Synthesis of Functionalized Thieno[2,3-<i>b</i>]indoles via One-Pot Reaction of Indoline-2-thiones with Morita-Baylis-Hillman and Rauhut-Currier Adducts of Nitroalkenes.
Mane, Vaijinath; Baiju, Thekke V.; Namboothiri, Irishi N. N.; ACS omega 3 (2018) 17617–17628; doi:10.1021/acsomega.8b02147

data_4516152
_publ_section_title
;
 Synthesis of Functionalized Thieno[2,3-<i>b</i>]indoles via One-Pot
 Reaction of Indoline-2-thiones with Morita-Baylis-Hillman and
 Rauhut-Currier Adducts of Nitroalkenes.
;
_journal_issue                   12
_journal_name_full               'ACS omega'
_journal_page_first              17617
_journal_page_last               17628
_journal_paper_doi               10.1021/acsomega.8b02147
_journal_volume                  3
_journal_year                    2018
_chemical_formula_moiety         'C22 H21 N O2 S'
_chemical_formula_sum            'C22 H21 N O2 S'
_chemical_formula_weight         363.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-05-11
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.10.28 svn.r3245 for OlexSys, GUI svn.r5128)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.281(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8883(3)
_cell_length_b                   7.4114(3)
_cell_length_c                   20.6224(7)
_cell_measurement_reflns_used    6983
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.9880
_cell_measurement_theta_min      2.0820
_cell_volume                     1809.31(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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   -110.00  19.00   0.50    8.00    --  -20.00 -72.00-108.00  258
  2  \w    -64.00  52.50   0.50    8.00    --  -20.00   0.00  36.00  233
  3  \w    -30.00 -23.00   0.50    8.00    --  -20.00  72.00-180.00   14
;
_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      0.0349066000
_diffrn_orient_matrix_UB_12      0.0066148000
_diffrn_orient_matrix_UB_13      0.0297025000
_diffrn_orient_matrix_UB_21      -0.0486848000
_diffrn_orient_matrix_UB_22      0.0081114000
_diffrn_orient_matrix_UB_23      0.0172660000
_diffrn_orient_matrix_UB_31      -0.0017028000
_diffrn_orient_matrix_UB_32      -0.0951231000
_diffrn_orient_matrix_UB_33      0.0035222000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8097
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.988
_diffrn_reflns_theta_max         24.988
_diffrn_reflns_theta_min         1.983
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.334
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.147
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0501P)^2^+0.8283P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2894
_reflns_number_total             3169
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b02147_si_004.cif
_cod_data_source_block           inn-mvd-611_mo
_cod_original_cell_volume        1809.31(10)
_cod_database_code               4516152
_chemical_oxdiff_formula         'C22 H21 N1 O2 S1'
_reflns_odcompleteness_completeness 87.45
_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 Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C14(H14), C6(H6), C5(H5), C4(H4), C3(H3), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C22(H22A,H22B,H22C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              51826
_shelx_hkl_checksum              84986
_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 1.527
_oxdiff_exptl_absorpt_empirical_full_min 0.823