data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Andrew Westwell'
'Cedric J. Lion'
'Charles S. Matthews'
'Carl H. Schwalbe'
'Malcolm F.G. Stevens'
'David A. Vasselin'

_publ_contact_author_name        'Andrew Westwell'
_publ_contact_author_address     
;
School of Pharmacy
University of Nottingham
Centre for Biomolecular Sciences
University Park
Nottingham
NG7 2RD
UNITED KINGDOM
;

_publ_contact_author_email       ANDREW.WESTWELL@NOTTINGHAM.AC.UK

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
Novel reaction products from the hypervalent iodine
oxidation of hydroxylated -stilbenes and -isoflavones
;

data_dv246na
_database_code_depnum_ccdc_archive 'CCDC 279000'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            2,4'-dihydroxybenzil
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 O4'
_chemical_formula_weight         242.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y, -z-1/2'
'-x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z-1/2'

_cell_length_a                   17.771(5)
_cell_length_b                   10.833(2)
_cell_length_c                   15.115(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 124.564(18)
_cell_angle_gamma                90.00
_cell_volume                     2396.3(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9.37
_cell_measurement_theta_max      14.04

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       '\w/2\q scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        1
_diffrn_reflns_number            4305
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2112
_reflns_number_gt                1456
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Enraf-Nonius CAD4, 1989'
_computing_cell_refinement       'Enraf-Nonius CAD4, 1989'
_computing_data_reduction        'CADABS (Gould & Smith, 1986)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.7292P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0040(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2112
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1268
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.63671(15) 0.22124(15) 0.23989(15) 0.0824(6) Uani 1 1 d . . .
H01 H 0.645(2) 0.280(3) 0.204(2) 0.105(10) Uiso 1 1 d . . .
O2 O 0.66557(11) 0.44010(13) 0.19142(12) 0.0669(5) Uani 1 1 d . . .
O3 O 0.75932(9) 0.65159(13) 0.36549(13) 0.0735(5) Uani 1 1 d . . .
O4 O 0.41413(11) 0.96087(12) 0.02226(13) 0.0718(5) Uani 1 1 d . . .
H04 H 0.359(2) 0.918(3) -0.035(2) 0.110(10) Uiso 1 1 d . . .
C1 C 0.63705(14) 0.27900(18) 0.31852(17) 0.0532(5) Uani 1 1 d . . .
C2 C 0.62078(16) 0.2096(2) 0.3824(2) 0.0684(6) Uani 1 1 d . . .
H2 H 0.6090 0.1256 0.3694 0.082 Uiso 1 1 calc R . .
C3 C 0.62183(18) 0.2630(2) 0.4636(2) 0.0715(7) Uani 1 1 d . . .
H3 H 0.6107 0.2152 0.5062 0.086 Uiso 1 1 calc R . .
C4 C 0.63915(18) 0.3879(2) 0.4847(2) 0.0720(7) Uani 1 1 d . . .
H4 H 0.6401 0.4235 0.5413 0.086 Uiso 1 1 calc R . .
C5 C 0.65476(15) 0.45806(18) 0.42227(17) 0.0571(5) Uani 1 1 d . . .
H5 H 0.6665 0.5419 0.4367 0.069 Uiso 1 1 calc R . .
C6 C 0.65347(12) 0.40663(16) 0.33725(15) 0.0454(5) Uani 1 1 d . . .
C7 C 0.66614(12) 0.48094(17) 0.26760(15) 0.0461(5) Uani 1 1 d . . .
C8 C 0.68328(13) 0.61944(18) 0.28892(15) 0.0497(5) Uani 1 1 d . . .
C9 C 0.61173(12) 0.70599(15) 0.21810(14) 0.0432(4) Uani 1 1 d . . .
C10 C 0.52693(12) 0.66644(16) 0.13184(15) 0.0482(5) Uani 1 1 d . . .
H10 H 0.5154 0.5823 0.1189 0.058 Uiso 1 1 calc R . .
C11 C 0.46011(12) 0.74933(17) 0.06550(15) 0.0515(5) Uani 1 1 d . . .
H11 H 0.4036 0.7215 0.0079 0.062 Uiso 1 1 calc R . .
C12 C 0.47675(13) 0.87490(17) 0.08426(15) 0.0498(5) Uani 1 1 d . . .
C13 C 0.56118(14) 0.91566(18) 0.17092(16) 0.0574(6) Uani 1 1 d . . .
H13 H 0.5724 0.9998 0.1841 0.069 Uiso 1 1 calc R . .
C14 C 0.62741(13) 0.83294(17) 0.23643(16) 0.0527(5) Uani 1 1 d . . .
H14 H 0.6838 0.8610 0.2941 0.063 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.1308(16) 0.0478(9) 0.0891(12) -0.0146(9) 0.0748(12) -0.0141(9)
O2 0.0871(12) 0.0554(9) 0.0697(10) 0.0091(7) 0.0514(9) 0.0075(8)
O3 0.0464(9) 0.0582(9) 0.0715(10) 0.0133(7) 0.0069(8) -0.0083(7)
O4 0.0586(9) 0.0404(8) 0.0748(10) -0.0034(7) 0.0129(8) 0.0115(7)
C1 0.0591(12) 0.0417(10) 0.0611(12) -0.0016(9) 0.0354(10) -0.0009(9)
C2 0.0837(16) 0.0432(11) 0.0859(16) 0.0048(11) 0.0526(14) -0.0062(11)
C3 0.0901(17) 0.0608(14) 0.0845(17) 0.0136(12) 0.0620(14) 0.0011(12)
C4 0.0963(19) 0.0664(14) 0.0745(15) 0.0030(12) 0.0611(15) 0.0076(13)
C5 0.0690(13) 0.0427(10) 0.0649(13) 0.0011(9) 0.0411(11) 0.0043(9)
C6 0.0414(9) 0.0378(9) 0.0523(11) 0.0046(8) 0.0238(8) 0.0026(7)
C7 0.0405(9) 0.0435(10) 0.0489(11) 0.0051(8) 0.0222(8) 0.0050(8)
C8 0.0412(10) 0.0470(10) 0.0519(11) 0.0064(9) 0.0211(9) -0.0032(8)
C9 0.0394(9) 0.0375(9) 0.0471(10) 0.0012(8) 0.0211(8) -0.0041(8)
C10 0.0424(10) 0.0335(9) 0.0557(11) -0.0040(8) 0.0202(9) -0.0047(7)
C11 0.0384(9) 0.0406(10) 0.0550(11) -0.0072(8) 0.0142(8) -0.0041(8)
C12 0.0458(10) 0.0380(9) 0.0533(11) -0.0034(8) 0.0207(9) 0.0035(8)
C13 0.0573(12) 0.0337(9) 0.0613(12) -0.0080(9) 0.0218(10) -0.0067(9)
C14 0.0447(10) 0.0423(10) 0.0516(11) -0.0046(8) 0.0157(9) -0.0101(8)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C1 1.340(3) . ?
O1 H01 0.90(3) . ?
O2 C7 1.228(2) . ?
O3 C8 1.230(2) . ?
O4 C12 1.342(2) . ?
O4 H04 0.97(3) . ?
C1 C2 1.377(3) . ?
C1 C6 1.408(3) . ?
C2 C3 1.348(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.358(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.441(3) . ?
C7 C8 1.529(3) . ?
C8 C9 1.448(3) . ?
C9 C10 1.387(2) . ?
C9 C14 1.399(3) . ?
C10 C11 1.368(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(3) . ?
C13 C14 1.359(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

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
C1 O1 H01 106.4(19) . . ?
C12 O4 H04 107.8(18) . . ?
O1 C1 C2 118.01(19) . . ?
O1 C1 C6 122.21(19) . . ?
C2 C1 C6 119.8(2) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.22(18) . . ?
C5 C6 C7 121.63(17) . . ?
C1 C6 C7 120.13(18) . . ?
O2 C7 C6 124.21(17) . . ?
O2 C7 C8 116.47(17) . . ?
C6 C7 C8 119.31(18) . . ?
O3 C8 C9 123.19(17) . . ?
O3 C8 C7 117.23(16) . . ?
C9 C8 C7 119.56(15) . . ?
C10 C9 C14 118.54(16) . . ?
C10 C9 C8 121.64(16) . . ?
C14 C9 C8 119.82(16) . . ?
C11 C10 C9 120.97(16) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 119.88(16) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
O4 C12 C11 122.81(17) . . ?
O4 C12 C13 117.50(17) . . ?
C11 C12 C13 119.69(17) . . ?
C14 C13 C12 120.18(17) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 120.73(17) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?

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
O1 C1 C2 C3 178.9(2) . . . . ?
C6 C1 C2 C3 -1.0(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C4 C5 C6 C7 177.4(2) . . . . ?
O1 C1 C6 C5 -178.4(2) . . . . ?
C2 C1 C6 C5 1.5(3) . . . . ?
O1 C1 C6 C7 3.1(3) . . . . ?
C2 C1 C6 C7 -176.98(18) . . . . ?
C5 C6 C7 O2 -179.97(19) . . . . ?
C1 C6 C7 O2 -1.6(3) . . . . ?
C5 C6 C7 C8 1.2(3) . . . . ?
C1 C6 C7 C8 179.61(16) . . . . ?
O2 C7 C8 O3 -104.6(2) . . . . ?
C6 C7 C8 O3 74.3(3) . . . . ?
O2 C7 C8 C9 73.9(2) . . . . ?
C6 C7 C8 C9 -107.2(2) . . . . ?
O3 C8 C9 C10 179.4(2) . . . . ?
C7 C8 C9 C10 1.1(3) . . . . ?
O3 C8 C9 C14 -0.9(3) . . . . ?
C7 C8 C9 C14 -179.2(2) . . . . ?
C14 C9 C10 C11 0.4(3) . . . . ?
C8 C9 C10 C11 -179.84(19) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 O4 -180.0(2) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
O4 C12 C13 C14 -179.8(2) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C9 -0.2(3) . . . . ?
C10 C9 C14 C13 -0.3(3) . . . . ?
C8 C9 C14 C13 180.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.044