Synthesis of P-stereogenic 1-phosphanorbornane-derived phosphine–phosphite ligands and application in asymmetric catalysis
Ramazanova, Kyzgaldak; Chakrabortty, Soumyadeep; Müller, Bernd H.; Lönnecke, Peter; de Vries, Johannes G.; Hey-Hawkins, Evamarie; RSC Advances 13 (2023) 34439–34444; doi:10.1039/D3RA07630J

data_7247792
_publ_section_title
;
 Synthesis of P-stereogenic 1-phosphanorbornane-derived
 phosphine--phosphite ligands and application in asymmetric catalysis
;
_journal_issue                   49
_journal_name_full               'RSC Advances'
_journal_page_first              34439
_journal_page_last               34444
_journal_paper_doi               10.1039/D3RA07630J
_journal_volume                  13
_journal_year                    2023
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C30 H28 O4 P2 S2'
_chemical_formula_sum            'C30 H28 O4 P2 S2'
_chemical_formula_weight         578.58
_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'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-10-19 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.43040(10)
_cell_length_b                   16.7705(3)
_cell_length_c                   22.5342(3)
_cell_measurement_reflns_used    14382
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.2710
_cell_measurement_theta_min      2.5690
_cell_volume                     2808.02(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics
;
 ORTEP3 for Windows
 L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
 or
 DIAMOND Version 4.6.8
 K. Brandenburg, Crystal Impact GbR, Bonn, Germany
;
_computing_publication_material
;
 WINGX
 L.J. Farrugia,
 J. Appl. Cryst., 2012, 45, 849-854.
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SHELXT-2018-2
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 16.3560
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            39714
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.350
_diffrn_reflns_theta_max         27.712
_diffrn_reflns_theta_min         2.178
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 2058 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         6143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_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^)+(0.0337P)^2^+0.7984P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0813
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.906
_reflns_number_gt                5439
_reflns_number_total             6143
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra07630j2.cif
_cod_data_source_block           comp9b_x3698fin
_cod_database_code               7247792
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              57851