(E)-2-[(2-Formyl-phen-oxy)meth-yl]-3-(4-methyl-phen-yl)prop-2-ene-nitrile.

In the title compound, C(18)H(15)NO(2), the dihedral angle between the two benzene rings is 74.8 (1)°. The carbonitrile chain is almost linear, the C-C-N angle being 176.2 (2)°. In the crystal, π-π inter-actions [centroid-centroid distance = 3.842 (1) Å] are observed.

Related literature

For background to the synthetic procedure, see: Bakthadoss & Murugan (2010 ▶). For related structures, see: Swaminathan et al. (2011 ▶); Prasanna et al. (2011 ▶).

Experimental

Crystal data

C18H15NO2

M = 277.31

Monoclinic,

a = 7.0792 (4) Å

b = 13.7006 (7) Å

c = 15.3587 (9) Å

β = 96.782 (2)°

V = 1479.21 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.23 × 0.21 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.982, T max = 0.988

15027 measured reflections

3321 independent reflections

1950 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.133

S = 1.01

3321 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811051415/im2342sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051415/im2342Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811051415/im2342Isup3.cml

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

C18H15NO2	F(000) = 584
Mr = 277.31	Dx = 1.245 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3403 reflections
a = 7.0792 (4) Å	θ = 2.0–27.5°
b = 13.7006 (7) Å	µ = 0.08 mm−1
c = 15.3587 (9) Å	T = 293 K
β = 96.782 (2)°	Block, yellow
V = 1479.21 (14) Å3	0.23 × 0.21 × 0.15 mm
Z = 4

Bruker APEXII CCD diffractometer	3321 independent reflections
Radiation source: fine-focus sealed tube	1950 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 2.0°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −17→17
Tmin = 0.982, Tmax = 0.988	l = −19→19
15027 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0553P)2 + 0.2089P] where P = (Fo2 + 2Fc2)/3
3321 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.6118 (2)	0.26454 (11)	0.25898 (11)	0.0828 (5)
O1	0.2658 (2)	0.23139 (12)	−0.09622 (11)	0.1133 (5)
O2	0.25632 (15)	0.38860 (8)	0.11791 (7)	0.0726 (3)
C1	0.0835 (2)	0.37959 (11)	0.06904 (11)	0.0621 (4)
C2	−0.0823 (2)	0.42103 (13)	0.09048 (12)	0.0750 (5)
H2	−0.0825	0.4565	0.1421	0.090*
C3	−0.2478 (2)	0.40934 (15)	0.03456 (14)	0.0856 (6)
H3	−0.3599	0.4372	0.0489	0.103*
C4	−0.2505 (3)	0.35721 (16)	−0.04214 (14)	0.0879 (6)
H4	−0.3631	0.3502	−0.0794	0.105*
C5	−0.0866 (3)	0.31602 (14)	−0.06293 (12)	0.0777 (5)
H5	−0.0879	0.2812	−0.1150	0.093*
C6	0.0820 (2)	0.32522 (11)	−0.00780 (11)	0.0648 (4)
C7	0.2538 (3)	0.27629 (15)	−0.02978 (14)	0.0846 (5)
H7	0.3621	0.2802	0.0107	0.101*
C8	0.2646 (2)	0.43560 (13)	0.20139 (11)	0.0716 (5)
H8A	0.1879	0.4003	0.2392	0.086*
H8B	0.2167	0.5018	0.1945	0.086*
C9	0.4680 (2)	0.43625 (11)	0.24015 (10)	0.0627 (4)
C10	0.5640 (2)	0.51893 (12)	0.25968 (10)	0.0691 (5)
H10	0.4965	0.5755	0.2432	0.083*
C11	0.7555 (2)	0.53562 (11)	0.30210 (10)	0.0645 (4)
C12	0.8639 (3)	0.46728 (13)	0.35274 (12)	0.0802 (5)
H12	0.8151	0.4051	0.3595	0.096*
C13	1.0416 (3)	0.49015 (14)	0.39295 (13)	0.0867 (6)
H13	1.1104	0.4430	0.4268	0.104*
C14	1.1218 (3)	0.58109 (14)	0.38479 (12)	0.0775 (5)
C15	1.0151 (3)	0.64806 (14)	0.33374 (14)	0.0858 (6)
H15	1.0656	0.7097	0.3260	0.103*
C16	0.8365 (3)	0.62670 (12)	0.29389 (13)	0.0799 (5)
H16	0.7680	0.6744	0.2606	0.096*
C17	0.5526 (2)	0.34163 (12)	0.25245 (11)	0.0626 (4)
C18	1.3145 (3)	0.60602 (18)	0.43169 (16)	0.1045 (7)
H18A	1.3777	0.6508	0.3967	0.157*
H18B	1.3890	0.5476	0.4411	0.157*
H18C	1.2998	0.6356	0.4872	0.157*

	U11	U22	U33	U12	U13	U23
N1	0.0778 (10)	0.0609 (9)	0.1058 (12)	−0.0005 (7)	−0.0062 (8)	−0.0046 (8)
O1	0.1137 (12)	0.1266 (12)	0.1033 (12)	−0.0130 (9)	0.0288 (9)	−0.0442 (10)
O2	0.0653 (7)	0.0851 (8)	0.0650 (7)	0.0095 (5)	−0.0017 (5)	−0.0154 (6)
C1	0.0592 (9)	0.0628 (9)	0.0630 (10)	−0.0010 (7)	0.0026 (8)	0.0060 (8)
C2	0.0696 (11)	0.0788 (11)	0.0761 (12)	0.0068 (8)	0.0068 (9)	0.0040 (9)
C3	0.0615 (11)	0.0977 (14)	0.0965 (15)	0.0056 (9)	0.0051 (10)	0.0173 (12)
C4	0.0681 (12)	0.1052 (15)	0.0864 (14)	−0.0147 (10)	−0.0076 (10)	0.0145 (12)
C5	0.0758 (12)	0.0859 (12)	0.0700 (12)	−0.0228 (9)	0.0022 (9)	0.0022 (9)
C6	0.0651 (10)	0.0634 (9)	0.0656 (10)	−0.0123 (7)	0.0067 (8)	0.0028 (8)
C7	0.0784 (12)	0.0901 (13)	0.0856 (14)	−0.0107 (10)	0.0112 (10)	−0.0195 (11)
C8	0.0733 (10)	0.0748 (11)	0.0655 (11)	0.0118 (8)	0.0038 (8)	−0.0101 (8)
C9	0.0720 (10)	0.0596 (9)	0.0554 (9)	0.0067 (7)	0.0026 (7)	−0.0061 (7)
C10	0.0839 (11)	0.0567 (9)	0.0656 (10)	0.0108 (8)	0.0037 (9)	−0.0036 (8)
C11	0.0798 (11)	0.0495 (8)	0.0640 (10)	0.0044 (7)	0.0078 (8)	−0.0086 (7)
C12	0.1049 (14)	0.0552 (9)	0.0741 (11)	−0.0040 (9)	−0.0157 (10)	−0.0031 (8)
C13	0.1041 (14)	0.0701 (11)	0.0791 (13)	0.0091 (10)	−0.0170 (11)	−0.0103 (9)
C14	0.0785 (11)	0.0775 (12)	0.0773 (12)	0.0015 (9)	0.0130 (9)	−0.0236 (10)
C15	0.0853 (13)	0.0634 (11)	0.1111 (16)	−0.0060 (9)	0.0212 (12)	−0.0088 (11)
C16	0.0834 (12)	0.0572 (10)	0.0991 (14)	0.0075 (8)	0.0105 (10)	0.0000 (9)
C17	0.0622 (9)	0.0593 (10)	0.0650 (10)	−0.0037 (7)	0.0013 (7)	−0.0061 (8)
C18	0.0862 (14)	0.1194 (17)	0.1068 (17)	−0.0062 (12)	0.0066 (12)	−0.0322 (14)

N1—C17	1.1362 (19)	C9—C10	1.337 (2)
O1—C7	1.203 (2)	C9—C17	1.431 (2)
O2—C1	1.3634 (17)	C10—C11	1.451 (2)
O2—C8	1.4297 (19)	C10—H10	0.9300
C1—C2	1.378 (2)	C11—C16	1.385 (2)
C1—C6	1.395 (2)	C11—C12	1.389 (2)
C2—C3	1.378 (2)	C12—C13	1.371 (2)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.376 (3)	C13—C14	1.381 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.362 (3)	C14—C15	1.374 (3)
C4—H4	0.9300	C14—C18	1.505 (3)
C5—C6	1.385 (2)	C15—C16	1.370 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.462 (3)	C16—H16	0.9300
C7—H7	0.9300	C18—H18A	0.9600
C8—C9	1.492 (2)	C18—H18B	0.9600
C8—H8A	0.9700	C18—H18C	0.9600
C8—H8B	0.9700
C1—O2—C8	118.26 (12)	C17—C9—C8	114.60 (13)
O2—C1—C2	124.43 (15)	C9—C10—C11	131.12 (15)
O2—C1—C6	115.50 (14)	C9—C10—H10	114.4
C2—C1—C6	120.06 (15)	C11—C10—H10	114.4
C3—C2—C1	119.25 (18)	C16—C11—C12	116.81 (16)
C3—C2—H2	120.4	C16—C11—C10	118.41 (15)
C1—C2—H2	120.4	C12—C11—C10	124.76 (16)
C4—C3—C2	121.25 (18)	C13—C12—C11	121.01 (17)
C4—C3—H3	119.4	C13—C12—H12	119.5
C2—C3—H3	119.4	C11—C12—H12	119.5
C5—C4—C3	119.34 (17)	C12—C13—C14	122.04 (18)
C5—C4—H4	120.3	C12—C13—H13	119.0
C3—C4—H4	120.3	C14—C13—H13	119.0
C4—C5—C6	121.04 (18)	C15—C14—C13	116.75 (18)
C4—C5—H5	119.5	C15—C14—C18	121.87 (19)
C6—C5—H5	119.5	C13—C14—C18	121.36 (19)
C5—C6—C1	119.04 (16)	C16—C15—C14	121.92 (18)
C5—C6—C7	119.82 (17)	C16—C15—H15	119.0
C1—C6—C7	121.13 (15)	C14—C15—H15	119.0
O1—C7—C6	125.05 (18)	C15—C16—C11	121.46 (17)
O1—C7—H7	117.5	C15—C16—H16	119.3
C6—C7—H7	117.5	C11—C16—H16	119.3
O2—C8—C9	107.21 (13)	N1—C17—C9	176.18 (17)
O2—C8—H8A	110.3	C14—C18—H18A	109.5
C9—C8—H8A	110.3	C14—C18—H18B	109.5
O2—C8—H8B	110.3	H18A—C18—H18B	109.5
C9—C8—H8B	110.3	C14—C18—H18C	109.5
H8A—C8—H8B	108.5	H18A—C18—H18C	109.5
C10—C9—C17	122.98 (14)	H18B—C18—H18C	109.5
C10—C9—C8	122.40 (14)
C8—O2—C1—C2	6.6 (2)	O2—C8—C9—C17	−59.52 (19)
C8—O2—C1—C6	−174.26 (14)	C17—C9—C10—C11	−6.1 (3)
O2—C1—C2—C3	178.05 (15)	C8—C9—C10—C11	175.59 (16)
C6—C1—C2—C3	−1.0 (2)	C9—C10—C11—C16	163.39 (19)
C1—C2—C3—C4	0.0 (3)	C9—C10—C11—C12	−18.2 (3)
C2—C3—C4—C5	0.3 (3)	C16—C11—C12—C13	0.6 (3)
C3—C4—C5—C6	0.5 (3)	C10—C11—C12—C13	−177.83 (17)
C4—C5—C6—C1	−1.5 (3)	C11—C12—C13—C14	−0.5 (3)
C4—C5—C6—C7	177.08 (18)	C12—C13—C14—C15	−0.4 (3)
O2—C1—C6—C5	−177.37 (13)	C12—C13—C14—C18	178.02 (19)
C2—C1—C6—C5	1.8 (2)	C13—C14—C15—C16	1.1 (3)
O2—C1—C6—C7	4.1 (2)	C18—C14—C15—C16	−177.31 (19)
C2—C1—C6—C7	−176.79 (16)	C14—C15—C16—C11	−1.0 (3)
C5—C6—C7—O1	4.5 (3)	C12—C11—C16—C15	0.1 (3)
C1—C6—C7—O1	−176.95 (19)	C10—C11—C16—C15	178.63 (17)
C1—O2—C8—C9	−179.60 (13)	C10—C9—C17—N1	−160 (3)
O2—C8—C9—C10	118.94 (17)	C8—C9—C17—N1	19 (3)