Hypervalent iodane mediated reactions of N-acetyl enamines for the synthesis of oxazoles and imidazoles.
Xu, Kang; Yang, Ruiqi; Yang, Shuang; Jiang, Cheng; Ding, Zhenhua; Organic & biomolecular chemistry 17 (2019) 8977–8981; doi:10.1039/c9ob01895f

data_7157113
_publ_section_title
;
 Hypervalent iodane mediated reactions of N-acetyl enamines for the
 synthesis of oxazoles and imidazoles.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8977
_journal_page_last               8981
_journal_paper_doi               10.1039/c9ob01895f
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C10 H8 Br N O'
_chemical_formula_sum            'C10 H8 Br N O'
_chemical_formula_weight         238.08
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-05 deposited with the CCDC.    2019-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                81.991(5)
_cell_angle_beta                 89.552(5)
_cell_angle_gamma                82.145(5)
_cell_formula_units_Z            4
_cell_length_a                   5.6468(5)
_cell_length_b                   12.0159(10)
_cell_length_c                   14.1013(13)
_cell_measurement_reflns_used    4539
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      2.41
_cell_volume                     938.51(14)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      149.99
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0474
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12592
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         2.412
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.335
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0951 before and 0.0518 after correction. The Ratio of minimum to maximum transmission is 0.5828. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.870
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.182
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0631
_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^)+(0.0064P)^2^+10.4222P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1577
_refine_ls_wR_factor_ref         0.1658
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2849
_reflns_number_total             3641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01895f2.cif
_cod_data_source_block           mo_1211_3_0m
_cod_depositor_comments
'Adding full bibliography for 7157113--7157114.cif.'
_cod_database_code               7157113
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.723
_shelx_estimated_absorpt_t_min   0.493
_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:
 C3(H3), C5(H5), C2(H2), C17(H17), C6(H6), C19(H19), C8(H8), C16(H16),
 C20(H20), C13(H13)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'