Palladium-catalyzed regio- and enantio-selective trifluoromethylated allylic alkylation of diphenylphosphine oxides.
Zhang, Shuaibo; Liu, Yunzhe; Sun, Luyang; Wang, Bangzhong; Zhao, Jinfeng; Qu, Jingping; Zhou, Yuhan; Organic & biomolecular chemistry 23 (2025) 4457–4462; doi:10.1039/d5ob00096c

data_7160460
_publ_section_title
;
 Palladium-catalyzed regio- and enantio-selective trifluoromethylated
 allylic alkylation of diphenylphosphine oxides.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4457
_journal_page_last               4462
_journal_paper_doi               10.1039/d5ob00096c
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H24 F3 O3 P'
_chemical_formula_sum            'C25 H24 F3 O3 P'
_chemical_formula_weight         460.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-09-04
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-01-11 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.948(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.608(3)
_cell_length_b                   5.6779(7)
_cell_length_c                   18.838(2)
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    307.00
_cell_measurement_theta_max      72.37
_cell_measurement_theta_min      4.21
_cell_volume                     2365.8(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      307.00
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0336
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26124
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.431
_diffrn_reflns_theta_min         2.397
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.445
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5916
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1419 before and 0.0601 after correction.
The Ratio of minimum to maximum transmission is 0.7850.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1759 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.043(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4499
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0796P)^2^+0.2785P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1189
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                4239
_reflns_number_total             4499
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00096c2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7160460.cif.'
_cod_database_code               7160460
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.869
_shelx_estimated_absorpt_t_min   0.761
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O00J-C00Q \\sim O00K-C00Q
 with sigma of 0.02
 O00J-C1 \\sim O00K-C1A
 with sigma of 0.02
 C00Q-C1 \\sim C00Q-C1A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O00J \\sim C1 \\sim O00K \\sim C1A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 O00J, C00Q, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C00Q, O00K, C1A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(O00K)=Sof(C1A)=Sof(H1Aa)=Sof(H1Ab)=Sof(H1Ac)=1-FVAR(1)
 Sof(O00J)=Sof(C1)=Sof(H1a)=Sof(H1b)=Sof(H1c)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C004(H004)
6.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H), C00K(H00K), C00L(H00L), C00M(H00M),
 C00O(H00O), C00P(H00P)
6.c Idealised Me refined as rotating group:
 C00S(H00i,H00j,H00n), C00T(H00q,H00r,H00s), C1(H1a,H1b,H1c), C1A(H1Aa,H1Ab,
 H1Ac)
;
_shelx_res_checksum              22690
_olex2_submission_special_instructions 'No special instructions were received'