#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/11/7051161.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_7051161
loop_
_publ_author_name
'Marek Necas'
'Mark R. St J. Foreman'
'Jaromír Marek'
'J. Derek Woollins'
'Josef Novosad'
_publ_section_title
;
 New mixed-donor unsymmetrical P--N--P ligands and their palladium(II)
 complexes
;
_journal_issue                   10
_journal_name_full               'New J. Chem.'
_journal_page_first              1256
_journal_page_last               1263
_journal_paper_doi               10.1039/b103501k
_journal_volume                  25
_journal_year                    2001
_chemical_formula_moiety         PhC(O)-NH-P(S)(OPh)2
_chemical_formula_sum            'C19 H16 N O3 P S'
_chemical_formula_weight         369.36
_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                76.93(3)
_cell_angle_beta                 70.93(3)
_cell_angle_gamma                68.82(3)
_cell_formula_units_Z            4
_cell_length_a                   9.974(2)
_cell_length_b                   13.675(3)
_cell_length_c                   15.078(3)
_cell_measurement_temperature    120(2)
_cell_volume                     1798.7(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.847
_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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12158
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.72
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    0.286
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     579
_refine_ls_number_reflns         7912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          6.309
_refine_ls_shift/su_mean         0.557
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0454P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0817
_reflns_number_gt                5947
_reflns_number_total             7912
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b103501k.txt
_cod_data_source_block           10.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0454P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0454P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1798.7(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7051161
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P2 P 0.13144(5) 0.29587(3) 0.85582(3) 0.01514(10) Uani 1 d . . .
S2 S -0.02584(5) 0.41051(4) 0.91482(3) 0.02330(11) Uani 1 d . . .
O6 O -0.00725(12) 0.32232(10) 0.70905(9) 0.0209(3) Uani 1 d . . .
O4 O 0.28762(12) 0.26569(9) 0.87709(8) 0.0180(3) Uani 1 d . . .
N2 N 0.20462(15) 0.30861(11) 0.73796(10) 0.0158(3) Uani 1 d . . .
O5 O 0.10075(12) 0.18538(9) 0.87814(9) 0.0196(3) Uani 1 d . . .
C20 C 0.29559(17) 0.23666(14) 0.97122(12) 0.0170(3) Uani 1 d . . .
C32 C 0.20173(18) 0.33089(13) 0.57343(12) 0.0167(3) Uani 1 d . . .
C38 C 0.12419(17) 0.31995(12) 0.67690(12) 0.0159(3) Uani 1 d . . .
C27 C -0.1268(2) 0.15049(16) 0.90337(17) 0.0307(5) Uani 1 d . . .
C26 C -0.03040(18) 0.16582(13) 0.94129(13) 0.0199(4) Uani 1 d . . .
C25 C 0.2760(2) 0.31334(15) 1.02347(13) 0.0233(4) Uani 1 d . . .
C23 C 0.3173(2) 0.17738(16) 1.15318(14) 0.0252(4) Uani 1 d . . .
C31 C -0.0549(2) 0.15809(16) 1.03732(14) 0.0305(4) Uani 1 d . . .
C24 C 0.2863(2) 0.28256(16) 1.11552(14) 0.0259(4) Uani 1 d . . .
C33 C 0.35611(19) 0.30915(15) 0.53598(13) 0.0226(4) Uani 1 d . . .
C37 C 0.1139(2) 0.36564(16) 0.51150(14) 0.0256(4) Uani 1 d . . .
C36 C 0.1795(2) 0.38021(18) 0.41462(14) 0.0318(5) Uani 1 d . . .
C34 C 0.4207(2) 0.32343(16) 0.43913(14) 0.0263(4) Uani 1 d . . .
C22 C 0.3377(2) 0.10176(16) 1.09921(14) 0.0265(4) Uani 1 d . . .
C35 C 0.3322(2) 0.35965(16) 0.37830(14) 0.0271(4) Uani 1 d . . .
C21 C 0.32702(19) 0.13101(14) 1.00698(13) 0.0227(4) Uani 1 d . . .
C29 C -0.2810(2) 0.11988(17) 1.06209(19) 0.0402(6) Uani 1 d . . .
C28 C -0.2545(2) 0.12866(17) 0.9661(2) 0.0428(6) Uani 1 d . . .
C30 C -0.1822(2) 0.13456(18) 1.09823(17) 0.0392(5) Uani 1 d . . .
P1 P 0.19465(5) 0.83253(3) 0.36435(3) 0.01700(10) Uani 1 d . . .
S1 S -0.01610(5) 0.89373(4) 0.38841(4) 0.02431(11) Uani 1 d . . .
O3 O 0.49659(12) 0.68396(10) 0.30744(9) 0.0214(3) Uani 1 d . . .
O2 O 0.29554(14) 0.90155(10) 0.29637(8) 0.0222(3) Uani 1 d . . .
O1 O 0.25916(13) 0.80075(10) 0.45263(8) 0.0198(3) Uani 1 d . . .
N1 N 0.25688(15) 0.72526(11) 0.30864(10) 0.0167(3) Uani 1 d . . .
C19 C 0.40638(17) 0.66528(13) 0.28183(12) 0.0168(3) Uani 1 d . . .
C17 C 0.4094(2) 0.49187(14) 0.11883(13) 0.0209(4) Uani 1 d . . .
C1 C 0.19372(18) 0.74950(13) 0.53983(12) 0.0171(3) Uani 1 d . . .
C6 C 0.1137(2) 0.80843(16) 0.61408(14) 0.0238(4) Uani 1 d . . .
C14 C 0.59185(19) 0.50594(14) 0.21357(14) 0.0228(4) Uani 1 d . . .
C13 C 0.44990(17) 0.58012(13) 0.22227(12) 0.0160(3) Uani 1 d . . .
C15 C 0.6409(2) 0.42487(15) 0.15869(14) 0.0266(4) Uani 1 d . . .
C8 C 0.2964(2) 1.02287(14) 0.39072(13) 0.0214(4) Uani 1 d . . .
C11 C 0.6014(2) 0.98055(16) 0.30303(15) 0.0277(4) Uani 1 d . . .
C9 C 0.3766(2) 1.07278(15) 0.41310(14) 0.0279(4) Uani 1 d . . .
C18 C 0.35876(19) 0.57274(13) 0.17428(12) 0.0175(4) Uani 1 d . . .
C7 C 0.37167(18) 0.95220(13) 0.32488(12) 0.0167(3) Uani 1 d . . .
C2 C 0.2190(2) 0.64212(15) 0.55017(15) 0.0272(4) Uani 1 d . . .
C3 C 0.1605(3) 0.59319(17) 0.63841(17) 0.0367(5) Uani 1 d . . .
C12 C 0.52251(19) 0.93051(14) 0.27978(13) 0.0211(4) Uani 1 d . . .
C16 C 0.5498(2) 0.41739(15) 0.11132(14) 0.0249(4) Uani 1 d . . .
C5 C 0.0558(2) 0.75824(18) 0.70223(15) 0.0339(5) Uani 1 d . . .
C4 C 0.0797(2) 0.6502(2) 0.71390(17) 0.0393(6) Uani 1 d . . .
C10 C 0.5288(2) 1.05131(17) 0.36966(15) 0.0315(5) Uani 1 d . . .
H16 H 0.581(2) 0.3603(19) 0.0732(17) 0.029(7) Uiso 1 d . . .
H34 H 0.527(3) 0.3074(18) 0.4144(16) 0.028(7) Uiso 1 d . . .
H14 H 0.652(3) 0.5088(18) 0.2472(17) 0.029(7) Uiso 1 d . . .
H25 H 0.253(2) 0.3860(19) 0.9986(17) 0.032(7) Uiso 1 d . . .
H12 H 0.567(3) 0.8823(19) 0.2344(17) 0.023(7) Uiso 1 d . . .
H17 H 0.348(2) 0.4859(18) 0.0855(17) 0.026(7) Uiso 1 d . . .
H33 H 0.417(3) 0.2838(18) 0.5743(17) 0.035(7) Uiso 1 d . . .
H1N H 0.192(3) 0.7065(18) 0.3007(17) 0.042(7) Uiso 1 d . . .
H18 H 0.260(3) 0.6252(18) 0.1769(16) 0.033(7) Uiso 1 d . . .
H6 H 0.101(2) 0.879(2) 0.6034(17) 0.033(7) Uiso 1 d . . .
H35 H 0.379(2) 0.3716(18) 0.3119(17) 0.027(7) Uiso 1 d . . .
H22 H 0.357(3) 0.0307(19) 1.1262(17) 0.035(7) Uiso 1 d . . .
H21 H 0.339(2) 0.0783(19) 0.9689(17) 0.036(7) Uiso 1 d . . .
H9 H 0.335(2) 1.1215(19) 0.4554(17) 0.033(7) Uiso 1 d . . .
H37 H 0.009(3) 0.3813(18) 0.5383(17) 0.035(7) Uiso 1 d . . .
H8 H 0.192(3) 1.0337(18) 0.4215(17) 0.029(7) Uiso 1 d . . .
H27 H -0.100(2) 0.1532(19) 0.8328(18) 0.046(7) Uiso 1 d . . .
H11 H 0.705(3) 0.9669(18) 0.2733(16) 0.042(7) Uiso 1 d . . .
H23 H 0.324(3) 0.1574(19) 1.2170(17) 0.036(7) Uiso 1 d . . .
H2N H 0.288(3) 0.3125(19) 0.7179(17) 0.035(7) Uiso 1 d . . .
H2 H 0.280(3) 0.6030(19) 0.4995(17) 0.044(7) Uiso 1 d . . .
H15 H 0.742(3) 0.3738(18) 0.1522(16) 0.046(7) Uiso 1 d . . .
H24 H 0.275(3) 0.3341(19) 1.1534(17) 0.038(7) Uiso 1 d . . .
H31 H 0.017(2) 0.1663(18) 1.0629(16) 0.053(7) Uiso 1 d . . .
H10 H 0.583(2) 1.0843(18) 0.3889(16) 0.043(7) Uiso 1 d . . .
H36 H 0.122(3) 0.4047(19) 0.3699(17) 0.043(7) Uiso 1 d . . .
H4 H 0.038(2) 0.6187(19) 0.7746(18) 0.050(7) Uiso 1 d . . .
H30 H -0.199(3) 0.1263(18) 1.1710(18) 0.050(7) Uiso 1 d . . .
H3 H 0.176(2) 0.5165(19) 0.6481(16) 0.057(7) Uiso 1 d . . .
H29 H -0.369(3) 0.1034(19) 1.1054(17) 0.053(7) Uiso 1 d . . .
H5 H 0.000(3) 0.8023(19) 0.7542(17) 0.043(7) Uiso 1 d . . .
H28 H -0.322(3) 0.1174(18) 0.9381(17) 0.058(7) Uiso 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'
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'
P P 0.1023 0.0942 '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
O4 P2 O5 102.68(7) . . ?
O4 P2 N2 93.56(7) . . ?
O5 P2 N2 103.50(8) . . ?
O4 P2 S2 116.96(5) . . ?
O5 P2 S2 116.44(5) . . ?
N2 P2 S2 120.08(6) . . ?
C20 O4 P2 118.99(10) . . ?
C38 N2 P2 122.19(12) . . ?
C26 O5 P2 124.70(11) . . ?
C25 C20 C21 122.35(17) . . ?
C25 C20 O4 119.18(16) . . ?
C21 C20 O4 118.45(16) . . ?
C37 C32 C33 118.20(17) . . ?
C37 C32 C38 117.32(15) . . ?
C33 C32 C38 124.48(15) . . ?
O6 C38 N2 118.79(16) . . ?
O6 C38 C32 124.01(15) . . ?
N2 C38 C32 117.19(14) . . ?
C26 C27 C28 117.5(2) . . ?
C27 C26 C31 121.61(18) . . ?
C27 C26 O5 117.62(17) . . ?
C31 C26 O5 120.71(16) . . ?
C20 C25 C24 118.06(18) . . ?
C22 C23 C24 120.14(18) . . ?
C26 C31 C30 119.6(2) . . ?
C25 C24 C23 120.78(19) . . ?
C34 C33 C32 121.58(17) . . ?
C32 C37 C36 119.84(18) . . ?
C35 C36 C37 121.53(19) . . ?
C35 C34 C33 119.74(18) . . ?
C23 C22 C21 119.99(19) . . ?
C34 C35 C36 119.10(19) . . ?
C20 C21 C22 118.67(18) . . ?
C30 C29 C28 119.3(2) . . ?
C29 C28 C27 122.0(2) . . ?
C29 C30 C31 119.9(2) . . ?
O1 P1 O2 100.57(7) . . ?
O1 P1 N1 107.37(8) . . ?
O2 P1 N1 101.79(7) . . ?
O1 P1 S1 116.42(6) . . ?
O2 P1 S1 117.64(6) . . ?
N1 P1 S1 111.45(6) . . ?
C7 O2 P1 125.83(11) . . ?
C1 O1 P1 123.50(10) . . ?
C19 N1 P1 123.75(12) . . ?
O3 C19 N1 119.26(15) . . ?
O3 C19 C13 122.15(15) . . ?
N1 C19 C13 118.59(14) . . ?
C18 C17 C16 121.41(17) . . ?
C2 C1 C6 121.95(18) . . ?
C2 C1 O1 119.72(17) . . ?
C6 C1 O1 118.20(15) . . ?
C1 C6 C5 119.17(19) . . ?
C15 C14 C13 121.11(17) . . ?
C18 C13 C14 119.14(16) . . ?
C18 C13 C19 123.10(15) . . ?
C14 C13 C19 117.74(15) . . ?
C16 C15 C14 119.68(17) . . ?
C9 C8 C7 117.96(17) . . ?
C12 C11 C10 119.80(18) . . ?
C8 C9 C10 119.92(19) . . ?
C13 C18 C17 119.32(16) . . ?
C8 C7 C12 123.21(16) . . ?
C8 C7 O2 120.85(15) . . ?
C12 C7 O2 115.87(15) . . ?
C1 C2 C3 118.2(2) . . ?
C4 C3 C2 121.1(2) . . ?
C11 C12 C7 118.21(17) . . ?
C15 C16 C17 119.34(17) . . ?
C4 C5 C6 119.7(2) . . ?
C3 C4 C5 119.9(2) . . ?
C11 C10 C9 120.87(18) . . ?
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
P2 O4 1.5816(12) . ?
P2 O5 1.5897(12) . ?
P2 N2 1.6809(16) . ?
P2 S2 1.9109(10) . ?
O6 C38 1.2312(19) . ?
O4 C20 1.405(2) . ?
N2 C38 1.358(2) . ?
O5 C26 1.419(2) . ?
C20 C25 1.372(2) . ?
C20 C21 1.381(2) . ?
C32 C37 1.377(2) . ?
C32 C33 1.398(2) . ?
C32 C38 1.498(2) . ?
C27 C26 1.361(3) . ?
C27 C28 1.402(3) . ?
C26 C31 1.373(3) . ?
C25 C24 1.383(3) . ?
C23 C22 1.376(3) . ?
C23 C24 1.382(3) . ?
C31 C30 1.400(3) . ?
C33 C34 1.390(3) . ?
C37 C36 1.393(3) . ?
C36 C35 1.384(3) . ?
C34 C35 1.369(3) . ?
C22 C21 1.386(3) . ?
C29 C30 1.360(3) . ?
C29 C28 1.369(4) . ?
P1 O1 1.5718(13) . ?
P1 O2 1.5902(14) . ?
P1 N1 1.6738(15) . ?
P1 S1 1.9022(9) . ?
O3 C19 1.2090(19) . ?
O2 C7 1.4032(19) . ?
O1 C1 1.414(2) . ?
N1 C19 1.390(2) . ?
C19 C13 1.485(2) . ?
C17 C18 1.384(2) . ?
C17 C16 1.389(3) . ?
C1 C2 1.378(2) . ?
C1 C6 1.378(3) . ?
C6 C5 1.394(3) . ?
C14 C15 1.382(3) . ?
C14 C13 1.397(2) . ?
C13 C18 1.374(2) . ?
C15 C16 1.367(3) . ?
C8 C9 1.377(3) . ?
C8 C7 1.380(2) . ?
C11 C12 1.374(3) . ?
C11 C10 1.389(3) . ?
C9 C10 1.390(3) . ?
C7 C12 1.384(2) . ?
C2 C3 1.389(3) . ?
C3 C4 1.378(3) . ?
C5 C4 1.388(3) . ?
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
N1 H1N O6 0.83(2) 2.07(2) 2.8942(18) 172(2) 2_566
N2 H2N O3 0.80(2) 2.08(2) 2.8661(19) 169(2) 2_666
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652868
2 PubChem 139175400
