SnCl4-Mediated One-Pot Synthesis of 2,4,5-Trisubstituted Thiazoles from Nitro-Substituted Donor-Acceptor Cyclopropanes and Thioamides
Maniarasu, Meenakshi; Kannupal, Srinivasan; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01604D

data_7158948
_publ_section_title
;
 SnCl4-Mediated One-Pot Synthesis of 2,4,5-Trisubstituted Thiazoles from
 Nitro-Substituted Donor-Acceptor Cyclopropanes and Thioamides
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01604D
_journal_year                    2022
_chemical_formula_sum            'C23 H23 N O5 S'
_chemical_formula_weight         425.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2cx9p9
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-08-17 deposited with the CCDC.	2022-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.509(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7261(9)
_cell_length_b                   26.408(3)
_cell_length_c                   8.5437(7)
_cell_measurement_reflns_used    7611
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      3.09
_cell_volume                     2193.7(4)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3(Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker axs kappa apex3 PHOTON II Diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1746
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            70221
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.602
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker 2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3859
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.1295
_refine_ls_R_factor_gt           0.0924
_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^)+(0.0679P)^2^+3.3812P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1849
_refine_ls_wR_factor_ref         0.2053
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2802
_reflns_number_total             3859
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01604d2.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        2193.7(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7158948
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              90483