#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:04:54 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178419 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/40/4024047.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_4024047
loop_
_publ_author_name
'John F. Tannaci'
'Masahiro Noji'
'Jennifer McBee'
'T. Don Tilley'
_publ_section_title
;
 9,10-Dichlorooctafluoroanthracene as a Building Block for
 n-Type Organic Semiconductors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5567
_journal_page_last               5573
_journal_paper_doi               10.1021/jo070404a
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C26 H10 F8'
_chemical_formula_sum            'C26 H10 F8'
_chemical_formula_weight         474.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   12.610(3)
_cell_length_b                   6.7441(19)
_cell_length_c                   22.242(6)
_cell_measurement_reflns_used    1126
_cell_measurement_temperature    168(2)
_cell_measurement_theta_max      21.41
_cell_measurement_theta_min      3.55
_cell_volume                     1891.5(9)
_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      168(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0788
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6873
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         3.55
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  .980
_exptl_absorpt_correction_T_min  .963
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'Sadabs, 2004'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          .25
_exptl_crystal_size_mid          .21
_exptl_crystal_size_min          .15
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1357
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0428
_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)+(0.0267P)²+0.7610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1145
_reflns_number_gt                953
_reflns_number_total             1357
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070404asi20070227_031224.cif
_cod_data_source_block           F8DPA
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4024047
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.86073(13) 0.0644(3) 0.64776(7) 0.0497(5) Uani 1 1 d . . .
F2 F 0.66008(13) 0.0336(3) 0.61617(7) 0.0513(5) Uani 1 1 d . . .
F3 F 1.39654(12) 0.0348(2) 0.49777(7) 0.0453(5) Uani 1 1 d . . .
F4 F 1.25498(12) 0.0793(2) 0.58300(7) 0.0454(5) Uani 1 1 d . . .
C5 C 1.0304(2) 0.0381(4) 0.56108(11) 0.0317(7) Uani 1 1 d . . .
C6 C 1.2192(2) 0.0401(4) 0.52810(11) 0.0314(7) Uani 1 1 d . . .
C7 C 0.8398(2) 0.0323(4) 0.58962(12) 0.0342(7) Uani 1 1 d . . .
C8 C 1.0635(2) 0.0825(4) 0.62394(11) 0.0346(7) Uani 1 1 d . . .
C9 C 0.9224(2) 0.0158(4) 0.54585(12) 0.0319(7) Uani 1 1 d . . .
C10 C 1.1079(2) 0.0215(4) 0.51552(12) 0.0314(7) Uani 1 1 d . . .
C11 C 0.7366(2) 0.0169(4) 0.57443(12) 0.0384(7) Uani 1 1 d . . .
C12 C 1.2933(2) 0.0200(4) 0.48490(12) 0.0345(7) Uani 1 1 d . . .
C13 C 1.0871(2) -0.0694(4) 0.66391(12) 0.0431(8) Uani 1 1 d . . .
H13A H 1.0816 -0.2008 0.6516 0.052 Uiso 1 1 calc R . .
C14 C 1.0723(2) 0.2767(4) 0.64327(11) 0.0377(7) Uani 1 1 d . . .
H14A H 1.0557 0.3797 0.6171 0.045 Uiso 1 1 calc R . .
C15 C 1.1052(2) 0.3193(5) 0.70063(13) 0.0483(8) Uani 1 1 d . . .
H15A H 1.1115 0.4505 0.7130 0.058 Uiso 1 1 calc R . .
C16 C 1.1189(2) -0.0259(5) 0.72198(14) 0.0499(8) Uani 1 1 d . . .
H16A H 1.1335 -0.1279 0.7489 0.060 Uiso 1 1 calc R . .
C17 C 1.1287(2) 0.1679(5) 0.73981(13) 0.0524(9) Uani 1 1 d . . .
H17A H 1.1514 0.1970 0.7786 0.063 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'
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C5 C10 119.1(2) . . ?
C9 C5 C8 121.2(2) . . ?
C10 C5 C8 119.7(2) . . ?
F4 C6 C12 116.1(2) . . ?
F4 C6 C10 121.9(2) . . ?
C12 C6 C10 122.0(2) . . ?
F1 C7 C11 116.5(2) . . ?
F1 C7 C9 121.8(3) . . ?
C11 C7 C9 121.8(3) . . ?
C14 C8 C13 118.9(3) . . ?
C14 C8 C5 120.3(2) . . ?
C13 C8 C5 120.8(2) . . ?
C5 C9 C7 122.1(3) . . ?
C5 C9 C10 120.2(2) . 5_756 ?
C7 C9 C10 117.7(3) . 5_756 ?
C5 C10 C6 122.0(2) . . ?
C5 C10 C9 120.7(2) . 5_756 ?
C6 C10 C9 117.4(2) . 5_756 ?
F2 C11 C7 120.9(3) . . ?
F2 C11 C12 118.3(3) . 5_756 ?
C7 C11 C12 120.8(2) . 5_756 ?
F3 C12 C6 121.0(2) . . ?
F3 C12 C11 118.7(2) . 5_756 ?
C6 C12 C11 120.3(3) . 5_756 ?
C16 C13 C8 120.2(3) . . ?
C16 C13 H13A 119.9 . . ?
C8 C13 H13A 119.9 . . ?
C15 C14 C8 120.8(3) . . ?
C15 C14 H14A 119.6 . . ?
C8 C14 H14A 119.6 . . ?
C14 C15 C17 119.9(3) . . ?
C14 C15 H15A 120.0 . . ?
C17 C15 H15A 120.0 . . ?
C17 C16 C13 119.9(3) . . ?
C17 C16 H16A 120.1 . . ?
C13 C16 H16A 120.1 . . ?
C16 C17 C15 120.3(3) . . ?
C16 C17 H17A 119.8 . . ?
C15 C17 H17A 119.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C7 1.338(3) . ?
F2 C11 1.344(3) . ?
F3 C12 1.336(3) . ?
F4 C6 1.328(3) . ?
C5 C9 1.411(4) . ?
C5 C10 1.412(4) . ?
C5 C8 1.490(4) . ?
C6 C12 1.347(4) . ?
C6 C10 1.436(4) . ?
C7 C11 1.347(4) . ?
C7 C9 1.431(4) . ?
C8 C14 1.383(4) . ?
C8 C13 1.389(4) . ?
C9 C10 1.440(4) 5_756 ?
C10 C9 1.440(4) 5_756 ?
C11 C12 1.395(4) 5_756 ?
C12 C11 1.395(4) 5_756 ?
C13 C16 1.384(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.372(4) . ?
C14 H14A 0.9300 . ?
C15 C17 1.375(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.371(5) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C5 C8 C14 -89.3(3) . . . . ?
C10 C5 C8 C14 89.5(3) . . . . ?
C9 C5 C8 C13 91.3(3) . . . . ?
C10 C5 C8 C13 -89.9(3) . . . . ?
C10 C5 C9 C7 -179.5(2) . . . . ?
C8 C5 C9 C7 -0.7(4) . . . . ?
C10 C5 C9 C10 -0.5(4) . . . 5_756 ?
C8 C5 C9 C10 178.2(2) . . . 5_756 ?
F1 C7 C9 C5 -1.8(4) . . . . ?
C11 C7 C9 C5 177.9(3) . . . . ?
F1 C7 C9 C10 179.2(2) . . . 5_756 ?
C11 C7 C9 C10 -1.1(4) . . . 5_756 ?
C9 C5 C10 C6 -179.2(2) . . . . ?
C8 C5 C10 C6 2.0(4) . . . . ?
C9 C5 C10 C9 0.5(4) . . . 5_756 ?
C8 C5 C10 C9 -178.3(2) . . . 5_756 ?
F4 C6 C10 C5 -1.9(4) . . . . ?
C12 C6 C10 C5 178.5(2) . . . . ?
F4 C6 C10 C9 178.4(2) . . . 5_756 ?
C12 C6 C10 C9 -1.2(4) . . . 5_756 ?
F1 C7 C11 F2 0.1(4) . . . . ?
C9 C7 C11 F2 -179.7(2) . . . . ?
F1 C7 C11 C12 -178.9(2) . . . 5_756 ?
C9 C7 C11 C12 1.3(4) . . . 5_756 ?
F4 C6 C12 F3 1.5(4) . . . . ?
C10 C6 C12 F3 -178.9(2) . . . . ?
F4 C6 C12 C11 -178.6(2) . . . 5_756 ?
C10 C6 C12 C11 1.0(4) . . . 5_756 ?
C14 C8 C13 C16 -0.1(4) . . . . ?
C5 C8 C13 C16 179.3(3) . . . . ?
C13 C8 C14 C15 0.9(4) . . . . ?
C5 C8 C14 C15 -178.5(2) . . . . ?
C8 C14 C15 C17 -0.7(4) . . . . ?
C8 C13 C16 C17 -1.0(4) . . . . ?
C13 C16 C17 C15 1.3(4) . . . . ?
C14 C15 C17 C16 -0.4(4) . . . . ?
