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#$Date: 2023-08-05 12:29:20 +0300 (Sat, 05 Aug 2023) $
#$Revision: 285503 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/94/7159431.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_7159431
loop_
_publ_author_name
'Moreno-Rodriguez, Nazaret'
'Borrego, L. Gabriel'
'Recio, Rocío'
'Valdivia, Victoria'
'Nicasio, M. Carmen'
'Álvarez, Eleuterio'
'Khiar, Noureddine'
'Fernández, Inmaculada'
_publ_section_title
;
 Synthesis and characterization of enantiopure chiral NH₂/SO
 palladium complexes.
;
_journal_issue                   28
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5827
_journal_page_last               5839
_journal_paper_doi               10.1039/d3ob00816a
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H17 Cl2 N O Pd S'
_chemical_formula_sum            'C11 H17 Cl2 N O Pd S'
_chemical_formula_weight         388.61
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-05-09 deposited with the CCDC.	2023-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1116(5)
_cell_length_b                   12.0151(7)
_cell_length_c                   14.6744(7)
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.78
_cell_volume                     1430.19(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 7.37
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
; 
 Bruker-AXS, D8 QUEST ECO, PHOTON II area detector 
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27751
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.539
_diffrn_reflns_theta_min         2.191
_diffrn_source                   'I\mS microfocus'
_exptl_absorpt_coefficient_mu    1.800
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
program SADABS, Bruker (2001).
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
; 
 Flack x determined using 1633 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.003(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         4379
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0261
_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/[σ²(Fo²)+(0.0116P)²+0.6834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0472
_refine_ls_wR_factor_ref         0.0484
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4066
_reflns_number_total             4379
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00816a2.cif
_cod_data_source_block           15_Sc_Rs
_cod_depositor_comments
'Adding full bibliography for 7159420--7159436.cif.'
_cod_database_code               7159431
_shelx_shelxl_version_number     2018/3
_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   0.715
_shelx_estimated_absorpt_t_max   0.948
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -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
Pd1 Pd 0.43738(3) 0.24889(2) 0.88472(2) 0.01892(6) Uani 1 1 d . . . . .
Cl1 Cl 0.29804(11) 0.36520(7) 0.98444(5) 0.02462(17) Uani 1 1 d . . . . .
Cl2 Cl 0.21887(12) 0.12848(8) 0.87214(7) 0.0359(2) Uani 1 1 d . . . . .
S1 S 0.57996(11) 0.15369(7) 0.78385(6) 0.02104(16) Uani 1 1 d . . . . .
O1 O 0.6018(3) 0.0330(2) 0.7886(2) 0.0341(6) Uani 1 1 d . . . . .
N1 N 0.6437(3) 0.3460(2) 0.89641(19) 0.0218(6) Uani 1 1 d . . . . .
H1A H 0.611332 0.417780 0.904730 0.026 Uiso 1 1 calc R U . . .
H1B H 0.699519 0.324706 0.947312 0.026 Uiso 1 1 calc R U . . .
C1 C 0.7785(4) 0.2201(3) 0.7901(2) 0.0230(7) Uani 1 1 d . . . . .
H1C H 0.848178 0.181136 0.835386 0.028 Uiso 1 1 calc R U . . .
H1D H 0.833877 0.215403 0.730108 0.028 Uiso 1 1 calc R U . . .
C2 C 0.7595(4) 0.3421(3) 0.8175(2) 0.0211(7) Uani 1 1 d . . . . .
H2 H 0.709387 0.383895 0.765486 0.025 Uiso 1 1 calc R U . . .
C3 C 0.9287(5) 0.3935(3) 0.8396(2) 0.0272(7) Uani 1 1 d . . . . .
H3 H 0.983021 0.346481 0.887054 0.033 Uiso 1 1 calc R U . . .
C4 C 1.0369(5) 0.3934(4) 0.7553(3) 0.0377(10) Uani 1 1 d . . . . .
H4A H 0.982407 0.435395 0.706558 0.057 Uiso 1 1 calc R U . . .
H4B H 1.055171 0.316638 0.735204 0.057 Uiso 1 1 calc R U . . .
H4C H 1.143048 0.428246 0.769597 0.057 Uiso 1 1 calc R U . . .
C5 C 0.9114(5) 0.5111(3) 0.8772(3) 0.0400(9) Uani 1 1 d . . . . .
H5A H 1.021161 0.543152 0.886861 0.060 Uiso 1 1 calc R U . . .
H5B H 0.851791 0.508794 0.935200 0.060 Uiso 1 1 calc R U . . .
H5C H 0.850266 0.557147 0.833588 0.060 Uiso 1 1 calc R U . . .
C6 C 0.5112(4) 0.1880(3) 0.6725(2) 0.0208(7) Uani 1 1 d . . . . .
C7 C 0.5393(4) 0.1117(3) 0.6039(2) 0.0277(7) Uani 1 1 d . . . . .
H7 H 0.596465 0.044336 0.616068 0.033 Uiso 1 1 calc R U . . .
C8 C 0.4824(5) 0.1353(4) 0.5169(3) 0.0379(10) Uani 1 1 d . . . . .
H8 H 0.497982 0.082944 0.469122 0.045 Uiso 1 1 calc R U . . .
C9 C 0.4037(5) 0.2340(4) 0.4998(2) 0.0405(11) Uani 1 1 d . . . . .
H9 H 0.364150 0.249509 0.440202 0.049 Uiso 1 1 calc R U . . .
C10 C 0.3812(6) 0.3113(4) 0.5686(3) 0.0389(10) Uani 1 1 d . . . . .
H10 H 0.329830 0.380562 0.555567 0.047 Uiso 1 1 calc R U . . .
C11 C 0.4334(5) 0.2880(3) 0.6564(2) 0.0281(7) Uani 1 1 d . . . . .
H11 H 0.416095 0.339793 0.704368 0.034 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
Pd Pd -0.9988 1.0072 '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'
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
N1 Pd1 S1 85.57(8) . . ?
N1 Pd1 Cl2 175.66(9) . . ?
S1 Pd1 Cl2 91.39(3) . . ?
N1 Pd1 Cl1 90.13(8) . . ?
S1 Pd1 Cl1 174.25(3) . . ?
Cl2 Pd1 Cl1 93.11(3) . . ?
O1 S1 C6 108.18(16) . . ?
O1 S1 C1 109.19(16) . . ?
C6 S1 C1 103.01(16) . . ?
O1 S1 Pd1 123.20(12) . . ?
C6 S1 Pd1 109.47(11) . . ?
C1 S1 Pd1 101.87(11) . . ?
C2 N1 Pd1 115.6(2) . . ?
C2 N1 H1A 108.4 . . ?
Pd1 N1 H1A 108.4 . . ?
C2 N1 H1B 108.4 . . ?
Pd1 N1 H1B 108.4 . . ?
H1A N1 H1B 107.4 . . ?
C2 C1 S1 110.4(2) . . ?
C2 C1 H1C 109.6 . . ?
S1 C1 H1C 109.6 . . ?
C2 C1 H1D 109.6 . . ?
S1 C1 H1D 109.6 . . ?
H1C C1 H1D 108.1 . . ?
N1 C2 C1 107.3(3) . . ?
N1 C2 C3 112.7(3) . . ?
C1 C2 C3 110.5(3) . . ?
N1 C2 H2 108.7 . . ?
C1 C2 H2 108.7 . . ?
C3 C2 H2 108.7 . . ?
C4 C3 C5 110.4(3) . . ?
C4 C3 C2 110.1(3) . . ?
C5 C3 C2 111.5(3) . . ?
C4 C3 H3 108.2 . . ?
C5 C3 H3 108.2 . . ?
C2 C3 H3 108.2 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 122.0(3) . . ?
C11 C6 S1 120.3(3) . . ?
C7 C6 S1 117.7(3) . . ?
C6 C7 C8 118.7(4) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C9 C8 C7 120.0(4) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.6(4) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 120.2(4) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C6 C11 C10 118.4(3) . . ?
C6 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
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 N1 2.047(3) . ?
Pd1 S1 2.1993(8) . ?
Pd1 Cl2 2.2953(9) . ?
Pd1 Cl1 2.3177(9) . ?
S1 O1 1.462(3) . ?
S1 C6 1.776(4) . ?
S1 C1 1.800(3) . ?
N1 C2 1.491(4) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
C1 C2 1.528(5) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C2 C3 1.539(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.517(5) . ?
C3 C5 1.523(5) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.377(5) . ?
C6 C7 1.380(4) . ?
C7 C8 1.387(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.370(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1B Cl2 0.91 2.71 3.464(3) 140.5 4_557 yes
N1 H1B Cl1 0.91 2.62 3.326(3) 135.3 4_557 yes
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 C1 C2 -160.9(2) . . . . ?
C6 S1 C1 C2 84.3(3) . . . . ?
Pd1 S1 C1 C2 -29.2(2) . . . . ?
Pd1 N1 C2 C1 -44.4(3) . . . . ?
Pd1 N1 C2 C3 -166.3(2) . . . . ?
S1 C1 C2 N1 46.7(3) . . . . ?
S1 C1 C2 C3 169.9(2) . . . . ?
N1 C2 C3 C4 -176.6(3) . . . . ?
C1 C2 C3 C4 63.3(4) . . . . ?
N1 C2 C3 C5 -53.6(4) . . . . ?
C1 C2 C3 C5 -173.7(3) . . . . ?
O1 S1 C6 C11 160.1(3) . . . . ?
C1 S1 C6 C11 -84.4(3) . . . . ?
Pd1 S1 C6 C11 23.4(3) . . . . ?
O1 S1 C6 C7 -20.3(3) . . . . ?
C1 S1 C6 C7 95.3(3) . . . . ?
Pd1 S1 C6 C7 -156.9(2) . . . . ?
C11 C6 C7 C8 -2.2(6) . . . . ?
S1 C6 C7 C8 178.1(3) . . . . ?
C6 C7 C8 C9 1.6(6) . . . . ?
C7 C8 C9 C10 0.5(7) . . . . ?
C8 C9 C10 C11 -2.1(7) . . . . ?
C7 C6 C11 C10 0.6(6) . . . . ?
S1 C6 C11 C10 -179.8(3) . . . . ?
C9 C10 C11 C6 1.6(7) . . . . ?
