#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/07/2100714.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_2100714
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           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                110.800(15)
_cell_angle_beta                 91.164(12)
_cell_angle_gamma                91.443(15)
_cell_formula_units_Z            1
_cell_length_a                   3.7615(6)
_cell_length_b                   5.6996(12)
_cell_length_c                   5.9065(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      8.3
_cell_volume                     118.28(4)
_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  0.0557
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            1075
_diffrn_reflns_theta_full        76.39
_diffrn_reflns_theta_max         76.39
_diffrn_reflns_theta_min         8.03
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.973
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             51
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.2
_refine_ls_extinction_coef       0.054(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     50
_refine_ls_number_reflns         499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0482P)²+0.0384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1055
_reflns_number_gt                422
_reflns_number_total             499
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ws5041.cif
_cod_data_source_block           sqt90k
_cod_database_code               2100714
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
H H1 0.275(4) 0.076(3) 0.359(3) 0.016(4) Uiso d . 1
H H2 0.641(4) 0.216(3) 0.101(3) 0.018(4) Uiso d . 1
H H3 0.046(14) 0.459(11) 0.931(8) 0.050(14) Uiso d P 0.5
C C1 0.3718(3) 0.2476(2) 0.4109(2) 0.0136(4) Uani d . 1
O O1 0.0852(3) 0.32797(18) 0.78144(16) 0.0180(4) Uani d . 1
C C3 0.2827(3) 0.4133(2) 0.6480(2) 0.0126(4) Uani d . 1
C C2 0.5838(3) 0.3307(2) 0.2693(2) 0.0133(4) 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
C1 0.0130(7) 0.0126(6) 0.0150(7) -0.0012(5) -0.0016(5) 0.0050(5)
O1 0.0238(6) 0.0169(6) 0.0139(6) -0.0017(4) 0.0038(4) 0.0062(4)
C3 0.0113(7) 0.0153(7) 0.0126(7) -0.0010(5) 0.0003(5) 0.0065(5)
C2 0.0130(7) 0.0143(7) 0.0115(7) 0.0000(5) 0.0004(5) 0.0031(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009 '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 0.049 0.032 '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 2
1 2 1
-2 2 -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_site_symmetry_3
_geom_angle
C2 C1 C3 . . 120.45(11)
C2 C1 H1 . . 122.5(10)
C3 C1 H1 . . 117.0(10)
C3 O1 H3 . . 110(4)
O1 C3 C1 . . 119.24(11)
O1 C3 C2 . 2_666 121.98(11)
C1 C3 C2 . 2_666 118.78(12)
C1 C2 C3 . 2_666 120.76(12)
C1 C2 H2 . . 120.4(10)
C3 C2 H2 2_666 . 118.8(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.3599(18)
C1 C3 . 1.4357(19)
C1 H1 . 0.972(18)
O1 C3 . 1.2988(16)
O1 H3 . 0.95(5)
C3 C2 2_666 1.4378(17)
C2 C3 2_666 1.4378(17)
C2 H2 . 1.007(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 785
