#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:01:10 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301838 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/99/4329900.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4329900
loop_
_publ_author_name
'David V. Partyka'
'Matthias Zeller'
'Allen D. Hunter'
'Thomas G. Gray'
_publ_section_title
;
 Arylgold(I) Complexes from Base-Assisted Transmetalation: Structures, NMR
 Properties, and Density-Functional Theory Calculations
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8394
_journal_page_last               8401
_journal_paper_doi               10.1021/ic3009464
_journal_volume                  51
_journal_year                    2012
_chemical_formula_moiety         'C20 H36 Au O2 P, 0.5(C6 H6)'
_chemical_formula_sum            'C23 H39 Au O2 P'
_chemical_formula_weight         575.48
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.093(4)
_cell_angle_beta                 100.704(4)
_cell_angle_gamma                96.207(4)
_cell_formula_units_Z            2
_cell_length_a                   9.074(2)
_cell_length_b                   10.612(2)
_cell_length_c                   12.973(3)
_cell_measurement_reflns_used    5182
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.48
_cell_measurement_theta_min      3.04
_cell_volume                     1155.5(4)
_computing_cell_refinement       'SAINT+ 6.45 (Bruker, 2003)'
_computing_data_collection       'SMART 5.630 (Bruker, 1997-2002)'
_computing_data_reduction        'SAINT+ 6.45'
_computing_molecular_graphics    'SHELXTL 6.14'
_computing_publication_material  'SHELXTL 6.14'
_computing_structure_refinement  'SHELXTL 6.14'
_computing_structure_solution    'SHELXTL 6.14 (Bruker, 2000-2003)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11826
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.69
_diffrn_standards_decay_%        none
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.450
_exptl_absorpt_correction_T_max  0.525
_exptl_absorpt_correction_T_min  0.231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS in SAINT+ (Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_description       rod
_exptl_crystal_F_000             574
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         5.980
_refine_diff_density_min         -1.256
_refine_diff_density_rms         0.287
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         5683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0763P)²+2.7048P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                5218
_reflns_number_total             5683
_reflns_threshold_expression     >I>2σ(I)
_cod_data_source_file            ic3009464_si_002_6.cif
_cod_data_source_block           Cpd_8_06mz313m
_cod_database_code               4329900
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Au2 Au -0.12717(2) 0.24582(2) -0.034508(16) 0.01902(9) Uani 1 1 d .
C1 C -0.3309(7) 0.1241(7) -0.2513(5) 0.0262(12) Uani 1 1 d .
C2 C -0.4245(11) 0.1366(10) -0.3565(7) 0.050(2) Uani 1 1 d .
H2A H -0.3621 0.1298 -0.4113 0.075 Uiso 1 1 calc R
H2B H -0.4584 0.2235 -0.3398 0.075 Uiso 1 1 calc R
H2C H -0.5134 0.0647 -0.3862 0.075 Uiso 1 1 calc R
C3 C -0.0429(6) 0.1436(6) 0.1895(5) 0.0189(10) Uani 1 1 d .
H3 H -0.0219 0.0615 0.1366 0.023 Uiso 1 1 calc R
C4 C 0.0521(7) 0.1568(6) 0.3036(5) 0.0214(11) Uani 1 1 d .
H4A H 0.0381 0.2388 0.3590 0.026 Uiso 1 1 calc R
H4B H 0.1613 0.1645 0.3020 0.026 Uiso 1 1 calc R
C5 C 0.0034(8) 0.0340(6) 0.3369(5) 0.0244(12) Uani 1 1 d .
H5A H 0.0234 -0.0472 0.2839 0.029 Uiso 1 1 calc R
H5B H 0.0646 0.0443 0.4114 0.029 Uiso 1 1 calc R
C6 C -0.1646(8) 0.0169(6) 0.3382(5) 0.0257(12) Uani 1 1 d .
H6A H -0.1841 0.0960 0.3938 0.031 Uiso 1 1 calc R
H6B H -0.1929 -0.0630 0.3595 0.031 Uiso 1 1 calc R
C7 C -0.2622(8) 0.0009(7) 0.2234(6) 0.0277(13) Uani 1 1 d .
H7A H -0.2507 -0.0834 0.1693 0.033 Uiso 1 1 calc R
H7B H -0.3708 -0.0048 0.2266 0.033 Uiso 1 1 calc R
C8 C -0.2146(7) 0.1191(7) 0.1848(6) 0.0250(12) Uani 1 1 d .
H8A H -0.2418 0.2008 0.2321 0.030 Uiso 1 1 calc R
H8B H -0.2718 0.1016 0.1078 0.030 Uiso 1 1 calc R
C9 C -0.0317(7) 0.4337(6) 0.2363(5) 0.0222(11) Uani 1 1 d .
H9 H -0.1181 0.4014 0.2652 0.027 Uiso 1 1 calc R
C10 C 0.0972(7) 0.5041(6) 0.3385(5) 0.0214(11) Uani 1 1 d .
H10A H 0.1296 0.4384 0.3748 0.026 Uiso 1 1 calc R
H10B H 0.1857 0.5418 0.3157 0.026 Uiso 1 1 calc R
C11 C 0.0455(9) 0.6152(6) 0.4196(5) 0.0296(14) Uani 1 1 d .
H11A H 0.1314 0.6613 0.4840 0.036 Uiso 1 1 calc R
H11B H -0.0374 0.5762 0.4469 0.036 Uiso 1 1 calc R
C12 C -0.0110(9) 0.7166(7) 0.3660(6) 0.0312(14) Uani 1 1 d .
H12A H -0.0482 0.7856 0.4200 0.037 Uiso 1 1 calc R
H12B H 0.0744 0.7618 0.3450 0.037 Uiso 1 1 calc R
C13 C -0.1381(8) 0.6488(6) 0.2641(6) 0.0276(13) Uani 1 1 d .
H13A H -0.1674 0.7153 0.2278 0.033 Uiso 1 1 calc R
H13B H -0.2282 0.6134 0.2865 0.033 Uiso 1 1 calc R
C14 C -0.0898(8) 0.5335(6) 0.1813(5) 0.0247(12) Uani 1 1 d .
H14A H -0.1778 0.4868 0.1187 0.030 Uiso 1 1 calc R
H14B H -0.0085 0.5703 0.1514 0.030 Uiso 1 1 calc R
C15 C 0.2106(6) 0.3019(6) 0.1449(5) 0.0174(10) Uani 1 1 d .
H15 H 0.2651 0.3233 0.2240 0.021 Uiso 1 1 calc R
C16 C 0.2496(7) 0.1681(5) 0.0761(6) 0.0238(12) Uani 1 1 d .
H16A H 0.2210 0.0960 0.1064 0.029 Uiso 1 1 calc R
H16B H 0.1922 0.1420 -0.0020 0.029 Uiso 1 1 calc R
C17 C 0.4195(7) 0.1882(7) 0.0821(6) 0.0287(13) Uani 1 1 d .
H17A H 0.4743 0.2047 0.1596 0.034 Uiso 1 1 calc R
H17B H 0.4443 0.1044 0.0359 0.034 Uiso 1 1 calc R
C18 C 0.4777(7) 0.3024(7) 0.0442(6) 0.0282(13) Uani 1 1 d .
H18A H 0.4329 0.2825 -0.0356 0.034 Uiso 1 1 calc R
H18B H 0.5898 0.3127 0.0550 0.034 Uiso 1 1 calc R
C19 C 0.4348(8) 0.4318(6) 0.1104(6) 0.0281(13) Uani 1 1 d .
H19A H 0.4668 0.5046 0.0817 0.034 Uiso 1 1 calc R
H19B H 0.4896 0.4568 0.1890 0.034 Uiso 1 1 calc R
C20 C 0.2638(8) 0.4171(6) 0.1032(5) 0.0248(12) Uani 1 1 d .
H20A H 0.2088 0.3986 0.0255 0.030 Uiso 1 1 calc R
H20B H 0.2398 0.5018 0.1487 0.030 Uiso 1 1 calc R
C21 C 0.4878(11) 0.3630(11) 0.4451(8) 0.052(2) Uani 1 1 d .
H21 H 0.4797 0.2701 0.4079 0.062 Uiso 1 1 calc R
C22 C 0.4053(11) 0.4068(13) 0.5224(9) 0.057(3) Uani 1 1 d .
H22 H 0.3391 0.3433 0.5387 0.069 Uiso 1 1 calc R
C23 C 0.4160(11) 0.5431(12) 0.5781(7) 0.052(2) Uani 1 1 d .
H23 H 0.3576 0.5716 0.6316 0.062 Uiso 1 1 calc R
O1 O -0.2450(6) 0.2333(5) -0.1893(4) 0.0278(10) Uani 1 1 d .
O2 O -0.3411(7) 0.0188(5) -0.2319(5) 0.0408(12) Uani 1 1 d .
P1 P 0.00572(17) 0.28292(14) 0.13706(12) 0.0171(3) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 Au2 P1 173.88(13) . .
O2 C1 O1 125.8(7) . .
O2 C1 C2 121.3(7) . .
O1 C1 C2 112.9(6) . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C4 C3 C8 111.7(5) . .
C4 C3 P1 115.0(4) . .
C8 C3 P1 110.3(4) . .
C4 C3 H3 106.4 . .
C8 C3 H3 106.4 . .
P1 C3 H3 106.4 . .
C3 C4 C5 110.1(5) . .
C3 C4 H4A 109.6 . .
C5 C4 H4A 109.6 . .
C3 C4 H4B 109.6 . .
C5 C4 H4B 109.6 . .
H4A C4 H4B 108.2 . .
C6 C5 C4 111.3(5) . .
C6 C5 H5A 109.4 . .
C4 C5 H5A 109.4 . .
C6 C5 H5B 109.4 . .
C4 C5 H5B 109.4 . .
H5A C5 H5B 108.0 . .
C5 C6 C7 110.4(5) . .
C5 C6 H6A 109.6 . .
C7 C6 H6A 109.6 . .
C5 C6 H6B 109.6 . .
C7 C6 H6B 109.6 . .
H6A C6 H6B 108.1 . .
C8 C7 C6 110.9(5) . .
C8 C7 H7A 109.5 . .
C6 C7 H7A 109.5 . .
C8 C7 H7B 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 108.0 . .
C7 C8 C3 112.5(5) . .
C7 C8 H8A 109.1 . .
C3 C8 H8A 109.1 . .
C7 C8 H8B 109.1 . .
C3 C8 H8B 109.1 . .
H8A C8 H8B 107.8 . .
C14 C9 C10 110.9(5) . .
C14 C9 P1 113.0(4) . .
C10 C9 P1 115.8(4) . .
C14 C9 H9 105.3 . .
C10 C9 H9 105.3 . .
P1 C9 H9 105.3 . .
C11 C10 C9 110.6(5) . .
C11 C10 H10A 109.5 . .
C9 C10 H10A 109.5 . .
C11 C10 H10B 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 108.1 . .
C10 C11 C12 111.4(5) . .
C10 C11 H11A 109.3 . .
C12 C11 H11A 109.3 . .
C10 C11 H11B 109.3 . .
C12 C11 H11B 109.3 . .
H11A C11 H11B 108.0 . .
C13 C12 C11 110.9(5) . .
C13 C12 H12A 109.4 . .
C11 C12 H12A 109.4 . .
C13 C12 H12B 109.4 . .
C11 C12 H12B 109.4 . .
H12A C12 H12B 108.0 . .
C12 C13 C14 111.5(5) . .
C12 C13 H13A 109.3 . .
C14 C13 H13A 109.3 . .
C12 C13 H13B 109.3 . .
C14 C13 H13B 109.3 . .
H13A C13 H13B 108.0 . .
C9 C14 C13 111.2(5) . .
C9 C14 H14A 109.4 . .
C13 C14 H14A 109.4 . .
C9 C14 H14B 109.4 . .
C13 C14 H14B 109.4 . .
H14A C14 H14B 108.0 . .
C20 C15 C16 110.6(5) . .
C20 C15 P1 110.9(4) . .
C16 C15 P1 109.6(4) . .
C20 C15 H15 108.5 . .
C16 C15 H15 108.5 . .
P1 C15 H15 108.5 . .
C17 C16 C15 108.3(5) . .
C17 C16 H16A 110.0 . .
C15 C16 H16A 110.0 . .
C17 C16 H16B 110.0 . .
C15 C16 H16B 110.0 . .
H16A C16 H16B 108.4 . .
C18 C17 C16 114.6(5) . .
C18 C17 H17A 108.6 . .
C16 C17 H17A 108.6 . .
C18 C17 H17B 108.6 . .
C16 C17 H17B 108.6 . .
H17A C17 H17B 107.6 . .
C17 C18 C19 109.8(5) . .
C17 C18 H18A 109.7 . .
C19 C18 H18A 109.7 . .
C17 C18 H18B 109.7 . .
C19 C18 H18B 109.7 . .
H18A C18 H18B 108.2 . .
C18 C19 C20 111.5(5) . .
C18 C19 H19A 109.3 . .
C20 C19 H19A 109.3 . .
C18 C19 H19B 109.3 . .
C20 C19 H19B 109.3 . .
H19A C19 H19B 108.0 . .
C19 C20 C15 110.2(5) . .
C19 C20 H20A 109.6 . .
C15 C20 H20A 109.6 . .
C19 C20 H20B 109.6 . .
C15 C20 H20B 109.6 . .
H20A C20 H20B 108.1 . .
C22 C21 C23 118.8(10) . 2_666
C22 C21 H21 120.6 . .
C23 C21 H21 120.6 2_666 .
C21 C22 C23 121.4(10) . .
C21 C22 H22 119.3 . .
C23 C22 H22 119.3 . .
C21 C23 C22 119.8(9) 2_666 .
C21 C23 H23 120.1 2_666 .
C22 C23 H23 120.1 . .
C1 O1 Au2 119.6(4) . .
C15 P1 C9 108.2(3) . .
C15 P1 C3 106.6(3) . .
C9 P1 C3 105.9(3) . .
C15 P1 Au2 111.73(19) . .
C9 P1 Au2 112.2(2) . .
C3 P1 Au2 111.89(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Au2 O1 2.052(4) .
Au2 P1 2.2245(15) .
C1 O2 1.213(9) .
C1 O1 1.273(8) .
C1 C2 1.517(10) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 C4 1.527(8) .
C3 C8 1.538(8) .
C3 P1 1.846(6) .
C3 H3 1.0000 .
C4 C5 1.535(8) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.519(9) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.536(10) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.530(9) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C14 1.527(8) .
C9 C10 1.529(8) .
C9 P1 1.844(6) .
C9 H9 1.0000 .
C10 C11 1.514(9) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.527(9) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.513(10) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.536(9) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C20 1.542(8) .
C15 C16 1.555(8) .
C15 P1 1.829(6) .
C15 H15 1.0000 .
C16 C17 1.518(9) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.516(9) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.523(9) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.526(9) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 C22 1.365(15) .
C21 C23 1.389(15) 2_666
C21 H21 0.9500 .
C22 C23 1.397(16) .
C22 H22 0.9500 .
C23 C21 1.389(15) 2_666
C23 H23 0.9500 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C8 C3 C4 C5 54.4(6) . .
P1 C3 C4 C5 -178.8(4) . .
C3 C4 C5 C6 -58.2(7) . .
C4 C5 C6 C7 59.0(7) . .
C5 C6 C7 C8 -55.8(7) . .
C6 C7 C8 C3 53.0(7) . .
C4 C3 C8 C7 -52.9(7) . .
P1 C3 C8 C7 177.8(5) . .
C14 C9 C10 C11 56.5(7) . .
P1 C9 C10 C11 -173.0(4) . .
C9 C10 C11 C12 -57.2(7) . .
C10 C11 C12 C13 56.6(8) . .
C11 C12 C13 C14 -54.8(8) . .
C10 C9 C14 C13 -55.1(7) . .
P1 C9 C14 C13 173.0(4) . .
C12 C13 C14 C9 54.6(7) . .
C20 C15 C16 C17 56.1(7) . .
P1 C15 C16 C17 178.7(4) . .
C15 C16 C17 C18 -56.1(8) . .
C16 C17 C18 C19 55.8(8) . .
C17 C18 C19 C20 -55.1(7) . .
C18 C19 C20 C15 57.6(7) . .
C16 C15 C20 C19 -58.2(6) . .
P1 C15 C20 C19 179.9(4) . .
C23 C21 C22 C23 -0.1(15) 2_666 .
C21 C22 C23 C21 0.1(15) . 2_666
O2 C1 O1 Au2 -7.1(10) . .
C2 C1 O1 Au2 172.8(5) . .
C20 C15 P1 C9 -66.2(5) . .
C16 C15 P1 C9 171.3(4) . .
C20 C15 P1 C3 -179.7(4) . .
C16 C15 P1 C3 57.8(5) . .
C20 C15 P1 Au2 57.8(4) . .
C16 C15 P1 Au2 -64.7(4) . .
C14 C9 P1 C15 100.2(5) . .
C10 C9 P1 C15 -29.4(5) . .
C14 C9 P1 C3 -145.8(4) . .
C10 C9 P1 C3 84.6(5) . .
C14 C9 P1 Au2 -23.5(5) . .
C10 C9 P1 Au2 -153.1(4) . .
C4 C3 P1 C15 53.2(5) . .
C8 C3 P1 C15 -179.3(4) . .
C4 C3 P1 C9 -61.9(5) . .
C8 C3 P1 C9 65.6(5) . .
C4 C3 P1 Au2 175.6(4) . .
C8 C3 P1 Au2 -56.9(4) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168337775
