Rhodium-Catalyzed Synthesis of Unsymmetric Di(heteroaryl) Sulfides Using Heteroaryl Ethers and S-Heteroaryl Thioesters via Heteroarylthio Exchange.
Arisawa, Mieko; Tazawa, Takeru; Tanii, Saori; Horiuchi, Kiyofumi; Yamaguchi, Masahiko; The Journal of organic chemistry 82 (2017) 804–810; doi:10.1021/acs.joc.6b02585

data_4032212
_publ_section_title
;
 Rhodium-Catalyzed Synthesis of Unsymmetric Di(heteroaryl) Sulfides Using
 Heteroaryl Ethers and S-Heteroaryl Thioesters via Heteroarylthio
 Exchange.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              804
_journal_page_last               810
_journal_paper_doi               10.1021/acs.joc.6b02585
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C11 H6 Cl N O S2'
_chemical_formula_weight         267.74
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.1851(5)
_cell_length_b                   9.0849(5)
_cell_length_c                   8.6746(7)
_cell_measurement_reflns_used    6598
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      3.05
_cell_volume                     1117.90(12)
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SHELXD
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS Rapid'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_av_sigmaI/netI    0.0733
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10404
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         3.55
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.146
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.08(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2544
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0953P)^2^+1.0378P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1993
_reflns_number_gt                1678
_reflns_number_total             2544
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02585_si_003.cif
_cod_data_source_block           ydkr
_cod_database_code               4032212