Gold-Catalyzed Intermolecular Ynamide Amination-Initiated Aza-Nazarov Cyclization: Access to Functionalized 2-Aminopyrroles.
Shu, Chao; Wang, Yong-Heng; Shen, Cang-Hai; Ruan, Peng-Peng; Lu, Xin; Ye, Long-Wu; Organic letters 18 (2016) 3254–3257; doi:10.1021/acs.orglett.6b01503

data_1543801
_publ_section_title
;
 Gold-Catalyzed Intermolecular Ynamide Amination-Initiated Aza-Nazarov
 Cyclization: Access to Functionalized 2-Aminopyrroles.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3254
_journal_page_last               3257
_journal_paper_doi               10.1021/acs.orglett.6b01503
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C24 H21 Br N2 O2 S'
_chemical_formula_sum            'C24 H21 Br N2 O2 S'
_chemical_formula_weight         481.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-15
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.06 svn.r3119 for OlexSys, GUI svn.r4979)
;
_cell_angle_alpha                90.203(5)
_cell_angle_beta                 105.459(4)
_cell_angle_gamma                116.432(7)
_cell_formula_units_Z            2
_cell_length_a                   9.0001(5)
_cell_length_b                   9.6916(8)
_cell_length_c                   13.9766(5)
_cell_measurement_reflns_used    4340
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      65.6270
_cell_measurement_theta_min      5.1280
_cell_volume                     1041.58(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_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 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
  1 omega   19.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  -30.0000   60.0000 67

  2 omega   37.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7547  -99.0000  120.0000 31

  3 omega   12.00  123.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  -77.0000   60.0000 111

  4 omega   47.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609 -125.0000  -90.0000 73

  5 omega   27.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  -94.0000    0.0000 76

  6 omega   67.00  166.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609   30.0000 -120.0000 99

  7 omega  110.00  154.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  125.0000   30.0000 44

  8 omega  141.00  166.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  125.0000   60.0000 25

  9 omega   97.00  141.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  125.0000  150.0000 44

 10 omega   95.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  125.0000   60.0000 25

 11 omega   66.00  162.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609   45.0000  -30.0000 96

 12 omega    2.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7547  -99.0000  120.0000 31

 13 omega  -49.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7547   37.0000   30.0000 83

 14 omega  -45.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7547   37.0000 -180.0000 32

 15 omega -114.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7547  -57.0000 -120.0000 101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1144562000
_diffrn_orient_matrix_UB_12      -0.0611116000
_diffrn_orient_matrix_UB_13      0.0697066000
_diffrn_orient_matrix_UB_21      0.1562192000
_diffrn_orient_matrix_UB_22      0.1640166000
_diffrn_orient_matrix_UB_23      0.0226295000
_diffrn_orient_matrix_UB_31      -0.0513194000
_diffrn_orient_matrix_UB_32      0.0389838000
_diffrn_orient_matrix_UB_33      0.0893039000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.928
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6078
_diffrn_reflns_point_group_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         65.667
_diffrn_reflns_theta_min         3.314
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.820
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.535
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         3507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0337
_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^)+(0.1000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1135
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3373
_reflns_number_total             3507
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01503_si_002.cif
_cod_data_source_block           sc-160415
_cod_database_code               1543801
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'