Rhodium- and Non-Metal-Catalyzed Approaches for the Conversion of Isoxazol-5-ones to 2,3-Dihydro-6H-1,3-oxazin-6-ones.
Jurberg, Igor D.; Davies, Huw M. L.; Organic letters 19 (2017) 5158–5161; doi:10.1021/acs.orglett.7b02436

data_1547133
_publ_section_title
;
 Rhodium- and Non-Metal-Catalyzed Approaches for the Conversion of
 Isoxazol-5-ones to 2,3-Dihydro-6H-1,3-oxazin-6-ones.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5158
_journal_page_last               5161
_journal_paper_doi               10.1021/acs.orglett.7b02436
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C17 H20 Br N O4'
_chemical_formula_sum            'C17 H20 Br N O4'
_chemical_formula_weight         382.25
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-03
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5332)
;
_cell_angle_alpha                100.937(3)
_cell_angle_beta                 101.585(4)
_cell_angle_gamma                103.902(4)
_cell_formula_units_Z            2
_cell_length_a                   6.3863(3)
_cell_length_b                   12.2125(6)
_cell_length_c                   12.3641(3)
_cell_measurement_reflns_used    11877
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      77.4100
_cell_measurement_theta_min      3.6930
_cell_volume                     887.81(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 HyPix
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_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 -32.00   0.50    0.50    --  -15.25 -57.00  30.00   60
  2  \w    -28.00  -1.00   0.50    0.50    --  -15.25 -57.00  30.00   54
  3  \w     18.00  48.00   0.50    0.50    --   15.25 -98.00 -14.00   60
  4  \w     13.00  50.00   0.50    0.50    --   15.25 -99.00 -90.00   74
  5  \w     24.00  50.00   0.50    0.50    --   15.25 -99.00  60.00   52
  6  \w     43.00 109.00   0.50    2.00    --  110.00 -98.00 -14.00  132
  7  \w     89.00 116.00   0.50    2.00    --  110.00-125.00  90.00   54
  8  \w     39.00 134.00   0.50    2.00    --  110.00 -77.00  60.00  190
  9  \w     61.00  87.00   0.50    0.50    --   15.25  57.00 -30.00   52
 10  \w     22.00  63.00   0.50    0.50    --   15.25  38.00-150.00   82
 11  \w     -1.00  60.00   0.50    0.50    --   15.25  77.00-120.00  122
 12  \w      2.00  35.00   0.50    0.50    --   15.25  57.00 -30.00   66
 13  \w     -3.00  27.00   0.50    0.50    --   15.25  98.00  92.00   60
 14  \w    -49.00  -1.00   0.50    0.50    --  -15.25  98.00  92.00   96
 15  \w    -43.00  -1.00   0.50    0.50    --  -15.25 -38.00  60.00   84
 16  \w    -80.00 -54.00   0.50    0.50    --  -15.25 -38.00  60.00   52
 17  \w    -88.00 -22.00   0.50    0.50    --  -15.25 -38.00 150.00  132
 18  \w    -97.00 -65.00   0.50    2.00    --  -88.50 -77.00   0.00   64
 19  \w    -95.00 -65.00   0.50    2.00    --  -88.50 -77.00  60.00   60
 20  \w    -93.00 -65.00   0.50    2.00    --  -88.50 -77.00  90.00   56
 21  \w    -92.00 -65.00   0.50    2.00    --  -88.50 -77.00 150.00   54
 22  \w   -101.00 -66.00   0.50    2.00    --  -88.50 -77.00 120.00   70
 23  \w   -110.00 -72.00   0.50    2.00    --  -88.50 -51.00 102.34   76
 24  \w   -101.00 -74.00   0.50    2.00    --  -88.50 -57.00 120.00   54
 25  \w   -116.00 -72.00   0.50    2.00    --  -88.50 -57.00 150.00   88
 26  \w   -111.00 -77.00   0.50    2.00    --  -88.50 -38.00  60.00   68
 27  \w   -102.00 -65.00   0.50    2.00    --  -88.50 -77.00  30.00   74
 28  \w   -107.00 -79.00   0.50    2.00    --  -88.50 -38.00  30.00   56
 29  \w   -106.00 -75.00   0.50    2.00    --  -88.50 -57.00  30.00   62
 30  \w   -105.00 -73.00   0.50    2.00    --  -88.50 -46.00 -54.41   64
 31  \w    -91.00 -65.00   0.50    2.00    --  -88.50 -76.00 -81.11   52
 32  \w    -91.00 -65.00   0.50    2.00    --  -88.50 -77.00-120.00   52
 33  \w    -90.00 -65.00   0.50    2.00    --  -88.50 -77.00-180.00   50
 34  \w    -98.00 -65.00   0.50    2.00    --  -88.50 -77.00-150.00   66
 35  \w   -106.00 -72.00   0.50    2.00    --  -88.50 -58.00-157.78   68
 36  \w   -107.00 -72.00   0.50    2.00    --  -88.50 -54.00-138.46   70
 37  \w   -102.00 -65.00   0.50    2.00    --  -88.50 -77.00 -90.00   74
 38  \w    -89.00 -64.00   0.50    2.00    --  -88.50 -78.00 -54.80   50
 39  \w   -100.00 -74.00   0.50    2.00    --  -88.50 -57.00 -90.00   52
 40  \w   -113.00 -73.00   0.50    2.00    --  -88.50 -37.00-148.35   80
 41  \w   -128.00 -74.00   0.50    2.00    --  -88.50 -57.00-180.00  108
 42  \w   -145.00-120.00   0.50    2.00    --  -88.50 -98.00 -14.00   50
 43  \w   -136.00 -72.00   0.50    2.00    --  -88.50 -57.00   0.00  128
 44  \w   -140.00-111.00   0.50    2.00    --  -88.50 -77.00 120.00   58
 45  \w   -155.00-117.00   0.50    2.00    --  -88.50 -57.00 120.00   76
 46  \w   -160.00-119.00   0.50    2.00    --  -88.50 -38.00  60.00   82
 47  \w   -161.00-127.00   0.50    2.00    --  -88.50 -38.00  30.00   68
 48  \w   -157.00-125.00   0.50    2.00    --  -88.50 -77.00  90.00   64
 49  \w   -158.00-131.00   0.50    2.00    --  -88.50 -51.00 102.34   54
 50  \w   -159.00-101.00   0.50    2.00    --  -88.50 -77.00  60.00  116
 51  \w   -160.00 -65.00   0.50    2.00    --  -88.50 -77.00 -30.00  190
 52  \w    -81.00   1.00   0.50    0.50    --  -15.25 -57.00 -60.00  164
 53  \w    -74.00 -46.00   0.50    2.00    --  -88.50  98.00  92.00   56
 54  \w    -93.00 -47.00   0.50    2.00    --  -88.50 125.00 -30.00   92
 55  \w   -159.00-134.00   0.50    2.00    --  -88.50 -58.00-157.78   50
 56  \w   -159.00-112.00   0.50    2.00    --  -88.50 -77.00-180.00   94
 57  \w   -157.00-124.00   0.50    2.00    --  -88.50 -76.00 -81.11   66
 58  \w   -149.00-121.00   0.50    2.00    --  -88.50 -77.00 -90.00   56
 59  \w   -159.00-107.00   0.50    2.00    --  -88.50 -77.00-150.00  104
 60  \w   -159.00 -97.00   0.50    2.00    --  -88.50 -78.00 -54.80  124
 61  \w   -158.00-112.00   0.50    2.00    --  -88.50 -54.00-138.46   92
 62  \w     38.00 110.00   0.50    2.00    --  110.00 -99.00-150.00  144
 63  \w     93.00 125.00   0.50    2.00    --  110.00 -57.00-150.00   64
 64  \w     42.00  89.00   0.50    2.00    --  110.00 -57.00-150.00   94
 65  \w     43.00 127.00   0.50    2.00    --  110.00 -77.00-150.00  168
 66  \w    100.00 176.00   0.50    2.00    --  110.00  57.00 -30.00  152
 67  \w    122.00 149.00   0.50    2.00    --  110.00  98.00  92.00   54
 68  \w    126.00 175.00   0.50    2.00    --  110.00  77.00 -90.00   98
 69  \w     38.00  78.00   0.50    2.00    --  110.00-125.00  90.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1142747000
_diffrn_orient_matrix_UB_12      0.0186430000
_diffrn_orient_matrix_UB_13      -0.0962769000
_diffrn_orient_matrix_UB_21      -0.2248370000
_diffrn_orient_matrix_UB_22      -0.0050239000
_diffrn_orient_matrix_UB_23      -0.0779219000
_diffrn_orient_matrix_UB_31      0.0506901000
_diffrn_orient_matrix_UB_32      0.1328277000
_diffrn_orient_matrix_UB_33      0.0437868000
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15812
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.243
_diffrn_reflns_theta_min         3.769
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    3.318
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (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    1.430
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of hexane and ethyl acetate by slow evaporation'
_exptl_crystal_size_max          0.528
_exptl_crystal_size_mid          0.347
_exptl_crystal_size_min          0.332
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3230
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0442P)^2^+0.5324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3106
_reflns_number_total             3230
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02436_si_002.cif
_cod_data_source_block           idj24
_cod_depositor_comments          'Adding full bibliography for 1547133.cif.'
_cod_database_code               1547133
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C34 H40 Br2 N2 O8 '
_diffrn_oxdiff_ac3_digest_frames
;
01dcbf271839a66e1c4de191ae5e2d0c06056281a22
;
_diffrn_oxdiff_ac3_digest_hkl
;
01d67a6d27544d1f320d5bfc019cd61ef354cb
;
_reflns_odcompleteness_completeness 99.84
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H1-N1
 0.95 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C6(H6A,H6B), C16(H16A,H16B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C13(H13), C12(H12), C9(H9)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C17(H17A,H17B,H17C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id IDJ24
_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 2.072
_oxdiff_exptl_absorpt_empirical_full_min 0.584