Sulfoxide-directed metal-free cross-couplings in the expedient synthesis of benzothiophene-based components of materials
Eberhart, Andrew J.; Shrives, Harry; Zhang, Yuntong; Carrër, Amandine; Parry, Adam V. S.; Tate, Daniel J.; Turner, Michael L.; Procter, David J.; Chem. Sci. 7 (2016) 1281–; doi:10.1039/C5SC03823E

data_1540520
_publ_section_title
;
 Sulfoxide-directed metal-free cross-couplings in the expedient synthesis
 of benzothiophene-based components of materials
;
_journal_issue                   2
_journal_name_full               'Chem. Sci.'
_journal_page_first              1281
_journal_paper_doi               10.1039/C5SC03823E
_journal_volume                  7
_journal_year                    2016
_chemical_formula_sum            'C28 H36 S2'
_chemical_formula_weight         436.69
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_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
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_audit_creation_date
;
'Thu Oct 30 12:03:12 2014'
;
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;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_audit_update_record
;
2015-07-27 deposited with the CCDC.
2015-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                67.240(5)
_cell_angle_beta                 76.721(6)
_cell_angle_gamma                79.135(6)
_cell_formula_units_Z            1
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_cell_length_c                   11.6714(6)
_cell_measurement_reflns_used    3602
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.2848
_cell_measurement_theta_min      4.1672
_cell_volume                     586.18(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_details
;
  1 omega   51.19  208.19   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   73.8669  184.2094 157

  2 phi      0.30  307.49   1.0006   11.0000
omega____ theta____ kappa____ phi______ frames
 140.9194  110.0000   73.8669     -     307

  3 omega   81.54  239.54   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   73.8669  299.2100 158

  4 phi     75.48  287.61   1.0006   11.0000
omega____ theta____ kappa____ phi______ frames
 177.3394  110.0000   73.8669     -     212

  5 omega  -64.62  113.38   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.0000   73.8669   16.7088 178

  6 phi     17.67  333.87   1.0006   11.0000
omega____ theta____ kappa____ phi______ frames
 119.2097  110.0000   73.8669     -     316

  7 omega  109.30  233.30   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   73.8669   -5.7906 124

  8 phi     56.72  279.86   1.0006    5.5000
omega____ theta____ kappa____ phi______ frames
 114.6197   85.0000   73.8669     -     223

  9 omega  177.70  261.70   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   73.8669  184.2094 84

 10 omega  195.71  268.71   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      110.0000   73.8669   34.2088 73

 11 phi    178.40  315.49   1.0006    5.5000
omega____ theta____ kappa____ phi______ frames
 204.6594   75.0000   73.8669     -     137

 12 phi     75.55  158.65   1.0012   11.0000
omega____ theta____ kappa____ phi______ frames
 228.1494  105.0000   73.8669     -     83

 13 omega   78.21  154.21   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   73.8669  271.7094 76

 14 omega  176.80  258.80   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   73.8669  229.2094 82

 15 phi    186.63  262.68   1.0006    5.5000
omega____ theta____ kappa____ phi______ frames
 151.3494   18.0000   73.8669     -     76

 16 omega  106.47  178.47   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   73.8669  174.2088 72

 17 omega  153.26  228.26   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   73.8669   79.2087 75

;
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \p scans'
_diffrn_orient_matrix_UB_11      0.0075624000
_diffrn_orient_matrix_UB_12      0.1399781000
_diffrn_orient_matrix_UB_13      -0.1278968000
_diffrn_orient_matrix_UB_21      0.1546677000
_diffrn_orient_matrix_UB_22      -0.1089732000
_diffrn_orient_matrix_UB_23      -0.0653247000
_diffrn_orient_matrix_UB_31      -0.2058212000
_diffrn_orient_matrix_UB_32      -0.0510943000
_diffrn_orient_matrix_UB_33      -0.0223056000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5523
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         74.46
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_exptl_absorpt_coefficient_mu    2.129
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.850
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2227
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0611
_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/[\s^2^(Fo^2^)+(0.1426P)^2^+0.3267P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.1693
_reflns_number_gt                2100
_reflns_number_total             2227
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5sc03823e2.cif
_cod_data_source_block           s4124oa
_cod_depositor_comments
'Adding full bibliography for 1540519--1540523.cif.'
_cod_original_cell_volume        586.18(7)
_cod_database_code               1540520