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_4516153
_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         'C28 H33 N3 O4 S'
_chemical_formula_sum            'C28 H33 N3 O4 S'
_chemical_formula_weight         507.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-05-12
_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                 108.034(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.959(5)
_cell_length_b                   8.470(2)
_cell_length_c                   21.482(6)
_cell_measurement_reflns_used    8202
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.2
_cell_measurement_theta_min      3.1
_cell_volume                     2761.1(13)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_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
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
scan:
	Number of images: 326
	           Slice: -110.0000 - 53.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: -108.0000
	             XTD: 44.9804
	          2theta: -19.9684
scan:
	Number of images: 153
	           Slice: -57.5000 - 19.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -180.0000
	             XTD: 44.9804
	          2theta: -19.9684
scan:
	Number of images: 60
	           Slice: -64.0000 - -34.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: -180.0000
	             XTD: 44.9804
	          2theta: -19.9684
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: -36.0000
	             XTD: 44.9804
	          2theta: -19.9684
scan:
	Number of images: 138
	           Slice: -63.0000 - 6.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 108.0000
	             XTD: 44.9804
	          2theta: -19.9684
scan:
	Number of images: 60
	           Slice: -44.0000 - -14.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 36.0000
	             XTD: 44.9804
	          2theta: -19.9684
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
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Rigaku Saturn724+ (4x4 bin mode)
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_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
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_diffrn_orient_matrix_UB_11      0.013148
_diffrn_orient_matrix_UB_12      -0.025287
_diffrn_orient_matrix_UB_13      -0.059418
_diffrn_orient_matrix_UB_21      0.113778
_diffrn_orient_matrix_UB_22      -0.010587
_diffrn_orient_matrix_UB_23      0.029684
_diffrn_orient_matrix_UB_31      -0.005231
_diffrn_orient_matrix_UB_32      -0.048599
_diffrn_orient_matrix_UB_33      0.002716
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            37563
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.241
_diffrn_reflns_theta_max         29.165
_diffrn_reflns_theta_min         3.067
_diffrn_source                   MicroMax003_Mo
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         7432
_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0545
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0535P)^2^+0.4166P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1290
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6058
_reflns_number_total             7432
_reflns_shell_number_unique_all  7915
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b02147_si_003.cif
_cod_data_source_block           shelxl
_cod_database_code               4516153
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.948
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C26(H26), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C16(H16), C13(H13), C12(H12), C9(H9), C17(H17), C19(H19),
 C18(H18)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C23(H23A,H23B,H23C), C1(H1A,H1B,H1C), C28(H28A,H28B,
 H28C), C2(H2A,H2B,H2C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              72709
_shelx_hkl_checksum              59498
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'