#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/07/2100715.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_2100715
loop_
_publ_author_name
'Krešimir Molčanov'
'Mario Roboz'
'Biserka Kojić-Prodić'
_publ_section_title
;
 Structural characterization of p-benzosemiquinone radical in a
 solid state: the radical stabilization by a low-barrier hydrogen bond
;
_journal_coeditor_code           WS5041
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              1051
_journal_page_last               1060
_journal_paper_doi               10.1107/S0108768106038870
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C6 H5 O2'
_chemical_formula_sum            'C6 H5 O2'
_chemical_formula_weight         109.1
_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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 108.7900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.8362(2)
_cell_length_b                   5.9980(3)
_cell_length_c                   11.5007(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8
_cell_measurement_theta_min      8.1
_cell_volume                     250.52(2)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54179
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            601
_diffrn_reflns_theta_full        75.97
_diffrn_reflns_theta_max         75.97
_diffrn_reflns_theta_min         8.14
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.919
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             114
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.153
_refine_ls_extinction_coef       0.025(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   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     50
_refine_ls_number_reflns         523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0454P)²+0.0735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.106
_reflns_number_gt                412
_reflns_number_total             523
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ws5041.cif
_cod_data_source_block           sqm293k
_cod_database_code               2100715
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
H H3 -0.028(5) 0.486(3) 0.2924(18) 0.041(5) Uiso d . 1
H H2 0.305(6) 0.216(4) 0.639(2) 0.052(5) Uiso d . 1
H H1 0.421(16) 0.067(10) 0.474(6) 0.09(2) Uiso d P 0.5
O O1 0.3177(4) 0.1598(2) 0.41739(13) 0.0512(5) Uani d . 1
C C1 0.1673(4) 0.3216(3) 0.45904(15) 0.0337(4) Uani d . 1
C C3 -0.0196(4) 0.4930(3) 0.37616(15) 0.0354(4) Uani d . 1
C C2 0.1830(4) 0.3351(3) 0.58420(15) 0.0354(5) Uani d . 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
O1 0.0616(9) 0.0377(8) 0.0502(9) 0.0145(7) 0.0124(6) -0.0086(6)
C1 0.0360(8) 0.0289(8) 0.0373(8) 0.0034(7) 0.0135(6) -0.0033(7)
C3 0.0400(8) 0.0375(9) 0.0296(8) 0.0034(7) 0.0127(6) 0.0012(7)
C2 0.0373(8) 0.0306(8) 0.0371(9) 0.0049(7) 0.0105(6) 0.0057(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 2 1
0 2 -3
1 3 2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle
C1 O1 H1 . 111(4)
O1 C1 C2 . 122.51(16)
O1 C1 C3 . 118.65(15)
C2 C1 C3 . 118.83(14)
C2 C3 C1 3_566 120.58(14)
C2 C3 H3 3_566 120.1(12)
C1 C3 H3 . 119.3(12)
C3 C2 C1 3_566 120.58(15)
C3 C2 H2 3_566 121.1(13)
C1 C2 H2 . 118.2(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.297(2)
O1 H1 . 0.85(6)
C1 C2 . 1.424(2)
C1 C3 . 1.428(2)
C3 C2 3_566 1.359(2)
C3 H3 . 0.955(19)
C2 C3 3_566 1.359(2)
C2 H2 . 0.97(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 785
