#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/27/1502744.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_1502744
loop_
_publ_author_name
'Schwerin, Andrew F.'
'Johnson, Justin C.'
'Smith, Millicent B.'
'Sreearunothai, Paiboon'
'Popović, Duska'
'Cerný, Jirí'
'Havlas, Zdenek'
'Paci, Irina'
'Akdag, Akin'
'MacLeod, Matthew K.'
'Chen, Xudong'
'David, Donald E.'
'Ratner, Mark A.'
'Miller, John R.'
'Nozik, Arthur J.'
'Michl, Josef'
_publ_section_title
;
 Toward designed singlet fission: electronic states and photophysics of
 1,3-diphenylisobenzofuran.
;
_journal_issue                   3
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              1457
_journal_page_last               1473
_journal_paper_doi               10.1021/jp907401t
_journal_volume                  114
_journal_year                    2010
_chemical_formula_sum            'C20 H14 O'
_chemical_formula_weight         270.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           13
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/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                 106.472(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8954(10)
_cell_length_b                   5.5486(4)
_cell_length_c                   20.0322(15)
_cell_measurement_temperature    147(2)
_cell_volume                     1374.51(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0806
_diffrn_reflns_av_sigmaI/netI    0.1235
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7265
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.9653
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0646
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0439P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1712
_reflns_number_gt                1889
_reflns_number_total             3089
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp907401t_si_002.cif
_cod_data_source_block           mm2105fm
_cod_database_code               1502744
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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
O1 O 0.29645(12) 0.4499(3) 0.35645(8) 0.0295(4) Uani 1 1 d .
C1 C 0.21935(18) 0.3018(4) 0.31473(11) 0.0287(5) Uani 1 1 d .
C2 C 0.20911(18) 0.3554(4) 0.24598(11) 0.0282(5) Uani 1 1 d .
C3 C 0.1425(2) 0.2656(4) 0.18156(12) 0.0329(6) Uani 1 1 d .
H3 H 0.0911 0.1421 0.1806 0.039 Uiso 1 1 calc R
C4 C 0.1537(2) 0.3598(4) 0.12145(12) 0.0343(6) Uani 1 1 d .
H4 H 0.1093 0.3011 0.0782 0.041 Uiso 1 1 calc R
C5 C 0.2308(2) 0.5454(5) 0.12172(12) 0.0363(6) Uani 1 1 d .
H5 H 0.2371 0.6049 0.0786 0.044 Uiso 1 1 calc R
C6 C 0.29488(19) 0.6385(4) 0.18168(12) 0.0320(6) Uani 1 1 d .
H6 H 0.3455 0.7620 0.1808 0.038 Uiso 1 1 calc R
C7 C 0.28491(17) 0.5476(4) 0.24623(11) 0.0274(5) Uani 1 1 d .
C8 C 0.33622(18) 0.5993(4) 0.31481(11) 0.0282(5) Uani 1 1 d .
C9 C 0.16473(19) 0.1807(4) 0.41887(12) 0.0322(6) Uani 1 1 d .
H9 H 0.1972 0.3233 0.4417 0.039 Uiso 1 1 calc R
C10 C 0.1146(2) 0.0197(5) 0.45328(13) 0.0373(6) Uani 1 1 d .
H10 H 0.1139 0.0519 0.4997 0.045 Uiso 1 1 calc R
C11 C 0.0658(2) -0.1866(4) 0.42005(13) 0.0370(6) Uani 1 1 d .
H11 H 0.0306 -0.2947 0.4433 0.044 Uiso 1 1 calc R
C12 C 0.0685(2) -0.2348(4) 0.35295(13) 0.0354(6) Uani 1 1 d .
H12 H 0.0352 -0.3767 0.3301 0.043 Uiso 1 1 calc R
C13 C 0.11944(19) -0.0774(4) 0.31877(12) 0.0308(5) Uani 1 1 d .
H13 H 0.1217 -0.1134 0.2728 0.037 Uiso 1 1 calc R
C14 C 0.16733(18) 0.1330(4) 0.35106(11) 0.0283(5) Uani 1 1 d .
C15 C 0.42146(18) 0.7646(4) 0.35135(12) 0.0300(5) Uani 1 1 d .
C16 C 0.44221(19) 0.9758(4) 0.31964(13) 0.0330(6) Uani 1 1 d .
H16 H 0.3989 1.0160 0.2742 0.040 Uiso 1 1 calc R
C17 C 0.5257(2) 1.1275(4) 0.35402(14) 0.0387(6) Uani 1 1 d .
H17 H 0.5396 1.2703 0.3318 0.046 Uiso 1 1 calc R
C18 C 0.5886(2) 1.0727(5) 0.42003(13) 0.0409(6) Uani 1 1 d .
H18 H 0.6462 1.1764 0.4432 0.049 Uiso 1 1 calc R
C19 C 0.5677(2) 0.8652(5) 0.45273(13) 0.0397(6) Uani 1 1 d .
H19 H 0.6099 0.8283 0.4987 0.048 Uiso 1 1 calc R
C20 C 0.4851(2) 0.7123(5) 0.41820(12) 0.0340(6) Uani 1 1 d .
H20 H 0.4718 0.5694 0.4405 0.041 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
C8 O1 C1 108.74(17)
O1 C1 C2 109.0(2)
O1 C1 C14 115.80(19)
C2 C1 C14 135.2(2)
C1 C2 C3 133.9(2)
C1 C2 C7 106.43(19)
C3 C2 C7 119.7(2)
C4 C3 C2 118.8(2)
C3 C4 C5 121.5(2)
C6 C5 C4 121.9(2)
C5 C6 C7 118.7(2)
C8 C7 C6 133.6(2)
C8 C7 C2 106.89(19)
C6 C7 C2 119.5(2)
O1 C8 C7 108.90(19)
O1 C8 C15 115.62(19)
C7 C8 C15 135.5(2)
C14 C9 C10 120.2(2)
C11 C10 C9 120.2(2)
C12 C11 C10 119.7(2)
C11 C12 C13 120.4(2)
C12 C13 C14 120.6(2)
C13 C14 C9 118.8(2)
C13 C14 C1 120.8(2)
C9 C14 C1 120.4(2)
C20 C15 C16 118.5(2)
C20 C15 C8 120.5(2)
C16 C15 C8 121.0(2)
C17 C16 C15 120.4(2)
C18 C17 C16 120.4(2)
C17 C18 C19 119.8(2)
C20 C19 C18 119.9(2)
C19 C20 C15 121.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.374(3)
O1 C1 1.375(3)
C1 C2 1.378(3)
C1 C14 1.461(3)
C2 C3 1.422(3)
C2 C7 1.445(3)
C3 C4 1.357(3)
C4 C5 1.430(4)
C5 C6 1.353(3)
C6 C7 1.427(3)
C7 C8 1.375(3)
C8 C15 1.459(3)
C9 C14 1.394(3)
C9 C10 1.394(3)
C10 C11 1.383(4)
C11 C12 1.380(4)
C12 C13 1.385(3)
C13 C14 1.392(3)
C15 C20 1.389(3)
C15 C16 1.395(3)
C16 C17 1.386(3)
C17 C18 1.375(4)
C18 C19 1.389(4)
C19 C20 1.383(3)
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
C8 O1 C1 C2 0.0(2)
C8 O1 C1 C14 -179.08(19)
O1 C1 C2 C3 -178.9(2)
C14 C1 C2 C3 -0.1(5)
O1 C1 C2 C7 0.1(3)
C14 C1 C2 C7 178.9(2)
C1 C2 C3 C4 -179.6(3)
C7 C2 C3 C4 1.5(3)
C2 C3 C4 C5 0.2(4)
C3 C4 C5 C6 -1.0(4)
C4 C5 C6 C7 0.1(4)
C5 C6 C7 C8 179.7(2)
C5 C6 C7 C2 1.6(3)
C1 C2 C7 C8 -0.1(3)
C3 C2 C7 C8 179.0(2)
C1 C2 C7 C6 178.4(2)
C3 C2 C7 C6 -2.4(3)
C1 O1 C8 C7 0.0(2)
C1 O1 C8 C15 -178.46(19)
C6 C7 C8 O1 -178.2(2)
C2 C7 C8 O1 0.1(2)
C6 C7 C8 C15 -0.2(5)
C2 C7 C8 C15 178.1(2)
C14 C9 C10 C11 -0.9(4)
C9 C10 C11 C12 1.1(4)
C10 C11 C12 C13 -0.2(4)
C11 C12 C13 C14 -0.9(4)
C12 C13 C14 C9 1.1(3)
C12 C13 C14 C1 -178.8(2)
C10 C9 C14 C13 -0.2(3)
C10 C9 C14 C1 179.7(2)
O1 C1 C14 C13 -156.7(2)
C2 C1 C14 C13 24.6(4)
O1 C1 C14 C9 23.4(3)
C2 C1 C14 C9 -155.3(3)
O1 C8 C15 C20 23.8(3)
C7 C8 C15 C20 -154.0(3)
O1 C8 C15 C16 -157.4(2)
C7 C8 C15 C16 24.8(4)
C20 C15 C16 C17 0.9(3)
C8 C15 C16 C17 -177.9(2)
C15 C16 C17 C18 -0.5(4)
C16 C17 C18 C19 -0.6(4)
C17 C18 C19 C20 1.4(4)
C18 C19 C20 C15 -0.9(4)
C16 C15 C20 C19 -0.2(4)
C8 C15 C20 C19 178.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 20348 ChemSpider
