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_1540522
_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           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                90.00
_cell_angle_beta                 92.346(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2121(4)
_cell_length_b                   10.8647(2)
_cell_length_c                   19.8947(4)
_cell_measurement_reflns_used    1909
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      72.07
_cell_measurement_theta_min      4.45
_cell_volume                     2421.46(11)
_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      180(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.973
_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  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0653
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11529
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         72.19
_diffrn_reflns_theta_min         4.45
_exptl_absorpt_coefficient_mu    2.162
_exptl_absorpt_correction_T_max  0.9185
_exptl_absorpt_correction_T_min  0.711301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0294P)^2^+0.2936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1080
_reflns_number_gt                3492
_reflns_number_total             4656
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5sc03823e2.cif
_cod_data_source_block           s4032ma
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      P2(1)/n
_cod_database_code               1540522