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_4088517
_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         'C34 H25 Au Cl P, 1(C H Cl3)'
_chemical_formula_sum            'C35 H26 Au Cl4 P'
_chemical_formula_weight         816.29
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.098(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5237(6)
_cell_length_b                   16.5920(7)
_cell_length_c                   15.2157(6)
_cell_measurement_reflns_used    16164
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      29.5501
_cell_measurement_theta_min      3.0044
_cell_volume                     3206.3(2)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (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 0.869
_diffrn_measurement_details
;
  1 omega  -37.00   64.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.7903   38.0000  -30.0000 101

  2 omega  -24.00   45.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       12.6653  -77.0000 -150.0000 69

  3 omega   56.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       12.6653  179.0000  -90.0000 32

  4 omega  -22.00   10.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       12.6653  117.0000  -11.0000 32

  5 omega  -32.00   -6.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       12.6653  -77.0000  120.0000 26

  6 omega   21.00   46.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       12.6653  -77.0000  120.0000 25

  7 omega   74.00  100.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       12.6653  179.0000   90.0000 26

  8 omega  -46.00  -21.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       12.6653  -38.0000  -90.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0453557000
_diffrn_orient_matrix_UB_12      -0.0245312000
_diffrn_orient_matrix_UB_13      -0.0085632000
_diffrn_orient_matrix_UB_21      0.0324709000
_diffrn_orient_matrix_UB_22      -0.0345540000
_diffrn_orient_matrix_UB_23      0.0139912000
_diffrn_orient_matrix_UB_31      0.0023515000
_diffrn_orient_matrix_UB_32      0.0057998000
_diffrn_orient_matrix_UB_33      0.0468460000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27373
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.616
_diffrn_reflns_theta_min         3.010
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.995
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
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    1.691
_exptl_crystal_description       block
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.761
_refine_diff_density_min         -1.713
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         7837
_refine_ls_number_restraints     453
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0442P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0729
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6386
_reflns_number_total             7837
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00146_si_002.cif
_cod_data_source_block           sd297
_cod_database_code               4088517
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.316
_shelx_estimated_absorpt_t_min   0.289
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 Cl1T-C1S \\sim Cl1S-C1S \\sim Cl2T-C1S \\sim Cl2S-C1S \\sim Cl3T-C1S \\sim
Cl3S-C1S
 with sigma of 0.02
 Cl1T-C1T \\sim Cl1S-C1S \\sim Cl1U-C1U \\sim Cl2T-C1T \\sim Cl2S-C1S \\sim
Cl2U-C1U \\sim Cl3U-C1U ~
 Cl3T-C1T \\sim Cl3S-C1S
 with sigma of 0.02
 Cl2U-Cl3U \\sim Cl3T-Cl2T \\sim Cl2U-Cl1U \\sim Cl1U-Cl2T \\sim Cl1U-Cl3U
\\sim Cl3T-Cl1T
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C1S) = Uanis(C1T) = Uanis(C1U)
Uanis(Cl1S) = Uanis(Cl1T) = Uanis(Cl1U) = Uanis(Cl3S) = Uanis(Cl3T) =
Uanis(Cl3U) = Uanis(Cl2S) = Uanis(Cl2T) = Uanis(Cl2U)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: Cl1S(0.45273) Cl3S(0.45273) Cl2S(0.45273) C1S(0.45273)
 H1S(0.45273) Cl1T(0.32111) Cl3T(0.32111) Cl2T(0.32111) C1T(0.32111)
 H1T(0.32111) Cl1U(0.22614) Cl2U(0.22614) Cl3U(0.22614) C1U(0.22614)
 H1U(0.22614)
6.a Ternary CH refined with riding coordinates:
 C2(H2), C9(H9), C1S(H1S), C1T(H1T), C1U(H1U)
6.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34)
;
_shelx_res_checksum              42064
_shelx_hkl_checksum              36978
_olex2_submission_special_instructions 'No special instructions were received'