Gold-catalyzed generation of azafulvenium from an enyne sulfonamide: rapid access to fully substituted pyrroles
Wu, Feng; Chen, Lianfen; Wang, Yongdong; Zhu, Shifa; Organic Chemistry Frontiers 6 (2019) 480–; doi:10.1039/C8QO01278D

data_1554557
_publ_section_title
;
 Gold-catalyzed generation of azafulvenium from an enyne sulfonamide:
 rapid access to fully substituted pyrroles
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              480
_journal_paper_doi               10.1039/C8QO01278D
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C21 H21 N O2 S'
_chemical_formula_sum            'C21 H21 N O2 S'
_chemical_formula_weight         351.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2018-04-12 deposited with the CCDC.
2019-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.752(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.1655(5)
_cell_length_b                   8.49460(10)
_cell_length_c                   13.3472(2)
_cell_measurement_reflns_used    5441
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4240
_cell_measurement_theta_min      4.0800
_cell_volume                     3492.37(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_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     13.00 116.00   1.00    1.00    --   40.98  77.00   0.00  103
  2  \w     92.00 138.00   1.00    1.00    --  106.95  45.00-150.00   46
  3  \w    106.00 161.00   1.00    1.00    --  106.95 125.00-180.00   55
  4  \w     36.00 135.00   1.00    1.00    --  106.95 -61.00  60.00   99
  5  \w     61.00 108.00   1.00    1.00    --  106.95 -94.00 -30.00   47
  6  \w     55.00  81.00   1.00    1.00    --  106.95 -94.00 -90.00   26
  7  \w     24.00 107.00   1.00    1.00    --  106.95 -94.00-120.00   83
  8  \w     85.00 171.00   1.00    1.00    --  106.95  45.00 150.00   86
  9  \w    -32.00  -5.00   1.00    1.00    --  -40.98 125.00-180.00   27
 10  \w    -64.00  28.00   1.00    1.00    --  -40.98  37.00 -30.00   92
 11  \w    -86.00 -60.00   1.00    1.00    --  -40.98 125.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0078630000
_diffrn_orient_matrix_UB_12      0.1250332000
_diffrn_orient_matrix_UB_13      0.0845307000
_diffrn_orient_matrix_UB_21      -0.0004668000
_diffrn_orient_matrix_UB_22      -0.1297325000
_diffrn_orient_matrix_UB_23      0.0804545000
_diffrn_orient_matrix_UB_31      0.0493689000
_diffrn_orient_matrix_UB_32      -0.0207924000
_diffrn_orient_matrix_UB_33      0.0052709000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6848
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.559
_diffrn_reflns_theta_min         5.402
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.753
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+3.0347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1111
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3310
_reflns_number_total             3443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01278d2.cif
_cod_data_source_block           exp_316
_cod_database_code               1554557
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.767
_shelx_estimated_absorpt_t_min   0.668
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C20(H20), C9(H9), C16(H16), C10(H10), C19(H19), C12(H12), C17(H17),
 C11(H11)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;
_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 1.390
_oxdiff_exptl_absorpt_empirical_full_min 0.714