Evolution of a 'privileged' P-alkene ligand: added planar chirality beats BINOL axial chirality in catalytic asymmetric C-C bond formation.
Leinauer, Luisa; Parla, Giorgio; Messelbeger, Julian; Herrera, Alberto; Heinemann, Frank W.; Langer, Jens; Chuchelkin, Ilya; Grasruck, Alexander; Frieß, Sibylle; Chelouan, Ahmed; Gavrilov, Konstantin; Dorta, Romano; Chemical communications (Cambridge, England)  (2023) –; doi:10.1039/d3cc04972h

data_7132372
_publ_section_title
;
 Evolution of a 'privileged' P-alkene ligand: added planar chirality beats
 BINOL axial chirality in catalytic asymmetric C-C bond formation.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc04972h
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C40 H29 B N O2 P'
_chemical_formula_sum            'C40 H29 B N O2 P'
_chemical_formula_weight         597.42
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2022-06-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-09-18 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.601(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8461(10)
_cell_length_b                   15.3010(19)
_cell_length_c                   13.0363(15)
_cell_measurement_reflns_used    9417
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.85
_cell_volume                     1547.4(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection       'Bruker APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2016)'
_computing_molecular_graphics    'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELX XT 2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa ImuS Duo Photon II CPAD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Quazar focussing montel optics'
_diffrn_radiation_source         'ImuS high brilliance micro-focus tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            119304
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.542
_diffrn_reflns_theta_min         2.625
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0879 before and 0.0579 after correction.
The Ratio of minimum to maximum transmission is 0.9023.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-heptane, 1,2-difluorobenzene'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 4286 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         9440
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0515P)^2^+0.2188P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0812
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                9154
_reflns_number_total             9440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04972h2.cif
_cod_data_source_block           rd2206
_cod_database_code               7132372
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.973
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All B(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C25(H25), C26(H26), C27(H27), C28(H28), C33(H33), C34(H34), C35(H35),
 C36(H36), C38(H38), C39(H39)
;
_shelx_res_checksum              67321
_shelx_hkl_checksum              94504
_olex2_submission_special_instructions 'No special instructions were received'