(2-Benzoyl­phen­yl)(naphthalen-1-yl)methanone

Ganesh, G.; Sivasakthikumaran, R.; Govindan, E.; Krishnan, A.K.M.; SubbiahPandi, A.

doi:10.1107/S1600536812039098

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o3012

https://doi.org/10.1107/S1600536812039098

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(2-Benzoylphenyl)(naphthalen-1-yl)methanone

G. Ganesh,^a R. Sivasakthikumaran,^b E. Govindan,^c A. K. Mohana Krishnan ^b and A. SubbiahPandi ^c ^*

^aDepartment of Physics, S.M.K. Fomra Institute of Technology, Thaiyur, Chennai 603 103, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
^*Correspondence e-mail: a_sp59@yahoo.in

(Received 31 August 2012; accepted 12 September 2012; online 26 September 2012)

In the title compound, C₂₄H₁₆O₂, the naphthalene ring system makes dihedral angles of 78.5 (6) and 65.5 (7)° with the terminal and central benzene rings, respectively. The dihedral angle between the benzene rings is 74.5 (8)°. In the crystal, neighbouring molecules are interlinked through two C—H⋯π interactions, which construct a two-dimensional supramolecular framework extending infinitely along (010).

Related literature

For the biological activity of naphthalene derivatives, see: Wiltz et al. (1998 ); Wright et al. (2000 ); Varma et al. (1994 ). For a related structure, see: Xia (2010 ).

Experimental

Crystal data

C₂₄H₁₆O₂
M_r = 336.37
Monoclinic, P 2₁ /n
a = 10.4105 (3) Å
b = 9.6218 (3) Å
c = 17.8497 (5) Å
β = 106.113 (2)°
V = 1717.73 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.980, T_max = 0.985
18980 measured reflections
4081 independent reflections
2906 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.135
S = 1.01
4081 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cg1ⁱ	0.93	2.71	3.618 (19)	163
C20—H20⋯Cg2ⁱⁱ	0.93	2.85	3.67 (3)	141
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

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, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812039098/bt6830sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039098/bt6830Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812039098/bt6830Isup3.cml

checkCIF report

Comment top

Naphthalene derivatives have manifested applications in many fields, for example, as a colorant, explosive, disinfectant, insecticide and plant hormone auxin. Naphthalene is believed to play a role in the chemical defence against biological enemies (Wiltz et al., 1998; Wright et al., 2000). It may be produced by metabolic processes in termites or by associated microorganisms which inhabit, e.g., the termite guts (Varma et al., 1994).

Bond lengths and bond angles of the title compound are comparable with the related structure (Xia, 2010). The napthyl ring C15—C24 system makes dihedral angles of 78.5 (6)° and 65.5 (7)°, with the phenyl rings C1—C6 and the C8—C13 respectively.

The C–H···π interaction C11–H11—Cg1i (Cg1 : C1–C6) [symmetry code : (i) x-1/2, -y-1/2, z-1/2] links the adjacent title moleculesto generate an extended one dimensional supramolecular network along [104] direction. Parallely stacked [104] network are further linked through C20–H20···Cg2ii (Cg2 : C8–C13) [symmetry code : (i) x-1/2, -y-1/2, z-3/2] interaction to form a two dimensional supramolecular sheet extending parallel to the (010) plane.

Related literature top

For the biological activity of naphthalene derivatives, see: Wiltz et al. (1998); Wright et al. (2000); Varma et al. (1994). For a related structure, see: Xia (2010).

Experimental top

To a stirred suspension of benzo[c]furan (2.38 g, 7.437 mmol) in dry THF (20 ml), lead tetraacetate (3.2 g, 7.437 mmol) was added and refluxed at 50°C for half an hour. The reaction mixture was then poured into water (200 ml) and extracted with ethyl acetate (2 x 20 ml), washed with brine solution and dried (Na₂SO₄). The removal of solvent in vacuo followed by crystallization from methanol afforded the title compound as a colorless solid. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in methanol at room temperature.

Structure description top

For the biological activity of naphthalene derivatives, see: Wiltz et al. (1998); Wright et al. (2000); Varma et al. (1994). For a related structure, see: Xia (2010).

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, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The structure of showing the atom-numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.

(2-Benzoylphenyl)(naphthalen-1-yl)methanone top

Crystal data top

C₂₄H₁₆O₂	F(000) = 704
M_r = 336.37	D_x = 1.301 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4106 reflections
a = 10.4105 (3) Å	θ = 2.1–27.9°
b = 9.6218 (3) Å	µ = 0.08 mm⁻¹
c = 17.8497 (5) Å	T = 293 K
β = 106.113 (2)°	Block, white crystalline
V = 1717.73 (9) Å³	0.25 × 0.22 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	4081 independent reflections
Radiation source: fine-focus sealed tube	2906 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω and φ scans	θ_max = 27.9°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.980, T_max = 0.985	k = −9→12
18980 measured reflections	l = −23→22

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0682P)² + 0.3208P] where P = (F_o² + 2F_c²)/3
4081 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₄H₁₆O₂	V = 1717.73 (9) Å³
M_r = 336.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.4105 (3) Å	µ = 0.08 mm⁻¹
b = 9.6218 (3) Å	T = 293 K
c = 17.8497 (5) Å	0.25 × 0.22 × 0.19 mm
β = 106.113 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4081 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2906 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.985	R_int = 0.024
18980 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.01	Δρ_max = 0.22 e Å⁻³
4081 reflections	Δρ_min = −0.17 e Å⁻³
235 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
C1	−0.12964 (14)	0.43758 (18)	0.19247 (9)	0.0514 (4)
H1	−0.1978	0.4398	0.2168	0.062*
C2	−0.11530 (16)	0.54645 (18)	0.14567 (10)	0.0577 (4)
H2	−0.1746	0.6209	0.1379	0.069*
C3	−0.01362 (17)	0.54578 (18)	0.11029 (10)	0.0572 (4)
H3	−0.0030	0.6205	0.0795	0.069*
C4	0.07240 (15)	0.43421 (16)	0.12060 (9)	0.0501 (4)
H4	0.1413	0.4341	0.0967	0.060*
C5	0.05740 (13)	0.32213 (15)	0.16614 (8)	0.0410 (3)
C6	−0.04434 (13)	0.32506 (15)	0.20384 (8)	0.0417 (3)
C7	−0.06077 (13)	0.21477 (16)	0.25979 (8)	0.0451 (3)
C8	0.04444 (13)	0.20243 (14)	0.33523 (8)	0.0404 (3)
C9	0.14254 (15)	0.30231 (16)	0.35969 (8)	0.0482 (3)
H9	0.1457	0.3780	0.3278	0.058*
C10	0.23568 (17)	0.28980 (18)	0.43124 (10)	0.0598 (4)
H10	0.3014	0.3574	0.4475	0.072*
C11	0.23221 (18)	0.1786 (2)	0.47854 (10)	0.0635 (5)
H11	0.2953	0.1708	0.5268	0.076*
C12	0.13550 (18)	0.0788 (2)	0.45457 (10)	0.0641 (5)
H12	0.1337	0.0028	0.4864	0.077*
C13	0.04130 (16)	0.09075 (17)	0.38380 (9)	0.0534 (4)
H13	−0.0250	0.0236	0.3683	0.064*
C14	0.14196 (13)	0.19692 (15)	0.17171 (8)	0.0423 (3)
C15	0.26477 (13)	0.20331 (15)	0.14345 (9)	0.0453 (3)
C16	0.25771 (14)	0.16839 (14)	0.06570 (9)	0.0452 (3)
C17	0.13610 (17)	0.13546 (16)	0.00976 (9)	0.0524 (4)
H17	0.0561	0.1393	0.0233	0.063*
C18	0.1356 (2)	0.09810 (19)	−0.06394 (10)	0.0701 (5)
H18	0.0556	0.0751	−0.1004	0.084*
C19	0.2565 (3)	0.0944 (2)	−0.08489 (13)	0.0841 (7)
H19	0.2556	0.0689	−0.1353	0.101*
C20	0.3734 (3)	0.1272 (2)	−0.03286 (14)	0.0783 (6)
H20	0.4520	0.1247	−0.0480	0.094*
C21	0.37831 (17)	0.16475 (16)	0.04334 (11)	0.0579 (4)
C22	0.49996 (17)	0.1967 (2)	0.10048 (15)	0.0723 (6)
H22	0.5797	0.1944	0.0867	0.087*
C23	0.50251 (17)	0.2301 (2)	0.17366 (14)	0.0743 (6)
H23	0.5835	0.2503	0.2099	0.089*
C24	0.38446 (16)	0.2346 (2)	0.19557 (11)	0.0646 (5)
H24	0.3870	0.2592	0.2463	0.078*
O1	−0.16245 (11)	0.14676 (16)	0.24595 (7)	0.0731 (4)
O2	0.11301 (12)	0.08900 (12)	0.19794 (7)	0.0604 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0423 (7)	0.0617 (10)	0.0521 (8)	0.0068 (7)	0.0164 (6)	−0.0069 (7)
C2	0.0572 (9)	0.0518 (10)	0.0615 (9)	0.0156 (7)	0.0124 (7)	−0.0009 (7)
C3	0.0655 (10)	0.0477 (9)	0.0583 (9)	0.0072 (7)	0.0172 (8)	0.0105 (7)
C4	0.0507 (8)	0.0525 (9)	0.0517 (8)	0.0047 (7)	0.0218 (7)	0.0079 (7)
C5	0.0373 (6)	0.0465 (8)	0.0399 (7)	0.0021 (6)	0.0120 (5)	0.0020 (6)
C6	0.0360 (6)	0.0502 (8)	0.0388 (7)	−0.0014 (6)	0.0103 (5)	−0.0032 (6)
C7	0.0365 (6)	0.0554 (9)	0.0476 (8)	−0.0056 (6)	0.0185 (6)	−0.0028 (6)
C8	0.0412 (7)	0.0426 (8)	0.0425 (7)	−0.0005 (6)	0.0200 (6)	−0.0029 (6)
C9	0.0515 (8)	0.0450 (8)	0.0476 (8)	−0.0047 (6)	0.0131 (6)	0.0007 (6)
C10	0.0584 (9)	0.0552 (10)	0.0583 (9)	−0.0065 (8)	0.0038 (7)	−0.0067 (8)
C11	0.0658 (10)	0.0691 (12)	0.0497 (9)	0.0113 (9)	0.0062 (8)	0.0034 (8)
C12	0.0744 (11)	0.0610 (11)	0.0599 (10)	0.0090 (9)	0.0238 (8)	0.0186 (8)
C13	0.0558 (8)	0.0488 (9)	0.0608 (9)	−0.0050 (7)	0.0246 (7)	0.0036 (7)
C14	0.0434 (7)	0.0462 (8)	0.0394 (7)	0.0016 (6)	0.0153 (6)	0.0020 (6)
C15	0.0395 (7)	0.0442 (8)	0.0551 (8)	0.0067 (6)	0.0178 (6)	0.0075 (6)
C16	0.0506 (8)	0.0354 (7)	0.0574 (8)	0.0096 (6)	0.0281 (7)	0.0095 (6)
C17	0.0641 (9)	0.0451 (8)	0.0517 (8)	0.0049 (7)	0.0221 (7)	0.0061 (7)
C18	0.1059 (15)	0.0519 (10)	0.0538 (9)	0.0014 (10)	0.0243 (10)	0.0047 (8)
C19	0.149 (2)	0.0582 (12)	0.0668 (12)	0.0200 (13)	0.0655 (14)	0.0093 (9)
C20	0.1069 (16)	0.0585 (12)	0.0952 (15)	0.0211 (11)	0.0707 (14)	0.0163 (10)
C21	0.0665 (10)	0.0403 (8)	0.0830 (11)	0.0154 (7)	0.0474 (9)	0.0164 (8)
C22	0.0474 (9)	0.0612 (11)	0.1210 (17)	0.0115 (8)	0.0445 (10)	0.0251 (11)
C23	0.0413 (8)	0.0803 (14)	0.0990 (15)	0.0006 (9)	0.0156 (9)	0.0176 (11)
C24	0.0485 (8)	0.0747 (12)	0.0677 (11)	0.0003 (8)	0.0114 (8)	0.0080 (9)
O1	0.0483 (6)	0.0960 (10)	0.0732 (8)	−0.0269 (6)	0.0139 (5)	0.0079 (7)
O2	0.0730 (7)	0.0453 (6)	0.0755 (7)	0.0027 (5)	0.0415 (6)	0.0069 (5)

Geometric parameters (Å, º) top

C1—C2	1.374 (2)	C12—H12	0.9300
C1—C6	1.379 (2)	C13—H13	0.9300
C1—H1	0.9300	C14—O2	1.2110 (17)
C2—C3	1.375 (2)	C14—C15	1.5001 (18)
C2—H2	0.9300	C15—C24	1.366 (2)
C3—C4	1.377 (2)	C15—C16	1.410 (2)
C3—H3	0.9300	C16—C17	1.414 (2)
C4—C5	1.385 (2)	C16—C21	1.420 (2)
C4—H4	0.9300	C17—C18	1.362 (2)
C5—C6	1.4039 (18)	C17—H17	0.9300
C5—C14	1.479 (2)	C18—C19	1.410 (3)
C6—C7	1.499 (2)	C18—H18	0.9300
C7—O1	1.2101 (17)	C19—C20	1.347 (3)
C7—C8	1.486 (2)	C19—H19	0.9300
C8—C9	1.382 (2)	C20—C21	1.395 (3)
C8—C13	1.387 (2)	C20—H20	0.9300
C9—C10	1.378 (2)	C21—C22	1.422 (3)
C9—H9	0.9300	C22—C23	1.338 (3)
C10—C11	1.370 (3)	C22—H22	0.9300
C10—H10	0.9300	C23—C24	1.390 (2)
C11—C12	1.371 (3)	C23—H23	0.9300
C11—H11	0.9300	C24—H24	0.9300
C12—C13	1.372 (2)

C2—C1—C6	120.92 (14)	C12—C13—C8	120.36 (15)
C2—C1—H1	119.5	C12—C13—H13	119.8
C6—C1—H1	119.5	C8—C13—H13	119.8
C1—C2—C3	120.22 (14)	O2—C14—C5	121.13 (12)
C1—C2—H2	119.9	O2—C14—C15	119.47 (13)
C3—C2—H2	119.9	C5—C14—C15	119.40 (12)
C4—C3—C2	119.82 (15)	C24—C15—C16	120.76 (14)
C4—C3—H3	120.1	C24—C15—C14	118.79 (14)
C2—C3—H3	120.1	C16—C15—C14	120.31 (13)
C3—C4—C5	120.67 (14)	C15—C16—C17	122.72 (13)
C3—C4—H4	119.7	C15—C16—C21	118.30 (14)
C5—C4—H4	119.7	C17—C16—C21	118.98 (14)
C4—C5—C6	119.25 (13)	C18—C17—C16	120.26 (16)
C4—C5—C14	120.77 (12)	C18—C17—H17	119.9
C6—C5—C14	119.89 (12)	C16—C17—H17	119.9
C1—C6—C5	119.07 (14)	C17—C18—C19	119.9 (2)
C1—C6—C7	117.76 (12)	C17—C18—H18	120.1
C5—C6—C7	123.08 (12)	C19—C18—H18	120.1
O1—C7—C8	121.65 (14)	C20—C19—C18	120.89 (18)
O1—C7—C6	120.12 (13)	C20—C19—H19	119.6
C8—C7—C6	117.94 (11)	C18—C19—H19	119.6
C9—C8—C13	119.01 (14)	C19—C20—C21	120.97 (18)
C9—C8—C7	121.67 (13)	C19—C20—H20	119.5
C13—C8—C7	119.28 (13)	C21—C20—H20	119.5
C10—C9—C8	120.02 (15)	C20—C21—C16	119.00 (19)
C10—C9—H9	120.0	C20—C21—C22	122.68 (17)
C8—C9—H9	120.0	C16—C21—C22	118.31 (16)
C11—C10—C9	120.49 (16)	C23—C22—C21	121.63 (15)
C11—C10—H10	119.8	C23—C22—H22	119.2
C9—C10—H10	119.8	C21—C22—H22	119.2
C10—C11—C12	119.83 (16)	C22—C23—C24	120.17 (18)
C10—C11—H11	120.1	C22—C23—H23	119.9
C12—C11—H11	120.1	C24—C23—H23	119.9
C11—C12—C13	120.28 (16)	C15—C24—C23	120.82 (18)
C11—C12—H12	119.9	C15—C24—H24	119.6
C13—C12—H12	119.9	C23—C24—H24	119.6

C6—C1—C2—C3	−1.1 (2)	C6—C5—C14—O2	11.4 (2)
C1—C2—C3—C4	1.3 (3)	C4—C5—C14—C15	14.2 (2)
C2—C3—C4—C5	0.2 (2)	C6—C5—C14—C15	−169.37 (12)
C3—C4—C5—C6	−1.9 (2)	O2—C14—C15—C24	−87.50 (19)
C3—C4—C5—C14	174.57 (14)	C5—C14—C15—C24	93.24 (17)
C2—C1—C6—C5	−0.6 (2)	O2—C14—C15—C16	88.28 (18)
C2—C1—C6—C7	176.10 (14)	C5—C14—C15—C16	−90.98 (17)
C4—C5—C6—C1	2.1 (2)	C24—C15—C16—C17	−179.91 (15)
C14—C5—C6—C1	−174.38 (13)	C14—C15—C16—C17	4.4 (2)
C4—C5—C6—C7	−174.44 (13)	C24—C15—C16—C21	0.9 (2)
C14—C5—C6—C7	9.1 (2)	C14—C15—C16—C21	−174.84 (13)
C1—C6—C7—O1	64.4 (2)	C15—C16—C17—C18	−177.89 (15)
C5—C6—C7—O1	−118.96 (16)	C21—C16—C17—C18	1.3 (2)
C1—C6—C7—C8	−109.45 (15)	C16—C17—C18—C19	−1.0 (3)
C5—C6—C7—C8	67.15 (18)	C17—C18—C19—C20	0.1 (3)
O1—C7—C8—C9	−163.01 (15)	C18—C19—C20—C21	0.5 (3)
C6—C7—C8—C9	10.8 (2)	C19—C20—C21—C16	−0.1 (3)
O1—C7—C8—C13	14.4 (2)	C19—C20—C21—C22	178.40 (18)
C6—C7—C8—C13	−171.76 (13)	C15—C16—C21—C20	178.49 (15)
C13—C8—C9—C10	0.3 (2)	C17—C16—C21—C20	−0.8 (2)
C7—C8—C9—C10	177.73 (14)	C15—C16—C21—C22	−0.1 (2)
C8—C9—C10—C11	0.2 (2)	C17—C16—C21—C22	−179.36 (14)
C9—C10—C11—C12	0.1 (3)	C20—C21—C22—C23	−178.77 (18)
C10—C11—C12—C13	−0.7 (3)	C16—C21—C22—C23	−0.2 (3)
C11—C12—C13—C8	1.2 (3)	C21—C22—C23—C24	−0.2 (3)
C9—C8—C13—C12	−0.9 (2)	C16—C15—C24—C23	−1.3 (3)
C7—C8—C13—C12	−178.45 (14)	C14—C15—C24—C23	174.46 (16)
C4—C5—C14—O2	−165.07 (14)	C22—C23—C24—C15	1.0 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cg1ⁱ	0.93	2.71	3.618 (19)	163
C20—H20···Cg2ⁱⁱ	0.93	2.85	3.67 (3)	141

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

Experimental details

Crystal data
Chemical formula	C₂₄H₁₆O₂
M_r	336.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.4105 (3), 9.6218 (3), 17.8497 (5)
β (°)	106.113 (2)
V (Å³)	1717.73 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.22 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.980, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	18980, 4081, 2906
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.135, 1.01
No. of reflections	4081
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.17

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cg1ⁱ	0.93	2.71	3.618 (19)	162.6
C20—H20···Cg2ⁱⁱ	0.93	2.85	3.673 (30)	140.5

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

Acknowledgements

GG and ASP thank Dr. Babu Varghese, SAIF, IIT, Chennai, India for the data collection.

References

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