Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Lu, Jack' 'Babb, Amy M.' _publ_contact_author_name 'Dr Jack Lu' _publ_contact_author_address ; Chemistry University of Houston-Clear Lake 2700 Bay Area Blvd. Houston TX UNITED STATES OF AMERICA ; _publ_contact_author_email 'LU@CL.UH.EDU' _publ_section_title ; An extremely stable open-framework metal-organic polymer with expandable structure and selective absorption capability ; data_spiral_complex_1 _database_code_CSD 163164 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 N2 O4 Cu, 2 H2 O' _chemical_formula_sum 'C12 H12 N2 O6 Cu' _chemical_formula_weight 343.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 4.9579(4) _cell_length_b 25.0785(20) _cell_length_c 10.9881(9) _cell_angle_alpha 90.00 _cell_angle_beta 98.068(1) _cell_angle_gamma 90.00 _cell_volume 1352.70(19) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3196 _cell_measurement_theta_min 1.62 _cell_measurement_theta_max 24.99 _exptl_crystal_description 'Square column' _exptl_crystal_colour 'Dark blue' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.688 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 700 _exptl_absorpt_coefficient_mu 1.644 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.6211 _exptl_absorpt_correction_T_max 0.8960 _exptl_absorpt_process_details ? _diffrn_ambient_temperature 223(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 'Siemens SMART CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 1K _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 3519 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_sigmaI/netI 0.0120 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1976 _reflns_number_gt 1884 _reflns_threshold_expression >4sigma(I) _computing_data_collection 'Siemens SMART software (Siemens, 1996)' _computing_cell_refinement 'Bruker SAINT software (Bruker, 1999)' _computing_data_reduction 'Bruker SAINT software (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0350P)^2^+1.2671P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.011(11) _refine_ls_number_reflns 1937 _refine_ls_number_parameters 196 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0206 _refine_ls_R_factor_gt 0.0200 _refine_ls_wR_factor_ref 0.0529 _refine_ls_wR_factor_gt 0.0524 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.05679(4) 0.113269(9) 0.78373(3) 0.01404(9) Uani 1 1 d . . . O1 O 0.3721(5) 0.32938(10) 1.1785(2) 0.0188(6) Uani 1 1 d . . . O2 O 0.6884(5) 0.34140(8) 1.0551(2) 0.0312(5) Uani 1 1 d . . . O3 O -0.7062(5) -0.06069(8) 0.37844(19) 0.0194(5) Uani 1 1 d . . . O4 O -0.3055(4) -0.10303(7) 0.38772(19) 0.0214(4) Uani 1 1 d . . . O5 O 0.6852(7) 0.38037(14) 0.8142(3) 0.0606(9) Uani 1 1 d G . . H5A H 0.7050 0.3660 0.8950 0.085 Uiso 1 1 d G . . H5B H 0.5085 0.3751 0.7698 0.085 Uiso 1 1 d G . . O6 O 1.1479(8) 0.35694(19) 0.7071(4) 0.0857(12) Uani 1 1 d G . . H6A H 1.0104 0.3596 0.7590 0.120 Uiso 1 1 d G . . H6B H 1.1207 0.3807 0.6391 0.120 Uiso 1 1 d G . . N1 N 0.2072(6) 0.17471(12) 0.8915(3) 0.0184(7) Uani 1 1 d . . . N2 N -0.1013(5) 0.05545(11) 0.6661(2) 0.0179(6) Uani 1 1 d . . . C1 C 0.1048(7) 0.18984(13) 0.9929(3) 0.0221(7) Uani 1 1 d . . . H1 H -0.0299 0.1685 1.0207 0.027 Uiso 1 1 calc R . . C2 C 0.1880(8) 0.23519(13) 1.0579(3) 0.0229(8) Uani 1 1 d . . . H2 H 0.1112 0.2444 1.1285 0.027 Uiso 1 1 calc R . . C3 C 0.3872(7) 0.26724(13) 1.0178(3) 0.0185(7) Uani 1 1 d . . . C4 C 0.4957(6) 0.25163(10) 0.9131(3) 0.0204(6) Uani 1 1 d . . . H4 H 0.6309 0.2723 0.8837 0.024 Uiso 1 1 calc R . . C5 C 0.4023(6) 0.20531(10) 0.8528(2) 0.0204(6) Uani 1 1 d . . . H5 H 0.4773 0.1948 0.7825 0.024 Uiso 1 1 calc R . . C6 C 0.4919(7) 0.31715(12) 1.0879(3) 0.0181(7) Uani 1 1 d . . . C7 C -0.3332(6) 0.06441(10) 0.5902(3) 0.0231(6) Uani 1 1 d . . . H7 H -0.4174 0.0979 0.5926 0.028 Uiso 1 1 calc R . . C8 C -0.4539(6) 0.02653(11) 0.5085(3) 0.0240(6) Uani 1 1 d . . . H8 H -0.6185 0.0342 0.4579 0.029 Uiso 1 1 calc R . . C9 C -0.3295(6) -0.02297(10) 0.5019(3) 0.0176(5) Uani 1 1 d . . . C10 C -0.0883(6) -0.03222(10) 0.5804(3) 0.0215(6) Uani 1 1 d . . . H10 H 0.0031 -0.0650 0.5781 0.026 Uiso 1 1 calc R . . C11 C 0.0154(6) 0.00720(10) 0.6615(3) 0.0222(6) Uani 1 1 d . . . H11 H 0.1748 0.0000 0.7161 0.027 Uiso 1 1 calc R . . C12 C -0.4522(6) -0.06609(9) 0.4156(2) 0.0160(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 Cu 0.01696(15) 0.00928(13) 0.01406(14) -0.00016(16) -0.00417(9) -0.00011(17) O1 0.0242(13) 0.0133(11) 0.0174(13) -0.0042(9) -0.0028(10) -0.0011(9) O2 0.0333(13) 0.0272(10) 0.0339(12) -0.0110(9) 0.0072(10) -0.0135(10) O3 0.0199(12) 0.0121(9) 0.0233(11) -0.0009(8) -0.0064(9) 0.0011(8) O4 0.0190(10) 0.0166(9) 0.0279(11) -0.0068(8) 0.0010(9) 0.0020(8) O5 0.061(2) 0.0678(19) 0.0514(19) 0.0163(15) 0.0006(15) -0.0200(16) O6 0.061(2) 0.120(3) 0.075(3) -0.008(2) 0.0055(19) -0.029(2) N1 0.0213(15) 0.0130(14) 0.0193(15) 0.0005(12) -0.0033(12) 0.0008(11) N2 0.0172(14) 0.0156(13) 0.0193(13) -0.0020(10) -0.0030(11) 0.0008(10) C1 0.0235(17) 0.0206(15) 0.0228(17) -0.0022(13) 0.0056(14) -0.0023(13) C2 0.0257(18) 0.0201(16) 0.0229(18) -0.0053(14) 0.0033(15) -0.0028(14) C3 0.0190(17) 0.0159(15) 0.0192(16) -0.0019(13) -0.0022(13) 0.0001(12) C4 0.0233(15) 0.0153(12) 0.0222(14) 0.0002(11) 0.0017(11) -0.0037(10) C5 0.0249(15) 0.0186(13) 0.0175(14) -0.0016(10) 0.0027(11) -0.0001(11) C6 0.0215(17) 0.0103(13) 0.0196(17) -0.0028(11) -0.0075(14) 0.0003(12) C7 0.0231(15) 0.0127(12) 0.0309(16) -0.0016(12) -0.0050(13) 0.0042(11) C8 0.0203(15) 0.0180(14) 0.0296(16) -0.0037(12) -0.0109(13) 0.0031(11) C9 0.0190(14) 0.0156(12) 0.0176(13) -0.0002(11) 0.0005(11) -0.0004(10) C10 0.0236(15) 0.0140(12) 0.0241(14) -0.0051(11) -0.0058(11) 0.0057(11) C11 0.0206(14) 0.0181(13) 0.0247(15) -0.0028(11) -0.0082(12) 0.0038(11) C12 0.0180(14) 0.0136(12) 0.0146(13) 0.0031(10) -0.0039(11) -0.0010(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu O3 1.965(2) 2_655 ? Cu O1 1.987(2) 4_454 ? Cu N1 2.021(3) . ? Cu N2 2.026(3) . ? Cu O4 2.275(2) 2 ? O1 C6 1.266(5) . ? O1 Cu 1.987(2) 4 ? O2 C6 1.244(4) . ? O3 C12 1.276(3) . ? O3 Cu 1.965(2) 2_454 ? O4 C12 1.242(3) . ? O4 Cu 2.275(2) 2_554 ? N1 C1 1.342(5) . ? N1 C5 1.350(4) . ? N2 C7 1.341(4) . ? N2 C11 1.345(4) . ? C1 C2 1.375(5) . ? C2 C3 1.392(4) . ? C3 C4 1.393(5) . ? C3 C6 1.522(4) . ? C4 C5 1.384(4) . ? C7 C8 1.384(4) . ? C8 C9 1.393(4) . ? C9 C10 1.392(4) . ? C9 C12 1.509(3) . ? C10 C11 1.382(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 O3 Cu O1 170.68(11) 2_655 4_454 ? O3 Cu N1 93.28(10) 2_655 . ? O1 Cu N1 83.75(7) 4_454 . ? O3 Cu N2 90.38(8) 2_655 . ? O1 Cu N2 92.38(11) 4_454 . ? N1 Cu N2 175.98(12) . . ? O3 Cu O4 96.54(9) 2_655 2 ? O1 Cu O4 92.42(9) 4_454 2 ? N1 Cu O4 92.53(11) . 2 ? N2 Cu O4 88.71(9) . 2 ? C6 O1 Cu 113.8(2) . 4 ? C12 O3 Cu 126.05(18) . 2_454 ? C12 O4 Cu 137.62(19) . 2_554 ? C1 N1 C5 118.2(3) . . ? C1 N1 Cu 123.4(3) . . ? C5 N1 Cu 118.1(2) . . ? C7 N2 C11 117.6(3) . . ? C7 N2 Cu 119.9(2) . . ? C11 N2 Cu 122.53(19) . . ? N1 C1 C2 122.9(4) . . ? C1 C2 C3 119.2(3) . . ? C2 C3 C4 118.2(2) . . ? C2 C3 C6 121.4(3) . . ? C4 C3 C6 120.4(3) . . ? C5 C4 C3 119.3(3) . . ? N1 C5 C4 122.2(3) . . ? O2 C6 O1 125.6(3) . . ? O2 C6 C3 118.7(3) . . ? O1 C6 C3 115.6(3) . . ? N2 C7 C8 122.9(3) . . ? C7 C8 C9 119.4(2) . . ? C10 C9 C8 117.7(2) . . ? C10 C9 C12 120.4(2) . . ? C8 C9 C12 122.0(2) . . ? C11 C10 C9 119.4(2) . . ? N2 C11 C10 123.0(2) . . ? O4 C12 O3 125.9(2) . . ? O4 C12 C9 119.4(2) . . ? O3 C12 C9 114.7(2) . . ? 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 O3 Cu N1 C1 -89.1(3) 2_655 . . . ? O1 Cu N1 C1 99.8(3) 4_454 . . . ? N2 Cu N1 C1 115.5(18) . . . . ? O4 Cu N1 C1 7.6(3) 2 . . . ? O3 Cu N1 C5 97.8(2) 2_655 . . . ? O1 Cu N1 C5 -73.3(2) 4_454 . . . ? N2 Cu N1 C5 -58(2) . . . . ? O4 Cu N1 C5 -165.5(2) 2 . . . ? O3 Cu N2 C7 164.5(3) 2_655 . . . ? O1 Cu N2 C7 -24.4(3) 4_454 . . . ? N1 Cu N2 C7 -40(2) . . . . ? O4 Cu N2 C7 67.9(3) 2 . . . ? O3 Cu N2 C11 -14.6(3) 2_655 . . . ? O1 Cu N2 C11 156.5(3) 4_454 . . . ? N1 Cu N2 C11 140.9(18) . . . . ? O4 Cu N2 C11 -111.1(3) 2 . . . ? C5 N1 C1 C2 0.6(5) . . . . ? Cu N1 C1 C2 -172.5(3) . . . . ? N1 C1 C2 C3 0.0(5) . . . . ? C1 C2 C3 C4 -0.4(4) . . . . ? C1 C2 C3 C6 -178.5(4) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? C6 C3 C4 C5 178.3(3) . . . . ? C1 N1 C5 C4 -0.9(4) . . . . ? Cu N1 C5 C4 172.6(2) . . . . ? C3 C4 C5 N1 0.5(4) . . . . ? Cu O1 C6 O2 -8.1(4) 4 . . . ? Cu O1 C6 C3 169.8(2) 4 . . . ? C2 C3 C6 O2 173.0(3) . . . . ? C4 C3 C6 O2 -5.1(4) . . . . ? C2 C3 C6 O1 -5.0(4) . . . . ? C4 C3 C6 O1 176.9(3) . . . . ? C11 N2 C7 C8 -0.2(5) . . . . ? Cu N2 C7 C8 -179.3(3) . . . . ? N2 C7 C8 C9 -1.2(5) . . . . ? C7 C8 C9 C10 1.0(5) . . . . ? C7 C8 C9 C12 179.4(3) . . . . ? C8 C9 C10 C11 0.7(5) . . . . ? C12 C9 C10 C11 -177.8(3) . . . . ? C7 N2 C11 C10 2.0(5) . . . . ? Cu N2 C11 C10 -178.9(2) . . . . ? C9 C10 C11 N2 -2.3(5) . . . . ? Cu O4 C12 O3 115.2(3) 2_554 . . . ? Cu O4 C12 C9 -65.5(4) 2_554 . . . ? Cu O3 C12 O4 7.8(4) 2_454 . . . ? Cu O3 C12 C9 -171.51(18) 2_454 . . . ? C10 C9 C12 O4 -21.1(4) . . . . ? C8 C9 C12 O4 160.5(3) . . . . ? C10 C9 C12 O3 158.3(3) . . . . ? C8 C9 C12 O3 -20.1(4) . . . . ? 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 O5 H5A O2 0.95 1.88 2.820(4) 171.1 . O5 H5B O6 0.95 1.88 2.819(5) 169.3 1_455 O6 H6A O5 0.95 1.87 2.784(6) 159.3 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.192 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.046 data_Spiral_complex_2 _database_code_CSD 163165 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_sum 'C12 H8 N2 O4 Cu' _chemical_formula_weight 307.74 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 4.9577(3) _cell_length_b 24.6312(15) _cell_length_c 11.2322(7) _cell_angle_alpha 90.00 _cell_angle_beta 98.325(1) _cell_angle_gamma 90.00 _cell_volume 1357.16(14) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3207 _cell_measurement_theta_min 1.65 _cell_measurement_theta_max 24.99 _exptl_crystal_description 'Prismatic block' _exptl_crystal_colour Blue _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 620 _exptl_absorpt_coefficient_mu 1.619 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.6926 _exptl_absorpt_correction_T_max 0.8913 _exptl_absorpt_process_details ? _diffrn_ambient_temperature 223(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 'Siemens SMART CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 1K _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 3539 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0133 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2166 _reflns_number_gt 2047 _reflns_threshold_expression >4sigma(I) _computing_data_collection 'Siemens SMART software (Siemens, 1996)' _computing_cell_refinement 'Bruker SAINT software (Bruker, 1999)' _computing_data_reduction 'Bruker SAINT software (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0385P)^2^+0.9749P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.017(11) _refine_ls_number_reflns 2124 _refine_ls_number_parameters 172 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0212 _refine_ls_R_factor_gt 0.0203 _refine_ls_wR_factor_ref 0.0563 _refine_ls_wR_factor_gt 0.0555 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.05728(4) 0.113878(9) 0.78317(3) 0.01521(9) Uani 1 1 d . . . O1 O 0.3743(5) 0.32857(10) 1.1807(2) 0.0213(6) Uani 1 1 d . . . O2 O 0.6965(4) 0.34155(9) 1.0652(2) 0.0421(6) Uani 1 1 d . . . O3 O -0.7123(4) -0.05965(9) 0.37703(19) 0.0202(5) Uani 1 1 d . . . O4 O -0.3094(4) -0.10206(8) 0.38651(19) 0.0224(4) Uani 1 1 d . . . N1 N 0.2114(5) 0.17552(13) 0.8900(3) 0.0196(7) Uani 1 1 d . . . N2 N -0.1086(5) 0.05518(11) 0.6691(2) 0.0182(6) Uani 1 1 d . . . C1 C 0.1099(7) 0.18927(13) 0.9899(3) 0.0254(8) Uani 1 1 d . . . H1 H -0.0244 0.1670 1.0157 0.030 Uiso 1 1 calc R . . C2 C 0.1945(7) 0.23487(13) 1.0565(3) 0.0252(8) Uani 1 1 d . . . H2 H 0.1187 0.2433 1.1262 0.030 Uiso 1 1 calc R . . C3 C 0.3918(6) 0.26801(13) 1.0196(3) 0.0209(7) Uani 1 1 d . . . C4 C 0.4981(5) 0.25373(10) 0.9167(3) 0.0238(6) Uani 1 1 d . . . H4 H 0.6331 0.2753 0.8895 0.029 Uiso 1 1 calc R . . C5 C 0.4045(5) 0.20757(10) 0.8544(2) 0.0219(6) Uani 1 1 d . . . H5 H 0.4782 0.1982 0.7847 0.026 Uiso 1 1 calc R . . C6 C 0.4988(6) 0.31722(13) 1.0927(3) 0.0215(7) Uani 1 1 d . . . C7 C -0.3425(6) 0.06484(10) 0.5958(3) 0.0238(6) Uani 1 1 d . . . H7 H -0.4275 0.0987 0.6002 0.029 Uiso 1 1 calc R . . C8 C -0.4627(6) 0.02727(11) 0.5146(3) 0.0240(6) Uani 1 1 d . . . H8 H -0.6288 0.0354 0.4663 0.029 Uiso 1 1 calc R . . C9 C -0.3390(5) -0.02260(11) 0.5041(3) 0.0184(6) Uani 1 1 d . . . C10 C -0.0975(6) -0.03268(10) 0.5795(3) 0.0241(6) Uani 1 1 d . . . H10 H -0.0068 -0.0660 0.5757 0.029 Uiso 1 1 calc R . . C11 C 0.0086(5) 0.00675(10) 0.6605(3) 0.0231(6) Uani 1 1 d . . . H11 H 0.1711 -0.0008 0.7120 0.028 Uiso 1 1 calc R . . C12 C -0.4589(5) -0.06530(10) 0.4151(2) 0.0171(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 Cu 0.01833(14) 0.00982(13) 0.01496(15) -0.00003(16) -0.00609(9) -0.00029(16) O1 0.0276(13) 0.0154(12) 0.0187(13) -0.0032(9) -0.0047(10) -0.0018(8) O2 0.0373(12) 0.0353(12) 0.0556(16) -0.0221(11) 0.0131(11) -0.0194(10) O3 0.0206(10) 0.0124(10) 0.0240(12) -0.0017(8) -0.0083(9) 0.0028(8) O4 0.0216(9) 0.0177(9) 0.0267(12) -0.0052(7) -0.0011(8) 0.0012(8) N1 0.0205(14) 0.0150(14) 0.0214(16) 0.0000(12) -0.0033(12) -0.0006(11) N2 0.0174(12) 0.0157(13) 0.0196(14) -0.0019(9) -0.0044(10) -0.0012(10) C1 0.0288(17) 0.0233(17) 0.0245(18) -0.0041(12) 0.0054(14) -0.0032(13) C2 0.0280(17) 0.0222(17) 0.0252(19) -0.0065(14) 0.0039(14) -0.0062(13) C3 0.0219(16) 0.0162(15) 0.0226(18) -0.0034(13) -0.0041(13) 0.0011(11) C4 0.0245(14) 0.0195(13) 0.0269(16) -0.0025(11) 0.0024(11) -0.0043(10) C5 0.0246(13) 0.0201(13) 0.0204(15) -0.0020(10) 0.0015(11) -0.0013(11) C6 0.0207(15) 0.0153(14) 0.0251(19) -0.0043(12) -0.0083(13) -0.0025(12) C7 0.0228(13) 0.0138(13) 0.0316(17) -0.0049(12) -0.0065(12) 0.0064(10) C8 0.0180(13) 0.0223(14) 0.0276(17) -0.0020(12) -0.0110(11) 0.0025(11) C9 0.0176(13) 0.0166(13) 0.0194(15) -0.0017(11) -0.0020(11) -0.0011(10) C10 0.0223(13) 0.0168(13) 0.0296(16) -0.0039(11) -0.0083(11) 0.0056(10) C11 0.0221(13) 0.0182(13) 0.0250(15) -0.0043(10) -0.0103(11) 0.0058(10) C12 0.0209(13) 0.0153(13) 0.0135(13) 0.0012(10) -0.0033(11) -0.0019(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu O3 1.963(2) 2_655 ? Cu O1 1.964(2) 4_454 ? Cu N1 2.016(3) . ? Cu N2 2.026(3) . ? Cu O4 2.313(2) 2 ? O1 C6 1.269(4) . ? O1 Cu 1.964(2) 4 ? O2 C6 1.226(4) . ? O3 C12 1.275(3) . ? O3 Cu 1.963(2) 2_454 ? O4 C12 1.242(3) . ? O4 Cu 2.313(2) 2_554 ? N1 C1 1.338(5) . ? N1 C5 1.345(4) . ? N2 C11 1.337(4) . ? N2 C7 1.343(4) . ? C1 C2 1.381(5) . ? C2 C3 1.382(4) . ? C3 C4 1.383(4) . ? C3 C6 1.516(4) . ? C4 C5 1.380(4) . ? C7 C8 1.373(4) . ? C8 C9 1.386(3) . ? C9 C10 1.386(4) . ? C9 C12 1.512(4) . ? C10 C11 1.382(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 O3 Cu O1 171.84(10) 2_655 4_454 ? O3 Cu N1 92.97(11) 2_655 . ? O1 Cu N1 84.75(7) 4_454 . ? O3 Cu N2 90.32(7) 2_655 . ? O1 Cu N2 91.92(12) 4_454 . ? N1 Cu N2 176.67(12) . . ? O3 Cu O4 94.79(8) 2_655 2 ? O1 Cu O4 93.16(8) 4_454 2 ? N1 Cu O4 93.08(10) . 2 ? N2 Cu O4 87.19(9) . 2 ? C6 O1 Cu 112.3(2) . 4 ? C12 O3 Cu 125.08(18) . 2_454 ? C12 O4 Cu 139.80(18) . 2_554 ? C1 N1 C5 118.1(3) . . ? C1 N1 Cu 122.2(2) . . ? C5 N1 Cu 119.3(2) . . ? C11 N2 C7 117.4(3) . . ? C11 N2 Cu 122.79(19) . . ? C7 N2 Cu 119.8(2) . . ? N1 C1 C2 122.6(3) . . ? C1 C2 C3 119.4(3) . . ? C2 C3 C4 118.1(2) . . ? C2 C3 C6 121.2(3) . . ? C4 C3 C6 120.6(3) . . ? C5 C4 C3 119.5(3) . . ? N1 C5 C4 122.3(3) . . ? O2 C6 O1 125.8(3) . . ? O2 C6 C3 119.0(3) . . ? O1 C6 C3 115.2(3) . . ? N2 C7 C8 122.8(2) . . ? C7 C8 C9 120.0(2) . . ? C8 C9 C10 117.4(2) . . ? C8 C9 C12 122.5(2) . . ? C10 C9 C12 120.1(2) . . ? C11 C10 C9 119.3(2) . . ? N2 C11 C10 123.1(2) . . ? O4 C12 O3 126.1(2) . . ? O4 C12 C9 119.1(2) . . ? O3 C12 C9 114.8(2) . . ? 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 O3 Cu N1 C1 -86.9(3) 2_655 . . . ? O1 Cu N1 C1 100.9(3) 4_454 . . . ? N2 Cu N1 C1 103(2) . . . . ? O4 Cu N1 C1 8.0(3) 2 . . . ? O3 Cu N1 C5 99.9(2) 2_655 . . . ? O1 Cu N1 C5 -72.3(2) 4_454 . . . ? N2 Cu N1 C5 -71(2) . . . . ? O4 Cu N1 C5 -165.1(2) 2 . . . ? O3 Cu N2 C11 -18.5(2) 2_655 . . . ? O1 Cu N2 C11 153.6(2) 4_454 . . . ? N1 Cu N2 C11 152(2) . . . . ? O4 Cu N2 C11 -113.3(2) 2 . . . ? O3 Cu N2 C7 163.3(3) 2_655 . . . ? O1 Cu N2 C7 -24.5(3) 4_454 . . . ? N1 Cu N2 C7 -26(2) . . . . ? O4 Cu N2 C7 68.5(2) 2 . . . ? C5 N1 C1 C2 0.4(5) . . . . ? Cu N1 C1 C2 -172.9(3) . . . . ? N1 C1 C2 C3 0.0(5) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? C1 C2 C3 C6 -177.5(4) . . . . ? C2 C3 C4 C5 0.3(4) . . . . ? C6 C3 C4 C5 177.5(3) . . . . ? C1 N1 C5 C4 -0.4(4) . . . . ? Cu N1 C5 C4 173.1(2) . . . . ? C3 C4 C5 N1 0.1(4) . . . . ? Cu O1 C6 O2 -6.3(4) 4 . . . ? Cu O1 C6 C3 171.9(2) 4 . . . ? C2 C3 C6 O2 171.0(3) . . . . ? C4 C3 C6 O2 -6.1(4) . . . . ? C2 C3 C6 O1 -7.3(4) . . . . ? C4 C3 C6 O1 175.5(3) . . . . ? C11 N2 C7 C8 0.3(5) . . . . ? Cu N2 C7 C8 178.6(2) . . . . ? N2 C7 C8 C9 -1.5(5) . . . . ? C7 C8 C9 C10 1.4(5) . . . . ? C7 C8 C9 C12 -179.0(2) . . . . ? C8 C9 C10 C11 -0.2(5) . . . . ? C12 C9 C10 C11 -179.8(3) . . . . ? C7 N2 C11 C10 0.9(5) . . . . ? Cu N2 C11 C10 -177.3(2) . . . . ? C9 C10 C11 N2 -1.0(5) . . . . ? Cu O4 C12 O3 113.0(3) 2_554 . . . ? Cu O4 C12 C9 -67.6(4) 2_554 . . . ? Cu O3 C12 O4 10.2(4) 2_454 . . . ? Cu O3 C12 C9 -169.26(18) 2_454 . . . ? C8 C9 C12 O4 160.7(3) . . . . ? C10 C9 C12 O4 -19.7(4) . . . . ? C8 C9 C12 O3 -19.8(4) . . . . ? C10 C9 C12 O3 159.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.341 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.048 data_Spiral_complex_3 _database_code_CSD 163166 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 N2 O4 Cu, C H4 O' _chemical_formula_sum 'C13 H12 N2 O5 Cu' _chemical_formula_weight 339.79 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 4.9213(3) _cell_length_b 25.1423(16) _cell_length_c 10.8011(7) _cell_angle_alpha 90.00 _cell_angle_beta 96.920(1) _cell_angle_gamma 90.00 _cell_volume 1326.71(15) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2953 _cell_measurement_theta_min 1.62 _cell_measurement_theta_max 25.00 _exptl_crystal_description 'Thick plate' _exptl_crystal_colour Blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.701 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 1.670 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.7361 _exptl_absorpt_correction_T_max 0.9332 _exptl_absorpt_process_details ? _diffrn_ambient_temperature 223(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 'Siemens SMART CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 1K _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 3468 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0136 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1570 _reflns_number_gt 1471 _reflns_threshold_expression >4sigma(I) _computing_data_collection 'Siemens SMART software (Siemens, 1996)' _computing_cell_refinement 'Bruker SAINT software (Bruker, 1999)' _computing_data_reduction 'Bruker SAINT software (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0343P)^2^+1.2455P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0001(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.011(12) _refine_ls_number_reflns 1540 _refine_ls_number_parameters 191 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0207 _refine_ls_R_factor_gt 0.0193 _refine_ls_wR_factor_ref 0.0513 _refine_ls_wR_factor_gt 0.0501 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.242 _refine_ls_shift/su_mean 0.009 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.05710(5) 0.113292(10) 0.78433(4) 0.01315(11) Uani 1 1 d . . . O1 O 0.3834(5) 0.33103(11) 1.1718(3) 0.0174(6) Uani 1 1 d . . . O2 O 0.6818(5) 0.34493(9) 1.0355(3) 0.0334(6) Uani 1 1 d . . . O3 O -0.7070(5) -0.06175(9) 0.3822(2) 0.0178(6) Uani 1 1 d . . . O4 O -0.3073(4) -0.10482(8) 0.3939(2) 0.0192(5) Uani 1 1 d . . . N1 N 0.2078(6) 0.17570(13) 0.8879(3) 0.0168(7) Uani 1 1 d . . . N2 N -0.1040(5) 0.05429(12) 0.6719(3) 0.0161(7) Uani 1 1 d . . . C1 C 0.1129(8) 0.19115(14) 0.9936(4) 0.0212(9) Uani 1 1 d . . . H1 H -0.0172 0.1697 1.0266 0.025 Uiso 1 1 calc R . . C2 C 0.1978(8) 0.23707(14) 1.0557(4) 0.0213(9) Uani 1 1 d . . . H2 H 0.1259 0.2467 1.1293 0.026 Uiso 1 1 calc R . . C3 C 0.3911(7) 0.26911(15) 1.0086(4) 0.0172(8) Uani 1 1 d . . . C4 C 0.4951(6) 0.25251(12) 0.9003(3) 0.0205(7) Uani 1 1 d . . . H4 H 0.6284 0.2728 0.8664 0.025 Uiso 1 1 calc R . . C5 C 0.3996(6) 0.20596(12) 0.8441(3) 0.0203(7) Uani 1 1 d . . . H5 H 0.4719 0.1948 0.7717 0.024 Uiso 1 1 calc R . . C6 C 0.4972(7) 0.31984(14) 1.0760(4) 0.0175(8) Uani 1 1 d . . . C7 C -0.3362(7) 0.06313(12) 0.5943(4) 0.0206(7) Uani 1 1 d . . . H7 H -0.4195 0.0968 0.5948 0.025 Uiso 1 1 calc R . . C8 C -0.4553(7) 0.02471(12) 0.5144(4) 0.0213(7) Uani 1 1 d . . . H8 H -0.6184 0.0322 0.4627 0.026 Uiso 1 1 calc R . . C9 C -0.3347(6) -0.02512(12) 0.5101(3) 0.0154(6) Uani 1 1 d . . . C10 C -0.0986(6) -0.03456(12) 0.5911(3) 0.0195(7) Uani 1 1 d . . . H10 H -0.0109 -0.0678 0.5918 0.023 Uiso 1 1 calc R . . C11 C 0.0063(6) 0.00543(11) 0.6708(3) 0.0188(7) Uani 1 1 d . . . H11 H 0.1628 -0.0019 0.7271 0.023 Uiso 1 1 calc R . . C12 C -0.4547(6) -0.06785(11) 0.4213(3) 0.0153(6) Uani 1 1 d . . . O5 O 0.7359(14) 0.3686(3) 0.7766(9) 0.049(2) Uiso 0.50 1 d PD A 1 H5A H 0.7085 0.3657 0.8619 0.058 Uiso 0.50 1 calc PR A 1 C13 C 1.0271(17) 0.3738(5) 0.7668(16) 0.047(4) Uiso 0.50 1 d PD A 1 H13A H 1.1062 0.4001 0.8261 0.070 Uiso 0.50 1 calc PR A 1 H13B H 1.0527 0.3848 0.6829 0.070 Uiso 0.50 1 calc PR A 1 H13C H 1.1165 0.3398 0.7848 0.070 Uiso 0.50 1 calc PR A 1 O5' O 0.7500(13) 0.3817(3) 0.7961(8) 0.0370(19) Uiso 0.50 1 d PD B 2 H5B H 0.7355 0.3765 0.8822 0.044 Uiso 0.50 1 calc PR B 2 C13' C 1.0143(18) 0.3615(5) 0.7674(15) 0.048(4) Uiso 0.50 1 d PD B 2 H13D H 1.1609 0.3813 0.8146 0.072 Uiso 0.50 1 calc PR B 2 H13E H 1.0263 0.3656 0.6789 0.072 Uiso 0.50 1 calc PR B 2 H13F H 1.0308 0.3242 0.7896 0.072 Uiso 0.50 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.01583(17) 0.00952(16) 0.01300(17) 0.0002(2) -0.00277(11) -0.00011(17) O1 0.0217(14) 0.0122(12) 0.0172(15) -0.0023(11) -0.0022(12) -0.0019(9) O2 0.0367(14) 0.0281(12) 0.0374(15) -0.0125(12) 0.0125(12) -0.0170(11) O3 0.0167(11) 0.0130(11) 0.0215(14) -0.0014(11) -0.0065(11) 0.0021(9) O4 0.0181(10) 0.0165(10) 0.0230(13) -0.0056(10) 0.0029(10) 0.0016(8) N1 0.0195(16) 0.0153(16) 0.0144(17) 0.0014(13) -0.0024(14) 0.0011(12) N2 0.0177(14) 0.0140(14) 0.0162(16) -0.0015(12) 0.0002(12) -0.0008(10) C1 0.0256(18) 0.0175(18) 0.021(2) 0.0012(15) 0.0055(16) -0.0056(13) C2 0.026(2) 0.0205(19) 0.017(2) -0.0061(17) 0.0042(17) -0.0034(14) C3 0.0180(18) 0.0152(16) 0.018(2) 0.0009(15) -0.0001(16) 0.0006(13) C4 0.0225(17) 0.0185(15) 0.0215(18) -0.0019(14) 0.0058(14) -0.0053(12) C5 0.0245(16) 0.0210(15) 0.0154(16) -0.0023(14) 0.0029(13) -0.0023(13) C6 0.0199(16) 0.0129(16) 0.018(2) -0.0033(15) -0.0032(15) 0.0005(13) C7 0.0219(16) 0.0113(14) 0.0263(19) 0.0022(15) -0.0058(15) 0.0026(12) C8 0.0167(16) 0.0207(16) 0.0240(19) -0.0035(15) -0.0082(14) 0.0022(12) C9 0.0151(14) 0.0157(15) 0.0154(17) -0.0001(13) 0.0019(13) -0.0016(11) C10 0.0190(15) 0.0147(14) 0.0238(18) -0.0030(13) -0.0022(13) 0.0030(12) C11 0.0164(14) 0.0162(14) 0.0219(18) -0.0014(14) -0.0057(13) 0.0035(11) C12 0.0202(16) 0.0144(14) 0.0109(15) 0.0020(13) 0.0008(13) -0.0034(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu O3 1.962(2) 2_655 ? Cu O1 1.979(3) 4_454 ? Cu N1 2.016(3) . ? Cu N2 2.018(3) . ? Cu O4 2.275(2) 2 ? O1 C6 1.266(5) . ? O1 Cu 1.979(3) 4 ? O2 C6 1.229(4) . ? O3 C12 1.272(4) . ? O3 Cu 1.962(2) 2_454 ? O4 C12 1.236(4) . ? O4 Cu 2.275(2) 2_554 ? N1 C1 1.343(5) . ? N1 C5 1.342(5) . ? N2 C11 1.344(4) . ? N2 C7 1.352(4) . ? C1 C2 1.375(5) . ? C2 C3 1.389(4) . ? C3 C4 1.396(5) . ? C3 C6 1.529(5) . ? C4 C5 1.375(4) . ? C7 C8 1.379(5) . ? C8 C9 1.390(4) . ? C9 C10 1.388(4) . ? C9 C12 1.512(4) . ? C10 C11 1.382(4) . ? O5 C13 1.456(5) . ? O5' C13' 1.464(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Cu O1 169.08(10) 2_655 4_454 ? O3 Cu N1 93.49(12) 2_655 . ? O1 Cu N1 83.87(10) 4_454 . ? O3 Cu N2 90.16(9) 2_655 . ? O1 Cu N2 92.35(13) 4_454 . ? N1 Cu N2 176.19(14) . . ? O3 Cu O4 96.32(9) 2_655 2 ? O1 Cu O4 94.39(9) 4_454 2 ? N1 Cu O4 92.57(11) . 2 ? N2 Cu O4 88.11(10) . 2 ? C6 O1 Cu 117.3(2) . 4 ? C12 O3 Cu 126.1(2) . 2_454 ? C12 O4 Cu 135.8(2) . 2_554 ? C1 N1 C5 117.8(3) . . ? C1 N1 Cu 123.7(3) . . ? C5 N1 Cu 118.3(3) . . ? C11 N2 C7 117.2(3) . . ? C11 N2 Cu 123.2(2) . . ? C7 N2 Cu 119.6(2) . . ? N1 C1 C2 122.8(4) . . ? C1 C2 C3 119.3(3) . . ? C2 C3 C4 118.0(3) . . ? C2 C3 C6 121.3(3) . . ? C4 C3 C6 120.6(3) . . ? C5 C4 C3 118.9(3) . . ? N1 C5 C4 123.0(3) . . ? O2 C6 O1 126.5(3) . . ? O2 C6 C3 119.0(3) . . ? O1 C6 C3 114.5(3) . . ? N2 C7 C8 122.5(3) . . ? C7 C8 C9 120.1(3) . . ? C10 C9 C8 117.5(3) . . ? C10 C9 C12 120.8(3) . . ? C8 C9 C12 121.7(3) . . ? C11 C10 C9 119.3(3) . . ? N2 C11 C10 123.3(3) . . ? O4 C12 O3 126.1(3) . . ? O4 C12 C9 119.4(3) . . ? O3 C12 C9 114.6(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Cu N1 C1 -86.0(3) 2_655 . . . ? O1 Cu N1 C1 104.6(3) 4_454 . . . ? N2 Cu N1 C1 111(2) . . . . ? O4 Cu N1 C1 10.4(3) 2 . . . ? O3 Cu N1 C5 99.2(3) 2_655 . . . ? O1 Cu N1 C5 -70.2(3) 4_454 . . . ? N2 Cu N1 C5 -64(2) . . . . ? O4 Cu N1 C5 -164.3(3) 2 . . . ? O3 Cu N2 C11 -13.4(3) 2_655 . . . ? O1 Cu N2 C11 156.0(3) 4_454 . . . ? N1 Cu N2 C11 150.0(19) . . . . ? O4 Cu N2 C11 -109.7(3) 2 . . . ? O3 Cu N2 C7 165.7(3) 2_655 . . . ? O1 Cu N2 C7 -24.9(3) 4_454 . . . ? N1 Cu N2 C7 -31(2) . . . . ? O4 Cu N2 C7 69.4(3) 2 . . . ? C5 N1 C1 C2 2.0(6) . . . . ? Cu N1 C1 C2 -172.8(3) . . . . ? N1 C1 C2 C3 -0.4(6) . . . . ? C1 C2 C3 C4 -1.2(5) . . . . ? C1 C2 C3 C6 -178.5(4) . . . . ? C2 C3 C4 C5 1.0(5) . . . . ? C6 C3 C4 C5 178.4(3) . . . . ? C1 N1 C5 C4 -2.2(5) . . . . ? Cu N1 C5 C4 172.9(3) . . . . ? C3 C4 C5 N1 0.7(5) . . . . ? Cu O1 C6 O2 -11.2(5) 4 . . . ? Cu O1 C6 C3 167.5(2) 4 . . . ? C2 C3 C6 O2 175.0(3) . . . . ? C4 C3 C6 O2 -2.3(5) . . . . ? C2 C3 C6 O1 -3.8(5) . . . . ? C4 C3 C6 O1 178.9(3) . . . . ? C11 N2 C7 C8 -1.5(5) . . . . ? Cu N2 C7 C8 179.4(3) . . . . ? N2 C7 C8 C9 -1.0(6) . . . . ? C7 C8 C9 C10 1.9(6) . . . . ? C7 C8 C9 C12 -178.3(3) . . . . ? C8 C9 C10 C11 -0.4(5) . . . . ? C12 C9 C10 C11 179.8(3) . . . . ? C7 N2 C11 C10 3.1(5) . . . . ? Cu N2 C11 C10 -177.9(3) . . . . ? C9 C10 C11 N2 -2.1(5) . . . . ? Cu O4 C12 O3 112.6(3) 2_554 . . . ? Cu O4 C12 C9 -68.0(4) 2_554 . . . ? Cu O3 C12 O4 7.9(5) 2_454 . . . ? Cu O3 C12 C9 -171.5(2) 2_454 . . . ? C10 C9 C12 O4 -21.0(5) . . . . ? C8 C9 C12 O4 159.2(4) . . . . ? C10 C9 C12 O3 158.4(3) . . . . ? C8 C9 C12 O3 -21.3(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 O5 H5A O2 0.95 1.97 2.903(10) 168.2 . O5' H5B O2 0.95 1.88 2.804(8) 162.4 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.344 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.051 data_Spiral_complex_4 _database_code_CSD 163167 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 N2 O4 Cu, C2 H6 O' _chemical_formula_sum 'C14 H14 N2 O5 Cu' _chemical_formula_weight 353.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 5.1186(3) _cell_length_b 24.6268(13) _cell_length_c 11.3254(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.021(1) _cell_angle_gamma 90.00 _cell_volume 1405.84(13) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3234 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 25.00 _exptl_crystal_description 'Prismatic block' _exptl_crystal_colour Blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 1.580 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.7221 _exptl_absorpt_correction_T_max 0.9491 _exptl_absorpt_process_details ? _diffrn_ambient_temperature 223(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 'Siemens SMART CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 1K _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 3672 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0132 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1988 _reflns_number_gt 1868 _reflns_threshold_expression >4sigma(I) _computing_data_collection 'Siemens SMART software (Siemens, 1996)' _computing_cell_refinement 'Bruker SAINT software (Bruker, 1999)' _computing_data_reduction 'Bruker SAINT software (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0359P)^2^+1.1416P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.001(11) _refine_ls_number_reflns 1949 _refine_ls_number_parameters 203 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0213 _refine_ls_R_factor_gt 0.0201 _refine_ls_wR_factor_ref 0.0540 _refine_ls_wR_factor_gt 0.0530 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.003 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.05733(4) 0.112972(9) 0.78349(3) 0.01473(10) Uani 1 1 d . . . O1 O 0.3689(5) 0.32825(11) 1.1831(2) 0.0206(6) Uani 1 1 d . . . O2 O 0.6840(5) 0.33995(9) 1.0723(3) 0.0402(6) Uani 1 1 d . . . O3 O -0.7038(4) -0.05916(8) 0.3739(2) 0.0199(5) Uani 1 1 d . . . O4 O -0.3099(4) -0.09977(8) 0.3763(2) 0.0213(4) Uani 1 1 d . . . N1 N 0.2059(5) 0.17377(12) 0.8935(3) 0.0184(7) Uani 1 1 d . . . N2 N -0.1041(5) 0.05543(11) 0.6661(2) 0.0176(6) Uani 1 1 d . . . C1 C 0.0989(7) 0.18937(14) 0.9868(3) 0.0241(8) Uani 1 1 d . . . H1 H -0.0411 0.1686 1.0070 0.029 Uiso 1 1 calc R . . C2 C 0.1829(7) 0.23468(13) 1.0559(4) 0.0231(8) Uani 1 1 d . . . H2 H 0.1034 0.2439 1.1220 0.028 Uiso 1 1 calc R . . C3 C 0.3858(6) 0.26599(13) 1.0259(3) 0.0196(7) Uani 1 1 d . . . C4 C 0.4981(5) 0.25008(11) 0.9279(3) 0.0223(6) Uani 1 1 d . . . H4 H 0.6371 0.2704 0.9056 0.027 Uiso 1 1 calc R . . C5 C 0.4051(5) 0.20433(11) 0.8635(3) 0.0213(6) Uani 1 1 d . . . H5 H 0.4817 0.1941 0.7972 0.026 Uiso 1 1 calc R . . C6 C 0.4898(6) 0.31583(13) 1.0981(3) 0.0210(8) Uani 1 1 d . . . C7 C -0.3418(6) 0.06380(10) 0.5981(3) 0.0206(6) Uani 1 1 d . . . H7 H -0.4313 0.0964 0.6078 0.025 Uiso 1 1 calc R . . C8 C -0.4620(6) 0.02665(11) 0.5141(3) 0.0222(6) Uani 1 1 d . . . H8 H -0.6308 0.0338 0.4692 0.027 Uiso 1 1 calc R . . C9 C -0.3305(5) -0.02149(11) 0.4966(3) 0.0176(6) Uani 1 1 d . . . C10 C -0.0827(5) -0.02991(11) 0.5663(3) 0.0220(6) Uani 1 1 d . . . H10 H 0.0132 -0.0617 0.5565 0.026 Uiso 1 1 calc R . . C11 C 0.0220(5) 0.00834(11) 0.6497(3) 0.0216(6) Uani 1 1 d . . . H11 H 0.1882 0.0015 0.6975 0.026 Uiso 1 1 calc R . . C12 C -0.4529(5) -0.06395(10) 0.4084(3) 0.0169(6) Uani 1 1 d . . . O5 O 0.7388(8) 0.37413(18) 0.8382(5) 0.0600(15) Uani 0.686(6) 1 d PG A -1 H5A H 0.7118 0.3624 0.9151 0.090 Uiso 0.686(6) 1 d PG A -1 C13 C 0.9914(17) 0.3531(5) 0.8147(9) 0.0555(18) Uani 0.686(6) 1 d PG A -1 H13A H 0.9698 0.3161 0.7879 0.067 Uiso 0.686(6) 1 d PG A -1 H13B H 1.1205 0.3538 0.8871 0.067 Uiso 0.686(6) 1 d PG A -1 C14 C 1.086(3) 0.3871(5) 0.7206(16) 0.080(3) Uani 0.686(6) 1 d PG A -1 H14A H 1.2522 0.3731 0.7054 0.119 Uiso 0.686(6) 1 d PG A -1 H14B H 0.9573 0.3859 0.6480 0.119 Uiso 0.686(6) 1 d PG A -1 H14C H 1.1093 0.4239 0.7481 0.119 Uiso 0.686(6) 1 d PG A -1 O5' O 0.272(2) 0.3508(4) 0.6937(10) 0.062 Uiso 0.314(6) 1 d PG A -2 H5' H 0.4370 0.3604 0.7411 0.093 Uiso 0.314(6) 1 d PG A -2 C13' C 0.060(6) 0.3829(10) 0.731(3) 0.065 Uiso 0.314(6) 1 d PG A -2 H13C H -0.0854 0.3862 0.6656 0.078 Uiso 0.314(6) 1 d PG A -2 H13D H 0.1248 0.4187 0.7537 0.078 Uiso 0.314(6) 1 d PG A -2 C14' C -0.031(6) 0.3558(16) 0.835(3) 0.072 Uiso 0.314(6) 1 d PG A -2 H14D H -0.1703 0.3771 0.8596 0.108 Uiso 0.314(6) 1 d PG A -2 H14E H -0.0974 0.3202 0.8120 0.108 Uiso 0.314(6) 1 d PG A -2 H14F H 0.1144 0.3529 0.9008 0.108 Uiso 0.314(6) 1 d PG 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 Cu 0.01740(15) 0.00963(13) 0.01504(16) 0.00005(18) -0.00312(10) 0.00021(17) O1 0.0252(13) 0.0160(11) 0.0194(14) -0.0038(10) 0.0003(10) -0.0002(9) O2 0.0351(13) 0.0331(12) 0.0554(18) -0.0226(12) 0.0163(12) -0.0180(11) O3 0.0204(11) 0.0134(10) 0.0224(13) -0.0020(9) -0.0059(10) 0.0005(8) O4 0.0205(9) 0.0174(9) 0.0262(12) -0.0044(8) 0.0044(9) 0.0009(8) N1 0.0205(14) 0.0126(13) 0.0206(17) -0.0019(12) -0.0009(12) -0.0003(11) N2 0.0184(13) 0.0137(12) 0.0197(15) -0.0022(10) 0.0005(11) -0.0001(10) C1 0.0238(17) 0.0229(17) 0.026(2) -0.0036(14) 0.0063(15) -0.0030(13) C2 0.0249(17) 0.0179(16) 0.026(2) -0.0087(14) 0.0044(14) -0.0024(13) C3 0.0200(16) 0.0166(16) 0.0203(18) -0.0024(14) -0.0021(13) 0.0037(11) C4 0.0206(14) 0.0153(13) 0.0307(19) -0.0023(12) 0.0038(12) -0.0026(10) C5 0.0221(14) 0.0182(13) 0.0233(16) -0.0022(11) 0.0027(12) -0.0004(11) C6 0.0188(16) 0.0107(14) 0.030(2) -0.0052(13) -0.0064(15) 0.0011(12) C7 0.0191(13) 0.0118(12) 0.0289(18) -0.0029(12) -0.0014(13) 0.0034(10) C8 0.0180(14) 0.0214(14) 0.0243(17) -0.0034(13) -0.0048(12) 0.0030(11) C9 0.0178(14) 0.0147(12) 0.0196(16) -0.0030(11) 0.0014(12) -0.0017(10) C10 0.0182(14) 0.0170(13) 0.0288(17) -0.0044(12) -0.0017(12) 0.0044(10) C11 0.0164(13) 0.0207(13) 0.0247(16) -0.0036(12) -0.0048(12) 0.0023(10) C12 0.0171(14) 0.0169(13) 0.0158(14) 0.0040(11) 0.0004(12) -0.0024(10) O5 0.048(3) 0.050(2) 0.082(4) 0.007(2) 0.014(2) -0.0020(19) C13 0.077(6) 0.057(4) 0.033(5) 0.008(4) 0.010(3) -0.009(3) C14 0.078(6) 0.095(7) 0.067(7) 0.027(5) 0.015(5) -0.016(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu O3 1.966(2) 2_655 ? Cu O1 1.984(3) 4_454 ? Cu N1 2.011(3) . ? Cu N2 2.019(3) . ? Cu O4 2.330(2) 2 ? O1 C6 1.269(4) . ? O1 Cu 1.984(3) 4 ? O2 C6 1.236(4) . ? O3 C12 1.281(3) . ? O3 Cu 1.966(2) 2_454 ? O4 C12 1.240(3) . ? O4 Cu 2.330(2) 2_554 ? N1 C1 1.328(5) . ? N1 C5 1.357(4) . ? N2 C7 1.338(4) . ? N2 C11 1.356(4) . ? C1 C2 1.388(5) . ? C2 C3 1.383(4) . ? C3 C4 1.392(5) . ? C3 C6 1.519(5) . ? C4 C5 1.381(4) . ? C7 C8 1.385(4) . ? C8 C9 1.394(4) . ? C9 C10 1.388(4) . ? C9 C12 1.506(4) . ? C10 C11 1.375(4) . ? O5 C13 1.4599 . ? C13 C14 1.5000 . ? O5' C13' 1.4599 . ? C13' C14' 1.5002 . ? 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 O3 Cu O1 170.63(11) 2_655 4_454 ? O3 Cu N1 92.60(11) 2_655 . ? O1 Cu N1 84.57(8) 4_454 . ? O3 Cu N2 90.92(8) 2_655 . ? O1 Cu N2 91.87(12) 4_454 . ? N1 Cu N2 176.44(12) . . ? O3 Cu O4 98.54(9) 2_655 2 ? O1 Cu O4 90.59(9) 4_454 2 ? N1 Cu O4 94.13(10) . 2 ? N2 Cu O4 85.93(9) . 2 ? C6 O1 Cu 111.0(2) . 4 ? C12 O3 Cu 126.61(18) . 2_454 ? C12 O4 Cu 142.63(18) . 2_554 ? C1 N1 C5 118.1(3) . . ? C1 N1 Cu 123.0(2) . . ? C5 N1 Cu 118.5(2) . . ? C7 N2 C11 117.4(3) . . ? C7 N2 Cu 119.9(2) . . ? C11 N2 Cu 122.7(2) . . ? N1 C1 C2 123.4(3) . . ? C3 C2 C1 118.8(3) . . ? C2 C3 C4 118.1(3) . . ? C2 C3 C6 121.7(3) . . ? C4 C3 C6 120.2(3) . . ? C5 C4 C3 119.9(3) . . ? N1 C5 C4 121.7(3) . . ? O2 C6 O1 125.6(3) . . ? O2 C6 C3 118.8(3) . . ? O1 C6 C3 115.6(3) . . ? N2 C7 C8 123.0(3) . . ? C7 C8 C9 119.4(3) . . ? C10 C9 C8 117.6(3) . . ? C10 C9 C12 120.5(2) . . ? C8 C9 C12 122.0(2) . . ? C11 C10 C9 119.8(3) . . ? N2 C11 C10 122.8(3) . . ? O4 C12 O3 126.0(3) . . ? O4 C12 C9 119.3(2) . . ? O3 C12 C9 114.7(2) . . ? O5 C13 C14 109.7 . . ? O5' C13' C14' 109.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Cu N1 C1 -94.2(3) 2_655 . . . ? O1 Cu N1 C1 94.8(3) 4_454 . . . ? N2 Cu N1 C1 95(2) . . . . ? O4 Cu N1 C1 4.6(3) 2 . . . ? O3 Cu N1 C5 93.7(2) 2_655 . . . ? O1 Cu N1 C5 -77.4(2) 4_454 . . . ? N2 Cu N1 C5 -77(2) . . . . ? O4 Cu N1 C5 -167.6(2) 2 . . . ? O3 Cu N2 C7 160.4(3) 2_655 . . . ? O1 Cu N2 C7 -28.6(3) 4_454 . . . ? N1 Cu N2 C7 -29(2) . . . . ? O4 Cu N2 C7 61.9(2) 2 . . . ? O3 Cu N2 C11 -21.7(3) 2_655 . . . ? O1 Cu N2 C11 149.4(2) 4_454 . . . ? N1 Cu N2 C11 149(2) . . . . ? O4 Cu N2 C11 -120.2(3) 2 . . . ? C5 N1 C1 C2 -1.0(5) . . . . ? Cu N1 C1 C2 -173.2(3) . . . . ? N1 C1 C2 C3 1.0(5) . . . . ? C1 C2 C3 C4 -0.7(4) . . . . ? C1 C2 C3 C6 -179.4(4) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C6 C3 C4 C5 179.1(3) . . . . ? C1 N1 C5 C4 0.7(5) . . . . ? Cu N1 C5 C4 173.2(2) . . . . ? C3 C4 C5 N1 -0.4(4) . . . . ? Cu O1 C6 O2 -6.7(4) 4 . . . ? Cu O1 C6 C3 171.7(2) 4 . . . ? C2 C3 C6 O2 174.8(3) . . . . ? C4 C3 C6 O2 -3.9(5) . . . . ? C2 C3 C6 O1 -3.7(4) . . . . ? C4 C3 C6 O1 177.6(3) . . . . ? C11 N2 C7 C8 0.6(5) . . . . ? Cu N2 C7 C8 178.6(3) . . . . ? N2 C7 C8 C9 -1.2(5) . . . . ? C7 C8 C9 C10 0.5(5) . . . . ? C7 C8 C9 C12 178.8(3) . . . . ? C8 C9 C10 C11 0.8(5) . . . . ? C12 C9 C10 C11 -177.5(3) . . . . ? C7 N2 C11 C10 0.8(5) . . . . ? Cu N2 C11 C10 -177.2(2) . . . . ? C9 C10 C11 N2 -1.5(5) . . . . ? Cu O4 C12 O3 121.0(3) 2_554 . . . ? Cu O4 C12 C9 -59.6(4) 2_554 . . . ? Cu O3 C12 O4 11.2(4) 2_454 . . . ? Cu O3 C12 C9 -168.31(19) 2_454 . . . ? C10 C9 C12 O4 -17.7(4) . . . . ? C8 C9 C12 O4 164.0(3) . . . . ? C10 C9 C12 O3 161.8(3) . . . . ? C8 C9 C12 O3 -16.5(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 O5 H5A O2 0.95 1.89 2.841(6) 175.9 . O5' H5' O5 0.95 1.77 2.714(12) 175.1 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.259 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.046 data_Spiral_complex_5 _database_code_CSD 169211 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 N2 O4 Cu, 0.75 C3 H8 O' _chemical_formula_sum 'C14.25 H14 N2 O4.75 Cu' _chemical_formula_weight 352.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 5.1646(4) _cell_length_b 24.4660(17) _cell_length_c 11.5850(8) _cell_angle_alpha 90.00 _cell_angle_beta 101.559(1) _cell_angle_gamma 90.00 _cell_volume 1434.16(18) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3127 _cell_measurement_theta_min 1.66 _cell_measurement_theta_max 25.00 _exptl_crystal_description 'Prismatic block' _exptl_crystal_colour Blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 722 _exptl_absorpt_coefficient_mu 1.547 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.6246 _exptl_absorpt_correction_T_max 0.9208 _exptl_absorpt_process_details ? _diffrn_ambient_temperature 223(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 'Siemens SMART CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 1K _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 3756 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2409 _reflns_number_gt 2206 _reflns_threshold_expression >4sigma(I) _computing_data_collection 'Siemens SMART software (Siemens, 1996)' _computing_cell_refinement 'Bruker SAINT software (Bruker, 1999)' _computing_data_reduction 'Bruker SAINT software (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0458P)^2^+1.4661P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.017(13) _refine_ls_number_reflns 2362 _refine_ls_number_parameters 223 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0279 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0675 _refine_ls_wR_factor_gt 0.0659 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.255 _refine_ls_shift/su_mean 0.017 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.05799(6) 0.113434(11) 0.78326(4) 0.01708(11) Uani 1 1 d . . . O1 O 0.3665(6) 0.32696(13) 1.1861(2) 0.0234(7) Uani 1 1 d . . . O2 O 0.6892(6) 0.33814(11) 1.0871(3) 0.0469(7) Uani 1 1 d . . . O3 O -0.7059(5) -0.05855(10) 0.3715(2) 0.0223(6) Uani 1 1 d . . . O4 O -0.3117(5) -0.09770(9) 0.3739(2) 0.0243(5) Uani 1 1 d . . . N1 N 0.2092(7) 0.17358(15) 0.8953(3) 0.0212(8) Uani 1 1 d . . . N2 N -0.1065(6) 0.05659(13) 0.6646(3) 0.0205(7) Uani 1 1 d . . . C1 C 0.1000(9) 0.18844(17) 0.9850(4) 0.0299(10) Uani 1 1 d . . . H1 H -0.0409 0.1675 1.0014 0.036 Uiso 1 1 calc R . . C2 C 0.1840(8) 0.23337(17) 1.0555(4) 0.0283(10) Uani 1 1 d . . . H2 H 0.1032 0.2421 1.1189 0.034 Uiso 1 1 calc R . . C3 C 0.3870(7) 0.26496(17) 1.0315(3) 0.0244(9) Uani 1 1 d . . . C4 C 0.5017(7) 0.24987(14) 0.9370(3) 0.0276(8) Uani 1 1 d . . . H4 H 0.6416 0.2705 0.9186 0.033 Uiso 1 1 calc R . . C5 C 0.4087(7) 0.20445(13) 0.8705(3) 0.0255(7) Uani 1 1 d . . . H5 H 0.4858 0.1948 0.8064 0.031 Uiso 1 1 calc R . . C6 C 0.4894(8) 0.31460(17) 1.1061(4) 0.0262(9) Uani 1 1 d . . . C7 C -0.3474(7) 0.06405(13) 0.5994(3) 0.0271(7) Uani 1 1 d . . . H7 H -0.4402 0.0960 0.6109 0.033 Uiso 1 1 calc R . . C8 C -0.4665(7) 0.02697(14) 0.5160(3) 0.0269(7) Uani 1 1 d . . . H8 H -0.6387 0.0334 0.4733 0.032 Uiso 1 1 calc R . . C9 C -0.3310(6) -0.02008(13) 0.4949(3) 0.0201(7) Uani 1 1 d . . . C10 C -0.0812(7) -0.02705(14) 0.5600(3) 0.0313(8) Uani 1 1 d . . . H10 H 0.0183 -0.0579 0.5476 0.038 Uiso 1 1 calc R . . C11 C 0.0251(7) 0.01145(15) 0.6442(3) 0.0310(8) Uani 1 1 d . . . H11 H 0.1960 0.0057 0.6888 0.037 Uiso 1 1 calc R . . C12 C -0.4554(6) -0.06266(12) 0.4058(3) 0.0193(7) Uani 1 1 d . . . O5 O 0.704(3) 0.3742(9) 0.8705(18) 0.073(2) Uiso 0.269(5) 1 d PD A -1 H5A H 0.6610 0.3622 0.9433 0.109 Uiso 0.269(5) 1 d P A -1 C13 C 0.957(4) 0.3565(11) 0.847(2) 0.073(2) Uiso 0.269(5) 1 d PD A -1 H13A H 0.9414 0.3182 0.8217 0.087 Uiso 0.269(5) 1 calc PR A -1 H13B H 1.0889 0.3583 0.9203 0.087 Uiso 0.269(5) 1 calc PR A -1 C14 C 1.056(4) 0.3894(10) 0.7540(18) 0.073(2) Uiso 0.269(5) 1 d PD A -1 H14A H 1.0663 0.4282 0.7755 0.087 Uiso 0.269(5) 1 calc PR A -1 H14B H 0.9353 0.3855 0.6777 0.087 Uiso 0.269(5) 1 calc PR A -1 C15 C 1.329(4) 0.3684(11) 0.746(2) 0.073(2) Uiso 0.269(5) 1 d PD A -1 H15A H 1.4097 0.3932 0.6978 0.109 Uiso 0.269(5) 1 calc PR A -1 H15B H 1.3132 0.3324 0.7098 0.109 Uiso 0.269(5) 1 calc PR A -1 H15C H 1.4388 0.3662 0.8240 0.109 Uiso 0.269(5) 1 calc PR A -1 O6 O 0.259(3) 0.3518(6) 0.6977(14) 0.073(2) Uiso 0.269(5) 1 d PD A -2 H6A H 0.4104 0.3605 0.7563 0.109 Uiso 0.269(5) 1 calc PR A -2 C16 C 0.036(4) 0.3852(9) 0.715(2) 0.073(2) Uiso 0.269(5) 1 d PD A -2 H16A H -0.0976 0.3870 0.6420 0.087 Uiso 0.269(5) 1 calc PR A -2 H16B H 0.0951 0.4224 0.7379 0.087 Uiso 0.269(5) 1 calc PR A -2 C17 C -0.080(4) 0.3590(11) 0.811(2) 0.073(2) Uiso 0.269(5) 1 d PD A -2 H17A H 0.0122 0.3722 0.8886 0.087 Uiso 0.269(5) 1 calc PR A -2 H17B H -0.0588 0.3192 0.8094 0.087 Uiso 0.269(5) 1 calc PR A -2 C18 C -0.370(3) 0.3735(11) 0.792(3) 0.073(2) Uiso 0.269(5) 1 d PD A -2 H18A H -0.4452 0.3585 0.8560 0.109 Uiso 0.269(5) 1 calc PR A -2 H18B H -0.4622 0.3584 0.7179 0.109 Uiso 0.269(5) 1 calc PR A -2 H18C H -0.3902 0.4130 0.7909 0.109 Uiso 0.269(5) 1 calc PR A -2 O7 O -1.580(6) 0.3985(15) 0.831(3) 0.073(2) Uiso 0.112(4) 1 d PD B -3 C19 C -1.309(8) 0.378(3) 0.845(4) 0.073(2) Uiso 0.112(4) 1 d PD B -3 H19A H -1.2970 0.3417 0.8794 0.087 Uiso 0.112(4) 1 calc PR B -3 H19B H -1.1896 0.4024 0.8989 0.087 Uiso 0.112(4) 1 calc PR B -3 C20 C -1.226(7) 0.377(2) 0.727(4) 0.073(2) Uiso 0.112(4) 1 d PD B -3 H20A H -1.1812 0.3390 0.7096 0.087 Uiso 0.112(4) 1 calc PR B -3 H20B H -1.3720 0.3889 0.6651 0.087 Uiso 0.112(4) 1 calc PR B -3 C21 C -0.990(10) 0.413(2) 0.730(5) 0.073(2) Uiso 0.112(4) 1 d PD B -3 H21A H -0.9376 0.4115 0.6538 0.109 Uiso 0.112(4) 1 calc PR B -3 H21B H -0.8446 0.4005 0.7905 0.109 Uiso 0.112(4) 1 calc PR B -3 H21C H -1.0350 0.4502 0.7461 0.109 Uiso 0.112(4) 1 calc PR B -3 O8 O 2.704(7) 0.376(2) 0.803(5) 0.073(2) Uiso 0.112(4) 1 d PD B -4 C22 C 2.444(8) 0.380(2) 0.727(4) 0.073(2) Uiso 0.112(4) 1 d PD B -4 H22A H 2.4050 0.3462 0.6821 0.087 Uiso 0.112(4) 1 calc PR B -4 H22B H 2.4446 0.4101 0.6707 0.087 Uiso 0.112(4) 1 calc PR B -4 C23 C 2.231(7) 0.3905(16) 0.797(5) 0.073(2) Uiso 0.112(4) 1 d PD B -4 H23A H 2.1380 0.4245 0.7709 0.087 Uiso 0.112(4) 1 calc PR B -4 H23B H 2.3113 0.3941 0.8809 0.087 Uiso 0.112(4) 1 calc PR B -4 C24 C 2.039(10) 0.3430(17) 0.779(6) 0.073(2) Uiso 0.112(4) 1 d PD B -4 H24A H 1.9134 0.3473 0.8301 0.109 Uiso 0.112(4) 1 calc PR B -4 H24B H 2.1358 0.3091 0.7976 0.109 Uiso 0.112(4) 1 calc PR B -4 H24C H 1.9461 0.3423 0.6975 0.109 Uiso 0.112(4) 1 calc PR B -4 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.02230(17) 0.00929(16) 0.01640(16) 0.0001(2) -0.00391(11) 0.0004(2) O1 0.0322(16) 0.0169(15) 0.0187(13) -0.0035(11) -0.0007(11) -0.0001(11) O2 0.0408(16) 0.0402(16) 0.0635(19) -0.0285(15) 0.0194(14) -0.0205(14) O3 0.0246(13) 0.0138(12) 0.0243(13) -0.0017(10) -0.0048(10) -0.0002(10) O4 0.0275(12) 0.0191(11) 0.0258(12) -0.0068(9) 0.0042(10) -0.0009(10) N1 0.0266(17) 0.0129(18) 0.0217(18) -0.0027(14) -0.0006(14) 0.0002(14) N2 0.0239(16) 0.0146(15) 0.0208(15) -0.0025(12) -0.0008(12) -0.0005(12) C1 0.032(2) 0.024(2) 0.034(2) -0.0059(17) 0.0089(18) -0.0057(17) C2 0.030(2) 0.023(2) 0.033(2) -0.0126(17) 0.0069(17) -0.0067(17) C3 0.026(2) 0.020(2) 0.025(2) -0.0073(16) -0.0002(16) 0.0024(14) C4 0.0298(19) 0.0185(17) 0.034(2) -0.0036(14) 0.0052(15) -0.0056(14) C5 0.0302(18) 0.0171(16) 0.0289(17) -0.0030(13) 0.0049(14) -0.0005(14) C6 0.0222(19) 0.014(2) 0.037(2) -0.0052(16) -0.0064(18) -0.0039(15) C7 0.0261(17) 0.0142(16) 0.036(2) -0.0063(14) -0.0045(15) 0.0058(13) C8 0.0206(17) 0.0211(18) 0.0343(19) -0.0058(15) -0.0062(14) 0.0030(13) C9 0.0226(17) 0.0148(15) 0.0220(16) -0.0010(12) 0.0021(13) -0.0024(12) C10 0.0276(19) 0.0238(18) 0.037(2) -0.0133(15) -0.0065(15) 0.0069(14) C11 0.0240(17) 0.0279(18) 0.035(2) -0.0117(15) -0.0090(14) 0.0073(14) C12 0.0264(18) 0.0134(15) 0.0164(15) 0.0018(12) 0.0002(13) -0.0014(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu O3 1.958(2) 2_655 ? Cu O1 1.981(3) 4_454 ? Cu N1 2.014(3) . ? Cu N2 2.019(3) . ? Cu O4 2.387(2) 2 ? O1 C6 1.261(5) . ? O1 Cu 1.981(3) 4 ? O2 C6 1.239(5) . ? O3 C12 1.279(4) . ? O3 Cu 1.958(2) 2_454 ? O4 C12 1.238(4) . ? O4 Cu 2.387(2) 2_554 ? N1 C1 1.328(6) . ? N1 C5 1.354(5) . ? N2 C7 1.332(5) . ? N2 C11 1.342(5) . ? C1 C2 1.386(6) . ? C2 C3 1.374(5) . ? C3 C4 1.396(5) . ? C3 C6 1.522(6) . ? C4 C5 1.382(5) . ? C7 C8 1.378(5) . ? C8 C9 1.394(5) . ? C9 C10 1.368(5) . ? C9 C12 1.516(4) . ? C10 C11 1.388(5) . ? O5 C13 1.453(10) . ? C13 C14 1.512(10) . ? C14 C15 1.521(10) . ? O6 C16 1.462(10) . ? C16 C17 1.510(10) . ? C17 C18 1.515(10) . ? O7 C19 1.460(10) . ? C19 C20 1.512(10) . ? C20 C21 1.503(10) . ? O8 C22 1.454(10) . ? C22 C23 1.513(10) . ? C23 C24 1.514(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 O3 Cu O1 171.46(12) 2_655 4_454 ? O3 Cu N1 92.52(13) 2_655 . ? O1 Cu N1 85.02(9) 4_454 . ? O3 Cu N2 90.92(9) 2_655 . ? O1 Cu N2 91.51(14) 4_454 . ? N1 Cu N2 176.53(15) . . ? O3 Cu O4 97.42(10) 2_655 2 ? O1 Cu O4 90.93(10) 4_454 2 ? N1 Cu O4 94.32(12) . 2 ? N2 Cu O4 85.64(11) . 2 ? C6 O1 Cu 109.1(3) . 4 ? C12 O3 Cu 126.4(2) . 2_454 ? C12 O4 Cu 145.4(2) . 2_554 ? C1 N1 C5 118.3(4) . . ? C1 N1 Cu 122.2(3) . . ? C5 N1 Cu 119.0(3) . . ? C7 N2 C11 117.5(3) . . ? C7 N2 Cu 120.6(2) . . ? C11 N2 Cu 121.9(3) . . ? N1 C1 C2 123.1(4) . . ? C3 C2 C1 119.3(4) . . ? C2 C3 C4 118.1(3) . . ? C2 C3 C6 121.8(3) . . ? C4 C3 C6 120.2(4) . . ? C5 C4 C3 119.7(3) . . ? N1 C5 C4 121.6(3) . . ? O2 C6 O1 125.4(4) . . ? O2 C6 C3 118.5(4) . . ? O1 C6 C3 116.1(4) . . ? N2 C7 C8 122.8(3) . . ? C7 C8 C9 119.8(3) . . ? C10 C9 C8 117.2(3) . . ? C10 C9 C12 120.9(3) . . ? C8 C9 C12 121.8(3) . . ? C9 C10 C11 120.0(3) . . ? N2 C11 C10 122.6(3) . . ? O4 C12 O3 126.2(3) . . ? O4 C12 C9 118.8(3) . . ? O3 C12 C9 115.0(3) . . ? O5 C13 C14 115.1(16) . . ? C13 C14 C15 108.5(9) . . ? O6 C16 C17 107.8(16) . . ? C16 C17 C18 108.6(10) . . ? O7 C19 C20 110.6(11) . . ? C21 C20 C19 110.0(10) . . ? O8 C22 C23 111.5(11) . . ? C22 C23 C24 108.9(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 O3 Cu N1 C1 -95.0(3) 2_655 . . . ? O1 Cu N1 C1 93.2(3) 4_454 . . . ? N2 Cu N1 C1 92(3) . . . . ? O4 Cu N1 C1 2.6(3) 2 . . . ? O3 Cu N1 C5 93.4(3) 2_655 . . . ? O1 Cu N1 C5 -78.4(3) 4_454 . . . ? N2 Cu N1 C5 -80(3) . . . . ? O4 Cu N1 C5 -169.0(3) 2 . . . ? O3 Cu N2 C7 157.4(3) 2_655 . . . ? O1 Cu N2 C7 -30.8(3) 4_454 . . . ? N1 Cu N2 C7 -29(3) . . . . ? O4 Cu N2 C7 60.1(3) 2 . . . ? O3 Cu N2 C11 -25.7(3) 2_655 . . . ? O1 Cu N2 C11 146.1(3) 4_454 . . . ? N1 Cu N2 C11 147(2) . . . . ? O4 Cu N2 C11 -123.1(3) 2 . . . ? C5 N1 C1 C2 -1.3(7) . . . . ? Cu N1 C1 C2 -173.0(3) . . . . ? N1 C1 C2 C3 1.0(6) . . . . ? C1 C2 C3 C4 -0.6(5) . . . . ? C1 C2 C3 C6 -179.6(5) . . . . ? C2 C3 C4 C5 0.4(5) . . . . ? C6 C3 C4 C5 179.5(3) . . . . ? C1 N1 C5 C4 1.1(6) . . . . ? Cu N1 C5 C4 173.0(3) . . . . ? C3 C4 C5 N1 -0.6(5) . . . . ? Cu O1 C6 O2 -3.8(5) 4 . . . ? Cu O1 C6 C3 173.2(3) 4 . . . ? C2 C3 C6 O2 173.0(4) . . . . ? C4 C3 C6 O2 -6.0(6) . . . . ? C2 C3 C6 O1 -4.3(5) . . . . ? C4 C3 C6 O1 176.7(4) . . . . ? C11 N2 C7 C8 1.9(6) . . . . ? Cu N2 C7 C8 178.9(3) . . . . ? N2 C7 C8 C9 -1.7(6) . . . . ? C7 C8 C9 C10 0.1(6) . . . . ? C7 C8 C9 C12 178.7(3) . . . . ? C8 C9 C10 C11 1.1(6) . . . . ? C12 C9 C10 C11 -177.5(3) . . . . ? C7 N2 C11 C10 -0.6(6) . . . . ? Cu N2 C11 C10 -177.6(3) . . . . ? C9 C10 C11 N2 -0.9(6) . . . . ? Cu O4 C12 O3 121.2(4) 2_554 . . . ? Cu O4 C12 C9 -59.4(5) 2_554 . . . ? Cu O3 C12 O4 12.4(5) 2_454 . . . ? Cu O3 C12 C9 -167.0(2) 2_454 . . . ? C10 C9 C12 O4 -15.5(5) . . . . ? C8 C9 C12 O4 165.9(4) . . . . ? C10 C9 C12 O3 164.0(3) . . . . ? C8 C9 C12 O3 -14.6(5) . . . . ? O5 C13 C14 C15 176(2) . . . . ? O6 C16 C17 C18 -153(2) . . . . ? O7 C19 C20 C21 120(5) . . . . ? O8 C22 C23 C24 -118(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 O5 H5A O2 0.96 1.75 2.68(2) 162.1 . O6 H6A O5 0.95 1.83 2.78(3) 177.6 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.286 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.050