Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name 'Prof. Yaoyu Wang' _publ_contact_author_email wyaoyu@nwu.edu.cn _publ_section_title ; Hydro(solvo)thermal synthesis, structures, luminescence of 2D zinc(II) and 1D copper(II) complexes constructed from pyridine-2,6-dicarboxylic acid N-oxide and decarboxylation of the ligand ; loop_ _publ_author_name 'Wang Yaoyu' 'Jian-Qiang Liu' 'Shie-Ming Peng' 'Qi-Zheng Shi' ; Weiping Wu ; 'Ya-Pan Wu' 'Xi-Rui Zeng' # Attachment 'B701384A_ccdc_631999_632000_cif.txt' data_xb0953m _database_code_depnum_ccdc_archive 'CCDC 631999' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H5 N O6 Zn' _chemical_formula_weight 264.49 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.8976(5) _cell_length_b 5.8184(5) _cell_length_c 23.7875(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.5730(10) _cell_angle_gamma 90.00 _cell_volume 816.22(12) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 865 _cell_measurement_theta_min 3.61 _cell_measurement_theta_max 24.73 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.152 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 3.018 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4480 _exptl_absorpt_correction_T_max 0.8280 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4663 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.17 _reflns_number_total 1806 _reflns_number_gt 1323 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement APEX2 _computing_data_reduction APEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics APEX2 _computing_publication_material APEX2 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The water H atoms were located in a different Fourier map and refined with restrained O-H bond lengths(0.85(2)\%A) and fixed isotropic displacement parameters(0.080\%A). ; _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^)+(0.0522P)^2^] 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 1806 _refine_ls_number_parameters 142 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0958 _refine_ls_wR_factor_gt 0.0910 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.037 _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 Zn1 Zn 0.25523(7) 0.91826(7) 0.034043(17) 0.02136(16) Uani 1 1 d . . . N1 N 0.3646(5) 0.5429(5) 0.10981(11) 0.0167(6) Uani 1 1 d . . . O1 O 0.3777(5) 0.6307(4) 0.05759(10) 0.0248(6) Uani 1 1 d . . . O2 O 0.1044(5) 0.9688(4) 0.10265(10) 0.0265(6) Uani 1 1 d . . . O3 O -0.0914(6) 0.8433(6) 0.17513(13) 0.0472(9) Uani 1 1 d . . . O4 O 0.8381(4) 0.4266(4) 0.06812(11) 0.0229(6) Uani 1 1 d . . . O5 O 0.6086(4) 0.1399(4) 0.04057(10) 0.0185(5) Uani 1 1 d . . . O6 O 0.1296(5) 1.2080(4) 0.00556(10) 0.0219(6) Uani 1 1 d D . . C1 C 0.0609(7) 0.8256(7) 0.14137(15) 0.0247(9) Uani 1 1 d . . . C2 C 0.2152(6) 0.6154(6) 0.14900(14) 0.0190(8) Uani 1 1 d . . . C3 C 0.2118(7) 0.4995(7) 0.19996(15) 0.0260(9) Uani 1 1 d . . . H3 H 0.1109 0.5459 0.2275 0.031 Uiso 1 1 calc R . . C4 C 0.3555(7) 0.3159(7) 0.21069(15) 0.0282(9) Uani 1 1 d . . . H4 H 0.3502 0.2383 0.2448 0.034 Uiso 1 1 calc R . . C5 C 0.5069(7) 0.2503(6) 0.16966(15) 0.0254(9) Uani 1 1 d . . . H5 H 0.6082 0.1307 0.1764 0.030 Uiso 1 1 calc R . . C6 C 0.5070(6) 0.3632(6) 0.11877(14) 0.0161(7) Uani 1 1 d . . . C7 C 0.6659(6) 0.3081(6) 0.07179(14) 0.0171(8) Uani 1 1 d . . . H6A H 0.064(9) 1.287(8) 0.0303(17) 0.080 Uiso 1 1 d D . . H6B H 0.202(8) 1.293(8) -0.0168(19) 0.080 Uiso 1 1 d 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 Zn1 0.0246(3) 0.0202(2) 0.0194(2) 0.00082(18) 0.00523(17) 0.00550(19) N1 0.0207(16) 0.0170(15) 0.0125(14) 0.0013(12) 0.0031(12) 0.0038(12) O1 0.0364(16) 0.0272(13) 0.0110(12) 0.0066(10) 0.0099(11) 0.0158(12) O2 0.0341(16) 0.0259(14) 0.0196(13) 0.0026(11) 0.0102(12) 0.0132(12) O3 0.053(2) 0.0507(19) 0.0389(18) 0.0169(16) 0.0318(16) 0.0331(17) O4 0.0214(14) 0.0218(13) 0.0256(13) -0.0015(11) 0.0081(11) 0.0002(11) O5 0.0194(13) 0.0183(12) 0.0179(13) -0.0039(10) 0.0033(11) 0.0025(10) O6 0.0248(15) 0.0170(13) 0.0241(14) 0.0042(11) 0.0089(12) 0.0038(11) C1 0.033(2) 0.026(2) 0.0153(18) -0.0029(16) 0.0030(17) 0.0126(17) C2 0.0204(19) 0.0238(19) 0.0128(17) -0.0006(15) 0.0075(14) 0.0051(15) C3 0.030(2) 0.032(2) 0.0162(18) 0.0023(16) 0.0068(17) 0.0095(18) C4 0.037(2) 0.031(2) 0.0177(19) 0.0058(17) 0.0073(18) 0.0092(18) C5 0.031(2) 0.026(2) 0.0195(18) 0.0039(17) 0.0030(17) 0.0095(18) C6 0.0152(18) 0.0178(17) 0.0153(17) -0.0010(14) 0.0027(14) -0.0009(14) C7 0.020(2) 0.0137(16) 0.0180(18) 0.0066(15) 0.0010(15) 0.0065(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 Zn1 O2 1.889(2) . ? Zn1 O1 1.904(2) . ? Zn1 O6 1.960(2) . ? Zn1 O5 1.984(2) 3_665 ? Zn1 O5 2.454(2) 1_565 ? N1 O1 1.346(3) . ? N1 C6 1.357(4) . ? N1 C2 1.357(4) . ? O2 C1 1.270(5) . ? O3 C1 1.215(5) . ? O4 C7 1.231(4) . ? O5 C7 1.272(4) . ? O5 Zn1 1.984(2) 3_665 ? O5 Zn1 2.454(2) 1_545 ? O6 H6A 0.843(10) . ? O6 H6B 0.842(10) . ? C1 C2 1.534(5) . ? C2 C3 1.388(5) . ? C3 C4 1.385(5) . ? C3 H3 0.9300 . ? C4 C5 1.383(5) . ? C4 H4 0.9300 . ? C5 C6 1.377(5) . ? C5 H5 0.9300 . ? C6 C7 1.500(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 O2 Zn1 O1 93.62(11) . . ? O2 Zn1 O6 89.14(11) . . ? O1 Zn1 O6 176.86(10) . . ? O2 Zn1 O5 175.76(11) . 3_665 ? O1 Zn1 O5 87.57(10) . 3_665 ? O6 Zn1 O5 89.57(10) . 3_665 ? O2 Zn1 O5 105.68(10) . 1_565 ? O1 Zn1 O5 97.11(10) . 1_565 ? O6 Zn1 O5 83.55(10) . 1_565 ? O5 Zn1 O5 78.18(9) 3_665 1_565 ? O1 N1 C6 113.4(3) . . ? O1 N1 C2 124.0(3) . . ? C6 N1 C2 122.5(3) . . ? N1 O1 Zn1 125.4(2) . . ? C1 O2 Zn1 128.6(2) . . ? C7 O5 Zn1 123.1(2) . 3_665 ? C7 O5 Zn1 131.4(2) . 1_545 ? Zn1 O5 Zn1 101.82(9) 3_665 1_545 ? Zn1 O6 H6A 114(4) . . ? Zn1 O6 H6B 122(4) . . ? H6A O6 H6B 111(5) . . ? O3 C1 O2 125.4(4) . . ? O3 C1 C2 115.5(3) . . ? O2 C1 C2 119.0(3) . . ? N1 C2 C3 117.6(3) . . ? N1 C2 C1 123.7(3) . . ? C3 C2 C1 118.5(3) . . ? C4 C3 C2 121.5(3) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C5 C4 C3 118.7(3) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C6 C5 C4 119.6(3) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? N1 C6 C5 120.0(3) . . ? N1 C6 C7 116.0(3) . . ? C5 C6 C7 124.0(3) . . ? O4 C7 O5 127.1(3) . . ? O4 C7 C6 117.1(3) . . ? O5 C7 C6 115.8(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 C6 N1 O1 Zn1 -166.0(2) . . . . ? C2 N1 O1 Zn1 17.8(5) . . . . ? O2 Zn1 O1 N1 -7.4(3) . . . . ? O6 Zn1 O1 N1 -159.1(19) . . . . ? O5 Zn1 O1 N1 176.7(3) 3_665 . . . ? O5 Zn1 O1 N1 99.0(3) 1_565 . . . ? O1 Zn1 O2 C1 -15.7(3) . . . . ? O6 Zn1 O2 C1 162.8(3) . . . . ? O5 Zn1 O2 C1 90.5(15) 3_665 . . . ? O5 Zn1 O2 C1 -114.1(3) 1_565 . . . ? Zn1 O2 C1 O3 -155.6(3) . . . . ? Zn1 O2 C1 C2 27.0(5) . . . . ? O1 N1 C2 C3 176.2(3) . . . . ? C6 N1 C2 C3 0.3(5) . . . . ? O1 N1 C2 C1 -7.5(6) . . . . ? C6 N1 C2 C1 176.7(3) . . . . ? O3 C1 C2 N1 166.9(4) . . . . ? O2 C1 C2 N1 -15.5(6) . . . . ? O3 C1 C2 C3 -16.9(6) . . . . ? O2 C1 C2 C3 160.8(4) . . . . ? N1 C2 C3 C4 0.0(6) . . . . ? C1 C2 C3 C4 -176.5(4) . . . . ? C2 C3 C4 C5 0.9(6) . . . . ? C3 C4 C5 C6 -2.0(6) . . . . ? O1 N1 C6 C5 -177.8(3) . . . . ? C2 N1 C6 C5 -1.5(5) . . . . ? O1 N1 C6 C7 5.2(4) . . . . ? C2 N1 C6 C7 -178.5(3) . . . . ? C4 C5 C6 N1 2.3(6) . . . . ? C4 C5 C6 C7 179.1(4) . . . . ? Zn1 O5 C7 O4 -17.0(5) 3_665 . . . ? Zn1 O5 C7 O4 -171.2(2) 1_545 . . . ? Zn1 O5 C7 C6 164.4(2) 3_665 . . . ? Zn1 O5 C7 C6 10.2(4) 1_545 . . . ? N1 C6 C7 O4 80.5(4) . . . . ? C5 C6 C7 O4 -96.4(4) . . . . ? N1 C6 C7 O5 -100.7(4) . . . . ? C5 C6 C7 O5 82.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.17 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.527 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.109 data_j _database_code_depnum_ccdc_archive 'CCDC 632000' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 Cu N2 O6' _chemical_formula_sum 'C12 H8 Cu N2 O6' _chemical_formula_weight 339.74 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.3900(7) _cell_length_b 12.590(3) _cell_length_c 12.170(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.18(3) _cell_angle_gamma 90.00 _cell_volume 518.04(18) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2617 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 28.21 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 342 _exptl_absorpt_coefficient_mu 2.145 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6497 _exptl_absorpt_correction_T_max 0.7391 _exptl_absorpt_process_details 'SADABS(Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3157 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0153 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 25.17 _reflns_number_total 915 _reflns_number_gt 839 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+0.2458P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 915 _refine_ls_number_parameters 97 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0257 _refine_ls_R_factor_gt 0.0238 _refine_ls_wR_factor_ref 0.0738 _refine_ls_wR_factor_gt 0.0730 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 O3 O -0.0710(5) 0.46547(14) 0.84834(13) 0.0289(4) Uani 1 1 d . . . Cu1 Cu 0.0000 0.5000 1.0000 0.02330(18) Uani 1 2 d S . . O2 O 0.3688(5) 0.39065(13) 1.02473(13) 0.0301(4) Uani 1 1 d . . . C5 C 0.2634(6) 0.29944(17) 0.85322(18) 0.0214(5) Uani 1 1 d . . . N2 N 0.3897(5) 0.30376(14) 0.96110(15) 0.0208(4) Uani 1 1 d . . . O6 O 0.0596(5) 0.38859(14) 0.69307(13) 0.0330(4) Uani 1 1 d . . . C6 C 0.0734(6) 0.39284(17) 0.79352(18) 0.0229(5) Uani 1 1 d . . . C1 C 0.3090(7) 0.20524(18) 0.7971(2) 0.0279(5) Uani 1 1 d . . . H1A H 0.2202 0.2010 0.7232 0.033 Uiso 1 1 calc R . . C3 C 0.6109(7) 0.12779(18) 0.9554(2) 0.0313(6) Uani 1 1 d . . . H3B H 0.7345 0.0703 0.9914 0.038 Uiso 1 1 calc R . . C4 C 0.5626(6) 0.2204(2) 1.01154(19) 0.0251(5) Uani 1 1 d . . . H4A H 0.6512 0.2252 1.0855 0.030 Uiso 1 1 calc R . . C2 C 0.4801(7) 0.11881(19) 0.8473(2) 0.0321(6) Uani 1 1 d . . . H2A H 0.5072 0.0555 0.8092 0.039 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 O3 0.0325(9) 0.0307(9) 0.0225(8) -0.0035(7) -0.0047(7) 0.0106(8) Cu1 0.0281(3) 0.0209(3) 0.0202(3) -0.00260(13) -0.00324(17) 0.00609(14) O2 0.0368(10) 0.0257(9) 0.0263(8) -0.0093(7) -0.0087(7) 0.0106(7) C5 0.0176(11) 0.0230(11) 0.0239(11) -0.0011(9) 0.0027(9) -0.0037(8) N2 0.0184(9) 0.0200(9) 0.0242(9) -0.0027(7) 0.0031(7) 0.0001(7) O6 0.0398(10) 0.0386(10) 0.0201(9) -0.0022(7) -0.0010(7) 0.0037(8) C6 0.0207(11) 0.0244(11) 0.0232(11) -0.0019(9) -0.0017(9) -0.0043(9) C1 0.0209(12) 0.0315(13) 0.0315(12) -0.0072(10) 0.0036(9) -0.0037(9) C3 0.0227(13) 0.0231(12) 0.0485(16) 0.0037(11) 0.0051(11) 0.0013(9) C4 0.0212(11) 0.0250(13) 0.0290(12) 0.0047(9) 0.0015(9) 0.0020(9) C2 0.0252(13) 0.0232(12) 0.0487(15) -0.0093(11) 0.0069(11) -0.0009(9) _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 O3 C6 1.252(3) . ? O3 Cu1 1.8944(16) . ? Cu1 O2 1.8692(16) . ? Cu1 O2 1.8692(16) 3_567 ? Cu1 O3 1.8944(16) 3_567 ? O2 N2 1.345(2) . ? C5 N2 1.352(3) . ? C5 C1 1.383(3) . ? C5 C6 1.502(3) . ? N2 C4 1.330(3) . ? O6 C6 1.221(3) . ? C1 C2 1.357(4) . ? C1 H1A 0.9300 . ? C3 C2 1.361(4) . ? C3 C4 1.368(3) . ? C3 H3B 0.9300 . ? C4 H4A 0.9300 . ? C2 H2A 0.9300 . ? 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 C6 O3 Cu1 131.28(15) . . ? O2 Cu1 O2 180.00 . 3_567 ? O2 Cu1 O3 91.36(7) . . ? O2 Cu1 O3 88.64(7) 3_567 . ? O2 Cu1 O3 88.64(7) . 3_567 ? O2 Cu1 O3 91.36(7) 3_567 3_567 ? O3 Cu1 O3 180.00 . 3_567 ? N2 O2 Cu1 124.68(13) . . ? N2 C5 C1 118.4(2) . . ? N2 C5 C6 122.17(19) . . ? C1 C5 C6 119.5(2) . . ? C4 N2 O2 114.57(18) . . ? C4 N2 C5 120.9(2) . . ? O2 N2 C5 124.44(18) . . ? O6 C6 O3 125.3(2) . . ? O6 C6 C5 115.7(2) . . ? O3 C6 C5 118.96(19) . . ? C2 C1 C5 121.7(2) . . ? C2 C1 H1A 119.2 . . ? C5 C1 H1A 119.2 . . ? C2 C3 C4 120.7(2) . . ? C2 C3 H3B 119.6 . . ? C4 C3 H3B 119.6 . . ? N2 C4 C3 120.5(2) . . ? N2 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? C1 C2 C3 117.8(2) . . ? C1 C2 H2A 121.1 . . ? C3 C2 H2A 121.1 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.17 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.270 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.065