3,5-Bis(4-methoxy­phen­yl)-1H-1,2,4-triazole monohydrate

Wang, H.-Y.; Ma, J.-P.; Huang, R.-Q.; Dong, Y.-B.

doi:10.1107/S160053680901695X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1260

doi:10.1107/S160053680901695X

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3,5-Bis(4-methoxyphenyl)-1H-1,2,4-triazole monohydrate

Hai-Ying Wang,^a Jian-Ping Ma,^a Ru-Qi Huang ^a and Yu-Bin Dong ^a ^*

^aCollege of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014, People's Republic of China
^*Correspondence e-mail: yubindong@sdnu.edu.cn

(Received 24 April 2009; accepted 5 May 2009; online 14 May 2009)

In the title compound, C₁₆H₁₅N₃O₂·H₂O, the two benzene rings and the triazole ring lie almost in the same plane, the triazole ring forming dihedral angles of 5.07 (9) and 5.80 (8)° with the benzene rings. In the crystal, there are three relatively strong intermolecular O—H⋯N and N—H⋯O hydrogen bonds, which lead to the formation of a one-dimensional double chain running parallel to the a axis. Weak π—π interactions between the benzene rings of neighboring chains with a centroid–centroid distance of 3.893 (4) Å result in the formation of layers parallel to the ac plane.

Related literature

For the biological activity and pharmaceutical applications of compounds containing triazole subunits, see: Chai et al. (2009 ); Nadkarni et al. (2001 ); Zhan & Lou (2007 ). For triazole ring bond-length data, see; Claramunt et al. (2001 ); Zhou et al. (2001 ); John (1998 ).

Experimental

Crystal data

C₁₆H₁₅N₃O₂·H₂O
M_r = 299.33
Triclinic, $[P \overline 1]$
a = 6.9948 (18) Å
b = 11.125 (3) Å
c = 11.184 (3) Å
α = 110.603 (4)°
β = 107.932 (3)°
γ = 95.690 (4)°
V = 753.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.40 × 0.20 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
3854 measured reflections
2651 independent reflections
1993 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.134
S = 1.05
2651 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N1	0.97	1.96	2.902 (2)	164
N2—H2⋯O3ⁱ	0.86	1.90	2.753 (2)	170
O3—H3B⋯N3ⁱⁱ	0.96	1.97	2.885 (2)	159
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901695X/zl2201sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680901695X/zl2201Isup2.hkl

checkCIF report

Comment top

During the past decades, compounds containing triazole subunits have been intensively studied due to their diverse biological activities, such as antibacterial, antitumor, etc. and have become a central focus in the study of agricultural and medicinal chemicals (Chai et al., 2009; Nadkarni et al., 2001; Zhan et al., 2007). In a search for more effective antibacterial compounds, we have synthesized the title compound and determined its structure.

The molecular structure of the title compound is shown in Fig. 1. The two benzene rings and the triazole ring almost lie in the same plane. The corresponding dihedral angles of each benzene ring with the triazole ring are 5.07 (9) (between C2–C7 and N1–N3/C8/C9) and 5.80 (8)° (between N1–N3/C8/C9 and C10–C15), respectively. The bond lengths of the triazole ring are very similar to other 1H-1,2,4-triazole derivatives (Claramunt et al., 2001; Zhou et al., 2001). C8—N3 (1.365 (2) Å) and N1—N2 (1.359 (2) Å) are typical for carbon-nitrogen single bonds and nitrogen-nitrogen single bonds, and C8—N1 (1.323 (2) Å) and C9—N3 (1.330 (2) Å) correspond to typical carbon-nitrogen double bonds (John, 1998). C9—N2 (1.333 (2) Å) is a carbon-nitrogen single bond, but the bond length is markedly shorter than usual carbon-nitrogen single bonds and close to a double bond due to its conjugation with the C9—N3 double bond.

The packing of the molecules in the crystal structure is stabilized through N—H···O, O—H···O and π—π interactions. Water molecules act both as hydrogen-acceptor and as hydrogen-donor which leads to the formation of a one dimensional double chain running parallel to the a axis (Fig. 2, Table 1). The ring made up of C10 to C15 (with the centroid Cg1) is parallel to its symmetry related counterpart with a Cg1··· Cg1ⁱⁱⁱ distance of 3.893 (4) Å [symmetry code: (iii)-x, -y, -z]. Adjacent chains are linked via these intermolecular π—π interactions between the Cg1 rings to form a two-dimentional layer parallel to the ac plane (Fig. 3).

Related literature top

For the biological activity and pharmaceutical applications of compounds containing triazole subunits, see: Chai et al. (2009); Nadkarni et al. (2001); Zhan et al. (2007). For triazole ring bond-length data, see; Claramunt et al. (2001); Zhou et al. (2001); John (1998).

Experimental top

A mixture of 4-methoxyphenylmethylenemalononitrile (20 mmol), hydrazine dihydrochloride (20 mmol) and hydrazine hydrate (60 mmol) in ethylene glycol (10 ml) was heated to 403 K with stirring for 3–4 h. After cooling to room temperature, the reaction mixture was diluted with water (20 ml). The precipitate was filtered, washed with water, dried and purified by column chromatography on silica gel using CH₂Cl₂ as the eluent to afford a white solid after evaporation of the solvent. The white solid was dissolved in ethanol and colourless crystals of the title compound were obtained on slow evaporation of the solvent at room temperature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure, with atom labels and 30% probability displacement ellipsoids.
	Fig. 2. View of a one dimensional double chain of the title structure. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.
	Fig. 3. The crystal packing of the title compound via weak π—π interactions. The distance of centroids is 3.893 (4) Å (Dashed lines: hydrogen bonds; broken lines: π—π interactions.) [symmetry code: (iii) -x, -y, -z].

3,5-Bis(4-methoxyphenyl)-1H-1,2,4-triazole monohydrate top

Crystal data top

C₁₆H₁₅N₃O₂·H₂O	Z = 2
M_r = 299.33	F(000) = 316
Triclinic, P1	D_x = 1.319 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9948 (18) Å	Cell parameters from 1120 reflections
b = 11.125 (3) Å	θ = 2.2–24.0°
c = 11.184 (3) Å	µ = 0.09 mm⁻¹
α = 110.603 (4)°	T = 298 K
β = 107.932 (3)°	Block, colourless
γ = 95.690 (4)°	0.40 × 0.20 × 0.19 mm
V = 753.8 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	1993 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.016
Graphite monochromator	θ_max = 25.1°, θ_min = 2.0°
phi and ω scans	h = −4→8
3854 measured reflections	k = −13→11
2651 independent reflections	l = −12→13

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0708P)² + 0.0124P] where P = (F_o² + 2F_c²)/3
2651 reflections	(Δ/σ)_max = 0.001
201 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₆H₁₅N₃O₂·H₂O	γ = 95.690 (4)°
M_r = 299.33	V = 753.8 (3) Å³
Triclinic, P1	Z = 2
a = 6.9948 (18) Å	Mo Kα radiation
b = 11.125 (3) Å	µ = 0.09 mm⁻¹
c = 11.184 (3) Å	T = 298 K
α = 110.603 (4)°	0.40 × 0.20 × 0.19 mm
β = 107.932 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1993 reflections with I > 2σ(I)
3854 measured reflections	R_int = 0.016
2651 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.05	Δρ_max = 0.17 e Å⁻³
2651 reflections	Δρ_min = −0.25 e Å⁻³
201 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

	x	y	z	U_iso*/U_eq
C1	1.3626 (4)	0.5268 (3)	0.8502 (3)	0.0831 (8)
H1A	1.4171	0.4539	0.8091	0.125*
H1B	1.4672	0.5887	0.9349	0.125*
H1C	1.3199	0.5696	0.7886	0.125*
C2	1.0219 (3)	0.3942 (2)	0.7668 (2)	0.0493 (5)
C3	0.8500 (3)	0.3622 (2)	0.7965 (2)	0.0506 (5)
H3	0.8550	0.3978	0.8864	0.061*
C4	0.6729 (3)	0.27787 (19)	0.6928 (2)	0.0447 (5)
H4	0.5585	0.2571	0.7137	0.054*
C5	0.6599 (3)	0.22255 (18)	0.55736 (19)	0.0394 (5)
C6	0.8338 (3)	0.2549 (2)	0.5307 (2)	0.0524 (6)
H6	0.8292	0.2193	0.4409	0.063*
C7	1.0141 (3)	0.3388 (2)	0.6341 (2)	0.0578 (6)
H7	1.1300	0.3576	0.6138	0.069*
C8	0.4703 (3)	0.13404 (18)	0.44671 (18)	0.0368 (4)
C9	0.2616 (3)	0.00131 (18)	0.24816 (19)	0.0379 (5)
C10	0.1682 (3)	−0.08505 (18)	0.10190 (19)	0.0393 (5)
C11	0.2847 (3)	−0.0918 (2)	0.0197 (2)	0.0519 (6)
H11	0.4199	−0.0417	0.0587	0.062*
C12	0.2030 (3)	−0.1712 (2)	−0.1177 (2)	0.0598 (6)
H12	0.2828	−0.1741	−0.1711	0.072*
C13	0.0040 (3)	−0.2468 (2)	−0.1776 (2)	0.0503 (5)
C14	−0.1137 (3)	−0.2420 (2)	−0.0979 (2)	0.0539 (6)
H14	−0.2481	−0.2932	−0.1372	0.065*
C15	−0.0313 (3)	−0.1610 (2)	0.0403 (2)	0.0499 (5)
H15	−0.1121	−0.1576	0.0932	0.060*
C16	−0.2664 (4)	−0.4015 (2)	−0.3827 (2)	0.0745 (8)
H16A	−0.2851	−0.4629	−0.3425	0.112*
H16B	−0.2915	−0.4491	−0.4783	0.112*
H16C	−0.3617	−0.3455	−0.3735	0.112*
N1	0.2943 (2)	0.10899 (16)	0.46420 (16)	0.0437 (4)
N2	0.1636 (2)	0.02456 (16)	0.33612 (16)	0.0424 (4)
H2	0.0354	−0.0092	0.3148	0.051*
N3	0.4569 (2)	0.06990 (15)	0.31449 (15)	0.0404 (4)
O1	−0.0613 (2)	−0.32325 (16)	−0.31464 (15)	0.0726 (5)
O2	1.1911 (2)	0.48023 (16)	0.87639 (15)	0.0693 (5)
O3	0.2326 (2)	0.08148 (15)	0.69915 (14)	0.0540 (4)
H3A	0.2339	0.1008	0.6215	0.100*
H3B	0.3314	0.0294	0.7142	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0486 (14)	0.087 (2)	0.079 (2)	−0.0039 (13)	0.0166 (13)	0.0062 (16)
C2	0.0446 (12)	0.0498 (13)	0.0414 (12)	0.0095 (10)	0.0117 (10)	0.0088 (10)
C3	0.0611 (14)	0.0521 (13)	0.0338 (12)	0.0116 (10)	0.0194 (10)	0.0106 (10)
C4	0.0481 (12)	0.0474 (12)	0.0392 (12)	0.0092 (9)	0.0215 (9)	0.0139 (10)
C5	0.0434 (11)	0.0407 (11)	0.0372 (11)	0.0122 (9)	0.0182 (9)	0.0157 (9)
C6	0.0494 (13)	0.0623 (14)	0.0362 (12)	0.0052 (10)	0.0205 (10)	0.0075 (10)
C7	0.0457 (12)	0.0662 (15)	0.0519 (14)	0.0043 (11)	0.0238 (11)	0.0103 (12)
C8	0.0401 (10)	0.0403 (11)	0.0340 (11)	0.0121 (8)	0.0173 (8)	0.0157 (9)
C9	0.0373 (10)	0.0439 (11)	0.0381 (11)	0.0114 (9)	0.0175 (9)	0.0191 (10)
C10	0.0417 (11)	0.0419 (11)	0.0351 (11)	0.0075 (9)	0.0147 (9)	0.0166 (9)
C11	0.0477 (12)	0.0585 (14)	0.0380 (12)	−0.0078 (10)	0.0166 (10)	0.0109 (11)
C12	0.0638 (15)	0.0636 (15)	0.0438 (13)	−0.0072 (12)	0.0258 (11)	0.0130 (12)
C13	0.0615 (14)	0.0427 (12)	0.0346 (12)	0.0000 (10)	0.0095 (10)	0.0123 (10)
C14	0.0437 (12)	0.0563 (14)	0.0495 (14)	−0.0016 (10)	0.0101 (10)	0.0170 (11)
C15	0.0397 (11)	0.0608 (14)	0.0475 (13)	0.0072 (10)	0.0173 (10)	0.0202 (11)
C16	0.0777 (17)	0.0606 (16)	0.0490 (15)	−0.0158 (13)	−0.0073 (12)	0.0160 (13)
N1	0.0420 (9)	0.0526 (10)	0.0366 (10)	0.0123 (8)	0.0178 (8)	0.0148 (8)
N2	0.0329 (8)	0.0539 (10)	0.0385 (10)	0.0071 (7)	0.0147 (7)	0.0160 (8)
N3	0.0370 (9)	0.0472 (10)	0.0338 (9)	0.0064 (7)	0.0148 (7)	0.0124 (8)
O1	0.0834 (12)	0.0678 (11)	0.0387 (10)	−0.0165 (9)	0.0129 (8)	0.0074 (8)
O2	0.0503 (9)	0.0764 (12)	0.0499 (10)	−0.0021 (8)	0.0085 (7)	0.0033 (9)
O3	0.0439 (8)	0.0746 (10)	0.0513 (9)	0.0170 (7)	0.0265 (7)	0.0255 (8)

Geometric parameters (Å, º) top

C1—O2	1.412 (3)	C9—C10	1.462 (3)
C1—H1A	0.9600	C10—C15	1.379 (3)
C1—H1B	0.9600	C10—C11	1.393 (3)
C1—H1C	0.9600	C11—C12	1.368 (3)
C2—O2	1.370 (2)	C11—H11	0.9300
C2—C7	1.373 (3)	C12—C13	1.375 (3)
C2—C3	1.389 (3)	C12—H12	0.9300
C3—C4	1.370 (3)	C13—O1	1.362 (2)
C3—H3	0.9300	C13—C14	1.380 (3)
C4—C5	1.390 (3)	C14—C15	1.379 (3)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.381 (3)	C15—H15	0.9300
C5—C8	1.461 (3)	C16—O1	1.418 (3)
C6—C7	1.381 (3)	C16—H16A	0.9600
C6—H6	0.9300	C16—H16B	0.9600
C7—H7	0.9300	C16—H16C	0.9600
C8—N1	1.323 (2)	N1—N2	1.359 (2)
C8—N3	1.365 (2)	N2—H2	0.8600
C9—N3	1.330 (2)	O3—H3A	0.9678
C9—N2	1.333 (2)	O3—H3B	0.9583

O2—C1—H1A	109.5	C15—C10—C9	123.15 (18)
O2—C1—H1B	109.5	C11—C10—C9	119.01 (17)
H1A—C1—H1B	109.5	C12—C11—C10	120.85 (18)
O2—C1—H1C	109.5	C12—C11—H11	119.6
H1A—C1—H1C	109.5	C10—C11—H11	119.6
H1B—C1—H1C	109.5	C11—C12—C13	120.7 (2)
O2—C2—C7	124.66 (19)	C11—C12—H12	119.7
O2—C2—C3	115.73 (19)	C13—C12—H12	119.7
C7—C2—C3	119.61 (19)	O1—C13—C12	115.9 (2)
C4—C3—C2	119.73 (19)	O1—C13—C14	124.71 (19)
C4—C3—H3	120.1	C12—C13—C14	119.4 (2)
C2—C3—H3	120.1	C15—C14—C13	119.77 (19)
C3—C4—C5	121.72 (19)	C15—C14—H14	120.1
C3—C4—H4	119.1	C13—C14—H14	120.1
C5—C4—H4	119.1	C10—C15—C14	121.47 (19)
C6—C5—C4	117.40 (18)	C10—C15—H15	119.3
C6—C5—C8	120.93 (17)	C14—C15—H15	119.3
C4—C5—C8	121.67 (17)	O1—C16—H16A	109.5
C7—C6—C5	121.7 (2)	O1—C16—H16B	109.5
C7—C6—H6	119.2	H16A—C16—H16B	109.5
C5—C6—H6	119.2	O1—C16—H16C	109.5
C2—C7—C6	119.84 (19)	H16A—C16—H16C	109.5
C2—C7—H7	120.1	H16B—C16—H16C	109.5
C6—C7—H7	120.1	C8—N1—N2	102.97 (15)
N1—C8—N3	113.34 (16)	C9—N2—N1	110.53 (15)
N1—C8—C5	123.47 (16)	C9—N2—H2	124.7
N3—C8—C5	123.19 (16)	N1—N2—H2	124.7
N3—C9—N2	109.15 (17)	C9—N3—C8	104.00 (15)
N3—C9—C10	125.62 (17)	C13—O1—C16	118.50 (18)
N2—C9—C10	125.23 (17)	C2—O2—C1	118.09 (18)
C15—C10—C11	117.84 (18)	H3A—O3—H3B	107.8

O2—C2—C3—C4	179.32 (17)	C11—C12—C13—O1	−179.37 (19)
C7—C2—C3—C4	−1.4 (3)	C11—C12—C13—C14	0.1 (3)
C2—C3—C4—C5	0.1 (3)	O1—C13—C14—C15	179.8 (2)
C3—C4—C5—C6	0.5 (3)	C12—C13—C14—C15	0.4 (3)
C3—C4—C5—C8	−179.20 (17)	C11—C10—C15—C14	0.4 (3)
C4—C5—C6—C7	0.1 (3)	C9—C10—C15—C14	−179.59 (18)
C8—C5—C6—C7	179.80 (18)	C13—C14—C15—C10	−0.7 (3)
O2—C2—C7—C6	−178.80 (19)	N3—C8—N1—N2	0.0 (2)
C3—C2—C7—C6	2.0 (3)	C5—C8—N1—N2	179.44 (16)
C5—C6—C7—C2	−1.3 (3)	N3—C9—N2—N1	−0.6 (2)
C6—C5—C8—N1	−173.76 (19)	C10—C9—N2—N1	179.86 (16)
C4—C5—C8—N1	6.0 (3)	C8—N1—N2—C9	0.35 (19)
C6—C5—C8—N3	5.6 (3)	N2—C9—N3—C8	0.6 (2)
C4—C5—C8—N3	−174.69 (17)	C10—C9—N3—C8	−179.88 (17)
N3—C9—C10—C15	175.33 (18)	N1—C8—N3—C9	−0.4 (2)
N2—C9—C10—C15	−5.2 (3)	C5—C8—N3—C9	−179.81 (16)
N3—C9—C10—C11	−4.6 (3)	C12—C13—O1—C16	−178.8 (2)
N2—C9—C10—C11	174.80 (18)	C14—C13—O1—C16	1.8 (3)
C15—C10—C11—C12	0.1 (3)	C7—C2—O2—C1	7.2 (3)
C9—C10—C11—C12	−179.88 (19)	C3—C2—O2—C1	−173.6 (2)
C10—C11—C12—C13	−0.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N1	0.97	1.96	2.902 (2)	164
N2—H2···O3ⁱ	0.86	1.90	2.753 (2)	170
O3—H3B···N3ⁱⁱ	0.96	1.97	2.885 (2)	159

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅N₃O₂·H₂O
M_r	299.33
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.9948 (18), 11.125 (3), 11.184 (3)
α, β, γ (°)	110.603 (4), 107.932 (3), 95.690 (4)
V (Å³)	753.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.20 × 0.19

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3854, 2651, 1993
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.134, 1.05
No. of reflections	2651
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.25

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N1	0.97	1.96	2.902 (2)	163.7
N2—H2···O3ⁱ	0.86	1.90	2.753 (2)	169.6
O3—H3B···N3ⁱⁱ	0.96	1.97	2.885 (2)	158.9

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

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant Nos. 20871076 and 20671060), the PhD Programs Foundation of the Ministry of Education of China (grant No. 200804450001) and the Shandong Natural Science Foundation (grant No. JQ200803) for support.

References

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chai, X.-Y., Zhang, J., Yu, S.-C., Hu, H.-G., Zou, Y., Zhao, Q.-J., Dan, Z.-G., Zhang, D.-Z. & Wu, Q.-Y. (2009). Bioorg. Med. Chem. Lett. 19, 1811–1814. Web of Science CrossRef PubMed CAS Google Scholar
Claramunt, R. M., Lopez, C., Angeles, G. M., Dolores, O. M., Rosario, T. M., Pinilla, E., Alarcon, S. H., Alkorta, I. & Elguero, J. (2001). New J. Chem. 25, 1061–1068. Web of Science CSD CrossRef CAS Google Scholar
John, A. D. (1998). Lang's Handbook of Chemistry, Vol. 4, pp. 39–41. New York: McGraw-Hill. Google Scholar
Nadkarni, B. A., Kamat, V. R. & Khadse, B. G. (2001). Arzneim. Forsch. 51,569–573. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhan, T.-R. & Lou, H.-X. (2007). Carbohydr. Res. 342, 865–869. Web of Science CrossRef PubMed CAS Google Scholar
Zhou, X. J., Kovalev, E. G., Klug, J. T. & Khodorkovsky, V. (2001). Org. Lett. 3, 1725–1727. Web of Science CSD CrossRef PubMed CAS Google Scholar