data_zhu88 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 Cu N6 O4' _chemical_formula_sum 'C6 H8 Cu N6 O4' _chemical_formula_weight 291.72 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 Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall -P2ac2ab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.6638(4) _cell_length_b 12.9337(7) _cell_length_c 18.6880(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2094.08(19) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 9936 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 29.02 _exptl_crystal_description Flat _exptl_crystal_colour blue _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.851 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 2.102 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6048 _exptl_absorpt_correction_T_max 0.8843 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21361 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0102 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2396 _reflns_number_gt 2228 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0284P)^2^+1.7287P] 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 2396 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0219 _refine_ls_R_factor_gt 0.0202 _refine_ls_wR_factor_ref 0.0552 _refine_ls_wR_factor_gt 0.0541 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 0.136890(19) 0.537011(13) 1.010409(10) 0.01731(7) Uani 1 1 d . . . C1 C -0.07620(17) 0.66391(11) 0.93541(8) 0.0221(3) Uani 1 1 d . . . C2 C -0.11898(19) 0.76002(12) 0.89304(9) 0.0272(3) Uani 1 1 d . . . H2A H -0.2326 0.7679 0.8938 0.033 Uiso 1 1 calc R . . H2B H -0.0874 0.7498 0.8426 0.033 Uiso 1 1 calc R . . C3 C 0.08291(17) 0.41729(11) 0.88385(8) 0.0218(3) Uani 1 1 d . . . C4 C 0.14315(18) 0.35986(13) 0.81881(9) 0.0284(3) Uani 1 1 d . . . H4A H 0.2107 0.3027 0.8349 0.034 Uiso 1 1 calc R . . H4B H 0.0549 0.3290 0.7928 0.034 Uiso 1 1 calc R . . C5 C 0.2325(2) 0.42825(15) 0.76821(9) 0.0335(4) Uani 1 1 d . . . H5A H 0.3125 0.4671 0.7949 0.040 Uiso 1 1 calc R . . H5B H 0.2845 0.3855 0.7315 0.040 Uiso 1 1 calc R . . C6 C 0.45350(18) 0.64069(12) 1.07957(8) 0.0251(3) Uani 1 1 d . . . H6A H 0.5636 0.6533 1.0684 0.030 Uiso 1 1 calc R . . H6B H 0.4484 0.5873 1.1174 0.030 Uiso 1 1 calc R . . N1 N 0.1471(3) 0.67912(16) 0.75245(14) 0.0667(6) Uani 1 1 d . . . N2 N 0.14266(19) 0.59269(13) 0.74601(9) 0.0379(4) Uani 1 1 d . . . N3 N 0.1241(2) 0.50122(14) 0.73355(10) 0.0443(4) Uani 1 1 d . . . N4 N 0.37366(14) 0.60227(11) 1.01445(7) 0.0230(3) Uani 1 1 d . . . N5 N 0.43097(15) 0.62698(10) 0.95605(7) 0.0250(3) Uani 1 1 d . . . N6 N 0.4717(2) 0.64226(14) 0.90003(9) 0.0431(4) Uani 1 1 d . . . O1 O 0.05627(12) 0.59478(9) 1.09966(6) 0.0283(2) Uani 1 1 d . . . O2 O 0.05810(13) 0.65977(9) 0.96038(7) 0.0306(3) Uani 1 1 d . . . O3 O 0.17923(13) 0.47110(9) 0.91760(7) 0.0317(3) Uani 1 1 d . . . O4 O 0.17656(14) 0.40545(9) 1.05885(7) 0.0338(3) 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 0.01371(10) 0.01716(10) 0.02107(11) -0.00354(6) -0.00041(6) 0.00038(6) C1 0.0255(7) 0.0204(7) 0.0204(7) -0.0035(5) 0.0002(6) 0.0049(6) C2 0.0351(8) 0.0242(7) 0.0225(7) 0.0012(6) -0.0018(6) 0.0071(6) C3 0.0221(7) 0.0212(7) 0.0220(7) -0.0036(5) 0.0009(6) 0.0016(6) C4 0.0278(8) 0.0305(8) 0.0271(8) -0.0103(6) 0.0048(6) -0.0010(6) C5 0.0314(8) 0.0407(9) 0.0283(8) -0.0054(7) 0.0043(7) -0.0043(7) C6 0.0254(7) 0.0226(7) 0.0274(8) 0.0053(6) -0.0092(6) -0.0032(6) N1 0.0893(16) 0.0434(10) 0.0674(14) -0.0088(10) -0.0306(12) -0.0025(11) N2 0.0442(9) 0.0403(9) 0.0291(8) -0.0009(7) -0.0052(6) -0.0092(7) N3 0.0530(10) 0.0371(9) 0.0427(10) 0.0023(7) -0.0157(7) -0.0121(7) N4 0.0184(6) 0.0252(6) 0.0254(7) -0.0016(5) 0.0007(5) -0.0047(5) N5 0.0213(6) 0.0235(6) 0.0302(7) 0.0000(5) 0.0002(5) -0.0016(5) N6 0.0452(9) 0.0518(10) 0.0325(8) 0.0045(7) 0.0071(7) -0.0106(8) O1 0.0208(5) 0.0376(6) 0.0265(6) -0.0117(5) 0.0041(4) -0.0058(5) O2 0.0261(6) 0.0247(6) 0.0410(7) 0.0072(5) -0.0074(5) -0.0004(4) O3 0.0200(5) 0.0423(7) 0.0326(6) -0.0183(5) 0.0052(5) -0.0050(5) O4 0.0255(5) 0.0237(6) 0.0523(8) 0.0072(5) -0.0103(5) 0.0010(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 1.9578(12) . ? Cu1 O1 1.9565(11) . ? Cu1 O2 1.9649(11) . ? Cu1 O3 1.9672(11) . ? Cu1 N4 2.2195(12) . ? Cu1 Cu1 2.5873(3) 5_567 ? C1 O2 1.2548(19) . ? C1 O4 1.254(2) 5_567 ? C1 C2 1.520(2) . ? C2 C6 1.518(2) 4_467 ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O1 1.2544(18) 5_567 ? C3 O3 1.2564(19) . ? C3 C4 1.517(2) . ? C4 C5 1.509(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N3 1.481(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N4 1.4853(19) . ? C6 C2 1.518(2) 4_567 ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? N1 N2 1.125(2) . ? N2 N3 1.217(2) . ? N4 N5 1.2409(19) . ? N5 N6 1.122(2) . ? O1 C3 1.2544(19) 5_567 ? O4 C1 1.254(2) 5_567 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cu1 O1 90.02(6) . . ? O4 Cu1 O2 169.51(5) . . ? O1 Cu1 O2 88.45(5) . . ? O4 Cu1 O3 89.90(6) . . ? O1 Cu1 O3 169.64(5) . . ? O2 Cu1 O3 89.74(5) . . ? O4 Cu1 N4 98.77(5) . . ? O1 Cu1 N4 98.96(5) . . ? O2 Cu1 N4 91.72(5) . . ? O3 Cu1 N4 91.29(5) . . ? O4 Cu1 Cu1 84.77(4) . 5_567 ? O1 Cu1 Cu1 86.69(3) . 5_567 ? O2 Cu1 Cu1 84.78(3) . 5_567 ? O3 Cu1 Cu1 82.99(3) . 5_567 ? N4 Cu1 Cu1 173.29(4) . 5_567 ? O2 C1 O4 125.50(14) . 5_567 ? O2 C1 C2 117.05(14) . . ? O4 C1 C2 117.43(14) 5_567 . ? C1 C2 C6 114.54(13) . 4_467 ? C1 C2 H2A 108.6 . . ? C6 C2 H2A 108.6 4_467 . ? C1 C2 H2B 108.6 . . ? C6 C2 H2B 108.6 4_467 . ? H2A C2 H2B 107.6 . . ? O1 C3 O3 125.74(14) 5_567 . ? O1 C3 C4 117.82(13) 5_567 . ? O3 C3 C4 116.42(14) . . ? C5 C4 C3 113.06(14) . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4B 109.0 . . ? C3 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? N3 C5 C4 108.78(15) . . ? N3 C5 H5A 109.9 . . ? C4 C5 H5A 109.9 . . ? N3 C5 H5B 109.9 . . ? C4 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? N4 C6 C2 111.50(12) . 4_567 ? N4 C6 H6A 109.3 . . ? C2 C6 H6A 109.3 4_567 . ? N4 C6 H6B 109.3 . . ? C2 C6 H6B 109.3 4_567 . ? H6A C6 H6B 108.0 . . ? N1 N2 N3 172.5(2) . . ? N2 N3 C5 116.87(16) . . ? N5 N4 C6 116.62(13) . . ? N5 N4 Cu1 115.96(10) . . ? C6 N4 Cu1 125.84(10) . . ? N6 N5 N4 172.57(17) . . ? C3 O1 Cu1 120.34(10) 5_567 . ? C1 O2 Cu1 122.24(10) . . ? C3 O3 Cu1 123.97(10) . . ? C1 O4 Cu1 122.66(10) 5_567 . ? 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 O2 C1 C2 C6 -35.2(2) . . . 4_467 ? O4 C1 C2 C6 146.29(14) 5_567 . . 4_467 ? O1 C3 C4 C5 131.35(16) 5_567 . . . ? O3 C3 C4 C5 -50.4(2) . . . . ? C3 C4 C5 N3 -69.44(18) . . . . ? C4 C5 N3 N2 116.18(19) . . . . ? C2 C6 N4 N5 95.51(16) 4_567 . . . ? C2 C6 N4 Cu1 -69.52(15) 4_567 . . . ? O4 Cu1 N4 N5 123.74(12) . . . . ? O1 Cu1 N4 N5 -144.84(11) . . . . ? O2 Cu1 N4 N5 -56.13(12) . . . . ? O3 Cu1 N4 N5 33.64(12) . . . . ? O4 Cu1 N4 C6 -71.14(13) . . . . ? O1 Cu1 N4 C6 20.28(13) . . . . ? O2 Cu1 N4 C6 108.99(12) . . . . ? O3 Cu1 N4 C6 -161.24(12) . . . . ? O4 Cu1 O1 C3 -86.47(12) . . . 5_567 ? O2 Cu1 O1 C3 83.15(12) . . . 5_567 ? O3 Cu1 O1 C3 3.1(4) . . . 5_567 ? N4 Cu1 O1 C3 174.65(12) . . . 5_567 ? Cu1 Cu1 O1 C3 -1.71(12) 5_567 . . 5_567 ? O4 C1 O2 Cu1 2.8(2) 5_567 . . . ? C2 C1 O2 Cu1 -175.50(10) . . . . ? O4 Cu1 O2 C1 -7.2(4) . . . . ? O1 Cu1 O2 C1 -88.93(13) . . . . ? O3 Cu1 O2 C1 80.88(13) . . . . ? N4 Cu1 O2 C1 172.16(13) . . . . ? Cu1 Cu1 O2 C1 -2.11(12) 5_567 . . . ? O1 C3 O3 Cu1 6.8(2) 5_567 . . . ? C4 C3 O3 Cu1 -171.30(11) . . . . ? O4 Cu1 O3 C3 80.85(14) . . . . ? O1 Cu1 O3 C3 -8.7(4) . . . . ? O2 Cu1 O3 C3 -88.66(14) . . . . ? N4 Cu1 O3 C3 179.63(13) . . . . ? Cu1 Cu1 O3 C3 -3.89(13) 5_567 . . . ? O1 Cu1 O4 C1 86.76(13) . . . 5_567 ? O2 Cu1 O4 C1 5.2(4) . . . 5_567 ? O3 Cu1 O4 C1 -82.88(13) . . . 5_567 ? N4 Cu1 O4 C1 -174.17(13) . . . 5_567 ? Cu1 Cu1 O4 C1 0.09(13) 5_567 . . 5_567 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.346 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.053