Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Chun-Ying Duan' _publ_contact_author_address ; Coordination Chemistry Institute State Key Laboratory of Coordination Chemistry Nanjing University Nanjing 210093 CHINA ; _publ_contact_author_email DUANCY@NJU.EDU.CN _publ_section_title ; Metal Complexes Formed by Metal-Assisted Solvolysis of Di-2-pyridylketone Azone: Structures and Magnetic Properties ; loop_ _publ_author_name 'Duan Chun-Ying.' 'Weijie Hua.' 'Wei Huang.' 'Shuhua Li.' 'Qing-Jin Meng.' ; You Song ; 'Dayu Wu.' # Attachment 'compound 1.CIF' data_t _database_code_depnum_ccdc_archive 'CCDC 631554' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H48 N20 Ni4 O10' _chemical_formula_weight 1299.90 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.4319(10) _cell_length_b 10.9629(8) _cell_length_c 20.1630(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.5860(10) _cell_angle_gamma 90.00 _cell_volume 2968.9(4) _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 dark-blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 1.319 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.729 _exptl_absorpt_correction_T_max 0.785 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 14570 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0468 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5205 _reflns_number_gt 3903 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1255P)^2^+0.7556P] 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 5205 _refine_ls_number_parameters 377 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1857 _refine_ls_wR_factor_gt 0.1715 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.061 _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 Ni1 Ni 0.42939(5) 0.61050(5) 0.51431(3) 0.0334(2) Uani 1 1 d . . . Ni2 Ni 0.33195(5) 0.35686(6) 0.50522(3) 0.0359(2) Uani 1 1 d . . . O1 O 0.4581(2) 0.4423(3) 0.55107(14) 0.0326(7) Uani 1 1 d . . . O2 O 0.5481(3) 0.4470(4) 0.65099(17) 0.0535(10) Uani 1 1 d . . . H2A H 0.5905 0.4595 0.6229 0.080 Uiso 1 1 calc R . . O3 O 0.3287(2) 0.5149(3) 0.45210(15) 0.0347(7) Uani 1 1 d . . . O4 O 0.1766(3) 0.5448(4) 0.39662(18) 0.0497(9) Uani 1 1 d . . . N1 N 0.0780(7) 0.1684(8) 0.4999(5) 0.124(3) Uani 1 1 d U . . N2 N 0.1593(6) 0.2090(7) 0.4749(4) 0.096(2) Uani 1 1 d U . . N3 N 0.2337(4) 0.2455(4) 0.4536(3) 0.0549(12) Uani 1 1 d . . . N4 N 0.5571(5) 0.8100(7) 0.6526(3) 0.096(2) Uani 1 1 d U . . N5 N 0.5536(4) 0.7609(4) 0.6025(2) 0.0530(12) Uani 1 1 d . . . N6 N 0.5486(3) 0.7121(4) 0.5499(2) 0.0403(10) Uani 1 1 d . . . N7 N 0.3593(3) 0.2479(4) 0.5887(2) 0.0418(10) Uani 1 1 d . . . N8 N 0.3592(3) 0.6169(4) 0.6067(2) 0.0381(9) Uani 1 1 d . . . N9 N 0.3520(3) 0.7484(4) 0.4699(2) 0.0417(10) Uani 1 1 d . . . N10 N 0.2097(3) 0.4499(4) 0.5464(2) 0.0413(10) Uani 1 1 d . . . C1 C 0.3269(5) 0.1337(5) 0.5986(3) 0.0566(15) Uani 1 1 d . . . H1A H 0.2853 0.0988 0.5667 0.068 Uiso 1 1 calc R . . C2 C 0.3517(6) 0.0670(6) 0.6526(3) 0.0712(19) Uani 1 1 d . . . H2B H 0.3268 -0.0114 0.6583 0.085 Uiso 1 1 calc R . . C3 C 0.4148(6) 0.1179(6) 0.6989(3) 0.0683(19) Uani 1 1 d . . . H3B H 0.4337 0.0731 0.7361 0.082 Uiso 1 1 calc R . . C4 C 0.4501(5) 0.2339(5) 0.6908(3) 0.0567(15) Uani 1 1 d . . . H4A H 0.4929 0.2692 0.7219 0.068 Uiso 1 1 calc R . . C5 C 0.4193(4) 0.2976(5) 0.6341(2) 0.0394(11) Uani 1 1 d . . . C6 C 0.4543(4) 0.4273(5) 0.6193(2) 0.0382(11) Uani 1 1 d . . . C7 C 0.3841(4) 0.5242(5) 0.6483(2) 0.0393(12) Uani 1 1 d . . . C8 C 0.3528(5) 0.5221(6) 0.7128(3) 0.0586(16) Uani 1 1 d . . . H8A H 0.3706 0.4585 0.7411 0.070 Uiso 1 1 calc R . . C9 C 0.2938(6) 0.6176(6) 0.7346(3) 0.076(2) Uani 1 1 d . . . H9A H 0.2733 0.6194 0.7785 0.091 Uiso 1 1 calc R . . C10 C 0.2661(6) 0.7074(6) 0.6931(3) 0.0708(19) Uani 1 1 d . . . H10A H 0.2242 0.7695 0.7074 0.085 Uiso 1 1 calc R . . C11 C 0.3004(4) 0.7059(5) 0.6296(3) 0.0513(14) Uani 1 1 d . . . H11A H 0.2823 0.7690 0.6012 0.062 Uiso 1 1 calc R . . C12 C 0.3791(5) 0.8668(5) 0.4664(3) 0.0541(14) Uani 1 1 d . . . H12A H 0.4417 0.8892 0.4822 0.065 Uiso 1 1 calc R . . C13 C 0.3185(5) 0.9548(6) 0.4406(3) 0.0643(17) Uani 1 1 d . . . H13A H 0.3391 1.0357 0.4395 0.077 Uiso 1 1 calc R . . C14 C 0.2269(6) 0.9219(6) 0.4165(3) 0.0692(19) Uani 1 1 d . . . H14A H 0.1847 0.9806 0.3983 0.083 Uiso 1 1 calc R . . C15 C 0.1963(5) 0.7990(6) 0.4192(3) 0.0582(16) Uani 1 1 d . . . H15A H 0.1340 0.7748 0.4036 0.070 Uiso 1 1 calc R . . C16 C 0.2636(4) 0.7154(5) 0.4461(3) 0.0426(12) Uani 1 1 d . . . C17 C 0.2410(4) 0.5782(5) 0.4507(2) 0.0380(11) Uani 1 1 d . . . C18 C 0.1778(4) 0.5473(5) 0.5123(3) 0.0428(12) Uani 1 1 d . . . C19 C 0.0937(4) 0.6101(5) 0.5299(3) 0.0522(14) Uani 1 1 d . . . H19A H 0.0728 0.6771 0.5051 0.063 Uiso 1 1 calc R . . C20 C 0.0415(5) 0.5742(6) 0.5832(3) 0.0651(17) Uani 1 1 d . . . H20A H -0.0152 0.6168 0.5957 0.078 Uiso 1 1 calc R . . C21 C 0.0724(4) 0.4749(6) 0.6189(3) 0.0621(17) Uani 1 1 d . . . H21A H 0.0373 0.4487 0.6558 0.074 Uiso 1 1 calc R . . C22 C 0.1569(4) 0.4150(6) 0.5987(3) 0.0534(14) Uani 1 1 d . . . H22A H 0.1781 0.3471 0.6226 0.064 Uiso 1 1 calc R . . C23 C 0.2180(6) 0.5430(8) 0.3344(3) 0.085(2) Uani 1 1 d . . . H23A H 0.1667 0.5296 0.3017 0.127 Uiso 1 1 calc R . . H23B H 0.2662 0.4785 0.3321 0.127 Uiso 1 1 calc R . . H23C H 0.2500 0.6197 0.3260 0.127 Uiso 1 1 calc R . . O5 O 0.0950(11) 0.5640(14) 0.0795(7) 0.130(5) Uiso 0.50 1 d PDU . . C24 C 0.062(2) 0.539(3) 0.1517(9) 0.167(10) Uiso 0.50 1 d PDU . . O6 O 0.073(2) 0.225(3) 0.2621(15) 0.150(10) Uiso 0.25 1 d PDU A 1 C25 C 0.177(3) 0.205(4) 0.292(2) 0.104(11) Uiso 0.25 1 d PDU A 1 C25' C 0.214(4) 0.243(5) 0.2687(17) 0.143(15) Uiso 0.25 1 d PDU B 2 O6' O 0.163(2) 0.226(3) 0.3349(15) 0.130(9) Uiso 0.25 1 d PDU B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0387(4) 0.0295(4) 0.0321(4) -0.0018(2) 0.0037(3) -0.0014(2) Ni2 0.0396(4) 0.0311(4) 0.0369(4) 0.0003(3) 0.0021(3) -0.0039(3) O1 0.0393(18) 0.0298(17) 0.0289(16) 0.0001(13) 0.0052(13) -0.0003(13) O2 0.049(2) 0.073(3) 0.038(2) 0.0013(19) -0.0024(17) -0.0085(19) O3 0.0354(18) 0.0320(17) 0.0368(18) -0.0007(14) -0.0001(14) 0.0002(13) O4 0.043(2) 0.062(3) 0.044(2) 0.0004(18) -0.0048(16) -0.0006(18) N1 0.107(4) 0.116(4) 0.150(5) 0.004(4) 0.008(4) -0.008(4) N2 0.096(4) 0.079(4) 0.113(4) -0.004(3) -0.002(3) 0.003(3) N3 0.046(3) 0.046(3) 0.073(3) -0.004(2) 0.004(2) -0.014(2) N4 0.112(4) 0.104(4) 0.071(3) -0.022(3) 0.012(3) -0.029(3) N5 0.069(3) 0.053(3) 0.037(3) -0.012(2) 0.006(2) -0.018(2) N6 0.044(2) 0.036(2) 0.040(2) -0.0073(19) 0.0031(19) -0.0051(18) N7 0.051(3) 0.034(2) 0.041(2) 0.0037(18) 0.001(2) -0.0032(19) N8 0.042(2) 0.038(2) 0.034(2) -0.0066(18) 0.0080(18) -0.0027(18) N9 0.051(3) 0.033(2) 0.041(2) 0.0001(19) 0.011(2) 0.0008(19) N10 0.043(2) 0.039(2) 0.042(2) 0.0007(19) 0.0077(19) -0.0055(19) C1 0.069(4) 0.039(3) 0.063(4) 0.009(3) 0.000(3) -0.012(3) C2 0.095(5) 0.042(3) 0.077(5) 0.020(3) -0.004(4) -0.010(3) C3 0.088(5) 0.057(4) 0.060(4) 0.031(3) -0.006(4) 0.000(3) C4 0.070(4) 0.051(3) 0.049(3) 0.011(3) -0.004(3) -0.001(3) C5 0.047(3) 0.039(3) 0.032(3) 0.002(2) 0.006(2) 0.002(2) C6 0.043(3) 0.040(3) 0.032(3) 0.003(2) -0.001(2) -0.005(2) C7 0.041(3) 0.046(3) 0.031(2) -0.008(2) 0.009(2) -0.008(2) C8 0.071(4) 0.065(4) 0.040(3) 0.004(3) 0.014(3) 0.002(3) C9 0.104(6) 0.080(5) 0.044(4) -0.017(3) 0.036(4) 0.009(4) C10 0.099(5) 0.053(4) 0.061(4) -0.009(3) 0.030(4) 0.015(4) C11 0.063(4) 0.040(3) 0.052(3) -0.011(3) 0.009(3) 0.002(3) C12 0.067(4) 0.034(3) 0.061(4) 0.000(3) 0.004(3) -0.003(3) C13 0.080(5) 0.037(3) 0.076(4) 0.009(3) 0.009(4) 0.010(3) C14 0.084(5) 0.049(4) 0.075(4) 0.010(3) 0.011(4) 0.027(3) C15 0.064(4) 0.053(4) 0.058(4) 0.006(3) 0.002(3) 0.015(3) C16 0.046(3) 0.038(3) 0.044(3) 0.003(2) 0.006(2) 0.001(2) C17 0.036(3) 0.040(3) 0.038(3) 0.002(2) 0.001(2) 0.001(2) C18 0.038(3) 0.044(3) 0.046(3) 0.000(2) 0.003(2) -0.006(2) C19 0.042(3) 0.055(4) 0.060(4) -0.002(3) 0.009(3) 0.008(2) C20 0.046(3) 0.069(4) 0.081(5) -0.008(4) 0.017(3) 0.007(3) C21 0.048(4) 0.080(5) 0.058(4) -0.001(3) 0.019(3) -0.009(3) C22 0.050(3) 0.056(4) 0.054(3) 0.007(3) 0.009(3) -0.009(3) C23 0.079(5) 0.112(7) 0.063(4) -0.009(4) -0.002(4) -0.012(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 O1 2.023(3) . ? Ni1 N9 2.037(4) . ? Ni1 N6 2.072(4) . ? Ni1 O1 2.097(3) 3_666 ? Ni1 N8 2.097(4) . ? Ni1 O3 2.113(3) . ? Ni2 O3 2.037(3) . ? Ni2 N3 2.072(5) . ? Ni2 N7 2.094(4) . ? Ni2 N6 2.102(4) 3_666 ? Ni2 N10 2.110(4) . ? Ni2 O1 2.138(3) . ? O1 C6 1.387(5) . ? O1 Ni1 2.097(3) 3_666 ? O2 C6 1.423(6) . ? O2 H2A 0.8200 . ? O3 C17 1.367(6) . ? O4 C23 1.377(8) . ? O4 C17 1.432(6) . ? N1 N2 1.286(11) . ? N2 N3 1.163(9) . ? N4 N5 1.144(7) . ? N5 N6 1.190(6) . ? N6 Ni2 2.102(4) 3_666 ? N7 C5 1.329(6) . ? N7 C1 1.340(7) . ? N8 C11 1.340(7) . ? N8 C7 1.358(6) . ? N9 C16 1.327(7) . ? N9 C12 1.350(7) . ? N10 C22 1.332(7) . ? N10 C18 1.338(7) . ? C1 C2 1.351(8) . ? C1 H1A 0.9300 . ? C2 C3 1.372(9) . ? C2 H2B 0.9300 . ? C3 C4 1.368(8) . ? C3 H3B 0.9300 . ? C4 C5 1.399(7) . ? C4 H4A 0.9300 . ? C5 C6 1.528(7) . ? C6 C7 1.541(7) . ? C7 C8 1.371(7) . ? C8 C9 1.387(9) . ? C8 H8A 0.9300 . ? C9 C10 1.343(9) . ? C9 H9A 0.9300 . ? C10 C11 1.366(8) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 C13 1.361(8) . ? C12 H12A 0.9300 . ? C13 C14 1.367(9) . ? C13 H13A 0.9300 . ? C14 C15 1.409(9) . ? C14 H14A 0.9300 . ? C15 C16 1.393(8) . ? C15 H15A 0.9300 . ? C16 C17 1.538(7) . ? C17 C18 1.550(7) . ? C18 C19 1.372(7) . ? C19 C20 1.348(9) . ? C19 H19A 0.9300 . ? C20 C21 1.367(9) . ? C20 H20A 0.9300 . ? C21 C22 1.378(8) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? O5 C24 1.550(10) . ? O6 C25 1.536(10) . ? C25' O6' 1.518(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 O1 Ni1 N9 158.77(16) . . ? O1 Ni1 N6 102.67(14) . . ? N9 Ni1 N6 98.18(17) . . ? O1 Ni1 O1 80.95(13) . 3_666 ? N9 Ni1 O1 107.23(14) . 3_666 ? N6 Ni1 O1 78.86(14) . 3_666 ? O1 Ni1 N8 77.94(14) . . ? N9 Ni1 N8 97.67(16) . . ? N6 Ni1 N8 91.58(16) . . ? O1 Ni1 N8 154.29(15) 3_666 . ? O1 Ni1 O3 83.33(12) . . ? N9 Ni1 O3 77.68(15) . . ? N6 Ni1 O3 163.61(14) . . ? O1 Ni1 O3 87.17(12) 3_666 . ? N8 Ni1 O3 104.65(14) . . ? O3 Ni2 N3 103.13(17) . . ? O3 Ni2 N7 155.58(14) . . ? N3 Ni2 N7 100.00(18) . . ? O3 Ni2 N6 92.31(14) . 3_666 ? N3 Ni2 N6 90.48(18) . 3_666 ? N7 Ni2 N6 95.24(17) . 3_666 ? O3 Ni2 N10 77.52(14) . . ? N3 Ni2 N10 89.34(18) . . ? N7 Ni2 N10 95.13(17) . . ? N6 Ni2 N10 169.50(17) 3_666 . ? O3 Ni2 O1 82.38(12) . . ? N3 Ni2 O1 166.87(17) . . ? N7 Ni2 O1 76.72(14) . . ? N6 Ni2 O1 77.29(14) 3_666 . ? N10 Ni2 O1 103.56(14) . . ? C6 O1 Ni1 117.5(3) . . ? C6 O1 Ni1 128.7(3) . 3_666 ? Ni1 O1 Ni1 99.05(13) . 3_666 ? C6 O1 Ni2 109.9(3) . . ? Ni1 O1 Ni2 95.36(13) . . ? Ni1 O1 Ni2 100.39(12) 3_666 . ? C6 O2 H2A 109.5 . . ? C17 O3 Ni2 117.1(3) . . ? C17 O3 Ni1 107.8(3) . . ? Ni2 O3 Ni1 95.73(12) . . ? C23 O4 C17 116.8(4) . . ? N3 N2 N1 178.5(9) . . ? N2 N3 Ni2 124.3(5) . . ? N4 N5 N6 178.5(7) . . ? N5 N6 Ni1 125.9(4) . . ? N5 N6 Ni2 126.6(4) . 3_666 ? Ni1 N6 Ni2 102.42(17) . 3_666 ? C5 N7 C1 118.4(5) . . ? C5 N7 Ni2 114.8(3) . . ? C1 N7 Ni2 126.7(4) . . ? C11 N8 C7 118.2(4) . . ? C11 N8 Ni1 127.1(4) . . ? C7 N8 Ni1 114.5(3) . . ? C16 N9 C12 118.9(5) . . ? C16 N9 Ni1 114.1(3) . . ? C12 N9 Ni1 126.9(4) . . ? C22 N10 C18 117.7(5) . . ? C22 N10 Ni2 126.5(4) . . ? C18 N10 Ni2 115.5(3) . . ? N7 C1 C2 123.2(6) . . ? N7 C1 H1A 118.4 . . ? C2 C1 H1A 118.4 . . ? C1 C2 C3 118.2(6) . . ? C1 C2 H2B 120.9 . . ? C3 C2 H2B 120.9 . . ? C4 C3 C2 120.6(6) . . ? C4 C3 H3B 119.7 . . ? C2 C3 H3B 119.7 . . ? C3 C4 C5 117.5(6) . . ? C3 C4 H4A 121.2 . . ? C5 C4 H4A 121.2 . . ? N7 C5 C4 122.0(5) . . ? N7 C5 C6 115.7(4) . . ? C4 C5 C6 122.4(5) . . ? O1 C6 O2 112.7(4) . . ? O1 C6 C5 108.6(4) . . ? O2 C6 C5 109.0(4) . . ? O1 C6 C7 108.9(4) . . ? O2 C6 C7 105.5(4) . . ? C5 C6 C7 112.2(4) . . ? N8 C7 C8 121.6(5) . . ? N8 C7 C6 115.4(4) . . ? C8 C7 C6 122.9(5) . . ? C7 C8 C9 117.9(6) . . ? C7 C8 H8A 121.0 . . ? C9 C8 H8A 121.0 . . ? C10 C9 C8 120.8(6) . . ? C10 C9 H9A 119.6 . . ? C8 C9 H9A 119.6 . . ? C9 C10 C11 118.7(6) . . ? C9 C10 H10A 120.6 . . ? C11 C10 H10A 120.6 . . ? N8 C11 C10 122.6(6) . . ? N8 C11 H11A 118.7 . . ? C10 C11 H11A 118.7 . . ? N9 C12 C13 122.8(6) . . ? N9 C12 H12A 118.6 . . ? C13 C12 H12A 118.6 . . ? C12 C13 C14 118.8(6) . . ? C12 C13 H13A 120.6 . . ? C14 C13 H13A 120.6 . . ? C13 C14 C15 120.0(6) . . ? C13 C14 H14A 120.0 . . ? C15 C14 H14A 120.0 . . ? C16 C15 C14 117.1(6) . . ? C16 C15 H15A 121.4 . . ? C14 C15 H15A 121.4 . . ? N9 C16 C15 122.4(5) . . ? N9 C16 C17 114.9(4) . . ? C15 C16 C17 122.7(5) . . ? O3 C17 O4 113.5(4) . . ? O3 C17 C16 109.1(4) . . ? O4 C17 C16 108.7(4) . . ? O3 C17 C18 110.6(4) . . ? O4 C17 C18 102.9(4) . . ? C16 C17 C18 111.9(4) . . ? N10 C18 C19 121.9(5) . . ? N10 C18 C17 114.2(4) . . ? C19 C18 C17 123.8(5) . . ? C20 C19 C18 119.7(6) . . ? C20 C19 H19A 120.2 . . ? C18 C19 H19A 120.2 . . ? C19 C20 C21 119.7(6) . . ? C19 C20 H20A 120.2 . . ? C21 C20 H20A 120.2 . . ? C20 C21 C22 118.1(6) . . ? C20 C21 H21A 121.0 . . ? C22 C21 H21A 121.0 . . ? N10 C22 C21 123.0(6) . . ? N10 C22 H22A 118.5 . . ? C21 C22 H22A 118.5 . . ? O4 C23 H23A 109.5 . . ? O4 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O4 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.933 _refine_diff_density_min -0.646 _refine_diff_density_rms 0.150 # Attachment 'compound 2.cif' data_a _database_code_depnum_ccdc_archive 'CCDC 631555' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H44 Cl4 Cu6 N14 O8' _chemical_formula_weight 1468.01 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 Tetragonal _symmetry_space_group_name_H-M I4(1)/acd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+1/4, x+3/4, z+1/4' 'y+1/4, -x+1/4, z+3/4' '-x+1/2, y, -z' 'x, -y, -z+1/2' 'y+1/4, x+3/4, -z+3/4' '-y+1/4, -x+1/4, -z+1/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+3/4, x+5/4, z+3/4' 'y+3/4, -x+3/4, z+5/4' '-x+1, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1' 'y+3/4, x+5/4, -z+5/4' '-y+3/4, -x+3/4, -z+3/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-1/4, -x-3/4, -z-1/4' '-y-1/4, x-1/4, -z-3/4' 'x-1/2, -y, z' '-x, y, z-1/2' '-y-1/4, -x-3/4, z-3/4' 'y-1/4, x-1/4, z-1/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y+1/4, -x-1/4, -z+1/4' '-y+1/4, x+1/4, -z-1/4' 'x, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' '-y+1/4, -x-1/4, z-1/4' 'y+1/4, x+1/4, z+1/4' _cell_length_a 15.491(2) _cell_length_b 15.491(2) _cell_length_c 45.272(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 10865(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour dark-blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.795 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5888 _exptl_absorpt_coefficient_mu 2.570 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.601 _exptl_absorpt_correction_T_max 0.402 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 25000 _diffrn_reflns_av_R_equivalents 0.0587 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -53 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2401 _reflns_number_gt 1738 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2401 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0853 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 0.7500 0.683906(11) 0.02930(16) Uani 1 2 d S . . Cu2 Cu 0.42703(2) 0.82297(2) 0.6250 0.02768(16) Uani 1 2 d S . . O1 O 0.39079(14) 0.95030(13) 0.70885(4) 0.0411(6) Uani 1 1 d . . . O2 O 0.41733(12) 0.83722(12) 0.67662(4) 0.0297(5) Uani 1 1 d . . . N1 N 0.57664(16) 0.84599(15) 0.69359(5) 0.0325(6) Uani 1 1 d . . . N2 N 0.42421(15) 0.95198(15) 0.63237(5) 0.0299(6) Uani 1 1 d . . . N3 N 0.55582(13) 0.80582(13) 0.6250 0.0198(7) Uani 1 2 d S . . N4 N 0.6118(2) 0.8618(2) 0.6250 0.0507(11) Uani 1 2 d S . . N5 N 0.6613(4) 0.9113(4) 0.6250 0.158(4) Uani 1 2 d S . . C1 C 0.6601(2) 0.8421(2) 0.70092(8) 0.0451(9) Uani 1 1 d . . . H1A H 0.6874 0.7886 0.7011 0.054 Uiso 1 1 calc R . . C2 C 0.7070(2) 0.9141(2) 0.70817(9) 0.0563(10) Uani 1 1 d . . . H2A H 0.7654 0.9102 0.7127 0.068 Uiso 1 1 calc R . . C3 C 0.6649(3) 0.9922(2) 0.70856(9) 0.0582(10) Uani 1 1 d . . . H3A H 0.6946 1.0420 0.7138 0.070 Uiso 1 1 calc R . . C4 C 0.5794(2) 0.9967(2) 0.70127(7) 0.0446(8) Uani 1 1 d . . . H4A H 0.5506 1.0494 0.7015 0.054 Uiso 1 1 calc R . . C5 C 0.53644(19) 0.92234(18) 0.69351(6) 0.0320(7) Uani 1 1 d . . . C6 C 0.44039(19) 0.91868(18) 0.68475(6) 0.0307(7) Uani 1 1 d . . . C7 C 0.3923(3) 0.8952(2) 0.73406(8) 0.0585(10) Uani 1 1 d . . . H7A H 0.3576 0.9199 0.7495 0.088 Uiso 1 1 calc R . . H7B H 0.4506 0.8889 0.7409 0.088 Uiso 1 1 calc R . . H7C H 0.3697 0.8395 0.7288 0.088 Uiso 1 1 calc R . . C8 C 0.42298(18) 0.98275(18) 0.66002(6) 0.0306(7) Uani 1 1 d . . . C9 C 0.4063(2) 1.06862(19) 0.66538(8) 0.0415(8) Uani 1 1 d . . . H9A H 0.4054 1.0893 0.6847 0.050 Uiso 1 1 calc R . . C10 C 0.3909(2) 1.1238(2) 0.64220(8) 0.0491(9) Uani 1 1 d . . . H10A H 0.3795 1.1819 0.6456 0.059 Uiso 1 1 calc R . . C11 C 0.3927(2) 1.0919(2) 0.61404(8) 0.0464(9) Uani 1 1 d . . . H11A H 0.3824 1.1279 0.5980 0.056 Uiso 1 1 calc R . . C12 C 0.4098(2) 1.0062(2) 0.60997(7) 0.0379(7) Uani 1 1 d . . . H12A H 0.4115 0.9848 0.5908 0.046 Uiso 1 1 calc R . . Cu3 Cu 1.0000 0.7500 0.712106(17) 0.0636(2) Uani 1 2 d S . . Cl1 Cl 0.86771(7) 0.72788(7) 0.71165(3) 0.0800(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0307(3) 0.0224(3) 0.0348(3) 0.000 0.000 0.0027(2) Cu2 0.0258(2) 0.0258(2) 0.0314(3) -0.00100(16) -0.00100(16) 0.0026(2) O1 0.0542(14) 0.0350(12) 0.0343(13) -0.0020(10) 0.0118(11) 0.0112(10) O2 0.0292(11) 0.0226(11) 0.0374(12) -0.0005(9) -0.0001(9) 0.0017(9) N1 0.0325(14) 0.0299(14) 0.0350(15) -0.0016(11) -0.0030(11) 0.0001(11) N2 0.0286(13) 0.0278(13) 0.0334(15) 0.0020(11) 0.0007(11) 0.0024(11) N3 0.0156(10) 0.0156(10) 0.0281(18) -0.0013(10) 0.0013(10) 0.0003(13) N4 0.0513(17) 0.0513(17) 0.049(3) -0.0028(14) 0.0028(14) 0.004(2) N5 0.155(5) 0.155(5) 0.163(9) 0.000(4) 0.000(4) -0.040(7) C1 0.0381(19) 0.043(2) 0.055(2) -0.0006(17) -0.0130(17) 0.0029(17) C2 0.043(2) 0.060(3) 0.066(3) 0.001(2) -0.017(2) -0.0077(18) C3 0.067(3) 0.043(2) 0.064(3) -0.0015(19) -0.021(2) -0.022(2) C4 0.054(2) 0.0291(17) 0.051(2) -0.0029(15) -0.0110(17) -0.0026(15) C5 0.0392(18) 0.0282(16) 0.0286(16) -0.0016(13) -0.0002(14) 0.0006(14) C6 0.0366(18) 0.0251(16) 0.0303(17) -0.0027(13) 0.0031(13) 0.0029(13) C7 0.085(3) 0.057(2) 0.034(2) 0.0019(18) 0.0180(19) 0.011(2) C8 0.0290(16) 0.0275(16) 0.0354(18) -0.0008(13) 0.0025(13) 0.0025(13) C9 0.050(2) 0.0297(17) 0.045(2) -0.0047(15) -0.0011(16) 0.0074(15) C10 0.061(2) 0.0283(18) 0.058(3) 0.0044(17) 0.0022(19) 0.0112(16) C11 0.050(2) 0.0370(19) 0.052(2) 0.0134(17) -0.0059(18) 0.0042(16) C12 0.0411(19) 0.0359(18) 0.0368(18) 0.0041(15) -0.0015(15) -0.0010(14) Cu3 0.0874(5) 0.0445(4) 0.0589(5) 0.000 0.000 0.0126(3) Cl1 0.0890(8) 0.0602(7) 0.0909(9) -0.0114(6) -0.0130(7) 0.0090(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.8906(19) 10_564 ? Cu1 O2 1.8906(19) . ? Cu1 N1 1.953(2) . ? Cu1 N1 1.953(2) 10_564 ? Cu2 N3 2.0127(19) . ? Cu2 N3 2.0127(19) 10_564 ? Cu2 N2 2.027(2) . ? Cu2 N2 2.027(2) 8_666 ? Cu2 O2 2.352(2) . ? Cu2 O2 2.352(2) 8_666 ? O1 C6 1.422(3) . ? O1 C7 1.426(4) . ? O2 C6 1.362(3) . ? N1 C1 1.336(4) . ? N1 C5 1.337(3) . ? N2 C12 1.336(4) . ? N2 C8 1.340(4) . ? N3 N4 1.226(6) . ? N3 Cu2 2.0127(19) 10_564 ? N4 N5 1.084(9) . ? C1 C2 1.371(5) . ? C1 H1A 0.9300 . ? C2 C3 1.376(5) . ? C2 H2A 0.9300 . ? C3 C4 1.367(5) . ? C3 H3A 0.9300 . ? C4 C5 1.376(4) . ? C4 H4A 0.9300 . ? C5 C6 1.541(4) . ? C6 C8 1.520(4) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.377(4) . ? C9 C10 1.374(4) . ? C9 H9A 0.9300 . ? C10 C11 1.368(5) . ? C10 H10A 0.9300 . ? C11 C12 1.366(4) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? Cu3 Cl1 2.0779(12) 10_664 ? Cu3 Cl1 2.0779(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 O2 159.91(12) 10_564 . ? O2 Cu1 N1 99.88(9) 10_564 . ? O2 Cu1 N1 84.65(9) . . ? O2 Cu1 N1 84.65(9) 10_564 10_564 ? O2 Cu1 N1 99.88(9) . 10_564 ? N1 Cu1 N1 154.04(15) . 10_564 ? N3 Cu2 N3 74.83(13) . 10_564 ? N3 Cu2 N2 98.72(9) . . ? N3 Cu2 N2 168.62(8) 10_564 . ? N3 Cu2 N2 168.62(8) . 8_666 ? N3 Cu2 N2 98.72(9) 10_564 8_666 ? N2 Cu2 N2 89.12(13) . 8_666 ? N3 Cu2 O2 94.34(5) . . ? N3 Cu2 O2 95.82(5) 10_564 . ? N2 Cu2 O2 75.08(8) . . ? N2 Cu2 O2 95.65(8) 8_666 . ? N3 Cu2 O2 95.82(5) . 8_666 ? N3 Cu2 O2 94.34(5) 10_564 8_666 ? N2 Cu2 O2 95.65(8) . 8_666 ? N2 Cu2 O2 75.08(8) 8_666 8_666 ? O2 Cu2 O2 167.19(9) . 8_666 ? C6 O1 C7 113.5(2) . . ? C6 O2 Cu1 115.93(17) . . ? C6 O2 Cu2 109.79(16) . . ? Cu1 O2 Cu2 93.61(8) . . ? C1 N1 C5 119.5(3) . . ? C1 N1 Cu1 127.5(2) . . ? C5 N1 Cu1 112.95(19) . . ? C12 N2 C8 118.9(3) . . ? C12 N2 Cu2 120.0(2) . . ? C8 N2 Cu2 120.33(19) . . ? N4 N3 Cu2 127.41(7) . . ? N4 N3 Cu2 127.41(7) . 10_564 ? Cu2 N3 Cu2 105.17(13) . 10_564 ? N5 N4 N3 180.0(5) . . ? N1 C1 C2 122.3(3) . . ? N1 C1 H1A 118.8 . . ? C2 C1 H1A 118.8 . . ? C1 C2 C3 117.9(3) . . ? C1 C2 H2A 121.1 . . ? C3 C2 H2A 121.1 . . ? C4 C3 C2 120.1(3) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C3 C4 C5 119.1(3) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? N1 C5 C4 121.0(3) . . ? N1 C5 C6 114.7(2) . . ? C4 C5 C6 124.3(3) . . ? O2 C6 O1 112.6(2) . . ? O2 C6 C8 111.1(2) . . ? O1 C6 C8 104.1(2) . . ? O2 C6 C5 110.9(2) . . ? O1 C6 C5 108.2(2) . . ? C8 C6 C5 109.7(2) . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 C9 120.7(3) . . ? N2 C8 C6 117.0(2) . . ? C9 C8 C6 122.3(3) . . ? C10 C9 C8 120.0(3) . . ? C10 C9 H9A 120.0 . . ? C8 C9 H9A 120.0 . . ? C11 C10 C9 118.9(3) . . ? C11 C10 H10A 120.5 . . ? C9 C10 H10A 120.5 . . ? C12 C11 C10 118.7(3) . . ? C12 C11 H11A 120.6 . . ? C10 C11 H11A 120.6 . . ? N2 C12 C11 122.8(3) . . ? N2 C12 H12A 118.6 . . ? C11 C12 H12A 118.6 . . ? Cl1 Cu3 Cl1 178.85(8) 10_664 . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.560 _refine_diff_density_min -0.593 _refine_diff_density_rms 0.075 data_a _database_code_depnum_ccdc_archive 'CCDC 631556' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H24 Cl3 Cu2 N7 O5' _chemical_formula_weight 747.95 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.544(3) _cell_length_b 12.379(3) _cell_length_c 13.988(3) _cell_angle_alpha 64.968(4) _cell_angle_beta 68.102(4) _cell_angle_gamma 73.782(4) _cell_volume 1519.0(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 572 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 23.42 _exptl_crystal_description block _exptl_crystal_colour dark-blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 1.713 _exptl_absorpt_correction_type multis-scan _exptl_absorpt_correction_T_min 0.602 _exptl_absorpt_correction_T_max 0.725 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 7611 _diffrn_reflns_av_R_equivalents 0.0668 _diffrn_reflns_av_sigmaI/netI 0.0672 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5271 _reflns_number_gt 3924 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0850P)^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 5271 _refine_ls_number_parameters 437 _refine_ls_number_restraints 710 _refine_ls_R_factor_all 0.0699 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1491 _refine_ls_wR_factor_gt 0.1415 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.29625(8) 0.74052(6) 0.29985(6) 0.0676(3) Uani 1 1 d . . . Cu2 Cu 0.35252(5) 0.45475(5) 0.13807(4) 0.0424(2) Uani 1 1 d . A . Cl1 Cl 0.3207(16) 0.8228(7) 0.4015(9) 0.091(2) Uani 0.61(3) 1 d PU A 1 Cl1' Cl 0.397(3) 0.8363(8) 0.3556(18) 0.094(4) Uani 0.39(3) 1 d PU A 2 Cl2 Cl 0.44649(12) 0.36187(11) 0.01488(10) 0.0510(3) Uani 1 1 d . . . O1 O 0.4677(4) 0.5400(3) 0.3257(3) 0.0595(8) Uani 1 1 d U . . N1 N 0.2174(5) 0.6050(4) 0.4351(3) 0.0718(12) Uani 1 1 d U A . N2 N 0.4286(4) 0.3231(3) 0.2551(3) 0.0524(9) Uani 1 1 d U A . N3 N 0.3125(4) 0.5386(3) 0.2368(3) 0.0423(8) Uani 1 1 d U . . N4 N 0.2916(4) 0.6577(3) 0.2063(3) 0.0419(8) Uani 1 1 d U A . N5 N 0.3013(4) 0.8788(3) 0.1595(3) 0.0522(9) Uani 1 1 d U A . N6 N 0.2272(4) 0.5823(3) 0.0577(3) 0.0422(8) Uani 1 1 d U . . C1 C 0.1196(8) 0.6224(6) 0.5232(5) 0.096(2) Uani 1 1 d U . . H1A H 0.0940 0.7004 0.5239 0.115 Uiso 1 1 calc R A . C2 C 0.0558(8) 0.5347(7) 0.6106(5) 0.102(2) Uani 1 1 d U A . H2A H -0.0106 0.5521 0.6703 0.123 Uiso 1 1 calc R . . C3 C 0.0893(8) 0.4202(7) 0.6112(5) 0.099(2) Uani 1 1 d U . . H3A H 0.0459 0.3580 0.6706 0.119 Uiso 1 1 calc R A . C4 C 0.1906(6) 0.3985(6) 0.5202(4) 0.0767(16) Uani 1 1 d U A . H4A H 0.2154 0.3212 0.5180 0.092 Uiso 1 1 calc R . . C5 C 0.2525(6) 0.4910(5) 0.4351(4) 0.0617(12) Uani 1 1 d U . . C6 C 0.3668(5) 0.4803(4) 0.3327(4) 0.0480(10) Uani 1 1 d U A . C7 C 0.4252(5) 0.3511(4) 0.3392(4) 0.0498(10) Uani 1 1 d U . . C8 C 0.4828(6) 0.2714(4) 0.4199(4) 0.0622(13) Uani 1 1 d U A . H8A H 0.4816 0.2929 0.4764 0.075 Uiso 1 1 calc R . . C9 C 0.5430(6) 0.1581(5) 0.4168(5) 0.0715(14) Uani 1 1 d U . . H9A H 0.5832 0.1030 0.4713 0.086 Uiso 1 1 calc R A . C10 C 0.5438(7) 0.1271(5) 0.3346(5) 0.0739(15) Uani 1 1 d U A . H10A H 0.5825 0.0506 0.3323 0.089 Uiso 1 1 calc R . . C11 C 0.4860(6) 0.2114(5) 0.2553(5) 0.0665(13) Uani 1 1 d U . . H11A H 0.4864 0.1906 0.1986 0.080 Uiso 1 1 calc R A . C12 C 0.3266(6) 0.9893(5) 0.1340(5) 0.0625(13) Uani 1 1 d U . . H12A H 0.3466 1.0053 0.1857 0.075 Uiso 1 1 calc R A . C13 C 0.3242(6) 1.0797(5) 0.0349(5) 0.0707(14) Uani 1 1 d U A . H13A H 0.3395 1.1563 0.0205 0.085 Uiso 1 1 calc R . . C14 C 0.2991(6) 1.0558(5) -0.0415(5) 0.0688(14) Uani 1 1 d U . . H14A H 0.3006 1.1149 -0.1106 0.083 Uiso 1 1 calc R A . C15 C 0.2713(5) 0.9428(4) -0.0160(4) 0.0575(12) Uani 1 1 d U A . H15A H 0.2533 0.9254 -0.0678 0.069 Uiso 1 1 calc R . . C16 C 0.2701(5) 0.8555(4) 0.0863(4) 0.0462(10) Uani 1 1 d U . . C17 C 0.2493(4) 0.7306(4) 0.1211(4) 0.0433(10) Uani 1 1 d U A . C18 C 0.1883(4) 0.6936(4) 0.0618(4) 0.0430(10) Uani 1 1 d U A . C19 C 0.0871(5) 0.7735(4) 0.0159(4) 0.0530(11) Uani 1 1 d U . . H19A H 0.0559 0.8477 0.0248 0.064 Uiso 1 1 calc R A . C20 C 0.0328(5) 0.7425(5) -0.0427(5) 0.0627(13) Uani 1 1 d U A . H20A H -0.0332 0.7964 -0.0760 0.075 Uiso 1 1 calc R . . C21 C 0.0772(5) 0.6307(5) -0.0516(4) 0.0593(12) Uani 1 1 d U . . H21A H 0.0444 0.6086 -0.0930 0.071 Uiso 1 1 calc R A . C22 C 0.1706(5) 0.5528(4) 0.0016(4) 0.0519(11) Uani 1 1 d U A . H22A H 0.1965 0.4756 -0.0009 0.062 Uiso 1 1 calc R . . C23 C 0.5978(7) 0.5279(6) 0.2515(5) 0.0794(16) Uani 1 1 d U . . H23A H 0.5878 0.5341 0.1831 0.095 Uiso 1 1 calc R . . H23B H 0.6480 0.4491 0.2817 0.095 Uiso 1 1 calc R . . C24 C 0.6745(10) 0.6196(8) 0.2294(8) 0.138(3) Uani 1 1 d U . . H24A H 0.7666 0.6053 0.1836 0.207 Uiso 1 1 calc R . . H24B H 0.6782 0.6175 0.2977 0.207 Uiso 1 1 calc R . . H24C H 0.6299 0.6972 0.1922 0.207 Uiso 1 1 calc R . . C25 C 0.1049(11) 0.1044(8) 0.3848(8) 0.149(3) Uani 1 1 d U . . H25A H 0.0187 0.0791 0.4010 0.224 Uiso 1 1 calc R . . H25B H 0.1070 0.1168 0.4474 0.224 Uiso 1 1 calc R . . H25C H 0.1796 0.0434 0.3686 0.224 Uiso 1 1 calc R . . C26 C 0.1187(8) 0.2129(7) 0.2928(6) 0.094(2) Uani 1 1 d U . . N7 N 0.1343(7) 0.2985(6) 0.2256(5) 0.1040(19) Uani 1 1 d U . . Cl3 Cl -0.0890(2) 0.92098(18) 0.29358(16) 0.1035(7) Uani 1 1 d DU . . O11 O -0.2200(9) 0.8944(11) 0.3555(11) 0.141(4) Uani 0.557(8) 1 d PDU B 1 O12 O -0.0839(13) 1.0399(8) 0.2947(11) 0.146(4) Uani 0.557(8) 1 d PDU B 1 O13 O -0.0488(12) 0.9404(11) 0.1818(6) 0.131(3) Uani 0.557(8) 1 d PDU B 1 O14 O 0.0155(11) 0.8473(10) 0.3451(9) 0.112(3) Uani 0.557(8) 1 d PDU B 1 O11' O -0.1831(12) 0.9227(12) 0.3971(8) 0.110(3) Uani 0.443(8) 1 d PDU B 2 O12' O -0.0415(16) 1.0205(11) 0.2114(12) 0.155(4) Uani 0.443(8) 1 d PDU B 2 O13' O -0.1771(15) 0.8782(12) 0.2593(12) 0.139(4) Uani 0.443(8) 1 d PDU B 2 O14' O 0.0117(14) 0.8157(11) 0.3173(13) 0.119(4) Uani 0.443(8) 1 d PDU B 2 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 0.1034(6) 0.0470(4) 0.0726(5) -0.0323(3) -0.0541(4) 0.0162(4) Cu2 0.0463(3) 0.0394(3) 0.0453(3) -0.0204(2) -0.0197(3) 0.0051(2) Cl1 0.141(6) 0.071(2) 0.093(4) -0.043(3) -0.068(4) 0.005(3) Cl1' 0.159(11) 0.061(3) 0.106(8) -0.034(4) -0.093(8) 0.002(4) Cl2 0.0545(7) 0.0506(7) 0.0550(7) -0.0298(6) -0.0122(5) -0.0058(5) O1 0.070(2) 0.0523(19) 0.066(2) -0.0272(16) -0.0306(17) 0.0027(16) N1 0.098(3) 0.063(2) 0.047(2) -0.0272(19) -0.031(2) 0.023(2) N2 0.061(2) 0.040(2) 0.061(2) -0.0214(17) -0.0313(18) 0.0104(17) N3 0.0513(19) 0.0357(18) 0.0410(18) -0.0171(14) -0.0186(15) 0.0047(15) N4 0.0445(19) 0.0372(18) 0.0448(19) -0.0185(15) -0.0162(16) 0.0033(15) N5 0.057(2) 0.040(2) 0.071(2) -0.0245(18) -0.0302(19) 0.0002(17) N6 0.0438(18) 0.0390(19) 0.047(2) -0.0152(16) -0.0187(16) -0.0040(15) C1 0.118(4) 0.084(4) 0.061(3) -0.035(3) -0.027(3) 0.037(3) C2 0.117(4) 0.101(4) 0.054(3) -0.031(3) -0.015(3) 0.029(4) C3 0.109(4) 0.099(4) 0.053(3) -0.017(3) -0.019(3) 0.015(3) C4 0.092(4) 0.074(3) 0.047(3) -0.020(2) -0.022(3) 0.011(3) C5 0.079(3) 0.060(3) 0.044(2) -0.024(2) -0.029(2) 0.017(2) C6 0.058(2) 0.044(2) 0.047(2) -0.0213(18) -0.0240(19) 0.0058(19) C7 0.059(2) 0.043(2) 0.053(2) -0.0219(19) -0.026(2) 0.0051(19) C8 0.080(3) 0.048(3) 0.063(3) -0.020(2) -0.037(2) 0.009(2) C9 0.092(3) 0.048(3) 0.073(3) -0.016(2) -0.048(3) 0.016(2) C10 0.096(3) 0.049(3) 0.080(3) -0.027(2) -0.048(3) 0.022(3) C11 0.091(3) 0.050(3) 0.070(3) -0.033(2) -0.041(3) 0.016(2) C12 0.067(3) 0.050(3) 0.084(3) -0.033(2) -0.031(3) -0.004(2) C13 0.074(3) 0.045(3) 0.099(4) -0.026(3) -0.031(3) -0.008(2) C14 0.075(3) 0.045(3) 0.079(3) -0.015(2) -0.025(3) -0.005(2) C15 0.067(3) 0.038(2) 0.070(3) -0.019(2) -0.027(2) -0.002(2) C16 0.045(2) 0.038(2) 0.060(2) -0.0218(19) -0.0212(19) 0.0034(18) C17 0.043(2) 0.039(2) 0.049(2) -0.0171(17) -0.0177(18) 0.0022(17) C18 0.042(2) 0.039(2) 0.046(2) -0.0118(18) -0.0153(18) -0.0050(17) C19 0.054(2) 0.041(2) 0.062(3) -0.012(2) -0.027(2) 0.000(2) C20 0.058(3) 0.055(3) 0.076(3) -0.011(2) -0.040(2) -0.001(2) C21 0.065(3) 0.057(3) 0.067(3) -0.015(2) -0.037(2) -0.012(2) C22 0.055(2) 0.046(2) 0.064(3) -0.018(2) -0.027(2) -0.010(2) C23 0.078(4) 0.082(4) 0.081(4) -0.025(3) -0.028(3) -0.015(3) C24 0.130(7) 0.123(7) 0.178(8) -0.063(6) -0.027(6) -0.056(6) C25 0.160(5) 0.120(5) 0.133(5) -0.043(4) -0.017(4) -0.009(4) C26 0.116(5) 0.072(4) 0.066(4) -0.023(4) -0.001(4) -0.009(4) N7 0.094(4) 0.101(5) 0.090(4) -0.024(4) -0.011(3) -0.013(4) Cl3 0.0892(12) 0.0860(12) 0.0836(12) -0.0104(9) -0.0187(10) 0.0219(10) O11 0.121(5) 0.125(5) 0.140(5) -0.033(4) -0.028(4) 0.000(4) O12 0.158(5) 0.129(5) 0.137(5) -0.050(4) -0.035(4) -0.010(4) O13 0.152(6) 0.151(7) 0.093(5) -0.047(5) -0.061(5) 0.014(6) O14 0.105(5) 0.122(6) 0.094(5) -0.033(5) -0.050(4) 0.023(5) O11' 0.115(6) 0.120(6) 0.102(6) -0.064(5) -0.034(5) 0.014(6) O12' 0.156(5) 0.140(5) 0.141(5) -0.037(4) -0.035(4) -0.013(4) O13' 0.152(7) 0.149(8) 0.124(7) -0.035(6) -0.078(6) -0.007(7) O14' 0.109(5) 0.115(5) 0.115(5) -0.033(4) -0.038(4) 0.005(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N5 1.979(4) . ? Cu1 N4 1.993(4) . ? Cu1 N1 2.001(5) . ? Cu1 Cl1 2.184(5) . ? Cu1 Cl1' 2.288(10) . ? Cu2 N3 1.922(4) . ? Cu2 N6 1.986(3) . ? Cu2 N2 1.992(4) . ? Cu2 Cl2 2.2450(13) . ? O1 C23 1.392(7) . ? O1 C6 1.410(6) . ? N1 C1 1.334(7) . ? N1 C5 1.356(7) . ? N2 C11 1.346(6) . ? N2 C7 1.346(6) . ? N3 N4 1.328(5) . ? N3 C6 1.473(5) . ? N4 C17 1.303(5) . ? N5 C12 1.338(6) . ? N5 C16 1.339(6) . ? N6 C18 1.343(5) . ? N6 C22 1.348(5) . ? C1 C2 1.341(10) . ? C1 H1A 0.9300 . ? C2 C3 1.360(10) . ? C2 H2A 0.9300 . ? C3 C4 1.395(8) . ? C3 H3A 0.9300 . ? C4 C5 1.355(8) . ? C4 H4A 0.9300 . ? C5 C6 1.519(7) . ? C6 C7 1.520(6) . ? C7 C8 1.361(6) . ? C8 C9 1.380(7) . ? C8 H8A 0.9300 . ? C9 C10 1.354(7) . ? C9 H9A 0.9300 . ? C10 C11 1.364(7) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 C13 1.368(8) . ? C12 H12A 0.9300 . ? C13 C14 1.350(8) . ? C13 H13A 0.9300 . ? C14 C15 1.378(7) . ? C14 H14A 0.9300 . ? C15 C16 1.379(7) . ? C15 H15A 0.9300 . ? C16 C17 1.467(6) . ? C17 C18 1.482(6) . ? C18 C19 1.383(6) . ? C19 C20 1.375(7) . ? C19 H19A 0.9300 . ? C20 C21 1.375(7) . ? C20 H20A 0.9300 . ? C21 C22 1.364(6) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? C23 C24 1.438(9) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.410(10) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 N7 1.083(8) . ? Cl3 O12' 1.344(8) . ? Cl3 O11 1.374(8) . ? Cl3 O13 1.388(7) . ? Cl3 O11' 1.423(8) . ? Cl3 O14 1.429(7) . ? Cl3 O14' 1.435(8) . ? Cl3 O13' 1.482(8) . ? Cl3 O12 1.496(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 Cu1 N4 79.98(15) . . ? N5 Cu1 N1 156.90(19) . . ? N4 Cu1 N1 89.65(17) . . ? N5 Cu1 Cl1 101.6(3) . . ? N4 Cu1 Cl1 174.7(3) . . ? N1 Cu1 Cl1 90.5(4) . . ? N5 Cu1 Cl1' 91.3(4) . . ? N4 Cu1 Cl1' 154.9(8) . . ? N1 Cu1 Cl1' 106.0(5) . . ? Cl1 Cu1 Cl1' 21.1(3) . . ? N3 Cu2 N6 90.02(14) . . ? N3 Cu2 N2 81.32(15) . . ? N6 Cu2 N2 163.43(16) . . ? N3 Cu2 Cl2 167.60(12) . . ? N6 Cu2 Cl2 96.39(11) . . ? N2 Cu2 Cl2 94.86(12) . . ? C23 O1 C6 117.5(4) . . ? C1 N1 C5 117.0(6) . . ? C1 N1 Cu1 122.9(4) . . ? C5 N1 Cu1 119.7(4) . . ? C11 N2 C7 117.9(4) . . ? C11 N2 Cu2 125.8(3) . . ? C7 N2 Cu2 116.2(3) . . ? N4 N3 C6 111.5(3) . . ? N4 N3 Cu2 124.0(3) . . ? C6 N3 Cu2 118.8(3) . . ? C17 N4 N3 123.7(4) . . ? C17 N4 Cu1 113.4(3) . . ? N3 N4 Cu1 122.4(3) . . ? C12 N5 C16 119.1(4) . . ? C12 N5 Cu1 127.3(4) . . ? C16 N5 Cu1 113.5(3) . . ? C18 N6 C22 118.0(4) . . ? C18 N6 Cu2 124.0(3) . . ? C22 N6 Cu2 117.9(3) . . ? N1 C1 C2 124.2(7) . . ? N1 C1 H1A 117.9 . . ? C2 C1 H1A 117.9 . . ? C1 C2 C3 119.3(6) . . ? C1 C2 H2A 120.4 . . ? C3 C2 H2A 120.4 . . ? C2 C3 C4 118.2(7) . . ? C2 C3 H3A 120.9 . . ? C4 C3 H3A 120.9 . . ? C5 C4 C3 119.6(6) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C4 C5 N1 121.7(5) . . ? C4 C5 C6 125.4(5) . . ? N1 C5 C6 112.9(5) . . ? O1 C6 N3 112.9(4) . . ? O1 C6 C5 102.9(4) . . ? N3 C6 C5 109.4(4) . . ? O1 C6 C7 111.2(4) . . ? N3 C6 C7 106.6(4) . . ? C5 C6 C7 114.0(4) . . ? N2 C7 C8 121.5(4) . . ? N2 C7 C6 116.3(4) . . ? C8 C7 C6 121.8(4) . . ? C7 C8 C9 119.1(5) . . ? C7 C8 H8A 120.4 . . ? C9 C8 H8A 120.4 . . ? C10 C9 C8 120.1(5) . . ? C10 C9 H9A 119.9 . . ? C8 C9 H9A 119.9 . . ? C9 C10 C11 118.1(5) . . ? C9 C10 H10A 120.9 . . ? C11 C10 H10A 120.9 . . ? N2 C11 C10 123.1(5) . . ? N2 C11 H11A 118.4 . . ? C10 C11 H11A 118.4 . . ? N5 C12 C13 122.6(5) . . ? N5 C12 H12A 118.7 . . ? C13 C12 H12A 118.7 . . ? C14 C13 C12 118.9(5) . . ? C14 C13 H13A 120.6 . . ? C12 C13 H13A 120.6 . . ? C13 C14 C15 119.2(5) . . ? C13 C14 H14A 120.4 . . ? C15 C14 H14A 120.4 . . ? C14 C15 C16 120.1(5) . . ? C14 C15 H15A 120.0 . . ? C16 C15 H15A 120.0 . . ? N5 C16 C15 120.1(4) . . ? N5 C16 C17 114.5(4) . . ? C15 C16 C17 125.1(4) . . ? N4 C17 C16 113.3(4) . . ? N4 C17 C18 124.7(4) . . ? C16 C17 C18 122.0(4) . . ? N6 C18 C19 121.3(4) . . ? N6 C18 C17 119.9(4) . . ? C19 C18 C17 118.8(4) . . ? C20 C19 C18 119.6(5) . . ? C20 C19 H19A 120.2 . . ? C18 C19 H19A 120.2 . . ? C19 C20 C21 119.1(4) . . ? C19 C20 H20A 120.4 . . ? C21 C20 H20A 120.4 . . ? C22 C21 C20 118.5(5) . . ? C22 C21 H21A 120.8 . . ? C20 C21 H21A 120.8 . . ? N6 C22 C21 123.3(5) . . ? N6 C22 H22A 118.4 . . ? C21 C22 H22A 118.4 . . ? O1 C23 C24 110.8(6) . . ? O1 C23 H23A 109.5 . . ? C24 C23 H23A 109.5 . . ? O1 C23 H23B 109.5 . . ? C24 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C26 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N7 C26 C25 174.7(11) . . ? O12' Cl3 O11 132.5(9) . . ? O12' Cl3 O13 54.6(8) . . ? O11 Cl3 O13 118.3(8) . . ? O12' Cl3 O11' 122.7(9) . . ? O11 Cl3 O11' 42.5(6) . . ? O13 Cl3 O11' 155.9(7) . . ? O12' Cl3 O14 110.4(9) . . ? O11 Cl3 O14 114.0(7) . . ? O13 Cl3 O14 112.7(6) . . ? O11' Cl3 O14 91.0(7) . . ? O12' Cl3 O14' 116.5(9) . . ? O11 Cl3 O14' 110.7(9) . . ? O13 Cl3 O14' 93.9(8) . . ? O11' Cl3 O14' 106.4(7) . . ? O14 Cl3 O14' 27.3(8) . . ? O12' Cl3 O13' 108.8(9) . . ? O11 Cl3 O13' 55.5(7) . . ? O13 Cl3 O13' 65.0(7) . . ? O11' Cl3 O13' 98.0(7) . . ? O14 Cl3 O13' 125.7(7) . . ? O14' Cl3 O13' 100.5(8) . . ? O12' Cl3 O12 49.0(8) . . ? O11 Cl3 O12 106.1(7) . . ? O13 Cl3 O12 103.1(7) . . ? O11' Cl3 O12 75.9(7) . . ? O14 Cl3 O12 99.9(7) . . ? O14' Cl3 O12 124.9(8) . . ? O13' Cl3 O12 134.2(7) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.678 _refine_diff_density_min -0.778 _refine_diff_density_rms 0.091 # Attachment 'compound 4.cif' data_t _database_code_depnum_ccdc_archive 'CCDC 631557' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H19 Cl Cu2 N12 O5' _chemical_formula_weight 706.03 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 25.593(2) _cell_length_b 14.9494(14) _cell_length_c 16.2415(15) _cell_angle_alpha 90.00 _cell_angle_beta 116.503(2) _cell_angle_gamma 90.00 _cell_volume 5561.0(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour 'dark blue' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.687 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2848 _exptl_absorpt_coefficient_mu 1.685 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7021 _exptl_absorpt_correction_T_max 0.5671 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 13899 _diffrn_reflns_av_R_equivalents 0.0773 _diffrn_reflns_av_sigmaI/netI 0.0745 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4903 _reflns_number_gt 3184 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4903 _refine_ls_number_parameters 385 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0738 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1076 _refine_ls_wR_factor_gt 0.1007 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.311137(18) -0.12188(3) -0.00584(3) 0.03733(12) Uani 1 1 d . . . Cu2 Cu 0.394330(18) -0.13167(3) -0.21526(3) 0.03782(12) Uani 1 1 d . . . O1 O 0.30978(10) -0.03210(15) -0.23569(15) 0.0403(6) Uani 1 1 d . . . N2 N 0.42414(11) -0.01403(18) -0.15194(18) 0.0341(7) Uani 1 1 d . . . N1 N 0.27644(12) -0.00030(19) -0.05522(19) 0.0390(8) Uani 1 1 d . . . N3 N 0.34557(11) -0.10282(17) -0.08824(18) 0.0316(7) Uani 1 1 d . . . N4 N 0.36778(11) -0.16404(18) -0.12166(17) 0.0298(7) Uani 1 1 d . . . N5 N 0.36329(12) -0.22858(18) 0.04607(18) 0.0357(7) Uani 1 1 d . . . N6 N 0.40431(12) -0.26116(18) -0.21540(19) 0.0378(7) Uani 1 1 d . . . N7 N 0.25801(14) -0.1373(2) 0.0486(2) 0.0630(10) Uani 1 1 d . . . N8 N 0.25495(13) -0.1894(2) 0.0991(2) 0.0511(9) Uani 1 1 d . . . N9 N 0.24970(15) -0.2422(3) 0.1477(3) 0.0827(13) Uani 1 1 d . . . N10 N 0.39919(17) -0.1080(2) -0.3291(2) 0.0685(10) Uani 1 1 d . . . N11 N 0.39397(13) -0.0336(2) -0.35302(19) 0.0444(8) Uani 1 1 d . . . N12 N 0.39059(15) 0.0399(2) -0.3768(2) 0.0627(11) Uani 1 1 d . . . C11 C 0.47530(15) 0.0198(3) -0.1386(2) 0.0456(10) Uani 1 1 d . . . H11A H 0.4965 -0.0091 -0.1646 0.055 Uiso 1 1 calc R . . C10 C 0.49809(17) 0.0960(3) -0.0878(3) 0.0564(12) Uani 1 1 d . . . H10A H 0.5340 0.1183 -0.0794 0.068 Uiso 1 1 calc R . . C9 C 0.46638(17) 0.1382(3) -0.0499(3) 0.0589(13) Uani 1 1 d . . . H9A H 0.4806 0.1900 -0.0152 0.071 Uiso 1 1 calc R . . C8 C 0.41326(15) 0.1034(2) -0.0636(3) 0.0426(10) Uani 1 1 d . . . H8A H 0.3917 0.1305 -0.0372 0.051 Uiso 1 1 calc R . . C7 C 0.39268(14) 0.0279(2) -0.1168(2) 0.0342(9) Uani 1 1 d . . . C6 C 0.33425(14) -0.0179(2) -0.1394(2) 0.0325(9) Uani 1 1 d . . . C5 C 0.29459(15) 0.0377(2) -0.1126(2) 0.0380(9) Uani 1 1 d . . . C4 C 0.27670(15) 0.1220(2) -0.1483(3) 0.0484(11) Uani 1 1 d . . . H4A H 0.2884 0.1460 -0.1903 0.058 Uiso 1 1 calc R . . C3 C 0.24119(17) 0.1703(3) -0.1211(3) 0.0606(13) Uani 1 1 d . . . H3A H 0.2297 0.2282 -0.1426 0.073 Uiso 1 1 calc R . . C2 C 0.22298(18) 0.1308(3) -0.0608(3) 0.0614(13) Uani 1 1 d . . . H2A H 0.1989 0.1617 -0.0415 0.074 Uiso 1 1 calc R . . C1 C 0.24104(16) 0.0459(3) -0.0303(3) 0.0500(11) Uani 1 1 d . . . H1A H 0.2283 0.0192 0.0093 0.060 Uiso 1 1 calc R . . C12 C 0.37694(16) -0.2515(3) 0.1337(2) 0.0455(10) Uani 1 1 d . . . H12A H 0.3603 -0.2184 0.1645 0.055 Uiso 1 1 calc R . . C13 C 0.41290(17) -0.3189(3) 0.1795(3) 0.0556(12) Uani 1 1 d . . . H13A H 0.4195 -0.3335 0.2390 0.067 Uiso 1 1 calc R . . C14 C 0.43974(18) -0.3657(3) 0.1359(3) 0.0550(12) Uani 1 1 d . . . H14A H 0.4650 -0.4126 0.1658 0.066 Uiso 1 1 calc R . . C15 C 0.42900(16) -0.3427(2) 0.0478(2) 0.0426(10) Uani 1 1 d . . . H15A H 0.4479 -0.3728 0.0187 0.051 Uiso 1 1 calc R . . C16 C 0.38977(14) -0.2743(2) 0.0024(2) 0.0311(9) Uani 1 1 d . . . C17 C 0.38159(14) -0.2453(2) -0.0889(2) 0.0303(8) Uani 1 1 d . . . C18 C 0.39430(14) -0.3048(2) -0.1508(2) 0.0327(9) Uani 1 1 d . . . C19 C 0.39181(17) -0.3975(2) -0.1515(3) 0.0457(10) Uani 1 1 d . . . H19A H 0.3822 -0.4278 -0.1102 0.055 Uiso 1 1 calc R . . C20 C 0.40385(18) -0.4440(3) -0.2142(3) 0.0558(12) Uani 1 1 d . . . H20A H 0.4028 -0.5062 -0.2149 0.067 Uiso 1 1 calc R . . C21 C 0.41731(18) -0.3993(3) -0.2754(3) 0.0575(12) Uani 1 1 d . . . H21A H 0.4266 -0.4305 -0.3166 0.069 Uiso 1 1 calc R . . C22 C 0.41684(16) -0.3073(3) -0.2750(3) 0.0482(10) Uani 1 1 d . . . H22A H 0.4254 -0.2764 -0.3172 0.058 Uiso 1 1 calc R . . C23 C 0.25169(16) -0.0699(3) -0.2773(3) 0.0553(12) Uani 1 1 d . . . H23A H 0.2388 -0.0771 -0.3422 0.083 Uiso 1 1 calc R . . H23B H 0.2254 -0.0307 -0.2672 0.083 Uiso 1 1 calc R . . H23C H 0.2522 -0.1271 -0.2501 0.083 Uiso 1 1 calc R . . Cl1 Cl 0.40762(5) 0.36540(7) -0.02618(7) 0.0586(3) Uani 1 1 d D . . O14 O 0.3939(2) 0.4495(3) 0.0008(4) 0.086(2) Uiso 0.592(3) 1 d PD A 1 O13 O 0.4268(2) 0.3702(4) -0.0955(3) 0.0803(18) Uiso 0.592(3) 1 d PD A 1 O12 O 0.3601(2) 0.3007(4) -0.0453(4) 0.090(2) Uiso 0.592(3) 1 d PD A 1 O11 O 0.4559(2) 0.3263(4) 0.0512(3) 0.0748(17) Uiso 0.592(3) 1 d PD A 1 O24 O 0.3945(3) 0.3530(5) -0.1190(4) 0.075(3) Uiso 0.408(3) 1 d PD A 2 O21 O 0.3925(4) 0.2924(5) 0.0112(6) 0.105(3) Uiso 0.408(3) 1 d PD A 2 O23 O 0.4644(3) 0.3877(8) 0.0279(8) 0.171(5) Uiso 0.408(3) 1 d PD A 2 O22 O 0.3708(3) 0.4384(4) -0.0274(5) 0.0479(19) Uiso 0.408(3) 1 d PD A 2 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 0.0457(2) 0.0349(2) 0.0415(2) 0.00320(19) 0.02864(19) -0.0009(2) Cu2 0.0588(2) 0.0263(2) 0.0406(2) 0.00173(19) 0.0332(2) -0.0013(2) O1 0.0478(13) 0.0382(14) 0.0370(13) 0.0029(11) 0.0209(11) -0.0038(12) N2 0.0382(15) 0.0291(16) 0.0402(16) 0.0017(13) 0.0220(13) -0.0019(13) N1 0.0417(15) 0.0396(18) 0.0425(16) 0.0020(14) 0.0248(14) 0.0046(14) N3 0.0383(14) 0.0262(15) 0.0357(15) 0.0030(12) 0.0213(12) -0.0014(12) N4 0.0352(14) 0.0254(14) 0.0324(15) 0.0000(12) 0.0182(12) -0.0028(12) N5 0.0463(16) 0.0332(16) 0.0303(15) 0.0017(12) 0.0195(13) -0.0099(13) N6 0.0513(16) 0.0282(16) 0.0405(16) -0.0009(13) 0.0264(14) -0.0003(14) N7 0.0795(19) 0.056(2) 0.086(2) 0.0192(18) 0.0661(17) 0.0072(18) N8 0.0484(17) 0.063(2) 0.0491(19) -0.0118(17) 0.0287(15) -0.0204(17) N9 0.071(2) 0.114(3) 0.067(2) 0.022(2) 0.034(2) -0.028(2) N10 0.136(3) 0.037(2) 0.0646(19) 0.0044(15) 0.074(2) 0.011(2) N11 0.0514(17) 0.052(2) 0.0376(17) 0.0083(15) 0.0272(14) 0.0023(16) N12 0.069(2) 0.056(2) 0.062(2) 0.0242(18) 0.0271(19) 0.0003(19) C11 0.0445(19) 0.043(2) 0.060(2) 0.0011(18) 0.0325(18) -0.0027(18) C10 0.056(2) 0.040(2) 0.082(3) -0.007(2) 0.038(2) -0.0130(19) C9 0.058(2) 0.036(2) 0.077(3) -0.019(2) 0.025(2) -0.010(2) C8 0.049(2) 0.028(2) 0.057(2) -0.0074(17) 0.0283(18) -0.0016(17) C7 0.0460(19) 0.0223(18) 0.0400(19) 0.0083(15) 0.0241(16) 0.0050(16) C6 0.0402(18) 0.0240(18) 0.0371(19) 0.0055(14) 0.0207(16) 0.0036(15) C5 0.0400(18) 0.034(2) 0.044(2) -0.0002(16) 0.0218(17) -0.0026(16) C4 0.051(2) 0.035(2) 0.065(2) 0.0062(19) 0.0314(19) 0.0060(18) C3 0.062(2) 0.045(2) 0.079(3) 0.006(2) 0.035(2) 0.017(2) C2 0.060(2) 0.056(3) 0.077(3) -0.009(2) 0.038(2) 0.013(2) C1 0.057(2) 0.053(3) 0.054(2) 0.0036(19) 0.0369(19) 0.009(2) C12 0.055(2) 0.049(2) 0.040(2) 0.0037(18) 0.0283(18) -0.001(2) C13 0.071(3) 0.059(3) 0.038(2) 0.016(2) 0.024(2) 0.000(2) C14 0.072(3) 0.043(2) 0.044(2) 0.0087(19) 0.021(2) 0.007(2) C15 0.055(2) 0.034(2) 0.038(2) 0.0039(16) 0.0194(18) 0.0017(18) C16 0.0385(18) 0.0265(18) 0.0283(18) -0.0029(14) 0.0148(15) -0.0109(15) C17 0.0365(17) 0.0243(18) 0.0314(18) -0.0020(14) 0.0163(15) -0.0076(15) C18 0.0377(18) 0.0269(18) 0.0335(19) -0.0008(15) 0.0160(16) -0.0012(16) C19 0.068(2) 0.026(2) 0.044(2) 0.0034(16) 0.0259(19) -0.0015(18) C20 0.085(3) 0.026(2) 0.056(2) -0.0056(18) 0.031(2) 0.005(2) C21 0.086(3) 0.042(2) 0.053(2) -0.0072(19) 0.039(2) 0.013(2) C22 0.070(2) 0.040(2) 0.047(2) -0.0007(17) 0.0371(19) 0.007(2) C23 0.047(2) 0.065(3) 0.047(2) -0.001(2) 0.015(2) -0.002(2) Cl1 0.0829(6) 0.0489(6) 0.0599(6) 0.0075(5) 0.0462(5) 0.0110(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 1.924(3) . ? Cu1 N7 1.938(3) . ? Cu1 N5 2.008(3) . ? Cu1 N1 2.025(3) . ? Cu2 N10 1.940(3) . ? Cu2 N6 1.953(3) . ? Cu2 N4 1.982(3) . ? Cu2 N2 2.008(3) . ? O1 C6 1.417(4) . ? O1 C23 1.446(4) . ? N2 C11 1.328(4) . ? N2 C7 1.333(4) . ? N1 C1 1.338(5) . ? N1 C5 1.339(4) . ? N3 N4 1.316(4) . ? N3 C6 1.474(4) . ? N4 C17 1.310(4) . ? N5 C12 1.350(4) . ? N5 C16 1.364(4) . ? N6 C22 1.339(5) . ? N6 C18 1.353(4) . ? N7 N8 1.158(4) . ? N8 N9 1.166(5) . ? N10 N11 1.166(4) . ? N11 N12 1.155(4) . ? C11 C10 1.374(5) . ? C11 H11A 0.9300 . ? C10 C9 1.372(6) . ? C10 H10A 0.9300 . ? C9 C8 1.378(5) . ? C9 H9A 0.9300 . ? C8 C7 1.375(5) . ? C8 H8A 0.9300 . ? C7 C6 1.533(5) . ? C6 C5 1.518(5) . ? C5 C4 1.377(5) . ? C4 C3 1.380(6) . ? C4 H4A 0.9300 . ? C3 C2 1.390(6) . ? C3 H3A 0.9300 . ? C2 C1 1.366(5) . ? C2 H2A 0.9300 . ? C1 H1A 0.9300 . ? C12 C13 1.343(5) . ? C12 H12A 0.9300 . ? C13 C14 1.378(6) . ? C13 H13A 0.9300 . ? C14 C15 1.373(5) . ? C14 H14A 0.9300 . ? C15 C16 1.392(5) . ? C15 H15A 0.9300 . ? C16 C17 1.467(4) . ? C17 C18 1.484(5) . ? C18 C19 1.387(5) . ? C19 C20 1.377(5) . ? C19 H19A 0.9300 . ? C20 C21 1.362(6) . ? C20 H20A 0.9300 . ? C21 C22 1.376(5) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? Cl1 O23 1.362(7) . ? Cl1 O21 1.385(6) . ? Cl1 O24 1.403(6) . ? Cl1 O13 1.417(5) . ? Cl1 O14 1.425(5) . ? Cl1 O22 1.435(5) . ? Cl1 O11 1.436(4) . ? Cl1 O12 1.475(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cu1 N7 165.29(12) . . ? N3 Cu1 N5 89.13(11) . . ? N7 Cu1 N5 100.61(13) . . ? N3 Cu1 N1 81.22(12) . . ? N7 Cu1 N1 90.84(13) . . ? N5 Cu1 N1 166.21(11) . . ? N10 Cu2 N6 96.62(13) . . ? N10 Cu2 N4 164.81(13) . . ? N6 Cu2 N4 81.29(12) . . ? N10 Cu2 N2 99.06(13) . . ? N6 Cu2 N2 148.08(11) . . ? N4 Cu2 N2 90.17(11) . . ? C6 O1 C23 115.5(3) . . ? C11 N2 C7 119.4(3) . . ? C11 N2 Cu2 122.6(3) . . ? C7 N2 Cu2 117.8(2) . . ? C1 N1 C5 119.0(3) . . ? C1 N1 Cu1 125.4(3) . . ? C5 N1 Cu1 115.4(2) . . ? N4 N3 C6 112.3(3) . . ? N4 N3 Cu1 126.9(2) . . ? C6 N3 Cu1 119.0(2) . . ? C17 N4 N3 124.4(3) . . ? C17 N4 Cu2 114.5(2) . . ? N3 N4 Cu2 120.4(2) . . ? C12 N5 C16 117.8(3) . . ? C12 N5 Cu1 117.1(3) . . ? C16 N5 Cu1 124.8(2) . . ? C22 N6 C18 120.1(3) . . ? C22 N6 Cu2 125.8(3) . . ? C18 N6 Cu2 114.0(2) . . ? N8 N7 Cu1 133.3(3) . . ? N7 N8 N9 177.5(4) . . ? N11 N10 Cu2 116.4(3) . . ? N12 N11 N10 177.7(4) . . ? N2 C11 C10 122.5(4) . . ? N2 C11 H11A 118.7 . . ? C10 C11 H11A 118.7 . . ? C9 C10 C11 118.2(4) . . ? C9 C10 H10A 120.9 . . ? C11 C10 H10A 120.9 . . ? C10 C9 C8 119.5(4) . . ? C10 C9 H9A 120.3 . . ? C8 C9 H9A 120.3 . . ? C7 C8 C9 119.0(4) . . ? C7 C8 H8A 120.5 . . ? C9 C8 H8A 120.5 . . ? N2 C7 C8 121.3(3) . . ? N2 C7 C6 113.5(3) . . ? C8 C7 C6 125.2(3) . . ? O1 C6 N3 111.8(3) . . ? O1 C6 C5 112.1(3) . . ? N3 C6 C5 107.3(3) . . ? O1 C6 C7 103.6(3) . . ? N3 C6 C7 108.9(2) . . ? C5 C6 C7 113.1(3) . . ? N1 C5 C4 121.9(4) . . ? N1 C5 C6 116.8(3) . . ? C4 C5 C6 121.3(3) . . ? C5 C4 C3 119.1(4) . . ? C5 C4 H4A 120.4 . . ? C3 C4 H4A 120.4 . . ? C4 C3 C2 118.7(4) . . ? C4 C3 H3A 120.7 . . ? C2 C3 H3A 120.7 . . ? C1 C2 C3 119.0(4) . . ? C1 C2 H2A 120.5 . . ? C3 C2 H2A 120.5 . . ? N1 C1 C2 122.3(4) . . ? N1 C1 H1A 118.8 . . ? C2 C1 H1A 118.8 . . ? C13 C12 N5 124.4(4) . . ? C13 C12 H12A 117.8 . . ? N5 C12 H12A 117.8 . . ? C12 C13 C14 118.2(4) . . ? C12 C13 H13A 120.9 . . ? C14 C13 H13A 120.9 . . ? C15 C14 C13 119.6(4) . . ? C15 C14 H14A 120.2 . . ? C13 C14 H14A 120.2 . . ? C14 C15 C16 119.9(4) . . ? C14 C15 H15A 120.1 . . ? C16 C15 H15A 120.1 . . ? N5 C16 C15 120.0(3) . . ? N5 C16 C17 119.8(3) . . ? C15 C16 C17 119.8(3) . . ? N4 C17 C16 125.2(3) . . ? N4 C17 C18 112.4(3) . . ? C16 C17 C18 122.1(3) . . ? N6 C18 C19 120.0(3) . . ? N6 C18 C17 114.3(3) . . ? C19 C18 C17 125.5(3) . . ? C20 C19 C18 119.0(4) . . ? C20 C19 H19A 120.5 . . ? C18 C19 H19A 120.5 . . ? C21 C20 C19 120.3(4) . . ? C21 C20 H20A 119.8 . . ? C19 C20 H20A 119.8 . . ? C20 C21 C22 118.8(4) . . ? C20 C21 H21A 120.6 . . ? C22 C21 H21A 120.6 . . ? N6 C22 C21 121.6(4) . . ? N6 C22 H22A 119.2 . . ? C21 C22 H22A 119.2 . . ? O1 C23 H23A 109.5 . . ? O1 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O1 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O23 Cl1 O21 109.6(6) . . ? O23 Cl1 O24 113.5(6) . . ? O21 Cl1 O24 112.8(5) . . ? O23 Cl1 O13 81.4(6) . . ? O21 Cl1 O13 130.6(4) . . ? O24 Cl1 O13 32.3(3) . . ? O23 Cl1 O14 85.7(6) . . ? O21 Cl1 O14 113.9(5) . . ? O24 Cl1 O14 118.2(4) . . ? O13 Cl1 O14 114.8(3) . . ? O23 Cl1 O22 109.1(6) . . ? O21 Cl1 O22 107.2(5) . . ? O24 Cl1 O22 104.2(4) . . ? O13 Cl1 O22 114.1(4) . . ? O14 Cl1 O22 23.7(3) . . ? O23 Cl1 O11 44.0(5) . . ? O21 Cl1 O11 66.1(4) . . ? O24 Cl1 O11 125.9(4) . . ? O13 Cl1 O11 104.3(3) . . ? O14 Cl1 O11 108.9(3) . . ? O22 Cl1 O11 128.6(4) . . ? O23 Cl1 O12 147.0(6) . . ? O21 Cl1 O12 37.9(4) . . ? O24 Cl1 O12 84.7(4) . . ? O13 Cl1 O12 114.3(3) . . ? O14 Cl1 O12 110.5(3) . . ? O22 Cl1 O12 91.2(3) . . ? O11 Cl1 O12 103.0(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 N10 Cu2 N2 C11 -55.1(3) . . . . ? N6 Cu2 N2 C11 63.4(4) . . . . ? N4 Cu2 N2 C11 137.1(3) . . . . ? N10 Cu2 N2 C7 129.6(2) . . . . ? N6 Cu2 N2 C7 -111.9(3) . . . . ? N4 Cu2 N2 C7 -38.3(2) . . . . ? N3 Cu1 N1 C1 -179.2(3) . . . . ? N7 Cu1 N1 C1 13.2(3) . . . . ? N5 Cu1 N1 C1 -133.2(5) . . . . ? N3 Cu1 N1 C5 -4.1(2) . . . . ? N7 Cu1 N1 C5 -171.7(2) . . . . ? N5 Cu1 N1 C5 42.0(6) . . . . ? N7 Cu1 N3 N4 -102.8(5) . . . . ? N5 Cu1 N3 N4 29.1(2) . . . . ? N1 Cu1 N3 N4 -160.8(3) . . . . ? N7 Cu1 N3 C6 60.4(6) . . . . ? N5 Cu1 N3 C6 -167.8(2) . . . . ? N1 Cu1 N3 C6 2.3(2) . . . . ? C6 N3 N4 C17 -179.7(3) . . . . ? Cu1 N3 N4 C17 -15.7(4) . . . . ? C6 N3 N4 Cu2 10.0(3) . . . . ? Cu1 N3 N4 Cu2 174.09(12) . . . . ? N10 Cu2 N4 C17 98.4(5) . . . . ? N6 Cu2 N4 C17 15.2(2) . . . . ? N2 Cu2 N4 C17 -133.9(2) . . . . ? N10 Cu2 N4 N3 -90.4(5) . . . . ? N6 Cu2 N4 N3 -173.6(2) . . . . ? N2 Cu2 N4 N3 37.3(2) . . . . ? N3 Cu1 N5 C12 153.2(3) . . . . ? N7 Cu1 N5 C12 -37.9(3) . . . . ? N1 Cu1 N5 C12 107.8(5) . . . . ? N3 Cu1 N5 C16 -20.8(3) . . . . ? N7 Cu1 N5 C16 148.1(3) . . . . ? N1 Cu1 N5 C16 -66.2(6) . . . . ? N10 Cu2 N6 C22 6.3(3) . . . . ? N4 Cu2 N6 C22 171.1(3) . . . . ? N2 Cu2 N6 C22 -112.8(3) . . . . ? N10 Cu2 N6 C18 -170.3(2) . . . . ? N4 Cu2 N6 C18 -5.5(2) . . . . ? N2 Cu2 N6 C18 70.7(3) . . . . ? N3 Cu1 N7 N8 132.8(5) . . . . ? N5 Cu1 N7 N8 2.0(4) . . . . ? N1 Cu1 N7 N8 -170.3(4) . . . . ? Cu1 N7 N8 N9 -130(11) . . . . ? N6 Cu2 N10 N11 178.9(3) . . . . ? N4 Cu2 N10 N11 97.8(5) . . . . ? N2 Cu2 N10 N11 -29.0(3) . . . . ? Cu2 N10 N11 N12 125(10) . . . . ? C7 N2 C11 C10 1.5(5) . . . . ? Cu2 N2 C11 C10 -173.8(3) . . . . ? N2 C11 C10 C9 -0.1(6) . . . . ? C11 C10 C9 C8 0.1(6) . . . . ? C10 C9 C8 C7 -1.4(6) . . . . ? C11 N2 C7 C8 -2.9(5) . . . . ? Cu2 N2 C7 C8 172.6(3) . . . . ? C11 N2 C7 C6 178.8(3) . . . . ? Cu2 N2 C7 C6 -5.7(4) . . . . ? C9 C8 C7 N2 2.9(5) . . . . ? C9 C8 C7 C6 -179.1(3) . . . . ? C23 O1 C6 N3 66.7(4) . . . . ? C23 O1 C6 C5 -53.9(4) . . . . ? C23 O1 C6 C7 -176.1(3) . . . . ? N4 N3 C6 O1 41.8(3) . . . . ? Cu1 N3 C6 O1 -123.7(2) . . . . ? N4 N3 C6 C5 165.0(2) . . . . ? Cu1 N3 C6 C5 -0.4(3) . . . . ? N4 N3 C6 C7 -72.1(3) . . . . ? Cu1 N3 C6 C7 122.4(2) . . . . ? N2 C7 C6 O1 -49.2(3) . . . . ? C8 C7 C6 O1 132.6(3) . . . . ? N2 C7 C6 N3 70.0(3) . . . . ? C8 C7 C6 N3 -108.2(4) . . . . ? N2 C7 C6 C5 -170.8(3) . . . . ? C8 C7 C6 C5 11.1(5) . . . . ? C1 N1 C5 C4 -1.6(5) . . . . ? Cu1 N1 C5 C4 -177.1(3) . . . . ? C1 N1 C5 C6 -179.5(3) . . . . ? Cu1 N1 C5 C6 5.1(4) . . . . ? O1 C6 C5 N1 120.1(3) . . . . ? N3 C6 C5 N1 -3.0(4) . . . . ? C7 C6 C5 N1 -123.2(3) . . . . ? O1 C6 C5 C4 -57.8(4) . . . . ? N3 C6 C5 C4 179.1(3) . . . . ? C7 C6 C5 C4 58.9(4) . . . . ? N1 C5 C4 C3 3.0(5) . . . . ? C6 C5 C4 C3 -179.3(3) . . . . ? C5 C4 C3 C2 -2.3(6) . . . . ? C4 C3 C2 C1 0.3(6) . . . . ? C5 N1 C1 C2 -0.4(5) . . . . ? Cu1 N1 C1 C2 174.5(3) . . . . ? C3 C2 C1 N1 1.1(6) . . . . ? C16 N5 C12 C13 -3.0(5) . . . . ? Cu1 N5 C12 C13 -177.5(3) . . . . ? N5 C12 C13 C14 2.8(6) . . . . ? C12 C13 C14 C15 -0.2(6) . . . . ? C13 C14 C15 C16 -2.0(6) . . . . ? C12 N5 C16 C15 0.6(5) . . . . ? Cu1 N5 C16 C15 174.6(2) . . . . ? C12 N5 C16 C17 -173.0(3) . . . . ? Cu1 N5 C16 C17 1.0(4) . . . . ? C14 C15 C16 N5 1.8(5) . . . . ? C14 C15 C16 C17 175.4(3) . . . . ? N3 N4 C17 C16 -17.4(5) . . . . ? Cu2 N4 C17 C16 153.4(3) . . . . ? N3 N4 C17 C18 168.4(3) . . . . ? Cu2 N4 C17 C18 -20.8(3) . . . . ? N5 C16 C17 N4 24.2(5) . . . . ? C15 C16 C17 N4 -149.4(3) . . . . ? N5 C16 C17 C18 -162.1(3) . . . . ? C15 C16 C17 C18 24.2(5) . . . . ? C22 N6 C18 C19 -5.8(5) . . . . ? Cu2 N6 C18 C19 171.0(3) . . . . ? C22 N6 C18 C17 179.4(3) . . . . ? Cu2 N6 C18 C17 -3.8(3) . . . . ? N4 C17 C18 N6 16.3(4) . . . . ? C16 C17 C18 N6 -158.1(3) . . . . ? N4 C17 C18 C19 -158.2(3) . . . . ? C16 C17 C18 C19 27.4(5) . . . . ? N6 C18 C19 C20 4.7(5) . . . . ? C17 C18 C19 C20 178.9(3) . . . . ? C18 C19 C20 C21 -0.8(6) . . . . ? C19 C20 C21 C22 -2.0(6) . . . . ? C18 N6 C22 C21 3.0(5) . . . . ? Cu2 N6 C22 C21 -173.4(3) . . . . ? C20 C21 C22 N6 0.9(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.903 _refine_diff_density_min -0.487 _refine_diff_density_rms 0.081