Highly diastereoselective preparation of chiral NHC-boranes stereogenic at boron atom.
Chuzel, Olivier; Aupic, Clara; Abdou-Mohamed, Amel; Figliola, Calrlotta; Nava, Paola; Tuccio, Beatrice; Chouraqui, Gaëlle; Parrain, Jean-Luc; Chemical Science  (2019) –; doi:10.1039/C9SC01454C

data_1551144
_publ_section_title
;
 Highly diastereoselective preparation of chiral NHC-boranes stereogenic
 at boron atom.
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC01454C
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H29 B N2 O'
_chemical_formula_sum            'C23 H29 B N2 O'
_chemical_formula_weight         360.29
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-02-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-07-24 deposited with the CCDC.    2019-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.76550(10)
_cell_length_b                   12.17080(10)
_cell_length_c                   22.3907(2)
_cell_measurement_reflns_used    17277
_cell_measurement_temperature    293
_cell_measurement_theta_max      74.0600
_cell_measurement_theta_min      3.5650
_cell_volume                     2116.20(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (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_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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   -116.00 -17.00   1.00    2.00    --  -41.26 -38.00   0.00   99
  2  \w    -96.00  -2.00   1.00    2.00    --  -41.26 125.00 -60.00   94
  3  \w     23.00  97.00   1.00    2.00    --   41.26-125.00-180.00   74
  4  \w     25.00 109.00   1.00   10.00    --  107.87 -94.00  30.00   84
  5  \w     35.00 122.00   1.00   10.00    --  107.87-125.00-120.00   87
  6  \w     94.00 178.00   1.00   10.00    --  107.87 125.00 -60.00   84
  7  \w     75.00 178.00   1.00   10.00    --  107.87  77.00 120.00  103
  8  \w     55.00 178.00   1.00   10.00    --  107.87  15.00-120.00  123
  9  \w   -113.00 -13.00   1.00    2.00    --  -41.26 -57.00 -90.00  100
 10  \w   -113.00 -13.00   1.00    2.00    --  -41.26 -57.00 120.00  100
 11  \w     79.00 178.00   1.00   10.00    --  107.87  61.00  30.00   99
 12  \w     75.00 178.00   1.00   10.00    --  107.87  77.00  60.00  103
 13  \w     35.00 134.00   1.00   10.00    --  107.87 -45.00   0.00   99
 14  \w     82.00 178.00   1.00   10.00    --  107.87  45.00 -60.00   96
 15  \w   -117.00  -9.00   1.00    2.00    --  -41.26 -77.00-120.00  108
 16  \w      1.00  82.00   1.00    2.00    --   41.26 -99.00-120.00   81
 17  \w     82.00 178.00   1.00   10.00    --  107.87  45.00   0.00   96
 18  \w     75.00 178.00   1.00   10.00    --  107.87  77.00-120.00  103
 19  \w     75.00 146.00   1.00   10.00    --  107.87  77.00  90.00   71
 20  \w     25.00 109.00   1.00   10.00    --  107.87 -94.00 -90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1439946000
_diffrn_orient_matrix_UB_12      0.0127411000
_diffrn_orient_matrix_UB_13      -0.0467979000
_diffrn_orient_matrix_UB_21      0.1279845000
_diffrn_orient_matrix_UB_22      -0.0560952000
_diffrn_orient_matrix_UB_23      0.0428257000
_diffrn_orient_matrix_UB_31      -0.0474021000
_diffrn_orient_matrix_UB_32      -0.1127836000
_diffrn_orient_matrix_UB_33      -0.0265924000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            24338
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.440
_diffrn_reflns_theta_min         3.949
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
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    1.131
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/pentane'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         4258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0695P)^2^+0.1373P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1040
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4168
_reflns_number_total             4258
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01454c2.cif
_cod_data_source_block           ca609d
_cod_database_code               1551144
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c23 h29 b1 n2 o1'
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.817
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9(4)
 0.1(4)
2. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C5(H5), B1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C9(H9), C11(H11), C17(H17), C19(H19)
3.d Idealised Me refined as rotating group:
 C5AA(H5AA,H5AB,H5AC), C6(H6A,H6B,H6C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_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 1.574
_oxdiff_exptl_absorpt_empirical_full_min 0.665