# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Goutam Lahiri' _publ_contact_author_email LAHIRI@CHEM.IITB.AC.IN _publ_section_title ; Single-crystal to single-crystal transformations in discrete hydrated dimeric copper complexes ; loop_ _publ_author_name 'Goutam Lahiri' 'Pradeep Mathur' 'Shaikh M Mobin' 'Ashwini Srivastava' # Attachment 'ALL-REVISEDR3.cif' data_1a _database_code_depnum_ccdc_archive 'CCDC 652141' #TrackingRef 'ALL-REVISEDR3.cif'.2H2O #TrackingRef 'ALL-REVISEDR3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H11 CU N1 2H2O' _chemical_formula_sum 'C9 H15 Cu N O5' _chemical_formula_weight 280.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3200 1.2650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.842(2) _cell_length_b 8.568(2) _cell_length_c 9.994(3) _cell_angle_alpha 71.58(2) _cell_angle_beta 78.30(3) _cell_angle_gamma 69.45(3) _cell_volume 593.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5980 _cell_measurement_theta_min 3.1753 _cell_measurement_theta_max 32.4048 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.571 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 290 _exptl_absorpt_coefficient_mu 1.845 _exptl_absorpt_correction_T_min 0.5407 _exptl_absorpt_correction_T_max 0.5897 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6111 _diffrn_reflns_av_R_equivalents 0.0180 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2079 _reflns_number_gt 1874 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+0.4045P] 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 2079 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0271 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_ref 0.0692 _refine_ls_wR_factor_gt 0.0681 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.003 _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 0.32004(4) 0.55346(4) 0.08829(3) 0.01707(11) Uani 1 1 d . . . O1 O 0.4381(2) 0.6110(2) -0.09862(16) 0.0208(4) Uani 1 1 d . . . O2 O 0.2373(2) 0.4844(2) 0.29013(15) 0.0195(4) Uani 1 1 d . . . O3 O 0.3605(3) 0.6850(2) 0.27349(18) 0.0293(4) Uani 1 1 d . . . N1 N 0.0699(3) 0.6936(3) 0.0333(2) 0.0189(4) Uani 1 1 d . . . C1 C -0.0723(3) 0.6404(3) 0.1076(3) 0.0229(5) Uani 1 1 d . . . H1 H -0.0517 0.5509 0.1934 0.027 Uiso 1 1 calc R . . C2 C -0.2463(3) 0.7092(4) 0.0654(3) 0.0277(6) Uani 1 1 d . . . H2 H -0.3437 0.6690 0.1210 0.033 Uiso 1 1 calc R . . C3 C -0.2754(4) 0.8380(4) -0.0595(3) 0.0314(6) Uani 1 1 d . . . H3 H -0.3930 0.8868 -0.0927 0.038 Uiso 1 1 calc R . . C4 C -0.1310(4) 0.8952(4) -0.1357(3) 0.0289(6) Uani 1 1 d . . . H4 H -0.1495 0.9844 -0.2217 0.035 Uiso 1 1 calc R . . C5 C 0.0408(3) 0.8231(3) -0.0874(2) 0.0213(5) Uani 1 1 d . . . C6 C 0.2004(3) 0.8821(3) -0.1674(3) 0.0251(5) Uani 1 1 d . . . H6B H 0.2465 0.9262 -0.1061 0.030 Uiso 1 1 calc R . . H6A H 0.1588 0.9788 -0.2514 0.030 Uiso 1 1 calc R . . C7 C 0.3558(3) 0.7390(3) -0.2155(2) 0.0229(5) Uani 1 1 d . . . H7A H 0.3079 0.6862 -0.2686 0.027 Uiso 1 1 calc R . . H7B H 0.4487 0.7885 -0.2800 0.027 Uiso 1 1 calc R . . C8 C 0.2802(3) 0.5794(3) 0.3456(2) 0.0204(5) Uani 1 1 d . . . C9 C 0.2289(4) 0.5600(4) 0.5020(3) 0.0321(6) Uani 1 1 d . . . H9A H 0.3398 0.5237 0.5492 0.048 Uiso 1 1 calc R . . H9B H 0.1652 0.4726 0.5411 0.048 Uiso 1 1 calc R . . H9C H 0.1481 0.6710 0.5176 0.048 Uiso 1 1 calc R . . O111 O 0.5289(4) 0.0927(3) 0.6397(3) 0.0487(7) Uani 1 1 d . . . O222 O 0.7656(4) 0.8396(4) 0.5124(3) 0.0396(6) Uani 1 1 d . . . H111 H 0.544(5) 0.174(6) 0.653(4) 0.058(12) Uiso 1 1 d . . . H444 H 0.773(5) 0.743(5) 0.576(4) 0.044(10) Uiso 1 1 d . . . H222 H 0.463(5) 0.121(5) 0.612(4) 0.041(14) Uiso 1 1 d . . . H333 H 0.719(6) 0.887(5) 0.547(4) 0.037(15) 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 0.01571(16) 0.02174(17) 0.01345(16) -0.00349(11) -0.00095(10) -0.00681(12) O1 0.0173(8) 0.0248(9) 0.0138(7) -0.0001(7) -0.0007(6) -0.0038(7) O2 0.0201(8) 0.0243(9) 0.0143(7) -0.0050(7) -0.0004(6) -0.0081(7) O3 0.0334(10) 0.0313(10) 0.0286(9) -0.0107(8) 0.0012(8) -0.0163(9) N1 0.0181(10) 0.0220(10) 0.0184(9) -0.0078(8) -0.0004(7) -0.0072(9) C1 0.0206(12) 0.0277(13) 0.0225(12) -0.0086(10) 0.0001(9) -0.0098(11) C2 0.0191(13) 0.0364(15) 0.0349(14) -0.0181(12) 0.0036(10) -0.0132(12) C3 0.0193(13) 0.0365(16) 0.0391(15) -0.0131(12) -0.0085(11) -0.0038(12) C4 0.0266(14) 0.0290(14) 0.0274(13) -0.0046(11) -0.0079(10) -0.0040(12) C5 0.0206(12) 0.0206(12) 0.0226(12) -0.0078(10) -0.0024(9) -0.0045(10) C6 0.0237(13) 0.0215(13) 0.0251(12) 0.0011(10) -0.0021(10) -0.0079(11) C7 0.0226(13) 0.0266(13) 0.0146(11) 0.0012(10) -0.0046(9) -0.0063(11) C8 0.0154(11) 0.0235(13) 0.0199(11) -0.0061(10) -0.0037(9) -0.0017(10) C9 0.0323(15) 0.0455(17) 0.0220(13) -0.0155(12) -0.0003(11) -0.0120(13) O111 0.0588(18) 0.0349(14) 0.0632(17) -0.0136(11) -0.0334(14) -0.0122(13) O222 0.0439(15) 0.0335(14) 0.0389(13) 0.0000(13) -0.0077(11) -0.0155(12) _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 1.9045(16) . ? Cu1 O1 1.9245(18) 2_665 ? Cu1 O2 1.9557(16) . ? Cu1 N1 1.990(2) . ? Cu1 Cu1 3.0178(12) 2_665 ? O1 C7 1.409(3) . ? O1 Cu1 1.9245(18) 2_665 ? O2 C8 1.279(3) . ? O3 C8 1.241(3) . ? N1 C1 1.345(3) . ? N1 C5 1.351(3) . ? C1 C2 1.378(3) . ? C1 H1 0.9500 . ? C2 C3 1.377(4) . ? C2 H2 0.9500 . ? C3 C4 1.381(4) . ? C3 H3 0.9500 . ? C4 C5 1.386(3) . ? C4 H4 0.9500 . ? C5 C6 1.498(3) . ? C6 C7 1.518(4) . ? C6 H6B 0.9900 . ? C6 H6A 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.503(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? O111 H111 0.80(4) . ? O111 H222 0.57(4) . ? O222 H444 0.86(4) . ? O222 H333 0.59(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 O1 75.98(8) . 2_665 ? O1 Cu1 O2 170.87(6) . . ? O1 Cu1 O2 96.35(7) 2_665 . ? O1 Cu1 N1 94.56(8) . . ? O1 Cu1 N1 163.30(7) 2_665 . ? O2 Cu1 N1 94.05(8) . . ? O1 Cu1 Cu1 38.22(5) . 2_665 ? O1 Cu1 Cu1 37.76(5) 2_665 2_665 ? O2 Cu1 Cu1 133.92(5) . 2_665 ? N1 Cu1 Cu1 131.38(6) . 2_665 ? C7 O1 Cu1 125.72(14) . . ? C7 O1 Cu1 130.15(14) . 2_665 ? Cu1 O1 Cu1 104.02(8) . 2_665 ? C8 O2 Cu1 104.90(14) . . ? C1 N1 C5 118.7(2) . . ? C1 N1 Cu1 118.22(16) . . ? C5 N1 Cu1 122.30(16) . . ? N1 C1 C2 123.2(2) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C3 C2 C1 118.2(2) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C2 C3 C4 119.0(2) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C3 C4 C5 120.4(2) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? N1 C5 C4 120.4(2) . . ? N1 C5 C6 117.8(2) . . ? C4 C5 C6 121.8(2) . . ? C5 C6 C7 112.8(2) . . ? C5 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? H6B C6 H6A 107.8 . . ? O1 C7 C6 110.88(19) . . ? O1 C7 H7A 109.5 . . ? C6 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? O3 C8 O2 121.6(2) . . ? O3 C8 C9 120.7(2) . . ? O2 C8 C9 117.8(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? H111 O111 H222 104(5) . . ? H444 O222 H333 98(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 O1 C7 176.4(2) 2_665 . . . ? O2 Cu1 O1 C7 -150.2(4) . . . . ? N1 Cu1 O1 C7 10.38(19) . . . . ? Cu1 Cu1 O1 C7 176.4(2) 2_665 . . . ? O1 Cu1 O1 Cu1 0.0 2_665 . . 2_665 ? O2 Cu1 O1 Cu1 33.4(5) . . . 2_665 ? N1 Cu1 O1 Cu1 -166.03(8) . . . 2_665 ? O1 Cu1 O2 C8 57.6(5) . . . . ? O1 Cu1 O2 C8 90.14(15) 2_665 . . . ? N1 Cu1 O2 C8 -102.95(15) . . . . ? Cu1 Cu1 O2 C8 85.85(15) 2_665 . . . ? O1 Cu1 N1 C1 149.69(17) . . . . ? O1 Cu1 N1 C1 95.1(3) 2_665 . . . ? O2 Cu1 N1 C1 -33.34(18) . . . . ? Cu1 Cu1 N1 C1 138.21(15) 2_665 . . . ? O1 Cu1 N1 C5 -20.13(19) . . . . ? O1 Cu1 N1 C5 -74.7(3) 2_665 . . . ? O2 Cu1 N1 C5 156.84(18) . . . . ? Cu1 Cu1 N1 C5 -31.6(2) 2_665 . . . ? C5 N1 C1 C2 1.3(4) . . . . ? Cu1 N1 C1 C2 -168.87(19) . . . . ? N1 C1 C2 C3 0.5(4) . . . . ? C1 C2 C3 C4 -1.3(4) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C1 N1 C5 C4 -2.2(3) . . . . ? Cu1 N1 C5 C4 167.53(18) . . . . ? C1 N1 C5 C6 179.1(2) . . . . ? Cu1 N1 C5 C6 -11.1(3) . . . . ? C3 C4 C5 N1 1.4(4) . . . . ? C3 C4 C5 C6 -180.0(2) . . . . ? N1 C5 C6 C7 60.1(3) . . . . ? C4 C5 C6 C7 -118.5(3) . . . . ? Cu1 O1 C7 C6 28.1(3) . . . . ? Cu1 O1 C7 C6 -156.41(16) 2_665 . . . ? C5 C6 C7 O1 -67.9(3) . . . . ? Cu1 O2 C8 O3 -1.2(3) . . . . ? Cu1 O2 C8 C9 178.31(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O111 H111 O3 0.80(4) 1.99(4) 2.764(3) 161(4) 2_666 C4 H4 O3 0.95 2.68 3.377(3) 131.1 2_575 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.712 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.065 #===END data_1b _database_code_depnum_ccdc_archive 'CCDC 737391' #TrackingRef 'ALL-REVISEDR3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 Cu2 N2 O6' _chemical_formula_weight 489.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.702(3) _cell_length_b 7.894(3) _cell_length_c 8.698(4) _cell_angle_alpha 100.46(4) _cell_angle_beta 106.16(4) _cell_angle_gamma 93.14(4) _cell_volume 496.3(4) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1604 _cell_measurement_theta_min 3.1201 _cell_measurement_theta_max 32.4303 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.638 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 250 _exptl_absorpt_coefficient_mu 2.179 _exptl_absorpt_correction_T_min 0.4915 _exptl_absorpt_correction_T_max 0.5423 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4327 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1748 _reflns_number_gt 1475 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0448P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1748 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0749 _refine_ls_wR_factor_gt 0.0724 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.13428(5) 0.15888(4) 0.58243(4) 0.03778(15) Uani 1 1 d . . . O1 O 0.0117(3) 0.0215(2) 0.3727(2) 0.0443(5) Uani 1 1 d . . . O2 O 0.2623(3) 0.2647(2) 0.8102(2) 0.0460(5) Uani 1 1 d . . . O3 O 0.4370(3) 0.0813(3) 0.7288(3) 0.0572(6) Uani 1 1 d . . . N1 N 0.2096(3) 0.3591(3) 0.4945(3) 0.0397(6) Uani 1 1 d . . . C1 C 0.2311(4) 0.5203(3) 0.5866(4) 0.0477(8) Uani 1 1 d . . . H1 H 0.2212 0.5328 0.6944 0.057 Uiso 1 1 calc R . . C2 C 0.2668(4) 0.6680(4) 0.5309(5) 0.0583(10) Uani 1 1 d . . . H2 H 0.2837 0.7791 0.6003 0.070 Uiso 1 1 calc R . . C3 C 0.2772(5) 0.6522(4) 0.3767(6) 0.0698(11) Uani 1 1 d . . . H3 H 0.3006 0.7518 0.3354 0.084 Uiso 1 1 calc R . . C4 C 0.2532(5) 0.4877(4) 0.2799(5) 0.0651(10) Uani 1 1 d . . . H4 H 0.2580 0.4742 0.1705 0.078 Uiso 1 1 calc R . . C5 C 0.2221(4) 0.3421(4) 0.3418(4) 0.0467(8) Uani 1 1 d . . . C6 C 0.2030(5) 0.1605(4) 0.2443(4) 0.0530(8) Uani 1 1 d . . . H6A H 0.3047 0.1003 0.2988 0.064 Uiso 1 1 calc R . . H6B H 0.2141 0.1665 0.1347 0.064 Uiso 1 1 calc R . . C7 C 0.0250(5) 0.0535(4) 0.2234(4) 0.0488(8) Uani 1 1 d . . . H7A H -0.0779 0.1160 0.1751 0.059 Uiso 1 1 calc R . . H7B H 0.0165 -0.0582 0.1470 0.059 Uiso 1 1 calc R . . C8 C 0.4084(4) 0.1925(3) 0.8339(4) 0.0387(7) Uani 1 1 d . . . C9 C 0.5460(5) 0.2498(4) 0.9987(4) 0.0583(9) Uani 1 1 d . . . H9A H 0.5118 0.1899 1.0771 0.087 Uiso 1 1 calc R . . H9B H 0.5500 0.3752 1.0355 0.087 Uiso 1 1 calc R . . H9C H 0.6661 0.2216 0.9912 0.087 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 0.0383(2) 0.0313(2) 0.0342(2) 0.00254(13) -0.00068(15) -0.00303(14) O1 0.0503(13) 0.0413(10) 0.0321(11) 0.0032(8) 0.0038(9) -0.0138(9) O2 0.0448(12) 0.0383(10) 0.0415(12) -0.0021(9) -0.0024(10) 0.0032(9) O3 0.0520(14) 0.0532(13) 0.0591(15) 0.0015(11) 0.0104(12) 0.0090(11) N1 0.0327(13) 0.0325(11) 0.0467(15) 0.0055(10) 0.0022(11) 0.0014(10) C1 0.0379(17) 0.0358(15) 0.057(2) 0.0025(14) -0.0005(14) 0.0000(13) C2 0.046(2) 0.0332(16) 0.088(3) 0.0079(17) 0.0100(19) 0.0028(14) C3 0.072(3) 0.0431(18) 0.111(4) 0.033(2) 0.041(2) 0.0083(18) C4 0.077(3) 0.057(2) 0.081(3) 0.0269(19) 0.045(2) 0.0121(19) C5 0.0341(17) 0.0436(16) 0.067(2) 0.0159(15) 0.0192(16) 0.0040(13) C6 0.061(2) 0.0535(18) 0.051(2) 0.0089(15) 0.0273(17) 0.0079(16) C7 0.056(2) 0.0526(17) 0.0344(17) 0.0074(14) 0.0095(15) -0.0014(15) C8 0.0417(18) 0.0317(14) 0.0384(17) 0.0100(13) 0.0047(14) -0.0042(13) C9 0.049(2) 0.063(2) 0.051(2) 0.0165(16) -0.0062(16) -0.0025(16) _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 1.899(2) . ? Cu1 O1 1.927(2) 2_556 ? Cu1 O2 1.953(2) . ? Cu1 N1 2.001(2) . ? Cu1 C8 2.544(3) . ? Cu1 Cu1 3.0165(18) 2_556 ? O1 C7 1.396(4) . ? O1 Cu1 1.927(2) 2_556 ? O2 C8 1.271(3) . ? O3 C8 1.224(3) . ? N1 C5 1.341(4) . ? N1 C1 1.349(4) . ? C1 C2 1.383(4) . ? C1 H1 0.9500 . ? C2 C3 1.350(6) . ? C2 H2 0.9500 . ? C3 C4 1.385(5) . ? C3 H3 0.9500 . ? C4 C5 1.391(4) . ? C4 H4 0.9500 . ? C5 C6 1.503(4) . ? C6 C7 1.518(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.499(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 75.93(10) . 2_556 ? O1 Cu1 O2 170.72(8) . . ? O1 Cu1 O2 96.57(10) 2_556 . ? O1 Cu1 N1 94.28(10) . . ? O1 Cu1 N1 162.13(9) 2_556 . ? O2 Cu1 N1 94.35(10) . . ? O1 Cu1 C8 145.22(10) . . ? O1 Cu1 C8 98.38(9) 2_556 . ? O2 Cu1 C8 29.26(9) . . ? N1 Cu1 C8 98.06(10) . . ? O1 Cu1 Cu1 38.29(7) . 2_556 ? O1 Cu1 Cu1 37.64(6) 2_556 2_556 ? O2 Cu1 Cu1 133.98(7) . 2_556 ? N1 Cu1 Cu1 130.92(8) . 2_556 ? C8 Cu1 Cu1 127.61(7) . 2_556 ? C7 O1 Cu1 125.93(17) . . ? C7 O1 Cu1 129.98(17) . 2_556 ? Cu1 O1 Cu1 104.07(10) . 2_556 ? C8 O2 Cu1 102.06(18) . . ? C5 N1 C1 118.3(3) . . ? C5 N1 Cu1 122.76(19) . . ? C1 N1 Cu1 118.6(2) . . ? N1 C1 C2 123.0(3) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 119.1(3) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 118.6(3) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C3 C4 C5 120.5(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? N1 C5 C4 120.5(3) . . ? N1 C5 C6 116.9(3) . . ? C4 C5 C6 122.6(3) . . ? C5 C6 C7 114.4(3) . . ? C5 C6 H6A 108.7 . . ? C7 C6 H6A 108.7 . . ? C5 C6 H6B 108.7 . . ? C7 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? O1 C7 C6 111.4(3) . . ? O1 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? O1 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? O3 C8 O2 122.3(3) . . ? O3 C8 C9 120.9(3) . . ? O2 C8 C9 116.7(3) . . ? O3 C8 Cu1 73.70(17) . . ? O2 C8 Cu1 48.67(13) . . ? C9 C8 Cu1 165.3(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 O1 C7 178.1(3) 2_556 . . . ? O2 Cu1 O1 C7 -145.2(5) . . . . ? N1 Cu1 O1 C7 13.3(2) . . . . ? C8 Cu1 O1 C7 -97.4(3) . . . . ? Cu1 Cu1 O1 C7 178.1(3) 2_556 . . . ? O1 Cu1 O1 Cu1 0.0 2_556 . . 2_556 ? O2 Cu1 O1 Cu1 36.6(6) . . . 2_556 ? N1 Cu1 O1 Cu1 -164.83(10) . . . 2_556 ? C8 Cu1 O1 Cu1 84.42(18) . . . 2_556 ? O1 Cu1 O2 C8 59.8(6) . . . . ? O1 Cu1 O2 C8 95.44(18) 2_556 . . . ? N1 Cu1 O2 C8 -98.73(18) . . . . ? Cu1 Cu1 O2 C8 90.73(19) 2_556 . . . ? O1 Cu1 N1 C5 -22.5(2) . . . . ? O1 Cu1 N1 C5 -78.3(4) 2_556 . . . ? O2 Cu1 N1 C5 154.1(2) . . . . ? C8 Cu1 N1 C5 124.9(2) . . . . ? Cu1 Cu1 N1 C5 -34.9(3) 2_556 . . . ? O1 Cu1 N1 C1 150.7(2) . . . . ? O1 Cu1 N1 C1 94.9(3) 2_556 . . . ? O2 Cu1 N1 C1 -32.7(2) . . . . ? C8 Cu1 N1 C1 -61.9(2) . . . . ? Cu1 Cu1 N1 C1 138.27(19) 2_556 . . . ? C5 N1 C1 C2 -0.6(4) . . . . ? Cu1 N1 C1 C2 -174.0(2) . . . . ? N1 C1 C2 C3 1.4(5) . . . . ? C1 C2 C3 C4 -0.5(6) . . . . ? C2 C3 C4 C5 -1.1(6) . . . . ? C1 N1 C5 C4 -1.1(4) . . . . ? Cu1 N1 C5 C4 172.1(2) . . . . ? C1 N1 C5 C6 178.3(3) . . . . ? Cu1 N1 C5 C6 -8.6(4) . . . . ? C3 C4 C5 N1 2.0(5) . . . . ? C3 C4 C5 C6 -177.4(3) . . . . ? N1 C5 C6 C7 58.1(4) . . . . ? C4 C5 C6 C7 -122.6(3) . . . . ? Cu1 O1 C7 C6 24.6(4) . . . . ? Cu1 O1 C7 C6 -157.8(2) 2_556 . . . ? C5 C6 C7 O1 -66.0(4) . . . . ? Cu1 O2 C8 O3 -2.6(3) . . . . ? Cu1 O2 C8 C9 177.7(2) . . . . ? O1 Cu1 C8 O3 11.9(3) . . . . ? O1 Cu1 C8 O3 89.27(18) 2_556 . . . ? O2 Cu1 C8 O3 177.8(3) . . . . ? N1 Cu1 C8 O3 -97.75(18) . . . . ? Cu1 Cu1 C8 O3 63.0(2) 2_556 . . . ? O1 Cu1 C8 O2 -165.86(16) . . . . ? O1 Cu1 C8 O2 -88.48(18) 2_556 . . . ? N1 Cu1 C8 O2 84.50(19) . . . . ? Cu1 Cu1 C8 O2 -114.74(16) 2_556 . . . ? O1 Cu1 C8 C9 -174.0(8) . . . . ? O1 Cu1 C8 C9 -96.7(9) 2_556 . . . ? O2 Cu1 C8 C9 -8.2(8) . . . . ? N1 Cu1 C8 C9 76.3(9) . . . . ? Cu1 Cu1 C8 C9 -122.9(8) 2_556 . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2 O3 0.95 2.51 3.400(4) 155.2 1_565 C6 H6A O3 0.99 2.55 3.430(4) 147.5 2_656 C3 H3 O3 0.95 2.60 3.381(5) 140.3 2_666 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.348 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.064 #===END data_2a _database_code_depnum_ccdc_archive 'CCDC 737392' #TrackingRef 'ALL-REVISEDR3.cif'.2H2O #TrackingRef 'ALL-REVISEDR3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H28 Cu2 N2 O8' _chemical_formula_weight 539.51 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8669(2) _cell_length_b 10.2403(5) _cell_length_c 15.6326(8) _cell_angle_alpha 70.964(5) _cell_angle_beta 76.802(3) _cell_angle_gamma 76.981(4) _cell_volume 1143.37(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5653 _cell_measurement_theta_min 2.9811 _cell_measurement_theta_max 32.4689 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.567 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 1.906 _exptl_absorpt_correction_T_min 0.6683 _exptl_absorpt_correction_T_max 0.7377 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9588 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3969 _reflns_number_gt 2917 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0607P)^2^+0.6575P] 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 3969 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1183 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.119 _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 0.76585(6) 0.90232(6) 0.72452(4) 0.02299(17) Uani 1 1 d . . . Cu2 Cu 0.41647(6) 1.07254(6) 0.78353(4) 0.02259(17) Uani 1 1 d . . . O1 O 0.6365(4) 1.0908(3) 0.6990(2) 0.0242(7) Uani 1 1 d . . . O2 O 0.8603(4) 0.7033(3) 0.7629(2) 0.0297(8) Uani 1 1 d . . . O3 O 0.6869(4) 0.7081(4) 0.6688(3) 0.0431(9) Uani 1 1 d . . . O4 O 0.5476(4) 0.8874(3) 0.8121(2) 0.0263(7) Uani 1 1 d . . . O5 O 0.3213(4) 1.2722(3) 0.7549(2) 0.0252(7) Uani 1 1 d . . . O6 O 0.4231(4) 1.2265(4) 0.8838(2) 0.0392(9) Uani 1 1 d . . . N1 N 0.9916(4) 0.9592(4) 0.6496(3) 0.0241(9) Uani 1 1 d . . . N2 N 0.1863(4) 1.0122(4) 0.8509(2) 0.0247(9) Uani 1 1 d . . . C1 C 1.1451(5) 0.8821(5) 0.6759(3) 0.0265(10) Uani 1 1 d . . . H1 H 1.1410 0.7927 0.7198 0.032 Uiso 1 1 calc R . . C2 C 1.3059(6) 0.9261(6) 0.6427(3) 0.0324(12) Uani 1 1 d . . . H2 H 1.4108 0.8682 0.6622 0.039 Uiso 1 1 calc R . . C3 C 1.3110(6) 1.0570(6) 0.5802(4) 0.0361(13) Uani 1 1 d . . . H3 H 1.4200 1.0917 0.5575 0.043 Uiso 1 1 calc R . . C4 C 1.1577(6) 1.1374(6) 0.5505(3) 0.0330(12) Uani 1 1 d . . . H4 H 1.1607 1.2270 0.5068 0.040 Uiso 1 1 calc R . . C5 C 0.9981(5) 1.0857(5) 0.5854(3) 0.0253(10) Uani 1 1 d . . . C6 C 0.8283(6) 1.1696(5) 0.5552(3) 0.0291(11) Uani 1 1 d . . . H6A H 0.7760 1.1142 0.5296 0.035 Uiso 1 1 calc R . . H6B H 0.8543 1.2556 0.5057 0.035 Uiso 1 1 calc R . . C7 C 0.6940(6) 1.2105(5) 0.6329(3) 0.0273(10) Uani 1 1 d . . . H7A H 0.7483 1.2596 0.6621 0.033 Uiso 1 1 calc R . . H7B H 0.5912 1.2753 0.6080 0.033 Uiso 1 1 calc R . . C8 C 0.7877(6) 0.6416(5) 0.7252(4) 0.0322(12) Uani 1 1 d . . . C9 C 0.8294(7) 0.4813(6) 0.7536(5) 0.063(2) Uani 1 1 d . . . H9A H 0.7462 0.4446 0.7330 0.095 Uiso 1 1 calc R . . H9B H 0.8183 0.4454 0.8206 0.095 Uiso 1 1 calc R . . H9C H 0.9505 0.4513 0.7254 0.095 Uiso 1 1 calc R . . C10 C 0.0358(5) 1.0902(5) 0.8215(3) 0.0281(11) Uani 1 1 d . . . H10 H 0.0428 1.1750 0.7732 0.034 Uiso 1 1 calc R . . C11 C -0.1289(6) 1.0496(6) 0.8600(3) 0.0328(12) Uani 1 1 d . . . H11 H -0.2330 1.1059 0.8386 0.039 Uiso 1 1 calc R . . C12 C -0.1382(6) 0.9260(6) 0.9299(3) 0.0338(12) Uani 1 1 d . . . H12 H -0.2491 0.8960 0.9574 0.041 Uiso 1 1 calc R . . C13 C 0.0145(6) 0.8470(6) 0.9592(3) 0.0317(11) Uani 1 1 d . . . H13 H 0.0095 0.7613 1.0069 0.038 Uiso 1 1 calc R . . C14 C 0.1758(6) 0.8912(5) 0.9199(3) 0.0267(11) Uani 1 1 d . . . C15 C 0.3454(6) 0.8059(6) 0.9518(3) 0.0325(11) Uani 1 1 d . . . H15A H 0.3179 0.7187 0.9996 0.039 Uiso 1 1 calc R . . H15B H 0.3942 0.8596 0.9802 0.039 Uiso 1 1 calc R . . C16 C 0.4855(6) 0.7677(5) 0.8751(3) 0.0337(12) Uani 1 1 d . . . H16A H 0.5856 0.7012 0.9017 0.040 Uiso 1 1 calc R . . H16B H 0.4346 0.7210 0.8428 0.040 Uiso 1 1 calc R . . C17 C 0.3512(5) 1.3104(5) 0.8207(3) 0.0275(11) Uani 1 1 d . . . C18 C 0.2915(6) 1.4627(6) 0.8158(4) 0.0378(12) Uani 1 1 d . . . H18A H 0.3905 1.5144 0.7822 0.045 Uiso 1 1 calc R . . H18B H 0.1930 1.5007 0.7803 0.045 Uiso 1 1 calc R . . C19 C 0.2316(11) 1.4883(8) 0.9079(5) 0.080(2) Uani 1 1 d . . . H19A H 0.1274 1.4438 0.9397 0.121 Uiso 1 1 calc R . . H19B H 0.2010 1.5893 0.8999 0.121 Uiso 1 1 calc R . . H19C H 0.3270 1.4484 0.9443 0.121 Uiso 1 1 calc R . . O111 O 0.2627(4) 0.4801(4) 0.5886(3) 0.0451(9) Uani 1 1 d . . . O222 O 0.5392(5) 0.6294(4) 0.5533(3) 0.0523(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0142(3) 0.0277(4) 0.0300(3) -0.0141(3) -0.0034(2) -0.0009(2) Cu2 0.0149(3) 0.0268(4) 0.0277(3) -0.0123(3) -0.0022(2) -0.0015(2) O1 0.0168(14) 0.0234(18) 0.0284(17) -0.0077(14) 0.0001(13) 0.0010(13) O2 0.0221(16) 0.0282(19) 0.043(2) -0.0161(16) -0.0064(15) -0.0026(14) O3 0.0353(19) 0.052(3) 0.053(2) -0.033(2) -0.0164(18) 0.0074(17) O4 0.0210(15) 0.0248(18) 0.0297(17) -0.0085(15) 0.0016(13) -0.0020(13) O5 0.0205(15) 0.0247(18) 0.0295(17) -0.0105(15) -0.0027(13) 0.0007(13) O6 0.041(2) 0.039(2) 0.041(2) -0.0136(18) -0.0191(17) 0.0007(17) N1 0.0164(18) 0.033(2) 0.027(2) -0.0161(19) -0.0047(16) 0.0005(16) N2 0.0164(17) 0.036(2) 0.025(2) -0.0165(19) -0.0005(15) -0.0029(16) C1 0.021(2) 0.030(3) 0.033(3) -0.019(2) -0.007(2) 0.0029(19) C2 0.017(2) 0.047(3) 0.042(3) -0.027(3) -0.004(2) -0.001(2) C3 0.018(2) 0.054(4) 0.045(3) -0.027(3) 0.002(2) -0.011(2) C4 0.026(2) 0.041(3) 0.033(3) -0.013(2) 0.003(2) -0.011(2) C5 0.019(2) 0.035(3) 0.025(2) -0.016(2) -0.0025(19) -0.002(2) C6 0.023(2) 0.034(3) 0.028(3) -0.007(2) -0.003(2) -0.005(2) C7 0.021(2) 0.030(3) 0.028(2) -0.008(2) -0.001(2) -0.003(2) C8 0.016(2) 0.035(3) 0.050(3) -0.026(3) -0.001(2) 0.001(2) C9 0.033(3) 0.043(4) 0.133(6) -0.052(4) -0.021(4) 0.002(3) C10 0.021(2) 0.040(3) 0.026(2) -0.016(2) -0.0050(19) 0.000(2) C11 0.019(2) 0.051(4) 0.036(3) -0.026(3) -0.006(2) 0.000(2) C12 0.025(2) 0.050(4) 0.036(3) -0.025(3) 0.003(2) -0.016(2) C13 0.031(3) 0.036(3) 0.034(3) -0.018(2) 0.001(2) -0.012(2) C14 0.027(2) 0.035(3) 0.023(2) -0.016(2) 0.001(2) -0.006(2) C15 0.027(2) 0.040(3) 0.027(3) -0.010(2) 0.000(2) -0.004(2) C16 0.025(2) 0.032(3) 0.041(3) -0.012(2) -0.001(2) -0.002(2) C17 0.016(2) 0.031(3) 0.035(3) -0.013(2) 0.001(2) -0.0031(19) C18 0.030(3) 0.037(3) 0.052(3) -0.023(3) -0.009(2) -0.001(2) C19 0.108(6) 0.056(5) 0.077(5) -0.035(4) 0.028(5) -0.033(4) O111 0.039(2) 0.049(3) 0.045(2) -0.0064(19) -0.0118(18) -0.0073(18) O222 0.067(3) 0.058(3) 0.043(2) -0.015(2) -0.013(2) -0.028(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 O1 1.928(3) . ? Cu1 O4 1.937(3) . ? Cu1 O2 1.947(3) . ? Cu1 N1 1.984(4) . ? Cu1 Cu2 3.0292(7) . ? Cu2 O4 1.907(3) . ? Cu2 O1 1.928(3) . ? Cu2 O5 1.951(3) . ? Cu2 N2 1.994(4) . ? O1 C7 1.408(5) . ? O2 C8 1.278(5) . ? O3 C8 1.247(6) . ? O4 C16 1.405(6) . ? O5 C17 1.296(5) . ? O6 C17 1.231(6) . ? N1 C1 1.355(5) . ? N1 C5 1.359(6) . ? N2 C10 1.354(5) . ? N2 C14 1.357(6) . ? C1 C2 1.370(6) . ? C1 H1 0.9500 . ? C2 C3 1.380(7) . ? C2 H2 0.9500 . ? C3 C4 1.381(7) . ? C3 H3 0.9500 . ? C4 C5 1.397(6) . ? C4 H4 0.9500 . ? C5 C6 1.501(6) . ? C6 C7 1.521(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.533(7) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.392(6) . ? C10 H10 0.9500 . ? C11 C12 1.380(7) . ? C11 H11 0.9500 . ? C12 C13 1.371(7) . ? C12 H12 0.9500 . ? C13 C14 1.384(6) . ? C13 H13 0.9500 . ? C14 C15 1.512(6) . ? C15 C16 1.521(6) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.506(7) . ? C18 C19 1.498(8) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O4 75.83(12) . . ? O1 Cu1 O2 170.58(13) . . ? O4 Cu1 O2 94.91(13) . . ? O1 Cu1 N1 94.20(14) . . ? O4 Cu1 N1 164.01(14) . . ? O2 Cu1 N1 95.21(14) . . ? O1 Cu1 Cu2 38.22(9) . . ? O4 Cu1 Cu2 37.64(9) . . ? O2 Cu1 Cu2 132.44(9) . . ? N1 Cu1 Cu2 131.61(11) . . ? O4 Cu2 O1 76.55(12) . . ? O4 Cu2 O5 169.74(12) . . ? O1 Cu2 O5 96.35(13) . . ? O4 Cu2 N2 94.14(14) . . ? O1 Cu2 N2 162.40(14) . . ? O5 Cu2 N2 94.58(14) . . ? O4 Cu2 Cu1 38.35(9) . . ? O1 Cu2 Cu1 38.23(9) . . ? O5 Cu2 Cu1 134.36(9) . . ? N2 Cu2 Cu1 130.37(11) . . ? C7 O1 Cu2 129.8(3) . . ? C7 O1 Cu1 126.7(3) . . ? Cu2 O1 Cu1 103.54(14) . . ? C8 O2 Cu1 107.7(3) . . ? C16 O4 Cu2 126.1(3) . . ? C16 O4 Cu1 129.5(3) . . ? Cu2 O4 Cu1 104.01(15) . . ? C17 O5 Cu2 104.5(3) . . ? C1 N1 C5 118.2(4) . . ? C1 N1 Cu1 118.2(3) . . ? C5 N1 Cu1 122.3(3) . . ? C10 N2 C14 118.9(4) . . ? C10 N2 Cu2 118.3(3) . . ? C14 N2 Cu2 122.6(3) . . ? N1 C1 C2 123.6(5) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C1 C2 C3 118.1(4) . . ? C1 C2 H2 120.9 . . ? C3 C2 H2 120.9 . . ? C2 C3 C4 120.0(4) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 119.3(5) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 120.8(4) . . ? N1 C5 C6 118.0(4) . . ? C4 C5 C6 121.2(4) . . ? C5 C6 C7 112.8(4) . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? O1 C7 C6 110.5(4) . . ? O1 C7 H7A 109.6 . . ? C6 C7 H7A 109.6 . . ? O1 C7 H7B 109.6 . . ? C6 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? O3 C8 O2 121.9(5) . . ? O3 C8 C9 121.6(4) . . ? O2 C8 C9 116.5(4) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C11 121.9(5) . . ? N2 C10 H10 119.0 . . ? C11 C10 H10 119.0 . . ? C12 C11 C10 118.8(4) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C13 C12 C11 119.1(4) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C14 120.5(5) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? N2 C14 C13 120.7(4) . . ? N2 C14 C15 118.1(4) . . ? C13 C14 C15 121.2(4) . . ? C14 C15 C16 113.5(4) . . ? C14 C15 H15A 108.9 . . ? C16 C15 H15A 108.9 . . ? C14 C15 H15B 108.9 . . ? C16 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? O4 C16 C15 111.1(4) . . ? O4 C16 H16A 109.4 . . ? C15 C16 H16A 109.4 . . ? O4 C16 H16B 109.4 . . ? C15 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? O6 C17 O5 121.8(4) . . ? O6 C17 C18 122.1(4) . . ? O5 C17 C18 116.2(4) . . ? C19 C18 C17 113.7(5) . . ? C19 C18 H18A 108.8 . . ? C17 C18 H18A 108.8 . . ? C19 C18 H18B 108.8 . . ? C17 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 Cu2 O4 -176.7(2) . . . . ? O2 Cu1 Cu2 O4 5.20(19) . . . . ? N1 Cu1 Cu2 O4 -162.5(2) . . . . ? O4 Cu1 Cu2 O1 176.7(2) . . . . ? O2 Cu1 Cu2 O1 -178.14(19) . . . . ? N1 Cu1 Cu2 O1 14.18(19) . . . . ? O1 Cu1 Cu2 O5 -7.51(19) . . . . ? O4 Cu1 Cu2 O5 169.16(19) . . . . ? O2 Cu1 Cu2 O5 174.36(18) . . . . ? N1 Cu1 Cu2 O5 6.67(18) . . . . ? O1 Cu1 Cu2 N2 160.5(2) . . . . ? O4 Cu1 Cu2 N2 -22.84(19) . . . . ? O2 Cu1 Cu2 N2 -17.64(19) . . . . ? N1 Cu1 Cu2 N2 174.68(19) . . . . ? O4 Cu2 O1 C7 -178.4(4) . . . . ? O5 Cu2 O1 C7 -5.9(4) . . . . ? N2 Cu2 O1 C7 122.2(5) . . . . ? Cu1 Cu2 O1 C7 179.5(4) . . . . ? O4 Cu2 O1 Cu1 2.13(13) . . . . ? O5 Cu2 O1 Cu1 174.61(13) . . . . ? N2 Cu2 O1 Cu1 -57.3(5) . . . . ? O4 Cu1 O1 C7 178.4(3) . . . . ? O2 Cu1 O1 C7 -171.1(7) . . . . ? N1 Cu1 O1 C7 11.1(3) . . . . ? Cu2 Cu1 O1 C7 -179.5(4) . . . . ? O4 Cu1 O1 Cu2 -2.10(13) . . . . ? O2 Cu1 O1 Cu2 8.4(9) . . . . ? N1 Cu1 O1 Cu2 -169.42(14) . . . . ? O1 Cu1 O2 C8 70.0(9) . . . . ? O4 Cu1 O2 C8 80.3(3) . . . . ? N1 Cu1 O2 C8 -112.1(3) . . . . ? Cu2 Cu1 O2 C8 77.1(3) . . . . ? O1 Cu2 O4 C16 -175.2(4) . . . . ? O5 Cu2 O4 C16 137.9(7) . . . . ? N2 Cu2 O4 C16 -10.3(4) . . . . ? Cu1 Cu2 O4 C16 -173.0(4) . . . . ? O1 Cu2 O4 Cu1 -2.12(13) . . . . ? O5 Cu2 O4 Cu1 -49.0(8) . . . . ? N2 Cu2 O4 Cu1 162.75(15) . . . . ? O1 Cu1 O4 C16 174.8(4) . . . . ? O2 Cu1 O4 C16 -3.5(4) . . . . ? N1 Cu1 O4 C16 -132.5(5) . . . . ? Cu2 Cu1 O4 C16 172.7(4) . . . . ? O1 Cu1 O4 Cu2 2.13(13) . . . . ? O2 Cu1 O4 Cu2 -176.15(14) . . . . ? N1 Cu1 O4 Cu2 54.8(6) . . . . ? O4 Cu2 O5 C17 -54.4(8) . . . . ? O1 Cu2 O5 C17 -100.0(3) . . . . ? N2 Cu2 O5 C17 93.8(3) . . . . ? Cu1 Cu2 O5 C17 -95.3(3) . . . . ? O1 Cu1 N1 C1 148.8(3) . . . . ? O4 Cu1 N1 C1 98.2(6) . . . . ? O2 Cu1 N1 C1 -30.9(3) . . . . ? Cu2 Cu1 N1 C1 140.0(3) . . . . ? O1 Cu1 N1 C5 -17.8(3) . . . . ? O4 Cu1 N1 C5 -68.3(6) . . . . ? O2 Cu1 N1 C5 162.6(3) . . . . ? Cu2 Cu1 N1 C5 -26.5(4) . . . . ? O4 Cu2 N2 C10 -151.3(3) . . . . ? O1 Cu2 N2 C10 -94.2(6) . . . . ? O5 Cu2 N2 C10 34.1(3) . . . . ? Cu1 Cu2 N2 C10 -137.3(3) . . . . ? O4 Cu2 N2 C14 23.5(4) . . . . ? O1 Cu2 N2 C14 80.6(6) . . . . ? O5 Cu2 N2 C14 -151.1(3) . . . . ? Cu1 Cu2 N2 C14 37.5(4) . . . . ? C5 N1 C1 C2 1.4(6) . . . . ? Cu1 N1 C1 C2 -165.6(3) . . . . ? N1 C1 C2 C3 1.0(7) . . . . ? C1 C2 C3 C4 -2.2(7) . . . . ? C2 C3 C4 C5 0.9(7) . . . . ? C1 N1 C5 C4 -2.7(6) . . . . ? Cu1 N1 C5 C4 163.8(3) . . . . ? C1 N1 C5 C6 178.9(4) . . . . ? Cu1 N1 C5 C6 -14.6(5) . . . . ? C3 C4 C5 N1 1.6(7) . . . . ? C3 C4 C5 C6 179.9(4) . . . . ? N1 C5 C6 C7 62.4(6) . . . . ? C4 C5 C6 C7 -116.0(5) . . . . ? Cu2 O1 C7 C6 -153.4(3) . . . . ? Cu1 O1 C7 C6 26.0(5) . . . . ? C5 C6 C7 O1 -66.4(5) . . . . ? Cu1 O2 C8 O3 5.2(5) . . . . ? Cu1 O2 C8 C9 -174.2(4) . . . . ? C14 N2 C10 C11 -0.1(6) . . . . ? Cu2 N2 C10 C11 174.9(3) . . . . ? N2 C10 C11 C12 -0.2(7) . . . . ? C10 C11 C12 C13 -0.1(7) . . . . ? C11 C12 C13 C14 0.6(7) . . . . ? C10 N2 C14 C13 0.7(6) . . . . ? Cu2 N2 C14 C13 -174.1(3) . . . . ? C10 N2 C14 C15 -179.9(4) . . . . ? Cu2 N2 C14 C15 5.4(5) . . . . ? C12 C13 C14 N2 -1.0(7) . . . . ? C12 C13 C14 C15 179.6(4) . . . . ? N2 C14 C15 C16 -55.4(6) . . . . ? C13 C14 C15 C16 124.0(5) . . . . ? Cu2 O4 C16 C15 -29.2(5) . . . . ? Cu1 O4 C16 C15 159.5(3) . . . . ? C14 C15 C16 O4 67.1(5) . . . . ? Cu2 O5 C17 O6 -0.9(5) . . . . ? Cu2 O5 C17 C18 179.6(3) . . . . ? O6 C17 C18 C19 -32.5(7) . . . . ? O5 C17 C18 C19 147.0(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C11 H11 O1 0.95 2.67 3.316(5) 125.4 1_455 C2 H2 O3 0.95 2.41 3.329(6) 163.1 1_655 C4 H4 O3 0.95 2.66 3.341(6) 129.1 2_776 C12 H12 O6 0.95 2.61 3.401(6) 141.3 2_577 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.168 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.090 #===END data_2b _database_code_depnum_ccdc_archive 'CCDC 737393' #TrackingRef 'ALL-REVISEDR3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H24 Cu2 N2 O6' _chemical_formula_weight 503.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.855(2) _cell_length_b 10.137(3) _cell_length_c 13.539(4) _cell_angle_alpha 75.74(3) _cell_angle_beta 85.36(3) _cell_angle_gamma 77.02(3) _cell_volume 1017.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1266 _cell_measurement_theta_min 3.0083 _cell_measurement_theta_max 32.9787 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.643 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 2.128 _exptl_absorpt_correction_T_min 0.6403 _exptl_absorpt_correction_T_max 0.7408 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6443 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.1322 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3366 _reflns_number_gt 1812 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0548P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3366 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1126 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.1204 _refine_ls_wR_factor_gt 0.1111 _refine_ls_goodness_of_fit_ref 0.894 _refine_ls_restrained_S_all 0.894 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.83253(9) 0.33269(8) 0.19920(7) 0.0325(3) Uani 1 1 d . . . Cu2 Cu 1.16083(9) 0.11054(8) 0.25812(7) 0.0313(3) Uani 1 1 d . . . O1 O 0.9730(5) 0.1700(5) 0.1627(4) 0.0293(13) Uani 1 1 d . . . O2 O 0.7224(5) 0.4946(5) 0.2495(4) 0.0408(14) Uani 1 1 d . . . O3 O 0.9340(6) 0.5748(5) 0.1520(4) 0.0483(15) Uani 1 1 d . . . O4 O 1.0180(5) 0.2684(5) 0.2960(4) 0.0329(13) Uani 1 1 d . . . O5 O 1.2673(5) -0.0632(5) 0.2179(4) 0.0334(13) Uani 1 1 d . . . O6 O 1.1171(6) -0.1228(5) 0.3622(4) 0.0447(14) Uani 1 1 d . . . N1 N 0.6311(6) 0.3393(6) 0.1151(5) 0.0308(16) Uani 1 1 d . . . N2 N 1.3661(6) 0.1131(6) 0.3354(5) 0.0306(15) Uani 1 1 d . . . C1 C 0.4697(7) 0.3947(7) 0.1505(6) 0.0332(19) Uani 1 1 d . . . H1 H 0.4592 0.4435 0.2030 0.040 Uiso 1 1 calc R . . C2 C 0.3209(9) 0.3794(8) 0.1093(7) 0.044(2) Uani 1 1 d . . . H2 H 0.2086 0.4219 0.1314 0.052 Uiso 1 1 calc R . . C3 C 0.3348(9) 0.3050(8) 0.0387(7) 0.047(2) Uani 1 1 d . . . H3 H 0.2325 0.2911 0.0133 0.056 Uiso 1 1 calc R . . C4 C 0.4988(8) 0.2480(8) 0.0027(6) 0.041(2) Uani 1 1 d . . . H4 H 0.5103 0.1966 -0.0483 0.050 Uiso 1 1 calc R . . C5 C 0.6465(8) 0.2681(7) 0.0433(6) 0.033(2) Uani 1 1 d . . . C6 C 0.8271(7) 0.2149(7) 0.0024(5) 0.0351(19) Uani 1 1 d . . . H6A H 0.8834 0.2946 -0.0269 0.042 Uiso 1 1 calc R . . H6B H 0.8169 0.1692 -0.0529 0.042 Uiso 1 1 calc R . . C7 C 0.9427(8) 0.1107(7) 0.0858(6) 0.038(2) Uani 1 1 d . . . H7A H 0.8854 0.0318 0.1157 0.046 Uiso 1 1 calc R . . H7B H 1.0560 0.0734 0.0547 0.046 Uiso 1 1 calc R . . C8 C 0.8124(9) 0.5887(8) 0.2150(6) 0.043(2) Uani 1 1 d . . . C9 C 0.7618(9) 0.7192(9) 0.2529(8) 0.070(3) Uani 1 1 d . . . H9A H 0.8170 0.7048 0.3182 0.105 Uiso 1 1 calc R . . H9B H 0.6344 0.7430 0.2623 0.105 Uiso 1 1 calc R . . H9C H 0.8007 0.7954 0.2032 0.105 Uiso 1 1 calc R . . C10 C 1.5272(8) 0.0621(7) 0.3007(6) 0.037(2) Uani 1 1 d . . . H10 H 1.5375 0.0195 0.2447 0.044 Uiso 1 1 calc R . . C11 C 1.6770(8) 0.0694(8) 0.3429(6) 0.039(2) Uani 1 1 d . . . H11 H 1.7887 0.0314 0.3173 0.047 Uiso 1 1 calc R . . C12 C 1.6623(9) 0.1322(8) 0.4226(6) 0.044(2) Uani 1 1 d . . . H12 H 1.7641 0.1386 0.4529 0.052 Uiso 1 1 calc R . . C13 C 1.4968(9) 0.1869(7) 0.4593(6) 0.040(2) Uani 1 1 d . . . H13 H 1.4842 0.2328 0.5135 0.048 Uiso 1 1 calc R . . C14 C 1.3501(8) 0.1724(7) 0.4142(6) 0.034(2) Uani 1 1 d . . . C15 C 1.1691(8) 0.2301(8) 0.4537(6) 0.042(2) Uani 1 1 d . . . H15A H 1.1810 0.2769 0.5081 0.051 Uiso 1 1 calc R . . H15B H 1.1110 0.1518 0.4843 0.051 Uiso 1 1 calc R . . C16 C 1.0531(8) 0.3341(7) 0.3703(6) 0.036(2) Uani 1 1 d . . . H16A H 0.9417 0.3748 0.4016 0.043 Uiso 1 1 calc R . . H16B H 1.1127 0.4107 0.3374 0.043 Uiso 1 1 calc R . . C17 C 1.2138(8) -0.1550(8) 0.2901(6) 0.036(2) Uani 1 1 d . . . C18 C 1.2766(8) -0.3041(7) 0.2848(6) 0.041(2) Uani 1 1 d . . . H18A H 1.3871 -0.3127 0.2438 0.050 Uiso 1 1 calc R . . H18B H 1.1893 -0.3305 0.2488 0.050 Uiso 1 1 calc R . . C19 C 1.3073(11) -0.4052(9) 0.3874(8) 0.079(3) Uani 1 1 d . . . H19A H 1.4015 -0.3855 0.4210 0.119 Uiso 1 1 calc R . . H19B H 1.3403 -0.5005 0.3780 0.119 Uiso 1 1 calc R . . H19C H 1.2000 -0.3950 0.4296 0.119 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 0.0180(5) 0.0302(6) 0.0492(7) -0.0117(5) -0.0019(4) -0.0019(4) Cu2 0.0187(5) 0.0294(6) 0.0450(7) -0.0089(5) -0.0020(4) -0.0028(4) O1 0.020(2) 0.030(3) 0.041(4) -0.020(3) -0.003(2) 0.003(2) O2 0.020(2) 0.041(3) 0.063(4) -0.019(3) 0.001(2) -0.003(2) O3 0.031(3) 0.040(3) 0.064(4) -0.004(3) 0.005(3) 0.000(2) O4 0.024(2) 0.037(3) 0.039(4) -0.014(3) -0.003(2) -0.002(2) O5 0.022(2) 0.029(3) 0.046(4) -0.008(3) 0.001(2) -0.001(2) O6 0.037(3) 0.040(3) 0.059(4) -0.019(3) 0.013(3) -0.010(2) N1 0.020(3) 0.026(4) 0.043(5) -0.005(3) 0.001(3) -0.002(2) N2 0.017(3) 0.033(4) 0.041(4) -0.003(3) -0.002(3) -0.008(3) C1 0.019(4) 0.026(4) 0.048(6) -0.004(4) 0.000(3) 0.003(3) C2 0.021(4) 0.038(5) 0.066(7) 0.000(5) 0.001(4) -0.008(3) C3 0.021(4) 0.050(5) 0.065(7) -0.001(5) -0.011(4) -0.010(4) C4 0.029(4) 0.051(5) 0.043(5) -0.002(4) -0.008(3) -0.014(4) C5 0.025(4) 0.026(4) 0.044(6) -0.003(4) -0.002(3) -0.003(3) C6 0.022(4) 0.039(4) 0.039(5) -0.006(4) -0.003(3) 0.000(3) C7 0.026(4) 0.043(5) 0.048(6) -0.019(4) 0.001(3) -0.001(3) C8 0.020(4) 0.045(5) 0.063(6) -0.011(5) -0.009(4) 0.000(4) C9 0.038(5) 0.061(6) 0.125(10) -0.052(6) -0.007(5) -0.004(4) C10 0.026(4) 0.043(5) 0.037(5) 0.000(4) 0.002(3) -0.006(3) C11 0.023(4) 0.051(5) 0.036(6) 0.010(4) -0.003(3) -0.013(3) C12 0.030(4) 0.053(6) 0.043(6) 0.008(5) -0.012(4) -0.016(4) C13 0.040(5) 0.036(5) 0.046(6) -0.005(4) -0.015(4) -0.011(4) C14 0.030(4) 0.032(5) 0.034(6) 0.003(4) -0.002(3) -0.008(3) C15 0.040(4) 0.044(5) 0.045(6) -0.017(4) 0.000(4) -0.008(4) C16 0.030(4) 0.034(5) 0.045(6) -0.023(4) -0.004(3) 0.010(3) C17 0.015(3) 0.044(5) 0.047(6) -0.011(5) -0.005(3) -0.004(3) C18 0.028(4) 0.029(4) 0.069(6) -0.011(4) -0.006(4) -0.006(3) C19 0.083(7) 0.051(6) 0.107(9) -0.012(6) -0.019(6) -0.020(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.917(5) . ? Cu1 O2 1.929(5) . ? Cu1 O4 1.931(4) . ? Cu1 N1 2.002(5) . ? Cu1 Cu2 3.0325(15) . ? Cu2 O4 1.894(5) . ? Cu2 O1 1.932(4) . ? Cu2 O5 1.958(5) . ? Cu2 N2 2.000(5) . ? O1 C7 1.383(8) . ? O2 C8 1.288(8) . ? O3 C8 1.235(9) . ? O4 C16 1.411(8) . ? O5 C17 1.288(8) . ? O6 C17 1.250(9) . ? N1 C5 1.330(9) . ? N1 C1 1.366(8) . ? N2 C14 1.332(9) . ? N2 C10 1.349(8) . ? C1 C2 1.389(9) . ? C1 H1 0.9500 . ? C2 C3 1.340(10) . ? C2 H2 0.9500 . ? C3 C4 1.391(10) . ? C3 H3 0.9500 . ? C4 C5 1.397(8) . ? C4 H4 0.9500 . ? C5 C6 1.512(9) . ? C6 C7 1.537(9) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.496(10) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.373(8) . ? C10 H10 0.9500 . ? C11 C12 1.367(10) . ? C11 H11 0.9500 . ? C12 C13 1.397(10) . ? C12 H12 0.9500 . ? C13 C14 1.398(9) . ? C13 H13 0.9500 . ? C14 C15 1.519(9) . ? C15 C16 1.538(9) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.499(10) . ? C18 C19 1.510(10) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O2 170.71(18) . . ? O1 Cu1 O4 75.31(19) . . ? O2 Cu1 O4 95.6(2) . . ? O1 Cu1 N1 94.1(2) . . ? O2 Cu1 N1 95.2(2) . . ? O4 Cu1 N1 162.4(2) . . ? O1 Cu1 Cu2 38.21(13) . . ? O2 Cu1 Cu2 132.66(14) . . ? O4 Cu1 Cu2 37.12(15) . . ? N1 Cu1 Cu2 131.14(18) . . ? O4 Cu2 O1 75.80(18) . . ? O4 Cu2 O5 169.31(18) . . ? O1 Cu2 O5 96.65(19) . . ? O4 Cu2 N2 94.1(2) . . ? O1 Cu2 N2 160.9(2) . . ? O5 Cu2 N2 95.2(2) . . ? O4 Cu2 Cu1 37.97(13) . . ? O1 Cu2 Cu1 37.85(15) . . ? O5 Cu2 Cu1 134.22(13) . . ? N2 Cu2 Cu1 129.78(18) . . ? C7 O1 Cu1 127.0(4) . . ? C7 O1 Cu2 129.1(4) . . ? Cu1 O1 Cu2 103.9(2) . . ? C8 O2 Cu1 107.7(5) . . ? C16 O4 Cu2 126.9(3) . . ? C16 O4 Cu1 127.7(4) . . ? Cu2 O4 Cu1 104.9(2) . . ? C17 O5 Cu2 102.2(5) . . ? C5 N1 C1 120.4(6) . . ? C5 N1 Cu1 122.3(4) . . ? C1 N1 Cu1 115.7(5) . . ? C14 N2 C10 119.2(6) . . ? C14 N2 Cu2 122.6(4) . . ? C10 N2 Cu2 118.0(5) . . ? N1 C1 C2 119.7(8) . . ? N1 C1 H1 120.1 . . ? C2 C1 H1 120.1 . . ? C3 C2 C1 120.4(7) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 120.0(7) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 118.5(8) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? N1 C5 C4 121.0(6) . . ? N1 C5 C6 118.7(6) . . ? C4 C5 C6 120.3(8) . . ? C5 C6 C7 111.9(6) . . ? C5 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? C5 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? O1 C7 C6 112.6(6) . . ? O1 C7 H7A 109.1 . . ? C6 C7 H7A 109.1 . . ? O1 C7 H7B 109.1 . . ? C6 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? O3 C8 O2 122.3(8) . . ? O3 C8 C9 120.5(7) . . ? O2 C8 C9 117.1(7) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C11 122.7(8) . . ? N2 C10 H10 118.7 . . ? C11 C10 H10 118.7 . . ? C12 C11 C10 118.7(7) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C11 C12 C13 119.7(7) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C12 C13 C14 118.4(8) . . ? C12 C13 H13 120.8 . . ? C14 C13 H13 120.8 . . ? N2 C14 C13 121.3(7) . . ? N2 C14 C15 119.6(6) . . ? C13 C14 C15 119.1(8) . . ? C14 C15 C16 113.1(6) . . ? C14 C15 H15A 109.0 . . ? C16 C15 H15A 109.0 . . ? C14 C15 H15B 109.0 . . ? C16 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? O4 C16 C15 111.1(6) . . ? O4 C16 H16A 109.4 . . ? C15 C16 H16A 109.4 . . ? O4 C16 H16B 109.4 . . ? C15 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? O6 C17 O5 122.3(7) . . ? O6 C17 C18 121.2(7) . . ? O5 C17 C18 116.6(7) . . ? C17 C18 C19 114.2(7) . . ? C17 C18 H18A 108.7 . . ? C19 C18 H18A 108.7 . . ? C17 C18 H18B 108.7 . . ? C19 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 Cu2 O4 -177.6(4) . . . . ? O2 Cu1 Cu2 O4 4.8(3) . . . . ? N1 Cu1 Cu2 O4 -160.6(3) . . . . ? O2 Cu1 Cu2 O1 -177.5(3) . . . . ? O4 Cu1 Cu2 O1 177.6(4) . . . . ? N1 Cu1 Cu2 O1 17.1(3) . . . . ? O1 Cu1 Cu2 O5 -8.6(3) . . . . ? O2 Cu1 Cu2 O5 173.9(3) . . . . ? O4 Cu1 Cu2 O5 169.0(3) . . . . ? N1 Cu1 Cu2 O5 8.4(3) . . . . ? O1 Cu1 Cu2 N2 158.7(3) . . . . ? O2 Cu1 Cu2 N2 -18.8(3) . . . . ? O4 Cu1 Cu2 N2 -23.6(3) . . . . ? N1 Cu1 Cu2 N2 175.8(3) . . . . ? O2 Cu1 O1 C7 -169.1(12) . . . . ? O4 Cu1 O1 C7 178.0(5) . . . . ? N1 Cu1 O1 C7 12.3(5) . . . . ? Cu2 Cu1 O1 C7 179.5(6) . . . . ? O2 Cu1 O1 Cu2 11.3(14) . . . . ? O4 Cu1 O1 Cu2 -1.5(2) . . . . ? N1 Cu1 O1 Cu2 -167.2(2) . . . . ? O4 Cu2 O1 C7 -178.0(5) . . . . ? O5 Cu2 O1 C7 -5.7(5) . . . . ? N2 Cu2 O1 C7 122.3(8) . . . . ? Cu1 Cu2 O1 C7 -179.5(6) . . . . ? O4 Cu2 O1 Cu1 1.5(2) . . . . ? O5 Cu2 O1 Cu1 173.8(2) . . . . ? N2 Cu2 O1 Cu1 -58.2(8) . . . . ? O1 Cu1 O2 C8 65.8(14) . . . . ? O4 Cu1 O2 C8 78.2(4) . . . . ? N1 Cu1 O2 C8 -115.7(5) . . . . ? Cu2 Cu1 O2 C8 75.3(5) . . . . ? O1 Cu2 O4 C16 -174.2(5) . . . . ? O5 Cu2 O4 C16 139.9(10) . . . . ? N2 Cu2 O4 C16 -10.7(5) . . . . ? Cu1 Cu2 O4 C16 -172.7(6) . . . . ? O1 Cu2 O4 Cu1 -1.5(2) . . . . ? O5 Cu2 O4 Cu1 -47.4(12) . . . . ? N2 Cu2 O4 Cu1 162.0(2) . . . . ? O1 Cu1 O4 C16 174.1(5) . . . . ? O2 Cu1 O4 C16 -3.8(5) . . . . ? N1 Cu1 O4 C16 -131.5(8) . . . . ? Cu2 Cu1 O4 C16 172.6(6) . . . . ? O1 Cu1 O4 Cu2 1.5(2) . . . . ? O2 Cu1 O4 Cu2 -176.4(2) . . . . ? N1 Cu1 O4 Cu2 56.0(9) . . . . ? O4 Cu2 O5 C17 -58.0(12) . . . . ? O1 Cu2 O5 C17 -102.5(4) . . . . ? N2 Cu2 O5 C17 92.5(4) . . . . ? Cu1 Cu2 O5 C17 -97.2(4) . . . . ? O1 Cu1 N1 C5 -15.5(5) . . . . ? O2 Cu1 N1 C5 164.7(5) . . . . ? O4 Cu1 N1 C5 -67.6(10) . . . . ? Cu2 Cu1 N1 C5 -26.0(6) . . . . ? O1 Cu1 N1 C1 150.1(5) . . . . ? O2 Cu1 N1 C1 -29.7(5) . . . . ? O4 Cu1 N1 C1 98.0(9) . . . . ? Cu2 Cu1 N1 C1 139.6(4) . . . . ? O4 Cu2 N2 C14 23.5(6) . . . . ? O1 Cu2 N2 C14 80.5(9) . . . . ? O5 Cu2 N2 C14 -151.3(5) . . . . ? Cu1 Cu2 N2 C14 37.8(6) . . . . ? O4 Cu2 N2 C10 -151.2(5) . . . . ? O1 Cu2 N2 C10 -94.2(9) . . . . ? O5 Cu2 N2 C10 34.0(5) . . . . ? Cu1 Cu2 N2 C10 -136.9(4) . . . . ? C5 N1 C1 C2 -1.6(9) . . . . ? Cu1 N1 C1 C2 -167.5(5) . . . . ? N1 C1 C2 C3 3.2(10) . . . . ? C1 C2 C3 C4 -3.0(11) . . . . ? C2 C3 C4 C5 1.3(11) . . . . ? C1 N1 C5 C4 -0.1(10) . . . . ? Cu1 N1 C5 C4 164.8(5) . . . . ? C1 N1 C5 C6 176.9(6) . . . . ? Cu1 N1 C5 C6 -18.2(8) . . . . ? C3 C4 C5 N1 0.3(10) . . . . ? C3 C4 C5 C6 -176.6(6) . . . . ? N1 C5 C6 C7 62.2(8) . . . . ? C4 C5 C6 C7 -120.8(7) . . . . ? Cu1 O1 C7 C6 23.0(8) . . . . ? Cu2 O1 C7 C6 -157.7(4) . . . . ? C5 C6 C7 O1 -63.1(8) . . . . ? Cu1 O2 C8 O3 7.3(8) . . . . ? Cu1 O2 C8 C9 -173.9(5) . . . . ? C14 N2 C10 C11 -0.4(10) . . . . ? Cu2 N2 C10 C11 174.5(5) . . . . ? N2 C10 C11 C12 -0.8(10) . . . . ? C10 C11 C12 C13 0.2(10) . . . . ? C11 C12 C13 C14 1.5(10) . . . . ? C10 N2 C14 C13 2.1(10) . . . . ? Cu2 N2 C14 C13 -172.5(5) . . . . ? C10 N2 C14 C15 180.0(6) . . . . ? Cu2 N2 C14 C15 5.4(9) . . . . ? C12 C13 C14 N2 -2.7(10) . . . . ? C12 C13 C14 C15 179.4(6) . . . . ? N2 C14 C15 C16 -54.0(9) . . . . ? C13 C14 C15 C16 123.9(7) . . . . ? Cu2 O4 C16 C15 -28.0(8) . . . . ? Cu1 O4 C16 C15 160.9(4) . . . . ? C14 C15 C16 O4 64.5(8) . . . . ? Cu2 O5 C17 O6 0.3(7) . . . . ? Cu2 O5 C17 C18 -178.4(5) . . . . ? O6 C17 C18 C19 -33.3(9) . . . . ? O5 C17 C18 C19 145.4(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2 O4 0.95 2.90 3.485(9) 120.6 1_455 _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.937 _refine_diff_density_max 0.853 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.109 #===END data_3.2H2O _database_code_depnum_ccdc_archive 'CCDC 737394' #TrackingRef 'ALL-REVISEDR3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H30 Cu2 N2 O8' _chemical_formula_weight 553.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8291(10) _cell_length_b 10.3446(10) _cell_length_c 15.5698(15) _cell_angle_alpha 72.822(9) _cell_angle_beta 77.479(10) _cell_angle_gamma 78.022(10) _cell_volume 1162.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5254 _cell_measurement_theta_min 2.9971 _cell_measurement_theta_max 32.4346 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.582 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 1.877 _exptl_absorpt_correction_T_min 0.6215 _exptl_absorpt_correction_T_max 0.6828 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9216 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4079 _reflns_number_gt 3268 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0917P)^2^+2.5642P] 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 4079 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1741 _refine_ls_wR_factor_gt 0.1572 _refine_ls_goodness_of_fit_ref 1.192 _refine_ls_restrained_S_all 1.192 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.23660(8) 0.58647(6) 0.28020(4) 0.0201(2) Uani 1 1 d . . . Cu2 Cu 0.58468(8) 0.42226(6) 0.21831(4) 0.0201(2) Uani 1 1 d . . . O1 O 0.3662(4) 0.4043(3) 0.3017(2) 0.0207(7) Uani 1 1 d . . . O2 O 0.1421(5) 0.7799(3) 0.2449(2) 0.0273(8) Uani 1 1 d . . . O3 O 0.3157(5) 0.7744(4) 0.3409(3) 0.0356(10) Uani 1 1 d . . . O4 O 0.4525(4) 0.6020(3) 0.1941(2) 0.0216(8) Uani 1 1 d . . . O5 O 0.6799(5) 0.2278(3) 0.2432(2) 0.0246(8) Uani 1 1 d . . . O6 O 0.5823(6) 0.2729(4) 0.1127(3) 0.0357(10) Uani 1 1 d . . . N1 N 0.0126(6) 0.5310(4) 0.3537(3) 0.0227(9) Uani 1 1 d . . . N2 N 0.8118(6) 0.4829(4) 0.1511(3) 0.0231(9) Uani 1 1 d . . . C1 C -0.1411(7) 0.6084(5) 0.3293(4) 0.0259(11) Uani 1 1 d . . . H1 H -0.1364 0.6964 0.2879 0.031 Uiso 1 1 calc R . . C2 C -0.3026(7) 0.5648(6) 0.3619(4) 0.0295(12) Uani 1 1 d . . . H2 H -0.4073 0.6215 0.3434 0.035 Uiso 1 1 calc R . . C3 C -0.3101(8) 0.4374(6) 0.4219(4) 0.0333(13) Uani 1 1 d . . . H3 H -0.4202 0.4044 0.4448 0.040 Uiso 1 1 calc R . . C4 C -0.1575(7) 0.3587(6) 0.4482(4) 0.0311(12) Uani 1 1 d . . . H4 H -0.1613 0.2707 0.4897 0.037 Uiso 1 1 calc R . . C5 C 0.0027(7) 0.4072(5) 0.4144(3) 0.0256(11) Uani 1 1 d . . . C6 C 0.1726(8) 0.3245(6) 0.4426(4) 0.0302(12) Uani 1 1 d . . . H6A H 0.1463 0.2399 0.4899 0.036 Uiso 1 1 calc R . . H6B H 0.2271 0.3778 0.4699 0.036 Uiso 1 1 calc R . . C7 C 0.3030(7) 0.2865(5) 0.3639(4) 0.0261(12) Uani 1 1 d . . . H7A H 0.4039 0.2201 0.3873 0.031 Uiso 1 1 calc R . . H7B H 0.2450 0.2423 0.3321 0.031 Uiso 1 1 calc R . . C8 C 0.2154(7) 0.8389(5) 0.2855(3) 0.0274(12) Uani 1 1 d . . . C9 C 0.1737(9) 0.9933(6) 0.2630(4) 0.0379(14) Uani 1 1 d . . . H9A H 0.0489 1.0204 0.2892 0.045 Uiso 1 1 calc R . . H9B H 0.2498 1.0278 0.2917 0.045 Uiso 1 1 calc R . . C10 C 0.2013(11) 1.0574(6) 0.1641(5) 0.0561(19) Uani 1 1 d . . . H10A H 0.3254 1.0329 0.1381 0.084 Uiso 1 1 calc R . . H10B H 0.1722 1.1572 0.1530 0.084 Uiso 1 1 calc R . . H10C H 0.1247 1.0249 0.1355 0.084 Uiso 1 1 calc R . . C11 C 0.9645(7) 0.4092(5) 0.1778(3) 0.0247(11) Uani 1 1 d . . . H11 H 0.9589 0.3258 0.2242 0.030 Uiso 1 1 calc R . . C12 C 1.1284(7) 0.4498(6) 0.1409(4) 0.0273(12) Uani 1 1 d . . . H12 H 1.2329 0.3959 0.1615 0.033 Uiso 1 1 calc R . . C13 C 1.1358(8) 0.5714(6) 0.0728(4) 0.0312(12) Uani 1 1 d . . . H13 H 1.2463 0.6020 0.0457 0.037 Uiso 1 1 calc R . . C14 C 0.9824(8) 0.6469(5) 0.0452(4) 0.0296(12) Uani 1 1 d . . . H14 H 0.9860 0.7307 -0.0009 0.036 Uiso 1 1 calc R . . C15 C 0.8206(7) 0.6008(5) 0.0848(3) 0.0210(10) Uani 1 1 d . . . C16 C 0.6515(7) 0.6796(5) 0.0545(3) 0.0276(12) Uani 1 1 d . . . H16A H 0.6013 0.6236 0.0273 0.033 Uiso 1 1 calc R . . H16B H 0.6774 0.7637 0.0065 0.033 Uiso 1 1 calc R . . C17 C 0.5144(7) 0.7193(5) 0.1315(4) 0.0279(12) Uani 1 1 d . . . H17A H 0.5677 0.7666 0.1635 0.033 Uiso 1 1 calc R . . H17B H 0.4138 0.7834 0.1061 0.033 Uiso 1 1 calc R . . C18 C 0.6531(7) 0.1918(5) 0.1752(4) 0.0252(11) Uani 1 1 d . . . C19 C 0.7121(8) 0.0420(6) 0.1769(4) 0.0343(13) Uani 1 1 d . . . H19A H 0.8194 0.0078 0.2058 0.041 Uiso 1 1 calc R . . H19B H 0.6179 -0.0108 0.2150 0.041 Uiso 1 1 calc R . . C20 C 0.7520(10) 0.0165(7) 0.0840(5) 0.0489(17) Uani 1 1 d . . . H20A H 0.6459 0.0488 0.0552 0.073 Uiso 1 1 calc R . . H20B H 0.7881 -0.0818 0.0898 0.073 Uiso 1 1 calc R . . H20C H 0.8480 0.0659 0.0465 0.073 Uiso 1 1 calc R . . O111 O 0.7334(6) 0.0270(4) 0.4084(3) 0.0444(11) Uani 1 1 d . . . O222 O 0.4722(7) -0.1347(5) 0.4490(3) 0.0499(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0217(4) 0.0188(3) 0.0191(3) -0.0074(2) -0.0019(3) 0.0005(2) Cu2 0.0226(4) 0.0183(3) 0.0177(3) -0.0065(2) -0.0015(3) 0.0011(2) O1 0.0105(17) 0.0226(17) 0.0258(18) -0.0057(14) 0.0042(14) -0.0041(13) O2 0.030(2) 0.0221(18) 0.031(2) -0.0103(15) -0.0079(17) 0.0032(15) O3 0.043(2) 0.034(2) 0.033(2) -0.0170(17) -0.0133(19) 0.0062(18) O4 0.0110(17) 0.0222(17) 0.0260(18) -0.0046(14) 0.0070(15) -0.0030(13) O5 0.028(2) 0.0214(17) 0.0210(18) -0.0055(14) -0.0015(16) 0.0016(14) O6 0.048(3) 0.030(2) 0.032(2) -0.0100(17) -0.017(2) 0.0030(18) N1 0.025(2) 0.027(2) 0.017(2) -0.0118(17) -0.0016(18) -0.0001(18) N2 0.029(2) 0.024(2) 0.017(2) -0.0107(17) -0.0051(18) 0.0043(18) C1 0.022(3) 0.032(3) 0.026(3) -0.015(2) -0.004(2) 0.002(2) C2 0.018(3) 0.044(3) 0.032(3) -0.021(2) -0.005(2) 0.001(2) C3 0.025(3) 0.046(3) 0.032(3) -0.017(3) 0.003(2) -0.009(2) C4 0.027(3) 0.037(3) 0.027(3) -0.010(2) 0.005(2) -0.010(2) C5 0.033(3) 0.028(3) 0.017(2) -0.009(2) -0.001(2) -0.005(2) C6 0.035(3) 0.031(3) 0.021(3) -0.001(2) -0.004(2) -0.005(2) C7 0.029(3) 0.019(2) 0.025(3) -0.001(2) -0.002(2) -0.002(2) C8 0.031(3) 0.023(3) 0.024(3) -0.011(2) 0.004(2) 0.004(2) C9 0.043(4) 0.026(3) 0.046(3) -0.016(3) -0.007(3) 0.001(2) C10 0.074(5) 0.029(3) 0.053(4) -0.003(3) -0.003(4) 0.002(3) C11 0.030(3) 0.028(3) 0.017(2) -0.011(2) -0.002(2) -0.002(2) C12 0.021(3) 0.039(3) 0.026(3) -0.018(2) -0.003(2) 0.001(2) C13 0.029(3) 0.040(3) 0.029(3) -0.020(2) 0.003(2) -0.007(2) C14 0.042(3) 0.026(3) 0.021(3) -0.010(2) -0.001(2) -0.005(2) C15 0.022(3) 0.028(3) 0.017(2) -0.014(2) 0.003(2) -0.007(2) C16 0.030(3) 0.028(3) 0.020(3) -0.003(2) -0.002(2) -0.001(2) C17 0.028(3) 0.021(2) 0.028(3) -0.003(2) 0.004(2) -0.001(2) C18 0.024(3) 0.025(3) 0.027(3) -0.011(2) 0.003(2) -0.004(2) C19 0.037(3) 0.026(3) 0.042(3) -0.016(2) -0.003(3) -0.001(2) C20 0.059(5) 0.041(4) 0.051(4) -0.030(3) 0.016(3) -0.017(3) O111 0.045(3) 0.049(3) 0.035(2) 0.0010(19) -0.014(2) -0.007(2) O222 0.068(3) 0.053(3) 0.039(2) -0.014(2) -0.014(2) -0.024(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 O1 1.917(3) . ? Cu1 O4 1.919(3) . ? Cu1 O2 1.941(3) . ? Cu1 N1 1.969(5) . ? Cu1 Cu2 3.0245(9) . ? Cu2 O4 1.904(3) . ? Cu2 O1 1.917(3) . ? Cu2 O5 1.948(3) . ? Cu2 N2 1.980(5) . ? O1 C7 1.419(6) . ? O2 C8 1.277(7) . ? O3 C8 1.242(6) . ? O4 C17 1.414(6) . ? O5 C18 1.291(6) . ? O6 C18 1.231(6) . ? N1 C5 1.354(7) . ? N1 C1 1.361(6) . ? N2 C15 1.348(7) . ? N2 C11 1.354(7) . ? C1 C2 1.372(8) . ? C1 H1 0.9500 . ? C2 C3 1.376(8) . ? C2 H2 0.9500 . ? C3 C4 1.367(8) . ? C3 H3 0.9500 . ? C4 C5 1.386(8) . ? C4 H4 0.9500 . ? C5 C6 1.501(7) . ? C6 C7 1.507(8) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.511(7) . ? C9 C10 1.473(9) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.384(8) . ? C11 H11 0.9500 . ? C12 C13 1.387(8) . ? C12 H12 0.9500 . ? C13 C14 1.369(8) . ? C13 H13 0.9500 . ? C14 C15 1.397(8) . ? C14 H14 0.9500 . ? C15 C16 1.496(7) . ? C16 C17 1.519(7) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.516(7) . ? C19 C20 1.501(8) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O4 75.42(14) . . ? O1 Cu1 O2 170.25(15) . . ? O4 Cu1 O2 94.92(15) . . ? O1 Cu1 N1 94.84(16) . . ? O4 Cu1 N1 164.49(16) . . ? O2 Cu1 N1 94.89(17) . . ? O1 Cu1 Cu2 37.91(10) . . ? O4 Cu1 Cu2 37.55(10) . . ? O2 Cu1 Cu2 132.39(12) . . ? N1 Cu1 Cu2 131.98(12) . . ? O4 Cu2 O1 75.77(14) . . ? O4 Cu2 O5 169.62(15) . . ? O1 Cu2 O5 96.76(15) . . ? O4 Cu2 N2 94.31(15) . . ? O1 Cu2 N2 162.69(16) . . ? O5 Cu2 N2 94.65(16) . . ? O4 Cu2 Cu1 37.89(10) . . ? O1 Cu2 Cu1 37.91(10) . . ? O5 Cu2 Cu1 134.45(11) . . ? N2 Cu2 Cu1 130.32(12) . . ? C7 O1 Cu2 130.4(3) . . ? C7 O1 Cu1 125.3(3) . . ? Cu2 O1 Cu1 104.18(16) . . ? C8 O2 Cu1 106.4(3) . . ? C17 O4 Cu2 125.3(3) . . ? C17 O4 Cu1 129.8(3) . . ? Cu2 O4 Cu1 104.56(16) . . ? C18 O5 Cu2 104.1(3) . . ? C5 N1 C1 117.7(5) . . ? C5 N1 Cu1 123.1(4) . . ? C1 N1 Cu1 117.8(4) . . ? C15 N2 C11 118.3(5) . . ? C15 N2 Cu2 122.8(3) . . ? C11 N2 Cu2 118.7(3) . . ? N1 C1 C2 122.8(5) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C1 C2 C3 118.8(5) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C4 C3 C2 119.3(5) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 120.1(5) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? N1 C5 C4 121.2(5) . . ? N1 C5 C6 117.2(5) . . ? C4 C5 C6 121.6(5) . . ? C5 C6 C7 112.6(4) . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? O1 C7 C6 110.7(4) . . ? O1 C7 H7A 109.5 . . ? C6 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? O3 C8 O2 122.6(5) . . ? O3 C8 C9 120.9(5) . . ? O2 C8 C9 116.5(5) . . ? C10 C9 C8 112.5(5) . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9B 109.1 . . ? C8 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 C12 123.1(5) . . ? N2 C11 H11 118.5 . . ? C12 C11 H11 118.5 . . ? C11 C12 C13 118.2(5) . . ? C11 C12 H12 120.9 . . ? C13 C12 H12 120.9 . . ? C14 C13 C12 119.3(6) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 C15 120.1(5) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? N2 C15 C14 121.1(5) . . ? N2 C15 C16 117.7(5) . . ? C14 C15 C16 121.2(5) . . ? C15 C16 C17 113.1(4) . . ? C15 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? C15 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? O4 C17 C16 110.6(4) . . ? O4 C17 H17A 109.5 . . ? C16 C17 H17A 109.5 . . ? O4 C17 H17B 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? O6 C18 O5 122.6(5) . . ? O6 C18 C19 121.4(5) . . ? O5 C18 C19 116.0(4) . . ? C20 C19 C18 113.4(5) . . ? C20 C19 H19A 108.9 . . ? C18 C19 H19A 108.9 . . ? C20 C19 H19B 108.9 . . ? C18 C19 H19B 108.9 . . ? H19A C19 H19B 107.7 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 Cu2 O4 176.9(2) . . . . ? O2 Cu1 Cu2 O4 -4.5(2) . . . . ? N1 Cu1 Cu2 O4 163.0(2) . . . . ? O4 Cu1 Cu2 O1 -176.9(2) . . . . ? O2 Cu1 Cu2 O1 178.5(2) . . . . ? N1 Cu1 Cu2 O1 -13.9(2) . . . . ? O1 Cu1 Cu2 O5 7.5(2) . . . . ? O4 Cu1 Cu2 O5 -169.4(2) . . . . ? O2 Cu1 Cu2 O5 -173.95(19) . . . . ? N1 Cu1 Cu2 O5 -6.4(2) . . . . ? O1 Cu1 Cu2 N2 -161.5(2) . . . . ? O4 Cu1 Cu2 N2 21.6(2) . . . . ? O2 Cu1 Cu2 N2 17.1(2) . . . . ? N1 Cu1 Cu2 N2 -175.4(2) . . . . ? O4 Cu2 O1 C7 175.6(4) . . . . ? O5 Cu2 O1 C7 3.0(4) . . . . ? N2 Cu2 O1 C7 -127.9(5) . . . . ? Cu1 Cu2 O1 C7 177.6(5) . . . . ? O4 Cu2 O1 Cu1 -1.94(14) . . . . ? O5 Cu2 O1 Cu1 -174.61(15) . . . . ? N2 Cu2 O1 Cu1 54.5(6) . . . . ? O4 Cu1 O1 C7 -175.8(4) . . . . ? O2 Cu1 O1 C7 175.9(8) . . . . ? N1 Cu1 O1 C7 -8.1(4) . . . . ? Cu2 Cu1 O1 C7 -177.7(5) . . . . ? O4 Cu1 O1 Cu2 1.93(14) . . . . ? O2 Cu1 O1 Cu2 -6.4(9) . . . . ? N1 Cu1 O1 Cu2 169.66(17) . . . . ? O1 Cu1 O2 C8 -72.9(9) . . . . ? O4 Cu1 O2 C8 -81.0(3) . . . . ? N1 Cu1 O2 C8 111.0(3) . . . . ? Cu2 Cu1 O2 C8 -78.3(3) . . . . ? O1 Cu2 O4 C17 176.6(4) . . . . ? O5 Cu2 O4 C17 -138.7(7) . . . . ? N2 Cu2 O4 C17 11.0(4) . . . . ? Cu1 Cu2 O4 C17 174.6(5) . . . . ? O1 Cu2 O4 Cu1 1.94(14) . . . . ? O5 Cu2 O4 Cu1 46.7(9) . . . . ? N2 Cu2 O4 Cu1 -163.66(18) . . . . ? O1 Cu1 O4 C17 -176.2(5) . . . . ? O2 Cu1 O4 C17 2.4(4) . . . . ? N1 Cu1 O4 C17 131.4(6) . . . . ? Cu2 Cu1 O4 C17 -174.3(5) . . . . ? O1 Cu1 O4 Cu2 -1.95(14) . . . . ? O2 Cu1 O4 Cu2 176.64(16) . . . . ? N1 Cu1 O4 Cu2 -54.3(6) . . . . ? O4 Cu2 O5 C18 58.4(9) . . . . ? O1 Cu2 O5 C18 101.8(3) . . . . ? N2 Cu2 O5 C18 -91.3(3) . . . . ? Cu1 Cu2 O5 C18 97.1(3) . . . . ? O1 Cu1 N1 C5 16.1(4) . . . . ? O4 Cu1 N1 C5 66.4(7) . . . . ? O2 Cu1 N1 C5 -164.6(4) . . . . ? Cu2 Cu1 N1 C5 24.6(4) . . . . ? O1 Cu1 N1 C1 -150.2(4) . . . . ? O4 Cu1 N1 C1 -99.9(6) . . . . ? O2 Cu1 N1 C1 29.2(4) . . . . ? Cu2 Cu1 N1 C1 -141.6(3) . . . . ? O4 Cu2 N2 C15 -23.2(4) . . . . ? O1 Cu2 N2 C15 -77.3(6) . . . . ? O5 Cu2 N2 C15 151.5(4) . . . . ? Cu1 Cu2 N2 C15 -36.3(4) . . . . ? O4 Cu2 N2 C11 150.9(4) . . . . ? O1 Cu2 N2 C11 96.8(6) . . . . ? O5 Cu2 N2 C11 -34.4(4) . . . . ? Cu1 Cu2 N2 C11 137.8(3) . . . . ? C5 N1 C1 C2 -1.5(7) . . . . ? Cu1 N1 C1 C2 165.5(4) . . . . ? N1 C1 C2 C3 0.0(8) . . . . ? C1 C2 C3 C4 0.9(8) . . . . ? C2 C3 C4 C5 -0.2(8) . . . . ? C1 N1 C5 C4 2.2(7) . . . . ? Cu1 N1 C5 C4 -164.1(4) . . . . ? C1 N1 C5 C6 -178.5(4) . . . . ? Cu1 N1 C5 C6 15.3(6) . . . . ? C3 C4 C5 N1 -1.4(8) . . . . ? C3 C4 C5 C6 179.3(5) . . . . ? N1 C5 C6 C7 -62.6(6) . . . . ? C4 C5 C6 C7 116.8(6) . . . . ? Cu2 O1 C7 C6 153.6(3) . . . . ? Cu1 O1 C7 C6 -29.3(6) . . . . ? C5 C6 C7 O1 68.3(6) . . . . ? Cu1 O2 C8 O3 -4.7(6) . . . . ? Cu1 O2 C8 C9 175.4(4) . . . . ? O3 C8 C9 C10 129.0(6) . . . . ? O2 C8 C9 C10 -51.1(8) . . . . ? C15 N2 C11 C12 0.4(7) . . . . ? Cu2 N2 C11 C12 -173.9(4) . . . . ? N2 C11 C12 C13 -0.3(7) . . . . ? C11 C12 C13 C14 0.4(8) . . . . ? C12 C13 C14 C15 -0.6(8) . . . . ? C11 N2 C15 C14 -0.6(7) . . . . ? Cu2 N2 C15 C14 173.5(4) . . . . ? C11 N2 C15 C16 178.7(4) . . . . ? Cu2 N2 C15 C16 -7.1(6) . . . . ? C13 C14 C15 N2 0.7(7) . . . . ? C13 C14 C15 C16 -178.6(5) . . . . ? N2 C15 C16 C17 57.9(6) . . . . ? C14 C15 C16 C17 -122.7(5) . . . . ? Cu2 O4 C17 C16 28.6(6) . . . . ? Cu1 O4 C17 C16 -158.1(3) . . . . ? C15 C16 C17 O4 -68.3(6) . . . . ? Cu2 O5 C18 O6 0.3(6) . . . . ? Cu2 O5 C18 C19 -179.0(4) . . . . ? O6 C18 C19 C20 25.6(8) . . . . ? O5 C18 C19 C20 -155.1(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2 O3 0.95 2.40 3.325(7) 163.1 1_455 C4 H4 O3 0.95 2.60 3.238(7) 124.9 2_566 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.235 _refine_diff_density_min -1.445 _refine_diff_density_rms 0.144 #===END data_4-HEAT _database_code_depnum_ccdc_archive 'CCDC 737395' #TrackingRef 'ALL-REVISEDR3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H52 Cu4 N4 O12' _chemical_formula_weight 1035.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 11.699(2) _cell_length_b 9.5859(12) _cell_length_c 18.9713(11) _cell_angle_alpha 90.00 _cell_angle_beta 96.559(10) _cell_angle_gamma 90.00 _cell_volume 2113.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4156 _cell_measurement_theta_min 2.9298 _cell_measurement_theta_max 32.9033 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.626 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 2.052 _exptl_absorpt_correction_T_min 0.5974 _exptl_absorpt_correction_T_max 0.6610 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14593 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3701 _reflns_number_gt 2914 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0448P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3701 _refine_ls_number_parameters 293 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.0836 _refine_ls_wR_factor_gt 0.0784 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 1.21833(3) 0.09931(5) 0.03792(2) 0.01953(13) Uani 1 1 d . . . Cu2 Cu 0.97759(3) 0.05751(4) 0.08035(2) 0.01758(13) Uani 1 1 d . . . O1 O 1.05623(18) 0.1384(2) 0.00038(11) 0.0180(5) Uani 1 1 d . . . O2 O 1.3738(2) 0.0691(3) 0.08696(12) 0.0242(6) Uani 1 1 d . . . O3 O 1.3434(2) 0.2884(3) 0.11669(14) 0.0388(7) Uani 1 1 d . . . O4 O 1.13586(19) 0.0267(3) 0.11158(11) 0.0256(6) Uani 1 1 d . . . O5 O 0.82375(19) 0.1020(2) 0.03508(11) 0.0193(5) Uani 1 1 d . . . O6 O 0.8214(2) 0.3074(3) 0.08916(13) 0.0315(6) Uani 1 1 d . A . N1 N 1.2787(2) 0.1937(3) -0.04291(14) 0.0194(6) Uani 1 1 d . . . N2 N 0.9294(2) -0.0070(3) 0.17635(13) 0.0205(7) Uani 1 1 d . . . C1 C 1.3695(3) 0.1423(4) -0.07145(18) 0.0244(8) Uani 1 1 d . . . H1 H 1.4074 0.0625 -0.0503 0.029 Uiso 1 1 calc R . . C2 C 1.4101(3) 0.2002(4) -0.12998(19) 0.0299(9) Uani 1 1 d . . . H2 H 1.4752 0.1621 -0.1488 0.036 Uiso 1 1 calc R . . C3 C 1.3539(3) 0.3147(4) -0.1604(2) 0.0350(10) Uani 1 1 d . . . H3 H 1.3783 0.3555 -0.2017 0.042 Uiso 1 1 calc R . . C4 C 1.2615(3) 0.3704(4) -0.13047(19) 0.0323(9) Uani 1 1 d . . . H4 H 1.2230 0.4506 -0.1508 0.039 Uiso 1 1 calc R . . C5 C 1.2257(3) 0.3091(4) -0.07114(17) 0.0222(8) Uani 1 1 d . . . C6 C 1.1284(3) 0.3649(4) -0.03408(18) 0.0227(8) Uani 1 1 d . . . H6A H 1.1019 0.4539 -0.0568 0.027 Uiso 1 1 calc R . . H6B H 1.1578 0.3855 0.0158 0.027 Uiso 1 1 calc R . . C7 C 1.0263(3) 0.2679(4) -0.03471(18) 0.0233(8) Uani 1 1 d . . . H7A H 0.9654 0.3143 -0.0110 0.028 Uiso 1 1 calc R . . H7B H 0.9948 0.2489 -0.0845 0.028 Uiso 1 1 calc R . . C8 C 1.4043(3) 0.1833(4) 0.11912(18) 0.0258(9) Uani 1 1 d . . . C9 C 1.5203(3) 0.1802(5) 0.1627(2) 0.0366(10) Uani 1 1 d . . . H9A H 1.5182 0.1101 0.2009 0.044 Uiso 1 1 calc R . . H9B H 1.5784 0.1492 0.1320 0.044 Uiso 1 1 calc R . . C10 C 1.5581(4) 0.3169(6) 0.1958(3) 0.0632(15) Uani 1 1 d . . . H10A H 1.5688 0.3847 0.1584 0.095 Uiso 1 1 calc R . . H10B H 1.6310 0.3043 0.2261 0.095 Uiso 1 1 calc R . . H10C H 1.4994 0.3512 0.2244 0.095 Uiso 1 1 calc R . . C11 C 0.8233(3) 0.0277(4) 0.19118(18) 0.0259(9) Uani 1 1 d . . . H11 H 0.7750 0.0786 0.1566 0.031 Uiso 1 1 calc R . . C12 C 0.7814(3) -0.0065(4) 0.25344(18) 0.0345(10) Uani 1 1 d . . . H12 H 0.7057 0.0201 0.2614 0.041 Uiso 1 1 calc R . . C13 C 0.8499(3) -0.0798(4) 0.3042(2) 0.0368(10) Uani 1 1 d . . . H13 H 0.8222 -0.1059 0.3475 0.044 Uiso 1 1 calc R . . C14 C 0.9590(3) -0.1143(4) 0.29098(19) 0.0318(10) Uani 1 1 d . . . H14 H 1.0081 -0.1636 0.3258 0.038 Uiso 1 1 calc R . . C15 C 0.9986(3) -0.0777(4) 0.22703(17) 0.0237(8) Uani 1 1 d . . . C16 C 1.1189(3) -0.1153(4) 0.21431(18) 0.0258(9) Uani 1 1 d . . . H16A H 1.1159 -0.1971 0.1822 0.031 Uiso 1 1 calc R . . H16B H 1.1623 -0.1433 0.2600 0.031 Uiso 1 1 calc R . . C17 C 1.1833(3) 0.0005(4) 0.18242(17) 0.0262(9) Uani 1 1 d . . . H17A H 1.1792 0.0863 0.2110 0.031 Uiso 1 1 calc R . . H17B H 1.2653 -0.0258 0.1833 0.031 Uiso 1 1 calc R . . C18 C 0.7815(3) 0.2253(4) 0.04328(17) 0.0218(8) Uani 1 1 d U . . C19A C 0.668(3) 0.266(3) -0.0064(17) 0.040(4) Uani 0.516(10) 1 d PU A 1 H19A H 0.6822 0.2414 -0.0553 0.048 Uiso 0.516(10) 1 calc PR A 1 H19B H 0.6073 0.2006 0.0061 0.048 Uiso 0.516(10) 1 calc PR A 1 C20A C 0.6197(9) 0.3906(10) -0.0104(7) 0.078(5) Uani 0.516(10) 1 d PU A 1 H20A H 0.6482 0.4451 0.0316 0.116 Uiso 0.516(10) 1 calc PR A 1 H20B H 0.5359 0.3810 -0.0128 0.116 Uiso 0.516(10) 1 calc PR A 1 H20C H 0.6393 0.4384 -0.0531 0.116 Uiso 0.516(10) 1 calc PR A 1 C19B C 0.689(3) 0.256(3) -0.0095(18) 0.042(6) Uani 0.484(10) 1 d PU A 2 H19C H 0.6477 0.1667 -0.0210 0.051 Uiso 0.484(10) 1 calc PR A 2 H19D H 0.6347 0.3165 0.0130 0.051 Uiso 0.484(10) 1 calc PR A 2 C20B C 0.7053(9) 0.3166(12) -0.0726(5) 0.060(4) Uani 0.484(10) 1 d PU A 2 H20D H 0.7419 0.4078 -0.0636 0.089 Uiso 0.484(10) 1 calc PR A 2 H20E H 0.6310 0.3286 -0.1014 0.089 Uiso 0.484(10) 1 calc PR A 2 H20F H 0.7550 0.2569 -0.0979 0.089 Uiso 0.484(10) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0178(2) 0.0221(3) 0.0186(2) 0.00250(18) 0.00166(17) -0.00055(18) Cu2 0.0180(2) 0.0188(3) 0.0158(2) 0.00210(17) 0.00136(16) 0.00023(18) O1 0.0170(12) 0.0139(13) 0.0228(12) 0.0050(10) 0.0016(10) 0.0010(10) O2 0.0239(13) 0.0243(15) 0.0240(12) -0.0008(11) 0.0005(10) -0.0018(11) O3 0.0354(16) 0.0376(19) 0.0430(16) -0.0111(13) 0.0028(13) 0.0076(14) O4 0.0192(12) 0.0399(17) 0.0171(11) 0.0112(11) -0.0004(10) 0.0009(12) O5 0.0193(12) 0.0166(14) 0.0217(12) 0.0008(10) 0.0015(10) 0.0013(11) O6 0.0411(16) 0.0198(15) 0.0340(15) -0.0051(12) 0.0054(12) -0.0008(12) N1 0.0185(15) 0.0206(18) 0.0190(14) -0.0024(12) 0.0014(12) -0.0031(13) N2 0.0230(16) 0.0191(17) 0.0192(14) 0.0004(12) 0.0013(12) -0.0008(13) C1 0.0197(19) 0.024(2) 0.0291(19) -0.0025(16) 0.0028(15) -0.0011(16) C2 0.027(2) 0.034(3) 0.030(2) -0.0045(17) 0.0104(17) -0.0021(18) C3 0.043(2) 0.036(3) 0.029(2) 0.0078(18) 0.0176(18) 0.000(2) C4 0.040(2) 0.029(2) 0.029(2) 0.0095(17) 0.0092(18) 0.0019(19) C5 0.0269(19) 0.016(2) 0.0237(18) -0.0037(15) 0.0050(15) -0.0040(16) C6 0.030(2) 0.014(2) 0.0250(18) 0.0007(14) 0.0063(16) 0.0004(16) C7 0.0222(18) 0.019(2) 0.0286(19) 0.0042(16) 0.0042(15) 0.0048(16) C8 0.0205(19) 0.036(3) 0.0220(19) 0.0021(17) 0.0079(15) -0.0018(18) C9 0.027(2) 0.050(3) 0.032(2) -0.0108(19) -0.0006(17) -0.006(2) C10 0.053(3) 0.076(4) 0.060(3) -0.020(3) 0.004(3) -0.019(3) C11 0.0227(19) 0.031(2) 0.0235(18) 0.0062(16) 0.0024(15) -0.0007(17) C12 0.026(2) 0.051(3) 0.027(2) 0.0035(19) 0.0086(17) -0.004(2) C13 0.035(2) 0.052(3) 0.0244(19) 0.0055(19) 0.0072(17) -0.013(2) C14 0.033(2) 0.041(3) 0.0210(18) 0.0122(17) -0.0020(16) -0.0061(19) C15 0.028(2) 0.022(2) 0.0208(17) 0.0022(15) 0.0010(15) -0.0036(16) C16 0.027(2) 0.029(2) 0.0207(18) 0.0044(16) -0.0015(15) 0.0033(17) C17 0.0236(19) 0.038(2) 0.0168(16) 0.0066(16) 0.0002(15) 0.0044(17) C18 0.0200(19) 0.025(2) 0.0216(18) 0.0057(16) 0.0061(15) 0.0012(17) C19A 0.016(7) 0.057(9) 0.045(7) 0.008(6) -0.003(5) 0.028(6) C20A 0.066(7) 0.038(6) 0.115(10) -0.010(6) -0.046(7) 0.008(5) C19B 0.032(15) 0.021(8) 0.072(9) 0.006(7) -0.004(9) 0.010(9) C20B 0.055(7) 0.068(9) 0.052(6) 0.002(5) -0.009(5) -0.017(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 1.917(2) . ? Cu1 O2 1.967(2) . ? Cu1 N1 1.979(3) . ? Cu1 O1 1.984(2) . ? Cu1 O5 2.394(2) 3_755 ? Cu1 Cu2 3.0428(7) . ? Cu2 O4 1.902(2) . ? Cu2 O5 1.951(2) . ? Cu2 O1 2.017(2) . ? Cu2 N2 2.062(3) . ? Cu2 O1 2.427(2) 3_755 ? O1 C7 1.432(4) . ? O1 Cu2 2.427(2) 3_755 ? O2 C8 1.284(4) . ? O3 C8 1.232(4) . ? O4 C17 1.417(4) . ? O5 C18 1.297(4) . ? O5 Cu1 2.394(2) 3_755 ? O6 C18 1.225(4) . ? N1 C1 1.341(4) . ? N1 C5 1.349(4) . ? N2 C11 1.345(4) . ? N2 C15 1.365(4) . ? C1 C2 1.374(5) . ? C1 H1 0.9500 . ? C2 C3 1.372(5) . ? C2 H2 0.9500 . ? C3 C4 1.384(5) . ? C3 H3 0.9500 . ? C4 C5 1.377(5) . ? C4 H4 0.9500 . ? C5 C6 1.503(5) . ? C6 C7 1.513(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.507(5) . ? C9 C10 1.498(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.370(5) . ? C11 H11 0.9500 . ? C12 C13 1.373(5) . ? C12 H12 0.9500 . ? C13 C14 1.370(6) . ? C13 H13 0.9500 . ? C14 C15 1.392(5) . ? C14 H14 0.9500 . ? C15 C16 1.499(5) . ? C16 C17 1.507(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19B 1.42(3) . ? C18 C19A 1.59(3) . ? C19A C20A 1.32(3) . ? C19A H19A 0.9900 . ? C19A H19B 0.9900 . ? C20A H20A 0.9800 . ? C20A H20B 0.9800 . ? C20A H20C 0.9800 . ? C19B C20B 1.36(3) . ? C19B H19C 0.9900 . ? C19B H19D 0.9900 . ? C20B H20D 0.9800 . ? C20B H20E 0.9800 . ? C20B H20F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cu1 O2 96.71(9) . . ? O4 Cu1 N1 169.91(11) . . ? O2 Cu1 N1 92.38(10) . . ? O4 Cu1 O1 77.89(9) . . ? O2 Cu1 O1 172.62(10) . . ? N1 Cu1 O1 92.66(10) . . ? O4 Cu1 O5 92.39(9) . 3_755 ? O2 Cu1 O5 105.83(9) . 3_755 ? N1 Cu1 O5 89.33(10) . 3_755 ? O1 Cu1 O5 79.61(8) . 3_755 ? O4 Cu1 Cu2 37.00(6) . . ? O2 Cu1 Cu2 133.55(7) . . ? N1 Cu1 Cu2 133.48(8) . . ? O1 Cu1 Cu2 40.90(6) . . ? O5 Cu1 Cu2 84.92(6) 3_755 . ? O4 Cu2 O5 170.99(9) . . ? O4 Cu2 O1 77.44(9) . . ? O5 Cu2 O1 93.55(9) . . ? O4 Cu2 N2 91.89(10) . . ? O5 Cu2 N2 97.05(10) . . ? O1 Cu2 N2 166.86(10) . . ? O4 Cu2 O1 99.16(9) . 3_755 ? O5 Cu2 O1 79.39(8) . 3_755 ? O1 Cu2 O1 83.02(9) . 3_755 ? N2 Cu2 O1 106.50(10) . 3_755 ? O4 Cu2 Cu1 37.36(7) . . ? O5 Cu2 Cu1 133.64(7) . . ? O1 Cu2 Cu1 40.09(6) . . ? N2 Cu2 Cu1 128.89(8) . . ? O1 Cu2 Cu1 91.38(5) 3_755 . ? C7 O1 Cu1 120.24(19) . . ? C7 O1 Cu2 125.04(19) . . ? Cu1 O1 Cu2 99.02(9) . . ? C7 O1 Cu2 111.31(18) . 3_755 ? Cu1 O1 Cu2 99.23(9) . 3_755 ? Cu2 O1 Cu2 96.98(9) . 3_755 ? C8 O2 Cu1 106.9(2) . . ? C17 O4 Cu2 125.8(2) . . ? C17 O4 Cu1 125.5(2) . . ? Cu2 O4 Cu1 105.65(10) . . ? C18 O5 Cu2 119.4(2) . . ? C18 O5 Cu1 138.4(2) . 3_755 ? Cu2 O5 Cu1 101.35(10) . 3_755 ? C1 N1 C5 119.4(3) . . ? C1 N1 Cu1 121.0(2) . . ? C5 N1 Cu1 119.6(2) . . ? C11 N2 C15 117.6(3) . . ? C11 N2 Cu2 117.5(2) . . ? C15 N2 Cu2 124.8(2) . . ? N1 C1 C2 122.8(4) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 118.0(3) . . ? C3 C2 H2 121.0 . . ? C1 C2 H2 121.0 . . ? C2 C3 C4 119.7(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 119.7(4) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? N1 C5 C4 120.3(3) . . ? N1 C5 C6 116.4(3) . . ? C4 C5 C6 123.3(3) . . ? C5 C6 C7 114.7(3) . . ? C5 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? C5 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? O1 C7 C6 112.2(3) . . ? O1 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? O1 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? O3 C8 O2 123.5(3) . . ? O3 C8 C9 121.1(4) . . ? O2 C8 C9 115.4(3) . . ? C10 C9 C8 114.7(4) . . ? C10 C9 H9A 108.6 . . ? C8 C9 H9A 108.6 . . ? C10 C9 H9B 108.6 . . ? C8 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 C12 123.4(3) . . ? N2 C11 H11 118.3 . . ? C12 C11 H11 118.3 . . ? C11 C12 C13 119.3(4) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C14 C13 C12 118.5(4) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? C13 C14 C15 120.6(3) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? N2 C15 C14 120.6(3) . . ? N2 C15 C16 119.9(3) . . ? C14 C15 C16 119.5(3) . . ? C15 C16 C17 114.2(3) . . ? C15 C16 H16A 108.7 . . ? C17 C16 H16A 108.7 . . ? C15 C16 H16B 108.7 . . ? C17 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? O4 C17 C16 110.6(3) . . ? O4 C17 H17A 109.5 . . ? C16 C17 H17A 109.5 . . ? O4 C17 H17B 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? O6 C18 O5 123.4(3) . . ? O6 C18 C19B 124.5(13) . . ? O5 C18 C19B 111.9(13) . . ? O6 C18 C19A 119.4(11) . . ? O5 C18 C19A 117.1(11) . . ? C19B C18 C19A 8(2) . . ? C20A C19A C18 125(2) . . ? C20A C19A H19A 106.0 . . ? C18 C19A H19A 106.0 . . ? C20A C19A H19B 106.0 . . ? C18 C19A H19B 106.0 . . ? H19A C19A H19B 106.3 . . ? C20B C19B C18 122(2) . . ? C20B C19B H19C 106.8 . . ? C18 C19B H19C 106.8 . . ? C20B C19B H19D 106.8 . . ? C18 C19B H19D 106.8 . . ? H19C C19B H19D 106.7 . . ? C19B C20B H20D 109.5 . . ? C19B C20B H20E 109.5 . . ? H20D C20B H20E 109.5 . . ? C19B C20B H20F 109.5 . . ? H20D C20B H20F 109.5 . . ? H20E C20B H20F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Cu1 Cu2 O4 -6.25(16) . . . . ? N1 Cu1 Cu2 O4 -174.96(17) . . . . ? O1 Cu1 Cu2 O4 -179.20(16) . . . . ? O5 Cu1 Cu2 O4 100.81(14) 3_755 . . . ? O4 Cu1 Cu2 O5 -179.96(16) . . . . ? O2 Cu1 Cu2 O5 173.79(14) . . . . ? N1 Cu1 Cu2 O5 5.08(15) . . . . ? O1 Cu1 Cu2 O5 0.84(14) . . . . ? O5 Cu1 Cu2 O5 -79.15(12) 3_755 . . . ? O4 Cu1 Cu2 O1 179.20(16) . . . . ? O2 Cu1 Cu2 O1 172.95(14) . . . . ? N1 Cu1 Cu2 O1 4.24(15) . . . . ? O5 Cu1 Cu2 O1 -79.99(11) 3_755 . . . ? O4 Cu1 Cu2 N2 9.26(16) . . . . ? O2 Cu1 Cu2 N2 3.01(15) . . . . ? N1 Cu1 Cu2 N2 -165.70(15) . . . . ? O1 Cu1 Cu2 N2 -169.94(14) . . . . ? O5 Cu1 Cu2 N2 110.07(12) 3_755 . . . ? O4 Cu1 Cu2 O1 -103.35(14) . . . 3_755 ? O2 Cu1 Cu2 O1 -109.60(11) . . . 3_755 ? N1 Cu1 Cu2 O1 81.69(12) . . . 3_755 ? O1 Cu1 Cu2 O1 77.45(12) . . . 3_755 ? O5 Cu1 Cu2 O1 -2.54(7) 3_755 . . 3_755 ? O4 Cu1 O1 C7 139.5(2) . . . . ? O2 Cu1 O1 C7 96.1(8) . . . . ? N1 Cu1 O1 C7 -37.0(2) . . . . ? O5 Cu1 O1 C7 -125.8(2) 3_755 . . . ? Cu2 Cu1 O1 C7 140.0(3) . . . . ? O4 Cu1 O1 Cu2 -0.49(10) . . . . ? O2 Cu1 O1 Cu2 -43.9(8) . . . . ? N1 Cu1 O1 Cu2 -176.92(11) . . . . ? O5 Cu1 O1 Cu2 94.25(9) 3_755 . . . ? O4 Cu1 O1 Cu2 -99.14(10) . . . 3_755 ? O2 Cu1 O1 Cu2 -142.5(7) . . . 3_755 ? N1 Cu1 O1 Cu2 84.43(10) . . . 3_755 ? O5 Cu1 O1 Cu2 -4.40(7) 3_755 . . 3_755 ? Cu2 Cu1 O1 Cu2 -98.65(10) . . . 3_755 ? O4 Cu2 O1 C7 -136.7(2) . . . . ? O5 Cu2 O1 C7 43.4(2) . . . . ? N2 Cu2 O1 C7 -100.5(5) . . . . ? O1 Cu2 O1 C7 122.2(2) 3_755 . . . ? Cu1 Cu2 O1 C7 -137.2(3) . . . . ? O4 Cu2 O1 Cu1 0.50(10) . . . . ? O5 Cu2 O1 Cu1 -179.39(10) . . . . ? N2 Cu2 O1 Cu1 36.8(5) . . . . ? O1 Cu2 O1 Cu1 -100.55(10) 3_755 . . . ? O4 Cu2 O1 Cu2 101.04(10) . . . 3_755 ? O5 Cu2 O1 Cu2 -78.84(9) . . . 3_755 ? N2 Cu2 O1 Cu2 137.3(4) . . . 3_755 ? O1 Cu2 O1 Cu2 0.0 3_755 . . 3_755 ? Cu1 Cu2 O1 Cu2 100.55(10) . . . 3_755 ? O4 Cu1 O2 C8 -93.9(2) . . . . ? N1 Cu1 O2 C8 81.7(2) . . . . ? O1 Cu1 O2 C8 -51.4(8) . . . . ? O5 Cu1 O2 C8 171.7(2) 3_755 . . . ? Cu2 Cu1 O2 C8 -90.1(2) . . . . ? O5 Cu2 O4 C17 161.2(6) . . . . ? O1 Cu2 O4 C17 160.5(3) . . . . ? N2 Cu2 O4 C17 -11.8(3) . . . . ? O1 Cu2 O4 C17 -118.8(3) 3_755 . . . ? Cu1 Cu2 O4 C17 161.0(4) . . . . ? O5 Cu2 O4 Cu1 0.2(7) . . . . ? O1 Cu2 O4 Cu1 -0.53(11) . . . . ? N2 Cu2 O4 Cu1 -172.80(13) . . . . ? O1 Cu2 O4 Cu1 80.15(12) 3_755 . . . ? O2 Cu1 O4 C17 14.3(3) . . . . ? N1 Cu1 O4 C17 -139.8(6) . . . . ? O1 Cu1 O4 C17 -160.6(3) . . . . ? O5 Cu1 O4 C17 120.6(3) 3_755 . . . ? Cu2 Cu1 O4 C17 -161.1(4) . . . . ? O2 Cu1 O4 Cu2 175.44(12) . . . . ? N1 Cu1 O4 Cu2 21.3(7) . . . . ? O1 Cu1 O4 Cu2 0.53(11) . . . . ? O5 Cu1 O4 Cu2 -78.31(12) 3_755 . . . ? O4 Cu2 O5 C18 -85.6(7) . . . . ? O1 Cu2 O5 C18 -84.9(2) . . . . ? N2 Cu2 O5 C18 87.4(2) . . . . ? O1 Cu2 O5 C18 -167.1(2) 3_755 . . . ? Cu1 Cu2 O5 C18 -85.4(2) . . . . ? O4 Cu2 O5 Cu1 86.0(7) . . . 3_755 ? O1 Cu2 O5 Cu1 86.72(9) . . . 3_755 ? N2 Cu2 O5 Cu1 -101.04(11) . . . 3_755 ? O1 Cu2 O5 Cu1 4.50(8) 3_755 . . 3_755 ? Cu1 Cu2 O5 Cu1 86.18(10) . . . 3_755 ? O4 Cu1 N1 C1 -161.8(5) . . . . ? O2 Cu1 N1 C1 43.9(3) . . . . ? O1 Cu1 N1 C1 -141.5(3) . . . . ? O5 Cu1 N1 C1 -61.9(2) 3_755 . . . ? Cu2 Cu1 N1 C1 -144.3(2) . . . . ? O4 Cu1 N1 C5 16.2(7) . . . . ? O2 Cu1 N1 C5 -138.1(2) . . . . ? O1 Cu1 N1 C5 36.5(2) . . . . ? O5 Cu1 N1 C5 116.1(2) 3_755 . . . ? Cu2 Cu1 N1 C5 33.8(3) . . . . ? O4 Cu2 N2 C11 162.9(3) . . . . ? O5 Cu2 N2 C11 -16.0(3) . . . . ? O1 Cu2 N2 C11 127.6(4) . . . . ? O1 Cu2 N2 C11 -97.0(3) 3_755 . . . ? Cu1 Cu2 N2 C11 157.2(2) . . . . ? O4 Cu2 N2 C15 -14.6(3) . . . . ? O5 Cu2 N2 C15 166.5(3) . . . . ? O1 Cu2 N2 C15 -49.9(6) . . . . ? O1 Cu2 N2 C15 85.5(3) 3_755 . . . ? Cu1 Cu2 N2 C15 -20.2(3) . . . . ? C5 N1 C1 C2 -1.7(5) . . . . ? Cu1 N1 C1 C2 176.3(3) . . . . ? N1 C1 C2 C3 -0.6(5) . . . . ? C1 C2 C3 C4 1.9(6) . . . . ? C2 C3 C4 C5 -1.0(6) . . . . ? C1 N1 C5 C4 2.6(5) . . . . ? Cu1 N1 C5 C4 -175.4(3) . . . . ? C1 N1 C5 C6 -176.9(3) . . . . ? Cu1 N1 C5 C6 5.0(4) . . . . ? C3 C4 C5 N1 -1.3(5) . . . . ? C3 C4 C5 C6 178.3(3) . . . . ? N1 C5 C6 C7 -63.8(4) . . . . ? C4 C5 C6 C7 116.6(4) . . . . ? Cu1 O1 C7 C6 -3.5(4) . . . . ? Cu2 O1 C7 C6 125.6(3) . . . . ? Cu2 O1 C7 C6 -118.8(3) 3_755 . . . ? C5 C6 C7 O1 61.1(4) . . . . ? Cu1 O2 C8 O3 -0.7(4) . . . . ? Cu1 O2 C8 C9 177.7(3) . . . . ? O3 C8 C9 C10 -5.7(6) . . . . ? O2 C8 C9 C10 175.9(4) . . . . ? C15 N2 C11 C12 -1.2(5) . . . . ? Cu2 N2 C11 C12 -178.9(3) . . . . ? N2 C11 C12 C13 0.2(6) . . . . ? C11 C12 C13 C14 1.0(6) . . . . ? C12 C13 C14 C15 -1.0(6) . . . . ? C11 N2 C15 C14 1.1(5) . . . . ? Cu2 N2 C15 C14 178.6(3) . . . . ? C11 N2 C15 C16 -178.2(3) . . . . ? Cu2 N2 C15 C16 -0.7(5) . . . . ? C13 C14 C15 N2 0.0(6) . . . . ? C13 C14 C15 C16 179.3(4) . . . . ? N2 C15 C16 C17 43.9(5) . . . . ? C14 C15 C16 C17 -135.4(3) . . . . ? Cu2 O4 C17 C16 50.8(4) . . . . ? Cu1 O4 C17 C16 -151.9(2) . . . . ? C15 C16 C17 O4 -68.9(4) . . . . ? Cu2 O5 C18 O6 -15.6(4) . . . . ? Cu1 O5 C18 O6 176.9(2) 3_755 . . . ? Cu2 O5 C18 C19B 161.1(14) . . . . ? Cu1 O5 C18 C19B -6.4(15) 3_755 . . . ? Cu2 O5 C18 C19A 168.3(14) . . . . ? Cu1 O5 C18 C19A 0.8(15) 3_755 . . . ? O6 C18 C19A C20A 11(3) . . . . ? O5 C18 C19A C20A -173(2) . . . . ? C19B C18 C19A C20A -119(18) . . . . ? O6 C18 C19B C20B 87(3) . . . . ? O5 C18 C19B C20B -89(2) . . . . ? C19A C18 C19B C20B 141(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C13 H13 O3 0.95 2.35 3.121(5) 137.4 2_745 C14 H14 O6 0.95 2.43 3.317(4) 154.4 2_745 C4 H4 O6 0.95 2.68 3.357(5) 129.1 3_765 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.655 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.086 #===END data_4-VAPOR _database_code_depnum_ccdc_archive 'CCDC 737396' #TrackingRef 'ALL-REVISEDR3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H52 Cu4 N4 O12' _chemical_formula_weight 1035.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 11.698(3) _cell_length_b 9.561(2) _cell_length_c 18.893(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.56(2) _cell_angle_gamma 90.00 _cell_volume 2099.2(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1476 _cell_measurement_theta_min 2.8972 _cell_measurement_theta_max 32.3412 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.637 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 2.066 _exptl_absorpt_correction_T_min 0.5955 _exptl_absorpt_correction_T_max 0.6593 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19269 _diffrn_reflns_av_R_equivalents 0.1298 _diffrn_reflns_av_sigmaI/netI 0.1731 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4822 _reflns_number_gt 2356 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0146P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4822 _refine_ls_number_parameters 293 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.1069 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.0622 _refine_ls_wR_factor_gt 0.0552 _refine_ls_goodness_of_fit_ref 0.712 _refine_ls_restrained_S_all 0.710 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.28227(4) 0.09908(5) 0.46193(2) 0.02242(13) Uani 1 1 d . . . Cu2 Cu 0.52248(4) 0.05765(5) 0.41960(2) 0.02070(13) Uani 1 1 d . . . O1 O 0.4438(2) 0.1378(2) 0.49961(12) 0.0188(6) Uani 1 1 d . . . O2 O 0.1270(2) 0.0672(3) 0.41322(12) 0.0245(6) Uani 1 1 d . . . O3 O 0.1568(3) 0.2871(3) 0.38333(14) 0.0394(8) Uani 1 1 d . . . O4 O 0.3641(2) 0.0264(2) 0.38811(12) 0.0265(7) Uani 1 1 d . . . O5 O 0.6761(2) 0.1026(2) 0.46479(11) 0.0199(6) Uani 1 1 d . . . O6 O 0.6784(3) 0.3081(2) 0.41097(13) 0.0340(8) Uani 1 1 d . A . N1 N 0.2215(3) 0.1927(3) 0.54253(16) 0.0208(7) Uani 1 1 d . . . N2 N 0.5704(3) -0.0057(3) 0.32349(15) 0.0214(8) Uani 1 1 d . . . C1 C 0.1311(3) 0.1417(4) 0.57074(19) 0.0232(10) Uani 1 1 d . . . H1 H 0.0928 0.0622 0.5492 0.028 Uiso 1 1 calc R . . C2 C 0.0906(4) 0.1993(4) 0.6299(2) 0.0316(11) Uani 1 1 d . . . H2 H 0.0261 0.1605 0.6492 0.038 Uiso 1 1 calc R . . C3 C 0.1460(4) 0.3136(4) 0.6598(2) 0.0366(12) Uani 1 1 d . . . H3 H 0.1211 0.3547 0.7012 0.044 Uiso 1 1 calc R . . C4 C 0.2383(4) 0.3700(4) 0.6303(2) 0.0326(11) Uani 1 1 d . . . H4 H 0.2762 0.4508 0.6507 0.039 Uiso 1 1 calc R . . C5 C 0.2748(4) 0.3079(4) 0.57116(19) 0.0227(10) Uani 1 1 d . . . C6 C 0.3724(3) 0.3649(3) 0.53429(19) 0.0242(10) Uani 1 1 d . . . H6A H 0.3991 0.4535 0.5578 0.029 Uiso 1 1 calc R . . H6B H 0.3430 0.3870 0.4843 0.029 Uiso 1 1 calc R . . C7 C 0.4748(4) 0.2674(3) 0.5341(2) 0.0274(10) Uani 1 1 d . . . H7A H 0.5348 0.3136 0.5094 0.033 Uiso 1 1 calc R . . H7B H 0.5077 0.2488 0.5839 0.033 Uiso 1 1 calc R . . C8 C 0.0966(4) 0.1821(4) 0.3807(2) 0.0267(10) Uani 1 1 d . . . C9 C -0.0199(4) 0.1798(4) 0.3376(2) 0.0361(11) Uani 1 1 d . . . H9A H -0.0184 0.1101 0.2989 0.043 Uiso 1 1 calc R . . H9B H -0.0774 0.1478 0.3687 0.043 Uiso 1 1 calc R . . C10 C -0.0590(4) 0.3175(4) 0.3050(2) 0.0586(15) Uani 1 1 d . . . H10A H -0.0704 0.3844 0.3428 0.088 Uiso 1 1 calc R . . H10B H -0.1317 0.3044 0.2744 0.088 Uiso 1 1 calc R . . H10C H -0.0005 0.3534 0.2765 0.088 Uiso 1 1 calc R . . C11 C 0.6762(4) 0.0272(4) 0.30890(19) 0.0258(10) Uani 1 1 d . . . H11 H 0.7249 0.0768 0.3440 0.031 Uiso 1 1 calc R . . C12 C 0.7192(4) -0.0064(4) 0.2462(2) 0.0329(11) Uani 1 1 d . . . H12 H 0.7949 0.0204 0.2382 0.039 Uiso 1 1 calc R . . C13 C 0.6498(4) -0.0796(4) 0.1958(2) 0.0360(11) Uani 1 1 d . . . H13 H 0.6771 -0.1064 0.1523 0.043 Uiso 1 1 calc R . . C14 C 0.5411(4) -0.1134(4) 0.20888(19) 0.0312(11) Uani 1 1 d . . . H14 H 0.4916 -0.1621 0.1738 0.037 Uiso 1 1 calc R . . C15 C 0.5019(4) -0.0772(4) 0.27317(18) 0.0239(9) Uani 1 1 d . . . C16 C 0.3820(4) -0.1140(4) 0.28510(18) 0.0281(10) Uani 1 1 d . . . H16A H 0.3843 -0.1969 0.3166 0.034 Uiso 1 1 calc R . . H16B H 0.3390 -0.1405 0.2389 0.034 Uiso 1 1 calc R . . C17 C 0.3176(3) 0.0010(4) 0.31767(18) 0.0265(10) Uani 1 1 d . . . H17A H 0.3216 0.0875 0.2893 0.032 Uiso 1 1 calc R . . H17B H 0.2357 -0.0257 0.3167 0.032 Uiso 1 1 calc R . . C18 C 0.7176(4) 0.2264(4) 0.4566(2) 0.0231(10) Uani 1 1 d U . . C19A C 0.820(2) 0.266(2) 0.4988(11) 0.037(5) Uani 0.509(7) 1 d PU A 1 H19A H 0.8058 0.2381 0.5475 0.044 Uiso 0.509(7) 1 calc PR A 1 H19B H 0.8774 0.1988 0.4847 0.044 Uiso 0.509(7) 1 calc PR A 1 C20A C 0.8823(9) 0.3895(9) 0.5098(5) 0.067(4) Uani 0.509(7) 1 d PU A 1 H20A H 0.9199 0.4111 0.4674 0.100 Uiso 0.509(7) 1 calc PR A 1 H20B H 0.9408 0.3783 0.5509 0.100 Uiso 0.509(7) 1 calc PR A 1 H20C H 0.8303 0.4661 0.5190 0.100 Uiso 0.509(7) 1 calc PR A 1 C19B C 0.827(2) 0.257(3) 0.5175(12) 0.037(4) Uani 0.491(7) 1 d PU A 2 H19C H 0.8656 0.1674 0.5317 0.045 Uiso 0.491(7) 1 calc PR A 2 H19D H 0.8839 0.3170 0.4966 0.045 Uiso 0.491(7) 1 calc PR A 2 C20B C 0.7966(9) 0.3175(10) 0.5731(5) 0.049(3) Uani 0.491(7) 1 d PU A 2 H20D H 0.7413 0.3920 0.5585 0.074 Uiso 0.491(7) 1 calc PR A 2 H20E H 0.8644 0.3579 0.6010 0.074 Uiso 0.491(7) 1 calc PR A 2 H20F H 0.7608 0.2488 0.6021 0.074 Uiso 0.491(7) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0202(3) 0.0240(3) 0.0227(3) -0.0024(2) 0.0006(2) 0.0012(3) Cu2 0.0204(3) 0.0218(3) 0.0193(2) -0.0017(2) -0.0002(2) 0.0004(3) O1 0.0211(16) 0.0164(13) 0.0182(13) -0.0056(11) -0.0010(13) 0.0029(14) O2 0.0211(17) 0.0275(15) 0.0240(14) -0.0033(13) -0.0010(13) -0.0016(15) O3 0.033(2) 0.0425(18) 0.0417(18) 0.0112(15) -0.0003(16) -0.0083(18) O4 0.0217(17) 0.0408(16) 0.0153(13) -0.0098(12) -0.0047(13) -0.0005(15) O5 0.0185(15) 0.0212(13) 0.0189(13) -0.0018(11) -0.0025(12) -0.0013(15) O6 0.046(2) 0.0219(15) 0.0335(17) 0.0060(13) 0.0018(16) 0.0034(17) N1 0.0182(19) 0.0174(16) 0.0260(18) 0.0023(15) -0.0005(16) 0.0049(18) N2 0.022(2) 0.0213(17) 0.0201(18) -0.0010(14) -0.0020(16) 0.0042(18) C1 0.021(3) 0.021(2) 0.027(2) 0.0005(17) 0.000(2) 0.000(2) C2 0.032(3) 0.029(2) 0.036(3) 0.008(2) 0.015(2) 0.000(2) C3 0.049(3) 0.037(3) 0.027(2) -0.004(2) 0.018(2) 0.001(3) C4 0.043(3) 0.023(2) 0.032(2) -0.0072(19) 0.009(2) 0.001(2) C5 0.028(3) 0.018(2) 0.021(2) 0.0020(17) 0.000(2) 0.000(2) C6 0.031(3) 0.016(2) 0.026(2) 0.0025(16) 0.007(2) 0.002(2) C7 0.026(3) 0.019(2) 0.037(2) -0.0048(18) 0.000(2) -0.006(2) C8 0.022(3) 0.033(3) 0.027(2) 0.000(2) 0.010(2) 0.000(2) C9 0.024(3) 0.049(3) 0.035(3) 0.009(2) 0.001(2) 0.009(3) C10 0.053(4) 0.061(3) 0.061(3) 0.019(3) 0.003(3) 0.010(3) C11 0.024(3) 0.032(2) 0.021(2) -0.0067(18) 0.001(2) -0.002(2) C12 0.023(3) 0.045(3) 0.030(2) -0.004(2) 0.005(2) 0.003(2) C13 0.035(3) 0.052(3) 0.022(2) -0.005(2) 0.006(2) 0.014(3) C14 0.031(3) 0.039(2) 0.023(2) -0.0114(19) 0.000(2) 0.004(3) C15 0.029(2) 0.017(2) 0.024(2) -0.0059(17) -0.002(2) 0.008(2) C16 0.032(3) 0.029(2) 0.020(2) -0.0031(17) -0.007(2) -0.003(2) C17 0.017(2) 0.034(2) 0.027(2) -0.0013(18) -0.005(2) 0.000(2) C18 0.022(3) 0.022(2) 0.026(2) -0.0109(18) 0.002(2) -0.004(2) C19A 0.042(8) 0.038(8) 0.026(10) -0.012(7) -0.013(6) 0.012(6) C20A 0.064(8) 0.034(5) 0.096(9) 0.016(6) -0.018(7) 0.001(6) C19B 0.033(9) 0.043(8) 0.032(10) 0.001(6) -0.011(6) -0.032(7) C20B 0.046(7) 0.065(7) 0.031(6) -0.013(5) -0.020(5) -0.007(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 1.910(2) . ? Cu1 O2 1.964(3) . ? Cu1 N1 1.968(3) . ? Cu1 O1 1.976(3) . ? Cu1 O5 2.391(2) 3_656 ? Cu1 Cu2 3.0342(10) . ? Cu2 O4 1.904(3) . ? Cu2 O5 1.947(3) . ? Cu2 O1 2.010(2) . ? Cu2 N2 2.052(3) . ? Cu2 O1 2.417(2) 3_656 ? O1 C7 1.427(4) . ? O1 Cu2 2.417(2) 3_656 ? O2 C8 1.289(4) . ? O3 C8 1.224(4) . ? O4 C17 1.400(4) . ? O5 C18 1.296(4) . ? O5 Cu1 2.391(2) 3_656 ? O6 C18 1.214(4) . ? N1 C1 1.330(5) . ? N1 C5 1.348(4) . ? N2 C11 1.337(5) . ? N2 C15 1.356(4) . ? C1 C2 1.377(5) . ? C1 H1 0.9500 . ? C2 C3 1.360(5) . ? C2 H2 0.9500 . ? C3 C4 1.380(5) . ? C3 H3 0.9500 . ? C4 C5 1.376(5) . ? C4 H4 0.9500 . ? C5 C6 1.506(5) . ? C6 C7 1.517(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.506(6) . ? C9 C10 1.502(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.376(5) . ? C11 H11 0.9500 . ? C12 C13 1.372(5) . ? C12 H12 0.9500 . ? C13 C14 1.362(5) . ? C13 H13 0.9500 . ? C14 C15 1.390(4) . ? C14 H14 0.9500 . ? C15 C16 1.488(5) . ? C16 C17 1.504(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19A 1.41(2) . ? C18 C19B 1.65(2) . ? C19A C20A 1.39(2) . ? C19A H19A 0.9900 . ? C19A H19B 0.9900 . ? C20A H20A 0.9800 . ? C20A H20B 0.9800 . ? C20A H20C 0.9800 . ? C19B C20B 1.29(2) . ? C19B H19C 0.9900 . ? C19B H19D 0.9900 . ? C20B H20D 0.9800 . ? C20B H20E 0.9800 . ? C20B H20F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cu1 O2 96.62(11) . . ? O4 Cu1 N1 170.34(13) . . ? O2 Cu1 N1 92.09(12) . . ? O4 Cu1 O1 78.05(10) . . ? O2 Cu1 O1 173.10(10) . . ? N1 Cu1 O1 92.93(12) . . ? O4 Cu1 O5 92.50(9) . 3_656 ? O2 Cu1 O5 105.21(10) . 3_656 ? N1 Cu1 O5 89.22(10) . 3_656 ? O1 Cu1 O5 79.60(9) . 3_656 ? O4 Cu1 Cu2 37.21(8) . . ? O2 Cu1 Cu2 133.72(7) . . ? N1 Cu1 Cu2 133.69(10) . . ? O1 Cu1 Cu2 40.84(6) . . ? O5 Cu1 Cu2 85.07(6) 3_656 . ? O4 Cu2 O5 171.14(10) . . ? O4 Cu2 O1 77.39(10) . . ? O5 Cu2 O1 93.75(10) . . ? O4 Cu2 N2 91.81(12) . . ? O5 Cu2 N2 96.97(12) . . ? O1 Cu2 N2 166.69(11) . . ? O4 Cu2 O1 99.15(10) . 3_656 ? O5 Cu2 O1 79.49(9) . 3_656 ? O1 Cu2 O1 82.86(9) . 3_656 ? N2 Cu2 O1 106.82(9) . 3_656 ? O4 Cu2 Cu1 37.37(7) . . ? O5 Cu2 Cu1 133.77(7) . . ? O1 Cu2 Cu1 40.02(7) . . ? N2 Cu2 Cu1 128.80(10) . . ? O1 Cu2 Cu1 91.37(6) 3_656 . ? C7 O1 Cu1 120.7(2) . . ? C7 O1 Cu2 124.1(2) . . ? Cu1 O1 Cu2 99.15(10) . . ? C7 O1 Cu2 111.6(2) . 3_656 ? Cu1 O1 Cu2 99.39(9) . 3_656 ? Cu2 O1 Cu2 97.14(9) . 3_656 ? C8 O2 Cu1 106.3(3) . . ? C17 O4 Cu2 125.6(2) . . ? C17 O4 Cu1 125.8(2) . . ? Cu2 O4 Cu1 105.41(11) . . ? C18 O5 Cu2 119.2(3) . . ? C18 O5 Cu1 138.8(3) . 3_656 ? Cu2 O5 Cu1 101.11(10) . 3_656 ? C1 N1 C5 119.4(3) . . ? C1 N1 Cu1 121.2(3) . . ? C5 N1 Cu1 119.4(3) . . ? C11 N2 C15 117.4(3) . . ? C11 N2 Cu2 117.8(3) . . ? C15 N2 Cu2 124.8(3) . . ? N1 C1 C2 122.7(4) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 117.9(4) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C2 C3 C4 120.2(4) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 119.3(4) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? N1 C5 C4 120.4(4) . . ? N1 C5 C6 116.8(3) . . ? C4 C5 C6 122.8(4) . . ? C5 C6 C7 114.8(3) . . ? C5 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? C5 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? O1 C7 C6 112.0(3) . . ? O1 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? O1 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? O3 C8 O2 123.6(4) . . ? O3 C8 C9 121.0(4) . . ? O2 C8 C9 115.4(4) . . ? C10 C9 C8 115.0(4) . . ? C10 C9 H9A 108.5 . . ? C8 C9 H9A 108.5 . . ? C10 C9 H9B 108.5 . . ? C8 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 C12 124.1(4) . . ? N2 C11 H11 117.9 . . ? C12 C11 H11 117.9 . . ? C13 C12 C11 118.1(4) . . ? C13 C12 H12 121.0 . . ? C11 C12 H12 121.0 . . ? C14 C13 C12 119.1(4) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C13 C14 C15 120.5(4) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? N2 C15 C14 120.8(4) . . ? N2 C15 C16 120.3(3) . . ? C14 C15 C16 118.9(4) . . ? C15 C16 C17 114.4(3) . . ? C15 C16 H16A 108.6 . . ? C17 C16 H16A 108.6 . . ? C15 C16 H16B 108.6 . . ? C17 C16 H16B 108.6 . . ? H16A C16 H16B 107.6 . . ? O4 C17 C16 111.0(3) . . ? O4 C17 H17A 109.4 . . ? C16 C17 H17A 109.4 . . ? O4 C17 H17B 109.4 . . ? C16 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? O6 C18 O5 123.8(4) . . ? O6 C18 C19A 117.0(10) . . ? O5 C18 C19A 118.9(10) . . ? O6 C18 C19B 125.6(10) . . ? O5 C18 C19B 110.6(10) . . ? C19A C18 C19B 10.4(17) . . ? C20A C19A C18 135.3(18) . . ? C20A C19A H19A 103.4 . . ? C18 C19A H19A 103.4 . . ? C20A C19A H19B 103.4 . . ? C18 C19A H19B 103.4 . . ? H19A C19A H19B 105.2 . . ? C20B C19B C18 112.4(17) . . ? C20B C19B H19C 109.1 . . ? C18 C19B H19C 109.1 . . ? C20B C19B H19D 109.1 . . ? C18 C19B H19D 109.1 . . ? H19C C19B H19D 107.8 . . ? C19B C20B H20D 109.5 . . ? C19B C20B H20E 109.5 . . ? H20D C20B H20E 109.5 . . ? C19B C20B H20F 109.5 . . ? H20D C20B H20F 109.5 . . ? H20E C20B H20F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Cu1 Cu2 O4 -5.64(16) . . . . ? N1 Cu1 Cu2 O4 -175.10(17) . . . . ? O1 Cu1 Cu2 O4 -179.48(17) . . . . ? O5 Cu1 Cu2 O4 100.72(13) 3_656 . . . ? O4 Cu1 Cu2 O5 179.95(16) . . . . ? O2 Cu1 Cu2 O5 174.30(14) . . . . ? N1 Cu1 Cu2 O5 4.85(15) . . . . ? O1 Cu1 Cu2 O5 0.47(14) . . . . ? O5 Cu1 Cu2 O5 -79.33(12) 3_656 . . . ? O4 Cu1 Cu2 O1 179.48(17) . . . . ? O2 Cu1 Cu2 O1 173.84(15) . . . . ? N1 Cu1 Cu2 O1 4.38(15) . . . . ? O5 Cu1 Cu2 O1 -79.80(11) 3_656 . . . ? O4 Cu1 Cu2 N2 9.66(16) . . . . ? O2 Cu1 Cu2 N2 4.01(14) . . . . ? N1 Cu1 Cu2 N2 -165.44(15) . . . . ? O1 Cu1 Cu2 N2 -169.82(14) . . . . ? O5 Cu1 Cu2 N2 110.38(12) 3_656 . . . ? O4 Cu1 Cu2 O1 -103.34(13) . . . 3_656 ? O2 Cu1 Cu2 O1 -108.98(12) . . . 3_656 ? N1 Cu1 Cu2 O1 81.56(13) . . . 3_656 ? O1 Cu1 Cu2 O1 77.18(12) . . . 3_656 ? O5 Cu1 Cu2 O1 -2.62(8) 3_656 . . 3_656 ? O4 Cu1 O1 C7 138.7(2) . . . . ? O2 Cu1 O1 C7 98.8(9) . . . . ? N1 Cu1 O1 C7 -37.8(2) . . . . ? O5 Cu1 O1 C7 -126.5(2) 3_656 . . . ? Cu2 Cu1 O1 C7 139.0(3) . . . . ? O4 Cu1 O1 Cu2 -0.32(10) . . . . ? O2 Cu1 O1 Cu2 -40.2(9) . . . . ? N1 Cu1 O1 Cu2 -176.83(11) . . . . ? O5 Cu1 O1 Cu2 94.51(9) 3_656 . . . ? O4 Cu1 O1 Cu2 -99.20(10) . . . 3_656 ? O2 Cu1 O1 Cu2 -139.1(8) . . . 3_656 ? N1 Cu1 O1 Cu2 84.30(10) . . . 3_656 ? O5 Cu1 O1 Cu2 -4.37(8) 3_656 . . 3_656 ? Cu2 Cu1 O1 Cu2 -98.87(10) . . . 3_656 ? O4 Cu2 O1 C7 -136.8(3) . . . . ? O5 Cu2 O1 C7 43.3(3) . . . . ? N2 Cu2 O1 C7 -100.4(5) . . . . ? O1 Cu2 O1 C7 122.2(3) 3_656 . . . ? Cu1 Cu2 O1 C7 -137.1(3) . . . . ? O4 Cu2 O1 Cu1 0.32(10) . . . . ? O5 Cu2 O1 Cu1 -179.66(10) . . . . ? N2 Cu2 O1 Cu1 36.7(5) . . . . ? O1 Cu2 O1 Cu1 -100.76(11) 3_656 . . . ? O4 Cu2 O1 Cu2 101.08(10) . . . 3_656 ? O5 Cu2 O1 Cu2 -78.91(10) . . . 3_656 ? N2 Cu2 O1 Cu2 137.5(4) . . . 3_656 ? O1 Cu2 O1 Cu2 0.0 3_656 . . 3_656 ? Cu1 Cu2 O1 Cu2 100.76(11) . . . 3_656 ? O4 Cu1 O2 C8 -93.8(2) . . . . ? N1 Cu1 O2 C8 82.0(2) . . . . ? O1 Cu1 O2 C8 -54.6(9) . . . . ? O5 Cu1 O2 C8 171.8(2) 3_656 . . . ? Cu2 Cu1 O2 C8 -90.4(2) . . . . ? O5 Cu2 O4 C17 160.4(6) . . . . ? O1 Cu2 O4 C17 160.3(3) . . . . ? N2 Cu2 O4 C17 -11.8(3) . . . . ? O1 Cu2 O4 C17 -119.2(3) 3_656 . . . ? Cu1 Cu2 O4 C17 160.7(3) . . . . ? O5 Cu2 O4 Cu1 -0.3(8) . . . . ? O1 Cu2 O4 Cu1 -0.34(11) . . . . ? N2 Cu2 O4 Cu1 -172.49(12) . . . . ? O1 Cu2 O4 Cu1 80.15(11) 3_656 . . . ? O2 Cu1 O4 C17 15.3(3) . . . . ? N1 Cu1 O4 C17 -139.0(6) . . . . ? O1 Cu1 O4 C17 -160.3(3) . . . . ? O5 Cu1 O4 C17 120.9(3) 3_656 . . . ? Cu2 Cu1 O4 C17 -160.6(3) . . . . ? O2 Cu1 O4 Cu2 175.90(11) . . . . ? N1 Cu1 O4 Cu2 21.6(7) . . . . ? O1 Cu1 O4 Cu2 0.35(11) . . . . ? O5 Cu1 O4 Cu2 -78.47(12) 3_656 . . . ? O4 Cu2 O5 C18 -84.7(7) . . . . ? O1 Cu2 O5 C18 -84.7(2) . . . . ? N2 Cu2 O5 C18 87.4(2) . . . . ? O1 Cu2 O5 C18 -166.7(2) 3_656 . . . ? Cu1 Cu2 O5 C18 -85.0(2) . . . . ? O4 Cu2 O5 Cu1 86.4(7) . . . 3_656 ? O1 Cu2 O5 Cu1 86.47(9) . . . 3_656 ? N2 Cu2 O5 Cu1 -101.44(10) . . . 3_656 ? O1 Cu2 O5 Cu1 4.46(8) 3_656 . . 3_656 ? Cu1 Cu2 O5 Cu1 86.17(10) . . . 3_656 ? O4 Cu1 N1 C1 -162.3(6) . . . . ? O2 Cu1 N1 C1 43.2(3) . . . . ? O1 Cu1 N1 C1 -141.5(3) . . . . ? O5 Cu1 N1 C1 -62.0(3) 3_656 . . . ? Cu2 Cu1 N1 C1 -144.4(2) . . . . ? O4 Cu1 N1 C5 15.4(8) . . . . ? O2 Cu1 N1 C5 -139.1(3) . . . . ? O1 Cu1 N1 C5 36.2(3) . . . . ? O5 Cu1 N1 C5 115.8(3) 3_656 . . . ? Cu2 Cu1 N1 C5 33.3(3) . . . . ? O4 Cu2 N2 C11 163.9(3) . . . . ? O5 Cu2 N2 C11 -14.9(3) . . . . ? O1 Cu2 N2 C11 128.5(5) . . . . ? O1 Cu2 N2 C11 -96.0(3) 3_656 . . . ? Cu1 Cu2 N2 C11 158.0(2) . . . . ? O4 Cu2 N2 C15 -15.3(3) . . . . ? O5 Cu2 N2 C15 165.9(3) . . . . ? O1 Cu2 N2 C15 -50.7(6) . . . . ? O1 Cu2 N2 C15 84.8(3) 3_656 . . . ? Cu1 Cu2 N2 C15 -21.2(3) . . . . ? C5 N1 C1 C2 -1.9(6) . . . . ? Cu1 N1 C1 C2 175.8(3) . . . . ? N1 C1 C2 C3 0.4(6) . . . . ? C1 C2 C3 C4 1.1(6) . . . . ? C2 C3 C4 C5 -1.2(6) . . . . ? C1 N1 C5 C4 1.9(5) . . . . ? Cu1 N1 C5 C4 -175.9(3) . . . . ? C1 N1 C5 C6 -176.7(3) . . . . ? Cu1 N1 C5 C6 5.5(4) . . . . ? C3 C4 C5 N1 -0.4(6) . . . . ? C3 C4 C5 C6 178.1(4) . . . . ? N1 C5 C6 C7 -63.5(4) . . . . ? C4 C5 C6 C7 118.0(4) . . . . ? Cu1 O1 C7 C6 -2.2(4) . . . . ? Cu2 O1 C7 C6 126.4(3) . . . . ? Cu2 O1 C7 C6 -118.2(3) 3_656 . . . ? C5 C6 C7 O1 59.6(4) . . . . ? Cu1 O2 C8 O3 -1.2(4) . . . . ? Cu1 O2 C8 C9 178.3(3) . . . . ? O3 C8 C9 C10 -5.5(6) . . . . ? O2 C8 C9 C10 175.0(3) . . . . ? C15 N2 C11 C12 0.4(6) . . . . ? Cu2 N2 C11 C12 -178.9(3) . . . . ? N2 C11 C12 C13 -0.8(6) . . . . ? C11 C12 C13 C14 1.4(6) . . . . ? C12 C13 C14 C15 -1.5(6) . . . . ? C11 N2 C15 C14 -0.5(5) . . . . ? Cu2 N2 C15 C14 178.7(3) . . . . ? C11 N2 C15 C16 -178.5(3) . . . . ? Cu2 N2 C15 C16 0.7(5) . . . . ? C13 C14 C15 N2 1.1(6) . . . . ? C13 C14 C15 C16 179.1(4) . . . . ? N2 C15 C16 C17 42.3(5) . . . . ? C14 C15 C16 C17 -135.7(4) . . . . ? Cu2 O4 C17 C16 50.7(4) . . . . ? Cu1 O4 C17 C16 -152.5(2) . . . . ? C15 C16 C17 O4 -68.2(4) . . . . ? Cu2 O5 C18 O6 -16.2(5) . . . . ? Cu1 O5 C18 O6 177.1(2) 3_656 . . . ? Cu2 O5 C18 C19A 169.4(11) . . . . ? Cu1 O5 C18 C19A 2.7(12) 3_656 . . . ? Cu2 O5 C18 C19B 162.5(10) . . . . ? Cu1 O5 C18 C19B -4.2(10) 3_656 . . . ? O6 C18 C19A C20A 12(3) . . . . ? O5 C18 C19A C20A -172.8(19) . . . . ? C19B C18 C19A C20A -135(12) . . . . ? O6 C18 C19B C20B 86.3(18) . . . . ? O5 C18 C19B C20B -92.4(19) . . . . ? C19A C18 C19B C20B 123(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C13 H13 O3 0.95 2.36 3.122(5) 137.2 2_645 C14 H14 O6 0.95 2.42 3.310(5) 155.0 2_645 C4 H4 O6 0.95 2.66 3.348(5) 129.4 3_666 C6 H6A O6 0.99 2.55 3.368(4) 140.1 3_666 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.466 _refine_diff_density_min -0.484 _refine_diff_density_rms 0.094 #===END data_1c _database_code_depnum_ccdc_archive 'CCDC 747411' #TrackingRef 'ALL-REVISEDR3.cif'.2H2O #TrackingRef 'ALL-REVISEDR3.cif'REGENERATED _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H15 Cu N O5' _chemical_formula_weight 280.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3200 1.2650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.900(3) _cell_length_b 8.684(3) _cell_length_c 10.058(4) _cell_angle_alpha 71.77(3) _cell_angle_beta 78.27(3) _cell_angle_gamma 69.51(3) _cell_volume 610.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 992 _cell_measurement_theta_min 3.1606 _cell_measurement_theta_max 32.3096 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 290 _exptl_absorpt_coefficient_mu 1.794 _exptl_absorpt_correction_T_min 0.5891 _exptl_absorpt_correction_T_max 0.7045 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5298 _diffrn_reflns_av_R_equivalents 0.1173 _diffrn_reflns_av_sigmaI/netI 0.1113 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2145 _reflns_number_gt 1446 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.1452P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2145 _refine_ls_number_parameters 162 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.1070 _refine_ls_R_factor_gt 0.0715 _refine_ls_wR_factor_ref 0.2349 _refine_ls_wR_factor_gt 0.1986 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.003 _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 0.32352(13) 0.05300(12) 0.08826(10) 0.0396(4) Uani 1 1 d . . . O1 O 0.4382(8) 0.1075(7) -0.0979(6) 0.0508(16) Uani 1 1 d . . . O2 O 0.2454(8) -0.0143(7) 0.2881(6) 0.0464(14) Uani 1 1 d . . . O3 O 0.3597(10) 0.1903(9) 0.2671(7) 0.0633(18) Uani 1 1 d . . . N1 N 0.0758(8) 0.1897(8) 0.0347(7) 0.0380(16) Uani 1 1 d . . . C1 C -0.0652(12) 0.1376(12) 0.1073(12) 0.059(3) Uani 1 1 d . . . H1 H -0.0431 0.0452 0.1894 0.071 Uiso 1 1 calc R . . C2 C -0.2423(12) 0.2100(12) 0.0702(12) 0.057(3) Uani 1 1 d . . . H2 H -0.3400 0.1740 0.1278 0.068 Uiso 1 1 calc R . . C3 C -0.2685(14) 0.3343(14) -0.0522(12) 0.066(3) Uani 1 1 d . . . H3 H -0.3862 0.3842 -0.0834 0.080 Uiso 1 1 calc R . . C4 C -0.1253(13) 0.3895(13) -0.1325(11) 0.060(3) Uani 1 1 d . . . H4 H -0.1443 0.4744 -0.2194 0.072 Uiso 1 1 calc R . . C5 C 0.0459(12) 0.3199(10) -0.0850(10) 0.044(2) Uani 1 1 d . . . C6 C 0.2035(12) 0.3766(11) -0.1663(10) 0.053(2) Uani 1 1 d . . . H6A H 0.2505 0.4214 -0.1071 0.063 Uiso 1 1 calc R . . H6B H 0.1618 0.4706 -0.2501 0.063 Uiso 1 1 calc R . . C7 C 0.3555(12) 0.2348(11) -0.2132(9) 0.049(2) Uani 1 1 d . . . H7A H 0.3065 0.1831 -0.2655 0.059 Uiso 1 1 calc R . . H7B H 0.4480 0.2825 -0.2778 0.059 Uiso 1 1 calc R . . C8 C 0.2776(12) 0.0847(11) 0.3472(9) 0.045(2) Uani 1 1 d . . . C9 C 0.2323(15) 0.0634(14) 0.4956(11) 0.067(3) Uani 1 1 d . . . H9A H 0.3425 0.0358 0.5401 0.101 Uiso 1 1 calc R . . H9B H 0.1784 -0.0295 0.5352 0.101 Uiso 1 1 calc R . . H9C H 0.1449 0.1692 0.5132 0.101 Uiso 1 1 calc R . . O111 O 0.4736(15) 0.4055(12) 0.3595(13) 0.094(3) Uani 1 1 d U . . O222 O 0.2422(13) 0.6587(12) 0.4810(10) 0.081(3) Uani 1 1 d U . . H333 H 0.221(15) 0.777(17) 0.406(13) 0.09(2) Uiso 1 1 d U . . H444 H 0.189(18) 0.679(18) 0.541(14) 0.07(2) Uiso 1 1 d U . . H111 H 0.471(19) 0.340(18) 0.335(15) 0.09(2) Uiso 1 1 d U . . H222 H 0.397(18) 0.49(2) 0.408(15) 0.11(2) Uiso 1 1 d U . . 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 0.0403(6) 0.0442(6) 0.0375(7) -0.0064(4) -0.0128(4) -0.0160(4) O1 0.050(4) 0.049(3) 0.048(4) 0.005(3) -0.025(3) -0.014(3) O2 0.047(3) 0.049(3) 0.049(4) -0.020(3) -0.011(3) -0.013(3) O3 0.076(5) 0.068(4) 0.058(5) -0.016(3) -0.007(3) -0.038(4) N1 0.036(4) 0.047(4) 0.036(4) -0.022(3) 0.001(3) -0.011(3) C1 0.049(6) 0.048(5) 0.088(8) -0.003(5) -0.030(5) -0.024(4) C2 0.045(5) 0.061(6) 0.079(8) -0.039(6) 0.000(5) -0.020(4) C3 0.044(6) 0.071(7) 0.081(8) -0.013(6) -0.025(5) -0.011(5) C4 0.059(6) 0.054(6) 0.057(6) -0.010(5) -0.015(5) -0.005(5) C5 0.051(5) 0.032(4) 0.050(5) -0.013(4) -0.015(4) -0.006(4) C6 0.057(6) 0.038(5) 0.056(6) 0.002(4) -0.012(4) -0.016(4) C7 0.054(5) 0.051(5) 0.035(5) 0.000(4) -0.013(4) -0.012(4) C8 0.046(5) 0.050(5) 0.037(5) -0.010(4) -0.015(4) -0.009(4) C9 0.076(7) 0.081(7) 0.053(7) -0.031(6) -0.014(5) -0.018(6) O111 0.111(7) 0.069(6) 0.125(8) -0.036(5) -0.047(6) -0.025(5) O222 0.080(6) 0.073(5) 0.083(7) -0.001(5) -0.012(5) -0.031(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.899(6) . ? Cu1 O1 1.910(6) 2_655 ? Cu1 O2 1.943(6) . ? Cu1 N1 1.982(6) . ? Cu1 Cu1 2.998(2) 2_655 ? O1 C7 1.412(9) . ? O1 Cu1 1.910(6) 2_655 ? O2 C8 1.301(10) . ? O3 C8 1.286(11) . ? N1 C1 1.340(11) . ? N1 C5 1.364(11) . ? C1 C2 1.393(12) . ? C1 H1 0.9500 . ? C2 C3 1.356(15) . ? C2 H2 0.9500 . ? C3 C4 1.388(14) . ? C3 H3 0.9500 . ? C4 C5 1.391(12) . ? C4 H4 0.9500 . ? C5 C6 1.491(12) . ? C6 C7 1.510(13) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.430(13) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? O111 H111 0.70(14) . ? O111 H222 0.94(15) . ? O222 H333 1.05(13) . ? O222 H444 0.70(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 76.2(3) . 2_655 ? O1 Cu1 O2 170.7(2) . . ? O1 Cu1 O2 95.8(2) 2_655 . ? O1 Cu1 N1 94.3(3) . . ? O1 Cu1 N1 163.3(3) 2_655 . ? O2 Cu1 N1 94.6(3) . . ? O1 Cu1 Cu1 38.23(17) . 2_655 ? O1 Cu1 Cu1 37.97(18) 2_655 2_655 ? O2 Cu1 Cu1 133.57(18) . 2_655 ? N1 Cu1 Cu1 131.1(2) . 2_655 ? C7 O1 Cu1 125.6(6) . . ? C7 O1 Cu1 130.6(6) . 2_655 ? Cu1 O1 Cu1 103.8(3) . 2_655 ? C8 O2 Cu1 107.5(5) . . ? C1 N1 C5 118.2(7) . . ? C1 N1 Cu1 118.7(6) . . ? C5 N1 Cu1 122.3(6) . . ? N1 C1 C2 124.3(9) . . ? N1 C1 H1 117.8 . . ? C2 C1 H1 117.8 . . ? C3 C2 C1 116.8(9) . . ? C3 C2 H2 121.6 . . ? C1 C2 H2 121.6 . . ? C2 C3 C4 120.8(9) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C5 119.6(9) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 120.1(8) . . ? N1 C5 C6 118.1(7) . . ? C4 C5 C6 121.7(8) . . ? C5 C6 C7 112.6(7) . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? O1 C7 C6 111.8(8) . . ? O1 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? O1 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? O3 C8 O2 116.3(8) . . ? O3 C8 C9 124.1(9) . . ? O2 C8 C9 119.4(8) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? H111 O111 H222 140(10) . . ? H333 O222 H444 103(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 O1 C7 177.8(8) 2_655 . . . ? O2 Cu1 O1 C7 -151.7(14) . . . . ? N1 Cu1 O1 C7 11.7(7) . . . . ? Cu1 Cu1 O1 C7 177.8(8) 2_655 . . . ? O1 Cu1 O1 Cu1 0.0 2_655 . . 2_655 ? O2 Cu1 O1 Cu1 30.5(17) . . . 2_655 ? N1 Cu1 O1 Cu1 -166.2(3) . . . 2_655 ? O1 Cu1 O2 C8 63.8(17) . . . . ? O1 Cu1 O2 C8 93.5(5) 2_655 . . . ? N1 Cu1 O2 C8 -99.5(5) . . . . ? Cu1 Cu1 O2 C8 89.5(5) 2_655 . . . ? O1 Cu1 N1 C1 148.4(7) . . . . ? O1 Cu1 N1 C1 94.2(11) 2_655 . . . ? O2 Cu1 N1 C1 -34.3(7) . . . . ? Cu1 Cu1 N1 C1 137.1(6) 2_655 . . . ? O1 Cu1 N1 C5 -21.8(6) . . . . ? O1 Cu1 N1 C5 -76.0(11) 2_655 . . . ? O2 Cu1 N1 C5 155.5(6) . . . . ? Cu1 Cu1 N1 C5 -33.2(7) 2_655 . . . ? C5 N1 C1 C2 -1.4(14) . . . . ? Cu1 N1 C1 C2 -172.0(7) . . . . ? N1 C1 C2 C3 4.1(15) . . . . ? C1 C2 C3 C4 -2.3(15) . . . . ? C2 C3 C4 C5 -1.8(16) . . . . ? C1 N1 C5 C4 -3.0(12) . . . . ? Cu1 N1 C5 C4 167.2(7) . . . . ? C1 N1 C5 C6 -179.5(8) . . . . ? Cu1 N1 C5 C6 -9.2(10) . . . . ? C3 C4 C5 N1 4.6(14) . . . . ? C3 C4 C5 C6 -179.1(10) . . . . ? N1 C5 C6 C7 58.4(11) . . . . ? C4 C5 C6 C7 -118.0(9) . . . . ? Cu1 O1 C7 C6 27.4(10) . . . . ? Cu1 O1 C7 C6 -155.4(6) 2_655 . . . ? C5 C6 C7 O1 -67.1(10) . . . . ? Cu1 O2 C8 O3 -4.3(9) . . . . ? Cu1 O2 C8 C9 179.8(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2 O3 0.95 2.48 3.387(12) 159.6 1_455 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.897 _refine_diff_density_min -0.987 _refine_diff_density_rms 0.158 #===END data_2c _database_code_depnum_ccdc_archive 'CCDC 747412' #TrackingRef 'ALL-REVISEDR3.cif'.2H2O #TrackingRef 'ALL-REVISEDR3.cif'REGENERATED _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H28 Cu2 N2 O8' _chemical_formula_weight 539.51 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8434(14) _cell_length_b 10.2268(16) _cell_length_c 15.6268(12) _cell_angle_alpha 70.921(10) _cell_angle_beta 76.83(3) _cell_angle_gamma 77.201(14) _cell_volume 1138.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2751 _cell_measurement_theta_min 2.9873 _cell_measurement_theta_max 32.4142 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 1.914 _exptl_absorpt_correction_T_min 0.6673 _exptl_absorpt_correction_T_max 0.7623 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9885 _diffrn_reflns_av_R_equivalents 0.0726 _diffrn_reflns_av_sigmaI/netI 0.0827 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3989 _reflns_number_gt 2788 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0956P)^2^+0.2492P] 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 3989 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1028 _refine_ls_R_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.1773 _refine_ls_wR_factor_gt 0.1613 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.23619(9) 0.59785(8) 0.27454(5) 0.0220(3) Uani 1 1 d . . . Cu2 Cu 0.58465(10) 0.42759(8) 0.21585(5) 0.0225(3) Uani 1 1 d . . . O1 O 0.3643(5) 0.4108(5) 0.2999(3) 0.0243(10) Uani 1 1 d . . . O2 O 0.1424(6) 0.7980(5) 0.2359(3) 0.0288(11) Uani 1 1 d . . . O3 O 0.3136(6) 0.7909(6) 0.3311(4) 0.0398(13) Uani 1 1 d . . . O4 O 0.4543(6) 0.6125(5) 0.1881(3) 0.0273(11) Uani 1 1 d . . . O5 O 0.6784(6) 0.2270(5) 0.2444(3) 0.0276(11) Uani 1 1 d . . . O6 O 0.5773(7) 0.2728(5) 0.1161(3) 0.0398(13) Uani 1 1 d . . . N1 N 0.0112(7) 0.5397(6) 0.3497(4) 0.0237(13) Uani 1 1 d . . . N2 N 0.8157(7) 0.4874(6) 0.1488(4) 0.0261(13) Uani 1 1 d . . . C1 C -0.1425(9) 0.6177(8) 0.3237(5) 0.0274(16) Uani 1 1 d . . . H1 H -0.1379 0.7075 0.2802 0.033 Uiso 1 1 calc R . . C2 C -0.3031(9) 0.5741(8) 0.3568(5) 0.0309(17) Uani 1 1 d . . . H2 H -0.4077 0.6318 0.3368 0.037 Uiso 1 1 calc R . . C3 C -0.3099(9) 0.4431(9) 0.4206(5) 0.0364(19) Uani 1 1 d . . . H3 H -0.4195 0.4089 0.4441 0.044 Uiso 1 1 calc R . . C4 C -0.1575(9) 0.3640(8) 0.4491(5) 0.0322(17) Uani 1 1 d . . . H4 H -0.1606 0.2739 0.4924 0.039 Uiso 1 1 calc R . . C5 C 0.0030(9) 0.4155(8) 0.4147(5) 0.0274(16) Uani 1 1 d . . . C6 C 0.1730(8) 0.3303(8) 0.4446(5) 0.0297(16) Uani 1 1 d . . . H6A H 0.1462 0.2437 0.4936 0.036 Uiso 1 1 calc R . . H6B H 0.2264 0.3846 0.4707 0.036 Uiso 1 1 calc R . . C7 C 0.3064(9) 0.2906(7) 0.3662(5) 0.0284(16) Uani 1 1 d . . . H7A H 0.4096 0.2255 0.3907 0.034 Uiso 1 1 calc R . . H7B H 0.2511 0.2417 0.3370 0.034 Uiso 1 1 calc R . . C8 C 0.2132(9) 0.8579(7) 0.2745(5) 0.0295(16) Uani 1 1 d . . . C9 C 0.1736(11) 1.0191(9) 0.2461(8) 0.065(3) Uani 1 1 d . . . H9A H 0.2539 1.0547 0.2698 0.098 Uiso 1 1 calc R . . H9B H 0.0506 1.0496 0.2717 0.098 Uiso 1 1 calc R . . H9C H 0.1911 1.0556 0.1790 0.098 Uiso 1 1 calc R . . C10 C 0.9653(8) 0.4091(8) 0.1780(4) 0.0251(16) Uani 1 1 d . . . H10 H 0.9569 0.3245 0.2265 0.030 Uiso 1 1 calc R . . C11 C 1.1295(9) 0.4471(9) 0.1403(5) 0.037(2) Uani 1 1 d . . . H11 H 1.2331 0.3890 0.1614 0.044 Uiso 1 1 calc R . . C12 C 1.1410(10) 0.5731(9) 0.0704(5) 0.0363(19) Uani 1 1 d . . . H12 H 1.2523 0.6034 0.0435 0.044 Uiso 1 1 calc R . . C13 C 0.9872(9) 0.6523(9) 0.0414(5) 0.0348(18) Uani 1 1 d . . . H13 H 0.9931 0.7379 -0.0065 0.042 Uiso 1 1 calc R . . C14 C 0.8270(9) 0.6106(8) 0.0797(4) 0.0265(16) Uani 1 1 d . . . C15 C 0.6581(9) 0.6949(8) 0.0480(4) 0.0319(17) Uani 1 1 d . . . H15A H 0.6088 0.6407 0.0199 0.038 Uiso 1 1 calc R . . H15B H 0.6853 0.7823 0.0000 0.038 Uiso 1 1 calc R . . C16 C 0.5183(10) 0.7325(7) 0.1254(5) 0.0332(17) Uani 1 1 d . . . H16A H 0.5706 0.7780 0.1581 0.040 Uiso 1 1 calc R . . H16B H 0.4185 0.8001 0.0992 0.040 Uiso 1 1 calc R . . C17 C 0.6508(8) 0.1890(8) 0.1788(5) 0.0277(16) Uani 1 1 d . . . C18 C 0.7085(11) 0.0352(8) 0.1852(6) 0.0413(19) Uani 1 1 d . . . H18A H 0.8073 -0.0035 0.2206 0.050 Uiso 1 1 calc R . . H18B H 0.6085 -0.0162 0.2185 0.050 Uiso 1 1 calc R . . C19 C 0.7674(19) 0.0136(13) 0.0915(9) 0.108(5) Uani 1 1 d . . . H19A H 0.6728 0.0579 0.0548 0.162 Uiso 1 1 calc R . . H19B H 0.7936 -0.0870 0.0978 0.162 Uiso 1 1 calc R . . H19C H 0.8743 0.0559 0.0610 0.162 Uiso 1 1 calc R . . O111 O 0.7366(7) 0.0204(6) 0.4108(4) 0.0437(14) Uani 1 1 d . . . O222 O 0.4649(8) 0.8693(6) 0.4469(4) 0.0500(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0184(4) 0.0276(5) 0.0215(5) -0.0109(4) -0.0018(3) -0.0027(4) Cu2 0.0182(4) 0.0297(5) 0.0201(5) -0.0105(4) -0.0003(3) -0.0032(4) O1 0.021(2) 0.028(3) 0.021(2) -0.008(2) 0.0040(19) -0.004(2) O2 0.027(2) 0.028(3) 0.038(3) -0.017(2) -0.008(2) -0.005(2) O3 0.033(3) 0.053(4) 0.044(3) -0.030(3) -0.011(3) 0.002(3) O4 0.026(2) 0.028(3) 0.026(3) -0.012(2) 0.007(2) -0.006(2) O5 0.023(2) 0.037(3) 0.020(2) -0.011(2) 0.0029(19) -0.002(2) O6 0.049(3) 0.042(3) 0.034(3) -0.012(2) -0.018(3) -0.005(3) N1 0.025(3) 0.032(3) 0.022(3) -0.018(3) -0.003(2) -0.004(3) N2 0.024(3) 0.038(4) 0.017(3) -0.013(3) 0.001(2) -0.005(3) C1 0.027(4) 0.035(4) 0.028(4) -0.019(3) -0.009(3) -0.003(3) C2 0.022(4) 0.044(5) 0.034(4) -0.023(4) -0.003(3) -0.003(3) C3 0.019(4) 0.063(6) 0.038(4) -0.033(4) 0.004(3) -0.010(4) C4 0.029(4) 0.041(4) 0.026(4) -0.012(3) 0.005(3) -0.010(3) C5 0.026(4) 0.039(4) 0.022(4) -0.019(3) 0.000(3) -0.005(3) C6 0.026(4) 0.034(4) 0.025(4) -0.007(3) -0.001(3) -0.002(3) C7 0.027(4) 0.033(4) 0.024(4) -0.011(3) 0.001(3) -0.004(3) C8 0.020(3) 0.029(4) 0.043(4) -0.022(3) 0.003(3) -0.001(3) C9 0.041(5) 0.043(5) 0.132(10) -0.050(6) -0.023(6) -0.001(4) C10 0.015(3) 0.047(4) 0.015(3) -0.013(3) -0.001(3) -0.004(3) C11 0.018(3) 0.077(6) 0.025(4) -0.029(4) -0.001(3) -0.006(4) C12 0.030(4) 0.060(5) 0.030(4) -0.026(4) 0.007(3) -0.024(4) C13 0.034(4) 0.049(5) 0.027(4) -0.019(4) 0.007(3) -0.017(4) C14 0.027(4) 0.038(4) 0.017(3) -0.017(3) 0.006(3) -0.007(3) C15 0.033(4) 0.040(4) 0.017(4) -0.003(3) 0.002(3) -0.008(3) C16 0.038(4) 0.026(4) 0.028(4) -0.004(3) 0.006(3) -0.006(3) C17 0.017(3) 0.037(4) 0.028(4) -0.013(3) 0.003(3) -0.004(3) C18 0.042(5) 0.038(5) 0.047(5) -0.024(4) -0.005(4) -0.001(4) C19 0.145(12) 0.071(8) 0.103(10) -0.033(7) 0.033(9) -0.053(8) O111 0.042(3) 0.050(4) 0.038(3) -0.004(3) -0.013(3) -0.013(3) O222 0.064(4) 0.062(4) 0.036(3) -0.017(3) -0.014(3) -0.025(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.913(4) . ? Cu1 O4 1.924(4) . ? Cu1 O2 1.955(5) . ? Cu1 N1 1.977(5) . ? Cu1 Cu2 3.0226(12) . ? Cu2 O4 1.902(5) . ? Cu2 O1 1.921(4) . ? Cu2 O5 1.957(5) . ? Cu2 N2 1.991(6) . ? O1 C7 1.411(8) . ? O2 C8 1.261(8) . ? O3 C8 1.248(8) . ? O4 C16 1.408(8) . ? O5 C17 1.284(8) . ? O6 C17 1.231(8) . ? N1 C5 1.347(9) . ? N1 C1 1.356(8) . ? N2 C10 1.348(8) . ? N2 C14 1.370(9) . ? C1 C2 1.362(9) . ? C1 H1 0.9500 . ? C2 C3 1.387(11) . ? C2 H2 0.9500 . ? C3 C4 1.364(10) . ? C3 H3 0.9500 . ? C4 C5 1.397(9) . ? C4 H4 0.9500 . ? C5 C6 1.502(9) . ? C6 C7 1.521(9) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.539(10) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.372(9) . ? C10 H10 0.9500 . ? C11 C12 1.396(11) . ? C11 H11 0.9500 . ? C12 C13 1.376(10) . ? C12 H12 0.9500 . ? C13 C14 1.359(9) . ? C13 H13 0.9500 . ? C14 C15 1.503(9) . ? C15 C16 1.526(9) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.514(10) . ? C18 C19 1.503(14) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O4 75.61(18) . . ? O1 Cu1 O2 170.44(18) . . ? O4 Cu1 O2 95.0(2) . . ? O1 Cu1 N1 93.9(2) . . ? O4 Cu1 N1 164.0(2) . . ? O2 Cu1 N1 95.7(2) . . ? O1 Cu1 Cu2 38.08(13) . . ? O4 Cu1 Cu2 37.56(14) . . ? O2 Cu1 Cu2 132.47(14) . . ? N1 Cu1 Cu2 131.17(16) . . ? O4 Cu2 O1 75.94(18) . . ? O4 Cu2 O5 169.56(19) . . ? O1 Cu2 O5 96.65(19) . . ? O4 Cu2 N2 94.4(2) . . ? O1 Cu2 N2 162.1(2) . . ? O5 Cu2 N2 94.6(2) . . ? O4 Cu2 Cu1 38.07(13) . . ? O1 Cu2 Cu1 37.89(13) . . ? O5 Cu2 Cu1 134.30(13) . . ? N2 Cu2 Cu1 130.44(17) . . ? C7 O1 Cu1 126.7(4) . . ? C7 O1 Cu2 129.2(4) . . ? Cu1 O1 Cu2 104.0(2) . . ? C8 O2 Cu1 107.4(4) . . ? C16 O4 Cu2 125.7(4) . . ? C16 O4 Cu1 129.5(4) . . ? Cu2 O4 Cu1 104.4(2) . . ? C17 O5 Cu2 105.0(4) . . ? C5 N1 C1 118.1(6) . . ? C5 N1 Cu1 123.2(5) . . ? C1 N1 Cu1 117.7(5) . . ? C10 N2 C14 119.0(6) . . ? C10 N2 Cu2 118.3(4) . . ? C14 N2 Cu2 122.5(5) . . ? N1 C1 C2 123.4(7) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C1 C2 C3 118.3(7) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 119.3(7) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 120.0(7) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? N1 C5 C4 120.7(6) . . ? N1 C5 C6 118.1(6) . . ? C4 C5 C6 121.1(6) . . ? C5 C6 C7 112.7(6) . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? O1 C7 C6 110.8(6) . . ? O1 C7 H7A 109.5 . . ? C6 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? O3 C8 O2 122.2(7) . . ? O3 C8 C9 121.2(7) . . ? O2 C8 C9 116.6(6) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C11 122.5(7) . . ? N2 C10 H10 118.8 . . ? C11 C10 H10 118.8 . . ? C10 C11 C12 118.6(7) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C13 C12 C11 118.4(7) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C14 C13 C12 121.4(7) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 N2 120.2(7) . . ? C13 C14 C15 122.0(7) . . ? N2 C14 C15 117.7(6) . . ? C14 C15 C16 113.1(6) . . ? C14 C15 H15A 109.0 . . ? C16 C15 H15A 109.0 . . ? C14 C15 H15B 109.0 . . ? C16 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? O4 C16 C15 111.1(6) . . ? O4 C16 H16A 109.4 . . ? C15 C16 H16A 109.4 . . ? O4 C16 H16B 109.4 . . ? C15 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? O6 C17 O5 121.5(7) . . ? O6 C17 C18 122.5(7) . . ? O5 C17 C18 116.0(6) . . ? C19 C18 C17 111.4(8) . . ? C19 C18 H18A 109.3 . . ? C17 C18 H18A 109.3 . . ? C19 C18 H18B 109.3 . . ? C17 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 Cu2 O4 177.3(3) . . . . ? O2 Cu1 Cu2 O4 -4.8(3) . . . . ? N1 Cu1 Cu2 O4 163.2(3) . . . . ? O4 Cu1 Cu2 O1 -177.3(3) . . . . ? O2 Cu1 Cu2 O1 177.9(3) . . . . ? N1 Cu1 Cu2 O1 -14.1(3) . . . . ? O1 Cu1 Cu2 O5 8.0(3) . . . . ? O4 Cu1 Cu2 O5 -169.3(3) . . . . ? O2 Cu1 Cu2 O5 -174.1(3) . . . . ? N1 Cu1 Cu2 O5 -6.1(3) . . . . ? O1 Cu1 Cu2 N2 -160.3(3) . . . . ? O4 Cu1 Cu2 N2 22.5(3) . . . . ? O2 Cu1 Cu2 N2 17.7(3) . . . . ? N1 Cu1 Cu2 N2 -174.3(3) . . . . ? O4 Cu1 O1 C7 -178.6(5) . . . . ? O2 Cu1 O1 C7 170.4(10) . . . . ? N1 Cu1 O1 C7 -10.9(5) . . . . ? Cu2 Cu1 O1 C7 179.6(6) . . . . ? O4 Cu1 O1 Cu2 1.7(2) . . . . ? O2 Cu1 O1 Cu2 -9.2(13) . . . . ? N1 Cu1 O1 Cu2 169.4(2) . . . . ? O4 Cu2 O1 C7 178.6(5) . . . . ? O5 Cu2 O1 C7 6.1(5) . . . . ? N2 Cu2 O1 C7 -122.6(7) . . . . ? Cu1 Cu2 O1 C7 -179.6(6) . . . . ? O4 Cu2 O1 Cu1 -1.7(2) . . . . ? O5 Cu2 O1 Cu1 -174.3(2) . . . . ? N2 Cu2 O1 Cu1 57.0(7) . . . . ? O1 Cu1 O2 C8 -70.3(13) . . . . ? O4 Cu1 O2 C8 -81.0(4) . . . . ? N1 Cu1 O2 C8 111.0(4) . . . . ? Cu2 Cu1 O2 C8 -78.0(5) . . . . ? O1 Cu2 O4 C16 174.7(6) . . . . ? O5 Cu2 O4 C16 -139.7(10) . . . . ? N2 Cu2 O4 C16 10.0(5) . . . . ? Cu1 Cu2 O4 C16 173.0(6) . . . . ? O1 Cu2 O4 Cu1 1.7(2) . . . . ? O5 Cu2 O4 Cu1 47.3(11) . . . . ? N2 Cu2 O4 Cu1 -163.0(2) . . . . ? O1 Cu1 O4 C16 -174.4(6) . . . . ? O2 Cu1 O4 C16 3.8(6) . . . . ? N1 Cu1 O4 C16 135.4(8) . . . . ? Cu2 Cu1 O4 C16 -172.6(7) . . . . ? O1 Cu1 O4 Cu2 -1.7(2) . . . . ? O2 Cu1 O4 Cu2 176.4(2) . . . . ? N1 Cu1 O4 Cu2 -52.0(8) . . . . ? O4 Cu2 O5 C17 56.6(11) . . . . ? O1 Cu2 O5 C17 100.8(4) . . . . ? N2 Cu2 O5 C17 -93.0(4) . . . . ? Cu1 Cu2 O5 C17 95.9(4) . . . . ? O1 Cu1 N1 C5 18.9(5) . . . . ? O4 Cu1 N1 C5 67.2(9) . . . . ? O2 Cu1 N1 C5 -161.3(5) . . . . ? Cu2 Cu1 N1 C5 27.6(6) . . . . ? O1 Cu1 N1 C1 -149.4(5) . . . . ? O4 Cu1 N1 C1 -101.1(8) . . . . ? O2 Cu1 N1 C1 30.3(5) . . . . ? Cu2 Cu1 N1 C1 -140.8(4) . . . . ? O4 Cu2 N2 C10 151.2(5) . . . . ? O1 Cu2 N2 C10 94.9(8) . . . . ? O5 Cu2 N2 C10 -34.1(5) . . . . ? Cu1 Cu2 N2 C10 137.5(4) . . . . ? O4 Cu2 N2 C14 -23.0(5) . . . . ? O1 Cu2 N2 C14 -79.3(8) . . . . ? O5 Cu2 N2 C14 151.7(5) . . . . ? Cu1 Cu2 N2 C14 -36.7(6) . . . . ? C5 N1 C1 C2 -3.1(9) . . . . ? Cu1 N1 C1 C2 165.8(5) . . . . ? N1 C1 C2 C3 0.1(10) . . . . ? C1 C2 C3 C4 1.2(11) . . . . ? C2 C3 C4 C5 0.4(11) . . . . ? C1 N1 C5 C4 4.8(9) . . . . ? Cu1 N1 C5 C4 -163.5(5) . . . . ? C1 N1 C5 C6 -179.0(6) . . . . ? Cu1 N1 C5 C6 12.7(8) . . . . ? C3 C4 C5 N1 -3.6(11) . . . . ? C3 C4 C5 C6 -179.6(7) . . . . ? N1 C5 C6 C7 -60.4(9) . . . . ? C4 C5 C6 C7 115.7(7) . . . . ? Cu1 O1 C7 C6 -26.4(7) . . . . ? Cu2 O1 C7 C6 153.1(4) . . . . ? C5 C6 C7 O1 65.9(8) . . . . ? Cu1 O2 C8 O3 -4.5(8) . . . . ? Cu1 O2 C8 C9 173.8(6) . . . . ? C14 N2 C10 C11 -1.0(10) . . . . ? Cu2 N2 C10 C11 -175.3(5) . . . . ? N2 C10 C11 C12 1.4(10) . . . . ? C10 C11 C12 C13 -1.1(11) . . . . ? C11 C12 C13 C14 0.5(11) . . . . ? C12 C13 C14 N2 -0.1(10) . . . . ? C12 C13 C14 C15 -179.1(7) . . . . ? C10 N2 C14 C13 0.3(10) . . . . ? Cu2 N2 C14 C13 174.4(5) . . . . ? C10 N2 C14 C15 179.4(6) . . . . ? Cu2 N2 C14 C15 -6.5(8) . . . . ? C13 C14 C15 C16 -124.5(7) . . . . ? N2 C14 C15 C16 56.5(9) . . . . ? Cu2 O4 C16 C15 29.8(8) . . . . ? Cu1 O4 C16 C15 -159.0(4) . . . . ? C14 C15 C16 O4 -68.1(8) . . . . ? Cu2 O5 C17 O6 -0.7(7) . . . . ? Cu2 O5 C17 C18 -178.8(5) . . . . ? O6 C17 C18 C19 33.8(11) . . . . ? O5 C17 C18 C19 -148.1(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2 O3 0.95 2.42 3.336(9) 162.4 1_455 C4 H4 O3 0.95 2.67 3.345(9) 128.4 2_566 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.212 _refine_diff_density_min -0.866 _refine_diff_density_rms 0.132