(1E)-6-Meth-oxy-3,4-dihydro-naphthalen-1(2H)-one oxime.

In the crystal structure of the title compound, C(11)H(13)NO(2), the mol-ecules are paired into centrosymmetric dimers via inter-molecular 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 = 191.22

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.140

S = 1.10

2260 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.20 e Å−3

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.

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

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

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

C11H13NO2	F(000) = 408
Mr = 191.22	Dx = 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

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

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(Fo2) + (0.0809P)2 + 0.0477P] where P = (Fo2 + 2Fc2)/3
2260 reflections	(Δ/σ)max = 0.022
129 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.20 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	0.22438 (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)

	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)

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)

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

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) .