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_1554558
_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 H18 Br N O3 S'
_chemical_formula_sum            'C21 H18 Br N O3 S'
_chemical_formula_weight         444.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-12 deposited with the CCDC.
2019-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.769(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6549(5)
_cell_length_b                   18.2100(11)
_cell_length_c                   11.9124(6)
_cell_measurement_reflns_used    5668
_cell_measurement_temperature    172.95(10)
_cell_measurement_theta_max      73.6420
_cell_measurement_theta_min      3.7400
_cell_volume                     1870.96(18)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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      172.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.962
_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    -19.00  25.00   0.50    0.50    --    0.00 -77.00-150.00   88
  2  \w      6.00  88.00   0.50    0.50    --    0.00  19.00 -30.00  164
  3  \w    -86.00 -42.00   0.50    0.50    --    0.00 -77.00-150.00   88
  4  \w    -57.00 -32.00   0.50    0.50    --    0.00 -38.00-180.00   50
  5  \w     75.00 134.00   0.50    0.50    --   95.20  61.00 120.00  118
  6  \w     61.00  89.00   0.50    0.50    --   95.20 -30.00 -60.00   56
  7  \w      9.00  70.00   0.50    0.50    --   95.20 -61.00 -90.00  122
  8  \w    157.00 183.00   0.50    0.50    --   95.20  30.00   0.00   52
  9  \w     80.00 139.00   0.50    0.50    --   95.20  30.00   0.00  118
 10  \w     16.00 107.00   0.50    0.50    --   95.20 -77.00 -90.00  182
 11  \w     75.00 119.00   0.50    0.50    --   95.20 -61.00 -90.00   88
 12  \w     10.00  44.00   0.50    0.50    --   95.20 -30.00 -60.00   68
 13  \w     89.00 163.00   0.50    0.50    --   95.20  82.00  90.00  148
 14  \w     92.00 177.00   0.50    0.50    --   95.20  30.00  30.00  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0876242000
_diffrn_orient_matrix_UB_12      -0.0603833000
_diffrn_orient_matrix_UB_13      0.0701141000
_diffrn_orient_matrix_UB_21      0.1466177000
_diffrn_orient_matrix_UB_22      0.0481972000
_diffrn_orient_matrix_UB_23      0.0099537000
_diffrn_orient_matrix_UB_31      -0.0520303000
_diffrn_orient_matrix_UB_32      0.0346058000
_diffrn_orient_matrix_UB_33      0.1087102000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9309
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.477
_diffrn_reflns_theta_min         4.446
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.223
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.307
_refine_diff_density_min         -1.536
_refine_diff_density_rms         0.155
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3679
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0759
_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^)+(0.1740P)^2^+1.3174P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2101
_refine_ls_wR_factor_ref         0.2302
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3093
_reflns_number_total             3679
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01278d2.cif
_cod_data_source_block           20171013
_cod_database_code               1554558
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.631
_shelx_estimated_absorpt_t_min   0.551
_reflns_odcompleteness_completeness 99.74
_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:
 C12(H12), C13(H13), C19(H19), C9(H9), C15(H15), C10(H10), C18(H18), C21(H21),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 4.706
_oxdiff_exptl_absorpt_empirical_full_min 0.332