1,3-Dimethyl-2,6-diphenyl­piperidin-4-one

Nithya, P.; Hathwar, V.R.; Maiyalagan, T.; Kazak, C.; Nawaz Khan, F.

doi:10.1107/S1600536809003419

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o439

doi:10.1107/S1600536809003419

Open

access

1,3-Dimethyl-2,6-diphenylpiperidin-4-one

P. Nithya,^a Venkatesha R. Hathwar,^b T. Maiyalagan,^a Canan Kazak ^c and F. Nawaz Khan ^a ^*

^aChemistry Division, School of Science and Humanities, VIT University, Vellore 632 014, Tamil Nadu, India, ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and ^cOndokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, 55139 Samsun, Turkey
^*Correspondence e-mail: nawaz_f@yahoo.co.in

(Received 22 January 2009; accepted 28 January 2009; online 31 January 2009)

In the title moleclue, C₁₉H₂₁NO, the 4-piperidone ring adopts a chair conformation in which the two benzene rings and the methyl group attached to C atoms all have equatorial orientations. In the crystal structure, centrosymmetric dimers are formed through weak intermolecular C—H⋯O hydrogen bonds [the dihedral angle between the aromatic rings is 58.51 (5)°].

Related literature

For general background, see: Badorrey et al. (1999 ); Grishina et al. (1994 ); Nalanishi et al. (1974 ); Perumal et al. (2001 ); Ponnuswamy et al. (2002 ). For a related crystal structure, see: Gayathri et al. (2008 ). For the synthetis, see: Noller & Baliah (1948 ). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ); Nardelli (1983 , 1995 ).

Experimental

Crystal data

C₁₉H₂₁NO
M_r = 279.37
Triclinic, $[P \overline 1]$
a = 5.9201 (2) Å
b = 10.9749 (3) Å
c = 12.8247 (3) Å
α = 80.2961 (12)°
β = 86.673 (2)°
γ = 76.4499 (11)°
V = 798.30 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 290 (2) K
0.28 × 0.21 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.943, T_max = 0.987
12316 measured reflections
3143 independent reflections
2446 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.116
S = 1.02
3143 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1ⁱ	0.98	2.56	3.3535 (16)	139
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003419/lh2761sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003419/lh2761Isup2.hkl

checkCIF report

Comment top

The synthesis of 4-piperidones is of current interest due to their potential medical applications (Grishina et al., 1994, Ponnuswamy et al., 2002). 4-Piperidones have been found to exhibit blood cholesterol-lowering activities (Nalanishi et al., 1974). Various piperidones and piperidine derivatives are present in numerous alkaloids (Badorrey et al., 1999). Piperidones are also reported to possess analgesic, anti-inflammatory, central nervous system (CNS), local anaesthetic, anticancer and antimicrobial activity (Perumal et al., 2001).

In the title molecule, C₁₉H₂₀NO (Fig. 1), the piperidine ring adopts a chair conformation (Cremer & Pople, 1975; Nardelli, 1995). The phenyl rings at positions 2 and 6 and the methyl group attached at position 3 all have equatorial orientations. In the related crystal structure of r-2,c-6-Bis(4-chlorophenyl)-t-3-isopropyl-1-nitrosopiperidin-4-one, the piperidine ring also adopts a chair conformation (Gayathri et al., 2008) but the three substituents on the C atoms of the ring are in axial orientations. In the crystal structure, centrosymmetric dimers are formed through weak intermolecular C—H···O hydrogen bonds (Fig. 2).

Related literature top

For general background, see: Badorrey et al. (1999); Grishina et al. (1994); Nalanishi et al. (1974); Perumal et al. (2001); Ponnuswamy et al. (2002). For a related crystal structure, see: Gayathri et al. (2008). For the synthetis, see: Noller & Baliah (1948). For puckering and asymmetry parameters, see: Cremer & Pople (1975); Nardelli (1983, 1995).

Experimental top

The sythesis was based on a procedure in the literature (Noller & Baliah, 1948). Benzaldehyde (0.20 mol), 3-methyl-2-butanone (0.10 mol) and ammonium acetate (0.10 mol) were dissolved in 80 ml of distilled ethanol and heated over a boiling water bath, with shaking until a yellow colour developed and ultimately changed to orange. The solution was left undisturbed for 14 h. The precipitated solid was filtered and purified by recrystallization from ethanol. The piperidone intermediate was then dissolved in acetone and was alkyalted with methyliodide in the presence of potassium carbonate.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of (I) shown with 50% probability displacement ellipsoids.
	Fig. 2. Part of the crystal structure of (I) with dashed lines indicating intermolecular C—H···O hydrogen bonds.

1,3-Dimethyl-2,6-diphenylpiperidin-4-one top

Crystal data top

C₁₉H₂₁NO	Z = 2
M_r = 279.37	F(000) = 300
Triclinic, P1	D_x = 1.162 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9201 (2) Å	Cell parameters from 873 reflections
b = 10.9749 (3) Å	θ = 1.9–20.8°
c = 12.8247 (3) Å	µ = 0.07 mm⁻¹
α = 80.2961 (12)°	T = 290 K
β = 86.673 (2)°	Block, colorless
γ = 76.4499 (11)°	0.28 × 0.21 × 0.18 mm
V = 798.30 (4) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3143 independent reflections
Radiation source: fine-focus sealed tube	2446 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→7
T_min = 0.943, T_max = 0.987	k = −13→13
12316 measured reflections	l = −15→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0539P)² + 0.1409P] where P = (F_o² + 2F_c²)/3
3143 reflections	(Δ/σ)_max < 0.001
192 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₉H₂₁NO	γ = 76.4499 (11)°
M_r = 279.37	V = 798.30 (4) Å³
Triclinic, P1	Z = 2
a = 5.9201 (2) Å	Mo Kα radiation
b = 10.9749 (3) Å	µ = 0.07 mm⁻¹
c = 12.8247 (3) Å	T = 290 K
α = 80.2961 (12)°	0.28 × 0.21 × 0.18 mm
β = 86.673 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3143 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2446 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.987	R_int = 0.019
12316 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.02	Δρ_max = 0.14 e Å⁻³
3143 reflections	Δρ_min = −0.15 e Å⁻³
192 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

	x	y	z	U_iso*/U_eq
N1	0.17010 (18)	0.40892 (9)	0.73876 (8)	0.0419 (3)
O1	0.25711 (17)	0.47960 (11)	1.03053 (7)	0.0615 (3)
C1	0.1134 (2)	0.54013 (12)	0.76264 (10)	0.0419 (3)
H1	−0.0457	0.5582	0.7916	0.050*
C2	0.2788 (3)	0.55376 (14)	0.84570 (11)	0.0532 (4)
H2A	0.4336	0.5475	0.8146	0.064*
H2B	0.2276	0.6370	0.8665	0.064*
C3	0.2882 (2)	0.45443 (14)	0.94154 (10)	0.0485 (3)
C4	0.3367 (3)	0.32119 (14)	0.91755 (11)	0.0532 (4)
H4	0.4923	0.3030	0.8850	0.064*
C5	0.1607 (2)	0.31444 (12)	0.83478 (10)	0.0432 (3)
H5	0.0040	0.3339	0.8661	0.052*
C6	0.2066 (2)	0.18211 (12)	0.80603 (10)	0.0467 (3)
C7	0.4060 (3)	0.13480 (14)	0.75020 (12)	0.0571 (4)
H7	0.5153	0.1837	0.7319	0.069*
C8	0.4446 (3)	0.01556 (15)	0.72124 (14)	0.0711 (5)
H8	0.5799	−0.0148	0.6840	0.085*
C9	0.2867 (4)	−0.05793 (15)	0.74677 (15)	0.0748 (5)
H9	0.3126	−0.1374	0.7261	0.090*
C10	0.0903 (4)	−0.01377 (16)	0.80298 (17)	0.0791 (5)
H10	−0.0170	−0.0639	0.8214	0.095*
C11	0.0495 (3)	0.10595 (15)	0.83308 (14)	0.0656 (4)
H11	−0.0846	0.1348	0.8717	0.079*
C12	0.1264 (2)	0.63589 (12)	0.66384 (10)	0.0428 (3)
C13	−0.0613 (3)	0.73494 (13)	0.63339 (12)	0.0536 (4)
H13	−0.1987	0.7419	0.6733	0.064*
C14	−0.0475 (3)	0.82404 (14)	0.54407 (13)	0.0658 (4)
H14	−0.1752	0.8902	0.5245	0.079*
C15	0.1535 (3)	0.81493 (15)	0.48471 (13)	0.0675 (5)
H15	0.1629	0.8751	0.4252	0.081*
C16	0.3413 (3)	0.71672 (17)	0.51319 (13)	0.0687 (5)
H16	0.4776	0.7101	0.4725	0.082*
C17	0.3284 (3)	0.62776 (15)	0.60201 (12)	0.0579 (4)
H17	0.4565	0.5616	0.6207	0.070*
C18	0.0031 (3)	0.39902 (14)	0.66175 (12)	0.0623 (4)
H18A	−0.1504	0.4132	0.6928	0.093*
H18B	0.0439	0.3158	0.6422	0.093*
H18C	0.0069	0.4616	0.5999	0.093*
C19	0.3365 (4)	0.22361 (19)	1.01678 (14)	0.0942 (7)
H19A	0.4369	0.2368	1.0679	0.141*
H19B	0.3910	0.1398	0.9993	0.141*
H19C	0.1814	0.2326	1.0458	0.141*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0505 (6)	0.0408 (5)	0.0341 (6)	−0.0089 (5)	−0.0065 (4)	−0.0056 (4)
O1	0.0534 (6)	0.0987 (8)	0.0390 (6)	−0.0236 (5)	0.0017 (4)	−0.0217 (5)
C1	0.0439 (7)	0.0439 (7)	0.0377 (7)	−0.0076 (5)	−0.0009 (5)	−0.0097 (5)
C2	0.0664 (9)	0.0558 (8)	0.0426 (8)	−0.0190 (7)	−0.0068 (6)	−0.0132 (6)
C3	0.0408 (7)	0.0708 (9)	0.0369 (7)	−0.0152 (6)	−0.0045 (5)	−0.0120 (6)
C4	0.0567 (8)	0.0602 (8)	0.0391 (7)	−0.0083 (7)	−0.0098 (6)	−0.0021 (6)
C5	0.0426 (7)	0.0471 (7)	0.0378 (7)	−0.0091 (5)	0.0007 (5)	−0.0032 (5)
C6	0.0483 (8)	0.0455 (7)	0.0437 (7)	−0.0102 (6)	−0.0050 (6)	0.0006 (6)
C7	0.0632 (9)	0.0483 (8)	0.0588 (9)	−0.0138 (7)	0.0082 (7)	−0.0069 (7)
C8	0.0846 (12)	0.0519 (9)	0.0729 (11)	−0.0073 (8)	0.0069 (9)	−0.0134 (8)
C9	0.0964 (14)	0.0446 (8)	0.0832 (12)	−0.0136 (9)	−0.0167 (10)	−0.0081 (8)
C10	0.0831 (13)	0.0558 (9)	0.1021 (14)	−0.0323 (9)	−0.0123 (11)	0.0036 (10)
C11	0.0572 (9)	0.0586 (9)	0.0795 (11)	−0.0193 (7)	0.0017 (8)	0.0004 (8)
C12	0.0511 (7)	0.0410 (6)	0.0388 (7)	−0.0118 (5)	−0.0038 (5)	−0.0105 (5)
C13	0.0614 (9)	0.0448 (7)	0.0522 (8)	−0.0046 (6)	−0.0024 (6)	−0.0112 (6)
C14	0.0908 (12)	0.0407 (7)	0.0607 (10)	−0.0037 (7)	−0.0145 (9)	−0.0052 (7)
C15	0.1055 (14)	0.0528 (9)	0.0486 (9)	−0.0318 (9)	−0.0065 (9)	0.0003 (7)
C16	0.0750 (11)	0.0822 (11)	0.0516 (9)	−0.0312 (9)	0.0058 (8)	−0.0018 (8)
C17	0.0536 (9)	0.0651 (9)	0.0509 (9)	−0.0106 (7)	0.0006 (6)	−0.0018 (7)
C18	0.0852 (11)	0.0505 (8)	0.0540 (9)	−0.0167 (7)	−0.0292 (8)	−0.0049 (7)
C19	0.146 (2)	0.0797 (12)	0.0527 (11)	−0.0258 (12)	−0.0310 (11)	0.0125 (9)

Geometric parameters (Å, º) top

N1—C18	1.4711 (16)	C9—C10	1.365 (3)
N1—C5	1.4777 (15)	C9—H9	0.9300
N1—C1	1.4800 (15)	C10—C11	1.395 (2)
O1—C3	1.2128 (15)	C10—H10	0.9300
C1—C12	1.5145 (18)	C11—H11	0.9300
C1—C2	1.5363 (18)	C12—C13	1.3820 (19)
C1—H1	0.9800	C12—C17	1.390 (2)
C2—C3	1.493 (2)	C13—C14	1.387 (2)
C2—H2A	0.9700	C13—H13	0.9300
C2—H2B	0.9700	C14—C15	1.367 (2)
C3—C4	1.503 (2)	C14—H14	0.9300
C4—C19	1.519 (2)	C15—C16	1.372 (2)
C4—C5	1.5520 (18)	C15—H15	0.9300
C4—H4	0.9800	C16—C17	1.381 (2)
C5—C6	1.5175 (18)	C16—H16	0.9300
C5—H5	0.9800	C17—H17	0.9300
C6—C11	1.383 (2)	C18—H18A	0.9600
C6—C7	1.384 (2)	C18—H18B	0.9600
C7—C8	1.384 (2)	C18—H18C	0.9600
C7—H7	0.9300	C19—H19A	0.9600
C8—C9	1.364 (3)	C19—H19B	0.9600
C8—H8	0.9300	C19—H19C	0.9600

C18—N1—C5	109.46 (10)	C8—C9—C10	119.37 (16)
C18—N1—C1	108.63 (10)	C8—C9—H9	120.3
C5—N1—C1	111.85 (9)	C10—C9—H9	120.3
N1—C1—C12	111.33 (10)	C9—C10—C11	120.50 (16)
N1—C1—C2	110.45 (10)	C9—C10—H10	119.7
C12—C1—C2	109.68 (10)	C11—C10—H10	119.7
N1—C1—H1	108.4	C6—C11—C10	120.59 (16)
C12—C1—H1	108.4	C6—C11—H11	119.7
C2—C1—H1	108.4	C10—C11—H11	119.7
C3—C2—C1	112.04 (11)	C13—C12—C17	118.07 (13)
C3—C2—H2A	109.2	C13—C12—C1	120.95 (12)
C1—C2—H2A	109.2	C17—C12—C1	120.97 (12)
C3—C2—H2B	109.2	C12—C13—C14	120.86 (15)
C1—C2—H2B	109.2	C12—C13—H13	119.6
H2A—C2—H2B	107.9	C14—C13—H13	119.6
O1—C3—C2	122.76 (13)	C15—C14—C13	120.18 (15)
O1—C3—C4	123.25 (13)	C15—C14—H14	119.9
C2—C3—C4	113.99 (11)	C13—C14—H14	119.9
C3—C4—C19	112.28 (13)	C14—C15—C16	119.84 (15)
C3—C4—C5	108.87 (11)	C14—C15—H15	120.1
C19—C4—C5	112.70 (13)	C16—C15—H15	120.1
C3—C4—H4	107.6	C15—C16—C17	120.21 (16)
C19—C4—H4	107.6	C15—C16—H16	119.9
C5—C4—H4	107.6	C17—C16—H16	119.9
N1—C5—C6	110.17 (10)	C16—C17—C12	120.83 (14)
N1—C5—C4	110.93 (10)	C16—C17—H17	119.6
C6—C5—C4	110.79 (10)	C12—C17—H17	119.6
N1—C5—H5	108.3	N1—C18—H18A	109.5
C6—C5—H5	108.3	N1—C18—H18B	109.5
C4—C5—H5	108.3	H18A—C18—H18B	109.5
C11—C6—C7	117.95 (13)	N1—C18—H18C	109.5
C11—C6—C5	121.26 (13)	H18A—C18—H18C	109.5
C7—C6—C5	120.78 (12)	H18B—C18—H18C	109.5
C6—C7—C8	120.81 (15)	C4—C19—H19A	109.5
C6—C7—H7	119.6	C4—C19—H19B	109.5
C8—C7—H7	119.6	H19A—C19—H19B	109.5
C9—C8—C7	120.77 (17)	C4—C19—H19C	109.5
C9—C8—H8	119.6	H19A—C19—H19C	109.5
C7—C8—H8	119.6	H19B—C19—H19C	109.5

C18—N1—C1—C12	−59.74 (14)	N1—C5—C6—C7	55.01 (16)
C5—N1—C1—C12	179.33 (10)	C4—C5—C6—C7	−68.12 (16)
C18—N1—C1—C2	178.16 (11)	C11—C6—C7—C8	0.9 (2)
C5—N1—C1—C2	57.22 (13)	C5—C6—C7—C8	−178.08 (14)
N1—C1—C2—C3	−52.14 (15)	C6—C7—C8—C9	0.2 (3)
C12—C1—C2—C3	−175.21 (11)	C7—C8—C9—C10	−1.1 (3)
C1—C2—C3—O1	−127.65 (13)	C8—C9—C10—C11	0.8 (3)
C1—C2—C3—C4	51.65 (16)	C7—C6—C11—C10	−1.1 (2)
O1—C3—C4—C19	1.3 (2)	C5—C6—C11—C10	177.82 (14)
C2—C3—C4—C19	−178.02 (14)	C9—C10—C11—C6	0.3 (3)
O1—C3—C4—C5	126.78 (13)	N1—C1—C12—C13	124.49 (13)
C2—C3—C4—C5	−52.51 (15)	C2—C1—C12—C13	−112.96 (14)
C18—N1—C5—C6	56.39 (14)	N1—C1—C12—C17	−56.44 (15)
C1—N1—C5—C6	176.84 (10)	C2—C1—C12—C17	66.11 (15)
C18—N1—C5—C4	179.44 (11)	C17—C12—C13—C14	−0.4 (2)
C1—N1—C5—C4	−60.11 (13)	C1—C12—C13—C14	178.66 (12)
C3—C4—C5—N1	55.96 (14)	C12—C13—C14—C15	0.0 (2)
C19—C4—C5—N1	−178.79 (13)	C13—C14—C15—C16	0.5 (2)
C3—C4—C5—C6	178.65 (11)	C14—C15—C16—C17	−0.5 (2)
C19—C4—C5—C6	−56.09 (17)	C15—C16—C17—C12	0.0 (2)
N1—C5—C6—C11	−123.92 (14)	C13—C12—C17—C16	0.5 (2)
C4—C5—C6—C11	112.95 (15)	C1—C12—C17—C16	−178.65 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1ⁱ	0.98	2.56	3.3535 (16)	139

Symmetry code: (i) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₁NO
M_r	279.37
Crystal system, space group	Triclinic, P1
Temperature (K)	290
a, b, c (Å)	5.9201 (2), 10.9749 (3), 12.8247 (3)
α, β, γ (°)	80.2961 (12), 86.673 (2), 76.4499 (11)
V (Å³)	798.30 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.28 × 0.21 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.943, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	12316, 3143, 2446
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.116, 1.02
No. of reflections	3143
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.15

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1ⁱ	0.98	2.56	3.3535 (16)	138.5

Symmetry code: (i) −x, −y+1, −z+2.

Acknowledgements

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA–DST program at the IISc. We thank Professor T. N. Guru Row, IISc, Bangalore, for useful crystallographic discussions. FNK thanks the DST for Fast Track Proposal funding.

References

Badorrey, R., Cativiela, C., Diaz-de-Villegas, M. D. & Galvez, J. A. (1999). Tetrahedron, 55, 7601–7612. Web of Science CrossRef CAS Google Scholar
Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gayathri, P., Thiruvalluvar, A., Manimekalai, A., Sivakumar, S. & Butcher, R. J. (2008). Acta Cryst. E64, o1973. Web of Science CSD CrossRef IUCr Journals Google Scholar
Grishina, G. V., Gaidarova, E. L. & Zefirov, N. S. (1994). Chem. Heterocycl. Compd. 30, 401–1426. Google Scholar
Nalanishi, M., Shiraki, M., Kobayakawa, T. & Kobayashi, R. (1974). Jpn Patent 74-03987. Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Noller, C. & Baliah, V. (1948). J. Am. Chem. Soc. 70, 3853–3855. CrossRef PubMed CAS Web of Science Google Scholar
Perumal, R. V., Agiraj, M. & Shanmugapandiyan, P. (2001). Indian Drugs, 38, 156–159. Google Scholar
Ponnuswamy, S., Venkatraj, M., Jeyaraman, R., Suresh Kumar, M., Kumaran, D. & Ponnuswamy, M. N. (2002). Indian J. Chem. Sect. B, 41, 614–627. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar