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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 7| July 2012| Page o2191
https://doi.org/10.1107/S1600536812027973

3-Acetyl-1-(2,3-di­methyl­phen­yl)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 12 June 2012; accepted 20 June 2012; online 23 June 2012)

In the crystal structure of the title compound, C11H14N2OS, the conformation of the two N—H bonds is anti. The conformation of the C=S and the C=O bonds is also anti. Furthermore, the N—H bond adjacent to the benzene ring is anti to the ortho- and meta-methyl groups. The dihedral angle between the benzene ring and the side chain [N—C(= S)—N—C(=O)—C; maximum deviation = 0.047 (4) Å] is 81.33 (10)°. The NH hydrogen adjacent to the benzene ring and the amide O atom exhibit bifurcated intra- and inter­molecular hydrogen bonding. In the crystal, mol­ecules form inversion dimers, which are linked into chains via R22(12) and R22(8) networks.

Related literature

For studies on 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. (2006[Gowda, B. T., Kožíšek', J. & Fuess, H. (2006). Z. Naturforsch. Teil A, 61, 588-594.]); 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, o2570.]) and of N-chloro­aryl­sulfonamides, see: Jyothi & Gowda (2004[Jyothi, K. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 64-68.]); Shetty & Gowda (2004[Shetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63-72.]).

[Scheme 1]

Experimental

Crystal data

  • C11H14N2OS

  • Mr = 222.30

  • Triclinic, [P \overline 1]

  • a = 5.0552 (7) Å

  • b = 9.869 (2) Å

  • c = 12.028 (3) Å

  • α = 106.71 (1)°

  • β = 91.01 (1)°

  • γ = 94.57 (1)°

  • V = 572.4 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.26 mm−1

  • T = 293 K

  • 0.48 × 0.08 × 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 = 0.886, Tmax = 0.990

  • 3414 measured reflections

  • 2066 independent reflections

  • 1331 reflections with I > 2σ(I)

  • Rint = 0.028
Refinement

  • R[F2 > 2σ(F2)] = 0.065

  • wR(F2) = 0.141

  • S = 1.08

  • 2066 reflections

  • 145 parameters

  • 5 restraints

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

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O1 0.86 (2) 1.97 (3) 2.664 (4) 137 (3)
N1—H1N⋯O1i 0.86 (2) 2.50 (3) 3.168 (4) 136 (3)
N2—H2N⋯S1ii 0.84 (2) 2.54 (2) 3.378 (3) 176 (3)
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+2, -y+1, -z.

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/S1600536812027973/nc2285sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027973/nc2285Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812027973/nc2285Isup3.cml

checkCIF report


Comment top

Thiourea and its derivatives are widely used as precursors or intermediates in synthetic organic chemistry. They are known to exhibit a wide variety of biological activities. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bhat & Gowda, 2000; Gowda et al., 2006; Shahwar et al., 2012); N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-chloroarylsulfonamides (Jyothi & Gowda, 2004; Shetty & Gowda, 2004), in the present work, the crystal structure of 3-acetyl-1-(2,3-dimethylphenyl)thiourea has been determined (Fig. 1).

The conformation of the two N—H bonds are anti to each other, and one of them is anti to the C═S in the urea segment and the other orients away from it. The adjacent N—H bond is anti to the ortho- and meta-methyl groups in the benzene ring. Furthermore, 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).

The side chain is oriented itself with respect to the phenyl ring with the torsion angles of C2—C1—N1—C7 = 83.59 (47)° and C6—C1—N1—C7 = - 99.89 (44)°. The dihedral angle between the phenyl ring and the side chain is 81.33 (10)°.

The hydrogen atom of the NH attached to the phenyl ring and the amide oxygen exhibit a bifurcated hydrogen bonding by showing the simultaneous intra and intermolecular hydrogen bonding. In the crystal, the molecules form inversion type dimers which are linked into infinite chains in terms of R22(12) and R22(8) networks through series of N—H···O and N—H···S intermolecular hydrogen bonds, respectively (Table 1, Fig.2).

Related literature top

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bhat & Gowda (2000); Gowda et al. (2006); Shahwar et al. (2012), of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and of N-chloroarylsulfonamides, see: Jyothi & Gowda (2004); Shetty & Gowda (2004).

Experimental top

3-Acetyl-1-(2,3-dimethylphenyl)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 2,3-dimethylaniline (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.

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

Refinement top

All C—H H atoms were positioned with idealized geometry (methyl H atoms allowed to rotate but not to tip) and were refined isotropic with Uiso(H) = 1.2 Ueq(C) (1.5 for methyl H atoms) using a riding model with C—H = 0.93 Å for aromatic and C—H = 0.96 Å for methyl H atoms. The amino H atoms were refined with the N—H distances restrained to 0.86 (2) Å.

Structure description top

Thiourea and its derivatives are widely used as precursors or intermediates in synthetic organic chemistry. They are known to exhibit a wide variety of biological activities. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bhat & Gowda, 2000; Gowda et al., 2006; Shahwar et al., 2012); N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-chloroarylsulfonamides (Jyothi & Gowda, 2004; Shetty & Gowda, 2004), in the present work, the crystal structure of 3-acetyl-1-(2,3-dimethylphenyl)thiourea has been determined (Fig. 1).

The conformation of the two N—H bonds are anti to each other, and one of them is anti to the C═S in the urea segment and the other orients away from it. The adjacent N—H bond is anti to the ortho- and meta-methyl groups in the benzene ring. Furthermore, 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).

The side chain is oriented itself with respect to the phenyl ring with the torsion angles of C2—C1—N1—C7 = 83.59 (47)° and C6—C1—N1—C7 = - 99.89 (44)°. The dihedral angle between the phenyl ring and the side chain is 81.33 (10)°.

The hydrogen atom of the NH attached to the phenyl ring and the amide oxygen exhibit a bifurcated hydrogen bonding by showing the simultaneous intra and intermolecular hydrogen bonding. In the crystal, the molecules form inversion type dimers which are linked into infinite chains in terms of R22(12) and R22(8) networks through series of N—H···O and N—H···S intermolecular hydrogen bonds, respectively (Table 1, Fig.2).

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bhat & Gowda (2000); Gowda et al. (2006); Shahwar et al. (2012), of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and of N-chloroarylsulfonamides, see: Jyothi & Gowda (2004); 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.
[Figure 2] Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
3-Acetyl-1-(2,3-dimethylphenyl)thiourea top
Crystal data top
C11H14N2OSZ = 2
Mr = 222.30F(000) = 236
Triclinic, P1Dx = 1.290 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.0552 (7) ÅCell parameters from 1147 reflections
b = 9.869 (2) Åθ = 3.5–27.8°
c = 12.028 (3) ŵ = 0.26 mm−1
α = 106.71 (1)°T = 293 K
β = 91.01 (1)°Needle, colourless
γ = 94.57 (1)°0.48 × 0.08 × 0.04 mm
V = 572.4 (2) Å3
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2066 independent reflections
Radiation source: fine-focus sealed tube1331 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Rotation method data acquisition using ω and phi scansθmax = 25.3°, θmin = 3.5°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		h = −6→6
Tmin = 0.886, Tmax = 0.990k = −11→11
3414 measured reflectionsl = −13→14
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0493P)2 + 0.4018P]
where P = (Fo2 + 2Fc2)/3
2066 reflections(Δ/σ)max = 0.003
145 parametersΔρmax = 0.33 e Å−3
5 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C11H14N2OSγ = 94.57 (1)°
Mr = 222.30V = 572.4 (2) Å3
Triclinic, P1Z = 2
a = 5.0552 (7) ÅMo Kα radiation
b = 9.869 (2) ŵ = 0.26 mm−1
c = 12.028 (3) ÅT = 293 K
α = 106.71 (1)°0.48 × 0.08 × 0.04 mm
β = 91.01 (1)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2066 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		1331 reflections with I > 2σ(I)
Tmin = 0.886, Tmax = 0.990Rint = 0.028
3414 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0655 restraints
wR(F2) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.33 e Å−3
2066 reflectionsΔρmin = −0.24 e Å−3
145 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
S11.1098 (2)0.43318 (11)0.14467 (9)0.0458 (3)
O10.4254 (5)0.1213 (3)−0.0465 (2)0.0552 (8)
N10.7872 (6)0.2041 (3)0.1289 (3)0.0432 (8)
H1N0.674 (6)0.140 (3)0.086 (3)0.052*
N20.7252 (6)0.3141 (3)−0.0129 (3)0.0382 (7)
H2N0.773 (7)0.378 (3)−0.043 (3)0.046*
C10.9070 (7)0.1817 (4)0.2310 (3)0.0438 (10)
C20.8249 (7)0.2551 (4)0.3383 (3)0.0477 (10)
C30.9350 (9)0.2228 (5)0.4369 (4)0.0584 (10)
C41.1149 (9)0.1232 (5)0.4189 (4)0.0658 (11)
H41.18710.10230.48310.079*
C51.1947 (10)0.0521 (5)0.3101 (4)0.0717 (12)
H51.3189−0.01430.30200.086*
C61.0896 (8)0.0800 (4)0.2137 (4)0.0538 (11)
H61.13890.03260.13940.065*
C70.8621 (7)0.3091 (4)0.0861 (3)0.0356 (8)
C80.5121 (7)0.2265 (4)−0.0728 (3)0.0384 (9)
C90.3956 (8)0.2699 (4)−0.1700 (3)0.0509 (10)
H9A0.53560.2990−0.21340.076*
H9B0.28950.3476−0.13950.076*
H9C0.28640.1913−0.22010.076*
C100.6334 (8)0.3630 (5)0.3534 (4)0.0613 (12)
H10A0.53920.35130.28080.092*
H10B0.72650.45600.37880.092*
H10C0.50970.35220.41050.092*
C110.8541 (11)0.2953 (6)0.5555 (4)0.0948 (18)
H11A0.67190.26540.56370.142*
H11B0.87340.39620.56800.142*
H11C0.96430.27130.61160.142*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0475 (6)0.0432 (6)0.0496 (6)−0.0111 (4)−0.0123 (4)0.0231 (5)
O10.0659 (18)0.0452 (16)0.0549 (17)−0.0173 (14)−0.0174 (14)0.0224 (14)
N10.050 (2)0.0423 (19)0.0379 (18)−0.0132 (15)−0.0127 (15)0.0177 (15)
N20.0417 (18)0.0414 (19)0.0363 (17)−0.0026 (15)−0.0002 (14)0.0210 (14)
C10.048 (2)0.043 (2)0.044 (2)−0.0116 (19)−0.0029 (18)0.0217 (19)
C20.038 (2)0.051 (3)0.055 (3)−0.0107 (19)0.0014 (19)0.021 (2)
C30.061 (3)0.071 (3)0.045 (2)−0.0172 (17)−0.0050 (19)0.025 (2)
C40.071 (3)0.072 (3)0.064 (2)−0.0141 (18)−0.018 (2)0.041 (2)
C50.079 (3)0.061 (3)0.084 (3)0.009 (2)−0.007 (3)0.035 (2)
C60.057 (3)0.050 (3)0.063 (3)0.001 (2)−0.005 (2)0.030 (2)
C70.040 (2)0.035 (2)0.034 (2)0.0021 (16)0.0001 (16)0.0136 (17)
C80.041 (2)0.038 (2)0.036 (2)0.0006 (18)0.0001 (17)0.0097 (17)
C90.053 (2)0.055 (3)0.047 (2)−0.001 (2)−0.0118 (19)0.020 (2)
C100.060 (3)0.068 (3)0.052 (3)0.002 (2)0.010 (2)0.012 (2)
C110.108 (4)0.120 (5)0.053 (3)−0.017 (4)−0.006 (3)0.029 (3)
Geometric parameters (Å, º) top
S1—C71.671 (4)C4—H40.9300
O1—C81.221 (4)C5—C61.374 (6)
N1—C71.316 (4)C5—H50.9300
N1—C11.440 (4)C6—H60.9300
N1—H1N0.856 (18)C8—C91.484 (5)
N2—C81.375 (4)C9—H9A0.9600
N2—C71.383 (4)C9—H9B0.9600
N2—H2N0.838 (18)C9—H9C0.9600
C1—C21.376 (5)C10—H10A0.9600
C1—C61.391 (5)C10—H10B0.9600
C2—C31.429 (5)C10—H10C0.9600
C2—C101.470 (5)C11—H11A0.9600
C3—C41.366 (6)C11—H11B0.9600
C3—C111.481 (6)C11—H11C0.9600
C4—C51.380 (7)
C7—N1—C1124.6 (3)N1—C7—N2116.9 (3)
C7—N1—H1N115 (3)N1—C7—S1123.6 (3)
C1—N1—H1N120 (3)N2—C7—S1119.5 (3)
C8—N2—C7129.1 (3)O1—C8—N2121.9 (3)
C8—N2—H2N113 (3)O1—C8—C9122.9 (3)
C7—N2—H2N118 (3)N2—C8—C9115.2 (3)
C2—C1—C6124.1 (4)C8—C9—H9A109.5
C2—C1—N1118.7 (4)C8—C9—H9B109.5
C6—C1—N1117.1 (4)H9A—C9—H9B109.5
C1—C2—C3117.0 (4)C8—C9—H9C109.5
C1—C2—C10122.6 (4)H9A—C9—H9C109.5
C3—C2—C10120.4 (4)H9B—C9—H9C109.5
C4—C3—C2118.4 (4)C2—C10—H10A109.5
C4—C3—C11121.1 (4)C2—C10—H10B109.5
C2—C3—C11120.5 (5)H10A—C10—H10B109.5
C3—C4—C5123.1 (4)C2—C10—H10C109.5
C3—C4—H4118.4H10A—C10—H10C109.5
C5—C4—H4118.4H10B—C10—H10C109.5
C6—C5—C4119.7 (5)C3—C11—H11A109.5
C6—C5—H5120.2C3—C11—H11B109.5
C4—C5—H5120.2H11A—C11—H11B109.5
C5—C6—C1117.7 (4)C3—C11—H11C109.5
C5—C6—H6121.2H11A—C11—H11C109.5
C1—C6—H6121.2H11B—C11—H11C109.5
C7—N1—C1—C283.6 (5)C11—C3—C4—C5179.5 (4)
C7—N1—C1—C6−99.9 (4)C3—C4—C5—C6−0.6 (7)
C6—C1—C2—C3−0.4 (5)C4—C5—C6—C10.8 (6)
N1—C1—C2—C3175.8 (3)C2—C1—C6—C5−0.3 (6)
C6—C1—C2—C10179.3 (3)N1—C1—C6—C5−176.6 (4)
N1—C1—C2—C10−4.4 (5)C1—N1—C7—N2179.8 (3)
C1—C2—C3—C40.7 (6)C1—N1—C7—S1−0.1 (5)
C10—C2—C3—C4−179.1 (4)C8—N2—C7—N12.3 (6)
C1—C2—C3—C11−179.0 (4)C8—N2—C7—S1−177.8 (3)
C10—C2—C3—C111.2 (6)C7—N2—C8—O1−5.1 (6)
C2—C3—C4—C5−0.2 (7)C7—N2—C8—C9174.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.86 (2)1.97 (3)2.664 (4)137 (3)
N1—H1N···O1i0.86 (2)2.50 (3)3.168 (4)136 (3)
N2—H2N···S1ii0.84 (2)2.54 (2)3.378 (3)176 (3)
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formulaC11H14N2OS
Mr222.30
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)5.0552 (7), 9.869 (2), 12.028 (3)
α, β, γ (°)106.71 (1), 91.01 (1), 94.57 (1)
V (Å3)572.4 (2)
Z2
Radiation typeMo Kα
µ (mm−1)0.26
Crystal size (mm)0.48 × 0.08 × 0.04
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.886, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections		3414, 2066, 1331
Rint0.028
(sin θ/λ)max (Å−1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.141, 1.08
No. of reflections2066
No. of parameters145
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.33, −0.24

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···O10.856 (18)1.97 (3)2.664 (4)137 (3)
N1—H1N···O1i0.856 (18)2.50 (3)3.168 (4)136 (3)
N2—H2N···S1ii0.838 (18)2.542 (19)3.378 (3)176 (3)
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y+1, −z.
 

Acknowledgements

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

References

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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2191
https://doi.org/10.1107/S1600536812027973
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