TfOH-Catalyzed Phosphinylation of 2,3-Allenols into γ-Ketophosphine Oxides.
Zhao, Runmin; Huang, Xianhua; Wang, Minning; Hu, Shanshan; Gao, Yuxing; Xu, Pengxiang; Zhao, Yufen; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00328

data_4038472
_publ_section_title
;
 TfOH-Catalyzed Phosphinylation of 2,3-Allenols into \g-Ketophosphine
 Oxides.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00328
_journal_year                    2020
_chemical_formula_moiety         'C22 H20 Br O2 P'
_chemical_formula_sum            'C22 H20 Br O2 P'
_chemical_formula_weight         427.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                86.194(3)
_cell_angle_beta                 88.953(4)
_cell_angle_gamma                75.743(3)
_cell_formula_units_Z            2
_cell_length_a                   5.6728(12)
_cell_length_b                   9.823(2)
_cell_length_c                   17.884(4)
_cell_measurement_reflns_used    4789
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.60
_cell_measurement_theta_min      2.28
_cell_volume                     963.7(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_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      100.00(10)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.8814
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       "'\w scans"
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8185
_diffrn_reflns_theta_full        28.6202
_diffrn_reflns_theta_max         28.62
_diffrn_reflns_theta_min         1.14
_exptl_absorpt_coefficient_mu    2.229
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.452606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.1511 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.4526.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4724
_exptl_crystal_description       block
_exptl_crystal_F_000             435.8197
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.0554
_refine_diff_density_min         -0.8413
_refine_diff_density_rms         0.1165
_refine_ls_d_res_high            0.7419
_refine_ls_d_res_low             17.8440
_refine_ls_goodness_of_fit_ref   1.0454
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    37
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0454
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0811P)^2^+0.7775P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1540
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                3849
_reflns_number_total             4370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00328_si_001.cif
_cod_data_source_block           P
_cod_database_code               4038472
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 C1(H1), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C12(H12), C16(H16), C13(H13), C15(H15), C18(H18), C7(H7),
 C8(H8), C6(H6), C20(H20), C21(H21), C19(H19)
2.d Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c)
;
_olex2_submission_special_instructions 'No special instructions were received'