# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Jing-Yuan Xu' _publ_contact_author_address ; School of Pharmaceutical Sciences Tianjin Medical University Tianjin 300070 CHINA ; _publ_contact_author_email JYXEM@YAHOO.COM.CN loop_ _publ_author_name 'Jing-Yuan Xu' 'Lan-Fang Hao' 'Dai-Zheng Liao' 'Cheng-Zhi Xie' ; Fei Xue ; 'Shi-Ping Yan' # Attachment 'complex_3_-_020831f.cif' data_020831f _database_code_depnum_ccdc_archive 'CCDC 761844' #TrackingRef 'complex_3_-_020831f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21.50 H20 Cl0.50 N6.50 Ni O5' _chemical_formula_weight 525.88 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' 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' Ni Ni 0.3393 1.1124 '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 18.016(6) _cell_length_b 14.677(5) _cell_length_c 19.305(7) _cell_angle_alpha 90.00 _cell_angle_beta 96.312(6) _cell_angle_gamma 90.00 _cell_volume 5074(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 24.99 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2168 _exptl_absorpt_coefficient_mu 0.861 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.876188 _exptl_absorpt_correction_T_max 1.000000 _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 9883 _diffrn_reflns_av_R_equivalents 0.0611 _diffrn_reflns_av_sigmaI/netI 0.0964 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4155 _reflns_number_gt 2243 _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^)+(0.1134P)^2^+1.9268P] 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 4155 _refine_ls_number_parameters 327 _refine_ls_number_restraints 157 _refine_ls_R_factor_all 0.1446 _refine_ls_R_factor_gt 0.0709 _refine_ls_wR_factor_ref 0.2129 _refine_ls_wR_factor_gt 0.1709 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.035 _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 Ni1 Ni 0.20688(5) 0.31118(6) 0.26678(4) 0.0463(3) Uani 1 1 d . . . N1 N 0.1507(3) 0.4241(4) 0.2972(2) 0.0428(13) Uani 1 1 d . . . N2 N 0.1490(3) 0.5754(4) 0.2987(3) 0.0547(15) Uani 1 1 d . . . H2A H 0.1634 0.6307 0.2938 0.066 Uiso 1 1 calc R . . N3 N 0.2951(3) 0.4084(5) 0.2803(3) 0.0607(17) Uani 1 1 d . . . H3B H 0.3302 0.3940 0.2516 0.073 Uiso 1 1 calc R . . N4 N 0.2590(4) 0.2648(5) 0.3591(3) 0.0613(17) Uani 1 1 d . . . N5 N 0.3536(4) 0.2820(7) 0.4418(4) 0.089(3) Uani 1 1 d . . . H5A H 0.3915 0.3063 0.4659 0.107 Uiso 1 1 calc R . . C1 C 0.0839(3) 0.4511(5) 0.3214(3) 0.0390(15) Uani 1 1 d . . . C2 C 0.0250(4) 0.4037(5) 0.3420(3) 0.0505(17) Uani 1 1 d . . . H2B H 0.0243 0.3403 0.3409 0.061 Uiso 1 1 calc R . . C3 C -0.0340(4) 0.4523(7) 0.3648(4) 0.062(2) Uani 1 1 d . . . H3A H -0.0737 0.4208 0.3805 0.075 Uiso 1 1 calc R . . C4 C -0.0348(4) 0.5452(7) 0.3648(4) 0.075(2) Uani 1 1 d . . . H4A H -0.0760 0.5754 0.3787 0.090 Uiso 1 1 calc R . . C5 C 0.0241(5) 0.5959(6) 0.3445(4) 0.069(2) Uani 1 1 d . . . H5B H 0.0243 0.6592 0.3458 0.082 Uiso 1 1 calc R . . C6 C 0.0824(4) 0.5465(5) 0.3223(3) 0.0510(18) Uani 1 1 d . . . C7 C 0.1859(4) 0.4992(5) 0.2853(3) 0.0475(17) Uani 1 1 d . . . C8 C 0.2610(4) 0.4979(6) 0.2588(4) 0.063(2) Uani 1 1 d . . . H8A H 0.2558 0.5038 0.2084 0.076 Uiso 1 1 calc R . . H8B H 0.2917 0.5475 0.2789 0.076 Uiso 1 1 calc R . . C9 C 0.3293(4) 0.4054(7) 0.3534(4) 0.078(3) Uani 1 1 d . . . H9A H 0.3827 0.4154 0.3551 0.093 Uiso 1 1 calc R . . H9B H 0.3085 0.4533 0.3799 0.093 Uiso 1 1 calc R . . C10 C 0.3152(5) 0.3167(8) 0.3839(4) 0.073(3) Uani 1 1 d . . . C11 C 0.3211(6) 0.2019(9) 0.4546(4) 0.082(3) Uani 1 1 d . . . C12 C 0.3380(8) 0.1369(11) 0.5067(5) 0.113(5) Uani 1 1 d . . . H12A H 0.3774 0.1441 0.5417 0.136 Uiso 1 1 calc R . . C13 C 0.2927(11) 0.0620(12) 0.5028(6) 0.142(7) Uani 1 1 d . . . H13A H 0.3033 0.0170 0.5363 0.171 Uiso 1 1 calc R . . C14 C 0.2309(7) 0.0470(8) 0.4521(5) 0.107(4) Uani 1 1 d . . . H14A H 0.2018 -0.0052 0.4526 0.129 Uiso 1 1 calc R . . C15 C 0.2158(6) 0.1143(8) 0.4014(4) 0.085(3) Uani 1 1 d . . . H15A H 0.1756 0.1084 0.3671 0.102 Uiso 1 1 calc R . . C16 C 0.2621(5) 0.1905(7) 0.4032(3) 0.065(2) Uani 1 1 d . . . N6 N 0.1203(4) 0.2215(4) 0.2585(3) 0.0622(15) Uani 1 1 d U . . C17 C 0.0648(5) 0.1933(6) 0.2531(5) 0.0751(18) Uani 1 1 d U . . N7 N 0.0000 0.1492(7) 0.2500 0.100(3) Uani 1 2 d SU . . O1 O 0.1904(3) 0.3434(3) 0.1600(2) 0.0602(13) Uani 1 1 d U . . O2 O 0.2664(3) 0.2325(4) 0.1928(2) 0.0590(12) Uani 1 1 d U . . C18 C 0.2333(4) 0.2825(5) 0.1457(3) 0.0552(14) Uani 1 1 d U . . C19 C 0.2434(4) 0.2660(5) 0.0695(3) 0.0545(14) Uani 1 1 d U . . C20 C 0.2938(4) 0.2041(6) 0.0502(3) 0.0663(18) Uani 1 1 d U . . H20A H 0.3234 0.1715 0.0841 0.080 Uiso 1 1 calc R . . C21 C 0.1991(5) 0.3102(6) 0.0199(3) 0.0652(18) Uani 1 1 d U . . H21A H 0.1634 0.3508 0.0326 0.078 Uiso 1 1 calc R . . O3 O 0.4754(7) 0.6292(12) 0.0201(9) 0.138(5) Uani 0.50 1 d PDU . . H3 H 0.4866 0.5750 0.0227 0.166 Uiso 0.50 1 calc PR . . C22 C 0.5412(11) 0.6836(18) 0.0374(16) 0.149(7) Uani 0.50 1 d PDU . . H22A H 0.5736 0.6777 0.0014 0.179 Uiso 0.50 1 calc PR . . H22B H 0.5668 0.6632 0.0809 0.179 Uiso 0.50 1 calc PR . . H22C H 0.5271 0.7463 0.0415 0.179 Uiso 0.50 1 calc PR . . O1W O 0.4718(13) 0.5073(14) 0.1135(12) 0.202(10) Uani 0.50 1 d PU . . H1WA H 0.5122 0.5421 0.1112 0.303 Uiso 0.50 1 d PR . . H1WB H 0.4673 0.4492 0.0846 0.303 Uiso 0.50 1 d PR . . Cl1 Cl 0.5000 0.3498(6) 0.2500 0.316(7) Uani 1 2 d SDU . . O4 O 0.4559(7) 0.4078(7) 0.2015(5) 0.359(8) Uani 1 1 d DU . . O5 O 0.4521(6) 0.2952(7) 0.2858(7) 0.341(8) Uani 1 1 d DU . . 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 Ni1 0.0442(5) 0.0647(6) 0.0305(4) -0.0046(4) 0.0063(3) 0.0134(4) N1 0.045(3) 0.053(4) 0.031(2) -0.007(2) 0.005(2) -0.006(3) N2 0.067(4) 0.048(4) 0.051(3) 0.001(3) 0.011(3) -0.013(3) N3 0.041(3) 0.091(5) 0.054(3) -0.010(3) 0.020(3) 0.006(3) N4 0.052(4) 0.094(5) 0.036(3) -0.003(3) -0.001(3) 0.019(4) N5 0.072(5) 0.138(8) 0.052(4) -0.020(5) -0.016(4) 0.037(5) C1 0.036(4) 0.051(5) 0.029(3) -0.008(3) 0.001(3) -0.003(3) C2 0.056(5) 0.055(5) 0.040(3) -0.008(3) 0.005(3) -0.011(4) C3 0.036(4) 0.099(7) 0.052(4) -0.016(4) 0.008(3) -0.003(4) C4 0.052(5) 0.096(8) 0.080(5) -0.028(5) 0.020(4) 0.014(5) C5 0.066(5) 0.061(5) 0.078(5) -0.020(4) 0.008(4) 0.012(4) C6 0.041(4) 0.073(6) 0.040(3) -0.006(3) 0.005(3) 0.001(4) C7 0.046(4) 0.063(5) 0.034(3) 0.004(3) 0.008(3) -0.002(4) C8 0.058(5) 0.077(6) 0.060(4) -0.002(4) 0.028(4) -0.020(4) C9 0.041(5) 0.123(9) 0.068(5) -0.021(5) -0.002(4) 0.002(5) C10 0.057(5) 0.120(8) 0.043(4) -0.009(5) 0.002(4) 0.036(6) C11 0.090(7) 0.119(8) 0.037(4) -0.006(5) 0.001(4) 0.050(7) C12 0.128(11) 0.161(12) 0.047(5) -0.001(7) -0.003(6) 0.076(10) C13 0.215(17) 0.164(14) 0.051(6) 0.019(8) 0.030(9) 0.114(13) C14 0.155(10) 0.117(9) 0.053(5) 0.015(5) 0.027(6) 0.065(8) C15 0.119(8) 0.100(8) 0.037(4) 0.002(4) 0.016(4) 0.052(7) C16 0.084(6) 0.082(6) 0.031(4) -0.006(4) 0.010(4) 0.043(5) N6 0.052(4) 0.053(4) 0.081(4) -0.006(3) 0.001(3) 0.006(3) C17 0.062(4) 0.047(4) 0.114(4) -0.003(3) -0.002(4) 0.005(3) N7 0.081(5) 0.064(5) 0.152(6) 0.000 0.000(5) 0.000 O1 0.074(3) 0.075(3) 0.033(2) -0.004(2) 0.011(2) 0.034(2) O2 0.065(3) 0.082(3) 0.031(2) -0.001(2) 0.009(2) 0.033(2) C18 0.064(3) 0.074(3) 0.030(2) -0.003(2) 0.012(2) 0.030(3) C19 0.065(3) 0.071(3) 0.029(2) 0.000(2) 0.011(2) 0.033(3) C20 0.074(4) 0.087(4) 0.038(3) 0.006(3) 0.005(3) 0.040(3) C21 0.079(4) 0.080(4) 0.038(3) -0.003(3) 0.013(3) 0.041(4) O3 0.071(8) 0.176(14) 0.157(12) 0.018(11) -0.036(8) 0.000(9) C22 0.088(11) 0.183(16) 0.169(14) 0.008(13) -0.023(11) 0.001(11) O1W 0.25(2) 0.116(16) 0.23(2) -0.001(15) -0.01(2) 0.079(16) Cl1 0.256(11) 0.150(8) 0.58(2) 0.000 0.200(12) 0.000 O4 0.281(14) 0.217(13) 0.60(2) 0.006(10) 0.165(14) -0.003(9) O5 0.272(14) 0.189(11) 0.60(2) 0.029(9) 0.205(14) -0.001(8) _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 Ni1 N6 2.034(7) . ? Ni1 N4 2.038(6) . ? Ni1 N1 2.061(5) . ? Ni1 O1 2.104(4) . ? Ni1 N3 2.130(6) . ? Ni1 O2 2.203(4) . ? Ni1 C18 2.473(6) . ? N1 C7 1.304(8) . ? N1 C1 1.395(7) . ? N2 C7 1.341(9) . ? N2 C6 1.394(8) . ? N2 H2A 0.8600 . ? N3 C9 1.477(9) . ? N3 C8 1.489(10) . ? N3 H3B 0.9100 . ? N4 C10 1.314(11) . ? N4 C16 1.381(11) . ? N5 C10 1.348(10) . ? N5 C11 1.349(12) . ? N5 H5A 0.8600 . ? C1 C2 1.365(8) . ? C1 C6 1.401(10) . ? C2 C3 1.392(9) . ? C2 H2B 0.9300 . ? C3 C4 1.363(12) . ? C3 H3A 0.9300 . ? C4 C5 1.387(11) . ? C4 H4A 0.9300 . ? C5 C6 1.383(10) . ? C5 H5B 0.9300 . ? C7 C8 1.499(9) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.463(13) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C16 1.382(12) . ? C11 C12 1.395(15) . ? C12 C13 1.367(19) . ? C12 H12A 0.9300 . ? C13 C14 1.416(19) . ? C13 H13A 0.9300 . ? C14 C15 1.396(13) . ? C14 H14A 0.9300 . ? C15 C16 1.393(13) . ? C15 H15A 0.9300 . ? N6 C17 1.075(9) . ? C17 N7 1.331(11) . ? N7 C17 1.331(11) 2 ? O1 C18 1.233(7) . ? O2 C18 1.266(8) . ? C18 C19 1.521(8) . ? C19 C21 1.344(10) . ? C19 C20 1.363(9) . ? C20 C21 1.390(9) 7 ? C20 H20A 0.9300 . ? C21 C20 1.390(9) 7 ? C21 H21A 0.9300 . ? O3 C22 1.438(5) . ? O3 H3 0.8200 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? O1W H1WA 0.8944 . ? O1W H1WB 1.0169 . ? Cl1 O5 1.411(4) . ? Cl1 O5 1.411(4) 2_655 ? Cl1 O4 1.438(4) 2_655 ? Cl1 O4 1.438(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N6 Ni1 N4 97.4(3) . . ? N6 Ni1 N1 98.4(2) . . ? N4 Ni1 N1 102.3(2) . . ? N6 Ni1 O1 92.5(2) . . ? N4 Ni1 O1 159.0(2) . . ? N1 Ni1 O1 94.48(18) . . ? N6 Ni1 N3 176.8(2) . . ? N4 Ni1 N3 81.4(3) . . ? N1 Ni1 N3 79.0(2) . . ? O1 Ni1 N3 89.6(2) . . ? N6 Ni1 O2 91.9(2) . . ? N4 Ni1 O2 100.4(2) . . ? N1 Ni1 O2 153.53(19) . . ? O1 Ni1 O2 60.60(17) . . ? N3 Ni1 O2 91.2(2) . . ? N6 Ni1 C18 92.4(3) . . ? N4 Ni1 C18 130.7(2) . . ? N1 Ni1 C18 123.9(2) . . ? O1 Ni1 C18 29.88(19) . . ? N3 Ni1 C18 90.7(2) . . ? O2 Ni1 C18 30.72(19) . . ? C7 N1 C1 105.8(5) . . ? C7 N1 Ni1 111.5(4) . . ? C1 N1 Ni1 142.4(4) . . ? C7 N2 C6 105.8(6) . . ? C7 N2 H2A 127.1 . . ? C6 N2 H2A 127.1 . . ? C9 N3 C8 114.2(6) . . ? C9 N3 Ni1 108.9(5) . . ? C8 N3 Ni1 106.1(4) . . ? C9 N3 H3B 109.2 . . ? C8 N3 H3B 109.2 . . ? Ni1 N3 H3B 109.2 . . ? C10 N4 C16 104.8(7) . . ? C10 N4 Ni1 112.8(6) . . ? C16 N4 Ni1 141.8(6) . . ? C10 N5 C11 106.7(8) . . ? C10 N5 H5A 126.7 . . ? C11 N5 H5A 126.7 . . ? C2 C1 N1 132.8(6) . . ? C2 C1 C6 119.3(6) . . ? N1 C1 C6 107.8(6) . . ? C1 C2 C3 118.4(7) . . ? C1 C2 H2B 120.8 . . ? C3 C2 H2B 120.8 . . ? C4 C3 C2 121.5(7) . . ? C4 C3 H3A 119.3 . . ? C2 C3 H3A 119.3 . . ? C3 C4 C5 121.9(7) . . ? C3 C4 H4A 119.1 . . ? C5 C4 H4A 119.1 . . ? C6 C5 C4 115.9(8) . . ? C6 C5 H5B 122.0 . . ? C4 C5 H5B 122.0 . . ? C5 C6 N2 130.7(8) . . ? C5 C6 C1 122.9(7) . . ? N2 C6 C1 106.4(6) . . ? N1 C7 N2 114.2(6) . . ? N1 C7 C8 121.6(7) . . ? N2 C7 C8 124.2(7) . . ? N3 C8 C7 106.0(6) . . ? N3 C8 H8A 110.5 . . ? C7 C8 H8A 110.5 . . ? N3 C8 H8B 110.5 . . ? C7 C8 H8B 110.5 . . ? H8A C8 H8B 108.7 . . ? C10 C9 N3 109.8(7) . . ? C10 C9 H9A 109.7 . . ? N3 C9 H9A 109.7 . . ? C10 C9 H9B 109.7 . . ? N3 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? N4 C10 N5 112.9(10) . . ? N4 C10 C9 122.0(7) . . ? N5 C10 C9 125.0(9) . . ? N5 C11 C16 106.8(8) . . ? N5 C11 C12 131.6(11) . . ? C16 C11 C12 121.6(12) . . ? C13 C12 C11 115.4(12) . . ? C13 C12 H12A 122.3 . . ? C11 C12 H12A 122.3 . . ? C12 C13 C14 125.7(12) . . ? C12 C13 H13A 117.2 . . ? C14 C13 H13A 117.2 . . ? C15 C14 C13 116.9(13) . . ? C15 C14 H14A 121.6 . . ? C13 C14 H14A 121.6 . . ? C16 C15 C14 118.7(10) . . ? C16 C15 H15A 120.6 . . ? C14 C15 H15A 120.6 . . ? N4 C16 C11 108.8(9) . . ? N4 C16 C15 129.4(8) . . ? C11 C16 C15 121.8(9) . . ? C17 N6 Ni1 162.3(7) . . ? N6 C17 N7 172.9(10) . . ? C17 N7 C17 121.7(11) 2 . ? C18 O1 Ni1 91.9(4) . . ? C18 O2 Ni1 86.5(4) . . ? O1 C18 O2 121.0(5) . . ? O1 C18 C19 118.5(6) . . ? O2 C18 C19 120.4(6) . . ? O1 C18 Ni1 58.2(3) . . ? O2 C18 Ni1 62.8(3) . . ? C19 C18 Ni1 175.8(5) . . ? C21 C19 C20 119.3(6) . . ? C21 C19 C18 119.1(6) . . ? C20 C19 C18 121.6(6) . . ? C19 C20 C21 120.1(6) . 7 ? C19 C20 H20A 119.9 . . ? C21 C20 H20A 119.9 7 . ? C19 C21 C20 120.6(7) . 7 ? C19 C21 H21A 119.7 . . ? C20 C21 H21A 119.7 7 . ? C22 O3 H3 109.5 . . ? O3 C22 H22A 109.5 . . ? O3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? H1WA O1W H1WB 117.9 . . ? O5 Cl1 O5 110.9(5) . 2_655 ? O5 Cl1 O4 110.0(3) . 2_655 ? O5 Cl1 O4 109.3(3) 2_655 2_655 ? O5 Cl1 O4 109.3(3) . . ? O5 Cl1 O4 110.0(3) 2_655 . ? O4 Cl1 O4 107.3(5) 2_655 . ? 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 N6 Ni1 N1 C7 -159.6(4) . . . . ? N4 Ni1 N1 C7 100.9(4) . . . . ? O1 Ni1 N1 C7 -66.3(4) . . . . ? N3 Ni1 N1 C7 22.3(4) . . . . ? O2 Ni1 N1 C7 -47.6(6) . . . . ? C18 Ni1 N1 C7 -61.0(5) . . . . ? N6 Ni1 N1 C1 12.8(6) . . . . ? N4 Ni1 N1 C1 -86.7(6) . . . . ? O1 Ni1 N1 C1 106.0(6) . . . . ? N3 Ni1 N1 C1 -165.3(6) . . . . ? O2 Ni1 N1 C1 124.7(6) . . . . ? C18 Ni1 N1 C1 111.4(6) . . . . ? N6 Ni1 N3 C9 52(5) . . . . ? N4 Ni1 N3 C9 -15.6(5) . . . . ? N1 Ni1 N3 C9 88.8(5) . . . . ? O1 Ni1 N3 C9 -176.6(5) . . . . ? O2 Ni1 N3 C9 -116.0(5) . . . . ? C18 Ni1 N3 C9 -146.7(5) . . . . ? N6 Ni1 N3 C8 -71(5) . . . . ? N4 Ni1 N3 C8 -138.9(4) . . . . ? N1 Ni1 N3 C8 -34.5(4) . . . . ? O1 Ni1 N3 C8 60.1(4) . . . . ? O2 Ni1 N3 C8 120.7(4) . . . . ? C18 Ni1 N3 C8 90.0(4) . . . . ? N6 Ni1 N4 C10 -172.9(5) . . . . ? N1 Ni1 N4 C10 -72.6(5) . . . . ? O1 Ni1 N4 C10 69.6(9) . . . . ? N3 Ni1 N4 C10 4.1(5) . . . . ? O2 Ni1 N4 C10 93.8(5) . . . . ? C18 Ni1 N4 C10 87.6(6) . . . . ? N6 Ni1 N4 C16 17.3(8) . . . . ? N1 Ni1 N4 C16 117.6(8) . . . . ? O1 Ni1 N4 C16 -100.2(10) . . . . ? N3 Ni1 N4 C16 -165.7(8) . . . . ? O2 Ni1 N4 C16 -76.1(8) . . . . ? C18 Ni1 N4 C16 -82.3(8) . . . . ? C7 N1 C1 C2 -180.0(6) . . . . ? Ni1 N1 C1 C2 7.4(10) . . . . ? C7 N1 C1 C6 0.3(6) . . . . ? Ni1 N1 C1 C6 -172.3(5) . . . . ? N1 C1 C2 C3 179.0(6) . . . . ? C6 C1 C2 C3 -1.4(9) . . . . ? C1 C2 C3 C4 2.0(10) . . . . ? C2 C3 C4 C5 -2.4(12) . . . . ? C3 C4 C5 C6 2.0(12) . . . . ? C4 C5 C6 N2 180.0(7) . . . . ? C4 C5 C6 C1 -1.4(10) . . . . ? C7 N2 C6 C5 178.8(7) . . . . ? C7 N2 C6 C1 0.0(6) . . . . ? C2 C1 C6 C5 1.2(9) . . . . ? N1 C1 C6 C5 -179.1(6) . . . . ? C2 C1 C6 N2 -179.9(5) . . . . ? N1 C1 C6 N2 -0.2(6) . . . . ? C1 N1 C7 N2 -0.4(7) . . . . ? Ni1 N1 C7 N2 174.8(4) . . . . ? C1 N1 C7 C8 179.7(6) . . . . ? Ni1 N1 C7 C8 -5.1(7) . . . . ? C6 N2 C7 N1 0.3(7) . . . . ? C6 N2 C7 C8 -179.9(6) . . . . ? C9 N3 C8 C7 -80.7(7) . . . . ? Ni1 N3 C8 C7 39.2(6) . . . . ? N1 C7 C8 N3 -24.4(8) . . . . ? N2 C7 C8 N3 155.7(6) . . . . ? C8 N3 C9 C10 141.7(6) . . . . ? Ni1 N3 C9 C10 23.3(7) . . . . ? C16 N4 C10 N5 -1.2(8) . . . . ? Ni1 N4 C10 N5 -174.7(5) . . . . ? C16 N4 C10 C9 -177.0(7) . . . . ? Ni1 N4 C10 C9 9.5(9) . . . . ? C11 N5 C10 N4 1.2(9) . . . . ? C11 N5 C10 C9 176.8(7) . . . . ? N3 C9 C10 N4 -23.0(10) . . . . ? N3 C9 C10 N5 161.7(7) . . . . ? C10 N5 C11 C16 -0.6(9) . . . . ? C10 N5 C11 C12 179.0(9) . . . . ? N5 C11 C12 C13 -179.2(10) . . . . ? C16 C11 C12 C13 0.3(15) . . . . ? C11 C12 C13 C14 -1.3(19) . . . . ? C12 C13 C14 C15 0.8(17) . . . . ? C13 C14 C15 C16 0.7(12) . . . . ? C10 N4 C16 C11 0.8(8) . . . . ? Ni1 N4 C16 C11 171.1(6) . . . . ? C10 N4 C16 C15 179.9(7) . . . . ? Ni1 N4 C16 C15 -9.8(13) . . . . ? N5 C11 C16 N4 -0.2(8) . . . . ? C12 C11 C16 N4 -179.8(8) . . . . ? N5 C11 C16 C15 -179.3(7) . . . . ? C12 C11 C16 C15 1.1(12) . . . . ? C14 C15 C16 N4 179.5(7) . . . . ? C14 C15 C16 C11 -1.6(11) . . . . ? N4 Ni1 N6 C17 124(3) . . . . ? N1 Ni1 N6 C17 20(3) . . . . ? O1 Ni1 N6 C17 -75(3) . . . . ? N3 Ni1 N6 C17 57(6) . . . . ? O2 Ni1 N6 C17 -135(3) . . . . ? C18 Ni1 N6 C17 -105(3) . . . . ? Ni1 N6 C17 N7 -158(6) . . . . ? N6 C17 N7 C17 156(9) . . . 2 ? N6 Ni1 O1 C18 -90.3(5) . . . . ? N4 Ni1 O1 C18 28.0(9) . . . . ? N1 Ni1 O1 C18 171.1(5) . . . . ? N3 Ni1 O1 C18 92.1(5) . . . . ? O2 Ni1 O1 C18 0.5(4) . . . . ? N6 Ni1 O2 C18 91.4(5) . . . . ? N4 Ni1 O2 C18 -170.8(5) . . . . ? N1 Ni1 O2 C18 -22.0(7) . . . . ? O1 Ni1 O2 C18 -0.5(4) . . . . ? N3 Ni1 O2 C18 -89.3(5) . . . . ? Ni1 O1 C18 O2 -0.9(8) . . . . ? Ni1 O1 C18 C19 176.9(7) . . . . ? Ni1 O2 C18 O1 0.8(7) . . . . ? Ni1 O2 C18 C19 -176.9(7) . . . . ? N6 Ni1 C18 O1 91.0(5) . . . . ? N4 Ni1 C18 O1 -167.2(4) . . . . ? N1 Ni1 C18 O1 -10.8(6) . . . . ? N3 Ni1 C18 O1 -88.0(5) . . . . ? O2 Ni1 C18 O1 -179.2(7) . . . . ? N6 Ni1 C18 O2 -89.8(5) . . . . ? N4 Ni1 C18 O2 12.0(6) . . . . ? N1 Ni1 C18 O2 168.4(4) . . . . ? O1 Ni1 C18 O2 179.2(7) . . . . ? N3 Ni1 C18 O2 91.2(5) . . . . ? N6 Ni1 C18 C19 50(8) . . . . ? N4 Ni1 C18 C19 152(8) . . . . ? N1 Ni1 C18 C19 -52(8) . . . . ? O1 Ni1 C18 C19 -41(8) . . . . ? N3 Ni1 C18 C19 -129(8) . . . . ? O2 Ni1 C18 C19 140(8) . . . . ? O1 C18 C19 C21 -8.0(12) . . . . ? O2 C18 C19 C21 169.8(8) . . . . ? Ni1 C18 C19 C21 31(8) . . . . ? O1 C18 C19 C20 175.3(8) . . . . ? O2 C18 C19 C20 -6.9(12) . . . . ? Ni1 C18 C19 C20 -145(7) . . . . ? C21 C19 C20 C21 2.4(15) . . . 7 ? C18 C19 C20 C21 179.1(8) . . . 7 ? C20 C19 C21 C20 -2.4(15) . . . 7 ? C18 C19 C21 C20 -179.2(8) . . . 7 ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.888 _refine_diff_density_min -0.824 _refine_diff_density_rms 0.081 # Attachment 'complex_4_-_020914g.cif' data_020914g _database_code_depnum_ccdc_archive 'CCDC 761845' #TrackingRef 'complex_4_-_020914g.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21.50 H19 Cl0.50 N6.50 O4.50 Zn' _chemical_formula_weight 523.53 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' 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 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 18.402(7) _cell_length_b 14.251(5) _cell_length_c 18.889(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.502(7) _cell_angle_gamma 90.00 _cell_volume 4938(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 849 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 19.12 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2144 _exptl_absorpt_coefficient_mu 1.091 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7798 _exptl_absorpt_correction_T_max 0.8114 _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_reflns_number 8245 _diffrn_reflns_av_R_equivalents 0.0864 _diffrn_reflns_av_sigmaI/netI 0.1354 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4138 _reflns_number_gt 1647 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.1072P)^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 4138 _refine_ls_number_parameters 361 _refine_ls_number_restraints 105 _refine_ls_R_factor_all 0.1977 _refine_ls_R_factor_gt 0.0726 _refine_ls_wR_factor_ref 0.2159 _refine_ls_wR_factor_gt 0.1621 _refine_ls_goodness_of_fit_ref 0.923 _refine_ls_restrained_S_all 0.921 _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 0.19451(5) 0.80939(7) 0.28065(4) 0.0772(4) Uani 1 1 d . . . N1 N 0.2856(4) 0.9189(6) 0.2898(4) 0.094(2) Uani 1 1 d . . . H1A H 0.3190 0.9055 0.2582 0.112 Uiso 1 1 calc R . . N2 N 0.1389(4) 0.9282(5) 0.3047(3) 0.0687(18) Uani 1 1 d . . . N3 N 0.1344(4) 1.0831(5) 0.3101(3) 0.0796(19) Uani 1 1 d . . . H3A H 0.1479 1.1408 0.3087 0.096 Uiso 1 1 calc R . . N4 N 0.2582(4) 0.7618(6) 0.3658(3) 0.0730(19) Uani 1 1 d . . . N5 N 0.3502(5) 0.7783(9) 0.4454(5) 0.113(3) Uani 1 1 d . . . H5B H 0.3870 0.8039 0.4688 0.135 Uiso 1 1 calc R . . C1 C 0.2525(5) 1.0075(9) 0.2727(5) 0.098(3) Uani 1 1 d . . . H1B H 0.2521 1.0187 0.2220 0.118 Uiso 1 1 calc R . . H1C H 0.2803 1.0572 0.2972 0.118 Uiso 1 1 calc R . . C2 C 0.1744(5) 1.0071(8) 0.2952(4) 0.074(2) Uani 1 1 d . . . C3 C 0.0715(4) 0.9560(7) 0.3257(3) 0.060(2) Uani 1 1 d . . . C4 C 0.0115(4) 0.9027(7) 0.3423(4) 0.074(2) Uani 1 1 d . . . H4A H 0.0120 0.8374 0.3408 0.089 Uiso 1 1 calc R . . C5 C -0.0483(5) 0.9520(11) 0.3610(4) 0.096(3) Uani 1 1 d . . . H5A H -0.0888 0.9185 0.3735 0.115 Uiso 1 1 calc R . . C6 C -0.0513(6) 1.0470(11) 0.3621(5) 0.101(3) Uani 1 1 d . . . H6A H -0.0939 1.0769 0.3731 0.122 Uiso 1 1 calc R . . C7 C 0.0061(6) 1.0975(8) 0.3476(5) 0.096(3) Uani 1 1 d . . . H7A H 0.0051 1.1627 0.3506 0.116 Uiso 1 1 calc R . . C8 C 0.0685(5) 1.0509(8) 0.3276(4) 0.074(2) Uani 1 1 d . . . C9 C 0.3197(5) 0.9134(8) 0.3616(5) 0.095(3) Uani 1 1 d . . . H9A H 0.2973 0.9584 0.3917 0.114 Uiso 1 1 calc R . . H9B H 0.3711 0.9283 0.3617 0.114 Uiso 1 1 calc R . . C10 C 0.3106(6) 0.8171(11) 0.3896(5) 0.095(3) Uani 1 1 d . . . C11 C 0.3231(6) 0.6946(12) 0.4579(5) 0.105(4) Uani 1 1 d . . . C12 C 0.3443(8) 0.6218(13) 0.5078(6) 0.138(6) Uani 1 1 d . . . H12A H 0.3828 0.6291 0.5424 0.166 Uiso 1 1 calc R . . C13 C 0.3046(10) 0.5416(13) 0.5014(8) 0.157(7) Uani 1 1 d . . . H13A H 0.3175 0.4918 0.5316 0.189 Uiso 1 1 calc R . . C14 C 0.2479(7) 0.5310(9) 0.4535(6) 0.124(4) Uani 1 1 d . . . H14A H 0.2217 0.4751 0.4518 0.149 Uiso 1 1 calc R . . C15 C 0.2273(7) 0.6037(10) 0.4054(4) 0.100(3) Uani 1 1 d . . . H15A H 0.1871 0.5960 0.3729 0.120 Uiso 1 1 calc R . . C16 C 0.2658(5) 0.6847(10) 0.4066(4) 0.082(3) Uani 1 1 d . . . O1 O 0.1954(4) 0.8084(6) 0.1753(3) 0.120(2) Uani 1 1 d . . . O2 O 0.3011(6) 0.7513(7) 0.1923(4) 0.184(5) Uani 1 1 d . . . C17 C 0.2488(7) 0.7756(7) 0.1535(5) 0.098(3) Uani 1 1 d . . . C18 C 0.2508(5) 0.7615(6) 0.0726(4) 0.070(2) Uani 1 1 d . . . C19 C 0.1890(5) 0.7750(7) 0.0295(5) 0.099(3) Uani 1 1 d . . . H19A H 0.1468 0.7936 0.0496 0.119 Uiso 1 1 calc R . . C20 C 0.3131(5) 0.7384(7) 0.0442(5) 0.098(3) Uani 1 1 d . . . H20A H 0.3563 0.7315 0.0726 0.118 Uiso 1 1 calc R . . N6 N 0.1177(5) 0.7063(9) 0.2780(5) 0.116(3) Uani 1 1 d . . . C21 C 0.0645(9) 0.6853(10) 0.2655(10) 0.163(7) Uani 1 1 d . . . N7 N 0.0000 0.646(2) 0.2500 0.269(14) Uani 1 2 d SU . . Cl1 Cl 0.4500(10) 0.9343(13) 0.1501(10) 0.135(3) Uani 0.197(5) 1 d PDU A 1 O3 O 0.478(2) 0.8424(16) 0.136(3) 0.245(17) Uani 0.197(5) 1 d PDU A 1 O4 O 0.429(2) 0.937(3) 0.2221(14) 0.192(11) Uani 0.197(5) 1 d PDU A 1 O5 O 0.3871(17) 0.954(3) 0.102(2) 0.34(3) Uani 0.197(5) 1 d PDU A 1 O6 O 0.5051(16) 1.003(2) 0.141(2) 0.157(15) Uani 0.197(5) 1 d PDU A 1 Cl1' Cl 0.4668(6) 0.8937(9) 0.1937(6) 0.135(3) Uani 0.303(5) 1 d PDU . 2 O3' O 0.4484(15) 0.835(2) 0.2518(13) 0.245(17) Uani 0.303(5) 1 d PDU . 2 O4' O 0.5316(9) 0.9464(18) 0.2153(16) 0.192(11) Uani 0.303(5) 1 d PDU . 2 O5' O 0.4796(17) 0.836(2) 0.1334(12) 0.34(3) Uani 0.303(5) 1 d PDU A 2 O6' O 0.4075(11) 0.9572(16) 0.1750(17) 0.194(15) Uani 0.303(5) 1 d PDU A 2 C22 C 0.5189(16) 0.850(2) 0.511(2) 0.230(19) Uani 0.50 1 d PD . . H22A H 0.5443 0.9037 0.4946 0.276 Uiso 0.50 1 calc PR . . H22B H 0.5073 0.8082 0.4715 0.276 Uiso 0.50 1 calc PR . . H22C H 0.5491 0.8179 0.5468 0.276 Uiso 0.50 1 calc PR . . O7 O 0.4525(10) 0.8799(17) 0.5397(12) 0.224(11) Uani 0.50 1 d PD . . H7 H 0.4616 0.9329 0.5707 0.269 Uiso 0.50 1 d PR . . 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 0.0853(7) 0.1031(8) 0.0437(5) -0.0050(5) 0.0071(4) 0.0226(7) N1 0.067(4) 0.154(8) 0.062(5) 0.002(5) 0.021(4) 0.029(5) N2 0.066(4) 0.092(6) 0.050(3) -0.006(3) 0.014(3) 0.007(4) N3 0.099(6) 0.063(5) 0.076(4) -0.003(4) 0.004(4) -0.002(5) N4 0.081(5) 0.095(6) 0.044(4) 0.002(4) 0.010(4) 0.034(5) N5 0.090(6) 0.185(11) 0.063(5) -0.030(6) -0.003(5) 0.025(7) C1 0.085(6) 0.146(10) 0.068(6) 0.008(6) 0.037(5) -0.007(7) C2 0.078(6) 0.098(8) 0.048(4) -0.006(5) 0.011(4) -0.018(6) C3 0.073(6) 0.073(7) 0.038(4) -0.014(4) 0.016(4) -0.011(5) C4 0.076(6) 0.097(7) 0.050(4) -0.012(4) 0.014(4) -0.008(6) C5 0.060(6) 0.159(12) 0.070(6) -0.018(7) 0.019(5) 0.001(7) C6 0.080(8) 0.145(12) 0.082(7) -0.028(7) 0.020(5) 0.026(8) C7 0.097(7) 0.107(9) 0.087(6) -0.024(6) 0.017(6) 0.020(7) C8 0.073(6) 0.090(8) 0.063(5) -0.013(5) 0.019(4) -0.012(6) C9 0.071(6) 0.127(10) 0.089(7) -0.010(7) 0.013(5) 0.013(6) C10 0.074(6) 0.159(11) 0.052(5) -0.019(7) 0.002(5) 0.039(8) C11 0.092(8) 0.167(12) 0.056(6) -0.012(8) 0.014(6) 0.039(9) C12 0.137(12) 0.233(17) 0.046(6) 0.007(10) 0.009(7) 0.100(12) C13 0.211(19) 0.205(19) 0.061(8) 0.019(11) 0.049(11) 0.090(14) C14 0.177(12) 0.141(11) 0.060(6) 0.004(7) 0.039(7) 0.058(9) C15 0.142(9) 0.118(9) 0.045(5) 0.004(6) 0.029(5) 0.064(9) C16 0.091(7) 0.111(9) 0.045(5) -0.017(7) 0.014(5) 0.033(7) O1 0.115(5) 0.191(7) 0.059(4) -0.034(4) 0.032(3) 0.019(5) O2 0.246(10) 0.235(10) 0.064(4) -0.041(5) -0.039(5) 0.167(9) C17 0.136(9) 0.092(8) 0.065(6) -0.022(5) -0.002(6) 0.041(7) C18 0.099(6) 0.076(6) 0.037(4) -0.001(4) 0.013(4) 0.031(5) C19 0.096(7) 0.137(9) 0.066(6) -0.028(5) 0.019(5) 0.040(6) C20 0.093(7) 0.130(8) 0.069(6) -0.027(6) -0.012(5) 0.045(6) N6 0.105(7) 0.137(9) 0.104(6) 0.009(6) 0.000(6) 0.023(8) C21 0.151(14) 0.088(11) 0.243(18) 0.009(11) -0.024(13) 0.080(13) N7 0.257(16) 0.244(16) 0.303(16) 0.000 -0.002(10) 0.000 Cl1 0.121(5) 0.135(6) 0.153(7) -0.036(5) 0.028(5) 0.008(5) O3 0.243(18) 0.247(18) 0.246(18) -0.001(7) 0.032(7) 0.001(7) O4 0.186(13) 0.197(13) 0.194(13) -0.010(7) 0.028(7) -0.002(7) O5 0.34(3) 0.34(3) 0.34(3) -0.002(7) 0.032(8) -0.004(7) O6 0.162(17) 0.150(17) 0.161(18) 0.002(10) 0.022(10) 0.002(10) Cl1' 0.121(5) 0.135(6) 0.153(7) -0.036(5) 0.028(5) 0.008(5) O3' 0.243(18) 0.247(18) 0.246(18) -0.001(7) 0.032(7) 0.001(7) O4' 0.186(13) 0.197(13) 0.194(13) -0.010(7) 0.028(7) -0.002(7) O5' 0.34(3) 0.34(3) 0.34(3) -0.002(7) 0.032(8) -0.004(7) O6' 0.186(17) 0.197(17) 0.199(17) -0.005(10) 0.014(10) 0.017(10) C22 0.23(4) 0.14(2) 0.34(5) 0.02(3) 0.15(4) 0.02(3) O7 0.159(17) 0.28(3) 0.22(2) -0.05(2) -0.119(16) 0.015(18) _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 O1 1.992(6) . ? Zn1 N4 2.031(7) . ? Zn1 N6 2.037(12) . ? Zn1 N2 2.047(7) . ? Zn1 N1 2.287(8) . ? N1 C1 1.427(12) . ? N1 C9 1.452(10) . ? N1 H1A 0.9100 . ? N2 C2 1.319(10) . ? N2 C3 1.389(9) . ? N3 C2 1.351(10) . ? N3 C8 1.360(9) . ? N3 H3A 0.8600 . ? N4 C10 1.299(12) . ? N4 C16 1.343(13) . ? N5 C11 1.321(13) . ? N5 C10 1.351(12) . ? N5 H5B 0.8600 . ? C1 C2 1.532(11) . ? C1 H1B 0.9700 . ? C1 H1C 0.9700 . ? C3 C8 1.353(11) . ? C3 C4 1.396(10) . ? C4 C5 1.376(12) . ? C4 H4A 0.9300 . ? C5 C6 1.356(13) . ? C5 H5A 0.9300 . ? C6 C7 1.324(13) . ? C6 H6A 0.9300 . ? C7 C8 1.405(12) . ? C7 H7A 0.9300 . ? C9 C10 1.484(14) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C16 1.383(13) . ? C11 C12 1.436(18) . ? C12 C13 1.357(18) . ? C12 H12A 0.9300 . ? C13 C14 1.336(18) . ? C13 H13A 0.9300 . ? C14 C15 1.410(14) . ? C14 H14A 0.9300 . ? C15 C16 1.354(13) . ? C15 H15A 0.9300 . ? O1 C17 1.191(10) . ? O2 C17 1.213(11) . ? C17 C18 1.545(11) . ? C18 C20 1.344(10) . ? C18 C19 1.358(11) . ? C19 C20 1.403(12) 7_565 ? C19 H19A 0.9300 . ? C20 C19 1.403(12) 7_565 ? C20 H20A 0.9300 . ? N6 C21 1.033(16) . ? C21 N7 1.33(2) . ? N7 C21 1.33(2) 2 ? Cl1 O6 1.435(5) . ? Cl1 O3 1.438(5) . ? Cl1 O5 1.439(5) . ? Cl1 O4 1.441(5) . ? Cl1' O5' 1.438(5) . ? Cl1' O3' 1.440(5) . ? Cl1' O4' 1.440(5) . ? Cl1' O6' 1.441(5) . ? Cl1' O4' 1.87(4) 2_655 ? Cl1' O3' 1.98(3) 2_655 ? Cl1' Cl1' 2.37(2) 2_655 ? O3' O4' 1.73(3) 2_655 ? O3' Cl1' 1.98(3) 2_655 ? O4' O3' 1.73(3) 2_655 ? O4' O4' 1.82(5) 2_655 ? O4' Cl1' 1.87(4) 2_655 ? C22 O7 1.441(5) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? O7 H7 0.9628 . ? 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 O1 Zn1 N4 137.7(3) . . ? O1 Zn1 N6 91.7(4) . . ? N4 Zn1 N6 97.8(4) . . ? O1 Zn1 N2 105.7(3) . . ? N4 Zn1 N2 111.6(2) . . ? N6 Zn1 N2 104.1(4) . . ? O1 Zn1 N1 90.9(3) . . ? N4 Zn1 N1 78.1(3) . . ? N6 Zn1 N1 175.8(4) . . ? N2 Zn1 N1 78.2(3) . . ? C1 N1 C9 113.9(8) . . ? C1 N1 Zn1 106.9(5) . . ? C9 N1 Zn1 107.1(6) . . ? C1 N1 H1A 109.6 . . ? C9 N1 H1A 109.6 . . ? Zn1 N1 H1A 109.6 . . ? C2 N2 C3 104.9(7) . . ? C2 N2 Zn1 114.4(6) . . ? C3 N2 Zn1 140.6(7) . . ? C2 N3 C8 106.8(7) . . ? C2 N3 H3A 126.6 . . ? C8 N3 H3A 126.6 . . ? C10 N4 C16 104.9(9) . . ? C10 N4 Zn1 116.0(7) . . ? C16 N4 Zn1 139.1(8) . . ? C11 N5 C10 108.7(11) . . ? C11 N5 H5B 125.6 . . ? C10 N5 H5B 125.6 . . ? N1 C1 C2 109.1(8) . . ? N1 C1 H1B 109.9 . . ? C2 C1 H1B 109.9 . . ? N1 C1 H1C 109.9 . . ? C2 C1 H1C 109.9 . . ? H1B C1 H1C 108.3 . . ? N2 C2 N3 111.8(7) . . ? N2 C2 C1 121.7(10) . . ? N3 C2 C1 126.4(10) . . ? C8 C3 N2 109.4(8) . . ? C8 C3 C4 120.2(8) . . ? N2 C3 C4 130.4(9) . . ? C5 C4 C3 116.3(9) . . ? C5 C4 H4A 121.9 . . ? C3 C4 H4A 121.9 . . ? C6 C5 C4 123.2(10) . . ? C6 C5 H5A 118.4 . . ? C4 C5 H5A 118.4 . . ? C7 C6 C5 120.4(10) . . ? C7 C6 H6A 119.8 . . ? C5 C6 H6A 119.8 . . ? C6 C7 C8 118.7(10) . . ? C6 C7 H7A 120.6 . . ? C8 C7 H7A 120.6 . . ? C3 C8 N3 107.0(8) . . ? C3 C8 C7 121.0(9) . . ? N3 C8 C7 132.0(10) . . ? N1 C9 C10 109.3(8) . . ? N1 C9 H9A 109.8 . . ? C10 C9 H9A 109.8 . . ? N1 C9 H9B 109.8 . . ? C10 C9 H9B 109.8 . . ? H9A C9 H9B 108.3 . . ? N4 C10 N5 111.2(13) . . ? N4 C10 C9 122.6(9) . . ? N5 C10 C9 126.0(12) . . ? N5 C11 C16 104.2(12) . . ? N5 C11 C12 133.1(13) . . ? C16 C11 C12 122.6(15) . . ? C13 C12 C11 115.7(15) . . ? C13 C12 H12A 122.2 . . ? C11 C12 H12A 122.2 . . ? C14 C13 C12 122.9(18) . . ? C14 C13 H13A 118.5 . . ? C12 C13 H13A 118.5 . . ? C13 C14 C15 120.6(15) . . ? C13 C14 H14A 119.7 . . ? C15 C14 H14A 119.7 . . ? C16 C15 C14 120.1(13) . . ? C16 C15 H15A 119.9 . . ? C14 C15 H15A 119.9 . . ? N4 C16 C15 131.1(10) . . ? N4 C16 C11 111.0(12) . . ? C15 C16 C11 118.0(13) . . ? C17 O1 Zn1 114.8(7) . . ? O1 C17 O2 122.7(9) . . ? O1 C17 C18 118.5(9) . . ? O2 C17 C18 118.8(10) . . ? C20 C18 C19 119.7(7) . . ? C20 C18 C17 120.9(8) . . ? C19 C18 C17 119.3(8) . . ? C18 C19 C20 122.1(8) . 7_565 ? C18 C19 H19A 119.0 . . ? C20 C19 H19A 119.0 7_565 . ? C18 C20 C19 118.2(8) . 7_565 ? C18 C20 H20A 120.9 . . ? C19 C20 H20A 120.9 7_565 . ? C21 N6 Zn1 149.1(15) . . ? N6 C21 N7 171.6(19) . . ? C21 N7 C21 129(3) 2 . ? O6 Cl1 O3 109.9(5) . . ? O6 Cl1 O5 109.5(5) . . ? O3 Cl1 O5 109.4(5) . . ? O6 Cl1 O4 109.5(5) . . ? O3 Cl1 O4 109.3(5) . . ? O5 Cl1 O4 109.3(5) . . ? O5' Cl1' O3' 109.6(5) . . ? O5' Cl1' O4' 109.7(5) . . ? O3' Cl1' O4' 109.1(5) . . ? O5' Cl1' O6' 109.3(5) . . ? O3' Cl1' O6' 109.4(5) . . ? O4' Cl1' O6' 109.7(5) . . ? O5' Cl1' O4' 164.5(13) . 2_655 ? O3' Cl1' O4' 61.4(15) . 2_655 ? O4' Cl1' O4' 65.2(16) . 2_655 ? O6' Cl1' O4' 86.0(13) . 2_655 ? O5' Cl1' O3' 90.0(13) . 2_655 ? O3' Cl1' O3' 65.4(18) . 2_655 ? O4' Cl1' O3' 58.2(14) . 2_655 ? O6' Cl1' O3' 160.3(12) . 2_655 ? O4' Cl1' O3' 74.8(9) 2_655 2_655 ? O5' Cl1' Cl1' 127.4(13) . 2_655 ? O3' Cl1' Cl1' 56.8(12) . 2_655 ? O4' Cl1' Cl1' 52.4(12) . 2_655 ? O6' Cl1' Cl1' 123.3(12) . 2_655 ? O4' Cl1' Cl1' 37.5(5) 2_655 2_655 ? O3' Cl1' Cl1' 37.4(4) 2_655 2_655 ? Cl1' O3' O4' 71.7(18) . 2_655 ? Cl1' O3' Cl1' 85.9(13) . 2_655 ? O4' O3' Cl1' 45.0(7) 2_655 2_655 ? Cl1' O4' O3' 76.8(17) . 2_655 ? Cl1' O4' O4' 69.0(11) . 2_655 ? O3' O4' O4' 82.6(15) 2_655 2_655 ? Cl1' O4' Cl1' 90.1(13) . 2_655 ? O3' O4' Cl1' 46.9(8) 2_655 2_655 ? O4' O4' Cl1' 45.8(11) 2_655 2_655 ? O7 C22 H22A 109.5 . . ? O7 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O7 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C22 O7 H7 110.5 . . ? 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 O1 Zn1 N1 C1 78.7(5) . . . . ? N4 Zn1 N1 C1 -142.6(5) . . . . ? N6 Zn1 N1 C1 -151(5) . . . . ? N2 Zn1 N1 C1 -27.2(5) . . . . ? O1 Zn1 N1 C9 -159.0(6) . . . . ? N4 Zn1 N1 C9 -20.2(5) . . . . ? N6 Zn1 N1 C9 -29(5) . . . . ? N2 Zn1 N1 C9 95.2(6) . . . . ? O1 Zn1 N2 C2 -71.1(6) . . . . ? N4 Zn1 N2 C2 88.6(6) . . . . ? N6 Zn1 N2 C2 -167.0(5) . . . . ? N1 Zn1 N2 C2 16.6(5) . . . . ? O1 Zn1 N2 C3 104.7(7) . . . . ? N4 Zn1 N2 C3 -95.6(8) . . . . ? N6 Zn1 N2 C3 8.8(8) . . . . ? N1 Zn1 N2 C3 -167.7(8) . . . . ? O1 Zn1 N4 C10 86.4(7) . . . . ? N6 Zn1 N4 C10 -172.3(6) . . . . ? N2 Zn1 N4 C10 -63.7(6) . . . . ? N1 Zn1 N4 C10 8.3(5) . . . . ? O1 Zn1 N4 C16 -90.2(9) . . . . ? N6 Zn1 N4 C16 11.1(8) . . . . ? N2 Zn1 N4 C16 119.7(7) . . . . ? N1 Zn1 N4 C16 -168.3(8) . . . . ? C9 N1 C1 C2 -86.9(9) . . . . ? Zn1 N1 C1 C2 31.1(8) . . . . ? C3 N2 C2 N3 1.1(8) . . . . ? Zn1 N2 C2 N3 178.3(5) . . . . ? C3 N2 C2 C1 179.0(7) . . . . ? Zn1 N2 C2 C1 -3.7(9) . . . . ? C8 N3 C2 N2 -2.3(9) . . . . ? C8 N3 C2 C1 179.9(7) . . . . ? N1 C1 C2 N2 -21.1(10) . . . . ? N1 C1 C2 N3 156.5(8) . . . . ? C2 N2 C3 C8 0.5(8) . . . . ? Zn1 N2 C3 C8 -175.5(6) . . . . ? C2 N2 C3 C4 179.3(7) . . . . ? Zn1 N2 C3 C4 3.3(12) . . . . ? C8 C3 C4 C5 -0.8(10) . . . . ? N2 C3 C4 C5 -179.5(7) . . . . ? C3 C4 C5 C6 1.5(13) . . . . ? C4 C5 C6 C7 -2.8(15) . . . . ? C5 C6 C7 C8 3.2(15) . . . . ? N2 C3 C8 N3 -1.9(8) . . . . ? C4 C3 C8 N3 179.2(6) . . . . ? N2 C3 C8 C7 -179.7(7) . . . . ? C4 C3 C8 C7 1.4(11) . . . . ? C2 N3 C8 C3 2.5(8) . . . . ? C2 N3 C8 C7 179.9(8) . . . . ? C6 C7 C8 C3 -2.6(13) . . . . ? C6 C7 C8 N3 -179.8(9) . . . . ? C1 N1 C9 C10 145.0(7) . . . . ? Zn1 N1 C9 C10 27.1(8) . . . . ? C16 N4 C10 N5 -1.4(9) . . . . ? Zn1 N4 C10 N5 -179.1(5) . . . . ? C16 N4 C10 C9 -176.4(7) . . . . ? Zn1 N4 C10 C9 5.9(10) . . . . ? C11 N5 C10 N4 0.6(11) . . . . ? C11 N5 C10 C9 175.4(9) . . . . ? N1 C9 C10 N4 -24.4(11) . . . . ? N1 C9 C10 N5 161.3(7) . . . . ? C10 N5 C11 C16 0.5(10) . . . . ? C10 N5 C11 C12 177.3(10) . . . . ? N5 C11 C12 C13 -176.0(12) . . . . ? C16 C11 C12 C13 0.4(17) . . . . ? C11 C12 C13 C14 -2(2) . . . . ? C12 C13 C14 C15 1.4(19) . . . . ? C13 C14 C15 C16 1.2(14) . . . . ? C10 N4 C16 C15 -179.0(9) . . . . ? Zn1 N4 C16 C15 -2.2(14) . . . . ? C10 N4 C16 C11 1.7(9) . . . . ? Zn1 N4 C16 C11 178.5(6) . . . . ? C14 C15 C16 N4 178.0(8) . . . . ? C14 C15 C16 C11 -2.7(12) . . . . ? N5 C11 C16 N4 -1.4(10) . . . . ? C12 C11 C16 N4 -178.6(8) . . . . ? N5 C11 C16 C15 179.3(8) . . . . ? C12 C11 C16 C15 2.0(13) . . . . ? N4 Zn1 O1 C17 -4.8(11) . . . . ? N6 Zn1 O1 C17 -108.3(9) . . . . ? N2 Zn1 O1 C17 146.5(8) . . . . ? N1 Zn1 O1 C17 68.5(8) . . . . ? Zn1 O1 C17 O2 -5.5(15) . . . . ? Zn1 O1 C17 C18 173.2(6) . . . . ? O1 C17 C18 C20 169.8(10) . . . . ? O2 C17 C18 C20 -11.5(16) . . . . ? O1 C17 C18 C19 -8.6(15) . . . . ? O2 C17 C18 C19 170.1(11) . . . . ? C20 C18 C19 C20 2.8(17) . . . 7_565 ? C17 C18 C19 C20 -178.8(9) . . . 7_565 ? C19 C18 C20 C19 -2.7(16) . . . 7_565 ? C17 C18 C20 C19 178.9(9) . . . 7_565 ? O1 Zn1 N6 C21 -70(3) . . . . ? N4 Zn1 N6 C21 151(3) . . . . ? N2 Zn1 N6 C21 37(3) . . . . ? N1 Zn1 N6 C21 160(4) . . . . ? Zn1 N6 C21 N7 162(12) . . . . ? N6 C21 N7 C21 -178(100) . . . 2 ? O5' Cl1' O3' O4' 166.2(16) . . . 2_655 ? O4' Cl1' O3' O4' 46.0(16) . . . 2_655 ? O6' Cl1' O3' O4' -74.0(16) . . . 2_655 ? O3' Cl1' O3' O4' 85.5(13) 2_655 . . 2_655 ? Cl1' Cl1' O3' O4' 43.7(8) 2_655 . . 2_655 ? O5' Cl1' O3' Cl1' 122.5(15) . . . 2_655 ? O4' Cl1' O3' Cl1' 2.3(15) . . . 2_655 ? O6' Cl1' O3' Cl1' -117.7(15) . . . 2_655 ? O4' Cl1' O3' Cl1' -43.7(8) 2_655 . . 2_655 ? O3' Cl1' O3' Cl1' 41.8(9) 2_655 . . 2_655 ? O5' Cl1' O4' O3' -77.2(19) . . . 2_655 ? O3' Cl1' O4' O3' 42.9(19) . . . 2_655 ? O6' Cl1' O4' O3' 162.7(18) . . . 2_655 ? O4' Cl1' O4' O3' 87.0(14) 2_655 . . 2_655 ? Cl1' Cl1' O4' O3' 45.3(8) 2_655 . . 2_655 ? O5' Cl1' O4' O4' -164.2(15) . . . 2_655 ? O3' Cl1' O4' O4' -44.1(14) . . . 2_655 ? O6' Cl1' O4' O4' 75.7(14) . . . 2_655 ? O3' Cl1' O4' O4' -87.0(14) 2_655 . . 2_655 ? Cl1' Cl1' O4' O4' -41.7(11) 2_655 . . 2_655 ? O5' Cl1' O4' Cl1' -122.5(16) . . . 2_655 ? O3' Cl1' O4' Cl1' -2.4(16) . . . 2_655 ? O6' Cl1' O4' Cl1' 117.4(16) . . . 2_655 ? O4' Cl1' O4' Cl1' 41.7(11) 2_655 . . 2_655 ? O3' Cl1' O4' Cl1' -45.3(8) 2_655 . . 2_655 ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.622 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.075 # Attachment 'complex_1_-_021014H.cif' data_021014h _database_code_depnum_ccdc_archive 'CCDC 761846' #TrackingRef 'complex_1_-_021014H.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 Cl Cu N8 O4' _chemical_formula_weight 506.37 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 7.736(2) _cell_length_b 14.158(4) _cell_length_c 19.267(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.564(6) _cell_angle_gamma 90.00 _cell_volume 2022.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 961 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1028 _exptl_absorpt_coefficient_mu 1.258 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6331 _exptl_absorpt_correction_T_max 0.7870 _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 8435 _diffrn_reflns_av_R_equivalents 0.1028 _diffrn_reflns_av_sigmaI/netI 0.1506 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3534 _reflns_number_gt 1806 _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^)+(0.0270P)^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 3534 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1600 _refine_ls_R_factor_gt 0.0637 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 0.19107(9) 0.02958(5) 0.24478(4) 0.0336(2) Uani 1 1 d . . . Cl1 Cl 0.6856(2) -0.03726(13) 0.36976(10) 0.0518(5) Uani 1 1 d . . . O1 O 0.5202(6) -0.0703(3) 0.3206(2) 0.0726(15) Uani 1 1 d . . . O2 O 0.8018(6) -0.1149(3) 0.3960(3) 0.0988(19) Uani 1 1 d . . . O3 O 0.6454(6) 0.0084(3) 0.4297(2) 0.0873(16) Uani 1 1 d . . . O4 O 0.7717(5) 0.0279(3) 0.3335(2) 0.0671(13) Uani 1 1 d . . . N1 N 0.1153(6) -0.0605(3) 0.3156(2) 0.0332(12) Uani 1 1 d . . . H1C H -0.0060 -0.0533 0.3064 0.040 Uiso 1 1 calc R . . N2 N 0.1582(6) -0.0874(3) 0.1871(3) 0.0339(12) Uani 1 1 d . . . N3 N 0.1489(6) -0.2434(3) 0.1843(3) 0.0429(14) Uani 1 1 d . . . H3A H 0.1450 -0.3008 0.1985 0.051 Uiso 1 1 calc R . . N4 N 0.2470(6) 0.1133(3) 0.3295(3) 0.0324(12) Uani 1 1 d . . . N5 N 0.2634(6) 0.1350(3) 0.4448(3) 0.0442(14) Uani 1 1 d . . . H5B H 0.2600 0.1225 0.4881 0.053 Uiso 1 1 calc R . . N6 N 0.3351(7) 0.0962(3) 0.1903(3) 0.0397(14) Uani 1 1 d . . . N7 N 0.5911(7) 0.1352(4) 0.1454(3) 0.0572(17) Uani 1 1 d . . . N8 N -0.0895(7) 0.0948(3) 0.1974(3) 0.0415(14) Uani 1 1 d . . . C1 C 0.1436(7) -0.1608(4) 0.2997(3) 0.0379(16) Uani 1 1 d . . . H1A H 0.2563 -0.1837 0.3319 0.045 Uiso 1 1 calc R . . H1B H 0.0460 -0.1994 0.3063 0.045 Uiso 1 1 calc R . . C2 C 0.1486(7) -0.1651(4) 0.2241(3) 0.0347(16) Uani 1 1 d . . . C3 C 0.1616(7) -0.1168(4) 0.1181(3) 0.0351(15) Uani 1 1 d . . . C4 C 0.1655(8) -0.0658(4) 0.0580(3) 0.0463(18) Uani 1 1 d . . . H4A H 0.1712 -0.0002 0.0591 0.056 Uiso 1 1 calc R . . C5 C 0.1609(9) -0.1150(5) -0.0034(4) 0.066(2) Uani 1 1 d . . . H5A H 0.1608 -0.0820 -0.0451 0.079 Uiso 1 1 calc R . . C6 C 0.1563(9) -0.2145(5) -0.0051(4) 0.071(2) Uani 1 1 d . . . H6A H 0.1542 -0.2460 -0.0477 0.082 Uiso 1 1 calc R . . C7 C 0.1548(8) -0.2651(5) 0.0547(4) 0.059(2) Uani 1 1 d . . . H7A H 0.1529 -0.3307 0.0539 0.069 Uiso 1 1 calc R . . C8 C 0.1563(8) -0.2154(4) 0.1169(4) 0.0424(17) Uani 1 1 d . . . C9 C 0.1946(7) -0.0294(4) 0.3917(3) 0.0381(15) Uani 1 1 d . . . H9A H 0.3043 -0.0643 0.4139 0.046 Uiso 1 1 calc R . . H9B H 0.1102 -0.0402 0.4197 0.046 Uiso 1 1 calc R . . C10 C 0.2349(7) 0.0740(4) 0.3896(3) 0.0346(16) Uani 1 1 d . . . C11 C 0.2922(7) 0.2077(4) 0.3473(3) 0.0361(16) Uani 1 1 d . . . C12 C 0.3225(7) 0.2818(4) 0.3057(3) 0.0434(17) Uani 1 1 d . . . H12A H 0.3168 0.2731 0.2573 0.052 Uiso 1 1 calc R . . C13 C 0.3615(8) 0.3688(4) 0.3380(4) 0.0527(19) Uani 1 1 d . . . H13A H 0.3846 0.4195 0.3113 0.063 Uiso 1 1 calc R . . C14 C 0.3671(9) 0.3822(5) 0.4104(4) 0.058(2) Uani 1 1 d . . . H14A H 0.3922 0.4420 0.4306 0.070 Uiso 1 1 calc R . . C15 C 0.3364(8) 0.3092(5) 0.4527(4) 0.060(2) Uani 1 1 d . . . H15A H 0.3402 0.3182 0.5009 0.072 Uiso 1 1 calc R . . C16 C 0.2994(8) 0.2215(4) 0.4195(4) 0.0409(17) Uani 1 1 d . . . C17 C 0.4602(10) 0.1116(4) 0.1726(3) 0.0328(16) Uani 1 1 d . . . C18 C -0.2411(9) 0.1099(4) 0.1762(3) 0.0343(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0326(5) 0.0347(4) 0.0322(5) 0.0028(4) -0.0019(3) 0.0023(4) Cl1 0.0377(11) 0.0691(12) 0.0480(12) 0.0121(11) 0.0036(10) 0.0043(11) O1 0.056(3) 0.100(4) 0.063(4) -0.007(3) 0.015(3) 0.006(3) O2 0.064(4) 0.087(4) 0.149(6) 0.062(4) 0.029(4) 0.005(3) O3 0.082(4) 0.117(5) 0.046(3) -0.013(3) -0.014(3) 0.020(3) O4 0.044(3) 0.072(3) 0.074(3) 0.023(3) -0.015(2) 0.011(3) N1 0.027(3) 0.040(3) 0.033(3) 0.003(2) 0.002(2) 0.002(2) N2 0.035(3) 0.032(3) 0.035(3) 0.004(3) 0.003(3) -0.001(2) N3 0.058(4) 0.029(3) 0.043(4) 0.002(3) 0.010(3) 0.005(3) N4 0.029(3) 0.035(3) 0.032(3) 0.000(3) 0.001(3) 0.000(2) N5 0.051(4) 0.056(4) 0.023(3) 0.002(3) -0.005(3) 0.002(3) N6 0.033(3) 0.044(3) 0.041(4) 0.007(2) -0.001(3) 0.006(3) N7 0.038(4) 0.076(4) 0.057(4) 0.036(3) 0.005(3) 0.007(3) N8 0.037(4) 0.046(3) 0.040(4) 0.007(3) 0.002(3) -0.003(3) C1 0.042(4) 0.038(4) 0.032(4) 0.006(3) 0.002(3) 0.006(3) C2 0.042(4) 0.029(4) 0.035(4) -0.002(3) 0.014(3) 0.006(3) C3 0.037(4) 0.040(4) 0.029(4) -0.005(3) 0.006(3) -0.002(3) C4 0.058(5) 0.044(4) 0.034(4) 0.000(3) -0.006(4) -0.002(3) C5 0.079(6) 0.077(6) 0.038(5) 0.002(4) -0.004(4) -0.007(5) C6 0.095(6) 0.067(5) 0.037(5) -0.013(4) -0.013(4) -0.019(5) C7 0.078(6) 0.044(4) 0.048(5) -0.005(4) -0.002(4) -0.005(4) C8 0.046(4) 0.040(4) 0.040(5) -0.002(4) 0.002(4) -0.001(3) C9 0.034(4) 0.047(4) 0.033(4) 0.010(4) 0.001(3) 0.004(4) C10 0.027(4) 0.043(4) 0.033(4) 0.005(3) 0.001(3) -0.001(3) C11 0.037(4) 0.039(4) 0.032(4) 0.000(3) 0.005(3) 0.000(3) C12 0.042(4) 0.043(4) 0.044(4) 0.001(4) -0.001(3) 0.001(3) C13 0.063(5) 0.040(5) 0.055(5) -0.002(4) 0.008(4) 0.001(4) C14 0.074(6) 0.036(4) 0.066(6) -0.010(4) 0.016(5) -0.001(4) C15 0.075(6) 0.060(5) 0.045(5) -0.013(4) 0.007(4) -0.001(4) C16 0.038(4) 0.035(4) 0.049(5) -0.001(4) 0.005(4) 0.003(3) C17 0.044(5) 0.025(4) 0.030(4) 0.007(3) 0.008(4) 0.002(4) C18 0.043(5) 0.031(4) 0.025(4) 0.003(3) -0.011(4) 0.006(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 Cu1 N4 1.963(5) . ? Cu1 N2 1.970(5) . ? Cu1 N6 1.975(5) . ? Cu1 N1 2.071(4) . ? Cu1 N8 2.295(5) . ? Cl1 O2 1.419(4) . ? Cl1 O4 1.431(4) . ? Cl1 O3 1.433(4) . ? Cl1 O1 1.436(4) . ? N1 C1 1.481(6) . ? N1 C9 1.486(6) . ? N1 H1C 0.9100 . ? N2 C2 1.325(6) . ? N2 C3 1.400(7) . ? N3 C2 1.348(6) . ? N3 C8 1.375(7) . ? N3 H3A 0.8600 . ? N4 C10 1.312(6) . ? N4 C11 1.401(6) . ? N5 C10 1.339(7) . ? N5 C16 1.376(6) . ? N5 H5B 0.8600 . ? N6 C17 1.135(7) . ? N7 C17 1.310(8) . ? N7 C18 1.315(8) 1_655 ? N8 C18 1.146(7) . ? C1 C2 1.470(7) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C3 C4 1.372(7) . ? C3 C8 1.396(7) . ? C4 C5 1.364(8) . ? C4 H4A 0.9300 . ? C5 C6 1.409(8) . ? C5 H5A 0.9300 . ? C6 C7 1.359(8) . ? C6 H6A 0.9300 . ? C7 C8 1.386(8) . ? C7 H7A 0.9300 . ? C9 C10 1.499(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C12 1.381(7) . ? C11 C16 1.388(7) . ? C12 C13 1.374(7) . ? C12 H12A 0.9300 . ? C13 C14 1.396(8) . ? C13 H13A 0.9300 . ? C14 C15 1.378(8) . ? C14 H14A 0.9300 . ? C15 C16 1.390(7) . ? C15 H15A 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 N4 Cu1 N2 159.9(2) . . ? N4 Cu1 N6 97.43(19) . . ? N2 Cu1 N6 95.9(2) . . ? N4 Cu1 N1 81.98(19) . . ? N2 Cu1 N1 80.73(18) . . ? N6 Cu1 N1 162.36(19) . . ? N4 Cu1 N8 92.72(18) . . ? N2 Cu1 N8 99.09(18) . . ? N6 Cu1 N8 102.09(19) . . ? N1 Cu1 N8 95.55(18) . . ? O2 Cl1 O4 109.7(3) . . ? O2 Cl1 O3 108.9(3) . . ? O4 Cl1 O3 109.9(3) . . ? O2 Cl1 O1 109.8(3) . . ? O4 Cl1 O1 109.9(3) . . ? O3 Cl1 O1 108.8(3) . . ? C1 N1 C9 116.4(4) . . ? C1 N1 Cu1 111.6(3) . . ? C9 N1 Cu1 110.6(3) . . ? C1 N1 H1C 105.8 . . ? C9 N1 H1C 105.8 . . ? Cu1 N1 H1C 105.8 . . ? C2 N2 C3 106.4(5) . . ? C2 N2 Cu1 114.4(4) . . ? C3 N2 Cu1 138.7(4) . . ? C2 N3 C8 107.9(5) . . ? C2 N3 H3A 126.0 . . ? C8 N3 H3A 126.0 . . ? C10 N4 C11 105.3(5) . . ? C10 N4 Cu1 115.1(4) . . ? C11 N4 Cu1 139.6(4) . . ? C10 N5 C16 107.2(5) . . ? C10 N5 H5B 126.4 . . ? C16 N5 H5B 126.4 . . ? C17 N6 Cu1 155.4(5) . . ? C17 N7 C18 121.7(5) . 1_655 ? C18 N8 Cu1 166.4(5) . . ? C2 C1 N1 107.0(4) . . ? C2 C1 H1A 110.3 . . ? N1 C1 H1A 110.3 . . ? C2 C1 H1B 110.3 . . ? N1 C1 H1B 110.3 . . ? H1A C1 H1B 108.6 . . ? N2 C2 N3 111.5(5) . . ? N2 C2 C1 121.3(5) . . ? N3 C2 C1 127.1(5) . . ? C4 C3 C8 121.3(6) . . ? C4 C3 N2 130.9(6) . . ? C8 C3 N2 107.8(5) . . ? C5 C4 C3 117.5(6) . . ? C5 C4 H4A 121.3 . . ? C3 C4 H4A 121.3 . . ? C4 C5 C6 121.6(6) . . ? C4 C5 H5A 119.2 . . ? C6 C5 H5A 119.2 . . ? C7 C6 C5 120.9(6) . . ? C7 C6 H6A 119.6 . . ? C5 C6 H6A 119.6 . . ? C6 C7 C8 117.7(6) . . ? C6 C7 H7A 121.1 . . ? C8 C7 H7A 121.1 . . ? N3 C8 C7 132.7(6) . . ? N3 C8 C3 106.3(5) . . ? C7 C8 C3 121.0(6) . . ? N1 C9 C10 107.1(5) . . ? N1 C9 H9A 110.3 . . ? C10 C9 H9A 110.3 . . ? N1 C9 H9B 110.3 . . ? C10 C9 H9B 110.3 . . ? H9A C9 H9B 108.6 . . ? N4 C10 N5 113.0(6) . . ? N4 C10 C9 120.3(6) . . ? N5 C10 C9 126.6(6) . . ? C12 C11 C16 120.7(6) . . ? C12 C11 N4 130.9(6) . . ? C16 C11 N4 108.4(5) . . ? C13 C12 C11 118.0(6) . . ? C13 C12 H12A 121.0 . . ? C11 C12 H12A 121.0 . . ? C12 C13 C14 120.9(6) . . ? C12 C13 H13A 119.5 . . ? C14 C13 H13A 119.5 . . ? C15 C14 C13 121.9(6) . . ? C15 C14 H14A 119.0 . . ? C13 C14 H14A 119.0 . . ? C14 C15 C16 116.4(6) . . ? C14 C15 H15A 121.8 . . ? C16 C15 H15A 121.8 . . ? N5 C16 C11 106.1(5) . . ? N5 C16 C15 131.9(6) . . ? C11 C16 C15 122.0(6) . . ? N6 C17 N7 172.7(7) . . ? N8 C18 N7 171.9(7) . 1_455 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.327 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.085 # Attachment 'complex_2_-_021114A.cif' data_021114a _database_code_depnum_ccdc_archive 'CCDC 761847' #TrackingRef 'complex_2_-_021114A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H31 Cl Mn N11 O7' _chemical_formula_weight 748.05 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' Mn Mn 0.3368 0.7283 '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 10.391(4) _cell_length_b 30.525(12) _cell_length_c 11.492(5) _cell_angle_alpha 90.00 _cell_angle_beta 107.061(8) _cell_angle_gamma 90.00 _cell_volume 3485(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 763 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 20.39 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1544 _exptl_absorpt_coefficient_mu 0.517 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.833691 _exptl_absorpt_correction_T_max 1.000000 _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 16684 _diffrn_reflns_av_R_equivalents 0.0759 _diffrn_reflns_av_sigmaI/netI 0.1039 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6130 _reflns_number_gt 3244 _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^)+(0.0560P)^2^+1.7412P] 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 6130 _refine_ls_number_parameters 491 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.1472 _refine_ls_R_factor_gt 0.0661 _refine_ls_wR_factor_ref 0.1506 _refine_ls_wR_factor_gt 0.1225 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.037 _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 Mn1 Mn 1.07009(7) 1.14768(2) 0.32316(6) 0.0413(2) Uani 1 1 d . . . N1 N 0.9628(4) 1.10760(13) 0.1500(3) 0.0478(11) Uani 1 1 d . . . N2 N 0.8504(4) 1.16144(12) 0.2845(4) 0.0455(10) Uani 1 1 d . . . N3 N 0.6551(4) 1.16850(14) 0.1414(4) 0.0562(12) Uani 1 1 d . . . H3A H 0.5954 1.1662 0.0717 0.067 Uiso 1 1 calc R . . N4 N 1.2321(4) 1.11565(12) 0.2634(3) 0.0404(10) Uani 1 1 d . . . N5 N 1.2971(4) 1.08137(14) 0.1212(4) 0.0557(12) Uani 1 1 d . . . H5A H 1.2915 1.0691 0.0525 0.067 Uiso 1 1 calc R . . N6 N 1.0928(5) 1.20369(16) 0.2056(5) 0.0783(16) Uani 1 1 d . . . N7 N 1.2128(6) 1.2509(2) 0.1051(7) 0.148(3) Uani 1 1 d . . . N8 N 1.1494(5) 1.31586(17) -0.0146(4) 0.0743(15) Uani 1 1 d . . . C1 C 0.8366(5) 1.12856(18) 0.0834(5) 0.0584(15) Uani 1 1 d . . . H1A H 0.7728 1.1066 0.0401 0.070 Uiso 1 1 calc R . . H1B H 0.8521 1.1490 0.0243 0.070 Uiso 1 1 calc R . . C2 C 0.7810(5) 1.15233(16) 0.1719(5) 0.0450(12) Uani 1 1 d . . . C3 C 0.6395(5) 1.18949(17) 0.2432(5) 0.0508(13) Uani 1 1 d . . . C4 C 0.5324(6) 1.2115(2) 0.2625(6) 0.0720(18) Uani 1 1 d . . . H4 H 0.4515 1.2148 0.2012 0.086 Uiso 1 1 calc R . . C5 C 0.5506(7) 1.2284(2) 0.3766(8) 0.080(2) Uani 1 1 d . . . H5 H 0.4795 1.2430 0.3936 0.096 Uiso 1 1 calc R . . C6 C 0.6724(7) 1.22442(19) 0.4678(6) 0.0753(18) Uani 1 1 d . . . H6 H 0.6819 1.2366 0.5440 0.090 Uiso 1 1 calc R . . C7 C 0.7798(6) 1.20243(17) 0.4463(5) 0.0592(15) Uani 1 1 d . . . H7 H 0.8610 1.1993 0.5072 0.071 Uiso 1 1 calc R . . C8 C 0.7626(5) 1.18524(16) 0.3313(5) 0.0486(13) Uani 1 1 d . . . C9 C 1.0519(5) 1.09958(19) 0.0759(5) 0.0617(16) Uani 1 1 d . . . H9A H 1.0406 1.1224 0.0151 0.074 Uiso 1 1 calc R . . H9B H 1.0296 1.0718 0.0341 0.074 Uiso 1 1 calc R . . C10 C 1.1939(5) 1.09883(16) 0.1544(5) 0.0457(13) Uani 1 1 d . . . C11 C 1.4130(5) 1.08651(15) 0.2163(5) 0.0457(13) Uani 1 1 d . . . C12 C 1.5453(6) 1.07365(17) 0.2340(5) 0.0550(14) Uani 1 1 d . . . H12 H 1.5714 1.0589 0.1739 0.066 Uiso 1 1 calc R . . C13 C 1.6348(6) 1.08356(17) 0.3428(6) 0.0593(15) Uani 1 1 d . . . H13 H 1.7246 1.0757 0.3574 0.071 Uiso 1 1 calc R . . C14 C 1.5952(5) 1.10542(17) 0.4338(5) 0.0558(14) Uani 1 1 d . . . H14 H 1.6594 1.1112 0.5077 0.067 Uiso 1 1 calc R . . C15 C 1.4644(5) 1.11861(15) 0.4175(5) 0.0468(13) Uani 1 1 d . . . H15 H 1.4389 1.1335 0.4778 0.056 Uiso 1 1 calc R . . C16 C 1.3718(5) 1.10837(15) 0.3052(4) 0.0407(12) Uani 1 1 d . . . C17 C 1.1414(6) 1.2266(2) 0.1559(6) 0.0700(18) Uani 1 1 d . . . C18 C 1.1736(5) 1.2860(2) 0.0419(6) 0.0688(18) Uani 1 1 d . . . C19 C 1.0220(7) 1.0704(2) 0.5121(6) 0.095(2) Uani 1 1 d . . . H19A H 0.9569 1.0916 0.5205 0.142 Uiso 1 1 calc R . . H19B H 1.0916 1.0677 0.5880 0.142 Uiso 1 1 calc R . . H19C H 0.9787 1.0426 0.4900 0.142 Uiso 1 1 calc R . . O1 O 1.0779(4) 1.08402(10) 0.4222(3) 0.0586(10) Uani 1 1 d . . . H1C H 1.1285 1.0625 0.3985 0.070 Uiso 1 1 calc R . . C31 C 0.3606(7) 0.1509(3) 0.8514(8) 0.132(3) Uani 1 1 d . . . H31A H 0.3220 0.1682 0.9023 0.199 Uiso 1 1 calc R . . H31B H 0.3108 0.1241 0.8304 0.199 Uiso 1 1 calc R . . H31C H 0.3569 0.1669 0.7786 0.199 Uiso 1 1 calc R . . O7 O 0.4904(4) 0.14161(18) 0.9120(4) 0.0984(15) Uani 1 1 d . . . H7A H 0.5251 0.1284 0.8667 0.148 Uiso 1 1 calc R . . Cl1 Cl 0.81765(16) 0.99308(5) 0.14646(14) 0.0685(5) Uani 1 1 d D . . O3 O 0.7708(15) 1.0016(5) 0.2517(9) 0.190(9) Uani 0.566(14) 1 d PD A 1 O4 O 0.9606(6) 1.0023(4) 0.1876(13) 0.172(7) Uani 0.566(14) 1 d PD A 1 O5 O 0.7474(12) 1.0188(4) 0.0525(9) 0.137(6) Uani 0.566(14) 1 d PD A 1 O6 O 0.8041(14) 0.9481(2) 0.1256(8) 0.113(6) Uani 0.566(14) 1 d PD A 1 O3' O 0.9185(17) 0.9614(6) 0.1655(16) 0.202(12) Uani 0.434(14) 1 d PD A 2 O4' O 0.8367(15) 1.0244(4) 0.2320(11) 0.120(7) Uani 0.434(14) 1 d PD A 2 O5' O 0.6904(13) 0.9711(6) 0.1259(18) 0.224(13) Uani 0.434(14) 1 d PD A 2 O6' O 0.812(2) 1.0131(5) 0.0282(9) 0.187(12) Uani 0.434(14) 1 d PD A 2 O2 O 0.2408(3) 1.01577(11) 0.3832(3) 0.0569(10) Uani 1 1 d . . . N9 N 0.1765(4) 0.92884(13) 0.2506(3) 0.0482(11) Uani 1 1 d . . . H9 H 0.1269 0.9555 0.2444 0.058 Uiso 1 1 d R . . N10 N 0.3544(4) 0.89148(15) 0.2325(4) 0.0524(11) Uani 1 1 d . . . N11 N 0.4383(4) 0.98688(12) 0.3795(3) 0.0408(10) Uani 1 1 d . . . C20 C 0.1376(5) 0.88579(15) 0.2401(4) 0.0438(12) Uani 1 1 d . . . C21 C 0.0166(6) 0.86538(18) 0.2357(5) 0.0572(14) Uani 1 1 d . . . H21 H -0.0568 0.8813 0.2434 0.069 Uiso 1 1 calc R . . C22 C 0.0102(6) 0.8208(2) 0.2194(5) 0.0691(17) Uani 1 1 d . . . H22 H -0.0694 0.8061 0.2157 0.083 Uiso 1 1 calc R . . C23 C 0.1198(8) 0.7973(2) 0.2085(6) 0.0800(19) Uani 1 1 d . . . H23 H 0.1119 0.7671 0.1970 0.096 Uiso 1 1 calc R . . C24 C 0.2401(7) 0.81717(19) 0.2141(5) 0.0700(17) Uani 1 1 d . . . H24 H 0.3133 0.8009 0.2075 0.084 Uiso 1 1 calc R . . C25 C 0.2491(6) 0.86246(17) 0.2299(4) 0.0499(13) Uani 1 1 d . . . C26 C 0.3053(5) 0.93007(17) 0.2451(4) 0.0449(13) Uani 1 1 d . . . C27 C 0.3809(5) 0.97228(17) 0.2529(4) 0.0527(14) Uani 1 1 d . . . H27A H 0.4529 0.9685 0.2158 0.063 Uiso 1 1 calc R . . H27B H 0.3206 0.9947 0.2075 0.063 Uiso 1 1 calc R . . C28 C 0.3609(5) 1.00814(14) 0.4345(5) 0.0422(12) Uani 1 1 d . . . C29 C 0.5799(5) 0.97668(15) 0.4364(4) 0.0448(12) Uani 1 1 d . . . H29A H 0.6317 0.9896 0.3873 0.054 Uiso 1 1 calc R . . H29B H 0.5909 0.9452 0.4344 0.054 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 Mn1 0.0518(5) 0.0344(4) 0.0350(4) -0.0030(4) 0.0085(4) 0.0012(4) N1 0.044(2) 0.061(3) 0.034(2) -0.008(2) 0.005(2) 0.007(2) N2 0.047(2) 0.040(2) 0.046(3) 0.002(2) 0.009(2) 0.003(2) N3 0.048(3) 0.058(3) 0.052(3) 0.012(2) -0.001(2) -0.001(2) N4 0.047(3) 0.042(2) 0.032(2) -0.0001(19) 0.011(2) 0.0020(19) N5 0.066(3) 0.059(3) 0.041(3) -0.013(2) 0.015(3) 0.002(2) N6 0.094(4) 0.051(3) 0.097(4) 0.031(3) 0.039(3) 0.006(3) N7 0.070(4) 0.139(6) 0.242(8) 0.146(6) 0.058(5) 0.035(4) N8 0.085(4) 0.067(4) 0.064(3) 0.036(3) 0.010(3) 0.004(3) C1 0.060(4) 0.067(4) 0.043(3) -0.004(3) 0.006(3) 0.000(3) C2 0.041(3) 0.043(3) 0.043(3) 0.007(3) -0.001(3) 0.000(3) C3 0.050(3) 0.041(3) 0.061(4) 0.014(3) 0.016(3) 0.005(3) C4 0.065(4) 0.066(4) 0.081(5) 0.018(4) 0.015(4) 0.014(3) C5 0.079(5) 0.056(4) 0.117(6) 0.018(4) 0.049(5) 0.021(4) C6 0.100(5) 0.055(4) 0.082(5) 0.002(3) 0.044(5) 0.013(4) C7 0.069(4) 0.048(3) 0.064(4) 0.004(3) 0.025(3) 0.002(3) C8 0.052(3) 0.039(3) 0.055(4) 0.006(3) 0.016(3) -0.002(3) C9 0.069(4) 0.072(4) 0.038(3) -0.013(3) 0.005(3) 0.001(3) C10 0.054(3) 0.043(3) 0.039(3) -0.004(2) 0.012(3) 0.001(3) C11 0.058(4) 0.038(3) 0.044(3) -0.001(2) 0.020(3) -0.005(3) C12 0.065(4) 0.048(3) 0.061(4) 0.001(3) 0.032(4) 0.000(3) C13 0.052(3) 0.053(4) 0.078(4) 0.014(3) 0.026(4) -0.005(3) C14 0.054(4) 0.057(4) 0.052(4) 0.013(3) 0.008(3) -0.009(3) C15 0.059(4) 0.038(3) 0.045(3) 0.000(2) 0.017(3) -0.009(3) C16 0.053(3) 0.032(3) 0.040(3) 0.003(2) 0.017(3) -0.005(2) C17 0.061(4) 0.058(4) 0.090(5) 0.034(4) 0.021(4) 0.018(3) C18 0.045(3) 0.071(4) 0.088(5) 0.032(4) 0.017(3) 0.007(3) C19 0.120(6) 0.099(5) 0.084(5) 0.023(4) 0.057(5) 0.015(4) O1 0.089(3) 0.045(2) 0.052(2) 0.0100(17) 0.037(2) 0.0164(18) C31 0.061(5) 0.166(8) 0.152(8) 0.000(7) 0.002(5) 0.008(5) O7 0.054(3) 0.151(5) 0.081(3) -0.038(3) 0.005(2) 0.014(3) Cl1 0.0775(11) 0.0559(10) 0.0667(11) -0.0144(8) 0.0127(9) 0.0088(9) O3 0.217(18) 0.26(2) 0.113(10) -0.021(12) 0.083(11) 0.094(16) O4 0.071(7) 0.089(9) 0.322(19) 0.014(10) 0.006(9) 0.011(6) O5 0.139(10) 0.154(12) 0.106(9) 0.075(8) 0.019(7) 0.073(9) O6 0.198(15) 0.043(5) 0.072(6) -0.016(4) -0.001(7) -0.005(7) O3' 0.19(2) 0.14(2) 0.28(2) -0.045(17) 0.077(19) 0.109(18) O4' 0.169(15) 0.107(10) 0.112(11) -0.091(9) 0.085(10) -0.054(9) O5' 0.130(14) 0.134(16) 0.43(4) -0.119(18) 0.106(17) -0.079(12) O6' 0.30(3) 0.137(17) 0.098(13) -0.013(11) 0.011(15) -0.084(17) O2 0.047(2) 0.045(2) 0.068(3) -0.0050(18) 0.001(2) 0.0055(17) N9 0.054(3) 0.035(3) 0.048(3) -0.004(2) 0.004(2) 0.010(2) N10 0.057(3) 0.052(3) 0.044(3) -0.006(2) 0.007(2) 0.009(2) N11 0.046(2) 0.036(2) 0.037(2) -0.0045(19) 0.006(2) -0.0015(19) C20 0.056(3) 0.033(3) 0.036(3) -0.002(2) 0.003(3) 0.003(3) C21 0.061(4) 0.053(4) 0.053(3) -0.008(3) 0.009(3) 0.000(3) C22 0.082(4) 0.057(4) 0.062(4) -0.004(3) 0.012(4) -0.017(4) C23 0.112(6) 0.041(4) 0.081(5) -0.014(3) 0.020(4) -0.010(4) C24 0.093(5) 0.052(4) 0.061(4) -0.007(3) 0.016(4) 0.017(4) C25 0.063(4) 0.049(4) 0.032(3) -0.003(2) 0.006(3) 0.008(3) C26 0.055(3) 0.046(3) 0.027(3) -0.008(2) 0.002(3) -0.003(3) C27 0.061(3) 0.054(3) 0.039(3) -0.002(3) 0.009(3) -0.002(3) C28 0.047(3) 0.026(3) 0.051(3) 0.004(2) 0.010(3) -0.001(2) C29 0.051(3) 0.035(3) 0.048(3) 0.000(2) 0.013(3) 0.002(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 Mn1 N8 2.120(5) 4_586 ? Mn1 N4 2.223(4) . ? Mn1 N2 2.234(4) . ? Mn1 N6 2.234(5) . ? Mn1 O1 2.241(3) . ? Mn1 N1 2.323(4) . ? N1 C9 1.451(6) . ? N1 C1 1.458(6) . ? N2 C2 1.313(6) . ? N2 C8 1.392(6) . ? N3 C2 1.345(6) . ? N3 C3 1.384(7) . ? N3 H3A 0.8600 . ? N4 C10 1.303(6) . ? N4 C16 1.407(6) . ? N5 C10 1.349(6) . ? N5 C11 1.377(6) . ? N5 H5A 0.8600 . ? N6 C17 1.114(7) . ? N7 C18 1.291(7) . ? N7 C17 1.302(8) . ? N8 C18 1.105(6) . ? N8 Mn1 2.120(5) 4_585 ? C1 C2 1.497(7) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C3 C4 1.373(7) . ? C3 C8 1.385(7) . ? C4 C5 1.370(9) . ? C4 H4 0.9300 . ? C5 C6 1.392(8) . ? C5 H5 0.9300 . ? C6 C7 1.385(7) . ? C6 H6 0.9300 . ? C7 C8 1.384(7) . ? C7 H7 0.9300 . ? C9 C10 1.487(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C12 1.386(7) . ? C11 C16 1.389(6) . ? C12 C13 1.356(7) . ? C12 H12 0.9300 . ? C13 C14 1.400(7) . ? C13 H13 0.9300 . ? C14 C15 1.376(7) . ? C14 H14 0.9300 . ? C15 C16 1.400(6) . ? C15 H15 0.9300 . ? C19 O1 1.389(6) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? O1 H1C 0.9300 . ? C31 O7 1.354(7) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? O7 H7A 0.8200 . ? Cl1 O4' 1.344(7) . ? Cl1 O5 1.362(6) . ? Cl1 O6 1.395(6) . ? Cl1 O3' 1.397(7) . ? Cl1 O5' 1.438(7) . ? Cl1 O4 1.448(6) . ? Cl1 O3 1.454(7) . ? Cl1 O6' 1.476(8) . ? O2 C28 1.236(5) . ? N9 C26 1.359(6) . ? N9 C20 1.370(6) . ? N9 H9 0.9555 . ? N10 C26 1.309(6) . ? N10 C25 1.401(6) . ? N11 C28 1.329(6) . ? N11 C29 1.457(6) . ? N11 C27 1.471(6) . ? C20 C21 1.391(7) . ? C20 C25 1.394(6) . ? C21 C22 1.373(7) . ? C21 H21 0.9300 . ? C22 C23 1.383(8) . ? C22 H22 0.9300 . ? C23 C24 1.374(8) . ? C23 H23 0.9300 . ? C24 C25 1.394(7) . ? C24 H24 0.9300 . ? C26 C27 1.498(7) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.503(6) 3_676 ? C29 C28 1.503(6) 3_676 ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? 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 N8 Mn1 N4 111.61(17) 4_586 . ? N8 Mn1 N2 100.80(17) 4_586 . ? N4 Mn1 N2 147.54(15) . . ? N8 Mn1 N6 92.7(2) 4_586 . ? N4 Mn1 N6 85.77(17) . . ? N2 Mn1 N6 91.07(16) . . ? N8 Mn1 O1 93.53(17) 4_586 . ? N4 Mn1 O1 81.82(13) . . ? N2 Mn1 O1 98.44(13) . . ? N6 Mn1 O1 167.45(16) . . ? N8 Mn1 N1 174.26(17) 4_586 . ? N4 Mn1 N1 73.77(14) . . ? N2 Mn1 N1 73.92(14) . . ? N6 Mn1 N1 89.67(18) . . ? O1 Mn1 N1 85.15(14) . . ? C9 N1 C1 113.4(4) . . ? C9 N1 Mn1 111.3(3) . . ? C1 N1 Mn1 110.5(3) . . ? C2 N2 C8 105.0(4) . . ? C2 N2 Mn1 113.0(3) . . ? C8 N2 Mn1 140.2(3) . . ? C2 N3 C3 107.2(4) . . ? C2 N3 H3A 126.4 . . ? C3 N3 H3A 126.4 . . ? C10 N4 C16 105.0(4) . . ? C10 N4 Mn1 115.2(3) . . ? C16 N4 Mn1 139.8(3) . . ? C10 N5 C11 108.2(4) . . ? C10 N5 H5A 125.9 . . ? C11 N5 H5A 125.9 . . ? C17 N6 Mn1 159.2(5) . . ? C18 N7 C17 126.7(6) . . ? C18 N8 Mn1 156.0(6) . 4_585 ? N1 C1 C2 108.8(4) . . ? N1 C1 H1A 109.9 . . ? C2 C1 H1A 109.9 . . ? N1 C1 H1B 109.9 . . ? C2 C1 H1B 109.9 . . ? H1A C1 H1B 108.3 . . ? N2 C2 N3 113.0(5) . . ? N2 C2 C1 124.2(4) . . ? N3 C2 C1 122.7(5) . . ? C4 C3 N3 131.6(6) . . ? C4 C3 C8 123.1(6) . . ? N3 C3 C8 105.3(5) . . ? C5 C4 C3 116.6(6) . . ? C5 C4 H4 121.7 . . ? C3 C4 H4 121.7 . . ? C4 C5 C6 121.8(6) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C7 C6 C5 120.7(6) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C8 C7 C6 118.0(6) . . ? C8 C7 H7 121.0 . . ? C6 C7 H7 121.0 . . ? C7 C8 C3 119.7(5) . . ? C7 C8 N2 130.6(5) . . ? C3 C8 N2 109.6(5) . . ? N1 C9 C10 109.7(4) . . ? N1 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? N1 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? N4 C10 N5 112.6(4) . . ? N4 C10 C9 123.1(5) . . ? N5 C10 C9 124.3(4) . . ? N5 C11 C12 133.1(5) . . ? N5 C11 C16 104.6(4) . . ? C12 C11 C16 122.3(5) . . ? C13 C12 C11 117.0(5) . . ? C13 C12 H12 121.5 . . ? C11 C12 H12 121.5 . . ? C12 C13 C14 121.5(5) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C15 C14 C13 122.2(5) . . ? C15 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? C14 C15 C16 116.3(5) . . ? C14 C15 H15 121.8 . . ? C16 C15 H15 121.8 . . ? C11 C16 C15 120.6(5) . . ? C11 C16 N4 109.5(4) . . ? C15 C16 N4 129.9(4) . . ? N6 C17 N7 172.6(7) . . ? N8 C18 N7 174.3(7) . . ? O1 C19 H19A 109.5 . . ? O1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C19 O1 Mn1 132.6(3) . . ? C19 O1 H1C 113.7 . . ? Mn1 O1 H1C 113.7 . . ? O7 C31 H31A 109.5 . . ? O7 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O7 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C31 O7 H7A 109.5 . . ? O4' Cl1 O5 95.6(10) . . ? O4' Cl1 O6 144.4(7) . . ? O5 Cl1 O6 115.4(6) . . ? O4' Cl1 O3' 115.9(8) . . ? O5 Cl1 O3' 136.7(9) . . ? O6 Cl1 O3' 51.5(7) . . ? O4' Cl1 O5' 112.5(7) . . ? O5 Cl1 O5' 83.4(10) . . ? O6 Cl1 O5' 58.1(6) . . ? O3' Cl1 O5' 108.3(7) . . ? O4' Cl1 O4 72.9(7) . . ? O5 Cl1 O4 114.0(6) . . ? O6 Cl1 O4 106.8(5) . . ? O3' Cl1 O4 55.4(8) . . ? O5' Cl1 O4 161.7(9) . . ? O4' Cl1 O3 43.8(6) . . ? O5 Cl1 O3 108.9(6) . . ? O6 Cl1 O3 106.1(6) . . ? O3' Cl1 O3 114.4(9) . . ? O5' Cl1 O3 72.8(9) . . ? O4 Cl1 O3 104.8(6) . . ? O4' Cl1 O6' 109.6(6) . . ? O5 Cl1 O6' 33.3(10) . . ? O6 Cl1 O6' 106.0(8) . . ? O3' Cl1 O6' 104.8(7) . . ? O5' Cl1 O6' 104.9(7) . . ? O4 Cl1 O6' 88.8(10) . . ? O3 Cl1 O6' 139.5(9) . . ? C26 N9 C20 106.9(4) . . ? C26 N9 H9 119.4 . . ? C20 N9 H9 132.3 . . ? C26 N10 C25 104.1(4) . . ? C28 N11 C29 124.3(4) . . ? C28 N11 C27 119.5(4) . . ? C29 N11 C27 116.2(4) . . ? N9 C20 C21 132.3(5) . . ? N9 C20 C25 105.5(5) . . ? C21 C20 C25 122.2(5) . . ? C22 C21 C20 117.2(5) . . ? C22 C21 H21 121.4 . . ? C20 C21 H21 121.4 . . ? C21 C22 C23 121.2(6) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C24 C23 C22 121.9(6) . . ? C24 C23 H23 119.1 . . ? C22 C23 H23 119.1 . . ? C23 C24 C25 118.1(6) . . ? C23 C24 H24 121.0 . . ? C25 C24 H24 121.0 . . ? C20 C25 C24 119.4(5) . . ? C20 C25 N10 109.8(4) . . ? C24 C25 N10 130.7(5) . . ? N10 C26 N9 113.7(4) . . ? N10 C26 C27 124.5(5) . . ? N9 C26 C27 121.8(5) . . ? N11 C27 C26 111.9(4) . . ? N11 C27 H27A 109.2 . . ? C26 C27 H27A 109.2 . . ? N11 C27 H27B 109.2 . . ? C26 C27 H27B 109.2 . . ? H27A C27 H27B 107.9 . . ? O2 C28 N11 122.2(5) . . ? O2 C28 C29 118.5(5) . 3_676 ? N11 C28 C29 119.4(4) . 3_676 ? N11 C29 C28 116.4(4) . 3_676 ? N11 C29 H29A 108.2 . . ? C28 C29 H29A 108.2 3_676 . ? N11 C29 H29B 108.2 . . ? C28 C29 H29B 108.2 3_676 . ? H29A C29 H29B 107.4 . . ? 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 N8 Mn1 N1 C9 178(33) 4_586 . . . ? N4 Mn1 N1 C9 -22.6(3) . . . . ? N2 Mn1 N1 C9 154.2(4) . . . . ? N6 Mn1 N1 C9 63.0(3) . . . . ? O1 Mn1 N1 C9 -105.5(3) . . . . ? N8 Mn1 N1 C1 50.6(19) 4_586 . . . ? N4 Mn1 N1 C1 -149.5(4) . . . . ? N2 Mn1 N1 C1 27.4(3) . . . . ? N6 Mn1 N1 C1 -63.8(3) . . . . ? O1 Mn1 N1 C1 127.6(3) . . . . ? N8 Mn1 N2 C2 162.9(3) 4_586 . . . ? N4 Mn1 N2 C2 -13.9(5) . . . . ? N6 Mn1 N2 C2 69.9(3) . . . . ? O1 Mn1 N2 C2 -101.9(3) . . . . ? N1 Mn1 N2 C2 -19.4(3) . . . . ? N8 Mn1 N2 C8 1.4(5) 4_586 . . . ? N4 Mn1 N2 C8 -175.4(4) . . . . ? N6 Mn1 N2 C8 -91.6(5) . . . . ? O1 Mn1 N2 C8 96.6(5) . . . . ? N1 Mn1 N2 C8 179.1(5) . . . . ? N8 Mn1 N4 C10 -169.0(3) 4_586 . . . ? N2 Mn1 N4 C10 7.6(5) . . . . ? N6 Mn1 N4 C10 -77.7(4) . . . . ? O1 Mn1 N4 C10 100.5(3) . . . . ? N1 Mn1 N4 C10 13.2(3) . . . . ? N8 Mn1 N4 C16 7.9(5) 4_586 . . . ? N2 Mn1 N4 C16 -175.5(4) . . . . ? N6 Mn1 N4 C16 99.1(5) . . . . ? O1 Mn1 N4 C16 -82.7(4) . . . . ? N1 Mn1 N4 C16 -170.0(5) . . . . ? N8 Mn1 N6 C17 83.4(16) 4_586 . . . ? N4 Mn1 N6 C17 -28.0(16) . . . . ? N2 Mn1 N6 C17 -175.7(16) . . . . ? O1 Mn1 N6 C17 -36(2) . . . . ? N1 Mn1 N6 C17 -101.8(16) . . . . ? C9 N1 C1 C2 -155.8(4) . . . . ? Mn1 N1 C1 C2 -30.1(5) . . . . ? C8 N2 C2 N3 0.3(5) . . . . ? Mn1 N2 C2 N3 -167.5(3) . . . . ? C8 N2 C2 C1 177.3(5) . . . . ? Mn1 N2 C2 C1 9.4(6) . . . . ? C3 N3 C2 N2 -1.0(6) . . . . ? C3 N3 C2 C1 -178.0(5) . . . . ? N1 C1 C2 N2 15.1(7) . . . . ? N1 C1 C2 N3 -168.3(4) . . . . ? C2 N3 C3 C4 179.8(5) . . . . ? C2 N3 C3 C8 1.2(5) . . . . ? N3 C3 C4 C5 179.4(6) . . . . ? C8 C3 C4 C5 -2.1(8) . . . . ? C3 C4 C5 C6 1.5(9) . . . . ? C4 C5 C6 C7 -0.9(9) . . . . ? C5 C6 C7 C8 0.9(8) . . . . ? C6 C7 C8 C3 -1.5(8) . . . . ? C6 C7 C8 N2 -179.0(5) . . . . ? C4 C3 C8 C7 2.2(8) . . . . ? N3 C3 C8 C7 -179.0(4) . . . . ? C4 C3 C8 N2 -179.8(5) . . . . ? N3 C3 C8 N2 -1.0(5) . . . . ? C2 N2 C8 C7 178.1(5) . . . . ? Mn1 N2 C8 C7 -19.5(8) . . . . ? C2 N2 C8 C3 0.4(5) . . . . ? Mn1 N2 C8 C3 162.8(4) . . . . ? C1 N1 C9 C10 153.2(4) . . . . ? Mn1 N1 C9 C10 27.9(5) . . . . ? C16 N4 C10 N5 -0.3(5) . . . . ? Mn1 N4 C10 N5 177.6(3) . . . . ? C16 N4 C10 C9 -179.6(5) . . . . ? Mn1 N4 C10 C9 -1.7(6) . . . . ? C11 N5 C10 N4 0.8(6) . . . . ? C11 N5 C10 C9 -179.9(5) . . . . ? N1 C9 C10 N4 -18.7(7) . . . . ? N1 C9 C10 N5 162.1(5) . . . . ? C10 N5 C11 C12 177.3(5) . . . . ? C10 N5 C11 C16 -0.9(5) . . . . ? N5 C11 C12 C13 -178.3(5) . . . . ? C16 C11 C12 C13 -0.4(7) . . . . ? C11 C12 C13 C14 0.6(7) . . . . ? C12 C13 C14 C15 -1.0(8) . . . . ? C13 C14 C15 C16 1.0(7) . . . . ? N5 C11 C16 C15 178.9(4) . . . . ? C12 C11 C16 C15 0.4(7) . . . . ? N5 C11 C16 N4 0.7(5) . . . . ? C12 C11 C16 N4 -177.7(4) . . . . ? C14 C15 C16 C11 -0.7(7) . . . . ? C14 C15 C16 N4 177.1(4) . . . . ? C10 N4 C16 C11 -0.2(5) . . . . ? Mn1 N4 C16 C11 -177.3(3) . . . . ? C10 N4 C16 C15 -178.2(5) . . . . ? Mn1 N4 C16 C15 4.7(8) . . . . ? Mn1 N6 C17 N7 -8(8) . . . . ? C18 N7 C17 N6 -169(6) . . . . ? Mn1 N8 C18 N7 88(8) 4_585 . . . ? C17 N7 C18 N8 -170(8) . . . . ? N8 Mn1 O1 C19 57.1(5) 4_586 . . . ? N4 Mn1 O1 C19 168.5(5) . . . . ? N2 Mn1 O1 C19 -44.3(5) . . . . ? N6 Mn1 O1 C19 176.8(8) . . . . ? N1 Mn1 O1 C19 -117.3(5) . . . . ? C26 N9 C20 C21 -177.6(5) . . . . ? C26 N9 C20 C25 0.7(5) . . . . ? N9 C20 C21 C22 177.3(5) . . . . ? C25 C20 C21 C22 -0.7(7) . . . . ? C20 C21 C22 C23 0.3(8) . . . . ? C21 C22 C23 C24 0.4(10) . . . . ? C22 C23 C24 C25 -0.8(9) . . . . ? N9 C20 C25 C24 -178.1(4) . . . . ? C21 C20 C25 C24 0.3(7) . . . . ? N9 C20 C25 N10 -0.8(5) . . . . ? C21 C20 C25 N10 177.6(4) . . . . ? C23 C24 C25 C20 0.4(8) . . . . ? C23 C24 C25 N10 -176.3(5) . . . . ? C26 N10 C25 C20 0.6(5) . . . . ? C26 N10 C25 C24 177.6(5) . . . . ? C25 N10 C26 N9 -0.2(5) . . . . ? C25 N10 C26 C27 179.9(4) . . . . ? C20 N9 C26 N10 -0.3(5) . . . . ? C20 N9 C26 C27 179.6(4) . . . . ? C28 N11 C27 C26 -81.8(6) . . . . ? C29 N11 C27 C26 98.3(5) . . . . ? N10 C26 C27 N11 -98.5(5) . . . . ? N9 C26 C27 N11 81.6(6) . . . . ? C29 N11 C28 O2 -179.3(4) . . . . ? C27 N11 C28 O2 0.8(7) . . . . ? C29 N11 C28 C29 0.3(7) . . . 3_676 ? C27 N11 C28 C29 -179.5(4) . . . 3_676 ? C28 N11 C29 C28 -0.3(7) . . . 3_676 ? C27 N11 C29 C28 179.5(4) . . . 3_676 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.432 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.059