#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:15:30 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178463 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/84/4028463.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_4028463
loop_
_publ_author_name
'Christian Ruzié'
'Jolanta Karpinska'
'Alan R. Kennedy'
'Yves H. Geerts'
_publ_section_title
;
 Synthesis of 1,6-, 2,7-, 3,8-, and 4,9-Isomers of
 Didodecyl[1]benzothieno[3,2-b][1]benzothiophenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7741
_journal_page_last               7748
_journal_paper_doi               10.1021/jo401134c
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C14 H8 Br2 S2'
_chemical_formula_weight         400.14
_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                 103.816(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.9821(16)
_cell_length_b                   4.1296(3)
_cell_length_c                   14.4511(11)
_cell_measurement_reflns_used    2401
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      72.7908
_cell_measurement_theta_min      4.1387
_cell_volume                     1273.88(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4334
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         72.94
_diffrn_reflns_theta_min         6.67
_exptl_absorpt_coefficient_mu    10.928
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.086
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.020
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1252
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0423
_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)+(0.0748P)²+3.5808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1217
_reflns_number_gt                1174
_reflns_number_total             1252
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo401134c_si_002.cif
_cod_data_source_block           cr760
_cod_original_cell_volume        1273.88(16)
_cod_database_code               4028463
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
Br1 Br 0.325379(18) 0.02086(10) 0.58098(3) 0.0294(2) Uani 1 1 d .
S1 S 0.52009(4) -0.0819(2) 0.89764(6) 0.0236(3) Uani 1 1 d .
C3 C 0.35826(17) -0.1385(9) 0.7067(2) 0.0223(7) Uani 1 1 d .
C4 C 0.31894(17) -0.3093(10) 0.7509(3) 0.0269(8) Uani 1 1 d .
H4 H 0.2768 -0.3515 0.7183 0.032 Uiso 1 1 calc R
C1 C 0.44209(16) -0.1859(9) 0.8457(2) 0.0227(7) Uani 1 1 d .
C2 C 0.42023(18) -0.0750(9) 0.7525(3) 0.0228(7) Uani 1 1 d .
C6 C 0.40376(17) -0.3593(9) 0.8919(3) 0.0249(7) Uani 1 1 d .
H6 H 0.4195 -0.4358 0.9551 0.030 Uiso 1 1 calc R
C5 C 0.34195(19) -0.4186(10) 0.8439(3) 0.0278(8) Uani 1 1 d .
H5 H 0.3152 -0.5348 0.8748 0.033 Uiso 1 1 calc R
C7 C 0.46782(16) 0.1069(9) 0.7125(2) 0.0223(7) Uani 1 1 d .
H7 H 0.4534 0.3353 0.6986 0.027 Uiso 1 1 calc R
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
Br1 0.0224(3) 0.0369(4) 0.0264(3) 0.00380(14) 0.0010(2) 0.00346(14)
S1 0.0196(5) 0.0291(5) 0.0217(5) 0.0004(3) 0.0040(3) -0.0021(4)
C3 0.0232(17) 0.0174(17) 0.0241(17) 0.0009(13) 0.0014(13) 0.0038(14)
C4 0.0186(16) 0.030(2) 0.0337(19) -0.0055(16) 0.0087(14) 0.0008(15)
C1 0.0188(16) 0.0248(19) 0.0239(17) -0.0041(14) 0.0041(13) 0.0020(14)
C2 0.0230(18) 0.0238(17) 0.0240(18) -0.0022(14) 0.0100(15) 0.0014(15)
C6 0.0246(17) 0.0262(19) 0.0242(17) 0.0005(15) 0.0065(14) -0.0023(15)
C5 0.0229(18) 0.0281(19) 0.034(2) -0.0030(17) 0.0093(16) -0.0026(17)
C7 0.0214(18) 0.0213(17) 0.0237(17) 0.0002(14) 0.0044(14) 0.0003(14)
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'
Br Br -0.6763 1.2805 '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
C1 S1 C7 93.55(16) . 2_656
C4 C3 C2 121.7(3) . .
C4 C3 Br1 118.7(3) . .
C2 C3 Br1 119.6(3) . .
C3 C4 C5 119.1(3) . .
C3 C4 H4 120.4 . .
C5 C4 H4 120.4 . .
C6 C1 C2 121.6(3) . .
C6 C1 S1 124.3(3) . .
C2 C1 S1 114.1(3) . .
C3 C2 C1 118.0(3) . .
C3 C2 C7 127.0(3) . .
C1 C2 C7 115.0(3) . .
C5 C6 C1 118.8(3) . .
C5 C6 H6 120.6 . .
C1 C6 H6 120.6 . .
C6 C5 C4 120.7(4) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C2 C7 C7 109.2(3) . 2_656
C2 C7 S1 112.1(3) . 2_656
C7 C7 S1 107.8(3) 2_656 2_656
C2 C7 H7 109.3 . .
C7 C7 H7 109.3 2_656 .
S1 C7 H7 109.3 2_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C3 1.906(3) .
S1 C1 1.753(4) .
S1 C7 1.847(4) 2_656
C3 C4 1.384(5) .
C3 C2 1.390(5) .
C4 C5 1.392(6) .
C4 H4 0.9500 .
C1 C6 1.391(5) .
C1 C2 1.395(5) .
C2 C7 1.511(5) .
C6 C5 1.392(5) .
C6 H6 0.9500 .
C5 H5 0.9500 .
C7 C7 1.564(7) 2_656
C7 S1 1.847(4) 2_656
C7 H7 1.0000 .
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_4
C2 C3 C4 C5 0.4(6) . .
Br1 C3 C4 C5 -178.1(3) . .
C7 S1 C1 C6 176.8(3) 2_656 .
C7 S1 C1 C2 -4.1(3) 2_656 .
C4 C3 C2 C1 -0.7(6) . .
Br1 C3 C2 C1 177.9(3) . .
C4 C3 C2 C7 179.8(4) . .
Br1 C3 C2 C7 -1.7(5) . .
C6 C1 C2 C3 0.9(6) . .
S1 C1 C2 C3 -178.2(3) . .
C6 C1 C2 C7 -179.5(3) . .
S1 C1 C2 C7 1.4(4) . .
C2 C1 C6 C5 -0.9(6) . .
S1 C1 C6 C5 178.1(3) . .
C1 C6 C5 C4 0.6(6) . .
C3 C4 C5 C6 -0.4(6) . .
C3 C2 C7 C7 -177.6(3) . 2_656
C1 C2 C7 C7 2.8(4) . 2_656
C3 C2 C7 S1 -58.3(5) . 2_656
C1 C2 C7 S1 122.2(3) . 2_656
