#------------------------------------------------------------------------------
#$Date: 2016-02-20 17:35:30 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/21/2212102.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_2212102
loop_
_publ_author_name
'Hong-Min Zhao'
'Jing-Jun Liu'
'Jian Zhang'
'Shu-Ying Zhang'
'Xu Li'
_publ_section_title
;
 3,3'-Dibenzyl-3,3'-dihydroxy-[2,2'-bi-1H-indene]-1,1'-dione
;
_journal_coeditor_code           CI2275
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o750
_journal_page_last               o751
_journal_paper_doi               10.1107/S1600536807001535
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C32 H24 O4'
_chemical_formula_moiety         'C32 H24 O4'
_chemical_formula_sum            'C32 H24 O4'
_chemical_formula_weight         472.51
_chemical_name_systematic
;
3,3'-Dibenzyl-3,3'-dihydroxy-[2,2'-bi-1H-indene]-1,1'-dione
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.576(6)
_cell_length_b                   9.611(4)
_cell_length_c                   16.139(6)
_cell_measurement_reflns_used    2620
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      21.41
_cell_measurement_theta_min      2.62
_cell_volume                     2416.0(16)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12722
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         2.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0426
_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)+(0.0521P)²+0.4227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1209
_reflns_number_gt                1482
_reflns_number_total             2462
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2275.cif
_cod_data_source_block           I
_cod_original_cell_volume        2416.1(17)
_cod_database_code               2212102
_cod_database_fobs_code          2212102
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 0.65842(8) 0.57513(15) 0.45300(9) 0.0652(4) Uani d . 1
O O2 0.38464(8) 0.69523(17) 0.55169(9) 0.0574(4) Uani d . 1
H H2 0.3606(17) 0.605(3) 0.5552(17) 0.109(10) Uiso d . 1
C C1 0.59950(11) 0.6272(2) 0.49314(11) 0.0456(5) Uani d . 1
C C2 0.51514(10) 0.56101(18) 0.51526(10) 0.0401(4) Uani d . 1
C C3 0.46932(10) 0.66008(18) 0.57587(11) 0.0409(4) Uani d . 1
C C4 0.52364(11) 0.78932(18) 0.57118(11) 0.0431(5) Uani d . 1
C C5 0.50771(14) 0.9187(2) 0.60669(11) 0.0552(5) Uani d . 1
H H5 0.4568 0.9355 0.6350 0.066 Uiso calc R 1
C C6 0.56912(15) 1.0220(2) 0.59903(12) 0.0616(6) Uani d . 1
H H6 0.5596 1.1082 0.6235 0.074 Uiso calc R 1
C C7 0.64517(15) 0.9990(2) 0.55510(13) 0.0671(6) Uani d . 1
H H7 0.6850 1.0705 0.5496 0.080 Uiso calc R 1
C C8 0.66163(13) 0.8702(2) 0.51966(12) 0.0569(5) Uani d . 1
H H8 0.7126 0.8530 0.4915 0.068 Uiso calc R 1
C C9 0.59926(11) 0.7679(2) 0.52776(11) 0.0451(5) Uani d . 1
C C10 0.46946(12) 0.6018(2) 0.66545(11) 0.0483(5) Uani d . 1
H H10A 0.4412 0.6684 0.7014 0.058 Uiso calc R 1
H H10B 0.4358 0.5168 0.6664 0.058 Uiso calc R 1
C C11 0.55721(12) 0.5708(2) 0.70053(11) 0.0478(5) Uani d . 1
C C12 0.59917(14) 0.4470(2) 0.68168(12) 0.0597(6) Uani d . 1
H H12 0.5727 0.3826 0.6471 0.072 Uiso calc R 1
C C13 0.67921(17) 0.4186(3) 0.71337(15) 0.0814(8) Uani d . 1
H H13 0.7069 0.3361 0.6995 0.098 Uiso calc R 1
C C14 0.71836(18) 0.5122(4) 0.76569(17) 0.0957(9) Uani d . 1
H H14 0.7721 0.4922 0.7877 0.115 Uiso calc R 1
C C15 0.67810(19) 0.6358(3) 0.78554(15) 0.0842(8) Uani d . 1
H H15 0.7045 0.6989 0.8210 0.101 Uiso calc R 1
C C16 0.59848(15) 0.6649(2) 0.75245(12) 0.0632(6) Uani d . 1
H H16 0.5719 0.7489 0.7651 0.076 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 0.0000 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle
C3 O2 H2 . 97.7(17)
O1 C1 C9 . 125.41(17)
O1 C1 C2 . 127.22(18)
C9 C1 C2 . 107.37(15)
C2 C2 C1 5_666 125.7(2)
C2 C2 C3 5_666 127.1(2)
C1 C2 C3 . 107.10(15)
O2 C3 C4 . 108.23(15)
O2 C3 C2 . 113.83(14)
C4 C3 C2 . 102.58(14)
O2 C3 C10 . 110.15(14)
C4 C3 C10 . 110.15(14)
C2 C3 C10 . 111.59(14)
C9 C4 C5 . 119.50(18)
C9 C4 C3 . 112.37(15)
C5 C4 C3 . 128.08(17)
C6 C5 C4 . 118.75(19)
C6 C5 H5 . 120.6
C4 C5 H5 . 120.6
C5 C6 C7 . 121.2(2)
C5 C6 H6 . 119.4
C7 C6 H6 . 119.4
C8 C7 C6 . 120.4(2)
C8 C7 H7 . 119.8
C6 C7 H7 . 119.8
C7 C8 C9 . 117.6(2)
C7 C8 H8 . 121.2
C9 C8 H8 . 121.2
C4 C9 C8 . 122.49(18)
C4 C9 C1 . 109.42(16)
C8 C9 C1 . 128.08(18)
C11 C10 C3 . 114.99(14)
C11 C10 H10A . 108.5
C3 C10 H10A . 108.5
C11 C10 H10B . 108.5
C3 C10 H10B . 108.5
H10A C10 H10B . 107.5
C16 C11 C12 . 118.09(19)
C16 C11 C10 . 121.10(19)
C12 C11 C10 . 120.81(18)
C13 C12 C11 . 121.0(2)
C13 C12 H12 . 119.5
C11 C12 H12 . 119.5
C12 C13 C14 . 120.0(3)
C12 C13 H13 . 120.0
C14 C13 H13 . 120.0
C13 C14 C15 . 120.2(2)
C13 C14 H14 . 119.9
C15 C14 H14 . 119.9
C16 C15 C14 . 119.6(2)
C16 C15 H15 . 120.2
C14 C15 H15 . 120.2
C15 C16 C11 . 121.1(2)
C15 C16 H16 . 119.4
C11 C16 H16 . 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.230(2)
O2 C3 . 1.416(2)
O2 H2 . 0.94(3)
C1 C9 . 1.463(3)
C1 C2 . 1.503(2)
C2 C2 5_666 1.357(3)
C2 C3 . 1.540(2)
C3 C4 . 1.505(2)
C3 C10 . 1.551(3)
C4 C9 . 1.386(2)
C4 C5 . 1.392(3)
C5 C6 . 1.384(3)
C5 H5 . 0.93
C6 C7 . 1.398(3)
C6 H6 . 0.93
C7 C8 . 1.387(3)
C7 H7 . 0.93
C8 C9 . 1.388(3)
C8 H8 . 0.93
C10 C11 . 1.509(3)
C10 H10A . 0.97
C10 H10B . 0.97
C11 C16 . 1.391(3)
C11 C12 . 1.391(3)
C12 C13 . 1.375(3)
C12 H12 . 0.93
C13 C14 . 1.377(4)
C13 H13 . 0.93
C14 C15 . 1.380(4)
C14 H14 . 0.93
C15 C16 . 1.379(3)
C15 H15 . 0.93
C16 H16 . 0.93
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 5_666 0.94(3) 1.76(3) 2.685(2) 164(3)
C5 H5 Cg1 3_656 0.93 2.79 3.640(3) 153
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
O1 C1 C2 C2 . 5_666 -9.8(3)
C9 C1 C2 C2 . 5_666 169.7(2)
O1 C1 C2 C3 . . 172.19(18)
C9 C1 C2 C3 . . -8.26(18)
C2 C2 C3 O2 5_666 . -50.7(3)
C1 C2 C3 O2 . . 127.22(16)
C2 C2 C3 C4 5_666 . -167.4(2)
C1 C2 C3 C4 . . 10.54(17)
C2 C2 C3 C10 5_666 . 74.7(3)
C1 C2 C3 C10 . . -107.35(16)
O2 C3 C4 C9 . . -130.34(16)
C2 C3 C4 C9 . . -9.72(18)
C10 C3 C4 C9 . . 109.19(16)
O2 C3 C4 C5 . . 52.2(2)
C2 C3 C4 C5 . . 172.78(17)
C10 C3 C4 C5 . . -68.3(2)
C9 C4 C5 C6 . . -1.4(3)
C3 C4 C5 C6 . . 175.98(17)
C4 C5 C6 C7 . . 1.4(3)
C5 C6 C7 C8 . . -1.5(3)
C6 C7 C8 C9 . . 1.6(3)
C5 C4 C9 C8 . . 1.6(3)
C3 C4 C9 C8 . . -176.16(16)
C5 C4 C9 C1 . . -177.29(16)
C3 C4 C9 C1 . . 5.0(2)
C7 C8 C9 C4 . . -1.7(3)
C7 C8 C9 C1 . . 176.97(19)
O1 C1 C9 C4 . . -178.18(18)
C2 C1 C9 C4 . . 2.26(19)
O1 C1 C9 C8 . . 3.0(3)
C2 C1 C9 C8 . . -176.53(18)
O2 C3 C10 C11 . . -175.53(15)
C4 C3 C10 C11 . . -56.2(2)
C2 C3 C10 C11 . . 57.0(2)
C3 C10 C11 C16 . . 98.1(2)
C3 C10 C11 C12 . . -81.8(2)
C16 C11 C12 C13 . . -0.1(3)
C10 C11 C12 C13 . . 179.85(18)
C11 C12 C13 C14 . . 1.1(3)
C12 C13 C14 C15 . . -1.0(4)
C13 C14 C15 C16 . . -0.2(4)
C14 C15 C16 C11 . . 1.2(3)
C12 C11 C16 C15 . . -1.1(3)
C10 C11 C16 C15 . . 179.01(18)
