#------------------------------------------------------------------------------ #$Date: 2020-05-18 17:22:31 +0100 (Mon, 18 May 2020) $ #$Revision: 252130 $ #$URL: svn://www.crystallography.net/cod/cif/3/50/01/3500111.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_3500111 loop_ _publ_author_name 'Thierry Maris' _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8. Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8. ; _journal_name_full 'Personal communication to COD' _journal_year 2020 _chemical_formula_moiety 'C5 H4 N2 O3' _chemical_formula_sum 'C5 H4 N2 O3' _chemical_formula_weight 140.10 _chemical_name_common '3-Pyridinol, 2-Nitro-' _chemical_name_systematic '3-Pyridinol, 2-Nitro-' _space_group_crystal_system orthorhombic _space_group_IT_number 56 _space_group_name_Hall '-P 2ab 2ac' _space_group_name_H-M_alt 'P c c n' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _audit_creation_date 2017-06-02 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337) ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 12.5532(5) _cell_length_b 7.4371(3) _cell_length_c 11.9865(5) _cell_measurement_reflns_used 9229 _cell_measurement_temperature 150 _cell_measurement_theta_max 60.584 _cell_measurement_theta_min 3.063 _cell_volume 1119.05(8) _computing_cell_refinement ; SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_collection ; APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_reduction ; SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'XT (Sheldrick, 2015)' _diffrn_ambient_temperature 150 _diffrn_detector 'CMOS Area detector' _diffrn_detector_area_resol_mean 10.24 _diffrn_detector_type 'Bruker Photon 100 CMOS Detector' _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.973 _diffrn_measurement_device 'k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker Venture Metaljet' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Helios MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type GaK\a _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_unetI/netI 0.0214 _diffrn_reflns_Laue_measured_fraction_full 0.982 _diffrn_reflns_Laue_measured_fraction_max 0.973 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 9685 _diffrn_reflns_point_group_measured_fraction_full 0.982 _diffrn_reflns_point_group_measured_fraction_max 0.973 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 60.552 _diffrn_reflns_theta_min 6.017 _diffrn_source 'Metal Jet' _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _exptl_absorpt_coefficient_mu 0.782 _exptl_absorpt_correction_T_max 0.7519 _exptl_absorpt_correction_T_min 0.6627 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1193 before and 0.0570 after correction. The Ratio of minimum to maximum transmission is 0.8814. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.663 _exptl_crystal_description Block _exptl_crystal_F_000 576 _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector, a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode. ; _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. ; _refine_diff_density_max 0.415 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.125 _refine_ls_extinction_coef 0.069(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2016/6 (Sheldrick 2016)' _refine_ls_goodness_of_fit_ref 1.169 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 115 _refine_ls_number_reflns 1258 _refine_ls_number_restraints 24 _refine_ls_restrained_S_all 1.194 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0502 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0640P)^2^+0.6676P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1237 _refine_ls_wR_factor_ref 0.1257 _refine_special_details ; _shelx_SHELXL_version_number 2016/6 1. Uiso/Uaniso restraints and constraints Uanis(O1) \\sim Ueq, Uanis(O1A) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O2A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002 Uanis(O2) = Uanis(O2A) Uanis(O1) = Uanis(O1A) 2. Others Sof(O1A)=Sof(O2A)=1-FVAR(1) Sof(O2)=Sof(O1)=FVAR(1) ; _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1172 _reflns_number_total 1258 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file t0507.cif _cod_data_source_block t0507 _cod_database_code 3500111 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y+1/2, z' 3 '-x, y+1/2, -z+1/2' 4 'x+1/2, -y, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y-1/2, -z' 7 'x, -y-1/2, z-1/2' 8 '-x-1/2, y, z-1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.37080(10) 0.39084(17) 0.56330(10) 0.0199(3) Uani 1 1 d . . . . . N2 N 0.20815(10) 0.52732(18) 0.51728(10) 0.0201(4) Uani 1 1 d . . . . . O2 O 0.4380(5) 0.3661(9) 0.6304(6) 0.0218(6) Uani 0.396(10) 1 d . U P A 1 O1 O 0.3755(6) 0.3497(10) 0.4630(7) 0.0267(7) Uani 0.396(10) 1 d . U P A 1 O1A O 0.3916(4) 0.3928(7) 0.4635(4) 0.0267(7) Uani 0.604(10) 1 d . U P A 2 O2A O 0.4301(3) 0.3156(7) 0.6350(3) 0.0218(6) Uani 0.604(10) 1 d . U P A 2 O3 O 0.31228(9) 0.44567(17) 0.79525(9) 0.0259(4) Uani 1 1 d . . . . . C1 C 0.27058(11) 0.47489(19) 0.60115(11) 0.0174(4) Uani 1 1 d . . . . . C2 C 0.24602(12) 0.49663(19) 0.71443(11) 0.0183(4) Uani 1 1 d . . . . . C3 C 0.14709(12) 0.5782(2) 0.73698(12) 0.0222(4) Uani 1 1 d . . . . . C4 C 0.08184(12) 0.6318(2) 0.65103(13) 0.0230(4) Uani 1 1 d . . . . . C5 C 0.11588(12) 0.6053(2) 0.54142(12) 0.0223(4) Uani 1 1 d . . . . . H4 H 0.0148(17) 0.685(3) 0.6654(17) 0.028(5) Uiso 1 1 d . . . . . H5 H 0.0782(18) 0.639(3) 0.4783(16) 0.026(5) Uiso 1 1 d . . . . . H3A H 0.1276(16) 0.592(3) 0.8177(17) 0.026(5) Uiso 1 1 d . . . . . H3 H 0.285(2) 0.470(3) 0.861(2) 0.042(6) Uiso 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 N1 0.0187(6) 0.0248(7) 0.0163(6) -0.0007(5) 0.0020(4) -0.0021(5) N2 0.0195(6) 0.0255(7) 0.0153(6) 0.0010(4) -0.0016(4) -0.0044(5) O2 0.0206(8) 0.0231(15) 0.0216(6) 0.0011(11) -0.0019(5) 0.0021(11) O1 0.0300(12) 0.0318(15) 0.0182(6) 0.0006(11) 0.0060(8) 0.0027(11) O1A 0.0300(12) 0.0318(15) 0.0182(6) 0.0006(11) 0.0060(8) 0.0027(11) O2A 0.0206(8) 0.0231(15) 0.0216(6) 0.0011(11) -0.0019(5) 0.0021(11) O3 0.0222(6) 0.0434(7) 0.0121(5) 0.0001(4) -0.0008(4) 0.0052(5) C1 0.0163(7) 0.0212(7) 0.0147(7) -0.0013(5) 0.0008(5) -0.0027(5) C2 0.0180(7) 0.0223(7) 0.0146(6) -0.0001(5) -0.0006(5) -0.0031(6) C3 0.0214(7) 0.0280(8) 0.0171(7) -0.0010(5) 0.0032(5) -0.0003(6) C4 0.0182(7) 0.0265(8) 0.0243(8) 0.0017(6) 0.0016(6) 0.0004(6) C5 0.0191(7) 0.0278(8) 0.0200(7) 0.0037(5) -0.0028(5) -0.0019(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0140 0.0070 '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 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0390 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O2 N1 O1 126.0(5) . . O2 N1 C1 117.8(3) . . O1 N1 C1 116.2(3) . . O1A N1 O2A 122.8(3) . . O1A N1 C1 118.5(2) . . O2A N1 C1 118.7(2) . . C5 N2 C1 118.46(13) . . C2 O3 H3 110.4(16) . . N2 C1 N1 113.15(12) . . N2 C1 C2 124.57(13) . . C2 C1 N1 122.27(12) . . O3 C2 C1 122.30(13) . . O3 C2 C3 122.26(13) . . C1 C2 C3 115.44(13) . . C2 C3 H3A 116.4(12) . . C4 C3 C2 120.42(13) . . C4 C3 H3A 123.2(12) . . C3 C4 C5 118.80(14) . . C3 C4 H4 121.0(12) . . C5 C4 H4 120.2(12) . . N2 C5 C4 122.29(14) . . N2 C5 H5 112.8(13) . . C4 C5 H5 124.9(13) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N1 O2 1.179(7) . N1 O1 1.242(8) . N1 O1A 1.225(5) . N1 O2A 1.267(4) . N1 C1 1.4762(18) . N2 C1 1.3329(18) . N2 C5 1.327(2) . O3 C2 1.3320(17) . O3 H3 0.88(3) . C1 C2 1.4018(19) . C2 C3 1.408(2) . C3 C4 1.375(2) . C3 H3A 1.00(2) . C4 C5 1.396(2) . C4 H4 0.95(2) . C5 H5 0.93(2) . 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 O3 H3 N2 0.88(3) 1.92(3) 2.7418(16) 154(2) 8_656 O3 H3 O1 0.88(3) 2.51(3) 3.179(8) 132(2) 8_656 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 N1 C1 C2 O3 1.2(2) . . . . N1 C1 C2 C3 -179.64(12) . . . . N2 C1 C2 O3 -178.39(14) . . . . N2 C1 C2 C3 0.8(2) . . . . O2 N1 C1 N2 168.3(4) . . . . O2 N1 C1 C2 -11.3(4) . . . . O1 N1 C1 N2 -12.9(4) . . . . O1 N1 C1 C2 167.5(4) . . . . O1A N1 C1 N2 6.9(3) . . . . O1A N1 C1 C2 -172.7(3) . . . . O2A N1 C1 N2 -171.3(3) . . . . O2A N1 C1 C2 9.1(3) . . . . O3 C2 C3 C4 178.82(14) . . . . C1 N2 C5 C4 -0.8(2) . . . . C1 C2 C3 C4 -0.4(2) . . . . C2 C3 C4 C5 -0.6(2) . . . . C3 C4 C5 N2 1.2(3) . . . . C5 N2 C1 N1 -179.82(12) . . . . C5 N2 C1 C2 -0.2(2) . . . . _cod_database_fobs_code 3500111