(E)-1-{6-[1-(2,6-Dimethyl-phenyl-imino)-eth-yl]pyridin-2-yl}ethanone.

In the title compound, C(17)H(18)N(2)O, the dijedral angle between the mean planes of the pyridine and benzene rings is 78.0 (1)°. In the crystal, pairs of C-H⋯O inter-actions with graph-set motif R(2) (2)(10) form inversion dimers. Adjacent dimers are further connected into a three-dimensional network by C-H⋯O connections. There is also an inter-action between the carbonyl groups in adjacent mol-ecules with an O⋯C distance of 3.176 (2) Å.

Related literature

For the synthesis of mono- and bis­(imino)­pyridine ligands and catalytic applications of their metal complexes, see: Schmidt et al. (2002 ▶); Bianchini et al. (2003 ▶); Britovsek et al. (1999 ▶); Mecking et al. (2001 ▶); Gibson et al. (2007 ▶). For graph-set analysis of hydrogen-bonded networks, see: Bernstein et al. (1995 ▶). For carbon­yl–carbonyl inter­actions, see: Allen et al. (1998 ▶).

Experimental

Crystal data

C17H18N2O

M = 266.33

Triclinic,

a = 6.2988 (13) Å

b = 7.9684 (16) Å

c = 16.009 (3) Å

α = 99.57 (3)°

β = 96.40 (3)°

γ = 108.31 (3)°

V = 740.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.48 × 0.39 × 0.21 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.965, T max = 0.984

7308 measured reflections

3359 independent reflections

2372 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.143

S = 1.06

3359 reflections

185 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.13 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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 datablock(s) global, I. DOI: 10.1107/S1600536811056327/mw2044sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811056327/mw2044Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811056327/mw2044Isup3.cml

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

C17H18N2O	Z = 2
Mr = 266.33	F(000) = 284
Triclinic, P1	Dx = 1.194 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2988 (13) Å	Cell parameters from 5656 reflections
b = 7.9684 (16) Å	θ = 3.3–27.5°
c = 16.009 (3) Å	µ = 0.08 mm−1
α = 99.57 (3)°	T = 293 K
β = 96.40 (3)°	Block, yellow
γ = 108.31 (3)°	0.48 × 0.39 × 0.21 mm
V = 740.6 (3) Å3

Rigaku R-AXIS RAPID diffractometer	3359 independent reflections
Radiation source: fine-focus sealed tube	2372 reflections with I > 2σ(I)
graphite	Rint = 0.017
ω scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→8
Tmin = 0.965, Tmax = 0.984	k = −10→10
7308 measured reflections	l = −20→20

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.080P)2 + 0.0412P] where P = (Fo2 + 2Fc2)/3
3359 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.13 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
O1	−0.1379 (2)	−0.37717 (16)	0.54963 (7)	0.0681 (3)
N1	−0.01368 (18)	−0.15963 (14)	0.37828 (7)	0.0422 (3)
N2	−0.0626 (2)	0.02226 (15)	0.19274 (7)	0.0471 (3)
C1	−0.1418 (2)	−0.27314 (17)	0.42051 (9)	0.0434 (3)
C2	−0.3694 (2)	−0.37081 (19)	0.39062 (10)	0.0531 (4)
H2	−0.4536	−0.4474	0.4220	0.064*
C3	−0.4679 (3)	−0.3518 (2)	0.31350 (11)	0.0607 (4)
H3	−0.6201	−0.4171	0.2914	0.073*
C4	−0.3396 (2)	−0.23533 (19)	0.26906 (10)	0.0524 (4)
H4	−0.4038	−0.2206	0.2168	0.063*
C5	−0.1126 (2)	−0.14023 (16)	0.30375 (8)	0.0410 (3)
C6	−0.0265 (3)	−0.28860 (19)	0.50480 (9)	0.0494 (3)
C7	0.2229 (3)	−0.1950 (2)	0.53064 (10)	0.0616 (4)
H7A	0.2725	−0.2148	0.5859	0.092*
H7B	0.2578	−0.0676	0.5338	0.092*
H7C	0.2994	−0.2421	0.4889	0.092*
C8	0.0334 (2)	−0.00400 (16)	0.26111 (8)	0.0410 (3)
C9	0.2751 (2)	0.0919 (2)	0.30375 (10)	0.0543 (4)
H9A	0.3439	0.1871	0.2753	0.081*
H9B	0.3561	0.0078	0.3003	0.081*
H9C	0.2806	0.1426	0.3630	0.081*
C10	0.0553 (2)	0.15611 (17)	0.14995 (8)	0.0445 (3)
C11	0.0037 (2)	0.31576 (18)	0.15929 (9)	0.0496 (3)
C12	0.1034 (3)	0.4428 (2)	0.11335 (11)	0.0632 (4)
H12	0.0720	0.5502	0.1193	0.076*
C13	0.2480 (3)	0.4132 (2)	0.05903 (12)	0.0746 (5)
H13	0.3128	0.4997	0.0283	0.090*
C14	0.2970 (3)	0.2554 (3)	0.05017 (12)	0.0724 (5)
H14	0.3953	0.2366	0.0133	0.087*
C15	0.2030 (3)	0.1238 (2)	0.09492 (9)	0.0545 (4)
C16	−0.1539 (3)	0.3483 (2)	0.21889 (13)	0.0713 (5)
H16A	−0.0827	0.3648	0.2773	0.107*
H16B	−0.2920	0.2460	0.2060	0.107*
H16C	−0.1879	0.4547	0.2114	0.107*
C17	0.2582 (4)	−0.0483 (2)	0.08336 (12)	0.0711 (5)
H17A	0.2760	−0.0826	0.0249	0.107*
H17B	0.1370	−0.1427	0.0966	0.107*
H17C	0.3968	−0.0294	0.1212	0.107*

	U11	U22	U33	U12	U13	U23
O1	0.0754 (8)	0.0750 (7)	0.0612 (6)	0.0197 (6)	0.0261 (6)	0.0361 (6)
N1	0.0402 (6)	0.0407 (6)	0.0481 (6)	0.0116 (5)	0.0132 (5)	0.0164 (5)
N2	0.0446 (6)	0.0447 (6)	0.0520 (6)	0.0100 (5)	0.0094 (5)	0.0201 (5)
C1	0.0459 (7)	0.0389 (6)	0.0500 (7)	0.0144 (6)	0.0172 (6)	0.0162 (5)
C2	0.0467 (8)	0.0496 (8)	0.0653 (9)	0.0088 (6)	0.0208 (7)	0.0255 (7)
C3	0.0391 (8)	0.0600 (9)	0.0748 (10)	0.0014 (6)	0.0079 (7)	0.0239 (8)
C4	0.0440 (8)	0.0520 (8)	0.0586 (8)	0.0087 (6)	0.0061 (6)	0.0217 (7)
C5	0.0396 (7)	0.0381 (6)	0.0473 (7)	0.0121 (5)	0.0119 (5)	0.0140 (5)
C6	0.0586 (9)	0.0457 (7)	0.0500 (7)	0.0195 (6)	0.0178 (6)	0.0174 (6)
C7	0.0593 (10)	0.0645 (9)	0.0594 (9)	0.0157 (8)	0.0052 (7)	0.0225 (7)
C8	0.0399 (7)	0.0380 (6)	0.0467 (7)	0.0116 (5)	0.0121 (5)	0.0133 (5)
C9	0.0433 (8)	0.0586 (8)	0.0565 (8)	0.0048 (6)	0.0096 (6)	0.0236 (7)
C10	0.0421 (7)	0.0430 (7)	0.0462 (7)	0.0081 (6)	0.0054 (6)	0.0177 (6)
C11	0.0490 (8)	0.0449 (7)	0.0533 (8)	0.0125 (6)	0.0049 (6)	0.0155 (6)
C12	0.0712 (11)	0.0462 (8)	0.0739 (10)	0.0168 (7)	0.0091 (8)	0.0255 (7)
C13	0.0807 (13)	0.0666 (11)	0.0852 (12)	0.0158 (9)	0.0293 (10)	0.0481 (9)
C14	0.0790 (12)	0.0786 (11)	0.0771 (11)	0.0297 (10)	0.0398 (10)	0.0411 (9)
C15	0.0587 (9)	0.0548 (8)	0.0557 (8)	0.0198 (7)	0.0171 (7)	0.0221 (7)
C16	0.0746 (12)	0.0665 (10)	0.0844 (12)	0.0338 (9)	0.0261 (9)	0.0204 (9)
C17	0.0866 (13)	0.0702 (11)	0.0733 (11)	0.0400 (10)	0.0308 (9)	0.0236 (9)

O1—C6	1.2147 (17)	C9—H9B	0.9600
N1—C5	1.3386 (18)	C9—H9C	0.9600
N1—C1	1.3388 (16)	C10—C11	1.3977 (19)
N2—C8	1.2712 (17)	C10—C15	1.4022 (19)
N2—C10	1.4202 (16)	C11—C12	1.382 (2)
C1—C2	1.383 (2)	C11—C16	1.501 (2)
C1—C6	1.502 (2)	C12—C13	1.373 (3)
C2—C3	1.372 (2)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.375 (3)
C3—C4	1.377 (2)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.384 (2)
C4—C5	1.389 (2)	C14—H14	0.9300
C4—H4	0.9300	C15—C17	1.506 (2)
C5—C8	1.4997 (17)	C16—H16A	0.9600
C6—C7	1.487 (2)	C16—H16B	0.9600
C7—H7A	0.9600	C16—H16C	0.9600
C7—H7B	0.9600	C17—H17A	0.9600
C7—H7C	0.9600	C17—H17B	0.9600
C8—C9	1.494 (2)	C17—H17C	0.9600
C9—H9A	0.9600
C5—N1—C1	117.90 (12)	H9A—C9—H9C	109.5
C8—N2—C10	121.37 (12)	H9B—C9—H9C	109.5
N1—C1—C2	123.17 (13)	C11—C10—C15	121.17 (12)
N1—C1—C6	116.46 (12)	C11—C10—N2	117.17 (12)
C2—C1—C6	120.37 (12)	C15—C10—N2	121.46 (12)
C3—C2—C1	118.35 (13)	C12—C11—C10	118.41 (14)
C3—C2—H2	120.8	C12—C11—C16	121.22 (14)
C1—C2—H2	120.8	C10—C11—C16	120.37 (13)
C2—C3—C4	119.49 (14)	C13—C12—C11	121.19 (15)
C2—C3—H3	120.3	C13—C12—H12	119.4
C4—C3—H3	120.3	C11—C12—H12	119.4
C3—C4—C5	118.80 (14)	C12—C13—C14	119.88 (14)
C3—C4—H4	120.6	C12—C13—H13	120.1
C5—C4—H4	120.6	C14—C13—H13	120.1
N1—C5—C4	122.27 (12)	C13—C14—C15	121.44 (15)
N1—C5—C8	116.15 (12)	C13—C14—H14	119.3
C4—C5—C8	121.54 (12)	C15—C14—H14	119.3
O1—C6—C7	121.86 (14)	C14—C15—C10	117.91 (14)
O1—C6—C1	119.54 (14)	C14—C15—C17	120.26 (14)
C7—C6—C1	118.60 (12)	C10—C15—C17	121.82 (13)
C6—C7—H7A	109.5	C11—C16—H16A	109.5
C6—C7—H7B	109.5	C11—C16—H16B	109.5
H7A—C7—H7B	109.5	H16A—C16—H16B	109.5
C6—C7—H7C	109.5	C11—C16—H16C	109.5
H7A—C7—H7C	109.5	H16A—C16—H16C	109.5
H7B—C7—H7C	109.5	H16B—C16—H16C	109.5
N2—C8—C9	125.99 (12)	C15—C17—H17A	109.5
N2—C8—C5	116.51 (12)	C15—C17—H17B	109.5
C9—C8—C5	117.47 (12)	H17A—C17—H17B	109.5
C8—C9—H9A	109.5	C15—C17—H17C	109.5
C8—C9—H9B	109.5	H17A—C17—H17C	109.5
H9A—C9—H9B	109.5	H17B—C17—H17C	109.5
C8—C9—H9C	109.5
C5—N1—C1—C2	0.26 (19)	N1—C5—C8—C9	1.94 (17)
C5—N1—C1—C6	−178.75 (11)	C4—C5—C8—C9	179.65 (12)
N1—C1—C2—C3	0.7 (2)	C8—N2—C10—C11	−104.44 (15)
C6—C1—C2—C3	179.71 (13)	C8—N2—C10—C15	80.74 (18)
C1—C2—C3—C4	−0.9 (2)	C15—C10—C11—C12	−0.5 (2)
C2—C3—C4—C5	0.2 (2)	N2—C10—C11—C12	−175.34 (13)
C1—N1—C5—C4	−1.06 (19)	C15—C10—C11—C16	−179.67 (15)
C1—N1—C5—C8	176.62 (10)	N2—C10—C11—C16	5.5 (2)
C3—C4—C5—N1	0.9 (2)	C10—C11—C12—C13	0.7 (2)
C3—C4—C5—C8	−176.71 (12)	C16—C11—C12—C13	179.82 (18)
N1—C1—C6—O1	173.71 (12)	C11—C12—C13—C14	−0.5 (3)
C2—C1—C6—O1	−5.3 (2)	C12—C13—C14—C15	0.1 (3)
N1—C1—C6—C7	−6.63 (18)	C13—C14—C15—C10	0.0 (3)
C2—C1—C6—C7	174.33 (13)	C13—C14—C15—C17	179.49 (18)
C10—N2—C8—C9	−2.1 (2)	C11—C10—C15—C14	0.2 (2)
C10—N2—C8—C5	176.01 (11)	N2—C10—C15—C14	174.78 (15)
N1—C5—C8—N2	−176.33 (11)	C11—C10—C15—C17	−179.28 (15)
C4—C5—C8—N2	1.38 (18)	N2—C10—C15—C17	−4.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.64	3.459 (2)	147
C9—H9C···O1ii	0.96	2.59	3.366 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.64	3.459 (2)	147
C9—H9C⋯O1ii	0.96	2.59	3.366 (2)	138

Symmetry codes: (i) ; (ii) .