Regioselective Synthesis of 5-Aminooxazoles via Cp*Co(III)-Catalyzed Formal [3 + 2] Cycloaddition of N-(Pivaloyloxy)amides with Ynamides.
Han, Xiang-Lei; Zhou, Chu-Jun; Liu, Xu-Ge; Zhang, Shang-Shi; Wang, Honggen; Li, Qingjiang; Organic letters 19 (2017) 6108–6111; doi:10.1021/acs.orglett.7b02959

data_1556076
_publ_section_title
;
 Regioselective Synthesis of 5-Aminooxazoles via Cp*Co(III)-Catalyzed
 Formal [3 + 2] Cycloaddition of N-(Pivaloyloxy)amides with Ynamides.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              6108
_journal_page_last               6111
_journal_paper_doi               10.1021/acs.orglett.7b02959
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C17 H16 N2 O3 S'
_chemical_formula_sum            'C17 H16 N2 O3 S'
_chemical_formula_weight         328.39
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.8838(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.58500(19)
_cell_length_b                   9.10460(16)
_cell_length_c                   16.2981(3)
_cell_measurement_reflns_used    4909
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.9740
_cell_measurement_theta_min      2.6830
_cell_volume                     1567.08(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.9979
_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    -23.00  18.00   1.00    3.00    --  -44.52  57.00  90.00   41
  2  \w    -66.00 -26.00   1.00    3.00    --  -44.52  57.00  90.00   40
  3  \w    -70.00  19.00   1.00    3.00    --  -44.52  57.00-150.00   89
  4  \w   -118.00 -88.00   1.00    3.00    --  -44.52-125.00-120.00   30
  5  \w   -159.00-127.00   1.00   10.00    --  -90.00 -45.00-180.00   32
  6  \w     29.00  66.00   1.00   10.00    --  100.00 -30.00 -90.00   37
  7  \w     83.00 127.00   1.00   10.00    --  100.00 -30.00 -90.00   44
  8  \w     85.00 151.00   1.00   10.00    --  100.00  30.00-150.00   66
  9  \w     73.00 173.00   1.00   10.00    --  100.00  30.00 -90.00  100
 10  \w     39.00 102.00   1.00   10.00    --  100.00 -30.00   0.00   63
 11  \w     34.00 126.00   1.00   10.00    --  100.00 -61.00 -30.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0585559000
_diffrn_orient_matrix_UB_12      -0.1157649000
_diffrn_orient_matrix_UB_13      -0.0602066000
_diffrn_orient_matrix_UB_21      -0.0387392000
_diffrn_orient_matrix_UB_22      -0.0930363000
_diffrn_orient_matrix_UB_23      0.0731437000
_diffrn_orient_matrix_UB_31      -0.1278874000
_diffrn_orient_matrix_UB_32      0.0809915000
_diffrn_orient_matrix_UB_33      -0.0019195000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6743
_diffrn_reflns_theta_full        67.0773
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         5.15
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.983
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3918
_exptl_crystal_description       block
_exptl_crystal_F_000             691.4364
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.3462
_refine_diff_density_min         -0.4656
_refine_diff_density_rms         0.0606
_refine_ls_d_res_high            0.8370
_refine_ls_d_res_low             8.5948
_refine_ls_goodness_of_fit_ref   1.0508
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0508
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.4709P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0864
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -12
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -9
_reflns_number_gt                2579
_reflns_number_total             2796
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ol7b02959_si_002.cif
_cod_data_source_block           hxl_170427
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               1556076
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C15(H15), C12(H12), C17(H17), C20(H20), C10(H10), C18(H18), C22(H22),
 C21(H21), C19(H19), C14(H14)
2.b Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C9(H9a,H9b,H9c)
;
_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 2.113
_oxdiff_exptl_absorpt_empirical_full_min 0.556