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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 64| Part 1| January 2008| Page o82
https://doi.org/10.1107/S1600536807062708

2′-(3-Hy­droxy­benzyl­­idene)pyrazine-2-carbohydrazide monohydrate

Lei Hea*

aDepartment of Chemistry, Tianjin University, Tianjin 300072, People's Republic of China
*Correspondence e-mail: tjuhelei@yahoo.com.cn

(Received 22 November 2007; accepted 23 November 2007; online 6 December 2007)

The title compound, C12H10N4O2·H2O, was synthesized by the reaction of pyrazine-2-carboxylic acid hydrazide and 3-hydroxy­benzaldehyde in ethanol. In the crystal structure, the organic mol­ecules are linked into extended chains by inter­molecular N(amide)—H⋯O(hydr­oxy) hydrogen bonds. Additional hydrogen bonds between the water mol­ecule and three adjacent organic mol­ecules, as well as face-to-face π–π stacking inter­actions between the benzene and pyrazine rings [centroid-to-centroid separation = 3.669 (2) Å and offset = 1.362 Å], link the mol­ecules into a three-dimensional framework.

Related literature

For pharmacological and photochromic properties of hydrazone­carbonyl compounds, see: Parashar et al. (1988[Parashar, R. K., Sharma, R. C., Kumar, A. & Mohan, G. (1988). Inorg. Chim. Acta, 151, 201-208.]); Hadjoudis et al. (1987[Hadjoudis, E., Vittorakis, M. & Moustakali-Mavridis, I. (1987). Tetrahedron, 43, 1345-1360.]). For related pyrazinecarboxylic acid hydrazones, see: Gardner et al. (1956[Gardner, T. S., Smith, F. A., Wenis, E. & Lee, J. (1956). J. Org. Chem. 21, 530-533.]);

[Scheme 1]

Experimental

Crystal data

  • C12H10N4O2·H2O

  • Mr = 260.26

  • Triclinic, [P \overline 1]

  • a = 8.062 (3) Å

  • b = 8.186 (3) Å

  • c = 9.449 (3) Å

  • α = 95.122 (6)°

  • β = 103.169 (6)°

  • γ = 99.827 (7)°

  • V = 592.9 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 294 (2) K

  • 0.24 × 0.22 × 0.18 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.962, Tmax = 0.981

  • 3017 measured reflections

  • 2083 independent reflections

  • 1112 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.140

  • S = 1.02

  • 2083 reflections

  • 184 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2⋯O3i 0.86 (4) 1.78 (4) 2.634 (3) 174 (4)
N3—H3⋯N1 0.82 (3) 2.31 (3) 2.705 (3) 110 (3)
N3—H3⋯O2ii 0.82 (3) 2.51 (3) 3.218 (4) 145 (3)
O3—H3B⋯N2iii 0.86 (2) 2.04 (3) 2.873 (3) 163 (4)
O3—H3C⋯N4 0.89 (2) 2.22 (3) 3.043 (3) 152 (3)
O3—H3C⋯O1 0.89 (2) 2.29 (3) 2.982 (3) 134 (3)
Symmetry codes: (i) -x, -y+2, -z+1; (ii) x, y-1, z; (iii) -x+1, -y+1, -z+2.

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SMART; data reduction: SAINT (Bruker, 1997[Bruker (1997). SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Bruker, 1997[Bruker (1997). SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807062708/ln2011sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062708/ln2011Isup2.hkl

checkCIF report


Comment top

Hydrazonecarbonyl compounds have received considerable attention due to their pharmacological activities (Parashar et al., 1988) and photochromic properties (Hadjoudis et al., 1987). A series of similar pyrazinylcarboxylic acid hydrazones has been reported previously (Gardner et al., 1956). As a continuation of the work of our group, we report here the crystal structure of 2'-(3-hydroxybenzylidene)pyrazine-2-carbohydrazide monohydrate, (I).

The asymmetric unit contains one organic molecule and one molecule of H2O. The carbohydrazide molecule deviates only slightly from planarity with a dihedral angle of 11.60 (3)° between the planes of the pyrazinyl and phenyl rings (Fig. 1).

In the crystal, the organic molecules of (I) are arranged in slightly tilted rows. Within the rows, amide atom N3 acts as a hydrogen bond donor to the atom O2 of the hydroxy group in a neighbouring molecule, thereby forming extended chains, which run parallel to the a axis (Table 1, Fig. 2).

The water O atom acts as a hydrogen bond acceptor from the hydroxy group of an organic molecule. One water H atom forms a hydrogen bond with the N atom in the pyrazinyl ring of another adjacent molecule, while the other H atom forms bifurcated hydrogen bonds with the carbonyl O atom, O1, and the N4 atom from another molecule of I, thereby forming a five-membered hydrogen bond ring (Fig. 3).

The crystal packing is characterized by π···π stacking interactions. The molecules are stacked in an antiparalled fashion, with a pyrazinyl to phenyl ring centroid-centroid separation of 3.669 (2) Å and an offset of 1.362 Å. Together with the hydrogen bonds, these interactions lead to a three-dimensional supramolecular network pattern (Fig. 3).

Related literature top

For pharmacological and photochromic properties of hydrazonecarbonyl compounds, see: Parashar et al. (1988); Hadjoudis et al. (1987). For related pyrazinylcarboxylic acid hydrazones, see: Gardner et al. (1956)

Experimental top

Compound (I) was synthesized by the reaction of pyrazine-2-carboxylic acid hydrazide (0.01 mol, 1.38 g) and 3-hydroxybenzaldehyde (0.01 mol, 1.52 g) in ethanol. The solution was refluxed for 3 h. After cooling down, the solid product was filtered and recrystallized from ethanol with a yield of 75%, m.p. 540–541 K. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of a mixture of methanol and water (5: 1).

Refinement top

All H atoms were initially located in a difference Fourier map. The carbon bound H atoms were then constrained to an ideal geometry, with C(phenyl)—H distances of 0.93 Å and Uiso(H) = 1.2Ueq(C). The H atoms attached to the hydroxy and water O atoms and to the N atom were refined freely with Uiso(H) = 1.5Ueq(O) and 1.2Ueq(N), respectively.

Structure description top

Hydrazonecarbonyl compounds have received considerable attention due to their pharmacological activities (Parashar et al., 1988) and photochromic properties (Hadjoudis et al., 1987). A series of similar pyrazinylcarboxylic acid hydrazones has been reported previously (Gardner et al., 1956). As a continuation of the work of our group, we report here the crystal structure of 2'-(3-hydroxybenzylidene)pyrazine-2-carbohydrazide monohydrate, (I).

The asymmetric unit contains one organic molecule and one molecule of H2O. The carbohydrazide molecule deviates only slightly from planarity with a dihedral angle of 11.60 (3)° between the planes of the pyrazinyl and phenyl rings (Fig. 1).

In the crystal, the organic molecules of (I) are arranged in slightly tilted rows. Within the rows, amide atom N3 acts as a hydrogen bond donor to the atom O2 of the hydroxy group in a neighbouring molecule, thereby forming extended chains, which run parallel to the a axis (Table 1, Fig. 2).

The water O atom acts as a hydrogen bond acceptor from the hydroxy group of an organic molecule. One water H atom forms a hydrogen bond with the N atom in the pyrazinyl ring of another adjacent molecule, while the other H atom forms bifurcated hydrogen bonds with the carbonyl O atom, O1, and the N4 atom from another molecule of I, thereby forming a five-membered hydrogen bond ring (Fig. 3).

The crystal packing is characterized by π···π stacking interactions. The molecules are stacked in an antiparalled fashion, with a pyrazinyl to phenyl ring centroid-centroid separation of 3.669 (2) Å and an offset of 1.362 Å. Together with the hydrogen bonds, these interactions lead to a three-dimensional supramolecular network pattern (Fig. 3).

For pharmacological and photochromic properties of hydrazonecarbonyl compounds, see: Parashar et al. (1988); Hadjoudis et al. (1987). For related pyrazinylcarboxylic acid hydrazones, see: Gardner et al. (1956)

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top
[Figure 1] Fig. 1. The structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. View along the c axis showing a one-dimensional chain of the organic molecule. The water molecules have been omitted for clarity. Dashed lines represent the hydrogen bonds. Symmetry code: (A) x, y - 1, z.
[Figure 3] Fig. 3. The crystal packing viewed down the a axis showing the three-dimensional structure formed by hydrogen bonds (dashed lines) and π···π stacking interactions.
2'-(3-Hydroxybenzylidene)pyrazine-2-carbohydrazide monohydrate top
Crystal data top
C12H10N4O2·H2OZ = 2
Mr = 260.26F(000) = 272
Triclinic, P1Dx = 1.458 Mg m−3
a = 8.062 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.186 (3) ÅCell parameters from 658 reflections
c = 9.449 (3) Åθ = 2.2–23.0°
α = 95.122 (6)°µ = 0.11 mm−1
β = 103.169 (6)°T = 294 K
γ = 99.827 (7)°Block, colourless
V = 592.9 (4) Å30.24 × 0.22 × 0.18 mm
Data collection top
Bruker CCD area-detector
diffractometer		2083 independent reflections
Radiation source: fine-focus sealed tube1112 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→9
Tmin = 0.962, Tmax = 0.981k = −9→4
3017 measured reflectionsl = −10→11
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0631P)2]
where P = (Fo2 + 2Fc2)/3
2083 reflections(Δ/σ)max < 0.001
184 parametersΔρmax = 0.20 e Å−3
0 restraintsΔρmin = −0.23 e Å−3
Crystal data top
C12H10N4O2·H2Oγ = 99.827 (7)°
Mr = 260.26V = 592.9 (4) Å3
Triclinic, P1Z = 2
a = 8.062 (3) ÅMo Kα radiation
b = 8.186 (3) ŵ = 0.11 mm−1
c = 9.449 (3) ÅT = 294 K
α = 95.122 (6)°0.24 × 0.22 × 0.18 mm
β = 103.169 (6)°
Data collection top
Bruker CCD area-detector
diffractometer		2083 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1112 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.981Rint = 0.024
3017 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.140H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.20 e Å−3
2083 reflectionsΔρmin = −0.23 e Å−3
184 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
O10.4727 (3)0.5725 (3)0.7739 (2)0.0587 (7)
O20.0678 (3)1.0884 (3)0.3575 (3)0.0567 (7)
H2−0.014 (5)1.134 (5)0.314 (4)0.085*
N10.4525 (3)0.1480 (3)0.6449 (2)0.0392 (7)
N20.6326 (3)0.1543 (3)0.9355 (3)0.0472 (7)
N30.3179 (4)0.4148 (3)0.5600 (3)0.0397 (7)
H30.299 (4)0.322 (4)0.513 (3)0.048*
N40.2524 (3)0.5480 (3)0.5068 (3)0.0402 (7)
C10.5113 (4)0.0166 (4)0.6931 (3)0.0448 (9)
H10.4921−0.08080.62810.054*
C20.6005 (4)0.0195 (4)0.8370 (3)0.0465 (9)
H2A0.6393−0.07600.86580.056*
C30.5740 (4)0.2865 (4)0.8871 (3)0.0444 (8)
H3A0.59300.38360.95250.053*
C40.4858 (4)0.2849 (4)0.7429 (3)0.0337 (7)
C50.4252 (4)0.4375 (4)0.6954 (3)0.0398 (8)
C60.1605 (4)0.5199 (4)0.3753 (3)0.0388 (8)
H60.14400.41390.32350.047*
C70.0801 (4)0.6459 (4)0.3024 (3)0.0355 (8)
C8−0.0298 (4)0.5994 (4)0.1629 (3)0.0434 (9)
H8−0.05120.48920.11880.052*
C9−0.1069 (4)0.7147 (4)0.0899 (3)0.0501 (9)
H9−0.18030.6823−0.00340.060*
C10−0.0764 (4)0.8785 (4)0.1537 (3)0.0450 (9)
H10−0.12860.95650.10350.054*
C110.0317 (4)0.9261 (4)0.2922 (3)0.0378 (8)
C120.1093 (4)0.8114 (4)0.3664 (3)0.0385 (8)
H120.18180.84440.46000.046*
O30.1948 (3)0.7733 (3)0.7579 (2)0.0590 (7)
H3B0.242 (5)0.816 (4)0.847 (3)0.088*
H3C0.246 (5)0.708 (4)0.708 (4)0.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0769 (18)0.0433 (15)0.0455 (14)0.0237 (13)−0.0117 (13)−0.0016 (12)
O20.0651 (17)0.0367 (14)0.0564 (15)0.0197 (12)−0.0147 (12)0.0016 (11)
N10.0441 (16)0.0446 (17)0.0289 (14)0.0186 (14)0.0008 (12)0.0061 (13)
N20.0529 (18)0.0528 (19)0.0355 (16)0.0205 (15)−0.0003 (13)0.0138 (14)
N30.0492 (17)0.0342 (16)0.0355 (16)0.0202 (15)0.0004 (13)0.0076 (12)
N40.0455 (16)0.0401 (16)0.0378 (16)0.0203 (14)0.0037 (13)0.0139 (13)
C10.055 (2)0.044 (2)0.0365 (19)0.0190 (18)0.0060 (16)0.0072 (16)
C20.055 (2)0.048 (2)0.040 (2)0.0218 (19)0.0064 (17)0.0158 (17)
C30.051 (2)0.045 (2)0.0348 (19)0.0150 (17)0.0024 (16)0.0059 (16)
C40.0332 (17)0.0430 (19)0.0275 (17)0.0159 (15)0.0051 (14)0.0083 (15)
C50.0407 (19)0.046 (2)0.0343 (19)0.0171 (17)0.0045 (16)0.0085 (17)
C60.047 (2)0.0365 (19)0.0335 (19)0.0132 (16)0.0068 (16)0.0080 (14)
C70.0358 (18)0.0397 (19)0.0338 (18)0.0164 (16)0.0049 (15)0.0120 (15)
C80.056 (2)0.0376 (19)0.0332 (19)0.0139 (17)0.0012 (16)0.0039 (15)
C90.063 (2)0.051 (2)0.0303 (18)0.0224 (19)−0.0075 (16)0.0037 (16)
C100.051 (2)0.047 (2)0.0360 (19)0.0238 (18)−0.0039 (16)0.0116 (16)
C110.0393 (19)0.0331 (19)0.0390 (19)0.0111 (16)0.0025 (15)0.0059 (15)
C120.0388 (19)0.042 (2)0.0324 (18)0.0129 (16)−0.0016 (15)0.0079 (15)
O30.0716 (18)0.0561 (17)0.0466 (15)0.0334 (14)−0.0036 (13)0.0000 (13)
Geometric parameters (Å, º) top
O1—C51.224 (4)C4—C51.486 (4)
O2—C111.368 (4)C6—C71.453 (4)
O2—H20.86 (4)C6—H60.9300
N1—C11.324 (4)C7—C81.390 (4)
N1—C41.336 (3)C7—C121.391 (4)
N2—C21.327 (4)C8—C91.369 (4)
N2—C31.330 (4)C8—H80.9300
N3—C51.348 (4)C9—C101.377 (4)
N3—N41.376 (3)C9—H90.9300
N3—H30.82 (3)C10—C111.377 (4)
N4—C61.272 (3)C10—H100.9300
C1—C21.382 (4)C11—C121.373 (4)
C1—H10.9300C12—H120.9300
C2—H2A0.9300O3—H3B0.86 (2)
C3—C41.384 (4)O3—H3C0.89 (2)
C3—H3A0.9300
C11—O2—H2106 (3)N4—C6—C7122.9 (3)
C1—N1—C4116.3 (3)N4—C6—H6118.5
C2—N2—C3115.9 (3)C7—C6—H6118.5
C5—N3—N4119.2 (3)C8—C7—C12118.7 (3)
C5—N3—H3117 (2)C8—C7—C6118.7 (3)
N4—N3—H3124 (2)C12—C7—C6122.6 (3)
C6—N4—N3115.7 (3)C9—C8—C7120.5 (3)
N1—C1—C2122.1 (3)C9—C8—H8119.8
N1—C1—H1118.9C7—C8—H8119.8
C2—C1—H1118.9C8—C9—C10120.4 (3)
N2—C2—C1122.1 (3)C8—C9—H9119.8
N2—C2—H2A119.0C10—C9—H9119.8
C1—C2—H2A119.0C9—C10—C11119.7 (3)
N2—C3—C4122.4 (3)C9—C10—H10120.1
N2—C3—H3A118.8C11—C10—H10120.1
C4—C3—H3A118.8O2—C11—C12118.5 (3)
N1—C4—C3121.3 (3)O2—C11—C10121.2 (3)
N1—C4—C5119.0 (3)C12—C11—C10120.3 (3)
C3—C4—C5119.7 (3)C11—C12—C7120.4 (3)
O1—C5—N3123.6 (3)C11—C12—H12119.8
O1—C5—C4121.7 (3)C7—C12—H12119.8
N3—C5—C4114.7 (3)H3B—O3—H3C122 (4)
C5—N3—N4—C6176.0 (3)C3—C4—C5—N3−170.0 (3)
C4—N1—C1—C20.8 (4)N3—N4—C6—C7179.4 (3)
C3—N2—C2—C1−0.2 (5)N4—C6—C7—C8−174.7 (3)
N1—C1—C2—N20.0 (5)N4—C6—C7—C125.6 (5)
C2—N2—C3—C4−0.3 (5)C12—C7—C8—C90.3 (4)
C1—N1—C4—C3−1.3 (4)C6—C7—C8—C9−179.4 (3)
C1—N1—C4—C5179.2 (3)C7—C8—C9—C100.0 (5)
N2—C3—C4—N11.1 (5)C8—C9—C10—C11−0.3 (5)
N2—C3—C4—C5−179.4 (3)C9—C10—C11—O2178.6 (3)
N4—N3—C5—O1−2.0 (5)C9—C10—C11—C120.2 (5)
N4—N3—C5—C4179.0 (3)O2—C11—C12—C7−178.2 (3)
N1—C4—C5—O1−169.5 (3)C10—C11—C12—C70.2 (5)
C3—C4—C5—O111.0 (5)C8—C7—C12—C11−0.5 (4)
N1—C4—C5—N39.5 (4)C6—C7—C12—C11179.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.86 (4)1.78 (4)2.634 (3)174 (4)
N3—H3···N10.82 (3)2.31 (3)2.705 (3)110 (3)
N3—H3···O2ii0.82 (3)2.51 (3)3.218 (4)145 (3)
O3—H3B···N2iii0.86 (2)2.04 (3)2.873 (3)163 (4)
O3—H3C···N40.89 (2)2.22 (3)3.043 (3)152 (3)
O3—H3C···O10.89 (2)2.29 (3)2.982 (3)134 (3)
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x, y−1, z; (iii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formulaC12H10N4O2·H2O
Mr260.26
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)8.062 (3), 8.186 (3), 9.449 (3)
α, β, γ (°)95.122 (6), 103.169 (6), 99.827 (7)
V (Å3)592.9 (4)
Z2
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.24 × 0.22 × 0.18
Data collection
DiffractometerBruker CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.962, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections		3017, 2083, 1112
Rint0.024
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.140, 1.02
No. of reflections2083
No. of parameters184
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.20, −0.23

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.86 (4)1.78 (4)2.634 (3)174 (4)
N3—H3···N10.82 (3)2.31 (3)2.705 (3)110 (3)
N3—H3···O2ii0.82 (3)2.51 (3)3.218 (4)145 (3)
O3—H3B···N2iii0.86 (2)2.04 (3)2.873 (3)163 (4)
O3—H3C···N40.89 (2)2.22 (3)3.043 (3)152 (3)
O3—H3C···O10.89 (2)2.29 (3)2.982 (3)134 (3)
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x, y−1, z; (iii) −x+1, −y+1, −z+2.
 

References

First citationBruker (1997). SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationGardner, T. S., Smith, F. A., Wenis, E. & Lee, J. (1956). J. Org. Chem. 21, 530–533.  CrossRef CAS Web of Science Google Scholar
 First citationHadjoudis, E., Vittorakis, M. & Moustakali-Mavridis, I. (1987). Tetrahedron, 43, 1345–1360.  CrossRef CAS Web of Science Google Scholar
 First citationParashar, R. K., Sharma, R. C., Kumar, A. & Mohan, G. (1988). Inorg. Chim. Acta, 151, 201–208.  CrossRef CAS Web of Science Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar

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ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o82
https://doi.org/10.1107/S1600536807062708
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