data_2013215 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2003 _journal_volume 59 _journal_page_first o144 _journal_page_last o146 _publ_section_title ; 3-Nitrophthalic acid: C(4) and R^2^~2~(8) motifs of O---H...O hydrogen bonds generate sheets which are linked by C---H...O hydrogen bonds ; loop_ _publ_author_name 'Glidewell, Christopher' 'Low, John N.' 'Skakle, Janet M. S.' 'Wardell, James L.' _chemical_formula_moiety 'C8 H5 N O6' _chemical_formula_sum 'C8 H5 N O6' _chemical_formula_iupac 'C8 H5 N O6' _chemical_formula_weight 211.13 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' _cell_length_a 9.4972(2) _cell_length_b 6.9014(2) _cell_length_c 12.3077(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.0599(11) _cell_angle_gamma 90.00 _cell_volume 806.17(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _exptl_crystal_density_diffrn 1.740 _diffrn_ambient_temperature 120(2) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.31621(12) 0.42340(17) 0.52082(10) 0.0125(3) Uani d . 1 . . C C2 0.21751(12) 0.46514(16) 0.43625(9) 0.0105(2) Uani d . 1 . . C C3 0.13797(12) 0.63375(17) 0.44588(9) 0.0110(2) Uani d . 1 . . C C4 0.15784(13) 0.76347(17) 0.53133(10) 0.0143(3) Uani d . 1 . . C C5 0.25745(13) 0.72129(19) 0.61288(10) 0.0165(3) Uani d . 1 . . C C6 0.33469(13) 0.55049(19) 0.60876(10) 0.0155(3) Uani d . 1 . . C C11 0.40129(13) 0.24112(18) 0.51580(10) 0.0139(3) Uani d . 1 . . C O11 0.39628(10) 0.13587(13) 0.43643(7) 0.0198(2) Uani d . 1 . . O O12 0.48057(11) 0.20781(14) 0.60382(8) 0.0235(2) Uani d . 1 . . O C21 0.20877(12) 0.33648(16) 0.33651(9) 0.0108(2) Uani d . 1 . . C O21 0.27612(9) 0.37307(12) 0.25687(7) 0.0141(2) Uani d . 1 . . O O22 0.12760(9) 0.18427(12) 0.34762(7) 0.0140(2) Uani d . 1 . . O N31 0.02428(10) 0.67570(14) 0.36443(8) 0.0118(2) Uani d . 1 . . N O31 -0.04206(9) 0.82741(13) 0.37272(8) 0.0179(2) Uani d . 1 . . O O32 -0.00067(10) 0.55423(13) 0.29332(7) 0.0176(2) Uani d . 1 . . O H4 0.1040 0.8793 0.5338 0.017 Uiso calc R 1 . . H H5 0.2730 0.8090 0.6716 0.020 Uiso calc R 1 . . H H6 0.4005 0.5198 0.6661 0.019 Uiso calc R 1 . . H H12 0.5222 0.1013 0.5975 0.035 Uiso calc R 1 . . H H22 0.1448 0.1026 0.2993 0.021 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0132(6) 0.0115(6) 0.0128(6) 0.0007(4) 0.0013(4) 0.0015(4) C2 0.0110(5) 0.0090(5) 0.0117(5) -0.0012(4) 0.0024(4) 0.0010(4) C3 0.0109(5) 0.0101(5) 0.0120(6) -0.0004(4) 0.0012(4) 0.0016(4) C4 0.0142(6) 0.0111(5) 0.0179(6) 0.0010(4) 0.0033(5) -0.0024(5) C5 0.0177(6) 0.0162(6) 0.0155(6) -0.0009(5) 0.0004(5) -0.0045(5) C6 0.0149(6) 0.0182(6) 0.0134(6) -0.0005(5) -0.0011(5) -0.0004(5) C11 0.0135(6) 0.0135(6) 0.0145(6) 0.0010(4) -0.0006(4) 0.0029(4) O11 0.0240(5) 0.0167(5) 0.0183(5) 0.0087(4) -0.0041(4) -0.0031(4) O12 0.0315(5) 0.0191(5) 0.0191(5) 0.0131(4) -0.0083(4) -0.0010(4) C21 0.0117(5) 0.0081(5) 0.0126(6) 0.0033(4) -0.0011(4) 0.0009(4) O21 0.0189(4) 0.0104(4) 0.0132(4) 0.0014(3) 0.0035(3) 0.0007(3) O22 0.0168(4) 0.0094(4) 0.0160(4) -0.0017(3) 0.0030(3) -0.0031(3) N31 0.0122(5) 0.0095(5) 0.0139(5) 0.0003(4) 0.0024(4) 0.0009(4) O31 0.0188(4) 0.0127(4) 0.0221(5) 0.0071(3) -0.0008(4) -0.0006(3) O32 0.0204(5) 0.0145(4) 0.0173(5) 0.0021(3) -0.0050(4) -0.0042(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C11 O11 . 1.2169(16) y C11 O12 . 1.3171(15) y C1 C11 . 1.4977(16) y C21 O21 . 1.2160(15) y C21 O22 . 1.3130(14) y C2 C21 . 1.5148(16) y C1 C6 . 1.3992(17) no C1 C2 . 1.4054(17) no C2 C3 . 1.3947(16) no C3 C4 . 1.3888(17) no C3 N31 . 1.4754(15) no C4 C5 . 1.3853(18) no C4 H4 . 0.95 no C5 C6 . 1.3902(18) no C5 H5 . 0.95 no C6 H6 . 0.95 no O12 H12 . 0.84 no O22 H22 . 0.84 no N31 O31 . 1.2281(13) no N31 O32 . 1.2288(13) no