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_7128050
_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         'C16 H19 B Br N O5'
_chemical_formula_sum            'C16 H19 B Br N O5'
_chemical_formula_weight         396.04
_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             2020-12-17
_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                 102.873(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8549(14)
_cell_length_b                   9.7346(7)
_cell_length_c                   10.8047(8)
_cell_measurement_reflns_used    1297
_cell_measurement_temperature    291.90(16)
_cell_measurement_theta_max      22.3620
_cell_measurement_theta_min      4.0990
_cell_volume                     1728.2(2)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.90(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.837
_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     40.00  73.00   1.00   12.50    --   17.04-138.00 176.00   33
  2  \w     42.00  76.00   1.00   12.50    --   17.04 178.00 150.00   34
  3  \w    -16.00  10.00   1.00   12.50    --   17.04 -37.00-180.00   26
  4  \w    -38.00  85.00   1.00   12.50    --   17.04   0.00  60.00  123
;
_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      -0.0384731000
_diffrn_orient_matrix_UB_12      0.0318063000
_diffrn_orient_matrix_UB_13      -0.0214046000
_diffrn_orient_matrix_UB_21      -0.0195158000
_diffrn_orient_matrix_UB_22      -0.0611144000
_diffrn_orient_matrix_UB_23      0.0131643000
_diffrn_orient_matrix_UB_31      0.0012864000
_diffrn_orient_matrix_UB_32      0.0237402000
_diffrn_orient_matrix_UB_33      0.0624795000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7907
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.423
_diffrn_reflns_theta_min         3.275
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.404
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91205
_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    1.522
_exptl_crystal_description       Needle
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1355
_refine_ls_R_factor_gt           0.0664
_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^)+(0.0513P)^2^+1.3302P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1582
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2160
_reflns_number_total             4000
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00336d2.cif
_cod_data_source_block           exp42241
_cod_depositor_comments
'Adding full bibliography for 7128050--7128052.cif.'
_cod_database_code               7128050
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C16 H19 B1 Br1 N1 O5'
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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), C00G(H00J), C00I(H00K)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00C(H00C,H00D), C00D(H00E,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C00K(H00O), C00M(H00P), C00N(H00Q), C00O(H00R)
2.d Idealised Me refined as rotating group:
 C00E(H00G,H00H,H00I), C00J(H00L,H00M,H00N)
;
_shelx_res_checksum              48866
_shelx_hkl_checksum              11892
_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 1.233
_oxdiff_exptl_absorpt_empirical_full_min 0.887