Lewis base-catalyzed cascade [4 + 2]-annulation reaction of <i>N</i>-alkoxy acrylamides and acyl isothiocyanates: facile access to 2-imino-1,3-thiazinone derivatives.
Wang, Zhaoxue; Tian, Ge; Shi, Yuying; Liu, Wanxing; Xu, Xiangdong; Li, Xiaojing; Wu, Lingang; Xie, Lei; Organic & biomolecular chemistry 21 (2023) 9200–9209; doi:10.1039/d3ob01440a

data_7159625
_publ_section_title
;
 Lewis base-catalyzed cascade [4 + 2]-annulation reaction of
 <i>N</i>-alkoxy acrylamides and acyl isothiocyanates: facile access to
 2-imino-1,3-thiazinone derivatives.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9200
_journal_page_last               9209
_journal_paper_doi               10.1039/d3ob01440a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C19 H18 N2 O3 S'
_chemical_formula_sum            'C19 H18 N2 O3 S'
_chemical_formula_weight         354.41
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-31
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2023-09-05 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.3890(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.264(3)
_cell_length_b                   6.0091(5)
_cell_length_c                   19.0987(17)
_cell_measurement_reflns_used    5324
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.364
_cell_measurement_theta_min      2.694
_cell_volume                     3470.8(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9891
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.364
_diffrn_reflns_theta_min         2.857
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1022 before and 0.0293 after correction.
The Ratio of minimum to maximum transmission is 0.9179.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0401P)^2^+2.1809P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0876
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3377
_reflns_number_total             3885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01440a2.cif
_cod_data_source_block           230729xl_0m
_cod_depositor_comments          'Adding full bibliography for 7159625.cif.'
_cod_original_cell_volume        3470.9(5)
_cod_database_code               7159625
_shelx_shelxl_version_number     2018/3
_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.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C13(H13), C15(H15),
 C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_shelx_res_checksum              11043
_olex2_submission_special_instructions 'No special instructions were received'