(E)-2-({2-[(E)-(Hy­droxy­imino)­meth­yl]phen­oxy}meth­yl)-3-o-tolyl­acrylonitrile

Govindan, E.; Srinivasan, J.; Bakthadoss, M.; SubbiahPandi, A.

doi:10.1107/S1600536812001481

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o484

doi:10.1107/S1600536812001481

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(E)-2-({2-[(E)-(Hydroxyimino)methyl]phenoxy}methyl)-3-o-tolylacrylonitrile

E. Govindan,^a J. Srinivasan,^b M. Bakthadoss ^b and A. SubbiahPandi ^a ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: a_sp59@yahoo.in

(Received 5 January 2012; accepted 12 January 2012; online 21 January 2012)

In the title compound, C₁₈H₁₆N₂O₂, the dihedral angle between the mean planes through the two benzene rings is 56.8 (6)°. The enoate group assumes an extended conformation. The hydroxyethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane being 0.047 (1) Å for the hydroxyimino O atom. In the crystal, the molecules are linked into cyclic centrosymmetric dimers with R₂²(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_r = 292.33
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.050
wR(F²) = 0.163
S = 1.06
5557 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) -x-1, -y, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812001481/qm2049sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812001481/qm2049Isup3.cml

checkCIF report

Comment top

Recently, 2-cyanoacrylates have been extensively used as agrochemicals because of their unique mechanism of action and good environmental profiles (Zhang et al., 2009). Oximes are a classical type of chelating ligands which are widely used in coordination and analytical chemistry (Chaudhuri, 2003). Against this background, and in order to obtain detailed information on molecular conformations in the solid state, an X-ray study of the title compound was carried out.

X-Ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The bond lengths and angles in (Fig. 1) agree with those observed in other tolylacrylonitile derivatives (Govindan et al., 2011). The whole molecule is not planar as the dihedral angle between the two phenyl rings is 56.8 (6)°, The oxime group having the C=N forming an E configuration. The hydroxyethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane of the hydroxyethanimine [C=N—OH] group is 0.047 (1) Å. for the O1 atom.

The enoate group assumes an extended conformation as can be seen from torsion angles C2—C1—N1—O1 [177.9 (2)°] and C1—C2—C3—C4 [-177.1 (2) °]. The atom C15 in the molecule (x,y,z) donate one proton to atom O1 of the molecule at (-1 - x,-y,1 - z) forming a C(6) chain along b axis. The hydroxyethanimine group in the molecules are linked into cyclic centrosymmetric dimers via O—H···N hydrogen bonds with the motif R²₂(6) (Fig. 2). In addition to van der Waals interaction, the crystal packing is stabilized by C—H···O interactions.

Related literature top

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 top

To a stirred solution of (E)-2-((2-formylphenoxy)methyl)-3-o- tolylacrylonitrile (4 mmol) in 10 ml of EtOH/H₂O mixture (1:1) was added NH₂OH.HCl (6 mmol) in the presence of 50% NaOH at room temperature. Then the reaction mixture was allowed to stir at room temperature for 1.5 h. After completion of the reaction, solvent was removed and the crude mass was diluted with water (15 ml) and extracted with ethyl acetate (3 x 15 ml). The combined organic layer was washed with brine (2 x 10 ml) and dried over anhydrous Na₂SO₄ and then evaporated under reduced pressure to obtain (2E)-2-((2-((Hydroxyimino)methyl) phenoxy)methyl)-3-o-tolylacrylonitrile as a colourless solid.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title molecule with the atom labelling scheme. The displacement ellipsoids are drawn at the 30% probability level while the H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The crystal structure showing the centrosymmetric hydrogen bond motif R₂²(6). For the sake of clarity, the H atoms not involved in the motif have been omitted. The atoms marked with an asterisk (*) are at the symmetry position (-1 - x, -y, 1 - z). The dashed lines indicate the hydrogen bonds.

(E)-2-({2-[(E)-(Hydroxyimino)methyl]phenoxy}methyl)- 3-o-tolylacrylonitrile top

Crystal data top

C₁₈H₁₆N₂O₂	Z = 2
M_r = 292.33	F(000) = 308
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0845P)² + 0.0621P] where P = (F_o² + 2F_c²)/3
5557 reflections	(Δ/σ)_max < 0.001
201 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₈H₁₆N₂O₂	γ = 99.642 (1)°
M_r = 292.33	V = 778.32 (4) Å³
Triclinic, P1	Z = 2
a = 7.0214 (2) Å	Mo Kα radiation
b = 10.5094 (3) Å	µ = 0.08 mm⁻¹
c = 10.8854 (3) Å	T = 293 K
α = 97.636 (1)°	0.25 × 0.22 × 0.19 mm
β = 95.953 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5557 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3825 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.983	R_int = 0.029
21189 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.06	Δρ_max = 0.26 e Å⁻³
5557 reflections	Δρ_min = −0.19 e Å⁻³
201 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x−1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₂O₂
M_r	292.33
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.0214 (2), 10.5094 (3), 10.8854 (3)
α, β, γ (°)	97.636 (1), 95.953 (1), 99.642 (1)
V (Å³)	778.32 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.22 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.978, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	21189, 5557, 3825
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.798

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.163, 1.06
No. of reflections	5557
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.19

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1ⁱ	0.82	2.07	2.7962 (13)	146.7

Symmetry code: (i) −x−1, −y, −z+1.

Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison Wisconsin, USA. Google Scholar
Chaudhuri, P. (2003). Coord. Chem. Rev. 243, 143–168. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Govindan, E., SakthiMurugesan, K., Srinivasan, J., Bakthadoss, M. & SubbiahPandi, A. (2011). Acta Cryst. E67, o2753. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, D., Zhang, X. & Guo, L. (2009). Acta Cryst. E65, o90. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 2| February 2012| Page o484

doi:10.1107/S1600536812001481

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-2-({2-[(E)-(Hy­dr­oxy­imino)­meth­yl]phen­­oxy}meth­yl)-3-o-tolyl­acrylo­nitrile

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-2-({2-[(E)-(Hydroxyimino)methyl]phenoxy}methyl)-3-o-tolylacrylonitrile