Gold-catalyzed cascade cyclization of N-propargyl ynamides: rapid access to functionalized indeno[1,2-c]pyrroles
Shen, Wen-Bo; Zhou, Bo; Zhang, Zhi-Xin; Yuan, Han; Fang, Wei; Ye, Long-Wu; Organic Chemistry Frontiers 5 (2018) 2468–; doi:10.1039/C8QO00552D

data_1554366
_publ_section_title
;
 Gold-catalyzed cascade cyclization of N-propargyl ynamides: rapid access
 to functionalized indeno[1,2-c]pyrroles
;
_journal_issue                   16
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2468
_journal_paper_doi               10.1039/C8QO00552D
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C18 H15 N O2 S'
_chemical_formula_sum            'C18 H15 N O2 S'
_chemical_formula_weight         309.37
_chemical_name_systematic
2-(methylsulfonyl)-8-phenyl-2,8-dihydroindeno[1,2-c]pyrrole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2018-05-29 deposited with the CCDC.
2018-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.936(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.6922(9)
_cell_length_b                   5.4470(3)
_cell_length_c                   14.5323(7)
_cell_measurement_reflns_used    3024
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      65.9040
_cell_measurement_theta_min      6.0730
_cell_volume                     1477.68(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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details
;
  1 omega   62.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609   61.0000  120.0000 96

  2 omega  104.00  155.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  125.0000   90.0000 51

  3 omega  137.00  166.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  149.0000   98.0000 29

  4 omega   95.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  123.0000  -63.0000 42

  5 omega  134.00  166.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  125.0000 -180.0000 32

  6 omega   16.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  -30.0000    0.0000 68

  7 omega   34.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       91.1609  -94.0000 -150.0000 69

  8 omega    4.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5672  -99.0000   60.0000 42

  9 omega  -86.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5672  125.0000   30.0000 29

 10 omega -116.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5672  -77.0000  150.0000 98
;
_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      -0.0282326000
_diffrn_orient_matrix_UB_12      0.0691900000
_diffrn_orient_matrix_UB_13      -0.0980392000
_diffrn_orient_matrix_UB_21      -0.0009361000
_diffrn_orient_matrix_UB_22      0.2729131000
_diffrn_orient_matrix_UB_23      0.0277832000
_diffrn_orient_matrix_UB_31      0.0775516000
_diffrn_orient_matrix_UB_32      0.0284252000
_diffrn_orient_matrix_UB_33      -0.0295071000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.931
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4684
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         65.820
_diffrn_reflns_theta_min         4.738
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.997
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68352
_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_density_diffrn    1.391
_exptl_crystal_F_000             648
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and ethyl acetate'
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0607P)^2^+1.7393P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1198
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2385
_reflns_number_total             2493
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00552d2.cif
_cod_data_source_block           exp_7568
_cod_original_cell_volume        1477.69(12)
_cod_database_code               1554366
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.576
_shelx_estimated_absorpt_t_min   0.495
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_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 Ternary CH refined with riding coordinates:
 C009(H009)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L)
2.c Idealised Me refined as rotating group:
 C00M(H00B,H00M,H00N)
;
_shelx_res_checksum              46733
_shelx_hkl_checksum              46638
_olex2_date_sample_data_collection 2015-12-07
_olex2_submission_special_instructions 'No special instructions were received'