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_4518711
_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 unk
_chemical_formula_moiety         'C25 H21 N O2'
_chemical_formula_sum            'C25 H21 N O2'
_chemical_formula_weight         367.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 130.407(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.2387(9)
_cell_length_b                   12.2869(2)
_cell_length_c                   10.5907(5)
_cell_measurement_reflns_used    15139
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.4530
_cell_measurement_theta_min      4.6470
_cell_volume                     1906.3(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.996
_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   -115.00 -20.00   1.00    1.00    --  -42.56 -38.00  90.00   95
  2  \w    -65.00  30.00   1.00    1.00    --  -42.56  38.00-180.00   95
  3  \w    -28.00  69.00   1.00    1.00    --   42.56 -57.00 -90.00   97
  4  \w      1.00  82.00   1.00    1.00    --   42.56 -99.00 -90.00   81
  5  \w     11.00 116.00   1.00    1.00    --   42.56  77.00  30.00  105
  6  \w     32.00 130.00   1.00    1.85    --  106.63 -30.00-150.00   98
  7  \w     83.00 178.00   1.00    1.85    --  106.63  45.00 150.00   95
  8  \w     83.00 178.00   1.00    1.85    --  106.63  45.00  30.00   95
  9  \w     79.00 177.00   1.00    1.85    --  106.63  61.00-180.00   98
 10  \w     83.00 178.00   1.00    1.85    --  106.63  30.00 -60.00   95
 11  \w     33.00 138.00   1.00    1.85    --  106.63 -77.00 -60.00  105
 12  \w     83.00 178.00   1.00    1.85    --  106.63  30.00 120.00   95
 13  \w     35.00 118.00   1.00    1.85    --  106.63-125.00  60.00   83
 14  \w     35.00 118.00   1.00    1.85    --  106.63-125.00 -60.00   83
 15  \w     75.00 178.00   1.00    1.85    --  106.63  77.00 -30.00  103
 16  \w   -116.00 -11.00   1.00    1.00    --  -42.56 -77.00-180.00  105
 17  \w   -116.00 -11.00   1.00    1.00    --  -42.56 -77.00  90.00  105
 18  \w   -113.00 -16.00   1.00    1.00    --  -42.56 -57.00-150.00   97
 19  \w    -65.00  30.00   1.00    1.00    --  -42.56  38.00  90.00   95
 20  \w   -113.00 -16.00   1.00    1.00    --  -42.56 -57.00 -60.00   97
 21  \w     83.00 178.00   1.00    1.85    --  106.63  45.00-120.00   95
 22  \w     75.00 178.00   1.00    1.85    --  106.63  77.00  90.00  103
 23  \w     25.00 109.00   1.00    1.85    --  106.63 -94.00 120.00   84
 24  \w     36.00 134.00   1.00    1.85    --  106.63 -61.00 120.00   98
 25  \w     79.00 177.00   1.00    1.85    --  106.63  61.00-150.00   98
 26  \w     79.00 177.00   1.00    1.85    --  106.63  61.00 -60.00   98
 27  \w     79.00 177.00   1.00    1.85    --  106.63  61.00 -90.00   98
 28  \w     79.00 177.00   1.00    1.85    --  106.63  61.00  30.00   98
 29  \w     79.00 177.00   1.00    1.85    --  106.63  61.00-120.00   98
 30  \w     79.00 177.00   1.00    1.85    --  106.63  61.00  60.00   98
 31  \w     11.00 116.00   1.00    1.00    --   42.56  77.00 -30.00  105
;
_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      -0.0553342000
_diffrn_orient_matrix_UB_12      -0.1042327000
_diffrn_orient_matrix_UB_13      -0.0390198000
_diffrn_orient_matrix_UB_21      -0.0351635000
_diffrn_orient_matrix_UB_22      0.0496660000
_diffrn_orient_matrix_UB_23      0.0829960000
_diffrn_orient_matrix_UB_31      -0.0822729000
_diffrn_orient_matrix_UB_32      0.0488397000
_diffrn_orient_matrix_UB_33      -0.1675214000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17791
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.336
_diffrn_reflns_theta_min         4.697
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.707
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light brown'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1697 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3672
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0279
_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^)+(0.0419P)^2^+0.6567P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0708
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_full    0.918
_reflns_Friedel_fraction_max     0.895
_reflns_number_gt                3634
_reflns_number_total             3672
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c01457_si_003.cif
_cod_data_source_block           8a
_cod_database_code               4518711
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C25 H21 N1 O2'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              12957
_shelx_hkl_checksum              19887
_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 1.417
_oxdiff_exptl_absorpt_empirical_full_min 0.865