Octyl 3-(3,4-dihydroxy­phen­yl)prop-2-enoate

Xia, C.-N.; Hu, W.-X.; Zhou, W.

doi:10.1107/S1600536806031588

Octyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

The title molecule, C₁₇H₂₄O₄, has an E configuration and shows normal values of bond lengths and angles. A bow angle was revealed in the longer ester group. The hydroxy groups contribute to intermolecular O—H

O hydrogen bonds, which link the molecules into ribbons extended in the ( $\overline{1}$ 10) direction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031588/cv2097sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031588/cv2097Isup2.hkl Contains datablock I

CCDC reference: 614948

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Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C)= 0.004 Å
R factor = 0.062
wR factor = 0.181
Data-to-parameter ratio = 16.3

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No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2003); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Octyl 3-(3,4-dihydroxyphenyl)prop-2-enoate top

Crystal data top

C₁₇H₂₄O₄	Z = 2
M_r = 292.36	F(000) = 316
Triclinic, P1	D_x = 1.194 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.454 (2) Å	Cell parameters from 1016 reflections
b = 12.152 (5) Å	θ = 3.3–23.8°
c = 12.584 (5) Å	µ = 0.08 mm⁻¹
α = 87.763 (6)°	T = 298 K
β = 80.560 (6)°	Prism, light brown
γ = 81.395 (5)°	0.25 × 0.20 × 0.20 mm
V = 813.4 (6) Å³

Data collection top

Bruker APEX CCD area-detector diffractometer	3137 independent reflections
Radiation source: fine-focus sealed tube	1607 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 26.0°, θ_min = 1.6°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −6→5
T_min = 0.969, T_max = 0.983	k = −14→14
3778 measured reflections	l = −15→15

Refinement top

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.181	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0897P)²] where P = (F_o² + 2F_c²)/3
3137 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.1190 (3)	0.86346 (13)	0.00558 (15)	0.0648 (6)
H1	0.2410	0.8268	−0.0301	0.097*
O2	−0.3489 (3)	0.95106 (13)	0.10023 (16)	0.0713 (6)
H2	−0.2393	0.9803	0.0618	0.107*
O3	0.4843 (3)	0.27442 (14)	0.10354 (16)	0.0794 (6)
O4	0.1036 (3)	0.27056 (13)	0.19768 (14)	0.0609 (5)
C1	−0.0994 (4)	0.61545 (19)	0.14443 (19)	0.0502 (6)
C2	0.0540 (4)	0.68337 (19)	0.08245 (19)	0.0513 (6)
H2A	0.2149	0.6526	0.0511	0.062*
C3	−0.0240 (4)	0.79357 (19)	0.06626 (18)	0.0487 (6)
C4	−0.2652 (4)	0.84122 (19)	0.1139 (2)	0.0523 (6)
C5	−0.4185 (5)	0.7756 (2)	0.1752 (2)	0.0610 (7)
H5	−0.5790	0.8067	0.2067	0.073*
C6	−0.3390 (4)	0.6645 (2)	0.1908 (2)	0.0589 (7)
H6	−0.4461	0.6213	0.2328	0.071*
C7	−0.0194 (5)	0.49747 (19)	0.16097 (19)	0.0542 (7)
H7	−0.1356	0.4581	0.2024	0.065*
C8	0.2019 (5)	0.4400 (2)	0.1232 (2)	0.0596 (7)
H8	0.3197	0.4791	0.0825	0.072*
C9	0.2771 (5)	0.3221 (2)	0.1394 (2)	0.0557 (7)
C10	0.1725 (5)	0.15266 (19)	0.2168 (2)	0.0586 (7)
H10A	0.3198	0.1400	0.2521	0.070*
H10B	0.2116	0.1136	0.1490	0.070*
C11	−0.0438 (4)	0.11071 (19)	0.2868 (2)	0.0588 (7)
H11A	−0.1896	0.1227	0.2505	0.071*
H11B	−0.0851	0.1518	0.3534	0.071*
C12	0.0197 (4)	−0.0119 (2)	0.3118 (2)	0.0584 (7)
H12A	0.1703	−0.0231	0.3449	0.070*
H12B	0.0575	−0.0521	0.2446	0.070*
C13	−0.1854 (5)	−0.0614 (2)	0.3854 (2)	0.0627 (7)
H13A	−0.2291	−0.0193	0.4514	0.075*
H13B	−0.3336	−0.0539	0.3509	0.075*
C14	−0.1134 (5)	−0.1825 (2)	0.4135 (2)	0.0644 (7)
H14A	0.0356	−0.1901	0.4475	0.077*
H14B	−0.0710	−0.2247	0.3475	0.077*
C15	−0.3177 (5)	−0.2321 (2)	0.4878 (2)	0.0727 (8)
H15A	−0.3685	−0.1865	0.5515	0.087*
H15B	−0.4625	−0.2290	0.4516	0.087*
C16	−0.2426 (6)	−0.3503 (3)	0.5226 (3)	0.0953 (11)
H16A	−0.0951	−0.3538	0.5572	0.114*
H16B	−0.1963	−0.3963	0.4591	0.114*
C17	−0.4453 (7)	−0.3981 (3)	0.5991 (3)	0.1152 (13)
H17A	−0.4915	−0.3536	0.6626	0.173*
H17B	−0.3834	−0.4730	0.6188	0.173*
H17C	−0.5896	−0.3981	0.5645	0.173*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0547 (11)	0.0407 (10)	0.0872 (13)	0.0007 (8)	0.0141 (9)	0.0080 (9)
O2	0.0583 (11)	0.0448 (11)	0.0979 (15)	0.0086 (8)	0.0087 (10)	0.0073 (10)
O3	0.0584 (12)	0.0575 (12)	0.1027 (14)	0.0077 (9)	0.0274 (11)	0.0068 (10)
O4	0.0494 (10)	0.0421 (10)	0.0811 (12)	0.0012 (8)	0.0106 (9)	0.0041 (9)
C1	0.0451 (14)	0.0429 (15)	0.0595 (15)	−0.0050 (11)	−0.0003 (12)	0.0003 (12)
C2	0.0401 (13)	0.0415 (15)	0.0661 (16)	0.0024 (10)	0.0025 (12)	−0.0016 (12)
C3	0.0420 (13)	0.0419 (15)	0.0586 (15)	−0.0055 (11)	0.0019 (12)	0.0006 (12)
C4	0.0452 (14)	0.0404 (15)	0.0667 (16)	0.0012 (11)	−0.0021 (13)	−0.0022 (12)
C5	0.0428 (14)	0.0531 (17)	0.0788 (18)	0.0020 (12)	0.0067 (13)	−0.0018 (14)
C6	0.0460 (15)	0.0503 (16)	0.0736 (17)	−0.0072 (12)	0.0093 (13)	0.0020 (13)
C7	0.0522 (15)	0.0439 (15)	0.0612 (16)	−0.0065 (11)	0.0060 (13)	0.0008 (12)
C8	0.0556 (16)	0.0463 (16)	0.0691 (17)	−0.0068 (12)	0.0116 (13)	0.0045 (13)
C9	0.0504 (15)	0.0478 (15)	0.0618 (16)	−0.0037 (12)	0.0074 (13)	0.0030 (12)
C10	0.0529 (15)	0.0416 (15)	0.0750 (17)	0.0016 (11)	−0.0004 (14)	0.0050 (13)
C11	0.0471 (15)	0.0538 (17)	0.0699 (17)	−0.0027 (12)	0.0018 (13)	0.0034 (13)
C12	0.0486 (15)	0.0494 (16)	0.0729 (16)	−0.0043 (11)	−0.0007 (13)	0.0050 (13)
C13	0.0535 (15)	0.0580 (18)	0.0728 (17)	−0.0074 (12)	0.0001 (14)	0.0006 (14)
C14	0.0556 (16)	0.0569 (18)	0.0791 (18)	−0.0098 (13)	−0.0069 (14)	0.0101 (14)
C15	0.0709 (18)	0.066 (2)	0.0791 (19)	−0.0164 (14)	−0.0041 (16)	0.0100 (16)
C16	0.099 (3)	0.073 (2)	0.112 (3)	−0.0262 (18)	−0.008 (2)	0.0269 (19)
C17	0.134 (3)	0.099 (3)	0.114 (3)	−0.051 (2)	−0.002 (3)	0.031 (2)

Geometric parameters (Å, º) top

O1—C3	1.365 (3)	C10—H10B	0.9700
O1—H1	0.8200	C11—C12	1.511 (3)
O2—C4	1.358 (3)	C11—H11A	0.9700
O2—H2	0.8200	C11—H11B	0.9700
O3—C9	1.213 (3)	C12—C13	1.514 (3)
O4—C9	1.319 (3)	C12—H12A	0.9700
O4—C10	1.447 (3)	C12—H12B	0.9700
C1—C2	1.390 (3)	C13—C14	1.508 (3)
C1—C6	1.395 (3)	C13—H13A	0.9700
C1—C7	1.452 (3)	C13—H13B	0.9700
C2—C3	1.361 (3)	C14—C15	1.515 (3)
C2—H2A	0.9300	C14—H14A	0.9700
C3—C4	1.402 (3)	C14—H14B	0.9700
C4—C5	1.367 (3)	C15—C16	1.502 (4)
C5—C6	1.372 (3)	C15—H15A	0.9700
C5—H5	0.9300	C15—H15B	0.9700
C6—H6	0.9300	C16—C17	1.512 (4)
C7—C8	1.325 (3)	C16—H16A	0.9700
C7—H7	0.9300	C16—H16B	0.9700
C8—C9	1.446 (3)	C17—H17A	0.9599
C8—H8	0.9300	C17—H17B	0.9599
C10—C11	1.494 (3)	C17—H17C	0.9599
C10—H10A	0.9700

C3—O1—H1	109.5	C10—C11—H11B	109.5
C4—O2—H2	109.5	C12—C11—H11B	109.5
C9—O4—C10	116.32 (18)	H11A—C11—H11B	108.1
C2—C1—C6	117.5 (2)	C11—C12—C13	114.6 (2)
C2—C1—C7	122.5 (2)	C11—C12—H12A	108.6
C6—C1—C7	120.1 (2)	C13—C12—H12A	108.6
C3—C2—C1	122.0 (2)	C11—C12—H12B	108.6
C3—C2—H2A	119.0	C13—C12—H12B	108.6
C1—C2—H2A	119.0	H12A—C12—H12B	107.6
C2—C3—O1	124.2 (2)	C14—C13—C12	113.7 (2)
C2—C3—C4	119.6 (2)	C14—C13—H13A	108.8
O1—C3—C4	116.3 (2)	C12—C13—H13A	108.8
O2—C4—C5	119.6 (2)	C14—C13—H13B	108.8
O2—C4—C3	121.2 (2)	C12—C13—H13B	108.8
C5—C4—C3	119.2 (2)	H13A—C13—H13B	107.7
C4—C5—C6	120.9 (2)	C13—C14—C15	113.8 (2)
C4—C5—H5	119.5	C13—C14—H14A	108.8
C6—C5—H5	119.5	C15—C14—H14A	108.8
C5—C6—C1	120.8 (2)	C13—C14—H14B	108.8
C5—C6—H6	119.6	C15—C14—H14B	108.8
C1—C6—H6	119.6	H14A—C14—H14B	107.7
C8—C7—C1	126.8 (2)	C16—C15—C14	114.4 (2)
C8—C7—H7	116.6	C16—C15—H15A	108.6
C1—C7—H7	116.6	C14—C15—H15A	108.6
C7—C8—C9	126.0 (2)	C16—C15—H15B	108.6
C7—C8—H8	117.0	C14—C15—H15B	108.6
C9—C8—H8	117.0	H15A—C15—H15B	107.6
O3—C9—O4	122.5 (2)	C15—C16—C17	114.1 (3)
O3—C9—C8	122.9 (2)	C15—C16—H16A	108.7
O4—C9—C8	114.6 (2)	C17—C16—H16A	108.7
O4—C10—C11	108.24 (19)	C15—C16—H16B	108.7
O4—C10—H10A	110.0	C17—C16—H16B	108.7
C11—C10—H10A	110.0	H16A—C16—H16B	107.6
O4—C10—H10B	110.0	C16—C17—H17A	109.5
C11—C10—H10B	110.0	C16—C17—H17B	109.5
H10A—C10—H10B	108.4	H17A—C17—H17B	109.5
C10—C11—C12	110.65 (19)	C16—C17—H17C	109.5
C10—C11—H11A	109.5	H17A—C17—H17C	109.5
C12—C11—H11A	109.5	H17B—C17—H17C	109.5

C6—C1—C2—C3	−0.4 (4)	C6—C1—C7—C8	−179.3 (3)
C7—C1—C2—C3	179.1 (2)	C1—C7—C8—C9	−179.1 (2)
C1—C2—C3—O1	−179.6 (2)	C10—O4—C9—O3	−0.2 (4)
C1—C2—C3—C4	0.6 (4)	C10—O4—C9—C8	−179.3 (2)
C2—C3—C4—O2	179.5 (2)	C7—C8—C9—O3	−179.1 (3)
O1—C3—C4—O2	−0.3 (4)	C7—C8—C9—O4	−0.1 (4)
C2—C3—C4—C5	−0.6 (4)	C9—O4—C10—C11	178.1 (2)
O1—C3—C4—C5	179.6 (2)	O4—C10—C11—C12	−178.7 (2)
O2—C4—C5—C6	−179.8 (2)	C10—C11—C12—C13	178.1 (2)
C3—C4—C5—C6	0.3 (4)	C11—C12—C13—C14	−177.2 (2)
C4—C5—C6—C1	−0.1 (4)	C12—C13—C14—C15	179.6 (2)
C2—C1—C6—C5	0.1 (4)	C13—C14—C15—C16	−176.0 (3)
C7—C1—C6—C5	−179.4 (2)	C14—C15—C16—C17	178.5 (3)
C2—C1—C7—C8	1.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	2.26	2.711 (2)	115
O2—H2···O1ⁱ	0.82	2.20	2.914 (2)	146
O1—H1···O3ⁱⁱ	0.82	1.92	2.738 (2)	173
C2—H2A···O3ⁱⁱ	0.93	2.55	3.231 (3)	130

Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y+1, −z.

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Octyl 3-(3,4-dihydroxy­phen­yl)prop-2-enoate

Supporting information

Key indicators

checkCIF/PLATON results

Octyl 3-(3,4-dihydroxyphenyl)prop-2-enoate