2-Eth-oxy-6-[(3-methyl-pyridin-2-yl)-imino-meth-yl]phenol.

The title Schiff base compound, C(15)H(16)N(2)O(2), was prepared by the condensation reaction of equimolar quanti-ties of 3-eth-oxy-salicyl-aldehyde with 2-amino-3-methyl-pyridine in methanol. The dihedral angle between the benzene ring and the pyridine ring is 2.6 (2)° and an intra-molecular 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 = 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) 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[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.200

S = 1.03

2849 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −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.

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

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

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

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

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 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

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
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*

	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)

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

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

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