data_global_1 _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year 2007 _journal_volume 31 _journal_page_first 669 loop_ _publ_author_name L.Dobrzanska G.O.Lloyd C.Esterhuysen L.J.Barbour data_c:\docume~1\gol\desktop\cubox\cu_~1\xm _database_code_depnum_ccdc_archive 'CCDC 602877' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H24 Cl2 Cu N4 O' _chemical_formula_weight 458.86 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' 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' 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.7300(13) _cell_length_b 13.374(2) _cell_length_c 17.707(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.956(3) _cell_angle_gamma 90.00 _cell_volume 2056.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour 'light brown' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 948 _exptl_absorpt_coefficient_mu 1.338 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7395 _exptl_absorpt_correction_T_max 0.8348 _exptl_absorpt_process_details 'SADABS, Blessing, Acta Cryst. A51 (1995) 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12457 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0577 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4747 _reflns_number_gt 3660 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; X-Seed (Atwood and Barbour, 2003; Barbour, 2001) ; _computing_publication_material ; X-Seed ; _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^)+(0.0643P)^2^+2.6692P] 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 4747 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1284 _refine_ls_wR_factor_gt 0.1197 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.19819(5) 0.19393(3) 0.39982(2) 0.01281(13) Uani 1 1 d . . . Cl1 Cl 0.31714(9) 0.12427(6) 0.30390(5) 0.01592(19) Uani 1 1 d . . . Cl2 Cl -0.01678(9) 0.14849(7) 0.45164(5) 0.0195(2) Uani 1 1 d . . . N1 N 0.1100(3) 0.3126(2) 0.34514(16) 0.0145(6) Uani 1 1 d . . . N4 N 0.6602(3) 0.8580(2) 0.51579(16) 0.0139(6) Uani 1 1 d . . . N3 N 0.4489(3) 0.8898(2) 0.44092(16) 0.0135(6) Uani 1 1 d . . . C6 C 0.1566(4) 0.6256(2) 0.27419(19) 0.0146(7) Uani 1 1 d . . . N2 N 0.0768(3) 0.4474(2) 0.27420(16) 0.0147(6) Uani 1 1 d . . . C2 C -0.0428(4) 0.3426(3) 0.3430(2) 0.0182(7) Uani 1 1 d . . . H2 H -0.1199 0.3102 0.3681 0.022 Uiso 1 1 calc R . . C9 C 0.2472(4) 0.7935(2) 0.36231(19) 0.0134(7) Uani 1 1 d . . . C4 C 0.3442(4) 0.3807(3) 0.2905(2) 0.0225(8) Uani 1 1 d . . . H4A H 0.3938 0.3183 0.3088 0.034 Uiso 1 1 calc R . . H4B H 0.3946 0.4373 0.3181 0.034 Uiso 1 1 calc R . . H4C H 0.3535 0.3881 0.2361 0.034 Uiso 1 1 calc R . . C8 C 0.0949(4) 0.7610(3) 0.35510(19) 0.0158(7) Uani 1 1 d . . . H8 H 0.0209 0.7958 0.3808 0.019 Uiso 1 1 calc R . . C11 C 0.3090(4) 0.6576(3) 0.2811(2) 0.0180(7) Uani 1 1 d . . . H11 H 0.3831 0.6224 0.2557 0.022 Uiso 1 1 calc R . . C1 C 0.1792(4) 0.3783(3) 0.30333(19) 0.0144(7) Uani 1 1 d . . . C3 C -0.0642(4) 0.4253(3) 0.2994(2) 0.0176(7) Uani 1 1 d . . . H3 H -0.1577 0.4613 0.2882 0.021 Uiso 1 1 calc R . . C12 C 0.2886(4) 0.8875(3) 0.40754(19) 0.0144(7) Uani 1 1 d . . . H12A H 0.2692 0.9463 0.3739 0.017 Uiso 1 1 calc R . . H12B H 0.2204 0.8932 0.4487 0.017 Uiso 1 1 calc R . . C13 C 0.5102(4) 0.8386(3) 0.5025(2) 0.0143(7) Uani 1 1 d . . . C5 C 0.1074(4) 0.5341(3) 0.2271(2) 0.0169(7) Uani 1 1 d . . . H5A H 0.0132 0.5502 0.1933 0.020 Uiso 1 1 calc R . . H5B H 0.1895 0.5167 0.1948 0.020 Uiso 1 1 calc R . . C10 C 0.3535(4) 0.7413(3) 0.3251(2) 0.0176(7) Uani 1 1 d . . . H10 H 0.4579 0.7626 0.3296 0.021 Uiso 1 1 calc R . . C16 C 0.4207(4) 0.7710(3) 0.5479(2) 0.0223(8) Uani 1 1 d . . . H16A H 0.4629 0.7032 0.5469 0.033 Uiso 1 1 calc R . . H16B H 0.3127 0.7704 0.5264 0.033 Uiso 1 1 calc R . . H16C H 0.4275 0.7948 0.6005 0.033 Uiso 1 1 calc R . . C15 C 0.6955(4) 0.9249(3) 0.46021(19) 0.0147(7) Uani 1 1 d . . . H15 H 0.7945 0.9521 0.4552 0.018 Uiso 1 1 calc R . . C14 C 0.5646(4) 0.9451(2) 0.41400(19) 0.0142(7) Uani 1 1 d . . . H14 H 0.5550 0.9887 0.3715 0.017 Uiso 1 1 calc R . . C7 C 0.0498(4) 0.6788(3) 0.3111(2) 0.0171(7) Uani 1 1 d . . . H7 H -0.0550 0.6584 0.3061 0.021 Uiso 1 1 calc R . . C19 C 0.2096(7) 0.5348(4) 0.4748(3) 0.0493(14) Uani 1 1 d . . . H19A H 0.1567 0.5940 0.4918 0.074 Uiso 1 1 calc R . . H19B H 0.1333 0.4872 0.4516 0.074 Uiso 1 1 calc R . . H19C H 0.2791 0.5546 0.4374 0.074 Uiso 1 1 calc R . . C18 C 0.2645(6) 0.3867(4) 0.5646(3) 0.0496(13) Uani 1 1 d . . . H18A H 0.3181 0.3728 0.6149 0.074 Uiso 1 1 calc R . . H18B H 0.2974 0.3386 0.5278 0.074 Uiso 1 1 calc R . . H18C H 0.1531 0.3810 0.5667 0.074 Uiso 1 1 calc R . . C17 C 0.3011(7) 0.4864(4) 0.5417(4) 0.0615(17) Uani 1 1 d . . . O1 O 0.3981(12) 0.5302(5) 0.5789(5) 0.260(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0120(2) 0.0135(2) 0.0129(2) 0.00227(16) 0.00098(15) 0.00064(16) Cl1 0.0150(4) 0.0176(4) 0.0154(4) 0.0015(3) 0.0022(3) 0.0022(3) Cl2 0.0142(4) 0.0254(5) 0.0194(4) 0.0053(4) 0.0036(3) -0.0014(3) N1 0.0149(14) 0.0131(14) 0.0153(14) -0.0009(11) 0.0012(11) 0.0005(11) N4 0.0142(14) 0.0139(15) 0.0130(14) 0.0011(11) -0.0012(11) -0.0003(11) N3 0.0147(14) 0.0124(14) 0.0131(14) 0.0003(11) -0.0011(11) -0.0004(11) C6 0.0198(18) 0.0122(16) 0.0113(16) 0.0034(13) -0.0001(13) 0.0001(13) N2 0.0177(15) 0.0108(14) 0.0147(15) -0.0003(11) -0.0021(12) 0.0015(11) C2 0.0157(17) 0.0167(18) 0.0224(19) -0.0021(15) 0.0028(14) 0.0007(14) C9 0.0139(16) 0.0134(17) 0.0123(16) 0.0043(13) -0.0021(13) -0.0007(13) C4 0.0153(18) 0.023(2) 0.030(2) 0.0101(16) 0.0068(16) -0.0004(14) C8 0.0137(16) 0.0188(18) 0.0148(17) 0.0019(14) 0.0009(13) 0.0028(13) C11 0.0158(17) 0.0164(17) 0.0225(19) 0.0015(14) 0.0051(15) 0.0034(14) C1 0.0172(17) 0.0131(16) 0.0126(16) -0.0012(13) -0.0003(13) -0.0003(13) C3 0.0152(17) 0.0168(18) 0.0201(19) -0.0015(14) -0.0012(14) 0.0030(14) C12 0.0139(17) 0.0152(17) 0.0135(17) 0.0009(13) -0.0015(13) 0.0002(13) C13 0.0120(16) 0.0131(16) 0.0175(17) 0.0002(13) 0.0008(13) -0.0012(13) C5 0.0217(18) 0.0139(17) 0.0137(17) 0.0021(13) -0.0039(14) 0.0027(14) C10 0.0153(17) 0.0173(18) 0.0200(18) 0.0039(14) 0.0015(14) -0.0020(14) C16 0.0168(18) 0.026(2) 0.023(2) 0.0117(16) -0.0019(15) -0.0043(15) C15 0.0154(17) 0.0134(16) 0.0157(17) -0.0015(13) 0.0029(13) -0.0030(13) C14 0.0198(17) 0.0127(16) 0.0101(16) 0.0010(13) 0.0011(13) -0.0013(13) C7 0.0149(17) 0.0177(18) 0.0175(18) 0.0011(14) -0.0045(14) 0.0009(13) C19 0.068(4) 0.036(3) 0.040(3) 0.002(2) -0.016(3) -0.013(3) C18 0.050(3) 0.040(3) 0.058(3) 0.010(3) 0.002(3) -0.002(2) C17 0.076(4) 0.031(3) 0.070(4) 0.009(3) -0.031(3) -0.014(3) O1 0.343(11) 0.090(5) 0.281(9) 0.116(6) -0.275(9) -0.132(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 Cu1 N4 1.965(3) 3_666 ? Cu1 N1 1.974(3) . ? Cu1 Cl2 2.2562(9) . ? Cu1 Cl1 2.2797(9) . ? N1 C1 1.333(4) . ? N1 C2 1.389(4) . ? N4 C13 1.332(4) . ? N4 C15 1.388(4) . ? N4 Cu1 1.965(3) 3_666 ? N3 C13 1.350(4) . ? N3 C14 1.376(4) . ? N3 C12 1.462(4) . ? C6 C7 1.389(5) . ? C6 C11 1.391(5) . ? C6 C5 1.517(5) . ? N2 C1 1.350(4) . ? N2 C3 1.384(4) . ? N2 C5 1.469(4) . ? C2 C3 1.350(5) . ? C9 C10 1.382(5) . ? C9 C8 1.392(5) . ? C9 C12 1.515(5) . ? C4 C1 1.482(5) . ? C8 C7 1.380(5) . ? C11 C10 1.396(5) . ? C13 C16 1.485(5) . ? C15 C14 1.362(5) . ? C19 C17 1.504(7) . ? C18 C17 1.439(7) . ? C17 O1 1.173(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 N4 Cu1 N1 147.16(12) 3_666 . ? N4 Cu1 Cl2 94.57(9) 3_666 . ? N1 Cu1 Cl2 96.74(9) . . ? N4 Cu1 Cl1 97.05(9) 3_666 . ? N1 Cu1 Cl1 98.51(9) . . ? Cl2 Cu1 Cl1 130.94(4) . . ? C1 N1 C2 106.4(3) . . ? C1 N1 Cu1 128.8(2) . . ? C2 N1 Cu1 124.8(2) . . ? C13 N4 C15 106.7(3) . . ? C13 N4 Cu1 126.5(2) . 3_666 ? C15 N4 Cu1 126.8(2) . 3_666 ? C13 N3 C14 108.0(3) . . ? C13 N3 C12 126.8(3) . . ? C14 N3 C12 125.3(3) . . ? C7 C6 C11 118.9(3) . . ? C7 C6 C5 120.4(3) . . ? C11 C6 C5 120.7(3) . . ? C1 N2 C3 107.9(3) . . ? C1 N2 C5 127.2(3) . . ? C3 N2 C5 124.9(3) . . ? C3 C2 N1 109.2(3) . . ? C10 C9 C8 118.7(3) . . ? C10 C9 C12 122.4(3) . . ? C8 C9 C12 118.8(3) . . ? C7 C8 C9 120.9(3) . . ? C6 C11 C10 120.3(3) . . ? N1 C1 N2 110.0(3) . . ? N1 C1 C4 127.1(3) . . ? N2 C1 C4 122.8(3) . . ? C2 C3 N2 106.5(3) . . ? N3 C12 C9 113.4(3) . . ? N4 C13 N3 110.1(3) . . ? N4 C13 C16 125.8(3) . . ? N3 C13 C16 124.0(3) . . ? N2 C5 C6 112.5(3) . . ? C9 C10 C11 120.6(3) . . ? C14 C15 N4 108.6(3) . . ? C15 C14 N3 106.6(3) . . ? C8 C7 C6 120.5(3) . . ? O1 C17 C18 118.2(6) . . ? O1 C17 C19 121.4(5) . . ? C18 C17 C19 120.3(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 N4 Cu1 N1 C1 68.3(4) 3_666 . . . ? Cl2 Cu1 N1 C1 177.7(3) . . . . ? Cl1 Cu1 N1 C1 -49.1(3) . . . . ? N4 Cu1 N1 C2 -112.5(3) 3_666 . . . ? Cl2 Cu1 N1 C2 -3.1(3) . . . . ? Cl1 Cu1 N1 C2 130.1(3) . . . . ? C1 N1 C2 C3 0.6(4) . . . . ? Cu1 N1 C2 C3 -178.8(2) . . . . ? C10 C9 C8 C7 -0.6(5) . . . . ? C12 C9 C8 C7 176.5(3) . . . . ? C7 C6 C11 C10 0.6(5) . . . . ? C5 C6 C11 C10 -179.4(3) . . . . ? C2 N1 C1 N2 -0.8(4) . . . . ? Cu1 N1 C1 N2 178.5(2) . . . . ? C2 N1 C1 C4 177.5(3) . . . . ? Cu1 N1 C1 C4 -3.1(5) . . . . ? C3 N2 C1 N1 0.7(4) . . . . ? C5 N2 C1 N1 178.0(3) . . . . ? C3 N2 C1 C4 -177.7(3) . . . . ? C5 N2 C1 C4 -0.5(5) . . . . ? N1 C2 C3 N2 -0.1(4) . . . . ? C1 N2 C3 C2 -0.3(4) . . . . ? C5 N2 C3 C2 -177.7(3) . . . . ? C13 N3 C12 C9 -75.9(4) . . . . ? C14 N3 C12 C9 103.7(4) . . . . ? C10 C9 C12 N3 -29.9(4) . . . . ? C8 C9 C12 N3 153.1(3) . . . . ? C15 N4 C13 N3 0.2(4) . . . . ? Cu1 N4 C13 N3 178.0(2) 3_666 . . . ? C15 N4 C13 C16 -179.7(3) . . . . ? Cu1 N4 C13 C16 -1.9(5) 3_666 . . . ? C14 N3 C13 N4 -0.5(4) . . . . ? C12 N3 C13 N4 179.2(3) . . . . ? C14 N3 C13 C16 179.4(3) . . . . ? C12 N3 C13 C16 -1.0(6) . . . . ? C1 N2 C5 C6 -87.8(4) . . . . ? C3 N2 C5 C6 89.0(4) . . . . ? C7 C6 C5 N2 -73.4(4) . . . . ? C11 C6 C5 N2 106.6(4) . . . . ? C8 C9 C10 C11 0.1(5) . . . . ? C12 C9 C10 C11 -177.0(3) . . . . ? C6 C11 C10 C9 -0.1(5) . . . . ? C13 N4 C15 C14 0.2(4) . . . . ? Cu1 N4 C15 C14 -177.6(2) 3_666 . . . ? N4 C15 C14 N3 -0.5(4) . . . . ? C13 N3 C14 C15 0.6(4) . . . . ? C12 N3 C14 C15 -179.1(3) . . . . ? C9 C8 C7 C6 1.2(5) . . . . ? C11 C6 C7 C8 -1.2(5) . . . . ? C5 C6 C7 C8 178.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 1.716 _refine_diff_density_min -1.601 _refine_diff_density_rms 0.112 # Attachment '3.CIF' data_c:\docume~1\gol\desktop\cubox\acetr2~1\xm _database_code_depnum_ccdc_archive 'CCDC 602879' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 3 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H21 Cl2 Cu N5' _chemical_formula_weight 441.84 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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.590(2) _cell_length_b 12.854(3) _cell_length_c 18.163(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.596(4) _cell_angle_gamma 90.00 _cell_volume 2004.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 908 _exptl_absorpt_coefficient_mu 1.368 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7349 _exptl_absorpt_correction_T_max 0.8316 _exptl_absorpt_process_details 'SADABS, Blessing, Acta Cryst. A51 (1995) 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8012 _diffrn_reflns_av_R_equivalents 0.1185 _diffrn_reflns_av_sigmaI/netI 0.1961 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 28.01 _reflns_number_total 4213 _reflns_number_gt 2245 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; X-Seed (Atwood and Barbour, 2003; Barbour, 2001) ; _computing_publication_material ; X-Seed ; _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^)+(0.0614P)^2^+24.2096P] 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 4213 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1973 _refine_ls_R_factor_gt 0.1044 _refine_ls_wR_factor_ref 0.2310 _refine_ls_wR_factor_gt 0.1959 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.736 _refine_ls_shift/su_mean 0.005 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 0.25227(14) 0.18982(9) 0.38183(7) 0.0103(3) Uani 1 1 d . . . Cl1 Cl 0.0198(3) 0.11544(18) 0.40853(13) 0.0121(5) Uani 1 1 d . . . Cl2 Cl 0.4234(3) 0.1266(2) 0.29958(14) 0.0179(6) Uani 1 1 d . . . N4 N 0.8264(9) 0.6964(7) 0.6807(4) 0.0135(18) Uani 1 1 d . . . N3 N 0.9503(9) 0.5557(6) 0.7169(4) 0.0109(18) Uani 1 1 d . . . C2 C 0.3014(12) 0.0991(7) 0.5332(5) 0.012(2) Uani 1 1 d . . . H2 H 0.1951 0.0799 0.5370 0.014 Uiso 1 1 calc R . . N1 N 0.3628(10) 0.1544(6) 0.4747(4) 0.0128(19) Uani 1 1 d . . . C1 C 0.5129(11) 0.1678(8) 0.4910(6) 0.015(2) Uani 1 1 d . . . C15 C 0.7957(12) 0.6753(7) 0.7542(5) 0.013(2) Uani 1 1 d . . . H15 H 0.7296 0.7152 0.7844 0.016 Uiso 1 1 calc R . . N2 N 0.5505(9) 0.1218(6) 0.5570(4) 0.0113(18) Uani 1 1 d . . . C13 C 0.9214(11) 0.6200(8) 0.6595(5) 0.013(2) Uani 1 1 d . . . C5 C 0.7092(11) 0.1037(8) 0.5890(6) 0.015(2) Uani 1 1 d . . . H5A H 0.7756 0.0749 0.5503 0.018 Uiso 1 1 calc R . . H5B H 0.7027 0.0508 0.6284 0.018 Uiso 1 1 calc R . . C7 C 0.7469(12) 0.2408(8) 0.6885(6) 0.017(2) Uani 1 1 d . . . H7 H 0.6643 0.2104 0.7148 0.020 Uiso 1 1 calc R . . C3 C 0.4156(11) 0.0767(8) 0.5841(5) 0.013(2) Uani 1 1 d . . . H3 H 0.4058 0.0386 0.6285 0.016 Uiso 1 1 calc R . . C12 C 1.0445(12) 0.4594(7) 0.7153(5) 0.011(2) Uani 1 1 d . . . H12A H 1.0781 0.4408 0.7662 0.013 Uiso 1 1 calc R . . H12B H 1.1392 0.4722 0.6867 0.013 Uiso 1 1 calc R . . C10 C 0.9951(11) 0.3270(7) 0.6152(5) 0.013(2) Uani 1 1 d . . . H10 H 1.0792 0.3565 0.5895 0.015 Uiso 1 1 calc R . . C6 C 0.7873(11) 0.2002(8) 0.6209(5) 0.013(2) Uani 1 1 d . . . C14 C 0.8724(12) 0.5914(8) 0.7752(5) 0.013(2) Uani 1 1 d . . . H14 H 0.8730 0.5613 0.8230 0.015 Uiso 1 1 calc R . . C9 C 0.9544(12) 0.3687(8) 0.6809(6) 0.015(2) Uani 1 1 d . . . C8 C 0.8274(12) 0.3259(8) 0.7179(6) 0.015(2) Uani 1 1 d . . . H8 H 0.7965 0.3554 0.7632 0.018 Uiso 1 1 calc R . . C4 C 0.6270(13) 0.2264(10) 0.4478(6) 0.028(3) Uani 1 1 d . . . H4A H 0.7120 0.1799 0.4343 0.042 Uiso 1 1 calc R . . H4B H 0.6690 0.2841 0.4775 0.042 Uiso 1 1 calc R . . H4C H 0.5755 0.2538 0.4031 0.042 Uiso 1 1 calc R . . C11 C 0.9165(12) 0.2432(8) 0.5853(5) 0.014(2) Uani 1 1 d . . . H11 H 0.9496 0.2138 0.5404 0.016 Uiso 1 1 calc R . . C16 C 0.9850(14) 0.6075(8) 0.5844(6) 0.024(3) Uani 1 1 d . . . H16A H 0.9673 0.6716 0.5562 0.037 Uiso 1 1 calc R . . H16B H 0.9324 0.5494 0.5592 0.037 Uiso 1 1 calc R . . H16C H 1.0970 0.5934 0.5885 0.037 Uiso 1 1 calc R . . C18 C 0.5689(15) 0.5347(11) 0.4183(7) 0.034(3) Uani 1 1 d . . . C17 C 0.4401(18) 0.5055(15) 0.3721(9) 0.070(6) Uani 1 1 d . . . H17A H 0.4418 0.4301 0.3642 0.105 Uiso 1 1 calc R . . H17B H 0.4466 0.5412 0.3246 0.105 Uiso 1 1 calc R . . H17C H 0.3431 0.5250 0.3956 0.105 Uiso 1 1 calc R . . N5 N 0.6739(15) 0.5513(16) 0.4554(7) 0.086(6) 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 0.0117(6) 0.0088(6) 0.0103(6) 0.0028(5) -0.0010(5) -0.0013(5) Cl1 0.0137(13) 0.0098(11) 0.0129(12) -0.0003(9) 0.0015(10) -0.0025(9) Cl2 0.0184(14) 0.0166(13) 0.0188(14) 0.0060(10) 0.0050(11) 0.0060(11) N4 0.015(5) 0.017(4) 0.008(4) 0.007(4) -0.002(3) 0.001(4) N3 0.014(5) 0.007(4) 0.011(4) 0.003(3) -0.003(4) 0.002(3) C2 0.016(6) 0.007(5) 0.012(5) 0.004(4) 0.001(4) 0.003(4) N1 0.015(5) 0.012(4) 0.011(4) -0.001(3) 0.000(4) 0.004(3) C1 0.006(5) 0.022(6) 0.017(6) 0.005(4) -0.003(4) 0.000(4) C15 0.028(6) 0.012(5) 0.000(4) -0.004(4) 0.003(4) -0.002(4) N2 0.013(5) 0.009(4) 0.013(4) 0.002(3) -0.002(4) -0.005(3) C13 0.008(5) 0.010(5) 0.019(6) 0.000(4) -0.009(4) -0.005(4) C5 0.011(5) 0.010(5) 0.023(6) 0.003(4) -0.008(4) -0.001(4) C7 0.011(6) 0.016(5) 0.023(6) 0.003(4) 0.002(5) 0.003(4) C3 0.013(6) 0.018(5) 0.008(5) 0.000(4) 0.005(4) -0.002(4) C12 0.016(6) 0.015(5) 0.001(5) -0.001(4) 0.004(4) -0.002(4) C10 0.012(5) 0.006(5) 0.019(5) 0.002(4) 0.000(4) 0.001(4) C6 0.017(6) 0.009(5) 0.012(5) -0.003(4) -0.004(4) 0.003(4) C14 0.021(6) 0.017(5) 0.000(5) 0.002(4) 0.005(4) -0.001(4) C9 0.015(6) 0.012(5) 0.016(6) 0.005(4) -0.004(4) -0.002(4) C8 0.019(6) 0.012(5) 0.015(5) -0.001(4) 0.004(4) -0.001(4) C4 0.017(6) 0.038(7) 0.028(7) 0.005(5) -0.004(5) -0.010(5) C11 0.015(6) 0.015(5) 0.011(5) -0.001(4) 0.001(4) 0.000(4) C16 0.036(7) 0.011(5) 0.026(6) 0.009(5) 0.002(5) 0.015(5) C18 0.025(8) 0.049(9) 0.029(8) 0.010(6) 0.011(6) -0.003(6) C17 0.052(11) 0.107(15) 0.049(10) 0.043(10) -0.018(8) -0.032(10) N5 0.024(8) 0.20(2) 0.035(8) 0.031(10) 0.000(6) -0.035(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 1.960(8) 3_666 ? Cu1 N1 1.966(8) . ? Cu1 Cl2 2.275(3) . ? Cu1 Cl1 2.278(3) . ? N4 C13 1.341(13) . ? N4 C15 1.396(12) . ? N4 Cu1 1.960(8) 3_666 ? N3 C13 1.347(12) . ? N3 C14 1.349(12) . ? N3 C12 1.480(12) . ? C2 C3 1.360(13) . ? C2 N1 1.395(12) . ? N1 C1 1.326(12) . ? C1 N2 1.368(12) . ? C1 C4 1.478(14) . ? C15 C14 1.315(13) . ? N2 C3 1.396(12) . ? N2 C5 1.486(12) . ? C13 C16 1.492(15) . ? C5 C6 1.517(13) . ? C7 C6 1.388(14) . ? C7 C8 1.394(14) . ? C12 C9 1.524(13) . ? C10 C9 1.363(14) . ? C10 C11 1.375(13) . ? C6 C11 1.412(14) . ? C9 C8 1.409(14) . ? C18 N5 1.132(16) . ? C18 C17 1.420(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cu1 N1 145.1(3) 3_666 . ? N4 Cu1 Cl2 96.0(3) 3_666 . ? N1 Cu1 Cl2 100.1(3) . . ? N4 Cu1 Cl1 98.4(3) 3_666 . ? N1 Cu1 Cl1 97.2(3) . . ? Cl2 Cu1 Cl1 125.18(10) . . ? C13 N4 C15 105.3(8) . . ? C13 N4 Cu1 125.7(7) . 3_666 ? C15 N4 Cu1 128.9(7) . 3_666 ? C13 N3 C14 108.3(8) . . ? C13 N3 C12 125.9(8) . . ? C14 N3 C12 125.7(8) . . ? C3 C2 N1 110.2(9) . . ? C1 N1 C2 106.4(8) . . ? C1 N1 Cu1 127.2(7) . . ? C2 N1 Cu1 126.0(7) . . ? N1 C1 N2 110.1(9) . . ? N1 C1 C4 127.1(9) . . ? N2 C1 C4 122.8(9) . . ? C14 C15 N4 109.3(9) . . ? C1 N2 C3 108.1(8) . . ? C1 N2 C5 127.0(8) . . ? C3 N2 C5 124.0(8) . . ? N4 C13 N3 109.2(9) . . ? N4 C13 C16 125.5(9) . . ? N3 C13 C16 125.3(9) . . ? N2 C5 C6 114.4(8) . . ? C6 C7 C8 120.0(10) . . ? C2 C3 N2 105.3(8) . . ? N3 C12 C9 112.1(8) . . ? C9 C10 C11 121.2(10) . . ? C7 C6 C11 118.5(9) . . ? C7 C6 C5 121.7(9) . . ? C11 C6 C5 119.4(9) . . ? C15 C14 N3 107.9(8) . . ? C10 C9 C8 119.1(9) . . ? C10 C9 C12 121.3(9) . . ? C8 C9 C12 119.6(9) . . ? C7 C8 C9 120.4(10) . . ? C10 C11 C6 120.6(9) . . ? N5 C18 C17 175.5(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C2 N1 C1 -1.6(11) . . . . ? C3 C2 N1 Cu1 171.8(7) . . . . ? N4 Cu1 N1 C1 -71.3(11) 3_666 . . . ? Cl2 Cu1 N1 C1 44.9(9) . . . . ? Cl1 Cu1 N1 C1 172.7(8) . . . . ? N4 Cu1 N1 C2 116.7(8) 3_666 . . . ? Cl2 Cu1 N1 C2 -127.1(7) . . . . ? Cl1 Cu1 N1 C2 0.6(8) . . . . ? C2 N1 C1 N2 1.0(11) . . . . ? Cu1 N1 C1 N2 -172.3(6) . . . . ? C2 N1 C1 C4 -176.8(11) . . . . ? Cu1 N1 C1 C4 9.9(16) . . . . ? C13 N4 C15 C14 1.4(11) . . . . ? Cu1 N4 C15 C14 -179.9(7) 3_666 . . . ? N1 C1 N2 C3 -0.1(11) . . . . ? C4 C1 N2 C3 177.8(10) . . . . ? N1 C1 N2 C5 169.1(9) . . . . ? C4 C1 N2 C5 -12.9(16) . . . . ? C15 N4 C13 N3 -0.9(10) . . . . ? Cu1 N4 C13 N3 -179.7(6) 3_666 . . . ? C15 N4 C13 C16 178.9(10) . . . . ? Cu1 N4 C13 C16 0.1(14) 3_666 . . . ? C14 N3 C13 N4 0.2(11) . . . . ? C12 N3 C13 N4 177.3(8) . . . . ? C14 N3 C13 C16 -179.6(10) . . . . ? C12 N3 C13 C16 -2.6(15) . . . . ? C1 N2 C5 C6 75.9(13) . . . . ? C3 N2 C5 C6 -116.5(10) . . . . ? N1 C2 C3 N2 1.5(11) . . . . ? C1 N2 C3 C2 -0.9(11) . . . . ? C5 N2 C3 C2 -170.5(8) . . . . ? C13 N3 C12 C9 -78.6(12) . . . . ? C14 N3 C12 C9 98.0(11) . . . . ? C8 C7 C6 C11 3.8(14) . . . . ? C8 C7 C6 C5 176.2(9) . . . . ? N2 C5 C6 C7 76.7(12) . . . . ? N2 C5 C6 C11 -110.9(10) . . . . ? N4 C15 C14 N3 -1.3(12) . . . . ? C13 N3 C14 C15 0.7(11) . . . . ? C12 N3 C14 C15 -176.4(9) . . . . ? C11 C10 C9 C8 -1.3(14) . . . . ? C11 C10 C9 C12 178.0(9) . . . . ? N3 C12 C9 C10 112.6(10) . . . . ? N3 C12 C9 C8 -68.1(11) . . . . ? C6 C7 C8 C9 -2.8(15) . . . . ? C10 C9 C8 C7 1.5(14) . . . . ? C12 C9 C8 C7 -177.9(9) . . . . ? C9 C10 C11 C6 2.4(15) . . . . ? C7 C6 C11 C10 -3.6(14) . . . . ? C5 C6 C11 C10 -176.3(9) . . . . ? _diffrn_measured_fraction_theta_max 0.869 _diffrn_reflns_theta_full 28.01 _diffrn_measured_fraction_theta_full 0.869 _refine_diff_density_max 1.608 _refine_diff_density_min -1.160 _refine_diff_density_rms 0.197 data_1 _database_code_depnum_ccdc_archive 'CCDC 635643' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 10 _chemical_melting_point ? _chemical_formula_moiety 'C19 H25 Cl2 Cu N5 O, C3 H7 N O' _chemical_formula_sum 'C22 H32 Cl2 Cu N6 O2' _chemical_formula_weight 546.98 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' 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.8579(11) _cell_length_b 14.7460(13) _cell_length_c 13.8823(12) _cell_angle_alpha 90.00 _cell_angle_beta 98.669(2) _cell_angle_gamma 90.00 _cell_volume 2602.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 303(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1140 _exptl_absorpt_coefficient_mu 1.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7901 _exptl_absorpt_correction_T_max 0.8819 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 303(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16123 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_sigmaI/netI 0.0795 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 28.28 _reflns_number_total 5982 _reflns_number_gt 3428 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _computing_publication_material X-Seed _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^)+(0.1055P)^2^+2.7402P] 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 5982 _refine_ls_number_parameters 304 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.1436 _refine_ls_R_factor_gt 0.0837 _refine_ls_wR_factor_ref 0.2273 _refine_ls_wR_factor_gt 0.1932 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.43013(5) 0.22090(5) 0.37125(4) 0.0435(2) Uani 1 1 d . . . Cl1 Cl 0.34572(12) 0.08249(11) 0.38971(12) 0.0625(5) Uani 1 1 d . . . N1 N 0.3677(4) 0.2312(3) 0.2315(3) 0.0472(11) Uani 1 1 d . . . Cl2 Cl 0.58188(12) 0.28628(13) 0.33467(13) 0.0716(5) Uani 1 1 d . . . C2 C 0.3516(4) 0.3066(4) 0.1791(4) 0.0455(14) Uani 1 1 d . . . N3 N 0.3184(4) 0.2849(4) 0.0846(3) 0.0551(13) Uani 1 1 d . . . C4 C 0.3153(5) 0.1926(5) 0.0775(4) 0.0599(17) Uani 1 1 d . . . H4 H 0.2962 0.1589 0.0210 0.072 Uiso 1 1 calc R . . C5 C 0.3451(5) 0.1594(5) 0.1682(4) 0.0577(16) Uani 1 1 d . . . H5 H 0.3497 0.0983 0.1850 0.069 Uiso 1 1 calc R . . C6 C 0.3658(5) 0.3995(4) 0.2164(4) 0.0590(16) Uani 1 1 d . . . H6A H 0.3740 0.3986 0.2863 0.088 Uiso 1 1 calc R . . H6B H 0.3053 0.4352 0.1913 0.088 Uiso 1 1 calc R . . H6C H 0.4274 0.4255 0.1960 0.088 Uiso 1 1 calc R . . C7 C 0.2912(5) 0.3465(5) 0.0023(4) 0.0630(18) Uani 1 1 d . . . H7A H 0.2872 0.4080 0.0264 0.076 Uiso 1 1 calc R . . H7B H 0.2225 0.3305 -0.0325 0.076 Uiso 1 1 calc R . . C8 C 0.3715(4) 0.3425(5) -0.0669(4) 0.0534(15) Uani 1 1 d . . . C9 C 0.4710(5) 0.3789(5) -0.0421(4) 0.0596(16) Uani 1 1 d . . . H9 H 0.4889 0.4083 0.0174 0.072 Uiso 1 1 calc R . . C10 C 0.5441(5) 0.3719(5) -0.1054(4) 0.0577(16) Uani 1 1 d . . . H10 H 0.6107 0.3967 -0.0876 0.069 Uiso 1 1 calc R . . C11 C 0.5207(4) 0.3292(5) -0.1938(4) 0.0513(14) Uani 1 1 d . . . C12 C 0.4219(5) 0.2946(5) -0.2183(5) 0.070(2) Uani 1 1 d . . . H12 H 0.4040 0.2664 -0.2785 0.084 Uiso 1 1 calc R . . C13 C 0.3471(5) 0.3004(5) -0.1558(4) 0.072(2) Uani 1 1 d . . . H13 H 0.2805 0.2757 -0.1742 0.086 Uiso 1 1 calc R . . C14 C 0.6048(5) 0.3220(5) -0.2582(4) 0.0613(17) Uani 1 1 d . . . H14A H 0.6222 0.3824 -0.2785 0.074 Uiso 1 1 calc R . . H14B H 0.6677 0.2961 -0.2210 0.074 Uiso 1 1 calc R . . N15 N 0.5724(4) 0.2661(4) -0.3450(3) 0.0508(12) Uani 1 1 d . . . C16 C 0.5200(4) 0.2938(4) -0.4317(4) 0.0469(14) Uani 1 1 d . . . N17 N 0.4930(4) 0.2222(3) -0.4880(3) 0.0462(11) Uani 1 1 d . . . C18 C 0.5310(4) 0.1472(4) -0.4355(4) 0.0497(14) Uani 1 1 d . . . H18 H 0.5249 0.0875 -0.4573 0.060 Uiso 1 1 calc R . . C19 C 0.5783(4) 0.1745(5) -0.3476(4) 0.0541(15) Uani 1 1 d . . . H19 H 0.6095 0.1372 -0.2974 0.065 Uiso 1 1 calc R . . C20 C 0.4987(6) 0.3896(5) -0.4572(5) 0.074(2) Uani 1 1 d . . . H20A H 0.5640 0.4210 -0.4576 0.111 Uiso 1 1 calc R . . H20B H 0.4610 0.4169 -0.4100 0.111 Uiso 1 1 calc R . . H20C H 0.4572 0.3933 -0.5206 0.111 Uiso 1 1 calc R . . O21 O 0.2920(4) 0.3121(3) 0.4048(3) 0.0703(13) Uani 1 1 d . . . C22 C 0.2459(7) 0.2944(6) 0.4714(6) 0.0839(19) Uani 1 1 d U . . H22 H 0.2709 0.2446 0.5091 0.101 Uiso 1 1 calc R . . N23 N 0.1645(6) 0.3364(6) 0.4979(5) 0.100(2) Uani 1 1 d U . . C24 C 0.1203(9) 0.4091(7) 0.4375(8) 0.126(2) Uani 1 1 d U . . H24A H 0.1642 0.4618 0.4496 0.189 Uiso 1 1 calc R . . H24B H 0.0512 0.4226 0.4518 0.189 Uiso 1 1 calc R . . H24C H 0.1157 0.3918 0.3703 0.189 Uiso 1 1 calc R . . C25 C 0.1172(8) 0.3088(7) 0.5837(7) 0.115(2) Uani 1 1 d U . . H25A H 0.1440 0.2504 0.6058 0.172 Uiso 1 1 calc R . . H25B H 0.0422 0.3056 0.5665 0.172 Uiso 1 1 calc R . . H25C H 0.1348 0.3525 0.6349 0.172 Uiso 1 1 calc R . . C27 C 0.2821(16) 0.0488(12) -0.1964(11) 0.317(14) Uani 1 1 d DU . . H27 H 0.2155 0.0705 -0.1905 0.380 Uiso 1 1 calc R . . N28 N 0.2996(9) 0.0353(5) -0.2760(7) 0.124(2) Uani 1 1 d U . . C29 C 0.3872(10) -0.0166(8) -0.2960(9) 0.143(3) Uani 1 1 d U . . H29A H 0.4448 -0.0089 -0.2440 0.214 Uiso 1 1 calc R . . H29B H 0.4078 0.0037 -0.3561 0.214 Uiso 1 1 calc R . . H29C H 0.3680 -0.0795 -0.3015 0.214 Uiso 1 1 calc R . . C30 C 0.2253(10) 0.0719(9) -0.3589(9) 0.150(3) Uani 1 1 d U . . H30A H 0.2246 0.0331 -0.4145 0.225 Uiso 1 1 calc R . . H30B H 0.2471 0.1317 -0.3745 0.225 Uiso 1 1 calc R . . H30C H 0.1559 0.0747 -0.3414 0.225 Uiso 1 1 calc R . . O26 O 0.342(2) 0.0374(13) -0.1220(9) 0.55(2) Uani 1 1 d DU . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0387(4) 0.0558(5) 0.0367(4) 0.0055(3) 0.0082(3) -0.0009(3) Cl1 0.0566(9) 0.0621(10) 0.0658(10) 0.0127(8) -0.0001(7) -0.0096(8) N1 0.040(2) 0.064(3) 0.039(2) 0.000(2) 0.010(2) -0.001(2) Cl2 0.0408(8) 0.1079(15) 0.0674(10) 0.0285(10) 0.0124(7) -0.0056(8) C2 0.036(3) 0.064(4) 0.036(3) 0.001(3) 0.006(2) 0.002(3) N3 0.046(3) 0.083(4) 0.038(3) 0.000(3) 0.012(2) 0.003(3) C4 0.055(4) 0.085(5) 0.043(3) -0.013(3) 0.016(3) -0.005(3) C5 0.059(4) 0.065(4) 0.053(4) -0.010(3) 0.020(3) -0.002(3) C6 0.066(4) 0.065(4) 0.044(3) 0.009(3) 0.005(3) 0.004(3) C7 0.048(3) 0.108(6) 0.033(3) 0.013(3) 0.007(2) 0.013(4) C8 0.036(3) 0.087(5) 0.038(3) 0.008(3) 0.007(2) 0.003(3) C9 0.052(4) 0.085(5) 0.043(3) -0.008(3) 0.007(3) -0.002(3) C10 0.042(3) 0.080(5) 0.050(3) -0.002(3) 0.006(3) -0.016(3) C11 0.035(3) 0.080(4) 0.038(3) -0.001(3) 0.005(2) -0.006(3) C12 0.049(4) 0.121(6) 0.042(3) -0.017(4) 0.012(3) -0.023(4) C13 0.041(3) 0.135(7) 0.040(3) -0.008(4) 0.009(3) -0.022(4) C14 0.041(3) 0.102(5) 0.042(3) -0.012(3) 0.010(3) -0.016(3) N15 0.040(3) 0.074(4) 0.040(2) 0.002(2) 0.010(2) -0.007(2) C16 0.044(3) 0.057(4) 0.041(3) 0.007(3) 0.010(2) -0.001(3) N17 0.048(3) 0.051(3) 0.040(2) 0.006(2) 0.008(2) 0.001(2) C18 0.047(3) 0.051(4) 0.052(3) 0.012(3) 0.009(3) 0.002(3) C19 0.041(3) 0.076(5) 0.045(3) 0.018(3) 0.004(3) 0.005(3) C20 0.087(5) 0.060(4) 0.072(4) -0.003(4) 0.000(4) -0.006(4) O21 0.078(3) 0.085(3) 0.052(3) 0.009(2) 0.024(2) 0.019(3) C22 0.075(5) 0.097(5) 0.078(5) -0.018(4) 0.004(3) -0.017(3) N23 0.102(5) 0.122(5) 0.075(4) -0.023(3) 0.011(3) 0.012(4) C24 0.127(3) 0.126(3) 0.126(3) 0.0017(19) 0.018(2) 0.0140(19) C25 0.112(3) 0.122(3) 0.116(3) -0.0083(18) 0.033(2) -0.001(2) C27 0.56(3) 0.27(2) 0.137(4) 0.091(13) 0.123(10) 0.30(2) N28 0.185(7) 0.071(5) 0.119(4) 0.008(4) 0.035(4) 0.003(4) C29 0.143(3) 0.143(3) 0.144(4) 0.001(2) 0.025(2) -0.0015(19) C30 0.151(3) 0.149(4) 0.148(3) 0.001(2) 0.0161(19) 0.002(2) O26 1.07(5) 0.42(3) 0.125(6) -0.008(12) -0.037(16) 0.47(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 N1 1.991(4) . ? Cu1 N17 1.999(4) 1_556 ? Cu1 Cl2 2.3007(16) . ? Cu1 O21 2.331(5) . ? Cu1 Cl1 2.3438(17) . ? N1 C2 1.328(7) . ? N1 C5 1.378(7) . ? C2 N3 1.356(7) . ? C2 C6 1.466(8) . ? N3 C4 1.364(8) . ? N3 C7 1.460(8) . ? C4 C5 1.351(9) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.514(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C13 1.375(8) . ? C8 C9 1.382(8) . ? C9 C10 1.384(8) . ? C9 H9 0.9300 . ? C10 C11 1.371(8) . ? C10 H10 0.9300 . ? C11 C12 1.363(8) . ? C11 C14 1.508(8) . ? C12 C13 1.392(8) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 N15 1.467(7) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? N15 C16 1.351(7) . ? N15 C19 1.353(8) . ? C16 N17 1.328(7) . ? C16 C20 1.471(9) . ? N17 C18 1.373(7) . ? N17 Cu1 1.999(4) 1_554 ? C18 C19 1.342(8) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? O21 C22 1.200(9) . ? C22 N23 1.316(10) . ? C22 H22 0.9300 . ? N23 C24 1.426(11) . ? N23 C25 1.474(11) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C27 N28 1.177(16) . ? C27 O26 1.20(2) . ? C27 H27 0.9300 . ? N28 C29 1.423(13) . ? N28 C30 1.483(13) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 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 N1 Cu1 N17 175.1(2) . 1_556 ? N1 Cu1 Cl2 89.08(14) . . ? N17 Cu1 Cl2 88.85(14) 1_556 . ? N1 Cu1 O21 86.75(17) . . ? N17 Cu1 O21 90.41(17) 1_556 . ? Cl2 Cu1 O21 119.97(14) . . ? N1 Cu1 Cl1 92.71(15) . . ? N17 Cu1 Cl1 91.58(14) 1_556 . ? Cl2 Cu1 Cl1 144.21(7) . . ? O21 Cu1 Cl1 95.82(13) . . ? C2 N1 C5 107.1(5) . . ? C2 N1 Cu1 127.1(4) . . ? C5 N1 Cu1 125.3(4) . . ? N1 C2 N3 109.4(5) . . ? N1 C2 C6 126.1(5) . . ? N3 C2 C6 124.5(5) . . ? C2 N3 C4 107.9(5) . . ? C2 N3 C7 127.8(6) . . ? C4 N3 C7 124.3(5) . . ? C5 C4 N3 107.1(6) . . ? C5 C4 H4 126.5 . . ? N3 C4 H4 126.5 . . ? C4 C5 N1 108.5(6) . . ? C4 C5 H5 125.7 . . ? N1 C5 H5 125.7 . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N3 C7 C8 111.5(5) . . ? N3 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? N3 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C13 C8 C9 118.5(5) . . ? C13 C8 C7 120.1(5) . . ? C9 C8 C7 121.4(5) . . ? C8 C9 C10 120.3(6) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 121.6(5) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C12 C11 C10 117.8(5) . . ? C12 C11 C14 123.4(5) . . ? C10 C11 C14 118.8(5) . . ? C11 C12 C13 121.8(6) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? C8 C13 C12 120.1(6) . . ? C8 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? N15 C14 C11 112.7(5) . . ? N15 C14 H14A 109.0 . . ? C11 C14 H14A 109.0 . . ? N15 C14 H14B 109.0 . . ? C11 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C16 N15 C19 107.5(5) . . ? C16 N15 C14 127.1(6) . . ? C19 N15 C14 124.9(5) . . ? N17 C16 N15 109.6(5) . . ? N17 C16 C20 126.8(5) . . ? N15 C16 C20 123.7(6) . . ? C16 N17 C18 106.8(5) . . ? C16 N17 Cu1 127.9(4) . 1_554 ? C18 N17 Cu1 124.7(4) . 1_554 ? C19 C18 N17 108.4(6) . . ? C19 C18 H18 125.8 . . ? N17 C18 H18 125.8 . . ? C18 C19 N15 107.7(5) . . ? C18 C19 H19 126.1 . . ? N15 C19 H19 126.1 . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 O21 Cu1 120.5(5) . . ? O21 C22 N23 128.2(9) . . ? O21 C22 H22 115.9 . . ? N23 C22 H22 115.9 . . ? C22 N23 C24 116.9(8) . . ? C22 N23 C25 122.6(9) . . ? C24 N23 C25 120.4(8) . . ? N23 C24 H24A 109.5 . . ? N23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N23 C25 H25A 109.5 . . ? N23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N28 C27 O26 126.7(19) . . ? N28 C27 H27 116.7 . . ? O26 C27 H27 116.7 . . ? C27 N28 C29 122.9(12) . . ? C27 N28 C30 118.4(12) . . ? C29 N28 C30 118.7(10) . . ? N28 C29 H29A 109.5 . . ? N28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N28 C30 H30A 109.5 . . ? N28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 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 Cl2 Cu1 N1 C2 -60.3(4) . . . . ? O21 Cu1 N1 C2 59.8(4) . . . . ? Cl1 Cu1 N1 C2 155.5(4) . . . . ? Cl2 Cu1 N1 C5 111.1(4) . . . . ? O21 Cu1 N1 C5 -128.8(4) . . . . ? Cl1 Cu1 N1 C5 -33.1(4) . . . . ? C5 N1 C2 N3 0.7(6) . . . . ? Cu1 N1 C2 N3 173.4(3) . . . . ? C5 N1 C2 C6 179.9(6) . . . . ? Cu1 N1 C2 C6 -7.4(8) . . . . ? N1 C2 N3 C4 -1.0(6) . . . . ? C6 C2 N3 C4 179.7(6) . . . . ? N1 C2 N3 C7 179.7(5) . . . . ? C6 C2 N3 C7 0.4(9) . . . . ? C2 N3 C4 C5 0.9(6) . . . . ? C7 N3 C4 C5 -179.8(5) . . . . ? N3 C4 C5 N1 -0.5(7) . . . . ? C2 N1 C5 C4 -0.1(6) . . . . ? Cu1 N1 C5 C4 -172.9(4) . . . . ? C2 N3 C7 C8 110.2(7) . . . . ? C4 N3 C7 C8 -69.0(8) . . . . ? N3 C7 C8 C13 106.8(7) . . . . ? N3 C7 C8 C9 -71.9(9) . . . . ? C13 C8 C9 C10 -0.7(10) . . . . ? C7 C8 C9 C10 178.0(6) . . . . ? C8 C9 C10 C11 0.1(10) . . . . ? C9 C10 C11 C12 0.9(10) . . . . ? C9 C10 C11 C14 -178.6(6) . . . . ? C10 C11 C12 C13 -1.2(11) . . . . ? C14 C11 C12 C13 178.2(7) . . . . ? C9 C8 C13 C12 0.4(11) . . . . ? C7 C8 C13 C12 -178.3(7) . . . . ? C11 C12 C13 C8 0.6(12) . . . . ? C12 C11 C14 N15 -5.9(10) . . . . ? C10 C11 C14 N15 173.6(6) . . . . ? C11 C14 N15 C16 87.5(7) . . . . ? C11 C14 N15 C19 -83.3(7) . . . . ? C19 N15 C16 N17 0.0(6) . . . . ? C14 N15 C16 N17 -172.1(5) . . . . ? C19 N15 C16 C20 -179.3(6) . . . . ? C14 N15 C16 C20 8.6(9) . . . . ? N15 C16 N17 C18 -0.8(6) . . . . ? C20 C16 N17 C18 178.5(6) . . . . ? N15 C16 N17 Cu1 -171.9(4) . . . 1_554 ? C20 C16 N17 Cu1 7.4(9) . . . 1_554 ? C16 N17 C18 C19 1.3(6) . . . . ? Cu1 N17 C18 C19 172.7(4) 1_554 . . . ? N17 C18 C19 N15 -1.3(6) . . . . ? C16 N15 C19 C18 0.8(6) . . . . ? C14 N15 C19 C18 173.1(5) . . . . ? N1 Cu1 O21 C22 136.4(6) . . . . ? N17 Cu1 O21 C22 -47.6(6) 1_556 . . . ? Cl2 Cu1 O21 C22 -136.5(5) . . . . ? Cl1 Cu1 O21 C22 44.0(6) . . . . ? Cu1 O21 C22 N23 -177.3(6) . . . . ? O21 C22 N23 C24 4.1(13) . . . . ? O21 C22 N23 C25 -178.1(8) . . . . ? O26 C27 N28 C29 15(3) . . . . ? O26 C27 N28 C30 -167(2) . . . . ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.651 _refine_diff_density_min -0.717 _refine_diff_density_rms 0.094 # Attachment '34.CIF' data_2 _database_code_depnum_ccdc_archive 'CCDC 635644' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 3 _chemical_melting_point ? _chemical_formula_moiety 'C32 H36 Cl4 Cu2 N8, 2(C H2 Cl2)' _chemical_formula_sum 'C34 H40 Cl8 Cu2 N8' _chemical_formula_weight 971.42 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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.598(3) _cell_length_b 13.177(4) _cell_length_c 18.105(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.181(6) _cell_angle_gamma 90.00 _cell_volume 2042.9(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow-brownish _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 988 _exptl_absorpt_coefficient_mu 1.601 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7096 _exptl_absorpt_correction_T_max 0.9842 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12610 _diffrn_reflns_av_R_equivalents 0.0900 _diffrn_reflns_av_sigmaI/netI 0.1288 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 28.25 _reflns_number_total 4733 _reflns_number_gt 2851 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _computing_publication_material ? _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^)+(0.0481P)^2^] 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 4733 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1200 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.1307 _refine_ls_wR_factor_gt 0.1108 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _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 0.19622(6) 0.30137(4) 0.40129(3) 0.01418(16) Uani 1 1 d . . . Cl1 Cl -0.02446(13) 0.34904(9) 0.45035(7) 0.0212(3) Uani 1 1 d . . . N1 N 0.1032(4) 0.1848(3) 0.3447(2) 0.0170(9) Uani 1 1 d . . . Cl2 Cl 0.32679(13) 0.37220(9) 0.31054(7) 0.0167(3) Uani 1 1 d . . . C2 C 0.1723(6) 0.1186(3) 0.3028(3) 0.0166(11) Uani 1 1 d . . . Cl3 Cl 0.34567(18) 0.10889(13) 0.59599(9) 0.0458(4) Uani 1 1 d . . . N3 N 0.0665(4) 0.0516(3) 0.2724(2) 0.0155(9) Uani 1 1 d . . . Cl4 Cl 0.22750(18) -0.01258(11) 0.46841(9) 0.0399(4) Uani 1 1 d . . . C4 C -0.0765(5) 0.0752(4) 0.2967(3) 0.0181(11) Uani 1 1 d . . . H4 H -0.1723 0.0404 0.2848 0.022 Uiso 1 1 calc R . . C5 C -0.0540(5) 0.1574(3) 0.3405(3) 0.0162(11) Uani 1 1 d . . . H5 H -0.1326 0.1914 0.3648 0.019 Uiso 1 1 calc R . . C6 C 0.3416(6) 0.1122(4) 0.2920(3) 0.0241(13) Uani 1 1 d . . . H6A H 0.3948 0.1733 0.3121 0.036 Uiso 1 1 calc R . . H6B H 0.3546 0.1067 0.2389 0.036 Uiso 1 1 calc R . . H6C H 0.3868 0.0523 0.3179 0.036 Uiso 1 1 calc R . . C7 C 0.0956(5) -0.0367(3) 0.2258(3) 0.0166(11) Uani 1 1 d . . . H7A H 0.1776 -0.0194 0.1929 0.020 Uiso 1 1 calc R . . H7B H -0.0010 -0.0534 0.1942 0.020 Uiso 1 1 calc R . . C8 C 0.1469(5) -0.1284(3) 0.2721(3) 0.0138(10) Uani 1 1 d . . . C9 C 0.3011(6) -0.1617(4) 0.2770(3) 0.0183(11) Uani 1 1 d . . . H9 H 0.3752 -0.1278 0.2499 0.022 Uiso 1 1 calc R . . C10 C 0.3473(5) -0.2447(4) 0.3215(3) 0.0171(11) Uani 1 1 d . . . H10 H 0.4524 -0.2676 0.3236 0.021 Uiso 1 1 calc R . . C11 C 0.2428(5) -0.2942(3) 0.3626(3) 0.0152(10) Uani 1 1 d . . . C12 C 0.0880(5) -0.2602(4) 0.3575(3) 0.0152(11) Uani 1 1 d . . . H12 H 0.0144 -0.2929 0.3856 0.018 Uiso 1 1 calc R . . C13 C 0.0408(5) -0.1797(4) 0.3120(3) 0.0174(11) Uani 1 1 d . . . H13 H -0.0655 -0.1592 0.3079 0.021 Uiso 1 1 calc R . . C14 C 0.2878(5) -0.3854(4) 0.4100(3) 0.0177(11) Uani 1 1 d . . . H14B H 0.2191 -0.3887 0.4509 0.021 Uiso 1 1 calc R . . H14A H 0.2692 -0.4474 0.3795 0.021 Uiso 1 1 calc R . . N15 N 0.4531(4) -0.3851(3) 0.4420(2) 0.0155(9) Uani 1 1 d . . . C16 C 0.5695(5) -0.4441(3) 0.4177(3) 0.0172(11) Uani 1 1 d . . . H16 H 0.5601 -0.4906 0.3774 0.021 Uiso 1 1 calc R . . C17 C 0.7013(6) -0.4228(4) 0.4626(3) 0.0163(11) Uani 1 1 d . . . H17 H 0.8011 -0.4525 0.4593 0.020 Uiso 1 1 calc R . . N18 N 0.6653(4) -0.3508(3) 0.5139(2) 0.0153(9) Uani 1 1 d . . . C19 C 0.5129(5) -0.3289(3) 0.4998(3) 0.0143(11) Uani 1 1 d . . . C20 C 0.4241(5) -0.2554(4) 0.5412(3) 0.0195(11) Uani 1 1 d . . . H16C H 0.4017 -0.2853 0.5887 0.029 Uiso 1 1 calc R . . H16A H 0.3258 -0.2388 0.5121 0.029 Uiso 1 1 calc R . . H16B H 0.4860 -0.1935 0.5503 0.029 Uiso 1 1 calc R . . C21B C 0.1802(7) 0.0738(4) 0.5371(3) 0.0340(15) Uani 1 1 d . . . H21A H 0.1020 0.0426 0.5670 0.041 Uiso 1 1 calc R . . H21B H 0.1328 0.1352 0.5130 0.041 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0107(3) 0.0164(3) 0.0155(3) -0.0014(3) 0.0015(2) -0.0002(3) Cl1 0.0141(6) 0.0287(7) 0.0211(7) -0.0064(6) 0.0036(5) 0.0007(5) N1 0.014(2) 0.015(2) 0.022(2) 0.0012(18) 0.0045(18) -0.0007(17) Cl2 0.0137(6) 0.0201(6) 0.0166(6) -0.0015(5) 0.0026(5) -0.0020(5) C2 0.019(3) 0.011(2) 0.019(3) -0.001(2) 0.001(2) -0.002(2) Cl3 0.0374(9) 0.0608(11) 0.0386(10) -0.0036(8) -0.0007(8) -0.0182(8) N3 0.018(2) 0.013(2) 0.016(2) 0.0009(17) 0.0000(18) -0.0019(17) Cl4 0.0502(9) 0.0367(9) 0.0316(9) -0.0030(7) -0.0019(8) 0.0101(7) C4 0.014(2) 0.019(3) 0.022(3) 0.005(2) 0.002(2) -0.001(2) C5 0.012(2) 0.014(2) 0.024(3) 0.005(2) 0.006(2) 0.001(2) C6 0.020(3) 0.021(3) 0.032(3) -0.006(2) 0.005(2) -0.005(2) C7 0.018(3) 0.018(3) 0.013(3) -0.004(2) -0.004(2) -0.002(2) C8 0.017(2) 0.013(2) 0.012(2) -0.006(2) -0.002(2) -0.001(2) C9 0.020(3) 0.016(3) 0.020(3) -0.002(2) 0.003(2) -0.005(2) C10 0.009(2) 0.017(3) 0.025(3) -0.007(2) -0.001(2) 0.000(2) C11 0.016(2) 0.014(2) 0.015(3) -0.006(2) -0.001(2) -0.005(2) C12 0.013(2) 0.019(3) 0.014(3) -0.005(2) 0.003(2) -0.003(2) C13 0.011(2) 0.023(3) 0.018(3) -0.002(2) 0.001(2) 0.002(2) C14 0.013(2) 0.021(3) 0.019(3) -0.004(2) 0.000(2) -0.006(2) N15 0.012(2) 0.014(2) 0.020(2) 0.0005(18) 0.0009(18) 0.0025(17) C16 0.020(3) 0.014(3) 0.018(3) -0.003(2) 0.002(2) 0.006(2) C17 0.015(2) 0.018(3) 0.017(3) -0.001(2) 0.007(2) 0.004(2) N18 0.016(2) 0.015(2) 0.015(2) -0.0010(18) 0.0011(18) 0.0001(17) C19 0.014(2) 0.013(2) 0.016(3) -0.004(2) -0.003(2) -0.0013(19) C20 0.014(2) 0.020(3) 0.023(3) -0.003(2) -0.004(2) 0.004(2) C21B 0.037(3) 0.034(3) 0.030(4) 0.000(3) -0.001(3) -0.002(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 N18 1.967(4) 3_656 ? Cu1 N1 1.976(4) . ? Cu1 Cl1 2.2555(14) . ? Cu1 Cl2 2.2725(14) . ? N1 C2 1.330(6) . ? N1 C5 1.394(6) . ? C2 N3 1.350(6) . ? C2 C6 1.488(6) . ? Cl3 C21B 1.761(6) . ? N3 C4 1.379(6) . ? N3 C7 1.471(6) . ? Cl4 C21B 1.761(6) . ? C4 C5 1.347(7) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.513(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C13 1.389(6) . ? C8 C9 1.392(6) . ? C9 C10 1.395(7) . ? C9 H9 0.9500 . ? C10 C11 1.381(6) . ? C10 H10 0.9500 . ? C11 C12 1.399(6) . ? C11 C14 1.507(7) . ? C12 C13 1.381(6) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 N15 1.486(6) . ? C14 H14B 0.9900 . ? C14 H14A 0.9900 . ? N15 C19 1.345(6) . ? N15 C16 1.371(5) . ? C16 C17 1.363(6) . ? C16 H16 0.9500 . ? C17 N18 1.382(6) . ? C17 H17 0.9500 . ? N18 C19 1.344(6) . ? N18 Cu1 1.967(4) 3_656 ? C19 C20 1.479(6) . ? C20 H16C 0.9800 . ? C20 H16A 0.9800 . ? C20 H16B 0.9800 . ? C21B H21A 0.9900 . ? C21B H21B 0.9900 . ? 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 N18 Cu1 N1 148.27(16) 3_656 . ? N18 Cu1 Cl1 94.12(12) 3_656 . ? N1 Cu1 Cl1 96.05(12) . . ? N18 Cu1 Cl2 97.16(12) 3_656 . ? N1 Cu1 Cl2 98.50(12) . . ? Cl1 Cu1 Cl2 131.17(5) . . ? C2 N1 C5 106.3(4) . . ? C2 N1 Cu1 128.6(3) . . ? C5 N1 Cu1 125.0(3) . . ? N1 C2 N3 110.0(4) . . ? N1 C2 C6 127.3(4) . . ? N3 C2 C6 122.7(4) . . ? C2 N3 C4 108.1(4) . . ? C2 N3 C7 127.5(4) . . ? C4 N3 C7 124.3(4) . . ? C5 C4 N3 106.5(4) . . ? C5 C4 H4 126.7 . . ? N3 C4 H4 126.7 . . ? C4 C5 N1 109.1(4) . . ? C4 C5 H5 125.5 . . ? N1 C5 H5 125.5 . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N3 C7 C8 111.7(4) . . ? N3 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? N3 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C13 C8 C9 118.7(4) . . ? C13 C8 C7 120.3(4) . . ? C9 C8 C7 121.0(4) . . ? C8 C9 C10 120.2(5) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 121.1(4) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 118.3(5) . . ? C10 C11 C14 122.5(4) . . ? C12 C11 C14 119.2(4) . . ? C13 C12 C11 120.8(5) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C8 120.9(4) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? N15 C14 C11 114.1(4) . . ? N15 C14 H14B 108.7 . . ? C11 C14 H14B 108.7 . . ? N15 C14 H14A 108.7 . . ? C11 C14 H14A 108.7 . . ? H14B C14 H14A 107.6 . . ? C19 N15 C16 108.9(4) . . ? C19 N15 C14 126.2(4) . . ? C16 N15 C14 124.9(4) . . ? C17 C16 N15 106.4(4) . . ? C17 C16 H16 126.8 . . ? N15 C16 H16 126.8 . . ? C16 C17 N18 108.6(4) . . ? C16 C17 H17 125.7 . . ? N18 C17 H17 125.7 . . ? C19 N18 C17 107.0(4) . . ? C19 N18 Cu1 126.1(3) . 3_656 ? C17 N18 Cu1 126.5(3) . 3_656 ? N18 C19 N15 109.1(4) . . ? N18 C19 C20 125.7(4) . . ? N15 C19 C20 125.2(4) . . ? C19 C20 H16C 109.5 . . ? C19 C20 H16A 109.5 . . ? H16C C20 H16A 109.5 . . ? C19 C20 H16B 109.5 . . ? H16C C20 H16B 109.5 . . ? H16A C20 H16B 109.5 . . ? Cl4 C21B Cl3 111.8(3) . . ? Cl4 C21B H21A 109.3 . . ? Cl3 C21B H21A 109.3 . . ? Cl4 C21B H21B 109.3 . . ? Cl3 C21B H21B 109.3 . . ? H21A C21B H21B 107.9 . . ? 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 N18 Cu1 N1 C2 -70.2(5) 3_656 . . . ? Cl1 Cu1 N1 C2 -178.1(4) . . . . ? Cl2 Cu1 N1 C2 48.6(4) . . . . ? N18 Cu1 N1 C5 111.1(4) 3_656 . . . ? Cl1 Cu1 N1 C5 3.1(4) . . . . ? Cl2 Cu1 N1 C5 -130.1(4) . . . . ? C5 N1 C2 N3 0.2(5) . . . . ? Cu1 N1 C2 N3 -178.7(3) . . . . ? C5 N1 C2 C6 -176.7(5) . . . . ? Cu1 N1 C2 C6 4.3(7) . . . . ? N1 C2 N3 C4 -0.7(5) . . . . ? C6 C2 N3 C4 176.4(5) . . . . ? N1 C2 N3 C7 -176.6(4) . . . . ? C6 C2 N3 C7 0.5(8) . . . . ? C2 N3 C4 C5 0.9(5) . . . . ? C7 N3 C4 C5 176.9(4) . . . . ? N3 C4 C5 N1 -0.7(5) . . . . ? C2 N1 C5 C4 0.3(5) . . . . ? Cu1 N1 C5 C4 179.3(3) . . . . ? C2 N3 C7 C8 83.8(6) . . . . ? C4 N3 C7 C8 -91.5(5) . . . . ? N3 C7 C8 C13 71.5(5) . . . . ? N3 C7 C8 C9 -107.0(5) . . . . ? C13 C8 C9 C10 -0.3(7) . . . . ? C7 C8 C9 C10 178.2(4) . . . . ? C8 C9 C10 C11 -1.3(7) . . . . ? C9 C10 C11 C12 1.2(7) . . . . ? C9 C10 C11 C14 178.6(4) . . . . ? C10 C11 C12 C13 0.4(7) . . . . ? C14 C11 C12 C13 -177.0(4) . . . . ? C11 C12 C13 C8 -2.1(7) . . . . ? C9 C8 C13 C12 2.0(7) . . . . ? C7 C8 C13 C12 -176.6(4) . . . . ? C10 C11 C14 N15 31.7(7) . . . . ? C12 C11 C14 N15 -150.9(4) . . . . ? C11 C14 N15 C19 76.1(6) . . . . ? C11 C14 N15 C16 -105.0(5) . . . . ? C19 N15 C16 C17 0.5(5) . . . . ? C14 N15 C16 C17 -178.6(4) . . . . ? N15 C16 C17 N18 -0.3(5) . . . . ? C16 C17 N18 C19 -0.1(5) . . . . ? C16 C17 N18 Cu1 173.4(3) . . . 3_656 ? C17 N18 C19 N15 0.4(5) . . . . ? Cu1 N18 C19 N15 -173.1(3) 3_656 . . . ? C17 N18 C19 C20 180.0(5) . . . . ? Cu1 N18 C19 C20 6.5(7) 3_656 . . . ? C16 N15 C19 N18 -0.6(5) . . . . ? C14 N15 C19 N18 178.5(4) . . . . ? C16 N15 C19 C20 179.8(4) . . . . ? C14 N15 C19 C20 -1.1(8) . . . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.717 _refine_diff_density_min -0.594 _refine_diff_density_rms 0.132 data_I _database_code_depnum_ccdc_archive 'CCDC 635645' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4 _chemical_melting_point ? _chemical_formula_moiety 'C40 H52 Cl4 Cu2 N8 O2' _chemical_formula_sum 'C40 H52 Cl4 Cu2 N8 O2' _chemical_formula_weight 945.78 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.826(3) _cell_length_b 13.103(5) _cell_length_c 18.057(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.838(7) _cell_angle_gamma 90.00 _cell_volume 2077.5(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 980 _exptl_absorpt_coefficient_mu 1.327 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8570 _exptl_absorpt_correction_T_max 0.9128 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10633 _diffrn_reflns_av_R_equivalents 0.1379 _diffrn_reflns_av_sigmaI/netI 0.1668 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.09 _reflns_number_total 3662 _reflns_number_gt 2235 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _computing_publication_material X-Seed _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^)+(0.0528P)^2^+1.9679P] 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 3662 _refine_ls_number_parameters 255 _refine_ls_number_restraints 42 _refine_ls_R_factor_all 0.1549 _refine_ls_R_factor_gt 0.0908 _refine_ls_wR_factor_ref 0.1706 _refine_ls_wR_factor_gt 0.1486 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.004 _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 0.28477(11) 0.19855(8) 0.10362(5) 0.0120(3) Uani 1 1 d . . . Cl2 Cl 0.1752(2) 0.11457(15) 0.19795(11) 0.0138(5) Uani 1 1 d . . . Cl3 Cl 0.4964(2) 0.15459(17) 0.04883(11) 0.0203(5) Uani 1 1 d . . . N1 N 0.3860(7) 0.3029(5) 0.1684(3) 0.0137(15) Uani 1 1 d . . . N17 N -0.1434(7) 0.8556(5) -0.0221(3) 0.0111(15) Uani 1 1 d . . . N15 N 0.0657(7) 0.8836(5) 0.0513(3) 0.0116(15) Uani 1 1 d . . . C11 C 0.2613(9) 0.7852(6) 0.1315(4) 0.0133(19) Uani 1 1 d . . . C5 C 0.5393(9) 0.3279(6) 0.1737(4) 0.0129(19) Uani 1 1 d U . . H5 H 0.6157 0.2920 0.1509 0.015 Uiso 1 1 calc R . . N3 N 0.4243(8) 0.4399(5) 0.2377(3) 0.0126(16) Uani 1 1 d . . . C14 C 0.2241(9) 0.8785(6) 0.0836(4) 0.0132(19) Uani 1 1 d . . . H14A H 0.2474 0.9403 0.1141 0.016 Uiso 1 1 calc R . . H14B H 0.2909 0.8790 0.0427 0.016 Uiso 1 1 calc R . . C16 C 0.0069(9) 0.8374(6) -0.0116(4) 0.0135(19) Uani 1 1 d U . . C12 C 0.4088(9) 0.7439(6) 0.1339(4) 0.0143(19) Uani 1 1 d . . . H12 H 0.4801 0.7715 0.1033 0.017 Uiso 1 1 calc R . . C8 C 0.3465(9) 0.6203(6) 0.2255(4) 0.0124(19) Uani 1 1 d U . . C2 C 0.3195(9) 0.3720(6) 0.2079(4) 0.014(2) Uani 1 1 d . . . C9 C 0.1999(9) 0.6609(6) 0.2211(4) 0.0119(18) Uani 1 1 d U . . H9 H 0.1277 0.6326 0.2509 0.014 Uiso 1 1 calc R . . C6 C 0.1539(9) 0.3802(7) 0.2174(5) 0.020(2) Uani 1 1 d . . . H6A H 0.1130 0.4434 0.1942 0.030 Uiso 1 1 calc R . . H6B H 0.1403 0.3810 0.2706 0.030 Uiso 1 1 calc R . . H6C H 0.0997 0.3216 0.1937 0.030 Uiso 1 1 calc R . . C18 C -0.1780(10) 0.9162(6) 0.0356(4) 0.0140(19) Uani 1 1 d . . . H18 H -0.2764 0.9418 0.0424 0.017 Uiso 1 1 calc R . . C7 C 0.3936(9) 0.5339(6) 0.2780(4) 0.0115(19) Uani 1 1 d . . . H7A H 0.4864 0.5539 0.3102 0.014 Uiso 1 1 calc R . . H7B H 0.3118 0.5209 0.3104 0.014 Uiso 1 1 calc R . . C4 C 0.5618(10) 0.4111(6) 0.2164(4) 0.015(2) Uani 1 1 d U . . H4 H 0.6566 0.4441 0.2295 0.018 Uiso 1 1 calc R . . C10 C 0.1578(9) 0.7418(6) 0.1739(4) 0.0100(18) Uani 1 1 d U . . H10 H 0.0567 0.7673 0.1708 0.012 Uiso 1 1 calc R . . C20 C 0.0952(9) 0.7752(6) -0.0602(4) 0.017(2) Uani 1 1 d U . . H20A H 0.1881 0.7503 -0.0315 0.025 Uiso 1 1 calc R . . H20B H 0.1226 0.8170 -0.1018 0.025 Uiso 1 1 calc R . . H20C H 0.0335 0.7170 -0.0795 0.025 Uiso 1 1 calc R . . C19 C -0.0493(9) 0.9338(6) 0.0817(4) 0.0126(19) Uani 1 1 d . . . H19 H -0.0407 0.9730 0.1262 0.015 Uiso 1 1 calc R . . C13 C 0.4496(9) 0.6629(6) 0.1808(4) 0.0121(19) Uani 1 1 d . . . H13 H 0.5498 0.6359 0.1826 0.015 Uiso 1 1 calc R . . O21 O 0.1823(7) 0.3804(4) 0.0298(3) 0.0224(15) Uani 1 1 d . . . C22 C 0.2726(10) 0.4720(7) 0.0413(4) 0.020(2) Uani 1 1 d . . . H22A H 0.3688 0.4575 0.0727 0.024 Uiso 1 1 calc R . . H22B H 0.2158 0.5251 0.0659 0.024 Uiso 1 1 calc R . . C23 C 0.3050(10) 0.5068(7) -0.0359(5) 0.022(2) Uani 1 1 d . . . H23A H 0.3192 0.5816 -0.0377 0.026 Uiso 1 1 calc R . . H23B H 0.3965 0.4726 -0.0517 0.026 Uiso 1 1 calc R . . C25 C 0.1316(10) 0.3726(7) -0.0485(4) 0.024(2) Uani 1 1 d . . . H25A H 0.0213 0.3570 -0.0557 0.029 Uiso 1 1 calc R . . H25B H 0.1873 0.3175 -0.0716 0.029 Uiso 1 1 calc R . . C24 C 0.1629(10) 0.4742(7) -0.0836(5) 0.026(2) Uani 1 1 d . . . H24A H 0.1816 0.4663 -0.1364 0.031 Uiso 1 1 calc R . . H24B H 0.0783 0.5229 -0.0799 0.031 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0111(6) 0.0104(5) 0.0142(5) -0.0012(5) 0.0001(4) -0.0012(5) Cl2 0.0136(11) 0.0118(10) 0.0159(11) -0.0011(9) 0.0010(9) -0.0013(9) Cl3 0.0133(12) 0.0283(13) 0.0191(11) -0.0070(10) 0.0008(10) -0.0013(10) N1 0.015(4) 0.011(4) 0.017(4) 0.000(3) 0.006(3) 0.000(3) N17 0.009(4) 0.009(4) 0.015(4) -0.002(3) 0.000(3) -0.001(3) N15 0.008(4) 0.010(4) 0.016(4) -0.003(3) 0.000(3) -0.001(3) C11 0.013(5) 0.014(5) 0.013(4) -0.010(4) 0.003(4) -0.005(4) C5 0.012(2) 0.013(2) 0.014(2) 0.0029(18) 0.0024(18) -0.0003(18) N3 0.023(4) 0.004(4) 0.011(4) -0.002(3) 0.000(3) -0.002(3) C14 0.011(5) 0.012(5) 0.017(4) -0.006(4) -0.001(4) -0.002(4) C16 0.013(2) 0.013(2) 0.014(2) 0.0018(18) 0.0002(18) -0.0021(18) C12 0.010(5) 0.020(5) 0.011(4) 0.000(4) -0.005(4) -0.006(4) C8 0.014(2) 0.011(2) 0.013(2) 0.0002(18) 0.0009(18) -0.0001(18) C2 0.014(5) 0.014(5) 0.014(4) 0.006(4) -0.005(4) -0.005(4) C9 0.013(2) 0.011(2) 0.012(2) -0.0014(18) 0.0015(18) -0.0017(18) C6 0.023(5) 0.019(5) 0.017(5) -0.004(4) -0.005(4) -0.005(4) C18 0.014(5) 0.007(4) 0.021(5) 0.004(4) 0.004(4) 0.000(4) C7 0.016(5) 0.006(4) 0.011(4) 0.003(3) -0.003(4) -0.002(3) C4 0.014(3) 0.016(3) 0.015(3) 0.0031(18) 0.0003(18) -0.0012(18) C10 0.009(2) 0.010(2) 0.011(2) -0.0022(18) -0.0007(18) 0.0013(18) C20 0.017(3) 0.016(3) 0.017(3) -0.0018(18) 0.0018(18) 0.0014(18) C19 0.023(5) 0.008(4) 0.008(4) 0.002(3) 0.005(4) -0.005(4) C13 0.014(5) 0.006(4) 0.017(4) 0.000(4) 0.004(4) 0.002(3) O21 0.027(4) 0.020(4) 0.019(3) 0.002(3) -0.001(3) -0.011(3) C22 0.019(5) 0.024(5) 0.015(5) 0.007(4) -0.006(4) -0.006(4) C23 0.016(5) 0.021(5) 0.029(5) 0.008(4) -0.001(4) -0.003(4) C25 0.024(6) 0.023(6) 0.024(5) -0.002(4) -0.007(4) -0.004(4) C24 0.031(6) 0.029(6) 0.017(5) 0.005(4) 0.004(4) -0.009(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 Cu1 N1 1.956(7) . ? Cu1 N17 1.963(6) 3_565 ? Cu1 Cl3 2.275(2) . ? Cu1 Cl2 2.320(2) . ? N1 C2 1.325(10) . ? N1 C5 1.386(10) . ? N17 C16 1.342(10) . ? N17 C18 1.369(10) . ? N17 Cu1 1.963(6) 3_565 ? N15 C16 1.344(9) . ? N15 C19 1.370(10) . ? N15 C14 1.460(10) . ? C11 C10 1.372(10) . ? C11 C12 1.407(11) . ? C11 C14 1.515(11) . ? C5 C4 1.338(11) . ? C5 H5 0.9500 . ? N3 C2 1.354(10) . ? N3 C4 1.364(10) . ? N3 C7 1.470(10) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C16 C20 1.477(11) . ? C12 C13 1.382(10) . ? C12 H12 0.9500 . ? C8 C9 1.393(11) . ? C8 C13 1.394(10) . ? C8 C7 1.508(10) . ? C2 C6 1.493(11) . ? C9 C10 1.387(10) . ? C9 H9 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C18 C19 1.358(11) . ? C18 H18 0.9500 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C4 H4 0.9500 . ? C10 H10 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C19 H19 0.9500 . ? C13 H13 0.9500 . ? O21 C25 1.443(9) . ? O21 C22 1.444(9) . ? C22 C23 1.521(11) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.509(12) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C25 C24 1.511(12) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? 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 Cu1 N17 156.7(3) . 3_565 ? N1 Cu1 Cl3 95.3(2) . . ? N17 Cu1 Cl3 94.0(2) 3_565 . ? N1 Cu1 Cl2 95.24(19) . . ? N17 Cu1 Cl2 95.6(2) 3_565 . ? Cl3 Cu1 Cl2 128.40(9) . . ? C2 N1 C5 106.5(7) . . ? C2 N1 Cu1 126.8(6) . . ? C5 N1 Cu1 126.1(5) . . ? C16 N17 C18 106.8(6) . . ? C16 N17 Cu1 125.8(5) . 3_565 ? C18 N17 Cu1 127.3(5) . 3_565 ? C16 N15 C19 108.5(7) . . ? C16 N15 C14 126.0(7) . . ? C19 N15 C14 125.5(7) . . ? C10 C11 C12 119.4(8) . . ? C10 C11 C14 122.3(7) . . ? C12 C11 C14 118.3(7) . . ? C4 C5 N1 108.6(7) . . ? C4 C5 H5 125.7 . . ? N1 C5 H5 125.7 . . ? C2 N3 C4 107.3(7) . . ? C2 N3 C7 126.5(7) . . ? C4 N3 C7 125.8(7) . . ? N15 C14 C11 114.1(7) . . ? N15 C14 H14A 108.7 . . ? C11 C14 H14A 108.7 . . ? N15 C14 H14B 108.7 . . ? C11 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? N17 C16 N15 109.3(7) . . ? N17 C16 C20 126.0(7) . . ? N15 C16 C20 124.7(7) . . ? C13 C12 C11 119.7(8) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C9 C8 C13 118.1(7) . . ? C9 C8 C7 121.2(7) . . ? C13 C8 C7 120.7(7) . . ? N1 C2 N3 109.9(7) . . ? N1 C2 C6 127.1(7) . . ? N3 C2 C6 123.0(7) . . ? C10 C9 C8 121.1(8) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C19 C18 N17 109.1(7) . . ? C19 C18 H18 125.5 . . ? N17 C18 H18 125.5 . . ? N3 C7 C8 111.8(6) . . ? N3 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? N3 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C5 C4 N3 107.7(7) . . ? C5 C4 H4 126.2 . . ? N3 C4 H4 126.2 . . ? C11 C10 C9 120.5(8) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C19 N15 106.3(7) . . ? C18 C19 H19 126.9 . . ? N15 C19 H19 126.9 . . ? C12 C13 C8 121.2(8) . . ? C12 C13 H13 119.4 . . ? C8 C13 H13 119.4 . . ? C25 O21 C22 108.1(6) . . ? O21 C22 C23 105.7(6) . . ? O21 C22 H22A 110.6 . . ? C23 C22 H22A 110.6 . . ? O21 C22 H22B 110.6 . . ? C23 C22 H22B 110.6 . . ? H22A C22 H22B 108.7 . . ? C24 C23 C22 102.4(7) . . ? C24 C23 H23A 111.3 . . ? C22 C23 H23A 111.3 . . ? C24 C23 H23B 111.3 . . ? C22 C23 H23B 111.3 . . ? H23A C23 H23B 109.2 . . ? O21 C25 C24 107.3(7) . . ? O21 C25 H25A 110.3 . . ? C24 C25 H25A 110.3 . . ? O21 C25 H25B 110.3 . . ? C24 C25 H25B 110.3 . . ? H25A C25 H25B 108.5 . . ? C23 C24 C25 100.8(7) . . ? C23 C24 H24A 111.6 . . ? C25 C24 H24A 111.6 . . ? C23 C24 H24B 111.6 . . ? C25 C24 H24B 111.6 . . ? H24A C24 H24B 109.4 . . ? 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 N17 Cu1 N1 C2 54.8(11) 3_565 . . . ? Cl3 Cu1 N1 C2 167.9(6) . . . . ? Cl2 Cu1 N1 C2 -62.7(7) . . . . ? N17 Cu1 N1 C5 -115.5(8) 3_565 . . . ? Cl3 Cu1 N1 C5 -2.4(6) . . . . ? Cl2 Cu1 N1 C5 127.0(6) . . . . ? C2 N1 C5 C4 0.2(9) . . . . ? Cu1 N1 C5 C4 172.1(5) . . . . ? C16 N15 C14 C11 -84.0(9) . . . . ? C19 N15 C14 C11 93.7(9) . . . . ? C10 C11 C14 N15 -33.7(10) . . . . ? C12 C11 C14 N15 148.0(7) . . . . ? C18 N17 C16 N15 0.9(9) . . . . ? Cu1 N17 C16 N15 -177.5(5) 3_565 . . . ? C18 N17 C16 C20 179.9(7) . . . . ? Cu1 N17 C16 C20 1.5(12) 3_565 . . . ? C19 N15 C16 N17 -0.7(9) . . . . ? C14 N15 C16 N17 177.3(7) . . . . ? C19 N15 C16 C20 -179.7(8) . . . . ? C14 N15 C16 C20 -1.7(13) . . . . ? C10 C11 C12 C13 -2.6(11) . . . . ? C14 C11 C12 C13 175.8(7) . . . . ? C5 N1 C2 N3 0.2(9) . . . . ? Cu1 N1 C2 N3 -171.6(5) . . . . ? C5 N1 C2 C6 177.9(7) . . . . ? Cu1 N1 C2 C6 6.0(12) . . . . ? C4 N3 C2 N1 -0.6(9) . . . . ? C7 N3 C2 N1 172.8(7) . . . . ? C4 N3 C2 C6 -178.3(7) . . . . ? C7 N3 C2 C6 -5.0(12) . . . . ? C13 C8 C9 C10 -0.4(11) . . . . ? C7 C8 C9 C10 178.6(7) . . . . ? C16 N17 C18 C19 -0.7(9) . . . . ? Cu1 N17 C18 C19 177.6(5) 3_565 . . . ? C2 N3 C7 C8 -81.4(9) . . . . ? C4 N3 C7 C8 90.8(9) . . . . ? C9 C8 C7 N3 113.4(8) . . . . ? C13 C8 C7 N3 -67.6(10) . . . . ? N1 C5 C4 N3 -0.6(9) . . . . ? C2 N3 C4 C5 0.7(9) . . . . ? C7 N3 C4 C5 -172.7(7) . . . . ? C12 C11 C10 C9 2.9(11) . . . . ? C14 C11 C10 C9 -175.4(7) . . . . ? C8 C9 C10 C11 -1.4(12) . . . . ? N17 C18 C19 N15 0.3(9) . . . . ? C16 N15 C19 C18 0.2(9) . . . . ? C14 N15 C19 C18 -177.8(7) . . . . ? C11 C12 C13 C8 0.8(12) . . . . ? C9 C8 C13 C12 0.6(12) . . . . ? C7 C8 C13 C12 -178.3(7) . . . . ? C25 O21 C22 C23 -12.8(9) . . . . ? O21 C22 C23 C24 32.9(9) . . . . ? C22 O21 C25 C24 -12.5(9) . . . . ? C22 C23 C24 C25 -38.8(9) . . . . ? O21 C25 C24 C23 32.4(9) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.09 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.841 _refine_diff_density_min -0.839 _refine_diff_density_rms 0.141 # Attachment '53.CIF' data_4 _database_code_depnum_ccdc_archive 'CCDC 635646' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 5 _chemical_melting_point ? _chemical_formula_moiety 'C36 H48 Cl4 Cu2 N8 O2 S2' _chemical_formula_sum 'C36 H48 Cl4 Cu2 N8 O2 S2' _chemical_formula_weight 957.82 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.8822(14) _cell_length_b 13.050(2) _cell_length_c 17.792(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.486(3) _cell_angle_gamma 90.00 _cell_volume 2052.9(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow-greenish _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 988 _exptl_absorpt_coefficient_mu 1.442 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7712 _exptl_absorpt_correction_T_max 0.8127 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12572 _diffrn_reflns_av_R_equivalents 0.0527 _diffrn_reflns_av_sigmaI/netI 0.0726 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 28.24 _reflns_number_total 4724 _reflns_number_gt 3599 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _computing_publication_material 'X-Seed (Barbour 2001)' _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^)+(0.0543P)^2^+0.3198P] 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 4724 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1161 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.27937(5) 0.21929(3) 0.09441(2) 0.01195(12) Uani 1 1 d . . . Cl1 Cl 0.49696(9) 0.16639(7) 0.04405(5) 0.0194(2) Uani 1 1 d . . . N1 N 0.3870(3) 0.3222(2) 0.16072(16) 0.0133(6) Uani 1 1 d . . . Cl2 Cl 0.18014(9) 0.13142(6) 0.19548(5) 0.01421(19) Uani 1 1 d . . . C2 C 0.3221(4) 0.3891(3) 0.20450(19) 0.0133(7) Uani 1 1 d . . . N3 N 0.4263(3) 0.4556(2) 0.23600(15) 0.0120(6) Uani 1 1 d . . . C4 C 0.5638(4) 0.4304(3) 0.21164(19) 0.0156(7) Uani 1 1 d . . . H4 H 0.6578 0.4638 0.2245 0.019 Uiso 1 1 calc R . . C5 C 0.5383(4) 0.3483(3) 0.16554(19) 0.0150(7) Uani 1 1 d . . . H5 H 0.6132 0.3138 0.1403 0.018 Uiso 1 1 calc R . . C6 C 0.1585(4) 0.3934(3) 0.2170(2) 0.0179(8) Uani 1 1 d . . . H6A H 0.1026 0.3426 0.1848 0.027 Uiso 1 1 calc R . . H6B H 0.1190 0.4620 0.2043 0.027 Uiso 1 1 calc R . . H6C H 0.1465 0.3786 0.2701 0.027 Uiso 1 1 calc R . . C7 C 0.3969(4) 0.5463(2) 0.28178(19) 0.0152(7) Uani 1 1 d . . . H7B H 0.4897 0.5643 0.3144 0.018 Uiso 1 1 calc R . . H7A H 0.3165 0.5302 0.3148 0.018 Uiso 1 1 calc R . . C8 C 0.3486(4) 0.6364(3) 0.23201(18) 0.0136(7) Uani 1 1 d . . . C9 C 0.4536(4) 0.6849(3) 0.19019(19) 0.0151(7) Uani 1 1 d . . . H9 H 0.5557 0.6622 0.1944 0.018 Uiso 1 1 calc R . . C10 C 0.4099(4) 0.7658(3) 0.14261(19) 0.0144(7) Uani 1 1 d . . . H10 H 0.4820 0.7976 0.1141 0.017 Uiso 1 1 calc R . . C11 C 0.2610(4) 0.8010(2) 0.13618(18) 0.0119(7) Uani 1 1 d . . . C12 C 0.1578(4) 0.7525(3) 0.1774(2) 0.0162(8) Uani 1 1 d . . . H12 H 0.0557 0.7752 0.1730 0.019 Uiso 1 1 calc R . . C13 C 0.2004(4) 0.6713(3) 0.22520(19) 0.0150(7) Uani 1 1 d . . . H13 H 0.1277 0.6395 0.2534 0.018 Uiso 1 1 calc R . . C14 C 0.2197(4) 0.8936(3) 0.08706(19) 0.0125(7) Uani 1 1 d . . . H14B H 0.2378 0.9565 0.1177 0.015 Uiso 1 1 calc R . . H14A H 0.2865 0.8961 0.0456 0.015 Uiso 1 1 calc R . . N15 N 0.0615(3) 0.8924(2) 0.05449(15) 0.0120(6) Uani 1 1 d . . . C16 C 0.0045(4) 0.8386(2) -0.00637(19) 0.0113(7) Uani 1 1 d . . . N17 N -0.1447(3) 0.8511(2) -0.01669(15) 0.0116(6) Uani 1 1 d . . . C18 C -0.1838(4) 0.9147(3) 0.04051(18) 0.0137(7) Uani 1 1 d . . . H18 H -0.2834 0.9367 0.0476 0.016 Uiso 1 1 calc R . . C19 C -0.0560(4) 0.9406(3) 0.08496(19) 0.0122(7) Uani 1 1 d . . . H19 H -0.0494 0.9835 0.1283 0.015 Uiso 1 1 calc R . . C20 C 0.0991(4) 0.7789(3) -0.0550(2) 0.0166(7) Uani 1 1 d . . . H20A H 0.0338 0.7366 -0.0900 0.025 Uiso 1 1 calc R . . H20B H 0.1682 0.7348 -0.0233 0.025 Uiso 1 1 calc R . . H20C H 0.1576 0.8260 -0.0837 0.025 Uiso 1 1 calc R . . O21 O 0.1687(3) 0.36688(19) 0.03462(14) 0.0207(6) Uani 1 1 d . . . S22 S 0.26652(10) 0.42375(7) -0.01617(5) 0.0195(2) Uani 1 1 d . . . C23 C 0.3153(4) 0.5414(3) 0.0313(2) 0.0249(9) Uani 1 1 d . . . H23B H 0.2234 0.5745 0.0458 0.037 Uiso 1 1 calc R . . H23C H 0.3655 0.5867 -0.0024 0.037 Uiso 1 1 calc R . . H23A H 0.3839 0.5274 0.0767 0.037 Uiso 1 1 calc R . . C24 C 0.1393(5) 0.4739(3) -0.0905(2) 0.0301(10) Uani 1 1 d . . . H24A H 0.0998 0.4178 -0.1233 0.045 Uiso 1 1 calc R . . H24B H 0.1928 0.5230 -0.1200 0.045 Uiso 1 1 calc R . . H24C H 0.0553 0.5085 -0.0691 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0086(2) 0.0148(2) 0.0122(2) -0.00194(17) -0.00044(15) -0.00182(17) Cl1 0.0096(4) 0.0318(5) 0.0166(4) -0.0059(4) 0.0012(3) 0.0007(4) N1 0.0106(15) 0.0149(15) 0.0141(15) 0.0002(12) -0.0011(11) -0.0009(12) Cl2 0.0126(4) 0.0162(4) 0.0136(4) 0.0002(3) 0.0004(3) -0.0006(3) C2 0.0130(18) 0.0134(17) 0.0135(17) 0.0002(14) 0.0006(13) -0.0020(14) N3 0.0136(15) 0.0123(15) 0.0095(14) 0.0029(11) -0.0023(11) -0.0016(12) C4 0.0103(18) 0.0177(19) 0.0180(18) 0.0039(14) -0.0031(14) -0.0031(14) C5 0.0104(18) 0.0188(19) 0.0157(18) 0.0022(14) 0.0007(14) -0.0024(14) C6 0.0144(19) 0.0194(19) 0.0204(19) -0.0040(15) 0.0043(15) -0.0046(15) C7 0.0177(19) 0.0135(18) 0.0140(18) -0.0024(13) -0.0004(14) -0.0001(14) C8 0.0162(19) 0.0144(17) 0.0090(16) -0.0054(13) -0.0049(13) -0.0007(14) C9 0.0105(18) 0.0209(19) 0.0132(17) -0.0021(14) -0.0031(13) -0.0020(14) C10 0.0134(18) 0.0137(18) 0.0163(18) -0.0023(14) 0.0029(14) -0.0016(14) C11 0.0135(18) 0.0102(17) 0.0107(16) -0.0019(13) -0.0060(13) -0.0036(13) C12 0.0138(18) 0.0154(18) 0.0193(19) -0.0016(14) 0.0011(14) 0.0006(14) C13 0.0149(19) 0.0143(18) 0.0157(18) 0.0011(14) 0.0019(14) -0.0041(14) C14 0.0106(17) 0.0120(17) 0.0143(17) -0.0001(13) -0.0023(13) 0.0006(14) N15 0.0082(14) 0.0147(15) 0.0126(14) 0.0028(11) -0.0025(11) 0.0002(12) C16 0.0107(17) 0.0094(16) 0.0142(17) 0.0028(13) 0.0023(13) 0.0007(13) N17 0.0108(15) 0.0121(14) 0.0116(14) 0.0003(11) -0.0009(11) 0.0000(11) C18 0.0156(19) 0.0146(18) 0.0107(16) 0.0008(13) 0.0005(13) 0.0012(14) C19 0.0111(18) 0.0142(17) 0.0118(17) -0.0007(13) 0.0034(13) -0.0003(14) C20 0.0110(18) 0.0182(18) 0.0203(19) -0.0027(15) 0.0002(14) 0.0002(15) O21 0.0186(14) 0.0193(14) 0.0234(14) 0.0024(11) -0.0018(11) -0.0033(11) S22 0.0164(5) 0.0214(5) 0.0205(5) -0.0001(4) 0.0002(4) -0.0003(4) C23 0.023(2) 0.025(2) 0.026(2) 0.0001(17) -0.0016(17) -0.0059(17) C24 0.028(2) 0.041(3) 0.021(2) 0.0056(18) -0.0037(17) -0.001(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 N17 1.967(3) 3_565 ? Cu1 N1 1.973(3) . ? Cu1 Cl1 2.3122(9) . ? Cu1 O21 2.368(3) . ? Cu1 Cl2 2.3723(9) . ? N1 C2 1.337(4) . ? N1 C5 1.381(4) . ? C2 N3 1.351(4) . ? C2 C6 1.492(5) . ? N3 C4 1.375(4) . ? N3 C7 1.474(4) . ? C4 C5 1.355(5) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.510(5) . ? C7 H7B 0.9900 . ? C7 H7A 0.9900 . ? C8 C13 1.387(5) . ? C8 C9 1.399(5) . ? C9 C10 1.385(5) . ? C9 H9 0.9500 . ? C10 C11 1.394(5) . ? C10 H10 0.9500 . ? C11 C12 1.381(5) . ? C11 C14 1.516(5) . ? C12 C13 1.388(5) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 N15 1.467(4) . ? C14 H14B 0.9900 . ? C14 H14A 0.9900 . ? N15 C16 1.349(4) . ? N15 C19 1.374(4) . ? C16 N17 1.330(4) . ? C16 C20 1.482(5) . ? N17 C18 1.383(4) . ? N17 Cu1 1.967(3) 3_565 ? C18 C19 1.363(5) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? O21 S22 1.507(3) . ? S22 C24 1.780(4) . ? S22 C23 1.785(4) . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C23 H23A 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 N17 Cu1 N1 164.87(12) 3_565 . ? N17 Cu1 Cl1 93.59(8) 3_565 . ? N1 Cu1 Cl1 93.43(8) . . ? N17 Cu1 O21 82.29(10) 3_565 . ? N1 Cu1 O21 82.63(11) . . ? Cl1 Cu1 O21 113.27(7) . . ? N17 Cu1 Cl2 93.56(8) 3_565 . ? N1 Cu1 Cl2 93.99(8) . . ? Cl1 Cu1 Cl2 122.30(4) . . ? O21 Cu1 Cl2 124.43(6) . . ? C2 N1 C5 105.9(3) . . ? C2 N1 Cu1 125.6(2) . . ? C5 N1 Cu1 128.2(2) . . ? N1 C2 N3 110.2(3) . . ? N1 C2 C6 126.3(3) . . ? N3 C2 C6 123.5(3) . . ? C2 N3 C4 108.0(3) . . ? C2 N3 C7 126.5(3) . . ? C4 N3 C7 125.2(3) . . ? C5 C4 N3 106.2(3) . . ? C5 C4 H4 126.9 . . ? N3 C4 H4 126.9 . . ? C4 C5 N1 109.7(3) . . ? C4 C5 H5 125.1 . . ? N1 C5 H5 125.1 . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N3 C7 C8 110.9(3) . . ? N3 C7 H7B 109.5 . . ? C8 C7 H7B 109.5 . . ? N3 C7 H7A 109.5 . . ? C8 C7 H7A 109.5 . . ? H7B C7 H7A 108.0 . . ? C13 C8 C9 118.7(3) . . ? C13 C8 C7 121.4(3) . . ? C9 C8 C7 119.9(3) . . ? C10 C9 C8 120.5(3) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 120.6(3) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 118.6(3) . . ? C12 C11 C14 122.3(3) . . ? C10 C11 C14 119.0(3) . . ? C11 C12 C13 121.2(3) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C8 C13 C12 120.3(3) . . ? C8 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? N15 C14 C11 112.9(3) . . ? N15 C14 H14B 109.0 . . ? C11 C14 H14B 109.0 . . ? N15 C14 H14A 109.0 . . ? C11 C14 H14A 109.0 . . ? H14B C14 H14A 107.8 . . ? C16 N15 C19 108.3(3) . . ? C16 N15 C14 126.5(3) . . ? C19 N15 C14 125.0(3) . . ? N17 C16 N15 109.8(3) . . ? N17 C16 C20 126.6(3) . . ? N15 C16 C20 123.5(3) . . ? C16 N17 C18 106.8(3) . . ? C16 N17 Cu1 124.7(2) . 3_565 ? C18 N17 Cu1 128.2(2) . 3_565 ? C19 C18 N17 108.8(3) . . ? C19 C18 H18 125.6 . . ? N17 C18 H18 125.6 . . ? C18 C19 N15 106.2(3) . . ? C18 C19 H19 126.9 . . ? N15 C19 H19 126.9 . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? S22 O21 Cu1 115.57(14) . . ? O21 S22 C24 105.38(17) . . ? O21 S22 C23 105.50(16) . . ? C24 S22 C23 98.2(2) . . ? S22 C23 H23B 109.5 . . ? S22 C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? S22 C23 H23A 109.5 . . ? H23B C23 H23A 109.5 . . ? H23C C23 H23A 109.5 . . ? S22 C24 H24A 109.5 . . ? S22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? S22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 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 N17 Cu1 N1 C2 57.6(6) 3_565 . . . ? Cl1 Cu1 N1 C2 175.1(3) . . . . ? O21 Cu1 N1 C2 62.0(3) . . . . ? Cl2 Cu1 N1 C2 -62.2(3) . . . . ? N17 Cu1 N1 C5 -114.4(5) 3_565 . . . ? Cl1 Cu1 N1 C5 3.1(3) . . . . ? O21 Cu1 N1 C5 -110.0(3) . . . . ? Cl2 Cu1 N1 C5 125.8(3) . . . . ? C5 N1 C2 N3 0.2(4) . . . . ? Cu1 N1 C2 N3 -173.2(2) . . . . ? C5 N1 C2 C6 179.1(3) . . . . ? Cu1 N1 C2 C6 5.6(5) . . . . ? N1 C2 N3 C4 -0.2(4) . . . . ? C6 C2 N3 C4 -179.0(3) . . . . ? N1 C2 N3 C7 173.8(3) . . . . ? C6 C2 N3 C7 -5.1(5) . . . . ? C2 N3 C4 C5 0.0(4) . . . . ? C7 N3 C4 C5 -174.0(3) . . . . ? N3 C4 C5 N1 0.1(4) . . . . ? C2 N1 C5 C4 -0.2(4) . . . . ? Cu1 N1 C5 C4 173.0(2) . . . . ? C2 N3 C7 C8 -82.4(4) . . . . ? C4 N3 C7 C8 90.6(4) . . . . ? N3 C7 C8 C13 108.0(4) . . . . ? N3 C7 C8 C9 -70.5(4) . . . . ? C13 C8 C9 C10 -0.4(5) . . . . ? C7 C8 C9 C10 178.1(3) . . . . ? C8 C9 C10 C11 0.7(5) . . . . ? C9 C10 C11 C12 -0.9(5) . . . . ? C9 C10 C11 C14 176.5(3) . . . . ? C10 C11 C12 C13 0.9(5) . . . . ? C14 C11 C12 C13 -176.4(3) . . . . ? C9 C8 C13 C12 0.3(5) . . . . ? C7 C8 C13 C12 -178.2(3) . . . . ? C11 C12 C13 C8 -0.6(5) . . . . ? C12 C11 C14 N15 -31.7(4) . . . . ? C10 C11 C14 N15 151.0(3) . . . . ? C11 C14 N15 C16 -79.7(4) . . . . ? C11 C14 N15 C19 95.0(4) . . . . ? C19 N15 C16 N17 0.7(4) . . . . ? C14 N15 C16 N17 176.1(3) . . . . ? C19 N15 C16 C20 178.2(3) . . . . ? C14 N15 C16 C20 -6.4(5) . . . . ? N15 C16 N17 C18 -0.7(4) . . . . ? C20 C16 N17 C18 -178.1(3) . . . . ? N15 C16 N17 Cu1 -175.9(2) . . . 3_565 ? C20 C16 N17 Cu1 6.7(5) . . . 3_565 ? C16 N17 C18 C19 0.4(4) . . . . ? Cu1 N17 C18 C19 175.4(2) 3_565 . . . ? N17 C18 C19 N15 0.0(4) . . . . ? C16 N15 C19 C18 -0.4(4) . . . . ? C14 N15 C19 C18 -175.9(3) . . . . ? N17 Cu1 O21 S22 -103.78(16) 3_565 . . . ? N1 Cu1 O21 S22 77.40(16) . . . . ? Cl1 Cu1 O21 S22 -13.17(17) . . . . ? Cl2 Cu1 O21 S22 167.19(11) . . . . ? Cu1 O21 S22 C24 146.49(18) . . . . ? Cu1 O21 S22 C23 -110.17(18) . . . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.733 _refine_diff_density_min -0.504 _refine_diff_density_rms 0.117 # Attachment '63.CIF' data_5 _database_code_depnum_ccdc_archive 'CCDC 635647' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 6 _chemical_melting_point ? _chemical_formula_moiety 'C32 H36 Cl4 Cu2 N8, C4 H8 O2' _chemical_formula_sum 'C36 H44 Cl4 Cu2 N8 O2' _chemical_formula_weight 889.67 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.4038(15) _cell_length_b 12.927(2) _cell_length_c 18.195(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.267(3) _cell_angle_gamma 90.00 _cell_volume 1976.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 916 _exptl_absorpt_coefficient_mu 1.390 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8400 _exptl_absorpt_correction_T_max 0.9090 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10921 _diffrn_reflns_av_R_equivalents 0.0614 _diffrn_reflns_av_sigmaI/netI 0.0874 _diffrn_reflns_limit_h_min -11 _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 24 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4464 _reflns_number_gt 3240 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _computing_publication_material X-Seed _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^)+(0.0547P)^2^+1.8950P] 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 4464 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1056 _refine_ls_R_factor_gt 0.0721 _refine_ls_wR_factor_ref 0.1414 _refine_ls_wR_factor_gt 0.1311 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.153 _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 0.25307(6) 0.18890(4) 0.38149(3) 0.01073(16) Uani 1 1 d . . . Cl1 Cl 0.01554(13) 0.11370(9) 0.40748(6) 0.0138(3) Uani 1 1 d . . . N1 N 0.3635(4) 0.1552(3) 0.4748(2) 0.0126(9) Uani 1 1 d . . . Cl2 Cl 0.42887(14) 0.12601(10) 0.30028(6) 0.0174(3) Uani 1 1 d . . . C2 C 0.5178(5) 0.1691(4) 0.4908(3) 0.0135(10) Uani 1 1 d . . . N3 N 0.5550(4) 0.1235(3) 0.5557(2) 0.0119(8) Uani 1 1 d . . . C4 C 0.4200(6) 0.0770(4) 0.5823(3) 0.0151(10) Uani 1 1 d . . . H4 H 0.4118 0.0381 0.6263 0.018 Uiso 1 1 calc R . . C5 C 0.3015(5) 0.0984(4) 0.5329(3) 0.0131(10) Uani 1 1 d . . . H5 H 0.1935 0.0780 0.5371 0.016 Uiso 1 1 calc R . . C6 C 0.6337(6) 0.2273(4) 0.4470(3) 0.0189(11) Uani 1 1 d . . . H6A H 0.5820 0.2513 0.4013 0.028 Uiso 1 1 calc R . . H6B H 0.7235 0.1823 0.4354 0.028 Uiso 1 1 calc R . . H6C H 0.6726 0.2871 0.4753 0.028 Uiso 1 1 calc R . . C7 C 0.7173(6) 0.1076(4) 0.5870(3) 0.0159(10) Uani 1 1 d . . . H7A H 0.7855 0.0798 0.5480 0.019 Uiso 1 1 calc R . . H7B H 0.7120 0.0546 0.6261 0.019 Uiso 1 1 calc R . . C8 C 0.7959(5) 0.2037(3) 0.6189(2) 0.0113(10) Uani 1 1 d . . . C9 C 0.9277(6) 0.2452(4) 0.5854(3) 0.0150(10) Uani 1 1 d . . . H9 H 0.9640 0.2150 0.5412 0.018 Uiso 1 1 calc R . . C10 C 1.0077(6) 0.3296(4) 0.6148(3) 0.0151(10) Uani 1 1 d . . . H10 H 1.0962 0.3581 0.5903 0.018 Uiso 1 1 calc R . . C11 C 0.9584(5) 0.3726(4) 0.6802(3) 0.0121(10) Uani 1 1 d . . . C12 C 0.8273(6) 0.3315(4) 0.7148(3) 0.0167(11) Uani 1 1 d . . . H12 H 0.7925 0.3613 0.7594 0.020 Uiso 1 1 calc R . . C13 C 0.7465(6) 0.2475(4) 0.6850(3) 0.0160(10) Uani 1 1 d . . . H13 H 0.6574 0.2196 0.7094 0.019 Uiso 1 1 calc R . . C14 C 1.0496(6) 0.4628(4) 0.7139(3) 0.0155(11) Uani 1 1 d . . . H14B H 1.0841 0.4445 0.7646 0.019 Uiso 1 1 calc R . . H14A H 1.1462 0.4756 0.6851 0.019 Uiso 1 1 calc R . . N15 N 0.9536(4) 0.5581(3) 0.7157(2) 0.0109(8) Uani 1 1 d . . . C16 C 0.9218(5) 0.6220(4) 0.6588(2) 0.0111(10) Uani 1 1 d . . . N17 N 0.8252(4) 0.6976(3) 0.6798(2) 0.0127(8) Uani 1 1 d . . . C18 C 0.7946(5) 0.6787(4) 0.7534(2) 0.0135(10) Uani 1 1 d . . . H18 H 0.7288 0.7199 0.7835 0.016 Uiso 1 1 calc R . . C19 C 0.8727(6) 0.5932(4) 0.7751(3) 0.0162(11) Uani 1 1 d . . . H19 H 0.8720 0.5628 0.8226 0.019 Uiso 1 1 calc R . . C20 C 0.9818(6) 0.6064(4) 0.5836(3) 0.0201(11) Uani 1 1 d . . . H20A H 0.9189 0.5525 0.5586 0.030 Uiso 1 1 calc R . . H20B H 1.0937 0.5853 0.5865 0.030 Uiso 1 1 calc R . . H20C H 0.9724 0.6713 0.5559 0.030 Uiso 1 1 calc R . . C21 C 0.5144(18) 0.5218(12) 0.6325(8) 0.031(3) Uani 0.50 1 d P A -1 H21B H 0.5841 0.5753 0.6127 0.047 Uiso 0.50 1 calc PR A -1 H21C H 0.5547 0.5003 0.6811 0.047 Uiso 0.50 1 calc PR A -1 H21A H 0.4065 0.5495 0.6368 0.047 Uiso 0.50 1 calc PR A -1 C22 C 0.5110(19) 0.4292(11) 0.5811(8) 0.037(3) Uani 0.50 1 d P A -1 H22B H 0.6210 0.4050 0.5729 0.045 Uiso 0.50 1 calc PR A -1 H22A H 0.4509 0.3719 0.6036 0.045 Uiso 0.50 1 calc PR A -1 O23 O 0.4356(12) 0.4583(8) 0.5109(5) 0.034(2) Uani 0.50 1 d P A -1 C24 C 0.5324(16) 0.4986(10) 0.4600(8) 0.028(3) Uani 0.50 1 d P A -1 O25 O 0.6751(9) 0.5134(7) 0.4700(5) 0.033(2) Uani 0.50 1 d P A -1 C26 C 0.4483(19) 0.5223(15) 0.3899(9) 0.037(4) Uani 0.50 1 d P A -1 H26B H 0.5185 0.5621 0.3582 0.055 Uiso 0.50 1 calc PR A -1 H26C H 0.3525 0.5629 0.3997 0.055 Uiso 0.50 1 calc PR A -1 H26A H 0.4179 0.4576 0.3653 0.055 Uiso 0.50 1 calc PR A -1 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 0.0091(3) 0.0113(3) 0.0117(3) 0.0015(2) -0.0007(2) 0.0010(2) Cl1 0.0113(5) 0.0154(6) 0.0146(6) -0.0004(5) 0.0012(4) -0.0007(4) N1 0.0095(19) 0.014(2) 0.014(2) 0.0007(16) 0.0002(16) 0.0033(15) Cl2 0.0171(6) 0.0186(6) 0.0167(6) 0.0013(5) 0.0036(5) 0.0046(5) C2 0.011(2) 0.015(3) 0.014(2) -0.0008(19) -0.0018(18) 0.0002(19) N3 0.013(2) 0.013(2) 0.0097(19) -0.0014(16) -0.0043(15) 0.0039(16) C4 0.020(3) 0.013(2) 0.013(2) 0.0011(19) 0.000(2) 0.002(2) C5 0.010(2) 0.012(3) 0.016(2) -0.0029(19) 0.0009(19) 0.0001(18) C6 0.011(2) 0.025(3) 0.020(3) 0.004(2) -0.004(2) -0.001(2) C7 0.017(2) 0.014(3) 0.017(3) 0.001(2) -0.005(2) 0.002(2) C8 0.014(2) 0.008(2) 0.012(2) 0.0003(18) -0.0043(18) 0.0034(18) C9 0.018(2) 0.015(3) 0.013(2) -0.001(2) -0.0002(19) 0.006(2) C10 0.017(2) 0.012(3) 0.016(2) 0.0045(19) -0.001(2) 0.0020(19) C11 0.012(2) 0.012(2) 0.012(2) 0.0000(19) -0.0049(18) 0.0030(19) C12 0.019(3) 0.020(3) 0.011(2) -0.002(2) 0.0013(19) 0.005(2) C13 0.017(3) 0.014(3) 0.017(2) -0.001(2) 0.005(2) -0.002(2) C14 0.014(2) 0.014(3) 0.018(3) 0.001(2) -0.007(2) 0.0024(19) N15 0.0092(19) 0.014(2) 0.0091(19) 0.0009(16) -0.0023(15) 0.0013(16) C16 0.009(2) 0.013(2) 0.010(2) 0.0004(19) -0.0071(18) 0.0005(18) N17 0.0102(19) 0.015(2) 0.013(2) 0.0016(17) -0.0013(15) -0.0021(16) C18 0.014(2) 0.016(3) 0.011(2) -0.0022(19) 0.0002(18) 0.003(2) C19 0.020(3) 0.023(3) 0.006(2) 0.000(2) -0.0002(19) -0.002(2) C20 0.024(3) 0.017(3) 0.019(3) 0.005(2) 0.002(2) 0.005(2) C21 0.038(9) 0.026(8) 0.029(8) 0.003(6) -0.001(6) 0.008(6) C22 0.056(10) 0.027(8) 0.028(8) 0.007(6) 0.008(7) 0.003(7) O23 0.025(5) 0.041(7) 0.035(6) 0.016(5) -0.005(5) -0.005(5) C24 0.029(8) 0.016(7) 0.037(8) -0.006(6) -0.015(6) -0.006(5) O25 0.010(4) 0.041(5) 0.047(5) -0.001(4) -0.006(4) -0.003(4) C26 0.039(9) 0.043(12) 0.029(9) 0.002(8) -0.012(7) 0.005(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N17 1.949(4) 3_666 ? Cu1 N1 1.966(4) . ? Cu1 Cl2 2.2635(13) . ? Cu1 Cl1 2.2793(13) . ? N1 C2 1.335(6) . ? N1 C5 1.398(6) . ? C2 N3 1.351(6) . ? C2 C6 1.479(7) . ? N3 C4 1.380(6) . ? N3 C7 1.480(6) . ? C4 C5 1.355(6) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.517(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.385(7) . ? C8 C13 1.400(7) . ? C9 C10 1.384(7) . ? C9 H9 0.9500 . ? C10 C11 1.384(7) . ? C10 H10 0.9500 . ? C11 C12 1.386(7) . ? C11 C14 1.518(6) . ? C12 C13 1.385(7) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 N15 1.473(6) . ? C14 H14B 0.9900 . ? C14 H14A 0.9900 . ? N15 C16 1.347(6) . ? N15 C19 1.366(6) . ? C16 N17 1.332(6) . ? C16 C20 1.482(7) . ? N17 C18 1.391(6) . ? N17 Cu1 1.949(4) 3_666 ? C18 C19 1.341(7) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.519(19) . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C21 H21A 0.9800 . ? C22 O23 1.462(16) . ? C22 H22B 0.9900 . ? C22 H22A 0.9900 . ? O23 C24 1.351(14) . ? C24 O25 1.224(15) . ? C24 C26 1.477(19) . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C26 H26A 0.9800 . ? 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 N17 Cu1 N1 143.92(16) 3_666 . ? N17 Cu1 Cl2 96.54(12) 3_666 . ? N1 Cu1 Cl2 100.47(12) . . ? N17 Cu1 Cl1 98.84(11) 3_666 . ? N1 Cu1 Cl1 97.20(12) . . ? Cl2 Cu1 Cl1 124.72(5) . . ? C2 N1 C5 106.4(4) . . ? C2 N1 Cu1 126.6(3) . . ? C5 N1 Cu1 126.4(3) . . ? N1 C2 N3 109.7(4) . . ? N1 C2 C6 126.8(4) . . ? N3 C2 C6 123.5(4) . . ? C2 N3 C4 108.7(4) . . ? C2 N3 C7 126.2(4) . . ? C4 N3 C7 124.2(4) . . ? C5 C4 N3 106.1(4) . . ? C5 C4 H4 127.0 . . ? N3 C4 H4 127.0 . . ? C4 C5 N1 109.1(4) . . ? C4 C5 H5 125.4 . . ? N1 C5 H5 125.4 . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N3 C7 C8 115.1(4) . . ? N3 C7 H7A 108.5 . . ? C8 C7 H7A 108.5 . . ? N3 C7 H7B 108.5 . . ? C8 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C9 C8 C13 118.5(4) . . ? C9 C8 C7 119.6(4) . . ? C13 C8 C7 121.7(4) . . ? C10 C9 C8 121.4(4) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 C11 119.8(5) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C12 119.5(4) . . ? C10 C11 C14 119.8(4) . . ? C12 C11 C14 120.6(4) . . ? C13 C12 C11 120.6(4) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C8 120.1(5) . . ? C12 C13 H13 120.0 . . ? C8 C13 H13 120.0 . . ? N15 C14 C11 112.3(4) . . ? N15 C14 H14B 109.1 . . ? C11 C14 H14B 109.1 . . ? N15 C14 H14A 109.1 . . ? C11 C14 H14A 109.1 . . ? H14B C14 H14A 107.9 . . ? C16 N15 C19 108.1(4) . . ? C16 N15 C14 126.5(4) . . ? C19 N15 C14 125.3(4) . . ? N17 C16 N15 109.9(4) . . ? N17 C16 C20 125.9(4) . . ? N15 C16 C20 124.1(4) . . ? C16 N17 C18 106.0(4) . . ? C16 N17 Cu1 126.0(3) . 3_666 ? C18 N17 Cu1 128.0(3) . 3_666 ? C19 C18 N17 109.1(4) . . ? C19 C18 H18 125.5 . . ? N17 C18 H18 125.5 . . ? C18 C19 N15 106.9(4) . . ? C18 C19 H19 126.5 . . ? N15 C19 H19 126.5 . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O23 C22 C21 109.6(12) . . ? O23 C22 H22B 109.7 . . ? C21 C22 H22B 109.7 . . ? O23 C22 H22A 109.7 . . ? C21 C22 H22A 109.7 . . ? H22B C22 H22A 108.2 . . ? C24 O23 C22 116.2(11) . . ? O25 C24 O23 124.1(13) . . ? O25 C24 C26 123.0(14) . . ? O23 C24 C26 112.8(12) . . ? 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 N17 Cu1 N1 C2 -72.2(5) 3_666 . . . ? Cl2 Cu1 N1 C2 44.6(4) . . . . ? Cl1 Cu1 N1 C2 172.0(4) . . . . ? N17 Cu1 N1 C5 118.0(4) 3_666 . . . ? Cl2 Cu1 N1 C5 -125.3(4) . . . . ? Cl1 Cu1 N1 C5 2.1(4) . . . . ? C5 N1 C2 N3 0.3(5) . . . . ? Cu1 N1 C2 N3 -171.2(3) . . . . ? C5 N1 C2 C6 -178.2(5) . . . . ? Cu1 N1 C2 C6 10.3(7) . . . . ? N1 C2 N3 C4 0.7(5) . . . . ? C6 C2 N3 C4 179.3(5) . . . . ? N1 C2 N3 C7 170.0(4) . . . . ? C6 C2 N3 C7 -11.5(7) . . . . ? C2 N3 C4 C5 -1.5(5) . . . . ? C7 N3 C4 C5 -171.0(4) . . . . ? N3 C4 C5 N1 1.7(5) . . . . ? C2 N1 C5 C4 -1.3(5) . . . . ? Cu1 N1 C5 C4 170.2(3) . . . . ? C2 N3 C7 C8 75.5(6) . . . . ? C4 N3 C7 C8 -116.8(5) . . . . ? N3 C7 C8 C9 -112.9(5) . . . . ? N3 C7 C8 C13 72.1(6) . . . . ? C13 C8 C9 C10 -1.6(7) . . . . ? C7 C8 C9 C10 -176.7(4) . . . . ? C8 C9 C10 C11 1.6(7) . . . . ? C9 C10 C11 C12 -1.2(7) . . . . ? C9 C10 C11 C14 177.8(4) . . . . ? C10 C11 C12 C13 0.7(7) . . . . ? C14 C11 C12 C13 -178.3(4) . . . . ? C11 C12 C13 C8 -0.6(7) . . . . ? C9 C8 C13 C12 1.0(7) . . . . ? C7 C8 C13 C12 176.1(4) . . . . ? C10 C11 C14 N15 115.1(5) . . . . ? C12 C11 C14 N15 -65.9(6) . . . . ? C11 C14 N15 C16 -78.0(6) . . . . ? C11 C14 N15 C19 97.6(5) . . . . ? C19 N15 C16 N17 0.9(5) . . . . ? C14 N15 C16 N17 177.1(4) . . . . ? C19 N15 C16 C20 -177.0(4) . . . . ? C14 N15 C16 C20 -0.7(7) . . . . ? N15 C16 N17 C18 -0.6(5) . . . . ? C20 C16 N17 C18 177.2(4) . . . . ? N15 C16 N17 Cu1 178.9(3) . . . 3_666 ? C20 C16 N17 Cu1 -3.3(7) . . . 3_666 ? C16 N17 C18 C19 0.2(5) . . . . ? Cu1 N17 C18 C19 -179.3(3) 3_666 . . . ? N17 C18 C19 N15 0.4(5) . . . . ? C16 N15 C19 C18 -0.7(5) . . . . ? C14 N15 C19 C18 -177.0(4) . . . . ? C21 C22 O23 C24 87.7(15) . . . . ? C22 O23 C24 O25 -2(2) . . . . ? C22 O23 C24 C26 177.8(11) . . . . ? _diffrn_measured_fraction_theta_max 0.908 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.942 _refine_diff_density_min -0.708 _refine_diff_density_rms 0.128 # Attachment '71.cif' data_6 _database_code_depnum_ccdc_archive 'CCDC 635648' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 7 _chemical_melting_point ? _chemical_formula_moiety 'C32 H36 Cl4 Cu2 N8, C3 H3 Cl9' _chemical_formula_sum 'C35 H39 Cl13 Cu2 N8' _chemical_formula_weight 1159.67 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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 15.700(13) _cell_length_b 21.205(18) _cell_length_c 8.132(7) _cell_angle_alpha 90.00 _cell_angle_beta 121.048(13) _cell_angle_gamma 90.00 _cell_volume 2320(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour reddish-brown _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 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 1.704 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6290 _exptl_absorpt_correction_T_max 0.7269 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4230 _diffrn_reflns_av_R_equivalents 0.1316 _diffrn_reflns_av_sigmaI/netI 0.2080 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.10 _reflns_number_total 2043 _reflns_number_gt 1016 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _computing_publication_material 'X-Seed (Barbour 2001)' _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^)+(0.0943P)^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 2043 _refine_ls_number_parameters 145 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1739 _refine_ls_R_factor_gt 0.0824 _refine_ls_wR_factor_ref 0.2169 _refine_ls_wR_factor_gt 0.1724 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.954 _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 0.23430(9) 0.0000 0.0203(5) Uani 1 2 d S . . Cl1 Cl -0.05294(18) 0.28521(13) -0.2836(4) 0.0271(7) Uani 1 1 d . . . N1 N 0.1307(6) 0.2048(4) 0.0528(12) 0.018(2) Uani 1 1 d . . . Cl2 Cl -0.0054(3) 0.0000 0.2696(8) 0.0464(13) Uani 1 2 d S . . C2 C 0.1567(7) 0.1801(5) -0.0655(15) 0.019(2) Uani 1 1 d . . . Cl3 Cl 0.1763(2) 0.06895(14) 0.3909(5) 0.0384(8) Uani 1 1 d . . . N3 N 0.2554(6) 0.1669(4) 0.0308(12) 0.021(2) Uani 1 1 d . . . Cl4 Cl 0.4638(4) -0.0686(3) 0.5665(9) 0.0361(15) Uani 0.50 1 d PD . . C4 C 0.2960(7) 0.1852(4) 0.2202(15) 0.020(2) Uani 1 1 d . . . H4 H 0.3636 0.1826 0.3208 0.024 Uiso 1 1 calc R . . Cl5 Cl 0.5970(6) 0.0000 0.4863(13) 0.038(2) Uani 0.50 2 d SPD . . C5 C 0.2171(7) 0.2080(5) 0.2304(16) 0.025(3) Uani 1 1 d . . . H5 H 0.2213 0.2238 0.3436 0.030 Uiso 1 1 calc R . . C6 C 0.0913(7) 0.1645(5) -0.2674(15) 0.023(3) Uani 1 1 d . . . H6A H 0.0219 0.1677 -0.3007 0.035 Uiso 1 1 calc R . . H6B H 0.1049 0.1214 -0.2907 0.035 Uiso 1 1 calc R . . H6C H 0.1030 0.1939 -0.3466 0.035 Uiso 1 1 calc R . . C7 C 0.3117(7) 0.1371(4) -0.0469(16) 0.021(3) Uani 1 1 d . . . H7A H 0.3819 0.1508 0.0299 0.026 Uiso 1 1 calc R . . H7B H 0.2848 0.1519 -0.1803 0.026 Uiso 1 1 calc R . . C8 C 0.3078(7) 0.0657(5) -0.0462(15) 0.022(3) Uani 1 1 d . . . C9 C 0.2529(7) 0.0322(5) 0.0154(16) 0.020(2) Uani 1 1 d . . . H9 H 0.2152 0.0544 0.0579 0.025 Uiso 1 1 calc R . . C10 C 0.3622(8) 0.0318(5) -0.1070(18) 0.029(3) Uani 1 1 d . . . H10 H 0.4001 0.0537 -0.1494 0.035 Uiso 1 1 calc R . . C11 C 0.1243(11) 0.0000 0.429(3) 0.029(4) Uani 1 2 d S . . H11 H 0.1386 0.0000 0.5638 0.035 Uiso 1 2 calc SR . . C12 C 0.4778(8) 0.0000 0.459(2) 0.021(7) Uiso 0.50 2 d SPD . . H12 H 0.4261 0.0000 0.3191 0.025 Uiso 0.50 2 calc SPR . . 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 0.0243(10) 0.0185(11) 0.0199(10) 0.000 0.0127(8) 0.000 Cl1 0.0252(14) 0.0289(17) 0.0294(16) 0.0074(12) 0.0155(12) 0.0031(11) N1 0.026(5) 0.013(5) 0.016(5) 0.002(4) 0.011(4) 0.000(4) Cl2 0.041(3) 0.040(3) 0.058(3) 0.000 0.026(2) 0.000 C2 0.024(6) 0.011(6) 0.014(6) 0.004(4) 0.005(5) 0.000(4) Cl3 0.0509(18) 0.0340(18) 0.042(2) 0.0016(15) 0.0321(16) -0.0053(14) N3 0.022(5) 0.018(5) 0.016(5) -0.003(4) 0.006(4) -0.001(4) Cl4 0.045(3) 0.031(3) 0.040(4) -0.003(3) 0.027(3) -0.007(3) C4 0.022(6) 0.009(6) 0.020(6) 0.000(5) 0.004(5) -0.002(4) Cl5 0.045(5) 0.049(6) 0.039(5) 0.000 0.036(4) 0.000 C5 0.018(5) 0.027(6) 0.018(6) -0.007(5) 0.002(5) -0.004(4) C6 0.023(5) 0.026(7) 0.018(6) -0.006(5) 0.009(5) 0.003(5) C7 0.021(5) 0.013(6) 0.029(7) 0.007(5) 0.012(5) 0.007(4) C8 0.029(6) 0.020(6) 0.017(6) 0.001(5) 0.011(5) -0.005(5) C9 0.021(5) 0.018(6) 0.024(6) -0.005(5) 0.012(5) -0.001(4) C10 0.036(6) 0.015(6) 0.050(8) 0.003(5) 0.031(6) 0.003(5) C11 0.042(9) 0.022(9) 0.037(11) 0.000 0.029(9) 0.000 _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 N1 1.970(8) . ? Cu1 N1 1.970(8) 2 ? Cu1 Cl1 2.280(3) 2 ? Cu1 Cl1 2.280(3) . ? N1 C2 1.331(13) . ? N1 C5 1.382(12) . ? Cl2 C11 1.761(16) . ? C2 N3 1.356(12) . ? C2 C6 1.456(13) . ? Cl3 C11 1.778(9) . ? N3 C4 1.384(13) . ? N3 C7 1.469(13) . ? Cl4 Cl5 1.671(7) 5_656 ? Cl4 C12 1.769(5) . ? Cl4 C12 1.789(9) 5_656 ? Cl4 Cl4 1.931(12) 2_656 ? C4 C5 1.371(14) . ? Cl5 C12 1.455(14) 5_656 ? Cl5 Cl4 1.671(7) 2_656 ? Cl5 Cl4 1.671(7) 5_656 ? Cl5 C12 1.768(5) . ? C7 C8 1.516(14) . ? C8 C10 1.389(15) . ? C8 C9 1.393(14) . ? C9 C9 1.367(19) 6 ? C10 C10 1.35(2) 6 ? C11 Cl3 1.778(9) 6 ? C12 Cl4 1.769(5) 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 N1 Cu1 N1 143.0(5) . 2 ? N1 Cu1 Cl1 97.7(3) . 2 ? N1 Cu1 Cl1 99.6(3) 2 2 ? N1 Cu1 Cl1 99.6(3) . . ? N1 Cu1 Cl1 97.7(3) 2 . ? Cl1 Cu1 Cl1 123.47(18) 2 . ? C2 N1 C5 105.8(8) . . ? C2 N1 Cu1 129.9(7) . . ? C5 N1 Cu1 124.3(7) . . ? N1 C2 N3 110.4(9) . . ? N1 C2 C6 127.1(9) . . ? N3 C2 C6 122.4(10) . . ? C2 N3 C4 108.6(9) . . ? C2 N3 C7 127.0(9) . . ? C4 N3 C7 124.4(8) . . ? Cl5 Cl4 C12 49.9(5) 5_656 . ? Cl5 Cl4 C12 61.4(3) 5_656 5_656 ? C12 Cl4 C12 21.8(9) . 5_656 ? Cl5 Cl4 Cl4 106.3(4) 5_656 2_656 ? C12 Cl4 Cl4 57.6(3) . 2_656 ? C12 Cl4 Cl4 56.6(4) 5_656 2_656 ? C5 C4 N3 104.7(8) . . ? C12 Cl5 Cl4 68.5(4) 5_656 2_656 ? C12 Cl5 Cl4 68.5(4) 5_656 5_656 ? Cl4 Cl5 Cl4 121.2(6) 2_656 5_656 ? C12 Cl5 C12 21.4(11) 5_656 . ? Cl4 Cl5 C12 62.6(3) 2_656 . ? Cl4 Cl5 C12 62.6(3) 5_656 . ? C4 C5 N1 110.5(10) . . ? N3 C7 C8 113.2(8) . . ? C10 C8 C9 118.1(10) . . ? C10 C8 C7 118.9(9) . . ? C9 C8 C7 123.0(10) . . ? C9 C9 C8 120.6(6) 6 . ? C10 C10 C8 121.2(6) 6 . ? Cl2 C11 Cl3 109.4(7) . . ? Cl2 C11 Cl3 109.4(7) . 6 ? Cl3 C11 Cl3 110.7(8) . 6 ? Cl5 C12 Cl4 109.4(5) . 6 ? Cl5 C12 Cl4 109.4(5) . . ? Cl4 C12 Cl4 110.7(8) 6 . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.814 _refine_diff_density_min -1.126 _refine_diff_density_rms 0.163 # Attachment '81.CIF' data_7 _database_code_depnum_ccdc_archive 'CCDC 635649' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 8 _chemical_melting_point ? _chemical_formula_moiety 'C40 H52 Cl4 Cu2 N8 O4, C32 H36 Cl4 Cu2 N8, C4 H8 O2' _chemical_formula_sum 'C76 H96 Cl8 Cu4 N16 O6' _chemical_formula_weight 1867.45 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6006(17) _cell_length_b 13.126(3) _cell_length_c 17.942(4) _cell_angle_alpha 87.547(4) _cell_angle_beta 87.705(4) _cell_angle_gamma 81.627(4) _cell_volume 2000.9(8) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow-brownish _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 1.379 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6745 _exptl_absorpt_correction_T_max 0.9730 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23305 _diffrn_reflns_av_R_equivalents 0.0856 _diffrn_reflns_av_sigmaI/netI 0.1251 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 28.35 _reflns_number_total 9260 _reflns_number_gt 6320 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _computing_publication_material ? _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^)+(0.0586P)^2^+2.2656P] 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 9260 _refine_ls_number_parameters 500 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.1327 _refine_ls_R_factor_gt 0.0879 _refine_ls_wR_factor_ref 0.1733 _refine_ls_wR_factor_gt 0.1568 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.18973(8) 0.29862(5) 0.35398(4) 0.01319(18) Uani 1 1 d . . . Cl1 Cl 0.40278(17) 0.33879(11) 0.41527(8) 0.0183(3) Uani 1 1 d . . . N1 N 0.2994(6) 0.1766(4) 0.3058(3) 0.0142(11) Uani 1 1 d . . . Cu2 Cu 0.76854(8) 0.79538(5) 0.11127(4) 0.01209(18) Uani 1 1 d . . . Cl2 Cl 0.10094(17) 0.39262(11) 0.24998(8) 0.0175(3) Uani 1 1 d . . . C2 C 0.3031(7) 0.1607(5) 0.2296(3) 0.0161(13) Uani 1 1 d . . . H2 H 0.2538 0.2074 0.1929 0.019 Uiso 1 1 calc R . . Cl3 Cl 0.91649(17) 0.85796(11) 0.19708(8) 0.0166(3) Uani 1 1 d . . . C3 C 0.3883(7) 0.0679(4) 0.2163(3) 0.0171(14) Uani 1 1 d . . . H3 H 0.4102 0.0377 0.1692 0.020 Uiso 1 1 calc R . . Cl4 Cl 0.52163(16) 0.87270(11) 0.08180(8) 0.0150(3) Uani 1 1 d . . . N4 N 0.4366(6) 0.0262(4) 0.2839(3) 0.0146(11) Uani 1 1 d . . . C5 C 0.3802(7) 0.0932(4) 0.3372(3) 0.0129(12) Uani 1 1 d . . . C6 C 0.4048(7) 0.0729(5) 0.4179(3) 0.0166(13) Uani 1 1 d . . . H6A H 0.4163 0.1374 0.4413 0.025 Uiso 1 1 calc R . . H6B H 0.5001 0.0232 0.4249 0.025 Uiso 1 1 calc R . . H6C H 0.3141 0.0448 0.4410 0.025 Uiso 1 1 calc R . . C7 C 0.5293(7) -0.0753(4) 0.2958(3) 0.0145(13) Uani 1 1 d U . . H7A H 0.6105 -0.0699 0.3324 0.017 Uiso 1 1 calc R . . H7B H 0.5842 -0.0966 0.2482 0.017 Uiso 1 1 calc R . . C8 C 0.4335(6) -0.1574(4) 0.3234(3) 0.0102(12) Uani 1 1 d U . . C9 C 0.3257(7) -0.1899(5) 0.2775(3) 0.0178(13) Uani 1 1 d U . . H9 H 0.3103 -0.1584 0.2292 0.021 Uiso 1 1 calc R . . C10 C 0.2401(7) -0.2678(4) 0.3013(3) 0.0154(13) Uani 1 1 d . . . H10 H 0.1659 -0.2887 0.2694 0.018 Uiso 1 1 calc R . . C11 C 0.2624(7) -0.3159(4) 0.3721(3) 0.0120(12) Uani 1 1 d . . . C12 C 0.3685(7) -0.2818(5) 0.4187(3) 0.0170(13) Uani 1 1 d . . . H12 H 0.3837 -0.3124 0.4673 0.020 Uiso 1 1 calc R . . C13 C 0.4517(7) -0.2035(4) 0.3941(3) 0.0135(12) Uani 1 1 d . . . H13 H 0.5233 -0.1808 0.4265 0.016 Uiso 1 1 calc R . . C14 C 0.1745(7) -0.4040(4) 0.3955(3) 0.0143(13) Uani 1 1 d . . . H14A H 0.0834 -0.4023 0.3632 0.017 Uiso 1 1 calc R . . H14B H 0.2444 -0.4699 0.3879 0.017 Uiso 1 1 calc R . . N15 N 0.1180(6) -0.4002(4) 0.4743(3) 0.0124(10) Uani 1 1 d . . . C16 C 0.1892(7) -0.4586(4) 0.5320(3) 0.0142(13) Uani 1 1 d . . . H16 H 0.2828 -0.5068 0.5288 0.017 Uiso 1 1 calc R . . C17 C 0.1007(7) -0.4344(4) 0.5941(3) 0.0147(13) Uani 1 1 d . . . H17 H 0.1217 -0.4632 0.6428 0.018 Uiso 1 1 calc R . . N18 N -0.0255(6) -0.3611(3) 0.5759(3) 0.0131(11) Uani 1 1 d . . . C19 C -0.0124(7) -0.3422(5) 0.5020(3) 0.0148(13) Uani 1 1 d . . . C20 C -0.1190(7) -0.2691(5) 0.4557(3) 0.0194(14) Uani 1 1 d . . . H20A H -0.2076 -0.3025 0.4414 0.029 Uiso 1 1 calc R . . H20B H -0.0615 -0.2483 0.4106 0.029 Uiso 1 1 calc R . . H20C H -0.1586 -0.2082 0.4842 0.029 Uiso 1 1 calc R . . O21 O -0.0555(5) 0.1671(3) 0.3383(2) 0.0229(10) Uani 1 1 d . . . C22 C -0.0351(8) 0.0653(5) 0.3096(4) 0.0230(15) Uani 1 1 d . . . H22A H 0.0640 0.0542 0.2791 0.028 Uiso 1 1 calc R . . H22B H -0.1229 0.0591 0.2769 0.028 Uiso 1 1 calc R . . C23 C -0.0300(8) -0.0149(5) 0.3710(4) 0.0235(15) Uani 1 1 d . . . H23A H -0.0212 -0.0836 0.3492 0.028 Uiso 1 1 calc R . . H23B H 0.0646 -0.0134 0.4003 0.028 Uiso 1 1 calc R . . O24 O -0.1665(5) -0.0001(3) 0.4195(2) 0.0251(11) Uani 1 1 d . . . C25 C -0.1860(8) 0.1024(5) 0.4466(4) 0.0244(15) Uani 1 1 d . . . H25A H -0.0955 0.1104 0.4772 0.029 Uiso 1 1 calc R . . H25B H -0.2826 0.1138 0.4789 0.029 Uiso 1 1 calc R . . C26 C -0.1976(8) 0.1809(5) 0.3833(4) 0.0216(14) Uani 1 1 d . . . H26A H -0.2880 0.1732 0.3526 0.026 Uiso 1 1 calc R . . H26B H -0.2148 0.2511 0.4031 0.026 Uiso 1 1 calc R . . N27 N 0.6995(6) 0.6865(4) 0.1773(3) 0.0114(10) Uani 1 1 d . . . C28 C 0.7247(7) 0.6716(5) 0.2528(3) 0.0173(13) Uani 1 1 d . . . H28 H 0.7877 0.7088 0.2807 0.021 Uiso 1 1 calc R . . C29 C 0.6461(7) 0.5964(4) 0.2805(3) 0.0161(13) Uani 1 1 d . . . H29 H 0.6436 0.5705 0.3307 0.019 Uiso 1 1 calc R . . N30 N 0.5701(6) 0.5643(4) 0.2219(3) 0.0166(11) Uani 1 1 d . . . C31 C 0.6042(7) 0.6197(5) 0.1606(3) 0.0141(13) Uani 1 1 d . . . C32 C 0.5468(8) 0.6057(5) 0.0849(4) 0.0241(15) Uani 1 1 d . . . H32A H 0.4315 0.6167 0.0864 0.036 Uiso 1 1 calc R . . H32B H 0.5852 0.5356 0.0693 0.036 Uiso 1 1 calc R . . H32C H 0.5858 0.6556 0.0493 0.036 Uiso 1 1 calc R . . C33 C 0.4726(7) 0.4803(5) 0.2253(4) 0.0205(14) Uani 1 1 d . . . H33A H 0.3719 0.5047 0.2010 0.025 Uiso 1 1 calc R . . H33B H 0.4484 0.4622 0.2782 0.025 Uiso 1 1 calc R . . C34 C 0.5537(7) 0.3858(5) 0.1875(3) 0.0178(14) Uani 1 1 d . . . C35 C 0.7042(7) 0.3415(4) 0.2070(3) 0.0179(13) Uani 1 1 d . . . H35 H 0.7582 0.3722 0.2433 0.021 Uiso 1 1 calc R . . C36 C 0.7756(7) 0.2525(4) 0.1734(3) 0.0161(13) Uani 1 1 d . . . H36 H 0.8782 0.2224 0.1872 0.019 Uiso 1 1 calc R . . C37 C 0.6995(7) 0.2072(4) 0.1204(3) 0.0128(12) Uani 1 1 d . . . C38 C 0.5522(7) 0.2519(5) 0.0996(3) 0.0158(13) Uani 1 1 d . . . H38 H 0.5002 0.2219 0.0622 0.019 Uiso 1 1 calc R . . C39 C 0.4788(7) 0.3410(5) 0.1329(3) 0.0186(14) Uani 1 1 d . . . H39 H 0.3770 0.3714 0.1183 0.022 Uiso 1 1 calc R . . C40 C 0.7745(7) 0.1075(4) 0.0853(3) 0.0160(13) Uani 1 1 d . . . H40A H 0.7801 0.0508 0.1237 0.019 Uiso 1 1 calc R . . H40B H 0.7067 0.0910 0.0455 0.019 Uiso 1 1 calc R . . N41 N 0.9342(5) 0.1128(4) 0.0531(3) 0.0130(11) Uani 1 1 d . . . C42 C 0.9677(7) 0.1665(4) -0.0092(3) 0.0134(12) Uani 1 1 d . . . N43 N 1.1235(6) 0.1541(4) -0.0226(3) 0.0123(10) Uani 1 1 d . . . C44 C 1.1879(7) 0.0894(4) 0.0342(3) 0.0141(13) Uani 1 1 d . . . H44 H 1.2970 0.0663 0.0394 0.017 Uiso 1 1 calc R . . C45 C 1.0736(7) 0.0643(4) 0.0808(3) 0.0151(13) Uani 1 1 d . . . H45 H 1.0862 0.0211 0.1246 0.018 Uiso 1 1 calc R . . C46 C 0.8464(7) 0.2300(5) -0.0549(4) 0.0206(14) Uani 1 1 d . . . H46A H 0.8979 0.2643 -0.0966 0.031 Uiso 1 1 calc R . . H46B H 0.7848 0.2821 -0.0239 0.031 Uiso 1 1 calc R . . H46C H 0.7765 0.1856 -0.0744 0.031 Uiso 1 1 calc R . . O47 O 0.9235(6) 0.5932(4) 0.0303(3) 0.0399(12) Uani 1 1 d U . . C48 C 0.9803(11) 0.5869(7) -0.0465(5) 0.0509(16) Uani 1 1 d U . . H48A H 0.9084 0.6350 -0.0778 0.061 Uiso 1 1 calc R . . H48B H 1.0850 0.6100 -0.0506 0.061 Uiso 1 1 calc R . . C49 C 1.0071(11) 0.5123(7) 0.0750(5) 0.0523(16) Uani 1 1 d U . . H49A H 1.1144 0.5286 0.0816 0.063 Uiso 1 1 calc R . . H49B H 0.9542 0.5112 0.1250 0.063 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0151(4) 0.0128(4) 0.0104(4) -0.0041(3) 0.0018(3) 0.0029(3) Cl1 0.0175(8) 0.0173(8) 0.0192(8) -0.0065(6) -0.0021(6) 0.0020(6) N1 0.020(3) 0.012(3) 0.010(2) -0.004(2) 0.007(2) 0.001(2) Cu2 0.0121(4) 0.0135(4) 0.0105(4) -0.0004(3) 0.0005(3) -0.0013(3) Cl2 0.0188(8) 0.0187(8) 0.0136(7) 0.0013(6) 0.0006(6) 0.0012(6) C2 0.024(3) 0.015(3) 0.009(3) -0.003(2) 0.005(2) -0.002(3) Cl3 0.0166(7) 0.0185(8) 0.0153(7) -0.0026(6) -0.0022(6) -0.0041(6) C3 0.027(4) 0.013(3) 0.010(3) -0.002(2) 0.008(3) 0.000(3) Cl4 0.0130(7) 0.0163(7) 0.0151(7) -0.0022(6) 0.0007(6) 0.0004(6) N4 0.015(3) 0.016(3) 0.012(3) -0.004(2) 0.003(2) 0.000(2) C5 0.010(3) 0.014(3) 0.016(3) -0.003(2) 0.005(2) -0.008(2) C6 0.018(3) 0.015(3) 0.016(3) -0.003(3) -0.001(3) 0.000(3) C7 0.0141(15) 0.0143(15) 0.0148(15) -0.0015(9) 0.0005(9) -0.0015(9) C8 0.0101(14) 0.0099(14) 0.0104(14) -0.0011(9) -0.0002(9) -0.0003(9) C9 0.0183(16) 0.0177(16) 0.0172(16) -0.0001(10) -0.0001(10) -0.0017(10) C10 0.013(3) 0.013(3) 0.019(3) -0.006(3) -0.004(2) 0.003(2) C11 0.012(3) 0.008(3) 0.015(3) -0.004(2) 0.005(2) 0.003(2) C12 0.023(3) 0.013(3) 0.013(3) -0.001(2) -0.002(3) 0.003(3) C13 0.015(3) 0.009(3) 0.016(3) -0.008(2) -0.004(2) 0.003(2) C14 0.014(3) 0.014(3) 0.015(3) -0.005(2) 0.003(2) -0.002(2) N15 0.018(3) 0.011(3) 0.008(2) 0.000(2) 0.002(2) -0.001(2) C16 0.007(3) 0.013(3) 0.023(3) -0.002(3) 0.002(2) -0.003(2) C17 0.016(3) 0.012(3) 0.016(3) 0.001(2) -0.004(2) 0.000(2) N18 0.016(3) 0.007(2) 0.015(3) -0.002(2) 0.000(2) 0.000(2) C19 0.012(3) 0.015(3) 0.019(3) -0.004(3) -0.003(2) -0.004(2) C20 0.025(4) 0.017(3) 0.016(3) 0.001(3) 0.000(3) -0.003(3) O21 0.024(2) 0.018(2) 0.027(3) -0.003(2) 0.009(2) -0.006(2) C22 0.031(4) 0.018(3) 0.019(3) -0.006(3) 0.012(3) -0.002(3) C23 0.033(4) 0.018(3) 0.018(3) -0.001(3) 0.001(3) 0.000(3) O24 0.033(3) 0.020(2) 0.023(2) -0.001(2) 0.011(2) -0.010(2) C25 0.033(4) 0.021(4) 0.020(3) -0.008(3) 0.009(3) -0.008(3) C26 0.024(4) 0.014(3) 0.027(4) -0.008(3) 0.003(3) -0.003(3) N27 0.016(3) 0.009(2) 0.009(2) -0.0012(19) 0.001(2) -0.002(2) C28 0.015(3) 0.021(3) 0.014(3) -0.002(3) -0.003(2) 0.005(3) C29 0.023(3) 0.010(3) 0.013(3) 0.000(2) 0.000(3) 0.004(3) N30 0.022(3) 0.012(3) 0.014(3) 0.000(2) 0.005(2) 0.000(2) C31 0.017(3) 0.015(3) 0.009(3) -0.002(2) -0.002(2) 0.001(2) C32 0.038(4) 0.013(3) 0.024(4) -0.002(3) -0.010(3) -0.007(3) C33 0.020(3) 0.014(3) 0.026(4) -0.004(3) 0.011(3) 0.001(3) C34 0.018(3) 0.019(3) 0.017(3) 0.001(3) 0.009(3) -0.007(3) C35 0.026(4) 0.012(3) 0.016(3) -0.004(3) -0.002(3) -0.004(3) C36 0.021(3) 0.010(3) 0.016(3) 0.000(2) -0.004(3) 0.001(2) C37 0.015(3) 0.010(3) 0.014(3) -0.002(2) 0.006(2) -0.004(2) C38 0.015(3) 0.018(3) 0.016(3) -0.001(3) 0.002(2) -0.010(3) C39 0.016(3) 0.018(3) 0.020(3) 0.001(3) 0.001(3) 0.000(3) C40 0.018(3) 0.014(3) 0.018(3) -0.008(3) 0.009(3) -0.005(3) N41 0.010(2) 0.015(3) 0.014(3) -0.003(2) 0.003(2) -0.002(2) C42 0.015(3) 0.015(3) 0.011(3) -0.008(2) 0.003(2) -0.001(2) N43 0.017(3) 0.010(2) 0.012(2) -0.001(2) 0.000(2) -0.006(2) C44 0.013(3) 0.017(3) 0.014(3) -0.006(2) -0.004(2) -0.002(2) C45 0.023(3) 0.012(3) 0.010(3) -0.005(2) 0.001(2) -0.002(3) C46 0.010(3) 0.028(4) 0.023(3) 0.001(3) 0.005(3) -0.002(3) O47 0.0397(14) 0.0398(14) 0.0404(14) -0.0013(9) -0.0022(9) -0.0062(9) C48 0.0525(19) 0.0510(19) 0.0488(16) -0.0013(10) -0.0010(10) -0.0068(10) C49 0.0534(19) 0.0515(18) 0.0511(17) 0.0005(10) -0.0026(10) -0.0051(10) _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 N1 1.954(5) . ? Cu1 N18 1.965(5) 2_556 ? Cu1 Cl2 2.2870(16) . ? Cu1 Cl1 2.3102(17) . ? N1 C5 1.325(7) . ? N1 C2 1.390(7) . ? Cu2 N43 1.951(5) 2_765 ? Cu2 N27 1.961(5) . ? Cu2 Cl3 2.2878(16) . ? Cu2 Cl4 2.2881(16) . ? C2 C3 1.352(8) . ? C2 H2 0.9500 . ? C3 N4 1.363(7) . ? C3 H3 0.9500 . ? N4 C5 1.355(7) . ? N4 C7 1.462(7) . ? C5 C6 1.478(8) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.506(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C13 1.386(8) . ? C8 C9 1.388(8) . ? C9 C10 1.388(8) . ? C9 H9 0.9500 . ? C10 C11 1.402(8) . ? C10 H10 0.9500 . ? C11 C12 1.394(8) . ? C11 C14 1.508(8) . ? C12 C13 1.383(8) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 N15 1.478(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? N15 C19 1.350(7) . ? N15 C16 1.372(7) . ? C16 C17 1.347(8) . ? C16 H16 0.9500 . ? C17 N18 1.382(7) . ? C17 H17 0.9500 . ? N18 C19 1.341(7) . ? N18 Cu1 1.965(5) 2_556 ? C19 C20 1.480(8) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? O21 C26 1.430(7) . ? O21 C22 1.437(7) . ? C22 C23 1.489(9) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 O24 1.429(7) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? O24 C25 1.434(7) . ? C25 C26 1.498(9) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? N27 C31 1.336(7) . ? N27 C28 1.381(7) . ? C28 C29 1.344(8) . ? C28 H28 0.9500 . ? C29 N30 1.373(7) . ? C29 H29 0.9500 . ? N30 C31 1.338(7) . ? N30 C33 1.477(8) . ? C31 C32 1.490(8) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 C34 1.506(8) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C39 1.389(8) . ? C34 C35 1.391(9) . ? C35 C36 1.388(8) . ? C35 H35 0.9500 . ? C36 C37 1.379(8) . ? C36 H36 0.9500 . ? C37 C38 1.375(8) . ? C37 C40 1.522(8) . ? C38 C39 1.393(8) . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? C40 N41 1.479(7) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? N41 C42 1.339(7) . ? N41 C45 1.375(7) . ? C42 N43 1.339(7) . ? C42 C46 1.488(8) . ? N43 C44 1.379(7) . ? N43 Cu2 1.951(5) 2_765 ? C44 C45 1.334(8) . ? C44 H44 0.9500 . ? C45 H45 0.9500 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? O47 C49 1.428(9) . ? O47 C48 1.445(10) . ? C48 C49 1.408(12) 2_765 ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C49 C48 1.408(12) 2_765 ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? 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 Cu1 N18 149.7(2) . 2_556 ? N1 Cu1 Cl2 98.97(15) . . ? N18 Cu1 Cl2 96.84(15) 2_556 . ? N1 Cu1 Cl1 96.87(16) . . ? N18 Cu1 Cl1 97.13(15) 2_556 . ? Cl2 Cu1 Cl1 120.54(6) . . ? C5 N1 C2 106.6(5) . . ? C5 N1 Cu1 128.4(4) . . ? C2 N1 Cu1 125.0(4) . . ? N43 Cu2 N27 153.49(19) 2_765 . ? N43 Cu2 Cl3 96.75(14) 2_765 . ? N27 Cu2 Cl3 96.01(14) . . ? N43 Cu2 Cl4 96.36(15) 2_765 . ? N27 Cu2 Cl4 95.97(15) . . ? Cl3 Cu2 Cl4 123.09(6) . . ? C3 C2 N1 108.9(5) . . ? C3 C2 H2 125.6 . . ? N1 C2 H2 125.6 . . ? C2 C3 N4 106.5(5) . . ? C2 C3 H3 126.7 . . ? N4 C3 H3 126.7 . . ? C5 N4 C3 108.5(5) . . ? C5 N4 C7 126.5(5) . . ? C3 N4 C7 125.0(5) . . ? N1 C5 N4 109.5(5) . . ? N1 C5 C6 126.5(5) . . ? N4 C5 C6 123.9(5) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N4 C7 C8 113.8(5) . . ? N4 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? N4 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C13 C8 C9 118.4(5) . . ? C13 C8 C7 121.5(5) . . ? C9 C8 C7 120.1(5) . . ? C10 C9 C8 120.9(6) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 120.3(6) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 118.7(5) . . ? C12 C11 C14 121.7(5) . . ? C10 C11 C14 119.6(5) . . ? C13 C12 C11 120.0(5) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C8 121.7(5) . . ? C12 C13 H13 119.2 . . ? C8 C13 H13 119.2 . . ? N15 C14 C11 112.7(5) . . ? N15 C14 H14A 109.1 . . ? C11 C14 H14A 109.1 . . ? N15 C14 H14B 109.1 . . ? C11 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? C19 N15 C16 108.3(5) . . ? C19 N15 C14 126.9(5) . . ? C16 N15 C14 124.8(5) . . ? C17 C16 N15 106.7(5) . . ? C17 C16 H16 126.7 . . ? N15 C16 H16 126.7 . . ? C16 C17 N18 109.2(5) . . ? C16 C17 H17 125.4 . . ? N18 C17 H17 125.4 . . ? C19 N18 C17 106.5(5) . . ? C19 N18 Cu1 127.8(4) . 2_556 ? C17 N18 Cu1 125.7(4) . 2_556 ? N18 C19 N15 109.3(5) . . ? N18 C19 C20 127.3(5) . . ? N15 C19 C20 123.4(5) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C26 O21 C22 108.5(5) . . ? O21 C22 C23 111.3(5) . . ? O21 C22 H22A 109.4 . . ? C23 C22 H22A 109.4 . . ? O21 C22 H22B 109.4 . . ? C23 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? O24 C23 C22 112.2(5) . . ? O24 C23 H23A 109.2 . . ? C22 C23 H23A 109.2 . . ? O24 C23 H23B 109.2 . . ? C22 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C23 O24 C25 109.2(5) . . ? O24 C25 C26 110.9(5) . . ? O24 C25 H25A 109.5 . . ? C26 C25 H25A 109.5 . . ? O24 C25 H25B 109.5 . . ? C26 C25 H25B 109.5 . . ? H25A C25 H25B 108.0 . . ? O21 C26 C25 109.5(5) . . ? O21 C26 H26A 109.8 . . ? C25 C26 H26A 109.8 . . ? O21 C26 H26B 109.8 . . ? C25 C26 H26B 109.8 . . ? H26A C26 H26B 108.2 . . ? C31 N27 C28 106.1(5) . . ? C31 N27 Cu2 126.9(4) . . ? C28 N27 Cu2 126.5(4) . . ? C29 C28 N27 109.3(5) . . ? C29 C28 H28 125.3 . . ? N27 C28 H28 125.3 . . ? C28 C29 N30 106.4(5) . . ? C28 C29 H29 126.8 . . ? N30 C29 H29 126.8 . . ? C31 N30 C29 108.3(5) . . ? C31 N30 C33 125.9(5) . . ? C29 N30 C33 125.8(5) . . ? N27 C31 N30 109.8(5) . . ? N27 C31 C32 125.7(5) . . ? N30 C31 C32 124.4(6) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N30 C33 C34 112.0(5) . . ? N30 C33 H33A 109.2 . . ? C34 C33 H33A 109.2 . . ? N30 C33 H33B 109.2 . . ? C34 C33 H33B 109.2 . . ? H33A C33 H33B 107.9 . . ? C39 C34 C35 119.0(6) . . ? C39 C34 C33 120.4(6) . . ? C35 C34 C33 120.6(6) . . ? C36 C35 C34 120.0(6) . . ? C36 C35 H35 120.0 . . ? C34 C35 H35 120.0 . . ? C37 C36 C35 120.8(6) . . ? C37 C36 H36 119.6 . . ? C35 C36 H36 119.6 . . ? C38 C37 C36 119.4(5) . . ? C38 C37 C40 119.4(5) . . ? C36 C37 C40 121.2(5) . . ? C37 C38 C39 120.4(6) . . ? C37 C38 H38 119.8 . . ? C39 C38 H38 119.8 . . ? C34 C39 C38 120.3(6) . . ? C34 C39 H39 119.8 . . ? C38 C39 H39 119.8 . . ? N41 C40 C37 113.1(5) . . ? N41 C40 H40A 109.0 . . ? C37 C40 H40A 109.0 . . ? N41 C40 H40B 109.0 . . ? C37 C40 H40B 109.0 . . ? H40A C40 H40B 107.8 . . ? C42 N41 C45 107.9(5) . . ? C42 N41 C40 125.4(5) . . ? C45 N41 C40 126.8(5) . . ? N41 C42 N43 109.8(5) . . ? N41 C42 C46 123.6(5) . . ? N43 C42 C46 126.5(5) . . ? C42 N43 C44 106.0(5) . . ? C42 N43 Cu2 126.0(4) . 2_765 ? C44 N43 Cu2 127.6(4) . 2_765 ? C45 C44 N43 109.5(5) . . ? C45 C44 H44 125.2 . . ? N43 C44 H44 125.2 . . ? C44 C45 N41 106.8(5) . . ? C44 C45 H45 126.6 . . ? N41 C45 H45 126.6 . . ? C42 C46 H46A 109.5 . . ? C42 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C42 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C49 O47 C48 110.3(6) . . ? C49 C48 O47 114.2(8) 2_765 . ? C49 C48 H48A 108.7 2_765 . ? O47 C48 H48A 108.7 . . ? C49 C48 H48B 108.7 2_765 . ? O47 C48 H48B 108.7 . . ? H48A C48 H48B 107.6 . . ? C48 C49 O47 115.5(8) 2_765 . ? C48 C49 H49A 108.4 2_765 . ? O47 C49 H49A 108.4 . . ? C48 C49 H49B 108.4 2_765 . ? O47 C49 H49B 108.4 . . ? H49A C49 H49B 107.5 . . ? 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 N18 Cu1 N1 C5 -61.1(7) 2_556 . . . ? Cl2 Cu1 N1 C5 178.3(5) . . . . ? Cl1 Cu1 N1 C5 55.8(5) . . . . ? N18 Cu1 N1 C2 117.2(5) 2_556 . . . ? Cl2 Cu1 N1 C2 -3.3(5) . . . . ? Cl1 Cu1 N1 C2 -125.8(5) . . . . ? C5 N1 C2 C3 -0.7(7) . . . . ? Cu1 N1 C2 C3 -179.4(4) . . . . ? N1 C2 C3 N4 0.3(7) . . . . ? C2 C3 N4 C5 0.3(7) . . . . ? C2 C3 N4 C7 178.5(5) . . . . ? C2 N1 C5 N4 0.9(6) . . . . ? Cu1 N1 C5 N4 179.5(4) . . . . ? C2 N1 C5 C6 -177.9(6) . . . . ? Cu1 N1 C5 C6 0.7(9) . . . . ? C3 N4 C5 N1 -0.8(7) . . . . ? C7 N4 C5 N1 -178.9(5) . . . . ? C3 N4 C5 C6 178.1(5) . . . . ? C7 N4 C5 C6 0.0(9) . . . . ? C5 N4 C7 C8 77.6(7) . . . . ? C3 N4 C7 C8 -100.3(6) . . . . ? N4 C7 C8 C13 -113.8(6) . . . . ? N4 C7 C8 C9 67.3(7) . . . . ? C13 C8 C9 C10 -1.0(8) . . . . ? C7 C8 C9 C10 177.9(5) . . . . ? C8 C9 C10 C11 -0.6(9) . . . . ? C9 C10 C11 C12 1.8(8) . . . . ? C9 C10 C11 C14 -176.9(5) . . . . ? C10 C11 C12 C13 -1.3(8) . . . . ? C14 C11 C12 C13 177.4(5) . . . . ? C11 C12 C13 C8 -0.4(9) . . . . ? C9 C8 C13 C12 1.6(8) . . . . ? C7 C8 C13 C12 -177.4(5) . . . . ? C12 C11 C14 N15 41.2(7) . . . . ? C10 C11 C14 N15 -140.1(5) . . . . ? C11 C14 N15 C19 81.0(7) . . . . ? C11 C14 N15 C16 -100.9(6) . . . . ? C19 N15 C16 C17 -0.3(6) . . . . ? C14 N15 C16 C17 -178.7(5) . . . . ? N15 C16 C17 N18 -0.1(6) . . . . ? C16 C17 N18 C19 0.5(6) . . . . ? C16 C17 N18 Cu1 -179.5(4) . . . 2_556 ? C17 N18 C19 N15 -0.7(6) . . . . ? Cu1 N18 C19 N15 179.3(4) 2_556 . . . ? C17 N18 C19 C20 -179.8(6) . . . . ? Cu1 N18 C19 C20 0.2(9) 2_556 . . . ? C16 N15 C19 N18 0.7(6) . . . . ? C14 N15 C19 N18 179.0(5) . . . . ? C16 N15 C19 C20 179.8(5) . . . . ? C14 N15 C19 C20 -1.8(9) . . . . ? C26 O21 C22 C23 -58.0(7) . . . . ? O21 C22 C23 O24 56.0(7) . . . . ? C22 C23 O24 C25 -54.5(7) . . . . ? C23 O24 C25 C26 57.2(7) . . . . ? C22 O21 C26 C25 60.3(6) . . . . ? O24 C25 C26 O21 -61.4(7) . . . . ? N43 Cu2 N27 C31 -62.5(7) 2_765 . . . ? Cl3 Cu2 N27 C31 179.1(5) . . . . ? Cl4 Cu2 N27 C31 54.8(5) . . . . ? N43 Cu2 N27 C28 125.8(5) 2_765 . . . ? Cl3 Cu2 N27 C28 7.4(5) . . . . ? Cl4 Cu2 N27 C28 -116.9(5) . . . . ? C31 N27 C28 C29 0.4(6) . . . . ? Cu2 N27 C28 C29 173.5(4) . . . . ? N27 C28 C29 N30 -0.4(6) . . . . ? C28 C29 N30 C31 0.3(6) . . . . ? C28 C29 N30 C33 178.0(5) . . . . ? C28 N27 C31 N30 -0.2(6) . . . . ? Cu2 N27 C31 N30 -173.3(4) . . . . ? C28 N27 C31 C32 -178.7(6) . . . . ? Cu2 N27 C31 C32 8.3(9) . . . . ? C29 N30 C31 N27 0.0(6) . . . . ? C33 N30 C31 N27 -177.8(5) . . . . ? C29 N30 C31 C32 178.4(6) . . . . ? C33 N30 C31 C32 0.7(9) . . . . ? C31 N30 C33 C34 70.2(8) . . . . ? C29 N30 C33 C34 -107.1(7) . . . . ? N30 C33 C34 C39 -127.1(6) . . . . ? N30 C33 C34 C35 53.3(8) . . . . ? C39 C34 C35 C36 -1.7(9) . . . . ? C33 C34 C35 C36 177.9(5) . . . . ? C34 C35 C36 C37 0.4(9) . . . . ? C35 C36 C37 C38 1.2(9) . . . . ? C35 C36 C37 C40 -177.8(5) . . . . ? C36 C37 C38 C39 -1.4(9) . . . . ? C40 C37 C38 C39 177.6(5) . . . . ? C35 C34 C39 C38 1.4(9) . . . . ? C33 C34 C39 C38 -178.2(5) . . . . ? C37 C38 C39 C34 0.1(9) . . . . ? C38 C37 C40 N41 127.6(6) . . . . ? C36 C37 C40 N41 -53.4(7) . . . . ? C37 C40 N41 C42 -71.8(7) . . . . ? C37 C40 N41 C45 108.4(6) . . . . ? C45 N41 C42 N43 0.1(6) . . . . ? C40 N41 C42 N43 -179.7(5) . . . . ? C45 N41 C42 C46 -179.6(5) . . . . ? C40 N41 C42 C46 0.5(9) . . . . ? N41 C42 N43 C44 0.1(6) . . . . ? C46 C42 N43 C44 179.9(6) . . . . ? N41 C42 N43 Cu2 173.6(4) . . . 2_765 ? C46 C42 N43 Cu2 -6.7(8) . . . 2_765 ? C42 N43 C44 C45 -0.4(6) . . . . ? Cu2 N43 C44 C45 -173.7(4) 2_765 . . . ? N43 C44 C45 N41 0.5(6) . . . . ? C42 N41 C45 C44 -0.4(6) . . . . ? C40 N41 C45 C44 179.4(5) . . . . ? C49 O47 C48 C49 48.0(11) . . . 2_765 ? C48 O47 C49 C48 -48.7(11) . . . 2_765 ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.534 _refine_diff_density_min -0.938 _refine_diff_density_rms 0.145 data_I _database_code_depnum_ccdc_archive 'CCDC 635650' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 9 _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 Cl2 Cu N4, C2 H4 Cl2' _chemical_formula_sum 'C18 H22 Cl4 Cu N4' _chemical_formula_weight 499.74 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' 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.539(5) _cell_length_b 10.673(6) _cell_length_c 13.386(7) _cell_angle_alpha 104.272(10) _cell_angle_beta 91.858(10) _cell_angle_gamma 112.793(9) _cell_volume 1078.7(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 510 _exptl_absorpt_coefficient_mu 1.519 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7120 _exptl_absorpt_correction_T_max 0.8155 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6815 _diffrn_reflns_av_R_equivalents 0.0517 _diffrn_reflns_av_sigmaI/netI 0.1374 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 28.29 _reflns_number_total 4785 _reflns_number_gt 2940 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour 2001)' _computing_publication_material X-Seed _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^)+(0.0684P)^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 4785 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1259 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.1655 _refine_ls_wR_factor_gt 0.1420 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.959 _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 0.21831(9) 0.49966(7) 0.23990(6) 0.0156(2) Uani 1 1 d . . . Cl1 Cl -0.02110(18) 0.51191(16) 0.17681(12) 0.0233(4) Uani 1 1 d . . . N1 N 0.1649(6) 0.4568(5) 0.3722(4) 0.0156(10) Uani 1 1 d . . . Cl2 Cl 0.46687(18) 0.69327(15) 0.30023(12) 0.0228(4) Uani 1 1 d . . . C2 C 0.0276(7) 0.3532(6) 0.3888(4) 0.0165(12) Uani 1 1 d . . . Cl3 Cl -0.1139(2) -0.0612(2) -0.16647(17) 0.0482(5) Uani 1 1 d . . . N3 N 0.0444(6) 0.3537(5) 0.4890(4) 0.0169(11) Uani 1 1 d . . . Cl4 Cl -0.4155(3) -0.1309(2) -0.36793(15) 0.0536(6) Uani 1 1 d . . . C4 C 0.1988(7) 0.4605(6) 0.5391(5) 0.0214(14) Uani 1 1 d . . . H4 H 0.2438 0.4855 0.6104 0.026 Uiso 1 1 calc R . . C5 C 0.2735(8) 0.5228(6) 0.4665(5) 0.0196(13) Uani 1 1 d . . . H5 H 0.3829 0.5996 0.4782 0.023 Uiso 1 1 calc R . . C6 C -0.1202(7) 0.2493(6) 0.3097(5) 0.0213(14) Uani 1 1 d . . . H6A H -0.1144 0.2791 0.2458 0.032 Uiso 1 1 calc R . . H6B H -0.2274 0.2441 0.3363 0.032 Uiso 1 1 calc R . . H6C H -0.1165 0.1559 0.2945 0.032 Uiso 1 1 calc R . . C7 C -0.0747(7) 0.2494(6) 0.5362(5) 0.0188(13) Uani 1 1 d . . . H7A H -0.1944 0.2222 0.5057 0.023 Uiso 1 1 calc R . . H7B H -0.0628 0.2924 0.6121 0.023 Uiso 1 1 calc R . . C8 C -0.0368(7) 0.1198(6) 0.5172(4) 0.0153(12) Uani 1 1 d . . . C9 C 0.1151(8) 0.1274(6) 0.5636(5) 0.0207(14) Uani 1 1 d . . . H9 H 0.1949 0.2151 0.6084 0.025 Uiso 1 1 calc R . . C10 C 0.1526(7) 0.0101(6) 0.5462(5) 0.0213(14) Uani 1 1 d . . . H10 H 0.2587 0.0182 0.5778 0.026 Uiso 1 1 calc R . . N11 N 0.2777(5) 0.4103(4) 0.1102(3) 0.0131(10) Uani 1 1 d . . . C12 C 0.4096(7) 0.3730(5) 0.1051(5) 0.0164(13) Uani 1 1 d . . . N13 N 0.4253(6) 0.3235(4) 0.0047(4) 0.0144(10) Uani 1 1 d . . . C14 C 0.2975(7) 0.3272(6) -0.0574(5) 0.0188(13) Uani 1 1 d . . . H14 H 0.2763 0.2975 -0.1314 0.023 Uiso 1 1 calc R . . C15 C 0.2072(7) 0.3820(6) 0.0080(4) 0.0175(13) Uani 1 1 d . . . H15 H 0.1110 0.3983 -0.0128 0.021 Uiso 1 1 calc R . . C16 C 0.5223(7) 0.3825(6) 0.1953(5) 0.0216(13) Uani 1 1 d . . . H16A H 0.4887 0.4250 0.2599 0.032 Uiso 1 1 calc R . . H16B H 0.6417 0.4413 0.1913 0.032 Uiso 1 1 calc R . . H16C H 0.5114 0.2874 0.1945 0.032 Uiso 1 1 calc R . . C17 C 0.5563(8) 0.2737(6) -0.0313(5) 0.0192(13) Uani 1 1 d . . . H17A H 0.6704 0.3443 0.0059 0.023 Uiso 1 1 calc R . . H17B H 0.5571 0.2652 -0.1066 0.023 Uiso 1 1 calc R . . C18 C 0.5247(7) 0.1311(6) -0.0131(4) 0.0159(12) Uani 1 1 d . . . C19 C 0.3635(7) 0.0207(5) -0.0409(4) 0.0159(12) Uani 1 1 d . . . H19 H 0.2695 0.0340 -0.0692 0.019 Uiso 1 1 calc R . . C20 C 0.3402(7) -0.1104(6) -0.0270(4) 0.0165(13) Uani 1 1 d . . . H20 H 0.2296 -0.1862 -0.0456 0.020 Uiso 1 1 calc R . . C21 C -0.1531(10) 0.0638(8) -0.2193(6) 0.045(2) Uani 1 1 d . . . H21A H -0.1114 0.1562 -0.1653 0.054 Uiso 1 1 calc R . . H21B H -0.0873 0.0774 -0.2782 0.054 Uiso 1 1 calc R . . C22 C -0.3389(10) 0.0177(7) -0.2565(6) 0.0386(18) Uani 1 1 d . . . H22B H -0.3563 0.0971 -0.2733 0.046 Uiso 1 1 calc R . . H22A H -0.4064 -0.0063 -0.1999 0.046 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0158(4) 0.0162(4) 0.0147(4) 0.0056(3) 0.0025(3) 0.0059(3) Cl1 0.0206(8) 0.0308(8) 0.0232(8) 0.0112(7) 0.0021(6) 0.0134(6) N1 0.018(2) 0.018(3) 0.016(3) 0.007(2) 0.001(2) 0.011(2) Cl2 0.0213(8) 0.0182(7) 0.0217(8) 0.0059(6) -0.0004(6) 0.0006(6) C2 0.020(3) 0.012(3) 0.015(3) 0.006(2) 0.001(2) 0.003(2) Cl3 0.0372(10) 0.0555(12) 0.0612(14) 0.0213(11) 0.0142(10) 0.0250(9) N3 0.023(3) 0.013(2) 0.017(3) 0.008(2) 0.005(2) 0.007(2) Cl4 0.0466(12) 0.0514(12) 0.0325(11) -0.0013(9) 0.0096(9) -0.0038(9) C4 0.025(3) 0.022(3) 0.017(3) 0.005(3) -0.003(3) 0.010(3) C5 0.022(3) 0.014(3) 0.023(3) 0.007(3) -0.002(3) 0.008(2) C6 0.022(3) 0.019(3) 0.019(3) 0.006(3) 0.004(3) 0.004(3) C7 0.023(3) 0.018(3) 0.020(3) 0.011(3) 0.005(3) 0.010(2) C8 0.019(3) 0.020(3) 0.014(3) 0.010(2) 0.009(2) 0.011(2) C9 0.025(3) 0.010(3) 0.020(3) 0.003(2) 0.000(3) 0.001(2) C10 0.019(3) 0.025(3) 0.023(3) 0.011(3) -0.001(3) 0.010(3) N11 0.013(2) 0.013(2) 0.014(2) 0.0041(19) -0.0024(19) 0.0055(18) C12 0.016(3) 0.006(3) 0.023(3) 0.003(2) 0.002(2) 0.000(2) N13 0.014(2) 0.011(2) 0.019(3) 0.006(2) 0.004(2) 0.0038(19) C14 0.027(3) 0.013(3) 0.016(3) 0.007(2) 0.001(3) 0.006(2) C15 0.015(3) 0.021(3) 0.020(3) 0.013(3) 0.001(2) 0.007(2) C16 0.017(3) 0.025(3) 0.028(4) 0.011(3) -0.002(3) 0.013(3) C17 0.028(3) 0.013(3) 0.025(3) 0.010(3) 0.012(3) 0.013(2) C18 0.023(3) 0.012(3) 0.010(3) 0.000(2) 0.004(2) 0.006(2) C19 0.018(3) 0.015(3) 0.017(3) 0.003(2) 0.001(2) 0.010(2) C20 0.017(3) 0.012(3) 0.014(3) 0.003(2) 0.003(2) 0.001(2) C21 0.047(5) 0.032(4) 0.042(5) 0.010(4) -0.001(4) 0.001(4) C22 0.053(5) 0.032(4) 0.033(4) 0.012(3) 0.007(4) 0.017(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N11 1.948(5) . ? Cu1 N1 1.960(5) . ? Cu1 Cl1 2.249(2) . ? Cu1 Cl2 2.2571(17) . ? N1 C2 1.334(7) . ? N1 C5 1.390(7) . ? C2 N3 1.343(7) . ? C2 C6 1.482(7) . ? Cl3 C21 1.786(8) . ? N3 C4 1.374(7) . ? N3 C7 1.477(7) . ? Cl4 C22 1.771(7) . ? C4 C5 1.350(8) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.503(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.384(8) . ? C8 C10 1.387(8) 2_556 ? C9 C10 1.376(8) . ? C9 H9 0.9500 . ? C10 C8 1.387(8) 2_556 ? C10 H10 0.9500 . ? N11 C12 1.330(7) . ? N11 C15 1.388(7) . ? C12 N13 1.349(7) . ? C12 C16 1.477(8) . ? N13 C14 1.369(7) . ? N13 C17 1.461(7) . ? C14 C15 1.358(8) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.523(8) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C20 1.372(8) 2_655 ? C18 C19 1.384(7) . ? C19 C20 1.395(8) . ? C19 H19 0.9500 . ? C20 C18 1.372(8) 2_655 ? C20 H20 0.9500 . ? C21 C22 1.494(10) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22B 0.9900 . ? C22 H22A 0.9900 . ? 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 N11 Cu1 N1 136.75(19) . . ? N11 Cu1 Cl1 99.46(14) . . ? N1 Cu1 Cl1 103.24(14) . . ? N11 Cu1 Cl2 99.65(14) . . ? N1 Cu1 Cl2 98.61(14) . . ? Cl1 Cu1 Cl2 122.21(7) . . ? C2 N1 C5 106.3(5) . . ? C2 N1 Cu1 128.0(4) . . ? C5 N1 Cu1 125.5(4) . . ? N1 C2 N3 109.7(5) . . ? N1 C2 C6 126.1(5) . . ? N3 C2 C6 124.1(5) . . ? C2 N3 C4 108.6(5) . . ? C2 N3 C7 126.1(5) . . ? C4 N3 C7 125.1(5) . . ? C5 C4 N3 106.2(5) . . ? C5 C4 H4 126.9 . . ? N3 C4 H4 126.9 . . ? C4 C5 N1 109.1(5) . . ? C4 C5 H5 125.4 . . ? N1 C5 H5 125.4 . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N3 C7 C8 110.4(5) . . ? N3 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? N3 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C9 C8 C10 118.3(5) . 2_556 ? C9 C8 C7 120.5(5) . . ? C10 C8 C7 121.2(5) 2_556 . ? C10 C9 C8 121.2(5) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C8 120.5(6) . 2_556 ? C9 C10 H10 119.8 . . ? C8 C10 H10 119.8 2_556 . ? C12 N11 C15 106.2(5) . . ? C12 N11 Cu1 123.8(4) . . ? C15 N11 Cu1 129.8(4) . . ? N11 C12 N13 110.0(5) . . ? N11 C12 C16 125.6(5) . . ? N13 C12 C16 124.4(5) . . ? C12 N13 C14 108.5(5) . . ? C12 N13 C17 125.6(5) . . ? C14 N13 C17 125.9(5) . . ? C15 C14 N13 106.2(5) . . ? C15 C14 H14 126.9 . . ? N13 C14 H14 126.9 . . ? C14 C15 N11 109.2(5) . . ? C14 C15 H15 125.4 . . ? N11 C15 H15 125.4 . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N13 C17 C18 112.0(4) . . ? N13 C17 H17A 109.2 . . ? C18 C17 H17A 109.2 . . ? N13 C17 H17B 109.2 . . ? C18 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C20 C18 C19 119.9(5) 2_655 . ? C20 C18 C17 119.3(5) 2_655 . ? C19 C18 C17 120.8(5) . . ? C18 C19 C20 119.4(5) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? C18 C20 C19 120.8(5) 2_655 . ? C18 C20 H20 119.6 2_655 . ? C19 C20 H20 119.6 . . ? C22 C21 Cl3 112.4(5) . . ? C22 C21 H21A 109.1 . . ? Cl3 C21 H21A 109.1 . . ? C22 C21 H21B 109.1 . . ? Cl3 C21 H21B 109.1 . . ? H21A C21 H21B 107.8 . . ? C21 C22 Cl4 112.2(5) . . ? C21 C22 H22B 109.2 . . ? Cl4 C22 H22B 109.2 . . ? C21 C22 H22A 109.2 . . ? Cl4 C22 H22A 109.2 . . ? H22B C22 H22A 107.9 . . ? 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 N11 Cu1 N1 C2 -67.8(6) . . . . ? Cl1 Cu1 N1 C2 52.0(5) . . . . ? Cl2 Cu1 N1 C2 178.1(5) . . . . ? N11 Cu1 N1 C5 106.0(5) . . . . ? Cl1 Cu1 N1 C5 -134.2(4) . . . . ? Cl2 Cu1 N1 C5 -8.1(5) . . . . ? C5 N1 C2 N3 1.2(6) . . . . ? Cu1 N1 C2 N3 175.9(4) . . . . ? C5 N1 C2 C6 -177.1(6) . . . . ? Cu1 N1 C2 C6 -2.4(8) . . . . ? N1 C2 N3 C4 -0.5(7) . . . . ? C6 C2 N3 C4 177.7(5) . . . . ? N1 C2 N3 C7 -175.4(5) . . . . ? C6 C2 N3 C7 2.8(9) . . . . ? C2 N3 C4 C5 -0.3(6) . . . . ? C7 N3 C4 C5 174.6(5) . . . . ? N3 C4 C5 N1 1.1(7) . . . . ? C2 N1 C5 C4 -1.4(6) . . . . ? Cu1 N1 C5 C4 -176.2(4) . . . . ? C2 N3 C7 C8 82.7(7) . . . . ? C4 N3 C7 C8 -91.4(6) . . . . ? N3 C7 C8 C9 67.4(7) . . . . ? N3 C7 C8 C10 -113.1(6) . . . 2_556 ? C10 C8 C9 C10 1.2(10) 2_556 . . . ? C7 C8 C9 C10 -179.3(6) . . . . ? C8 C9 C10 C8 -1.2(10) . . . 2_556 ? N1 Cu1 N11 C12 -55.8(5) . . . . ? Cl1 Cu1 N11 C12 -176.9(4) . . . . ? Cl2 Cu1 N11 C12 57.9(4) . . . . ? N1 Cu1 N11 C15 129.4(5) . . . . ? Cl1 Cu1 N11 C15 8.3(5) . . . . ? Cl2 Cu1 N11 C15 -116.9(4) . . . . ? C15 N11 C12 N13 0.3(6) . . . . ? Cu1 N11 C12 N13 -175.5(3) . . . . ? C15 N11 C12 C16 -179.1(5) . . . . ? Cu1 N11 C12 C16 5.0(7) . . . . ? N11 C12 N13 C14 -0.8(6) . . . . ? C16 C12 N13 C14 178.7(5) . . . . ? N11 C12 N13 C17 179.5(4) . . . . ? C16 C12 N13 C17 -1.0(8) . . . . ? C12 N13 C14 C15 0.9(6) . . . . ? C17 N13 C14 C15 -179.4(5) . . . . ? N13 C14 C15 N11 -0.7(6) . . . . ? C12 N11 C15 C14 0.3(6) . . . . ? Cu1 N11 C15 C14 175.8(4) . . . . ? C12 N13 C17 C18 72.4(7) . . . . ? C14 N13 C17 C18 -107.2(6) . . . . ? N13 C17 C18 C20 -135.5(5) . . . 2_655 ? N13 C17 C18 C19 47.4(7) . . . . ? C20 C18 C19 C20 0.4(9) 2_655 . . . ? C17 C18 C19 C20 177.5(5) . . . . ? C18 C19 C20 C18 -0.4(9) . . . 2_655 ? Cl3 C21 C22 Cl4 -68.7(7) . . . . ? _diffrn_measured_fraction_theta_max 0.891 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 1.064 _refine_diff_density_min -0.843 _refine_diff_density_rms 0.143