Synthesis of thieno[2,3-<i>b</i>]indoles by Cloke-Wilson rearrangement of spiro donor-acceptor cyclopropanes.
Ahashan, Sk Jubayar; Maji, Kousik; Kabir, Syed Ramizul; Dash, Jyotirmayee; Chemical communications (Cambridge, England) 62 (2026) 3861–3865; doi:10.1039/d5cc06215b

data_7135367
_publ_section_title
;
 Synthesis of thieno[2,3-<i>b</i>]indoles by Cloke-Wilson rearrangement of
 spiro donor-acceptor cyclopropanes.
;
_journal_issue                   12
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3861
_journal_page_last               3865
_journal_paper_doi               10.1039/d5cc06215b
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C18 H15 N O S'
_chemical_formula_sum            'C18 H15 N O S'
_chemical_formula_weight         293.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2026-01-16
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2026-01-16 deposited with the CCDC.	2026-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.52230(10)
_cell_length_b                   8.7061(3)
_cell_length_c                   29.2709(9)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    159.91
_cell_measurement_theta_max      33.77
_cell_measurement_theta_min      2.72
_cell_volume                     1407.28(7)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker D8 venture'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      159.91
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            19513
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.747
_diffrn_reflns_theta_min         2.722
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_correction_T_min  0.4559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1493 before and 0.0960 after correction.
The Ratio of minimum to maximum transmission is 0.6105.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_preparation       'SLOW EVAPORATION FROM DICHLOROMETHANE'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1721 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         5240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0472P)^2^+0.2732P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1102
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.800
_reflns_number_gt                4625
_reflns_number_total             5240
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06215b2.cif
_cod_data_source_block           mo_jrg251125a_0m_a
_cod_database_code               7135367
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C00A(H00A), C00B(H00B), C00C(H00C), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J)
1.b Idealised Me refined as rotating group:
 C00K(H00D,H00E,H00K), C00L(H00L,H00M,H00N)
;
_olex2_submission_special_instructions 'No special instructions were received'