3-[4-(Dimethyl-amino)benzyl-ideneamino]benzonitrile.

The mol-ecule of the title Schiff base, C(16)H(15)N(3), is non-planar and displays a trans configuration with respect to the C=N double bond. The two benzene rings make a dihedral angle of 49.24 (3)°.

Related literature

For general background on Schiff base coordination complexes, see: Garnovskii et al. (1993 ▶). For a related structure, see: Gong & Xu (2008 ▶)

Experimental

Crystal data

C16H15N3

M = 249.31

Monoclinic,

a = 6.0924 (6) Å

b = 29.127 (3) Å

c = 7.3768 (7) Å

β = 92.924 (1)°

V = 1307.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.961, T max = 1.000 (expected range = 0.947–0.985)

7018 measured reflections

2559 independent reflections

2241 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.110

S = 1.05

2559 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.25 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011568/dn2436sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011568/dn2436Isup2.hkl

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

C16H15N3	F(000) = 528
Mr = 249.31	Dx = 1.267 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2559 reflections
a = 6.0924 (6) Å	θ = 2.8–26.0°
b = 29.127 (3) Å	µ = 0.08 mm−1
c = 7.3768 (7) Å	T = 293 K
β = 92.924 (1)°	Block, yellow
V = 1307.3 (2) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2559 independent reflections
Radiation source: fine-focus sealed tube	2241 reflections with I > 2σ(I)
graphite	Rint = 0.064
φ and ω scans	θmax = 26.0°, θmin = 2.8°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −7→7
Tmin = 0.961, Tmax = 1.000	k = −35→25
7018 measured reflections	l = −9→8

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.1755P] where P = (Fo2 + 2Fc2)/3
2559 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.25 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	0.61108 (15)	0.27979 (3)	0.59956 (13)	0.0190 (2)
N2	0.28428 (16)	0.47022 (3)	0.70360 (14)	0.0263 (3)
N3	0.14557 (15)	0.08098 (3)	0.61116 (13)	0.0189 (2)
C1	0.65373 (17)	0.32723 (4)	0.58571 (14)	0.0171 (2)
C2	0.50894 (17)	0.36071 (4)	0.64200 (14)	0.0169 (2)
H2A	0.3790	0.3523	0.6941	0.020*
C3	0.56051 (17)	0.40708 (4)	0.61955 (14)	0.0175 (3)
C4	0.75672 (18)	0.42049 (4)	0.54437 (14)	0.0190 (3)
H4A	0.7889	0.4514	0.5285	0.023*
C5	0.90207 (18)	0.38678 (4)	0.49403 (15)	0.0207 (3)
H5A	1.0341	0.3951	0.4452	0.025*
C6	0.85265 (17)	0.34081 (4)	0.51572 (15)	0.0197 (3)
H6A	0.9532	0.3186	0.4833	0.024*
C7	0.40682 (18)	0.44200 (4)	0.66975 (15)	0.0198 (3)
C8	0.42252 (17)	0.26531 (4)	0.53867 (14)	0.0174 (3)
H8A	0.3245	0.2863	0.4847	0.021*
C9	0.35526 (17)	0.21769 (4)	0.55017 (14)	0.0171 (3)
C10	0.14627 (17)	0.20363 (4)	0.48467 (15)	0.0188 (3)
H10A	0.0515	0.2251	0.4298	0.023*
C11	0.07713 (17)	0.15861 (4)	0.49941 (15)	0.0187 (3)
H11A	−0.0617	0.1502	0.4526	0.022*
C12	0.21502 (17)	0.12527 (4)	0.58471 (14)	0.0162 (2)
C13	0.42785 (17)	0.13953 (4)	0.64815 (14)	0.0176 (3)
H13A	0.5238	0.1182	0.7028	0.021*
C14	0.49460 (17)	0.18430 (4)	0.63022 (14)	0.0175 (2)
H14A	0.6355	0.1926	0.6722	0.021*
C15	0.30017 (19)	0.04552 (4)	0.67163 (16)	0.0229 (3)
H15A	0.3783	0.0553	0.7812	0.034*
H15B	0.4027	0.0401	0.5793	0.034*
H15C	0.2218	0.0177	0.6943	0.034*
C16	−0.06638 (18)	0.06583 (4)	0.53393 (16)	0.0222 (3)
H16A	−0.1766	0.0881	0.5599	0.033*
H16B	−0.1035	0.0368	0.5860	0.033*
H16C	−0.0590	0.0626	0.4049	0.033*

	U11	U22	U33	U12	U13	U23
N1	0.0189 (5)	0.0166 (5)	0.0216 (5)	0.0000 (4)	0.0009 (4)	0.0003 (4)
N2	0.0295 (5)	0.0194 (5)	0.0304 (6)	−0.0017 (4)	0.0058 (4)	−0.0035 (4)
N3	0.0188 (5)	0.0154 (5)	0.0224 (5)	−0.0007 (4)	0.0011 (4)	0.0008 (4)
C1	0.0179 (5)	0.0166 (5)	0.0162 (5)	−0.0016 (4)	−0.0034 (4)	0.0017 (4)
C2	0.0150 (5)	0.0187 (6)	0.0170 (5)	−0.0024 (4)	0.0005 (4)	0.0002 (4)
C3	0.0190 (5)	0.0182 (6)	0.0151 (5)	−0.0014 (4)	−0.0010 (4)	−0.0016 (4)
C4	0.0211 (5)	0.0184 (6)	0.0172 (5)	−0.0060 (4)	−0.0022 (4)	0.0005 (4)
C5	0.0161 (5)	0.0262 (6)	0.0196 (6)	−0.0049 (5)	0.0002 (4)	0.0005 (5)
C6	0.0149 (5)	0.0231 (6)	0.0209 (5)	0.0023 (4)	−0.0010 (4)	−0.0014 (4)
C7	0.0225 (6)	0.0170 (6)	0.0199 (5)	−0.0056 (5)	0.0009 (4)	−0.0009 (4)
C8	0.0165 (5)	0.0171 (6)	0.0187 (5)	0.0033 (4)	0.0027 (4)	0.0015 (4)
C9	0.0171 (5)	0.0170 (5)	0.0174 (6)	0.0012 (4)	0.0039 (4)	0.0001 (4)
C10	0.0164 (5)	0.0180 (6)	0.0221 (6)	0.0042 (4)	0.0013 (4)	0.0018 (4)
C11	0.0147 (5)	0.0196 (6)	0.0219 (6)	−0.0004 (4)	0.0014 (4)	−0.0001 (4)
C12	0.0181 (5)	0.0162 (5)	0.0148 (5)	0.0015 (4)	0.0046 (4)	−0.0003 (4)
C13	0.0186 (5)	0.0176 (5)	0.0167 (5)	0.0041 (4)	0.0013 (4)	0.0013 (4)
C14	0.0162 (5)	0.0189 (5)	0.0175 (5)	0.0008 (4)	0.0012 (4)	−0.0007 (4)
C15	0.0292 (6)	0.0158 (6)	0.0233 (6)	0.0000 (5)	−0.0039 (5)	0.0009 (4)
C16	0.0198 (6)	0.0184 (6)	0.0285 (6)	−0.0020 (4)	0.0035 (5)	−0.0007 (5)

N1—C8	1.2833 (14)	C8—H8A	0.9300
N1—C1	1.4105 (14)	C9—C10	1.3998 (15)
N2—C7	1.1466 (15)	C9—C14	1.4013 (15)
N3—C12	1.3746 (14)	C10—C11	1.3834 (16)
N3—C15	1.4526 (14)	C10—H10A	0.9300
N3—C16	1.4531 (14)	C11—C12	1.4109 (15)
C1—C2	1.3924 (15)	C11—H11A	0.9300
C1—C6	1.3984 (15)	C12—C13	1.4181 (15)
C2—C3	1.3986 (15)	C13—C14	1.3743 (15)
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.3988 (15)	C14—H14A	0.9300
C3—C7	1.4434 (16)	C15—H15A	0.9600
C4—C5	1.3854 (16)	C15—H15B	0.9600
C4—H4A	0.9300	C15—H15C	0.9600
C5—C6	1.3836 (16)	C16—H16A	0.9600
C5—H5A	0.9300	C16—H16B	0.9600
C6—H6A	0.9300	C16—H16C	0.9600
C8—C9	1.4501 (15)
C8—N1—C1	117.49 (9)	C14—C9—C8	121.43 (10)
C12—N3—C15	120.76 (9)	C11—C10—C9	121.69 (10)
C12—N3—C16	120.20 (9)	C11—C10—H10A	119.2
C15—N3—C16	116.99 (9)	C9—C10—H10A	119.2
C2—C1—C6	119.09 (10)	C10—C11—C12	120.71 (10)
C2—C1—N1	122.86 (10)	C10—C11—H11A	119.6
C6—C1—N1	118.04 (10)	C12—C11—H11A	119.6
C1—C2—C3	119.44 (10)	N3—C12—C11	121.91 (9)
C1—C2—H2A	120.3	N3—C12—C13	120.73 (10)
C3—C2—H2A	120.3	C11—C12—C13	117.33 (10)
C2—C3—C4	121.21 (10)	C14—C13—C12	121.08 (10)
C2—C3—C7	119.83 (10)	C14—C13—H13A	119.5
C4—C3—C7	118.94 (10)	C12—C13—H13A	119.5
C5—C4—C3	118.64 (10)	C13—C14—C9	121.54 (10)
C5—C4—H4A	120.7	C13—C14—H14A	119.2
C3—C4—H4A	120.7	C9—C14—H14A	119.2
C6—C5—C4	120.59 (10)	N3—C15—H15A	109.5
C6—C5—H5A	119.7	N3—C15—H15B	109.5
C4—C5—H5A	119.7	H15A—C15—H15B	109.5
C5—C6—C1	120.95 (10)	N3—C15—H15C	109.5
C5—C6—H6A	119.5	H15A—C15—H15C	109.5
C1—C6—H6A	119.5	H15B—C15—H15C	109.5
N2—C7—C3	177.67 (13)	N3—C16—H16A	109.5
N1—C8—C9	123.00 (10)	N3—C16—H16B	109.5
N1—C8—H8A	118.5	H16A—C16—H16B	109.5
C9—C8—H8A	118.5	N3—C16—H16C	109.5
C10—C9—C14	117.61 (10)	H16A—C16—H16C	109.5
C10—C9—C8	120.95 (10)	H16B—C16—H16C	109.5