Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Socety of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 # SUBMISSION DETAILS _publ_contact_author_name 'Prof. En-Qing Gao' _publ_contact_author_address ; Department of Chemistry, East China Normal University, Shanghai 200062, China. ; _publ_contact_author_email eqgao@chem.ecnu.edu.cn _publ_contact_author_phone 86-21-62233404 _publ_contact_author_fax 86-21-62233424 _publ_section_title ; Supramolecular architectures based on transition metal complexes with 1-(3-pyridyl)-2-(4'-pyrimidyl)ethene ; loop_ _publ_author_name 'En-Qing Gao' 'Zhen-Xia Chen' 'Na Liu' 'Yanqin Wang' 'Lin-Hong Weng' data_1 _database_code_depnum_ccdc_archive 'CCDC 662562' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 Cd Cl2 N6 O12' _chemical_formula_weight 749.79 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9913(11) _cell_length_b 8.2560(12) _cell_length_c 11.3311(16) _cell_angle_alpha 85.809(2) _cell_angle_beta 79.323(2) _cell_angle_gamma 76.193(2) _cell_volume 713.09(17) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2752 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 27.49 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.746 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 378 _exptl_absorpt_coefficient_mu 1.026 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7484 _exptl_absorpt_correction_T_max 0.8212 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ' sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4038 _diffrn_reflns_av_R_equivalents 0.0114 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2740 _reflns_number_gt 2556 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0319P)^2^+0.3045P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2740 _refine_ls_number_parameters 212 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0640 _refine_ls_wR_factor_gt 0.0623 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.5000 1.0000 0.0000 0.04098(10) Uani 1 2 d S . . C1 C 0.3158(3) 1.0394(3) 0.27693(19) 0.0369(5) Uani 1 1 d . . . H1A H 0.2514 1.1371 0.2460 0.044 Uiso 1 1 calc R . . C2 C 0.5221(3) 0.7932(3) 0.2447(2) 0.0408(5) Uani 1 1 d . . . H2A H 0.6000 0.7175 0.1921 0.049 Uiso 1 1 calc R . . C3 C 0.5037(3) 0.7559(3) 0.3660(2) 0.0438(5) Uani 1 1 d . . . H3A H 0.5702 0.6577 0.3946 0.053 Uiso 1 1 calc R . . C4 C 0.3864(3) 0.8650(3) 0.4448(2) 0.0407(5) Uani 1 1 d . . . H4A H 0.3740 0.8416 0.5271 0.049 Uiso 1 1 calc R . . C5 C 0.2867(3) 1.0101(3) 0.40057(18) 0.0340(5) Uani 1 1 d . . . C6 C 0.1564(3) 1.1335(3) 0.47663(19) 0.0381(5) Uani 1 1 d . . . H6A H 0.0838 1.2175 0.4382 0.046 Uiso 1 1 calc R . . C7 C 0.1334(3) 1.1353(3) 0.59566(19) 0.0377(5) Uani 1 1 d . . . H7A H 0.2034 1.0496 0.6345 0.045 Uiso 1 1 calc R . . C8 C 0.0066(3) 1.2614(3) 0.67040(19) 0.0363(5) Uani 1 1 d . . . C9 C -0.1220(3) 1.3826(3) 0.6269(2) 0.0439(5) Uani 1 1 d . . . H9A H -0.1335 1.3879 0.5464 0.053 Uiso 1 1 calc R . . C10 C -0.2320(3) 1.4946(3) 0.7071(2) 0.0498(6) Uani 1 1 d . . . H10A H -0.3210 1.5746 0.6799 0.060 Uiso 1 1 calc R . . C11 C -0.0894(4) 1.3737(3) 0.8550(2) 0.0538(7) Uani 1 1 d . . . H11A H -0.0765 1.3717 0.9350 0.065 Uiso 1 1 calc R . . N1 N 0.4318(2) 0.9346(2) 0.19979(16) 0.0385(4) Uani 1 1 d . . . N2 N -0.2163(3) 1.4931(3) 0.8221(2) 0.0527(5) Uani 1 1 d . . . N3 N 0.0219(3) 1.2561(3) 0.78718(17) 0.0459(5) Uani 1 1 d . . . O1 O 0.7949(3) 0.9400(3) 0.0217(2) 0.0633(6) Uani 1 1 d . . . H1WB H 0.870(5) 0.913(4) -0.030(3) 0.075(12) Uiso 1 1 d . . . H1WA H 0.827(5) 0.911(4) 0.082(3) 0.078(12) Uiso 1 1 d . . . O2 O 0.5237(3) 0.7229(2) -0.03613(17) 0.0531(5) Uani 1 1 d D . . H2WB H 0.611(3) 0.654(3) -0.071(3) 0.065(9) Uiso 1 1 d D . . H2WA H 0.440(3) 0.723(5) -0.079(2) 0.140(19) Uiso 1 1 d D . . O3 O 0.3417(3) 0.7758(3) 0.7435(2) 0.0792(7) Uani 1 1 d . . . O5 O 0.0460(3) 0.8104(3) 0.8140(2) 0.0856(7) Uani 1 1 d . . . O6 O 0.2432(4) 0.5716(3) 0.86614(19) 0.0874(8) Uani 1 1 d . . . O4 O 0.1841(3) 0.6146(3) 0.67043(19) 0.0756(6) Uani 1 1 d . . . Cl1 Cl 0.20196(8) 0.69154(7) 0.77385(5) 0.04309(15) 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 Cd1 0.03972(15) 0.05138(16) 0.02238(12) -0.00929(9) -0.00023(9) 0.00640(10) C1 0.0350(12) 0.0421(12) 0.0284(11) -0.0074(9) -0.0035(9) 0.0016(9) C2 0.0382(12) 0.0425(12) 0.0350(12) -0.0111(9) 0.0018(9) 0.0007(10) C3 0.0475(14) 0.0391(12) 0.0387(13) -0.0012(10) -0.0045(10) 0.0000(10) C4 0.0472(13) 0.0436(12) 0.0272(11) -0.0033(9) -0.0010(9) -0.0059(10) C5 0.0320(11) 0.0415(12) 0.0269(10) -0.0096(9) 0.0008(8) -0.0075(9) C6 0.0363(12) 0.0425(12) 0.0308(11) -0.0089(9) -0.0006(9) -0.0019(9) C7 0.0394(12) 0.0392(12) 0.0304(11) -0.0086(9) 0.0006(9) -0.0037(9) C8 0.0369(12) 0.0410(12) 0.0295(11) -0.0089(9) 0.0020(9) -0.0096(9) C9 0.0400(13) 0.0530(14) 0.0358(12) -0.0126(10) -0.0025(10) -0.0049(10) C10 0.0402(14) 0.0511(14) 0.0518(15) -0.0140(12) -0.0021(11) 0.0010(11) C11 0.0587(16) 0.0626(16) 0.0313(12) -0.0163(11) 0.0015(11) 0.0005(13) N1 0.0377(10) 0.0457(10) 0.0267(9) -0.0105(8) -0.0024(7) 0.0014(8) N2 0.0499(13) 0.0567(13) 0.0436(12) -0.0221(10) 0.0041(10) -0.0004(10) N3 0.0524(12) 0.0506(12) 0.0280(10) -0.0104(8) 0.0004(9) -0.0021(9) O1 0.0384(11) 0.1020(17) 0.0389(11) -0.0085(11) -0.0049(9) 0.0048(10) O2 0.0493(11) 0.0556(11) 0.0488(10) -0.0244(8) -0.0081(9) 0.0053(9) O3 0.0648(14) 0.1133(19) 0.0695(14) 0.0124(13) -0.0214(11) -0.0369(13) O5 0.0559(13) 0.1002(17) 0.0801(16) -0.0280(13) -0.0041(11) 0.0239(12) O6 0.129(2) 0.0684(13) 0.0445(12) 0.0131(10) -0.0111(13) 0.0086(14) O4 0.0955(17) 0.0814(15) 0.0511(12) -0.0206(10) -0.0223(12) -0.0097(12) Cl1 0.0435(3) 0.0481(3) 0.0304(3) -0.0038(2) -0.0051(2) 0.0033(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 N1 2.2844(18) . ? Cd1 N1 2.2844(18) 2_675 ? Cd1 O2 2.3104(18) 2_675 ? Cd1 O2 2.3104(18) . ? Cd1 O1 2.345(2) . ? Cd1 O1 2.345(2) 2_675 ? C1 N1 1.342(3) . ? C1 C5 1.390(3) . ? C1 H1A 0.9300 . ? C2 N1 1.337(3) . ? C2 C3 1.375(3) . ? C2 H2A 0.9300 . ? C3 C4 1.375(3) . ? C3 H3A 0.9300 . ? C4 C5 1.388(3) . ? C4 H4A 0.9300 . ? C5 C6 1.468(3) . ? C6 C7 1.328(3) . ? C6 H6A 0.9300 . ? C7 C8 1.461(3) . ? C7 H7A 0.9300 . ? C8 N3 1.348(3) . ? C8 C9 1.388(3) . ? C9 C10 1.376(3) . ? C9 H9A 0.9300 . ? C10 N2 1.331(3) . ? C10 H10A 0.9300 . ? C11 N2 1.323(3) . ? C11 N3 1.329(3) . ? C11 H11A 0.9300 . ? O1 H1WB 0.76(4) . ? O1 H1WA 0.77(4) . ? O2 H2WB 0.841(17) . ? O2 H2WA 0.895(16) . ? O3 Cl1 1.429(2) . ? O5 Cl1 1.412(2) . ? O6 Cl1 1.415(2) . ? O4 Cl1 1.418(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 N1 Cd1 N1 180.0 . 2_675 ? N1 Cd1 O2 92.58(7) . 2_675 ? N1 Cd1 O2 87.42(7) 2_675 2_675 ? N1 Cd1 O2 87.42(7) . . ? N1 Cd1 O2 92.58(7) 2_675 . ? O2 Cd1 O2 180.00(9) 2_675 . ? N1 Cd1 O1 88.14(8) . . ? N1 Cd1 O1 91.86(8) 2_675 . ? O2 Cd1 O1 89.73(8) 2_675 . ? O2 Cd1 O1 90.27(8) . . ? N1 Cd1 O1 91.86(8) . 2_675 ? N1 Cd1 O1 88.14(8) 2_675 2_675 ? O2 Cd1 O1 90.27(8) 2_675 2_675 ? O2 Cd1 O1 89.73(8) . 2_675 ? O1 Cd1 O1 180.0 . 2_675 ? N1 C1 C5 123.6(2) . . ? N1 C1 H1A 118.2 . . ? C5 C1 H1A 118.2 . . ? N1 C2 C3 122.3(2) . . ? N1 C2 H2A 118.9 . . ? C3 C2 H2A 118.9 . . ? C4 C3 C2 119.5(2) . . ? C4 C3 H3A 120.2 . . ? C2 C3 H3A 120.2 . . ? C3 C4 C5 119.5(2) . . ? C3 C4 H4A 120.2 . . ? C5 C4 H4A 120.2 . . ? C4 C5 C1 117.16(19) . . ? C4 C5 C6 123.9(2) . . ? C1 C5 C6 119.0(2) . . ? C7 C6 C5 125.5(2) . . ? C7 C6 H6A 117.2 . . ? C5 C6 H6A 117.2 . . ? C6 C7 C8 125.1(2) . . ? C6 C7 H7A 117.4 . . ? C8 C7 H7A 117.4 . . ? N3 C8 C9 120.4(2) . . ? N3 C8 C7 115.9(2) . . ? C9 C8 C7 123.7(2) . . ? C10 C9 C8 117.6(2) . . ? C10 C9 H9A 121.2 . . ? C8 C9 H9A 121.2 . . ? N2 C10 C9 122.7(2) . . ? N2 C10 H10A 118.6 . . ? C9 C10 H10A 118.6 . . ? N2 C11 N3 127.7(2) . . ? N2 C11 H11A 116.2 . . ? N3 C11 H11A 116.2 . . ? C2 N1 C1 117.92(19) . . ? C2 N1 Cd1 119.11(14) . . ? C1 N1 Cd1 122.67(15) . . ? C11 N2 C10 115.3(2) . . ? C11 N3 C8 116.3(2) . . ? Cd1 O1 H1WB 123(3) . . ? Cd1 O1 H1WA 123(3) . . ? H1WB O1 H1WA 109(4) . . ? Cd1 O2 H2WB 128(2) . . ? Cd1 O2 H2WA 106(3) . . ? H2WB O2 H2WA 103(2) . . ? O5 Cl1 O6 110.70(16) . . ? O5 Cl1 O4 109.51(15) . . ? O6 Cl1 O4 111.09(15) . . ? O5 Cl1 O3 108.47(16) . . ? O6 Cl1 O3 107.76(16) . . ? O4 Cl1 O3 109.25(15) . . ? 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 C2 C3 C4 1.3(4) . . . . ? C2 C3 C4 C5 0.8(4) . . . . ? C3 C4 C5 C1 -1.9(3) . . . . ? C3 C4 C5 C6 179.2(2) . . . . ? N1 C1 C5 C4 1.1(3) . . . . ? N1 C1 C5 C6 -180.0(2) . . . . ? C4 C5 C6 C7 9.7(4) . . . . ? C1 C5 C6 C7 -169.2(2) . . . . ? C5 C6 C7 C8 178.2(2) . . . . ? C6 C7 C8 N3 -170.0(2) . . . . ? C6 C7 C8 C9 9.2(4) . . . . ? N3 C8 C9 C10 -0.4(4) . . . . ? C7 C8 C9 C10 -179.5(2) . . . . ? C8 C9 C10 N2 1.8(4) . . . . ? C3 C2 N1 C1 -2.2(4) . . . . ? C3 C2 N1 Cd1 171.62(19) . . . . ? C5 C1 N1 C2 1.0(3) . . . . ? C5 C1 N1 Cd1 -172.62(17) . . . . ? N1 Cd1 N1 C2 -54(100) 2_675 . . . ? O2 Cd1 N1 C2 -137.77(18) 2_675 . . . ? O2 Cd1 N1 C2 42.23(18) . . . . ? O1 Cd1 N1 C2 -48.12(18) . . . . ? O1 Cd1 N1 C2 131.88(18) 2_675 . . . ? N1 Cd1 N1 C1 119(100) 2_675 . . . ? O2 Cd1 N1 C1 35.76(18) 2_675 . . . ? O2 Cd1 N1 C1 -144.24(18) . . . . ? O1 Cd1 N1 C1 125.40(19) . . . . ? O1 Cd1 N1 C1 -54.60(19) 2_675 . . . ? N3 C11 N2 C10 -0.4(5) . . . . ? C9 C10 N2 C11 -1.4(4) . . . . ? N2 C11 N3 C8 1.8(4) . . . . ? C9 C8 N3 C11 -1.3(4) . . . . ? C7 C8 N3 C11 177.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1WB O5 0.76(4) 2.13(4) 2.882(3) 168(4) 1_654 O1 H1WA N3 0.77(4) 2.27(4) 2.997(3) 158(4) 2_676 O2 H2WB N2 0.841(17) 1.969(19) 2.797(3) 168(3) 1_644 O2 H2WA O3 0.895(16) 2.269(17) 3.070(3) 149(3) 1_554 _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.311 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.052 # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 662563' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H28 Cl2 Mn N6 O13' _chemical_formula_weight 710.34 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0588(11) _cell_length_b 14.1614(19) _cell_length_c 14.2226(18) _cell_angle_alpha 103.129(3) _cell_angle_beta 93.499(2) _cell_angle_gamma 104.069(3) _cell_volume 1521.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 970 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 19.66 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 730 _exptl_absorpt_coefficient_mu 0.682 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8757 _exptl_absorpt_correction_T_max 0.9350 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8605 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0984 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5844 _reflns_number_gt 3538 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+7.5909P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5844 _refine_ls_number_parameters 429 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.1060 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1648 _refine_ls_wR_factor_gt 0.1469 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.048 _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 0.21624(15) 0.73732(8) 0.27024(9) 0.0452(3) Uani 1 1 d . . . C1 C 0.2441(10) 0.5752(5) 0.3865(6) 0.051(2) Uani 1 1 d . . . H1A H 0.2611 0.5425 0.3248 0.061 Uiso 1 1 calc R . . C2 C 0.2041(11) 0.7138(6) 0.4869(6) 0.059(2) Uani 1 1 d . . . H2A H 0.1921 0.7790 0.4978 0.071 Uiso 1 1 calc R . . C3 C 0.2049(12) 0.6709(6) 0.5650(6) 0.066(2) Uani 1 1 d . . . H3A H 0.1908 0.7060 0.6263 0.079 Uiso 1 1 calc R . . C4 C 0.2267(11) 0.5764(6) 0.5510(6) 0.058(2) Uani 1 1 d . . . H4A H 0.2283 0.5466 0.6029 0.070 Uiso 1 1 calc R . . C5 C 0.2464(10) 0.5255(5) 0.4591(6) 0.0477(19) Uani 1 1 d . . . C6 C 0.2725(10) 0.4240(5) 0.4372(6) 0.053(2) Uani 1 1 d . . . H6A H 0.3110 0.4021 0.3778 0.064 Uiso 1 1 calc R . . C7 C 0.2464(10) 0.3606(5) 0.4939(6) 0.052(2) Uani 1 1 d . . . H7A H 0.2141 0.3831 0.5549 0.063 Uiso 1 1 calc R . . C8 C 0.2644(10) 0.2593(5) 0.4678(6) 0.0480(19) Uani 1 1 d . . . C9 C 0.3448(10) 0.2215(6) 0.3893(6) 0.053(2) Uani 1 1 d . . . H9A H 0.3935 0.2618 0.3495 0.064 Uiso 1 1 calc R . . C10 C 0.3502(11) 0.1240(6) 0.3725(7) 0.061(2) Uani 1 1 d . . . H11A H 0.4046 0.0989 0.3204 0.073 Uiso 1 1 calc R . . C11 C 0.2072(11) 0.1041(6) 0.5001(6) 0.062(2) Uani 1 1 d . . . H10A H 0.1593 0.0630 0.5394 0.074 Uiso 1 1 calc R . . C12 C 0.1995(10) 0.9051(5) 0.1560(5) 0.049(2) Uani 1 1 d . . . H12A H 0.1585 0.9316 0.2131 0.059 Uiso 1 1 calc R . . C13 C 0.2869(10) 0.7778(6) 0.0623(6) 0.053(2) Uani 1 1 d . . . H13A H 0.3055 0.7141 0.0517 0.063 Uiso 1 1 calc R . . C14 C 0.3163(11) 0.8289(6) -0.0088(6) 0.057(2) Uani 1 1 d . . . H14A H 0.3589 0.8013 -0.0650 0.069 Uiso 1 1 calc R . . C15 C 0.2826(10) 0.9203(6) 0.0033(6) 0.055(2) Uani 1 1 d . . . H15A H 0.3007 0.9552 -0.0448 0.066 Uiso 1 1 calc R . . C16 C 0.2208(9) 0.9614(5) 0.0884(5) 0.0429(18) Uani 1 1 d . . . C17 C 0.1843(10) 1.0601(5) 0.1092(6) 0.052(2) Uani 1 1 d . . . H17A H 0.1415 1.0786 0.1679 0.063 Uiso 1 1 calc R . . C18 C 0.2038(10) 1.1261(5) 0.0561(6) 0.053(2) Uani 1 1 d . . . H18A H 0.2488 1.1093 -0.0022 0.064 Uiso 1 1 calc R . . C19 C 0.1627(9) 1.2219(5) 0.0790(6) 0.0453(18) Uani 1 1 d . . . C20 C 0.0860(10) 1.2563(6) 0.1597(6) 0.056(2) Uani 1 1 d . . . H20A H 0.0564 1.2174 0.2038 0.067 Uiso 1 1 calc R . . C21 C 0.0551(11) 1.3480(6) 0.1729(6) 0.062(2) Uani 1 1 d . . . H21A H 0.0018 1.3707 0.2266 0.074 Uiso 1 1 calc R . . C22 C 0.1693(12) 1.3685(6) 0.0373(6) 0.063(2) Uani 1 1 d . . . H22A H 0.2009 1.4082 -0.0059 0.076 Uiso 1 1 calc R . . N1 N 0.2194(8) 0.6670(4) 0.3979(4) 0.0485(16) Uani 1 1 d . . . N2 N 0.2823(9) 0.0624(5) 0.4264(6) 0.065(2) Uani 1 1 d . . . N3 N 0.1936(9) 0.1987(5) 0.5235(5) 0.0536(17) Uani 1 1 d . . . N4 N 0.2325(8) 0.8157(4) 0.1468(4) 0.0496(16) Uani 1 1 d . . . N5 N 0.0976(9) 1.4076(5) 0.1124(5) 0.0594(18) Uani 1 1 d . . . N6 N 0.2014(9) 1.2791(5) 0.0163(5) 0.0552(18) Uani 1 1 d . . . O1 O 0.4425(9) 0.6861(5) 0.2312(6) 0.082(2) Uani 1 1 d D . . H1WA H 0.508(12) 0.716(7) 0.199(7) 0.123 Uiso 1 1 d D . . H1WB H 0.456(13) 0.634(5) 0.243(8) 0.123 Uiso 1 1 d D . . O2 O -0.0202(7) 0.7776(5) 0.3071(4) 0.0586(15) Uani 1 1 d D . . H2WA H -0.106(8) 0.770(7) 0.265(4) 0.088 Uiso 1 1 d D . . H2WB H -0.054(10) 0.779(7) 0.361(3) 0.088 Uiso 1 1 d D . . O3 O 0.3653(8) 0.8798(4) 0.3688(5) 0.0628(16) Uani 1 1 d D . . H3WA H 0.324(10) 0.928(5) 0.392(6) 0.094 Uiso 1 1 d D . . H3WB H 0.471(4) 0.897(6) 0.373(7) 0.094 Uiso 1 1 d D . . O4 O 0.0537(8) 0.5989(4) 0.1736(4) 0.0594(15) Uani 1 1 d D . . H4WA H 0.085(10) 0.545(4) 0.159(6) 0.089 Uiso 1 1 d D . . H4WB H -0.043(6) 0.589(6) 0.193(7) 0.089 Uiso 1 1 d D . . O5 O 0.7288(8) 0.7817(4) 0.1720(4) 0.0605(15) Uani 1 1 d D . . H5WA H 0.731(12) 0.842(3) 0.188(6) 0.091 Uiso 1 1 d D . . H5WB H 0.755(12) 0.763(6) 0.115(3) 0.091 Uiso 1 1 d D . . Cl1 Cl 0.7638(3) 1.04868(17) 0.27622(17) 0.0646(6) Uani 1 1 d . . . O6 O 0.9207(15) 1.0984(10) 0.3179(9) 0.209(4) Uani 1 1 d . . . O7 O 0.6857(12) 1.0144(7) 0.3468(7) 0.153(3) Uani 1 1 d . . . O8 O 0.7994(15) 0.9872(7) 0.1979(9) 0.177(4) Uani 1 1 d . . . O9 O 0.6976(13) 1.1210(7) 0.2456(6) 0.135(2) Uani 1 1 d . . . Cl2 Cl 0.6098(3) 0.45179(17) 0.19219(17) 0.0630(6) Uani 1 1 d . . . O10 O 0.7588(11) 0.5140(6) 0.2499(5) 0.122(3) Uani 1 1 d . . . O11 O 0.6225(14) 0.4443(8) 0.0965(6) 0.171(2) Uani 1 1 d . . . O12 O 0.5826(14) 0.3577(6) 0.2101(8) 0.165(3) Uani 1 1 d . . . O13 O 0.4733(12) 0.4813(8) 0.2230(8) 0.170(3) 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 Mn1 0.0563(8) 0.0329(6) 0.0554(8) 0.0177(5) 0.0180(6) 0.0194(5) C1 0.071(6) 0.038(4) 0.045(5) 0.010(4) 0.013(4) 0.017(4) C2 0.076(6) 0.037(4) 0.063(6) 0.004(4) 0.012(5) 0.019(4) C3 0.103(7) 0.049(5) 0.049(5) 0.011(4) 0.022(5) 0.025(5) C4 0.082(6) 0.044(5) 0.053(5) 0.018(4) 0.010(5) 0.017(4) C5 0.057(5) 0.039(4) 0.051(5) 0.014(4) 0.012(4) 0.017(4) C6 0.075(6) 0.045(4) 0.048(5) 0.017(4) 0.019(4) 0.023(4) C7 0.069(6) 0.039(4) 0.052(5) 0.014(4) 0.015(4) 0.017(4) C8 0.058(5) 0.035(4) 0.055(5) 0.014(4) 0.009(4) 0.016(4) C9 0.060(5) 0.050(5) 0.059(5) 0.020(4) 0.019(4) 0.023(4) C10 0.065(6) 0.053(5) 0.074(6) 0.014(5) 0.018(5) 0.031(4) C11 0.077(6) 0.054(5) 0.060(6) 0.025(4) 0.009(5) 0.017(5) C12 0.067(5) 0.045(4) 0.048(5) 0.021(4) 0.024(4) 0.028(4) C13 0.063(5) 0.039(4) 0.058(5) 0.010(4) 0.010(4) 0.017(4) C14 0.077(6) 0.054(5) 0.047(5) 0.015(4) 0.019(4) 0.024(4) C15 0.069(6) 0.046(5) 0.057(5) 0.024(4) 0.019(4) 0.016(4) C16 0.051(5) 0.033(4) 0.045(5) 0.010(3) 0.010(4) 0.009(3) C17 0.070(6) 0.041(4) 0.056(5) 0.017(4) 0.016(4) 0.026(4) C18 0.074(6) 0.035(4) 0.058(5) 0.017(4) 0.018(4) 0.019(4) C19 0.049(5) 0.035(4) 0.055(5) 0.014(4) 0.007(4) 0.016(3) C20 0.068(6) 0.043(4) 0.062(6) 0.021(4) 0.016(4) 0.014(4) C21 0.068(6) 0.048(5) 0.068(6) 0.008(4) 0.017(5) 0.017(4) C22 0.088(7) 0.048(5) 0.062(6) 0.021(4) 0.018(5) 0.026(5) N1 0.064(4) 0.039(3) 0.049(4) 0.012(3) 0.010(3) 0.023(3) N2 0.077(5) 0.043(4) 0.080(5) 0.015(4) 0.010(4) 0.026(4) N3 0.073(5) 0.043(4) 0.056(4) 0.022(3) 0.017(4) 0.025(3) N4 0.070(5) 0.032(3) 0.048(4) 0.012(3) 0.018(3) 0.013(3) N5 0.072(5) 0.046(4) 0.065(5) 0.014(4) 0.012(4) 0.024(4) N6 0.083(5) 0.047(4) 0.047(4) 0.018(3) 0.015(4) 0.028(4) O1 0.081(5) 0.074(5) 0.129(6) 0.059(4) 0.049(4) 0.049(4) O2 0.065(4) 0.066(4) 0.058(4) 0.021(3) 0.022(3) 0.034(3) O3 0.067(4) 0.043(3) 0.078(4) 0.009(3) 0.008(4) 0.019(3) O4 0.066(4) 0.043(3) 0.070(4) 0.009(3) 0.021(3) 0.017(3) O5 0.077(4) 0.059(4) 0.054(4) 0.015(3) 0.021(3) 0.028(3) Cl1 0.0732(16) 0.0562(13) 0.0644(15) 0.0099(11) 0.0237(12) 0.0180(11) O6 0.134(9) 0.274(12) 0.174(9) 0.067(9) -0.023(8) -0.030(10) O7 0.156(8) 0.182(10) 0.173(9) 0.128(4) 0.074(7) 0.051(7) O8 0.230(11) 0.099(7) 0.199(11) 0.004(7) 0.042(9) 0.064(7) O9 0.195(10) 0.141(7) 0.121(7) 0.059(6) 0.052(6) 0.109(6) Cl2 0.0631(15) 0.0636(14) 0.0665(15) 0.0190(12) 0.0173(12) 0.0201(12) O10 0.119(6) 0.123(6) 0.082(5) 0.021(5) 0.009(5) -0.040(5) O11 0.201(10) 0.180(9) 0.087(6) 0.041(6) 0.005(7) -0.036(8) O12 0.205(11) 0.076(6) 0.201(10) 0.036(6) -0.006(8) 0.020(6) O13 0.117(8) 0.189(10) 0.222(12) 0.029(8) 0.072(7) 0.082(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O1 2.177(6) . ? Mn1 O2 2.178(5) . ? Mn1 O4 2.180(6) . ? Mn1 O3 2.193(6) . ? Mn1 N1 2.261(6) . ? Mn1 N4 2.275(6) . ? C1 N1 1.338(8) . ? C1 C5 1.377(10) . ? C1 H1A 0.9300 . ? C2 N1 1.318(9) . ? C2 C3 1.382(11) . ? C2 H2A 0.9300 . ? C3 C4 1.362(10) . ? C3 H3A 0.9300 . ? C4 C5 1.381(10) . ? C4 H4A 0.9300 . ? C5 C6 1.469(10) . ? C6 C7 1.325(10) . ? C6 H6A 0.9300 . ? C7 C8 1.443(9) . ? C7 H7A 0.9300 . ? C8 N3 1.348(9) . ? C8 C9 1.392(10) . ? C9 C10 1.359(10) . ? C9 H9A 0.9300 . ? C10 N2 1.330(10) . ? C10 H11A 0.9300 . ? C11 N2 1.336(10) . ? C11 N3 1.338(9) . ? C11 H10A 0.9300 . ? C12 N4 1.335(8) . ? C12 C16 1.376(9) . ? C12 H12A 0.9300 . ? C13 N4 1.345(9) . ? C13 C14 1.372(10) . ? C13 H13A 0.9300 . ? C14 C15 1.363(10) . ? C14 H14A 0.9300 . ? C15 C16 1.394(10) . ? C15 H15A 0.9300 . ? C16 C17 1.466(9) . ? C17 C18 1.316(10) . ? C17 H17A 0.9300 . ? C18 C19 1.446(9) . ? C18 H18A 0.9300 . ? C19 N6 1.337(9) . ? C19 C20 1.384(10) . ? C20 C21 1.356(10) . ? C20 H20A 0.9300 . ? C21 N5 1.341(10) . ? C21 H21A 0.9300 . ? C22 N5 1.320(10) . ? C22 N6 1.324(9) . ? C22 H22A 0.9300 . ? O1 H1WA 0.83(3) . ? O1 H1WB 0.82(3) . ? O2 H2WA 0.86(3) . ? O2 H2WB 0.83(3) . ? O3 H3WA 0.84(3) . ? O3 H3WB 0.82(3) . ? O4 H4WA 0.85(3) . ? O4 H4WB 0.83(3) . ? O5 H5WA 0.83(3) . ? O5 H5WB 0.85(3) . ? Cl1 O6 1.316(11) . ? Cl1 O7 1.338(8) . ? Cl1 O8 1.342(10) . ? Cl1 O9 1.401(8) . ? Cl2 O13 1.333(8) . ? Cl2 O11 1.354(9) . ? Cl2 O12 1.382(9) . ? Cl2 O10 1.389(7) . ? 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 Mn1 O2 176.0(3) . . ? O1 Mn1 O4 89.2(3) . . ? O2 Mn1 O4 87.3(2) . . ? O1 Mn1 O3 94.4(3) . . ? O2 Mn1 O3 89.2(2) . . ? O4 Mn1 O3 176.5(2) . . ? O1 Mn1 N1 87.9(2) . . ? O2 Mn1 N1 90.4(2) . . ? O4 Mn1 N1 92.7(2) . . ? O3 Mn1 N1 87.8(2) . . ? O1 Mn1 N4 90.1(2) . . ? O2 Mn1 N4 91.8(2) . . ? O4 Mn1 N4 91.0(2) . . ? O3 Mn1 N4 88.7(2) . . ? N1 Mn1 N4 175.8(2) . . ? N1 C1 C5 125.1(7) . . ? N1 C1 H1A 117.5 . . ? C5 C1 H1A 117.5 . . ? N1 C2 C3 123.2(7) . . ? N1 C2 H2A 118.4 . . ? C3 C2 H2A 118.4 . . ? C4 C3 C2 119.3(8) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C3 C4 C5 119.3(8) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? C1 C5 C4 116.7(7) . . ? C1 C5 C6 120.0(7) . . ? C4 C5 C6 123.3(7) . . ? C7 C6 C5 126.3(7) . . ? C7 C6 H6A 116.9 . . ? C5 C6 H6A 116.9 . . ? C6 C7 C8 124.8(7) . . ? C6 C7 H7A 117.6 . . ? C8 C7 H7A 117.6 . . ? N3 C8 C9 119.5(7) . . ? N3 C8 C7 116.0(7) . . ? C9 C8 C7 124.5(7) . . ? C10 C9 C8 118.1(7) . . ? C10 C9 H9A 121.0 . . ? C8 C9 H9A 121.0 . . ? N2 C10 C9 123.8(8) . . ? N2 C10 H11A 118.1 . . ? C9 C10 H11A 118.1 . . ? N2 C11 N3 126.9(8) . . ? N2 C11 H10A 116.5 . . ? N3 C11 H10A 116.5 . . ? N4 C12 C16 125.7(7) . . ? N4 C12 H12A 117.1 . . ? C16 C12 H12A 117.1 . . ? N4 C13 C14 122.9(7) . . ? N4 C13 H13A 118.5 . . ? C14 C13 H13A 118.5 . . ? C15 C14 C13 119.5(7) . . ? C15 C14 H14A 120.2 . . ? C13 C14 H14A 120.2 . . ? C14 C15 C16 119.7(7) . . ? C14 C15 H15A 120.2 . . ? C16 C15 H15A 120.2 . . ? C12 C16 C15 116.2(7) . . ? C12 C16 C17 120.1(7) . . ? C15 C16 C17 123.8(7) . . ? C18 C17 C16 128.8(7) . . ? C18 C17 H17A 115.6 . . ? C16 C17 H17A 115.6 . . ? C17 C18 C19 126.7(8) . . ? C17 C18 H18A 116.6 . . ? C19 C18 H18A 116.6 . . ? N6 C19 C20 119.3(7) . . ? N6 C19 C18 116.4(7) . . ? C20 C19 C18 124.3(7) . . ? C21 C20 C19 118.4(7) . . ? C21 C20 H20A 120.8 . . ? C19 C20 H20A 120.8 . . ? N5 C21 C20 123.1(8) . . ? N5 C21 H21A 118.4 . . ? C20 C21 H21A 118.4 . . ? N5 C22 N6 127.5(8) . . ? N5 C22 H22A 116.3 . . ? N6 C22 H22A 116.3 . . ? C2 N1 C1 116.3(7) . . ? C2 N1 Mn1 123.1(5) . . ? C1 N1 Mn1 120.6(5) . . ? C10 N2 C11 114.6(7) . . ? C11 N3 C8 117.1(7) . . ? C12 N4 C13 115.9(6) . . ? C12 N4 Mn1 122.1(5) . . ? C13 N4 Mn1 121.9(5) . . ? C22 N5 C21 114.3(7) . . ? C22 N6 C19 117.4(7) . . ? Mn1 O1 H1WA 118(7) . . ? Mn1 O1 H1WB 121(7) . . ? H1WA O1 H1WB 121(7) . . ? Mn1 O2 H2WA 123(6) . . ? Mn1 O2 H2WB 123(6) . . ? H2WA O2 H2WB 109(6) . . ? Mn1 O3 H3WA 124(6) . . ? Mn1 O3 H3WB 121(6) . . ? H3WA O3 H3WB 113(6) . . ? Mn1 O4 H4WA 123(6) . . ? Mn1 O4 H4WB 107(6) . . ? H4WA O4 H4WB 112(6) . . ? H5WA O5 H5WB 113(6) . . ? O6 Cl1 O7 104.3(7) . . ? O6 Cl1 O8 100.5(8) . . ? O7 Cl1 O8 122.3(7) . . ? O6 Cl1 O9 104.1(7) . . ? O7 Cl1 O9 114.3(6) . . ? O8 Cl1 O9 108.6(6) . . ? O13 Cl2 O11 114.5(7) . . ? O13 Cl2 O12 102.8(7) . . ? O11 Cl2 O12 109.6(7) . . ? O13 Cl2 O10 109.6(6) . . ? O11 Cl2 O10 111.6(5) . . ? O12 Cl2 O10 108.3(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 C2 C3 C4 1.6(14) . . . . ? C2 C3 C4 C5 -0.4(14) . . . . ? N1 C1 C5 C4 -2.1(13) . . . . ? N1 C1 C5 C6 179.2(7) . . . . ? C3 C4 C5 C1 0.6(12) . . . . ? C3 C4 C5 C6 179.3(8) . . . . ? C1 C5 C6 C7 -166.7(8) . . . . ? C4 C5 C6 C7 14.6(14) . . . . ? C5 C6 C7 C8 176.5(8) . . . . ? C6 C7 C8 N3 -164.5(8) . . . . ? C6 C7 C8 C9 13.9(14) . . . . ? N3 C8 C9 C10 -0.7(12) . . . . ? C7 C8 C9 C10 -179.1(8) . . . . ? C8 C9 C10 N2 0.4(13) . . . . ? N4 C13 C14 C15 -2.9(13) . . . . ? C13 C14 C15 C16 0.8(13) . . . . ? N4 C12 C16 C15 -0.1(12) . . . . ? N4 C12 C16 C17 -178.2(7) . . . . ? C14 C15 C16 C12 0.6(12) . . . . ? C14 C15 C16 C17 178.6(8) . . . . ? C12 C16 C17 C18 176.8(9) . . . . ? C15 C16 C17 C18 -1.1(14) . . . . ? C16 C17 C18 C19 178.7(8) . . . . ? C17 C18 C19 N6 176.8(8) . . . . ? C17 C18 C19 C20 -3.8(14) . . . . ? N6 C19 C20 C21 -0.9(12) . . . . ? C18 C19 C20 C21 179.7(8) . . . . ? C19 C20 C21 N5 -1.1(13) . . . . ? C3 C2 N1 C1 -2.9(12) . . . . ? C3 C2 N1 Mn1 179.6(7) . . . . ? C5 C1 N1 C2 3.2(12) . . . . ? C5 C1 N1 Mn1 -179.2(6) . . . . ? O1 Mn1 N1 C2 132.9(7) . . . . ? O2 Mn1 N1 C2 -50.8(6) . . . . ? O4 Mn1 N1 C2 -138.1(6) . . . . ? O3 Mn1 N1 C2 38.4(6) . . . . ? N4 Mn1 N1 C2 71(3) . . . . ? O1 Mn1 N1 C1 -44.5(6) . . . . ? O2 Mn1 N1 C1 131.9(6) . . . . ? O4 Mn1 N1 C1 44.6(6) . . . . ? O3 Mn1 N1 C1 -139.0(6) . . . . ? N4 Mn1 N1 C1 -107(3) . . . . ? C9 C10 N2 C11 -0.3(13) . . . . ? N3 C11 N2 C10 0.5(14) . . . . ? N2 C11 N3 C8 -0.8(13) . . . . ? C9 C8 N3 C11 0.9(12) . . . . ? C7 C8 N3 C11 179.4(7) . . . . ? C16 C12 N4 C13 -1.8(12) . . . . ? C16 C12 N4 Mn1 174.0(6) . . . . ? C14 C13 N4 C12 3.3(12) . . . . ? C14 C13 N4 Mn1 -172.5(6) . . . . ? O1 Mn1 N4 C12 -141.3(6) . . . . ? O2 Mn1 N4 C12 42.2(6) . . . . ? O4 Mn1 N4 C12 129.5(6) . . . . ? O3 Mn1 N4 C12 -47.0(6) . . . . ? N1 Mn1 N4 C12 -79(3) . . . . ? O1 Mn1 N4 C13 34.2(6) . . . . ? O2 Mn1 N4 C13 -142.3(6) . . . . ? O4 Mn1 N4 C13 -54.9(6) . . . . ? O3 Mn1 N4 C13 128.6(6) . . . . ? N1 Mn1 N4 C13 96(3) . . . . ? N6 C22 N5 C21 0.4(14) . . . . ? C20 C21 N5 C22 1.3(13) . . . . ? N5 C22 N6 C19 -2.3(14) . . . . ? C20 C19 N6 C22 2.4(12) . . . . ? C18 C19 N6 C22 -178.1(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1WA O5 0.83(3) 1.90(6) 2.665(9) 153(11) . O1 H1WB O13 0.82(3) 2.15(5) 2.947(12) 161(11) . O2 H2WA O5 0.86(3) 1.88(3) 2.723(9) 167(9) 1_455 O2 H2WB N3 0.83(3) 2.05(4) 2.854(8) 162(8) 2_566 O3 H3WA N2 0.84(3) 1.97(4) 2.784(8) 162(9) 1_565 O3 H3WB O7 0.82(3) 2.21(7) 2.894(11) 141(8) . O4 H4WA N5 0.85(3) 1.94(4) 2.767(8) 166(8) 1_545 O4 H4WB O10 0.83(3) 2.02(5) 2.791(9) 154(8) 1_455 O5 H5WA O8 0.83(3) 1.96(4) 2.759(11) 161(8) . O5 H5WB N6 0.85(3) 1.91(3) 2.758(8) 176(9) 2_675 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.803 _refine_diff_density_min -0.656 _refine_diff_density_rms 0.103 # Attachment '3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 662564' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H28 Cl2 Co N6 O13' _chemical_formula_weight 714.33 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 7.9676(10) _cell_length_b 13.9800(14) _cell_length_c 14.1474(16) _cell_angle_alpha 102.630(2) _cell_angle_beta 94.6380(10) _cell_angle_gamma 103.165(2) _cell_volume 1483.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 933 _cell_measurement_theta_min 2.392 _cell_measurement_theta_max 21.869 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.600 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 734 _exptl_absorpt_coefficient_mu 0.833 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8511 _exptl_absorpt_correction_T_max 0.9213 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 4.21 _diffrn_reflns_number 6910 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.1774 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5734 _reflns_number_gt 3294 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5734 _refine_ls_number_parameters 429 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.1447 _refine_ls_R_factor_gt 0.0630 _refine_ls_wR_factor_ref 0.1367 _refine_ls_wR_factor_gt 0.1219 _refine_ls_goodness_of_fit_ref 0.893 _refine_ls_restrained_S_all 0.892 _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 Co1 Co 0.21476(11) 0.73916(6) 0.27221(6) 0.0370(3) Uani 1 1 d . . . C1 C 0.2367(7) 0.5762(4) 0.3821(4) 0.0371(15) Uani 1 1 d . . . H1A H 0.2484 0.5412 0.3201 0.044 Uiso 1 1 calc R . . C2 C 0.2001(7) 0.7190(4) 0.4835(5) 0.0417(16) Uani 1 1 d . . . H2A H 0.1889 0.7851 0.4938 0.050 Uiso 1 1 calc R . . C3 C 0.2017(8) 0.6764(4) 0.5614(5) 0.0498(18) Uani 1 1 d . . . H3A H 0.1880 0.7122 0.6227 0.060 Uiso 1 1 calc R . . C4 C 0.2244(8) 0.5785(4) 0.5479(5) 0.0471(18) Uani 1 1 d . . . H4A H 0.2259 0.5480 0.6001 0.056 Uiso 1 1 calc R . . C5 C 0.2441(7) 0.5283(4) 0.4572(5) 0.0378(16) Uani 1 1 d . . . C6 C 0.2692(7) 0.4254(4) 0.4357(5) 0.0404(16) Uani 1 1 d . . . H6A H 0.3045 0.4019 0.3757 0.048 Uiso 1 1 calc R . . C7 C 0.2455(7) 0.3633(4) 0.4947(5) 0.0431(17) Uani 1 1 d . . . H7A H 0.2157 0.3874 0.5560 0.052 Uiso 1 1 calc R . . C8 C 0.2632(7) 0.2592(4) 0.4695(5) 0.0371(16) Uani 1 1 d . . . C9 C 0.3466(8) 0.2213(4) 0.3925(5) 0.0438(17) Uani 1 1 d . . . H9A H 0.3968 0.2620 0.3531 0.053 Uiso 1 1 calc R . . C10 C 0.3522(8) 0.1222(5) 0.3766(5) 0.0529(19) Uani 1 1 d . . . H11A H 0.4082 0.0962 0.3255 0.064 Uiso 1 1 calc R . . C11 C 0.2060(8) 0.1036(5) 0.5029(5) 0.0502(18) Uani 1 1 d . . . H10A H 0.1550 0.0619 0.5412 0.060 Uiso 1 1 calc R . . C12 C 0.1984(7) 0.9036(4) 0.1624(4) 0.0381(16) Uani 1 1 d . . . H12A H 0.1562 0.9311 0.2188 0.046 Uiso 1 1 calc R . . C13 C 0.2834(7) 0.7729(4) 0.0706(5) 0.0432(17) Uani 1 1 d . . . H13A H 0.3012 0.7082 0.0610 0.052 Uiso 1 1 calc R . . C14 C 0.3132(8) 0.8232(4) -0.0022(5) 0.0462(18) Uani 1 1 d . . . H14A H 0.3528 0.7937 -0.0587 0.055 Uiso 1 1 calc R . . C15 C 0.2831(7) 0.9191(4) 0.0105(5) 0.0441(17) Uani 1 1 d . . . H15A H 0.3035 0.9549 -0.0374 0.053 Uiso 1 1 calc R . . C16 C 0.2233(7) 0.9602(4) 0.0937(4) 0.0342(15) Uani 1 1 d . . . C17 C 0.1863(7) 1.0602(4) 0.1138(5) 0.0414(17) Uani 1 1 d . . . H17A H 0.1416 1.0793 0.1717 0.050 Uiso 1 1 calc R . . C18 C 0.2089(7) 1.1259(4) 0.0597(5) 0.0446(17) Uani 1 1 d . . . H18A H 0.2560 1.1083 0.0022 0.053 Uiso 1 1 calc R . . C19 C 0.1669(7) 1.2242(4) 0.0813(5) 0.0392(16) Uani 1 1 d . . . C20 C 0.0866(8) 1.2588(5) 0.1603(5) 0.0487(18) Uani 1 1 d . . . H20A H 0.0551 1.2195 0.2043 0.058 Uiso 1 1 calc R . . C21 C 0.0545(8) 1.3529(4) 0.1721(5) 0.0468(18) Uani 1 1 d . . . H21A H -0.0028 1.3754 0.2239 0.056 Uiso 1 1 calc R . . C22 C 0.1747(8) 1.3736(4) 0.0388(5) 0.0499(18) Uani 1 1 d . . . H22A H 0.2065 1.4143 -0.0040 0.060 Uiso 1 1 calc R . . N1 N 0.2138(6) 0.6704(3) 0.3927(4) 0.0379(13) Uani 1 1 d . . . N2 N 0.2812(7) 0.0608(4) 0.4309(4) 0.0525(16) Uani 1 1 d . . . N3 N 0.1945(6) 0.1992(4) 0.5271(4) 0.0455(14) Uani 1 1 d . . . N4 N 0.2302(6) 0.8120(3) 0.1541(4) 0.0377(13) Uani 1 1 d . . . N5 N 0.1007(7) 1.4126(4) 0.1138(4) 0.0500(15) Uani 1 1 d . . . N6 N 0.2083(6) 1.2834(4) 0.0181(4) 0.0456(15) Uani 1 1 d . . . O1 O 0.4410(6) 0.6920(4) 0.2394(4) 0.0698(16) Uani 1 1 d D . . H1WA H 0.520(7) 0.718(5) 0.209(5) 0.105 Uiso 1 1 d D . . H1WB H 0.476(8) 0.663(5) 0.278(4) 0.105 Uiso 1 1 d D . . O2 O -0.0125(5) 0.7825(3) 0.3063(3) 0.0450(12) Uani 1 1 d D . . H2WA H -0.093(6) 0.773(5) 0.259(3) 0.068 Uiso 1 1 d D . . H2WB H -0.055(7) 0.777(5) 0.357(3) 0.068 Uiso 1 1 d D . . O3 O 0.3628(6) 0.8748(3) 0.3681(4) 0.0489(12) Uani 1 1 d D . . H3WA H 0.329(7) 0.923(3) 0.396(4) 0.073 Uiso 1 1 d D . . H3WB H 0.458(5) 0.896(4) 0.347(5) 0.073 Uiso 1 1 d D . . O4 O 0.0585(5) 0.6068(3) 0.1775(3) 0.0451(12) Uani 1 1 d D . . H4WA H 0.085(7) 0.553(3) 0.154(4) 0.068 Uiso 1 1 d D . . H4WB H -0.045(4) 0.586(4) 0.186(5) 0.068 Uiso 1 1 d D . . O5 O 0.7220(6) 0.7803(3) 0.1695(4) 0.0525(13) Uani 1 1 d D . . H5WA H 0.724(9) 0.840(2) 0.175(5) 0.079 Uiso 1 1 d D . . H5WB H 0.753(8) 0.763(4) 0.115(3) 0.079 Uiso 1 1 d D . . Cl1 Cl 0.7603(3) 1.04925(13) 0.27051(14) 0.0534(5) Uani 1 1 d . . . O6 O 0.9152(9) 1.1008(6) 0.3215(6) 0.176(3) Uani 1 1 d . . . O7 O 0.6675(8) 0.9993(5) 0.3247(5) 0.1482(16) Uani 1 1 d . . . O8 O 0.8081(10) 0.9888(4) 0.1899(5) 0.150(2) Uani 1 1 d . . . O9 O 0.6853(7) 1.1198(4) 0.2387(4) 0.1017(15) Uani 1 1 d . . . Cl2 Cl 0.6165(3) 0.45607(15) 0.19589(15) 0.0570(5) Uani 1 1 d . . . O10 O 0.7704(7) 0.5188(4) 0.2532(4) 0.100(2) Uani 1 1 d . . . O11 O 0.6245(8) 0.4530(5) 0.1000(5) 0.1456(19) Uani 1 1 d . . . O12 O 0.5915(9) 0.3584(4) 0.2099(5) 0.153(3) Uani 1 1 d . . . O13 O 0.4783(7) 0.4865(5) 0.2280(5) 0.147(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 Co1 0.0438(6) 0.0244(5) 0.0476(6) 0.0117(4) 0.0137(4) 0.0130(4) C1 0.043(4) 0.029(4) 0.038(4) 0.005(3) 0.009(3) 0.010(3) C2 0.051(5) 0.028(4) 0.045(5) 0.003(3) 0.006(3) 0.013(3) C3 0.069(5) 0.039(4) 0.039(5) 0.002(4) 0.011(4) 0.015(4) C4 0.070(5) 0.036(4) 0.037(5) 0.015(3) 0.004(3) 0.012(4) C5 0.035(4) 0.033(4) 0.044(5) 0.009(3) 0.003(3) 0.006(3) C6 0.051(5) 0.033(4) 0.040(4) 0.008(3) 0.008(3) 0.016(3) C7 0.055(5) 0.035(4) 0.044(5) 0.008(3) 0.014(3) 0.018(3) C8 0.039(4) 0.031(4) 0.044(4) 0.012(3) 0.007(3) 0.012(3) C9 0.045(4) 0.041(4) 0.053(5) 0.021(4) 0.017(3) 0.015(3) C10 0.056(5) 0.047(4) 0.065(5) 0.013(4) 0.021(4) 0.026(4) C11 0.056(5) 0.039(4) 0.064(5) 0.024(4) 0.018(4) 0.015(4) C12 0.042(4) 0.029(4) 0.048(5) 0.012(3) 0.015(3) 0.011(3) C13 0.047(4) 0.027(4) 0.053(5) 0.003(3) 0.011(3) 0.011(3) C14 0.057(5) 0.042(4) 0.041(5) 0.007(4) 0.016(3) 0.017(3) C15 0.049(5) 0.040(4) 0.051(5) 0.020(4) 0.014(3) 0.015(3) C16 0.042(4) 0.026(3) 0.038(4) 0.007(3) 0.013(3) 0.012(3) C17 0.054(5) 0.031(4) 0.047(5) 0.014(3) 0.017(3) 0.017(3) C18 0.058(5) 0.027(4) 0.055(5) 0.012(3) 0.018(4) 0.017(3) C19 0.040(4) 0.034(4) 0.046(5) 0.012(3) 0.003(3) 0.011(3) C20 0.050(5) 0.040(4) 0.056(5) 0.016(4) 0.018(4) 0.006(3) C21 0.049(5) 0.031(4) 0.058(5) 0.003(4) 0.017(4) 0.011(3) C22 0.070(5) 0.032(4) 0.055(5) 0.019(4) 0.009(4) 0.018(4) N1 0.044(3) 0.026(3) 0.046(4) 0.007(3) 0.013(3) 0.013(2) N2 0.054(4) 0.037(3) 0.072(5) 0.016(3) 0.016(3) 0.018(3) N3 0.064(4) 0.033(3) 0.047(4) 0.015(3) 0.016(3) 0.018(3) N4 0.039(3) 0.024(3) 0.050(4) 0.009(3) 0.012(3) 0.006(2) N5 0.057(4) 0.034(3) 0.059(4) 0.007(3) 0.010(3) 0.015(3) N6 0.068(4) 0.036(3) 0.042(4) 0.017(3) 0.016(3) 0.021(3) O1 0.057(4) 0.075(4) 0.112(5) 0.060(3) 0.044(3) 0.038(3) O2 0.048(3) 0.052(3) 0.044(3) 0.017(3) 0.015(2) 0.024(3) O3 0.051(3) 0.032(3) 0.064(4) 0.011(3) 0.011(2) 0.012(2) O4 0.045(3) 0.027(3) 0.062(3) 0.005(2) 0.013(3) 0.010(2) O5 0.067(3) 0.045(3) 0.052(3) 0.013(3) 0.021(3) 0.021(3) Cl1 0.0607(14) 0.0473(11) 0.0565(13) 0.0120(10) 0.0200(10) 0.0186(10) O6 0.095(6) 0.228(9) 0.174(8) 0.037(7) -0.038(5) 0.008(6) O7 0.139(6) 0.185(7) 0.208(7) 0.156(3) 0.114(4) 0.079(4) O8 0.266(9) 0.077(4) 0.137(7) 0.022(4) 0.089(5) 0.085(4) O9 0.156(6) 0.100(4) 0.078(4) 0.033(4) 0.024(4) 0.076(4) Cl2 0.0557(14) 0.0596(13) 0.0615(14) 0.0193(11) 0.0202(11) 0.0174(11) O10 0.072(4) 0.116(5) 0.072(4) 0.011(4) 0.003(3) -0.042(4) O11 0.133(7) 0.158(7) 0.101(5) 0.045(5) -0.007(4) -0.058(5) O12 0.205(7) 0.057(4) 0.177(8) 0.020(5) -0.006(5) 0.013(4) O13 0.087(5) 0.138(6) 0.223(8) 0.013(5) 0.070(4) 0.057(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O4 2.090(4) . ? Co1 O2 2.096(4) . ? Co1 O3 2.104(5) . ? Co1 O1 2.108(4) . ? Co1 N1 2.132(5) . ? Co1 N4 2.137(5) . ? C1 N1 1.349(6) . ? C1 C5 1.377(7) . ? C1 H1A 0.9300 . ? C2 N1 1.341(7) . ? C2 C3 1.363(7) . ? C2 H2A 0.9300 . ? C3 C4 1.396(7) . ? C3 H3A 0.9300 . ? C4 C5 1.362(7) . ? C4 H4A 0.9300 . ? C5 C6 1.466(7) . ? C6 C7 1.325(7) . ? C6 H6A 0.9300 . ? C7 C8 1.463(7) . ? C7 H7A 0.9300 . ? C8 N3 1.353(6) . ? C8 C9 1.391(7) . ? C9 C10 1.366(7) . ? C9 H9A 0.9300 . ? C10 N2 1.335(7) . ? C10 H11A 0.9300 . ? C11 N2 1.323(7) . ? C11 N3 1.332(7) . ? C11 H10A 0.9300 . ? C12 N4 1.344(6) . ? C12 C16 1.380(7) . ? C12 H12A 0.9300 . ? C13 N4 1.333(6) . ? C13 C14 1.375(7) . ? C13 H13A 0.9300 . ? C14 C15 1.391(7) . ? C14 H14A 0.9300 . ? C15 C16 1.365(7) . ? C15 H15A 0.9300 . ? C16 C17 1.466(7) . ? C17 C18 1.310(7) . ? C17 H17A 0.9300 . ? C18 C19 1.463(7) . ? C18 H18A 0.9300 . ? C19 N6 1.357(6) . ? C19 C20 1.382(7) . ? C20 C21 1.374(7) . ? C20 H20A 0.9300 . ? C21 N5 1.312(7) . ? C21 H21A 0.9300 . ? C22 N6 1.325(7) . ? C22 N5 1.328(7) . ? C22 H22A 0.9300 . ? O1 H1WA 0.85(3) . ? O1 H1WB 0.82(3) . ? O2 H2WA 0.85(3) . ? O2 H2WB 0.82(3) . ? O3 H3WA 0.82(3) . ? O3 H3WB 0.85(3) . ? O4 H4WA 0.84(3) . ? O4 H4WB 0.83(3) . ? O5 H5WA 0.81(3) . ? O5 H5WB 0.83(3) . ? Cl1 O7 1.308(5) . ? Cl1 O6 1.337(7) . ? Cl1 O9 1.396(5) . ? Cl1 O8 1.399(6) . ? Cl2 O13 1.346(5) . ? Cl2 O11 1.355(6) . ? Cl2 O12 1.395(6) . ? Cl2 O10 1.402(5) . ? 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 O4 Co1 O2 88.42(17) . . ? O4 Co1 O3 177.59(17) . . ? O2 Co1 O3 89.21(17) . . ? O4 Co1 O1 90.8(2) . . ? O2 Co1 O1 178.43(18) . . ? O3 Co1 O1 91.6(2) . . ? O4 Co1 N1 92.46(18) . . ? O2 Co1 N1 90.21(17) . . ? O3 Co1 N1 88.01(18) . . ? O1 Co1 N1 88.45(18) . . ? O4 Co1 N4 89.88(18) . . ? O2 Co1 N4 91.85(17) . . ? O3 Co1 N4 89.73(18) . . ? O1 Co1 N4 89.52(18) . . ? N1 Co1 N4 176.92(19) . . ? N1 C1 C5 124.4(6) . . ? N1 C1 H1A 117.8 . . ? C5 C1 H1A 117.8 . . ? N1 C2 C3 123.4(5) . . ? N1 C2 H2A 118.3 . . ? C3 C2 H2A 118.3 . . ? C2 C3 C4 119.1(6) . . ? C2 C3 H3A 120.5 . . ? C4 C3 H3A 120.5 . . ? C5 C4 C3 119.0(6) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? C4 C5 C1 118.1(5) . . ? C4 C5 C6 123.1(6) . . ? C1 C5 C6 118.9(6) . . ? C7 C6 C5 125.3(6) . . ? C7 C6 H6A 117.4 . . ? C5 C6 H6A 117.4 . . ? C6 C7 C8 124.2(6) . . ? C6 C7 H7A 117.9 . . ? C8 C7 H7A 117.9 . . ? N3 C8 C9 120.2(5) . . ? N3 C8 C7 116.0(5) . . ? C9 C8 C7 123.8(5) . . ? C10 C9 C8 117.7(6) . . ? C10 C9 H9A 121.2 . . ? C8 C9 H9A 121.2 . . ? N2 C10 C9 123.3(6) . . ? N2 C10 H11A 118.4 . . ? C9 C10 H11A 118.4 . . ? N2 C11 N3 127.8(6) . . ? N2 C11 H10A 116.1 . . ? N3 C11 H10A 116.1 . . ? N4 C12 C16 125.1(5) . . ? N4 C12 H12A 117.4 . . ? C16 C12 H12A 117.4 . . ? N4 C13 C14 123.5(5) . . ? N4 C13 H13A 118.2 . . ? C14 C13 H13A 118.2 . . ? C13 C14 C15 118.7(6) . . ? C13 C14 H14A 120.7 . . ? C15 C14 H14A 120.7 . . ? C16 C15 C14 119.5(6) . . ? C16 C15 H15A 120.3 . . ? C14 C15 H15A 120.3 . . ? C15 C16 C12 117.2(5) . . ? C15 C16 C17 123.7(5) . . ? C12 C16 C17 119.0(5) . . ? C18 C17 C16 127.6(6) . . ? C18 C17 H17A 116.2 . . ? C16 C17 H17A 116.2 . . ? C17 C18 C19 125.9(6) . . ? C17 C18 H18A 117.1 . . ? C19 C18 H18A 117.1 . . ? N6 C19 C20 119.0(5) . . ? N6 C19 C18 116.7(5) . . ? C20 C19 C18 124.2(6) . . ? C21 C20 C19 118.2(6) . . ? C21 C20 H20A 120.9 . . ? C19 C20 H20A 120.9 . . ? N5 C21 C20 123.3(6) . . ? N5 C21 H21A 118.4 . . ? C20 C21 H21A 118.4 . . ? N6 C22 N5 127.4(6) . . ? N6 C22 H22A 116.3 . . ? N5 C22 H22A 116.3 . . ? C2 N1 C1 116.1(5) . . ? C2 N1 Co1 122.7(4) . . ? C1 N1 Co1 121.1(4) . . ? C11 N2 C10 114.8(5) . . ? C11 N3 C8 116.2(5) . . ? C13 N4 C12 116.0(5) . . ? C13 N4 Co1 122.2(4) . . ? C12 N4 Co1 121.6(4) . . ? C21 N5 C22 115.0(5) . . ? C22 N6 C19 116.9(5) . . ? Co1 O1 H1WA 128(5) . . ? Co1 O1 H1WB 114(5) . . ? H1WA O1 H1WB 113(6) . . ? Co1 O2 H2WA 117(4) . . ? Co1 O2 H2WB 124(4) . . ? H2WA O2 H2WB 110(5) . . ? Co1 O3 H3WA 128(5) . . ? Co1 O3 H3WB 110(4) . . ? H3WA O3 H3WB 110(5) . . ? Co1 O4 H4WA 129(4) . . ? Co1 O4 H4WB 120(4) . . ? H4WA O4 H4WB 102(5) . . ? H5WA O5 H5WB 104(5) . . ? O7 Cl1 O6 109.7(5) . . ? O7 Cl1 O9 114.0(4) . . ? O6 Cl1 O9 106.7(4) . . ? O7 Cl1 O8 115.0(4) . . ? O6 Cl1 O8 101.8(5) . . ? O9 Cl1 O8 108.7(4) . . ? O13 Cl2 O11 113.1(5) . . ? O13 Cl2 O12 104.0(4) . . ? O11 Cl2 O12 109.5(4) . . ? O13 Cl2 O10 109.9(4) . . ? O11 Cl2 O10 110.4(3) . . ? O12 Cl2 O10 109.8(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 C2 C3 C4 2.2(10) . . . . ? C2 C3 C4 C5 0.0(9) . . . . ? C3 C4 C5 C1 -1.5(9) . . . . ? C3 C4 C5 C6 179.8(6) . . . . ? N1 C1 C5 C4 1.0(9) . . . . ? N1 C1 C5 C6 179.8(5) . . . . ? C4 C5 C6 C7 12.5(10) . . . . ? C1 C5 C6 C7 -166.2(6) . . . . ? C5 C6 C7 C8 176.9(6) . . . . ? C6 C7 C8 N3 -164.5(6) . . . . ? C6 C7 C8 C9 16.3(10) . . . . ? N3 C8 C9 C10 1.5(10) . . . . ? C7 C8 C9 C10 -179.4(6) . . . . ? C8 C9 C10 N2 0.4(11) . . . . ? N4 C13 C14 C15 -1.4(10) . . . . ? C13 C14 C15 C16 -0.7(10) . . . . ? C14 C15 C16 C12 1.0(9) . . . . ? C14 C15 C16 C17 -179.5(6) . . . . ? N4 C12 C16 C15 0.8(9) . . . . ? N4 C12 C16 C17 -178.7(5) . . . . ? C15 C16 C17 C18 -2.6(11) . . . . ? C12 C16 C17 C18 176.9(6) . . . . ? C16 C17 C18 C19 178.6(6) . . . . ? C17 C18 C19 N6 176.8(6) . . . . ? C17 C18 C19 C20 -4.1(11) . . . . ? N6 C19 C20 C21 -1.0(10) . . . . ? C18 C19 C20 C21 -180.0(6) . . . . ? C19 C20 C21 N5 -2.0(11) . . . . ? C3 C2 N1 C1 -2.6(9) . . . . ? C3 C2 N1 Co1 -179.1(5) . . . . ? C5 C1 N1 C2 0.9(8) . . . . ? C5 C1 N1 Co1 177.5(4) . . . . ? O4 Co1 N1 C2 -139.6(4) . . . . ? O2 Co1 N1 C2 -51.2(5) . . . . ? O3 Co1 N1 C2 38.0(4) . . . . ? O1 Co1 N1 C2 129.6(5) . . . . ? N4 Co1 N1 C2 81(4) . . . . ? O4 Co1 N1 C1 44.0(4) . . . . ? O2 Co1 N1 C1 132.5(4) . . . . ? O3 Co1 N1 C1 -138.3(4) . . . . ? O1 Co1 N1 C1 -46.7(5) . . . . ? N4 Co1 N1 C1 -96(4) . . . . ? N3 C11 N2 C10 -0.4(11) . . . . ? C9 C10 N2 C11 -0.9(10) . . . . ? N2 C11 N3 C8 2.2(11) . . . . ? C9 C8 N3 C11 -2.6(9) . . . . ? C7 C8 N3 C11 178.2(6) . . . . ? C14 C13 N4 C12 3.0(9) . . . . ? C14 C13 N4 Co1 -172.5(5) . . . . ? C16 C12 N4 C13 -2.8(9) . . . . ? C16 C12 N4 Co1 172.8(4) . . . . ? O4 Co1 N4 C13 -54.3(5) . . . . ? O2 Co1 N4 C13 -142.7(5) . . . . ? O3 Co1 N4 C13 128.1(5) . . . . ? O1 Co1 N4 C13 36.5(5) . . . . ? N1 Co1 N4 C13 85(4) . . . . ? O4 Co1 N4 C12 130.5(4) . . . . ? O2 Co1 N4 C12 42.1(5) . . . . ? O3 Co1 N4 C12 -47.1(4) . . . . ? O1 Co1 N4 C12 -138.7(5) . . . . ? N1 Co1 N4 C12 -90(4) . . . . ? C20 C21 N5 C22 3.0(10) . . . . ? N6 C22 N5 C21 -1.1(11) . . . . ? N5 C22 N6 C19 -1.7(10) . . . . ? C20 C19 N6 C22 2.7(9) . . . . ? C18 C19 N6 C22 -178.3(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1WA O5 0.85(3) 1.84(3) 2.673(6) 167(7) . O1 H1WB O13 0.82(3) 2.41(7) 2.926(7) 122(7) . O2 H2WA O5 0.85(3) 1.90(3) 2.739(7) 167(6) 1_455 O2 H2WB N3 0.82(3) 2.06(3) 2.860(6) 162(6) 2_566 O3 H3WA N2 0.82(3) 2.01(3) 2.797(6) 161(6) 1_565 O3 H3WB O7 0.85(3) 2.04(4) 2.843(7) 157(5) . O4 H4WA N5 0.84(3) 1.95(3) 2.773(6) 166(5) 1_545 O4 H4WB O10 0.83(3) 1.99(4) 2.760(6) 154(6) 1_455 O5 H5WA O8 0.81(3) 2.00(3) 2.782(7) 162(7) . O5 H5WB N6 0.83(3) 1.93(3) 2.753(6) 172(7) 2_675 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.746 _refine_diff_density_min -0.494 _refine_diff_density_rms 0.080 # Attachment '4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 662565' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H28 Cl2 N6 Ni O13' _chemical_formula_weight 714.11 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9455(6) _cell_length_b 13.9534(11) _cell_length_c 14.0967(11) _cell_angle_alpha 102.465(2) _cell_angle_beta 94.739(2) _cell_angle_gamma 102.729(2) _cell_volume 1474.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1167 _cell_measurement_theta_min 2.391 _cell_measurement_theta_max 19.803 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.914 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8384 _exptl_absorpt_correction_T_max 0.9142 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15615 _diffrn_reflns_av_R_equivalents 0.0785 _diffrn_reflns_av_sigmaI/netI 0.1098 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5784 _reflns_number_gt 3358 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+3.3520P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5784 _refine_ls_number_parameters 429 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.1176 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1799 _refine_ls_wR_factor_gt 0.1545 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.21578(11) 0.73993(6) 0.27400(6) 0.0317(3) Uani 1 1 d . . . C1 C 0.2364(9) 0.5779(5) 0.3822(5) 0.0381(16) Uani 1 1 d . . . H1A H 0.2471 0.5428 0.3198 0.046 Uiso 1 1 calc R . . C2 C 0.1992(9) 0.7201(5) 0.4826(5) 0.0384(16) Uani 1 1 d . . . H2A H 0.1858 0.7859 0.4926 0.046 Uiso 1 1 calc R . . C3 C 0.2024(10) 0.6771(5) 0.5610(5) 0.0468(19) Uani 1 1 d . . . H3A H 0.1895 0.7132 0.6225 0.056 Uiso 1 1 calc R . . C4 C 0.2247(10) 0.5810(5) 0.5489(5) 0.0458(19) Uani 1 1 d . . . H4A H 0.2267 0.5510 0.6017 0.055 Uiso 1 1 calc R . . C5 C 0.2443(8) 0.5290(5) 0.4562(5) 0.0363(16) Uani 1 1 d . . . C6 C 0.2688(9) 0.4255(5) 0.4360(5) 0.0393(17) Uani 1 1 d . . . H6A H 0.3039 0.4014 0.3759 0.047 Uiso 1 1 calc R . . C7 C 0.2458(9) 0.3640(5) 0.4945(5) 0.0431(18) Uani 1 1 d . . . H7A H 0.2156 0.3884 0.5559 0.052 Uiso 1 1 calc R . . C8 C 0.2639(9) 0.2594(5) 0.4707(5) 0.0366(16) Uani 1 1 d . . . C9 C 0.3459(9) 0.2211(5) 0.3926(5) 0.0398(17) Uani 1 1 d . . . H9A H 0.3959 0.2616 0.3528 0.048 Uiso 1 1 calc R . . C10 C 0.3495(9) 0.1218(6) 0.3771(6) 0.050(2) Uani 1 1 d . . . H11A H 0.4044 0.0952 0.3255 0.060 Uiso 1 1 calc R . . C11 C 0.2046(9) 0.1038(5) 0.5036(5) 0.0438(18) Uani 1 1 d . . . H10A H 0.1548 0.0624 0.5426 0.053 Uiso 1 1 calc R . . C12 C 0.1990(8) 0.9043(5) 0.1666(5) 0.0349(16) Uani 1 1 d . . . H12A H 0.1593 0.9325 0.2238 0.042 Uiso 1 1 calc R . . C13 C 0.2832(9) 0.7706(5) 0.0730(5) 0.0406(17) Uani 1 1 d . . . H13A H 0.3029 0.7062 0.0642 0.049 Uiso 1 1 calc R . . C14 C 0.3101(9) 0.8203(5) -0.0005(5) 0.0454(18) Uani 1 1 d . . . H14A H 0.3469 0.7897 -0.0578 0.054 Uiso 1 1 calc R . . C15 C 0.2820(9) 0.9166(5) 0.0112(5) 0.0409(17) Uani 1 1 d . . . H15A H 0.3023 0.9518 -0.0373 0.049 Uiso 1 1 calc R . . C16 C 0.2230(9) 0.9598(5) 0.0966(5) 0.0373(16) Uani 1 1 d . . . C17 C 0.1853(9) 1.0596(5) 0.1158(5) 0.0396(17) Uani 1 1 d . . . H17A H 0.1393 1.0787 0.1734 0.047 Uiso 1 1 calc R . . C18 C 0.2088(9) 1.1253(5) 0.0612(5) 0.0416(17) Uani 1 1 d . . . H18A H 0.2562 1.1075 0.0037 0.050 Uiso 1 1 calc R . . C19 C 0.1669(9) 1.2247(5) 0.0827(5) 0.0374(16) Uani 1 1 d . . . C20 C 0.0863(10) 1.2582(5) 0.1613(5) 0.0469(19) Uani 1 1 d . . . H20A H 0.0543 1.2181 0.2048 0.056 Uiso 1 1 calc R . . C21 C 0.0546(10) 1.3522(5) 0.1736(6) 0.051(2) Uani 1 1 d . . . H21A H -0.0034 1.3744 0.2255 0.062 Uiso 1 1 calc R . . C22 C 0.1769(10) 1.3745(5) 0.0408(6) 0.050(2) Uani 1 1 d . . . H22A H 0.2103 1.4154 -0.0018 0.060 Uiso 1 1 calc R . . N1 N 0.2147(7) 0.6713(4) 0.3916(4) 0.0354(13) Uani 1 1 d . . . N2 N 0.2796(8) 0.0609(4) 0.4311(5) 0.0469(16) Uani 1 1 d . . . N3 N 0.1923(7) 0.1995(4) 0.5271(4) 0.0399(14) Uani 1 1 d . . . N4 N 0.2297(7) 0.8108(4) 0.1567(4) 0.0376(14) Uani 1 1 d . . . N5 N 0.1024(8) 1.4134(4) 0.1154(5) 0.0513(17) Uani 1 1 d . . . N6 N 0.2091(8) 1.2836(4) 0.0203(4) 0.0459(16) Uani 1 1 d . . . O1 O 0.4438(7) 0.6962(4) 0.2463(5) 0.0598(16) Uani 1 1 d D . . H1WA H 0.537(7) 0.731(5) 0.232(6) 0.090 Uiso 1 1 d D . . H1WB H 0.443(11) 0.638(3) 0.221(6) 0.090 Uiso 1 1 d D . . O2 O -0.0095(6) 0.7824(4) 0.3060(4) 0.0419(12) Uani 1 1 d D . . H2WA H -0.089(7) 0.776(6) 0.259(4) 0.063 Uiso 1 1 d D . . H2WB H -0.050(9) 0.786(6) 0.358(3) 0.063 Uiso 1 1 d D . . O3 O 0.3612(7) 0.8736(3) 0.3706(4) 0.0469(13) Uani 1 1 d D . . H3WA H 0.327(9) 0.924(4) 0.392(6) 0.070 Uiso 1 1 d D . . H3WB H 0.460(6) 0.878(6) 0.356(6) 0.070 Uiso 1 1 d D . . O4 O 0.0625(7) 0.6100(3) 0.1777(4) 0.0434(12) Uani 1 1 d D . . H4WA H 0.098(9) 0.559(4) 0.150(5) 0.065 Uiso 1 1 d D . . H4WB H -0.035(6) 0.588(5) 0.194(6) 0.065 Uiso 1 1 d D . . O5 O 0.7216(7) 0.7796(4) 0.1689(4) 0.0483(13) Uani 1 1 d D . . H5WA H 0.719(11) 0.841(3) 0.174(5) 0.072 Uiso 1 1 d D . . H5WB H 0.751(11) 0.758(5) 0.114(3) 0.072 Uiso 1 1 d D . . Cl1 Cl 0.7585(3) 1.04862(14) 0.26910(14) 0.0497(5) Uani 1 1 d . . . O6 O 0.9112(12) 1.1006(8) 0.3249(7) 0.160(4) Uani 1 1 d . . . O7 O 0.6611(11) 0.9954(7) 0.3218(7) 0.1333(19) Uani 1 1 d . . . O8 O 0.8068(12) 0.9887(5) 0.1861(6) 0.123(2) Uani 1 1 d . . . O9 O 0.6808(10) 1.1196(5) 0.2372(5) 0.098(2) Uani 1 1 d . . . Cl2 Cl 0.6180(3) 0.45878(15) 0.19563(16) 0.0528(5) Uani 1 1 d . . . O10 O 0.7729(9) 0.5193(5) 0.2532(4) 0.095(2) Uani 1 1 d . . . O11 O 0.6278(11) 0.4529(6) 0.0992(6) 0.133(2) Uani 1 1 d . . . O12 O 0.5858(13) 0.3607(5) 0.2105(7) 0.140(3) Uani 1 1 d . . . O13 O 0.4812(11) 0.4909(7) 0.2295(7) 0.140(3) 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 Ni1 0.0377(5) 0.0227(4) 0.0401(5) 0.0120(4) 0.0120(4) 0.0116(4) C1 0.051(4) 0.031(4) 0.035(4) 0.009(3) 0.010(3) 0.013(3) C2 0.047(4) 0.027(3) 0.043(4) 0.006(3) 0.011(3) 0.013(3) C3 0.067(5) 0.035(4) 0.036(4) 0.004(3) 0.007(4) 0.011(4) C4 0.064(5) 0.039(4) 0.039(4) 0.015(3) 0.009(4) 0.015(4) C5 0.039(4) 0.023(3) 0.046(4) 0.007(3) 0.007(3) 0.006(3) C6 0.050(4) 0.033(4) 0.038(4) 0.009(3) 0.014(3) 0.014(3) C7 0.053(5) 0.030(4) 0.051(5) 0.013(3) 0.016(4) 0.014(3) C8 0.039(4) 0.030(4) 0.041(4) 0.009(3) 0.008(3) 0.009(3) C9 0.041(4) 0.034(4) 0.049(4) 0.016(3) 0.016(3) 0.010(3) C10 0.042(5) 0.048(5) 0.060(5) 0.007(4) 0.010(4) 0.016(4) C11 0.055(5) 0.031(4) 0.052(5) 0.022(4) 0.013(4) 0.011(3) C12 0.039(4) 0.031(4) 0.039(4) 0.014(3) 0.014(3) 0.008(3) C13 0.043(4) 0.031(4) 0.049(5) 0.009(3) 0.010(4) 0.010(3) C14 0.056(5) 0.050(4) 0.032(4) 0.005(3) 0.015(4) 0.020(4) C15 0.051(5) 0.036(4) 0.040(4) 0.016(3) 0.011(3) 0.013(3) C16 0.041(4) 0.029(4) 0.044(4) 0.012(3) 0.010(3) 0.009(3) C17 0.040(4) 0.036(4) 0.042(4) 0.008(3) 0.007(3) 0.009(3) C18 0.058(5) 0.037(4) 0.035(4) 0.014(3) 0.015(4) 0.015(4) C19 0.038(4) 0.033(4) 0.045(4) 0.015(3) 0.006(3) 0.011(3) C20 0.056(5) 0.041(4) 0.048(5) 0.017(4) 0.018(4) 0.013(4) C21 0.062(5) 0.039(4) 0.052(5) 0.005(4) 0.017(4) 0.015(4) C22 0.068(6) 0.035(4) 0.055(5) 0.021(4) 0.003(4) 0.017(4) N1 0.040(3) 0.026(3) 0.044(4) 0.013(3) 0.013(3) 0.010(2) N2 0.053(4) 0.030(3) 0.062(4) 0.010(3) 0.012(3) 0.015(3) N3 0.052(4) 0.033(3) 0.042(4) 0.015(3) 0.013(3) 0.017(3) N4 0.041(3) 0.028(3) 0.049(4) 0.017(3) 0.011(3) 0.009(3) N5 0.062(4) 0.034(3) 0.058(4) 0.006(3) 0.011(3) 0.017(3) N6 0.068(4) 0.037(3) 0.041(4) 0.016(3) 0.017(3) 0.020(3) O1 0.049(3) 0.052(3) 0.103(5) 0.039(4) 0.046(3) 0.031(3) O2 0.047(3) 0.049(3) 0.040(3) 0.016(3) 0.016(2) 0.023(3) O3 0.051(3) 0.026(3) 0.064(4) 0.010(2) 0.011(3) 0.012(2) O4 0.050(3) 0.028(3) 0.052(3) 0.007(2) 0.014(3) 0.008(2) O5 0.062(3) 0.043(3) 0.044(3) 0.011(3) 0.017(3) 0.017(3) Cl1 0.0540(12) 0.0461(11) 0.0493(12) 0.0097(9) 0.0158(10) 0.0114(9) O6 0.105(7) 0.184(10) 0.162(9) 0.020(8) -0.047(6) 0.018(7) O7 0.127(7) 0.148(8) 0.188(9) 0.125(3) 0.090(6) 0.056(5) O8 0.201(9) 0.082(5) 0.106(6) 0.014(4) 0.066(5) 0.069(5) O9 0.154(7) 0.087(5) 0.082(5) 0.039(4) 0.028(5) 0.064(5) Cl2 0.0515(12) 0.0550(12) 0.0551(13) 0.0145(10) 0.0174(10) 0.0148(10) O10 0.086(5) 0.110(5) 0.059(4) 0.016(4) 0.008(4) -0.033(4) O11 0.134(7) 0.115(6) 0.110(6) 0.030(5) -0.014(5) -0.046(5) O12 0.188(9) 0.055(5) 0.156(8) 0.025(5) -0.009(7) 0.000(5) O13 0.105(6) 0.167(8) 0.152(7) 0.004(7) 0.052(5) 0.063(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 O2 2.060(5) . ? Ni1 O4 2.075(5) . ? Ni1 O1 2.076(5) . ? Ni1 N1 2.086(5) . ? Ni1 O3 2.088(5) . ? Ni1 N4 2.100(5) . ? C1 N1 1.332(8) . ? C1 C5 1.369(9) . ? C1 H1A 0.9300 . ? C2 N1 1.345(8) . ? C2 C3 1.367(9) . ? C2 H2A 0.9300 . ? C3 C4 1.367(9) . ? C3 H3A 0.9300 . ? C4 C5 1.390(9) . ? C4 H4A 0.9300 . ? C5 C6 1.470(8) . ? C6 C7 1.308(9) . ? C6 H6A 0.9300 . ? C7 C8 1.467(9) . ? C7 H7A 0.9300 . ? C8 N3 1.343(8) . ? C8 C9 1.393(9) . ? C9 C10 1.364(9) . ? C9 H9A 0.9300 . ? C10 N2 1.322(9) . ? C10 H11A 0.9300 . ? C11 N2 1.323(9) . ? C11 N3 1.332(8) . ? C11 H10A 0.9300 . ? C12 N4 1.359(8) . ? C12 C16 1.380(9) . ? C12 H12A 0.9300 . ? C13 N4 1.339(8) . ? C13 C14 1.372(9) . ? C13 H13A 0.9300 . ? C14 C15 1.387(9) . ? C14 H14A 0.9300 . ? C15 C16 1.391(9) . ? C15 H15A 0.9300 . ? C16 C17 1.462(9) . ? C17 C18 1.312(9) . ? C17 H17A 0.9300 . ? C18 C19 1.471(9) . ? C18 H18A 0.9300 . ? C19 N6 1.342(8) . ? C19 C20 1.371(9) . ? C20 C21 1.367(9) . ? C20 H20A 0.9300 . ? C21 N5 1.326(9) . ? C21 H21A 0.9300 . ? C22 N5 1.321(9) . ? C22 N6 1.325(8) . ? C22 H22A 0.9300 . ? O1 H1WA 0.86(3) . ? O1 H1WB 0.82(3) . ? O2 H2WA 0.85(3) . ? O2 H2WB 0.83(3) . ? O3 H3WA 0.81(3) . ? O3 H3WB 0.82(3) . ? O4 H4WA 0.85(3) . ? O4 H4WB 0.84(3) . ? O5 H5WA 0.85(3) . ? O5 H5WB 0.83(3) . ? Cl1 O7 1.335(7) . ? Cl1 O6 1.351(8) . ? Cl1 O9 1.406(6) . ? Cl1 O8 1.418(7) . ? Cl2 O13 1.349(7) . ? Cl2 O11 1.353(8) . ? Cl2 O12 1.400(7) . ? Cl2 O10 1.402(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 O2 Ni1 O4 88.2(2) . . ? O2 Ni1 O1 178.1(2) . . ? O4 Ni1 O1 92.4(2) . . ? O2 Ni1 N1 90.7(2) . . ? O4 Ni1 N1 93.1(2) . . ? O1 Ni1 N1 87.5(2) . . ? O2 Ni1 O3 89.5(2) . . ? O4 Ni1 O3 177.5(2) . . ? O1 Ni1 O3 90.0(2) . . ? N1 Ni1 O3 87.8(2) . . ? O2 Ni1 N4 91.5(2) . . ? O4 Ni1 N4 88.5(2) . . ? O1 Ni1 N4 90.3(2) . . ? N1 Ni1 N4 177.3(2) . . ? O3 Ni1 N4 90.7(2) . . ? N1 C1 C5 125.7(6) . . ? N1 C1 H1A 117.1 . . ? C5 C1 H1A 117.1 . . ? N1 C2 C3 122.9(6) . . ? N1 C2 H2A 118.6 . . ? C3 C2 H2A 118.6 . . ? C2 C3 C4 119.9(7) . . ? C2 C3 H3A 120.0 . . ? C4 C3 H3A 120.0 . . ? C3 C4 C5 118.7(7) . . ? C3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? C1 C5 C4 116.9(6) . . ? C1 C5 C6 120.4(6) . . ? C4 C5 C6 122.7(6) . . ? C7 C6 C5 126.2(7) . . ? C7 C6 H6A 116.9 . . ? C5 C6 H6A 116.9 . . ? C6 C7 C8 125.0(7) . . ? C6 C7 H7A 117.5 . . ? C8 C7 H7A 117.5 . . ? N3 C8 C9 120.5(6) . . ? N3 C8 C7 116.5(6) . . ? C9 C8 C7 123.0(6) . . ? C10 C9 C8 117.0(7) . . ? C10 C9 H9A 121.5 . . ? C8 C9 H9A 121.5 . . ? N2 C10 C9 123.9(7) . . ? N2 C10 H11A 118.0 . . ? C9 C10 H11A 118.0 . . ? N2 C11 N3 127.4(6) . . ? N2 C11 H10A 116.3 . . ? N3 C11 H10A 116.3 . . ? N4 C12 C16 123.8(6) . . ? N4 C12 H12A 118.1 . . ? C16 C12 H12A 118.1 . . ? N4 C13 C14 122.8(6) . . ? N4 C13 H13A 118.6 . . ? C14 C13 H13A 118.6 . . ? C13 C14 C15 119.5(7) . . ? C13 C14 H14A 120.3 . . ? C15 C14 H14A 120.3 . . ? C14 C15 C16 119.2(6) . . ? C14 C15 H15A 120.4 . . ? C16 C15 H15A 120.4 . . ? C12 C16 C15 117.5(6) . . ? C12 C16 C17 118.7(6) . . ? C15 C16 C17 123.8(6) . . ? C18 C17 C16 127.7(7) . . ? C18 C17 H17A 116.2 . . ? C16 C17 H17A 116.2 . . ? C17 C18 C19 125.9(7) . . ? C17 C18 H18A 117.1 . . ? C19 C18 H18A 117.1 . . ? N6 C19 C20 119.6(6) . . ? N6 C19 C18 117.0(6) . . ? C20 C19 C18 123.4(6) . . ? C21 C20 C19 118.0(7) . . ? C21 C20 H20A 121.0 . . ? C19 C20 H20A 121.0 . . ? N5 C21 C20 123.3(7) . . ? N5 C21 H21A 118.3 . . ? C20 C21 H21A 118.3 . . ? N5 C22 N6 127.0(7) . . ? N5 C22 H22A 116.5 . . ? N6 C22 H22A 116.5 . . ? C1 N1 C2 115.8(6) . . ? C1 N1 Ni1 122.1(5) . . ? C2 N1 Ni1 122.1(4) . . ? C10 N2 C11 114.9(6) . . ? C11 N3 C8 116.3(6) . . ? C13 N4 C12 117.2(6) . . ? C13 N4 Ni1 121.9(4) . . ? C12 N4 Ni1 120.7(5) . . ? C22 N5 C21 114.6(6) . . ? C22 N6 C19 117.4(6) . . ? Ni1 O1 H1WA 128(6) . . ? Ni1 O1 H1WB 122(6) . . ? H1WA O1 H1WB 104(6) . . ? Ni1 O2 H2WA 119(5) . . ? Ni1 O2 H2WB 127(5) . . ? H2WA O2 H2WB 110(6) . . ? Ni1 O3 H3WA 127(6) . . ? Ni1 O3 H3WB 104(6) . . ? H3WA O3 H3WB 121(7) . . ? Ni1 O4 H4WA 126(5) . . ? Ni1 O4 H4WB 115(5) . . ? H4WA O4 H4WB 107(5) . . ? H5WA O5 H5WB 108(6) . . ? O7 Cl1 O6 108.9(6) . . ? O7 Cl1 O9 113.4(5) . . ? O6 Cl1 O9 107.2(6) . . ? O7 Cl1 O8 114.3(5) . . ? O6 Cl1 O8 104.5(6) . . ? O9 Cl1 O8 107.9(5) . . ? O13 Cl2 O11 115.4(6) . . ? O13 Cl2 O12 101.8(6) . . ? O11 Cl2 O12 108.5(5) . . ? O13 Cl2 O10 109.5(5) . . ? O11 Cl2 O10 110.8(4) . . ? O12 Cl2 O10 110.4(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 C4 1.0(11) . . . . ? C2 C3 C4 C5 0.2(11) . . . . ? N1 C1 C5 C4 1.2(11) . . . . ? N1 C1 C5 C6 180.0(6) . . . . ? C3 C4 C5 C1 -1.2(10) . . . . ? C3 C4 C5 C6 -179.9(7) . . . . ? C1 C5 C6 C7 -166.1(7) . . . . ? C4 C5 C6 C7 12.5(12) . . . . ? C5 C6 C7 C8 177.2(7) . . . . ? C6 C7 C8 N3 -163.0(7) . . . . ? C6 C7 C8 C9 15.2(12) . . . . ? N3 C8 C9 C10 -0.1(10) . . . . ? C7 C8 C9 C10 -178.3(7) . . . . ? C8 C9 C10 N2 0.4(11) . . . . ? N4 C13 C14 C15 0.2(11) . . . . ? C13 C14 C15 C16 -1.5(11) . . . . ? N4 C12 C16 C15 0.1(10) . . . . ? N4 C12 C16 C17 180.0(6) . . . . ? C14 C15 C16 C12 1.3(10) . . . . ? C14 C15 C16 C17 -178.6(7) . . . . ? C12 C16 C17 C18 176.0(7) . . . . ? C15 C16 C17 C18 -4.1(12) . . . . ? C16 C17 C18 C19 179.2(7) . . . . ? C17 C18 C19 N6 176.6(7) . . . . ? C17 C18 C19 C20 -4.3(12) . . . . ? N6 C19 C20 C21 -1.1(11) . . . . ? C18 C19 C20 C21 179.9(7) . . . . ? C19 C20 C21 N5 -2.1(12) . . . . ? C5 C1 N1 C2 -0.1(10) . . . . ? C5 C1 N1 Ni1 177.2(5) . . . . ? C3 C2 N1 C1 -1.0(10) . . . . ? C3 C2 N1 Ni1 -178.4(5) . . . . ? O2 Ni1 N1 C1 131.5(5) . . . . ? O4 Ni1 N1 C1 43.3(5) . . . . ? O1 Ni1 N1 C1 -49.0(5) . . . . ? O3 Ni1 N1 C1 -139.0(5) . . . . ? N4 Ni1 N1 C1 -82(5) . . . . ? O2 Ni1 N1 C2 -51.3(5) . . . . ? O4 Ni1 N1 C2 -139.5(5) . . . . ? O1 Ni1 N1 C2 128.2(5) . . . . ? O3 Ni1 N1 C2 38.2(5) . . . . ? N4 Ni1 N1 C2 95(5) . . . . ? C9 C10 N2 C11 -0.4(11) . . . . ? N3 C11 N2 C10 0.1(12) . . . . ? N2 C11 N3 C8 0.1(11) . . . . ? C9 C8 N3 C11 -0.1(10) . . . . ? C7 C8 N3 C11 178.1(6) . . . . ? C14 C13 N4 C12 1.2(10) . . . . ? C14 C13 N4 Ni1 -173.2(5) . . . . ? C16 C12 N4 C13 -1.4(10) . . . . ? C16 C12 N4 Ni1 173.1(5) . . . . ? O2 Ni1 N4 C13 -142.1(5) . . . . ? O4 Ni1 N4 C13 -54.0(5) . . . . ? O1 Ni1 N4 C13 38.4(5) . . . . ? N1 Ni1 N4 C13 71(5) . . . . ? O3 Ni1 N4 C13 128.4(5) . . . . ? O2 Ni1 N4 C12 43.6(5) . . . . ? O4 Ni1 N4 C12 131.8(5) . . . . ? O1 Ni1 N4 C12 -135.8(5) . . . . ? N1 Ni1 N4 C12 -103(5) . . . . ? O3 Ni1 N4 C12 -45.9(5) . . . . ? N6 C22 N5 C21 -0.9(12) . . . . ? C20 C21 N5 C22 3.0(12) . . . . ? N5 C22 N6 C19 -2.1(12) . . . . ? C20 C19 N6 C22 3.0(11) . . . . ? C18 C19 N6 C22 -177.9(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1WA O5 0.86(3) 1.86(4) 2.689(7) 164(8) . O1 H1WB O13 0.82(3) 2.16(5) 2.906(10) 152(9) . O2 H2WA O5 0.85(3) 1.91(3) 2.748(7) 170(7) 1_455 O2 H2WB N3 0.83(3) 2.05(3) 2.860(7) 169(7) 2_566 O3 H3WA N2 0.81(3) 2.00(3) 2.803(7) 169(7) 1_565 O3 H3WB O7 0.82(3) 2.19(6) 2.834(9) 135(7) . O4 H4WA N5 0.85(3) 2.00(4) 2.791(7) 155(7) 1_545 O4 H4WB O10 0.84(3) 1.96(4) 2.781(8) 165(8) 1_455 O5 H5WA O8 0.85(3) 1.99(4) 2.798(9) 159(8) . O5 H5WB N6 0.83(3) 1.94(3) 2.763(7) 171(8) 2_675 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.623 _refine_diff_density_min -0.498 _refine_diff_density_rms 0.107 # Attachment '5.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 662566' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H28 Cl2 N6 O13 Zn' _chemical_formula_weight 720.77 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' Zn Zn 0.2839 1.4301 '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 7.9922(8) _cell_length_b 14.0221(13) _cell_length_c 14.1085(14) _cell_angle_alpha 102.5100(10) _cell_angle_beta 94.5720(10) _cell_angle_gamma 103.0340(10) _cell_volume 1490.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4275 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.47 _exptl_crystal_description prism _exptl_crystal_colour coloress _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 1.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7382 _exptl_absorpt_correction_T_max 0.8134 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8385 _diffrn_reflns_av_R_equivalents 0.0125 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5712 _reflns_number_gt 4769 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1072P)^2^+3.3905P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5712 _refine_ls_number_parameters 429 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0674 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1794 _refine_ls_wR_factor_gt 0.1690 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.996 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.21421(6) 0.73796(3) 0.27212(3) 0.03354(17) Uani 1 1 d . . . C1 C 0.2373(6) 0.5759(3) 0.3812(3) 0.0364(9) Uani 1 1 d . . . H1A H 0.2483 0.5416 0.3187 0.044 Uiso 1 1 calc R . . C2 C 0.2018(6) 0.7185(3) 0.4835(3) 0.0404(9) Uani 1 1 d . . . H2A H 0.1896 0.7842 0.4936 0.049 Uiso 1 1 calc R . . C3 C 0.2049(7) 0.6752(3) 0.5619(3) 0.0464(11) Uani 1 1 d . . . H3A H 0.1925 0.7110 0.6235 0.056 Uiso 1 1 calc R . . C4 C 0.2262(6) 0.5793(3) 0.5492(3) 0.0439(10) Uani 1 1 d . . . H4A H 0.2285 0.5494 0.6019 0.053 Uiso 1 1 calc R . . C5 C 0.2445(5) 0.5272(3) 0.4561(3) 0.0353(9) Uani 1 1 d . . . C6 C 0.2694(6) 0.4249(3) 0.4350(3) 0.0383(9) Uani 1 1 d . . . H6A H 0.3054 0.4013 0.3752 0.046 Uiso 1 1 calc R . . C7 C 0.2447(6) 0.3631(3) 0.4945(3) 0.0387(9) Uani 1 1 d . . . H7A H 0.2136 0.3871 0.5557 0.046 Uiso 1 1 calc R . . C8 C 0.2637(5) 0.2590(3) 0.4696(3) 0.0353(9) Uani 1 1 d . . . C9 C 0.3448(6) 0.2212(3) 0.3916(3) 0.0417(10) Uani 1 1 d . . . H9A H 0.3937 0.2616 0.3517 0.050 Uiso 1 1 calc R . . C10 C 0.3503(6) 0.1219(4) 0.3757(4) 0.0474(11) Uani 1 1 d . . . H11A H 0.4062 0.0958 0.3246 0.057 Uiso 1 1 calc R . . C11 C 0.2044(6) 0.1037(3) 0.5027(4) 0.0452(10) Uani 1 1 d . . . H10A H 0.1548 0.0624 0.5418 0.054 Uiso 1 1 calc R . . C12 C 0.1983(5) 0.9031(3) 0.1637(3) 0.0345(8) Uani 1 1 d . . . H12A H 0.1571 0.9302 0.2207 0.041 Uiso 1 1 calc R . . C13 C 0.2839(6) 0.7719(3) 0.0710(3) 0.0409(10) Uani 1 1 d . . . H13A H 0.3035 0.7078 0.0622 0.049 Uiso 1 1 calc R . . C14 C 0.3117(6) 0.8221(4) -0.0027(3) 0.0452(10) Uani 1 1 d . . . H14A H 0.3499 0.7923 -0.0597 0.054 Uiso 1 1 calc R . . C15 C 0.2822(6) 0.9170(3) 0.0090(3) 0.0411(10) Uani 1 1 d . . . H15A H 0.3016 0.9521 -0.0396 0.049 Uiso 1 1 calc R . . C16 C 0.2228(5) 0.9595(3) 0.0946(3) 0.0350(8) Uani 1 1 d . . . C17 C 0.1846(6) 1.0594(3) 0.1147(3) 0.0383(9) Uani 1 1 d . . . H17A H 0.1395 1.0785 0.1726 0.046 Uiso 1 1 calc R . . C18 C 0.2075(6) 1.1246(3) 0.0592(3) 0.0398(9) Uani 1 1 d . . . H18A H 0.2538 1.1068 0.0014 0.048 Uiso 1 1 calc R . . C19 C 0.1659(6) 1.2223(3) 0.0815(3) 0.0365(9) Uani 1 1 d . . . C20 C 0.0852(6) 1.2569(3) 0.1617(3) 0.0434(10) Uani 1 1 d . . . H20A H 0.0535 1.2174 0.2056 0.052 Uiso 1 1 calc R . . C21 C 0.0542(6) 1.3498(3) 0.1737(4) 0.0476(11) Uani 1 1 d . . . H21A H -0.0019 1.3725 0.2261 0.057 Uiso 1 1 calc R . . C22 C 0.1756(7) 1.3716(3) 0.0392(4) 0.0493(11) Uani 1 1 d . . . H22A H 0.2087 1.4122 -0.0037 0.059 Uiso 1 1 calc R . . N1 N 0.2157(4) 0.6694(2) 0.3929(3) 0.0349(7) Uani 1 1 d . . . N2 N 0.2791(5) 0.0616(3) 0.4300(3) 0.0478(9) Uani 1 1 d . . . N3 N 0.1929(5) 0.1995(3) 0.5260(3) 0.0395(8) Uani 1 1 d . . . N4 N 0.2302(5) 0.8115(2) 0.1540(3) 0.0348(7) Uani 1 1 d . . . N5 N 0.1003(6) 1.4100(3) 0.1138(3) 0.0482(9) Uani 1 1 d . . . N6 N 0.2085(5) 1.2813(3) 0.0195(3) 0.0426(8) Uani 1 1 d . . . O1 O 0.4435(5) 0.6916(3) 0.2405(4) 0.0658(11) Uani 1 1 d D . . H1WA H 0.527(7) 0.720(5) 0.216(5) 0.099 Uiso 1 1 d D . . H1WB H 0.457(9) 0.637(3) 0.247(6) 0.099 Uiso 1 1 d D . . O2 O -0.0151(4) 0.7802(3) 0.3061(2) 0.0427(7) Uani 1 1 d D . . H2WA H -0.089(6) 0.774(5) 0.259(3) 0.064 Uiso 1 1 d D . . H2WB H -0.059(7) 0.775(4) 0.357(3) 0.064 Uiso 1 1 d D . . O3 O 0.3629(4) 0.8754(2) 0.3706(3) 0.0465(8) Uani 1 1 d D . . H3WA H 0.331(8) 0.922(3) 0.401(4) 0.070 Uiso 1 1 d D . . H3WB H 0.450(6) 0.889(4) 0.340(4) 0.070 Uiso 1 1 d D . . O4 O 0.0587(4) 0.6049(2) 0.1753(3) 0.0445(7) Uani 1 1 d D . . H4WA H 0.073(7) 0.548(3) 0.144(4) 0.067 Uiso 1 1 d D . . H4WB H -0.036(5) 0.597(4) 0.196(4) 0.067 Uiso 1 1 d D . . O5 O 0.7225(5) 0.7808(2) 0.1694(2) 0.0458(7) Uani 1 1 d D . . H5WA H 0.721(8) 0.840(2) 0.175(4) 0.069 Uiso 1 1 d D . . H5WB H 0.755(8) 0.762(4) 0.116(3) 0.069 Uiso 1 1 d D . . Cl1 Cl 0.75975(15) 1.04930(8) 0.27117(8) 0.0464(3) Uani 1 1 d . . . O6 O 0.9168(9) 1.1065(6) 0.3272(5) 0.1405(19) Uani 1 1 d . . . O7 O 0.6670(8) 0.9999(5) 0.3295(6) 0.1256(14) Uani 1 1 d . . . O8 O 0.8117(9) 0.9905(4) 0.1879(4) 0.1094(10) Uani 1 1 d . . . O9 O 0.6835(9) 1.1208(4) 0.2401(4) 0.1043(19) Uani 1 1 d . . . Cl2 Cl 0.61560(15) 0.45492(9) 0.19431(9) 0.0494(3) Uani 1 1 d . . . O10 O 0.7692(6) 0.5158(5) 0.2522(3) 0.0990(19) Uani 1 1 d . . . O11 O 0.6274(8) 0.4487(5) 0.0973(4) 0.1239(14) Uani 1 1 d . . . O12 O 0.5868(9) 0.3569(4) 0.2103(5) 0.1138(12) Uani 1 1 d . . . O13 O 0.4750(8) 0.4871(5) 0.2255(6) 0.1297(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 Zn1 0.0403(3) 0.0248(3) 0.0417(3) 0.01415(19) 0.0124(2) 0.01242(19) C1 0.046(2) 0.030(2) 0.036(2) 0.0099(16) 0.0098(17) 0.0117(17) C2 0.050(2) 0.028(2) 0.044(2) 0.0062(17) 0.0089(19) 0.0115(17) C3 0.063(3) 0.035(2) 0.039(2) 0.0031(18) 0.007(2) 0.013(2) C4 0.059(3) 0.037(2) 0.036(2) 0.0123(18) 0.0032(19) 0.011(2) C5 0.041(2) 0.0261(19) 0.041(2) 0.0115(16) 0.0039(17) 0.0089(16) C6 0.048(2) 0.030(2) 0.040(2) 0.0094(17) 0.0082(18) 0.0134(17) C7 0.049(2) 0.031(2) 0.040(2) 0.0098(17) 0.0115(18) 0.0142(18) C8 0.039(2) 0.031(2) 0.039(2) 0.0122(17) 0.0044(17) 0.0117(16) C9 0.044(2) 0.036(2) 0.050(3) 0.0158(19) 0.015(2) 0.0125(18) C10 0.046(3) 0.042(2) 0.059(3) 0.010(2) 0.015(2) 0.019(2) C11 0.054(3) 0.032(2) 0.055(3) 0.020(2) 0.010(2) 0.0122(19) C12 0.040(2) 0.0276(19) 0.041(2) 0.0122(16) 0.0120(17) 0.0119(16) C13 0.051(3) 0.029(2) 0.045(2) 0.0073(17) 0.0103(19) 0.0155(18) C14 0.057(3) 0.043(2) 0.038(2) 0.0072(19) 0.013(2) 0.018(2) C15 0.052(3) 0.039(2) 0.036(2) 0.0154(18) 0.0095(19) 0.0135(19) C16 0.037(2) 0.032(2) 0.039(2) 0.0129(17) 0.0074(17) 0.0112(16) C17 0.046(2) 0.030(2) 0.042(2) 0.0117(17) 0.0101(18) 0.0109(17) C18 0.052(3) 0.033(2) 0.039(2) 0.0109(17) 0.0127(19) 0.0146(18) C19 0.043(2) 0.031(2) 0.038(2) 0.0131(16) 0.0057(17) 0.0104(17) C20 0.049(3) 0.039(2) 0.046(2) 0.0160(19) 0.012(2) 0.0104(19) C21 0.053(3) 0.038(2) 0.051(3) 0.004(2) 0.014(2) 0.015(2) C22 0.070(3) 0.033(2) 0.050(3) 0.016(2) 0.009(2) 0.017(2) N1 0.0406(18) 0.0268(16) 0.0405(18) 0.0119(14) 0.0091(15) 0.0100(14) N2 0.055(2) 0.0295(18) 0.064(3) 0.0126(17) 0.0103(19) 0.0174(17) N3 0.051(2) 0.0321(18) 0.0417(19) 0.0158(15) 0.0105(16) 0.0144(15) N4 0.0420(19) 0.0258(16) 0.0410(19) 0.0118(14) 0.0135(15) 0.0112(14) N5 0.061(2) 0.0330(19) 0.053(2) 0.0086(17) 0.0076(19) 0.0172(17) N6 0.060(2) 0.0341(18) 0.0392(19) 0.0145(15) 0.0123(17) 0.0166(17) O1 0.058(2) 0.062(2) 0.111(3) 0.055(2) 0.047(2) 0.0388(19) O2 0.0437(17) 0.0530(19) 0.0423(17) 0.0186(15) 0.0169(14) 0.0237(15) O3 0.0481(19) 0.0249(14) 0.064(2) 0.0082(14) 0.0075(15) 0.0059(13) O4 0.0539(19) 0.0257(14) 0.0525(19) 0.0058(13) 0.0140(15) 0.0084(13) O5 0.058(2) 0.0427(17) 0.0430(18) 0.0134(14) 0.0175(15) 0.0191(15) Cl1 0.0509(6) 0.0415(6) 0.0476(6) 0.0089(5) 0.0156(5) 0.0118(5) O6 0.112(5) 0.164(6) 0.112(4) 0.007(5) -0.029(4) 0.007(5) O7 0.117(5) 0.139(6) 0.165(7) 0.107(2) 0.066(4) 0.037(4) O8 0.158(6) 0.084(3) 0.104(3) 0.021(3) 0.057(3) 0.054(3) O9 0.168(6) 0.095(4) 0.086(3) 0.044(3) 0.037(4) 0.078(4) Cl2 0.0455(6) 0.0528(7) 0.0529(7) 0.0147(5) 0.0121(5) 0.0145(5) O10 0.075(3) 0.137(5) 0.057(3) 0.026(3) 0.005(2) -0.030(3) O11 0.106(3) 0.151(6) 0.086(4) 0.033(4) 0.001(3) -0.026(4) O12 0.148(5) 0.078(3) 0.101(3) 0.023(3) 0.000(4) 0.004(3) O13 0.105(4) 0.112(5) 0.186(7) 0.024(4) 0.060(4) 0.053(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 2.108(3) . ? Zn1 O4 2.114(3) . ? Zn1 O1 2.127(3) . ? Zn1 N1 2.131(3) . ? Zn1 N4 2.139(3) . ? Zn1 O3 2.145(3) . ? C1 N1 1.337(5) . ? C1 C5 1.381(6) . ? C1 H1A 0.9300 . ? C2 N1 1.340(6) . ? C2 C3 1.372(7) . ? C2 H2A 0.9300 . ? C3 C4 1.369(6) . ? C3 H3A 0.9300 . ? C4 C5 1.395(6) . ? C4 H4A 0.9300 . ? C5 C6 1.463(5) . ? C6 C7 1.326(6) . ? C6 H6A 0.9300 . ? C7 C8 1.471(5) . ? C7 H7A 0.9300 . ? C8 N3 1.341(5) . ? C8 C9 1.389(6) . ? C9 C10 1.372(6) . ? C9 H9A 0.9300 . ? C10 N2 1.327(6) . ? C10 H11A 0.9300 . ? C11 N2 1.324(6) . ? C11 N3 1.338(5) . ? C11 H10A 0.9300 . ? C12 N4 1.346(5) . ? C12 C16 1.382(6) . ? C12 H12A 0.9300 . ? C13 N4 1.330(5) . ? C13 C14 1.383(6) . ? C13 H13A 0.9300 . ? C14 C15 1.380(6) . ? C14 H14A 0.9300 . ? C15 C16 1.395(6) . ? C15 H15A 0.9300 . ? C16 C17 1.473(6) . ? C17 C18 1.318(6) . ? C17 H17A 0.9300 . ? C18 C19 1.457(6) . ? C18 H18A 0.9300 . ? C19 N6 1.342(5) . ? C19 C20 1.397(6) . ? C20 C21 1.357(6) . ? C20 H20A 0.9300 . ? C21 N5 1.334(6) . ? C21 H21A 0.9300 . ? C22 N6 1.327(6) . ? C22 N5 1.328(6) . ? C22 H22A 0.9300 . ? O1 H1WA 0.84(3) . ? O1 H1WB 0.82(3) . ? O2 H2WA 0.83(3) . ? O2 H2WB 0.83(3) . ? O3 H3WA 0.81(3) . ? O3 H3WB 0.85(3) . ? O4 H4WA 0.86(3) . ? O4 H4WB 0.83(3) . ? O5 H5WA 0.82(3) . ? O5 H5WB 0.83(3) . ? Cl1 O7 1.349(5) . ? Cl1 O6 1.399(6) . ? Cl1 O9 1.411(5) . ? Cl1 O8 1.430(5) . ? Cl2 O11 1.365(6) . ? Cl2 O13 1.372(6) . ? Cl2 O10 1.403(5) . ? Cl2 O12 1.412(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 O2 Zn1 O4 88.32(14) . . ? O2 Zn1 O1 178.07(12) . . ? O4 Zn1 O1 91.07(16) . . ? O2 Zn1 N1 90.54(13) . . ? O4 Zn1 N1 93.03(13) . . ? O1 Zn1 N1 87.66(14) . . ? O2 Zn1 N4 91.99(13) . . ? O4 Zn1 N4 89.79(13) . . ? O1 Zn1 N4 89.84(14) . . ? N1 Zn1 N4 176.27(13) . . ? O2 Zn1 O3 89.42(14) . . ? O4 Zn1 O3 177.67(13) . . ? O1 Zn1 O3 91.21(16) . . ? N1 Zn1 O3 87.54(13) . . ? N4 Zn1 O3 89.74(13) . . ? N1 C1 C5 124.1(4) . . ? N1 C1 H1A 117.9 . . ? C5 C1 H1A 117.9 . . ? N1 C2 C3 122.4(4) . . ? N1 C2 H2A 118.8 . . ? C3 C2 H2A 118.8 . . ? C4 C3 C2 119.9(4) . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? C3 C4 C5 118.9(4) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? C1 C5 C4 117.3(4) . . ? C1 C5 C6 119.5(4) . . ? C4 C5 C6 123.2(4) . . ? C7 C6 C5 125.1(4) . . ? C7 C6 H6A 117.5 . . ? C5 C6 H6A 117.5 . . ? C6 C7 C8 123.8(4) . . ? C6 C7 H7A 118.1 . . ? C8 C7 H7A 118.1 . . ? N3 C8 C9 120.5(4) . . ? N3 C8 C7 115.7(4) . . ? C9 C8 C7 123.8(4) . . ? C10 C9 C8 117.6(4) . . ? C10 C9 H9A 121.2 . . ? C8 C9 H9A 121.2 . . ? N2 C10 C9 122.9(4) . . ? N2 C10 H11A 118.6 . . ? C9 C10 H11A 118.6 . . ? N2 C11 N3 126.8(4) . . ? N2 C11 H10A 116.6 . . ? N3 C11 H10A 116.6 . . ? N4 C12 C16 124.3(4) . . ? N4 C12 H12A 117.9 . . ? C16 C12 H12A 117.9 . . ? N4 C13 C14 122.7(4) . . ? N4 C13 H13A 118.7 . . ? C14 C13 H13A 118.7 . . ? C15 C14 C13 119.3(4) . . ? C15 C14 H14A 120.3 . . ? C13 C14 H14A 120.3 . . ? C14 C15 C16 119.2(4) . . ? C14 C15 H15A 120.4 . . ? C16 C15 H15A 120.4 . . ? C12 C16 C15 117.1(4) . . ? C12 C16 C17 118.9(4) . . ? C15 C16 C17 124.0(4) . . ? C18 C17 C16 126.9(4) . . ? C18 C17 H17A 116.6 . . ? C16 C17 H17A 116.6 . . ? C17 C18 C19 125.0(4) . . ? C17 C18 H18A 117.5 . . ? C19 C18 H18A 117.5 . . ? N6 C19 C20 119.1(4) . . ? N6 C19 C18 116.5(4) . . ? C20 C19 C18 124.4(4) . . ? C21 C20 C19 118.1(4) . . ? C21 C20 H20A 120.9 . . ? C19 C20 H20A 120.9 . . ? N5 C21 C20 123.2(4) . . ? N5 C21 H21A 118.4 . . ? C20 C21 H21A 118.4 . . ? N6 C22 N5 126.6(4) . . ? N6 C22 H22A 116.7 . . ? N5 C22 H22A 116.7 . . ? C1 N1 C2 117.4(4) . . ? C1 N1 Zn1 120.6(3) . . ? C2 N1 Zn1 122.0(3) . . ? C11 N2 C10 115.6(4) . . ? C11 N3 C8 116.6(4) . . ? C13 N4 C12 117.4(3) . . ? C13 N4 Zn1 121.4(3) . . ? C12 N4 Zn1 121.0(3) . . ? C22 N5 C21 115.1(4) . . ? C22 N6 C19 117.8(4) . . ? Zn1 O1 H1WA 129(5) . . ? Zn1 O1 H1WB 122(5) . . ? H1WA O1 H1WB 109(6) . . ? Zn1 O2 H2WA 116(4) . . ? Zn1 O2 H2WB 125(4) . . ? H2WA O2 H2WB 112(5) . . ? Zn1 O3 H3WA 130(5) . . ? Zn1 O3 H3WB 100(4) . . ? H3WA O3 H3WB 117(5) . . ? Zn1 O4 H4WA 137(4) . . ? Zn1 O4 H4WB 104(4) . . ? H4WA O4 H4WB 111(5) . . ? H5WA O5 H5WB 107(5) . . ? O7 Cl1 O6 107.4(5) . . ? O7 Cl1 O9 113.6(4) . . ? O6 Cl1 O9 104.5(5) . . ? O7 Cl1 O8 117.9(4) . . ? O6 Cl1 O8 103.7(5) . . ? O9 Cl1 O8 108.4(3) . . ? O11 Cl2 O13 114.1(5) . . ? O11 Cl2 O10 110.6(3) . . ? O13 Cl2 O10 110.5(4) . . ? O11 Cl2 O12 108.7(4) . . ? O13 Cl2 O12 103.4(4) . . ? O10 Cl2 O12 109.3(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 C2 C3 C4 1.3(7) . . . . ? C2 C3 C4 C5 0.0(7) . . . . ? N1 C1 C5 C4 0.6(7) . . . . ? N1 C1 C5 C6 -179.7(4) . . . . ? C3 C4 C5 C1 -0.9(7) . . . . ? C3 C4 C5 C6 179.4(4) . . . . ? C1 C5 C6 C7 -166.0(4) . . . . ? C4 C5 C6 C7 13.7(7) . . . . ? C5 C6 C7 C8 177.3(4) . . . . ? C6 C7 C8 N3 -163.7(4) . . . . ? C6 C7 C8 C9 14.6(7) . . . . ? N3 C8 C9 C10 -0.5(7) . . . . ? C7 C8 C9 C10 -178.8(4) . . . . ? C8 C9 C10 N2 1.3(7) . . . . ? N4 C13 C14 C15 -0.4(7) . . . . ? C13 C14 C15 C16 -0.8(7) . . . . ? N4 C12 C16 C15 1.0(6) . . . . ? N4 C12 C16 C17 -179.4(4) . . . . ? C14 C15 C16 C12 0.5(6) . . . . ? C14 C15 C16 C17 -179.1(4) . . . . ? C12 C16 C17 C18 176.9(4) . . . . ? C15 C16 C17 C18 -3.5(7) . . . . ? C16 C17 C18 C19 179.3(4) . . . . ? C17 C18 C19 N6 175.9(4) . . . . ? C17 C18 C19 C20 -4.5(8) . . . . ? N6 C19 C20 C21 -0.4(7) . . . . ? C18 C19 C20 C21 180.0(4) . . . . ? C19 C20 C21 N5 -1.4(8) . . . . ? C5 C1 N1 C2 0.6(6) . . . . ? C5 C1 N1 Zn1 178.2(3) . . . . ? C3 C2 N1 C1 -1.6(7) . . . . ? C3 C2 N1 Zn1 -179.1(4) . . . . ? O2 Zn1 N1 C1 131.1(3) . . . . ? O4 Zn1 N1 C1 42.8(3) . . . . ? O1 Zn1 N1 C1 -48.2(3) . . . . ? N4 Zn1 N1 C1 -96.2(18) . . . . ? O3 Zn1 N1 C1 -139.5(3) . . . . ? O2 Zn1 N1 C2 -51.4(3) . . . . ? O4 Zn1 N1 C2 -139.8(3) . . . . ? O1 Zn1 N1 C2 129.3(4) . . . . ? N4 Zn1 N1 C2 81.2(19) . . . . ? O3 Zn1 N1 C2 38.0(3) . . . . ? N3 C11 N2 C10 0.4(8) . . . . ? C9 C10 N2 C11 -1.2(7) . . . . ? N2 C11 N3 C8 0.3(7) . . . . ? C9 C8 N3 C11 -0.3(6) . . . . ? C7 C8 N3 C11 178.2(4) . . . . ? C14 C13 N4 C12 1.8(7) . . . . ? C14 C13 N4 Zn1 -173.5(4) . . . . ? C16 C12 N4 C13 -2.1(6) . . . . ? C16 C12 N4 Zn1 173.2(3) . . . . ? O2 Zn1 N4 C13 -142.2(3) . . . . ? O4 Zn1 N4 C13 -53.9(3) . . . . ? O1 Zn1 N4 C13 37.2(4) . . . . ? N1 Zn1 N4 C13 85.2(19) . . . . ? O3 Zn1 N4 C13 128.4(3) . . . . ? O2 Zn1 N4 C12 42.6(3) . . . . ? O4 Zn1 N4 C12 131.0(3) . . . . ? O1 Zn1 N4 C12 -138.0(3) . . . . ? N1 Zn1 N4 C12 -90.0(19) . . . . ? O3 Zn1 N4 C12 -46.8(3) . . . . ? N6 C22 N5 C21 -0.2(8) . . . . ? C20 C21 N5 C22 1.7(7) . . . . ? N5 C22 N6 C19 -1.6(8) . . . . ? C20 C19 N6 C22 1.8(7) . . . . ? C18 C19 N6 C22 -178.6(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1WA O5 0.84(3) 1.84(3) 2.680(5) 175(8) . O1 H1WB O13 0.82(3) 2.09(3) 2.898(7) 166(8) . O2 H2WA O5 0.83(3) 1.92(3) 2.737(5) 167(6) 1_455 O2 H2WB N3 0.83(3) 2.05(3) 2.852(5) 162(6) 2_566 O3 H3WA N2 0.81(3) 2.05(4) 2.809(5) 157(6) 1_565 O3 H3WB O7 0.85(3) 2.09(4) 2.835(6) 145(5) . O4 H4WA N5 0.86(3) 1.96(3) 2.786(5) 162(6) 1_545 O4 H4WB O10 0.83(3) 2.04(4) 2.788(6) 151(6) 1_455 O5 H5WA O8 0.82(3) 2.03(4) 2.814(6) 159(6) . O5 H5WB N6 0.83(3) 1.94(3) 2.759(5) 170(6) 2_675 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.660 _refine_diff_density_min -0.454 _refine_diff_density_rms 0.100 # Attachment '6.cif' data_6 _database_code_depnum_ccdc_archive 'CCDC 662567' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 Cu N8 O10' _chemical_formula_weight 626.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.778(4) _cell_length_b 12.825(6) _cell_length_c 10.618(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.422(7) _cell_angle_gamma 90.00 _cell_volume 1325.7(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 552 _cell_measurement_theta_min 2.497 _cell_measurement_theta_max 25.339 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 646 _exptl_absorpt_coefficient_mu 0.895 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7751 _exptl_absorpt_correction_T_max 0.8775 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.5 _diffrn_reflns_number 5435 _diffrn_reflns_av_R_equivalents 0.0490 _diffrn_reflns_av_sigmaI/netI 0.0816 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2335 _reflns_number_gt 1391 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0718P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2335 _refine_ls_number_parameters 199 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1034 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1500 _refine_ls_wR_factor_gt 0.1356 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.991 _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 Cu1 Cu 0.0000 0.5000 0.0000 0.0404(3) Uani 1 2 d S . . C1 C 0.1003(5) 0.5649(4) 0.2582(5) 0.0429(13) Uani 1 1 d . . . H1A H 0.1839 0.5436 0.2319 0.052 Uiso 1 1 calc R . . C2 C -0.1310(5) 0.5909(4) 0.2142(5) 0.0462(14) Uani 1 1 d . . . H2A H -0.2097 0.5885 0.1577 0.055 Uiso 1 1 calc R . . C3 C -0.1411(6) 0.6281(5) 0.3335(5) 0.0529(15) Uani 1 1 d . . . H3A H -0.2257 0.6495 0.3576 0.063 Uiso 1 1 calc R . . C4 C -0.0255(6) 0.6339(4) 0.4178(5) 0.0511(14) Uani 1 1 d . . . H4A H -0.0313 0.6589 0.4993 0.061 Uiso 1 1 calc R . . C5 C 0.0990(5) 0.6021(4) 0.3798(5) 0.0414(13) Uani 1 1 d . . . C6 C 0.2303(5) 0.6071(4) 0.4592(5) 0.0473(14) Uani 1 1 d . . . H6A H 0.3093 0.5986 0.4180 0.057 Uiso 1 1 calc R . . C7 C 0.2484(5) 0.6225(4) 0.5836(5) 0.0457(13) Uani 1 1 d . . . H7A H 0.1714 0.6337 0.6271 0.055 Uiso 1 1 calc R . . C8 C 0.3827(5) 0.6226(4) 0.6547(5) 0.0447(13) Uani 1 1 d . . . C9 C 0.5052(6) 0.6352(5) 0.5997(5) 0.0571(16) Uani 1 1 d . . . H9A H 0.5054 0.6460 0.5131 0.069 Uiso 1 1 calc R . . C10 C 0.6246(6) 0.6313(5) 0.6764(6) 0.0648(18) Uani 1 1 d . . . H10A H 0.7067 0.6398 0.6399 0.078 Uiso 1 1 calc R . . C11 C 0.5086(6) 0.6056(5) 0.8455(5) 0.0571(16) Uani 1 1 d . . . H11A H 0.5097 0.5944 0.9321 0.069 Uiso 1 1 calc R . . N1 N -0.0116(4) 0.5576(3) 0.1757(4) 0.0418(11) Uani 1 1 d . . . N3 N 0.3854(4) 0.6093(4) 0.7808(4) 0.0480(12) Uani 1 1 d . . . N2 N 0.6305(5) 0.6161(4) 0.8010(5) 0.0564(13) Uani 1 1 d . . . N4 N 0.0232(5) 0.1924(4) 0.2847(5) 0.0515(12) Uani 1 1 d . . . O1 O 0.2051(4) 0.5933(4) -0.0175(4) 0.0629(12) Uani 1 1 d D . . H2W H 0.239(6) 0.601(5) -0.087(3) 0.094 Uiso 1 1 d D . . H1W H 0.248(6) 0.626(5) 0.040(4) 0.094 Uiso 1 1 d D . . O2 O 0.1084(3) 0.3769(3) 0.0689(3) 0.0469(10) Uani 1 1 d D . . H4W H 0.186(3) 0.388(4) 0.100(5) 0.070 Uiso 1 1 d D . . H3W H 0.065(5) 0.334(4) 0.110(5) 0.070 Uiso 1 1 d D . . O3 O -0.0366(7) 0.1307(6) 0.3404(7) 0.162(3) Uani 1 1 d . . . O4 O -0.0379(4) 0.2392(4) 0.1986(5) 0.0997(19) Uani 1 1 d . . . O5 O 0.1365(5) 0.2129(5) 0.3269(5) 0.1076(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0342(5) 0.0565(6) 0.0282(5) 0.0015(5) -0.0088(3) 0.0005(5) C1 0.034(3) 0.062(4) 0.032(3) 0.001(3) -0.003(2) -0.002(3) C2 0.040(3) 0.057(3) 0.040(3) -0.001(3) -0.005(2) 0.001(3) C3 0.039(3) 0.073(4) 0.046(4) -0.008(3) 0.003(3) 0.009(3) C4 0.048(3) 0.062(4) 0.041(3) -0.008(3) -0.003(3) 0.000(3) C5 0.039(3) 0.052(3) 0.032(3) 0.003(3) -0.005(2) -0.003(3) C6 0.041(3) 0.062(4) 0.038(3) -0.002(3) -0.004(2) 0.000(3) C7 0.041(3) 0.058(3) 0.036(3) -0.003(3) -0.007(2) 0.001(3) C8 0.044(3) 0.048(3) 0.039(3) -0.006(3) -0.008(2) 0.000(3) C9 0.048(4) 0.085(4) 0.037(3) 0.006(3) -0.005(3) -0.006(3) C10 0.046(3) 0.088(5) 0.059(4) 0.010(4) -0.002(3) -0.008(3) C11 0.063(4) 0.067(4) 0.038(3) 0.001(3) -0.014(3) 0.004(3) N1 0.039(2) 0.054(3) 0.031(2) 0.000(2) -0.0060(19) 0.000(2) N3 0.044(3) 0.063(3) 0.035(3) -0.005(2) -0.007(2) -0.001(2) N2 0.045(3) 0.073(3) 0.048(3) 0.005(3) -0.012(2) -0.003(3) N4 0.041(3) 0.065(3) 0.048(3) 0.019(3) -0.001(2) -0.005(3) O1 0.046(2) 0.099(3) 0.042(2) -0.002(2) -0.0041(19) -0.024(2) O2 0.032(2) 0.062(3) 0.043(2) 0.0069(19) -0.0133(17) -0.0037(19) O3 0.125(5) 0.159(6) 0.189(7) 0.104(6) -0.055(5) -0.063(5) O4 0.053(3) 0.147(5) 0.096(4) 0.071(4) -0.007(3) -0.006(3) O5 0.061(3) 0.141(5) 0.116(4) 0.031(4) -0.021(3) -0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 2.001(4) 3_565 ? Cu1 O2 2.001(4) . ? Cu1 N1 2.020(4) . ? Cu1 N1 2.020(4) 3_565 ? Cu1 O1 2.358(4) . ? Cu1 O1 2.358(4) 3_565 ? C1 N1 1.340(5) . ? C1 C5 1.378(7) . ? C1 H1A 0.9300 . ? C2 N1 1.343(6) . ? C2 C3 1.366(7) . ? C2 H2A 0.9300 . ? C3 C4 1.376(7) . ? C3 H3A 0.9300 . ? C4 C5 1.380(7) . ? C4 H4A 0.9300 . ? C5 C6 1.469(6) . ? C6 C7 1.331(7) . ? C6 H6A 0.9300 . ? C7 C8 1.452(6) . ? C7 H7A 0.9300 . ? C8 N3 1.348(6) . ? C8 C9 1.390(8) . ? C9 C10 1.360(7) . ? C9 H9A 0.9300 . ? C10 N2 1.333(7) . ? C10 H10A 0.9300 . ? C11 N2 1.330(7) . ? C11 N3 1.330(6) . ? C11 H11A 0.9300 . ? N4 O3 1.176(7) . ? N4 O5 1.184(6) . ? N4 O4 1.204(6) . ? O1 H2W 0.84(3) . ? O1 H1W 0.82(3) . ? O2 H4W 0.81(3) . ? O2 H3W 0.84(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 O2 Cu1 O2 180.0 3_565 . ? O2 Cu1 N1 88.56(16) 3_565 . ? O2 Cu1 N1 91.44(16) . . ? O2 Cu1 N1 91.44(16) 3_565 3_565 ? O2 Cu1 N1 88.56(16) . 3_565 ? N1 Cu1 N1 180.00(8) . 3_565 ? O2 Cu1 O1 89.79(16) 3_565 . ? O2 Cu1 O1 90.21(16) . . ? N1 Cu1 O1 90.56(16) . . ? N1 Cu1 O1 89.44(16) 3_565 . ? O2 Cu1 O1 90.21(16) 3_565 3_565 ? O2 Cu1 O1 89.79(16) . 3_565 ? N1 Cu1 O1 89.44(16) . 3_565 ? N1 Cu1 O1 90.56(16) 3_565 3_565 ? O1 Cu1 O1 180.0 . 3_565 ? N1 C1 C5 123.9(5) . . ? N1 C1 H1A 118.0 . . ? C5 C1 H1A 118.0 . . ? N1 C2 C3 122.3(5) . . ? N1 C2 H2A 118.8 . . ? C3 C2 H2A 118.8 . . ? C2 C3 C4 119.7(5) . . ? C2 C3 H3A 120.1 . . ? C4 C3 H3A 120.1 . . ? C3 C4 C5 119.2(5) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? C1 C5 C4 117.5(5) . . ? C1 C5 C6 117.9(5) . . ? C4 C5 C6 124.6(5) . . ? C7 C6 C5 127.1(5) . . ? C7 C6 H6A 116.5 . . ? C5 C6 H6A 116.5 . . ? C6 C7 C8 123.0(5) . . ? C6 C7 H7A 118.5 . . ? C8 C7 H7A 118.5 . . ? N3 C8 C9 119.7(5) . . ? N3 C8 C7 116.6(5) . . ? C9 C8 C7 123.7(5) . . ? C10 C9 C8 118.0(6) . . ? C10 C9 H9A 121.0 . . ? C8 C9 H9A 121.0 . . ? N2 C10 C9 123.6(6) . . ? N2 C10 H10A 118.2 . . ? C9 C10 H10A 118.2 . . ? N2 C11 N3 127.7(6) . . ? N2 C11 H11A 116.1 . . ? N3 C11 H11A 116.1 . . ? C1 N1 C2 117.3(5) . . ? C1 N1 Cu1 121.1(4) . . ? C2 N1 Cu1 121.6(3) . . ? C11 N3 C8 116.7(5) . . ? C11 N2 C10 114.3(5) . . ? O3 N4 O5 116.8(6) . . ? O3 N4 O4 118.9(5) . . ? O5 N4 O4 123.7(6) . . ? Cu1 O1 H2W 123(4) . . ? Cu1 O1 H1W 125(4) . . ? H2W O1 H1W 112(4) . . ? Cu1 O2 H4W 117(4) . . ? Cu1 O2 H3W 115(4) . . ? H4W O2 H3W 113(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 C2 C3 C4 1.1(9) . . . . ? C2 C3 C4 C5 0.2(9) . . . . ? N1 C1 C5 C4 -0.2(8) . . . . ? N1 C1 C5 C6 -179.1(5) . . . . ? C3 C4 C5 C1 -0.6(8) . . . . ? C3 C4 C5 C6 178.2(5) . . . . ? C1 C5 C6 C7 -167.1(6) . . . . ? C4 C5 C6 C7 14.1(9) . . . . ? C5 C6 C7 C8 177.8(5) . . . . ? C6 C7 C8 N3 -161.7(5) . . . . ? C6 C7 C8 C9 18.1(9) . . . . ? N3 C8 C9 C10 1.4(9) . . . . ? C7 C8 C9 C10 -178.4(5) . . . . ? C8 C9 C10 N2 0.1(10) . . . . ? C5 C1 N1 C2 1.4(8) . . . . ? C5 C1 N1 Cu1 -179.1(4) . . . . ? C3 C2 N1 C1 -1.9(8) . . . . ? C3 C2 N1 Cu1 178.7(4) . . . . ? O2 Cu1 N1 C1 -131.7(4) 3_565 . . . ? O2 Cu1 N1 C1 48.3(4) . . . . ? N1 Cu1 N1 C1 -175(28) 3_565 . . . ? O1 Cu1 N1 C1 -41.9(4) . . . . ? O1 Cu1 N1 C1 138.1(4) 3_565 . . . ? O2 Cu1 N1 C2 47.8(4) 3_565 . . . ? O2 Cu1 N1 C2 -132.2(4) . . . . ? N1 Cu1 N1 C2 4(28) 3_565 . . . ? O1 Cu1 N1 C2 137.5(4) . . . . ? O1 Cu1 N1 C2 -42.5(4) 3_565 . . . ? N2 C11 N3 C8 1.7(9) . . . . ? C9 C8 N3 C11 -2.1(8) . . . . ? C7 C8 N3 C11 177.7(5) . . . . ? N3 C11 N2 C10 -0.4(9) . . . . ? C9 C10 N2 C11 -0.6(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H2W N3 0.84(3) 2.10(4) 2.907(6) 160(6) 1_554 O1 H1W O5 0.82(3) 2.05(3) 2.873(6) 175(6) 2 O2 H4W N2 0.81(3) 1.99(3) 2.786(5) 166(5) 3_666 O2 H3W O4 0.84(3) 1.89(3) 2.727(6) 178(5) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.583 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.076 # Attachment '7.cif' data_7 _database_code_depnum_ccdc_archive 'CCDC 662568' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H23 Cu N3 O11 S' _chemical_formula_weight 468.92 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' S S 0.1246 0.1234 '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' _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 23.348(2) _cell_length_b 7.2939(7) _cell_length_c 22.706(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.5430(10) _cell_angle_gamma 90.00 _cell_volume 3824.0(6) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4171 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 27.47 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1944 _exptl_absorpt_coefficient_mu 1.312 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6944 _exptl_absorpt_correction_T_max 0.7794 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9462 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3358 _reflns_number_gt 2911 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0494P)^2^+2.5752P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3358 _refine_ls_number_parameters 303 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0372 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0863 _refine_ls_wR_factor_gt 0.0830 _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 Cu1 Cu 0.5000 0.5000 0.5000 0.02558(13) Uani 1 2 d S . . Cu2 Cu 0.0000 0.45627(5) 0.2500 0.02314(13) Uani 1 2 d S . . C1 C 0.37326(10) 0.4937(3) 0.48528(11) 0.0318(6) Uani 1 1 d . . . H1A H 0.3780 0.4842 0.4455 0.038 Uiso 1 1 calc R . . C2 C 0.41354(11) 0.5158(4) 0.58336(11) 0.0339(6) Uani 1 1 d . . . H2A H 0.4462 0.5218 0.6122 0.041 Uiso 1 1 calc R . . C3 C 0.35981(11) 0.5204(4) 0.60102(12) 0.0385(6) Uani 1 1 d . . . H3A H 0.3563 0.5297 0.6412 0.046 Uiso 1 1 calc R . . C4 C 0.31109(11) 0.5111(4) 0.55856(12) 0.0389(6) Uani 1 1 d . . . H4A H 0.2744 0.5140 0.5699 0.047 Uiso 1 1 calc R . . C5 C 0.31709(10) 0.4973(3) 0.49876(11) 0.0320(6) Uani 1 1 d . . . C6 C 0.26935(11) 0.4858(4) 0.44975(12) 0.0386(6) Uani 1 1 d . . . H6A H 0.2792 0.4787 0.4116 0.046 Uiso 1 1 calc R . . C7 C 0.21367(11) 0.4842(4) 0.45391(12) 0.0371(6) Uani 1 1 d . . . H7A H 0.2032 0.4914 0.4918 0.045 Uiso 1 1 calc R . . C8 C 0.16719(10) 0.4721(4) 0.40334(11) 0.0339(6) Uani 1 1 d . . . C9 C 0.17552(12) 0.4385(5) 0.34539(13) 0.0569(9) Uani 1 1 d . . . H9A H 0.2126 0.4215 0.3359 0.068 Uiso 1 1 calc R . . C10 C 0.12821(12) 0.4307(5) 0.30229(13) 0.0592(9) Uani 1 1 d . . . H10A H 0.1336 0.4062 0.2633 0.071 Uiso 1 1 calc R . . C11 C 0.07002(11) 0.4842(4) 0.37062(12) 0.0371(6) Uani 1 1 d . . . H11A H 0.0328 0.4990 0.3800 0.045 Uiso 1 1 calc R . . N1 N 0.42059(8) 0.5029(3) 0.52580(9) 0.0293(5) Uani 1 1 d . . . N2 N 0.07412(8) 0.4572(3) 0.31396(9) 0.0322(5) Uani 1 1 d . . . N3 N 0.11318(9) 0.4925(3) 0.41571(10) 0.0373(5) Uani 1 1 d . . . O1 O 0.52412(7) 0.3114(3) 0.56336(8) 0.0340(4) Uani 1 1 d D . . H1WB H 0.5412(11) 0.227(3) 0.5514(12) 0.042(9) Uiso 1 1 d D . . H1WA H 0.5418(12) 0.344(4) 0.5968(10) 0.051(9) Uiso 1 1 d D . . O2 O 0.52473(8) 0.7344(3) 0.56637(9) 0.0412(5) Uani 1 1 d D . . H2WB H 0.5366(11) 0.825(3) 0.5527(11) 0.039(8) Uiso 1 1 d D . . H2WA H 0.5440(13) 0.714(5) 0.5995(11) 0.068(11) Uiso 1 1 d D . . O3 O -0.05901(8) 0.4625(3) 0.32228(8) 0.0350(4) Uani 1 1 d D . . H3WB H -0.0771(10) 0.373(3) 0.3266(11) 0.034(8) Uiso 1 1 d D . . H3WA H -0.0789(12) 0.555(3) 0.3271(14) 0.050(10) Uiso 1 1 d D . . O4 O 0.0000 0.1898(4) 0.2500 0.0600(9) Uani 1 2 d SD . . H4WA H 0.0290(8) 0.129(4) 0.2507(15) 0.066(11) Uiso 1 1 d D . . O5 O 0.0000 0.7235(4) 0.2500 0.0607(9) Uani 1 2 d SD . . H5WA H 0.0287(8) 0.786(4) 0.2501(15) 0.065(11) Uiso 1 1 d D . . O6 O 0.73497(14) 0.8226(4) 0.19283(15) 0.1038(12) Uani 1 1 d D . . H6WB H 0.7593(17) 0.871(6) 0.2184(17) 0.119(17) Uiso 1 1 d D . . H6WA H 0.7230(16) 0.723(4) 0.2059(16) 0.093(15) Uiso 1 1 d D . . O7 O 0.08531(9) 0.5315(3) 0.53070(10) 0.0425(5) Uani 1 1 d D . . H7WB H 0.0905(14) 0.527(4) 0.4963(11) 0.050(10) Uiso 1 1 d D . . H7WA H 0.1157(12) 0.521(4) 0.5535(13) 0.061(11) Uiso 1 1 d D . . O8 O 0.18176(10) 0.5518(4) 0.10980(11) 0.0586(6) Uani 1 1 d D . . H8WB H 0.1696(14) 0.635(4) 0.1314(14) 0.071(12) Uiso 1 1 d D . . H8WA H 0.1917(18) 0.464(4) 0.1342(16) 0.088(15) Uiso 1 1 d D . . O9 O 0.08987(9) 0.9551(3) 0.24974(9) 0.0529(6) Uani 1 1 d . . . O10 O 0.11361(9) 0.7953(3) 0.16400(9) 0.0523(5) Uani 1 1 d . . . O11 O 0.10267(9) 1.1204(3) 0.16067(8) 0.0510(5) Uani 1 1 d . . . O12 O 0.18416(9) 0.9861(3) 0.22063(11) 0.0618(7) Uani 1 1 d . . . S1 S 0.12267(3) 0.96380(8) 0.19953(3) 0.02858(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0160(2) 0.0360(3) 0.0237(2) 0.00232(16) -0.00074(16) 0.00006(16) Cu2 0.0191(2) 0.0232(2) 0.0256(2) 0.000 -0.00179(15) 0.000 C1 0.0236(13) 0.0470(15) 0.0248(13) -0.0009(10) 0.0034(10) -0.0004(10) C2 0.0264(13) 0.0477(16) 0.0256(13) 0.0001(11) -0.0029(10) -0.0029(11) C3 0.0326(15) 0.0581(18) 0.0253(13) -0.0015(11) 0.0059(11) -0.0037(12) C4 0.0200(13) 0.0617(18) 0.0359(15) 0.0003(12) 0.0076(11) 0.0001(11) C5 0.0209(12) 0.0440(15) 0.0302(13) 0.0011(10) 0.0010(10) 0.0006(10) C6 0.0229(13) 0.0626(18) 0.0295(14) -0.0009(12) 0.0011(10) 0.0001(12) C7 0.0229(13) 0.0595(18) 0.0278(14) -0.0030(12) 0.0001(10) 0.0003(11) C8 0.0222(13) 0.0455(16) 0.0330(14) -0.0001(11) 0.0002(10) 0.0001(10) C9 0.0218(14) 0.112(3) 0.0361(16) -0.0060(17) 0.0021(11) 0.0067(15) C10 0.0313(16) 0.114(3) 0.0323(16) -0.0050(17) 0.0032(12) 0.0093(17) C11 0.0196(12) 0.0574(18) 0.0337(15) -0.0047(12) 0.0021(10) 0.0016(11) N1 0.0193(10) 0.0407(12) 0.0267(11) 0.0018(8) 0.0000(8) -0.0007(8) N2 0.0214(11) 0.0469(13) 0.0275(11) -0.0002(9) 0.0011(8) 0.0003(9) N3 0.0201(11) 0.0625(15) 0.0289(12) -0.0060(10) 0.0024(9) 0.0007(9) O1 0.0308(9) 0.0399(11) 0.0301(10) 0.0008(8) 0.0002(8) 0.0047(8) O2 0.0392(11) 0.0453(12) 0.0379(11) -0.0031(9) 0.0018(9) -0.0098(9) O3 0.0286(10) 0.0400(12) 0.0362(10) -0.0010(8) 0.0037(8) -0.0007(9) O4 0.0310(16) 0.0238(15) 0.129(3) 0.000 0.0255(18) 0.000 O5 0.0319(16) 0.0215(14) 0.132(3) 0.000 0.0220(18) 0.000 O6 0.104(2) 0.076(2) 0.110(2) 0.0313(18) -0.0534(19) -0.0423(18) O7 0.0447(13) 0.0516(13) 0.0318(11) 0.0001(9) 0.0075(10) 0.0037(9) O8 0.0485(14) 0.0785(18) 0.0492(14) -0.0019(13) 0.0088(11) 0.0095(12) O9 0.0530(13) 0.0665(14) 0.0401(12) -0.0030(10) 0.0101(10) -0.0060(10) O10 0.0618(13) 0.0365(11) 0.0586(13) -0.0114(9) 0.0085(10) -0.0015(9) O11 0.0603(13) 0.0392(11) 0.0478(12) 0.0039(9) -0.0107(9) 0.0112(10) O12 0.0286(11) 0.0698(15) 0.0816(17) 0.0211(12) -0.0092(11) -0.0044(9) S1 0.0237(3) 0.0309(3) 0.0295(3) -0.0009(2) -0.0017(2) 0.0005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 2.0099(17) 5_666 ? Cu1 O1 2.0099(17) . ? Cu1 N1 2.026(2) . ? Cu1 N1 2.026(2) 5_666 ? Cu1 O2 2.2953(19) 5_666 ? Cu1 O2 2.2953(19) . ? Cu2 O4 1.944(3) . ? Cu2 O5 1.949(3) . ? Cu2 N2 2.0874(19) 6_556 ? Cu2 N2 2.0874(19) . ? Cu2 O3 2.2946(19) . ? Cu2 O3 2.2946(19) 6_556 ? C1 N1 1.330(3) . ? C1 C5 1.391(3) . ? C1 H1A 0.9300 . ? C2 N1 1.345(3) . ? C2 C3 1.373(4) . ? C2 H2A 0.9300 . ? C3 C4 1.379(4) . ? C3 H3A 0.9300 . ? C4 C5 1.389(4) . ? C4 H4A 0.9300 . ? C5 C6 1.456(4) . ? C6 C7 1.317(4) . ? C6 H6A 0.9300 . ? C7 C8 1.461(4) . ? C7 H7A 0.9300 . ? C8 N3 1.341(3) . ? C8 C9 1.380(4) . ? C9 C10 1.364(4) . ? C9 H9A 0.9300 . ? C10 N2 1.342(3) . ? C10 H10A 0.9300 . ? C11 N2 1.319(3) . ? C11 N3 1.327(3) . ? C11 H11A 0.9300 . ? O1 H1WB 0.80(2) . ? O1 H1WA 0.84(2) . ? O2 H2WB 0.80(2) . ? O2 H2WA 0.83(2) . ? O3 H3WB 0.79(2) . ? O3 H3WA 0.83(2) . ? O4 H4WA 0.808(17) . ? O5 H5WA 0.811(17) . ? O6 H6WB 0.83(3) . ? O6 H6WA 0.85(2) . ? O7 H7WB 0.81(2) . ? O7 H7WA 0.82(2) . ? O8 H8WB 0.86(2) . ? O8 H8WA 0.86(2) . ? O9 S1 1.466(2) . ? O10 S1 1.4684(19) . ? O11 S1 1.4759(19) . ? O12 S1 1.454(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 Cu1 O1 180.00(8) 5_666 . ? O1 Cu1 N1 91.64(8) 5_666 . ? O1 Cu1 N1 88.36(8) . . ? O1 Cu1 N1 88.36(8) 5_666 5_666 ? O1 Cu1 N1 91.64(8) . 5_666 ? N1 Cu1 N1 180.0 . 5_666 ? O1 Cu1 O2 91.35(8) 5_666 5_666 ? O1 Cu1 O2 88.65(8) . 5_666 ? N1 Cu1 O2 92.63(8) . 5_666 ? N1 Cu1 O2 87.37(8) 5_666 5_666 ? O1 Cu1 O2 88.65(8) 5_666 . ? O1 Cu1 O2 91.35(8) . . ? N1 Cu1 O2 87.37(8) . . ? N1 Cu1 O2 92.63(8) 5_666 . ? O2 Cu1 O2 180.000(1) 5_666 . ? O4 Cu2 O5 180.000(1) . . ? O4 Cu2 N2 90.19(6) . 6_556 ? O5 Cu2 N2 89.81(6) . 6_556 ? O4 Cu2 N2 90.19(6) . . ? O5 Cu2 N2 89.81(6) . . ? N2 Cu2 N2 179.62(12) 6_556 . ? O4 Cu2 O3 91.13(5) . . ? O5 Cu2 O3 88.87(5) . . ? N2 Cu2 O3 88.49(7) 6_556 . ? N2 Cu2 O3 91.50(7) . . ? O4 Cu2 O3 91.13(5) . 6_556 ? O5 Cu2 O3 88.87(5) . 6_556 ? N2 Cu2 O3 91.50(7) 6_556 6_556 ? N2 Cu2 O3 88.49(7) . 6_556 ? O3 Cu2 O3 177.74(11) . 6_556 ? N1 C1 C5 124.1(2) . . ? N1 C1 H1A 118.0 . . ? C5 C1 H1A 118.0 . . ? N1 C2 C3 122.3(2) . . ? N1 C2 H2A 118.8 . . ? C3 C2 H2A 118.8 . . ? C2 C3 C4 119.3(2) . . ? C2 C3 H3A 120.4 . . ? C4 C3 H3A 120.4 . . ? C3 C4 C5 119.6(2) . . ? C3 C4 H4A 120.2 . . ? C5 C4 H4A 120.2 . . ? C4 C5 C1 116.9(2) . . ? C4 C5 C6 125.1(2) . . ? C1 C5 C6 118.1(2) . . ? C7 C6 C5 126.7(3) . . ? C7 C6 H6A 116.7 . . ? C5 C6 H6A 116.7 . . ? C6 C7 C8 124.7(3) . . ? C6 C7 H7A 117.6 . . ? C8 C7 H7A 117.6 . . ? N3 C8 C9 119.3(2) . . ? N3 C8 C7 116.1(2) . . ? C9 C8 C7 124.5(2) . . ? C10 C9 C8 118.5(3) . . ? C10 C9 H9A 120.7 . . ? C8 C9 H9A 120.7 . . ? N2 C10 C9 122.5(3) . . ? N2 C10 H10A 118.7 . . ? C9 C10 H10A 118.7 . . ? N2 C11 N3 127.1(2) . . ? N2 C11 H11A 116.5 . . ? N3 C11 H11A 116.5 . . ? C1 N1 C2 117.8(2) . . ? C1 N1 Cu1 120.09(16) . . ? C2 N1 Cu1 122.09(16) . . ? C11 N2 C10 114.9(2) . . ? C11 N2 Cu2 120.42(16) . . ? C10 N2 Cu2 124.71(18) . . ? C11 N3 C8 117.6(2) . . ? Cu1 O1 H1WB 113(2) . . ? Cu1 O1 H1WA 120(2) . . ? H1WB O1 H1WA 109(3) . . ? Cu1 O2 H2WB 116(2) . . ? Cu1 O2 H2WA 121(2) . . ? H2WB O2 H2WA 109(3) . . ? Cu2 O3 H3WB 117.4(19) . . ? Cu2 O3 H3WA 121(2) . . ? H3WB O3 H3WA 109(3) . . ? Cu2 O4 H4WA 123(2) . . ? Cu2 O5 H5WA 124(2) . . ? H6WB O6 H6WA 110(4) . . ? H7WB O7 H7WA 111(3) . . ? H8WB O8 H8WA 104(3) . . ? O12 S1 O9 110.67(14) . . ? O12 S1 O10 109.24(13) . . ? O9 S1 O10 109.98(12) . . ? O12 S1 O11 108.64(12) . . ? O9 S1 O11 110.06(12) . . ? O10 S1 O11 108.20(12) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1WB O7 0.80(2) 1.86(2) 2.660(3) 175(3) 3_545 O1 H1WA O11 0.84(2) 1.89(2) 2.700(2) 160(3) 4_565 O2 H2WB O7 0.80(2) 1.99(2) 2.774(3) 165(3) 3 O2 H2WA O10 0.83(2) 2.02(2) 2.811(3) 159(3) 4_565 O3 H3WB O11 0.79(2) 1.97(2) 2.745(3) 165(3) 6_546 O3 H3WA O10 0.83(2) 1.96(2) 2.781(3) 170(3) 6_556 O4 H4WA O9 0.808(17) 1.907(19) 2.709(3) 172(3) 1_545 O5 H5WA O9 0.811(17) 1.886(18) 2.694(3) 174(3) . O6 H6WB O12 0.83(3) 1.95(3) 2.783(4) 179(5) 6_656 O6 H6WA O12 0.85(2) 2.00(3) 2.838(4) 168(4) 3_545 O7 H7WB N3 0.81(2) 1.99(2) 2.797(3) 172(3) . O7 H7WA O8 0.82(2) 1.93(2) 2.732(3) 169(3) 2_565 O8 H8WB O10 0.86(2) 1.98(3) 2.790(3) 158(3) . O8 H8WA O6 0.86(2) 1.86(3) 2.683(4) 161(4) 3_445 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.551 _refine_diff_density_min -0.460 _refine_diff_density_rms 0.077