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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 65| Part 6| June 2009| Page o1334
doi:10.1107/S1600536809018236

4-Chloro-N-m-tolyl­benzamide

Aamer Saeed,a* Madiha Irfana and Michael Bolteb

aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, 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 7 May 2009; accepted 14 May 2009; online 20 May 2009)

In the title compound, C14H12ClNO, the dihedral angle between the two aromatic rings is 11.29 (15)°. The crystal packing is stabilized by N—H⋯O hydrogen bonds linking the mol­ecules into chains running along the c axis.

Related literature

For the biological activity of N-substituted benzamides and benzanilide derivatives, see Calderone et al. (2006[Calderone, V., Fiamingo, F. L., Giorgi, I., Leonardi, M., Livi, O., Martelli, A. & Martinotti, E. (2006). Eur. J. Med. Chem. 41, 761-767.]); Beccalli et al. (2005[Beccalli, E. M., Broggini, G., Paladinoa, G. & Zonia, C. (2005). Tetrahedron, 61, 61-68.]); Yoo et al. (2005[Yoo, C. L., Fettinger, J. C. & Kurth, M. J. (2005). J. Org. Chem. 70, 6941-6943.]); Vega-Noverola et al. (1989[Vega-Noverola, A. P., Soto, J. M., Noguera, F. P., Mauri, J. M. & Spickett, G. W. R. (1989). US Patent No. 4 877 780.]); Olsson et al. (2002[Olsson, A. R., Lindgren, H., Pero, R. W. & Leanderson, T. (2002). Br. J. Cancer, 86, 971-978.]); Lindgren et al. (2001[Lindgren, H., Pero, R. W., Ivars, F. & Leanderson, T. (2001). Mol. Immunol. 38, 267-277.]); 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.]). For related structures see: Saeed et al. (2008[Saeed, A., Khera, R. A., Abbas, N., Simpson, J. & Stanley, R. G. (2008). Acta Cryst. E64, o2322-o2323.]); Chopra & Guru Row (2008[Chopra, D. & Guru Row, T. N. (2008). CrystEngComm, 10, 54-67.]); Donnelly et al. (2008[Donnelly, K., Gallagher, J. F. & Lough, A. J. (2008). Acta Cryst. C64, o335-o340.])

[Scheme 1]

Experimental

Crystal data

  • C14H12ClNO

  • Mr = 245.70

  • Monoclinic, P 21 /c

  • a = 13.9721 (14) Å

  • b = 10.1922 (6) Å

  • c = 9.0154 (8) Å

  • β = 105.415 (7)°

  • V = 1237.67 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.29 mm−1

  • T = 173 K

  • 0.26 × 0.24 × 0.23 mm
Data collection

  • Stoe IPDSII two-circle diffractometer

  • Absorption correction: multi-scan (MULABS; Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.928, Tmax = 0.936

  • 9469 measured reflections

  • 2193 independent reflections

  • 1787 reflections with I > 2σ(I)

  • Rint = 0.074
Refinement

  • R[F2 > 2σ(F2)] = 0.066

  • wR(F2) = 0.178

  • S = 1.04

  • 2193 reflections

  • 160 parameters

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

  • Δρmax = 0.51 e Å−3

  • Δρmin = −0.47 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O1i 0.88 (3) 1.99 (3) 2.854 (3) 166 (3)
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

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, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018236/ya2096sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809018236/ya2096Isup2.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. N-Substituted benzamides are well known anticancer compounds and the mechanism of action for N-substituted benzamide-induced apoptosis has been studied, using declopramide as a lead compound (Olsson et al., 2002). N-Substituted benzamides inhibit the activity of nuclear factor- B and nuclear factor of activated T cells activity while inducing activator protein 1 activity in T lymphocytes (Lindgren et al., 2001). Various N-substituted benzamides exhibit potent antiemetic activity (Vega-Noverola et al., 1989), while heterocyclic analogs of benzanilide derivatives are potassium channel activators (Calderone et al., 2006). o-Aryloxylation of N-substituted benzamides induced by the copper(II)/trimethylamine N-oxide system has been studied. N-Alkylated 2-nitrobenzamides are intermediates in the synthesis of dibenzo[b,e][1,4]diazepines (Zhichkin et al., 2007) and N-Acyl-2-nitrobenzamides are precursors of 2,3-disubstitued 3H-quinazoline-4-ones (Beccalli et al., 2005). A one-pot conversion of 2-nitro-n-arylbenzamides to 2,3-dihydro-1H-quinazoline-4-ones has also been reported (Yoo et al., 2005). As part of our work on the structure of benzanilides and related compounds, we report here the structure of the title 4-chlorobenzamide derivative, I, Fig 1.

The dihedral angle between the two aromatic rings is 11.29 (15) °. The crystal packing is stabilized by N—H···O hydrogen bonds linking the molecules to chains running along the c axis.

Related literature top

For the biological activity of N-substituted benzamides and benzanilide derivatives, see Calderone et al. (2006); Beccalli et al. (2005); Yoo et al. (2005); Vega-Noverola et al. (1989); Olsson et al. (2002); Lindgren et al. (2001); Zhichkin et al. (2007). For related structures see: Saeed et al. (2008); Chopra & Guru Row (2008); Donnelly et al. (2008)

Experimental top

4-Chlorobenzoyl chloride (5.4 mmol) in CHCl3 was treated with 3-methylaniline (21.6 mmol) under a nitrogen atmosphere at reflux for 3 h. Upon cooling, the reaction mixture was diluted with CHCl3 and washed consecutively with aq 1 M HCl and saturated aq NaHCO3. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Crystallization of the residue from CHCl3 afforded the title compound (81%) as colourless blocks. Anal. calcd. for C14H12ClNO1: C 68.44, H 4.92, N 5.70%; found: C 68.39, H 4.90, N 5.67%

Refinement top

H atoms were located in a difference map but those bonded to C were geometrically positioned and refined using a riding model with fixed individual displacement parameters [U(H) = 1.2 Ueq(C) or U(H) = 1.5 Ueq(Cmethyl)] and C—H(aromatic) = 0.95Å or C—H(methyl) = 0.98 Å, respectively. The H atom bonded to N was refined isotropically, N-H 0.88 (3) Å.

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, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Perspective view of the title compound with the atom numbering scheme; displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radii.
4-Chloro-N-m-tolylbenzamide top
Crystal data top
C14H12ClNOF(000) = 512
Mr = 245.70Dx = 1.319 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10353 reflections
a = 13.9721 (14) Åθ = 2.6–27.8°
b = 10.1922 (6) ŵ = 0.29 mm−1
c = 9.0154 (8) ÅT = 173 K
β = 105.415 (7)°Block, colourless
V = 1237.67 (18) Å30.26 × 0.24 × 0.23 mm
Z = 4
Data collection top
Stoe IPDSII two-circle
diffractometer		2193 independent reflections
Radiation source: fine-focus sealed tube1787 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(MULABS; Spek, 2009; Blessing, 1995)		h = −16→16
Tmin = 0.928, Tmax = 0.936k = −12→12
9469 measured reflectionsl = −10→10
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)] = 0.066H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.178 w = 1/[σ2(Fo2) + (0.1231P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2193 reflectionsΔρmax = 0.51 e Å−3
160 parametersΔρmin = −0.47 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: 0.018 (5)
Crystal data top
C14H12ClNOV = 1237.67 (18) Å3
Mr = 245.70Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.9721 (14) ŵ = 0.29 mm−1
b = 10.1922 (6) ÅT = 173 K
c = 9.0154 (8) Å0.26 × 0.24 × 0.23 mm
β = 105.415 (7)°
Data collection top
Stoe IPDSII two-circle
diffractometer		2193 independent reflections
Absorption correction: multi-scan
(MULABS; Spek, 2009; Blessing, 1995)		1787 reflections with I > 2σ(I)
Tmin = 0.928, Tmax = 0.936Rint = 0.074
9469 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0660 restraints
wR(F2) = 0.178H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.51 e Å−3
2193 reflectionsΔρmin = −0.47 e Å−3
160 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
Cl10.86033 (5)0.92615 (6)0.74007 (9)0.0588 (3)
O10.41731 (13)0.85570 (16)0.23364 (18)0.0439 (5)
N10.38823 (16)0.72470 (18)0.4215 (2)0.0393 (5)
H10.408 (2)0.702 (2)0.519 (3)0.041 (7)*
C10.44505 (17)0.80750 (19)0.3639 (3)0.0366 (5)
C110.54665 (18)0.83650 (19)0.4646 (3)0.0371 (6)
C120.59229 (19)0.7638 (2)0.5951 (3)0.0435 (6)
H120.55740.69300.62530.052*
C130.68742 (19)0.7929 (2)0.6814 (3)0.0456 (6)
H130.71720.74340.77110.055*
C140.73903 (18)0.8948 (2)0.6362 (3)0.0422 (6)
C150.69544 (19)0.9691 (2)0.5060 (3)0.0413 (6)
H150.73111.03870.47530.050*
C160.6000 (2)0.94034 (19)0.4222 (3)0.0398 (6)
H160.56970.99170.33430.048*
C210.29378 (19)0.6714 (2)0.3444 (3)0.0388 (6)
C220.22613 (19)0.7341 (2)0.2241 (3)0.0404 (6)
H220.24260.81660.18840.049*
C230.13421 (19)0.6770 (2)0.1555 (3)0.0429 (6)
C240.1115 (2)0.5552 (2)0.2080 (3)0.0468 (6)
H240.04990.51420.16050.056*
C250.1784 (2)0.4941 (2)0.3291 (3)0.0488 (6)
H250.16180.41180.36510.059*
C260.2693 (2)0.5508 (2)0.3988 (3)0.0452 (6)
H260.31450.50840.48260.054*
C270.0604 (2)0.7461 (3)0.0252 (3)0.0561 (7)
H27A0.07200.7202−0.07320.084*
H27B0.06860.84130.03830.084*
H27C−0.00730.72160.02640.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0465 (5)0.0523 (5)0.0671 (6)−0.0050 (3)−0.0031 (4)−0.0004 (3)
O10.0528 (11)0.0441 (9)0.0317 (9)−0.0007 (7)0.0059 (8)0.0023 (7)
N10.0477 (12)0.0352 (9)0.0296 (11)−0.0020 (8)0.0009 (9)0.0012 (8)
C10.0479 (14)0.0276 (10)0.0321 (12)0.0042 (9)0.0067 (10)−0.0024 (8)
C110.0481 (14)0.0277 (10)0.0340 (12)0.0040 (9)0.0081 (11)−0.0020 (8)
C120.0481 (15)0.0363 (11)0.0433 (14)−0.0019 (10)0.0070 (12)0.0059 (10)
C130.0485 (15)0.0391 (12)0.0435 (14)0.0040 (11)0.0021 (12)0.0106 (10)
C140.0441 (14)0.0334 (11)0.0458 (14)0.0025 (10)0.0062 (12)−0.0051 (10)
C150.0522 (14)0.0306 (11)0.0409 (13)−0.0014 (10)0.0119 (12)−0.0010 (9)
C160.0539 (15)0.0283 (10)0.0345 (13)0.0020 (9)0.0070 (11)−0.0005 (9)
C210.0468 (13)0.0322 (11)0.0343 (12)−0.0028 (9)0.0053 (11)−0.0059 (9)
C220.0487 (14)0.0343 (11)0.0358 (13)−0.0011 (9)0.0069 (11)−0.0032 (9)
C230.0471 (14)0.0448 (13)0.0350 (13)−0.0002 (10)0.0080 (11)−0.0066 (10)
C240.0490 (15)0.0410 (12)0.0478 (15)−0.0060 (10)0.0081 (12)−0.0116 (10)
C250.0566 (15)0.0357 (12)0.0523 (15)−0.0047 (11)0.0111 (13)−0.0041 (10)
C260.0546 (16)0.0336 (11)0.0432 (14)−0.0011 (10)0.0058 (12)−0.0013 (9)
C270.0510 (17)0.0587 (15)0.0500 (16)−0.0056 (12)−0.0017 (13)0.0034 (12)
Geometric parameters (Å, º) top
Cl1—C141.734 (3)C16—H160.9500
O1—C11.236 (3)C21—C221.390 (3)
N1—C11.353 (3)C21—C261.398 (3)
N1—C211.426 (3)C22—C231.396 (3)
N1—H10.88 (3)C22—H220.9500
C1—C111.497 (3)C23—C241.394 (3)
C11—C121.393 (3)C23—C271.515 (4)
C11—C161.404 (3)C24—C251.383 (4)
C12—C131.382 (4)C24—H240.9500
C12—H120.9500C25—C261.385 (4)
C13—C141.386 (4)C25—H250.9500
C13—H130.9500C26—H260.9500
C14—C151.393 (3)C27—H27A0.9800
C15—C161.378 (4)C27—H27B0.9800
C15—H150.9500C27—H27C0.9800
C1—N1—C21127.7 (2)C22—C21—C26119.9 (2)
C1—N1—H1119.2 (18)C22—C21—N1123.7 (2)
C21—N1—H1112.9 (18)C26—C21—N1116.4 (2)
O1—C1—N1123.0 (2)C21—C22—C23120.6 (2)
O1—C1—C11120.3 (2)C21—C22—H22119.7
N1—C1—C11116.7 (2)C23—C22—H22119.7
C12—C11—C16118.3 (2)C24—C23—C22119.1 (2)
C12—C11—C1123.7 (2)C24—C23—C27120.5 (2)
C16—C11—C1118.0 (2)C22—C23—C27120.4 (2)
C13—C12—C11121.1 (2)C25—C24—C23120.1 (2)
C13—C12—H12119.4C25—C24—H24119.9
C11—C12—H12119.4C23—C24—H24119.9
C12—C13—C14119.5 (2)C24—C25—C26121.1 (2)
C12—C13—H13120.2C24—C25—H25119.5
C14—C13—H13120.2C26—C25—H25119.5
C13—C14—C15120.6 (2)C25—C26—C21119.2 (2)
C13—C14—Cl1119.28 (19)C25—C26—H26120.4
C15—C14—Cl1120.04 (19)C21—C26—H26120.4
C16—C15—C14119.3 (2)C23—C27—H27A109.5
C16—C15—H15120.4C23—C27—H27B109.5
C14—C15—H15120.4H27A—C27—H27B109.5
C15—C16—C11121.2 (2)C23—C27—H27C109.5
C15—C16—H16119.4H27A—C27—H27C109.5
C11—C16—H16119.4H27B—C27—H27C109.5
C21—N1—C1—O15.0 (4)C12—C11—C16—C150.8 (3)
C21—N1—C1—C11−173.24 (19)C1—C11—C16—C15−177.3 (2)
O1—C1—C11—C12−164.2 (2)C1—N1—C21—C22−28.5 (4)
N1—C1—C11—C1214.2 (3)C1—N1—C21—C26153.4 (2)
O1—C1—C11—C1613.8 (3)C26—C21—C22—C23−0.9 (4)
N1—C1—C11—C16−167.84 (19)N1—C21—C22—C23−179.0 (2)
C16—C11—C12—C130.2 (4)C21—C22—C23—C24−0.7 (4)
C1—C11—C12—C13178.2 (2)C21—C22—C23—C27179.5 (2)
C11—C12—C13—C14−1.0 (4)C22—C23—C24—C251.6 (4)
C12—C13—C14—C150.9 (4)C27—C23—C24—C25−178.6 (3)
C12—C13—C14—Cl1−177.17 (19)C23—C24—C25—C26−1.0 (4)
C13—C14—C15—C160.1 (4)C24—C25—C26—C21−0.6 (4)
Cl1—C14—C15—C16178.14 (18)C22—C21—C26—C251.5 (4)
C14—C15—C16—C11−1.0 (4)N1—C21—C26—C25179.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.88 (3)1.99 (3)2.854 (3)166 (3)
Symmetry code: (i) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC14H12ClNO
Mr245.70
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)13.9721 (14), 10.1922 (6), 9.0154 (8)
β (°) 105.415 (7)
V (Å3)1237.67 (18)
Z4
Radiation typeMo Kα
µ (mm−1)0.29
Crystal size (mm)0.26 × 0.24 × 0.23
Data collection
DiffractometerStoe IPDSII two-circle
diffractometer
Absorption correctionMulti-scan
(MULABS; Spek, 2009; Blessing, 1995)
Tmin, Tmax0.928, 0.936
No. of measured, independent and
observed [I > 2σ(I)] reflections		9469, 2193, 1787
Rint0.074
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.178, 1.04
No. of reflections2193
No. of parameters160
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.51, −0.47

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.88 (3)1.99 (3)2.854 (3)166 (3)
Symmetry code: (i) x, −y+3/2, z+1/2.
 

References

First citationBeccalli, E. M., Broggini, G., Paladinoa, G. & Zonia, C. (2005). Tetrahedron, 61, 61–68.  Web of Science CrossRef CAS Google Scholar
 First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–38.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationCalderone, V., Fiamingo, F. L., Giorgi, I., Leonardi, M., Livi, O., Martelli, A. & Martinotti, E. (2006). Eur. J. Med. Chem. 41, 761–767.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationChopra, D. & Guru Row, T. N. (2008). CrystEngComm, 10, 54–67.  Web of Science CSD CrossRef CAS Google Scholar
 First citationDonnelly, K., Gallagher, J. F. & Lough, A. J. (2008). Acta Cryst. C64, o335–o340.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationLindgren, H., Pero, R. W., Ivars, F. & Leanderson, T. (2001). Mol. Immunol. 38, 267–277.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationOlsson, A. R., Lindgren, H., Pero, R. W. & Leanderson, T. (2002). Br. J. Cancer, 86, 971–978.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSaeed, A., Khera, R. A., Abbas, N., Simpson, J. & Stanley, R. G. (2008). Acta Cryst. E64, o2322–o2323.  Web of Science CSD CrossRef CAS IUCr Journals 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 citationStoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.  Google Scholar
 First citationVega-Noverola, A. P., Soto, J. M., Noguera, F. P., Mauri, J. M. & Spickett, G. W. R. (1989). US Patent No. 4 877 780.  Google Scholar
 First citationYoo, C. L., Fettinger, J. C. & Kurth, M. J. (2005). J. Org. Chem. 70, 6941–6943.  Web of Science CSD CrossRef PubMed CAS 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 65| Part 6| June 2009| Page o1334
doi:10.1107/S1600536809018236
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