#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:07:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178421 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/42/4024261.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_4024261
loop_
_publ_author_name
'Katharine Geramita'
'Jennifer McBee'
'T. Don Tilley'
_publ_section_title
;
2,7-Substituted Hexafluoroheterofluorenes as Potential Building Blocks for
Electron Transporting Materials
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              820
_journal_page_last               829
_journal_paper_doi               10.1021/jo802171t
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C14 H6 F8 Si'
_chemical_formula_sum            'C14 H6 F8 Si'
_chemical_formula_weight         354.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 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                 99.108(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4531(16)
_cell_length_b                   17.842(3)
_cell_length_c                   7.3749(11)
_cell_measurement_reflns_used    2308
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      30.81
_cell_measurement_theta_min      2.49
_cell_volume                     1358.1(4)
_computing_cell_refinement       'Saint v7.06, Bruker 2004'
_computing_data_collection       'Apex2-v1.0.27, Bruker 2004'
_computing_data_reduction        'Saint v7.06, Bruker 2004'
_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      193(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Platinum 200'
_diffrn_measurement_method       ω/2θ-scans
_diffrn_radiation_monochromator  'Si-<111> channel cut crystal'
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.77490
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6961
_diffrn_reflns_theta_full        31.10
_diffrn_reflns_theta_max         31.10
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'Sadabs, 2004'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         1682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0449
_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)+(0.0942P)²+0.3512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1551
_reflns_number_gt                1348
_reflns_number_total             1682
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802171t_si_002.cif
_cod_data_source_block           kath30
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      C2/c
_cod_database_code               4024261
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.0000 0.18841(4) 0.2500 0.0515(3) Uani 1 2 d S . .
F1 F 0.28217(13) 0.19187(8) 0.1333(2) 0.0769(4) Uani 1 1 d . . .
F2 F 0.42706(14) 0.07161(12) 0.0709(2) 0.0902(5) Uani 1 1 d . . .
F4 F 0.1114(2) -0.08996(8) 0.2167(2) 0.0915(6) Uani 1 1 d . . .
C7 C 0.06625(19) 0.04111(10) 0.2246(2) 0.0513(5) Uani 1 1 d . . .
F3 F 0.33767(19) -0.06776(10) 0.1203(2) 0.1006(6) Uani 1 1 d . . .
C5 C 0.2661(3) -0.00778(15) 0.1482(3) 0.0709(7) Uani 1 1 d . . .
C3 C 0.2360(2) 0.12264(13) 0.1547(3) 0.0594(5) Uani 1 1 d . . .
C2 C 0.11590(18) 0.11359(11) 0.2038(3) 0.0507(4) Uani 1 1 d . . .
C1 C 0.0602(2) 0.24625(13) 0.4532(4) 0.0709(6) Uani 1 1 d . . .
H10A H -0.0035 0.2834 0.4695 0.106 Uiso 1 1 calc R . .
H10B H 0.1392 0.2706 0.4356 0.106 Uiso 1 1 calc R . .
H10C H 0.0762 0.2149 0.5601 0.106 Uiso 1 1 calc R . .
C4 C 0.3125(2) 0.06226(16) 0.1245(3) 0.0671(6) Uani 1 1 d . . .
C6 C 0.1452(2) -0.01909(12) 0.1972(3) 0.0634(6) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Si1 0.0372(4) 0.0456(4) 0.0740(5) 0.000 0.0156(3) 0.000
F1 0.0493(7) 0.0832(9) 0.1037(11) 0.0008(7) 0.0291(7) -0.0055(6)
F2 0.0554(8) 0.1371(15) 0.0821(10) -0.0071(9) 0.0237(7) 0.0291(8)
F4 0.1315(16) 0.0499(7) 0.0935(11) -0.0035(6) 0.0193(10) 0.0188(8)
C7 0.0577(11) 0.0513(10) 0.0433(9) -0.0018(7) 0.0031(7) 0.0065(7)
F3 0.1140(14) 0.1000(12) 0.0894(10) -0.0129(9) 0.0216(10) 0.0598(10)
C5 0.0782(15) 0.0812(15) 0.0525(11) -0.0070(10) 0.0083(10) 0.0379(12)
C3 0.0455(10) 0.0715(12) 0.0621(11) -0.0017(9) 0.0113(8) 0.0083(9)
C2 0.0428(9) 0.0542(10) 0.0554(10) -0.0008(7) 0.0085(7) 0.0059(7)
C1 0.0558(11) 0.0583(12) 0.1000(18) -0.0183(11) 0.0167(11) -0.0035(9)
C4 0.0527(11) 0.0952(17) 0.0541(11) -0.0055(10) 0.0108(9) 0.0234(11)
C6 0.0829(15) 0.0557(11) 0.0493(10) -0.0039(8) 0.0034(10) 0.0170(10)
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'
Si Si 0.0817 0.0704 '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
C1 Si1 C1 112.03(17) . 2 ?
C1 Si1 C2 113.55(9) . . ?
C1 Si1 C2 113.49(10) 2 . ?
C1 Si1 C2 113.49(10) . 2 ?
C1 Si1 C2 113.55(9) 2 2 ?
C2 Si1 C2 88.89(13) . 2 ?
C6 C7 C2 117.1(2) . . ?
C6 C7 C7 129.33(14) . 2 ?
C2 C7 C7 113.56(11) . 2 ?
F3 C5 C4 119.6(3) . . ?
F3 C5 C6 118.6(3) . . ?
C4 C5 C6 121.74(19) . . ?
F1 C3 C2 120.01(18) . . ?
F1 C3 C4 118.1(2) . . ?
C2 C3 C4 121.9(2) . . ?
C3 C2 C7 120.33(18) . . ?
C3 C2 Si1 127.67(16) . . ?
C7 C2 Si1 111.99(14) . . ?
Si1 C1 H10A 109.5 . . ?
Si1 C1 H10B 109.5 . . ?
H10A C1 H10B 109.5 . . ?
Si1 C1 H10C 109.5 . . ?
H10A C1 H10C 109.5 . . ?
H10B C1 H10C 109.5 . . ?
F2 C4 C5 120.6(2) . . ?
F2 C4 C3 121.4(3) . . ?
C5 C4 C3 117.9(2) . . ?
F4 C6 C5 115.9(2) . . ?
F4 C6 C7 123.1(2) . . ?
C5 C6 C7 120.9(2) . . ?
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
Si1 C1 1.846(2) . ?
Si1 C1 1.846(2) 2 ?
Si1 C2 1.8699(19) . ?
Si1 C2 1.8699(19) 2 ?
F1 C3 1.344(3) . ?
F2 C4 1.330(3) . ?
F4 C6 1.327(3) . ?
C7 C6 1.389(3) . ?
C7 C2 1.411(3) . ?
C7 C7 1.491(4) 2 ?
F3 C5 1.340(2) . ?
C5 C4 1.362(4) . ?
C5 C6 1.383(4) . ?
C3 C2 1.370(3) . ?
C3 C4 1.380(3) . ?
C1 H10A 0.9600 . ?
C1 H10B 0.9600 . ?
C1 H10C 0.9600 . ?
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
F1 C3 C2 C7 179.30(17) . . . . ?
C4 C3 C2 C7 -0.2(3) . . . . ?
F1 C3 C2 Si1 -0.6(3) . . . . ?
C4 C3 C2 Si1 179.97(15) . . . . ?
C6 C7 C2 C3 1.3(3) . . . . ?
C7 C7 C2 C3 -179.08(19) 2 . . . ?
C6 C7 C2 Si1 -178.77(14) . . . . ?
C7 C7 C2 Si1 0.8(2) 2 . . . ?
C1 Si1 C2 C3 -65.2(2) . . . . ?
C1 Si1 C2 C3 64.3(2) 2 . . . ?
C2 Si1 C2 C3 179.6(2) 2 . . . ?
C1 Si1 C2 C7 114.95(15) . . . . ?
C1 Si1 C2 C7 -115.59(15) 2 . . . ?
C2 Si1 C2 C7 -0.30(9) 2 . . . ?
F3 C5 C4 F2 1.2(3) . . . . ?
C6 C5 C4 F2 -177.55(19) . . . . ?
F3 C5 C4 C3 -179.91(19) . . . . ?
C6 C5 C4 C3 1.3(3) . . . . ?
F1 C3 C4 F2 -1.8(3) . . . . ?
C2 C3 C4 F2 177.69(19) . . . . ?
F1 C3 C4 C5 179.34(19) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
F3 C5 C6 F4 1.5(3) . . . . ?
C4 C5 C6 F4 -179.71(19) . . . . ?
F3 C5 C6 C7 -178.91(18) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C2 C7 C6 F4 178.35(16) . . . . ?
C7 C7 C6 F4 -1.1(4) 2 . . . ?
C2 C7 C6 C5 -1.2(3) . . . . ?
C7 C7 C6 C5 179.3(2) 2 . . . ?
