metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

Bis[S-hexyl 3-(thio­phen-2-yl­methyl­­idene)di­thio­carbazato-κ2N3,S]palladium(II)

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aDepartment of Physics, Shahjalal University of Science and Technology, Sylhet 3114, Bangladesh, bDepartment of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan, cCenter for Environmental Conservation and Research Safety, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan, dDepartment of Chemical and Pharmaceutical Sciences, via Giorgieri 1, 34127 Trieste, Italy, and eDepartment of Chemistry, Shahjalal University of Science and Technology, Sylhet 3114, Bangladesh
*Correspondence e-mail: china@sust.edu

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 15 June 2016; accepted 12 July 2016; online 19 July 2016)

In the title complex, [Pd(C12H17N2S3)2], the PdII atom exhibits a square-planar coordination geometry with the N,S-chelating ligands arranged in a trans configuration. Intra­molecular C—H⋯S hydrogen bonds are observed. In the crystal, mol­ecules are linked by weak C—H⋯N hydrogen-bond inter­actions, forming chains parallel to the b axis.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The title compound is isomorphous and isotypic to the bis­chelated copper(II) and nickel(II) complexes (Begum et al., 2016[Begum, M. S., Zangrando, E., Howlader, M. B. H., Sheikh, M. C., Miyatake, R., Hossain, M. M., Alam, M. M. & Hasnat, M. A. (2016). Polyhedron, 105, 56-61.]). In the complex (Fig. 1[link]), the two Schiff bases, in their deprotonated imino thiol­ate form, chelate the metal centre via the N1/N3 azomethine nitro­gen and S2/S5 thiol­ate sulfur atoms in a trans-planar configuration exhibiting a pseudo-centrosymmetric arrangement. The mol­ecular structure of similar non-coordinating ligands (Begum, Howlader et al., 2015[Begum, M. S., Howlader, M. B. H., Miyatake, R., Zangrando, E. & Sheikh, M. C. (2015). Acta Cryst. E71, o199.]; Begum, Zangrando et al., 2015[Begum, M. S., Zangrando, E., Sheikh, M. C., Miyatake, R. & Hossain, M. M. (2015). Acta Cryst. E71, o265-o266.]) shows the β-nitro­gen and the thio­keto sulfur atoms are trans located with respect to the C6—N2 bond. Thus, upon coordination the deprotonated ligand requires rotation by 180° about this C—N bond in order to allow the N,S chelating behavior towards the metal. In the complex the ligand shows some geometrical variations with respect to the free species, the most significant being an elongation of the thio­keto C6—S2 bond length with a concomitant decrease of the N1—C5 and increase of the N—N bond lengths. The mol­ecular conformation is enforced by intramolecular C—H⋯S hydrogen bonds (Table 1[link]). The hexyl chains exhibit all carbon atoms in an anti conformation, this conformation being recognized as an energy minimum. In the crystal (Fig. 2[link]), mol­ecules are arranged with the alkyl chains giving rise to a hydro­phobic region and forming chains parallel to the b axis via weak C—H⋯N hydrogen bonds (Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C5—H4⋯S5 0.95 2.62 3.2970 (17) 129
C15—H20⋯N4i 0.95 2.62 3.4088 (19) 141
C17—H21⋯S2 0.95 2.63 3.2596 (16) 124
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].
[Figure 1]
Figure 1
The mol­ecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.
[Figure 2]
Figure 2
Crystal packing of the title complex viewed down the b axis.

Synthesis and crystallization

The title complex was prepared following a previously reported method (Begum et al., 2016[Begum, M. S., Zangrando, E., Howlader, M. B. H., Sheikh, M. C., Miyatake, R., Hossain, M. M., Alam, M. M. & Hasnat, M. A. (2016). Polyhedron, 105, 56-61.]). A solution of PdCl2 (0.044 g, 0.25 mmol) in 25 ml methanol was added to a solution of S-hexyl-3-(2-thienyl­idene)di­thio­carbazate (0.144 g, 0.5 mmol) in 10 ml methanol. The resulting mixture was refluxed with constant stirring for 4 h. The orange–red precipitate formed was filtered off, washed with methanol and dried in vacuo over anhydrous CaCl2. Orange–red single crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation from a mixture of di­chloro­methane and aceto­nitrile (3:1 v/v). M.p. = 352 K.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula [Pd(C12H17N2S3)2]
Mr 677.32
Crystal system, space group Monoclinic, P21/c
Temperature (K) 173
a, b, c (Å) 13.9118 (3), 10.37486 (19), 20.6696 (4)
β (°) 103.9290 (7)
V3) 2895.58 (10)
Z 4
Radiation type Mo Kα
μ (mm−1) 1.10
Crystal size (mm) 0.29 × 0.16 × 0.09
 
Data collection
Diffractometer Rigaku R-AXIS RAPID
Absorption correction Multi-scan (ABSCOR; Rigaku, 1995[Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.])
Tmin, Tmax 0.653, 0.906
No. of measured, independent and observed [F2 > 2.0σ(F2)] reflections 27863, 6611, 5991
Rint 0.026
(sin θ/λ)max−1) 0.649
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.021, 0.055, 1.08
No. of reflections 6611
No. of parameters 318
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.46, −0.41
Computer programs: RAPID-AUTO (Rigaku, 2010[Rigaku (2010). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]), SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]), SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data


Computing details top

Data collection: RAPID-AUTO (Rigaku, 2010); cell refinement: RAPID-AUTO (Rigaku, 2010); data reduction: RAPID-AUTO (Rigaku, 2010); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

Bis[S-hexyl 3-(thiophen-2-ylmethylidene)dithiocarbazato-κ2N3,S]palladium(II) top
Crystal data top
[Pd(C12H17N2S3)2]F(000) = 1392.00
Mr = 677.32Dx = 1.554 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybcCell parameters from 23915 reflections
a = 13.9118 (3) Åθ = 3.0–27.5°
b = 10.37486 (19) ŵ = 1.10 mm1
c = 20.6696 (4) ÅT = 173 K
β = 103.9290 (7)°Prism, orange
V = 2895.58 (10) Å30.29 × 0.16 × 0.09 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5991 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.026
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
h = 1816
Tmin = 0.653, Tmax = 0.906k = 1313
27863 measured reflectionsl = 2626
6611 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.055H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.030P)2 + 0.7505P]
where P = (Fo2 + 2Fc2)/3
6611 reflections(Δ/σ)max = 0.002
318 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = 0.41 e Å3
Primary atom site location: structure-invariant direct methods
Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pd10.445690 (8)0.127519 (11)0.438647 (5)0.01874 (4)
S10.23361 (3)0.07069 (4)0.62208 (2)0.02695 (9)
S20.33076 (3)0.01477 (4)0.380204 (19)0.02739 (9)
S30.16917 (3)0.14420 (4)0.42171 (2)0.03236 (10)
S40.62982 (3)0.20479 (4)0.243916 (18)0.02268 (8)
S50.55236 (3)0.28483 (4)0.491361 (18)0.02711 (9)
S60.69939 (3)0.43033 (4)0.44191 (2)0.02856 (9)
N10.36382 (9)0.11220 (12)0.50727 (6)0.0212 (3)
N20.28481 (9)0.02514 (13)0.49893 (6)0.0230 (3)
N30.52642 (9)0.14181 (12)0.36967 (6)0.0199 (3)
N40.59676 (9)0.23996 (12)0.37280 (6)0.0210 (3)
C10.23047 (13)0.13519 (17)0.69779 (8)0.0299 (4)
C20.29897 (12)0.22996 (17)0.71778 (8)0.0291 (4)
C30.35536 (11)0.25145 (16)0.67058 (8)0.0257 (3)
C40.32909 (11)0.17267 (15)0.61530 (7)0.0215 (3)
C50.37951 (11)0.17795 (15)0.56243 (7)0.0229 (3)
C60.26694 (11)0.03421 (15)0.44212 (8)0.0236 (3)
C70.12317 (12)0.14223 (16)0.49665 (8)0.0282 (4)
C80.03196 (12)0.22856 (17)0.48830 (8)0.0308 (4)
C90.00963 (12)0.22185 (16)0.54994 (8)0.0289 (4)
C100.10092 (12)0.30552 (17)0.54594 (8)0.0288 (4)
C110.14158 (12)0.29491 (17)0.60786 (8)0.0306 (4)
C120.23029 (14)0.38193 (19)0.60570 (9)0.0371 (4)
C130.62530 (12)0.14409 (16)0.16608 (8)0.0253 (4)
C140.57282 (11)0.03198 (16)0.15376 (7)0.0254 (4)
C150.53452 (11)0.00569 (15)0.20800 (7)0.0225 (3)
C160.55806 (10)0.07908 (14)0.26131 (7)0.0198 (3)
C170.51565 (10)0.06760 (14)0.31758 (7)0.0205 (3)
C180.61180 (10)0.30603 (14)0.42768 (7)0.0206 (3)
C190.74920 (12)0.42087 (16)0.36876 (8)0.0263 (4)
C200.83901 (11)0.50861 (16)0.37627 (8)0.0251 (3)
C210.87886 (12)0.49949 (17)0.31384 (8)0.0288 (4)
C220.96919 (12)0.58270 (16)0.31514 (9)0.0292 (4)
C231.00835 (13)0.56552 (19)0.25291 (9)0.0363 (4)
C241.09925 (15)0.6467 (2)0.25375 (11)0.0456 (5)
H10.18570.10780.72320.0359*
H20.30760.27590.75850.0350*
H30.40650.31410.67630.0308*
H40.43220.23850.56860.0275*
H50.17560.17280.53490.0339*
H60.10570.05290.50620.0339*
H70.01930.20060.44870.0370*
H80.05020.31870.48100.0370*
H90.02680.13120.55700.0347*
H100.04260.24880.58920.0347*
H110.15310.27960.50640.0346*
H120.08370.39660.53980.0346*
H130.08840.31730.64750.0367*
H140.16110.20440.61290.0367*
H150.25280.37110.64680.0446*
H160.21120.47190.60160.0446*
H170.28400.35880.56730.0446*
H180.65600.18420.13490.0304*
H190.56330.01520.11330.0305*
H200.49640.08160.20810.0270*
H210.47350.00470.31690.0247*
H220.76860.33080.36240.0316*
H230.69770.44680.32890.0316*
H240.89100.48240.41580.0301*
H250.82000.59870.38280.0301*
H260.89610.40850.30750.0345*
H270.82560.52460.27480.0345*
H281.02210.56020.35490.0350*
H290.95160.67430.31910.0350*
H301.02490.47360.24870.0436*
H310.95550.58880.21330.0436*
H321.11790.63700.21120.0547*
H331.15410.61810.29020.0547*
H341.08450.73740.26040.0547*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.01981 (7)0.02133 (7)0.01718 (6)0.00101 (4)0.00858 (4)0.00159 (4)
S10.0259 (2)0.0329 (3)0.02521 (19)0.00608 (15)0.01238 (15)0.00006 (16)
S20.0307 (2)0.0315 (2)0.02352 (18)0.00874 (16)0.01346 (15)0.00467 (16)
S30.0328 (3)0.0377 (3)0.0294 (2)0.01495 (17)0.01304 (17)0.00597 (17)
S40.02522 (19)0.02514 (18)0.02030 (17)0.00390 (14)0.01060 (14)0.00137 (14)
S50.0295 (2)0.0363 (3)0.01867 (17)0.01023 (16)0.01195 (15)0.00412 (15)
S60.0302 (2)0.0334 (3)0.02520 (19)0.01151 (16)0.01289 (15)0.00660 (16)
N10.0205 (7)0.0242 (7)0.0208 (6)0.0019 (5)0.0088 (5)0.0025 (5)
N20.0218 (7)0.0257 (7)0.0238 (7)0.0040 (5)0.0099 (5)0.0003 (5)
N30.0207 (7)0.0215 (7)0.0192 (6)0.0007 (5)0.0080 (5)0.0022 (5)
N40.0210 (7)0.0226 (7)0.0215 (6)0.0029 (5)0.0093 (5)0.0008 (5)
C10.0302 (9)0.0379 (10)0.0258 (8)0.0018 (7)0.0152 (7)0.0048 (7)
C20.0328 (9)0.0345 (9)0.0226 (8)0.0041 (7)0.0114 (7)0.0009 (7)
C30.0246 (8)0.0290 (9)0.0246 (8)0.0001 (6)0.0081 (6)0.0002 (7)
C40.0186 (8)0.0254 (8)0.0220 (7)0.0002 (6)0.0077 (6)0.0037 (6)
C50.0202 (8)0.0266 (8)0.0235 (7)0.0020 (6)0.0084 (6)0.0018 (6)
C60.0216 (8)0.0251 (8)0.0257 (8)0.0015 (6)0.0090 (6)0.0025 (6)
C70.0270 (9)0.0329 (9)0.0270 (8)0.0065 (7)0.0109 (7)0.0008 (7)
C80.0265 (9)0.0356 (10)0.0316 (9)0.0094 (7)0.0095 (7)0.0006 (7)
C90.0272 (9)0.0296 (9)0.0312 (9)0.0047 (7)0.0096 (7)0.0012 (7)
C100.0249 (9)0.0336 (9)0.0292 (8)0.0042 (7)0.0087 (7)0.0025 (7)
C110.0285 (9)0.0339 (9)0.0315 (9)0.0017 (7)0.0113 (7)0.0026 (7)
C120.0330 (10)0.0471 (12)0.0355 (10)0.0070 (8)0.0162 (8)0.0038 (8)
C130.0263 (9)0.0325 (9)0.0197 (7)0.0015 (6)0.0107 (6)0.0005 (6)
C140.0248 (8)0.0314 (9)0.0210 (7)0.0036 (6)0.0074 (6)0.0051 (7)
C150.0216 (8)0.0216 (8)0.0251 (8)0.0016 (6)0.0072 (6)0.0021 (6)
C160.0186 (7)0.0220 (8)0.0198 (7)0.0009 (6)0.0066 (6)0.0008 (6)
C170.0200 (8)0.0209 (7)0.0221 (7)0.0005 (6)0.0078 (6)0.0020 (6)
C180.0201 (8)0.0247 (8)0.0181 (7)0.0005 (6)0.0071 (6)0.0025 (6)
C190.0263 (9)0.0317 (9)0.0239 (8)0.0073 (7)0.0119 (6)0.0033 (7)
C200.0226 (8)0.0268 (8)0.0269 (8)0.0036 (6)0.0083 (6)0.0009 (7)
C210.0270 (9)0.0334 (9)0.0286 (8)0.0058 (7)0.0119 (7)0.0010 (7)
C220.0264 (9)0.0294 (9)0.0345 (9)0.0022 (7)0.0127 (7)0.0040 (7)
C230.0327 (10)0.0436 (11)0.0360 (10)0.0010 (8)0.0150 (8)0.0083 (8)
C240.0421 (12)0.0488 (12)0.0538 (13)0.0033 (9)0.0271 (10)0.0131 (10)
Geometric parameters (Å, º) top
Pd1—S22.2946 (4)C22—C231.523 (3)
Pd1—S52.2966 (4)C23—C241.516 (3)
Pd1—N12.0278 (14)C1—H10.950
Pd1—N32.0216 (14)C2—H20.950
S1—C11.7122 (18)C3—H30.950
S1—C41.7300 (17)C5—H40.950
S2—C61.7360 (19)C7—H50.990
S3—C61.7475 (16)C7—H60.990
S3—C71.8129 (19)C8—H70.990
S4—C131.7147 (18)C8—H80.990
S4—C161.7320 (16)C9—H90.990
S5—C181.7288 (17)C9—H100.990
S6—C181.7498 (15)C10—H110.990
S6—C191.8112 (19)C10—H120.990
N1—N21.4009 (18)C11—H130.990
N1—C51.3012 (19)C11—H140.990
N2—C61.296 (2)C12—H150.980
N3—N41.4029 (18)C12—H160.980
N3—C171.3026 (19)C12—H170.980
N4—C181.2985 (19)C13—H180.950
C1—C21.362 (3)C14—H190.950
C2—C31.409 (3)C15—H200.950
C3—C41.381 (3)C17—H210.950
C4—C51.435 (3)C19—H220.990
C7—C81.529 (3)C19—H230.990
C8—C91.522 (3)C20—H240.990
C9—C101.524 (3)C20—H250.990
C10—C111.523 (3)C21—H260.990
C11—C121.521 (3)C21—H270.990
C13—C141.364 (3)C22—H280.990
C14—C151.408 (3)C22—H290.990
C15—C161.386 (2)C23—H300.990
C16—C171.430 (3)C23—H310.990
C19—C201.523 (3)C24—H320.980
C20—C211.525 (3)C24—H330.980
C21—C221.520 (3)C24—H340.980
S1···N13.3418 (15)C22···H13iii3.2117
S1···N22.8431 (15)C22···H16iii3.5813
S1···C73.4705 (16)C23···H1xvi3.2288
S2···C173.2595 (16)C23···H13iii3.3178
S4···N33.3245 (15)C23···H13xvi3.4597
S4···N42.8340 (14)C23···H14xvi3.5676
S4···C193.5184 (16)C24···H1xvi3.0297
S5···C53.2970 (17)C24···H10xvi3.4675
N2···C42.792 (2)C24···H13xvi3.4659
N2···C72.833 (3)C24···H16iii3.5220
N4···C162.7909 (19)C24···H26xvii3.0049
N4···C192.848 (3)H1···C12xiv3.4422
C5···C63.407 (2)H1···C23x3.2288
C17···C183.409 (2)H1···C24x3.0297
S5···C13i3.5849 (17)H1···H13xiv3.3644
N4···C15ii3.4088 (19)H1···H15xiv2.6333
C2···C15iii3.380 (3)H1···H29ix2.9526
C3···C15i3.583 (3)H1···H30x2.5613
C3···C16i3.466 (2)H1···H32x2.6989
C4···C17iii3.371 (2)H1···H33x2.8102
C12···C14iv3.496 (3)H2···S2i3.4900
C13···S5v3.5849 (17)H2···N3i3.4500
C14···C12vi3.496 (3)H2···C15iii3.5252
C14···C18vii3.584 (2)H2···C17i3.2861
C15···N4vii3.4088 (19)H2···C21ix3.5401
C15···C2iii3.380 (3)H2···H15xiv2.7305
C15···C3v3.583 (3)H2···H20iii3.3270
C16···C3v3.466 (2)H2···H21i3.3273
C17···C4iii3.371 (2)H2···H23ix3.3893
C18···C14ii3.584 (2)H2···H25ix3.2994
Pd1···H42.9696H2···H27ix2.7526
Pd1···H212.9724H3···S4i3.0909
S1···H23.4858H3···C13i3.1313
S1···H33.4814H3···C14i2.9389
S1···H53.0957H3···C15i2.6439
S1···H62.9150H3···C16i2.6419
S2···H212.6304H3···C17i3.1953
S3···H72.8693H3···C19ix3.4854
S3···H82.9142H3···H19i3.4877
S4···H193.4855H3···H20iii3.4360
S4···H203.4875H3···H20i3.0498
S4···H223.0257H3···H21i3.4528
S4···H233.0792H3···H23ix2.8625
S5···H42.6192H3···H25ix3.2225
S6···H242.8956H4···C13i3.1867
S6···H252.8886H4···C14i3.3075
N2···H43.1232H4···H17viii3.3036
N2···H52.7608H4···H18i3.1878
N2···H62.6580H4···H19i3.4071
N4···H213.1249H4···H21iii3.4222
N4···H222.6265H5···S6iii3.1605
N4···H232.8304H5···N4iii3.3533
C1···H33.1885H5···C18iii3.1863
C3···H13.1958H5···C19iii3.2680
C3···H42.5861H5···H22iii2.6473
C4···H13.3984H5···H24iii3.5593
C4···H23.2291H6···C8viii3.5089
C5···H32.6918H6···C9viii3.2418
C6···H52.9209H6···H6viii3.0917
C6···H62.8724H6···H7viii3.1253
C7···H92.6794H6···H9viii2.4221
C7···H102.6776H6···H11viii3.5336
C8···H112.7413H7···S1viii3.2784
C8···H122.7544H7···C22xi3.5349
C9···H52.7172H7···H6viii3.1253
C9···H62.6768H7···H9viii3.5087
C9···H132.7042H7···H24xi3.5259
C9···H142.7367H7···H25xi3.1185
C10···H72.7585H7···H28xi3.2850
C10···H82.7570H7···H29xi2.9169
C10···H153.3757H8···C20iii3.5745
C10···H162.7405H8···C22xi3.4935
C10···H172.7438H8···H12xviii3.0374
C11···H92.7101H8···H22iii3.5959
C11···H102.7236H8···H24xi3.0889
C12···H112.7475H8···H24iii2.6960
C12···H122.7152H8···H25xi3.4608
C13···H203.1943H8···H28xi2.8339
C15···H183.2011H8···H29xi3.2971
C15···H212.5893H9···S3viii3.5632
C16···H183.4035H9···C7viii3.2183
C16···H193.2289H9···H6viii2.4221
C17···H202.7017H9···H7viii3.5087
C18···H222.8400H9···H31x3.3269
C18···H232.9836H9···H32x3.3361
C19···H262.6525H10···C19iii3.3349
C19···H272.6549H10···C20iii3.1501
C20···H282.7408H10···C21iii3.3050
C20···H292.7747H10···C24x3.4675
C21···H222.6760H10···H22iii2.7133
C21···H232.6696H10···H24iii2.6043
C21···H302.7073H10···H26iii2.6746
C21···H312.7173H10···H31x3.5067
C22···H242.7716H10···H32x2.7450
C22···H252.7736H10···H34x3.4467
C22···H323.3693H11···S1viii3.4028
C22···H332.7665H11···N1viii3.3602
C22···H342.7033H11···N2viii3.2004
C23···H262.6868H11···C4viii3.2546
C23···H272.7217H11···C5viii3.3018
C24···H282.7215H11···C20xi3.4550
C24···H292.7313H11···H6viii3.5336
H1···H22.4205H11···H24xi3.2465
H2···H32.4633H11···H25xi2.7928
H3···H42.4651H12···C20xi3.4358
H5···H72.8775H12···C22iii3.5990
H5···H82.3749H12···H8xviii3.0374
H5···H92.9917H12···H24xi2.8004
H5···H102.5112H12···H24iii2.7630
H6···H72.4055H12···H25xi3.1993
H6···H82.8773H12···H26iii3.5798
H6···H92.4695H12···H28iii2.7303
H6···H102.9278H13···C21iii3.4046
H7···H92.3769H13···C22iii3.2117
H7···H102.8659H13···C23iii3.3178
H7···H112.5749H13···C23x3.4597
H7···H123.0488H13···C24x3.4659
H8···H92.8660H13···H1xv3.3644
H8···H102.3779H13···H26iii2.7793
H8···H113.0261H13···H28iii2.6889
H8···H122.5874H13···H30iii2.6645
H9···H112.3801H13···H31x2.7275
H9···H122.8629H13···H32x3.4140
H9···H132.9547H13···H33iii3.5777
H9···H142.5379H13···H34x3.0357
H10···H112.8629H14···S2viii3.3048
H10···H122.3694H14···N1viii3.4150
H10···H132.5174H14···N2viii3.1380
H10···H143.0255H14···C6viii2.9635
H11···H132.8634H14···C23x3.5676
H11···H142.3623H14···H31x2.5993
H11···H163.0448H15···C1xv3.1528
H11···H172.5836H15···C2xv3.1957
H12···H132.3883H15···C13iv3.3734
H12···H142.8633H15···C14iv2.9762
H12···H162.5456H15···H1xv2.6333
H12···H173.0003H15···H2xv2.7305
H13···H152.3509H15···H18iv3.4739
H13···H162.3687H15···H19iv2.7505
H13···H172.8573H15···H30iii3.5427
H14···H152.3535H15···H33iii3.0479
H14···H162.8573H16···S6xi3.3910
H14···H172.3662H16···C13iv3.4054
H18···H192.4215H16···C14iv3.4837
H19···H202.4607H16···C22iii3.5813
H20···H212.4778H16···C24iii3.5220
H22···H242.3848H16···H18iv3.0573
H22···H252.8757H16···H19iv3.2074
H22···H262.4585H16···H28iii2.7255
H22···H272.9381H16···H30iii3.5247
H23···H242.8758H16···H33iii2.6597
H23···H252.3896H17···Pd1viii3.2712
H23···H262.9249H17···S6xi3.3568
H23···H272.4542H17···N1viii3.0547
H24···H262.3816H17···C5viii3.2805
H24···H272.8690H17···C14iv3.4790
H24···H282.5819H17···H4viii3.3036
H24···H293.0793H17···H19iv2.8466
H25···H262.8688H18···S2ii3.1489
H25···H272.3798H18···S3ii3.4390
H25···H283.0302H18···S5v2.9879
H25···H292.6205H18···H4v3.1878
H26···H282.3841H18···H15vi3.4739
H26···H292.8586H18···H16vi3.0573
H26···H302.4895H18···H33xii2.8069
H26···H312.9591H19···S5vii3.1461
H27···H282.8588H19···S5v3.4501
H27···H292.3564H19···N4vii3.4351
H27···H302.9976H19···C12vi3.1035
H27···H312.5375H19···C18vii3.0160
H28···H302.3806H19···H3v3.4877
H28···H312.8650H19···H4v3.4071
H28···H332.5885H19···H15vi2.7505
H28···H342.9610H19···H16vi3.2074
H29···H302.8649H19···H17vi2.8466
H29···H312.3728H20···S4vii3.1330
H29···H323.5998H20···N3vii3.2668
H29···H333.0721H20···N4vii2.6186
H29···H342.5301H20···C2iii3.2749
H30···H322.3730H20···C3iii3.3409
H30···H332.3387H20···C18vii3.0763
H30···H342.8534H20···C19vii3.4030
H31···H322.3244H20···H2iii3.3270
H31···H332.8523H20···H3iii3.4360
H31···H342.3883H20···H3v3.0498
Pd1···H17viii3.2712H20···H23vii2.6390
S1···H7viii3.2784H21···S4vii3.4439
S1···H11viii3.4028H21···C3iii3.4632
S1···H25ix3.5060H21···C4iii3.2699
S1···H32x3.4718H21···C5iii3.3439
S2···H2v3.4900H21···H2v3.3273
S2···H14viii3.3048H21···H3v3.4528
S2···H18vii3.1489H21···H4iii3.4222
S2···H27vii3.4367H21···H23vii3.3985
S3···H9viii3.5632H22···C7iii3.5324
S3···H18vii3.4390H22···C9iii3.5893
S3···H34xi3.4824H22···H5iii2.6473
S4···H3v3.0909H22···H8iii3.5959
S4···H20ii3.1330H22···H10iii2.7133
S4···H21ii3.4439H22···H32xii3.1633
S4···H32xii3.4790H23···C2ix3.4935
S4···H33xii3.3714H23···C3ix3.2174
S5···H18i2.9879H23···C15ii3.1741
S5···H19ii3.1461H23···H2ix3.3893
S5···H19i3.4501H23···H3ix2.8625
S6···H5iii3.1605H23···H20ii2.6390
S6···H16xiii3.3910H23···H21ii3.3985
S6···H17xiii3.3568H24···C8iii3.3152
N1···H11viii3.3602H24···C9iii3.1571
N1···H14viii3.4150H24···C10xiii3.4566
N1···H17viii3.0547H24···C10iii3.3774
N2···H11viii3.2004H24···H5iii3.5593
N2···H14viii3.1380H24···H7xiii3.5259
N3···H2v3.4500H24···H8xiii3.0889
N3···H20ii3.2668H24···H8iii2.6960
N4···H5iii3.3533H24···H10iii2.6043
N4···H19ii3.4351H24···H11xiii3.2465
N4···H20ii2.6186H24···H12xiii2.8004
C1···H15xiv3.1528H24···H12iii2.7630
C1···H25ix3.2136H25···S1ix3.5060
C1···H29ix3.1652H25···C1ix3.2136
C1···H30x3.4653H25···C2ix2.9267
C1···H32x3.2726H25···C3ix2.8789
C1···H33x3.5584H25···C4ix3.1567
C2···H15xiv3.1957H25···C10xiii3.4317
C2···H20iii3.2749H25···H2ix3.2994
C2···H23ix3.4935H25···H3ix3.2225
C2···H25ix2.9267H25···H7xiii3.1185
C2···H27ix3.1038H25···H8xiii3.4608
C2···H29ix3.5271H25···H11xiii2.7928
C3···H20iii3.3409H25···H12xiii3.1993
C3···H21iii3.4632H26···C9iii3.5613
C3···H23ix3.2174H26···C24xii3.0049
C3···H25ix2.8789H26···H10iii2.6746
C4···H11viii3.2546H26···H12iii3.5798
C4···H21iii3.2699H26···H13iii2.7793
C4···H25ix3.1567H26···H32xii2.8442
C5···H11viii3.3018H26···H34xii2.3188
C5···H17viii3.2805H27···S2ii3.4367
C5···H21iii3.3439H27···C2ix3.1038
C6···H14viii2.9635H27···H2ix2.7526
C7···H9viii3.2183H27···H34xii3.3783
C7···H22iii3.5324H28···C8xiii3.4988
C8···H6viii3.5089H28···C10iii3.3624
C8···H24iii3.3152H28···C11iii3.2120
C8···H28xi3.4988H28···C12iii3.3673
C8···H29xi3.5517H28···H7xiii3.2850
C9···H6viii3.2418H28···H8xiii2.8339
C9···H22iii3.5893H28···H12iii2.7303
C9···H24iii3.1571H28···H13iii2.6889
C9···H26iii3.5613H28···H16iii2.7255
C9···H32x3.4914H29···C1ix3.1652
C10···H24xi3.4566H29···C2ix3.5271
C10···H24iii3.3774H29···C8xiii3.5517
C10···H25xi3.4317H29···H1ix2.9526
C10···H28iii3.3624H29···H7xiii2.9169
C11···H28iii3.2120H29···H8xiii3.2971
C11···H30iii3.5414H29···H30xvii3.4539
C11···H31x3.1188H30···C1xvi3.4653
C12···H1xv3.4422H30···C11iii3.5414
C12···H19iv3.1035H30···H1xvi2.5613
C12···H28iii3.3673H30···H13iii2.6645
C12···H33iii3.2650H30···H15iii3.5427
C13···H3v3.1313H30···H16iii3.5247
C13···H4v3.1867H30···H29xii3.4539
C13···H15vi3.3734H30···H34xii2.8670
C13···H16vi3.4054H31···C11xvi3.1188
C13···H33xii2.9959H31···H9xvi3.3269
C14···H3v2.9389H31···H10xvi3.5067
C14···H4v3.3075H31···H13xvi2.7275
C14···H15vi2.9762H31···H14xvi2.5993
C14···H16vi3.4837H32···S1xvi3.4718
C14···H17vi3.4790H32···S4xvii3.4790
C15···H2iii3.5252H32···C1xvi3.2726
C15···H3v2.6439H32···C9xvi3.4914
C15···H23vii3.1741H32···H1xvi2.6989
C16···H3v2.6419H32···H9xvi3.3361
C17···H2v3.2861H32···H10xvi2.7450
C17···H3v3.1953H32···H13xvi3.4140
C18···H5iii3.1863H32···H22xvii3.1633
C18···H19ii3.0160H32···H26xvii2.8442
C18···H20ii3.0763H33···S4xvii3.3714
C19···H3ix3.4854H33···C1xvi3.5584
C19···H5iii3.2680H33···C12iii3.2650
C19···H10iii3.3349H33···C13xvii2.9959
C19···H20ii3.4030H33···H1xvi2.8102
C20···H8iii3.5745H33···H13iii3.5777
C20···H10iii3.1501H33···H15iii3.0479
C20···H11xiii3.4550H33···H16iii2.6597
C20···H12xiii3.4358H33···H18xvii2.8069
C21···H2ix3.5401H34···S3xiii3.4824
C21···H10iii3.3050H34···C21xvii3.2219
C21···H13iii3.4046H34···H10xvi3.4467
C21···H34xii3.2219H34···H13xvi3.0357
C22···H7xiii3.5349H34···H26xvii2.3188
C22···H8xiii3.4935H34···H27xvii3.3783
C22···H12iii3.5990H34···H30xvii2.8670
S2—Pd1—S5174.706 (15)C7—C8—H8109.534
S2—Pd1—N183.13 (4)C9—C8—H7109.539
S2—Pd1—N396.37 (4)C9—C8—H8109.538
S5—Pd1—N197.55 (4)H7—C8—H8108.094
S5—Pd1—N382.95 (4)C8—C9—H9108.735
N1—Pd1—N3179.49 (5)C8—C9—H10108.728
C1—S1—C491.38 (9)C10—C9—H9108.723
Pd1—S2—C695.85 (5)C10—C9—H10108.731
C6—S3—C7101.58 (8)H9—C9—H10107.649
C13—S4—C1691.46 (8)C9—C10—H11109.041
Pd1—S5—C1895.86 (5)C9—C10—H12109.039
C18—S6—C19102.16 (8)C11—C10—H11109.048
Pd1—N1—N2121.37 (10)C11—C10—H12109.046
Pd1—N1—C5124.60 (11)H11—C10—H12107.808
N2—N1—C5114.02 (14)C10—C11—H13108.912
N1—N2—C6113.05 (14)C10—C11—H14108.907
Pd1—N3—N4121.36 (10)C12—C11—H13108.921
Pd1—N3—C17124.52 (11)C12—C11—H14108.922
N4—N3—C17114.04 (13)H13—C11—H14107.746
N3—N4—C18112.79 (13)C11—C12—H15109.461
S1—C1—C2112.92 (15)C11—C12—H16109.469
C1—C2—C3111.69 (16)C11—C12—H17109.480
C2—C3—C4113.50 (15)H15—C12—H16109.467
S1—C4—C3110.51 (13)H15—C12—H17109.471
S1—C4—C5127.64 (12)H16—C12—H17109.479
C3—C4—C5121.82 (15)S4—C13—H18123.669
N1—C5—C4129.63 (15)C14—C13—H18123.665
S2—C6—S3113.85 (9)C13—C14—H19123.956
S2—C6—N2126.31 (13)C15—C14—H19123.944
S3—C6—N2119.83 (14)C14—C15—H20123.386
S3—C7—C8110.55 (11)C16—C15—H20123.364
C7—C8—C9110.55 (14)N3—C17—H21115.283
C8—C9—C10114.09 (14)C16—C17—H21115.291
C9—C10—C11112.74 (14)S6—C19—H22109.524
C10—C11—C12113.29 (14)S6—C19—H23109.519
S4—C13—C14112.67 (14)C20—C19—H22109.527
C13—C14—C15112.10 (14)C20—C19—H23109.533
C14—C15—C16113.25 (14)H22—C19—H23108.099
S4—C16—C15110.52 (12)C19—C20—H24109.789
S4—C16—C17127.07 (11)C19—C20—H25109.788
C15—C16—C17121.93 (14)C21—C20—H24109.784
N3—C17—C16129.43 (14)C21—C20—H25109.775
S5—C18—S6114.03 (8)H24—C20—H25108.238
S5—C18—N4126.29 (12)C20—C21—H26108.594
S6—C18—N4119.68 (13)C20—C21—H27108.600
S6—C19—C20110.60 (12)C22—C21—H26108.603
C19—C20—C21109.45 (13)C22—C21—H27108.597
C20—C21—C22114.67 (14)H26—C21—H27107.562
C21—C22—C23112.39 (14)C21—C22—H28109.116
C22—C23—C24113.10 (16)C21—C22—H29109.120
S1—C1—H1123.545C23—C22—H28109.128
C2—C1—H1123.538C23—C22—H29109.124
C1—C2—H2124.148H28—C22—H29107.857
C3—C2—H2124.162C22—C23—H30108.950
C2—C3—H3123.244C22—C23—H31108.957
C4—C3—H3123.254C24—C23—H30108.964
N1—C5—H4115.179C24—C23—H31108.970
C4—C5—H4115.195H30—C23—H31107.768
S3—C7—H5109.538C23—C24—H32109.466
S3—C7—H6109.533C23—C24—H33109.479
C8—C7—H5109.539C23—C24—H34109.476
C8—C7—H6109.535H32—C24—H33109.469
H5—C7—H6108.101H32—C24—H34109.466
C7—C8—H7109.541H33—C24—H34109.471
S2—Pd1—N1—N25.37 (8)N2—N1—C5—C40.9 (2)
S2—Pd1—N1—C5175.96 (9)C5—N1—N2—C6176.43 (11)
N1—Pd1—S2—C63.71 (4)N1—N2—C6—S20.40 (19)
S2—Pd1—N3—N4166.01 (8)N1—N2—C6—S3178.57 (10)
S2—Pd1—N3—C1710.48 (9)Pd1—N3—N4—C188.32 (14)
N3—Pd1—S2—C6176.34 (4)Pd1—N3—C17—C16170.50 (9)
S5—Pd1—N1—N2179.93 (8)N4—N3—C17—C166.22 (19)
S5—Pd1—N1—C51.25 (9)C17—N3—N4—C18174.84 (11)
N1—Pd1—S5—C18174.28 (4)N3—N4—C18—S51.78 (18)
S5—Pd1—N3—N48.71 (8)N3—N4—C18—S6178.39 (9)
S5—Pd1—N3—C17174.80 (9)S1—C1—C2—C30.21 (18)
N3—Pd1—S5—C185.62 (4)C1—C2—C3—C40.05 (19)
C1—S1—C4—C30.20 (11)C2—C3—C4—S10.12 (17)
C1—S1—C4—C5178.48 (13)C2—C3—C4—C5178.52 (12)
C4—S1—C1—C20.24 (12)S1—C4—C5—N12.6 (3)
Pd1—S2—C6—S3177.88 (7)C3—C4—C5—N1179.33 (14)
Pd1—S2—C6—N23.09 (13)S3—C7—C8—C9177.26 (9)
C6—S3—C7—C8177.07 (9)C7—C8—C9—C10179.89 (12)
C7—S3—C6—S2178.73 (9)C8—C9—C10—C11179.07 (12)
C7—S3—C6—N22.17 (13)C9—C10—C11—C12177.74 (12)
C13—S4—C16—C150.99 (10)S4—C13—C14—C150.50 (17)
C13—S4—C16—C17171.07 (11)C13—C14—C15—C160.27 (18)
C16—S4—C13—C140.86 (11)C14—C15—C16—S40.90 (16)
Pd1—S5—C18—S6175.85 (7)C14—C15—C16—C17171.64 (12)
Pd1—S5—C18—N43.99 (12)S4—C16—C17—N35.3 (2)
C18—S6—C19—C20171.22 (9)C15—C16—C17—N3176.58 (13)
C19—S6—C18—S5177.78 (8)S6—C19—C20—C21179.57 (9)
C19—S6—C18—N42.37 (12)C19—C20—C21—C22179.85 (12)
Pd1—N1—N2—C64.76 (15)C20—C21—C22—C23177.59 (12)
Pd1—N1—C5—C4177.83 (9)C21—C22—C23—C24179.31 (12)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y+1/2, z+1/2; (iii) x+1, y, z+1; (iv) x1, y1/2, z+1/2; (v) x, y+1/2, z1/2; (vi) x+1, y1/2, z1/2; (vii) x+1, y1/2, z+1/2; (viii) x, y, z+1; (ix) x+1, y+1, z+1; (x) x1, y+1/2, z+1/2; (xi) x1, y1, z; (xii) x+2, y1/2, z+1/2; (xiii) x+1, y+1, z; (xiv) x, y+1/2, z+3/2; (xv) x, y1/2, z+3/2; (xvi) x+1, y+1/2, z1/2; (xvii) x+2, y+1/2, z+1/2; (xviii) x, y1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H4···S50.952.623.2970 (17)129
C15—H20···N4vii0.952.623.4088 (19)141
C17—H21···S20.952.633.2596 (16)124
Symmetry code: (vii) x+1, y1/2, z+1/2.
 

Acknowledgements

MSB is grateful to the Department of Chemistry, Rajshahi University, for the provision of laboratory facilities. MCS acknowledges the Department of Applied Chemistry, Toyama University, for providing funds for single-crystal X-ray analyses.

References

First citationAltomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  CrossRef Web of Science IUCr Journals Google Scholar
First citationBegum, M. S., Howlader, M. B. H., Miyatake, R., Zangrando, E. & Sheikh, M. C. (2015). Acta Cryst. E71, o199.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBegum, M. S., Zangrando, E., Howlader, M. B. H., Sheikh, M. C., Miyatake, R., Hossain, M. M., Alam, M. M. & Hasnat, M. A. (2016). Polyhedron, 105, 56–61.  CSD CrossRef CAS Google Scholar
First citationBegum, M. S., Zangrando, E., Sheikh, M. C., Miyatake, R. & Hossain, M. M. (2015). Acta Cryst. E71, o265–o266.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationRigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (2010). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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