Transition-Metal-Free Synthesis of Unsymmetrical Diaryl Chalcogenides from Arenes and Diaryl Dichalcogenides
Ch Durga Prasad; Shah Jaimin Balkrishna; Amit Kumar; Bhagat Singh Bhakuni; Kaustubh Shrimali; Soumava Biswas; Sangit Kumar; Journal of Organic Chemistry 78 (2013) 1434–1443; doi:10.1021/jo302480j

data_4027961
_publ_section_title
;
 Transition-Metal-Free Synthesis of Unsymmetrical Diaryl Chalcogenides
 from Arenes and Diaryl Dichalcogenides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1434
_journal_page_last               1443
_journal_paper_doi               10.1021/jo302480j
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C16 H16 O2 S'
_chemical_formula_weight         272.35
_space_group_IT_number           2
_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
_cell_angle_alpha                83.871(6)
_cell_angle_beta                 84.899(6)
_cell_angle_gamma                73.945(6)
_cell_formula_units_Z            2
_cell_length_a                   7.6506(8)
_cell_length_b                   8.0881(9)
_cell_length_c                   11.7507(13)
_cell_measurement_temperature    130(2)
_cell_volume                     693.42(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      130(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12588
_diffrn_reflns_theta_full        28.91
_diffrn_reflns_theta_max         28.91
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_process_details   empirical
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       Block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.311
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.311
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1754
_reflns_number_gt                2927
_reflns_number_total             3542
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302480j_si_002.cif
_cod_data_source_block           SKumar
_cod_database_code               4027961