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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1342.
Published online 2008 June 25. doi:  10.1107/S1600536808018679
PMCID: PMC2961795

2-Chloro-N-(2,3-dichloro­phen­yl)benzamide

Abstract

Two independent mol­ecules comprise the asymmetric unit in the title compound, C13H8Cl3NO, each with the amide N—H and C=O bonds trans to each other. The mol­ecules are linked into chains through inter­molecular N—H(...)O and N—H(...)Cl hydrogen bonds.

Related literature

For related literature, see: Gowda et al. (2003 [triangle], 2007 [triangle], 2008 [triangle]).

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Object name is e-64-o1342-scheme1.jpg

Experimental

Crystal data

  • C13H8Cl3NO
  • M r = 300.55
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1342-efi1.jpg
  • a = 12.310 (1) Å
  • b = 7.8307 (6) Å
  • c = 14.407 (2) Å
  • β = 111.52 (1)°
  • V = 1292.0 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.69 mm−1
  • T = 299 (2) K
  • 0.75 × 0.75 × 0.18 mm

Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 [triangle]) T min = 0.624, T max = 0.885
  • 5882 measured reflections
  • 3936 independent reflections
  • 3430 reflections with I > 2σ(I)
  • R int = 0.014

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.104
  • S = 1.14
  • 3936 reflections
  • 326 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.28 e Å−3
  • Absolute structure: (Flack, 1983 [triangle]), 365 Friedel pairs
  • Flack parameter: 0.12 (5)

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97 .

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018679/tk2277sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018679/tk2277Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

supplementary crystallographic information

Comment

In the present work, the structure of 2-chloro-N-(2,3-dichlorophenyl)- benzamide (I, N23DCP2CBA) has been determined to explore the effect of substituents on the structures of benzanilides (Gowda et al., 2003; 2007; 2008). The amide N—H and C=O bonds in each of the two molecules comprising the crystallographic asymmetric unit are trans to each other (Fig. 1), similar to that observed in 2-chloro-N-(phenyl)-benzamide (NP2CBA) (Gowda et al., 2003), 2-chloro-N-(2-chlorophenyl)-benzamide (N2CP2CBA) (Gowda et al., 2007), and 2-chloro-N-(3-chlorophenyl)-benzamide (N3CP2CBA) (Gowda et al., 2008). In one of the molecules, the conformation of the N—H bond is syn to both the ortho and meta-chloro groups in the aniline ring and of the C=O bond group is also syn to the ortho-chloro group in the benzoyl ring. By contrast, the conformations of these bonds in the second independent molecule are intermediate between syn and anti to the respective groups. The above conformations are in contrast to the syn conformations of both the amide N—H and C=O bonds, with respect to the ortho-chloro groups in the benzoyl and aniline rings, respectively, observed in N2CP2CBA (Gowda et al., 2007). Further, in N3CP2CBA, the conformation of the C=O bond is syn to the ortho-chloro group of the benzoyl ring, while the N—H bond is anti to the meta-chloro group of the aniline ring (Gowda et al., 2008). The –NHCO– group makes the dihedral angles of 42.24 (14)° (molecule 1), 48.89 (12)° (molecule 2), and 35.31 (19)° (molecule 1), 41.88 (13)° (molecule 2) with the benzoyl and aniline rings, respectively. The benzoyl and aniline rings form the dihedral angles of 12.30 (10)° (molecule 1) and 7.25 (9)°) (molecule 2). In the crystal structure of (I), the molecules are linked by intermolecular N—H···O and N—H···Cl hydrogen bonds (Table 1) forming chains running along the a axis, as shown in Fig. 2.

Experimental

Compound (I) was prepared according to the literature method (Gowda et al., 2003). The purity of the compound was confirmed by melting point, and IR and NMR spectra. Single crystals were obtained from an ethanolic solution of (I)

Refinement

The H atoms were positioned with idealized geometry using a riding model with C—H = 0.93 Å and N—H = 0.86 Å, and with Uiso(H) = 1.2Ueq(N, C).

Figures

Fig. 1.
Molecular structure of (I) showing the atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Molecular packing of (I) with hydrogen bonding shown as dashed lines.

Crystal data

C13H8Cl3NOF000 = 608
Mr = 300.55Dx = 1.545 Mg m3
Monoclinic, PcMo Kα radiation λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 3409 reflections
a = 12.310 (1) Åθ = 2.6–27.5º
b = 7.8307 (6) ŵ = 0.69 mm1
c = 14.407 (2) ÅT = 299 (2) K
β = 111.52 (1)ºThick plate, colourless
V = 1292.0 (2) Å30.75 × 0.75 × 0.18 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector3936 independent reflections
Radiation source: fine-focus sealed tube3430 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.014
T = 299(2) Kθmax = 26.4º
Rotation method data acquisition using ω and [var phi] scansθmin = 2.6º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)h = −15→13
Tmin = 0.624, Tmax = 0.885k = −9→9
5882 measured reflectionsl = −15→18

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.032  w = 1/[σ2(Fo2) + (0.0715P)2 + 0.0104P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.104(Δ/σ)max = 0.003
S = 1.14Δρmax = 0.29 e Å3
3936 reflectionsΔρmin = −0.28 e Å3
326 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.0118 (14)
Primary atom site location: structure-invariant direct methodsAbsolute structure: (Flack, 1983), 365 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.12 (5)

Special details

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)

xyzUiso*/Ueq
Cl10.80355 (8)−0.16289 (10)0.22458 (7)0.0542 (2)
Cl20.53668 (10)−0.25096 (14)0.12596 (9)0.0739 (3)
Cl31.08381 (10)0.01157 (12)0.38808 (9)0.0745 (3)
O10.8488 (2)0.4258 (3)0.36026 (18)0.0537 (6)
N10.8566 (2)0.2051 (3)0.26179 (19)0.0411 (6)
H1N0.90280.14260.24370.049*
C10.7362 (3)0.1682 (4)0.2183 (2)0.0359 (6)
C20.7006 (3)−0.0018 (4)0.1965 (2)0.0420 (7)
C30.5819 (3)−0.0414 (5)0.1521 (3)0.0493 (8)
C40.4996 (3)0.0858 (5)0.1303 (3)0.0566 (9)
H40.42060.05890.10180.068*
C50.5342 (4)0.2543 (5)0.1510 (3)0.0597 (10)
H50.47830.34030.13570.072*
C60.6515 (3)0.2954 (5)0.1941 (3)0.0498 (8)
H60.67380.40910.20710.060*
C70.9063 (3)0.3294 (4)0.3292 (2)0.0388 (7)
C81.0362 (3)0.3540 (4)0.3601 (2)0.0379 (7)
C91.1208 (3)0.2248 (5)0.3829 (3)0.0478 (8)
C101.2384 (4)0.2639 (6)0.4080 (3)0.0613 (10)
H101.29360.17690.42260.074*
C111.2727 (3)0.4310 (6)0.4112 (3)0.0629 (10)
H111.35130.45690.42760.076*
C121.1924 (4)0.5604 (5)0.3904 (3)0.0576 (9)
H121.21640.67350.39310.069*
C131.0746 (3)0.5220 (4)0.3654 (3)0.0455 (7)
H131.02060.61040.35190.055*
Cl40.61868 (9)0.43793 (11)−0.06792 (10)0.0700 (3)
Cl50.41892 (8)0.16238 (16)−0.14120 (9)0.0747 (3)
Cl61.22481 (9)0.23655 (14)0.13296 (10)0.0727 (3)
O20.9822 (2)0.1549 (3)0.13253 (16)0.0436 (5)
N20.8590 (2)0.2974 (3)−0.00345 (19)0.0400 (6)
H2N0.85030.3882−0.03900.048*
C140.7697 (3)0.1737 (4)−0.0342 (2)0.0351 (6)
C150.6526 (3)0.2227 (4)−0.0670 (2)0.0412 (7)
C160.5648 (3)0.1028 (4)−0.0983 (2)0.0422 (7)
C170.5907 (3)−0.0713 (5)−0.0947 (3)0.0485 (8)
H170.5314−0.1525−0.11330.058*
C180.7064 (3)−0.1199 (4)−0.0630 (3)0.0471 (8)
H180.7250−0.2351−0.06180.056*
C190.7949 (3)−0.0002 (4)−0.0329 (2)0.0413 (7)
H190.8723−0.0359−0.01150.050*
C200.9589 (3)0.2819 (4)0.0796 (2)0.0347 (6)
C211.0337 (3)0.4382 (4)0.1036 (2)0.0364 (6)
C221.1550 (3)0.4300 (4)0.1294 (2)0.0432 (7)
C231.2224 (3)0.5764 (6)0.1521 (3)0.0598 (9)
H231.30260.56970.16800.072*
C241.1699 (4)0.7327 (5)0.1510 (3)0.0635 (11)
H241.21490.83160.16560.076*
C251.0513 (4)0.7428 (5)0.1285 (3)0.0604 (10)
H251.01680.84790.12970.072*
C260.9839 (3)0.5976 (4)0.1043 (2)0.0464 (8)
H260.90370.60600.08820.056*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0515 (5)0.0378 (4)0.0674 (5)0.0092 (4)0.0148 (4)−0.0055 (4)
Cl20.0619 (7)0.0521 (5)0.0969 (8)−0.0162 (5)0.0164 (6)−0.0149 (5)
Cl30.0614 (6)0.0395 (5)0.1037 (8)0.0091 (5)0.0080 (6)0.0133 (5)
O10.0443 (14)0.0479 (13)0.0663 (14)0.0016 (11)0.0173 (11)−0.0199 (12)
N10.0360 (14)0.0392 (13)0.0486 (14)0.0038 (11)0.0162 (11)−0.0078 (11)
C10.0353 (15)0.0343 (15)0.0375 (15)0.0061 (12)0.0127 (12)−0.0007 (12)
C20.0448 (17)0.0418 (17)0.0389 (16)0.0093 (15)0.0149 (13)−0.0026 (13)
C30.0467 (19)0.0471 (18)0.0511 (19)−0.0055 (16)0.0147 (15)−0.0106 (15)
C40.0379 (19)0.060 (2)0.064 (2)−0.0022 (17)0.0095 (15)−0.0069 (18)
C50.043 (2)0.053 (2)0.074 (3)0.0176 (17)0.0104 (17)−0.0041 (18)
C60.050 (2)0.0376 (17)0.055 (2)0.0071 (15)0.0115 (15)−0.0063 (15)
C70.0414 (17)0.0326 (15)0.0438 (16)0.0041 (13)0.0172 (13)0.0011 (13)
C80.0400 (17)0.0393 (16)0.0336 (14)0.0029 (13)0.0128 (12)0.0023 (12)
C90.0426 (19)0.0434 (18)0.0506 (18)0.0012 (15)0.0090 (14)0.0056 (14)
C100.044 (2)0.068 (2)0.064 (2)0.0131 (18)0.0096 (16)0.0015 (19)
C110.042 (2)0.073 (3)0.071 (2)−0.007 (2)0.0159 (17)0.003 (2)
C120.054 (2)0.055 (2)0.065 (2)−0.0116 (18)0.0231 (17)0.0018 (18)
C130.0457 (19)0.0384 (16)0.0527 (19)−0.0038 (15)0.0185 (15)0.0002 (14)
Cl40.0492 (5)0.0352 (4)0.1229 (9)0.0110 (4)0.0283 (5)0.0141 (5)
Cl50.0330 (4)0.0743 (7)0.1059 (8)0.0019 (5)0.0126 (4)0.0079 (6)
Cl60.0455 (5)0.0593 (6)0.1157 (9)0.0121 (5)0.0322 (5)−0.0116 (6)
O20.0459 (13)0.0357 (11)0.0453 (11)0.0033 (10)0.0119 (9)0.0058 (9)
N20.0359 (14)0.0321 (12)0.0449 (14)0.0007 (11)0.0065 (11)0.0086 (10)
C140.0328 (15)0.0351 (15)0.0367 (14)−0.0006 (12)0.0119 (11)0.0055 (12)
C150.0423 (18)0.0341 (16)0.0485 (17)0.0067 (14)0.0184 (14)0.0075 (13)
C160.0329 (16)0.0432 (17)0.0510 (18)−0.0021 (13)0.0161 (14)0.0028 (14)
C170.047 (2)0.0457 (18)0.0525 (19)−0.0114 (16)0.0185 (15)−0.0047 (15)
C180.054 (2)0.0301 (15)0.0572 (19)0.0024 (14)0.0201 (16)−0.0038 (14)
C190.0352 (16)0.0394 (16)0.0454 (17)0.0053 (14)0.0101 (13)0.0010 (13)
C200.0359 (16)0.0339 (14)0.0383 (15)0.0072 (13)0.0184 (12)0.0006 (12)
C210.0363 (16)0.0335 (15)0.0374 (15)0.0019 (13)0.0111 (12)−0.0031 (12)
C220.0395 (18)0.0407 (17)0.0472 (17)0.0038 (14)0.0133 (13)−0.0028 (14)
C230.043 (2)0.067 (2)0.060 (2)−0.0104 (19)0.0078 (16)−0.0007 (19)
C240.077 (3)0.0399 (19)0.054 (2)−0.0137 (19)−0.0003 (19)0.0006 (15)
C250.074 (3)0.0357 (17)0.0509 (19)0.0061 (18)−0.0013 (17)−0.0010 (14)
C260.0487 (19)0.0397 (16)0.0413 (17)0.0060 (15)0.0052 (14)0.0001 (14)

Geometric parameters (Å, °)

Cl1—C21.728 (3)Cl4—C151.735 (3)
Cl2—C31.730 (4)Cl5—C161.735 (3)
Cl3—C91.739 (4)Cl6—C221.733 (3)
O1—C71.226 (4)O2—C201.222 (4)
N1—C71.353 (4)N2—C201.371 (4)
N1—C11.411 (4)N2—C141.409 (4)
N1—H1N0.8600N2—H2N0.8600
C1—C61.391 (5)C14—C191.395 (4)
C1—C21.401 (4)C14—C151.396 (4)
C2—C31.397 (5)C15—C161.377 (5)
C3—C41.373 (5)C16—C171.397 (5)
C4—C51.384 (6)C17—C181.380 (5)
C4—H40.9300C17—H170.9300
C5—C61.384 (6)C18—C191.381 (5)
C5—H50.9300C18—H180.9300
C6—H60.9300C19—H190.9300
C7—C81.507 (5)C20—C211.493 (4)
C8—C131.390 (5)C21—C261.393 (4)
C8—C91.402 (5)C21—C221.402 (4)
C9—C101.392 (6)C22—C231.382 (5)
C10—C111.371 (6)C23—C241.382 (6)
C10—H100.9300C23—H230.9300
C11—C121.370 (6)C24—C251.376 (7)
C11—H110.9300C24—H240.9300
C12—C131.392 (5)C25—C261.375 (5)
C12—H120.9300C25—H250.9300
C13—H130.9300C26—H260.9300
C7—N1—C1126.2 (3)C20—N2—C14124.1 (3)
C7—N1—H1N116.9C20—N2—H2N118.0
C1—N1—H1N116.9C14—N2—H2N118.0
C6—C1—C2118.7 (3)C19—C14—C15118.0 (3)
C6—C1—N1122.2 (3)C19—C14—N2121.5 (3)
C2—C1—N1119.1 (3)C15—C14—N2120.5 (3)
C3—C2—C1120.2 (3)C16—C15—C14120.8 (3)
C3—C2—Cl1119.9 (3)C16—C15—Cl4120.1 (3)
C1—C2—Cl1119.9 (3)C14—C15—Cl4119.0 (3)
C4—C3—C2120.3 (3)C15—C16—C17120.8 (3)
C4—C3—Cl2119.1 (3)C15—C16—Cl5121.3 (3)
C2—C3—Cl2120.6 (3)C17—C16—Cl5117.9 (3)
C3—C4—C5119.9 (3)C18—C17—C16118.4 (3)
C3—C4—H4120.0C18—C17—H17120.8
C5—C4—H4120.0C16—C17—H17120.8
C6—C5—C4120.4 (4)C17—C18—C19121.1 (3)
C6—C5—H5119.8C17—C18—H18119.4
C4—C5—H5119.8C19—C18—H18119.4
C5—C6—C1120.6 (4)C18—C19—C14120.8 (3)
C5—C6—H6119.7C18—C19—H19119.6
C1—C6—H6119.7C14—C19—H19119.6
O1—C7—N1122.3 (3)O2—C20—N2123.1 (3)
O1—C7—C8120.4 (3)O2—C20—C21122.6 (3)
N1—C7—C8117.1 (3)N2—C20—C21114.2 (2)
C13—C8—C9117.5 (3)C26—C21—C22117.9 (3)
C13—C8—C7116.1 (3)C26—C21—C20120.0 (3)
C9—C8—C7126.4 (3)C22—C21—C20122.0 (3)
C10—C9—C8121.0 (3)C23—C22—C21120.9 (3)
C10—C9—Cl3117.6 (3)C23—C22—Cl6118.0 (3)
C8—C9—Cl3121.3 (3)C21—C22—Cl6121.1 (3)
C11—C10—C9119.8 (4)C22—C23—C24119.7 (4)
C11—C10—H10120.1C22—C23—H23120.2
C9—C10—H10120.1C24—C23—H23120.2
C12—C11—C10120.7 (4)C25—C24—C23120.3 (4)
C12—C11—H11119.6C25—C24—H24119.9
C10—C11—H11119.6C23—C24—H24119.9
C11—C12—C13119.7 (4)C26—C25—C24120.1 (4)
C11—C12—H12120.1C26—C25—H25119.9
C13—C12—H12120.1C24—C25—H25119.9
C8—C13—C12121.3 (3)C25—C26—C21121.1 (3)
C8—C13—H13119.4C25—C26—H26119.5
C12—C13—H13119.4C21—C26—H26119.5
C7—N1—C1—C636.2 (5)C20—N2—C14—C19−43.2 (4)
C7—N1—C1—C2−145.3 (3)C20—N2—C14—C15136.7 (3)
C6—C1—C2—C3−0.5 (5)C19—C14—C15—C16−0.8 (4)
N1—C1—C2—C3−179.1 (3)N2—C14—C15—C16179.2 (3)
C6—C1—C2—Cl1179.5 (3)C19—C14—C15—Cl4179.2 (2)
N1—C1—C2—Cl10.8 (4)N2—C14—C15—Cl4−0.7 (4)
C1—C2—C3—C4−0.6 (5)C14—C15—C16—C172.3 (5)
Cl1—C2—C3—C4179.5 (3)Cl4—C15—C16—C17−177.8 (3)
C1—C2—C3—Cl2−179.4 (3)C14—C15—C16—Cl5−178.9 (2)
Cl1—C2—C3—Cl20.7 (4)Cl4—C15—C16—Cl51.1 (4)
C2—C3—C4—C51.0 (6)C15—C16—C17—C18−2.6 (5)
Cl2—C3—C4—C5179.9 (3)Cl5—C16—C17—C18178.5 (3)
C3—C4—C5—C6−0.5 (6)C16—C17—C18—C191.6 (5)
C4—C5—C6—C1−0.6 (6)C17—C18—C19—C14−0.3 (5)
C2—C1—C6—C51.0 (5)C15—C14—C19—C18−0.1 (5)
N1—C1—C6—C5179.6 (3)N2—C14—C19—C18179.8 (3)
C1—N1—C7—O10.1 (5)C14—N2—C20—O23.4 (5)
C1—N1—C7—C8−175.7 (3)C14—N2—C20—C21−173.0 (3)
O1—C7—C8—C13−39.9 (4)O2—C20—C21—C26−128.9 (3)
N1—C7—C8—C13135.9 (3)N2—C20—C21—C2647.5 (4)
O1—C7—C8—C9140.8 (3)O2—C20—C21—C2248.7 (4)
N1—C7—C8—C9−43.4 (4)N2—C20—C21—C22−134.9 (3)
C13—C8—C9—C10−1.1 (5)C26—C21—C22—C23−1.8 (5)
C7—C8—C9—C10178.2 (3)C20—C21—C22—C23−179.4 (3)
C13—C8—C9—Cl3175.0 (2)C26—C21—C22—Cl6178.6 (2)
C7—C8—C9—Cl3−5.7 (5)C20—C21—C22—Cl61.0 (4)
C8—C9—C10—C110.3 (6)C21—C22—C23—C241.1 (5)
Cl3—C9—C10—C11−175.8 (3)Cl6—C22—C23—C24−179.3 (3)
C9—C10—C11—C120.4 (6)C22—C23—C24—C250.6 (6)
C10—C11—C12—C13−0.3 (6)C23—C24—C25—C26−1.7 (6)
C9—C8—C13—C121.2 (5)C24—C25—C26—C211.0 (6)
C7—C8—C13—C12−178.2 (3)C22—C21—C26—C250.7 (5)
C11—C12—C13—C8−0.5 (6)C20—C21—C26—C25178.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O20.862.162.850 (3)137
N1—H1N···Cl30.862.643.114 (3)116
N2—H2N···O1i0.862.052.896 (3)167

Symmetry codes: (i) x, −y+1, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2277).

References

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  • Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o1300. [PMC free article] [PubMed]
  • Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230.
  • Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
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