#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/74/2107461.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_2107461
loop_
_publ_author_name
'Wang, Ai'
'Ashurov, Jamshid'
'Ibragimov, Aziz'
'Wang, Ruimin'
'Mouhib, Halima'
'Mukhamedov, Nasir'
'Englert, Ulli'
_publ_section_title
;
 Charge density of the biologically active molecule
 (2-oxo-1,3-benzoxazol-3(2H)-yl)acetic acid
;
_journal_coeditor_code           PI5027
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              142
_journal_page_last               150
_journal_paper_doi               10.1107/S2052520615023690
_journal_volume                  72
_journal_year                    2016
_chemical_formula_moiety         'C9   H7   N   O4'
_chemical_formula_sum            'C9 H7 N O4'
_chemical_formula_weight         193.16
_chemical_name_common            (1)
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 104.6104(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.7600(2)
_cell_length_b                   8.05930(10)
_cell_length_c                   16.6668(2)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      50.73
_cell_measurement_theta_min      2.53
_cell_volume                     1658.53(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            58565
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         50.925
_diffrn_reflns_theta_min         2.526
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.9790
_exptl_absorpt_correction_T_min  0.9720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.800
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         9043
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0732P)²+0.2714P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1445
_reflns_number_gt                6814
_reflns_number_total             9043
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            pi5027sup1.cif
_cod_data_source_block           iam
_cod_depositor_comments
;Adding full bibliography for 2107461.cif.

 Adding full bibliography for 2107461.cif.
;
_cod_original_formula_sum        'C9   H7   N   O4'
_cod_database_code               2107461
_cod_database_fobs_code          2107461
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.979
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_occupancy
O O1 0.18601(3) 0.58635(5) 0.47510(2) 0.01809(6) Uani d 1
O O2 0.27404(3) 0.47052(6) 0.59703(3) 0.02161(7) Uani d 1
O O3 0.22896(4) 0.83705(6) 0.70231(3) 0.02142(7) Uani d 1
O O4 0.13927(4) 0.74431(7) 0.79363(3) 0.02593(9) Uani d 1
H H4O 0.1764(10) 0.8181(14) 0.8237(8) 0.031 Uiso d 1
N N1 0.11396(3) 0.61857(6) 0.58221(3) 0.01629(6) Uani d 1
C C1 0.09240(4) 0.68007(6) 0.44917(3) 0.01628(7) Uani d 1
C C2 0.04911(4) 0.74467(7) 0.37141(3) 0.01941(8) Uani d 1
H H2C 0.0824 0.7294 0.3270 0.023 Uiso calc 1
C C3 -0.04724(5) 0.83432(7) 0.36200(4) 0.02120(8) Uani d 1
H H3C -0.0807 0.8817 0.3096 0.025 Uiso calc 1
C C4 -0.09540(4) 0.85577(8) 0.42782(4) 0.02125(8) Uani d 1
H H4C -0.1610 0.9168 0.4190 0.026 Uiso calc 1
C C5 -0.04946(4) 0.78967(7) 0.50654(3) 0.01943(8) Uani d 1
H H5C -0.0820 0.8043 0.5514 0.023 Uiso calc 1
C C6 0.04597(4) 0.70179(6) 0.51543(3) 0.01583(6) Uani d 1
C C7 0.19795(4) 0.55086(6) 0.55707(3) 0.01668(7) Uani d 1
C C8 0.10322(4) 0.60853(7) 0.66614(3) 0.01780(7) Uani d 1
H H8A 0.1303 0.4994 0.6898 0.021 Uiso calc 1
H H8B 0.0256 0.6159 0.6655 0.021 Uiso calc 1
C C9 0.16468(4) 0.74452(6) 0.72125(3) 0.01656(7) Uani d 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
C7 O1 C1 107.19(4)
C9 O4 H4O 108.1(10)
C7 N1 C6 109.05(4)
C7 N1 C8 123.49(4)
C6 N1 C8 127.41(4)
C2 C1 O1 127.51(4)
C2 C1 C6 123.38(5)
O1 C1 C6 109.11(4)
C1 C2 C3 115.67(5)
C1 C2 H2C 122.2
C3 C2 H2C 122.2
C4 C3 C2 121.57(5)
C4 C3 H3C 119.2
C2 C3 H3C 119.2
C3 C4 C5 121.72(5)
C3 C4 H4C 119.1
C5 C4 H4C 119.1
C6 C5 C4 116.37(5)
C6 C5 H5C 121.8
C4 C5 H5C 121.8
C5 C6 C1 121.29(5)
C5 C6 N1 133.11(4)
C1 C6 N1 105.59(4)
O2 C7 N1 128.85(5)
O2 C7 O1 122.09(4)
N1 C7 O1 109.05(4)
N1 C8 C9 112.71(4)
N1 C8 H8A 109.0
C9 C8 H8A 109.0
N1 C8 H8B 109.0
C9 C8 H8B 109.0
H8A C8 H8B 107.8
O3 C9 O4 125.21(5)
O3 C9 C8 124.74(4)
O4 C9 C8 110.03(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.3662(6)
O1 C1 1.3869(6)
O2 C7 1.2163(6)
O3 C9 1.2080(6)
O4 C9 1.3259(6)
O4 H4O 0.842(8)
N1 C7 1.3595(6)
N1 C6 1.3979(7)
N1 C8 1.4419(6)
C1 C2 1.3765(7)
C1 C6 1.3898(6)
C2 C3 1.4003(8)
C2 H2C 0.9500
C3 C4 1.3968(9)
C3 H3C 0.9500
C4 C5 1.4002(8)
C4 H4C 0.9500
C5 C6 1.3839(7)
C5 H5C 0.9500
C8 C9 1.5154(7)
C8 H8A 0.9900
C8 H8B 0.9900
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 737119
