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_7129590
_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 H18 B Cl N2 O2 Si'
_chemical_formula_sum            'C16 H18 B Cl N2 O2 Si'
_chemical_formula_weight         344.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-09-04 deposited with the CCDC.	2022-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.750(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0522(6)
_cell_length_b                   12.5940(4)
_cell_length_c                   10.8967(4)
_cell_measurement_reflns_used    7304
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      74.6650
_cell_measurement_theta_min      3.6630
_cell_volume                     1696.13(12)
_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 1.000
_diffrn_measured_fraction_theta_max 0.961
_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    -85.00 -59.00   0.50    1.00    --  -42.05 -50.00 -12.00   52
  2  \w    -20.00   5.00   0.50    1.00    --  -42.05  19.00 -60.00   50
  3  \w    -60.00 -33.00   0.50    1.00    -- -102.00  61.00   0.00   54
  4  \w    -53.00 -28.00   0.50    1.00    -- -102.00  61.00 -30.00   50
  5  \w    -65.00 -39.00   0.50    1.00    -- -102.00  61.00 -90.00   52
  6  \w   -103.00 -65.00   0.50    1.00    -- -102.00  77.00-180.00   76
  7  \w   -175.00-129.00   0.50    1.00    -- -102.00 -50.00 -12.00   92
  8  \w   -172.00 -84.00   0.50    1.00    -- -102.00 -94.00  90.00  176
  9  \w    -53.00 -27.00   0.50    1.00    -- -102.00  50.00 134.00   52
 10  \w    -69.00 -44.00   0.50    1.00    -- -102.00  61.00 120.00   50
 11  \w    -31.00  50.00   0.50    1.00    --   42.05 -50.00 -12.00  162
 12  \w     18.00  57.00   0.50    1.00    --   42.05-125.00 -90.00   78
 13  \w     65.00  94.00   0.50    1.00    --   42.05-125.00 -90.00   58
 14  \w     32.00  59.00   0.50    1.00    --  106.13 -50.00 -12.00   54
 15  \w     33.00  98.00   0.50    1.00    --  106.13 -77.00   0.00  130
 16  \w     65.00  92.00   0.50    1.00    --  106.13 -94.00 -30.00   54
 17  \w     35.00  87.00   0.50    1.00    --  106.13 -94.00 -60.00  104
 18  \w     39.00  69.00   0.50    1.00    --  106.13 -61.00-150.00   60
 19  \w     34.00  59.00   0.50    1.00    --  106.13 -61.00-120.00   50
 20  \w     35.00  61.00   0.50    1.00    --  106.13 -94.00 -30.00   52
 21  \w     42.00  71.00   0.50    1.00    --  106.13 -61.00 120.00   58
 22  \w     20.00 117.00   0.50    1.00    --   42.05  50.00 134.00  194
 23  \w    103.00 173.00   0.50    1.00    --  106.13  50.00 134.00  140
 24  \w    127.00 174.00   0.50    1.00    --  106.13  45.00  60.00   94
 25  \w     93.00 118.00   0.50    1.00    --  106.13  45.00  60.00   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      -0.1184878000
_diffrn_orient_matrix_UB_12      0.0354645000
_diffrn_orient_matrix_UB_13      -0.0610159000
_diffrn_orient_matrix_UB_21      0.0320476000
_diffrn_orient_matrix_UB_22      0.0657008000
_diffrn_orient_matrix_UB_23      -0.1013512000
_diffrn_orient_matrix_UB_31      -0.0216993000
_diffrn_orient_matrix_UB_32      -0.0968992000
_diffrn_orient_matrix_UB_33      -0.0909637000
_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  0.0212
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10014
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.958
_diffrn_reflns_theta_min         3.576
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.749
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47761
_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    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.649
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0685P)^2^+1.2028P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1153
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3195
_reflns_number_total             3362
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc07002a2.cif
_cod_data_source_block           crl42-892_re
_cod_database_code               7129590
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.814
_shelx_estimated_absorpt_t_min   0.269
_reflns_odcompleteness_completeness 99.97
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C6(H6), C7(H7), C10(H10), C11(H11), C14(H14)
2.b Tetrahedral OH refined with riding coordinates:
 O2(H2)
2.c X=CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              14250
_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 1.484
_oxdiff_exptl_absorpt_empirical_full_min 0.502