#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/28/2202820.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_2202820
loop_
_publ_author_name
Vasu
'K. A. Nirmala'
'Deepak Chopra'
'M. Vishwas'
_publ_section_title
;
 Ethyl 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1549
_journal_page_last               o1550
_journal_paper_doi               10.1107/S1600536803020701
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C13 H11 N O4'
_chemical_formula_moiety         'C13 H11 N O4'
_chemical_formula_sum            'C13 H11 N O4'
_chemical_formula_weight         245.23
_chemical_name_systematic
;
Ethyl 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoate
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 96.364(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.028(6)
_cell_length_b                   7.358(4)
_cell_length_c                   13.561(7)
_cell_measurement_reflns_used    775
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5
_cell_measurement_theta_min      2.2
_cell_volume                     1192.8(11)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin, 1993)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare, 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0134
_diffrn_reflns_av_sigmaI/netI    0.0133
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8371
_diffrn_reflns_reduction_process
;
 ?
;
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.9031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.314
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0441
_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)+(0.0933P)²+0.1715P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1380
_reflns_number_gt                1965
_reflns_number_total             2328
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6303.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_cell_volume        1192.9(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2202820
_cod_database_fobs_code          2202820
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
x,1/2-y,1/2+z
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
O1 0.38443(10) 0.3350(2) 0.49702(10) 0.0737(4) Uani d . 1 . . O
O2 0.51187(12) -0.0551(3) 0.74371(13) 0.1025(6) Uani d . 1 . . O
O3 -0.11005(9) 0.0763(2) 0.65990(9) 0.0694(4) Uani d . 1 . . O
O4 -0.04247(8) 0.10226(16) 0.82013(8) 0.0541(3) Uani d . 1 . . O
N1 0.41506(9) 0.12811(15) 0.62585(8) 0.0403(3) Uani d . 1 . . N
C1 0.44679(12) 0.2432(2) 0.55179(10) 0.0486(4) Uani d . 1 . . C
C2 0.56988(13) 0.2254(2) 0.55475(13) 0.0594(4) Uani d . 1 . . C
C3 0.60637(14) 0.1140(3) 0.62521(14) 0.0605(5) Uani d . 1 . . C
C4 0.51060(13) 0.0471(2) 0.67553(12) 0.0563(4) Uani d . 1 . . C
C5 0.30424(11) 0.11369(17) 0.65244(10) 0.0379(3) Uani d . 1 . . C
C6 0.21556(12) 0.1047(2) 0.57787(11) 0.0451(3) Uani d . 1 . . C
C7 0.10794(12) 0.0986(2) 0.60345(11) 0.0472(4) Uani d . 1 . . C
C8 0.08690(11) 0.09822(18) 0.70209(11) 0.0425(3) Uani d . 1 . . C
C9 0.17659(12) 0.1051(2) 0.77632(11) 0.0458(4) Uani d . 1 . . C
C10 0.28494(12) 0.1133(2) 0.75209(11) 0.0444(3) Uani d . 1 . . C
C11 -0.03175(12) 0.0909(2) 0.72345(12) 0.0469(4) Uani d . 1 . . C
C12 -0.15584(12) 0.0953(2) 0.84737(13) 0.0535(4) Uani d . 1 . . C
C13 -0.14843(16) 0.0956(3) 0.95780(15) 0.0651(5) Uani d . 1 . . C
H2 0.6094(16) 0.294(3) 0.5083(14) 0.072(5) Uiso d . 1 . . H
H3 0.680(2) 0.076(3) 0.6454(17) 0.089(7) Uiso d . 1 . . H
H6 0.2281(13) 0.101(2) 0.5105(13) 0.048(4) Uiso d . 1 . . H
H7 0.0459(16) 0.099(2) 0.5507(14) 0.059(5) Uiso d . 1 . . H
H9 0.1658(15) 0.103(2) 0.8425(14) 0.062(5) Uiso d . 1 . . H
H10 0.3469(15) 0.121(2) 0.8059(13) 0.057(5) Uiso d . 1 . . H
H12A -0.1893(15) -0.017(3) 0.8187(13) 0.063(5) Uiso d . 1 . . H
H12B -0.1959(17) 0.203(3) 0.8166(14) 0.073(5) Uiso d . 1 . . H
H13A -0.1037(18) -0.006(3) 0.9867(15) 0.081(6) Uiso d . 1 . . H
H13B -0.222(2) 0.082(3) 0.9782(16) 0.085(6) Uiso d . 1 . . H
H13C -0.1213(19) 0.208(4) 0.9864(17) 0.091(7) Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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
C4 N1 C1 109.20(12)
C4 N1 C5 126.06(12)
C1 N1 C5 124.39(11)
C11 O4 C12 116.32(12)
C6 C5 C10 120.55(13)
C6 C5 N1 119.01(12)
C10 C5 N1 120.42(12)
C6 C7 C8 121.29(13)
C6 C7 H7 118.6(11)
C8 C7 H7 120.0(11)
C7 C8 C9 119.14(13)
C7 C8 C11 117.95(13)
C9 C8 C11 122.91(14)
O3 C11 O4 123.62(14)
O3 C11 C8 123.54(15)
O4 C11 C8 112.84(12)
C9 C10 C5 119.55(13)
C9 C10 H10 118.9(10)
C5 C10 H10 121.6(10)
C10 C9 C8 120.38(14)
C10 C9 H9 118.1(11)
C8 C9 H9 121.5(11)
C7 C6 C5 119.08(13)
C7 C6 H6 120.0(10)
C5 C6 H6 121.0(10)
O1 C1 N1 125.61(13)
O1 C1 C2 128.23(14)
N1 C1 C2 106.15(13)
C2 C3 C4 109.34(15)
C2 C3 H3 129.4(14)
C4 C3 H3 121.2(14)
O2 C4 N1 125.60(15)
O2 C4 C3 128.46(15)
N1 C4 C3 105.94(14)
O4 C12 C13 107.59(13)
O4 C12 H12A 106.5(10)
C13 C12 H12A 112.0(10)
O4 C12 H12B 106.8(11)
C13 C12 H12B 113.1(11)
H12A C12 H12B 110.4(16)
C3 C2 C1 109.32(14)
C3 C2 H2 130.9(12)
C1 C2 H2 119.8(12)
C12 C13 H13A 111.8(12)
C12 C13 H13C 112.9(14)
H13A C13 H13C 110.4(19)
C12 C13 H13B 109.5(13)
H13A C13 H13B 106.7(17)
H13C C13 H13B 105.1(18)
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 C4 . 1.3994(19) ?
N1 C1 . 1.3989(18) ?
N1 C5 . 1.4230(17) ?
O4 C11 . 1.334(2) ?
O4 C12 . 1.4528(18) ?
O3 C11 . 1.209(2) ?
O2 C4 . 1.191(2) ?
O1 C1 . 1.2030(19) ?
C5 C6 . 1.388(2) ?
C5 C10 . 1.396(2) ?
C7 C6 . 1.377(2) ?
C7 C8 . 1.389(2) ?
C7 H7 . 0.974(19) ?
C8 C9 . 1.392(2) ?
C8 C11 . 1.488(2) ?
C10 C9 . 1.380(2) ?
C10 H10 . 0.986(18) ?
C9 H9 . 0.921(19) ?
C6 H6 . 0.943(17) ?
C1 C2 . 1.482(2) ?
C3 C2 . 1.298(3) ?
C3 C4 . 1.486(2) ?
C3 H3 . 0.94(2) ?
C12 C13 . 1.490(3) ?
C12 H12A . 0.98(2) ?
C12 H12B . 1.00(2) ?
C2 H2 . 0.97(2) ?
C13 H13A . 0.98(2) ?
C13 H13C . 0.96(3) ?
C13 H13B . 0.97(2) ?
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
C3 H3 O3 1_655 0.94(2) 2.51(2) 3.402(3) 158(2) yes
C10 H10 O1 4_555 0.98(2) 2.61(2) 3.426(3) 141.0(10) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 252600
