Gold(I)-Catalyzed Synthesis of 3-Sulfenyl Pyrroles and Indoles by a Regioselective Annulation of Alkynyl Thioethers
Simm, Peter E.; Sekar, Prakash; Richardson, Jeffery; Davies, Paul W.; ACS Catalysis  (2021) 6357–6362; doi:10.1021/acscatal.1c01457

data_4518710
_publ_section_title
;
 Gold(I)-Catalyzed Synthesis of 3-Sulfenyl Pyrroles and Indoles by a
 Regioselective Annulation of Alkynyl Thioethers
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              6357
_journal_page_last               6362
_journal_paper_doi               10.1021/acscatal.1c01457
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H21 N O S'
_chemical_formula_sum            'C17 H21 N O S'
_chemical_formula_weight         287.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7593(3)
_cell_length_b                   11.1929(4)
_cell_length_c                   20.8815(9)
_cell_measurement_reflns_used    6740
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.1830
_cell_measurement_theta_min      4.1800
_cell_volume                     1579.81(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -62.00 -37.00   1.00    1.17    --  -42.56  38.00  90.00   25
  2  \w   -113.00 -20.00   1.00    1.17    --  -42.56 -38.00  90.00   93
  3  \w    -14.00  25.00   1.00    1.00    --  -42.56  38.00  90.00   39
  4  \w    -97.00 -70.00   1.00    1.00    --  -42.56-148.00-132.00   27
  5  \w    119.00 152.00   1.00    1.00    --  106.63 125.00 -90.00   33
  6  \w     48.00  85.00   1.00    1.00    --  106.63-125.00 -60.00   37
  7  \w     40.00 113.00   1.00    1.00    --  106.63-125.00-120.00   73
  8  \w     27.00 152.00   1.00    1.00    --  106.63 -15.00-180.00  125
  9  \w   -105.00 -54.00   1.00    1.00    --  -43.50 -38.00-180.00   51
 10  \w    100.00 125.00   1.00    1.00    --   43.86 178.00-180.00   25
 11  \w   -116.00 -21.00   1.00    1.00    --  -43.50 -38.00-120.00   95
 12  \w   -129.00 -34.00   1.00    1.00    --  -43.50 178.00 120.00   95
 13  \w    -70.00  -7.00   1.00    1.00    --  -43.50  57.00 120.00   63
 14  \w   -117.00 -12.00   1.00    1.00    --  -43.50 -77.00   0.00  105
 15  \w     55.00  97.00   1.00    1.00    --  106.63-125.00 -30.00   42
 16  \w     51.00  77.00   1.00    1.00    --  106.63 -45.00 120.00   26
 17  \w     81.00 107.00   1.00    1.00    --  106.63 -45.00 120.00   26
 18  \w    131.00 169.00   1.00    1.00    --  106.63  45.00 150.00   38
 19  \w   -117.00 -11.00   1.00    1.06    --  -42.81 -77.00-150.00  106
 20  \w   -113.00 -16.00   1.00    1.06    --  -42.81 -57.00  60.00   97
 21  \w    -27.00  69.00   1.00    1.06    --   42.81 -57.00 120.00   96
 22  \w     25.00  50.00   1.00    1.00    --  106.63 -94.00   0.00   25
 23  \w     83.00 178.00   1.00    1.00    --  106.63  30.00   0.00   95
 24  \w     27.00 152.00   1.00    1.00    --  106.63 -15.00 -30.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0679429000
_diffrn_orient_matrix_UB_12      -0.1243152000
_diffrn_orient_matrix_UB_13      0.0228284000
_diffrn_orient_matrix_UB_21      -0.0431356000
_diffrn_orient_matrix_UB_22      0.0360569000
_diffrn_orient_matrix_UB_23      0.0698409000
_diffrn_orient_matrix_UB_31      -0.2131178000
_diffrn_orient_matrix_UB_32      -0.0469068000
_diffrn_orient_matrix_UB_33      -0.0068045000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14508
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.781
_diffrn_reflns_theta_min         4.234
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.28(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0454P)^2^+0.5750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0973
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                2811
_reflns_number_total             3135
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c01457_si_002.cif
_cod_data_source_block           3j
_cod_original_cell_volume        1579.81(12)
_cod_database_code               4518710
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C17 H21 N1 O1 S1'
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.656
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.72(3)
 0.28(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12)
3.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C),
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              9439
_shelx_hkl_checksum              4443
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.369
_oxdiff_exptl_absorpt_empirical_full_min 0.687