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_4035839
_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
_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     direct
_audit_creation_date             2016-06-23
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.419(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.547(2)
_cell_length_b                   4.2555(2)
_cell_length_c                   30.3660(19)
_cell_measurement_reflns_used    2835
_cell_measurement_temperature    298
_cell_measurement_theta_max      20.727
_cell_measurement_theta_min      2.394
_cell_volume                     3829.6(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1623
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            31871
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.378
_diffrn_reflns_theta_max         25.378
_diffrn_reflns_theta_min         2.395
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0765 before and 0.0577 after correction.
The Ratio of minimum to maximum transmission is 0.8449.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       needle
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1771
_refine_ls_R_factor_gt           0.0775
_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^)+(0.0559P)^2^+4.7271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1900
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1630
_reflns_number_total             3498
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00900_si_002.cif
_cod_data_source_block           compound_5j
_cod_original_cell_volume        3829.5(4)
_cod_database_code               4035839
_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. Others
 Fixed Sof: F1AA(0.5) F2(0.5) F2AA(0.5) F1(0.5) F0AA(0.5) F3(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00I),
 C00K(H00K), C00L(H00L), C00M(H00M), C00R(H00R), C00V(H00V)
3.b Idealised Me refined as rotating group:
 C00U(H00A,H00D,H00H)
;
_shelx_res_checksum              93275
_shelx_hkl_checksum              26893
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'