#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/32/2013215.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2013215 loop_ _publ_author_name 'Glidewell, Christopher' 'Low, John N.' 'Skakle, Janet M. S.' 'Wardell, James L.' _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 ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o144 _journal_page_last o146 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C8 H5 N O6' _chemical_formula_moiety 'C8 H5 N O6' _chemical_formula_sum 'C8 H5 N O6' _chemical_formula_weight 211.13 _chemical_name_systematic ; 3-Nitrophthalic acid ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 92.0599(11) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.4972(2) _cell_length_b 6.9014(2) _cell_length_c 12.3077(3) _cell_measurement_reflns_used 1827 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.46 _cell_measurement_theta_min 3.38 _cell_volume 806.17(3) _computing_cell_refinement 'DENZO--SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO--SMN _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 9456 _diffrn_reflns_theta_full 27.46 _diffrn_reflns_theta_max 27.46 _diffrn_reflns_theta_min 3.38 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 0.154 _exptl_absorpt_correction_T_max 0.972 _exptl_absorpt_correction_T_min 0.945 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.740 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 432 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.316 _refine_diff_density_min -0.325 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 138 _refine_ls_number_reflns 1827 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.0381 _refine_ls_R_factor_gt 0.0338 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean <0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0344P)^2^+0.4307P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0837 _refine_ls_wR_factor_ref 0.0867 _reflns_number_gt 1641 _reflns_number_total 1827 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1616.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2013215 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' 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 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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 C1 C6 120.41(11) y C6 C1 C11 120.37(11) no C2 C1 C11 119.22(11) no C1 C2 C3 117.19(11) y C3 C2 C21 122.95(10) no C1 C2 C21 119.71(10) no C2 C3 C4 122.89(11) y C4 C3 N31 117.66(10) no C2 C3 N31 119.43(10) no C5 C4 C3 118.93(11) no C5 C4 H4 120.5 no C3 C4 H4 120.5 no C4 C5 C6 119.95(11) no C4 C5 H5 120.0 no C6 C5 H5 120.0 no C5 C6 C1 120.53(12) no C5 C6 H6 119.7 no C1 C6 H6 119.7 no O11 C11 O12 124.12(11) no O11 C11 C1 121.93(11) no O12 C11 C1 113.95(10) no C11 O12 H12 109.5 no O21 C21 O22 125.30(11) no O21 C21 C2 121.09(10) no O22 C21 C2 113.57(10) no C21 O22 H22 109.5 no O31 N31 O32 123.67(10) no O31 N31 C3 118.42(10) no O32 N31 C3 117.89(9) no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O12 H12 O11 3_656 0.84 1.86 2.6983(13) 172 y O22 H22 O21 4_656 0.84 1.89 2.6809(12) 155 y C4 H4 O31 3_576 0.95 2.41 3.2663(15) 150 y 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_publ_flag C6 C1 C2 C3 -1.65(17) no C11 C1 C2 C3 178.28(10) no C6 C1 C2 C21 174.06(10) no C11 C1 C2 C21 -6.02(16) no C1 C2 C3 C4 3.38(17) no C21 C2 C3 C4 -172.17(11) no C1 C2 C3 N31 -174.63(10) no C21 C2 C3 N31 9.81(16) no C2 C3 C4 C5 -2.31(18) no N31 C3 C4 C5 175.74(10) no C3 C4 C5 C6 -0.56(18) no C4 C5 C6 C1 2.21(19) no C2 C1 C6 C5 -1.07(18) no C11 C1 C6 C5 179.01(11) no C6 C1 C11 O11 -173.77(12) no C2 C1 C11 O11 6.30(18) y C6 C1 C11 O12 5.97(17) no C2 C1 C11 O12 -173.96(11) no C3 C2 C21 O21 83.34(15) no C1 C2 C21 O21 -92.11(14) y C3 C2 C21 O22 -98.93(13) no C1 C2 C21 O22 85.62(13) no C4 C3 N31 O31 3.79(16) no C2 C3 N31 O31 -178.09(10) no C4 C3 N31 O32 -174.64(10) no C2 C3 N31 O32 3.48(15) y _cod_database_fobs_code 2013215 _journal_paper_doi 10.1107/S0108270103002555