2-Eth-oxy-6-[(methyl-imino)-meth-yl]phenol.

In the title compound, C(10)H(13)NO(2), synthesized by the reaction of 2-hy-droxy-3-eth-oxy-benzaldehyde with methyl-amine, there is an an intra-molecular O-H⋯N hydrogen bond involving the hy-droxy substituent and the amino N atom. In the crystal, mol-ecules form inversion dimers connected by pairs of C-H⋯O hydrogen bonds.

Related literature

For similar Schiff bases, see: Chatziefthimiou et al. (2006 ▶); Zhang et al. (2003 ▶); Kargar et al. (2010 ▶). For related structures, see: Karadayı et al. (2003 ▶); Che et al. (2002 ▶); Jia et al. (2009 ▶); Fun et al. (2009 ▶). For structures with similar hydrogen-bonding to the title compound, see: Wang et al. (2010 ▶); Kargar et al. (2010 ▶).

Experimental

Crystal data

C10H13NO2

M = 179.21

Monoclinic,

a = 9.2986 (19) Å

b = 14.713 (3) Å

c = 7.0551 (15) Å

β = 108.465 (8)°

V = 915.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.23 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

5022 measured reflections

1611 independent reflections

1338 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.085

wR(F 2) = 0.277

S = 1.01

1611 reflections

122 parameters

H-atom parameters constrained

Δρmax = 0.86 e Å−3

Δρmin = −0.58 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810019951/su2178sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019951/su2178Isup2.hkl

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

C10H13NO2	F(000) = 384
Mr = 179.21	Dx = 1.300 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1611 reflections
a = 9.2986 (19) Å	θ = 2.3–25.0°
b = 14.713 (3) Å	µ = 0.09 mm−1
c = 7.0551 (15) Å	T = 296 K
β = 108.465 (8)°	Block, yellow
V = 915.5 (3) Å3	0.23 × 0.18 × 0.15 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1338 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
graphite	θmax = 25.0°, θmin = 2.3°
phi and ω scans	h = −10→11
5022 measured reflections	k = −17→17
1611 independent reflections	l = −8→6

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.085	H-atom parameters constrained
wR(F2) = 0.277	w = 1/[σ2(Fo2) + (0.1633P)2 + 1.1252P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.002
1611 reflections	Δρmax = 0.86 e Å−3
122 parameters	Δρmin = −0.58 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (11)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	−0.0203 (4)	0.1015 (2)	0.8638 (5)	0.0465 (9)
C2	−0.1745 (4)	0.0879 (2)	0.8267 (5)	0.0477 (9)
C3	−0.2406 (4)	0.1178 (3)	0.9696 (6)	0.0592 (10)
H3	−0.3434	0.1084	0.9482	0.071*
C4	−0.1544 (5)	0.1603 (3)	1.1393 (6)	0.0654 (11)
H4	−0.2000	0.1813	1.2308	0.078*
C5	0.0000 (5)	0.1728 (3)	1.1776 (6)	0.0578 (10)
H5	0.0577	0.2010	1.2952	0.069*
C6	0.0682 (4)	0.1432 (2)	1.0401 (5)	0.0481 (9)
C7	0.3157 (4)	0.1927 (3)	1.2361 (6)	0.0579 (10)
H7A	0.3057	0.1632	1.3542	0.069*
H7B	0.2889	0.2563	1.2391	0.069*
C8	0.4756 (5)	0.1841 (4)	1.2314 (7)	0.0727 (12)
H8A	0.4942	0.1223	1.2015	0.109*
H8B	0.5451	0.2007	1.3592	0.109*
H8C	0.4897	0.2236	1.1304	0.109*
C9	−0.2684 (4)	0.0421 (3)	0.6471 (5)	0.0535 (9)
H9	−0.3714	0.0343	0.6271	0.064*
C10	−0.3148 (3)	−0.0314 (2)	0.3564 (4)	0.0407 (8)
H10A	−0.3663	−0.0781	0.4052	0.061*
H10B	−0.2616	−0.0583	0.2741	0.061*
H10C	−0.3875	0.0116	0.2792	0.061*
N1	−0.2115 (3)	0.0129 (2)	0.5180 (5)	0.0556 (9)
O1	0.0527 (3)	0.0762 (2)	0.7326 (4)	0.0612 (9)
H1	−0.0096	0.0596	0.6275	0.092*
O2	0.2187 (3)	0.15026 (19)	1.0599 (4)	0.0590 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0514 (19)	0.0426 (17)	0.0509 (19)	0.0052 (14)	0.0240 (15)	0.0028 (14)
C2	0.0478 (19)	0.0433 (17)	0.054 (2)	0.0058 (14)	0.0193 (15)	0.0042 (14)
C3	0.052 (2)	0.063 (2)	0.070 (2)	0.0072 (17)	0.0295 (18)	−0.0009 (19)
C4	0.065 (2)	0.075 (3)	0.067 (2)	0.0070 (19)	0.036 (2)	−0.013 (2)
C5	0.063 (2)	0.058 (2)	0.057 (2)	0.0007 (17)	0.0261 (18)	−0.0085 (17)
C6	0.0512 (19)	0.0442 (17)	0.0526 (19)	0.0023 (14)	0.0215 (16)	−0.0013 (14)
C7	0.057 (2)	0.061 (2)	0.056 (2)	−0.0070 (17)	0.0180 (17)	−0.0089 (17)
C8	0.055 (2)	0.091 (3)	0.070 (3)	−0.003 (2)	0.018 (2)	−0.005 (2)
C9	0.0439 (18)	0.059 (2)	0.058 (2)	0.0032 (15)	0.0174 (16)	0.0038 (17)
C10	0.0279 (14)	0.0597 (19)	0.0317 (15)	−0.0057 (12)	0.0057 (11)	−0.0128 (13)
N1	0.0500 (17)	0.0607 (19)	0.0542 (18)	−0.0019 (13)	0.0140 (15)	−0.0045 (14)
O1	0.0486 (15)	0.0812 (19)	0.0581 (16)	−0.0025 (13)	0.0229 (12)	−0.0191 (13)
O2	0.0493 (15)	0.0723 (17)	0.0597 (16)	−0.0071 (12)	0.0233 (12)	−0.0153 (12)

C1—O1	1.362 (4)	C7—C8	1.503 (6)
C1—C2	1.388 (5)	C7—H7A	0.9700
C1—C6	1.398 (5)	C7—H7B	0.9700
C2—C3	1.406 (5)	C8—H8A	0.9600
C2—C9	1.457 (5)	C8—H8B	0.9600
C3—C4	1.364 (6)	C8—H8C	0.9600
C3—H3	0.9300	C9—N1	1.264 (5)
C4—C5	1.387 (6)	C9—H9	0.9300
C4—H4	0.9300	C10—N1	1.398 (4)
C5—C6	1.386 (5)	C10—H10A	0.9600
C5—H5	0.9300	C10—H10B	0.9600
C6—O2	1.366 (4)	C10—H10C	0.9600
C7—O2	1.428 (4)	O1—H1	0.8200
O1—C1—C2	122.7 (3)	O2—C7—H7B	110.2
O1—C1—C6	116.4 (3)	C8—C7—H7B	110.2
C2—C1—C6	120.8 (3)	H7A—C7—H7B	108.5
C1—C2—C3	118.7 (3)	C7—C8—H8A	109.5
C1—C2—C9	121.9 (3)	C7—C8—H8B	109.5
C3—C2—C9	119.4 (3)	H8A—C8—H8B	109.5
C4—C3—C2	120.3 (3)	C7—C8—H8C	109.5
C4—C3—H3	119.9	H8A—C8—H8C	109.5
C2—C3—H3	119.9	H8B—C8—H8C	109.5
C3—C4—C5	121.1 (3)	N1—C9—C2	120.8 (3)
C3—C4—H4	119.5	N1—C9—H9	119.6
C5—C4—H4	119.5	C2—C9—H9	119.6
C6—C5—C4	119.8 (4)	N1—C10—H10A	109.5
C6—C5—H5	120.1	N1—C10—H10B	109.5
C4—C5—H5	120.1	H10A—C10—H10B	109.5
O2—C6—C5	125.8 (3)	N1—C10—H10C	109.5
O2—C6—C1	114.8 (3)	H10A—C10—H10C	109.5
C5—C6—C1	119.3 (3)	H10B—C10—H10C	109.5
O2—C7—C8	107.5 (3)	C9—N1—C10	114.2 (3)
O2—C7—H7A	110.2	C1—O1—H1	109.5
C8—C7—H7A	110.2	C6—O2—C7	117.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.92	2.616 (4)	142
C10—H10B···O1i	0.96	1.98	2.782 (4)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.92	2.616 (4)	142
C10—H10B⋯O1i	0.96	1.98	2.782 (4)	140

Symmetry code: (i) .