(1E)-6-Meth­oxy-3,4-dihydro­naphthalen-1(2H)-one oxime

Jin, D.-C.; Piao, F.-Y.; Han, R.-B.

doi:10.1107/S1600536810034574

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2504

doi:10.1107/S1600536810034574

Open

access

(1E)-6-Methoxy-3,4-dihydronaphthalen-1(2H)-one oxime

Da-Cheng Jin,^a Feng-Yu Piao ^b and Rong-Bi Han ^c ^*

^aTesting Center, Yanbian University, Yanji 133000, People's Republic of China, ^bAgricultural College of Yanbian University, Longjing 133400, People's Republic of China, and ^cKey Laboratory of Organism Functional Factors of the Changbai Mountain, Yanbian University, Ministry of Education, Yanji 133000, People's Republic of China
^*Correspondence e-mail: rongbihan@ybu.edu.cn

(Received 12 August 2010; accepted 27 August 2010; online 4 September 2010)

In the crystal structure of the title compound, C₁₁H₁₃NO₂, the molecules are paired into centrosymmetric dimers via intermolecular O—H⋯N hydrogen bonds.

Related literature

For the biological activity of benzazepine derivatives, see: Wei et al. (2009 ). For details of the synthesis, see: Hester (1967 ).

Experimental

Crystal data

C₁₁H₁₃NO₂
M_r = 191.22
Monoclinic, P 2₁ /c
a = 8.185 (6) Å
b = 15.878 (10) Å
c = 8.053 (5) Å
β = 109.02 (3)°
V = 989.4 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 290 K
0.12 × 0.11 × 0.09 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.989, T_max = 0.992
9568 measured reflections
2260 independent reflections
1724 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.140
S = 1.10
2260 reflections
129 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.82	2.09	2.805 (2)	146
Symmetry code: (i) -x, -y, -z+2.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034574/cv2749sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810034574/cv2749Isup2.hkl

checkCIF report

Comment top

As a part of our study of 2,3,4,5-tetrahydro-7-methoxy-1H-2-benzazepin-1-one and its isomer, which exhibit anticonvulsant activities (Wei et al., 2009), we report here the crystal structure of the title compound, which was used in our attempts to improve the selectivity of Backmann rearrangement.

In the title compound (Fig. 1) all bond lengths and angles are normal. Intermolecular O—H···N hydrogen bonds (Table 1) link molecules into centrosymmetric dimer. The cystal packing is further stablized by van der Waals forces.

Related literature top

For the biological activity of benzazepine derivatives, see: Wei et al. (2009). For details of the synthesis, see: Hester (1967).

Experimental top

The title compound was prepared according to the literature (Hester et al., 1967). Colourless single crystals suitable for X-ray diffraction were cultured from a solution of 95% alcohol by slow evaporation at room temperature.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing the atomic numbering. Displacement ellipsoids of non-H atoms are drawn at the 30% probalility level.

(1E)-6-Methoxy-3,4-dihydronaphthalen-1(2H)-one oxime top

Crystal data top

C₁₁H₁₃NO₂	F(000) = 408
M_r = 191.22	D_x = 1.284 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6826 reflections
a = 8.185 (6) Å	θ = 3.1–27.5°
b = 15.878 (10) Å	µ = 0.09 mm⁻¹
c = 8.053 (5) Å	T = 290 K
β = 109.02 (3)°	Block, colourless
V = 989.4 (11) Å³	0.12 × 0.11 × 0.09 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	2260 independent reflections
Radiation source: fine-focus sealed tube	1724 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→9
T_min = 0.989, T_max = 0.992	k = −20→20
9568 measured reflections	l = −10→10

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0809P)² + 0.0477P] where P = (F_o² + 2F_c²)/3
2260 reflections	(Δ/σ)_max = 0.022
129 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₁H₁₃NO₂	V = 989.4 (11) Å³
M_r = 191.22	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.185 (6) Å	µ = 0.09 mm⁻¹
b = 15.878 (10) Å	T = 290 K
c = 8.053 (5) Å	0.12 × 0.11 × 0.09 mm
β = 109.02 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2260 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1724 reflections with I > 2σ(I)
T_min = 0.989, T_max = 0.992	R_int = 0.024
9568 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.10	Δρ_max = 0.14 e Å⁻³
2260 reflections	Δρ_min = −0.20 e Å⁻³
129 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	0.22438 (15)	0.07109 (8)	0.84267 (17)	0.0453 (3)
C2	0.19968 (18)	0.05982 (10)	0.65136 (18)	0.0588 (4)
H2A	0.0874	0.0819	0.5831	0.071*
H2B	0.2007	0.0001	0.6260	0.071*
C3	0.33762 (19)	0.10345 (11)	0.59483 (18)	0.0660 (4)
H3A	0.3314	0.0837	0.4790	0.079*
H3B	0.3160	0.1636	0.5874	0.079*
C4	0.51630 (18)	0.08688 (11)	0.72171 (18)	0.0601 (4)
H4A	0.5418	0.0272	0.7225	0.072*
H4B	0.6009	0.1170	0.6836	0.072*
C5	0.52944 (15)	0.11461 (7)	0.90409 (15)	0.0421 (3)
C6	0.38514 (15)	0.10886 (7)	0.95932 (15)	0.0408 (3)
C7	0.39938 (17)	0.13786 (8)	1.12760 (17)	0.0518 (3)
H7	0.3033	0.1355	1.1650	0.062*
C8	0.55144 (17)	0.16968 (9)	1.23853 (18)	0.0545 (4)
H8	0.5583	0.1883	1.3501	0.065*
C9	0.69544 (15)	0.17400 (8)	1.18325 (16)	0.0466 (3)
C10	0.68406 (15)	0.14690 (8)	1.01691 (16)	0.0454 (3)
H10	0.7803	0.1502	0.9799	0.055*
C11	0.98486 (18)	0.22289 (12)	1.2455 (2)	0.0728 (5)
H11A	1.0245	0.1709	1.2110	0.109*
H11B	1.0762	0.2478	1.3397	0.109*
H11C	0.9512	0.2608	1.1472	0.109*
N1	0.11395 (13)	0.04621 (7)	0.91439 (15)	0.0541 (3)
O1	−0.03579 (13)	0.01124 (8)	0.79076 (14)	0.0707 (4)
H1	−0.0958	−0.0108	0.8427	0.106*
O2	0.84142 (12)	0.20688 (7)	1.30220 (13)	0.0634 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0398 (6)	0.0452 (6)	0.0489 (7)	−0.0035 (5)	0.0115 (5)	−0.0013 (5)
C2	0.0542 (8)	0.0699 (9)	0.0462 (7)	−0.0122 (7)	0.0077 (6)	−0.0058 (6)
C3	0.0646 (9)	0.0886 (11)	0.0403 (7)	−0.0151 (8)	0.0110 (6)	−0.0007 (7)
C4	0.0559 (8)	0.0813 (10)	0.0469 (8)	−0.0102 (7)	0.0219 (6)	−0.0115 (7)
C5	0.0415 (6)	0.0433 (6)	0.0406 (6)	−0.0005 (5)	0.0122 (5)	0.0015 (5)
C6	0.0397 (6)	0.0397 (6)	0.0420 (6)	−0.0028 (5)	0.0117 (5)	0.0004 (5)
C7	0.0469 (7)	0.0615 (8)	0.0516 (8)	−0.0096 (6)	0.0224 (6)	−0.0074 (6)
C8	0.0546 (7)	0.0654 (9)	0.0454 (7)	−0.0120 (6)	0.0190 (6)	−0.0117 (6)
C9	0.0419 (6)	0.0481 (7)	0.0453 (7)	−0.0054 (5)	0.0081 (5)	0.0001 (5)
C10	0.0374 (6)	0.0529 (7)	0.0460 (7)	−0.0019 (5)	0.0137 (5)	0.0019 (5)
C11	0.0445 (7)	0.0990 (13)	0.0673 (10)	−0.0210 (8)	0.0077 (7)	−0.0048 (9)
N1	0.0399 (6)	0.0618 (7)	0.0579 (7)	−0.0126 (5)	0.0124 (5)	−0.0070 (5)
O1	0.0464 (6)	0.0917 (8)	0.0675 (7)	−0.0275 (5)	0.0098 (5)	−0.0114 (6)
O2	0.0465 (5)	0.0848 (7)	0.0525 (6)	−0.0161 (5)	0.0072 (4)	−0.0123 (5)

Geometric parameters (Å, º) top

C1—N1	1.2833 (17)	C6—C7	1.3997 (19)
C1—C6	1.4724 (18)	C7—C8	1.3703 (19)
C1—C2	1.498 (2)	C7—H7	0.9300
C2—C3	1.516 (2)	C8—C9	1.3907 (19)
C2—H2A	0.9700	C8—H8	0.9300
C2—H2B	0.9700	C9—O2	1.3681 (16)
C3—C4	1.509 (2)	C9—C10	1.3808 (19)
C3—H3A	0.9700	C10—H10	0.9300
C3—H3B	0.9700	C11—O2	1.415 (2)
C4—C5	1.5032 (19)	C11—H11A	0.9600
C4—H4A	0.9700	C11—H11B	0.9600
C4—H4B	0.9700	C11—H11C	0.9600
C5—C10	1.3930 (19)	N1—O1	1.4164 (16)
C5—C6	1.3940 (18)	O1—H1	0.8200

N1—C1—C6	116.90 (12)	C5—C6—C7	118.39 (11)
N1—C1—C2	123.19 (12)	C5—C6—C1	119.81 (12)
C6—C1—C2	119.86 (11)	C7—C6—C1	121.79 (11)
C1—C2—C3	112.97 (11)	C8—C7—C6	121.59 (12)
C1—C2—H2A	109.0	C8—C7—H7	119.2
C3—C2—H2A	109.0	C6—C7—H7	119.2
C1—C2—H2B	109.0	C7—C8—C9	119.60 (13)
C3—C2—H2B	109.0	C7—C8—H8	120.2
H2A—C2—H2B	107.8	C9—C8—H8	120.2
C4—C3—C2	111.67 (13)	O2—C9—C10	124.44 (11)
C4—C3—H3A	109.3	O2—C9—C8	115.63 (12)
C2—C3—H3A	109.3	C10—C9—C8	119.93 (12)
C4—C3—H3B	109.3	C9—C10—C5	120.47 (11)
C2—C3—H3B	109.3	C9—C10—H10	119.8
H3A—C3—H3B	107.9	C5—C10—H10	119.8
C5—C4—C3	110.81 (12)	O2—C11—H11A	109.5
C5—C4—H4A	109.5	O2—C11—H11B	109.5
C3—C4—H4A	109.5	H11A—C11—H11B	109.5
C5—C4—H4B	109.5	O2—C11—H11C	109.5
C3—C4—H4B	109.5	H11A—C11—H11C	109.5
H4A—C4—H4B	108.1	H11B—C11—H11C	109.5
C10—C5—C6	120.00 (12)	C1—N1—O1	112.30 (12)
C10—C5—C4	120.37 (11)	N1—O1—H1	109.5
C6—C5—C4	119.62 (11)	C9—O2—C11	118.02 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.82	2.09	2.805 (2)	146

Symmetry code: (i) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃NO₂
M_r	191.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	290
a, b, c (Å)	8.185 (6), 15.878 (10), 8.053 (5)
β (°)	109.02 (3)
V (Å³)	989.4 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.12 × 0.11 × 0.09

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.989, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	9568, 2260, 1724
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.140, 1.10
No. of reflections	2260
No. of parameters	129
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.20

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.82	2.09	2.805 (2)	146.2

Symmetry code: (i) −x, −y, −z+2.

Acknowledgements

We acknowledge financial support from the National Natural Science Foundation of China (grant No. 20662010) and the Specialized Research Fund for the Doctoral Programme of Higher Education (grant No. 2006184001).

References

Hester, J. B. (1967). J. Org. Chem. 32, 3804–3808. CrossRef CAS Web of Science Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wei, C. X., Zhang, W., Quan, Z. S., Han, R. B., Jiang, R. S. & Piao, F. Y. (2009). Lett. Drug Des. Discov. 6, 548–553. Web of Science CrossRef Google Scholar