Palladium-catalyzed direct C-H arylations of dioxythiophenes bearing reactive functional groups: a step-economical approach for functional π-conjugated oligoarenes.
Liu, Ching-Yuan; Chong, Hui; Lin, Hsing-An; Yamashita, Yoshiro; Zhang, Bin; Huang, Kuo-Wei; Hashizume, Daizuke; Yu, Hsiao-Hua; Organic & biomolecular chemistry 13 (2015) 8505–8511; doi:10.1039/c5ob00705d

data_7154553
_publ_section_title
;
 Palladium-catalyzed direct C-H arylations of dioxythiophenes bearing
 reactive functional groups: a step-economical approach for functional
 \p-conjugated oligoarenes.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8505
_journal_page_last               8511
_journal_paper_doi               10.1039/c5ob00705d
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C23 H20 O5 S'
_chemical_formula_sum            'C23 H20 O5 S'
_chemical_formula_weight         408.45
_chemical_name_systematic
1,1'-(4,4'-(2-(Hydroxymethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-diyl)bis(4,1-phenylene))diethanone
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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-2013
_audit_update_record
;
2015-03-24 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                86.2826(10)
_cell_angle_beta                 65.3443(12)
_cell_angle_gamma                88.544(3)
_cell_formula_units_Z            4
_cell_length_a                   11.9644(3)
_cell_length_b                   12.3239(4)
_cell_length_c                   13.9643(5)
_cell_measurement_reflns_used    40136
_cell_measurement_temperature    90
_cell_measurement_theta_max      30.256
_cell_measurement_theta_min      1.607
_cell_volume                     1867.35(10)
_computing_cell_refinement       HKL2000
_computing_data_collection       CrystalClear
_computing_data_reduction        HKL2000
_computing_molecular_graphics    SV
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            49996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.256
_diffrn_reflns_theta_min         1.607
_diffrn_source                   'Fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         11069
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0585
_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/[\s^2^(Fo^2^)+(0.0673P)^2^+1.1501P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1575
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7457
_reflns_number_total             11069
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00705d2.cif
_cod_data_source_block           116A-block
_cod_depositor_comments
'Adding full bibliography for 7154552--7154554.cif.'
_cod_database_code               7154553
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2013-3