(E)-Methyl 3-(4-ethyl-phen-yl)-2-{2-[(E)-(hy-droxy-imino)-meth-yl]phen-oxy-meth-yl}acrylate.

In the title compound, C(20)H(21)NO(4), the two benzene rings are almost perpendicular to each other, making a dihedral angle of 86.1 (7)°. The hy-droxy-ethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane of the hy-droxy-ethanimine [C=N-OH] group being 0.011 (1) Å for the O atom. An intra-molecular C-H⋯O hydrogen bond occurs. The mol-ecules are linked into cyclic centrosymmetric R(2) (2)(6) dimers via O-H⋯N hydrogen bonds. Inter-molecular C-H⋯O hydrogen bonds link the mol-ecules, forming a C(8) chain along the a axis. The crystal packing is further stabilized by C-H⋯π inter-actions.

Related literature

For structures of other acrylate derivatives, see: Zhang et al. (2009 ▶); Wang et al. (2011 ▶); SakthiMurugesan et al. (2011 ▶). For the use of oxime ligands in coordination chemistry, see: Chaudhuri (2003 ▶).

Experimental

Crystal data

C20H21NO4

M = 339.38

Triclinic,

a = 9.0053 (2) Å

b = 9.3655 (3) Å

c = 12.1793 (3) Å

α = 75.299 (1)°

β = 74.756 (1)°

γ = 64.891 (1)°

V = 885.43 (4) Å3

Z = 2

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

24628 measured reflections

6955 independent reflections

4453 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.189

S = 1.02

6955 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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/S1600536811038359/nk2110sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038359/nk2110Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811038359/nk2110Isup3.cml

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

C20H21NO4	Z = 2
Mr = 339.38	F(000) = 360
Triclinic, P1	Dx = 1.273 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0053 (2) Å	Cell parameters from 6955 reflections
b = 9.3655 (3) Å	θ = 1.8–33.6°
c = 12.1793 (3) Å	µ = 0.09 mm−1
α = 75.299 (1)°	T = 293 K
β = 74.756 (1)°	Block, white
γ = 64.891 (1)°	0.25 × 0.22 × 0.19 mm
V = 885.43 (4) Å3

Bruker APEXII CCD area detector diffractometer	6955 independent reflections
Radiation source: fine-focus sealed tube	4453 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω and φ scans	θmax = 33.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.978, Tmax = 0.983	k = −14→14
24628 measured reflections	l = −18→18

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) = 0.189	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.1052P)2 + 0.0753P] where P = (Fo2 + 2Fc2)/3
6955 reflections	(Δ/σ)max < 0.001
229 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.29 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	−0.16884 (13)	0.61894 (13)	0.41644 (9)	0.0372 (2)
C2	−0.25120 (16)	0.53924 (17)	0.50619 (11)	0.0506 (3)
H2	−0.3220	0.5916	0.5669	0.061*
C3	−0.23045 (18)	0.38465 (18)	0.50735 (13)	0.0587 (4)
H3	−0.2877	0.3337	0.5677	0.070*
C4	−0.12419 (17)	0.30617 (16)	0.41841 (13)	0.0533 (3)
H4	−0.1100	0.2017	0.4190	0.064*
C5	−0.03793 (15)	0.38050 (15)	0.32794 (11)	0.0444 (3)
H5	0.0334	0.3263	0.2682	0.053*
C6	−0.05852 (12)	0.53598 (13)	0.32705 (9)	0.0354 (2)
C7	−0.19037 (14)	0.78288 (14)	0.41442 (10)	0.0411 (2)
H7	−0.1036	0.8170	0.3784	0.049*
C8	0.13999 (13)	0.54048 (14)	0.15190 (10)	0.0404 (2)
H8A	0.0841	0.5207	0.1027	0.048*
H8B	0.2179	0.4387	0.1839	0.048*
C9	0.23062 (13)	0.64543 (14)	0.08369 (9)	0.0376 (2)
C10	0.39509 (14)	0.61395 (15)	0.11024 (10)	0.0420 (3)
C11	0.58541 (18)	0.4676 (2)	0.23780 (14)	0.0680 (4)
H11A	0.6696	0.4611	0.1697	0.102*
H11B	0.6146	0.3663	0.2880	0.102*
H11C	0.5773	0.5483	0.2769	0.102*
C12	0.17940 (13)	0.76549 (14)	−0.00239 (10)	0.0400 (2)
H12	0.2523	0.8176	−0.0358	0.048*
C13	0.02946 (14)	0.82890 (14)	−0.05290 (10)	0.0389 (2)
C14	−0.11884 (15)	0.80690 (17)	−0.00057 (11)	0.0474 (3)
H14	−0.1272	0.7486	0.0734	0.057*
C15	−0.25321 (16)	0.87026 (18)	−0.05692 (12)	0.0516 (3)
H15	−0.3495	0.8518	−0.0205	0.062*
C16	−0.24822 (16)	0.96077 (15)	−0.16646 (11)	0.0459 (3)
C17	−0.10288 (17)	0.98621 (16)	−0.21751 (11)	0.0492 (3)
H17	−0.0966	1.0479	−0.2903	0.059*
C18	0.03252 (15)	0.92197 (15)	−0.16260 (11)	0.0468 (3)
H18	0.1284	0.9410	−0.1994	0.056*
C19	−0.3973 (2)	1.0316 (2)	−0.22612 (15)	0.0637 (4)
H19A	−0.4829	1.1184	−0.1881	0.076*
H19B	−0.3646	1.0766	−0.3051	0.076*
C20	−0.4694 (3)	0.9162 (3)	−0.2271 (2)	0.0898 (7)
H20A	−0.3902	0.8366	−0.2726	0.135*
H20B	−0.5691	0.9716	−0.2597	0.135*
H20C	−0.4954	0.8656	−0.1496	0.135*
N1	−0.32728 (13)	0.87907 (12)	0.46171 (9)	0.0449 (2)
O1	−0.32289 (13)	1.02929 (12)	0.45450 (10)	0.0588 (3)
H1	−0.4168	1.0924	0.4764	0.088*
O2	0.01993 (10)	0.62061 (9)	0.24319 (7)	0.0415 (2)
O3	0.42776 (12)	0.50810 (14)	0.20593 (8)	0.0585 (3)
O4	0.49093 (12)	0.67314 (14)	0.05241 (10)	0.0682 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0339 (4)	0.0404 (5)	0.0323 (5)	−0.0132 (4)	−0.0039 (4)	−0.0013 (4)
C2	0.0490 (6)	0.0528 (7)	0.0386 (6)	−0.0196 (5)	0.0047 (5)	−0.0010 (5)
C3	0.0605 (8)	0.0540 (8)	0.0535 (8)	−0.0303 (6)	0.0014 (6)	0.0081 (6)
C4	0.0555 (7)	0.0415 (6)	0.0603 (8)	−0.0233 (5)	−0.0075 (6)	0.0018 (6)
C5	0.0447 (6)	0.0403 (6)	0.0466 (6)	−0.0179 (5)	−0.0036 (5)	−0.0063 (5)
C6	0.0327 (4)	0.0379 (5)	0.0325 (5)	−0.0136 (4)	−0.0053 (4)	−0.0010 (4)
C7	0.0406 (5)	0.0453 (6)	0.0345 (5)	−0.0171 (4)	−0.0008 (4)	−0.0064 (4)
C8	0.0390 (5)	0.0399 (6)	0.0396 (6)	−0.0159 (4)	0.0031 (4)	−0.0110 (4)
C9	0.0359 (5)	0.0424 (6)	0.0343 (5)	−0.0167 (4)	0.0024 (4)	−0.0119 (4)
C10	0.0379 (5)	0.0475 (6)	0.0390 (6)	−0.0158 (5)	−0.0017 (4)	−0.0107 (5)
C11	0.0469 (7)	0.0909 (12)	0.0560 (9)	−0.0153 (7)	−0.0158 (6)	−0.0077 (8)
C12	0.0379 (5)	0.0447 (6)	0.0386 (6)	−0.0193 (4)	−0.0002 (4)	−0.0090 (4)
C13	0.0404 (5)	0.0404 (6)	0.0371 (5)	−0.0178 (4)	−0.0027 (4)	−0.0085 (4)
C14	0.0444 (6)	0.0608 (7)	0.0360 (6)	−0.0254 (5)	−0.0049 (4)	0.0009 (5)
C15	0.0445 (6)	0.0660 (8)	0.0458 (7)	−0.0289 (6)	−0.0081 (5)	0.0021 (6)
C16	0.0494 (6)	0.0448 (6)	0.0456 (6)	−0.0199 (5)	−0.0126 (5)	−0.0032 (5)
C17	0.0578 (7)	0.0466 (7)	0.0417 (6)	−0.0251 (6)	−0.0094 (5)	0.0052 (5)
C18	0.0466 (6)	0.0471 (7)	0.0460 (6)	−0.0244 (5)	−0.0041 (5)	0.0008 (5)
C19	0.0647 (9)	0.0652 (9)	0.0617 (9)	−0.0253 (7)	−0.0287 (7)	0.0077 (7)
C20	0.0947 (13)	0.1082 (15)	0.0893 (13)	−0.0635 (12)	−0.0580 (11)	0.0331 (11)
N1	0.0464 (5)	0.0425 (5)	0.0423 (5)	−0.0165 (4)	0.0006 (4)	−0.0104 (4)
O1	0.0607 (6)	0.0479 (5)	0.0677 (7)	−0.0234 (4)	0.0043 (5)	−0.0207 (5)
O2	0.0445 (4)	0.0389 (4)	0.0361 (4)	−0.0188 (3)	0.0074 (3)	−0.0080 (3)
O3	0.0459 (5)	0.0795 (7)	0.0437 (5)	−0.0238 (5)	−0.0092 (4)	0.0013 (5)
O4	0.0510 (5)	0.0811 (7)	0.0752 (7)	−0.0386 (5)	−0.0171 (5)	0.0124 (6)

C1—C2	1.3898 (15)	C11—H11B	0.9600
C1—C6	1.4076 (15)	C11—H11C	0.9600
C1—C7	1.4582 (17)	C12—C13	1.4579 (16)
C2—C3	1.376 (2)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.3969 (15)
C3—C4	1.375 (2)	C13—C18	1.3984 (16)
C3—H3	0.9300	C14—C15	1.3812 (18)
C4—C5	1.3862 (17)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.3883 (18)
C5—C6	1.3851 (16)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.3848 (18)
C6—O2	1.3621 (12)	C16—C19	1.5112 (19)
C7—N1	1.2692 (15)	C17—C18	1.3777 (19)
C7—H7	0.9300	C17—H17	0.9300
C8—O2	1.4392 (13)	C18—H18	0.9300
C8—C9	1.4940 (15)	C19—C20	1.482 (2)
C8—H8A	0.9700	C19—H19A	0.9700
C8—H8B	0.9700	C19—H19B	0.9700
C9—C12	1.3387 (17)	C20—H20A	0.9600
C9—C10	1.4893 (16)	C20—H20B	0.9600
C10—O4	1.1985 (14)	C20—H20C	0.9600
C10—O3	1.3320 (16)	N1—O1	1.4039 (14)
C11—O3	1.4380 (17)	O1—H1	0.8200
C11—H11A	0.9600
C2—C1—C6	118.34 (11)	H11B—C11—H11C	109.5
C2—C1—C7	121.91 (10)	C9—C12—C13	131.31 (10)
C6—C1—C7	119.73 (9)	C9—C12—H12	114.3
C3—C2—C1	121.56 (12)	C13—C12—H12	114.3
C3—C2—H2	119.2	C14—C13—C18	116.77 (11)
C1—C2—H2	119.2	C14—C13—C12	125.70 (11)
C4—C3—C2	119.34 (12)	C18—C13—C12	117.53 (10)
C4—C3—H3	120.3	C15—C14—C13	121.07 (11)
C2—C3—H3	120.3	C15—C14—H14	119.5
C3—C4—C5	120.98 (12)	C13—C14—H14	119.5
C3—C4—H4	119.5	C14—C15—C16	121.71 (11)
C5—C4—H4	119.5	C14—C15—H15	119.1
C6—C5—C4	119.63 (12)	C16—C15—H15	119.1
C6—C5—H5	120.2	C17—C16—C15	117.40 (12)
C4—C5—H5	120.2	C17—C16—C19	121.52 (12)
O2—C6—C5	124.79 (10)	C15—C16—C19	121.07 (12)
O2—C6—C1	115.07 (10)	C18—C17—C16	121.33 (12)
C5—C6—C1	120.13 (10)	C18—C17—H17	119.3
N1—C7—C1	120.10 (10)	C16—C17—H17	119.3
N1—C7—H7	120.0	C17—C18—C13	121.68 (11)
C1—C7—H7	120.0	C17—C18—H18	119.2
O2—C8—C9	108.04 (9)	C13—C18—H18	119.2
O2—C8—H8A	110.1	C20—C19—C16	114.28 (13)
C9—C8—H8A	110.1	C20—C19—H19A	108.7
O2—C8—H8B	110.1	C16—C19—H19A	108.7
C9—C8—H8B	110.1	C20—C19—H19B	108.7
H8A—C8—H8B	108.4	C16—C19—H19B	108.7
C12—C9—C10	115.74 (10)	H19A—C19—H19B	107.6
C12—C9—C8	125.94 (11)	C19—C20—H20A	109.5
C10—C9—C8	118.30 (10)	C19—C20—H20B	109.5
O4—C10—O3	122.56 (11)	H20A—C20—H20B	109.5
O4—C10—C9	125.05 (12)	C19—C20—H20C	109.5
O3—C10—C9	112.38 (10)	H20A—C20—H20C	109.5
O3—C11—H11A	109.5	H20B—C20—H20C	109.5
O3—C11—H11B	109.5	C7—N1—O1	111.99 (10)
H11A—C11—H11B	109.5	N1—O1—H1	109.5
O3—C11—H11C	109.5	C6—O2—C8	117.90 (9)
H11A—C11—H11C	109.5	C10—O3—C11	116.58 (11)
C6—C1—C2—C3	−1.8 (2)	C9—C12—C13—C14	19.8 (2)
C7—C1—C2—C3	179.87 (13)	C9—C12—C13—C18	−161.25 (12)
C1—C2—C3—C4	0.8 (2)	C18—C13—C14—C15	2.05 (19)
C2—C3—C4—C5	0.0 (2)	C12—C13—C14—C15	−178.95 (13)
C3—C4—C5—C6	0.2 (2)	C13—C14—C15—C16	−1.3 (2)
C4—C5—C6—O2	179.74 (12)	C14—C15—C16—C17	−0.3 (2)
C4—C5—C6—C1	−1.19 (18)	C14—C15—C16—C19	−178.94 (14)
C2—C1—C6—O2	−178.86 (11)	C15—C16—C17—C18	1.1 (2)
C7—C1—C6—O2	−0.51 (15)	C19—C16—C17—C18	179.70 (13)
C2—C1—C6—C5	1.98 (17)	C16—C17—C18—C13	−0.3 (2)
C7—C1—C6—C5	−179.66 (11)	C14—C13—C18—C17	−1.29 (19)
C2—C1—C7—N1	−30.13 (18)	C12—C13—C18—C17	179.63 (12)
C6—C1—C7—N1	151.58 (11)	C17—C16—C19—C20	131.30 (18)
O2—C8—C9—C12	−84.39 (14)	C15—C16—C19—C20	−50.1 (2)
O2—C8—C9—C10	97.11 (11)	C1—C7—N1—O1	177.99 (10)
C12—C9—C10—O4	−9.75 (18)	C5—C6—O2—C8	−3.60 (16)
C8—C9—C10—O4	168.90 (12)	C1—C6—O2—C8	177.30 (9)
C12—C9—C10—O3	171.59 (10)	C9—C8—O2—C6	−169.80 (9)
C8—C9—C10—O3	−9.75 (15)	O4—C10—O3—C11	0.3 (2)
C10—C9—C12—C13	179.15 (11)	C9—C10—O3—C11	178.95 (12)
C8—C9—C12—C13	0.6 (2)

Cg2 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	2.15	2.8568 (15)	145.
C8—H8B···O3	0.97	2.34	2.7146 (18)	102
C12—H12···O4	0.93	2.37	2.7742 (18)	106
C14—H14···O2	0.93	2.51	3.3002 (16)	143
C15—H15···O4ii	0.93	2.50	3.3524 (16)	152.
C5—H5···Cg2iii	0.93	2.94	3.7756 (14)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	2.15	2.8568 (15)	145
C14—H14⋯O2	0.93	2.51	3.3002 (16)	143
C15—H15⋯O4ii	0.93	2.50	3.3524 (16)	152
C5—H5⋯Cg2iii	0.93	2.94	3.7756 (14)	150

Symmetry codes: (i) ; (ii) ; (iii) .