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_7154552
_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         'C37 H36 O3 S'
_chemical_formula_sum            'C37 H36 O3 S'
_chemical_formula_weight         560.72
_chemical_name_systematic
(5,7-Bis(4'-propylbiphenyl-4-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methanol
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                90
_cell_angle_beta                 97.8403(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1192(2)
_cell_length_b                   11.3017(2)
_cell_length_c                   25.1913(5)
_cell_measurement_reflns_used    45497
_cell_measurement_temperature    90
_cell_measurement_theta_max      30.064
_cell_measurement_theta_min      1.632
_cell_volume                     2854.05(9)
_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 0.996
_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  0.0641
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            44194
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.064
_diffrn_reflns_theta_min         1.632
_diffrn_source                   'Fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         8328
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0665P)^2^+0.7193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5637
_reflns_number_total             8328
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00705d2.cif
_cod_data_source_block           biphenyl
_cod_depositor_comments
'Adding full bibliography for 7154552--7154554.cif.'
_cod_database_code               7154552
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2013-3