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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 64| Part 3| March 2008| Page o603
doi:10.1107/S1600536808002626

N-(2-Meth­oxy­phen­yl)-2-nitro­benzamide

Aamer Saeed,a* Shahid Hussaina and Michael Bolteb

aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, and bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
*Correspondence e-mail: aamersaeed@yahoo.com

(Received 3 November 2007; accepted 23 January 2008; online 20 February 2008)

Geometric parameters of the title compound, C14H12N2O4, are in the usual ranges. The dihedral angle between the two aromatic rings is 28.9 (1)°. The nitro group is twisted by 40.2 (1)° out of the plane of the aromatic ring to which it is attached. The crystal structure is stabilized by an N—H⋯O hydrogen bond.

Related literature

For related literature, see: Capdeville et al. (2002[Capdeville, R., Buchdunger, E., Zimmermann, J. & Matter, A. (2002). Nat. Rev. Drug Discov. 1, 493-502.]); Ho et al. (2002[Ho, T.-I., Chen, W.-S., Hsu, C.-W., Tsai, Y.-M. & Fang, J.-M. (2002). Heterocycles, 57, 1501-1506.]); Igawa et al. (1999[Igawa, H., Nishimura, M., Okada, K. & Nakamura, T. (1999). Japan Patent 11171848.]); Jackson et al. (1994[Jackson, S., DeGrado, W., Dwivedi, A., Parthasarathy, A., Higley, A., Krywko, J., Rockwell, A., Markwalder, J., Wells, G., Wexler, R., Mousa, S. & Harlow, R. (1994). J. Am. Chem. Soc. 116, 3220-3230.]); Makino et al. (2001[Makino, S., Suzuki, N., Nakanishi, E. & Tsuji, T. (2001). Synlett, pp. 333-336.], 2003[Makino, S., Nakanishi, E. & Tsuji, T. (2003). Bull. Korean Chem. Soc. 24, 389-392.]); Manley et al. (2002[Manley, P. W., Furet, P., Bold, G., Brüggen, J., Mestan, J., Meyer, T., Schnell, C. R. & Wood, J. (2002). J. Med. Chem. 45, 5687-5693.]); Zhichkin et al. (2007[Zhichkin, P., Kesicki, E., Treiberg, J., Bourdon, L., Ronsheim, M., Ooi, H. C., White, S., Judkins, A. & Fairfax, D. (2007). Org. Lett. 9, 1415-1418.]).

[Scheme 1]

Experimental

Crystal data

  • C14H12N2O4

  • Mr = 272.26

  • Orthorhombic, P 21 21 21

  • a = 7.6467 (11) Å

  • b = 9.9272 (8) Å

  • c = 16.5032 (14) Å

  • V = 1252.8 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 173 (2) K

  • 0.37 × 0.33 × 0.21 mm
Data collection

  • Stoe IPDSII two-circle diffractometer

  • Absorption correction: none

  • 8342 measured reflections

  • 1368 independent reflections

  • 1275 reflections with I > 2σ(I)

  • Rint = 0.042
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.110

  • S = 1.05

  • 1368 reflections

  • 187 parameters

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

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O2i 0.82 (4) 2.57 (4) 3.352 (3) 159 (3)
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; 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, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002626/ez2111sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808002626/ez2111Isup2.hkl

checkCIF report


Comment top

The benzanilide core is present in compounds with such a wide range of biological activities that it has been called a privileged structure. Benzanilides serve as intermediates to benzothiadiazin-4-ones (Makino et al., 2003), quinazoline-2,4-diones (Makino et al., 2001), benzodiazepine-2,5-diones (Ho et al., 2002) and 2,3-disubstituted 3H-quinazoline-4-ones (Zhichkin et al., 2007). Benzanilides have established their efficacy as central elements of ligands that bind to a wide variety of receptor types. Thus a benzanilide containing aminoalkyl groups originally designed as a peptidomimetic has been incorporated in an Arg-Gly-Asp cyclic peptide yielding a high affinity GPIIb/IIIa ligand (Jackson et al., 1994). Imatinib is an ATP-site binding kinase inhibitor and platelet-derived growth factor receptor kinases (Capdeville et al., 2002). Pyridylmethyl containing benzanilides are vascular endothelial growth factor receptors and tyrosine kinase inhibitors (Manley et al., 2002). Furthermore, benzamides have been reported to have activities as acetyl-CoA carboxylase and farnesyl transferase inhibitors (Igawa et al., 1999)

Geometric parameters of the title compound, C14H12N2O4, are in the usual ranges. The dihedral angle between the two aromatic rings is 28.9 (1)°. The nitrogroup is twisted by 40.2 (1)° out of the plane of the phenyl ring to which it is attached. The crystal structure is stabilized by an N—H···O hydrogen bond.

Related literature top

For related literature, see: Capdeville et al. (2002); Ho et al. (2002); Igawa et al. (1999); Jackson et al. (1994); Makino et al. (2001, 2003); Manley et al. (2002); Zhichkin et al. (2007).

Experimental top

A mixture of 2-methoxyaniline (10.0 g, 65.7 mmol), 2-nitrobenzoyl chloride (10 ml, 86.9 mmol), and pyridine (20 ml) was left at 25 °C for 15 h. Water (100 ml) was then added, and the resulting precipitate was collected. Recrystallization of the precipitate from benzene gave 12.6 g (75%) of the title compound as yellow blocks: mp 95–96 °C 1H NMR (CDCl3) δ 7.23–8.30 (m, 8H, Ar—Hs), 11.36 (br s, 1H, NH).

Refinement top

In the absence of anomalous scatterers, Friedel pairs had been merged and the absolute structure was arbitrarily assigned. All H atoms were found in a difference map, but those bonded to C were geometrically positioned and refined with fixed individual displacement parameters [U(H) = 1.2 Ueq(C) or U(H) = 1.5 Ueq(Cmethyl)] using a riding model with C—H = 0.95Å or C—H = 0.98Å for aromatic and methyl C, respectively. The methyl group was allowed to rotate, but not to tip. The amino H atom was freely refined.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound.
N-(2-Methoxyphenyl)-2-nitrobenzamide top
Crystal data top
C14H12N2O4Dx = 1.444 Mg m−3
Mr = 272.26Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 7856 reflections
a = 7.6467 (11) Åθ = 3.8–25.6°
b = 9.9272 (8) ŵ = 0.11 mm−1
c = 16.5032 (14) ÅT = 173 K
V = 1252.8 (2) Å3Block, light yellow
Z = 40.37 × 0.33 × 0.21 mm
F(000) = 568
Data collection top
Stoe IPDSII two-circle
diffractometer		1275 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.042
Graphite monochromatorθmax = 25.6°, θmin = 3.6°
ω scansh = −7→9
8342 measured reflectionsk = −12→12
1368 independent reflectionsl = −20→18
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)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0824P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1368 reflectionsΔρmax = 0.28 e Å−3
187 parametersΔρmin = −0.21 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: 0.052 (7)
Crystal data top
C14H12N2O4V = 1252.8 (2) Å3
Mr = 272.26Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.6467 (11) ŵ = 0.11 mm−1
b = 9.9272 (8) ÅT = 173 K
c = 16.5032 (14) Å0.37 × 0.33 × 0.21 mm
Data collection top
Stoe IPDSII two-circle
diffractometer		1275 reflections with I > 2σ(I)
8342 measured reflectionsRint = 0.042
1368 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.28 e Å−3
1368 reflectionsΔρmin = −0.21 e Å−3
187 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
C10.7040 (3)0.4189 (2)0.58905 (15)0.0271 (5)
N10.6935 (3)0.46807 (19)0.51339 (14)0.0287 (5)
H10.618 (5)0.449 (3)0.4799 (19)0.040 (9)*
N20.7600 (3)0.14453 (18)0.64422 (13)0.0299 (5)
O10.8235 (3)0.44489 (17)0.63779 (11)0.0370 (5)
O20.8450 (3)0.16188 (18)0.58190 (13)0.0410 (5)
O30.8114 (3)0.07915 (18)0.70333 (13)0.0419 (5)
O40.5752 (2)0.62521 (16)0.39737 (11)0.0305 (5)
C110.5537 (3)0.3307 (2)0.61508 (14)0.0263 (5)
C120.5833 (3)0.2030 (2)0.64870 (16)0.0264 (5)
C130.4498 (4)0.1261 (2)0.68256 (15)0.0307 (6)
H130.47440.04040.70550.037*
C140.2795 (4)0.1764 (2)0.68236 (17)0.0338 (6)
H140.18690.12480.70490.041*
C150.2456 (4)0.3028 (3)0.64891 (17)0.0360 (6)
H150.12940.33680.64830.043*
C160.3821 (4)0.3800 (2)0.61615 (17)0.0324 (6)
H160.35790.46670.59450.039*
C210.8150 (3)0.5560 (2)0.47494 (14)0.0260 (5)
C220.7505 (3)0.6385 (2)0.41263 (15)0.0267 (5)
C230.8635 (4)0.7254 (2)0.37131 (16)0.0293 (6)
H230.81990.78250.32970.035*
C241.0410 (4)0.7277 (2)0.39163 (16)0.0314 (6)
H241.11770.78720.36380.038*
C251.1068 (4)0.6440 (2)0.45211 (17)0.0323 (6)
H251.22800.64520.46490.039*
C260.9933 (4)0.5579 (2)0.49399 (15)0.0299 (5)
H261.03740.50070.53540.036*
C270.5074 (4)0.6982 (2)0.32917 (16)0.0323 (6)
H27A0.52110.79510.33850.048*
H27B0.38310.67690.32220.048*
H27C0.57170.67240.28020.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0227 (13)0.0256 (10)0.0331 (13)0.0022 (9)−0.0009 (10)−0.0013 (9)
N10.0195 (11)0.0312 (10)0.0354 (12)−0.0040 (8)−0.0015 (10)0.0024 (8)
N20.0261 (12)0.0246 (9)0.0390 (12)0.0014 (9)−0.0020 (9)−0.0034 (8)
O10.0324 (11)0.0415 (9)0.0372 (10)−0.0095 (9)−0.0085 (8)0.0057 (8)
O20.0308 (11)0.0429 (9)0.0491 (11)0.0067 (8)0.0110 (9)0.0029 (9)
O30.0413 (12)0.0373 (8)0.0470 (12)0.0104 (9)−0.0093 (9)0.0037 (8)
O40.0209 (9)0.0330 (8)0.0374 (10)−0.0019 (7)−0.0012 (8)0.0062 (7)
C110.0217 (12)0.0282 (11)0.0289 (12)0.0003 (10)−0.0005 (11)0.0009 (9)
C120.0208 (14)0.0269 (10)0.0315 (12)−0.0008 (9)0.0007 (10)−0.0038 (9)
C130.0312 (15)0.0271 (10)0.0338 (13)−0.0040 (10)0.0025 (12)−0.0029 (9)
C140.0268 (15)0.0368 (12)0.0377 (14)−0.0069 (11)0.0047 (12)−0.0027 (10)
C150.0216 (14)0.0457 (13)0.0408 (15)0.0011 (11)0.0024 (12)−0.0023 (11)
C160.0255 (14)0.0355 (12)0.0362 (13)0.0055 (10)0.0001 (12)0.0043 (10)
C210.0216 (12)0.0247 (10)0.0315 (12)−0.0026 (10)0.0041 (10)0.0000 (9)
C220.0210 (12)0.0261 (10)0.0328 (12)−0.0010 (9)0.0016 (10)−0.0011 (9)
C230.0270 (14)0.0264 (10)0.0345 (13)−0.0007 (10)0.0036 (11)0.0005 (9)
C240.0247 (14)0.0304 (11)0.0390 (14)−0.0047 (10)0.0044 (12)−0.0004 (10)
C250.0225 (13)0.0345 (12)0.0398 (13)−0.0043 (11)−0.0005 (11)−0.0034 (10)
C260.0243 (13)0.0328 (12)0.0326 (12)0.0005 (11)−0.0010 (10)−0.0008 (9)
C270.0240 (14)0.0362 (12)0.0367 (14)0.0010 (10)−0.0036 (11)0.0074 (9)
Geometric parameters (Å, º) top
C1—O11.244 (3)C15—C161.404 (4)
C1—N11.343 (3)C15—H150.9500
C1—C111.508 (3)C16—H160.9500
N1—C211.424 (3)C21—C261.399 (4)
N1—H10.82 (4)C21—C221.404 (3)
N2—O21.229 (3)C22—C231.399 (3)
N2—O31.236 (3)C23—C241.399 (4)
N2—C121.473 (3)C23—H230.9500
O4—C221.371 (3)C24—C251.393 (4)
O4—C271.435 (3)C24—H240.9500
C11—C161.400 (4)C25—C261.401 (4)
C11—C121.402 (3)C25—H250.9500
C12—C131.392 (4)C26—H260.9500
C13—C141.395 (4)C27—H27A0.9800
C13—H130.9500C27—H27B0.9800
C14—C151.395 (4)C27—H27C0.9800
C14—H140.9500
O1—C1—N1124.7 (2)C11—C16—H16119.6
O1—C1—C11119.7 (2)C15—C16—H16119.6
N1—C1—C11115.5 (2)C26—C21—C22119.9 (2)
C1—N1—C21126.7 (2)C26—C21—N1122.9 (2)
C1—N1—H1126 (2)C22—C21—N1117.1 (2)
C21—N1—H1107 (2)O4—C22—C23125.0 (2)
O2—N2—O3124.5 (2)O4—C22—C21115.0 (2)
O2—N2—C12118.2 (2)C23—C22—C21120.0 (2)
O3—N2—C12117.3 (2)C22—C23—C24119.5 (2)
C22—O4—C27116.69 (19)C22—C23—H23120.2
C16—C11—C12117.5 (2)C24—C23—H23120.2
C16—C11—C1121.0 (2)C25—C24—C23120.8 (2)
C12—C11—C1121.0 (2)C25—C24—H24119.6
C13—C12—C11122.5 (2)C23—C24—H24119.6
C13—C12—N2118.5 (2)C24—C25—C26119.6 (3)
C11—C12—N2119.0 (2)C24—C25—H25120.2
C12—C13—C14119.1 (2)C26—C25—H25120.2
C12—C13—H13120.4C21—C26—C25120.1 (2)
C14—C13—H13120.4C21—C26—H26120.0
C13—C14—C15119.8 (2)C25—C26—H26120.0
C13—C14—H14120.1O4—C27—H27A109.5
C15—C14—H14120.1O4—C27—H27B109.5
C14—C15—C16120.3 (3)H27A—C27—H27B109.5
C14—C15—H15119.8O4—C27—H27C109.5
C16—C15—H15119.8H27A—C27—H27C109.5
C11—C16—C15120.7 (2)H27B—C27—H27C109.5
O1—C1—N1—C210.8 (4)C12—C11—C16—C15−0.8 (4)
C11—C1—N1—C21178.3 (2)C1—C11—C16—C15−172.8 (2)
O1—C1—C11—C16118.2 (3)C14—C15—C16—C111.2 (4)
N1—C1—C11—C16−59.5 (3)C1—N1—C21—C2629.1 (4)
O1—C1—C11—C12−53.6 (3)C1—N1—C21—C22−154.1 (2)
N1—C1—C11—C12128.8 (2)C27—O4—C22—C235.6 (3)
C16—C11—C12—C13−0.2 (4)C27—O4—C22—C21−174.3 (2)
C1—C11—C12—C13171.8 (2)C26—C21—C22—O4177.9 (2)
C16—C11—C12—N2176.4 (2)N1—C21—C22—O41.0 (3)
C1—C11—C12—N2−11.6 (3)C26—C21—C22—C23−2.0 (3)
O2—N2—C12—C13138.0 (3)N1—C21—C22—C23−178.8 (2)
O3—N2—C12—C13−40.8 (3)O4—C22—C23—C24−178.8 (2)
O2—N2—C12—C11−38.8 (3)C21—C22—C23—C241.1 (4)
O3—N2—C12—C11142.4 (2)C22—C23—C24—C250.4 (4)
C11—C12—C13—C140.8 (4)C23—C24—C25—C26−1.0 (4)
N2—C12—C13—C14−175.8 (2)C22—C21—C26—C251.3 (4)
C12—C13—C14—C15−0.4 (4)N1—C21—C26—C25178.0 (2)
C13—C14—C15—C16−0.6 (4)C24—C25—C26—C210.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.82 (4)2.57 (4)3.352 (3)159 (3)
Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formulaC14H12N2O4
Mr272.26
Crystal system, space groupOrthorhombic, P212121
Temperature (K)173
a, b, c (Å)7.6467 (11), 9.9272 (8), 16.5032 (14)
V (Å3)1252.8 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.37 × 0.33 × 0.21
Data collection
DiffractometerStoe IPDSII two-circle
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		8342, 1368, 1275
Rint0.042
(sin θ/λ)max (Å−1)0.608
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.110, 1.05
No. of reflections1368
No. of parameters187
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.28, −0.21

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.82 (4)2.57 (4)3.352 (3)159 (3)
Symmetry code: (i) x−1/2, −y+1/2, −z+1.
 

Acknowledgements

AS gratefully acknowledges a research grant from Quaid-i-Azam University, Islamabad.

References

First citationCapdeville, R., Buchdunger, E., Zimmermann, J. & Matter, A. (2002). Nat. Rev. Drug Discov. 1, 493–502.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationHo, T.-I., Chen, W.-S., Hsu, C.-W., Tsai, Y.-M. & Fang, J.-M. (2002). Heterocycles, 57, 1501–1506.  CrossRef CAS Google Scholar
 First citationIgawa, H., Nishimura, M., Okada, K. & Nakamura, T. (1999). Japan Patent 11171848.  Google Scholar
 First citationJackson, S., DeGrado, W., Dwivedi, A., Parthasarathy, A., Higley, A., Krywko, J., Rockwell, A., Markwalder, J., Wells, G., Wexler, R., Mousa, S. & Harlow, R. (1994). J. Am. Chem. Soc. 116, 3220–3230.  CSD CrossRef CAS Web of Science Google Scholar
 First citationMakino, S., Nakanishi, E. & Tsuji, T. (2003). Bull. Korean Chem. Soc. 24, 389–392.  CAS Google Scholar
 First citationMakino, S., Suzuki, N., Nakanishi, E. & Tsuji, T. (2001). Synlett, pp. 333–336.  Google Scholar
 First citationManley, P. W., Furet, P., Bold, G., Brüggen, J., Mestan, J., Meyer, T., Schnell, C. R. & Wood, J. (2002). J. Med. Chem. 45, 5687–5693.  Web of Science 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. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationStoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.  Google Scholar
 First citationZhichkin, P., Kesicki, E., Treiberg, J., Bourdon, L., Ronsheim, M., Ooi, H. C., White, S., Judkins, A. & Fairfax, D. (2007). Org. Lett. 9, 1415–1418.  Web of Science CrossRef PubMed CAS Google Scholar

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ISSN: 2056-9890
Volume 64| Part 3| March 2008| Page o603
doi:10.1107/S1600536808002626
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