Synthesis of tetrahydrothiopyrano[2,3-b]indoles via [3+3] annulation of nitroallylic acetates with indoline-2-thiones
Basu, Pallabita; Hazra, Chiranjit; Baiju, Thekke V.; Namboothiri, Irishi N. N.; New Journal of Chemistry 44 (2020) 1389–1399; doi:10.1039/C9NJ04754A

data_7059275
_publ_section_title
;
 Synthesis of tetrahydrothiopyrano[2,3-b]indoles via [3+3] annulation of
 nitroallylic acetates with indoline-2-thiones
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1389
_journal_page_last               1399
_journal_paper_doi               10.1039/C9NJ04754A
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C18 H15 Br N2 O2 S'
_chemical_formula_sum            'C18 H15 Br N2 O2 S'
_chemical_formula_weight         403.29
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-20
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.08.26 svn.r3337 for Rigaku Oxford Diffraction, GUI svn.r5221)
;
_audit_update_record
;
2018-11-09 deposited with the CCDC.	2019-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   29.6557(7)
_cell_length_b                   29.6557(7)
_cell_length_c                   9.9045(3)
_cell_measurement_reflns_used    12972
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.1920
_cell_measurement_theta_min      2.2060
_cell_volume                     7543.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -56.00  70.00   0.50   16.00    --  -20.00  72.00  36.00  252
  2  \w    -25.00   5.00   0.50   16.00    --  -20.00   0.00  36.00   60
  3  \w   -109.50  14.00   0.50   16.00    --  -20.00 -72.00  36.00  247
  4  \w    -36.00  -6.00   0.50   16.00    --  -20.00  72.00 -36.00   60
  5  \w   -110.00 -13.00   0.50   16.00    --  -20.00 -72.00-108.00  194
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0217503000
_diffrn_orient_matrix_UB_12      -0.0228381000
_diffrn_orient_matrix_UB_13      0.0258594000
_diffrn_orient_matrix_UB_21      0.0120635000
_diffrn_orient_matrix_UB_22      -0.0146495000
_diffrn_orient_matrix_UB_23      -0.0177696000
_diffrn_orient_matrix_UB_31      0.0120570000
_diffrn_orient_matrix_UB_32      0.0051372000
_diffrn_orient_matrix_UB_33      0.0643415000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19509
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.983
_diffrn_reflns_theta_max         24.983
_diffrn_reflns_theta_min         2.204
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_description       needle
_exptl_crystal_F_000             3672
_exptl_crystal_size_max          0.434
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0307P)^2^+18.5528P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0654
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2678
_reflns_number_total             2950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj04754a2.cif
_cod_data_source_block           INN-PB-86C-1_mo
_cod_depositor_comments          'Adding full bibliography for 7059275.cif.'
_cod_original_cell_volume        7543.6(4)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7059275
_chemical_oxdiff_formula         'C18 H15 Br N2 O2 S'
_reflns_odcompleteness_completeness 94.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.10
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C2(H2), C10(H10), C5(H5), C11(H11), C13(H13), C12(H12)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.548
_oxdiff_exptl_absorpt_empirical_full_min 0.667