Synthesis of 2,4,5-Trisubstituted Oxazoles with Complementary Regioselectivity from α-Oxoketene Dithioacetals and β-(Methylthio)-β-(het)aryl-2-propenones.
Kumar, Siripuram Vijay; Acharya, Anand; Ila, Hiriyakkanavar; The Journal of organic chemistry 83 (2018) 6607–6622; doi:10.1021/acs.joc.8b00900

data_4035837
_publ_section_title
;
 Synthesis of 2,4,5-Trisubstituted Oxazoles with Complementary
 Regioselectivity from \a-Oxoketene Dithioacetals and
 \b-(Methylthio)-\b-(het)aryl-2-propenones.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6607
_journal_page_last               6622
_journal_paper_doi               10.1021/acs.joc.8b00900
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C15 H16 Cl N O2 S'
_chemical_formula_sum            'C15 H16 Cl N O2 S'
_chemical_formula_weight         309.80
_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_creation_date             2014-07-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.89(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.187(5)
_cell_length_b                   5.857(2)
_cell_length_c                   20.280(9)
_cell_measurement_reflns_used    1878
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.01
_cell_measurement_theta_min      3.11
_cell_volume                     1555.0(11)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.690
_diffrn_measured_fraction_theta_max 0.715
_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  0.0770
_diffrn_reflns_av_unetI/netI     0.1048
_diffrn_reflns_Laue_measured_fraction_full 0.690
_diffrn_reflns_Laue_measured_fraction_max 0.715
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5739
_diffrn_reflns_point_group_measured_fraction_full 0.690
_diffrn_reflns_point_group_measured_fraction_max 0.715
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.976
_diffrn_reflns_theta_min         1.555
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.380
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1415 before and 0.0918 after correction.
The Ratio of minimum to maximum transmission is 0.6007.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             648
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       0.008(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         1936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1514
_refine_ls_R_factor_gt           0.0847
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1386P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2281
_refine_ls_wR_factor_ref         0.2535
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1070
_reflns_number_total             1936
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00900_si_002.cif
_cod_data_source_block           compound_5e
_cod_original_cell_volume        1554.9(11)
_cod_database_code               4035837
_shelxl_version_number           2014-1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              78823
_shelx_hkl_checksum              87410
_olex2_submission_special_instructions 'No special instructions were received'