#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/54/2235428.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2235428
loop_
_publ_author_name
'Teh, Chin Hoong'
'Mat Salleh, Muhammad'
'Mohamed Tahir, Mohamed Ibrahim'
'Daik, Rusli'
'Kassim, Mohammad B.'
_publ_section_title
;
 2,2'-[2,5-Bis(hexyloxy)-1,4-phenylene]dithiophene
;
_journal_coeditor_code           GK2496
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1976
_journal_paper_doi               10.1107/S160053681202404X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C26 H34 O2 S2'
_chemical_formula_moiety         'C26 H34 O2 S2'
_chemical_formula_sum            'C26 H34 O2 S2'
_chemical_formula_weight         442.65
_chemical_melting_point_gt       369
_chemical_melting_point_lt       367
_chemical_name_systematic
;
2,2'-[2,5-Bis(hexyloxy)-1,4-phenylene]dithiophene
;
_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                 103.982(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.2996(3)
_cell_length_b                   5.42980(10)
_cell_length_c                   17.6872(4)
_cell_measurement_reflns_used    3985
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      71
_cell_measurement_theta_min      4
_cell_volume                     1146.23(4)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Oxford Diffraction Gemini'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8010
_diffrn_reflns_theta_full        71.34
_diffrn_reflns_theta_max         71.34
_diffrn_reflns_theta_min         3.70
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.252
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2216
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0398
_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)+(0.0739P)²+0.5049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1133
_reflns_number_gt                2018
_reflns_number_total             2216
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gk2496.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235428
_cod_database_fobs_code          2235428
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.29977(3) 0.23308(7) 0.14406(2) 0.02015(17) Uani d . 1 1
O O1 0.33781(9) 0.3460(2) 0.00566(6) 0.0185(3) Uani d . 1 1
C C1 0.41842(12) 0.1767(3) 0.00089(8) 0.0151(3) Uani d . 1 1
C C2 0.44944(12) 0.0140(3) 0.06456(8) 0.0146(3) Uani d . 1 1
C C3 0.46770(12) 0.1612(3) -0.06175(8) 0.0153(3) Uani d . 1 1
H H3 0.4451 0.2703 -0.1031 0.018 Uiso calc R 1 1
C C4 0.39762(12) 0.0159(3) 0.13132(8) 0.0144(3) Uani d . 1 1
C C5 0.41723(12) -0.1539(3) 0.19221(8) 0.0163(3) Uani d . 1 1
H H5 0.4667 -0.2856 0.1962 0.020 Uiso calc R 1 1
C C6 0.35315(13) -0.1034(3) 0.24751(9) 0.0190(3) Uani d . 1 1
H H6 0.3560 -0.1990 0.2916 0.023 Uiso calc R 1 1
C C7 0.28728(13) 0.0999(3) 0.22898(9) 0.0205(3) Uani d . 1 1
H H7 0.2408 0.1595 0.2592 0.025 Uiso calc R 1 1
C C8 0.30066(12) 0.5135(3) -0.05794(8) 0.0161(3) Uani d . 1 1
H H8A 0.2722 0.4229 -0.1059 0.019 Uiso calc R 1 1
H H8B 0.3624 0.6160 -0.0643 0.019 Uiso calc R 1 1
C C9 0.20894(12) 0.6715(3) -0.03966(8) 0.0162(3) Uani d . 1 1
H H9A 0.2394 0.7674 0.0069 0.019 Uiso calc R 1 1
H H9B 0.1504 0.5663 -0.0294 0.019 Uiso calc R 1 1
C C10 0.15873(13) 0.8453(3) -0.10717(9) 0.0173(3) Uani d . 1 1
H H10A 0.2181 0.9460 -0.1184 0.021 Uiso calc R 1 1
H H10B 0.1269 0.7482 -0.1532 0.021 Uiso calc R 1 1
C C11 0.06820(13) 1.0129(3) -0.09008(9) 0.0180(3) Uani d . 1 1
H H11A 0.1007 1.1141 -0.0451 0.022 Uiso calc R 1 1
H H11B 0.0102 0.9122 -0.0770 0.022 Uiso calc R 1 1
C C12 0.01499(13) 1.1804(3) -0.15839(9) 0.0206(3) Uani d . 1 1
H H12A 0.0732 1.2796 -0.1718 0.025 Uiso calc R 1 1
H H12B -0.0182 1.0791 -0.2032 0.025 Uiso calc R 1 1
C C13 -0.07480(13) 1.3507(3) -0.14123(10) 0.0237(4) Uani d . 1 1
H H13A -0.1337 1.2538 -0.1291 0.036 Uiso calc R 1 1
H H13B -0.1050 1.4511 -0.1861 0.036 Uiso calc R 1 1
H H13C -0.0422 1.4544 -0.0977 0.036 Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C7 S1 C4 . . 92.24(7)
C1 O1 C8 . . 118.42(11)
O1 C1 C3 . . 123.50(14)
O1 C1 C2 . . 115.58(13)
C3 C1 C2 . . 120.92(14)
C3 C2 C1 3_655 . 117.07(13)
C3 C2 C4 3_655 . 119.49(13)
C1 C2 C4 . . 123.42(13)
C1 C3 C2 . 3_655 122.00(14)
C1 C3 H3 . . 119.0
C2 C3 H3 3_655 . 119.0
C5 C4 C2 . . 126.00(13)
C5 C4 S1 . . 110.17(11)
C2 C4 S1 . . 123.82(11)
C4 C5 C6 . . 112.47(14)
C4 C5 H5 . . 123.8
C6 C5 H5 . . 123.8
C7 C6 C5 . . 112.76(14)
C7 C6 H6 . . 123.6
C5 C6 H6 . . 123.6
C6 C7 S1 . . 112.35(12)
C6 C7 H7 . . 123.8
S1 C7 H7 . . 123.8
O1 C8 C9 . . 107.75(11)
O1 C8 H8A . . 110.2
C9 C8 H8A . . 110.2
O1 C8 H8B . . 110.2
C9 C8 H8B . . 110.2
H8A C8 H8B . . 108.5
C8 C9 C10 . . 111.36(12)
C8 C9 H9A . . 109.4
C10 C9 H9A . . 109.4
C8 C9 H9B . . 109.4
C10 C9 H9B . . 109.4
H9A C9 H9B . . 108.0
C11 C10 C9 . . 112.96(12)
C11 C10 H10A . . 109.0
C9 C10 H10A . . 109.0
C11 C10 H10B . . 109.0
C9 C10 H10B . . 109.0
H10A C10 H10B . . 107.8
C10 C11 C12 . . 113.12(13)
C10 C11 H11A . . 109.0
C12 C11 H11A . . 109.0
C10 C11 H11B . . 109.0
C12 C11 H11B . . 109.0
H11A C11 H11B . . 107.8
C13 C12 C11 . . 113.32(13)
C13 C12 H12A . . 108.9
C11 C12 H12A . . 108.9
C13 C12 H12B . . 108.9
C11 C12 H12B . . 108.9
H12A C12 H12B . . 107.7
C12 C13 H13A . . 109.5
C12 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
C12 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C7 . 1.7071(15)
S1 C4 . 1.7380(15)
O1 C1 . 1.3697(18)
O1 C8 . 1.4326(17)
C1 C3 . 1.388(2)
C1 C2 . 1.409(2)
C2 C3 3_655 1.404(2)
C2 C4 . 1.471(2)
C3 C2 3_655 1.404(2)
C3 H3 . 0.9300
C4 C5 . 1.394(2)
C5 C6 . 1.423(2)
C5 H5 . 0.9300
C6 C7 . 1.362(2)
C6 H6 . 0.9300
C7 H7 . 0.9300
C8 C9 . 1.513(2)
C8 H8A . 0.9700
C8 H8B . 0.9700
C9 C10 . 1.530(2)
C9 H9A . 0.9700
C9 H9B . 0.9700
C10 C11 . 1.524(2)
C10 H10A . 0.9700
C10 H10B . 0.9700
C11 C12 . 1.527(2)
C11 H11A . 0.9700
C11 H11B . 0.9700
C12 C13 . 1.526(2)
C12 H12A . 0.9700
C12 H12B . 0.9700
C13 H13A . 0.9600
C13 H13B . 0.9600
C13 H13C . 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C5 H5 Cg1 2_645 0.93 2.85 3.5809(16) 137
