(E)-2-Cyano-3-[4-(dimethyl-amino)phen-yl]-N-phenyl-prop-2-enamide.

In the title compound, C(18)H(17)N(3)O, the dihedral angle between the phenyl and benzene rings is 11.22 (14)°. Apart from the methyl H atoms, the mol-ecule is close to planar, with a maximum deviation of 0.145 (3) Å. Intra-molecular C-H⋯O and C-H⋯N inter-actions occur. In the crystal, inversion dimers linked by pairs of N-H⋯N hydrogen bonds occur, resulting in an R(2) (2)(12) ring motif. Further C-H⋯N and C-H⋯O bonds generate R(1) (2)(7) and R(2) (2)(22) motifs and a C-H⋯π inter-action also occurs.

Related literature

For background on the properties and uses of organic dyes, see: Grabowski et al. (2003 ▶); Guo et al. (2007 ▶); Kwak et al. (2008 ▶); Moylan et al. (1996 ▶). For reference structural data, see Allen et al. (1987 ▶). For graph-set terminology, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H17N3O

M = 291.35

Monoclinic,

a = 12.0639 (19) Å

b = 19.983 (3) Å

c = 6.3960 (9) Å

β = 94.870 (6)°

V = 1536.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.44 × 0.09 × 0.07 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: none

15701 measured reflections

3484 independent reflections

1380 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.165

S = 0.97

3484 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017681/hb2974sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017681/hb2974Isup2.hkl

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

C18H17N3O	F(000) = 616
Mr = 291.35	Dx = 1.260 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1223 reflections
a = 12.0639 (19) Å	θ = 3.4–19.8°
b = 19.983 (3) Å	µ = 0.08 mm−1
c = 6.3960 (9) Å	T = 296 K
β = 94.870 (6)°	Prism, red
V = 1536.3 (4) Å3	0.44 × 0.09 × 0.07 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	1380 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.082
graphite	θmax = 27.5°, θmin = 2.0°
φ and ω scans	h = −15→15
15701 measured reflections	k = −25→25
3484 independent reflections	l = −8→5

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)] = 0.060	H-atom parameters constrained
wR(F2) = 0.165	w = 1/[σ2(Fo2) + (0.0643P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
3484 reflections	Δρmax = 0.19 e Å−3
202 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: 0.0038 (12)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.37797 (16)	0.07494 (10)	0.5929 (3)	0.0639 (8)
N1	0.19658 (18)	0.07922 (10)	0.6643 (3)	0.0444 (8)
N2	0.0364 (2)	−0.00214 (14)	0.2850 (4)	0.0714 (10)
N3	0.3109 (2)	−0.16820 (12)	−0.4827 (4)	0.0619 (10)
C1	0.1026 (3)	0.13303 (16)	0.9294 (5)	0.0740 (12)
C2	0.0994 (3)	0.17166 (17)	1.1086 (6)	0.0876 (17)
C3	0.1948 (4)	0.19793 (16)	1.2024 (5)	0.0757 (16)
C4	0.2923 (3)	0.18648 (16)	1.1198 (5)	0.0754 (14)
C5	0.2976 (3)	0.14743 (15)	0.9411 (5)	0.0615 (11)
C6	0.2018 (2)	0.12058 (13)	0.8457 (4)	0.0439 (10)
C7	0.2811 (2)	0.05968 (13)	0.5505 (4)	0.0425 (10)
C8	0.2467 (2)	0.01696 (13)	0.3648 (4)	0.0391 (9)
C9	0.1308 (3)	0.00579 (14)	0.3162 (4)	0.0480 (10)
C10	0.3244 (2)	−0.00906 (13)	0.2492 (4)	0.0414 (9)
C11	0.3150 (2)	−0.04902 (13)	0.0609 (4)	0.0392 (9)
C12	0.2159 (2)	−0.06559 (14)	−0.0565 (4)	0.0480 (10)
C13	0.2145 (2)	−0.10416 (14)	−0.2344 (4)	0.0488 (10)
C14	0.3122 (2)	−0.12898 (14)	−0.3082 (4)	0.0458 (10)
C15	0.4128 (2)	−0.11114 (14)	−0.1943 (4)	0.0506 (11)
C16	0.4124 (2)	−0.07274 (13)	−0.0153 (4)	0.0471 (10)
C17	0.2077 (3)	−0.18754 (16)	−0.5982 (5)	0.0770 (16)
C18	0.4122 (3)	−0.19039 (16)	−0.5680 (5)	0.0755 (15)
H1	0.03700	0.11530	0.86510	0.0890*
H1A	0.13160	0.06470	0.62090	0.0530*
H2	0.03200	0.17960	1.16470	0.1050*
H3	0.19290	0.22370	1.32310	0.0910*
H4	0.35720	0.20510	1.18370	0.0900*
H5	0.36550	0.13960	0.88690	0.0740*
H10	0.39720	0.00050	0.30000	0.0500*
H12	0.14890	−0.05000	−0.01300	0.0580*
H13	0.14660	−0.11400	−0.30780	0.0590*
H15	0.48010	−0.12540	−0.24010	0.0610*
H16	0.48010	−0.06220	0.05780	0.0570*
H17A	0.15590	−0.20220	−0.50190	0.1150*
H17B	0.22150	−0.22340	−0.69260	0.1150*
H17C	0.17720	−0.14990	−0.67680	0.1150*
H18A	0.46280	−0.15340	−0.57210	0.1130*
H18B	0.39490	−0.20720	−0.70750	0.1130*
H18C	0.44600	−0.22520	−0.48100	0.1130*

	U11	U22	U33	U12	U13	U23
O1	0.0432 (13)	0.0847 (17)	0.0632 (13)	−0.0141 (12)	0.0010 (10)	−0.0260 (12)
N1	0.0437 (14)	0.0484 (15)	0.0409 (12)	−0.0052 (12)	0.0033 (11)	−0.0120 (11)
N2	0.0486 (17)	0.106 (2)	0.0607 (16)	−0.0128 (16)	0.0113 (13)	−0.0316 (15)
N3	0.0715 (19)	0.0641 (18)	0.0502 (14)	−0.0024 (15)	0.0063 (14)	−0.0211 (13)
C1	0.075 (2)	0.073 (2)	0.079 (2)	−0.031 (2)	0.035 (2)	−0.031 (2)
C2	0.108 (3)	0.075 (3)	0.088 (3)	−0.035 (2)	0.056 (2)	−0.036 (2)
C3	0.129 (4)	0.050 (2)	0.0486 (19)	−0.003 (2)	0.010 (2)	−0.0106 (16)
C4	0.087 (3)	0.068 (2)	0.066 (2)	0.019 (2)	−0.024 (2)	−0.0251 (19)
C5	0.061 (2)	0.059 (2)	0.0608 (19)	0.0158 (17)	−0.0159 (16)	−0.0210 (17)
C6	0.060 (2)	0.0341 (16)	0.0377 (14)	0.0019 (15)	0.0046 (15)	0.0007 (13)
C7	0.0429 (18)	0.0431 (18)	0.0412 (15)	−0.0066 (15)	0.0020 (14)	−0.0047 (13)
C8	0.0359 (16)	0.0451 (18)	0.0361 (13)	−0.0036 (13)	0.0013 (12)	0.0012 (12)
C9	0.0472 (19)	0.058 (2)	0.0396 (15)	−0.0055 (16)	0.0085 (14)	−0.0122 (14)
C10	0.0401 (16)	0.0427 (17)	0.0408 (14)	−0.0019 (14)	−0.0004 (13)	0.0003 (13)
C11	0.0377 (17)	0.0409 (17)	0.0387 (14)	−0.0017 (13)	0.0018 (13)	−0.0005 (13)
C12	0.0423 (18)	0.060 (2)	0.0425 (15)	0.0023 (15)	0.0080 (13)	−0.0058 (14)
C13	0.0477 (19)	0.058 (2)	0.0399 (15)	−0.0051 (15)	−0.0006 (13)	−0.0048 (14)
C14	0.058 (2)	0.0411 (18)	0.0389 (15)	−0.0003 (15)	0.0071 (15)	−0.0008 (13)
C15	0.051 (2)	0.049 (2)	0.0526 (17)	0.0034 (15)	0.0100 (15)	−0.0066 (15)
C16	0.0447 (18)	0.0462 (19)	0.0503 (16)	0.0012 (15)	0.0037 (14)	−0.0038 (14)
C17	0.093 (3)	0.079 (3)	0.057 (2)	−0.007 (2)	−0.0048 (19)	−0.0198 (18)
C18	0.098 (3)	0.073 (3)	0.0592 (19)	0.001 (2)	0.0285 (19)	−0.0163 (17)

O1—C7	1.216 (3)	C12—C13	1.373 (4)
N1—C6	1.422 (3)	C13—C14	1.397 (4)
N1—C7	1.359 (3)	C14—C15	1.407 (4)
N2—C9	1.150 (4)	C15—C16	1.379 (4)
N3—C14	1.363 (4)	C1—H1	0.9300
N3—C17	1.445 (4)	C2—H2	0.9300
N3—C18	1.450 (4)	C3—H3	0.9300
N1—H1A	0.8600	C4—H4	0.9300
C1—C2	1.385 (5)	C5—H5	0.9300
C1—C6	1.375 (4)	C10—H10	0.9300
C2—C3	1.358 (6)	C12—H12	0.9300
C3—C4	1.349 (6)	C13—H13	0.9300
C4—C5	1.390 (4)	C15—H15	0.9300
C5—C6	1.370 (4)	C16—H16	0.9300
C7—C8	1.493 (4)	C17—H17A	0.9600
C8—C9	1.424 (4)	C17—H17B	0.9600
C8—C10	1.347 (4)	C17—H17C	0.9600
C10—C11	1.442 (4)	C18—H18A	0.9600
C11—C16	1.393 (3)	C18—H18B	0.9600
C11—C12	1.397 (4)	C18—H18C	0.9600
C6—N1—C7	128.4 (2)	C2—C1—H1	120.00
C14—N3—C17	121.5 (2)	C6—C1—H1	120.00
C14—N3—C18	122.2 (2)	C1—C2—H2	120.00
C17—N3—C18	116.3 (3)	C3—C2—H2	120.00
C6—N1—H1A	116.00	C2—C3—H3	120.00
C7—N1—H1A	116.00	C4—C3—H3	120.00
C2—C1—C6	120.6 (3)	C3—C4—H4	119.00
C1—C2—C3	119.9 (3)	C5—C4—H4	119.00
C2—C3—C4	119.7 (3)	C4—C5—H5	120.00
C3—C4—C5	121.3 (3)	C6—C5—H5	120.00
C4—C5—C6	119.4 (3)	C8—C10—H10	114.00
N1—C6—C5	124.7 (2)	C11—C10—H10	114.00
C1—C6—C5	119.0 (3)	C11—C12—H12	119.00
N1—C6—C1	116.3 (2)	C13—C12—H12	119.00
N1—C7—C8	114.8 (2)	C12—C13—H13	119.00
O1—C7—N1	124.0 (2)	C14—C13—H13	119.00
O1—C7—C8	121.2 (2)	C14—C15—H15	120.00
C9—C8—C10	122.4 (2)	C16—C15—H15	120.00
C7—C8—C10	119.9 (2)	C11—C16—H16	119.00
C7—C8—C9	117.7 (2)	C15—C16—H16	119.00
N2—C9—C8	177.1 (3)	N3—C17—H17A	109.00
C8—C10—C11	131.6 (2)	N3—C17—H17B	109.00
C12—C11—C16	116.1 (2)	N3—C17—H17C	109.00
C10—C11—C12	125.7 (2)	H17A—C17—H17B	109.00
C10—C11—C16	118.2 (2)	H17A—C17—H17C	109.00
C11—C12—C13	121.9 (2)	H17B—C17—H17C	110.00
C12—C13—C14	121.9 (2)	N3—C18—H18A	109.00
N3—C14—C15	121.3 (2)	N3—C18—H18B	109.00
N3—C14—C13	122.0 (2)	N3—C18—H18C	109.00
C13—C14—C15	116.8 (2)	H18A—C18—H18B	109.00
C14—C15—C16	120.5 (2)	H18A—C18—H18C	110.00
C11—C16—C15	122.9 (2)	H18B—C18—H18C	109.00
C6—N1—C7—O1	1.3 (4)	O1—C7—C8—C9	−175.1 (2)
C7—N1—C6—C1	179.4 (3)	O1—C7—C8—C10	4.5 (4)
C7—N1—C6—C5	−1.4 (4)	N1—C7—C8—C9	5.0 (3)
C6—N1—C7—C8	−178.8 (2)	C9—C8—C10—C11	2.3 (5)
C18—N3—C14—C15	−3.8 (4)	C7—C8—C10—C11	−177.2 (3)
C17—N3—C14—C13	−1.5 (4)	C8—C10—C11—C12	5.6 (5)
C18—N3—C14—C13	175.8 (3)	C8—C10—C11—C16	−175.5 (3)
C17—N3—C14—C15	179.0 (3)	C10—C11—C12—C13	−179.9 (3)
C2—C1—C6—N1	178.7 (3)	C16—C11—C12—C13	1.3 (4)
C2—C1—C6—C5	−0.6 (5)	C10—C11—C16—C15	−179.8 (2)
C6—C1—C2—C3	0.4 (5)	C12—C11—C16—C15	−0.8 (4)
C1—C2—C3—C4	0.3 (5)	C11—C12—C13—C14	−0.1 (4)
C2—C3—C4—C5	−0.8 (5)	C12—C13—C14—N3	178.9 (3)
C3—C4—C5—C6	0.7 (5)	C12—C13—C14—C15	−1.6 (4)
C4—C5—C6—N1	−179.1 (3)	N3—C14—C15—C16	−178.5 (3)
C4—C5—C6—C1	0.0 (4)	C13—C14—C15—C16	2.0 (4)
N1—C7—C8—C10	−175.5 (2)	C14—C15—C16—C11	−0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1	0.93	2.30	2.892 (4)	121
C12—H12···N2	0.93	2.61	3.445 (4)	149
N1—H1A···N2i	0.86	2.50	3.245 (3)	146
C1—H1···N2i	0.93	2.58	3.338 (4)	139
C18—H18A···O1ii	0.96	2.49	3.439 (4)	169
C3—H3···Cg1iii	0.93	2.66	3.514 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1	0.93	2.30	2.892 (4)	121
C12—H12⋯N2	0.93	2.61	3.445 (4)	149
N1—H1A⋯N2i	0.86	2.50	3.245 (3)	146
C1—H1⋯N2i	0.93	2.58	3.338 (4)	139
C18—H18A⋯O1ii	0.96	2.49	3.439 (4)	169
C3—H3⋯Cg1iii	0.93	2.66	3.514 (3)	152

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C1–C6 phenyl ring.