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 67| Part 8| August 2011| Page o1934
doi:10.1107/S1600536811026122

2-[(E)-(2,4,6-Tri­chloro­phen­yl)imino­meth­yl]phenol

Hoong-Kun Fun,a*‡ Ching Kheng Quah,a§ S. Viveka,b D. J. Madhukumarb and G. K. Nagarajab

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Chemistry, Mangalore University, Karnataka, India
*Correspondence e-mail: hkfun@usm.my

(Received 28 June 2011; accepted 1 July 2011; online 6 July 2011)

The title mol­ecule, C13H8Cl3NO, exists in a trans configuration with respect to the C=N bond [1.278 (2) Å]. The benzene rings form a dihedral angle of 24.64 (11)°. The mol­ecular structure is stabilized by an intra­molecular O—H⋯N hydrogen bond, which generates an S(6) ring motif. In the crystal, π–π stacking inter­actions [centroid–centroid distances = 3.6893 (14) Å] are observed.

Related literature

For general background to and the pharmacological activity of Schiff base compounds, see: Shapiro (1998[Shapiro, H. K. (1998). Am. J. Ther. 5, 323-353.]); Villar et al. (2004[Villar, R., Encio, I., Migliaccio, M., Gil, M. G. & Martinez-Merino, V. (2004). Bioorg. Med. Chem. 12, 963-968.]); Venugopal & Jayashree (2008[Venugopal, K. N. & Jayashree, B. S. (2008). Indian J. Pharm. Sci. 70, 88-91.]); Pandey et al. (2003[Pandey, S. N., Lakshmi, V. S. & Pandey, A. (2003). Indian J. Pharm. Sci. 65, 213-222.]); Bhat et al. (2005[Bhat, M. A., Imran, M., Khan, S. A. & Siddiqui, N. (2005). J. Pharm. Sci. 67, 151-159.]); Wadher et al. (2009[Wadher, S. J., Puranik, M. P., Karande, N. A. & Yeole, P. G. (2009). Int. J. PharmTech Res. 1, 22-33.]). For related structures, see: Fun et al. (2011a[Fun, H.-K., Quah, C. K., Viveka, S., Madhukumar, D. J. & Prasad, D. J. (2011b). Acta Cryst. E67, o1932.],b[Fun, H.-K., Quah, C. K., Viveka, S., Madhukumar, D. J. & Nagaraja, G. K. (2011a). Acta Cryst. E67, o1933.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C13H8Cl3NO

  • Mr = 300.55

  • Monoclinic, P 21 /c

  • a = 12.8847 (16) Å

  • b = 6.9505 (9) Å

  • c = 14.4265 (18) Å

  • β = 96.612 (2)°

  • V = 1283.4 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.70 mm−1

  • T = 296 K

  • 0.36 × 0.19 × 0.14 mm
Data collection

  • Bruker SMART APEXII DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.785, Tmax = 0.908

  • 10136 measured reflections

  • 3782 independent reflections

  • 2586 reflections with I > 2σ(I)

  • Rint = 0.027
Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.124

  • S = 1.02

  • 3782 reflections

  • 167 parameters

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

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.44 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1O1⋯N1 0.79 (3) 1.94 (3) 2.633 (2) 146 (3)

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811026122/lh5276sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026122/lh5276Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026122/lh5276Isup3.cml

checkCIF report


Comment top

Schiff bases are the important compound owing to their wide range of biological activities and industrial application. The synthesis and structural research of Schiff bases are derived from aldehydes and amines bearing various alkyl and aryl N-substituents. Schiff base ligands may contain a variety of substituents with different electron-donating or electron-withdrawing groups and therefore may have interesting chemical properties. They have attracted particular interest due to their biological activities (Shapiro, 1998). They have been found to posses the pharmacological activities such as antimalarial, anticancer (Villar et al., 2004) antibacterial (Venugopal & Jayashree, 2008) antifungal (Pandey et al., 2003) antitubercular (Bhat et al., 2005), anti-inflammatory and antimicrobial (Wadher et al., 2009) properties.

In the title molecule (Fig. 1), the benzene rings (C1-C6 and C8-C13) form a dihedral angle of 24.64 (11)°. The title molecule exists in trans configuration with respect to the C7═N1 bond [C7═N1 = 1.278 (2) Å]. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun et al., 2011a,b). The molecular structure is stabilized by an intramolecular O1–H1O1···N1 hydrogen bond (Table 1) which generates a S(6) ring motif (Fig. 1, Bernstein et al., 1995).

In the crystal packing, π-π stacking interactions between the centroid of C1-C6 (Cg1) and C8-C13 (Cg2) benzene rings, with Cg1···Cg2i distance of 3.6893 (14) Å [symmetry code: (i) -x, -1/2+y, 3/2-z] are observed. No significant intermolecular hydrogen bonds are observed.

Related literature top

For general background to and the pharmacological activity of Schiff base compounds, see: Shapiro (1998); Villar et al. (2004); Venugopal & Jayashree (2008); Pandey et al. (2003); Bhat et al. (2005); Wadher et al. (2009). For related structures, see: Fun et al. (2011a,b). For hydrogen-bond motifs, see: Bernstein et al. (1995). For standard bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of salicylaldehyde (0.01 mol) and 2,4,6-trichloroaniline (0.01 mol) was dissolved in a minimum amount of ethanol, followed by addition of 2 mL glacial acetic acid. The mixture was refluxed gently for 4-5 h. The reaction was monitored by TLC. After completion of the reaction, the mixture was poured into a beaker containing crushed ice. The precipitate obtained was filtered, dried and recrystallized from ethanol. Yield: 68%, m.p. 425-426 K.

Refinement top

H1O1 atom was located in a difference Fourier map and refined freely [O1–H1O1 = 0.79 (3) Å]. The remaining H atoms were positioned geometrically and refined using a riding model with C–H = 0.93 Å and Uiso(H) = 1.2 Ueq(C). The highest residual electron density peak and the deepest hole are located at 0.93 and 0.85 Å from Cl3, respectively.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms. An intramolecular hydrogen bond is shown as a dashed line.
2-[(E)-(2,4,6-Trichlorophenyl)iminomethyl]phenol top
Crystal data top
C13H8Cl3NOF(000) = 608
Mr = 300.55Dx = 1.556 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3223 reflections
a = 12.8847 (16) Åθ = 2.9–30.0°
b = 6.9505 (9) ŵ = 0.70 mm−1
c = 14.4265 (18) ÅT = 296 K
β = 96.612 (2)°Block, yellow
V = 1283.4 (3) Å30.36 × 0.19 × 0.14 mm
Z = 4
Data collection top
Bruker SMART APEXII DUO CCD area-detector
diffractometer		3782 independent reflections
Radiation source: fine-focus sealed tube2586 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ϕ and ω scansθmax = 30.2°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −18→18
Tmin = 0.785, Tmax = 0.908k = −9→9
10136 measured reflectionsl = −20→20
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0489P)2 + 0.6136P]
where P = (Fo2 + 2Fc2)/3
3782 reflections(Δ/σ)max < 0.001
167 parametersΔρmax = 0.45 e Å−3
0 restraintsΔρmin = −0.44 e Å−3
Crystal data top
C13H8Cl3NOV = 1283.4 (3) Å3
Mr = 300.55Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.8847 (16) ŵ = 0.70 mm−1
b = 6.9505 (9) ÅT = 296 K
c = 14.4265 (18) Å0.36 × 0.19 × 0.14 mm
β = 96.612 (2)°
Data collection top
Bruker SMART APEXII DUO CCD area-detector
diffractometer		3782 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2586 reflections with I > 2σ(I)
Tmin = 0.785, Tmax = 0.908Rint = 0.027
10136 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.45 e Å−3
3782 reflectionsΔρmin = −0.44 e Å−3
167 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl10.05175 (4)0.34050 (9)0.92951 (3)0.05264 (16)
Cl20.44455 (4)0.27949 (11)0.84597 (5)0.0669 (2)
Cl30.35845 (4)0.16620 (13)0.63858 (4)0.0723 (2)
O1−0.20343 (13)0.2343 (3)0.77771 (11)0.0562 (4)
N1−0.01212 (11)0.2621 (2)0.73161 (11)0.0370 (3)
C10.13702 (14)0.3001 (3)0.84736 (13)0.0368 (4)
C20.24358 (14)0.3061 (3)0.87539 (14)0.0427 (4)
H2A0.26850.33440.93690.051*
C30.31237 (14)0.2693 (3)0.81056 (15)0.0428 (4)
C40.27450 (14)0.2244 (3)0.71929 (14)0.0427 (4)
C50.16785 (14)0.2223 (3)0.69162 (13)0.0408 (4)
H5A0.14320.19310.63010.049*
C60.09726 (13)0.2636 (3)0.75513 (12)0.0346 (4)
C7−0.05235 (13)0.3079 (3)0.64944 (13)0.0372 (4)
H7A−0.00840.34370.60560.045*
C8−0.16440 (14)0.3060 (3)0.62241 (14)0.0387 (4)
C9−0.20251 (16)0.3408 (4)0.52901 (15)0.0514 (5)
H9A−0.15580.36400.48570.062*
C10−0.30845 (17)0.3411 (4)0.50043 (18)0.0628 (7)
H10A−0.33330.36230.43820.075*
C11−0.37712 (17)0.3093 (4)0.56579 (19)0.0638 (7)
H11A−0.44860.31090.54710.077*
C12−0.34176 (16)0.2754 (4)0.65778 (19)0.0561 (6)
H12A−0.38930.25490.70060.067*
C13−0.23490 (15)0.2716 (3)0.68736 (15)0.0430 (4)
H1O1−0.142 (2)0.238 (5)0.787 (2)0.077 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0521 (3)0.0677 (4)0.0399 (2)0.0004 (3)0.0130 (2)−0.0002 (2)
Cl20.0322 (2)0.0865 (5)0.0786 (4)−0.0046 (3)−0.0083 (2)0.0036 (3)
Cl30.0415 (3)0.1152 (6)0.0624 (4)0.0192 (3)0.0154 (2)−0.0023 (4)
O10.0452 (8)0.0715 (12)0.0537 (9)0.0035 (8)0.0128 (7)0.0064 (8)
N10.0303 (7)0.0408 (9)0.0400 (8)0.0040 (6)0.0037 (6)−0.0019 (7)
C10.0366 (8)0.0376 (10)0.0365 (8)−0.0005 (8)0.0054 (7)0.0016 (8)
C20.0388 (9)0.0464 (12)0.0407 (9)−0.0037 (8)−0.0044 (7)0.0007 (8)
C30.0300 (8)0.0448 (11)0.0518 (11)−0.0015 (8)−0.0036 (7)0.0060 (9)
C40.0319 (8)0.0509 (12)0.0459 (10)0.0077 (8)0.0070 (7)0.0037 (9)
C50.0337 (8)0.0502 (12)0.0379 (9)0.0065 (8)0.0012 (7)−0.0009 (8)
C60.0291 (7)0.0349 (9)0.0396 (9)0.0009 (7)0.0032 (6)0.0000 (7)
C70.0309 (8)0.0399 (10)0.0411 (9)0.0031 (7)0.0049 (7)−0.0029 (8)
C80.0305 (8)0.0391 (10)0.0460 (9)0.0031 (7)0.0020 (7)−0.0049 (8)
C90.0404 (10)0.0649 (15)0.0473 (10)0.0039 (10)−0.0016 (8)−0.0046 (10)
C100.0443 (11)0.0808 (19)0.0592 (13)0.0061 (11)−0.0114 (10)−0.0079 (13)
C110.0352 (10)0.0735 (18)0.0790 (17)0.0022 (11)−0.0098 (10)−0.0134 (14)
C120.0346 (9)0.0597 (15)0.0752 (15)−0.0016 (10)0.0109 (10)−0.0075 (12)
C130.0360 (9)0.0391 (11)0.0544 (11)0.0025 (8)0.0072 (8)−0.0047 (9)
Geometric parameters (Å, º) top
Cl1—C11.7292 (19)C5—H5A0.9300
Cl2—C31.7222 (18)C7—C81.452 (2)
Cl3—C41.726 (2)C7—H7A0.9300
O1—C131.345 (3)C8—C131.399 (3)
O1—H1O10.79 (3)C8—C91.401 (3)
N1—C71.278 (2)C9—C101.380 (3)
N1—C61.411 (2)C9—H9A0.9300
C1—C21.387 (2)C10—C111.383 (4)
C1—C61.393 (2)C10—H10A0.9300
C2—C31.384 (3)C11—C121.373 (4)
C2—H2A0.9300C11—H11A0.9300
C3—C41.386 (3)C12—C131.394 (3)
C4—C51.386 (2)C12—H12A0.9300
C5—C61.393 (2)
C13—O1—H1O1110 (2)N1—C7—H7A119.0
C7—N1—C6120.55 (16)C8—C7—H7A119.0
C2—C1—C6121.80 (17)C13—C8—C9119.42 (18)
C2—C1—Cl1118.76 (14)C13—C8—C7121.61 (18)
C6—C1—Cl1119.44 (13)C9—C8—C7118.97 (18)
C3—C2—C1119.14 (17)C10—C9—C8120.8 (2)
C3—C2—H2A120.4C10—C9—H9A119.6
C1—C2—H2A120.4C8—C9—H9A119.6
C2—C3—C4120.04 (17)C9—C10—C11119.0 (2)
C2—C3—Cl2118.70 (15)C9—C10—H10A120.5
C4—C3—Cl2121.26 (16)C11—C10—H10A120.5
C3—C4—C5120.32 (18)C12—C11—C10121.3 (2)
C3—C4—Cl3120.94 (15)C12—C11—H11A119.4
C5—C4—Cl3118.73 (15)C10—C11—H11A119.4
C4—C5—C6120.60 (17)C11—C12—C13120.4 (2)
C4—C5—H5A119.7C11—C12—H12A119.8
C6—C5—H5A119.7C13—C12—H12A119.8
C1—C6—C5118.01 (16)O1—C13—C12118.5 (2)
C1—C6—N1118.57 (16)O1—C13—C8122.39 (18)
C5—C6—N1123.37 (16)C12—C13—C8119.1 (2)
N1—C7—C8122.10 (17)
C6—C1—C2—C3−1.9 (3)C7—N1—C6—C1151.17 (19)
Cl1—C1—C2—C3178.45 (16)C7—N1—C6—C5−31.6 (3)
C1—C2—C3—C4−0.9 (3)C6—N1—C7—C8179.28 (17)
C1—C2—C3—Cl2179.37 (16)N1—C7—C8—C136.2 (3)
C2—C3—C4—C52.1 (3)N1—C7—C8—C9−174.2 (2)
Cl2—C3—C4—C5−178.18 (17)C13—C8—C9—C10−0.2 (4)
C2—C3—C4—Cl3−176.72 (17)C7—C8—C9—C10−179.7 (2)
Cl2—C3—C4—Cl33.0 (3)C8—C9—C10—C111.0 (4)
C3—C4—C5—C6−0.5 (3)C9—C10—C11—C12−0.8 (4)
Cl3—C4—C5—C6178.34 (16)C10—C11—C12—C13−0.3 (4)
C2—C1—C6—C53.4 (3)C11—C12—C13—O1−178.8 (2)
Cl1—C1—C6—C5−176.92 (15)C11—C12—C13—C81.1 (4)
C2—C1—C6—N1−179.22 (18)C9—C8—C13—O1179.0 (2)
Cl1—C1—C6—N10.5 (3)C7—C8—C13—O1−1.5 (3)
C4—C5—C6—C1−2.2 (3)C9—C8—C13—C12−0.9 (3)
C4—C5—C6—N1−179.41 (19)C7—C8—C13—C12178.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···N10.79 (3)1.94 (3)2.633 (2)146 (3)

Experimental details

Crystal data
Chemical formulaC13H8Cl3NO
Mr300.55
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)12.8847 (16), 6.9505 (9), 14.4265 (18)
β (°) 96.612 (2)
V (Å3)1283.4 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.70
Crystal size (mm)0.36 × 0.19 × 0.14
Data collection
DiffractometerBruker SMART APEXII DUO CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.785, 0.908
No. of measured, independent and
observed [I > 2σ(I)] reflections		10136, 3782, 2586
Rint0.027
(sin θ/λ)max (Å−1)0.708
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.124, 1.02
No. of reflections3782
No. of parameters167
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.45, −0.44

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SAINT (Bruker, 2009, SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···N10.79 (3)1.94 (3)2.633 (2)146 (3)
 

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
 First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationBhat, M. A., Imran, M., Khan, S. A. & Siddiqui, N. (2005). J. Pharm. Sci. 67, 151–159.  CAS Google Scholar
 First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFun, H.-K., Quah, C. K., Viveka, S., Madhukumar, D. J. & Nagaraja, G. K. (2011a). Acta Cryst. E67, o1933.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationFun, H.-K., Quah, C. K., Viveka, S., Madhukumar, D. J. & Prasad, D. J. (2011b). Acta Cryst. E67, o1932.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationPandey, S. N., Lakshmi, V. S. & Pandey, A. (2003). Indian J. Pharm. Sci. 65, 213–222.  Google Scholar
 First citationShapiro, H. K. (1998). Am. J. Ther. 5, 323–353.  CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationVenugopal, K. N. & Jayashree, B. S. (2008). Indian J. Pharm. Sci. 70, 88–91.  Web of Science PubMed Google Scholar
 First citationVillar, R., Encio, I., Migliaccio, M., Gil, M. G. & Martinez-Merino, V. (2004). Bioorg. Med. Chem. 12, 963–968.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationWadher, S. J., Puranik, M. P., Karande, N. A. & Yeole, P. G. (2009). Int. J. PharmTech Res. 1, 22–33.  CAS 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 67| Part 8| August 2011| Page o1934
doi:10.1107/S1600536811026122
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