N-[4-(Di-methyl-amino)-benzyl-idene]-4-methyl-aniline.

The mol-ecules of the title compound, C16H18N2, exists in a trans conformation with respect to the C=N bond [1.270 (3) Å]. The least-squares plane of the di-methyl-amino group makes a dihedral angle of 1.3 (2)° with the ring to which it is attached. The dihedral angle between the two aromatic rings is 11.70 (2)°. The crystal structure features weak C-H⋯π inter-actions.

Related literature

For the uses and biological importance of diketones, see: Xia et al. (2009 ▶); Shah et al. (1992 ▶); Ünver et al. (2004 ▶). For related structures, see: Fun et al. (2011 ▶); Khalaji & Simpson (2009 ▶).

Experimental

Crystal data

C16H18N2

M = 238.32

Orthorhombic,

a = 10.4814 (10) Å

b = 8.0528 (8) Å

c = 32.571 (3) Å

V = 2749.1 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.980, T max = 0.987

17121 measured reflections

2692 independent reflections

1737 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.187

S = 1.08

2692 reflections

167 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681301249X/bt6904sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301249X/bt6904Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301249X/bt6904Isup3.cml

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

C16H18N2	F(000) = 1024
Mr = 238.32	Dx = 1.152 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1737 reflections
a = 10.4814 (10) Å	θ = 2.3–26.0°
b = 8.0528 (8) Å	µ = 0.07 mm−1
c = 32.571 (3) Å	T = 296 K
V = 2749.1 (4) Å3	Block, yellow
Z = 8	0.30 × 0.25 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	2692 independent reflections
Radiation source: fine-focus sealed tube	1737 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ω and φ scan	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
Tmin = 0.980, Tmax = 0.987	k = −9→7
17121 measured reflections	l = −40→40

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061	H-atom parameters constrained
wR(F2) = 0.187	w = 1/[σ2(Fo2) + (0.0814P)2 + 0.8121P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2692 reflections	Δρmax = 0.21 e Å−3
167 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0130 (19)

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
C6	0.0030 (3)	0.4888 (3)	0.18005 (8)	0.0768 (8)
H6	−0.0658	0.5293	0.1651	0.092*
C14	0.0373 (2)	0.2889 (2)	0.03147 (7)	0.0523 (6)
H14	−0.0182	0.3671	0.0425	0.063*
C13	0.0307 (2)	0.2534 (3)	−0.00941 (7)	0.0528 (6)
H13	−0.0297	0.3073	−0.0255	0.063*
C15	0.1898 (3)	−0.0172 (4)	−0.08750 (8)	0.0805 (8)
H15A	0.2757	0.0243	−0.0875	0.121*
H15B	0.1629	−0.0378	−0.1152	0.121*
H15C	0.1862	−0.1187	−0.0721	0.121*
C16	0.0139 (3)	0.1841 (4)	−0.09499 (8)	0.0809 (8)
H16A	−0.0705	0.1568	−0.0857	0.121*
H16B	0.0247	0.1468	−0.1228	0.121*
H16C	0.0258	0.3022	−0.0938	0.121*
C10	0.2053 (2)	0.0940 (2)	0.03889 (7)	0.0530 (6)
H10	0.2640	0.0380	0.0552	0.064*
C1	0.1192 (4)	0.5064 (5)	0.29002 (9)	0.1148 (13)
H1A	0.1367	0.6223	0.2939	0.172*
H1B	0.1863	0.4416	0.3021	0.172*
H1C	0.0395	0.4787	0.3029	0.172*
C3	0.2043 (3)	0.3782 (4)	0.22509 (9)	0.0862 (9)
H3	0.2737	0.3400	0.2402	0.103*
C7	0.0115 (3)	0.5248 (4)	0.22110 (9)	0.0831 (9)
H7	−0.0521	0.5886	0.2333	0.100*
C4	0.1978 (3)	0.3420 (4)	0.18370 (8)	0.0788 (8)
H4	0.2632	0.2823	0.1713	0.095*
C2	0.1112 (3)	0.4694 (3)	0.24474 (8)	0.0791 (8)
C9	0.1257 (2)	0.2105 (2)	0.05712 (7)	0.0482 (5)
C12	0.11276 (19)	0.1375 (2)	−0.02776 (7)	0.0477 (5)
C5	0.0941 (2)	0.3941 (3)	0.16042 (7)	0.0607 (6)
N2	0.10664 (19)	0.1037 (2)	−0.06899 (6)	0.0632 (6)
N1	0.0775 (2)	0.3645 (2)	0.11798 (6)	0.0630 (6)
C11	0.2007 (2)	0.0582 (2)	−0.00217 (7)	0.0527 (6)
H11	0.2567	−0.0197	−0.0131	0.063*
C8	0.1356 (2)	0.2458 (3)	0.10037 (7)	0.0541 (6)
H22E	0.1874	0.1778	0.1163	0.065*

	U11	U22	U33	U12	U13	U23
C6	0.0832 (19)	0.0809 (18)	0.0664 (17)	0.0181 (15)	0.0077 (14)	0.0081 (14)
C14	0.0464 (12)	0.0402 (11)	0.0703 (15)	0.0053 (9)	0.0058 (11)	0.0021 (10)
C13	0.0470 (13)	0.0445 (11)	0.0669 (14)	0.0029 (9)	−0.0055 (11)	0.0087 (10)
C15	0.0811 (19)	0.0882 (19)	0.0721 (16)	0.0062 (15)	0.0070 (15)	−0.0134 (14)
C16	0.099 (2)	0.0781 (18)	0.0657 (16)	0.0016 (15)	−0.0108 (15)	0.0086 (13)
C10	0.0463 (13)	0.0431 (11)	0.0696 (14)	0.0046 (9)	−0.0046 (11)	0.0095 (10)
C1	0.147 (3)	0.132 (3)	0.0655 (18)	−0.002 (3)	0.001 (2)	−0.0060 (18)
C3	0.094 (2)	0.091 (2)	0.0741 (18)	0.0121 (17)	−0.0165 (16)	−0.0009 (15)
C7	0.092 (2)	0.085 (2)	0.0722 (18)	0.0140 (16)	0.0183 (17)	0.0006 (15)
C4	0.077 (2)	0.0833 (19)	0.0759 (17)	0.0150 (15)	−0.0038 (15)	−0.0099 (14)
C2	0.103 (2)	0.0753 (18)	0.0593 (16)	−0.0054 (16)	0.0072 (16)	0.0052 (13)
C9	0.0459 (12)	0.0381 (11)	0.0607 (13)	−0.0047 (8)	0.0043 (10)	0.0078 (9)
C12	0.0422 (12)	0.0411 (11)	0.0597 (13)	−0.0066 (8)	0.0038 (10)	0.0035 (9)
C5	0.0697 (17)	0.0530 (13)	0.0592 (14)	0.0018 (11)	0.0053 (12)	0.0076 (11)
N2	0.0613 (13)	0.0650 (12)	0.0632 (12)	0.0064 (10)	−0.0013 (10)	0.0009 (10)
N1	0.0684 (14)	0.0608 (12)	0.0599 (12)	0.0050 (10)	0.0046 (10)	0.0042 (9)
C11	0.0443 (13)	0.0429 (11)	0.0710 (14)	0.0051 (9)	0.0024 (11)	0.0004 (10)
C8	0.0524 (13)	0.0428 (12)	0.0670 (14)	−0.0018 (9)	0.0016 (11)	0.0110 (10)

C6—C7	1.371 (4)	C1—C2	1.507 (4)
C6—C5	1.378 (3)	C1—H1A	0.9600
C6—H6	0.9300	C1—H1B	0.9600
C14—C13	1.364 (3)	C1—H1C	0.9600
C14—C9	1.398 (3)	C3—C2	1.379 (4)
C14—H14	0.9300	C3—C4	1.381 (4)
C13—C12	1.403 (3)	C3—H3	0.9300
C13—H13	0.9300	C7—C2	1.373 (4)
C15—N2	1.439 (3)	C7—H7	0.9300
C15—H15A	0.9600	C4—C5	1.390 (3)
C15—H15B	0.9600	C4—H4	0.9300
C15—H15C	0.9600	C9—C8	1.441 (3)
C16—N2	1.443 (3)	C12—N2	1.372 (3)
C16—H16A	0.9600	C12—C11	1.397 (3)
C16—H16B	0.9600	C5—N1	1.413 (3)
C16—H16C	0.9600	N1—C8	1.270 (3)
C10—C11	1.369 (3)	C11—H11	0.9300
C10—C9	1.389 (3)	C8—H22E	0.9300
C10—H10	0.9300
C7—C6—C5	121.6 (3)	C2—C3—H3	119.0
C7—C6—H6	119.2	C4—C3—H3	119.0
C5—C6—H6	119.2	C6—C7—C2	121.8 (3)
C13—C14—C9	121.5 (2)	C6—C7—H7	119.1
C13—C14—H14	119.3	C2—C7—H7	119.1
C9—C14—H14	119.3	C3—C4—C5	120.5 (3)
C14—C13—C12	121.6 (2)	C3—C4—H4	119.8
C14—C13—H13	119.2	C5—C4—H4	119.8
C12—C13—H13	119.2	C7—C2—C3	116.8 (3)
N2—C15—H15A	109.5	C7—C2—C1	121.8 (3)
N2—C15—H15B	109.5	C3—C2—C1	121.4 (3)
H15A—C15—H15B	109.5	C10—C9—C14	116.6 (2)
N2—C15—H15C	109.5	C10—C9—C8	120.6 (2)
H15A—C15—H15C	109.5	C14—C9—C8	122.8 (2)
H15B—C15—H15C	109.5	N2—C12—C11	121.6 (2)
N2—C16—H16A	109.5	N2—C12—C13	121.4 (2)
N2—C16—H16B	109.5	C11—C12—C13	117.1 (2)
H16A—C16—H16B	109.5	C6—C5—C4	117.1 (2)
N2—C16—H16C	109.5	C6—C5—N1	117.5 (2)
H16A—C16—H16C	109.5	C4—C5—N1	125.3 (2)
H16B—C16—H16C	109.5	C12—N2—C15	121.1 (2)
C11—C10—C9	122.6 (2)	C12—N2—C16	121.1 (2)
C11—C10—H10	118.7	C15—N2—C16	117.7 (2)
C9—C10—H10	118.7	C8—N1—C5	120.6 (2)
C2—C1—H1A	109.5	C10—C11—C12	120.6 (2)
C2—C1—H1B	109.5	C10—C11—H11	119.7
H1A—C1—H1B	109.5	C12—C11—H11	119.7
C2—C1—H1C	109.5	N1—C8—C9	123.8 (2)
H1A—C1—H1C	109.5	N1—C8—H22E	118.1
H1B—C1—H1C	109.5	C9—C8—H22E	118.1
C2—C3—C4	122.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cg1i	0.93	2.94	3.670 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cg1i	0.93	2.94	3.670 (2)	137

Symmetry code: (i) .