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_7128051
_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         'C15 H17 B Br N O5'
_chemical_formula_sum            'C15 H17 B Br N O5'
_chemical_formula_weight         382.01
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-01-12 deposited with the CCDC.	2021-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.7731(8)
_cell_length_b                   6.9423(4)
_cell_length_c                   40.482(3)
_cell_measurement_reflns_used    2916
_cell_measurement_temperature    292.11(19)
_cell_measurement_theta_max      59.3940
_cell_measurement_theta_min      4.3720
_cell_volume                     3308.7(4)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.11(19)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1098
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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    -81.00 -46.00   1.00    1.08    --    0.00 178.00 120.00   35
  2  \w      2.00  36.00   1.00    1.08    --    0.00 -99.00 -30.00   34
  3  \w      1.00  39.00   1.00    1.08    --    0.00 -99.00-180.00   38
  4  \w    -33.00  -5.00   1.00    1.08    --    0.00  77.00 120.00   28
  5  \w     28.00  70.00   1.00    1.08    --    0.00  77.00 120.00   42
  6  \w      4.00  29.00   1.00    1.08    --    0.00 -99.00 150.00   25
  7  \w    -82.00 -35.00   1.00    1.08    --    0.00-178.00 -60.00   47
  8  \w   -115.00 -80.00   1.00    4.34    --  -59.50 -94.00 -60.00   35
  9  \w   -131.00 -80.00   1.00    4.34    --  -59.50 -94.00-120.00   51
 10  \w   -132.00 -83.00   1.00    4.34    --  -59.50 -94.00 -90.00   49
 11  \w    -73.00 -45.00   1.00    4.34    --  -59.50 125.00 -90.00   28
 12  \w   -132.00-103.00   1.00    4.34    --  -59.50-125.00-150.00   29
 13  \w   -129.00 -87.00   1.00    4.34    --  -59.50 -94.00-150.00   42
 14  \w    -84.00 -13.00   1.00    4.34    --  -59.50  73.00  90.00   71
 15  \w     41.00 129.00   1.00    4.34    --   59.50  61.00 -60.00   88
 16  \w    -11.00  35.00   1.00    4.34    --   59.50 -77.00 120.00   46
 17  \w     42.00 117.00   1.00    4.34    --   59.50-125.00-180.00   75
 18  \w     -6.00  25.00   1.00    4.34    --   59.50 -61.00 150.00   31
 19  \w     33.00  83.00   1.00    4.34    --   59.50 -61.00 150.00   50
 20  \w     10.00  87.00   1.00    4.34    --   59.50 -45.00 150.00   77
 21  \w     85.00 112.00   1.00    4.34    --  119.00-111.00 120.00   27
 22  \w    136.00 178.00   1.00    4.34    --  119.00  73.00  90.00   42
 23  \w     94.00 121.00   1.00    4.34    --  119.00  73.00  90.00   27
 24  \w    100.00 145.00   1.00    4.34    --  119.00 -37.00  30.00   45
 25  \w    113.00 161.00   1.00    4.34    --  119.00 -91.00 -30.00   48
 26  \w     44.00 177.00   1.00    4.34    --  119.00   0.00-150.00  133
 27  \w     49.00 144.00   1.00    4.34    --  119.00 -63.00 120.00   95
 28  \w     44.00 150.00   1.00    4.34    --  119.00 -25.00 -90.00  106
 29  \w     88.00 122.00   1.00    4.34    --  119.00  77.00 -90.00   34
 30  \w     61.00 109.00   1.00    4.34    --  119.00-111.00 -60.00   48
 31  \w     48.00 147.00   1.00    4.34    --  119.00 -50.00 -60.00   99
 32  \w     53.00  86.00   1.00    4.34    --  119.00 -91.00 -30.00   33
 33  \w     73.00 112.00   1.00    4.34    --  119.00-111.00-120.00   39
 34  \w     86.00 177.00   1.00    4.34    --  119.00  25.00-120.00   91
 35  \w     88.00 149.00   1.00    4.34    --  119.00 -37.00 120.00   61
 36  \w     69.00 112.00   1.00    4.34    --  119.00-111.00  30.00   43
 37  \w     86.00 111.00   1.00    4.34    --  119.00-111.00 -30.00   25
 38  \w     43.00 112.00   1.00    4.34    --  119.00-111.00 150.00   69
 39  \w    144.00 175.00   1.00    4.34    --  119.00 111.00-180.00   31
 40  \w     48.00  82.00   1.00    4.34    --  119.00-111.00 -30.00   34
 41  \w    131.00 174.00   1.00    4.34    --  119.00  77.00 -90.00   43
 42  \w     53.00  87.00   1.00    4.34    --  119.00 -37.00 120.00   34
 43  \w     83.00 157.00   1.00    4.34    --  119.00 -91.00 150.00   74
;
_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      0.0700130000
_diffrn_orient_matrix_UB_12      -0.0948696000
_diffrn_orient_matrix_UB_13      -0.0277071000
_diffrn_orient_matrix_UB_21      0.0306218000
_diffrn_orient_matrix_UB_22      0.2006663000
_diffrn_orient_matrix_UB_23      -0.0136747000
_diffrn_orient_matrix_UB_31      0.1061860000
_diffrn_orient_matrix_UB_32      0.0050911000
_diffrn_orient_matrix_UB_33      0.0221988000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            22840
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.071
_diffrn_reflns_theta_min         4.369
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57107
_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_density_diffrn    1.534
_exptl_crystal_description       Block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.873
_refine_diff_density_min         -0.721
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details
;
 Flack x determined using 1531 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.32(3)
_refine_ls_extinction_coef       0.00031(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         6312
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0832
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0950P)^2^+12.0558P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2259
_refine_ls_wR_factor_ref         0.2401
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.887
_reflns_Friedel_fraction_max     0.876
_reflns_number_gt                4919
_reflns_number_total             6312
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00336d2.cif
_cod_data_source_block           exp_4258
_cod_depositor_comments
'Adding full bibliography for 7128050--7128052.cif.'
_cod_database_code               7128051
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C15 H17 B1 Br1 N1 O5'
_reflns_odcompleteness_completeness 99.92
_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:
 C00G(H00H), C00J(H00J), C00N(H00N), C00U(H00U), C00W(H00W), C016(H016)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00I,H00K), C00M(H00M,H00O), C00O(H00A,H00B), C00P(H00P,H00Q), C00V(H00F,
 H00G), C011(H01A,H01B)
2.c Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00Q(H00R), C00X(H00X), C00Y(H00Y), C010(H010), C014(H014),
 C017(H017), C018(H018), C019(H019), C01A(H01C)
2.d Idealised Me refined as rotating group:
 C00S(H00C,H00D,H00E), C00Z(H00S,H00T,H00V)
;
_shelx_res_checksum              29602
_shelx_hkl_checksum              60703
_olex2_date_sample_data_collection 2020-12-29
_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 1.625
_oxdiff_exptl_absorpt_empirical_full_min 0.639