Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Shie-Ming Peng' _publ_contact_author_address ; Department of Chemistry National Taiwan Univeristy Taipei TAIWAN ; _publ_contact_author_email SMPENG@MAIL.CH.NTU.EDU.TW _publ_section_title ; One, two and three-dimensional Cu(II) complexes built via new oligopyrazinediamine ligands: from antiferromagnetic to ferro- magnetic coupling ; loop_ _publ_author_name 'Shie-Ming Peng' 'Rayyat H. Ismayilov' 'Gene-Hsiang Lee' 'Wen-Zhen Wang' data_ic10693 _database_code_depnum_ccdc_archive 'CCDC 273183' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H21 Cl2 Cu N6 O10' _chemical_formula_weight 603.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Pcca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x, y, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x, -y, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 20.9474(4) _cell_length_b 8.1081(2) _cell_length_c 13.7728(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2339.22(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used all _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour dark-green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.715 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 1.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.644 _exptl_absorpt_correction_T_max 0.776 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'NONIUS KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15499 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2691 _reflns_number_gt 1951 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0822P)^2^+2.1987P] 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 2691 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0739 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1438 _refine_ls_wR_factor_gt 0.1290 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 Cu Cu 0.2500 1.0000 0.58126(3) 0.02163(19) Uani 1 2 d S . . O1 O 0.32100(11) 0.7713(3) 0.58535(15) 0.0385(6) Uani 1 1 d . . . H1A H 0.3011 0.6903 0.5536 0.058 Uiso 1 1 d . . . N1 N 0.17834(11) 0.8363(3) 0.57799(15) 0.0242(5) Uani 1 1 d . . . N2 N 0.13951(12) 0.9468(4) 0.43074(17) 0.0286(6) Uani 1 1 d . . . H2A H 0.1053 0.9933 0.4058 0.034 Uiso 1 1 calc R . . N3 N 0.2500 1.0000 0.4350(2) 0.0228(7) Uani 1 2 d S . . N4 N 0.2500 1.0000 0.2328(2) 0.0216(7) Uani 1 2 d S . . C1 C 0.16975(15) 0.7246(4) 0.65024(19) 0.0297(7) Uani 1 1 d . . . H1B H 0.2043 0.7036 0.6931 0.036 Uiso 1 1 calc R . . C2 C 0.11405(17) 0.6409(5) 0.6644(2) 0.0379(8) Uani 1 1 d . . . H2B H 0.1106 0.5625 0.7154 0.045 Uiso 1 1 calc R . . C3 C 0.06199(17) 0.6714(5) 0.6035(2) 0.0413(9) Uani 1 1 d . . . C4 C 0.07170(15) 0.7757(4) 0.5262(2) 0.0356(8) Uani 1 1 d . . . H4A H 0.0382 0.7956 0.4813 0.043 Uiso 1 1 calc R . . C5 C 0.13059(14) 0.8523(4) 0.51383(19) 0.0255(6) Uani 1 1 d . . . C6 C 0.19618(14) 0.9752(4) 0.3837(2) 0.0240(6) Uani 1 1 d . . . C7 C 0.19629(15) 0.9756(4) 0.2825(2) 0.0253(6) Uani 1 1 d . . . H7A H 0.1574 0.9582 0.2485 0.030 Uiso 1 1 calc R . . C8 C -0.0022(2) 0.5941(7) 0.6212(3) 0.0673(14) Uani 1 1 d . . . H8A H -0.0245 0.5796 0.5592 0.101 Uiso 1 1 calc R . . H8B H -0.0275 0.6658 0.6636 0.101 Uiso 1 1 calc R . . H8C H 0.0035 0.4865 0.6524 0.101 Uiso 1 1 calc R . . C9 C 0.3801(5) 0.7460(14) 0.5659(10) 0.101(4) Uani 0.50 1 d P . . H9A H 0.3923 0.6354 0.5878 0.151 Uiso 0.50 1 calc PR . . H9B H 0.4063 0.8284 0.5995 0.151 Uiso 0.50 1 calc PR . . H9C H 0.3869 0.7550 0.4957 0.151 Uiso 0.50 1 calc PR . . Cl1 Cl 0.5000 0.8992(2) 0.7500 0.0814(6) Uani 1 2 d S . . O2 O 0.5176(5) 0.979(2) 0.6747(8) 0.092(4) Uani 0.50 1 d P . . O3 O 0.4599(5) 1.0223(19) 0.8005(12) 0.102(4) Uani 0.50 1 d P . . O4 O 0.4558(4) 0.7786(10) 0.7668(7) 0.097(3) Uani 0.50 1 d P . . O5 O 0.5522(3) 0.8494(16) 0.8316(10) 0.151(6) Uani 0.50 1 d P . . Cl2 Cl 0.2500 0.5000 0.39161(10) 0.0506(4) Uani 1 2 d S . . O6 O 0.2500 0.5000 0.4952(3) 0.0746(16) Uani 1 2 d S . . O7 O 0.3062(8) 0.419(2) 0.3520(12) 0.188(9) Uani 0.50 1 d P . . O8 O 0.2352(5) 0.6371(9) 0.3494(5) 0.066(2) Uani 0.50 1 d P . . O9 O 0.2010(6) 0.3680(11) 0.3773(8) 0.128(4) Uani 0.50 1 d P . . 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 Cu 0.0282(3) 0.0278(3) 0.0089(3) 0.000 0.000 -0.0027(2) O1 0.0409(13) 0.0359(13) 0.0385(13) -0.0067(10) -0.0004(10) 0.0035(11) N1 0.0297(13) 0.0299(13) 0.0130(11) 0.0000(9) 0.0029(9) -0.0048(11) N2 0.0256(13) 0.0446(15) 0.0156(11) 0.0068(10) 0.0000(10) -0.0042(11) N3 0.0281(18) 0.0283(19) 0.0120(14) 0.000 0.000 -0.0024(14) N4 0.0275(17) 0.0258(17) 0.0115(14) 0.000 0.000 -0.0025(14) C1 0.0419(18) 0.0328(17) 0.0144(12) 0.0011(12) 0.0002(12) 0.0007(14) C2 0.052(2) 0.042(2) 0.0191(14) 0.0089(13) 0.0024(14) -0.0132(17) C3 0.049(2) 0.051(2) 0.0238(15) 0.0006(15) 0.0032(14) -0.0203(17) C4 0.0377(18) 0.050(2) 0.0186(14) 0.0013(14) -0.0010(12) -0.0122(15) C5 0.0325(15) 0.0303(16) 0.0136(12) -0.0008(11) 0.0035(11) -0.0035(13) C6 0.0279(15) 0.0303(16) 0.0137(13) 0.0001(11) -0.0018(11) -0.0019(12) C7 0.0278(15) 0.0331(17) 0.0149(13) 0.0023(11) -0.0002(11) -0.0023(12) C8 0.059(3) 0.102(4) 0.041(2) 0.023(2) -0.0046(19) -0.044(3) C9 0.085(8) 0.064(7) 0.153(12) 0.013(7) -0.034(8) 0.009(6) Cl1 0.0912(14) 0.0563(10) 0.0967(15) 0.000 0.0532(11) 0.000 O2 0.040(6) 0.175(14) 0.060(6) 0.028(7) 0.007(4) -0.006(6) O3 0.047(7) 0.133(9) 0.124(11) 0.014(7) 0.045(7) 0.030(6) O4 0.083(5) 0.075(5) 0.133(8) -0.018(5) 0.028(5) -0.005(4) O5 0.042(4) 0.189(11) 0.222(13) 0.159(11) -0.019(6) 0.014(5) Cl2 0.0875(11) 0.0410(7) 0.0233(6) 0.000 0.000 0.0021(7) O6 0.145(5) 0.047(3) 0.032(2) 0.000 0.000 -0.010(2) O7 0.209(16) 0.142(13) 0.213(16) 0.068(11) 0.155(14) 0.100(12) O8 0.116(7) 0.037(4) 0.044(4) 0.026(3) 0.021(4) 0.019(4) O9 0.193(11) 0.082(6) 0.111(7) 0.032(5) -0.086(8) -0.067(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N1 2.004(2) . ? Cu N1 2.004(2) 2_575 ? Cu N3 2.015(3) . ? Cu N4 2.086(3) 7_576 ? Cu O1 2.378(2) 2_575 ? Cu O1 2.378(2) . ? O1 C9 1.284(11) . ? N1 C5 1.341(4) . ? N1 C1 1.358(4) . ? N2 C6 1.372(4) . ? N2 C5 1.390(4) . ? N3 C6 1.346(3) . ? N3 C6 1.346(3) 2_575 ? N4 C7 1.332(3) . ? N4 C7 1.332(3) 2_575 ? N4 Cu 2.086(3) 7_575 ? C1 C2 1.363(5) . ? C2 C3 1.398(5) . ? C3 C4 1.374(5) . ? C3 C8 1.504(5) . ? C4 C5 1.392(4) . ? C6 C7 1.393(4) . ? Cl1 O2 1.275(12) 3_656 ? Cl1 O2 1.275(12) . ? Cl1 O4 1.367(8) . ? Cl1 O4 1.367(8) 3_656 ? Cl1 O3 1.478(13) . ? Cl1 O3 1.478(13) 3_656 ? Cl1 O5 1.620(8) 3_656 ? Cl1 O5 1.620(8) . ? O2 O3 0.682(14) 3_656 ? O2 O5 1.801(14) 3_656 ? O3 O2 0.682(14) 3_656 ? O4 O5 1.481(15) 3_656 ? O5 O4 1.481(15) 3_656 ? O5 O2 1.801(14) 3_656 ? Cl2 O8 1.293(6) 2_565 ? Cl2 O8 1.293(6) . ? Cl2 O6 1.427(4) . ? Cl2 O7 1.455(11) 2_565 ? Cl2 O7 1.455(11) . ? Cl2 O9 1.495(8) . ? Cl2 O9 1.495(8) 2_565 ? O7 O8 0.979(17) 2_565 ? O7 O9 1.770(18) 2_565 ? O8 O7 0.979(17) 2_565 ? O8 O9 1.392(13) 2_565 ? O9 O8 1.392(13) 2_565 ? O9 O7 1.770(18) 2_565 ? 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 Cu N1 177.42(12) . 2_575 ? N1 Cu N3 88.71(6) . . ? N1 Cu N3 88.71(6) 2_575 . ? N1 Cu N4 91.29(6) . 7_576 ? N1 Cu N4 91.29(6) 2_575 7_576 ? N3 Cu N4 180.000(1) . 7_576 ? N1 Cu O1 92.79(10) . 2_575 ? N1 Cu O1 87.28(10) 2_575 2_575 ? N3 Cu O1 91.36(5) . 2_575 ? N4 Cu O1 88.64(5) 7_576 2_575 ? N1 Cu O1 87.28(10) . . ? N1 Cu O1 92.79(10) 2_575 . ? N3 Cu O1 91.36(5) . . ? N4 Cu O1 88.64(5) 7_576 . ? O1 Cu O1 177.29(10) 2_575 . ? C9 O1 Cu 136.3(6) . . ? C5 N1 C1 116.7(2) . . ? C5 N1 Cu 120.62(19) . . ? C1 N1 Cu 121.65(19) . . ? C6 N2 C5 126.7(3) . . ? C6 N3 C6 116.7(3) . 2_575 ? C6 N3 Cu 121.67(17) . . ? C6 N3 Cu 121.67(17) 2_575 . ? C7 N4 C7 118.1(3) . 2_575 ? C7 N4 Cu 120.96(17) . 7_575 ? C7 N4 Cu 120.96(17) 2_575 7_575 ? N1 C1 C2 123.4(3) . . ? C1 C2 C3 119.6(3) . . ? C4 C3 C2 117.3(3) . . ? C4 C3 C8 121.0(3) . . ? C2 C3 C8 121.8(3) . . ? C3 C4 C5 120.1(3) . . ? N1 C5 N2 119.7(2) . . ? N1 C5 C4 122.5(3) . . ? N2 C5 C4 117.8(3) . . ? N3 C6 N2 120.1(3) . . ? N3 C6 C7 121.6(3) . . ? N2 C6 C7 118.3(3) . . ? N4 C7 C6 121.1(3) . . ? O2 Cl1 O2 119.4(15) 3_656 . ? O2 Cl1 O4 91.6(8) 3_656 . ? O2 Cl1 O4 134.0(7) . . ? O2 Cl1 O4 134.0(7) 3_656 3_656 ? O2 Cl1 O4 91.6(8) . 3_656 ? O4 Cl1 O4 88.7(7) . 3_656 ? O2 Cl1 O3 27.4(7) 3_656 . ? O2 Cl1 O3 101.9(6) . . ? O4 Cl1 O3 91.1(7) . . ? O4 Cl1 O3 161.4(7) 3_656 . ? O2 Cl1 O3 101.9(6) 3_656 3_656 ? O2 Cl1 O3 27.4(7) . 3_656 ? O4 Cl1 O3 161.4(8) . 3_656 ? O4 Cl1 O3 91.1(7) 3_656 3_656 ? O3 Cl1 O3 95.1(12) . 3_656 ? O2 Cl1 O5 119.7(5) 3_656 3_656 ? O2 Cl1 O5 75.9(7) . 3_656 ? O4 Cl1 O5 58.7(6) . 3_656 ? O4 Cl1 O5 99.3(6) 3_656 3_656 ? O3 Cl1 O5 96.4(7) . 3_656 ? O3 Cl1 O5 103.0(8) 3_656 3_656 ? O2 Cl1 O5 75.9(7) 3_656 . ? O2 Cl1 O5 119.7(5) . . ? O4 Cl1 O5 99.3(6) . . ? O4 Cl1 O5 58.7(5) 3_656 . ? O3 Cl1 O5 103.0(8) . . ? O3 Cl1 O5 96.4(7) 3_656 . ? O5 Cl1 O5 151.1(10) 3_656 . ? O3 O2 Cl1 93(2) 3_656 . ? O3 O2 O5 153(2) 3_656 3_656 ? Cl1 O2 O5 60.7(7) . 3_656 ? O2 O3 Cl1 59.5(18) 3_656 . ? Cl1 O4 O5 69.2(5) . 3_656 ? O4 O5 Cl1 52.1(4) 3_656 . ? O4 O5 O2 95.2(6) 3_656 3_656 ? Cl1 O5 O2 43.4(4) . 3_656 ? O8 Cl2 O8 126.5(7) 2_565 . ? O8 Cl2 O6 116.7(3) 2_565 . ? O8 Cl2 O6 116.7(3) . . ? O8 Cl2 O7 114.5(5) 2_565 2_565 ? O8 Cl2 O7 41.2(7) . 2_565 ? O6 Cl2 O7 112.0(7) . 2_565 ? O8 Cl2 O7 41.2(7) 2_565 . ? O8 Cl2 O7 114.5(5) . . ? O6 Cl2 O7 112.0(7) . . ? O7 Cl2 O7 136.0(14) 2_565 . ? O8 Cl2 O9 59.4(5) 2_565 . ? O8 Cl2 O9 113.0(5) . . ? O6 Cl2 O9 97.6(4) . . ? O7 Cl2 O9 73.7(7) 2_565 . ? O7 Cl2 O9 100.5(9) . . ? O8 Cl2 O9 113.0(5) 2_565 2_565 ? O8 Cl2 O9 59.4(5) . 2_565 ? O6 Cl2 O9 97.6(4) . 2_565 ? O7 Cl2 O9 100.5(9) 2_565 2_565 ? O7 Cl2 O9 73.7(7) . 2_565 ? O9 Cl2 O9 164.9(8) . 2_565 ? O8 O7 Cl2 60.4(7) 2_565 . ? O8 O7 O9 112.6(12) 2_565 2_565 ? Cl2 O7 O9 54.2(5) . 2_565 ? O7 O8 Cl2 78.3(9) 2_565 . ? O7 O8 O9 145.7(12) 2_565 2_565 ? Cl2 O8 O9 67.6(5) . 2_565 ? O8 O9 Cl2 53.0(4) 2_565 . ? O8 O9 O7 93.3(8) 2_565 2_565 ? Cl2 O9 O7 52.1(5) . 2_565 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.664 _refine_diff_density_min -0.630 _refine_diff_density_rms 0.091 data_ic10121 _database_code_depnum_ccdc_archive 'CCDC 273184' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 Cl2 Cu N8 O12' _chemical_formula_weight 600.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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' _cell_length_a 13.7508(3) _cell_length_b 8.0150(2) _cell_length_c 19.3724(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2135.08(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used all _cell_measurement_theta_min 2.10 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour pale-green _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 1.869 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1220 _exptl_absorpt_coefficient_mu 1.355 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.749 _exptl_absorpt_correction_T_max 0.824 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'NONIUS KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14029 _diffrn_reflns_av_R_equivalents 0.0411 _diffrn_reflns_av_sigmaI/netI 0.0477 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4458 _reflns_number_gt 3559 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0930P)^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 SHELXL _refine_ls_extinction_coef 0.0179(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.019(18) _refine_ls_number_reflns 4458 _refine_ls_number_parameters 317 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0741 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1458 _refine_ls_wR_factor_gt 0.1211 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.006 _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 0.28140(3) 1.24708(8) 0.09998(4) 0.02069(19) Uani 1 1 d . . . Cl1 Cl 0.43563(9) 2.10068(17) -0.14569(8) 0.0313(3) Uani 1 1 d . . . Cl2 Cl 0.58954(9) 1.73558(16) 0.08659(8) 0.0291(4) Uani 1 1 d . . . O1 O 0.2760(2) 1.4531(6) 0.1829(2) 0.0275(9) Uani 1 1 d . . . H1A H 0.2467 1.5490 0.1708 0.041 Uiso 1 1 d . . . H1B H 0.2747 1.4472 0.2294 0.041 Uiso 1 1 d . . . O2 O 0.2861(3) 1.0382(6) 0.0171(2) 0.0297(10) Uani 1 1 d . . . H2A H 0.3011 1.0434 -0.0281 0.045 Uiso 1 1 d . . . H2B H 0.2332 0.9722 0.0209 0.045 Uiso 1 1 d . . . O3 O 0.4718(3) 1.9604(6) -0.1061(3) 0.0428(11) Uani 1 1 d . . . O4 O 0.4161(3) 2.0553(7) -0.2151(2) 0.0503(12) Uani 1 1 d . . . O5 O 0.3469(3) 2.1589(6) -0.1130(2) 0.0414(10) Uani 1 1 d . . . O6 O 0.5084(3) 2.2299(5) -0.1430(3) 0.0450(11) Uani 1 1 d . . . O7 O 0.5424(3) 1.8862(6) 0.0667(3) 0.0484(13) Uani 1 1 d . . . O8 O 0.6832(3) 1.7670(5) 0.1156(3) 0.0435(12) Uani 1 1 d . . . O9 O 0.6025(3) 1.6312(6) 0.0262(2) 0.0506(12) Uani 1 1 d . . . O10 O 0.5301(3) 1.6473(5) 0.1349(3) 0.0415(11) Uani 1 1 d . . . O11 O 0.6934(3) 2.5575(6) -0.1719(2) 0.0492(12) Uani 1 1 d . . . H11A H 0.6477 2.6114 -0.1470 0.074 Uiso 1 1 d . . . H11B H 0.6962 2.4568 -0.1629 0.074 Uiso 1 1 d . . . O12 O 0.4931(3) 2.6390(6) -0.1718(2) 0.0429(10) Uani 1 1 d . . . H12A H 0.4959 2.7510 -0.1758 0.064 Uiso 1 1 d . . . H12B H 0.4885 2.6051 -0.1275 0.064 Uiso 1 1 d . . . N1 N 0.2758(3) 1.4264(6) 0.0280(2) 0.0215(10) Uani 1 1 d . . . N2 N 0.1304(3) 1.3159(6) -0.0183(2) 0.0251(10) Uani 1 1 d . . . H2C H 0.1111 1.2704 -0.0573 0.030 Uiso 1 1 calc R . . N3 N 0.1339(3) 1.2398(5) 0.0994(3) 0.0185(7) Uani 1 1 d . . . N4 N 0.1289(3) 1.1526(6) 0.2160(2) 0.0235(10) Uani 1 1 d . . . H4A H 0.1046 1.1859 0.2557 0.028 Uiso 1 1 calc R . . N5 N 0.2804(3) 1.0624(6) 0.1707(2) 0.0201(10) Uani 1 1 d . . . N6 N 0.2766(3) 1.6670(7) -0.0768(2) 0.0321(12) Uani 1 1 d . . . N7 N -0.0681(3) 1.2431(5) 0.1006(3) 0.0205(8) Uani 1 1 d . . . N8 N 0.2891(3) 0.8225(7) 0.2748(3) 0.0306(11) Uani 1 1 d . . . C1 C 0.3435(3) 1.5525(7) 0.0254(3) 0.0247(12) Uani 1 1 d . . . H1C H 0.3911 1.5604 0.0608 0.030 Uiso 1 1 calc R . . C2 C 0.3438(4) 1.6670(8) -0.0270(3) 0.0285(12) Uani 1 1 d . . . H2D H 0.3935 1.7492 -0.0281 0.034 Uiso 1 1 calc R . . C3 C 0.2081(4) 1.5502(9) -0.0731(3) 0.0330(14) Uani 1 1 d . . . H3A H 0.1582 1.5484 -0.1070 0.040 Uiso 1 1 calc R . . C4 C 0.2069(3) 1.4292(7) -0.0205(3) 0.0230(11) Uani 1 1 d . . . C5 C 0.0830(4) 1.2707(6) 0.0417(3) 0.0213(12) Uani 1 1 d . . . C6 C -0.0179(4) 1.2677(7) 0.0413(3) 0.0224(13) Uani 1 1 d . . . H6A H -0.0520 1.2830 -0.0009 0.027 Uiso 1 1 calc R . . C7 C -0.0196(4) 1.2140(8) 0.1577(3) 0.0223(12) Uani 1 1 d . . . H7A H -0.0537 1.1984 0.1999 0.027 Uiso 1 1 calc R . . C8 C 0.0826(4) 1.2060(7) 0.1570(3) 0.0223(11) Uani 1 1 d . . . C9 C 0.2105(3) 1.0508(7) 0.2183(3) 0.0232(11) Uani 1 1 d . . . C10 C 0.2165(3) 0.9305(7) 0.2708(3) 0.0253(12) Uani 1 1 d . . . H10A H 0.1666 0.9266 0.3048 0.030 Uiso 1 1 calc R . . C11 C 0.3566(4) 0.8320(7) 0.2252(3) 0.0290(13) Uani 1 1 d . . . H11C H 0.4090 0.7547 0.2257 0.035 Uiso 1 1 calc R . . C12 C 0.3532(4) 0.9482(7) 0.1739(3) 0.0284(13) Uani 1 1 d . . . H12C H 0.4027 0.9494 0.1397 0.034 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0132(3) 0.0246(3) 0.0242(3) 0.0016(2) 0.0015(3) -0.0002(2) Cl1 0.0242(6) 0.0400(7) 0.0297(7) 0.0019(6) -0.0012(6) -0.0032(5) Cl2 0.0204(5) 0.0278(6) 0.0392(9) 0.0032(6) 0.0019(5) 0.0011(5) O1 0.027(2) 0.028(2) 0.027(2) -0.0003(18) -0.0011(15) 0.0021(16) O2 0.026(2) 0.033(2) 0.030(2) -0.0018(19) 0.0056(16) -0.0053(17) O3 0.039(2) 0.044(3) 0.046(3) 0.005(2) -0.0035(19) 0.0034(19) O4 0.043(2) 0.076(4) 0.031(2) -0.006(2) 0.000(2) -0.007(2) O5 0.032(2) 0.061(3) 0.032(2) 0.006(2) 0.0039(17) 0.007(2) O6 0.042(2) 0.050(3) 0.043(3) 0.005(2) -0.004(2) -0.0174(19) O7 0.036(2) 0.039(3) 0.070(3) 0.017(2) 0.015(2) 0.012(2) O8 0.0263(19) 0.042(2) 0.062(4) 0.000(2) -0.010(2) -0.0042(18) O9 0.041(2) 0.061(3) 0.050(3) -0.015(2) -0.004(2) 0.015(2) O10 0.034(2) 0.037(2) 0.054(3) 0.011(2) 0.0063(18) -0.0062(19) O11 0.040(2) 0.065(3) 0.043(3) 0.001(2) -0.0009(19) 0.025(2) O12 0.035(2) 0.056(3) 0.038(2) -0.005(2) -0.0091(18) 0.011(2) N1 0.016(2) 0.023(3) 0.026(3) -0.003(2) 0.0008(16) 0.0020(17) N2 0.022(2) 0.038(3) 0.015(2) -0.0021(19) 0.0005(17) -0.005(2) N3 0.0165(16) 0.0222(19) 0.0168(18) -0.0011(15) 0.001(2) -0.0025(16) N4 0.0168(19) 0.033(3) 0.021(2) 0.000(2) 0.0029(16) 0.0054(18) N5 0.012(2) 0.023(3) 0.025(3) -0.001(2) 0.0032(15) -0.0003(17) N6 0.027(2) 0.040(3) 0.029(3) 0.007(2) 0.0010(18) -0.002(2) N7 0.0162(16) 0.0177(17) 0.028(2) -0.0012(16) 0.003(2) 0.0018(16) N8 0.025(2) 0.033(3) 0.034(3) 0.003(2) -0.002(2) -0.001(2) C1 0.012(2) 0.033(3) 0.030(3) -0.004(2) 0.001(2) -0.003(2) C2 0.023(3) 0.032(3) 0.030(3) 0.000(3) 0.005(2) -0.003(2) C3 0.021(3) 0.045(4) 0.032(4) 0.000(3) 0.003(2) 0.002(2) C4 0.019(2) 0.029(3) 0.021(3) 0.002(2) 0.0049(19) 0.000(2) C5 0.016(3) 0.021(3) 0.027(3) -0.005(2) 0.003(2) 0.000(2) C6 0.017(3) 0.027(3) 0.023(3) 0.004(2) -0.001(2) -0.001(2) C7 0.018(3) 0.026(3) 0.023(3) -0.001(3) 0.001(2) 0.001(2) C8 0.018(3) 0.023(3) 0.025(3) -0.003(2) 0.000(2) -0.002(2) C9 0.017(2) 0.028(3) 0.025(3) -0.005(2) -0.0006(19) 0.001(2) C10 0.020(3) 0.032(3) 0.024(3) 0.003(2) 0.003(2) 0.000(2) C11 0.026(3) 0.026(3) 0.035(3) 0.002(3) 0.003(2) 0.000(2) C12 0.022(3) 0.025(3) 0.038(3) -0.003(3) 0.003(2) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.004(5) . ? Cu1 N5 2.017(5) . ? Cu1 N3 2.029(4) . ? Cu1 N7 2.070(4) 3_575 ? Cu1 O1 2.305(4) . ? Cu1 O2 2.320(4) . ? Cl1 O4 1.418(5) . ? Cl1 O6 1.441(5) . ? Cl1 O3 1.449(5) . ? Cl1 O5 1.451(4) . ? Cl2 O7 1.424(5) . ? Cl2 O8 1.427(4) . ? Cl2 O10 1.430(4) . ? Cl2 O9 1.450(5) . ? N1 C4 1.334(7) . ? N1 C1 1.375(7) . ? N2 C5 1.381(7) . ? N2 C4 1.391(7) . ? N3 C5 1.342(7) . ? N3 C8 1.347(7) . ? N4 C8 1.378(7) . ? N4 C9 1.388(7) . ? N5 C9 1.336(7) . ? N5 C12 1.358(7) . ? N6 C3 1.331(8) . ? N6 C2 1.335(7) . ? N7 C7 1.313(8) . ? N7 C6 1.356(8) . ? N7 Cu1 2.070(4) 3_475 ? N8 C10 1.324(7) . ? N8 C11 1.339(7) . ? C1 C2 1.369(8) . ? C3 C4 1.406(8) . ? C5 C6 1.388(9) . ? C7 C8 1.406(8) . ? C9 C10 1.404(8) . ? C11 C12 1.363(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 N1 Cu1 N5 177.05(16) . . ? N1 Cu1 N3 88.76(18) . . ? N5 Cu1 N3 88.60(17) . . ? N1 Cu1 N7 90.89(18) . 3_575 ? N5 Cu1 N7 91.76(17) . 3_575 ? N3 Cu1 N7 179.47(17) . 3_575 ? N1 Cu1 O1 88.29(15) . . ? N5 Cu1 O1 93.0(2) . . ? N3 Cu1 O1 89.57(16) . . ? N7 Cu1 O1 90.02(16) 3_575 . ? N1 Cu1 O2 92.1(2) . . ? N5 Cu1 O2 86.57(15) . . ? N3 Cu1 O2 90.20(16) . . ? N7 Cu1 O2 90.22(16) 3_575 . ? O1 Cu1 O2 179.52(18) . . ? O4 Cl1 O6 110.5(3) . . ? O4 Cl1 O3 111.6(3) . . ? O6 Cl1 O3 107.5(3) . . ? O4 Cl1 O5 109.7(3) . . ? O6 Cl1 O5 109.7(3) . . ? O3 Cl1 O5 107.9(3) . . ? O7 Cl2 O8 111.6(3) . . ? O7 Cl2 O10 109.7(3) . . ? O8 Cl2 O10 110.2(3) . . ? O7 Cl2 O9 109.1(3) . . ? O8 Cl2 O9 108.0(3) . . ? O10 Cl2 O9 108.3(3) . . ? C4 N1 C1 116.2(5) . . ? C4 N1 Cu1 122.0(4) . . ? C1 N1 Cu1 121.8(4) . . ? C5 N2 C4 123.6(5) . . ? C5 N3 C8 117.0(4) . . ? C5 N3 Cu1 121.3(4) . . ? C8 N3 Cu1 121.7(4) . . ? C8 N4 C9 125.7(5) . . ? C9 N5 C12 116.9(5) . . ? C9 N5 Cu1 121.7(4) . . ? C12 N5 Cu1 121.4(3) . . ? C3 N6 C2 116.7(5) . . ? C7 N7 C6 118.7(4) . . ? C7 N7 Cu1 121.4(4) . 3_475 ? C6 N7 Cu1 119.9(4) . 3_475 ? C10 N8 C11 116.4(5) . . ? C2 C1 N1 121.5(5) . . ? N6 C2 C1 122.3(5) . . ? N6 C3 C4 122.2(5) . . ? N1 C4 N2 120.3(5) . . ? N1 C4 C3 120.9(5) . . ? N2 C4 C3 118.8(5) . . ? N3 C5 N2 120.3(5) . . ? N3 C5 C6 121.5(5) . . ? N2 C5 C6 118.1(5) . . ? N7 C6 C5 120.5(5) . . ? N7 C7 C8 120.5(5) . . ? N3 C8 N4 120.5(4) . . ? N3 C8 C7 121.6(5) . . ? N4 C8 C7 117.9(5) . . ? N5 C9 N4 121.2(5) . . ? N5 C9 C10 120.4(5) . . ? N4 C9 C10 118.3(5) . . ? N8 C10 C9 122.4(5) . . ? N8 C11 C12 122.6(5) . . ? N5 C12 C11 121.3(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.521 _refine_diff_density_min -0.874 _refine_diff_density_rms 0.226 data_ic10018 _database_code_depnum_ccdc_archive 'CCDC 273185' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H36 Cl4 Cu2 N14 O22' _chemical_formula_weight 1177.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 14.5271(2) _cell_length_b 14.3046(2) _cell_length_c 23.1894(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.2420(4) _cell_angle_gamma 90.00 _cell_volume 4602.30(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used all _cell_measurement_theta_min 1.47 _cell_measurement_theta_max 25.00 _exptl_crystal_description plate _exptl_crystal_colour 'pale green' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.700 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2392 _exptl_absorpt_coefficient_mu 1.251 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.728 _exptl_absorpt_correction_T_max 0.834 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'NONIUS KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 54609 _diffrn_reflns_av_R_equivalents 0.0655 _diffrn_reflns_av_sigmaI/netI 0.0418 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8102 _reflns_number_gt 5842 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.1249P)^2^+19.3330P] 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 SHELXL _refine_ls_extinction_coef 0.0041(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8102 _refine_ls_number_parameters 642 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1234 _refine_ls_R_factor_gt 0.0918 _refine_ls_wR_factor_ref 0.2728 _refine_ls_wR_factor_gt 0.2453 _refine_ls_goodness_of_fit_ref 1.186 _refine_ls_restrained_S_all 1.187 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.001 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 -0.25694(5) -0.01775(6) 0.24428(4) 0.0349(3) Uani 1 1 d . . . Cu2 Cu -0.24353(6) 0.48411(6) 0.25456(4) 0.0383(3) Uani 1 1 d . . . O1 O -0.2149(4) -0.0180(3) 0.3353(3) 0.0458(13) Uani 1 1 d . . . H1 H -0.2113 -0.0652 0.3435 0.069 Uiso 1 1 d . . . H1' H -0.1378 -0.0039 0.3521 0.069 Uiso 1 1 d . . . O2 O -0.2849(4) 0.4829(4) 0.1640(3) 0.0500(14) Uani 1 1 d . . . H2 H -0.3146 0.4510 0.1441 0.075 Uiso 1 1 d . . . H2' H -0.2690 0.5324 0.1420 0.075 Uiso 1 1 d . . . N1 N -0.3962(4) -0.0283(4) 0.2422(3) 0.0332(13) Uani 1 1 d . . . N2 N -0.4441(4) 0.0656(4) 0.1553(3) 0.0374(14) Uani 1 1 d . . . H2A H -0.4730 0.1196 0.1444 0.045 Uiso 1 1 calc R . . N3 N -0.2998(4) -0.0107(4) 0.1541(3) 0.0363(14) Uani 1 1 d . . . N4 N -0.1583(4) -0.0875(4) 0.1505(3) 0.0468(16) Uani 1 1 d . . . H4A H -0.1439 -0.1409 0.1364 0.056 Uiso 1 1 calc R . . N5 N -0.1199(4) -0.0061(4) 0.2423(3) 0.0434(16) Uani 1 1 d . . . N6 N -0.5838(4) -0.0212(4) 0.2499(3) 0.0360(14) Uani 1 1 d . . . N7 N 0.0745(4) -0.0138(4) 0.2485(4) 0.0507(18) Uani 1 1 d . . . N8 N -0.2379(4) 0.3452(4) 0.2576(3) 0.0387(15) Uani 1 1 d . . . N9 N -0.2779(5) 0.3433(4) 0.3487(3) 0.0491(17) Uani 1 1 d . . . H9A H -0.3239 0.3233 0.3632 0.059 Uiso 1 1 calc R . . N10 N -0.1994(4) 0.4867(4) 0.3450(3) 0.0486(17) Uani 1 1 d . . . N11 N -0.1206(5) 0.6297(5) 0.3434(4) 0.077(3) Uani 1 1 d . . . H11A H -0.0611 0.6510 0.3556 0.093 Uiso 1 1 calc R . . N12 N -0.2499(4) 0.6226(4) 0.2539(3) 0.0397(15) Uani 1 1 d . . . N13 N -0.2646(4) 0.1523(4) 0.2494(3) 0.0414(15) Uani 1 1 d . . . N14 N -0.2399(4) 0.8170(4) 0.2447(3) 0.0452(16) Uani 1 1 d . . . C1 C -0.4234(5) -0.0783(5) 0.2841(3) 0.0398(17) Uani 1 1 d . . . H1A H -0.3771 -0.1162 0.3118 0.048 Uiso 1 1 calc R . . C2 C -0.5157(5) -0.0755(5) 0.2877(4) 0.0416(18) Uani 1 1 d . . . H2B H -0.5323 -0.1123 0.3173 0.050 Uiso 1 1 calc R . . C3 C -0.5577(5) 0.0247(5) 0.2078(3) 0.0342(16) Uani 1 1 d . . . H3A H -0.6041 0.0626 0.1802 0.041 Uiso 1 1 calc R . . C4 C -0.4639(5) 0.0199(4) 0.2023(3) 0.0305(15) Uani 1 1 d . . . C5 C -0.3827(5) 0.0348(5) 0.1233(4) 0.0400(17) Uani 1 1 d . . . C6 C -0.4089(6) 0.0507(6) 0.0621(4) 0.0481(19) Uani 1 1 d . . . H6A H -0.4626 0.0891 0.0428 0.058 Uiso 1 1 calc R . . C7 C -0.3538(6) 0.0083(6) 0.0293(4) 0.055(2) Uani 1 1 d . . . H7A H -0.3703 0.0165 -0.0132 0.066 Uiso 1 1 calc R . . C8 C -0.2760(6) -0.0449(6) 0.0587(4) 0.054(2) Uani 1 1 d . . . H8A H -0.2423 -0.0796 0.0364 0.065 Uiso 1 1 calc R . . C9 C -0.2467(5) -0.0480(5) 0.1208(4) 0.0431(18) Uani 1 1 d . . . C10 C -0.0904(5) -0.0500(5) 0.2008(4) 0.046(2) Uani 1 1 d . . . C11 C 0.0073(5) -0.0551(5) 0.2051(4) 0.049(2) Uani 1 1 d . . . H11B H 0.0262 -0.0897 0.1755 0.059 Uiso 1 1 calc R . . C12 C 0.0439(6) 0.0340(6) 0.2896(5) 0.064(3) Uani 1 1 d . . . H12A H 0.0895 0.0660 0.3214 0.077 Uiso 1 1 calc R . . C13 C -0.0511(6) 0.0371(5) 0.2863(4) 0.058(2) Uani 1 1 d . . . H13A H -0.0698 0.0712 0.3162 0.070 Uiso 1 1 calc R . . C14 C -0.2166(7) 0.2949(5) 0.2141(4) 0.058(2) Uani 1 1 d . . . H14A H -0.1929 0.3260 0.1852 0.069 Uiso 1 1 calc R . . C15 C -0.2285(7) 0.1998(5) 0.2107(4) 0.058(2) Uani 1 1 d . . . H15A H -0.2108 0.1663 0.1802 0.069 Uiso 1 1 calc R . . C16 C -0.2844(5) 0.2009(5) 0.2923(4) 0.0419(18) Uani 1 1 d . . . H16A H -0.3110 0.1697 0.3198 0.050 Uiso 1 1 calc R . . C17 C -0.2674(5) 0.2987(5) 0.2987(4) 0.0421(18) Uani 1 1 d . . . C18 C -0.2208(6) 0.4184(6) 0.3788(4) 0.051(2) Uani 1 1 d . . . C19 C -0.1907(7) 0.4169(8) 0.4406(4) 0.071(3) Uani 1 1 d . . . H19A H -0.2107 0.3689 0.4626 0.085 Uiso 1 1 calc R . . C20 C -0.1292(8) 0.4891(10) 0.4702(5) 0.093(5) Uani 1 1 d . . . H20A H -0.1045 0.4892 0.5130 0.111 Uiso 1 1 calc R . . C21 C -0.1051(7) 0.5587(8) 0.4377(5) 0.079(4) Uani 1 1 d . . . H21A H -0.0631 0.6077 0.4570 0.095 Uiso 1 1 calc R . . C22 C -0.1430(6) 0.5562(6) 0.3762(4) 0.061(3) Uani 1 1 d . . . C23 C -0.1815(5) 0.6719(5) 0.2943(4) 0.055(2) Uani 1 1 d . . . C24 C -0.1758(5) 0.7705(5) 0.2859(5) 0.057(3) Uani 1 1 d . . . H24A H -0.1227 0.8037 0.3116 0.069 Uiso 1 1 calc R . . C25 C -0.3115(6) 0.7664(5) 0.2073(4) 0.0458(19) Uani 1 1 d . . . H25A H -0.3606 0.7978 0.1772 0.055 Uiso 1 1 calc R . . C26 C -0.3155(5) 0.6714(5) 0.2113(4) 0.0417(18) Uani 1 1 d . . . H26A H -0.3662 0.6387 0.1832 0.050 Uiso 1 1 calc R . . Cl1 Cl -0.01550(14) -0.26030(13) 0.09498(10) 0.0466(5) Uani 1 1 d . . . O3 O -0.0465(5) -0.1699(4) 0.0721(3) 0.0624(16) Uani 1 1 d . . . O4 O 0.0806(5) -0.2723(5) 0.1081(5) 0.110(3) Uani 1 1 d . . . O5 O -0.0641(8) -0.3327(7) 0.0592(6) 0.160(5) Uani 1 1 d . . . O6 O -0.0404(10) -0.2679(6) 0.1503(5) 0.149(5) Uani 1 1 d . . . Cl2 Cl -0.33830(16) 0.77152(14) -0.08895(12) 0.0614(6) Uani 1 1 d . . . O7 O -0.3226(8) 0.7790(6) -0.1479(4) 0.107(3) Uani 1 1 d . . . O8 O -0.2484(7) 0.7599(6) -0.0441(6) 0.147(5) Uani 1 1 d . . . O9 O -0.3933(9) 0.6903(8) -0.0889(4) 0.145(5) Uani 1 1 d . . . O10 O -0.3789(7) 0.8535(6) -0.0757(3) 0.110(3) Uani 1 1 d . . . Cl3 Cl -0.1094(2) -0.7867(2) 0.09581(14) 0.0587(8) Uani 0.75 1 d P A 1 Cl3' Cl -0.1053(6) -0.7134(7) 0.0850(3) 0.049(2) Uani 0.25 1 d PD A 2 O11 O -0.1991(7) -0.7304(9) 0.0763(4) 0.131(4) Uani 1 1 d . . . O12 O -0.0560(6) -0.7363(9) 0.1484(4) 0.141(5) Uani 1 1 d . . . O13 O -0.0523(9) -0.7862(7) 0.0578(5) 0.135(4) Uani 1 1 d D . . O14 O -0.1289(9) -0.8790(7) 0.1052(5) 0.105(4) Uani 0.75 1 d P A 1 O14' O -0.090(5) -0.6377(14) 0.050(3) 0.25(3) Uiso 0.25 1 d PD A 2 Cl4 Cl -0.5370(3) 0.7713(4) 0.0707(2) 0.0458(12) Uani 0.50 1 d P B 1 O15 O -0.5508(15) 0.7179(16) 0.1195(9) 0.093(7) Uiso 0.50 1 d P B 1 O16 O -0.6109(13) 0.7684(12) 0.0161(8) 0.100(5) Uiso 0.50 1 d P B 1 O17 O -0.4584(19) 0.7312(18) 0.0623(11) 0.109(8) Uiso 0.50 1 d P B 1 O18 O -0.5204(10) 0.8661(10) 0.0965(6) 0.070(4) Uiso 0.50 1 d P B 1 Cl4' Cl -0.5398(3) 0.7652(4) 0.1040(4) 0.0567(14) Uani 0.50 1 d P C 2 O15' O -0.5308(11) 0.7812(11) 0.1682(7) 0.084(4) Uiso 0.50 1 d P C 2 O16' O -0.5104(12) 0.6726(12) 0.1047(7) 0.083(4) Uiso 0.50 1 d P C 2 O17' O -0.4821(12) 0.8289(12) 0.0837(7) 0.084(4) Uiso 0.50 1 d P C 2 O18' O -0.6412(8) 0.7706(8) 0.0665(5) 0.052(3) Uiso 0.50 1 d P C 2 O19 O -0.3150(8) 0.0524(9) 0.4017(5) 0.081(3) Uiso 0.63 1 d PD D 1 H19 H -0.3297 0.0189 0.4274 0.121 Uiso 0.63 1 calc PR D 1 O19' O -0.2724(15) 0.0415(14) 0.4651(9) 0.080(5) Uiso 0.38 1 d PD D 2 H19' H -0.2593 -0.0147 0.4605 0.120 Uiso 0.38 1 calc PR D 2 C27 C -0.2248(8) 0.1022(8) 0.4306(7) 0.117(5) Uani 1 1 d D . . H27A H -0.2078 0.0922 0.4749 0.175 Uiso 0.63 1 d P E 1 H27B H -0.2339 0.1689 0.4223 0.175 Uiso 0.63 1 d P F 1 H27C H -0.1736 0.0778 0.4159 0.175 Uiso 0.63 1 d P G 1 H27D H -0.1771 0.1408 0.4596 0.175 Uiso 0.38 1 d P H 2 H27E H -0.2733 0.1421 0.4037 0.175 Uiso 0.38 1 d P I 2 H27F H -0.1934 0.0634 0.4077 0.175 Uiso 0.38 1 d P J 2 O20 O 0.1002(11) -0.6283(10) 0.0798(5) 0.194(7) Uani 1 1 d . . . H20 H 0.0943 -0.5696 0.0868 0.291 Uiso 1 1 d . . . H20' H 0.1441 -0.6249 0.0621 0.291 Uiso 1 1 d . . . O21 O -0.2627(9) 0.6279(10) 0.0863(5) 0.176(6) Uani 1 1 d . . . H21 H -0.3111 0.6525 0.0570 0.264 Uiso 1 1 d . . . H21' H -0.2383 0.5807 0.0779 0.264 Uiso 1 1 d . . . O22 O -0.6014(10) -0.1405(12) 0.4097(6) 0.208(8) Uani 1 1 d . . . H22 H -0.5843 -0.1689 0.4485 0.312 Uiso 1 1 d . . . H22' H -0.6141 -0.2053 0.3892 0.312 Uiso 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 0.0229(5) 0.0288(5) 0.0573(6) -0.0085(4) 0.0187(4) -0.0025(3) Cu2 0.0320(5) 0.0237(5) 0.0644(7) -0.0142(4) 0.0223(4) -0.0037(3) O1 0.035(3) 0.032(3) 0.069(4) -0.001(2) 0.014(3) 0.003(2) O2 0.052(3) 0.040(3) 0.066(4) -0.016(3) 0.029(3) -0.011(2) N1 0.023(3) 0.032(3) 0.051(3) -0.003(3) 0.019(3) 0.000(2) N2 0.033(3) 0.033(3) 0.053(4) 0.008(3) 0.022(3) 0.007(2) N3 0.028(3) 0.028(3) 0.059(4) -0.010(3) 0.024(3) -0.006(2) N4 0.035(3) 0.035(3) 0.077(5) -0.026(3) 0.027(3) -0.007(3) N5 0.031(3) 0.029(3) 0.078(5) -0.017(3) 0.029(3) -0.007(3) N6 0.029(3) 0.034(3) 0.050(4) 0.008(3) 0.018(3) 0.004(2) N7 0.032(3) 0.029(3) 0.097(6) -0.021(3) 0.027(4) -0.006(3) N8 0.036(3) 0.024(3) 0.068(4) -0.011(3) 0.035(3) -0.007(2) N9 0.064(4) 0.035(3) 0.058(4) -0.009(3) 0.034(3) 0.005(3) N10 0.035(3) 0.030(3) 0.073(5) -0.016(3) 0.004(3) 0.015(3) N11 0.033(4) 0.029(4) 0.136(7) -0.023(4) -0.027(4) 0.007(3) N12 0.027(3) 0.027(3) 0.067(4) -0.017(3) 0.016(3) -0.006(2) N13 0.042(3) 0.030(3) 0.061(4) -0.009(3) 0.028(3) -0.006(3) N14 0.032(3) 0.028(3) 0.077(5) -0.015(3) 0.019(3) -0.004(3) C1 0.032(4) 0.031(4) 0.056(5) 0.012(3) 0.013(3) 0.006(3) C2 0.035(4) 0.034(4) 0.062(5) 0.009(3) 0.025(4) 0.007(3) C3 0.027(3) 0.031(4) 0.046(4) 0.006(3) 0.014(3) 0.002(3) C4 0.028(3) 0.024(3) 0.044(4) -0.004(3) 0.019(3) 0.001(3) C5 0.038(4) 0.032(4) 0.057(5) -0.004(3) 0.025(4) -0.009(3) C6 0.044(4) 0.052(5) 0.055(5) 0.000(4) 0.025(4) -0.005(4) C7 0.053(5) 0.067(6) 0.057(5) -0.009(4) 0.034(4) -0.018(4) C8 0.049(5) 0.057(5) 0.073(6) -0.020(4) 0.042(5) -0.010(4) C9 0.035(4) 0.037(4) 0.068(5) -0.016(4) 0.032(4) -0.013(3) C10 0.040(4) 0.023(3) 0.090(6) -0.011(4) 0.039(4) -0.009(3) C11 0.037(4) 0.023(4) 0.095(6) -0.015(4) 0.034(4) -0.006(3) C12 0.030(4) 0.045(5) 0.122(8) -0.035(5) 0.029(5) -0.008(4) C13 0.038(4) 0.037(4) 0.101(7) -0.039(5) 0.025(4) -0.005(4) C14 0.074(6) 0.027(4) 0.100(7) -0.019(4) 0.069(6) -0.013(4) C15 0.077(6) 0.027(4) 0.094(7) -0.025(4) 0.066(5) -0.019(4) C16 0.040(4) 0.033(4) 0.061(5) -0.003(3) 0.028(4) 0.004(3) C17 0.038(4) 0.033(4) 0.057(5) -0.007(4) 0.018(4) 0.010(3) C18 0.056(5) 0.040(5) 0.055(5) -0.013(4) 0.011(4) 0.021(4) C19 0.069(6) 0.081(7) 0.062(6) -0.013(5) 0.018(5) 0.039(6) C20 0.067(7) 0.119(11) 0.071(7) -0.055(8) -0.011(6) 0.050(7) C21 0.058(6) 0.066(7) 0.090(8) -0.040(6) -0.012(6) 0.028(5) C22 0.043(5) 0.042(5) 0.084(7) -0.027(5) -0.003(5) 0.018(4) C23 0.021(3) 0.033(4) 0.105(7) -0.021(4) 0.009(4) -0.001(3) C24 0.026(4) 0.028(4) 0.113(8) -0.025(4) 0.013(4) -0.007(3) C25 0.047(4) 0.034(4) 0.061(5) -0.010(4) 0.023(4) -0.012(3) C26 0.037(4) 0.033(4) 0.057(5) -0.008(3) 0.016(4) -0.011(3) Cl1 0.0448(10) 0.0347(10) 0.0628(12) -0.0022(9) 0.0198(9) 0.0057(8) O3 0.078(4) 0.054(4) 0.058(4) 0.014(3) 0.025(3) 0.025(3) O4 0.048(4) 0.074(5) 0.199(10) 0.027(6) 0.021(5) 0.015(4) O5 0.138(9) 0.083(7) 0.204(11) -0.073(7) -0.033(8) 0.004(6) O6 0.251(14) 0.079(6) 0.182(10) 0.063(6) 0.165(10) 0.067(7) Cl2 0.0549(13) 0.0397(11) 0.0852(16) 0.0001(10) 0.0140(12) -0.0004(9) O7 0.155(8) 0.082(6) 0.114(6) -0.021(5) 0.084(6) -0.005(5) O8 0.106(7) 0.082(6) 0.191(11) -0.002(6) -0.051(7) 0.032(5) O9 0.177(11) 0.147(9) 0.108(7) -0.031(6) 0.040(7) -0.102(9) O10 0.146(8) 0.105(6) 0.062(4) -0.021(4) 0.003(5) 0.075(6) Cl3 0.0662(19) 0.059(2) 0.0588(18) -0.0078(15) 0.0301(15) -0.0158(16) Cl3' 0.039(4) 0.072(6) 0.030(4) 0.001(4) 0.004(3) 0.019(4) O11 0.082(6) 0.208(12) 0.088(6) 0.032(7) 0.003(5) 0.014(7) O12 0.055(5) 0.263(14) 0.109(7) -0.080(8) 0.030(5) -0.013(6) O13 0.192(11) 0.097(7) 0.142(8) -0.040(6) 0.089(8) -0.036(7) O14 0.140(10) 0.066(6) 0.127(9) -0.023(6) 0.069(8) -0.040(7) Cl4 0.038(2) 0.063(3) 0.033(2) -0.008(2) 0.007(2) -0.0008(19) Cl4' 0.036(2) 0.061(4) 0.072(4) -0.025(4) 0.015(3) 0.001(2) C27 0.073(8) 0.085(9) 0.169(14) -0.051(9) -0.001(8) 0.019(7) O20 0.254(15) 0.210(13) 0.135(9) -0.074(9) 0.085(9) -0.190(12) O21 0.213(12) 0.216(13) 0.145(9) -0.060(9) 0.122(9) -0.142(11) O22 0.179(12) 0.280(18) 0.200(12) 0.143(13) 0.111(10) 0.151(13) _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 2.000(6) . ? Cu1 N5 2.012(6) . ? Cu1 N1 2.015(5) . ? Cu1 O1 2.015(6) . ? Cu1 N14 2.376(6) 1_545 ? Cu1 N13 2.440(6) . ? Cu2 N12 1.983(6) . ? Cu2 N8 1.989(6) . ? Cu2 N10 2.003(7) . ? Cu2 O2 2.006(6) . ? Cu2 N7 2.478(6) 2 ? N1 C4 1.326(9) . ? N1 C1 1.357(9) . ? N2 C4 1.372(9) . ? N2 C5 1.390(9) . ? N3 C9 1.352(9) . ? N3 C5 1.370(10) . ? N4 C9 1.384(10) . ? N4 C10 1.393(10) . ? N5 C10 1.323(10) . ? N5 C13 1.348(10) . ? N6 C3 1.322(9) . ? N6 C2 1.356(9) . ? N7 C11 1.315(10) . ? N7 C12 1.351(11) . ? N7 Cu2 2.478(6) 2_545 ? N8 C17 1.333(10) . ? N8 C14 1.347(9) . ? N9 C17 1.371(9) . ? N9 C18 1.410(10) . ? N10 C18 1.346(11) . ? N10 C22 1.353(11) . ? N11 C23 1.358(11) . ? N11 C22 1.392(13) . ? N12 C26 1.346(10) . ? N12 C23 1.346(9) . ? N13 C16 1.313(9) . ? N13 C15 1.350(10) . ? N14 C24 1.302(11) . ? N14 C25 1.351(10) . ? N14 Cu1 2.376(6) 1_565 ? C1 C2 1.368(10) . ? C3 C4 1.407(9) . ? C5 C6 1.375(11) . ? C6 C7 1.395(12) . ? C7 C8 1.366(13) . ? C8 C9 1.378(12) . ? C10 C11 1.395(10) . ? C12 C13 1.360(11) . ? C14 C15 1.371(10) . ? C16 C17 1.421(10) . ? C18 C19 1.368(12) . ? C19 C20 1.405(17) . ? C20 C21 1.357(18) . ? C21 C22 1.369(14) . ? C23 C24 1.430(11) . ? C25 C26 1.363(10) . ? Cl1 O4 1.349(7) . ? Cl1 O5 1.382(8) . ? Cl1 O3 1.419(6) . ? Cl1 O6 1.437(9) . ? Cl2 O10 1.387(7) . ? Cl2 O9 1.410(9) . ? Cl2 O8 1.418(9) . ? Cl2 O7 1.455(8) . ? Cl3 O13 1.378(11) . ? Cl3 O14 1.382(10) . ? Cl3 O12 1.430(9) . ? Cl3 O11 1.484(10) . ? Cl3' O11 1.339(13) . ? Cl3' O14' 1.410(10) . ? Cl3' O12 1.467(13) . ? Cl3' O13 1.537(13) . ? Cl4 O17 1.34(3) . ? Cl4 O16 1.397(18) . ? Cl4 O15 1.43(2) . ? Cl4 O18 1.474(16) . ? Cl4' O16' 1.390(18) . ? Cl4' O17' 1.410(18) . ? Cl4' O15' 1.473(17) . ? Cl4' O18' 1.474(12) . ? O19 C27 1.467(9) . ? O19' C27 1.483(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 N3 Cu1 N5 88.6(3) . . ? N3 Cu1 N1 88.8(2) . . ? N5 Cu1 N1 177.4(3) . . ? N3 Cu1 O1 177.2(2) . . ? N5 Cu1 O1 91.7(2) . . ? N1 Cu1 O1 90.9(2) . . ? N3 Cu1 N14 93.1(2) . 1_545 ? N5 Cu1 N14 88.8(2) . 1_545 ? N1 Cu1 N14 91.6(2) . 1_545 ? O1 Cu1 N14 89.7(2) . 1_545 ? N3 Cu1 N13 89.8(2) . . ? N5 Cu1 N13 88.8(2) . . ? N1 Cu1 N13 90.9(2) . . ? O1 Cu1 N13 87.4(2) . . ? N14 Cu1 N13 176.2(2) 1_545 . ? N12 Cu2 N8 178.3(2) . . ? N12 Cu2 N10 89.4(3) . . ? N8 Cu2 N10 89.1(3) . . ? N12 Cu2 O2 90.1(2) . . ? N8 Cu2 O2 91.4(2) . . ? N10 Cu2 O2 178.7(2) . . ? N12 Cu2 N7 91.9(2) . 2 ? N8 Cu2 N7 89.0(2) . 2 ? N10 Cu2 N7 91.0(3) . 2 ? O2 Cu2 N7 87.8(2) . 2 ? C4 N1 C1 117.4(5) . . ? C4 N1 Cu1 120.7(4) . . ? C1 N1 Cu1 121.7(5) . . ? C4 N2 C5 126.4(6) . . ? C9 N3 C5 117.0(7) . . ? C9 N3 Cu1 121.5(5) . . ? C5 N3 Cu1 121.5(5) . . ? C9 N4 C10 125.6(6) . . ? C10 N5 C13 116.2(6) . . ? C10 N5 Cu1 120.9(5) . . ? C13 N5 Cu1 122.5(5) . . ? C3 N6 C2 116.6(6) . . ? C11 N7 C12 116.3(6) . . ? C11 N7 Cu2 119.3(5) . 2_545 ? C12 N7 Cu2 124.2(5) . 2_545 ? C17 N8 C14 117.6(6) . . ? C17 N8 Cu2 120.3(5) . . ? C14 N8 Cu2 121.5(5) . . ? C17 N9 C18 125.2(7) . . ? C18 N10 C22 115.4(8) . . ? C18 N10 Cu2 122.6(5) . . ? C22 N10 Cu2 121.9(7) . . ? C23 N11 C22 126.4(7) . . ? C26 N12 C23 117.1(7) . . ? C26 N12 Cu2 123.1(5) . . ? C23 N12 Cu2 119.6(5) . . ? C16 N13 C15 116.9(7) . . ? C16 N13 Cu1 126.0(5) . . ? C15 N13 Cu1 115.9(5) . . ? C24 N14 C25 116.4(7) . . ? C24 N14 Cu1 124.2(5) . 1_565 ? C25 N14 Cu1 118.1(5) . 1_565 ? N1 C1 C2 121.8(6) . . ? N6 C2 C1 121.2(7) . . ? N6 C3 C4 122.7(6) . . ? N1 C4 N2 120.9(6) . . ? N1 C4 C3 120.0(6) . . ? N2 C4 C3 119.1(6) . . ? N3 C5 C6 123.2(7) . . ? N3 C5 N2 118.4(7) . . ? C6 C5 N2 118.4(7) . . ? C5 C6 C7 117.6(8) . . ? C8 C7 C6 119.6(8) . . ? C7 C8 C9 119.6(7) . . ? N3 C9 C8 122.2(7) . . ? N3 C9 N4 118.7(7) . . ? C8 C9 N4 119.1(7) . . ? N5 C10 N4 119.3(6) . . ? N5 C10 C11 121.0(7) . . ? N4 C10 C11 119.6(7) . . ? N7 C11 C10 122.7(7) . . ? N7 C12 C13 121.1(8) . . ? N5 C13 C12 122.7(8) . . ? N8 C14 C15 121.3(7) . . ? N13 C15 C14 121.9(7) . . ? N13 C16 C17 122.0(7) . . ? N8 C17 N9 120.9(7) . . ? N8 C17 C16 119.9(7) . . ? N9 C17 C16 119.1(7) . . ? N10 C18 C19 124.4(9) . . ? N10 C18 N9 118.0(7) . . ? C19 C18 N9 117.6(9) . . ? C18 C19 C20 117.3(12) . . ? C21 C20 C19 119.9(11) . . ? C20 C21 C22 118.0(10) . . ? N10 C22 C21 124.7(11) . . ? N10 C22 N11 117.8(8) . . ? C21 C22 N11 117.6(9) . . ? N12 C23 N11 121.0(7) . . ? N12 C23 C24 118.9(8) . . ? N11 C23 C24 120.2(7) . . ? N14 C24 C23 123.1(7) . . ? N14 C25 C26 122.0(8) . . ? N12 C26 C25 122.1(7) . . ? O4 Cl1 O5 110.5(6) . . ? O4 Cl1 O3 113.1(5) . . ? O5 Cl1 O3 114.2(6) . . ? O4 Cl1 O6 107.8(7) . . ? O5 Cl1 O6 105.1(8) . . ? O3 Cl1 O6 105.5(4) . . ? O10 Cl2 O9 114.7(8) . . ? O10 Cl2 O8 107.2(6) . . ? O9 Cl2 O8 107.5(7) . . ? O10 Cl2 O7 109.9(5) . . ? O9 Cl2 O7 108.0(6) . . ? O8 Cl2 O7 109.3(8) . . ? O13 Cl3 O14 107.2(7) . . ? O13 Cl3 O12 105.4(6) . . ? O14 Cl3 O12 115.6(8) . . ? O13 Cl3 O11 116.3(7) . . ? O14 Cl3 O11 111.3(7) . . ? O12 Cl3 O11 101.0(6) . . ? O11 Cl3' O14' 113(3) . . ? O11 Cl3' O12 106.4(8) . . ? O14' Cl3' O12 129(3) . . ? O11 Cl3' O13 115.3(10) . . ? O14' Cl3' O13 95.6(9) . . ? O12 Cl3' O13 96.0(8) . . ? Cl3' O11 Cl3 44.8(5) . . ? Cl3 O12 Cl3' 43.9(5) . . ? Cl3 O13 Cl3' 43.2(5) . . ? O17 Cl4 O16 108.3(13) . . ? O17 Cl4 O15 102.3(14) . . ? O16 Cl4 O15 116.9(12) . . ? O17 Cl4 O18 114.1(13) . . ? O16 Cl4 O18 112.7(10) . . ? O15 Cl4 O18 102.4(11) . . ? O16' Cl4' O17' 114.2(11) . . ? O16' Cl4' O15' 101.6(11) . . ? O17' Cl4' O15' 110.7(10) . . ? O16' Cl4' O18' 107.9(8) . . ? O17' Cl4' O18' 111.0(10) . . ? O15' Cl4' O18' 111.2(8) . . ? O19 C27 O19' 57.7(10) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.874 _refine_diff_density_min -0.645 _refine_diff_density_rms 0.236 data_ic10358 _database_code_depnum_ccdc_archive 'CCDC 273186' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H32 Cl4 Cu N8 Ni O28' _chemical_formula_weight 1000.51 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' Ni Ni 0.3393 1.1124 '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 P4(3)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 11.0763(2) _cell_length_b 11.0763(2) _cell_length_c 27.4307(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3365.32(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used all _cell_measurement_theta_min 1.98 _cell_measurement_theta_max 27.50 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.975 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2036 _exptl_absorpt_coefficient_mu 1.627 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.451 _exptl_absorpt_correction_T_max 0.862 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'NONIUS KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21483 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3867 _reflns_number_gt 3167 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0685P)^2^+3.0460P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(2) _refine_ls_number_reflns 3867 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1201 _refine_ls_wR_factor_gt 0.1121 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 -0.48391(4) -0.48391(4) 0.0000 0.02623(16) Uani 1 2 d S . . Ni1 Ni -0.02836(5) -0.02836(5) 0.0000 0.0386(2) Uani 1 2 d S . . O1 O -0.6109(2) -0.6109(2) 0.0000 0.0352(8) Uani 1 2 d S . . H1A H -0.6097 -0.7000 0.0086 0.053 Uiso 1 1 d . . . O2 O -0.3438(3) -0.6302(3) 0.00855(11) 0.0512(8) Uani 1 1 d . . . H2A H -0.3733 -0.6971 0.0223 0.077 Uiso 1 1 d . . . H2B H -0.3162 -0.6482 -0.0212 0.077 Uiso 1 1 d . . . O3 O 0.1109(6) 0.1109(6) 0.0000 0.101(2) Uani 1 2 d S . . H3A H 0.1057 0.1590 0.0314 0.152 Uiso 1 1 d . . . O4 O 0.1028(3) -0.1500(3) -0.00474(10) 0.0528(9) Uani 1 1 d . . . H4A H 0.0980 -0.2110 0.0046 0.079 Uiso 1 1 d . . . H4B H 0.1794 -0.1332 -0.0126 0.079 Uiso 1 1 d . . . N1 N -0.4972(3) -0.4661(3) 0.07312(10) 0.0256(6) Uani 1 1 d . . . N2 N -0.2937(3) -0.4065(3) 0.08039(10) 0.0294(7) Uani 1 1 d . . . N3 N -0.3540(2) -0.3540(2) 0.0000 0.0218(8) Uani 1 2 d S . . N4 N -0.5154(3) -0.4649(3) 0.17436(11) 0.0318(7) Uani 1 1 d . . . N5 N -0.1755(3) -0.1755(3) 0.0000 0.0272(9) Uani 1 2 d S . . C1 C -0.6032(3) -0.4878(3) 0.09593(12) 0.0292(8) Uani 1 1 d . . . H1B H -0.6730 -0.5041 0.0769 0.035 Uiso 1 1 calc R . . C2 C -0.6128(4) -0.4871(3) 0.14576(13) 0.0305(8) Uani 1 1 d . . . H2C H -0.6889 -0.5023 0.1605 0.037 Uiso 1 1 calc R . . C3 C -0.4116(4) -0.4415(4) 0.15193(12) 0.0329(9) Uani 1 1 d . . . H3B H -0.3417 -0.4262 0.1710 0.040 Uiso 1 1 calc R . . C4 C -0.4020(3) -0.4386(3) 0.10089(12) 0.0277(8) Uani 1 1 d . . . C5 C -0.2792(3) -0.3378(3) 0.03796(12) 0.0256(7) Uani 1 1 d . . . C6 C -0.1877(3) -0.2523(3) 0.03707(13) 0.0277(8) Uani 1 1 d . . . H6A H -0.1325 -0.2483 0.0635 0.033 Uiso 1 1 calc R . . Cl1 Cl 0.14354(12) 0.27114(12) 0.12028(5) 0.0559(3) Uani 1 1 d . . . O5 O 0.2217(5) 0.1755(5) 0.1100(3) 0.164(4) Uani 1 1 d . . . O6 O 0.1750(6) 0.3206(6) 0.16653(18) 0.130(3) Uani 1 1 d . . . O7 O 0.1562(5) 0.3636(4) 0.08542(16) 0.0876(15) Uani 1 1 d . . . O8 O 0.0227(3) 0.2279(3) 0.12246(14) 0.0635(10) Uani 1 1 d . . . Cl2 Cl -0.51805(11) -1.12079(9) 0.09133(4) 0.0437(3) Uani 1 1 d . . . O9 O -0.4755(4) -1.1078(4) 0.04333(13) 0.0706(11) Uani 1 1 d . . . O10 O -0.6149(4) -1.2058(4) 0.09212(16) 0.0813(13) Uani 1 1 d . . . O11 O -0.5652(4) -1.0105(3) 0.11015(16) 0.0696(11) Uani 1 1 d . . . O12 O -0.4233(5) -1.1661(5) 0.12093(16) 0.0952(16) Uani 1 1 d . . . O13 O -0.5873(5) -0.8276(4) 0.21491(19) 0.0970(16) Uani 1 1 d . . . H13A H -0.6632 -0.8494 0.2114 0.146 Uiso 1 1 d . . . H13B H -0.5296 -0.8798 0.2022 0.146 Uiso 1 1 d . . . O14 O -0.5836(7) -0.8432(5) 0.0254(2) 0.143(3) Uani 1 1 d . . . H14A H -0.6628 -0.8618 0.0301 0.214 Uiso 1 1 d . . . H14B H -0.5458 -0.8278 0.0538 0.214 Uiso 1 1 d . . . O15 O -0.3878(7) -1.1250(6) 0.22212(17) 0.124(2) Uani 1 1 d . . . H15A H -0.4462 -1.1037 0.2007 0.186 Uiso 1 1 d . . . H15B H -0.3862 -1.0859 0.2517 0.186 Uiso 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 0.0324(2) 0.0324(2) 0.0138(3) -0.00038(16) 0.00038(16) -0.0005(3) Ni1 0.0524(3) 0.0524(3) 0.0109(3) 0.00057(18) -0.00057(18) 0.0215(4) O1 0.0413(13) 0.0413(13) 0.0231(17) -0.0023(13) 0.0023(13) -0.0073(17) O2 0.079(2) 0.0391(17) 0.0359(16) -0.0005(13) 0.0030(15) 0.0045(16) O3 0.138(4) 0.138(4) 0.028(3) 0.000(2) 0.000(2) 0.049(5) O4 0.0510(19) 0.085(2) 0.0228(14) -0.0004(15) -0.0007(14) 0.0304(17) N1 0.0309(16) 0.0295(15) 0.0165(13) 0.0001(11) 0.0026(11) 0.0001(12) N2 0.0332(17) 0.0407(18) 0.0143(14) 0.0060(13) 0.0002(12) -0.0021(14) N3 0.0255(12) 0.0255(12) 0.0143(17) -0.0008(12) 0.0008(12) 0.0029(16) N4 0.0435(18) 0.0355(17) 0.0163(13) -0.0038(12) 0.0039(12) -0.0093(14) N5 0.0301(14) 0.0301(14) 0.021(2) -0.0037(13) 0.0037(13) -0.0014(18) C1 0.0332(18) 0.034(2) 0.0209(16) -0.0022(15) 0.0026(14) -0.0004(16) C2 0.039(2) 0.0288(19) 0.0239(17) -0.0028(15) 0.0064(15) -0.0029(16) C3 0.043(2) 0.039(2) 0.0165(17) 0.0010(14) -0.0002(15) -0.0092(17) C4 0.037(2) 0.0303(19) 0.0160(16) 0.0011(13) -0.0007(14) -0.0015(15) C5 0.0325(18) 0.0318(18) 0.0124(15) 0.0000(13) 0.0029(14) 0.0046(15) C6 0.034(2) 0.034(2) 0.0151(16) -0.0013(14) 0.0000(14) 0.0031(15) Cl1 0.0568(8) 0.0476(6) 0.0632(7) 0.0085(6) -0.0017(6) -0.0190(6) O5 0.085(4) 0.062(3) 0.345(11) 0.006(4) 0.094(5) -0.004(3) O6 0.149(6) 0.166(6) 0.074(3) 0.025(4) -0.047(3) -0.098(5) O7 0.100(3) 0.088(3) 0.074(3) 0.034(2) -0.003(2) -0.043(3) O8 0.054(2) 0.057(2) 0.080(3) 0.0038(18) 0.0025(18) -0.0254(18) Cl2 0.0553(6) 0.0373(5) 0.0386(5) 0.0055(4) 0.0145(5) 0.0093(5) O9 0.082(3) 0.085(3) 0.0445(19) 0.0095(18) 0.0302(19) 0.003(2) O10 0.089(3) 0.065(3) 0.090(3) -0.003(2) 0.044(3) -0.023(2) O11 0.082(3) 0.048(2) 0.079(3) -0.0042(18) 0.023(2) 0.020(2) O12 0.109(4) 0.096(3) 0.081(3) 0.001(3) -0.029(3) 0.055(3) O13 0.116(4) 0.059(3) 0.116(4) -0.003(3) 0.044(3) 0.002(3) O14 0.163(6) 0.100(4) 0.165(6) 0.080(4) -0.059(5) -0.041(4) O15 0.181(6) 0.117(4) 0.074(3) 0.034(3) -0.030(4) -0.045(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 O1 1.989(4) . ? Cu1 N1 2.021(3) 7 ? Cu1 N1 2.021(3) . ? Cu1 N3 2.035(4) . ? Cu1 O2 2.256(3) 7 ? Cu1 O2 2.256(3) . ? Ni1 O4 1.986(3) . ? Ni1 O4 1.986(3) 7 ? Ni1 N4 2.081(3) 3_454 ? Ni1 N4 2.081(3) 6_545 ? Ni1 O3 2.182(9) . ? Ni1 N5 2.305(4) . ? N1 C4 1.336(5) . ? N1 C1 1.352(5) . ? N2 C4 1.372(5) . ? N2 C5 1.400(4) . ? N3 C5 1.343(4) 7 ? N3 C5 1.343(4) . ? N4 C3 1.329(5) . ? N4 C2 1.357(5) . ? N4 Ni1 2.081(3) 4_445 ? N5 C6 1.332(4) 7 ? N5 C6 1.332(4) . ? C1 C2 1.371(5) . ? C3 C4 1.404(5) . ? C5 C6 1.388(5) . ? Cl1 O5 1.396(5) . ? Cl1 O7 1.408(4) . ? Cl1 O8 1.423(4) . ? Cl1 O6 1.425(5) . ? Cl2 O9 1.406(3) . ? Cl2 O12 1.419(4) . ? Cl2 O11 1.425(4) . ? Cl2 O10 1.427(4) . ? 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 N1 91.00(8) . 7 ? O1 Cu1 N1 91.00(8) . . ? N1 Cu1 N1 178.00(16) 7 . ? O1 Cu1 N3 180.0 . . ? N1 Cu1 N3 89.00(8) 7 . ? N1 Cu1 N3 89.00(8) . . ? O1 Cu1 O2 88.77(10) . 7 ? N1 Cu1 O2 90.99(11) 7 7 ? N1 Cu1 O2 89.05(11) . 7 ? N3 Cu1 O2 91.23(10) . 7 ? O1 Cu1 O2 88.77(10) . . ? N1 Cu1 O2 89.05(11) 7 . ? N1 Cu1 O2 90.99(11) . . ? N3 Cu1 O2 91.23(10) . . ? O2 Cu1 O2 177.54(19) 7 . ? O4 Ni1 O4 175.7(2) . 7 ? O4 Ni1 N4 90.45(11) . 3_454 ? O4 Ni1 N4 89.44(12) 7 3_454 ? O4 Ni1 N4 89.44(12) . 6_545 ? O4 Ni1 N4 90.45(11) 7 6_545 ? N4 Ni1 N4 177.30(18) 3_454 6_545 ? O4 Ni1 O3 87.86(11) . . ? O4 Ni1 O3 87.86(11) 7 . ? N4 Ni1 O3 88.65(9) 3_454 . ? N4 Ni1 O3 88.65(9) 6_545 . ? O4 Ni1 N5 92.14(11) . . ? O4 Ni1 N5 92.14(11) 7 . ? N4 Ni1 N5 91.35(9) 3_454 . ? N4 Ni1 N5 91.35(9) 6_545 . ? O3 Ni1 N5 180.0(3) . . ? C4 N1 C1 117.5(3) . . ? C4 N1 Cu1 122.0(2) . . ? C1 N1 Cu1 120.4(2) . . ? C4 N2 C5 125.6(3) . . ? C5 N3 C5 115.9(4) 7 . ? C5 N3 Cu1 122.1(2) 7 . ? C5 N3 Cu1 122.1(2) . . ? C3 N4 C2 117.1(3) . . ? C3 N4 Ni1 121.9(2) . 4_445 ? C2 N4 Ni1 121.0(2) . 4_445 ? C6 N5 C6 116.9(4) 7 . ? C6 N5 Ni1 121.5(2) 7 . ? C6 N5 Ni1 121.5(2) . . ? N1 C1 C2 121.8(3) . . ? N4 C2 C1 121.1(3) . . ? N4 C3 C4 122.1(3) . . ? N1 C4 N2 121.0(3) . . ? N1 C4 C3 120.3(3) . . ? N2 C4 C3 118.7(3) . . ? N3 C5 C6 121.9(3) . . ? N3 C5 N2 120.1(3) . . ? C6 C5 N2 118.0(3) . . ? N5 C6 C5 121.6(3) . . ? O5 Cl1 O7 110.6(4) . . ? O5 Cl1 O8 109.7(3) . . ? O7 Cl1 O8 111.5(3) . . ? O5 Cl1 O6 108.6(5) . . ? O7 Cl1 O6 107.5(3) . . ? O8 Cl1 O6 108.8(3) . . ? O9 Cl2 O12 108.9(3) . . ? O9 Cl2 O11 112.0(3) . . ? O12 Cl2 O11 111.5(3) . . ? O9 Cl2 O10 109.5(3) . . ? O12 Cl2 O10 108.3(3) . . ? O11 Cl2 O10 106.5(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.869 _refine_diff_density_min -0.916 _refine_diff_density_rms 0.083 data_ic10401 _database_code_depnum_ccdc_archive 'CCDC 273187' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 Cl2 Cu N6 O10' _chemical_formula_weight 562.77 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 10.6949(4) _cell_length_b 18.1913(7) _cell_length_c 21.1585(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4116.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5218 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 24.57 _exptl_crystal_description plate _exptl_crystal_colour dark-green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.816 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2280 _exptl_absorpt_coefficient_mu 1.389 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6806 _exptl_absorpt_correction_T_max 0.8187 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART ApexCCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38912 _diffrn_reflns_av_R_equivalents 0.0544 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4722 _reflns_number_gt 4006 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0408P)^2^+4.0766P] 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 4722 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0898 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 Cu Cu 0.02664(3) 0.046677(15) 0.142053(13) 0.01419(9) Uani 1 1 d . . . O1 O 0.02124(17) 0.15437(10) 0.16121(9) 0.0252(4) Uani 1 1 d . . . H1A H 0.0621 0.1742 0.1840 0.038 Uiso 1 1 d . . . H1B H -0.0308 0.1727 0.1516 0.038 Uiso 1 1 d . . . N1 N 0.13681(18) 0.06447(11) 0.06773(9) 0.0178(4) Uani 1 1 d . . . N2 N 0.21753(19) -0.05513(11) 0.07721(10) 0.0208(4) Uani 1 1 d . . . H2B H 0.2889 -0.0788 0.0814 0.025 Uiso 1 1 calc R . . N3 N 0.01345(18) -0.05932(10) 0.11976(9) 0.0149(4) Uani 1 1 d . . . N4 N -0.19210(18) -0.06654(11) 0.16106(9) 0.0166(4) Uani 1 1 d . . . H4B H -0.2660 -0.0804 0.1473 0.020 Uiso 1 1 calc R . . N5 N -0.09170(17) 0.03010(10) 0.21419(9) 0.0149(4) Uani 1 1 d . . . N6 N -0.29575(18) 0.03806(11) 0.29538(9) 0.0177(4) Uani 1 1 d . . . C1 C 0.1475(3) 0.13286(14) 0.04255(12) 0.0247(5) Uani 1 1 d . . . H1C H 0.0812 0.1668 0.0488 0.030 Uiso 1 1 calc R . . C2 C 0.2498(3) 0.15510(16) 0.00845(12) 0.0302(6) Uani 1 1 d . . . H2A H 0.2546 0.2034 -0.0084 0.036 Uiso 1 1 calc R . . C3 C 0.3462(3) 0.10507(17) -0.00089(13) 0.0332(7) Uani 1 1 d . . . H3A H 0.4198 0.1196 -0.0227 0.040 Uiso 1 1 calc R . . C4 C 0.3348(3) 0.03495(16) 0.02142(13) 0.0314(6) Uani 1 1 d . . . H4A H 0.3989 -0.0002 0.0142 0.038 Uiso 1 1 calc R . . C5 C 0.2271(2) 0.01571(13) 0.05516(11) 0.0196(5) Uani 1 1 d . . . C6 C 0.1121(2) -0.09470(13) 0.09382(11) 0.0179(5) Uani 1 1 d . . . C7 C 0.1134(2) -0.17023(14) 0.08366(12) 0.0250(5) Uani 1 1 d . . . H7A H 0.1857 -0.1937 0.0672 0.030 Uiso 1 1 calc R . . C8 C 0.0080(2) -0.21021(14) 0.09802(13) 0.0257(6) Uani 1 1 d . . . H8A H 0.0062 -0.2618 0.0908 0.031 Uiso 1 1 calc R . . C9 C -0.0952(2) -0.17508(14) 0.12288(11) 0.0218(5) Uani 1 1 d . . . H9A H -0.1694 -0.2017 0.1322 0.026 Uiso 1 1 calc R . . C10 C -0.0886(2) -0.10020(13) 0.13400(10) 0.0161(5) Uani 1 1 d . . . C11 C -0.1899(2) -0.01395(12) 0.20704(10) 0.0150(4) Uani 1 1 d . . . C12 C -0.2943(2) -0.00764(13) 0.24748(11) 0.0173(5) Uani 1 1 d . . . H12A H -0.3656 -0.0374 0.2398 0.021 Uiso 1 1 calc R . . C13 C -0.1906(2) 0.07872(13) 0.30572(11) 0.0200(5) Uani 1 1 d . . . H13A H -0.1863 0.1101 0.3415 0.024 Uiso 1 1 calc R . . C14 C -0.0920(2) 0.07488(13) 0.26541(11) 0.0186(5) Uani 1 1 d . . . H14A H -0.0207 0.1046 0.2734 0.022 Uiso 1 1 calc R . . Cl1 Cl -0.25984(6) 0.13242(4) 0.08698(3) 0.02831(16) Uani 1 1 d . . . O2 O -0.17050(17) 0.07543(10) 0.07554(9) 0.0272(4) Uani 1 1 d . A . O3 O -0.33631(19) 0.14522(12) 0.03381(9) 0.0391(5) Uani 1 1 d . A . O4 O -0.1818(3) 0.20210(14) 0.08950(16) 0.0356(7) Uani 0.67 1 d P A 1 O5 O -0.3198(3) 0.1271(2) 0.14460(14) 0.0440(9) Uani 0.67 1 d P A 1 O4' O -0.2269(7) 0.1848(4) 0.1290(3) 0.0416(15) Uiso 0.33 1 d P A 2 O5' O -0.3638(7) 0.0866(4) 0.1239(4) 0.0465(17) Uiso 0.33 1 d P A 2 Cl2 Cl 0.02520(6) 0.36342(3) 0.15898(3) 0.02254(14) Uani 1 1 d . . . O6 O 0.0022(2) 0.43759(12) 0.13880(11) 0.0406(5) Uani 1 1 d . . . O7 O 0.1072(2) 0.36497(11) 0.21236(10) 0.0441(6) Uani 1 1 d . . . O8 O -0.09205(19) 0.33030(12) 0.17617(11) 0.0405(5) Uani 1 1 d . . . O9 O 0.08061(19) 0.32269(12) 0.10856(10) 0.0384(5) Uani 1 1 d . . . O10 O 0.1775(3) 0.21801(13) 0.24037(13) 0.0760(10) Uani 1 1 d . . . H10A H 0.1567 0.2658 0.2388 0.114 Uiso 1 1 d . . . H10B H 0.1870 0.2013 0.2809 0.114 Uiso 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 Cu 0.01279(15) 0.01477(14) 0.01500(14) 0.00033(10) 0.00182(10) -0.00045(11) O1 0.0241(9) 0.0170(8) 0.0343(10) -0.0005(7) -0.0031(8) 0.0006(7) N1 0.0178(10) 0.0220(10) 0.0135(9) 0.0019(8) 0.0002(8) -0.0022(8) N2 0.0127(9) 0.0218(10) 0.0279(11) -0.0015(8) 0.0033(8) 0.0020(8) N3 0.0141(9) 0.0155(9) 0.0150(9) -0.0009(7) 0.0000(7) -0.0007(7) N4 0.0092(9) 0.0208(10) 0.0199(10) -0.0028(8) -0.0005(7) -0.0028(8) N5 0.0114(9) 0.0176(9) 0.0158(9) -0.0004(7) 0.0002(7) -0.0001(7) N6 0.0155(10) 0.0199(10) 0.0178(9) -0.0006(8) 0.0012(8) 0.0008(8) C1 0.0284(14) 0.0246(13) 0.0212(12) 0.0049(10) -0.0028(10) -0.0029(10) C2 0.0381(16) 0.0319(14) 0.0205(12) 0.0032(11) 0.0014(11) -0.0148(12) C3 0.0291(15) 0.0444(17) 0.0261(14) -0.0021(12) 0.0117(11) -0.0166(13) C4 0.0235(14) 0.0378(16) 0.0328(15) -0.0070(12) 0.0114(12) -0.0049(12) C5 0.0184(12) 0.0261(12) 0.0143(11) -0.0031(9) 0.0002(9) -0.0042(10) C6 0.0142(11) 0.0206(11) 0.0190(11) -0.0012(9) 0.0007(9) 0.0011(9) C7 0.0210(13) 0.0219(12) 0.0320(14) -0.0073(10) 0.0043(11) 0.0027(10) C8 0.0262(14) 0.0182(12) 0.0328(14) -0.0045(10) 0.0021(11) -0.0017(10) C9 0.0216(13) 0.0199(12) 0.0240(12) -0.0019(10) 0.0012(10) -0.0045(10) C10 0.0152(11) 0.0186(11) 0.0145(10) 0.0007(8) -0.0013(9) -0.0005(9) C11 0.0144(11) 0.0148(10) 0.0158(10) 0.0030(8) -0.0013(9) 0.0006(8) C12 0.0130(11) 0.0212(11) 0.0178(11) 0.0011(9) -0.0013(9) -0.0013(9) C13 0.0183(12) 0.0231(12) 0.0186(11) -0.0024(9) 0.0000(9) -0.0007(10) C14 0.0159(11) 0.0213(12) 0.0187(11) -0.0012(9) -0.0002(9) -0.0027(9) Cl1 0.0324(4) 0.0303(3) 0.0222(3) -0.0033(2) -0.0053(3) 0.0156(3) O2 0.0283(10) 0.0232(9) 0.0301(10) -0.0057(8) -0.0065(8) 0.0105(8) O3 0.0328(11) 0.0563(14) 0.0281(10) -0.0026(9) -0.0068(9) 0.0221(10) O4 0.0389(18) 0.0149(13) 0.053(2) 0.0015(13) -0.0188(16) 0.0026(12) O5 0.050(2) 0.058(2) 0.0235(15) 0.0033(15) 0.0132(15) 0.0188(18) Cl2 0.0184(3) 0.0241(3) 0.0251(3) -0.0035(2) -0.0011(2) 0.0005(2) O6 0.0446(13) 0.0281(11) 0.0492(14) 0.0061(9) 0.0005(10) 0.0065(9) O7 0.0539(14) 0.0368(12) 0.0415(12) -0.0061(9) -0.0252(11) -0.0014(10) O8 0.0235(11) 0.0362(11) 0.0620(14) 0.0011(10) 0.0092(10) -0.0031(9) O9 0.0334(11) 0.0437(12) 0.0381(11) -0.0158(10) 0.0058(9) 0.0037(10) O10 0.125(3) 0.0323(12) 0.0701(18) -0.0154(12) -0.0629(19) 0.0181(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 Cu N3 1.9901(19) . ? Cu N1 1.9915(19) . ? Cu O1 2.0014(18) . ? Cu N5 2.0057(19) . ? Cu N6 2.3205(19) 6_656 ? Cu O2 2.5884(18) . ? N1 C5 1.338(3) . ? N1 C1 1.358(3) . ? N2 C5 1.374(3) . ? N2 C6 1.384(3) . ? N3 C6 1.352(3) . ? N3 C10 1.354(3) . ? N4 C11 1.365(3) . ? N4 C10 1.389(3) . ? N5 C11 1.330(3) . ? N5 C14 1.356(3) . ? N6 C12 1.311(3) . ? N6 C13 1.363(3) . ? N6 Cu 2.3205(19) 6_556 ? C1 C2 1.371(4) . ? C2 C3 1.390(4) . ? C3 C4 1.366(4) . ? C4 C5 1.400(3) . ? C6 C7 1.391(3) . ? C7 C8 1.376(4) . ? C8 C9 1.379(4) . ? C9 C10 1.384(3) . ? C11 C12 1.411(3) . ? C13 C14 1.358(3) . ? Cl1 O4' 1.350(7) . ? Cl1 O5 1.381(3) . ? Cl1 O3 1.4101(19) . ? Cl1 O2 1.4306(18) . ? Cl1 O4 1.518(3) . ? Cl1 O5' 1.594(8) . ? Cl2 O9 1.428(2) . ? Cl2 O7 1.430(2) . ? Cl2 O6 1.436(2) . ? Cl2 O8 1.438(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 N3 Cu N1 90.70(8) . . ? N3 Cu O1 173.92(8) . . ? N1 Cu O1 91.02(8) . . ? N3 Cu N5 89.42(8) . . ? N1 Cu N5 177.12(8) . . ? O1 Cu N5 88.56(8) . . ? N3 Cu N6 97.34(7) . 6_656 ? N1 Cu N6 88.69(7) . 6_656 ? O1 Cu N6 88.52(7) . 6_656 ? N5 Cu N6 94.15(7) . 6_656 ? N3 Cu O2 90.53(7) . . ? N1 Cu O2 91.13(7) . . ? O1 Cu O2 83.61(6) . . ? N5 Cu O2 85.99(7) . . ? N6 Cu O2 172.13(6) 6_656 . ? C5 N1 C1 117.9(2) . . ? C5 N1 Cu 118.43(16) . . ? C1 N1 Cu 120.58(17) . . ? C5 N2 C6 129.4(2) . . ? C6 N3 C10 117.2(2) . . ? C6 N3 Cu 120.15(16) . . ? C10 N3 Cu 122.44(16) . . ? C11 N4 C10 126.09(19) . . ? C11 N5 C14 116.82(19) . . ? C11 N5 Cu 120.16(15) . . ? C14 N5 Cu 121.30(15) . . ? C12 N6 C13 117.3(2) . . ? C12 N6 Cu 119.58(15) . 6_556 ? C13 N6 Cu 123.15(15) . 6_556 ? N1 C1 C2 123.0(3) . . ? C1 C2 C3 118.3(3) . . ? C4 C3 C2 119.7(2) . . ? C3 C4 C5 118.9(3) . . ? N1 C5 N2 120.0(2) . . ? N1 C5 C4 122.0(2) . . ? N2 C5 C4 118.0(2) . . ? N3 C6 N2 119.4(2) . . ? N3 C6 C7 122.8(2) . . ? N2 C6 C7 117.8(2) . . ? C8 C7 C6 118.7(2) . . ? C7 C8 C9 119.7(2) . . ? C8 C9 C10 118.7(2) . . ? N3 C10 C9 123.0(2) . . ? N3 C10 N4 119.5(2) . . ? C9 C10 N4 117.6(2) . . ? N5 C11 N4 121.2(2) . . ? N5 C11 C12 120.4(2) . . ? N4 C11 C12 118.4(2) . . ? N6 C12 C11 122.0(2) . . ? C14 C13 N6 120.8(2) . . ? N5 C14 C13 122.3(2) . . ? O4' Cl1 O5 65.7(3) . . ? O4' Cl1 O3 124.1(3) . . ? O5 Cl1 O3 116.52(18) . . ? O4' Cl1 O2 116.7(3) . . ? O5 Cl1 O2 114.13(16) . . ? O3 Cl1 O2 111.84(11) . . ? O4' Cl1 O4 40.9(3) . . ? O5 Cl1 O4 106.4(2) . . ? O3 Cl1 O4 102.06(15) . . ? O2 Cl1 O4 104.11(15) . . ? O4' Cl1 O5' 103.1(4) . . ? O5 Cl1 O5' 37.5(3) . . ? O3 Cl1 O5' 94.2(3) . . ? O2 Cl1 O5' 99.8(3) . . ? O4 Cl1 O5' 143.3(3) . . ? Cl1 O2 Cu 126.76(10) . . ? O9 Cl2 O7 110.23(13) . . ? O9 Cl2 O6 109.66(14) . . ? O7 Cl2 O6 108.74(13) . . ? O9 Cl2 O8 109.48(13) . . ? O7 Cl2 O8 110.08(14) . . ? O6 Cl2 O8 108.63(13) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.485 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.077 data_ic10136 _database_code_depnum_ccdc_archive 'CCDC 273188' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H20 Cl2 Cu N6 O11' _chemical_formula_weight 594.81 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 Pna2(1) 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' _cell_length_a 13.6630(2) _cell_length_b 8.2483(1) _cell_length_c 19.8750(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2239.84(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used all _cell_measurement_theta_min 2.05 _cell_measurement_theta_max 27.50 _exptl_crystal_description plate _exptl_crystal_colour pale-green _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.764 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1212 _exptl_absorpt_coefficient_mu 1.285 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.702 _exptl_absorpt_correction_T_max 0.864 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'NONIUS KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15857 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4383 _reflns_number_gt 3743 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0765P)^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 SHELXL _refine_ls_extinction_coef 0.0165(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.075(16) _refine_ls_number_reflns 4383 _refine_ls_number_parameters 347 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1154 _refine_ls_wR_factor_gt 0.0991 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.006 _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 -0.26511(3) 0.74992(5) -0.40146(4) 0.01684(15) Uani 1 1 d . . . O1 O -0.2681(2) 0.9522(4) -0.48462(18) 0.0286(8) Uani 1 1 d . . . H1A H -0.2320 1.0374 -0.4709 0.043 Uiso 1 1 d . . . H1B H -0.2357 0.9053 -0.5189 0.043 Uiso 1 1 d . . . O2 O -0.2577(2) 0.5393(4) -0.31355(16) 0.0255(8) Uani 1 1 d . . . H2A H -0.2337 0.4441 -0.3291 0.038 Uiso 1 1 d . . . H2B H -0.2413 0.5446 -0.2697 0.038 Uiso 1 1 d . . . N1 N -0.2618(3) 0.5699(5) -0.46822(19) 0.0184(9) Uani 1 1 d . . . N2 N -0.1141(2) 0.6667(4) -0.51464(18) 0.0215(8) Uani 1 1 d . . . H2C H -0.0912 0.7026 -0.5532 0.026 Uiso 1 1 calc R . . N3 N -0.1182(2) 0.7533(4) -0.4025(2) 0.0160(5) Uani 1 1 d . . . N4 N -0.1145(2) 0.8398(4) -0.28789(18) 0.0205(8) Uani 1 1 d . . . H4A H -0.0900 0.8048 -0.2496 0.025 Uiso 1 1 calc R . . N5 N -0.2658(2) 0.9292(5) -0.33307(19) 0.0187(8) Uani 1 1 d . . . N6 N 0.08433(19) 0.7566(4) -0.4017(2) 0.0163(6) Uani 1 1 d . . . C1 C -0.3345(3) 0.4554(5) -0.4693(2) 0.0225(10) Uani 1 1 d . . . H1C H -0.3801 0.4541 -0.4333 0.027 Uiso 1 1 calc R . . C2 C -0.3451(3) 0.3431(5) -0.5194(2) 0.0276(10) Uani 1 1 d . . . H2D H -0.3968 0.2661 -0.5183 0.033 Uiso 1 1 calc R . . C3 C -0.2781(4) 0.3449(5) -0.5718(3) 0.0307(11) Uani 1 1 d . . . H3A H -0.2846 0.2706 -0.6081 0.037 Uiso 1 1 calc R . . C4 C -0.2017(3) 0.4550(5) -0.5712(2) 0.0263(10) Uani 1 1 d . . . H4B H -0.1548 0.4570 -0.6064 0.032 Uiso 1 1 calc R . . C5 C -0.1957(3) 0.5634(4) -0.5172(2) 0.0181(8) Uani 1 1 d . . . C6 C -0.0670(3) 0.7167(5) -0.4572(2) 0.0171(9) Uani 1 1 d . . . C7 C 0.0356(4) 0.7231(5) -0.4577(2) 0.0188(9) Uani 1 1 d . . . H7A H 0.0704 0.7035 -0.4983 0.023 Uiso 1 1 calc R . . C8 C 0.0347(3) 0.7896(6) -0.3458(2) 0.0195(9) Uani 1 1 d . . . H8A H 0.0690 0.8108 -0.3051 0.023 Uiso 1 1 calc R . . C9 C -0.0673(3) 0.7932(5) -0.3463(2) 0.0174(9) Uani 1 1 d . . . C10 C -0.1974(3) 0.9374(4) -0.2845(2) 0.0201(9) Uani 1 1 d . . . C11 C -0.2058(3) 1.0446(5) -0.2306(2) 0.0246(10) Uani 1 1 d . . . H11A H -0.1576 1.0469 -0.1962 0.030 Uiso 1 1 calc R . . C12 C -0.2858(4) 1.1478(6) -0.2281(2) 0.0319(11) Uani 1 1 d . . . H12A H -0.2947 1.2189 -0.1910 0.038 Uiso 1 1 calc R . . C13 C -0.3521(3) 1.1457(5) -0.2805(2) 0.0272(10) Uani 1 1 d . . . H13A H -0.4058 1.2189 -0.2810 0.033 Uiso 1 1 calc R . . C14 C -0.3392(3) 1.0362(4) -0.3317(2) 0.0237(10) Uani 1 1 d . . . H14A H -0.3846 1.0365 -0.3679 0.028 Uiso 1 1 calc R . . Cl1 Cl -0.08939(9) 0.43384(12) -0.14763(6) 0.0330(3) Uani 1 1 d . . . O3 O -0.0391(3) 0.5478(5) -0.10492(19) 0.0569(11) Uani 1 1 d . A . O4 O -0.0902(5) 0.4889(7) -0.2144(3) 0.054(2) Uani 0.704(10) 1 d P A 1 O5 O -0.1818(9) 0.4050(16) -0.1206(7) 0.082(4) Uani 0.704(10) 1 d P A 1 O6 O -0.0248(5) 0.3001(8) -0.1412(4) 0.067(2) Uani 0.704(10) 1 d P A 1 O4' O -0.1606(11) 0.5467(14) -0.1824(7) 0.054(5) Uani 0.296(10) 1 d P A 2 O5' O -0.161(2) 0.326(2) -0.1111(14) 0.053(7) Uani 0.296(10) 1 d P A 2 O6' O -0.0543(11) 0.3265(17) -0.1999(9) 0.065(6) Uani 0.296(10) 1 d P A 2 Cl2 Cl -0.58179(7) 0.26884(11) -0.40976(7) 0.0264(3) Uani 1 1 d . . . O7 O -0.5343(3) 0.1207(4) -0.4279(2) 0.0452(10) Uani 1 1 d . . . O8 O -0.6792(2) 0.2386(3) -0.38579(19) 0.0396(10) Uani 1 1 d . . . O9 O -0.5881(3) 0.3736(5) -0.46842(19) 0.0519(10) Uani 1 1 d . . . O10 O -0.5266(2) 0.3517(4) -0.35991(19) 0.0422(9) Uani 1 1 d . . . O11 O 0.0121(3) 0.8391(6) -0.17628(19) 0.0530(11) Uani 1 1 d . . . H11 H 0.0048 0.7567 -0.1520 0.079 Uiso 1 1 calc R . . C15 C 0.0741(5) 0.9478(7) -0.1445(4) 0.072(2) Uani 1 1 d . . . H15A H 0.0659 1.0556 -0.1645 0.109 Uiso 1 1 calc R . . H15B H 0.1420 0.9122 -0.1501 0.109 Uiso 1 1 calc R . . H15C H 0.0581 0.9525 -0.0965 0.109 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0087(2) 0.0197(2) 0.0221(2) -0.00250(16) 0.0000(3) -0.00008(18) O1 0.0205(18) 0.0283(17) 0.037(2) 0.0009(15) -0.0016(14) -0.0041(14) O2 0.0275(19) 0.0240(17) 0.0249(18) 0.0028(14) 0.0007(13) 0.0020(12) N1 0.012(2) 0.0187(19) 0.024(2) -0.0024(18) -0.0011(14) -0.0014(13) N2 0.0149(19) 0.033(2) 0.0165(17) 0.0015(16) -0.0012(15) -0.0064(14) N3 0.0149(14) 0.0167(12) 0.0164(13) 0.0014(11) 0.001(2) 0.0009(12) N4 0.0156(19) 0.0249(17) 0.0211(17) 0.0005(16) -0.0015(15) 0.0015(14) N5 0.0101(19) 0.0224(19) 0.023(2) 0.0022(18) -0.0007(15) -0.0013(14) N6 0.0106(13) 0.0188(13) 0.0193(14) 0.0039(12) 0.000(3) -0.0001(14) C1 0.021(2) 0.022(2) 0.025(2) -0.0001(19) 0.0007(18) 0.0008(17) C2 0.021(2) 0.024(2) 0.038(2) -0.006(2) -0.007(2) -0.0037(18) C3 0.027(3) 0.033(2) 0.033(3) -0.009(2) -0.006(2) 0.0034(19) C4 0.019(2) 0.033(2) 0.027(2) -0.009(2) 0.0002(19) 0.0042(19) C5 0.012(2) 0.0215(18) 0.020(2) -0.0016(18) -0.0019(17) 0.0011(17) C6 0.013(2) 0.0168(17) 0.022(2) 0.0019(18) -0.0019(18) -0.0028(17) C7 0.016(2) 0.021(2) 0.020(2) 0.0015(19) 0.001(2) 0.0027(19) C8 0.014(2) 0.0205(18) 0.025(2) 0.002(2) -0.004(2) 0.002(2) C9 0.015(2) 0.0149(17) 0.022(2) 0.0018(18) -0.0022(18) -0.0012(17) C10 0.015(2) 0.0202(19) 0.025(2) 0.0004(19) 0.0032(18) 0.0014(17) C11 0.020(2) 0.033(2) 0.021(2) -0.0024(19) -0.0038(18) 0.0034(19) C12 0.031(3) 0.033(2) 0.032(3) -0.011(2) 0.004(2) 0.010(2) C13 0.021(2) 0.024(2) 0.036(2) -0.004(2) 0.000(2) 0.0004(17) C14 0.013(2) 0.021(2) 0.037(3) 0.001(2) 0.0014(19) 0.0001(16) Cl1 0.0352(6) 0.0355(6) 0.0282(5) -0.0014(5) 0.0025(6) 0.0071(5) O3 0.041(2) 0.083(3) 0.047(2) 0.000(2) -0.0148(18) -0.0219(19) O4 0.058(4) 0.073(4) 0.031(3) 0.012(3) -0.017(3) -0.002(3) O5 0.040(5) 0.142(10) 0.064(6) -0.051(9) 0.020(4) -0.038(7) O6 0.091(5) 0.045(3) 0.066(5) -0.008(4) -0.019(4) 0.030(3) O4' 0.062(11) 0.047(7) 0.054(9) 0.000(6) -0.037(8) 0.010(6) O5' 0.062(16) 0.061(11) 0.036(9) -0.029(10) 0.017(9) -0.033(11) O6' 0.054(9) 0.055(9) 0.085(14) -0.038(9) 0.040(9) -0.011(7) Cl2 0.0178(5) 0.0230(5) 0.0386(7) -0.0025(5) -0.0015(5) 0.0021(4) O7 0.035(2) 0.0312(17) 0.070(3) -0.0174(18) -0.0103(18) 0.0126(15) O8 0.0248(17) 0.0310(17) 0.063(3) -0.0021(15) 0.0083(17) -0.0052(12) O9 0.041(2) 0.066(2) 0.049(2) 0.0237(19) 0.0098(17) 0.0187(18) O10 0.034(2) 0.0359(19) 0.057(2) -0.0144(17) -0.0103(17) -0.0040(15) O11 0.053(3) 0.063(3) 0.043(2) 0.0090(19) -0.0237(18) -0.0149(19) C15 0.073(5) 0.071(4) 0.073(4) 0.003(4) -0.038(4) -0.023(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.992(4) . ? Cu1 N3 2.007(3) . ? Cu1 N5 2.008(4) . ? Cu1 N6 2.058(3) 3_465 ? Cu1 O1 2.349(4) . ? N1 C5 1.329(6) . ? N1 C1 1.370(5) . ? N2 C6 1.375(6) . ? N2 C5 1.404(5) . ? N3 C6 1.328(6) . ? N3 C9 1.357(6) . ? N4 C9 1.383(6) . ? N4 C10 1.392(5) . ? N5 C14 1.336(5) . ? N5 C10 1.346(6) . ? N6 C7 1.326(6) . ? N6 C8 1.330(6) . ? N6 Cu1 2.058(3) 3_565 ? C1 C2 1.367(6) . ? C2 C3 1.387(7) . ? C3 C4 1.383(7) . ? C4 C5 1.399(6) . ? C6 C7 1.403(7) . ? C8 C9 1.394(7) . ? C10 C11 1.393(6) . ? C11 C12 1.386(6) . ? C12 C13 1.380(7) . ? C13 C14 1.373(6) . ? Cl1 O5 1.393(12) . ? Cl1 O4 1.402(5) . ? Cl1 O6 1.418(6) . ? Cl1 O3 1.441(4) . ? Cl1 O6' 1.447(12) . ? Cl1 O5' 1.51(3) . ? Cl1 O4' 1.514(12) . ? Cl2 O10 1.421(3) . ? Cl2 O7 1.430(3) . ? Cl2 O8 1.436(3) . ? Cl2 O9 1.454(4) . ? O11 C15 1.386(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N3 88.90(15) . . ? N1 Cu1 N5 178.70(15) . . ? N3 Cu1 N5 90.09(15) . . ? N1 Cu1 N6 90.11(14) . 3_465 ? N3 Cu1 N6 179.00(19) . 3_465 ? N5 Cu1 N6 90.90(14) . 3_465 ? N1 Cu1 O1 93.51(17) . . ? N3 Cu1 O1 90.00(14) . . ? N5 Cu1 O1 87.32(12) . . ? N6 Cu1 O1 90.00(14) 3_465 . ? C5 N1 C1 116.9(4) . . ? C5 N1 Cu1 122.2(3) . . ? C1 N1 Cu1 120.5(3) . . ? C6 N2 C5 125.7(4) . . ? C6 N3 C9 117.3(3) . . ? C6 N3 Cu1 122.2(3) . . ? C9 N3 Cu1 120.5(3) . . ? C9 N4 C10 125.6(4) . . ? C14 N5 C10 118.2(4) . . ? C14 N5 Cu1 120.2(3) . . ? C10 N5 Cu1 121.3(3) . . ? C7 N6 C8 119.2(3) . . ? C7 N6 Cu1 119.9(4) . 3_565 ? C8 N6 Cu1 120.9(3) . 3_565 ? C2 C1 N1 123.8(4) . . ? C1 C2 C3 118.0(4) . . ? C4 C3 C2 119.9(4) . . ? C3 C4 C5 118.1(4) . . ? N1 C5 C4 123.2(4) . . ? N1 C5 N2 119.3(3) . . ? C4 C5 N2 117.5(4) . . ? N3 C6 N2 120.1(4) . . ? N3 C6 C7 121.6(4) . . ? N2 C6 C7 118.3(4) . . ? N6 C7 C6 120.2(4) . . ? N6 C8 C9 120.5(4) . . ? N3 C9 N4 121.3(4) . . ? N3 C9 C8 120.9(4) . . ? N4 C9 C8 117.8(4) . . ? N5 C10 N4 120.1(4) . . ? N5 C10 C11 121.8(4) . . ? N4 C10 C11 118.1(4) . . ? C12 C11 C10 118.8(4) . . ? C13 C12 C11 118.9(4) . . ? C14 C13 C12 118.9(4) . . ? N5 C14 C13 123.1(4) . . ? O5 Cl1 O4 114.4(7) . . ? O5 Cl1 O6 113.4(6) . . ? O4 Cl1 O6 109.9(5) . . ? O5 Cl1 O3 108.5(5) . . ? O4 Cl1 O3 110.5(3) . . ? O6 Cl1 O3 99.1(4) . . ? O5 Cl1 O6' 118.2(7) . . ? O4 Cl1 O6' 61.4(8) . . ? O6 Cl1 O6' 51.8(8) . . ? O3 Cl1 O6' 131.6(6) . . ? O5 Cl1 O5' 28.9(9) . . ? O4 Cl1 O5' 129.8(11) . . ? O6 Cl1 O5' 84.5(10) . . ? O3 Cl1 O5' 114.3(10) . . ? O6' Cl1 O5' 101.6(10) . . ? O5 Cl1 O4' 72.5(8) . . ? O4 Cl1 O4' 50.5(6) . . ? O6 Cl1 O4' 156.8(6) . . ? O3 Cl1 O4' 100.1(5) . . ? O6' Cl1 O4' 105.1(10) . . ? O5' Cl1 O4' 99.4(12) . . ? O10 Cl2 O7 110.3(2) . . ? O10 Cl2 O8 110.1(2) . . ? O7 Cl2 O8 110.9(2) . . ? O10 Cl2 O9 107.8(2) . . ? O7 Cl2 O9 109.4(2) . . ? O8 Cl2 O9 108.3(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.092 _refine_diff_density_min -0.697 _refine_diff_density_rms 0.206 data_ic9790 _database_code_depnum_ccdc_archive 'CCDC 273189' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H40 Cl4 Cu2 N16 O22' _chemical_formula_weight 1221.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.2348(1) _cell_length_b 27.2322(4) _cell_length_c 20.5470(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.5252(5) _cell_angle_gamma 90.00 _cell_volume 4593.34(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used all _cell_measurement_theta_min 1.24 _cell_measurement_theta_max 25.00 _exptl_crystal_description plate _exptl_crystal_colour 'pale green' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.767 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2488 _exptl_absorpt_coefficient_mu 1.258 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.865 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'NONIUS KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43197 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8072 _reflns_number_gt 5764 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.1081P)^2^+4.3144P] 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 SHELXL _refine_ls_extinction_coef 0.0032(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8072 _refine_ls_number_parameters 654 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0910 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.1838 _refine_ls_wR_factor_gt 0.1522 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _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 -0.26198(7) -0.01140(2) -0.24217(3) 0.0186(2) Uani 1 1 d . . . Cu2 Cu -0.25073(7) 0.23830(2) -0.26040(3) 0.0199(2) Uani 1 1 d . . . O1 O -0.0442(4) -0.00791(12) -0.16400(16) 0.0262(8) Uani 1 1 d . . . H1 H -0.0595 -0.0088 -0.1166 0.039 Uiso 1 1 d . . . H1' H 0.0370 0.0187 -0.1680 0.039 Uiso 1 1 d . . . O2 O -0.0595(4) 0.23506(12) -0.33877(18) 0.0286(9) Uani 1 1 d . . . H2 H 0.0229 0.2618 -0.3339 0.043 Uiso 1 1 d . . . H2' H -0.0731 0.2338 -0.3876 0.043 Uiso 1 1 d . . . N1 N -0.4370(5) -0.00728(13) -0.1808(2) 0.0200(9) Uani 1 1 d . . . N2 N -0.3383(5) 0.06868(14) -0.13972(19) 0.0217(9) Uani 1 1 d . . . H2B H -0.3010 0.0828 -0.1030 0.026 Uiso 1 1 calc R . . N3 N -0.2624(4) 0.06175(15) -0.24831(18) 0.0177(9) Uani 1 1 d . . . N4 N -0.1864(5) 0.06053(14) -0.35749(19) 0.0217(9) Uani 1 1 d . . . H4A H -0.2138 0.0745 -0.3954 0.026 Uiso 1 1 calc R . . N5 N -0.0974(5) -0.01398(14) -0.30826(19) 0.0195(9) Uani 1 1 d . . . N6 N -0.5174(5) 0.02682(15) -0.0813(2) 0.0263(10) Uani 1 1 d . . . N7 N -0.2651(5) 0.16378(15) -0.25503(19) 0.0192(9) Uani 1 1 d . . . N8 N -0.0404(5) 0.00814(15) -0.4163(2) 0.0253(10) Uani 1 1 d . . . N9 N -0.0670(5) 0.23657(14) -0.1907(2) 0.0206(9) Uani 1 1 d . . . N10 N -0.1403(5) 0.31313(14) -0.1487(2) 0.0238(10) Uani 1 1 d . . . H10B H -0.1602 0.3284 -0.1124 0.029 Uiso 1 1 calc R . . N11 N -0.2391(4) 0.31178(15) -0.26026(18) 0.0174(9) Uani 1 1 d . . . N12 N -0.3413(5) 0.31514(14) -0.37095(19) 0.0230(10) Uani 1 1 d . . . H12B H -0.3083 0.3266 -0.4077 0.028 Uiso 1 1 calc R . . N13 N -0.4407(5) 0.24160(14) -0.3276(2) 0.0216(9) Uani 1 1 d . . . N14 N 0.0067(5) 0.26085(15) -0.0816(2) 0.0281(10) Uani 1 1 d . . . N15 N -0.2285(5) 0.41378(15) -0.25921(19) 0.0192(9) Uani 1 1 d . . . N16 N -0.5481(5) 0.27514(16) -0.4291(2) 0.0294(11) Uani 1 1 d . . . C1 C -0.5529(6) -0.04270(18) -0.1774(3) 0.0243(11) Uani 1 1 d . . . H1A H -0.5661 -0.0667 -0.2110 0.029 Uiso 1 1 calc R . . C2 C -0.6502(6) -0.04444(19) -0.1269(3) 0.0295(13) Uani 1 1 d . . . H2A H -0.7331 -0.0686 -0.1254 0.035 Uiso 1 1 calc R . . C3 C -0.6242(7) -0.00974(18) -0.0777(3) 0.0297(13) Uani 1 1 d . . . H3A H -0.6843 -0.0121 -0.0402 0.036 Uiso 1 1 calc R . . C4 C -0.4333(6) 0.02736(17) -0.1344(2) 0.0205(11) Uani 1 1 d . . . C5 C -0.2965(6) 0.08989(17) -0.1965(2) 0.0185(11) Uani 1 1 d . . . C6 C -0.2943(6) 0.14081(17) -0.1998(2) 0.0213(11) Uani 1 1 d . . . H6A H -0.3139 0.1596 -0.1622 0.026 Uiso 1 1 calc R . . C7 C -0.2333(6) 0.13624(17) -0.3066(3) 0.0231(12) Uani 1 1 d . . . H7A H -0.2129 0.1520 -0.3464 0.028 Uiso 1 1 calc R . . C8 C -0.2295(6) 0.08589(18) -0.3035(2) 0.0206(11) Uani 1 1 d . . . C9 C -0.1065(6) 0.01647(17) -0.3601(2) 0.0195(11) Uani 1 1 d . . . C10 C 0.0543(6) -0.03134(19) -0.4185(3) 0.0289(12) Uani 1 1 d . . . H10A H 0.0984 -0.0394 -0.4585 0.035 Uiso 1 1 calc R . . C11 C 0.0909(6) -0.06124(19) -0.3646(3) 0.0265(12) Uani 1 1 d . . . H11A H 0.1690 -0.0869 -0.3651 0.032 Uiso 1 1 calc R . . C12 C 0.0091(6) -0.05188(17) -0.3109(2) 0.0234(11) Uani 1 1 d . . . H12A H 0.0272 -0.0726 -0.2739 0.028 Uiso 1 1 calc R . . C13 C 0.0332(6) 0.19784(17) -0.1831(3) 0.0232(11) Uani 1 1 d . . . H13A H 0.0438 0.1763 -0.2190 0.028 Uiso 1 1 calc R . . C14 C 0.1211(6) 0.18851(19) -0.1247(3) 0.0283(12) Uani 1 1 d . . . H14A H 0.1945 0.1616 -0.1195 0.034 Uiso 1 1 calc R . . C15 C 0.0971(7) 0.22008(19) -0.0743(3) 0.0316(13) Uani 1 1 d . . . H15A H 0.1470 0.2126 -0.0322 0.038 Uiso 1 1 calc R . . C16 C -0.0641(6) 0.26855(18) -0.1413(2) 0.0231(12) Uani 1 1 d . . . C17 C -0.1897(6) 0.33701(17) -0.2057(2) 0.0192(11) Uani 1 1 d . . . C18 C -0.1864(6) 0.38829(17) -0.2051(2) 0.0222(11) Uani 1 1 d . . . H18A H -0.1538 0.4052 -0.1657 0.027 Uiso 1 1 calc R . . C19 C -0.2742(6) 0.38929(17) -0.3145(2) 0.0212(11) Uani 1 1 d . . . H19A H -0.3004 0.4069 -0.3538 0.025 Uiso 1 1 calc R . . C20 C -0.2832(6) 0.33827(17) -0.3142(2) 0.0194(11) Uani 1 1 d . . . C21 C -0.4472(6) 0.27533(17) -0.3756(2) 0.0218(11) Uani 1 1 d . . . C22 C -0.6623(7) 0.24000(19) -0.4328(3) 0.0341(14) Uani 1 1 d . . . H22A H -0.7359 0.2383 -0.4707 0.041 Uiso 1 1 calc R . . C23 C -0.6770(6) 0.20603(18) -0.3835(3) 0.0274(12) Uani 1 1 d . . . H23A H -0.7631 0.1827 -0.3853 0.033 Uiso 1 1 calc R . . C24 C -0.5611(6) 0.20771(18) -0.3318(3) 0.0241(11) Uani 1 1 d . . . H24A H -0.5654 0.1842 -0.2978 0.029 Uiso 1 1 calc R . . Cl1 Cl 0.27185(16) 0.58309(5) -0.23639(7) 0.0337(4) Uani 1 1 d . . . O3 O 0.2518(6) 0.53403(19) -0.2136(4) 0.092(2) Uani 1 1 d . . . O4 O 0.3916(7) 0.5798(2) -0.2845(3) 0.0767(17) Uani 1 1 d . . . O5 O 0.1299(6) 0.60476(19) -0.2626(3) 0.0796(18) Uani 1 1 d . . . O6 O 0.3532(7) 0.6131(2) -0.1888(3) 0.0884(19) Uani 1 1 d . . . Cl2 Cl -0.19497(19) 0.16440(5) -0.48668(7) 0.0405(4) Uani 1 1 d . . . O7 O -0.0857(6) 0.12948(17) -0.4554(2) 0.0631(15) Uani 1 1 d . . . O8 O -0.3486(5) 0.1617(2) -0.4574(2) 0.0616(14) Uani 1 1 d . . . O9 O -0.1315(8) 0.21305(17) -0.4742(2) 0.0815(19) Uani 1 1 d . . . O10 O -0.2164(6) 0.15687(16) -0.55494(19) 0.0518(12) Uani 1 1 d . . . Cl3 Cl -0.76599(15) 0.32974(5) -0.26662(7) 0.0289(3) Uani 1 1 d . . . O11 O -0.7493(5) 0.28068(16) -0.2399(3) 0.0566(14) Uani 1 1 d . . . O12 O -0.8349(5) 0.36176(15) -0.2217(2) 0.0494(12) Uani 1 1 d . . . O13 O -0.6124(5) 0.34823(16) -0.2818(2) 0.0545(13) Uani 1 1 d . . . O14 O -0.8751(6) 0.32680(18) -0.3241(2) 0.0671(15) Uani 1 1 d . . . Cl4 Cl 0.08206(16) 0.07809(5) 0.00786(6) 0.0283(3) Uani 1 1 d . . . O15 O 0.1815(5) 0.12153(14) 0.01735(19) 0.0417(10) Uani 1 1 d . . . O16 O -0.0679(5) 0.08739(17) 0.0371(2) 0.0540(12) Uani 1 1 d . . . O17 O 0.1620(5) 0.03734(14) 0.04110(19) 0.0419(10) Uani 1 1 d . . . O18 O 0.0553(6) 0.06818(15) -0.06019(18) 0.0505(12) Uani 1 1 d . . . O19 O -0.3116(5) 0.14144(15) -0.04094(19) 0.0415(10) Uani 1 1 d . . . H19 H -0.2228 0.1412 -0.0178 0.062 Uiso 1 1 d . . . C25 C -0.4419(9) 0.1457(3) -0.0001(3) 0.0573(19) Uani 1 1 d . . . H25A H -0.4053 0.1642 0.0393 0.086 Uiso 1 1 calc R . . H25B H -0.4774 0.1129 0.0122 0.086 Uiso 1 1 calc R . . H25C H -0.5329 0.1630 -0.0236 0.086 Uiso 1 1 calc R . . O20 O -0.4534(4) 0.24495(13) -0.17988(18) 0.0314(9) Uani 1 1 d . . . H20 H -0.5408 0.2538 -0.2004 0.047 Uiso 1 1 d . . . C26 C -0.4635(8) 0.2527(2) -0.1119(3) 0.0453(16) Uani 1 1 d . . . H26A H -0.5694 0.2411 -0.0994 0.068 Uiso 1 1 calc R . . H26B H -0.4520 0.2878 -0.1021 0.068 Uiso 1 1 calc R . . H26C H -0.3763 0.2344 -0.0874 0.068 Uiso 1 1 calc R . . O21 O -0.1016(5) 0.37794(16) -0.0449(2) 0.0500(12) Uani 1 1 d . . . H21 H -0.0206 0.3714 -0.0190 0.075 Uiso 1 1 d . . . C27 C -0.2382(10) 0.3880(3) -0.0084(4) 0.076(3) Uani 1 1 d . . . H27A H -0.3040 0.4142 -0.0299 0.114 Uiso 1 1 calc R . . H27B H -0.1999 0.3985 0.0358 0.114 Uiso 1 1 calc R . . H27C H -0.3046 0.3583 -0.0060 0.114 Uiso 1 1 calc R . . O22 O -0.4820(4) -0.01019(13) -0.33505(18) 0.0325(9) Uani 1 1 d . . . H22 H -0.5669 -0.0018 -0.3180 0.049 Uiso 1 1 d . . . C28 C -0.5073(8) -0.0059(3) -0.4041(3) 0.0493(17) Uani 1 1 d . . . H28A H -0.5919 -0.0290 -0.4205 0.074 Uiso 1 1 calc R . . H28B H -0.4056 -0.0133 -0.4239 0.074 Uiso 1 1 calc R . . H28C H -0.5417 0.0277 -0.4156 0.074 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0214(3) 0.0118(3) 0.0232(4) 0.0000(2) 0.0050(3) 0.0000(2) Cu2 0.0230(4) 0.0122(3) 0.0241(4) 0.0003(2) -0.0005(3) -0.0001(2) O1 0.0266(19) 0.026(2) 0.025(2) 0.0021(16) -0.0028(16) -0.0029(16) O2 0.029(2) 0.025(2) 0.033(2) -0.0030(16) 0.0070(17) -0.0030(16) N1 0.021(2) 0.012(2) 0.026(2) 0.0012(18) 0.0007(18) -0.0010(17) N2 0.027(2) 0.021(2) 0.017(2) 0.0000(18) 0.0004(18) -0.0013(19) N3 0.016(2) 0.015(2) 0.022(2) 0.0024(17) 0.0012(17) 0.0005(16) N4 0.032(2) 0.018(2) 0.015(2) 0.0026(17) 0.0024(18) 0.0034(19) N5 0.020(2) 0.016(2) 0.022(2) 0.0007(18) -0.0002(18) 0.0018(17) N6 0.031(2) 0.023(2) 0.026(2) -0.0008(19) 0.009(2) 0.002(2) N7 0.024(2) 0.014(2) 0.020(2) 0.0011(17) 0.0016(18) -0.0006(17) N8 0.028(2) 0.024(2) 0.025(2) 0.0004(19) 0.0055(19) 0.0028(19) N9 0.023(2) 0.015(2) 0.025(2) 0.0022(18) 0.0057(18) -0.0008(18) N10 0.032(2) 0.020(2) 0.020(2) 0.0005(18) 0.0031(19) 0.0044(19) N11 0.019(2) 0.013(2) 0.021(2) 0.0015(17) 0.0027(17) 0.0008(16) N12 0.031(2) 0.021(2) 0.017(2) -0.0011(18) 0.0023(18) -0.0029(19) N13 0.025(2) 0.014(2) 0.026(2) -0.0021(18) 0.0017(19) 0.0011(18) N14 0.035(3) 0.023(2) 0.026(3) 0.0036(19) -0.001(2) 0.000(2) N15 0.021(2) 0.015(2) 0.022(2) 0.0002(18) 0.0035(18) -0.0005(17) N16 0.034(3) 0.026(2) 0.026(3) 0.000(2) -0.006(2) -0.004(2) C1 0.023(3) 0.019(3) 0.031(3) -0.001(2) 0.002(2) -0.004(2) C2 0.025(3) 0.026(3) 0.038(3) 0.003(3) 0.010(3) -0.001(2) C3 0.031(3) 0.026(3) 0.033(3) 0.005(3) 0.012(2) -0.001(2) C4 0.021(3) 0.017(3) 0.024(3) 0.001(2) -0.001(2) -0.001(2) C5 0.018(2) 0.016(2) 0.022(3) -0.001(2) -0.001(2) 0.000(2) C6 0.020(3) 0.020(3) 0.024(3) -0.007(2) 0.003(2) -0.001(2) C7 0.029(3) 0.017(3) 0.023(3) 0.004(2) 0.002(2) 0.000(2) C8 0.016(2) 0.023(3) 0.023(3) 0.001(2) -0.001(2) 0.000(2) C9 0.018(2) 0.018(3) 0.022(3) -0.003(2) -0.001(2) -0.002(2) C10 0.033(3) 0.027(3) 0.028(3) -0.006(2) 0.011(2) -0.003(2) C11 0.023(3) 0.025(3) 0.032(3) 0.000(2) 0.006(2) 0.007(2) C12 0.026(3) 0.015(3) 0.029(3) 0.002(2) -0.001(2) 0.001(2) C13 0.022(3) 0.017(3) 0.031(3) -0.001(2) 0.004(2) -0.002(2) C14 0.026(3) 0.021(3) 0.036(3) 0.004(2) -0.004(2) 0.003(2) C15 0.034(3) 0.029(3) 0.031(3) 0.007(3) -0.004(2) 0.001(3) C16 0.022(3) 0.022(3) 0.026(3) 0.006(2) 0.005(2) -0.003(2) C17 0.019(2) 0.017(3) 0.022(3) 0.000(2) 0.005(2) 0.000(2) C18 0.024(3) 0.019(3) 0.024(3) -0.001(2) 0.000(2) 0.001(2) C19 0.026(3) 0.016(3) 0.022(3) 0.003(2) 0.001(2) 0.000(2) C20 0.020(3) 0.016(3) 0.022(3) -0.002(2) 0.005(2) -0.002(2) C21 0.026(3) 0.018(3) 0.022(3) -0.001(2) 0.005(2) 0.002(2) C22 0.034(3) 0.029(3) 0.037(3) -0.008(3) -0.011(3) -0.001(3) C23 0.025(3) 0.020(3) 0.036(3) -0.002(2) 0.000(2) -0.002(2) C24 0.023(3) 0.020(3) 0.030(3) 0.000(2) 0.005(2) 0.000(2) Cl1 0.0324(8) 0.0269(8) 0.0418(8) 0.0001(6) 0.0029(6) -0.0020(6) O3 0.048(3) 0.052(3) 0.180(6) 0.037(4) 0.025(4) 0.005(3) O4 0.083(4) 0.075(4) 0.076(4) 0.013(3) 0.037(3) 0.022(3) O5 0.044(3) 0.067(3) 0.122(5) -0.022(3) -0.037(3) 0.023(3) O6 0.068(4) 0.080(4) 0.109(5) -0.041(4) -0.040(3) 0.008(3) Cl2 0.0517(9) 0.0393(9) 0.0309(8) 0.0057(7) 0.0059(7) 0.0097(7) O7 0.053(3) 0.070(3) 0.070(3) 0.038(3) 0.027(3) 0.033(3) O8 0.038(3) 0.115(4) 0.032(2) 0.002(3) 0.005(2) 0.018(3) O9 0.157(6) 0.040(3) 0.046(3) -0.002(2) -0.009(3) -0.022(3) O10 0.081(3) 0.049(3) 0.027(2) -0.004(2) 0.014(2) 0.009(2) Cl3 0.0242(7) 0.0226(7) 0.0400(8) -0.0014(6) 0.0041(6) -0.0018(5) O11 0.036(3) 0.029(2) 0.105(4) 0.021(2) 0.009(3) 0.0026(18) O12 0.042(3) 0.049(3) 0.059(3) -0.010(2) 0.010(2) 0.009(2) O13 0.039(3) 0.041(3) 0.086(4) -0.015(2) 0.023(2) -0.012(2) O14 0.075(4) 0.069(3) 0.053(3) 0.007(3) -0.022(3) -0.026(3) Cl4 0.0336(7) 0.0264(7) 0.0251(7) 0.0004(6) 0.0038(6) 0.0000(6) O15 0.058(3) 0.030(2) 0.037(2) -0.0072(18) 0.005(2) -0.013(2) O16 0.034(2) 0.069(3) 0.061(3) 0.021(2) 0.017(2) 0.015(2) O17 0.057(3) 0.032(2) 0.038(2) 0.0084(19) 0.012(2) 0.015(2) O18 0.078(3) 0.048(3) 0.024(2) -0.0005(19) -0.004(2) -0.017(2) O19 0.036(2) 0.052(3) 0.036(2) -0.0085(19) -0.0021(19) 0.002(2) C25 0.055(4) 0.062(5) 0.058(5) 0.014(4) 0.022(4) 0.017(4) O20 0.029(2) 0.033(2) 0.033(2) 0.0016(17) 0.0044(17) 0.0059(17) C26 0.044(4) 0.055(4) 0.039(4) -0.001(3) 0.015(3) -0.003(3) O21 0.055(3) 0.052(3) 0.042(3) -0.011(2) 0.000(2) 0.005(2) C27 0.073(6) 0.099(7) 0.059(5) 0.033(5) 0.025(4) 0.030(5) O22 0.027(2) 0.034(2) 0.036(2) -0.0035(18) 0.0005(17) 0.0075(17) C28 0.044(4) 0.064(4) 0.039(4) -0.005(3) -0.003(3) 0.000(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.992(4) . ? Cu1 N5 1.994(4) . ? Cu1 N3 1.996(4) . ? Cu1 N15 2.039(4) 2_444 ? Cu1 O1 2.313(3) . ? Cu1 O22 2.526(4) . ? Cu2 N9 2.000(4) . ? Cu2 N11 2.003(4) . ? Cu2 N13 2.005(4) . ? Cu2 N7 2.036(4) . ? Cu2 O2 2.341(3) . ? Cu2 O20 2.447(4) . ? N1 C4 1.340(6) . ? N1 C1 1.363(6) . ? N2 C5 1.369(6) . ? N2 C4 1.380(6) . ? N3 C8 1.357(6) . ? N3 C5 1.360(6) . ? N4 C9 1.372(6) . ? N4 C8 1.376(6) . ? N5 C9 1.348(6) . ? N5 C12 1.358(6) . ? N6 C3 1.335(7) . ? N6 C4 1.337(6) . ? N7 C6 1.334(6) . ? N7 C7 1.341(6) . ? N8 C10 1.331(7) . ? N8 C9 1.333(6) . ? N9 C16 1.337(6) . ? N9 C13 1.341(6) . ? N10 C16 1.370(6) . ? N10 C17 1.374(6) . ? N11 C20 1.348(6) . ? N11 C17 1.349(6) . ? N12 C20 1.377(6) . ? N12 C21 1.390(6) . ? N13 C21 1.345(6) . ? N13 C24 1.352(6) . ? N14 C16 1.332(7) . ? N14 C15 1.338(7) . ? N15 C18 1.333(6) . ? N15 C19 1.345(6) . ? N15 Cu1 2.039(4) 2_454 ? N16 C21 1.325(6) . ? N16 C22 1.339(7) . ? C1 C2 1.360(7) . ? C2 C3 1.389(7) . ? C5 C6 1.388(7) . ? C7 C8 1.373(7) . ? C10 C11 1.389(7) . ? C11 C12 1.361(7) . ? C13 C14 1.377(7) . ? C14 C15 1.372(8) . ? C17 C18 1.397(7) . ? C19 C20 1.391(7) . ? C22 C23 1.384(8) . ? C23 C24 1.371(7) . ? Cl1 O5 1.380(5) . ? Cl1 O6 1.403(5) . ? Cl1 O3 1.430(5) . ? Cl1 O4 1.453(5) . ? Cl2 O10 1.415(4) . ? Cl2 O7 1.427(4) . ? Cl2 O9 1.440(5) . ? Cl2 O8 1.445(5) . ? Cl3 O13 1.419(4) . ? Cl3 O12 1.420(4) . ? Cl3 O14 1.428(5) . ? Cl3 O11 1.447(4) . ? Cl4 O18 1.424(4) . ? Cl4 O17 1.436(4) . ? Cl4 O16 1.438(4) . ? Cl4 O15 1.443(4) . ? O19 C25 1.418(7) . ? O20 C26 1.421(7) . ? O21 C27 1.427(8) . ? O22 C28 1.423(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N5 176.22(16) . . ? N1 Cu1 N3 89.20(15) . . ? N5 Cu1 N3 89.43(15) . . ? N1 Cu1 N15 90.96(15) . 2_444 ? N5 Cu1 N15 90.20(15) . 2_444 ? N3 Cu1 N15 176.49(15) . 2_444 ? N1 Cu1 O1 96.79(14) . . ? N5 Cu1 O1 86.73(14) . . ? N3 Cu1 O1 90.02(13) . . ? N15 Cu1 O1 93.45(14) 2_444 . ? N1 Cu1 O22 88.04(14) . . ? N5 Cu1 O22 88.36(14) . . ? N3 Cu1 O22 86.65(13) . . ? N15 Cu1 O22 89.85(14) 2_444 . ? O1 Cu1 O22 174.09(12) . . ? N9 Cu2 N11 89.37(15) . . ? N9 Cu2 N13 177.51(16) . . ? N11 Cu2 N13 89.47(15) . . ? N9 Cu2 N7 88.95(15) . . ? N11 Cu2 N7 176.72(16) . . ? N13 Cu2 N7 92.09(15) . . ? N9 Cu2 O2 88.86(15) . . ? N11 Cu2 O2 90.22(13) . . ? N13 Cu2 O2 93.35(15) . . ? N7 Cu2 O2 92.57(14) . . ? N9 Cu2 O20 92.01(14) . . ? N11 Cu2 O20 87.72(14) . . ? N13 Cu2 O20 85.74(15) . . ? N7 Cu2 O20 89.51(14) . . ? O2 Cu2 O20 177.75(12) . . ? C4 N1 C1 116.0(4) . . ? C4 N1 Cu1 120.9(3) . . ? C1 N1 Cu1 122.5(3) . . ? C5 N2 C4 126.4(4) . . ? C8 N3 C5 116.7(4) . . ? C8 N3 Cu1 122.5(3) . . ? C5 N3 Cu1 120.8(3) . . ? C9 N4 C8 128.8(4) . . ? C9 N5 C12 115.6(4) . . ? C9 N5 Cu1 121.2(3) . . ? C12 N5 Cu1 122.0(3) . . ? C3 N6 C4 116.1(4) . . ? C6 N7 C7 118.0(4) . . ? C6 N7 Cu2 121.9(3) . . ? C7 N7 Cu2 119.9(3) . . ? C10 N8 C9 116.6(4) . . ? C16 N9 C13 116.8(4) . . ? C16 N9 Cu2 119.8(3) . . ? C13 N9 Cu2 121.7(3) . . ? C16 N10 C17 128.1(4) . . ? C20 N11 C17 117.0(4) . . ? C20 N11 Cu2 121.6(3) . . ? C17 N11 Cu2 121.4(3) . . ? C20 N12 C21 126.0(4) . . ? C21 N13 C24 115.6(4) . . ? C21 N13 Cu2 121.3(3) . . ? C24 N13 Cu2 122.8(3) . . ? C16 N14 C15 115.6(4) . . ? C18 N15 C19 118.9(4) . . ? C18 N15 Cu1 121.1(3) . 2_454 ? C19 N15 Cu1 119.9(3) . 2_454 ? C21 N16 C22 116.2(5) . . ? C2 C1 N1 121.4(5) . . ? C1 C2 C3 117.8(5) . . ? N6 C3 C2 122.0(5) . . ? N6 C4 N1 126.1(4) . . ? N6 C4 N2 114.0(4) . . ? N1 C4 N2 120.0(4) . . ? N3 C5 N2 120.7(4) . . ? N3 C5 C6 121.3(4) . . ? N2 C5 C6 117.9(4) . . ? N7 C6 C5 120.9(4) . . ? N7 C7 C8 121.8(5) . . ? N3 C8 C7 121.1(4) . . ? N3 C8 N4 120.8(4) . . ? C7 C8 N4 118.1(4) . . ? N8 C9 N5 125.4(4) . . ? N8 C9 N4 114.4(4) . . ? N5 C9 N4 120.2(4) . . ? N8 C10 C11 122.5(5) . . ? C12 C11 C10 116.5(5) . . ? N5 C12 C11 122.5(5) . . ? N9 C13 C14 121.5(5) . . ? C15 C14 C13 116.5(5) . . ? N14 C15 C14 123.2(5) . . ? N14 C16 N9 125.3(5) . . ? N14 C16 N10 113.9(4) . . ? N9 C16 N10 120.8(5) . . ? N11 C17 N10 121.1(4) . . ? N11 C17 C18 121.4(4) . . ? N10 C17 C18 117.4(4) . . ? N15 C18 C17 120.6(4) . . ? N15 C19 C20 120.3(4) . . ? N11 C20 N12 120.3(4) . . ? N11 C20 C19 121.8(4) . . ? N12 C20 C19 118.0(4) . . ? N16 C21 N13 126.3(5) . . ? N16 C21 N12 114.1(4) . . ? N13 C21 N12 119.6(4) . . ? N16 C22 C23 122.5(5) . . ? C24 C23 C22 116.6(5) . . ? N13 C24 C23 122.3(5) . . ? O5 Cl1 O6 111.5(3) . . ? O5 Cl1 O3 114.3(3) . . ? O6 Cl1 O3 112.2(4) . . ? O5 Cl1 O4 111.1(4) . . ? O6 Cl1 O4 101.4(4) . . ? O3 Cl1 O4 105.5(3) . . ? O10 Cl2 O7 112.0(3) . . ? O10 Cl2 O9 109.0(3) . . ? O7 Cl2 O9 109.0(3) . . ? O10 Cl2 O8 111.1(3) . . ? O7 Cl2 O8 108.6(3) . . ? O9 Cl2 O8 106.9(4) . . ? O13 Cl3 O12 109.5(3) . . ? O13 Cl3 O14 110.6(3) . . ? O12 Cl3 O14 108.3(3) . . ? O13 Cl3 O11 110.6(3) . . ? O12 Cl3 O11 110.5(3) . . ? O14 Cl3 O11 107.3(3) . . ? O18 Cl4 O17 110.5(3) . . ? O18 Cl4 O16 111.9(3) . . ? O17 Cl4 O16 108.3(2) . . ? O18 Cl4 O15 109.3(2) . . ? O17 Cl4 O15 109.6(3) . . ? O16 Cl4 O15 107.2(3) . . ? C26 O20 Cu2 140.5(3) . . ? C28 O22 Cu1 142.6(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.314 _refine_diff_density_min -0.862 _refine_diff_density_rms 0.251