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_1551143
_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 ad
_chemical_formula_moiety         'C23 H29 B N2'
_chemical_formula_sum            'C23 H29 B N2'
_chemical_formula_weight         344.29
_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             2018-01-24
_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                   8.56120(10)
_cell_length_b                   15.4461(2)
_cell_length_c                   15.9652(3)
_cell_measurement_reflns_used    5377
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.8040
_cell_measurement_theta_min      5.6890
_cell_volume                     2111.19(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.988
_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     -4.00  22.00   1.00    1.00    --  -17.77 -19.00 120.00   26
  2  \w    -23.00  57.00   1.00    1.00    --  -17.77  38.00 -60.00   80
  3  \w    -89.00 -13.00   1.00    1.00    --  -17.77 -19.00 120.00   76
  4  \w     74.00 104.00   1.00    1.00    --   17.77-178.00 150.00   30
  5  \w     95.00 171.00   1.00   10.00    --  101.41 125.00   0.00   76
  6  \w     97.00 138.00   1.00   10.00    --  101.41 125.00-180.00   41
  7  \w     75.00 171.00   1.00   10.00    --  101.41  61.00  60.00   96
  8  \w    110.00 158.00   1.00   10.00    --  101.41 125.00-150.00   48
  9  \w     35.00  86.00   1.00   10.00    --  101.41-125.00  30.00   51
 10  \w     30.00 126.00   1.00   10.00    --  101.41 -45.00 -90.00   96
;
_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      0.0228231000
_diffrn_orient_matrix_UB_12      0.0153195000
_diffrn_orient_matrix_UB_13      0.0945465000
_diffrn_orient_matrix_UB_21      -0.1332759000
_diffrn_orient_matrix_UB_22      0.0669350000
_diffrn_orient_matrix_UB_23      -0.0010838000
_diffrn_orient_matrix_UB_31      -0.1187447000
_diffrn_orient_matrix_UB_32      -0.0723763000
_diffrn_orient_matrix_UB_33      0.0191069000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0128
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7375
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.053
_diffrn_reflns_theta_min         3.982
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.469
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.18b (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    1.083
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichlorometane/pentane'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
;
 Flack x determined using 1582 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0455
_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^)+(0.0756P)^2^+0.0757P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1107
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                3850
_reflns_number_total             3980
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01454c2.cif
_cod_data_source_block           ca582d
_cod_database_code               1551143
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c23 h29 b1 n2'
_shelx_estimated_absorpt_t_max   0.912
_shelx_estimated_absorpt_t_min   0.864
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C14(H14), B1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C15(H15A,H15B,
 H15C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_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 1.183
_oxdiff_exptl_absorpt_empirical_full_min 0.895