2,4,5-Trimeth­oxy­benzaldehyde monohydrate

Asiri, A.M.; Khan, S.A.; Tahir, M.N.

doi:10.1107/S160053681004794X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3270

https://doi.org/10.1107/S160053681004794X

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2,4,5-Trimethoxybenzaldehyde monohydrate

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

^aThe Center of Excellence for Advanced Materials Research, King Abdul Aziz University, Jeddah 21589, PO Box 80203, Saudi Arabia, ^bDepartment of Chemistry, Faculty of Science, King Abdul Aziz University, Jeddah 21589, PO Box 80203, Saudi Arabia, and ^cDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 7 November 2010; accepted 17 November 2010; online 24 November 2010)

In the title compound, C₁₀H₁₂O₄·H₂O, the 2,4,5-trimethoxybenzaldehyde molecule is almost planar (rms deviation = 0.0183 Å). There is an R₁²(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, P 2₁ /c
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[F² > 2σ(F²)] = 0.060
wR(F²) = 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

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

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004794X/dn2621Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

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 top

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

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown as small spheres of arbitrary radii. The dotted lines represent the intramolecular H-bondings or bonds of disordered H-atoms.
	Fig. 2. Partial packing view showing the polymeric chains extending along the b axis.

2,4,5-Trimethoxybenzaldehyde monohydrate top

Crystal data top

C₁₀H₁₂O₄·H₂O	F(000) = 456
M_r = 214.21	D_x = 1.337 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 983 reflections
a = 18.084 (5) Å	θ = 2.4–25.3°
b = 4.2456 (10) Å	µ = 0.11 mm⁻¹
c = 14.600 (4) Å	T = 296 K
β = 108.290 (9)°	Needle, colourless
V = 1064.3 (5) Å³	0.22 × 0.10 × 0.08 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	1915 independent reflections
Radiation source: fine-focus sealed tube	983 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
Detector resolution: 8.20 pixels mm^-1	θ_max = 25.3°, θ_min = 2.4°
ω scans	h = −21→21
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −3→5
T_min = 0.992, T_max = 0.995	l = −17→17
8287 measured reflections

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.212	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0973P)² + 0.249P] where P = (F_o² + 2F_c²)/3
1915 reflections	(Δ/σ)_max < 0.001
148 parameters	Δρ_max = 0.18 e Å⁻³
3 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₀H₁₂O₄·H₂O	V = 1064.3 (5) Å³
M_r = 214.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.084 (5) Å	µ = 0.11 mm⁻¹
b = 4.2456 (10) Å	T = 296 K
c = 14.600 (4) Å	0.22 × 0.10 × 0.08 mm
β = 108.290 (9)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	1915 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	983 reflections with I > 2σ(I)
T_min = 0.992, T_max = 0.995	R_int = 0.066
8287 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	3 restraints
wR(F²) = 0.212	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.18 e Å⁻³
1915 reflections	Δρ_min = −0.22 e Å⁻³
148 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 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	Occ. (<1)
O1	0.08087 (15)	0.7631 (7)	0.1135 (2)	0.0705 (11)
O2	0.33240 (14)	0.6231 (6)	0.35470 (16)	0.0572 (9)
O3	0.38101 (14)	0.2960 (6)	0.23792 (17)	0.0588 (9)
O4	0.14718 (16)	0.2497 (8)	−0.0759 (2)	0.0873 (14)
C1	0.1290 (2)	0.4010 (10)	−0.0160 (3)	0.0697 (16)
C2	0.1803 (2)	0.4721 (8)	0.0809 (2)	0.0501 (12)
C3	0.1560 (2)	0.6509 (8)	0.1459 (3)	0.0511 (12)
C4	0.2054 (2)	0.7063 (8)	0.2389 (3)	0.0480 (12)
C5	0.2800 (2)	0.5845 (7)	0.2667 (2)	0.0452 (11)
C6	0.3059 (2)	0.4044 (8)	0.2018 (2)	0.0454 (12)
C7	0.2562 (2)	0.3514 (8)	0.1105 (3)	0.0479 (12)
C8	0.0523 (2)	0.9331 (10)	0.1787 (3)	0.0740 (16)
C9	0.3107 (2)	0.8019 (9)	0.4243 (3)	0.0635 (16)
C10	0.4117 (2)	0.1230 (9)	0.1747 (3)	0.0636 (14)
O5	0.4918 (2)	0.2497 (10)	0.4398 (3)	0.0985 (18)
H1	0.07829	0.47778	−0.03301	0.0837*
H4	0.18830	0.82431	0.28205	0.0578*
H7	0.27321	0.23288	0.06748	0.0575*
H8A	0.08262	1.12102	0.19862	0.1111*
H8B	0.05607	0.80482	0.23412	0.1111*
H8C	−0.00117	0.98883	0.14757	0.1111*
H9A	0.26526	0.71063	0.43414	0.0950*
H9B	0.29959	1.01451	0.40177	0.0950*
H9C	0.35269	0.80171	0.48406	0.0950*
H10A	0.41096	0.25222	0.12043	0.0949*
H10B	0.38052	−0.06151	0.15245	0.0949*
H10C	0.46429	0.06141	0.20837	0.0949*
H51	0.452 (2)	0.274 (13)	0.390 (3)	0.1180*
H52	0.498 (9)	0.09 (2)	0.474 (9)	0.1180*	0.500
H53	0.492 (9)	0.42 (2)	0.472 (9)	0.1180*	0.500

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0409 (16)	0.094 (2)	0.0703 (19)	0.0102 (14)	0.0084 (14)	−0.0162 (15)
O2	0.0539 (16)	0.0718 (16)	0.0397 (14)	0.0065 (12)	0.0060 (13)	−0.0050 (12)
O3	0.0494 (16)	0.0691 (17)	0.0519 (16)	0.0141 (13)	0.0071 (13)	−0.0061 (12)
O4	0.056 (2)	0.140 (3)	0.0593 (19)	0.0016 (17)	0.0087 (16)	−0.0300 (19)
C1	0.047 (2)	0.095 (3)	0.059 (3)	0.000 (2)	0.005 (2)	−0.012 (2)
C2	0.043 (2)	0.058 (2)	0.048 (2)	−0.0036 (18)	0.0126 (18)	0.0013 (18)
C3	0.038 (2)	0.058 (2)	0.056 (2)	−0.0028 (17)	0.0127 (19)	0.0030 (18)
C4	0.045 (2)	0.053 (2)	0.045 (2)	0.0003 (17)	0.0127 (18)	−0.0022 (16)
C5	0.047 (2)	0.0455 (19)	0.040 (2)	−0.0056 (17)	0.0092 (18)	0.0024 (15)
C6	0.040 (2)	0.050 (2)	0.045 (2)	0.0006 (16)	0.0115 (18)	0.0065 (16)
C7	0.044 (2)	0.055 (2)	0.047 (2)	−0.0051 (17)	0.0177 (18)	−0.0022 (17)
C8	0.045 (2)	0.080 (3)	0.095 (3)	0.005 (2)	0.019 (2)	−0.011 (2)
C9	0.068 (3)	0.068 (3)	0.050 (2)	0.000 (2)	0.012 (2)	−0.0073 (19)
C10	0.052 (2)	0.067 (2)	0.069 (3)	0.0106 (19)	0.015 (2)	−0.005 (2)
O5	0.074 (2)	0.124 (4)	0.083 (3)	0.002 (3)	0.004 (2)	0.020 (2)

Geometric parameters (Å, º) top

O1—C3	1.376 (5)	C5—C6	1.407 (5)
O1—C8	1.415 (5)	C6—C7	1.372 (5)
O2—C5	1.346 (4)	C1—H1	0.9300
O2—C9	1.419 (5)	C4—H4	0.9300
O3—C6	1.373 (4)	C7—H7	0.9300
O3—C10	1.422 (5)	C8—H8A	0.9600
O4—C1	1.211 (5)	C8—H8B	0.9600
O5—H53	0.86 (10)	C8—H8C	0.9600
O5—H51	0.85 (4)	C9—H9C	0.9600
O5—H52	0.83 (10)	C9—H9A	0.9600
C1—C2	1.459 (5)	C9—H9B	0.9600
C2—C3	1.390 (5)	C10—H10A	0.9600
C2—C7	1.400 (5)	C10—H10B	0.9600
C3—C4	1.391 (6)	C10—H10C	0.9600
C4—C5	1.382 (5)

O2···O3	2.559 (4)	H4···C9	2.5200
O2···O5	3.181 (5)	H4···H9B	2.3600
O3···O5	3.006 (5)	H4···H9A	2.2700
O3···O2	2.559 (4)	H4···C8	2.4900
O5···O5ⁱ	2.714 (6)	H7···O4	2.5700
O5···C10ⁱⁱ	3.191 (6)	H7···C10	2.5500
O5···O3	3.006 (5)	H7···H10A	2.3700
O5···O5ⁱⁱⁱ	2.710 (6)	H7···H10B	2.3100
O5···O2	3.181 (5)	H8A···C3^vii	2.8400
O1···H1	2.4500	H8A···C4	2.7500
O2···H51	2.54 (5)	H8A···H4	2.2900
O2···H9B^iv	2.7900	H8B···C4	2.7100
O3···H10Cⁱⁱ	2.8900	H8B···C8^xii	3.0800
O3···H51	2.19 (4)	H8B···H4	2.2700
O4···H9A^v	2.8600	H8C···O4^vi	2.7100
O4···H7	2.5700	H8C···C1^vi	3.0000
O4···H8C^vi	2.7100	H9A···H4	2.2700
O5···H9Cⁱ	2.6900	H9A···C4	2.7100
O5···H10Cⁱⁱ	2.8500	H9A···O4^xiii	2.8600
O5···H52ⁱⁱⁱ	1.89 (10)	H9B···C4	2.7800
O5···H53ⁱ	1.86 (11)	H9B···O2^vii	2.7900
C4···C7^vii	3.597 (5)	H9B···H4	2.3600
C7···C4^iv	3.597 (5)	H9B···C5^vii	3.0700
C7···C9^viii	3.494 (6)	H9C···O5ⁱ	2.6900
C9···C7^ix	3.494 (6)	H9C···H10B^xiii	2.5600
C10···O5^x	3.191 (6)	H10A···H7	2.3700
C1···H8C^vi	3.0000	H10A···C7	2.7900
C3···H8A^iv	2.8400	H10B···C6^iv	2.8400
C4···H8B	2.7100	H10B···H9C^v	2.5600
C4···H9A	2.7100	H10B···H7	2.3100
C4···H9B	2.7800	H10B···C7	2.7600
C4···H8A	2.7500	H10C···O5^x	2.8500
C5···H9B^iv	3.0700	H10C···O3^x	2.8900
C6···H10B^vii	2.8400	H10C···H10Cⁱⁱ	2.5800
C7···H10B	2.7600	H10C···C10^x	3.0000
C7···H10A	2.7900	H10C···H10C^x	2.5800
C8···H8B^xi	3.0800	H51···O2	2.54 (5)
C8···H4	2.4900	H51···O3	2.19 (4)
C9···H4	2.5200	H51···C10	3.06 (4)
C10···H7	2.5500	H51···H52ⁱⁱⁱ	2.45 (12)
C10···H10Cⁱⁱ	3.0000	H51···H53ⁱ	2.34 (13)
C10···H51	3.06 (4)	H52···O5ⁱⁱⁱ	1.89 (10)
H1···O1	2.4500	H52···H51ⁱⁱⁱ	2.45 (12)
H4···H8A	2.2900	H53···O5ⁱ	1.86 (10)
H4···H8B	2.2700	H53···H51ⁱ	2.34 (12)

C3—O1—C8	118.4 (3)	C3—C4—H4	120.00
C5—O2—C9	118.6 (3)	C5—C4—H4	120.00
C6—O3—C10	117.7 (3)	C6—C7—H7	119.00
H52—O5—H53	112 (10)	C2—C7—H7	119.00
H51—O5—H52	122 (10)	O1—C8—H8A	109.00
H51—O5—H53	103 (10)	O1—C8—H8B	109.00
O4—C1—C2	125.2 (4)	O1—C8—H8C	109.00
C3—C2—C7	118.6 (3)	H8B—C8—H8C	109.00
C1—C2—C3	122.3 (3)	H8A—C8—H8B	109.00
C1—C2—C7	119.1 (3)	H8A—C8—H8C	109.00
O1—C3—C2	116.4 (3)	O2—C9—H9B	109.00
O1—C3—C4	122.6 (3)	H9A—C9—H9C	110.00
C2—C3—C4	121.0 (3)	O2—C9—H9C	109.00
C3—C4—C5	119.5 (3)	H9A—C9—H9B	110.00
C4—C5—C6	120.4 (3)	O2—C9—H9A	109.00
O2—C5—C6	115.2 (3)	H9B—C9—H9C	109.00
O2—C5—C4	124.4 (3)	O3—C10—H10C	110.00
C5—C6—C7	119.2 (3)	H10A—C10—H10C	109.00
O3—C6—C7	125.8 (3)	H10B—C10—H10C	109.00
O3—C6—C5	114.9 (3)	H10A—C10—H10B	109.00
C2—C7—C6	121.3 (3)	O3—C10—H10A	109.00
O4—C1—H1	117.00	O3—C10—H10B	109.00
C2—C1—H1	117.00

C8—O1—C3—C2	176.9 (3)	C1—C2—C7—C6	−178.2 (3)
C8—O1—C3—C4	−2.0 (5)	C3—C2—C7—C6	0.6 (5)
C9—O2—C5—C4	−0.4 (5)	O1—C3—C4—C5	179.6 (3)
C9—O2—C5—C6	−180.0 (3)	C2—C3—C4—C5	0.7 (5)
C10—O3—C6—C5	−177.6 (3)	C3—C4—C5—O2	−179.9 (3)
C10—O3—C6—C7	2.5 (5)	C3—C4—C5—C6	−0.3 (5)
O4—C1—C2—C3	179.2 (4)	O2—C5—C6—O3	−0.3 (4)
O4—C1—C2—C7	−2.1 (6)	O2—C5—C6—C7	179.7 (3)
C1—C2—C3—O1	−1.1 (5)	C4—C5—C6—O3	−179.9 (3)
C1—C2—C3—C4	177.9 (3)	C4—C5—C6—C7	0.1 (5)
C7—C2—C3—O1	−179.8 (3)	O3—C6—C7—C2	179.7 (3)
C7—C2—C3—C4	−0.8 (5)	C5—C6—C7—C2	−0.2 (5)

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

Hydrogen-bond geometry (Å, º) top

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···O5ⁱⁱⁱ	0.83 (10)	1.89 (10)	2.710 (6)	174 (19)
O5—H53···O5ⁱ	0.86 (10)	1.86 (10)	2.714 (6)	169 (7)

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂O₄·H₂O
M_r	214.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	18.084 (5), 4.2456 (10), 14.600 (4)
β (°)	108.290 (9)
V (Å³)	1064.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.22 × 0.10 × 0.08

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.992, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	8287, 1915, 983
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.212, 1.05
No. of reflections	1915
No. of parameters	148
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.22

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al., 2002), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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)

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

Acknowledgements

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).

References

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