Organocatalytic asymmetric [4 + 4]-annulation reaction between ynones and benzylidene thiazolones: Synthesis of eight-membered ether containing 4,5-fused thiazoles
Barman, Dipankar; Pan, Subhas Chandra; Chemical Communications  (2026) –; doi:10.1039/D6CC01689H

data_7135749
_publ_section_title
;
 Organocatalytic asymmetric [4+4]-annulation reaction between ynones and
 benzylidene thiazolones: synthesis of eight-membered ether containing
 4,5-fused thiazoles.
;
_journal_issue                   36
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9285
_journal_page_last               9288
_journal_paper_doi               10.1039/d6cc01689h
_journal_volume                  62
_journal_year                    2026
_chemical_absolute_configuration 6S,7S
_chemical_formula_sum            'C32 H22 Br N O2 S'
_chemical_formula_weight         564.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-12-16 deposited with the CCDC.	2026-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.221(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.475(6)
_cell_length_b                   11.186(7)
_cell_length_c                   13.604(9)
_cell_measurement_reflns_used    8156
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      21.81
_cell_measurement_theta_min      2.33
_cell_volume                     1377.2(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            33563
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.567
_exptl_absorpt_coefficient_mu    1.597
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       Block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 1596 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.064(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4834
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0828P)^2^+0.0976P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1378
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3822
_reflns_number_total             4834
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc01689h2.cif
_cod_data_source_block           db_thia_2br_2_0m_a
_cod_depositor_comments          'Adding full bibliography for 7135749.cif.'
_cod_original_cell_volume        1377.3(15)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7135749
_shelx_shelxl_version_number     2019/3
_shelx_res_checksum              1661
_shelx_hkl_checksum              94961