#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/40/2104098.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_2104098
loop_
_publ_author_name
'Cox, Philip J.'
'Kechagias, Dimitrios'
'Kelly, Orla'
_publ_section_title
;
 Conformations of substituted benzophenones
;
_journal_coeditor_code           WS5060
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              206
_journal_page_last               216
_journal_paper_doi               10.1107/S0108768108000232
_journal_volume                  64
_journal_year                    2008
_chemical_formula_moiety         'C13 H10 O3'
_chemical_formula_sum            'C13 H10 O3'
_chemical_formula_weight         214.21
_chemical_name_common
;
3,4-Dihydroxybenzophenone
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 115.019(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.4619(9)
_cell_length_b                   7.3737(2)
_cell_length_c                   12.3961(4)
_cell_measurement_reflns_used    11394
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     2026.14(12)
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_collection
;
        DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998)
;
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics
;
        PLATON (Spek,2002)
;
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,1999)'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
        Bruker-Nonius 95mm CCD camers on κ-goniostat
;
_diffrn_measurement_method
;
        φ and ω scans to fill Ewald sphere
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16476
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.91
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.1
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.9134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995, 1997)
;
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0555P)²+1.1706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1139
_reflns_number_gt                1733
_reflns_number_total             2319
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ws5060.cif
_cod_data_source_block           orla2
_cod_original_cell_volume        2026.14(11)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2104098
_cod_database_fobs_code          2104098
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'
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
O O1 0.66586(5) 0.08148(16) 0.40009(9) 0.0243(3) Uani d . 1
O O2 0.56113(5) 0.05271(16) 0.75039(10) 0.0242(3) Uani d . 1
H H2 0.5968(9) -0.006(3) 0.8012(16) 0.029 Uiso d . 1
O O3 0.46801(5) 0.24018(16) 0.58310(10) 0.0270(3) Uani d . 1
H H3 0.4682(8) 0.172(3) 0.6473(17) 0.032 Uiso d . 1
C C1 0.62252(7) 0.1488(2) 0.53207(13) 0.0185(3) Uani d . 1
C C2 0.61879(7) 0.0841(2) 0.63465(13) 0.0185(3) Uani d . 1
H H2A 0.6517 0.0193 0.6925 0.022 Uiso calc R 1
C C3 0.56755(7) 0.1140(2) 0.65227(13) 0.0188(3) Uani d . 1
C C4 0.51906(7) 0.2092(2) 0.56816(14) 0.0204(3) Uani d . 1
C C5 0.52305(7) 0.2761(2) 0.46731(14) 0.0220(3) Uani d . 1
H H5 0.4905 0.3437 0.4106 0.026 Uiso calc R 1
C C6 0.57402(7) 0.2450(2) 0.44867(13) 0.0217(4) Uani d . 1
H H6A 0.5761 0.2895 0.3785 0.026 Uiso calc R 1
C C7 0.67428(7) 0.1048(2) 0.50480(13) 0.0193(3) Uani d . 1
C C8 0.73631(7) 0.0819(2) 0.60007(13) 0.0194(3) Uani d . 1
C C9 0.77717(7) -0.0204(2) 0.57393(14) 0.0232(4) Uani d . 1
H H9 0.7649 -0.072 0.497 0.028 Uiso calc R 1
C C10 0.83534(7) -0.0471(2) 0.65921(15) 0.0268(4) Uani d . 1
H H10 0.8629 -0.118 0.6413 0.032 Uiso calc R 1
C C11 0.85344(7) 0.0300(2) 0.77117(15) 0.0273(4) Uani d . 1
H H11 0.8932 0.0102 0.8302 0.033 Uiso calc R 1
C C12 0.81387(7) 0.1355(2) 0.79721(14) 0.0248(4) Uani d . 1
H H12 0.8268 0.1901 0.8735 0.03 Uiso calc R 1
C C13 0.75534(7) 0.1618(2) 0.71223(13) 0.0210(3) Uani d . 1
H H13 0.7282 0.2342 0.7303 0.025 Uiso calc R 1
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C3 O2 H2 108.9(11)
C4 O3 H3 110.4(11)
C6 C1 C2 119.11(14)
C6 C1 C7 118.99(13)
C2 C1 C7 121.70(13)
C3 C2 C1 120.25(14)
C3 C2 H2A 119.9
C1 C2 H2A 119.9
O2 C3 C2 122.86(14)
O2 C3 C4 116.77(13)
C2 C3 C4 120.37(14)
O3 C4 C5 118.92(14)
O3 C4 C3 121.60(14)
C5 C4 C3 119.47(14)
C6 C5 C4 120.38(14)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 C1 120.41(14)
C5 C6 H6A 119.8
C1 C6 H6A 119.8
O1 C7 C1 119.47(13)
O1 C7 C8 118.60(13)
C1 C7 C8 121.91(12)
C9 C8 C13 119.30(14)
C9 C8 C7 117.89(13)
C13 C8 C7 122.79(14)
C10 C9 C8 120.44(15)
C10 C9 H9 119.8
C8 C9 H9 119.8
C9 C10 C11 119.76(15)
C9 C10 H10 120.1
C11 C10 H10 120.1
C12 C11 C10 120.36(15)
C12 C11 H11 119.8
C10 C11 H11 119.8
C11 C12 C13 120.10(15)
C11 C12 H12 119.9
C13 C12 H12 119.9
C12 C13 C8 119.99(15)
C12 C13 H13 120
C8 C13 H13 120
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2373(18)
O2 C3 1.3675(18)
O2 H2 0.94(2)
O3 C4 1.3571(18)
O3 H3 0.94(2)
C1 C6 1.394(2)
C1 C2 1.397(2)
C1 C7 1.478(2)
C2 C3 1.378(2)
C2 H2A 0.95
C3 C4 1.393(2)
C4 C5 1.385(2)
C5 C6 1.380(2)
C5 H5 0.95
C6 H6A 0.95
C7 C8 1.487(2)
C8 C9 1.395(2)
C8 C13 1.396(2)
C9 C10 1.382(2)
C9 H9 0.95
C10 C11 1.388(2)
C10 H10 0.95
C11 C12 1.382(2)
C11 H11 0.95
C12 C13 1.386(2)
C12 H12 0.95
C13 H13 0.95
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H2 O1 6_556 0.94(2) 1.71(2) 2.6391(16) 171.7(18)
O3 H3 O2 2_656 0.94(2) 1.91(2) 2.8149(16) 159.6(16)
C2 H2A O1 6_556 0.95 2.56 3.2309(18) 128.1
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
C6 C1 C2 C3 0.6(2)
C7 C1 C2 C3 -174.22(14)
C1 C2 C3 O2 179.45(14)
C1 C2 C3 C4 -0.1(2)
O2 C3 C4 O3 0.2(2)
C2 C3 C4 O3 179.83(14)
O2 C3 C4 C5 179.46(14)
C2 C3 C4 C5 -0.9(2)
O3 C4 C5 C6 -179.18(14)
C3 C4 C5 C6 1.6(2)
C4 C5 C6 C1 -1.1(2)
C2 C1 C6 C5 0.1(2)
C7 C1 C6 C5 174.99(14)
C6 C1 C7 O1 -30.3(2)
C2 C1 C7 O1 144.53(15)
C6 C1 C7 C8 151.66(14)
C2 C1 C7 C8 -33.5(2)
O1 C7 C8 C9 -20.9(2)
C1 C7 C8 C9 157.17(14)
O1 C7 C8 C13 157.44(15)
C1 C7 C8 C13 -24.5(2)
C13 C8 C9 C10 2.0(2)
C7 C8 C9 C10 -179.63(14)
C8 C9 C10 C11 -0.7(2)
C9 C10 C11 C12 -0.9(2)
C10 C11 C12 C13 1.4(2)
C11 C12 C13 C8 -0.1(2)
C9 C8 C13 C12 -1.5(2)
C7 C8 C13 C12 -179.88(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 145364
