#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:51:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180319 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/33/7153392.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_7153392
loop_
_publ_author_name
'Banide, Emilie V.'
'O'Connor, Crystal'
'Fortune, Natasha'
'Ortin, Yannick'
'Milosevic, Sandra'
'Müller-Bunz, Helge'
'McGlinchey, Michael J.'
_publ_section_title
;
 Syntheses, X-ray crystal structures and reactivity of fluorenylidene- and
 dibenzosuberenylidene-allenes: convenient precursors to
 dispirotetracenes, di-indenotetracenes and
 2-phenyl-11bH-dibenz[cd,h]azulene.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3997
_journal_page_last               4010
_journal_paper_doi               10.1039/c004868b
_journal_volume                  8
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C44 H26 F6, C6 H14'
_chemical_formula_sum            'C50 H40 F6'
_chemical_formula_weight         754.82
_chemical_name_systematic
;
?
;
_space_group_IT_number           45
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'I 2 -2c'
_symmetry_space_group_name_H-M   'I b a 2'
_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                   10.154(3)
_cell_length_b                   16.592(4)
_cell_length_c                   23.131(6)
_cell_measurement_reflns_used    1968
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.27
_cell_measurement_theta_min      2.35
_cell_volume                     3897.0(18)
_computing_cell_refinement       'Bruker SAINT'
_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      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9426
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9954
_exptl_absorpt_correction_T_min  0.7172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.064 before and 0.038 after
correction. The Ratio of minimum to maximum transmission is 0.720484.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1576
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
;
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         1976
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0526
_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)+(0.0916P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1361
_reflns_number_gt                1672
_reflns_number_total             1976
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c004868b.txt
_cod_data_source_block           mjm61(14)
_cod_original_cell_volume        3897.0(17)
_cod_database_code               7153392
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1, z+1/2'
'-x+1, y+1, 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 0.4336(3) 0.01668(17) 0.06649(14) 0.0163(7) Uani 1 1 d .
C3 C 0.3605(3) 0.06478(18) 0.10083(14) 0.0178(7) Uani 1 1 d .
C4 C 0.3968(3) 0.10288(19) 0.15604(15) 0.0183(7) Uani 1 1 d .
C5 C 0.5089(4) 0.09466(18) 0.19081(15) 0.0193(7) Uani 1 1 d .
H5 H 0.5778 0.0590 0.1800 0.023 Uiso 1 1 calc R
C6 C 0.5178(4) 0.13959(19) 0.24148(16) 0.0232(8) Uani 1 1 d .
H6 H 0.5931 0.1339 0.2655 0.028 Uiso 1 1 calc R
C7 C 0.4182(4) 0.1928(2) 0.25750(16) 0.0285(9) Uani 1 1 d .
H7 H 0.4255 0.2224 0.2925 0.034 Uiso 1 1 calc R
C8 C 0.3080(4) 0.2029(2) 0.22238(16) 0.0272(9) Uani 1 1 d .
H8 H 0.2408 0.2400 0.2328 0.033 Uiso 1 1 calc R
C9 C 0.2977(4) 0.1577(2) 0.17175(16) 0.0222(8) Uani 1 1 d .
C10 C 0.1936(4) 0.1560(2) 0.12823(15) 0.0202(8) Uani 1 1 d .
C11 C 0.0741(4) 0.1963(2) 0.12527(16) 0.0252(9) Uani 1 1 d .
H11 H 0.0503 0.2346 0.1540 0.030 Uiso 1 1 calc R
C12 C -0.0094(4) 0.1797(2) 0.07974(19) 0.0302(9) Uani 1 1 d .
H12 H -0.0909 0.2075 0.0768 0.036 Uiso 1 1 calc R
C13 C 0.0243(4) 0.1223(2) 0.03781(18) 0.0276(8) Uani 1 1 d .
H13 H -0.0348 0.1113 0.0070 0.033 Uiso 1 1 calc R
C14 C 0.1441(4) 0.0813(2) 0.04103(16) 0.0215(8) Uani 1 1 d .
H14 H 0.1663 0.0420 0.0128 0.026 Uiso 1 1 calc R
C15 C 0.2299(3) 0.09844(18) 0.08549(15) 0.0183(7) Uani 1 1 d .
C2 C 0.4226(3) 0.00565(18) 0.00108(14) 0.0182(7) Uani 1 1 d .
H2 H 0.3949 0.0563 -0.0189 0.022 Uiso 1 1 calc R
C16 C 0.3523(3) -0.06749(19) -0.02228(15) 0.0187(7) Uani 1 1 d .
C17 C 0.3405(3) -0.13822(19) 0.00904(14) 0.0178(7) Uani 1 1 d .
H17 H 0.3693 -0.1396 0.0481 0.021 Uiso 1 1 calc R
C18 C 0.2875(4) -0.2067(2) -0.01548(16) 0.0208(8) Uani 1 1 d .
H18 H 0.2798 -0.2549 0.0064 0.025 Uiso 1 1 calc R
C19 C 0.2459(4) -0.2045(2) -0.07219(16) 0.0211(8) Uani 1 1 d .
C22 C 0.1897(4) -0.2792(2) -0.09921(18) 0.0302(9) Uani 1 1 d .
F1 F 0.1771(5) -0.27517(19) -0.15415(12) 0.0877(15) Uani 1 1 d .
F2 F 0.0818(4) -0.3029(2) -0.07508(19) 0.0988(16) Uani 1 1 d .
F3 F 0.2671(4) -0.34351(18) -0.0905(2) 0.0962(16) Uani 1 1 d .
C20 C 0.2520(4) -0.1333(2) -0.10351(17) 0.0299(9) Uani 1 1 d .
H20 H 0.2184 -0.1312 -0.1418 0.036 Uiso 1 1 calc R
C21 C 0.3069(4) -0.0662(2) -0.07885(15) 0.0265(9) Uani 1 1 d .
H21 H 0.3139 -0.0180 -0.1008 0.032 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 0.0000 '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'
F F 0.0171 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
_geom_angle_site_symmetry_3
C3 C1 C1 137.2(3) . 2_655
C3 C1 C2 127.9(3) . .
C1 C1 C2 91.27(18) 2_655 .
C1 C3 C4 128.8(3) . .
C1 C3 C15 125.1(3) . .
C4 C3 C15 105.7(3) . .
C5 C4 C9 119.8(3) . .
C5 C4 C3 131.3(3) . .
C9 C4 C3 108.8(3) . .
C6 C5 C4 119.0(3) . .
C6 C5 H5 120.5 . .
C4 C5 H5 120.5 . .
C5 C6 C7 121.1(4) . .
C5 C6 H6 119.5 . .
C7 C6 H6 119.5 . .
C6 C7 C8 120.3(3) . .
C6 C7 H7 119.9 . .
C8 C7 H7 119.9 . .
C7 C8 C9 119.1(4) . .
C7 C8 H8 120.5 . .
C9 C8 H8 120.5 . .
C8 C9 C4 120.8(4) . .
C8 C9 C10 130.1(3) . .
C4 C9 C10 109.1(3) . .
C11 C10 C15 121.1(3) . .
C11 C10 C9 131.1(3) . .
C15 C10 C9 107.7(3) . .
C12 C11 C10 118.6(3) . .
C12 C11 H11 120.7 . .
C10 C11 H11 120.7 . .
C11 C12 C13 120.9(4) . .
C11 C12 H12 119.5 . .
C13 C12 H12 119.5 . .
C14 C13 C12 120.5(4) . .
C14 C13 H13 119.8 . .
C12 C13 H13 119.8 . .
C15 C14 C13 119.4(3) . .
C15 C14 H14 120.3 . .
C13 C14 H14 120.3 . .
C14 C15 C10 119.6(3) . .
C14 C15 C3 131.8(3) . .
C10 C15 C3 108.6(3) . .
C16 C2 C1 119.1(3) . .
C16 C2 C2 112.0(3) . 2_655
C1 C2 C2 86.65(18) . 2_655
C16 C2 H2 112.2 . .
C1 C2 H2 112.2 . .
C2 C2 H2 112.2 2_655 .
C17 C16 C21 118.5(3) . .
C17 C16 C2 122.4(3) . .
C21 C16 C2 118.9(3) . .
C18 C17 C16 121.1(3) . .
C18 C17 H17 119.4 . .
C16 C17 H17 119.4 . .
C19 C18 C17 119.2(3) . .
C19 C18 H18 120.4 . .
C17 C18 H18 120.4 . .
C18 C19 C20 120.4(3) . .
C18 C19 C22 119.4(3) . .
C20 C19 C22 120.2(3) . .
F1 C22 F2 111.1(4) . .
F1 C22 F3 104.4(4) . .
F2 C22 F3 100.9(4) . .
F1 C22 C19 114.1(3) . .
F2 C22 C19 113.2(3) . .
F3 C22 C19 111.9(4) . .
C21 C20 C19 119.5(3) . .
C21 C20 H20 120.2 . .
C19 C20 H20 120.2 . .
C20 C21 C16 121.0(3) . .
C20 C21 H21 119.5 . .
C16 C21 H21 119.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C3 1.349(5) .
C1 C1 1.458(7) 2_655
C1 C2 1.528(4) .
C3 C4 1.472(5) .
C3 C15 1.482(5) .
C4 C5 1.400(5) .
C4 C9 1.405(5) .
C5 C6 1.392(5) .
C5 H5 0.9500 .
C6 C7 1.393(5) .
C6 H6 0.9500 .
C7 C8 1.393(6) .
C7 H7 0.9500 .
C8 C9 1.394(5) .
C8 H8 0.9500 .
C9 C10 1.460(5) .
C10 C11 1.387(5) .
C10 C15 1.423(5) .
C11 C12 1.380(6) .
C11 H11 0.9500 .
C12 C13 1.402(5) .
C12 H12 0.9500 .
C13 C14 1.396(5) .
C13 H13 0.9500 .
C14 C15 1.377(5) .
C14 H14 0.9500 .
C2 C16 1.508(5) .
C2 C2 1.584(7) 2_655
C2 H2 1.0000 .
C16 C17 1.384(5) .
C16 C21 1.388(5) .
C17 C18 1.379(5) .
C17 H17 0.9500 .
C18 C19 1.379(5) .
C18 H18 0.9500 .
C19 C20 1.386(5) .
C19 C22 1.501(5) .
C22 F1 1.279(5) .
C22 F2 1.291(5) .
C22 F3 1.340(5) .
C20 C21 1.370(5) .
C20 H20 0.9500 .
C21 H21 0.9500 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C1 C1 C3 C4 -0.4(6) 2_655 .
C2 C1 C3 C4 -152.2(3) . .
C1 C1 C3 C15 171.1(4) 2_655 .
C2 C1 C3 C15 19.3(5) . .
C1 C3 C4 C5 -6.9(6) . .
C15 C3 C4 C5 -179.6(3) . .
C1 C3 C4 C9 170.7(3) . .
C15 C3 C4 C9 -2.0(4) . .
C9 C4 C5 C6 1.9(5) . .
C3 C4 C5 C6 179.3(3) . .
C4 C5 C6 C7 -0.8(5) . .
C5 C6 C7 C8 -0.9(5) . .
C6 C7 C8 C9 1.3(6) . .
C7 C8 C9 C4 -0.1(5) . .
C7 C8 C9 C10 179.3(4) . .
C5 C4 C9 C8 -1.5(5) . .
C3 C4 C9 C8 -179.5(3) . .
C5 C4 C9 C10 178.9(3) . .
C3 C4 C9 C10 1.0(4) . .
C8 C9 C10 C11 -2.2(7) . .
C4 C9 C10 C11 177.3(4) . .
C8 C9 C10 C15 -179.0(4) . .
C4 C9 C10 C15 0.5(4) . .
C15 C10 C11 C12 -0.2(5) . .
C9 C10 C11 C12 -176.6(4) . .
C10 C11 C12 C13 1.1(6) . .
C11 C12 C13 C14 -0.6(6) . .
C12 C13 C14 C15 -0.7(5) . .
C13 C14 C15 C10 1.6(5) . .
C13 C14 C15 C3 178.8(3) . .
C11 C10 C15 C14 -1.2(5) . .
C9 C10 C15 C14 176.0(3) . .
C11 C10 C15 C3 -179.0(3) . .
C9 C10 C15 C3 -1.8(4) . .
C1 C3 C15 C14 11.8(6) . .
C4 C3 C15 C14 -175.1(3) . .
C1 C3 C15 C10 -170.8(3) . .
C4 C3 C15 C10 2.3(3) . .
C3 C1 C2 C16 -100.7(4) . .
C1 C1 C2 C16 98.0(3) 2_655 .
C3 C1 C2 C2 145.9(3) . 2_655
C1 C1 C2 C2 -15.4(3) 2_655 2_655
C1 C2 C16 C17 -24.7(5) . .
C2 C2 C16 C17 74.1(3) 2_655 .
C1 C2 C16 C21 160.5(3) . .
C2 C2 C16 C21 -100.7(3) 2_655 .
C21 C16 C17 C18 1.4(5) . .
C2 C16 C17 C18 -173.4(3) . .
C16 C17 C18 C19 0.0(5) . .
C17 C18 C19 C20 -2.7(5) . .
C17 C18 C19 C22 179.3(3) . .
C18 C19 C22 F1 -167.7(4) . .
C20 C19 C22 F1 14.3(6) . .
C18 C19 C22 F2 63.9(5) . .
C20 C19 C22 F2 -114.2(5) . .
C18 C19 C22 F3 -49.4(5) . .
C20 C19 C22 F3 132.6(4) . .
C18 C19 C20 C21 3.8(6) . .
C22 C19 C20 C21 -178.2(4) . .
C19 C20 C21 C16 -2.3(6) . .
C17 C16 C21 C20 -0.3(6) . .
C2 C16 C21 C20 174.7(4) . .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.267 226 50 'C6 H14'
2 0.000 0.000 0.767 226 50 'C6 H14'
3 0.500 0.500 0.766 222 49 'C6 H14'
4 0.500 0.500 0.266 222 50 'C6 H14'
