(E)-6-Methyl-3-(2-methyl­benzyl­idene)­chroman-2-one

Vijayakumar, S.; Murugavel, S.; Kannan, D.; Bakthadoss, M.

doi:10.1107/S1600536812005624

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o791

doi:10.1107/S1600536812005624

Open

access

(E)-6-Methyl-3-(2-methylbenzylidene)chroman-2-one

S. Vijayakumar,^a S. Murugavel,^b ^* D. Kannan ^c and M. Bakthadoss ^c ‡

^aDepartment of Physics, Sri Balaji Chokkalingam Engineering College, Arni, Thiruvannamalai 632 317, India, ^bDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, and ^cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
^*Correspondence e-mail: smurugavel27@gmail.com

(Received 23 January 2012; accepted 8 February 2012; online 24 February 2012)

In the title compound, C₁₈H₁₆O₂, the heterocyclic ring of the chroman-2-one system adopts a slightly distorted screw-boat conformation. The dihedral angle between the least-squares planes of the coumarin ring system and the benzene ring is 67.5 (1)°. The crystal packing features C—H⋯O hydrogen bonds, which link the molecules into centrosymmetric R₂²(8) dimers, and C—H⋯π interactions.

Related literature

For the biological activity of coumarins, see: Sharma et al. (2005 ); Iqbal et al. (2009 ); Siddiqui et al. (2009 ); Vyas et al. (2009 ); Rollinger et al. (2004 ); Brühlmann et al. (2001 ). For ring-puckering parameters, see: Cremer & Pople (1975 ). For closely related structures, see: Choi & Kim (2010 ); Peng et al. (2012 ).

Experimental

Crystal data

C₁₈H₁₆O₂
M_r = 264.31
Monoclinic, P 2₁ /c
a = 9.1331 (2) Å
b = 17.8838 (5) Å
c = 9.6443 (3) Å
β = 118.056 (1)°
V = 1390.14 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.21 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.983, T_max = 0.987
17986 measured reflections
4246 independent reflections
2882 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.152
S = 1.00
4246 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1ⁱ	0.93	2.53	3.437 (2)	167
C14—H14⋯Cgⁱⁱ	0.93	2.88	3.611 (2)	137
C18—H18A⋯Cgⁱⁱⁱ	0.96	2.74	3.490 (2)	136
Symmetry codes: (i) -x, -y+1, -z+2; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); 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: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812005624/gk2454sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005624/gk2454Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005624/gk2454Isup3.cml

checkCIF report

Comment top

Coumarins are very well known for their biological activity, such as antioxidant (Sharma et al., 2005), antiamoebic (Iqbal et al., 2009), anticonvulsant (Siddiqui et al., 2009), antimicrobial (Vyas et al., 2009) and inhibitions of acetylcholinesterase and monoamine oxidase (Rollinger et al., 2004; Brühlmann et al., 2001). In view of this importance, the crystal structure of the title compound has been carried out and the results are presented here.

Fig. 1. shows a displacement ellipsoid plot of of the title compound, with the atom numbering scheme. The pyranone ring adopts a distorted screw-boat conformation as indicated from the puckering parameters (Cremer & Pople, 1975): Q = 0.3229 (15) Å, θ = 72.1 (3)° and ϕ = 154.8 (3)°. The dihedral angle between the least-squares planes of the coumarine ring system (O1/C8–C16) and the benzene ring (C1–C6) is 67.5 (1)°. The geometric parameters of the title molecule agree well with those reported for similar structures (Choi & Kim, 2010; Peng et al., 2012).

The crystal packing (Fig. 2) is stabilized by intermolecular C—H···O hydrogen bonds. The molecules at x, y, z and -x, 1-y, 2-z are linked by C11—H11···O1 hydrogen bonds through cyclic centrosymmetric R₂²(8) motifs (See Table 1; first entry). The crystal packing (Fig. 3) is further stabilized by C—H···π interactions (See Table 1; second and third entry, Cg is the centroid of the C1–C6 benzene ring).

Related literature top

For the biological activity of coumarins, see: Sharma et al. (2005); Iqbal et al. (2009); Siddiqui et al. (2009); Vyas et al. (2009); Rollinger et al. (2004); Brühlmann et al. (2001). For ring-puckering parameters, see: Cremer & Pople (1975). For closely related structures, see: Choi & Kim (2010); Peng et al. (2012).

Experimental top

A solution of methyl 2-[hydroxy(2-methylphenyl)methyl]prop-2-enoate (0.206 g, 1 mmol) and p-cresol (0.108 g, 1 mmol) in CH₂Cl₂ solvent was allowed to cool at 0^oC. To this solution, concentrated H₂SO₄ (0.98 g, 1 mmol) was added, and then stirred well at room temperature. After the completion of the reaction, as indicated by TLC, the reaction mixture was quenched with 1 M sodium bicarbonate and then extracted with CH₂Cl₂. The combined organic layers were washed with brine (2 X 10 ml) and dried over anhydrous sodium sulfate. The organic layer was evaporated and the residue was purified by column chromatography on silicagel (100–200) mesh, using ethylacetate and hexanes (1:9) as solvents. The pure title compound was obtained as a colourless solid (0.169 g, 64.5% yield, m.p. 407–409K). Recrystallization was carried out using ethyl acetate as solvent.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. Part of the crystal structure of the title compound showing C—H···O intermolecular hydrogen bonds (dotted lines) generating R²₂(8) centrosymmetric dimer. [Symmetry code: (i) -x, 1-y, 2-z].
	Fig. 3. A view of the C-H···π interactions(dotted lines) in the crystal stucture of the title compound. H atoms not participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (ii) x, 3/2-y, 1/2+z; (iii) 1-x, 1-y, 1-z; (iv) x, 3/2-y, -1/2+z; (v) 1-x, -1/2-y, 3/2-z].

(E)-6-Methyl-3-(2-methylbenzylidene)chroman-2-one top

Crystal data top

C₁₈H₁₆O₂	F(000) = 560
M_r = 264.31	D_x = 1.263 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4254 reflections
a = 9.1331 (2) Å	θ = 2.3–30.6°
b = 17.8838 (5) Å	µ = 0.08 mm⁻¹
c = 9.6443 (3) Å	T = 293 K
β = 118.056 (1)°	Block, colourless
V = 1390.14 (7) Å³	0.21 × 0.18 × 0.16 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4246 independent reflections
Radiation source: fine-focus sealed tube	2882 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 10.0 pixels mm^-1	θ_max = 30.6°, θ_min = 2.3°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −25→24
T_min = 0.983, T_max = 0.987	l = −13→13
17986 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0777P)² + 0.1937P] where P = (F_o² + 2F_c²)/3
4246 reflections	(Δ/σ)_max < 0.001
183 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₈H₁₆O₂	V = 1390.14 (7) Å³
M_r = 264.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.1331 (2) Å	µ = 0.08 mm⁻¹
b = 17.8838 (5) Å	T = 293 K
c = 9.6443 (3) Å	0.21 × 0.18 × 0.16 mm
β = 118.056 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4246 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2882 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.987	R_int = 0.026
17986 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.00	Δρ_max = 0.27 e Å⁻³
4246 reflections	Δρ_min = −0.17 e Å⁻³
183 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.53567 (17)	0.64217 (8)	0.67561 (18)	0.0510 (3)
H1	0.5781	0.6520	0.7823	0.061*
C2	0.59366 (19)	0.68218 (9)	0.5898 (2)	0.0591 (4)
H2	0.6741	0.7188	0.6381	0.071*
C3	0.53207 (19)	0.66771 (9)	0.4322 (2)	0.0600 (4)
H3	0.5697	0.6950	0.3732	0.072*
C4	0.41464 (18)	0.61275 (9)	0.36193 (17)	0.0556 (4)
H4	0.3749	0.6030	0.2555	0.067*
C5	0.35357 (16)	0.57122 (7)	0.44610 (15)	0.0457 (3)
C6	0.41463 (15)	0.58712 (7)	0.60612 (15)	0.0426 (3)
C7	0.35620 (16)	0.54362 (7)	0.69924 (15)	0.0440 (3)
H7	0.3418	0.4926	0.6783	0.053*
C8	0.32126 (15)	0.56882 (7)	0.81078 (15)	0.0426 (3)
C9	0.26659 (17)	0.51217 (7)	0.88834 (15)	0.0470 (3)
C10	0.12384 (16)	0.61012 (7)	0.94804 (14)	0.0428 (3)
C11	0.00149 (17)	0.62388 (8)	0.99062 (16)	0.0507 (3)
H11	−0.0461	0.5848	1.0190	0.061*
C12	−0.04862 (17)	0.69606 (8)	0.99036 (17)	0.0506 (3)
H12	−0.1301	0.7056	1.0200	0.061*
C13	0.01926 (16)	0.75525 (8)	0.94698 (16)	0.0468 (3)
C14	0.14082 (16)	0.73905 (7)	0.90318 (16)	0.0456 (3)
H14	0.1866	0.7780	0.8724	0.055*
C15	0.19582 (15)	0.66685 (7)	0.90391 (14)	0.0407 (3)
C16	0.33081 (18)	0.64851 (7)	0.86226 (17)	0.0477 (3)
H16A	0.3215	0.6813	0.7784	0.057*
H16B	0.4379	0.6573	0.9528	0.057*
C17	−0.0374 (2)	0.83405 (9)	0.9463 (2)	0.0661 (4)
H17A	−0.1247	0.8461	0.8435	0.099*
H17B	0.0540	0.8677	0.9733	0.099*
H17C	−0.0777	0.8388	1.0216	0.099*
C18	0.22451 (19)	0.51259 (9)	0.36486 (18)	0.0593 (4)
H18A	0.2632	0.4656	0.4177	0.089*
H18B	0.2034	0.5080	0.2579	0.089*
H18C	0.1240	0.5265	0.3668	0.089*
O1	0.17722 (13)	0.53607 (5)	0.95982 (12)	0.0540 (3)
O2	0.29341 (16)	0.44612 (6)	0.89344 (14)	0.0657 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0488 (7)	0.0557 (8)	0.0530 (8)	−0.0030 (6)	0.0276 (6)	−0.0087 (6)
C2	0.0545 (8)	0.0572 (9)	0.0757 (10)	−0.0044 (6)	0.0391 (8)	−0.0037 (7)
C3	0.0585 (8)	0.0652 (10)	0.0695 (10)	0.0134 (7)	0.0409 (8)	0.0153 (8)
C4	0.0566 (8)	0.0666 (9)	0.0459 (7)	0.0176 (7)	0.0260 (7)	0.0064 (7)
C5	0.0444 (6)	0.0468 (7)	0.0454 (7)	0.0118 (5)	0.0206 (6)	−0.0015 (5)
C6	0.0424 (6)	0.0421 (6)	0.0455 (7)	0.0048 (5)	0.0225 (5)	−0.0027 (5)
C7	0.0457 (6)	0.0388 (6)	0.0448 (7)	−0.0012 (5)	0.0190 (5)	−0.0038 (5)
C8	0.0449 (6)	0.0395 (6)	0.0417 (6)	−0.0049 (5)	0.0189 (5)	−0.0025 (5)
C9	0.0544 (7)	0.0410 (7)	0.0426 (7)	−0.0061 (5)	0.0204 (6)	−0.0018 (5)
C10	0.0501 (7)	0.0405 (7)	0.0382 (6)	−0.0091 (5)	0.0211 (5)	−0.0002 (5)
C11	0.0533 (7)	0.0544 (8)	0.0502 (7)	−0.0131 (6)	0.0290 (6)	0.0035 (6)
C12	0.0442 (7)	0.0598 (8)	0.0527 (8)	−0.0078 (6)	0.0268 (6)	−0.0023 (6)
C13	0.0427 (6)	0.0479 (7)	0.0484 (7)	−0.0060 (5)	0.0202 (6)	−0.0031 (6)
C14	0.0494 (7)	0.0411 (7)	0.0506 (7)	−0.0103 (5)	0.0271 (6)	−0.0034 (5)
C15	0.0459 (6)	0.0403 (6)	0.0389 (6)	−0.0108 (5)	0.0224 (5)	−0.0048 (5)
C16	0.0566 (7)	0.0412 (7)	0.0552 (8)	−0.0116 (5)	0.0344 (6)	−0.0090 (5)
C17	0.0584 (9)	0.0547 (9)	0.0922 (13)	0.0011 (7)	0.0413 (9)	−0.0017 (8)
C18	0.0586 (8)	0.0602 (9)	0.0509 (8)	0.0047 (7)	0.0190 (7)	−0.0121 (7)
O1	0.0731 (7)	0.0412 (5)	0.0592 (6)	−0.0058 (4)	0.0407 (5)	0.0045 (4)
O2	0.0869 (8)	0.0406 (6)	0.0736 (7)	−0.0014 (5)	0.0413 (7)	0.0036 (5)

Geometric parameters (Å, º) top

C1—C2	1.375 (2)	C10—C11	1.3819 (19)
C1—C6	1.3941 (18)	C10—O1	1.3972 (16)
C1—H1	0.9300	C11—C12	1.369 (2)
C2—C3	1.374 (2)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.3871 (19)
C3—C4	1.375 (2)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.3914 (18)
C4—C5	1.396 (2)	C13—C17	1.500 (2)
C4—H4	0.9300	C14—C15	1.3844 (18)
C5—C6	1.4014 (18)	C14—H14	0.9300
C5—C18	1.495 (2)	C15—C16	1.5016 (17)
C6—C7	1.4655 (18)	C16—H16A	0.9700
C7—C8	1.3360 (18)	C16—H16B	0.9700
C7—H7	0.9300	C17—H17A	0.9600
C8—C9	1.4788 (18)	C17—H17B	0.9600
C8—C16	1.4981 (17)	C17—H17C	0.9600
C9—O2	1.2025 (16)	C18—H18A	0.9600
C9—O1	1.3615 (17)	C18—H18B	0.9600
C10—C15	1.3804 (16)	C18—H18C	0.9600

C2—C1—C6	121.40 (14)	C10—C11—H11	120.5
C2—C1—H1	119.3	C11—C12—C13	121.58 (13)
C6—C1—H1	119.3	C11—C12—H12	119.2
C3—C2—C1	119.64 (15)	C13—C12—H12	119.2
C3—C2—H2	120.2	C12—C13—C14	117.79 (13)
C1—C2—H2	120.2	C12—C13—C17	121.07 (13)
C2—C3—C4	119.89 (14)	C14—C13—C17	121.13 (12)
C2—C3—H3	120.1	C15—C14—C13	122.15 (12)
C4—C3—H3	120.1	C15—C14—H14	118.9
C3—C4—C5	121.73 (14)	C13—C14—H14	118.9
C3—C4—H4	119.1	C10—C15—C14	117.57 (12)
C5—C4—H4	119.1	C10—C15—C16	119.47 (12)
C4—C5—C6	118.14 (13)	C14—C15—C16	122.95 (11)
C4—C5—C18	120.06 (13)	C8—C16—C15	111.67 (10)
C6—C5—C18	121.79 (13)	C8—C16—H16A	109.3
C1—C6—C5	119.18 (12)	C15—C16—H16A	109.3
C1—C6—C7	121.02 (12)	C8—C16—H16B	109.3
C5—C6—C7	119.74 (12)	C15—C16—H16B	109.3
C8—C7—C6	127.45 (12)	H16A—C16—H16B	107.9
C8—C7—H7	116.3	C13—C17—H17A	109.5
C6—C7—H7	116.3	C13—C17—H17B	109.5
C7—C8—C9	116.20 (12)	H17A—C17—H17B	109.5
C7—C8—C16	126.09 (12)	C13—C17—H17C	109.5
C9—C8—C16	117.71 (11)	H17A—C17—H17C	109.5
O2—C9—O1	116.54 (12)	H17B—C17—H17C	109.5
O2—C9—C8	125.65 (13)	C5—C18—H18A	109.5
O1—C9—C8	117.80 (11)	C5—C18—H18B	109.5
C15—C10—C11	121.98 (13)	H18A—C18—H18B	109.5
C15—C10—O1	121.54 (12)	C5—C18—H18C	109.5
C11—C10—O1	116.40 (11)	H18A—C18—H18C	109.5
C12—C11—C10	118.93 (12)	H18B—C18—H18C	109.5
C12—C11—H11	120.5	C9—O1—C10	121.72 (10)

C6—C1—C2—C3	−0.3 (2)	O1—C10—C11—C12	176.16 (12)
C1—C2—C3—C4	−0.8 (2)	C10—C11—C12—C13	0.7 (2)
C2—C3—C4—C5	0.8 (2)	C11—C12—C13—C14	0.1 (2)
C3—C4—C5—C6	0.3 (2)	C11—C12—C13—C17	179.65 (14)
C3—C4—C5—C18	179.28 (13)	C12—C13—C14—C15	−0.8 (2)
C2—C1—C6—C5	1.4 (2)	C17—C13—C14—C15	179.56 (13)
C2—C1—C6—C7	178.65 (13)	C11—C10—C15—C14	−0.14 (19)
C4—C5—C6—C1	−1.40 (18)	O1—C10—C15—C14	−176.75 (11)
C18—C5—C6—C1	179.66 (12)	C11—C10—C15—C16	178.69 (12)
C4—C5—C6—C7	−178.68 (12)	O1—C10—C15—C16	2.07 (19)
C18—C5—C6—C7	2.38 (18)	C13—C14—C15—C10	0.9 (2)
C1—C6—C7—C8	42.3 (2)	C13—C14—C15—C16	−177.90 (12)
C5—C6—C7—C8	−140.44 (14)	C7—C8—C16—C15	144.14 (13)
C6—C7—C8—C9	−179.09 (12)	C9—C8—C16—C15	−35.18 (17)
C6—C7—C8—C16	1.6 (2)	C10—C15—C16—C8	23.76 (17)
C7—C8—C9—O2	21.8 (2)	C14—C15—C16—C8	−157.48 (12)
C16—C8—C9—O2	−158.81 (14)	O2—C9—O1—C10	−173.36 (12)
C7—C8—C9—O1	−157.79 (12)	C8—C9—O1—C10	6.27 (18)
C16—C8—C9—O1	21.60 (17)	C15—C10—O1—C9	−18.82 (19)
C15—C10—C11—C12	−0.6 (2)	C11—C10—O1—C9	164.39 (12)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1-C6 ring

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1ⁱ	0.93	2.53	3.437 (2)	167
C14—H14···Cgⁱⁱ	0.93	2.88	3.611 (2)	137
C18—H18A···Cgⁱⁱⁱ	0.96	2.74	3.490 (2)	136

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆O₂
M_r	264.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.1331 (2), 17.8838 (5), 9.6443 (3)
β (°)	118.056 (1)
V (Å³)	1390.14 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.21 × 0.18 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.983, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	17986, 4246, 2882
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.716

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.152, 1.00
No. of reflections	4246
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.17

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia (1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1-C6 ring

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1ⁱ	0.93	2.53	3.437 (2)	167
C14—H14···Cgⁱⁱ	0.93	2.88	3.611 (2)	137
C18—H18A···Cgⁱⁱⁱ	0.96	2.74	3.490 (2)	136

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

Footnotes

‡Additional correspondence author, e-mail: bhakthadoss@yahoo.com.

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

Brühlmann, C., Ooms, F., Carrupt, P.-A., Testa, B., Catto, M., Leonetti, F., Altomare, C. & Carotti, A. (2001). J. Med. Chem. 44, 3195–3198. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, K.-S. & Kim, S.-G. (2010). Acta Cryst. E66, o3104. Web of Science CSD CrossRef IUCr Journals 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
Iqbal, P. F., Bhat, A. R. & Azam, A. (2009). Eur. J. Med. Chem. 44, 2252–2259. Web of Science CrossRef PubMed CAS Google Scholar
Peng, Z.-Y., Liu, X.-Y., Yang, Y.-L., Xiang, K.-S. & Xiao, Z.-P. (2012). Acta Cryst. E68, o250. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rollinger, J. M., Hornick, A., Langer, T., Stuppner, H. & Prast, H. (2004). J. Med. Chem. 47, 6248–6254. Web of Science CrossRef PubMed CAS Google Scholar
Sharma, S. D., Rajor, H. K., Chopra, S. & Sharma, R. K. (2005). Biometals, 18, 143–154. Web of Science CrossRef PubMed CAS 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
Siddiqui, N., Arshad, M. F. & Khan, S. A. (2009). Acta Pol. Pharm. 66, 161–167. Web of Science PubMed CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vyas, K. B., Nimavat, K. S., Jani, G. R. & Hathi, M. V. (2009). Orbital, 1, 183–192. CAS Google Scholar