#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/42/7104296.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_7104296
loop_
_publ_author_name
'Chen, Ming-Chou'
'Chiang, Yen-Ju'
'Kim, Choongik'
'Guo, Yue-Jhih'
'Chen, Sheng-Yu'
'Liang, You-Jhih'
'Huang, Yu-Wen'
'Hu, Tarng-Shiang'
'Lee, Gene-Hsiang'
'Facchetti, Antonio'
'Marks, Tobin J'
_publ_section_title
;
 One-pot [1+1+1] synthesis of dithieno[2,3-b:3',2'-d]thiophene (DTT)
 and their functionalized derivatives for organic thin-film
 transistors.
;
_journal_issue                   14
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1846
_journal_page_last               1848
_journal_paper_doi               10.1039/b820621j
_journal_volume                  34
_journal_year                    2009
_chemical_formula_sum            'C22 H2 F10 O2 S3'
_chemical_formula_weight         584.42
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.105(1)
_cell_angle_beta                 97.954(1)
_cell_angle_gamma                93.810(1)
_cell_formula_units_Z            2
_cell_length_a                   6.1883(3)
_cell_length_b                   9.3340(5)
_cell_length_c                   18.096(1)
_cell_measurement_reflns_used    3482
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.78
_cell_volume                     1003.04(9)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'BRUKER SMART APEXCCD area detector'
_diffrn_measurement_method       '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  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13000
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.17
_exptl_absorpt_coefficient_mu    0.485
_exptl_absorpt_correction_T_max  0.9531
_exptl_absorpt_correction_T_min  0.7279
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0413
_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)+(0.0341P)²+0.6205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0931
_reflns_number_gt                3787
_reflns_number_total             4567
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b820621j.txt
_cod_data_source_block           ic12833
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7104296
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
S1 S 0.53700(9) 0.81187(7) 1.00184(3) 0.02561(15) Uani 1 1 d . . .
S2 S 1.14139(9) 0.66702(7) 1.06927(3) 0.02197(14) Uani 1 1 d . . .
S3 S 1.07809(9) 0.82915(7) 0.88858(3) 0.02177(14) Uani 1 1 d . . .
O1 O 1.2672(3) 0.5634(2) 1.20365(10) 0.0362(4) Uani 1 1 d . . .
O2 O 1.0988(3) 0.9228(2) 0.75056(10) 0.0403(5) Uani 1 1 d . . .
C1 C 0.9387(3) 0.7413(2) 1.02014(12) 0.0186(4) Uani 1 1 d . . .
C2 C 0.7480(3) 0.7424(3) 1.05265(12) 0.0200(4) Uani 1 1 d . . .
C3 C 0.7667(4) 0.6864(3) 1.11940(12) 0.0212(5) Uani 1 1 d . . .
H3 H 0.6531 0.6806 1.1493 0.025 Uiso 1 1 calc R . .
C4 C 0.9708(4) 0.6416(3) 1.13505(12) 0.0209(5) Uani 1 1 d . . .
C5 C 1.0751(4) 0.5846(3) 1.19878(13) 0.0230(5) Uani 1 1 d . . .
C6 C 0.9483(4) 0.5603(3) 1.26062(13) 0.0218(5) Uani 1 1 d . . .
C7 C 0.7448(4) 0.4782(2) 1.24683(13) 0.0216(5) Uani 1 1 d . . .
C8 C 0.6434(4) 0.4505(3) 1.30567(14) 0.0248(5) Uani 1 1 d . . .
C9 C 0.7412(4) 0.5056(3) 1.38064(14) 0.0279(5) Uani 1 1 d . . .
C10 C 0.9419(4) 0.5890(3) 1.39695(13) 0.0288(5) Uani 1 1 d . . .
C11 C 1.0427(4) 0.6140(3) 1.33734(13) 0.0249(5) Uani 1 1 d . . .
C12 C 0.9155(3) 0.7988(2) 0.95386(12) 0.0193(4) Uani 1 1 d . . .
C13 C 0.7051(4) 0.8374(3) 0.93524(12) 0.0212(5) Uani 1 1 d . . .
C14 C 0.6714(4) 0.8859(3) 0.86656(13) 0.0230(5) Uani 1 1 d . . .
H14 H 0.5359 0.9130 0.8449 0.028 Uiso 1 1 calc R . .
C15 C 0.8610(4) 0.8888(3) 0.83540(12) 0.0210(5) Uani 1 1 d . . .
C16 C 0.9110(4) 0.9201(3) 0.76351(13) 0.0251(5) Uani 1 1 d . . .
C17 C 0.7293(4) 0.9372(3) 0.70292(12) 0.0217(5) Uani 1 1 d . . .
C18 C 0.7169(4) 0.8521(3) 0.62854(13) 0.0261(5) Uani 1 1 d . . .
C19 C 0.5521(4) 0.8588(3) 0.57055(13) 0.0295(6) Uani 1 1 d . . .
C20 C 0.3963(4) 0.9551(3) 0.58521(14) 0.0297(6) Uani 1 1 d . . .
C21 C 0.4067(4) 1.0447(3) 0.65764(14) 0.0273(5) Uani 1 1 d . . .
C22 C 0.5700(4) 1.0337(3) 0.71521(13) 0.0237(5) Uani 1 1 d . . .
F1 F 0.6459(2) 0.42007(15) 1.17454(7) 0.0270(3) Uani 1 1 d . . .
F2 F 0.4505(2) 0.36688(16) 1.29080(9) 0.0352(4) Uani 1 1 d . . .
F3 F 0.6412(3) 0.47815(18) 1.43747(8) 0.0396(4) Uani 1 1 d . . .
F4 F 1.0341(3) 0.64515(18) 1.46972(8) 0.0430(4) Uani 1 1 d . . .
F5 F 1.2365(2) 0.69673(18) 1.35495(8) 0.0388(4) Uani 1 1 d . . .
F6 F 0.8618(3) 0.75341(18) 0.61231(8) 0.0401(4) Uani 1 1 d . . .
F7 F 0.5435(3) 0.77366(18) 0.49984(8) 0.0435(4) Uani 1 1 d . . .
F8 F 0.2369(3) 0.96359(18) 0.52916(9) 0.0442(4) Uani 1 1 d . . .
F9 F 0.2600(3) 1.14236(18) 0.67139(10) 0.0430(4) Uani 1 1 d . . .
F10 F 0.5741(3) 1.12251(16) 0.78516(8) 0.0346(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'
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'
S S 0.1246 0.1234 '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
C2 S1 C13 90.41(11) . . ?
C1 S2 C4 90.54(10) . . ?
C12 S3 C15 91.08(11) . . ?
C2 C1 C12 112.15(19) . . ?
C2 C1 S2 111.90(16) . . ?
C12 C1 S2 135.94(17) . . ?
C1 C2 C3 113.43(19) . . ?
C1 C2 S1 112.67(16) . . ?
C3 C2 S1 133.90(17) . . ?
C4 C3 C2 110.77(19) . . ?
C3 C4 C5 132.1(2) . . ?
C3 C4 S2 113.34(16) . . ?
C5 C4 S2 114.49(16) . . ?
O1 C5 C4 120.1(2) . . ?
O1 C5 C6 119.7(2) . . ?
C4 C5 C6 120.16(19) . . ?
C7 C6 C11 116.4(2) . . ?
C7 C6 C5 124.2(2) . . ?
C11 C6 C5 119.2(2) . . ?
F1 C7 C8 118.3(2) . . ?
F1 C7 C6 119.9(2) . . ?
C8 C7 C6 121.7(2) . . ?
F2 C8 C7 120.6(2) . . ?
F2 C8 C9 119.2(2) . . ?
C7 C8 C9 120.2(2) . . ?
F3 C9 C8 119.8(2) . . ?
F3 C9 C10 120.3(2) . . ?
C8 C9 C10 120.0(2) . . ?
F4 C10 C11 121.0(2) . . ?
F4 C10 C9 119.9(2) . . ?
C11 C10 C9 119.1(2) . . ?
F5 C11 C10 117.8(2) . . ?
F5 C11 C6 119.7(2) . . ?
C10 C11 C6 122.5(2) . . ?
C13 C12 C1 112.40(19) . . ?
C13 C12 S3 111.11(16) . . ?
C1 C12 S3 136.46(17) . . ?
C12 C13 C14 114.1(2) . . ?
C12 C13 S1 112.30(16) . . ?
C14 C13 S1 133.64(18) . . ?
C15 C14 C13 110.7(2) . . ?
C14 C15 C16 132.7(2) . . ?
C14 C15 S3 112.99(16) . . ?
C16 C15 S3 114.12(16) . . ?
O2 C16 C15 120.0(2) . . ?
O2 C16 C17 119.6(2) . . ?
C15 C16 C17 120.3(2) . . ?
C22 C17 C18 116.3(2) . . ?
C22 C17 C16 124.8(2) . . ?
C18 C17 C16 118.9(2) . . ?
F6 C18 C19 117.7(2) . . ?
F6 C18 C17 120.0(2) . . ?
C19 C18 C17 122.2(2) . . ?
F7 C19 C20 119.7(2) . . ?
F7 C19 C18 120.6(2) . . ?
C20 C19 C18 119.7(2) . . ?
F8 C20 C19 120.2(2) . . ?
F8 C20 C21 119.9(2) . . ?
C19 C20 C21 119.9(2) . . ?
F9 C21 C22 120.5(2) . . ?
F9 C21 C20 120.0(2) . . ?
C22 C21 C20 119.4(2) . . ?
F10 C22 C21 117.7(2) . . ?
F10 C22 C17 119.9(2) . . ?
C21 C22 C17 122.4(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
S1 C2 1.738(2) . ?
S1 C13 1.742(2) . ?
S2 C1 1.712(2) . ?
S2 C4 1.741(2) . ?
S3 C12 1.712(2) . ?
S3 C15 1.739(2) . ?
O1 C5 1.213(3) . ?
O2 C16 1.217(3) . ?
C1 C2 1.389(3) . ?
C1 C12 1.415(3) . ?
C2 C3 1.415(3) . ?
C3 C4 1.369(3) . ?
C4 C5 1.465(3) . ?
C5 C6 1.501(3) . ?
C6 C7 1.391(3) . ?
C6 C11 1.393(3) . ?
C7 F1 1.339(3) . ?
C7 C8 1.372(3) . ?
C8 F2 1.341(3) . ?
C8 C9 1.373(3) . ?
C9 F3 1.334(3) . ?
C9 C10 1.379(4) . ?
C10 F4 1.332(3) . ?
C10 C11 1.374(3) . ?
C11 F5 1.340(3) . ?
C12 C13 1.391(3) . ?
C13 C14 1.411(3) . ?
C14 C15 1.372(3) . ?
C15 C16 1.465(3) . ?
C16 C17 1.501(3) . ?
C17 C22 1.385(3) . ?
C17 C18 1.388(3) . ?
C18 F6 1.341(3) . ?
C18 C19 1.374(3) . ?
C19 F7 1.336(3) . ?
C19 C20 1.373(4) . ?
C20 F8 1.333(3) . ?
C20 C21 1.377(4) . ?
C21 F9 1.337(3) . ?
C21 C22 1.374(3) . ?
C22 F10 1.343(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653113
