New P,N<sub>sp3</sub> ligands for palladium-catalyzed asymmetric allylic substitutions.
Su, Qin; Hou, Chuan-Jin; Wei, De-Quan; Qin, Hao; Liang, Ding-Hua; Hu, Xiang-Ping; Organic & biomolecular chemistry 21 (2023) 4874–4880; doi:10.1039/d3ob00519d

data_7159368
_publ_section_title
;
 New P,N<sub>sp3</sub> ligands for palladium-catalyzed asymmetric allylic
 substitutions.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4874
_journal_page_last               4880
_journal_paper_doi               10.1039/d3ob00519d
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C34 H32 N O P'
_chemical_formula_sum            'C34 H32 N O P'
_chemical_formula_weight         501.57
_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_creation_date             2019-10-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-01-31 deposited with the CCDC.	2023-05-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.277(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6002(16)
_cell_length_b                   15.401(3)
_cell_length_c                   10.5083(19)
_cell_measurement_reflns_used    8742
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      68.166
_cell_measurement_theta_min      2.869
_cell_volume                     1390.7(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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      298.15
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18211
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.189
_diffrn_reflns_theta_min         5.147
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.069
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1276 before and 0.0554 after correction. The Ratio of minimum to maximum transmission is 0.7582. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 2085 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.055(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4734
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0289
_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^)+(0.0489P)^2^+0.1076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0790
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_full    0.887
_reflns_Friedel_fraction_max     0.883
_reflns_number_gt                4674
_reflns_number_total             4734
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00519d2.cif
_cod_data_source_block           cu_20191015a_0m
_cod_depositor_comments          'Adding full bibliography for 7159368.cif.'
_cod_original_cell_volume        1390.8(4)
_cod_database_code               7159368
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.807
_shelx_estimated_absorpt_t_min   0.783
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10),
 C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C21(H21), C22(H22),
  C23(H23), C24(H24), C25(H25), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
2.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C)
;
_shelx_res_checksum              42486
_olex2_submission_special_instructions 'No special instructions were received'