Stereoselective synthesis of thiazino[4,3-a]indoles using the thia-Pictet-Spengler reaction of indoles bearing N-tethered thiols and vinylogous thiocarbonates.
Gharpure, Santosh J.; Nanda, Santosh K.; Organic & biomolecular chemistry 14 (2016) 5586–5590; doi:10.1039/c6ob00501b

data_7155031
_publ_section_title
;
 Stereoselective synthesis of thiazino[4,3-a]indoles using the
 thia-Pictet-Spengler reaction of indoles bearing N-tethered thiols and
 vinylogous thiocarbonates.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5586
_journal_page_last               5590
_journal_paper_doi               10.1039/c6ob00501b
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H20 N O S'
_chemical_formula_sum            'C25 H20 N O S'
_chemical_formula_weight         382.48
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-10-17
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2016-01-15 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.730(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.0511(10)
_cell_length_b                   13.583(16)
_cell_length_c                   9.587(11)
_cell_measurement_temperature    100(2)
_cell_volume                     986.9(16)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7495
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         3.08
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_correction_T_min  0.8894
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             402
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.09
_refine_diff_density_max         2.048
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3171
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0867
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1396P)^2^+1.3160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2299
_refine_ls_wR_factor_ref         0.2389
_reflns_number_gt                2716
_reflns_number_total             3171
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob00501b2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
          Adding full bibliography for 7155031.cif.

2018-01-27
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C16.67 H13.33 N0.67 O0.67 S0.67'
_cod_original_formula_weight         254.99
_cod_original_formula_moiety         '0.67(C25 H20 N O S)'
_cod_original_formula_units_Z            3
_cod_database_code               7155031
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Me refined with riding coordinates:
 C23(H23A,H23B,H23C)
2.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C18(H18), C19(H19), C20(H20), C21(H21), C28(H28)
;