(E)-Methyl 2-({2-eth-oxy-6-[(E)-(hy-droxy-imino)-meth-yl]phen-oxy}meth-yl)-3-phenyl-acrylate.

In the title compound, C(20)H(21)NO(5), the dihedral angle between the mean planes through the two rings is 47.1 (8)°. The enoate group assumes an extended conformation. The hy-droxy-ethanimine 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, mol-ecules are linked into cyclic centrosymmetric dimers with an R(2) (2)(6) motif via pairs of O-H⋯N hydrogen bonds. Inter-molecular C-H⋯O hydrogen bonds form a C(8) chain along the b axis. The crystal packing is further stabilized by C-H⋯π inter-actions.

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 = 355.38

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.167

S = 1.02

6042 reflections

238 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.24 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: 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/S1600536812014596/rn2100sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812014596/rn2100Isup3.cml

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

C20H21NO5	F(000) = 752
Mr = 355.38	Dx = 1.305 Mg m−3Dm = 1.375 Mg m−3Dm 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

Bruker APEXII CCD area detector diffractometer	6042 independent reflections
Radiation source: fine-focus sealed tube	4293 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scans	θmax = 31.6°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.978, Tmax = 0.983	k = −32→32
25247 measured reflections	l = −14→16

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(Fo2) + (0.0873P)2 + 0.3814P] where P = (Fo2 + 2Fc2)/3
6042 reflections	(Δ/σ)max < 0.001
238 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.24 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	0.66305 (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)

	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)

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)

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···Cg2iv	0.96	2.79	3.616 (2)	145

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⋯Cg2iv	0.96	2.79	3.616 (2)	145

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