3-Eth­oxy-4-hydroxy­benzaldehyde

Li, Y.; Zhang, X.; Zheng, J.; Wang, X.

doi:10.1107/S1600536808030419

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o2008

doi:10.1107/S1600536808030419

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3-Ethoxy-4-hydroxybenzaldehyde

Yong Li,^a ^* Xinxi Zhang,^a Jun Zheng ^a and Xiaoling Wang ^b

^aDepartment of Environmental Engineering, Anhui University of Technology, Maanshan 243002, People's Republic of China, and ^bAnalysis and Testing Central Facility, Anhui University of Technology, Maanshan 243002, People's Republic of China
^*Correspondence e-mail: farnesene@gmail.com

(Received 20 September 2008; accepted 22 September 2008; online 24 September 2008)

The title compound (ethyl vanillin), C₉H₁₀O₃, an important food additive and flavouring agent approved by FAO/WHO, has a vanilla odor four times that of vanillin and shows antimutagenic activity. There are two molecules in the asymmetric unit, each having a planar conformation and an intramolecular O—H⋯O bond. Molecules are connected side-by-side, building infinite ribbons along c via intermolecular O—H⋯O hydrogen bonds between the carbonyl and hydroxyl groups. The ribbons are then packed into layers perpendicular to the a axis.

Related literature

For anti-mutagenic activity, see: Ohta et al. (1986 ). For the synthetic method, see: Gradeff & Murayama (1982 ). For related literature, see: Li (2008 ).

Experimental

Crystal data

C₉H₁₀O₃
M_r = 166.17
Monoclinic, P 2₁ /c
a = 13.7352 (6) Å
b = 14.4140 (6) Å
c = 8.7890 (4) Å
β = 100.742 (3)°
V = 1709.55 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.50 × 0.50 × 0.40 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
16625 measured reflections
3934 independent reflections
2581 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.155
S = 1.01
3934 reflections
297 parameters
All H-atom parameters refined
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1⋯O1ⁱ	0.79 (3)	2.03 (3)	2.6951 (17)	142 (3)
O2—H1⋯O3	0.79 (3)	2.26 (3)	2.6619 (16)	112 (2)
O12—H14⋯O11ⁱⁱ	0.81 (3)	2.02 (3)	2.7117 (19)	143 (3)
O12—H14⋯O13	0.81 (3)	2.26 (3)	2.6554 (18)	111 (2)
Symmetry codes: (i) x, y, z+1; (ii) x, y, z-1.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT-Plus (Bruker, 2003 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030419/dn2380sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030419/dn2380Isup2.hkl

checkCIF report

Comment top

The title compound, an ethyl analogue of vanillin, is an important food additive and flavouring agent approved by FAO/WHO. Its vanilla odor is four times stronger than the flavour of vanillin. Now, it is widely used in food, beverage, cigarette and cosmetics. This synthetic compound was reported to show marked anti-mutagenic activity against mutagenicity induced by 4-nitroquinoline-1-oxide, furylfuramide, captan or methylglyoxal, similar to another report (Li, 2008). It was assumed that the anti-mutagenic activity was due to enhancement of an error-free recombinational repair system (Ohta et al., 1986). But the structure of ethyl vanillin has never been reported. we then report herein its crystal structure determination (Fig.1). The crystal structure consists of layers of planar molecules linked as one-dimensional chains (Fig. 2).

Related literature top

For anti-mutagenic activity, see: Ohta et al. (1986). For the synthetic method, see: Gradeff & Murayama (1982). For related literature, see: Li (2008).

Experimental top

One of the synthetic methods was reported by literature(Gradeff & Murayama, 1982). The crude title compound commercially available was recrystallized two times from EtOH/water (1:1) solution, and then colourless block crystals were collected after slow evaporation at room temperature.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Partial packing view of the title compound, showing one layer of molecules connected by O—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bondings have been removed for clarity.

3-Ethoxy-4-hydroxybenzaldehyde top

Crystal data top

C₉H₁₀O₃	F(000) = 704
M_r = 166.17	D_x = 1.291 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 17141 reflections
a = 13.7352 (6) Å	θ = 2.1–27.6°
b = 14.4140 (6) Å	µ = 0.10 mm⁻¹
c = 8.7890 (4) Å	T = 296 K
β = 100.742 (3)°	Block, colourless
V = 1709.55 (13) Å³	0.50 × 0.50 × 0.40 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	2581 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 27.6°, θ_min = 2.1°
Thin–slice ω scans	h = −17→17
16625 measured reflections	k = −18→18
3934 independent reflections	l = −11→11

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	All H-atom parameters refined
S = 1.02	w = 1/[σ²(F_o²) + (0.0737P)² + 0.3872P] where P = (F_o² + 2F_c²)/3
3934 reflections	(Δ/σ)_max < 0.001
297 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₉H₁₀O₃	V = 1709.55 (13) Å³
M_r = 166.17	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.7352 (6) Å	µ = 0.10 mm⁻¹
b = 14.4140 (6) Å	T = 296 K
c = 8.7890 (4) Å	0.50 × 0.50 × 0.40 mm
β = 100.742 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2581 reflections with I > 2σ(I)
16625 measured reflections	R_int = 0.025
3934 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.155	All H-atom parameters refined
S = 1.02	Δρ_max = 0.20 e Å⁻³
3934 reflections	Δρ_min = −0.20 e Å⁻³
297 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.12477 (10)	0.43352 (12)	0.28767 (13)	0.0715 (5)
O2	0.12710 (11)	0.36758 (9)	1.00143 (14)	0.0604 (5)
O3	0.12391 (10)	0.54909 (7)	0.94489 (12)	0.0548 (4)
C1	0.12429 (11)	0.45393 (11)	0.55447 (17)	0.0437 (5)
C2	0.12350 (12)	0.51971 (11)	0.67073 (17)	0.0448 (5)
C3	0.12434 (11)	0.49228 (10)	0.82084 (16)	0.0410 (4)
C4	0.12606 (12)	0.39763 (11)	0.85609 (16)	0.0436 (5)
C5	0.12674 (14)	0.33230 (12)	0.74025 (19)	0.0542 (6)
C6	0.12612 (13)	0.36096 (12)	0.59045 (18)	0.0501 (5)
C7	0.12395 (14)	0.48538 (14)	0.39633 (19)	0.0558 (6)
C8	0.12357 (18)	0.64675 (12)	0.9186 (2)	0.0601 (7)
C9	0.1244 (2)	0.69335 (18)	1.0715 (3)	0.0746 (9)
O11	0.37024 (11)	0.56574 (12)	0.86077 (14)	0.0784 (6)
O12	0.37991 (12)	0.63363 (10)	0.15095 (15)	0.0686 (5)
O13	0.37825 (10)	0.45237 (8)	0.20437 (13)	0.0568 (4)
C11	0.37039 (12)	0.54556 (11)	0.59351 (17)	0.0460 (5)
C12	0.37298 (12)	0.48002 (12)	0.47729 (18)	0.0467 (5)
C13	0.37476 (11)	0.50805 (10)	0.32797 (17)	0.0424 (5)
C14	0.37515 (12)	0.60323 (11)	0.29454 (18)	0.0462 (5)
C15	0.37110 (14)	0.66787 (12)	0.40983 (19)	0.0549 (6)
C16	0.36854 (13)	0.63909 (12)	0.5583 (2)	0.0524 (6)
C17	0.37151 (14)	0.51450 (16)	0.7520 (2)	0.0621 (7)
C18	0.37312 (17)	0.35399 (12)	0.2254 (2)	0.0591 (7)
C19	0.3821 (2)	0.30995 (18)	0.0736 (3)	0.0810 (10)
H1	0.1261 (16)	0.4088 (19)	1.061 (3)	0.080 (7)*
H2	0.1292 (12)	0.2659 (16)	0.769 (2)	0.070 (6)*
H3	0.1271 (13)	0.3143 (15)	0.513 (2)	0.064 (5)*
H4	0.1224 (12)	0.5864 (15)	0.642 (2)	0.065 (6)*
H5	0.0633 (18)	0.6778 (17)	1.111 (3)	0.097 (8)*
H6	0.1828 (19)	0.6754 (18)	1.144 (3)	0.101 (8)*
H7	0.1219 (17)	0.753 (2)	1.052 (3)	0.109 (9)*
H8	0.0602 (16)	0.6625 (15)	0.843 (3)	0.082 (7)*
H9	0.1861 (16)	0.6620 (15)	0.876 (2)	0.079 (6)*
H10	0.1194 (14)	0.5560 (16)	0.378 (2)	0.074 (6)*
H11	0.3722 (13)	0.7337 (16)	0.381 (2)	0.074 (6)*
H12	0.3666 (13)	0.6803 (15)	0.638 (2)	0.064 (5)*
H13	0.3747 (12)	0.4127 (15)	0.507 (2)	0.063 (5)*
H14	0.3786 (17)	0.592 (2)	0.088 (3)	0.095 (8)*
H15	0.3753 (13)	0.4451 (15)	0.767 (2)	0.071 (6)*
H16	0.4291 (15)	0.3369 (14)	0.313 (2)	0.075 (6)*
H17	0.3088 (15)	0.3405 (14)	0.256 (2)	0.071 (6)*
H18	0.383 (2)	0.243 (3)	0.097 (4)	0.138 (11)*
H19	0.325 (2)	0.329 (2)	−0.001 (3)	0.110 (9)*
H20	0.445 (2)	0.3290 (18)	0.042 (3)	0.105 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0927 (10)	0.0925 (10)	0.0316 (6)	0.0006 (8)	0.0175 (6)	−0.0063 (6)
O2	0.1121 (11)	0.0403 (7)	0.0313 (6)	0.0008 (6)	0.0198 (6)	0.0035 (5)
O3	0.0986 (9)	0.0358 (6)	0.0326 (6)	−0.0012 (6)	0.0188 (5)	−0.0062 (4)
C1	0.0554 (9)	0.0463 (9)	0.0305 (7)	−0.0011 (7)	0.0107 (6)	−0.0016 (6)
C2	0.0664 (10)	0.0357 (8)	0.0333 (8)	−0.0004 (7)	0.0121 (7)	0.0014 (6)
C3	0.0587 (9)	0.0346 (7)	0.0308 (7)	−0.0008 (6)	0.0110 (6)	−0.0041 (6)
C4	0.0660 (10)	0.0364 (8)	0.0297 (7)	0.0002 (7)	0.0125 (6)	0.0016 (6)
C5	0.0917 (13)	0.0337 (8)	0.0389 (8)	0.0001 (8)	0.0169 (8)	−0.0004 (7)
C6	0.0776 (11)	0.0427 (9)	0.0314 (8)	−0.0006 (8)	0.0141 (7)	−0.0081 (7)
C7	0.0722 (11)	0.0635 (12)	0.0327 (8)	−0.0006 (9)	0.0121 (7)	0.0011 (8)
C8	0.0925 (15)	0.0341 (9)	0.0556 (11)	−0.0013 (9)	0.0187 (10)	−0.0071 (8)
C9	0.1020 (19)	0.0521 (12)	0.0708 (15)	0.0004 (12)	0.0193 (13)	−0.0262 (11)
O11	0.1028 (11)	0.0990 (12)	0.0365 (7)	−0.0016 (8)	0.0207 (7)	−0.0071 (7)
O12	0.1270 (12)	0.0454 (7)	0.0374 (7)	0.0021 (7)	0.0254 (7)	0.0043 (6)
O13	0.0963 (9)	0.0380 (6)	0.0384 (6)	0.0026 (6)	0.0188 (6)	−0.0049 (5)
C11	0.0552 (9)	0.0504 (9)	0.0332 (8)	−0.0009 (7)	0.0105 (6)	−0.0028 (7)
C12	0.0628 (10)	0.0391 (9)	0.0393 (8)	−0.0013 (7)	0.0122 (7)	0.0020 (7)
C13	0.0564 (9)	0.0355 (7)	0.0360 (8)	0.0001 (6)	0.0103 (6)	−0.0040 (6)
C14	0.0669 (10)	0.0391 (8)	0.0336 (8)	0.0011 (7)	0.0122 (7)	0.0009 (6)
C15	0.0861 (13)	0.0370 (8)	0.0425 (9)	0.0015 (8)	0.0147 (8)	−0.0047 (7)
C16	0.0704 (11)	0.0473 (9)	0.0408 (9)	0.0010 (8)	0.0134 (8)	−0.0098 (8)
C17	0.0788 (13)	0.0694 (13)	0.0402 (9)	−0.0033 (10)	0.0168 (8)	0.0015 (9)
C18	0.0820 (13)	0.0348 (9)	0.0594 (12)	0.0004 (8)	0.0103 (10)	−0.0076 (8)
C19	0.110 (2)	0.0560 (13)	0.0776 (16)	0.0065 (13)	0.0192 (15)	−0.0263 (12)

Geometric parameters (Å, º) top

O1—C7	1.215 (2)	C8—H8	1.02 (2)
O2—C4	1.3464 (19)	C8—H9	1.02 (2)
O3—C3	1.3644 (17)	C9—H6	0.96 (3)
O3—C8	1.426 (2)	C9—H7	0.88 (3)
O2—H1	0.79 (3)	C9—H5	0.99 (3)
O11—C17	1.211 (2)	C11—C12	1.397 (2)
O12—C14	1.349 (2)	C11—C17	1.461 (2)
O13—C13	1.3587 (19)	C11—C16	1.382 (2)
O13—C18	1.434 (2)	C12—C13	1.378 (2)
O12—H14	0.81 (3)	C13—C14	1.403 (2)
C1—C7	1.461 (2)	C14—C15	1.385 (2)
C1—C6	1.376 (2)	C15—C16	1.376 (2)
C1—C2	1.396 (2)	C18—C19	1.503 (3)
C2—C3	1.375 (2)	C12—H13	1.00 (2)
C3—C4	1.398 (2)	C15—H11	0.98 (2)
C4—C5	1.388 (2)	C16—H12	0.923 (19)
C5—C6	1.378 (2)	C17—H15	1.01 (2)
C8—C9	1.501 (3)	C18—H16	1.012 (19)
C2—H4	0.99 (2)	C18—H17	0.99 (2)
C5—H2	0.99 (2)	C19—H18	0.99 (4)
C6—H3	0.96 (2)	C19—H19	0.96 (3)
C7—H10	1.03 (2)	C19—H20	0.99 (3)

O1···O2ⁱ	2.6951 (17)	C12···H16	2.71 (2)
O2···C6ⁱⁱ	3.386 (2)	C12···H17	2.822 (19)
O2···O3	2.6619 (16)	C14···H6ⁱ	2.92 (3)
O2···O1ⁱⁱⁱ	2.6951 (17)	C16···H16^ix	2.82 (2)
O3···O2	2.6619 (16)	C18···H13	2.612 (18)
O11···O12ⁱⁱⁱ	2.7117 (19)	H1···O1ⁱⁱⁱ	2.03 (3)
O12···O11ⁱ	2.7117 (19)	H1···O3	2.26 (3)
O12···C16^iv	3.372 (2)	H2···H3ⁱⁱ	2.44 (3)
O12···O13	2.6554 (18)	H2···O1ⁱⁱ	2.88 (2)
O13···O12	2.6554 (18)	H3···O2^v	2.62 (2)
O1···H3	2.618 (19)	H3···H2^v	2.44 (3)
O1···H1ⁱ	2.03 (3)	H3···O1	2.618 (19)
O1···H2^v	2.88 (2)	H4···H7^iv	2.45 (4)
O2···H19ⁱⁱⁱ	2.78 (3)	H4···H8	2.37 (3)
O2···H5^vi	2.70 (3)	H4···H9	2.35 (3)
O2···H3ⁱⁱ	2.62 (2)	H4···C8	2.579 (18)
O3···H1	2.26 (3)	H4···H10	2.35 (2)
O11···H9	2.91 (2)	H5···O2^vi	2.70 (3)
O11···H14ⁱⁱⁱ	2.02 (3)	H5···C4^vi	2.88 (3)
O11···H11^vii	2.90 (2)	H6···O12ⁱⁱⁱ	2.76 (3)
O11···H12	2.555 (19)	H6···C14ⁱⁱⁱ	2.92 (3)
O12···H12^iv	2.69 (2)	H7···H4^vii	2.45 (4)
O12···H6ⁱ	2.76 (3)	H8···H4	2.37 (3)
O13···H14	2.26 (3)	H8···C2	2.79 (2)
C1···C11	3.586 (2)	H9···H4	2.35 (3)
C2···C11	3.600 (2)	H9···O11	2.91 (2)
C2···C17	3.349 (3)	H9···C2	2.76 (2)
C2···C7^viii	3.340 (3)	H10···H4	2.35 (2)
C3···C17	3.572 (2)	H11···O11^iv	2.90 (2)
C3···C7^viii	3.599 (2)	H11···H12^iv	2.46 (3)
C6···O2^v	3.386 (2)	H12···O11	2.555 (19)
C7···C2^viii	3.340 (3)	H12···O12^vii	2.69 (2)
C7···C12	3.362 (3)	H12···H11^vii	2.46 (3)
C7···C3^viii	3.599 (2)	H13···C18	2.612 (18)
C11···C2	3.600 (2)	H13···H15	2.33 (2)
C11···C1	3.586 (2)	H13···H16	2.27 (3)
C11···C13^ix	3.525 (2)	H13···H17	2.46 (3)
C12···C12^ix	3.485 (2)	H13···H18ⁱⁱ	2.38 (5)
C12···C7	3.362 (3)	H14···O11ⁱ	2.02 (3)
C12···C13^ix	3.571 (2)	H14···O13	2.26 (3)
C13···C12^ix	3.571 (2)	H15···H13	2.33 (2)
C13···C11^ix	3.525 (2)	H16···C12	2.71 (2)
C16···O12^vii	3.372 (2)	H16···H13	2.27 (3)
C17···C3	3.572 (2)	H16···C16^ix	2.82 (2)
C17···C2	3.349 (3)	H17···C12	2.822 (19)
C2···H8	2.79 (2)	H17···H13	2.46 (3)
C2···H9	2.76 (2)	H18···H13^v	2.38 (5)
C4···H19ⁱⁱⁱ	2.96 (3)	H19···O2ⁱ	2.78 (3)
C4···H5^vi	2.88 (3)	H19···C4ⁱ	2.96 (3)
C8···H4	2.579 (18)

C3—O3—C8	117.59 (12)	H5—C9—H6	111 (2)
C4—O2—H1	112.7 (19)	C8—C9—H5	110.3 (15)
C13—O13—C18	118.12 (12)	C12—C11—C17	119.54 (16)
C14—O12—H14	113 (2)	C16—C11—C17	120.59 (16)
C6—C1—C7	121.16 (15)	C12—C11—C16	119.86 (14)
C2—C1—C7	119.12 (15)	C11—C12—C13	120.38 (15)
C2—C1—C6	119.72 (14)	O13—C13—C14	114.08 (13)
C1—C2—C3	120.48 (14)	C12—C13—C14	119.18 (14)
C2—C3—C4	119.33 (13)	O13—C13—C12	126.72 (14)
O3—C3—C4	114.26 (12)	O12—C14—C15	118.78 (15)
O3—C3—C2	126.41 (13)	C13—C14—C15	120.14 (14)
O2—C4—C5	118.51 (14)	O12—C14—C13	121.08 (14)
C3—C4—C5	120.10 (13)	C14—C15—C16	120.17 (16)
O2—C4—C3	121.39 (13)	C11—C16—C15	120.24 (16)
C4—C5—C6	119.84 (16)	O11—C17—C11	124.5 (2)
C1—C6—C5	120.53 (15)	O13—C18—C19	106.81 (16)
O1—C7—C1	123.93 (18)	C11—C12—H13	117.8 (10)
O3—C8—C9	107.30 (15)	C13—C12—H13	121.8 (10)
C1—C2—H4	118.2 (10)	C14—C15—H11	117.1 (10)
C3—C2—H4	121.3 (10)	C16—C15—H11	122.7 (10)
C4—C5—H2	118.3 (10)	C11—C16—H12	117.4 (12)
C6—C5—H2	121.9 (10)	C15—C16—H12	122.4 (12)
C1—C6—H3	121.5 (12)	O11—C17—H15	120.6 (10)
C5—C6—H3	118.0 (12)	C11—C17—H15	114.8 (10)
C1—C7—H10	116.4 (10)	O13—C18—H16	106.9 (12)
O1—C7—H10	119.6 (10)	O13—C18—H17	107.3 (12)
O3—C8—H8	107.6 (12)	C19—C18—H16	113.3 (11)
C9—C8—H9	111.4 (11)	C19—C18—H17	112.5 (11)
O3—C8—H9	107.1 (12)	H16—C18—H17	109.6 (15)
C9—C8—H8	110.4 (14)	C18—C19—H18	103 (2)
H8—C8—H9	112.8 (17)	C18—C19—H19	107.0 (17)
C8—C9—H6	109.8 (16)	C18—C19—H20	110.5 (15)
C8—C9—H7	105.7 (17)	H18—C19—H19	113 (2)
H5—C9—H7	107 (2)	H18—C19—H20	111 (2)
H6—C9—H7	113 (2)	H19—C19—H20	112 (2)

C8—O3—C3—C4	179.15 (16)	C3—C4—C5—C6	0.3 (3)
C8—O3—C3—C2	−0.7 (3)	O2—C4—C5—C6	−179.73 (17)
C3—O3—C8—C9	−179.32 (17)	C4—C5—C6—C1	−0.4 (3)
C13—O13—C18—C19	−178.06 (17)	C16—C11—C12—C13	0.7 (3)
C18—O13—C13—C14	−176.92 (16)	C12—C11—C17—O11	179.41 (18)
C18—O13—C13—C12	4.4 (3)	C16—C11—C17—O11	0.5 (3)
C6—C1—C2—C3	−0.1 (2)	C17—C11—C16—C15	177.65 (17)
C7—C1—C6—C5	179.79 (17)	C12—C11—C16—C15	−1.2 (3)
C2—C1—C6—C5	0.3 (3)	C17—C11—C12—C13	−178.19 (16)
C2—C1—C7—O1	179.85 (18)	C11—C12—C13—O13	179.34 (16)
C7—C1—C2—C3	−179.64 (16)	C11—C12—C13—C14	0.8 (2)
C6—C1—C7—O1	0.3 (3)	O13—C13—C14—C15	179.53 (16)
C1—C2—C3—C4	0.0 (2)	C12—C13—C14—O12	177.97 (16)
C1—C2—C3—O3	179.87 (16)	C12—C13—C14—C15	−1.7 (2)
O3—C3—C4—O2	0.1 (2)	O13—C13—C14—O12	−0.8 (2)
C2—C3—C4—O2	179.89 (15)	C13—C14—C15—C16	1.2 (3)
O3—C3—C4—C5	−179.95 (16)	O12—C14—C15—C16	−178.48 (17)
C2—C3—C4—C5	−0.1 (2)	C14—C15—C16—C11	0.3 (3)

Symmetry codes: (i) x, y, z−1; (ii) x, −y+1/2, z+1/2; (iii) x, y, z+1; (iv) x, −y+3/2, z−1/2; (v) x, −y+1/2, z−1/2; (vi) −x, −y+1, −z+2; (vii) x, −y+3/2, z+1/2; (viii) −x, −y+1, −z+1; (ix) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1ⁱⁱⁱ	0.79 (3)	2.03 (3)	2.6951 (17)	142 (3)
O2—H1···O3	0.79 (3)	2.26 (3)	2.6619 (16)	112 (2)
O12—H14···O11ⁱ	0.81 (3)	2.02 (3)	2.7117 (19)	143 (3)
O12—H14···O13	0.81 (3)	2.26 (3)	2.6554 (18)	111 (2)

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

Experimental details

Crystal data
Chemical formula	C₉H₁₀O₃
M_r	166.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.7352 (6), 14.4140 (6), 8.7890 (4)
β (°)	100.742 (3)
V (Å³)	1709.55 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.50 × 0.50 × 0.40

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16625, 3934, 2581
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.155, 1.02
No. of reflections	3934
No. of parameters	297
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.20

Computer programs: SMART (Bruker, 2002), SAINT-Plus (Bruker, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1ⁱ	0.79 (3)	2.03 (3)	2.6951 (17)	142 (3)
O2—H1···O3	0.79 (3)	2.26 (3)	2.6619 (16)	112 (2)
O12—H14···O11ⁱⁱ	0.81 (3)	2.02 (3)	2.7117 (19)	143 (3)
O12—H14···O13	0.81 (3)	2.26 (3)	2.6554 (18)	111 (2)

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

Acknowledgements

The authors thank Professor Tao Zeng for invaluable advice.

References

Bruker (2002). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2003). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Ohta, T., Watanabe, M., Watanabe, K., Shirasu, Y. & Kada, T. (1986). Food Chem. Toxicol. 24, 51–54. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar