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_1550775
_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         'C7 H10 B N O6'
_chemical_formula_sum            'C7 H10 B N O6'
_chemical_formula_weight         214.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-01 deposited with the CCDC.    2019-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.438(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.3307(3)
_cell_length_b                   21.4147(8)
_cell_length_c                   9.6557(4)
_cell_measurement_reflns_used    4951
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.6460
_cell_measurement_theta_min      4.1400
_cell_volume                     1819.38(13)
_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)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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 0.997
_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    -71.00  -6.00   1.00    5.00    --  -64.00  57.00-120.00   65
  2  \w     61.00 125.00   1.00    1.00    --   67.35  57.00  60.00   64
  3  \w   -104.00 -58.00   1.00    1.00    --  -37.78 -57.00-120.00   46
  4  \w    -29.00  30.00   1.00    1.00    --  -37.78  57.00-150.00   59
  5  \w   -102.00 -74.00   1.00    1.00    --  -37.78-178.00-180.00   28
  6  \w    -68.00 -42.00   1.00    1.00    --  -37.78-178.00-180.00   26
  7  \w     29.00  75.00   1.00    1.00    --   37.78 -99.00-120.00   46
  8  \w     76.00 103.00   1.00    1.00    --   37.78  77.00 120.00   27
  9  \w     11.00  55.00   1.00    1.00    --   37.78  77.00 120.00   44
 10  \w     45.00  72.00   1.00    5.00    --  111.00-111.00  60.00   27
 11  \w    121.00 177.00   1.00    5.00    --  111.00  15.00-120.00   56
 12  \w     85.00 114.00   1.00    5.00    --  111.00  77.00-150.00   29
 13  \w    119.00 177.00   1.00    5.00    --  111.00  45.00  90.00   58
 14  \w     44.00  98.00   1.00    5.00    --  111.00 -94.00-180.00   54
 15  \w     41.00 113.00   1.00    5.00    --  111.00-111.00 150.00   72
 16  \w     89.00 115.00   1.00    5.00    --  111.00 -61.00 150.00   26
 17  \w     64.00  90.00   1.00    5.00    --  111.00-111.00 -90.00   26
 18  \w     71.00 109.00   1.00    5.00    --  111.00 -94.00-150.00   38
 19  \w     73.00 122.00   1.00    5.00    --  111.00-138.00 -22.00   49
 20  \w    139.00 177.00   1.00    5.00    --  111.00  77.00 -30.00   38
 21  \w     41.00  68.00   1.00    5.00    --  111.00-111.00  90.00   27
 22  \w     59.00  87.00   1.00    5.00    --  111.00 -61.00 150.00   28
 23  \w     97.00 122.00   1.00    5.00    --  111.00  77.00 -30.00   25
 24  \w     79.00 128.00   1.00    5.00    --  111.00 -30.00 150.00   49
 25  \w    132.00 174.00   1.00    5.00    --  111.00  77.00-150.00   42
 26  \w     53.00  94.00   1.00    5.00    --  111.00 -94.00 150.00   41
 27  \w     98.00 137.00   1.00    5.00    --  111.00 178.00   0.00   39
 28  \w     94.00 159.00   1.00    5.00    --  111.00  61.00 150.00   65
;
_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      -0.0191355000
_diffrn_orient_matrix_UB_12      -0.0711935000
_diffrn_orient_matrix_UB_13      -0.0207230000
_diffrn_orient_matrix_UB_21      0.1506372000
_diffrn_orient_matrix_UB_22      -0.0100749000
_diffrn_orient_matrix_UB_23      0.1267822000
_diffrn_orient_matrix_UB_31      -0.0872708000
_diffrn_orient_matrix_UB_32      -0.0017819000
_diffrn_orient_matrix_UB_33      0.1101435000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10819
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.808
_diffrn_reflns_theta_min         4.129
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.176
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.700
_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    1.570
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.397
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3609
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0591P)^2^+0.5913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3155
_reflns_number_total             3609
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00378a2.cif
_cod_data_source_block           shengjia2
_cod_original_cell_volume        1819.38(12)
_cod_database_code               1550775
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C7 H10 B N O6'
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C9(H9A,H9B), C25(H25A,H25B), C29(H29A,H29B)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C31(H31A,H31B,H31C), C35(H35A,H35B,
 H35C)
;
_shelx_res_checksum              86426
_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 1.949
_oxdiff_exptl_absorpt_empirical_full_min 0.755