2-Eth­oxy-6-[(3-methyl­pyridin-2-yl)­imino­meth­yl]phenol

Yuan, X.-L.

doi:10.1107/S1600536811012116

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1064

doi:10.1107/S1600536811012116

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2-Ethoxy-6-[(3-methylpyridin-2-yl)iminomethyl]phenol

Xiao-Ling Yuan ^a ^*

^aCollege of Chemistry and Biology Engineering, Yichun University, Yichun 336000, People's Republic of China
^*Correspondence e-mail: yuanxiaoling_ycu@126.com

(Received 31 March 2011; accepted 31 March 2011; online 7 April 2011)

The title Schiff base compound, C₁₅H₁₆N₂O₂, was prepared by the condensation reaction of equimolar quantities of 3-ethoxysalicylaldehyde with 2-amino-3-methylpyridine in methanol. The dihedral angle between the benzene ring and the pyridine ring is 2.6 (2)° and an intramolecular O—H⋯N hydrogen bond generates an S(6) ring.

Related literature

For background to Schiff bases, see: Sinha et al. (2008 ); Sonmez et al. (2010 ); Mohamed et al. (2010 ). For related structures, see: Wang & Shi (2008 ); Zhao et al. (2010 ); Karadağ et al. (2011); Bingöl Alpaslan et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₆N₂O₂
M_r = 256.30
Monoclinic, P 2₁ /n
a = 4.820 (1) Å
b = 38.385 (3) Å
c = 7.207 (2) Å
β = 96.381 (2)°
V = 1325.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.985, T_max = 0.987
7773 measured reflections
2849 independent reflections
1265 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.074
wR(F²) = 0.200
S = 1.03
2849 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.87	2.590 (3)	146

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012116/hb5833sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012116/hb5833Isup2.hkl

checkCIF report

Comment top

Much effort has been paid on the preparation, structures, and applications of Schiff bases (Sinha et al., 2008; Sonmez et al., 2010; Mohamed et al., 2010). As a continuation of the work on the crystal structures of Schiff bases, the title new Schiff base compound, Fig. 1, is reported.

The whole molecule of the compound is approximately planar, with a mean deviation from the least squares plane through all 19 non-hydrogen atoms of 0.036 (2) Å; the dihedral angle between the C1–C6 benzene ring and the C8–C12/N2 pyridine ring is 2.6 (2)°. There is an intramolecular O1—H1···N1 hydrogen bond (Table 1), which helps the formation of the planarity of the molecule. The bond lengths and angles are comparable to those found in the similar Schiff base compounds (Wang & Shi, 2008; Zhao et al., 2010; Karadağ et al., 2011; Bingöl Alpaslan et al., 2010).

Related literature top

For background to Schiff bases, see: Sinha et al. (2008); Sonmez et al. (2010); Mohamed et al. (2010). For related structures, see: Wang & Shi (2008); Zhao et al. (2010); Karadağ et al. (2011); Bingöl Alpaslan et al. (2010).

Experimental top

Reagents and solvents used were of commercially available quality. A methanol solution (10 ml) of 2-amino-3-methylpyridine (0.1 mmol, 10.8 mg) was added to a stirred methanol solution (10 ml) of 3-ethoxysalicylaldehyde (0.1 mmol, 16.6 mg). After stirring for about 30 min at room temperature, the clear yellow solution was left to stand still in air. Yellow block-shaped crystals of the title compound were formed after slow evaporation of the solvent for a few days.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound with 30% probability ellipsoids.

2-Ethoxy-6-[(3-methylpyridin-2-yl)iminomethyl]phenol top

Crystal data top

C₁₅H₁₆N₂O₂	F(000) = 544
M_r = 256.30	D_x = 1.285 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 776 reflections
a = 4.820 (1) Å	θ = 2.5–24.5°
b = 38.385 (3) Å	µ = 0.09 mm⁻¹
c = 7.207 (2) Å	T = 298 K
β = 96.381 (2)°	Block, yellow
V = 1325.1 (5) Å³	0.17 × 0.15 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2849 independent reflections
Radiation source: fine-focus sealed tube	1265 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ω scan	θ_max = 27.0°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
T_min = 0.985, T_max = 0.987	k = −49→49
7773 measured reflections	l = −9→9

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.200	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0714P)² + 0.153P] where P = (F_o² + 2F_c²)/3
2849 reflections	(Δ/σ)_max < 0.001
175 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₅H₁₆N₂O₂	V = 1325.1 (5) Å³
M_r = 256.30	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.820 (1) Å	µ = 0.09 mm⁻¹
b = 38.385 (3) Å	T = 298 K
c = 7.207 (2) Å	0.17 × 0.15 × 0.15 mm
β = 96.381 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2849 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1265 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.987	R_int = 0.061
7773 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	0 restraints
wR(F²) = 0.200	H-atom parameters constrained
S = 1.03	Δρ_max = 0.23 e Å⁻³
2849 reflections	Δρ_min = −0.18 e Å⁻³
175 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
N1	0.6449 (5)	0.84753 (6)	0.0653 (4)	0.0495 (7)
N2	0.9399 (6)	0.80518 (7)	0.2233 (4)	0.0604 (8)
O1	0.3096 (5)	0.89291 (6)	−0.1048 (3)	0.0609 (7)
H1	0.4207	0.8767	−0.0957	0.091*
O2	−0.0665 (5)	0.94125 (6)	−0.0911 (3)	0.0691 (7)
C1	0.3479 (6)	0.88351 (8)	0.2257 (5)	0.0508 (8)
C2	0.2310 (6)	0.90021 (8)	0.0638 (4)	0.0458 (8)
C3	0.0320 (7)	0.92615 (8)	0.0768 (5)	0.0550 (9)
C4	−0.0520 (7)	0.93435 (9)	0.2466 (5)	0.0656 (10)
H4	−0.1876	0.9514	0.2543	0.079*
C5	0.0632 (8)	0.91749 (10)	0.4080 (5)	0.0728 (11)
H5	0.0057	0.9234	0.5229	0.087*
C6	0.2592 (7)	0.89243 (9)	0.3978 (5)	0.0625 (10)
H6	0.3351	0.8811	0.5058	0.075*
C7	0.5550 (7)	0.85676 (8)	0.2183 (5)	0.0530 (9)
H7	0.6260	0.8458	0.3286	0.064*
C8	0.8476 (6)	0.82108 (8)	0.0640 (5)	0.0482 (8)
C9	0.9424 (7)	0.81326 (8)	−0.1071 (5)	0.0504 (8)
C10	1.1400 (7)	0.78743 (9)	−0.1066 (5)	0.0603 (10)
H10	1.2096	0.7813	−0.2174	0.072*
C11	1.2348 (7)	0.77076 (9)	0.0558 (6)	0.0666 (10)
H11	1.3680	0.7532	0.0568	0.080*
C12	1.1299 (7)	0.78039 (9)	0.2162 (5)	0.0653 (10)
H12	1.1950	0.7690	0.3263	0.078*
C13	0.8314 (7)	0.83182 (9)	−0.2831 (4)	0.0679 (10)
H13A	0.9225	0.8231	−0.3855	0.102*
H13B	0.8669	0.8563	−0.2689	0.102*
H13C	0.6340	0.8279	−0.3074	0.102*
C14	−0.2849 (7)	0.96607 (9)	−0.0914 (5)	0.0684 (11)
H14A	−0.2220	0.9861	−0.0165	0.082*
H14B	−0.4439	0.9559	−0.0399	0.082*
C15	−0.3642 (9)	0.97670 (11)	−0.2899 (6)	0.0961 (14)
H15A	−0.2014	0.9847	−0.3428	0.144*
H15B	−0.4995	0.9951	−0.2943	0.144*
H15C	−0.4427	0.9571	−0.3600	0.144*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0489 (16)	0.0531 (16)	0.0459 (17)	0.0050 (13)	0.0022 (13)	0.0040 (13)
N2	0.0553 (18)	0.0665 (19)	0.0593 (19)	0.0105 (15)	0.0065 (15)	0.0123 (15)
O1	0.0654 (17)	0.0663 (16)	0.0507 (14)	0.0180 (12)	0.0054 (12)	0.0023 (12)
O2	0.0625 (15)	0.0719 (16)	0.0740 (17)	0.0234 (13)	0.0129 (13)	0.0121 (13)
C1	0.0462 (19)	0.051 (2)	0.054 (2)	0.0012 (16)	0.0037 (16)	−0.0032 (17)
C2	0.0430 (19)	0.0484 (19)	0.046 (2)	−0.0020 (15)	0.0049 (16)	−0.0013 (15)
C3	0.047 (2)	0.053 (2)	0.065 (2)	0.0026 (16)	0.0078 (18)	0.0068 (18)
C4	0.058 (2)	0.064 (2)	0.077 (3)	0.0098 (18)	0.018 (2)	−0.004 (2)
C5	0.074 (3)	0.084 (3)	0.064 (3)	0.013 (2)	0.022 (2)	−0.006 (2)
C6	0.065 (2)	0.077 (2)	0.045 (2)	0.008 (2)	0.0060 (18)	0.0018 (19)
C7	0.056 (2)	0.058 (2)	0.0441 (19)	0.0016 (17)	−0.0005 (17)	0.0029 (16)
C8	0.0435 (19)	0.0469 (19)	0.053 (2)	0.0002 (15)	0.0015 (16)	0.0034 (16)
C9	0.0461 (19)	0.052 (2)	0.052 (2)	−0.0050 (16)	0.0003 (16)	0.0011 (16)
C10	0.059 (2)	0.061 (2)	0.061 (2)	0.0038 (18)	0.0065 (19)	−0.0075 (18)
C11	0.059 (2)	0.059 (2)	0.082 (3)	0.0140 (18)	0.012 (2)	0.004 (2)
C12	0.065 (2)	0.069 (2)	0.063 (2)	0.016 (2)	0.0108 (19)	0.021 (2)
C13	0.073 (3)	0.081 (3)	0.049 (2)	0.007 (2)	0.0033 (19)	0.0014 (19)
C14	0.051 (2)	0.060 (2)	0.094 (3)	0.0129 (18)	0.007 (2)	0.006 (2)
C15	0.099 (3)	0.091 (3)	0.094 (3)	0.045 (3)	−0.007 (3)	0.008 (3)

Geometric parameters (Å, º) top

N1—C7	1.279 (4)	C7—H7	0.9300
N1—C8	1.410 (4)	C8—C9	1.394 (4)
N2—C12	1.326 (4)	C9—C10	1.375 (4)
N2—C8	1.332 (4)	C9—C13	1.500 (4)
O1—C2	1.342 (3)	C10—C11	1.367 (4)
O1—H1	0.8200	C10—H10	0.9300
O2—C3	1.378 (4)	C11—C12	1.363 (5)
O2—C14	1.420 (4)	C11—H11	0.9300
C1—C2	1.394 (4)	C12—H12	0.9300
C1—C6	1.399 (4)	C13—H13A	0.9600
C1—C7	1.437 (4)	C13—H13B	0.9600
C2—C3	1.393 (4)	C13—H13C	0.9600
C3—C4	1.368 (5)	C14—C15	1.496 (5)
C4—C5	1.392 (5)	C14—H14A	0.9700
C4—H4	0.9300	C14—H14B	0.9700
C5—C6	1.356 (4)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600

C7—N1—C8	120.5 (3)	C10—C9—C13	121.7 (3)
C12—N2—C8	117.5 (3)	C8—C9—C13	121.6 (3)
C2—O1—H1	109.5	C11—C10—C9	120.3 (3)
C3—O2—C14	117.8 (3)	C11—C10—H10	119.8
C2—C1—C6	119.6 (3)	C9—C10—H10	119.8
C2—C1—C7	121.0 (3)	C12—C11—C10	118.6 (3)
C6—C1—C7	119.3 (3)	C12—C11—H11	120.7
O1—C2—C3	118.4 (3)	C10—C11—H11	120.7
O1—C2—C1	122.2 (3)	N2—C12—C11	123.4 (3)
C3—C2—C1	119.3 (3)	N2—C12—H12	118.3
C4—C3—O2	125.6 (3)	C11—C12—H12	118.3
C4—C3—C2	120.0 (3)	C9—C13—H13A	109.5
O2—C3—C2	114.5 (3)	C9—C13—H13B	109.5
C3—C4—C5	120.7 (3)	H13A—C13—H13B	109.5
C3—C4—H4	119.7	C9—C13—H13C	109.5
C5—C4—H4	119.7	H13A—C13—H13C	109.5
C6—C5—C4	120.0 (3)	H13B—C13—H13C	109.5
C6—C5—H5	120.0	O2—C14—C15	107.2 (3)
C4—C5—H5	120.0	O2—C14—H14A	110.3
C5—C6—C1	120.4 (3)	C15—C14—H14A	110.3
C5—C6—H6	119.8	O2—C14—H14B	110.3
C1—C6—H6	119.8	C15—C14—H14B	110.3
N1—C7—C1	122.2 (3)	H14A—C14—H14B	108.5
N1—C7—H7	118.9	C14—C15—H15A	109.5
C1—C7—H7	118.9	C14—C15—H15B	109.5
N2—C8—C9	123.5 (3)	H15A—C15—H15B	109.5
N2—C8—N1	119.3 (3)	C14—C15—H15C	109.5
C9—C8—N1	117.2 (3)	H15A—C15—H15C	109.5
C10—C9—C8	116.6 (3)	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.590 (3)	146

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆N₂O₂
M_r	256.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	4.820 (1), 38.385 (3), 7.207 (2)
β (°)	96.381 (2)
V (Å³)	1325.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.17 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.985, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	7773, 2849, 1265
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.200, 1.03
No. of reflections	2849
No. of parameters	175
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.590 (3)	146

Acknowledgements

This work was supported by Yichun University.

References

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