(E)-2-(2-Formyl-phen-oxy-meth-yl)-3-phenyl-prop-2-ene-nitrile.

In the title compound, C(17)H(13)NO(2), the dihedral angle between the benzene and the phenyl ring is 65.92 (7)°. The carbonitrile side chain is almost linear, the C-C-N angle being 175.55 (14)°. The crystal structure is stabilized by inter-molecular C-H⋯O inter-actions.

Related literature

For background to the synthesis, see: Bakthadoss & Murugan (2010 ▶). For a related structure, see: Jasinski et al. (2011 ▶).

Experimental

Crystal data

C17H13NO2

M = 263.28

Triclinic,

a = 8.0157 (4) Å

b = 9.2589 (4) Å

c = 10.2348 (5) Å

α = 68.283 (2)°

β = 73.432 (2)°

γ = 79.804 (2)°

V = 674.20 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.25 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

12600 measured reflections

2628 independent reflections

2162 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.03

2628 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811025670/pv2417sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025670/pv2417Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025670/pv2417Isup3.cml

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

C17H13NO2	Z = 2
Mr = 263.28	F(000) = 276
Triclinic, P1	Dx = 1.297 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0157 (4) Å	Cell parameters from 2628 reflections
b = 9.2589 (4) Å	θ = 1.0–26.0°
c = 10.2348 (5) Å	µ = 0.09 mm−1
α = 68.283 (2)°	T = 293 K
β = 73.432 (2)°	Block, colourless
γ = 79.804 (2)°	0.30 × 0.25 × 0.25 mm
V = 674.20 (6) Å3

Bruker Kappa APEXII CCD diffractometer	2162 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
graphite	θmax = 26.0°, θmin = 2.6°
ω scans	h = −9→9
12600 measured reflections	k = −11→11
2628 independent reflections	l = −12→12

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0528P)2 + 0.0828P] where P = (Fo2 + 2Fc2)/3
2628 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.17 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
C1	0.26890 (18)	0.64113 (15)	0.64335 (14)	0.0532 (3)
H1	0.3008	0.6132	0.7305	0.064*
C2	0.2241 (2)	0.79493 (15)	0.57315 (15)	0.0595 (4)
H2	0.2270	0.8700	0.6125	0.071*
C3	0.17519 (19)	0.83824 (15)	0.44570 (16)	0.0602 (4)
H3	0.1450	0.9425	0.3981	0.072*
C4	0.1710 (2)	0.72668 (16)	0.38826 (16)	0.0648 (4)
H4	0.1372	0.7556	0.3017	0.078*
C5	0.21649 (18)	0.57237 (15)	0.45793 (15)	0.0570 (3)
H5	0.2129	0.4980	0.4180	0.068*
C6	0.26761 (15)	0.52628 (13)	0.58692 (13)	0.0449 (3)
C7	0.31669 (16)	0.36612 (13)	0.66887 (13)	0.0468 (3)
H7	0.3373	0.3542	0.7574	0.056*
C8	0.33774 (15)	0.23310 (13)	0.64123 (13)	0.0462 (3)
C9	0.31738 (18)	0.22202 (14)	0.51102 (15)	0.0543 (3)
C10	0.38224 (15)	0.08068 (13)	0.74939 (14)	0.0486 (3)
H10A	0.4728	0.0193	0.7021	0.058*
H10B	0.4233	0.0975	0.8227	0.058*
C11	0.23087 (14)	−0.14432 (12)	0.91208 (12)	0.0385 (3)
C12	0.37770 (16)	−0.21887 (14)	0.96098 (14)	0.0496 (3)
H12	0.4804	−0.1690	0.9277	0.059*
C13	0.37016 (19)	−0.36785 (15)	1.05952 (15)	0.0582 (4)
H13	0.4686	−0.4175	1.0935	0.070*
C14	0.2212 (2)	−0.44558 (15)	1.10927 (14)	0.0586 (4)
H14	0.2196	−0.5474	1.1741	0.070*
C15	0.07545 (17)	−0.37049 (14)	1.06170 (13)	0.0497 (3)
H15	−0.0262	−0.4218	1.0954	0.060*
C16	0.07657 (14)	−0.21887 (13)	0.96393 (11)	0.0395 (3)
C17	−0.08123 (16)	−0.14054 (16)	0.91668 (14)	0.0534 (3)
H17	−0.0751	−0.0399	0.8497	0.064*
N1	0.3060 (2)	0.20353 (14)	0.40992 (15)	0.0774 (4)
O1	0.22458 (10)	0.00245 (9)	0.81342 (9)	0.0484 (2)
O2	−0.21885 (12)	−0.19734 (13)	0.95850 (12)	0.0737 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0663 (8)	0.0489 (7)	0.0454 (7)	−0.0121 (6)	−0.0079 (6)	−0.0176 (6)
C2	0.0776 (10)	0.0449 (7)	0.0588 (8)	−0.0084 (6)	−0.0097 (7)	−0.0244 (6)
C3	0.0708 (9)	0.0423 (7)	0.0632 (9)	0.0010 (6)	−0.0138 (7)	−0.0173 (6)
C4	0.0848 (11)	0.0519 (8)	0.0624 (9)	0.0057 (7)	−0.0312 (8)	−0.0195 (7)
C5	0.0736 (9)	0.0456 (7)	0.0589 (8)	−0.0028 (6)	−0.0204 (7)	−0.0230 (6)
C6	0.0463 (7)	0.0423 (6)	0.0428 (6)	−0.0110 (5)	−0.0012 (5)	−0.0145 (5)
C7	0.0499 (7)	0.0448 (6)	0.0421 (6)	−0.0128 (5)	−0.0041 (5)	−0.0117 (5)
C8	0.0454 (7)	0.0422 (6)	0.0461 (7)	−0.0110 (5)	−0.0023 (5)	−0.0124 (5)
C9	0.0643 (8)	0.0384 (6)	0.0577 (8)	−0.0074 (6)	−0.0094 (6)	−0.0158 (6)
C10	0.0411 (7)	0.0437 (6)	0.0548 (7)	−0.0100 (5)	−0.0047 (5)	−0.0119 (5)
C11	0.0407 (6)	0.0357 (5)	0.0382 (6)	−0.0023 (4)	−0.0092 (5)	−0.0121 (5)
C12	0.0421 (7)	0.0504 (7)	0.0583 (8)	0.0000 (5)	−0.0167 (6)	−0.0189 (6)
C13	0.0644 (9)	0.0514 (7)	0.0619 (8)	0.0136 (6)	−0.0308 (7)	−0.0193 (6)
C14	0.0839 (10)	0.0380 (6)	0.0495 (7)	0.0008 (6)	−0.0211 (7)	−0.0087 (5)
C15	0.0609 (8)	0.0451 (6)	0.0419 (6)	−0.0154 (6)	−0.0047 (6)	−0.0139 (5)
C16	0.0416 (6)	0.0421 (6)	0.0358 (6)	−0.0063 (5)	−0.0073 (5)	−0.0145 (5)
C17	0.0436 (7)	0.0618 (8)	0.0535 (7)	−0.0085 (6)	−0.0120 (6)	−0.0159 (6)
N1	0.1142 (12)	0.0570 (7)	0.0704 (9)	−0.0038 (7)	−0.0291 (8)	−0.0284 (7)
O1	0.0401 (5)	0.0395 (4)	0.0557 (5)	−0.0078 (3)	−0.0119 (4)	−0.0026 (4)
O2	0.0447 (6)	0.1005 (8)	0.0789 (7)	−0.0212 (5)	−0.0146 (5)	−0.0272 (6)

C1—C2	1.3719 (18)	C10—O1	1.4324 (13)
C1—C6	1.3879 (17)	C10—H10A	0.9700
C1—H1	0.9300	C10—H10B	0.9700
C2—C3	1.3656 (19)	C11—O1	1.3631 (13)
C2—H2	0.9300	C11—C12	1.3802 (16)
C3—C4	1.3735 (19)	C11—C16	1.3945 (15)
C3—H3	0.9300	C12—C13	1.3743 (18)
C4—C5	1.3758 (18)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.374 (2)
C5—C6	1.3865 (17)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.3684 (19)
C6—C7	1.4555 (17)	C14—H14	0.9300
C7—C8	1.3351 (16)	C15—C16	1.3900 (16)
C7—H7	0.9300	C15—H15	0.9300
C8—C9	1.4298 (19)	C16—C17	1.4575 (17)
C8—C10	1.4950 (17)	C17—O2	1.2026 (15)
C9—N1	1.1397 (17)	C17—H17	0.9300
C2—C1—C6	121.36 (12)	C8—C10—H10A	110.5
C2—C1—H1	119.3	O1—C10—H10B	110.5
C6—C1—H1	119.3	C8—C10—H10B	110.5
C3—C2—C1	120.28 (12)	H10A—C10—H10B	108.7
C3—C2—H2	119.9	O1—C11—C12	123.92 (10)
C1—C2—H2	119.9	O1—C11—C16	115.88 (9)
C2—C3—C4	119.54 (12)	C12—C11—C16	120.20 (10)
C2—C3—H3	120.2	C13—C12—C11	119.10 (12)
C4—C3—H3	120.2	C13—C12—H12	120.4
C3—C4—C5	120.40 (13)	C11—C12—H12	120.4
C3—C4—H4	119.8	C14—C13—C12	121.87 (12)
C5—C4—H4	119.8	C14—C13—H13	119.1
C4—C5—C6	120.90 (12)	C12—C13—H13	119.1
C4—C5—H5	119.6	C15—C14—C13	118.78 (12)
C6—C5—H5	119.6	C15—C14—H14	120.6
C5—C6—C1	117.51 (11)	C13—C14—H14	120.6
C5—C6—C7	124.85 (11)	C14—C15—C16	121.20 (12)
C1—C6—C7	117.62 (11)	C14—C15—H15	119.4
C8—C7—C6	132.27 (12)	C16—C15—H15	119.4
C8—C7—H7	113.9	C15—C16—C11	118.81 (11)
C6—C7—H7	113.9	C15—C16—C17	120.15 (11)
C7—C8—C9	124.29 (11)	C11—C16—C17	121.04 (10)
C7—C8—C10	121.16 (11)	O2—C17—C16	124.38 (12)
C9—C8—C10	114.54 (10)	O2—C17—H17	117.8
N1—C9—C8	175.55 (14)	C16—C17—H17	117.8
O1—C10—C8	106.15 (9)	C11—O1—C10	118.29 (9)
O1—C10—H10A	110.5
C6—C1—C2—C3	0.6 (2)	C16—C11—C12—C13	0.92 (18)
C1—C2—C3—C4	0.1 (2)	C11—C12—C13—C14	0.9 (2)
C2—C3—C4—C5	−0.3 (2)	C12—C13—C14—C15	−1.7 (2)
C3—C4—C5—C6	−0.1 (2)	C13—C14—C15—C16	0.54 (19)
C4—C5—C6—C1	0.8 (2)	C14—C15—C16—C11	1.25 (17)
C4—C5—C6—C7	179.50 (13)	C14—C15—C16—C17	−179.03 (11)
C2—C1—C6—C5	−1.04 (19)	O1—C11—C16—C15	178.18 (10)
C2—C1—C6—C7	−179.87 (11)	C12—C11—C16—C15	−1.98 (16)
C5—C6—C7—C8	5.5 (2)	O1—C11—C16—C17	−1.54 (16)
C1—C6—C7—C8	−175.73 (13)	C12—C11—C16—C17	178.30 (11)
C6—C7—C8—C9	1.5 (2)	C15—C16—C17—O2	1.27 (19)
C6—C7—C8—C10	−177.29 (12)	C11—C16—C17—O2	−179.01 (12)
C7—C8—C10—O1	104.09 (13)	C12—C11—O1—C10	4.17 (16)
C9—C8—C10—O1	−74.78 (13)	C16—C11—O1—C10	−175.99 (9)
O1—C11—C12—C13	−179.25 (11)	C8—C10—O1—C11	176.89 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2i	0.93	2.48	3.2675 (17)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2i	0.93	2.48	3.2675 (17)	143

Symmetry code: (i) .