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#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/38/4023802.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4023802
loop_
_publ_author_name
'Yang Song'
'Garry R. Buettner'
'Sean Parkin'
'Brett A. Wagner'
'Larry W. Robertson'
'Hans-Joachim Lehmler'
_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       'φ and ω 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/[σ²(Fo²)+(0.0403P)²+0.6092P] where P=(Fo²+2Fc²)/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     >2σ(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
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.05353(4) 0.33680(4) 0.83080(3) 0.02190(12) Uani 1 1 d . . .
Cl1' Cl 0.16598(4) 0.49153(4) 0.42807(3) 0.01904(12) Uani 1 1 d . . .
Cl2' Cl 0.72274(4) 0.10296(4) 0.49198(2) 0.01812(12) Uani 1 1 d . . .
O1' O 0.37356(11) 0.44950(12) 0.28849(7) 0.0178(2) Uani 1 1 d . . .
H1' H 0.2934 0.4931 0.2869 0.027 Uiso 1 1 calc R . .
O2' O 0.52503(11) 0.13805(13) 0.63303(7) 0.0182(2) Uani 1 1 d . . .
H2' H 0.4559 0.1321 0.6655 0.027 Uiso 1 1 calc R . .
C1 C 0.25659(16) 0.30675(16) 0.61166(10) 0.0145(3) Uani 1 1 d . . .
C2 C 0.29589(16) 0.38529(17) 0.69804(11) 0.0166(3) Uani 1 1 d . . .
H2 H 0.3878 0.4334 0.7100 0.020 Uiso 1 1 calc R . .
C3 C 0.20236(17) 0.39434(17) 0.76723(11) 0.0180(3) Uani 1 1 d . . .
H3 H 0.2286 0.4492 0.8259 0.022 Uiso 1 1 calc R . .
C4 C 0.07014(16) 0.32138(17) 0.74848(11) 0.0161(3) Uani 1 1 d . . .
C5 C 0.03049(17) 0.23816(17) 0.66496(11) 0.0175(3) Uani 1 1 d . . .
H5 H -0.0592 0.1858 0.6549 0.021 Uiso 1 1 calc R . .
C6 C 0.12399(16) 0.23240(17) 0.59606(11) 0.0158(3) Uani 1 1 d . . .
H6 H 0.0972 0.1771 0.5376 0.019 Uiso 1 1 calc R . .
C1' C 0.35462(16) 0.30292(17) 0.53592(10) 0.0143(3) Uani 1 1 d . . .
C2' C 0.32000(16) 0.38135(16) 0.44864(11) 0.0149(3) Uani 1 1 d . . .
C3' C 0.40729(16) 0.37510(17) 0.37566(10) 0.0150(3) Uani 1 1 d . . .
C4' C 0.53266(16) 0.29049(17) 0.39022(10) 0.0157(3) Uani 1 1 d . . .
H4' H 0.5938 0.2857 0.3413 0.019 Uiso 1 1 calc R . .
C5' C 0.56810(16) 0.21302(17) 0.47666(11) 0.0151(3) Uani 1 1 d . . .
C6' C 0.48181(16) 0.21800(17) 0.55039(10) 0.0149(3) Uani 1 1 d . . .
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 0.0000 0.0000 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3' O1' H1' 109.5 . . ?
C6' O2' H2' 109.5 . . ?
C2 C1 C6 119.29(14) . . ?
C2 C1 C1' 120.56(13) . . ?
C6 C1 C1' 120.14(13) . . ?
C1 C2 C3 120.86(14) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 118.29(14) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C5 C4 C3 122.10(14) . . ?
C5 C4 Cl1 118.22(12) . . ?
C3 C4 Cl1 119.67(12) . . ?
C4 C5 C6 118.79(14) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 120.61(14) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C2' C1' C6' 118.70(13) . . ?
C2' C1' C1 120.83(13) . . ?
C6' C1' C1 120.46(13) . . ?
C3' C2' C1' 121.73(13) . . ?
C3' C2' Cl1' 117.65(11) . . ?
C1' C2' Cl1' 120.62(11) . . ?
O1' C3' C4' 118.15(13) . . ?
O1' C3' C2' 122.55(13) . . ?
C4' C3' C2' 119.31(13) . . ?
C5' C4' C3' 119.33(13) . . ?
C5' C4' H4' 120.3 . . ?
C3' C4' H4' 120.3 . . ?
C4' C5' C6' 122.06(14) . . ?
C4' C5' Cl2' 118.64(11) . . ?
C6' C5' Cl2' 119.28(11) . . ?
O2' C6' C5' 118.05(13) . . ?
O2' C6' C1' 123.08(13) . . ?
C5' C6' C1' 118.87(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.7436(15) . ?
Cl1' C2' 1.7303(15) . ?
Cl2' C5' 1.7332(15) . ?
O1' C3' 1.3740(18) . ?
O1' H1' 0.8400 . ?
O2' C6' 1.3597(18) . ?
O2' H2' 0.8400 . ?
C1 C2 1.389(2) . ?
C1 C6 1.390(2) . ?
C1 C1' 1.491(2) . ?
C2 C3 1.391(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(2) . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C1' C2' 1.394(2) . ?
C1' C6' 1.397(2) . ?
C2' C3' 1.390(2) . ?
C3' C4' 1.382(2) . ?
C4' C5' 1.381(2) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.392(2) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -2.2(2) . . . . ?
C1' C1 C2 C3 177.35(13) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C2 C3 C4 C5 1.5(2) . . . . ?
C2 C3 C4 Cl1 -177.15(11) . . . . ?
C3 C4 C5 C6 -2.5(2) . . . . ?
Cl1 C4 C5 C6 176.09(11) . . . . ?
C4 C5 C6 C1 1.2(2) . . . . ?
C2 C1 C6 C5 1.0(2) . . . . ?
C1' C1 C6 C5 -178.46(13) . . . . ?
C2 C1 C1' C2' -107.22(17) . . . . ?
C6 C1 C1' C2' 72.28(19) . . . . ?
C2 C1 C1' C6' 74.07(19) . . . . ?
C6 C1 C1' C6' -106.44(17) . . . . ?
C6' C1' C2' C3' 1.0(2) . . . . ?
C1 C1' C2' C3' -177.71(13) . . . . ?
C6' C1' C2' Cl1' -178.54(11) . . . . ?
C1 C1' C2' Cl1' 2.7(2) . . . . ?
C1' C2' C3' O1' 178.81(13) . . . . ?
Cl1' C2' C3' O1' -1.6(2) . . . . ?
C1' C2' C3' C4' -0.8(2) . . . . ?
Cl1' C2' C3' C4' 178.79(11) . . . . ?
O1' C3' C4' C5' -179.15(13) . . . . ?
C2' C3' C4' C5' 0.5(2) . . . . ?
C3' C4' C5' C6' -0.4(2) . . . . ?
C3' C4' C5' Cl2' 178.01(11) . . . . ?
C4' C5' C6' O2' 179.93(14) . . . . ?
Cl2' C5' C6' O2' 1.51(19) . . . . ?
C4' C5' C6' C1' 0.7(2) . . . . ?
Cl2' C5' C6' C1' -177.76(11) . . . . ?
C2' C1' C6' O2' 179.83(13) . . . . ?
C1 C1' C6' O2' -1.4(2) . . . . ?
C2' C1' C6' C5' -0.9(2) . . . . ?
C1 C1' C6' C5' 177.80(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658783
