# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name 'Can-Zhong Lu' _publ_contact_author_address ; State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, the Chinese Academy of Sciences, Fuzhou, Fujian 350002, P. R. China ; _publ_contact_author_email czlu@fjirsm.ac.cn loop_ _publ_author_name 'Zhen-Lan Fang' 'Rong-Ming Yu' 'Jie Zhang' 'Can-Zhong Lu' #=================================END data_2 _database_code_depnum_ccdc_archive 'CCDC 762252' #TrackingRef '1-6.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H8 Cu2 N3 O2' _chemical_formula_sum 'C14 H8 Cu2 N3 O2' _chemical_formula_weight 377.33 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 29.394(16) _cell_length_b 5.317(2) _cell_length_c 18.588(10) _cell_angle_alpha 90.00 _cell_angle_beta 118.972(7) _cell_angle_gamma 90.00 _cell_volume 2542(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2488 _cell_measurement_theta_min 2.4493 _cell_measurement_theta_max 27.4719 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.0700 _exptl_crystal_size_mid 0.0600 _exptl_crystal_size_min 0.0300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.972 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_absorpt_coefficient_mu 3.352 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8789 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Saturn70 _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7650 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 27.47 _diffrn_reflns_theta_min 2.4493 _diffrn_reflns_theta_max 27.4719 _reflns_number_total 2907 _reflns_number_gt 1914 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0664P)^2^+4.1782P] 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 conster _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2233 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1276 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.011 _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 Cu1 Cu 0.24580(2) 0.02119(12) 0.27890(4) 0.0324(2) Uani 1 1 d . . . Cu2 Cu 0.03173(2) -0.25598(10) 0.03685(4) 0.0276(2) Uani 1 1 d . . . C5 C 0.07947(18) -0.6565(9) -0.0142(3) 0.0238(11) Uani 1 1 d . . . C14 C 0.13239(17) -0.0711(9) 0.1681(3) 0.0216(10) Uani 1 1 d . . . C7 C 0.14200(17) -0.3890(10) 0.1035(3) 0.0261(11) Uani 1 1 d . . . C11 C 0.10909(17) 0.1254(9) 0.1931(3) 0.0243(11) Uani 1 1 d . . . C6 C 0.0727(2) -0.8378(10) -0.0740(3) 0.0315(12) Uani 1 1 d . . . H6A H 0.0392 -0.8810 -0.1139 0.038 Uiso 1 1 calc R . . C12 C 0.05499(18) 0.1687(9) 0.1505(3) 0.0228(10) Uani 1 1 d . . . C3 C 0.1725(2) -0.7051(12) 0.0388(4) 0.0446(15) Uani 1 1 d . . . H3A H 0.2063 -0.6575 0.0757 0.053 Uiso 1 1 calc R . . C4 C 0.13111(18) -0.5859(9) 0.0425(3) 0.0257(11) Uani 1 1 d . . . C13 C 0.03507(19) 0.3511(10) 0.1823(3) 0.0305(12) Uani 1 1 d . . . H13A H -0.0007 0.3752 0.1571 0.037 Uiso 1 1 calc R . . C9 C 0.1198(2) 0.4586(10) 0.2891(3) 0.0386(14) Uani 1 1 d . . . H9A H 0.1415 0.5590 0.3337 0.046 Uiso 1 1 calc R . . C10 C 0.1403(2) 0.2728(10) 0.2624(3) 0.0339(13) Uani 1 1 d . . . H10A H 0.1759 0.2435 0.2909 0.041 Uiso 1 1 calc R . . C2 C 0.1644(2) -0.8908(13) -0.0179(4) 0.0494(16) Uani 1 1 d . . . H2A H 0.1924 -0.9733 -0.0176 0.059 Uiso 1 1 calc R . . C8 C 0.0667(2) 0.4950(10) 0.2492(3) 0.0349(13) Uani 1 1 d . . . H8A H 0.0523 0.6176 0.2678 0.042 Uiso 1 1 calc R . . C1 C 0.1142(2) -0.9518(11) -0.0750(4) 0.0407(14) Uani 1 1 d . . . H1A H 0.1083 -1.0723 -0.1149 0.049 Uiso 1 1 calc R . . N2 N 0.18353(14) -0.1263(8) 0.2046(2) 0.0274(10) Uani 1 1 d . . . N1 N 0.18937(15) -0.3307(8) 0.1638(3) 0.0277(10) Uani 1 1 d . . . N4 N 0.10658(14) -0.2333(7) 0.1051(2) 0.0226(9) Uani 1 1 d . . . O2 O 0.03754(12) -0.5612(6) -0.0135(2) 0.0279(8) Uani 1 1 d . . . O1 O 0.02193(12) 0.0493(6) 0.0814(2) 0.0291(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0128(3) 0.0369(4) 0.0332(4) -0.0029(3) -0.0003(3) -0.0056(3) Cu2 0.0128(3) 0.0230(4) 0.0334(4) -0.0093(3) 0.0005(3) 0.0010(2) C5 0.021(2) 0.020(2) 0.028(3) 0.005(2) 0.011(2) 0.002(2) C14 0.012(2) 0.025(3) 0.020(2) 0.004(2) 0.0011(19) -0.0050(19) C7 0.013(2) 0.032(3) 0.029(3) 0.008(2) 0.007(2) 0.005(2) C11 0.016(2) 0.027(3) 0.024(2) 0.001(2) 0.005(2) -0.003(2) C6 0.032(3) 0.031(3) 0.032(3) -0.006(2) 0.016(2) -0.004(2) C12 0.021(2) 0.019(2) 0.024(2) -0.001(2) 0.007(2) -0.004(2) C3 0.025(3) 0.060(4) 0.040(3) -0.010(3) 0.008(3) 0.009(3) C4 0.021(2) 0.028(3) 0.024(2) 0.003(2) 0.008(2) 0.004(2) C13 0.024(3) 0.034(3) 0.028(3) -0.003(2) 0.008(2) 0.002(2) C9 0.045(3) 0.038(3) 0.028(3) -0.013(2) 0.013(3) -0.009(3) C10 0.024(3) 0.040(3) 0.029(3) -0.005(2) 0.005(2) -0.009(2) C2 0.039(3) 0.056(4) 0.058(4) -0.004(3) 0.027(3) 0.016(3) C8 0.039(3) 0.036(3) 0.032(3) -0.007(2) 0.019(3) 0.000(2) C1 0.048(4) 0.037(3) 0.043(3) -0.005(3) 0.027(3) 0.005(3) N2 0.0122(19) 0.032(2) 0.024(2) -0.0033(19) -0.0022(17) -0.0046(18) N1 0.0142(19) 0.028(2) 0.033(2) 0.0002(19) 0.0051(18) -0.0005(18) N4 0.013(2) 0.025(2) 0.0210(19) -0.0006(17) 0.0008(17) -0.0038(16) O2 0.0166(16) 0.0250(18) 0.0349(19) -0.0078(16) 0.0068(15) -0.0007(14) O1 0.0173(17) 0.0247(18) 0.0317(19) -0.0052(15) 0.0011(15) 0.0035(14) _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 N1 1.849(4) 4 ? Cu1 N2 1.850(4) . ? Cu1 Cu1 2.9225(13) 4 ? Cu1 Cu1 2.9225(13) 4_545 ? Cu2 O1 1.906(3) . ? Cu2 O2 1.922(3) . ? Cu2 N4 1.939(4) . ? Cu2 O2 2.103(3) 5_545 ? Cu2 O1 2.273(3) 5 ? C5 O2 1.339(6) . ? C5 C4 1.417(7) . ? C5 C6 1.411(7) . ? C14 N2 1.348(6) . ? C14 N4 1.352(6) . ? C14 C11 1.444(7) . ? C7 N1 1.334(6) . ? C7 N4 1.342(6) . ? C7 C4 1.460(7) . ? C11 C10 1.403(7) . ? C11 C12 1.410(6) . ? C6 C1 1.369(8) . ? C6 H6A 0.9300 . ? C12 O1 1.338(6) . ? C12 C13 1.403(7) . ? C3 C2 1.379(8) . ? C3 C4 1.402(7) . ? C3 H3A 0.9300 . ? C13 C8 1.370(7) . ? C13 H13A 0.9300 . ? C9 C10 1.370(8) . ? C9 C8 1.380(8) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C2 C1 1.375(8) . ? C2 H2A 0.9300 . ? C8 H8A 0.9300 . ? C1 H1A 0.9300 . ? N2 N1 1.383(6) . ? N1 Cu1 1.849(4) 4_545 ? O2 Cu2 2.103(3) 5_545 ? O1 Cu2 2.273(3) 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 N1 Cu1 N2 168.89(19) 4 . ? N1 Cu1 Cu1 64.99(13) 4 4 ? N2 Cu1 Cu1 109.91(14) . 4 ? N1 Cu1 Cu1 110.62(14) 4 4_545 ? N2 Cu1 Cu1 64.49(14) . 4_545 ? Cu1 Cu1 Cu1 130.94(6) 4 4_545 ? O1 Cu2 O2 176.58(14) . . ? O1 Cu2 N4 91.44(15) . . ? O2 Cu2 N4 91.78(15) . . ? O1 Cu2 O2 98.55(14) . 5_545 ? O2 Cu2 O2 79.30(15) . 5_545 ? N4 Cu2 O2 147.34(15) . 5_545 ? O1 Cu2 O1 80.08(15) . 5 ? O2 Cu2 O1 96.96(14) . 5 ? N4 Cu2 O1 129.70(15) . 5 ? O2 Cu2 O1 82.80(14) 5_545 5 ? O2 C5 C4 123.5(4) . . ? O2 C5 C6 119.2(4) . . ? C4 C5 C6 117.3(4) . . ? N2 C14 N4 108.6(4) . . ? N2 C14 C11 125.6(4) . . ? N4 C14 C11 125.8(4) . . ? N1 C7 N4 110.1(4) . . ? N1 C7 C4 124.5(4) . . ? N4 C7 C4 125.4(4) . . ? C10 C11 C12 118.8(5) . . ? C10 C11 C14 119.9(4) . . ? C12 C11 C14 121.3(4) . . ? C1 C6 C5 121.8(5) . . ? C1 C6 H6A 119.1 . . ? C5 C6 H6A 119.1 . . ? O1 C12 C13 118.4(4) . . ? O1 C12 C11 124.0(4) . . ? C13 C12 C11 117.6(4) . . ? C2 C3 C4 122.0(5) . . ? C2 C3 H3A 119.0 . . ? C4 C3 H3A 119.0 . . ? C3 C4 C5 119.0(5) . . ? C3 C4 C7 119.6(4) . . ? C5 C4 C7 121.4(4) . . ? C8 C13 C12 122.0(5) . . ? C8 C13 H13A 119.0 . . ? C12 C13 H13A 119.0 . . ? C10 C9 C8 119.2(5) . . ? C10 C9 H9A 120.4 . . ? C8 C9 H9A 120.4 . . ? C9 C10 C11 122.0(5) . . ? C9 C10 H10A 119.0 . . ? C11 C10 H10A 119.0 . . ? C1 C2 C3 118.8(5) . . ? C1 C2 H2A 120.6 . . ? C3 C2 H2A 120.6 . . ? C13 C8 C9 120.2(5) . . ? C13 C8 H8A 119.9 . . ? C9 C8 H8A 119.9 . . ? C6 C1 C2 121.0(5) . . ? C6 C1 H1A 119.5 . . ? C2 C1 H1A 119.5 . . ? C14 N2 N1 107.4(4) . . ? C14 N2 Cu1 137.9(4) . . ? N1 N2 Cu1 113.7(3) . . ? C7 N1 N2 106.7(4) . . ? C7 N1 Cu1 138.6(4) . 4_545 ? N2 N1 Cu1 112.7(3) . 4_545 ? C7 N4 C14 107.3(4) . . ? C7 N4 Cu2 126.4(3) . . ? C14 N4 Cu2 126.1(3) . . ? C5 O2 Cu2 128.6(3) . . ? C5 O2 Cu2 128.8(3) . 5_545 ? Cu2 O2 Cu2 100.70(15) . 5_545 ? C12 O1 Cu2 129.0(3) . . ? C12 O1 Cu2 122.7(3) . 5 ? Cu2 O1 Cu2 99.92(15) . 5 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.721 _refine_diff_density_min -1.010 _refine_diff_density_rms 0.382 #=================================END data_3 _database_code_depnum_ccdc_archive 'CCDC 762253' #TrackingRef '1-6.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 Cu2 N4 O5' _chemical_formula_sum 'C14 H14 Cu2 N4 O5' _chemical_formula_weight 445.39 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 20.435(3) _cell_length_b 4.9321(4) _cell_length_c 15.875(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.577(5) _cell_angle_gamma 90.00 _cell_volume 1541.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.1600 _exptl_crystal_size_mid 0.0800 _exptl_crystal_size_min 0.0500 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.919 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 2.795 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.764 _exptl_absorpt_correction_T_max 0.869 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Mercury70 _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5683 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 27.46 _reflns_number_total 1777 _reflns_number_gt 1419 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1007P)^2^+2.4442P] 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 conster _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1780 _refine_ls_number_parameters 124 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1672 _refine_ls_wR_factor_gt 0.1552 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.072 _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 0.46885(3) 0.26427(10) 0.59875(3) 0.0325(3) Uani 1 1 d . . . N2 N 0.40254(16) -0.0161(7) 0.5448(2) 0.0224(7) Uani 1 1 d . . . O2 O 0.45818(16) -0.5118(6) 0.35124(19) 0.0372(8) Uani 1 1 d . . . N1 N 0.48227(18) -0.1014(7) 0.4730(2) 0.0306(8) Uani 1 1 d . . . C7 C 0.4220(2) -0.1501(10) 0.4860(3) 0.0326(9) Uani 1 1 d . . . C6 C 0.3796(2) -0.3607(9) 0.4339(3) 0.0306(9) Uani 1 1 d . . . O3 O 0.4052(2) 0.4440(10) 0.6543(3) 0.0614(11) Uani 1 1 d D . . H3B H 0.417(4) 0.403(18) 0.7080(15) 0.092 Uiso 1 1 d D . . H3C H 0.3630(10) 0.412(18) 0.640(5) 0.092 Uiso 1 1 d D . . C5 C 0.3139(2) -0.3900(11) 0.4452(3) 0.0415(11) Uani 1 1 d . . . H5A H 0.3008 -0.2769 0.4847 0.050 Uiso 1 1 calc R . . C4 C 0.2687(3) -0.5784(12) 0.4005(3) 0.0510(13) Uani 1 1 d . . . H4A H 0.2258 -0.5931 0.4098 0.061 Uiso 1 1 calc R . . C3 C 0.2875(3) -0.7476(10) 0.3411(4) 0.0466(14) Uani 1 1 d . . . H3A H 0.2576 -0.8789 0.3109 0.056 Uiso 1 1 calc R . . C2 C 0.3515(3) -0.7186(10) 0.3271(3) 0.0403(12) Uani 1 1 d . . . H2A H 0.3633 -0.8312 0.2865 0.048 Uiso 1 1 calc R . . C1 C 0.3989(2) -0.5267(9) 0.3715(3) 0.0322(9) Uani 1 1 d . . . O4 O 0.5000 -0.0678(12) 0.7500 0.0607(16) Uani 1 2 d SD . . H1 H 0.509(3) -0.176(10) 0.714(3) 0.043(15) 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 Cu1 0.0348(4) 0.0335(4) 0.0317(4) -0.0080(2) 0.0133(3) -0.0046(2) N2 0.0208(16) 0.0282(17) 0.0208(15) -0.0078(13) 0.0103(12) -0.0045(12) O2 0.0408(19) 0.0389(19) 0.0350(17) -0.0090(14) 0.0156(14) -0.0107(14) N1 0.0294(19) 0.031(2) 0.0316(19) -0.0087(15) 0.0094(15) -0.0071(14) C7 0.032(2) 0.034(2) 0.031(2) 0.0022(19) 0.0081(18) 0.0002(18) C6 0.031(2) 0.033(2) 0.028(2) -0.0021(18) 0.0077(17) -0.0044(18) O3 0.054(3) 0.074(3) 0.059(2) -0.018(2) 0.021(2) -0.006(2) C5 0.037(3) 0.046(3) 0.042(3) -0.010(2) 0.012(2) -0.008(2) C4 0.039(3) 0.059(3) 0.054(3) -0.003(3) 0.012(2) -0.015(2) C3 0.048(3) 0.049(3) 0.038(3) -0.006(2) 0.003(2) -0.023(2) C2 0.051(3) 0.041(3) 0.028(2) -0.0047(19) 0.009(2) -0.008(2) C1 0.038(2) 0.031(2) 0.027(2) 0.0013(17) 0.0081(18) -0.0067(18) O4 0.077(4) 0.039(3) 0.058(4) 0.000 0.003(3) 0.000 _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 N1 1.885(3) 5_656 ? Cu1 O2 1.926(3) 5_656 ? Cu1 N2 1.965(3) . ? Cu1 O3 1.967(4) . ? N2 C7 1.290(5) . ? O2 C1 1.337(5) . ? O2 Cu1 1.926(3) 5_656 ? N1 C7 1.325(5) . ? N1 N1 1.388(7) 5_656 ? N1 Cu1 1.885(3) 5_656 ? C7 C6 1.459(7) . ? C6 C5 1.408(6) . ? C6 C1 1.420(6) . ? O3 H3B 0.846(7) . ? O3 H3C 0.845(7) . ? C5 C4 1.367(7) . ? C5 H5A 0.9300 . ? C4 C3 1.388(8) . ? C4 H4A 0.9300 . ? C3 C2 1.391(8) . ? C3 H3A 0.9300 . ? C2 C1 1.402(6) . ? C2 H2A 0.9300 . ? O4 H1 0.836(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 N1 Cu1 O2 92.41(14) 5_656 5_656 ? N1 Cu1 N2 81.48(13) 5_656 . ? O2 Cu1 N2 173.29(12) 5_656 . ? N1 Cu1 O3 169.87(17) 5_656 . ? O2 Cu1 O3 93.52(16) 5_656 . ? N2 Cu1 O3 92.93(16) . . ? C7 N2 Cu1 111.5(3) . . ? C1 O2 Cu1 126.0(3) . 5_656 ? C7 N1 N1 112.8(4) . 5_656 ? C7 N1 Cu1 133.1(3) . 5_656 ? N1 N1 Cu1 114.0(3) 5_656 5_656 ? N2 C7 N1 120.0(4) . . ? N2 C7 C6 121.6(4) . . ? N1 C7 C6 118.4(4) . . ? C5 C6 C1 118.8(4) . . ? C5 C6 C7 116.2(4) . . ? C1 C6 C7 124.9(4) . . ? Cu1 O3 H3B 108(6) . . ? Cu1 O3 H3C 123(6) . . ? H3B O3 H3C 103(7) . . ? C4 C5 C6 122.5(5) . . ? C4 C5 H5A 118.7 . . ? C6 C5 H5A 118.7 . . ? C5 C4 C3 119.4(5) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? C4 C3 C2 119.3(5) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C3 C2 C1 122.8(5) . . ? C3 C2 H2A 118.6 . . ? C1 C2 H2A 118.6 . . ? O2 C1 C2 117.7(4) . . ? O2 C1 C6 125.2(4) . . ? C2 C1 C6 117.2(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.967 _refine_diff_density_min -0.508 _refine_diff_density_rms 0.126