 0.019(3) 0.018(2) 0.035(3) C11 0.044(2) 0.061(3) 0.036(2) 0.0167(19) 0.0107(18) 0.004(2) C12 0.047(3) 0.082(3) 0.034(2) 0.012(2) 0.0016(19) -0.006(2) C13 0.043(2) 0.052(2) 0.045(2) 0.016(2) 0.0050(18) -0.0042(19) C14 0.041(2) 0.0351(19) 0.032(2) 0.0017(16) 0.0022(16) 0.0052(16) C15 0.054(3) 0.039(2) 0.048(3) 0.0092(18) 0.009(2) 0.0070(19) C16 0.057(3) 0.033(2) 0.055(3) 0.0056(18) 0.000(2) 0.0095(19) C17 0.049(2) 0.037(2) 0.051(3) -0.0061(19) -0.001(2) 0.0135(19) C18 0.037(2) 0.034(2) 0.035(2) -0.0074(16) 0.0000(16) 0.0042(16) C19 0.041(2) 0.037(2) 0.032(2) 0.0051(16) 0.0114(16) 0.0069(16) C20 0.048(3) 0.056(3) 0.050(3) 0.015(2) 0.026(2) 0.015(2) C21 0.049(3) 0.060(3) 0.058(3) 0.012(2) 0.028(2) 0.021(2) C22 0.051(3) 0.041(2) 0.049(2) 0.0122(19) 0.018(2) 0.0207(19) C23 0.036(2) 0.0332(19) 0.0301(19) 0.0038(15) 0.0064(15) 0.0051(15) C24 0.045(2) 0.039(2) 0.045(2) 0.0110(18) 0.0076(18) 0.0044(18) C25 0.059(3) 0.039(2) 0.052(3) 0.015(2) 0.017(2) 0.001(2) C26 0.047(2) 0.043(2) 0.047(2) 0.0070(18) 0.0189(19) 0.0008(19) C27 0.048(3) 0.064(3) 0.073(3) 0.002(3) 0.032(2) 0.003(2) C28 0.067(4) 0.077(4) 0.089(4) 0.002(3) 0.046(3) 0.014(3) C29 0.057(3) 0.062(3) 0.073(3) -0.011(3) 0.027(3) 0.019(2) C30 0.044(2) 0.044(2) 0.032(2) 0.0130(17) 0.0108(17) 0.0044(18) C31 0.046(2) 0.064(3) 0.039(2) 0.009(2) 0.0052(19) -0.006(2) C32 0.048(2) 0.052(2) 0.036(2) 0.0074(18) 0.0037(18) -0.004(2) _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 Cu1 N3 1.971(3) . ? Cu1 N2 1.972(3) . ? Cu1 N4 1.978(3) . ? Cu1 N1 1.990(3) . ? Cu1 N8 2.433(3) 6_566 ? Cu1 N14 2.546(5) . ? Cl1 O4' 1.40(7) . ? Cl1 O3' 1.40(8) . ? Cl1 O2' 1.40(8) . ? Cl1 O3 1.401(6) . ? Cl1 O1 1.412(4) . ? Cl1 O4 1.412(5) . ? Cl1 O2 1.432(5) . ? Cl2 Cl2 1.05(4) 2_656 ? Cl2 O7 1.11(9) 2_656 ? Cl2 O8 1.39(11) . ? Cl2 O7 1.43(6) . ? Cl2 O5 1.44(10) . ? Cl2 O6 1.4(11) . ? Cl2 O8 1.95(16) 2_656 ? Cl2' O6' 1.4(7) . ? Cl2' O5' 1.41(13) . ? Cl2' O8' 1.42(15) . ? Cl2' O7' 1.44(4) . ? N1 C27 1.341(6) . ? N1 N5 1.366(5) . ? N2 C14 1.344(5) . ? N2 C18 1.348(5) . ? N3 C26 1.323(5) . ? N3 N6 1.361(4) . ? N4 C23 1.341(5) . ? N4 C19 1.355(5) . ? N5 C29 1.354(5) . ? N5 C18 1.406(5) . ? N6 C24 1.360(5) . ? N6 C23 1.403(5) . ? N7 C19 1.403(5) . ? N7 C14 1.407(5) . ? N7 C30 1.459(5) . ? N8 C8 1.324(5) . ? N8 C9 1.349(6) . ? N8 Cu1 2.433(3) 6_565 ? N9 C1 1.331(8) . ? N9 C5 1.340(8) . ? N10 C6 1.403(5) . ? N10 C3 1.426(5) . ? N10 C11 1.426(5) . ? N13 N14 1.262(6) . ? N13 N14 1.262(6) 5_656 ? O6 Cl2 1.4(10) 2_656 ? O7 O8 0.69(17) 2_656 ? O7 Cl2 1.11(9) 2_656 ? O7 O7 1.66(15) 2_656 ? O8 O7 0.69(17) 2_656 ? O8 Cl2 1.95(16) 2_656 ? O6' Cl2' 1.4(7) 2_656 ? C1 C2 1.386(7) . ? C2 C3 1.389(6) . ? C3 C4 1.373(6) . ? C4 C5 1.376(7) . ? C6 C7 1.381(6) . ? C6 C10 1.390(6) . ? C7 C8 1.389(5) . ? C9 C10 1.376(7) . ? C11 C13 1.385(6) . ? C11 C12 1.389(6) . ? C12 C31 1.385(6) . ? C13 C32 1.377(6) . ? C14 C15 1.414(6) . ? C15 C16 1.368(6) . ? C16 C17 1.393(7) . ? C17 C18 1.371(6) . ? C19 C20 1.401(6) . ? C20 C21 1.380(6) . ? C21 C22 1.378(6) . ? C22 C23 1.379(5) . ? C24 C25 1.368(6) . ? C25 C26 1.396(6) . ? C27 C28 1.415(7) . ? C28 C29 1.357(8) . ? C30 C32 1.386(6) . ? C30 C31 1.388(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 Cu1 N2 173.39(13) . . ? N3 Cu1 N4 82.56(12) . . ? N2 Cu1 N4 91.45(12) . . ? N3 Cu1 N1 103.22(14) . . ? N2 Cu1 N1 82.79(13) . . ? N4 Cu1 N1 174.20(13) . . ? N3 Cu1 N8 88.91(13) . 6_566 ? N2 Cu1 N8 88.92(13) . 6_566 ? N4 Cu1 N8 95.88(12) . 6_566 ? N1 Cu1 N8 84.83(13) . 6_566 ? N3 Cu1 N14 95.39(17) . . ? N2 Cu1 N14 87.07(16) . . ? N4 Cu1 N14 87.10(16) . . ? N1 Cu1 N14 91.82(16) . . ? N8 Cu1 N14 175.07(14) 6_566 . ? O4' Cl1 O3' 109(5) . . ? O4' Cl1 O2' 111(6) . . ? O3' Cl1 O2' 109(5) . . ? O4' Cl1 O3 48(4) . . ? O3' Cl1 O3 133(3) . . ? O2' Cl1 O3 64(4) . . ? O4' Cl1 O1 109(3) . . ? O3' Cl1 O1 110(3) . . ? O2' Cl1 O1 108(4) . . ? O3 Cl1 O1 116.8(4) . . ? O4' Cl1 O4 142(3) . . ? O3' Cl1 O4 61(4) . . ? O2' Cl1 O4 51(5) . . ? O3 Cl1 O4 109.0(4) . . ? O1 Cl1 O4 108.4(3) . . ? O4' Cl1 O2 66(4) . . ? O3' Cl1 O2 48(4) . . ? O2' Cl1 O2 145(4) . . ? O3 Cl1 O2 108.3(4) . . ? O1 Cl1 O2 105.7(3) . . ? O4 Cl1 O2 108.4(4) . . ? Cl2 Cl2 O7 83(5) 2_656 2_656 ? Cl2 Cl2 O8 106(8) 2_656 . ? O7 Cl2 O8 30(8) 2_656 . ? Cl2 Cl2 O7 51(5) 2_656 . ? O7 Cl2 O7 81(7) 2_656 . ? O8 Cl2 O7 110(10) . . ? Cl2 Cl2 O5 146(4) 2_656 . ? O7 Cl2 O5 124(7) 2_656 . ? O8 Cl2 O5 107(9) . . ? O7 Cl2 O5 108(7) . . ? Cl2 Cl2 O6 69(10) 2_656 . ? O7 Cl2 O6 130(10) 2_656 . ? O8 Cl2 O6 123(5) . . ? O7 Cl2 O6 108(10) . . ? O5 Cl2 O6 101(10) . . ? Cl2 Cl2 O8 43(5) 2_656 2_656 ? O7 Cl2 O8 93(3) 2_656 2_656 ? O8 Cl2 O8 123(9) . 2_656 ? O7 Cl2 O8 15(5) . 2_656 ? O5 Cl2 O8 108(6) . 2_656 ? O6 Cl2 O8 93(10) . 2_656 ? O6' Cl2' O5' 108(7) . . ? O6' Cl2' O8' 114(10) . . ? O5' Cl2' O8' 108(6) . . ? O6' Cl2' O7' 111(10) . . ? O5' Cl2' O7' 106(5) . . ? O8' Cl2' O7' 108(9) . . ? C27 N1 N5 106.3(3) . . ? C27 N1 Cu1 141.7(3) . . ? N5 N1 Cu1 108.9(2) . . ? C14 N2 C18 118.5(3) . . ? C14 N2 Cu1 128.1(2) . . ? C18 N2 Cu1 113.4(3) . . ? C26 N3 N6 105.9(3) . . ? C26 N3 Cu1 142.5(3) . . ? N6 N3 Cu1 110.5(2) . . ? C23 N4 C19 118.4(3) . . ? C23 N4 Cu1 113.8(2) . . ? C19 N4 Cu1 127.8(2) . . ? C29 N5 N1 110.9(4) . . ? C29 N5 C18 130.7(4) . . ? N1 N5 C18 118.4(3) . . ? C24 N6 N3 110.8(3) . . ? C24 N6 C23 130.3(3) . . ? N3 N6 C23 118.9(3) . . ? C19 N7 C14 129.8(3) . . ? C19 N7 C30 115.0(3) . . ? C14 N7 C30 115.2(3) . . ? C8 N8 C9 115.5(4) . . ? C8 N8 Cu1 118.6(3) . 6_565 ? C9 N8 Cu1 125.5(3) . 6_565 ? C1 N9 C5 115.2(5) . . ? C6 N10 C3 121.2(3) . . ? C6 N10 C11 120.7(4) . . ? C3 N10 C11 117.8(3) . . ? N14 N13 N14 180.0(6) . 5_656 ? N13 N14 Cu1 110.3(4) . . ? Cl2 O6 Cl2 42(10) . 2_656 ? O8 O7 Cl2 98(10) 2_656 2_656 ? O8 O7 Cl2 131(10) 2_656 . ? Cl2 O7 Cl2 47(3) 2_656 . ? O8 O7 O7 153(10) 2_656 2_656 ? Cl2 O7 O7 58(7) 2_656 2_656 ? Cl2 O7 O7 41.4(17) . 2_656 ? O7 O8 Cl2 52(10) 2_656 . ? O7 O8 Cl2 33(10) 2_656 2_656 ? Cl2 O8 Cl2 31(4) . 2_656 ? Cl2' O6' Cl2' 126(10) 2_656 . ? N9 C1 C2 125.1(5) . . ? C1 C2 C3 117.7(5) . . ? C4 C3 C2 118.7(4) . . ? C4 C3 N10 120.9(4) . . ? C2 C3 N10 120.3(4) . . ? C3 C4 C5 118.5(5) . . ? N9 C5 C4 124.8(5) . . ? C7 C6 C10 117.5(4) . . ? C7 C6 N10 122.1(4) . . ? C10 C6 N10 120.4(4) . . ? C6 C7 C8 118.7(4) . . ? N8 C8 C7 125.0(4) . . ? N8 C9 C10 123.9(4) . . ? C9 C10 C6 119.4(4) . . ? C13 C11 C12 119.8(4) . . ? C13 C11 N10 120.0(4) . . ? C12 C11 N10 120.2(4) . . ? C31 C12 C11 120.6(4) . . ? C32 C13 C11 120.2(4) . . ? N2 C14 N7 120.8(3) . . ? N2 C14 C15 120.3(4) . . ? N7 C14 C15 118.9(4) . . ? C16 C15 C14 119.2(4) . . ? C15 C16 C17 121.0(4) . . ? C18 C17 C16 116.1(4) . . ? N2 C18 C17 124.9(4) . . ? N2 C18 N5 114.1(3) . . ? C17 C18 N5 120.9(4) . . ? N4 C19 C20 120.4(3) . . ? N4 C19 N7 120.5(3) . . ? C20 C19 N7 119.1(4) . . ? C21 C20 C19 119.3(4) . . ? C22 C21 C20 120.6(4) . . ? C21 C22 C23 116.8(4) . . ? N4 C23 C22 124.5(4) . . ? N4 C23 N6 113.9(3) . . ? C22 C23 N6 121.6(3) . . ? N6 C24 C25 106.8(4) . . ? C24 C25 C26 105.8(4) . . ? N3 C26 C25 110.8(4) . . ? N1 C27 C28 108.8(5) . . ? C29 C28 C27 106.8(5) . . ? N5 C29 C28 107.2(4) . . ? C32 C30 C31 121.0(4) . . ? C32 C30 N7 120.8(4) . . ? C31 C30 N7 118.2(4) . . ? C12 C31 C30 118.7(4) . . ? C13 C32 C30 119.6(4) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.523 _refine_diff_density_min -1.108 _refine_diff_density_rms 0.090 _database_code_depnum_ccdc_archive 'CCDC 968025'