#------------------------------------------------------------------------------
#$Date: 2024-12-06 18:55:44 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296427 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/26/1572639.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_1572639
loop_
_publ_author_name
'León, Félix'
'García-Rodeja, Yago'
'Mallet-Ladeira, Sonia'
'Miqueu, Karinne'
'Szalóki, György'
'Bourissou, Didier'
_publ_section_title
;
 Catechol/o-benzoquinone exchange at gold(iii).
;
_journal_issue                   40
_journal_name_full               'Chemical science'
_journal_page_first              16651
_journal_page_last               16659
_journal_paper_doi               10.1039/d4sc04374j
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C22 H24 Au O2 P, 0,5(C4 H8 O)'
_chemical_formula_sum            'C24 H28 Au O2.5 P'
_chemical_formula_weight         584.4
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      60
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2024-02-09 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.7586(7)
_cell_length_b                   19.2635(7)
_cell_length_c                   14.1296(5)
_cell_measurement_reflns_used    5501
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.20
_cell_measurement_theta_min      2.78
_cell_volume                     4289.3(3)
_computing_cell_refinement       SAINT
_computing_data_collection       APEX2
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEX II Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            45422
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.761
_diffrn_reflns_theta_min         3.426
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.954
_exptl_absorpt_correction_T_max  0.7476
_exptl_absorpt_correction_T_min  0.7043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.81
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.66
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         5542
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0245
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0154P)²+2.1903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0457
_refine_ls_wR_factor_ref         0.0508
_reflns_Friedel_coverage         0
_reflns_number_gt                4147
_reflns_number_total             5542
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc04374j2.cif
_cod_data_source_block           GS0145-4
_cod_depositor_comments
'Adding full bibliography for 1572639--1572645.cif.'
_cod_original_formula_sum        'C24 H28 Au O2.50 P'
_cod_database_code               1572639
_shelx_shelxl_version_number     2018/3
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2986(2) 0.61750(18) 0.3694(2) 0.0233(7) Uani 1 1 d . . . . .
C2 C 0.2433(2) 0.58964(17) 0.3000(2) 0.0219(7) Uani 1 1 d . . . . .
C3 C 0.2268(2) 0.62663(17) 0.2146(2) 0.0224(7) Uani 1 1 d . . . . .
C4 C 0.1692(2) 0.60193(19) 0.1505(3) 0.0284(8) Uani 1 1 d . . . . .
H4 H 0.157287 0.62773 0.094749 0.034 Uiso 1 1 calc R U . . .
C5 C 0.1273(2) 0.5383(2) 0.1668(3) 0.0325(9) Uani 1 1 d . . . . .
H5 H 0.087077 0.521557 0.122282 0.039 Uiso 1 1 calc R U . . .
C6 C 0.1447(2) 0.50048(18) 0.2471(3) 0.0298(8) Uani 1 1 d . . . . .
H6 H 0.117394 0.45707 0.256534 0.036 Uiso 1 1 calc R U . . .
C7 C 0.2025(2) 0.52516(18) 0.3157(2) 0.0245(7) Uani 1 1 d . . . . .
C8 C 0.2209(2) 0.48878(18) 0.4008(3) 0.0323(9) Uani 1 1 d . . . . .
H8 H 0.194578 0.445299 0.41274 0.039 Uiso 1 1 calc R U . . .
C9 C 0.2758(2) 0.5157(2) 0.4651(3) 0.0351(9) Uani 1 1 d . . . . .
H9 H 0.287904 0.490378 0.521254 0.042 Uiso 1 1 calc R U . . .
C10 C 0.3153(2) 0.58051(19) 0.4500(2) 0.0293(8) Uani 1 1 d . . . . .
H10 H 0.353478 0.598512 0.495879 0.035 Uiso 1 1 calc R U . . .
C11 C 0.2173(2) 0.77726(18) 0.1762(2) 0.0298(8) Uani 1 1 d . . . . .
H11 H 0.187621 0.766049 0.115559 0.036 Uiso 1 1 calc R U . . .
C12 C 0.1509(3) 0.7851(2) 0.2531(3) 0.0504(11) Uani 1 1 d . . . . .
H12A H 0.17849 0.798901 0.312337 0.076 Uiso 1 1 calc R U . . .
H12B H 0.121555 0.740759 0.262212 0.076 Uiso 1 1 calc R U . . .
H12C H 0.109792 0.820715 0.234407 0.076 Uiso 1 1 calc R U . . .
C13 C 0.2676(3) 0.8438(2) 0.1621(3) 0.0534(13) Uani 1 1 d . . . . .
H13A H 0.228512 0.882205 0.148924 0.08 Uiso 1 1 calc R U . . .
H13B H 0.306633 0.8381 0.108661 0.08 Uiso 1 1 calc R U . . .
H13C H 0.300069 0.854091 0.219563 0.08 Uiso 1 1 calc R U . . .
C14 C 0.3666(2) 0.6967(2) 0.1116(2) 0.0315(9) Uani 1 1 d . . . . .
H14 H 0.403433 0.738954 0.113496 0.038 Uiso 1 1 calc R U . . .
C15 C 0.4228(2) 0.6340(3) 0.1290(3) 0.0441(11) Uani 1 1 d . . . . .
H15A H 0.388504 0.591615 0.125622 0.066 Uiso 1 1 calc R U . . .
H15B H 0.448673 0.63762 0.191886 0.066 Uiso 1 1 calc R U . . .
H15C H 0.467451 0.632244 0.08082 0.066 Uiso 1 1 calc R U . . .
C16 C 0.3250(3) 0.6937(3) 0.0136(3) 0.0458(11) Uani 1 1 d . . . . .
H16A H 0.369066 0.689835 -0.035049 0.069 Uiso 1 1 calc R U . . .
H16B H 0.291922 0.736082 0.003031 0.069 Uiso 1 1 calc R U . . .
H16C H 0.287398 0.653254 0.010169 0.069 Uiso 1 1 calc R U . . .
C17 C 0.4472(2) 0.82382(18) 0.4160(2) 0.0244(7) Uani 1 1 d . . . . .
C18 C 0.4930(2) 0.8846(2) 0.4257(3) 0.0349(9) Uani 1 1 d . . . . .
H18 H 0.492608 0.918013 0.376242 0.042 Uiso 1 1 calc R U . . .
C19 C 0.5397(2) 0.8972(2) 0.5076(3) 0.0388(9) Uani 1 1 d . . . . .
H19 H 0.570879 0.93919 0.513813 0.047 Uiso 1 1 calc R U . . .
C20 C 0.5409(2) 0.8491(2) 0.5795(3) 0.0378(9) Uani 1 1 d . . . . .
H20 H 0.573005 0.857934 0.635079 0.045 Uiso 1 1 calc R U . . .
C21 C 0.4954(2) 0.7879(2) 0.5712(2) 0.0304(8) Uani 1 1 d . . . . .
H21 H 0.496272 0.754992 0.621213 0.037 Uiso 1 1 calc R U . . .
C22 C 0.4483(2) 0.77449(17) 0.4894(2) 0.0243(7) Uani 1 1 d . . . . .
C24 C 0.5113(8) 0.4498(6) 0.3073(8) 0.060(2) Uani 0.5 1 d D U P A -1
H24A H 0.516627 0.399952 0.32314 0.072 Uiso 0.5 1 calc R U P A -1
H24B H 0.527646 0.478003 0.362964 0.072 Uiso 0.5 1 calc R U P A -1
C23 C 0.4232(13) 0.467(2) 0.2743(17) 0.060(3) Uani 0.5 1 d D U P A -1
H23A H 0.380945 0.438134 0.307748 0.073 Uiso 0.5 1 calc R U P A -1
H23B H 0.410301 0.51661 0.287092 0.073 Uiso 0.5 1 calc R U P A -1
O3 O 0.4206(5) 0.4539(4) 0.1755(5) 0.0642(18) Uani 0.5 1 d D U P A -1
C26 C 0.5058(7) 0.4459(7) 0.1429(8) 0.065(2) Uani 0.5 1 d D U P A -1
H26A H 0.515402 0.474833 0.08595 0.078 Uiso 0.5 1 calc R U P A -1
H26B H 0.516925 0.396828 0.126188 0.078 Uiso 0.5 1 calc R U P A -1
C25 C 0.5637(13) 0.468(2) 0.2214(17) 0.061(3) Uani 0.5 1 d D U P A -1
H25A H 0.575397 0.518904 0.218535 0.073 Uiso 0.5 1 calc R U P A -1
H25B H 0.618019 0.442639 0.220155 0.073 Uiso 0.5 1 calc R U P A -1
O1 O 0.40109(16) 0.80953(13) 0.33709(16) 0.0316(6) Uani 1 1 d . . . . .
O2 O 0.40372(15) 0.71477(13) 0.47919(15) 0.0260(5) Uani 1 1 d . . . . .
P1 P 0.28726(6) 0.70522(5) 0.20545(6) 0.02246(18) Uani 1 1 d . . . . .
Au1 Au 0.34909(2) 0.71286(2) 0.34953(2) 0.02143(4) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
_geom_angle_publ_flag
C10 C1 C2 119.8(3) . . ?
C10 C1 Au1 120.9(3) . . ?
C2 C1 Au1 119.4(2) . . ?
C7 C2 C1 120.2(3) . . ?
C7 C2 C3 119.2(3) . . ?
C1 C2 C3 120.6(3) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 P1 126.7(3) . . ?
C2 C3 P1 112.7(2) . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.1(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C2 118.8(3) . . ?
C6 C7 C8 123.1(3) . . ?
C2 C7 C8 118.1(3) . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.1(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C1 C10 C9 120.1(3) . . ?
C1 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C13 111.7(4) . . ?
C12 C11 P1 109.4(3) . . ?
C13 C11 P1 110.9(3) . . ?
C12 C11 H11 108.2 . . ?
C13 C11 H11 108.2 . . ?
P1 C11 H11 108.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C16 111.5(3) . . ?
C15 C14 P1 110.6(3) . . ?
C16 C14 P1 111.5(3) . . ?
C15 C14 H14 107.7 . . ?
C16 C14 H14 107.7 . . ?
P1 C14 H14 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 C18 122.2(3) . . ?
O1 C17 C22 118.4(3) . . ?
C18 C17 C22 119.4(3) . . ?
C17 C18 C19 120.4(4) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.2(4) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.3(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
O2 C22 C21 121.4(3) . . ?
O2 C22 C17 119.2(3) . . ?
C21 C22 C17 119.4(3) . . ?
C23 C24 C25 101.7(11) . . ?
C23 C24 H24A 111.4 . . ?
C25 C24 H24A 111.4 . . ?
C23 C24 H24B 111.4 . . ?
C25 C24 H24B 111.4 . . ?
H24A C24 H24B 109.3 . . ?
O3 C23 C24 106.9(15) . . ?
O3 C23 H23A 110.3 . . ?
C24 C23 H23A 110.3 . . ?
O3 C23 H23B 110.3 . . ?
C24 C23 H23B 110.3 . . ?
H23A C23 H23B 108.6 . . ?
C23 O3 C26 108.0(12) . . ?
O3 C26 C25 107.6(14) . . ?
O3 C26 H26A 110.2 . . ?
C25 C26 H26A 110.2 . . ?
O3 C26 H26B 110.2 . . ?
C25 C26 H26B 110.2 . . ?
H26A C26 H26B 108.5 . . ?
C26 C25 C24 101.1(13) . . ?
C26 C25 H25A 111.5 . . ?
C24 C25 H25A 111.5 . . ?
C26 C25 H25B 111.6 . . ?
C24 C25 H25B 111.6 . . ?
H25A C25 H25B 109.4 . . ?
C17 O1 Au1 109.2(2) . . ?
C22 O2 Au1 109.42(19) . . ?
C3 P1 C11 109.75(16) . . ?
C3 P1 C14 109.88(16) . . ?
C11 P1 C14 108.51(17) . . ?
C3 P1 Au1 102.63(11) . . ?
C11 P1 Au1 114.56(12) . . ?
C14 P1 Au1 111.35(12) . . ?
C1 Au1 O2 93.34(11) . . ?
C1 Au1 O1 176.94(11) . . ?
O2 Au1 O1 83.72(9) . . ?
C1 Au1 P1 84.05(9) . . ?
O2 Au1 P1 177.28(7) . . ?
O1 Au1 P1 98.90(7) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C10 1.369(4) . ?
C1 C2 1.417(5) . ?
C1 Au1 2.021(3) . ?
C2 C7 1.416(5) . ?
C2 C3 1.425(4) . ?
C3 C4 1.368(5) . ?
C3 P1 1.794(3) . ?
C4 C5 1.410(5) . ?
C4 H4 0.95 . ?
C5 C6 1.376(5) . ?
C5 H5 0.95 . ?
C6 C7 1.412(5) . ?
C6 H6 0.95 . ?
C7 C8 1.422(5) . ?
C8 C9 1.357(5) . ?
C8 H8 0.95 . ?
C9 C10 1.412(5) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 C12 1.515(5) . ?
C11 C13 1.521(5) . ?
C11 P1 1.820(4) . ?
C11 H11 1 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 C15 1.519(6) . ?
C14 C16 1.532(5) . ?
C14 P1 1.830(4) . ?
C14 H14 1 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 O1 1.358(4) . ?
C17 C18 1.383(5) . ?
C17 C22 1.408(5) . ?
C18 C19 1.393(5) . ?
C18 H18 0.95 . ?
C19 C20 1.375(5) . ?
C19 H19 0.95 . ?
C20 C21 1.384(5) . ?
C20 H20 0.95 . ?
C21 C22 1.397(5) . ?
C21 H21 0.95 . ?
C22 O2 1.356(4) . ?
C24 C23 1.502(15) . ?
C24 C25 1.51(3) . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C23 O3 1.42(2) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
O3 C26 1.428(13) . ?
C26 C25 1.500(15) . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?
C25 H25A 0.99 . ?
C25 H25B 0.99 . ?
O1 Au1 2.042(2) . ?
O2 Au1 2.025(2) . ?
P1 Au1 2.2617(8) . ?
