1-(4-Methyl-1-naphth­yl)ethanone

Hu, Y.-H.; Zhao, X.-L.; Yang, W.-G.; Yao, J.-F.; Lu, X.-T.

doi:10.1107/S1600536808035812

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2307

doi:10.1107/S1600536808035812

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1-(4-Methyl-1-naphthyl)ethanone

Yong-Hong Hu,^a ^* Xiao-Lei Zhao,^a Wen-Ge Yang,^a Jin-Feng Yao ^a and Xiu-Tao Lu ^a

^aCollege of Life Science and Pharmaceutical Engineering, Nanjing University of Technolgy, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: hyh@njut.edu.cn

(Received 28 October 2008; accepted 31 October 2008; online 13 November 2008)

In the molecule of the title compound, C₁₃H₁₂O, the two aromatic rings are oriented at a dihedral angle of 2.90 (3)°. An intramolecular C—H⋯O hydrogen bond results in the formation of a non-planar six-membered ring, which adopts an envelope conformation. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules.

Related literature

For related structures, see: Dixon et al. (1981 ); Grummitt & Buck (1943 ); Merritt & Braun (1950 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₃H₁₂O
M_r = 184.23
Orthorhombic, P b c a
a = 15.449 (3) Å
b = 7.8290 (16) Å
c = 16.755 (3) Å
V = 2026.5 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 294 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.978, T_max = 0.993
1932 measured reflections
1846 independent reflections
905 reflections with I > 2σ(I)
R_int = 0.000
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.155
S = 1.01
1846 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O	0.93	2.30	2.920 (4)	124
C13—H13C⋯Oⁱ	0.96	2.55	3.296 (4)	135
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035812/hk2564sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808035812/hk2564Isup2.hkl

checkCIF report

Comment top

The title compound is a dye and plastic processing aid of intermediate, 1,4-naphthalenedicarboxylic acid. As part of our ongoing studies in this area, we report herein its crystal structure.

In the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C3-C8) and B (C1-C3/C8-C10) are, of course, planar and the dihedral angle between them is A/B = 2.90 (3)°. The intramolecular C-H···O hydrogen bond (Table 1) results in the formation of a nonplanar six-membered ring C (C2-C4/C12/O/H2A) adopting envelope conformation with O atom displaced by -0.533 (3) Å from the plane of the other ring atoms.

In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For related structures, see: Dixon et al. (1981); Grummitt & Buck (1943); Merritt & Braun (1950). For bond-length data, see: Allen et al. (1987).

Experimental top

In a three-necked flask, naphthalene (256.0 g, 2.00 mol), paraformaldehyde (110.0 g, 1.22 mol), glacial acetic acid (260 ml), concentrated hydrochloric acid (362 ml) and phosphoric acid (165 ml, 85%) are heated with efficient stirring in a water bath at 353-358 K for 6 h. The product is washed two times with cold water (1 liter), a solution of potassium carbonate (20.0 g) in cold water (500 ml), and finally with cold water (500 ml). Ether (200 ml) is added to the oil layer and the solution is given a preliminary drying with anhydrous potassium carbonate (10.0 g) for 1 h. The lower aqueous layer is separated and the ether solution again dried with potassium carbonate (20.0 g) for 8-10 h. The ether solution is distilled first at atmospheric pressure to remove the ether, and then followed by distillation under reduced pressure to obtain 1-chloromethylnaphthalene. In a three-necked flask, magnesium (63.2 g), absolute ether (100 ml), a crystal of iodine, a solution of 1-chloromethylnaphthalene (150.0 g, 0.85 mol) in absolute ether (750 ml) and absolute ether (1080 ml) are mixed, and the ether solution of the chloride is added to the mixture in 5 h, and then stirred and heated at reflux for an additional 1 h to obtain 1-methylnaphthalene. The yield was 88-92% (Grummitt & Buck, 1943). Acetyl chloride (39.3 g, 0.48 mol, 38 ml) is added over 45 min to a stirred mixture of 1-methylnaphthalene (Aldrich) (67.0 g, 0.48 mol), dry dichloromethane (340 ml) and finely ground anhydrous aluminium chloride (76.0 g, 0.57 mol) at 273 K. After the addition is completed, the mixture is stirred at ambient temperature for 4 h, and then heated under reflux for 2.5 h (Dixon et al., 1981). The reaction solution is washed with hydrochloric acid many times. The aqueous phase followed by distillation under reduced pressure gave the title compound (yield; 71%) (Merritt & Braun, 1950). Crystals suitable for X-ray analysis are obtained by slow evaporation of an petroleum ether solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom- numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bond is shown as dashed line.
	Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines.

1-(4-Methyl-1-naphthyl)ethanone top

Crystal data top

C₁₃H₁₂O	F(000) = 784
M_r = 184.23	D_x = 1.208 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 15.449 (3) Å	θ = 9–13°
b = 7.8290 (16) Å	µ = 0.08 mm⁻¹
c = 16.755 (3) Å	T = 294 K
V = 2026.5 (7) Å³	Block, colorless
Z = 8	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	905 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.3°, θ_min = 2.4°
ω/2θ scans	h = 0→18
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
T_min = 0.978, T_max = 0.993	l = 0→20
1932 measured reflections	3 standard reflections every 120 min
1846 independent reflections	intensity decay: none

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.05P)² + 0.8P] where P = (F_o² + 2F_c²)/3
1846 reflections	(Δ/σ)_max < 0.001
127 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₃H₁₂O	V = 2026.5 (7) Å³
M_r = 184.23	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 15.449 (3) Å	µ = 0.08 mm⁻¹
b = 7.8290 (16) Å	T = 294 K
c = 16.755 (3) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	905 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.978, T_max = 0.993	3 standard reflections every 120 min
1932 measured reflections	intensity decay: none
1846 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.01	Δρ_max = 0.14 e Å⁻³
1846 reflections	Δρ_min = −0.16 e Å⁻³
127 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
O	0.72633 (18)	−0.0605 (3)	0.52877 (14)	0.1022 (9)
C1	0.4927 (2)	0.1819 (5)	0.5918 (2)	0.0830 (11)
H1A	0.4590	0.1827	0.5457	0.100*
C2	0.5750 (2)	0.1221 (4)	0.58895 (18)	0.0665 (9)
H2A	0.5973	0.0829	0.5407	0.080*
C3	0.62766 (19)	0.1181 (3)	0.65824 (17)	0.0498 (7)
C4	0.7163 (2)	0.0658 (3)	0.65707 (18)	0.0573 (8)
C5	0.7619 (2)	0.0651 (4)	0.7276 (2)	0.0679 (9)
H5A	0.8198	0.0326	0.7272	0.082*
C6	0.7234 (2)	0.1121 (4)	0.79985 (19)	0.0710 (10)
H6A	0.7554	0.1034	0.8467	0.085*
C7	0.6410 (2)	0.1698 (4)	0.80342 (17)	0.0611 (8)
C8	0.59134 (18)	0.1753 (3)	0.73121 (18)	0.0531 (7)
C9	0.5063 (2)	0.2390 (5)	0.7314 (2)	0.0731 (10)
H9A	0.4825	0.2794	0.7787	0.088*
C10	0.4583 (2)	0.2424 (4)	0.6633 (3)	0.0829 (11)
H10A	0.4022	0.2854	0.6645	0.100*
C11	0.6043 (3)	0.2281 (5)	0.88156 (17)	0.0941 (13)
H11A	0.6474	0.2163	0.9225	0.141*
H11B	0.5548	0.1597	0.8948	0.141*
H11C	0.5873	0.3457	0.8775	0.141*
C12	0.7628 (3)	0.0157 (4)	0.5827 (2)	0.0733 (10)
C13	0.8571 (2)	0.0651 (4)	0.5755 (2)	0.0961 (13)
H13A	0.8794	0.0259	0.5253	0.144*
H13B	0.8893	0.0137	0.6183	0.144*
H13C	0.8625	0.1871	0.5786	0.144*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O	0.127 (2)	0.098 (2)	0.0814 (16)	−0.0038 (18)	0.0255 (17)	−0.0239 (15)
C1	0.081 (3)	0.079 (3)	0.090 (3)	−0.011 (2)	−0.028 (2)	0.017 (2)
C2	0.078 (2)	0.061 (2)	0.061 (2)	−0.0079 (19)	−0.0101 (18)	0.0077 (16)
C3	0.0557 (18)	0.0421 (16)	0.0516 (16)	−0.0036 (14)	0.0025 (15)	0.0035 (14)
C4	0.066 (2)	0.0455 (17)	0.0601 (18)	−0.0005 (16)	0.0093 (18)	0.0039 (15)
C5	0.063 (2)	0.060 (2)	0.081 (2)	0.0066 (17)	−0.005 (2)	0.0095 (18)
C6	0.079 (3)	0.074 (2)	0.061 (2)	0.000 (2)	−0.0125 (18)	0.0105 (17)
C7	0.073 (2)	0.0565 (19)	0.0535 (18)	−0.0008 (18)	0.0024 (18)	0.0037 (15)
C8	0.0516 (18)	0.0464 (16)	0.0614 (18)	−0.0009 (15)	0.0018 (16)	0.0054 (14)
C9	0.066 (2)	0.074 (2)	0.079 (2)	0.005 (2)	0.010 (2)	0.0109 (19)
C10	0.053 (2)	0.072 (2)	0.124 (3)	−0.0011 (19)	0.000 (2)	0.021 (2)
C11	0.122 (3)	0.101 (3)	0.059 (2)	0.013 (3)	0.011 (2)	−0.004 (2)
C12	0.095 (3)	0.0495 (19)	0.076 (2)	0.0060 (19)	0.021 (2)	0.0012 (18)
C13	0.079 (3)	0.081 (3)	0.128 (3)	0.007 (2)	0.046 (2)	0.004 (2)

Geometric parameters (Å, º) top

O—C12	1.220 (4)	C7—C8	1.434 (4)
C1—C2	1.357 (4)	C7—C11	1.498 (4)
C1—C10	1.394 (5)	C8—C9	1.405 (4)
C1—H1A	0.9300	C9—C10	1.360 (4)
C2—C3	1.418 (4)	C9—H9A	0.9300
C2—H2A	0.9300	C10—H10A	0.9300
C3—C8	1.418 (4)	C11—H11A	0.9600
C3—C4	1.430 (4)	C11—H11B	0.9600
C4—C5	1.376 (4)	C11—H11C	0.9600
C4—C12	1.491 (4)	C12—C13	1.513 (5)
C5—C6	1.398 (4)	C13—H13A	0.9600
C5—H5A	0.9300	C13—H13B	0.9600
C6—C7	1.352 (4)	C13—H13C	0.9600
C6—H6A	0.9300

C2—C1—C10	120.3 (3)	C3—C8—C7	120.4 (3)
C2—C1—H1A	119.9	C10—C9—C8	121.0 (3)
C10—C1—H1A	119.9	C10—C9—H9A	119.5
C1—C2—C3	121.1 (3)	C8—C9—H9A	119.5
C1—C2—H2A	119.4	C9—C10—C1	120.5 (3)
C3—C2—H2A	119.4	C9—C10—H10A	119.8
C8—C3—C2	118.2 (3)	C1—C10—H10A	119.8
C8—C3—C4	118.8 (3)	C7—C11—H11A	109.5
C2—C3—C4	123.0 (3)	C7—C11—H11B	109.5
C5—C4—C3	118.7 (3)	H11A—C11—H11B	109.5
C5—C4—C12	118.1 (3)	C7—C11—H11C	109.5
C3—C4—C12	123.2 (3)	H11A—C11—H11C	109.5
C4—C5—C6	121.7 (3)	H11B—C11—H11C	109.5
C4—C5—H5A	119.2	O—C12—C4	121.7 (3)
C6—C5—H5A	119.2	O—C12—C13	120.8 (3)
C7—C6—C5	121.8 (3)	C4—C12—C13	117.5 (3)
C7—C6—H6A	119.1	C12—C13—H13A	109.5
C5—C6—H6A	119.1	C12—C13—H13B	109.5
C6—C7—C8	118.5 (3)	H13A—C13—H13B	109.5
C6—C7—C11	119.8 (3)	C12—C13—H13C	109.5
C8—C7—C11	121.7 (3)	H13A—C13—H13C	109.5
C9—C8—C3	118.9 (3)	H13B—C13—H13C	109.5
C9—C8—C7	120.6 (3)

C10—C1—C2—C3	0.5 (5)	C2—C3—C8—C7	178.4 (3)
C1—C2—C3—C8	1.3 (4)	C4—C3—C8—C7	−4.1 (4)
C1—C2—C3—C4	−176.1 (3)	C6—C7—C8—C9	−178.1 (3)
C8—C3—C4—C5	3.1 (4)	C11—C7—C8—C9	1.1 (5)
C2—C3—C4—C5	−179.6 (3)	C6—C7—C8—C3	1.2 (4)
C8—C3—C4—C12	−175.4 (3)	C11—C7—C8—C3	−179.5 (3)
C2—C3—C4—C12	2.0 (4)	C3—C8—C9—C10	1.6 (5)
C3—C4—C5—C6	0.8 (5)	C7—C8—C9—C10	−179.1 (3)
C12—C4—C5—C6	179.3 (3)	C8—C9—C10—C1	0.2 (5)
C4—C5—C6—C7	−3.9 (5)	C2—C1—C10—C9	−1.3 (5)
C5—C6—C7—C8	2.7 (5)	C5—C4—C12—O	146.1 (3)
C5—C6—C7—C11	−176.5 (3)	C3—C4—C12—O	−35.4 (5)
C2—C3—C8—C9	−2.3 (4)	C5—C4—C12—C13	−34.8 (4)
C4—C3—C8—C9	175.2 (3)	C3—C4—C12—C13	143.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O	0.93	2.30	2.920 (4)	124
C13—H13C···Oⁱ	0.96	2.55	3.296 (4)	135

Symmetry code: (i) −x+3/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂O
M_r	184.23
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	294
a, b, c (Å)	15.449 (3), 7.8290 (16), 16.755 (3)
V (Å³)	2026.5 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.978, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	1932, 1846, 905
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.155, 1.01
No. of reflections	1846
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.16

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O	0.93	2.30	2.920 (4)	124.00
C13—H13C···Oⁱ	0.96	2.55	3.296 (4)	135.00

Symmetry code: (i) −x+3/2, y+1/2, z.

Acknowledgements

This research work was supported financially by the Department of Science and Technology of Jiangsu Province (BE200830457) and the `863' project (2007AA02Z211) of the Ministry of Science and Technology of P. R. China.

References

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