Palladium-Catalyzed Iodine-Mediated Electrophilic Annulation of 2-(1-Alkynyl)biphenyls with Disulfides
Bo-Lun Hu; Sha-Sha Pi; Peng-Cheng Qian; Jin-Heng Li; Xing-Guo Zhang; Journal of Organic Chemistry 78 (2013) 1300–1305; doi:10.1021/jo302634n

data_4027932
_publ_section_title
;
 Palladium-Catalyzed Iodine-Mediated Electrophilic Annulation of
 2-(1-Alkynyl)biphenyls with Disulfides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1300
_journal_page_last               1305
_journal_paper_doi               10.1021/jo302634n
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C26 H18 S'
_chemical_formula_sum            'C26 H18 S'
_chemical_formula_weight         362.46
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_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
_cell_angle_alpha                90.00
_cell_angle_beta                 98.725(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.584(3)
_cell_length_b                   10.879(3)
_cell_length_c                   16.559(4)
_cell_measurement_reflns_used    2715
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.212
_cell_measurement_theta_min      2.246
_cell_volume                     1884.6(9)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL(Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX area-detector diffractometer'
_diffrn_measurement_method       '\f and \w scan'
_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  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9592
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.9737
_exptl_absorpt_correction_T_min  0.9533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       Block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.227
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0675
_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^)+(0.0474P)^2^+1.1109P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1433
_reflns_number_gt                2994
_reflns_number_total             3305
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo302634n_si_002.cif
_cod_data_source_block           12172m
_cod_original_cell_volume        1884.5(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4027932