Zn(OTf)2-Catalyzed Phosphinylation of Propargylic Alcohols: Access to γ-Ketophosphine Oxides.
Shan, Changkai; Chen, Fushan; Pan, Jiaoting; Gao, Yuxing; Xu, Pengxiang; Zhao, Yufen; The Journal of organic chemistry 82 (2017) 11659–11666; doi:10.1021/acs.joc.7b02164

data_4033023
_publ_section_title
;
 Zn(OTf)2-Catalyzed Phosphinylation of Propargylic Alcohols: Access to
 \g-Ketophosphine Oxides.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11659
_journal_page_last               11666
_journal_paper_doi               10.1021/acs.joc.7b02164
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C27 H22 Cl O2 P'
_chemical_formula_sum            'C27 H22 Cl O2 P'
_chemical_formula_weight         444.86
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_cell_angle_alpha                88.572(6)
_cell_angle_beta                 88.944(6)
_cell_angle_gamma                76.822(6)
_cell_formula_units_Z            2
_cell_length_a                   5.710(2)
_cell_length_b                   9.405(3)
_cell_length_c                   20.359(7)
_cell_measurement_reflns_used    3317
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.42
_cell_volume                     1064.1(6)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_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      273.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8313
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_min         1.001
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.781418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0958 before and 0.0425 after correction.
The Ratio of minimum to maximum transmission is 0.7814.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0650P)^2^+0.4850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1426
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3410
_reflns_number_total             4098
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02164_si_002.cif
_cod_data_source_block           p
_cod_depositor_comments          'Adding full bibliography for 4033023.cif.'
_cod_database_code               4033023
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.874
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C21(H21), C11(H11), C14(H14), C15(H15), C12(H12), C23(H23),
 C17(H17), C26(H26), C25(H25), C5(H5), C9(H9), C24(H24), C19(H19), C18(H18),
 C20(H20), C8(H8), C7(H7), C6(H6)
;
_shelx_res_checksum              34572
_shelx_hkl_checksum              25615
_olex2_submission_special_instructions 'No special instructions were received'