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

In the title compound, C(18)H(16)ClNO(4), the dihedral angle between the mean planes through the aromatic rings is 83.8 (8)°. The hy-droxy-ethanimine group is essentially coplanar with the ring to which it is attached [O-N-C-C torsion angle = -177.96 (13)°]. The mol-ecules are linked into centrosymmetric R(2) (2)(6) dimers via O-H⋯N hydrogen bonds. The crystal packing is further stabilized by C-H⋯O inter-actions.

Related literature

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 ▶). For the use of oxime ligands in coordination chemistry, see: Chaudhuri (2003 ▶). For related structures, see: Wang et al. (2011 ▶); Govindan et al. (2011 ▶).

Experimental

Crystal data

C18H16ClNO4

M = 345.77

Triclinic,

a = 8.8860 (4) Å

b = 9.3428 (5) Å

c = 12.1494 (6) Å

α = 72.289 (3)°

β = 74.319 (2)°

γ = 63.429 (2)°

V = 848.63 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.25 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

22640 measured reflections

6056 independent reflections

4013 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.161

S = 1.04

6056 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.51 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811038372/bt5635sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038372/bt5635Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811038372/bt5635Isup3.cml

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

C18H16ClNO4	Z = 2
Mr = 345.77	F(000) = 360
Triclinic, P1	Dx = 1.353 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8860 (4) Å	Cell parameters from 6056 reflections
b = 9.3428 (5) Å	θ = 2.5–32.5°
c = 12.1494 (6) Å	µ = 0.25 mm−1
α = 72.289 (3)°	T = 293 K
β = 74.319 (2)°	Block, white crystalline
γ = 63.429 (2)°	0.25 × 0.22 × 0.19 mm
V = 848.63 (7) Å3

Bruker APEXII CCD area-detector diffractometer	6056 independent reflections
Radiation source: fine-focus sealed tube	4013 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω and φ scans	θmax = 32.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.978, Tmax = 0.983	k = −13→14
22640 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0713P)2 + 0.1584P] where P = (Fo2 + 2Fc2)/3
6056 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.51 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
C3	0.76040 (18)	0.46783 (19)	0.49605 (13)	0.0517 (3)
H3	0.8399	0.4114	0.4401	0.062*
C4	0.7342 (2)	0.6270 (2)	0.48827 (14)	0.0592 (4)
H4	0.7965	0.6772	0.4281	0.071*
C5	0.6153 (2)	0.71133 (19)	0.57003 (15)	0.0567 (4)
H5	0.5972	0.8191	0.5646	0.068*
C6	0.52179 (19)	0.63806 (17)	0.66070 (13)	0.0487 (3)
H6	0.4415	0.6963	0.7155	0.058*
C7	0.54922 (15)	0.47730 (15)	0.66875 (11)	0.0384 (3)
C2	0.67024 (15)	0.38967 (16)	0.58609 (11)	0.0396 (3)
C1	0.69450 (17)	0.22183 (17)	0.59516 (12)	0.0457 (3)
H1	0.6076	0.1872	0.6359	0.055*
C9	0.25890 (16)	0.35977 (17)	0.91804 (11)	0.0423 (3)
C12	0.31776 (17)	0.23354 (17)	1.00615 (12)	0.0456 (3)
H12	0.2466	0.1781	1.0421	0.055*
C13	0.47403 (17)	0.16776 (16)	1.05564 (12)	0.0441 (3)
C14	0.62373 (18)	0.18941 (19)	0.99839 (13)	0.0521 (3)
H14	0.6292	0.2485	0.9215	0.062*
C15	0.7634 (2)	0.1246 (2)	1.05398 (15)	0.0576 (4)
H15	0.8618	0.1414	1.0152	0.069*
C16	0.7569 (2)	0.03523 (19)	1.16672 (14)	0.0548 (3)
C17	0.6130 (2)	0.0072 (2)	1.22484 (15)	0.0609 (4)
H17	0.6102	−0.0555	1.3007	0.073*
C18	0.4742 (2)	0.07297 (19)	1.16918 (14)	0.0548 (4)
H18	0.3772	0.0539	1.2083	0.066*
C11	−0.1064 (2)	0.5320 (3)	0.76182 (19)	0.0834 (6)
H11A	−0.0975	0.4408	0.7358	0.125*
H11B	−0.1339	0.6279	0.6999	0.125*
H11C	−0.1945	0.5510	0.8285	0.125*
C10	0.09091 (18)	0.38980 (19)	0.89357 (13)	0.0497 (3)
N1	0.83143 (16)	0.12225 (15)	0.54872 (12)	0.0522 (3)
O1	0.82593 (17)	−0.03007 (15)	0.56443 (13)	0.0761 (4)
H1A	0.9160	−0.0912	0.5328	0.114*
O2	0.46629 (12)	0.39236 (12)	0.75426 (8)	0.0464 (2)
O3	−0.00369 (16)	0.32873 (18)	0.95683 (13)	0.0781 (4)
O4	0.05387 (15)	0.49645 (18)	0.79367 (11)	0.0693 (3)
Cl1	0.93049 (7)	−0.04275 (8)	1.23850 (5)	0.0881 (2)
C8	0.34517 (17)	0.47105 (16)	0.84520 (12)	0.0437 (3)
H8A	0.2621	0.5754	0.8114	0.052*
H8B	0.4027	0.4906	0.8930	0.052*

	U11	U22	U33	U12	U13	U23
C3	0.0464 (7)	0.0539 (8)	0.0416 (7)	−0.0187 (6)	0.0038 (5)	−0.0038 (6)
C4	0.0572 (8)	0.0555 (9)	0.0522 (8)	−0.0278 (7)	−0.0007 (6)	0.0071 (7)
C5	0.0596 (9)	0.0437 (7)	0.0613 (9)	−0.0233 (7)	−0.0090 (7)	−0.0001 (7)
C6	0.0489 (7)	0.0441 (7)	0.0495 (7)	−0.0176 (6)	−0.0034 (6)	−0.0102 (6)
C7	0.0359 (5)	0.0420 (6)	0.0344 (6)	−0.0160 (5)	−0.0038 (4)	−0.0048 (5)
C2	0.0347 (5)	0.0439 (6)	0.0351 (6)	−0.0142 (5)	−0.0031 (4)	−0.0055 (5)
C1	0.0420 (6)	0.0501 (7)	0.0413 (7)	−0.0204 (6)	0.0056 (5)	−0.0121 (5)
C9	0.0374 (6)	0.0465 (7)	0.0415 (6)	−0.0168 (5)	0.0063 (5)	−0.0182 (5)
C12	0.0432 (6)	0.0468 (7)	0.0458 (7)	−0.0213 (6)	0.0054 (5)	−0.0140 (6)
C13	0.0448 (6)	0.0402 (6)	0.0443 (7)	−0.0177 (5)	0.0023 (5)	−0.0116 (5)
C14	0.0469 (7)	0.0557 (8)	0.0457 (7)	−0.0224 (6)	0.0011 (6)	−0.0046 (6)
C15	0.0478 (8)	0.0616 (9)	0.0604 (9)	−0.0251 (7)	−0.0023 (6)	−0.0090 (7)
C16	0.0557 (8)	0.0506 (8)	0.0561 (9)	−0.0166 (7)	−0.0114 (6)	−0.0133 (7)
C17	0.0661 (10)	0.0559 (9)	0.0491 (8)	−0.0220 (8)	−0.0062 (7)	−0.0015 (7)
C18	0.0549 (8)	0.0492 (8)	0.0524 (8)	−0.0245 (7)	0.0010 (6)	−0.0026 (6)
C11	0.0504 (9)	0.1214 (18)	0.0703 (12)	−0.0190 (10)	−0.0147 (8)	−0.0288 (12)
C10	0.0424 (7)	0.0541 (8)	0.0506 (8)	−0.0168 (6)	0.0015 (5)	−0.0199 (6)
N1	0.0478 (6)	0.0478 (6)	0.0575 (7)	−0.0212 (5)	0.0089 (5)	−0.0180 (5)
O1	0.0708 (8)	0.0564 (7)	0.0973 (10)	−0.0341 (6)	0.0298 (7)	−0.0353 (7)
O2	0.0487 (5)	0.0448 (5)	0.0412 (5)	−0.0218 (4)	0.0115 (4)	−0.0145 (4)
O3	0.0571 (7)	0.0865 (9)	0.0933 (10)	−0.0428 (7)	−0.0108 (6)	−0.0013 (7)
O4	0.0495 (6)	0.1007 (10)	0.0502 (6)	−0.0280 (6)	−0.0061 (5)	−0.0105 (6)
Cl1	0.0749 (3)	0.1059 (4)	0.0811 (4)	−0.0278 (3)	−0.0320 (3)	−0.0120 (3)
C8	0.0416 (6)	0.0430 (6)	0.0425 (7)	−0.0160 (5)	0.0050 (5)	−0.0154 (5)

C3—C4	1.375 (2)	C14—C15	1.377 (2)
C3—C2	1.3911 (18)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.372 (2)
C4—C5	1.374 (2)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.379 (2)
C5—C6	1.389 (2)	C16—Cl1	1.7336 (17)
C5—H5	0.9300	C17—C18	1.370 (2)
C6—C7	1.3859 (19)	C17—H17	0.9300
C6—H6	0.9300	C18—H18	0.9300
C7—O2	1.3637 (14)	C11—O4	1.444 (2)
C7—C2	1.4015 (17)	C11—H11A	0.9600
C2—C1	1.4570 (19)	C11—H11B	0.9600
C1—N1	1.2649 (17)	C11—H11C	0.9600
C1—H1	0.9300	C10—O3	1.1982 (19)
C9—C12	1.339 (2)	C10—O4	1.327 (2)
C9—C10	1.487 (2)	N1—O1	1.3985 (16)
C9—C8	1.4961 (18)	O1—H1A	0.8200
C12—C13	1.460 (2)	O2—C8	1.4364 (14)
C12—H12	0.9300	C8—H8A	0.9700
C13—C18	1.394 (2)	C8—H8B	0.9700
C13—C14	1.3960 (19)
C4—C3—C2	121.24 (13)	C13—C14—H14	119.5
C4—C3—H3	119.4	C16—C15—C14	119.71 (14)
C2—C3—H3	119.4	C16—C15—H15	120.1
C5—C4—C3	119.48 (13)	C14—C15—H15	120.1
C5—C4—H4	120.3	C15—C16—C17	120.90 (15)
C3—C4—H4	120.3	C15—C16—Cl1	120.00 (13)
C4—C5—C6	121.02 (14)	C17—C16—Cl1	119.11 (13)
C4—C5—H5	119.5	C18—C17—C16	119.01 (15)
C6—C5—H5	119.5	C18—C17—H17	120.5
C7—C6—C5	119.37 (13)	C16—C17—H17	120.5
C7—C6—H6	120.3	C17—C18—C13	121.93 (14)
C5—C6—H6	120.3	C17—C18—H18	119.0
O2—C7—C6	124.59 (12)	C13—C18—H18	119.0
O2—C7—C2	115.15 (11)	O4—C11—H11A	109.5
C6—C7—C2	120.25 (12)	O4—C11—H11B	109.5
C3—C2—C7	118.63 (12)	H11A—C11—H11B	109.5
C3—C2—C1	122.13 (12)	O4—C11—H11C	109.5
C7—C2—C1	119.22 (11)	H11A—C11—H11C	109.5
N1—C1—C2	121.29 (12)	H11B—C11—H11C	109.5
N1—C1—H1	119.4	O3—C10—O4	122.92 (15)
C2—C1—H1	119.4	O3—C10—C9	124.79 (15)
C12—C9—C10	115.36 (12)	O4—C10—C9	112.26 (13)
C12—C9—C8	126.12 (13)	C1—N1—O1	112.01 (12)
C10—C9—C8	118.52 (13)	N1—O1—H1A	109.5
C9—C12—C13	131.27 (12)	C7—O2—C8	118.70 (10)
C9—C12—H12	114.4	C10—O4—C11	116.24 (15)
C13—C12—H12	114.4	O2—C8—C9	107.58 (10)
C18—C13—C14	117.39 (14)	O2—C8—H8A	110.2
C18—C13—C12	116.98 (12)	C9—C8—H8A	110.2
C14—C13—C12	125.62 (13)	O2—C8—H8B	110.2
C15—C14—C13	121.01 (14)	C9—C8—H8B	110.2
C15—C14—H14	119.5	H8A—C8—H8B	108.5
C2—C3—C4—C5	−0.8 (3)	C14—C15—C16—C17	1.0 (3)
C3—C4—C5—C6	0.3 (3)	C14—C15—C16—Cl1	−178.50 (13)
C4—C5—C6—C7	0.1 (2)	C15—C16—C17—C18	−1.4 (3)
C5—C6—C7—O2	179.42 (13)	Cl1—C16—C17—C18	178.09 (13)
C5—C6—C7—C2	0.0 (2)	C16—C17—C18—C13	−0.2 (3)
C4—C3—C2—C7	0.9 (2)	C14—C13—C18—C17	2.0 (2)
C4—C3—C2—C1	179.24 (14)	C12—C13—C18—C17	−179.02 (14)
O2—C7—C2—C3	−179.96 (12)	C12—C9—C10—O3	12.6 (2)
C6—C7—C2—C3	−0.48 (19)	C8—C9—C10—O3	−166.71 (15)
O2—C7—C2—C1	1.66 (17)	C12—C9—C10—O4	−168.91 (13)
C6—C7—C2—C1	−178.86 (13)	C8—C9—C10—O4	11.76 (17)
C3—C2—C1—N1	23.8 (2)	C2—C1—N1—O1	−177.96 (13)
C7—C2—C1—N1	−157.87 (14)	C6—C7—O2—C8	−1.97 (19)
C10—C9—C12—C13	−179.66 (13)	C2—C7—O2—C8	177.48 (11)
C8—C9—C12—C13	−0.4 (2)	O3—C10—O4—C11	−2.2 (2)
C9—C12—C13—C18	158.99 (15)	C9—C10—O4—C11	179.32 (14)
C9—C12—C13—C14	−22.1 (2)	C7—O2—C8—C9	173.33 (11)
C18—C13—C14—C15	−2.4 (2)	C12—C9—C8—O2	83.72 (16)
C12—C13—C14—C15	178.71 (14)	C10—C9—C8—O2	−97.03 (13)
C13—C14—C15—C16	1.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1i	0.82	2.12	2.8309 (16)	145.
C15—H15···O3ii	0.93	2.38	3.186 (2)	145.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1i	0.82	2.12	2.8309 (16)	145
C15—H15⋯O3ii	0.93	2.38	3.186 (2)	145

Symmetry codes: (i) ; (ii) .