Thio-Michael addition of thioamides and allenes for the selective construction of polysubstituted 2-arylthiophenes via TBAI/H<sub>2</sub>O<sub>2</sub> promoted tandem oxidative annulation and 1,2-sulfur migration.
Han, Teng; Luo, Xiaoyan; Organic & biomolecular chemistry 16 (2018) 8253–8257; doi:10.1039/c8ob01835a

data_7156396
_publ_section_title
;
 Thio-Michael addition of thioamides and allenes for the selective
 construction of polysubstituted 2-arylthiophenes via
 TBAI/H<sub>2</sub>O<sub>2</sub> promoted tandem oxidative annulation and
 1,2-sulfur migration.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8253
_journal_page_last               8257
_journal_paper_doi               10.1039/c8ob01835a
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C17 H19 N O4 S'
_chemical_formula_sum            'C17 H19 N O4 S'
_chemical_formula_weight         333.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-07-19 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.818(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.538(5)
_cell_length_b                   6.0233(19)
_cell_length_c                   37.422(12)
_cell_measurement_reflns_used    2570
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.248
_cell_measurement_theta_min      2.640
_cell_volume                     3477.6(19)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            12121
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.192
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0567 before and 0.0399 after correction. The Ratio of minimum to maximum transmission is 0.8931. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3425
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0710
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0699P)^2^+4.2154P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.1908
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1946
_reflns_number_total             3425
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01835a2.cif
_cod_data_source_block           dm17469
_cod_depositor_comments          'Adding full bibliography for 7156396.cif.'
_cod_original_cell_volume        3477.7(19)
_cod_database_code               7156396
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.976
_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. Uiso/Uaniso restraints and constraints
O3 \\sim C16 \\sim C16': within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002
3. Others
 Fixed Sof: O4(0.5) C15(0.5) H15A(0.5) H15B(0.5) C16(0.5) C17(0.5) H17A(0.5)
 H17B(0.5) H17C(0.5) O4'(0.5) C15'(0.5) H15C(0.5) H15D(0.5) C16'(0.5) C17'(0.5)
 H17D(0.5) H17E(0.5) H17F(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C15'(H15C,H15D)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
4.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C17(H17A,H17B,
 H17C), C17'(H17D,H17E,H17F)
;
_shelx_res_checksum              15692
_olex2_submission_special_instructions 'No special instructions were received'