(10E,12E,14E)-9,16-Dioxoocta-deca-10,12,14-trienoic acid.

The title octa-deca-trienoic acid derivative, C(18)H(26)O(4), was isolated from Silene maritima With. (Caryophyllaceae), the first time this natural compound has been found in the Caryophyllales order. This fatty acid has an 18-carbon backbone with three double bonds on trans (E) conformation and two carbonyl. In the crystal, molecules are linked via pairs of O-H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For botanical information about Silene maritima With., see: Baker (1978 ▶); Bremer et al. (2009 ▶). For interactions between heavy-metals and Silene maritima With., see: Price & Abrahams (1994 ▶). For phytochemical investigation on Silene maritima With., see: Adrian-Romero et al. (1998 ▶). For previous descriptions of the title compound, see: Herz & Kulanthaivel (1984 ▶); Li et al. (2011 ▶). For lipoxygenase action on α-linoleic acid, see: Vellosillo et al. (2007 ▶). For environmental-stress-response involvement of oxylipines and their structure similarity with the title compound, see: Browse (2005 ▶); Schaller et al. (2004 ▶); Wasternack (2007 ▶).

Experimental

Crystal data

C18H26O4

M = 306.39

Triclinic,

a = 5.6859 (3) Å

b = 7.7535 (5) Å

c = 19.9045 (16) Å

α = 81.333 (4)°

β = 84.152 (4)°

γ = 87.660 (4)°

V = 862.68 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.40 × 0.30 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

8217 measured reflections

3846 independent reflections

2648 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.189

S = 1.06

3846 reflections

204 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.24 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: DENZO; 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812027870/zj2081sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027870/zj2081Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027870/zj2081Isup3.cml

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

C18H26O4	Z = 2
Mr = 306.39	F(000) = 332
Triclinic, P1	Dx = 1.180 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6859 (3) Å	Cell parameters from 12739 reflections
b = 7.7535 (5) Å	θ = 1.0–27.5°
c = 19.9045 (16) Å	µ = 0.08 mm−1
α = 81.333 (4)°	T = 173 K
β = 84.152 (4)°	Plate, colorless
γ = 87.660 (4)°	0.40 × 0.30 × 0.10 mm
V = 862.68 (10) Å3

Nonius KappaCCD diffractometer	2648 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.063
Graphite monochromator	θmax = 27.5°, θmin = 1.0°
phi and ω scans	h = −7→7
8217 measured reflections	k = −10→10
3846 independent reflections	l = −25→25

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0932P)2 + 0.1679P] where P = (Fo2 + 2Fc2)/3
3846 reflections	(Δ/σ)max < 0.001
204 parameters	Δρmax = 0.27 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	1.7412 (3)	0.9602 (2)	0.07113 (9)	0.0370 (4)
C2	1.5281 (3)	0.9351 (3)	0.12198 (10)	0.0426 (5)
H2A	1.3914	0.9132	0.0977	0.051*
H2B	1.4935	1.0453	0.1410	0.051*
C3	1.5485 (3)	0.7882 (2)	0.18074 (9)	0.0355 (4)
H3A	1.6700	0.8163	0.2094	0.043*
H3B	1.5999	0.6793	0.1625	0.043*
C4	1.3134 (3)	0.7601 (2)	0.22433 (9)	0.0371 (4)
H4A	1.2613	0.8705	0.2413	0.044*
H4B	1.1935	0.7311	0.1954	0.044*
C5	1.3238 (3)	0.6162 (2)	0.28491 (9)	0.0349 (4)
H5A	1.4352	0.6489	0.3157	0.042*
H5B	1.3859	0.5074	0.2684	0.042*
C6	1.0834 (3)	0.5817 (2)	0.32511 (9)	0.0344 (4)
H6A	1.0212	0.6904	0.3417	0.041*
H6B	0.9720	0.5489	0.2944	0.041*
C7	1.0945 (3)	0.4374 (2)	0.38581 (9)	0.0332 (4)
H7A	1.2019	0.4722	0.4173	0.040*
H7B	1.1622	0.3300	0.3693	0.040*
C8	0.8539 (3)	0.3977 (2)	0.42492 (8)	0.0310 (4)
H8A	0.7810	0.5074	0.4381	0.037*
H8B	0.7506	0.3545	0.3942	0.037*
C9	0.8631 (3)	0.2648 (2)	0.48833 (9)	0.0295 (4)
C10	0.6343 (3)	0.2012 (2)	0.52376 (8)	0.0300 (4)
H10	0.4917	0.2397	0.5045	0.036*
C11	0.6245 (3)	0.0905 (2)	0.58252 (9)	0.0299 (4)
H11	0.7696	0.0515	0.6002	0.036*
C12	0.4081 (3)	0.0265 (2)	0.62080 (9)	0.0298 (4)
H12	0.2623	0.0608	0.6027	0.036*
C13	0.4038 (3)	−0.0797 (2)	0.68114 (9)	0.0303 (4)
H13	0.5503	−0.1168	0.6984	0.036*
C14	0.1889 (3)	−0.1398 (2)	0.72083 (8)	0.0291 (4)
H14	0.0433	−0.1026	0.7031	0.035*
C15	0.1797 (3)	−0.2443 (2)	0.78105 (9)	0.0318 (4)
H15	0.3235	−0.2847	0.7992	0.038*
C16	−0.0463 (3)	−0.2989 (2)	0.82020 (9)	0.0295 (4)
C17	−0.0310 (3)	−0.4111 (3)	0.88816 (10)	0.0420 (5)
H17A	0.0712	−0.3535	0.9150	0.050*
H17B	0.0468	−0.5239	0.8804	0.050*
C18	−0.2653 (4)	−0.4474 (3)	0.93005 (10)	0.0502 (5)
H18A	−0.3392	−0.3374	0.9411	0.075*
H18B	−0.2393	−0.5251	0.9724	0.075*
H18C	−0.3693	−0.5032	0.9039	0.075*
O1	1.9060 (2)	0.85667 (18)	0.06800 (7)	0.0537 (4)
O2	1.7321 (3)	1.10716 (19)	0.02820 (8)	0.0565 (4)
O3	1.0497 (2)	0.21570 (18)	0.51052 (7)	0.0464 (4)
O4	−0.2355 (2)	−0.25612 (17)	0.79837 (6)	0.0434 (4)
H2	1.868 (7)	1.118 (5)	0.001 (2)	0.140 (14)*

	U11	U22	U33	U12	U13	U23
C1	0.0422 (10)	0.0350 (9)	0.0294 (9)	−0.0042 (8)	0.0027 (8)	0.0061 (7)
C2	0.0401 (10)	0.0458 (11)	0.0351 (10)	−0.0011 (8)	0.0066 (8)	0.0093 (8)
C3	0.0367 (9)	0.0362 (9)	0.0293 (9)	−0.0033 (7)	0.0052 (7)	0.0037 (7)
C4	0.0362 (10)	0.0399 (10)	0.0306 (9)	−0.0047 (8)	0.0049 (7)	0.0050 (8)
C5	0.0352 (9)	0.0362 (9)	0.0299 (9)	−0.0051 (7)	0.0042 (7)	0.0021 (7)
C6	0.0346 (9)	0.0356 (9)	0.0293 (9)	−0.0053 (7)	0.0039 (7)	0.0041 (7)
C7	0.0310 (9)	0.0343 (9)	0.0308 (9)	−0.0053 (7)	0.0030 (7)	0.0031 (7)
C8	0.0296 (9)	0.0340 (9)	0.0267 (9)	−0.0050 (7)	−0.0010 (7)	0.0041 (7)
C9	0.0275 (8)	0.0321 (9)	0.0274 (8)	−0.0046 (7)	−0.0020 (7)	0.0009 (7)
C10	0.0265 (8)	0.0342 (9)	0.0277 (9)	−0.0034 (7)	−0.0034 (7)	0.0023 (7)
C11	0.0253 (8)	0.0324 (9)	0.0303 (9)	−0.0029 (7)	−0.0032 (7)	0.0015 (7)
C12	0.0275 (8)	0.0322 (9)	0.0278 (9)	−0.0026 (7)	−0.0025 (7)	0.0027 (7)
C13	0.0259 (8)	0.0328 (9)	0.0299 (9)	−0.0028 (7)	−0.0028 (7)	0.0030 (7)
C14	0.0260 (8)	0.0311 (8)	0.0285 (9)	−0.0011 (7)	−0.0032 (7)	0.0017 (7)
C15	0.0253 (8)	0.0345 (9)	0.0324 (9)	−0.0019 (7)	−0.0035 (7)	0.0059 (7)
C16	0.0276 (8)	0.0291 (8)	0.0293 (9)	−0.0010 (7)	−0.0030 (7)	0.0034 (7)
C17	0.0349 (9)	0.0471 (11)	0.0369 (10)	−0.0026 (8)	−0.0018 (8)	0.0157 (8)
C18	0.0468 (12)	0.0550 (12)	0.0389 (11)	−0.0009 (9)	0.0072 (9)	0.0176 (9)
O1	0.0502 (8)	0.0507 (8)	0.0466 (9)	0.0085 (7)	0.0175 (6)	0.0193 (7)
O2	0.0603 (10)	0.0444 (8)	0.0501 (9)	0.0071 (7)	0.0212 (7)	0.0200 (7)
O3	0.0292 (7)	0.0591 (9)	0.0442 (8)	−0.0057 (6)	−0.0048 (6)	0.0166 (6)
O4	0.0275 (6)	0.0587 (9)	0.0382 (7)	−0.0020 (6)	−0.0040 (5)	0.0127 (6)

C1—O1	1.211 (2)	C9—O3	1.215 (2)
C1—O2	1.320 (2)	C9—C10	1.481 (2)
C1—C2	1.497 (3)	C10—C11	1.340 (2)
C2—C3	1.515 (2)	C10—H10	0.9500
C2—H2A	0.9900	C11—C12	1.444 (2)
C2—H2B	0.9900	C11—H11	0.9500
C3—C4	1.522 (2)	C12—C13	1.349 (2)
C3—H3A	0.9900	C12—H12	0.9500
C3—H3B	0.9900	C13—C14	1.440 (2)
C4—C5	1.519 (2)	C13—H13	0.9500
C4—H4A	0.9900	C14—C15	1.339 (2)
C4—H4B	0.9900	C14—H14	0.9500
C5—C6	1.524 (2)	C15—C16	1.476 (2)
C5—H5A	0.9900	C15—H15	0.9500
C5—H5B	0.9900	C16—O4	1.2161 (19)
C6—C7	1.522 (2)	C16—C17	1.502 (2)
C6—H6A	0.9900	C17—C18	1.511 (3)
C6—H6B	0.9900	C17—H17A	0.9900
C7—C8	1.523 (2)	C17—H17B	0.9900
C7—H7A	0.9900	C18—H18A	0.9800
C7—H7B	0.9900	C18—H18B	0.9800
C8—C9	1.508 (2)	C18—H18C	0.9800
C8—H8A	0.9900	O2—H2	0.90 (4)
C8—H8B	0.9900
O1—C1—O2	122.25 (17)	C7—C8—H8A	108.8
O1—C1—C2	124.48 (16)	C9—C8—H8B	108.8
O2—C1—C2	113.26 (16)	C7—C8—H8B	108.8
C1—C2—C3	115.59 (15)	H8A—C8—H8B	107.7
C1—C2—H2A	108.4	O3—C9—C10	121.41 (15)
C3—C2—H2A	108.4	O3—C9—C8	121.50 (15)
C1—C2—H2B	108.4	C10—C9—C8	117.06 (14)
C3—C2—H2B	108.4	C11—C10—C9	121.25 (15)
H2A—C2—H2B	107.4	C11—C10—H10	119.4
C2—C3—C4	111.17 (15)	C9—C10—H10	119.4
C2—C3—H3A	109.4	C10—C11—C12	124.38 (15)
C4—C3—H3A	109.4	C10—C11—H11	117.8
C2—C3—H3B	109.4	C12—C11—H11	117.8
C4—C3—H3B	109.4	C13—C12—C11	122.93 (15)
H3A—C3—H3B	108.0	C13—C12—H12	118.5
C5—C4—C3	113.63 (15)	C11—C12—H12	118.5
C5—C4—H4A	108.8	C12—C13—C14	123.43 (15)
C3—C4—H4A	108.8	C12—C13—H13	118.3
C5—C4—H4B	108.8	C14—C13—H13	118.3
C3—C4—H4B	108.8	C15—C14—C13	124.62 (15)
H4A—C4—H4B	107.7	C15—C14—H14	117.7
C4—C5—C6	112.83 (15)	C13—C14—H14	117.7
C4—C5—H5A	109.0	C14—C15—C16	122.26 (15)
C6—C5—H5A	109.0	C14—C15—H15	118.9
C4—C5—H5B	109.0	C16—C15—H15	118.9
C6—C5—H5B	109.0	O4—C16—C15	121.69 (15)
H5A—C5—H5B	107.8	O4—C16—C17	121.60 (15)
C7—C6—C5	112.67 (15)	C15—C16—C17	116.71 (14)
C7—C6—H6A	109.1	C16—C17—C18	115.05 (15)
C5—C6—H6A	109.1	C16—C17—H17A	108.5
C7—C6—H6B	109.1	C18—C17—H17A	108.5
C5—C6—H6B	109.1	C16—C17—H17B	108.5
H6A—C6—H6B	107.8	C18—C17—H17B	108.5
C6—C7—C8	113.09 (14)	H17A—C17—H17B	107.5
C6—C7—H7A	109.0	C17—C18—H18A	109.5
C8—C7—H7A	109.0	C17—C18—H18B	109.5
C6—C7—H7B	109.0	H18A—C18—H18B	109.5
C8—C7—H7B	109.0	C17—C18—H18C	109.5
H7A—C7—H7B	107.8	H18A—C18—H18C	109.5
C9—C8—C7	113.98 (14)	H18B—C18—H18C	109.5
C9—C8—H8A	108.8	C1—O2—H2	109 (2)
O1—C1—C2—C3	12.6 (3)	C8—C9—C10—C11	−176.26 (15)
O2—C1—C2—C3	−168.51 (16)	C9—C10—C11—C12	178.37 (15)
C1—C2—C3—C4	−173.08 (16)	C10—C11—C12—C13	−177.39 (16)
C2—C3—C4—C5	−179.00 (15)	C11—C12—C13—C14	177.91 (15)
C3—C4—C5—C6	−176.13 (15)	C12—C13—C14—C15	−179.56 (16)
C4—C5—C6—C7	−179.98 (14)	C13—C14—C15—C16	178.72 (15)
C5—C6—C7—C8	−178.05 (14)	C14—C15—C16—O4	2.6 (3)
C6—C7—C8—C9	−175.62 (14)	C14—C15—C16—C17	−177.86 (16)
C7—C8—C9—O3	10.3 (3)	O4—C16—C17—C18	−7.0 (3)
C7—C8—C9—C10	−171.76 (14)	C15—C16—C17—C18	173.45 (16)
O3—C9—C10—C11	1.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.90 (4)	1.78 (4)	2.658 (2)	167.0 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.90 (4)	1.78 (4)	2.658 (2)	167.0 (4)

Symmetry code: (i) .