(2E,4E)-N-Benzyl-2-cyano-5-phenyl-penta-2,4-dienamide.

In the title compound, C(19)H(16)N(2)O, the mol-ecule adopts an E configuration about the two C=C double bonds. The dihedral angle between the phenyl rings is 88.89 (8)°. In the crystal, mol-ecules are linked by inter-molecular N-H⋯N and C-H⋯O hydrogen bonds into chains running parallel to [130].

Related literature

For the use of malononitrile-containing compounds as building blocks in organic synthesis, see: Liu et al. (2002 ▶); Sepiol & Milart (1985 ▶); Zhang et al. (2003 ▶). For a related structure, see: Kang & Chen (2009 ▶).

Experimental

Crystal data

C19H16N2O

M = 288.34

Monoclinic,

a = 19.5823 (19) Å

b = 5.6386 (8) Å

c = 28.450 (3) Å

β = 94.912 (9)°

V = 3129.8 (6) Å3

Z = 8

Cu Kα radiation

μ = 0.61 mm−1

T = 291 K

0.30 × 0.24 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.839, T max = 0.889

6165 measured reflections

2789 independent reflections

1843 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.137

S = 1.05

2789 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036397/rz2635sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036397/rz2635Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036397/rz2635Isup3.cml

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

C19H16N2O	F(000) = 1216
Mr = 288.34	Dx = 1.224 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 1369 reflections
a = 19.5823 (19) Å	θ = 3.1–69.3°
b = 5.6386 (8) Å	µ = 0.61 mm−1
c = 28.450 (3) Å	T = 291 K
β = 94.912 (9)°	Needle, yellow
V = 3129.8 (6) Å3	0.30 × 0.24 × 0.20 mm
Z = 8

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer	2789 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1843 reflections with I > 2σ(I)
mirror	Rint = 0.027
Detector resolution: 15.9149 pixels mm-1	θmax = 67.1°, θmin = 3.1°
ω scans	h = −23→21
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −4→6
Tmin = 0.839, Tmax = 0.889	l = −33→31
6165 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0532P)2 + 0.3114P] where P = (Fo2 + 2Fc2)/3
2789 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.13 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
O1	0.28610 (7)	1.1494 (3)	0.45363 (5)	0.0770 (5)
N2	0.36754 (9)	1.4308 (3)	0.45249 (6)	0.0650 (5)
H2	0.4081	1.4745	0.4629	0.078*
N1	0.50308 (9)	1.2707 (4)	0.53540 (7)	0.0751 (6)
C10	0.38243 (9)	1.1118 (4)	0.50910 (7)	0.0559 (5)
C5	0.38487 (10)	0.4455 (4)	0.62469 (7)	0.0596 (5)
C14	0.33781 (10)	1.5116 (4)	0.36648 (7)	0.0592 (5)
C11	0.44961 (10)	1.1992 (4)	0.52414 (7)	0.0594 (5)
C8	0.38929 (10)	0.7868 (4)	0.56840 (7)	0.0627 (6)
H8	0.4334	0.8274	0.5805	0.075*
C9	0.35694 (10)	0.9231 (4)	0.53033 (7)	0.0592 (5)
H9	0.3131	0.8752	0.5190	0.071*
C12	0.34132 (9)	1.2332 (4)	0.46947 (7)	0.0578 (5)
C7	0.35797 (10)	0.6024 (4)	0.58708 (7)	0.0609 (5)
H7	0.3135	0.5711	0.5744	0.073*
C19	0.31165 (11)	1.6639 (5)	0.33143 (9)	0.0766 (7)
H19	0.2898	1.8023	0.3397	0.092*
C13	0.32942 (12)	1.5726 (4)	0.41717 (8)	0.0706 (6)
H13B	0.3426	1.7370	0.4222	0.085*
H13A	0.2812	1.5603	0.4221	0.085*
C4	0.45148 (11)	0.4587 (5)	0.64515 (9)	0.0799 (7)
H4	0.4805	0.5765	0.6355	0.096*
C15	0.36965 (11)	1.3083 (4)	0.35289 (8)	0.0718 (6)
H15	0.3875	1.2015	0.3756	0.086*
C6	0.34295 (11)	0.2684 (4)	0.64009 (8)	0.0679 (6)
H6	0.2978	0.2571	0.6271	0.081*
C1	0.36710 (12)	0.1092 (5)	0.67424 (8)	0.0792 (7)
H1	0.3383	−0.0082	0.6842	0.095*
C2	0.43355 (13)	0.1235 (5)	0.69361 (9)	0.0847 (7)
H2A	0.4501	0.0138	0.7162	0.102*
C18	0.31711 (13)	1.6154 (6)	0.28437 (9)	0.0899 (8)
H18	0.2986	1.7197	0.2614	0.108*
C16	0.37529 (14)	1.2612 (5)	0.30529 (10)	0.0889 (8)
H16	0.3968	1.1232	0.2965	0.107*
C3	0.47553 (12)	0.3004 (6)	0.67950 (10)	0.0923 (9)
H3	0.5202	0.3133	0.6932	0.111*
C17	0.34949 (15)	1.4158 (6)	0.27158 (10)	0.0915 (8)
H17	0.3540	1.3848	0.2399	0.110*

	U11	U22	U33	U12	U13	U23
O1	0.0564 (8)	0.0861 (12)	0.0854 (11)	−0.0154 (8)	−0.0120 (7)	−0.0014 (9)
N2	0.0644 (10)	0.0644 (12)	0.0641 (11)	−0.0098 (9)	−0.0066 (8)	−0.0037 (9)
N1	0.0593 (11)	0.0816 (14)	0.0830 (13)	−0.0103 (10)	−0.0031 (9)	−0.0061 (11)
C10	0.0512 (10)	0.0589 (13)	0.0574 (11)	−0.0039 (9)	0.0046 (9)	−0.0090 (10)
C5	0.0566 (11)	0.0641 (13)	0.0577 (12)	−0.0048 (10)	0.0033 (9)	−0.0068 (11)
C14	0.0547 (11)	0.0582 (13)	0.0638 (13)	−0.0093 (10)	0.0003 (9)	−0.0040 (11)
C11	0.0554 (11)	0.0611 (13)	0.0614 (12)	−0.0032 (10)	0.0023 (9)	−0.0057 (11)
C8	0.0519 (11)	0.0733 (15)	0.0623 (13)	−0.0059 (10)	0.0023 (9)	−0.0048 (11)
C9	0.0495 (10)	0.0668 (14)	0.0608 (12)	−0.0053 (10)	0.0029 (9)	−0.0101 (11)
C12	0.0519 (11)	0.0636 (13)	0.0573 (12)	−0.0025 (10)	0.0019 (9)	−0.0085 (11)
C7	0.0511 (11)	0.0680 (14)	0.0629 (12)	−0.0034 (10)	0.0001 (9)	−0.0076 (11)
C19	0.0719 (14)	0.0764 (16)	0.0806 (16)	0.0030 (12)	0.0017 (12)	0.0066 (14)
C13	0.0757 (14)	0.0616 (14)	0.0729 (15)	0.0023 (11)	−0.0032 (11)	−0.0045 (12)
C4	0.0620 (13)	0.0937 (19)	0.0823 (16)	−0.0152 (13)	−0.0035 (12)	0.0148 (15)
C15	0.0827 (15)	0.0593 (14)	0.0733 (15)	−0.0022 (12)	0.0069 (12)	−0.0006 (12)
C6	0.0634 (12)	0.0743 (15)	0.0650 (14)	−0.0088 (11)	−0.0009 (10)	−0.0010 (12)
C1	0.0856 (16)	0.0811 (17)	0.0708 (15)	−0.0211 (13)	0.0057 (12)	0.0018 (14)
C2	0.0906 (17)	0.0924 (19)	0.0690 (15)	−0.0053 (15)	−0.0060 (13)	0.0134 (15)
C18	0.0853 (17)	0.109 (2)	0.0735 (17)	−0.0067 (16)	−0.0059 (13)	0.0159 (17)
C16	0.110 (2)	0.0765 (18)	0.0836 (19)	−0.0086 (15)	0.0259 (15)	−0.0155 (16)
C3	0.0691 (14)	0.114 (2)	0.0909 (19)	−0.0113 (15)	−0.0134 (13)	0.0168 (18)
C17	0.105 (2)	0.101 (2)	0.0694 (16)	−0.0202 (18)	0.0087 (15)	−0.0075 (17)

O1—C12	1.230 (2)	C19—H19	0.9300
N2—C12	1.334 (3)	C13—H13B	0.9700
N2—C13	1.442 (3)	C13—H13A	0.9700
N2—H2	0.8600	C4—C3	1.377 (3)
N1—C11	1.142 (2)	C4—H4	0.9300
C10—C9	1.341 (3)	C15—C16	1.394 (3)
C10—C11	1.435 (3)	C15—H15	0.9300
C10—C12	1.494 (3)	C6—C1	1.377 (3)
C5—C4	1.384 (3)	C6—H6	0.9300
C5—C6	1.387 (3)	C1—C2	1.371 (3)
C5—C7	1.452 (3)	C1—H1	0.9300
C14—C15	1.376 (3)	C2—C3	1.374 (4)
C14—C19	1.381 (3)	C2—H2A	0.9300
C14—C13	1.505 (3)	C18—C17	1.356 (4)
C8—C7	1.340 (3)	C18—H18	0.9300
C8—C9	1.431 (3)	C16—C17	1.361 (4)
C8—H8	0.9300	C16—H16	0.9300
C9—H9	0.9300	C3—H3	0.9300
C7—H7	0.9300	C17—H17	0.9300
C19—C18	1.380 (3)
C12—N2—C13	121.55 (18)	N2—C13—H13A	108.1
C12—N2—H2	119.2	C14—C13—H13A	108.1
C13—N2—H2	119.2	H13B—C13—H13A	107.3
C9—C10—C11	120.34 (19)	C3—C4—C5	121.1 (2)
C9—C10—C12	120.41 (18)	C3—C4—H4	119.4
C11—C10—C12	119.25 (19)	C5—C4—H4	119.4
C4—C5—C6	117.9 (2)	C14—C15—C16	120.5 (2)
C4—C5—C7	123.1 (2)	C14—C15—H15	119.8
C6—C5—C7	118.96 (19)	C16—C15—H15	119.8
C15—C14—C19	117.7 (2)	C1—C6—C5	121.0 (2)
C15—C14—C13	123.3 (2)	C1—C6—H6	119.5
C19—C14—C13	119.0 (2)	C5—C6—H6	119.5
N1—C11—C10	178.8 (2)	C2—C1—C6	120.1 (2)
C7—C8—C9	121.93 (19)	C2—C1—H1	119.9
C7—C8—H8	119.0	C6—C1—H1	119.9
C9—C8—H8	119.0	C1—C2—C3	119.7 (2)
C10—C9—C8	127.54 (19)	C1—C2—H2A	120.1
C10—C9—H9	116.2	C3—C2—H2A	120.1
C8—C9—H9	116.2	C17—C18—C19	120.1 (3)
O1—C12—N2	122.8 (2)	C17—C18—H18	120.0
O1—C12—C10	120.0 (2)	C19—C18—H18	120.0
N2—C12—C10	117.16 (17)	C17—C16—C15	120.5 (3)
C8—C7—C5	127.99 (19)	C17—C16—H16	119.8
C8—C7—H7	116.0	C15—C16—H16	119.8
C5—C7—H7	116.0	C2—C3—C4	120.1 (2)
C18—C19—C14	121.5 (2)	C2—C3—H3	120.0
C18—C19—H19	119.2	C4—C3—H3	120.0
C14—C19—H19	119.2	C18—C17—C16	119.8 (3)
N2—C13—C14	116.66 (19)	C18—C17—H17	120.1
N2—C13—H13B	108.1	C16—C17—H17	120.1
C14—C13—H13B	108.1
C11—C10—C9—C8	0.0 (3)	C19—C14—C13—N2	−169.62 (19)
C12—C10—C9—C8	179.81 (19)	C6—C5—C4—C3	0.4 (4)
C7—C8—C9—C10	179.2 (2)	C7—C5—C4—C3	−177.5 (3)
C13—N2—C12—O1	6.1 (3)	C19—C14—C15—C16	0.5 (3)
C13—N2—C12—C10	−174.48 (19)	C13—C14—C15—C16	179.5 (2)
C9—C10—C12—O1	−5.8 (3)	C4—C5—C6—C1	−0.8 (3)
C11—C10—C12—O1	174.09 (19)	C7—C5—C6—C1	177.2 (2)
C9—C10—C12—N2	174.82 (19)	C5—C6—C1—C2	−0.1 (4)
C11—C10—C12—N2	−5.3 (3)	C6—C1—C2—C3	1.4 (4)
C9—C8—C7—C5	178.3 (2)	C14—C19—C18—C17	−0.8 (4)
C4—C5—C7—C8	−4.3 (4)	C14—C15—C16—C17	0.1 (4)
C6—C5—C7—C8	177.9 (2)	C1—C2—C3—C4	−1.8 (4)
C15—C14—C19—C18	−0.1 (3)	C5—C4—C3—C2	0.9 (4)
C13—C14—C19—C18	−179.2 (2)	C19—C18—C17—C16	1.4 (4)
C12—N2—C13—C14	−89.9 (3)	C15—C16—C17—C18	−1.0 (4)
C15—C14—C13—N2	11.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1i	0.86	2.25	3.037 (2)	152.
C7—H7···O1ii	0.93	2.39	3.280 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1i	0.86	2.25	3.037 (2)	152
C7—H7⋯O1ii	0.93	2.39	3.280 (2)	160

Symmetry codes: (i) ; (ii) .