(E)-3-(2-Chloro-phen-yl)-2-[(2-formylphen-oxy)meth-yl]prop-2-ene-nitrile.

In the title compound, C(17)H(12)ClNO(2), the dihedral angle between the two benzene rings is 42.9 (1)°. There are no sgnificant inter-molecular inter-actions.

Related literature

For background to the synthetic procedure, see: Bakthadoss & Murugan (2010 ▶). For related structures, see: Manikandan et al. (2012 ▶); Prasanna et al. (2011 ▶).

Experimental

Crystal data

C17H12ClNO2

M = 297.73

Triclinic,

a = 7.5022 (4) Å

b = 7.8301 (4) Å

c = 13.2379 (8) Å

α = 75.470 (3)°

β = 84.696 (2)°

γ = 70.935 (2)°

V = 711.43 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.24 × 0.21 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.937, T max = 0.960

14438 measured reflections

3433 independent reflections

2685 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.114

S = 1.04

3433 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.19 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/S1600536812008410/bt5830sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008410/bt5830Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008410/bt5830Isup3.cml

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

C17H12ClNO2	Z = 2
Mr = 297.73	F(000) = 308
Triclinic, P1	Dx = 1.390 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5022 (4) Å	Cell parameters from 3463 reflections
b = 7.8301 (4) Å	θ = 2.8–28.1°
c = 13.2379 (8) Å	µ = 0.27 mm−1
α = 75.470 (3)°	T = 293 K
β = 84.696 (2)°	Block, colourless
γ = 70.935 (2)°	0.24 × 0.21 × 0.15 mm
V = 711.43 (7) Å3

Bruker APEXII CCD diffractometer	3433 independent reflections
Radiation source: fine-focus sealed tube	2685 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 10.0 pixels mm-1	θmax = 28.1°, θmin = 2.8°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→10
Tmin = 0.937, Tmax = 0.960	l = −17→17
14438 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) = 0.114	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.053P)2 + 0.159P] where P = (Fo2 + 2Fc2)/3
3433 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.19 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
Cl1	0.31341 (8)	0.23140 (7)	0.01456 (3)	0.07011 (17)
N1	0.1141 (2)	−0.1357 (2)	0.40658 (12)	0.0660 (4)
O1	0.3876 (2)	−0.21291 (18)	0.75288 (10)	0.0765 (4)
O2	0.28615 (15)	0.15782 (13)	0.48411 (7)	0.0436 (2)
C1	0.32059 (19)	0.22280 (18)	0.56458 (10)	0.0364 (3)
C2	0.3173 (2)	0.4030 (2)	0.55536 (12)	0.0471 (4)
H2	0.2830	0.4913	0.4928	0.057*
C3	0.3655 (3)	0.4509 (2)	0.64002 (14)	0.0562 (4)
H3	0.3639	0.5724	0.6336	0.067*
C4	0.4160 (3)	0.3238 (2)	0.73390 (13)	0.0559 (4)
H4	0.4513	0.3578	0.7896	0.067*
C5	0.4132 (2)	0.1464 (2)	0.74357 (11)	0.0474 (4)
H5	0.4442	0.0603	0.8071	0.057*
C6	0.36463 (19)	0.09286 (18)	0.66019 (10)	0.0377 (3)
C7	0.3555 (2)	−0.0949 (2)	0.67304 (12)	0.0479 (4)
H7	0.3225	−0.1251	0.6153	0.057*
C8	0.1837 (2)	0.2928 (2)	0.39872 (11)	0.0428 (3)
H8A	0.2576	0.3715	0.3627	0.051*
H8B	0.0670	0.3705	0.4233	0.051*
C9	0.1425 (2)	0.1907 (2)	0.32654 (11)	0.0407 (3)
C10	0.1257 (2)	0.2525 (2)	0.22304 (11)	0.0453 (3)
H10	0.0988	0.1754	0.1876	0.054*
C11	0.1448 (2)	0.4273 (2)	0.15926 (11)	0.0450 (3)
C12	0.2291 (2)	0.4332 (2)	0.05996 (12)	0.0505 (4)
C13	0.2510 (3)	0.5949 (3)	−0.00219 (14)	0.0639 (5)
H13	0.3080	0.5953	−0.0676	0.077*
C14	0.1887 (3)	0.7543 (3)	0.03273 (17)	0.0725 (6)
H14	0.2040	0.8635	−0.0090	0.087*
C15	0.1029 (3)	0.7550 (3)	0.12961 (16)	0.0693 (5)
H15	0.0605	0.8643	0.1528	0.083*
C16	0.0804 (3)	0.5936 (2)	0.19183 (13)	0.0562 (4)
H16	0.0212	0.5955	0.2566	0.067*
C17	0.1252 (2)	0.0091 (2)	0.37263 (11)	0.0463 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.0911 (4)	0.0811 (3)	0.0395 (2)	−0.0294 (3)	0.0038 (2)	−0.0151 (2)
N1	0.0812 (11)	0.0554 (9)	0.0620 (9)	−0.0321 (8)	0.0090 (8)	−0.0041 (7)
O1	0.1249 (12)	0.0518 (7)	0.0519 (7)	−0.0394 (8)	−0.0187 (7)	0.0113 (6)
O2	0.0599 (6)	0.0349 (5)	0.0322 (5)	−0.0102 (4)	−0.0091 (4)	−0.0044 (4)
C1	0.0398 (7)	0.0358 (7)	0.0329 (6)	−0.0113 (5)	0.0013 (5)	−0.0083 (5)
C2	0.0612 (9)	0.0358 (7)	0.0424 (8)	−0.0170 (7)	0.0022 (7)	−0.0043 (6)
C3	0.0757 (11)	0.0435 (8)	0.0598 (10)	−0.0286 (8)	0.0056 (8)	−0.0197 (7)
C4	0.0689 (11)	0.0625 (10)	0.0472 (9)	−0.0272 (8)	0.0005 (7)	−0.0242 (8)
C5	0.0562 (9)	0.0514 (9)	0.0344 (7)	−0.0170 (7)	−0.0019 (6)	−0.0089 (6)
C6	0.0424 (7)	0.0352 (7)	0.0341 (7)	−0.0121 (6)	0.0002 (5)	−0.0062 (5)
C7	0.0610 (9)	0.0390 (8)	0.0421 (8)	−0.0176 (7)	−0.0056 (7)	−0.0025 (6)
C8	0.0504 (8)	0.0388 (7)	0.0339 (7)	−0.0099 (6)	−0.0036 (6)	−0.0037 (5)
C9	0.0417 (7)	0.0429 (7)	0.0354 (7)	−0.0138 (6)	0.0005 (5)	−0.0050 (6)
C10	0.0520 (8)	0.0507 (8)	0.0358 (7)	−0.0215 (7)	−0.0031 (6)	−0.0069 (6)
C11	0.0469 (8)	0.0512 (9)	0.0339 (7)	−0.0172 (7)	−0.0113 (6)	0.0017 (6)
C12	0.0520 (9)	0.0601 (10)	0.0358 (7)	−0.0200 (7)	−0.0105 (6)	0.0020 (7)
C13	0.0614 (10)	0.0752 (13)	0.0447 (9)	−0.0263 (9)	−0.0070 (8)	0.0132 (8)
C14	0.0733 (13)	0.0589 (12)	0.0736 (13)	−0.0287 (10)	−0.0198 (10)	0.0222 (10)
C15	0.0788 (13)	0.0479 (10)	0.0730 (13)	−0.0153 (9)	−0.0219 (10)	0.0017 (9)
C16	0.0621 (10)	0.0509 (9)	0.0478 (9)	−0.0124 (8)	−0.0107 (7)	−0.0013 (7)
C17	0.0510 (8)	0.0507 (9)	0.0366 (7)	−0.0191 (7)	0.0028 (6)	−0.0062 (6)

Cl1—C12	1.7353 (18)	C8—C9	1.499 (2)
N1—C17	1.137 (2)	C8—H8A	0.9700
O1—C7	1.2004 (18)	C8—H8B	0.9700
O2—C1	1.3672 (16)	C9—C10	1.3367 (19)
O2—C8	1.4199 (16)	C9—C17	1.443 (2)
C1—C2	1.378 (2)	C10—C11	1.460 (2)
C1—C6	1.3992 (18)	C10—H10	0.9300
C2—C3	1.379 (2)	C11—C16	1.395 (2)
C2—H2	0.9300	C11—C12	1.402 (2)
C3—C4	1.378 (2)	C12—C13	1.376 (2)
C3—H3	0.9300	C13—C14	1.364 (3)
C4—C5	1.369 (2)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.381 (3)
C5—C6	1.390 (2)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.377 (3)
C6—C7	1.460 (2)	C15—H15	0.9300
C7—H7	0.9300	C16—H16	0.9300
C1—O2—C8	116.56 (10)	H8A—C8—H8B	108.5
O2—C1—C2	123.98 (12)	C10—C9—C17	117.74 (14)
O2—C1—C6	115.96 (11)	C10—C9—C8	125.17 (13)
C2—C1—C6	120.05 (13)	C17—C9—C8	117.06 (12)
C1—C2—C3	119.14 (14)	C9—C10—C11	127.43 (14)
C1—C2—H2	120.4	C9—C10—H10	116.3
C3—C2—H2	120.4	C11—C10—H10	116.3
C4—C3—C2	121.89 (14)	C16—C11—C12	117.11 (14)
C4—C3—H3	119.1	C16—C11—C10	122.99 (14)
C2—C3—H3	119.1	C12—C11—C10	119.90 (14)
C5—C4—C3	118.66 (15)	C13—C12—C11	121.65 (17)
C5—C4—H4	120.7	C13—C12—Cl1	118.70 (14)
C3—C4—H4	120.7	C11—C12—Cl1	119.63 (12)
C4—C5—C6	121.20 (14)	C14—C13—C12	119.65 (18)
C4—C5—H5	119.4	C14—C13—H13	120.2
C6—C5—H5	119.4	C12—C13—H13	120.2
C5—C6—C1	118.97 (13)	C13—C14—C15	120.53 (17)
C5—C6—C7	120.44 (13)	C13—C14—H14	119.7
C1—C6—C7	120.58 (12)	C15—C14—H14	119.7
O1—C7—C6	124.58 (15)	C16—C15—C14	120.0 (2)
O1—C7—H7	117.7	C16—C15—H15	120.0
C6—C7—H7	117.7	C14—C15—H15	120.0
O2—C8—C9	107.51 (11)	C15—C16—C11	121.09 (18)
O2—C8—H8A	110.2	C15—C16—H16	119.5
C9—C8—H8A	110.2	C11—C16—H16	119.5
O2—C8—H8B	110.2	N1—C17—C9	178.10 (17)
C9—C8—H8B	110.2
C8—O2—C1—C2	−21.16 (19)	C17—C9—C10—C11	−177.54 (15)
C8—O2—C1—C6	160.05 (12)	C8—C9—C10—C11	0.5 (3)
O2—C1—C2—C3	−176.06 (14)	C9—C10—C11—C16	−37.5 (2)
C6—C1—C2—C3	2.7 (2)	C9—C10—C11—C12	143.27 (17)
C1—C2—C3—C4	−0.3 (3)	C16—C11—C12—C13	1.2 (2)
C2—C3—C4—C5	−1.7 (3)	C10—C11—C12—C13	−179.48 (15)
C3—C4—C5—C6	1.4 (3)	C16—C11—C12—Cl1	179.72 (12)
C4—C5—C6—C1	0.9 (2)	C10—C11—C12—Cl1	−1.0 (2)
C4—C5—C6—C7	−177.70 (15)	C11—C12—C13—C14	−0.4 (3)
O2—C1—C6—C5	175.89 (12)	Cl1—C12—C13—C14	−178.89 (14)
C2—C1—C6—C5	−2.9 (2)	C12—C13—C14—C15	−0.3 (3)
O2—C1—C6—C7	−5.54 (19)	C13—C14—C15—C16	0.2 (3)
C2—C1—C6—C7	175.62 (13)	C14—C15—C16—C11	0.7 (3)
C5—C6—C7—O1	0.0 (3)	C12—C11—C16—C15	−1.4 (2)
C1—C6—C7—O1	−178.53 (16)	C10—C11—C16—C15	179.34 (15)
C1—O2—C8—C9	−173.38 (11)	C10—C9—C17—N1	36 (6)
O2—C8—C9—C10	−149.36 (14)	C8—C9—C17—N1	−142 (6)
O2—C8—C9—C17	28.70 (17)