#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/57/2235704.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_2235704
loop_
_publ_author_name
'Han, Xin-Yi'
'Shi, Ya-Bin'
'Shen, Hong'
'Bai, Shu-Yuan'
'Wang, Hai-Bo'
_publ_section_title
;
 5-Nitro-1-benzofuran-2(3H)-one
;
_journal_coeditor_code           YK2051
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2029
_journal_paper_doi               10.1107/S1600536812025093
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C8 H5 N O4'
_chemical_formula_moiety         'C8 H5 N O4'
_chemical_formula_sum            'C8 H5 N O4'
_chemical_formula_weight         179.13
_chemical_melting_point          453
_chemical_name_systematic
;
5-Nitro-1-benzofuran-2(3H)-one
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.45(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4510(15)
_cell_length_b                   8.9150(18)
_cell_length_c                   11.249(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10
_cell_volume                     745.9(3)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1993)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1993)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2234
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         2.74
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  7200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_correction_T_min  0.9617
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.202
_refine_ls_extinction_coef       0.032(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0459
_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)+(0.1000P)²+0.0450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1463
_reflns_number_gt                1063
_reflns_number_total             1362
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            yk2051.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235704
_cod_database_fobs_code          2235704
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
N N 0.8821(2) 0.70812(19) 1.15062(16) 0.0546(5) Uani d . 1 1
O O2 0.6163(2) 0.01034(17) 0.87673(13) 0.0722(5) Uani d . 1 1
C C2 0.6559(3) 0.1292(2) 0.91761(18) 0.0539(5) Uani d . 1 1
O O1 0.62020(18) 0.25817(15) 0.85172(12) 0.0545(4) Uani d . 1 1
C C8 0.6802(2) 0.3797(2) 0.91898(15) 0.0433(5) Uani d . 1 1
O O3 0.9499(2) 0.67114(19) 1.24720(15) 0.0811(6) Uani d . 1 1
C C9 0.7562(2) 0.33732(19) 1.02933(14) 0.0404(5) Uani d . 1 1
O O4 0.8753(3) 0.83771(18) 1.11869(17) 0.1003(7) Uani d . 1 1
C C3 0.7447(3) 0.1713(2) 1.03692(16) 0.0535(5) Uani d . 1 1
H H3A 0.6724 0.1404 1.1015 0.064 Uiso calc R 1 1
H H3B 0.8632 0.1266 1.0482 0.064 Uiso calc R 1 1
C C7 0.6656(3) 0.5261(2) 0.88133(16) 0.0510(5) Uani d . 1 1
H H7A 0.6133 0.5509 0.8068 0.061 Uiso calc R 1 1
C C6 0.7322(2) 0.6344(2) 0.95957(16) 0.0499(5) Uani d . 1 1
H H6A 0.7259 0.7352 0.9385 0.060 Uiso calc R 1 1
C C5 0.8087(2) 0.59213(19) 1.06991(15) 0.0426(5) Uani d . 1 1
C C4 0.8230(2) 0.4451(2) 1.10729(15) 0.0417(5) Uani d . 1 1
H H4A 0.8755 0.4201 1.1818 0.050 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N 0.0607(10) 0.0423(10) 0.0606(11) -0.0029(7) 0.0005(8) -0.0091(8)
O2 0.0933(12) 0.0518(10) 0.0695(9) -0.0181(8) -0.0122(8) -0.0149(8)
C2 0.0595(11) 0.0472(11) 0.0541(11) -0.0113(9) -0.0035(9) -0.0039(9)
O1 0.0621(8) 0.0549(9) 0.0445(8) -0.0074(6) -0.0134(6) -0.0041(6)
C8 0.0433(9) 0.0457(11) 0.0401(9) -0.0042(8) -0.0045(7) -0.0030(7)
O3 0.1034(13) 0.0622(10) 0.0728(10) -0.0035(9) -0.0338(9) -0.0167(8)
C9 0.0400(9) 0.0397(9) 0.0405(9) -0.0032(7) -0.0051(7) 0.0012(7)
O4 0.170(2) 0.0362(9) 0.0916(13) -0.0105(10) -0.0194(12) -0.0042(9)
C3 0.0669(12) 0.0421(10) 0.0495(10) -0.0091(9) -0.0121(9) 0.0013(8)
C7 0.0555(11) 0.0544(12) 0.0418(9) 0.0021(9) -0.0089(8) 0.0076(8)
C6 0.0540(11) 0.0416(10) 0.0540(11) 0.0044(8) 0.0021(8) 0.0069(8)
C5 0.0394(9) 0.0399(10) 0.0483(10) 0.0002(7) -0.0004(7) -0.0032(8)
C4 0.0419(9) 0.0421(10) 0.0402(9) -0.0017(7) -0.0060(7) 0.0005(7)
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
O4 N O3 122.14(18)
O4 N C5 118.95(17)
O3 N C5 118.91(17)
O2 C2 O1 119.93(17)
O2 C2 C3 130.8(2)
O1 C2 C3 109.23(15)
C8 O1 C2 108.23(13)
C7 C8 O1 124.00(15)
C7 C8 C9 123.75(17)
O1 C8 C9 112.24(15)
C4 C9 C8 119.60(16)
C4 C9 C3 132.86(15)
C8 C9 C3 107.55(15)
C9 C3 C2 102.75(15)
C9 C3 H3A 111.2
C2 C3 H3A 111.2
C9 C3 H3B 111.2
C2 C3 H3B 111.2
H3A C3 H3B 109.1
C8 C7 C6 116.70(17)
C8 C7 H7A 121.6
C6 C7 H7A 121.6
C7 C6 C5 119.61(17)
C7 C6 H6A 120.2
C5 C6 H6A 120.2
C4 C5 C6 123.47(16)
C4 C5 N 117.66(16)
C6 C5 N 118.85(16)
C9 C4 C5 116.86(16)
C9 C4 H4A 121.6
C5 C4 H4A 121.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N O4 1.210(2)
N O3 1.216(2)
N C5 1.460(2)
O2 C2 1.185(2)
C2 O1 1.385(2)
C2 C3 1.508(3)
O1 C8 1.380(2)
C8 C7 1.374(2)
C8 C9 1.385(2)
C9 C4 1.374(2)
C9 C3 1.485(2)
C3 H3A 0.9700
C3 H3B 0.9700
C7 C6 1.379(3)
C7 H7A 0.9300
C6 C5 1.387(2)
C6 H6A 0.9300
C5 C4 1.378(3)
C4 H4A 0.9300
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 H3A O2 3_657 0.9700 2.5600 3.334(3) 137.00 yes
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
O2 C2 O1 C8 -179.61(18)
C3 C2 O1 C8 0.4(2)
C2 O1 C8 C7 -179.64(16)
C2 O1 C8 C9 0.0(2)
C7 C8 C9 C4 -0.5(3)
O1 C8 C9 C4 179.89(14)
C7 C8 C9 C3 179.23(17)
O1 C8 C9 C3 -0.40(19)
C4 C9 C3 C2 -179.74(18)
C8 C9 C3 C2 0.61(18)
O2 C2 C3 C9 179.4(2)
O1 C2 C3 C9 -0.6(2)
O1 C8 C7 C6 179.91(16)
C9 C8 C7 C6 0.3(3)
C8 C7 C6 C5 -0.1(3)
C7 C6 C5 C4 0.1(3)
C7 C6 C5 N 178.69(16)
O4 N C5 C4 178.15(17)
O3 N C5 C4 -1.0(2)
O4 N C5 C6 -0.5(3)
O3 N C5 C6 -179.70(17)
C8 C9 C4 C5 0.4(2)
C3 C9 C4 C5 -179.21(17)
C6 C5 C4 C9 -0.2(3)
N C5 C4 C9 -178.85(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 523032
