2-Formyl-6-meth-oxy-phenyl cinnamate.

In the title compound, C(17)H(14)O(4), the C=C bond adopts an E conformation and the dihedral angle between the benzene rings is 73.9 (1)°. The crystal packing features C-H⋯O hydrogen bonds, which generate C(4) chains propagating along the b-axis direction. Weak aromatic π-π stacking inter-actions [centroid-centroid distance = 3.703 (1) Å] are also observed.

Related literature

For the biological properties of cinnamate derivatives, see: Sharma (2011 ▶). For related structures, see: Kaitner & Stilinović (2007 ▶); Anuradha et al. (2012 ▶).

Experimental

Crystal data

C17H14O4

M = 282.28

Orthorhombic,

a = 10.7908 (7) Å

b = 10.4672 (5) Å

c = 25.8714 (17) Å

V = 2922.2 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.23 × 0.21 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.910, T max = 0.941

14344 measured reflections

2665 independent reflections

1909 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.106

S = 1.01

2665 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.12 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); 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/S160053681202747X/hb6858sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202747X/hb6858Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202747X/hb6858Isup3.cml

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

C17H14O4	F(000) = 1184
Mr = 282.28	Dx = 1.283 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2879 reflections
a = 10.7908 (7) Å	θ = 1.0–1.0°
b = 10.4672 (5) Å	µ = 0.09 mm−1
c = 25.8714 (17) Å	T = 293 K
V = 2922.2 (3) Å3	Block, colourless
Z = 8	0.23 × 0.21 × 0.15 mm

Bruker APEXII CCD diffractometer	2665 independent reflections
Radiation source: fine-focus sealed tube	1909 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 10.0 pixels mm-1	θmax = 26.0°, θmin = 2.5°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→11
Tmin = 0.910, Tmax = 0.941	l = −31→31
14344 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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0446P)2 + 0.7231P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
2665 reflections	Δρmax = 0.15 e Å−3
192 parameters	Δρmin = −0.12 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: 0.0020 (5)

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	0.62871 (15)	−0.06915 (15)	0.54858 (6)	0.0487 (4)
C2	0.54050 (16)	−0.15242 (16)	0.56771 (7)	0.0552 (4)
C3	0.48566 (18)	−0.23727 (18)	0.53357 (8)	0.0686 (5)
H3	0.4252	−0.2935	0.5453	0.082*
C4	0.5205 (2)	−0.2388 (2)	0.48191 (8)	0.0732 (6)
H4	0.4827	−0.2959	0.4593	0.088*
C5	0.60927 (19)	−0.15776 (18)	0.46393 (7)	0.0649 (5)
H5	0.6326	−0.1603	0.4293	0.078*
C6	0.66465 (16)	−0.07149 (16)	0.49726 (7)	0.0532 (4)
C7	0.7586 (2)	0.0175 (2)	0.47767 (8)	0.0702 (5)
H7	0.7865	0.0813	0.4998	0.084*
C8	0.76334 (15)	−0.01222 (16)	0.61648 (6)	0.0459 (4)
C9	0.78497 (15)	0.08922 (16)	0.65399 (6)	0.0491 (4)
H9	0.7521	0.1700	0.6480	0.059*
C10	0.85036 (15)	0.06857 (17)	0.69633 (6)	0.0509 (4)
H10	0.8863	−0.0119	0.6993	0.061*
C11	0.87318 (14)	0.15626 (16)	0.73902 (6)	0.0484 (4)
C12	0.82650 (17)	0.28000 (17)	0.73974 (6)	0.0595 (5)
H12	0.7812	0.3101	0.7117	0.071*
C13	0.84677 (18)	0.35820 (19)	0.78160 (7)	0.0663 (5)
H13	0.8149	0.4407	0.7816	0.080*
C14	0.91335 (17)	0.3161 (2)	0.82338 (7)	0.0667 (5)
H14	0.9258	0.3694	0.8517	0.080*
C15	0.96137 (18)	0.1953 (2)	0.82313 (7)	0.0703 (6)
H15	1.0074	0.1665	0.8512	0.084*
C16	0.94166 (17)	0.11608 (19)	0.78136 (6)	0.0619 (5)
H16	0.9749	0.0341	0.7816	0.074*
C17	0.41618 (19)	−0.2177 (2)	0.63873 (9)	0.0923 (7)
H17A	0.3401	−0.1947	0.6219	0.138*
H17B	0.4085	−0.2032	0.6752	0.138*
H17C	0.4336	−0.3063	0.6325	0.138*
O1	0.80202 (17)	0.01350 (16)	0.43495 (6)	0.0987 (5)
O2	0.67581 (11)	0.02494 (10)	0.58150 (4)	0.0542 (3)
O3	0.81108 (12)	−0.11529 (12)	0.61497 (5)	0.0630 (4)
O4	0.51428 (13)	−0.14196 (13)	0.61881 (5)	0.0731 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0519 (10)	0.0386 (10)	0.0557 (9)	0.0070 (7)	−0.0156 (8)	−0.0053 (7)
C2	0.0530 (10)	0.0508 (11)	0.0617 (10)	0.0072 (8)	−0.0079 (8)	−0.0057 (8)
C3	0.0582 (11)	0.0561 (12)	0.0914 (15)	−0.0041 (9)	−0.0122 (10)	−0.0078 (10)
C4	0.0754 (13)	0.0635 (14)	0.0806 (14)	0.0058 (11)	−0.0266 (11)	−0.0246 (11)
C5	0.0766 (13)	0.0622 (13)	0.0560 (10)	0.0125 (11)	−0.0150 (10)	−0.0123 (9)
C6	0.0599 (11)	0.0471 (11)	0.0527 (9)	0.0099 (8)	−0.0109 (8)	−0.0010 (8)
C7	0.0815 (14)	0.0650 (14)	0.0641 (11)	0.0035 (11)	−0.0039 (11)	0.0060 (10)
C8	0.0482 (9)	0.0427 (11)	0.0468 (8)	−0.0014 (8)	−0.0038 (7)	0.0034 (7)
C9	0.0550 (10)	0.0404 (10)	0.0520 (9)	−0.0011 (8)	−0.0064 (8)	−0.0009 (7)
C10	0.0528 (10)	0.0467 (11)	0.0531 (9)	0.0010 (8)	−0.0034 (8)	0.0018 (7)
C11	0.0483 (9)	0.0520 (11)	0.0449 (8)	−0.0040 (8)	−0.0014 (7)	0.0005 (7)
C12	0.0710 (12)	0.0564 (12)	0.0510 (10)	−0.0017 (9)	−0.0106 (9)	−0.0022 (8)
C13	0.0793 (13)	0.0588 (12)	0.0607 (11)	−0.0032 (10)	−0.0011 (10)	−0.0107 (9)
C14	0.0587 (11)	0.0911 (16)	0.0502 (10)	−0.0126 (11)	0.0015 (9)	−0.0172 (10)
C15	0.0601 (11)	0.1040 (17)	0.0469 (9)	0.0032 (11)	−0.0090 (8)	−0.0033 (10)
C16	0.0625 (11)	0.0700 (13)	0.0532 (10)	0.0090 (9)	−0.0073 (9)	0.0018 (9)
C17	0.0650 (13)	0.118 (2)	0.0936 (16)	−0.0043 (13)	0.0096 (12)	0.0217 (14)
O1	0.1247 (14)	0.0973 (12)	0.0741 (10)	−0.0031 (10)	0.0230 (9)	0.0072 (8)
O2	0.0664 (7)	0.0407 (7)	0.0556 (6)	0.0052 (5)	−0.0191 (6)	−0.0055 (5)
O3	0.0680 (8)	0.0495 (8)	0.0717 (8)	0.0140 (6)	−0.0187 (6)	−0.0094 (6)
O4	0.0713 (9)	0.0803 (10)	0.0678 (8)	−0.0064 (7)	0.0058 (7)	−0.0038 (7)

C1—C2	1.382 (2)	C9—H9	0.9300
C1—C6	1.383 (2)	C10—C11	1.457 (2)
C1—O2	1.3978 (19)	C10—H10	0.9300
C2—O4	1.356 (2)	C11—C16	1.387 (2)
C2—C3	1.385 (2)	C11—C12	1.390 (2)
C3—C4	1.389 (3)	C12—C13	1.375 (2)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.361 (3)	C13—C14	1.371 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.384 (2)	C14—C15	1.366 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.468 (3)	C15—C16	1.379 (3)
C7—O1	1.201 (2)	C15—H15	0.9300
C7—H7	0.9300	C16—H16	0.9300
C8—O3	1.1961 (19)	C17—O4	1.419 (2)
C8—O2	1.3646 (18)	C17—H17A	0.9600
C8—C9	1.457 (2)	C17—H17B	0.9600
C9—C10	1.321 (2)	C17—H17C	0.9600
C2—C1—C6	121.71 (15)	C9—C10—H10	116.0
C2—C1—O2	118.45 (15)	C11—C10—H10	116.0
C6—C1—O2	119.70 (15)	C16—C11—C12	117.72 (15)
O4—C2—C1	116.23 (15)	C16—C11—C10	119.85 (16)
O4—C2—C3	125.74 (18)	C12—C11—C10	122.41 (15)
C1—C2—C3	118.03 (17)	C13—C12—C11	120.51 (17)
C2—C3—C4	120.37 (19)	C13—C12—H12	119.7
C2—C3—H3	119.8	C11—C12—H12	119.7
C4—C3—H3	119.8	C14—C13—C12	120.87 (19)
C5—C4—C3	120.80 (18)	C14—C13—H13	119.6
C5—C4—H4	119.6	C12—C13—H13	119.6
C3—C4—H4	119.6	C15—C14—C13	119.51 (18)
C4—C5—C6	119.83 (18)	C15—C14—H14	120.2
C4—C5—H5	120.1	C13—C14—H14	120.2
C6—C5—H5	120.1	C14—C15—C16	120.12 (18)
C1—C6—C5	119.24 (18)	C14—C15—H15	119.9
C1—C6—C7	120.93 (16)	C16—C15—H15	119.9
C5—C6—C7	119.82 (17)	C15—C16—C11	121.26 (18)
O1—C7—C6	124.4 (2)	C15—C16—H16	119.4
O1—C7—H7	117.8	C11—C16—H16	119.4
C6—C7—H7	117.8	O4—C17—H17A	109.5
O3—C8—O2	122.24 (14)	O4—C17—H17B	109.5
O3—C8—C9	127.58 (15)	H17A—C17—H17B	109.5
O2—C8—C9	110.17 (14)	O4—C17—H17C	109.5
C10—C9—C8	121.24 (16)	H17A—C17—H17C	109.5
C10—C9—H9	119.4	H17B—C17—H17C	109.5
C8—C9—H9	119.4	C8—O2—C1	117.06 (12)
C9—C10—C11	128.01 (16)	C2—O4—C17	117.68 (16)
C6—C1—C2—O4	179.15 (15)	C8—C9—C10—C11	−175.41 (15)
O2—C1—C2—O4	−5.3 (2)	C9—C10—C11—C16	178.04 (17)
C6—C1—C2—C3	−1.7 (2)	C9—C10—C11—C12	−0.6 (3)
O2—C1—C2—C3	173.89 (14)	C16—C11—C12—C13	−0.9 (3)
O4—C2—C3—C4	179.98 (17)	C10—C11—C12—C13	177.80 (17)
C1—C2—C3—C4	0.9 (3)	C11—C12—C13—C14	0.1 (3)
C2—C3—C4—C5	0.3 (3)	C12—C13—C14—C15	0.8 (3)
C3—C4—C5—C6	−0.8 (3)	C13—C14—C15—C16	−0.7 (3)
C2—C1—C6—C5	1.2 (2)	C14—C15—C16—C11	−0.1 (3)
O2—C1—C6—C5	−174.30 (14)	C12—C11—C16—C15	0.9 (3)
C2—C1—C6—C7	−179.88 (16)	C10—C11—C16—C15	−177.80 (17)
O2—C1—C6—C7	4.6 (2)	O3—C8—O2—C1	10.1 (2)
C4—C5—C6—C1	0.0 (3)	C9—C8—O2—C1	−169.00 (14)
C4—C5—C6—C7	−178.85 (17)	C2—C1—O2—C8	78.41 (18)
C1—C6—C7—O1	173.14 (19)	C6—C1—O2—C8	−105.90 (17)
C5—C6—C7—O1	−8.0 (3)	C1—C2—O4—C17	174.31 (16)
O3—C8—C9—C10	−10.2 (3)	C3—C2—O4—C17	−4.8 (3)
O2—C8—C9—C10	168.89 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O3i	0.93	2.50	3.415 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O3i	0.93	2.50	3.415 (2)	168

Symmetry code: (i) .