Crystal structure of (E)-4-meth-oxy-2-{[(5-methyl-pyridin-2-yl)imino]-meth-yl}phenol.

The mol-ecule of the title Schiff base compound, C14H14N2O2, displays an E conformation with respect the imine C=N double bond. The mol-ecule is approximately planar, with the dihedral angle formed by the planes of the pyridine and benzene rings being 5.72 (6)°. There is an intra-molecular hydrogen bond involving the phenolic H and imine N atoms.

Related literature

For the structure of related N-heterocyclic n class="Chemical">Schiff base compounds, see: Sahebalzamani et al. (2011 ▸); Rawat & Singh (2015 ▸); Thakar et al. (2015 ▸); Salam et al. (2011 ▸).

Experimental

Crystal data

C14H14N2O2

M = 242.27

Monoclinic

a = 12.7082 (12) Å

b = 4.7446 (4) Å

c = 21.124 (2) Å

β = 105.525 (2)°

V = 1227.21 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 294 K

0.41 × 0.35 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SABABS; Bruker, 2014 ▸) T min = 0.030, T max = 0.262

10950 measured reflections

2848 independent reflections

1910 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.151

S = 1.07

2848 reflections

170 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015018113/rz5166sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015018113/rz5166Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015018113/rz5166Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015018113/rz5166fig1.tif

The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. The dashed line indicates an intra­moleculn class="Chemical">ar hydrogen bond.

Click here for additional data file.

b . DOI: 10.1107/S2056989015018113/rz5166fig2.tif

Packing of the title compound compound viewed down the b axis.

Click here for additional data file.

. DOI: 10.1107/S2056989015018113/rz5166fig3.tif

Synthesis of the title compound.

CCDC reference: 1048553

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H14N2O2	F(000) = 512
Mr = 242.27	Dx = 1.311 Mg m−3
Monoclinic, P21/n	Melting point: 380 K
a = 12.7082 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 4.7446 (4) Å	θ = 1.7–27.6°
c = 21.124 (2) Å	µ = 0.09 mm−1
β = 105.525 (2)°	T = 294 K
V = 1227.21 (19) Å3	Block, purple
Z = 4	0.41 × 0.35 × 0.12 mm

Bruker APEXII CCD diffractometer	1910 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.028
Absorption correction: multi-scan (SABABS; Bruker, 2014)	θmax = 27.6°, θmin = 1.7°
Tmin = 0.030, Tmax = 0.262	h = −16→14
10950 measured reflections	k = −6→6
2848 independent reflections	l = −27→27

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.151	w = 1/[σ2(Fo2) + (0.0755P)2 + 0.121P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2848 reflections	Δρmax = 0.17 e Å−3
170 parameters	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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.11027 (10)	0.5504 (3)	0.07471 (7)	0.0866 (5)
O2	0.52254 (10)	0.4026 (3)	0.24106 (6)	0.0762 (4)
N1	0.57565 (9)	−0.2914 (3)	0.07413 (6)	0.0527 (3)
N2	0.55236 (9)	0.0280 (3)	0.15589 (6)	0.0495 (3)
C1	0.63754 (12)	−0.4827 (3)	0.05470 (8)	0.0543 (4)
H1A	0.6101	−0.5632	0.0134	0.065*
C2	0.73934 (11)	−0.5698 (3)	0.09138 (7)	0.0476 (4)
C3	0.77704 (12)	−0.4503 (4)	0.15259 (8)	0.0558 (4)
H3A	0.8446	−0.5033	0.1797	0.067*
C4	0.71504 (12)	−0.2527 (4)	0.17389 (7)	0.0548 (4)
H4A	0.7403	−0.1707	0.2152	0.066*
C5	0.61512 (10)	−0.1780 (3)	0.13323 (7)	0.0445 (3)
C6	0.45685 (12)	0.0882 (3)	0.12034 (8)	0.0521 (4)
H6A	0.4309	−0.0023	0.0801	0.063*
C7	0.38731 (11)	0.2931 (3)	0.14055 (7)	0.0487 (4)
C8	0.42234 (12)	0.4410 (3)	0.19963 (7)	0.0536 (4)
C9	0.35180 (14)	0.6348 (4)	0.21589 (8)	0.0630 (5)
H9A	0.3750	0.7380	0.2545	0.076*
C10	0.24841 (14)	0.6764 (3)	0.17591 (9)	0.0621 (4)
H10A	0.2021	0.8053	0.1880	0.074*
C11	0.21273 (13)	0.5282 (4)	0.11786 (9)	0.0593 (4)
C12	0.28284 (12)	0.3399 (4)	0.10047 (8)	0.0583 (4)
H12A	0.2596	0.2422	0.0610	0.070*
C13	0.80422 (14)	−0.7829 (4)	0.06515 (9)	0.0651 (5)
H13A	0.8653	−0.8443	0.0999	0.098*	0.61 (2)
H13B	0.8302	−0.6989	0.0308	0.098*	0.61 (2)
H13C	0.7587	−0.9416	0.0479	0.098*	0.61 (2)
H13D	0.8763	−0.7110	0.0692	0.098*	0.39 (2)
H13E	0.7689	−0.8191	0.0197	0.098*	0.39 (2)
H13F	0.8090	−0.9547	0.0897	0.098*	0.39 (2)
C14	0.03899 (15)	0.7589 (5)	0.08715 (13)	0.0898 (7)
H14A	−0.0274	0.7588	0.0523	0.135*
H14B	0.0732	0.9404	0.0895	0.135*
H14C	0.0227	0.7192	0.1281	0.135*
H1O2	0.5562 (19)	0.261 (5)	0.2213 (13)	0.120 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0597 (7)	0.0913 (10)	0.1072 (10)	0.0322 (7)	0.0198 (7)	−0.0079 (8)
O2	0.0739 (8)	0.0858 (10)	0.0632 (7)	0.0210 (7)	0.0084 (6)	−0.0106 (7)
N1	0.0450 (6)	0.0544 (7)	0.0554 (7)	0.0084 (6)	0.0076 (5)	−0.0070 (6)
N2	0.0510 (7)	0.0454 (7)	0.0547 (7)	0.0090 (5)	0.0186 (5)	0.0028 (6)
C1	0.0491 (8)	0.0565 (9)	0.0558 (8)	0.0042 (7)	0.0113 (6)	−0.0122 (7)
C2	0.0453 (7)	0.0406 (7)	0.0595 (8)	0.0022 (6)	0.0182 (6)	0.0003 (7)
C3	0.0449 (7)	0.0614 (10)	0.0567 (8)	0.0126 (7)	0.0057 (6)	0.0021 (8)
C4	0.0527 (8)	0.0620 (10)	0.0461 (7)	0.0114 (7)	0.0067 (6)	−0.0049 (7)
C5	0.0448 (7)	0.0409 (7)	0.0494 (7)	0.0047 (6)	0.0151 (6)	0.0012 (6)
C6	0.0520 (8)	0.0489 (8)	0.0578 (8)	0.0094 (7)	0.0187 (7)	0.0000 (7)
C7	0.0524 (8)	0.0419 (7)	0.0576 (8)	0.0073 (6)	0.0247 (7)	0.0058 (7)
C8	0.0619 (9)	0.0489 (8)	0.0553 (8)	0.0079 (7)	0.0248 (7)	0.0076 (7)
C9	0.0803 (11)	0.0557 (9)	0.0618 (9)	0.0118 (9)	0.0342 (9)	−0.0001 (8)
C10	0.0730 (10)	0.0500 (9)	0.0774 (11)	0.0155 (8)	0.0448 (9)	0.0074 (8)
C11	0.0554 (9)	0.0545 (9)	0.0749 (10)	0.0134 (7)	0.0293 (8)	0.0078 (8)
C12	0.0557 (8)	0.0558 (9)	0.0663 (9)	0.0131 (8)	0.0213 (7)	−0.0019 (8)
C13	0.0633 (9)	0.0536 (9)	0.0842 (11)	0.0102 (8)	0.0297 (9)	−0.0057 (9)
C14	0.0614 (10)	0.0771 (13)	0.1362 (19)	0.0267 (10)	0.0357 (11)	0.0035 (13)

O1—C11	1.379 (2)	C7—C12	1.388 (2)
O1—C14	1.413 (2)	C7—C8	1.397 (2)
O2—C8	1.3505 (19)	C8—C9	1.390 (2)
O2—H1O2	0.95 (3)	C9—C10	1.373 (2)
N1—C5	1.3282 (18)	C9—H9A	0.9300
N1—C1	1.3356 (18)	C10—C11	1.381 (2)
N2—C6	1.2771 (18)	C10—H10A	0.9300
N2—C5	1.4231 (17)	C11—C12	1.379 (2)
C1—C2	1.381 (2)	C12—H12A	0.9300
C1—H1A	0.9300	C13—H13A	0.9600
C2—C3	1.375 (2)	C13—H13B	0.9600
C2—C13	1.501 (2)	C13—H13C	0.9600
C3—C4	1.376 (2)	C13—H13D	0.9600
C3—H3A	0.9300	C13—H13E	0.9600
C4—C5	1.3754 (19)	C13—H13F	0.9600
C4—H4A	0.9300	C14—H14A	0.9600
C6—C7	1.4526 (19)	C14—H14B	0.9600
C6—H6A	0.9300	C14—H14C	0.9600
C11—O1—C14	118.00 (16)	C10—C9—H9A	119.4
C8—O2—H1O2	105.5 (15)	C8—C9—H9A	119.4
C5—N1—C1	117.31 (12)	C9—C10—C11	120.38 (14)
C6—N2—C5	119.06 (13)	C9—C10—H10A	119.8
N1—C1—C2	124.82 (14)	C11—C10—H10A	119.8
N1—C1—H1A	117.6	C12—C11—O1	115.88 (16)
C2—C1—H1A	117.6	C12—C11—C10	118.98 (16)
C3—C2—C1	116.25 (13)	O1—C11—C10	125.14 (14)
C3—C2—C13	122.49 (14)	C11—C12—C7	121.46 (16)
C1—C2—C13	121.26 (14)	C11—C12—H12A	119.3
C2—C3—C4	120.18 (13)	C7—C12—H12A	119.3
C2—C3—H3A	119.9	C2—C13—H13A	109.5
C4—C3—H3A	119.9	C2—C13—H13B	109.5
C5—C4—C3	119.02 (14)	H13A—C13—H13B	109.5
C5—C4—H4A	120.5	C2—C13—H13C	109.5
C3—C4—H4A	120.5	H13A—C13—H13C	109.5
N1—C5—C4	122.41 (13)	H13B—C13—H13C	109.5
N1—C5—N2	119.32 (12)	C2—C13—H13D	109.5
C4—C5—N2	118.27 (13)	C2—C13—H13E	109.5
N2—C6—C7	122.28 (14)	H13D—C13—H13E	109.5
N2—C6—H6A	118.9	C2—C13—H13F	109.5
C7—C6—H6A	118.9	H13D—C13—H13F	109.5
C12—C7—C8	119.25 (13)	H13E—C13—H13F	109.5
C12—C7—C6	119.06 (14)	O1—C14—H14A	109.5
C8—C7—C6	121.69 (14)	O1—C14—H14B	109.5
O2—C8—C9	119.18 (15)	H14A—C14—H14B	109.5
O2—C8—C7	122.08 (13)	O1—C14—H14C	109.5
C9—C8—C7	118.74 (15)	H14A—C14—H14C	109.5
C10—C9—C8	121.17 (16)	H14B—C14—H14C	109.5
C5—N1—C1—C2	−0.3 (2)	C12—C7—C8—O2	179.28 (14)
N1—C1—C2—C3	1.0 (2)	C6—C7—C8—O2	0.2 (2)
N1—C1—C2—C13	−178.93 (14)	C12—C7—C8—C9	−1.1 (2)
C1—C2—C3—C4	−0.9 (2)	C6—C7—C8—C9	179.78 (13)
C13—C2—C3—C4	178.97 (14)	O2—C8—C9—C10	−178.66 (14)
C2—C3—C4—C5	0.3 (2)	C7—C8—C9—C10	1.7 (2)
C1—N1—C5—C4	−0.5 (2)	C8—C9—C10—C11	−0.9 (2)
C1—N1—C5—N2	179.64 (12)	C14—O1—C11—C12	−174.24 (16)
C3—C4—C5—N1	0.5 (2)	C14—O1—C11—C10	6.3 (3)
C3—C4—C5—N2	−179.64 (13)	C9—C10—C11—C12	−0.6 (2)
C6—N2—C5—N1	3.8 (2)	C9—C10—C11—O1	178.92 (15)
C6—N2—C5—C4	−176.11 (13)	O1—C11—C12—C7	−178.37 (14)
C5—N2—C6—C7	179.11 (12)	C10—C11—C12—C7	1.2 (3)
N2—C6—C7—C12	−177.58 (14)	C8—C7—C12—C11	−0.3 (2)
N2—C6—C7—C8	1.5 (2)	C6—C7—C12—C11	178.81 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N2	0.95 (2)	1.76 (3)	2.6276 (19)	150 (2)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O2H1O2N2	0.95(2)	1.76(3)	2.6276(19)	150(2)