data_exp_8294 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H4 Cu2 N12 O' _chemical_formula_weight 351.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 'Cu' 'Cu' -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 9.55130(10) _cell_length_b 14.0864(2) _cell_length_c 7.55280(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1016.18(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 6.28 _cell_measurement_theta_max 63.42 _exptl_crystal_description block _exptl_crystal_colour 'dark blue' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 5.350 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3600 _exptl_absorpt_correction_T_max 0.4815 _exptl_absorpt_process_details 'SADABS (SHELDRICK, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3606 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 6.28 _diffrn_reflns_theta_max 63.42 _reflns_number_total 840 _reflns_number_gt 754 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0666P)^2^+9.6000P] 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 840 _refine_ls_number_parameters 79 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0466 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1289 _refine_ls_wR_factor_gt 0.1255 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.39551(8) 0.12963(5) 0.49412(9) 0.0096(4) Uani 1 1 d . . . N1 N 0.6515(5) -0.0125(3) 0.3689(6) 0.0113(7) Uani 1 1 d . . . N2 N 0.5973(4) 0.0753(3) 0.3845(6) 0.0160(10) Uani 1 1 d . . . N3 N 0.6727(5) 0.1316(3) 0.2831(7) 0.0230(11) Uani 1 1 d . . . N4 N 0.7738(4) 0.0811(3) 0.2037(6) 0.0125(10) Uani 1 1 d . . . N5 N 0.4326(5) 0.2021(3) 0.7214(6) 0.0130(9) Uani 1 1 d . . . N6 N 0.4495(6) 0.1740(4) 0.8867(7) 0.0248(13) Uani 0.50 1 d P . . C2 C 0.4495(6) 0.1740(4) 0.8867(7) 0.0248(13) Uani 0.50 1 d P . . H2 H 0.4543 0.1110 0.9234 0.037 Uiso 0.50 1 calc PR . . N7 N 0.4587(9) 0.2500 0.9940(9) 0.0255(18) Uani 1 2 d S . . O1 O 0.4112(5) 0.2500 0.3837(7) 0.0095(11) Uani 1 2 d S . . H3 H 0.4164 0.2500 0.2702 0.011 Uiso 1 2 d SR . . C1 C 0.7574(5) -0.0076(3) 0.2582(6) 0.0113(7) Uani 1 1 d . . . H1 H 0.8126 -0.0587 0.2233 0.014 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 0.0115(5) 0.0079(5) 0.0093(5) 0.0007(3) -0.0001(3) -0.0008(3) N1 0.0144(15) 0.0082(16) 0.0113(15) -0.0026(14) 0.0028(13) 0.0008(14) N2 0.012(2) 0.013(2) 0.023(3) 0.006(2) 0.0017(19) -0.0027(19) N3 0.019(2) 0.023(3) 0.028(3) 0.006(2) 0.004(2) 0.000(2) N4 0.013(2) 0.011(2) 0.013(2) 0.0001(17) 0.0010(19) -0.0006(19) N5 0.020(2) 0.0096(19) 0.009(2) 0.0010(18) 0.0001(19) -0.0035(19) N6 0.043(3) 0.020(3) 0.011(2) -0.001(2) -0.002(3) 0.003(3) C2 0.043(3) 0.020(3) 0.011(2) -0.001(2) -0.002(3) 0.003(3) N7 0.034(5) 0.027(4) 0.015(4) 0.000 -0.001(3) 0.000 O1 0.014(3) 0.009(2) 0.006(2) 0.000 0.000(2) 0.000 C1 0.0144(15) 0.0082(16) 0.0113(15) -0.0026(14) 0.0028(13) 0.0008(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 O1 1.896(2) . ? Cu1 N1 1.999(4) 5_656 ? Cu1 N4 2.013(4) 6_556 ? Cu1 N5 2.029(4) . ? Cu1 N2 2.233(4) . ? N1 C1 1.315(7) . ? N1 N2 1.345(6) . ? N1 Cu1 1.999(4) 5_656 ? N2 N3 1.317(6) . ? N3 N4 1.340(6) . ? N4 C1 1.325(7) . ? N4 Cu1 2.013(4) 6_656 ? N5 N6 1.319(7) . ? N5 N5 1.349(9) 8_565 ? N6 N7 1.346(6) . ? N7 C2 1.346(6) 8_565 ? N7 N6 1.346(6) 8_565 ? O1 Cu1 1.896(2) 8_565 ? O1 H3 0.8585 . ? C1 H1 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 O1 Cu1 N1 169.75(18) . 5_656 ? O1 Cu1 N4 91.28(19) . 6_556 ? N1 Cu1 N4 88.53(18) 5_656 6_556 ? O1 Cu1 N5 84.74(18) . . ? N1 Cu1 N5 90.97(17) 5_656 . ? N4 Cu1 N5 154.16(18) 6_556 . ? O1 Cu1 N2 94.31(18) . . ? N1 Cu1 N2 95.90(17) 5_656 . ? N4 Cu1 N2 96.14(17) 6_556 . ? N5 Cu1 N2 109.59(18) . . ? C1 N1 N2 107.6(4) . . ? C1 N1 Cu1 123.0(3) . 5_656 ? N2 N1 Cu1 128.9(3) . 5_656 ? N3 N2 N1 107.0(4) . . ? N3 N2 Cu1 118.8(3) . . ? N1 N2 Cu1 132.8(3) . . ? N2 N3 N4 109.5(4) . . ? C1 N4 N3 106.1(4) . . ? C1 N4 Cu1 128.2(3) . 6_656 ? N3 N4 Cu1 124.6(3) . 6_656 ? N6 N5 N5 107.5(3) . 8_565 ? N6 N5 Cu1 132.1(4) . . ? N5 N5 Cu1 120.22(12) 8_565 . ? N5 N6 N7 109.8(5) . . ? C2 N7 N6 0.0(6) 8_565 8_565 ? C2 N7 N6 105.4(6) 8_565 . ? N6 N7 N6 105.4(6) 8_565 . ? Cu1 O1 Cu1 126.9(3) 8_565 . ? Cu1 O1 H3 116.4 8_565 . ? Cu1 O1 H3 116.4 . . ? N1 C1 N4 109.7(4) . . ? N1 C1 H1 125.1 . . ? N4 C1 H1 125.1 . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 63.42 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.469 _refine_diff_density_min -0.629 _refine_diff_density_rms 0.116