#------------------------------------------------------------------------------
#$Date: 2023-04-13 15:19:33 +0300 (Thu, 13 Apr 2023) $
#$Revision: 282621 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/84/1568424.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_1568424
loop_
_publ_author_name
'Naksomboon, Kananat'
'Gómez-Bengoa, Enrique'
'Mehara, Jaya'
'Roithová, Jana'
'Otten, Edwin'
'Fernández-Ibáñez, M. Ángeles'
_publ_section_title
;
 Mechanistic studies of the palladium-catalyzed S,O-ligand promoted C--H
 olefination of aromatic compounds
;
_journal_issue                   11
_journal_name_full               'Chemical Science'
_journal_page_first              2943
_journal_page_last               2953
_journal_paper_doi               10.1039/D2SC06840K
_journal_volume                  14
_journal_year                    2023
_chemical_formula_sum            'C20 H22 O4 Pd S2'
_chemical_formula_weight         496.89
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc1plpnm
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-08-06 deposited with the CCDC.	2023-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                81.443(2)
_cell_angle_beta                 73.982(2)
_cell_angle_gamma                76.298(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0235(3)
_cell_length_b                   10.1775(4)
_cell_length_c                   11.8976(5)
_cell_measurement_reflns_used    126
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.9018
_cell_measurement_theta_min      4.0035
_cell_volume                     1016.25(7)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest ECO PHOTON 50'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15108
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.035
_diffrn_reflns_theta_max         25.035
_diffrn_reflns_theta_min         2.609
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.141
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.479
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.114
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.883
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0265
_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/[σ²(Fo²)+(0.1000P)²+0.2968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3128
_reflns_number_total             3577
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc06840k2.cif
_cod_data_source_block           CVC613_0m_a
_cod_depositor_comments
'Adding full bibliography for 1568424--1568427.cif.'
_cod_database_code               1568424
#BEGIN Tags that were not found in dictionaries:
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.611
_shelx_estimated_absorpt_t_max   0.881
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_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
Pd1 Pd 0.29686(3) 0.55599(2) 0.30546(2) 0.01776(13) Uani 1 1 d . . . . .
S1 S 0.42914(9) 0.39888(8) 0.41697(7) 0.0186(2) Uani 1 1 d . . . . .
S2 S 0.43562(10) 0.71951(8) 0.28728(7) 0.0187(2) Uani 1 1 d . . . . .
O1 O 0.1637(2) 0.4182(2) 0.31668(19) 0.0171(5) Uani 1 1 d . . . . .
O2 O 0.1734(3) 0.6870(2) 0.2021(2) 0.0195(5) Uani 1 1 d . . . . .
O3 O 0.0916(3) 0.2282(3) 0.4021(2) 0.0324(6) Uani 1 1 d . . . . .
O4 O 0.1186(3) 0.8939(3) 0.1183(2) 0.0331(6) Uani 1 1 d . . . . .
C1 C 0.1681(4) 0.3143(3) 0.3934(3) 0.0207(7) Uani 1 1 d . . . . .
C2 C 0.2697(4) 0.3032(3) 0.4809(3) 0.0196(7) Uani 1 1 d . . . . .
C15 C 0.5904(4) 0.6954(3) 0.1552(3) 0.0199(7) Uani 1 1 d . . . . .
C12 C 0.2791(4) 0.8625(3) 0.2526(3) 0.0241(7) Uani 1 1 d . . . . .
C3 C 0.3388(4) 0.1558(3) 0.5161(3) 0.0253(7) Uani 1 1 d . . . . .
H3A H 0.4080 0.1532 0.5652 0.038 Uiso 1 1 calc R U . . .
H3B H 0.3968 0.1108 0.4469 0.038 Uiso 1 1 calc R U . . .
H3C H 0.2550 0.1106 0.5583 0.038 Uiso 1 1 calc R U . . .
C4 C 0.1698(4) 0.3788(4) 0.5868(3) 0.0273(8) Uani 1 1 d . . . . .
H4A H 0.1273 0.4704 0.5609 0.041 Uiso 1 1 calc R U . . .
H4B H 0.2340 0.3796 0.6389 0.041 Uiso 1 1 calc R U . . .
H4C H 0.0851 0.3339 0.6273 0.041 Uiso 1 1 calc R U . . .
C5 C 0.5722(4) 0.2955(3) 0.3131(3) 0.0205(7) Uani 1 1 d . . . . .
C6 C 0.5393(4) 0.2532(3) 0.2194(3) 0.0247(7) Uani 1 1 d . . . . .
H6 H 0.4382 0.2787 0.2077 0.030 Uiso 1 1 calc R U . . .
C11 C 0.1851(4) 0.8129(3) 0.1830(3) 0.0218(7) Uani 1 1 d . . . . .
C16 C 0.6006(4) 0.6009(4) 0.0793(3) 0.0273(8) Uani 1 1 d . . . . .
H16 H 0.5199 0.5541 0.0910 0.033 Uiso 1 1 calc R U . . .
C17 C 0.7315(5) 0.5768(4) -0.0138(3) 0.0352(9) Uani 1 1 d . . . . .
H17 H 0.7404 0.5113 -0.0635 0.042 Uiso 1 1 calc R U . . .
C10 C 0.7248(4) 0.2603(4) 0.3293(3) 0.0314(8) Uani 1 1 d . . . . .
H10 H 0.7472 0.2898 0.3920 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3489(5) 0.9824(4) 0.1879(4) 0.0325(9) Uani 1 1 d . . . . .
H14A H 0.2660 1.0559 0.1725 0.049 Uiso 1 1 calc R U . . .
H14B H 0.4210 0.9563 0.1150 0.049 Uiso 1 1 calc R U . . .
H14C H 0.4040 1.0111 0.2353 0.049 Uiso 1 1 calc R U . . .
C7 C 0.6579(4) 0.1726(4) 0.1428(3) 0.0306(8) Uani 1 1 d . . . . .
H7 H 0.6359 0.1429 0.0801 0.037 Uiso 1 1 calc R U . . .
C20 C 0.7094(4) 0.7671(4) 0.1377(3) 0.0307(8) Uani 1 1 d . . . . .
H20 H 0.7022 0.8298 0.1894 0.037 Uiso 1 1 calc R U . . .
C19 C 0.8389(5) 0.7442(5) 0.0423(4) 0.0406(10) Uani 1 1 d . . . . .
H19 H 0.9185 0.7926 0.0293 0.049 Uiso 1 1 calc R U . . .
C13 C 0.1697(4) 0.8957(4) 0.3739(3) 0.0296(8) Uani 1 1 d . . . . .
H13A H 0.2285 0.9196 0.4210 0.044 Uiso 1 1 calc R U . . .
H13B H 0.1273 0.8178 0.4119 0.044 Uiso 1 1 calc R U . . .
H13C H 0.0850 0.9705 0.3644 0.044 Uiso 1 1 calc R U . . .
C8 C 0.8087(4) 0.1357(4) 0.1589(4) 0.0356(9) Uani 1 1 d . . . . .
H8 H 0.8874 0.0807 0.1076 0.043 Uiso 1 1 calc R U . . .
C18 C 0.8500(5) 0.6491(4) -0.0340(4) 0.0373(9) Uani 1 1 d . . . . .
H18 H 0.9364 0.6342 -0.0982 0.045 Uiso 1 1 calc R U . . .
C9 C 0.8426(4) 0.1805(4) 0.2508(4) 0.0391(10) Uani 1 1 d . . . . .
H9 H 0.9448 0.1573 0.2603 0.047 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 0.0000 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acscatal.7b02356 2017
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
O1 Pd1 O2 90.77(9) . . ?
O1 Pd1 S1 85.73(6) . . ?
O2 Pd1 S1 176.21(6) . . ?
O1 Pd1 S2 176.47(6) . . ?
O2 Pd1 S2 85.73(7) . . ?
S1 Pd1 S2 97.78(3) . . ?
C5 S1 C2 105.68(15) . . ?
C5 S1 Pd1 103.70(11) . . ?
C2 S1 Pd1 96.44(11) . . ?
C15 S2 C12 107.27(16) . . ?
C15 S2 Pd1 106.46(11) . . ?
C12 S2 Pd1 95.59(11) . . ?
C1 O1 Pd1 120.7(2) . . ?
C11 O2 Pd1 120.3(2) . . ?
O3 C1 O1 122.8(3) . . ?
O3 C1 C2 119.0(3) . . ?
O1 C1 C2 118.2(3) . . ?
C4 C2 C3 112.1(3) . . ?
C4 C2 C1 108.5(3) . . ?
C3 C2 C1 111.9(3) . . ?
C4 C2 S1 103.7(2) . . ?
C3 C2 S1 110.4(2) . . ?
C1 C2 S1 109.9(2) . . ?
C16 C15 C20 120.8(3) . . ?
C16 C15 S2 122.3(3) . . ?
C20 C15 S2 116.6(3) . . ?
C14 C12 C13 111.9(3) . . ?
C14 C12 C11 112.4(3) . . ?
C13 C12 C11 108.2(3) . . ?
C14 C12 S2 110.8(3) . . ?
C13 C12 S2 103.7(2) . . ?
C11 C12 S2 109.4(2) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 120.5(3) . . ?
C6 C5 S1 123.3(2) . . ?
C10 C5 S1 116.2(3) . . ?
C5 C6 C7 119.5(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
O4 C11 O2 122.8(3) . . ?
O4 C11 C12 119.2(3) . . ?
O2 C11 C12 117.9(3) . . ?
C17 C16 C15 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 120.6(4) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C9 C10 C5 119.2(4) . . ?
C9 C10 H10 120.4 . . ?
C5 C10 H10 120.4 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C7 C6 120.5(4) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C19 C20 C15 119.3(3) . . ?
C19 C20 H20 120.3 . . ?
C15 C20 H20 120.3 . . ?
C20 C19 C18 120.1(4) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C17 C18 C19 119.7(4) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C8 C9 C10 120.3(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
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
Pd1 O1 2.021(2) . ?
Pd1 O2 2.024(2) . ?
Pd1 S1 2.2538(8) . ?
Pd1 S2 2.2616(8) . ?
S1 C5 1.779(3) . ?
S1 C2 1.853(3) . ?
S2 C15 1.795(3) . ?
S2 C12 1.858(3) . ?
O1 C1 1.290(4) . ?
O2 C11 1.292(4) . ?
O3 C1 1.215(4) . ?
O4 C11 1.210(4) . ?
C1 C2 1.543(4) . ?
C2 C4 1.525(5) . ?
C2 C3 1.527(4) . ?
C15 C16 1.385(5) . ?
C15 C20 1.389(5) . ?
C12 C14 1.516(5) . ?
C12 C13 1.541(5) . ?
C12 C11 1.541(5) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.379(5) . ?
C5 C10 1.398(5) . ?
C6 C7 1.385(5) . ?
C6 H6 0.9300 . ?
C16 C17 1.380(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(6) . ?
C17 H17 0.9300 . ?
C10 C9 1.390(6) . ?
C10 H10 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C7 C8 1.382(5) . ?
C7 H7 0.9300 . ?
C20 C19 1.388(5) . ?
C20 H20 0.9300 . ?
C19 C18 1.391(6) . ?
C19 H19 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C8 C9 1.376(6) . ?
C8 H8 0.9300 . ?
C18 H18 0.9300 . ?
C9 H9 0.9300 . ?
