#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/48/1504825.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_1504825
loop_
_publ_author_name
'Zhang, Hongyu'
'Wakamiya, Atsushi'
'Yamaguchi, Shigehiro'
_publ_section_title
;
 Highly electron-donating 3,3'-diaryl-1,1'-bi(isobenzofuran)s synthesized
 by photochemical exocyclic [2 + 2 + 2] cycloaddition.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3591
_journal_page_last               3594
_journal_paper_doi               10.1021/ol801358c
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C30 H18 F6 O2'
_chemical_formula_weight         524.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                90.000
_cell_angle_beta                 102.295(11)
_cell_angle_gamma                90.000
_cell_formula_units_Z            2
_cell_length_a                   12.13(2)
_cell_length_b                   5.926(11)
_cell_length_c                   15.66(3)
_cell_measurement_reflns_used    2747
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      31.5050
_cell_measurement_theta_min      1.9357
_cell_volume                     1100(3)
_computing_molecular_graphics    'ORTEP 3 for windows'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
;
Saturn70 CCD (4x4 bin mode) with MicroMax-007

;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6548
_diffrn_reflns_theta_full        25.48
_diffrn_reflns_theta_max         25.48
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.860
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0898
_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)+(0.1919P)²+0.0590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2429
_refine_ls_wR_factor_ref         0.2751
_reflns_number_gt                1518
_reflns_number_total             2033
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801358c-file004.cif
_cod_data_source_block           comp2c
_cod_original_cell_volume        1100(4)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1504825
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
C20 C 0.2234(3) -0.0108(5) 0.60210(19) 0.0248(8) Uani 1 1 d .
O1 O 0.11353(18) 0.3027(4) 0.53502(14) 0.0261(6) Uani 1 1 d .
C22 C 0.1187(3) 0.1150(5) 0.5883(2) 0.0244(8) Uani 1 1 d .
C23 C -0.0535(3) 0.2827(5) 0.57620(19) 0.0244(8) Uani 1 1 d .
C24 C -0.0273(3) -0.0607(6) 0.6695(2) 0.0270(8) Uani 1 1 d .
H1 H 0.0177 -0.1824 0.6970 0.032 Uiso 1 1 calc R
C25 C 0.2336(3) -0.2264(6) 0.64066(19) 0.0261(8) Uani 1 1 d .
H2 H 0.1706 -0.2920 0.6583 0.031 Uiso 1 1 calc R
C26 C 0.3349(3) -0.3445(6) 0.6532(2) 0.0257(8) Uani 1 1 d .
H3 H 0.3407 -0.4896 0.6796 0.031 Uiso 1 1 calc R
C27 C 0.0093(3) 0.4032(5) 0.5271(2) 0.0265(8) Uani 1 1 d .
F1 F 0.53184(18) -0.5872(4) 0.66406(19) 0.0543(8) Uani 1 1 d .
C28 C 0.4188(3) -0.0391(6) 0.5880(2) 0.0268(8) Uani 1 1 d .
H4 H 0.4818 0.0249 0.5698 0.032 Uiso 1 1 calc R
F2 F 0.61681(18) -0.2818(4) 0.70419(17) 0.0594(9) Uani 1 1 d .
C12 C -0.1648(3) 0.3097(6) 0.59091(19) 0.0257(8) Uani 1 1 d .
H5 H -0.2106 0.4326 0.5656 0.031 Uiso 1 1 calc R
C13 C -0.2045(3) 0.1562(6) 0.6420(2) 0.0298(8) Uani 1 1 d .
H6 H -0.2787 0.1730 0.6519 0.036 Uiso 1 1 calc R
C29 C -0.1362(3) -0.0309(6) 0.6811(2) 0.0289(8) Uani 1 1 d .
H7 H -0.1666 -0.1361 0.7157 0.035 Uiso 1 1 calc R
F3 F 0.5836(2) -0.3745(6) 0.56974(15) 0.0700(10) Uani 1 1 d .
C30 C 0.4285(3) -0.2502(6) 0.6269(2) 0.0264(8) Uani 1 1 d .
C17 C 0.5380(3) -0.3740(6) 0.6409(2) 0.0280(8) Uani 1 1 d .
C31 C 0.0162(3) 0.0957(5) 0.6152(2) 0.0241(8) Uani 1 1 d .
C32 C 0.3186(3) 0.0791(6) 0.5754(2) 0.0281(8) Uani 1 1 d .
H8 H 0.3136 0.2233 0.5484 0.034 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'
F F 0.0171 0.0103 '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_3
C25 C20 C32 117.8(3) .
C25 C20 C22 121.7(3) .
C32 C20 C22 120.5(3) .
C27 O1 C22 108.9(3) .
O1 C22 C31 108.5(3) .
O1 C22 C20 115.5(3) .
C31 C22 C20 136.0(3) .
C27 C23 C12 132.9(3) .
C27 C23 C31 106.7(3) .
C12 C23 C31 120.4(3) .
C29 C24 C31 118.6(3) .
C26 C25 C20 120.8(3) .
C25 C26 C30 120.2(3) .
O1 C27 C23 109.2(3) .
O1 C27 C27 115.4(4) 3_566
C23 C27 C27 135.4(4) 3_566
C32 C28 C30 120.7(3) .
C13 C12 C23 119.0(3) .
C12 C13 C29 121.3(3) .
C24 C29 C13 121.5(3) .
C28 C30 C26 119.3(3) .
C28 C30 C17 119.9(3) .
C26 C30 C17 120.8(3) .
F1 C17 F2 105.1(3) .
F1 C17 F3 106.4(3) .
F2 C17 F3 105.0(3) .
F1 C17 C30 114.2(3) .
F2 C17 C30 112.4(3) .
F3 C17 C30 113.0(3) .
C22 C31 C24 134.0(3) .
C22 C31 C23 106.7(3) .
C24 C31 C23 119.3(3) .
C28 C32 C20 121.1(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C20 C25 1.407(5) .
C20 C32 1.413(5) .
C20 C22 1.449(5) .
O1 C27 1.380(5) .
O1 C22 1.383(4) .
C22 C31 1.400(5) .
C23 C27 1.389(5) .
C23 C12 1.427(5) .
C23 C31 1.447(5) .
C24 C29 1.382(5) .
C24 C31 1.433(5) .
C25 C26 1.391(5) .
C26 C30 1.404(5) .
C27 C27 1.416(7) 3_566
F1 C17 1.321(5) .
C28 C32 1.380(5) .
C28 C30 1.385(5) .
F2 C17 1.338(4) .
C12 C13 1.365(5) .
C13 C29 1.441(5) .
F3 C17 1.345(5) .
C30 C17 1.492(5) .
