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_1551142
_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         'C24 H31 B N2'
_chemical_formula_sum            'C24 H31 B N2'
_chemical_formula_weight         358.32
_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             2017-10-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-07-17 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                   7.55860(10)
_cell_length_b                   9.20850(10)
_cell_length_c                   30.8403(5)
_cell_measurement_reflns_used    5675
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.7780
_cell_measurement_theta_min      4.3500
_cell_volume                     2146.59(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 0.999
_diffrn_measured_fraction_theta_max 0.985
_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    -98.00   4.00   1.00    1.00    --  -17.77 -19.00 -60.00  102
  2  \w    -78.00 -20.00   1.00    1.00    --  -17.77 -38.00-120.00   58
  3  \w     56.00  96.00   1.00    1.00    --   17.77-178.00-120.00   40
  4  \w     31.00 119.00   1.00   10.00    --  101.41 -61.00 -90.00   88
  5  \w    104.00 174.00   1.00   10.00    --  101.41 125.00 -30.00   70
  6  \w     95.00 121.00   1.00   10.00    --  101.41  30.00-120.00   26
  7  \w     30.00 130.00   1.00   10.00    --  101.41 -30.00  60.00  100
  8  \w    147.00 173.00   1.00   10.00    --  101.41  30.00-120.00   26
  9  \w     22.00 121.00   1.00   10.00    --  101.41 -15.00-180.00   99
;
_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      -0.1830659000
_diffrn_orient_matrix_UB_12      0.0614640000
_diffrn_orient_matrix_UB_13      0.0120733000
_diffrn_orient_matrix_UB_21      -0.0895794000
_diffrn_orient_matrix_UB_22      -0.1261723000
_diffrn_orient_matrix_UB_23      -0.0243856000
_diffrn_orient_matrix_UB_31      0.0006120000
_diffrn_orient_matrix_UB_32      -0.0909826000
_diffrn_orient_matrix_UB_33      0.0419084000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0112
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7385
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.926
_diffrn_reflns_theta_min         5.012
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.478
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90510
_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    1.109
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/pentane'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1575 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         4047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0687P)^2^+0.1637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                3944
_reflns_number_total             4047
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01454c2.cif
_cod_data_source_block           ca493d
_cod_database_code               1551142
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.902
_shelx_estimated_absorpt_t_min   0.854
_reflns_odcompleteness_completeness 99.81
_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:
 C4(H4), B3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C8(H8), C10(H10), C18(H18), C20(H20)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C)
;
_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 1.315
_oxdiff_exptl_absorpt_empirical_full_min 0.760