# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Stephen J. Loeb' _publ_contact_author_email loeb@uwindsor.ca loop_ _publ_author_name S.J.Loeb C.Caputo N.Vukotic N.Sirizzotti data_cc9 _database_code_depnum_ccdc_archive 'CCDC 822537' #TrackingRef '- CCDC-822537.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H39 N5 O' _chemical_formula_weight 701.84 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' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.985(4) _cell_length_b 7.0302(9) _cell_length_c 21.501(3) _cell_angle_alpha 90.00 _cell_angle_beta 121.0620(10) _cell_angle_gamma 90.00 _cell_volume 3623.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 266 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 25.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6560 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details sadabs _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-I CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16397 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3169 _reflns_number_gt 2336 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL XP' _computing_publication_material 'Bruker SHELXTL XCIF' _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. A disordered molecule of DMF was modeled with a 50% sof for both sites. SADI, SIMU and DELU commands were required to restrain the DMF to a chemically reasonable geometry. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+2.8653P] 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 3169 _refine_ls_number_parameters 267 _refine_ls_number_restraints 35 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1205 _refine_ls_wR_factor_gt 0.1057 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.943 _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 N1 N 0.10399(7) -1.3136(3) 0.60987(10) 0.0528(5) Uani 1 1 d . . . N2 N 0.27459(9) 0.2204(4) 0.34020(13) 0.0768(7) Uani 1 1 d . . . C1 C 0.06590(9) -1.3566(3) 0.54170(12) 0.0484(6) Uani 1 1 d . . . H1A H 0.0509 -1.4816 0.5321 0.058 Uiso 1 1 calc R . . C2 C 0.04656(8) -1.2328(3) 0.48383(11) 0.0411(5) Uani 1 1 d . . . H2A H 0.0189 -1.2732 0.4365 0.049 Uiso 1 1 calc R . . C3 C 0.06765(7) -1.0485(3) 0.49508(10) 0.0343(4) Uani 1 1 d . . . C4 C 0.10775(8) -1.0029(3) 0.56624(10) 0.0448(5) Uani 1 1 d . . . H4A H 0.1239 -0.8795 0.5776 0.054 Uiso 1 1 calc R . . C5 C 0.12404(9) -1.1369(3) 0.62013(11) 0.0520(6) Uani 1 1 d . . . H5A H 0.1516 -1.1010 0.6681 0.062 Uiso 1 1 calc R . . C6 C 0.05031(7) -0.9120(3) 0.43450(10) 0.0321(4) Uani 1 1 d . . . C7 C -0.00113(7) -0.9270(3) 0.37040(10) 0.0326(4) Uani 1 1 d . . . H7A H -0.0265 -1.0232 0.3661 0.039 Uiso 1 1 calc R . . C8 C -0.01595(7) -0.8051(2) 0.31306(10) 0.0326(4) Uani 1 1 d . . . H8A H -0.0512 -0.8204 0.2698 0.039 Uiso 1 1 calc R . . C9 C 0.01934(7) -0.6597(2) 0.31675(9) 0.0295(4) Uani 1 1 d . . . C10 C 0.07066(8) -0.6443(3) 0.38076(10) 0.0340(4) Uani 1 1 d . . . H10A H 0.0959 -0.5473 0.3852 0.041 Uiso 1 1 calc R . . C11 C 0.08585(8) -0.7676(3) 0.43839(10) 0.0358(5) Uani 1 1 d . . . H11A H 0.1212 -0.7533 0.4815 0.043 Uiso 1 1 calc R . . C12 C 0.0000 -0.5288(3) 0.2500 0.0307(6) Uani 1 2 d S . . C13 C 0.04848(7) -0.3974(2) 0.26177(9) 0.0295(4) Uani 1 1 d . . . C14 C 0.07788(7) -0.4167(3) 0.22620(10) 0.0327(4) Uani 1 1 d . . . H14A H 0.0680 -0.5142 0.1910 0.039 Uiso 1 1 calc R . . C15 C 0.12167(8) -0.2946(3) 0.24175(10) 0.0356(4) Uani 1 1 d . . . H15A H 0.1413 -0.3108 0.2169 0.043 Uiso 1 1 calc R . . C16 C 0.13767(7) -0.1503(3) 0.29233(10) 0.0329(4) Uani 1 1 d . . . C17 C 0.10723(8) -0.1286(3) 0.32682(10) 0.0348(4) Uani 1 1 d . . . H17A H 0.1166 -0.0295 0.3613 0.042 Uiso 1 1 calc R . . C18 C 0.06373(8) -0.2493(2) 0.31149(10) 0.0340(4) Uani 1 1 d . . . H18A H 0.0436 -0.2311 0.3355 0.041 Uiso 1 1 calc R . . C19 C 0.18505(8) -0.0215(3) 0.30967(10) 0.0388(5) Uani 1 1 d . . . C20 C 0.23139(8) -0.0862(3) 0.30932(12) 0.0514(6) Uani 1 1 d . . . H20A H 0.2336 -0.2154 0.2981 0.062 Uiso 1 1 calc R . . C21 C 0.27457(10) 0.0377(4) 0.32541(15) 0.0707(8) Uani 1 1 d . . . H21A H 0.3064 -0.0115 0.3259 0.085 Uiso 1 1 calc R . . C22 C 0.22952(11) 0.2819(4) 0.33978(15) 0.0699(8) Uani 1 1 d . . . H22A H 0.2280 0.4127 0.3498 0.084 Uiso 1 1 calc R . . C23 C 0.18460(9) 0.1687(3) 0.32582(12) 0.0509(6) Uani 1 1 d . . . H23A H 0.1539 0.2209 0.3273 0.061 Uiso 1 1 calc R . . N1S N 0.256(2) -0.250(3) 0.498(4) 0.090(3) Uani 0.50 1 d PDU A -1 O1S O 0.2108(3) -0.5448(14) 0.4767(4) 0.165(3) Uani 0.50 1 d PU A -1 C1S C 0.2981(3) -0.3141(13) 0.4862(3) 0.095(2) Uani 0.50 1 d PDU A -1 H1SA H 0.2943 -0.4515 0.4772 0.142 Uiso 0.50 1 calc PR A -1 H1SB H 0.3346 -0.2867 0.5293 0.142 Uiso 0.50 1 calc PR A -1 H1SC H 0.2950 -0.2482 0.4441 0.142 Uiso 0.50 1 calc PR A -1 C3S C 0.2145(4) -0.376(2) 0.4915(5) 0.127(3) Uani 0.50 1 d PDU A -1 H3SA H 0.1868 -0.3241 0.4996 0.152 Uiso 0.50 1 calc PR A -1 C2S C 0.2527(5) -0.0580(17) 0.5134(5) 0.139(4) Uani 0.50 1 d PDU A -1 H2SA H 0.2207 -0.0388 0.5197 0.209 Uiso 0.50 1 calc PR A -1 H2SB H 0.2482 0.0211 0.4733 0.209 Uiso 0.50 1 calc PR A -1 H2SC H 0.2871 -0.0222 0.5582 0.209 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 N1 0.0467(11) 0.0649(13) 0.0475(11) 0.0178(10) 0.0248(9) 0.0054(10) N2 0.0511(13) 0.0748(16) 0.0940(18) 0.0060(14) 0.0300(13) -0.0228(12) C1 0.0461(12) 0.0463(13) 0.0528(14) 0.0125(11) 0.0256(11) 0.0002(10) C2 0.0395(11) 0.0410(12) 0.0396(11) 0.0052(9) 0.0181(10) -0.0010(9) C3 0.0325(10) 0.0391(11) 0.0341(10) 0.0008(8) 0.0192(9) 0.0018(8) C4 0.0461(12) 0.0501(13) 0.0367(11) -0.0006(10) 0.0203(10) -0.0044(10) C5 0.0475(13) 0.0700(16) 0.0328(11) 0.0054(11) 0.0166(10) -0.0009(12) C6 0.0348(10) 0.0305(10) 0.0342(10) -0.0019(8) 0.0200(9) 0.0018(8) C7 0.0327(10) 0.0289(10) 0.0388(10) -0.0009(8) 0.0204(9) -0.0029(8) C8 0.0307(10) 0.0293(10) 0.0346(10) -0.0011(8) 0.0145(8) -0.0007(8) C9 0.0310(9) 0.0259(9) 0.0348(10) -0.0021(8) 0.0192(8) 0.0020(7) C10 0.0342(10) 0.0290(10) 0.0396(11) -0.0026(8) 0.0197(9) -0.0041(8) C11 0.0342(10) 0.0353(10) 0.0332(10) -0.0023(8) 0.0141(9) -0.0027(8) C12 0.0302(13) 0.0268(13) 0.0365(14) 0.000 0.0181(12) 0.000 C13 0.0293(9) 0.0253(9) 0.0337(10) 0.0016(8) 0.0161(8) 0.0023(7) C14 0.0351(10) 0.0304(10) 0.0351(10) -0.0018(8) 0.0199(9) -0.0002(8) C15 0.0344(10) 0.0378(11) 0.0411(11) 0.0020(9) 0.0241(9) 0.0028(9) C16 0.0306(10) 0.0308(10) 0.0358(10) 0.0041(8) 0.0161(8) 0.0013(8) C17 0.0392(11) 0.0282(10) 0.0358(10) -0.0030(8) 0.0185(9) -0.0017(8) C18 0.0377(10) 0.0313(10) 0.0408(11) -0.0012(8) 0.0258(9) -0.0010(8) C19 0.0345(11) 0.0430(12) 0.0362(11) 0.0062(9) 0.0162(9) -0.0035(9) C20 0.0364(11) 0.0523(13) 0.0636(15) 0.0118(11) 0.0246(11) -0.0022(10) C21 0.0402(13) 0.0745(19) 0.094(2) 0.0245(16) 0.0321(14) -0.0005(13) C22 0.0656(17) 0.0576(16) 0.0802(19) -0.0104(14) 0.0331(15) -0.0259(14) C23 0.0475(13) 0.0461(13) 0.0557(14) -0.0056(11) 0.0243(11) -0.0130(10) N1S 0.063(15) 0.140(4) 0.045(7) -0.013(3) 0.013(10) 0.000(4) O1S 0.111(5) 0.217(8) 0.148(6) -0.067(6) 0.053(4) -0.058(5) C1S 0.074(4) 0.138(6) 0.058(4) 0.000(4) 0.024(3) 0.011(4) C3S 0.077(5) 0.202(9) 0.067(5) -0.015(7) 0.013(5) -0.030(7) C2S 0.109(7) 0.182(8) 0.089(6) -0.064(7) 0.024(6) -0.009(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 N1 C1 1.328(3) . ? N1 C5 1.334(3) . ? N2 C21 1.323(4) . ? N2 C22 1.329(3) . ? C1 C2 1.380(3) . ? C2 C3 1.392(3) . ? C3 C4 1.390(3) . ? C3 C6 1.483(3) . ? C4 C5 1.376(3) . ? C6 C7 1.391(3) . ? C6 C11 1.393(3) . ? C7 C8 1.378(3) . ? C8 C9 1.395(2) . ? C9 C10 1.389(2) . ? C9 C12 1.549(2) . ? C10 C11 1.387(3) . ? C12 C9 1.549(2) 2 ? C12 C13 1.551(2) 2 ? C12 C13 1.551(2) . ? C13 C14 1.389(2) . ? C13 C18 1.392(2) . ? C14 C15 1.388(3) . ? C15 C16 1.382(3) . ? C16 C17 1.397(3) . ? C16 C19 1.485(3) . ? C17 C18 1.377(2) . ? C19 C20 1.378(3) . ? C19 C23 1.384(3) . ? C20 C21 1.381(3) . ? C22 C23 1.384(3) . ? N1S C3S 1.396(12) . ? N1S C2S 1.406(12) . ? N1S C1S 1.411(11) . ? O1S C3S 1.222(14) . ? 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 C1 N1 C5 115.11(18) . . ? C21 N2 C22 115.6(2) . . ? N1 C1 C2 124.7(2) . . ? C1 C2 C3 119.76(19) . . ? C4 C3 C2 115.80(18) . . ? C4 C3 C6 121.99(18) . . ? C2 C3 C6 122.16(17) . . ? C5 C4 C3 119.8(2) . . ? N1 C5 C4 124.7(2) . . ? C7 C6 C11 117.16(17) . . ? C7 C6 C3 121.55(17) . . ? C11 C6 C3 121.25(16) . . ? C8 C7 C6 121.27(17) . . ? C7 C8 C9 121.83(17) . . ? C10 C9 C8 116.97(16) . . ? C10 C9 C12 124.07(15) . . ? C8 C9 C12 118.95(15) . . ? C11 C10 C9 121.32(17) . . ? C10 C11 C6 121.44(17) . . ? C9 C12 C9 107.08(19) . 2 ? C9 C12 C13 111.32(9) . 2 ? C9 C12 C13 110.18(9) 2 2 ? C9 C12 C13 110.18(9) . . ? C9 C12 C13 111.32(9) 2 . ? C13 C12 C13 106.82(19) 2 . ? C14 C13 C18 117.53(16) . . ? C14 C13 C12 124.65(15) . . ? C18 C13 C12 117.83(14) . . ? C15 C14 C13 120.44(17) . . ? C16 C15 C14 122.05(17) . . ? C15 C16 C17 117.33(17) . . ? C15 C16 C19 121.97(17) . . ? C17 C16 C19 120.70(17) . . ? C18 C17 C16 120.78(17) . . ? C17 C18 C13 121.83(17) . . ? C20 C19 C23 116.79(19) . . ? C20 C19 C16 121.24(19) . . ? C23 C19 C16 121.96(18) . . ? C19 C20 C21 119.7(2) . . ? N2 C21 C20 124.4(2) . . ? N2 C22 C23 124.6(3) . . ? C22 C23 C19 119.0(2) . . ? C3S N1S C2S 119.0(11) . . ? C3S N1S C1S 120.7(12) . . ? C2S N1S C1S 120.3(11) . . ? O1S C3S N1S 126.5(14) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.162 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.033 # Attachment '- CCDC-822539.cif' data_cc15 _database_code_depnum_ccdc_archive 'CCDC 822538' #TrackingRef '- CCDC-822539.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C116 H106 Cl6 Cu3 N14 O6' _chemical_formula_weight 2195.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.308(12) _cell_length_b 13.967(7) _cell_length_c 32.201(17) _cell_angle_alpha 90.00 _cell_angle_beta 106.519(9) _cell_angle_gamma 90.00 _cell_volume 10058(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 562 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 25.00 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4548 _exptl_absorpt_coefficient_mu 0.845 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5535 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details sadabs _exptl_special_details ; Crystals were of poor quality and only weakly diffracting resulting in a relatively high value for Rint. Systematic absences were consistent with space groups C2/c and Cc but diffraction statistics indicated a centrosymmetric space group; C2/c. Solutions in both space groups were attempted but only C2/c gave a satisfactory solution. ; _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-I CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 46413 _diffrn_reflns_av_R_equivalents 0.2774 _diffrn_reflns_av_sigmaI/netI 0.3645 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8817 _reflns_number_gt 1932 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL XP' _computing_publication_material 'Bruker SHELXTL XCIF' loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.000 0.009 1734 869 ' ' 2 0.000 0.500 0.050 1734 869 ' ' _platon_squeeze_details ; The unit cell contains an estimated 24 molecules of DMF which have been treated as a diffuse contribution to the overall scattering without specific atom positions by SQUEEZE/PLATON. 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. Separate SIMU commands were employed to restraints displacement parameters on individual aromatic rings. It was also necessary to employ the ISOR command to restrain the displacment parameters for C14, C22, C36 and C43. ; _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^)+(0.0692P)^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 8817 _refine_ls_number_parameters 486 _refine_ls_number_restraints 312 _refine_ls_R_factor_all 0.2889 _refine_ls_R_factor_gt 0.0779 _refine_ls_wR_factor_ref 0.2296 _refine_ls_wR_factor_gt 0.1703 _refine_ls_goodness_of_fit_ref 0.737 _refine_ls_restrained_S_all 0.736 _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 -0.5000 0.49723(15) 1.2500 0.0568(6) Uani 1 2 d S . . Cu2 Cu -0.32396(6) 0.50395(11) 1.17668(5) 0.0630(5) Uani 1 1 d . . . Cl1 Cl -0.40337(11) 0.5024(2) 1.21736(9) 0.0635(8) Uani 1 1 d . . . Cl2 Cl -0.29447(15) 0.6575(2) 1.16410(12) 0.0768(13) Uani 1 1 d . . . Cl3 Cl -0.29808(15) 0.3501(2) 1.16021(11) 0.0713(12) Uani 1 1 d . . . N1 N -0.7318(3) 0.4996(9) 1.2620(3) 0.052(2) Uani 1 1 d . . . C2 C -0.7366(7) 0.4166(10) 1.2408(5) 0.088(6) Uani 1 1 d . . . H2A H -0.7272 0.3603 1.2566 0.106 Uiso 1 1 calc R . . C3 C -0.7547(7) 0.4115(8) 1.1969(5) 0.080(5) Uani 1 1 d . . . H3A H -0.7595 0.3513 1.1840 0.096 Uiso 1 1 calc R . . C4 C -0.7669(4) 0.4943(9) 1.1695(4) 0.054(3) Uani 1 1 d . . . C5 C -0.7604(5) 0.5810(8) 1.1924(4) 0.051(4) Uani 1 1 d . . . H5A H -0.7657 0.6387 1.1773 0.061 Uiso 1 1 calc R . . C6 C -0.7462(6) 0.5812(10) 1.2368(5) 0.072(5) Uani 1 1 d . . . H6A H -0.7462 0.6395 1.2507 0.086 Uiso 1 1 calc R . . C7 C -0.7741(4) 0.4942(9) 1.1223(4) 0.054(3) Uani 1 1 d . . . C8 C -0.7925(6) 0.5776(8) 1.0973(5) 0.070(4) Uani 1 1 d . . . H8A H -0.8017 0.6333 1.1100 0.084 Uiso 1 1 calc R . . C9 C -0.7967(5) 0.5750(8) 1.0534(4) 0.063(4) Uani 1 1 d . . . H9A H -0.8123 0.6280 1.0364 0.075 Uiso 1 1 calc R . . C10 C -0.7785(4) 0.4965(9) 1.0335(3) 0.055(3) Uani 1 1 d . . . C11 C -0.7612(5) 0.4157(7) 1.0601(4) 0.052(4) Uani 1 1 d . . . H11A H -0.7510 0.3599 1.0481 0.062 Uiso 1 1 calc R . . C12 C -0.7588(5) 0.4166(8) 1.1024(4) 0.056(4) Uani 1 1 d . . . H12A H -0.7462 0.3615 1.1187 0.067 Uiso 1 1 calc R . . N13 N -0.9565(5) 0.9030(6) 0.7937(3) 0.048(3) Uani 1 1 d . . . C14 C -0.9851(5) 0.8234(7) 0.8048(4) 0.049(3) Uani 1 1 d U . . H14A H -1.0252 0.8131 0.7900 0.059 Uiso 1 1 calc R . . C15 C -0.9572(5) 0.7597(7) 0.8364(4) 0.055(4) Uani 1 1 d . . . H15A H -0.9779 0.7066 0.8422 0.066 Uiso 1 1 calc R . . C16 C -0.8972(6) 0.7747(9) 0.8602(5) 0.062(4) Uani 1 1 d . . . C17 C -0.8663(5) 0.8567(8) 0.8498(4) 0.060(4) Uani 1 1 d . . . H17A H -0.8270 0.8709 0.8652 0.072 Uiso 1 1 calc R . . C18 C -0.8985(6) 0.9137(8) 0.8153(4) 0.057(4) Uani 1 1 d . . . H18A H -0.8779 0.9634 0.8067 0.068 Uiso 1 1 calc R . . C19 C -0.8645(6) 0.7086(8) 0.8959(4) 0.052(4) Uani 1 1 d . . . C20 C -0.8032(6) 0.6943(8) 0.9021(3) 0.045(3) Uani 1 1 d . . . H20A H -0.7838 0.7290 0.8855 0.055 Uiso 1 1 calc R . . C21 C -0.7715(6) 0.6318(8) 0.9316(4) 0.049(4) Uani 1 1 d . . . H21A H -0.7315 0.6199 0.9337 0.059 Uiso 1 1 calc R . . C22 C -0.7991(5) 0.5852(7) 0.9588(4) 0.040(3) Uani 1 1 d U . . C23 C -0.8604(6) 0.5983(7) 0.9525(5) 0.078(5) Uani 1 1 d . . . H23A H -0.8798 0.5653 0.9697 0.094 Uiso 1 1 calc R . . C24 C -0.8923(6) 0.6600(7) 0.9209(4) 0.058(4) Uani 1 1 d . . . H24A H -0.9332 0.6683 0.9168 0.070 Uiso 1 1 calc R . . N25 N -0.3925(4) 0.5164(9) 1.1233(3) 0.061(3) Uani 1 1 d . . . C26 C -0.4120(7) 0.4486(10) 1.0935(5) 0.076(5) Uani 1 1 d . . . H26A H -0.3867 0.3970 1.0937 0.091 Uiso 1 1 calc R . . C27 C -0.4672(8) 0.4490(8) 1.0620(4) 0.079(5) Uani 1 1 d . . . H27A H -0.4765 0.4010 1.0412 0.095 Uiso 1 1 calc R . . C28 C -0.5082(7) 0.5208(9) 1.0618(4) 0.062(4) Uani 1 1 d . . . C29 C -0.4845(6) 0.5913(9) 1.0922(5) 0.072(4) Uani 1 1 d . . . H29A H -0.5085 0.6446 1.0922 0.086 Uiso 1 1 calc R . . C30 C -0.4313(6) 0.5905(9) 1.1211(5) 0.068(4) Uani 1 1 d U . . H30A H -0.4201 0.6415 1.1402 0.082 Uiso 1 1 calc R . . C31 C -0.5730(6) 0.5194(7) 1.0351(4) 0.050(3) Uani 1 1 d . . . C32 C -0.6082(6) 0.5997(8) 1.0327(4) 0.054(4) Uani 1 1 d . . . H32A H -0.5902 0.6580 1.0427 0.065 Uiso 1 1 calc R . . C33 C -0.6691(7) 0.5950(8) 1.0159(4) 0.066(4) Uani 1 1 d . . . H33A H -0.6917 0.6504 1.0146 0.080 Uiso 1 1 calc R . . C34 C -0.6986(5) 0.5081(9) 1.0003(3) 0.055(3) Uani 1 1 d . . . C35 C -0.6625(6) 0.4299(8) 1.0009(4) 0.057(4) Uani 1 1 d . . . H35A H -0.6794 0.3718 0.9896 0.068 Uiso 1 1 calc R . . C36 C -0.6017(6) 0.4372(8) 1.0182(4) 0.058(4) Uani 1 1 d . . . H36A H -0.5787 0.3828 1.0183 0.070 Uiso 1 1 calc R . . N37 N -0.9623(5) 0.1058(6) 0.7949(4) 0.070(3) Uani 1 1 d . . . C38 C -0.9210(6) 0.1689(7) 0.7876(4) 0.083(5) Uani 1 1 d . . . H38A H -0.9154 0.1736 0.7602 0.100 Uiso 1 1 calc R . . C39 C -0.8882(6) 0.2246(8) 0.8207(5) 0.085(5) Uani 1 1 d . . . H39A H -0.8608 0.2674 0.8149 0.102 Uiso 1 1 calc R . . C40 C -0.8936(6) 0.2208(7) 0.8634(4) 0.052(4) Uani 1 1 d . . . C41 C -0.9350(6) 0.1586(8) 0.8685(4) 0.063(4) Uani 1 1 d . . . H41A H -0.9417 0.1543 0.8955 0.075 Uiso 1 1 calc R . . C42 C -0.9673(6) 0.1019(9) 0.8363(5) 0.070(4) Uani 1 1 d . . . H42A H -0.9941 0.0586 0.8425 0.084 Uiso 1 1 calc R . . C43 C -0.8585(6) 0.2821(7) 0.8969(4) 0.045(3) Uani 1 1 d U . . C44 C -0.8755(6) 0.3031(7) 0.9343(4) 0.069(5) Uani 1 1 d . . . H44A H -0.9083 0.2717 0.9389 0.083 Uiso 1 1 calc R . . C45 C -0.8457(6) 0.3672(8) 0.9637(4) 0.066(4) Uani 1 1 d . . . H45A H -0.8597 0.3802 0.9875 0.080 Uiso 1 1 calc R . . C46 C -0.7935(6) 0.4162(8) 0.9603(5) 0.070(5) Uani 1 1 d . . . C47 C -0.7763(6) 0.3913(8) 0.9235(5) 0.070(4) Uani 1 1 d . . . H47A H -0.7410 0.4177 0.9206 0.083 Uiso 1 1 calc R . . C48 C -0.8088(5) 0.3282(8) 0.8900(4) 0.062(4) Uani 1 1 d . . . H48A H -0.7975 0.3184 0.8649 0.074 Uiso 1 1 calc R . . C49 C -0.7676(5) 0.5050(8) 0.9875(3) 0.052(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0723(13) 0.0225(9) 0.0950(15) 0.000 0.0554(12) 0.000 Cu2 0.0739(10) 0.0436(8) 0.0908(12) 0.0163(11) 0.0547(10) 0.0129(11) Cl1 0.073(2) 0.0440(14) 0.095(2) 0.003(2) 0.0599(18) 0.001(2) Cl2 0.090(3) 0.060(2) 0.109(3) 0.022(2) 0.075(3) 0.001(2) Cl3 0.081(3) 0.062(2) 0.076(3) 0.0084(19) 0.031(2) 0.034(2) N1 0.048(6) 0.050(5) 0.062(6) -0.010(8) 0.023(5) -0.017(7) C2 0.137(15) 0.067(11) 0.089(13) -0.055(10) 0.078(12) -0.071(10) C3 0.147(15) 0.024(8) 0.091(13) 0.002(8) 0.070(12) -0.027(9) C4 0.069(8) 0.033(6) 0.071(8) -0.034(9) 0.036(7) -0.006(8) C5 0.045(9) 0.042(8) 0.074(11) -0.005(8) 0.030(8) 0.005(6) C6 0.081(11) 0.063(10) 0.078(13) -0.058(9) 0.035(10) -0.010(9) C7 0.065(8) 0.026(6) 0.082(9) 0.010(9) 0.037(7) -0.005(8) C8 0.099(12) 0.040(8) 0.092(12) -0.026(8) 0.062(10) -0.016(8) C9 0.071(10) 0.038(8) 0.076(11) 0.013(7) 0.015(9) -0.007(7) C10 0.071(8) 0.024(6) 0.084(8) 0.008(9) 0.044(7) 0.015(8) C11 0.081(10) 0.019(6) 0.068(10) 0.006(6) 0.042(8) 0.016(6) C12 0.072(10) 0.034(7) 0.078(11) 0.004(7) 0.050(9) -0.006(7) N13 0.072(8) 0.017(5) 0.072(8) 0.010(5) 0.049(7) 0.012(5) C14 0.023(6) 0.041(6) 0.088(7) 0.006(6) 0.024(6) 0.013(5) C15 0.034(8) 0.020(6) 0.111(12) 0.013(7) 0.022(8) 0.005(6) C16 0.061(11) 0.049(9) 0.098(13) -0.002(9) 0.058(10) 0.005(8) C17 0.048(9) 0.053(8) 0.095(11) 0.009(8) 0.045(9) -0.013(7) C18 0.043(9) 0.034(7) 0.092(11) 0.001(7) 0.017(9) 0.003(7) C19 0.063(10) 0.032(7) 0.080(11) 0.013(7) 0.052(9) 0.026(7) C20 0.066(10) 0.057(8) 0.017(7) -0.007(6) 0.017(7) -0.020(7) C21 0.054(9) 0.048(8) 0.057(9) -0.005(7) 0.037(8) -0.018(7) C22 0.056(7) 0.018(5) 0.056(7) 0.000(5) 0.031(6) 0.012(5) C23 0.110(12) 0.009(6) 0.146(14) 0.006(7) 0.085(11) 0.016(7) C24 0.062(9) 0.026(7) 0.101(12) 0.006(7) 0.045(9) 0.001(7) N25 0.029(6) 0.086(10) 0.066(8) 0.015(7) 0.008(6) -0.017(7) C26 0.085(14) 0.083(11) 0.058(12) 0.051(10) 0.018(10) 0.033(10) C27 0.150(15) 0.069(9) 0.049(10) 0.031(7) 0.075(11) 0.060(10) C28 0.083(11) 0.054(10) 0.074(10) 0.029(8) 0.061(9) 0.033(9) C29 0.054(11) 0.038(8) 0.116(13) 0.022(9) 0.010(10) 0.008(7) C30 0.049(7) 0.053(7) 0.104(9) 0.007(6) 0.024(7) 0.021(6) C31 0.045(9) 0.037(9) 0.083(9) 0.002(7) 0.044(8) -0.002(6) C32 0.065(10) 0.042(7) 0.063(10) 0.022(7) 0.032(9) 0.034(7) C33 0.087(11) 0.035(8) 0.088(11) 0.017(7) 0.043(10) 0.023(8) C34 0.074(8) 0.018(6) 0.094(9) 0.009(8) 0.062(7) 0.001(8) C35 0.063(10) 0.047(8) 0.079(10) -0.009(7) 0.051(9) -0.007(7) C36 0.056(10) 0.031(8) 0.103(12) 0.022(7) 0.048(9) 0.012(7) N37 0.099(10) 0.018(6) 0.113(10) -0.010(6) 0.063(9) 0.005(6) C38 0.151(14) 0.024(7) 0.109(12) -0.016(8) 0.092(12) -0.034(8) C39 0.115(13) 0.051(9) 0.113(13) -0.042(9) 0.068(11) -0.037(8) C40 0.099(12) 0.018(6) 0.067(10) -0.011(6) 0.069(10) -0.009(7) C41 0.087(11) 0.044(8) 0.070(11) 0.002(7) 0.043(9) -0.001(8) C42 0.065(10) 0.071(10) 0.089(12) 0.016(9) 0.048(10) 0.008(8) C43 0.064(7) 0.021(5) 0.062(7) -0.010(5) 0.038(6) 0.012(5) C44 0.096(11) 0.016(6) 0.132(13) 0.008(7) 0.092(11) -0.010(7) C45 0.127(13) 0.023(7) 0.076(10) -0.009(7) 0.072(10) -0.010(8) C46 0.103(11) 0.034(7) 0.114(12) 0.016(8) 0.095(10) 0.007(8) C47 0.067(10) 0.045(8) 0.123(13) -0.030(8) 0.069(10) -0.002(7) C48 0.075(10) 0.040(7) 0.105(12) -0.013(7) 0.082(10) -0.009(7) C49 0.081(8) 0.018(5) 0.081(8) -0.029(8) 0.060(7) -0.018(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 N13 2.033(9) 8_566 ? Cu1 N13 2.033(9) 7_367 ? Cu1 N37 2.051(10) 7_357 ? Cu1 N37 2.051(10) 8_556 ? Cu1 Cl1 2.742(3) 2_457 ? Cu1 Cl1 2.742(3) . ? Cu2 N25 1.991(10) . ? Cu2 N1 2.031(8) 2_457 ? Cu2 Cl2 2.322(4) . ? Cu2 Cl3 2.332(4) . ? Cu2 Cl1 2.551(3) . ? N1 C2 1.333(13) . ? N1 C6 1.384(15) . ? N1 Cu2 2.031(8) 2_457 ? C2 C3 1.354(16) . ? C2 H2A 0.9300 . ? C3 C4 1.434(15) . ? C3 H3A 0.9300 . ? C4 C5 1.402(14) . ? C4 C7 1.482(13) . ? C5 C6 1.371(15) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C12 1.357(13) . ? C7 C8 1.412(15) . ? C8 C9 1.389(14) . ? C8 H8A 0.9300 . ? C9 C10 1.395(14) . ? C9 H9A 0.9300 . ? C10 C11 1.404(13) . ? C10 C49 1.576(13) . ? C11 C12 1.345(13) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? N13 C18 1.342(12) . ? N13 C14 1.393(12) . ? N13 Cu1 2.033(9) 7_367 ? C14 C15 1.370(13) . ? C14 H14A 0.9300 . ? C15 C16 1.404(15) . ? C15 H15A 0.9300 . ? C16 C17 1.441(14) . ? C16 C19 1.502(15) . ? C17 C18 1.396(14) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 C24 1.351(14) . ? C19 C20 1.399(14) . ? C20 C21 1.344(13) . ? C20 H20A 0.9300 . ? C21 C22 1.385(13) . ? C21 H21A 0.9300 . ? C22 C23 1.398(14) . ? C22 C49 1.503(14) . ? C23 C24 1.378(15) . ? C23 H23A 0.9300 . ? C24 H24A 0.9300 . ? N25 C26 1.333(15) . ? N25 C30 1.362(13) . ? C26 C27 1.392(16) . ? C26 H26A 0.9300 . ? C27 C28 1.383(14) . ? C27 H27A 0.9300 . ? C28 C29 1.387(15) . ? C28 C31 1.510(16) . ? C29 C30 1.321(14) . ? C29 H29A 0.9300 . ? C30 H30A 0.9300 . ? C31 C36 1.362(14) . ? C31 C32 1.379(12) . ? C32 C33 1.369(14) . ? C32 H32A 0.9300 . ? C33 C34 1.414(14) . ? C33 H33A 0.9300 . ? C34 C35 1.376(14) . ? C34 C49 1.542(13) . ? C35 C36 1.368(14) . ? C35 H35A 0.9300 . ? C36 H36A 0.9300 . ? N37 C38 1.372(13) . ? N37 C42 1.373(13) . ? N37 Cu1 2.051(10) 7_357 ? C38 C39 1.365(15) . ? C38 H38A 0.9300 . ? C39 C40 1.414(15) . ? C39 H39A 0.9300 . ? C40 C41 1.342(14) . ? C40 C43 1.436(14) . ? C41 C42 1.349(15) . ? C41 H41A 0.9300 . ? C42 H42A 0.9300 . ? C43 C48 1.395(13) . ? C43 C44 1.400(14) . ? C44 C45 1.344(15) . ? C44 H44A 0.9300 . ? C45 C46 1.426(15) . ? C45 H45A 0.9300 . ? C46 C47 1.398(14) . ? C46 C49 1.538(15) . ? C47 C48 1.431(15) . ? C47 H47A 0.9300 . ? C48 H48A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N13 Cu1 N13 93.4(6) 8_566 7_367 ? N13 Cu1 N37 175.7(5) 8_566 7_357 ? N13 Cu1 N37 88.0(4) 7_367 7_357 ? N13 Cu1 N37 88.0(4) 8_566 8_556 ? N13 Cu1 N37 175.7(5) 7_367 8_556 ? N37 Cu1 N37 90.9(6) 7_357 8_556 ? N13 Cu1 Cl1 91.1(3) 8_566 2_457 ? N13 Cu1 Cl1 86.8(3) 7_367 2_457 ? N37 Cu1 Cl1 93.1(3) 7_357 2_457 ? N37 Cu1 Cl1 89.0(3) 8_556 2_457 ? N13 Cu1 Cl1 86.8(3) 8_566 . ? N13 Cu1 Cl1 91.1(3) 7_367 . ? N37 Cu1 Cl1 89.0(3) 7_357 . ? N37 Cu1 Cl1 93.1(3) 8_556 . ? Cl1 Cu1 Cl1 176.98(16) 2_457 . ? N25 Cu2 N1 166.9(4) . 2_457 ? N25 Cu2 Cl2 88.5(3) . . ? N1 Cu2 Cl2 93.3(4) 2_457 . ? N25 Cu2 Cl3 94.6(4) . . ? N1 Cu2 Cl3 93.3(3) 2_457 . ? Cl2 Cu2 Cl3 134.62(11) . . ? N25 Cu2 Cl1 85.5(3) . . ? N1 Cu2 Cl1 81.8(2) 2_457 . ? Cl2 Cu2 Cl1 113.00(12) . . ? Cl3 Cu2 Cl1 112.37(12) . . ? Cu2 Cl1 Cu1 172.03(13) . . ? C2 N1 C6 116.4(9) . . ? C2 N1 Cu2 117.5(11) . 2_457 ? C6 N1 Cu2 121.7(9) . 2_457 ? N1 C2 C3 122.4(14) . . ? N1 C2 H2A 118.8 . . ? C3 C2 H2A 118.8 . . ? C2 C3 C4 123.1(12) . . ? C2 C3 H3A 118.4 . . ? C4 C3 H3A 118.4 . . ? C5 C4 C3 113.6(10) . . ? C5 C4 C7 120.2(13) . . ? C3 C4 C7 125.1(12) . . ? C6 C5 C4 120.4(12) . . ? C6 C5 H5A 119.8 . . ? C4 C5 H5A 119.8 . . ? C5 C6 N1 123.7(11) . . ? C5 C6 H6A 118.1 . . ? N1 C6 H6A 118.1 . . ? C12 C7 C8 118.0(10) . . ? C12 C7 C4 121.1(12) . . ? C8 C7 C4 120.7(12) . . ? C9 C8 C7 118.7(11) . . ? C9 C8 H8A 120.7 . . ? C7 C8 H8A 120.7 . . ? C8 C9 C10 123.0(11) . . ? C8 C9 H9A 118.5 . . ? C10 C9 H9A 118.5 . . ? C9 C10 C11 115.1(10) . . ? C9 C10 C49 121.5(11) . . ? C11 C10 C49 122.5(10) . . ? C12 C11 C10 122.1(10) . . ? C12 C11 H11A 119.0 . . ? C10 C11 H11A 119.0 . . ? C11 C12 C7 122.9(11) . . ? C11 C12 H12A 118.5 . . ? C7 C12 H12A 118.5 . . ? C18 N13 C14 116.1(10) . . ? C18 N13 Cu1 120.8(8) . 7_367 ? C14 N13 Cu1 122.9(9) . 7_367 ? C15 C14 N13 123.3(11) . . ? C15 C14 H14A 118.4 . . ? N13 C14 H14A 118.4 . . ? C14 C15 C16 119.7(11) . . ? C14 C15 H15A 120.1 . . ? C16 C15 H15A 120.1 . . ? C15 C16 C17 118.5(13) . . ? C15 C16 C19 122.3(11) . . ? C17 C16 C19 119.2(13) . . ? C18 C17 C16 116.6(12) . . ? C18 C17 H17A 121.7 . . ? C16 C17 H17A 121.7 . . ? N13 C18 C17 125.6(11) . . ? N13 C18 H18A 117.2 . . ? C17 C18 H18A 117.2 . . ? C24 C19 C20 119.0(13) . . ? C24 C19 C16 122.7(12) . . ? C20 C19 C16 118.2(12) . . ? C21 C20 C19 121.8(12) . . ? C21 C20 H20A 119.1 . . ? C19 C20 H20A 119.1 . . ? C20 C21 C22 119.4(12) . . ? C20 C21 H21A 120.3 . . ? C22 C21 H21A 120.3 . . ? C21 C22 C23 119.0(12) . . ? C21 C22 C49 120.4(11) . . ? C23 C22 C49 119.1(11) . . ? C24 C23 C22 120.2(12) . . ? C24 C23 H23A 119.9 . . ? C22 C23 H23A 119.9 . . ? C19 C24 C23 120.3(13) . . ? C19 C24 H24A 119.8 . . ? C23 C24 H24A 119.8 . . ? C26 N25 C30 114.6(12) . . ? C26 N25 Cu2 125.7(11) . . ? C30 N25 Cu2 118.0(11) . . ? N25 C26 C27 125.2(14) . . ? N25 C26 H26A 117.4 . . ? C27 C26 H26A 117.4 . . ? C28 C27 C26 120.0(14) . . ? C28 C27 H27A 120.0 . . ? C26 C27 H27A 120.0 . . ? C27 C28 C29 112.1(14) . . ? C27 C28 C31 124.8(14) . . ? C29 C28 C31 122.9(11) . . ? C30 C29 C28 126.5(13) . . ? C30 C29 H29A 116.7 . . ? C28 C29 H29A 116.7 . . ? C29 C30 N25 121.3(13) . . ? C29 C30 H30A 119.3 . . ? N25 C30 H30A 119.3 . . ? C36 C31 C32 116.6(12) . . ? C36 C31 C28 122.5(11) . . ? C32 C31 C28 120.2(11) . . ? C33 C32 C31 121.0(13) . . ? C33 C32 H32A 119.5 . . ? C31 C32 H32A 119.5 . . ? C32 C33 C34 121.8(11) . . ? C32 C33 H33A 119.1 . . ? C34 C33 H33A 119.1 . . ? C35 C34 C33 116.3(11) . . ? C35 C34 C49 124.6(12) . . ? C33 C34 C49 118.9(11) . . ? C36 C35 C34 120.3(11) . . ? C36 C35 H35A 119.9 . . ? C34 C35 H35A 119.9 . . ? C31 C36 C35 124.0(11) . . ? C31 C36 H36A 118.0 . . ? C35 C36 H36A 118.0 . . ? C38 N37 C42 116.7(12) . . ? C38 N37 Cu1 120.7(9) . 7_357 ? C42 N37 Cu1 121.2(9) . 7_357 ? C39 C38 N37 119.8(12) . . ? C39 C38 H38A 120.1 . . ? N37 C38 H38A 120.1 . . ? C38 C39 C40 123.5(12) . . ? C38 C39 H39A 118.3 . . ? C40 C39 H39A 118.3 . . ? C41 C40 C39 114.1(12) . . ? C41 C40 C43 124.7(12) . . ? C39 C40 C43 121.2(11) . . ? C40 C41 C42 123.4(13) . . ? C40 C41 H41A 118.3 . . ? C42 C41 H41A 118.3 . . ? C41 C42 N37 122.5(12) . . ? C41 C42 H42A 118.8 . . ? N37 C42 H42A 118.8 . . ? C48 C43 C44 119.3(12) . . ? C48 C43 C40 118.4(11) . . ? C44 C43 C40 122.0(12) . . ? C45 C44 C43 122.0(11) . . ? C45 C44 H44A 119.0 . . ? C43 C44 H44A 119.0 . . ? C44 C45 C46 123.1(12) . . ? C44 C45 H45A 118.4 . . ? C46 C45 H45A 118.4 . . ? C47 C46 C45 113.7(13) . . ? C47 C46 C49 121.4(11) . . ? C45 C46 C49 123.3(10) . . ? C46 C47 C48 125.0(12) . . ? C46 C47 H47A 117.5 . . ? C48 C47 H47A 117.5 . . ? C43 C48 C47 116.7(11) . . ? C43 C48 H48A 121.6 . . ? C47 C48 H48A 121.6 . . ? C22 C49 C46 102.0(9) . . ? C22 C49 C34 115.6(10) . . ? C46 C49 C34 112.7(10) . . ? C22 C49 C10 116.9(9) . . ? C46 C49 C10 109.3(9) . . ? C34 C49 C10 100.6(8) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.419 _refine_diff_density_min -0.431 _refine_diff_density_rms 0.095 # Attachment '- CCDC-822538.cif' data_cc22o _database_code_depnum_ccdc_archive 'CCDC 822539' #TrackingRef '- CCDC-822538.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C64.5 H77.5 Cl2 Cu N10.5 O6.5' _chemical_formula_weight 1238.31 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 orthorhombic _symmetry_space_group_name_H-M Pban loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x+1/2, y, -z' 'x, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x-1/2, -y, z' '-x, y-1/2, z' _cell_length_a 14.995(3) _cell_length_b 30.625(7) _cell_length_c 14.689(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6746(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 364 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 25.00 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2612 _exptl_absorpt_coefficient_mu 0.459 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7739 _exptl_absorpt_correction_T_max 0.8621 _exptl_absorpt_process_details sadabs _exptl_special_details ; Crystals were of poor quality and only weakly diffracting resulting in a relatively high value for Rint. Systematic absences were consistent with space group Pban and a only this space group gave a chemically reasonable solution. ; _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-I CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 60393 _diffrn_reflns_av_R_equivalents 0.1884 _diffrn_reflns_av_sigmaI/netI 0.1299 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5946 _reflns_number_gt 2853 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL XP' _computing_publication_material 'Bruker SHELXTL XCIF' loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.001 -0.003 -0.006 3787 1866 '' _platon_squeeze_details ; The unit cell contains an estimated 26 molecules of DMF which have been treated as a diffuse contribution to the overall scattering without specific atom positions by SQUEEZE/PLATON. 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. There was evidence of disorder at the Cu2-Cl2-N13 coordination envoronment. The largest residual peak is close to Cu2 and there is evidence for splitting peaks N13 - C18. All attempts to model this disorder with two sets of CuCl(py) fragments resulted in unstable refinement and/or NPD atoms. ; _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^)+(0.0914P)^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 5946 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1666 _refine_ls_R_factor_gt 0.0821 _refine_ls_wR_factor_ref 0.2162 _refine_ls_wR_factor_gt 0.1891 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 1.7500 0.7500 0.5000 0.0662(5) Uani 1 4 d S . . Cl1 Cl 1.7500 0.7500 0.6810(3) 0.1560(13) Uani 1 2 d S . . N1 N 1.8460(2) 0.79685(10) 0.5034(3) 0.0516(10) Uani 1 1 d . . . C2 C 1.9105(3) 0.79657(13) 0.4418(4) 0.0526(13) Uani 1 1 d . . . H2A H 1.9122 0.7735 0.3987 0.063 Uiso 1 1 calc R . . C3 C 1.9762(3) 0.82885(13) 0.4378(4) 0.0541(13) Uani 1 1 d . . . H3A H 2.0215 0.8280 0.3927 0.065 Uiso 1 1 calc R . . C4 C 1.9731(2) 0.86286(11) 0.5033(3) 0.0402(10) Uani 1 1 d . . . C5 C 1.9071(3) 0.86077(13) 0.5669(3) 0.0503(12) Uani 1 1 d . . . H5A H 1.9040 0.8821 0.6138 0.060 Uiso 1 1 calc R . . C6 C 1.8462(3) 0.82849(12) 0.5633(3) 0.0512(13) Uani 1 1 d . . . H6A H 1.8000 0.8287 0.6075 0.061 Uiso 1 1 calc R . . C7 C 2.0407(2) 0.89818(11) 0.5039(3) 0.0335(9) Uani 1 1 d . . . C8 C 2.0905(3) 0.90692(11) 0.4240(3) 0.0429(12) Uani 1 1 d . . . H8A H 2.0803 0.8898 0.3710 0.052 Uiso 1 1 calc R . . C9 C 2.1541(2) 0.94006(12) 0.4215(3) 0.0342(10) Uani 1 1 d . . . H9A H 2.1872 0.9452 0.3674 0.041 Uiso 1 1 calc R . . C10 C 2.1693(2) 0.96586(10) 0.4986(3) 0.0310(9) Uani 1 1 d . . . C11 C 2.1195(2) 0.95703(11) 0.5755(3) 0.0338(10) Uani 1 1 d . . . H11A H 2.1284 0.9740 0.6289 0.041 Uiso 1 1 calc R . . C12 C 2.0568(2) 0.92393(12) 0.5760(3) 0.0351(10) Uani 1 1 d . . . H12A H 2.0234 0.9192 0.6301 0.042 Uiso 1 1 calc R . . N13 N 2.2523(7) 1.20119(14) 0.0946(4) 0.151(4) Uani 1 1 d . . . C14 C 2.3236(7) 1.1930(2) 0.1477(5) 0.168(5) Uani 1 1 d . . . H14A H 2.3737 1.2120 0.1448 0.202 Uiso 1 1 calc R . . C15 C 2.3256(5) 1.1582(2) 0.2058(5) 0.125(3) Uani 1 1 d . . . H15A H 2.3770 1.1532 0.2421 0.150 Uiso 1 1 calc R . . C16 C 2.2543(5) 1.13032(14) 0.2123(3) 0.0820(18) Uani 1 1 d . . . C17 C 2.1797(6) 1.1381(2) 0.1579(5) 0.145(3) Uani 1 1 d . . . H17A H 2.1287 1.1197 0.1591 0.174 Uiso 1 1 calc R . . C18 C 2.1851(8) 1.1750(3) 0.1012(5) 0.171(5) Uani 1 1 d . . . H18A H 2.1347 1.1812 0.0642 0.205 Uiso 1 1 calc R . . C19 C 2.2598(4) 1.09281(12) 0.2806(3) 0.0504(12) Uani 1 1 d . . . C20 C 2.3302(3) 1.08657(13) 0.3384(3) 0.0515(13) Uani 1 1 d . . . H20A H 2.3823 1.1040 0.3321 0.062 Uiso 1 1 calc R . . C21 C 2.3262(3) 1.05527(12) 0.4055(3) 0.0421(11) Uani 1 1 d . . . H21A H 2.3752 1.0520 0.4460 0.050 Uiso 1 1 calc R . . C22 C 2.2526(3) 1.02839(10) 0.4154(3) 0.0324(9) Uani 1 1 d . . . C23 C 2.1820(3) 1.03398(11) 0.3567(3) 0.0361(10) Uani 1 1 d . . . H23A H 2.1308 1.0159 0.3630 0.043 Uiso 1 1 calc R . . C24 C 2.1837(3) 1.06531(13) 0.2887(3) 0.0516(12) Uani 1 1 d . . . H24A H 2.1348 1.0684 0.2480 0.062 Uiso 1 1 calc R . . C25 C 2.2500 0.99697(14) 0.5000 0.0301(12) Uani 1 2 d S . . Cu2 Cu 2.2500 1.2500 0.0000 0.244(2) Uani 1 4 d S . . Cl2 Cl 2.4565(3) 1.2500 0.0000 0.1709(14) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0238(6) 0.0172(5) 0.1576(13) 0.000 0.000 0.000 Cl1 0.126(2) 0.106(2) 0.236(4) 0.000 0.000 0.0031(18) N1 0.0293(19) 0.0228(18) 0.103(3) 0.009(2) 0.010(2) -0.0105(14) C2 0.029(2) 0.038(3) 0.091(4) -0.010(3) -0.004(3) -0.012(2) C3 0.039(3) 0.035(2) 0.089(4) -0.006(3) -0.011(3) -0.009(2) C4 0.038(2) 0.0138(18) 0.069(3) 0.003(2) -0.013(3) 0.0017(16) C5 0.035(2) 0.036(2) 0.080(3) -0.014(2) 0.030(3) -0.009(2) C6 0.047(3) 0.018(2) 0.088(4) -0.016(2) 0.016(3) -0.013(2) C7 0.029(2) 0.027(2) 0.045(2) 0.007(2) 0.008(2) -0.0011(16) C8 0.038(2) 0.016(2) 0.075(3) -0.013(2) -0.024(3) 0.0028(18) C9 0.030(2) 0.029(2) 0.043(3) 0.001(2) 0.009(2) 0.0069(18) C10 0.028(2) 0.0200(18) 0.044(2) -0.003(2) 0.006(2) -0.0020(15) C11 0.034(2) 0.025(2) 0.043(3) -0.0027(19) -0.008(2) 0.0057(18) C12 0.036(2) 0.028(2) 0.041(3) -0.003(2) 0.016(2) 0.0015(19) N13 0.386(12) 0.022(2) 0.045(3) -0.005(2) 0.043(5) -0.010(5) C14 0.326(13) 0.100(6) 0.078(5) 0.059(5) -0.029(7) -0.081(7) C15 0.168(7) 0.075(4) 0.134(6) 0.057(4) -0.045(5) -0.048(5) C16 0.168(6) 0.023(2) 0.055(3) 0.001(2) 0.033(4) 0.004(4) C17 0.215(8) 0.096(5) 0.123(6) 0.086(5) -0.036(6) 0.029(5) C18 0.295(13) 0.122(7) 0.094(6) 0.042(6) -0.020(7) 0.109(8) C19 0.090(4) 0.024(2) 0.038(2) -0.0008(18) 0.006(3) -0.002(3) C20 0.075(3) 0.029(2) 0.050(3) 0.008(2) 0.003(3) -0.019(2) C21 0.042(3) 0.027(2) 0.056(3) -0.002(2) 0.000(2) -0.019(2) C22 0.035(2) 0.0180(18) 0.044(2) 0.0016(16) 0.002(2) 0.013(2) C23 0.038(2) 0.021(2) 0.050(3) 0.0090(19) 0.006(2) 0.0046(18) C24 0.070(3) 0.036(3) 0.048(3) 0.006(2) -0.001(3) 0.013(2) C25 0.035(3) 0.017(2) 0.039(3) 0.000 0.005(3) 0.000 Cu2 0.683(6) 0.0195(7) 0.0285(7) 0.000 0.000 0.000 Cl2 0.279(4) 0.121(2) 0.113(2) 0.0089(19) 0.000 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 2.032(3) 2_865 ? Cu1 N1 2.032(3) 4_566 ? Cu1 N1 2.032(3) 3_856 ? Cu1 N1 2.032(3) . ? Cu1 Cl1 2.658(4) 3_856 ? Cu1 Cl1 2.658(4) . ? N1 C6 1.308(5) . ? N1 C2 1.325(5) . ? C2 C3 1.397(5) . ? C2 H2A 0.9500 . ? C3 C4 1.418(6) . ? C3 H3A 0.9500 . ? C4 C5 1.363(5) . ? C4 C7 1.483(5) . ? C5 C6 1.347(5) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C12 1.342(5) . ? C7 C8 1.417(5) . ? C8 C9 1.393(5) . ? C8 H8A 0.9500 . ? C9 C10 1.400(5) . ? C9 H9A 0.9500 . ? C10 C11 1.380(5) . ? C10 C25 1.540(4) . ? C11 C12 1.383(5) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? N13 C18 1.292(13) . ? N13 C14 1.347(12) . ? N13 Cu2 2.041(5) . ? C14 C15 1.367(8) . ? C14 H14A 0.9500 . ? C15 C16 1.371(8) . ? C15 H15A 0.9500 . ? C16 C17 1.395(9) . ? C16 C19 1.528(6) . ? C17 C18 1.406(9) . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C19 C20 1.367(6) . ? C19 C24 1.424(6) . ? C20 C21 1.376(5) . ? C20 H20A 0.9500 . ? C21 C22 1.385(5) . ? C21 H21A 0.9500 . ? C22 C23 1.377(5) . ? C22 C25 1.572(4) . ? C23 C24 1.386(5) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C25 C10 1.540(4) 3_956 ? C25 C22 1.572(4) 3_956 ? Cu2 N13 2.041(5) 3_955 ? Cu2 N13 2.041(5) 2_975 ? Cu2 N13 2.041(5) 4_575 ? 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 90.20(18) 2_865 4_566 ? N1 Cu1 N1 89.87(18) 2_865 3_856 ? N1 Cu1 N1 177.2(2) 4_566 3_856 ? N1 Cu1 N1 177.2(2) 2_865 . ? N1 Cu1 N1 89.87(18) 4_566 . ? N1 Cu1 N1 90.20(18) 3_856 . ? N1 Cu1 Cl1 91.41(12) 2_865 3_856 ? N1 Cu1 Cl1 88.59(12) 4_566 3_856 ? N1 Cu1 Cl1 88.59(12) 3_856 3_856 ? N1 Cu1 Cl1 91.41(12) . 3_856 ? N1 Cu1 Cl1 88.59(12) 2_865 . ? N1 Cu1 Cl1 91.41(12) 4_566 . ? N1 Cu1 Cl1 91.41(12) 3_856 . ? N1 Cu1 Cl1 88.59(12) . . ? Cl1 Cu1 Cl1 180.000(1) 3_856 . ? C6 N1 C2 117.5(3) . . ? C6 N1 Cu1 122.8(3) . . ? C2 N1 Cu1 119.7(3) . . ? N1 C2 C3 122.7(4) . . ? N1 C2 H2A 118.7 . . ? C3 C2 H2A 118.7 . . ? C2 C3 C4 117.9(4) . . ? C2 C3 H3A 121.0 . . ? C4 C3 H3A 121.0 . . ? C5 C4 C3 117.0(4) . . ? C5 C4 C7 121.8(4) . . ? C3 C4 C7 121.2(4) . . ? C6 C5 C4 120.0(4) . . ? C6 C5 H5A 120.0 . . ? C4 C5 H5A 120.0 . . ? N1 C6 C5 124.9(4) . . ? N1 C6 H6A 117.6 . . ? C5 C6 H6A 117.6 . . ? C12 C7 C8 116.6(3) . . ? C12 C7 C4 123.9(4) . . ? C8 C7 C4 119.5(4) . . ? C9 C8 C7 121.3(4) . . ? C9 C8 H8A 119.3 . . ? C7 C8 H8A 119.3 . . ? C8 C9 C10 120.1(4) . . ? C8 C9 H9A 120.0 . . ? C10 C9 H9A 120.0 . . ? C11 C10 C9 117.6(3) . . ? C11 C10 C25 122.4(3) . . ? C9 C10 C25 119.2(3) . . ? C10 C11 C12 121.1(4) . . ? C10 C11 H11A 119.5 . . ? C12 C11 H11A 119.5 . . ? C7 C12 C11 123.3(4) . . ? C7 C12 H12A 118.4 . . ? C11 C12 H12A 118.4 . . ? C18 N13 C14 117.4(6) . . ? C18 N13 Cu2 119.6(8) . . ? C14 N13 Cu2 122.9(7) . . ? N13 C14 C15 121.6(8) . . ? N13 C14 H14A 119.2 . . ? C15 C14 H14A 119.2 . . ? C14 C15 C16 120.8(7) . . ? C14 C15 H15A 119.6 . . ? C16 C15 H15A 119.6 . . ? C15 C16 C17 118.7(5) . . ? C15 C16 C19 118.1(6) . . ? C17 C16 C19 123.2(6) . . ? C16 C17 C18 115.5(8) . . ? C16 C17 H17A 122.3 . . ? C18 C17 H17A 122.3 . . ? N13 C18 C17 126.1(9) . . ? N13 C18 H18A 116.9 . . ? C17 C18 H18A 116.9 . . ? C20 C19 C24 119.0(4) . . ? C20 C19 C16 123.7(5) . . ? C24 C19 C16 117.1(5) . . ? C19 C20 C21 120.5(4) . . ? C19 C20 H20A 119.7 . . ? C21 C20 H20A 119.7 . . ? C20 C21 C22 121.6(4) . . ? C20 C21 H21A 119.2 . . ? C22 C21 H21A 119.2 . . ? C23 C22 C21 118.2(3) . . ? C23 C22 C25 123.5(3) . . ? C21 C22 C25 117.8(3) . . ? C22 C23 C24 121.6(4) . . ? C22 C23 H23A 119.2 . . ? C24 C23 H23A 119.2 . . ? C23 C24 C19 118.9(4) . . ? C23 C24 H24A 120.5 . . ? C19 C24 H24A 120.5 . . ? C10 C25 C10 103.6(4) . 3_956 ? C10 C25 C22 111.7(2) . 3_956 ? C10 C25 C22 112.8(2) 3_956 3_956 ? C10 C25 C22 112.8(2) . . ? C10 C25 C22 111.7(2) 3_956 . ? C22 C25 C22 104.5(4) 3_956 . ? N13 Cu2 N13 85.8(3) . 3_955 ? N13 Cu2 N13 94.2(3) . 2_975 ? N13 Cu2 N13 178.1(6) 3_955 2_975 ? N13 Cu2 N13 178.1(6) . 4_575 ? N13 Cu2 N13 94.2(3) 3_955 4_575 ? N13 Cu2 N13 85.8(3) 2_975 4_575 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.084 _refine_diff_density_min -0.935 _refine_diff_density_rms 0.071