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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 o2167
https://doi.org/10.1107/S160053681202747X

2-Formyl-6-meth­­oxy­phenyl cinnamate

N. Manikandan,a S. Murugavel,b* D. Kannanc and M. Bakthadossc‡

aDepartment of Physics, Bharathidasan Engineering College, Nattrampalli, Vellore 635 854, India, bDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, and cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
*Correspondence e-mail: smurugavel27@gmail.com

(Received 15 June 2012; accepted 17 June 2012; online 23 June 2012)

In the title compound, C17H14O4, the C=C bond adopts an E conformation and the dihedral angle between the benzene rings is 73.9 (1)°. The crystal packing features C—H⋯O hydrogen bonds, which generate C(4) chains propagating along the b-axis direction. Weak aromatic π–π stacking inter­actions [centroid–centroid distance = 3.703 (1) Å] are also observed.

Related literature

For the biological properties of cinnamate derivatives, see: Sharma (2011[Sharma, P. (2011). J. Chem. Pharm. Res. 3, 403-423.]). For related structures, see: Kaitner & Stilinović (2007[Kaitner, B. & Stilinović, V. (2007). Acta Cryst. E63, o4347.]); Anuradha et al. (2012[Anuradha, T., Sivakumar, G., Seshadri, P. R. & Bakthadoss, M. (2012). Acta Cryst. E68, o229.]).

[Scheme 1]

Experimental

Crystal data

  • C17H14O4

  • Mr = 282.28

  • Orthorhombic, P b c a

  • a = 10.7908 (7) Å

  • b = 10.4672 (5) Å

  • c = 25.8714 (17) Å

  • V = 2922.2 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.23 × 0.21 × 0.15 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.910, Tmax = 0.941

  • 14344 measured reflections

  • 2665 independent reflections

  • 1909 reflections with I > 2σ(I)

  • Rint = 0.026
Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.106

  • S = 1.01

  • 2665 reflections

  • 192 parameters

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.12 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C9—H9⋯O3i 0.93 2.50 3.415 (2) 168
Symmetry code: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: ORTEP-3 (Farrugia (1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681202747X/hb6858sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681202747X/hb6858Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681202747X/hb6858Isup3.cml

checkCIF report


Comment top

Cinnamic acid and its derivatives including esters and carboxylic functional derivatives are used as important components in flavours, perfumes, synthetic indigo and pharmaceuticals. Cinnamate can act as optical filters or deactivate substrate molecules that have been excited by light for the protection polymers and organic substances. They are used as cosmetic grades and as sunscreen agents to reduce skin damage by blocking UV—A, B (Sharma, 2011). As part of our studies in this area, the crystal structure determination of the title compound was carried out and the results are presented here.

The C9=C10 double bond of the title compound (I) exists in an E-configuration (Fig. 1). The dihedral angle between the two benzene rings is 73.9 (1)°. The geometric parameters of the title molecule agrees well with those reported for similar structures (Kaitner et al., 2007, Anuradha et al., 2012).

The crystal packing features C—H···O hydrogen bonds. Atom C9 at x, y, z donates one proton to atom O3 at 3/2 - x, 1/2 + y, z, forming C(4) chains along the b axis (Fig. 2). The crystal packing (Fig. 3) also features π—π interactions with a Cg—Cgiv seperation of 3.703 (1) Å.[Fig. 3; Cg is the centroid of the C1–C6 benzene ring, symmetry code as in Fig. 3].

Related literature top

For the biological properties of cinnamate derivatives, see: Sharma (2011). For related structures, see: Kaitner & Stilinović (2007); Anuradha et al. (2012).

Experimental top

To a stirred solution of 2-hydroxy-3-methoxybenzaldehyde (1 mmol, 0.154 g) and potassium carbonate (1.5 mmol, 0.207 g) was stirred for 15 minutes in acetonitrile as solvent at room temperature. To this solution, (2E)-3-phenylprop-2-enoylchloride (1 mmol, 0.167 g) was added till the addition is complete. After the completion of the reaction as indicated by TLC, acetonitrile solvent was evaporated. Ethylacetate (15 ml) and water (15 ml) were added to the crude mass. The organic layer was dried over anhydrous sodium sulfate. Removal of solvent led to the crude product. The pure title compound was obtained as a colorless solid (0.250 g, 89% yield). Recrystallization was carried out using ethylacetate as solvent to yield colourless blocks.

Refinement top

H atoms were positioned geometrically, with C–H = 0.93–0.96 Å and constrained to ride on their parent atoms, with Uiso(H) =1.5Ueq for methyl H atoms and 1.2Ueq(C) for other H atoms.

Structure description top

Cinnamic acid and its derivatives including esters and carboxylic functional derivatives are used as important components in flavours, perfumes, synthetic indigo and pharmaceuticals. Cinnamate can act as optical filters or deactivate substrate molecules that have been excited by light for the protection polymers and organic substances. They are used as cosmetic grades and as sunscreen agents to reduce skin damage by blocking UV—A, B (Sharma, 2011). As part of our studies in this area, the crystal structure determination of the title compound was carried out and the results are presented here.

The C9=C10 double bond of the title compound (I) exists in an E-configuration (Fig. 1). The dihedral angle between the two benzene rings is 73.9 (1)°. The geometric parameters of the title molecule agrees well with those reported for similar structures (Kaitner et al., 2007, Anuradha et al., 2012).

The crystal packing features C—H···O hydrogen bonds. Atom C9 at x, y, z donates one proton to atom O3 at 3/2 - x, 1/2 + y, z, forming C(4) chains along the b axis (Fig. 2). The crystal packing (Fig. 3) also features π—π interactions with a Cg—Cgiv seperation of 3.703 (1) Å.[Fig. 3; Cg is the centroid of the C1–C6 benzene ring, symmetry code as in Fig. 3].

For the biological properties of cinnamate derivatives, see: Sharma (2011). For related structures, see: Kaitner & Stilinović (2007); Anuradha et al. (2012).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia (1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing displacement ellipsoids at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure of (I) showing intermolecular C—H···O hydrogen bonds (dotted lines), forming C(4) chains along the b axis. For clarity H atoms involved in the hydrogen bonds are shown. [Symmetry codes:(i)3/2 - x, 1/2 + y, z; (ii)x, 1 + y, z; (iii)3/2 - x, 3/2 + y, z].
[Figure 3] Fig. 3. A view of the π—π interactions (dotted lines) in the crystal structure of the title compound. Cg denotes centroid of the C1–C6 benzene ring. [Symmetry code: (iv)1 - x, -y, 1 - z].
2-Formyl-6-methoxyphenyl cinnamate top
Crystal data top
C17H14O4F(000) = 1184
Mr = 282.28Dx = 1.283 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2879 reflections
a = 10.7908 (7) Åθ = 1.0–1.0°
b = 10.4672 (5) ŵ = 0.09 mm−1
c = 25.8714 (17) ÅT = 293 K
V = 2922.2 (3) Å3Block, colourless
Z = 80.23 × 0.21 × 0.15 mm
Data collection top
Bruker APEXII CCD
diffractometer		2665 independent reflections
Radiation source: fine-focus sealed tube1909 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 10.0 pixels mm-1θmax = 26.0°, θmin = 2.5°
ω scansh = −13→13
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −9→11
Tmin = 0.910, Tmax = 0.941l = −31→31
14344 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.106 w = 1/[σ2(Fo2) + (0.0446P)2 + 0.7231P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
2665 reflectionsΔρmax = 0.15 e Å−3
192 parametersΔρmin = −0.12 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0020 (5)
Crystal data top
C17H14O4V = 2922.2 (3) Å3
Mr = 282.28Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 10.7908 (7) ŵ = 0.09 mm−1
b = 10.4672 (5) ÅT = 293 K
c = 25.8714 (17) Å0.23 × 0.21 × 0.15 mm
Data collection top
Bruker APEXII CCD
diffractometer		2665 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1909 reflections with I > 2σ(I)
Tmin = 0.910, Tmax = 0.941Rint = 0.026
14344 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 1.01Δρmax = 0.15 e Å−3
2665 reflectionsΔρmin = −0.12 e Å−3
192 parameters
Special details top

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
C10.62871 (15)−0.06915 (15)0.54858 (6)0.0487 (4)
C20.54050 (16)−0.15242 (16)0.56771 (7)0.0552 (4)
C30.48566 (18)−0.23727 (18)0.53357 (8)0.0686 (5)
H30.4252−0.29350.54530.082*
C40.5205 (2)−0.2388 (2)0.48191 (8)0.0732 (6)
H40.4827−0.29590.45930.088*
C50.60927 (19)−0.15776 (18)0.46393 (7)0.0649 (5)
H50.6326−0.16030.42930.078*
C60.66465 (16)−0.07149 (16)0.49726 (7)0.0532 (4)
C70.7586 (2)0.0175 (2)0.47767 (8)0.0702 (5)
H70.78650.08130.49980.084*
C80.76334 (15)−0.01222 (16)0.61648 (6)0.0459 (4)
C90.78497 (15)0.08922 (16)0.65399 (6)0.0491 (4)
H90.75210.17000.64800.059*
C100.85036 (15)0.06857 (17)0.69633 (6)0.0509 (4)
H100.8863−0.01190.69930.061*
C110.87318 (14)0.15626 (16)0.73902 (6)0.0484 (4)
C120.82650 (17)0.28000 (17)0.73974 (6)0.0595 (5)
H120.78120.31010.71170.071*
C130.84677 (18)0.35820 (19)0.78160 (7)0.0663 (5)
H130.81490.44070.78160.080*
C140.91335 (17)0.3161 (2)0.82338 (7)0.0667 (5)
H140.92580.36940.85170.080*
C150.96137 (18)0.1953 (2)0.82313 (7)0.0703 (6)
H151.00740.16650.85120.084*
C160.94166 (17)0.11608 (19)0.78136 (6)0.0619 (5)
H160.97490.03410.78160.074*
C170.41618 (19)−0.2177 (2)0.63873 (9)0.0923 (7)
H17A0.3401−0.19470.62190.138*
H17B0.4085−0.20320.67520.138*
H17C0.4336−0.30630.63250.138*
O10.80202 (17)0.01350 (16)0.43495 (6)0.0987 (5)
O20.67581 (11)0.02494 (10)0.58150 (4)0.0542 (3)
O30.81108 (12)−0.11529 (12)0.61497 (5)0.0630 (4)
O40.51428 (13)−0.14196 (13)0.61881 (5)0.0731 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0519 (10)0.0386 (10)0.0557 (9)0.0070 (7)−0.0156 (8)−0.0053 (7)
C20.0530 (10)0.0508 (11)0.0617 (10)0.0072 (8)−0.0079 (8)−0.0057 (8)
C30.0582 (11)0.0561 (12)0.0914 (15)−0.0041 (9)−0.0122 (10)−0.0078 (10)
C40.0754 (13)0.0635 (14)0.0806 (14)0.0058 (11)−0.0266 (11)−0.0246 (11)
C50.0766 (13)0.0622 (13)0.0560 (10)0.0125 (11)−0.0150 (10)−0.0123 (9)
C60.0599 (11)0.0471 (11)0.0527 (9)0.0099 (8)−0.0109 (8)−0.0010 (8)
C70.0815 (14)0.0650 (14)0.0641 (11)0.0035 (11)−0.0039 (11)0.0060 (10)
C80.0482 (9)0.0427 (11)0.0468 (8)−0.0014 (8)−0.0038 (7)0.0034 (7)
C90.0550 (10)0.0404 (10)0.0520 (9)−0.0011 (8)−0.0064 (8)−0.0009 (7)
C100.0528 (10)0.0467 (11)0.0531 (9)0.0010 (8)−0.0034 (8)0.0018 (7)
C110.0483 (9)0.0520 (11)0.0449 (8)−0.0040 (8)−0.0014 (7)0.0005 (7)
C120.0710 (12)0.0564 (12)0.0510 (10)−0.0017 (9)−0.0106 (9)−0.0022 (8)
C130.0793 (13)0.0588 (12)0.0607 (11)−0.0032 (10)−0.0011 (10)−0.0107 (9)
C140.0587 (11)0.0911 (16)0.0502 (10)−0.0126 (11)0.0015 (9)−0.0172 (10)
C150.0601 (11)0.1040 (17)0.0469 (9)0.0032 (11)−0.0090 (8)−0.0033 (10)
C160.0625 (11)0.0700 (13)0.0532 (10)0.0090 (9)−0.0073 (9)0.0018 (9)
C170.0650 (13)0.118 (2)0.0936 (16)−0.0043 (13)0.0096 (12)0.0217 (14)
O10.1247 (14)0.0973 (12)0.0741 (10)−0.0031 (10)0.0230 (9)0.0072 (8)
O20.0664 (7)0.0407 (7)0.0556 (6)0.0052 (5)−0.0191 (6)−0.0055 (5)
O30.0680 (8)0.0495 (8)0.0717 (8)0.0140 (6)−0.0187 (6)−0.0094 (6)
O40.0713 (9)0.0803 (10)0.0678 (8)−0.0064 (7)0.0058 (7)−0.0038 (7)
Geometric parameters (Å, º) top
C1—C21.382 (2)C9—H90.9300
C1—C61.383 (2)C10—C111.457 (2)
C1—O21.3978 (19)C10—H100.9300
C2—O41.356 (2)C11—C161.387 (2)
C2—C31.385 (2)C11—C121.390 (2)
C3—C41.389 (3)C12—C131.375 (2)
C3—H30.9300C12—H120.9300
C4—C51.361 (3)C13—C141.371 (3)
C4—H40.9300C13—H130.9300
C5—C61.384 (2)C14—C151.366 (3)
C5—H50.9300C14—H140.9300
C6—C71.468 (3)C15—C161.379 (3)
C7—O11.201 (2)C15—H150.9300
C7—H70.9300C16—H160.9300
C8—O31.1961 (19)C17—O41.419 (2)
C8—O21.3646 (18)C17—H17A0.9600
C8—C91.457 (2)C17—H17B0.9600
C9—C101.321 (2)C17—H17C0.9600
C2—C1—C6121.71 (15)C9—C10—H10116.0
C2—C1—O2118.45 (15)C11—C10—H10116.0
C6—C1—O2119.70 (15)C16—C11—C12117.72 (15)
O4—C2—C1116.23 (15)C16—C11—C10119.85 (16)
O4—C2—C3125.74 (18)C12—C11—C10122.41 (15)
C1—C2—C3118.03 (17)C13—C12—C11120.51 (17)
C2—C3—C4120.37 (19)C13—C12—H12119.7
C2—C3—H3119.8C11—C12—H12119.7
C4—C3—H3119.8C14—C13—C12120.87 (19)
C5—C4—C3120.80 (18)C14—C13—H13119.6
C5—C4—H4119.6C12—C13—H13119.6
C3—C4—H4119.6C15—C14—C13119.51 (18)
C4—C5—C6119.83 (18)C15—C14—H14120.2
C4—C5—H5120.1C13—C14—H14120.2
C6—C5—H5120.1C14—C15—C16120.12 (18)
C1—C6—C5119.24 (18)C14—C15—H15119.9
C1—C6—C7120.93 (16)C16—C15—H15119.9
C5—C6—C7119.82 (17)C15—C16—C11121.26 (18)
O1—C7—C6124.4 (2)C15—C16—H16119.4
O1—C7—H7117.8C11—C16—H16119.4
C6—C7—H7117.8O4—C17—H17A109.5
O3—C8—O2122.24 (14)O4—C17—H17B109.5
O3—C8—C9127.58 (15)H17A—C17—H17B109.5
O2—C8—C9110.17 (14)O4—C17—H17C109.5
C10—C9—C8121.24 (16)H17A—C17—H17C109.5
C10—C9—H9119.4H17B—C17—H17C109.5
C8—C9—H9119.4C8—O2—C1117.06 (12)
C9—C10—C11128.01 (16)C2—O4—C17117.68 (16)
C6—C1—C2—O4179.15 (15)C8—C9—C10—C11−175.41 (15)
O2—C1—C2—O4−5.3 (2)C9—C10—C11—C16178.04 (17)
C6—C1—C2—C3−1.7 (2)C9—C10—C11—C12−0.6 (3)
O2—C1—C2—C3173.89 (14)C16—C11—C12—C13−0.9 (3)
O4—C2—C3—C4179.98 (17)C10—C11—C12—C13177.80 (17)
C1—C2—C3—C40.9 (3)C11—C12—C13—C140.1 (3)
C2—C3—C4—C50.3 (3)C12—C13—C14—C150.8 (3)
C3—C4—C5—C6−0.8 (3)C13—C14—C15—C16−0.7 (3)
C2—C1—C6—C51.2 (2)C14—C15—C16—C11−0.1 (3)
O2—C1—C6—C5−174.30 (14)C12—C11—C16—C150.9 (3)
C2—C1—C6—C7−179.88 (16)C10—C11—C16—C15−177.80 (17)
O2—C1—C6—C74.6 (2)O3—C8—O2—C110.1 (2)
C4—C5—C6—C10.0 (3)C9—C8—O2—C1−169.00 (14)
C4—C5—C6—C7−178.85 (17)C2—C1—O2—C878.41 (18)
C1—C6—C7—O1173.14 (19)C6—C1—O2—C8−105.90 (17)
C5—C6—C7—O1−8.0 (3)C1—C2—O4—C17174.31 (16)
O3—C8—C9—C10−10.2 (3)C3—C2—O4—C17−4.8 (3)
O2—C8—C9—C10168.89 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···O3i0.932.503.415 (2)168
Symmetry code: (i) −x+3/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC17H14O4
Mr282.28
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)293
a, b, c (Å)10.7908 (7), 10.4672 (5), 25.8714 (17)
V (Å3)2922.2 (3)
Z8
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.23 × 0.21 × 0.15
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.910, 0.941
No. of measured, independent and
observed [I > 2σ(I)] reflections		14344, 2665, 1909
Rint0.026
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.106, 1.01
No. of reflections2665
No. of parameters192
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.15, −0.12

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia (1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···O3i0.932.503.415 (2)168
Symmetry code: (i) −x+3/2, y+1/2, z.
 

Footnotes

‡Additional correspondence author, e-mail: bhakthadoss@yahoo.com.

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

First citationAnuradha, T., Sivakumar, G., Seshadri, P. R. & Bakthadoss, M. (2012). Acta Cryst. E68, o229.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2167
https://doi.org/10.1107/S160053681202747X
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