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_1540521
_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 H32 O2 S2'
_chemical_formula_weight         464.66
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-07-27 deposited with the CCDC.
2015-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                80.515(2)
_cell_angle_beta                 88.025(2)
_cell_angle_gamma                77.197(2)
_cell_formula_units_Z            2
_cell_length_a                   5.4552(2)
_cell_length_b                   9.1130(3)
_cell_length_c                   24.9685(8)
_cell_measurement_reflns_used    5254
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.28
_cell_measurement_theta_min      3.59
_cell_volume                     1193.85(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11344
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         72.27
_diffrn_reflns_theta_min         3.59
_exptl_absorpt_coefficient_mu    2.192
_exptl_absorpt_correction_T_max  0.9174
_exptl_absorpt_correction_T_min  0.79469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0360
_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/[\s^2^(Fo^2^)+(0.0677P)^2^+0.2781P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1033
_reflns_number_gt                3936
_reflns_number_total             4503
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5sc03823e2.cif
_cod_data_source_block           s4117ma
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1540519--1540523.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1540521