# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'RSC Advances' _journal_coden_Cambridge 1500 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Goutam Lahiri' _publ_contact_author_email lahiri@chem.iitb.ac.in _publ_section_title ; Varying structural motifs in oxyanions (NO3 CO3) and phenoxyacetate (PhOAcbridged coordination polymers derived from alkoxo-bridged dicopper building blocks with {Cu2O2} core ; _publ_author_name G.Lahiri # Attachment '- 1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 657305' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H8 Cu N2 O4' _chemical_formula_weight 247.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.5980(5) _cell_length_b 4.7885(2) _cell_length_c 14.5449(8) _cell_angle_alpha 90.00 _cell_angle_beta 112.389(5) _cell_angle_gamma 90.00 _cell_volume 875.69(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5390 _cell_measurement_theta_min 3.0007 _cell_measurement_theta_max 32.4618 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.879 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 2.482 _exptl_absorpt_correction_T_min 0.4857 _exptl_absorpt_correction_T_max 0.5230 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5299 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0141 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1539 _reflns_number_gt 1407 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0298P)^2^+0.5813P] 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 RIDING _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1539 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0226 _refine_ls_R_factor_gt 0.0199 _refine_ls_wR_factor_ref 0.0539 _refine_ls_wR_factor_gt 0.0529 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 0.540951(17) 0.06992(5) 0.421817(16) 0.01536(10) Uani 1 1 d . . . O1 O 0.40893(10) 0.0228(3) 0.43881(10) 0.0175(3) Uani 1 1 d . . . O2 O 0.47716(11) 0.2160(3) 0.28169(10) 0.0201(3) Uani 1 1 d . . . O3 O 0.53092(12) -0.4060(3) 0.36829(11) 0.0255(4) Uani 1 1 d . . . O4 O 0.46607(13) 0.6126(3) 0.20680(11) 0.0293(4) Uani 1 1 d . . . N1 N 0.68771(13) 0.1177(4) 0.42784(12) 0.0183(4) Uani 1 1 d . . . N2 N 0.49121(13) 0.4810(4) 0.28457(12) 0.0178(4) Uani 1 1 d . . . C1 C 0.71515(18) 0.0257(5) 0.35386(16) 0.0244(5) Uani 1 1 d . . . H1 H 0.6632 -0.0670 0.2991 0.029 Uiso 1 1 calc R . . C2 C 0.81578(19) 0.0605(5) 0.35439(18) 0.0296(5) Uani 1 1 d . . . H2 H 0.8333 -0.0086 0.3013 0.036 Uiso 1 1 calc R . . C3 C 0.89102(17) 0.1983(6) 0.43393(17) 0.0319(5) Uani 1 1 d . . . H3 H 0.9606 0.2295 0.4355 0.038 Uiso 1 1 calc R . . C4 C 0.86355(16) 0.2895(5) 0.51071(16) 0.0271(5) Uani 1 1 d . . . H4 H 0.9148 0.3813 0.5663 0.033 Uiso 1 1 calc R . . C5 C 0.76083(15) 0.2475(4) 0.50699(14) 0.0200(4) Uani 1 1 d . . . C6 C 0.72690(15) 0.3353(4) 0.58929(14) 0.0205(4) Uani 1 1 d . . . H6A H 0.6702 0.4779 0.5638 0.025 Uiso 1 1 calc R . . H6B H 0.7881 0.4221 0.6430 0.025 Uiso 1 1 calc R . . C7 C 0.31419(16) -0.0914(4) 0.36793(14) 0.0188(4) Uani 1 1 d . . . H7B H 0.3279 -0.1562 0.3093 0.023 Uiso 1 1 calc R . . H7A H 0.2590 0.0558 0.3455 0.023 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01428(14) 0.01774(15) 0.01258(14) -0.00027(9) 0.00346(10) -0.00081(9) O1 0.0139(7) 0.0232(7) 0.0137(7) -0.0012(6) 0.0035(6) -0.0025(6) O2 0.0240(7) 0.0147(7) 0.0176(7) -0.0005(6) 0.0036(5) -0.0038(6) O3 0.0326(8) 0.0191(8) 0.0192(8) -0.0048(6) 0.0035(6) 0.0002(6) O4 0.0421(9) 0.0248(8) 0.0204(8) 0.0075(6) 0.0111(7) 0.0011(7) N1 0.0180(8) 0.0192(9) 0.0177(8) 0.0009(7) 0.0069(7) 0.0000(7) N2 0.0153(8) 0.0200(9) 0.0185(9) 0.0012(7) 0.0070(7) 0.0014(7) C1 0.0270(11) 0.0258(11) 0.0218(11) 0.0001(9) 0.0110(9) 0.0006(9) C2 0.0321(12) 0.0336(13) 0.0308(12) 0.0043(10) 0.0207(10) 0.0038(10) C3 0.0200(10) 0.0430(15) 0.0352(13) 0.0119(11) 0.0133(9) -0.0017(10) C4 0.0186(10) 0.0327(13) 0.0262(11) 0.0069(10) 0.0043(9) -0.0043(10) C5 0.0192(9) 0.0180(10) 0.0195(10) 0.0045(8) 0.0035(8) -0.0002(8) C6 0.0171(9) 0.0206(10) 0.0186(10) -0.0037(8) 0.0010(8) -0.0028(9) C7 0.0152(9) 0.0235(11) 0.0138(9) 0.0002(8) 0.0013(7) -0.0005(8) _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 1.9165(14) . ? Cu1 O1 1.9284(13) 3_656 ? Cu1 N1 1.9772(17) . ? Cu1 O2 2.0123(14) . ? Cu1 O3 2.3953(14) . ? Cu1 Cu1 2.9649(5) 3_656 ? O1 C7 1.418(2) . ? O1 Cu1 1.9284(13) 3_656 ? O2 N2 1.281(2) . ? O3 N2 1.252(2) 1_545 ? O4 N2 1.224(2) . ? N1 C1 1.341(3) . ? N1 C5 1.352(3) . ? N2 O3 1.252(2) 1_565 ? C1 C2 1.376(3) . ? C1 H1 0.9500 . ? C2 C3 1.385(3) . ? C2 H2 0.9500 . ? C3 C4 1.377(3) . ? C3 H3 0.9500 . ? C4 C5 1.392(3) . ? C4 H4 0.9500 . ? C5 C6 1.498(3) . ? C6 C7 1.526(3) 3_656 ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C6 1.526(3) 3_656 ? C7 H7B 0.9900 . ? C7 H7A 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 79.08(6) . 3_656 ? O1 Cu1 N1 170.80(6) . . ? O1 Cu1 N1 91.92(6) 3_656 . ? O1 Cu1 O2 96.20(6) . . ? O1 Cu1 O2 171.20(6) 3_656 . ? N1 Cu1 O2 92.46(6) . . ? O1 Cu1 O3 89.42(6) . . ? O1 Cu1 O3 94.36(6) 3_656 . ? N1 Cu1 O3 93.22(6) . . ? O2 Cu1 O3 93.00(5) . . ? O1 Cu1 Cu1 39.69(4) . 3_656 ? O1 Cu1 Cu1 39.40(4) 3_656 3_656 ? N1 Cu1 Cu1 131.29(5) . 3_656 ? O2 Cu1 Cu1 135.44(4) . 3_656 ? O3 Cu1 Cu1 92.46(4) . 3_656 ? C7 O1 Cu1 126.02(12) . . ? C7 O1 Cu1 122.34(12) . 3_656 ? Cu1 O1 Cu1 100.92(6) . 3_656 ? N2 O2 Cu1 108.04(11) . . ? N2 O3 Cu1 132.66(12) 1_545 . ? C1 N1 C5 119.69(18) . . ? C1 N1 Cu1 120.74(14) . . ? C5 N1 Cu1 119.57(14) . . ? O4 N2 O3 122.80(17) . 1_565 ? O4 N2 O2 119.58(17) . . ? O3 N2 O2 117.62(16) 1_565 . ? N1 C1 C2 122.4(2) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C1 C2 C3 118.6(2) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 119.1(2) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 120.1(2) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? N1 C5 C4 120.1(2) . . ? N1 C5 C6 117.32(18) . . ? C4 C5 C6 122.58(18) . . ? C5 C6 C7 112.51(18) . 3_656 ? C5 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 3_656 . ? C5 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 3_656 . ? H6A C6 H6B 107.8 . . ? O1 C7 C6 111.79(16) . 3_656 ? O1 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 3_656 . ? O1 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 3_656 . ? H7B C7 H7A 107.9 . . ? 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 O1 Cu1 O1 C7 -144.47(18) 3_656 . . . ? N1 Cu1 O1 C7 -156.7(4) . . . . ? O2 Cu1 O1 C7 43.05(16) . . . . ? O3 Cu1 O1 C7 -49.91(15) . . . . ? Cu1 Cu1 O1 C7 -144.47(18) 3_656 . . . ? O1 Cu1 O1 Cu1 0.0 3_656 . . 3_656 ? N1 Cu1 O1 Cu1 -12.2(4) . . . 3_656 ? O2 Cu1 O1 Cu1 -172.49(6) . . . 3_656 ? O3 Cu1 O1 Cu1 94.56(6) . . . 3_656 ? O1 Cu1 O2 N2 103.09(12) . . . . ? O1 Cu1 O2 N2 46.0(4) 3_656 . . . ? N1 Cu1 O2 N2 -73.82(13) . . . . ? O3 Cu1 O2 N2 -167.17(12) . . . . ? Cu1 Cu1 O2 N2 96.25(12) 3_656 . . . ? O1 Cu1 O3 N2 90.26(18) . . . 1_545 ? O1 Cu1 O3 N2 169.26(17) 3_656 . . 1_545 ? N1 Cu1 O3 N2 -98.56(18) . . . 1_545 ? O2 Cu1 O3 N2 -5.92(18) . . . 1_545 ? Cu1 Cu1 O3 N2 129.84(17) 3_656 . . 1_545 ? O1 Cu1 N1 C1 151.7(4) . . . . ? O1 Cu1 N1 C1 139.78(16) 3_656 . . . ? O2 Cu1 N1 C1 -47.86(17) . . . . ? O3 Cu1 N1 C1 45.29(16) . . . . ? Cu1 Cu1 N1 C1 141.41(14) 3_656 . . . ? O1 Cu1 N1 C5 -29.0(5) . . . . ? O1 Cu1 N1 C5 -40.95(16) 3_656 . . . ? O2 Cu1 N1 C5 131.42(15) . . . . ? O3 Cu1 N1 C5 -135.43(15) . . . . ? Cu1 Cu1 N1 C5 -39.31(18) 3_656 . . . ? Cu1 O2 N2 O4 174.31(14) . . . . ? Cu1 O2 N2 O3 -5.5(2) . . . 1_565 ? C5 N1 C1 C2 -0.7(3) . . . . ? Cu1 N1 C1 C2 178.56(17) . . . . ? N1 C1 C2 C3 -0.7(3) . . . . ? C1 C2 C3 C4 1.6(4) . . . . ? C2 C3 C4 C5 -1.2(4) . . . . ? C1 N1 C5 C4 1.1(3) . . . . ? Cu1 N1 C5 C4 -178.14(15) . . . . ? C1 N1 C5 C6 -177.54(18) . . . . ? Cu1 N1 C5 C6 3.2(2) . . . . ? C3 C4 C5 N1 -0.2(3) . . . . ? C3 C4 C5 C6 178.4(2) . . . . ? N1 C5 C6 C7 57.2(2) . . . 3_656 ? C4 C5 C6 C7 -121.5(2) . . . 3_656 ? Cu1 O1 C7 C6 125.00(16) . . . 3_656 ? Cu1 O1 C7 C6 -12.5(2) 3_656 . . 3_656 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.319 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.058 # Attachment '- 3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 661088' #TrackingRef '- 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H24 Cu2 N2 O9' _chemical_formula_weight 503.44 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 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.0701(7) _cell_length_b 6.6051(3) _cell_length_c 15.6456(7) _cell_angle_alpha 90.00 _cell_angle_beta 104.807(4) _cell_angle_gamma 90.00 _cell_volume 1805.37(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3266 _cell_measurement_theta_min 2.9674 _cell_measurement_theta_max 32.4176 _exptl_crystal_description thin-plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.852 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 2.410 _exptl_absorpt_correction_T_min 0.6315 _exptl_absorpt_correction_T_max 0.9312 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7817 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1595 _reflns_number_gt 1278 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0654P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1595 _refine_ls_number_parameters 144 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0913 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 0.54885(2) 0.06527(7) 0.09077(3) 0.01131(19) Uani 1 1 d . . . O1 O 0.55518(14) -0.0658(4) -0.01651(19) 0.0164(6) Uani 1 1 d . . . O2 O 0.52292(14) 0.1966(4) 0.19119(18) 0.0117(6) Uani 1 1 d . . . O3 O 0.5000 -0.0993(6) 0.2500 0.0174(9) Uani 1 2 d S . . N1 N 0.66026(18) 0.0135(5) 0.1504(2) 0.0113(7) Uani 1 1 d . . . C1 C 0.6836(2) -0.0022(6) 0.2388(3) 0.0135(9) Uani 1 1 d . . . H1 H 0.6457 -0.0077 0.2712 0.016 Uiso 1 1 calc R . . C2 C 0.7593(2) -0.0106(6) 0.2850(3) 0.0163(9) Uani 1 1 d . . . H2 H 0.7732 -0.0206 0.3476 0.020 Uiso 1 1 calc R . . C3 C 0.8144(2) -0.0044(6) 0.2386(3) 0.0172(10) Uani 1 1 d . . . H3 H 0.8672 -0.0080 0.2687 0.021 Uiso 1 1 calc R . . C4 C 0.7915(2) 0.0072(6) 0.1479(3) 0.0160(9) Uani 1 1 d . . . H4 H 0.8288 0.0103 0.1147 0.019 Uiso 1 1 calc R . . C5 C 0.7142(2) 0.0144(6) 0.1044(3) 0.0100(8) Uani 1 1 d . . . C6 C 0.6882(2) 0.0224(6) 0.0051(3) 0.0136(9) Uani 1 1 d . . . H6A H 0.7326 -0.0054 -0.0194 0.016 Uiso 1 1 calc R . . H6B H 0.6698 0.1608 -0.0132 0.016 Uiso 1 1 calc R . . C7 C 0.6253(2) -0.1271(6) -0.0336(3) 0.0162(9) Uani 1 1 d . . . H7A H 0.6188 -0.1373 -0.0982 0.019 Uiso 1 1 calc R . . H7B H 0.6397 -0.2625 -0.0074 0.019 Uiso 1 1 calc R . . C8 C 0.5000 0.0931(8) 0.2500 0.0072(11) Uani 1 2 d S . . O111 O 0.58807(18) 0.3974(5) 0.0482(2) 0.0208(7) Uani 1 1 d . . . O222 O 0.48165(18) 0.5858(5) 0.1315(2) 0.0231(7) Uani 1 1 d . . . H111 H 0.489(3) 0.479(8) 0.154(3) 0.017(14) Uiso 1 1 d . . . H333 H 0.570(3) 0.416(7) -0.007(4) 0.021(13) Uiso 1 1 d . . . H222 H 0.495(3) 0.704(10) 0.170(4) 0.061(19) Uiso 1 1 d . . . H444 H 0.576(5) 0.514(12) 0.058(6) 0.09(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0095(3) 0.0160(3) 0.0084(3) -0.0018(2) 0.00241(18) 0.0007(2) O1 0.0091(13) 0.0237(16) 0.0160(16) -0.0072(13) 0.0026(11) 0.0019(12) O2 0.0122(12) 0.0129(15) 0.0114(15) 0.0016(12) 0.0056(11) -0.0003(11) O3 0.027(2) 0.012(2) 0.016(2) 0.000 0.0107(18) 0.000 N1 0.0127(16) 0.0123(17) 0.0094(18) 0.0003(13) 0.0036(14) 0.0004(13) C1 0.014(2) 0.014(2) 0.013(2) -0.0007(17) 0.0066(17) 0.0032(15) C2 0.022(2) 0.016(2) 0.009(2) 0.0011(17) 0.0008(18) 0.0038(17) C3 0.013(2) 0.015(2) 0.021(3) 0.0004(18) -0.0005(18) 0.0034(16) C4 0.0113(19) 0.018(2) 0.020(2) -0.0007(18) 0.0054(17) 0.0011(16) C5 0.0112(18) 0.0066(19) 0.013(2) -0.0009(16) 0.0036(16) -0.0010(15) C6 0.0112(19) 0.018(2) 0.014(2) 0.0006(17) 0.0056(16) 0.0012(16) C7 0.0143(19) 0.020(2) 0.015(2) -0.0035(18) 0.0045(17) 0.0018(17) C8 0.006(2) 0.009(3) 0.004(3) 0.000 -0.004(2) 0.000 O111 0.0233(16) 0.021(2) 0.0154(19) 0.0017(14) 0.0009(13) 0.0007(13) O222 0.0363(19) 0.0134(18) 0.0178(18) 0.0022(15) 0.0038(14) 0.0046(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.918(3) . ? Cu1 O1 1.941(3) 5_655 ? Cu1 O2 1.954(3) . ? Cu1 N1 2.020(3) . ? O1 C7 1.419(5) . ? O1 Cu1 1.941(3) 5_655 ? O2 C8 1.296(4) . ? O3 C8 1.271(6) . ? N1 C1 1.344(5) . ? N1 C5 1.351(5) . ? C1 C2 1.375(6) . ? C1 H1 0.9500 . ? C2 C3 1.374(6) . ? C2 H2 0.9500 . ? C3 C4 1.376(6) . ? C3 H3 0.9500 . ? C4 C5 1.391(5) . ? C4 H4 0.9500 . ? C5 C6 1.504(6) . ? C6 C7 1.511(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O2 1.296(4) 2_655 ? O111 H333 0.86(5) . ? O111 H444 0.82(8) . ? O222 H111 0.78(5) . ? O222 H222 0.98(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 75.06(12) . 5_655 ? O1 Cu1 O2 169.89(10) . . ? O1 Cu1 O2 94.93(11) 5_655 . ? O1 Cu1 N1 93.01(12) . . ? O1 Cu1 N1 167.23(13) 5_655 . ? O2 Cu1 N1 96.85(12) . . ? C7 O1 Cu1 123.3(2) . . ? C7 O1 Cu1 131.5(3) . 5_655 ? Cu1 O1 Cu1 104.94(12) . 5_655 ? C8 O2 Cu1 121.5(3) . . ? C1 N1 C5 118.0(3) . . ? C1 N1 Cu1 120.1(3) . . ? C5 N1 Cu1 121.5(3) . . ? N1 C1 C2 123.5(4) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 118.7(4) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 118.7(4) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C3 C4 C5 120.4(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? N1 C5 C4 120.7(4) . . ? N1 C5 C6 118.3(3) . . ? C4 C5 C6 121.0(4) . . ? C5 C6 C7 113.2(3) . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? C7 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? O1 C7 C6 110.8(3) . . ? O1 C7 H7A 109.5 . . ? C6 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? O3 C8 O2 121.8(2) . 2_655 ? O3 C8 O2 121.8(2) . . ? O2 C8 O2 116.3(5) 2_655 . ? H333 O111 H444 90(6) . . ? H111 O222 H222 118(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 O1 C7 175.0(4) 5_655 . . . ? O2 Cu1 O1 C7 -177.0(6) . . . . ? N1 Cu1 O1 C7 -9.6(3) . . . . ? O1 Cu1 O1 Cu1 0.0 5_655 . . 5_655 ? O2 Cu1 O1 Cu1 8.0(8) . . . 5_655 ? N1 Cu1 O1 Cu1 175.38(15) . . . 5_655 ? O1 Cu1 O2 C8 78.5(7) . . . . ? O1 Cu1 O2 C8 86.3(2) 5_655 . . . ? N1 Cu1 O2 C8 -88.8(2) . . . . ? O1 Cu1 N1 C1 -152.6(3) . . . . ? O1 Cu1 N1 C1 -132.0(6) 5_655 . . . ? O2 Cu1 N1 C1 25.1(3) . . . . ? O1 Cu1 N1 C5 34.2(3) . . . . ? O1 Cu1 N1 C5 54.9(7) 5_655 . . . ? O2 Cu1 N1 C5 -148.0(3) . . . . ? C5 N1 C1 C2 2.2(6) . . . . ? Cu1 N1 C1 C2 -171.2(3) . . . . ? N1 C1 C2 C3 -0.5(6) . . . . ? C1 C2 C3 C4 -0.9(6) . . . . ? C2 C3 C4 C5 0.6(6) . . . . ? C1 N1 C5 C4 -2.4(6) . . . . ? Cu1 N1 C5 C4 170.8(3) . . . . ? C1 N1 C5 C6 177.3(4) . . . . ? Cu1 N1 C5 C6 -9.5(5) . . . . ? C3 C4 C5 N1 1.1(6) . . . . ? C3 C4 C5 C6 -178.6(4) . . . . ? N1 C5 C6 C7 -47.4(5) . . . . ? C4 C5 C6 C7 132.3(4) . . . . ? Cu1 O1 C7 C6 -35.8(5) . . . . ? Cu1 O1 C7 C6 137.7(3) 5_655 . . . ? C5 C6 C7 O1 71.9(4) . . . . ? Cu1 O2 C8 O3 6.6(2) . . . . ? Cu1 O2 C8 O2 -173.4(2) . . . 2_655 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.615 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.113 # Attachment '- 2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 818782' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 Cu N O4' _chemical_formula_weight 336.82 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.794(5) _cell_length_b 24.697(5) _cell_length_c 11.500(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 93.631(5) _cell_angle_gamma 90.000(5) _cell_volume 1358.8(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6296 _cell_measurement_theta_min 3.2963 _cell_measurement_theta_max 32.5863 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.646 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 1.622 _exptl_absorpt_correction_T_min 0.7066 _exptl_absorpt_correction_T_max 0.8047 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4222 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0539 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4222 _reflns_number_gt 3460 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0333P)^2^+2.9101P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4222 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.00185(10) -0.01434(2) 0.62705(4) 0.01238(15) Uani 1 1 d . . . O1 O 0.0242(6) 0.04784(11) 0.5249(2) 0.0149(6) Uani 1 1 d . . . O2 O -0.1166(5) -0.07890(11) 0.7147(2) 0.0134(6) Uani 1 1 d . . . O3 O 0.4641(6) -0.04247(11) 0.6721(2) 0.0170(6) Uani 1 1 d . . . O4 O 0.6647(6) -0.16789(11) 0.8161(2) 0.0168(6) Uani 1 1 d . . . N1 N 0.0100(7) 0.03438(13) 0.7658(3) 0.0131(7) Uani 1 1 d . . . C1 C 0.1680(9) 0.02229(18) 0.8626(3) 0.0228(10) Uani 1 1 d . . . H1 H 0.2758 -0.0100 0.8642 0.027 Uiso 1 1 calc R . . C2 C 0.1800(10) 0.0549(2) 0.9598(4) 0.0273(11) Uani 1 1 d . . . H2 H 0.2953 0.0454 1.0269 0.033 Uiso 1 1 calc R . . C3 C 0.0231(10) 0.10142(19) 0.9584(4) 0.0256(10) Uani 1 1 d . . . H3 H 0.0245 0.1242 1.0250 0.031 Uiso 1 1 calc R . . C4 C -0.1362(10) 0.11432(18) 0.8587(4) 0.0237(10) Uani 1 1 d . . . H4 H -0.2442 0.1466 0.8555 0.028 Uiso 1 1 calc R . . C5 C -0.1397(8) 0.08016(17) 0.7624(3) 0.0161(9) Uani 1 1 d . . . C6 C -0.2962(9) 0.09365(18) 0.6493(3) 0.0203(9) Uani 1 1 d . . . H6A H -0.3967 0.1284 0.6570 0.024 Uiso 1 1 calc R . . H6B H -0.4362 0.0651 0.6297 0.024 Uiso 1 1 calc R . . C7 C -0.0939(9) 0.09826(17) 0.5506(3) 0.0179(9) Uani 1 1 d . . . H7A H -0.1961 0.1127 0.4798 0.021 Uiso 1 1 calc R . . H7B H 0.0573 0.1241 0.5742 0.021 Uiso 1 1 calc R . . C8 C 0.6189(8) -0.07954(16) 0.7124(3) 0.0126(8) Uani 1 1 d . . . C9 C 0.4782(8) -0.12886(16) 0.7636(4) 0.0166(9) Uani 1 1 d . . . H9A H 0.3518 -0.1162 0.8228 0.020 Uiso 1 1 calc R . . H9B H 0.3616 -0.1468 0.7007 0.020 Uiso 1 1 calc R . . C10 C 0.8115(8) -0.20057(16) 0.7451(3) 0.0138(8) Uani 1 1 d . . . C11 C 0.9896(9) -0.23764(17) 0.8026(4) 0.0204(9) Uani 1 1 d . . . H11 H 0.9991 -0.2396 0.8853 0.024 Uiso 1 1 calc R . . C12 C 1.1519(9) -0.27150(18) 0.7406(4) 0.0238(10) Uani 1 1 d . . . H12 H 1.2735 -0.2966 0.7807 0.029 Uiso 1 1 calc R . . C13 C 1.1401(9) -0.26947(18) 0.6197(4) 0.0199(9) Uani 1 1 d . . . H13 H 1.2537 -0.2927 0.5769 0.024 Uiso 1 1 calc R . . C14 C 0.9608(9) -0.23313(17) 0.5632(3) 0.0202(10) Uani 1 1 d . . . H14 H 0.9492 -0.2317 0.4805 0.024 Uiso 1 1 calc R . . C15 C 0.7982(8) -0.19887(17) 0.6244(3) 0.0168(9) Uani 1 1 d . . . H15 H 0.6763 -0.1740 0.5839 0.020 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0142(3) 0.0107(3) 0.0123(2) 0.0003(2) 0.00104(17) 0.0002(3) O1 0.0196(15) 0.0114(16) 0.0139(14) 0.0001(11) 0.0019(12) 0.0004(12) O2 0.0087(14) 0.0135(15) 0.0178(14) 0.0022(11) 0.0004(11) 0.0009(12) O3 0.0106(14) 0.0126(15) 0.0274(15) 0.0041(12) -0.0014(12) 0.0032(12) O4 0.0177(15) 0.0157(16) 0.0169(14) 0.0029(11) -0.0009(12) -0.0003(13) N1 0.0121(17) 0.0142(18) 0.0132(16) 0.0009(13) 0.0016(13) -0.0026(14) C1 0.027(2) 0.023(3) 0.018(2) 0.0025(18) -0.0028(17) 0.002(2) C2 0.033(3) 0.032(3) 0.016(2) 0.0015(19) -0.002(2) -0.006(2) C3 0.034(3) 0.028(3) 0.015(2) -0.0056(19) 0.0051(19) -0.013(2) C4 0.032(3) 0.016(2) 0.025(2) -0.0055(18) 0.010(2) -0.001(2) C5 0.014(2) 0.017(2) 0.018(2) -0.0014(17) 0.0032(16) -0.0024(18) C6 0.021(2) 0.016(2) 0.023(2) -0.0035(17) -0.0015(18) 0.0074(19) C7 0.022(2) 0.013(2) 0.019(2) -0.0012(16) -0.0019(17) 0.0020(18) C8 0.011(2) 0.017(2) 0.0103(18) -0.0029(16) 0.0015(15) -0.0017(17) C9 0.013(2) 0.015(2) 0.023(2) 0.0036(17) 0.0013(16) 0.0016(17) C10 0.0107(19) 0.011(2) 0.020(2) 0.0007(16) 0.0005(16) -0.0071(17) C11 0.022(2) 0.019(2) 0.021(2) 0.0030(17) -0.0004(18) -0.0045(19) C12 0.022(2) 0.018(2) 0.031(2) 0.0050(19) 0.0002(19) 0.003(2) C13 0.016(2) 0.018(2) 0.026(2) -0.0036(17) 0.0040(18) -0.0026(19) C14 0.026(2) 0.020(2) 0.015(2) -0.0025(17) -0.0003(18) -0.0043(19) C15 0.016(2) 0.016(2) 0.018(2) 0.0014(17) -0.0008(17) -0.0019(18) _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 1.930(3) 3_556 ? Cu1 O1 1.940(3) . ? Cu1 O2 1.988(3) . ? Cu1 N1 1.997(3) . ? Cu1 O3 2.349(3) . ? Cu1 Cu1 3.0057(15) 3_556 ? O1 C7 1.407(5) . ? O1 Cu1 1.930(3) 3_556 ? O2 C8 1.267(5) 1_455 ? O3 C8 1.249(5) . ? O4 C10 1.373(5) . ? O4 C9 1.423(5) . ? N1 C5 1.338(5) . ? N1 C1 1.339(5) . ? C1 C2 1.377(6) . ? C1 H1 0.9500 . ? C2 C3 1.372(7) . ? C2 H2 0.9500 . ? C3 C4 1.375(6) . ? C3 H3 0.9500 . ? C4 C5 1.392(6) . ? C4 H4 0.9500 . ? C5 C6 1.497(5) . ? C6 C7 1.542(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O2 1.267(5) 1_655 ? C8 C9 1.528(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C15 1.386(5) . ? C10 C11 1.390(6) . ? C11 C12 1.373(6) . ? C11 H11 0.9500 . ? C12 C13 1.388(6) . ? C12 H12 0.9500 . ? C13 C14 1.377(6) . ? C13 H13 0.9500 . ? C14 C15 1.374(6) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 78.12(13) 3_556 . ? O1 Cu1 O2 96.37(11) 3_556 . ? O1 Cu1 O2 165.93(11) . . ? O1 Cu1 N1 168.11(12) 3_556 . ? O1 Cu1 N1 90.45(13) . . ? O2 Cu1 N1 94.01(12) . . ? O1 Cu1 O3 94.52(11) 3_556 . ? O1 Cu1 O3 106.27(11) . . ? O2 Cu1 O3 86.95(11) . . ? N1 Cu1 O3 91.81(12) . . ? O1 Cu1 Cu1 39.18(8) 3_556 3_556 ? O1 Cu1 Cu1 38.94(8) . 3_556 ? O2 Cu1 Cu1 134.22(8) . 3_556 ? N1 Cu1 Cu1 129.31(10) . 3_556 ? O3 Cu1 Cu1 103.38(7) . 3_556 ? C7 O1 Cu1 124.5(2) . 3_556 ? C7 O1 Cu1 122.3(2) . . ? Cu1 O1 Cu1 101.88(13) 3_556 . ? C8 O2 Cu1 108.5(3) 1_455 . ? C8 O3 Cu1 146.0(3) . . ? C10 O4 C9 118.5(3) . . ? C5 N1 C1 119.2(3) . . ? C5 N1 Cu1 120.1(3) . . ? C1 N1 Cu1 120.7(3) . . ? N1 C1 C2 122.4(4) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C3 C2 C1 119.1(4) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 118.6(4) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C3 C4 C5 120.1(4) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? N1 C5 C4 120.6(4) . . ? N1 C5 C6 116.9(3) . . ? C4 C5 C6 122.5(4) . . ? C5 C6 C7 110.6(3) . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C7 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? O1 C7 C6 111.7(3) . . ? O1 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? O1 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? O3 C8 O2 124.7(4) . 1_655 ? O3 C8 C9 117.5(3) . . ? O2 C8 C9 117.9(3) 1_655 . ? O4 C9 C8 115.0(3) . . ? O4 C9 H9A 108.5 . . ? C8 C9 H9A 108.5 . . ? O4 C9 H9B 108.5 . . ? C8 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? O4 C10 C15 125.8(4) . . ? O4 C10 C11 115.3(3) . . ? C15 C10 C11 118.9(4) . . ? C12 C11 C10 120.3(4) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 120.7(4) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C14 C13 C12 118.7(4) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C15 C14 C13 121.1(4) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C10 120.2(4) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? 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 O1 Cu1 O1 C7 144.8(3) 3_556 . . . ? O2 Cu1 O1 C7 76.7(5) . . . . ? N1 Cu1 O1 C7 -31.9(3) . . . . ? O3 Cu1 O1 C7 -123.9(3) . . . . ? Cu1 Cu1 O1 C7 144.8(3) 3_556 . . . ? O1 Cu1 O1 Cu1 0.0 3_556 . . 3_556 ? O2 Cu1 O1 Cu1 -68.1(5) . . . 3_556 ? N1 Cu1 O1 Cu1 -176.69(13) . . . 3_556 ? O3 Cu1 O1 Cu1 91.29(13) . . . 3_556 ? O1 Cu1 O2 C8 -86.0(3) 3_556 . . 1_455 ? O1 Cu1 O2 C8 -20.0(6) . . . 1_455 ? N1 Cu1 O2 C8 88.2(3) . . . 1_455 ? O3 Cu1 O2 C8 179.8(2) . . . 1_455 ? Cu1 Cu1 O2 C8 -74.4(3) 3_556 . . 1_455 ? O1 Cu1 O3 C8 -85.8(5) 3_556 . . . ? O1 Cu1 O3 C8 -164.8(4) . . . . ? O2 Cu1 O3 C8 10.3(5) . . . . ? N1 Cu1 O3 C8 104.3(5) . . . . ? Cu1 Cu1 O3 C8 -124.5(4) 3_556 . . . ? O1 Cu1 N1 C5 26.4(8) 3_556 . . . ? O1 Cu1 N1 C5 42.2(3) . . . . ? O2 Cu1 N1 C5 -124.4(3) . . . . ? O3 Cu1 N1 C5 148.5(3) . . . . ? Cu1 Cu1 N1 C5 39.6(3) 3_556 . . . ? O1 Cu1 N1 C1 -152.6(5) 3_556 . . . ? O1 Cu1 N1 C1 -136.7(3) . . . . ? O2 Cu1 N1 C1 56.7(3) . . . . ? O3 Cu1 N1 C1 -30.4(3) . . . . ? Cu1 Cu1 N1 C1 -139.4(3) 3_556 . . . ? C5 N1 C1 C2 0.8(6) . . . . ? Cu1 N1 C1 C2 179.7(3) . . . . ? N1 C1 C2 C3 0.5(7) . . . . ? C1 C2 C3 C4 -1.4(7) . . . . ? C2 C3 C4 C5 1.0(7) . . . . ? C1 N1 C5 C4 -1.3(6) . . . . ? Cu1 N1 C5 C4 179.8(3) . . . . ? C1 N1 C5 C6 175.7(4) . . . . ? Cu1 N1 C5 C6 -3.2(5) . . . . ? C3 C4 C5 N1 0.4(6) . . . . ? C3 C4 C5 C6 -176.4(4) . . . . ? N1 C5 C6 C7 -58.5(5) . . . . ? C4 C5 C6 C7 118.4(4) . . . . ? Cu1 O1 C7 C6 123.0(3) 3_556 . . . ? Cu1 O1 C7 C6 -13.9(4) . . . . ? C5 C6 C7 O1 67.7(4) . . . . ? Cu1 O3 C8 O2 175.2(3) . . . 1_655 ? Cu1 O3 C8 C9 -5.4(6) . . . . ? C10 O4 C9 C8 -74.1(4) . . . . ? O3 C8 C9 O4 -175.5(3) . . . . ? O2 C8 C9 O4 4.0(5) 1_655 . . . ? C9 O4 C10 C15 0.8(5) . . . . ? C9 O4 C10 C11 179.9(3) . . . . ? O4 C10 C11 C12 -178.4(4) . . . . ? C15 C10 C11 C12 0.8(6) . . . . ? C10 C11 C12 C13 -0.3(6) . . . . ? C11 C12 C13 C14 -0.5(7) . . . . ? C12 C13 C14 C15 0.8(6) . . . . ? C13 C14 C15 C10 -0.3(6) . . . . ? O4 C10 C15 C14 178.6(4) . . . . ? C11 C10 C15 C14 -0.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.425 _refine_diff_density_min -0.711 _refine_diff_density_rms 0.097