Access to thiazoline and spiro[indoline-3,3'-thiophene] scaffolds <i>via</i> a formal [3 + 2] annulation reaction of crotonate-derived sulfur ylides and β-ketothioamides.
Zheng, Jing; Gu, Hong; Chen, Qinfang; Yang, Weiran; Organic & biomolecular chemistry 21 (2023) 2069–2080; doi:10.1039/d3ob00087g

data_7159138
_publ_section_title
;
 Access to thiazoline and spiro[indoline-3,3'-thiophene] scaffolds
 <i>via</i> a formal [3 + 2] annulation reaction of crotonate-derived
 sulfur ylides and &#x3b2;-ketothioamides.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2069
_journal_page_last               2080
_journal_paper_doi               10.1039/d3ob00087g
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C20 H19 N O3 S'
_chemical_formula_weight         353.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-07-29 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                69.255(12)
_cell_angle_beta                 76.260(14)
_cell_angle_gamma                89.585(14)
_cell_formula_units_Z            2
_cell_length_a                   9.424(4)
_cell_length_b                   9.886(4)
_cell_length_c                   10.482(4)
_cell_measurement_reflns_used    4776
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.46
_cell_volume                     883.9(6)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.961
_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  0.0264
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8429
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_min         2.233
_exptl_absorpt_coefficient_mu    0.202
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0778P)^2^+0.5926P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.1548
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3610
_reflns_number_total             4233
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00087g2.cif
_cod_data_source_block           20200529LI_ZNZ4932_0m_a
_cod_depositor_comments
'Adding full bibliography for 7159138--7159139.cif.'
_cod_original_cell_volume        884.0(6)
_cod_database_code               7159138
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              80493