Chlorination Increases the Persistence of Semiquinone Free Radicals Derived from Polychlorinated Biphenyl Hydroquinones and Quinones
Yang Song; Garry R. Buettner; Sean Parkin; Brett A. Wagner; Larry W. Robertson; Hans-Joachim Lehmler; Journal of Organic Chemistry 73 (2008) 8296–8304; doi:10.1021/jo801397g

data_4023802
_publ_contact_author_address
;The University of Iowa
Department of Occupational and Environmental Health
100 Oakdale Campus, 124 IREH
Iowa City, IA 52242-5000
USA
;
_publ_contact_author_email       hans-joachim-lehmler@uiowa.edu
_publ_contact_author_fax         '1 (319) 335-4290'
_publ_contact_author_name        'Hans-Joachim Lehmler'
_publ_contact_author_phone       '1 (319) 335-4211'
_publ_section_title
;
 Chlorination Increases the Persistence of Semiquinone Free Radicals
 Derived from Polychlorinated Biphenyl Hydroquinones and Quinones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8296
_journal_page_last               8304
_journal_paper_doi               10.1021/jo801397g
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C12 H7 Cl3 O2'
_chemical_formula_sum            'C12 H7 Cl3 O2'
_chemical_formula_weight         289.53
_chemical_name_systematic
; 
3,6,4'-Trichloro-biphenyl-2,5-diol
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.896(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2876(4)
_cell_length_b                   9.0426(4)
_cell_length_c                   13.8328(7)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      69.19
_cell_measurement_theta_min      4.82
_cell_volume                     1147.76(9)
_computing_cell_refinement       'APEX2 (Bruker-AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker-AXS, 2006)'
_computing_data_reduction        'APEX2 (Bruker-AXS, 2006)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
; 
SHELX97-2 (Sheldrick, 2008) and local procedures 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker X8 Proteum diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'graded multilayer optics'
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15828
_diffrn_reflns_theta_full        69.28
_diffrn_reflns_theta_max         69.28
_diffrn_reflns_theta_min         4.82
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.113
_exptl_absorpt_correction_T_max  0.871
_exptl_absorpt_correction_T_min  0.553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs in APEX2 (BrukerAXS, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0252
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0403P)^2^+0.6092P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0703
_reflns_number_gt                2022
_reflns_number_total             2126
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo801397g_si_004.cif
_cod_data_source_block           x08071
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023802