Synthesis of isoxazoloazaborines via gold(i)-catalyzed propargyl aza-Claisen rearrangement/borylative cyclization cascade
Tsuda, Masato; Morita, Taiki; Nakamura, Hiroyuki; Chemical Communications  (2022) –; doi:10.1039/D1CC07002A

data_7129591
_publ_section_title
;
 Synthesis of isoxazoloazaborines via gold(i)-catalyzed propargyl
 aza-Claisen rearrangement/borylative cyclization cascade
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC07002A
_journal_year                    2022
_chemical_formula_moiety         'C16 H20 B Cl N2 O3 Si'
_chemical_formula_sum            'C16 H20 B Cl N2 O3 Si'
_chemical_formula_weight         362.69
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2020-09-04 deposited with the CCDC.	2022-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                65.941(3)
_cell_angle_beta                 89.968(2)
_cell_angle_gamma                88.770(2)
_cell_formula_units_Z            4
_cell_length_a                   10.2669(3)
_cell_length_b                   12.8020(4)
_cell_length_c                   14.8879(4)
_cell_measurement_reflns_used    18278
_cell_measurement_temperature    90
_cell_measurement_theta_max      74.9710
_cell_measurement_theta_min      3.8350
_cell_volume                     1786.34(10)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.964
_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    -24.00  31.00   0.50    1.00    --  -42.05  19.00  30.00  110
  2  \w      5.00  39.00   0.50    1.00    --  -42.05  19.00 -30.00   68
  3  \w      0.00  25.00   0.50    1.00    --  -42.05  57.00  30.00   50
  4  \w    -67.00 -28.00   0.50    1.00    -- -102.00 103.00-133.00   78
  5  \w    -58.00 -32.00   0.50    1.00    -- -102.00  61.00-180.00   52
  6  \w    -64.00 -38.00   0.50    1.00    -- -102.00 125.00-120.00   52
  7  \w    -81.00 -17.00   0.50    1.00    --  -42.05 103.00-133.00  128
  8  \w     -1.00  32.00   0.50    1.00    --   42.05-103.00 124.00   66
  9  \w    -31.00  62.00   0.50    1.00    --   42.05 -57.00 150.00  186
 10  \w     58.00 140.00   0.50    1.00    --  106.13  15.00  90.00  164
 11  \w    147.00 178.00   0.50    1.00    --  106.13  15.00  90.00   62
 12  \w    110.00 168.00   0.50    1.00    --  106.13  45.00 -60.00  116
 13  \w     89.00 176.00   0.50    1.00    --  106.13 103.00-133.00  174
 14  \w     83.00 177.00   0.50    1.00    --  106.13  61.00 -30.00  188
 15  \w    117.00 171.00   0.50    1.00    --  106.13 125.00  90.00  108
 16  \w     72.00 107.00   0.50    1.00    --  106.13 -77.00-150.00   70
 17  \w     80.00 105.00   0.50    1.00    --  106.13 -94.00-120.00   50
 18  \w     37.00  99.00   0.50    1.00    --  106.13 -94.00-180.00  124
 19  \w     33.00  73.00   0.50    1.00    --  106.13 -61.00-150.00   80
 20  \w     35.00  68.00   0.50    1.00    --  106.13 -61.00 -90.00   66
 21  \w     41.00  66.00   0.50    1.00    --  106.13 -94.00-120.00   50
 22  \w     33.00  69.00   0.50    1.00    --  106.13 -61.00 -30.00   72
 23  \w     46.00  72.00   0.50    1.00    --  106.13 -77.00  30.00   52
 24  \w     46.00 105.00   0.50    1.00    --  106.13 -94.00  30.00  118
 25  \w     70.00 104.00   0.50    1.00    --  106.13 -77.00  90.00   68
 26  \w     80.00 105.00   0.50    1.00    --  106.13 -94.00 120.00   50
 27  \w     74.00 101.00   0.50    1.00    --  106.13-103.00 124.00   54
 28  \w     54.00 109.00   0.50    1.00    --  106.13-125.00  30.00  110
 29  \w     44.00  69.00   0.50    1.00    --  106.13 -94.00 120.00   50
 30  \w     37.00  62.00   0.50    1.00    --  106.13 -77.00  90.00   50
 31  \w    -38.00  21.00   0.50    1.00    --   42.05 -19.00  90.00  118
 32  \w    -37.00  27.00   0.50    1.00    --   42.05 -19.00-150.00  128
 33  \w   -107.00 -73.00   0.50    1.00    -- -102.00 103.00-133.00   68
 34  \w   -112.00 -80.00   0.50    1.00    -- -102.00 125.00-120.00   64
 35  \w    -63.00 -37.00   0.50    1.00    -- -102.00  61.00   0.00   52
 36  \w    -92.00 -54.00   0.50    1.00    -- -102.00 -15.00  60.00   76
 37  \w   -111.00 -86.00   0.50    1.00    -- -102.00-103.00 124.00   50
 38  \w   -105.00 -26.00   0.50    1.00    --  -42.05 -57.00  60.00  158
 39  \w   -143.00 -78.00   0.50    1.00    -- -102.00 -30.00-180.00  130
 40  \w   -175.00-149.00   0.50    1.00    -- -102.00 -30.00-180.00   52
 41  \w   -173.00 -96.00   0.50    1.00    -- -102.00 -15.00  60.00  154
 42  \w   -163.00-108.00   0.50    1.00    -- -102.00 -94.00  60.00  110
 43  \w   -107.00 -35.00   0.50    1.00    -- -102.00 107.00  39.91  144
;
_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      -0.0274695000
_diffrn_orient_matrix_UB_12      -0.0768626000
_diffrn_orient_matrix_UB_13      0.1085225000
_diffrn_orient_matrix_UB_21      0.0826040000
_diffrn_orient_matrix_UB_22      -0.0973131000
_diffrn_orient_matrix_UB_23      -0.0086561000
_diffrn_orient_matrix_UB_31      0.1222684000
_diffrn_orient_matrix_UB_32      0.0447128000
_diffrn_orient_matrix_UB_33      0.0314784000
_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  0.0183
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22024
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.993
_diffrn_reflns_theta_min         3.251
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83435
_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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         7092
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0470P)^2^+2.2721P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6824
_reflns_number_total             7092
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc07002a2.cif
_cod_data_source_block           crl42883
_cod_database_code               7129591
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.763
_shelx_estimated_absorpt_t_min   0.525
_reflns_odcompleteness_completeness 99.89
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21), C45(H45)
2.b Aromatic/amide H refined with riding coordinates:
 N33(H33), N9(H9), C12(H12), C35(H35), C11(H11), C14(H14), C15(H15), C36(H36),
 C39(H39), C38(H38)
2.c Idealised Me refined as rotating group:
 C47(H47A,H47B,H47C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C23(H23A,
 H23B,H23C)
2.d Idealised tetrahedral OH refined as rotating group:
 O48(H48), O46(H46), O22(H22), O24(H24)
;
_shelx_res_checksum              50675
_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 1.277
_oxdiff_exptl_absorpt_empirical_full_min 0.822