# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_6 #TrackingRef '6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H13 Cl3 Cu N6 O10' _chemical_formula_weight 547.15 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 Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.8122(10) _cell_length_b 11.1482(11) _cell_length_c 31.445(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3790.3(6) _cell_formula_units_Z 8 _cell_measurement_temperature 248(2) _cell_measurement_reflns_used 5340 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 25.89 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.918 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2200 _exptl_absorpt_coefficient_mu 1.642 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7039 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 248(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25525 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4705 _reflns_number_gt 3753 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0488P)^2^+3.3961P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4705 _refine_ls_number_parameters 285 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.1004 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.014 _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 C1 C 1.1029(3) 1.1583(2) 0.64570(9) 0.0363(6) Uani 1 1 d . . . C2 C 1.1534(3) 1.1239(3) 0.68479(8) 0.0392(6) Uani 1 1 d . . . H2 H 1.1951 1.1795 0.7021 0.047 Uiso 1 1 calc R . . C3 C 1.1404(3) 1.0082(2) 0.69683(8) 0.0375(6) Uani 1 1 d . . . H3 H 1.1750 0.9792 0.7223 0.045 Uiso 1 1 calc R . . C4 C 1.0728(2) 0.9335(2) 0.66953(7) 0.0289(5) Uani 1 1 d . . . C5 C 0.9448(2) 0.6483(2) 0.65270(8) 0.0266(5) Uani 1 1 d . . . C6 C 0.9830(3) 0.5643(2) 0.68693(9) 0.0398(6) Uani 1 1 d . . . H6A H 0.9162 0.5556 0.7073 0.060 Uiso 1 1 calc R . . H6B H 1.0557 0.5956 0.7012 0.060 Uiso 1 1 calc R . . H6C H 1.0022 0.4866 0.6746 0.060 Uiso 1 1 calc R . . C7 C 0.8588(2) 0.6148(2) 0.61827(7) 0.0245(4) Uani 1 1 d . . . C8 C 0.7971(2) 0.5066(2) 0.61668(8) 0.0283(5) Uani 1 1 d . . . H8 H 0.8157 0.4471 0.6369 0.034 Uiso 1 1 calc R . . C9 C 0.6908(2) 0.5678(2) 0.55771(8) 0.0331(5) Uani 1 1 d . . . H9 H 0.6324 0.5534 0.5362 0.040 Uiso 1 1 calc R . . C10 C 0.7545(2) 0.6763(2) 0.55834(7) 0.0326(5) Uani 1 1 d . . . H10 H 0.7399 0.7332 0.5369 0.039 Uiso 1 1 calc R . . Cl1 Cl 1.12431(9) 1.30296(6) 0.62821(3) 0.0526(2) Uani 1 1 d . . . Cl2 Cl 0.17530(6) 0.73434(6) 0.78798(2) 0.03906(16) Uani 1 1 d . . . Cl3 Cl 0.32906(6) 0.05652(6) 0.55472(2) 0.04189(17) Uani 1 1 d . . . Cu1 Cu 0.92658(3) 0.85487(3) 0.600874(9) 0.02749(10) Uani 1 1 d . . . H2W H 0.916(2) 0.759(3) 0.4653(12) 0.065(12) Uiso 1 1 d D . . H3W H 0.984(5) 0.6620(18) 0.4794(17) 0.11(2) Uiso 1 1 d D . . H4W H 1.0871(17) 0.893(3) 0.5462(10) 0.045(10) Uiso 1 1 d D . . N1 N 1.0406(2) 1.08842(19) 0.62052(7) 0.0369(5) Uani 1 1 d . . . N2 N 1.0251(2) 0.97370(18) 0.63318(6) 0.0305(4) Uani 1 1 d . . . N3 N 1.05386(19) 0.81424(19) 0.67811(7) 0.0330(5) Uani 1 1 d . . . H3A H 1.0868 0.7778 0.6998 0.040 Uiso 1 1 calc R . . N4 N 0.97855(18) 0.75809(17) 0.64948(6) 0.0265(4) Uani 1 1 d . . . N5 N 0.83549(18) 0.70055(17) 0.58881(6) 0.0258(4) Uani 1 1 d . . . N6 N 0.71131(18) 0.48434(17) 0.58702(6) 0.0277(4) Uani 1 1 d . . . O1 O 0.9814(3) 0.7358(2) 0.47820(8) 0.0602(6) Uani 1 1 d D . . O2 O 0.2737(3) 0.1540(3) 0.53408(11) 0.0975(11) Uani 1 1 d . . . O3 O 0.3287(3) 0.0716(3) 0.59932(9) 0.0962(11) Uani 1 1 d . . . O4 O 0.2629(3) -0.0509(3) 0.54563(11) 0.0862(9) Uani 1 1 d . . . O5 O 0.4542(2) 0.0393(3) 0.54215(10) 0.0797(8) Uani 1 1 d . . . O6 O 0.0643(2) 0.7767(2) 0.76736(7) 0.0595(6) Uani 1 1 d . . . O7 O 0.2791(3) 0.7937(3) 0.76994(9) 0.0825(9) Uani 1 1 d . . . O8 O 0.1674(2) 0.7599(2) 0.83228(6) 0.0551(6) Uani 1 1 d . . . O9 O 0.1868(3) 0.6094(2) 0.78164(10) 0.0840(9) Uani 1 1 d . . . O10 O 1.01547(18) 0.87857(18) 0.54410(6) 0.0377(4) Uani 1 1 d D . . H1W H 0.9962 0.8236 0.5276 0.057 Uiso 1 1 calc RD . . 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 C1 0.0441(15) 0.0265(12) 0.0383(14) -0.0014(10) 0.0021(11) -0.0060(11) C2 0.0474(16) 0.0369(14) 0.0334(13) -0.0078(11) -0.0046(11) -0.0099(12) C3 0.0472(15) 0.0373(14) 0.0279(12) -0.0024(10) -0.0068(11) -0.0060(12) C4 0.0309(12) 0.0289(12) 0.0267(11) -0.0010(9) 0.0004(9) -0.0008(10) C5 0.0280(11) 0.0246(11) 0.0273(11) 0.0018(9) -0.0013(9) 0.0016(9) C6 0.0501(16) 0.0303(13) 0.0390(14) 0.0095(11) -0.0128(12) -0.0018(12) C7 0.0263(11) 0.0229(11) 0.0242(11) 0.0008(8) 0.0016(8) 0.0014(9) C8 0.0321(12) 0.0241(11) 0.0286(11) 0.0047(9) -0.0018(9) 0.0005(10) C9 0.0373(13) 0.0322(13) 0.0299(12) 0.0054(10) -0.0069(10) -0.0087(11) C10 0.0422(14) 0.0294(12) 0.0263(11) 0.0076(9) -0.0068(10) -0.0071(11) Cl1 0.0761(5) 0.0286(3) 0.0531(4) 0.0020(3) -0.0061(4) -0.0150(3) Cl2 0.0463(4) 0.0410(4) 0.0298(3) -0.0052(2) -0.0028(3) 0.0060(3) Cl3 0.0398(3) 0.0398(4) 0.0461(4) 0.0019(3) 0.0012(3) -0.0031(3) Cu1 0.03573(17) 0.02182(15) 0.02491(15) 0.00248(10) -0.00483(11) -0.00385(12) N1 0.0509(13) 0.0253(11) 0.0345(11) 0.0008(8) -0.0067(10) -0.0063(10) N2 0.0389(11) 0.0249(10) 0.0277(10) 0.0004(8) -0.0042(9) -0.0032(9) N3 0.0396(12) 0.0294(10) 0.0300(10) 0.0021(8) -0.0117(9) -0.0032(9) N4 0.0277(9) 0.0254(10) 0.0265(9) 0.0007(7) -0.0039(8) -0.0002(8) N5 0.0286(10) 0.0234(9) 0.0253(9) 0.0027(7) 0.0000(8) -0.0010(8) N6 0.0304(10) 0.0248(10) 0.0278(10) 0.0020(8) 0.0007(8) -0.0026(8) O1 0.0762(18) 0.0532(15) 0.0511(14) -0.0089(11) -0.0162(12) -0.0048(14) O2 0.099(2) 0.079(2) 0.115(3) 0.0474(19) -0.003(2) 0.0213(18) O3 0.098(2) 0.132(3) 0.0582(17) -0.0279(17) -0.0064(15) 0.029(2) O4 0.0625(16) 0.0639(18) 0.132(3) 0.0012(17) -0.0211(17) -0.0228(14) O5 0.0480(14) 0.086(2) 0.105(2) -0.0019(17) 0.0175(14) -0.0039(14) O6 0.0620(14) 0.0764(17) 0.0402(12) 0.0038(11) -0.0175(10) 0.0129(12) O7 0.0653(17) 0.106(2) 0.0764(18) 0.0061(17) 0.0134(14) -0.0184(16) O8 0.0677(15) 0.0688(15) 0.0286(10) -0.0077(9) -0.0076(10) 0.0142(12) O9 0.113(2) 0.0457(14) 0.093(2) -0.0230(14) -0.0099(18) 0.0210(15) O10 0.0377(11) 0.0424(11) 0.0330(9) -0.0047(8) 0.0085(8) -0.0087(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 C1 N1 1.299(3) . ? C1 C2 1.398(4) . ? C1 Cl1 1.720(3) . ? C2 C3 1.352(4) . ? C2 H2 0.9400 . ? C3 C4 1.401(3) . ? C3 H3 0.9400 . ? C4 N2 1.332(3) . ? C4 N3 1.372(3) . ? C5 N4 1.281(3) . ? C5 C7 1.475(3) . ? C5 C6 1.486(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 H6C 0.9700 . ? C7 N5 1.355(3) . ? C7 C8 1.379(3) . ? C8 N6 1.339(3) . ? C8 H8 0.9400 . ? C9 N6 1.328(3) . ? C9 C10 1.392(3) . ? C9 H9 0.9400 . ? C10 N5 1.326(3) . ? C10 H10 0.9400 . ? Cl2 O9 1.412(3) . ? Cl2 O7 1.421(3) . ? Cl2 O8 1.424(2) . ? Cl2 O6 1.444(2) . ? Cl3 O2 1.400(3) . ? Cl3 O3 1.412(3) . ? Cl3 O5 1.422(3) . ? Cl3 O4 1.424(3) . ? Cu1 N4 1.9534(19) . ? Cu1 N2 1.980(2) . ? Cu1 N5 2.018(2) . ? Cu1 O10 2.0446(18) . ? Cu1 N6 2.1204(19) 8_765 ? N1 N2 1.350(3) . ? N3 N4 1.366(3) . ? N3 H3A 0.8700 . ? N6 Cu1 2.1204(19) 8_755 ? O1 H2W 0.857(18) . ? O1 H3W 0.824(19) . ? O10 H4W 0.793(17) . ? O10 H1W 0.8300 . ? 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 C1 C2 125.0(2) . . ? N1 C1 Cl1 115.9(2) . . ? C2 C1 Cl1 119.0(2) . . ? C3 C2 C1 117.8(2) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C2 C3 C4 116.7(2) . . ? C2 C3 H3 121.6 . . ? C4 C3 H3 121.6 . . ? N2 C4 N3 115.9(2) . . ? N2 C4 C3 121.9(2) . . ? N3 C4 C3 122.2(2) . . ? N4 C5 C7 111.3(2) . . ? N4 C5 C6 125.5(2) . . ? C7 C5 C6 123.2(2) . . ? 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 . . ? N5 C7 C8 120.2(2) . . ? N5 C7 C5 116.1(2) . . ? C8 C7 C5 123.6(2) . . ? N6 C8 C7 121.5(2) . . ? N6 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? N6 C9 C10 121.1(2) . . ? N6 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? N5 C10 C9 120.9(2) . . ? N5 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? O9 Cl2 O7 109.5(2) . . ? O9 Cl2 O8 109.91(17) . . ? O7 Cl2 O8 110.16(17) . . ? O9 Cl2 O6 109.40(17) . . ? O7 Cl2 O6 108.99(17) . . ? O8 Cl2 O6 108.90(14) . . ? O2 Cl3 O3 111.5(2) . . ? O2 Cl3 O5 112.5(2) . . ? O3 Cl3 O5 107.1(2) . . ? O2 Cl3 O4 110.2(2) . . ? O3 Cl3 O4 107.3(2) . . ? O5 Cl3 O4 107.97(19) . . ? N4 Cu1 N2 79.25(8) . . ? N4 Cu1 N5 79.44(8) . . ? N2 Cu1 N5 158.30(8) . . ? N4 Cu1 O10 128.27(9) . . ? N2 Cu1 O10 96.24(8) . . ? N5 Cu1 O10 100.10(8) . . ? N4 Cu1 N6 137.64(8) . 8_765 ? N2 Cu1 N6 91.61(8) . 8_765 ? N5 Cu1 N6 101.45(8) . 8_765 ? O10 Cu1 N6 93.62(8) . 8_765 ? C1 N1 N2 116.9(2) . . ? C4 N2 N1 121.6(2) . . ? C4 N2 Cu1 115.07(16) . . ? N1 N2 Cu1 123.34(16) . . ? N4 N3 C4 113.80(19) . . ? N4 N3 H3A 123.1 . . ? C4 N3 H3A 123.1 . . ? C5 N4 N3 123.7(2) . . ? C5 N4 Cu1 120.50(16) . . ? N3 N4 Cu1 115.73(15) . . ? C10 N5 C7 118.2(2) . . ? C10 N5 Cu1 129.17(16) . . ? C7 N5 Cu1 112.48(15) . . ? C9 N6 C8 118.0(2) . . ? C9 N6 Cu1 120.16(16) . 8_755 ? C8 N6 Cu1 118.05(15) . 8_755 ? H2W O1 H3W 111(4) . . ? Cu1 O10 H4W 114(2) . . ? Cu1 O10 H1W 109.5 . . ? H4W O10 H1W 116.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 2.4(5) . . . . ? Cl1 C1 C2 C3 -176.9(2) . . . . ? C1 C2 C3 C4 -2.4(4) . . . . ? C2 C3 C4 N2 0.9(4) . . . . ? C2 C3 C4 N3 179.6(2) . . . . ? N4 C5 C7 N5 3.1(3) . . . . ? C6 C5 C7 N5 -178.4(2) . . . . ? N4 C5 C7 C8 -172.4(2) . . . . ? C6 C5 C7 C8 6.2(4) . . . . ? N5 C7 C8 N6 -1.6(4) . . . . ? C5 C7 C8 N6 173.7(2) . . . . ? N6 C9 C10 N5 -1.5(4) . . . . ? C2 C1 N1 N2 -0.7(4) . . . . ? Cl1 C1 N1 N2 178.57(19) . . . . ? N3 C4 N2 N1 -178.0(2) . . . . ? C3 C4 N2 N1 0.8(4) . . . . ? N3 C4 N2 Cu1 4.0(3) . . . . ? C3 C4 N2 Cu1 -177.3(2) . . . . ? C1 N1 N2 C4 -0.9(4) . . . . ? C1 N1 N2 Cu1 177.0(2) . . . . ? N4 Cu1 N2 C4 -1.01(18) . . . . ? N5 Cu1 N2 C4 9.9(4) . . . . ? O10 Cu1 N2 C4 -128.84(18) . . . . ? N6 Cu1 N2 C4 137.34(18) 8_765 . . . ? N4 Cu1 N2 N1 -179.0(2) . . . . ? N5 Cu1 N2 N1 -168.1(2) . . . . ? O10 Cu1 N2 N1 53.2(2) . . . . ? N6 Cu1 N2 N1 -40.7(2) 8_765 . . . ? N2 C4 N3 N4 -5.7(3) . . . . ? C3 C4 N3 N4 175.6(2) . . . . ? C7 C5 N4 N3 177.2(2) . . . . ? C6 C5 N4 N3 -1.3(4) . . . . ? C7 C5 N4 Cu1 -4.6(3) . . . . ? C6 C5 N4 Cu1 176.9(2) . . . . ? C4 N3 N4 C5 -176.9(2) . . . . ? C4 N3 N4 Cu1 4.8(3) . . . . ? N2 Cu1 N4 C5 179.5(2) . . . . ? N5 Cu1 N4 C5 3.59(19) . . . . ? O10 Cu1 N4 C5 -91.0(2) . . . . ? N6 Cu1 N4 C5 99.0(2) 8_765 . . . ? N2 Cu1 N4 N3 -2.14(16) . . . . ? N5 Cu1 N4 N3 -178.06(18) . . . . ? O10 Cu1 N4 N3 87.35(18) . . . . ? N6 Cu1 N4 N3 -82.6(2) 8_765 . . . ? C9 C10 N5 C7 2.9(4) . . . . ? C9 C10 N5 Cu1 -173.04(19) . . . . ? C8 C7 N5 C10 -1.4(3) . . . . ? C5 C7 N5 C10 -177.0(2) . . . . ? C8 C7 N5 Cu1 175.22(17) . . . . ? C5 C7 N5 Cu1 -0.4(2) . . . . ? N4 Cu1 N5 C10 174.7(2) . . . . ? N2 Cu1 N5 C10 163.8(2) . . . . ? O10 Cu1 N5 C10 -57.9(2) . . . . ? N6 Cu1 N5 C10 37.9(2) 8_765 . . . ? N4 Cu1 N5 C7 -1.43(16) . . . . ? N2 Cu1 N5 C7 -12.3(3) . . . . ? O10 Cu1 N5 C7 125.92(16) . . . . ? N6 Cu1 N5 C7 -138.25(16) 8_765 . . . ? C10 C9 N6 C8 -1.5(4) . . . . ? C10 C9 N6 Cu1 156.1(2) . . . 8_755 ? C7 C8 N6 C9 3.0(4) . . . . ? C7 C8 N6 Cu1 -155.04(18) . . . 8_755 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.608 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 878697' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_8 #TrackingRef '8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H15 Cl Cu N8 O9' _chemical_formula_weight 490.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M '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 32.804(3) _cell_length_b 6.6637(6) _cell_length_c 21.391(2) _cell_angle_alpha 90.00 _cell_angle_beta 128.802(5) _cell_angle_gamma 90.00 _cell_volume 3644.1(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3878 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 27.27 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.787 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1992 _exptl_absorpt_coefficient_mu 1.412 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7843 _exptl_absorpt_correction_T_max 0.8353 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9586 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3199 _reflns_number_gt 2803 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0595P)^2^+8.8755P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3199 _refine_ls_number_parameters 281 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.1085 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.039 _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 O9 O 0.65108(17) 0.5534(5) 0.7317(2) 0.0914(11) Uani 1 1 d . . . Cu1 Cu 0.662808(14) 0.18888(6) 0.70291(2) 0.03990(16) Uani 1 1 d . . . Cl1 Cl 0.59737(4) 0.37766(17) 0.40104(6) 0.0610(3) Uani 1 1 d . . . N5 N 0.69356(10) 0.1074(4) 0.81619(15) 0.0408(6) Uani 1 1 d . . . C5 C 0.60189(13) 0.1206(5) 0.7523(2) 0.0459(8) Uani 1 1 d . . . N4 N 0.59876(10) 0.1578(4) 0.69030(16) 0.0396(6) Uani 1 1 d . . . N3 N 0.55366(10) 0.1955(5) 0.61555(17) 0.0458(7) Uani 1 1 d . . . H13 H 0.5234 0.1883 0.6038 0.055 Uiso 1 1 calc R . . N1 N 0.60943(10) 0.2572(4) 0.58746(16) 0.0390(6) Uani 1 1 d . . . N2 N 0.62087(11) 0.2999(4) 0.53828(16) 0.0422(6) Uani 1 1 d . . . C3 C 0.51767(13) 0.2825(5) 0.4793(2) 0.0457(8) Uani 1 1 d . . . H3 H 0.4834 0.2770 0.4608 0.055 Uiso 1 1 calc R . . O4 O 0.67476(10) -0.1413(4) 0.67416(14) 0.0500(6) Uani 1 1 d D . . H2W H 0.6672 -0.1430 0.6296 0.075 Uiso 1 1 calc RD . . O5 O 0.72255(9) 0.2703(4) 0.71169(15) 0.0524(6) Uani 1 1 d D . . H4W H 0.7221 0.2125 0.6774 0.079 Uiso 1 1 calc RD . . C2 C 0.52861(14) 0.3259(5) 0.4294(2) 0.0481(8) Uani 1 1 d . . . H2 H 0.5021 0.3514 0.3752 0.058 Uiso 1 1 calc R . . C1 C 0.58155(14) 0.3308(5) 0.4627(2) 0.0439(8) Uani 1 1 d . . . C7 C 0.65643(13) 0.0874(5) 0.82516(19) 0.0421(7) Uani 1 1 d . . . C4 C 0.56023(12) 0.2461(5) 0.56020(19) 0.0388(7) Uani 1 1 d . . . C8 C 0.66996(15) 0.0397(6) 0.8985(2) 0.0536(9) Uani 1 1 d . . . H8 H 0.6437 0.0297 0.9031 0.064 Uiso 1 1 calc R . . N6 N 0.71931(13) 0.0074(5) 0.96327(18) 0.0613(8) Uani 1 1 d . . . C9 C 0.75499(16) 0.0232(7) 0.9534(2) 0.0604(10) Uani 1 1 d . . . H9 H 0.7898 -0.0012 0.9971 0.072 Uiso 1 1 calc R . . C10 C 0.74303(13) 0.0747(6) 0.8806(2) 0.0499(8) Uani 1 1 d . . . H10 H 0.7697 0.0865 0.8768 0.060 Uiso 1 1 calc R . . N8 N 0.91439(12) 0.3277(5) 0.02671(19) 0.0531(8) Uani 1 1 d . . . O2 O 0.92987(19) 0.2926(7) -0.0105(3) 0.1197(16) Uani 1 1 d . . . O1 O 0.86798(11) 0.3340(5) -0.0087(2) 0.0798(10) Uani 1 1 d . . . O3 O 0.9467(2) 0.3555(10) 0.0963(2) 0.176(3) Uani 1 1 d . . . N7 N 0.62923(15) 0.5925(5) 0.7620(2) 0.0623(8) Uani 1 1 d . . . O7 O 0.58809(17) 0.6535(10) 0.7284(4) 0.182(3) Uani 1 1 d . . . C6 C 0.55710(16) 0.1129(9) 0.7537(3) 0.0744(13) Uani 1 1 d . . . H6A H 0.5279 0.1840 0.7082 0.112 Uiso 1 1 calc R . . H6B H 0.5671 0.1742 0.8021 0.112 Uiso 1 1 calc R . . H6C H 0.5475 -0.0243 0.7517 0.112 Uiso 1 1 calc R . . O10 O 0.73754(13) 0.0619(6) 0.6225(2) 0.0763(9) Uani 1 1 d D . . H1W H 0.666(2) -0.212(7) 0.695(2) 0.10(2) Uiso 1 1 d D . . H3W H 0.7471(11) 0.308(7) 0.7563(13) 0.080(16) Uiso 1 1 d D . . H5W H 0.7128(13) 0.071(11) 0.5755(11) 0.14(3) Uiso 1 1 d D . . H6W H 0.7686(5) 0.047(8) 0.648(2) 0.086(17) Uiso 1 1 d D . . O8 O 0.65694(19) 0.5589(7) 0.8341(2) 0.1130(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O9 0.151(3) 0.063(2) 0.113(3) -0.0147(19) 0.108(3) -0.021(2) Cu1 0.0311(2) 0.0515(3) 0.0365(2) 0.00262(16) 0.02087(19) -0.00017(16) Cl1 0.0676(6) 0.0768(7) 0.0504(5) 0.0064(5) 0.0427(5) 0.0030(5) N5 0.0399(14) 0.0424(15) 0.0389(14) -0.0015(12) 0.0241(12) 0.0007(12) C5 0.0440(18) 0.051(2) 0.0483(19) 0.0019(16) 0.0318(16) -0.0031(15) N4 0.0346(13) 0.0451(15) 0.0391(14) 0.0003(11) 0.0231(12) -0.0014(11) N3 0.0306(13) 0.0631(19) 0.0442(15) 0.0037(13) 0.0237(13) 0.0004(12) N1 0.0359(14) 0.0430(15) 0.0392(14) 0.0013(11) 0.0240(12) 0.0024(11) N2 0.0421(15) 0.0456(16) 0.0416(15) 0.0022(12) 0.0275(13) 0.0035(12) C3 0.0351(16) 0.052(2) 0.0435(18) 0.0001(15) 0.0214(15) 0.0035(14) O4 0.0480(14) 0.0513(15) 0.0405(13) 0.0010(11) 0.0228(12) 0.0014(11) O5 0.0387(13) 0.0756(18) 0.0458(14) -0.0143(13) 0.0279(12) -0.0145(12) C2 0.0429(18) 0.053(2) 0.0386(17) 0.0022(15) 0.0209(15) 0.0051(15) C1 0.0492(19) 0.0446(19) 0.0428(18) -0.0004(14) 0.0311(16) 0.0029(15) C7 0.0457(17) 0.0415(18) 0.0414(17) -0.0007(14) 0.0283(15) -0.0026(14) C4 0.0372(16) 0.0371(16) 0.0414(17) -0.0008(13) 0.0244(14) 0.0014(13) C8 0.055(2) 0.064(2) 0.0459(19) 0.0005(17) 0.0340(18) -0.0029(18) N6 0.064(2) 0.073(2) 0.0438(17) 0.0061(16) 0.0324(16) 0.0049(17) C9 0.055(2) 0.068(3) 0.043(2) 0.0035(18) 0.0236(18) 0.0093(19) C10 0.0432(18) 0.056(2) 0.0451(19) -0.0005(16) 0.0252(16) 0.0044(16) N8 0.0446(17) 0.0553(19) 0.0470(18) 0.0101(14) 0.0227(15) -0.0016(14) O2 0.132(3) 0.118(3) 0.189(5) 0.025(3) 0.139(4) 0.031(3) O1 0.0513(17) 0.094(2) 0.104(2) 0.0192(19) 0.0532(18) 0.0123(15) O3 0.163(5) 0.198(6) 0.041(2) 0.009(3) 0.002(2) -0.095(4) N7 0.068(2) 0.0498(19) 0.073(2) -0.0088(17) 0.046(2) -0.0041(17) O7 0.060(3) 0.188(6) 0.184(6) -0.046(4) 0.021(3) 0.039(3) C6 0.052(2) 0.119(4) 0.064(3) 0.015(3) 0.042(2) 0.002(2) O10 0.0548(18) 0.112(3) 0.0562(19) -0.0206(19) 0.0317(16) -0.0002(19) O8 0.140(4) 0.132(4) 0.084(3) 0.007(2) 0.078(3) 0.033(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 O9 N7 1.259(5) . ? O9 Cu1 2.593(3) . ? Cu1 O5 1.926(2) . ? Cu1 N4 1.954(3) . ? Cu1 N1 1.988(3) . ? Cu1 N5 2.030(3) . ? Cu1 O4 2.382(3) . ? Cl1 C1 1.721(3) . ? N5 C10 1.333(4) . ? N5 C7 1.353(4) . ? C5 N4 1.289(4) . ? C5 C7 1.478(5) . ? C5 C6 1.489(5) . ? N4 N3 1.358(4) . ? N3 C4 1.372(4) . ? N3 H13 0.8600 . ? N1 C4 1.331(4) . ? N1 N2 1.350(4) . ? N2 C1 1.307(4) . ? C3 C2 1.353(5) . ? C3 C4 1.406(5) . ? C3 H3 0.9300 . ? O4 H2W 0.8200 . ? O4 H1W 0.806(10) . ? O5 H4W 0.8200 . ? O5 H3W 0.811(10) . ? C2 C1 1.405(5) . ? C2 H2 0.9300 . ? C7 C8 1.373(5) . ? C8 N6 1.333(5) . ? C8 H8 0.9300 . ? N6 C9 1.317(5) . ? C9 C10 1.390(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? N8 O3 1.181(5) . ? N8 O1 1.203(4) . ? N8 O2 1.205(5) . ? N7 O7 1.135(5) . ? N7 O8 1.223(5) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? O10 H5W 0.806(10) . ? O10 H6W 0.804(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N7 O9 Cu1 122.3(2) . . ? O5 Cu1 N4 169.59(12) . . ? O5 Cu1 N1 96.14(11) . . ? N4 Cu1 N1 79.57(11) . . ? O5 Cu1 N5 104.17(11) . . ? N4 Cu1 N5 79.83(11) . . ? N1 Cu1 N5 159.41(11) . . ? O5 Cu1 O4 87.90(11) . . ? N4 Cu1 O4 101.72(10) . . ? N1 Cu1 O4 92.87(10) . . ? N5 Cu1 O4 91.26(10) . . ? O5 Cu1 O9 90.37(12) . . ? N4 Cu1 O9 79.93(12) . . ? N1 Cu1 O9 86.23(12) . . ? N5 Cu1 O9 90.22(11) . . ? O4 Cu1 O9 177.95(10) . . ? C10 N5 C7 117.3(3) . . ? C10 N5 Cu1 130.5(2) . . ? C7 N5 Cu1 112.2(2) . . ? N4 C5 C7 112.1(3) . . ? N4 C5 C6 125.7(3) . . ? C7 C5 C6 122.1(3) . . ? C5 N4 N3 124.9(3) . . ? C5 N4 Cu1 119.5(2) . . ? N3 N4 Cu1 115.3(2) . . ? N4 N3 C4 114.7(3) . . ? N4 N3 H13 122.7 . . ? C4 N3 H13 122.7 . . ? C4 N1 N2 121.5(3) . . ? C4 N1 Cu1 114.4(2) . . ? N2 N1 Cu1 123.9(2) . . ? C1 N2 N1 117.2(3) . . ? C2 C3 C4 117.3(3) . . ? C2 C3 H3 121.4 . . ? C4 C3 H3 121.4 . . ? Cu1 O4 H2W 109.5 . . ? Cu1 O4 H1W 103(4) . . ? H2W O4 H1W 132.0 . . ? Cu1 O5 H4W 109.5 . . ? Cu1 O5 H3W 114(3) . . ? H4W O5 H3W 130.1 . . ? C3 C2 C1 117.4(3) . . ? C3 C2 H2 121.3 . . ? C1 C2 H2 121.3 . . ? N2 C1 C2 124.8(3) . . ? N2 C1 Cl1 116.0(3) . . ? C2 C1 Cl1 119.1(3) . . ? N5 C7 C8 120.6(3) . . ? N5 C7 C5 116.0(3) . . ? C8 C7 C5 123.4(3) . . ? N1 C4 N3 116.0(3) . . ? N1 C4 C3 121.7(3) . . ? N3 C4 C3 122.2(3) . . ? N6 C8 C7 122.5(3) . . ? N6 C8 H8 118.7 . . ? C7 C8 H8 118.7 . . ? C9 N6 C8 116.3(3) . . ? N6 C9 C10 123.0(3) . . ? N6 C9 H9 118.5 . . ? C10 C9 H9 118.5 . . ? N5 C10 C9 120.3(3) . . ? N5 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? O3 N8 O1 124.8(5) . . ? O3 N8 O2 116.5(5) . . ? O1 N8 O2 118.7(4) . . ? O7 N7 O8 120.9(5) . . ? O7 N7 O9 125.6(6) . . ? O8 N7 O9 113.4(4) . . ? 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 . . ? H5W O10 H6W 136(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 N7 O9 Cu1 O5 -154.1(4) . . . . ? N7 O9 Cu1 N4 29.7(4) . . . . ? N7 O9 Cu1 N1 109.7(4) . . . . ? N7 O9 Cu1 N5 -50.0(4) . . . . ? N7 O9 Cu1 O4 174(3) . . . . ? O5 Cu1 N5 C10 -12.5(3) . . . . ? N4 Cu1 N5 C10 177.3(3) . . . . ? N1 Cu1 N5 C10 177.2(3) . . . . ? O4 Cu1 N5 C10 75.6(3) . . . . ? O9 Cu1 N5 C10 -103.0(3) . . . . ? O5 Cu1 N5 C7 166.5(2) . . . . ? N4 Cu1 N5 C7 -3.7(2) . . . . ? N1 Cu1 N5 C7 -3.8(5) . . . . ? O4 Cu1 N5 C7 -105.4(2) . . . . ? O9 Cu1 N5 C7 76.0(2) . . . . ? C7 C5 N4 N3 -179.5(3) . . . . ? C6 C5 N4 N3 -0.3(6) . . . . ? C7 C5 N4 Cu1 -5.6(4) . . . . ? C6 C5 N4 Cu1 173.6(4) . . . . ? O5 Cu1 N4 C5 -108.2(6) . . . . ? N1 Cu1 N4 C5 -174.6(3) . . . . ? N5 Cu1 N4 C5 5.4(3) . . . . ? O4 Cu1 N4 C5 94.6(3) . . . . ? O9 Cu1 N4 C5 -86.7(3) . . . . ? O5 Cu1 N4 N3 66.3(7) . . . . ? N1 Cu1 N4 N3 -0.1(2) . . . . ? N5 Cu1 N4 N3 179.9(2) . . . . ? O4 Cu1 N4 N3 -90.9(2) . . . . ? O9 Cu1 N4 N3 87.8(2) . . . . ? C5 N4 N3 C4 175.3(3) . . . . ? Cu1 N4 N3 C4 1.1(4) . . . . ? O5 Cu1 N1 C4 -171.3(2) . . . . ? N4 Cu1 N1 C4 -0.9(2) . . . . ? N5 Cu1 N1 C4 -0.8(5) . . . . ? O4 Cu1 N1 C4 100.5(2) . . . . ? O9 Cu1 N1 C4 -81.4(2) . . . . ? O5 Cu1 N1 N2 12.5(3) . . . . ? N4 Cu1 N1 N2 -177.1(3) . . . . ? N5 Cu1 N1 N2 -177.0(3) . . . . ? O4 Cu1 N1 N2 -75.7(3) . . . . ? O9 Cu1 N1 N2 102.5(3) . . . . ? C4 N1 N2 C1 0.2(4) . . . . ? Cu1 N1 N2 C1 176.1(2) . . . . ? C4 C3 C2 C1 0.0(5) . . . . ? N1 N2 C1 C2 1.1(5) . . . . ? N1 N2 C1 Cl1 -178.2(2) . . . . ? C3 C2 C1 N2 -1.2(5) . . . . ? C3 C2 C1 Cl1 178.0(3) . . . . ? C10 N5 C7 C8 1.4(5) . . . . ? Cu1 N5 C7 C8 -177.7(3) . . . . ? C10 N5 C7 C5 -178.8(3) . . . . ? Cu1 N5 C7 C5 2.0(4) . . . . ? N4 C5 C7 N5 2.1(5) . . . . ? C6 C5 C7 N5 -177.2(4) . . . . ? N4 C5 C7 C8 -178.2(3) . . . . ? C6 C5 C7 C8 2.6(6) . . . . ? N2 N1 C4 N3 178.1(3) . . . . ? Cu1 N1 C4 N3 1.8(4) . . . . ? N2 N1 C4 C3 -1.4(5) . . . . ? Cu1 N1 C4 C3 -177.6(3) . . . . ? N4 N3 C4 N1 -1.9(4) . . . . ? N4 N3 C4 C3 177.5(3) . . . . ? C2 C3 C4 N1 1.2(5) . . . . ? C2 C3 C4 N3 -178.2(3) . . . . ? N5 C7 C8 N6 -1.3(6) . . . . ? C5 C7 C8 N6 179.0(4) . . . . ? C7 C8 N6 C9 -0.1(6) . . . . ? C8 N6 C9 C10 1.3(6) . . . . ? C7 N5 C10 C9 -0.2(5) . . . . ? Cu1 N5 C10 C9 178.7(3) . . . . ? N6 C9 C10 N5 -1.2(6) . . . . ? Cu1 O9 N7 O7 -104.2(6) . . . . ? Cu1 O9 N7 O8 76.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.696 _refine_diff_density_min -0.498 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 878698' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cc #TrackingRef 'cc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 Cl4 Cu2 N12' _chemical_formula_weight 693.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 14.870(6) _cell_length_b 19.709(8) _cell_length_c 8.759(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.423(4) _cell_angle_gamma 90.00 _cell_volume 2462.3(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1711 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 25.61 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.870 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 2.201 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6550 _exptl_absorpt_correction_T_max 0.7337 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5731 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 25.48 _reflns_number_total 2268 _reflns_number_gt 1665 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^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 2268 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0513 _refine_ls_wR_factor_gt 0.0483 _refine_ls_goodness_of_fit_ref 1.580 _refine_ls_restrained_S_all 1.580 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.13948(3) 0.28065(2) 0.40818(5) 0.03128(13) Uani 1 1 d . . . C1 C 0.0874(2) 0.13392(16) 0.4286(4) 0.0366(10) Uani 1 1 d . . . H1 H 0.1384 0.1221 0.3923 0.044 Uiso 1 1 calc R . . C2 C 0.0322(3) 0.08385(17) 0.4652(4) 0.0452(11) Uani 1 1 d . . . H2 H 0.0465 0.0389 0.4501 0.054 Uiso 1 1 calc R . . C3 C -0.0585(2) 0.16191(18) 0.5366(4) 0.0400(10) Uani 1 1 d . . . H3 H -0.1088 0.1730 0.5751 0.048 Uiso 1 1 calc R . . C4 C -0.0064(2) 0.21414(18) 0.4985(4) 0.0306(8) Uani 1 1 d . . . C5 C -0.0240(2) 0.28633(18) 0.5098(4) 0.0276(8) Uani 1 1 d . . . C6 C 0.0979(2) 0.41791(16) 0.4045(4) 0.0279(9) Uani 1 1 d . . . C7 C 0.1045(2) 0.48875(16) 0.3825(4) 0.0367(10) Uani 1 1 d . . . H7 H 0.0639 0.5186 0.4119 0.044 Uiso 1 1 calc R . . C8 C 0.1706(3) 0.51191(17) 0.3183(4) 0.0412(10) Uani 1 1 d . . . H8 H 0.1768 0.5580 0.3008 0.049 Uiso 1 1 calc R . . C9 C 0.2297(2) 0.46407(19) 0.2789(4) 0.0350(9) Uani 1 1 d . . . C10 C -0.1028(2) 0.31400(15) 0.5640(4) 0.0391(10) Uani 1 1 d . . . H10A H -0.0809 0.3516 0.6344 0.059 Uiso 1 1 calc R . . H10B H -0.1265 0.2793 0.6192 0.059 Uiso 1 1 calc R . . H10C H -0.1519 0.3290 0.4735 0.059 Uiso 1 1 calc R . . Cl1 Cl 0.31766(7) 0.48911(5) 0.19849(12) 0.0579(3) Uani 1 1 d . . . Cl2 Cl 0.24082(6) 0.22640(4) 0.30128(10) 0.0364(2) Uani 1 1 d . . . N1 N 0.06841(18) 0.19865(12) 0.4448(3) 0.0291(7) Uani 1 1 d . . . N2 N -0.0402(2) 0.09660(15) 0.5207(4) 0.0473(9) Uani 1 1 d . . . N3 N 0.03578(18) 0.32451(14) 0.4660(3) 0.0271(7) Uani 1 1 d . . . N4 N 0.03046(18) 0.39308(13) 0.4645(3) 0.0319(7) Uani 1 1 d . . . N5 N 0.15886(19) 0.37564(12) 0.3634(3) 0.0294(7) Uani 1 1 d . . . N6 N 0.22535(19) 0.39908(14) 0.3001(3) 0.0337(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 0.0288(3) 0.0270(2) 0.0418(3) 0.0002(2) 0.0160(2) 0.0018(2) C1 0.034(2) 0.027(2) 0.051(3) 0.0004(18) 0.016(2) -0.0011(19) C2 0.051(3) 0.024(2) 0.065(3) 0.000(2) 0.024(2) 0.000(2) C3 0.034(2) 0.041(2) 0.051(3) 0.002(2) 0.022(2) -0.002(2) C4 0.028(2) 0.030(2) 0.034(2) -0.0005(18) 0.0085(17) 0.0002(19) C5 0.023(2) 0.032(2) 0.028(2) 0.0023(17) 0.0087(16) 0.0023(19) C6 0.028(2) 0.026(2) 0.027(2) -0.0002(17) 0.0053(18) -0.0001(18) C7 0.034(2) 0.030(2) 0.049(3) -0.0013(19) 0.016(2) 0.0046(18) C8 0.049(3) 0.024(2) 0.051(3) 0.0055(19) 0.015(2) -0.002(2) C9 0.031(2) 0.040(2) 0.036(2) 0.0070(19) 0.0131(18) -0.007(2) C10 0.034(2) 0.042(2) 0.048(3) -0.0038(19) 0.023(2) 0.0021(18) Cl1 0.0521(7) 0.0606(7) 0.0696(8) 0.0165(6) 0.0311(6) -0.0111(6) Cl2 0.0345(6) 0.0404(6) 0.0389(6) -0.0038(5) 0.0177(4) 0.0049(5) N1 0.0307(19) 0.0244(17) 0.0341(18) -0.0013(13) 0.0120(15) -0.0006(13) N2 0.045(2) 0.036(2) 0.069(2) 0.0027(17) 0.0299(19) -0.0058(17) N3 0.0244(18) 0.0251(17) 0.0336(19) 0.0002(13) 0.0113(14) 0.0021(14) N4 0.033(2) 0.0223(17) 0.045(2) 0.0000(14) 0.0187(16) 0.0006(14) N5 0.0242(18) 0.0280(17) 0.0389(19) 0.0016(14) 0.0136(15) 0.0018(14) N6 0.032(2) 0.0336(19) 0.0394(19) 0.0029(15) 0.0156(15) -0.0014(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 1.955(3) . ? Cu1 N5 1.951(3) . ? Cu1 N1 2.006(3) . ? Cu1 Cl2 2.2558(10) . ? Cu1 Cl2 2.6650(12) 7_556 ? C1 N1 1.323(3) . ? C1 C2 1.378(4) . ? C1 H1 0.9300 . ? C2 N2 1.324(4) . ? C2 H2 0.9300 . ? C3 N2 1.331(4) . ? C3 C4 1.385(4) . ? C3 H3 0.9300 . ? C4 N1 1.359(4) . ? C4 C5 1.455(4) . ? C5 N3 1.303(4) . ? C5 C10 1.486(4) . ? C6 N4 1.349(3) . ? C6 N5 1.353(3) . ? C6 C7 1.417(4) . ? C7 C8 1.342(4) . ? C7 H7 0.9300 . ? C8 C9 1.398(4) . ? C8 H8 0.9300 . ? C9 N6 1.298(4) . ? C9 Cl1 1.723(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? Cl2 Cu1 2.6650(12) 7_556 ? N3 N4 1.354(3) . ? N5 N6 1.345(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cu1 N5 78.46(11) . . ? N3 Cu1 N1 79.92(12) . . ? N5 Cu1 N1 156.90(11) . . ? N3 Cu1 Cl2 170.18(8) . . ? N5 Cu1 Cl2 102.56(8) . . ? N1 Cu1 Cl2 97.38(8) . . ? N3 Cu1 Cl2 97.95(8) . 7_556 ? N5 Cu1 Cl2 98.35(8) . 7_556 ? N1 Cu1 Cl2 92.59(8) . 7_556 ? Cl2 Cu1 Cl2 91.58(4) . 7_556 ? N1 C1 C2 120.4(3) . . ? N1 C1 H1 119.8 . . ? C2 C1 H1 119.8 . . ? N2 C2 C1 123.3(3) . . ? N2 C2 H2 118.4 . . ? C1 C2 H2 118.4 . . ? N2 C3 C4 123.2(3) . . ? N2 C3 H3 118.4 . . ? C4 C3 H3 118.4 . . ? N1 C4 C3 119.0(3) . . ? N1 C4 C5 115.1(3) . . ? C3 C4 C5 125.9(3) . . ? N3 C5 C4 113.2(3) . . ? N3 C5 C10 123.2(3) . . ? C4 C5 C10 123.7(3) . . ? N4 C6 N5 120.6(3) . . ? N4 C6 C7 119.9(3) . . ? N5 C6 C7 119.5(3) . . ? C8 C7 C6 118.6(3) . . ? C8 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? C7 C8 C9 117.4(3) . . ? C7 C8 H8 121.3 . . ? C9 C8 H8 121.3 . . ? N6 C9 C8 124.7(3) . . ? N6 C9 Cl1 114.5(3) . . ? C8 C9 Cl1 120.7(3) . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? Cu1 Cl2 Cu1 88.42(4) . 7_556 ? C1 N1 C4 118.3(3) . . ? C1 N1 Cu1 128.4(2) . . ? C4 N1 Cu1 113.2(2) . . ? C3 N2 C2 115.7(3) . . ? C5 N3 N4 122.5(3) . . ? C5 N3 Cu1 118.4(2) . . ? N4 N3 Cu1 119.1(2) . . ? C6 N4 N3 108.5(3) . . ? N6 N5 C6 121.6(3) . . ? N6 N5 Cu1 125.5(2) . . ? C6 N5 Cu1 112.9(2) . . ? C9 N6 N5 118.1(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -1.5(6) . . . . ? N2 C3 C4 N1 -1.2(5) . . . . ? N2 C3 C4 C5 178.5(3) . . . . ? N1 C4 C5 N3 -0.1(4) . . . . ? C3 C4 C5 N3 -179.8(3) . . . . ? N1 C4 C5 C10 179.3(3) . . . . ? C3 C4 C5 C10 -0.4(5) . . . . ? N4 C6 C7 C8 -178.1(3) . . . . ? N5 C6 C7 C8 1.2(5) . . . . ? C6 C7 C8 C9 -0.7(5) . . . . ? C7 C8 C9 N6 -0.1(6) . . . . ? C7 C8 C9 Cl1 -179.1(3) . . . . ? N3 Cu1 Cl2 Cu1 -166.2(5) . . . 7_556 ? N5 Cu1 Cl2 Cu1 98.92(8) . . . 7_556 ? N1 Cu1 Cl2 Cu1 -92.82(8) . . . 7_556 ? Cl2 Cu1 Cl2 Cu1 0.0 7_556 . . 7_556 ? C2 C1 N1 C4 0.2(5) . . . . ? C2 C1 N1 Cu1 177.5(2) . . . . ? C3 C4 N1 C1 1.1(5) . . . . ? C5 C4 N1 C1 -178.7(3) . . . . ? C3 C4 N1 Cu1 -176.6(2) . . . . ? C5 C4 N1 Cu1 3.6(4) . . . . ? N3 Cu1 N1 C1 178.3(3) . . . . ? N5 Cu1 N1 C1 157.5(3) . . . . ? Cl2 Cu1 N1 C1 7.9(3) . . . . ? Cl2 Cu1 N1 C1 -84.0(3) 7_556 . . . ? N3 Cu1 N1 C4 -4.2(2) . . . . ? N5 Cu1 N1 C4 -25.1(4) . . . . ? Cl2 Cu1 N1 C4 -174.7(2) . . . . ? Cl2 Cu1 N1 C4 93.4(2) 7_556 . . . ? C4 C3 N2 C2 0.0(5) . . . . ? C1 C2 N2 C3 1.4(5) . . . . ? C4 C5 N3 N4 178.6(3) . . . . ? C10 C5 N3 N4 -0.8(5) . . . . ? C4 C5 N3 Cu1 -3.7(4) . . . . ? C10 C5 N3 Cu1 176.9(2) . . . . ? N5 Cu1 N3 C5 176.3(3) . . . . ? N1 Cu1 N3 C5 4.5(2) . . . . ? Cl2 Cu1 N3 C5 79.3(6) . . . . ? Cl2 Cu1 N3 C5 -86.7(2) 7_556 . . . ? N5 Cu1 N3 N4 -5.9(2) . . . . ? N1 Cu1 N3 N4 -177.8(2) . . . . ? Cl2 Cu1 N3 N4 -103.0(5) . . . . ? Cl2 Cu1 N3 N4 91.0(2) 7_556 . . . ? N5 C6 N4 N3 -2.4(4) . . . . ? C7 C6 N4 N3 176.8(3) . . . . ? C5 N3 N4 C6 -176.2(3) . . . . ? Cu1 N3 N4 C6 6.2(3) . . . . ? N4 C6 N5 N6 178.5(3) . . . . ? C7 C6 N5 N6 -0.8(5) . . . . ? N4 C6 N5 Cu1 -2.1(4) . . . . ? C7 C6 N5 Cu1 178.6(2) . . . . ? N3 Cu1 N5 N6 -176.6(3) . . . . ? N1 Cu1 N5 N6 -155.6(3) . . . . ? Cl2 Cu1 N5 N6 -6.6(3) . . . . ? Cl2 Cu1 N5 N6 86.9(3) 7_556 . . . ? N3 Cu1 N5 C6 4.1(2) . . . . ? N1 Cu1 N5 C6 25.0(4) . . . . ? Cl2 Cu1 N5 C6 174.1(2) . . . . ? Cl2 Cu1 N5 C6 -92.4(2) 7_556 . . . ? C8 C9 N6 N5 0.6(5) . . . . ? Cl1 C9 N6 N5 179.6(2) . . . . ? C6 N5 N6 C9 -0.1(5) . . . . ? Cu1 N5 N6 C9 -179.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.48 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.653 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.081 _database_code_depnum_ccdc_archive 'CCDC 878699' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_c2c #TrackingRef 'c2c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H17 Cl3 Cu2 N12 O5' _chemical_formula_weight 738.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 14.641(7) _cell_length_b 14.569(7) _cell_length_c 12.478(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.490(4) _cell_angle_gamma 90.00 _cell_volume 2653(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2577 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 23.97 _exptl_crystal_description block _exptl_crystal_colour dark _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.850 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 1.965 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5811 _exptl_absorpt_correction_T_max 0.6499 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9482 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2472 _reflns_number_gt 1909 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0388P)^2^+3.9528P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2472 _refine_ls_number_parameters 194 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0883 _refine_ls_wR_factor_gt 0.0799 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.40372(3) 1.02434(3) 0.18781(3) 0.04166(15) Uani 1 1 d . . . C1 C 0.6244(2) 0.8765(2) 0.0955(3) 0.0439(8) Uani 1 1 d . . . C2 C 0.5849(3) 0.8126(2) 0.0216(3) 0.0525(9) Uani 1 1 d . . . H2 H 0.6211 0.7710 -0.0124 0.063 Uiso 1 1 calc R . . C3 C 0.4940(3) 0.8132(2) 0.0015(3) 0.0515(9) Uani 1 1 d . . . H3 H 0.4653 0.7708 -0.0456 0.062 Uiso 1 1 calc R . . C4 C 0.4417(2) 0.8799(2) 0.0533(3) 0.0407(8) Uani 1 1 d . . . C5 C 0.2328(2) 0.9778(2) 0.0865(3) 0.0477(8) Uani 1 1 d . . . C6 C 0.2146(2) 1.0557(2) 0.1549(3) 0.0483(9) Uani 1 1 d . . . C7 C 0.2757(3) 1.1617(2) 0.2769(3) 0.0543(9) Uani 1 1 d . . . H7 H 0.3256 1.1866 0.3178 0.065 Uiso 1 1 calc R . . C8 C 0.1895(3) 1.1981(3) 0.2846(4) 0.0678(11) Uani 1 1 d . . . H8 H 0.1826 1.2470 0.3312 0.081 Uiso 1 1 calc R . . C9 C 0.1294(3) 1.0947(3) 0.1653(4) 0.0666(11) Uani 1 1 d . . . H9 H 0.0788 1.0698 0.1261 0.080 Uiso 1 1 calc R . . C10 C 0.1612(3) 0.9318(3) 0.0151(3) 0.0699(12) Uani 1 1 d . . . H10A H 0.1594 0.9585 -0.0553 0.105 Uiso 1 1 calc R . . H10B H 0.1027 0.9394 0.0438 0.105 Uiso 1 1 calc R . . H10C H 0.1751 0.8675 0.0106 0.105 Uiso 1 1 calc R . . Cl1 Cl 0.74137(6) 0.87597(7) 0.12691(8) 0.0599(3) Uani 1 1 d . . . Cl2 Cl 0.5000 0.36492(9) 0.2500 0.0598(4) Uani 1 2 d S . . N1 N 0.57811(18) 0.93623(18) 0.1455(2) 0.0411(6) Uani 1 1 d . . . N2 N 0.48645(18) 0.93896(18) 0.1227(2) 0.0404(6) Uani 1 1 d . . . N3 N 0.35065(19) 0.88450(19) 0.0339(2) 0.0473(7) Uani 1 1 d . . . N4 N 0.31852(18) 0.95417(18) 0.0935(2) 0.0428(7) Uani 1 1 d . . . N5 N 0.28826(19) 1.09206(19) 0.2121(2) 0.0456(7) Uani 1 1 d . . . N6 N 0.1168(3) 1.1659(3) 0.2284(3) 0.0769(11) Uani 1 1 d . . . O1 O 0.5000 1.0987(2) 0.2500 0.0512(9) Uani 1 2 d SD . . O2 O 0.4669(3) 0.4175(4) 0.1653(5) 0.175(2) Uani 1 1 d . . . O3 O 0.4280(3) 0.3112(3) 0.2789(4) 0.154(2) Uani 1 1 d . . . H1W H 0.5000 1.1581(14) 0.2500 0.075(19) Uiso 1 2 d SD . . 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 0.0362(2) 0.0429(2) 0.0451(3) -0.00178(19) -0.00137(17) 0.00193(18) C1 0.045(2) 0.0446(19) 0.043(2) 0.0085(16) 0.0073(16) 0.0032(15) C2 0.062(3) 0.050(2) 0.046(2) -0.0029(17) 0.0049(18) 0.0120(18) C3 0.065(3) 0.0446(19) 0.043(2) -0.0050(16) -0.0041(18) 0.0029(17) C4 0.046(2) 0.0409(18) 0.0349(18) 0.0042(14) 0.0015(15) -0.0039(14) C5 0.0391(19) 0.058(2) 0.045(2) 0.0089(18) 0.0007(15) -0.0088(17) C6 0.0376(19) 0.054(2) 0.053(2) 0.0174(17) 0.0034(17) -0.0013(16) C7 0.057(2) 0.051(2) 0.056(2) 0.0005(18) 0.0091(18) 0.0060(18) C8 0.070(3) 0.057(2) 0.080(3) 0.004(2) 0.025(2) 0.014(2) C9 0.041(2) 0.074(3) 0.084(3) 0.012(2) 0.001(2) 0.002(2) C10 0.044(2) 0.093(3) 0.071(3) -0.008(2) -0.004(2) -0.012(2) Cl1 0.0431(5) 0.0671(6) 0.0703(7) 0.0030(5) 0.0088(4) 0.0087(4) Cl2 0.0614(9) 0.0468(7) 0.0716(9) 0.000 0.0086(7) 0.000 N1 0.0373(15) 0.0438(15) 0.0421(16) 0.0035(13) 0.0031(12) -0.0001(12) N2 0.0393(16) 0.0444(15) 0.0372(15) -0.0020(12) 0.0005(12) -0.0003(12) N3 0.0468(17) 0.0496(17) 0.0448(17) -0.0023(14) -0.0010(13) -0.0057(13) N4 0.0419(16) 0.0449(16) 0.0408(16) 0.0057(13) -0.0015(13) -0.0019(12) N5 0.0412(16) 0.0489(17) 0.0467(17) 0.0072(14) 0.0038(13) 0.0043(13) N6 0.057(2) 0.076(3) 0.100(3) 0.008(2) 0.022(2) 0.0165(19) O1 0.0428(19) 0.0353(19) 0.073(2) 0.000 -0.0103(17) 0.000 O2 0.092(3) 0.196(5) 0.237(5) 0.155(4) 0.018(3) 0.021(3) O3 0.127(3) 0.173(4) 0.155(4) 0.082(3) -0.031(3) -0.087(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 O1 1.8952(19) . ? Cu1 N4 1.938(3) . ? Cu1 N2 1.957(3) . ? Cu1 N5 2.001(3) . ? Cu1 N1 2.441(3) 2_655 ? C1 N1 1.293(4) . ? C1 C2 1.402(5) . ? C1 Cl1 1.727(4) . ? C2 C3 1.336(5) . ? C2 H2 0.9300 . ? C3 C4 1.423(5) . ? C3 H3 0.9300 . ? C4 N3 1.338(4) . ? C4 N2 1.353(4) . ? C5 N4 1.297(4) . ? C5 C6 1.457(5) . ? C5 C10 1.483(5) . ? C6 N5 1.354(4) . ? C6 C9 1.385(5) . ? C7 N5 1.319(4) . ? C7 C8 1.379(5) . ? C7 H7 0.9300 . ? C8 N6 1.315(5) . ? C8 H8 0.9300 . ? C9 N6 1.323(5) . ? C9 H9 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? Cl2 O2 1.363(4) 2_655 ? Cl2 O2 1.363(4) . ? Cl2 O3 1.383(4) . ? Cl2 O3 1.383(4) 2_655 ? N1 N2 1.350(4) . ? N1 Cu1 2.441(3) 2_655 ? N3 N4 1.364(4) . ? O1 Cu1 1.8952(19) 2_655 ? O1 H1W 0.87(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N4 166.64(9) . . ? O1 Cu1 N2 93.94(10) . . ? N4 Cu1 N2 78.60(12) . . ? O1 Cu1 N5 105.43(11) . . ? N4 Cu1 N5 80.85(12) . . ? N2 Cu1 N5 159.10(12) . . ? O1 Cu1 N1 85.62(9) . 2_655 ? N4 Cu1 N1 105.19(10) . 2_655 ? N2 Cu1 N1 89.42(10) . 2_655 ? N5 Cu1 N1 99.62(10) . 2_655 ? N1 C1 C2 124.0(3) . . ? N1 C1 Cl1 116.2(3) . . ? C2 C1 Cl1 119.8(3) . . ? C3 C2 C1 118.2(3) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C2 C3 C4 118.8(3) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? N3 C4 N2 120.6(3) . . ? N3 C4 C3 121.1(3) . . ? N2 C4 C3 118.4(3) . . ? N4 C5 C6 112.9(3) . . ? N4 C5 C10 123.7(4) . . ? C6 C5 C10 123.4(3) . . ? N5 C6 C9 118.4(4) . . ? N5 C6 C5 116.0(3) . . ? C9 C6 C5 125.6(4) . . ? N5 C7 C8 120.7(4) . . ? N5 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? N6 C8 C7 122.2(4) . . ? N6 C8 H8 118.9 . . ? C7 C8 H8 118.9 . . ? N6 C9 C6 123.1(4) . . ? N6 C9 H9 118.5 . . ? C6 C9 H9 118.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 Cl2 O2 111.7(6) 2_655 . ? O2 Cl2 O3 110.3(3) 2_655 . ? O2 Cl2 O3 106.7(2) . . ? O2 Cl2 O3 106.7(2) 2_655 2_655 ? O2 Cl2 O3 110.3(3) . 2_655 ? O3 Cl2 O3 111.1(5) . 2_655 ? C1 N1 N2 117.9(3) . . ? C1 N1 Cu1 137.7(2) . 2_655 ? N2 N1 Cu1 101.81(18) . 2_655 ? N1 N2 C4 122.6(3) . . ? N1 N2 Cu1 124.6(2) . . ? C4 N2 Cu1 112.7(2) . . ? C4 N3 N4 108.7(3) . . ? C5 N4 N3 122.3(3) . . ? C5 N4 Cu1 118.3(2) . . ? N3 N4 Cu1 119.4(2) . . ? C7 N5 C6 118.7(3) . . ? C7 N5 Cu1 129.2(3) . . ? C6 N5 Cu1 112.0(2) . . ? C8 N6 C9 116.9(4) . . ? Cu1 O1 Cu1 110.27(16) . 2_655 ? Cu1 O1 H1W 124.86(8) . . ? Cu1 O1 H1W 124.86(8) 2_655 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 0.0(5) . . . . ? Cl1 C1 C2 C3 178.1(3) . . . . ? C1 C2 C3 C4 1.7(5) . . . . ? C2 C3 C4 N3 178.5(3) . . . . ? C2 C3 C4 N2 -1.3(5) . . . . ? N4 C5 C6 N5 1.4(4) . . . . ? C10 C5 C6 N5 -177.5(3) . . . . ? N4 C5 C6 C9 -178.8(3) . . . . ? C10 C5 C6 C9 2.3(6) . . . . ? N5 C7 C8 N6 -0.3(6) . . . . ? N5 C6 C9 N6 0.1(6) . . . . ? C5 C6 C9 N6 -179.7(4) . . . . ? C2 C1 N1 N2 -2.1(5) . . . . ? Cl1 C1 N1 N2 179.7(2) . . . . ? C2 C1 N1 Cu1 155.3(3) . . . 2_655 ? Cl1 C1 N1 Cu1 -22.9(4) . . . 2_655 ? C1 N1 N2 C4 2.5(4) . . . . ? Cu1 N1 N2 C4 -162.1(2) 2_655 . . . ? C1 N1 N2 Cu1 -179.5(2) . . . . ? Cu1 N1 N2 Cu1 15.9(3) 2_655 . . . ? N3 C4 N2 N1 179.3(3) . . . . ? C3 C4 N2 N1 -0.9(5) . . . . ? N3 C4 N2 Cu1 1.1(4) . . . . ? C3 C4 N2 Cu1 -179.1(2) . . . . ? O1 Cu1 N2 N1 11.8(2) . . . . ? N4 Cu1 N2 N1 -179.4(3) . . . . ? N5 Cu1 N2 N1 170.0(3) . . . . ? N1 Cu1 N2 N1 -73.8(2) 2_655 . . . ? O1 Cu1 N2 C4 -170.0(2) . . . . ? N4 Cu1 N2 C4 -1.2(2) . . . . ? N5 Cu1 N2 C4 -11.8(4) . . . . ? N1 Cu1 N2 C4 104.4(2) 2_655 . . . ? N2 C4 N3 N4 0.0(4) . . . . ? C3 C4 N3 N4 -179.8(3) . . . . ? C6 C5 N4 N3 -178.1(3) . . . . ? C10 C5 N4 N3 0.8(5) . . . . ? C6 C5 N4 Cu1 -0.8(4) . . . . ? C10 C5 N4 Cu1 178.1(3) . . . . ? C4 N3 N4 C5 176.2(3) . . . . ? C4 N3 N4 Cu1 -1.1(3) . . . . ? O1 Cu1 N4 C5 -119.1(5) . . . . ? N2 Cu1 N4 C5 -176.1(3) . . . . ? N5 Cu1 N4 C5 0.1(2) . . . . ? N1 Cu1 N4 C5 97.7(3) 2_655 . . . ? O1 Cu1 N4 N3 58.3(6) . . . . ? N2 Cu1 N4 N3 1.3(2) . . . . ? N5 Cu1 N4 N3 177.5(2) . . . . ? N1 Cu1 N4 N3 -84.9(2) 2_655 . . . ? C8 C7 N5 C6 -1.2(5) . . . . ? C8 C7 N5 Cu1 -178.3(3) . . . . ? C9 C6 N5 C7 1.3(5) . . . . ? C5 C6 N5 C7 -178.8(3) . . . . ? C9 C6 N5 Cu1 178.9(3) . . . . ? C5 C6 N5 Cu1 -1.3(4) . . . . ? O1 Cu1 N5 C7 -14.2(3) . . . . ? N4 Cu1 N5 C7 177.9(3) . . . . ? N2 Cu1 N5 C7 -171.6(3) . . . . ? N1 Cu1 N5 C7 73.9(3) 2_655 . . . ? O1 Cu1 N5 C6 168.6(2) . . . . ? N4 Cu1 N5 C6 0.7(2) . . . . ? N2 Cu1 N5 C6 11.2(4) . . . . ? N1 Cu1 N5 C6 -103.3(2) 2_655 . . . ? C7 C8 N6 C9 1.7(6) . . . . ? C6 C9 N6 C8 -1.6(6) . . . . ? N4 Cu1 O1 Cu1 -98.7(5) . . . 2_655 ? N2 Cu1 O1 Cu1 -43.24(8) . . . 2_655 ? N5 Cu1 O1 Cu1 144.67(9) . . . 2_655 ? N1 Cu1 O1 Cu1 45.88(6) 2_655 . . 2_655 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.415 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.060 _database_code_depnum_ccdc_archive 'CCDC 929081' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_caojin120813_2 #TrackingRef 'caojin120813_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H21 Cl2 Cu2 N13 O6' _chemical_formula_weight 737.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.2535(6) _cell_length_b 11.9210(10) _cell_length_c 12.0912(9) _cell_angle_alpha 92.170(7) _cell_angle_beta 115.524(6) _cell_angle_gamma 107.005(6) _cell_volume 1374.30(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.782 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 1.806 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6308 _exptl_absorpt_correction_T_max 0.6815 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9121 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5114 _reflns_number_gt 4330 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+1.7377P] 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 5114 _refine_ls_number_parameters 395 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0964 _refine_ls_wR_factor_gt 0.0896 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.008 _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 C1 C 0.7313(4) 0.5637(3) 0.6563(4) 0.0441(9) Uani 1 1 d . . . H1 H 0.6414 0.5097 0.6068 0.053 Uiso 1 1 calc R . . C2 C 0.7493(4) 0.6697(3) 0.7246(4) 0.0511(10) Uani 1 1 d . . . H2 H 0.6704 0.6854 0.7175 0.061 Uiso 1 1 calc R . . C3 C 0.9839(4) 0.7224(3) 0.8050(3) 0.0379(8) Uani 1 1 d . . . H3 H 1.0735 0.7755 0.8575 0.046 Uiso 1 1 calc R . . C4 C 0.9704(3) 0.6188(3) 0.7360(3) 0.0305(7) Uani 1 1 d . . . C5 C 1.0874(3) 0.5901(3) 0.7346(3) 0.0322(7) Uani 1 1 d . . . C6 C 1.2371(4) 0.6658(4) 0.8124(4) 0.0521(10) Uani 1 1 d . . . H6A H 1.2831 0.6244 0.8748 0.078 Uiso 1 1 calc R . . H6B H 1.2425 0.7396 0.8521 0.078 Uiso 1 1 calc R . . H6C H 1.2824 0.6821 0.7603 0.078 Uiso 1 1 calc R . . C7 C 1.0743(3) 0.3454(3) 0.5642(3) 0.0327(7) Uani 1 1 d . . . C8 C 1.1498(4) 0.2809(3) 0.5375(3) 0.0417(8) Uani 1 1 d . . . H8 H 1.2471 0.3122 0.5736 0.050 Uiso 1 1 calc R . . C9 C 1.0797(4) 0.1747(3) 0.4599(4) 0.0437(9) Uani 1 1 d . . . H9 H 1.1265 0.1309 0.4404 0.052 Uiso 1 1 calc R . . C10 C 0.9326(4) 0.1315(3) 0.4089(3) 0.0362(8) Uani 1 1 d . . . C11 C 0.9382(4) 0.1450(3) 0.8643(3) 0.0418(8) Uani 1 1 d . . . H11 H 1.0013 0.1469 0.9460 0.050 Uiso 1 1 calc R . . C12 C 0.8595(4) 0.0406(3) 0.7813(3) 0.0391(8) Uani 1 1 d . . . H12 H 0.8671 -0.0314 0.8047 0.047 Uiso 1 1 calc R . . C13 C 0.9207(3) 0.2505(3) 0.8223(3) 0.0340(7) Uani 1 1 d . . . C14 C 0.7649(3) 0.0434(3) 0.6570(3) 0.0308(7) Uani 1 1 d . . . C15 C 0.5066(4) -0.2416(3) 0.3524(4) 0.0447(9) Uani 1 1 d . . . H15A H 0.5474 -0.2571 0.4356 0.067 Uiso 1 1 calc R . . H15B H 0.5482 -0.2675 0.3063 0.067 Uiso 1 1 calc R . . H15C H 0.4075 -0.2844 0.3118 0.067 Uiso 1 1 calc R . . C16 C 0.5325(3) -0.1115(3) 0.3580(3) 0.0330(7) Uani 1 1 d . . . C17 C 0.4680(3) -0.0619(3) 0.2473(3) 0.0354(8) Uani 1 1 d . . . C18 C 0.4405(4) 0.1067(4) 0.1670(3) 0.0458(9) Uani 1 1 d . . . H18 H 0.4597 0.1888 0.1768 0.055 Uiso 1 1 calc R . . C19 C 0.3510(5) 0.0347(4) 0.0492(4) 0.0605(12) Uani 1 1 d . . . H19 H 0.3113 0.0702 -0.0181 0.073 Uiso 1 1 calc R . . C0BA C 0.3796(4) -0.1293(4) 0.1281(4) 0.0491(10) Uani 1 1 d . . . H0BA H 0.3608 -0.2114 0.1166 0.059 Uiso 1 1 calc R . . Cl3 Cl 1.01447(11) 0.38622(8) 0.92410(8) 0.0538(3) Uani 1 1 d . . . Cl4 Cl 0.83573(12) -0.00334(9) 0.30564(10) 0.0548(3) Uani 1 1 d . . . Cu1 Cu 0.63617(4) 0.13672(3) 0.44582(4) 0.03082(12) Uani 1 1 d . . . Cu2 Cu 0.84942(4) 0.39622(3) 0.56972(4) 0.02961(12) Uani 1 1 d . . . H1W H 0.3266 0.4743 0.0462 0.11(2) Uiso 1 1 d R . . H3W H 0.4937 0.5345 0.7643 0.072(15) Uiso 1 1 d RD . . H4W H 0.6204 0.3285 0.4117 0.031(11) Uiso 1 1 d R . . H5W H 0.3547 0.5242 0.6959 0.16(3) Uiso 1 1 d RD . . N1 N 0.8403(3) 0.5390(2) 0.6609(3) 0.0331(6) Uani 1 1 d . . . N2 N 0.8751(3) 0.7488(3) 0.7994(3) 0.0460(8) Uani 1 1 d . . . N3 N 1.0477(3) 0.4919(2) 0.6579(2) 0.0303(6) Uani 1 1 d . . . N4 N 1.1419(3) 0.4529(3) 0.6406(3) 0.0371(7) Uani 1 1 d . . . N5 N 0.9327(3) 0.2966(2) 0.5114(2) 0.0311(6) Uani 1 1 d . . . N6 N 0.8613(3) 0.1889(2) 0.4336(2) 0.0330(6) Uani 1 1 d . . . N7 N 0.8366(3) 0.2542(2) 0.7092(2) 0.0305(6) Uani 1 1 d . . . N8 N 0.7562(3) 0.1495(2) 0.6262(2) 0.0297(6) Uani 1 1 d . . . N9 N 0.6867(3) -0.0583(2) 0.5712(3) 0.0355(6) Uani 1 1 d . . . N10 N 0.6143(3) -0.0300(2) 0.4585(3) 0.0317(6) Uani 1 1 d . . . N11 N 0.4983(3) 0.0590(2) 0.2651(3) 0.0356(6) Uani 1 1 d . . . N12 N 0.3208(4) -0.0824(3) 0.0301(3) 0.0610(10) Uani 1 1 d . . . N13 N 0.3392(8) 0.2911(5) 0.9164(8) 0.120(2) Uani 1 1 d . . . O1 O 0.3676(5) 0.5333(4) 0.1093(4) 0.1052(14) Uani 1 1 d . . . O2 O 0.3545(17) 0.3777(12) 0.8912(14) 0.347(8) Uani 1 1 d . . . O3 O 0.3987(9) 0.2497(6) 0.8871(10) 0.224(4) Uani 1 1 d . . . O4 O 0.2811(7) 0.2730(6) 0.9762(8) 0.177(3) Uani 1 1 d . . . O5 O 0.4347(3) 0.5478(3) 0.6979(4) 0.0865(12) Uani 1 1 d D . . O6 O 0.6582(2) 0.30148(19) 0.4640(2) 0.0331(5) Uani 1 1 d . . . H2W H 0.4542 0.5937 0.1063 0.22(5) Uiso 1 1 d 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 C1 0.0356(18) 0.032(2) 0.064(3) 0.0015(18) 0.0255(18) 0.0076(15) C2 0.050(2) 0.039(2) 0.071(3) 0.001(2) 0.035(2) 0.0160(18) C3 0.046(2) 0.0281(18) 0.0342(18) 0.0008(15) 0.0180(16) 0.0065(15) C4 0.0341(17) 0.0241(17) 0.0274(16) 0.0064(13) 0.0116(14) 0.0058(13) C5 0.0311(16) 0.0293(18) 0.0273(16) 0.0042(14) 0.0092(14) 0.0051(14) C6 0.0337(19) 0.048(2) 0.049(2) -0.0105(19) 0.0044(17) 0.0040(17) C7 0.0307(16) 0.0353(19) 0.0349(18) 0.0100(15) 0.0163(14) 0.0130(14) C8 0.0355(18) 0.049(2) 0.048(2) 0.0122(18) 0.0216(17) 0.0214(17) C9 0.054(2) 0.050(2) 0.052(2) 0.0190(19) 0.0344(19) 0.0332(19) C10 0.051(2) 0.0319(19) 0.0356(18) 0.0093(15) 0.0262(16) 0.0175(16) C11 0.049(2) 0.042(2) 0.0318(18) 0.0080(16) 0.0130(16) 0.0206(17) C12 0.050(2) 0.0307(19) 0.0363(19) 0.0083(15) 0.0161(16) 0.0195(16) C13 0.0402(18) 0.0265(18) 0.0293(17) -0.0016(14) 0.0131(15) 0.0090(14) C14 0.0356(17) 0.0267(17) 0.0331(17) 0.0030(14) 0.0184(14) 0.0110(14) C15 0.0412(19) 0.0268(19) 0.055(2) -0.0059(17) 0.0166(18) 0.0077(15) C16 0.0280(16) 0.0286(18) 0.0383(19) -0.0033(14) 0.0162(14) 0.0039(13) C17 0.0302(16) 0.0321(19) 0.0363(18) -0.0069(15) 0.0144(15) 0.0034(14) C18 0.044(2) 0.039(2) 0.038(2) 0.0016(17) 0.0105(17) 0.0048(17) C19 0.068(3) 0.051(3) 0.038(2) 0.0007(19) 0.009(2) 0.011(2) C0BA 0.048(2) 0.039(2) 0.041(2) -0.0070(17) 0.0100(18) 0.0065(17) Cl3 0.0701(6) 0.0333(5) 0.0325(5) -0.0056(4) 0.0071(4) 0.0102(4) Cl4 0.0771(7) 0.0375(5) 0.0555(6) -0.0028(4) 0.0372(5) 0.0187(5) Cu1 0.0318(2) 0.0220(2) 0.0287(2) -0.00098(16) 0.00959(17) 0.00317(16) Cu2 0.0237(2) 0.0222(2) 0.0365(2) -0.00217(16) 0.01131(17) 0.00423(15) N1 0.0318(14) 0.0252(15) 0.0371(15) 0.0014(12) 0.0147(12) 0.0051(11) N2 0.058(2) 0.0330(17) 0.0504(19) 0.0017(14) 0.0298(16) 0.0129(15) N3 0.0266(13) 0.0264(15) 0.0320(14) 0.0026(12) 0.0107(11) 0.0058(11) N4 0.0243(13) 0.0345(17) 0.0444(17) -0.0001(13) 0.0117(12) 0.0066(12) N5 0.0302(14) 0.0268(15) 0.0359(15) 0.0027(12) 0.0164(12) 0.0080(11) N6 0.0362(14) 0.0275(15) 0.0337(15) 0.0015(12) 0.0168(12) 0.0080(12) N7 0.0360(14) 0.0229(14) 0.0281(14) 0.0006(11) 0.0135(12) 0.0066(11) N8 0.0324(14) 0.0231(14) 0.0286(14) -0.0012(11) 0.0126(12) 0.0056(11) N9 0.0413(15) 0.0234(15) 0.0365(16) -0.0006(12) 0.0148(13) 0.0098(12) N10 0.0313(14) 0.0236(14) 0.0357(15) -0.0025(12) 0.0158(12) 0.0040(11) N11 0.0312(14) 0.0297(16) 0.0349(16) -0.0020(12) 0.0114(12) 0.0027(12) N12 0.063(2) 0.051(2) 0.0369(19) -0.0098(16) 0.0046(17) 0.0081(18) N13 0.172(6) 0.074(4) 0.211(7) 0.076(4) 0.148(6) 0.075(4) O1 0.096(3) 0.103(3) 0.079(3) -0.021(3) 0.028(2) 0.007(3) O2 0.55(2) 0.333(16) 0.431(18) 0.212(14) 0.376(18) 0.276(16) O3 0.291(9) 0.135(6) 0.420(13) 0.092(7) 0.295(10) 0.098(6) O4 0.200(6) 0.152(5) 0.312(9) 0.114(6) 0.200(7) 0.105(5) O5 0.0416(17) 0.103(3) 0.115(3) 0.072(2) 0.0316(19) 0.0264(17) O6 0.0274(11) 0.0248(12) 0.0354(13) 0.0028(10) 0.0063(10) 0.0062(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 C1 N1 1.323(4) . ? C1 C2 1.394(5) . ? C1 H1 0.9300 . ? C2 N2 1.328(5) . ? C2 H2 0.9300 . ? C3 N2 1.325(5) . ? C3 C4 1.396(5) . ? C3 H3 0.9300 . ? C4 N1 1.359(4) . ? C4 C5 1.460(5) . ? C5 N3 1.298(4) . ? C5 C6 1.490(4) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 N4 1.346(4) . ? C7 N5 1.356(4) . ? C7 C8 1.420(5) . ? C8 C9 1.340(5) . ? C8 H8 0.9300 . ? C9 C10 1.408(5) . ? C9 H9 0.9300 . ? C10 N6 1.310(4) . ? C10 Cl4 1.726(4) . ? C11 C12 1.355(5) . ? C11 C13 1.410(5) . ? C11 H11 0.9300 . ? C12 C14 1.428(5) . ? C12 H12 0.9300 . ? C13 N7 1.297(4) . ? C13 Cl3 1.725(3) . ? C14 N9 1.347(4) . ? C14 N8 1.352(4) . ? C15 C16 1.485(5) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 N10 1.301(4) . ? C16 C17 1.464(5) . ? C17 N11 1.365(4) . ? C17 C0BA 1.387(5) . ? C18 N11 1.325(5) . ? C18 C19 1.395(5) . ? C18 H18 0.9300 . ? C19 N12 1.322(5) . ? C19 H19 0.9300 . ? C0BA N12 1.321(5) . ? C0BA H0BA 0.9300 . ? Cu1 O6 1.898(2) . ? Cu1 N10 1.950(3) . ? Cu1 N8 1.980(3) . ? Cu1 N11 2.031(3) . ? Cu2 O6 1.907(2) . ? Cu2 N3 1.946(3) . ? Cu2 N5 1.985(3) . ? Cu2 N1 2.044(3) . ? Cu2 N7 2.452(3) . ? N3 N4 1.362(4) . ? N5 N6 1.354(4) . ? N7 N8 1.358(3) . ? N9 N10 1.368(4) . ? N13 O2 1.073(12) . ? N13 O3 1.095(8) . ? N13 O4 1.156(8) . ? O1 H1W 0.8692 . ? O1 H2W 1.0453 . ? O5 H3W 0.8497 . ? O5 H5W 0.8498 . ? O6 H4W 0.7405 . ? 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 C1 C2 120.9(3) . . ? N1 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? N2 C2 C1 122.4(3) . . ? N2 C2 H2 118.8 . . ? C1 C2 H2 118.8 . . ? N2 C3 C4 123.2(3) . . ? N2 C3 H3 118.4 . . ? C4 C3 H3 118.4 . . ? N1 C4 C3 119.2(3) . . ? N1 C4 C5 116.1(3) . . ? C3 C4 C5 124.6(3) . . ? N3 C5 C4 113.1(3) . . ? N3 C5 C6 123.2(3) . . ? C4 C5 C6 123.7(3) . . ? 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 N5 120.5(3) . . ? N4 C7 C8 120.6(3) . . ? N5 C7 C8 118.9(3) . . ? C9 C8 C7 119.3(3) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 117.8(3) . . ? C8 C9 H9 121.1 . . ? C10 C9 H9 121.1 . . ? N6 C10 C9 123.7(3) . . ? N6 C10 Cl4 116.2(3) . . ? C9 C10 Cl4 120.1(3) . . ? C12 C11 C13 117.5(3) . . ? C12 C11 H11 121.3 . . ? C13 C11 H11 121.3 . . ? C11 C12 C14 118.7(3) . . ? C11 C12 H12 120.7 . . ? C14 C12 H12 120.7 . . ? N7 C13 C11 124.3(3) . . ? N7 C13 Cl3 115.7(3) . . ? C11 C13 Cl3 119.9(3) . . ? N9 C14 N8 120.4(3) . . ? N9 C14 C12 120.4(3) . . ? N8 C14 C12 119.1(3) . . ? C16 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C16 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N10 C16 C17 112.9(3) . . ? N10 C16 C15 124.8(3) . . ? C17 C16 C15 122.3(3) . . ? N11 C17 C0BA 119.0(3) . . ? N11 C17 C16 116.7(3) . . ? C0BA C17 C16 124.3(3) . . ? N11 C18 C19 120.5(4) . . ? N11 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? N12 C19 C18 122.2(4) . . ? N12 C19 H19 118.9 . . ? C18 C19 H19 118.9 . . ? N12 C0BA C17 123.1(4) . . ? N12 C0BA H0BA 118.4 . . ? C17 C0BA H0BA 118.4 . . ? O6 Cu1 N10 168.94(11) . . ? O6 Cu1 N8 93.00(10) . . ? N10 Cu1 N8 78.04(11) . . ? O6 Cu1 N11 107.77(11) . . ? N10 Cu1 N11 80.83(12) . . ? N8 Cu1 N11 158.79(11) . . ? O6 Cu2 N3 172.46(11) . . ? O6 Cu2 N5 96.62(10) . . ? N3 Cu2 N5 78.46(11) . . ? O6 Cu2 N1 104.55(10) . . ? N3 Cu2 N1 80.11(11) . . ? N5 Cu2 N1 158.52(11) . . ? O6 Cu2 N7 84.75(9) . . ? N3 Cu2 N7 100.41(10) . . ? N5 Cu2 N7 85.21(10) . . ? N1 Cu2 N7 100.14(10) . . ? C1 N1 C4 118.0(3) . . ? C1 N1 Cu2 130.5(2) . . ? C4 N1 Cu2 111.5(2) . . ? C3 N2 C2 116.3(3) . . ? C5 N3 N4 121.6(3) . . ? C5 N3 Cu2 119.0(2) . . ? N4 N3 Cu2 119.5(2) . . ? C7 N4 N3 109.2(2) . . ? N6 N5 C7 122.0(3) . . ? N6 N5 Cu2 125.7(2) . . ? C7 N5 Cu2 112.2(2) . . ? C10 N6 N5 118.3(3) . . ? C13 N7 N8 118.3(3) . . ? C13 N7 Cu2 133.7(2) . . ? N8 N7 Cu2 101.46(18) . . ? C14 N8 N7 122.1(3) . . ? C14 N8 Cu1 112.9(2) . . ? N7 N8 Cu1 124.5(2) . . ? C14 N9 N10 108.7(3) . . ? C16 N10 N9 121.7(3) . . ? C16 N10 Cu1 118.5(2) . . ? N9 N10 Cu1 119.74(19) . . ? C18 N11 C17 118.2(3) . . ? C18 N11 Cu1 130.7(2) . . ? C17 N11 Cu1 111.1(2) . . ? C0BA N12 C19 117.0(3) . . ? O2 N13 O3 106.9(9) . . ? O2 N13 O4 114.6(9) . . ? O3 N13 O4 137.7(8) . . ? H1W O1 H2W 109.1 . . ? H3W O5 H5W 108.8 . . ? Cu1 O6 Cu2 110.55(11) . . ? Cu1 O6 H4W 122.8 . . ? Cu2 O6 H4W 114.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -1.8(7) . . . . ? N2 C3 C4 N1 -1.4(5) . . . . ? N2 C3 C4 C5 176.4(3) . . . . ? N1 C4 C5 N3 1.4(4) . . . . ? C3 C4 C5 N3 -176.4(3) . . . . ? N1 C4 C5 C6 -178.9(3) . . . . ? C3 C4 C5 C6 3.3(5) . . . . ? N4 C7 C8 C9 -179.2(3) . . . . ? N5 C7 C8 C9 0.9(5) . . . . ? C7 C8 C9 C10 -0.5(5) . . . . ? C8 C9 C10 N6 -0.4(5) . . . . ? C8 C9 C10 Cl4 178.6(3) . . . . ? C13 C11 C12 C14 0.2(5) . . . . ? C12 C11 C13 N7 -1.4(5) . . . . ? C12 C11 C13 Cl3 178.5(3) . . . . ? C11 C12 C14 N9 178.9(3) . . . . ? C11 C12 C14 N8 -0.2(5) . . . . ? N10 C16 C17 N11 -1.9(4) . . . . ? C15 C16 C17 N11 178.9(3) . . . . ? N10 C16 C17 C0BA 178.3(3) . . . . ? C15 C16 C17 C0BA -0.9(5) . . . . ? N11 C18 C19 N12 -0.4(7) . . . . ? N11 C17 C0BA N12 -1.0(6) . . . . ? C16 C17 C0BA N12 178.8(4) . . . . ? C2 C1 N1 C4 1.3(5) . . . . ? C2 C1 N1 Cu2 -178.0(3) . . . . ? C3 C4 N1 C1 0.2(5) . . . . ? C5 C4 N1 C1 -177.8(3) . . . . ? C3 C4 N1 Cu2 179.6(2) . . . . ? C5 C4 N1 Cu2 1.7(3) . . . . ? O6 Cu2 N1 C1 2.5(3) . . . . ? N3 Cu2 N1 C1 176.4(3) . . . . ? N5 Cu2 N1 C1 172.5(3) . . . . ? N7 Cu2 N1 C1 -84.6(3) . . . . ? O6 Cu2 N1 C4 -176.9(2) . . . . ? N3 Cu2 N1 C4 -2.9(2) . . . . ? N5 Cu2 N1 C4 -6.9(4) . . . . ? N7 Cu2 N1 C4 96.0(2) . . . . ? C4 C3 N2 C2 0.9(5) . . . . ? C1 C2 N2 C3 0.6(6) . . . . ? C4 C5 N3 N4 177.7(3) . . . . ? C6 C5 N3 N4 -2.0(5) . . . . ? C4 C5 N3 Cu2 -4.2(4) . . . . ? C6 C5 N3 Cu2 176.1(3) . . . . ? O6 Cu2 N3 C5 132.8(7) . . . . ? N5 Cu2 N3 C5 -177.4(3) . . . . ? N1 Cu2 N3 C5 4.1(2) . . . . ? N7 Cu2 N3 C5 -94.5(3) . . . . ? O6 Cu2 N3 N4 -49.0(9) . . . . ? N5 Cu2 N3 N4 0.8(2) . . . . ? N1 Cu2 N3 N4 -177.7(3) . . . . ? N7 Cu2 N3 N4 83.7(2) . . . . ? N5 C7 N4 N3 4.2(4) . . . . ? C8 C7 N4 N3 -175.7(3) . . . . ? C5 N3 N4 C7 175.3(3) . . . . ? Cu2 N3 N4 C7 -2.8(4) . . . . ? N4 C7 N5 N6 179.6(3) . . . . ? C8 C7 N5 N6 -0.5(5) . . . . ? N4 C7 N5 Cu2 -3.7(4) . . . . ? C8 C7 N5 Cu2 176.2(2) . . . . ? O6 Cu2 N5 N6 -7.8(3) . . . . ? N3 Cu2 N5 N6 178.0(3) . . . . ? N1 Cu2 N5 N6 -178.0(3) . . . . ? N7 Cu2 N5 N6 76.3(3) . . . . ? O6 Cu2 N5 C7 175.7(2) . . . . ? N3 Cu2 N5 C7 1.4(2) . . . . ? N1 Cu2 N5 C7 5.4(4) . . . . ? N7 Cu2 N5 C7 -100.2(2) . . . . ? C9 C10 N6 N5 0.8(5) . . . . ? Cl4 C10 N6 N5 -178.2(2) . . . . ? C7 N5 N6 C10 -0.4(5) . . . . ? Cu2 N5 N6 C10 -176.6(2) . . . . ? C11 C13 N7 N8 2.3(5) . . . . ? Cl3 C13 N7 N8 -177.6(2) . . . . ? C11 C13 N7 Cu2 -143.5(3) . . . . ? Cl3 C13 N7 Cu2 36.7(4) . . . . ? O6 Cu2 N7 C13 -171.7(3) . . . . ? N3 Cu2 N7 C13 13.8(3) . . . . ? N5 Cu2 N7 C13 91.1(3) . . . . ? N1 Cu2 N7 C13 -67.9(3) . . . . ? O6 Cu2 N7 N8 38.62(18) . . . . ? N3 Cu2 N7 N8 -135.81(18) . . . . ? N5 Cu2 N7 N8 -58.49(18) . . . . ? N1 Cu2 N7 N8 142.50(18) . . . . ? N9 C14 N8 N7 -177.9(3) . . . . ? C12 C14 N8 N7 1.1(4) . . . . ? N9 C14 N8 Cu1 -5.7(4) . . . . ? C12 C14 N8 Cu1 173.3(2) . . . . ? C13 N7 N8 C14 -2.2(4) . . . . ? Cu2 N7 N8 C14 153.3(2) . . . . ? C13 N7 N8 Cu1 -173.4(2) . . . . ? Cu2 N7 N8 Cu1 -17.9(2) . . . . ? O6 Cu1 N8 C14 177.4(2) . . . . ? N10 Cu1 N8 C14 3.9(2) . . . . ? N11 Cu1 N8 C14 8.9(4) . . . . ? O6 Cu1 N8 N7 -10.6(2) . . . . ? N10 Cu1 N8 N7 175.9(3) . . . . ? N11 Cu1 N8 N7 -179.1(3) . . . . ? N8 C14 N9 N10 3.9(4) . . . . ? C12 C14 N9 N10 -175.1(3) . . . . ? C17 C16 N10 N9 -178.5(3) . . . . ? C15 C16 N10 N9 0.6(5) . . . . ? C17 C16 N10 Cu1 0.1(4) . . . . ? C15 C16 N10 Cu1 179.2(3) . . . . ? C14 N9 N10 C16 178.4(3) . . . . ? C14 N9 N10 Cu1 -0.2(3) . . . . ? O6 Cu1 N10 C16 142.8(5) . . . . ? N8 Cu1 N10 C16 179.2(3) . . . . ? N11 Cu1 N10 C16 1.1(2) . . . . ? O6 Cu1 N10 N9 -38.5(6) . . . . ? N8 Cu1 N10 N9 -2.1(2) . . . . ? N11 Cu1 N10 N9 179.7(2) . . . . ? C19 C18 N11 C17 0.1(5) . . . . ? C19 C18 N11 Cu1 177.7(3) . . . . ? C0BA C17 N11 C18 0.5(5) . . . . ? C16 C17 N11 C18 -179.3(3) . . . . ? C0BA C17 N11 Cu1 -177.5(3) . . . . ? C16 C17 N11 Cu1 2.7(3) . . . . ? O6 Cu1 N11 C18 7.5(3) . . . . ? N10 Cu1 N11 C18 -179.7(3) . . . . ? N8 Cu1 N11 C18 175.3(3) . . . . ? O6 Cu1 N11 C17 -174.8(2) . . . . ? N10 Cu1 N11 C17 -2.0(2) . . . . ? N8 Cu1 N11 C17 -7.0(4) . . . . ? C17 C0BA N12 C19 0.8(6) . . . . ? C18 C19 N12 C0BA -0.1(7) . . . . ? N10 Cu1 O6 Cu2 79.8(5) . . . . ? N8 Cu1 O6 Cu2 44.30(13) . . . . ? N11 Cu1 O6 Cu2 -140.07(12) . . . . ? N3 Cu2 O6 Cu1 85.6(8) . . . . ? N5 Cu2 O6 Cu1 36.71(14) . . . . ? N1 Cu2 O6 Cu1 -146.98(12) . . . . ? N7 Cu2 O6 Cu1 -47.84(12) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.771 _refine_diff_density_min -0.764 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 929082'