Methyl (E)-2-({2-[(E)-(hy­droxy­imino)­meth­yl]phen­oxy}meth­yl)-3-(4-methyl­phen­yl)acrylate

doi:10.1107/S1600536812019046

Acta Crystallogr Sect E Struct Rep Online. 2012 June 1; 68(Pt 6): o1617.

Published online 2012 May 5. doi: 10.1107/S1600536812019046

PMCID: PMC3379223

Methyl (E)-2-({2-[(E)-(hydroxyimino)methyl]phenoxy}methyl)-3-(4-methylphenyl)acrylate

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

^aDepartment of Physics, S.M.K. Fomra Institute of Technology, Thaiyur, Chennai 603 103, India

^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India

^cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India

Correspondence e-mail: a_sp59/at/yahoo.in

Received April 20, 2012; Accepted April 27, 2012.

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Abstract

In the title compound, C₁₉H₁₉NO₄, the dihedral angle between the mean planes through the benzene rings is 82.18 (7)°. The C=N double bond is trans-configured. The molecules are linked into centrosymmetric dimers via pairs of O—H (...)

N hydrogen bonds with the motif R ₂ ²(6). The crystal packing also features C—H (...)

O interactions. The methyl group attached to one of the aromatic rings is disordered over two almost equally occupied positions [occpancy ratio = 0.51 (4):0.49 (4)].

Related literature

For information on oximes, see: Chaudhuri (2003

). For a related structure, see: SakthiMurugesan et al. (2011

An external file that holds a picture, illustration, etc.
Object name is e-68-o1617-scheme1.jpg Object name is e-68-o1617-scheme1.jpg

Experimental

Crystal data

C₁₉H₁₉NO₄
M _r = 325.35
Triclinic,
a = 8.8683 (2) Å
b = 9.3246 (2) Å
c = 11.9259 (3) Å
α = 75.200 (2)°
β = 76.453 (2)°
γ = 65.142 (1)°
V = 856.04 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T _min = 0.970, T _max = 0.978
20292 measured reflections
4580 independent reflections
3493 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.132
S = 1.04
4580 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.20 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: PLATON (Spek, 2009

); software used to prepare material for publication: SHELXL97 and PLATON.

Table 1

Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019046/bt5884sup1.cif

Click here to view.^{(20K, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019046/bt5884Isup2.hkl

Click here to view.^{(224K, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812019046/bt5884Isup3.cml

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

Acknowledgments

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

supplementary crystallographic information

Comment

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 acrylate derivatives (SakthiMurugesan et al., 2011). the whole molecule is not planar as the dihedral angle between the two phenyl rings is 82.18 (7)°, it shows that both the rings are almost perpendicular to each other. The methoxybutene group connects the two phenyl rings, results in twisting the rings and placed those rings in perpendicular direction. The oxime group having the C═N forming an E configuration. The atom C19 is deviated by -0.037 (2) Å from the least squares plane of the C13—C18 ring. The hydroxyethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane being -0.008 (1) Å for the C2 atom.

The enoate group assumes an extended conformation as can be seen from torsion angles C8—C9—C10—O3 [169.97 (15)°] and C9—C10—O4—C11 [179.55 (14)°]. The hydroxyethanimine group in the molecules are linked into cyclic centrosymmetric dimers via O—H···N hydrogen bonds with the motif R₂²(6). In addition to van der Waals interactions the crystal packing is stabilized by C–H..O and O–H···N interactions.

Experimental

To a stirred solution of (E)-methyl 2-((2-formylphenoxy)methyl)-3 - p-tolyacrylate (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 crude mass was diluted with water (15 ml) and extracted with ethyl acetate (3x15ml). The combined organic layer was washed with brine (2x10ml) and dried over anhydrous Na₂SO₄ and then evaporated under reduced pressure to obtain(E)-methyl 2-((2-((E)-(hydroxyimino) methyl)phenoxy) methyl)-3-p-tolylacrylate as a colourless solid. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in acetone at room temperature.

Figures

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 (2 - x, -y, 1 - z). The (more ...)

Crystal data

C₁₉H₁₉NO₄	Z = 2
M_r = 325.35	F(000) = 344
Triclinic, P1	D_x = 1.262 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8683 (2) Å	Cell parameters from 6056 reflections
b = 9.3246 (2) Å	θ = 2.5–32.5°
c = 11.9259 (3) Å	µ = 0.09 mm⁻¹
α = 75.200 (2)°	T = 293 K
β = 76.453 (2)°	Block, white crystalline
γ = 65.142 (1)°	0.35 × 0.30 × 0.25 mm
V = 856.04 (3) Å³

Data collection

Bruker APEXII CCD area-detector diffractometer	4580 independent reflections
Radiation source: fine-focus sealed tube	3493 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω and scans	θ_max = 29.2°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.970, T_max = 0.978	k = −12→12
20292 measured reflections	l = −16→16

Refinement

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0596P)² + 0.1563P] where P = (F_o² + 2F_c²)/3
4580 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Special details

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)

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.30137 (15)	0.78709 (15)	0.40342 (11)	0.0446 (3)
H1	0.3839	0.8244	0.3607	0.053*
C2	0.32860 (14)	0.61892 (14)	0.41323 (10)	0.0397 (3)
C3	0.24555 (17)	0.54149 (16)	0.50493 (12)	0.0521 (3)
H3	0.1701	0.5977	0.5623	0.063*
C4	0.2729 (2)	0.38274 (18)	0.51246 (13)	0.0608 (4)
H4	0.2161	0.3325	0.5743	0.073*
C5	0.38495 (19)	0.29887 (16)	0.42785 (13)	0.0569 (3)
H5	0.4027	0.1920	0.4326	0.068*
C6	0.47131 (16)	0.37155 (15)	0.33607 (12)	0.0476 (3)
H6	0.5470	0.3139	0.2795	0.057*
C7	0.44431 (14)	0.53102 (13)	0.32886 (10)	0.0385 (2)
C8	0.64247 (16)	0.53394 (14)	0.15207 (11)	0.0450 (3)
H8A	0.5849	0.5135	0.1017	0.054*
H8B	0.7225	0.4320	0.1859	0.054*
C9	0.73103 (15)	0.64103 (15)	0.08311 (11)	0.0441 (3)
C10	0.89857 (17)	0.60977 (17)	0.11066 (13)	0.0532 (3)
C11	1.0978 (2)	0.4600 (3)	0.24022 (17)	0.0852 (6)
H11A	1.1801	0.4565	0.1713	0.128*
H11B	1.1307	0.3571	0.2908	0.128*
H11C	1.0899	0.5402	0.2807	0.128*
C12	0.67354 (16)	0.76491 (15)	−0.00294 (11)	0.0475 (3)
H12	0.7450	0.8193	−0.0359	0.057*
C13	0.51907 (16)	0.82972 (14)	−0.05413 (11)	0.0456 (3)
C14	0.37187 (17)	0.80613 (17)	−0.00162 (12)	0.0546 (3)
H14	0.3663	0.7467	0.0737	0.065*
C15	0.23412 (19)	0.86949 (18)	−0.05950 (14)	0.0594 (4)
H15	0.1378	0.8506	−0.0228	0.071*
C16	0.23571 (19)	0.96063 (17)	−0.17098 (13)	0.0578 (4)
C17	0.3798 (2)	0.98842 (18)	−0.22200 (13)	0.0619 (4)
H17	0.3833	1.0512	−0.2962	0.074*
C18	0.51779 (19)	0.92530 (16)	−0.16541 (12)	0.0558 (3)
H18	0.6129	0.9466	−0.2020	0.067*
C19	0.0852 (3)	1.0257 (3)	−0.23393 (18)	0.0884 (6)
H19A	0.0030	0.9840	−0.1886	0.133*	0.51 (4)
H19B	0.1192	0.9937	−0.3093	0.133*	0.51 (4)
H19C	0.0376	1.1408	−0.2440	0.133*	0.51 (4)
H19D	0.0618	0.9382	−0.2433	0.133*	0.49 (4)
H19F	0.1082	1.0858	−0.3096	0.133*	0.49 (4)
H19E	−0.0102	1.0945	−0.1890	0.133*	0.49 (4)
N1	0.16707 (14)	0.88269 (13)	0.45217 (10)	0.0493 (3)
O1	0.16721 (14)	1.03758 (12)	0.43411 (11)	0.0699 (3)
H1A	0.0766	1.0977	0.4635	0.105*
O2	0.52349 (11)	0.61418 (10)	0.24323 (7)	0.0467 (2)
O3	0.99150 (15)	0.67203 (16)	0.05342 (13)	0.0872 (4)
O4	0.93678 (13)	0.49931 (16)	0.20693 (9)	0.0720 (3)

Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0417 (6)	0.0459 (6)	0.0413 (6)	−0.0165 (5)	0.0028 (5)	−0.0081 (5)
C2	0.0363 (5)	0.0416 (6)	0.0369 (5)	−0.0131 (4)	−0.0052 (4)	−0.0034 (4)
C3	0.0498 (7)	0.0526 (7)	0.0433 (6)	−0.0177 (6)	0.0034 (5)	−0.0034 (5)
C4	0.0628 (9)	0.0551 (8)	0.0556 (8)	−0.0281 (7)	0.0009 (7)	0.0061 (6)
C5	0.0620 (8)	0.0428 (6)	0.0639 (8)	−0.0235 (6)	−0.0082 (7)	−0.0009 (6)
C6	0.0480 (7)	0.0427 (6)	0.0502 (7)	−0.0160 (5)	−0.0055 (5)	−0.0095 (5)
C7	0.0366 (5)	0.0407 (6)	0.0362 (5)	−0.0144 (4)	−0.0063 (4)	−0.0032 (4)
C8	0.0453 (6)	0.0428 (6)	0.0431 (6)	−0.0146 (5)	0.0033 (5)	−0.0141 (5)
C9	0.0415 (6)	0.0467 (6)	0.0424 (6)	−0.0162 (5)	0.0055 (5)	−0.0172 (5)
C10	0.0449 (7)	0.0574 (7)	0.0560 (8)	−0.0177 (6)	0.0030 (6)	−0.0205 (6)
C11	0.0524 (9)	0.1224 (16)	0.0710 (11)	−0.0173 (10)	−0.0144 (8)	−0.0242 (11)
C12	0.0462 (7)	0.0483 (6)	0.0483 (7)	−0.0221 (5)	0.0060 (5)	−0.0136 (5)
C13	0.0499 (7)	0.0404 (6)	0.0446 (6)	−0.0181 (5)	0.0019 (5)	−0.0110 (5)
C14	0.0515 (7)	0.0568 (7)	0.0484 (7)	−0.0215 (6)	−0.0001 (6)	−0.0027 (6)
C15	0.0504 (8)	0.0629 (8)	0.0635 (9)	−0.0243 (7)	−0.0030 (6)	−0.0091 (7)
C16	0.0623 (9)	0.0521 (7)	0.0576 (8)	−0.0157 (6)	−0.0123 (7)	−0.0148 (6)
C17	0.0745 (10)	0.0535 (8)	0.0487 (7)	−0.0211 (7)	−0.0075 (7)	−0.0017 (6)
C18	0.0600 (8)	0.0490 (7)	0.0534 (8)	−0.0246 (6)	0.0010 (6)	−0.0029 (6)
C19	0.0806 (13)	0.1011 (15)	0.0808 (12)	−0.0241 (11)	−0.0337 (10)	−0.0105 (11)
N1	0.0485 (6)	0.0423 (5)	0.0524 (6)	−0.0168 (4)	0.0037 (5)	−0.0118 (5)
O1	0.0685 (7)	0.0460 (5)	0.0879 (8)	−0.0241 (5)	0.0180 (6)	−0.0223 (5)
O2	0.0513 (5)	0.0418 (4)	0.0421 (4)	−0.0193 (4)	0.0095 (4)	−0.0118 (3)
O3	0.0586 (7)	0.0883 (9)	0.1159 (11)	−0.0418 (6)	−0.0146 (7)	0.0059 (8)
O4	0.0507 (6)	0.1054 (9)	0.0517 (6)	−0.0264 (6)	−0.0068 (5)	−0.0074 (6)

Geometric parameters (Å, º)

C1—N1	1.2644 (16)	C11—H11B	0.9600
C1—C2	1.4602 (17)	C11—H11C	0.9600
C1—H1	0.9300	C12—C13	1.4566 (19)
C2—C3	1.3879 (17)	C12—H12	0.9300
C2—C7	1.4027 (16)	C13—C14	1.3902 (18)
C3—C4	1.378 (2)	C13—C18	1.3964 (18)
C3—H3	0.9300	C14—C15	1.378 (2)
C4—C5	1.377 (2)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.383 (2)
C5—C6	1.3815 (19)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.380 (2)
C6—C7	1.3860 (17)	C16—C19	1.506 (2)
C6—H6	0.9300	C17—C18	1.370 (2)
C7—O2	1.3618 (14)	C17—H17	0.9300
C8—O2	1.4386 (14)	C18—H18	0.9300
C8—C9	1.4925 (17)	C19—H19A	0.9600
C8—H8A	0.9700	C19—H19B	0.9600
C8—H8B	0.9700	C19—H19C	0.9600
C9—C12	1.3386 (18)	C19—H19D	0.9600
C9—C10	1.4886 (19)	C19—H19F	0.9600
C10—O3	1.1910 (17)	C19—H19E	0.9600
C10—O4	1.3336 (18)	N1—O1	1.4052 (14)
C11—O4	1.443 (2)	O1—H1A	0.8200
C11—H11A	0.9600

N1—C1—C2	120.89 (11)	H11A—C11—H11C	109.5
N1—C1—H1	119.6	H11B—C11—H11C	109.5
C2—C1—H1	119.6	C9—C12—C13	131.50 (12)
C3—C2—C7	118.50 (11)	C9—C12—H12	114.2
C3—C2—C1	122.09 (11)	C13—C12—H12	114.2
C7—C2—C1	119.40 (10)	C14—C13—C18	116.93 (13)
C4—C3—C2	121.16 (13)	C14—C13—C12	125.81 (12)
C4—C3—H3	119.4	C18—C13—C12	117.26 (12)
C2—C3—H3	119.4	C15—C14—C13	121.00 (13)
C5—C4—C3	119.61 (13)	C15—C14—H14	119.5
C5—C4—H4	120.2	C13—C14—H14	119.5
C3—C4—H4	120.2	C14—C15—C16	121.55 (14)
C4—C5—C6	120.81 (13)	C14—C15—H15	119.2
C4—C5—H5	119.6	C16—C15—H15	119.2
C6—C5—H5	119.6	C17—C16—C15	117.63 (14)
C5—C6—C7	119.55 (12)	C17—C16—C19	121.61 (15)
C5—C6—H6	120.2	C15—C16—C19	120.76 (16)
C7—C6—H6	120.2	C18—C17—C16	121.27 (14)
O2—C7—C6	124.60 (11)	C18—C17—H17	119.4
O2—C7—C2	115.05 (10)	C16—C17—H17	119.4
C6—C7—C2	120.35 (11)	C17—C18—C13	121.57 (14)
O2—C8—C9	107.57 (9)	C17—C18—H18	119.2
O2—C8—H8A	110.2	C13—C18—H18	119.2
C9—C8—H8A	110.2	C16—C19—H19A	109.5
O2—C8—H8B	110.2	C16—C19—H19B	109.5
C9—C8—H8B	110.2	C16—C19—H19C	109.5
H8A—C8—H8B	108.5	C16—C19—H19D	109.5
C12—C9—C10	115.91 (12)	C16—C19—H19F	109.5
C12—C9—C8	125.82 (12)	H19D—C19—H19F	109.5
C10—C9—C8	118.27 (11)	C16—C19—H19E	109.5
O3—C10—O4	122.75 (14)	H19D—C19—H19E	109.5
O3—C10—C9	125.04 (14)	H19F—C19—H19E	109.5
O4—C10—C9	112.19 (12)	C1—N1—O1	111.94 (11)
O4—C11—H11A	109.5	N1—O1—H1A	109.5
O4—C11—H11B	109.5	C7—O2—C8	118.77 (9)
H11A—C11—H11B	109.5	C10—O4—C11	116.22 (14)
O4—C11—H11C	109.5

N1—C1—C2—C3	−23.53 (19)	C8—C9—C12—C13	−0.6 (2)
N1—C1—C2—C7	157.62 (12)	C9—C12—C13—C14	20.6 (2)
C7—C2—C3—C4	−1.2 (2)	C9—C12—C13—C18	−159.99 (14)
C1—C2—C3—C4	179.93 (13)	C18—C13—C14—C15	2.5 (2)
C2—C3—C4—C5	0.2 (2)	C12—C13—C14—C15	−178.12 (13)
C3—C4—C5—C6	0.6 (2)	C13—C14—C15—C16	−0.9 (2)
C4—C5—C6—C7	−0.3 (2)	C14—C15—C16—C17	−1.0 (2)
C5—C6—C7—O2	179.27 (12)	C14—C15—C16—C19	178.59 (15)
C5—C6—C7—C2	−0.80 (19)	C15—C16—C17—C18	1.3 (2)
C3—C2—C7—O2	−178.54 (11)	C19—C16—C17—C18	−178.27 (15)
C1—C2—C7—O2	0.35 (16)	C16—C17—C18—C13	0.3 (2)
C3—C2—C7—C6	1.53 (17)	C14—C13—C18—C17	−2.2 (2)
C1—C2—C7—C6	−179.59 (11)	C12—C13—C18—C17	178.37 (13)
O2—C8—C9—C12	−82.19 (15)	C2—C1—N1—O1	178.81 (11)
O2—C8—C9—C10	97.89 (12)	C6—C7—O2—C8	0.84 (17)
C12—C9—C10—O3	−10.0 (2)	C2—C7—O2—C8	−179.09 (10)
C8—C9—C10—O3	169.98 (14)	C9—C8—O2—C7	−170.37 (10)
C12—C9—C10—O4	171.55 (12)	O3—C10—O4—C11	1.0 (2)
C8—C9—C10—O4	−8.52 (16)	C9—C10—O4—C11	179.55 (13)
C10—C9—C12—C13	179.32 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1ⁱ	0.82	2.11	2.8211 (15)	145
C15—H15···O3ⁱⁱ	0.93	2.40	3.247 (2)	151

Symmetry codes: (i) −x, −y+2, −z+1; (ii) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5884).

References

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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