Synthesis of 4-amino-5-allenylisoxazoles <i>via</i> gold(I)-catalysed propargyl aza-Claisen rearrangement.
Tsuda, Masato; Morita, Taiki; Fukuhara, Shintaro; Nakamura, Hiroyuki; Organic & biomolecular chemistry 19 (2021) 1358–1364; doi:10.1039/d0ob02544e

data_7157845
_publ_section_title
;
 Synthesis of 4-amino-5-allenylisoxazoles <i>via</i> gold(I)-catalysed
 propargyl aza-Claisen rearrangement.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1358
_journal_page_last               1364
_journal_paper_doi               10.1039/d0ob02544e
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C23 H26 N2 O3 S Si'
_chemical_formula_sum            'C23 H26 N2 O3 S Si'
_chemical_formula_weight         438.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-17
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2020-09-04 deposited with the CCDC.	2021-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                112.371(2)
_cell_angle_beta                 101.901(2)
_cell_angle_gamma                101.004(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1798(2)
_cell_length_b                   10.3113(2)
_cell_length_c                   12.4879(3)
_cell_measurement_reflns_used    16377
_cell_measurement_temperature    90
_cell_measurement_theta_max      76.4560
_cell_measurement_theta_min      3.9870
_cell_volume                     1132.33(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_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      90
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.958
_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     29.00  88.00   0.50    0.09    --   46.45  65.00 -79.00  118
  2  \w     86.00 175.00   0.50    0.34    --  104.75  77.00-150.00  178
  3  \w    138.00 164.00   0.50    0.34    --  104.75  45.00-120.00   52
  4  \w     87.00 168.00   0.50    0.34    --  104.75  65.00 -79.00  162
  5  \w     70.00 103.00   0.50    0.34    --  104.75 -94.00 150.00   66
  6  \w     80.00 111.00   0.50    0.34    --  104.75-125.00  30.00   62
  7  \w     36.00 105.00   0.50    0.34    --  104.75 -94.00   0.00  138
  8  \w     33.00  61.00   0.50    0.34    --  104.75-125.00-180.00   56
  9  \w     64.00 110.00   0.50    0.34    --  104.75-125.00-180.00   92
 10  \w     78.00 106.00   0.50    0.34    --  104.75 -94.00 -90.00   56
 11  \w     47.00  74.00   0.50    0.34    --  104.75 -94.00 -90.00   54
 12  \w     33.00  58.00   0.50    0.34    --  104.75 -77.00  30.00   50
 13  \w     33.00  80.00   0.50    0.34    --  104.75 -65.00 144.00   94
 14  \w    -15.00  62.00   0.50    0.09    --   46.45 -65.00 144.00  154
 15  \w     68.00 106.00   0.50    0.34    --  104.75 -77.00  30.00   76
 16  \w     32.00  64.00   0.50    0.34    --  104.75 -61.00 -60.00   64
 17  \w     38.00 106.00   0.50    0.34    --  104.75 -77.00-150.00  136
 18  \w    -18.00   9.00   0.50    0.09    --   46.45 -19.00-150.00   54
 19  \w    -20.00  21.00   0.50    0.09    --  -46.45  19.00  60.00   82
 20  \w    -19.00  18.00   0.50    0.09    --  -46.45  37.00  30.00   74
 21  \w    -18.00  24.00   0.50    0.09    --  -46.45  65.00 -79.00   84
 22  \w    -47.00 -21.00   0.50    0.09    --  -46.45  65.00 -79.00   52
 23  \w    -21.00  29.00   0.50    0.09    --  -46.45  19.00 -90.00  100
 24  \w    -23.00  10.00   0.50    0.09    --  -46.45  19.00-150.00   66
 25  \w    -76.00 -29.00   0.50    0.34    -- -102.00  65.00 -79.00   94
 26  \w    -66.00 -35.00   0.50    0.34    -- -102.00  61.00   0.00   62
 27  \w    -67.00 -30.00   0.50    0.34    -- -102.00  61.00  90.00   74
 28  \w    -56.00 -31.00   0.50    0.34    -- -102.00  61.00 120.00   50
 29  \w   -112.00 -56.00   0.50    0.34    -- -102.00 125.00  60.00  112
 30  \w   -110.00 -77.00   0.50    0.34    -- -102.00 125.00-150.00   66
 31  \w   -174.00 -85.00   0.50    0.34    -- -102.00 -61.00-150.00  178
 32  \w   -173.00-115.00   0.50    0.34    -- -102.00 -30.00-180.00  116
 33  \w   -154.00 -92.00   0.50    0.34    -- -102.00 -45.00  30.00  124
 34  \w   -111.00 -40.00   0.50    0.09    --  -46.45 -65.00 144.00  142
 35  \w   -173.00 -90.00   0.50    0.34    -- -102.00 -65.00 144.00  166
 36  \w   -114.00 -87.00   0.50    0.34    -- -102.00-125.00 -90.00   54
 37  \w   -160.00-134.00   0.50    0.34    -- -102.00-125.00 -90.00   52
 38  \w     32.00  57.00   0.50    0.34    --  104.75 -65.00 144.00   50
 39  \w   -116.00 -89.00   0.50    0.09    --  -46.45 -42.00 -25.77   54
 40  \w    -55.00 -28.00   0.50    0.09    --  -46.45 -65.00 144.00   54
 41  \w    -94.00 -18.00   0.50    0.09    --  -46.45 125.00  60.00  152
 42  \w    -77.00 -35.00   0.50    0.09    --  -46.45 -19.00   0.00   84
 43  \w    -66.00 -34.00   0.50    0.09    --  -46.45 -42.00 -25.77   64
 44  \w     32.00  62.00   0.50    0.09    --   46.45  57.00-120.00   60
 45  \w     88.00 118.00   0.50    0.09    --   46.45  77.00 -30.00   60
 46  \w     24.00  53.00   0.50    0.09    --   46.45  77.00  90.00   58
 47  \w     30.00  56.00   0.50    0.09    --   46.45  77.00 120.00   52
 48  \w     35.00  62.00   0.50    0.09    --   46.45  37.00-180.00   54
 49  \w     24.00  79.00   0.50    0.09    --   46.45  77.00 -30.00  110
 50  \w     30.00  65.00   0.50    0.09    --   46.45  77.00-150.00   70
 51  \w     25.00  58.00   0.50    0.09    --   46.45  77.00 150.00   66
 52  \w     37.00  64.00   0.50    0.09    --   46.45  37.00 120.00   54
 53  \w     66.00 100.00   0.50    0.09    --   46.45  57.00-120.00   68
 54  \w     24.00  61.00   0.50    0.09    --   46.45  77.00  30.00   74
 55  \w     45.00  93.00   0.50    0.09    --   46.45  37.00-150.00   96
 56  \w     88.00 118.00   0.50    0.09    --   46.45  37.00 120.00   60
 57  \w     34.00  59.00   0.50    0.09    --   46.45  57.00   0.00   50
 58  \w     64.00 114.00   0.50    0.09    --   46.45  77.00 -90.00  100
 59  \w     24.00  50.00   0.50    0.09    --   46.45  77.00 -90.00   52
 60  \w   -173.00-118.00   0.50    0.34    -- -102.00 -80.00  79.18  110
 61  \w   -112.00 -80.00   0.50    0.34    -- -102.00 -74.00 -30.10   64
 62  \w   -107.00 -80.00   0.50    0.34    -- -102.00 -75.00 170.27   54
 63  \w   -173.00-147.00   0.50    0.34    -- -102.00 -75.00  50.02   52
 64  \w   -172.00-146.00   0.50    0.34    -- -102.00 -74.00 -30.10   52
 65  \w   -110.00 -80.00   0.50    0.34    -- -102.00 -75.00  50.02   60
 66  \w   -126.00 -85.00   0.50    0.34    -- -102.00 -61.00 -60.00   82
 67  \w   -114.00 -87.00   0.50    0.34    -- -102.00 -55.00-170.36   54
 68  \w   -157.00-130.00   0.50    0.34    -- -102.00 -77.00-120.00   54
 69  \w   -169.00-132.00   0.50    0.34    -- -102.00 -75.00 170.27   74
 70  \w   -166.00-118.00   0.50    0.34    -- -102.00 -51.00  85.01   96
 71  \w   -114.00 -84.00   0.50    0.34    -- -102.00 -65.00  24.99   60
 72  \w   -160.00-117.00   0.50    0.34    -- -102.00 -65.00  24.99   86
 73  \w   -113.00 -86.00   0.50    0.34    -- -102.00 -59.00 170.90   54
 74  \w   -105.00 -79.00   0.50    0.34    -- -102.00 -77.00 -60.00   52
 75  \w   -107.00 -80.00   0.50    0.34    -- -102.00 -75.00 141.56   54
 76  \w   -105.00 -78.00   0.50    0.34    -- -102.00 -80.00  13.80   54
 77  \w   -141.00-115.00   0.50    0.34    -- -102.00 -80.00  13.80   52
 78  \w   -111.00 -83.00   0.50    0.34    -- -102.00 -72.00 128.45   56
 79  \w   -108.00 -82.00   0.50    0.34    -- -102.00 -71.00 -90.49   52
 80  \w   -161.00-117.00   0.50    0.34    -- -102.00 -72.00 128.45   88
 81  \w   -141.00 -85.00   0.50    0.34    -- -102.00 -61.00 -30.00  112
 82  \w    -58.00 -31.00   0.50    0.34    -- -102.00  61.00-120.00   54
 83  \w   -107.00 -80.00   0.50    0.34    -- -102.00 -76.00  22.36   54
 84  \w   -111.00 -85.00   0.50    0.34    -- -102.00 -61.00-120.00   52
 85  \w   -112.00 -85.00   0.50    0.34    -- -102.00 -61.00-180.00   54
 86  \w   -110.00 -84.00   0.50    0.34    -- -102.00 -68.00 114.48   52
 87  \w   -109.00 -78.00   0.50    0.34    -- -102.00 -79.00 -70.12   62
 88  \w   -155.00-128.00   0.50    0.34    -- -102.00 -79.00 -70.12   54
 89  \w   -113.00 -88.00   0.50    0.34    -- -102.00 -51.00  85.01   50
 90  \w   -105.00 -79.00   0.50    0.34    -- -102.00 -77.00-180.00   52
 91  \w   -174.00-147.00   0.50    0.34    -- -102.00 -77.00   0.00   54
 92  \w   -122.00 -79.00   0.50    0.34    -- -102.00 -77.00   0.00   86
 93  \w   -106.00 -79.00   0.50    0.34    -- -102.00 -77.00  60.00   54
 94  \w   -104.00 -78.00   0.50    0.34    -- -102.00 -79.00  35.99   52
 95  \w   -175.00-149.00   0.50    0.34    -- -102.00 -61.00-180.00   52
 96  \w   -140.00 -90.00   0.50    0.34    -- -102.00 -51.00  54.62  100
 97  \w   -104.00 -78.00   0.50    0.34    -- -102.00 -79.00-129.09   52
 98  \w   -113.00 -87.00   0.50    0.34    -- -102.00 -57.00-177.77   52
 99  \w   -113.00 -86.00   0.50    0.34    -- -102.00 -61.00  90.00   54
100  \w   -106.00 -79.00   0.50    0.34    -- -102.00 -76.00 155.84   54
101  \w   -156.00-131.00   0.50    0.34    -- -102.00 -79.00-129.09   50
102  \w   -105.00 -79.00   0.50    0.34    -- -102.00 -77.00-120.00   52
103  \w   -103.00 -78.00   0.50    0.34    -- -102.00 -80.00  79.18   50
104  \w   -143.00-117.00   0.50    0.34    -- -102.00 -68.00 114.48   52
105  \w   -107.00 -81.00   0.50    0.34    -- -102.00 -77.00  90.00   52
106  \w     88.00 113.00   0.50    0.34    --  104.75  65.00  93.29   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0834793000
_diffrn_orient_matrix_UB_12      0.0565613000
_diffrn_orient_matrix_UB_13      0.0886399000
_diffrn_orient_matrix_UB_21      0.0330597000
_diffrn_orient_matrix_UB_22      -0.1039090000
_diffrn_orient_matrix_UB_23      0.0564648000
_diffrn_orient_matrix_UB_31      0.1348471000
_diffrn_orient_matrix_UB_32      0.1210168000
_diffrn_orient_matrix_UB_33      0.0927715000
_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  0.0402
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30216
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.528
_diffrn_reflns_theta_min         4.023
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.993
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.146
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.109
_refine_diff_density_max         0.906
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0624P)^2^+0.7047P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4169
_reflns_number_total             4555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02544e2.cif
_cod_data_source_block           tsuda1
_cod_depositor_comments          'Adding full bibliography for 7157845.cif.'
_cod_database_code               7157845
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.812
_shelx_estimated_absorpt_t_min   0.760
_diffrn_oxdiff_digest_frames
;
015bf584c7d866277c684d377a7df9357400075089b
;
_diffrn_oxdiff_digest_hkl
;
01a1b1b71b2c820cf44551e8db2af199c68921
;
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C17(H17), C5(H5), C15(H15), C3(H3), C16(H16), C13(H13),
 C25(H25), C14(H14)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C11(H11A,H11B,H11C), C30(H30A,H30B,
 H30C), C26(H26A,H26B,H26C)
;
_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 1.389
_oxdiff_exptl_absorpt_empirical_full_min 0.783