#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/42/7104297.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_7104297
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 H7 F5 O2 S3'
_chemical_formula_weight         494.46
_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                 107.7950(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2481(3)
_cell_length_b                   40.288(2)
_cell_length_c                   7.7740(4)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      1.00
_cell_volume                     1863.27(16)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'NONIUS COLLECT'
_computing_data_reduction        DENZO-SMN
_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      200(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'NONIUS KappaCCD'
_diffrn_measurement_method       'ω 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  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9650
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.01
_exptl_absorpt_coefficient_mu    0.467
_exptl_absorpt_correction_T_max  0.9548
_exptl_absorpt_correction_T_min  0.7669
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0400
_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)+(0.0495P)²+1.1641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                3332
_reflns_number_total             4183
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b820621j.txt
_cod_data_source_block           ic13240
_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 

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      P2(1)/c
_cod_database_code               7104297
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.95667(9) 0.259183(13) 0.08846(9) 0.03622(16) Uani 1 1 d . . .
S2 S 0.38417(9) 0.212055(13) 0.13712(10) 0.04084(17) Uani 1 1 d . . .
S3 S 0.94678(8) 0.162981(13) 0.08108(8) 0.03228(14) Uani 1 1 d . . .
O1 O 1.0630(3) 0.32570(4) 0.1190(3) 0.0579(6) Uani 1 1 d . . .
O2 O 1.0179(2) 0.09252(4) 0.0960(2) 0.0377(4) Uani 1 1 d . . .
C1 C 0.7730(3) 0.28991(5) 0.1126(3) 0.0330(5) Uani 1 1 d . . .
C2 C 0.5777(3) 0.27724(5) 0.1320(3) 0.0340(5) Uani 1 1 d . . .
H2 H 0.4593 0.2903 0.1490 0.041 Uiso 1 1 calc R . .
C3 C 0.5758(3) 0.24239(5) 0.1235(3) 0.0319(5) Uani 1 1 d . . .
C4 C 0.7711(3) 0.22889(5) 0.1011(3) 0.0301(4) Uani 1 1 d . . .
C5 C 0.7671(3) 0.19395(5) 0.0982(3) 0.0285(4) Uani 1 1 d . . .
C6 C 0.5675(3) 0.18118(5) 0.1146(3) 0.0312(4) Uani 1 1 d . . .
C7 C 0.5592(3) 0.14638(5) 0.1155(3) 0.0309(4) Uani 1 1 d . . .
H7 H 0.4358 0.1337 0.1266 0.037 Uiso 1 1 calc R . .
C8 C 0.7547(3) 0.13311(5) 0.0982(3) 0.0280(4) Uani 1 1 d . . .
C9 C 0.8632(4) 0.32340(5) 0.1095(3) 0.0366(5) Uani 1 1 d . . .
C10 C 0.7259(3) 0.35393(5) 0.0947(3) 0.0310(4) Uani 1 1 d . . .
C11 C 0.8401(4) 0.38358(5) 0.1491(3) 0.0354(5) Uani 1 1 d . . .
H11 H 0.9989 0.3835 0.2010 0.042 Uiso 1 1 calc R . .
C12 C 0.7243(4) 0.41313(6) 0.1281(3) 0.0397(5) Uani 1 1 d . . .
H12 H 0.8031 0.4333 0.1665 0.048 Uiso 1 1 calc R . .
C13 C 0.4919(4) 0.41349(6) 0.0506(3) 0.0403(5) Uani 1 1 d . . .
H13 H 0.4124 0.4339 0.0345 0.048 Uiso 1 1 calc R . .
C14 C 0.3773(4) 0.38419(6) -0.0025(3) 0.0375(5) Uani 1 1 d . . .
H14 H 0.2186 0.3845 -0.0549 0.045 Uiso 1 1 calc R . .
C15 C 0.4921(3) 0.35439(5) 0.0199(3) 0.0331(5) Uani 1 1 d . . .
H15 H 0.4121 0.3342 -0.0155 0.040 Uiso 1 1 calc R . .
C16 C 0.8298(3) 0.09900(5) 0.1036(3) 0.0282(4) Uani 1 1 d . . .
C17 C 0.6812(3) 0.07127(5) 0.1282(3) 0.0285(4) Uani 1 1 d . . .
C18 C 0.7701(3) 0.04760(5) 0.2607(3) 0.0347(5) Uani 1 1 d . . .
C19 C 0.6480(4) 0.02117(6) 0.2874(4) 0.0429(6) Uani 1 1 d . . .
C20 C 0.4303(4) 0.01693(6) 0.1761(4) 0.0432(6) Uani 1 1 d . . .
C21 C 0.3379(3) 0.03918(6) 0.0420(3) 0.0383(5) Uani 1 1 d . . .
C22 C 0.4606(3) 0.06633(5) 0.0209(3) 0.0310(4) Uani 1 1 d . . .
F1 F 0.9815(2) 0.05095(4) 0.3710(2) 0.0483(4) Uani 1 1 d . . .
F2 F 0.7364(3) -0.00074(4) 0.4187(3) 0.0680(5) Uani 1 1 d . . .
F3 F 0.3132(3) -0.00950(4) 0.1984(3) 0.0641(5) Uani 1 1 d . . .
F4 F 0.1313(2) 0.03391(4) -0.0713(2) 0.0526(4) Uani 1 1 d . . .
F5 F 0.3651(2) 0.08740(4) -0.11285(18) 0.0418(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
C4 S1 C1 91.18(10) . . ?
C6 S2 C3 90.55(10) . . ?
C5 S3 C8 90.81(9) . . ?
C2 C1 C9 134.7(2) . . ?
C2 C1 S1 112.68(16) . . ?
C9 C1 S1 112.62(15) . . ?
C1 C2 C3 111.18(18) . . ?
C4 C3 C2 113.59(18) . . ?
C4 C3 S2 112.27(16) . . ?
C2 C3 S2 134.13(16) . . ?
C3 C4 C5 112.34(18) . . ?
C3 C4 S1 111.35(16) . . ?
C5 C4 S1 136.29(15) . . ?
C6 C5 C4 112.36(18) . . ?
C6 C5 S3 111.45(16) . . ?
C4 C5 S3 136.19(15) . . ?
C5 C6 C7 113.95(18) . . ?
C5 C6 S2 112.47(16) . . ?
C7 C6 S2 133.54(16) . . ?
C8 C7 C6 110.60(18) . . ?
C7 C8 C16 130.87(19) . . ?
C7 C8 S3 113.19(16) . . ?
C16 C8 S3 115.81(14) . . ?
O1 C9 C1 117.2(2) . . ?
O1 C9 C10 119.6(2) . . ?
C1 C9 C10 123.27(18) . . ?
C11 C10 C15 119.3(2) . . ?
C11 C10 C9 117.27(19) . . ?
C15 C10 C9 123.33(19) . . ?
C12 C11 C10 120.3(2) . . ?
C11 C12 C13 120.1(2) . . ?
C14 C13 C12 119.9(2) . . ?
C13 C14 C15 120.3(2) . . ?
C14 C15 C10 120.0(2) . . ?
O2 C16 C8 120.58(19) . . ?
O2 C16 C17 119.19(18) . . ?
C8 C16 C17 120.15(17) . . ?
C18 C17 C22 116.44(19) . . ?
C18 C17 C16 118.86(17) . . ?
C22 C17 C16 124.62(19) . . ?
F1 C18 C19 117.9(2) . . ?
F1 C18 C17 119.79(19) . . ?
C19 C18 C17 122.3(2) . . ?
F2 C19 C18 120.9(2) . . ?
F2 C19 C20 119.7(2) . . ?
C18 C19 C20 119.4(2) . . ?
F3 C20 C21 120.3(2) . . ?
F3 C20 C19 119.5(2) . . ?
C21 C20 C19 120.2(2) . . ?
F4 C21 C20 119.8(2) . . ?
F4 C21 C22 120.6(2) . . ?
C20 C21 C22 119.6(2) . . ?
F5 C22 C21 117.82(18) . . ?
F5 C22 C17 120.14(19) . . ?
C21 C22 C17 122.0(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 C4 1.707(2) . ?
S1 C1 1.737(2) . ?
S2 C6 1.736(2) . ?
S2 C3 1.737(2) . ?
S3 C5 1.710(2) . ?
S3 C8 1.733(2) . ?
O1 C9 1.232(3) . ?
O2 C16 1.223(2) . ?
C1 C2 1.373(3) . ?
C1 C9 1.465(3) . ?
C2 C3 1.405(3) . ?
C3 C4 1.395(3) . ?
C4 C5 1.408(3) . ?
C5 C6 1.390(3) . ?
C6 C7 1.403(3) . ?
C7 C8 1.377(3) . ?
C8 C16 1.449(3) . ?
C9 C10 1.484(3) . ?
C10 C11 1.390(3) . ?
C10 C15 1.398(3) . ?
C11 C12 1.377(3) . ?
C12 C13 1.392(3) . ?
C13 C14 1.377(3) . ?
C14 C15 1.382(3) . ?
C16 C17 1.502(3) . ?
C17 C18 1.389(3) . ?
C17 C22 1.390(3) . ?
C18 F1 1.343(2) . ?
C18 C19 1.363(3) . ?
C19 F2 1.334(3) . ?
C19 C20 1.382(3) . ?
C20 F3 1.332(3) . ?
C20 C21 1.362(4) . ?
C21 F4 1.339(2) . ?
C21 C22 1.374(3) . ?
C22 F5 1.334(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653114
