(E)-2-[(2-Hydroxy­ethyl)iminiometh­yl]-6-methoxy­phenolate

Tan, G.-X.; Liu, X.-C.

doi:10.1107/S1600536809005297

organic compounds

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Volume 65| Part 3| March 2009| Page o559

doi:10.1107/S1600536809005297

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(E)-2-[(2-Hydroxyethyl)iminiomethyl]-6-methoxyphenolate

Guo-Xia Tan ^a ^* and Xi-Cheng Liu ^b

^aExperimental & Educational Technology Center, Linyi Normal University, Linyi 276005, People's Republic of China, and ^bDepartment of Chemistry, Qufu Normal University, Qufu 273165, People's Republic of China
^*Correspondence e-mail: guoxiatan@163.com

(Received 13 February 2009; accepted 13 February 2009; online 21 February 2009)

The title Schiff base compound, C₁₀H₁₃NO₃, obtained by the reaction of 2-hydroxy-3-methoxybenzaldehyde and 2-aminoethanol in methanol solution, crystallizes in a zwitterionic form, in which the molecule adopts a trans configuration about the central C=N bond. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal structure, molecules are linked into chains by intermolecular 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_r = 195.21
Orthorhombic, P c a 2₁
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.084
S = 1.07
1041 reflections
127 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.09 e Å⁻³
Δρ_min = −0.15 e Å⁻³

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) $[x-{\script{1\over 2}}, -y+1, z]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

The title compound, (I), derived from 3-methoxy-2-hydroxybenzaldehyde and 2-aminoethanol, is a potential NO₃ tetradentate Schiff base ligand and its complexes with Cd(II), Cu(II), Zn(II) and Fe(III) have been reported (Cui et al., 1999; Dong et al., 2007; Li et al., 2005; Oshio et al., 2003). Here, the structure of (I) is described.

The title molecule exists in a zwitterionic form with a strong intramolecular N—H···O hydrogen bond (Table 1) between the NH⁺ and the phenolate O^-, as shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al.,1987). The N1=C8 [1.294 (3) Å] and N1—C8 [1.453 (3) Å] bond distances are comparable to these found in similar Schiff base compounds, such as 2,4-Dibromo-6-(2-hydroxyethyliminiomethyl)- phenolate [1.277 (5) and 1.451 (4) Å] (Sun et al., 2006) and 4-chloro-2-[tris(hydroxymethyl)methyliminiomethyl]phenolate [1.288 (2) and 1.467 (2) Å] (Ng, 2008). As expected, the molecule adopts a trans configuration about the central C=N bond. In the crystal structure, O3—H3···O1ⁱ (symmetry code as given in Table 1) intermolecular hydrogen bonds formed between the hydroxy and oxygen of phenolate link the molecules into a one-dimension supramolecular chain.

Related literature top

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 top

3-Methoxy-2-hydroxybenzaldehyde (0.152 g, 1 mmol) and equimolar 2-aminoethanol (0.061 g, 1 mmol) were refluxed for 30 min in methanol solution (15 ml). The reaction mixtures were cooled to room temprature and filtered. After keeping the filtrate in air for 3 d, yellow blocks of (I) (yield 66%; mp 338–339 K) were obtained.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of (I) with displacement ellipsoids drawn at the 50% probability level. The N—H···O hydrogen bond is shown as a dashed line.

(E)-2-[(2-Hydroxyethyl)iminiomethyl]-6-methoxyphenolate top

Crystal data top

C₁₀H₁₃NO₃	F(000) = 416
M_r = 195.21	D_x = 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

Data collection top

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

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0473P)² + 0.0337P] where P = (F_o² + 2F_c²)/3
1041 reflections	(Δ/σ)_max < 0.001
127 parameters	Δρ_max = 0.09 e Å⁻³
1 restraint	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₀H₁₃NO₃	V = 1002.8 (7) Å³
M_r = 195.21	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 14.148 (6) Å	µ = 0.10 mm⁻¹
b = 6.587 (3) Å	T = 295 K
c = 10.760 (4) Å	0.30 × 0.30 × 0.12 mm

Data collection top

Bruker APEX CCD diffractometer	1041 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	923 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.991	R_int = 0.037
7345 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	1 restraint
wR(F²) = 0.084	H-atom parameters constrained
S = 1.07	Δρ_max = 0.09 e Å⁻³
1041 reflections	Δρ_min = −0.15 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₃NO₃
M_r	195.21
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	295
a, b, c (Å)	14.148 (6), 6.587 (3), 10.760 (4)
V (Å³)	1002.8 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.30 × 0.12

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.974, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	7345, 1041, 923
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.084, 1.07
No. of reflections	1041
No. of parameters	127
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.09, −0.15

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+1, z.

Acknowledgements

This work was supported by the Key Laboratory of Colloid Interface Chemistry of the Ministry of Education (200707).

References

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