α-Hydroxy boron-enabled regioselective access to bifunctional halo-boryl alicyclic ethers and α-halo borons.
Wang, Lucia; Lin, Shengjia; Zhu, Yawei; Ferrante, Daniel; Ishak, Timaf; Baba, Yuki; Sharma, Abhishek; Chemical communications (Cambridge, England) 57 (2021) 4564–4567; doi:10.1039/d1cc00336d

data_7128052
_publ_section_title
;
 \a-Hydroxy boron-enabled regioselective access to bifunctional halo-boryl
 alicyclic ethers and \a-halo borons.
;
_journal_issue                   37
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4564
_journal_page_last               4567
_journal_paper_doi               10.1039/d1cc00336d
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C11 H17 B Br N O5'
_chemical_formula_sum            'C11 H17 B Br N O5'
_chemical_formula_weight         333.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-12-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-01-12 deposited with the CCDC.	2021-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.149(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.7290(10)
_cell_length_b                   12.9542(7)
_cell_length_c                   13.1242(10)
_cell_measurement_reflns_used    1955
_cell_measurement_temperature    293.21(10)
_cell_measurement_theta_max      73.0490
_cell_measurement_theta_min      4.3120
_cell_volume                     2847.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.21(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_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      3.00  38.00   1.00    1.00    --    0.00 -99.00  30.00   35
  2  \w    -65.00 -37.00   1.00    1.00    --    0.00-178.00 -30.00   28
  3  \w    -69.00 -37.00   1.00    1.00    --    0.00-178.00-120.00   32
  4  \w      4.00  33.00   1.00    1.00    --    0.00 -99.00-150.00   29
  5  \w   -135.00 -96.00   1.00    2.55    --  -59.50 -94.00-120.00   39
  6  \w   -124.00 -91.00   1.00    2.55    --  -59.50 -94.00 -60.00   33
  7  \w   -121.00 -84.00   1.00    2.55    --  -59.50 -45.00-150.00   37
  8  \w     37.00 109.00   1.00    2.55    --   59.50  61.00-120.00   72
  9  \w     33.00 117.00   1.00    2.55    --   59.50-125.00  60.00   84
 10  \w      7.00  80.00   1.00    2.55    --   59.50 -61.00  30.00   73
 11  \w    123.00 148.00   1.00    2.55    --  119.00 178.00 -60.00   25
 12  \w    111.00 173.00   1.00    2.55    --  119.00  77.00 120.00   62
 13  \w    120.00 178.00   1.00    2.55    --  119.00  63.00-120.00   58
 14  \w     92.00 143.00   1.00    2.55    --  119.00  50.00 -30.00   51
 15  \w     53.00 112.00   1.00    2.55    --  119.00-111.00  30.00   59
 16  \w     51.00 104.00   1.00    2.55    --  119.00 -99.00 121.00   53
 17  \w    108.00 151.00   1.00    2.55    --  119.00 -77.00-180.00   43
 18  \w    101.00 176.00   1.00    2.55    --  119.00 111.00  30.00   75
 19  \w     47.00  88.00   1.00    2.55    --  119.00 -77.00-180.00   41
 20  \w     82.00 123.00   1.00    2.55    --  119.00 -77.00  90.00   41
 21  \w     46.00  87.00   1.00    2.55    --  119.00-111.00   0.00   41
 22  \w     85.00 176.00   1.00    2.55    --  119.00  77.00 -90.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0301628000
_diffrn_orient_matrix_UB_12      0.1121599000
_diffrn_orient_matrix_UB_13      0.0072685000
_diffrn_orient_matrix_UB_21      0.0111421000
_diffrn_orient_matrix_UB_22      -0.0113723000
_diffrn_orient_matrix_UB_23      -0.1110138000
_diffrn_orient_matrix_UB_31      -0.0861813000
_diffrn_orient_matrix_UB_32      0.0379396000
_diffrn_orient_matrix_UB_33      -0.0552721000
_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  0.0222
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5538
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.407
_diffrn_reflns_theta_min         4.315
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_description       Block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0585P)^2^+2.7634P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1377
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2322
_reflns_number_total             2857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00336d2.cif
_cod_data_source_block           exp_4247
_cod_depositor_comments
'Adding full bibliography for 7128050--7128052.cif.'
_cod_database_code               7128052
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H17 B1 Br1 N1 O5'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C009(H009), C00D(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00C(H00C,H00D), C00F(H00I,H00J), C00G(H00K,H00L), C00H(H00M,
 H00N), C00J(H00O,H00P)
2.c Idealised Me refined as rotating group:
 C00E(H00F,H00G,H00H)
;
_shelx_res_checksum              65626
_shelx_hkl_checksum              51239
_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 1.317
_oxdiff_exptl_absorpt_empirical_full_min 0.830