(2E)-1-(3-Bromo­phen­yl)-3-(6-meth­oxy-2-naphth­yl)prop-2-en-1-one

Harrison, W.T.A.; Mayekar, A.N.; Yathirajan, H.S.; Narayana, B.

doi:10.1107/S1600536810035117

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2552

doi:10.1107/S1600536810035117

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(2E)-1-(3-Bromophenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one

William T. A. Harrison,^a ^* A. N. Mayekar,^b,^c H. S. Yathirajan ^b and B. Narayana ^d

^aDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, ^cSeQuent Scientific Limited, New Mangalore 575 011, India, and ^dDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, India
^*Correspondence e-mail: w.harrison@abdn.ac.uk

(Received 9 August 2010; accepted 31 August 2010; online 11 September 2010)

In the title compound, C₂₀H₁₅BrO₂, the prop-2-en-1-one fragment is substantially twisted [C—C—C—O = 23.0 (11)°]. The dihedral angle between the benzene and naphthalene rings is 44.28 (13)°. The only possible directional interactions in the crystal are weak C—H⋯π contacts, which generate (001) sheets.

Related literature

For related structures, see: Yathirajan et al. (2007a ,b ); Jasinski et al. (2009 ). For background to the non-linear optical properties of chalcones, see: Sarojini et al. (2006 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₀H₁₅BrO₂
M_r = 367.23
Orthorhombic, P b c a
a = 14.0955 (14) Å
b = 6.1295 (6) Å
c = 36.119 (4) Å
V = 3120.6 (5) Å³
Z = 8
Mo Kα radiation
μ = 2.64 mm⁻¹
T = 120 K
0.11 × 0.09 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.760, T_max = 0.925
28579 measured reflections
3545 independent reflections
1719 reflections with I > 2σ(I)
R_int = 0.228

Refinement

R[F² > 2σ(F²)] = 0.082
wR(F²) = 0.163
S = 1.05
3545 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg2ⁱ	0.95	2.70	3.432 (6)	134
C7—H7⋯Cg2ⁱⁱ	0.95	2.80	3.520 (6)	134
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{3\over 2}}, z]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997), SCALEPACK and SORTAV (Blessing, 1995 ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035117/tk2699sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035117/tk2699Isup2.hkl

checkCIF report

Comment top

The title compound, (I), (Fig. 1), was prepared as part of our ongoing studies (Yathirajan et al., 2007a,b; Jasinski et al., 2009) of substituted phenyl/naphthyl chalcone derivatives as possible candidates for non-linear optical materials (Sarojini et al., 2006). However, (I) crystallizes in a centrosymmetric space group, thus its second-harmonic generation (SHG) response must be zero.

The prop-2-en-1-one (enone) fragment in (I) is substantially twisted, as indicated by the C11—C12—C13—O2 torsion angle of 23.0 (11)°. The dihedral angle between the aromatic ring systems is 44.28 (13)°. Equivalent data for related structures are as follows: (2E)-1-(2,4-dichlorophenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one (Yathirajan et al., 2007a): -10.9 (2) and 44.94 (4)°; (2E)-3-(6-methoxy-2-naphthyl)-1-phenylprop-2-en-1-one (Yathirajan et al., 2007b): -15.9 (4) and 14.9 (8)°; (2E)-1-(2-hydroxyphenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one (Jasinski et al., 2009): -14.9 (2) and 31.7 (3)°. Otherwise, the bond lengths for (I) fall within their expected ranges (Allen et al., 1987).

In the crystal of (I), the only possible directional interactions between molecules are weak C—H···π contacts in which the C3–C8 ring of the naphthyl moiety provides both the C—H donor groups and the aromatic acceptor surface (Table 1, Fig. 2). Together, these generate (001) sheets.

Related literature top

For related structures, see: Yathirajan et al. (2007a,b); Jasinski et al. (2009). For background to the non-linear optical properties of chalcones, see: Sarojini et al. (2006). For reference structural data, see: Allen et al. (1987).

Experimental top

To a thoroughly stirred solution of 6-methoxy-2-naphthaldehyde (1.86 g, 0.01 mol) and 3-bromoacetophenone (1.99 g, 0.01 mol) in 25 ml methanol, 5 ml of 40% KOH solution was added. The reaction mixture was stirred overnight and the solid separated was collected by filtration. The product obtained was recrystallized from methanol. Colourless slabs of (I) were grown by the slow evaporation of the ethylacetate solution (m.p. 427–429 K).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997), and SORTAV (Blessing, 1995); 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).

Figures top

	Fig. 1. View of the molecular structure of (I) showing 50% displacement ellipsoids (arbitrary spheres for the H atoms).
	Fig. 2. Partial packing diagram for (I) showing the possible weak C—H···π contacts. All H atoms except H4 and H7 omitted for clarity. Symmetry codes: (i) 1/2–x, y–1/2, z; (ii) 1–x, 1/2 + y, 1/2–z.

(2E)-1-(3-Bromophenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one top

Crystal data top

C₂₀H₁₅BrO₂	F(000) = 1488
M_r = 367.23	D_x = 1.563 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 55128 reflections
a = 14.0955 (14) Å	θ = 2.9–27.5°
b = 6.1295 (6) Å	µ = 2.64 mm⁻¹
c = 36.119 (4) Å	T = 120 K
V = 3120.6 (5) Å³	Slab, colourless
Z = 8	0.11 × 0.09 × 0.03 mm

Data collection top

Nonius KappaCCD diffractometer	3545 independent reflections
Radiation source: fine-focus sealed tube	1719 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.228
ω and ϕ scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −18→18
T_min = 0.760, T_max = 0.925	k = −7→7
28579 measured reflections	l = −46→46

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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0343P)² + 12.2862P] where P = (F_o² + 2F_c²)/3
3545 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

C₂₀H₁₅BrO₂	V = 3120.6 (5) Å³
M_r = 367.23	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.0955 (14) Å	µ = 2.64 mm⁻¹
b = 6.1295 (6) Å	T = 120 K
c = 36.119 (4) Å	0.11 × 0.09 × 0.03 mm

Data collection top

Nonius KappaCCD diffractometer	3545 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	1719 reflections with I > 2σ(I)
T_min = 0.760, T_max = 0.925	R_int = 0.228
28579 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0343P)² + 12.2862P] where P = (F_o² + 2F_c²)/3
3545 reflections	Δρ_max = 0.61 e Å⁻³
209 parameters	Δρ_min = −0.63 e Å⁻³

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
C1	0.3881 (4)	0.3963 (12)	0.14070 (18)	0.0269 (16)
C2	0.3536 (5)	0.2944 (11)	0.17160 (18)	0.0260 (16)
H2	0.3224	0.1576	0.1695	0.031*
C3	0.3647 (4)	0.3940 (11)	0.20683 (18)	0.0244 (15)
C4	0.3332 (4)	0.2939 (11)	0.23966 (18)	0.0247 (16)
H4	0.3057	0.1526	0.2384	0.030*
C5	0.3411 (4)	0.3933 (11)	0.27329 (17)	0.0257 (15)
H5	0.3192	0.3202	0.2949	0.031*
C6	0.3820 (4)	0.6074 (12)	0.27654 (18)	0.0226 (15)
C7	0.4144 (4)	0.7064 (11)	0.24441 (19)	0.0266 (17)
H7	0.4418	0.8477	0.2460	0.032*
C8	0.4083 (4)	0.6051 (12)	0.20954 (18)	0.0249 (16)
C9	0.4425 (5)	0.7045 (12)	0.1768 (2)	0.0316 (18)
H9	0.4724	0.8432	0.1782	0.038*
C10	0.4332 (4)	0.6034 (12)	0.14329 (19)	0.0290 (16)
H10	0.4569	0.6718	0.1216	0.035*
C11	0.3820 (4)	0.7262 (12)	0.31156 (18)	0.0262 (18)
H11	0.4035	0.8730	0.3107	0.031*
C12	0.3550 (5)	0.6518 (11)	0.34459 (18)	0.0290 (17)
H12	0.3356	0.5039	0.3468	0.035*
C13	0.3544 (5)	0.7926 (12)	0.3780 (2)	0.0305 (17)
C14	0.3642 (4)	0.6878 (12)	0.4150 (2)	0.0276 (17)
C15	0.3486 (5)	0.8158 (12)	0.44671 (19)	0.0312 (17)
H15	0.3274	0.9622	0.4442	0.037*
C16	0.3638 (5)	0.7308 (12)	0.4810 (2)	0.0313 (17)
C17	0.3927 (5)	0.5156 (12)	0.48559 (19)	0.0290 (18)
H17	0.4014	0.4555	0.5096	0.035*
C18	0.4085 (5)	0.3918 (13)	0.4543 (2)	0.0363 (18)
H18	0.4305	0.2461	0.4571	0.044*
C19	0.3934 (5)	0.4728 (12)	0.4191 (2)	0.035 (2)
H19	0.4029	0.3827	0.3981	0.042*
C20	0.3351 (5)	0.1184 (12)	0.10028 (19)	0.0400 (19)
H20A	0.3318	0.0822	0.0739	0.060*
H20B	0.2707	0.1298	0.1103	0.060*
H20C	0.3697	0.0036	0.1135	0.060*
O1	0.3827 (3)	0.3202 (8)	0.10487 (13)	0.0351 (13)
O2	0.3495 (4)	0.9934 (9)	0.37483 (13)	0.0361 (12)
Br1	0.34948 (6)	0.90763 (13)	0.52413 (2)	0.0403 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.024 (4)	0.033 (4)	0.024 (4)	0.007 (4)	−0.003 (3)	−0.002 (4)
C2	0.027 (4)	0.023 (4)	0.027 (4)	−0.005 (4)	−0.011 (4)	−0.001 (3)
C3	0.022 (4)	0.022 (4)	0.029 (4)	0.002 (4)	0.000 (3)	−0.003 (4)
C4	0.021 (4)	0.019 (4)	0.034 (4)	0.002 (3)	0.004 (3)	0.006 (3)
C5	0.022 (3)	0.031 (4)	0.024 (4)	−0.002 (4)	0.003 (3)	0.008 (4)
C6	0.014 (3)	0.023 (4)	0.030 (4)	−0.001 (3)	−0.002 (3)	−0.001 (4)
C7	0.013 (3)	0.029 (4)	0.038 (5)	−0.001 (3)	0.002 (3)	0.004 (4)
C8	0.018 (3)	0.031 (4)	0.026 (4)	0.005 (4)	−0.001 (3)	0.000 (4)
C9	0.027 (4)	0.034 (4)	0.034 (5)	0.002 (4)	0.003 (4)	0.003 (4)
C10	0.022 (4)	0.032 (4)	0.033 (4)	0.000 (4)	0.003 (3)	0.009 (4)
C11	0.019 (4)	0.028 (4)	0.031 (4)	0.001 (3)	0.000 (3)	−0.009 (4)
C12	0.024 (4)	0.031 (4)	0.032 (4)	−0.006 (4)	0.000 (4)	−0.009 (3)
C13	0.021 (4)	0.032 (5)	0.038 (4)	−0.001 (4)	0.011 (4)	−0.001 (4)
C14	0.016 (4)	0.033 (4)	0.034 (4)	−0.002 (3)	0.002 (3)	−0.004 (4)
C15	0.025 (4)	0.030 (4)	0.039 (4)	−0.004 (4)	0.002 (4)	−0.007 (4)
C16	0.028 (4)	0.034 (4)	0.032 (4)	0.003 (3)	0.003 (4)	−0.004 (4)
C17	0.027 (4)	0.034 (4)	0.026 (4)	−0.003 (3)	−0.001 (3)	0.002 (3)
C18	0.030 (4)	0.038 (5)	0.041 (5)	0.000 (4)	−0.005 (4)	−0.003 (5)
C19	0.023 (4)	0.040 (5)	0.042 (5)	−0.001 (3)	−0.011 (4)	−0.007 (4)
C20	0.059 (5)	0.033 (4)	0.029 (4)	−0.007 (4)	−0.005 (4)	−0.004 (4)
O1	0.045 (3)	0.035 (3)	0.026 (3)	−0.002 (2)	0.001 (2)	−0.001 (3)
O2	0.034 (3)	0.044 (3)	0.031 (3)	0.006 (3)	0.001 (3)	−0.002 (3)
Br1	0.0471 (4)	0.0440 (5)	0.0298 (4)	0.0048 (5)	0.0016 (4)	−0.0062 (4)

Geometric parameters (Å, º) top

C1—C2	1.369 (9)	C11—H11	0.9500
C1—O1	1.378 (8)	C12—C13	1.483 (9)
C1—C10	1.422 (9)	C12—H12	0.9500
C2—C3	1.420 (9)	C13—O2	1.238 (8)
C2—H2	0.9500	C13—C14	1.489 (10)
C3—C4	1.407 (9)	C14—C19	1.389 (9)
C3—C8	1.436 (9)	C14—C15	1.406 (9)
C4—C5	1.364 (9)	C15—C16	1.361 (9)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.439 (9)	C16—C17	1.391 (10)
C5—H5	0.9500	C16—Br1	1.909 (7)
C6—C7	1.387 (9)	C17—C18	1.379 (9)
C6—C11	1.459 (9)	C17—H17	0.9500
C7—C8	1.407 (9)	C18—C19	1.380 (10)
C7—H7	0.9500	C18—H18	0.9500
C8—C9	1.414 (9)	C19—H19	0.9500
C9—C10	1.366 (9)	C20—O1	1.418 (8)
C9—H9	0.9500	C20—H20A	0.9800
C10—H10	0.9500	C20—H20B	0.9800
C11—C12	1.333 (9)	C20—H20C	0.9800

C2—C1—O1	126.3 (6)	C6—C11—H11	116.4
C2—C1—C10	120.8 (6)	C11—C12—C13	122.0 (7)
O1—C1—C10	112.9 (6)	C11—C12—H12	119.0
C1—C2—C3	119.7 (6)	C13—C12—H12	119.0
C1—C2—H2	120.1	O2—C13—C12	120.3 (7)
C3—C2—H2	120.1	O2—C13—C14	121.1 (7)
C4—C3—C2	122.2 (6)	C12—C13—C14	118.6 (6)
C4—C3—C8	118.1 (6)	C19—C14—C15	119.2 (7)
C2—C3—C8	119.7 (6)	C19—C14—C13	122.2 (7)
C5—C4—C3	122.0 (6)	C15—C14—C13	118.5 (6)
C5—C4—H4	119.0	C16—C15—C14	120.2 (7)
C3—C4—H4	119.0	C16—C15—H15	119.9
C4—C5—C6	120.9 (6)	C14—C15—H15	119.9
C4—C5—H5	119.6	C15—C16—C17	121.2 (7)
C6—C5—H5	119.6	C15—C16—Br1	120.6 (5)
C7—C6—C5	117.6 (6)	C17—C16—Br1	118.2 (5)
C7—C6—C11	120.5 (6)	C18—C17—C16	118.1 (7)
C5—C6—C11	121.7 (6)	C18—C17—H17	120.9
C6—C7—C8	122.4 (6)	C16—C17—H17	120.9
C6—C7—H7	118.8	C17—C18—C19	122.1 (7)
C8—C7—H7	118.8	C17—C18—H18	119.0
C7—C8—C9	122.5 (7)	C19—C18—H18	119.0
C7—C8—C3	119.0 (6)	C18—C19—C14	119.1 (8)
C9—C8—C3	118.5 (6)	C18—C19—H19	120.4
C10—C9—C8	120.8 (7)	C14—C19—H19	120.4
C10—C9—H9	119.6	O1—C20—H20A	109.5
C8—C9—H9	119.6	O1—C20—H20B	109.5
C9—C10—C1	120.4 (7)	H20A—C20—H20B	109.5
C9—C10—H10	119.8	O1—C20—H20C	109.5
C1—C10—H10	119.8	H20A—C20—H20C	109.5
C12—C11—C6	127.2 (7)	H20B—C20—H20C	109.5
C12—C11—H11	116.4	C1—O1—C20	115.6 (6)

O1—C1—C2—C3	−180.0 (6)	C7—C6—C11—C12	−178.5 (7)
C10—C1—C2—C3	−1.4 (9)	C5—C6—C11—C12	7.2 (10)
C1—C2—C3—C4	−178.0 (6)	C6—C11—C12—C13	−177.3 (6)
C1—C2—C3—C8	2.7 (9)	C11—C12—C13—O2	23.0 (11)
C2—C3—C4—C5	−177.7 (6)	C11—C12—C13—C14	−154.4 (6)
C8—C3—C4—C5	1.6 (9)	O2—C13—C14—C19	−163.5 (7)
C3—C4—C5—C6	0.2 (10)	C12—C13—C14—C19	13.8 (10)
C4—C5—C6—C7	−1.1 (9)	O2—C13—C14—C15	12.6 (10)
C4—C5—C6—C11	173.4 (6)	C12—C13—C14—C15	−170.1 (6)
C5—C6—C7—C8	0.1 (9)	C19—C14—C15—C16	1.2 (10)
C11—C6—C7—C8	−174.5 (6)	C13—C14—C15—C16	−175.0 (6)
C6—C7—C8—C9	−179.1 (6)	C14—C15—C16—C17	−1.5 (10)
C6—C7—C8—C3	1.7 (10)	C14—C15—C16—Br1	176.6 (5)
C4—C3—C8—C7	−2.5 (9)	C15—C16—C17—C18	1.9 (10)
C2—C3—C8—C7	176.8 (6)	Br1—C16—C17—C18	−176.2 (5)
C4—C3—C8—C9	178.3 (6)	C16—C17—C18—C19	−2.2 (10)
C2—C3—C8—C9	−2.4 (9)	C17—C18—C19—C14	2.0 (10)
C7—C8—C9—C10	−178.3 (6)	C15—C14—C19—C18	−1.5 (10)
C3—C8—C9—C10	0.9 (10)	C13—C14—C19—C18	174.6 (6)
C8—C9—C10—C1	0.4 (10)	C2—C1—O1—C20	1.2 (9)
C2—C1—C10—C9	−0.2 (10)	C10—C1—O1—C20	−177.5 (6)
O1—C1—C10—C9	178.6 (6)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg2ⁱ	0.95	2.70	3.432 (6)	134
C7—H7···Cg2ⁱⁱ	0.95	2.80	3.520 (6)	134

Symmetry codes: (i) −x+1/2, y−3/2, z; (ii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅BrO₂
M_r	367.23
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	120
a, b, c (Å)	14.0955 (14), 6.1295 (6), 36.119 (4)
V (Å³)	3120.6 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.64
Crystal size (mm)	0.11 × 0.09 × 0.03

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.760, 0.925
No. of measured, independent and observed [I > 2σ(I)] reflections	28579, 3545, 1719
R_int	0.228
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.163, 1.05
No. of reflections	3545
No. of parameters	209
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0343P)² + 12.2862P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.63

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), and SORTAV (Blessing, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg2ⁱ	0.95	2.70	3.432 (6)	134
C7—H7···Cg2ⁱⁱ	0.95	2.80	3.520 (6)	134

Symmetry codes: (i) −x+1/2, y−3/2, z; (ii) −x+1, y+1/2, −z+1/2.

Acknowledgements

ANM thanks the University of Mysore for providing research facilities. HSY thanks the University of Mysore for sanctioning sabbatical leave.

References

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