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_4117346
_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 H23 N O3'
_chemical_formula_weight         449.41
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 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                 90.21(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.3780(15)
_cell_length_b                   11.193(2)
_cell_length_c                   41.950(8)
_cell_measurement_temperature    373(2)
_cell_volume                     3464.3(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      373(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.1140
_diffrn_reflns_av_sigmaI/netI    0.1959
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            28067
_diffrn_reflns_theta_full        23.37
_diffrn_reflns_theta_max         23.37
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9721
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.9(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.771
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     957
_refine_ls_number_reflns         9957
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.771
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0638
_refine_ls_shift/su_max          2.682
_refine_ls_shift/su_mean         0.066
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0230P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1149
_reflns_number_gt                4713
_reflns_number_total             9957
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja210793x_si_002.cif
_cod_data_source_block           kevin01t
_cod_depositor_comments
;
 Updated bibliographic information.

 Antanas Vaitkus,
 2019-10-10
;
_cod_original_cell_volume        3464.3(12)
_cod_database_code               4117346