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

Abstract

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,

• a = 4.820 (1) Å

• b = 38.385 (3) Å

• c = 7.207 (2) Å

• β = 96.381 (2)°

• V = 1325.1 (5) ų

• 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[F ² > 2σ(F ²)] = 0.074

• wR(F ²) = 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

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.

Supplementary Material

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

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

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

H atoms were placed in calculated positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, O—H distance of 0.82 Å, and with U_iso(H) set to 1.2U_eq(C) and 1.5U_eq(O1, C13 and C15).

Figures

Fig. 1.

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

Crystal data

C15H16N2O2	F(000) = 544
Mr = 256.30	Dx = 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

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

Refinement

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(Fo2) + (0.0714P)2 + 0.153P] where P = (Fo2 + 2Fc2)/3
2849 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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, °)

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