# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address M.Mondal ;Indian Institute of Technology Guwahati, Assam-781039 ; A.kalita '' 'Pankaj Kumar' '' _publ_contact_author_address ;Indian Institute of Technology Guwahati, Assam-781039 ; _publ_contact_author_email biplab@iitg.ernet.in #TrackingRef '8924_web_deposit_cif_file_0_Dr.BiplabMondal_1325827290.CIF of complex 2.cif' _publ_contact_author_name 'Dr. Biplab Mondal' data_tp1 _database_code_depnum_ccdc_archive 'CCDC 861293' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H36 Cu N9 O7' _chemical_compound_source Synthesised _exptl_crystal_recrystallization_method acetonitrile _chemical_melting_point ? _exptl_crystal_description cube _exptl_crystal_colour yellow _diffrn_ambient_temperature 296(2) _chemical_formula_weight 650.19 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' Cu Cu 0.3201 1.2651 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2/c' _symmetry_int_tables_number 13 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 9.3665(10) _cell_length_b 9.6913(11) _cell_length_c 18.1622(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.203(5) _cell_angle_gamma 90.00 _cell_volume 1648.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9850 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 32.84 _exptl_crystal_size_max 0.038 _exptl_crystal_size_mid 0.028 _exptl_crystal_size_min 0.020 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680.0 _exptl_absorpt_coefficient_mu 0.716 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32078 _diffrn_reflns_av_R_equivalents 0.1032 _diffrn_reflns_av_sigmaI/netI 0.0601 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 35.54 _reflns_number_total 7344 _reflns_number_gt 5057 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1496P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7344 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0838 _refine_ls_R_factor_gt 0.0664 _refine_ls_wR_factor_ref 0.2274 _refine_ls_wR_factor_gt 0.2162 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 0.30446(3) 0.2500 0.02539(13) Uani 1 2 d S . . O1 O 0.3930(2) 0.5249(3) 0.23025(12) 0.0575(5) Uani 1 1 d . . . O2 O 0.5000 0.7179(3) 0.2500 0.0766(12) Uani 1 2 d S . . N2 N 0.2377(2) -0.0369(2) 0.19162(11) 0.0369(4) Uani 1 1 d . . . N1 N 0.34389(19) 0.1600(2) 0.21464(9) 0.0296(3) Uani 1 1 d . . . N3 N 0.56833(18) 0.32449(18) 0.14728(9) 0.0277(3) Uani 1 1 d . . . N4 N 0.7007(2) 0.3484(2) 0.04858(10) 0.0383(4) Uani 1 1 d . . . N5 N 0.5000 0.5949(3) 0.2500 0.0423(6) Uani 1 2 d S . . C2 C 0.3336(3) -0.0101(3) 0.31962(13) 0.0436(5) Uani 1 1 d . . . H2A H 0.3385 0.0689 0.3523 0.052 Uiso 1 1 calc R . . H2B H 0.4258 -0.0554 0.3208 0.052 Uiso 1 1 calc R . . C3 C 0.3058(2) 0.0401(2) 0.24312(11) 0.0321(4) Uani 1 1 d . . . C4 C 0.2331(2) 0.0372(3) 0.12653(12) 0.0347(4) Uani 1 1 d . . . C6 C 0.2983(2) 0.1593(2) 0.14143(11) 0.0292(4) Uani 1 1 d . . . C7 C 0.3268(2) 0.2805(2) 0.09261(12) 0.0340(4) Uani 1 1 d . . . H7A H 0.2860 0.2633 0.0443 0.041 Uiso 1 1 calc R . . H7B H 0.2807 0.3616 0.1129 0.041 Uiso 1 1 calc R . . C5 C 0.1661(3) -0.0171(3) 0.05822(16) 0.0546(7) Uani 1 1 d . . . H5A H 0.1308 0.0583 0.0292 0.082 Uiso 1 1 calc R . . H5B H 0.0885 -0.0772 0.0708 0.082 Uiso 1 1 calc R . . H5C H 0.2358 -0.0676 0.0305 0.082 Uiso 1 1 calc R . . C8 C 0.4822(2) 0.3076(2) 0.08508(11) 0.0291(4) Uani 1 1 d . . . C9 C 0.5629(3) 0.3216(3) 0.02392(12) 0.0368(5) Uani 1 1 d . . . C10 C 0.5281(4) 0.3141(3) -0.05648(14) 0.0561(8) Uani 1 1 d . . . H10A H 0.4850 0.2265 -0.0673 0.084 Uiso 1 1 calc R . . H10B H 0.6141 0.3242 -0.0846 0.084 Uiso 1 1 calc R . . H10C H 0.4628 0.3868 -0.0691 0.084 Uiso 1 1 calc R . . C11 C 0.6995(2) 0.3505(2) 0.12281(11) 0.0313(4) Uani 1 1 d . . . C12 C 0.8300(2) 0.3780(3) 0.16760(13) 0.0410(5) Uani 1 1 d . . . H12A H 0.8055 0.3715 0.2193 0.049 Uiso 1 1 calc R . . H12B H 0.8614 0.4718 0.1583 0.049 Uiso 1 1 calc R . . C13 C 0.9521(3) 0.2814(5) 0.1524(2) 0.0675(10) Uani 1 1 d . . . H13A H 0.9282 0.1905 0.1693 0.101 Uiso 1 1 calc R . . H13B H 1.0360 0.3133 0.1777 0.101 Uiso 1 1 calc R . . H13C H 0.9702 0.2788 0.1004 0.101 Uiso 1 1 calc R . . C1 C 0.2224(4) -0.1089(4) 0.34830(16) 0.0645(9) Uani 1 1 d . . . H1A H 0.1289 -0.0712 0.3398 0.097 Uiso 1 1 calc R . . H1B H 0.2365 -0.1226 0.4002 0.097 Uiso 1 1 calc R . . H1C H 0.2308 -0.1956 0.3232 0.097 Uiso 1 1 calc R . . O3 O 0.1220(3) 0.6789(2) 0.20011(13) 0.0562(5) Uani 1 1 d . . . O4 O 0.98143(18) 0.37225(17) -0.04386(7) 0.0370(4) 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 0.02307(17) 0.0322(2) 0.02086(17) 0.000 0.00111(11) 0.000 O1 0.0517(11) 0.0729(15) 0.0478(11) -0.0018(10) 0.0049(9) -0.0165(10) O2 0.123(3) 0.0317(16) 0.075(2) 0.000 0.014(2) 0.000 N2 0.0415(10) 0.0360(10) 0.0332(8) 0.0019(7) -0.0014(7) -0.0064(8) N1 0.0307(7) 0.0340(9) 0.0241(7) 0.0007(6) -0.0012(6) -0.0025(7) N3 0.0238(7) 0.0354(9) 0.0240(7) 0.0002(6) 0.0018(5) 0.0000(6) N4 0.0379(9) 0.0493(12) 0.0279(8) -0.0003(8) 0.0084(7) -0.0080(8) N5 0.0518(16) 0.0377(16) 0.0374(13) 0.000 0.0108(12) 0.000 C2 0.0605(15) 0.0397(13) 0.0305(10) 0.0086(9) -0.0033(9) -0.0056(11) C3 0.0357(9) 0.0337(11) 0.0268(8) 0.0002(7) 0.0004(7) -0.0027(8) C4 0.0319(9) 0.0422(12) 0.0299(9) -0.0010(8) -0.0039(7) -0.0061(8) C6 0.0243(8) 0.0361(10) 0.0272(8) 0.0032(7) -0.0019(6) -0.0016(7) C7 0.0271(8) 0.0433(12) 0.0314(9) 0.0073(8) -0.0063(7) -0.0021(8) C5 0.0622(16) 0.0595(18) 0.0421(13) -0.0026(12) -0.0166(12) -0.0181(14) C8 0.0299(8) 0.0338(11) 0.0235(8) 0.0022(6) -0.0014(6) -0.0023(7) C9 0.0436(11) 0.0427(13) 0.0240(9) -0.0003(7) 0.0028(8) -0.0059(9) C10 0.072(2) 0.071(2) 0.0254(10) 0.0022(10) -0.0007(11) -0.0150(14) C11 0.0279(8) 0.0369(11) 0.0293(8) -0.0007(7) 0.0058(7) -0.0030(8) C12 0.0251(8) 0.0574(16) 0.0405(11) -0.0037(10) 0.0034(8) -0.0065(9) C13 0.0331(12) 0.106(3) 0.0638(19) -0.0057(18) 0.0026(13) 0.0195(15) C1 0.075(2) 0.078(2) 0.0402(13) 0.0180(14) 0.0068(13) -0.0172(17) O3 0.0669(14) 0.0556(13) 0.0461(11) 0.0008(8) 0.0008(10) -0.0069(9) O4 0.0539(9) 0.0413(9) 0.0159(5) -0.0101(5) 0.0172(5) -0.0159(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 Cu1 N3 1.9840(16) . ? Cu1 N3 1.9841(16) 2_655 ? Cu1 N1 2.1222(18) 2_655 ? Cu1 N1 2.1222(18) . ? Cu1 O1 2.386(3) . ? Cu1 O1 2.386(3) 2_655 ? O1 N5 1.261(3) . ? O2 N5 1.193(4) . ? N2 C3 1.354(3) . ? N2 C4 1.384(3) . ? N1 C3 1.322(3) . ? N1 C6 1.395(3) . ? N3 C11 1.332(2) . ? N3 C8 1.395(3) . ? N4 C11 1.348(3) . ? N4 C9 1.389(3) . ? N5 O1 1.261(3) 2_655 ? C2 C3 1.494(3) . ? C2 C1 1.509(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C4 C6 1.359(3) . ? C4 C5 1.485(3) . ? C6 C7 1.496(3) . ? C7 C8 1.486(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C8 C9 1.353(3) . ? C9 C10 1.497(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.490(3) . ? C12 C13 1.504(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cu1 N3 168.77(10) . 2_655 ? N3 Cu1 N1 97.18(7) . 2_655 ? N3 Cu1 N1 90.24(7) 2_655 2_655 ? N3 Cu1 N1 90.24(7) . . ? N3 Cu1 N1 97.18(7) 2_655 . ? N1 Cu1 N1 97.45(10) 2_655 . ? N3 Cu1 O1 84.70(7) . . ? N3 Cu1 O1 85.24(7) 2_655 . ? N1 Cu1 O1 157.61(8) 2_655 . ? N1 Cu1 O1 104.86(7) . . ? N3 Cu1 O1 85.24(7) . 2_655 ? N3 Cu1 O1 84.70(7) 2_655 2_655 ? N1 Cu1 O1 104.87(7) 2_655 2_655 ? N1 Cu1 O1 157.61(8) . 2_655 ? O1 Cu1 O1 52.92(10) . 2_655 ? N5 O1 Cu1 96.09(18) . . ? C3 N2 C4 108.52(19) . . ? C3 N1 C6 106.67(17) . . ? C3 N1 Cu1 130.40(14) . . ? C6 N1 Cu1 119.98(14) . . ? C11 N3 C8 106.46(17) . . ? C11 N3 Cu1 129.29(14) . . ? C8 N3 Cu1 124.21(14) . . ? C11 N4 C9 108.30(17) . . ? O2 N5 O1 122.55(17) . . ? O2 N5 O1 122.55(17) . 2_655 ? O1 N5 O1 114.9(3) . 2_655 ? C3 C2 C1 114.2(2) . . ? C3 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? N1 C3 N2 109.95(18) . . ? N1 C3 C2 127.2(2) . . ? N2 C3 C2 122.9(2) . . ? C6 C4 N2 105.60(18) . . ? C6 C4 C5 131.6(2) . . ? N2 C4 C5 122.8(2) . . ? C4 C6 N1 109.26(18) . . ? C4 C6 C7 130.30(19) . . ? N1 C6 C7 120.43(19) . . ? C8 C7 C6 111.70(17) . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C9 C8 N3 109.25(19) . . ? C9 C8 C7 130.1(2) . . ? N3 C8 C7 120.66(18) . . ? C8 C9 N4 106.00(19) . . ? C8 C9 C10 132.5(3) . . ? N4 C9 C10 121.5(2) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 N4 109.99(18) . . ? N3 C11 C12 127.42(19) . . ? N4 C11 C12 122.59(18) . . ? C11 C12 C13 114.3(2) . . ? C11 C12 H12A 108.7 . . ? C13 C12 H12A 108.7 . . ? C11 C12 H12B 108.7 . . ? C13 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Cu1 O1 N5 -88.03(12) . . . . ? N3 Cu1 O1 N5 86.95(12) 2_655 . . . ? N1 Cu1 O1 N5 8.0(3) 2_655 . . . ? N1 Cu1 O1 N5 -176.87(10) . . . . ? O1 Cu1 O1 N5 0.0 2_655 . . . ? N3 Cu1 N1 C3 135.15(19) . . . . ? N3 Cu1 N1 C3 -53.3(2) 2_655 . . . ? N1 Cu1 N1 C3 37.88(17) 2_655 . . . ? O1 Cu1 N1 C3 -140.26(19) . . . . ? O1 Cu1 N1 C3 -146.8(2) 2_655 . . . ? N3 Cu1 N1 C6 -22.66(16) . . . . ? N3 Cu1 N1 C6 148.88(16) 2_655 . . . ? N1 Cu1 N1 C6 -119.93(18) 2_655 . . . ? O1 Cu1 N1 C6 61.93(17) . . . . ? O1 Cu1 N1 C6 55.4(3) 2_655 . . . ? N3 Cu1 N3 C11 80.48(19) 2_655 . . . ? N1 Cu1 N3 C11 -50.5(2) 2_655 . . . ? N1 Cu1 N3 C11 -148.0(2) . . . . ? O1 Cu1 N3 C11 107.1(2) . . . . ? O1 Cu1 N3 C11 53.9(2) 2_655 . . . ? N3 Cu1 N3 C8 -102.11(15) 2_655 . . . ? N1 Cu1 N3 C8 126.93(16) 2_655 . . . ? N1 Cu1 N3 C8 29.39(16) . . . . ? O1 Cu1 N3 C8 -75.52(16) . . . . ? O1 Cu1 N3 C8 -128.65(16) 2_655 . . . ? Cu1 O1 N5 O2 180.0 . . . . ? Cu1 O1 N5 O1 0.0 . . . 2_655 ? C6 N1 C3 N2 -0.2(2) . . . . ? Cu1 N1 C3 N2 -160.22(16) . . . . ? C6 N1 C3 C2 178.5(2) . . . . ? Cu1 N1 C3 C2 18.5(3) . . . . ? C4 N2 C3 N1 0.5(3) . . . . ? C4 N2 C3 C2 -178.2(2) . . . . ? C1 C2 C3 N1 150.6(3) . . . . ? C1 C2 C3 N2 -30.9(4) . . . . ? C3 N2 C4 C6 -0.7(3) . . . . ? C3 N2 C4 C5 179.8(2) . . . . ? N2 C4 C6 N1 0.5(2) . . . . ? C5 C4 C6 N1 -179.9(3) . . . . ? N2 C4 C6 C7 179.3(2) . . . . ? C5 C4 C6 C7 -1.1(4) . . . . ? C3 N1 C6 C4 -0.2(2) . . . . ? Cu1 N1 C6 C4 162.30(15) . . . . ? C3 N1 C6 C7 -179.15(19) . . . . ? Cu1 N1 C6 C7 -16.6(3) . . . . ? C4 C6 C7 C8 -118.3(2) . . . . ? N1 C6 C7 C8 60.3(3) . . . . ? C11 N3 C8 C9 0.9(2) . . . . ? Cu1 N3 C8 C9 -177.04(16) . . . . ? C11 N3 C8 C7 -178.4(2) . . . . ? Cu1 N3 C8 C7 3.7(3) . . . . ? C6 C7 C8 C9 127.1(2) . . . . ? C6 C7 C8 N3 -53.8(3) . . . . ? N3 C8 C9 N4 -0.3(3) . . . . ? C7 C8 C9 N4 178.9(2) . . . . ? N3 C8 C9 C10 -179.9(3) . . . . ? C7 C8 C9 C10 -0.7(5) . . . . ? C11 N4 C9 C8 -0.3(3) . . . . ? C11 N4 C9 C10 179.3(2) . . . . ? C8 N3 C11 N4 -1.1(3) . . . . ? Cu1 N3 C11 N4 176.69(16) . . . . ? C8 N3 C11 C12 179.2(2) . . . . ? Cu1 N3 C11 C12 -3.0(4) . . . . ? C9 N4 C11 N3 0.9(3) . . . . ? C9 N4 C11 C12 -179.4(2) . . . . ? N3 C11 C12 C13 123.2(3) . . . . ? N4 C11 C12 C13 -56.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 35.54 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 2.341 _refine_diff_density_min -1.283 _refine_diff_density_rms 0.133 # Attachment '8925_web_deposit_cif_file_1_Dr.BiplabMondal_1325827290.CIF of complex 3.cif' data_12 _database_code_depnum_ccdc_archive 'CCDC 861294' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H36 Cl Cu N9 O7' _chemical_compound_source Synthesised _exptl_crystal_recrystallization_method Acetonitrile _chemical_melting_point ? _exptl_crystal_description cube _exptl_crystal_colour green _diffrn_ambient_temperature 293(2) _chemical_formula_weight 685.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 19.5792(16) _cell_length_b 9.3484(8) _cell_length_c 18.7219(16) _cell_angle_alpha 90.00 _cell_angle_beta 102.510(5) _cell_angle_gamma 90.00 _cell_volume 3345.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9455 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 19.47 _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.028 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1428 _exptl_absorpt_coefficient_mu 0.787 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36321 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0718 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.07 _diffrn_reflns_theta_max 28.44 _reflns_number_total 8345 _reflns_number_gt 3561 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1639P)^2^+1.0581P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8345 _refine_ls_number_parameters 403 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1588 _refine_ls_R_factor_gt 0.0814 _refine_ls_wR_factor_ref 0.2901 _refine_ls_wR_factor_gt 0.2414 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 2.434 _refine_ls_shift/su_mean 0.028 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 0.30914(4) 0.72882(7) 0.19920(4) 0.0518(3) Uani 1 1 d . . . O1 O 0.3578(3) 0.6427(5) 0.1126(3) 0.0867(14) Uani 1 1 d . . . O3 O 0.4430(6) 0.7069(13) 0.0681(6) 0.208(5) Uani 1 1 d . . . O2 O 0.4027(3) 0.8465(7) 0.1359(4) 0.1064(19) Uani 1 1 d . . . N2 N 0.4768(3) 0.5363(5) 0.3393(3) 0.0611(13) Uani 1 1 d . . . N1 N 0.3934(2) 0.6637(5) 0.2708(2) 0.0500(11) Uani 1 1 d . . . N3 N 0.2839(3) 0.8639(5) 0.2763(3) 0.0621(13) Uani 1 1 d . . . N4 N 0.2313(3) 0.9822(6) 0.3506(3) 0.0748(16) Uani 1 1 d . . . N5 N 0.2419(2) 0.5514(6) 0.2144(3) 0.0614(13) Uani 1 1 d . . . N6 N 0.1665(3) 0.4262(6) 0.2585(4) 0.0820(17) Uani 1 1 d . . . N8 N 0.1652(3) 0.9503(6) 0.0461(3) 0.0683(14) Uani 1 1 d . . . N7 N 0.2371(3) 0.8065(5) 0.1179(3) 0.0584(13) Uani 1 1 d . . . N9 N 0.4011(4) 0.7335(8) 0.1026(4) 0.0837(19) Uani 1 1 d . . . C1 C 0.4165(5) 0.2686(7) 0.2664(5) 0.099(3) Uani 1 1 d . . . H1A H 0.4609 0.2659 0.3002 0.149 Uiso 1 1 calc R . . H1B H 0.4150 0.1952 0.2302 0.149 Uiso 1 1 calc R . . H1C H 0.3798 0.2529 0.2922 0.149 Uiso 1 1 calc R . . C2 C 0.4068(4) 0.4120(6) 0.2296(4) 0.0729(19) Uani 1 1 d . . . H2A H 0.4354 0.4156 0.1933 0.087 Uiso 1 1 calc R . . H2B H 0.3583 0.4209 0.2039 0.087 Uiso 1 1 calc R . . C3 C 0.4248(3) 0.5369(6) 0.2794(3) 0.0554(15) Uani 1 1 d . . . C4 C 0.4801(3) 0.6699(6) 0.3721(3) 0.0575(15) Uani 1 1 d . . . C5 C 0.5330(4) 0.7036(8) 0.4387(4) 0.086(2) Uani 1 1 d . . . H5A H 0.5639 0.7752 0.4272 0.103 Uiso 1 1 d R . . H5B H 0.5595 0.6183 0.4554 0.103 Uiso 1 1 d R . . H5C H 0.5101 0.7367 0.4753 0.103 Uiso 1 1 d R . . C6 C 0.4292(3) 0.7480(5) 0.3283(3) 0.0508(14) Uani 1 1 d . . . C7 C 0.4096(3) 0.9016(6) 0.3334(4) 0.0620(16) Uani 1 1 d . . . H7A H 0.4371 0.9413 0.3784 0.074 Uiso 1 1 calc R . . H7B H 0.4217 0.9535 0.2930 0.074 Uiso 1 1 calc R . . C8 C 0.3342(3) 0.9249(6) 0.3320(3) 0.0574(15) Uani 1 1 d . . . C9 C 0.3028(4) 1.0002(7) 0.3776(4) 0.0733(19) Uani 1 1 d . . . C10 C 0.3318(4) 1.0819(8) 0.4459(4) 0.090(2) Uani 1 1 d . . . H10A H 0.3289 1.0214 0.4878 0.108 Uiso 1 1 d R . . H10B H 0.2993 1.1369 0.4587 0.108 Uiso 1 1 d R . . H10C H 0.3780 1.1099 0.4484 0.108 Uiso 1 1 d R . . C11 C 0.2215(4) 0.8996(8) 0.2896(4) 0.0727(19) Uani 1 1 d . . . C13 C 0.1005(7) 0.919(3) 0.2538(13) 0.45(3) Uani 1 1 d . . . H12A H 0.0991 0.9242 0.3046 0.681 Uiso 1 1 calc R . . H12B H 0.0601 0.8675 0.2278 0.681 Uiso 1 1 calc R . . H12C H 0.1005 1.0134 0.2341 0.681 Uiso 1 1 calc R . . C12 C 0.1512(4) 0.8585(11) 0.2474(5) 0.105(3) Uani 1 1 d . . . H13A H 0.1529 0.8636 0.1961 0.126 Uiso 1 1 calc R . . H13B H 0.1447 0.7585 0.2581 0.126 Uiso 1 1 calc R . . C16 C 0.2283(4) 0.4955(8) 0.2745(4) 0.0753(19) Uani 1 1 d . . . C17 C 0.1383(3) 0.4387(7) 0.1846(4) 0.0674(17) Uani 1 1 d . . . C18 C 0.0707(4) 0.3730(10) 0.1481(5) 0.107(3) Uani 1 1 d . . . H16A H 0.0514 0.4246 0.1040 0.161 Uiso 1 1 calc R . . H16B H 0.0387 0.3770 0.1804 0.161 Uiso 1 1 calc R . . H16C H 0.0782 0.2751 0.1364 0.161 Uiso 1 1 calc R . . C19 C 0.1860(3) 0.5178(6) 0.1585(3) 0.0569(15) Uani 1 1 d . . . C20 C 0.1842(3) 0.5662(6) 0.0815(3) 0.0620(16) Uani 1 1 d . . . H18A H 0.2245 0.5278 0.0657 0.074 Uiso 1 1 calc R . . H18B H 0.1424 0.5288 0.0493 0.074 Uiso 1 1 calc R . . C15 C 0.2744(4) 0.4995(14) 0.3507(5) 0.124(4) Uani 1 1 d . . . H19A H 0.2826 0.4020 0.3681 0.149 Uiso 1 1 calc R . . H19B H 0.3193 0.5397 0.3475 0.149 Uiso 1 1 calc R . . C14 C 0.2479(7) 0.5783(16) 0.4030(6) 0.173(5) Uani 1 1 d . . . H20A H 0.2778 0.6588 0.4188 0.259 Uiso 1 1 calc R . . H20B H 0.2464 0.5182 0.4442 0.259 Uiso 1 1 calc R . . H20C H 0.2016 0.6113 0.3815 0.259 Uiso 1 1 calc R . . C21 C 0.1845(3) 0.7250(6) 0.0756(3) 0.0528(14) Uani 1 1 d . . . C22 C 0.1397(3) 0.8114(7) 0.0302(3) 0.0615(16) Uani 1 1 d . . . C24 C 0.2234(4) 0.9414(7) 0.0980(4) 0.0701(18) Uani 1 1 d . . . C25 C 0.2646(5) 1.0699(7) 0.1291(5) 0.102(3) Uani 1 1 d . . . H24A H 0.2490 1.0960 0.1731 0.123 Uiso 1 1 calc R . . H24B H 0.3129 1.0396 0.1446 0.123 Uiso 1 1 calc R . . C26 C 0.2647(9) 1.1890(12) 0.0903(8) 0.208(8) Uani 1 1 d . . . H25A H 0.2284 1.1837 0.0467 0.312 Uiso 1 1 calc R . . H25B H 0.3092 1.1994 0.0772 0.312 Uiso 1 1 calc R . . H25C H 0.2565 1.2698 0.1190 0.312 Uiso 1 1 calc R . . C23 C 0.0732(4) 0.7831(9) -0.0265(4) 0.090(2) Uani 1 1 d . . . H52A H 0.0814 0.8000 -0.0745 0.135 Uiso 1 1 calc R . . H52B H 0.0369 0.8458 -0.0181 0.135 Uiso 1 1 calc R . . H52C H 0.0591 0.6855 -0.0228 0.135 Uiso 1 1 calc R . . Cl1 Cl 0.09148(12) 0.2317(2) 0.41177(11) 0.0800(6) Uani 1 1 d . . . O5 O 0.0882(5) 0.2971(11) 0.4761(6) 0.200(5) Uani 1 1 d . . . O4 O 0.1533(7) 0.188(2) 0.4135(8) 0.364(12) Uani 1 1 d . . . O7 O 0.0715(8) 0.2947(19) 0.3536(9) 0.342(11) Uani 1 1 d . . . O6 O 0.0639(13) 0.1115(17) 0.4134(7) 0.400(14) 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 0.0459(5) 0.0506(4) 0.0538(5) -0.0043(3) -0.0003(3) -0.0068(3) O1 0.090(4) 0.085(3) 0.082(3) -0.010(3) 0.010(3) -0.018(3) O3 0.165(9) 0.329(14) 0.153(8) -0.023(8) 0.087(8) -0.063(8) O2 0.093(4) 0.088(4) 0.120(5) 0.001(3) -0.017(3) -0.024(3) N2 0.060(3) 0.055(3) 0.066(3) -0.004(2) 0.008(3) 0.001(2) N1 0.046(3) 0.044(2) 0.055(3) -0.004(2) 0.002(2) -0.004(2) N3 0.047(3) 0.077(4) 0.055(3) -0.006(3) -0.005(2) 0.005(2) N4 0.065(4) 0.088(4) 0.066(4) -0.011(3) 0.002(3) 0.015(3) N5 0.048(3) 0.077(3) 0.056(3) 0.004(3) 0.005(3) -0.010(2) N6 0.065(4) 0.089(4) 0.093(5) 0.010(3) 0.020(4) -0.014(3) N8 0.058(3) 0.069(3) 0.067(4) 0.008(3) -0.009(3) -0.009(3) N7 0.057(3) 0.054(3) 0.056(3) -0.003(2) -0.007(2) -0.015(2) N9 0.065(4) 0.103(5) 0.089(5) 0.001(4) 0.029(4) -0.022(4) C1 0.119(7) 0.054(4) 0.111(7) -0.009(4) -0.006(6) -0.010(4) C2 0.068(4) 0.055(4) 0.092(5) -0.022(3) 0.009(4) 0.000(3) C3 0.052(4) 0.044(3) 0.067(4) -0.008(3) 0.005(3) -0.002(2) C4 0.043(4) 0.065(4) 0.058(4) -0.008(3) -0.003(3) 0.002(3) C5 0.077(5) 0.092(5) 0.077(5) -0.020(4) -0.006(4) 0.004(4) C6 0.040(3) 0.049(3) 0.062(4) -0.009(3) 0.006(3) -0.004(2) C7 0.050(4) 0.054(3) 0.071(4) -0.012(3) -0.012(3) -0.003(3) C8 0.049(4) 0.051(3) 0.067(4) -0.003(3) 0.002(3) 0.002(3) C9 0.078(5) 0.060(4) 0.071(4) -0.011(3) -0.006(4) 0.015(3) C10 0.094(6) 0.094(5) 0.072(5) -0.031(4) -0.002(4) 0.019(4) C11 0.063(5) 0.085(5) 0.065(5) -0.005(4) 0.004(4) 0.016(4) C13 0.077(10) 0.77(6) 0.48(4) -0.51(4) -0.008(14) 0.006(18) C12 0.037(5) 0.170(9) 0.105(6) -0.017(6) 0.007(4) 0.019(5) C16 0.065(5) 0.091(5) 0.066(5) 0.023(4) 0.007(4) -0.008(4) C17 0.054(4) 0.069(4) 0.081(5) 0.003(3) 0.017(4) -0.012(3) C18 0.077(6) 0.112(7) 0.131(7) -0.001(5) 0.019(5) -0.041(5) C19 0.061(4) 0.047(3) 0.065(4) -0.006(3) 0.017(3) -0.010(3) C20 0.058(4) 0.061(4) 0.061(4) -0.010(3) -0.001(3) -0.017(3) C15 0.082(6) 0.217(12) 0.072(6) 0.010(7) 0.014(5) -0.041(7) C14 0.211(14) 0.208(14) 0.112(9) -0.013(9) 0.062(9) -0.047(11) C21 0.053(4) 0.061(3) 0.042(3) -0.003(3) 0.007(3) -0.018(3) C22 0.052(4) 0.071(4) 0.053(4) 0.006(3) -0.007(3) -0.014(3) C24 0.069(5) 0.063(4) 0.070(4) 0.009(3) -0.005(4) -0.015(3) C25 0.115(7) 0.053(4) 0.114(7) 0.001(4) -0.031(5) -0.025(4) C26 0.264(18) 0.087(8) 0.207(15) 0.032(9) -0.092(13) -0.048(9) C23 0.064(5) 0.117(6) 0.076(5) 0.017(4) -0.013(4) -0.006(4) Cl1 0.0935(15) 0.0707(11) 0.0788(13) -0.0018(9) 0.0254(11) -0.0020(10) O5 0.148(8) 0.241(10) 0.224(11) -0.139(9) 0.072(8) -0.046(7) O4 0.200(13) 0.60(3) 0.284(17) -0.127(19) 0.037(12) 0.211(17) O7 0.282(16) 0.45(2) 0.293(17) 0.265(18) 0.061(14) 0.039(15) O6 0.68(3) 0.292(16) 0.247(14) -0.085(11) 0.144(17) -0.38(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 N7 1.977(5) . ? Cu1 N1 1.983(5) . ? Cu1 N3 2.057(5) . ? Cu1 N5 2.174(5) . ? Cu1 O1 2.204(5) . ? O1 N9 1.242(7) . ? O3 N9 1.176(10) . ? O2 N9 1.223(8) . ? N2 C3 1.342(7) . ? N2 C4 1.387(7) . ? N1 C3 1.329(7) . ? N1 C6 1.394(7) . ? N3 C11 1.340(8) . ? N3 C8 1.391(7) . ? N4 C11 1.357(8) . ? N4 C9 1.392(8) . ? N5 C16 1.319(8) . ? N5 C19 1.376(7) . ? N6 C16 1.347(8) . ? N6 C17 1.380(8) . ? N8 C24 1.331(8) . ? N8 C22 1.399(8) . ? N7 C24 1.326(8) . ? N7 C21 1.383(7) . ? C1 C2 1.500(10) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.488(8) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C4 C6 1.358(8) . ? C4 C5 1.473(9) . ? C5 H5A 0.9565 . ? C5 H5B 0.9662 . ? C5 H5C 0.9485 . ? C6 C7 1.494(7) . ? C7 C8 1.487(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.353(8) . ? C9 C10 1.492(9) . ? C10 H10A 0.9778 . ? C10 H10B 0.8899 . ? C10 H10C 0.9330 . ? C11 C12 1.482(10) . ? C13 C12 1.169(16) . ? C13 H12A 0.9842 . ? C13 H12B 0.9837 . ? C13 H12C 0.9846 . ? C12 H13A 0.9700 . ? C12 H13B 0.9700 . ? C16 C15 1.514(10) . ? C17 C19 1.362(8) . ? C17 C18 1.485(9) . ? C18 H16A 0.9600 . ? C18 H16B 0.9600 . ? C18 H16C 0.9600 . ? C19 C20 1.504(8) . ? C20 C21 1.489(8) . ? C20 H18A 0.9700 . ? C20 H18B 0.9700 . ? C15 C14 1.411(15) . ? C15 H19A 0.9700 . ? C15 H19B 0.9700 . ? C14 H20A 0.9600 . ? C14 H20B 0.9600 . ? C14 H20C 0.9600 . ? C21 C22 1.349(8) . ? C22 C23 1.516(9) . ? C24 C25 1.492(9) . ? C25 C26 1.330(13) . ? C25 H24A 0.9700 . ? C25 H24B 0.9700 . ? C26 H25A 0.9600 . ? C26 H25B 0.9600 . ? C26 H25C 0.9600 . ? C23 H52A 0.9600 . ? C23 H52B 0.9600 . ? C23 H52C 0.9600 . ? Cl1 O7 1.226(11) . ? Cl1 O6 1.250(9) . ? Cl1 O4 1.272(10) . ? Cl1 O5 1.364(8) . ? 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 N7 Cu1 N1 169.8(2) . . ? N7 Cu1 N3 94.3(2) . . ? N1 Cu1 N3 90.30(18) . . ? N7 Cu1 N5 91.68(19) . . ? N1 Cu1 N5 96.69(18) . . ? N3 Cu1 N5 97.6(2) . . ? N7 Cu1 O1 85.3(2) . . ? N1 Cu1 O1 87.48(19) . . ? N3 Cu1 O1 161.6(2) . . ? N5 Cu1 O1 100.85(19) . . ? N9 O1 Cu1 106.2(5) . . ? C3 N2 C4 108.7(5) . . ? C3 N1 C6 105.6(5) . . ? C3 N1 Cu1 130.6(4) . . ? C6 N1 Cu1 123.6(4) . . ? C11 N3 C8 106.5(5) . . ? C11 N3 Cu1 130.6(4) . . ? C8 N3 Cu1 122.6(4) . . ? C11 N4 C9 108.8(6) . . ? C16 N5 C19 106.5(5) . . ? C16 N5 Cu1 130.8(5) . . ? C19 N5 Cu1 118.6(4) . . ? C16 N6 C17 109.1(6) . . ? C24 N8 C22 107.9(5) . . ? C24 N7 C21 106.5(5) . . ? C24 N7 Cu1 129.2(4) . . ? C21 N7 Cu1 123.9(4) . . ? O3 N9 O2 121.2(9) . . ? O3 N9 O1 121.2(9) . . ? O2 N9 O1 117.2(7) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.4 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C1 115.1(6) . . ? C3 C2 H2A 108.5 . . ? C1 C2 H2A 108.5 . . ? C3 C2 H2B 108.5 . . ? C1 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? N1 C3 N2 110.6(5) . . ? N1 C3 C2 125.7(5) . . ? N2 C3 C2 123.6(5) . . ? C6 C4 N2 105.0(5) . . ? C6 C4 C5 133.3(6) . . ? N2 C4 C5 121.6(6) . . ? C4 C5 H5A 108.8 . . ? C4 C5 H5B 109.1 . . ? H5A C5 H5B 109.2 . . ? C4 C5 H5C 109.0 . . ? H5A C5 H5C 110.8 . . ? H5B C5 H5C 109.8 . . ? C4 C6 N1 110.0(5) . . ? C4 C6 C7 130.0(5) . . ? N1 C6 C7 119.9(5) . . ? C8 C7 C6 114.1(5) . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7A 108.7 . . ? C8 C7 H7B 108.7 . . ? C6 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C9 C8 N3 110.0(5) . . ? C9 C8 C7 130.5(6) . . ? N3 C8 C7 119.5(5) . . ? C8 C9 N4 105.4(6) . . ? C8 C9 C10 131.8(7) . . ? N4 C9 C10 122.7(6) . . ? C9 C10 H10A 108.3 . . ? C9 C10 H10B 111.3 . . ? H10A C10 H10B 87.1 . . ? C9 C10 H10C 111.8 . . ? H10A C10 H10C 110.3 . . ? H10B C10 H10C 124.4 . . ? N3 C11 N4 109.3(6) . . ? N3 C11 C12 128.0(6) . . ? N4 C11 C12 122.7(7) . . ? C12 C13 H12A 112.8 . . ? C12 C13 H12B 112.5 . . ? H12A C13 H12B 106.1 . . ? C12 C13 H12C 112.9 . . ? H12A C13 H12C 106.0 . . ? H12B C13 H12C 105.9 . . ? C13 C12 C11 122.2(11) . . ? C13 C12 H13A 107.0 . . ? C11 C12 H13A 106.8 . . ? C13 C12 H13B 106.6 . . ? C11 C12 H13B 106.7 . . ? H13A C12 H13B 106.6 . . ? N5 C16 N6 109.8(6) . . ? N5 C16 C15 127.2(6) . . ? N6 C16 C15 123.0(6) . . ? C19 C17 N6 104.4(6) . . ? C19 C17 C18 132.2(7) . . ? N6 C17 C18 123.3(6) . . ? C17 C18 H16A 109.5 . . ? C17 C18 H16B 109.5 . . ? H16A C18 H16B 109.5 . . ? C17 C18 H16C 109.5 . . ? H16A C18 H16C 109.5 . . ? H16B C18 H16C 109.5 . . ? C17 C19 N5 110.2(6) . . ? C17 C19 C20 129.1(6) . . ? N5 C19 C20 120.7(5) . . ? C21 C20 C19 111.9(5) . . ? C21 C20 H18A 109.2 . . ? C19 C20 H18A 109.2 . . ? C21 C20 H18B 109.2 . . ? C19 C20 H18B 109.2 . . ? H18A C20 H18B 107.9 . . ? C14 C15 C16 115.6(10) . . ? C14 C15 H19A 108.4 . . ? C16 C15 H19A 108.3 . . ? C14 C15 H19B 108.4 . . ? C16 C15 H19B 108.4 . . ? H19A C15 H19B 107.4 . . ? C15 C14 H20A 109.5 . . ? C15 C14 H20B 109.5 . . ? H20A C14 H20B 109.5 . . ? C15 C14 H20C 109.5 . . ? H20A C14 H20C 109.5 . . ? H20B C14 H20C 109.5 . . ? C22 C21 N7 109.4(5) . . ? C22 C21 C20 129.2(5) . . ? N7 C21 C20 121.4(5) . . ? C21 C22 N8 105.6(5) . . ? C21 C22 C23 132.8(6) . . ? N8 C22 C23 121.6(6) . . ? N7 C24 N8 110.6(5) . . ? N7 C24 C25 126.7(6) . . ? N8 C24 C25 122.7(6) . . ? C26 C25 C24 121.7(8) . . ? C26 C25 H24A 106.9 . . ? C24 C25 H24A 106.9 . . ? C26 C25 H24B 106.9 . . ? C24 C25 H24B 106.9 . . ? H24A C25 H24B 106.7 . . ? C25 C26 H25A 109.4 . . ? C25 C26 H25B 109.5 . . ? H25A C26 H25B 109.5 . . ? C25 C26 H25C 109.5 . . ? H25A C26 H25C 109.5 . . ? H25B C26 H25C 109.5 . . ? C22 C23 H52A 109.5 . . ? C22 C23 H52B 109.5 . . ? H52A C23 H52B 109.5 . . ? C22 C23 H52C 109.5 . . ? H52A C23 H52C 109.5 . . ? H52B C23 H52C 109.5 . . ? O7 Cl1 O6 113.4(12) . . ? O7 Cl1 O4 107.3(12) . . ? O6 Cl1 O4 97.0(13) . . ? O7 Cl1 O5 120.1(11) . . ? O6 Cl1 O5 106.2(8) . . ? O4 Cl1 O5 110.5(8) . . ? 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 N7 Cu1 O1 N9 93.1(5) . . . . ? N1 Cu1 O1 N9 -79.7(5) . . . . ? N3 Cu1 O1 N9 3.7(9) . . . . ? N5 Cu1 O1 N9 -176.1(4) . . . . ? N7 Cu1 N1 C3 -96.2(11) . . . . ? N3 Cu1 N1 C3 146.7(5) . . . . ? N5 Cu1 N1 C3 49.0(5) . . . . ? O1 Cu1 N1 C3 -51.7(5) . . . . ? N7 Cu1 N1 C6 89.0(11) . . . . ? N3 Cu1 N1 C6 -28.1(4) . . . . ? N5 Cu1 N1 C6 -125.7(4) . . . . ? O1 Cu1 N1 C6 133.6(4) . . . . ? N7 Cu1 N3 C11 46.2(6) . . . . ? N1 Cu1 N3 C11 -142.9(6) . . . . ? N5 Cu1 N3 C11 -46.1(6) . . . . ? O1 Cu1 N3 C11 134.2(7) . . . . ? N7 Cu1 N3 C8 -141.5(5) . . . . ? N1 Cu1 N3 C8 29.5(5) . . . . ? N5 Cu1 N3 C8 126.3(5) . . . . ? O1 Cu1 N3 C8 -53.4(8) . . . . ? N7 Cu1 N5 C16 -135.7(6) . . . . ? N1 Cu1 N5 C16 50.1(6) . . . . ? N3 Cu1 N5 C16 -41.1(6) . . . . ? O1 Cu1 N5 C16 138.8(6) . . . . ? N7 Cu1 N5 C19 18.3(5) . . . . ? N1 Cu1 N5 C19 -155.9(4) . . . . ? N3 Cu1 N5 C19 112.9(4) . . . . ? O1 Cu1 N5 C19 -67.2(5) . . . . ? N1 Cu1 N7 C24 -67.1(13) . . . . ? N3 Cu1 N7 C24 49.7(6) . . . . ? N5 Cu1 N7 C24 147.5(6) . . . . ? O1 Cu1 N7 C24 -111.8(6) . . . . ? N1 Cu1 N7 C21 121.4(10) . . . . ? N3 Cu1 N7 C21 -121.8(5) . . . . ? N5 Cu1 N7 C21 -24.0(5) . . . . ? O1 Cu1 N7 C21 76.7(5) . . . . ? Cu1 O1 N9 O3 167.5(9) . . . . ? Cu1 O1 N9 O2 -5.6(8) . . . . ? C6 N1 C3 N2 1.2(6) . . . . ? Cu1 N1 C3 N2 -174.3(4) . . . . ? C6 N1 C3 C2 -177.6(6) . . . . ? Cu1 N1 C3 C2 6.9(9) . . . . ? C4 N2 C3 N1 0.0(7) . . . . ? C4 N2 C3 C2 178.9(6) . . . . ? C1 C2 C3 N1 -146.7(7) . . . . ? C1 C2 C3 N2 34.6(10) . . . . ? C3 N2 C4 C6 -1.3(6) . . . . ? C3 N2 C4 C5 -178.9(6) . . . . ? N2 C4 C6 N1 2.0(7) . . . . ? C5 C4 C6 N1 179.2(7) . . . . ? N2 C4 C6 C7 -176.9(6) . . . . ? C5 C4 C6 C7 0.3(12) . . . . ? C3 N1 C6 C4 -2.0(7) . . . . ? Cu1 N1 C6 C4 173.8(4) . . . . ? C3 N1 C6 C7 177.0(6) . . . . ? Cu1 N1 C6 C7 -7.1(7) . . . . ? C4 C6 C7 C8 -127.2(7) . . . . ? N1 C6 C7 C8 54.0(8) . . . . ? C11 N3 C8 C9 -1.6(7) . . . . ? Cu1 N3 C8 C9 -175.6(4) . . . . ? C11 N3 C8 C7 178.7(6) . . . . ? Cu1 N3 C8 C7 4.7(8) . . . . ? C6 C7 C8 C9 128.6(7) . . . . ? C6 C7 C8 N3 -51.7(8) . . . . ? N3 C8 C9 N4 1.5(7) . . . . ? C7 C8 C9 N4 -178.8(6) . . . . ? N3 C8 C9 C10 178.2(7) . . . . ? C7 C8 C9 C10 -2.2(13) . . . . ? C11 N4 C9 C8 -0.9(8) . . . . ? C11 N4 C9 C10 -177.9(7) . . . . ? C8 N3 C11 N4 1.0(7) . . . . ? Cu1 N3 C11 N4 174.3(4) . . . . ? C8 N3 C11 C12 -178.5(8) . . . . ? Cu1 N3 C11 C12 -5.2(11) . . . . ? C9 N4 C11 N3 -0.1(8) . . . . ? C9 N4 C11 C12 179.5(7) . . . . ? N3 C11 C12 C13 -163(2) . . . . ? N4 C11 C12 C13 17(3) . . . . ? C19 N5 C16 N6 0.9(8) . . . . ? Cu1 N5 C16 N6 157.2(5) . . . . ? C19 N5 C16 C15 178.4(9) . . . . ? Cu1 N5 C16 C15 -25.3(12) . . . . ? C17 N6 C16 N5 -0.5(8) . . . . ? C17 N6 C16 C15 -178.2(8) . . . . ? C16 N6 C17 C19 0.0(8) . . . . ? C16 N6 C17 C18 179.2(7) . . . . ? N6 C17 C19 N5 0.6(7) . . . . ? C18 C17 C19 N5 -178.5(8) . . . . ? N6 C17 C19 C20 179.9(6) . . . . ? C18 C17 C19 C20 0.8(12) . . . . ? C16 N5 C19 C17 -0.9(7) . . . . ? Cu1 N5 C19 C17 -160.7(4) . . . . ? C16 N5 C19 C20 179.7(6) . . . . ? Cu1 N5 C19 C20 19.9(7) . . . . ? C17 C19 C20 C21 118.9(7) . . . . ? N5 C19 C20 C21 -61.9(8) . . . . ? N5 C16 C15 C14 114.4(10) . . . . ? N6 C16 C15 C14 -68.4(13) . . . . ? C24 N7 C21 C22 0.3(7) . . . . ? Cu1 N7 C21 C22 173.5(4) . . . . ? C24 N7 C21 C20 178.0(6) . . . . ? Cu1 N7 C21 C20 -8.8(8) . . . . ? C19 C20 C21 C22 -126.3(7) . . . . ? C19 C20 C21 N7 56.5(8) . . . . ? N7 C21 C22 N8 -0.9(7) . . . . ? C20 C21 C22 N8 -178.4(7) . . . . ? N7 C21 C22 C23 -178.9(7) . . . . ? C20 C21 C22 C23 3.6(12) . . . . ? C24 N8 C22 C21 1.1(7) . . . . ? C24 N8 C22 C23 179.4(6) . . . . ? C21 N7 C24 N8 0.4(8) . . . . ? Cu1 N7 C24 N8 -172.2(4) . . . . ? C21 N7 C24 C25 178.8(8) . . . . ? Cu1 N7 C24 C25 6.1(11) . . . . ? C22 N8 C24 N7 -1.0(8) . . . . ? C22 N8 C24 C25 -179.4(7) . . . . ? N7 C24 C25 C26 153.8(13) . . . . ? N8 C24 C25 C26 -28.0(17) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.44 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.913 _refine_diff_density_min -0.502 _refine_diff_density_rms 0.094