(E)-2,4,6-Trimethyl-N-(pyridin-2-yl-methyl-idene)aniline.

In the title compound, C(15)H(16)N(2), has an E conformation about the central N=C bond. The benzene and pyridine rings are almost normal to one another with a dihedral angle of 87.47(8)°. In the crystal, there are no classical hydrogen bonds.

Related literature

For C—N bond forming reactions, see: Alonso-Moreno et al. (2009 ▶); Qiu et al. (2009 ▶). For imino C=N bonds in a related structure, see: Nienkemper et al. (2006 ▶). For the preparation of related compounds, see: Bianchini et al. (2001 ▶); Fan et al. (2009 ▶).

Experimental

Crystal data

C15H16N2

M = 224.30

Monoclinic,

a = 8.2490 (16) Å

b = 16.136 (3) Å

c = 10.150 (2) Å

β = 104.76 (3)°

V = 1306.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.36 × 0.34 × 0.29 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.976, T max = 0.981

12591 measured reflections

2982 independent reflections

1952 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.200

S = 1.03

2982 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXP97 (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015905/zj2067sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015905/zj2067Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015905/zj2067Isup3.cml

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

C15H16N2	F(000) = 480
Mr = 224.30	Dx = 1.140 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12591 reflections
a = 8.2490 (16) Å	θ = 3.1–27.5°
b = 16.136 (3) Å	µ = 0.07 mm−1
c = 10.150 (2) Å	T = 293 K
β = 104.76 (3)°	Block, colorless
V = 1306.4 (4) Å3	0.36 × 0.34 × 0.29 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2982 independent reflections
Radiation source: fine-focus sealed tube	1952 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
phi and ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.976, Tmax = 0.981	k = −20→20
12591 measured reflections	l = −13→13

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.200	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.1315P)2] where P = (Fo2 + 2Fc2)/3
2982 reflections	(Δ/σ)max = 0.017
154 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.22 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	−0.08242 (19)	−0.04738 (10)	0.77519 (15)	0.0748 (5)
N2	0.20612 (16)	0.11712 (9)	0.82639 (12)	0.0612 (4)
C1	−0.02245 (18)	0.02378 (10)	0.74182 (15)	0.0559 (4)
C2	−0.0893 (2)	0.06280 (13)	0.61937 (16)	0.0714 (5)
H2A	−0.0460	0.1131	0.5993	0.086*
C3	−0.2097 (2)	−0.08143 (14)	0.6828 (2)	0.0830 (6)
H3A	−0.2515	−0.1318	0.7042	0.100*
C4	−0.2827 (2)	−0.04703 (15)	0.55889 (18)	0.0816 (6)
H4A	−0.3718	−0.0731	0.4983	0.098*
C5	−0.2218 (3)	0.02585 (16)	0.52670 (19)	0.0854 (6)
H5A	−0.2686	0.0509	0.4431	0.102*
C6	0.12079 (18)	0.05750 (10)	0.84678 (15)	0.0572 (4)
H6A	0.1483	0.0328	0.9324	0.069*
C7	0.34417 (17)	0.14354 (9)	0.93500 (15)	0.0529 (4)
C8	0.50580 (18)	0.11695 (10)	0.93612 (15)	0.0561 (4)
C9	0.63854 (18)	0.14503 (10)	1.04089 (16)	0.0598 (4)
H9A	0.7465	0.1274	1.0430	0.072*
C10	0.61645 (18)	0.19772 (10)	1.14131 (17)	0.0600 (4)
C11	0.45476 (19)	0.22368 (11)	1.13626 (16)	0.0611 (4)
H11A	0.4379	0.2595	1.2033	0.073*
C12	0.31661 (18)	0.19793 (10)	1.03427 (15)	0.0556 (4)
C13	0.5355 (2)	0.05931 (13)	0.82917 (18)	0.0760 (5)
H13A	0.6532	0.0479	0.8462	0.114*
H13B	0.4964	0.0846	0.7411	0.114*
H13C	0.4758	0.0085	0.8316	0.114*
C14	0.7641 (2)	0.22552 (14)	1.2553 (2)	0.0844 (6)
H14A	0.8654	0.2017	1.2422	0.127*
H14B	0.7479	0.2076	1.3413	0.127*
H14C	0.7723	0.2849	1.2546	0.127*
C15	0.1431 (2)	0.22807 (13)	1.0332 (2)	0.0755 (6)
H15A	0.1494	0.2642	1.1094	0.113*
H15B	0.0730	0.1815	1.0393	0.113*
H15C	0.0965	0.2577	0.9501	0.113*

	U11	U22	U33	U12	U13	U23
N1	0.0668 (9)	0.0740 (10)	0.0716 (9)	−0.0142 (7)	−0.0044 (7)	0.0011 (7)
N2	0.0550 (7)	0.0706 (9)	0.0494 (7)	−0.0078 (6)	−0.0024 (6)	0.0029 (6)
C1	0.0461 (7)	0.0634 (9)	0.0540 (8)	0.0000 (6)	0.0050 (6)	−0.0066 (7)
C2	0.0625 (9)	0.0853 (13)	0.0584 (9)	−0.0121 (8)	0.0006 (8)	0.0021 (8)
C3	0.0724 (11)	0.0809 (13)	0.0839 (13)	−0.0218 (9)	−0.0016 (10)	−0.0076 (10)
C4	0.0599 (10)	0.1080 (16)	0.0677 (11)	−0.0180 (10)	−0.0007 (9)	−0.0236 (11)
C5	0.0723 (12)	0.1173 (17)	0.0541 (9)	−0.0139 (11)	−0.0067 (8)	0.0006 (10)
C6	0.0515 (8)	0.0627 (9)	0.0499 (7)	−0.0020 (7)	−0.0008 (6)	0.0013 (7)
C7	0.0489 (7)	0.0565 (9)	0.0470 (7)	−0.0056 (6)	0.0006 (6)	0.0057 (6)
C8	0.0537 (8)	0.0609 (9)	0.0506 (8)	−0.0007 (7)	0.0077 (6)	0.0032 (6)
C9	0.0429 (7)	0.0695 (10)	0.0631 (9)	−0.0015 (6)	0.0062 (7)	0.0033 (7)
C10	0.0473 (8)	0.0654 (10)	0.0600 (9)	−0.0091 (7)	0.0001 (7)	−0.0011 (7)
C11	0.0556 (8)	0.0634 (10)	0.0593 (8)	−0.0052 (7)	0.0055 (7)	−0.0090 (7)
C12	0.0463 (7)	0.0590 (9)	0.0564 (8)	−0.0009 (6)	0.0038 (6)	0.0015 (7)
C13	0.0742 (11)	0.0847 (13)	0.0654 (10)	0.0051 (9)	0.0113 (9)	−0.0099 (9)
C14	0.0577 (10)	0.0992 (15)	0.0829 (12)	−0.0133 (9)	−0.0066 (9)	−0.0186 (11)
C15	0.0522 (9)	0.0831 (12)	0.0836 (12)	0.0113 (8)	0.0035 (8)	−0.0091 (10)

N1—C1	1.328 (2)	C8—C13	1.496 (2)
N1—C3	1.335 (2)	C9—C10	1.375 (2)
N2—C6	1.240 (2)	C9—H9A	0.9300
N2—C7	1.4333 (18)	C10—C11	1.386 (2)
C1—C2	1.377 (2)	C10—C14	1.518 (2)
C1—C6	1.478 (2)	C11—C12	1.393 (2)
C2—C5	1.383 (2)	C11—H11A	0.9300
C2—H2A	0.9300	C12—C15	1.509 (2)
C3—C4	1.366 (3)	C13—H13A	0.9600
C3—H3A	0.9300	C13—H13B	0.9600
C4—C5	1.351 (3)	C13—H13C	0.9600
C4—H4A	0.9300	C14—H14A	0.9600
C5—H5A	0.9300	C14—H14B	0.9600
C6—H6A	0.9300	C14—H14C	0.9600
C7—C12	1.398 (2)	C15—H15A	0.9600
C7—C8	1.398 (2)	C15—H15B	0.9600
C8—C9	1.394 (2)	C15—H15C	0.9600
C1—N1—C3	117.01 (15)	C8—C9—H9A	118.7
C6—N2—C7	118.42 (13)	C9—C10—C11	117.87 (14)
N1—C1—C2	122.42 (15)	C9—C10—C14	121.05 (15)
N1—C1—C6	114.57 (13)	C11—C10—C14	121.08 (17)
C2—C1—C6	123.01 (16)	C10—C11—C12	122.30 (16)
C1—C2—C5	118.83 (19)	C10—C11—H11A	118.8
C1—C2—H2A	120.6	C12—C11—H11A	118.8
C5—C2—H2A	120.6	C11—C12—C7	118.05 (14)
N1—C3—C4	124.2 (2)	C11—C12—C15	120.26 (16)
N1—C3—H3A	117.9	C7—C12—C15	121.68 (14)
C4—C3—H3A	117.9	C8—C13—H13A	109.5
C5—C4—C3	118.21 (16)	C8—C13—H13B	109.5
C5—C4—H4A	120.9	H13A—C13—H13B	109.5
C3—C4—H4A	120.9	C8—C13—H13C	109.5
C4—C5—C2	119.27 (17)	H13A—C13—H13C	109.5
C4—C5—H5A	120.4	H13B—C13—H13C	109.5
C2—C5—H5A	120.4	C10—C14—H14A	109.5
N2—C6—C1	123.27 (14)	C10—C14—H14B	109.5
N2—C6—H6A	118.4	H14A—C14—H14B	109.5
C1—C6—H6A	118.4	C10—C14—H14C	109.5
C12—C7—C8	121.12 (13)	H14A—C14—H14C	109.5
C12—C7—N2	119.87 (13)	H14B—C14—H14C	109.5
C8—C7—N2	118.96 (14)	C12—C15—H15A	109.5
C9—C8—C7	117.96 (15)	C12—C15—H15B	109.5
C9—C8—C13	120.92 (14)	H15A—C15—H15B	109.5
C7—C8—C13	121.12 (14)	C12—C15—H15C	109.5
C10—C9—C8	122.69 (14)	H15A—C15—H15C	109.5
C10—C9—H9A	118.7	H15B—C15—H15C	109.5