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_4023800
_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 H9 Cl O2'
_chemical_formula_sum            'C12 H9 Cl O2'
_chemical_formula_weight         220.64
_chemical_name_systematic
; 
4-Chloro-biphenyl-2,5-diol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.0036(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4814(2)
_cell_length_b                   11.3273(3)
_cell_length_c                   11.7221(3)
_cell_measurement_reflns_used    2374
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     985.97(4)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       '\w scans at fixed \c = 55\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4332
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.51
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+0.3368P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                1800
_reflns_number_total             2257
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo801397g_si_002.cif
_cod_data_source_block           k07224
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023800