Palladium-catalyzed, unsymmetrical homocoupling of thiophenes via carbon–sulfur bond activation: a new avenue to homocoupling reactions
Vahabi, Amir Hossein; Alizadeh, Abdolali; Khavasi, Hamid Reza; Bazgir, Ayoob; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01923H

data_7155868
_publ_section_title
;
 Palladium-catalyzed, unsymmetrical homocoupling of thiophenes via
 carbon--sulfur bond activation: a new avenue to homocoupling reactions
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01923H
_journal_year                    2017
_chemical_formula_sum            'C25 H16 N4 O2 S3'
_chemical_formula_weight         500.63
_space_group_IT_number           2
_symmetry_cell_setting           Triiclinic
_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
;
2017-05-21 deposited with the CCDC.
2017-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                80.068(19)
_cell_angle_beta                 88.626(19)
_cell_angle_gamma                82.085(19)
_cell_formula_units_Z            2
_cell_length_a                   6.4503(16)
_cell_length_b                   12.709(3)
_cell_length_c                   16.510(4)
_cell_measurement_reflns_used    12119
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.50
_cell_volume                     1320.5(6)
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2332
_diffrn_reflns_av_sigmaI/netI    0.3177
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12119
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.9821
_exptl_absorpt_correction_T_min  0.9650
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'shape of crystal determined optically'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.3047
_refine_ls_R_factor_gt           0.1350
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1078P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2636
_refine_ls_wR_factor_ref         0.3210
_reflns_number_gt                1851
_reflns_number_total             5763
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob01923h2.cif
_cod_data_source_block           khc1099
_cod_original_cell_volume        1320.4(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7155868