(E)-2-Methyl-6-{[(5-methyl­pyridin-2-yl)imino]­methyl}phenol

In the title compound, C₁₄H₁₄N₂O, the dihedral angle between the aromatic rings is 5.54 (9)°. The conformation is reinforced by an intra­molecular O—H...N hydrogen bond, which closes an S(6) ring. The pyridine N atom and methyl group lie to opposite sides of the mol­ecule. In the crystal, the mol­ecules are linked into a zigzag chain propagating in [0-11] by weak C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.112
• Data-to-parameter ratio = 19.4

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015).

(E)-2-Methyl-6-{[(5-methylpyridin-2-yl)imino]methyl}phenol

Crystal data

C14H14N2O	Dx = 1.301 Mg m^−3
Mr = 226.27	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 2856 reflections
a = 23.440 (3) Å	θ = 2.6–29.1°
b = 4.6307 (6) Å	µ = 0.08 mm^−1
c = 10.6408 (13) Å	T = 100 K
V = 1155.0 (3) Å^3	Block, orange
Z = 4	0.59 × 0.18 × 0.14 mm
F(000) = 480

Data collection

Bruker APEXII CCD diffractometer	Rint = 0.031
φ and ω scans	θmax = 29.1°, θmin = 1.7°
9247 measured reflections	h = −31→31
3106 independent reflections	k = −6→6
2792 reflections with I > 2σ(I)	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0653P)^2 + 0.0393P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
3106 reflections	Δρmax = 0.25 e Å^−3
160 parameters	Δρmin = −0.18 e Å^−3
1 restraint

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.65226 (6)	0.0538 (3)	0.69407 (15)	0.0236 (4)
N1	0.61387 (7)	0.6480 (3)	0.31428 (17)	0.0194 (4)
N2	0.63432 (7)	0.3591 (4)	0.49405 (16)	0.0177 (4)
C1	0.70576 (8)	0.6813 (4)	0.4124 (2)	0.0204 (4)
H1A	0.7307	0.6230	0.4781	0.025*
C2	0.72340 (9)	0.8817 (4)	0.3237 (2)	0.0212 (4)
H2A	0.7608	0.9600	0.3273	0.025*
C3	0.68583 (8)	0.9677 (4)	0.22889 (19)	0.0185 (4)
C4	0.63168 (9)	0.8438 (4)	0.2302 (2)	0.0197 (4)
H4A	0.6055	0.9022	0.1669	0.024*
C5	0.65087 (8)	0.5669 (4)	0.40364 (19)	0.0170 (4)
C6	0.70294 (9)	1.1822 (4)	0.1299 (2)	0.0228 (4)
H6A	0.6696	1.2327	0.0788	0.034*
H6B	0.7324	1.0974	0.0760	0.034*
H6C	0.7180	1.3566	0.1702	0.034*
C7	0.58560 (9)	0.2307 (4)	0.48190 (19)	0.0178 (4)
H7A	0.5619	0.2782	0.4125	0.021*
C8	0.56627 (8)	0.0167 (4)	0.57120 (18)	0.0168 (4)
C9	0.51292 (9)	−0.1140 (4)	0.5548 (2)	0.0205 (4)
H9A	0.4899	−0.0613	0.4849	0.025*
C10	0.49335 (9)	−0.3183 (4)	0.6386 (2)	0.0232 (4)
H10A	0.4570	−0.4051	0.6272	0.028*
C11	0.52755 (9)	−0.3965 (4)	0.7406 (2)	0.0222 (4)
H11A	0.5139	−0.5377	0.7981	0.027*
C12	0.58079 (9)	−0.2740 (4)	0.76055 (19)	0.0205 (4)
C13	0.60016 (8)	−0.0652 (4)	0.67508 (19)	0.0181 (4)
C14	0.61778 (10)	−0.3582 (5)	0.8700 (2)	0.0290 (5)
H14A	0.6269	−0.1862	0.9198	0.043*
H14B	0.6532	−0.4453	0.8388	0.043*
H14C	0.5974	−0.4980	0.9226	0.043*
H101	0.6583 (13)	0.190 (7)	0.639 (3)	0.046 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0218 (7)	0.0269 (8)	0.0221 (8)	−0.0048 (6)	−0.0036 (6)	0.0055 (7)
N1	0.0210 (8)	0.0201 (8)	0.0170 (8)	0.0000 (7)	−0.0007 (7)	0.0006 (7)
N2	0.0182 (8)	0.0172 (8)	0.0178 (8)	0.0001 (6)	0.0024 (6)	0.0005 (7)
C1	0.0190 (10)	0.0206 (9)	0.0217 (11)	−0.0005 (7)	−0.0031 (8)	0.0039 (8)
C2	0.0204 (9)	0.0210 (9)	0.0222 (10)	−0.0015 (8)	0.0014 (8)	0.0014 (9)
C3	0.0233 (10)	0.0163 (9)	0.0159 (9)	0.0013 (7)	0.0029 (7)	−0.0011 (8)
C4	0.0234 (10)	0.0186 (9)	0.0170 (9)	0.0021 (7)	−0.0009 (8)	0.0006 (8)
C5	0.0211 (9)	0.0148 (9)	0.0150 (9)	0.0005 (7)	0.0013 (7)	−0.0003 (7)
C6	0.0288 (11)	0.0200 (10)	0.0196 (10)	0.0007 (8)	0.0037 (8)	0.0039 (8)
C7	0.0197 (9)	0.0168 (8)	0.0169 (10)	0.0018 (7)	0.0016 (7)	−0.0009 (8)
C8	0.0184 (9)	0.0165 (8)	0.0156 (10)	0.0020 (7)	0.0023 (7)	−0.0006 (7)
C9	0.0199 (10)	0.0195 (9)	0.0222 (10)	0.0016 (7)	0.0009 (8)	−0.0015 (8)
C10	0.0190 (9)	0.0224 (10)	0.0281 (11)	−0.0001 (8)	0.0034 (8)	−0.0007 (9)
C11	0.0268 (10)	0.0183 (9)	0.0217 (11)	0.0008 (8)	0.0081 (8)	0.0008 (8)
C12	0.0248 (10)	0.0209 (10)	0.0158 (10)	0.0022 (8)	0.0030 (8)	0.0014 (8)
C13	0.0195 (9)	0.0183 (8)	0.0164 (10)	0.0012 (7)	0.0014 (7)	−0.0025 (8)
C14	0.0349 (12)	0.0318 (12)	0.0202 (11)	−0.0005 (9)	−0.0005 (9)	0.0069 (10)

Geometric parameters (Å, º)

O1—C13	1.355 (2)	C6—H6C	0.9800
O1—H101	0.87 (4)	C7—C8	1.446 (3)
N1—C4	1.341 (3)	C7—H7A	0.9500
N1—C5	1.341 (3)	C8—C9	1.401 (3)
N2—C7	1.294 (3)	C8—C13	1.413 (3)
N2—C5	1.415 (2)	C9—C10	1.379 (3)
C1—C2	1.387 (3)	C9—H9A	0.9500
C1—C5	1.395 (3)	C10—C11	1.397 (3)
C1—H1A	0.9500	C10—H10A	0.9500
C2—C3	1.397 (3)	C11—C12	1.387 (3)
C2—H2A	0.9500	C11—H11A	0.9500
C3—C4	1.393 (3)	C12—C13	1.403 (3)
C3—C6	1.503 (3)	C12—C14	1.503 (3)
C4—H4A	0.9500	C14—H14A	0.9800
C6—H6A	0.9800	C14—H14B	0.9800
C6—H6B	0.9800	C14—H14C	0.9800
C13—O1—H101	110 (2)	C8—C7—H7A	119.1
C4—N1—C5	117.50 (17)	C9—C8—C13	118.92 (17)
C7—N2—C5	119.12 (17)	C9—C8—C7	119.61 (18)
C2—C1—C5	118.93 (19)	C13—C8—C7	121.47 (17)
C2—C1—H1A	120.5	C10—C9—C8	120.8 (2)
C5—C1—H1A	120.5	C10—C9—H9A	119.6
C1—C2—C3	119.62 (18)	C8—C9—H9A	119.6
C1—C2—H2A	120.2	C9—C10—C11	119.32 (19)
C3—C2—H2A	120.2	C9—C10—H10A	120.3
C4—C3—C2	116.74 (18)	C11—C10—H10A	120.3
C4—C3—C6	121.49 (18)	C12—C11—C10	121.93 (19)
C2—C3—C6	121.77 (18)	C12—C11—H11A	119.0
N1—C4—C3	124.66 (19)	C10—C11—H11A	119.0
N1—C4—H4A	117.7	C11—C12—C13	118.30 (19)
C3—C4—H4A	117.7	C11—C12—C14	122.09 (19)
N1—C5—C1	122.52 (18)	C13—C12—C14	119.61 (19)
N1—C5—N2	119.71 (17)	O1—C13—C12	118.38 (18)
C1—C5—N2	117.77 (18)	O1—C13—C8	120.94 (17)
C3—C6—H6A	109.5	C12—C13—C8	120.67 (17)
C3—C6—H6B	109.5	C12—C14—H14A	109.5
H6A—C6—H6B	109.5	C12—C14—H14B	109.5
C3—C6—H6C	109.5	H14A—C14—H14B	109.5
H6A—C6—H6C	109.5	C12—C14—H14C	109.5
H6B—C6—H6C	109.5	H14A—C14—H14C	109.5
N2—C7—C8	121.73 (18)	H14B—C14—H14C	109.5
N2—C7—H7A	119.1
C5—C1—C2—C3	0.9 (3)	C13—C8—C9—C10	0.4 (3)
C1—C2—C3—C4	0.2 (3)	C7—C8—C9—C10	−179.86 (18)
C1—C2—C3—C6	−179.50 (18)	C8—C9—C10—C11	−0.5 (3)
C5—N1—C4—C3	0.2 (3)	C9—C10—C11—C12	0.2 (3)
C2—C3—C4—N1	−0.8 (3)	C10—C11—C12—C13	0.2 (3)
C6—C3—C4—N1	178.89 (19)	C10—C11—C12—C14	−179.8 (2)
C4—N1—C5—C1	1.0 (3)	C11—C12—C13—O1	−179.71 (18)
C4—N1—C5—N2	−179.48 (17)	C14—C12—C13—O1	0.3 (3)
C2—C1—C5—N1	−1.6 (3)	C11—C12—C13—C8	−0.3 (3)
C2—C1—C5—N2	178.90 (18)	C14—C12—C13—C8	179.73 (18)
C7—N2—C5—N1	6.5 (3)	C9—C8—C13—O1	179.42 (17)
C7—N2—C5—C1	−174.01 (18)	C7—C8—C13—O1	−0.3 (3)
C5—N2—C7—C8	−179.94 (17)	C9—C8—C13—C12	0.0 (3)
N2—C7—C8—C9	179.30 (18)	C7—C8—C13—C12	−179.77 (18)
N2—C7—C8—C13	−0.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H101···N2	0.87 (3)	1.82 (3)	2.590 (2)	146 (3)
C2—H2A···O1^i	0.95	2.52	3.322 (3)	142

Symmetry code: (i) −x+3/2, y+1, z−1/2.