#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/52/2225295.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_2225295
loop_
_publ_author_name
'Miao, Fang'
'Qin, Bao-Fu'
'Yang, Li-Zhen'
'Yang, Xin-Juan'
'Zhou, Le'
_publ_section_title
;
 (E)-3-[2,5-Dioxo-3-(propan-2-ylidene)pyrrolidin-1-yl]acrylic
 acid
;
_journal_coeditor_code           IS2521
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o634
_journal_paper_doi               10.1107/S1600536810005040
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H11 N O4'
_chemical_formula_moiety         'C10 H11 N O4'
_chemical_formula_sum            'C10 H11 N O4'
_chemical_formula_weight         209.20
_chemical_name_systematic
;
(E)-3-[2,5-Dioxo-3-(propan-2-ylidene)pyrrolidin-1-yl]acrylic acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.009(3)
_cell_angle_beta                 101.247(2)
_cell_angle_gamma                90.410(3)
_cell_formula_units_Z            2
_cell_length_a                   6.5384(14)
_cell_length_b                   7.5309(17)
_cell_length_c                   10.405(2)
_cell_measurement_reflns_used    773
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     501.73(18)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3845
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.9652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0467
_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)+(0.0581P)²+0.0541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1253
_reflns_number_gt                1255
_reflns_number_total             1849
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2521.cif
_cod_data_source_block           I
_cod_original_cell_volume        501.74(19)
_cod_database_code               2225295
_cod_database_fobs_code          2225295
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 O2 1.2795(3) 0.5891(2) 0.92347(15) 0.0617(5) Uani d . 1 . .
O O1 1.5542(3) 0.5091(3) 0.83867(17) 0.0664(5) Uani d . 1 . .
H H1 1.5982 0.4818 0.9142 0.100 Uiso calc R 1 . .
N N1 0.9689(2) 0.7432(2) 0.55825(16) 0.0375(4) Uani d . 1 . .
O O4 0.6865(2) 0.8327(2) 0.64451(17) 0.0611(5) Uani d . 1 . .
O O3 1.2017(2) 0.6881(2) 0.42194(15) 0.0555(5) Uani d . 1 . .
C C4 1.0334(3) 0.7417(3) 0.4361(2) 0.0372(5) Uani d . 1 . .
C C3 1.0819(3) 0.6860(3) 0.6763(2) 0.0403(5) Uani d . 1 . .
H H3 1.0143 0.6904 0.7472 0.048 Uiso calc R 1 . .
C C5 0.8620(3) 0.8155(3) 0.3422(2) 0.0382(5) Uani d . 1 . .
C C8 0.8650(3) 0.8428(3) 0.2160(2) 0.0445(6) Uani d . 1 . .
C C2 1.2744(3) 0.6264(3) 0.6983(2) 0.0437(6) Uani d . 1 . .
H H2 1.3491 0.6184 0.6309 0.052 Uiso calc R 1 . .
C C1 1.3693(3) 0.5730(3) 0.8297(2) 0.0441(6) Uani d . 1 . .
C C6 0.6859(3) 0.8529(3) 0.4118(2) 0.0458(6) Uani d . 1 . .
H H6A 0.6463 0.9765 0.4060 0.055 Uiso calc R 1 . .
H H6B 0.5654 0.7782 0.3743 0.055 Uiso calc R 1 . .
C C7 0.7675(3) 0.8117(3) 0.5505(2) 0.0433(5) Uani d . 1 . .
C C10 0.6796(4) 0.9171(3) 0.1284(2) 0.0580(7) Uani d . 1 . .
H H10A 0.5714 0.9396 0.1773 0.087 Uiso calc R 1 . .
H H10B 0.6294 0.8331 0.0563 0.087 Uiso calc R 1 . .
H H10C 0.7192 1.0262 0.0953 0.087 Uiso calc R 1 . .
C C9 1.0460(4) 0.8041(4) 0.1519(3) 0.0675(8) Uani d . 1 . .
H H9A 1.1076 0.9138 0.1338 0.101 Uiso calc R 1 . .
H H9B 0.9992 0.7347 0.0713 0.101 Uiso calc R 1 . .
H H9C 1.1476 0.7388 0.2093 0.101 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
C1 O1 H1 . . 109.5 ?
C3 N1 C7 . . 120.90(18) ?
C3 N1 C4 . . 127.07(17) ?
C7 N1 C4 . . 112.03(17) ?
O3 C4 N1 . . 122.39(18) ?
O3 C4 C5 . . 130.8(2) ?
N1 C4 C5 . . 106.80(17) ?
C2 C3 N1 . . 127.1(2) ?
C2 C3 H3 . . 116.5 ?
N1 C3 H3 . . 116.5 ?
C8 C5 C4 . . 125.4(2) ?
C8 C5 C6 . . 126.63(19) ?
C4 C5 C6 . . 107.97(18) ?
C5 C8 C9 . . 124.3(2) ?
C5 C8 C10 . . 120.9(2) ?
C9 C8 C10 . . 114.8(2) ?
C3 C2 C1 . . 119.5(2) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
O2 C1 O1 . . 123.3(2) ?
O2 C1 C2 . . 122.4(2) ?
O1 C1 C2 . . 114.3(2) ?
C7 C6 C5 . . 105.09(17) ?
C7 C6 H6A . . 110.7 ?
C5 C6 H6A . . 110.7 ?
C7 C6 H6B . . 110.7 ?
C5 C6 H6B . . 110.7 ?
H6A C6 H6B . . 108.8 ?
O4 C7 N1 . . 122.9(2) ?
O4 C7 C6 . . 129.1(2) ?
N1 C7 C6 . . 107.93(18) ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
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
O2 C1 . 1.234(3) ?
O1 C1 . 1.293(3) ?
O1 H1 . 0.8200 ?
N1 C3 . 1.395(3) ?
N1 C7 . 1.407(3) ?
N1 C4 . 1.415(3) ?
O4 C7 . 1.203(3) ?
O3 C4 . 1.207(2) ?
C4 C5 . 1.469(3) ?
C3 C2 . 1.321(3) ?
C3 H3 . 0.9300 ?
C5 C8 . 1.343(3) ?
C5 C6 . 1.496(3) ?
C8 C9 . 1.491(3) ?
C8 C10 . 1.499(3) ?
C2 C1 . 1.465(3) ?
C2 H2 . 0.9300 ?
C6 C7 . 1.488(3) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
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
O1 H1 O2 2_867 0.82 1.83 2.647(2) 174
C6 H6A O4 2_676 0.97 2.60 3.399(3) 140
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
C3 N1 C4 O3 . . . . -0.1(3) ?
C7 N1 C4 O3 . . . . 179.89(19) ?
C3 N1 C4 C5 . . . . -179.71(17) ?
C7 N1 C4 C5 . . . . 0.3(2) ?
C7 N1 C3 C2 . . . . -176.9(2) ?
C4 N1 C3 C2 . . . . 3.1(3) ?
O3 C4 C5 C8 . . . . -2.1(4) ?
N1 C4 C5 C8 . . . . 177.4(2) ?
O3 C4 C5 C6 . . . . 177.6(2) ?
N1 C4 C5 C6 . . . . -2.9(2) ?
C4 C5 C8 C9 . . . . -0.8(4) ?
C6 C5 C8 C9 . . . . 179.6(2) ?
C4 C5 C8 C10 . . . . 179.3(2) ?
C6 C5 C8 C10 . . . . -0.4(3) ?
N1 C3 C2 C1 . . . . 179.57(19) ?
C3 C2 C1 O2 . . . . -3.5(3) ?
C3 C2 C1 O1 . . . . 177.0(2) ?
C8 C5 C6 C7 . . . . -176.1(2) ?
C4 C5 C6 C7 . . . . 4.3(2) ?
C3 N1 C7 O4 . . . . 3.7(3) ?
C4 N1 C7 O4 . . . . -176.4(2) ?
C3 N1 C7 C6 . . . . -177.54(18) ?
C4 N1 C7 C6 . . . . 2.4(2) ?
C5 C6 C7 O4 . . . . 174.6(2) ?
C5 C6 C7 N1 . . . . -4.1(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744482
