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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page o2615
https://doi.org/10.1107/S1600536809039300

(E)-N′-(2,5-Di­meth­oxy­benzyl­­idene)-3,4-di­hydroxy­benzohydrazide monohydrate

Bin Xu,a Ling Hanb* and Qi-Hui Zhangc‡

aDepartment of Nutrition, Jilin Medical College, Jilin 132013, People's Republic of China, bLiao Ning Benxi Third Pharmaceuticals Co Ltd, Benxi 117004, People's Republic of China, and cCollege of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China
*Correspondence e-mail: jlbinxu@163.com

(Received 19 September 2009; accepted 28 September 2009; online 3 October 2009)

In the title compound, C16H16N2O5·H2O, the dihedral angle between the two benzene rings is 25.9 (1)°. Intra­molecular O—H⋯O and N—H⋯O hydrogen bonds are observed. In the crystal, the components are linked into a three-dimensional network by O—H⋯O and O—H⋯(O,O) hydrogen bonds.

Related literature

For related structures, see: Pu (2008[Pu, X.-H. (2008). Acta Cryst. E64, o1734.]); Wang et al. (2009[Wang, S.-Y., Yuan, L., Xu, L., Zhang, Z., Diao, Y.-P. & Lv, D.-C. (2009). Acta Cryst. E65, o1154.]). For reference structural data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C16H16N2O5·H2O

  • Mr = 334.32

  • Monoclinic, P 21 /c

  • a = 10.2573 (8) Å

  • b = 12.4199 (10) Å

  • c = 14.0042 (8) Å

  • β = 119.666 (4)°

  • V = 1550.2 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 295 K

  • 0.20 × 0.18 × 0.17 mm
Data collection

  • Siemens SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Siemens, 1996[Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.981

  • 7993 measured reflections

  • 2735 independent reflections

  • 2110 reflections with I > 2σ(I)

  • Rint = 0.060
Refinement

  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.098

  • S = 1.02

  • 2735 reflections

  • 220 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O3i 0.82 2.03 2.8384 (15) 168
O2—H2⋯O1 0.82 2.25 2.7014 (15) 115
O2—H2⋯O5i 0.82 2.43 3.0191 (15) 130
O6—H17⋯O2ii 0.85 2.06 2.9003 (15) 169
O6—H18⋯O3i 0.85 1.95 2.7837 (15) 165
N1—H1A⋯O6 0.86 2.16 2.8592 (17) 138
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809039300/hb5111sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039300/hb5111Isup2.hkl

checkCIF report


Comment top

Schiff base compounds have been of great interest for many years. These compounds play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular architectures (Pu, 2008). As a part of our on going investigation in this field we have determined the crystal structure of the title compound, (I).

The Schiff base molecule of the compound displays a trans configuration with respect to the C=N and C—N bonds(Fig. 1). All the bond lengths are within normal ranges (Allen et al., 1987), and are comparable to other Schiff base compounds containing 2,5-dimethoxybenzaldehyde (Wang et al., 2009). The dihedral angle between the two benzene rings is 25.9 (1)°. Intramolecular O—H···O and N—H···O hydrogen bonds are observed (Table 1). Molecules are linked into three-dimensional network by O—H···O hydrogen bonds (Fig. 2).

Related literature top

For related structures, see: Pu (2008); Wang et al. (2009). For reference structural data, see: Allen et al. (1987).

Experimental top

2,5-Dimethoxybenzaldehyde (0.1 mmol, 16.6 mg) and 3,4-dihydroxybenzohydrazide (0.1 mmol, 16.9 mg) were dissolved in a 95% ethanol solution (10 ml). The mixture was stirred at room temperature to give a clear colorless solution. Light yellow blocks of (I) were formed by gradual evaporation of the solvent over a period of six days at room temperature.

Refinement top

All H atoms were placed in geometrically idealized positions (C—H = 0.93–0.96 Å, O—H = 0.82–0.85 Å and N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(O).

Structure description top

Schiff base compounds have been of great interest for many years. These compounds play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular architectures (Pu, 2008). As a part of our on going investigation in this field we have determined the crystal structure of the title compound, (I).

The Schiff base molecule of the compound displays a trans configuration with respect to the C=N and C—N bonds(Fig. 1). All the bond lengths are within normal ranges (Allen et al., 1987), and are comparable to other Schiff base compounds containing 2,5-dimethoxybenzaldehyde (Wang et al., 2009). The dihedral angle between the two benzene rings is 25.9 (1)°. Intramolecular O—H···O and N—H···O hydrogen bonds are observed (Table 1). Molecules are linked into three-dimensional network by O—H···O hydrogen bonds (Fig. 2).

For related structures, see: Pu (2008); Wang et al. (2009). For reference structural data, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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
[Figure 1] Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. The dashed lines indicate hydrogen bonds.
[Figure 2] Fig. 2. The molecular packing of (I). Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in the hydrogen bonds have been omitted for clarity.
(E)-N'-(2,5-Dimethoxybenzylidene)-3,4-dihydroxybenzohydrazide monohydrate top
Crystal data top
C16H16N2O5·H2OF(000) = 704
Mr = 334.32Dx = 1.432 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2817 reflections
a = 10.2573 (8) Åθ = 2.3–28.0°
b = 12.4199 (10) ŵ = 0.11 mm−1
c = 14.0042 (8) ÅT = 295 K
β = 119.666 (4)°Block, light yellow
V = 1550.2 (2) Å30.20 × 0.18 × 0.17 mm
Z = 4
Data collection top
Siemens SMART CCD
diffractometer		2735 independent reflections
Radiation source: fine-focus sealed tube2110 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
ω scansθmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Siemens, 1996)		h = −12→10
Tmin = 0.978, Tmax = 0.981k = −14→14
7993 measured reflectionsl = −16→15
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)] = 0.036H-atom parameters constrained
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0472P)2 + 0.0836P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2735 reflectionsΔρmax = 0.30 e Å−3
220 parametersΔρmin = −0.15 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0092 (15)
Crystal data top
C16H16N2O5·H2OV = 1550.2 (2) Å3
Mr = 334.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.2573 (8) ŵ = 0.11 mm−1
b = 12.4199 (10) ÅT = 295 K
c = 14.0042 (8) Å0.20 × 0.18 × 0.17 mm
β = 119.666 (4)°
Data collection top
Siemens SMART CCD
diffractometer		2735 independent reflections
Absorption correction: multi-scan
(SADABS; Siemens, 1996)		2110 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.981Rint = 0.060
7993 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.02Δρmax = 0.30 e Å−3
2735 reflectionsΔρmin = −0.15 e Å−3
220 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
O10.29807 (12)0.63600 (8)0.00386 (8)0.0415 (3)
H10.34780.67630.05580.062*
O20.25882 (12)0.49266 (9)−0.15328 (8)0.0451 (3)
H20.24790.5582−0.15610.068*
O30.50018 (13)0.24912 (8)0.30247 (8)0.0462 (3)
O40.83630 (14)0.60874 (9)0.70864 (9)0.0516 (3)
O50.84768 (13)0.17847 (9)0.81326 (9)0.0554 (4)
O60.71520 (13)0.60032 (9)0.33312 (9)0.0469 (3)
H170.73550.57470.28570.070*
H180.65600.65300.30210.070*
N10.56517 (14)0.42030 (10)0.36286 (9)0.0374 (3)
H1A0.56580.48730.34770.045*
N20.62828 (14)0.38569 (10)0.47007 (10)0.0386 (3)
C10.43573 (16)0.38751 (11)0.16836 (11)0.0311 (4)
C20.39529 (16)0.49534 (12)0.14219 (11)0.0324 (4)
H2A0.40680.54310.19700.039*
C30.33846 (15)0.53178 (12)0.03578 (12)0.0306 (3)
C40.31715 (16)0.45885 (12)−0.04685 (11)0.0328 (4)
C50.35509 (17)0.35223 (13)−0.02211 (12)0.0380 (4)
H50.34080.3041−0.07730.046*
C60.41477 (17)0.31659 (12)0.08543 (12)0.0363 (4)
H60.44090.24450.10200.044*
C70.50232 (16)0.34597 (12)0.28220 (12)0.0336 (4)
C80.69125 (17)0.45828 (13)0.54315 (12)0.0378 (4)
H80.68790.53000.52300.045*
C90.76899 (16)0.42735 (13)0.65942 (11)0.0346 (4)
C100.84706 (17)0.50414 (13)0.74194 (12)0.0364 (4)
C110.92900 (17)0.46990 (14)0.84979 (12)0.0410 (4)
H110.98250.52000.90490.049*
C120.93298 (18)0.36251 (14)0.87737 (12)0.0429 (4)
H120.98990.34100.95030.051*
C130.85242 (18)0.28700 (13)0.79661 (12)0.0396 (4)
C140.77166 (17)0.32066 (13)0.68859 (12)0.0390 (4)
H140.71760.27020.63400.047*
C150.9048 (2)0.68888 (14)0.79085 (14)0.0512 (5)
H15A0.86010.68840.83700.077*
H15B0.89030.75820.75670.077*
H15C1.01020.67430.83440.077*
C160.9447 (2)0.13853 (17)0.92118 (15)0.0683 (6)
H16A1.04610.15940.94420.102*
H16B0.93820.06140.92100.102*
H16C0.91510.16780.97100.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0508 (7)0.0360 (6)0.0266 (6)0.0042 (5)0.0106 (5)0.0021 (5)
O20.0597 (8)0.0478 (7)0.0227 (6)0.0049 (5)0.0166 (6)0.0044 (5)
O30.0635 (8)0.0327 (6)0.0257 (6)−0.0063 (5)0.0093 (6)0.0017 (5)
O40.0685 (8)0.0415 (7)0.0295 (6)−0.0086 (6)0.0126 (6)−0.0060 (5)
O50.0657 (8)0.0467 (7)0.0324 (7)−0.0016 (6)0.0079 (6)0.0076 (5)
O60.0586 (8)0.0424 (7)0.0345 (6)0.0024 (5)0.0190 (6)0.0026 (5)
N10.0499 (8)0.0325 (7)0.0176 (6)−0.0026 (6)0.0075 (6)0.0025 (5)
N20.0463 (8)0.0408 (8)0.0196 (6)−0.0029 (6)0.0093 (6)0.0009 (6)
C10.0319 (8)0.0328 (8)0.0222 (7)−0.0040 (6)0.0084 (6)−0.0006 (6)
C20.0339 (8)0.0351 (8)0.0226 (8)−0.0032 (6)0.0097 (7)−0.0039 (6)
C30.0280 (8)0.0335 (8)0.0243 (8)0.0000 (6)0.0084 (6)0.0013 (6)
C40.0326 (8)0.0427 (9)0.0200 (8)−0.0026 (7)0.0107 (7)0.0008 (6)
C50.0471 (10)0.0385 (9)0.0254 (8)−0.0036 (7)0.0156 (7)−0.0065 (7)
C60.0429 (9)0.0322 (8)0.0277 (8)−0.0012 (7)0.0128 (7)−0.0007 (7)
C70.0361 (9)0.0337 (9)0.0238 (8)−0.0029 (6)0.0094 (7)−0.0008 (6)
C80.0433 (9)0.0373 (9)0.0265 (8)−0.0001 (7)0.0125 (7)−0.0012 (7)
C90.0335 (9)0.0432 (9)0.0216 (8)0.0009 (6)0.0095 (7)−0.0026 (6)
C100.0388 (9)0.0410 (9)0.0268 (8)−0.0007 (7)0.0143 (7)−0.0034 (7)
C110.0438 (10)0.0484 (10)0.0233 (8)−0.0048 (7)0.0109 (7)−0.0091 (7)
C120.0454 (10)0.0542 (11)0.0204 (8)0.0024 (8)0.0097 (7)0.0005 (7)
C130.0425 (10)0.0427 (10)0.0278 (8)0.0002 (7)0.0130 (7)0.0009 (7)
C140.0413 (9)0.0433 (10)0.0240 (8)−0.0017 (7)0.0098 (7)−0.0041 (7)
C150.0569 (11)0.0437 (10)0.0422 (10)−0.0060 (8)0.0162 (9)−0.0106 (8)
C160.0812 (15)0.0597 (13)0.0383 (11)0.0024 (10)0.0099 (10)0.0188 (9)
Geometric parameters (Å, º) top
O1—C31.3652 (17)C4—C51.375 (2)
O1—H10.8200C5—C61.388 (2)
O2—C41.3687 (16)C5—H50.9300
O2—H20.8198C6—H60.9300
O3—C71.2386 (17)C8—C91.466 (2)
O4—C101.3662 (19)C8—H80.9300
O4—C151.4173 (19)C9—C141.383 (2)
O5—C131.3729 (19)C9—C101.404 (2)
O5—C161.4254 (19)C10—C111.383 (2)
O6—H170.8500C11—C121.384 (2)
O6—H180.8508C11—H110.9300
N1—C71.3501 (18)C12—C131.384 (2)
N1—N21.3770 (17)C12—H120.9300
N1—H1A0.8595C13—C141.382 (2)
N2—C81.2740 (19)C14—H140.9300
C1—C61.387 (2)C15—H15A0.9600
C1—C21.396 (2)C15—H15B0.9600
C1—C71.482 (2)C15—H15C0.9600
C2—C31.380 (2)C16—H16A0.9600
C2—H2A0.9300C16—H16B0.9600
C3—C41.399 (2)C16—H16C0.9600
C3—O1—H1109.5C9—C8—H8120.4
C4—O2—H2109.4C14—C9—C10119.21 (14)
C10—O4—C15117.82 (12)C14—C9—C8119.97 (14)
C13—O5—C16117.19 (13)C10—C9—C8120.76 (14)
H17—O6—H18106.2O4—C10—C11124.61 (14)
C7—N1—N2118.09 (12)O4—C10—C9116.64 (13)
C7—N1—H1A120.9C11—C10—C9118.75 (15)
N2—N1—H1A121.0C10—C11—C12121.29 (15)
C8—N2—N1115.64 (13)C10—C11—H11119.4
C6—C1—C2119.12 (13)C12—C11—H11119.4
C6—C1—C7118.53 (13)C11—C12—C13120.12 (14)
C2—C1—C7122.35 (13)C11—C12—H12119.9
C3—C2—C1120.64 (13)C13—C12—H12119.9
C3—C2—H2A119.7O5—C13—C14115.51 (14)
C1—C2—H2A119.7O5—C13—C12125.69 (14)
O1—C3—C2124.19 (13)C14—C13—C12118.78 (15)
O1—C3—C4116.44 (13)C13—C14—C9121.79 (15)
C2—C3—C4119.36 (13)C13—C14—H14119.1
O2—C4—C5119.11 (13)C9—C14—H14119.1
O2—C4—C3120.48 (13)O4—C15—H15A109.5
C5—C4—C3120.41 (13)O4—C15—H15B109.5
C4—C5—C6119.89 (14)H15A—C15—H15B109.5
C4—C5—H5120.1O4—C15—H15C109.5
C6—C5—H5120.1H15A—C15—H15C109.5
C1—C6—C5120.56 (14)H15B—C15—H15C109.5
C1—C6—H6119.7O5—C16—H16A109.5
C5—C6—H6119.7O5—C16—H16B109.5
O3—C7—N1121.84 (13)H16A—C16—H16B109.5
O3—C7—C1122.25 (13)O5—C16—H16C109.5
N1—C7—C1115.91 (12)H16A—C16—H16C109.5
N2—C8—C9119.18 (14)H16B—C16—H16C109.5
N2—C8—H8120.4
C7—N1—N2—C8177.35 (14)N1—N2—C8—C9−176.41 (13)
C6—C1—C2—C3−1.5 (2)N2—C8—C9—C14−0.8 (2)
C7—C1—C2—C3177.70 (13)N2—C8—C9—C10176.25 (15)
C1—C2—C3—O1−179.19 (13)C15—O4—C10—C11−4.8 (2)
C1—C2—C3—C42.0 (2)C15—O4—C10—C9175.43 (14)
O1—C3—C4—O20.1 (2)C14—C9—C10—O4−177.86 (14)
C2—C3—C4—O2179.00 (13)C8—C9—C10—O45.1 (2)
O1—C3—C4—C5179.83 (13)C14—C9—C10—C112.4 (2)
C2—C3—C4—C5−1.2 (2)C8—C9—C10—C11−174.70 (14)
O2—C4—C5—C6179.82 (14)O4—C10—C11—C12179.15 (15)
C3—C4—C5—C60.1 (2)C9—C10—C11—C12−1.1 (2)
C2—C1—C6—C50.3 (2)C10—C11—C12—C13−0.9 (2)
C7—C1—C6—C5−178.94 (14)C16—O5—C13—C14172.04 (16)
C4—C5—C6—C10.4 (2)C16—O5—C13—C12−6.2 (3)
N2—N1—C7—O30.1 (2)C11—C12—C13—O5179.70 (15)
N2—N1—C7—C1179.86 (13)C11—C12—C13—C141.5 (2)
C6—C1—C7—O3−21.2 (2)O5—C13—C14—C9−178.57 (14)
C2—C1—C7—O3159.56 (15)C12—C13—C14—C9−0.2 (2)
C6—C1—C7—N1159.05 (14)C10—C9—C14—C13−1.8 (2)
C2—C1—C7—N1−20.2 (2)C8—C9—C14—C13175.35 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.822.032.8384 (15)168
O2—H2···O10.822.252.7014 (15)115
O2—H2···O5i0.822.433.0191 (15)130
O6—H17···O2ii0.852.062.9003 (15)169
O6—H18···O3i0.851.952.7837 (15)165
N1—H1A···O60.862.162.8592 (17)138
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formulaC16H16N2O5·H2O
Mr334.32
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)10.2573 (8), 12.4199 (10), 14.0042 (8)
β (°) 119.666 (4)
V (Å3)1550.2 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.20 × 0.18 × 0.17
Data collection
DiffractometerSiemens SMART CCD
Absorption correctionMulti-scan
(SADABS; Siemens, 1996)
Tmin, Tmax0.978, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections		7993, 2735, 2110
Rint0.060
(sin θ/λ)max (Å−1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.098, 1.02
No. of reflections2735
No. of parameters220
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.30, −0.15

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.822.032.8384 (15)168
O2—H2···O10.822.252.7014 (15)115
O2—H2···O5i0.822.433.0191 (15)130
O6—H17···O2ii0.852.062.9003 (15)169
O6—H18···O3i0.851.952.7837 (15)165
N1—H1A···O60.862.162.8592 (17)138
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z.
 

Footnotes

‡Additional correspondence author, e-mail: qihui79@hotmail.com.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science Google Scholar
 First citationPu, X.-H. (2008). Acta Cryst. E64, o1734.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSiemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationWang, S.-Y., Yuan, L., Xu, L., Zhang, Z., Diao, Y.-P. & Lv, D.-C. (2009). Acta Cryst. E65, o1154.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page o2615
https://doi.org/10.1107/S1600536809039300
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