Diastereo- and enantioselective synthesis of biaryl aldehydes bearing both axial and central chirality.
Huang, Fen; Tao, Ling-Fei; Liu, Jiyong; Qian, Linghui; Liao, Jia-Yu; Chemical communications (Cambridge, England) 59 (2023) 4487–4490; doi:10.1039/d3cc00708a

data_7131447
_publ_section_title
;
 Diastereo- and enantioselective synthesis of biaryl aldehydes bearing
 both axial and central chirality.
;
_journal_issue                   30
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4487
_journal_page_last               4490
_journal_paper_doi               10.1039/d3cc00708a
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C41 H32 N O3 P'
_chemical_formula_sum            'C41 H32 N O3 P'
_chemical_formula_weight         617.64
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-12-09
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-13 deposited with the CCDC.	2023-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7964(3)
_cell_length_b                   25.0930(6)
_cell_length_c                   10.7544(3)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      67.80
_cell_measurement_theta_min      3.52
_cell_volume                     3723.10(16)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'zju Bruker D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            35451
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.122
_diffrn_reflns_theta_min         4.111
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.932
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1403 before and 0.0732 after correction.
The Ratio of minimum to maximum transmission is 0.7755.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
 Flack x determined using 2511 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         6754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0550P)^2^+0.0700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0882
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                6163
_reflns_number_total             6754
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00708a2.cif
_cod_data_source_block           cu_221208_hf_ph_model_dr_sq
_cod_depositor_comments
'Adding full bibliography for 7131446--7131447.cif.'
_cod_database_code               7131447
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.794
_shelx_estimated_absorpt_t_min   0.679
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11),
 C15(H15), C16(H16), C17(H17), C19(H19), C21(H21), C25(H25), C26(H26), C27(H27),
  C28(H28), C29(H29), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35),
 C37(H37), C38(H38), C39(H39), C40(H40), C41(H41)
;
_shelx_res_checksum              41322
_shelx_hkl_checksum              5043
_shelx_fab_checksum              57587
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'