9-(4-Meth­oxy­phen­yl)anthracene

Silambarasan, V.; Srinivasan, T.; Sivasakthikumaran, R.; Mohanakrishnan, A.K.; Velmurugan, D.

doi:10.1107/S1600536812047149

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3410

doi:10.1107/S1600536812047149

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9-(4-Methoxyphenyl)anthracene

V. Silambarasan,^a T. Srinivasan,^a R. Sivasakthikumaran,^b A. K. Mohanakrishnan ^b and D. Velmurugan ^a ^*

^aCAS in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai-25, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai-25, India
^*Correspondence e-mail: shirai2011@gmail.com

(Received 22 October 2012; accepted 16 November 2012; online 24 November 2012)

In the title compound, C₂₁H₁₆O, the dihedral angle between the anthracene ring system and the benzene ring is 74.3 (5)°. The anthracene ring system is essentially planar (r.m.s. deviation = 0.0257 Å) and the methoxy group lies in the plane of the benzene ring [C1—O1—C2—C7 torsion angle = 0.5 (2)°]. The crystal structure features π–π [centroid–centroid distance = 3.9487 (12) Å] and C–H⋯π interactions, forming a sheet running along the a-axis direction.

Related literature

For applications of anthracene, see: Bae et al. (2010 ); Debbab et al. (2012 ). For a related structure, see: Wang et al. (2008 ).

Experimental

Crystal data

C₂₁H₁₆O
M_r = 284.34
Monoclinic, P 2₁ /c
a = 13.5539 (5) Å
b = 15.0626 (5) Å
c = 7.6130 (2) Å
β = 99.219 (2)°
V = 1534.17 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.981, T_max = 0.985
14917 measured reflections
3806 independent reflections
2317 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.130
S = 1.02
3806 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg4 are the centroids of the C2–C7 and C16–C21 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cg4ⁱ	0.93	2.77	3.566 (2)	145
C11—H11⋯Cg1ⁱⁱ	0.93	2.87	3.724 (2)	154
C19—H19⋯Cg1ⁱⁱⁱ	0.93	2.94	3.772 (2)	150
C21—H21⋯Cg4^iv	0.93	2.88	3.711 (2)	150
Symmetry codes: (i) x, y, z-1; (ii) -x+1, -y, -z; (iii) -x+2, -y, -z+1; (iv) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812047149/pv2599sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812047149/pv2599Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812047149/pv2599Isup3.cml

checkCIF report

Comment top

Anthracene is a solid polycyclic aromatic hydrocarbon consisting of three fused benzene rings. Its derivatives possess antimicrobial activity (Debbab et al., 2012). It is used in the production of dyes and organic semiconductors (Bae et al., 2010). In order to obtain detailed information on molecular conformations in the solid state, an X-ray crystallographic study of the title compound was carried out.

The anthracene ring system in the title molecule (Fig. 1) is essentially planar (rmsd = 0.0257 Å) and the methoxy group lies in the plane of the benzene ring with the torsion angle C1—O1—C2—C7 = 0.5 (2)°. The dihedral angle between the mean-planes of the anthracene and benzene rings is 74.3 (5)° showing that both the ring systems are almost perpendicular to each other. The bond lengths and angles in the title compound are comparable to those observed in a closely related compound (Wang et al., 2008).

The π···π electron interaction is observed between the rings (C9—C14) [at x, y, z] and (C9—C14) [at 1 - x, - y, 1 - z] with the centroid-centroid distance 3.9487 (12) Å. In addition, the crystal packing is stabilized by C–H···π (Table. 1) types of interaction.

Related literature top

For applications of anthracene, see: Bae et al. (2010); Debbab et al. (2012). For a related structure, see: Wang et al. (2008).

Experimental top

(4-Methoxyphenyl)(2-(phenyl(pivaloyloxy)methyl)phenyl)methyl)pivalate (0.5 g, 0.94 mmol) upon interaction with ZnBr₂ (0.02 g, 0.13 mmol) followed by removal of solvent and column chromatographic purification (silica gel; hexane-ethyl acetate, 99:1) led to the isolation of product as a pale yellow solid (0.32 g, 87%). The compound was recrystalized from chloroform. Single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a solution of the title compound in acetone at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); 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 30% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the π···π and C—-H···π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity.

9-(4-Methoxyphenyl)anthracene top

Crystal data top

C₂₁H₁₆O	F(000) = 600
M_r = 284.34	D_x = 1.231 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3806 reflections
a = 13.5539 (5) Å	θ = 2.0–28.3°
b = 15.0626 (5) Å	µ = 0.07 mm⁻¹
c = 7.6130 (2) Å	T = 293 K
β = 99.219 (2)°	Block, colourless
V = 1534.17 (9) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII area-detector diffractometer	3806 independent reflections
Radiation source: fine-focus sealed tube	2317 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω and ϕ scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −18→16
T_min = 0.981, T_max = 0.985	k = −19→19
14917 measured reflections	l = −10→10

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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.0556P)² + 0.1555P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3806 reflections	Δρ_max = 0.14 e Å⁻³
201 parameters	Δρ_min = −0.12 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (2)

Crystal data top

C₂₁H₁₆O	V = 1534.17 (9) Å³
M_r = 284.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.5539 (5) Å	µ = 0.07 mm⁻¹
b = 15.0626 (5) Å	T = 293 K
c = 7.6130 (2) Å	0.20 × 0.20 × 0.20 mm
β = 99.219 (2)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	3806 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2317 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.985	R_int = 0.033
14917 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.02	Δρ_max = 0.14 e Å⁻³
3806 reflections	Δρ_min = −0.12 e Å⁻³
201 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
O1	0.84535 (8)	−0.16715 (6)	−0.12133 (14)	0.0625 (3)
C5	0.75001 (9)	0.00335 (9)	0.24854 (16)	0.0444 (3)
C8	0.71622 (11)	0.06367 (9)	0.38283 (16)	0.0469 (3)
C4	0.73498 (10)	−0.08803 (9)	0.25059 (19)	0.0513 (4)
H4	0.7022	−0.1127	0.3373	0.062*
C6	0.79836 (11)	0.03687 (9)	0.11597 (18)	0.0543 (4)
H6	0.8091	0.0978	0.1112	0.065*
C2	0.81595 (9)	−0.10761 (9)	−0.00379 (17)	0.0471 (3)
C17	0.78712 (11)	0.10166 (9)	0.51685 (17)	0.0484 (3)
C9	0.61419 (11)	0.08466 (10)	0.37219 (18)	0.0542 (4)
C3	0.76772 (11)	−0.14246 (9)	0.12656 (19)	0.0526 (4)
H3	0.7572	−0.2034	0.1309	0.063*
C16	0.75482 (13)	0.16124 (9)	0.64257 (18)	0.0571 (4)
C18	0.89164 (11)	0.08456 (10)	0.53287 (18)	0.0553 (4)
H18	0.9144	0.0464	0.4521	0.066*
C14	0.58323 (13)	0.14597 (11)	0.4959 (2)	0.0633 (4)
C7	0.83127 (11)	−0.01703 (9)	−0.00955 (18)	0.0535 (4)
H7	0.8635	0.0074	−0.0972	0.064*
C19	0.95862 (14)	0.12230 (11)	0.6623 (2)	0.0687 (5)
H19	1.0264	0.1101	0.6690	0.082*
C15	0.65393 (14)	0.18180 (10)	0.6282 (2)	0.0681 (5)
H15	0.6333	0.2208	0.7099	0.082*
C21	0.82821 (16)	0.19878 (11)	0.7773 (2)	0.0730 (5)
H21	0.8080	0.2371	0.8605	0.088*
C10	0.53910 (12)	0.04832 (12)	0.2391 (2)	0.0710 (5)
H10	0.5573	0.0077	0.1581	0.085*
C20	0.92599 (16)	0.18010 (12)	0.7871 (2)	0.0772 (5)
H20	0.9723	0.2054	0.8765	0.093*
C1	0.89552 (14)	−0.13330 (12)	−0.2567 (2)	0.0788 (5)
H1A	0.8533	−0.0912	−0.3275	0.118*
H1B	0.9110	−0.1812	−0.3309	0.118*
H1C	0.9562	−0.1046	−0.2035	0.118*
C13	0.47972 (16)	0.16896 (14)	0.4771 (3)	0.0847 (6)
H13	0.4587	0.2095	0.5555	0.102*
C11	0.44201 (14)	0.07163 (15)	0.2281 (3)	0.0893 (6)
H11	0.3945	0.0468	0.1402	0.107*
C12	0.41231 (16)	0.13311 (17)	0.3484 (3)	0.0960 (7)
H12	0.3454	0.1491	0.3386	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0721 (7)	0.0500 (6)	0.0713 (7)	0.0036 (5)	0.0293 (6)	−0.0138 (5)
C5	0.0457 (7)	0.0464 (7)	0.0423 (6)	0.0033 (6)	0.0101 (6)	−0.0003 (6)
C8	0.0587 (9)	0.0420 (7)	0.0433 (7)	0.0043 (6)	0.0183 (6)	0.0026 (6)
C4	0.0539 (8)	0.0488 (8)	0.0546 (8)	−0.0021 (6)	0.0190 (7)	0.0041 (6)
C6	0.0739 (10)	0.0397 (7)	0.0537 (8)	−0.0032 (7)	0.0235 (7)	−0.0027 (6)
C2	0.0444 (7)	0.0456 (7)	0.0526 (7)	0.0043 (6)	0.0112 (6)	−0.0073 (6)
C17	0.0664 (9)	0.0384 (7)	0.0439 (7)	−0.0020 (6)	0.0198 (6)	0.0027 (6)
C9	0.0628 (9)	0.0552 (9)	0.0485 (7)	0.0108 (7)	0.0207 (7)	0.0060 (7)
C3	0.0572 (9)	0.0384 (7)	0.0645 (9)	−0.0013 (6)	0.0169 (7)	−0.0005 (6)
C16	0.0865 (11)	0.0409 (7)	0.0494 (8)	−0.0037 (7)	0.0269 (8)	−0.0005 (6)
C18	0.0656 (10)	0.0521 (8)	0.0504 (8)	−0.0068 (7)	0.0163 (7)	−0.0022 (7)
C14	0.0776 (11)	0.0613 (10)	0.0580 (9)	0.0177 (8)	0.0322 (8)	0.0073 (8)
C7	0.0692 (10)	0.0459 (8)	0.0507 (7)	−0.0032 (7)	0.0258 (7)	−0.0015 (6)
C19	0.0736 (11)	0.0719 (11)	0.0605 (9)	−0.0202 (9)	0.0111 (8)	−0.0043 (8)
C15	0.1015 (14)	0.0520 (9)	0.0599 (9)	0.0122 (9)	0.0405 (9)	−0.0029 (7)
C21	0.1192 (16)	0.0489 (9)	0.0561 (9)	−0.0182 (10)	0.0303 (10)	−0.0120 (7)
C10	0.0626 (10)	0.0904 (13)	0.0613 (9)	0.0193 (9)	0.0136 (8)	−0.0032 (9)
C20	0.1028 (15)	0.0692 (11)	0.0601 (10)	−0.0349 (11)	0.0147 (10)	−0.0097 (8)
C1	0.0935 (13)	0.0728 (12)	0.0811 (11)	−0.0002 (10)	0.0480 (10)	−0.0192 (10)
C13	0.0924 (14)	0.0910 (14)	0.0807 (12)	0.0338 (11)	0.0441 (11)	0.0065 (11)
C11	0.0623 (11)	0.1274 (18)	0.0782 (11)	0.0241 (11)	0.0109 (9)	−0.0017 (12)
C12	0.0735 (13)	0.1313 (19)	0.0882 (14)	0.0398 (13)	0.0287 (12)	0.0091 (14)

Geometric parameters (Å, º) top

O1—C2	1.3704 (15)	C18—H18	0.9300
O1—C1	1.4176 (18)	C14—C15	1.384 (2)
C5—C6	1.3838 (17)	C14—C13	1.430 (3)
C5—C4	1.3919 (18)	C7—H7	0.9300
C5—C8	1.4935 (17)	C19—C20	1.411 (2)
C8—C17	1.4063 (19)	C19—H19	0.9300
C8—C9	1.408 (2)	C15—H15	0.9300
C4—C3	1.3766 (19)	C21—C20	1.345 (3)
C4—H4	0.9300	C21—H21	0.9300
C6—C7	1.3813 (18)	C10—C11	1.352 (2)
C6—H6	0.9300	C10—H10	0.9300
C2—C3	1.3768 (18)	C20—H20	0.9300
C2—C7	1.3818 (19)	C1—H1A	0.9600
C17—C18	1.426 (2)	C1—H1B	0.9600
C17—C16	1.4309 (19)	C1—H1C	0.9600
C9—C10	1.425 (2)	C13—C12	1.341 (3)
C9—C14	1.429 (2)	C13—H13	0.9300
C3—H3	0.9300	C11—C12	1.406 (3)
C16—C15	1.389 (2)	C11—H11	0.9300
C16—C21	1.426 (2)	C12—H12	0.9300
C18—C19	1.353 (2)

C2—O1—C1	117.58 (11)	C6—C7—C2	119.44 (12)
C6—C5—C4	117.14 (12)	C6—C7—H7	120.3
C6—C5—C8	120.68 (12)	C2—C7—H7	120.3
C4—C5—C8	122.17 (11)	C18—C19—C20	120.22 (17)
C17—C8—C9	120.07 (12)	C18—C19—H19	119.9
C17—C8—C5	119.69 (12)	C20—C19—H19	119.9
C9—C8—C5	120.21 (13)	C14—C15—C16	121.90 (14)
C3—C4—C5	121.16 (12)	C14—C15—H15	119.1
C3—C4—H4	119.4	C16—C15—H15	119.1
C5—C4—H4	119.4	C20—C21—C16	121.62 (16)
C7—C6—C5	122.23 (13)	C20—C21—H21	119.2
C7—C6—H6	118.9	C16—C21—H21	119.2
C5—C6—H6	118.9	C11—C10—C9	121.45 (17)
O1—C2—C3	116.26 (12)	C11—C10—H10	119.3
O1—C2—C7	124.36 (12)	C9—C10—H10	119.3
C3—C2—C7	119.38 (12)	C21—C20—C19	120.27 (16)
C8—C17—C18	122.87 (12)	C21—C20—H20	119.9
C8—C17—C16	119.58 (13)	C19—C20—H20	119.9
C18—C17—C16	117.54 (13)	O1—C1—H1A	109.5
C8—C9—C10	122.52 (13)	O1—C1—H1B	109.5
C8—C9—C14	119.77 (14)	H1A—C1—H1B	109.5
C10—C9—C14	117.70 (14)	O1—C1—H1C	109.5
C4—C3—C2	120.65 (13)	H1A—C1—H1C	109.5
C4—C3—H3	119.7	H1B—C1—H1C	109.5
C2—C3—H3	119.7	C12—C13—C14	121.20 (17)
C15—C16—C21	122.17 (15)	C12—C13—H13	119.4
C15—C16—C17	119.34 (15)	C14—C13—H13	119.4
C21—C16—C17	118.48 (15)	C10—C11—C12	120.5 (2)
C19—C18—C17	121.86 (14)	C10—C11—H11	119.7
C19—C18—H18	119.1	C12—C11—H11	119.7
C17—C18—H18	119.1	C13—C12—C11	120.56 (18)
C15—C14—C9	119.31 (14)	C13—C12—H12	119.7
C15—C14—C13	122.16 (16)	C11—C12—H12	119.7
C9—C14—C13	118.53 (17)

C6—C5—C8—C17	−72.83 (17)	C8—C17—C18—C19	179.58 (13)
C4—C5—C8—C17	106.98 (15)	C16—C17—C18—C19	0.5 (2)
C6—C5—C8—C9	105.19 (16)	C8—C9—C14—C15	−2.0 (2)
C4—C5—C8—C9	−74.99 (17)	C10—C9—C14—C15	179.23 (14)
C6—C5—C4—C3	0.5 (2)	C8—C9—C14—C13	177.33 (14)
C8—C5—C4—C3	−179.30 (13)	C10—C9—C14—C13	−1.4 (2)
C4—C5—C6—C7	−0.3 (2)	C5—C6—C7—C2	−0.1 (2)
C8—C5—C6—C7	179.51 (13)	O1—C2—C7—C6	179.96 (13)
C1—O1—C2—C3	−179.79 (13)	C3—C2—C7—C6	0.3 (2)
C1—O1—C2—C7	0.5 (2)	C17—C18—C19—C20	0.3 (2)
C9—C8—C17—C18	−178.74 (12)	C9—C14—C15—C16	1.3 (2)
C5—C8—C17—C18	−0.71 (19)	C13—C14—C15—C16	−178.05 (15)
C9—C8—C17—C16	0.35 (19)	C21—C16—C15—C14	179.21 (14)
C5—C8—C17—C16	178.38 (11)	C17—C16—C15—C14	0.3 (2)
C17—C8—C9—C10	179.89 (13)	C15—C16—C21—C20	−178.28 (15)
C5—C8—C9—C10	1.9 (2)	C17—C16—C21—C20	0.7 (2)
C17—C8—C9—C14	1.2 (2)	C8—C9—C10—C11	−177.86 (16)
C5—C8—C9—C14	−176.82 (12)	C14—C9—C10—C11	0.9 (2)
C5—C4—C3—C2	−0.3 (2)	C16—C21—C20—C19	0.1 (3)
O1—C2—C3—C4	−179.78 (13)	C18—C19—C20—C21	−0.6 (2)
C7—C2—C3—C4	−0.1 (2)	C15—C14—C13—C12	−179.66 (18)
C8—C17—C16—C15	−1.1 (2)	C9—C14—C13—C12	1.0 (3)
C18—C17—C16—C15	178.03 (13)	C9—C10—C11—C12	0.2 (3)
C8—C17—C16—C21	179.92 (12)	C14—C13—C12—C11	0.0 (3)
C18—C17—C16—C21	−0.94 (19)	C10—C11—C12—C13	−0.6 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg4 are the centroids of the C2–C7 and C16–C21 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg4ⁱ	0.93	2.77	3.566 (2)	145
C11—H11···Cg1ⁱⁱ	0.93	2.87	3.724 (2)	154
C19—H19···Cg1ⁱⁱⁱ	0.93	2.94	3.772 (2)	150
C21—H21···Cg4^iv	0.93	2.88	3.711 (2)	150

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆O
M_r	284.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.5539 (5), 15.0626 (5), 7.6130 (2)
β (°)	99.219 (2)
V (Å³)	1534.17 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.981, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	14917, 3806, 2317
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.130, 1.02
No. of reflections	3806
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.12

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg4 are the centroids of the C2–C7 and C16–C21 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg4ⁱ	0.93	2.77	3.566 (2)	145
C11—H11···Cg1ⁱⁱ	0.93	2.87	3.724 (2)	154
C19—H19···Cg1ⁱⁱⁱ	0.93	2.94	3.772 (2)	150
C21—H21···Cg4^iv	0.93	2.88	3.711 (2)	150

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

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. VS and DV also thank the UGC SAP for financial support.

References

Bae, S. Y., Jung, K. H., Hoang, M. H., Kim, K. H., Lee, T. W., Cho, M. J., Jin, J., Lee, D. H., Chung, D. S., Park, C. E. & Choi, D. H. (2010). Synth. Met. 160, 1022–1029. Web of Science CrossRef CAS Google Scholar
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Debbab, A., Aly, A. H., Edrada-Ebel, R., Wray, V., Pretsch, A., Pescitelli, G., Kurtan, T. & Proksch, P. (2012). Eur. J. Org. Chem. pp. 1351–1359. Web of Science CrossRef Google Scholar
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Volume 68| Part 12| December 2012| Page o3410

doi:10.1107/S1600536812047149

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