#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/92/2239207.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_2239207
loop_
_publ_author_name
'Pearson, Wayne H.'
'Lin, Shirley'
'Isaacs, Lyle'
_publ_section_title
;
 2,5-Dioxopyrrolidin-1-yl 2-methylprop-2-enoate
;
_journal_coeditor_code           ZQ2217
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o446
_journal_paper_doi               10.1107/S1600536814005170
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C8 H9 N O4'
_chemical_formula_moiety         'C8 H9 N O4'
_chemical_formula_sum            'C8 H9 N O4'
_chemical_formula_weight         183.16
_chemical_name_systematic
;
2,5-Dioxopyrrolidin-1-yl 2-methylprop-2-enoate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                 102.522(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6137(8)
_cell_length_b                   10.9317(9)
_cell_length_c                   8.4911(7)
_cell_measurement_reflns_used    8309
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.31
_cell_measurement_theta_min      2.17
_cell_volume                     871.14(12)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII DUO'
_diffrn_measurement_method       'combination of omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source
'a micro-focus source with X-ray optics for beam focussing and collimation'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20817
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2004)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      1.337(2)
_exptl_crystal_density_method    flotation
_exptl_crystal_description       parallelpiped
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0362
_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)+(0.0278P)²+0.4720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0848
_reflns_number_gt                1353
_reflns_number_total             1595
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zq2217sup1.cif
_cod_data_source_block           I
_cod_database_code               2239207
_cod_database_fobs_code          2239207
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_symmetry_multiplicity
C C1 0.82074(17) 0.05447(15) 0.09507(19) 0.0323(4) Uani d . 1 1
H H1A 0.8376 0.0287 -0.0110 0.039 Uiso calc R 1 1
H H1B 0.7895 -0.0176 0.1490 0.039 Uiso calc R 1 1
C C2 0.95609(18) 0.10915(15) 0.19895(19) 0.0326(4) Uani d . 1 1
H H2A 0.9894 0.0594 0.2973 0.039 Uiso calc R 1 1
H H2B 1.0329 0.1126 0.1380 0.039 Uiso calc R 1 1
C C3 0.91646(17) 0.23566(15) 0.24251(18) 0.0301(4) Uani d . 1 1
C C4 0.71008(17) 0.15357(14) 0.07441(18) 0.0283(4) Uani d . 1 1
C C5 0.72829(16) 0.44523(14) 0.06764(17) 0.0261(3) Uani d . 1 1
C C6 0.66346(16) 0.56484(14) 0.09024(18) 0.0270(4) Uani d . 1 1
C C7 0.6865(2) 0.66054(16) -0.0276(2) 0.0420(4) Uani d . 1 1
H H7A 0.6435 0.7377 -0.0037 0.063 Uiso calc R 1 1
H H7B 0.6422 0.6342 -0.1373 0.063 Uiso calc R 1 1
H H7C 0.7890 0.6723 -0.0188 0.063 Uiso calc R 1 1
C C8 0.59118(17) 0.58160(15) 0.20439(19) 0.0324(4) Uani d . 1 1
H H8A 0.5800 0.5160 0.2740 0.039 Uiso calc R 1 1
H H8B 0.5504 0.6592 0.2168 0.039 Uiso calc R 1 1
N N1 0.77548(14) 0.25062(11) 0.16597(15) 0.0289(3) Uani d . 1 1
O O1 0.98688(13) 0.31280(11) 0.32386(15) 0.0441(3) Uani d . 1 1
O O2 0.58963(13) 0.15423(11) -0.00275(15) 0.0408(3) Uani d . 1 1
O O3 0.70452(12) 0.35922(9) 0.17939(13) 0.0319(3) Uani d . 1 1
O O4 0.79410(13) 0.42090(11) -0.03174(14) 0.0402(3) Uani d . 1 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
C4 C1 C2 106.17(13)
C4 C1 H1A 110.5
C2 C1 H1A 110.5
C4 C1 H1B 110.5
C2 C1 H1B 110.5
H1A C1 H1B 108.7
C3 C2 C1 105.84(13)
C3 C2 H2A 110.6
C1 C2 H2A 110.6
C3 C2 H2B 110.6
C1 C2 H2B 110.6
H2A C2 H2B 108.7
O1 C3 N1 124.12(15)
O1 C3 C2 130.27(15)
N1 C3 C2 105.60(13)
O2 C4 N1 124.70(14)
O2 C4 C1 130.03(15)
N1 C4 C1 105.28(13)
O4 C5 O3 121.65(14)
O4 C5 C6 126.43(14)
O3 C5 C6 111.92(12)
C8 C6 C5 121.40(15)
C8 C6 C7 124.80(15)
C5 C6 C7 113.80(14)
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C6 C8 H8A 120.0
C6 C8 H8B 120.0
H8A C8 H8B 120.0
C3 N1 C4 117.01(13)
C3 N1 O3 120.89(13)
C4 N1 O3 122.09(13)
N1 O3 C5 111.51(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C4 1.502(2)
C1 C2 1.527(2)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.502(2)
C2 H2A 0.9900
C2 H2B 0.9900
C3 O1 1.202(2)
C3 N1 1.380(2)
C4 O2 1.2005(19)
C4 N1 1.383(2)
C5 O4 1.1894(18)
C5 O3 1.3895(18)
C5 C6 1.479(2)
C6 C8 1.322(2)
C6 C7 1.497(2)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9500
C8 H8B 0.9500
N1 O3 1.3862(15)
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
C7 H7A O2 3_665 0.98 2.54 3.393(2) 145
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
_geom_torsion_publ_flag
C4 C1 C2 C3 3.14(16) ?
C1 C2 C3 O1 179.04(17) ?
C1 C2 C3 N1 -1.86(16) ?
C2 C1 C4 O2 176.76(16) ?
C2 C1 C4 N1 -3.24(16) ?
O4 C5 C6 C8 179.43(16) ?
O3 C5 C6 C8 -0.8(2) yes
O4 C5 C6 C7 0.1(2) ?
O3 C5 C6 C7 179.94(13) yes
O1 C3 N1 C4 178.91(15) ?
C2 C3 N1 C4 -0.25(18) ?
O1 C3 N1 O3 -0.2(2) ?
C2 C3 N1 O3 -179.34(12) yes
O2 C4 N1 C3 -177.73(15) ?
C1 C4 N1 C3 2.28(18) ?
O2 C4 N1 O3 1.3(2) ?
C1 C4 N1 O3 -178.65(12) yes
C3 N1 O3 C5 84.50(16) yes
C4 N1 O3 C5 -94.54(16) ?
O4 C5 O3 N1 4.8(2) ?
C6 C5 O3 N1 -175.03(11) ?
