#============================================================================== data_global loop_ _journal_name_full 'European Journal of Chemistry' _journal_coden_ASTM EJCUA9 _journal_volume 10 _journal_issue 3 _journal_year 2019 _journal_page_first 195 _journal_page_last 200 #=============================================================================== data_k12adb02 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H13 Cu N5 O4' _chemical_formula_weight 318.78 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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9550(2) _cell_length_b 7.9810(2) _cell_length_c 11.0660(3) _cell_angle_alpha 76.328(1) _cell_angle_beta 71.115(1) _cell_angle_gamma 84.577(1) _cell_volume 645.79(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 15243 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 326 _exptl_absorpt_coefficient_mu 1.709 # Absorption correction _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.886 _exptl_absorpt_correction_T_max 0.920 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11111 _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_av_sigmaI/netI 0.0556 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2951 _reflns_number_gt 2410 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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. Asymmetric unit consist of one Cu(I) centre, 3 independent pyrazine halves, each of which straddles a crystallographic inversion centre, one nitrate anion and one guest DMF molecule. Overall, the structure consists of parallel 2-D sheets. ; _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^)+(0.0223P)^2^+0.2453P] 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 2951 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0727 _refine_ls_wR_factor_gt 0.0669 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.29077(4) 0.26089(3) 0.79824(2) 0.02253(10) Uani 1 1 d . . . O1 O 0.0949(2) 0.0866(2) 0.80282(16) 0.0321(4) Uani 1 1 d . . . O2 O 0.0577(2) -0.1660(2) 0.77473(19) 0.0425(5) Uani 1 1 d . . . O3 O 0.3175(2) -0.0515(2) 0.69201(17) 0.0379(4) Uani 1 1 d . . . O4 O 0.6154(2) 0.5179(2) 0.80893(18) 0.0388(4) Uani 1 1 d . . . N1 N 0.4048(2) 0.3969(2) 0.62060(16) 0.0196(4) Uani 1 1 d . . . N2 N 0.1171(2) 0.4088(2) 0.91297(17) 0.0210(4) Uani 1 1 d . . . N3 N 0.4182(2) 0.1096(2) 0.91529(16) 0.0201(4) Uani 1 1 d . . . N4 N 0.1571(3) -0.0461(2) 0.75650(18) 0.0246(4) Uani 1 1 d . . . N5 N 0.7512(3) 0.7541(3) 0.6594(2) 0.0311(5) Uani 1 1 d . . . C1 C 0.5035(3) 0.3286(3) 0.5194(2) 0.0208(5) Uani 1 1 d . . . H1 H 0.5086 0.2069 0.5297 0.025 Uiso 1 1 calc R . . C2 C 0.4024(3) 0.5706(3) 0.5989(2) 0.0201(5) Uani 1 1 d . . . H2 H 0.3338 0.6252 0.6672 0.024 Uiso 1 1 calc R . . C3 C 0.1734(3) 0.4899(3) 0.9850(2) 0.0241(5) Uani 1 1 d . . . H3 H 0.2963 0.4854 0.9767 0.029 Uiso 1 1 calc R . . C4 C -0.0576(3) 0.4197(3) 0.9289(2) 0.0238(5) Uani 1 1 d . . . H4 H -0.1030 0.3637 0.8795 0.029 Uiso 1 1 calc R . . C5 C 0.3281(3) -0.0125(3) 1.0159(2) 0.0233(5) Uani 1 1 d . . . H5 H 0.2050 -0.0246 1.0305 0.028 Uiso 1 1 calc R . . C6 C 0.5908(3) 0.1209(3) 0.9015(2) 0.0238(5) Uani 1 1 d . . . H6 H 0.6595 0.2065 0.8325 0.029 Uiso 1 1 calc R . . C7 C 0.6282(3) 0.6744(3) 0.7665(2) 0.0310(6) Uani 1 1 d . . . H7 H 0.5425 0.7454 0.8145 0.037 Uiso 1 1 calc R . . C8 C 0.7580(4) 0.9409(3) 0.6192(3) 0.0365(6) Uani 1 1 d . . . H8A H 0.6504 0.9915 0.6721 0.055 Uiso 1 1 calc R . . H8B H 0.7654 0.9764 0.5266 0.055 Uiso 1 1 calc R . . H8C H 0.8627 0.9807 0.6317 0.055 Uiso 1 1 calc R . . C9 C 0.8898(4) 0.6562(4) 0.5822(3) 0.0479(7) Uani 1 1 d . . . H9A H 1.0042 0.6766 0.5912 0.072 Uiso 1 1 calc R . . H9B H 0.8954 0.6928 0.4900 0.072 Uiso 1 1 calc R . . H9C H 0.8635 0.5331 0.6131 0.072 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 0.02470(16) 0.02090(15) 0.01916(15) -0.00260(11) -0.00449(11) 0.00036(11) O1 0.0254(9) 0.0284(9) 0.0424(10) -0.0182(8) -0.0027(7) -0.0015(7) O2 0.0443(11) 0.0286(9) 0.0577(12) -0.0115(9) -0.0153(9) -0.0130(8) O3 0.0282(10) 0.0370(10) 0.0462(11) -0.0190(8) -0.0024(8) 0.0026(8) O4 0.0417(11) 0.0305(10) 0.0487(11) -0.0053(8) -0.0224(9) -0.0007(8) N1 0.0214(9) 0.0195(9) 0.0180(9) -0.0046(7) -0.0061(7) 0.0001(7) N2 0.0226(9) 0.0203(9) 0.0196(9) -0.0031(7) -0.0067(8) -0.0005(8) N3 0.0200(9) 0.0181(9) 0.0196(9) -0.0031(7) -0.0033(7) -0.0015(7) N4 0.0294(11) 0.0221(10) 0.0237(10) -0.0042(8) -0.0101(9) -0.0024(8) N5 0.0294(11) 0.0307(11) 0.0350(11) -0.0135(9) -0.0094(9) 0.0052(9) C1 0.0253(11) 0.0172(10) 0.0210(11) -0.0040(9) -0.0091(9) 0.0004(9) C2 0.0226(11) 0.0199(11) 0.0187(11) -0.0062(9) -0.0064(9) 0.0008(9) C3 0.0195(11) 0.0265(12) 0.0268(12) -0.0061(10) -0.0079(9) -0.0001(9) C4 0.0254(12) 0.0264(12) 0.0239(11) -0.0101(10) -0.0101(10) -0.0015(10) C5 0.0187(11) 0.0246(11) 0.0229(11) -0.0024(9) -0.0030(9) -0.0026(9) C6 0.0250(12) 0.0220(11) 0.0203(11) -0.0003(9) -0.0033(9) -0.0048(9) C7 0.0308(13) 0.0356(14) 0.0326(13) -0.0115(11) -0.0164(11) 0.0045(11) C8 0.0381(15) 0.0347(14) 0.0341(14) -0.0057(11) -0.0097(12) 0.0022(12) C9 0.0407(16) 0.0493(17) 0.0542(18) -0.0266(14) -0.0076(14) 0.0090(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 1.9720(17) . ? Cu1 N3 2.0108(17) . ? Cu1 N2 2.0443(18) . ? Cu1 O1 2.1660(16) . ? O1 N4 1.274(2) . ? O2 N4 1.237(2) . ? O3 N4 1.246(2) . ? O4 C7 1.227(3) . ? N1 C1 1.344(3) . ? N1 C2 1.349(3) . ? N2 C3 1.335(3) . ? N2 C4 1.340(3) . ? N3 C6 1.341(3) . ? N3 C5 1.344(3) . ? N5 C7 1.333(3) . ? N5 C9 1.449(3) . ? N5 C8 1.452(3) . ? C1 C2 1.380(3) 2_666 ? C1 H1 0.9500 . ? C2 C1 1.380(3) 2_666 ? C2 H2 0.9500 . ? C3 C4 1.382(3) 2_567 ? C3 H3 0.9500 . ? C4 C3 1.382(3) 2_567 ? C4 H4 0.9500 . ? C5 C6 1.380(3) 2_657 ? C5 H5 0.9500 . ? C6 C5 1.380(3) 2_657 ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? 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 N3 125.60(7) . . ? N1 Cu1 N2 111.52(7) . . ? N3 Cu1 N2 105.15(7) . . ? N1 Cu1 O1 112.54(7) . . ? N3 Cu1 O1 101.48(7) . . ? N2 Cu1 O1 96.28(7) . . ? N4 O1 Cu1 115.53(13) . . ? C1 N1 C2 115.77(17) . . ? C1 N1 Cu1 124.28(14) . . ? C2 N1 Cu1 119.56(14) . . ? C3 N2 C4 116.43(18) . . ? C3 N2 Cu1 120.06(14) . . ? C4 N2 Cu1 123.31(15) . . ? C6 N3 C5 115.88(18) . . ? C6 N3 Cu1 124.67(14) . . ? C5 N3 Cu1 119.45(14) . . ? O2 N4 O3 121.20(19) . . ? O2 N4 O1 119.75(19) . . ? O3 N4 O1 119.05(19) . . ? C7 N5 C9 120.7(2) . . ? C7 N5 C8 121.9(2) . . ? C9 N5 C8 117.3(2) . . ? N1 C1 C2 122.22(19) . 2_666 ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 2_666 . ? N1 C2 C1 122.01(19) . 2_666 ? N1 C2 H2 119.0 . . ? C1 C2 H2 119.0 2_666 . ? N2 C3 C4 121.7(2) . 2_567 ? N2 C3 H3 119.1 . . ? C4 C3 H3 119.1 2_567 . ? N2 C4 C3 121.8(2) . 2_567 ? N2 C4 H4 119.1 . . ? C3 C4 H4 119.1 2_567 . ? N3 C5 C6 121.9(2) . 2_657 ? N3 C5 H5 119.1 . . ? C6 C5 H5 119.1 2_657 . ? N3 C6 C5 122.22(19) . 2_657 ? N3 C6 H6 118.9 . . ? C5 C6 H6 118.9 2_657 . ? O4 C7 N5 126.1(2) . . ? O4 C7 H7 117.0 . . ? N5 C7 H7 117.0 . . ? N5 C8 H8A 109.5 . . ? N5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N5 C9 H9A 109.5 . . ? N5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? 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 N1 Cu1 O1 N4 74.01(16) . . . . ? N3 Cu1 O1 N4 -62.66(15) . . . . ? N2 Cu1 O1 N4 -169.56(14) . . . . ? N3 Cu1 N1 C1 61.63(19) . . . . ? N2 Cu1 N1 C1 -169.49(16) . . . . ? O1 Cu1 N1 C1 -62.58(18) . . . . ? N3 Cu1 N1 C2 -110.90(16) . . . . ? N2 Cu1 N1 C2 17.98(18) . . . . ? O1 Cu1 N1 C2 124.89(16) . . . . ? N1 Cu1 N2 C3 -90.51(16) . . . . ? N3 Cu1 N2 C3 48.51(17) . . . . ? O1 Cu1 N2 C3 152.24(16) . . . . ? N1 Cu1 N2 C4 94.87(17) . . . . ? N3 Cu1 N2 C4 -126.11(17) . . . . ? O1 Cu1 N2 C4 -22.38(17) . . . . ? N1 Cu1 N3 C6 19.3(2) . . . . ? N2 Cu1 N3 C6 -112.07(18) . . . . ? O1 Cu1 N3 C6 148.10(17) . . . . ? N1 Cu1 N3 C5 -161.00(15) . . . . ? N2 Cu1 N3 C5 67.61(17) . . . . ? O1 Cu1 N3 C5 -32.21(17) . . . . ? Cu1 O1 N4 O2 167.97(15) . . . . ? Cu1 O1 N4 O3 -12.9(2) . . . . ? C2 N1 C1 C2 0.5(3) . . . 2_666 ? Cu1 N1 C1 C2 -172.30(16) . . . 2_666 ? C1 N1 C2 C1 -0.5(3) . . . 2_666 ? Cu1 N1 C2 C1 172.66(16) . . . 2_666 ? C4 N2 C3 C4 0.0(3) . . . 2_567 ? Cu1 N2 C3 C4 -175.01(16) . . . 2_567 ? C3 N2 C4 C3 0.0(3) . . . 2_567 ? Cu1 N2 C4 C3 174.83(16) . . . 2_567 ? C6 N3 C5 C6 -0.9(4) . . . 2_657 ? Cu1 N3 C5 C6 179.39(16) . . . 2_657 ? C5 N3 C6 C5 0.9(4) . . . 2_657 ? Cu1 N3 C6 C5 -179.41(16) . . . 2_657 ? C9 N5 C7 O4 -1.6(4) . . . . ? C8 N5 C7 O4 -178.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.316 _refine_diff_density_min -0.649 _refine_diff_density_rms 0.091 data_c:\users\swifts\desktop\k12adb02\k12adb02 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H13 Cu N5 O4' _chemical_formula_weight 318.78 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' 'Cu' 'Cu' 0.3201 1.2651 '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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9550(2) _cell_length_b 7.9810(2) _cell_length_c 11.0660(3) _cell_angle_alpha 76.3280(10) _cell_angle_beta 71.1150(10) _cell_angle_gamma 84.5770(10) _cell_volume 645.79(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 326 _exptl_absorpt_coefficient_mu 1.709 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.7261 _exptl_absorpt_correction_T_max 0.9194 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _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 11111 _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_av_sigmaI/netI 0.0556 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2951 _reflns_number_gt 2410 _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^)+(0.0223P)^2^+0.2453P] 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 2951 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0727 _refine_ls_wR_factor_gt 0.0669 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.29077(4) 0.26089(3) 0.79824(2) 0.02253(10) Uani 1 1 d . . . O1 O 0.0949(2) 0.0866(2) 0.80282(16) 0.0321(4) Uani 1 1 d . . . O2 O 0.0577(2) -0.1660(2) 0.77473(19) 0.0425(5) Uani 1 1 d . . . O3 O 0.3175(2) -0.0515(2) 0.69201(17) 0.0379(4) Uani 1 1 d . . . O4 O 0.6154(2) 0.5179(2) 0.80893(18) 0.0388(4) Uani 1 1 d . . . N1 N 0.4048(2) 0.3969(2) 0.62060(16) 0.0196(4) Uani 1 1 d . . . N2 N 0.1171(2) 0.4088(2) 0.91297(17) 0.0210(4) Uani 1 1 d . . . N3 N 0.4182(2) 0.1096(2) 0.91529(16) 0.0201(4) Uani 1 1 d . . . N4 N 0.1571(3) -0.0461(2) 0.75650(18) 0.0246(4) Uani 1 1 d . . . N5 N 0.7512(3) 0.7541(3) 0.6594(2) 0.0311(5) Uani 1 1 d . . . C1 C 0.5035(3) 0.3286(3) 0.5194(2) 0.0208(5) Uani 1 1 d . . . H1 H 0.5086 0.2069 0.5297 0.025 Uiso 1 1 calc R . . C2 C 0.4024(3) 0.5706(3) 0.5989(2) 0.0201(5) Uani 1 1 d . . . H2 H 0.3338 0.6252 0.6672 0.024 Uiso 1 1 calc R . . C3 C 0.1734(3) 0.4899(3) 0.9850(2) 0.0241(5) Uani 1 1 d . . . H3 H 0.2963 0.4854 0.9767 0.029 Uiso 1 1 calc R . . C4 C -0.0576(3) 0.4197(3) 0.9289(2) 0.0238(5) Uani 1 1 d . . . H4 H -0.1030 0.3637 0.8795 0.029 Uiso 1 1 calc R . . C5 C 0.3281(3) -0.0125(3) 1.0159(2) 0.0233(5) Uani 1 1 d . . . H5 H 0.2050 -0.0246 1.0305 0.028 Uiso 1 1 calc R . . C6 C 0.5908(3) 0.1209(3) 0.9015(2) 0.0238(5) Uani 1 1 d . . . H6 H 0.6595 0.2065 0.8325 0.029 Uiso 1 1 calc R . . C7 C 0.6282(3) 0.6744(3) 0.7665(2) 0.0310(6) Uani 1 1 d . . . H7 H 0.5425 0.7454 0.8145 0.037 Uiso 1 1 calc R . . C8 C 0.7580(4) 0.9409(3) 0.6192(3) 0.0365(6) Uani 1 1 d . . . H8A H 0.6504 0.9915 0.6721 0.055 Uiso 1 1 calc R . . H8B H 0.7654 0.9764 0.5266 0.055 Uiso 1 1 calc R . . H8C H 0.8627 0.9807 0.6317 0.055 Uiso 1 1 calc R . . C9 C 0.8898(4) 0.6562(4) 0.5822(3) 0.0479(7) Uani 1 1 d . . . H9A H 1.0042 0.6766 0.5912 0.072 Uiso 1 1 calc R . . H9B H 0.8954 0.6928 0.4900 0.072 Uiso 1 1 calc R . . H9C H 0.8635 0.5331 0.6131 0.072 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 0.02470(16) 0.02090(15) 0.01916(15) -0.00260(11) -0.00449(11) 0.00036(11) O1 0.0254(9) 0.0284(9) 0.0424(10) -0.0182(8) -0.0027(7) -0.0015(7) O2 0.0443(11) 0.0286(9) 0.0577(12) -0.0115(9) -0.0153(9) -0.0130(8) O3 0.0282(10) 0.0370(10) 0.0462(11) -0.0190(8) -0.0024(8) 0.0026(8) O4 0.0417(11) 0.0305(10) 0.0487(11) -0.0053(8) -0.0224(9) -0.0007(8) N1 0.0214(9) 0.0195(9) 0.0180(9) -0.0046(7) -0.0061(7) 0.0001(7) N2 0.0226(9) 0.0203(9) 0.0196(9) -0.0031(7) -0.0067(8) -0.0005(8) N3 0.0200(9) 0.0181(9) 0.0196(9) -0.0031(7) -0.0033(7) -0.0015(7) N4 0.0294(11) 0.0221(10) 0.0237(10) -0.0042(8) -0.0101(9) -0.0024(8) N5 0.0294(11) 0.0307(11) 0.0350(11) -0.0135(9) -0.0094(9) 0.0052(9) C1 0.0253(11) 0.0172(10) 0.0210(11) -0.0040(9) -0.0091(9) 0.0004(9) C2 0.0226(11) 0.0199(11) 0.0187(11) -0.0062(9) -0.0064(9) 0.0008(9) C3 0.0195(11) 0.0265(12) 0.0268(12) -0.0061(10) -0.0079(9) -0.0001(9) C4 0.0254(12) 0.0264(12) 0.0239(11) -0.0101(10) -0.0101(10) -0.0015(10) C5 0.0187(11) 0.0246(11) 0.0229(11) -0.0024(9) -0.0030(9) -0.0026(9) C6 0.0250(12) 0.0220(11) 0.0203(11) -0.0003(9) -0.0033(9) -0.0048(9) C7 0.0308(13) 0.0356(14) 0.0326(13) -0.0115(11) -0.0164(11) 0.0045(11) C8 0.0381(15) 0.0347(14) 0.0341(14) -0.0057(11) -0.0097(12) 0.0022(12) C9 0.0407(16) 0.0493(17) 0.0542(18) -0.0266(14) -0.0076(14) 0.0090(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 1.9720(17) . ? Cu1 N3 2.0108(17) . ? Cu1 N2 2.0443(18) . ? Cu1 O1 2.1660(16) . ? O1 N4 1.274(2) . ? O2 N4 1.237(2) . ? O3 N4 1.246(2) . ? O4 C7 1.227(3) . ? N1 C1 1.344(3) . ? N1 C2 1.349(3) . ? N2 C3 1.335(3) . ? N2 C4 1.340(3) . ? N3 C6 1.341(3) . ? N3 C5 1.344(3) . ? N5 C7 1.333(3) . ? N5 C9 1.449(3) . ? N5 C8 1.452(3) . ? C1 C2 1.380(3) 2_666 ? C1 H1 0.9500 . ? C2 C1 1.380(3) 2_666 ? C2 H2 0.9500 . ? C3 C4 1.382(3) 2_567 ? C3 H3 0.9500 . ? C4 C3 1.382(3) 2_567 ? C4 H4 0.9500 . ? C5 C6 1.380(3) 2_657 ? C5 H5 0.9500 . ? C6 C5 1.380(3) 2_657 ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? 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 N3 125.60(7) . . ? N1 Cu1 N2 111.52(7) . . ? N3 Cu1 N2 105.15(7) . . ? N1 Cu1 O1 112.54(7) . . ? N3 Cu1 O1 101.48(7) . . ? N2 Cu1 O1 96.28(7) . . ? N4 O1 Cu1 115.53(13) . . ? C1 N1 C2 115.77(17) . . ? C1 N1 Cu1 124.28(14) . . ? C2 N1 Cu1 119.56(14) . . ? C3 N2 C4 116.43(18) . . ? C3 N2 Cu1 120.06(14) . . ? C4 N2 Cu1 123.31(15) . . ? C6 N3 C5 115.88(18) . . ? C6 N3 Cu1 124.67(14) . . ? C5 N3 Cu1 119.45(14) . . ? O2 N4 O3 121.20(19) . . ? O2 N4 O1 119.75(19) . . ? O3 N4 O1 119.05(19) . . ? C7 N5 C9 120.7(2) . . ? C7 N5 C8 121.9(2) . . ? C9 N5 C8 117.3(2) . . ? N1 C1 C2 122.22(19) . 2_666 ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 2_666 . ? N1 C2 C1 122.01(19) . 2_666 ? N1 C2 H2 119.0 . . ? C1 C2 H2 119.0 2_666 . ? N2 C3 C4 121.7(2) . 2_567 ? N2 C3 H3 119.1 . . ? C4 C3 H3 119.1 2_567 . ? N2 C4 C3 121.8(2) . 2_567 ? N2 C4 H4 119.1 . . ? C3 C4 H4 119.1 2_567 . ? N3 C5 C6 121.9(2) . 2_657 ? N3 C5 H5 119.1 . . ? C6 C5 H5 119.1 2_657 . ? N3 C6 C5 122.22(19) . 2_657 ? N3 C6 H6 118.9 . . ? C5 C6 H6 118.9 2_657 . ? O4 C7 N5 126.1(2) . . ? O4 C7 H7 117.0 . . ? N5 C7 H7 117.0 . . ? N5 C8 H8A 109.5 . . ? N5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N5 C9 H9A 109.5 . . ? N5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? 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 N1 Cu1 O1 N4 74.01(16) . . . . ? N3 Cu1 O1 N4 -62.66(15) . . . . ? N2 Cu1 O1 N4 -169.56(14) . . . . ? N3 Cu1 N1 C1 61.63(19) . . . . ? N2 Cu1 N1 C1 -169.49(16) . . . . ? O1 Cu1 N1 C1 -62.58(18) . . . . ? N3 Cu1 N1 C2 -110.90(16) . . . . ? N2 Cu1 N1 C2 17.98(18) . . . . ? O1 Cu1 N1 C2 124.89(16) . . . . ? N1 Cu1 N2 C3 -90.51(16) . . . . ? N3 Cu1 N2 C3 48.51(17) . . . . ? O1 Cu1 N2 C3 152.24(16) . . . . ? N1 Cu1 N2 C4 94.87(17) . . . . ? N3 Cu1 N2 C4 -126.11(17) . . . . ? O1 Cu1 N2 C4 -22.38(17) . . . . ? N1 Cu1 N3 C6 19.3(2) . . . . ? N2 Cu1 N3 C6 -112.07(18) . . . . ? O1 Cu1 N3 C6 148.10(17) . . . . ? N1 Cu1 N3 C5 -161.00(15) . . . . ? N2 Cu1 N3 C5 67.61(17) . . . . ? O1 Cu1 N3 C5 -32.21(17) . . . . ? Cu1 O1 N4 O2 167.97(15) . . . . ? Cu1 O1 N4 O3 -12.9(2) . . . . ? C2 N1 C1 C2 0.5(3) . . . 2_666 ? Cu1 N1 C1 C2 -172.30(16) . . . 2_666 ? C1 N1 C2 C1 -0.5(3) . . . 2_666 ? Cu1 N1 C2 C1 172.66(16) . . . 2_666 ? C4 N2 C3 C4 0.0(3) . . . 2_567 ? Cu1 N2 C3 C4 -175.01(16) . . . 2_567 ? C3 N2 C4 C3 0.0(3) . . . 2_567 ? Cu1 N2 C4 C3 174.83(16) . . . 2_567 ? C6 N3 C5 C6 -0.9(4) . . . 2_657 ? Cu1 N3 C5 C6 179.39(16) . . . 2_657 ? C5 N3 C6 C5 0.9(4) . . . 2_657 ? Cu1 N3 C6 C5 -179.41(16) . . . 2_657 ? C9 N5 C7 O4 -1.6(4) . . . . ? C8 N5 C7 O4 -178.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.316 _refine_diff_density_min -0.649 _refine_diff_density_rms 0.091