#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/32/2233233.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_2233233
loop_
_publ_author_name
'Wang, Hui'
'Liu, Changlu'
'Luo, Feihua'
_publ_section_title
;
 2-[(3S)-5-Oxooxolan-3-yl]isoindoline-1,3-dione
;
_journal_coeditor_code           LH5369
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o24
_journal_paper_doi               10.1107/S160053681105135X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C12 H9 N O4'
_chemical_formula_moiety         'C12 H9 N O4'
_chemical_formula_sum            'C12 H9 N O4'
_chemical_formula_weight         231.20
_chemical_name_systematic
;
2-[(3S)-5-Oxooxolan-3-yl]isoindoline-1,3-dione
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   5.7224(3)
_cell_length_b                   10.5839(5)
_cell_length_c                   16.8532(10)
_cell_measurement_reflns_used    2599
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.19
_cell_measurement_theta_min      2.27
_cell_volume                     1020.72(9)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4468
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_correction_T_min  0.9774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.100
_refine_diff_density_min         -0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.203
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.203
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0284
_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)+(0.0366P)²+0.0827P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0728
_reflns_number_gt                1002
_reflns_number_total             1077
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5369.cif
_cod_data_source_block           I
_cod_database_code               2233233
_cod_database_fobs_code          2233233
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_symmetry_multiplicity
C C1 0.8388(3) 0.49330(17) 0.93941(11) 0.0362(4) Uani d . 1 1
C C2 0.6577(4) 0.5765(2) 0.95245(13) 0.0445(5) Uani d . 1 1
H H2 0.5424 0.5900 0.9145 0.053 Uiso calc R 1 1
C C3 0.6548(4) 0.6395(2) 1.02494(13) 0.0493(5) Uani d . 1 1
H H3 0.5347 0.6960 1.0360 0.059 Uiso calc R 1 1
C C4 0.8280(4) 0.6193(2) 1.08081(13) 0.0501(5) Uani d . 1 1
H H4 0.8220 0.6627 1.1288 0.060 Uiso calc R 1 1
C C5 1.0100(4) 0.5361(2) 1.06693(13) 0.0470(5) Uani d . 1 1
H H5 1.1268 0.5232 1.1044 0.056 Uiso calc R 1 1
C C6 1.0115(3) 0.47294(17) 0.99517(11) 0.0365(4) Uani d . 1 1
C C7 1.1748(3) 0.37695(18) 0.96411(11) 0.0366(4) Uani d . 1 1
C C8 0.8880(3) 0.41079(18) 0.87031(11) 0.0371(4) Uani d . 1 1
C C9 1.2036(4) 0.2499(2) 0.83890(11) 0.0422(5) Uani d . 1 1
H H9 1.3392 0.2152 0.8669 0.051 Uiso calc R 1 1
C C10 1.0378(4) 0.1429(2) 0.81692(13) 0.0500(6) Uani d . 1 1
H H10A 1.1173 0.0621 0.8192 0.060 Uiso calc R 1 1
H H10B 0.9051 0.1408 0.8527 0.060 Uiso calc R 1 1
C C11 0.9611(4) 0.1714(2) 0.73468(13) 0.0449(5) Uani d . 1 1
C C12 1.2804(4) 0.2984(2) 0.75729(11) 0.0524(6) Uani d . 1 1
H H12A 1.2911 0.3898 0.7575 0.063 Uiso calc R 1 1
H H12B 1.4318 0.2639 0.7432 0.063 Uiso calc R 1 1
N N1 1.0948(3) 0.34698(16) 0.88763(9) 0.0351(4) Uani d . 1 1
O O1 1.3448(3) 0.33039(14) 0.99497(8) 0.0510(4) Uani d . 1 1
O O2 0.7776(3) 0.39782(15) 0.80953(9) 0.0510(4) Uani d . 1 1
O O3 1.1040(3) 0.25678(15) 0.70162(8) 0.0522(4) Uani d . 1 1
O O4 0.8005(3) 0.12687(16) 0.69809(11) 0.0653(5) 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
C2 C1 C6 121.98(18)
C2 C1 C8 130.15(18)
C6 C1 C8 107.87(16)
C1 C2 C3 117.1(2)
C1 C2 H2 121.5
C3 C2 H2 121.5
C4 C3 C2 121.0(2)
C4 C3 H3 119.5
C2 C3 H3 119.5
C3 C4 C5 121.5(2)
C3 C4 H4 119.3
C5 C4 H4 119.3
C6 C5 C4 117.4(2)
C6 C5 H5 121.3
C4 C5 H5 121.3
C1 C6 C5 121.05(19)
C1 C6 C7 108.61(16)
C5 C6 C7 130.32(19)
O1 C7 N1 124.45(19)
O1 C7 C6 129.62(19)
N1 C7 C6 105.93(15)
O2 C8 N1 124.41(18)
O2 C8 C1 129.20(18)
N1 C8 C1 106.39(16)
N1 C9 C10 113.28(16)
N1 C9 C12 113.13(18)
C10 C9 C12 102.07(17)
N1 C9 H9 109.4
C10 C9 H9 109.4
C12 C9 H9 109.4
C11 C10 C9 105.11(18)
C11 C10 H10A 110.7
C9 C10 H10A 110.7
C11 C10 H10B 110.7
C9 C10 H10B 110.7
H10A C10 H10B 108.8
O4 C11 O3 121.1(2)
O4 C11 C10 128.7(2)
O3 C11 C10 110.14(18)
O3 C12 C9 106.29(18)
O3 C12 H12A 110.5
C9 C12 H12A 110.5
O3 C12 H12B 110.5
C9 C12 H12B 110.5
H12A C12 H12B 108.7
C8 N1 C7 111.08(16)
C8 N1 C9 125.97(16)
C7 N1 C9 122.54(16)
C11 O3 C12 111.18(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.378(3)
C1 C6 1.381(3)
C1 C8 1.482(3)
C2 C3 1.392(3)
C2 H2 0.9300
C3 C4 1.383(3)
C3 H3 0.9300
C4 C5 1.384(3)
C4 H4 0.9300
C5 C6 1.382(3)
C5 H5 0.9300
C6 C7 1.476(3)
C7 O1 1.208(2)
C7 N1 1.404(2)
C8 O2 1.211(2)
C8 N1 1.394(2)
C9 N1 1.455(2)
C9 C10 1.523(3)
C9 C12 1.532(3)
C9 H9 0.9800
C10 C11 1.484(3)
C10 H10A 0.9700
C10 H10B 0.9700
C11 O4 1.203(2)
C11 O3 1.340(3)
C12 O3 1.446(3)
C12 H12A 0.9700
C12 H12B 0.9700
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
C6 C1 C2 C3 -0.3(3)
C8 C1 C2 C3 178.4(2)
C1 C2 C3 C4 0.4(3)
C2 C3 C4 C5 0.0(3)
C3 C4 C5 C6 -0.4(3)
C2 C1 C6 C5 -0.2(3)
C8 C1 C6 C5 -179.17(18)
C2 C1 C6 C7 178.63(17)
C8 C1 C6 C7 -0.3(2)
C4 C5 C6 C1 0.6(3)
C4 C5 C6 C7 -177.97(19)
C1 C6 C7 O1 -177.9(2)
C5 C6 C7 O1 0.8(4)
C1 C6 C7 N1 2.3(2)
C5 C6 C7 N1 -179.1(2)
C2 C1 C8 O2 -0.4(4)
C6 C1 C8 O2 178.5(2)
C2 C1 C8 N1 179.41(19)
C6 C1 C8 N1 -1.7(2)
N1 C9 C10 C11 100.02(19)
C12 C9 C10 C11 -21.9(2)
C9 C10 C11 O4 -165.3(2)
C9 C10 C11 O3 16.2(2)
N1 C9 C12 O3 -101.25(19)
C10 C9 C12 O3 20.8(2)
O2 C8 N1 C7 -176.92(19)
C1 C8 N1 C7 3.3(2)
O2 C8 N1 C9 -4.1(3)
C1 C8 N1 C9 176.10(18)
O1 C7 N1 C8 176.68(18)
C6 C7 N1 C8 -3.45(19)
O1 C7 N1 C9 3.6(3)
C6 C7 N1 C9 -176.58(16)
C10 C9 N1 C8 -52.5(3)
C12 C9 N1 C8 63.0(2)
C10 C9 N1 C7 119.54(18)
C12 C9 N1 C7 -124.9(2)
O4 C11 O3 C12 178.82(19)
C10 C11 O3 C12 -2.6(2)
C9 C12 O3 C11 -12.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657345
