Silver Acetate Catalyzed Hydroamination of 1-(2-(Sulfonylamino)phenyl)prop-2-yn-1-ols to (Z)-2-Methylene-1-sulfonylindolin-3-ols
Dewi Susanti; Fujiet Koh; Jeffrey Antonius Kusuma; Prasath Kothandaraman; Philip Wai Hong Chan; Journal of Organic Chemistry 77 (2012) 7166–7175; doi:10.1021/jo301198z

data_4027451
_publ_section_title
;
 Silver Acetate Catalyzed Hydroamination of
 1-(2-(Sulfonylamino)phenyl)prop-2-yn-1-ols to
 (Z)-2-Methylene-1-sulfonylindolin-3-ols
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7166
_journal_page_last               7175
_journal_paper_doi               10.1021/jo301198z
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C22 H18 I N O3 S'
_chemical_formula_sum            'C22 H18 I N O3 S'
_chemical_formula_weight         503.33
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 129.9040(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2734(3)
_cell_length_b                   17.7404(4)
_cell_length_c                   14.0160(3)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      33.16
_cell_measurement_theta_min      2.58
_cell_volume                     1959.59(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            31818
_diffrn_reflns_theta_full        33.29
_diffrn_reflns_theta_max         33.29
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    1.764
_exptl_absorpt_correction_T_max  0.6021
_exptl_absorpt_correction_T_min  0.5388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         7517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0230
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0206P)^2^+1.0036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0515
_refine_ls_wR_factor_ref         0.0532
_reflns_number_gt                6667
_reflns_number_total             7517
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301198z_si_001.cif
_cod_data_source_block           chan171
_cod_original_cell_volume        1959.59(8)
_cod_database_code               4027451