#------------------------------------------------------------------------------
#$Date: 2024-12-06 18:55:44 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296427 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/26/1572641.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_1572641
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 H22 Au Cl2 O2 P'
_chemical_formula_sum            'C22 H22 Au Cl2 O2 P'
_chemical_formula_weight         617.24
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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     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                 98.291(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7611(7)
_cell_length_b                   14.4997(9)
_cell_length_c                   13.7734(8)
_cell_measurement_reflns_used    9410
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      42.08
_cell_measurement_theta_min      3.31
_cell_volume                     2126.6(2)
_computing_cell_refinement       'APEX2 and 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, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  triumph
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            145612
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         42.16
_diffrn_reflns_theta_min         2.653
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.26
_exptl_absorpt_correction_T_max  0.7483
_exptl_absorpt_correction_T_min  0.5189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.928
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.237
_refine_diff_density_min         -1.119
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         14871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0202
_refine_ls_R_factor_gt           0.0153
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0155P)²+0.4630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0359
_refine_ls_wR_factor_ref         0.0373
_reflns_Friedel_coverage         0
_reflns_number_gt                13124
_reflns_number_total             14871
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc04374j2.cif
_cod_data_source_block           GS0383-1
_cod_depositor_comments
'Adding full bibliography for 1572639--1572645.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1572641
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Au1 Au 0.64650(2) 0.64345(2) 0.42272(2) 0.019310(10) Uani 1 1 d . . . . .
P1 P 0.66064(2) 0.77092(2) 0.51645(2) 0.01918(3) Uani 1 1 d . . . . .
Cl2 Cl 0.89724(4) 0.34141(3) 0.12941(3) 0.04687(8) Uani 1 1 d . . . . .
Cl1 Cl 1.10737(3) 0.49881(2) 0.17247(3) 0.04121(7) Uani 1 1 d . . . . .
O2 O 0.63355(7) 0.53073(5) 0.33349(6) 0.02534(12) Uani 1 1 d . . . . .
C1 C 0.47090(9) 0.63590(6) 0.45656(7) 0.02170(13) Uani 1 1 d . . . . .
O1 O 0.82361(8) 0.65263(5) 0.38706(7) 0.02770(14) Uani 1 1 d . . . . .
C22 C 0.74460(9) 0.51793(6) 0.30121(7) 0.02246(14) Uani 1 1 d . . . . .
C9 C 0.26435(10) 0.56691(8) 0.44106(10) 0.0323(2) Uani 1 1 d . . . . .
H9 H 0.206685 0.522255 0.410905 0.039 Uiso 1 1 calc R U . . .
C2 C 0.43288(8) 0.69988(6) 0.52507(7) 0.02147(13) Uani 1 1 d . . . . .
C7 C 0.31103(9) 0.69435(7) 0.55280(8) 0.02640(16) Uani 1 1 d . . . . .
C10 C 0.38745(10) 0.56976(7) 0.41606(8) 0.02729(16) Uani 1 1 d . . . . .
H10 H 0.412396 0.525988 0.371315 0.033 Uiso 1 1 calc R U . . .
C21 C 0.76545(10) 0.44304(7) 0.24245(7) 0.02663(16) Uani 1 1 d . . . . .
H21 H 0.702295 0.397315 0.227836 0.032 Uiso 1 1 calc R U . . .
C20 C 0.87862(11) 0.43477(7) 0.20490(7) 0.02845(18) Uani 1 1 d . . . . .
C17 C 0.84216(9) 0.58257(6) 0.32722(7) 0.02242(14) Uani 1 1 d . . . . .
C15 C 0.68512(14) 0.96110(8) 0.49842(10) 0.0369(2) Uani 1 1 d . . . . .
H15A H 0.683708 1.014091 0.45411 0.055 Uiso 1 1 calc R U . . .
H15B H 0.766102 0.958874 0.54126 0.055 Uiso 1 1 calc R U . . .
H15C H 0.617347 0.967258 0.538488 0.055 Uiso 1 1 calc R U . . .
C8 C 0.22663(10) 0.62687(9) 0.50749(10) 0.0323(2) Uani 1 1 d . . . . .
H8 H 0.143723 0.623336 0.523349 0.039 Uiso 1 1 calc R U . . .
C14 C 0.66669(11) 0.87227(7) 0.43819(8) 0.02610(16) Uani 1 1 d . . . . .
H14 H 0.740586 0.865077 0.402365 0.031 Uiso 1 1 calc R U . . .
C5 C 0.36541(11) 0.81950(9) 0.66890(9) 0.0321(2) Uani 1 1 d . . . . .
H5 H 0.343303 0.858562 0.719075 0.039 Uiso 1 1 calc R U . . .
C19 C 0.97114(10) 0.50091(7) 0.22620(8) 0.02765(17) Uani 1 1 d . . . . .
C18 C 0.95421(9) 0.57412(7) 0.28858(7) 0.02554(15) Uani 1 1 d . . . . .
H18 H 1.019155 0.61825 0.304726 0.031 Uiso 1 1 calc R U . . .
C6 C 0.28072(10) 0.75605(9) 0.62588(9) 0.0323(2) Uani 1 1 d . . . . .
H6 H 0.199665 0.75322 0.645397 0.039 Uiso 1 1 calc R U . . .
C16 C 0.54889(14) 0.87668(9) 0.36193(10) 0.0369(2) Uani 1 1 d . . . . .
H16A H 0.475027 0.88518 0.395096 0.055 Uiso 1 1 calc R U . . .
H16B H 0.540368 0.819101 0.324296 0.055 Uiso 1 1 calc R U . . .
H16C H 0.555653 0.928595 0.317429 0.055 Uiso 1 1 calc R U . . .
C11 C 0.79237(9) 0.77483(8) 0.61455(8) 0.02803(17) Uani 1 1 d . . . . .
H11 H 0.781144 0.83047 0.655302 0.034 Uiso 1 1 calc R U . . .
C4 C 0.48533(10) 0.82750(8) 0.63946(8) 0.02728(17) Uani 1 1 d . . . . .
H4 H 0.543407 0.872367 0.668598 0.033 Uiso 1 1 calc R U . . .
C3 C 0.51688(8) 0.76913(6) 0.56770(7) 0.02188(13) Uani 1 1 d . . . . .
C12 C 0.91711(11) 0.78577(12) 0.57523(12) 0.0452(3) Uani 1 1 d . . . . .
H12A H 0.98595 0.787035 0.630184 0.068 Uiso 1 1 calc R U . . .
H12B H 0.916519 0.843534 0.538213 0.068 Uiso 1 1 calc R U . . .
H12C H 0.928942 0.733777 0.532032 0.068 Uiso 1 1 calc R U . . .
C13 C 0.79154(17) 0.69075(11) 0.68064(11) 0.0477(3) Uani 1 1 d . . . . .
H13A H 0.817078 0.636173 0.646476 0.072 Uiso 1 1 calc R U . . .
H13B H 0.706746 0.681421 0.696934 0.072 Uiso 1 1 calc R U . . .
H13C H 0.85028 0.700518 0.741061 0.072 Uiso 1 1 calc R U . . .
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'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
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
C1 Au1 O2 96.38(3) . . ?
C1 Au1 O1 179.17(4) . . ?
O2 Au1 O1 83.81(3) . . ?
C1 Au1 P1 84.25(3) . . ?
O2 Au1 P1 177.99(2) . . ?
O1 Au1 P1 95.54(2) . . ?
C3 P1 C11 109.50(5) . . ?
C3 P1 C14 110.49(5) . . ?
C11 P1 C14 108.88(5) . . ?
C3 P1 Au1 102.93(3) . . ?
C11 P1 Au1 115.78(4) . . ?
C14 P1 Au1 109.12(4) . . ?
C22 O2 Au1 108.84(6) . . ?
C10 C1 C2 119.30(9) . . ?
C10 C1 Au1 121.57(7) . . ?
C2 C1 Au1 119.12(7) . . ?
C17 O1 Au1 109.00(6) . . ?
O2 C22 C21 121.65(9) . . ?
O2 C22 C17 119.13(8) . . ?
C21 C22 C17 119.23(9) . . ?
C8 C9 C10 121.53(10) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C7 C2 C3 119.08(9) . . ?
C7 C2 C1 120.40(9) . . ?
C3 C2 C1 120.51(8) . . ?
C8 C7 C6 123.32(10) . . ?
C8 C7 C2 118.59(10) . . ?
C6 C7 C2 118.08(10) . . ?
C1 C10 C9 120.03(10) . . ?
C1 C10 H10 120 . . ?
C9 C10 H10 120 . . ?
C22 C21 C20 120.35(10) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C19 C20 C21 120.12(9) . . ?
C19 C20 Cl2 121.74(8) . . ?
C21 C20 Cl2 118.12(9) . . ?
O1 C17 C18 121.03(9) . . ?
O1 C17 C22 119.13(8) . . ?
C18 C17 C22 119.82(8) . . ?
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 . . ?
C9 C8 C7 120.07(10) . . ?
C9 C8 H8 120 . . ?
C7 C8 H8 120 . . ?
C16 C14 C15 111.58(10) . . ?
C16 C14 P1 110.03(8) . . ?
C15 C14 P1 111.71(8) . . ?
C16 C14 H14 107.8 . . ?
C15 C14 H14 107.8 . . ?
P1 C14 H14 107.8 . . ?
C6 C5 C4 120.67(10) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C20 C19 C18 120.31(9) . . ?
C20 C19 Cl1 121.59(8) . . ?
C18 C19 Cl1 118.03(9) . . ?
C17 C18 C19 120.01(10) . . ?
C17 C18 H18 120 . . ?
C19 C18 H18 120 . . ?
C5 C6 C7 121.61(9) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
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 . . ?
C13 C11 C12 112.13(12) . . ?
C13 C11 P1 110.44(9) . . ?
C12 C11 P1 111.83(8) . . ?
C13 C11 H11 107.4 . . ?
C12 C11 H11 107.4 . . ?
P1 C11 H11 107.4 . . ?
C3 C4 C5 118.98(10) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C4 C3 C2 121.46(9) . . ?
C4 C3 P1 126.09(8) . . ?
C2 C3 P1 112.44(6) . . ?
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 . . ?
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
Au1 C1 2.0134(9) . ?
Au1 O2 2.0377(7) . ?
Au1 O1 2.0399(8) . ?
Au1 P1 2.2469(2) . ?
P1 C3 1.7908(9) . ?
P1 C11 1.8128(10) . ?
P1 C14 1.8292(10) . ?
Cl2 C20 1.7360(10) . ?
Cl1 C19 1.7351(10) . ?
O2 C22 1.3466(12) . ?
C1 C10 1.3758(14) . ?
C1 C2 1.4247(13) . ?
O1 C17 1.3411(11) . ?
C22 C21 1.3917(13) . ?
C22 C17 1.4144(13) . ?
C9 C8 1.3656(19) . ?
C9 C10 1.4166(15) . ?
C9 H9 0.95 . ?
C2 C7 1.4199(13) . ?
C2 C3 1.4203(13) . ?
C7 C8 1.4172(16) . ?
C7 C6 1.4192(16) . ?
C10 H10 0.95 . ?
C21 C20 1.3953(15) . ?
C21 H21 0.95 . ?
C20 C19 1.3831(17) . ?
C17 C18 1.3918(13) . ?
C15 C14 1.5294(16) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C8 H8 0.95 . ?
C14 C16 1.5265(17) . ?
C14 H14 1 . ?
C5 C6 1.3683(18) . ?
C5 C4 1.4122(15) . ?
C5 H5 0.95 . ?
C19 C18 1.3940(14) . ?
C18 H18 0.95 . ?
C6 H6 0.95 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C11 C13 1.522(2) . ?
C11 C12 1.5265(17) . ?
C11 H11 1 . ?
C4 C3 1.3803(13) . ?
C4 H4 0.95 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
