(E)-4-[4-(Dimethyl-amino)benzyl-ideneamino]benzonitrile.

The mol-ecule of the title compound, C(16)H(15)N(3), displays a trans configuration with respect to the C=N double bond. The mol-ecule is not planar, the dihedral angle between the benzene rings being 57.83 (9)°. The crystal packing is stabilized only by van der Waals inter-actions.

Related literature

For the pharmacological activity of Schiff base compounds, see: Zhou et al. (2000 ▶); Sriram et al. (2006 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H15N3

M = 249.31

Monoclinic,

a = 9.733 (6) Å

b = 16.159 (9) Å

c = 9.103 (6) Å

β = 110.644 (12)°

V = 1339.8 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.985, T max = 0.985

13048 measured reflections

2610 independent reflections

2134 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.221

S = 1.09

2610 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809047023/rz2389sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047023/rz2389Isup2.hkl

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

C16H15N3	F(000) = 528
Mr = 249.31	Dx = 1.236 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3347 reflections
a = 9.733 (6) Å	θ = 2.2–27.5°
b = 16.159 (9) Å	µ = 0.08 mm−1
c = 9.103 (6) Å	T = 293 K
β = 110.644 (12)°	Block, yellow
V = 1339.8 (14) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	2610 independent reflections
Radiation source: fine-focus sealed tube	2134 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 2.2°
ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −19→19
Tmin = 0.985, Tmax = 0.985	l = −11→11
13048 measured reflections

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.1227P)2 + 0.7975P] where P = (Fo2 + 2Fc2)/3
2610 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.36 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
N2	0.9054 (2)	0.11253 (12)	0.0481 (2)	0.0259 (5)
N1	1.3132 (2)	0.12345 (13)	0.7796 (2)	0.0266 (5)
C4	1.2390 (3)	0.13388 (14)	0.6221 (3)	0.0224 (5)
C14	0.7447 (3)	0.19677 (16)	−0.3581 (3)	0.0279 (6)
H14A	0.7262	0.2472	−0.4105	0.033*
C15	0.8167 (3)	0.19445 (15)	−0.1968 (3)	0.0254 (5)
H15A	0.8479	0.2435	−0.1415	0.030*
C9	1.0202 (3)	0.15527 (14)	0.1238 (3)	0.0246 (5)
H9A	1.0606	0.1897	0.0678	0.030*
C10	0.8427 (2)	0.11873 (14)	−0.1164 (3)	0.0222 (5)
C12	0.7285 (3)	0.04706 (15)	−0.3620 (3)	0.0278 (6)
H12A	0.7008	−0.0022	−0.4174	0.033*
C11	0.7979 (3)	0.04566 (15)	−0.2013 (3)	0.0280 (6)
H11A	0.8151	−0.0048	−0.1487	0.034*
C6	1.0225 (3)	0.11201 (14)	0.3895 (3)	0.0247 (5)
H6A	0.9282	0.0907	0.3439	0.030*
C16	0.6232 (3)	0.12454 (17)	−0.6090 (3)	0.0344 (6)
C13	0.7000 (3)	0.12305 (15)	−0.4417 (3)	0.0264 (6)
C5	1.0934 (3)	0.10420 (15)	0.5487 (3)	0.0249 (5)
H5A	1.0456	0.0792	0.6092	0.030*
C2	1.2299 (3)	0.18366 (15)	0.3669 (3)	0.0260 (6)
H2B	1.2749	0.2115	0.3066	0.031*
C3	1.3042 (3)	0.17532 (15)	0.5260 (3)	0.0265 (6)
H3A	1.3983	0.1971	0.5708	0.032*
C1	1.0889 (3)	0.15156 (14)	0.2934 (3)	0.0235 (5)
N3	0.5616 (3)	0.12575 (18)	−0.7415 (3)	0.0523 (8)
C8	1.2478 (3)	0.0794 (2)	0.8776 (3)	0.0427 (7)
H8A	1.1447	0.0721	0.8211	0.064*
H8B	1.2615	0.1108	0.9713	0.064*
H8C	1.2939	0.0263	0.9053	0.064*
C7	1.4701 (3)	0.14047 (19)	0.8465 (3)	0.0350 (6)
H7A	1.5001	0.1699	0.7713	0.052*
H7B	1.5231	0.0892	0.8729	0.052*
H7C	1.4904	0.1735	0.9395	0.052*

	U11	U22	U33	U12	U13	U23
N2	0.0267 (10)	0.0271 (10)	0.0214 (10)	0.0019 (8)	0.0054 (9)	0.0007 (8)
N1	0.0246 (11)	0.0340 (12)	0.0196 (10)	−0.0042 (8)	0.0058 (8)	−0.0022 (8)
C4	0.0236 (12)	0.0212 (11)	0.0222 (11)	0.0013 (9)	0.0078 (9)	−0.0028 (9)
C14	0.0284 (13)	0.0287 (13)	0.0262 (13)	0.0007 (10)	0.0090 (10)	0.0048 (10)
C15	0.0266 (12)	0.0251 (12)	0.0238 (12)	−0.0028 (9)	0.0080 (10)	−0.0008 (9)
C9	0.0244 (12)	0.0227 (12)	0.0263 (12)	0.0026 (9)	0.0084 (10)	0.0023 (9)
C10	0.0184 (11)	0.0278 (12)	0.0203 (11)	0.0004 (9)	0.0067 (9)	0.0014 (9)
C12	0.0284 (13)	0.0276 (13)	0.0268 (13)	0.0012 (10)	0.0091 (10)	−0.0042 (10)
C11	0.0308 (13)	0.0245 (12)	0.0275 (13)	0.0066 (10)	0.0087 (10)	0.0037 (9)
C6	0.0199 (11)	0.0263 (12)	0.0269 (12)	−0.0012 (9)	0.0071 (10)	−0.0025 (9)
C16	0.0346 (14)	0.0389 (15)	0.0283 (15)	0.0001 (11)	0.0093 (12)	−0.0003 (11)
C13	0.0234 (12)	0.0340 (14)	0.0220 (12)	0.0031 (10)	0.0083 (10)	0.0018 (9)
C5	0.0251 (12)	0.0266 (12)	0.0246 (12)	−0.0018 (9)	0.0109 (10)	−0.0020 (9)
C2	0.0261 (12)	0.0252 (12)	0.0276 (12)	−0.0024 (10)	0.0103 (10)	0.0031 (9)
C3	0.0232 (12)	0.0279 (12)	0.0258 (12)	−0.0052 (9)	0.0055 (10)	−0.0016 (9)
C1	0.0244 (12)	0.0211 (11)	0.0237 (12)	0.0017 (9)	0.0066 (10)	−0.0011 (9)
N3	0.0589 (18)	0.0662 (19)	0.0246 (13)	−0.0025 (14)	0.0058 (12)	−0.0003 (11)
C8	0.0412 (16)	0.063 (2)	0.0232 (13)	−0.0160 (14)	0.0105 (12)	0.0014 (12)
C7	0.0250 (13)	0.0527 (17)	0.0237 (12)	−0.0017 (11)	0.0042 (10)	−0.0014 (11)

N2—C9	1.288 (3)	C11—H11A	0.9300
N2—C10	1.408 (3)	C6—C5	1.374 (3)
N1—C4	1.370 (3)	C6—C1	1.411 (3)
N1—C8	1.452 (3)	C6—H6A	0.9300
N1—C7	1.457 (3)	C16—N3	1.143 (4)
C4—C3	1.417 (3)	C16—C13	1.441 (3)
C4—C5	1.420 (3)	C5—H5A	0.9300
C14—C15	1.387 (3)	C2—C3	1.379 (3)
C14—C13	1.398 (4)	C2—C1	1.397 (3)
C14—H14A	0.9300	C2—H2B	0.9300
C15—C10	1.402 (3)	C3—H3A	0.9300
C15—H15A	0.9300	C8—H8A	0.9600
C9—C1	1.451 (3)	C8—H8B	0.9600
C9—H9A	0.9300	C8—H8C	0.9600
C10—C11	1.394 (3)	C7—H7A	0.9600
C12—C11	1.378 (3)	C7—H7B	0.9600
C12—C13	1.403 (3)	C7—H7C	0.9600
C12—H12A	0.9300
C9—N2—C10	120.0 (2)	N3—C16—C13	179.6 (3)
C4—N1—C8	121.3 (2)	C14—C13—C12	119.8 (2)
C4—N1—C7	120.2 (2)	C14—C13—C16	120.5 (2)
C8—N1—C7	117.2 (2)	C12—C13—C16	119.7 (2)
N1—C4—C3	121.3 (2)	C6—C5—C4	120.8 (2)
N1—C4—C5	121.4 (2)	C6—C5—H5A	119.6
C3—C4—C5	117.3 (2)	C4—C5—H5A	119.6
C15—C14—C13	119.8 (2)	C3—C2—C1	122.0 (2)
C15—C14—H14A	120.1	C3—C2—H2B	119.0
C13—C14—H14A	120.1	C1—C2—H2B	119.0
C14—C15—C10	120.4 (2)	C2—C3—C4	120.7 (2)
C14—C15—H15A	119.8	C2—C3—H3A	119.6
C10—C15—H15A	119.8	C4—C3—H3A	119.6
N2—C9—C1	122.3 (2)	C2—C1—C6	117.3 (2)
N2—C9—H9A	118.9	C2—C1—C9	120.0 (2)
C1—C9—H9A	118.9	C6—C1—C9	122.6 (2)
C11—C10—C15	119.1 (2)	N1—C8—H8A	109.5
C11—C10—N2	117.6 (2)	N1—C8—H8B	109.5
C15—C10—N2	123.2 (2)	H8A—C8—H8B	109.5
C11—C12—C13	119.8 (2)	N1—C8—H8C	109.5
C11—C12—H12A	120.1	H8A—C8—H8C	109.5
C13—C12—H12A	120.1	H8B—C8—H8C	109.5
C12—C11—C10	121.0 (2)	N1—C7—H7A	109.5
C12—C11—H11A	119.5	N1—C7—H7B	109.5
C10—C11—H11A	119.5	H7A—C7—H7B	109.5
C5—C6—C1	121.7 (2)	N1—C7—H7C	109.5
C5—C6—H6A	119.1	H7A—C7—H7C	109.5
C1—C6—H6A	119.1	H7B—C7—H7C	109.5