A Modular and Concise Approach to MIDA Acylboronates via Chemoselective Oxidation of Unsymmetrical Geminal Diborylalkanes: Unlocking Access to a Novel Class of Acylborons
Lin, Shengjia; Wang, Lucia; Aminoleslami, Negin; Lao, Yanting; Yagel, Chelsea; Sharma, Abhishek; Chemical Science  (2019) –; doi:10.1039/C9SC00378A

data_1550773
_publ_section_title
;
 A Modular and Concise Approach to MIDA Acylboronates via Chemoselective
 Oxidation of Unsymmetrical Geminal Diborylalkanes: Unlocking Access to a
 Novel Class of Acylborons
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00378A
_journal_year                    2019
_chemical_formula_moiety         'C14 H22 B N O5'
_chemical_formula_sum            'C14 H22 B N O5'
_chemical_formula_weight         295.13
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-08-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-21 deposited with the CCDC.    2019-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.597(5)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   24.3090(11)
_cell_length_b                   6.3645(2)
_cell_length_c                   31.2582(14)
_cell_measurement_reflns_used    4160
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.0580
_cell_measurement_theta_min      3.8600
_cell_volume                     4527.0(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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     22.00  74.00   1.00    6.00    --   37.70 -99.00-150.00   52
  2  \w      6.00  33.00   1.00    6.00    --   37.70 -57.00  60.00   27
  3  \w    -59.00  32.00   1.00    6.00    --  -34.58  19.00-120.00   91
  4  \w    -64.00  35.00   1.00    6.00    --  -34.58  19.00 150.00   99
  5  \w     76.00 110.00   1.00    6.00    --   37.70 178.00-150.00   34
  6  \w    -51.00 -16.00   1.00    6.00    --  -37.78  37.00  60.00   35
  7  \w     -6.00  31.00   1.00    6.00    --  -37.78  37.00  60.00   37
  8  \w   -109.00 -82.00   1.00    6.00    --  -37.78-178.00-180.00   27
  9  \w     43.00 120.00   1.00   30.00    --  111.00 -45.00   0.00   77
 10  \w     73.00 178.00   1.00   30.00    --  111.00  15.00 -90.00  105
 11  \w     58.00 108.00   1.00   30.00    --  111.00 -94.00 -90.00   50
 12  \w    115.00 174.00   1.00   30.00    --  111.00 111.00  90.00   59
 13  \w     79.00 129.00   1.00   30.00    --  111.00 -61.00 -90.00   50
 14  \w     42.00 107.00   1.00   30.00    --  111.00 -94.00   0.00   65
 15  \w     44.00 125.00   1.00   30.00    --  111.00 -15.00-120.00   81
 16  \w    -53.00 -21.00   1.00    6.00    --  -37.78 -57.00 120.00   32
 17  \w    -88.00 -61.00   1.00    6.00    --  -37.78 -57.00 120.00   27
 18  \w    -69.00 -22.00   1.00    6.00    --  -37.78 -57.00-150.00   47
 19  \w   -104.00 -77.00   1.00    6.00    --  -37.78 -57.00-150.00   27
 20  \w    -97.00 -34.00   1.00    6.00    --  -37.78 178.00-150.00   63
 21  \w      1.00  68.00   1.00    6.00    --   37.78 -99.00  30.00   67
 22  \w    136.00 176.00   1.00   30.00    --  111.00  45.00-180.00   40
 23  \w     95.00 122.00   1.00   30.00    --  111.00 -45.00-180.00   27
 24  \w     51.00 129.00   1.00   30.00    --  111.00 -61.00 120.00   78
 25  \w     71.00 115.00   1.00   30.00    --  111.00-111.00  90.00   44
 26  \w     66.00  93.00   1.00   30.00    --  111.00 -45.00-180.00   27
 27  \w     48.00 132.00   1.00   30.00    --  111.00 -30.00  60.00   84
 28  \w     94.00 108.00   1.00   30.00    --  111.00  61.00  60.00   14
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0607862000
_diffrn_orient_matrix_UB_12      0.0089107000
_diffrn_orient_matrix_UB_13      -0.0049515000
_diffrn_orient_matrix_UB_21      -0.0295666000
_diffrn_orient_matrix_UB_22      -0.0109677000
_diffrn_orient_matrix_UB_23      -0.0523937000
_diffrn_orient_matrix_UB_31      -0.0035520000
_diffrn_orient_matrix_UB_32      0.2416360000
_diffrn_orient_matrix_UB_33      -0.0021720000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            29418
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.785
_diffrn_reflns_theta_min         3.885
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.714
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
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    1.299
_exptl_crystal_description       needle
_exptl_crystal_F_000             1896
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     571
_refine_ls_number_reflns         8883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0402P)^2^+0.1628P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5897
_reflns_number_total             8883
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00378a2.cif
_cod_data_source_block           lucia2
_cod_database_code               1550773
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'c14 h22 b n o5'
_reflns_odcompleteness_completeness 97.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     73.59
_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.a Ternary CH refined with riding coordinates:
 C5(H5), C5(H5), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B),
 C10(H10A,H10B), C14(H14A,H14B), C18(H18A,H18B), C3(H3A,H3B), C4(H4A,H4B),
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C14(H14A,
 H14B), C18(H18A,H18B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B),
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C14(H14A,H14B), C18(H18A,H18B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C13(H13A,H13B,H13C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              98684
_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 1.932
_oxdiff_exptl_absorpt_empirical_full_min 0.772