#------------------------------------------------------------------------------ #$Date: 2025-08-19 12:01:59 +0200 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/07/2100717.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_2100717 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 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 111.121(3) _cell_angle_beta 89.936(4) _cell_angle_gamma 92.453(4) _cell_formula_units_Z 1 _cell_length_a 3.8291(2) _cell_length_b 5.7546(3) _cell_length_c 5.9771(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.4 _cell_measurement_theta_min 11.6 _cell_volume 122.730(10) _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 0.994 _diffrn_measured_fraction_theta_max 0.994 _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 1.54179 _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 654 _diffrn_reflns_theta_full 76.2 _diffrn_reflns_theta_max 76.2 _diffrn_reflns_theta_min 7.95 _diffrn_standards_decay_% 10 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.938 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rod _exptl_crystal_F_000 51 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.238 _refine_diff_density_min -0.25 _refine_ls_extinction_coef 0.06(2) _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 1.036 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 50 _refine_ls_number_reflns 513 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_gt 0.0431 _refine_ls_shift/su_max 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0702P)^2^+0.0343P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1239 _reflns_number_gt 409 _reflns_number_total 513 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ws5041.cif _cod_data_source_block sqt293k _cod_database_code 2100717 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 H2 0.283(5) 0.081(4) 0.367(4) 0.039(5) Uiso d . 1 H H3 0.636(6) 0.221(4) 0.104(4) 0.047(6) Uiso d . 1 H H1 0.057(13) 0.458(10) 0.926(8) 0.051(13) Uiso d P 0.5 C C2 0.3722(4) 0.2500(3) 0.4123(3) 0.0326(5) Uani d . 1 O O1 0.0890(4) 0.3286(2) 0.7807(2) 0.0443(5) Uani d . 1 C C1 0.2853(4) 0.4142(3) 0.6475(3) 0.0303(5) Uani d . 1 C C3 0.5823(4) 0.3332(3) 0.2716(3) 0.0332(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 C2 0.0360(9) 0.0285(8) 0.0311(9) -0.0050(6) 0.0030(6) 0.0089(7) O1 0.0562(9) 0.0428(8) 0.0340(8) -0.0080(6) 0.0146(6) 0.0153(6) C1 0.0306(8) 0.0337(9) 0.0279(8) -0.0023(6) 0.0061(6) 0.0129(7) C3 0.0368(9) 0.0335(9) 0.0266(8) -0.0016(7) 0.0069(7) 0.0078(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 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 0 -1 -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 C2 C1 . . 120.25(15) C3 C2 H2 . . 123.6(13) C1 C2 H2 . . 116.0(13) C1 O1 H1 . . 108(3) O1 C1 C3 . 2_666 122.10(14) O1 C1 C2 . . 119.06(14) C3 C1 C2 2_666 . 118.84(14) C2 C3 C1 . 2_666 120.90(14) C2 C3 H3 . . 120.8(13) C1 C3 H3 2_666 . 118.2(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance C2 C3 . 1.356(2) C2 C1 . 1.431(2) C2 H2 . 0.96(2) O1 C1 . 1.3004(19) O1 H1 . 0.93(5) C1 C3 2_666 1.426(2) C3 C1 2_666 1.426(2) C3 H3 . 1.00(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 785