#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/82/4108247.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_4108247
loop_
_publ_author_name
'Igor V. Alabugin'
'Kerry Gilmore'
'Satish Patil'
'Mariappan Manoharan'
'Serguei V. Kovalenko'
'Ronald J. Clark'
'Ion Ghiviriga'
_publ_section_title
;
 Radical Cascade Transformations of Tris(o-aryleneethynylenes) into
 Substituted Benzo[a]indeno[2,1-c]fluorenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11535
_journal_page_last               11545
_journal_paper_doi               10.1021/ja8038213
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C32 H22'
_chemical_formula_sum            'C32 H22'
_chemical_formula_weight         406.50
_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                90.00
_cell_angle_beta                 116.4720(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.8728(9)
_cell_length_b                   10.6829(9)
_cell_length_c                   10.8760(9)
_cell_measurement_reflns_used    5340
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.83
_cell_volume                     1130.83(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15158
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_correction_T_min  0.9683
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_meas      0
_exptl_crystal_description       Plate
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0567
_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)+(0.0772P)²+0.3355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1518
_reflns_number_gt                2694
_reflns_number_total             2822
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8038213-file003.cif
_cod_data_source_block           igor41
_cod_original_sg_symbol_Hall     -P2ybc
_cod_database_code               4108247
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
C1 C 0.71803(17) 0.15938(18) 0.0554(2) 0.0509(4) Uani 1 1 d .
H1A H 0.6982 0.2007 -0.0320 0.076 Uiso 1 1 calc R
H1B H 0.7224 0.0686 0.0448 0.076 Uiso 1 1 calc R
H1C H 0.8064 0.1893 0.1265 0.076 Uiso 1 1 calc R
C2 C 0.60593(14) 0.18948(14) 0.09655(15) 0.0343(3) Uani 1 1 d .
C3 C 0.56246(16) 0.10234(14) 0.16300(17) 0.0404(4) Uani 1 1 d .
H3 H 0.6037 0.0218 0.1825 0.048 Uiso 1 1 calc R
C4 C 0.46007(15) 0.13012(13) 0.20166(16) 0.0358(3) Uani 1 1 d .
H4 H 0.4325 0.0688 0.2476 0.043 Uiso 1 1 calc R
C5 C 0.39733(12) 0.24744(12) 0.17352(12) 0.0255(3) Uani 1 1 d .
C6 C 0.43993(13) 0.33537(12) 0.10556(14) 0.0300(3) Uani 1 1 d .
H6 H 0.3981 0.4157 0.0848 0.036 Uiso 1 1 calc R
C7 C 0.54282(14) 0.30624(14) 0.06822(15) 0.0348(3) Uani 1 1 d .
H7 H 0.5708 0.3673 0.0223 0.042 Uiso 1 1 calc R
C8 C 0.28898(12) 0.27818(12) 0.20931(12) 0.0267(3) Uani 1 1 d .
C9 C 0.19547(12) 0.30920(11) 0.23248(12) 0.0252(3) Uani 1 1 d .
C10 C 0.08454(12) 0.35036(11) 0.25913(11) 0.0233(3) Uani 1 1 d .
C11 C 0.07107(13) 0.30674(13) 0.37373(12) 0.0289(3) Uani 1 1 d .
H11 H 0.1348 0.2471 0.4330 0.035 Uiso 1 1 calc R
C12 C -0.03365(15) 0.34917(14) 0.40198(14) 0.0342(3) Uani 1 1 d .
H12 H -0.0420 0.3181 0.4798 0.041 Uiso 1 1 calc R
C13 C -0.12624(15) 0.43672(14) 0.31722(15) 0.0357(3) Uani 1 1 d .
H13 H -0.1969 0.4670 0.3380 0.043 Uiso 1 1 calc R
C14 C -0.11636(14) 0.48039(13) 0.20207(14) 0.0316(3) Uani 1 1 d .
H14 H -0.1811 0.5398 0.1438 0.038 Uiso 1 1 calc R
C15 C -0.01193(12) 0.43788(11) 0.17076(12) 0.0248(3) Uani 1 1 d .
C16 C -0.00290(13) 0.48201(12) 0.05055(13) 0.0278(3) Uani 1 1 d .
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'
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
C2 C1 H1A 109.5 .
C2 C1 H1B 109.5 .
H1A C1 H1B 109.5 .
C2 C1 H1C 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
C3 C2 C7 117.99(12) .
C3 C2 C1 121.37(14) .
C7 C2 C1 120.64(14) .
C2 C3 C4 121.44(13) .
C2 C3 H3 119.3 .
C4 C3 H3 119.3 .
C3 C4 C5 120.43(13) .
C3 C4 H4 119.8 .
C5 C4 H4 119.8 .
C4 C5 C6 118.41(11) .
C4 C5 C8 121.81(12) .
C6 C5 C8 119.76(11) .
C7 C6 C5 120.40(12) .
C7 C6 H6 119.8 .
C5 C6 H6 119.8 .
C6 C7 C2 121.33(13) .
C6 C7 H7 119.3 .
C2 C7 H7 119.3 .
C9 C8 C5 175.85(13) .
C8 C9 C10 178.13(13) .
C11 C10 C15 119.05(10) .
C11 C10 C9 120.75(11) .
C15 C10 C9 120.19(10) .
C12 C11 C10 120.87(12) .
C12 C11 H11 119.6 .
C10 C11 H11 119.6 .
C11 C12 C13 120.08(11) .
C11 C12 H12 120.0 .
C13 C12 H12 120.0 .
C12 C13 C14 120.27(12) .
C12 C13 H13 119.9 .
C14 C13 H13 119.9 .
C13 C14 C15 120.63(12) .
C13 C14 H14 119.7 .
C15 C14 H14 119.7 .
C14 C15 C10 119.08(11) .
C14 C15 C16 120.55(11) .
C10 C15 C16 120.38(10) .
C16 C16 C15 179.1(2) 3_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.5088(18) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C3 1.384(2) .
C2 C7 1.390(2) .
C3 C4 1.3862(18) .
C3 H3 0.9500 .
C4 C5 1.3941(18) .
C4 H4 0.9500 .
C5 C6 1.3959(18) .
C5 C8 1.4339(16) .
C6 C7 1.3850(17) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 C9 1.1981(17) .
C9 C10 1.4296(16) .
C10 C11 1.3981(16) .
C10 C15 1.4140(17) .
C11 C12 1.3814(17) .
C11 H11 0.9500 .
C12 C13 1.382(2) .
C12 H12 0.9500 .
C13 C14 1.3848(18) .
C13 H13 0.9500 .
C14 C15 1.3986(16) .
C14 H14 0.9500 .
C15 C16 1.4338(16) .
C16 C16 1.193(2) 3_565
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
C7 C2 C3 C4 -0.6(2)
C1 C2 C3 C4 179.60(15)
C2 C3 C4 C5 0.4(2)
C3 C4 C5 C6 0.2(2)
C3 C4 C5 C8 178.55(13)
C4 C5 C6 C7 -0.4(2)
C8 C5 C6 C7 -178.88(12)
C5 C6 C7 C2 0.2(2)
C3 C2 C7 C6 0.3(2)
C1 C2 C7 C6 -179.89(13)
C15 C10 C11 C12 -0.8(2)
C9 C10 C11 C12 178.06(12)
C10 C11 C12 C13 -0.6(2)
C11 C12 C13 C14 1.4(2)
C12 C13 C14 C15 -0.8(2)
C13 C14 C15 C10 -0.6(2)
C13 C14 C15 C16 179.21(13)
C11 C10 C15 C14 1.36(19)
C9 C10 C15 C14 -177.50(12)
C11 C10 C15 C16 -178.44(12)
C9 C10 C15 C16 2.70(18)
