# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Allan Blackman' _publ_contact_author_email blackman@alkali.otago.ac.nz _publ_section_title ; Factors influencing mononuclear versus multinuclear coordination in a series of potentially hexadentate acyclic N6 ligands: the roles of flexibility and chelate ring size. ; loop_ _publ_author_name N.Hall C.Duboc M.-N.Collomb A.Deronzier A.Blackman # Attachment '- Combined.cif' data_nh1 _database_code_depnum_ccdc_archive 'CCDC 821594' #TrackingRef '- Combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H26 Cl3 Co N6 O13' _chemical_formula_weight 783.80 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' 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.0350(15) _cell_length_b 11.3060(16) _cell_length_c 12.9580(16) _cell_angle_alpha 81.574(7) _cell_angle_beta 69.671(7) _cell_angle_gamma 75.012(7) _cell_volume 1461.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 89(2) _cell_measurement_reflns_used 7053 _cell_measurement_theta_min 4.336 _cell_measurement_theta_max 62.21 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.781 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.943 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.846624 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 89(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa ApexII area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41746 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5449 _reflns_number_gt 4914 _reflns_threshold_expression >2\s(I) _computing_data_collection 'ApexII (Bruker, 2004)' _computing_cell_refinement 'ApexII and SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'WinGX (Farrugia, 1999)' _computing_publication_material WinGX _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+0.8013P] 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 5449 _refine_ls_number_parameters 459 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0866 _refine_ls_wR_factor_gt 0.0819 _refine_ls_goodness_of_fit_ref 1.158 _refine_ls_restrained_S_all 1.158 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.76432(3) 0.28015(2) 0.23886(2) 0.01046(9) Uani 1 1 d . . . Cl2 Cl 0.35930(5) 0.14897(5) 0.22843(4) 0.01620(13) Uani 1 1 d . . . Cl3 Cl 1.03967(5) 0.22079(5) -0.15794(4) 0.01620(13) Uani 1 1 d . . . Cl1 Cl 0.67608(5) 0.31448(5) 0.64049(4) 0.01661(13) Uani 1 1 d . . . O9 O 1.00093(16) 0.12400(15) -0.07689(13) 0.0237(4) Uani 1 1 d . . . O6 O 0.45298(15) 0.07660(15) 0.28004(13) 0.0223(4) Uani 1 1 d . . . O7 O 0.22761(15) 0.16569(16) 0.30842(13) 0.0251(4) Uani 1 1 d . . . O10 O 1.03437(18) 0.32385(15) -0.10091(13) 0.0288(4) Uani 1 1 d . . . O3 O 0.81125(16) 0.27279(17) 0.57206(14) 0.0320(4) Uani 1 1 d . . . O4 O 0.60046(15) 0.37882(14) 0.56884(12) 0.0210(3) Uani 1 1 d . . . O8 O 0.36262(17) 0.08879(16) 0.13655(13) 0.0271(4) Uani 1 1 d . . . O11 O 1.17302(16) 0.17897(15) -0.22952(13) 0.0275(4) Uani 1 1 d . . . O5 O 0.39081(17) 0.26694(15) 0.18875(13) 0.0236(4) Uani 1 1 d . . . O2 O 0.66942(19) 0.39725(15) 0.71712(14) 0.0325(4) Uani 1 1 d . . . O12 O 0.95030(17) 0.25770(17) -0.22065(14) 0.0314(4) Uani 1 1 d . . . O1 O 0.62433(19) 0.21116(16) 0.69815(15) 0.0346(4) Uani 1 1 d . . . N2 N 0.82553(17) 0.13561(16) 0.31247(14) 0.0132(4) Uani 1 1 d . . . N6 N 0.72339(16) 0.21160(16) 0.12867(13) 0.0122(4) Uani 1 1 d . . . N5 N 0.70813(16) 0.42780(16) 0.16618(13) 0.0117(4) Uani 1 1 d . . . C10 C 0.9549(2) 0.08007(19) 0.27762(17) 0.0147(4) Uani 1 1 d . . . N1 N 0.59539(17) 0.26734(16) 0.34987(14) 0.0124(4) Uani 1 1 d . . . N3 N 0.95027(16) 0.25719(16) 0.14099(14) 0.0137(4) Uani 1 1 d . . . H3 H 0.9473 0.2481 0.0733 0.021(6) Uiso 1 1 calc R . . C23 C 0.9294(2) 0.3657(2) 0.33620(17) 0.0167(5) Uani 1 1 d . . . H23A H 0.9598 0.2800 0.3568 0.018(6) Uiso 1 1 calc R . . H23B H 0.9286 0.4138 0.3927 0.023(6) Uiso 1 1 calc R . . C5 C 0.6047(2) 0.17276(19) 0.42695(16) 0.0139(4) Uani 1 1 d . . . N4 N 0.79074(17) 0.38518(16) 0.33474(14) 0.0137(4) Uani 1 1 d . . . H4 H 0.7421 0.3645 0.4046 0.022(6) Uiso 1 1 calc R . . C16 C 0.69338(19) 0.29656(19) 0.04940(16) 0.0126(4) Uani 1 1 d . . . C17 C 0.68425(19) 0.42328(19) 0.07115(16) 0.0130(4) Uani 1 1 d . . . C21 C 0.70081(19) 0.53401(19) 0.20510(17) 0.0141(4) Uani 1 1 d . . . C19 C 0.6435(2) 0.6416(2) 0.05038(18) 0.0182(5) Uani 1 1 d . . . H19 H 0.6216 0.7147 0.0107 0.013(6) Uiso 1 1 calc R . . O13 O 1.0375(2) 0.38851(19) -0.43057(17) 0.0505(6) Uani 1 1 d . . . C24 C 1.0278(2) 0.3995(2) 0.22783(18) 0.0185(5) Uani 1 1 d . . . H24A H 1.1165 0.3615 0.2298 0.026(7) Uiso 1 1 calc R . . H24B H 1.0188 0.4876 0.2218 0.027(7) Uiso 1 1 calc R . . C3 C 0.3719(2) 0.2300(2) 0.52134(17) 0.0184(5) Uani 1 1 d . . . H3A H 0.2966 0.2183 0.5791 0.020(6) Uiso 1 1 calc R . . C6 C 0.7396(2) 0.09740(19) 0.40708(16) 0.0139(4) Uani 1 1 d . . . C13 C 0.6979(2) 0.0568(2) 0.03704(17) 0.0171(5) Uani 1 1 d . . . H13 H 0.6968 -0.0249 0.0354 0.022(6) Uiso 1 1 calc R . . C11 C 1.0320(2) 0.1361(2) 0.17116(17) 0.0164(5) Uani 1 1 d . . . H11A H 1.0573 0.0804 0.1131 0.022(6) Uiso 1 1 calc R . . H11B H 1.1124 0.1491 0.1779 0.022(6) Uiso 1 1 calc R . . C4 C 0.4945(2) 0.1529(2) 0.51446(17) 0.0171(5) Uani 1 1 d . . . H4A H 0.5026 0.0891 0.5675 0.028(7) Uiso 1 1 calc R . . C14 C 0.6724(2) 0.1413(2) -0.04528(17) 0.0186(5) Uani 1 1 d . . . H14 H 0.6567 0.1168 -0.1041 0.014(6) Uiso 1 1 calc R . . C9 C 1.0040(2) -0.0196(2) 0.33920(18) 0.0187(5) Uani 1 1 d . . . H9 H 1.0933 -0.0588 0.3160 0.032(7) Uiso 1 1 calc R . . C18 C 0.6528(2) 0.5305(2) 0.01028(18) 0.0174(5) Uani 1 1 d . . . H18 H 0.6382 0.5287 -0.0559 0.030(7) Uiso 1 1 calc R . . C2 C 0.3628(2) 0.3243(2) 0.44159(17) 0.0184(5) Uani 1 1 d . . . H2 H 0.2811 0.3758 0.4444 0.020(6) Uiso 1 1 calc R . . C22 C 0.7295(2) 0.51718(19) 0.31215(17) 0.0159(4) Uani 1 1 d . . . H22A H 0.6478 0.5430 0.3718 0.018(6) Uiso 1 1 calc R . . H22B H 0.7895 0.5680 0.3088 0.020(6) Uiso 1 1 calc R . . C8 C 0.9172(2) -0.0597(2) 0.43613(18) 0.0206(5) Uani 1 1 d . . . H8 H 0.9489 -0.1265 0.4782 0.026(7) Uiso 1 1 calc R . . C7 C 0.7837(2) -0.00153(19) 0.47133(18) 0.0180(5) Uani 1 1 d . . . H7 H 0.7257 -0.0285 0.5364 0.023(6) Uiso 1 1 calc R . . C20 C 0.6665(2) 0.6444(2) 0.14867(18) 0.0172(5) Uani 1 1 d . . . H20 H 0.6590 0.7186 0.1759 0.017(6) Uiso 1 1 calc R . . C12 C 0.72501(19) 0.09407(19) 0.12228(17) 0.0140(4) Uani 1 1 d . . . H12 H 0.7448 0.0361 0.1763 0.010(5) Uiso 1 1 calc R . . C1 C 0.4766(2) 0.34131(19) 0.35745(17) 0.0146(4) Uani 1 1 d . . . H1 H 0.4704 0.4059 0.3047 0.008(5) Uiso 1 1 calc R . . C15 C 0.6705(2) 0.2631(2) -0.03922(17) 0.0164(5) Uani 1 1 d . . . H15 H 0.6540 0.3215 -0.0941 0.013(6) Uiso 1 1 calc R . . C25 C 1.0142(2) 0.3626(2) 0.12444(17) 0.0172(5) Uani 1 1 d . . . H25A H 0.9630 0.4330 0.0938 0.017(6) Uiso 1 1 calc R . . H25B H 1.1019 0.3423 0.0704 0.015(6) Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.01125(15) 0.01129(16) 0.00856(15) -0.00035(11) -0.00291(11) -0.00264(11) Cl2 0.0168(3) 0.0193(3) 0.0141(2) 0.0025(2) -0.0063(2) -0.0066(2) Cl3 0.0189(3) 0.0157(3) 0.0125(2) -0.0001(2) -0.0033(2) -0.0041(2) Cl1 0.0181(3) 0.0159(3) 0.0138(2) 0.0000(2) -0.0048(2) -0.0016(2) O9 0.0243(8) 0.0208(8) 0.0216(8) 0.0046(7) -0.0024(7) -0.0075(7) O6 0.0178(8) 0.0265(9) 0.0218(8) 0.0052(7) -0.0095(7) -0.0030(7) O7 0.0162(8) 0.0345(10) 0.0202(8) 0.0067(7) -0.0053(7) -0.0038(7) O10 0.0445(11) 0.0208(9) 0.0224(8) -0.0036(7) -0.0095(8) -0.0104(8) O3 0.0191(9) 0.0377(10) 0.0285(9) 0.0032(8) -0.0029(7) 0.0024(7) O4 0.0231(8) 0.0225(8) 0.0185(8) -0.0014(6) -0.0111(7) -0.0010(7) O8 0.0344(10) 0.0317(10) 0.0227(8) -0.0051(7) -0.0126(8) -0.0136(8) O11 0.0212(8) 0.0285(9) 0.0227(8) 0.0011(7) 0.0034(7) -0.0046(7) O5 0.0343(9) 0.0208(8) 0.0205(8) 0.0056(7) -0.0121(7) -0.0134(7) O2 0.0537(12) 0.0237(9) 0.0265(9) -0.0040(7) -0.0265(9) 0.0003(8) O12 0.0321(10) 0.0391(10) 0.0237(9) -0.0003(8) -0.0153(8) -0.0015(8) O1 0.0441(11) 0.0275(10) 0.0303(10) 0.0100(8) -0.0085(8) -0.0161(8) N2 0.0152(9) 0.0144(9) 0.0117(8) -0.0021(7) -0.0056(7) -0.0038(7) N6 0.0093(8) 0.0158(9) 0.0106(8) -0.0024(7) -0.0013(7) -0.0031(7) N5 0.0095(8) 0.0147(9) 0.0105(8) 0.0003(7) -0.0020(7) -0.0041(7) C10 0.0155(10) 0.0162(11) 0.0160(10) -0.0049(8) -0.0084(9) -0.0032(8) N1 0.0148(9) 0.0131(9) 0.0107(8) -0.0035(7) -0.0043(7) -0.0036(7) N3 0.0134(9) 0.0159(9) 0.0118(8) -0.0002(7) -0.0040(7) -0.0034(7) C23 0.0189(11) 0.0176(11) 0.0181(11) 0.0008(9) -0.0115(9) -0.0052(9) C5 0.0205(11) 0.0129(10) 0.0098(9) -0.0020(8) -0.0044(8) -0.0063(9) N4 0.0166(9) 0.0148(9) 0.0102(8) -0.0001(7) -0.0036(7) -0.0055(7) C16 0.0100(9) 0.0163(11) 0.0098(9) 0.0005(8) -0.0010(8) -0.0036(8) C17 0.0076(9) 0.0191(11) 0.0112(10) -0.0005(8) -0.0020(8) -0.0027(8) C21 0.0096(9) 0.0149(11) 0.0154(10) -0.0023(8) -0.0004(8) -0.0029(8) C19 0.0122(10) 0.0168(11) 0.0211(11) 0.0073(9) -0.0033(9) -0.0031(9) O13 0.0761(16) 0.0352(11) 0.0386(11) -0.0005(9) -0.0109(11) -0.0213(11) C24 0.0167(11) 0.0160(11) 0.0257(12) -0.0008(9) -0.0090(9) -0.0061(9) C3 0.0188(11) 0.0219(12) 0.0139(10) -0.0068(9) 0.0021(9) -0.0110(9) C6 0.0192(11) 0.0142(10) 0.0110(10) -0.0015(8) -0.0054(8) -0.0073(8) C13 0.0138(10) 0.0178(11) 0.0187(11) -0.0068(9) -0.0006(9) -0.0052(9) C11 0.0124(10) 0.0177(11) 0.0189(11) -0.0038(9) -0.0065(9) 0.0003(8) C4 0.0263(12) 0.0141(11) 0.0133(10) -0.0011(9) -0.0053(9) -0.0102(9) C14 0.0147(10) 0.0275(12) 0.0149(10) -0.0071(9) -0.0041(9) -0.0049(9) C9 0.0198(11) 0.0159(11) 0.0242(12) -0.0056(9) -0.0127(10) -0.0005(9) C18 0.0123(10) 0.0237(12) 0.0151(10) 0.0051(9) -0.0045(8) -0.0056(9) C2 0.0167(11) 0.0191(11) 0.0184(11) -0.0087(9) -0.0017(9) -0.0037(9) C22 0.0169(11) 0.0139(11) 0.0156(10) -0.0033(8) -0.0032(9) -0.0031(8) C8 0.0307(13) 0.0139(11) 0.0215(11) 0.0026(9) -0.0170(10) -0.0024(9) C7 0.0263(12) 0.0147(11) 0.0167(11) 0.0017(9) -0.0104(9) -0.0077(9) C20 0.0121(10) 0.0132(11) 0.0233(11) 0.0002(9) -0.0019(9) -0.0040(8) C12 0.0117(10) 0.0131(10) 0.0151(10) -0.0017(8) -0.0025(8) -0.0011(8) C1 0.0167(11) 0.0144(11) 0.0131(10) -0.0037(8) -0.0035(8) -0.0042(8) C15 0.0112(10) 0.0240(12) 0.0129(10) -0.0006(9) -0.0032(8) -0.0032(9) C25 0.0128(10) 0.0199(12) 0.0182(11) 0.0028(9) -0.0037(9) -0.0064(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N2 1.8592(18) . ? Co1 N5 1.8621(17) . ? Co1 N1 1.9444(17) . ? Co1 N6 1.9485(17) . ? Co1 N3 1.9746(17) . ? Co1 N4 1.9753(17) . ? Cl2 O6 1.4381(16) . ? Cl2 O5 1.4419(17) . ? Cl2 O8 1.4408(16) . ? Cl2 O7 1.4459(16) . ? Cl3 O12 1.4323(18) . ? Cl3 O11 1.4387(16) . ? Cl3 O9 1.4410(16) . ? Cl3 O10 1.4471(17) . ? Cl1 O1 1.4288(18) . ? Cl1 O2 1.4329(17) . ? Cl1 O3 1.4398(17) . ? Cl1 O4 1.4539(16) . ? N2 C10 1.344(3) . ? N2 C6 1.355(3) . ? N6 C12 1.339(3) . ? N6 C16 1.368(3) . ? N5 C21 1.342(3) . ? N5 C17 1.356(3) . ? C10 C9 1.387(3) . ? C10 C11 1.495(3) . ? N1 C1 1.340(3) . ? N1 C5 1.361(3) . ? N3 C25 1.490(3) . ? N3 C11 1.514(3) . ? N3 H3 0.9100 . ? C23 N4 1.495(3) . ? C23 C24 1.515(3) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C5 C4 1.387(3) . ? C5 C6 1.466(3) . ? N4 C22 1.502(3) . ? N4 H4 0.9100 . ? C16 C15 1.380(3) . ? C16 C17 1.472(3) . ? C17 C18 1.380(3) . ? C21 C20 1.385(3) . ? C21 C22 1.502(3) . ? C19 C20 1.389(3) . ? C19 C18 1.395(3) . ? C19 H19 0.9300 . ? C24 C25 1.525(3) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C3 C2 1.381(3) . ? C3 C4 1.388(3) . ? C3 H3A 0.9300 . ? C6 C7 1.381(3) . ? C13 C14 1.379(3) . ? C13 C12 1.385(3) . ? C13 H13 0.9300 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C4 H4A 0.9300 . ? C14 C15 1.385(3) . ? C14 H14 0.9300 . ? C9 C8 1.386(3) . ? C9 H9 0.9300 . ? C18 H18 0.9300 . ? C2 C1 1.383(3) . ? C2 H2 0.9300 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C8 C7 1.389(3) . ? C8 H8 0.9300 . ? C7 H7 0.9300 . ? C20 H20 0.9300 . ? C12 H12 0.9300 . ? C1 H1 0.9300 . ? C15 H15 0.9300 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Co1 N5 177.61(7) . . ? N2 Co1 N1 82.57(7) . . ? N5 Co1 N1 98.74(7) . . ? N2 Co1 N6 99.47(7) . . ? N5 Co1 N6 82.50(7) . . ? N1 Co1 N6 92.17(7) . . ? N2 Co1 N3 84.72(7) . . ? N5 Co1 N3 94.00(7) . . ? N1 Co1 N3 167.24(7) . . ? N6 Co1 N3 88.76(7) . . ? N2 Co1 N4 93.40(7) . . ? N5 Co1 N4 84.64(7) . . ? N1 Co1 N4 89.20(7) . . ? N6 Co1 N4 167.13(7) . . ? N3 Co1 N4 92.73(7) . . ? O6 Cl2 O5 109.85(10) . . ? O6 Cl2 O8 110.76(10) . . ? O5 Cl2 O8 108.61(10) . . ? O6 Cl2 O7 109.00(9) . . ? O5 Cl2 O7 109.54(10) . . ? O8 Cl2 O7 109.07(10) . . ? O12 Cl3 O11 110.26(10) . . ? O12 Cl3 O9 109.83(11) . . ? O11 Cl3 O9 109.71(10) . . ? O12 Cl3 O10 109.45(11) . . ? O11 Cl3 O10 109.20(11) . . ? O9 Cl3 O10 108.35(10) . . ? O1 Cl1 O2 110.25(11) . . ? O1 Cl1 O3 109.34(11) . . ? O2 Cl1 O3 110.25(12) . . ? O1 Cl1 O4 110.16(11) . . ? O2 Cl1 O4 109.09(10) . . ? O3 Cl1 O4 107.70(10) . . ? C10 N2 C6 122.10(18) . . ? C10 N2 Co1 119.59(14) . . ? C6 N2 Co1 117.92(14) . . ? C12 N6 C16 119.00(18) . . ? C12 N6 Co1 127.37(15) . . ? C16 N6 Co1 113.61(13) . . ? C21 N5 C17 122.34(18) . . ? C21 N5 Co1 119.41(14) . . ? C17 N5 Co1 118.10(14) . . ? N2 C10 C9 119.91(19) . . ? N2 C10 C11 113.56(18) . . ? C9 C10 C11 126.53(19) . . ? C1 N1 C5 119.23(18) . . ? C1 N1 Co1 126.93(15) . . ? C5 N1 Co1 113.83(14) . . ? C25 N3 C11 113.85(16) . . ? C25 N3 Co1 116.62(13) . . ? C11 N3 Co1 110.45(13) . . ? C25 N3 H3 104.9 . . ? C11 N3 H3 104.9 . . ? Co1 N3 H3 104.9 . . ? N4 C23 C24 114.71(17) . . ? N4 C23 H23A 108.6 . . ? C24 C23 H23A 108.6 . . ? N4 C23 H23B 108.6 . . ? C24 C23 H23B 108.6 . . ? H23A C23 H23B 107.6 . . ? N1 C5 C4 121.5(2) . . ? N1 C5 C6 113.50(18) . . ? C4 C5 C6 125.0(2) . . ? C23 N4 C22 113.23(16) . . ? C23 N4 Co1 115.83(13) . . ? C22 N4 Co1 110.02(13) . . ? C23 N4 H4 105.6 . . ? C22 N4 H4 105.6 . . ? Co1 N4 H4 105.6 . . ? N6 C16 C15 121.55(19) . . ? N6 C16 C17 113.41(17) . . ? C15 C16 C17 125.01(19) . . ? N5 C17 C18 119.82(19) . . ? N5 C17 C16 111.56(18) . . ? C18 C17 C16 128.60(19) . . ? N5 C21 C20 120.21(19) . . ? N5 C21 C22 113.20(18) . . ? C20 C21 C22 126.58(19) . . ? C20 C19 C18 120.9(2) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C23 C24 C25 115.83(18) . . ? C23 C24 H24A 108.3 . . ? C25 C24 H24A 108.3 . . ? C23 C24 H24B 108.3 . . ? C25 C24 H24B 108.3 . . ? H24A C24 H24B 107.4 . . ? C2 C3 C4 119.4(2) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? N2 C6 C7 120.20(19) . . ? N2 C6 C5 111.67(18) . . ? C7 C6 C5 128.13(19) . . ? C14 C13 C12 119.7(2) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C10 C11 N3 110.58(16) . . ? C10 C11 H11A 109.5 . . ? N3 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? N3 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C3 C4 C5 118.7(2) . . ? C3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? C13 C14 C15 119.1(2) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C8 C9 C10 118.6(2) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? C17 C18 C19 118.4(2) . . ? C17 C18 H18 120.8 . . ? C19 C18 H18 120.8 . . ? C3 C2 C1 119.3(2) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C21 C22 N4 110.62(16) . . ? C21 C22 H22A 109.5 . . ? N4 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? N4 C22 H22B 109.5 . . ? H22A C22 H22B 108.1 . . ? C9 C8 C7 121.0(2) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C6 C7 C8 118.2(2) . . ? C6 C7 H7 120.9 . . ? C8 C7 H7 120.9 . . ? C19 C20 C21 118.3(2) . . ? C19 C20 H20 120.9 . . ? C21 C20 H20 120.9 . . ? N6 C12 C13 121.5(2) . . ? N6 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? N1 C1 C2 121.8(2) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C16 C15 C14 119.1(2) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? N3 C25 C24 115.41(17) . . ? N3 C25 H25A 108.4 . . ? C24 C25 H25A 108.4 . . ? N3 C25 H25B 108.4 . . ? C24 C25 H25B 108.4 . . ? H25A C25 H25B 107.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.532 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.075 #===END data_nh21 _database_code_depnum_ccdc_archive 'CCDC 821595' #TrackingRef '- Combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H24 Cl2 Fe N6 O8' _chemical_formula_weight 651.24 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.5489(14) _cell_length_b 13.2220(11) _cell_length_c 11.8908(10) _cell_angle_alpha 90.00 _cell_angle_beta 110.802(5) _cell_angle_gamma 90.00 _cell_volume 2579.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 89(2) _cell_measurement_reflns_used 3385 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 23.93 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.90 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.677 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 0.855 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.862614 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 89(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 Kappa ApexII area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8803 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 24.12 _reflns_number_total 1982 _reflns_number_gt 1647 _reflns_threshold_expression >2\s(I) _computing_data_collection 'ApexII (Bruker, 2004)' _computing_cell_refinement 'ApexII and SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'WinGX (Farrugia, 1999)' _computing_publication_material WinGX _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+4.4916P] 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 1982 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0935 _refine_ls_wR_factor_gt 0.0877 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 Fe1 Fe 0.5000 0.22814(4) 0.7500 0.0141(2) Uani 1 2 d S . . Cl2 Cl 0.32965(5) 0.16549(6) 0.32145(6) 0.0199(2) Uani 1 1 d . . . O3 O 0.29939(13) 0.21952(16) 0.40195(19) 0.0243(5) Uani 1 1 d . . . N1 N 0.44359(15) 0.32860(18) 0.6283(2) 0.0179(6) Uani 1 1 d . . . O4 O 0.36714(18) 0.2340(2) 0.2647(2) 0.0525(8) Uani 1 1 d . . . O2 O 0.26413(14) 0.11421(17) 0.2305(2) 0.0321(6) Uani 1 1 d . . . C5 C 0.47402(19) 0.3390(2) 0.5376(3) 0.0194(7) Uani 1 1 d . . . O1 O 0.38838(16) 0.0928(2) 0.3902(2) 0.0471(8) Uani 1 1 d . . . C2 C 0.3429(2) 0.4533(2) 0.5329(3) 0.0255(8) Uani 1 1 d . . . H4A H 0.2984 0.4916 0.5328 0.031 Uiso 1 1 calc R . . C1 C 0.37887(19) 0.3859(2) 0.6244(3) 0.0216(7) Uani 1 1 d . . . H5 H 0.3579 0.3794 0.6858 0.026 Uiso 1 1 calc R . . C3 C 0.3733(2) 0.4638(2) 0.4414(3) 0.0258(8) Uani 1 1 d . . . H3 H 0.3498 0.5096 0.3793 0.031 Uiso 1 1 calc R . . C4 C 0.4389(2) 0.4060(2) 0.4427(3) 0.0244(8) Uani 1 1 d . . . H2 H 0.4595 0.4116 0.3810 0.029 Uiso 1 1 calc R . . N2 N 0.56783(15) 0.22352(18) 0.6580(2) 0.0152(6) Uani 1 1 d . . . N3 N 0.57377(15) 0.11543(18) 0.8431(2) 0.0164(6) Uani 1 1 d . . . H4B H 0.5881 0.1285 0.9231 0.020 Uiso 1 1 calc R . . C6 C 0.54542(19) 0.2752(2) 0.5525(3) 0.0177(7) Uani 1 1 d . . . C9 C 0.67816(19) 0.1479(2) 0.6179(3) 0.0230(8) Uani 1 1 d . . . H9A H 0.7232 0.1051 0.6410 0.028 Uiso 1 1 calc R . . C7 C 0.58814(19) 0.2632(2) 0.4757(3) 0.0227(8) Uani 1 1 d . . . H7A H 0.5722 0.2974 0.4026 0.027 Uiso 1 1 calc R . . C12 C 0.52684(19) 0.0195(2) 0.8156(3) 0.0201(7) Uani 1 1 d . . . H25C H 0.4936 0.0135 0.8654 0.024 Uiso 1 1 calc R . . H25D H 0.5639 -0.0377 0.8325 0.024 Uiso 1 1 calc R . . C8 C 0.6550(2) 0.1995(3) 0.5093(3) 0.0254(8) Uani 1 1 d . . . H8A H 0.6847 0.1911 0.4587 0.030 Uiso 1 1 calc R . . C11 C 0.64962(18) 0.1142(2) 0.8124(3) 0.0186(7) Uani 1 1 d . . . H15C H 0.6679 0.0451 0.8117 0.022 Uiso 1 1 calc R . . H15D H 0.6925 0.1514 0.8729 0.022 Uiso 1 1 calc R . . C10 C 0.63290(18) 0.1615(2) 0.6913(3) 0.0177(7) 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 Fe1 0.0157(4) 0.0112(3) 0.0141(3) 0.000 0.0037(3) 0.000 Cl2 0.0209(5) 0.0203(4) 0.0172(4) -0.0024(3) 0.0049(3) 0.0007(3) O3 0.0245(13) 0.0219(13) 0.0285(12) -0.0087(10) 0.0118(11) 0.0034(10) N1 0.0167(15) 0.0133(14) 0.0188(13) -0.0023(11) 0.0004(11) -0.0020(11) O4 0.076(2) 0.0606(19) 0.0322(14) -0.0125(14) 0.0329(15) -0.0401(16) O2 0.0279(14) 0.0294(14) 0.0321(13) -0.0132(11) 0.0023(11) -0.0033(11) C5 0.0181(18) 0.0127(17) 0.0200(15) -0.0005(14) -0.0022(14) -0.0066(13) O1 0.0543(18) 0.0521(17) 0.0237(12) -0.0065(12) 0.0002(12) 0.0338(15) C2 0.0220(19) 0.0145(17) 0.0332(18) -0.0020(16) 0.0014(16) 0.0010(14) C1 0.0206(19) 0.0155(17) 0.0252(17) -0.0040(14) 0.0038(15) -0.0010(14) C3 0.024(2) 0.0136(17) 0.0280(17) 0.0052(15) -0.0050(15) -0.0039(15) C4 0.027(2) 0.0194(18) 0.0209(16) 0.0031(15) 0.0013(15) -0.0091(15) N2 0.0158(14) 0.0124(13) 0.0151(12) -0.0012(11) 0.0027(11) -0.0020(11) N3 0.0194(15) 0.0161(14) 0.0142(12) -0.0009(11) 0.0064(11) -0.0005(11) C6 0.0191(18) 0.0153(17) 0.0157(15) -0.0001(13) 0.0025(13) -0.0059(13) C9 0.0184(18) 0.0243(18) 0.0255(17) -0.0058(15) 0.0068(15) -0.0005(14) C7 0.027(2) 0.0246(19) 0.0151(15) -0.0024(14) 0.0056(15) -0.0089(15) C12 0.0196(19) 0.0118(16) 0.0276(18) 0.0032(14) 0.0067(15) -0.0003(13) C8 0.027(2) 0.031(2) 0.0221(16) -0.0095(16) 0.0140(15) -0.0093(16) C11 0.0165(17) 0.0153(17) 0.0234(16) 0.0012(14) 0.0064(14) 0.0013(13) C10 0.0142(17) 0.0154(17) 0.0212(15) -0.0045(14) 0.0034(13) -0.0044(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N2 1.883(2) . ? Fe1 N2 1.883(2) 2_656 ? Fe1 N1 1.955(2) 2_656 ? Fe1 N1 1.955(2) . ? Fe1 N3 2.026(2) 2_656 ? Fe1 N3 2.026(2) . ? Cl2 O4 1.423(3) . ? Cl2 O1 1.434(2) . ? Cl2 O2 1.438(2) . ? Cl2 O3 1.439(2) . ? N1 C1 1.352(4) . ? N1 C5 1.369(4) . ? C5 C4 1.394(4) . ? C5 C6 1.468(4) . ? C2 C1 1.374(4) . ? C2 C3 1.379(5) . ? C2 H4A 0.9300 . ? C1 H5 0.9300 . ? C3 C4 1.376(5) . ? C3 H3 0.9300 . ? C4 H2 0.9300 . ? N2 C10 1.346(4) . ? N2 C6 1.358(4) . ? N3 C12 1.485(4) . ? N3 C11 1.500(4) . ? N3 H4B 0.9100 . ? C6 C7 1.381(4) . ? C9 C10 1.384(4) . ? C9 C8 1.388(4) . ? C9 H9A 0.9300 . ? C7 C8 1.384(5) . ? C7 H7A 0.9300 . ? C12 C12 1.509(6) 2_656 ? C12 H25C 0.9700 . ? C12 H25D 0.9700 . ? C8 H8A 0.9300 . ? C11 C10 1.500(4) . ? C11 H15C 0.9700 . ? C11 H15D 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Fe1 N2 176.28(15) . 2_656 ? N2 Fe1 N1 101.19(10) . 2_656 ? N2 Fe1 N1 81.37(10) 2_656 2_656 ? N2 Fe1 N1 81.37(10) . . ? N2 Fe1 N1 101.19(10) 2_656 . ? N1 Fe1 N1 94.40(14) 2_656 . ? N2 Fe1 N3 94.11(10) . 2_656 ? N2 Fe1 N3 83.14(10) 2_656 2_656 ? N1 Fe1 N3 164.09(10) 2_656 2_656 ? N1 Fe1 N3 92.17(10) . 2_656 ? N2 Fe1 N3 83.14(10) . . ? N2 Fe1 N3 94.11(10) 2_656 . ? N1 Fe1 N3 92.17(10) 2_656 . ? N1 Fe1 N3 164.09(10) . . ? N3 Fe1 N3 85.29(14) 2_656 . ? O4 Cl2 O1 109.71(19) . . ? O4 Cl2 O2 108.93(15) . . ? O1 Cl2 O2 109.47(15) . . ? O4 Cl2 O3 110.00(15) . . ? O1 Cl2 O3 108.31(14) . . ? O2 Cl2 O3 110.42(13) . . ? C1 N1 C5 118.3(3) . . ? C1 N1 Fe1 127.2(2) . . ? C5 N1 Fe1 114.5(2) . . ? N1 C5 C4 121.1(3) . . ? N1 C5 C6 113.7(3) . . ? C4 C5 C6 125.2(3) . . ? C1 C2 C3 119.5(3) . . ? C1 C2 H4A 120.2 . . ? C3 C2 H4A 120.2 . . ? N1 C1 C2 122.3(3) . . ? N1 C1 H5 118.9 . . ? C2 C1 H5 118.9 . . ? C4 C3 C2 119.4(3) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 119.3(3) . . ? C3 C4 H2 120.3 . . ? C5 C4 H2 120.3 . . ? C10 N2 C6 121.0(3) . . ? C10 N2 Fe1 119.6(2) . . ? C6 N2 Fe1 119.0(2) . . ? C12 N3 C11 114.1(2) . . ? C12 N3 Fe1 108.15(17) . . ? C11 N3 Fe1 108.94(17) . . ? C12 N3 H4B 108.5 . . ? C11 N3 H4B 108.5 . . ? Fe1 N3 H4B 108.5 . . ? N2 C6 C7 120.4(3) . . ? N2 C6 C5 110.8(3) . . ? C7 C6 C5 128.8(3) . . ? C10 C9 C8 118.7(3) . . ? C10 C9 H9A 120.7 . . ? C8 C9 H9A 120.7 . . ? C6 C7 C8 118.9(3) . . ? C6 C7 H7A 120.6 . . ? C8 C7 H7A 120.6 . . ? N3 C12 C12 108.76(19) . 2_656 ? N3 C12 H25C 109.9 . . ? C12 C12 H25C 109.9 2_656 . ? N3 C12 H25D 109.9 . . ? C12 C12 H25D 109.9 2_656 . ? H25C C12 H25D 108.3 . . ? C7 C8 C9 120.3(3) . . ? C7 C8 H8A 119.8 . . ? C9 C8 H8A 119.8 . . ? N3 C11 C10 110.0(2) . . ? N3 C11 H15C 109.7 . . ? C10 C11 H15C 109.7 . . ? N3 C11 H15D 109.7 . . ? C10 C11 H15D 109.7 . . ? H15C C11 H15D 108.2 . . ? N2 C10 C9 120.7(3) . . ? N2 C10 C11 113.1(3) . . ? C9 C10 C11 126.2(3) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 24.12 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.306 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.070 #===END data_test1 _database_code_depnum_ccdc_archive 'CCDC 821596' #TrackingRef '- Combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H24 Cl2 Mn N6 O8' _chemical_formula_weight 650.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 18.217(8) _cell_length_b 8.519(4) _cell_length_c 17.009(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2640(2) _cell_formula_units_Z 4 _cell_measurement_temperature 89(2) _cell_measurement_reflns_used 7161 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 19.14 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1332 _exptl_absorpt_coefficient_mu 0.764 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.911036 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 89(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa ApexII area dtector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 46429 _diffrn_reflns_av_R_equivalents 0.0642 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 26.36 _reflns_number_total 2690 _reflns_number_gt 2301 _reflns_threshold_expression >2\s(I) _computing_data_collection 'ApexII (Bruker, 2004)' _computing_cell_refinement 'Apex and SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'WinGX (Farrugia, 1999)' _computing_publication_material WinGX _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+3.0262P] 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 2690 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1039 _refine_ls_wR_factor_gt 0.0987 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.5000 0.03783(6) 0.2500 0.02045(16) Uani 1 2 d S . . Cl1 Cl 0.36328(3) 0.20255(7) 0.02565(3) 0.02447(17) Uani 1 1 d . . . O3 O 0.29686(10) 0.1182(2) 0.00912(12) 0.0386(5) Uani 1 1 d . . . O4 O 0.42594(10) 0.0994(2) 0.02082(11) 0.0336(4) Uani 1 1 d . . . N2 N 0.38175(10) 0.0373(2) 0.28376(12) 0.0208(4) Uani 1 1 d . . . O6 O 0.37193(10) 0.3292(2) -0.03038(11) 0.0330(4) Uani 1 1 d . . . O1 O 0.35992(10) 0.2682(2) 0.10477(10) 0.0305(4) Uani 1 1 d . . . N3 N 0.48093(11) 0.2458(3) 0.33369(13) 0.0272(5) Uani 1 1 d . . . H3 H 0.5218 0.2606 0.3635 0.033 Uiso 1 1 calc R . . N1 N 0.44214(10) -0.1358(2) 0.17385(11) 0.0207(4) Uani 1 1 d . . . C6 C 0.33356(13) -0.0448(3) 0.23975(14) 0.0210(5) Uani 1 1 d . . . C5 C 0.36803(13) -0.1469(3) 0.17880(14) 0.0213(5) Uani 1 1 d . . . C11 C 0.41768(14) 0.2169(3) 0.38590(15) 0.0290(6) Uani 1 1 d . . . H11A H 0.3988 0.3162 0.4052 0.035 Uiso 1 1 calc R . . H11B H 0.4333 0.1551 0.4308 0.035 Uiso 1 1 calc R . . C9 C 0.28343(14) 0.1421(3) 0.36003(15) 0.0281(6) Uani 1 1 d . . . H9 H 0.2676 0.2039 0.4018 0.034 Uiso 1 1 calc R . . C7 C 0.25827(14) -0.0340(3) 0.25297(14) 0.0254(5) Uani 1 1 d . . . H7 H 0.2252 -0.0881 0.2213 0.030 Uiso 1 1 calc R . . C3 C 0.36532(14) -0.3477(3) 0.08057(15) 0.0270(5) Uani 1 1 d . . . H3A H 0.3398 -0.4186 0.0493 0.032 Uiso 1 1 calc R . . C2 C 0.44093(14) -0.3382(3) 0.07642(15) 0.0271(5) Uani 1 1 d . . . H2 H 0.4671 -0.4041 0.0430 0.032 Uiso 1 1 calc R . . C10 C 0.35777(13) 0.1304(3) 0.34182(14) 0.0243(5) Uani 1 1 d . . . C8 C 0.23370(14) 0.0596(3) 0.31463(15) 0.0285(6) Uani 1 1 d . . . H8 H 0.1837 0.0668 0.3253 0.034 Uiso 1 1 calc R . . C1 C 0.47730(14) -0.2289(3) 0.12282(14) 0.0239(5) Uani 1 1 d . . . H1 H 0.5280 -0.2201 0.1183 0.029 Uiso 1 1 calc R . . C4 C 0.32803(14) -0.2498(3) 0.13217(14) 0.0254(5) Uani 1 1 d . . . H4 H 0.2771 -0.2531 0.1355 0.030 Uiso 1 1 calc R . . C23 C 0.47059(14) 0.3832(3) 0.28158(17) 0.0308(6) Uani 1 1 d . . . H23A H 0.4737 0.4791 0.3121 0.037 Uiso 1 1 calc R . . H23B H 0.4224 0.3787 0.2574 0.037 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0150(3) 0.0235(3) 0.0228(3) 0.000 -0.00177(19) 0.000 Cl1 0.0184(3) 0.0309(3) 0.0242(3) -0.0032(2) -0.0019(2) 0.0033(2) O3 0.0258(10) 0.0485(12) 0.0416(11) -0.0129(10) -0.0023(8) -0.0072(9) O4 0.0286(10) 0.0390(11) 0.0331(10) 0.0008(9) 0.0005(8) 0.0147(9) N2 0.0185(10) 0.0244(11) 0.0195(10) -0.0008(8) -0.0003(8) 0.0018(8) O6 0.0349(11) 0.0362(11) 0.0279(10) 0.0043(8) -0.0007(8) 0.0095(9) O1 0.0229(9) 0.0443(11) 0.0242(9) -0.0063(8) -0.0016(7) 0.0021(8) N3 0.0214(11) 0.0330(12) 0.0270(11) -0.0033(9) -0.0098(8) 0.0011(9) N1 0.0176(10) 0.0240(11) 0.0206(10) 0.0016(8) -0.0003(8) 0.0021(8) C6 0.0203(12) 0.0203(12) 0.0225(12) 0.0036(9) -0.0005(9) -0.0012(9) C5 0.0205(12) 0.0236(12) 0.0198(12) 0.0036(10) -0.0008(9) 0.0003(10) C11 0.0263(13) 0.0354(15) 0.0252(13) -0.0070(11) -0.0049(10) 0.0069(11) C9 0.0297(14) 0.0298(14) 0.0248(13) 0.0007(11) 0.0061(10) 0.0061(11) C7 0.0192(12) 0.0271(13) 0.0299(13) 0.0013(10) 0.0010(10) -0.0027(10) C3 0.0309(14) 0.0263(13) 0.0238(13) -0.0007(10) -0.0033(10) -0.0036(11) C2 0.0306(14) 0.0285(13) 0.0221(12) -0.0021(10) 0.0006(10) 0.0051(11) C10 0.0252(13) 0.0266(13) 0.0211(12) 0.0021(10) -0.0019(9) 0.0051(10) C8 0.0200(13) 0.0306(14) 0.0350(14) 0.0024(11) 0.0076(10) 0.0020(10) C1 0.0194(12) 0.0297(14) 0.0226(12) 0.0019(10) 0.0031(9) 0.0033(10) C4 0.0223(13) 0.0286(13) 0.0252(13) 0.0002(10) 0.0000(10) -0.0031(11) C23 0.0258(13) 0.0257(14) 0.0409(15) -0.0039(12) -0.0118(11) 0.0015(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 N2 2.229(2) 4_655 ? Mn1 N2 2.229(2) . ? Mn1 N1 2.231(2) . ? Mn1 N1 2.231(2) 4_655 ? Mn1 N3 2.299(2) . ? Mn1 N3 2.299(2) 4_655 ? Cl1 O3 1.435(2) . ? Cl1 O4 1.4425(19) . ? Cl1 O6 1.448(2) . ? Cl1 O1 1.4585(19) . ? N2 C10 1.340(3) . ? N2 C6 1.349(3) . ? N3 C11 1.475(3) . ? N3 C23 1.480(3) . ? N3 H3 0.9100 . ? N1 C1 1.339(3) . ? N1 C5 1.356(3) . ? C6 C7 1.393(3) . ? C6 C5 1.492(3) . ? C5 C4 1.389(3) . ? C11 C10 1.516(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C9 C8 1.382(4) . ? C9 C10 1.393(4) . ? C9 H9 0.9300 . ? C7 C8 1.391(4) . ? C7 H7 0.9300 . ? C3 C2 1.382(4) . ? C3 C4 1.388(4) . ? C3 H3A 0.9300 . ? C2 C1 1.388(4) . ? C2 H2 0.9300 . ? C8 H8 0.9300 . ? C1 H1 0.9300 . ? C4 H4 0.9300 . ? C23 C23 1.517(6) 4_655 ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Mn1 N2 179.77(11) 4_655 . ? N2 Mn1 N1 107.80(7) 4_655 . ? N2 Mn1 N1 72.04(7) . . ? N2 Mn1 N1 72.04(7) 4_655 4_655 ? N2 Mn1 N1 107.80(7) . 4_655 ? N1 Mn1 N1 96.94(11) . 4_655 ? N2 Mn1 N3 107.88(8) 4_655 . ? N2 Mn1 N3 72.31(7) . . ? N1 Mn1 N3 143.04(7) . . ? N1 Mn1 N3 102.87(8) 4_655 . ? N2 Mn1 N3 72.31(7) 4_655 4_655 ? N2 Mn1 N3 107.88(8) . 4_655 ? N1 Mn1 N3 102.87(8) . 4_655 ? N1 Mn1 N3 143.04(7) 4_655 4_655 ? N3 Mn1 N3 79.19(12) . 4_655 ? O3 Cl1 O4 110.54(13) . . ? O3 Cl1 O6 109.64(12) . . ? O4 Cl1 O6 109.28(11) . . ? O3 Cl1 O1 109.71(11) . . ? O4 Cl1 O1 108.61(11) . . ? O6 Cl1 O1 109.04(12) . . ? C10 N2 C6 120.2(2) . . ? C10 N2 Mn1 120.25(16) . . ? C6 N2 Mn1 119.14(16) . . ? C11 N3 C23 113.1(2) . . ? C11 N3 Mn1 111.25(16) . . ? C23 N3 Mn1 104.93(16) . . ? C11 N3 H3 109.1 . . ? C23 N3 H3 109.1 . . ? Mn1 N3 H3 109.1 . . ? C1 N1 C5 118.4(2) . . ? C1 N1 Mn1 122.90(16) . . ? C5 N1 Mn1 118.74(16) . . ? N2 C6 C7 121.1(2) . . ? N2 C6 C5 114.5(2) . . ? C7 C6 C5 124.4(2) . . ? N1 C5 C4 122.1(2) . . ? N1 C5 C6 114.9(2) . . ? C4 C5 C6 123.0(2) . . ? N3 C11 C10 110.2(2) . . ? N3 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? N3 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? C8 C9 C10 118.5(2) . . ? C8 C9 H9 120.8 . . ? C10 C9 H9 120.8 . . ? C8 C7 C6 118.4(2) . . ? C8 C7 H7 120.8 . . ? C6 C7 H7 120.8 . . ? C2 C3 C4 119.0(2) . . ? C2 C3 H3A 120.5 . . ? C4 C3 H3A 120.5 . . ? C3 C2 C1 119.1(2) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? N2 C10 C9 121.6(2) . . ? N2 C10 C11 114.7(2) . . ? C9 C10 C11 123.7(2) . . ? C9 C8 C7 120.1(2) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? N1 C1 C2 122.5(2) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C5 C4 C3 118.9(2) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? N3 C23 C23 109.51(18) . 4_655 ? N3 C23 H23A 109.8 . . ? C23 C23 H23A 109.8 4_655 . ? N3 C23 H23B 109.8 . . ? C23 C23 H23B 109.8 4_655 . ? H23A C23 H23B 108.2 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.304 _refine_diff_density_min -0.450 _refine_diff_density_rms 0.069 #===END data_nh13 _database_code_depnum_ccdc_archive 'CCDC 821597' #TrackingRef '- Combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H32 Cl2 Mn N8 O8' _chemical_formula_weight 746.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.842(5) _cell_length_b 9.232(2) _cell_length_c 15.816(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.422(11) _cell_angle_gamma 90.00 _cell_volume 3244.1(12) _cell_formula_units_Z 4 _cell_measurement_temperature 89(2) _cell_measurement_reflns_used 5922 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 29.19 _exptl_crystal_description Block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.37 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1540 _exptl_absorpt_coefficient_mu 0.635 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.867477 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 89(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa ApexII area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28974 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 29.49 _reflns_number_total 4371 _reflns_number_gt 3867 _reflns_threshold_expression >2\s(I) _computing_data_collection 'ApexII (Bruker, 2004)' _computing_cell_refinement 'ApexII and SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'WinGX (Farrugia, 1999)' _computing_publication_material WinGX _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0670P)^2^+5.3940P] 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 4371 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1343 _refine_ls_wR_factor_gt 0.1278 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 Mn1 Mn 0.5000 0.20722(4) 0.2500 0.02583(13) Uani 1 2 d S . . Cl2 Cl 0.36230(2) 0.53597(6) 0.96564(3) 0.03187(14) Uani 1 1 d . . . C33 C 0.24624(10) 0.6107(3) 0.17272(15) 0.0365(5) Uani 1 1 d . . . N1 N 0.51625(7) 0.03223(19) 0.15549(11) 0.0269(4) Uani 1 1 d . B . N2 N 0.41390(8) 0.1586(2) 0.16074(12) 0.0313(4) Uani 1 1 d . B . O8 O 0.33364(9) 0.4432(3) 0.89818(19) 0.0762(8) Uani 1 1 d . C . N9 N 0.21864(10) 0.5084(2) 0.17081(15) 0.0432(5) Uani 1 1 d . . . C1 C 0.56961(9) -0.0290(3) 0.15572(14) 0.0332(5) Uani 1 1 d . . . H1 H 0.6041 0.0106 0.1914 0.040 Uiso 1 1 calc R B . C3 C 0.52466(11) -0.2087(3) 0.05355(15) 0.0361(5) Uani 1 1 d . . . H3 H 0.5274 -0.2901 0.0200 0.043 Uiso 1 1 calc R B . C24 C 0.5000 0.5842(3) 0.2500 0.0348(6) Uani 1 2 d S . . H24A H 0.4984 0.6480 0.2008 0.042 Uiso 0.50 1 calc PR A 1 H24B H 0.5016 0.6480 0.2992 0.042 Uiso 0.50 1 calc PR A 1 C4 C 0.46892(10) -0.1465(2) 0.05194(14) 0.0309(4) Uani 1 1 d . B . H4 H 0.4340 -0.1851 0.0171 0.037 Uiso 1 1 calc R . . C6 C 0.40876(8) 0.0488(2) 0.10456(12) 0.0242(4) Uani 1 1 d . . . C8 C 0.30283(9) 0.0891(3) 0.06019(14) 0.0340(5) Uani 1 1 d . . . H8 H 0.2653 0.0660 0.0254 0.041 Uiso 1 1 calc R B . C2 C 0.57573(10) -0.1482(3) 0.10544(15) 0.0371(5) Uani 1 1 d . B . H2 H 0.6135 -0.1868 0.1066 0.045 Uiso 1 1 calc R . . C5 C 0.46635(9) -0.0258(2) 0.10324(12) 0.0250(4) Uani 1 1 d . B . C9 C 0.30809(10) 0.1997(3) 0.11883(16) 0.0393(5) Uani 1 1 d . B . H9 H 0.2745 0.2516 0.1253 0.047 Uiso 1 1 calc R . . C7 C 0.35322(9) 0.0111(3) 0.05232(14) 0.0324(4) Uani 1 1 d . B . H7 H 0.3498 -0.0649 0.0129 0.039 Uiso 1 1 calc R . . C10 C 0.36494(11) 0.2323(3) 0.16836(19) 0.0487(7) Uani 1 1 d . . . C22 C 0.28228(14) 0.7413(3) 0.1757(3) 0.0638(9) Uani 1 1 d . . . H22A H 0.3060 0.7556 0.2337 0.096 Uiso 1 1 calc R . . H22B H 0.2562 0.8231 0.1588 0.096 Uiso 1 1 calc R . . H22C H 0.3084 0.7315 0.1365 0.096 Uiso 1 1 calc R . . C11A C 0.37070(18) 0.3218(5) 0.2554(3) 0.0314(10) Uani 0.511(5) 1 d P B 1 H11A H 0.3424 0.4019 0.2460 0.038 Uiso 0.511(5) 1 calc PR B 1 H11B H 0.3621 0.2603 0.3007 0.038 Uiso 0.511(5) 1 calc PR B 1 N3A N 0.4363(5) 0.3797(16) 0.2825(7) 0.0193(14) Uani 0.511(5) 1 d P B 1 H3A H 0.4460 0.3980 0.3406 0.023 Uiso 0.511(5) 1 calc PR B 1 C23A C 0.4359(2) 0.5206(5) 0.2326(3) 0.0370(11) Uani 0.511(5) 1 d P B 1 H23A H 0.4091 0.5894 0.2506 0.044 Uiso 0.511(5) 1 calc PR B 1 H23B H 0.4212 0.5028 0.1708 0.044 Uiso 0.511(5) 1 calc PR B 1 C11B C 0.3823(2) 0.3799(5) 0.2106(3) 0.0333(11) Uani 0.489(5) 1 d P B 2 H11C H 0.3853 0.4498 0.1660 0.040 Uiso 0.489(5) 1 calc PR B 2 H11D H 0.3510 0.4124 0.2384 0.040 Uiso 0.489(5) 1 calc PR B 2 N3B N 0.4347(7) 0.374(2) 0.2696(9) 0.048(4) Uani 0.489(5) 1 d P B 2 H3B H 0.4226 0.3369 0.3160 0.057 Uiso 0.489(5) 1 calc PR B 2 C23B C 0.4619(2) 0.5175(5) 0.3075(3) 0.0344(12) Uani 0.489(5) 1 d P B 2 H23C H 0.4300 0.5840 0.3123 0.041 Uiso 0.489(5) 1 calc PR B 2 H23D H 0.4868 0.5012 0.3654 0.041 Uiso 0.489(5) 1 calc PR B 2 O2A O 0.42448(15) 0.5506(4) 0.9660(3) 0.0375(9) Uani 0.494(5) 1 d P C 1 O3A O 0.33434(17) 0.6680(5) 0.9675(4) 0.0676(18) Uani 0.494(5) 1 d P C 1 O4A O 0.3550(3) 0.4435(9) 1.0343(3) 0.117(4) Uani 0.494(5) 1 d P C 1 O2B O 0.42300(15) 0.5025(4) 1.0145(3) 0.0420(10) Uani 0.506(5) 1 d P C 2 O3B O 0.36645(16) 0.6679(4) 0.9138(2) 0.0434(10) Uani 0.506(5) 1 d P C 2 O4B O 0.32769(15) 0.5794(4) 1.0270(2) 0.0405(10) Uani 0.506(5) 1 d P C 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 Mn1 0.0216(2) 0.0214(2) 0.0302(2) 0.000 -0.00270(16) 0.000 Cl2 0.0271(3) 0.0337(3) 0.0371(3) -0.00322(19) 0.0122(2) -0.00292(18) C33 0.0281(10) 0.0392(13) 0.0410(12) -0.0046(9) 0.0055(9) 0.0064(9) N1 0.0217(8) 0.0353(9) 0.0242(7) 0.0005(6) 0.0063(6) -0.0017(6) N2 0.0229(8) 0.0275(9) 0.0378(9) -0.0046(7) -0.0043(7) 0.0046(7) O8 0.0405(11) 0.0772(15) 0.114(2) -0.0660(15) 0.0245(12) -0.0194(10) N9 0.0341(10) 0.0428(12) 0.0512(12) 0.0043(9) 0.0070(9) 0.0013(9) C1 0.0223(9) 0.0485(13) 0.0298(10) -0.0012(9) 0.0082(8) -0.0014(9) C3 0.0436(13) 0.0328(12) 0.0356(11) -0.0018(8) 0.0167(10) 0.0034(9) C24 0.0444(18) 0.0238(14) 0.0356(15) 0.000 0.0080(14) 0.000 C4 0.0319(10) 0.0319(11) 0.0298(9) -0.0020(8) 0.0089(8) -0.0051(8) C6 0.0221(9) 0.0282(10) 0.0221(8) 0.0029(7) 0.0048(7) -0.0047(7) C8 0.0209(9) 0.0470(13) 0.0322(10) 0.0015(9) 0.0022(8) -0.0056(9) C2 0.0296(11) 0.0484(14) 0.0366(11) 0.0018(10) 0.0142(9) 0.0070(9) C5 0.0237(9) 0.0289(10) 0.0236(8) 0.0006(7) 0.0078(7) -0.0036(7) C9 0.0241(10) 0.0483(14) 0.0407(12) -0.0033(10) -0.0020(9) 0.0085(9) C7 0.0242(9) 0.0429(12) 0.0297(10) -0.0068(9) 0.0053(8) -0.0080(9) C10 0.0303(12) 0.0462(14) 0.0576(16) -0.0206(12) -0.0142(11) 0.0166(11) C22 0.0417(15) 0.0404(15) 0.108(3) -0.0168(17) 0.0157(17) -0.0032(12) C11A 0.0239(19) 0.033(2) 0.037(2) -0.0044(18) 0.0062(17) 0.0062(16) N3A 0.021(3) 0.026(3) 0.0103(16) -0.0031(16) 0.0018(16) -0.001(2) C23A 0.039(2) 0.028(2) 0.041(2) 0.0006(17) 0.0039(19) 0.0075(18) C11B 0.026(2) 0.039(3) 0.032(2) -0.0025(19) 0.0006(18) 0.0103(18) N3B 0.049(5) 0.034(5) 0.055(8) -0.007(5) 0.004(5) 0.001(4) C23B 0.046(3) 0.024(2) 0.036(2) -0.0013(16) 0.013(2) 0.0053(18) O2A 0.0233(15) 0.039(2) 0.050(2) -0.0126(17) 0.0084(15) -0.0004(13) O3A 0.031(2) 0.057(3) 0.109(4) -0.043(3) 0.005(2) 0.0071(18) O4A 0.103(5) 0.180(8) 0.051(3) 0.059(4) -0.018(3) -0.092(5) O2B 0.0295(17) 0.041(2) 0.055(2) -0.0081(18) 0.0082(17) 0.0053(15) O3B 0.041(2) 0.046(2) 0.0435(19) 0.0000(15) 0.0097(15) -0.0029(15) O4B 0.0357(17) 0.046(2) 0.0430(19) -0.0109(16) 0.0165(15) 0.0027(15) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 N2 2.1848(18) 2_655 ? Mn1 N2 2.1849(18) . ? Mn1 N3B 2.219(18) 2_655 ? Mn1 N3B 2.219(18) . ? Mn1 N1 2.2890(17) . ? Mn1 N1 2.2890(17) 2_655 ? Mn1 N3A 2.294(13) 2_655 ? Mn1 N3A 2.294(13) . ? Cl2 O3A 1.380(4) . ? Cl2 O8 1.406(2) . ? Cl2 O4A 1.421(4) . ? Cl2 O2A 1.425(3) . ? Cl2 O4B 1.444(3) . ? Cl2 O2B 1.455(4) . ? Cl2 O3B 1.484(4) . ? C33 N9 1.132(3) . ? C33 C22 1.455(4) . ? N1 C1 1.343(3) . ? N1 C5 1.353(3) . ? N2 C6 1.335(3) . ? N2 C10 1.338(3) . ? C1 C2 1.384(3) . ? C1 H1 0.9300 . ? C3 C2 1.379(4) . ? C3 C4 1.392(3) . ? C3 H3 0.9300 . ? C24 C23B 1.527(5) 2_655 ? C24 C23B 1.527(5) . ? C24 C23A 1.542(5) 2_655 ? C24 C23A 1.542(5) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C4 C5 1.388(3) . ? C4 H4 0.9300 . ? C6 C7 1.388(3) . ? C6 C5 1.489(3) . ? C8 C9 1.365(3) . ? C8 C7 1.388(3) . ? C8 H8 0.9300 . ? C2 H2 0.9300 . ? C9 C10 1.385(3) . ? C9 H9 0.9300 . ? C7 H7 0.9300 . ? C10 C11B 1.529(5) . ? C10 C11A 1.585(5) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C11A N3A 1.554(12) . ? C11A H11A 0.9700 . ? C11A H11B 0.9700 . ? N3A C23A 1.521(14) . ? N3A H3A 0.9100 . ? C23A H23A 0.9700 . ? C23A H23B 0.9700 . ? C11B N3B 1.336(16) . ? C11B H11C 0.9700 . ? C11B H11D 0.9700 . ? N3B C23B 1.522(18) . ? N3B H3B 0.9100 . ? C23B H23C 0.9700 . ? C23B H23D 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Mn1 N2 156.30(10) 2_655 . ? N2 Mn1 N3B 72.5(4) 2_655 2_655 ? N2 Mn1 N3B 125.9(4) . 2_655 ? N2 Mn1 N3B 125.9(4) 2_655 . ? N2 Mn1 N3B 72.5(4) . . ? N3B Mn1 N3B 91.8(9) 2_655 . ? N2 Mn1 N1 91.08(7) 2_655 . ? N2 Mn1 N1 72.02(6) . . ? N3B Mn1 N1 100.6(5) 2_655 . ? N3B Mn1 N1 143.0(4) . . ? N2 Mn1 N1 72.02(6) 2_655 2_655 ? N2 Mn1 N1 91.08(7) . 2_655 ? N3B Mn1 N1 143.0(4) 2_655 2_655 ? N3B Mn1 N1 100.6(5) . 2_655 ? N1 Mn1 N1 90.22(9) . 2_655 ? N2 Mn1 N3A 76.4(3) 2_655 2_655 ? N2 Mn1 N3A 121.4(3) . 2_655 ? N3B Mn1 N3A 4.8(6) 2_655 2_655 ? N3B Mn1 N3A 91.7(2) . 2_655 ? N1 Mn1 N3A 97.8(3) . 2_655 ? N1 Mn1 N3A 147.5(3) 2_655 2_655 ? N2 Mn1 N3A 121.4(3) 2_655 . ? N2 Mn1 N3A 76.4(3) . . ? N3B Mn1 N3A 91.7(2) 2_655 . ? N3B Mn1 N3A 4.8(6) . . ? N1 Mn1 N3A 147.5(3) . . ? N1 Mn1 N3A 97.8(3) 2_655 . ? N3A Mn1 N3A 92.1(6) 2_655 . ? O3A Cl2 O8 114.7(2) . . ? O3A Cl2 O4A 112.2(5) . . ? O8 Cl2 O4A 95.6(3) . . ? O3A Cl2 O2A 112.5(3) . . ? O8 Cl2 O2A 110.41(17) . . ? O4A Cl2 O2A 110.3(3) . . ? O3A Cl2 O4B 54.0(3) . . ? O8 Cl2 O4B 116.66(17) . . ? O4A Cl2 O4B 58.3(4) . . ? O2A Cl2 O4B 132.2(2) . . ? O3A Cl2 O2B 124.4(2) . . ? O8 Cl2 O2B 119.47(18) . . ? O4A Cl2 O2B 74.5(3) . . ? O2A Cl2 O2B 36.14(19) . . ? O4B Cl2 O2B 107.7(2) . . ? O3A Cl2 O3B 51.4(3) . . ? O8 Cl2 O3B 99.1(2) . . ? O4A Cl2 O3B 161.7(4) . . ? O2A Cl2 O3B 74.5(2) . . ? O4B Cl2 O3B 105.0(2) . . ? O2B Cl2 O3B 107.0(2) . . ? N9 C33 C22 179.4(3) . . ? C1 N1 C5 118.06(18) . . ? C1 N1 Mn1 125.46(14) . . ? C5 N1 Mn1 115.89(13) . . ? C6 N2 C10 119.98(19) . . ? C6 N2 Mn1 120.85(13) . . ? C10 N2 Mn1 118.90(15) . . ? N1 C1 C2 123.1(2) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C2 C3 C4 119.2(2) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C23B C24 C23B 132.4(4) 2_655 . ? C23B C24 C23A 45.9(3) 2_655 2_655 ? C23B C24 C23A 112.9(3) . 2_655 ? C23B C24 C23A 112.9(3) 2_655 . ? C23B C24 C23A 45.9(3) . . ? C23A C24 C23A 135.2(4) 2_655 . ? C23B C24 H24A 71.8 2_655 . ? C23B C24 H24A 143.4 . . ? C23A C24 H24A 103.4 2_655 . ? C23A C24 H24A 103.4 . . ? C23B C24 H24B 143.4 2_655 . ? C23B C24 H24B 71.8 . . ? C23A C24 H24B 103.4 2_655 . ? C23A C24 H24B 103.4 . . ? H24A C24 H24B 105.2 . . ? C5 C4 C3 118.9(2) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? N2 C6 C7 120.88(19) . . ? N2 C6 C5 114.76(17) . . ? C7 C6 C5 124.35(18) . . ? C9 C8 C7 120.3(2) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C3 C2 C1 118.7(2) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? N1 C5 C4 122.05(18) . . ? N1 C5 C6 115.48(17) . . ? C4 C5 C6 122.47(18) . . ? C8 C9 C10 118.0(2) . . ? C8 C9 H9 121.0 . . ? C10 C9 H9 121.0 . . ? C8 C7 C6 118.6(2) . . ? C8 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? N2 C10 C9 122.1(2) . . ? N2 C10 C11B 110.8(3) . . ? C9 C10 C11B 123.7(2) . . ? N2 C10 C11A 116.2(2) . . ? C9 C10 C11A 118.9(2) . . ? C11B C10 C11A 36.4(2) . . ? C33 C22 H22A 109.5 . . ? C33 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C33 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N3A C11A C10 107.4(5) . . ? N3A C11A H11A 110.2 . . ? C10 C11A H11A 110.2 . . ? N3A C11A H11B 110.2 . . ? C10 C11A H11B 110.2 . . ? H11A C11A H11B 108.5 . . ? C23A N3A C11A 105.2(8) . . ? C23A N3A Mn1 113.9(5) . . ? C11A N3A Mn1 108.7(7) . . ? C23A N3A H3A 109.6 . . ? C11A N3A H3A 109.6 . . ? Mn1 N3A H3A 109.6 . . ? N3A C23A C24 110.0(5) . . ? N3A C23A H23A 109.7 . . ? C24 C23A H23A 109.7 . . ? N3A C23A H23B 109.7 . . ? C24 C23A H23B 109.7 . . ? H23A C23A H23B 108.2 . . ? N3B C11B C10 111.8(9) . . ? N3B C11B H11C 109.3 . . ? C10 C11B H11C 109.3 . . ? N3B C11B H11D 109.3 . . ? C10 C11B H11D 109.3 . . ? H11C C11B H11D 107.9 . . ? C11B N3B C23B 117.4(14) . . ? C11B N3B Mn1 116.8(9) . . ? C23B N3B Mn1 115.6(9) . . ? C11B N3B H3B 100.8 . . ? C23B N3B H3B 100.8 . . ? Mn1 N3B H3B 100.8 . . ? C24 C23B N3B 110.7(6) . . ? C24 C23B H23C 109.5 . . ? N3B C23B H23C 109.5 . . ? C24 C23B H23D 109.5 . . ? N3B C23B H23D 109.5 . . ? H23C C23B H23D 108.1 . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.554 _refine_diff_density_min -0.659 _refine_diff_density_rms 0.080 #===END data_nh5 _database_code_depnum_ccdc_archive 'CCDC 821598' #TrackingRef '- Combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H24 Cl2 N6 Ni O8' _chemical_formula_weight 654.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.290(4) _cell_length_b 13.499(3) _cell_length_c 11.949(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.331(9) _cell_angle_gamma 90.00 _cell_volume 2615.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 89(2) _cell_measurement_reflns_used 8727 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 28.71 _exptl_crystal_description block _exptl_crystal_colour gold _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.661 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 1.009 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.898310 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 89(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa ApexII area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22387 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 28.82 _reflns_number_total 3414 _reflns_number_gt 3006 _reflns_threshold_expression >2\s(I) _computing_data_collection 'ApexII (Bruker,2004)' _computing_cell_refinement 'Apex and SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'WinGX (Farrugia, 1999)' _computing_publication_material WinGX _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0302P)^2^+5.4303P] 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 3414 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0870 _refine_ls_wR_factor_gt 0.0828 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.0000 0.23289(2) 0.2500 0.01696(10) Uani 1 2 d S . . Cl2 Cl 0.17236(3) 0.16259(4) 0.67497(4) 0.02310(12) Uani 1 1 d . . . O3 O 0.24002(10) 0.11581(13) 0.76613(14) 0.0378(4) Uani 1 1 d . . . O4 O 0.20037(10) 0.21559(12) 0.59209(14) 0.0348(4) Uani 1 1 d . . . N2 N -0.07290(10) 0.22635(12) 0.34697(14) 0.0197(3) Uani 1 1 d . . . O6 O 0.11386(14) 0.09011(17) 0.61084(16) 0.0630(7) Uani 1 1 d . . . O7 O 0.13361(17) 0.22956(19) 0.73084(18) 0.0744(8) Uani 1 1 d . . . N1 N 0.05565(10) 0.33770(11) 0.38440(14) 0.0208(3) Uani 1 1 d . . . N3 N -0.07944(10) 0.11519(12) 0.15815(14) 0.0208(3) Uani 1 1 d . . . H9 H -0.0963 0.1268 0.0782 0.025 Uiso 1 1 calc R . . C10 C -0.05023(12) 0.27529(14) 0.45236(16) 0.0210(4) Uani 1 1 d . . . C11 C 0.02203(12) 0.34123(14) 0.47122(17) 0.0220(4) Uani 1 1 d . . . C12 C -0.13510(12) 0.16171(15) 0.31597(17) 0.0225(4) Uani 1 1 d . . . C13 C 0.05428(13) 0.40342(16) 0.56993(18) 0.0282(4) Uani 1 1 d . . . H13 H 0.0310 0.4048 0.6294 0.034 Uiso 1 1 calc R . . C14 C -0.02908(13) 0.02380(14) 0.18545(17) 0.0263(4) Uani 1 1 d . . . H14A H 0.0027 0.0191 0.1328 0.032 Uiso 1 1 calc R . . H14B H -0.0651 -0.0335 0.1714 0.032 Uiso 1 1 calc R . . C15 C 0.15466(14) 0.45951(15) 0.4897(2) 0.0307(5) Uani 1 1 d . . . H15 H 0.1992 0.4997 0.4935 0.037 Uiso 1 1 calc R . . C16 C -0.15243(12) 0.11318(15) 0.19571(17) 0.0243(4) Uani 1 1 d . . . H16A H -0.1690 0.0450 0.1996 0.029 Uiso 1 1 calc R . . H16B H -0.1978 0.1473 0.1366 0.029 Uiso 1 1 calc R . . C17 C -0.09213(14) 0.25976(16) 0.53071(18) 0.0280(4) Uani 1 1 d . . . H17 H -0.0767 0.2930 0.6034 0.034 Uiso 1 1 calc R . . C18 C 0.12101(13) 0.39513(14) 0.39422(18) 0.0254(4) Uani 1 1 d . . . H18 H 0.1446 0.3918 0.3352 0.030 Uiso 1 1 calc R . . C19 C -0.15760(14) 0.19356(18) 0.49837(19) 0.0317(5) Uani 1 1 d . . . H19 H -0.1868 0.1826 0.5495 0.038 Uiso 1 1 calc R . . C20 C -0.17981(13) 0.14368(17) 0.39051(19) 0.0295(5) Uani 1 1 d . . . H20 H -0.2236 0.0992 0.3685 0.035 Uiso 1 1 calc R . . C21 C 0.12100(14) 0.46280(15) 0.57828(19) 0.0317(5) Uani 1 1 d . . . H21 H 0.1430 0.5047 0.6434 0.038 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.01740(18) 0.01614(17) 0.01580(16) 0.000 0.00381(13) 0.000 Cl2 0.0237(2) 0.0253(2) 0.0189(2) 0.00286(16) 0.00562(17) 0.00071(18) O3 0.0291(8) 0.0422(9) 0.0355(8) 0.0174(7) 0.0027(7) 0.0067(7) O4 0.0317(9) 0.0374(9) 0.0340(8) 0.0128(7) 0.0098(7) -0.0049(7) N2 0.0201(8) 0.0209(8) 0.0171(7) 0.0011(6) 0.0051(6) 0.0024(6) O6 0.0726(14) 0.0677(14) 0.0316(9) 0.0116(9) -0.0035(9) -0.0456(12) O7 0.108(2) 0.0883(17) 0.0386(11) 0.0234(11) 0.0405(12) 0.0684(15) N1 0.0216(8) 0.0166(7) 0.0208(8) 0.0010(6) 0.0029(6) 0.0021(6) N3 0.0237(8) 0.0202(8) 0.0161(7) 0.0000(6) 0.0037(6) -0.0025(6) C10 0.0203(9) 0.0219(9) 0.0184(8) 0.0004(7) 0.0038(7) 0.0053(7) C11 0.0216(10) 0.0178(9) 0.0209(9) -0.0004(7) 0.0003(7) 0.0066(7) C12 0.0197(9) 0.0233(9) 0.0220(9) 0.0044(7) 0.0039(7) -0.0005(7) C13 0.0284(11) 0.0263(10) 0.0244(9) -0.0050(8) 0.0021(8) 0.0070(8) C14 0.0314(11) 0.0187(9) 0.0257(10) -0.0045(7) 0.0058(8) -0.0014(8) C15 0.0264(11) 0.0199(10) 0.0356(11) 0.0010(8) -0.0024(9) -0.0035(8) C16 0.0217(10) 0.0244(10) 0.0237(9) 0.0011(7) 0.0038(8) -0.0053(8) C17 0.0316(11) 0.0316(11) 0.0212(9) 0.0019(8) 0.0097(8) 0.0078(9) C18 0.0240(10) 0.0199(9) 0.0269(10) 0.0033(7) 0.0022(8) -0.0004(8) C19 0.0295(11) 0.0409(13) 0.0294(10) 0.0095(9) 0.0162(9) 0.0064(10) C20 0.0240(10) 0.0346(11) 0.0296(10) 0.0073(9) 0.0091(8) -0.0016(9) C21 0.0312(11) 0.0197(10) 0.0312(11) -0.0074(8) -0.0056(9) 0.0043(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N2 1.9884(17) . ? Ni1 N2 1.9884(17) 2 ? Ni1 N1 2.1054(16) . ? Ni1 N1 2.1054(16) 2 ? Ni1 N3 2.1373(16) . ? Ni1 N3 2.1373(16) 2 ? Cl2 O7 1.422(2) . ? Cl2 O6 1.4244(19) . ? Cl2 O4 1.4355(16) . ? Cl2 O3 1.4382(15) . ? N2 C12 1.333(3) . ? N2 C10 1.354(2) . ? N1 C18 1.341(3) . ? N1 C11 1.355(3) . ? N3 C16 1.479(3) . ? N3 C14 1.480(3) . ? N3 H9 0.9100 . ? C10 C17 1.384(3) . ? C10 C11 1.486(3) . ? C11 C13 1.396(3) . ? C12 C20 1.389(3) . ? C12 C16 1.512(3) . ? C13 C21 1.380(3) . ? C13 H13 0.9300 . ? C14 C14 1.521(4) 2 ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C21 1.374(3) . ? C15 C18 1.391(3) . ? C15 H15 0.9300 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C19 1.388(3) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.385(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ni1 N2 174.91(9) . 2 ? N2 Ni1 N1 78.44(7) . . ? N2 Ni1 N1 105.07(7) 2 . ? N2 Ni1 N1 105.08(7) . 2 ? N2 Ni1 N1 78.44(7) 2 2 ? N1 Ni1 N1 95.56(9) . 2 ? N2 Ni1 N3 80.90(7) . . ? N2 Ni1 N3 95.29(6) 2 . ? N1 Ni1 N3 158.92(6) . . ? N1 Ni1 N3 93.79(6) 2 . ? N2 Ni1 N3 95.29(6) . 2 ? N2 Ni1 N3 80.90(6) 2 2 ? N1 Ni1 N3 93.79(6) . 2 ? N1 Ni1 N3 158.92(6) 2 2 ? N3 Ni1 N3 83.96(9) . 2 ? O7 Cl2 O6 109.07(17) . . ? O7 Cl2 O4 109.51(13) . . ? O6 Cl2 O4 108.54(11) . . ? O7 Cl2 O3 108.39(12) . . ? O6 Cl2 O3 110.16(12) . . ? O4 Cl2 O3 111.15(10) . . ? C12 N2 C10 121.50(17) . . ? C12 N2 Ni1 118.72(13) . . ? C10 N2 Ni1 118.89(13) . . ? C18 N1 C11 119.03(17) . . ? C18 N1 Ni1 127.08(14) . . ? C11 N1 Ni1 113.81(13) . . ? C16 N3 C14 114.62(16) . . ? C16 N3 Ni1 108.76(12) . . ? C14 N3 Ni1 106.41(11) . . ? C16 N3 H9 109.0 . . ? C14 N3 H9 109.0 . . ? Ni1 N3 H9 109.0 . . ? N2 C10 C17 120.31(19) . . ? N2 C10 C11 112.94(17) . . ? C17 C10 C11 126.73(18) . . ? N1 C11 C13 121.08(19) . . ? N1 C11 C10 115.13(16) . . ? C13 C11 C10 123.79(19) . . ? N2 C12 C20 120.76(19) . . ? N2 C12 C16 114.96(17) . . ? C20 C12 C16 124.27(18) . . ? C21 C13 C11 119.3(2) . . ? C21 C13 H13 120.4 . . ? C11 C13 H13 120.4 . . ? N3 C14 C14 110.78(13) . 2 ? N3 C14 H14A 109.5 . . ? C14 C14 H14A 109.5 2 . ? N3 C14 H14B 109.5 . . ? C14 C14 H14B 109.5 2 . ? H14A C14 H14B 108.1 . . ? C21 C15 C18 118.9(2) . . ? C21 C15 H15 120.5 . . ? C18 C15 H15 120.5 . . ? N3 C16 C12 111.86(16) . . ? N3 C16 H16A 109.2 . . ? C12 C16 H16A 109.2 . . ? N3 C16 H16B 109.2 . . ? C12 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C10 C17 C19 118.50(19) . . ? C10 C17 H17 120.7 . . ? C19 C17 H17 120.7 . . ? N1 C18 C15 122.2(2) . . ? N1 C18 H18 118.9 . . ? C15 C18 H18 118.9 . . ? C20 C19 C17 120.5(2) . . ? C20 C19 H19 119.7 . . ? C17 C19 H19 119.7 . . ? C19 C20 C12 118.4(2) . . ? C19 C20 H20 120.8 . . ? C12 C20 H20 120.8 . . ? C15 C21 C13 119.52(19) . . ? C15 C21 H21 120.2 . . ? C13 C21 H21 120.2 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.572 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.070 #===END