PIDA mediated oxidative annulation of aryl methyl ketones: a facile approach for the chemoselective synthesis of 5-substituted oxazoles.
Devaraju, Mohankumar; Prasad Dasappa, Jagadeesh; Organic & biomolecular chemistry 23 (2025) 2891–2895; doi:10.1039/d4ob01427h

data_7160380
_publ_section_title
;
 PIDA mediated oxidative annulation of aryl methyl ketones: a facile
 approach for the chemoselective synthesis of 5-substituted oxazoles.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2891
_journal_page_last               2895
_journal_paper_doi               10.1039/d4ob01427h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C10 H9 N O3 S'
_chemical_formula_sum            'C11 H10 Cl N O2 S0'
_chemical_formula_weight         223.65
_chemical_name_systematic        5-(4-(methylsulfonyl)phenyl)thiazole
_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     iterative
_audit_creation_date             2023-08-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-05-08 deposited with the CCDC.	2025-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 129.1550(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.6755(9)
_cell_length_b                   7.0600(3)
_cell_length_c                   16.2241(7)
_cell_measurement_reflns_used    9868
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      3.11
_cell_volume                     2014.05(15)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32079
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.560
_diffrn_reflns_theta_min         2.525
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.7842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0560 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.9095.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         3075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.209
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0550
_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^)+(0.0649P)^2^+2.6852P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1476
_refine_ls_wR_factor_ref         0.1648
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2657
_reflns_number_total             3075
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01427h2.cif
_cod_data_source_block           ag11
_cod_depositor_comments
'Adding full bibliography for 7160379--7160380.cif.'
_cod_database_code               7160380
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.895
_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), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_olex2_submission_special_instructions 'No special instructions were received'