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_1556077
_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         'C15 H14 N2 O4 S'
_chemical_formula_sum            'C15 H14 N2 O4 S'
_chemical_formula_weight         318.36
_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             2017-05-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.0940(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.36180(12)
_cell_length_b                   9.18131(13)
_cell_length_c                   15.6457(2)
_cell_measurement_reflns_used    5866
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.3450
_cell_measurement_theta_min      4.2520
_cell_volume                     1488.45(3)
_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 0.9902
_diffrn_measured_fraction_theta_max 0.9902
_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     62.00 116.00   1.00    2.00    --   44.52  37.00 -60.00   54
  2  \w     80.00 168.00   1.00    3.00    --  100.00  45.00  30.00   88
  3  \w     79.00 105.00   1.00    3.00    --  100.00 -94.00-120.00   26
  4  \w     39.00  74.00   1.00    3.00    --  100.00 -94.00-120.00   35
  5  \w     30.00 118.00   1.00    3.00    --  100.00-125.00-150.00   88
  6  \w      1.00  70.00   1.00    2.00    --   44.52 -57.00-180.00   69
  7  \w   -161.00-119.00   1.00    3.00    --  -90.00 -30.00   0.00   42
  8  \w   -118.00 -82.00   1.00    2.00    --  -44.40-125.00  30.00   36
  9  \w   -103.00 -77.00   1.00    3.00    --  -90.00 -30.00 150.00   26
 10  \w   -110.00 -84.00   1.00    3.00    --  -90.00 125.00  30.00   26
 11  \w   -163.00-129.00   1.00    3.00    --  -90.00 -30.00 150.00   34
 12  \w     93.00 124.00   1.00    3.00    --  100.00 -45.00 150.00   31
 13  \w     51.00  77.00   1.00    3.00    --  100.00-111.00 -81.00   26
 14  \w     30.00  77.00   1.00    3.00    --  100.00 -45.00 150.00   47
 15  \w     36.00 102.00   1.00    3.00    --  100.00-125.00  30.00   66
;
_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      -0.0194893000
_diffrn_orient_matrix_UB_12      -0.0964560000
_diffrn_orient_matrix_UB_13      -0.0796316000
_diffrn_orient_matrix_UB_21      0.0236915000
_diffrn_orient_matrix_UB_22      -0.1370285000
_diffrn_orient_matrix_UB_23      0.0546773000
_diffrn_orient_matrix_UB_31      -0.1453514000
_diffrn_orient_matrix_UB_32      -0.0093293000
_diffrn_orient_matrix_UB_33      0.0193990000
_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  0.0194
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7127
_diffrn_reflns_theta_full        67.0689
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         5.66
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61961
_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    1.4205
_exptl_crystal_description       block
_exptl_crystal_F_000             667.4973
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.3554
_refine_diff_density_min         -0.3890
_refine_diff_density_rms         0.0495
_refine_ls_d_res_high            0.8371
_refine_ls_d_res_low             7.8228
_refine_ls_goodness_of_fit_ref   1.0451
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0451
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+0.8011P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0896
_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              18
_reflns_limit_l_min              -9
_reflns_number_gt                2503
_reflns_number_total             2628
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ol7b02959_si_003.cif
_cod_data_source_block           hxl_170504
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               1556077
_reflns_odcompleteness_completeness 99.01
_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:
 C14(H14), C17(H17), C18(H18), C20(H20), C12(H12), C16(H16), C19(H19), C21(H21)
2.b Idealised Me refined as rotating group:
 C9(H9c,H9b,H9a), C10(H10a,H10b,H10c)
;
_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 1.573
_oxdiff_exptl_absorpt_empirical_full_min 0.644