Aryl Methyl Sulfides as Substrates for Rhodium-Catalyzed Alkyne Carbothiolation: Arene Functionalization with Activating Group Recycling
Joel F. Hooper; Adrian B. Chaplin; Carlos González-Rodríguez; Amber L. Thompson; Andrew S. Weller; Michael C. Willis; Journal of the American Chemical Society 134 (2012) 2906–2909; doi:10.1021/ja2108992

data_4117462
_publ_contact_author             'Michael C. Willis & Andrew S. Weller'
_publ_contact_author_email
'michael.willis@chem.ox.ac.uk & andrew.weller@chem.ox.ac.uk'
_publ_section_title
;
 Aryl Methyl Sulfides as Substrates for Rhodium-Catalyzed Alkyne
 Carbothiolation: Arene Functionalization with Activating Group Recycling
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2906
_journal_page_last               2909
_journal_paper_doi               10.1021/ja2108992
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C18 H19 O S, C F3 O3 S'
_chemical_formula_sum            'C19 H19 F3 O4 S2'
_chemical_formula_weight         432.48
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             12-01-26
_audit_creation_method           CRYSTALS_ver_14.40
_cell_angle_alpha                90
_cell_angle_beta                 93.583(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0680(11)
_cell_length_b                   22.5648(18)
_cell_length_c                   7.3024(7)
_cell_measurement_reflns_used    1617
_cell_measurement_temperature    150
_cell_measurement_theta_max      77
_cell_measurement_theta_min      4
_cell_volume                     1984.6(3)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.167
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13321
_diffrn_reflns_theta_full        72.746
_diffrn_reflns_theta_max         77.390
_diffrn_reflns_theta_min         3.918
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.896
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.73
_refine_diff_density_min         -0.77
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2692
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0723
_refine_ls_shift/su_max          0.0001829
_refine_ls_shift/su_mean         0.0000239
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.09P)^2^ + 0.00P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2064
_refine_ls_wR_factor_gt          0.1743
_refine_ls_wR_factor_ref         0.2064
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              27
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                1684
_reflns_number_total             4092
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.17
_oxford_diffrn_Wilson_scale      0.52
_oxford_refine_ls_r_factor_ref   0.1094
_oxford_refine_ls_scale          1.481(19)
_oxford_reflns_number_all        2692
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 6419
_cod_data_source_file            ja2108992_si_002_4.cif
_cod_data_source_block           8
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4117462
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 143,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 192,X'S) H   ( 193,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 202,X'S) H   ( 201,X'S) H   ( 203,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;