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

Govindan, S.; Vijayakumar, S.; Jayakumar, S.; Mannickam, B.; Sanmargam, A.

doi:10.1107/S1600536812003923

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o596

doi:10.1107/S1600536812003923

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

Suresh Govindan,^a Sabari Vijayakumar,^a Srinivasan Jayakumar,^b Bakthadoss Mannickam ^b and Aravindhan Sanmargam ^a ^*

^aDepartment of Physics, Presidency College, Chennai 600 005, India, and ^bDepartment of Organic Chemistry, University of Madras, Chennai 600 025, India
^*Correspondence e-mail: aravindhanpresidency@gmail.com

(Received 22 December 2011; accepted 30 January 2012; online 4 February 2012)

In the title compound, C₁₇H₁₄N₂O₂, the hydroxyethanimine group adopts an antiperiplanar conformation. In the crystal, molecules are linked by O—H⋯N hydrogen bonds, forming zigzag chains running along the c axis.

Related literature

For the structures of other acrylate derivatives, see: Zhang et al. (2009 ); Wang et al. (2011 ); SakthiMurugesan et al. (2011 ); Govindan et al. (2011 ). For the use of oxime ligands in coordination chemistry, see: Chaudhuri (2003 ). For the biological activity of caffeic acids, see: Hwang et al. (2001 ); Altug et al. (2008 ); Ates et al. (2006 ); Atik et al. (2006 ); Padinchare et al. (2001 ).

Experimental

Crystal data

C₁₇H₁₄N₂O₂
M_r = 278.30
Monoclinic, P 2₁ /c
a = 15.8867 (5) Å
b = 6.2381 (2) Å
c = 15.1874 (4) Å
β = 107.199 (2)°
V = 1437.81 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.2 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur-S diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.980, T_max = 0.990
19516 measured reflections
4490 independent reflections
2774 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.131
S = 0.99
4490 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N2ⁱ	0.82	2.10	2.9187 (17)	178
Symmetry code: (i) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812003923/bt5765sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003923/bt5765Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812003923/bt5765Isup3.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). Some naturally occurring caffeic acids and their esters attract much attention in biology and medicine (Hwang et al., 2001; Altug et al., 2008). These compounds show antiviral, antibacterial, vasoactive, antiatherogenic, antiproliferative, antioxidant and antiinflammatory properties (Atik et al., 2006; Padinchare et al., 2001; Ates et al., 2006). 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 and the results are presented here. X-Ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The oxime group has the C=N bond in an E configuration. The hydroxy ethanimine group is essentially coplanar with the ring to which it is attached. The crystal packing is stabilized by an O—H···N hydrogen bond(Fig. 2).

Related literature top

For the structures of other acrylate derivatives, see: Zhang et al. (2009); Wang et al. (2011); SakthiMurugesan et al. (2011); Govindan et al. (2011). For the use of oxime ligands in coordination chemistry, see: Chaudhuri (2003). For the biological activity of caffeic acids, see: Hwang et al. (2001); Altug et al. (2008); Ates et al. (2006); Atik et al. (2006); Padinchare et al. (2001).

Experimental top

To a stirred solution of (E)-2-((2-formylphenoxy)methyl)-3-phenylacrylonitrile (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 τimes 15 ml). The combined organic layer was washed with brine (2 τimes 10 ml) and dried over anhydrous Na2SO4 and then evaporated under reduced pressure to obtain (E)-2-((2-((E)-(Hydroxyimino)methyl)phenoxy)methyl)-3-phenylacrylonitrile as a colourless solid.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A view of the crystal packing. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

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

Crystal data top

C₁₇H₁₄N₂O₂	F(000) = 584
M_r = 278.30	D_x = 1.286 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8725 reflections
a = 15.8867 (5) Å	θ = 2.8–29.1°
b = 6.2381 (2) Å	µ = 0.09 mm⁻¹
c = 15.1874 (4) Å	T = 293 K
β = 107.199 (2)°	Monoclinic, colourless
V = 1437.81 (7) Å³	0.2 × 0.2 × 0.2 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur-S diffractometer	4490 independent reflections
Radiation source: fine-focus sealed tube	2774 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 15.9948 pixels mm^-1	θ_max = 31.4°, θ_min = 2.7°
ω scans	h = −20→23
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −9→9
T_min = 0.980, T_max = 0.990	l = −22→22
19516 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0521P)² + 0.226P] where P = (F_o² + 2F_c²)/3
4490 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₇H₁₄N₂O₂	V = 1437.81 (7) Å³
M_r = 278.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.8867 (5) Å	µ = 0.09 mm⁻¹
b = 6.2381 (2) Å	T = 293 K
c = 15.1874 (4) Å	0.2 × 0.2 × 0.2 mm
β = 107.199 (2)°

Data collection top

Oxford Diffraction Xcalibur-S diffractometer	4490 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2774 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.990	R_int = 0.031
19516 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 0.99	Δρ_max = 0.19 e Å⁻³
4490 reflections	Δρ_min = −0.21 e Å⁻³
191 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	0.30906 (9)	0.0194 (2)	0.29768 (9)	0.0471 (3)
H1	0.2662	0.0231	0.2407	0.057*
C2	0.37843 (8)	0.1812 (2)	0.31995 (8)	0.0405 (3)
C3	0.44575 (9)	0.1763 (2)	0.40269 (9)	0.0500 (3)
H3	0.4456	0.0697	0.4455	0.060*
C4	0.51256 (9)	0.3247 (2)	0.42297 (9)	0.0525 (3)
H4	0.5574	0.3176	0.4784	0.063*
C5	0.51234 (9)	0.4837 (2)	0.36050 (10)	0.0542 (4)
H5	0.5574	0.5849	0.3740	0.065*
C6	0.44610 (9)	0.4954 (2)	0.27781 (9)	0.0488 (3)
H6	0.4464	0.6041	0.2360	0.059*
C7	0.37943 (8)	0.3449 (2)	0.25758 (8)	0.0399 (3)
C8	0.30879 (9)	0.5024 (2)	0.11052 (9)	0.0474 (3)
H8A	0.3612	0.4952	0.0904	0.057*
H8B	0.3058	0.6435	0.1363	0.057*
C9	0.22813 (8)	0.4609 (2)	0.03129 (8)	0.0411 (3)
C10	0.22894 (9)	0.2607 (2)	−0.01427 (9)	0.0486 (3)
C11	0.16197 (9)	0.6014 (2)	0.00727 (8)	0.0444 (3)
H11	0.1718	0.7251	0.0431	0.053*
C12	0.07740 (9)	0.5990 (2)	−0.06398 (8)	0.0435 (3)
C13	0.04331 (10)	0.4260 (2)	−0.12169 (10)	0.0577 (4)
H13	0.0768	0.3021	−0.1177	0.069*
C14	−0.03912 (10)	0.4363 (3)	−0.18424 (10)	0.0629 (4)
H14	−0.0607	0.3196	−0.2223	0.075*
C15	−0.08983 (10)	0.6164 (3)	−0.19123 (11)	0.0633 (4)
H15	−0.1460	0.6212	−0.2330	0.076*
C16	−0.05728 (11)	0.7892 (3)	−0.13634 (12)	0.0694 (5)
H16	−0.0911	0.9128	−0.1414	0.083*
C17	0.02527 (10)	0.7807 (2)	−0.07360 (10)	0.0577 (4)
H17	0.0466	0.8996	−0.0368	0.069*
N1	0.30657 (8)	−0.12586 (19)	0.35497 (8)	0.0527 (3)
N2	0.23413 (9)	0.0992 (2)	−0.04726 (10)	0.0728 (4)
O1	0.23639 (8)	−0.26430 (19)	0.31926 (8)	0.0716 (3)
H1A	0.2369	−0.3587	0.3570	0.107*
O2	0.31108 (6)	0.34087 (15)	0.17729 (6)	0.0487 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0432 (7)	0.0502 (8)	0.0433 (7)	0.0001 (6)	0.0055 (6)	0.0077 (6)
C2	0.0369 (6)	0.0437 (7)	0.0396 (6)	0.0029 (5)	0.0093 (5)	0.0023 (5)
C3	0.0488 (8)	0.0581 (8)	0.0397 (7)	0.0044 (7)	0.0079 (6)	0.0084 (6)
C4	0.0455 (8)	0.0654 (9)	0.0387 (7)	0.0008 (7)	0.0004 (6)	−0.0043 (6)
C5	0.0488 (8)	0.0567 (9)	0.0514 (8)	−0.0101 (7)	0.0061 (6)	−0.0076 (7)
C6	0.0479 (8)	0.0474 (8)	0.0470 (7)	−0.0046 (6)	0.0075 (6)	0.0040 (6)
C7	0.0359 (6)	0.0441 (7)	0.0372 (6)	0.0032 (5)	0.0070 (5)	0.0013 (5)
C8	0.0481 (8)	0.0434 (7)	0.0456 (7)	−0.0020 (6)	0.0060 (6)	0.0092 (6)
C9	0.0460 (7)	0.0386 (6)	0.0367 (6)	−0.0009 (5)	0.0090 (5)	0.0048 (5)
C10	0.0443 (8)	0.0476 (8)	0.0497 (7)	0.0045 (6)	0.0076 (6)	0.0034 (6)
C11	0.0524 (8)	0.0397 (7)	0.0387 (6)	0.0005 (6)	0.0096 (6)	−0.0009 (5)
C12	0.0453 (7)	0.0462 (7)	0.0377 (6)	0.0033 (6)	0.0104 (5)	0.0028 (5)
C13	0.0551 (9)	0.0542 (9)	0.0547 (8)	0.0079 (7)	0.0023 (7)	−0.0070 (7)
C14	0.0565 (10)	0.0695 (10)	0.0541 (9)	−0.0032 (8)	0.0030 (7)	−0.0095 (7)
C15	0.0449 (8)	0.0833 (12)	0.0551 (9)	0.0031 (8)	0.0048 (7)	0.0054 (8)
C16	0.0536 (10)	0.0700 (11)	0.0773 (11)	0.0192 (8)	0.0080 (8)	0.0012 (9)
C17	0.0551 (9)	0.0527 (9)	0.0602 (9)	0.0091 (7)	0.0093 (7)	−0.0048 (7)
N1	0.0521 (7)	0.0517 (7)	0.0522 (7)	−0.0081 (5)	0.0119 (5)	0.0032 (5)
N2	0.0731 (10)	0.0553 (8)	0.0837 (10)	0.0116 (7)	0.0136 (8)	−0.0131 (7)
O1	0.0701 (8)	0.0631 (7)	0.0727 (7)	−0.0239 (6)	0.0074 (6)	0.0106 (6)
O2	0.0427 (5)	0.0525 (5)	0.0421 (5)	−0.0062 (4)	−0.0009 (4)	0.0133 (4)

Geometric parameters (Å, º) top

C1—N1	1.2649 (16)	C9—C11	1.3339 (18)
C1—C2	1.4583 (18)	C9—C10	1.4296 (19)
C1—H1	0.9300	C10—N2	1.1392 (17)
C2—C3	1.3889 (18)	C11—C12	1.4548 (18)
C2—C7	1.3962 (17)	C11—H11	0.9300
C3—C4	1.373 (2)	C12—C17	1.3857 (19)
C3—H3	0.9300	C12—C13	1.3951 (19)
C4—C5	1.372 (2)	C13—C14	1.373 (2)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.3814 (19)	C14—C15	1.368 (2)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.3804 (18)	C15—C16	1.367 (2)
C6—H6	0.9300	C15—H15	0.9300
C7—O2	1.3725 (14)	C16—C17	1.375 (2)
C8—O2	1.4225 (14)	C16—H16	0.9300
C8—C9	1.4983 (18)	C17—H17	0.9300
C8—H8A	0.9700	N1—O1	1.3876 (15)
C8—H8B	0.9700	O1—H1A	0.8200

N1—C1—C2	120.76 (12)	C11—C9—C8	121.58 (12)
N1—C1—H1	119.6	C10—C9—C8	114.31 (11)
C2—C1—H1	119.6	N2—C10—C9	176.18 (16)
C3—C2—C7	118.02 (12)	C9—C11—C12	132.56 (12)
C3—C2—C1	121.43 (12)	C9—C11—H11	113.7
C7—C2—C1	120.55 (11)	C12—C11—H11	113.7
C4—C3—C2	121.70 (13)	C17—C12—C13	117.24 (13)
C4—C3—H3	119.2	C17—C12—C11	117.49 (12)
C2—C3—H3	119.2	C13—C12—C11	125.23 (12)
C5—C4—C3	119.26 (12)	C14—C13—C12	120.79 (14)
C5—C4—H4	120.4	C14—C13—H13	119.6
C3—C4—H4	120.4	C12—C13—H13	119.6
C4—C5—C6	120.82 (13)	C15—C14—C13	120.76 (15)
C4—C5—H5	119.6	C15—C14—H14	119.6
C6—C5—H5	119.6	C13—C14—H14	119.6
C7—C6—C5	119.64 (12)	C16—C15—C14	119.48 (14)
C7—C6—H6	120.2	C16—C15—H15	120.3
C5—C6—H6	120.2	C14—C15—H15	120.3
O2—C7—C6	124.30 (11)	C15—C16—C17	120.22 (15)
O2—C7—C2	115.14 (11)	C15—C16—H16	119.9
C6—C7—C2	120.56 (11)	C17—C16—H16	119.9
O2—C8—C9	106.60 (10)	C16—C17—C12	121.48 (15)
O2—C8—H8A	110.4	C16—C17—H17	119.3
C9—C8—H8A	110.4	C12—C17—H17	119.3
O2—C8—H8B	110.4	C1—N1—O1	111.22 (11)
C9—C8—H8B	110.4	N1—O1—H1A	109.5
H8A—C8—H8B	108.6	C7—O2—C8	117.86 (9)
C11—C9—C10	124.11 (12)

N1—C1—C2—C3	2.7 (2)	C8—C9—C11—C12	−178.61 (12)
N1—C1—C2—C7	−178.10 (13)	C9—C11—C12—C17	−176.32 (13)
C7—C2—C3—C4	−1.05 (19)	C9—C11—C12—C13	5.7 (2)
C1—C2—C3—C4	178.19 (12)	C17—C12—C13—C14	−0.9 (2)
C2—C3—C4—C5	0.8 (2)	C11—C12—C13—C14	177.09 (14)
C3—C4—C5—C6	−0.2 (2)	C12—C13—C14—C15	−0.2 (2)
C4—C5—C6—C7	−0.2 (2)	C13—C14—C15—C16	1.1 (3)
C5—C6—C7—O2	−179.43 (12)	C14—C15—C16—C17	−1.0 (3)
C5—C6—C7—C2	0.0 (2)	C15—C16—C17—C12	−0.1 (3)
C3—C2—C7—O2	−179.90 (11)	C13—C12—C17—C16	1.1 (2)
C1—C2—C7—O2	0.86 (16)	C11—C12—C17—C16	−177.09 (14)
C3—C2—C7—C6	0.63 (18)	C2—C1—N1—O1	−178.97 (12)
C1—C2—C7—C6	−178.62 (12)	C6—C7—O2—C8	0.00 (18)
O2—C8—C9—C11	116.39 (13)	C2—C7—O2—C8	−179.45 (11)
O2—C8—C9—C10	−63.22 (14)	C9—C8—O2—C7	−179.66 (10)
C10—C9—C11—C12	1.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2ⁱ	0.82	2.10	2.9187 (17)	178

Symmetry code: (i) x, −y−1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄N₂O₂
M_r	278.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.8867 (5), 6.2381 (2), 15.1874 (4)
β (°)	107.199 (2)
V (Å³)	1437.81 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.2 × 0.2 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur-S diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.980, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	19516, 4490, 2774
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.733

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.131, 0.99
No. of reflections	4490
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.21

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2ⁱ	0.82	2.10	2.9187 (17)	178.3

Symmetry code: (i) x, −y−1/2, z+1/2.

Acknowledgements

AS thanks the UGC, India, for financial support.

References

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Volume 68| Part 3| March 2012| Page o596

doi:10.1107/S1600536812003923

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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-phenyl­acrylo­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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