2'-acetonaphthone.

IN THE STRUCTURE OF THE TITLE COMPOUND [SYSTEMATIC NAME: 1-(naphthalen-2-yl)ethanone], C(12)H(10)O, the acetyl group is approximately coplanar with the naphthalene ring with a C(ar)-C(ar)-C=O torsion angle of 5.8 (2)°. In the crystal, the mol-ecules are packed in a classic herringbone arrangement typical for aromatic polycycles such as penta-cene. They are also linked by weak end-to-end C-H⋯O interactions along the ac diagonal.

Related literature

For synthesis details, see: Bassilios & Salem (1952 ▶). For related structures, see: Kemperman et al. (2000 ▶); Mattheus et al. (2001 ▶); Miyake et al. (1998 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C12H10O

M = 170.20

Monoclinic,

a = 5.9875 (5) Å

b = 7.4025 (7) Å

c = 20.2778 (18) Å

β = 93.747 (1)°

V = 896.84 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.3 × 0.25 × 0.2 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.701, T max = 0.746

12546 measured reflections

2089 independent reflections

1840 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.118

S = 1.08

2089 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812039554/hg5250sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039554/hg5250Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812039554/hg5250Isup3.cml

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

C12H10O	F(000) = 360
Mr = 170.20	Dx = 1.261 Mg m−3
Monoclinic, P21/n	Melting point: 326.7 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 5.9875 (5) Å	Cell parameters from 7818 reflections
b = 7.4025 (7) Å	θ = 2.8–27.6°
c = 20.2778 (18) Å	µ = 0.08 mm−1
β = 93.747 (1)°	T = 173 K
V = 896.84 (14) Å3	Block, colourless
Z = 4	0.3 × 0.25 × 0.2 mm

Bruker APEXII CCD area-detector diffractometer	2089 independent reflections
Radiation source: fine-focus sealed tube, Bruker D8	1840 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 66.06 pixels mm-1	θmax = 27.6°, θmin = 2.0°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −9→9
Tmin = 0.701, Tmax = 0.746	l = −26→26
12546 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0634P)2 + 0.1624P] where P = (Fo2 + 2Fc2)/3
2089 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. A crystal coated in Paratone (TM) oil was mounted on the end of a thin glass capillary and cooled in the gas stream of the diffractometer Kryoflex device.

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
O1	0.29572 (15)	0.31555 (14)	−0.00905 (4)	0.0539 (3)
C1	0.60105 (15)	0.27553 (12)	0.14913 (4)	0.0256 (2)
H1	0.7348	0.2220	0.1356	0.031*
C2	0.43438 (16)	0.32203 (13)	0.10228 (4)	0.0274 (2)
C3	0.23586 (16)	0.40517 (13)	0.12238 (5)	0.0301 (2)
H3	0.1214	0.4389	0.0901	0.036*
C4	0.20800 (15)	0.43702 (13)	0.18753 (5)	0.0284 (2)
H4	0.0745	0.4931	0.2001	0.034*
C5	0.37603 (15)	0.38738 (12)	0.23698 (4)	0.0246 (2)
C6	0.35241 (17)	0.41832 (13)	0.30521 (5)	0.0298 (2)
H6	0.2199	0.4731	0.3191	0.036*
C7	0.51965 (17)	0.36962 (14)	0.35120 (5)	0.0330 (2)
H7	0.5016	0.3906	0.3968	0.040*
C8	0.71788 (17)	0.28884 (14)	0.33168 (5)	0.0325 (2)
H8	0.8322	0.2554	0.3641	0.039*
C9	0.74625 (15)	0.25840 (13)	0.26613 (5)	0.0280 (2)
H9	0.8809	0.2048	0.2533	0.034*
C10	0.57636 (15)	0.30626 (12)	0.21724 (4)	0.0237 (2)
C11	0.45374 (18)	0.28604 (15)	0.03043 (5)	0.0351 (3)
C12	0.6697 (2)	0.21278 (19)	0.00735 (5)	0.0450 (3)
H12A	0.6551	0.1955	−0.0407	0.067*
H12B	0.7035	0.0967	0.0290	0.067*
H12C	0.7910	0.2984	0.0187	0.067*

	U11	U22	U33	U12	U13	U23
O1	0.0509 (5)	0.0794 (7)	0.0299 (4)	0.0071 (5)	−0.0076 (4)	−0.0073 (4)
C1	0.0253 (4)	0.0241 (4)	0.0279 (5)	0.0005 (3)	0.0048 (3)	−0.0005 (3)
C2	0.0296 (5)	0.0268 (5)	0.0257 (5)	−0.0027 (4)	0.0024 (4)	0.0000 (3)
C3	0.0264 (5)	0.0310 (5)	0.0323 (5)	0.0004 (4)	−0.0022 (4)	0.0037 (4)
C4	0.0238 (4)	0.0264 (5)	0.0355 (5)	0.0024 (3)	0.0041 (4)	0.0015 (4)
C5	0.0246 (4)	0.0206 (4)	0.0291 (5)	−0.0024 (3)	0.0050 (3)	−0.0001 (3)
C6	0.0311 (5)	0.0280 (5)	0.0313 (5)	−0.0035 (4)	0.0090 (4)	−0.0030 (4)
C7	0.0386 (5)	0.0357 (5)	0.0254 (4)	−0.0101 (4)	0.0062 (4)	−0.0031 (4)
C8	0.0319 (5)	0.0355 (5)	0.0293 (5)	−0.0068 (4)	−0.0035 (4)	0.0047 (4)
C9	0.0250 (4)	0.0277 (5)	0.0312 (5)	−0.0004 (3)	0.0013 (4)	0.0032 (4)
C10	0.0237 (4)	0.0207 (4)	0.0268 (4)	−0.0017 (3)	0.0027 (3)	0.0014 (3)
C11	0.0404 (6)	0.0376 (6)	0.0270 (5)	−0.0032 (4)	0.0007 (4)	−0.0017 (4)
C12	0.0473 (6)	0.0594 (8)	0.0290 (5)	0.0020 (5)	0.0086 (4)	−0.0075 (5)

O1—C11	1.2185 (13)	C6—C7	1.3712 (14)
C1—C2	1.3759 (13)	C6—H6	0.9500
C1—C10	1.4169 (12)	C7—C8	1.4086 (15)
C1—H1	0.9500	C7—H7	0.9500
C2—C3	1.4216 (13)	C8—C9	1.3697 (14)
C2—C11	1.4931 (13)	C8—H8	0.9500
C3—C4	1.3629 (14)	C9—C10	1.4181 (12)
C3—H3	0.9500	C9—H9	0.9500
C4—C5	1.4215 (13)	C11—C12	1.5046 (16)
C4—H4	0.9500	C12—H12A	0.9800
C5—C6	1.4186 (13)	C12—H12B	0.9800
C5—C10	1.4220 (12)	C12—H12C	0.9800
C2—C1—C10	121.04 (8)	C8—C7—H7	119.6
C2—C1—H1	119.5	C9—C8—C7	120.18 (9)
C10—C1—H1	119.5	C9—C8—H8	119.9
C1—C2—C3	119.51 (8)	C7—C8—H8	119.9
C1—C2—C11	122.01 (9)	C8—C9—C10	120.56 (9)
C3—C2—C11	118.47 (9)	C8—C9—H9	119.7
C4—C3—C2	120.69 (8)	C10—C9—H9	119.7
C4—C3—H3	119.7	C1—C10—C9	121.70 (8)
C2—C3—H3	119.7	C1—C10—C5	119.06 (8)
C3—C4—C5	120.88 (8)	C9—C10—C5	119.24 (8)
C3—C4—H4	119.6	O1—C11—C2	120.18 (10)
C5—C4—H4	119.6	O1—C11—C12	120.42 (10)
C6—C5—C4	122.35 (8)	C2—C11—C12	119.40 (9)
C6—C5—C10	118.84 (8)	C11—C12—H12A	109.5
C4—C5—C10	118.80 (8)	C11—C12—H12B	109.5
C7—C6—C5	120.39 (9)	H12A—C12—H12B	109.5
C7—C6—H6	119.8	C11—C12—H12C	109.5
C5—C6—H6	119.8	H12A—C12—H12C	109.5
C6—C7—C8	120.78 (9)	H12B—C12—H12C	109.5
C6—C7—H7	119.6
C10—C1—C2—C3	1.13 (14)	C2—C1—C10—C9	179.74 (8)
C10—C1—C2—C11	−178.17 (8)	C2—C1—C10—C5	−0.33 (14)
C1—C2—C3—C4	−0.85 (14)	C8—C9—C10—C1	−179.72 (8)
C11—C2—C3—C4	178.47 (9)	C8—C9—C10—C5	0.34 (14)
C2—C3—C4—C5	−0.25 (15)	C6—C5—C10—C1	−179.82 (8)
C3—C4—C5—C6	−179.92 (9)	C4—C5—C10—C1	−0.75 (13)
C3—C4—C5—C10	1.04 (14)	C6—C5—C10—C9	0.11 (13)
C4—C5—C6—C7	−179.44 (8)	C4—C5—C10—C9	179.19 (8)
C10—C5—C6—C7	−0.40 (14)	C1—C2—C11—O1	174.03 (10)
C5—C6—C7—C8	0.25 (15)	C3—C2—C11—O1	−5.28 (16)
C6—C7—C8—C9	0.22 (15)	C1—C2—C11—C12	−5.85 (16)
C7—C8—C9—C10	−0.51 (15)	C3—C2—C11—C12	174.85 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1i	0.95	2.65	3.324 (1)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1i	0.95	2.65	3.324 (1)	129

Symmetry code: (i) .