π-Stacked hydrogen-bonded dimers in 2-(2-nitrophenylaminocarbonyl)benzoic acid, and hydrogen-bonded sheets in orthorhombic and monoclinic polymorphs of 2-(4-nitrophenylaminocarbonyl)benzoic acid
Glidewell, Christopher; Low, John N.; Skakle, Janet M. S.; Wardell, James L.; Acta Crystallographica Section C 60 (2004) o120–o124; doi:10.1107/S0108270103027914

data_2013807
_publ_section_title
;
 \p-Stacked hydrogen-bonded dimers in
 2-(2-nitrophenylaminocarbonyl)benzoic acid, and hydrogen-bonded sheets
 in orthorhombic and monoclinic polymorphs of
 2-(4-nitrophenylaminocarbonyl)benzoic acid
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o120
_journal_page_last               o124
_journal_paper_doi               10.1107/S0108270103027914
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C14 H10 N2 O5'
_chemical_formula_moiety         'C14 H10 N2 O5'
_chemical_formula_sum            'C14 H10 N2 O5'
_chemical_formula_weight         286.24
_chemical_name_common
;
N-(4-Nitrophenyl)benzamide-2-carboxylic acid, orthorhombic polymorph
;
_chemical_name_systematic
;
2-(4-nitrophenylaminocarbonyl)benzoic acid
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9188(2)
_cell_length_b                   12.6896(6)
_cell_length_c                   27.7029(16)
_cell_measurement_reflns_used    1820
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.21
_cell_volume                     1377.61(12)
_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, 2003)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_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  0.052
_diffrn_reflns_av_sigmaI/netI    0.069
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            4875
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.21
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1820
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.087
_refine_ls_R_factor_gt           0.055
_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^)+(0.0583P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.114
_refine_ls_wR_factor_ref         0.123
_reflns_number_gt                1237
_reflns_number_total             1820
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gg1204.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
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_cod_database_code               2013807
_cod_database_fobs_code          2013807