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

In the title compound, C(18)H(17)NO(4), the hy-droxy-ethanimine group is essentially coplanar with the ring to which it is attached [C-C-N-O torsion angle = 179.94 (14)°]. The mol-ecules are linked into cyclic centrosymmetric R(2) (2)(6) dimers via O-H⋯N hydrogen bonds and the crystal packing is further stabilized by C-H⋯O inter-actions.

Related literature

For 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

C18H17NO4

M = 311.33

Monoclinic,

a = 9.6463 (4) Å

b = 7.7062 (3) Å

c = 22.4675 (9) Å

β = 100.337 (2)°

V = 1643.04 (11) 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 ▶) T min = 0.980, T max = 0.990

17182 measured reflections

3692 independent reflections

2537 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.127

S = 1.02

3692 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812002711/bt5745sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002711/bt5745Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002711/bt5745Isup3.cml

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

C18H17NO4	F(000) = 656
Mr = 311.33	Dx = 1.259 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.6463 (4) Å	Cell parameters from 8725 reflections
b = 7.7062 (3) Å	θ = 2.8–29.1°
c = 22.4675 (9) Å	µ = 0.09 mm−1
β = 100.337 (2)°	T = 293 K
V = 1643.04 (11) Å3	Monoclinic, colourless
Z = 4	0.2 × 0.2 × 0.2 mm

Oxford Diffraction Xcalibur-S diffractometer	3692 independent reflections
Radiation source: fine-focus sealed tube	2537 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 15.9948 pixels mm-1	θmax = 27.3°, θmin = 2.2°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −9→9
Tmin = 0.980, Tmax = 0.990	l = −18→29
17182 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0557P)2 + 0.3308P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3692 reflections	Δρmax = 0.21 e Å−3
211 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0173 (18)

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	0.00948 (17)	0.7108 (2)	0.07286 (7)	0.0513 (4)
H1	0.0818	0.7020	0.1062	0.062*
C2	−0.09006 (15)	0.56814 (19)	0.05966 (6)	0.0444 (3)
C3	−0.20363 (17)	0.5708 (2)	0.01196 (7)	0.0583 (4)
H3	−0.2181	0.6677	−0.0130	0.070*
C4	−0.29464 (18)	0.4335 (3)	0.00100 (8)	0.0667 (5)
H4	−0.3711	0.4384	−0.0307	0.080*
C5	−0.27291 (18)	0.2889 (3)	0.03682 (8)	0.0626 (5)
H5	−0.3344	0.1953	0.0290	0.075*
C6	−0.16062 (18)	0.2804 (2)	0.08442 (8)	0.0566 (4)
H6	−0.1459	0.1815	0.1084	0.068*
C7	−0.07031 (15)	0.4206 (2)	0.09599 (6)	0.0449 (4)
C8	0.08136 (16)	0.2771 (2)	0.17851 (7)	0.0489 (4)
H8A	0.1178	0.1890	0.1546	0.059*
H8B	0.0014	0.2294	0.1937	0.059*
C9	0.19303 (15)	0.33459 (19)	0.22971 (7)	0.0447 (4)
C10	0.34042 (17)	0.3505 (2)	0.21965 (8)	0.0532 (4)
C11	0.4897 (2)	0.3269 (3)	0.14769 (11)	0.0870 (7)
H11A	0.5201	0.4455	0.1522	0.130*
H11B	0.4865	0.2909	0.1066	0.130*
H11C	0.5546	0.2546	0.1741	0.130*
C12	0.16887 (15)	0.37404 (19)	0.28457 (7)	0.0460 (4)
H12	0.2478	0.4040	0.3129	0.055*
C13	0.03513 (16)	0.3767 (2)	0.30627 (7)	0.0503 (4)
C14	−0.09178 (17)	0.4264 (3)	0.27074 (9)	0.0672 (5)
H14	−0.0935	0.4638	0.2313	0.081*
C15	−0.2148 (2)	0.4205 (3)	0.29358 (13)	0.0915 (8)
H15	−0.2995	0.4531	0.2695	0.110*
C16	−0.2125 (3)	0.3667 (3)	0.35192 (16)	0.1059 (9)
H16	−0.2963	0.3582	0.3668	0.127*
C17	−0.0873 (3)	0.3256 (3)	0.38844 (14)	0.1111 (9)
H17	−0.0856	0.2931	0.4284	0.133*
C18	0.0351 (2)	0.3325 (3)	0.36579 (10)	0.0784 (6)
H18	0.1201	0.3070	0.3910	0.094*
N1	0.00127 (14)	0.84521 (17)	0.04087 (6)	0.0510 (3)
O1	0.10817 (14)	0.96479 (16)	0.06224 (6)	0.0694 (4)
H1A	0.1018	1.0483	0.0393	0.104*
O2	0.04067 (12)	0.42920 (14)	0.14275 (5)	0.0603 (3)
O3	0.43880 (12)	0.3942 (2)	0.25704 (7)	0.0802 (4)
O4	0.35180 (13)	0.31127 (18)	0.16290 (6)	0.0711 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0566 (9)	0.0505 (9)	0.0424 (8)	−0.0007 (7)	−0.0024 (7)	0.0057 (7)
C2	0.0450 (8)	0.0486 (8)	0.0387 (7)	0.0017 (6)	0.0054 (6)	−0.0016 (6)
C3	0.0599 (10)	0.0615 (10)	0.0477 (9)	0.0048 (8)	−0.0056 (7)	0.0005 (8)
C4	0.0548 (10)	0.0810 (13)	0.0565 (10)	−0.0004 (9)	−0.0112 (8)	−0.0104 (9)
C5	0.0542 (10)	0.0704 (11)	0.0611 (11)	−0.0158 (8)	0.0046 (8)	−0.0129 (9)
C6	0.0598 (10)	0.0564 (10)	0.0524 (9)	−0.0108 (8)	0.0066 (8)	0.0012 (8)
C7	0.0429 (7)	0.0521 (9)	0.0388 (7)	−0.0026 (6)	0.0044 (6)	−0.0012 (6)
C8	0.0527 (9)	0.0446 (8)	0.0472 (8)	0.0008 (7)	0.0028 (7)	0.0060 (7)
C9	0.0425 (8)	0.0404 (8)	0.0496 (9)	0.0035 (6)	0.0038 (6)	0.0074 (6)
C10	0.0487 (9)	0.0499 (9)	0.0610 (10)	0.0058 (7)	0.0096 (8)	0.0053 (8)
C11	0.0764 (13)	0.0988 (16)	0.0972 (16)	0.0140 (12)	0.0463 (12)	0.0203 (13)
C12	0.0402 (7)	0.0468 (8)	0.0478 (8)	0.0013 (6)	−0.0009 (6)	0.0050 (7)
C13	0.0474 (8)	0.0473 (9)	0.0556 (9)	−0.0004 (7)	0.0074 (7)	0.0001 (7)
C14	0.0465 (9)	0.0818 (13)	0.0711 (12)	0.0038 (9)	0.0042 (8)	−0.0141 (10)
C15	0.0447 (10)	0.0960 (17)	0.134 (2)	−0.0010 (10)	0.0160 (12)	−0.0333 (16)
C16	0.0896 (18)	0.0783 (16)	0.172 (3)	−0.0038 (13)	0.0828 (19)	−0.0029 (17)
C17	0.123 (2)	0.1042 (19)	0.128 (2)	0.0311 (17)	0.0813 (19)	0.0423 (17)
C18	0.0792 (13)	0.0869 (14)	0.0748 (13)	0.0201 (11)	0.0293 (11)	0.0233 (11)
N1	0.0582 (8)	0.0473 (8)	0.0453 (7)	−0.0023 (6)	0.0031 (6)	0.0017 (6)
O1	0.0836 (9)	0.0544 (7)	0.0620 (8)	−0.0171 (6)	−0.0088 (6)	0.0092 (6)
O2	0.0628 (7)	0.0523 (7)	0.0563 (7)	−0.0121 (5)	−0.0151 (5)	0.0150 (5)
O3	0.0425 (7)	0.1103 (11)	0.0870 (9)	−0.0043 (7)	0.0093 (6)	−0.0138 (8)
O4	0.0638 (8)	0.0893 (9)	0.0651 (8)	0.0080 (7)	0.0243 (6)	0.0060 (7)

C1—N1	1.2553 (19)	C10—O4	1.334 (2)
C1—C2	1.455 (2)	C11—O4	1.437 (2)
C1—H1	0.9300	C11—H11A	0.9600
C2—C3	1.388 (2)	C11—H11B	0.9600
C2—C7	1.393 (2)	C11—H11C	0.9600
C3—C4	1.369 (2)	C12—C13	1.459 (2)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.369 (3)	C13—C18	1.380 (2)
C4—H4	0.9300	C13—C14	1.390 (2)
C5—C6	1.380 (2)	C14—C15	1.376 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.383 (2)	C15—C16	1.371 (4)
C6—H6	0.9300	C15—H15	0.9300
C7—O2	1.3604 (17)	C16—C17	1.370 (4)
C8—O2	1.4356 (17)	C16—H16	0.9300
C8—C9	1.495 (2)	C17—C18	1.368 (3)
C8—H8A	0.9700	C17—H17	0.9300
C8—H8B	0.9700	C18—H18	0.9300
C9—C12	1.330 (2)	N1—O1	1.4019 (17)
C9—C10	1.484 (2)	O1—H1A	0.8200
C10—O3	1.1976 (19)
N1—C1—C2	122.37 (14)	O4—C10—C9	111.86 (14)
N1—C1—H1	118.8	O4—C11—H11A	109.5
C2—C1—H1	118.8	O4—C11—H11B	109.5
C3—C2—C7	118.05 (14)	H11A—C11—H11B	109.5
C3—C2—C1	123.16 (14)	O4—C11—H11C	109.5
C7—C2—C1	118.78 (12)	H11A—C11—H11C	109.5
C4—C3—C2	121.30 (16)	H11B—C11—H11C	109.5
C4—C3—H3	119.4	C9—C12—C13	128.71 (14)
C2—C3—H3	119.4	C9—C12—H12	115.6
C5—C4—C3	119.87 (15)	C13—C12—H12	115.6
C5—C4—H4	120.1	C18—C13—C14	118.13 (17)
C3—C4—H4	120.1	C18—C13—C12	118.30 (15)
C4—C5—C6	120.67 (16)	C14—C13—C12	123.54 (15)
C4—C5—H5	119.7	C15—C14—C13	120.4 (2)
C6—C5—H5	119.7	C15—C14—H14	119.8
C5—C6—C7	119.28 (16)	C13—C14—H14	119.8
C5—C6—H6	120.4	C16—C15—C14	119.9 (2)
C7—C6—H6	120.4	C16—C15—H15	120.0
O2—C7—C6	124.41 (14)	C14—C15—H15	120.0
O2—C7—C2	114.76 (13)	C17—C16—C15	120.3 (2)
C6—C7—C2	120.82 (13)	C17—C16—H16	119.9
O2—C8—C9	105.98 (12)	C15—C16—H16	119.9
O2—C8—H8A	110.5	C18—C17—C16	119.7 (2)
C9—C8—H8A	110.5	C18—C17—H17	120.2
O2—C8—H8B	110.5	C16—C17—H17	120.2
C9—C8—H8B	110.5	C17—C18—C13	121.3 (2)
H8A—C8—H8B	108.7	C17—C18—H18	119.3
C12—C9—C10	117.02 (14)	C13—C18—H18	119.3
C12—C9—C8	123.97 (14)	C1—N1—O1	112.30 (12)
C10—C9—C8	119.01 (14)	N1—O1—H1A	109.5
O3—C10—O4	122.93 (16)	C7—O2—C8	119.38 (12)
O3—C10—C9	125.20 (16)	C10—O4—C11	116.56 (16)
N1—C1—C2—C3	−1.8 (3)	C10—C9—C12—C13	177.38 (14)
N1—C1—C2—C7	177.49 (15)	C8—C9—C12—C13	−2.3 (2)
C7—C2—C3—C4	0.5 (2)	C9—C12—C13—C18	146.92 (19)
C1—C2—C3—C4	179.80 (17)	C9—C12—C13—C14	−35.1 (3)
C2—C3—C4—C5	−1.1 (3)	C18—C13—C14—C15	−4.1 (3)
C3—C4—C5—C6	0.6 (3)	C12—C13—C14—C15	177.96 (17)
C4—C5—C6—C7	0.5 (3)	C13—C14—C15—C16	0.5 (3)
C5—C6—C7—O2	177.67 (16)	C14—C15—C16—C17	2.7 (4)
C5—C6—C7—C2	−1.1 (3)	C15—C16—C17—C18	−2.3 (4)
C3—C2—C7—O2	−178.30 (14)	C16—C17—C18—C13	−1.4 (4)
C1—C2—C7—O2	2.4 (2)	C14—C13—C18—C17	4.6 (3)
C3—C2—C7—C6	0.6 (2)	C12—C13—C18—C17	−177.4 (2)
C1—C2—C7—C6	−178.70 (15)	C2—C1—N1—O1	179.94 (14)
O2—C8—C9—C12	97.38 (17)	C6—C7—O2—C8	8.8 (2)
O2—C8—C9—C10	−82.28 (16)	C2—C7—O2—C8	−172.33 (14)
C12—C9—C10—O3	0.7 (2)	C9—C8—O2—C7	−173.35 (13)
C8—C9—C10—O3	−179.59 (16)	O3—C10—O4—C11	−1.1 (3)
C12—C9—C10—O4	−178.71 (14)	C9—C10—O4—C11	178.38 (15)
C8—C9—C10—O4	1.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1i	0.82	2.06	2.7836 (19)	146
C15—H15···O3ii	0.93	2.53	3.300 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1i	0.82	2.06	2.7836 (19)	146
C15—H15⋯O3ii	0.93	2.53	3.300 (2)	140

Symmetry codes: (i) ; (ii) .