(E)-2-({2-[(E)-(Hy-droxy-imino)-meth-yl]phen-oxy}meth-yl)-3-o-tolyl-acrylonitrile.

In the title compound, C(18)H(16)N(2)O(2), the dihedral angle between the mean planes through the two benzene rings is 56.8 (6)°. The enoate group assumes an extended conformation. The hy-droxy-ethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane being 0.047 (1) Å for the hy-droxy-imino O atom. In the crystal, the mol-ecules are linked into cyclic centrosymmetric dimers with R(2) (2)(6) motifs via O-H⋯N hydrogen bonds.

Related literature

For the use of 2-cyano­acrylates and oximes as agrochemicals, see: Zhang et al. (2009 ▶). For the use of oximes as chelating ligands in coordination and analytical chemistry, see: Chaudhuri et al. (2003 ▶). For a related structure, see: Govindan et al. (2011 ▶).

Experimental

Crystal data

C18H16N2O2

M = 292.33

Triclinic,

a = 7.0214 (2) Å

b = 10.5094 (3) Å

c = 10.8854 (3) Å

α = 97.636 (1)°

β = 95.953 (1)°

γ = 99.642 (1)°

V = 778.32 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.978, T max = 0.983

21189 measured reflections

5557 independent reflections

3825 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.163

S = 1.06

5557 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.19 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 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812001481/qm2049sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001481/qm2049Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001481/qm2049Isup3.cml

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

C18H16N2O2	Z = 2
Mr = 292.33	F(000) = 308
Triclinic, P1	Dx = 1.247 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0214 (2) Å	Cell parameters from 5557 reflections
b = 10.5094 (3) Å	θ = 1.9°
c = 10.8854 (3) Å	µ = 0.08 mm−1
α = 97.636 (1)°	T = 293 K
β = 95.953 (1)°	Block, white crystalline
γ = 99.642 (1)°	0.25 × 0.22 × 0.19 mm
V = 778.32 (4) Å3

Bruker APEXII CCD area-detector diffractometer	5557 independent reflections
Radiation source: fine-focus sealed tube	3825 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω and φ scans	θmax = 34.6°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→11
Tmin = 0.978, Tmax = 0.983	k = −16→15
21189 measured reflections	l = −16→16

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0845P)2 + 0.0621P] where P = (Fo2 + 2Fc2)/3
5557 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.18 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	−0.15593 (16)	0.00826 (11)	0.65422 (11)	0.0458 (3)
H1	−0.1182	0.0760	0.7210	0.055*
C2	−0.02936 (15)	−0.08709 (10)	0.63051 (10)	0.0403 (2)
C3	−0.08597 (19)	−0.20010 (12)	0.54286 (12)	0.0537 (3)
H3	−0.2068	−0.2148	0.4943	0.064*
C4	0.0343 (2)	−0.29046 (12)	0.52696 (13)	0.0590 (3)
H4	−0.0051	−0.3649	0.4674	0.071*
C5	0.21237 (19)	−0.27051 (12)	0.59921 (12)	0.0536 (3)
H5	0.2919	−0.3327	0.5897	0.064*
C6	0.27362 (17)	−0.15902 (11)	0.68554 (11)	0.0465 (3)
H6	0.3947	−0.1455	0.7337	0.056*
C7	0.15422 (14)	−0.06683 (10)	0.70047 (9)	0.0381 (2)
C8	0.34958 (15)	0.05707 (11)	0.88418 (10)	0.0430 (2)
H8A	0.4795	0.0729	0.8598	0.052*
H8B	0.3317	−0.0240	0.9187	0.052*
C9	0.32336 (14)	0.16826 (10)	0.97920 (10)	0.0387 (2)
C10	0.12321 (15)	0.17173 (11)	0.99392 (11)	0.0467 (3)
C11	0.47398 (14)	0.25582 (10)	1.04165 (10)	0.0395 (2)
H11	0.5958	0.2450	1.0203	0.047*
C12	0.47398 (15)	0.36647 (10)	1.13905 (10)	0.0399 (2)
C13	0.3269 (2)	0.36659 (13)	1.21596 (12)	0.0552 (3)
H13	0.2299	0.2930	1.2087	0.066*
C14	0.3234 (2)	0.47427 (15)	1.30267 (15)	0.0735 (4)
H14	0.2238	0.4735	1.3527	0.088*
C15	0.4678 (3)	0.58260 (15)	1.31470 (16)	0.0760 (5)
H15	0.4642	0.6563	1.3714	0.091*
C16	0.6170 (2)	0.58189 (12)	1.24310 (14)	0.0609 (3)
H16	0.7149	0.6554	1.2533	0.073*
C17	0.62672 (16)	0.47510 (11)	1.15593 (11)	0.0441 (2)
C18	0.79547 (18)	0.47851 (14)	1.08190 (15)	0.0597 (3)
H18A	0.8811	0.5616	1.1046	0.090*
H18B	0.7484	0.4657	0.9943	0.090*
H18C	0.8651	0.4104	1.0993	0.090*
N1	−0.31578 (13)	0.00044 (10)	0.58572 (9)	0.0461 (2)
N2	−0.03874 (16)	0.17076 (12)	0.99832 (14)	0.0698 (4)
O1	−0.41663 (12)	0.09866 (9)	0.62794 (9)	0.0605 (3)
H1A	−0.5163	0.0935	0.5797	0.091*
O2	0.20712 (11)	0.04926 (7)	0.77921 (7)	0.0467 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0381 (5)	0.0484 (6)	0.0469 (6)	0.0088 (4)	−0.0016 (4)	−0.0025 (5)
C2	0.0366 (5)	0.0415 (5)	0.0403 (5)	0.0061 (4)	0.0010 (4)	0.0014 (4)
C3	0.0508 (6)	0.0495 (6)	0.0520 (7)	0.0048 (5)	−0.0073 (5)	−0.0076 (5)
C4	0.0703 (8)	0.0439 (6)	0.0553 (7)	0.0082 (6)	0.0010 (6)	−0.0108 (5)
C5	0.0648 (7)	0.0449 (6)	0.0527 (7)	0.0205 (5)	0.0097 (6)	−0.0010 (5)
C6	0.0455 (6)	0.0466 (6)	0.0471 (6)	0.0159 (5)	0.0017 (4)	0.0005 (5)
C7	0.0387 (5)	0.0371 (5)	0.0368 (5)	0.0077 (4)	0.0022 (4)	0.0004 (4)
C8	0.0359 (5)	0.0443 (5)	0.0456 (6)	0.0138 (4)	−0.0041 (4)	−0.0056 (4)
C9	0.0350 (4)	0.0378 (5)	0.0422 (5)	0.0098 (4)	0.0021 (4)	−0.0002 (4)
C10	0.0386 (5)	0.0400 (5)	0.0571 (7)	0.0063 (4)	0.0048 (5)	−0.0061 (5)
C11	0.0360 (5)	0.0395 (5)	0.0415 (5)	0.0082 (4)	0.0023 (4)	0.0015 (4)
C12	0.0402 (5)	0.0369 (5)	0.0403 (5)	0.0070 (4)	0.0004 (4)	0.0008 (4)
C13	0.0579 (7)	0.0501 (6)	0.0516 (7)	−0.0010 (5)	0.0152 (5)	−0.0060 (5)
C14	0.0811 (10)	0.0672 (9)	0.0675 (9)	0.0059 (7)	0.0313 (8)	−0.0141 (7)
C15	0.0977 (12)	0.0526 (8)	0.0692 (9)	0.0061 (7)	0.0200 (8)	−0.0191 (7)
C16	0.0689 (8)	0.0408 (6)	0.0638 (8)	−0.0020 (6)	0.0026 (6)	−0.0049 (5)
C17	0.0426 (5)	0.0390 (5)	0.0477 (6)	0.0057 (4)	−0.0020 (4)	0.0043 (4)
C18	0.0435 (6)	0.0541 (7)	0.0775 (9)	−0.0001 (5)	0.0086 (6)	0.0063 (6)
N1	0.0370 (4)	0.0491 (5)	0.0508 (5)	0.0111 (4)	0.0010 (4)	0.0023 (4)
N2	0.0416 (5)	0.0669 (7)	0.0954 (9)	0.0107 (5)	0.0122 (5)	−0.0110 (6)
O1	0.0460 (5)	0.0644 (6)	0.0689 (6)	0.0224 (4)	−0.0026 (4)	−0.0054 (4)
O2	0.0442 (4)	0.0416 (4)	0.0490 (4)	0.0146 (3)	−0.0114 (3)	−0.0076 (3)

C1—N1	1.2655 (14)	C10—N2	1.1415 (15)
C1—C2	1.4621 (14)	C11—C12	1.4658 (13)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.3932 (15)	C12—C13	1.3950 (16)
C2—C7	1.3958 (14)	C12—C17	1.4074 (16)
C3—C4	1.3783 (18)	C13—C14	1.3793 (17)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.3751 (19)	C14—C15	1.374 (2)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.3768 (16)	C15—C16	1.369 (2)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.3880 (14)	C16—C17	1.3859 (16)
C6—H6	0.9300	C16—H16	0.9300
C7—O2	1.3658 (12)	C17—C18	1.4987 (17)
C8—O2	1.4225 (12)	C18—H18A	0.9600
C8—C9	1.5032 (13)	C18—H18B	0.9600
C8—H8A	0.9700	C18—H18C	0.9600
C8—H8B	0.9700	N1—O1	1.4016 (12)
C9—C11	1.3364 (14)	O1—H1A	0.8200
C9—C10	1.4367 (14)
N1—C1—C2	121.33 (10)	C9—C11—C12	129.04 (9)
N1—C1—H1	119.3	C9—C11—H11	115.5
C2—C1—H1	119.3	C12—C11—H11	115.5
C3—C2—C7	118.07 (10)	C13—C12—C17	119.11 (10)
C3—C2—C1	122.78 (10)	C13—C12—C11	121.69 (10)
C7—C2—C1	119.13 (9)	C17—C12—C11	119.20 (10)
C4—C3—C2	121.07 (11)	C14—C13—C12	120.96 (12)
C4—C3—H3	119.5	C14—C13—H13	119.5
C2—C3—H3	119.5	C12—C13—H13	119.5
C5—C4—C3	119.99 (11)	C15—C14—C13	119.68 (13)
C5—C4—H4	120.0	C15—C14—H14	120.2
C3—C4—H4	120.0	C13—C14—H14	120.2
C4—C5—C6	120.34 (11)	C16—C15—C14	119.93 (12)
C4—C5—H5	119.8	C16—C15—H15	120.0
C6—C5—H5	119.8	C14—C15—H15	120.0
C5—C6—C7	119.82 (11)	C15—C16—C17	122.09 (12)
C5—C6—H6	120.1	C15—C16—H16	119.0
C7—C6—H6	120.1	C17—C16—H16	119.0
O2—C7—C6	123.73 (9)	C16—C17—C12	118.08 (11)
O2—C7—C2	115.58 (8)	C16—C17—C18	119.87 (11)
C6—C7—C2	120.66 (10)	C12—C17—C18	122.04 (10)
O2—C8—C9	107.03 (8)	C17—C18—H18A	109.5
O2—C8—H8A	110.3	C17—C18—H18B	109.5
C9—C8—H8A	110.3	H18A—C18—H18B	109.5
O2—C8—H8B	110.3	C17—C18—H18C	109.5
C9—C8—H8B	110.3	H18A—C18—H18C	109.5
H8A—C8—H8B	108.6	H18B—C18—H18C	109.5
C11—C9—C10	124.04 (9)	C1—N1—O1	111.76 (9)
C11—C9—C8	122.27 (9)	N1—O1—H1A	109.5
C10—C9—C8	113.68 (9)	C7—O2—C8	118.07 (8)
N2—C10—C9	175.85 (13)
N1—C1—C2—C3	−8.33 (19)	C8—C9—C11—C12	−177.93 (10)
N1—C1—C2—C7	173.47 (11)	C9—C11—C12—C13	26.68 (19)
C7—C2—C3—C4	1.03 (19)	C9—C11—C12—C17	−153.67 (12)
C1—C2—C3—C4	−177.18 (13)	C17—C12—C13—C14	3.8 (2)
C2—C3—C4—C5	0.8 (2)	C11—C12—C13—C14	−176.50 (13)
C3—C4—C5—C6	−1.6 (2)	C12—C13—C14—C15	−0.7 (3)
C4—C5—C6—C7	0.57 (19)	C13—C14—C15—C16	−1.8 (3)
C5—C6—C7—O2	−176.62 (11)	C14—C15—C16—C17	1.1 (3)
C5—C6—C7—C2	1.26 (18)	C15—C16—C17—C12	2.0 (2)
C3—C2—C7—O2	176.01 (10)	C15—C16—C17—C18	−178.74 (15)
C1—C2—C7—O2	−5.71 (15)	C13—C12—C17—C16	−4.40 (18)
C3—C2—C7—C6	−2.03 (17)	C11—C12—C17—C16	175.94 (11)
C1—C2—C7—C6	176.25 (10)	C13—C12—C17—C18	176.37 (12)
O2—C8—C9—C11	−135.77 (11)	C11—C12—C17—C18	−3.29 (17)
O2—C8—C9—C10	43.22 (13)	C2—C1—N1—O1	177.80 (10)
C11—C9—C10—N2	151.8 (19)	C6—C7—O2—C8	−25.64 (15)
C8—C9—C10—N2	−27 (2)	C2—C7—O2—C8	156.39 (10)
C10—C9—C11—C12	3.19 (19)	C9—C8—O2—C7	−157.61 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1i	0.82	2.07	2.7962 (13)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1i	0.82	2.07	2.7962 (13)	147

Symmetry code: (i) .