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_4035840
_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         'C22 H14 F3 N O4'
_chemical_formula_sum            'C22 H14 F3 N O4'
_chemical_formula_weight         413.34
_chemical_name_systematic        svk_591
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-05
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                95.328(4)
_cell_angle_beta                 91.807(3)
_cell_angle_gamma                102.699(4)
_cell_formula_units_Z            2
_cell_length_a                   7.1559(3)
_cell_length_b                   9.9916(6)
_cell_length_c                   13.0540(4)
_cell_measurement_reflns_used    3846
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.4440
_cell_measurement_theta_min      2.9190
_cell_volume                     905.28(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0419
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -46.00   23.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6208  -77.0000  -30.0000 69

  2 omega  -21.00   64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6208  -98.0000  -97.0000 85

  3 omega    9.00   54.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6208   37.0000 -120.0000 45

  4 omega   -7.00   93.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6208   77.0000   30.0000 100

  5 omega  -84.00   12.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.3240  -77.0000   90.0000 96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0295166000
_diffrn_orient_matrix_UB_12      -0.0579722000
_diffrn_orient_matrix_UB_13      -0.0371694000
_diffrn_orient_matrix_UB_21      0.0248382000
_diffrn_orient_matrix_UB_22      -0.0432570000
_diffrn_orient_matrix_UB_23      0.0358202000
_diffrn_orient_matrix_UB_31      -0.0941558000
_diffrn_orient_matrix_UB_32      -0.0109325000
_diffrn_orient_matrix_UB_33      0.0179426000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6146
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.49
_diffrn_source                   'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.890
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0042(16)
_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   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.6248P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1241
_reflns_number_gt                2684
_reflns_number_total             3186
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b00900_si_002.cif
_cod_data_source_block           compound_6j
_cod_original_cell_volume        905.29(7)
_cod_database_code               4035840
_chemical_oxdiff_formula         'C15 H17 O6 N1'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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:
 C12(H12), C13(H13), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21),
 C22(H22), C26(H26), C27(H27), C28(H28)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_olex2_submission_original_sample_id svk_591
_olex2_submission_special_instructions 'No special instructions were received'