3-Methyl-5-(4-methyl­phen­yl)cyclo­hex-2-enone

Mohan, R.T.S.; Kamatchi, S.; Subramanyam, M.; Thiruvalluvar, A.; Linden, A.

doi:10.1107/S1600536808013822

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1066

doi:10.1107/S1600536808013822

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3-Methyl-5-(4-methylphenyl)cyclohex-2-enone

R. T. Sabapathy Mohan,^a S. Kamatchi,^a M. Subramanyam,^b A. Thiruvalluvar ^b ^* and A. Linden ^c

^aDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamil Nadu, India, ^bPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamil Nadu, India, and ^cInstitute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland.
^*Correspondence e-mail: athiru@vsnl.net

(Received 5 May 2008; accepted 8 May 2008; online 14 May 2008)

In the title molecule, C₁₄H₁₆O, the cyclohexene ring adopts an envelope conformation, with all substituents equatorial. Molecules are linked by C—H⋯O hydrogen bonds. A C—H⋯π interaction involving the benzene ring is also found in the crystal structure. The H atoms of both methyl groups are disordered equally over two positions.

Related literature

For related literature, see: Padmavathi et al. (2000 ).

Experimental

Crystal data

C₁₄H₁₆O
M_r = 200.27
Monoclinic, P 2₁ /n
a = 5.2623 (3) Å
b = 11.1583 (7) Å
c = 19.3341 (11) Å
β = 94.994 (4)°
V = 1130.96 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 160 (1) K
0.25 × 0.18 × 0.18 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: none
16716 measured reflections
2002 independent reflections
1316 reflections with I > 2σ(I)
R_int = 0.085

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.231
S = 1.09
2002 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.95	2.48	3.425 (3)	173
C5—H5⋯Cgⁱⁱ	1.00	2.94	3.818 (3)	147
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x+1, y, z. Cg is the centroid of the bezene ring.

Data collection: COLLECT (Nonius, 2000 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013822/wn2260sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808013822/wn2260Isup2.hkl

checkCIF report

Comment top

The title compound, has been analysed as part of our crystallographic studies on substituted cyclohexenes. The molecular structure of the title compound, with atomic numbering scheme, is shown in Fig. 1. The cyclohexene ring adopts an envelope conformation, with all substituents equatorial. Molecules are linked by C2—H2···O1(2 - x, 1 - y, 1 - z) hydrogen bonds (Fig. 2). A C—H···π interaction involving the benzene ring is also found in the crystal structure.

Related literature top

For related literature, see: Padmavathi et al. (2000). Cg is the centroid of the bezene ring

Experimental top

The title compound was prepared according to the general procedure reported by Padmavathi et al. (2000). A mixture of 2,4-bis(ethoxycarbonyl)-5-hydroxy-5-methyl-3,4'-methylphenylcyclohexanone (3.62 g, 0.01 mol) in glacial acetic acid (25 ml) and concentrated hydrochloric acid (50 ml) was refluxed for 12 h. After completion of the reaction, the reaction mixture was neutralized with aqueous ammonia and separated using chloroform. The product was purified by column chromatography (benzene-EtOAc, 9.5:0.5 v/v). The yield of the isolated product was 1.07 g (87%).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are represented by spheres of arbitrary radius.
	Fig. 2. The molecular packing of the title compound, viewed down the a axis showing the C—H···O (dashed lines) interactions.

3-Methyl-5-(4-methylphenyl)cyclohex-2-enone top

Crystal data top

C₁₄H₁₆O	F(000) = 432
M_r = 200.27	D_x = 1.176 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 315 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 5.2623 (3) Å	Cell parameters from 2105 reflections
b = 11.1583 (7) Å	θ = 2.0–25.0°
c = 19.3341 (11) Å	µ = 0.07 mm⁻¹
β = 94.994 (4)°	T = 160 K
V = 1130.96 (12) Å³	Prism, colourless
Z = 4	0.25 × 0.18 × 0.18 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	1316 reflections with I > 2σ(I)
Radiation source: Nonius FR590 sealed tube generator	R_int = 0.085
Horizontally mounted graphite crystal monochromator	θ_max = 25.0°, θ_min = 3.7°
Detector resolution: 9 pixels mm^-1	h = 0→6
ω scans with κ offsets	k = 0→13
16716 measured reflections	l = −22→22
2002 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.072	H-atom parameters constrained
wR(F²) = 0.231	w = 1/[σ²(F_o²) + (0.1423P)²] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
2002 reflections	Δρ_max = 0.48 e Å⁻³
137 parameters	Δρ_min = −0.30 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.16 (2)

Crystal data top

C₁₄H₁₆O	V = 1130.96 (12) Å³
M_r = 200.27	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.2623 (3) Å	µ = 0.07 mm⁻¹
b = 11.1583 (7) Å	T = 160 K
c = 19.3341 (11) Å	0.25 × 0.18 × 0.18 mm
β = 94.994 (4)°

Data collection top

Nonius KappaCCD area-detector diffractometer	1316 reflections with I > 2σ(I)
16716 measured reflections	R_int = 0.085
2002 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.231	H-atom parameters constrained
S = 1.09	Δρ_max = 0.48 e Å⁻³
2002 reflections	Δρ_min = −0.30 e Å⁻³
137 parameters

Special details top

Experimental. Solvent used: ? Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.728 (3) Frames collected: 237 Seconds exposure per frame: 18 Degrees rotation per frame: 1.8 Crystal-Detector distance (mm): 30.0

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.8289 (3)	0.60964 (17)	0.42477 (10)	0.0480 (7)
C1	0.6687 (5)	0.5310 (2)	0.41187 (13)	0.0380 (9)
C2	0.6807 (5)	0.4150 (3)	0.44740 (14)	0.0392 (9)
C3	0.5102 (5)	0.3288 (2)	0.43313 (13)	0.0373 (9)
C4	0.2974 (5)	0.3417 (2)	0.37608 (13)	0.0397 (9)
C5	0.3519 (5)	0.4399 (2)	0.32304 (14)	0.0410 (9)
C6	0.4432 (5)	0.5523 (3)	0.36013 (15)	0.0446 (10)
C11	0.1274 (5)	0.4579 (2)	0.26887 (14)	0.0399 (9)
C12	0.0467 (5)	0.3630 (3)	0.22587 (15)	0.0449 (10)
C13	−0.1517 (5)	0.3746 (3)	0.17411 (15)	0.0437 (10)
C14	−0.2758 (5)	0.4829 (2)	0.16303 (13)	0.0386 (9)
C15	−0.1973 (5)	0.5781 (2)	0.20557 (14)	0.0412 (9)
C16	−0.0006 (5)	0.5656 (2)	0.25810 (14)	0.0411 (9)
C21	−0.4928 (5)	0.4965 (3)	0.10693 (15)	0.0505 (10)
C31	0.5112 (6)	0.2145 (2)	0.47430 (15)	0.0496 (10)
H2	0.81624	0.40075	0.48216	0.0471*
H4A	0.27208	0.26420	0.35156	0.0476*
H4B	0.13730	0.36148	0.39696	0.0476*
H5	0.49701	0.41021	0.29761	0.0492*
H6A	0.49029	0.61187	0.32552	0.0536*
H6B	0.30195	0.58644	0.38449	0.0536*
H12	0.13007	0.28779	0.23210	0.0539*
H13	−0.20263	0.30744	0.14604	0.0525*
H15	−0.27932	0.65353	0.19880	0.0494*
H16	0.04671	0.63215	0.28705	0.0493*
H21A	−0.55656	0.57899	0.10675	0.0758*	0.500
H21B	−0.43159	0.47801	0.06168	0.0758*	0.500
H21C	−0.63066	0.44117	0.11600	0.0758*	0.500
H21D	−0.52265	0.41979	0.08287	0.0758*	0.500
H21E	−0.64762	0.52077	0.12794	0.0758*	0.500
H21F	−0.44855	0.55761	0.07362	0.0758*	0.500
H31A	0.37072	0.16309	0.45556	0.0744*	0.500
H31B	0.67370	0.17279	0.47117	0.0744*	0.500
H31C	0.48990	0.23312	0.52299	0.0744*	0.500
H31D	0.65216	0.21624	0.51092	0.0744*	0.500
H31E	0.34918	0.20654	0.49531	0.0744*	0.500
H31F	0.53298	0.14621	0.44349	0.0744*	0.500

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0439 (12)	0.0548 (13)	0.0434 (13)	−0.0079 (10)	−0.0074 (9)	0.0016 (9)
C1	0.0331 (15)	0.0480 (17)	0.0324 (15)	−0.0016 (13)	0.0006 (12)	−0.0033 (12)
C2	0.0340 (14)	0.0505 (17)	0.0324 (15)	0.0048 (13)	−0.0014 (12)	0.0012 (12)
C3	0.0368 (15)	0.0427 (16)	0.0323 (15)	0.0072 (12)	0.0025 (12)	−0.0009 (12)
C4	0.0379 (16)	0.0433 (17)	0.0370 (16)	0.0007 (12)	−0.0012 (12)	0.0020 (12)
C5	0.0421 (16)	0.0400 (16)	0.0393 (16)	0.0006 (12)	−0.0052 (13)	0.0000 (12)
C6	0.0429 (16)	0.0458 (17)	0.0432 (17)	−0.0035 (13)	−0.0076 (13)	0.0081 (13)
C11	0.0393 (16)	0.0390 (16)	0.0399 (16)	−0.0028 (12)	−0.0043 (12)	0.0024 (12)
C12	0.0485 (17)	0.0373 (16)	0.0463 (18)	0.0028 (12)	−0.0114 (14)	−0.0005 (12)
C13	0.0471 (17)	0.0418 (17)	0.0406 (17)	−0.0031 (13)	−0.0058 (13)	−0.0043 (12)
C14	0.0366 (15)	0.0468 (17)	0.0315 (15)	−0.0018 (12)	−0.0024 (11)	0.0029 (12)
C15	0.0403 (16)	0.0424 (16)	0.0395 (17)	0.0052 (12)	−0.0049 (13)	0.0046 (12)
C16	0.0449 (16)	0.0360 (16)	0.0409 (17)	−0.0035 (12)	−0.0042 (13)	−0.0015 (12)
C21	0.0443 (17)	0.065 (2)	0.0398 (17)	0.0002 (15)	−0.0103 (13)	0.0021 (14)
C31	0.0583 (19)	0.0449 (17)	0.0441 (17)	0.0061 (14)	−0.0038 (14)	0.0024 (13)

Geometric parameters (Å, º) top

O1—C1	1.227 (3)	C5—H5	1.0000
C1—C2	1.464 (4)	C6—H6A	0.9900
C1—C6	1.503 (4)	C6—H6B	0.9900
C2—C3	1.328 (4)	C12—H12	0.9500
C3—C4	1.509 (4)	C13—H13	0.9500
C3—C31	1.503 (3)	C15—H15	0.9500
C4—C5	1.545 (3)	C16—H16	0.9500
C5—C6	1.503 (4)	C21—H21A	0.9800
C5—C11	1.522 (4)	C21—H21B	0.9800
C11—C12	1.390 (4)	C21—H21C	0.9800
C11—C16	1.385 (3)	C21—H21D	0.9800
C12—C13	1.388 (4)	C21—H21E	0.9800
C13—C14	1.381 (4)	C21—H21F	0.9800
C14—C15	1.384 (3)	C31—H31A	0.9800
C14—C21	1.513 (4)	C31—H31B	0.9800
C15—C16	1.393 (4)	C31—H31C	0.9800
C2—H2	0.9500	C31—H31D	0.9800
C4—H4A	0.9900	C31—H31E	0.9800
C4—H4B	0.9900	C31—H31F	0.9800

O1···C31ⁱ	3.387 (3)	H4B···H2^v	2.5000
O1···H6Bⁱⁱ	2.6800	H5···C2	2.9700
O1···H13ⁱⁱⁱ	2.6500	H5···C14ⁱⁱ	3.0700
O1···H2^iv	2.4800	H6A···C15ⁱⁱ	2.9800
O1···H31Cⁱ	2.6800	H6A···C16	2.8400
O1···H31Eⁱ	2.7800	H6A···H16	2.4000
C1···C16ⁱⁱ	3.594 (4)	H6A···C12ⁱⁱⁱ	2.9700
C1···C2ⁱ	3.467 (4)	H6A···C13ⁱⁱⁱ	3.0500
C1···C3ⁱ	3.579 (4)	H6A···H12ⁱⁱⁱ	2.3200
C2···C1ⁱ	3.467 (4)	H6A···H13ⁱⁱⁱ	2.4900
C2···C2ⁱ	3.468 (4)	H6B···O1^v	2.6800
C3···C1ⁱ	3.579 (4)	H6B···C16	2.8100
C16···C1^v	3.594 (4)	H6B···H16	2.2700
C31···O1ⁱ	3.387 (3)	H12···C4	2.9100
C1···H31Cⁱ	3.0600	H12···H4A	2.3800
C2···H5	2.9700	H12···H6A^vi	2.3200
C2···H4Bⁱⁱ	2.7400	H12···H16^vi	2.4800
C4···H12	2.9100	H13···H21D	2.3500
C6···H16	2.5700	H13···O1^vi	2.6500
C12···H21Cⁱⁱ	2.9600	H13···H6A^vi	2.4900
C12···H4A	2.8300	H15···H21A	2.3500
C12···H6A^vi	2.9700	H16···C6	2.5700
C13···H6A^vi	3.0500	H16···H6A	2.4000
C14···H5^v	3.0700	H16···H6B	2.2700
C15···H6A^v	2.9800	H16···H12ⁱⁱⁱ	2.4800
C16···H6A	2.8400	H21A···H15	2.3500
C16···H6B	2.8100	H21A···H4A^vii	2.5200
C21···H31Bⁱⁱⁱ	3.0700	H21C···C12^v	2.9600
C21···H31A^vii	2.9100	H21D···H13	2.3500
C31···H21F^vi	3.1000	H21F···C31ⁱⁱⁱ	3.1000
H2···H4Bⁱⁱ	2.5000	H31A···H4A	2.3200
H2···H31D	2.3200	H31A···C21^viii	2.9100
H2···O1^iv	2.4800	H31B···C21^vi	3.0700
H4A···C12	2.8300	H31C···O1ⁱ	2.6800
H4A···H12	2.3800	H31C···C1ⁱ	3.0600
H4A···H31A	2.3200	H31D···H2	2.3200
H4A···H31F	2.5200	H31E···O1ⁱ	2.7800
H4A···H21A^viii	2.5200	H31F···H4A	2.5200
H4B···C2^v	2.7400

O1—C1—C2	122.4 (2)	C15—C16—H16	119.00
O1—C1—C6	120.7 (2)	C14—C21—H21A	109.00
C2—C1—C6	116.8 (2)	C14—C21—H21B	109.00
C1—C2—C3	122.8 (2)	C14—C21—H21C	109.00
C2—C3—C4	121.9 (2)	C14—C21—H21D	109.00
C2—C3—C31	122.2 (2)	C14—C21—H21E	109.00
C4—C3—C31	115.9 (2)	C14—C21—H21F	109.00
C3—C4—C5	112.6 (2)	H21A—C21—H21B	109.00
C4—C5—C6	110.2 (2)	H21A—C21—H21C	110.00
C4—C5—C11	111.9 (2)	H21A—C21—H21D	141.00
C6—C5—C11	114.5 (2)	H21A—C21—H21E	56.00
C1—C6—C5	112.8 (2)	H21A—C21—H21F	56.00
C5—C11—C12	119.3 (2)	H21B—C21—H21C	109.00
C5—C11—C16	123.8 (2)	H21B—C21—H21D	56.00
C12—C11—C16	116.9 (2)	H21B—C21—H21E	141.00
C11—C12—C13	122.1 (3)	H21B—C21—H21F	56.00
C12—C13—C14	120.6 (3)	H21C—C21—H21D	56.00
C13—C14—C15	117.8 (2)	H21C—C21—H21E	56.00
C13—C14—C21	121.1 (2)	H21C—C21—H21F	141.00
C15—C14—C21	121.1 (2)	H21D—C21—H21E	109.00
C14—C15—C16	121.4 (2)	H21D—C21—H21F	109.00
C11—C16—C15	121.2 (2)	H21E—C21—H21F	110.00
C1—C2—H2	119.00	C3—C31—H31A	109.00
C3—C2—H2	119.00	C3—C31—H31B	109.00
C3—C4—H4A	109.00	C3—C31—H31C	109.00
C3—C4—H4B	109.00	C3—C31—H31D	109.00
C5—C4—H4A	109.00	C3—C31—H31E	109.00
C5—C4—H4B	109.00	C3—C31—H31F	109.00
H4A—C4—H4B	108.00	H31A—C31—H31B	109.00
C4—C5—H5	107.00	H31A—C31—H31C	109.00
C6—C5—H5	107.00	H31A—C31—H31D	141.00
C11—C5—H5	107.00	H31A—C31—H31E	56.00
C1—C6—H6A	109.00	H31A—C31—H31F	56.00
C1—C6—H6B	109.00	H31B—C31—H31C	109.00
C5—C6—H6A	109.00	H31B—C31—H31D	56.00
C5—C6—H6B	109.00	H31B—C31—H31E	141.00
H6A—C6—H6B	108.00	H31B—C31—H31F	56.00
C11—C12—H12	119.00	H31C—C31—H31D	56.00
C13—C12—H12	119.00	H31C—C31—H31E	56.00
C12—C13—H13	120.00	H31C—C31—H31F	141.00
C14—C13—H13	120.00	H31D—C31—H31E	109.00
C14—C15—H15	119.00	H31D—C31—H31F	109.00
C16—C15—H15	119.00	H31E—C31—H31F	109.00
C11—C16—H16	119.00

O1—C1—C2—C3	−179.1 (3)	C4—C5—C11—C16	120.6 (3)
C6—C1—C2—C3	3.3 (4)	C6—C5—C11—C12	172.5 (2)
O1—C1—C6—C5	149.3 (2)	C6—C5—C11—C16	−5.7 (4)
C2—C1—C6—C5	−33.1 (3)	C5—C11—C12—C13	−178.0 (3)
C1—C2—C3—C4	3.3 (4)	C16—C11—C12—C13	0.4 (4)
C1—C2—C3—C31	−174.4 (2)	C5—C11—C16—C15	177.0 (2)
C2—C3—C4—C5	19.3 (3)	C12—C11—C16—C15	−1.3 (4)
C31—C3—C4—C5	−162.8 (2)	C11—C12—C13—C14	0.6 (4)
C3—C4—C5—C6	−47.3 (3)	C12—C13—C14—C15	−0.7 (4)
C3—C4—C5—C11	−175.9 (2)	C12—C13—C14—C21	−179.8 (3)
C4—C5—C6—C1	54.2 (3)	C13—C14—C15—C16	−0.3 (4)
C11—C5—C6—C1	−178.6 (2)	C21—C14—C15—C16	178.9 (2)
C4—C5—C11—C12	−61.2 (3)	C14—C15—C16—C11	1.3 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x+2, −y+1, −z+1; (v) x−1, y, z; (vi) −x+1/2, y−1/2, −z+1/2; (vii) −x−1/2, y+1/2, −z+1/2; (viii) −x−1/2, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1^iv	0.95	2.48	3.425 (3)	173
C5—H5···Cgⁱⁱ	1.00	2.94	3.818 (3)	147

Symmetry codes: (ii) x+1, y, z; (iv) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₆O
M_r	200.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	160
a, b, c (Å)	5.2623 (3), 11.1583 (7), 19.3341 (11)
β (°)	94.994 (4)
V (Å³)	1130.96 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.25 × 0.18 × 0.18

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16716, 2002, 1316
R_int	0.085
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.231, 1.09
No. of reflections	2002
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.30

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.95	2.48	3.425 (3)	173
C5—H5···Cgⁱⁱ	1.00	2.94	3.818 (3)	147

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y, z.

Acknowledgements

AT thanks the UGC, India, for the award of a Minor Research Project [File No. MRP-2355/06(UGC-SERO), Link No. 2355, 10/01/2007].

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. London: Academic Press. Google Scholar
Padmavathi, V., Jagan Mohan Reddy, B., Balaih, A., Venugopal Reddy, K. & Bhasker Reddy, D. (2000). Molecules. 5, 1281–1286. CrossRef CAS Google Scholar
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Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar