Intramolecular, Pd/Cu-Co-catalyzed P-C Bond Cleavage and Addition onto an Alkyne: A Route to Benzophospholes.
Zhou, Yang; Gan, Zhenjie; Su, Bo; Li, Jun; Duan, Zheng; Mathey, François; Organic letters 17 (2015) 5722–5724; doi:10.1021/acs.orglett.5b02926

data_1540625
_publ_section_title
;
 Intramolecular, Pd/Cu-Co-catalyzed P-C Bond Cleavage and Addition onto an
 Alkyne: A Route to Benzophospholes.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5722
_journal_page_last               5724
_journal_paper_doi               10.1021/acs.orglett.5b02926
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C32 H21 O5 P W'
_chemical_formula_sum            'C32 H21 O5 P W'
_chemical_formula_weight         700.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-31
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_length_b                   11.9824(4)
_cell_length_c                   20.3830(6)
_cell_measurement_reflns_used    4899
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.0170
_cell_measurement_theta_min      3.3300
_cell_volume                     2786.34(16)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
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_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -22.00   24.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2104  -99.0000   90.0000 46

  2 omega   41.00   81.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  178.0000   90.0000 40

  3 omega   -7.00   27.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885   77.0000  -30.0000 34

  4 omega  -23.00   90.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885   19.0000 -150.0000 113
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
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_diffrn_orient_matrix_UB_12      -0.0559802000
_diffrn_orient_matrix_UB_13      -0.0113718000
_diffrn_orient_matrix_UB_21      -0.0284846000
_diffrn_orient_matrix_UB_22      -0.0144513000
_diffrn_orient_matrix_UB_23      0.0275011000
_diffrn_orient_matrix_UB_31      -0.0549828000
_diffrn_orient_matrix_UB_32      0.0128184000
_diffrn_orient_matrix_UB_33      -0.0186896000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_laue_measured_fraction_full 0.997
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_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
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_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11762
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.341
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.243
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour
;
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_exptl_crystal_density_diffrn    1.669
_exptl_crystal_description
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_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         5686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0190P)^2^+0.2043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                4603
_reflns_number_total             5686
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02926_si_001.cif
_cod_data_source_block           20150353
_cod_database_code               1540625
_chemical_oxdiff_formula         C20H20N4O4P1W2
_shelx_estimated_absorpt_t_max   0.550
_shelx_estimated_absorpt_t_min   0.484
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              96064
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'