(E)-N-Benzyl-2-cyano-3-phenyl-acryl-amide.

In the title compound, C(17)H(14)N(2)O, the N-benzyl-formamide and phenyl groups are located on the opposite sides of the C=C bond, showing an E configuration; the terminal phenyl rings are twisted to each other at a dihedral angle of 63.61 (7)°. Inter-molecular classical N-H⋯N and weak C-H⋯O hydrogen bonds occur in the crystal structure.

Related literature

For the use of malononitrile-containing compounds as building blocks in syntheses, see: Lee et al. (2002 ▶); Rajan et al. (2001 ▶); Yingyongnarongkul et al. (2006 ▶). For a related structure, see: Kang & Chen (2009 ▶).

Experimental

Crystal data

C17H14N2O

M = 262.30

Triclinic,

a = 5.8956 (3) Å

b = 9.9224 (5) Å

c = 12.1400 (7) Å

α = 94.508 (5)°

β = 99.544 (4)°

γ = 98.895 (4)°

V = 687.95 (6) Å3

Z = 2

Cu Kα radiation

μ = 0.64 mm−1

T = 291 K

0.36 × 0.35 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.803, T max = 0.832

5416 measured reflections

2407 independent reflections

2202 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.05

2407 reflections

185 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.12 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; 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 datablocks global, I. DOI: 10.1107/S1600536810049548/xu5098sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049548/xu5098Isup2.hkl

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

C17H14N2O	Z = 2
Mr = 262.30	F(000) = 276
Triclinic, P1	Dx = 1.266 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 5.8956 (3) Å	Cell parameters from 3956 reflections
b = 9.9224 (5) Å	θ = 4.5–72.2°
c = 12.1400 (7) Å	µ = 0.64 mm−1
α = 94.508 (5)°	T = 291 K
β = 99.544 (4)°	Block, yellow
γ = 98.895 (4)°	0.36 × 0.35 × 0.30 mm
V = 687.95 (6) Å3

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer	2407 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2202 reflections with I > 2σ(I)
mirror	Rint = 0.018
Detector resolution: 7.9575 pixels mm-1	θmax = 67.1°, θmin = 4.5°
ω scans	h = −6→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −11→11
Tmin = 0.803, Tmax = 0.832	l = −14→14
5416 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0452P)2 + 0.101P] where P = (Fo2 + 2Fc2)/3
2407 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.14 e Å−3
2 restraints	Δρmin = −0.12 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	0.28178 (15)	0.43568 (9)	0.56771 (8)	0.0523 (3)
N2	0.53117 (17)	0.28418 (10)	0.58336 (8)	0.0424 (3)
C4	−0.2206 (2)	0.19407 (12)	0.31358 (9)	0.0398 (3)
C12	0.7670 (2)	0.35036 (12)	0.77490 (10)	0.0413 (3)
N1	0.2529 (2)	−0.02233 (11)	0.42829 (10)	0.0556 (3)
C8	0.1591 (2)	0.22182 (11)	0.45635 (9)	0.0371 (3)
C3	−0.3994 (2)	0.26728 (13)	0.27993 (11)	0.0471 (3)
H3	−0.3904	0.3563	0.3128	0.056*
C9	0.20860 (19)	0.08566 (12)	0.43834 (10)	0.0405 (3)
C7	−0.0298 (2)	0.26411 (11)	0.40119 (10)	0.0389 (3)
H7	−0.0409	0.3545	0.4229	0.047*
C11	0.7242 (2)	0.37901 (13)	0.65408 (11)	0.0458 (3)
H11A	0.6918	0.4717	0.6509	0.055*
H11B	0.8653	0.3745	0.6237	0.055*
C10	0.32978 (19)	0.32315 (11)	0.54175 (9)	0.0375 (3)
C2	−0.5896 (2)	0.20970 (15)	0.19856 (12)	0.0570 (4)
H2	−0.7080	0.2596	0.1776	0.068*
C17	0.9529 (2)	0.28819 (16)	0.81647 (12)	0.0576 (4)
H17	1.0518	0.2634	0.7691	0.069*
C15	0.8499 (3)	0.29793 (18)	0.99859 (13)	0.0689 (4)
H15	0.8778	0.2804	1.0733	0.083*
C13	0.6229 (2)	0.38575 (14)	0.84780 (12)	0.0536 (3)
H13	0.4967	0.4276	0.8216	0.064*
C5	−0.2386 (3)	0.06160 (14)	0.26135 (12)	0.0579 (4)
H5	−0.1209	0.0109	0.2813	0.069*
C6	−0.4295 (3)	0.00533 (15)	0.18032 (13)	0.0666 (4)
H6	−0.4404	−0.0835	0.1467	0.080*
C14	0.6643 (3)	0.35969 (16)	0.95881 (13)	0.0646 (4)
H14	0.5661	0.3840	1.0067	0.078*
C1	−0.6041 (3)	0.07908 (15)	0.14864 (12)	0.0613 (4)
H1	−0.7318	0.0405	0.0935	0.074*
C16	0.9936 (3)	0.26243 (19)	0.92760 (14)	0.0727 (5)
H16	1.1195	0.2206	0.9543	0.087*
H4	0.556 (2)	0.2006 (13)	0.5647 (12)	0.054 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0492 (5)	0.0412 (5)	0.0618 (6)	0.0158 (4)	−0.0034 (4)	−0.0101 (4)
N2	0.0437 (6)	0.0402 (5)	0.0415 (6)	0.0134 (4)	−0.0015 (4)	−0.0002 (4)
C4	0.0431 (6)	0.0387 (6)	0.0364 (6)	0.0082 (5)	0.0028 (5)	0.0033 (5)
C12	0.0383 (6)	0.0394 (6)	0.0423 (6)	0.0043 (5)	0.0002 (5)	0.0003 (5)
N1	0.0566 (7)	0.0418 (6)	0.0664 (7)	0.0175 (5)	−0.0001 (5)	0.0008 (5)
C8	0.0409 (6)	0.0347 (5)	0.0360 (6)	0.0089 (4)	0.0059 (5)	0.0023 (4)
C3	0.0502 (7)	0.0461 (7)	0.0434 (7)	0.0138 (5)	0.0008 (5)	0.0012 (5)
C9	0.0406 (6)	0.0386 (6)	0.0406 (6)	0.0097 (5)	0.0006 (5)	0.0016 (5)
C7	0.0436 (6)	0.0345 (6)	0.0388 (6)	0.0098 (5)	0.0061 (5)	0.0016 (5)
C11	0.0398 (6)	0.0491 (7)	0.0459 (7)	0.0060 (5)	0.0021 (5)	0.0051 (5)
C10	0.0405 (6)	0.0370 (6)	0.0355 (6)	0.0100 (5)	0.0059 (5)	0.0033 (4)
C2	0.0504 (8)	0.0660 (9)	0.0508 (8)	0.0160 (6)	−0.0066 (6)	0.0042 (6)
C17	0.0460 (7)	0.0747 (9)	0.0524 (8)	0.0190 (6)	0.0018 (6)	0.0059 (7)
C15	0.0760 (10)	0.0812 (11)	0.0422 (8)	0.0034 (8)	−0.0028 (7)	0.0101 (7)
C13	0.0560 (8)	0.0536 (8)	0.0543 (8)	0.0179 (6)	0.0109 (6)	0.0049 (6)
C5	0.0632 (8)	0.0441 (7)	0.0597 (8)	0.0163 (6)	−0.0101 (7)	−0.0042 (6)
C6	0.0784 (10)	0.0460 (8)	0.0625 (9)	0.0067 (7)	−0.0133 (8)	−0.0094 (7)
C14	0.0777 (10)	0.0672 (9)	0.0505 (8)	0.0113 (8)	0.0197 (7)	0.0003 (7)
C1	0.0586 (8)	0.0619 (9)	0.0514 (8)	−0.0007 (7)	−0.0119 (6)	0.0010 (7)
C16	0.0598 (9)	0.0964 (13)	0.0599 (9)	0.0238 (8)	−0.0093 (7)	0.0186 (9)

O1—C10	1.2240 (13)	C11—H11B	0.9700
N2—C10	1.3372 (14)	C2—C1	1.371 (2)
N2—C11	1.4612 (15)	C2—H2	0.9300
N2—H4	0.884 (12)	C17—C16	1.382 (2)
C4—C5	1.3945 (17)	C17—H17	0.9300
C4—C3	1.3954 (16)	C15—C16	1.368 (2)
C4—C7	1.4574 (16)	C15—C14	1.373 (2)
C12—C17	1.3824 (17)	C15—H15	0.9300
C12—C13	1.3862 (18)	C13—C14	1.381 (2)
C12—C11	1.5036 (17)	C13—H13	0.9300
N1—C9	1.1435 (15)	C5—C6	1.3781 (19)
C8—C7	1.3443 (16)	C5—H5	0.9300
C8—C9	1.4334 (15)	C6—C1	1.374 (2)
C8—C10	1.5084 (16)	C6—H6	0.9300
C3—C2	1.3803 (18)	C14—H14	0.9300
C3—H3	0.9300	C1—H1	0.9300
C7—H7	0.9300	C16—H16	0.9300
C11—H11A	0.9700
C10—N2—C11	122.18 (10)	C1—C2—C3	120.08 (13)
C10—N2—H4	120.6 (9)	C1—C2—H2	120.0
C11—N2—H4	117.1 (9)	C3—C2—H2	120.0
C5—C4—C3	117.89 (11)	C16—C17—C12	120.79 (14)
C5—C4—C7	125.69 (11)	C16—C17—H17	119.6
C3—C4—C7	116.41 (10)	C12—C17—H17	119.6
C17—C12—C13	118.10 (12)	C16—C15—C14	119.57 (14)
C17—C12—C11	120.65 (12)	C16—C15—H15	120.2
C13—C12—C11	121.25 (11)	C14—C15—H15	120.2
C7—C8—C9	123.69 (10)	C14—C13—C12	120.87 (13)
C7—C8—C10	118.37 (10)	C14—C13—H13	119.6
C9—C8—C10	117.94 (9)	C12—C13—H13	119.6
C2—C3—C4	121.03 (12)	C6—C5—C4	120.46 (12)
C2—C3—H3	119.5	C6—C5—H5	119.8
C4—C3—H3	119.5	C4—C5—H5	119.8
N1—C9—C8	177.26 (13)	C1—C6—C5	120.71 (13)
C8—C7—C4	131.72 (10)	C1—C6—H6	119.6
C8—C7—H7	114.1	C5—C6—H6	119.6
C4—C7—H7	114.1	C15—C14—C13	120.19 (14)
N2—C11—C12	113.92 (10)	C15—C14—H14	119.9
N2—C11—H11A	108.8	C13—C14—H14	119.9
C12—C11—H11A	108.8	C2—C1—C6	119.82 (13)
N2—C11—H11B	108.8	C2—C1—H1	120.1
C12—C11—H11B	108.8	C6—C1—H1	120.1
H11A—C11—H11B	107.7	C15—C16—C17	120.48 (14)
O1—C10—N2	123.51 (11)	C15—C16—H16	119.8
O1—C10—C8	119.71 (10)	C17—C16—H16	119.8
N2—C10—C8	116.76 (10)
C5—C4—C3—C2	0.8 (2)	C9—C8—C10—N2	8.94 (16)
C7—C4—C3—C2	−179.17 (12)	C4—C3—C2—C1	−0.6 (2)
C7—C8—C9—N1	−153 (3)	C13—C12—C17—C16	−0.1 (2)
C10—C8—C9—N1	27 (3)	C11—C12—C17—C16	179.64 (13)
C9—C8—C7—C4	−1.4 (2)	C17—C12—C13—C14	0.1 (2)
C10—C8—C7—C4	178.30 (11)	C11—C12—C13—C14	−179.67 (12)
C5—C4—C7—C8	−4.2 (2)	C3—C4—C5—C6	−0.9 (2)
C3—C4—C7—C8	175.79 (12)	C7—C4—C5—C6	179.10 (14)
C10—N2—C11—C12	109.92 (13)	C4—C5—C6—C1	0.7 (3)
C17—C12—C11—N2	104.01 (14)	C16—C15—C14—C13	0.0 (3)
C13—C12—C11—N2	−76.26 (15)	C12—C13—C14—C15	0.0 (2)
C11—N2—C10—O1	−7.34 (18)	C3—C2—C1—C6	0.4 (2)
C11—N2—C10—C8	171.11 (10)	C5—C6—C1—C2	−0.5 (3)
C7—C8—C10—O1	7.69 (17)	C14—C15—C16—C17	0.0 (3)
C9—C8—C10—O1	−172.55 (11)	C12—C17—C16—C15	0.1 (3)
C7—C8—C10—N2	−170.82 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H4···N1i	0.88 (1)	2.24 (1)	3.0687 (14)	157.(1)
C3—H3···O1ii	0.93	2.36	3.2672 (16)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H4⋯N1i	0.88 (1)	2.24 (1)	3.0687 (14)	157 (1)
C3—H3⋯O1ii	0.93	2.36	3.2672 (16)	164

Symmetry codes: (i) ; (ii) .