Triaryl-Like MONO-, BIS-, and TRISKITPHOS Phosphines: Synthesis, Solution NMR Studies, and a Comparison in Gold-Catalyzed Carbon‒Heteroatom Bond Forming 5-exo-dig and 6-endo-dig Cyclizations
Doherty, Simon; Knight, Julian G.; Perry, Daniel O.; Ward, Nicholas A. B.; Bittner, Dror M.; McFarlane, William; Wills, Corinne; Probert, Michael R.; Organometallics 35 (2016) 1265–; doi:10.1021/acs.organomet.6b00146

data_4088516
_publ_section_title
;
 Triaryl-Like MONO-, BIS-, and TRISKITPHOS Phosphines: Synthesis, Solution
 NMR Studies, and a Comparison in Gold-Catalyzed Carbon--Heteroatom Bond
 Forming 5-exo-dig and 6-endo-dig Cyclizations
;
_journal_issue                   9
_journal_name_full               Organometallics
_journal_page_first              1265
_journal_paper_doi               10.1021/acs.organomet.6b00146
_journal_volume                  35
_journal_year                    2016
_chemical_formula_moiety         'C28 H21 Au Cl P, C H Cl3'
_chemical_formula_sum            'C29 H22 Au Cl4 P'
_chemical_formula_weight         740.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.430(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2812(3)
_cell_length_b                   15.2705(3)
_cell_length_c                   16.0309(3)
_cell_measurement_reflns_used    15300
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      28.6097
_cell_measurement_theta_min      2.8951
_cell_volume                     2724.32(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_details
;
  1 omega  -11.00   37.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.1850   77.0000   90.0000 48

  2 omega  -28.00   37.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   89.0000 -166.0000 65

  3 omega  -12.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   38.0000  -30.0000 98

  4 omega  -16.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   38.0000   60.0000 99

  5 omega   -2.00   24.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -38.0000 -180.0000 26

  6 omega  -65.00  -40.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -38.0000    0.0000 25

  7 omega  -30.00   16.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038    0.0000  -30.0000 46
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0365643000
_diffrn_orient_matrix_UB_12      0.0300796000
_diffrn_orient_matrix_UB_13      -0.0179733000
_diffrn_orient_matrix_UB_21      -0.0491405000
_diffrn_orient_matrix_UB_22      0.0294277000
_diffrn_orient_matrix_UB_23      -0.0085106000
_diffrn_orient_matrix_UB_31      0.0175890000
_diffrn_orient_matrix_UB_32      0.0196821000
_diffrn_orient_matrix_UB_33      0.0402012000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28272
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.673
_diffrn_reflns_theta_min         2.901
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.869
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_description       block
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.999
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         6209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0231
_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^)+(0.0200P)^2^+2.3270P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0508
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5472
_reflns_number_total             6209
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00146_si_002.cif
_cod_data_source_block           jgk78
_cod_database_code               4088516
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C28 H21 P Au Cl'
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C10(H10), C29(H29)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28)
;
_shelx_res_checksum              61841
_shelx_hkl_checksum              6572
_olex2_submission_special_instructions 'No special instructions were received'