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_7126187
_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 H17 B Br N O5'
_chemical_formula_sum            'C14 H17 B Br N O5'
_chemical_formula_weight         370.02
_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'
_symmetry_Int_Tables_number      15
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-09-26 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.374(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.4754(5)
_cell_length_b                   6.47129(11)
_cell_length_c                   24.0236(6)
_cell_measurement_reflns_used    4211
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.2560
_cell_measurement_theta_min      4.0300
_cell_volume                     3041.07(14)
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.9978
_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     21.00  78.00   1.00    5.00    --   44.52  57.00-120.00   57
  2  \w     79.00 111.00   1.00    5.00    --   44.52  57.00-120.00   32
  3  \w     86.00 168.00   1.00   12.00    --  100.00  30.00 -30.00   82
  4  \w     77.00 106.00   1.00    5.00    --   44.52 125.00  90.00   29
  5  \w     28.00 126.00   1.00   12.00    --  100.00 -30.00 -30.00   98
  6  \w     82.00  96.00   1.00   12.00    --  100.00 -94.00   0.00   14
  7  \w     81.00 121.00   1.00   12.00    --  100.00 -77.00   0.00   40
  8  \w     60.00 120.00   1.00   12.00    --  100.00-125.00   0.00   60
  9  \w     26.00  52.00   1.00   12.00    --  100.00 -94.00   0.00   26
 10  \w     27.00  73.00   1.00   12.00    --  100.00 -77.00   0.00   46
 11  \w    -69.00  19.00   1.00    5.00    --  -44.52  57.00-180.00   88
 12  \w   -151.00 -96.00   1.00   12.00    --  -90.00-125.00 150.00   55
;
_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      -0.0126162000
_diffrn_orient_matrix_UB_12      -0.2344901000
_diffrn_orient_matrix_UB_13      -0.0087173000
_diffrn_orient_matrix_UB_21      0.0656365000
_diffrn_orient_matrix_UB_22      -0.0404716000
_diffrn_orient_matrix_UB_23      0.0579296000
_diffrn_orient_matrix_UB_31      -0.0416781000
_diffrn_orient_matrix_UB_32      0.0074981000
_diffrn_orient_matrix_UB_33      0.0390074000
_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  0.0243
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6092
_diffrn_reflns_theta_full        67.0742
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.04
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.894
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09602
_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_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.6162
_exptl_crystal_description       needle
_exptl_crystal_F_000             1503.0215
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.4472
_refine_diff_density_min         -0.5750
_refine_diff_density_rms         0.0778
_refine_ls_d_res_high            0.8370
_refine_ls_d_res_low             10.9412
_refine_ls_goodness_of_fit_ref   1.0609
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0609
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0276
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+2.3241P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0753
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              -25
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                2563
_reflns_number_total             2719
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0cc00722f2.cif
_cod_data_source_block           zyf_170608_2
_cod_depositor_comments
'Adding full bibliography for 7126186--7126187.cif.'
_cod_original_cell_volume        3041.05(13)
_cod_database_code               7126187
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.77
_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), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18a,H18b), C21(H21a,H21b)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C15(H15), C11(H11)
2.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C20(H20c,H20b,H20a)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_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 7.616
_oxdiff_exptl_absorpt_empirical_full_min 0.501