organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

4-Hy­droxy­meth­yl-2-meth­oxy­phenol

aHenan University, Kaifeng 475004, People's Republic of China
*Correspondence e-mail: wqwang228@163.com

(Received 19 October 2009; accepted 19 October 2009; online 23 October 2009)

The title compound, C8H10O3, is close to planar (r.m.s. deviation = 0.042 Å) apart from the hydroxyl O atom [deviation = 1.285 (1) Å] and an intra­molecular O—H⋯O hydrogen bond occurs. In the crystal, inter­molecular O—H⋯O links lead to chains propagating in [001].

Related literature

For a related compound used as a food additive, see: Kumar et al. (2004[Kumar, S. S., Priyadarsini, K. I. & Sainis, K. B. (2004). J. Agric. Food Chem. 52, 139-145.]); Shaughnessy et al. (2001[Shaughnessy, D. T., Setzer, R. W. & DeMarini, D. M. (2001). Mutat. Res. 480-481, 55-69.]).

[Scheme 1]

Experimental

Crystal data
  • C8H10O3

  • Mr = 154.16

  • Monoclinic, P 21 /c

  • a = 9.8476 (6) Å

  • b = 6.1721 (4) Å

  • c = 15.4915 (7) Å

  • β = 126.877 (2)°

  • V = 753.19 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.29 × 0.11 × 0.07 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SAINT-Plus, SMART and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.]) Tmin = 0.971, Tmax = 0.993

  • 3996 measured reflections

  • 1475 independent reflections

  • 1249 reflections with I > 2σ(I)

  • Rint = 0.015

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.102

  • S = 1.05

  • 1475 reflections

  • 102 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1A⋯O2 0.82 2.31 2.6669 (16) 107
O1—H1A⋯O3i 0.82 1.96 2.7390 (16) 158
O3—H3B⋯O1ii 0.84 2.07 2.8666 (15) 158
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT-Plus, SMART and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus, SMART and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information


Comment top

4-hydroxy-3-methoxybenzaldehyde is one of the commonly used food additives. In recent years, it was discovered that 4-hydroxy-3-methoxybenzaldehyde has anti-oxidation (Kumar et al., 2004) and inhibition activity of gene mutation (Shaughnessy et al., 2001). But its activity is low. Therefore, preparing derivatives has been an active research area. Herein we report the crystal structure of the title compound (I).

In the structure of the title compound (I) (Fig.1), the S(6) ring of C(1)/C(2)/C(3)/C(4)/C(5)/C(6) in (I) is an aromatic ring. C(1)–O(1) [1.3702 (16) Å], C(6)–O(2)[1.3683 (16) Å], C(8)–O(2)[1.4181 (18) Å], and C(7)–O(3) [1.433 (2) Å] are typical for C–O single bonds.

In the crystal structure, these molecules are linked into infinite one-dimensional network by intermolecular O—H···O hydrogen bonds running along [100] (Fig. 2, Table 1).

Related literature top

For a related compound used as a food additive, see: Kumar et al. (2004); Shaughnessy et al. (2001).

Experimental top

4-Hydroxy-3-methoxybenzaldehyde (3.8 g, 25 mmol) was dissolved in methanol (40 ml) at 283 K. After stirring for 30 min, borohydride (0.94 g, 25 mmol) was added in reaction solution, slowly. After 4 h, the solution was quenched with water (150 ml), vacuum concentrated to remove methanol and the aqueous layer was extracted with chloroform, the combined organic extracts were washed, dried and evaporated under reduced pressure to give the crude product. Then purification by column chromatography and recrystallization from chloroform gave (I) as colourless plates (2.58 g, 67%).

Refinement top

H atoms were treated as riding, with C—H distances in the range of 0.93–0.97 Å and O—H distances of 0.85 Å, and were refined as riding with Uiso(H)=1.2Ueq(Cmethylene and C in phenyl ring) and Uiso(H)=1.5Ueq(O and (Cmethyl)).

Structure description top

4-hydroxy-3-methoxybenzaldehyde is one of the commonly used food additives. In recent years, it was discovered that 4-hydroxy-3-methoxybenzaldehyde has anti-oxidation (Kumar et al., 2004) and inhibition activity of gene mutation (Shaughnessy et al., 2001). But its activity is low. Therefore, preparing derivatives has been an active research area. Herein we report the crystal structure of the title compound (I).

In the structure of the title compound (I) (Fig.1), the S(6) ring of C(1)/C(2)/C(3)/C(4)/C(5)/C(6) in (I) is an aromatic ring. C(1)–O(1) [1.3702 (16) Å], C(6)–O(2)[1.3683 (16) Å], C(8)–O(2)[1.4181 (18) Å], and C(7)–O(3) [1.433 (2) Å] are typical for C–O single bonds.

In the crystal structure, these molecules are linked into infinite one-dimensional network by intermolecular O—H···O hydrogen bonds running along [100] (Fig. 2, Table 1).

For a related compound used as a food additive, see: Kumar et al. (2004); Shaughnessy et al. (2001).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. One-dimensional structure of (I) showing hydrogen bonds as dashed lines.
4-Hydroxymethyl-2-methoxyphenol top
Crystal data top
C8H10O3F(000) = 328
Mr = 154.16Dx = 1.359 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1768 reflections
a = 9.8476 (6) Åθ = 2.6–27.6°
b = 6.1721 (4) ŵ = 0.10 mm1
c = 15.4915 (7) ÅT = 293 K
β = 126.877 (2)°Plate, colorless
V = 753.19 (8) Å30.29 × 0.11 × 0.07 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
1475 independent reflections
Radiation source: fine-focus sealed tube1249 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
ω scansθmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 128
Tmin = 0.971, Tmax = 0.993k = 77
3996 measured reflectionsl = 1719
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.102 w = 1/[σ2(Fo2) + (0.0462P)2 + 0.2254P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1475 reflectionsΔρmax = 0.24 e Å3
102 parametersΔρmin = 0.19 e Å3
2 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.043 (6)
Crystal data top
C8H10O3V = 753.19 (8) Å3
Mr = 154.16Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.8476 (6) ŵ = 0.10 mm1
b = 6.1721 (4) ÅT = 293 K
c = 15.4915 (7) Å0.29 × 0.11 × 0.07 mm
β = 126.877 (2)°
Data collection top
Bruker SMART CCD
diffractometer
1475 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
1249 reflections with I > 2σ(I)
Tmin = 0.971, Tmax = 0.993Rint = 0.015
3996 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0372 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 1.05Δρmax = 0.24 e Å3
1475 reflectionsΔρmin = 0.19 e Å3
102 parameters
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
xyzUiso*/Ueq
O10.16947 (13)0.60312 (18)0.16129 (8)0.0462 (3)
H1A0.17270.49010.13470.069*
O20.35690 (14)0.26017 (19)0.27618 (8)0.0501 (3)
O30.16416 (15)0.1981 (2)0.52945 (9)0.0621 (4)
H3B0.06750.20670.46970.093*
C10.19570 (17)0.5586 (2)0.25692 (11)0.0352 (3)
C20.12924 (18)0.6933 (2)0.29368 (12)0.0407 (4)
H2A0.07040.81730.25500.049*
C30.14955 (19)0.6447 (2)0.38857 (12)0.0416 (4)
H3A0.10340.73610.41250.050*
C40.23753 (17)0.4625 (2)0.44737 (11)0.0383 (3)
C50.31075 (18)0.3308 (2)0.41213 (11)0.0394 (4)
H5A0.37340.21000.45240.047*
C60.29122 (17)0.3781 (2)0.31805 (11)0.0360 (3)
C70.2509 (2)0.3978 (3)0.54583 (12)0.0467 (4)
H7A0.36960.38230.60650.056*
H7B0.20260.51110.56320.056*
C80.4600 (2)0.0789 (3)0.33595 (13)0.0491 (4)
H8A0.49970.01280.29870.074*
H8B0.39480.02420.34350.074*
H8C0.55540.12560.40610.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0591 (7)0.0473 (6)0.0406 (6)0.0118 (5)0.0344 (5)0.0107 (5)
O20.0624 (7)0.0559 (7)0.0461 (6)0.0249 (5)0.0400 (6)0.0144 (5)
O30.0635 (7)0.0802 (9)0.0413 (6)0.0217 (7)0.0308 (6)0.0033 (6)
C10.0360 (7)0.0382 (7)0.0338 (7)0.0010 (6)0.0223 (6)0.0021 (6)
C20.0446 (8)0.0359 (8)0.0413 (8)0.0057 (6)0.0256 (7)0.0033 (6)
C30.0467 (8)0.0412 (8)0.0434 (8)0.0016 (6)0.0304 (7)0.0052 (6)
C40.0389 (7)0.0440 (8)0.0318 (7)0.0031 (6)0.0212 (6)0.0040 (6)
C50.0399 (7)0.0428 (8)0.0339 (7)0.0070 (6)0.0212 (6)0.0056 (6)
C60.0348 (7)0.0403 (8)0.0360 (7)0.0029 (6)0.0228 (6)0.0008 (6)
C70.0542 (9)0.0532 (10)0.0374 (8)0.0009 (7)0.0300 (7)0.0031 (7)
C80.0526 (9)0.0500 (9)0.0496 (9)0.0155 (7)0.0332 (8)0.0079 (7)
Geometric parameters (Å, º) top
O1—C11.3702 (16)C3—H3A0.9300
O1—H1A0.8200C4—C51.397 (2)
O2—C61.3683 (16)C4—C71.5041 (19)
O2—C81.4181 (18)C5—C61.3820 (19)
O3—C71.433 (2)C5—H5A0.9300
O3—H3B0.8416C7—H7A0.9700
C1—C21.375 (2)C7—H7B0.9700
C1—C61.3977 (19)C8—H8A0.9600
C2—C31.392 (2)C8—H8B0.9600
C2—H2A0.9300C8—H8C0.9600
C3—C41.378 (2)
C1—O1—H1A109.5C4—C5—H5A119.6
C6—O2—C8117.84 (11)O2—C6—C5125.55 (13)
C7—O3—H3B107.5O2—C6—C1114.85 (12)
O1—C1—C2119.92 (12)C5—C6—C1119.60 (13)
O1—C1—C6120.39 (12)O3—C7—C4111.63 (12)
C2—C1—C6119.68 (12)O3—C7—H7A109.3
C1—C2—C3120.32 (13)C4—C7—H7A109.3
C1—C2—H2A119.8O3—C7—H7B109.3
C3—C2—H2A119.8C4—C7—H7B109.3
C4—C3—C2120.58 (13)H7A—C7—H7B108.0
C4—C3—H3A119.7O2—C8—H8A109.5
C2—C3—H3A119.7O2—C8—H8B109.5
C3—C4—C5118.93 (13)H8A—C8—H8B109.5
C3—C4—C7121.65 (13)O2—C8—H8C109.5
C5—C4—C7119.38 (13)H8A—C8—H8C109.5
C6—C5—C4120.78 (13)H8B—C8—H8C109.5
C6—C5—H5A119.6
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O20.822.312.6669 (16)107
O1—H1A···O3i0.821.962.7390 (16)158
O3—H3B···O1ii0.842.072.8666 (15)158
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC8H10O3
Mr154.16
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)9.8476 (6), 6.1721 (4), 15.4915 (7)
β (°) 126.877 (2)
V3)753.19 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.29 × 0.11 × 0.07
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.971, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
3996, 1475, 1249
Rint0.015
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.102, 1.05
No. of reflections1475
No. of parameters102
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.19

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O20.822.312.6669 (16)107
O1—H1A···O3i0.821.962.7390 (16)158
O3—H3B···O1ii0.842.072.8666 (15)158
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y1/2, z+1/2.
 

References

First citationBruker (2001). SAINT-Plus, SMART and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.  Google Scholar
First citationKumar, S. S., Priyadarsini, K. I. & Sainis, K. B. (2004). J. Agric. Food Chem. 52, 139–145.  Web of Science CrossRef PubMed CAS Google Scholar
First citationShaughnessy, D. T., Setzer, R. W. & DeMarini, D. M. (2001). Mutat. Res. 480–481, 55–69.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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