Halohydroxylation of alkenyl MIDA boronates: switchable stereoselectivity induced by B(MIDA) substituent.
Zeng, Yao-Fu; Liu, Xu-Ge; Tan, Dong-Hang; Fan, Wen-Xin; Li, Yi-Na; Guo, Yu; Wang, Honggen; Chemical communications (Cambridge, England) 56 (2020) 4332–4335; doi:10.1039/d0cc00722f

data_7126186
_publ_section_title
;
 Halohydroxylation of alkenyl MIDA boronates: switchable stereoselectivity
 induced by B(MIDA) substituent.
;
_journal_issue                   31
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4332
_journal_page_last               4335
_journal_paper_doi               10.1039/d0cc00722f
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C14 H16 B F I N O5, C3 H6 O'
_chemical_formula_sum            'C17 H22 B F I N O6'
_chemical_formula_weight         493.09
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-01-10 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.1114(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.3516(3)
_cell_length_b                   11.2310(2)
_cell_length_c                   10.6444(2)
_cell_measurement_reflns_used    5155
_cell_measurement_theta_max      71.9860
_cell_measurement_theta_min      2.6380
_cell_volume                     1992.86(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2008 (Burla et al., 2007)'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9674
_diffrn_measured_fraction_theta_max 0.9674
_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    -26.00  69.00   1.00    2.00    --   44.40 -37.00  30.00   95
  2  \w     31.00  91.00   1.00    5.00    --  100.00 -94.00   0.00   60
  3  \w     79.00 108.00   1.00    5.00    --  100.00-125.00-180.00   29
  4  \w     74.00 168.00   1.00    5.00    --  100.00  61.00  30.00   94
  5  \w    126.00 166.00   1.00    5.00    --  100.00  77.00  60.00   40
  6  \w     99.00 170.00   1.00    5.00    --  100.00  61.00  90.00   71
  7  \w     69.00 116.00   1.00    5.00    --  100.00  77.00  60.00   47
  8  \w    -67.00 -26.00   1.00    2.00    --  -44.40 -57.00   0.00   41
  9  \w   -106.00 -81.00   1.00    2.00    --  -44.40-125.00  60.00   25
 10  \w   -111.00 -86.00   1.00    2.00    --  -44.40 -57.00   0.00   25
 11  \w   -117.00 -74.00   1.00    2.00    --  -44.40-125.00-150.00   43
 12  \w   -101.00 -56.00   1.00    5.00    --  -90.00 125.00-150.00   45
 13  \w   -102.00 -75.00   1.00    5.00    --  -90.00  61.00-120.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0376291000
_diffrn_orient_matrix_UB_12      -0.0954929000
_diffrn_orient_matrix_UB_13      -0.0685811000
_diffrn_orient_matrix_UB_21      -0.0588421000
_diffrn_orient_matrix_UB_22      -0.0931995000
_diffrn_orient_matrix_UB_23      0.0261011000
_diffrn_orient_matrix_UB_31      -0.0605666000
_diffrn_orient_matrix_UB_32      0.0312479000
_diffrn_orient_matrix_UB_33      -0.1316223000
_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  0.0629
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7761
_diffrn_reflns_theta_full        67.0784
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         2.65
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    13.004
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.04111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.6433
_exptl_crystal_F_000             986.6074
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         3.6026
_refine_diff_density_min         -1.7467
_refine_diff_density_rms         0.2292
_refine_ls_d_res_high            0.8370
_refine_ls_d_res_low             16.6701
_refine_ls_goodness_of_fit_ref   1.0517
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0517
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0806
_refine_ls_shift/su_max          3.4534
_refine_ls_shift/su_mean         0.0637
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1802P)^2^+3.8146P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2272
_refine_ls_wR_factor_ref         0.2355
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -20
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                3147
_reflns_number_total             3447
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0cc00722f2.cif
_cod_data_source_block           zyf_IOH_160919_2_2
_cod_depositor_comments
'Adding full bibliography for 7126186--7126187.cif.'
_cod_original_cell_volume        1992.86(7)
_cod_database_code               7126186
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 96.10
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C14(H14a,H14b)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C23(H23), C19(H19)
2.d Idealised Me refined as rotating group:
 C11(H11b,H11a,H11c), C18(H18a,H18b,H18c), C25(H25a,H25b,H25c), C2(H2a,H2b,H2c)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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 13.281
_oxdiff_exptl_absorpt_empirical_full_min 0.396