organic compounds
2′-Acetonaphthone
aDepartment of Chemistry and Biochemistry, University of Lethbridge, Lethbridge, AB, Canada T1K3M4
*Correspondence e-mail: boere@uleth.ca
In the structure of the title compound [systematic name: 1-(naphthalen-2-yl)ethanone], C12H10O, the acetyl group is approximately coplanar with the naphthalene ring with a Car—Car—C=O torsion angle of 5.8 (2)°. In the crystal, the molecules are packed in a classic herringbone arrangement typical for aromatic polycycles such as pentacene. 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
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Refinement
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Data collection: APEX2 (Bruker, 2008); cell 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).
Supporting information
10.1107/S1600536812039554/hg5250sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812039554/hg5250Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812039554/hg5250Isup3.cml
Hydrogen atoms attached to carbon were treated as riding, with C—H = 0.98 Å and Uiso(H) = 1.5Ueq(C) for methyl and C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C) for aromatic H atoms.
Data collection: APEX2 (Bruker, 2008); cell
SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus (Bruker, 2008); 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).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 |
C12H10O | V = 896.84 (14) Å3 |
Mr = 170.20 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 5.9875 (5) Å | µ = 0.08 mm−1 |
b = 7.4025 (7) Å | T = 173 K |
c = 20.2778 (18) Å | 0.3 × 0.25 × 0.2 mm |
β = 93.747 (1)° |
Bruker APEXII CCD area-detector diffractometer | 2089 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 1840 reflections with I > 2σ(I) |
Tmin = 0.701, Tmax = 0.746 | Rint = 0.019 |
12546 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.25 e Å−3 |
2089 reflections | Δρmin = −0.23 e Å−3 |
119 parameters |
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 |
Symmetry code: (i) x+1/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C12H10O |
Mr | 170.20 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 5.9875 (5), 7.4025 (7), 20.2778 (18) |
β (°) | 93.747 (1) |
V (Å3) | 896.84 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.3 × 0.25 × 0.2 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.701, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12546, 2089, 1840 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.653 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.118, 1.08 |
No. of reflections | 2089 |
No. of parameters | 119 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.23 |
Computer programs: APEX2 (Bruker, 2008), SAINT-Plus (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2008), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O1i | 0.95 | 2.648 | 3.324 (1) | 128.5 |
Symmetry code: (i) x+1/2, −y+1/2, z+1/2. |
Acknowledgements
The Natural Sciences and Engineering Research Council of Canada (NSERC) is gratefully acknowledged for a Discovery Grant. The diffractometer was purchased with the help of NSERC and the University of Lethbridge.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
2'-Acetonaphthone, (I), is an important example of an aromatic ketone that can be prepared by a classical Friedel-Crafts acylation reaction (Bassilios & Salem, 1952) and is commercially available from many suppliers. A search of the Cambridge Structural Database (Allen, 2002; WebCSD August 2012) returned only two previous crystal structures for (I), in both of which this molecule functions as a guest within an organic host framework. In the structure reported by Kemperman et al. (2000; refcode MEGXUR), (I) is found as a disordered inclusion compound along with four water molecules in a clathrate formed by two cephradine molecules. The cages formed by this cephalosporin antibiotic were shown to be quite flexible and fit guests of differing size, in part by also incorporating varying numbers of hydrogen-bonded water molecules. This adaptability of the host lattice has been described as permitting "induced fitting" of guest molecule(s). The cephradine host molecules fully surround their guests and keep individual molecules of (I) separated by the b axis distance of 7.1965 (3) Å. In the second example (refcode: NECPUG), (I) forms into π-stacks which fill channels that run along the c axis of a lattice formed from the modified bile acid derivative 3-epiursodeoxycholic acid (Miyake et al., 1998). The average separation of molecules of (I) along these channels is 3.51 Å, just 0.1 Å greater than the sums of the van der Waals radii of two carbon atoms. Both of these structures for (I) have very poor precision in the interatomic distances with mean s.u. of 0.01 Å.
We have therefore determined the crystal structure at 173 K of pure (I). Fig. 1 displays the molecular structure as found in the crystal lattice. The acetyl group is approximately co-planar with the naphthalene ring and the carbonyl oxygen is anti to the ring with the torsion angle C1-C2-C11-O1 174.8 (1)°. By comparison, in NECPUG the oxygen atom is in the syn position. The disorder in MEGXUR precludes a definitive conformational assignment, but the major component appears to have the oxygen anti as in (I). It is instructive to compare the bond distances determined for pure (I) with those determined in the host lattices. The high-accuracy structure reported here may also be used to define rigid templates as an aid in refining future inclusion compounds of (I).
In contrast to the host–guest complexes MEGXUR, which has isolated molecules of (I), and NECPUG with π-stacked (I), the crystal packing of pure (I) is of the herringbone 2-D edge-to-face type (Figure 2). This arrangement of crystal packing is reminiscent to that found in pentacene as determined at 90 K (Mattheus et al., 2001). Unlike pentacene, molecules of (I) are also linked by weak end-to-end by C8-H8···O1 intermolecular interactions (Table 1).