(E)-Methyl 2-({2-eth­oxy-6-[(E)-(hy­droxy­imino)­meth­yl]phen­oxy}meth­yl)-3-phenyl­acrylate

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

doi:10.1107/S1600536812014596

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1373

doi:10.1107/S1600536812014596

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(E)-Methyl 2-({2-ethoxy-6-[(E)-(hydroxyimino)methyl]phenoxy}methyl)-3-phenylacrylate

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

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^bDepartment of Physics, SMK Fomra Institute of Technology, Thaiyur, Chennai 603 103, India, and ^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: a_sp59@yahoo.in

(Received 5 January 2012; accepted 4 April 2012; online 13 April 2012)

In the title compound, C₂₀H₂₁NO₅, the dihedral angle between the mean planes through the two rings is 47.1 (8)°. 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 0.061 (1) Å for the O atom. In the crystal, molecules are linked into cyclic centrosymmetric dimers with an R₂²(6) motif via pairs of O—H⋯N hydrogen bonds. Intermolecular C—H⋯O hydrogen bonds form a C(8) chain along the b axis. The crystal packing is further stabilized by C—H⋯π interactions.

Related literature

For the biological activity of caffeic acids and their esters, see: Hwang et al. (2001 ); Altug et al. (2008 ); Ates et al. (2006 ); Atik et al. (2006 ); Chaudhuri (2003 ); Padinchare et al. (2001 ). For a related structure, see: SakthiMurugesan et al. (2011 ). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₂₁NO₅
M_r = 355.38
Monoclinic, P 2₁ /n
a = 7.4009 (3) Å
b = 22.1125 (10) Å
c = 11.3681 (5) Å
β = 103.561 (1)°
V = 1808.55 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.09 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
25247 measured reflections
6042 independent reflections
4293 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.167
S = 1.02
6042 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1ⁱ	0.82	2.08	2.8121 (15)	149
C4—H4⋯O4ⁱⁱ	0.93	2.59	3.2379 (18)	127
C20—H20⋯O1ⁱⁱⁱ	0.93	2.59	3.466 (2)	157
C9—H9B⋯Cg2^iv	0.96	2.79	3.616 (2)	145
Symmetry codes: (i) -x+2, -y, -z+2; (ii) -x+1, -y, -z+2; (iii) -x+1, -y, -z+1; (iv) $[x-{\script{3\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536812014596/rn2100sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014596/rn2100Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812014596/rn2100Isup3.cml

checkCIF report

Comment top

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 anti-inflammatory properties (Atik et al., 2006; Padinchare et al., 2001; Ates et al., 2006). Oximes are a classical type of chelating ligand which are widely used in coordination and analytical chemistry (Chaudhuri, 2003).

In the title compound (see Fig. 1) the bond lengths and angles 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 47.1 (8)°. The oxime C—N has an E configuration. The hydroxyethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane being 0.004 (1) Å for the C2 atom.

The ether group assumes an extended conformation as can be seen from torsion angles C11—C12—O5—C13 [-174.7 (1) °] and C10—C11—C12—O5 [170.7 (1) °]. C—H···O hydrogen bonds (see Table 1) form C(8) chains along (Bernstein et al. 1995) the b axis. The hydroxyethanimine group in the molecules are linked into cyclic centrosymmetric dimers via O—H···N hydrogen bonds with the R₂²(6) motif. The closest C—H-centroid separation is 3.6 Å therefore there are not significant C—H···π interactions. In addition to van der Waals interactions the crystal packing is stabilized by C–H···O and O–H···N interactions.

Related literature top

For the biological activity of caffeic acids and their esters, see: Hwang et al. (2001); Altug et al. (2008); Ates et al. (2006); Atik et al. (2006); Chaudhuri (2003); Padinchare et al. (2001). For a related structure, see: SakthiMurugesan et al. (2011). For graph-set analysis of hydrogen bonds, see; Bernstein et al. (1995).

Experimental top

To a stirred solution of (E)-methyl 2-((2-ethoxy-6-formylphenoxy)methyl) -3-phenylacrylate (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 (E)-methyl2-((2-ethoxy- 6-((E)-(hydroxyimino)methyl)phenoxy)methyl)-3-phenylacrylate 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 (2-x, -y, 2-z). The dashed lines indicate the hydrogen bonds.

(E)-Methyl 2-({2-ethoxy-6-[(E)-(hydroxyimino)methyl]phenoxy}methyl)-3-phenylacrylate top

Crystal data top

C₂₀H₂₁NO₅	F(000) = 752
M_r = 355.38	D_x = 1.305 Mg m⁻³ D_m = 1.375 Mg m⁻³ D_m measured by not measured
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6042 reflections
a = 7.4009 (3) Å	θ = 1.8–31.6°
b = 22.1125 (10) Å	µ = 0.09 mm⁻¹
c = 11.3681 (5) Å	T = 293 K
β = 103.561 (1)°	Block, white crystalline
V = 1808.55 (14) Å³	0.25 × 0.22 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII CCD area detector diffractometer	6042 independent reflections
Radiation source: fine-focus sealed tube	4293 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scans	θ_max = 31.6°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.978, T_max = 0.983	k = −32→32
25247 measured reflections	l = −14→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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0873P)² + 0.3814P] where P = (F_o² + 2F_c²)/3
6042 reflections	(Δ/σ)_max < 0.001
238 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₀H₂₁NO₅	V = 1808.55 (14) Å³
M_r = 355.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.4009 (3) Å	µ = 0.09 mm⁻¹
b = 22.1125 (10) Å	T = 293 K
c = 11.3681 (5) Å	0.25 × 0.22 × 0.19 mm
β = 103.561 (1)°

Data collection top

Bruker APEXII CCD area detector diffractometer	6042 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4293 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.983	R_int = 0.027
25247 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.02	Δρ_max = 0.50 e Å⁻³
6042 reflections	Δρ_min = −0.24 e Å⁻³
238 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	0.66305 (18)	0.04722 (6)	0.86324 (12)	0.0369 (3)
H1	0.6348	0.0414	0.7799	0.044*
C2	0.52766 (17)	0.07679 (6)	0.91943 (11)	0.0313 (2)
C3	0.5530 (2)	0.08059 (6)	1.04563 (12)	0.0385 (3)
H3	0.6589	0.0641	1.0960	0.046*
C4	0.4225 (2)	0.10847 (7)	1.09493 (12)	0.0423 (3)
H4	0.4392	0.1097	1.1786	0.051*
C5	0.2661 (2)	0.13482 (7)	1.02182 (13)	0.0415 (3)
H5	0.1791	0.1539	1.0563	0.050*
C6	0.23961 (18)	0.13273 (6)	0.89702 (11)	0.0337 (3)
C7	0.36826 (16)	0.10210 (5)	0.84560 (10)	0.0291 (2)
C8	−0.0070 (3)	0.20593 (10)	0.86177 (17)	0.0632 (5)
H8A	0.0740	0.2293	0.9250	0.076*
H8B	−0.1026	0.1872	0.8951	0.076*
C9	−0.0933 (3)	0.24597 (10)	0.7579 (2)	0.0772 (6)
H9A	0.0013	0.2608	0.7202	0.116*
H9B	−0.1532	0.2795	0.7867	0.116*
H9C	−0.1834	0.2234	0.7000	0.116*
C10	0.17647 (18)	0.06976 (7)	0.65716 (11)	0.0372 (3)
H10A	0.0762	0.0989	0.6349	0.045*
H10B	0.1401	0.0393	0.7085	0.045*
C11	0.21243 (17)	0.04080 (6)	0.54594 (11)	0.0329 (3)
C12	0.28726 (19)	−0.02179 (7)	0.56460 (13)	0.0388 (3)
C13	0.3504 (3)	−0.11301 (8)	0.4760 (2)	0.0604 (5)
H13A	0.4669	−0.1161	0.5346	0.091*
H13B	0.3642	−0.1283	0.3996	0.091*
H13C	0.2580	−0.1362	0.5028	0.091*
C14	0.17680 (17)	0.06620 (6)	0.43559 (11)	0.0335 (3)
H14	0.2015	0.0421	0.3742	0.040*
C15	0.10419 (17)	0.12684 (6)	0.39869 (11)	0.0335 (3)
C16	0.1278 (2)	0.17773 (7)	0.47358 (14)	0.0432 (3)
H16	0.1968	0.1747	0.5531	0.052*
C17	0.0490 (2)	0.23275 (7)	0.43013 (16)	0.0513 (4)
H17	0.0651	0.2663	0.4808	0.062*
C18	−0.0529 (2)	0.23794 (8)	0.31254 (17)	0.0531 (4)
H18	−0.1072	0.2747	0.2844	0.064*
C19	−0.0744 (2)	0.18858 (8)	0.23667 (15)	0.0522 (4)
H19	−0.1420	0.1921	0.1570	0.063*
C20	0.0045 (2)	0.13382 (7)	0.27890 (13)	0.0422 (3)
H20	−0.0091	0.1009	0.2266	0.051*
N1	0.81897 (15)	0.02940 (6)	0.92689 (10)	0.0383 (3)
O1	0.92841 (16)	0.00226 (6)	0.85611 (10)	0.0534 (3)
H1A	1.0254	−0.0101	0.9001	0.080*
O2	0.09792 (15)	0.16043 (5)	0.81645 (9)	0.0468 (3)
O3	0.34510 (11)	0.09991 (4)	0.72187 (7)	0.0319 (2)
O4	0.3345 (2)	−0.04452 (6)	0.66304 (12)	0.0700 (4)
O5	0.29384 (17)	−0.05077 (5)	0.46293 (10)	0.0503 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0359 (6)	0.0413 (7)	0.0303 (6)	0.0062 (5)	0.0017 (5)	−0.0023 (5)
C2	0.0332 (5)	0.0295 (6)	0.0281 (5)	0.0018 (4)	0.0011 (4)	−0.0014 (4)
C3	0.0446 (7)	0.0380 (7)	0.0282 (6)	0.0048 (5)	−0.0008 (5)	0.0006 (5)
C4	0.0565 (8)	0.0434 (7)	0.0256 (6)	0.0044 (6)	0.0067 (5)	−0.0007 (5)
C5	0.0496 (8)	0.0433 (7)	0.0336 (7)	0.0087 (6)	0.0140 (6)	−0.0007 (5)
C6	0.0362 (6)	0.0328 (6)	0.0312 (6)	0.0052 (5)	0.0061 (5)	0.0005 (5)
C7	0.0319 (5)	0.0292 (5)	0.0247 (5)	0.0005 (4)	0.0038 (4)	0.0003 (4)
C8	0.0637 (10)	0.0767 (13)	0.0540 (10)	0.0377 (10)	0.0236 (8)	0.0090 (9)
C9	0.0768 (14)	0.0746 (14)	0.0834 (15)	0.0377 (11)	0.0253 (12)	0.0154 (11)
C10	0.0307 (6)	0.0521 (8)	0.0277 (6)	−0.0065 (5)	0.0046 (4)	−0.0026 (5)
C11	0.0293 (5)	0.0399 (6)	0.0274 (6)	−0.0034 (5)	0.0021 (4)	−0.0004 (5)
C12	0.0347 (6)	0.0416 (7)	0.0364 (7)	−0.0033 (5)	0.0007 (5)	0.0059 (5)
C13	0.0545 (9)	0.0386 (8)	0.0902 (14)	0.0061 (7)	0.0213 (9)	0.0016 (8)
C14	0.0353 (6)	0.0363 (6)	0.0275 (6)	0.0001 (5)	0.0044 (5)	−0.0028 (5)
C15	0.0321 (5)	0.0375 (6)	0.0300 (6)	0.0007 (5)	0.0058 (4)	−0.0004 (5)
C16	0.0461 (7)	0.0426 (8)	0.0376 (7)	0.0019 (6)	0.0030 (6)	−0.0063 (6)
C17	0.0570 (9)	0.0411 (8)	0.0550 (9)	0.0062 (7)	0.0117 (7)	−0.0097 (7)
C18	0.0524 (9)	0.0442 (8)	0.0607 (10)	0.0163 (7)	0.0091 (7)	0.0044 (7)
C19	0.0556 (9)	0.0531 (9)	0.0410 (8)	0.0107 (7)	−0.0023 (7)	0.0050 (7)
C20	0.0507 (8)	0.0405 (7)	0.0318 (6)	0.0032 (6)	0.0023 (6)	−0.0018 (5)
N1	0.0344 (5)	0.0451 (6)	0.0338 (5)	0.0073 (4)	0.0043 (4)	−0.0037 (5)
O1	0.0444 (6)	0.0776 (8)	0.0371 (5)	0.0225 (5)	0.0070 (4)	−0.0060 (5)
O2	0.0454 (5)	0.0547 (6)	0.0384 (5)	0.0229 (5)	0.0059 (4)	0.0001 (4)
O3	0.0299 (4)	0.0403 (5)	0.0238 (4)	−0.0013 (3)	0.0032 (3)	0.0005 (3)
O4	0.0975 (11)	0.0573 (8)	0.0452 (7)	0.0093 (7)	−0.0035 (7)	0.0172 (6)
O5	0.0609 (7)	0.0410 (6)	0.0482 (6)	0.0104 (5)	0.0109 (5)	0.0010 (5)

Geometric parameters (Å, º) top

C1—N1	1.2723 (16)	C10—H10B	0.9700
C1—C2	1.4627 (18)	C11—C14	1.3429 (18)
C1—H1	0.9300	C11—C12	1.487 (2)
C2—C7	1.3947 (16)	C12—O4	1.2014 (17)
C2—C3	1.4051 (18)	C12—O5	1.3324 (19)
C3—C4	1.371 (2)	C13—O5	1.436 (2)
C3—H3	0.9300	C13—H13A	0.9600
C4—C5	1.385 (2)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
C5—C6	1.3866 (19)	C14—C15	1.4687 (18)
C5—H5	0.9300	C14—H14	0.9300
C6—O2	1.3650 (15)	C15—C20	1.3970 (18)
C6—C7	1.4029 (17)	C15—C16	1.3971 (19)
C7—O3	1.3774 (14)	C16—C17	1.389 (2)
C8—O2	1.4382 (19)	C16—H16	0.9300
C8—C9	1.494 (3)	C17—C18	1.377 (2)
C8—H8A	0.9700	C17—H17	0.9300
C8—H8B	0.9700	C18—C19	1.377 (2)
C9—H9A	0.9600	C18—H18	0.9300
C9—H9B	0.9600	C19—C20	1.381 (2)
C9—H9C	0.9600	C19—H19	0.9300
C10—O3	1.4536 (15)	C20—H20	0.9300
C10—C11	1.4957 (18)	N1—O1	1.4034 (15)
C10—H10A	0.9700	O1—H1A	0.8200

N1—C1—C2	120.86 (12)	C14—C11—C12	120.50 (12)
N1—C1—H1	119.6	C14—C11—C10	125.14 (13)
C2—C1—H1	119.6	C12—C11—C10	114.32 (11)
C7—C2—C3	118.81 (12)	O4—C12—O5	123.03 (15)
C7—C2—C1	119.08 (11)	O4—C12—C11	122.64 (15)
C3—C2—C1	122.11 (11)	O5—C12—C11	114.32 (12)
C4—C3—C2	120.40 (12)	O5—C13—H13A	109.5
C4—C3—H3	119.8	O5—C13—H13B	109.5
C2—C3—H3	119.8	H13A—C13—H13B	109.5
C3—C4—C5	120.89 (12)	O5—C13—H13C	109.5
C3—C4—H4	119.6	H13A—C13—H13C	109.5
C5—C4—H4	119.6	H13B—C13—H13C	109.5
C4—C5—C6	119.84 (13)	C11—C14—C15	128.85 (12)
C4—C5—H5	120.1	C11—C14—H14	115.6
C6—C5—H5	120.1	C15—C14—H14	115.6
O2—C6—C5	125.00 (12)	C20—C15—C16	117.84 (13)
O2—C6—C7	115.26 (11)	C20—C15—C14	116.97 (12)
C5—C6—C7	119.70 (12)	C16—C15—C14	125.18 (12)
O3—C7—C2	119.05 (11)	C17—C16—C15	120.45 (14)
O3—C7—C6	120.55 (10)	C17—C16—H16	119.8
C2—C7—C6	120.27 (11)	C15—C16—H16	119.8
O2—C8—C9	107.33 (15)	C18—C17—C16	120.46 (15)
O2—C8—H8A	110.2	C18—C17—H17	119.8
C9—C8—H8A	110.2	C16—C17—H17	119.8
O2—C8—H8B	110.2	C17—C18—C19	119.90 (15)
C9—C8—H8B	110.2	C17—C18—H18	120.1
H8A—C8—H8B	108.5	C19—C18—H18	120.1
C8—C9—H9A	109.5	C18—C19—C20	120.01 (15)
C8—C9—H9B	109.5	C18—C19—H19	120.0
H9A—C9—H9B	109.5	C20—C19—H19	120.0
C8—C9—H9C	109.5	C19—C20—C15	121.30 (14)
H9A—C9—H9C	109.5	C19—C20—H20	119.4
H9B—C9—H9C	109.5	C15—C20—H20	119.4
O3—C10—C11	108.81 (10)	C1—N1—O1	112.01 (11)
O3—C10—H10A	109.9	N1—O1—H1A	109.5
C11—C10—H10A	109.9	C6—O2—C8	117.90 (12)
O3—C10—H10B	109.9	C7—O3—C10	114.80 (9)
C11—C10—H10B	109.9	C12—O5—C13	116.09 (14)
H10A—C10—H10B	108.3

N1—C1—C2—C7	172.39 (13)	C12—C11—C14—C15	−179.71 (12)
N1—C1—C2—C3	−7.6 (2)	C10—C11—C14—C15	2.7 (2)
C7—C2—C3—C4	0.3 (2)	C11—C14—C15—C20	−152.45 (14)
C1—C2—C3—C4	−179.74 (14)	C11—C14—C15—C16	27.8 (2)
C2—C3—C4—C5	−1.8 (2)	C20—C15—C16—C17	1.9 (2)
C3—C4—C5—C6	0.5 (2)	C14—C15—C16—C17	−178.35 (14)
C4—C5—C6—O2	−175.45 (14)	C15—C16—C17—C18	−0.2 (3)
C4—C5—C6—C7	2.2 (2)	C16—C17—C18—C19	−1.1 (3)
C3—C2—C7—O3	178.30 (11)	C17—C18—C19—C20	0.7 (3)
C1—C2—C7—O3	−1.65 (18)	C18—C19—C20—C15	1.1 (3)
C3—C2—C7—C6	2.38 (19)	C16—C15—C20—C19	−2.4 (2)
C1—C2—C7—C6	−177.57 (12)	C14—C15—C20—C19	177.90 (15)
O2—C6—C7—O3	−1.64 (18)	C2—C1—N1—O1	179.96 (12)
C5—C6—C7—O3	−179.51 (12)	C5—C6—O2—C8	14.9 (2)
O2—C6—C7—C2	174.22 (12)	C7—C6—O2—C8	−162.82 (15)
C5—C6—C7—C2	−3.7 (2)	C9—C8—O2—C6	156.80 (17)
O3—C10—C11—C14	−93.89 (15)	C2—C7—O3—C10	122.08 (13)
O3—C10—C11—C12	88.35 (13)	C6—C7—O3—C10	−62.01 (15)
C14—C11—C12—O4	174.10 (15)	C11—C10—O3—C7	−149.29 (11)
C10—C11—C12—O4	−8.0 (2)	O4—C12—O5—C13	3.8 (2)
C14—C11—C12—O5	−7.17 (18)	C11—C12—O5—C13	−174.95 (13)
C10—C11—C12—O5	170.71 (11)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1ⁱ	0.82	2.08	2.8121 (15)	149
C4—H4···O4ⁱⁱ	0.93	2.59	3.2379 (18)	127
C20—H20···O1ⁱⁱⁱ	0.93	2.59	3.466 (2)	157
C9—H9B···Cg2^iv	0.96	2.79	3.616 (2)	145

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+1, −y, −z+2; (iii) −x+1, −y, −z+1; (iv) x−3/2, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₁NO₅
M_r	355.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.4009 (3), 22.1125 (10), 11.3681 (5)
β (°)	103.561 (1)
V (Å³)	1808.55 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
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	25247, 6042, 4293
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.737

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.167, 1.02
No. of reflections	6042
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.24

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

Cg2 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1ⁱ	0.82	2.08	2.8121 (15)	149.1
C4—H4···O4ⁱⁱ	0.93	2.59	3.2379 (18)	127.1
C20—H20···O1ⁱⁱⁱ	0.93	2.59	3.466 (2)	157.2
C9—H9B···Cg2^iv	0.96	2.79	3.616 (2)	145

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+1, −y, −z+2; (iii) −x+1, −y, −z+1; (iv) x−3/2, −y−1/2, z−1/2.

Acknowledgements

EG and ASP thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

References

Altug, M. E., Serarslan, Y. & Bal, R. (2008). Brain Res. 1201, 135–142. Web of Science PubMed CAS Google Scholar
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(E)-Methyl 2-({2-eth­­oxy-6-[(E)-(hy­dr­oxy­imino)­meth­yl]phen­­oxy}meth­yl)-3-phenyl­acrylate

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(E)-Methyl 2-({2-ethoxy-6-[(E)-(hydroxyimino)methyl]phenoxy}methyl)-3-phenylacrylate