#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/48/1504823.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_1504823
loop_
_publ_author_name
'Shukla, Ruchi'
'Wadumethrige, Shriya H.'
'Lindeman, Sergey V.'
'Rathore, Rajendra'
_publ_section_title
;
 Synthesis, electronic properties, and X-ray structural characterization
 of tetrarylbenzo[1,2-b:4,5-b']difuran cation radicals.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3587
_journal_page_last               3590
_journal_paper_doi               10.1021/ol801356e
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C34 H22 O2'
_chemical_formula_weight         462.52
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.7300(10)
_cell_angle_beta                 106.4600(10)
_cell_angle_gamma                95.153(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5994(9)
_cell_length_b                   10.9712(11)
_cell_length_c                   11.9451(12)
_cell_measurement_reflns_used    5683
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2
_cell_volume                     1196.2(2)
_computing_cell_refinement       'SAINT v7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 v1.0-27 (Bruker, 2005)'
_computing_data_reduction        'SADABS-2004/1 (Bruker, 2005)'
_computing_molecular_graphics    'XP v5.1 (Bruker, 1998)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'Bruker APEX2 CCD detector'
_diffrn_measurement_method       'omega scan'
_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  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            19414
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         31.95
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS. Program for empirical absorption correction of
 area-detector data. University of Goetingen. Germany. 
 Sheldrick, G. M. 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         7636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0488
_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)+(0.0768P)²+0.0593P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1386
_reflns_number_gt                5770
_reflns_number_total             7636
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801356e-file009.cif
_cod_data_source_block           rajf
_cod_database_code               1504823
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.81484(8) 0.35531(7) 0.31692(6) 0.02595(16) Uani 1 1 d .
C1 C 0.84494(11) 0.50398(10) 0.48501(9) 0.0244(2) Uani 1 1 d .
H1A H 0.7432 0.5050 0.4743 0.037 Uiso 1 1 calc R
C2 C 0.89950(11) 0.43248(9) 0.41173(9) 0.0234(2) Uani 1 1 d .
C3 C 1.04839(11) 0.42512(9) 0.42361(9) 0.0229(2) Uani 1 1 d .
C4 C 1.05298(11) 0.33710(9) 0.32921(9) 0.0231(2) Uani 1 1 d .
C5 C 0.91044(11) 0.29768(9) 0.26916(9) 0.0239(2) Uani 1 1 d .
C11 C 0.83791(11) 0.20662(9) 0.16997(9) 0.0240(2) Uani 1 1 d .
C12 C 0.89853(13) 0.09866(10) 0.15223(11) 0.0322(2) Uani 1 1 d .
H12A H 0.9899 0.0845 0.2037 0.039 Uiso 1 1 calc R
C13 C 0.82544(14) 0.01207(11) 0.05955(11) 0.0364(3) Uani 1 1 d .
H13A H 0.8673 -0.0611 0.0475 0.044 Uiso 1 1 calc R
C14 C 0.69229(13) 0.03154(11) -0.01534(11) 0.0354(3) Uani 1 1 d .
H14A H 0.6425 -0.0284 -0.0783 0.042 Uiso 1 1 calc R
C15 C 0.63136(12) 0.13832(11) 0.00131(10) 0.0319(2) Uani 1 1 d .
H15A H 0.5398 0.1517 -0.0504 0.038 Uiso 1 1 calc R
C16 C 0.70375(11) 0.22585(10) 0.09337(9) 0.0268(2) Uani 1 1 d .
H16A H 0.6618 0.2992 0.1043 0.032 Uiso 1 1 calc R
C21 C 1.18695(11) 0.30404(9) 0.30413(9) 0.0231(2) Uani 1 1 d .
C22 C 1.30741(11) 0.28309(10) 0.39532(10) 0.0284(2) Uani 1 1 d .
H22A H 1.3012 0.2872 0.4734 0.034 Uiso 1 1 calc R
C23 C 1.43616(12) 0.25634(11) 0.37325(11) 0.0352(3) Uani 1 1 d .
H23A H 1.5178 0.2429 0.4362 0.042 Uiso 1 1 calc R
C24 C 1.44609(13) 0.24914(11) 0.25990(12) 0.0366(3) Uani 1 1 d .
H24A H 1.5339 0.2298 0.2447 0.044 Uiso 1 1 calc R
C25 C 1.32717(13) 0.27035(11) 0.16837(11) 0.0339(3) Uani 1 1 d .
H25A H 1.3340 0.2662 0.0904 0.041 Uiso 1 1 calc R
C26 C 1.19881(12) 0.29753(10) 0.19006(10) 0.0282(2) Uani 1 1 d .
H26A H 1.1180 0.3119 0.1268 0.034 Uiso 1 1 calc R
O2 O 0.75873(8) 0.52287(7) 0.07047(7) 0.02984(18) Uani 1 1 d .
C6 C 0.87295(12) 0.41291(10) -0.05774(9) 0.0274(2) Uani 1 1 d .
H6A H 0.7887 0.3567 -0.0950 0.041 Uiso 1 1 calc R
C7 C 0.87529(11) 0.50294(10) 0.02896(9) 0.0267(2) Uani 1 1 d .
C8 C 0.99592(12) 0.58940(9) 0.08664(9) 0.0266(2) Uani 1 1 d .
C9 C 0.94794(12) 0.66549(10) 0.16915(9) 0.0275(2) Uani 1 1 d .
C10 C 0.80542(12) 0.62215(10) 0.15507(10) 0.0287(2) Uani 1 1 d .
C31 C 0.69311(12) 0.65906(11) 0.20740(10) 0.0305(2) Uani 1 1 d .
C32 C 0.58379(13) 0.57132(12) 0.21778(11) 0.0359(3) Uani 1 1 d .
H32A H 0.5829 0.4878 0.1907 0.043 Uiso 1 1 calc R
C33 C 0.47687(14) 0.60438(13) 0.26701(12) 0.0410(3) Uani 1 1 d .
H33A H 0.4042 0.5435 0.2747 0.049 Uiso 1 1 calc R
C34 C 0.47553(14) 0.72589(14) 0.30498(11) 0.0424(3) Uani 1 1 d .
H34A H 0.4016 0.7488 0.3382 0.051 Uiso 1 1 calc R
C35 C 0.58254(16) 0.81413(13) 0.29436(11) 0.0429(3) Uani 1 1 d .
H35A H 0.5813 0.8977 0.3200 0.051 Uiso 1 1 calc R
C36 C 0.69145(14) 0.78166(11) 0.24662(11) 0.0367(3) Uani 1 1 d .
H36A H 0.7650 0.8427 0.2406 0.044 Uiso 1 1 calc R
C41 C 1.04012(12) 0.76484(10) 0.25433(10) 0.0286(2) Uani 1 1 d .
C42 C 1.12828(12) 0.85302(10) 0.21873(11) 0.0313(2) Uani 1 1 d .
H42A H 1.1293 0.8489 0.1393 0.038 Uiso 1 1 calc R
C43 C 1.21472(13) 0.94693(11) 0.29862(12) 0.0381(3) Uani 1 1 d .
H43A H 1.2736 1.0071 0.2734 0.046 Uiso 1 1 calc R
C44 C 1.21534(16) 0.95304(13) 0.41425(13) 0.0474(3) Uani 1 1 d .
H44A H 1.2744 1.0174 0.4686 0.057 Uiso 1 1 calc R
C45 C 1.12977(18) 0.86519(14) 0.45112(12) 0.0516(4) Uani 1 1 d .
H45A H 1.1306 0.8691 0.5310 0.062 Uiso 1 1 calc R
C46 C 1.04297(16) 0.77157(12) 0.37178(11) 0.0413(3) Uani 1 1 d .
H46A H 0.9848 0.7114 0.3978 0.050 Uiso 1 1 calc R
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 O1 C5 106.60(7) . .
C2 C1 C3 114.56(9) . 2_766
O1 C2 C1 124.49(9) . .
O1 C2 C3 109.89(8) . .
C1 C2 C3 125.60(9) . .
C1 C3 C2 119.82(9) 2_766 .
C1 C3 C4 134.13(9) 2_766 .
C2 C3 C4 106.05(8) . .
C5 C4 C3 105.93(9) . .
C5 C4 C21 128.88(9) . .
C3 C4 C21 125.15(9) . .
C4 C5 O1 111.51(8) . .
C4 C5 C11 134.56(9) . .
O1 C5 C11 113.89(8) . .
C16 C11 C12 119.12(9) . .
C16 C11 C5 119.71(9) . .
C12 C11 C5 121.15(9) . .
C13 C12 C11 120.03(11) . .
C14 C13 C12 120.44(11) . .
C13 C14 C15 120.01(10) . .
C14 C15 C16 120.07(11) . .
C15 C16 C11 120.33(10) . .
C22 C21 C26 118.54(10) . .
C22 C21 C4 120.19(9) . .
C26 C21 C4 121.22(9) . .
C23 C22 C21 120.71(10) . .
C24 C23 C22 120.18(11) . .
C23 C24 C25 119.68(11) . .
C26 C25 C24 120.31(11) . .
C25 C26 C21 120.56(10) . .
C7 O2 C10 106.66(8) . .
C7 C6 C8 114.84(9) . 2_765
O2 C7 C6 124.83(9) . .
O2 C7 C8 109.90(9) . .
C6 C7 C8 125.26(10) . .
C6 C8 C7 119.90(10) 2_765 .
C6 C8 C9 134.21(10) 2_765 .
C7 C8 C9 105.89(10) . .
C10 C9 C8 106.12(9) . .
C10 C9 C41 128.22(10) . .
C8 C9 C41 125.58(10) . .
C9 C10 O2 111.42(10) . .
C9 C10 C31 134.21(10) . .
O2 C10 C31 114.36(9) . .
C32 C31 C36 118.65(11) . .
C32 C31 C10 120.03(10) . .
C36 C31 C10 121.32(11) . .
C33 C32 C31 120.87(12) . .
C34 C33 C32 120.12(13) . .
C33 C34 C35 119.66(12) . .
C34 C35 C36 120.66(12) . .
C35 C36 C31 120.03(12) . .
C46 C41 C42 118.61(11) . .
C46 C41 C9 121.03(10) . .
C42 C41 C9 120.35(10) . .
C43 C42 C41 120.47(11) . .
C44 C43 C42 120.24(12) . .
C43 C44 C45 119.90(12) . .
C44 C45 C46 120.13(13) . .
C45 C46 C41 120.64(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.3748(11) .
O1 C5 1.3861(12) .
C1 C2 1.3784(14) .
C1 C3 1.3993(14) 2_766
C2 C3 1.4060(14) .
C3 C1 1.3993(14) 2_766
C3 C4 1.4492(14) .
C4 C5 1.3678(14) .
C4 C21 1.4708(14) .
C5 C11 1.4629(13) .
C11 C16 1.3952(15) .
C11 C12 1.3955(15) .
C12 C13 1.3869(15) .
C13 C14 1.3804(18) .
C14 C15 1.3830(18) .
C15 C16 1.3871(15) .
C21 C22 1.3939(15) .
C21 C26 1.3970(15) .
C22 C23 1.3867(15) .
C23 C24 1.3816(18) .
C24 C25 1.3879(18) .
C25 C26 1.3824(16) .
O2 C7 1.3747(13) .
O2 C10 1.3860(13) .
C6 C7 1.3778(15) .
C6 C8 1.3982(15) 2_765
C7 C8 1.4075(14) .
C8 C6 1.3983(15) 2_765
C8 C9 1.4490(16) .
C9 C10 1.3669(15) .
C9 C41 1.4760(15) .
C10 C31 1.4644(16) .
C31 C32 1.3968(17) .
C31 C36 1.3982(17) .
C32 C33 1.3827(17) .
C33 C34 1.382(2) .
C34 C35 1.386(2) .
C35 C36 1.3868(19) .
C41 C46 1.3925(17) .
C41 C42 1.3941(16) .
C42 C43 1.3894(16) .
C43 C44 1.377(2) .
C44 C45 1.384(2) .
C45 C46 1.3855(18) .
