2,4,5-Trimeth­oxy­benzaldehyde monohydrate

Abdullah M Asiri; Salman A Khan; M Nawaz Tahir

doi:10.1107/S160053681004794X

. 2010 Nov 24;66(Pt 12):o3270. doi: 10.1107/S160053681004794X

2,4,5-Trimethoxybenzaldehyde monohydrate

Abdullah M Asiri ^a,^b, Salman A Khan ^b, M Nawaz Tahir ^c,^*

PMCID: PMC3011575 PMID: 21589553

Abstract

In the title compound, C₁₀H₁₂O₄·H₂O, the 2,4,5-trimethoxybenzaldehyde molecule is almost planar (rms deviation = 0.0183 Å). There is an R ₁ ²(5) ring motif due to O—H⋯O hydrogen bonding. In the crystal, the molecules are stabilized in the form of one-dimensional polymeric chains extending along [010] due to O—H⋯O hydrogen bonding with adjacent water molecules. The H atoms involved in intermolecular hydrogen bonding are disordered over two sets of sites of equal occupancy.

Related literature

For related background and related structures, see: Asiri et al. (2010a ▶,b ▶), Hussain et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₀H₁₂O₄·H₂O
M _r = 214.21
Monoclinic,
a = 18.084 (5) Å
b = 4.2456 (10) Å
c = 14.600 (4) Å
β = 108.290 (9)°
V = 1064.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.22 × 0.10 × 0.08 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.992, T _max = 0.995
8287 measured reflections
1915 independent reflections
983 reflections with I > 2σ(I)
R _int = 0.066

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.212
S = 1.05
1915 reflections
148 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Bruno et al., 2002 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681004794X/dn2621sup1.cif

e-66-o3270-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004794X/dn2621Isup2.hkl

e-66-o3270-Isup2.hkl^{(92.3KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯O2	0.85 (4)	2.54 (5)	3.181 (5)	133 (4)
O5—H51⋯O3	0.85 (4)	2.19 (4)	3.006 (5)	160 (4)
O5—H52⋯O5ⁱ	0.83 (10)	1.89 (10)	2.710 (6)	174 (19)
O5—H53⋯O5ⁱⁱ	0.86 (10)	1.86 (10)	2.714 (6)	169 (7)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors would like to thank the Chemistry Department, King Abdul Aziz University, Jeddah, Saudi Arabia for providing research facilities and for the financial support of this work via grant No. (3–045/430).

supplementary crystallographic information

Comment

The crystal structure of (II) i.e., (E)-1-(2,5-dimethyl-3-thienyl)-3- (2,4,5-trimethoxyphenyl)prop-2-en-1-one (Asiri et al., 2010a), (III) i.e., 3,4-dimethyl-N-(2,4,5-trimethoxybenzylidene)-1,2-isoxazol-5-amine (Asiri et al., 2010b) and (IV) i.e., 2,3-Dimethyl-N-[(E)-2,4,5 -trimethoxybenzylidene]aniline (Hussain et al., 2010) have been published which contain the aldehyde moiety. The title compound (I, Fig. 1) is being reported here in which the aldehyde has reacted with water instead of aniline.

In (I), the 2,4,5-trimethoxybenzaldehyde is planar with r. m. s. deviation of 0.0183 Å. One of the H-atoms of water molecule is disordered over two set of sites with equal occupancy ratio. The non-disordered H-atom of H₂O makes H-bonding with adjacent two methoxy groups through O—H···O type and complete an R₁²(5) ring motif (Bernstein et al., 1995). The disordered H-atoms of H₂O makes H-bonding of O—H···O type with adjacent water molecules (Table 1, Fig. 2). Due to these H-bondings molecules are stabilized in the form of one dimensional polymeric chains extending along the b axis i.e [010]. There does not appear any appreciable π interaction.

Experimental

A mixture of 2,4,5-methoxy benzaldehyde (0.50 g, 2.5 mmol) and 4H-[1,2,4] Triazol-3-ylamine (0.21 g, 2.5 mmol) in ethanol (15 ml) was refluxed for 5 h with stirring to give a light yellow precipitate. This material was filtered off and washed with ethanol to give the starting aldehyde coordinated to water. m.p. 376 K