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_1550774
_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         'C9 H12 B N O5'
_chemical_formula_sum            'C9 H12 B N O5'
_chemical_formula_weight         225.01
_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   geom
_audit_creation_date             2018-11-09
_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                78.441(3)
_cell_angle_beta                 85.514(3)
_cell_angle_gamma                63.232(3)
_cell_formula_units_Z            4
_cell_length_a                   10.3672(3)
_cell_length_b                   10.8231(3)
_cell_length_c                   10.9398(4)
_cell_measurement_reflns_used    5697
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      72.7220
_cell_measurement_theta_min      4.1251
_cell_volume                     1073.63(7)
_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      99.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_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    -88.00   1.00   1.00    1.00    --  -64.00  77.00 150.00   89
  2  \w      3.00  92.00   1.00    1.00    --   67.35 -77.00-120.00   89
  3  \w      3.00  92.00   1.00    1.00    --   67.35 -19.00   0.00   89
  4  \w     51.00 135.00   1.00    1.00    --   67.35  57.00   0.00   84
  5  \w    -93.00 -67.00   1.00    1.00    --  -37.78 178.00  90.00   26
  6  \w   -106.00 -71.00   1.00    1.00    --  -37.78-178.00 -90.00   35
  7  \w   -105.00 -73.00   1.00    1.00    --  -37.78 -37.00-120.00   32
  8  \w    -58.00 -19.00   1.00    1.00    --  -37.78 -37.00-120.00   39
  9  \w   -103.00 -12.00   1.00    1.00    --  -37.78 -77.00   0.00   91
 10  \w    -66.00 -40.00   1.00    1.00    --  -37.78 178.00  90.00   26
 11  \w     65.00  92.00   1.00    1.00    --   37.78-138.00-123.00   27
 12  \w    111.00 136.00   1.00    1.00    --  111.00 -77.00  60.00   25
 13  \w     44.00  87.00   1.00    1.00    --  111.00 -77.00  60.00   43
 14  \w     93.00 147.00   1.00    1.00    --  111.00 178.00 -30.00   54
 15  \w    112.00 137.00   1.00    1.00    --  111.00 -77.00  90.00   25
 16  \w    106.00 149.00   1.00    1.00    --  111.00  77.00-180.00   43
 17  \w     72.00  97.00   1.00    1.00    --  111.00 -94.00  60.00   25
 18  \w     69.00 112.00   1.00    1.00    --  111.00-111.00  30.00   43
 19  \w    100.00 126.00   1.00    1.00    --  111.00 178.00  60.00   26
 20  \w     58.00  84.00   1.00    1.00    --  111.00 -94.00 -90.00   26
 21  \w    112.00 172.00   1.00    1.00    --  111.00  45.00  60.00   60
 22  \w     57.00 107.00   1.00    1.00    --  111.00 -45.00 120.00   50
 23  \w     66.00 112.00   1.00    1.00    --  111.00-111.00 -90.00   46
 24  \w     58.00  90.00   1.00    1.00    --  111.00 178.00  60.00   32
 25  \w     64.00 116.00   1.00    1.00    --  111.00 -77.00-120.00   52
 26  \w    101.00 178.00   1.00    1.00    --  111.00  61.00  30.00   77
 27  \w     94.00 135.00   1.00    1.00    --  111.00 -15.00-120.00   41
 28  \w    133.00 178.00   1.00    1.00    --  111.00  30.00  90.00   45
 29  \w     43.00 127.00   1.00    1.00    --  111.00 -45.00 -90.00   84
 30  \w     42.00  68.00   1.00    1.00    --  111.00 -94.00  60.00   26
 31  \w    105.00 131.00   1.00    1.00    --  111.00  30.00  90.00   26
 32  \w     69.00 148.00   1.00    1.00    --  111.00 -15.00  60.00   79
 33  \w     50.00 107.00   1.00    1.00    --  111.00 -94.00 -60.00   57
 34  \w     59.00 100.00   1.00    1.00    --  111.00 -94.00 150.00   41
 35  \w     64.00 128.00   1.00    1.00    --  111.00 -45.00  30.00   64
 36  \w     49.00 101.00   1.00    1.00    --  111.00-111.00 150.00   52
 37  \w     56.00  81.00   1.00    1.00    --  111.00 -15.00-120.00   25
 38  \w    135.00 162.00   1.00    1.00    --  111.00  45.00 -30.00   27
 39  \w     74.00 100.00   1.00    1.00    --  111.00 -94.00  30.00   26
 40  \w     50.00  83.00   1.00    1.00    --  111.00 -25.00  43.75   33
 41  \w     42.00  67.00   1.00    1.00    --  111.00-111.00 120.00   25
 42  \w    114.00 143.00   1.00    1.00    --  111.00 111.00-180.00   29
 43  \w     78.00 103.00   1.00    1.00    --  111.00  15.00-180.00   25
 44  \w     44.00  90.00   1.00    1.00    --  111.00 -48.00-129.05   46
;
_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      0.0643856000
_diffrn_orient_matrix_UB_12      -0.1578280000
_diffrn_orient_matrix_UB_13      -0.0052934000
_diffrn_orient_matrix_UB_21      -0.0009068000
_diffrn_orient_matrix_UB_22      0.0356585000
_diffrn_orient_matrix_UB_23      -0.1436099000
_diffrn_orient_matrix_UB_31      0.1534914000
_diffrn_orient_matrix_UB_32      -0.0118906000
_diffrn_orient_matrix_UB_33      0.0035147000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11143
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.887
_diffrn_reflns_theta_min         4.125
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.951
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.493
_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    1.392
_exptl_crystal_description       irregular
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.156
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4233
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0682P)^2^+0.2831P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1190
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3853
_reflns_number_total             4233
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00378a2.cif
_cod_data_source_block           lucia3
_cod_original_cell_volume        1073.63(6)
_cod_database_code               1550774
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C9 H12 B O5 N'
_reflns_odcompleteness_completeness 99.74
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1A with sigma of 0.01 and sigma
for terminal atoms of 0.02
3. Same fragment restrains
{C1B, O2B, C3B, C4B, C5B, C1A, O2A, C3A, C4A, C5A, B6, N7, C8, C9, C10, O11,
O12, C13, C14, O15, O16} sigma for 1-2: 0.02, 1-3: 0.04
as
{C1A, O2A, C3A, C4A, C5A, C1B, O2B, C3B, C4B, C5B, B6, N7, C8, C9, C10, O11,
O12, C13, C14, O15, O16}
4. Others
 Sof(C1B)=Sof(O2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=Sof(H5B1)=
 Sof(H5B2)=Sof(H5B3)=1-FVAR(1)
 Sof(C1A)=Sof(O2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A1)=
 Sof(H5A2)=Sof(H5A3)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B), C29(H29A,H29B), C33(H33A,H33B)
5.b Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C3B(H3B), C4B(H4B), C23(H23), C24(H24)
5.c Idealised Me refined as rotating group:
 C5A(H5A1,H5A2,H5A3), C5B(H5B1,H5B2,H5B3), C8(H8A,H8B,H8C), C25(H25A,H25B,
 H25C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              55160
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.336
_oxdiff_exptl_absorpt_empirical_full_min 0.811