(2-Benzoyl-phen-yl)(naphthalen-1-yl)methanone.

In the title compound, C(24)H(16)O(2), 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 = 336.37

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.135

S = 1.01

4081 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.17 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039098/bt6830sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039098/bt6830Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039098/bt6830Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C24H16O2	F(000) = 704
Mr = 336.37	Dx = 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

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

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(Fo2) + (0.0682P)2 + 0.3208P] where P = (Fo2 + 2Fc2)/3
4081 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .