data_UTSA-100 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H5 Cu N5 O4' _chemical_formula_weight 310.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 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 'P bc n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 12.1905(11) _cell_length_b 14.4177(13) _cell_length_c 20.4894(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3601.2(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100.33(10) _cell_measurement_reflns_used 3168 _cell_measurement_theta_min 4.2560 _cell_measurement_theta_max 72.1070 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.146 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 1.858 _exptl_absorpt_correction_T_min 0.47184 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.33(10) _diffrn_ambient_environment 'air' _diffrn_source 'sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _diffrn_radiation_probe 'x-ray' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_monochromator 'mirror' _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Atlas' _diffrn_detector_area_resol_mean 10.5148 _diffrn_measurement_method '\w scans' _diffrn_standards_number 39044 _diffrn_standards_interval_count 1 _diffrn_standards_interval_time 12.5000 _diffrn_standards_decay_% none _diffrn_reflns_number 3222 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0732 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.32 _diffrn_reflns_theta_max 67.07 _reflns_number_total 3222 _reflns_number_gt 1994 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _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^)+(0.1795P)^2^+0.0000P] 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 3222 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1106 _refine_ls_R_factor_gt 0.0871 _refine_ls_wR_factor_ref 0.2569 _refine_ls_wR_factor_gt 0.2303 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 0.961 _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 C1 C 0.1411(5) 0.3672(4) 0.4462(3) 0.0378(13) Uani 1 1 d . . . C2 C 0.2430(5) 0.3752(4) 0.5559(3) 0.0426(15) Uani 1 1 d . . . C3 C 0.1758(5) 0.4420(5) 0.5885(3) 0.0471(16) Uani 1 1 d . . . H3 H 0.1298 0.4818 0.5655 0.057 Uiso 1 1 calc R . . C4 C 0.1825(5) 0.4448(4) 0.6561(3) 0.0388(14) Uani 1 1 d . . . C5 C 0.2511(4) 0.3823(4) 0.6896(3) 0.0381(13) Uani 1 1 d . . . H5 H 0.2529 0.3829 0.7349 0.046 Uiso 1 1 calc R . . C6 C 0.3149(5) 0.3210(4) 0.6562(3) 0.0375(13) Uani 1 1 d . . . C7 C 0.3113(5) 0.3203(5) 0.5882(3) 0.0449(15) Uani 1 1 d . . . H7 H 0.3575 0.2807 0.5652 0.054 Uiso 1 1 calc R . . C8 C 0.3864(5) 0.2553(4) 0.6932(3) 0.0349(13) Uani 1 1 d . . . C9 C 0.1124(5) 0.5133(4) 0.6932(3) 0.0326(12) Uani 1 1 d . . . Cu1 Cu 0.07196(6) 0.63494(5) 0.79985(4) 0.0278(3) Uani 1 1 d . . . N1 N 0.1767(4) 0.3649(3) 0.3860(2) 0.0353(11) Uani 1 1 d . . . N2 N 0.2898(5) 0.3675(4) 0.3872(3) 0.0546(16) Uani 1 1 d . . . N3 N 0.3254(5) 0.3703(4) 0.4463(3) 0.0492(14) Uani 1 1 d . . . N4 N 0.2315(5) 0.3706(3) 0.4861(2) 0.0445(13) Uani 1 1 d . . . N5 N 0.0362(5) 0.3666(4) 0.4690(3) 0.0614(17) Uani 1 1 d . . . H5B H -0.0179 0.3643 0.4421 0.074 Uiso 1 1 calc R . . H5A H 0.0240 0.3684 0.5104 0.074 Uiso 1 1 calc R . . O1 O 0.4696(3) 0.2246(3) 0.66187(19) 0.0412(10) Uani 1 1 d . . . O2 O 0.1443(3) 0.7331(3) 0.74834(19) 0.0403(10) Uani 1 1 d . . . O3 O 0.1460(3) 0.5386(3) 0.74760(19) 0.0384(9) Uani 1 1 d . . . O4 O 0.0258(3) 0.5390(3) 0.66489(19) 0.0402(10) 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 C1 0.037(3) 0.043(3) 0.033(3) -0.004(2) -0.008(2) 0.015(3) C2 0.046(3) 0.055(4) 0.026(3) 0.003(2) -0.006(2) 0.021(3) C3 0.064(4) 0.049(4) 0.029(3) -0.007(3) -0.012(3) 0.021(3) C4 0.056(4) 0.034(3) 0.027(3) 0.003(2) -0.005(2) 0.007(3) C5 0.032(3) 0.065(4) 0.018(3) 0.001(2) -0.0036(19) 0.011(3) C6 0.049(3) 0.028(3) 0.036(3) 0.005(2) -0.001(2) 0.004(2) C7 0.053(4) 0.044(4) 0.037(3) -0.006(3) 0.007(3) 0.007(3) C8 0.040(3) 0.023(3) 0.041(4) -0.005(2) -0.002(2) 0.005(2) C9 0.048(3) 0.026(3) 0.024(3) -0.001(2) -0.003(2) 0.007(2) Cu1 0.0323(5) 0.0260(5) 0.0250(5) 0.0000(3) 0.0012(3) -0.0005(3) N1 0.038(3) 0.047(3) 0.021(2) -0.0002(19) -0.0006(18) 0.008(2) N2 0.065(4) 0.068(4) 0.031(3) 0.000(2) -0.004(3) 0.031(3) N3 0.051(3) 0.069(4) 0.027(3) -0.001(2) -0.005(2) 0.019(3) N4 0.060(3) 0.053(3) 0.021(3) -0.0029(19) 0.001(2) 0.030(3) N5 0.045(3) 0.099(5) 0.041(3) -0.007(3) -0.004(3) 0.001(3) O1 0.044(2) 0.048(2) 0.032(2) 0.0050(17) 0.0016(17) 0.0158(19) O2 0.053(2) 0.041(2) 0.027(2) 0.0064(16) -0.0047(18) -0.0108(19) O3 0.045(2) 0.033(2) 0.037(2) -0.0055(16) -0.0046(18) 0.0098(17) O4 0.045(2) 0.041(2) 0.035(2) -0.0151(17) -0.0042(18) 0.0149(19) _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 C1 N1 1.308(8) . ? C1 N5 1.361(9) . ? C1 N4 1.372(8) . ? C2 C7 1.326(8) . ? C2 C3 1.431(8) . ? C2 N4 1.440(8) . ? C3 C4 1.388(8) . ? C3 H3 0.9300 . ? C4 C5 1.408(7) . ? C4 C9 1.511(8) . ? C5 C6 1.361(8) . ? C5 H5 0.9300 . ? C6 C7 1.394(8) . ? C6 C8 1.493(8) . ? C7 H7 0.9300 . ? C8 O2 1.232(7) 7_655 ? C8 O1 1.280(7) . ? C9 O3 1.242(6) . ? C9 O4 1.260(7) . ? Cu1 O1 1.961(4) 6_567 ? Cu1 O4 1.964(4) 4_556 ? Cu1 O3 1.973(4) . ? Cu1 O2 1.973(4) . ? Cu1 N1 2.178(5) 8_566 ? Cu1 Cu1 2.6927(15) 4_556 ? N1 N2 1.380(8) . ? N1 Cu1 2.178(5) 8_565 ? N2 N3 1.288(8) . ? N3 N4 1.405(7) . ? N5 H5B 0.8600 . ? N5 H5A 0.8600 . ? O1 Cu1 1.961(4) 6_657 ? O2 C8 1.232(7) 7_665 ? O4 Cu1 1.964(4) 4_556 ? 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 C1 N5 129.4(5) . . ? N1 C1 N4 107.2(5) . . ? N5 C1 N4 123.3(6) . . ? C7 C2 C3 122.0(6) . . ? C7 C2 N4 122.0(5) . . ? C3 C2 N4 116.0(5) . . ? C4 C3 C2 116.8(5) . . ? C4 C3 H3 121.6 . . ? C2 C3 H3 121.6 . . ? C3 C4 C5 120.2(5) . . ? C3 C4 C9 119.2(5) . . ? C5 C4 C9 120.6(5) . . ? C6 C5 C4 120.7(6) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 119.2(5) . . ? C5 C6 C8 119.3(5) . . ? C7 C6 C8 121.4(5) . . ? C2 C7 C6 120.9(6) . . ? C2 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? O2 C8 O1 127.6(5) 7_655 . ? O2 C8 C6 117.0(5) 7_655 . ? O1 C8 C6 115.2(5) . . ? O3 C9 O4 127.1(5) . . ? O3 C9 C4 117.2(5) . . ? O4 C9 C4 115.7(5) . . ? O1 Cu1 O4 86.05(19) 6_567 4_556 ? O1 Cu1 O3 166.61(17) 6_567 . ? O4 Cu1 O3 88.92(18) 4_556 . ? O1 Cu1 O2 91.45(18) 6_567 . ? O4 Cu1 O2 166.69(17) 4_556 . ? O3 Cu1 O2 90.60(19) . . ? O1 Cu1 N1 92.75(18) 6_567 8_566 ? O4 Cu1 N1 93.35(17) 4_556 8_566 ? O3 Cu1 N1 99.93(17) . 8_566 ? O2 Cu1 N1 99.83(17) . 8_566 ? O1 Cu1 Cu1 83.61(12) 6_567 4_556 ? O4 Cu1 Cu1 83.32(12) 4_556 4_556 ? O3 Cu1 Cu1 83.48(12) . 4_556 ? O2 Cu1 Cu1 83.42(12) . 4_556 ? N1 Cu1 Cu1 175.21(13) 8_566 4_556 ? C1 N1 N2 108.3(5) . . ? C1 N1 Cu1 124.7(4) . 8_565 ? N2 N1 Cu1 126.8(4) . 8_565 ? N3 N2 N1 110.7(5) . . ? N2 N3 N4 105.7(5) . . ? C1 N4 N3 108.0(5) . . ? C1 N4 C2 132.2(6) . . ? N3 N4 C2 119.8(5) . . ? C1 N5 H5B 120.0 . . ? C1 N5 H5A 120.0 . . ? H5B N5 H5A 120.0 . . ? C8 O1 Cu1 122.1(4) . 6_657 ? C8 O2 Cu1 122.8(4) 7_665 . ? C9 O3 Cu1 122.9(4) . . ? C9 O4 Cu1 123.1(3) . 4_556 ? 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 C7 C2 C3 C4 -2.1(10) . . . . ? N4 C2 C3 C4 177.4(6) . . . . ? C2 C3 C4 C5 -1.4(10) . . . . ? C2 C3 C4 C9 -179.3(6) . . . . ? C3 C4 C5 C6 2.6(9) . . . . ? C9 C4 C5 C6 -179.5(6) . . . . ? C4 C5 C6 C7 -0.3(9) . . . . ? C4 C5 C6 C8 -179.7(5) . . . . ? C3 C2 C7 C6 4.5(11) . . . . ? N4 C2 C7 C6 -175.0(6) . . . . ? C5 C6 C7 C2 -3.3(10) . . . . ? C8 C6 C7 C2 176.1(6) . . . . ? C5 C6 C8 O2 27.9(8) . . . 7_655 ? C7 C6 C8 O2 -151.5(6) . . . 7_655 ? C5 C6 C8 O1 -156.0(6) . . . . ? C7 C6 C8 O1 24.6(8) . . . . ? C3 C4 C9 O3 -154.4(6) . . . . ? C5 C4 C9 O3 27.7(8) . . . . ? C3 C4 C9 O4 25.2(9) . . . . ? C5 C4 C9 O4 -152.8(6) . . . . ? N5 C1 N1 N2 179.6(6) . . . . ? N4 C1 N1 N2 -0.5(7) . . . . ? N5 C1 N1 Cu1 2.9(9) . . . 8_565 ? N4 C1 N1 Cu1 -177.2(3) . . . 8_565 ? C1 N1 N2 N3 0.8(8) . . . . ? Cu1 N1 N2 N3 177.4(4) 8_565 . . . ? N1 N2 N3 N4 -0.7(7) . . . . ? N1 C1 N4 N3 0.1(6) . . . . ? N5 C1 N4 N3 180.0(6) . . . . ? N1 C1 N4 C2 179.3(5) . . . . ? N5 C1 N4 C2 -0.8(10) . . . . ? N2 N3 N4 C1 0.4(6) . . . . ? N2 N3 N4 C2 -178.9(5) . . . . ? C7 C2 N4 C1 132.5(7) . . . . ? C3 C2 N4 C1 -47.1(10) . . . . ? C7 C2 N4 N3 -48.5(9) . . . . ? C3 C2 N4 N3 132.0(6) . . . . ? O2 C8 O1 Cu1 -2.6(9) 7_655 . . 6_657 ? C6 C8 O1 Cu1 -178.2(4) . . . 6_657 ? O1 Cu1 O2 C8 -89.2(5) 6_567 . . 7_665 ? O4 Cu1 O2 C8 -10.2(11) 4_556 . . 7_665 ? O3 Cu1 O2 C8 77.6(5) . . . 7_665 ? N1 Cu1 O2 C8 177.8(5) 8_566 . . 7_665 ? Cu1 Cu1 O2 C8 -5.8(5) 4_556 . . 7_665 ? O4 C9 O3 Cu1 -4.6(9) . . . . ? C4 C9 O3 Cu1 174.9(4) . . . . ? O1 Cu1 O3 C9 17.6(10) 6_567 . . . ? O4 Cu1 O3 C9 85.4(5) 4_556 . . . ? O2 Cu1 O3 C9 -81.3(5) . . . . ? N1 Cu1 O3 C9 178.7(4) 8_566 . . . ? Cu1 Cu1 O3 C9 2.0(4) 4_556 . . . ? O3 C9 O4 Cu1 4.6(9) . . . 4_556 ? C4 C9 O4 Cu1 -174.9(4) . . . 4_556 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5B O1 0.86 2.49 3.096(7) 127.9 3_456 N5 H5B O4 0.86 2.60 3.156(7) 123.3 5_566 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.008 0.008 -0.002 1846 1093 ' ' _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 67.07 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.187 _refine_diff_density_min -0.822 _refine_diff_density_rms 0.157