Copper-Catalyzed Direct Coupling of Unprotected Propargylic Alcohols with P(O)H Compounds: Access to Allenylphosphoryl Compounds under Ligand- and Base-Free Conditions.
Hu, Gaobo; Shan, Changkai; Chen, Weizhu; Xu, Pengxiang; Gao, Yuxing; Zhao, Yufen; Organic letters 18 (2016) 6066–6069; doi:10.1021/acs.orglett.6b03028

data_1555925
_publ_section_title
;
 Copper-Catalyzed Direct Coupling of Unprotected Propargylic Alcohols with
 P(O)H Compounds: Access to Allenylphosphoryl Compounds under Ligand- and
 Base-Free Conditions.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6066
_journal_page_last               6069
_journal_paper_doi               10.1021/acs.orglett.6b03028
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C27 H20 F O P'
_chemical_formula_sum            'C27 H20 F O P'
_chemical_formula_weight         410.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.040(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.104(4)
_cell_length_b                   9.075(3)
_cell_length_c                   27.414(10)
_cell_measurement_reflns_used    7584
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.02
_cell_measurement_theta_min      2.34
_cell_volume                     2762.0(17)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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     0.710
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            20271
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.484
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9570
_exptl_absorpt_correction_T_min  0.9165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.1583 before and 0.0489 after correction.
The Ratio of minimum to maximum transmission is 0.7992.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.987
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_platon_squeeze_details
;
SQUEEZE removed one disordered dichloromethane and one disordered chloroform molecules per formula unit.
;
_refine_diff_density_max         0.818
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0784
_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^)+(0.1260P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1998
_refine_ls_wR_factor_ref         0.2094
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3900
_reflns_number_total             5438
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03028_si_002.cif
_cod_data_source_block           p
_cod_original_cell_volume        2762.1(17)
_cod_database_code               1555925
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C27(H27), C9(H9), C21(H21), C23(H23), C8(H8), C26(H26), C11(H11),
 C20(H20), C25(H25), C7(H7), C24(H24), C15(H15), C12(H12), C5(H5), C19(H19),
 C14(H14), C6(H6), C17(H17), C18(H18)
;
_shelx_res_checksum              57610
_shelx_hkl_checksum              95700
_olex2_submission_special_instructions 'No special instructions were received'