Hypervalent iodine-promoted twofold oxidative coupling of amines with amides and thioamides: chemoselective pathway to oxazoles and thiazoles.
Nan, Jiang; Ren, Xin; Yan, Qiang; Liu, Shilei; Wang, Jing; Ma, Yangmin; Szostak, Michal; Chemical science 14 (2023) 3338–3345; doi:10.1039/d3sc00301a

data_1568539
_publ_section_title
;
 Hypervalent iodine-promoted twofold oxidative coupling of amines with
 amides and thioamides: chemoselective pathway to oxazoles and thiazoles.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              3338
_journal_page_last               3345
_journal_paper_doi               10.1039/d3sc00301a
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C12 H9 N S'
_chemical_formula_sum            'C12 H9 N S'
_chemical_formula_weight         199.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2dnkbz
_audit_creation_date             2022-12-03
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2022-12-05 deposited with the CCDC.	2023-02-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.817(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.5785(6)
_cell_length_b                   19.2356(16)
_cell_length_c                   13.4588(11)
_cell_measurement_reflns_used    9444
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.596
_cell_measurement_theta_min      2.604
_cell_volume                     1959.6(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            49798
_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         2.604
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0795 before and 0.0684 after correction.
The Ratio of minimum to maximum transmission is 0.8784.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0731
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0273P)^2^+3.8582P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1686
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2321
_reflns_number_total             3431
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00301a2.cif
_cod_data_source_block           sust_3454_0m
_cod_depositor_comments
;
Adding full bibliography for 1568538--1568539.cif.

2025-05-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C24 H18 N2 S2'
_cod_original_formula_weight         398.52
_cod_original_formula_moiety         '2(C12 H9 N S)'
_cod_original_formula_units_Z            4
_cod_database_code               1568539
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.945
_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), C16(H16), C17(H17), C18(H18), C21(H21), C9(H9), C12(H12),
 C13(H13), C15(H15), C20(H20), C22(H22)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              37060
_shelx_hkl_checksum              24067
_olex2_submission_special_instructions 'No special instructions were received'