#------------------------------------------------------------------------------
#$Date: 2019-11-23 21:03:24 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234986 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/66/4036627.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_4036627
loop_
_publ_author_name
'Chen, Yung-Lung'
'Hsu, Jhih-Yang'
'Lin, Fang-Yu'
'Lai, Yu-Ying'
'Chou, Hsiao-Chieh'
'Cheng, Yen-Ju'
_publ_section_title
;
 Synthesis and Isomeric Effects of Ladder-Type Alkylated
 Terbenzodithiophene Derivatives.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2534
_journal_page_last               2542
_journal_paper_doi               10.1021/acs.joc.6b00101
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C42 H50 S4'
_chemical_formula_weight         683.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 106.940(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   37.458(2)
_cell_length_b                   5.4399(3)
_cell_length_c                   17.8501(7)
_cell_measurement_reflns_used    3403
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.6314
_cell_measurement_theta_min      2.4662
_cell_volume                     3479.5(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12013
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.633
_diffrn_reflns_theta_min         2.466
_exptl_absorpt_coefficient_mu    2.723
_exptl_absorpt_correction_T_max  0.9492
_exptl_absorpt_correction_T_min  0.6812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            'Pale Yellow'
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lamellar
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.119
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0814
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1641P)²+0.6175P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2153
_refine_ls_wR_factor_ref         0.2360
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2237
_reflns_number_total             3084
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b00101_si_002.cif
_cod_data_source_block           cu_150428lt_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

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

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        3479.4(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4036627
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.25655(3) 1.0455(2) 0.85576(6) 0.0468(4) Uani 1 1 d . .
S2 S 0.35340(4) 0.7013(2) 0.71176(6) 0.0525(4) Uani 1 1 d . .
C1 C 0.57182(16) -1.1663(10) 1.1777(3) 0.0589(12) Uani 1 1 d . .
H1 H 0.5609 -1.2695 1.1317 0.088 Uiso 1 1 calc R U
H2 H 0.5825 -1.2711 1.2234 0.088 Uiso 1 1 calc R U
H22 H 0.5915 -1.0632 1.1681 0.088 Uiso 1 1 calc R U
C2 C 0.54163(16) -1.0032(10) 1.1930(3) 0.0578(12) Uani 1 1 d . .
H21 H 0.5530 -0.8997 1.2395 0.069 Uiso 1 1 calc R U
H20 H 0.5227 -1.1091 1.2056 0.069 Uiso 1 1 calc R U
C3 C 0.52219(14) -0.8366(9) 1.1247(3) 0.0520(11) Uani 1 1 d . .
H19 H 0.5410 -0.7282 1.1125 0.062 Uiso 1 1 calc R U
H3 H 0.5109 -0.9392 1.0780 0.062 Uiso 1 1 calc R U
C4 C 0.49201(15) -0.6790(9) 1.1414(3) 0.0535(11) Uani 1 1 d . .
H4 H 0.5035 -0.5779 1.1883 0.064 Uiso 1 1 calc R U
H5 H 0.4736 -0.7889 1.1542 0.064 Uiso 1 1 calc R U
C5 C 0.47142(14) -0.5093(8) 1.0756(3) 0.0512(11) Uani 1 1 d . .
H18 H 0.4605 -0.6087 1.0279 0.061 Uiso 1 1 calc R U
H6 H 0.4896 -0.3939 1.0640 0.061 Uiso 1 1 calc R U
C6 C 0.44045(14) -0.3618(9) 1.0938(2) 0.0514(11) Uani 1 1 d . .
H7 H 0.4217 -0.4766 1.1034 0.062 Uiso 1 1 calc R U
H17 H 0.4511 -0.2661 1.1424 0.062 Uiso 1 1 calc R U
C7 C 0.42114(13) -0.1868(8) 1.0281(2) 0.0492(10) Uani 1 1 d . .
H24 H 0.4111 -0.2843 0.9796 0.059 Uiso 1 1 calc R U
H23 H 0.4402 -0.0736 1.0190 0.059 Uiso 1 1 calc R U
C8 C 0.38948(13) -0.0330(8) 1.0409(2) 0.0485(10) Uani 1 1 d . .
H16 H 0.3985 0.0603 1.0904 0.058 Uiso 1 1 calc R U
H8 H 0.3690 -0.1422 1.0450 0.058 Uiso 1 1 calc R U
C9 C 0.37497(13) 0.1447(8) 0.9728(2) 0.0478(10) Uani 1 1 d . .
H9 H 0.3958 0.2523 0.9696 0.057 Uiso 1 1 calc R U
H10 H 0.3670 0.0486 0.9236 0.057 Uiso 1 1 calc R U
C10 C 0.34254(13) 0.3064(8) 0.9777(2) 0.0461(10) Uani 1 1 d . .
H15 H 0.3501 0.3974 1.0279 0.055 Uiso 1 1 calc R U
H25 H 0.3212 0.1994 0.9782 0.055 Uiso 1 1 calc R U
C11 C 0.32944(13) 0.4918(8) 0.9107(2) 0.0470(10) Uani 1 1 d . .
C12 C 0.30078(13) 0.6634(8) 0.9088(2) 0.0474(10) Uani 1 1 d . .
C13 C 0.27696(13) 0.6892(8) 0.9607(2) 0.0456(10) Uani 1 1 d . .
C14 C 0.25164(13) 0.8897(8) 0.9379(2) 0.0452(10) Uani 1 1 d . .
C15 C 0.27474(13) 0.5483(8) 1.0241(2) 0.0454(10) Uani 1 1 d . .
H11 H 0.2909 0.4120 1.0412 0.055 Uiso 1 1 calc R U
C16 C 0.29171(13) 0.8437(8) 0.8499(2) 0.0468(10) Uani 1 1 d . .
C17 C 0.30937(13) 0.8543(8) 0.7900(2) 0.0470(10) Uani 1 1 d . .
C18 C 0.30403(14) 1.0204(9) 0.7253(2) 0.0492(10) Uani 1 1 d . .
H14 H 0.2874 1.1566 0.7158 0.059 Uiso 1 1 calc R U
C19 C 0.32570(15) 0.9578(9) 0.6795(2) 0.0522(11) Uani 1 1 d . .
H13 H 0.3257 1.0466 0.6337 0.063 Uiso 1 1 calc R U
C20 C 0.33583(14) 0.6728(8) 0.7915(3) 0.0491(10) Uani 1 1 d . .
C21 C 0.34632(13) 0.4957(8) 0.8508(2) 0.0481(10) Uani 1 1 d . .
H12 H 0.3650 0.3781 0.8502 0.058 Uiso 1 1 calc R U
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C16 S1 C14 90.6(2) . .
C19 S2 C20 90.6(2) . .
C2 C1 H1 109.5 . .
C2 C1 H2 109.5 . .
H1 C1 H2 109.5 . .
C2 C1 H22 109.5 . .
H1 C1 H22 109.5 . .
H2 C1 H22 109.5 . .
C1 C2 C3 114.2(4) . .
C1 C2 H21 108.7 . .
C3 C2 H21 108.7 . .
C1 C2 H20 108.7 . .
C3 C2 H20 108.7 . .
H21 C2 H20 107.6 . .
C4 C3 C2 112.9(4) . .
C4 C3 H19 109.0 . .
C2 C3 H19 109.0 . .
C4 C3 H3 109.0 . .
C2 C3 H3 109.0 . .
H19 C3 H3 107.8 . .
C3 C4 C5 115.6(4) . .
C3 C4 H4 108.4 . .
C5 C4 H4 108.4 . .
C3 C4 H5 108.4 . .
C5 C4 H5 108.4 . .
H4 C4 H5 107.4 . .
C4 C5 C6 113.7(4) . .
C4 C5 H18 108.8 . .
C6 C5 H18 108.8 . .
C4 C5 H6 108.8 . .
C6 C5 H6 108.8 . .
H18 C5 H6 107.7 . .
C7 C6 C5 112.7(4) . .
C7 C6 H7 109.1 . .
C5 C6 H7 109.1 . .
C7 C6 H17 109.1 . .
C5 C6 H17 109.1 . .
H7 C6 H17 107.8 . .
C6 C7 C8 116.4(4) . .
C6 C7 H24 108.2 . .
C8 C7 H24 108.2 . .
C6 C7 H23 108.2 . .
C8 C7 H23 108.2 . .
H24 C7 H23 107.3 . .
C7 C8 C9 110.0(3) . .
C7 C8 H16 109.7 . .
C9 C8 H16 109.7 . .
C7 C8 H8 109.7 . .
C9 C8 H8 109.7 . .
H16 C8 H8 108.2 . .
C10 C9 C8 115.2(4) . .
C10 C9 H9 108.5 . .
C8 C9 H9 108.5 . .
C10 C9 H10 108.5 . .
C8 C9 H10 108.5 . .
H9 C9 H10 107.5 . .
C9 C10 C11 114.5(4) . .
C9 C10 H15 108.6 . .
C11 C10 H15 108.6 . .
C9 C10 H25 108.6 . .
C11 C10 H25 108.6 . .
H15 C10 H25 107.6 . .
C21 C11 C12 118.8(4) . .
C21 C11 C10 119.7(4) . .
C12 C11 C10 121.5(4) . .
C16 C12 C11 119.7(4) . .
C16 C12 C13 110.3(4) . .
C11 C12 C13 130.0(4) . .
C15 C13 C14 117.6(4) . .
C15 C13 C12 130.8(4) . .
C14 C13 C12 111.6(4) . .
C15 C14 C13 123.6(4) 7_567 .
C15 C14 S1 123.6(3) 7_567 .
C13 C14 S1 112.7(3) . .
C13 C15 C14 118.8(4) . 7_567
C13 C15 H11 120.6 . .
C14 C15 H11 120.6 7_567 .
C12 C16 C17 122.0(4) . .
C12 C16 S1 114.7(3) . .
C17 C16 S1 123.3(3) . .
C20 C17 C16 116.4(4) . .
C20 C17 C18 113.1(4) . .
C16 C17 C18 130.5(4) . .
C19 C18 C17 111.2(4) . .
C19 C18 H14 124.4 . .
C17 C18 H14 124.4 . .
C18 C19 S2 114.1(3) . .
C18 C19 H13 123.0 . .
S2 C19 H13 123.0 . .
C17 C20 C21 122.9(4) . .
C17 C20 S2 111.0(3) . .
C21 C20 S2 126.1(4) . .
C11 C21 C20 120.1(4) . .
C11 C21 H12 120.0 . .
C20 C21 H12 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C16 1.741(5) .
S1 C14 1.749(4) .
S2 C19 1.734(5) .
S2 C20 1.741(4) .
C1 C2 1.524(7) .
C1 H1 0.9800 .
C1 H2 0.9800 .
C1 H22 0.9800 .
C2 C3 1.524(6) .
C2 H21 0.9900 .
C2 H20 0.9900 .
C3 C4 1.516(7) .
C3 H19 0.9900 .
C3 H3 0.9900 .
C4 C5 1.516(6) .
C4 H4 0.9900 .
C4 H5 0.9900 .
C5 C6 1.522(6) .
C5 H18 0.9900 .
C5 H6 0.9900 .
C6 C7 1.520(6) .
C6 H7 0.9900 .
C6 H17 0.9900 .
C7 C8 1.522(6) .
C7 H24 0.9900 .
C7 H23 0.9900 .
C8 C9 1.524(6) .
C8 H16 0.9900 .
C8 H8 0.9900 .
C9 C10 1.523(6) .
C9 H9 0.9900 .
C9 H10 0.9900 .
C10 C11 1.531(6) .
C10 H15 0.9900 .
C10 H25 0.9900 .
C11 C21 1.392(6) .
C11 C12 1.416(6) .
C12 C16 1.405(6) .
C12 C13 1.469(6) .
C13 C15 1.389(6) .
C13 C14 1.425(6) .
C14 C15 1.393(6) 7_567
C15 C14 1.393(6) 7_567
C15 H11 0.9500 .
C16 C17 1.413(6) .
C17 C20 1.393(7) .
C17 C18 1.434(6) .
C18 C19 1.353(7) .
C18 H14 0.9500 .
C19 H13 0.9500 .
C20 C21 1.400(6) .
C21 H12 0.9500 .
