#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/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 R₂²(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_paper_doi               10.1107/S0108270103002555
_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       'φ scans, and ω scans with κ 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/[σ²(Fo²)+(0.0344P)²+0.4307P] where P = (Fo²+2Fc²)/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>2σ(I)
_cod_data_source_file            sk1616.cif
_cod_data_source_block           I
_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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2013215
_cod_database_fobs_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_
_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_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_
_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
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 62265
