#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/25/2232522.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_2232522
loop_
_publ_author_name
'Zhu, Haifeng'
'Guo, Miao'
'Chen, Han'
'Jin, Haixiao'
'Liang, Hongze'
_publ_section_title
;
 2,5-Dioxopyrrolidin-1-yl 3-(furan-2-yl)acrylate
;
_journal_coeditor_code           YK2020
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2863
_journal_paper_doi               10.1107/S1600536811040566
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H9 N O5'
_chemical_formula_moiety         'C11 H9 N O5'
_chemical_formula_sum            'C11 H9 N O5'
_chemical_formula_weight         235.19
_chemical_name_systematic
;
2,5-Dioxopyrrolidin-1-yl 3-(furan-2-yl)acrylate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   10.3054(13)
_cell_length_b                   9.2376(12)
_cell_length_c                   21.892(3)
_cell_measurement_reflns_used    3779
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.71
_cell_volume                     2084.1(5)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker APEXII 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  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16939
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.86
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.236
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0348
_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)+(0.0285P)²+0.9232P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                1900
_reflns_number_total             2399
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            yk2020.cif
_cod_data_source_block           I
_cod_original_cell_volume        2084.0(5)
_cod_original_sg_symbol_Hall     '-p 2ac 2ab'
_cod_database_code               2232522
_cod_database_fobs_code          2232522
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'
'-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_symmetry_multiplicity
O O1 0.80658(9) 0.22692(10) 0.28201(4) 0.0261(2) Uani d . 1 1
O O2 0.89760(9) 0.55049(10) 0.10826(4) 0.0273(2) Uani d . 1 1
O O3 0.67881(9) 0.58836(11) 0.11454(5) 0.0314(2) Uani d . 1 1
O O4 0.81461(10) 0.44760(11) -0.00431(5) 0.0356(3) Uani d . 1 1
O O5 1.01727(10) 0.81990(11) 0.09170(5) 0.0349(3) Uani d . 1 1
C C6 0.68207(13) 0.36659(14) 0.21024(6) 0.0237(3) Uani d . 1 1
H H6A 0.6008 0.3944 0.1960 0.028 Uiso calc R 1 1
C C7 0.78634(13) 0.42777(14) 0.18443(6) 0.0244(3) Uani d . 1 1
H H7A 0.8686 0.4048 0.1989 0.029 Uiso calc R 1 1
N N8 0.89355(11) 0.63213(12) 0.05495(5) 0.0246(3) Uani d . 1 1
C C9 0.68679(12) 0.26114(14) 0.25831(6) 0.0220(3) Uani d . 1 1
C C10 0.77299(13) 0.52965(14) 0.13407(6) 0.0233(3) Uani d . 1 1
C C11 0.96337(13) 0.76125(14) 0.04991(6) 0.0243(3) Uani d . 1 1
C C12 0.59420(14) 0.18035(14) 0.28687(6) 0.0255(3) Uani d . 1 1
H H12A 0.5054 0.1829 0.2793 0.031 Uiso calc R 1 1
C C13 0.85503(13) 0.56972(15) 0.00020(6) 0.0250(3) Uani d . 1 1
C C14 0.65847(14) 0.09163(15) 0.33025(6) 0.0270(3) Uani d . 1 1
H H14A 0.6205 0.0249 0.3566 0.032 Uiso calc R 1 1
C C15 0.78534(14) 0.12362(15) 0.32556(6) 0.0279(3) Uani d . 1 1
H H15A 0.8503 0.0810 0.3489 0.034 Uiso calc R 1 1
C C16 0.87575(15) 0.68378(15) -0.04765(6) 0.0289(3) Uani d . 1 1
H H16A 0.7934 0.7229 -0.0614 0.035 Uiso calc R 1 1
H H16B 0.9214 0.6439 -0.0826 0.035 Uiso calc R 1 1
C C17 0.95729(14) 0.80146(15) -0.01663(6) 0.0286(3) Uani d . 1 1
H H17A 1.0438 0.8046 -0.0341 0.034 Uiso calc R 1 1
H H17B 0.9170 0.8956 -0.0217 0.034 Uiso calc R 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
C15 O1 C9 106.25(10)
N8 O2 C10 112.43(9)
C7 C6 C9 124.66(12)
C7 C6 H6A 117.7
C9 C6 H6A 117.7
C6 C7 C10 121.09(12)
C6 C7 H7A 119.5
C10 C7 H7A 119.5
C13 N8 O2 120.55(11)
C13 N8 C11 115.69(11)
O2 N8 C11 120.93(11)
C12 C9 O1 109.22(11)
C12 C9 C6 133.19(13)
O1 C9 C6 117.58(11)
O3 C10 O2 122.25(12)
O3 C10 C7 130.02(13)
O2 C10 C7 107.72(11)
O5 C11 N8 124.31(13)
O5 C11 C17 130.25(13)
N8 C11 C17 105.42(11)
C9 C12 C14 107.25(12)
C9 C12 H12A 126.4
C14 C12 H12A 126.4
O4 C13 N8 123.89(13)
O4 C13 C16 130.41(12)
N8 C13 C16 105.69(11)
C15 C14 C12 106.01(12)
C15 C14 H14A 127.0
C12 C14 H14A 127.0
C14 C15 O1 111.26(12)
C14 C15 H15A 124.4
O1 C15 H15A 124.4
C13 C16 C17 105.46(11)
C13 C16 H16A 110.6
C17 C16 H16A 110.6
C13 C16 H16B 110.6
C17 C16 H16B 110.6
H16A C16 H16B 108.8
C11 C17 C16 106.07(11)
C11 C17 H17A 110.5
C16 C17 H17A 110.5
C11 C17 H17B 110.5
C16 C17 H17B 110.5
H17A C17 H17B 108.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C15 1.3664(16)
O1 C9 1.3759(15)
O2 N8 1.3900(13)
O2 C10 1.4162(16)
O3 C10 1.1912(16)
O4 C13 1.2066(16)
O5 C11 1.1996(16)
C6 C7 1.3391(18)
C6 C9 1.4348(18)
C6 H6A 0.9300
C7 C10 1.4561(18)
C7 H7A 0.9300
N8 C13 1.3880(17)
N8 C11 1.3974(17)
C9 C12 1.3632(18)
C11 C17 1.5044(19)
C12 C14 1.4185(19)
C12 H12A 0.9300
C13 C16 1.5011(19)
C14 C15 1.344(2)
C14 H14A 0.9300
C15 H15A 0.9300
C16 C17 1.533(2)
C16 H16A 0.9700
C16 H16B 0.9700
C17 H17A 0.9700
C17 H17B 0.9700
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
C12 H12A O1 6_556 0.93 2.4831 3.3533(17) 155.80 yes
C14 H14A O5 6_546 0.9301 2.4502 3.3672(18) 168.93 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4872344
