Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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 o2306
https://doi.org/10.1107/S1600536812029248

3-Acetyl-1-(2,6-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 27 June 2012; online 4 July 2012)

In the title compound, C11H14N2OS, the two N—H bonds are anti to each other and one of them is anti to the C=S and the other is syn. Further, the amide C=S and the C=O groups are anti to each other. The dihedral angle between the benzene ring and the side chain is 83.74 (5)°. An intra­molecular N—H⋯O hydrogen bond occurs. In the crystal, mol­ecules are linked into inversion dimers by pairs of N—H⋯S inter­actions.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: 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: 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

  • C11H14N2OS

  • Mr = 222.31

  • Triclinic, [P \overline 1]

  • a = 8.008 (1) Å

  • b = 8.211 (1) Å

  • c = 10.037 (1) Å

  • α = 89.39 (1)°

  • β = 77.65 (1)°

  • γ = 64.71 (1)°

  • V = 580.47 (13) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.26 mm−1

  • T = 295 K

  • 0.30 × 0.20 × 0.08 mm
Data collection

  • Oxford Diffraction Xcalibur Sapphire CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton,England.]) Tmin = 0.928, Tmax = 0.980

  • 3904 measured reflections

  • 2362 independent reflections

  • 1858 reflections with I > 2σ(I)

  • Rint = 0.012
Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.115

  • S = 1.06

  • 2362 reflections

  • 145 parameters

  • 2 restraints

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

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.31 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) 1.97 (2) 2.658 (2) 138 (2)
N2—H2N⋯S1i 0.85 (2) 2.58 (2) 3.4012 (16) 164 (2)
Symmetry code: (i) -x, -y+1, -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/S1600536812029248/rk2369sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812029248/rk2369Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812029248/rk2369Isup3.cml

checkCIF report


Comment top

Thiourea and its derivatives are widely used as precursors or intermediates in synthetic organic chemistry. They 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 (Gowda et al., 2006; 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-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 and the other is syn in the urea moiety. 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 = 94.77 (22)° and C6-C1-N1-C7 = -87.11 (23)°. The dihedral angle between the phenyl ring and the side chain is 83.74 (5)°.

The structure shows intramolecular hydrogen bonding between the hydrogen atom of the NH attached to the phenyl ring and the amide oxygen. In the crystal, the molecules form inversion type dimers through N–H···S intermolecular classical hydrogen bonds (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: Gowda et al. (2006); Shahwar et al. (2012), ofN-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and of N-chloroarylsulfonamides, see: Gowda et al. (2005); Shetty & Gowda (2004).

Experimental top

The 3-acetyl-1-(2,6-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 2,6-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 IR spectrum. The characteristic absorptions observed are 3156.1 cm-1, 1698.1 cm-1, 1365.7 cm-1 and 710.4 cm-1 for the stretching bands of -N–H, -C═O, -C–N- and -C═S, respectively.

Prism like light 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

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

Structure description top

Thiourea and its derivatives are widely used as precursors or intermediates in synthetic organic chemistry. They 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 (Gowda et al., 2006; 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-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 and the other is syn in the urea moiety. 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 = 94.77 (22)° and C6-C1-N1-C7 = -87.11 (23)°. The dihedral angle between the phenyl ring and the side chain is 83.74 (5)°.

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

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2006); Shahwar et al. (2012), ofN-(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. Displacement ellipsoids are drawn at the 50% probability level. H atom are presented as a small spheres of arbitrary radius.
[Figure 2] Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
3-Acetyl-1-(2,6-dimethylphenyl)thiourea top
Crystal data top
C11H14N2OSZ = 2
Mr = 222.31F(000) = 236
Triclinic, P1Dx = 1.272 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.008 (1) ÅCell parameters from 1747 reflections
b = 8.211 (1) Åθ = 2.8–27.6°
c = 10.037 (1) ŵ = 0.26 mm−1
α = 89.39 (1)°T = 295 K
β = 77.65 (1)°Prism, light yellow
γ = 64.71 (1)°0.30 × 0.20 × 0.08 mm
V = 580.47 (13) Å3
Data collection top
Oxford Diffraction Xcalibur Sapphire CCD
diffractometer		2362 independent reflections
Radiation source: fine-focus sealed tube1858 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.012
Rotation method data acquisition using ω and φ scansθmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		h = −9→6
Tmin = 0.928, Tmax = 0.980k = −10→10
3904 measured reflectionsl = −12→9
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0515P)2 + 0.2097P]
where P = (Fo2 + 2Fc2)/3
2362 reflections(Δ/σ)max = 0.016
145 parametersΔρmax = 0.21 e Å−3
2 restraintsΔρmin = −0.31 e Å−3
Crystal data top
C11H14N2OSγ = 64.71 (1)°
Mr = 222.31V = 580.47 (13) Å3
Triclinic, P1Z = 2
a = 8.008 (1) ÅMo Kα radiation
b = 8.211 (1) ŵ = 0.26 mm−1
c = 10.037 (1) ÅT = 295 K
α = 89.39 (1)°0.30 × 0.20 × 0.08 mm
β = 77.65 (1)°
Data collection top
Oxford Diffraction Xcalibur Sapphire CCD
diffractometer		2362 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		1858 reflections with I > 2σ(I)
Tmin = 0.928, Tmax = 0.980Rint = 0.012
3904 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0412 restraints
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.21 e Å−3
2362 reflectionsΔρmin = −0.31 e Å−3
145 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C10.0904 (2)0.0786 (2)0.13742 (17)0.0388 (4)
C20.1028 (3)−0.0846 (3)0.1866 (2)0.0467 (5)
C30.2402 (3)−0.2433 (3)0.1110 (2)0.0583 (6)
H30.2520−0.35420.14150.070*
C40.3592 (3)−0.2388 (3)−0.0087 (2)0.0605 (6)
H40.4507−0.3463−0.05840.073*
C50.3434 (3)−0.0761 (3)−0.0552 (2)0.0553 (6)
H50.4246−0.0751−0.13640.066*
C60.2081 (3)0.0875 (3)0.01660 (19)0.0441 (4)
C7−0.0262 (2)0.3365 (2)0.30688 (17)0.0401 (4)
C8−0.3639 (3)0.5655 (3)0.35392 (19)0.0476 (5)
C9−0.4949 (3)0.7457 (3)0.4319 (3)0.0671 (7)
H9A−0.43250.82370.42120.080*
H9B−0.52850.72970.52720.080*
H9C−0.60770.79890.39720.080*
C10−0.0265 (4)−0.0907 (4)0.3167 (3)0.0736 (7)
H10A−0.1540−0.04370.30480.088*
H10B−0.0218−0.01890.38940.088*
H10C0.0136−0.21350.33930.088*
C110.1920 (3)0.2635 (3)−0.0344 (2)0.0621 (6)
H11A0.19010.33960.03850.075*
H11B0.07680.3217−0.06560.075*
H11C0.29870.2425−0.10870.075*
N1−0.0546 (2)0.2439 (2)0.21360 (16)0.0434 (4)
H1N−0.166 (2)0.286 (3)0.203 (2)0.052*
N2−0.1819 (2)0.4932 (2)0.37213 (16)0.0446 (4)
H2N−0.158 (3)0.546 (3)0.4329 (19)0.054*
O1−0.4147 (2)0.4896 (2)0.27946 (18)0.0697 (5)
S10.18238 (7)0.27758 (8)0.34744 (6)0.0605 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0349 (9)0.0356 (9)0.0395 (9)−0.0070 (7)−0.0135 (7)−0.0102 (7)
C20.0511 (11)0.0436 (11)0.0458 (10)−0.0171 (9)−0.0189 (8)−0.0028 (8)
C30.0619 (13)0.0365 (11)0.0731 (14)−0.0107 (10)−0.0315 (12)−0.0045 (10)
C40.0471 (11)0.0438 (12)0.0716 (15)0.0030 (9)−0.0233 (11)−0.0238 (10)
C50.0383 (10)0.0656 (14)0.0449 (11)−0.0080 (9)−0.0061 (8)−0.0163 (10)
C60.0399 (9)0.0452 (10)0.0420 (10)−0.0120 (8)−0.0129 (8)−0.0060 (8)
C70.0387 (9)0.0384 (9)0.0366 (9)−0.0122 (8)−0.0048 (7)−0.0075 (7)
C80.0425 (10)0.0437 (11)0.0444 (10)−0.0086 (8)−0.0068 (8)−0.0076 (8)
C90.0521 (12)0.0519 (13)0.0708 (15)0.0008 (10)−0.0109 (11)−0.0173 (11)
C100.0924 (19)0.0756 (17)0.0596 (14)−0.0442 (15)−0.0147 (13)0.0097 (12)
C110.0633 (14)0.0621 (14)0.0605 (13)−0.0273 (11)−0.0133 (11)0.0067 (11)
N10.0352 (8)0.0397 (9)0.0463 (9)−0.0069 (7)−0.0106 (7)−0.0145 (7)
N20.0404 (8)0.0405 (8)0.0437 (9)−0.0100 (7)−0.0068 (7)−0.0148 (7)
O10.0475 (8)0.0647 (10)0.0810 (11)−0.0048 (7)−0.0238 (8)−0.0261 (8)
S10.0389 (3)0.0689 (4)0.0590 (3)−0.0087 (2)−0.0118 (2)−0.0315 (3)
Geometric parameters (Å, º) top
C1—C61.390 (3)C8—O11.212 (2)
C1—C21.394 (3)C8—N21.372 (3)
C1—N11.439 (2)C8—C91.500 (3)
C2—C31.387 (3)C9—H9A0.9600
C2—C101.498 (3)C9—H9B0.9600
C3—C41.376 (3)C9—H9C0.9600
C3—H30.9300C10—H10A0.9600
C4—C51.373 (3)C10—H10B0.9600
C4—H40.9300C10—H10C0.9600
C5—C61.393 (3)C11—H11A0.9600
C5—H50.9300C11—H11B0.9600
C6—C111.490 (3)C11—H11C0.9600
C7—N11.327 (2)N1—H1N0.839 (15)
C7—N21.392 (2)N2—H2N0.848 (15)
C7—S11.6694 (19)
C6—C1—C2122.75 (16)C8—C9—H9A109.5
C6—C1—N1119.14 (17)C8—C9—H9B109.5
C2—C1—N1118.08 (16)H9A—C9—H9B109.5
C3—C2—C1117.73 (19)C8—C9—H9C109.5
C3—C2—C10120.5 (2)H9A—C9—H9C109.5
C1—C2—C10121.76 (18)H9B—C9—H9C109.5
C4—C3—C2120.8 (2)C2—C10—H10A109.5
C4—C3—H3119.6C2—C10—H10B109.5
C2—C3—H3119.6H10A—C10—H10B109.5
C5—C4—C3120.25 (18)C2—C10—H10C109.5
C5—C4—H4119.9H10A—C10—H10C109.5
C3—C4—H4119.9H10B—C10—H10C109.5
C4—C5—C6121.4 (2)C6—C11—H11A109.5
C4—C5—H5119.3C6—C11—H11B109.5
C6—C5—H5119.3H11A—C11—H11B109.5
C1—C6—C5117.06 (19)C6—C11—H11C109.5
C1—C6—C11121.87 (17)H11A—C11—H11C109.5
C5—C6—C11121.07 (19)H11B—C11—H11C109.5
N1—C7—N2116.66 (16)C7—N1—C1123.82 (15)
N1—C7—S1124.10 (13)C7—N1—H1N115.6 (15)
N2—C7—S1119.24 (13)C1—N1—H1N120.5 (15)
O1—C8—N2122.32 (17)C8—N2—C7128.57 (16)
O1—C8—C9122.46 (19)C8—N2—H2N118.1 (15)
N2—C8—C9115.22 (18)C7—N2—H2N113.3 (15)
C6—C1—C2—C30.5 (3)N1—C1—C6—C111.8 (3)
N1—C1—C2—C3178.56 (16)C4—C5—C6—C10.2 (3)
C6—C1—C2—C10−179.58 (19)C4—C5—C6—C11179.9 (2)
N1—C1—C2—C10−1.5 (3)N2—C7—N1—C1−179.56 (17)
C1—C2—C3—C4−0.2 (3)S1—C7—N1—C11.3 (3)
C10—C2—C3—C4179.9 (2)C6—C1—N1—C7−87.1 (2)
C2—C3—C4—C5−0.1 (3)C2—C1—N1—C794.8 (2)
C3—C4—C5—C60.1 (3)O1—C8—N2—C74.7 (3)
C2—C1—C6—C5−0.5 (3)C9—C8—N2—C7−174.9 (2)
N1—C1—C6—C5−178.51 (15)N1—C7—N2—C80.6 (3)
C2—C1—C6—C11179.82 (18)S1—C7—N2—C8179.79 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.84 (2)1.97 (2)2.658 (2)138 (2)
N2—H2N···S1i0.85 (2)2.58 (2)3.4012 (16)164 (2)
Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC11H14N2OS
Mr222.31
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)8.008 (1), 8.211 (1), 10.037 (1)
α, β, γ (°)89.39 (1), 77.65 (1), 64.71 (1)
V (Å3)580.47 (13)
Z2
Radiation typeMo Kα
µ (mm−1)0.26
Crystal size (mm)0.30 × 0.20 × 0.08
Data collection
DiffractometerOxford Diffraction Xcalibur Sapphire CCD
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.928, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections		3904, 2362, 1858
Rint0.012
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.115, 1.06
No. of reflections2362
No. of parameters145
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.21, −0.31

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···O10.839 (15)1.972 (18)2.658 (2)138 (2)
N2—H2N···S1i0.848 (15)2.579 (16)3.4012 (16)163.7 (19)
Symmetry code: (i) −x, −y+1, −z+1.
 

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

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, o2570.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Kožíšek, J. & Fuess, H. (2006). Z. Naturforsch. Teil A, 61, 588–594.  CAS Google Scholar
 First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton,England.  Google Scholar
 First citationShahwar, D., Tahir, M. N., Chohan, M. M., Ahmad, N. & Raza, M. A. (2012). Acta Cryst. E68, o1160.  CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationShetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63–72.  CAS Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 8| August 2012| Page o2306
https://doi.org/10.1107/S1600536812029248
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS