2-[(E)-1-(4-Meth-oxy-phen-yl)pent-1-en-3-yl-idene]malononitrile.

In the title compound, C(15)H(14)N(2)O, the mol-ecule skeleton displays an approximately planar structure except for the ethyl group [maximum deviation = 0.042 (1) Å]. The meth-oxy-phenyl ring and butanylidenemalononitrile groups are located on opposite sides of the C=C bond, showing an E configuration. Weak inter-molecular C-H⋯N hydrogen bonding is present in the crystal structure.

Related literature

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

Experimental

Crystal data

C15H14N2O

M = 238.28

Monoclinic,

a = 12.3371 (3) Å

b = 8.8832 (2) Å

c = 12.8554 (3) Å

β = 108.050 (2)°

V = 1339.53 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.60 mm−1

T = 291 K

0.42 × 0.40 × 0.36 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.787, T max = 0.813

9020 measured reflections

2456 independent reflections

2266 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.112

S = 1.05

2456 reflections

165 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.14 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/S1600536810045381/xu5082sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045381/xu5082Isup2.hkl

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

C15H14N2O	F(000) = 504
Mr = 238.28	Dx = 1.182 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 6882 reflections
a = 12.3371 (3) Å	θ = 3.6–69.4°
b = 8.8832 (2) Å	µ = 0.60 mm−1
c = 12.8554 (3) Å	T = 291 K
β = 108.050 (2)°	Block, yellow
V = 1339.53 (5) Å3	0.42 × 0.40 × 0.36 mm
Z = 4

Oxford Diffraction Gemini S Ultra diffractometer	2456 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2266 reflections with I > 2σ(I)
mirror	Rint = 0.014
Detector resolution: 15.9149 pixels mm-1	θmax = 69.6°, θmin = 4.3°
ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −10→10
Tmin = 0.787, Tmax = 0.813	l = −15→8
9020 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0607P)2 + 0.1456P] where P = (Fo2 + 2Fc2)/3
2456 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.11 e Å−3
3 restraints	Δρmin = −0.14 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	0.09486 (7)	−0.22305 (10)	0.03379 (7)	0.0668 (3)
C14	−0.13644 (11)	0.27243 (16)	0.51588 (10)	0.0646 (3)
C7	0.13090 (9)	0.13033 (12)	0.40443 (8)	0.0486 (3)
H7	0.2053	0.1581	0.4428	0.058*
C2	−0.00061 (9)	−0.10045 (13)	0.15020 (9)	0.0534 (3)
H2	−0.0720	−0.1348	0.1083	0.064*
C8	0.04916 (9)	0.17842 (13)	0.44506 (8)	0.0505 (3)
H8	−0.0254	0.1492	0.4090	0.061*
C4	0.11576 (9)	0.03969 (11)	0.30705 (8)	0.0464 (3)
C5	0.21124 (9)	0.00232 (14)	0.27569 (10)	0.0559 (3)
H5	0.2828	0.0364	0.3174	0.067*
C1	0.09578 (9)	−0.13673 (12)	0.12143 (9)	0.0512 (3)
C3	0.01045 (9)	−0.01297 (13)	0.24151 (9)	0.0525 (3)
H3	−0.0546	0.0117	0.2599	0.063*
C6	0.20146 (9)	−0.08369 (14)	0.18453 (10)	0.0611 (3)
H6	0.2661	−0.1066	0.1649	0.073*
C9	0.06860 (9)	0.27216 (12)	0.54059 (9)	0.0507 (3)
N1	−0.22774 (11)	0.23824 (19)	0.46897 (11)	0.0962 (5)
C12	−0.02183 (10)	0.31596 (13)	0.57378 (9)	0.0552 (3)
N2	−0.00312 (13)	0.48196 (17)	0.74197 (12)	0.0955 (4)
C10	0.18745 (10)	0.31909 (15)	0.60535 (10)	0.0640 (3)
H10A	0.1837	0.4087	0.6472	0.077*
H10B	0.2297	0.3441	0.5554	0.077*
C15	−0.01196 (12)	−0.28321 (15)	−0.03201 (11)	0.0687 (4)
H15A	−0.0445	−0.3435	0.0128	0.103*
H15B	−0.0002	−0.3444	−0.0891	0.103*
H15C	−0.0629	−0.2022	−0.0638	0.103*
C13	−0.00959 (11)	0.40823 (15)	0.66777 (11)	0.0670 (3)
C11	0.25010 (13)	0.1964 (2)	0.68261 (12)	0.0890 (5)
H11A	0.2143	0.1807	0.7382	0.133*
H11B	0.3280	0.2260	0.7161	0.133*
H11C	0.2477	0.1047	0.6424	0.133*

	U11	U22	U33	U12	U13	U23
O1	0.0564 (5)	0.0802 (6)	0.0658 (5)	0.0005 (4)	0.0219 (4)	−0.0264 (4)
C14	0.0545 (6)	0.0853 (9)	0.0560 (7)	0.0201 (5)	0.0199 (5)	0.0060 (5)
C7	0.0477 (5)	0.0515 (6)	0.0483 (5)	−0.0039 (4)	0.0173 (4)	−0.0007 (4)
C2	0.0417 (5)	0.0614 (6)	0.0569 (6)	−0.0034 (5)	0.0150 (4)	−0.0094 (5)
C8	0.0483 (6)	0.0564 (6)	0.0481 (6)	0.0002 (4)	0.0167 (4)	−0.0022 (5)
C4	0.0451 (5)	0.0490 (5)	0.0476 (5)	−0.0006 (4)	0.0179 (4)	0.0000 (4)
C5	0.0405 (5)	0.0666 (7)	0.0609 (6)	−0.0030 (5)	0.0163 (5)	−0.0113 (5)
C1	0.0505 (6)	0.0527 (6)	0.0526 (6)	0.0020 (5)	0.0194 (5)	−0.0070 (5)
C3	0.0426 (5)	0.0620 (6)	0.0576 (6)	−0.0014 (5)	0.0225 (5)	−0.0076 (5)
C6	0.0444 (6)	0.0742 (8)	0.0697 (7)	0.0008 (5)	0.0250 (5)	−0.0176 (6)
C9	0.0556 (6)	0.0511 (6)	0.0487 (6)	0.0024 (4)	0.0209 (5)	0.0016 (4)
N1	0.0536 (7)	0.1471 (13)	0.0840 (8)	0.0179 (7)	0.0154 (6)	0.0044 (8)
C12	0.0588 (6)	0.0598 (6)	0.0503 (6)	0.0116 (5)	0.0215 (5)	0.0034 (4)
N2	0.1005 (10)	0.1055 (10)	0.0906 (9)	0.0068 (8)	0.0443 (8)	−0.0336 (8)
C10	0.0619 (7)	0.0708 (7)	0.0652 (7)	−0.0132 (6)	0.0284 (6)	−0.0197 (6)
C15	0.0699 (8)	0.0710 (8)	0.0633 (7)	−0.0060 (6)	0.0179 (6)	−0.0210 (6)
C13	0.0705 (8)	0.0706 (8)	0.0664 (7)	0.0122 (6)	0.0308 (6)	−0.0064 (6)
C11	0.0617 (8)	0.1201 (13)	0.0720 (9)	−0.0096 (8)	0.0015 (7)	−0.0004 (9)

O1—C1	1.3600 (13)	C1—C6	1.3873 (15)
O1—C15	1.4308 (15)	C3—H3	0.9300
C14—N1	1.1417 (18)	C6—H6	0.9300
C14—C12	1.4321 (18)	C9—C12	1.3686 (15)
C7—C8	1.3412 (15)	C9—C10	1.5035 (16)
C7—C4	1.4510 (14)	C12—C13	1.4289 (16)
C7—H7	0.9300	N2—C13	1.1393 (17)
C2—C3	1.3788 (15)	C10—C11	1.516 (2)
C2—C1	1.3883 (14)	C10—H10A	0.9700
C2—H2	0.9300	C10—H10B	0.9700
C8—C9	1.4410 (15)	C15—H15A	0.9600
C8—H8	0.9300	C15—H15B	0.9600
C4—C3	1.3923 (15)	C15—H15C	0.9600
C4—C5	1.3980 (15)	C11—H11A	0.9600
C5—C6	1.3727 (16)	C11—H11B	0.9600
C5—H5	0.9300	C11—H11C	0.9600
C1—O1—C15	118.04 (9)	C12—C9—C8	119.57 (10)
N1—C14—C12	179.45 (15)	C12—C9—C10	119.86 (10)
C8—C7—C4	126.97 (10)	C8—C9—C10	120.56 (9)
C8—C7—H7	116.5	C9—C12—C13	122.96 (11)
C4—C7—H7	116.5	C9—C12—C14	122.01 (11)
C3—C2—C1	119.38 (10)	C13—C12—C14	115.03 (10)
C3—C2—H2	120.3	C9—C10—C11	112.04 (11)
C1—C2—H2	120.3	C9—C10—H10A	109.2
C7—C8—C9	124.70 (10)	C11—C10—H10A	109.2
C7—C8—H8	117.7	C9—C10—H10B	109.2
C9—C8—H8	117.7	C11—C10—H10B	109.2
C3—C4—C5	117.22 (10)	H10A—C10—H10B	107.9
C3—C4—C7	123.72 (9)	O1—C15—H15A	109.5
C5—C4—C7	119.06 (10)	O1—C15—H15B	109.5
C6—C5—C4	121.29 (10)	H15A—C15—H15B	109.5
C6—C5—H5	119.4	O1—C15—H15C	109.5
C4—C5—H5	119.4	H15A—C15—H15C	109.5
O1—C1—C6	116.17 (9)	H15B—C15—H15C	109.5
O1—C1—C2	124.31 (10)	N2—C13—C12	178.06 (14)
C6—C1—C2	119.53 (10)	C10—C11—H11A	109.5
C2—C3—C4	122.15 (9)	C10—C11—H11B	109.5
C2—C3—H3	118.9	H11A—C11—H11B	109.5
C4—C3—H3	118.9	C10—C11—H11C	109.5
C5—C6—C1	120.42 (10)	H11A—C11—H11C	109.5
C5—C6—H6	119.8	H11B—C11—H11C	109.5
C1—C6—H6	119.8
C4—C7—C8—C9	−178.09 (10)	C4—C5—C6—C1	−0.5 (2)
C8—C7—C4—C3	−1.00 (18)	O1—C1—C6—C5	−178.94 (11)
C8—C7—C4—C5	178.78 (11)	C2—C1—C6—C5	0.91 (19)
C3—C4—C5—C6	−0.49 (18)	C7—C8—C9—C12	179.18 (11)
C7—C4—C5—C6	179.72 (10)	C7—C8—C9—C10	−2.24 (17)
C15—O1—C1—C6	178.49 (11)	C8—C9—C12—C13	179.74 (10)
C15—O1—C1—C2	−1.35 (17)	C10—C9—C12—C13	1.14 (18)
C3—C2—C1—O1	179.44 (10)	C8—C9—C12—C14	−0.48 (18)
C3—C2—C1—C6	−0.40 (18)	C10—C9—C12—C14	−179.08 (11)
C1—C2—C3—C4	−0.58 (18)	C12—C9—C10—C11	98.07 (14)
C5—C4—C3—C2	1.01 (17)	C8—C9—C10—C11	−80.51 (14)
C7—C4—C3—C2	−179.20 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N1i	0.93	2.62	3.5285 (19)	167 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N1i	0.93	2.62	3.5285 (19)	167 (1)

Symmetry code: (i) .