A Unified Route to the Welwitindolinone Alkaloids: Total Syntheses of (-)-N-Methylwelwitindolinone C Isothiocyanate, (-)-N-Methylwelwitindolinone C Isonitrile, and (-)-3-Hydroxy-N-methylwelwitindolinone C Isothiocyanate
Allan, Kevin M.; Kobayashi, Kenichi; Rawal, Viresh H.; Journal of the American Chemical Society 134 (2012) 1392–1395; doi:10.1021/ja210793x

data_4117347
_publ_section_title
;
 A Unified Route to the Welwitindolinone Alkaloids: Total Syntheses of
 (-)-N-Methylwelwitindolinone C Isothiocyanate,
 (-)-N-Methylwelwitindolinone C Isonitrile, and
 (-)-3-Hydroxy-N-methylwelwitindolinone C Isothiocyanate
;
_journal_coden_ASTM              JACSAT
_journal_issue                   3
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1392
_journal_page_last               1395
_journal_paper_doi               10.1021/ja210793x
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C22 H21 Cl N2 O3 S'
_chemical_formula_weight         428.92
_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                 121.670(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.482(2)
_cell_length_b                   20.878(5)
_cell_length_c                   11.974(2)
_cell_measurement_temperature    293(2)
_cell_volume                     2017.4(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_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  0.0895
_diffrn_reflns_av_sigmaI/netI    0.1301
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23928
_diffrn_reflns_theta_full        28.54
_diffrn_reflns_theta_max         28.54
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_T_max  0.9506
_exptl_absorpt_correction_T_min  0.9272
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.796
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.796
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0582
_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^)+(0.0432P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1180
_reflns_number_gt                2471
_reflns_number_total             4963
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja210793x_si_003.cif
_cod_data_source_block           kevin03s
_cod_depositor_comments
;
 Updated bibliographic information.

 Antanas Vaitkus,
 2019-10-10
;
_cod_original_cell_volume        2017.4(7)
_cod_database_code               4117347