Synthesis of Isoxazole- and Oxazole-4-carboxylic Acids Derivatives by Controlled Isoxazole-Azirine-Isoxazole/Oxazole Isomerization.
Serebryannikova, Anna V.; Galenko, Ekaterina E.; Novikov, Mikhail Sergeevich; Khlebnikov, Alexander F.; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02536

data_4034704
_publ_section_title
;
 Synthesis of Isoxazole- and Oxazole-4-carboxylic Acids Derivatives by
 Controlled Isoxazole-Azirine-Isoxazole/Oxazole Isomerization.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02536
_journal_year                    2019
_chemical_formula_moiety         'C11 H8 F N O3'
_chemical_formula_sum            'C11 H8 F N O3'
_chemical_formula_weight         221.18
_chemical_name_systematic
'methyl 2-(4-fluorophenyl)oxazole-4-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.102(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.1591(6)
_cell_length_b                   5.7258(2)
_cell_length_c                   7.1647(2)
_cell_measurement_reflns_used    4690
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.9960
_cell_measurement_theta_min      5.7410
_cell_volume                     947.64(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -42.00 -15.00   1.00    1.00    --  -40.13 -38.00 -30.00   27
  2  \w   -112.00 -68.00   1.00    1.00    --  -40.13 -38.00 -30.00   44
  3  \w   -104.00 -59.00   1.00    1.00    --  -40.13 178.00-180.00   45
  4  \w     60.00 123.00   1.00    1.00    --   40.13 178.00 -90.00   63
  5  \w    114.00 174.00   1.00    1.00    --  113.00 112.00 -60.00   60
  6  \w    119.00 151.00   1.00    1.00    --  113.00  61.00  30.00   32
  7  \w    109.00 176.00   1.00    1.00    --  113.00  77.00 120.00   67
  8  \w    107.00 133.00   1.00    1.00    --  113.00 -61.00  30.00   26
  9  \w     57.00 108.00   1.00    1.00    --  113.00 -95.00 -30.00   51
 10  \w     42.00  84.00   1.00    1.00    --  113.00 -61.00  30.00   42
 11  \w     30.00 109.00   1.00    1.00    --  113.00 -95.00 120.00   79
 12  \w     37.00 130.00   1.00    1.00    --  113.00 -30.00-180.00   93
 13  \w     50.00  87.00   1.00    1.00    --  113.00 -61.00-180.00   37
 14  \w     58.00 127.00   1.00    1.00    --   40.13 178.00  90.00   69
 15  \w    -49.00 -14.00   1.00    1.00    --  -40.13 -38.00   0.00   35
 16  \w   -101.00 -12.00   1.00    1.00    --  -40.13 -77.00 150.00   89
 17  \w     58.00  86.00   1.00    1.00    --   40.13 178.00-150.00   28
 18  \w     94.00 121.00   1.00    1.00    --   40.13 178.00-150.00   27
 19  \w    -35.00  15.00   1.00    1.00    --   40.13 -38.00-120.00   50
 20  \w     85.00 149.00   1.00    1.00    --  113.00  45.00  90.00   64
 21  \w     92.00 119.00   1.00    1.00    --  113.00  61.00  30.00   27
 22  \w     86.00 147.00   1.00    1.00    --  113.00  45.00   0.00   61
 23  \w     86.00 113.00   1.00    1.00    --  113.00  30.00  90.00   27
 24  \w     85.00 111.00   1.00    1.00    --  113.00  45.00 -90.00   26
 25  \w     80.00 106.00   1.00    1.00    --  113.00  77.00   0.00   26
 26  \w     53.00  79.00   1.00    1.00    --  113.00 -30.00  90.00   26
 27  \w     90.00 129.00   1.00    1.00    --  113.00 -30.00  90.00   39
 28  \w     86.00 112.00   1.00    1.00    --  113.00  45.00  60.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0599973000
_diffrn_orient_matrix_UB_12      -0.1168168000
_diffrn_orient_matrix_UB_13      0.0248423000
_diffrn_orient_matrix_UB_21      -0.0216044000
_diffrn_orient_matrix_UB_22      -0.1573928000
_diffrn_orient_matrix_UB_23      0.1548810000
_diffrn_orient_matrix_UB_31      -0.0195186000
_diffrn_orient_matrix_UB_32      -0.1843621000
_diffrn_orient_matrix_UB_33      -0.1478526000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6035
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.470
_diffrn_reflns_theta_min         3.827
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_preparation       'Slow evaporation of DCM/hexane'
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0546P)^2^+0.5739P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1037
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1793
_reflns_number_total             1871
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02536_si_002.cif
_cod_data_source_block           10681-13598
_cod_database_code               4034704
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 F N O3'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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:
 C9(H9), C5(H5), C1(H1), C8(H8), C6(H6)
2.b Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c)
;
_shelx_res_checksum              600
_shelx_hkl_checksum              21697
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.666
_oxdiff_exptl_absorpt_empirical_full_min 0.623