(E)-2-[(2-Hydroxy-ethyl)iminiometh-yl]-6-methoxy-phenolate.

The title Schiff base compound, C(10)H(13)NO(3), obtained by the reaction of 2-hydr-oxy-3-methoxy-benzaldehyde and 2-amino-ethanol in methanol solution, crystallizes in a zwitterionic form, in which the mol-ecule adopts a trans configuration about the central C=N bond. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal structure, mol-ecules are linked into chains by inter-molecular O-H⋯O hydrogen bonding.

Related literature

For related structures, see: Cui et al. (1999 ▶); Dong et al. (2007 ▶); Li et al. (2005 ▶); Ng (2008 ▶); Oshio et al. (2003 ▶); Sun et al. (2006 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H13NO3

M = 195.21

Orthorhombic,

a = 14.148 (6) Å

b = 6.587 (3) Å

c = 10.760 (4) Å

V = 1002.8 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.30 × 0.30 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.974, T max = 0.991

7345 measured reflections

1041 independent reflections

923 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.084

S = 1.07

1041 reflections

127 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.09 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005297/hb2911sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005297/hb2911Isup2.hkl

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

C10H13NO3	F(000) = 416
Mr = 195.21	Dx = 1.293 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1828 reflections
a = 14.148 (6) Å	θ = 2.9–20.4°
b = 6.587 (3) Å	µ = 0.10 mm−1
c = 10.760 (4) Å	T = 295 K
V = 1002.8 (7) Å3	Block, yellow
Z = 4	0.30 × 0.30 × 0.12 mm

Bruker APEX CCD diffractometer	1041 independent reflections
Radiation source: fine-focus sealed tube	923 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 26.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −17→17
Tmin = 0.974, Tmax = 0.991	k = −8→8
7345 measured reflections	l = −12→13

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0473P)2 + 0.0337P] where P = (Fo2 + 2Fc2)/3
1041 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.09 e Å−3
1 restraint	Δρmin = −0.15 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	0.53278 (16)	0.7444 (3)	0.0860 (2)	0.0408 (5)
C2	0.57651 (16)	0.9338 (3)	0.0535 (2)	0.0451 (6)
C3	0.69788 (18)	1.1717 (4)	0.1022 (3)	0.0718 (9)
H3A	0.6519	1.2763	0.1164	0.108*
H3B	0.7207	1.1807	0.0183	0.108*
H3C	0.7497	1.1885	0.1588	0.108*
C4	0.5396 (2)	1.0535 (4)	−0.0390 (3)	0.0557 (7)
H4	0.5680	1.1776	−0.0566	0.067*
C5	0.4599 (2)	0.9927 (5)	−0.1078 (3)	0.0625 (8)
H5	0.4366	1.0750	−0.1710	0.075*
C6	0.41744 (18)	0.8135 (4)	−0.0814 (3)	0.0570 (7)
H6	0.3655	0.7718	−0.1278	0.068*
C7	0.45145 (15)	0.6891 (4)	0.0160 (2)	0.0436 (5)
C8	0.39971 (16)	0.5130 (4)	0.0485 (2)	0.0460 (6)
H8	0.3479	0.4790	−0.0006	0.055*
C9	0.36073 (17)	0.2262 (4)	0.1804 (3)	0.0535 (6)
H9A	0.4005	0.1091	0.1961	0.064*
H9B	0.3173	0.1915	0.1140	0.064*
C10	0.30532 (16)	0.2758 (4)	0.2962 (3)	0.0529 (6)
H10A	0.2717	0.1553	0.3232	0.064*
H10B	0.3490	0.3137	0.3617	0.064*
N1	0.41934 (14)	0.3958 (3)	0.1415 (2)	0.0478 (5)
H1	0.4701	0.4199	0.1829	0.057*
O1	0.56592 (11)	0.6322 (2)	0.17429 (18)	0.0486 (4)
O2	0.65545 (11)	0.9784 (3)	0.1213 (2)	0.0564 (5)
O3	0.23996 (12)	0.4345 (2)	0.2785 (2)	0.0584 (5)
H3	0.1946	0.3924	0.2387	0.088*

	U11	U22	U33	U12	U13	U23
C1	0.0358 (11)	0.0387 (12)	0.0478 (13)	0.0046 (9)	0.0063 (10)	−0.0074 (11)
C2	0.0393 (12)	0.0407 (13)	0.0553 (16)	0.0030 (10)	0.0127 (11)	−0.0106 (12)
C3	0.0623 (17)	0.0421 (15)	0.111 (3)	−0.0143 (14)	0.0175 (19)	−0.0154 (16)
C4	0.0608 (17)	0.0435 (14)	0.0629 (17)	0.0038 (13)	0.0206 (15)	0.0050 (13)
C5	0.0670 (18)	0.0703 (19)	0.0502 (16)	0.0090 (15)	0.0064 (14)	0.0132 (15)
C6	0.0507 (14)	0.0726 (18)	0.0477 (15)	0.0022 (13)	−0.0017 (12)	0.0014 (14)
C7	0.0378 (12)	0.0484 (13)	0.0445 (13)	0.0014 (11)	0.0028 (10)	−0.0071 (12)
C8	0.0341 (12)	0.0521 (14)	0.0520 (14)	0.0004 (10)	−0.0026 (11)	−0.0117 (12)
C9	0.0420 (13)	0.0424 (13)	0.0760 (18)	−0.0020 (10)	−0.0002 (14)	0.0002 (13)
C10	0.0422 (12)	0.0533 (15)	0.0633 (16)	0.0033 (11)	−0.0071 (12)	0.0138 (13)
N1	0.0354 (10)	0.0481 (12)	0.0600 (14)	−0.0036 (9)	−0.0025 (9)	−0.0050 (11)
O1	0.0400 (8)	0.0440 (9)	0.0619 (11)	−0.0040 (7)	−0.0082 (8)	0.0003 (9)
O2	0.0436 (9)	0.0433 (9)	0.0822 (14)	−0.0083 (8)	0.0020 (9)	−0.0062 (9)
O3	0.0410 (9)	0.0591 (10)	0.0750 (13)	0.0088 (9)	−0.0069 (9)	−0.0038 (10)

C1—O1	1.291 (3)	C6—H6	0.9300
C1—C7	1.423 (3)	C7—C8	1.416 (3)
C1—C2	1.436 (3)	C8—N1	1.294 (3)
C2—O2	1.366 (3)	C8—H8	0.9300
C2—C4	1.373 (4)	C9—N1	1.453 (3)
C3—O2	1.422 (3)	C9—C10	1.508 (4)
C3—H3A	0.9600	C9—H9A	0.9700
C3—H3B	0.9600	C9—H9B	0.9700
C3—H3C	0.9600	C10—O3	1.409 (3)
C4—C5	1.407 (4)	C10—H10A	0.9700
C4—H4	0.9300	C10—H10B	0.9700
C5—C6	1.355 (4)	N1—H1	0.8600
C5—H5	0.9300	O3—H3	0.8200
C6—C7	1.415 (4)
O1—C1—C7	122.5 (2)	C6—C7—C1	121.3 (2)
O1—C1—C2	121.3 (2)	C8—C7—C1	119.8 (2)
C7—C1—C2	116.2 (2)	N1—C8—C7	124.6 (2)
O2—C2—C4	125.1 (2)	N1—C8—H8	117.7
O2—C2—C1	114.1 (2)	C7—C8—H8	117.7
C4—C2—C1	120.8 (2)	N1—C9—C10	111.6 (2)
O2—C3—H3A	109.5	N1—C9—H9A	109.3
O2—C3—H3B	109.5	C10—C9—H9A	109.3
H3A—C3—H3B	109.5	N1—C9—H9B	109.3
O2—C3—H3C	109.5	C10—C9—H9B	109.3
H3A—C3—H3C	109.5	H9A—C9—H9B	108.0
H3B—C3—H3C	109.5	O3—C10—C9	113.0 (2)
C2—C4—C5	121.5 (2)	O3—C10—H10A	109.0
C2—C4—H4	119.2	C9—C10—H10A	109.0
C5—C4—H4	119.2	O3—C10—H10B	109.0
C6—C5—C4	119.5 (3)	C9—C10—H10B	109.0
C6—C5—H5	120.2	H10A—C10—H10B	107.8
C4—C5—H5	120.2	C8—N1—C9	124.0 (2)
C5—C6—C7	120.6 (3)	C8—N1—H1	118.0
C5—C6—H6	119.7	C9—N1—H1	118.0
C7—C6—H6	119.7	C2—O2—C3	117.4 (2)
C6—C7—C8	118.8 (2)	C10—O3—H3	109.5
O1—C1—C2—O2	1.6 (3)	C2—C1—C7—C6	1.1 (3)
C7—C1—C2—O2	−178.65 (19)	O1—C1—C7—C8	4.8 (3)
O1—C1—C2—C4	−178.8 (2)	C2—C1—C7—C8	−175.0 (2)
C7—C1—C2—C4	1.0 (3)	C6—C7—C8—N1	−174.5 (2)
O2—C2—C4—C5	177.5 (2)	C1—C7—C8—N1	1.8 (3)
C1—C2—C4—C5	−2.1 (3)	N1—C9—C10—O3	63.7 (3)
C2—C4—C5—C6	1.0 (4)	C7—C8—N1—C9	174.2 (2)
C4—C5—C6—C7	1.2 (4)	C10—C9—N1—C8	−104.5 (3)
C5—C6—C7—C8	174.0 (2)	C4—C2—O2—C3	5.8 (3)
C5—C6—C7—C1	−2.2 (4)	C1—C2—O2—C3	−174.6 (2)
O1—C1—C7—C6	−179.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.95	2.617 (2)	134
O3—H3···O1i	0.82	1.95	2.741 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.95	2.617 (2)	134
O3—H3⋯O1i	0.82	1.95	2.741 (3)	161

Symmetry code: (i) .