#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/51/2225184.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_2225184
loop_
_publ_author_name
'Kasunič, Marta'
'Verček, Bojan'
'Mušič, Irena'
'Golobič, Amalija'
_publ_section_title
;
 3-Benzamido-1-benzoyl-1H-pyrrol-2(5H)-one
;
_journal_coeditor_code           BT5197
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o687
_journal_paper_doi               10.1107/S1600536810006483
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H14 N2 O3'
_chemical_formula_moiety         'C18 H14 N2 O3'
_chemical_formula_sum            'C18 H14 N2 O3'
_chemical_formula_weight         306.31
_chemical_name_systematic
;
3-Benzamido-1-benzoyl-1H-pyrrol-2(5H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 95.908(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.966(2)
_cell_length_b                   5.8891(7)
_cell_length_c                   12.3290(10)
_cell_measurement_reflns_used    75
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15.25
_cell_measurement_theta_min      7.99
_cell_volume                     1514.2(3)
_computing_cell_refinement
'the XRAY76 System (Stewart et al.,  1976)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD-4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'ω/2θ scans [width (0.85 + 0.3tanθ)]'
_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  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13450
_diffrn_reflns_theta_full        27.96
_diffrn_reflns_theta_max         27.96
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        1.11
_diffrn_standards_interval_time  333.3
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.182
_refine_ls_extinction_coef       0.029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELX97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0676P)²+0.1617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1318
_reflns_number_gt                2119
_reflns_number_total             3648
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5197.cif
_cod_data_source_block           I
_cod_database_code               2225184
_cod_database_fobs_code          2225184
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
N N1 0.80491(6) 0.1771(2) 0.90089(10) 0.0492(3) Uani d . 1 . .
N N2 0.69375(7) 0.6347(2) 0.88815(11) 0.0554(4) Uani d . 1 . .
H H2 0.6985 0.6820 0.8235 0.066 Uiso calc R 1 . .
O O1 0.77372(6) 0.4192(2) 0.75402(9) 0.0632(4) Uani d . 1 . .
O O2 0.85617(8) -0.1579(2) 0.90309(12) 0.0846(5) Uani d . 1 . .
O O3 0.64221(7) 0.6962(3) 1.03607(10) 0.0784(4) Uani d . 1 . .
C C1 0.78338(8) 0.1439(3) 1.00943(12) 0.0534(4) Uani d . 1 . .
H H1A 0.8190 0.1548 1.0660 0.064 Uiso calc R 1 . .
H H1B 0.7627 -0.0024 1.0147 0.064 Uiso calc R 1 . .
C C2 0.73736(8) 0.3319(3) 1.01751(13) 0.0550(4) Uani d . 1 . .
H H2A 0.7162 0.3627 1.0785 0.066 Uiso calc R 1 . .
C C3 0.73060(7) 0.4501(3) 0.92579(12) 0.0483(4) Uani d . 1 . .
C C4 0.77164(7) 0.3562(3) 0.84693(12) 0.0472(4) Uani d . 1 . .
C C5 0.84667(8) 0.0250(3) 0.85911(13) 0.0534(4) Uani d . 1 . .
C C6 0.88045(7) 0.0966(3) 0.76467(12) 0.0453(4) Uani d . 1 . .
C C7 0.88460(8) -0.0552(3) 0.67966(14) 0.0549(4) Uani d . 1 . .
H H7 0.8640 -0.1950 0.6800 0.066 Uiso calc R 1 . .
C C8 0.91946(9) 0.0018(3) 0.59465(14) 0.0634(5) Uani d . 1 . .
H H8 0.9210 -0.0975 0.5363 0.076 Uiso calc R 1 . .
C C9 0.95206(9) 0.2049(3) 0.59581(15) 0.0619(5) Uani d . 1 . .
H H9 0.9763 0.2408 0.5391 0.074 Uiso calc R 1 . .
C C10 0.94882(8) 0.3549(3) 0.68073(14) 0.0555(4) Uani d . 1 . .
H H10 0.9712 0.4913 0.6817 0.067 Uiso calc R 1 . .
C C11 0.91240(7) 0.3029(3) 0.76453(12) 0.0487(4) Uani d . 1 . .
H H11 0.9093 0.4061 0.8208 0.058 Uiso calc R 1 . .
C C12 0.65088(8) 0.7482(3) 0.94360(13) 0.0528(4) Uani d . 1 . .
C C13 0.61696(8) 0.9416(3) 0.88463(13) 0.0512(4) Uani d . 1 . .
C C14 0.57527(10) 1.0680(4) 0.93989(16) 0.0712(6) Uani d . 1 . .
H H14 0.5678 1.0268 1.0103 0.085 Uiso calc R 1 . .
C C15 0.54448(12) 1.2550(4) 0.8915(2) 0.0884(7) Uani d . 1 . .
H H15 0.5166 1.3397 0.9294 0.106 Uiso calc R 1 . .
C C16 0.55488(11) 1.3153(4) 0.7884(2) 0.0860(7) Uani d . 1 . .
H H16 0.5347 1.4425 0.7561 0.103 Uiso calc R 1 . .
C C17 0.59485(12) 1.1893(5) 0.7325(2) 0.0956(8) Uani d . 1 . .
H H17 0.6015 1.2299 0.6616 0.115 Uiso calc R 1 . .
C C18 0.62549(10) 1.0025(4) 0.77981(16) 0.0770(6) Uani d . 1 . .
H H18 0.6523 0.9165 0.7403 0.092 Uiso calc R 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C4 . . 127.91(13) ?
C5 N1 C1 . . 121.13(13) ?
C4 N1 C1 . . 110.46(13) ?
C12 N2 C3 . . 126.31(14) ?
C12 N2 H2 . . 116.8 ?
C3 N2 H2 . . 116.8 ?
N1 C1 C2 . . 103.04(13) ?
N1 C1 H1A . . 111.2 ?
C2 C1 H1A . . 111.2 ?
N1 C1 H1B . . 111.2 ?
C2 C1 H1B . . 111.2 ?
H1A C1 H1B . . 109.1 ?
C3 C2 C1 . . 110.47(14) ?
C3 C2 H2A . . 124.8 ?
C1 C2 H2A . . 124.8 ?
C2 C3 N2 . . 134.92(15) ?
C2 C3 C4 . . 110.40(15) ?
N2 C3 C4 . . 114.67(13) ?
O1 C4 N1 . . 128.21(15) ?
O1 C4 C3 . . 126.27(15) ?
N1 C4 C3 . . 105.48(13) ?
O2 C5 N1 . . 119.19(16) ?
O2 C5 C6 . . 122.21(16) ?
N1 C5 C6 . . 118.54(14) ?
C11 C6 C7 . . 119.70(15) ?
C11 C6 C5 . . 121.26(14) ?
C7 C6 C5 . . 118.79(15) ?
C8 C7 C6 . . 119.78(17) ?
C8 C7 H7 . . 120.1 ?
C6 C7 H7 . . 120.1 ?
C9 C8 C7 . . 120.31(16) ?
C9 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C8 C9 C10 . . 120.13(17) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
C9 C10 C11 . . 120.07(17) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C10 C11 C6 . . 119.96(15) ?
C10 C11 H11 . . 120.0 ?
C6 C11 H11 . . 120.0 ?
O3 C12 N2 . . 121.29(17) ?
O3 C12 C13 . . 122.77(15) ?
N2 C12 C13 . . 115.92(14) ?
C18 C13 C14 . . 118.38(18) ?
C18 C13 C12 . . 123.87(16) ?
C14 C13 C12 . . 117.74(16) ?
C15 C14 C13 . . 120.6(2) ?
C15 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C16 C15 C14 . . 120.0(2) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C15 C16 C17 . . 119.9(2) ?
C15 C16 H16 . . 120.0 ?
C17 C16 H16 . . 120.0 ?
C16 C17 C18 . . 120.5(2) ?
C16 C17 H17 . . 119.7 ?
C18 C17 H17 . . 119.7 ?
C13 C18 C17 . . 120.6(2) ?
C13 C18 H18 . . 119.7 ?
C17 C18 H18 . . 119.7 ?
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
N1 C5 . 1.388(2) ?
N1 C4 . 1.395(2) ?
N1 C1 . 1.4687(19) ?
N2 C12 . 1.360(2) ?
N2 C3 . 1.385(2) ?
N2 H2 . 0.8600 ?
O1 C4 . 1.2091(18) ?
O2 C5 . 1.213(2) ?
O3 C12 . 1.2121(19) ?
C1 C2 . 1.479(3) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C3 . 1.323(2) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.471(2) ?
C5 C6 . 1.485(2) ?
C6 C11 . 1.387(2) ?
C6 C7 . 1.387(2) ?
C7 C8 . 1.379(2) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.377(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.377(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.381(2) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C13 . 1.492(2) ?
C13 C18 . 1.370(2) ?
C13 C14 . 1.380(2) ?
C14 C15 . 1.381(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.358(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.359(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.373(3) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
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
C5 N1 C1 C2 . . . . -176.46(15) ?
C4 N1 C1 C2 . . . . -3.92(17) ?
N1 C1 C2 C3 . . . . 2.68(19) ?
C1 C2 C3 N2 . . . . 178.14(18) ?
C1 C2 C3 C4 . . . . -0.6(2) ?
C12 N2 C3 C2 . . . . -0.5(3) ?
C12 N2 C3 C4 . . . . 178.20(15) ?
C5 N1 C4 O1 . . . . -2.2(3) ?
C1 N1 C4 O1 . . . . -174.11(17) ?
C5 N1 C4 C3 . . . . 175.56(15) ?
C1 N1 C4 C3 . . . . 3.67(17) ?
C2 C3 C4 O1 . . . . 175.90(17) ?
N2 C3 C4 O1 . . . . -3.1(3) ?
C2 C3 C4 N1 . . . . -1.93(19) ?
N2 C3 C4 N1 . . . . 179.08(13) ?
C4 N1 C5 O2 . . . . -157.39(17) ?
C1 N1 C5 O2 . . . . 13.7(2) ?
C4 N1 C5 C6 . . . . 25.3(2) ?
C1 N1 C5 C6 . . . . -163.60(14) ?
O2 C5 C6 C11 . . . . -127.91(19) ?
N1 C5 C6 C11 . . . . 49.3(2) ?
O2 C5 C6 C7 . . . . 46.4(2) ?
N1 C5 C6 C7 . . . . -136.36(16) ?
C11 C6 C7 C8 . . . . -1.2(2) ?
C5 C6 C7 C8 . . . . -175.60(15) ?
C6 C7 C8 C9 . . . . 2.4(3) ?
C7 C8 C9 C10 . . . . -1.5(3) ?
C8 C9 C10 C11 . . . . -0.6(3) ?
C9 C10 C11 C6 . . . . 1.8(2) ?
C7 C6 C11 C10 . . . . -0.9(2) ?
C5 C6 C11 C10 . . . . 173.38(15) ?
C3 N2 C12 O3 . . . . 1.6(3) ?
C3 N2 C12 C13 . . . . -179.80(15) ?
O3 C12 C13 C18 . . . . -179.38(19) ?
N2 C12 C13 C18 . . . . 2.0(3) ?
O3 C12 C13 C14 . . . . 1.6(3) ?
N2 C12 C13 C14 . . . . -177.04(16) ?
C18 C13 C14 C15 . . . . -1.9(3) ?
C12 C13 C14 C15 . . . . 177.23(18) ?
C13 C14 C15 C16 . . . . 0.4(3) ?
C14 C15 C16 C17 . . . . 1.0(4) ?
C15 C16 C17 C18 . . . . -0.7(4) ?
C14 C13 C18 C17 . . . . 2.1(3) ?
C12 C13 C18 C17 . . . . -176.9(2) ?
C16 C17 C18 C13 . . . . -0.9(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9220141
