Methyl (E)-3-(2-formyl-phen-oxy)acrylate.

In the title compound, C11H10O4, the methyl acrylate sub-stituent adopts an extended E conformation with all torsion angles close to 180°. The conformation of the keto group with respect to the olefinic double bond is typically S-trans. In the crystal, mol-ecules are linked via pairs of C-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(8) graph-set motif. The dimers are further linked via C-H⋯O hydrogen bonds, forming chains along [001], which enclose R 3 (2)(16) graph-set ring motifs. The keto group O atomaccepts two C-H⋯O interactions.

Related literature

For applications of acrylate derivatives, see: Xiao et al. (2008 ▶); De et al. (2011 ▶); Sharma (2011 ▶). For related crystal structures, see: Karthikeyan et al. (2012 ▶). For E-conformation aspects, see: Dunitz & Schweizer (1982 ▶). For resonance effects of acrylate, see: Merlino (1971 ▶); Varghese et al. (1986 ▶). For graph-set motif notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H10O4

M = 206.19

Monoclinic,

a = 17.7458 (8) Å

b = 4.0629 (2) Å

c = 14.5745 (7) Å

β = 107.868 (3)°

V = 1000.13 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer

13052 measured reflections

2015 independent reflections

1523 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.155

S = 1.06

2015 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814010617/su2732sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010617/su2732Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814010617/su2732Isup3.cml

CCDC reference: 1001914

Additional supporting information: crystallographic information; 3D view; checkCIF report

C11H10O4	F(000) = 432
Mr = 206.19	Dx = 1.369 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybc	Cell parameters from 2015 reflections
a = 17.7458 (8) Å	θ = 1.2–26.3°
b = 4.0629 (2) Å	µ = 0.11 mm−1
c = 14.5745 (7) Å	T = 293 K
β = 107.868 (3)°	Block, colorless
V = 1000.13 (8) Å3	0.20 × 0.15 × 0.10 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	1523 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 26.3°, θmin = 1.2°
ω scans	h = −22→21
13052 measured reflections	k = −5→5
2015 independent 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.1001P)2 + 0.0957P] where P = (Fo2 + 2Fc2)/3
2015 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.17 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	0.19462 (11)	0.6483 (5)	1.09554 (11)	0.0570 (5)
H1	0.2426	0.7588	1.1079	0.068*
C2	0.16126 (8)	0.4928 (4)	1.00055 (10)	0.0437 (4)
C3	0.08802 (9)	0.3378 (4)	0.97865 (12)	0.0518 (5)
H3	0.0621	0.3250	1.0252	0.062*
C4	0.05341 (10)	0.2034 (5)	0.88901 (13)	0.0574 (5)
H4	0.0040	0.1033	0.8746	0.069*
C5	0.09250 (10)	0.2182 (5)	0.82056 (12)	0.0545 (5)
H5	0.0692	0.1265	0.7600	0.065*
C6	0.16554 (9)	0.3671 (4)	0.84083 (11)	0.0484 (4)
H6	0.1918	0.3734	0.7946	0.058*
C7	0.19943 (8)	0.5068 (4)	0.93033 (10)	0.0425 (4)
C8	0.30241 (9)	0.7868 (4)	0.88985 (11)	0.0463 (4)
H8	0.2706	0.8014	0.8260	0.056*
C9	0.37579 (9)	0.8937 (5)	0.91462 (12)	0.0542 (5)
H9	0.4075	0.8649	0.9780	0.065*
C10	0.40974 (9)	1.0549 (5)	0.84737 (12)	0.0516 (4)
C11	0.39059 (12)	1.2299 (6)	0.68764 (14)	0.0655 (5)
H11A	0.4103	1.4452	0.7097	0.098*
H11B	0.3494	1.2484	0.6272	0.098*
H11C	0.4329	1.0976	0.6794	0.098*
O1	0.35946 (7)	1.0781 (3)	0.75754 (8)	0.0598 (4)
O2	0.47632 (7)	1.1596 (4)	0.86851 (10)	0.0723 (5)
O3	0.27287 (6)	0.6544 (3)	0.95771 (7)	0.0541 (4)
O4	0.16367 (9)	0.6413 (5)	1.15808 (9)	0.0821 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0536 (10)	0.0738 (13)	0.0448 (8)	0.0075 (8)	0.0171 (7)	0.0039 (8)
C2	0.0403 (8)	0.0498 (10)	0.0419 (8)	0.0095 (6)	0.0142 (6)	0.0084 (7)
C3	0.0432 (9)	0.0604 (11)	0.0562 (9)	0.0071 (7)	0.0220 (7)	0.0119 (8)
C4	0.0442 (9)	0.0590 (11)	0.0665 (11)	−0.0046 (8)	0.0134 (8)	0.0077 (8)
C5	0.0531 (10)	0.0542 (10)	0.0504 (9)	0.0009 (8)	0.0074 (7)	0.0007 (8)
C6	0.0485 (9)	0.0547 (10)	0.0443 (8)	0.0048 (7)	0.0175 (7)	0.0049 (7)
C7	0.0357 (7)	0.0485 (10)	0.0429 (7)	0.0054 (6)	0.0115 (6)	0.0082 (6)
C8	0.0411 (8)	0.0565 (10)	0.0435 (8)	0.0025 (7)	0.0162 (6)	0.0013 (7)
C9	0.0425 (8)	0.0710 (12)	0.0490 (9)	−0.0019 (8)	0.0137 (7)	−0.0027 (8)
C10	0.0383 (8)	0.0609 (11)	0.0580 (9)	−0.0018 (7)	0.0184 (7)	−0.0063 (8)
C11	0.0639 (11)	0.0721 (13)	0.0669 (11)	−0.0039 (10)	0.0297 (9)	0.0095 (10)
O1	0.0487 (7)	0.0767 (9)	0.0553 (7)	−0.0123 (6)	0.0181 (5)	0.0033 (6)
O2	0.0431 (7)	0.1021 (13)	0.0731 (8)	−0.0180 (7)	0.0197 (6)	−0.0050 (7)
O3	0.0403 (6)	0.0800 (9)	0.0427 (6)	−0.0071 (5)	0.0139 (5)	0.0042 (5)
O4	0.0787 (10)	0.1250 (15)	0.0509 (7)	−0.0008 (9)	0.0322 (7)	−0.0084 (7)

C1—O4	1.200 (2)	C7—O3	1.3778 (18)
C1—C2	1.471 (2)	C8—C9	1.314 (2)
C1—H1	0.9300	C8—O3	1.3640 (18)
C2—C3	1.390 (2)	C8—H8	0.9300
C2—C7	1.3910 (19)	C9—C10	1.454 (2)
C3—C4	1.375 (3)	C9—H9	0.9300
C3—H3	0.9300	C10—O2	1.2035 (19)
C4—C5	1.380 (2)	C10—O1	1.342 (2)
C4—H4	0.9300	C11—O1	1.438 (2)
C5—C6	1.378 (2)	C11—H11A	0.9600
C5—H5	0.9300	C11—H11B	0.9600
C6—C7	1.380 (2)	C11—H11C	0.9600
C6—H6	0.9300
O4—C1—C2	123.98 (17)	O3—C7—C2	115.83 (13)
O4—C1—H1	118.0	C6—C7—C2	120.61 (14)
C2—C1—H1	118.0	C9—C8—O3	120.00 (14)
C3—C2—C7	118.80 (14)	C9—C8—H8	120.0
C3—C2—C1	119.24 (14)	O3—C8—H8	120.0
C7—C2—C1	121.91 (15)	C8—C9—C10	122.98 (15)
C4—C3—C2	120.77 (15)	C8—C9—H9	118.5
C4—C3—H3	119.6	C10—C9—H9	118.5
C2—C3—H3	119.6	O2—C10—O1	122.10 (15)
C3—C4—C5	119.52 (16)	O2—C10—C9	124.32 (16)
C3—C4—H4	120.2	O1—C10—C9	113.58 (14)
C5—C4—H4	120.2	O1—C11—H11A	109.5
C6—C5—C4	120.83 (15)	O1—C11—H11B	109.5
C6—C5—H5	119.6	H11A—C11—H11B	109.5
C4—C5—H5	119.6	O1—C11—H11C	109.5
C5—C6—C7	119.46 (15)	H11A—C11—H11C	109.5
C5—C6—H6	120.3	H11B—C11—H11C	109.5
C7—C6—H6	120.3	C10—O1—C11	115.85 (13)
O3—C7—C6	123.51 (13)	C8—O3—C7	120.10 (12)
O4—C1—C2—C3	2.7 (3)	C3—C2—C7—C6	−0.5 (2)
O4—C1—C2—C7	−179.85 (17)	C1—C2—C7—C6	−178.03 (15)
C7—C2—C3—C4	−0.6 (2)	O3—C8—C9—C10	−176.28 (16)
C1—C2—C3—C4	176.94 (17)	C8—C9—C10—O2	178.78 (19)
C2—C3—C4—C5	1.0 (3)	C8—C9—C10—O1	−1.2 (3)
C3—C4—C5—C6	−0.3 (3)	O2—C10—O1—C11	1.2 (3)
C4—C5—C6—C7	−0.9 (3)	C9—C10—O1—C11	−178.82 (16)
C5—C6—C7—O3	178.55 (15)	C9—C8—O3—C7	−172.25 (16)
C5—C6—C7—C2	1.3 (2)	C6—C7—O3—C8	26.2 (2)
C3—C2—C7—O3	−178.02 (14)	C2—C7—O3—C8	−156.37 (14)
C1—C2—C7—O3	4.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2i	0.93	2.54	3.440 (2)	164
C8—H8···O4ii	0.93	2.61	3.529 (2)	171
C11—H11C···O2iii	0.96	2.63	3.578 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O2i	0.93	2.54	3.440 (2)	164
C8—H8⋯O4ii	0.93	2.61	3.529 (2)	171
C11—H11C⋯O2iii	0.96	2.63	3.578 (2)	168

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