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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 1| January 2008| Page o60
https://doi.org/10.1107/S1600536807062010

(2E)-1-(4-Methyl­phen­yl)-3-(2,3,5-tri­chloro­phen­yl)prop-2-en-1-one

A. Thiruvalluvar,a* M. Subramanyam,a R. J. Butcher,b Prakash Karegoudarc and B. Shivarama Hollad

aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamil Nadu, India, bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, cSeQuent Scientific Limited, 120 A&B Baikampady Industrial Area, New Mangalore, India, and dDepartment of Chemistry, Mangalore University, Karnataka 574 199, India
*Correspondence e-mail: athiru@vsnl.net

(Received 17 November 2007; accepted 22 November 2007; online 6 December 2007)

In the title mol­ecule, C16H11Cl3O, the dihedral angle between the two benzene rings is 33.2 (1)°. The crystal packing is stabilized by C—H⋯O hydrogen bonds.

Related literature

For the uses of chalcones, see: John et al. (2007[John, A., Mithun, A., Holla, B. S., Shashikala, H. D., Umesh, G. & Chandrasekharan, K. (2007). Opt. Commun. 296, 235-241.]). For related crystal structures, see: Thiruvalluvar et al. (2007a[Thiruvalluvar, A., Subramanyam, M., Butcher, R. J., Adhikari, A. V. & Wagle, S. (2007a). Acta Cryst. E63, o4536.],b[Thiruvalluvar, A., Subramanyam, M., Butcher, R. J., Adhikari, A. V. & Karabasanagouda, T. (2007b). Acta Cryst. E63, o4716.]).

[Scheme 1]

Experimental

Crystal data

  • C16H11Cl3O

  • Mr = 325.60

  • Orthorhombic, P b c a

  • a = 7.6432 (4) Å

  • b = 10.5118 (4) Å

  • c = 36.2356 (12) Å

  • V = 2911.3 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.62 mm−1

  • T = 200 (2) K

  • 0.34 × 0.27 × 0.22 mm
Data collection

  • Oxford Diffraction Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]) Tmin = 0.818, Tmax = 0.877

  • 38087 measured reflections

  • 5035 independent reflections

  • 2561 reflections with I > 2σ(I)

  • Rint = 0.069
Refinement

  • R[F2 > 2σ(F2)] = 0.064

  • wR(F2) = 0.168

  • S = 1.03

  • 5035 reflections

  • 181 parameters

  • H-atom parameters not refined

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.39 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C13—H13⋯Oi 0.95 2.43 3.372 (3) 169
Symmetry code: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z].

Data collection: CrysAlis CCD (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990[Sheldrick, G. M. (1990). Acta Cryst. A46, 467-473.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Version 2.1. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807062010/lx2037sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062010/lx2037Isup2.hkl

checkCIF report


Comment top

Chalcones and their derivatives show some interesting physical properties like liquid crystalline nature and nonlinear optical effect(John et al., 2007). Thiruvalluvar et al. (2007a,b) have reported related crystal structures of chalcones. As a continuation of our work on chalcones, we report here the x-ray crystal structure of the title molecule, C16H11Cl3O, Fig.1.

The dihedral angle between the methylphenyl ring and the trichlorophenyl ring is 33.2 (1)°. The crystal packing is stabilized by C13—H13···Oi hydrogen bonds (Table 1 & Fig. 2; symmetry code as in Fig. 2)

Related literature top

For the uses of chalcones, see: John et al. (2007). For related crystal structures, see: Thiruvalluvar et al. (2007a,b).

Experimental top

To the mixture of 2,3,5-trichlorobenzaldehyde (21 g, 0.1 mol) and 4-methylacetophenone (14.7 g, 0.11 mol) in methanol (100 ml), 20% of sodium hydroxide (8 g, 0.2 mol) was added at 288–293 K, after stirring for 8 h at 303 K. Solid obtained was filtered, washed with water and dried. The product was recrystallized using ethyl acetate. Yield was 27.6 g(85%).

Refinement top

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93–0.96Å and Uiso = 1.2–1.5 times Ueq(C).

Structure description top

Chalcones and their derivatives show some interesting physical properties like liquid crystalline nature and nonlinear optical effect(John et al., 2007). Thiruvalluvar et al. (2007a,b) have reported related crystal structures of chalcones. As a continuation of our work on chalcones, we report here the x-ray crystal structure of the title molecule, C16H11Cl3O, Fig.1.

The dihedral angle between the methylphenyl ring and the trichlorophenyl ring is 33.2 (1)°. The crystal packing is stabilized by C13—H13···Oi hydrogen bonds (Table 1 & Fig. 2; symmetry code as in Fig. 2)

For the uses of chalcones, see: John et al. (2007). For related crystal structures, see: Thiruvalluvar et al. (2007a,b).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atomic numbering and 50% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radius.
[Figure 2] Fig. 2. The packing of the title compound, viewed down the a axis. Dashed lines indicate hydrogen bonds. [Symmetry code: (i) -x + 1/2, y - 1/2, z.]
(2E)-1-(4-Methylphenyl)-3-(2,3,5-trichlorophenyl)prop-2-en-1-one top
Crystal data top
C16H11Cl3ODx = 1.486 Mg m−3
Mr = 325.60Melting point: 467(1) K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 8272 reflections
a = 7.6432 (4) Åθ = 4.7–32.4°
b = 10.5118 (4) ŵ = 0.62 mm−1
c = 36.2356 (12) ÅT = 200 K
V = 2911.3 (2) Å3Prism, colourless
Z = 80.34 × 0.27 × 0.22 mm
F(000) = 1328
Data collection top
Oxford Diffraction Gemini
diffractometer		5035 independent reflections
Radiation source: fine-focus sealed tube2561 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
Detector resolution: 10.5081 pixels mm-1θmax = 32.5°, θmin = 4.7°
φ and ω scansh = −11→10
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		k = −15→15
Tmin = 0.818, Tmax = 0.877l = −54→51
38087 measured reflections
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H-atom parameters not refined
S = 1.03 w = 1/[σ2(Fo2) + (0.0546P)2 + 3.6539P]
where P = (Fo2 + 2Fc2)/3
5035 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.32 e Å−3
0 restraintsΔρmin = −0.39 e Å−3
Crystal data top
C16H11Cl3OV = 2911.3 (2) Å3
Mr = 325.60Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 7.6432 (4) ŵ = 0.62 mm−1
b = 10.5118 (4) ÅT = 200 K
c = 36.2356 (12) Å0.34 × 0.27 × 0.22 mm
Data collection top
Oxford Diffraction Gemini
diffractometer		5035 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		2561 reflections with I > 2σ(I)
Tmin = 0.818, Tmax = 0.877Rint = 0.069
38087 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0640 restraints
wR(F2) = 0.168H-atom parameters not refined
S = 1.03Δρmax = 0.32 e Å−3
5035 reflectionsΔρmin = −0.39 e Å−3
181 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Cl10.04881 (12)0.50228 (8)0.19318 (2)0.0482 (3)
Cl2−0.10841 (14)0.32270 (9)0.25375 (2)0.0598 (3)
Cl3−0.06450 (13)−0.07474 (8)0.16142 (2)0.0501 (3)
O0.2908 (3)0.52884 (19)0.06638 (5)0.0419 (7)
C10.1438 (4)0.3651 (3)−0.05988 (7)0.0315 (8)
C20.2542 (4)0.4610 (3)−0.04685 (8)0.0358 (9)
C30.2707 (4)0.4818 (3)−0.00924 (7)0.0357 (9)
C40.1813 (3)0.4086 (2)0.01640 (7)0.0265 (7)
C50.0720 (4)0.3127 (3)0.00328 (7)0.0320 (8)
C60.0552 (4)0.2926 (3)−0.03434 (7)0.0341 (8)
C70.1220 (4)0.3410 (3)−0.10050 (8)0.0448 (10)
C80.0644 (3)0.2917 (3)0.14942 (7)0.0294 (8)
C90.0205 (4)0.3419 (3)0.18411 (7)0.0326 (8)
C10−0.0503 (4)0.2623 (3)0.21107 (7)0.0380 (9)
C11−0.0769 (4)0.1338 (3)0.20478 (8)0.0392 (9)
C12−0.0301 (4)0.0868 (3)0.17038 (7)0.0366 (9)
C130.0398 (4)0.1617 (3)0.14318 (7)0.0328 (8)
C140.2066 (4)0.4357 (3)0.05641 (7)0.0299 (8)
C150.1296 (4)0.3471 (3)0.08389 (7)0.0350 (9)
C160.1330 (4)0.3734 (3)0.11973 (7)0.0321 (8)
H20.318060.51195−0.063790.0429*
H30.345250.54801−0.000810.0428*
H50.008850.260930.020160.0385*
H6−0.019960.22678−0.042800.0409*
H7A0.196200.26939−0.107910.0671*
H7B0.156160.41717−0.114330.0671*
H7C−0.000660.32072−0.105760.0671*
H11−0.125250.080110.223230.0470*
H130.071600.125300.120130.0393*
H150.076940.270260.075690.0420*
H160.184380.451940.126860.0385*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0641 (6)0.0425 (4)0.0379 (4)0.0013 (4)0.0016 (4)−0.0104 (3)
Cl20.0763 (7)0.0702 (6)0.0328 (4)−0.0083 (5)0.0172 (4)−0.0141 (4)
Cl30.0708 (6)0.0372 (4)0.0422 (4)−0.0073 (4)0.0041 (4)0.0009 (3)
O0.0503 (14)0.0385 (12)0.0370 (10)−0.0092 (10)−0.0045 (10)−0.0030 (9)
C10.0329 (15)0.0324 (14)0.0292 (13)0.0067 (12)0.0021 (11)−0.0019 (11)
C20.0360 (16)0.0353 (15)0.0361 (14)−0.0053 (13)0.0051 (13)0.0031 (12)
C30.0342 (16)0.0341 (15)0.0387 (15)−0.0083 (13)−0.0009 (13)0.0007 (12)
C40.0259 (13)0.0239 (13)0.0296 (12)0.0032 (11)−0.0010 (11)0.0021 (10)
C50.0340 (15)0.0293 (14)0.0328 (13)−0.0049 (12)0.0030 (12)0.0046 (11)
C60.0349 (16)0.0326 (14)0.0347 (14)−0.0054 (13)−0.0023 (12)−0.0026 (11)
C70.0472 (19)0.057 (2)0.0302 (14)0.0024 (17)0.0017 (14)−0.0040 (14)
C80.0274 (14)0.0352 (14)0.0255 (12)0.0041 (12)−0.0020 (11)−0.0007 (10)
C90.0338 (15)0.0332 (14)0.0309 (13)0.0025 (12)−0.0027 (12)−0.0054 (11)
C100.0411 (17)0.0489 (18)0.0241 (12)−0.0014 (15)0.0030 (12)−0.0066 (12)
C110.0407 (17)0.0488 (18)0.0280 (14)−0.0054 (15)0.0003 (12)0.0007 (12)
C120.0435 (18)0.0376 (16)0.0286 (13)−0.0007 (14)−0.0025 (12)−0.0012 (11)
C130.0360 (15)0.0373 (15)0.0250 (12)0.0038 (13)−0.0008 (12)−0.0007 (11)
C140.0287 (14)0.0282 (14)0.0329 (13)0.0030 (12)−0.0029 (11)−0.0006 (11)
C150.0437 (17)0.0291 (14)0.0323 (14)−0.0019 (13)−0.0021 (13)−0.0014 (11)
C160.0333 (15)0.0316 (14)0.0314 (14)0.0022 (12)−0.0006 (12)−0.0022 (11)
Geometric parameters (Å, º) top
Cl1—C91.731 (3)C10—C111.385 (4)
Cl2—C101.730 (3)C11—C121.388 (4)
Cl3—C121.749 (3)C12—C131.370 (4)
O—C141.226 (4)C14—C151.485 (4)
C1—C21.397 (4)C15—C161.328 (4)
C1—C61.377 (4)C2—H20.9500
C1—C71.503 (4)C3—H30.9500
C2—C31.386 (4)C5—H50.9500
C3—C41.386 (4)C6—H60.9500
C4—C51.393 (4)C7—H7A0.9800
C4—C141.490 (4)C7—H7B0.9800
C5—C61.385 (4)C7—H7C0.9800
C8—C91.404 (4)C11—H110.9500
C8—C131.398 (4)C13—H130.9500
C8—C161.473 (4)C15—H150.9500
C9—C101.396 (4)C16—H160.9500
Cl1···Cl23.1344 (12)C6···H3x2.9400
Cl2···C9i3.627 (3)C13···H7Axi3.0100
Cl2···Cl13.1344 (12)C13···H152.7100
Cl2···Cl3ii3.5154 (11)C14···H6viii2.7400
Cl3···Cl2iii3.5154 (11)C15···H52.6500
Cl3···C7iv3.592 (3)C15···H132.7100
Cl1···H162.6700H2···H7B2.4200
Cl3···H7Aiv2.9900H3···O2.4800
O···C13v3.372 (3)H3···C3vii2.9700
O···H32.4800H3···H3vii2.5700
O···H162.4700H3···C5v2.8600
O···H13v2.4300H3···C6v2.9400
O···H15v2.7500H5···C152.6500
C1···C14vi3.402 (4)H5···H152.0800
C3···C3vii3.589 (4)H6···H7C2.4900
C3···C5vi3.402 (4)H6···C4xi2.8600
C4···C5vi3.583 (4)H6···C14xi2.7400
C4···C4vi3.576 (3)H7A···C13viii3.0100
C5···C4vi3.583 (4)H7A···Cl3iv2.9900
C5···C3vi3.402 (4)H7B···H22.4200
C6···C14vi3.578 (4)H7C···H62.4900
C7···Cl3iv3.592 (3)H13···C152.7100
C7···C13viii3.548 (4)H13···H152.2200
C9···Cl2ix3.627 (3)H13···Ox2.4300
C13···Ox3.372 (3)H15···C52.6600
C13···C7xi3.548 (4)H15···C132.7100
C14···C6vi3.578 (4)H15···H52.0800
C14···C1vi3.402 (4)H15···H132.2200
C3···H3vii2.9700H15···Ox2.7500
C4···H6viii2.8600H16···Cl12.6700
C5···H152.6600H16···O2.4700
C5···H3x2.8600
C2—C1—C6118.0 (2)C4—C14—C15118.8 (2)
C2—C1—C7121.3 (3)C14—C15—C16121.2 (3)
C6—C1—C7120.7 (3)C8—C16—C15125.9 (3)
C1—C2—C3120.1 (3)C1—C2—H2120.00
C2—C3—C4121.8 (3)C3—C2—H2120.00
C3—C4—C5117.9 (2)C2—C3—H3119.00
C3—C4—C14118.8 (2)C4—C3—H3119.00
C5—C4—C14123.3 (2)C4—C5—H5120.00
C4—C5—C6120.1 (3)C6—C5—H5120.00
C1—C6—C5122.1 (3)C1—C6—H6119.00
C9—C8—C13118.7 (3)C5—C6—H6119.00
C9—C8—C16121.3 (3)C1—C7—H7A109.00
C13—C8—C16120.0 (2)C1—C7—H7B109.00
Cl1—C9—C8120.4 (2)C1—C7—H7C109.00
Cl1—C9—C10120.0 (2)H7A—C7—H7B109.00
C8—C9—C10119.6 (3)H7A—C7—H7C109.00
Cl2—C10—C9120.4 (2)H7B—C7—H7C109.00
Cl2—C10—C11117.9 (2)C10—C11—H11121.00
C9—C10—C11121.8 (3)C12—C11—H11121.00
C10—C11—C12117.2 (3)C8—C13—H13120.00
Cl3—C12—C11118.3 (2)C12—C13—H13120.00
Cl3—C12—C13118.9 (2)C14—C15—H15119.00
C11—C12—C13122.8 (3)C16—C15—H15119.00
C8—C13—C12119.9 (3)C8—C16—H16117.00
O—C14—C4120.5 (2)C15—C16—H16117.00
O—C14—C15120.8 (2)
C6—C1—C2—C3−0.7 (5)C9—C8—C13—C121.6 (4)
C7—C1—C2—C3179.5 (3)C16—C8—C13—C12−177.6 (3)
C2—C1—C6—C50.4 (5)C9—C8—C16—C15−158.6 (3)
C7—C1—C6—C5−179.8 (3)C13—C8—C16—C1520.6 (4)
C1—C2—C3—C40.7 (5)Cl1—C9—C10—Cl2−0.6 (4)
C2—C3—C4—C5−0.4 (4)Cl1—C9—C10—C11179.3 (2)
C2—C3—C4—C14179.5 (3)C8—C9—C10—Cl2−179.0 (2)
C3—C4—C5—C60.1 (4)C8—C9—C10—C110.8 (5)
C14—C4—C5—C6−179.8 (3)Cl2—C10—C11—C12179.8 (2)
C3—C4—C14—O7.2 (4)C9—C10—C11—C120.0 (5)
C3—C4—C14—C15−172.1 (3)C10—C11—C12—Cl3−179.3 (2)
C5—C4—C14—O−172.9 (3)C10—C11—C12—C130.0 (5)
C5—C4—C14—C157.8 (4)Cl3—C12—C13—C8178.4 (2)
C4—C5—C6—C1−0.1 (5)C11—C12—C13—C8−0.9 (5)
C13—C8—C9—Cl1179.9 (2)O—C14—C15—C167.5 (5)
C13—C8—C9—C10−1.6 (4)C4—C14—C15—C16−173.2 (3)
C16—C8—C9—Cl1−0.9 (4)C14—C15—C16—C8−178.6 (3)
C16—C8—C9—C10177.6 (3)
Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x, −y, −z; (v) −x+1/2, y+1/2, z; (vi) −x, −y+1, −z; (vii) −x+1, −y+1, −z; (viii) x+1/2, −y+1/2, −z; (ix) x+1/2, y, −z+1/2; (x) −x+1/2, y−1/2, z; (xi) x−1/2, −y+1/2, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···Ox0.952.433.372 (3)169
Symmetry code: (x) −x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formulaC16H11Cl3O
Mr325.60
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)200
a, b, c (Å)7.6432 (4), 10.5118 (4), 36.2356 (12)
V (Å3)2911.3 (2)
Z8
Radiation typeMo Kα
µ (mm−1)0.62
Crystal size (mm)0.34 × 0.27 × 0.22
Data collection
DiffractometerOxford Diffraction Gemini
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.818, 0.877
No. of measured, independent and
observed [I > 2σ(I)] reflections		38087, 5035, 2561
Rint0.069
(sin θ/λ)max (Å−1)0.756
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.168, 1.03
No. of reflections5035
No. of parameters181
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å−3)0.32, −0.39

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···Oi0.952.433.372 (3)169
Symmetry code: (i) −x+1/2, y−1/2, z.
 

Acknowledgements

RJB acknowledges the NSF–MRI program for funding to purchase the X-ray CCD diffractometer.

References

First citationBrandenburg, K. (1998). DIAMOND. Version 2.1. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationJohn, A., Mithun, A., Holla, B. S., Shashikala, H. D., Umesh, G. & Chandrasekharan, K. (2007). Opt. Commun. 296, 235–241.  Google Scholar
 First citationOxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.  Google Scholar
 First citationSheldrick, G. M. (1990). Acta Cryst. A46, 467–473.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationThiruvalluvar, A., Subramanyam, M., Butcher, R. J., Adhikari, A. V. & Karabasanagouda, T. (2007b). Acta Cryst. E63, o4716.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationThiruvalluvar, A., Subramanyam, M., Butcher, R. J., Adhikari, A. V. & Wagle, S. (2007a). Acta Cryst. E63, o4536.  Web of Science CSD CrossRef IUCr Journals 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.

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ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o60
https://doi.org/10.1107/S1600536807062010
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