# 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 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name A.Amoroso _publ_contact_author_email amorosoaj@cf.ac.uk _publ_section_title ; The Co-ordination Chemistry of bis(2,2'-bipyrid-6'-yl) ketone with first row transition metals: The reversible interconversion of a mononuclear complex and a dinuclear hemiketal containing species ; loop_ _publ_author_name A.Amoroso J.Knight P.Edwards # Attachment '- 1 Mn aja0608.cif' data_aja0608 _database_code_depnum_ccdc_archive 'CCDC 774563' #TrackingRef '- 1 Mn aja0608.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common aja0608 _chemical_melting_point ? _chemical_formula_moiety 'C21 H14 Cl2 Mn N4 O9' _chemical_formula_sum 'C21 H14 Cl2 Mn N4 O9' _chemical_formula_weight 592.20 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' 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 12.4434(4) _cell_length_b 12.9901(4) _cell_length_c 14.1014(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.5880(10) _cell_angle_gamma 90.00 _cell_volume 2205.88(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 16409 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.783 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1196 _exptl_absorpt_coefficient_mu 0.906 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8052 _exptl_absorpt_correction_T_max 0.9148 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16314 _diffrn_reflns_av_R_equivalents 0.0706 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.39 _reflns_number_total 4982 _reflns_number_gt 3639 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0538P)^2^+1.1078P] 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 4982 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0699 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1176 _refine_ls_wR_factor_gt 0.1066 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 C1 C 0.4898(2) -0.00739(19) 0.19454(19) 0.0188(6) Uani 1 1 d . . . C2 C 0.5411(2) -0.11040(19) 0.18251(18) 0.0184(6) Uani 1 1 d . . . C3 C 0.4723(2) -0.1838(2) 0.12755(19) 0.0217(6) Uani 1 1 d . . . H3 H 0.3969 -0.1684 0.0970 0.026 Uiso 1 1 calc R . . C4 C 0.5159(2) -0.2803(2) 0.11794(19) 0.0227(6) Uani 1 1 d . . . H4 H 0.4712 -0.3316 0.0788 0.027 Uiso 1 1 calc R . . C5 C 0.6252(2) -0.3012(2) 0.16600(19) 0.0219(6) Uani 1 1 d . . . H5 H 0.6564 -0.3669 0.1601 0.026 Uiso 1 1 calc R . . C6 C 0.6890(2) -0.22454(18) 0.22317(18) 0.0166(5) Uani 1 1 d . . . C7 C 0.8049(2) -0.24457(19) 0.27963(18) 0.0184(6) Uani 1 1 d . . . C8 C 0.8446(2) -0.3437(2) 0.3043(2) 0.0250(6) Uani 1 1 d . . . H8 H 0.7970 -0.4015 0.2865 0.030 Uiso 1 1 calc R . . C9 C 0.9542(3) -0.3568(2) 0.3549(2) 0.0292(7) Uani 1 1 d . . . H9 H 0.9828 -0.4239 0.3725 0.035 Uiso 1 1 calc R . . C10 C 1.0213(2) -0.2723(2) 0.3797(2) 0.0252(6) Uani 1 1 d . . . H10 H 1.0976 -0.2800 0.4122 0.030 Uiso 1 1 calc R . . C11 C 0.9761(2) -0.1760(2) 0.3565(2) 0.0228(6) Uani 1 1 d . . . H11 H 1.0223 -0.1175 0.3757 0.027 Uiso 1 1 calc R . . C12 C 0.5458(2) 0.09474(19) 0.18873(19) 0.0186(6) Uani 1 1 d . . . C13 C 0.4811(2) 0.1724(2) 0.13683(19) 0.0223(6) Uani 1 1 d . . . H13 H 0.4052 0.1605 0.1052 0.027 Uiso 1 1 calc R . . C14 C 0.5287(2) 0.2677(2) 0.13171(19) 0.0229(6) Uani 1 1 d . . . H14 H 0.4867 0.3217 0.0945 0.027 Uiso 1 1 calc R . . C15 C 0.6383(2) 0.2831(2) 0.18153(19) 0.0221(6) Uani 1 1 d . . . H15 H 0.6725 0.3481 0.1792 0.027 Uiso 1 1 calc R . . C16 C 0.6981(2) 0.20229(19) 0.23523(19) 0.0188(6) Uani 1 1 d . . . C17 C 0.8148(2) 0.21548(19) 0.29300(19) 0.0187(6) Uani 1 1 d . . . C18 C 0.8619(3) 0.3116(2) 0.3205(2) 0.0262(6) Uani 1 1 d . . . H18 H 0.8191 0.3724 0.3030 0.031 Uiso 1 1 calc R . . C19 C 0.9708(3) 0.3177(2) 0.3731(2) 0.0300(7) Uani 1 1 d . . . H19 H 1.0039 0.3830 0.3914 0.036 Uiso 1 1 calc R . . C20 C 1.0320(3) 0.2293(2) 0.3992(2) 0.0265(6) Uani 1 1 d . . . H20 H 1.1077 0.2321 0.4347 0.032 Uiso 1 1 calc R . . C21 C 0.9794(2) 0.1363(2) 0.3721(2) 0.0240(6) Uani 1 1 d . . . H21 H 1.0205 0.0747 0.3907 0.029 Uiso 1 1 calc R . . O1 O 0.39492(16) -0.00654(13) 0.20287(15) 0.0247(4) Uani 1 1 d . . . O2 O 0.82552(17) -0.00076(14) 0.14267(14) 0.0273(5) Uani 1 1 d . . . O3 O 0.7614(2) -0.12488(16) 0.02153(19) 0.0520(7) Uani 1 1 d . . . O4 O 0.8168(2) 0.0354(2) -0.02055(17) 0.0640(9) Uani 1 1 d . . . O5 O 0.65042(19) 0.01611(17) 0.02922(16) 0.0406(6) Uani 1 1 d . . . O6 O 0.79160(19) -0.03324(15) 0.44796(14) 0.0339(5) Uani 1 1 d . . . O7 O 0.62039(19) -0.00349(16) 0.4849(2) 0.0468(7) Uani 1 1 d . . . O8 O 0.7866(2) 0.00426(15) 0.60844(15) 0.0344(5) Uani 1 1 d . . . O9 O 0.74355(18) 0.13346(14) 0.48806(15) 0.0316(5) Uani 1 1 d . . . Cl1 Cl 0.76189(6) -0.01668(5) 0.04107(5) 0.02216(17) Uani 1 1 d . . . Cl2 Cl 0.73401(6) 0.02638(5) 0.50797(5) 0.02208(17) Uani 1 1 d . . . Mn1 Mn 0.78034(3) -0.01419(3) 0.28745(3) 0.01780(13) Uani 1 1 d . . . N1 N 0.64858(18) -0.12889(15) 0.22869(16) 0.0176(5) Uani 1 1 d . . . N2 N 0.86985(19) -0.16094(16) 0.30797(16) 0.0188(5) Uani 1 1 d . . . N3 N 0.65341(18) 0.10746(15) 0.23662(15) 0.0173(5) Uani 1 1 d . . . N4 N 0.87341(19) 0.12859(16) 0.32081(16) 0.0200(5) 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 C1 0.0162(14) 0.0234(13) 0.0154(13) 0.0008(10) 0.0013(11) 0.0013(11) C2 0.0195(15) 0.0197(13) 0.0171(13) 0.0023(10) 0.0068(12) -0.0001(11) C3 0.0189(16) 0.0272(14) 0.0195(14) 0.0037(11) 0.0061(12) -0.0018(11) C4 0.0246(17) 0.0242(14) 0.0191(14) -0.0013(11) 0.0049(12) -0.0060(12) C5 0.0283(17) 0.0164(13) 0.0229(14) -0.0003(10) 0.0100(13) -0.0024(11) C6 0.0180(15) 0.0165(12) 0.0170(13) 0.0004(10) 0.0076(11) -0.0027(10) C7 0.0221(15) 0.0192(13) 0.0157(13) 0.0004(10) 0.0081(11) 0.0013(11) C8 0.0270(18) 0.0198(14) 0.0289(16) 0.0007(11) 0.0085(13) 0.0007(11) C9 0.0290(18) 0.0244(15) 0.0346(17) 0.0047(12) 0.0087(14) 0.0096(13) C10 0.0180(16) 0.0320(16) 0.0251(15) 0.0037(12) 0.0045(12) 0.0059(12) C11 0.0209(16) 0.0242(14) 0.0231(14) -0.0013(11) 0.0055(12) -0.0010(11) C12 0.0204(15) 0.0190(13) 0.0179(13) -0.0023(10) 0.0076(12) 0.0008(11) C13 0.0206(16) 0.0270(14) 0.0178(13) -0.0026(11) 0.0022(12) 0.0017(11) C14 0.0277(17) 0.0208(13) 0.0192(14) 0.0017(11) 0.0040(12) 0.0050(12) C15 0.0295(17) 0.0178(13) 0.0216(14) 0.0017(10) 0.0110(12) 0.0012(11) C16 0.0233(16) 0.0186(13) 0.0175(13) -0.0003(10) 0.0109(12) 0.0000(11) C17 0.0205(15) 0.0192(13) 0.0189(13) -0.0017(10) 0.0095(11) -0.0012(11) C18 0.0292(18) 0.0196(14) 0.0301(16) 0.0000(11) 0.0081(14) -0.0040(12) C19 0.0328(19) 0.0243(15) 0.0331(17) -0.0062(12) 0.0090(14) -0.0121(13) C20 0.0213(16) 0.0320(16) 0.0265(15) -0.0059(12) 0.0065(13) -0.0090(12) C21 0.0209(16) 0.0235(14) 0.0280(16) -0.0035(11) 0.0068(12) -0.0013(12) O1 0.0174(11) 0.0284(10) 0.0285(11) 0.0007(8) 0.0061(9) 0.0001(8) O2 0.0248(11) 0.0402(12) 0.0166(10) -0.0013(8) 0.0046(9) -0.0042(9) O3 0.0446(16) 0.0320(12) 0.0649(17) -0.0174(11) -0.0133(13) 0.0117(11) O4 0.0630(19) 0.104(2) 0.0255(13) 0.0062(13) 0.0113(13) -0.0449(17) O5 0.0305(13) 0.0607(15) 0.0273(12) -0.0022(10) 0.0008(10) 0.0236(11) O6 0.0495(15) 0.0305(11) 0.0242(11) 0.0031(8) 0.0140(10) 0.0159(10) O7 0.0206(13) 0.0404(13) 0.0748(19) 0.0113(12) 0.0035(12) -0.0047(10) O8 0.0432(15) 0.0399(12) 0.0197(11) 0.0037(9) 0.0072(10) 0.0097(10) O9 0.0396(14) 0.0211(10) 0.0358(12) 0.0018(8) 0.0128(10) 0.0008(9) Cl1 0.0223(4) 0.0259(3) 0.0188(3) -0.0001(3) 0.0060(3) -0.0011(3) Cl2 0.0204(4) 0.0234(3) 0.0227(3) 0.0018(3) 0.0061(3) 0.0020(3) Mn1 0.0176(2) 0.0144(2) 0.0205(2) -0.00068(15) 0.00302(17) -0.00055(15) N1 0.0183(13) 0.0159(10) 0.0201(11) 0.0005(8) 0.0077(10) -0.0013(9) N2 0.0182(13) 0.0191(11) 0.0202(11) 0.0009(9) 0.0068(10) 0.0009(9) N3 0.0170(12) 0.0195(11) 0.0169(11) -0.0009(9) 0.0073(9) 0.0006(9) N4 0.0199(13) 0.0184(11) 0.0226(12) -0.0028(9) 0.0067(10) -0.0014(9) _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 C1 O1 1.216(3) . ? C1 C12 1.510(3) . ? C1 C2 1.510(3) . ? C2 N1 1.353(3) . ? C2 C3 1.381(4) . ? C3 C4 1.386(4) . ? C3 H3 0.9500 . ? C4 C5 1.386(4) . ? C4 H4 0.9500 . ? C5 C6 1.396(4) . ? C5 H5 0.9500 . ? C6 N1 1.350(3) . ? C6 C7 1.484(4) . ? C7 N2 1.353(3) . ? C7 C8 1.391(4) . ? C8 C9 1.381(4) . ? C8 H8 0.9500 . ? C9 C10 1.371(4) . ? C9 H9 0.9500 . ? C10 C11 1.377(4) . ? C10 H10 0.9500 . ? C11 N2 1.342(4) . ? C11 H11 0.9500 . ? C12 N3 1.349(3) . ? C12 C13 1.380(4) . ? C13 C14 1.382(4) . ? C13 H13 0.9500 . ? C14 C15 1.382(4) . ? C14 H14 0.9500 . ? C15 C16 1.395(4) . ? C15 H15 0.9500 . ? C16 N3 1.354(3) . ? C16 C17 1.485(4) . ? C17 N4 1.347(3) . ? C17 C18 1.392(4) . ? C18 C19 1.373(4) . ? C18 H18 0.9500 . ? C19 C20 1.376(4) . ? C19 H19 0.9500 . ? C20 C21 1.381(4) . ? C20 H20 0.9500 . ? C21 N4 1.339(4) . ? C21 H21 0.9500 . ? O2 Cl1 1.466(2) . ? O2 Mn1 2.2568(19) . ? O3 Cl1 1.432(2) . ? O4 Cl1 1.407(2) . ? O5 Cl1 1.420(2) . ? O6 Cl2 1.461(2) . ? O6 Mn1 2.246(2) . ? O7 Cl2 1.423(2) . ? O8 Cl2 1.432(2) . ? O9 Cl2 1.4299(19) . ? Mn1 N4 2.174(2) . ? Mn1 N2 2.190(2) . ? Mn1 N1 2.216(2) . ? Mn1 N3 2.222(2) . ? 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 C1 C12 118.0(2) . . ? O1 C1 C2 117.8(2) . . ? C12 C1 C2 123.9(2) . . ? N1 C2 C3 123.0(2) . . ? N1 C2 C1 119.8(2) . . ? C3 C2 C1 117.0(2) . . ? C2 C3 C4 118.5(3) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 119.3(3) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 119.3(2) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? N1 C6 C5 121.6(2) . . ? N1 C6 C7 117.2(2) . . ? C5 C6 C7 121.3(2) . . ? N2 C7 C8 121.4(3) . . ? N2 C7 C6 116.4(2) . . ? C8 C7 C6 122.1(2) . . ? C9 C8 C7 119.0(3) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C10 C9 C8 119.5(3) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 118.8(3) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? N2 C11 C10 123.0(3) . . ? N2 C11 H11 118.5 . . ? C10 C11 H11 118.5 . . ? N3 C12 C13 123.3(2) . . ? N3 C12 C1 119.6(2) . . ? C13 C12 C1 117.1(2) . . ? C12 C13 C14 118.8(3) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C13 C14 C15 119.0(3) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C14 C15 C16 119.4(2) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? N3 C16 C15 121.9(3) . . ? N3 C16 C17 116.4(2) . . ? C15 C16 C17 121.7(2) . . ? N4 C17 C18 120.7(3) . . ? N4 C17 C16 116.5(2) . . ? C18 C17 C16 122.8(2) . . ? C19 C18 C17 119.4(3) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C18 C19 C20 120.1(3) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C19 C20 C21 117.7(3) . . ? C19 C20 H20 121.2 . . ? C21 C20 H20 121.2 . . ? N4 C21 C20 123.2(3) . . ? N4 C21 H21 118.4 . . ? C20 C21 H21 118.4 . . ? Cl1 O2 Mn1 132.58(12) . . ? Cl2 O6 Mn1 127.59(12) . . ? O4 Cl1 O5 113.26(17) . . ? O4 Cl1 O3 109.41(17) . . ? O5 Cl1 O3 108.37(14) . . ? O4 Cl1 O2 108.00(13) . . ? O5 Cl1 O2 110.11(13) . . ? O3 Cl1 O2 107.54(13) . . ? O7 Cl2 O9 110.32(13) . . ? O7 Cl2 O8 110.59(15) . . ? O9 Cl2 O8 110.46(12) . . ? O7 Cl2 O6 109.10(14) . . ? O9 Cl2 O6 108.95(12) . . ? O8 Cl2 O6 107.34(12) . . ? N4 Mn1 N2 119.24(9) . . ? N4 Mn1 N1 163.34(8) . . ? N2 Mn1 N1 76.58(8) . . ? N4 Mn1 N3 76.10(8) . . ? N2 Mn1 N3 163.42(8) . . ? N1 Mn1 N3 87.63(8) . . ? N4 Mn1 O6 88.93(8) . . ? N2 Mn1 O6 82.55(7) . . ? N1 Mn1 O6 98.93(8) . . ? N3 Mn1 O6 105.21(7) . . ? N4 Mn1 O2 83.65(7) . . ? N2 Mn1 O2 87.28(7) . . ? N1 Mn1 O2 92.47(7) . . ? N3 Mn1 O2 88.40(7) . . ? O6 Mn1 O2 162.50(8) . . ? C6 N1 C2 118.2(2) . . ? C6 N1 Mn1 112.88(17) . . ? C2 N1 Mn1 127.52(16) . . ? C11 N2 C7 118.2(2) . . ? C11 N2 Mn1 126.69(17) . . ? C7 N2 Mn1 114.45(18) . . ? C12 N3 C16 117.6(2) . . ? C12 N3 Mn1 127.56(16) . . ? C16 N3 Mn1 113.01(17) . . ? C21 N4 C17 118.8(2) . . ? C21 N4 Mn1 125.38(17) . . ? C17 N4 Mn1 115.58(18) . . ? 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 C1 C2 N1 -140.2(3) . . . . ? C12 C1 C2 N1 45.0(4) . . . . ? O1 C1 C2 C3 36.7(3) . . . . ? C12 C1 C2 C3 -138.2(3) . . . . ? N1 C2 C3 C4 -1.1(4) . . . . ? C1 C2 C3 C4 -177.8(2) . . . . ? C2 C3 C4 C5 2.1(4) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? C4 C5 C6 N1 -3.5(4) . . . . ? C4 C5 C6 C7 177.2(2) . . . . ? N1 C6 C7 N2 -18.5(3) . . . . ? C5 C6 C7 N2 160.8(2) . . . . ? N1 C6 C7 C8 160.1(2) . . . . ? C5 C6 C7 C8 -20.6(4) . . . . ? N2 C7 C8 C9 -3.0(4) . . . . ? C6 C7 C8 C9 178.5(2) . . . . ? C7 C8 C9 C10 -0.1(4) . . . . ? C8 C9 C10 C11 2.5(4) . . . . ? C9 C10 C11 N2 -2.1(4) . . . . ? O1 C1 C12 N3 139.5(3) . . . . ? C2 C1 C12 N3 -45.6(4) . . . . ? O1 C1 C12 C13 -37.9(3) . . . . ? C2 C1 C12 C13 137.0(3) . . . . ? N3 C12 C13 C14 1.3(4) . . . . ? C1 C12 C13 C14 178.5(2) . . . . ? C12 C13 C14 C15 -2.3(4) . . . . ? C13 C14 C15 C16 0.3(4) . . . . ? C14 C15 C16 N3 2.9(4) . . . . ? C14 C15 C16 C17 -177.8(2) . . . . ? N3 C16 C17 N4 15.9(3) . . . . ? C15 C16 C17 N4 -163.4(2) . . . . ? N3 C16 C17 C18 -162.1(2) . . . . ? C15 C16 C17 C18 18.6(4) . . . . ? N4 C17 C18 C19 2.7(4) . . . . ? C16 C17 C18 C19 -179.3(3) . . . . ? C17 C18 C19 C20 -0.8(4) . . . . ? C18 C19 C20 C21 -1.0(4) . . . . ? C19 C20 C21 N4 1.1(4) . . . . ? Mn1 O2 Cl1 O4 159.84(18) . . . . ? Mn1 O2 Cl1 O5 35.71(19) . . . . ? Mn1 O2 Cl1 O3 -82.18(19) . . . . ? Mn1 O6 Cl2 O7 74.02(18) . . . . ? Mn1 O6 Cl2 O9 -46.5(2) . . . . ? Mn1 O6 Cl2 O8 -166.12(15) . . . . ? Cl2 O6 Mn1 N4 71.31(17) . . . . ? Cl2 O6 Mn1 N2 -169.01(18) . . . . ? Cl2 O6 Mn1 N1 -93.93(17) . . . . ? Cl2 O6 Mn1 N3 -3.96(19) . . . . ? Cl2 O6 Mn1 O2 136.0(2) . . . . ? Cl1 O2 Mn1 N4 -136.81(16) . . . . ? Cl1 O2 Mn1 N2 103.36(16) . . . . ? Cl1 O2 Mn1 N1 26.93(16) . . . . ? Cl1 O2 Mn1 N3 -60.63(16) . . . . ? Cl1 O2 Mn1 O6 157.74(19) . . . . ? C5 C6 N1 C2 4.5(3) . . . . ? C7 C6 N1 C2 -176.2(2) . . . . ? C5 C6 N1 Mn1 -163.20(19) . . . . ? C7 C6 N1 Mn1 16.1(3) . . . . ? C3 C2 N1 C6 -2.2(4) . . . . ? C1 C2 N1 C6 174.4(2) . . . . ? C3 C2 N1 Mn1 163.47(19) . . . . ? C1 C2 N1 Mn1 -19.9(3) . . . . ? N4 Mn1 N1 C6 154.8(2) . . . . ? N2 Mn1 N1 C6 -7.84(16) . . . . ? N3 Mn1 N1 C6 167.06(17) . . . . ? O6 Mn1 N1 C6 -87.91(17) . . . . ? O2 Mn1 N1 C6 78.77(17) . . . . ? N4 Mn1 N1 C2 -11.5(4) . . . . ? N2 Mn1 N1 C2 -174.1(2) . . . . ? N3 Mn1 N1 C2 0.8(2) . . . . ? O6 Mn1 N1 C2 105.8(2) . . . . ? O2 Mn1 N1 C2 -87.5(2) . . . . ? C10 C11 N2 C7 -0.9(4) . . . . ? C10 C11 N2 Mn1 169.2(2) . . . . ? C8 C7 N2 C11 3.4(4) . . . . ? C6 C7 N2 C11 -177.9(2) . . . . ? C8 C7 N2 Mn1 -167.8(2) . . . . ? C6 C7 N2 Mn1 10.8(3) . . . . ? N4 Mn1 N2 C11 13.3(2) . . . . ? N1 Mn1 N2 C11 -172.3(2) . . . . ? N3 Mn1 N2 C11 169.6(2) . . . . ? O6 Mn1 N2 C11 -71.2(2) . . . . ? O2 Mn1 N2 C11 94.5(2) . . . . ? N4 Mn1 N2 C7 -176.27(16) . . . . ? N1 Mn1 N2 C7 -1.91(17) . . . . ? N3 Mn1 N2 C7 -20.0(4) . . . . ? O6 Mn1 N2 C7 99.17(18) . . . . ? O2 Mn1 N2 C7 -95.10(17) . . . . ? C13 C12 N3 C16 1.8(4) . . . . ? C1 C12 N3 C16 -175.4(2) . . . . ? C13 C12 N3 Mn1 -161.64(19) . . . . ? C1 C12 N3 Mn1 21.1(3) . . . . ? C15 C16 N3 C12 -3.9(3) . . . . ? C17 C16 N3 C12 176.8(2) . . . . ? C15 C16 N3 Mn1 161.9(2) . . . . ? C17 C16 N3 Mn1 -17.4(3) . . . . ? N4 Mn1 N3 C12 175.0(2) . . . . ? N2 Mn1 N3 C12 16.2(4) . . . . ? N1 Mn1 N3 C12 -1.4(2) . . . . ? O6 Mn1 N3 C12 -100.0(2) . . . . ? O2 Mn1 N3 C12 91.1(2) . . . . ? N4 Mn1 N3 C16 10.87(16) . . . . ? N2 Mn1 N3 C16 -147.9(2) . . . . ? N1 Mn1 N3 C16 -165.52(17) . . . . ? O6 Mn1 N3 C16 95.87(17) . . . . ? O2 Mn1 N3 C16 -72.98(17) . . . . ? C20 C21 N4 C17 0.8(4) . . . . ? C20 C21 N4 Mn1 -173.8(2) . . . . ? C18 C17 N4 C21 -2.7(4) . . . . ? C16 C17 N4 C21 179.2(2) . . . . ? C18 C17 N4 Mn1 172.40(19) . . . . ? C16 C17 N4 Mn1 -5.7(3) . . . . ? N2 Mn1 N4 C21 -14.6(2) . . . . ? N1 Mn1 N4 C21 -175.1(2) . . . . ? N3 Mn1 N4 C21 172.2(2) . . . . ? O6 Mn1 N4 C21 66.3(2) . . . . ? O2 Mn1 N4 C21 -97.9(2) . . . . ? N2 Mn1 N4 C17 170.70(16) . . . . ? N1 Mn1 N4 C17 10.2(4) . . . . ? N3 Mn1 N4 C17 -2.50(17) . . . . ? O6 Mn1 N4 C17 -108.46(18) . . . . ? O2 Mn1 N4 C17 87.42(18) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.39 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.533 _refine_diff_density_min -0.529 _refine_diff_density_rms 0.096 # Attachment '2-Fe.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 774564' #TrackingRef '2-Fe.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common aja0505 _chemical_melting_point ? _chemical_formula_moiety 'C44 H34 Fe2 N8 O4, 2(Cl O4)' _chemical_formula_sum 'C44 H34 Cl2 Fe2 N8 O12' _chemical_formula_weight 1049.39 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pc21b _symmetry_space_group_name_Hall 'P -2bc -2c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, z+1/2' '-x, y+1/2, -z' 'x, y+1/2, -z+1/2' _cell_length_a 10.9746(2) _cell_length_b 15.6196(3) _cell_length_c 24.5741(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4212.46(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 94091 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour purple _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.655 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2144 _exptl_absorpt_coefficient_mu 0.894 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7880 _exptl_absorpt_correction_T_max 0.9160 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30798 _diffrn_reflns_av_R_equivalents 0.0749 _diffrn_reflns_av_sigmaI/netI 0.0661 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 26.37 _reflns_number_total 7923 _reflns_number_gt 6330 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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. Restraints were applied to the anisotropic displacement parameters of oxygenatoms O13 and O24 ; _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^)+(0.0732P)^2^+2.1655P] 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 0.267(19) _refine_ls_number_reflns 7923 _refine_ls_number_parameters 616 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1321 _refine_ls_wR_factor_gt 0.1211 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.039 _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 C1 C 0.1158(5) 0.8514(4) 0.7272(2) 0.0305(13) Uani 1 1 d . . . H1 H 0.1840 0.8884 0.7309 0.037 Uiso 1 1 calc R . . C2 C 0.1248(5) 0.7819(4) 0.6919(2) 0.0332(13) Uani 1 1 d . . . H2 H 0.1972 0.7712 0.6718 0.040 Uiso 1 1 calc R . . C3 C 0.0233(5) 0.7288(4) 0.6871(2) 0.0314(12) Uani 1 1 d . . . H3 H 0.0256 0.6811 0.6632 0.038 Uiso 1 1 calc R . . C4 C -0.0791(5) 0.7451(3) 0.7166(2) 0.0284(12) Uani 1 1 d . . . H4 H -0.1481 0.7088 0.7135 0.034 Uiso 1 1 calc R . . C5 C -0.0817(4) 0.8158(3) 0.7515(2) 0.0223(11) Uani 1 1 d . . . C6 C -0.1894(4) 0.8376(3) 0.78485(19) 0.0251(11) Uani 1 1 d . . . C7 C -0.2983(4) 0.7918(4) 0.7853(2) 0.0300(12) Uani 1 1 d . . . H7 H -0.3073 0.7415 0.7640 0.036 Uiso 1 1 calc R . . C8 C -0.3928(5) 0.8208(4) 0.8172(2) 0.0352(13) Uani 1 1 d . . . H8 H -0.4672 0.7898 0.8187 0.042 Uiso 1 1 calc R . . C9 C -0.3788(4) 0.8951(4) 0.8470(2) 0.0310(13) Uani 1 1 d . . . H9 H -0.4449 0.9171 0.8677 0.037 Uiso 1 1 calc R . . C10 C -0.2682(4) 0.9373(3) 0.84646(19) 0.0234(11) Uani 1 1 d . . . C11 C -0.2403(4) 1.0204(3) 0.8774(2) 0.0226(10) Uani 1 1 d . . . C12 C -0.3178(5) 1.1629(4) 0.8817(2) 0.0394(14) Uani 1 1 d . . . H12A H -0.2311 1.1771 0.8849 0.059 Uiso 1 1 calc R . . H12B H -0.3559 1.1649 0.9178 0.059 Uiso 1 1 calc R . . H12C H -0.3577 1.2043 0.8577 0.059 Uiso 1 1 calc R . . C13 C -0.2534(4) 1.0018(3) 0.93892(19) 0.0254(11) Uani 1 1 d . . . C14 C -0.3618(5) 0.9942(4) 0.9677(2) 0.0366(13) Uani 1 1 d . . . H14 H -0.4376 1.0018 0.9497 0.044 Uiso 1 1 calc R . . C15 C -0.3585(6) 0.9755(4) 1.0222(2) 0.0452(16) Uani 1 1 d . . . H15 H -0.4320 0.9706 1.0424 0.054 Uiso 1 1 calc R . . C16 C -0.2473(6) 0.9637(4) 1.0474(2) 0.0421(15) Uani 1 1 d . . . H16 H -0.2437 0.9500 1.0850 0.051 Uiso 1 1 calc R . . C17 C -0.1417(5) 0.9721(3) 1.0175(2) 0.0319(13) Uani 1 1 d . . . C18 C -0.0151(5) 0.9594(4) 1.0378(2) 0.0353(14) Uani 1 1 d . . . C19 C 0.0116(6) 0.9142(4) 1.0857(2) 0.0460(17) Uani 1 1 d . . . H19 H -0.0516 0.8936 1.1086 0.055 Uiso 1 1 calc R . . C20 C 0.1335(8) 0.9005(4) 1.0984(3) 0.061(2) Uani 1 1 d . . . H20 H 0.1551 0.8704 1.1306 0.073 Uiso 1 1 calc R . . C21 C 0.2231(6) 0.9309(5) 1.0639(3) 0.0507(18) Uani 1 1 d . . . H21 H 0.3068 0.9214 1.0719 0.061 Uiso 1 1 calc R . . C22 C 0.1897(5) 0.9749(4) 1.0180(2) 0.0402(14) Uani 1 1 d . . . H22 H 0.2520 0.9961 0.9948 0.048 Uiso 1 1 calc R . . C23 C -0.1316(5) 1.1857(4) 1.0068(2) 0.0337(13) Uani 1 1 d . . . H23 H -0.2030 1.1531 0.9998 0.040 Uiso 1 1 calc R . . C24 C -0.1375(5) 1.2519(4) 1.0445(2) 0.0361(14) Uani 1 1 d . . . H24 H -0.2125 1.2654 1.0619 0.043 Uiso 1 1 calc R . . C25 C -0.0343(6) 1.2975(4) 1.0565(2) 0.0394(15) Uani 1 1 d . . . H25 H -0.0358 1.3417 1.0831 0.047 Uiso 1 1 calc R . . C26 C 0.0723(6) 1.2778(4) 1.0290(2) 0.0343(13) Uani 1 1 d . . . H26 H 0.1452 1.3082 1.0368 0.041 Uiso 1 1 calc R . . C27 C 0.0718(5) 1.2123(3) 0.9893(2) 0.0274(11) Uani 1 1 d . . . C28 C 0.1790(4) 1.1921(3) 0.9564(2) 0.0239(11) Uani 1 1 d . . . C29 C 0.2862(5) 1.2376(4) 0.9562(2) 0.0327(12) Uani 1 1 d . . . H29 H 0.2959 1.2864 0.9788 0.039 Uiso 1 1 calc R . . C30 C 0.3800(5) 1.2112(4) 0.9223(2) 0.0368(14) Uani 1 1 d . . . H30 H 0.4541 1.2426 0.9214 0.044 Uiso 1 1 calc R . . C31 C 0.3664(5) 1.1401(4) 0.8901(2) 0.0336(13) Uani 1 1 d . . . H31 H 0.4313 1.1206 0.8676 0.040 Uiso 1 1 calc R . . C32 C 0.2555(4) 1.0972(3) 0.89103(19) 0.0269(12) Uani 1 1 d . . . C33 C 0.2244(4) 1.0189(3) 0.8562(2) 0.0240(11) Uani 1 1 d . . . C34 C 0.3044(5) 0.8770(4) 0.8434(3) 0.0478(17) Uani 1 1 d . . . H34A H 0.3330 0.8812 0.8057 0.072 Uiso 1 1 calc R . . H34B H 0.2183 0.8603 0.8436 0.072 Uiso 1 1 calc R . . H34C H 0.3526 0.8339 0.8628 0.072 Uiso 1 1 calc R . . C35 C 0.2332(4) 1.0439(4) 0.79485(19) 0.0279(11) Uani 1 1 d . . . C36 C 0.3398(5) 1.0639(4) 0.7675(2) 0.0364(14) Uani 1 1 d . . . H36 H 0.4164 1.0593 0.7852 0.044 Uiso 1 1 calc R . . C37 C 0.3325(5) 1.0904(4) 0.7142(2) 0.0407(15) Uani 1 1 d . . . H37 H 0.4048 1.1028 0.6944 0.049 Uiso 1 1 calc R . . C38 C 0.2203(5) 1.0991(4) 0.6892(2) 0.0340(14) Uani 1 1 d . . . H38 H 0.2145 1.1199 0.6530 0.041 Uiso 1 1 calc R . . C39 C 0.1161(4) 1.0768(3) 0.71816(18) 0.0235(11) Uani 1 1 d . . . C40 C -0.0104(5) 1.0801(4) 0.6978(2) 0.0274(12) Uani 1 1 d . . . C41 C -0.0435(5) 1.1196(4) 0.6493(2) 0.0343(13) Uani 1 1 d . . . H41 H 0.0169 1.1448 0.6267 0.041 Uiso 1 1 calc R . . C42 C -0.1646(5) 1.1220(4) 0.6341(2) 0.0411(15) Uani 1 1 d . . . H42 H -0.1889 1.1512 0.6020 0.049 Uiso 1 1 calc R . . C43 C -0.2501(5) 1.0810(4) 0.6665(2) 0.0361(13) Uani 1 1 d . . . H43 H -0.3338 1.0800 0.6566 0.043 Uiso 1 1 calc R . . C44 C -0.2101(4) 1.0417(4) 0.7135(2) 0.0324(12) Uani 1 1 d . . . H44 H -0.2686 1.0131 0.7355 0.039 Uiso 1 1 calc R . . Cl1 Cl 0.51918(12) 0.87312(11) 1.17882(6) 0.0395(4) Uani 1 1 d . . . Cl2 Cl 0.49890(14) 1.18886(12) 1.05995(6) 0.0455(4) Uani 1 1 d . . . Fe1 Fe -0.02201(6) 0.98606(5) 0.80646(3) 0.02080(16) Uani 1 1 d . . . Fe2 Fe 0.00703(6) 1.04757(5) 0.92824(3) 0.02118(16) Uani 1 1 d . . . N1 N 0.0145(3) 0.8687(3) 0.75665(17) 0.0249(9) Uani 1 1 d . . . N2 N -0.1750(3) 0.9080(3) 0.81589(16) 0.0225(9) Uani 1 1 d . . . N3 N -0.1454(3) 0.9925(3) 0.96458(15) 0.0241(9) Uani 1 1 d . . . N4 N 0.0730(4) 0.9896(3) 1.00428(16) 0.0300(9) Uani 1 1 d . . . N5 N -0.0286(4) 1.1660(3) 0.97972(17) 0.0267(10) Uani 1 1 d . . . N6 N 0.1643(4) 1.1231(3) 0.92275(15) 0.0232(9) Uani 1 1 d . . . N7 N 0.1259(3) 1.0496(3) 0.77028(15) 0.0238(9) Uani 1 1 d . . . N8 N -0.0941(3) 1.0414(3) 0.72985(15) 0.0254(9) Uani 1 1 d . . . O1 O 0.1098(2) 0.9882(2) 0.86747(12) 0.0226(7) Uani 1 1 d . . . O2 O -0.1230(3) 1.0478(2) 0.86673(12) 0.0228(7) Uani 1 1 d . . . O3 O -0.3305(3) 1.0783(2) 0.85935(15) 0.0308(9) Uani 1 1 d . . . O4 O 0.3181(3) 0.9591(2) 0.86988(15) 0.0301(8) Uani 1 1 d . . . O11 O 0.6378(5) 0.9002(4) 1.1604(2) 0.0838(18) Uani 1 1 d . . . O12 O 0.4727(4) 0.9353(3) 1.2166(2) 0.0631(14) Uani 1 1 d . . . O13 O 0.4417(7) 0.8636(5) 1.1354(3) 0.121(3) Uani 1 1 d U . . O14 O 0.5372(5) 0.7912(4) 1.2044(2) 0.0746(16) Uani 1 1 d . . . O21 O 0.5750(5) 1.1900(5) 1.0152(2) 0.093(2) Uani 1 1 d . . . O22 O 0.5695(5) 1.1786(4) 1.10797(19) 0.0761(16) Uani 1 1 d . . . O23 O 0.4292(10) 1.2620(6) 1.0634(3) 0.175(5) Uani 1 1 d . . . O24 O 0.4181(6) 1.1184(5) 1.0515(3) 0.108(2) Uani 1 1 d U . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.035(3) 0.029(3) 0.028(3) 0.001(2) 0.005(2) 0.001(2) C2 0.037(3) 0.035(3) 0.028(3) 0.002(3) 0.009(2) 0.013(3) C3 0.044(3) 0.018(3) 0.031(3) -0.004(2) 0.001(2) 0.008(2) C4 0.039(3) 0.022(3) 0.025(3) -0.002(2) -0.008(2) 0.000(2) C5 0.026(2) 0.022(3) 0.018(2) 0.001(2) -0.002(2) 0.002(2) C6 0.030(3) 0.024(3) 0.021(2) 0.005(2) -0.004(2) 0.001(2) C7 0.031(3) 0.030(3) 0.029(3) 0.001(2) -0.003(2) -0.005(2) C8 0.024(3) 0.041(4) 0.041(3) 0.000(3) 0.002(2) -0.001(3) C9 0.022(2) 0.041(4) 0.030(3) 0.002(3) 0.004(2) -0.003(2) C10 0.025(2) 0.025(3) 0.020(3) 0.005(2) 0.004(2) 0.003(2) C11 0.020(2) 0.023(3) 0.025(2) 0.002(2) 0.009(2) 0.005(2) C12 0.034(3) 0.027(3) 0.057(4) 0.000(3) 0.013(3) 0.007(2) C13 0.029(2) 0.020(3) 0.027(3) -0.003(2) 0.010(2) 0.000(2) C14 0.037(3) 0.033(3) 0.040(3) 0.000(3) 0.016(2) 0.000(3) C15 0.053(4) 0.038(4) 0.045(4) -0.002(3) 0.025(3) -0.006(3) C16 0.067(4) 0.033(4) 0.027(3) 0.000(2) 0.015(3) -0.010(3) C17 0.057(3) 0.018(3) 0.020(3) 0.000(2) 0.005(2) 0.000(3) C18 0.059(4) 0.021(3) 0.025(3) 0.001(2) 0.001(3) -0.005(3) C19 0.085(5) 0.035(4) 0.017(3) 0.007(3) -0.008(3) -0.011(3) C20 0.110(6) 0.046(4) 0.027(3) 0.012(3) -0.025(4) -0.004(4) C21 0.062(4) 0.050(5) 0.041(4) 0.006(3) -0.021(3) -0.004(4) C22 0.049(3) 0.037(4) 0.035(3) 0.007(3) -0.007(2) 0.004(3) C23 0.039(3) 0.030(3) 0.032(3) 0.003(3) 0.009(2) 0.005(3) C24 0.048(3) 0.029(3) 0.032(3) -0.005(3) 0.006(3) 0.011(3) C25 0.066(4) 0.027(3) 0.025(3) -0.004(2) 0.008(3) 0.002(3) C26 0.051(3) 0.024(3) 0.029(3) -0.001(3) -0.006(3) -0.005(3) C27 0.041(3) 0.019(3) 0.022(3) 0.008(2) -0.002(2) 0.001(2) C28 0.029(3) 0.019(3) 0.024(3) 0.005(2) -0.007(2) 0.000(2) C29 0.034(3) 0.027(3) 0.037(3) -0.001(3) -0.004(2) 0.002(2) C30 0.028(3) 0.046(4) 0.036(3) 0.000(3) -0.006(2) -0.008(3) C31 0.022(3) 0.042(4) 0.037(3) -0.007(3) -0.003(2) 0.000(2) C32 0.027(3) 0.034(3) 0.019(3) 0.005(2) -0.002(2) 0.005(2) C33 0.020(2) 0.026(3) 0.026(2) 0.002(2) 0.0056(19) 0.003(2) C34 0.036(3) 0.051(5) 0.056(4) 0.004(3) 0.006(3) 0.005(3) C35 0.027(2) 0.032(3) 0.025(2) 0.004(2) 0.006(2) 0.001(3) C36 0.030(3) 0.045(4) 0.034(3) -0.001(3) 0.007(2) -0.003(3) C37 0.030(3) 0.058(4) 0.034(3) 0.010(3) 0.016(2) -0.011(3) C38 0.043(3) 0.033(4) 0.026(3) 0.009(2) 0.011(2) -0.003(3) C39 0.034(3) 0.022(3) 0.015(2) 0.000(2) 0.009(2) -0.004(2) C40 0.037(3) 0.026(3) 0.019(3) -0.002(2) 0.002(2) 0.005(2) C41 0.048(3) 0.030(3) 0.025(3) 0.005(2) 0.006(2) 0.001(3) C42 0.047(3) 0.045(4) 0.032(3) 0.008(3) -0.004(3) 0.005(3) C43 0.038(3) 0.036(3) 0.034(3) 0.003(3) -0.004(3) 0.007(3) C44 0.028(2) 0.039(3) 0.030(3) -0.001(3) 0.000(2) 0.000(3) Cl1 0.0384(7) 0.0423(9) 0.0377(8) -0.0009(7) -0.0072(6) 0.0022(7) Cl2 0.0501(9) 0.0556(11) 0.0308(8) -0.0029(7) -0.0009(6) 0.0135(8) Fe1 0.0225(3) 0.0216(4) 0.0182(3) 0.0000(3) 0.0062(3) -0.0014(4) Fe2 0.0248(3) 0.0205(4) 0.0182(3) 0.0009(3) 0.0025(3) 0.0003(3) N1 0.031(2) 0.024(2) 0.020(2) -0.0028(18) 0.0041(17) 0.001(2) N2 0.021(2) 0.024(2) 0.022(2) 0.0034(18) -0.0008(17) 0.0011(17) N3 0.033(2) 0.020(2) 0.019(2) 0.0000(19) 0.0083(16) 0.000(2) N4 0.045(2) 0.021(2) 0.024(2) 0.001(2) -0.0055(19) 0.004(2) N5 0.035(2) 0.021(2) 0.024(2) -0.0002(18) 0.0010(19) -0.0003(19) N6 0.027(2) 0.022(2) 0.020(2) 0.0033(18) -0.0019(17) 0.0027(18) N7 0.030(2) 0.021(2) 0.021(2) 0.0011(19) 0.0059(16) 0.000(2) N8 0.028(2) 0.029(2) 0.020(2) 0.001(2) 0.0025(16) -0.002(2) O1 0.0193(14) 0.030(2) 0.0183(16) 0.0006(16) 0.0009(12) -0.0019(16) O2 0.0205(15) 0.0233(19) 0.0245(17) 0.0020(16) 0.0057(13) -0.0012(16) O3 0.0234(18) 0.026(2) 0.043(2) 0.0014(17) 0.0047(16) 0.0045(15) O4 0.0243(17) 0.030(2) 0.036(2) 0.0010(17) 0.0022(15) 0.0076(15) O11 0.076(3) 0.076(4) 0.099(4) 0.001(3) 0.053(3) -0.015(3) O12 0.064(3) 0.051(3) 0.074(4) -0.009(3) 0.026(3) -0.001(2) O13 0.121(5) 0.105(5) 0.137(5) -0.034(4) -0.087(4) 0.034(4) O14 0.099(4) 0.062(4) 0.062(3) 0.021(3) 0.028(3) 0.032(3) O21 0.054(3) 0.180(7) 0.046(3) 0.016(4) 0.013(2) -0.003(4) O22 0.088(4) 0.098(4) 0.042(3) 0.001(3) -0.025(3) 0.028(3) O23 0.280(10) 0.166(8) 0.079(4) -0.071(5) -0.096(6) 0.162(8) O24 0.086(4) 0.128(5) 0.109(4) 0.039(4) -0.017(3) -0.035(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 C1 N1 1.353(6) . ? C1 C2 1.394(7) . ? C1 H1 0.9500 . ? C2 C3 1.393(8) . ? C2 H2 0.9500 . ? C3 C4 1.361(7) . ? C3 H3 0.9500 . ? C4 C5 1.398(7) . ? C4 H4 0.9500 . ? C5 N1 1.346(6) . ? C5 C6 1.477(7) . ? C6 N2 1.348(6) . ? C6 C7 1.392(7) . ? C7 C8 1.376(7) . ? C7 H7 0.9500 . ? C8 C9 1.382(8) . ? C8 H8 0.9500 . ? C9 C10 1.381(7) . ? C9 H9 0.9500 . ? C10 N2 1.348(6) . ? C10 C11 1.535(7) . ? C11 O2 1.381(5) . ? C11 O3 1.412(6) . ? C11 C13 1.547(7) . ? C12 O3 1.437(7) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 N3 1.350(6) . ? C13 C14 1.389(7) . ? C14 C15 1.371(8) . ? C14 H14 0.9500 . ? C15 C16 1.380(9) . ? C15 H15 0.9500 . ? C16 C17 1.378(8) . ? C16 H16 0.9500 . ? C17 N3 1.340(6) . ? C17 C18 1.490(8) . ? C18 N4 1.355(7) . ? C18 C19 1.402(8) . ? C19 C20 1.391(9) . ? C19 H19 0.9500 . ? C20 C21 1.383(10) . ? C20 H20 0.9500 . ? C21 C22 1.371(8) . ? C21 H21 0.9500 . ? C22 N4 1.344(7) . ? C22 H22 0.9500 . ? C23 N5 1.347(6) . ? C23 C24 1.391(8) . ? C23 H23 0.9500 . ? C24 C25 1.370(8) . ? C24 H24 0.9500 . ? C25 C26 1.385(8) . ? C25 H25 0.9500 . ? C26 C27 1.415(7) . ? C26 H26 0.9500 . ? C27 N5 1.339(7) . ? C27 C28 1.462(7) . ? C28 N6 1.370(6) . ? C28 C29 1.374(7) . ? C29 C30 1.387(8) . ? C29 H29 0.9500 . ? C30 C31 1.373(8) . ? C30 H30 0.9500 . ? C31 C32 1.390(7) . ? C31 H31 0.9500 . ? C32 N6 1.332(6) . ? C32 C33 1.531(7) . ? C33 O1 1.374(5) . ? C33 O4 1.430(6) . ? C33 C35 1.560(7) . ? C34 O4 1.446(7) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 N7 1.326(6) . ? C35 C36 1.384(7) . ? C36 C37 1.377(7) . ? C36 H36 0.9500 . ? C37 C38 1.381(8) . ? C37 H37 0.9500 . ? C38 C39 1.391(7) . ? C38 H38 0.9500 . ? C39 N7 1.354(6) . ? C39 C40 1.477(7) . ? C40 N8 1.353(7) . ? C40 C41 1.390(7) . ? C41 C42 1.381(8) . ? C41 H41 0.9500 . ? C42 C43 1.387(8) . ? C42 H42 0.9500 . ? C43 C44 1.380(7) . ? C43 H43 0.9500 . ? C44 N8 1.335(6) . ? C44 H44 0.9500 . ? Cl1 O13 1.372(6) . ? Cl1 O12 1.437(5) . ? Cl1 O14 1.439(5) . ? Cl1 O11 1.442(5) . ? Cl2 O23 1.377(7) . ? Cl2 O21 1.381(5) . ? Cl2 O22 1.421(5) . ? Cl2 O24 1.428(7) . ? Fe1 O1 2.084(3) . ? Fe1 O2 2.086(3) . ? Fe1 N2 2.088(4) . ? Fe1 N7 2.100(4) . ? Fe1 N8 2.218(4) . ? Fe1 N1 2.241(4) . ? Fe2 O2 2.079(3) . ? Fe2 N3 2.082(4) . ? Fe2 O1 2.089(3) . ? Fe2 N6 2.094(4) . ? Fe2 N4 2.199(4) . ? Fe2 N5 2.275(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 N1 C1 C2 123.1(5) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C3 C2 C1 117.3(5) . . ? C3 C2 H2 121.4 . . ? C1 C2 H2 121.4 . . ? C4 C3 C2 120.3(5) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 119.4(5) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 121.7(4) . . ? N1 C5 C6 115.7(4) . . ? C4 C5 C6 122.6(4) . . ? N2 C6 C7 121.0(5) . . ? N2 C6 C5 114.1(4) . . ? C7 C6 C5 125.0(5) . . ? C8 C7 C6 118.9(5) . . ? C8 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? C7 C8 C9 119.6(5) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 119.5(5) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? N2 C10 C9 120.7(5) . . ? N2 C10 C11 114.3(4) . . ? C9 C10 C11 125.0(4) . . ? O2 C11 O3 113.3(4) . . ? O2 C11 C10 110.7(4) . . ? O3 C11 C10 104.3(4) . . ? O2 C11 C13 109.2(4) . . ? O3 C11 C13 111.2(4) . . ? C10 C11 C13 107.8(4) . . ? O3 C12 H12A 109.5 . . ? O3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 C14 120.3(4) . . ? N3 C13 C11 113.3(4) . . ? C14 C13 C11 126.4(5) . . ? C15 C14 C13 119.5(5) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 119.4(5) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C17 C16 C15 119.4(5) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? N3 C17 C16 121.0(5) . . ? N3 C17 C18 112.6(5) . . ? C16 C17 C18 126.4(5) . . ? N4 C18 C19 122.4(6) . . ? N4 C18 C17 114.5(5) . . ? C19 C18 C17 122.9(5) . . ? C20 C19 C18 117.8(6) . . ? C20 C19 H19 121.1 . . ? C18 C19 H19 121.1 . . ? C21 C20 C19 119.5(6) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C22 C21 C20 119.1(6) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? N4 C22 C21 123.2(6) . . ? N4 C22 H22 118.4 . . ? C21 C22 H22 118.4 . . ? N5 C23 C24 122.6(5) . . ? N5 C23 H23 118.7 . . ? C24 C23 H23 118.7 . . ? C25 C24 C23 119.4(5) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C24 C25 C26 118.6(5) . . ? C24 C25 H25 120.7 . . ? C26 C25 H25 120.7 . . ? C25 C26 C27 119.6(5) . . ? C25 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? N5 C27 C26 121.0(5) . . ? N5 C27 C28 116.7(5) . . ? C26 C27 C28 122.3(5) . . ? N6 C28 C29 120.4(5) . . ? N6 C28 C27 114.1(4) . . ? C29 C28 C27 125.5(5) . . ? C28 C29 C30 119.0(5) . . ? C28 C29 H29 120.5 . . ? C30 C29 H29 120.5 . . ? C31 C30 C29 120.4(5) . . ? C31 C30 H30 119.8 . . ? C29 C30 H30 119.8 . . ? C30 C31 C32 118.4(5) . . ? C30 C31 H31 120.8 . . ? C32 C31 H31 120.8 . . ? N6 C32 C31 121.5(5) . . ? N6 C32 C33 113.7(4) . . ? C31 C32 C33 124.8(5) . . ? O1 C33 O4 112.5(4) . . ? O1 C33 C32 111.7(4) . . ? O4 C33 C32 103.3(4) . . ? O1 C33 C35 109.8(4) . . ? O4 C33 C35 110.3(4) . . ? C32 C33 C35 109.1(4) . . ? O4 C34 H34A 109.5 . . ? O4 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O4 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N7 C35 C36 120.9(4) . . ? N7 C35 C33 113.7(4) . . ? C36 C35 C33 125.3(4) . . ? C37 C36 C35 118.8(5) . . ? C37 C36 H36 120.6 . . ? C35 C36 H36 120.6 . . ? C36 C37 C38 120.2(5) . . ? C36 C37 H37 119.9 . . ? C38 C37 H37 119.9 . . ? C37 C38 C39 118.8(5) . . ? C37 C38 H38 120.6 . . ? C39 C38 H38 120.6 . . ? N7 C39 C38 119.8(5) . . ? N7 C39 C40 114.0(4) . . ? C38 C39 C40 126.2(5) . . ? N8 C40 C41 121.4(5) . . ? N8 C40 C39 115.1(4) . . ? C41 C40 C39 123.5(5) . . ? C42 C41 C40 119.7(5) . . ? C42 C41 H41 120.2 . . ? C40 C41 H41 120.2 . . ? C41 C42 C43 118.9(5) . . ? C41 C42 H42 120.5 . . ? C43 C42 H42 120.5 . . ? C44 C43 C42 118.1(5) . . ? C44 C43 H43 121.0 . . ? C42 C43 H43 121.0 . . ? N8 C44 C43 123.8(5) . . ? N8 C44 H44 118.1 . . ? C43 C44 H44 118.1 . . ? O13 Cl1 O12 110.8(4) . . ? O13 Cl1 O14 109.2(4) . . ? O12 Cl1 O14 111.6(3) . . ? O13 Cl1 O11 110.3(5) . . ? O12 Cl1 O11 108.9(3) . . ? O14 Cl1 O11 105.9(4) . . ? O23 Cl2 O21 111.9(6) . . ? O23 Cl2 O22 110.3(4) . . ? O21 Cl2 O22 109.4(4) . . ? O23 Cl2 O24 107.6(6) . . ? O21 Cl2 O24 105.6(4) . . ? O22 Cl2 O24 111.8(4) . . ? O1 Fe1 O2 81.41(12) . . ? O1 Fe1 N2 119.20(14) . . ? O2 Fe1 N2 76.33(15) . . ? O1 Fe1 N7 76.13(14) . . ? O2 Fe1 N7 119.54(16) . . ? N2 Fe1 N7 160.82(16) . . ? O1 Fe1 N8 148.46(15) . . ? O2 Fe1 N8 103.47(14) . . ? N2 Fe1 N8 92.00(15) . . ? N7 Fe1 N8 74.47(15) . . ? O1 Fe1 N1 106.39(14) . . ? O2 Fe1 N1 149.43(14) . . ? N2 Fe1 N1 74.13(15) . . ? N7 Fe1 N1 90.99(16) . . ? N8 Fe1 N1 85.36(16) . . ? O2 Fe2 N3 76.17(14) . . ? O2 Fe2 O1 81.46(12) . . ? N3 Fe2 O1 123.84(15) . . ? O2 Fe2 N6 121.19(14) . . ? N3 Fe2 N6 157.25(15) . . ? O1 Fe2 N6 76.05(14) . . ? O2 Fe2 N4 147.61(16) . . ? N3 Fe2 N4 74.32(16) . . ? O1 Fe2 N4 104.29(15) . . ? N6 Fe2 N4 90.89(16) . . ? O2 Fe2 N5 106.56(15) . . ? N3 Fe2 N5 87.68(16) . . ? O1 Fe2 N5 148.38(15) . . ? N6 Fe2 N5 73.73(15) . . ? N4 Fe2 N5 85.36(16) . . ? C5 N1 C1 118.2(4) . . ? C5 N1 Fe1 114.4(3) . . ? C1 N1 Fe1 127.0(3) . . ? C6 N2 C10 120.2(4) . . ? C6 N2 Fe1 120.5(3) . . ? C10 N2 Fe1 118.3(3) . . ? C17 N3 C13 120.3(4) . . ? C17 N3 Fe2 119.4(3) . . ? C13 N3 Fe2 117.4(3) . . ? C22 N4 C18 117.9(5) . . ? C22 N4 Fe2 126.7(4) . . ? C18 N4 Fe2 115.2(3) . . ? C27 N5 C23 118.7(5) . . ? C27 N5 Fe2 113.3(3) . . ? C23 N5 Fe2 127.2(4) . . ? C32 N6 C28 120.2(4) . . ? C32 N6 Fe2 119.1(4) . . ? C28 N6 Fe2 120.1(3) . . ? C35 N7 C39 121.5(4) . . ? C35 N7 Fe1 117.5(3) . . ? C39 N7 Fe1 119.2(3) . . ? C44 N8 C40 118.0(4) . . ? C44 N8 Fe1 126.7(3) . . ? C40 N8 Fe1 115.3(3) . . ? C33 O1 Fe1 119.7(3) . . ? C33 O1 Fe2 118.9(3) . . ? Fe1 O1 Fe2 98.44(12) . . ? C11 O2 Fe2 120.1(3) . . ? C11 O2 Fe1 119.1(3) . . ? Fe2 O2 Fe1 98.67(13) . . ? C11 O3 C12 113.6(4) . . ? C33 O4 C34 113.5(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 N1 C1 C2 C3 0.2(8) . . . . ? C1 C2 C3 C4 -0.5(8) . . . . ? C2 C3 C4 C5 0.3(8) . . . . ? C3 C4 C5 N1 0.3(8) . . . . ? C3 C4 C5 C6 -180.0(5) . . . . ? N1 C5 C6 N2 -0.1(6) . . . . ? C4 C5 C6 N2 -179.8(4) . . . . ? N1 C5 C6 C7 179.4(5) . . . . ? C4 C5 C6 C7 -0.3(8) . . . . ? N2 C6 C7 C8 1.4(8) . . . . ? C5 C6 C7 C8 -178.1(5) . . . . ? C6 C7 C8 C9 1.4(8) . . . . ? C7 C8 C9 C10 -3.1(8) . . . . ? C8 C9 C10 N2 2.0(8) . . . . ? C8 C9 C10 C11 179.7(5) . . . . ? N2 C10 C11 O2 0.1(6) . . . . ? C9 C10 C11 O2 -177.7(5) . . . . ? N2 C10 C11 O3 122.3(4) . . . . ? C9 C10 C11 O3 -55.5(6) . . . . ? N2 C10 C11 C13 -119.4(4) . . . . ? C9 C10 C11 C13 62.8(6) . . . . ? O2 C11 C13 N3 -17.6(6) . . . . ? O3 C11 C13 N3 -143.5(4) . . . . ? C10 C11 C13 N3 102.8(5) . . . . ? O2 C11 C13 C14 162.7(5) . . . . ? O3 C11 C13 C14 36.9(7) . . . . ? C10 C11 C13 C14 -76.9(6) . . . . ? N3 C13 C14 C15 -1.2(8) . . . . ? C11 C13 C14 C15 178.5(6) . . . . ? C13 C14 C15 C16 -0.6(9) . . . . ? C14 C15 C16 C17 0.8(9) . . . . ? C15 C16 C17 N3 0.8(9) . . . . ? C15 C16 C17 C18 -178.2(6) . . . . ? N3 C17 C18 N4 14.8(7) . . . . ? C16 C17 C18 N4 -166.1(5) . . . . ? N3 C17 C18 C19 -160.5(5) . . . . ? C16 C17 C18 C19 18.6(9) . . . . ? N4 C18 C19 C20 0.0(9) . . . . ? C17 C18 C19 C20 175.0(6) . . . . ? C18 C19 C20 C21 -0.4(10) . . . . ? C19 C20 C21 C22 0.8(11) . . . . ? C20 C21 C22 N4 -0.7(11) . . . . ? N5 C23 C24 C25 -2.4(9) . . . . ? C23 C24 C25 C26 2.2(9) . . . . ? C24 C25 C26 C27 0.5(8) . . . . ? C25 C26 C27 N5 -3.3(8) . . . . ? C25 C26 C27 C28 176.0(5) . . . . ? N5 C27 C28 N6 -4.9(6) . . . . ? C26 C27 C28 N6 175.8(4) . . . . ? N5 C27 C28 C29 173.0(5) . . . . ? C26 C27 C28 C29 -6.3(8) . . . . ? N6 C28 C29 C30 -1.6(8) . . . . ? C27 C28 C29 C30 -179.4(5) . . . . ? C28 C29 C30 C31 -0.8(8) . . . . ? C29 C30 C31 C32 2.0(8) . . . . ? C30 C31 C32 N6 -0.8(8) . . . . ? C30 C31 C32 C33 177.8(5) . . . . ? N6 C32 C33 O1 -3.7(6) . . . . ? C31 C32 C33 O1 177.5(5) . . . . ? N6 C32 C33 O4 -124.8(4) . . . . ? C31 C32 C33 O4 56.4(6) . . . . ? N6 C32 C33 C35 117.9(4) . . . . ? C31 C32 C33 C35 -60.9(6) . . . . ? O1 C33 C35 N7 14.7(6) . . . . ? O4 C33 C35 N7 139.2(5) . . . . ? C32 C33 C35 N7 -108.1(5) . . . . ? O1 C33 C35 C36 -169.0(5) . . . . ? O4 C33 C35 C36 -44.5(7) . . . . ? C32 C33 C35 C36 68.3(7) . . . . ? N7 C35 C36 C37 0.4(9) . . . . ? C33 C35 C36 C37 -175.7(5) . . . . ? C35 C36 C37 C38 1.8(9) . . . . ? C36 C37 C38 C39 -2.9(9) . . . . ? C37 C38 C39 N7 1.9(8) . . . . ? C37 C38 C39 C40 -178.6(6) . . . . ? N7 C39 C40 N8 -11.5(7) . . . . ? C38 C39 C40 N8 169.0(5) . . . . ? N7 C39 C40 C41 168.6(5) . . . . ? C38 C39 C40 C41 -10.9(9) . . . . ? N8 C40 C41 C42 2.1(9) . . . . ? C39 C40 C41 C42 -178.0(5) . . . . ? C40 C41 C42 C43 -3.2(9) . . . . ? C41 C42 C43 C44 1.9(9) . . . . ? C42 C43 C44 N8 0.6(9) . . . . ? C4 C5 N1 C1 -0.6(7) . . . . ? C6 C5 N1 C1 179.7(4) . . . . ? C4 C5 N1 Fe1 172.3(4) . . . . ? C6 C5 N1 Fe1 -7.5(5) . . . . ? C2 C1 N1 C5 0.3(7) . . . . ? C2 C1 N1 Fe1 -171.5(4) . . . . ? O1 Fe1 N1 C5 125.3(3) . . . . ? O2 Fe1 N1 C5 24.2(5) . . . . ? N2 Fe1 N1 C5 8.9(3) . . . . ? N7 Fe1 N1 C5 -158.9(3) . . . . ? N8 Fe1 N1 C5 -84.6(3) . . . . ? O1 Fe1 N1 C1 -62.6(4) . . . . ? O2 Fe1 N1 C1 -163.6(3) . . . . ? N2 Fe1 N1 C1 -179.0(4) . . . . ? N7 Fe1 N1 C1 13.2(4) . . . . ? N8 Fe1 N1 C1 87.6(4) . . . . ? C7 C6 N2 C10 -2.5(7) . . . . ? C5 C6 N2 C10 177.1(4) . . . . ? C7 C6 N2 Fe1 -170.9(4) . . . . ? C5 C6 N2 Fe1 8.7(5) . . . . ? C9 C10 N2 C6 0.8(7) . . . . ? C11 C10 N2 C6 -177.1(4) . . . . ? C9 C10 N2 Fe1 169.4(4) . . . . ? C11 C10 N2 Fe1 -8.5(5) . . . . ? O1 Fe1 N2 C6 -109.7(3) . . . . ? O2 Fe1 N2 C6 178.5(4) . . . . ? N7 Fe1 N2 C6 30.8(7) . . . . ? N8 Fe1 N2 C6 75.1(4) . . . . ? N1 Fe1 N2 C6 -9.5(3) . . . . ? O1 Fe1 N2 C10 81.7(4) . . . . ? O2 Fe1 N2 C10 9.9(3) . . . . ? N7 Fe1 N2 C10 -137.8(5) . . . . ? N8 Fe1 N2 C10 -93.5(4) . . . . ? N1 Fe1 N2 C10 -178.1(4) . . . . ? C16 C17 N3 C13 -2.6(8) . . . . ? C18 C17 N3 C13 176.5(5) . . . . ? C16 C17 N3 Fe2 157.6(4) . . . . ? C18 C17 N3 Fe2 -23.2(6) . . . . ? C14 C13 N3 C17 2.8(8) . . . . ? C11 C13 N3 C17 -176.9(5) . . . . ? C14 C13 N3 Fe2 -157.8(4) . . . . ? C11 C13 N3 Fe2 22.5(6) . . . . ? O2 Fe2 N3 C17 -176.0(4) . . . . ? O1 Fe2 N3 C17 114.5(4) . . . . ? N6 Fe2 N3 C17 -33.6(7) . . . . ? N4 Fe2 N3 C17 17.5(4) . . . . ? N5 Fe2 N3 C17 -68.3(4) . . . . ? O2 Fe2 N3 C13 -15.1(3) . . . . ? O1 Fe2 N3 C13 -84.7(4) . . . . ? N6 Fe2 N3 C13 127.3(4) . . . . ? N4 Fe2 N3 C13 178.4(4) . . . . ? N5 Fe2 N3 C13 92.5(4) . . . . ? C21 C22 N4 C18 0.3(9) . . . . ? C21 C22 N4 Fe2 -173.4(5) . . . . ? C19 C18 N4 C22 0.1(8) . . . . ? C17 C18 N4 C22 -175.3(5) . . . . ? C19 C18 N4 Fe2 174.5(5) . . . . ? C17 C18 N4 Fe2 -0.9(6) . . . . ? O2 Fe2 N4 C22 140.8(4) . . . . ? N3 Fe2 N4 C22 165.8(5) . . . . ? O1 Fe2 N4 C22 44.1(5) . . . . ? N6 Fe2 N4 C22 -31.7(5) . . . . ? N5 Fe2 N4 C22 -105.3(5) . . . . ? O2 Fe2 N4 C18 -33.1(6) . . . . ? N3 Fe2 N4 C18 -8.1(4) . . . . ? O1 Fe2 N4 C18 -129.8(4) . . . . ? N6 Fe2 N4 C18 154.4(4) . . . . ? N5 Fe2 N4 C18 80.8(4) . . . . ? C26 C27 N5 C23 3.2(7) . . . . ? C28 C27 N5 C23 -176.1(4) . . . . ? C26 C27 N5 Fe2 -167.3(4) . . . . ? C28 C27 N5 Fe2 13.4(5) . . . . ? C24 C23 N5 C27 -0.4(8) . . . . ? C24 C23 N5 Fe2 168.6(4) . . . . ? O2 Fe2 N5 C27 -131.2(3) . . . . ? N3 Fe2 N5 C27 154.0(3) . . . . ? O1 Fe2 N5 C27 -30.4(5) . . . . ? N6 Fe2 N5 C27 -12.8(3) . . . . ? N4 Fe2 N5 C27 79.5(3) . . . . ? O2 Fe2 N5 C23 59.3(4) . . . . ? N3 Fe2 N5 C23 -15.5(4) . . . . ? O1 Fe2 N5 C23 160.1(4) . . . . ? N6 Fe2 N5 C23 177.8(5) . . . . ? N4 Fe2 N5 C23 -90.0(4) . . . . ? C31 C32 N6 C28 -1.6(7) . . . . ? C33 C32 N6 C28 179.7(4) . . . . ? C31 C32 N6 Fe2 -173.4(4) . . . . ? C33 C32 N6 Fe2 7.8(5) . . . . ? C29 C28 N6 C32 2.8(7) . . . . ? C27 C28 N6 C32 -179.2(4) . . . . ? C29 C28 N6 Fe2 174.6(4) . . . . ? C27 C28 N6 Fe2 -7.4(5) . . . . ? O2 Fe2 N6 C32 -77.6(4) . . . . ? N3 Fe2 N6 C32 146.3(4) . . . . ? O1 Fe2 N6 C32 -6.8(3) . . . . ? N4 Fe2 N6 C32 97.7(4) . . . . ? N5 Fe2 N6 C32 -177.4(4) . . . . ? O2 Fe2 N6 C28 110.5(3) . . . . ? N3 Fe2 N6 C28 -25.6(6) . . . . ? O1 Fe2 N6 C28 -178.7(4) . . . . ? N4 Fe2 N6 C28 -74.2(4) . . . . ? N5 Fe2 N6 C28 10.7(3) . . . . ? C36 C35 N7 C39 -1.5(9) . . . . ? C33 C35 N7 C39 175.0(5) . . . . ? C36 C35 N7 Fe1 163.0(5) . . . . ? C33 C35 N7 Fe1 -20.5(6) . . . . ? C38 C39 N7 C35 0.3(8) . . . . ? C40 C39 N7 C35 -179.2(5) . . . . ? C38 C39 N7 Fe1 -163.9(4) . . . . ? C40 C39 N7 Fe1 16.6(6) . . . . ? O1 Fe1 N7 C35 14.9(4) . . . . ? O2 Fe1 N7 C35 86.4(4) . . . . ? N2 Fe1 N7 C35 -130.2(5) . . . . ? N8 Fe1 N7 C35 -176.7(4) . . . . ? N1 Fe1 N7 C35 -91.8(4) . . . . ? O1 Fe1 N7 C39 179.7(4) . . . . ? O2 Fe1 N7 C39 -108.8(4) . . . . ? N2 Fe1 N7 C39 34.6(7) . . . . ? N8 Fe1 N7 C39 -11.8(4) . . . . ? N1 Fe1 N7 C39 73.1(4) . . . . ? C43 C44 N8 C40 -1.8(9) . . . . ? C43 C44 N8 Fe1 176.7(4) . . . . ? C41 C40 N8 C44 0.4(8) . . . . ? C39 C40 N8 C44 -179.5(5) . . . . ? C41 C40 N8 Fe1 -178.2(4) . . . . ? C39 C40 N8 Fe1 1.9(6) . . . . ? O1 Fe1 N8 C44 -151.8(4) . . . . ? O2 Fe1 N8 C44 -56.3(5) . . . . ? N2 Fe1 N8 C44 20.2(5) . . . . ? N7 Fe1 N8 C44 -173.6(5) . . . . ? N1 Fe1 N8 C44 94.0(5) . . . . ? O1 Fe1 N8 C40 26.6(5) . . . . ? O2 Fe1 N8 C40 122.2(4) . . . . ? N2 Fe1 N8 C40 -161.4(4) . . . . ? N7 Fe1 N8 C40 4.8(4) . . . . ? N1 Fe1 N8 C40 -87.5(4) . . . . ? O4 C33 O1 Fe1 -125.8(3) . . . . ? C32 C33 O1 Fe1 118.7(4) . . . . ? C35 C33 O1 Fe1 -2.5(5) . . . . ? O4 C33 O1 Fe2 113.7(4) . . . . ? C32 C33 O1 Fe2 -1.9(5) . . . . ? C35 C33 O1 Fe2 -123.0(4) . . . . ? O2 Fe1 O1 C33 -129.2(3) . . . . ? N2 Fe1 O1 C33 161.8(3) . . . . ? N7 Fe1 O1 C33 -5.7(3) . . . . ? N8 Fe1 O1 C33 -27.4(5) . . . . ? N1 Fe1 O1 C33 81.2(3) . . . . ? O2 Fe1 O1 Fe2 1.19(15) . . . . ? N2 Fe1 O1 Fe2 -67.8(2) . . . . ? N7 Fe1 O1 Fe2 124.61(18) . . . . ? N8 Fe1 O1 Fe2 103.0(3) . . . . ? N1 Fe1 O1 Fe2 -148.49(15) . . . . ? O2 Fe2 O1 C33 129.7(3) . . . . ? N3 Fe2 O1 C33 -163.4(3) . . . . ? N6 Fe2 O1 C33 4.4(3) . . . . ? N4 Fe2 O1 C33 -82.9(3) . . . . ? N5 Fe2 O1 C33 21.9(5) . . . . ? O2 Fe2 O1 Fe1 -1.19(15) . . . . ? N3 Fe2 O1 Fe1 65.8(2) . . . . ? N6 Fe2 O1 Fe1 -126.42(17) . . . . ? N4 Fe2 O1 Fe1 146.26(16) . . . . ? N5 Fe2 O1 Fe1 -109.0(2) . . . . ? O3 C11 O2 Fe2 130.1(3) . . . . ? C10 C11 O2 Fe2 -113.1(4) . . . . ? C13 C11 O2 Fe2 5.5(5) . . . . ? O3 C11 O2 Fe1 -108.4(4) . . . . ? C10 C11 O2 Fe1 8.4(5) . . . . ? C13 C11 O2 Fe1 127.0(3) . . . . ? N3 Fe2 O2 C11 4.2(3) . . . . ? O1 Fe2 O2 C11 132.3(3) . . . . ? N6 Fe2 O2 C11 -159.8(3) . . . . ? N4 Fe2 O2 C11 29.0(5) . . . . ? N5 Fe2 O2 C11 -79.1(4) . . . . ? N3 Fe2 O2 Fe1 -126.89(18) . . . . ? O1 Fe2 O2 Fe1 1.19(15) . . . . ? N6 Fe2 O2 Fe1 69.1(2) . . . . ? N4 Fe2 O2 Fe1 -102.1(3) . . . . ? N5 Fe2 O2 Fe1 149.81(15) . . . . ? O1 Fe1 O2 C11 -132.9(3) . . . . ? N2 Fe1 O2 C11 -10.0(3) . . . . ? N7 Fe1 O2 C11 158.4(3) . . . . ? N8 Fe1 O2 C11 78.8(3) . . . . ? N1 Fe1 O2 C11 -25.2(5) . . . . ? O1 Fe1 O2 Fe2 -1.20(15) . . . . ? N2 Fe1 O2 Fe2 121.80(17) . . . . ? N7 Fe1 O2 Fe2 -69.84(19) . . . . ? N8 Fe1 O2 Fe2 -149.42(15) . . . . ? N1 Fe1 O2 Fe2 106.6(3) . . . . ? O2 C11 O3 C12 -56.7(5) . . . . ? C10 C11 O3 C12 -177.3(4) . . . . ? C13 C11 O3 C12 66.8(5) . . . . ? O1 C33 O4 C34 56.7(5) . . . . ? C32 C33 O4 C34 177.2(4) . . . . ? C35 C33 O4 C34 -66.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.847 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.081 # Attachment '3-Co.cif' data_aja0712 _database_code_depnum_ccdc_archive 'CCDC 774565' #TrackingRef '3-Co.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common aja0712 _chemical_melting_point ? _chemical_formula_moiety 'C21 H18 Co N4 O3, 2(Cl O4)' _chemical_formula_sum 'C21 H18 Cl2 Co N4 O11' _chemical_formula_weight 632.22 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 11.3538(3) _cell_length_b 15.1853(5) _cell_length_c 29.0604(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5010.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 17313 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2568 _exptl_absorpt_coefficient_mu 0.967 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7284 _exptl_absorpt_correction_T_max 0.7668 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; The crystals diffracted weakly as is reflected by the high Rint values. ; _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20942 _diffrn_reflns_av_R_equivalents 0.1389 _diffrn_reflns_av_sigmaI/netI 0.1411 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5707 _reflns_number_gt 2616 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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. One perchlorate ion site is disordered and was modelled with two components of 60/40% occupancy with restrained geometry and adps. ; _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^)+(0.1138P)^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 SHELXL _refine_ls_extinction_coef 0.0024(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5707 _refine_ls_number_parameters 399 _refine_ls_number_restraints 138 _refine_ls_R_factor_all 0.1847 _refine_ls_R_factor_gt 0.0738 _refine_ls_wR_factor_ref 0.2308 _refine_ls_wR_factor_gt 0.1820 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.040 _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 C1 C 0.4440(8) 0.2834(4) 0.1954(2) 0.071(2) Uani 1 1 d . . . C2 C 0.5547(6) 0.2670(4) 0.1685(2) 0.0573(18) Uani 1 1 d . . . C3 C 0.6456(8) 0.3257(4) 0.1761(3) 0.080(2) Uani 1 1 d . . . H3 H 0.6388 0.3714 0.1982 0.096 Uiso 1 1 calc R . . C4 C 0.7455(9) 0.3159(5) 0.1506(3) 0.095(3) Uani 1 1 d . . . H4 H 0.8070 0.3579 0.1535 0.114 Uiso 1 1 calc R . . C5 C 0.7594(7) 0.2465(5) 0.1208(3) 0.076(2) Uani 1 1 d . . . H5 H 0.8299 0.2394 0.1035 0.091 Uiso 1 1 calc R . . C6 C 0.6668(6) 0.1869(4) 0.11665(19) 0.0534(16) Uani 1 1 d . . . C7 C 0.6760(6) 0.1061(4) 0.08758(17) 0.0508(15) Uani 1 1 d . . . C8 C 0.7749(6) 0.0866(5) 0.0622(2) 0.0642(19) Uani 1 1 d . . . H8 H 0.8391 0.1267 0.0610 0.077 Uiso 1 1 calc R . . C9 C 0.7793(7) 0.0081(6) 0.0385(2) 0.082(2) Uani 1 1 d . . . H9 H 0.8473 -0.0077 0.0214 0.098 Uiso 1 1 calc R . . C10 C 0.6838(8) -0.0465(6) 0.0403(2) 0.084(2) Uani 1 1 d . . . H10 H 0.6846 -0.1014 0.0247 0.101 Uiso 1 1 calc R . . C11 C 0.5875(6) -0.0213(5) 0.0648(2) 0.079(2) Uani 1 1 d . . . H11 H 0.5212 -0.0595 0.0652 0.095 Uiso 1 1 calc R . . C12 C 0.3231(7) 0.2525(4) 0.18290(18) 0.0599(18) Uani 1 1 d . . . C13 C 0.2267(9) 0.3041(5) 0.1971(2) 0.081(2) Uani 1 1 d . . . H13 H 0.2395 0.3580 0.2130 0.098 Uiso 1 1 calc R . . C14 C 0.1161(10) 0.2767(7) 0.1882(3) 0.103(3) Uani 1 1 d . . . H14 H 0.0506 0.3124 0.1963 0.123 Uiso 1 1 calc R . . C15 C 0.0994(8) 0.1981(7) 0.1676(3) 0.089(2) Uani 1 1 d . . . H15 H 0.0216 0.1778 0.1621 0.107 Uiso 1 1 calc R . . C16 C 0.1938(6) 0.1467(5) 0.15452(19) 0.0589(17) Uani 1 1 d . . . C17 C 0.1802(6) 0.0615(5) 0.13152(19) 0.0590(17) Uani 1 1 d . . . C18 C 0.0735(7) 0.0197(7) 0.1253(3) 0.084(2) Uani 1 1 d . . . H18 H 0.0036 0.0445 0.1377 0.101 Uiso 1 1 calc R . . C19 C 0.0685(8) -0.0577(7) 0.1012(3) 0.096(3) Uani 1 1 d . . . H19 H -0.0048 -0.0865 0.0966 0.115 Uiso 1 1 calc R . . C20 C 0.1694(9) -0.0930(5) 0.0839(3) 0.089(3) Uani 1 1 d . . . H20 H 0.1682 -0.1457 0.0664 0.107 Uiso 1 1 calc R . . C21 C 0.2711(7) -0.0502(5) 0.0926(2) 0.074(2) Uani 1 1 d . . . H21 H 0.3417 -0.0770 0.0819 0.089 Uiso 1 1 calc R . . N1 N 0.5645(4) 0.1982(3) 0.13955(15) 0.0478(12) Uani 1 1 d . . . N2 N 0.5809(4) 0.0535(3) 0.08816(14) 0.0493(12) Uani 1 1 d . . . N3 N 0.3055(5) 0.1760(3) 0.16099(14) 0.0522(13) Uani 1 1 d . . . N4 N 0.2815(5) 0.0261(3) 0.11469(16) 0.0544(13) Uani 1 1 d . . . O1 O 0.4507(5) 0.3328(3) 0.22848(16) 0.0973(18) Uani 1 1 d . . . O2 O 0.3877(4) 0.1696(3) 0.06492(12) 0.0668(12) Uani 1 1 d . . . H2A H 0.4444 0.1754 0.0455 0.080 Uiso 1 1 d . . . H2B H 0.3380 0.2106 0.0584 0.080 Uiso 1 1 d . . . O3 O 0.4833(4) 0.0222(3) 0.18068(12) 0.0600(11) Uani 1 1 d . . . H3A H 0.5428 0.0172 0.1992 0.072 Uiso 1 1 d . . . H3B H 0.4340 -0.0170 0.1889 0.072 Uiso 1 1 d . . . Cl1 Cl 0.28513(16) 0.06653(10) 0.27814(5) 0.0584(5) Uani 1 1 d D . . O4 O 0.3119(6) 0.0013(3) 0.24622(17) 0.113(2) Uani 1 1 d D . . O5 O 0.1781(5) 0.1068(5) 0.2677(2) 0.134(3) Uani 1 1 d D . . O6 O 0.2799(7) 0.0329(4) 0.32258(16) 0.142(3) Uani 1 1 d D . . O7 O 0.3698(7) 0.1354(4) 0.2737(2) 0.139(3) Uani 1 1 d D . . Co1 Co 0.43518(7) 0.10259(5) 0.12609(2) 0.0436(3) Uani 1 1 d . . . Cl2 Cl 0.0786(6) 0.2207(4) 0.0196(2) 0.0547(9) Uani 0.598(10) 1 d PDU A 1 O8 O 0.0858(11) 0.1370(6) 0.0379(4) 0.149(5) Uani 0.598(10) 1 d PDU A 1 O9 O 0.1829(10) 0.2666(10) 0.0283(5) 0.200(7) Uani 0.598(10) 1 d PDU A 1 O10 O 0.0579(10) 0.2179(7) -0.0272(2) 0.118(4) Uani 0.598(10) 1 d PDU A 1 O11 O -0.0111(9) 0.2688(7) 0.0431(4) 0.136(5) Uani 0.598(10) 1 d PDU A 1 Cl2A Cl 0.0743(9) 0.2331(6) 0.0251(3) 0.0552(11) Uani 0.402(10) 1 d PDU A 2 O8A O 0.0626(14) 0.3160(7) 0.0055(5) 0.122(6) Uani 0.402(10) 1 d PDU A 2 O9A O 0.0073(14) 0.1722(10) -0.0002(5) 0.133(7) Uani 0.402(10) 1 d PDU A 2 O10A O 0.0356(17) 0.2355(12) 0.0702(4) 0.169(9) Uani 0.402(10) 1 d PDU A 2 O11A O 0.1927(11) 0.2035(13) 0.0221(7) 0.173(9) Uani 0.402(10) 1 d PDU A 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 C1 0.106(7) 0.054(4) 0.053(4) -0.010(3) 0.000(4) 0.017(4) C2 0.082(5) 0.035(3) 0.055(3) 0.000(3) -0.011(3) 0.003(4) C3 0.094(7) 0.046(4) 0.101(5) -0.005(4) -0.020(5) -0.014(5) C4 0.102(8) 0.063(5) 0.122(7) 0.004(5) -0.013(6) -0.029(5) C5 0.058(5) 0.069(5) 0.101(5) 0.008(4) -0.002(4) -0.019(4) C6 0.057(4) 0.047(4) 0.056(3) 0.010(3) -0.001(3) -0.006(3) C7 0.048(4) 0.063(4) 0.042(3) 0.006(3) -0.004(3) 0.008(3) C8 0.041(4) 0.087(5) 0.065(4) 0.004(4) 0.007(3) 0.002(4) C9 0.060(5) 0.122(7) 0.063(4) -0.015(4) 0.018(4) 0.018(5) C10 0.077(6) 0.095(6) 0.080(5) -0.044(4) 0.007(4) 0.007(5) C11 0.049(5) 0.092(5) 0.095(5) -0.042(4) 0.016(4) -0.009(4) C12 0.076(5) 0.058(4) 0.046(3) 0.001(3) 0.005(3) 0.022(4) C13 0.101(7) 0.079(5) 0.065(4) -0.009(4) 0.017(5) 0.036(5) C14 0.097(8) 0.122(8) 0.089(6) 0.009(5) 0.030(6) 0.052(7) C15 0.066(6) 0.119(7) 0.081(5) 0.017(5) 0.018(4) 0.028(6) C16 0.050(4) 0.075(5) 0.052(3) 0.019(3) 0.011(3) 0.022(4) C17 0.050(5) 0.073(5) 0.054(3) 0.020(3) 0.003(3) 0.000(4) C18 0.041(5) 0.116(7) 0.095(6) 0.032(5) -0.006(4) -0.008(5) C19 0.066(6) 0.116(8) 0.107(6) 0.037(6) -0.017(5) -0.040(6) C20 0.075(7) 0.076(5) 0.117(6) -0.006(4) -0.008(5) -0.034(5) C21 0.058(5) 0.074(5) 0.091(5) -0.014(4) -0.006(4) -0.016(4) N1 0.054(3) 0.043(3) 0.046(2) 0.006(2) -0.007(2) 0.002(2) N2 0.045(3) 0.052(3) 0.050(3) -0.012(2) 0.001(2) -0.003(3) N3 0.058(4) 0.056(3) 0.043(2) 0.003(2) 0.006(2) 0.013(3) N4 0.047(3) 0.056(3) 0.061(3) 0.003(2) 0.003(3) -0.001(3) O1 0.135(5) 0.082(4) 0.075(3) -0.035(3) -0.008(3) 0.014(3) O2 0.060(3) 0.086(3) 0.054(2) 0.023(2) 0.005(2) 0.010(3) O3 0.057(3) 0.063(3) 0.060(2) 0.0158(19) 0.000(2) 0.000(2) Cl1 0.0638(12) 0.0565(10) 0.0549(9) 0.0015(7) 0.0083(8) 0.0077(9) O4 0.166(6) 0.073(3) 0.099(4) -0.019(3) 0.066(4) -0.020(4) O5 0.087(5) 0.186(7) 0.129(5) 0.026(4) 0.005(4) 0.055(5) O6 0.257(9) 0.101(4) 0.066(3) 0.024(3) 0.049(4) 0.077(5) O7 0.149(6) 0.117(5) 0.152(6) -0.022(4) -0.013(5) -0.061(5) Co1 0.0436(6) 0.0460(5) 0.0412(4) -0.0025(3) 0.0025(3) 0.0025(4) Cl2 0.0490(13) 0.0584(16) 0.0568(14) 0.0005(12) -0.0030(11) 0.0056(12) O8 0.190(8) 0.115(7) 0.143(7) 0.034(6) 0.011(6) 0.034(6) O9 0.163(9) 0.198(10) 0.238(10) -0.017(7) -0.023(7) -0.031(7) O10 0.142(7) 0.133(7) 0.081(5) 0.002(5) -0.003(5) 0.017(5) O11 0.118(7) 0.133(7) 0.155(7) -0.026(6) 0.026(6) 0.044(6) Cl2A 0.0507(15) 0.0578(17) 0.0571(16) -0.0001(14) -0.0016(13) 0.0035(14) O8A 0.138(9) 0.107(8) 0.120(8) 0.014(6) -0.009(6) 0.000(7) O9A 0.132(9) 0.135(9) 0.133(9) -0.033(7) -0.010(7) -0.031(7) O10A 0.180(11) 0.176(11) 0.150(10) 0.007(7) 0.002(7) 0.004(8) O11A 0.136(11) 0.185(11) 0.197(11) -0.023(8) -0.029(7) 0.020(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 C1 O1 1.221(7) . ? C1 C12 1.496(10) . ? C1 C2 1.500(10) . ? C2 N1 1.347(7) . ? C2 C3 1.382(9) . ? C3 C4 1.363(11) . ? C3 H3 0.9500 . ? C4 C5 1.372(11) . ? C4 H4 0.9500 . ? C5 C6 1.393(9) . ? C5 H5 0.9500 . ? C6 N1 1.349(7) . ? C6 C7 1.494(8) . ? C7 N2 1.343(7) . ? C7 C8 1.376(9) . ? C8 C9 1.377(9) . ? C8 H8 0.9500 . ? C9 C10 1.366(10) . ? C9 H9 0.9500 . ? C10 C11 1.359(9) . ? C10 H10 0.9500 . ? C11 N2 1.325(8) . ? C11 H11 0.9500 . ? C12 N3 1.340(8) . ? C12 C13 1.408(10) . ? C13 C14 1.348(12) . ? C13 H13 0.9500 . ? C14 C15 1.348(12) . ? C14 H14 0.9500 . ? C15 C16 1.380(9) . ? C15 H15 0.9500 . ? C16 N3 1.357(8) . ? C16 C17 1.464(10) . ? C17 N4 1.360(8) . ? C17 C18 1.380(10) . ? C18 C19 1.369(12) . ? C18 H18 0.9500 . ? C19 C20 1.360(12) . ? C19 H19 0.9500 . ? C20 C21 1.349(10) . ? C20 H20 0.9500 . ? C21 N4 1.330(8) . ? C21 H21 0.9500 . ? N1 Co1 2.102(5) . ? N2 Co1 2.123(5) . ? N3 Co1 2.107(5) . ? N4 Co1 2.122(5) . ? O2 Co1 2.118(4) . ? O2 H2A 0.8601 . ? O2 H2B 0.8619 . ? O3 Co1 2.075(4) . ? O3 H3A 0.8669 . ? O3 H3B 0.8523 . ? Cl1 O6 1.390(5) . ? Cl1 O4 1.391(4) . ? Cl1 O5 1.394(6) . ? Cl1 O7 1.426(6) . ? Cl2 O8 1.380(8) . ? Cl2 O10 1.381(7) . ? Cl2 O9 1.397(9) . ? Cl2 O11 1.428(8) . ? Cl2A O10A 1.385(8) . ? Cl2A O8A 1.387(8) . ? Cl2A O9A 1.404(9) . ? Cl2A O11A 1.420(9) . ? 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 C1 C12 116.2(7) . . ? O1 C1 C2 117.4(7) . . ? C12 C1 C2 126.1(5) . . ? N1 C2 C3 122.5(7) . . ? N1 C2 C1 121.6(6) . . ? C3 C2 C1 115.9(6) . . ? C4 C3 C2 117.7(7) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? C3 C4 C5 121.5(8) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C4 C5 C6 117.8(8) . . ? C4 C5 H5 121.1 . . ? C6 C5 H5 121.1 . . ? N1 C6 C5 121.7(6) . . ? N1 C6 C7 116.3(5) . . ? C5 C6 C7 122.0(7) . . ? N2 C7 C8 122.4(6) . . ? N2 C7 C6 115.2(5) . . ? C8 C7 C6 122.5(6) . . ? C7 C8 C9 118.9(7) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C10 C9 C8 118.5(7) . . ? C10 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? C11 C10 C9 119.3(7) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? N2 C11 C10 123.7(7) . . ? N2 C11 H11 118.2 . . ? C10 C11 H11 118.2 . . ? N3 C12 C13 120.4(7) . . ? N3 C12 C1 121.7(6) . . ? C13 C12 C1 117.8(7) . . ? C14 C13 C12 119.7(8) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C15 C14 C13 119.3(8) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C14 C15 C16 121.0(9) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? N3 C16 C15 120.1(7) . . ? N3 C16 C17 116.9(6) . . ? C15 C16 C17 123.0(8) . . ? N4 C17 C18 120.9(7) . . ? N4 C17 C16 115.1(6) . . ? C18 C17 C16 124.0(7) . . ? C19 C18 C17 119.9(8) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C20 C19 C18 119.5(8) . . ? C20 C19 H19 120.3 . . ? C18 C19 H19 120.3 . . ? C21 C20 C19 117.6(8) . . ? C21 C20 H20 121.2 . . ? C19 C20 H20 121.2 . . ? N4 C21 C20 125.8(8) . . ? N4 C21 H21 117.1 . . ? C20 C21 H21 117.1 . . ? C2 N1 C6 118.6(5) . . ? C2 N1 Co1 126.4(4) . . ? C6 N1 Co1 114.9(4) . . ? C11 N2 C7 117.2(5) . . ? C11 N2 Co1 127.7(5) . . ? C7 N2 Co1 115.1(4) . . ? C12 N3 C16 119.3(6) . . ? C12 N3 Co1 125.7(5) . . ? C16 N3 Co1 114.4(4) . . ? C21 N4 C17 116.3(6) . . ? C21 N4 Co1 128.7(5) . . ? C17 N4 Co1 115.0(4) . . ? Co1 O2 H2A 114.1 . . ? Co1 O2 H2B 134.4 . . ? H2A O2 H2B 105.7 . . ? Co1 O3 H3A 137.1 . . ? Co1 O3 H3B 116.9 . . ? H3A O3 H3B 106.0 . . ? O6 Cl1 O4 111.5(3) . . ? O6 Cl1 O5 109.1(4) . . ? O4 Cl1 O5 111.0(4) . . ? O6 Cl1 O7 112.5(4) . . ? O4 Cl1 O7 108.3(4) . . ? O5 Cl1 O7 104.3(5) . . ? O3 Co1 N1 94.59(17) . . ? O3 Co1 N3 97.31(17) . . ? N1 Co1 N3 91.9(2) . . ? O3 Co1 O2 172.46(17) . . ? N1 Co1 O2 90.13(17) . . ? N3 Co1 O2 88.39(16) . . ? O3 Co1 N4 90.79(18) . . ? N1 Co1 N4 169.0(2) . . ? N3 Co1 N4 77.9(2) . . ? O2 Co1 N4 85.57(18) . . ? O3 Co1 N2 89.15(17) . . ? N1 Co1 N2 78.16(19) . . ? N3 Co1 N2 168.6(2) . . ? O2 Co1 N2 86.06(17) . . ? N4 Co1 N2 111.5(2) . . ? O8 Cl2 O10 111.2(7) . . ? O8 Cl2 O9 109.9(8) . . ? O10 Cl2 O9 109.7(8) . . ? O8 Cl2 O11 109.2(7) . . ? O10 Cl2 O11 111.4(7) . . ? O9 Cl2 O11 105.3(8) . . ? O10A Cl2A O8A 109.5(9) . . ? O10A Cl2A O9A 109.9(9) . . ? O8A Cl2A O9A 109.3(9) . . ? O10A Cl2A O11A 111.5(10) . . ? O8A Cl2A O11A 110.7(9) . . ? O9A Cl2A O11A 105.9(9) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.753 _refine_diff_density_min -0.763 _refine_diff_density_rms 0.173 # Attachment '- 4 Ni aja0607.cif' data_pccn _database_code_depnum_ccdc_archive 'CCDC 774566' #TrackingRef '- 4 Ni aja0607.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic 'bisbipyketone nickel' _chemical_name_common aja0607 _chemical_melting_point ? _chemical_formula_moiety 'C21 H18 N4 Ni O3, 2(Cl O4)' _chemical_formula_sum 'C21 H18 Cl2 N4 Ni O11' _chemical_formula_weight 632.00 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 orthorhombic _symmetry_space_group_name_H-M 'P c c n' _symmetry_space_group_name_Hall '-P 2ab 2ac' _symmetry_int_tables_number 56 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 9.802(2) _cell_length_b 12.453(3) _cell_length_c 19.760(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2412.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8144 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.740 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 1.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7711 _exptl_absorpt_correction_T_max 0.8982 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe electron _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 10140 _diffrn_reflns_av_R_equivalents 0.0909 _diffrn_reflns_av_sigmaI/netI 0.0745 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2755 _reflns_number_gt 2028 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'Dirdiff-99 (Beurskens, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0399P)^2^+1.3889P] 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 2755 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.2500 0.7500 0.01192(2) 0.01586(15) Uani 1 2 d S . . Cl1 Cl -0.02437(7) 0.99844(6) 0.15479(3) 0.02365(19) Uani 1 1 d . . . O1 O 0.1447(2) 0.89770(17) 0.00770(9) 0.0237(5) Uani 1 1 d . . . N1 N 0.3875(2) 0.79921(18) 0.08306(11) 0.0193(5) Uani 1 1 d . . . C1 C 0.2500 0.7500 0.1850(2) 0.0265(9) Uani 1 2 d S . . O2 O 0.2500 0.7500 0.24633(14) 0.0404(9) Uani 1 2 d S . . N2 N 0.3915(2) 0.82292(18) -0.05036(11) 0.0206(5) Uani 1 1 d . . . C2 C 0.3784(3) 0.7878(2) 0.15060(14) 0.0237(6) Uani 1 1 d . . . O3 O 0.1056(2) 0.96793(19) 0.18086(11) 0.0383(6) Uani 1 1 d . . . C3 C 0.4887(3) 0.8113(3) 0.19326(15) 0.0318(8) Uani 1 1 d . . . H3 H 0.4804 0.8035 0.2409 0.038 Uiso 1 1 calc R . . O4 O -0.0176(3) 1.10366(19) 0.12646(12) 0.0467(7) Uani 1 1 d . . . C4 C 0.6089(3) 0.8457(3) 0.16507(17) 0.0372(8) Uani 1 1 d . . . H4 H 0.6848 0.8620 0.1931 0.045 Uiso 1 1 calc R . . O5 O -0.1259(2) 0.9940(2) 0.20638(11) 0.0399(6) Uani 1 1 d . . . C5 C 0.6188(3) 0.8565(3) 0.09669(17) 0.0325(8) Uani 1 1 d . . . H5 H 0.7021 0.8792 0.0767 0.039 Uiso 1 1 calc R . . O6 O -0.0627(2) 0.92382(19) 0.10126(10) 0.0373(6) Uani 1 1 d . . . C6 C 0.5065(3) 0.8340(2) 0.05639(15) 0.0237(7) Uani 1 1 d . . . C7 C 0.5079(3) 0.8492(2) -0.01788(15) 0.0227(6) Uani 1 1 d . . . C8 C 0.6176(3) 0.8927(3) -0.05323(18) 0.0361(8) Uani 1 1 d . . . H8 H 0.6996 0.9106 -0.0302 0.043 Uiso 1 1 calc R . . C9 C 0.6058(4) 0.9096(3) -0.12276(18) 0.0411(9) Uani 1 1 d . . . H9 H 0.6808 0.9366 -0.1480 0.049 Uiso 1 1 calc R . . C10 C 0.4851(4) 0.8869(3) -0.15403(16) 0.0357(8) Uani 1 1 d . . . H10 H 0.4739 0.9005 -0.2010 0.043 Uiso 1 1 calc R . . C11 C 0.3807(3) 0.8444(2) -0.11694(14) 0.0276(7) Uani 1 1 d . . . H11 H 0.2968 0.8293 -0.1391 0.033 Uiso 1 1 calc R . . H1 H 0.0682 0.9017 0.0371 0.073(14) Uiso 1 1 d R . . H2 H 0.1126 0.9034 -0.0376 0.085(15) Uiso 1 1 d 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 Ni1 0.0140(2) 0.0179(3) 0.0157(3) 0.000 0.000 -0.0021(2) Cl1 0.0240(4) 0.0244(4) 0.0225(3) 0.0024(3) -0.0026(3) 0.0012(3) O1 0.0227(11) 0.0241(11) 0.0244(10) 0.0022(9) 0.0002(9) 0.0034(9) N1 0.0214(13) 0.0164(12) 0.0201(11) -0.0020(10) -0.0011(10) 0.0017(10) C1 0.038(2) 0.024(2) 0.018(2) 0.000 0.000 0.012(2) O2 0.048(2) 0.053(2) 0.0203(16) 0.000 0.000 0.0064(17) N2 0.0252(13) 0.0160(12) 0.0208(12) -0.0013(10) 0.0035(10) -0.0031(11) C2 0.0302(17) 0.0205(15) 0.0203(14) -0.0034(12) -0.0015(12) 0.0035(13) O3 0.0220(11) 0.0455(15) 0.0474(14) 0.0123(12) -0.0074(10) 0.0012(11) C3 0.043(2) 0.0275(18) 0.0247(15) -0.0064(13) -0.0117(14) 0.0067(15) O4 0.0640(18) 0.0275(13) 0.0487(14) 0.0124(11) -0.0066(12) 0.0021(13) C4 0.0320(19) 0.035(2) 0.044(2) -0.0054(16) -0.0167(16) -0.0031(16) O5 0.0332(13) 0.0574(16) 0.0291(11) -0.0027(11) 0.0098(10) -0.0013(12) C5 0.0213(17) 0.0275(18) 0.049(2) -0.0052(15) -0.0070(14) -0.0024(14) O6 0.0306(13) 0.0460(15) 0.0353(12) -0.0149(11) 0.0032(10) -0.0071(12) C6 0.0156(15) 0.0212(16) 0.0341(16) -0.0029(13) -0.0033(12) -0.0017(12) C7 0.0173(14) 0.0174(15) 0.0335(16) -0.0049(13) 0.0055(12) -0.0036(12) C8 0.0227(17) 0.0336(19) 0.052(2) -0.0064(16) 0.0095(15) -0.0067(15) C9 0.041(2) 0.034(2) 0.048(2) 0.0053(17) 0.0243(17) -0.0081(17) C10 0.051(2) 0.0266(18) 0.0291(16) 0.0030(14) 0.0136(15) -0.0064(16) C11 0.0407(19) 0.0202(16) 0.0220(15) 0.0002(12) 0.0074(13) -0.0045(14) _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 N1 2.042(2) . ? Ni1 N1 2.042(2) 2_565 ? Ni1 N2 2.064(2) 2_565 ? Ni1 N2 2.064(2) . ? Ni1 O1 2.111(2) 2_565 ? Ni1 O1 2.111(2) . ? Cl1 O5 1.425(2) . ? Cl1 O3 1.426(2) . ? Cl1 O4 1.426(2) . ? Cl1 O6 1.457(2) . ? O1 H1 0.9499 . ? O1 H2 0.9516 . ? N1 C2 1.345(3) . ? N1 C6 1.351(4) . ? C1 O2 1.212(5) . ? C1 C2 1.506(3) 2_565 ? C1 C2 1.506(3) . ? N2 C11 1.347(3) . ? N2 C7 1.350(4) . ? C2 C3 1.402(4) . ? C3 C4 1.372(5) . ? C3 H3 0.9500 . ? C4 C5 1.361(5) . ? C4 H4 0.9500 . ? C5 C6 1.387(4) . ? C5 H5 0.9500 . ? C6 C7 1.480(4) . ? C7 C8 1.391(4) . ? C8 C9 1.395(5) . ? C8 H8 0.9500 . ? C9 C10 1.364(5) . ? C9 H9 0.9500 . ? C10 C11 1.366(4) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? 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 N1 Ni1 N1 92.97(13) . 2_565 ? N1 Ni1 N2 170.37(9) . 2_565 ? N1 Ni1 N2 80.51(9) 2_565 2_565 ? N1 Ni1 N2 80.51(9) . . ? N1 Ni1 N2 170.37(9) 2_565 . ? N2 Ni1 N2 106.81(13) 2_565 . ? N1 Ni1 O1 88.05(8) . 2_565 ? N1 Ni1 O1 95.07(8) 2_565 2_565 ? N2 Ni1 O1 85.50(9) 2_565 2_565 ? N2 Ni1 O1 91.80(9) . 2_565 ? N1 Ni1 O1 95.07(8) . . ? N1 Ni1 O1 88.05(8) 2_565 . ? N2 Ni1 O1 91.80(9) 2_565 . ? N2 Ni1 O1 85.50(9) . . ? O1 Ni1 O1 175.47(10) 2_565 . ? O5 Cl1 O3 110.81(14) . . ? O5 Cl1 O4 110.39(15) . . ? O3 Cl1 O4 110.17(15) . . ? O5 Cl1 O6 108.35(14) . . ? O3 Cl1 O6 108.81(14) . . ? O4 Cl1 O6 108.24(14) . . ? Ni1 O1 H1 114.0 . . ? Ni1 O1 H2 105.3 . . ? H1 O1 H2 108.1 . . ? C2 N1 C6 118.6(2) . . ? C2 N1 Ni1 127.42(19) . . ? C6 N1 Ni1 113.42(18) . . ? O2 C1 C2 116.81(17) . 2_565 ? O2 C1 C2 116.81(17) . . ? C2 C1 C2 126.4(3) 2_565 . ? C11 N2 C7 118.8(2) . . ? C11 N2 Ni1 128.1(2) . . ? C7 N2 Ni1 113.03(18) . . ? N1 C2 C3 121.6(3) . . ? N1 C2 C1 122.4(3) . . ? C3 C2 C1 116.0(3) . . ? C4 C3 C2 118.9(3) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C5 C4 C3 119.7(3) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 119.5(3) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? N1 C6 C5 121.7(3) . . ? N1 C6 C7 115.8(2) . . ? C5 C6 C7 122.4(3) . . ? N2 C7 C8 120.6(3) . . ? N2 C7 C6 115.6(2) . . ? C8 C7 C6 123.7(3) . . ? C7 C8 C9 119.3(3) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C10 C9 C8 119.1(3) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C9 C10 C11 119.1(3) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? N2 C11 C10 122.9(3) . . ? N2 C11 H11 118.6 . . ? C10 C11 H11 118.6 . . ? 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 N1 Ni1 N1 C2 4.93(19) 2_565 . . . ? O1 Ni1 N1 C2 -90.0(2) 2_565 . . . ? O1 Ni1 N1 C2 93.2(2) . . . . ? N1 Ni1 N1 C6 175.9(2) 2_565 . . . ? N2 Ni1 N1 C6 -11.2(2) . . . . ? O1 Ni1 N1 C6 80.9(2) 2_565 . . . ? O1 Ni1 N1 C6 -95.8(2) . . . . ? N1 Ni1 N2 C11 -171.0(2) . . . . ? N2 Ni1 N2 C11 15.4(2) 2_565 . . . ? O1 Ni1 N2 C11 101.2(2) 2_565 . . . ? O1 Ni1 N2 C11 -75.1(2) . . . . ? N1 Ni1 N2 C7 10.00(19) . . . . ? N2 Ni1 N2 C7 -163.6(2) 2_565 . . . ? O1 Ni1 N2 C7 -77.7(2) 2_565 . . . ? O1 Ni1 N2 C7 105.9(2) . . . . ? C6 N1 C2 C3 0.1(4) . . . . ? Ni1 N1 C2 C3 170.7(2) . . . . ? C6 N1 C2 C1 179.8(2) . . . . ? Ni1 N1 C2 C1 -9.7(4) . . . . ? O2 C1 C2 N1 -174.89(19) . . . . ? C2 C1 C2 N1 5.11(19) 2_565 . . . ? O2 C1 C2 C3 4.8(3) . . . . ? C2 C1 C2 C3 -175.2(3) 2_565 . . . ? N1 C2 C3 C4 -0.6(4) . . . . ? C1 C2 C3 C4 179.7(3) . . . . ? C2 C3 C4 C5 0.0(5) . . . . ? C3 C4 C5 C6 1.0(5) . . . . ? C2 N1 C6 C5 1.0(4) . . . . ? Ni1 N1 C6 C5 -170.9(2) . . . . ? C2 N1 C6 C7 -177.5(2) . . . . ? Ni1 N1 C6 C7 10.7(3) . . . . ? C4 C5 C6 N1 -1.5(5) . . . . ? C4 C5 C6 C7 176.8(3) . . . . ? C11 N2 C7 C8 -3.3(4) . . . . ? Ni1 N2 C7 C8 175.8(2) . . . . ? C11 N2 C7 C6 173.6(2) . . . . ? Ni1 N2 C7 C6 -7.3(3) . . . . ? N1 C6 C7 N2 -2.2(4) . . . . ? C5 C6 C7 N2 179.4(3) . . . . ? N1 C6 C7 C8 174.6(3) . . . . ? C5 C6 C7 C8 -3.8(5) . . . . ? N2 C7 C8 C9 0.4(5) . . . . ? C6 C7 C8 C9 -176.2(3) . . . . ? C7 C8 C9 C10 2.5(5) . . . . ? C8 C9 C10 C11 -2.5(5) . . . . ? C7 N2 C11 C10 3.3(4) . . . . ? Ni1 N2 C11 C10 -175.6(2) . . . . ? C9 C10 C11 N2 -0.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.380 _refine_diff_density_min -0.512 _refine_diff_density_rms 0.091 _chemical_compound_source 'synthesised by authors' _exptl_crystal_recrystallization_method 'slow diffusion of ether in acetonitrile' # Attachment '- 5 Cu aja0504.cif' data_aja0504 _database_code_depnum_ccdc_archive 'CCDC 774567' #TrackingRef '- 5 Cu aja0504.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H14 Cl2 Cu N4 O9' _chemical_formula_sum 'C21 H14 Cl2 Cu N4 O9' _chemical_formula_weight 600.80 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' 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4710(3) _cell_length_b 9.9530(3) _cell_length_c 12.4610(5) _cell_angle_alpha 71.2520(10) _cell_angle_beta 80.9860(10) _cell_angle_gamma 78.4190(10) _cell_volume 1084.28(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11332 _cell_measurement_theta_min 3.57 _cell_measurement_theta_max 26.37 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.840 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 606 _exptl_absorpt_coefficient_mu 1.320 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7782 _exptl_absorpt_correction_T_max 0.9017 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker-Nonius KappaCCD' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 15393 _diffrn_reflns_av_R_equivalents 0.0859 _diffrn_reflns_av_sigmaI/netI 0.0795 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4419 _reflns_number_gt 3345 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0394P)^2^+0.9526P] 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 4419 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0739 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1101 _refine_ls_wR_factor_gt 0.0992 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 C21 C 0.8134(4) 0.7617(4) -0.0184(3) 0.0212(8) Uani 1 1 d . . . H1 H 0.7148 0.7550 -0.0186 0.025 Uiso 1 1 calc R . . C20 C 0.9068(4) 0.7590(4) -0.1146(3) 0.0247(9) Uani 1 1 d . . . H2 H 0.8734 0.7495 -0.1794 0.030 Uiso 1 1 calc R . . C19 C 1.0508(4) 0.7704(4) -0.1149(3) 0.0282(9) Uani 1 1 d . . . H3 H 1.1184 0.7647 -0.1788 0.034 Uiso 1 1 calc R . . C18 C 1.0938(4) 0.7901(4) -0.0216(3) 0.0255(9) Uani 1 1 d . . . H4 H 1.1907 0.8022 -0.0217 0.031 Uiso 1 1 calc R . . C17 C 0.9951(4) 0.7921(4) 0.0727(3) 0.0178(8) Uani 1 1 d . . . C16 C 1.0257(4) 0.8237(4) 0.1747(3) 0.0189(8) Uani 1 1 d . . . C15 C 1.1562(4) 0.8596(4) 0.1850(3) 0.0226(8) Uani 1 1 d . . . H7 H 1.2354 0.8581 0.1280 0.027 Uiso 1 1 calc R . . C14 C 1.1681(4) 0.8977(4) 0.2801(3) 0.0244(9) Uani 1 1 d . . . H8 H 1.2565 0.9218 0.2894 0.029 Uiso 1 1 calc R . . C13 C 1.0519(4) 0.9005(4) 0.3613(3) 0.0233(8) Uani 1 1 d . . . H9 H 1.0588 0.9279 0.4264 0.028 Uiso 1 1 calc R . . C12 C 0.9244(4) 0.8629(4) 0.3467(3) 0.0190(8) Uani 1 1 d . . . C1 C 0.7956(4) 0.8806(4) 0.4317(3) 0.0197(8) Uani 1 1 d . . . C2 C 0.6605(4) 0.8143(4) 0.4479(3) 0.0179(8) Uani 1 1 d . . . C3 C 0.5620(4) 0.8261(4) 0.5400(3) 0.0201(8) Uani 1 1 d . . . H13 H 0.5822 0.8706 0.5916 0.024 Uiso 1 1 calc R . . C4 C 0.4336(4) 0.7725(4) 0.5565(3) 0.0239(8) Uani 1 1 d . . . H14 H 0.3639 0.7814 0.6186 0.029 Uiso 1 1 calc R . . C5 C 0.4082(4) 0.7057(4) 0.4811(3) 0.0199(8) Uani 1 1 d . . . H15 H 0.3212 0.6676 0.4912 0.024 Uiso 1 1 calc R . . C6 C 0.5108(4) 0.6952(4) 0.3915(3) 0.0178(8) Uani 1 1 d . . . C7 C 0.4973(4) 0.6206(4) 0.3085(3) 0.0169(8) Uani 1 1 d . . . C8 C 0.3788(4) 0.5550(4) 0.3126(3) 0.0206(8) Uani 1 1 d . . . H18 H 0.2974 0.5615 0.3669 0.025 Uiso 1 1 calc R . . C9 C 0.3829(4) 0.4804(4) 0.2355(3) 0.0254(9) Uani 1 1 d . . . H19 H 0.3020 0.4382 0.2341 0.030 Uiso 1 1 calc R . . C10 C 0.5050(4) 0.4675(4) 0.1606(3) 0.0247(9) Uani 1 1 d . . . H20 H 0.5114 0.4119 0.1102 0.030 Uiso 1 1 calc R . . C11 C 0.6173(4) 0.5365(4) 0.1604(3) 0.0208(8) Uani 1 1 d . . . H21 H 0.7014 0.5276 0.1088 0.025 Uiso 1 1 calc R . . N2 N 0.6125(3) 0.6158(3) 0.2301(3) 0.0185(7) Uani 1 1 d . . . N1 N 0.6359(3) 0.7497(3) 0.3739(3) 0.0165(6) Uani 1 1 d . . . N3 N 0.9130(3) 0.8222(3) 0.2561(3) 0.0166(6) Uani 1 1 d . . . N4 N 0.8561(3) 0.7734(3) 0.0751(3) 0.0176(7) Uani 1 1 d . . . O1 O 0.8000(3) 0.9552(3) 0.4911(2) 0.0259(6) Uani 1 1 d . . . O2 O 0.4038(3) 1.1251(3) 0.2141(2) 0.0330(7) Uani 1 1 d . . . O3 O 0.5563(3) 1.1859(3) 0.0442(2) 0.0268(6) Uani 1 1 d . . . O4 O 0.6561(3) 1.0847(3) 0.2203(2) 0.0268(6) Uani 1 1 d . . . O5 O 0.5489(3) 0.9420(3) 0.1473(3) 0.0369(7) Uani 1 1 d . . . O6 O 0.8637(3) 0.4787(3) 0.4322(3) 0.0413(8) Uani 1 1 d . . . O7 O 1.1003(3) 0.3699(3) 0.3872(3) 0.0382(8) Uani 1 1 d . . . O8 O 0.9011(3) 0.2812(3) 0.3613(2) 0.0345(7) Uani 1 1 d . . . O9 O 0.9551(3) 0.5051(3) 0.2417(3) 0.0426(8) Uani 1 1 d . . . Cu1 Cu 0.75205(4) 0.74145(5) 0.23034(4) 0.01796(14) Uani 1 1 d . . . Cl2 Cl 0.95565(9) 0.40810(9) 0.35613(8) 0.0223(2) Uani 1 1 d . . . Cl1 Cl 0.54165(9) 1.08457(9) 0.15629(8) 0.0191(2) 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 C21 0.0207(19) 0.022(2) 0.022(2) -0.0072(16) -0.0029(16) -0.0049(16) C20 0.026(2) 0.028(2) 0.022(2) -0.0113(17) 0.0008(16) -0.0055(17) C19 0.023(2) 0.036(2) 0.025(2) -0.0112(18) 0.0084(17) -0.0092(18) C18 0.018(2) 0.029(2) 0.030(2) -0.0086(18) -0.0005(16) -0.0063(16) C17 0.0147(18) 0.0165(18) 0.021(2) -0.0030(15) -0.0018(15) -0.0036(14) C16 0.0184(19) 0.0132(18) 0.022(2) -0.0003(15) -0.0038(15) -0.0021(14) C15 0.0157(19) 0.023(2) 0.026(2) -0.0041(17) 0.0000(16) -0.0049(15) C14 0.020(2) 0.021(2) 0.033(2) -0.0038(17) -0.0073(17) -0.0070(16) C13 0.026(2) 0.023(2) 0.026(2) -0.0076(17) -0.0075(17) -0.0093(16) C12 0.0221(19) 0.0136(18) 0.021(2) -0.0025(15) -0.0055(15) -0.0037(15) C1 0.0201(19) 0.0203(19) 0.020(2) -0.0078(16) -0.0044(15) -0.0021(15) C2 0.0193(19) 0.0148(18) 0.019(2) -0.0031(15) -0.0033(15) -0.0026(15) C3 0.025(2) 0.0164(19) 0.019(2) -0.0064(15) -0.0047(16) -0.0016(15) C4 0.023(2) 0.024(2) 0.020(2) -0.0055(17) 0.0015(16) 0.0017(16) C5 0.0203(19) 0.0204(19) 0.019(2) -0.0043(16) -0.0025(15) -0.0046(15) C6 0.0166(18) 0.0154(18) 0.020(2) -0.0024(15) -0.0008(15) -0.0042(14) C7 0.0187(18) 0.0144(18) 0.017(2) -0.0032(15) -0.0024(15) -0.0035(14) C8 0.0174(19) 0.024(2) 0.021(2) -0.0084(17) 0.0008(15) -0.0044(16) C9 0.025(2) 0.024(2) 0.029(2) -0.0060(17) -0.0050(17) -0.0108(17) C10 0.033(2) 0.020(2) 0.025(2) -0.0095(17) -0.0041(17) -0.0082(17) C11 0.025(2) 0.023(2) 0.016(2) -0.0093(16) 0.0024(15) -0.0057(16) N2 0.0183(16) 0.0169(16) 0.0213(18) -0.0066(13) -0.0027(13) -0.0032(12) N1 0.0160(15) 0.0147(15) 0.0211(18) -0.0068(13) -0.0035(12) -0.0040(12) N3 0.0137(15) 0.0154(15) 0.0208(17) -0.0051(13) -0.0013(12) -0.0032(12) N4 0.0128(15) 0.0189(16) 0.0207(17) -0.0041(13) -0.0028(12) -0.0040(12) O1 0.0279(15) 0.0270(15) 0.0293(16) -0.0165(13) -0.0018(12) -0.0064(12) O2 0.0171(14) 0.0518(19) 0.0317(18) -0.0170(14) 0.0041(12) -0.0069(13) O3 0.0236(14) 0.0282(15) 0.0253(16) -0.0007(12) -0.0015(12) -0.0095(12) O4 0.0235(14) 0.0338(16) 0.0250(16) -0.0058(12) -0.0083(12) -0.0093(12) O5 0.056(2) 0.0222(15) 0.0370(19) -0.0125(13) -0.0184(15) -0.0011(13) O6 0.0284(16) 0.0468(18) 0.059(2) -0.0369(17) 0.0157(15) -0.0094(14) O7 0.0231(15) 0.0417(18) 0.044(2) -0.0041(15) -0.0089(13) -0.0026(13) O8 0.0430(18) 0.0291(16) 0.0368(18) -0.0140(14) 0.0073(14) -0.0195(13) O9 0.053(2) 0.0313(17) 0.0349(19) 0.0066(14) -0.0090(15) -0.0109(15) Cu1 0.0156(2) 0.0223(3) 0.0192(3) -0.00907(19) 0.00122(17) -0.00769(18) Cl2 0.0199(5) 0.0218(5) 0.0251(5) -0.0064(4) -0.0006(4) -0.0050(4) Cl1 0.0176(4) 0.0198(5) 0.0205(5) -0.0058(4) -0.0021(4) -0.0044(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 C21 N4 1.338(5) . ? C21 C20 1.377(5) . ? C21 H1 0.9500 . ? C20 C19 1.390(5) . ? C20 H2 0.9500 . ? C19 C18 1.372(5) . ? C19 H3 0.9500 . ? C18 C17 1.385(5) . ? C18 H4 0.9500 . ? C17 N4 1.360(4) . ? C17 C16 1.485(5) . ? C16 N3 1.352(4) . ? C16 C15 1.389(5) . ? C15 C14 1.381(5) . ? C15 H7 0.9500 . ? C14 C13 1.376(5) . ? C14 H8 0.9500 . ? C13 C12 1.387(5) . ? C13 H9 0.9500 . ? C12 N3 1.341(4) . ? C12 C1 1.507(5) . ? C1 O1 1.215(4) . ? C1 C2 1.512(5) . ? C2 N1 1.352(4) . ? C2 C3 1.382(5) . ? C3 C4 1.385(5) . ? C3 H13 0.9500 . ? C4 C5 1.385(5) . ? C4 H14 0.9500 . ? C5 C6 1.377(5) . ? C5 H15 0.9500 . ? C6 N1 1.359(4) . ? C6 C7 1.487(5) . ? C7 N2 1.350(4) . ? C7 C8 1.393(5) . ? C8 C9 1.382(5) . ? C8 H18 0.9500 . ? C9 C10 1.380(5) . ? C9 H19 0.9500 . ? C10 C11 1.377(5) . ? C10 H20 0.9500 . ? C11 N2 1.339(4) . ? C11 H21 0.9500 . ? N2 Cu1 1.995(3) . ? N1 Cu1 1.964(3) . ? N3 Cu1 1.971(3) . ? N4 Cu1 1.987(3) . ? O2 Cl1 1.437(3) . ? O3 Cl1 1.441(3) . ? O4 Cl1 1.443(2) . ? O5 Cl1 1.446(3) . ? O5 Cu1 2.552(3) . ? O6 Cl2 1.440(3) . ? O6 Cu1 3.127(3) . ? O7 Cl2 1.426(3) . ? O8 Cl2 1.437(3) . ? O9 Cl2 1.443(3) . ? O9 Cu1 2.703(3) . ? 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 C21 C20 122.6(3) . . ? N4 C21 H1 118.7 . . ? C20 C21 H1 118.7 . . ? C21 C20 C19 118.7(4) . . ? C21 C20 H2 120.6 . . ? C19 C20 H2 120.6 . . ? C18 C19 C20 119.1(4) . . ? C18 C19 H3 120.5 . . ? C20 C19 H3 120.5 . . ? C19 C18 C17 119.7(3) . . ? C19 C18 H4 120.2 . . ? C17 C18 H4 120.2 . . ? N4 C17 C18 121.1(3) . . ? N4 C17 C16 114.2(3) . . ? C18 C17 C16 124.5(3) . . ? N3 C16 C15 121.6(3) . . ? N3 C16 C17 114.7(3) . . ? C15 C16 C17 123.7(3) . . ? C14 C15 C16 118.4(4) . . ? C14 C15 H7 120.8 . . ? C16 C15 H7 120.8 . . ? C13 C14 C15 120.0(3) . . ? C13 C14 H8 120.0 . . ? C15 C14 H8 120.0 . . ? C14 C13 C12 119.1(3) . . ? C14 C13 H9 120.5 . . ? C12 C13 H9 120.5 . . ? N3 C12 C13 121.4(3) . . ? N3 C12 C1 121.1(3) . . ? C13 C12 C1 117.3(3) . . ? O1 C1 C12 117.5(3) . . ? O1 C1 C2 117.5(3) . . ? C12 C1 C2 125.1(3) . . ? N1 C2 C3 121.7(3) . . ? N1 C2 C1 121.4(3) . . ? C3 C2 C1 116.9(3) . . ? C2 C3 C4 119.5(3) . . ? C2 C3 H13 120.3 . . ? C4 C3 H13 120.3 . . ? C3 C4 C5 119.0(4) . . ? C3 C4 H14 120.5 . . ? C5 C4 H14 120.5 . . ? C6 C5 C4 119.2(3) . . ? C6 C5 H15 120.4 . . ? C4 C5 H15 120.4 . . ? N1 C6 C5 122.0(3) . . ? N1 C6 C7 114.4(3) . . ? C5 C6 C7 123.6(3) . . ? N2 C7 C8 121.8(3) . . ? N2 C7 C6 114.6(3) . . ? C8 C7 C6 123.6(3) . . ? C9 C8 C7 118.3(3) . . ? C9 C8 H18 120.8 . . ? C7 C8 H18 120.8 . . ? C10 C9 C8 119.7(3) . . ? C10 C9 H19 120.1 . . ? C8 C9 H19 120.1 . . ? C11 C10 C9 118.8(3) . . ? C11 C10 H20 120.6 . . ? C9 C10 H20 120.6 . . ? N2 C11 C10 122.4(3) . . ? N2 C11 H21 118.8 . . ? C10 C11 H21 118.8 . . ? C11 N2 C7 118.7(3) . . ? C11 N2 Cu1 128.3(2) . . ? C7 N2 Cu1 112.9(2) . . ? C2 N1 C6 118.6(3) . . ? C2 N1 Cu1 127.2(2) . . ? C6 N1 Cu1 113.8(2) . . ? C12 N3 C16 119.5(3) . . ? C12 N3 Cu1 127.3(2) . . ? C16 N3 Cu1 113.0(2) . . ? C21 N4 C17 118.6(3) . . ? C21 N4 Cu1 128.8(2) . . ? C17 N4 Cu1 112.0(2) . . ? Cl1 O5 Cu1 120.09(15) . . ? Cl2 O6 Cu1 92.35(15) . . ? Cl2 O9 Cu1 111.28(17) . . ? N1 Cu1 N3 95.14(12) . . ? N1 Cu1 N4 169.00(11) . . ? N3 Cu1 N4 82.46(12) . . ? N1 Cu1 N2 82.48(12) . . ? N3 Cu1 N2 165.99(12) . . ? N4 Cu1 N2 102.38(12) . . ? N1 Cu1 O5 81.78(11) . . ? N3 Cu1 O5 110.56(10) . . ? N4 Cu1 O5 88.99(11) . . ? N2 Cu1 O5 82.86(10) . . ? N1 Cu1 O9 116.14(10) . . ? N3 Cu1 O9 83.53(10) . . ? N4 Cu1 O9 74.38(10) . . ? N2 Cu1 O9 85.14(10) . . ? O5 Cu1 O9 156.88(9) . . ? N1 Cu1 O6 69.60(10) . . ? N3 Cu1 O6 83.27(10) . . ? N4 Cu1 O6 120.51(10) . . ? N2 Cu1 O6 82.97(10) . . ? O5 Cu1 O6 149.43(9) . . ? O9 Cu1 O6 46.74(8) . . ? O7 Cl2 O8 109.77(17) . . ? O7 Cl2 O6 110.25(19) . . ? O8 Cl2 O6 109.30(16) . . ? O7 Cl2 O9 109.11(17) . . ? O8 Cl2 O9 109.53(18) . . ? O6 Cl2 O9 108.87(19) . . ? O2 Cl1 O3 109.17(16) . . ? O2 Cl1 O4 109.43(16) . . ? O3 Cl1 O4 109.79(15) . . ? O2 Cl1 O5 109.04(17) . . ? O3 Cl1 O5 109.82(17) . . ? O4 Cl1 O5 109.58(16) . . ? 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 N4 C21 C20 C19 -0.7(6) . . . . ? C21 C20 C19 C18 -2.7(6) . . . . ? C20 C19 C18 C17 2.7(6) . . . . ? C19 C18 C17 N4 0.7(5) . . . . ? C19 C18 C17 C16 -175.0(3) . . . . ? N4 C17 C16 N3 3.0(4) . . . . ? C18 C17 C16 N3 179.0(3) . . . . ? N4 C17 C16 C15 -173.7(3) . . . . ? C18 C17 C16 C15 2.2(6) . . . . ? N3 C16 C15 C14 -1.5(5) . . . . ? C17 C16 C15 C14 175.0(3) . . . . ? C16 C15 C14 C13 -0.6(5) . . . . ? C15 C14 C13 C12 0.9(6) . . . . ? C14 C13 C12 N3 0.9(5) . . . . ? C14 C13 C12 C1 -174.5(3) . . . . ? N3 C12 C1 O1 -159.2(3) . . . . ? C13 C12 C1 O1 16.2(5) . . . . ? N3 C12 C1 C2 20.0(5) . . . . ? C13 C12 C1 C2 -164.6(3) . . . . ? O1 C1 C2 N1 169.1(3) . . . . ? C12 C1 C2 N1 -10.1(5) . . . . ? O1 C1 C2 C3 -9.3(5) . . . . ? C12 C1 C2 C3 171.5(3) . . . . ? N1 C2 C3 C4 -1.0(5) . . . . ? C1 C2 C3 C4 177.4(3) . . . . ? C2 C3 C4 C5 1.2(5) . . . . ? C3 C4 C5 C6 -0.4(5) . . . . ? C4 C5 C6 N1 -0.6(5) . . . . ? C4 C5 C6 C7 177.4(3) . . . . ? N1 C6 C7 N2 1.3(4) . . . . ? C5 C6 C7 N2 -176.9(3) . . . . ? N1 C6 C7 C8 178.8(3) . . . . ? C5 C6 C7 C8 0.7(6) . . . . ? N2 C7 C8 C9 1.7(5) . . . . ? C6 C7 C8 C9 -175.6(3) . . . . ? C7 C8 C9 C10 2.8(6) . . . . ? C8 C9 C10 C11 -3.6(6) . . . . ? C9 C10 C11 N2 0.0(6) . . . . ? C10 C11 N2 C7 4.4(5) . . . . ? C10 C11 N2 Cu1 -172.2(3) . . . . ? C8 C7 N2 C11 -5.2(5) . . . . ? C6 C7 N2 C11 172.3(3) . . . . ? C8 C7 N2 Cu1 171.8(3) . . . . ? C6 C7 N2 Cu1 -10.6(4) . . . . ? C3 C2 N1 C6 -0.1(5) . . . . ? C1 C2 N1 C6 -178.4(3) . . . . ? C3 C2 N1 Cu1 172.8(3) . . . . ? C1 C2 N1 Cu1 -5.5(5) . . . . ? C5 C6 N1 C2 0.9(5) . . . . ? C7 C6 N1 C2 -177.3(3) . . . . ? C5 C6 N1 Cu1 -172.9(3) . . . . ? C7 C6 N1 Cu1 8.8(4) . . . . ? C13 C12 N3 C16 -2.9(5) . . . . ? C1 C12 N3 C16 172.3(3) . . . . ? C13 C12 N3 Cu1 171.4(3) . . . . ? C1 C12 N3 Cu1 -13.4(5) . . . . ? C15 C16 N3 C12 3.3(5) . . . . ? C17 C16 N3 C12 -173.6(3) . . . . ? C15 C16 N3 Cu1 -171.9(3) . . . . ? C17 C16 N3 Cu1 11.3(4) . . . . ? C20 C21 N4 C17 4.1(5) . . . . ? C20 C21 N4 Cu1 -166.8(3) . . . . ? C18 C17 N4 C21 -4.0(5) . . . . ? C16 C17 N4 C21 172.1(3) . . . . ? C18 C17 N4 Cu1 168.3(3) . . . . ? C16 C17 N4 Cu1 -15.6(4) . . . . ? C2 N1 Cu1 N3 9.2(3) . . . . ? C6 N1 Cu1 N3 -177.6(2) . . . . ? C2 N1 Cu1 N4 -67.6(7) . . . . ? C6 N1 Cu1 N4 105.6(6) . . . . ? C2 N1 Cu1 N2 175.3(3) . . . . ? C6 N1 Cu1 N2 -11.5(2) . . . . ? C2 N1 Cu1 O5 -100.9(3) . . . . ? C6 N1 Cu1 O5 72.4(2) . . . . ? C2 N1 Cu1 O9 94.5(3) . . . . ? C6 N1 Cu1 O9 -92.3(2) . . . . ? C2 N1 Cu1 O6 90.1(3) . . . . ? C6 N1 Cu1 O6 -96.7(2) . . . . ? C12 N3 Cu1 N1 0.5(3) . . . . ? C16 N3 Cu1 N1 175.2(2) . . . . ? C12 N3 Cu1 N4 169.7(3) . . . . ? C16 N3 Cu1 N4 -15.6(2) . . . . ? C12 N3 Cu1 N2 -79.0(6) . . . . ? C16 N3 Cu1 N2 95.7(5) . . . . ? C12 N3 Cu1 O5 83.7(3) . . . . ? C16 N3 Cu1 O5 -101.7(2) . . . . ? C12 N3 Cu1 O9 -115.2(3) . . . . ? C16 N3 Cu1 O9 59.4(2) . . . . ? C12 N3 Cu1 O6 -68.2(3) . . . . ? C16 N3 Cu1 O6 106.5(2) . . . . ? C21 N4 Cu1 N1 -93.5(6) . . . . ? C17 N4 Cu1 N1 95.2(6) . . . . ? C21 N4 Cu1 N3 -171.5(3) . . . . ? C17 N4 Cu1 N3 17.2(2) . . . . ? C21 N4 Cu1 N2 21.8(3) . . . . ? C17 N4 Cu1 N2 -149.5(2) . . . . ? C21 N4 Cu1 O5 -60.6(3) . . . . ? C17 N4 Cu1 O5 128.1(2) . . . . ? C21 N4 Cu1 O9 103.1(3) . . . . ? C17 N4 Cu1 O9 -68.2(2) . . . . ? C21 N4 Cu1 O6 110.9(3) . . . . ? C17 N4 Cu1 O6 -60.4(3) . . . . ? C11 N2 Cu1 N1 -171.1(3) . . . . ? C7 N2 Cu1 N1 12.2(2) . . . . ? C11 N2 Cu1 N3 -90.1(6) . . . . ? C7 N2 Cu1 N3 93.2(5) . . . . ? C11 N2 Cu1 N4 18.9(3) . . . . ? C7 N2 Cu1 N4 -157.8(2) . . . . ? C11 N2 Cu1 O5 106.3(3) . . . . ? C7 N2 Cu1 O5 -70.4(2) . . . . ? C11 N2 Cu1 O9 -53.9(3) . . . . ? C7 N2 Cu1 O9 129.4(2) . . . . ? C11 N2 Cu1 O6 -100.9(3) . . . . ? C7 N2 Cu1 O6 82.4(2) . . . . ? Cl1 O5 Cu1 N1 74.4(2) . . . . ? Cl1 O5 Cu1 N3 -18.0(2) . . . . ? Cl1 O5 Cu1 N4 -99.6(2) . . . . ? Cl1 O5 Cu1 N2 157.8(2) . . . . ? Cl1 O5 Cu1 O9 -142.94(19) . . . . ? Cl1 O5 Cu1 O6 94.8(2) . . . . ? Cl2 O9 Cu1 N1 -0.2(2) . . . . ? Cl2 O9 Cu1 N3 92.39(18) . . . . ? Cl2 O9 Cu1 N4 176.34(19) . . . . ? Cl2 O9 Cu1 N2 -79.35(18) . . . . ? Cl2 O9 Cu1 O5 -138.2(2) . . . . ? Cl2 O9 Cu1 O6 5.56(12) . . . . ? Cl2 O6 Cu1 N1 169.30(15) . . . . ? Cl2 O6 Cu1 N3 -92.64(14) . . . . ? Cl2 O6 Cu1 N4 -15.52(17) . . . . ? Cl2 O6 Cu1 N2 84.74(14) . . . . ? Cl2 O6 Cu1 O5 147.67(13) . . . . ? Cl2 O6 Cu1 O9 -5.20(11) . . . . ? Cu1 O6 Cl2 O7 127.16(14) . . . . ? Cu1 O6 Cl2 O8 -112.09(15) . . . . ? Cu1 O6 Cl2 O9 7.51(16) . . . . ? Cu1 O9 Cl2 O7 -129.69(16) . . . . ? Cu1 O9 Cl2 O8 110.13(17) . . . . ? Cu1 O9 Cl2 O6 -9.3(2) . . . . ? Cu1 O5 Cl1 O2 -122.58(18) . . . . ? Cu1 O5 Cl1 O3 117.85(17) . . . . ? Cu1 O5 Cl1 O4 -2.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.426 _refine_diff_density_min -0.544 _refine_diff_density_rms 0.105 # Attachment '- 6 Zn aja0722.cif' data_aja0722 _database_code_depnum_ccdc_archive 'CCDC 774568' #TrackingRef '- 6 Zn aja0722.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common aja0723 _chemical_melting_point ? _chemical_formula_moiety 'C21 H18 N4 O3 Zn, 2(Cl O4)' _chemical_formula_sum 'C21 H18 Cl2 N4 O11 Zn' _chemical_formula_weight 638.66 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 orthorhombic _symmetry_space_group_name_H-M Pccn _symmetry_space_group_name_Hall '-P 2ab 2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 9.8506(3) _cell_length_b 12.4696(4) _cell_length_c 19.7856(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2430.33(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8577 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.745 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 1.301 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.524 _exptl_absorpt_correction_T_max 0.552 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8971 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2758 _reflns_number_gt 2229 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0356P)^2^+2.6986P] 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 2758 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.0956 _refine_ls_wR_factor_gt 0.0895 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 C1 C 0.7500 0.2500 0.1880(2) 0.0216(8) Uani 1 2 d S . . C2 C 0.6204(3) 0.2872(2) 0.15395(13) 0.0192(5) Uani 1 1 d . . . C3 C 0.5123(3) 0.3094(2) 0.19696(15) 0.0267(6) Uani 1 1 d . . . H3 H 0.5217 0.3009 0.2444 0.032 Uiso 1 1 calc R . . C4 C 0.3911(3) 0.3440(2) 0.16940(17) 0.0328(7) Uani 1 1 d . . . H4 H 0.3157 0.3593 0.1977 0.039 Uiso 1 1 calc R . . C5 C 0.3811(3) 0.3561(2) 0.10024(16) 0.0284(7) Uani 1 1 d . . . H5 H 0.2982 0.3793 0.0805 0.034 Uiso 1 1 calc R . . C6 C 0.4925(2) 0.3342(2) 0.05979(14) 0.0199(6) Uani 1 1 d . . . C7 C 0.4900(3) 0.3505(2) -0.01498(14) 0.0197(6) Uani 1 1 d . . . C8 C 0.3782(3) 0.3927(2) -0.04872(17) 0.0326(7) Uani 1 1 d . . . H8 H 0.2972 0.4091 -0.0248 0.039 Uiso 1 1 calc R . . C9 C 0.3871(4) 0.4105(2) -0.11805(17) 0.0393(8) Uani 1 1 d . . . H9 H 0.3113 0.4379 -0.1423 0.047 Uiso 1 1 calc R . . C10 C 0.5058(3) 0.3882(2) -0.15098(16) 0.0352(8) Uani 1 1 d . . . H10 H 0.5146 0.4017 -0.1980 0.042 Uiso 1 1 calc R . . C11 C 0.6128(3) 0.3458(2) -0.11453(14) 0.0249(6) Uani 1 1 d . . . H11 H 0.6952 0.3301 -0.1374 0.030 Uiso 1 1 calc R . . N1 N 0.6110(2) 0.29901(16) 0.08664(11) 0.0159(4) Uani 1 1 d . . . N2 N 0.6046(2) 0.32584(16) -0.04829(11) 0.0185(5) Uani 1 1 d . . . O1 O 0.7500 0.2500 0.24951(14) 0.0343(7) Uani 1 2 d S . . O2 O 0.63929(19) 0.09754(15) 0.00689(9) 0.0229(4) Uani 1 1 d . . . H2A H 0.5905 0.0963 -0.0344 0.027 Uiso 1 1 d . . . H2B H 0.5681 0.0940 0.0369 0.027 Uiso 1 1 d . . . O3 O 0.4370(2) 0.07742(17) 0.10332(10) 0.0322(5) Uani 1 1 d . . . O4 O 0.3718(2) 0.00601(18) 0.20809(10) 0.0355(5) Uani 1 1 d . . . O5 O 0.6025(2) 0.03187(17) 0.18397(11) 0.0348(5) Uani 1 1 d . . . O6 O 0.4809(3) -0.10345(16) 0.12834(11) 0.0402(6) Uani 1 1 d . . . Cl1 Cl 0.47353(7) 0.00230(5) 0.15695(3) 0.02093(16) Uani 1 1 d . . . Zn1 Zn 0.7500 0.2500 0.01177(2) 0.01521(13) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.028(2) 0.0177(17) 0.019(2) 0.000 0.000 -0.0068(17) C2 0.0232(13) 0.0150(11) 0.0195(13) -0.0029(10) 0.0035(11) -0.0031(11) C3 0.0309(15) 0.0234(14) 0.0256(15) -0.0055(11) 0.0091(12) -0.0023(13) C4 0.0257(15) 0.0290(15) 0.0437(19) -0.0097(14) 0.0162(14) -0.0008(13) C5 0.0171(13) 0.0231(14) 0.0448(19) -0.0043(13) 0.0047(13) 0.0026(12) C6 0.0147(12) 0.0165(12) 0.0286(15) -0.0045(11) 0.0016(11) 0.0012(10) C7 0.0165(12) 0.0148(12) 0.0279(15) -0.0032(10) -0.0050(11) 0.0034(10) C8 0.0212(14) 0.0313(15) 0.045(2) -0.0006(14) -0.0089(14) 0.0084(13) C9 0.0420(19) 0.0311(16) 0.045(2) 0.0008(15) -0.0250(16) 0.0109(15) C10 0.052(2) 0.0244(15) 0.0292(17) 0.0025(13) -0.0160(15) 0.0042(15) C11 0.0342(16) 0.0200(13) 0.0205(14) 0.0005(11) -0.0047(12) 0.0028(12) N1 0.0138(10) 0.0150(10) 0.0190(11) -0.0027(8) 0.0011(9) -0.0012(9) N2 0.0199(11) 0.0175(10) 0.0180(12) -0.0010(9) -0.0025(9) 0.0019(9) O1 0.0418(18) 0.0450(18) 0.0160(16) 0.000 0.000 -0.0014(15) O2 0.0238(10) 0.0222(9) 0.0227(10) -0.0041(8) 0.0010(8) -0.0038(8) O3 0.0238(11) 0.0392(12) 0.0335(12) 0.0141(9) 0.0028(9) 0.0052(10) O4 0.0298(11) 0.0506(13) 0.0260(11) 0.0032(10) 0.0083(9) 0.0021(10) O5 0.0222(10) 0.0418(12) 0.0404(13) -0.0097(10) -0.0091(10) 0.0014(10) O6 0.0603(16) 0.0211(10) 0.0393(13) -0.0111(9) -0.0048(11) 0.0002(11) Cl1 0.0212(3) 0.0214(3) 0.0202(3) -0.0021(3) -0.0015(3) -0.0005(3) Zn1 0.0138(2) 0.0178(2) 0.0140(2) 0.000 0.000 0.00343(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 C1 O1 1.216(4) . ? C1 C2 1.517(3) . ? C1 C2 1.517(3) 2_655 ? C2 N1 1.343(3) . ? C2 C3 1.391(4) . ? C3 C4 1.381(4) . ? C3 H3 0.9500 . ? C4 C5 1.380(4) . ? C4 H4 0.9500 . ? C5 C6 1.385(4) . ? C5 H5 0.9500 . ? C6 N1 1.356(3) . ? C6 C7 1.494(4) . ? C7 N2 1.344(3) . ? C7 C8 1.391(4) . ? C8 C9 1.392(5) . ? C8 H8 0.9500 . ? C9 C10 1.367(5) . ? C9 H9 0.9500 . ? C10 C11 1.383(4) . ? C10 H10 0.9500 . ? C11 N2 1.336(3) . ? C11 H11 0.9500 . ? N1 Zn1 2.108(2) . ? N2 Zn1 2.087(2) . ? O2 Zn1 2.1938(18) . ? O2 H2A 0.9479 . ? O2 H2B 0.9200 . ? O3 Cl1 1.460(2) . ? O4 Cl1 1.425(2) . ? O5 Cl1 1.427(2) . ? O6 Cl1 1.437(2) . ? Zn1 N2 2.087(2) 2_655 ? Zn1 N1 2.108(2) 2_655 ? Zn1 O2 2.1938(18) 2_655 ? 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 C1 C2 116.39(17) . . ? O1 C1 C2 116.39(17) . 2_655 ? C2 C1 C2 127.2(3) . 2_655 ? N1 C2 C3 122.2(3) . . ? N1 C2 C1 122.2(2) . . ? C3 C2 C1 115.7(3) . . ? C4 C3 C2 118.8(3) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C5 C4 C3 119.2(3) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 119.6(3) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? N1 C6 C5 121.3(3) . . ? N1 C6 C7 116.5(2) . . ? C5 C6 C7 122.2(2) . . ? N2 C7 C8 121.1(3) . . ? N2 C7 C6 116.1(2) . . ? C8 C7 C6 122.7(2) . . ? C7 C8 C9 118.9(3) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C10 C9 C8 119.4(3) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 118.8(3) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? N2 C11 C10 122.5(3) . . ? N2 C11 H11 118.8 . . ? C10 C11 H11 118.8 . . ? C2 N1 C6 118.9(2) . . ? C2 N1 Zn1 128.36(17) . . ? C6 N1 Zn1 112.20(17) . . ? C11 N2 C7 119.3(2) . . ? C11 N2 Zn1 126.95(18) . . ? C7 N2 Zn1 113.66(17) . . ? Zn1 O2 H2A 107.7 . . ? Zn1 O2 H2B 113.1 . . ? H2A O2 H2B 99.7 . . ? O4 Cl1 O5 110.58(13) . . ? O4 Cl1 O6 110.20(14) . . ? O5 Cl1 O6 109.86(14) . . ? O4 Cl1 O3 108.77(13) . . ? O5 Cl1 O3 109.03(13) . . ? O6 Cl1 O3 108.36(13) . . ? N2 Zn1 N2 110.60(12) . 2_655 ? N2 Zn1 N1 167.72(8) . 2_655 ? N2 Zn1 N1 79.81(8) 2_655 2_655 ? N2 Zn1 N1 79.81(8) . . ? N2 Zn1 N1 167.72(8) 2_655 . ? N1 Zn1 N1 90.69(12) 2_655 . ? N2 Zn1 O2 85.60(8) . 2_655 ? N2 Zn1 O2 91.52(8) 2_655 2_655 ? N1 Zn1 O2 87.67(7) 2_655 2_655 ? N1 Zn1 O2 95.89(7) . 2_655 ? N2 Zn1 O2 91.52(8) . . ? N2 Zn1 O2 85.60(8) 2_655 . ? N1 Zn1 O2 95.89(7) 2_655 . ? N1 Zn1 O2 87.67(7) . . ? O2 Zn1 O2 174.95(10) 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 O1 C1 C2 N1 174.62(17) . . . . ? C2 C1 C2 N1 -5.38(17) 2_655 . . . ? O1 C1 C2 C3 -4.7(2) . . . . ? C2 C1 C2 C3 175.3(2) 2_655 . . . ? N1 C2 C3 C4 0.4(4) . . . . ? C1 C2 C3 C4 179.8(2) . . . . ? C2 C3 C4 C5 -0.3(4) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? C4 C5 C6 N1 1.3(4) . . . . ? C4 C5 C6 C7 -177.1(2) . . . . ? N1 C6 C7 N2 1.7(3) . . . . ? C5 C6 C7 N2 -179.8(2) . . . . ? N1 C6 C7 C8 -175.8(2) . . . . ? C5 C6 C7 C8 2.7(4) . . . . ? N2 C7 C8 C9 -0.8(4) . . . . ? C6 C7 C8 C9 176.7(3) . . . . ? C7 C8 C9 C10 -1.3(4) . . . . ? C8 C9 C10 C11 1.7(5) . . . . ? C9 C10 C11 N2 -0.1(4) . . . . ? C3 C2 N1 C6 0.3(4) . . . . ? C1 C2 N1 C6 -179.0(2) . . . . ? C3 C2 N1 Zn1 -170.47(19) . . . . ? C1 C2 N1 Zn1 10.2(3) . . . . ? C5 C6 N1 C2 -1.2(4) . . . . ? C7 C6 N1 C2 177.3(2) . . . . ? C5 C6 N1 Zn1 171.0(2) . . . . ? C7 C6 N1 Zn1 -10.5(3) . . . . ? C10 C11 N2 C7 -1.9(4) . . . . ? C10 C11 N2 Zn1 174.2(2) . . . . ? C8 C7 N2 C11 2.4(4) . . . . ? C6 C7 N2 C11 -175.2(2) . . . . ? C8 C7 N2 Zn1 -174.3(2) . . . . ? C6 C7 N2 Zn1 8.1(3) . . . . ? C11 N2 Zn1 N2 -13.62(18) . . . 2_655 ? C7 N2 Zn1 N2 162.7(2) . . . 2_655 ? C11 N2 Zn1 N1 133.3(4) . . . 2_655 ? C7 N2 Zn1 N1 -50.4(5) . . . 2_655 ? C11 N2 Zn1 N1 173.1(2) . . . . ? C7 N2 Zn1 N1 -10.53(17) . . . . ? C11 N2 Zn1 O2 76.4(2) . . . 2_655 ? C7 N2 Zn1 O2 -107.32(18) . . . 2_655 ? C11 N2 Zn1 O2 -99.5(2) . . . . ? C7 N2 Zn1 O2 76.83(18) . . . . ? C2 N1 Zn1 N2 -177.4(2) . . . . ? C6 N1 Zn1 N2 11.28(17) . . . . ? C2 N1 Zn1 N2 33.8(5) . . . 2_655 ? C6 N1 Zn1 N2 -137.5(4) . . . 2_655 ? C2 N1 Zn1 N1 -5.26(16) . . . 2_655 ? C6 N1 Zn1 N1 -176.6(2) . . . 2_655 ? C2 N1 Zn1 O2 -93.0(2) . . . 2_655 ? C6 N1 Zn1 O2 95.72(17) . . . 2_655 ? C2 N1 Zn1 O2 90.6(2) . . . . ? C6 N1 Zn1 O2 -80.69(17) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.329 _refine_diff_density_min -0.482 _refine_diff_density_rms 0.083 # Attachment '7-Zn-hemiketal.cif' data_shelxl_Zn7 _database_code_depnum_ccdc_archive 'CCDC 774569' #TrackingRef '7-Zn-hemiketal.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H34 N8 O4 Zn2, 2(Cl O4)' _chemical_formula_sum 'C44 H34 Cl2 N8 O12 Zn2' _chemical_formula_weight 1068.43 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' Zn Zn 0.2839 1.4301 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 9.515(2) _cell_length_b 15.661(3) _cell_length_c 15.612(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.87(3) _cell_angle_gamma 90.00 _cell_volume 2258.6(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 17542 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.571 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 1.253 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8343 _exptl_absorpt_correction_T_max 0.8849 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker-Nonius KappaCCD' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17542 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 24.95 _reflns_number_total 3967 _reflns_number_gt 3967 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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. Restraints were applied to the anisotropic displacement parameters of oxygen atoms O4, O7 and O24 ; _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^)+(0.0496P)^2^+5.0551P] 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 4291 _refine_ls_number_parameters 308 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1220 _refine_ls_wR_factor_gt 0.1212 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.103 _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 C1 C 0.3926(3) 0.1208(2) 0.6617(2) 0.0294(6) Uani 1 1 d . . . H1 H 0.3967 0.0665 0.6893 0.035 Uiso 1 1 calc R . . C2 C 0.5133(3) 0.1742(2) 0.6841(2) 0.0335(7) Uani 1 1 d . . . H2 H 0.5982 0.1569 0.7262 0.040 Uiso 1 1 calc R . . C3 C 0.5054(3) 0.2527(2) 0.6433(2) 0.0349(7) Uani 1 1 d . . . H3 H 0.5847 0.2911 0.6581 0.042 Uiso 1 1 calc R . . C4 C 0.3822(3) 0.27538(19) 0.5809(2) 0.0285(6) Uani 1 1 d . . . H4 H 0.3768 0.3287 0.5513 0.034 Uiso 1 1 calc R . . C5 C 0.2661(3) 0.21879(18) 0.56193(19) 0.0229(6) Uani 1 1 d . . . C6 C 0.1285(3) 0.23794(17) 0.49691(18) 0.0213(5) Uani 1 1 d . . . C7 C 0.0960(3) 0.31480(18) 0.4521(2) 0.0260(6) Uani 1 1 d . . . H7 H 0.1656 0.3594 0.4596 0.031 Uiso 1 1 calc R . . C8 C -0.0396(4) 0.32505(19) 0.3963(2) 0.0293(6) Uani 1 1 d . . . H8 H -0.0650 0.3778 0.3665 0.035 Uiso 1 1 calc R . . C9 C -0.1385(3) 0.2585(2) 0.3836(2) 0.0279(6) Uani 1 1 d . . . H9 H -0.2320 0.2648 0.3454 0.034 Uiso 1 1 calc R . . C10 C -0.0973(3) 0.18245(18) 0.42822(18) 0.0214(5) Uani 1 1 d . . . C11 C -0.1922(3) 0.10089(19) 0.41615(19) 0.0223(6) Uani 1 1 d . . . C12 C -0.0791(3) 0.2243(2) 0.6666(2) 0.0277(6) Uani 1 1 d . . . H12 H -0.1021 0.2512 0.6104 0.033 Uiso 1 1 calc R . . C13 C -0.1197(3) 0.2651(2) 0.7370(2) 0.0321(7) Uani 1 1 d . . . H13 H -0.1665 0.3191 0.7293 0.038 Uiso 1 1 calc R . . C14 C -0.0896(3) 0.2243(2) 0.8177(2) 0.0341(7) Uani 1 1 d . . . H14 H -0.1189 0.2492 0.8662 0.041 Uiso 1 1 calc R . . C15 C -0.0168(4) 0.1475(2) 0.8277(2) 0.0324(7) Uani 1 1 d . . . H15 H 0.0051 0.1189 0.8830 0.039 Uiso 1 1 calc R . . C16 C 0.0243(3) 0.1121(2) 0.75479(19) 0.0257(6) Uani 1 1 d . . . C17 C 0.1123(3) 0.0336(2) 0.76003(18) 0.0256(6) Uani 1 1 d . . . C18 C 0.1971(4) 0.0012(2) 0.8388(2) 0.0314(7) Uani 1 1 d . . . H18 H 0.1920 0.0248 0.8940 0.038 Uiso 1 1 calc R . . C19 C 0.2878(4) -0.0654(2) 0.8344(2) 0.0340(7) Uani 1 1 d . . . H19 H 0.3490 -0.0872 0.8871 0.041 Uiso 1 1 calc R . . C20 C 0.2914(3) -0.1020(2) 0.7533(2) 0.0300(7) Uani 1 1 d . . . H20 H 0.3537 -0.1486 0.7500 0.036 Uiso 1 1 calc R . . C21 C 0.2002(3) -0.06777(18) 0.67736(19) 0.0232(6) Uani 1 1 d . . . C22 C -0.3628(4) 0.1561(2) 0.4898(2) 0.0373(7) Uani 1 1 d . . . H22A H -0.3053 0.1248 0.5406 0.056 Uiso 1 1 calc R . . H22B H -0.4658 0.1511 0.4890 0.056 Uiso 1 1 calc R . . H22C H -0.3347 0.2165 0.4944 0.056 Uiso 1 1 calc R . . N1 N 0.2716(3) 0.14303(15) 0.60303(16) 0.0238(5) Uani 1 1 d . . . N2 N 0.0312(2) 0.17392(15) 0.48381(15) 0.0196(5) Uani 1 1 d . . . N3 N -0.0098(3) 0.14961(16) 0.67473(16) 0.0246(5) Uani 1 1 d . . . N4 N 0.1159(2) -0.00152(15) 0.68182(15) 0.0217(5) Uani 1 1 d . . . Zn1 Zn 0.06056(3) 0.07162(2) 0.56856(2) 0.01974(15) Uani 1 1 d . . . Cl1 Cl 0.73870(9) 0.46644(5) 0.59813(5) 0.0314(2) Uani 1 1 d . . . O1 O -0.3384(2) 0.12224(15) 0.41288(15) 0.0317(5) Uani 1 1 d . . . O2 O -0.1354(2) 0.04110(12) 0.47906(12) 0.0199(4) Uani 1 1 d . . . O3 O 0.6450(3) 0.44397(16) 0.65455(18) 0.0419(6) Uani 1 1 d . . . O4 O 0.7597(5) 0.3928(2) 0.5490(2) 0.0798(12) Uani 1 1 d U . . O5 O 0.8722(3) 0.4990(2) 0.6522(2) 0.0668(10) Uani 1 1 d . . . O6 O 0.6718(3) 0.53173(14) 0.53761(15) 0.0314(5) 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 C1 0.0234(14) 0.0256(14) 0.0351(16) 0.0037(12) -0.0011(12) -0.0054(12) C2 0.0207(14) 0.0322(16) 0.0431(18) 0.0007(14) -0.0015(13) -0.0051(12) C3 0.0248(15) 0.0264(15) 0.051(2) -0.0028(14) 0.0039(14) -0.0097(12) C4 0.0242(14) 0.0187(13) 0.0425(17) -0.0009(12) 0.0075(12) -0.0037(11) C5 0.0218(13) 0.0186(13) 0.0288(14) -0.0009(11) 0.0070(11) -0.0020(10) C6 0.0229(13) 0.0183(13) 0.0237(13) -0.0009(10) 0.0077(11) -0.0022(10) C7 0.0317(15) 0.0181(13) 0.0290(14) 0.0002(11) 0.0091(12) -0.0023(11) C8 0.0377(17) 0.0194(14) 0.0292(15) 0.0048(11) 0.0047(12) 0.0032(12) C9 0.0270(15) 0.0261(15) 0.0283(15) 0.0038(12) 0.0017(12) 0.0033(12) C10 0.0203(12) 0.0219(13) 0.0219(13) 0.0019(10) 0.0048(10) 0.0010(10) C11 0.0159(12) 0.0244(14) 0.0243(14) 0.0063(11) 0.0006(10) -0.0010(10) C12 0.0239(14) 0.0288(15) 0.0273(14) -0.0063(12) 0.0001(11) -0.0033(11) C13 0.0224(14) 0.0356(17) 0.0358(17) -0.0123(13) 0.0021(12) -0.0052(12) C14 0.0274(15) 0.0424(18) 0.0341(16) -0.0137(14) 0.0104(13) -0.0097(13) C15 0.0308(16) 0.0426(18) 0.0239(14) -0.0035(13) 0.0065(12) -0.0129(14) C16 0.0223(13) 0.0310(15) 0.0225(13) -0.0022(11) 0.0028(11) -0.0107(11) C17 0.0253(14) 0.0309(15) 0.0192(13) 0.0020(11) 0.0026(11) -0.0118(12) C18 0.0371(16) 0.0335(16) 0.0209(14) 0.0049(12) 0.0016(12) -0.0085(13) C19 0.0370(17) 0.0357(17) 0.0228(15) 0.0101(12) -0.0055(13) -0.0104(13) C20 0.0264(15) 0.0286(15) 0.0298(15) 0.0100(12) -0.0032(12) -0.0028(12) C21 0.0189(13) 0.0246(14) 0.0231(14) 0.0058(11) -0.0010(11) -0.0080(10) C22 0.0309(16) 0.0404(19) 0.0386(18) 0.0003(14) 0.0048(14) 0.0019(14) N1 0.0203(11) 0.0213(12) 0.0278(12) 0.0024(9) 0.0018(9) -0.0041(9) N2 0.0196(11) 0.0186(11) 0.0208(11) 0.0011(9) 0.0050(9) -0.0006(9) N3 0.0215(11) 0.0281(13) 0.0222(12) -0.0039(10) 0.0016(9) -0.0066(9) N4 0.0193(11) 0.0228(12) 0.0213(11) 0.0039(9) 0.0013(9) -0.0066(9) Zn1 0.0177(2) 0.0200(2) 0.0190(2) 0.00420(11) -0.00069(12) -0.00414(11) Cl1 0.0389(4) 0.0225(4) 0.0350(4) 0.0048(3) 0.0132(3) 0.0026(3) O1 0.0182(10) 0.0402(13) 0.0364(12) 0.0088(10) 0.0059(9) 0.0049(9) O2 0.0165(9) 0.0207(9) 0.0202(9) 0.0044(7) -0.0002(7) -0.0022(7) O3 0.0497(15) 0.0355(13) 0.0436(14) 0.0094(11) 0.0176(12) -0.0058(11) O4 0.147(4) 0.0373(16) 0.069(2) 0.0041(15) 0.054(2) 0.032(2) O5 0.0349(14) 0.084(2) 0.072(2) 0.0391(18) -0.0068(14) -0.0083(15) O6 0.0367(12) 0.0271(11) 0.0296(11) 0.0038(9) 0.0063(9) -0.0023(9) _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 C1 N1 1.334(4) . ? C1 C2 1.395(4) . ? C1 H1 0.9500 . ? C2 C3 1.379(5) . ? C2 H2 0.9500 . ? C3 C4 1.379(5) . ? C3 H3 0.9500 . ? C4 C5 1.392(4) . ? C4 H4 0.9500 . ? C5 N1 1.344(4) . ? C5 C6 1.482(4) . ? C6 N2 1.347(4) . ? C6 C7 1.390(4) . ? C7 C8 1.382(5) . ? C7 H7 0.9500 . ? C8 C9 1.386(4) . ? C8 H8 0.9500 . ? C9 C10 1.388(4) . ? C9 H9 0.9500 . ? C10 N2 1.325(4) . ? C10 C11 1.549(4) . ? C11 O2 1.371(3) . ? C11 C21 1.534(4) 3_556 ? C12 N3 1.334(4) . ? C12 C13 1.402(4) . ? C12 H12 0.9500 . ? C13 C14 1.380(5) . ? C13 H13 0.9500 . ? C14 C15 1.379(5) . ? C14 H14 0.9500 . ? C15 C16 1.404(4) . ? C15 H15 0.9500 . ? C16 N3 1.348(4) . ? C16 C17 1.479(5) . ? C17 N4 1.347(4) . ? C17 C18 1.394(4) . ? C18 C19 1.366(5) . ? C18 H18 0.9500 . ? C19 C20 1.397(5) . ? C19 H19 0.9500 . ? C20 C21 1.397(4) . ? C20 H20 0.9500 . ? C21 N4 1.323(4) . ? C21 C11 1.534(4) 3_556 ? C22 O1 1.382(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? N1 Zn1 2.248(2) . ? N2 Zn1 2.054(2) . ? N3 Zn1 2.285(3) . ? N4 Zn1 2.066(2) . ? Zn1 O2 2.099(2) . ? Zn1 O2 2.105(2) 3_556 ? Zn1 Zn1 3.1241(8) 3_556 ? Cl1 O4 1.426(3) . ? Cl1 O6 1.434(2) . ? Cl1 O5 1.439(3) . ? Cl1 O3 1.439(3) . ? O2 Zn1 2.105(2) 3_556 ? 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 N1 C1 C2 122.7(3) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C3 C2 C1 117.9(3) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 118.9(3) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? N1 C5 C4 121.5(3) . . ? N1 C5 C6 115.6(2) . . ? C4 C5 C6 122.9(3) . . ? N2 C6 C7 120.4(3) . . ? N2 C6 C5 114.6(2) . . ? C7 C6 C5 125.0(3) . . ? C8 C7 C6 118.6(3) . . ? C8 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? C7 C8 C9 120.1(3) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C10 118.2(3) . . ? C8 C9 H9 120.9 . . ? C10 C9 H9 120.9 . . ? N2 C10 C9 121.3(3) . . ? N2 C10 C11 114.6(2) . . ? C9 C10 C11 124.1(3) . . ? O2 C11 C21 111.8(2) . 3_556 ? O2 C11 C10 111.0(2) . . ? C21 C11 C10 106.8(2) 3_556 . ? N3 C12 C13 123.1(3) . . ? N3 C12 H12 118.4 . . ? C13 C12 H12 118.4 . . ? C14 C13 C12 118.0(3) . . ? C14 C13 H13 121.0 . . ? C12 C13 H13 121.0 . . ? C15 C14 C13 119.7(3) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 118.9(3) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? N3 C16 C15 121.9(3) . . ? N3 C16 C17 114.9(3) . . ? C15 C16 C17 123.2(3) . . ? N4 C17 C18 121.1(3) . . ? N4 C17 C16 115.2(3) . . ? C18 C17 C16 123.5(3) . . ? C19 C18 C17 118.2(3) . . ? C19 C18 H18 120.9 . . ? C17 C18 H18 120.9 . . ? C18 C19 C20 120.7(3) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C21 C20 C19 117.9(3) . . ? C21 C20 H20 121.1 . . ? C19 C20 H20 121.1 . . ? N4 C21 C20 121.1(3) . . ? N4 C21 C11 115.0(2) . 3_556 ? C20 C21 C11 123.9(3) . 3_556 ? O1 C22 H22A 109.5 . . ? O1 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O1 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C1 N1 C5 119.1(3) . . ? C1 N1 Zn1 127.5(2) . . ? C5 N1 Zn1 113.24(19) . . ? C10 N2 C6 121.1(2) . . ? C10 N2 Zn1 117.52(18) . . ? C6 N2 Zn1 120.02(19) . . ? C12 N3 C16 118.3(3) . . ? C12 N3 Zn1 128.6(2) . . ? C16 N3 Zn1 113.1(2) . . ? C21 N4 C17 121.0(3) . . ? C21 N4 Zn1 115.02(19) . . ? C17 N4 Zn1 119.5(2) . . ? N2 Zn1 N4 162.01(9) . . ? N2 Zn1 O2 77.69(8) . . ? N4 Zn1 O2 116.55(8) . . ? N2 Zn1 O2 115.60(8) . 3_556 ? N4 Zn1 O2 78.40(9) . 3_556 ? O2 Zn1 O2 84.00(8) . 3_556 ? N2 Zn1 N1 75.05(9) . . ? N4 Zn1 N1 92.35(9) . . ? O2 Zn1 N1 150.72(8) . . ? O2 Zn1 N1 98.25(8) 3_556 . ? N2 Zn1 N3 91.84(9) . . ? N4 Zn1 N3 74.59(10) . . ? O2 Zn1 N3 103.69(8) . . ? O2 Zn1 N3 152.55(8) 3_556 . ? N1 Zn1 N3 87.74(9) . . ? N2 Zn1 Zn1 98.50(7) . 3_556 ? N4 Zn1 Zn1 99.49(7) . 3_556 ? O2 Zn1 Zn1 42.07(6) . 3_556 ? O2 Zn1 Zn1 41.94(5) 3_556 3_556 ? N1 Zn1 Zn1 133.07(7) . 3_556 ? N3 Zn1 Zn1 139.19(6) . 3_556 ? O4 Cl1 O6 108.64(19) . . ? O4 Cl1 O5 112.6(3) . . ? O6 Cl1 O5 108.93(17) . . ? O4 Cl1 O3 108.6(2) . . ? O6 Cl1 O3 109.60(15) . . ? O5 Cl1 O3 108.45(19) . . ? C11 O2 Zn1 117.13(16) . . ? C11 O2 Zn1 115.37(17) . 3_556 ? Zn1 O2 Zn1 96.00(8) . 3_556 ? 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 N1 C1 C2 C3 -0.1(5) . . . . ? C1 C2 C3 C4 -1.6(5) . . . . ? C2 C3 C4 C5 1.6(5) . . . . ? C3 C4 C5 N1 0.1(5) . . . . ? C3 C4 C5 C6 179.1(3) . . . . ? N1 C5 C6 N2 -4.2(4) . . . . ? C4 C5 C6 N2 176.7(3) . . . . ? N1 C5 C6 C7 175.0(3) . . . . ? C4 C5 C6 C7 -4.1(5) . . . . ? N2 C6 C7 C8 2.2(4) . . . . ? C5 C6 C7 C8 -177.0(3) . . . . ? C6 C7 C8 C9 -2.1(5) . . . . ? C7 C8 C9 C10 0.0(5) . . . . ? C8 C9 C10 N2 2.2(4) . . . . ? C8 C9 C10 C11 -175.9(3) . . . . ? N2 C10 C11 O2 12.2(3) . . . . ? C9 C10 C11 O2 -169.6(3) . . . . ? N2 C10 C11 C21 -109.9(3) . . . 3_556 ? C9 C10 C11 C21 68.3(3) . . . 3_556 ? N3 C12 C13 C14 -1.8(5) . . . . ? C12 C13 C14 C15 2.4(4) . . . . ? C13 C14 C15 C16 -0.4(5) . . . . ? C14 C15 C16 N3 -2.4(4) . . . . ? C14 C15 C16 C17 175.2(3) . . . . ? N3 C16 C17 N4 -15.9(4) . . . . ? C15 C16 C17 N4 166.4(3) . . . . ? N3 C16 C17 C18 158.4(3) . . . . ? C15 C16 C17 C18 -19.3(4) . . . . ? N4 C17 C18 C19 2.1(4) . . . . ? C16 C17 C18 C19 -171.9(3) . . . . ? C17 C18 C19 C20 -2.2(5) . . . . ? C18 C19 C20 C21 0.4(5) . . . . ? C19 C20 C21 N4 1.7(4) . . . . ? C19 C20 C21 C11 179.9(3) . . . 3_556 ? C2 C1 N1 C5 1.7(5) . . . . ? C2 C1 N1 Zn1 -173.6(3) . . . . ? C4 C5 N1 C1 -1.7(4) . . . . ? C6 C5 N1 C1 179.2(3) . . . . ? C4 C5 N1 Zn1 174.2(2) . . . . ? C6 C5 N1 Zn1 -4.9(3) . . . . ? C9 C10 N2 C6 -2.2(4) . . . . ? C11 C10 N2 C6 176.1(2) . . . . ? C9 C10 N2 Zn1 164.8(2) . . . . ? C11 C10 N2 Zn1 -17.0(3) . . . . ? C7 C6 N2 C10 0.0(4) . . . . ? C5 C6 N2 C10 179.2(2) . . . . ? C7 C6 N2 Zn1 -166.7(2) . . . . ? C5 C6 N2 Zn1 12.6(3) . . . . ? C13 C12 N3 C16 -0.8(4) . . . . ? C13 C12 N3 Zn1 178.4(2) . . . . ? C15 C16 N3 C12 3.0(4) . . . . ? C17 C16 N3 C12 -174.8(2) . . . . ? C15 C16 N3 Zn1 -176.4(2) . . . . ? C17 C16 N3 Zn1 5.9(3) . . . . ? C20 C21 N4 C17 -1.9(4) . . . . ? C11 C21 N4 C17 179.7(2) 3_556 . . . ? C20 C21 N4 Zn1 154.4(2) . . . . ? C11 C21 N4 Zn1 -24.0(3) 3_556 . . . ? C18 C17 N4 C21 -0.1(4) . . . . ? C16 C17 N4 C21 174.4(2) . . . . ? C18 C17 N4 Zn1 -155.2(2) . . . . ? C16 C17 N4 Zn1 19.2(3) . . . . ? C10 N2 Zn1 N4 -131.8(3) . . . . ? C6 N2 Zn1 N4 35.3(4) . . . . ? C10 N2 Zn1 O2 12.2(2) . . . . ? C6 N2 Zn1 O2 179.3(2) . . . . ? C10 N2 Zn1 O2 89.3(2) . . . 3_556 ? C6 N2 Zn1 O2 -103.6(2) . . . 3_556 ? C10 N2 Zn1 N1 -178.6(2) . . . . ? C6 N2 Zn1 N1 -11.5(2) . . . . ? C10 N2 Zn1 N3 -91.4(2) . . . . ? C6 N2 Zn1 N3 75.7(2) . . . . ? C10 N2 Zn1 Zn1 49.0(2) . . . 3_556 ? C6 N2 Zn1 Zn1 -143.90(19) . . . 3_556 ? C21 N4 Zn1 N2 -126.4(3) . . . . ? C17 N4 Zn1 N2 30.2(4) . . . . ? C21 N4 Zn1 O2 93.5(2) . . . . ? C17 N4 Zn1 O2 -109.9(2) . . . . ? C21 N4 Zn1 O2 16.36(18) . . . 3_556 ? C17 N4 Zn1 O2 173.0(2) . . . 3_556 ? C21 N4 Zn1 N1 -81.6(2) . . . . ? C17 N4 Zn1 N1 75.0(2) . . . . ? C21 N4 Zn1 N3 -168.6(2) . . . . ? C17 N4 Zn1 N3 -12.0(2) . . . . ? C21 N4 Zn1 Zn1 52.82(19) . . . 3_556 ? C17 N4 Zn1 Zn1 -150.58(19) . . . 3_556 ? C1 N1 Zn1 N2 -176.0(3) . . . . ? C5 N1 Zn1 N2 8.42(19) . . . . ? C1 N1 Zn1 N4 17.0(3) . . . . ? C5 N1 Zn1 N4 -158.6(2) . . . . ? C1 N1 Zn1 O2 -154.1(2) . . . . ? C5 N1 Zn1 O2 30.4(3) . . . . ? C1 N1 Zn1 O2 -61.6(3) . . . 3_556 ? C5 N1 Zn1 O2 122.8(2) . . . 3_556 ? C1 N1 Zn1 N3 91.5(3) . . . . ? C5 N1 Zn1 N3 -84.1(2) . . . . ? C1 N1 Zn1 Zn1 -88.3(3) . . . 3_556 ? C5 N1 Zn1 Zn1 96.1(2) . . . 3_556 ? C12 N3 Zn1 N2 15.3(2) . . . . ? C16 N3 Zn1 N2 -165.43(19) . . . . ? C12 N3 Zn1 N4 -176.7(3) . . . . ? C16 N3 Zn1 N4 2.59(18) . . . . ? C12 N3 Zn1 O2 -62.4(2) . . . . ? C16 N3 Zn1 O2 116.80(19) . . . . ? C12 N3 Zn1 O2 -166.1(2) . . . 3_556 ? C16 N3 Zn1 O2 13.2(3) . . . 3_556 ? C12 N3 Zn1 N1 90.3(2) . . . . ? C16 N3 Zn1 N1 -90.5(2) . . . . ? C12 N3 Zn1 Zn1 -89.9(3) . . . 3_556 ? C16 N3 Zn1 Zn1 89.3(2) . . . 3_556 ? C21 C11 O2 Zn1 117.0(2) 3_556 . . . ? C10 C11 O2 Zn1 -2.2(3) . . . . ? C21 C11 O2 Zn1 5.1(3) 3_556 . . 3_556 ? C10 C11 O2 Zn1 -114.1(2) . . . 3_556 ? N2 Zn1 O2 C11 -4.66(19) . . . . ? N4 Zn1 O2 C11 163.63(19) . . . . ? O2 Zn1 O2 C11 -122.5(2) 3_556 . . . ? N1 Zn1 O2 C11 -26.4(3) . . . . ? N3 Zn1 O2 C11 84.2(2) . . . . ? Zn1 Zn1 O2 C11 -122.5(2) 3_556 . . . ? N2 Zn1 O2 Zn1 117.88(9) . . . 3_556 ? N4 Zn1 O2 Zn1 -73.83(11) . . . 3_556 ? O2 Zn1 O2 Zn1 0.0 3_556 . . 3_556 ? N1 Zn1 O2 Zn1 96.19(17) . . . 3_556 ? N3 Zn1 O2 Zn1 -153.23(8) . . . 3_556 ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 24.95 _diffrn_measured_fraction_theta_full 0.931 _refine_diff_density_max 0.779 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.073 # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.500 0.500 10.6 1.5 2 0.221 0.559 0.136 58.8 -3.5 3 0.279 0.059 0.364 57.7 -3.3 4 0.500 0.000 0.000 10.6 1.5 5 0.725 -0.059 0.638 57.9 -3.4 6 0.775 0.441 0.862 56.8 -3.2 _platon_squeeze_details ; ; # start Validation Reply Form _vrf_PLAT029_shelxl ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.93 RESPONSE: As a result of squeezing the structure, this value reduced 0.999 to 0.931. ; # end Validation Reply Form # end Validation Reply Form # Attachment '- 8 Cd aja0702.cif' data_aja0702 _database_code_depnum_ccdc_archive 'CCDC 774570' #TrackingRef '- 8 Cd aja0702.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common aja0702 _chemical_melting_point ? _chemical_formula_moiety 'C23 H17 Cd Cl N5 O5, C2 H3 N, Cl O4' _chemical_formula_sum 'C25 H20 Cd Cl2 N6 O9' _chemical_formula_weight 731.77 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' 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 7.29700(10) _cell_length_b 15.3263(3) _cell_length_c 25.3479(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.6780(10) _cell_angle_gamma 90.00 _cell_volume 2833.59(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 26518 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.715 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 1.023 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6183 _exptl_absorpt_correction_T_max 0.8063 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23459 _diffrn_reflns_av_R_equivalents 0.0740 _diffrn_reflns_av_sigmaI/netI 0.0626 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.44 _reflns_number_total 6451 _reflns_number_gt 4767 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0700P)^2^+6.4627P] 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 6451 _refine_ls_number_parameters 390 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0789 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1522 _refine_ls_wR_factor_gt 0.1373 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 C1 C -0.0117(7) 0.2248(3) -0.08922(18) 0.0314(11) Uani 1 1 d . . . C2 C 0.0543(6) 0.3133(3) -0.07233(18) 0.0276(10) Uani 1 1 d . . . C3 C 0.0796(7) 0.3744(4) -0.11159(19) 0.0347(12) Uani 1 1 d . . . H3 H 0.0453 0.3619 -0.1472 0.042 Uiso 1 1 calc R . . C4 C 0.1558(7) 0.4540(4) -0.0979(2) 0.0399(13) Uani 1 1 d . . . H4 H 0.1772 0.4968 -0.1241 0.048 Uiso 1 1 calc R . . C5 C 0.2001(6) 0.4703(3) -0.0456(2) 0.0328(11) Uani 1 1 d . . . H5 H 0.2531 0.5247 -0.0355 0.039 Uiso 1 1 calc R . . C6 C 0.1674(6) 0.4075(3) -0.00778(18) 0.0259(10) Uani 1 1 d . . . C7 C 0.2088(6) 0.4225(3) 0.04943(19) 0.0271(10) Uani 1 1 d . . . C8 C 0.3067(7) 0.4950(3) 0.0673(2) 0.0384(12) Uani 1 1 d . . . H8 H 0.3516 0.5367 0.0431 0.046 Uiso 1 1 calc R . . C9 C 0.3375(8) 0.5052(4) 0.1213(2) 0.0460(14) Uani 1 1 d . . . H9 H 0.4051 0.5540 0.1343 0.055 Uiso 1 1 calc R . . C10 C 0.2706(8) 0.4453(4) 0.1557(2) 0.0460(14) Uani 1 1 d . . . H10 H 0.2887 0.4522 0.1927 0.055 Uiso 1 1 calc R . . C11 C 0.1756(7) 0.3741(3) 0.13498(19) 0.0360(12) Uani 1 1 d . . . H11 H 0.1287 0.3321 0.1586 0.043 Uiso 1 1 calc R . . C12 C 0.0807(6) 0.1432(3) -0.06819(18) 0.0276(10) Uani 1 1 d . . . C13 C 0.1354(6) 0.0817(3) -0.10447(19) 0.0328(11) Uani 1 1 d . . . H13 H 0.1113 0.0902 -0.1411 0.039 Uiso 1 1 calc R . . C14 C 0.2248(7) 0.0084(3) -0.0868(2) 0.0349(12) Uani 1 1 d . . . H14 H 0.2637 -0.0348 -0.1108 0.042 Uiso 1 1 calc R . . C15 C 0.2575(6) -0.0015(3) -0.0326(2) 0.0335(11) Uani 1 1 d . . . H15 H 0.3217 -0.0511 -0.0193 0.040 Uiso 1 1 calc R . . C16 C 0.1959(6) 0.0612(3) 0.00147(18) 0.0245(9) Uani 1 1 d . . . C17 C 0.2207(6) 0.0523(3) 0.06029(19) 0.0272(10) Uani 1 1 d . . . C18 C 0.3041(7) -0.0199(3) 0.0832(2) 0.0358(12) Uani 1 1 d . . . H18 H 0.3472 -0.0661 0.0620 0.043 Uiso 1 1 calc R . . C19 C 0.3238(7) -0.0236(4) 0.1381(2) 0.0433(14) Uani 1 1 d . . . H19 H 0.3837 -0.0719 0.1546 0.052 Uiso 1 1 calc R . . C20 C 0.2571(7) 0.0422(4) 0.1680(2) 0.0404(13) Uani 1 1 d . . . H20 H 0.2692 0.0405 0.2054 0.048 Uiso 1 1 calc R . . C21 C 0.1716(7) 0.1117(3) 0.14281(19) 0.0333(11) Uani 1 1 d . . . H21 H 0.1220 0.1570 0.1636 0.040 Uiso 1 1 calc R . . C22 C -0.2749(7) 0.2456(3) 0.1519(2) 0.0345(12) Uani 1 1 d . . . C23 C -0.4035(10) 0.2516(4) 0.1942(3) 0.0580(18) Uani 1 1 d . . . H23A H -0.5289 0.2480 0.1794 0.087 Uiso 1 1 calc R . . H23B H -0.3867 0.3073 0.2126 0.087 Uiso 1 1 calc R . . H23C H -0.3819 0.2035 0.2190 0.087 Uiso 1 1 calc R . . C24 C 0.0800(9) 0.2465(4) 0.2778(2) 0.0444(14) Uani 1 1 d . . . C25 C -0.0498(10) 0.2387(4) 0.3195(3) 0.0565(17) Uani 1 1 d . . . H25A H -0.1382 0.2867 0.3170 0.085 Uiso 1 1 calc R . . H25B H 0.0157 0.2410 0.3538 0.085 Uiso 1 1 calc R . . H25C H -0.1148 0.1829 0.3161 0.085 Uiso 1 1 calc R . . N1 N 0.0963(5) 0.3296(2) -0.02103(14) 0.0230(8) Uani 1 1 d . . . N2 N 0.1476(5) 0.3623(3) 0.08313(15) 0.0275(8) Uani 1 1 d . . . N3 N 0.1112(5) 0.1339(2) -0.01569(14) 0.0228(8) Uani 1 1 d . . . N4 N 0.1560(5) 0.1173(2) 0.09020(14) 0.0257(8) Uani 1 1 d . . . N5 N -0.1753(6) 0.2404(3) 0.11865(18) 0.0398(11) Uani 1 1 d . . . N6 N 0.1780(10) 0.2527(4) 0.2455(2) 0.074(2) Uani 1 1 d . . . O1 O -0.1217(5) 0.2184(3) -0.12600(14) 0.0448(10) Uani 1 1 d . . . O2 O -0.2531(4) 0.2100(2) -0.00122(13) 0.0332(8) Uani 1 1 d . . . O3 O -0.5407(5) 0.2160(3) 0.03791(16) 0.0479(10) Uani 1 1 d . . . O4 O -0.3899(7) 0.3426(3) 0.0181(2) 0.0750(15) Uani 1 1 d . . . O5 O -0.5118(6) 0.2548(4) -0.05021(17) 0.092(2) Uani 1 1 d . . . O6 O -0.2139(13) 0.0606(5) 0.2070(3) 0.141(3) Uani 1 1 d . . . O7 O -0.4273(8) 0.0464(6) 0.2698(2) 0.114(3) Uani 1 1 d . . . O8 O -0.1387(9) 0.0087(7) 0.2883(3) 0.164(4) Uani 1 1 d . . . O9 O -0.3127(12) -0.0705(4) 0.2250(3) 0.135(3) Uani 1 1 d . . . Cl1 Cl -0.42743(15) 0.25634(7) 0.00070(5) 0.0272(3) Uani 1 1 d . . . Cl2 Cl -0.26317(19) 0.00409(10) 0.24954(5) 0.0438(3) Uani 1 1 d . . . Cd1 Cd 0.02800(4) 0.23565(2) 0.048366(12) 0.02366(13) 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 C1 0.029(3) 0.042(3) 0.023(2) -0.002(2) 0.0013(19) 0.000(2) C2 0.019(2) 0.037(3) 0.027(2) 0.004(2) 0.0037(18) 0.0079(19) C3 0.036(3) 0.044(3) 0.025(2) 0.009(2) 0.005(2) 0.012(2) C4 0.044(3) 0.038(3) 0.038(3) 0.017(2) 0.012(2) 0.011(2) C5 0.028(3) 0.023(3) 0.047(3) 0.007(2) 0.006(2) 0.001(2) C6 0.021(2) 0.023(2) 0.034(2) 0.0041(19) 0.0057(19) 0.0068(18) C7 0.019(2) 0.022(2) 0.040(3) -0.001(2) 0.0003(19) 0.0027(18) C8 0.038(3) 0.028(3) 0.050(3) -0.004(2) 0.001(2) -0.005(2) C9 0.039(3) 0.034(3) 0.064(4) -0.014(3) -0.006(3) -0.003(2) C10 0.046(3) 0.050(4) 0.041(3) -0.011(3) -0.012(3) 0.004(3) C11 0.043(3) 0.036(3) 0.029(2) 0.001(2) -0.003(2) 0.000(2) C12 0.022(2) 0.035(3) 0.026(2) -0.0006(19) -0.0012(18) -0.0058(19) C13 0.028(3) 0.041(3) 0.030(2) -0.011(2) 0.004(2) -0.010(2) C14 0.031(3) 0.034(3) 0.040(3) -0.015(2) 0.014(2) -0.009(2) C15 0.024(2) 0.025(3) 0.052(3) -0.005(2) 0.008(2) -0.0034(19) C16 0.016(2) 0.023(2) 0.035(2) -0.0005(19) 0.0034(18) -0.0042(17) C17 0.021(2) 0.024(2) 0.037(3) 0.002(2) 0.0004(19) -0.0044(18) C18 0.026(3) 0.027(3) 0.053(3) 0.006(2) -0.005(2) -0.001(2) C19 0.036(3) 0.036(3) 0.057(4) 0.015(3) -0.012(3) -0.002(2) C20 0.043(3) 0.041(3) 0.037(3) 0.010(2) -0.009(2) -0.008(3) C21 0.033(3) 0.034(3) 0.033(3) 0.005(2) -0.003(2) -0.003(2) C22 0.030(3) 0.040(3) 0.033(3) 0.002(2) 0.002(2) -0.001(2) C23 0.058(4) 0.067(5) 0.051(4) 0.000(3) 0.030(3) 0.001(3) C24 0.048(3) 0.055(4) 0.030(3) -0.004(2) -0.002(3) -0.006(3) C25 0.065(4) 0.061(4) 0.045(3) 0.007(3) 0.014(3) -0.005(3) N1 0.0188(18) 0.025(2) 0.0250(18) 0.0032(15) 0.0005(15) 0.0032(15) N2 0.029(2) 0.026(2) 0.028(2) -0.0013(16) -0.0038(16) -0.0011(16) N3 0.0162(18) 0.025(2) 0.0275(19) -0.0040(15) 0.0032(15) -0.0016(14) N4 0.025(2) 0.025(2) 0.0270(19) 0.0023(16) -0.0002(15) -0.0044(16) N5 0.034(2) 0.056(3) 0.030(2) -0.001(2) 0.002(2) -0.001(2) N6 0.078(5) 0.108(6) 0.038(3) -0.006(3) 0.016(3) -0.007(4) O1 0.043(2) 0.060(3) 0.0301(19) -0.0030(18) -0.0139(17) -0.0012(19) O2 0.0240(18) 0.038(2) 0.0379(19) -0.0070(15) -0.0017(14) 0.0081(14) O3 0.0273(19) 0.067(3) 0.050(2) 0.013(2) 0.0031(17) -0.0157(19) O4 0.079(3) 0.022(2) 0.126(4) -0.002(2) 0.032(3) 0.001(2) O5 0.036(3) 0.206(8) 0.032(2) 0.002(3) -0.007(2) 0.042(3) O6 0.233(9) 0.107(5) 0.086(5) 0.017(4) 0.063(5) 0.038(6) O7 0.084(4) 0.196(8) 0.062(3) -0.019(4) 0.006(3) 0.038(5) O8 0.079(4) 0.329(13) 0.081(4) -0.070(6) -0.042(4) 0.042(6) O9 0.225(9) 0.079(5) 0.102(5) -0.037(4) 0.012(5) -0.038(5) Cl1 0.0213(5) 0.0304(6) 0.0301(6) 0.0034(4) 0.0022(4) 0.0038(4) Cl2 0.0469(8) 0.0557(9) 0.0287(6) -0.0111(6) -0.0012(6) -0.0081(7) Cd1 0.0270(2) 0.0230(2) 0.02102(18) 0.00023(13) 0.00139(13) -0.00032(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.216(6) . ? C1 C2 1.498(7) . ? C1 C12 1.511(7) . ? C2 N1 1.350(6) . ? C2 C3 1.383(7) . ? C3 C4 1.381(8) . ? C3 H3 0.9500 . ? C4 C5 1.378(7) . ? C4 H4 0.9500 . ? C5 C6 1.384(6) . ? C5 H5 0.9500 . ? C6 N1 1.342(6) . ? C6 C7 1.490(7) . ? C7 N2 1.342(6) . ? C7 C8 1.390(7) . ? C8 C9 1.388(8) . ? C8 H8 0.9500 . ? C9 C10 1.366(8) . ? C9 H9 0.9500 . ? C10 C11 1.387(8) . ? C10 H10 0.9500 . ? C11 N2 1.336(6) . ? C11 H11 0.9500 . ? C12 N3 1.350(6) . ? C12 C13 1.384(7) . ? C13 C14 1.367(8) . ? C13 H13 0.9500 . ? C14 C15 1.395(7) . ? C14 H14 0.9500 . ? C15 C16 1.376(7) . ? C15 H15 0.9500 . ? C16 N3 1.340(6) . ? C16 C17 1.503(6) . ? C17 N4 1.346(6) . ? C17 C18 1.382(7) . ? C18 C19 1.397(8) . ? C18 H18 0.9500 . ? C19 C20 1.360(8) . ? C19 H19 0.9500 . ? C20 C21 1.381(7) . ? C20 H20 0.9500 . ? C21 N4 1.338(6) . ? C21 H21 0.9500 . ? C22 N5 1.133(7) . ? C22 C23 1.446(8) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 N6 1.108(8) . ? C24 C25 1.445(9) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? N1 Cd1 2.338(4) . ? N2 Cd1 2.294(4) . ? N3 Cd1 2.344(4) . ? N4 Cd1 2.286(4) . ? N5 Cd1 2.352(4) . ? O2 Cl1 1.459(3) . ? O2 Cd1 2.406(3) . ? O3 Cl1 1.414(4) . ? O4 Cl1 1.418(4) . ? O5 Cl1 1.414(4) . ? O6 Cl2 1.438(7) . ? O7 Cl2 1.468(6) . ? O8 Cl2 1.320(6) . ? O9 Cl2 1.346(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 O1 C1 C2 119.4(5) . . ? O1 C1 C12 118.8(5) . . ? C2 C1 C12 120.8(4) . . ? N1 C2 C3 122.5(5) . . ? N1 C2 C1 120.3(4) . . ? C3 C2 C1 117.1(4) . . ? C4 C3 C2 118.6(5) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C5 C4 C3 118.9(5) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 120.0(5) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? N1 C6 C5 121.3(4) . . ? N1 C6 C7 116.5(4) . . ? C5 C6 C7 122.2(4) . . ? N2 C7 C8 121.3(5) . . ? N2 C7 C6 116.9(4) . . ? C8 C7 C6 121.8(4) . . ? C9 C8 C7 118.6(5) . . ? C9 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? C10 C9 C8 120.2(5) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 118.1(5) . . ? C9 C10 H10 120.9 . . ? C11 C10 H10 120.9 . . ? N2 C11 C10 122.6(5) . . ? N2 C11 H11 118.7 . . ? C10 C11 H11 118.7 . . ? N3 C12 C13 122.7(5) . . ? N3 C12 C1 119.6(4) . . ? C13 C12 C1 117.6(4) . . ? C14 C13 C12 119.0(5) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C13 C14 C15 118.6(5) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? C16 C15 C14 119.5(5) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? N3 C16 C15 122.2(4) . . ? N3 C16 C17 116.0(4) . . ? C15 C16 C17 121.8(4) . . ? N4 C17 C18 120.9(5) . . ? N4 C17 C16 117.2(4) . . ? C18 C17 C16 121.9(4) . . ? C17 C18 C19 118.9(5) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C20 C19 C18 119.8(5) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C21 118.5(5) . . ? C19 C20 H20 120.7 . . ? C21 C20 H20 120.7 . . ? N4 C21 C20 122.4(5) . . ? N4 C21 H21 118.8 . . ? C20 C21 H21 118.8 . . ? N5 C22 C23 179.3(7) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N6 C24 C25 179.3(8) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C6 N1 C2 118.7(4) . . ? C6 N1 Cd1 116.7(3) . . ? C2 N1 Cd1 124.3(3) . . ? C11 N2 C7 119.3(4) . . ? C11 N2 Cd1 122.5(3) . . ? C7 N2 Cd1 117.8(3) . . ? C16 N3 C12 117.9(4) . . ? C16 N3 Cd1 117.0(3) . . ? C12 N3 Cd1 125.0(3) . . ? C21 N4 C17 119.5(4) . . ? C21 N4 Cd1 122.4(3) . . ? C17 N4 Cd1 118.1(3) . . ? C22 N5 Cd1 177.5(5) . . ? Cl1 O2 Cd1 129.4(2) . . ? O5 Cl1 O3 110.7(3) . . ? O5 Cl1 O4 112.1(4) . . ? O3 Cl1 O4 108.1(3) . . ? O5 Cl1 O2 108.6(2) . . ? O3 Cl1 O2 109.7(2) . . ? O4 Cl1 O2 107.7(3) . . ? O8 Cl2 O9 124.0(7) . . ? O8 Cl2 O6 110.2(6) . . ? O9 Cl2 O6 103.6(5) . . ? O8 Cl2 O7 105.5(4) . . ? O9 Cl2 O7 109.0(5) . . ? O6 Cl2 O7 102.7(4) . . ? N4 Cd1 N2 110.33(14) . . ? N4 Cd1 N1 138.08(13) . . ? N2 Cd1 N1 71.39(13) . . ? N4 Cd1 N3 71.53(13) . . ? N2 Cd1 N3 136.52(13) . . ? N1 Cd1 N3 79.81(13) . . ? N4 Cd1 N5 86.06(15) . . ? N2 Cd1 N5 85.65(15) . . ? N1 Cd1 N5 134.73(14) . . ? N3 Cd1 N5 136.65(14) . . ? N4 Cd1 O2 116.31(13) . . ? N2 Cd1 O2 130.37(13) . . ? N1 Cd1 O2 84.54(12) . . ? N3 Cd1 O2 76.34(12) . . ? N5 Cd1 O2 81.60(14) . . ? 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 C1 C2 N1 147.1(5) . . . . ? C12 C1 C2 N1 -44.1(6) . . . . ? O1 C1 C2 C3 -36.6(6) . . . . ? C12 C1 C2 C3 132.2(5) . . . . ? N1 C2 C3 C4 2.0(7) . . . . ? C1 C2 C3 C4 -174.3(4) . . . . ? C2 C3 C4 C5 -1.4(7) . . . . ? C3 C4 C5 C6 -0.3(7) . . . . ? C4 C5 C6 N1 1.4(7) . . . . ? C4 C5 C6 C7 -178.6(4) . . . . ? N1 C6 C7 N2 -9.3(6) . . . . ? C5 C6 C7 N2 170.7(4) . . . . ? N1 C6 C7 C8 170.5(4) . . . . ? C5 C6 C7 C8 -9.5(7) . . . . ? N2 C7 C8 C9 -1.2(7) . . . . ? C6 C7 C8 C9 179.0(5) . . . . ? C7 C8 C9 C10 -0.7(8) . . . . ? C8 C9 C10 C11 1.2(8) . . . . ? C9 C10 C11 N2 0.0(8) . . . . ? O1 C1 C12 N3 -141.4(5) . . . . ? C2 C1 C12 N3 49.8(6) . . . . ? O1 C1 C12 C13 40.5(7) . . . . ? C2 C1 C12 C13 -128.4(5) . . . . ? N3 C12 C13 C14 -0.2(7) . . . . ? C1 C12 C13 C14 177.9(4) . . . . ? C12 C13 C14 C15 0.0(7) . . . . ? C13 C14 C15 C16 1.4(7) . . . . ? C14 C15 C16 N3 -2.7(7) . . . . ? C14 C15 C16 C17 177.5(4) . . . . ? N3 C16 C17 N4 0.1(6) . . . . ? C15 C16 C17 N4 179.9(4) . . . . ? N3 C16 C17 C18 179.3(4) . . . . ? C15 C16 C17 C18 -0.9(7) . . . . ? N4 C17 C18 C19 -1.3(7) . . . . ? C16 C17 C18 C19 179.5(4) . . . . ? C17 C18 C19 C20 1.6(8) . . . . ? C18 C19 C20 C21 -0.2(8) . . . . ? C19 C20 C21 N4 -1.6(8) . . . . ? C5 C6 N1 C2 -0.9(6) . . . . ? C7 C6 N1 C2 179.2(4) . . . . ? C5 C6 N1 Cd1 -175.2(3) . . . . ? C7 C6 N1 Cd1 4.8(5) . . . . ? C3 C2 N1 C6 -0.9(6) . . . . ? C1 C2 N1 C6 175.3(4) . . . . ? C3 C2 N1 Cd1 173.0(3) . . . . ? C1 C2 N1 Cd1 -10.8(6) . . . . ? C10 C11 N2 C7 -1.9(8) . . . . ? C10 C11 N2 Cd1 170.9(4) . . . . ? C8 C7 N2 C11 2.5(7) . . . . ? C6 C7 N2 C11 -177.7(4) . . . . ? C8 C7 N2 Cd1 -170.6(4) . . . . ? C6 C7 N2 Cd1 9.2(5) . . . . ? C15 C16 N3 C12 2.4(6) . . . . ? C17 C16 N3 C12 -177.8(4) . . . . ? C15 C16 N3 Cd1 -177.4(3) . . . . ? C17 C16 N3 Cd1 2.3(5) . . . . ? C13 C12 N3 C16 -0.9(6) . . . . ? C1 C12 N3 C16 -179.0(4) . . . . ? C13 C12 N3 Cd1 178.9(3) . . . . ? C1 C12 N3 Cd1 0.8(6) . . . . ? C20 C21 N4 C17 2.0(7) . . . . ? C20 C21 N4 Cd1 -176.7(4) . . . . ? C18 C17 N4 C21 -0.5(7) . . . . ? C16 C17 N4 C21 178.8(4) . . . . ? C18 C17 N4 Cd1 178.2(3) . . . . ? C16 C17 N4 Cd1 -2.6(5) . . . . ? Cd1 O2 Cl1 O5 147.7(3) . . . . ? Cd1 O2 Cl1 O3 -91.2(3) . . . . ? Cd1 O2 Cl1 O4 26.2(4) . . . . ? C21 N4 Cd1 N2 47.6(4) . . . . ? C17 N4 Cd1 N2 -131.1(3) . . . . ? C21 N4 Cd1 N1 132.0(3) . . . . ? C17 N4 Cd1 N1 -46.6(4) . . . . ? C21 N4 Cd1 N3 -178.6(4) . . . . ? C17 N4 Cd1 N3 2.7(3) . . . . ? C21 N4 Cd1 N5 -36.3(4) . . . . ? C17 N4 Cd1 N5 145.0(3) . . . . ? C21 N4 Cd1 O2 -114.9(4) . . . . ? C17 N4 Cd1 O2 66.4(3) . . . . ? C11 N2 Cd1 N4 -42.3(4) . . . . ? C7 N2 Cd1 N4 130.5(3) . . . . ? C11 N2 Cd1 N1 -177.8(4) . . . . ? C7 N2 Cd1 N1 -4.9(3) . . . . ? C11 N2 Cd1 N3 -126.6(4) . . . . ? C7 N2 Cd1 N3 46.3(4) . . . . ? C11 N2 Cd1 N5 41.8(4) . . . . ? C7 N2 Cd1 N5 -145.3(3) . . . . ? C11 N2 Cd1 O2 116.9(4) . . . . ? C7 N2 Cd1 O2 -70.2(4) . . . . ? C6 N1 Cd1 N4 -100.3(3) . . . . ? C2 N1 Cd1 N4 85.7(4) . . . . ? C6 N1 Cd1 N2 -0.3(3) . . . . ? C2 N1 Cd1 N2 -174.3(4) . . . . ? C6 N1 Cd1 N3 -147.2(3) . . . . ? C2 N1 Cd1 N3 38.8(3) . . . . ? C6 N1 Cd1 N5 63.2(4) . . . . ? C2 N1 Cd1 N5 -110.8(4) . . . . ? C6 N1 Cd1 O2 135.7(3) . . . . ? C2 N1 Cd1 O2 -38.3(3) . . . . ? C16 N3 Cd1 N4 -2.7(3) . . . . ? C12 N3 Cd1 N4 177.5(4) . . . . ? C16 N3 Cd1 N2 97.7(3) . . . . ? C12 N3 Cd1 N2 -82.1(4) . . . . ? C16 N3 Cd1 N1 146.3(3) . . . . ? C12 N3 Cd1 N1 -33.5(3) . . . . ? C16 N3 Cd1 N5 -65.3(4) . . . . ? C12 N3 Cd1 N5 114.8(4) . . . . ? C16 N3 Cd1 O2 -126.9(3) . . . . ? C12 N3 Cd1 O2 53.3(3) . . . . ? Cl1 O2 Cd1 N4 128.8(3) . . . . ? Cl1 O2 Cd1 N2 -29.5(3) . . . . ? Cl1 O2 Cd1 N1 -89.4(3) . . . . ? Cl1 O2 Cd1 N3 -170.2(3) . . . . ? Cl1 O2 Cd1 N5 47.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.610 _refine_diff_density_min -0.917 _refine_diff_density_rms 0.135