# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. #============================================================================== # PROCESSING SUMMARY _journal_coden_Cambridge 0182 #TrackingRef '- CC-COM-10-2010-004689-rev.cif' _audit_creation_date 2010-12-02 _audit_creation_method 'by CrystalStructure 4.0' _audit_update_record ? _publ_contact_author_name 'Wei-Yin Sun' _publ_contact_author_address ; ; _publ_contact_author_email sunwy@nju.edu.cn #============================================================================== # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Rigaku (2010). CrystalStructure. Version 4.0. Rigaku Corporation, Tokyo, Japan. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M., Polidori, G., and Camalli, M. (1994) J. Appl. Cryst., 27, 435. SIR92 Sheldrick, G.M. (2008), Acta Cryst. A64, 112-122. Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; loop_ _publ_author_name M.-S.Chen M.Chen S.Takamizawa T.-a.Okamura J.Fan 'Wei-Yin Su.' data_1 _database_code_depnum_ccdc_archive 'CCDC 787827' #TrackingRef '- CC-COM-10-2010-004689-rev.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C14 H12 Cu N2 O7' _chemical_formula_moiety 'C14 H12 Cu N2 O7' _chemical_formula_weight 383.80 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 8.405(5) _cell_length_b 10.293(4) _cell_length_c 17.812(8) _cell_angle_alpha 90.0000 _cell_angle_beta 104.582(19) _cell_angle_gamma 90.0000 _cell_volume 1491.2(12) _cell_formula_units_Z 4 _cell_measurement_reflns_used 11480 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 27.48 _cell_measurement_temperature 293(1) #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.150 _exptl_crystal_density_diffrn 1.709 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780.00 _exptl_absorpt_coefficient_mu 1.506 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.539 _exptl_absorpt_correction_T_max 0.798 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 293(1) _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_source ; MicroMax-007HF microfocus rotating anode X-ray generator ; _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 13613 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). The summation of the occupancies for O3, O3B, and O3C were restrained using SUMP command. ; _reflns_number_total 3410 _reflns_number_gt 3008 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1381 _refine_ls_number_restraints 4 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3410 _refine_ls_number_parameters 222 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0814P)^2^+1.8234P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.900 _refine_diff_density_min -0.480 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; Cu Cu 0.320 1.265 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu(1) Cu 0.60564(4) 0.55755(3) 0.931976(19) 0.02394(15) Uani 1.0 4 d . . . O(1) O 0.1244(4) 0.4591(3) 0.43674(13) 0.0411(7) Uani 1.0 4 d . . . O(2) O 0.1037(19) 0.9075(14) 0.7897(8) 0.116(5) Uiso 0.467(13) 4 d . . . O(2B) O -0.003(3) 0.9470(14) 0.7854(9) 0.151(6) Uiso 0.533(13) 4 d . . . O(3) O 0.1568(13) 0.6501(14) 0.7940(6) 0.091(4) Uiso 0.467(13) 4 d . . . O(3B) O 0.228(3) 0.7824(19) 0.7932(11) 0.089(6) Uiso 0.244(10) 4 d . . . O(3C) O 0.153(3) 0.5646(19) 0.7937(10) 0.087(6) Uiso 0.289(15) 4 d . . . O(31) O 0.5309(3) 0.5375(2) 0.82375(12) 0.0289(5) Uani 1.0 4 d . . . O(32) O 0.6936(3) 0.7026(3) 0.81292(13) 0.0350(6) Uani 1.0 4 d . . . O(51) O 0.6220(3) 0.8908(3) 0.54178(12) 0.0326(5) Uani 1.0 4 d . . . O(52) O 0.4729(3) 0.7847(2) 0.44385(12) 0.0290(5) Uani 1.0 4 d . . . N(1) N 0.2349(3) 0.3984(3) 0.56182(14) 0.0244(5) Uani 1.0 4 d . . . N(11) N -0.2157(3) 0.0722(3) 0.45068(15) 0.0240(5) Uani 1.0 4 d . . . C(1) C 0.3437(4) 0.5029(3) 0.58786(16) 0.0221(6) Uani 1.0 4 d . . . C(2) C 0.4129(4) 0.5119(3) 0.66700(16) 0.0239(6) Uani 1.0 4 d . . . C(3) C 0.5208(4) 0.6120(3) 0.69788(16) 0.0223(6) Uani 1.0 4 d . . . C(4) C 0.5612(4) 0.7048(3) 0.64908(16) 0.0228(6) Uani 1.0 4 d . . . C(5) C 0.4923(4) 0.6949(3) 0.56946(16) 0.0219(6) Uani 1.0 4 d . . . C(6) C 0.3846(4) 0.5950(3) 0.53778(16) 0.0220(6) Uani 1.0 4 d . . . C(11) C 0.1315(4) 0.3848(3) 0.49097(17) 0.0250(6) Uani 1.0 4 d . . . C(12) C -0.1424(4) 0.1073(3) 0.52380(17) 0.0262(6) Uani 1.0 4 d . . . C(13) C -0.0258(4) 0.2051(3) 0.54055(17) 0.0265(6) Uani 1.0 4 d . . . C(14) C 0.0171(4) 0.2690(3) 0.48026(17) 0.0243(6) Uani 1.0 4 d . . . C(15) C -0.0571(4) 0.2313(4) 0.40468(18) 0.0318(7) Uani 1.0 4 d . . . C(16) C -0.1727(4) 0.1334(4) 0.39206(18) 0.0312(7) Uani 1.0 4 d . . . C(31) C 0.5896(4) 0.6208(3) 0.78422(16) 0.0230(6) Uani 1.0 4 d . . . C(51) C 0.5310(4) 0.7931(3) 0.51648(16) 0.0219(6) Uani 1.0 4 d . . . H(1) H 0.2346 0.3371 0.5946 0.0293 Uiso 1.0 4 calc R . . H(2) H 0.3867 0.4500 0.7000 0.0287 Uiso 1.0 4 calc R . . H(3) H 0.6329 0.7723 0.6692 0.0273 Uiso 1.0 4 calc R . . H(4) H 0.3407 0.5895 0.4845 0.0264 Uiso 1.0 4 calc R . . H(5) H -0.1708 0.0645 0.5645 0.0314 Uiso 1.0 4 calc R . . H(6) H 0.0230 0.2276 0.5917 0.0319 Uiso 1.0 4 calc R . . H(7) H -0.0292 0.2716 0.3631 0.0382 Uiso 1.0 4 calc R . . H(8) H -0.2226 0.1089 0.3413 0.0375 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu(1) 0.0295(3) 0.0245(3) 0.0176(2) 0.00747(13) 0.00544(15) 0.00034(13) O(1) 0.0483(15) 0.0419(14) 0.0249(12) -0.0219(11) -0.0060(11) 0.0096(10) O(31) 0.0360(12) 0.0327(11) 0.0159(10) -0.0007(9) 0.0028(9) 0.0025(9) O(32) 0.0403(13) 0.0376(13) 0.0235(11) -0.0080(10) 0.0010(10) -0.0056(10) O(51) 0.0426(13) 0.0315(12) 0.0214(10) -0.0180(10) 0.0039(9) 0.0016(9) O(52) 0.0365(12) 0.0286(11) 0.0213(10) -0.0099(9) 0.0059(9) 0.0017(9) N(1) 0.0273(13) 0.0222(12) 0.0213(12) -0.0080(10) 0.0014(10) 0.0038(10) N(11) 0.0240(12) 0.0242(12) 0.0236(12) -0.0055(9) 0.0058(10) -0.0003(10) C(1) 0.0214(13) 0.0207(13) 0.0238(13) -0.0034(10) 0.0050(11) -0.0000(11) C(2) 0.0278(15) 0.0214(13) 0.0220(13) -0.0024(11) 0.0055(11) 0.0042(11) C(3) 0.0261(14) 0.0207(13) 0.0192(13) 0.0003(11) 0.0043(11) -0.0001(11) C(4) 0.0259(14) 0.0206(13) 0.0211(13) -0.0037(11) 0.0046(11) -0.0015(11) C(5) 0.0234(13) 0.0217(13) 0.0209(13) -0.0026(11) 0.0061(11) -0.0002(11) C(6) 0.0236(14) 0.0239(13) 0.0173(13) -0.0029(11) 0.0029(10) 0.0013(11) C(11) 0.0247(14) 0.0246(14) 0.0251(14) -0.0041(11) 0.0050(11) -0.0000(12) C(12) 0.0268(15) 0.0273(14) 0.0234(14) -0.0036(12) 0.0045(11) 0.0034(12) C(13) 0.0268(15) 0.0288(15) 0.0219(13) -0.0055(12) 0.0023(11) -0.0003(12) C(14) 0.0216(14) 0.0235(14) 0.0266(14) -0.0036(11) 0.0040(11) -0.0006(11) C(15) 0.0376(17) 0.0340(16) 0.0244(15) -0.0130(13) 0.0088(13) 0.0006(13) C(16) 0.0353(17) 0.0375(17) 0.0210(14) -0.0134(14) 0.0072(12) -0.0059(13) C(31) 0.0269(14) 0.0220(13) 0.0190(13) 0.0058(11) 0.0038(11) -0.0013(11) C(51) 0.0234(14) 0.0227(13) 0.0202(13) -0.0022(11) 0.0066(11) 0.0018(11) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, 1998)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SIR92 (Altomare, et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Cu(1) O(31) 1.882(3) yes . . Cu(1) O(51) 1.998(3) yes . 4_565 Cu(1) O(52) 2.011(3) yes . 4_565 Cu(1) N(11) 1.974(3) yes . 4_655 O(1) C(11) 1.222(4) yes . . O(31) C(31) 1.284(4) yes . . O(32) C(31) 1.229(4) yes . . O(51) C(51) 1.276(4) yes . . O(52) C(51) 1.265(4) yes . . N(1) C(1) 1.413(4) yes . . N(1) C(11) 1.347(4) yes . . N(11) C(12) 1.343(4) yes . . N(11) C(16) 1.344(5) yes . . C(1) C(2) 1.386(4) yes . . C(1) C(6) 1.403(5) yes . . C(2) C(3) 1.391(4) yes . . C(3) C(4) 1.391(5) yes . . C(3) C(31) 1.503(4) yes . . C(4) C(5) 1.394(4) yes . . C(5) C(6) 1.392(4) yes . . C(5) C(51) 1.474(5) yes . . C(11) C(14) 1.513(4) yes . . C(12) C(13) 1.384(5) yes . . C(13) C(14) 1.382(5) yes . . C(14) C(15) 1.389(5) yes . . C(15) C(16) 1.378(5) yes . . N(1) H(1) 0.860 no . . C(2) H(2) 0.930 no . . C(4) H(3) 0.930 no . . C(6) H(4) 0.930 no . . C(12) H(5) 0.930 no . . C(13) H(6) 0.930 no . . C(15) H(7) 0.930 no . . C(16) H(8) 0.930 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O(31) Cu(1) O(51) 162.69(10) yes . . 4_565 O(31) Cu(1) O(52) 98.36(9) yes . . 4_565 O(31) Cu(1) N(11) 98.18(11) yes . . 4_655 O(51) Cu(1) O(52) 65.52(9) yes 4_565 . 4_565 O(51) Cu(1) N(11) 98.78(11) yes 4_565 . 4_655 O(52) Cu(1) N(11) 161.24(9) yes 4_565 . 4_655 Cu(1) O(31) C(31) 114.39(18) yes . . . Cu(1) O(51) C(51) 88.66(17) yes 4_564 . . Cu(1) O(52) C(51) 88.38(17) yes 4_564 . . C(1) N(1) C(11) 126.8(3) yes . . . Cu(1) N(11) C(12) 119.3(3) yes 4_454 . . Cu(1) N(11) C(16) 121.8(2) yes 4_454 . . C(12) N(11) C(16) 118.7(3) yes . . . N(1) C(1) C(2) 117.1(3) yes . . . N(1) C(1) C(6) 123.2(3) yes . . . C(2) C(1) C(6) 119.6(3) yes . . . C(1) C(2) C(3) 121.1(3) yes . . . C(2) C(3) C(4) 120.0(3) yes . . . C(2) C(3) C(31) 119.6(3) yes . . . C(4) C(3) C(31) 120.4(3) yes . . . C(3) C(4) C(5) 118.8(3) yes . . . C(4) C(5) C(6) 121.9(3) yes . . . C(4) C(5) C(51) 119.9(3) yes . . . C(6) C(5) C(51) 118.2(3) yes . . . C(1) C(6) C(5) 118.7(3) yes . . . O(1) C(11) N(1) 124.5(3) yes . . . O(1) C(11) C(14) 119.4(3) yes . . . N(1) C(11) C(14) 116.1(3) yes . . . N(11) C(12) C(13) 122.2(3) yes . . . C(12) C(13) C(14) 119.2(3) yes . . . C(11) C(14) C(13) 124.0(3) yes . . . C(11) C(14) C(15) 117.3(3) yes . . . C(13) C(14) C(15) 118.6(3) yes . . . C(14) C(15) C(16) 119.3(3) yes . . . N(11) C(16) C(15) 122.1(3) yes . . . O(31) C(31) O(32) 124.1(3) yes . . . O(31) C(31) C(3) 114.8(3) yes . . . O(32) C(31) C(3) 121.1(3) yes . . . O(51) C(51) O(52) 117.2(3) yes . . . O(51) C(51) C(5) 121.6(3) yes . . . O(52) C(51) C(5) 121.2(3) yes . . . C(1) N(1) H(1) 116.617 no . . . C(11) N(1) H(1) 116.626 no . . . C(1) C(2) H(2) 119.446 no . . . C(3) C(2) H(2) 119.460 no . . . C(3) C(4) H(3) 120.623 no . . . C(5) C(4) H(3) 120.624 no . . . C(1) C(6) H(4) 120.667 no . . . C(5) C(6) H(4) 120.659 no . . . N(11) C(12) H(5) 118.922 no . . . C(13) C(12) H(5) 118.924 no . . . C(12) C(13) H(6) 120.403 no . . . C(14) C(13) H(6) 120.406 no . . . C(14) C(15) H(7) 120.368 no . . . C(16) C(15) H(7) 120.370 no . . . N(11) C(16) H(8) 118.921 no . . . C(15) C(16) H(8) 118.932 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 O(31) Cu(1) O(52) C(51) 176.39(12) no . . 4_565 4_565 O(52) Cu(1) O(31) C(31) 74.44(17) no 4_565 . . . O(31) Cu(1) N(11) C(12) -169.13(17) no . . 4_655 4_655 O(31) Cu(1) N(11) C(16) 6.1(2) no . . 4_655 4_655 N(11) Cu(1) O(31) C(31) -96.67(17) no 4_655 . . . O(51) Cu(1) O(52) C(51) 2.98(11) no 4_565 . 4_565 4_565 O(52) Cu(1) O(51) C(51) -2.96(11) no 4_565 . 4_565 4_565 O(51) Cu(1) N(11) C(12) 7.38(19) no 4_565 . 4_655 4_655 O(51) Cu(1) N(11) C(16) -177.37(18) no 4_565 . 4_655 4_655 N(11) Cu(1) O(51) C(51) 166.28(13) no 4_655 . 4_565 4_565 Cu(1) O(31) C(31) O(32) 4.4(4) no . . . . Cu(1) O(31) C(31) C(3) -175.55(15) no . . . . Cu(1) O(51) C(51) O(52) -4.8(3) no 4_564 . . . Cu(1) O(51) C(51) C(5) 176.2(3) no 4_564 . . . Cu(1) O(52) C(51) O(51) 4.8(3) no 4_564 . . . Cu(1) O(52) C(51) C(5) -176.3(3) no 4_564 . . . C(1) N(1) C(11) O(1) 4.6(5) no . . . . C(1) N(1) C(11) C(14) -174.8(3) no . . . . C(11) N(1) C(1) C(2) 166.5(3) no . . . . C(11) N(1) C(1) C(6) -14.1(5) no . . . . Cu(1) N(11) C(12) C(13) -174.65(18) no 4_454 . . . Cu(1) N(11) C(16) C(15) 174.78(19) no 4_454 . . . C(12) N(11) C(16) C(15) -0.5(5) no . . . . C(16) N(11) C(12) C(13) 0.7(5) no . . . . N(1) C(1) C(2) C(3) -179.7(3) no . . . . N(1) C(1) C(6) C(5) 179.5(3) no . . . . C(2) C(1) C(6) C(5) -1.1(5) no . . . . C(6) C(1) C(2) C(3) 0.9(5) no . . . . C(1) C(2) C(3) C(4) -0.2(5) no . . . . C(1) C(2) C(3) C(31) 178.2(3) no . . . . C(2) C(3) C(4) C(5) -0.3(5) no . . . . C(2) C(3) C(31) O(31) -5.1(4) no . . . . C(2) C(3) C(31) O(32) 175.0(3) no . . . . C(4) C(3) C(31) O(31) 173.3(3) no . . . . C(4) C(3) C(31) O(32) -6.6(5) no . . . . C(31) C(3) C(4) C(5) -178.7(3) no . . . . C(3) C(4) C(5) C(6) 0.0(5) no . . . . C(3) C(4) C(5) C(51) 179.1(3) no . . . . C(4) C(5) C(6) C(1) 0.6(5) no . . . . C(4) C(5) C(51) O(51) -2.7(5) no . . . . C(4) C(5) C(51) O(52) 178.4(3) no . . . . C(6) C(5) C(51) O(51) 176.4(3) no . . . . C(6) C(5) C(51) O(52) -2.5(5) no . . . . C(51) C(5) C(6) C(1) -178.4(3) no . . . . O(1) C(11) C(14) C(13) -157.5(3) no . . . . O(1) C(11) C(14) C(15) 18.0(5) no . . . . N(1) C(11) C(14) C(13) 22.0(5) no . . . . N(1) C(11) C(14) C(15) -162.6(3) no . . . . N(11) C(12) C(13) C(14) -0.1(5) no . . . . C(12) C(13) C(14) C(11) 174.5(3) no . . . . C(12) C(13) C(14) C(15) -0.8(5) no . . . . C(11) C(14) C(15) C(16) -174.6(3) no . . . . C(13) C(14) C(15) C(16) 1.1(5) no . . . . C(14) C(15) C(16) N(11) -0.4(5) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 Cu(1) Cu(1) 3.5490(13) no . 3_667 Cu(1) O(32) 2.840(3) no . . Cu(1) O(51) 2.697(3) no . 2_646 Cu(1) C(51) 3.179(3) no . 2_646 O(1) O(1) 3.540(5) no . 3_566 O(1) N(1) 3.363(4) no . 3_566 O(1) C(1) 2.889(4) no . . O(1) C(6) 2.828(4) no . . O(1) C(11) 3.203(5) no . 3_566 O(1) C(13) 3.600(5) no . 3_566 O(1) C(14) 3.509(5) no . 3_566 O(1) C(15) 2.778(5) no . . O(31) O(51) 3.349(4) no . 2_646 O(31) C(2) 2.730(4) no . . O(31) C(4) 3.570(4) no . 2_646 O(31) C(16) 3.042(4) no . 4_655 O(32) O(52) 3.328(4) no . 4_565 O(32) N(1) 2.954(4) no . 2_656 O(32) C(2) 3.351(4) no . 2_656 O(32) C(4) 2.850(4) no . . O(32) C(13) 3.307(4) no . 2_656 O(51) O(51) 3.152(4) no . 3_676 O(51) O(52) 3.458(4) no . 3_676 O(51) N(11) 3.472(5) no . 3_566 O(51) C(4) 2.841(4) no . . O(51) C(12) 3.051(4) no . 1_665 O(51) C(14) 3.558(5) no . 3_666 O(51) C(51) 3.556(4) no . 3_676 O(52) N(1) 3.117(4) no . 3_666 O(52) N(11) 3.524(4) no . 3_566 O(52) C(1) 3.449(4) no . 3_666 O(52) C(6) 2.791(4) no . . O(52) C(12) 3.177(5) no . 3_566 O(52) C(31) 3.375(4) no . 4_564 N(1) C(13) 2.913(4) no . . N(1) C(51) 3.329(5) no . 3_666 N(11) C(5) 3.296(4) no . 3_566 N(11) C(12) 3.462(5) no . 3_556 N(11) C(13) 3.483(4) no . 3_556 N(11) C(14) 2.773(4) no . . N(11) C(51) 3.173(5) no . 3_566 C(1) C(4) 2.801(4) no . . C(2) C(5) 2.756(5) no . . C(3) C(6) 2.798(4) no . . C(4) C(16) 3.573(5) no . 3_566 C(5) C(16) 3.426(5) no . 3_566 C(6) C(6) 3.274(5) no . 3_666 C(6) C(11) 3.002(4) no . . C(6) C(14) 3.594(5) no . 3_566 C(11) C(11) 3.313(5) no . 3_566 C(11) C(51) 3.407(5) no . 3_666 C(12) C(12) 3.514(5) no . 3_556 C(12) C(15) 2.722(5) no . . C(12) C(51) 3.325(5) no . 3_566 C(13) C(16) 2.724(5) no . . C(16) C(31) 3.549(5) no . 4_454 O(1) O(2) 2.923(14) no . 4_564 O(1) O(2B) 2.809(15) no . 4_564 O(2) O(1) 2.923(14) no . 4_565 O(2) O(3) 3.407(19) no . 2_556 O(2) O(3C) 3.55(3) no . . O(2) O(3C) 2.80(3) no . 2_556 O(2) C(16) 3.456(16) no . 3_566 O(2B) O(1) 2.809(15) no . 4_565 O(2B) O(3) 3.33(2) no . . O(2B) O(3) 2.668(19) no . 2_556 O(2B) O(3B) 2.56(3) no . . O(3) O(2) 3.407(19) no . 2_546 O(3) O(2B) 3.33(2) no . . O(3) O(2B) 2.668(19) no . 2_546 O(3) O(31) 3.266(12) no . . O(3) O(52) 3.325(10) no . 4_565 O(3) C(12) 3.307(12) no . 2_556 O(3) C(13) 3.442(13) no . 2_556 O(3B) O(2B) 2.56(3) no . . O(3B) O(3C) 2.33(3) no . . O(3B) O(31) 3.524(19) no . . O(3B) O(52) 3.021(18) no . 4_565 O(3B) C(15) 3.458(19) no . 3_566 O(3B) C(16) 3.33(2) no . 3_566 O(3B) C(31) 3.50(2) no . . O(3C) O(2) 3.55(3) no . . O(3C) O(2) 2.80(3) no . 2_546 O(3C) O(2B) 2.03(3) no . 2_546 O(3C) O(3B) 2.33(3) no . . O(3C) O(31) 3.100(18) no . . O(3C) O(51) 3.546(17) no . 2_646 O(3C) C(2) 3.56(2) no . . O(3C) C(12) 3.303(19) no . 2_556 O(31) O(3) 3.266(12) no . . O(31) O(3B) 3.524(19) no . . O(31) O(3C) 3.100(18) no . . O(51) O(3C) 3.546(17) no . 2_656 O(52) O(3) 3.325(10) no . 4_564 O(52) O(3B) 3.021(18) no . 4_564 C(2) O(3C) 3.56(2) no . . C(12) O(3) 3.307(12) no . 2_546 C(12) O(3C) 3.303(19) no . 2_546 C(13) O(3) 3.442(13) no . 2_546 C(15) O(3B) 3.458(19) no . 3_566 C(16) O(2) 3.456(16) no . 3_566 C(16) O(3B) 3.33(2) no . 3_566 C(31) O(3B) 3.50(2) no . . Cu(1) H(1) 3.2598 no . 2_656 Cu(1) H(5) 2.9067 no . 4_655 Cu(1) H(8) 2.9664 no . 4_655 O(1) H(1) 3.0051 no . . O(1) H(4) 2.2468 no . . O(1) H(6) 3.4456 no . 3_566 O(1) H(7) 2.5021 no . . O(31) H(2) 2.4069 no . . O(31) H(3) 3.0737 no . 2_646 O(31) H(8) 2.5170 no . 4_655 O(32) H(1) 2.1197 no . 2_656 O(32) H(2) 2.6297 no . 2_656 O(32) H(3) 2.5831 no . . O(32) H(6) 2.5662 no . 2_656 O(32) H(8) 3.2944 no . 4_655 O(51) H(3) 2.5577 no . . O(51) H(5) 2.4568 no . 1_665 O(52) H(1) 2.9882 no . 3_666 O(52) H(4) 2.4905 no . . O(52) H(5) 2.9473 no . 3_566 N(1) H(2) 2.5270 no . . N(1) H(4) 2.6785 no . . N(1) H(6) 2.6503 no . . N(11) H(6) 3.2184 no . . N(11) H(7) 3.2153 no . . C(1) H(4) 3.3648 no . 3_666 C(2) H(1) 2.4844 no . . C(2) H(3) 3.2509 no . . C(2) H(4) 3.2533 no . . C(4) H(2) 3.2438 no . . C(4) H(4) 3.2721 no . . C(4) H(8) 3.4715 no . 3_566 C(5) H(4) 3.4846 no . 3_666 C(6) H(1) 3.2101 no . . C(6) H(2) 3.2482 no . . C(6) H(3) 3.2715 no . . C(6) H(4) 3.0916 no . 3_666 C(11) H(4) 2.7651 no . . C(11) H(6) 2.7377 no . . C(11) H(7) 2.6118 no . . C(12) H(4) 3.5232 no . 3_566 C(12) H(8) 3.1486 no . . C(13) H(1) 2.5501 no . . C(13) H(4) 3.3277 no . 3_566 C(13) H(7) 3.2279 no . . C(14) H(1) 2.4710 no . . C(14) H(4) 3.5366 no . 3_566 C(14) H(5) 3.2206 no . . C(14) H(8) 3.2231 no . . C(15) H(5) 3.5656 no . 3_556 C(15) H(6) 3.2290 no . . C(16) H(5) 3.1488 no . . C(16) H(5) 3.4582 no . 3_556 C(31) H(1) 3.1928 no . 2_656 C(31) H(2) 2.6379 no . . C(31) H(2) 3.4021 no . 2_656 C(31) H(3) 2.6721 no . . C(31) H(8) 2.8824 no . 4_655 C(51) H(1) 3.3989 no . 3_666 C(51) H(3) 2.6465 no . . C(51) H(4) 2.6104 no . . C(51) H(5) 3.3458 no . 3_566 H(1) H(2) 2.3022 no . . H(1) H(4) 3.5032 no . . H(1) H(6) 2.0954 no . . H(2) H(3) 2.9994 no . 2_646 H(3) H(7) 3.5481 no . 3_666 H(4) H(4) 3.1827 no . 3_666 H(4) H(6) 3.5550 no . 3_566 H(5) H(6) 2.3041 no . . H(7) H(8) 2.2981 no . . O(2) H(4) 3.5386 no . 4_565 O(2) H(6) 3.1865 no . 2_556 O(2) H(7) 3.2154 no . 3_566 O(2) H(8) 2.7658 no . 3_566 O(2B) H(1) 3.4230 no . 2_556 O(2B) H(2) 3.2973 no . 2_556 O(2B) H(6) 3.1777 no . 2_556 O(2B) H(7) 3.5355 no . 3_566 O(2B) H(7) 3.2397 no . 4_565 O(2B) H(8) 3.3455 no . 3_566 O(3) H(2) 3.5230 no . . O(3) H(5) 2.6435 no . 2_556 O(3) H(6) 2.9340 no . 2_556 O(3) H(7) 2.8493 no . 3_566 O(3) H(8) 3.5977 no . 3_566 O(3B) H(4) 3.5517 no . 4_565 O(3B) H(5) 3.5078 no . 2_556 O(3B) H(6) 3.3411 no . 2_556 O(3B) H(7) 2.9178 no . 3_566 O(3B) H(8) 2.6339 no . 3_566 O(3C) H(2) 3.1139 no . . O(3C) H(3) 3.4836 no . 2_646 O(3C) H(5) 2.4916 no . 2_556 O(3C) H(6) 3.2678 no . 2_556 O(3C) H(7) 3.2023 no . 3_566 H(1) O(2B) 3.4230 no . 2_546 H(2) O(2B) 3.2973 no . 2_546 H(2) O(3) 3.5230 no . . H(2) O(3C) 3.1139 no . . H(3) O(3C) 3.4836 no . 2_656 H(4) O(2) 3.5386 no . 4_564 H(4) O(3B) 3.5517 no . 4_564 H(5) O(3) 2.6435 no . 2_546 H(5) O(3B) 3.5078 no . 2_546 H(5) O(3C) 2.4916 no . 2_546 H(6) O(2) 3.1865 no . 2_546 H(6) O(2B) 3.1777 no . 2_546 H(6) O(3) 2.9340 no . 2_546 H(6) O(3B) 3.3411 no . 2_546 H(6) O(3C) 3.2678 no . 2_546 H(7) O(2) 3.2154 no . 3_566 H(7) O(2B) 3.5355 no . 3_566 H(7) O(2B) 3.2397 no . 4_564 H(7) O(3) 2.8493 no . 3_566 H(7) O(3B) 2.9178 no . 3_566 H(7) O(3C) 3.2023 no . 3_566 H(8) O(2) 2.7658 no . 3_566 H(8) O(2B) 3.3455 no . 3_566 H(8) O(3) 3.5977 no . 3_566 H(8) O(3B) 2.6339 no . 3_566 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N(1) H(1) O(32) . . 2_646 2.954(4) 0.860 2.120 163.3 no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data_1_b _database_code_depnum_ccdc_archive 'CCDC 787828' #TrackingRef '- CC-COM-10-2010-004689-rev.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 Cu N2 O7' _chemical_formula_weight 383.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 8.4048(12) _cell_length_b 10.2379(15) _cell_length_c 17.7707(18) _cell_angle_alpha 90.00 _cell_angle_beta 104.405(5) _cell_angle_gamma 90.00 _cell_volume 1481.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1782 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 25.57 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.721 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 1.517 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7513 _exptl_absorpt_correction_T_max 0.8390 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7435 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_sigmaI/netI 0.0638 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2752 _reflns_number_gt 2283 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0673P)^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 2752 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1335 _refine_ls_wR_factor_gt 0.1277 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 0.60575(6) 1.05774(5) 0.93204(3) 0.0211(2) Uani 1 1 d . . . C1 C 0.5201(5) 1.1108(4) 0.6976(2) 0.0201(9) Uani 1 1 d . . . C2 C 0.5606(5) 1.2028(4) 0.6493(2) 0.0214(10) Uani 1 1 d . . . H13A H 0.6327 1.2703 0.6696 0.026 Uiso 1 1 calc R . . C3 C 0.4927(5) 1.1941(4) 0.5697(2) 0.0191(9) Uani 1 1 d . . . C4 C 0.3837(5) 1.0944(4) 0.5381(2) 0.0202(9) Uani 1 1 d . . . H12A H 0.3392 1.0892 0.4848 0.024 Uiso 1 1 calc R . . C5 C 0.3427(5) 1.0027(4) 0.5882(2) 0.0190(9) Uani 1 1 d . . . C6 C 0.4119(5) 1.0111(4) 0.6667(2) 0.0226(10) Uani 1 1 d . . . H9A H 0.3856 0.9488 0.6998 0.027 Uiso 1 1 calc R . . C7 C 0.5892(5) 1.1191(4) 0.7839(2) 0.0221(10) Uani 1 1 d . . . C8 C 0.5304(5) 1.2929(4) 0.5166(2) 0.0199(9) Uani 1 1 d . . . C9 C 0.1320(5) 0.8829(4) 0.4912(2) 0.0231(10) Uani 1 1 d . . . C10 C 0.0169(5) 0.7683(4) 0.4811(2) 0.0218(9) Uani 1 1 d . . . C11 C -0.0583(5) 0.7303(5) 0.4054(2) 0.0287(11) Uani 1 1 d . . . H23A H -0.0305 0.7711 0.3637 0.034 Uiso 1 1 calc R . . C12 C -0.1724(5) 0.6335(5) 0.3926(2) 0.0276(11) Uani 1 1 d . . . H15A H -0.2216 0.6090 0.3418 0.033 Uiso 1 1 calc R . . C13 C -0.1423(5) 0.6074(4) 0.5237(2) 0.0235(10) Uani 1 1 d . . . H18A H -0.1710 0.5644 0.5645 0.028 Uiso 1 1 calc R . . C14 C -0.0261(5) 0.7041(4) 0.5407(2) 0.0239(10) Uani 1 1 d . . . H21A H 0.0228 0.7258 0.5921 0.029 Uiso 1 1 calc R . . N1 N -0.2161(4) 0.5722(4) 0.4510(2) 0.0222(8) Uani 1 1 d . . . N2 N 0.2335(4) 0.8984(4) 0.5627(2) 0.0236(8) Uani 1 1 d . . . H2A H 0.2312 0.8381 0.5961 0.028 Uiso 1 1 d R . . O1 O 0.5305(4) 1.0362(3) 0.82362(15) 0.0246(7) Uani 1 1 d . . . O2 O 0.6936(4) 1.2007(3) 0.81250(17) 0.0321(8) Uani 1 1 d . . . O3 O 0.4745(3) 1.2840(3) 0.44418(16) 0.0252(7) Uani 1 1 d . . . O4 O 0.6208(4) 1.3906(3) 0.54172(16) 0.0295(8) Uani 1 1 d . . . O5 O 0.1271(4) 0.9573(3) 0.43745(17) 0.0419(10) Uani 1 1 d . . . O1WA O 0.8371(10) 0.8796(15) 0.2049(4) 0.199(7) Uani 0.78 1 d P . . O2WA O 0.918(2) 0.5815(17) 0.2124(6) 0.266(11) Uani 0.78 1 d P . . O1WB O 0.7551(19) 0.717(2) 0.2100(8) 0.049(5) Uani 0.22 1 d P . . O2WB O 1.025(3) 0.566(3) 0.2011(13) 0.064(7) Uani 0.22 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0279(3) 0.0210(3) 0.0136(3) 0.0003(2) 0.0035(2) 0.0080(2) C1 0.022(2) 0.020(2) 0.018(2) -0.0029(18) 0.0036(17) -0.0021(18) C2 0.024(2) 0.020(2) 0.018(2) -0.0034(18) 0.0017(17) -0.0036(18) C3 0.021(2) 0.019(2) 0.018(2) 0.0003(18) 0.0062(17) -0.0007(18) C4 0.023(2) 0.021(2) 0.015(2) 0.0004(18) 0.0010(17) -0.0016(18) C5 0.022(2) 0.018(2) 0.016(2) 0.0018(18) 0.0032(17) -0.0026(18) C6 0.029(2) 0.020(2) 0.019(2) 0.0039(19) 0.0059(18) -0.0017(19) C7 0.025(2) 0.020(2) 0.021(2) -0.0025(19) 0.0048(18) 0.0091(19) C8 0.020(2) 0.023(2) 0.017(2) -0.0023(18) 0.0045(17) 0.0012(19) C9 0.022(2) 0.021(2) 0.025(2) -0.001(2) 0.0041(18) -0.0031(19) C10 0.019(2) 0.020(2) 0.025(2) 0.0000(19) 0.0024(17) -0.0009(18) C11 0.033(3) 0.034(3) 0.018(2) 0.002(2) 0.0065(19) -0.012(2) C12 0.031(3) 0.034(3) 0.017(2) -0.001(2) 0.0055(19) -0.010(2) C13 0.026(2) 0.024(2) 0.020(2) 0.0052(19) 0.0048(18) -0.0001(19) C14 0.025(2) 0.027(3) 0.018(2) -0.0008(19) 0.0009(18) -0.0032(19) N1 0.0230(19) 0.022(2) 0.0202(19) 0.0001(16) 0.0036(15) -0.0069(16) N2 0.027(2) 0.022(2) 0.0199(19) 0.0029(16) 0.0016(15) -0.0080(16) O1 0.0348(18) 0.0253(18) 0.0119(15) 0.0015(13) 0.0024(13) -0.0002(14) O2 0.0361(18) 0.034(2) 0.0213(16) -0.0056(15) -0.0020(14) -0.0100(16) O3 0.0318(17) 0.0251(18) 0.0174(15) 0.0014(13) 0.0036(12) -0.0118(14) O4 0.0400(18) 0.0300(19) 0.0157(15) 0.0009(14) 0.0014(13) -0.0178(15) O5 0.053(2) 0.043(2) 0.0218(18) 0.0097(16) -0.0069(16) -0.0262(18) O1WA 0.094(6) 0.47(2) 0.039(4) -0.005(8) 0.022(4) 0.045(9) O2WA 0.38(2) 0.36(2) 0.074(7) -0.098(10) 0.086(11) -0.24(2) O1WB 0.041(10) 0.091(16) 0.016(8) 0.021(9) 0.008(7) 0.036(10) O2WB 0.054(12) 0.098(18) 0.052(14) -0.012(12) 0.035(10) -0.028(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 1.885(3) . ? Cu1 N1 1.969(3) 4_676 ? Cu1 O4 1.993(3) 4_586 ? Cu1 O3 2.002(3) 4_586 ? Cu1 C8 2.339(4) 4_586 ? Cu1 O4 2.685(4) 2_646 ? C1 C2 1.373(6) . ? C1 C6 1.387(6) . ? C1 C7 1.502(5) . ? C2 C3 1.391(5) . ? C2 H13A 0.9300 . ? C3 C4 1.392(6) . ? C3 C8 1.470(6) . ? C4 C5 1.395(6) . ? C4 H12A 0.9300 . ? C5 C6 1.375(5) . ? C5 N2 1.407(5) . ? C6 H9A 0.9300 . ? C7 O2 1.226(5) . ? C7 O1 1.278(5) . ? C8 O3 1.258(5) . ? C8 O4 1.269(5) . ? C8 Cu1 2.339(4) 4_585 ? C9 O5 1.215(5) . ? C9 N2 1.351(5) . ? C9 C10 1.502(6) . ? C10 C14 1.370(6) . ? C10 C11 1.391(6) . ? C11 C12 1.359(6) . ? C11 H23A 0.9300 . ? C12 N1 1.339(5) . ? C12 H15A 0.9300 . ? C13 N1 1.336(5) . ? C13 C14 1.370(6) . ? C13 H18A 0.9300 . ? C14 H21A 0.9300 . ? N1 Cu1 1.969(3) 4_475 ? N2 H2A 0.8603 . ? O3 Cu1 2.002(3) 4_585 ? O4 Cu1 1.993(3) 4_585 ? O4 Cu1 2.685(3) 2_656 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N1 98.24(14) . 4_676 ? O1 Cu1 O4 162.55(13) . 4_586 ? N1 Cu1 O4 98.71(13) 4_676 4_586 ? O1 Cu1 O3 98.68(12) . 4_586 ? N1 Cu1 O3 160.87(14) 4_676 4_586 ? O4 Cu1 O3 65.32(12) 4_586 4_586 ? O1 Cu1 C8 131.09(13) . 4_586 ? N1 Cu1 C8 130.39(14) 4_676 4_586 ? O4 Cu1 C8 32.84(12) 4_586 4_586 ? O3 Cu1 C8 32.54(12) 4_586 4_586 ? O1 Cu1 O4 91.77(11) . 2_646 ? N1 Cu1 O4 94.69(13) 4_676 2_646 ? O4 Cu1 O4 82.77(13) 4_586 2_646 ? O3 Cu1 O4 93.63(11) 4_586 2_646 ? C8 Cu1 O4 89.32(12) 4_586 2_646 ? O1 Cu1 Cu1 124.09(10) . 3_677 ? N1 Cu1 Cu1 98.47(11) 4_676 3_677 ? O4 Cu1 Cu1 48.81(10) 4_586 3_677 ? O3 Cu1 Cu1 79.22(9) 4_586 3_677 ? C8 Cu1 Cu1 61.18(10) 4_586 3_677 ? O4 Cu1 Cu1 33.96(6) 2_646 3_677 ? C2 C1 C6 119.9(4) . . ? C2 C1 C7 120.5(4) . . ? C6 C1 C7 119.6(4) . . ? C1 C2 C3 119.3(4) . . ? C1 C2 H13A 120.4 . . ? C3 C2 H13A 120.4 . . ? C2 C3 C4 121.3(4) . . ? C2 C3 C8 120.6(4) . . ? C4 C3 C8 118.1(4) . . ? C3 C4 C5 118.6(4) . . ? C3 C4 H12A 120.7 . . ? C5 C4 H12A 120.7 . . ? C6 C5 C4 119.7(4) . . ? C6 C5 N2 116.9(4) . . ? C4 C5 N2 123.4(4) . . ? C5 C6 C1 121.2(4) . . ? C5 C6 H9A 119.4 . . ? C1 C6 H9A 119.4 . . ? O2 C7 O1 123.9(4) . . ? O2 C7 C1 121.1(4) . . ? O1 C7 C1 115.0(4) . . ? O3 C8 O4 117.1(4) . . ? O3 C8 C3 121.4(4) . . ? O4 C8 C3 121.5(4) . . ? O3 C8 Cu1 58.9(2) . 4_585 ? O4 C8 Cu1 58.4(2) . 4_585 ? C3 C8 Cu1 176.3(3) . 4_585 ? O5 C9 N2 123.7(4) . . ? O5 C9 C10 120.1(4) . . ? N2 C9 C10 116.2(4) . . ? C14 C10 C11 118.0(4) . . ? C14 C10 C9 124.6(4) . . ? C11 C10 C9 117.3(4) . . ? C12 C11 C10 119.9(4) . . ? C12 C11 H23A 120.1 . . ? C10 C11 H23A 120.1 . . ? N1 C12 C11 122.0(4) . . ? N1 C12 H15A 119.0 . . ? C11 C12 H15A 119.0 . . ? N1 C13 C14 122.9(4) . . ? N1 C13 H18A 118.6 . . ? C14 C13 H18A 118.6 . . ? C10 C14 C13 119.1(4) . . ? C10 C14 H21A 120.5 . . ? C13 C14 H21A 120.5 . . ? C13 N1 C12 118.2(4) . . ? C13 N1 Cu1 119.9(3) . 4_475 ? C12 N1 Cu1 121.8(3) . 4_475 ? C9 N2 C5 126.9(4) . . ? C9 N2 H2A 116.6 . . ? C5 N2 H2A 116.5 . . ? C7 O1 Cu1 114.1(3) . . ? C8 O3 Cu1 88.6(2) . 4_585 ? C8 O4 Cu1 88.7(2) . 4_585 ? C8 O4 Cu1 100.1(3) . 2_656 ? Cu1 O4 Cu1 97.23(12) 4_585 2_656 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.982 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.108 data_1c _database_code_depnum_ccdc_archive 'CCDC 787829' #TrackingRef '- CC-COM-10-2010-004689-rev.cif' _audit_creation_date 2010-04-15 _audit_creation_method SHELXL-97 _publ_section_references ; Rigaku Americas and Rigaku Corporation. (2007). CrystalStructure (Version 3.8). Single Crystal Structure Analysis Software. Rigaku Americas, 9009 TX, USA 77381-5209. Rigaku, Tokyo 196-8666, Japan. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M., Polidori, G., and Camalli, M. (1994) J. Appl. Cryst., 27, 435. SIR92 Sheldrick, G.M. (1997). SHELXL97. University of Gottingen, Germany. ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H8 Cu N2 O5 ' _chemical_formula_sum 'C14 H8 Cu N2 O5' _chemical_formula_weight 347.76 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 8.497(5) _cell_length_b 10.296(4) _cell_length_c 17.749(7) _cell_angle_alpha 90.00 _cell_angle_beta 104.624(18) _cell_angle_gamma 90.00 _cell_volume 1502.4(12) _cell_formula_units_Z 4 _cell_measurement_temperature 453(1) _cell_measurement_reflns_used 10654 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 700 _exptl_absorpt_coefficient_mu 1.477 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8088 _exptl_absorpt_correction_T_max 0.8088 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 453(1) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source ; MicroMax-007HF microfocus rotating anode X-ray generator ; _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 13698 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3435 _reflns_number_gt 2895 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'RAPID AUTO (Rigaku, 1998)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SIR92 (Altomare, et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_publication_material 'CrystalStructure 3.8 (Rigaku, 2007)' _computing_molecular_graphics 'CrystalStructure 3.8' _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^)+(0.0622P)^2^+0.9639P] 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 3435 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1145 _refine_ls_wR_factor_gt 0.1087 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 1.11185(4) 0.44452(3) 0.932156(17) 0.03760(13) Uani 1 1 d . . . O1 O 0.6230(3) 0.5374(2) 0.43638(12) 0.0613(7) Uani 1 1 d . . . O31 O 1.0439(3) 0.46603(18) 0.82341(10) 0.0455(5) Uani 1 1 d . . . O32 O 1.1962(3) 0.2954(2) 0.81257(11) 0.0541(5) Uani 1 1 d . . . O51 O 1.1280(3) 0.1099(2) 0.54192(11) 0.0521(5) Uani 1 1 d . . . O52 O 0.9771(2) 0.21097(18) 0.44327(10) 0.0449(5) Uani 1 1 d . . . N1 N 0.7379(3) 0.5975(2) 0.56136(12) 0.0392(5) Uani 1 1 d . . . H1 H 0.7385 0.6590 0.5942 0.047 Uiso 1 1 calc R . . N11 N 0.2878(3) 0.9229(2) 0.45262(13) 0.0384(5) Uani 1 1 d . . . C1 C 0.8466(3) 0.4940(2) 0.58708(14) 0.0330(5) Uani 1 1 d . . . C2 C 0.9166(3) 0.4859(3) 0.66684(14) 0.0372(5) Uani 1 1 d . . . H2 H 0.8905 0.5476 0.7000 0.045 Uiso 1 1 calc R . . C3 C 1.0251(3) 0.3866(2) 0.69760(13) 0.0346(5) Uani 1 1 d . . . C4 C 1.0652(3) 0.2942(2) 0.64858(14) 0.0356(5) Uani 1 1 d . . . H3 H 1.1373 0.2274 0.6687 0.043 Uiso 1 1 calc R . . C5 C 0.9956(3) 0.3033(2) 0.56881(14) 0.0325(5) Uani 1 1 d . . . C6 C 0.8871(3) 0.4020(2) 0.53730(14) 0.0332(5) Uani 1 1 d . . . H4 H 0.8421 0.4066 0.4839 0.040 Uiso 1 1 calc R . . C11 C 0.6325(3) 0.6107(3) 0.49066(15) 0.0386(6) Uani 1 1 d . . . C12 C 0.3596(3) 0.8866(3) 0.52507(15) 0.0418(6) Uani 1 1 d . . . H5 H 0.3314 0.9288 0.5661 0.050 Uiso 1 1 calc R . . C13 C 0.4749(3) 0.7885(3) 0.54180(15) 0.0422(6) Uani 1 1 d . . . H6 H 0.5220 0.7651 0.5931 0.051 Uiso 1 1 calc R . . C14 C 0.5189(3) 0.7261(2) 0.48153(15) 0.0373(6) Uani 1 1 d . . . C15 C 0.4441(4) 0.7644(3) 0.40620(16) 0.0515(7) Uani 1 1 d . . . H7 H 0.4711 0.7245 0.3641 0.062 Uiso 1 1 calc R . . C16 C 0.3303(4) 0.8615(3) 0.39409(16) 0.0519(7) Uani 1 1 d . . . H8 H 0.2804 0.8858 0.3432 0.062 Uiso 1 1 calc R . . C31 C 1.0959(3) 0.3793(2) 0.78427(14) 0.0368(5) Uani 1 1 d . . . C51 C 1.0355(3) 0.2052(2) 0.51571(14) 0.0344(5) 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 0.0490(2) 0.0361(2) 0.02714(18) -0.00078(11) 0.00840(13) -0.01205(13) O1 0.0701(16) 0.0589(14) 0.0431(12) -0.0145(10) -0.0076(11) 0.0285(11) O31 0.0634(13) 0.0438(10) 0.0262(9) -0.0029(8) 0.0058(8) -0.0019(9) O32 0.0632(13) 0.0555(12) 0.0361(10) 0.0091(9) -0.0012(9) 0.0118(10) O51 0.0716(14) 0.0484(11) 0.0324(9) -0.0028(9) 0.0061(9) 0.0298(10) O52 0.0603(12) 0.0448(10) 0.0277(8) -0.0009(8) 0.0079(8) 0.0191(9) N1 0.0424(12) 0.0334(10) 0.0365(11) -0.0057(9) 0.0003(9) 0.0107(9) N11 0.0391(12) 0.0375(11) 0.0371(11) 0.0022(9) 0.0067(9) 0.0091(9) C1 0.0340(12) 0.0303(11) 0.0335(12) 0.0005(10) 0.0064(9) 0.0057(10) C2 0.0446(14) 0.0342(12) 0.0310(12) -0.0039(10) 0.0060(10) 0.0049(11) C3 0.0421(13) 0.0323(12) 0.0271(11) -0.0009(9) 0.0043(9) 0.0002(10) C4 0.0414(13) 0.0317(11) 0.0316(12) 0.0027(10) 0.0056(10) 0.0077(10) C5 0.0351(12) 0.0316(11) 0.0302(11) -0.0010(9) 0.0074(9) 0.0032(9) C6 0.0369(13) 0.0337(12) 0.0271(11) -0.0015(10) 0.0048(9) 0.0040(10) C11 0.0388(14) 0.0348(12) 0.0396(13) 0.0001(11) 0.0050(10) 0.0071(10) C12 0.0442(15) 0.0424(14) 0.0379(13) -0.0068(11) 0.0086(11) 0.0095(12) C13 0.0426(14) 0.0453(14) 0.0342(12) -0.0014(11) 0.0015(10) 0.0102(11) C14 0.0349(13) 0.0351(13) 0.0391(13) -0.0005(10) 0.0041(10) 0.0042(10) C15 0.0614(18) 0.0563(17) 0.0376(14) 0.0007(13) 0.0139(13) 0.0235(15) C16 0.0627(19) 0.0584(18) 0.0340(13) 0.0062(13) 0.0113(12) 0.0242(15) C31 0.0439(14) 0.0359(12) 0.0282(12) 0.0014(10) 0.0047(10) -0.0077(11) C51 0.0382(13) 0.0324(12) 0.0320(12) -0.0017(10) 0.0078(10) 0.0053(10) _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 O31 1.883(2) . ? Cu1 N11 1.989(2) 4_676 ? Cu1 O51 1.998(2) 4_566 ? Cu1 O52 2.0067(19) 4_566 ? Cu1 C51 2.341(2) 4_566 ? O1 C11 1.210(3) . ? O31 C31 1.277(3) . ? O32 C31 1.229(3) . ? O51 C51 1.270(3) . ? O51 Cu1 1.998(2) 4_565 ? O52 C51 1.257(3) . ? O52 Cu1 2.0067(19) 4_565 ? N1 C11 1.352(3) . ? N1 C1 1.408(3) . ? N1 H1 0.8600 . ? N11 C12 1.330(3) . ? N11 C16 1.341(4) . ? N11 Cu1 1.989(2) 4_475 ? C1 C2 1.393(3) . ? C1 C6 1.396(4) . ? C2 C3 1.392(4) . ? C2 H2 0.9300 . ? C3 C4 1.389(4) . ? C3 C31 1.506(3) . ? C4 C5 1.393(3) . ? C4 H3 0.9300 . ? C5 C6 1.391(3) . ? C5 C51 1.479(3) . ? C6 H4 0.9300 . ? C11 C14 1.513(3) . ? C12 C13 1.386(4) . ? C12 H5 0.9300 . ? C13 C14 1.378(4) . ? C13 H6 0.9300 . ? C14 C15 1.385(4) . ? C15 C16 1.370(4) . ? C15 H7 0.9300 . ? C16 H8 0.9300 . ? C51 Cu1 2.341(2) 4_565 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O31 Cu1 N11 97.37(9) . 4_676 ? O31 Cu1 O51 163.78(9) . 4_566 ? N11 Cu1 O51 98.68(9) 4_676 4_566 ? O31 Cu1 O52 99.19(8) . 4_566 ? N11 Cu1 O52 161.95(9) 4_676 4_566 ? O51 Cu1 O52 65.22(7) 4_566 4_566 ? O31 Cu1 C51 131.64(9) . 4_566 ? N11 Cu1 C51 130.68(9) 4_676 4_566 ? O51 Cu1 C51 32.83(8) 4_566 4_566 ? O52 Cu1 C51 32.47(8) 4_566 4_566 ? C31 O31 Cu1 114.64(17) . . ? C51 O51 Cu1 88.60(15) . 4_565 ? C51 O52 Cu1 88.56(15) . 4_565 ? C11 N1 C1 127.1(2) . . ? C11 N1 H1 116.4 . . ? C1 N1 H1 116.4 . . ? C12 N11 C16 118.0(2) . . ? C12 N11 Cu1 120.62(18) . 4_475 ? C16 N11 Cu1 121.25(18) . 4_475 ? C2 C1 C6 119.5(2) . . ? C2 C1 N1 116.9(2) . . ? C6 C1 N1 123.7(2) . . ? C3 C2 C1 120.9(2) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C4 C3 C2 120.0(2) . . ? C4 C3 C31 120.5(2) . . ? C2 C3 C31 119.5(2) . . ? C3 C4 C5 118.8(2) . . ? C3 C4 H3 120.6 . . ? C5 C4 H3 120.6 . . ? C6 C5 C4 121.8(2) . . ? C6 C5 C51 118.6(2) . . ? C4 C5 C51 119.7(2) . . ? C5 C6 C1 119.0(2) . . ? C5 C6 H4 120.5 . . ? C1 C6 H4 120.5 . . ? O1 C11 N1 124.9(2) . . ? O1 C11 C14 119.4(2) . . ? N1 C11 C14 115.7(2) . . ? N11 C12 C13 122.6(2) . . ? N11 C12 H5 118.7 . . ? C13 C12 H5 118.7 . . ? C14 C13 C12 119.3(2) . . ? C14 C13 H6 120.4 . . ? C12 C13 H6 120.4 . . ? C13 C14 C15 117.9(2) . . ? C13 C14 C11 125.0(2) . . ? C15 C14 C11 116.8(2) . . ? C16 C15 C14 119.5(3) . . ? C16 C15 H7 120.2 . . ? C14 C15 H7 120.2 . . ? N11 C16 C15 122.7(3) . . ? N11 C16 H8 118.7 . . ? C15 C16 H8 118.7 . . ? O32 C31 O31 124.7(2) . . ? O32 C31 C3 120.7(2) . . ? O31 C31 C3 114.7(2) . . ? O52 C51 O51 117.4(2) . . ? O52 C51 C5 121.6(2) . . ? O51 C51 C5 121.0(2) . . ? O52 C51 Cu1 58.97(13) . 4_565 ? O51 C51 Cu1 58.57(13) . 4_565 ? C5 C51 Cu1 176.95(19) . 4_565 ? 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 N11 Cu1 O31 C31 101.4(2) 4_676 . . . ? O51 Cu1 O31 C31 -86.8(4) 4_566 . . . ? O52 Cu1 O31 C31 -71.4(2) 4_566 . . . ? C51 Cu1 O31 C31 -72.6(2) 4_566 . . . ? C11 N1 C1 C2 -165.8(3) . . . . ? C11 N1 C1 C6 14.5(4) . . . . ? C6 C1 C2 C3 -0.6(4) . . . . ? N1 C1 C2 C3 179.8(2) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? C1 C2 C3 C31 -178.8(2) . . . . ? C2 C3 C4 C5 0.3(4) . . . . ? C31 C3 C4 C5 179.2(2) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C3 C4 C5 C51 -179.4(2) . . . . ? C4 C5 C6 C1 -0.2(4) . . . . ? C51 C5 C6 C1 179.0(2) . . . . ? C2 C1 C6 C5 0.6(4) . . . . ? N1 C1 C6 C5 -179.8(2) . . . . ? C1 N1 C11 O1 -4.7(5) . . . . ? C1 N1 C11 C14 174.5(2) . . . . ? C16 N11 C12 C13 -0.3(4) . . . . ? Cu1 N11 C12 C13 175.6(2) 4_475 . . . ? N11 C12 C13 C14 0.6(4) . . . . ? C12 C13 C14 C15 -0.4(4) . . . . ? C12 C13 C14 C11 -174.9(3) . . . . ? O1 C11 C14 C13 155.7(3) . . . . ? N1 C11 C14 C13 -23.6(4) . . . . ? O1 C11 C14 C15 -18.9(4) . . . . ? N1 C11 C14 C15 161.8(3) . . . . ? C13 C14 C15 C16 -0.1(5) . . . . ? C11 C14 C15 C16 174.8(3) . . . . ? C12 N11 C16 C15 -0.3(5) . . . . ? Cu1 N11 C16 C15 -176.1(3) 4_475 . . . ? C14 C15 C16 N11 0.5(5) . . . . ? Cu1 O31 C31 O32 -7.7(4) . . . . ? Cu1 O31 C31 C3 172.71(17) . . . . ? C4 C3 C31 O32 3.6(4) . . . . ? C2 C3 C31 O32 -177.4(3) . . . . ? C4 C3 C31 O31 -176.8(2) . . . . ? C2 C3 C31 O31 2.1(4) . . . . ? Cu1 O52 C51 O51 -4.9(3) 4_565 . . . ? Cu1 O52 C51 C5 176.5(2) 4_565 . . . ? Cu1 O51 C51 O52 4.9(3) 4_565 . . . ? Cu1 O51 C51 C5 -176.5(2) 4_565 . . . ? C6 C5 C51 O52 1.8(4) . . . . ? C4 C5 C51 O52 -179.0(2) . . . . ? C6 C5 C51 O51 -176.8(3) . . . . ? C4 C5 C51 O51 2.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.522 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.103 data_1d _database_code_depnum_ccdc_archive 'CCDC 787830' #TrackingRef '- CC-COM-10-2010-004689-rev.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 Cu N2 O6' _chemical_formula_weight 379.82 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 8.4283(11) _cell_length_b 10.2553(13) _cell_length_c 17.8159(18) _cell_angle_alpha 90.00 _cell_angle_beta 104.408(5) _cell_angle_gamma 90.00 _cell_volume 1491.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4504 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 28.28 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 1.500 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7953 _exptl_absorpt_correction_T_max 0.8405 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7172 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_sigmaI/netI 0.0466 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.25 _reflns_number_total 2694 _reflns_number_gt 2486 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The atoms O1, C1, C2, C3, C4, C5, N1, O2, C6, C8, C9, and C10 were restrained in the refinement using SIMU and DELU instructions. The distances of C15-O6 and C15A-O6A were restrained using DFIX. The large R factors were caused by disordered methanol molecules. ; _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^)+(0.0631P)^2^+39.8085P] 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 2694 _refine_ls_number_parameters 216 _refine_ls_number_restraints 106 _refine_ls_R_factor_all 0.1321 _refine_ls_R_factor_gt 0.1262 _refine_ls_wR_factor_ref 0.2841 _refine_ls_wR_factor_gt 0.2813 _refine_ls_goodness_of_fit_ref 1.336 _refine_ls_restrained_S_all 1.314 _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 0.60603(16) -0.05776(12) -0.56792(7) 0.0149(4) Uani 1 1 d . . . O1 O 0.4747(9) -0.2150(7) -0.5557(4) 0.0181(13) Uani 1 1 d U . . O2 O 0.6209(10) -0.1087(7) -0.4585(4) 0.0210(13) Uani 1 1 d U . . O3 O 0.6936(10) -0.2994(8) -0.1874(4) 0.0285(19) Uani 1 1 d . . . O4 O 0.5307(10) -0.4637(7) -0.1764(4) 0.0196(17) Uani 1 1 d . . . O5 O 0.1273(11) -0.5415(9) -0.5621(5) 0.039(2) Uani 1 1 d . . . N1 N 0.2342(11) -0.6013(9) -0.4376(5) 0.0165(13) Uani 1 1 d U . . H1A H 0.2326 -0.6617 -0.4044 0.020 Uiso 1 1 calc R . . N2 N -0.2176(11) -0.9268(8) -0.5489(5) 0.0174(14) Uani 1 1 d U . . C1 C 0.5311(13) -0.2063(10) -0.4836(6) 0.0172(12) Uani 1 1 d U . . C2 C 0.4917(13) -0.3059(10) -0.4303(6) 0.0146(12) Uani 1 1 d U . . C3 C 0.5620(13) -0.2971(10) -0.3508(6) 0.0152(12) Uani 1 1 d U . . H3A H 0.6358 -0.2309 -0.3308 0.018 Uiso 1 1 calc R . . C4 C 0.5193(13) -0.3893(10) -0.3024(6) 0.0155(12) Uani 1 1 d U . . C5 C 0.4118(13) -0.4882(10) -0.3331(6) 0.0156(13) Uani 1 1 d U . . H5A H 0.3849 -0.5502 -0.3002 0.019 Uiso 1 1 calc R . . C6 C 0.3430(13) -0.4967(10) -0.4122(6) 0.0159(13) Uani 1 1 d U . . C7 C 0.3855(12) -0.4060(10) -0.4615(6) 0.014(2) Uani 1 1 d . . . H7A H 0.3433 -0.4123 -0.5148 0.016 Uiso 1 1 calc R . . C8 C 0.5897(13) -0.3806(10) -0.2166(6) 0.0155(15) Uani 1 1 d U . . C9 C 0.1324(13) -0.6166(10) -0.5086(6) 0.0162(14) Uani 1 1 d U . . C10 C 0.0178(13) -0.7321(10) -0.5191(6) 0.0149(16) Uani 1 1 d U . . C11 C -0.0579(14) -0.7687(12) -0.5949(6) 0.026(3) Uani 1 1 d . . . H11A H -0.0309 -0.7276 -0.6365 0.031 Uiso 1 1 calc R . . C12 C -0.1736(13) -0.8668(10) -0.6074(6) 0.0188(16) Uani 1 1 d U . . H12A H -0.2226 -0.8921 -0.6580 0.023 Uiso 1 1 calc R . . C13 C -0.0259(13) -0.7957(10) -0.4597(6) 0.019(2) Uani 1 1 d . . . H13A H 0.0228 -0.7734 -0.4085 0.022 Uiso 1 1 calc R . . C14 C -0.1417(13) -0.8925(10) -0.4758(6) 0.0175(16) Uani 1 1 d U . . H14A H -0.1688 -0.9359 -0.4349 0.021 Uiso 1 1 calc R . . O6 O -0.160(4) 0.377(3) -0.7949(18) 0.086(10) Uiso 0.50(3) 1 d PD A 1 C15 C -0.214(6) 0.245(3) -0.792(3) 0.098(16) Uiso 0.50(3) 1 d PD A 1 O6A O 0.009(5) 0.049(4) -0.786(2) 0.127(15) Uiso 0.50(3) 1 d PD A 2 C15A C -0.144(5) 0.112(5) -0.792(3) 0.098(16) Uiso 0.50(3) 1 d PD A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0236(7) 0.0131(7) 0.0072(6) -0.0001(5) 0.0025(5) -0.0106(5) O1 0.026(3) 0.015(3) 0.012(2) 0.001(2) 0.004(2) -0.011(2) O2 0.031(3) 0.019(3) 0.012(2) 0.000(2) 0.002(2) -0.011(2) O3 0.036(5) 0.033(5) 0.012(4) -0.004(3) -0.002(3) -0.008(4) O4 0.035(4) 0.017(4) 0.004(3) -0.003(3) 0.000(3) 0.000(3) O5 0.043(5) 0.045(6) 0.018(4) 0.011(4) -0.013(4) -0.027(5) N1 0.021(3) 0.014(3) 0.015(2) 0.002(2) 0.003(2) -0.005(2) N2 0.022(3) 0.011(3) 0.017(3) 0.001(2) 0.002(3) -0.009(3) C1 0.025(3) 0.016(2) 0.011(2) -0.0020(19) 0.005(2) -0.006(2) C2 0.021(3) 0.013(3) 0.011(2) -0.002(2) 0.007(2) -0.003(2) C3 0.022(3) 0.013(3) 0.012(2) -0.002(2) 0.005(2) -0.003(2) C4 0.022(3) 0.013(2) 0.012(2) -0.0001(19) 0.004(2) -0.001(2) C5 0.021(3) 0.014(3) 0.012(2) 0.002(2) 0.004(2) -0.003(2) C6 0.021(3) 0.014(3) 0.013(2) 0.001(2) 0.004(2) -0.004(2) C7 0.021(5) 0.010(5) 0.008(4) -0.001(4) 0.000(4) -0.004(4) C8 0.023(3) 0.013(3) 0.011(2) -0.001(2) 0.004(3) 0.001(3) C9 0.020(3) 0.013(3) 0.015(3) 0.001(2) 0.004(2) -0.004(2) C10 0.019(3) 0.012(3) 0.015(3) 0.000(3) 0.005(3) -0.003(3) C11 0.030(7) 0.035(7) 0.010(5) 0.000(5) 0.002(5) -0.009(5) C12 0.024(4) 0.014(4) 0.017(3) 0.002(3) 0.002(3) -0.011(3) C13 0.022(6) 0.018(6) 0.013(5) -0.004(4) -0.001(4) -0.001(4) C14 0.023(4) 0.012(3) 0.016(3) 0.000(3) 0.002(3) -0.007(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 O4 1.890(7) 4 ? Cu1 N2 1.969(8) 1_665 ? Cu1 O2 1.992(7) . ? Cu1 O1 1.998(7) . ? Cu1 C1 2.334(10) . ? Cu1 O2 2.692(8) 3_654 ? Cu1 C8 2.693(10) 4 ? O1 C1 1.257(13) . ? O2 C1 1.268(13) . ? O2 Cu1 2.692(8) 3_654 ? O3 C8 1.226(13) . ? O4 C8 1.291(13) . ? O4 Cu1 1.890(7) 4_556 ? O5 C9 1.217(13) . ? N1 C9 1.349(13) . ? N1 C6 1.411(14) . ? N1 H1A 0.8600 . ? N2 C12 1.340(13) . ? N2 C14 1.347(13) . ? N2 Cu1 1.969(8) 1_445 ? C1 C2 1.488(14) . ? C2 C7 1.384(14) . ? C2 C3 1.395(14) . ? C3 C4 1.386(14) . ? C3 H3A 0.9300 . ? C4 C5 1.380(15) . ? C4 C8 1.498(14) . ? C5 C6 1.387(14) . ? C5 H5A 0.9300 . ? C6 C7 1.386(15) . ? C7 H7A 0.9300 . ? C8 Cu1 2.693(10) 4_556 ? C9 C10 1.510(14) . ? C10 C13 1.371(15) . ? C10 C11 1.394(15) . ? C11 C12 1.380(16) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C14 1.371(15) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? O6 C15 1.432(10) . ? O6A C15A 1.420(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cu1 N2 98.3(3) 4 1_665 ? O4 Cu1 O2 162.6(3) 4 . ? N2 Cu1 O2 98.6(3) 1_665 . ? O4 Cu1 O1 98.7(3) 4 . ? N2 Cu1 O1 161.2(3) 1_665 . ? O2 Cu1 O1 65.4(3) . . ? O4 Cu1 C1 131.1(3) 4 . ? N2 Cu1 C1 130.4(4) 1_665 . ? O2 Cu1 C1 32.9(3) . . ? O1 Cu1 C1 32.6(3) . . ? O4 Cu1 O2 91.9(3) 4 3_654 ? N2 Cu1 O2 94.4(3) 1_665 3_654 ? O2 Cu1 O2 82.5(3) . 3_654 ? O1 Cu1 O2 93.2(3) . 3_654 ? C1 Cu1 O2 89.1(3) . 3_654 ? O4 Cu1 C8 25.9(3) 4 4 ? N2 Cu1 C8 100.4(3) 1_665 4 ? O2 Cu1 C8 151.2(3) . 4 ? O1 Cu1 C8 91.3(3) . 4 ? C1 Cu1 C8 121.6(3) . 4 ? O2 Cu1 C8 117.2(3) 3_654 4 ? C1 O1 Cu1 88.6(6) . . ? C1 O2 Cu1 88.6(6) . . ? C1 O2 Cu1 100.0(7) . 3_654 ? Cu1 O2 Cu1 97.5(3) . 3_654 ? C8 O4 Cu1 114.4(6) . 4_556 ? C9 N1 C6 126.9(9) . . ? C9 N1 H1A 116.6 . . ? C6 N1 H1A 116.6 . . ? C12 N2 C14 118.4(9) . . ? C12 N2 Cu1 121.5(7) . 1_445 ? C14 N2 Cu1 120.1(7) . 1_445 ? O1 C1 O2 117.2(9) . . ? O1 C1 C2 121.1(9) . . ? O2 C1 C2 121.6(9) . . ? O1 C1 Cu1 58.8(5) . . ? O2 C1 Cu1 58.5(5) . . ? C2 C1 Cu1 176.6(8) . . ? C7 C2 C3 121.6(9) . . ? C7 C2 C1 118.5(9) . . ? C3 C2 C1 119.9(9) . . ? C4 C3 C2 118.5(10) . . ? C4 C3 H3A 120.7 . . ? C2 C3 H3A 120.7 . . ? C5 C4 C3 120.1(9) . . ? C5 C4 C8 120.2(9) . . ? C3 C4 C8 119.7(9) . . ? C4 C5 C6 121.1(10) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C7 C6 C5 119.5(10) . . ? C7 C6 N1 123.8(9) . . ? C5 C6 N1 116.6(9) . . ? C2 C7 C6 119.1(9) . . ? C2 C7 H7A 120.4 . . ? C6 C7 H7A 120.4 . . ? O3 C8 O4 123.1(9) . . ? O3 C8 C4 122.2(9) . . ? O4 C8 C4 114.7(9) . . ? O3 C8 Cu1 83.4(6) . 4_556 ? O4 C8 Cu1 39.7(4) . 4_556 ? C4 C8 Cu1 154.1(7) . 4_556 ? O5 C9 N1 123.4(10) . . ? O5 C9 C10 120.2(9) . . ? N1 C9 C10 116.4(9) . . ? C13 C10 C11 118.3(10) . . ? C13 C10 C9 124.4(9) . . ? C11 C10 C9 117.1(9) . . ? C12 C11 C10 119.2(10) . . ? C12 C11 H11A 120.4 . . ? C10 C11 H11A 120.4 . . ? N2 C12 C11 122.1(10) . . ? N2 C12 H12A 119.0 . . ? C11 C12 H12A 119.0 . . ? C10 C13 C14 119.8(10) . . ? C10 C13 H13A 120.1 . . ? C14 C13 H13A 120.1 . . ? N2 C14 C13 122.3(10) . . ? N2 C14 H14A 118.9 . . ? C13 C14 H14A 118.9 . . ? 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 O4 Cu1 O1 C1 -175.6(6) 4 . . . ? N2 Cu1 O1 C1 30.4(14) 1_665 . . . ? O2 Cu1 O1 C1 -3.0(6) . . . . ? O2 Cu1 O1 C1 -83.2(6) 3_654 . . . ? C8 Cu1 O1 C1 159.5(7) 4 . . . ? O4 Cu1 O2 C1 28.0(14) 4 . . . ? N2 Cu1 O2 C1 -166.7(7) 1_665 . . . ? O1 Cu1 O2 C1 2.9(6) . . . . ? O2 Cu1 O2 C1 99.9(7) 3_654 . . . ? C8 Cu1 O2 C1 -35.8(10) 4 . . . ? O4 Cu1 O2 Cu1 -72.0(11) 4 . . 3_654 ? N2 Cu1 O2 Cu1 93.3(3) 1_665 . . 3_654 ? O1 Cu1 O2 Cu1 -97.0(3) . . . 3_654 ? C1 Cu1 O2 Cu1 -99.9(7) . . . 3_654 ? O2 Cu1 O2 Cu1 0.0 3_654 . . 3_654 ? C8 Cu1 O2 Cu1 -135.8(6) 4 . . 3_654 ? Cu1 O1 C1 O2 4.8(10) . . . . ? Cu1 O1 C1 C2 -176.0(9) . . . . ? Cu1 O2 C1 O1 -4.8(10) . . . . ? Cu1 O2 C1 O1 92.6(10) 3_654 . . . ? Cu1 O2 C1 C2 176.0(10) . . . . ? Cu1 O2 C1 C2 -86.6(10) 3_654 . . . ? Cu1 O2 C1 Cu1 97.4(3) 3_654 . . . ? O4 Cu1 C1 O1 5.8(9) 4 . . . ? N2 Cu1 C1 O1 -167.6(6) 1_665 . . . ? O2 Cu1 C1 O1 175.0(10) . . . . ? O2 Cu1 C1 O1 97.4(6) 3_654 . . . ? C8 Cu1 C1 O1 -24.3(8) 4 . . . ? O4 Cu1 C1 O2 -169.2(6) 4 . . . ? N2 Cu1 C1 O2 17.3(9) 1_665 . . . ? O1 Cu1 C1 O2 -175.0(10) . . . . ? O2 Cu1 C1 O2 -77.6(6) 3_654 . . . ? C8 Cu1 C1 O2 160.7(6) 4 . . . ? O4 Cu1 C1 C2 96(13) 4 . . . ? N2 Cu1 C1 C2 -77(13) 1_665 . . . ? O2 Cu1 C1 C2 -94(13) . . . . ? O1 Cu1 C1 C2 91(13) . . . . ? O2 Cu1 C1 C2 -172(13) 3_654 . . . ? C8 Cu1 C1 C2 66(13) 4 . . . ? O1 C1 C2 C7 -2.7(16) . . . . ? O2 C1 C2 C7 176.5(10) . . . . ? Cu1 C1 C2 C7 -91(13) . . . . ? O1 C1 C2 C3 177.1(10) . . . . ? O2 C1 C2 C3 -3.7(16) . . . . ? Cu1 C1 C2 C3 88(13) . . . . ? C7 C2 C3 C4 -2.0(16) . . . . ? C1 C2 C3 C4 178.2(10) . . . . ? C2 C3 C4 C5 1.1(16) . . . . ? C2 C3 C4 C8 -178.6(9) . . . . ? C3 C4 C5 C6 -0.8(16) . . . . ? C8 C4 C5 C6 178.9(10) . . . . ? C4 C5 C6 C7 1.3(16) . . . . ? C4 C5 C6 N1 -179.8(10) . . . . ? C9 N1 C6 C7 -13.6(17) . . . . ? C9 N1 C6 C5 167.6(10) . . . . ? C3 C2 C7 C6 2.6(16) . . . . ? C1 C2 C7 C6 -177.6(10) . . . . ? C5 C6 C7 C2 -2.2(16) . . . . ? N1 C6 C7 C2 179.0(10) . . . . ? Cu1 O4 C8 O3 4.3(14) 4_556 . . . ? Cu1 O4 C8 C4 -174.8(7) 4_556 . . . ? C5 C4 C8 O3 175.2(10) . . . . ? C3 C4 C8 O3 -5.1(16) . . . . ? C5 C4 C8 O4 -5.8(15) . . . . ? C3 C4 C8 O4 173.9(9) . . . . ? C5 C4 C8 Cu1 -13(2) . . . 4_556 ? C3 C4 C8 Cu1 166.2(12) . . . 4_556 ? C6 N1 C9 O5 3.2(18) . . . . ? C6 N1 C9 C10 -175.1(9) . . . . ? O5 C9 C10 C13 -157.3(11) . . . . ? N1 C9 C10 C13 21.0(16) . . . . ? O5 C9 C10 C11 17.2(16) . . . . ? N1 C9 C10 C11 -164.4(10) . . . . ? C13 C10 C11 C12 0.1(17) . . . . ? C9 C10 C11 C12 -174.8(10) . . . . ? C14 N2 C12 C11 -2.3(17) . . . . ? Cu1 N2 C12 C11 175.6(9) 1_445 . . . ? C10 C11 C12 N2 1.1(18) . . . . ? C11 C10 C13 C14 -0.1(16) . . . . ? C9 C10 C13 C14 174.4(10) . . . . ? C12 N2 C14 C13 2.3(16) . . . . ? Cu1 N2 C14 C13 -175.6(8) 1_445 . . . ? C10 C13 C14 N2 -1.1(17) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.773 _refine_diff_density_min -1.468 _refine_diff_density_rms 0.220 #====END