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_7131446
_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      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   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2c6m8h
_audit_creation_date             2022-04-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-22 deposited with the CCDC.	2023-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.337(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.582(4)
_cell_length_b                   14.754(3)
_cell_length_c                   15.384(4)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.45
_cell_volume                     3295.4(14)
_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 (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      170.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            14509
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.154
_diffrn_reflns_theta_min         1.916
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1070 before and 0.0624 after correction.
The Ratio of minimum to maximum transmission is 0.9463.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 5775 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     830
_refine_ls_number_reflns         14509
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0474P)^2^+0.3757P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0902
_reflns_Friedel_coverage         0.921
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                13309
_reflns_number_total             14509
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00708a2.cif
_cod_data_source_block           mo_220412_hf_0m_tw
_cod_depositor_comments
'Adding full bibliography for 7131446--7131447.cif.'
_cod_original_cell_volume        3295.6(14)
_cod_database_code               7131446
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8531(15)
 0.1469(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C22(H22), C63(H63)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C55(H55A,H55B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10),
 C11(H11), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C24(H24),
  C25(H25), C26(H26), C29(H29), C31(H31), C32(H32), C33(H33), C34(H34),
 C37(H37), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44),
  C45(H45), C46(H46), C49(H49), C50(H50), C51(H51), C52(H52), C53(H53),
 C57(H57), C58(H58), C59(H59), C60(H60), C61(H61), C62(H62), C65(H65), C66(H66),
  C67(H67), C70(H70), C72(H72), C73(H73), C74(H74), C75(H75), C78(H78),
 C79(H79), C80(H80), C81(H81), C82(H82)
;
_shelx_res_checksum              4835
_shelx_hkl_checksum              31015
_olex2_submission_special_instructions 'No special instructions were received'