#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/79/2017974.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_2017974
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
'Tenorio, Juan C.'
'Ellena, Javier'
'De Simone, Carlos A.'
'Ribeiro, Leandro'
_publ_section_title
;
 4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid: X-ray and
 DFT-calculated structure
;
_journal_coeditor_code           EM3036
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o67
_journal_page_last               o70
_journal_paper_doi               10.1107/S0108270111002265
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H7 N O4'
_chemical_formula_moiety         'C11 H7 N O4'
_chemical_formula_sum            'C11 H7 N O4'
_chemical_formula_weight         217.18
_chemical_melting_point          361.0(10)
_chemical_name_systematic
;
4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3326(5)
_cell_length_b                   9.8832(5)
_cell_length_c                   13.3922(11)
_cell_measurement_reflns_used    3141
_cell_measurement_temperature    294
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.91
_cell_volume                     970.53(11)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.063
_diffrn_reflns_av_sigmaI/netI    0.047
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6051
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.17
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisms
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1278
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.084
_refine_ls_R_factor_gt           0.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0644P)²+0.0425P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.109
_refine_ls_wR_factor_ref         0.128
_reflns_number_gt                895
_reflns_number_total             1278
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            em3036.cif
_cod_data_source_block           I
_cod_database_code               2017974
_cod_database_fobs_code          2017974
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_type_symbol
_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
O O1 0.7660(3) 0.2398(3) 0.97977(17) 0.0591(6) Uani d . 1 . .
O O2 0.5223(3) 0.1942(3) 0.88701(19) 0.0612(7) Uani d . 1 . .
H H2 0.4692 0.2131 0.9391 0.092 Uiso calc R 1 . .
O O3 1.3783(4) 0.0171(3) 0.6183(2) 0.0773(9) Uani d . 1 . .
O O4 0.8918(4) 0.1485(3) 0.4308(2) 0.0784(8) Uani d . 1 . .
N N1 1.1066(3) 0.0912(2) 0.55032(19) 0.0486(6) Uani d . 1 . .
C C1 0.7010(4) 0.2050(3) 0.9006(3) 0.0482(8) Uani d . 1 . .
C C2 0.8062(4) 0.1723(3) 0.8095(2) 0.0435(7) Uani d . 1 . .
C C3 0.7299(4) 0.0990(3) 0.7323(3) 0.0515(8) Uani d . 1 . .
H H3 0.6100 0.0691 0.7376 0.062 Uiso calc R 1 . .
C C4 0.8283(4) 0.0696(3) 0.6478(3) 0.0513(8) Uani d . 1 . .
H H4 0.7765 0.0187 0.5968 0.062 Uiso calc R 1 . .
C C5 1.0061(4) 0.1167(3) 0.6394(2) 0.0465(7) Uani d . 1 . .
C C6 1.0854(4) 0.1896(3) 0.7166(3) 0.0505(8) Uani d . 1 . .
H H6 1.2047 0.2205 0.7108 0.061 Uiso calc R 1 . .
C C7 0.9863(4) 0.2159(3) 0.8017(3) 0.0494(8) Uani d . 1 . .
H H7 1.0398 0.2630 0.8542 0.059 Uiso calc R 1 . .
C C8 1.0436(5) 0.1128(3) 0.4524(3) 0.0565(9) Uani d . 1 . .
C C9 1.2005(6) 0.0837(3) 0.3871(3) 0.0685(11) Uani d . 1 . .
H H9 1.1991 0.0882 0.3177 0.082 Uiso calc R 1 . .
C C10 1.3412(6) 0.0508(4) 0.4410(4) 0.0715(11) Uani d . 1 . .
H H10 1.4567 0.0306 0.4165 0.086 Uiso calc R 1 . .
C C11 1.2885(5) 0.0505(3) 0.5466(3) 0.0559(8) Uani d . 1 . .
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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O2 H2 . . 109.5 ?
C11 N1 C8 . . 109.0(3) ?
C11 N1 C5 . . 125.2(3) ?
C8 N1 C5 . . 125.7(3) ?
O1 C1 O2 . . 122.1(3) ?
O1 C1 C2 . . 125.3(3) ?
O2 C1 C2 . . 112.6(3) ?
C3 C2 C7 . . 119.4(3) ?
C3 C2 C1 . . 121.4(3) ?
C7 C2 C1 . . 119.3(3) ?
C4 C3 C2 . . 121.0(3) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C5 . . 119.3(3) ?
C3 C4 H4 . . 120.4 ?
C5 C4 H4 . . 120.4 ?
C6 C5 C4 . . 120.5(3) ?
C6 C5 N1 . . 119.9(3) ?
C4 C5 N1 . . 119.6(3) ?
C7 C6 C5 . . 119.6(3) ?
C7 C6 H6 . . 120.2 ?
C5 C6 H6 . . 120.2 ?
C6 C7 C2 . . 120.3(3) ?
C6 C7 H7 . . 119.9 ?
C2 C7 H7 . . 119.9 ?
O4 C8 N1 . . 124.9(3) ?
O4 C8 C9 . . 129.6(4) ?
N1 C8 C9 . . 105.5(3) ?
C10 C9 C8 . . 109.8(4) ?
C10 C9 H9 . . 125.1 ?
C8 C9 H9 . . 125.1 ?
C9 C10 C11 . . 109.1(4) ?
C9 C10 H10 . . 125.4 ?
C11 C10 H10 . . 125.4 ?
O3 C11 N1 . . 124.8(3) ?
O3 C11 C10 . . 128.5(4) ?
N1 C11 C10 . . 106.6(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
O1 C1 . 1.212(4) ?
O2 C1 . 1.327(4) ?
O2 H2 . 0.8200 ?
O3 C11 . 1.210(5) ?
O4 C8 . 1.202(4) ?
N1 C11 . 1.394(4) ?
N1 C8 . 1.407(4) ?
N1 C5 . 1.424(4) ?
C1 C2 . 1.480(5) ?
C2 C3 . 1.381(4) ?
C2 C7 . 1.392(4) ?
C3 C4 . 1.373(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.389(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.388(4) ?
C6 C7 . 1.377(4) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.474(6) ?
C9 C10 . 1.301(6) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.466(6) ?
C10 H10 . 0.9300 ?
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
O2 H2 O1 3_457 0.82 1.90 2.672(3) 156.0
C3 H3 O3 1_455 0.93 2.39 3.103(4) 133.6
C6 H6 O4 3_556 0.93 2.68 3.392(4) 134.4
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 161.9(3) ?
O2 C1 C2 C3 . . . . -19.1(4) ?
O1 C1 C2 C7 . . . . -17.8(5) ?
O2 C1 C2 C7 . . . . 161.2(3) ?
C7 C2 C3 C4 . . . . -0.6(5) ?
C1 C2 C3 C4 . . . . 179.7(3) ?
C2 C3 C4 C5 . . . . -1.2(5) ?
C3 C4 C5 C6 . . . . 1.7(5) ?
C3 C4 C5 N1 . . . . -177.5(3) ?
C11 N1 C5 C6 . . . . 43.8(4) ?
C8 N1 C5 C6 . . . . -131.0(3) ?
C11 N1 C5 C4 . . . . -137.0(3) ?
C8 N1 C5 C4 . . . . 48.2(4) ?
C4 C5 C6 C7 . . . . -0.4(5) ?
N1 C5 C6 C7 . . . . 178.8(3) ?
C5 C6 C7 C2 . . . . -1.4(5) ?
C3 C2 C7 C6 . . . . 1.9(5) ?
C1 C2 C7 C6 . . . . -178.4(3) ?
C11 N1 C8 O4 . . . . 179.9(3) ?
C5 N1 C8 O4 . . . . -4.6(5) ?
C11 N1 C8 C9 . . . . -0.5(3) ?
C5 N1 C8 C9 . . . . 175.0(3) ?
O4 C8 C9 C10 . . . . 178.6(4) ?
N1 C8 C9 C10 . . . . -0.9(4) ?
C8 C9 C10 C11 . . . . 1.9(4) ?
C8 N1 C11 O3 . . . . -175.8(3) ?
C5 N1 C11 O3 . . . . 8.7(5) ?
C8 N1 C11 C10 . . . . 1.6(3) ?
C5 N1 C11 C10 . . . . -174.0(3) ?
C9 C10 C11 O3 . . . . 175.0(4) ?
C9 C10 C11 N1 . . . . -2.2(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 78416
