Gold-Catalyzed Cycloisomerizations of 1-(2-(Tosylamino)phenyl)prop-2-yn-1-ols to 1H-Indole-2-carbaldehydes and (E)-2-(Iodomethylene)indolin-3-ols
Prasath Kothandaraman; Srinivasa Reddy Mothe; Sharon Si Min Toh; Philip Wai Hong Chan; Journal of Organic Chemistry 76 (2011) 7633–7640; doi:10.1021/jo201208e

data_4026604
_publ_section_title
;
 Gold-Catalyzed Cycloisomerizations of
 1-(2-(Tosylamino)phenyl)prop-2-yn-1-ols to 1H-Indole-2-carbaldehydes and
 (E)-2-(Iodomethylene)indolin-3-ols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7633
_journal_page_last               7640
_journal_paper_doi               10.1021/jo201208e
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C22 H17 Br I N O3 S'
_chemical_formula_sum            'C22 H17 Br I N O3 S'
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_symmetry_space_group_name_Hall  '-P 1'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 92.440(5)
_cell_angle_gamma                105.731(4)
_cell_formula_units_Z            4
_cell_length_a                   8.5679(8)
_cell_length_b                   9.5677(9)
_cell_length_c                   26.710(3)
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.31
_cell_volume                     2103.2(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
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_computing_molecular_graphics    'Bruker SHELXTL'
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_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
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_diffrn_reflns_limit_l_min       -35
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_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         28.50
_diffrn_reflns_theta_min         1.53
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_exptl_absorpt_correction_T_max  0.6366
_exptl_absorpt_correction_T_min  0.3313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
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_exptl_crystal_description       block
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_refine_diff_density_min         -1.832
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         10375
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_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0695P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1230
_reflns_number_gt                7892
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_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201208e_si_002.cif
_cod_data_source_block           chan129_0m
_cod_original_cell_volume        2103.2(3)
_cod_database_code               4026604