Palladium-Catalyzed Approach for the General Synthesis of (E)-2-Arylmethylidene-N-tosylindolines and (E)-2-Arylmethylidene-N-tosyl/nosyltetrahydroquinolines: Access to 2-Substituted Indoles and Quinolines
Chinmay Chowdhury; Bimolendu Das; Sanjukta Mukherjee; Basudeb Achari; Journal of Organic Chemistry 77 (2012) 5108–5119; doi:10.1021/jo300458v

data_4027219
_publ_section_title
;
 Palladium-Catalyzed Approach for the General Synthesis of
 (E)-2-Arylmethylidene-N-tosylindolines and
 (E)-2-Arylmethylidene-N-tosyl/nosyltetrahydroquinolines: Access to
 2-Substituted Indoles and Quinolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5108
_journal_page_last               5119
_journal_paper_doi               10.1021/jo300458v
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         C22H19NO2S
_chemical_formula_sum            'C22 H19 N O2 S'
_chemical_formula_weight         361.44
_chemical_melting_point          401(1)
_chemical_name_common            Indole
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.796(5)
_cell_angle_beta                 74.623(5)
_cell_angle_gamma                86.501(5)
_cell_formula_units_Z            4
_cell_length_a                   9.8549(10)
_cell_length_b                   12.8504(13)
_cell_length_c                   15.1652(15)
_cell_measurement_reflns_used    9866
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.60
_cell_measurement_theta_min      1.39
_cell_volume                     1848.3(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            36753
_diffrn_reflns_theta_full        28.60
_diffrn_reflns_theta_max         28.60
_diffrn_reflns_theta_min         1.39
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.9943
_exptl_absorpt_correction_T_min  0.9830
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       niddle-shaped
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.872
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         9377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.872
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.076
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.9885P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1628
_reflns_number_gt                6928
_reflns_number_total             9377
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300458v_si_003.cif
_cod_data_source_block           snj_3_177_040211_0m
_cod_database_code               4027219