#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/07/2100716.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_2100716 loop_ _publ_author_name 'Kre\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 109.99(8) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 3.770(3) _cell_length_b 5.980(3) _cell_length_c 11.458(14) _cell_measurement_reflns_used 16 _cell_measurement_temperature 90(2) _cell_measurement_theta_max 25.8 _cell_measurement_theta_min 8.2 _cell_volume 242.8(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-86 (Sheldrick, 1986)' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 1 _diffrn_measurement_device '\k-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 1.54184 _diffrn_reflns_av_R_equivalents 0.1017 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_number 531 _diffrn_reflns_theta_full 75.78 _diffrn_reflns_theta_max 75.78 _diffrn_reflns_theta_min 8.23 _diffrn_standards_decay_% 2 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.948 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 114 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.33 _refine_diff_density_min -0.416 _refine_ls_extinction_coef 0.053(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 50 _refine_ls_number_reflns 507 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.087 _refine_ls_R_factor_gt 0.0466 _refine_ls_shift/su_max 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0849P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.131 _reflns_number_gt 382 _reflns_number_total 507 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ws5041.cif _cod_data_source_block sqm90k _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2100716 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 O O1 0.5021(4) 0.3395(2) 0.41682(13) 0.0242(5) Uani d . 1 C C1 1.0156(5) -0.1659(3) 0.41428(16) 0.0169(5) Uani d . 1 C C2 0.7654(5) 0.0050(3) 0.37502(17) 0.0166(5) Uani d . 1 C C3 0.7420(5) 0.1783(3) 0.45841(17) 0.0162(5) Uani d . 1 H H2 0.610(6) 0.015(4) 0.294(2) 0.019(5) Uiso d . 1 H H1 1.025(7) -0.283(5) 0.357(3) 0.029(6) Uiso d . 1 H H3 0.498(14) 0.429(7) 0.478(4) 0.018(12) Uiso d P 0.5 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 0.0334(9) 0.0161(8) 0.0254(8) 0.0090(6) 0.0132(6) 0.0041(6) C1 0.0185(9) 0.0141(9) 0.0197(9) -0.0012(7) 0.0086(7) -0.0015(7) C2 0.0158(8) 0.0175(9) 0.0161(8) -0.0014(7) 0.0051(6) -0.0021(8) C3 0.0144(8) 0.0136(8) 0.0206(9) 0.0009(7) 0.0061(6) 0.0013(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 -1 -1 2 -2 -1 -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_site_symmetry_3 _geom_angle C3 O1 H3 . . 111(3) C2 C1 C3 . 3_756 120.29(17) C2 C1 H1 . . 120.1(16) C3 C1 H1 3_756 . 119.6(16) C1 C2 C3 . . 121.15(18) C1 C2 H2 . . 121.1(15) C3 C2 H2 . . 117.8(16) O1 C3 C2 . . 119.16(18) O1 C3 C1 . 3_756 122.30(18) C2 C3 C1 . 3_756 118.54(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance O1 C3 . 1.296(2) O1 H3 . 0.88(4) C1 C2 . 1.359(3) C1 C3 3_756 1.434(3) C1 H1 . 0.97(3) C2 C3 . 1.433(3) C2 H2 . 0.92(2) C3 C1 3_756 1.434(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 785