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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 8| August 2012| Page o2307
https://doi.org/10.1107/S160053681202925X

3-Acetyl-1-(2,6-di­chloro­phen­yl)thio­urea

Sharatha Kumar,a Sabine Forob and B. Thimme Gowdaa*

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com

(Received 22 June 2012; accepted 27 June 2012; online 4 July 2012)

In the title compound, C9H8Cl2N2OS, the conformation of one of the N—H bonds is anti to the C=S group and the other is anti to the C=O group. Further, the conformations of the amide C=S and the C=O group are anti to each other. The 2,6-dichloro­phenyl ring and the 3-acetyl­thio­urea side chain are inclined to one another at a dihedral angle of 83.44 (5)°. An intra­molecular N—H⋯O hydrogen bond occurs. In the crystal, mol­ecules form inversion dimers through pairs of N—H⋯S hydrogen bonds.

Related literature

For studies of the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Bhat & Gowda (2000[Bhat, D. K. & Gowda, B. T. (2000). J. Indian Chem. Soc. 77, 279-284.]); Gowda et al. (2003[Gowda, B. T., Usha, K. M. & Jayalakshmi, K. L. (2003). Z. Naturforsch. Teil A, 58, 801-806.]); Shahwar et al. (2012[Shahwar, D., Tahir, M. N., Chohan, M. M., Ahmad, N. & Raza, M. A. (2012). Acta Cryst. E68, o1160.]), of N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007[Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2597.]) and of N-chloro­aryl­sulfonamides, see: Gowda et al. (2005[Gowda, B. T., Damodara, N. & Jyothi, K. (2005). Int. J. Chem. Kinet. 37, 572-582.]); Shetty & Gowda (2004[Shetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63-72.]).

[Scheme 1]

Experimental

Crystal data

  • C9H8Cl2N2OS

  • Mr = 263.13

  • Triclinic, [P \overline 1]

  • a = 7.729 (1) Å

  • b = 8.047 (1) Å

  • c = 10.015 (1) Å

  • α = 88.05 (1)°

  • β = 76.39 (1)°

  • γ = 66.57 (1)°

  • V = 554.24 (11) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.75 mm−1

  • T = 293 K

  • 0.44 × 0.44 × 0.04 mm
Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.735, Tmax = 0.971

  • 3638 measured reflections

  • 2232 independent reflections

  • 1930 reflections with I > 2σ(I)

  • Rint = 0.013
Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.095

  • S = 1.09

  • 2232 reflections

  • 143 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O1 0.84 (2) 1.94 (2) 2.631 (2) 139 (2)
N2—H2N⋯S1i 0.85 (2) 2.63 (2) 3.4252 (17) 158 (2)
Symmetry code: (i) -x, -y+2, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681202925X/sj5247sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681202925X/sj5247Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681202925X/sj5247Isup3.cml

checkCIF report


Comment top

Thiourea and its derivatives exhibit a wide variety of biological activities. As part of our studies of the substituent effects on the structures and other aspects of N-(aryl)-amides (Bhat & Gowda, 2000); Gowda et al., 2003; Shahwar et al., 2012); N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-chloroarylsulfonamides (Gowda et al., 2005; Shetty & Gowda, 2004), in the present work, the crystal structure of 3-acetyl-1-(2,6-dichlorophenyl)thiourea has been determined (Fig. 1).

The conformations of the amide C═S and the C═O are anti to each other, similar to the anti conformation observed in 3-acetyl-1-(2-methylphenyl)thiourea (Shahwar et al., 2012). Further, the conformation of one of the N—H bonds is anti to the C═S and the other is anti to the C═O. The conformations of the two N—H bonds are are also anti to each other.

The side chain is tilted with respect to the 2,6-dichlorophenyl ring with torsion angles of C2—C1—N1—C7 = -86.22 (26)° and C6—C1—N1—C7 = 96.58 (24)°. The dihedral angle between the phenyl ring and the side chain is 83.44 (5)°.

The structure shows intramolecular hydrogen bonding between the NH hydrogen atom, attached to the 2,6-dichlorophenyl ring and the amide oxygen. In the crystal, the molecules form inversion type dimers through N—H···S intermolecular hydrogen bonds (Table 1, Fig.2).

Related literature top

For studies of the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bhat & Gowda (2000); Gowda et al. (2003); Shahwar et al. (2012), of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and of N-chloroarylsulfonamides, see: Gowda et al. (2005); Shetty & Gowda (2004).

Experimental top

3-Acetyl-1-(2,6-dichlorophenyl)-thiourea was synthesized by adding a solution of acetyl chloride (0.10 mol) in acetone (30 ml) dropwise to a suspension of ammonium thiocyanate (0.10 mol) in acetone (30 ml). The reaction mixture was refluxed for 30 min. After cooling to room temperature, a solution of 2,6-dichloroaniline (0.10 mol) in acetone (10 ml) was added and refluxed for 3 h. The reaction mixture was poured into acidified cold water. The precipitated title compound was recrystallized to constant melting point from acetonitrile. The purity of the compound was checked and characterized by its infrared spectrum.

Plate like dark yellow single crystals used in X-ray diffraction studies were grown in acetonitrile solution by slow evaporation of the solvent at room temperature.

Refinement top

H atoms bonded to C were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93 Å, methyl C—H = 0.96 Å. The amino H atoms were freely refined with the N—H distances restrained to 0.86 (2) Å. All H atoms were refined with isotropic displacement parameters set at 1.2 Ueq(C-aromatic, N) and 1.5 Ueq (C-methyl) of the parent atom.

Structure description top

Thiourea and its derivatives exhibit a wide variety of biological activities. As part of our studies of the substituent effects on the structures and other aspects of N-(aryl)-amides (Bhat & Gowda, 2000); Gowda et al., 2003; Shahwar et al., 2012); N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-chloroarylsulfonamides (Gowda et al., 2005; Shetty & Gowda, 2004), in the present work, the crystal structure of 3-acetyl-1-(2,6-dichlorophenyl)thiourea has been determined (Fig. 1).

The conformations of the amide C═S and the C═O are anti to each other, similar to the anti conformation observed in 3-acetyl-1-(2-methylphenyl)thiourea (Shahwar et al., 2012). Further, the conformation of one of the N—H bonds is anti to the C═S and the other is anti to the C═O. The conformations of the two N—H bonds are are also anti to each other.

The side chain is tilted with respect to the 2,6-dichlorophenyl ring with torsion angles of C2—C1—N1—C7 = -86.22 (26)° and C6—C1—N1—C7 = 96.58 (24)°. The dihedral angle between the phenyl ring and the side chain is 83.44 (5)°.

The structure shows intramolecular hydrogen bonding between the NH hydrogen atom, attached to the 2,6-dichlorophenyl ring and the amide oxygen. In the crystal, the molecules form inversion type dimers through N—H···S intermolecular hydrogen bonds (Table 1, Fig.2).

For studies of the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bhat & Gowda (2000); Gowda et al. (2003); Shahwar et al. (2012), of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and of N-chloroarylsulfonamides, see: Gowda et al. (2005); Shetty & Gowda (2004).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level. The intramolecular hydrogen bond is shown as a dashed line.
[Figure 2] Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
3-Acetyl-1-(2,6-dichlorophenyl)thiourea top
Crystal data top
C9H8Cl2N2OSZ = 2
Mr = 263.13F(000) = 268
Triclinic, P1Dx = 1.577 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.729 (1) ÅCell parameters from 2085 reflections
b = 8.047 (1) Åθ = 2.8–27.7°
c = 10.015 (1) ŵ = 0.75 mm−1
α = 88.05 (1)°T = 293 K
β = 76.39 (1)°Plate, dark yellow
γ = 66.57 (1)°0.44 × 0.44 × 0.04 mm
V = 554.24 (11) Å3
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2232 independent reflections
Radiation source: fine-focus sealed tube1930 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
Rotation method data acquisition using ω and phi scans.θmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		h = −9→9
Tmin = 0.735, Tmax = 0.971k = −10→9
3638 measured reflectionsl = −7→12
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0423P)2 + 0.2588P]
where P = (Fo2 + 2Fc2)/3
2232 reflections(Δ/σ)max = 0.005
143 parametersΔρmax = 0.30 e Å−3
3 restraintsΔρmin = −0.36 e Å−3
Crystal data top
C9H8Cl2N2OSγ = 66.57 (1)°
Mr = 263.13V = 554.24 (11) Å3
Triclinic, P1Z = 2
a = 7.729 (1) ÅMo Kα radiation
b = 8.047 (1) ŵ = 0.75 mm−1
c = 10.015 (1) ÅT = 293 K
α = 88.05 (1)°0.44 × 0.44 × 0.04 mm
β = 76.39 (1)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2232 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		1930 reflections with I > 2σ(I)
Tmin = 0.735, Tmax = 0.971Rint = 0.013
3638 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0373 restraints
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.30 e Å−3
2232 reflectionsΔρmin = −0.36 e Å−3
143 parameters
Special details top

Experimental. Absorption correction: CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0838 (3)0.5813 (3)0.14414 (19)0.0322 (4)
C20.2043 (3)0.5857 (3)0.0189 (2)0.0359 (5)
C30.3407 (3)0.4272 (3)−0.0553 (2)0.0447 (6)
H30.42180.4319−0.13890.054*
C40.3548 (3)0.2629 (3)−0.0042 (3)0.0488 (6)
H40.44660.1563−0.05370.059*
C50.2355 (4)0.2534 (3)0.1192 (3)0.0465 (6)
H50.24490.14160.15250.056*
C60.1012 (3)0.4131 (3)0.1927 (2)0.0374 (5)
C7−0.0252 (3)0.8408 (3)0.30587 (19)0.0300 (4)
C8−0.3676 (3)1.0659 (3)0.3506 (2)0.0356 (5)
C9−0.4980 (3)1.2494 (3)0.4221 (3)0.0524 (6)
H9A−0.45761.33970.37690.079*
H9B−0.49011.24900.51640.079*
H9C−0.62961.27680.41870.079*
N1−0.0603 (2)0.7439 (2)0.21891 (17)0.0342 (4)
H1N−0.175 (3)0.782 (3)0.210 (2)0.041*
N2−0.1818 (2)0.9960 (2)0.36945 (17)0.0349 (4)
H2N−0.156 (3)1.053 (3)0.426 (2)0.042*
O1−0.4216 (2)0.9862 (2)0.28007 (18)0.0530 (5)
Cl10.18527 (10)0.79226 (8)−0.04530 (6)0.05449 (19)
Cl2−0.04629 (11)0.40151 (9)0.34891 (6)0.0607 (2)
S10.19132 (8)0.78798 (8)0.33840 (6)0.04599 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0283 (9)0.0309 (10)0.0335 (10)−0.0061 (8)−0.0087 (8)−0.0104 (8)
C20.0328 (10)0.0362 (11)0.0355 (10)−0.0091 (9)−0.0099 (8)−0.0045 (8)
C30.0327 (11)0.0510 (14)0.0374 (11)−0.0048 (10)−0.0038 (9)−0.0144 (10)
C40.0393 (12)0.0385 (13)0.0534 (14)0.0040 (10)−0.0152 (11)−0.0198 (11)
C50.0501 (13)0.0290 (11)0.0562 (14)−0.0061 (10)−0.0214 (11)−0.0052 (10)
C60.0375 (11)0.0367 (11)0.0378 (11)−0.0129 (9)−0.0110 (9)−0.0062 (9)
C70.0291 (8)0.0289 (10)0.0276 (9)−0.0089 (8)−0.0025 (7)−0.0048 (8)
C80.0324 (10)0.0336 (11)0.0340 (10)−0.0077 (9)−0.0045 (8)−0.0046 (8)
C90.0411 (13)0.0410 (13)0.0574 (15)0.0012 (10)−0.0084 (11)−0.0153 (11)
N10.0258 (8)0.0321 (9)0.0393 (9)−0.0054 (7)−0.0070 (7)−0.0125 (7)
N20.0315 (9)0.0324 (9)0.0353 (9)−0.0067 (7)−0.0066 (7)−0.0131 (7)
O10.0351 (8)0.0514 (10)0.0654 (11)−0.0058 (7)−0.0162 (8)−0.0201 (8)
Cl10.0596 (4)0.0476 (4)0.0521 (4)−0.0206 (3)−0.0080 (3)0.0075 (3)
Cl20.0744 (5)0.0573 (4)0.0485 (4)−0.0325 (3)−0.0004 (3)0.0009 (3)
S10.0299 (3)0.0539 (4)0.0455 (3)−0.0060 (2)−0.0090 (2)−0.0226 (3)
Geometric parameters (Å, º) top
C1—C21.384 (3)C7—N11.329 (2)
C1—C61.388 (3)C7—N21.385 (2)
C1—N11.424 (2)C7—S11.664 (2)
C2—C31.384 (3)C8—O11.211 (2)
C2—Cl11.725 (2)C8—N21.376 (3)
C3—C41.374 (4)C8—C91.503 (3)
C3—H30.9300C9—H9A0.9600
C4—C51.377 (4)C9—H9B0.9600
C4—H40.9300C9—H9C0.9600
C5—C61.384 (3)N1—H1N0.836 (16)
C5—H50.9300N2—H2N0.845 (16)
C6—Cl21.730 (2)
C2—C1—C6118.15 (18)N1—C7—N2115.94 (17)
C2—C1—N1121.29 (19)N1—C7—S1124.10 (15)
C6—C1—N1120.50 (18)N2—C7—S1119.95 (14)
C1—C2—C3121.2 (2)O1—C8—N2122.41 (18)
C1—C2—Cl1119.41 (15)O1—C8—C9122.4 (2)
C3—C2—Cl1119.43 (18)N2—C8—C9115.21 (18)
C4—C3—C2119.3 (2)C8—C9—H9A109.5
C4—C3—H3120.4C8—C9—H9B109.5
C2—C3—H3120.4H9A—C9—H9B109.5
C3—C4—C5121.1 (2)C8—C9—H9C109.5
C3—C4—H4119.4H9A—C9—H9C109.5
C5—C4—H4119.4H9B—C9—H9C109.5
C4—C5—C6118.8 (2)C7—N1—C1123.48 (17)
C4—C5—H5120.6C7—N1—H1N116.3 (16)
C6—C5—H5120.6C1—N1—H1N120.3 (16)
C5—C6—C1121.4 (2)C8—N2—C7128.23 (17)
C5—C6—Cl2118.92 (18)C8—N2—H2N117.7 (16)
C1—C6—Cl2119.64 (15)C7—N2—H2N114.0 (16)
C6—C1—C2—C3−1.0 (3)N1—C1—C6—C5177.63 (19)
N1—C1—C2—C3−178.23 (18)C2—C1—C6—Cl2179.87 (15)
C6—C1—C2—Cl1179.45 (15)N1—C1—C6—Cl2−2.8 (3)
N1—C1—C2—Cl12.2 (3)N2—C7—N1—C1179.64 (19)
C1—C2—C3—C40.7 (3)S1—C7—N1—C10.7 (3)
Cl1—C2—C3—C4−179.70 (17)C2—C1—N1—C7−86.2 (3)
C2—C3—C4—C50.2 (3)C6—C1—N1—C796.6 (2)
C3—C4—C5—C6−0.8 (3)O1—C8—N2—C76.5 (4)
C4—C5—C6—C10.5 (3)C9—C8—N2—C7−172.7 (2)
C4—C5—C6—Cl2−179.01 (17)N1—C7—N2—C8−2.4 (3)
C2—C1—C6—C50.3 (3)S1—C7—N2—C8176.56 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.84 (2)1.94 (2)2.631 (2)139 (2)
N2—H2N···S1i0.85 (2)2.63 (2)3.4252 (17)158 (2)
Symmetry code: (i) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formulaC9H8Cl2N2OS
Mr263.13
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.729 (1), 8.047 (1), 10.015 (1)
α, β, γ (°)88.05 (1), 76.39 (1), 66.57 (1)
V (Å3)554.24 (11)
Z2
Radiation typeMo Kα
µ (mm−1)0.75
Crystal size (mm)0.44 × 0.44 × 0.04
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.735, 0.971
No. of measured, independent and
observed [I > 2σ(I)] reflections		3638, 2232, 1930
Rint0.013
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.095, 1.09
No. of reflections2232
No. of parameters143
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.30, −0.36

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.836 (16)1.94 (2)2.631 (2)139 (2)
N2—H2N···S1i0.845 (16)2.628 (17)3.4252 (17)158 (2)
Symmetry code: (i) −x, −y+2, −z+1.
 

Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under a UGC–BSR one-time Grant to faculty.

References

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 First citationGowda, B. T., Damodara, N. & Jyothi, K. (2005). Int. J. Chem. Kinet. 37, 572–582.  Web of Science CrossRef CAS Google Scholar
 First citationGowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2597.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Usha, K. M. & Jayalakshmi, K. L. (2003). Z. Naturforsch. Teil A, 58, 801–806.  CAS Google Scholar
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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 68| Part 8| August 2012| Page o2307
https://doi.org/10.1107/S160053681202925X
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