N′-[(E)-(3-Fluoro­pyridin-2-yl)methyl­idene]benzohydrazide monohydrate

Nair, Y.; Sithambaresan, M.; Kurup, M.R.P.

doi:10.1107/S1600536812035179

organic compounds

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Volume 68| Part 9| September 2012| Page o2709

doi:10.1107/S1600536812035179

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N′-[(E)-(3-Fluoropyridin-2-yl)methylidene]benzohydrazide monohydrate

Yamuna Nair,^a M. Sithambaresan ^b ^* and M. R. Prathapachandra Kurup ^c

^aDepartment of Chemical Oceanography, Cochin University of Science and Technology, Lakeside Campus, Kochi 682 016, India, ^bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka, and ^cDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India
^*Correspondence e-mail: eesans@yahoo.com

(Received 10 July 2012; accepted 8 August 2012; online 15 August 2012)

The title compound, C₁₃H₁₀FN₃O·H₂O, exists in the E conformation with respect to the azomethane C=N double bond. The molecule is close to planar with a maximum deviation of 0.286 (2) Å. The pyridine ring is essentially coplanar with the central C(= O)N₂C unit [dihedral angle = 2.02 (3)°] and the phenyl ring exhibits a dihedral angle of 14.41 (10)° with respect to the central unit. The crystal structure features O—H⋯N, N—H⋯O and O—H⋯O hydrogen-bond interactions between the solvent water and the benzohydrazide molecules, as well as C—H⋯O hydrogen bonds and C—F⋯π [3.0833 (18) Å] interactions.

Related literature

For background to the use of benzohydrazides as catalysts, see: Heravi et al. (2007 ); Hou et al. (2005 ) and for their biological activity, see: Sreeja et al. (2004 ). For the synthesis of related compounds, see: Fun et al. (2008 ). For related structures, see Mangalam et al. (2009 ).

Experimental

Crystal data

C₁₃H₁₀FN₃O·H₂O
M_r = 261.26
Orthorhombic, P b c a
a = 8.2540 (4) Å
b = 11.5489 (4) Å
c = 26.1962 (11) Å
V = 2497.14 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.964, T_max = 0.974
34264 measured reflections
2192 independent reflections
1817 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.096
S = 1.07
2190 reflections
185 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3′⋯O1W	0.901 (18)	1.914 (18)	2.7917 (17)	164.3 (16)
O1W—H1A⋯O1ⁱ	0.84 (3)	2.08 (3)	2.9187 (19)	172 (2)
O1W—H1A⋯N2ⁱ	0.84 (3)	2.48 (2)	2.9494 (17)	116.1 (19)
O1W—H1B⋯N1ⁱ	0.89 (2)	1.95 (3)	2.8420 (18)	178 (2)
C9—H9⋯O1W	0.93	2.30	3.209 (2)	165
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2010 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812035179/zl2494sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812035179/zl2494Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812035179/zl2494Isup3.cml

checkCIF report

Comment top

Interest in coordination chemistry of benzohydrazide has been a subject of enthusiastic research since their complexes show a wide range of catalytic properties (Heravi et al., 2007; Hou et al., 2005). Benzohydrazone derivatives are also important due to their wide spectrum of biological activities (Sreeja et al., 2004).

This molecule adopts an E conformation with respect to the C6=N2 bond and it exists in the amido form with a C7=O1 bond length of 1.2258 (17) Å which is very close to the reported C=O bond length of a similar structure (Mangalam et al., 2009). The O1 and N2 atoms are in a Z conformation with respect to C7–N3 having a torsional angle of -0.4 (2)°. The molecule is almost planar with a maximum deviation of 0.286 (2) Å for the atom C12 from its least square plane. The pyridyl ring is essentially coplanar with the central C(=O)N₂C unit (dihedral angle 2.02 (3) °), the phenyl ring exhibits a dihedral angle of 14.41 (10)° with respect to the central unit.

The water molecule forms six H-bonds with two different benzohydrazone molecules. Hydrogen bond interactions such as O–H···N, O–H···O, N–H···O and C–H···O are present in the crystal system between the H atoms attached to the O1W atom and N1, N2, N3, C9 and O1 atoms of two adjacent molecules with D···A distances of 2.842 (2), 2.9495 (17), 2.7917 (17), 3.209 (2) and 2.9188 (18) Å respectively as shown in Table 1. Both H-atoms of the water molecule form bifurcated hydrogen bonds with the azomethine nitrogen, the pyridyl nitrogen and the carbonyl oxygen atoms of one neighboring molecule (Fig. 2). The water molecule acts as a hydrogen bond acceptor towards another benzohydrazone molecule through an N–H···O hydrogen bond. Through these interactions the molecules are interconnected through the water molecule to form infinite chains parallel to the b axis of the unit cell (Fig. 2). Benzohydrazone molecules within these chains also interact through weak C–F···π [3.0833 (18) Å] interactions (Fig. 2) that augment the stronger O–H···N, O–H···O, N–H···O hydrogen bonds.

Related literature top

For catalytic properties of benzohydrazides, see: Heravi et al. (2007); Hou et al. (2005) and for their biological activity, see: Sreeja et al. (2004). For the synthesis of related compounds, see: Fun et al. (2008). For related structures, see Mangalam et al. (2009).

Experimental top

The title compound was prepared by adapting a reported procedure (Fun et al., 2008). A solution of 3-fluoropyridine-2-carbaldehyde (1.25 g,1 mmol) in ethanol (10 ml) was mixed with an ethanolic solution (10 ml) of benzohydrazide (1.36 g,1 mmol). The mixture was boiled under reflux for 12 h after adding few drops of glacial acetic acid and then cooled to room temperature. Colorless block shaped crystals, suitable for single-crystal analysis, were obtained in 61.8% yield after slow evaporation of the solution in air for a few days. ¹H NMR spectrum, DMSO-d₆, δ, p.p.m.: 12.12 (s, 1H, NH), 8.66 (s, 1H, CH=N), 8.53 (d, 1H, py–H(C1)), 7.54–7.95 (m, 7H, Ar–H (C2, C3, C9, C10, C11, C12, C13)). IR spectrum, ν (cm^-1): 3421, 3059, 1683,1650, 1597, 1441, 1350, 1295, 1273, 1167, 1134, 1073, 922, 801, 706, 674.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

Fig. 1. ORTEP diagram of N'-[(E)-(3-fluoropyridin-2-yl)methylidene]benzohydrazide monohydrate with 50% probability ellipsoids.

Fig. 2. Hydrogen-bonding interactions showing an infinite chain in the crystal structure of N'-[(E)-(3-fluoropyridin-2-yl)methylidene]benzohydrazide hydrate and the interconnection of the chains via weak C–F···π interactions.

N'-[(E)-(3-Fluoropyridin-2-yl)methylidene]benzohydrazide monohydrate top

Crystal data top

C₁₃H₁₀FN₃O·H₂O	F(000) = 1088
M_r = 261.26	D_x = 1.390 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9884 reflections
a = 8.2540 (4) Å	θ = 5.8–54.5°
b = 11.5489 (4) Å	µ = 0.11 mm⁻¹
c = 26.1962 (11) Å	T = 296 K
V = 2497.14 (18) Å³	Block, colorless
Z = 8	0.35 × 0.30 × 0.25 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2192 independent reflections
Radiation source: fine-focus sealed tube	1817 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scan	θ_max = 25.0°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
T_min = 0.964, T_max = 0.974	k = −13→13
34264 measured reflections	l = −31→31

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0425P)² + 0.6736P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
2190 reflections	Δρ_max = 0.18 e Å⁻³
185 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0073 (8)

Crystal data top

C₁₃H₁₀FN₃O·H₂O	V = 2497.14 (18) Å³
M_r = 261.26	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.2540 (4) Å	µ = 0.11 mm⁻¹
b = 11.5489 (4) Å	T = 296 K
c = 26.1962 (11) Å	0.35 × 0.30 × 0.25 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2192 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1817 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.974	R_int = 0.027
34264 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.18 e Å⁻³
2190 reflections	Δρ_min = −0.13 e Å⁻³
185 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
F1	0.75071 (13)	0.87133 (8)	1.09485 (3)	0.0629 (3)
O1	0.82638 (15)	1.12491 (9)	0.86590 (4)	0.0561 (3)
O1W	0.90084 (17)	0.73757 (10)	0.93534 (6)	0.0600 (3)
N1	0.60294 (15)	1.12483 (10)	1.03176 (5)	0.0462 (3)
N2	0.79363 (14)	1.02906 (10)	0.95707 (4)	0.0413 (3)
N3	0.88214 (15)	0.97616 (11)	0.91928 (4)	0.0418 (3)
C1	0.51707 (19)	1.17020 (13)	1.06961 (6)	0.0514 (4)
H1	0.4633	1.2397	1.0637	0.062*
C2	0.5032 (2)	1.12006 (14)	1.11710 (6)	0.0562 (4)
H2	0.4420	1.1552	1.1425	0.067*
C3	0.5812 (2)	1.01773 (15)	1.12616 (6)	0.0557 (4)
H3	0.5742	0.9811	1.1577	0.067*
C4	0.66988 (18)	0.97122 (13)	1.08709 (5)	0.0444 (4)
C5	0.68155 (16)	1.02434 (11)	1.04024 (5)	0.0392 (3)
C6	0.77636 (17)	0.97353 (12)	0.99866 (5)	0.0416 (3)
H6	0.8237	0.9010	1.0026	0.050*
C7	0.89290 (17)	1.03168 (12)	0.87370 (5)	0.0416 (3)
C8	0.99453 (17)	0.97527 (13)	0.83362 (5)	0.0427 (3)
C9	1.0457 (2)	0.86099 (14)	0.83555 (6)	0.0543 (4)
H9	1.0176	0.8148	0.8633	0.065*
C10	1.1385 (2)	0.81533 (17)	0.79643 (6)	0.0664 (5)
H10	1.1715	0.7384	0.7978	0.080*
C11	1.1819 (2)	0.88324 (18)	0.75569 (7)	0.0692 (5)
H11	1.2441	0.8522	0.7294	0.083*
C12	1.1337 (2)	0.99666 (18)	0.75360 (6)	0.0650 (5)
H12	1.1645	1.0427	0.7261	0.078*
C13	1.03959 (19)	1.04278 (15)	0.79213 (6)	0.0529 (4)
H13	1.0062	1.1196	0.7903	0.064*
H3'	0.908 (2)	0.9010 (16)	0.9235 (6)	0.057 (5)*
H1A	0.838 (3)	0.699 (2)	0.9166 (9)	0.102 (9)*
H1B	0.902 (3)	0.701 (2)	0.9653 (9)	0.100 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0738 (6)	0.0639 (6)	0.0511 (5)	0.0185 (5)	0.0040 (5)	0.0128 (4)
O1	0.0757 (8)	0.0461 (6)	0.0467 (6)	0.0037 (5)	0.0021 (5)	0.0061 (5)
O1W	0.0761 (8)	0.0452 (6)	0.0589 (8)	−0.0080 (6)	0.0070 (7)	0.0081 (6)
N1	0.0496 (7)	0.0422 (7)	0.0468 (7)	0.0015 (5)	0.0020 (6)	−0.0028 (5)
N2	0.0454 (7)	0.0418 (6)	0.0366 (6)	−0.0004 (5)	0.0024 (5)	−0.0031 (5)
N3	0.0500 (7)	0.0406 (7)	0.0348 (6)	0.0017 (5)	0.0046 (5)	−0.0004 (5)
C1	0.0508 (9)	0.0451 (8)	0.0583 (10)	0.0016 (7)	0.0051 (7)	−0.0096 (7)
C2	0.0529 (9)	0.0628 (10)	0.0528 (10)	−0.0014 (8)	0.0107 (7)	−0.0155 (8)
C3	0.0571 (9)	0.0704 (11)	0.0395 (8)	−0.0017 (8)	0.0053 (7)	−0.0008 (7)
C4	0.0447 (8)	0.0492 (8)	0.0395 (8)	0.0006 (7)	−0.0027 (6)	−0.0008 (6)
C5	0.0381 (7)	0.0417 (7)	0.0377 (7)	−0.0032 (6)	−0.0013 (6)	−0.0039 (6)
C6	0.0459 (8)	0.0401 (8)	0.0388 (7)	0.0034 (6)	−0.0001 (6)	−0.0008 (6)
C7	0.0458 (8)	0.0415 (8)	0.0375 (8)	−0.0089 (6)	−0.0036 (6)	−0.0003 (6)
C8	0.0421 (8)	0.0527 (8)	0.0333 (7)	−0.0109 (6)	−0.0020 (6)	−0.0007 (6)
C9	0.0643 (10)	0.0551 (9)	0.0433 (8)	−0.0037 (8)	0.0112 (8)	−0.0003 (7)
C10	0.0736 (12)	0.0708 (11)	0.0550 (10)	0.0039 (9)	0.0161 (9)	−0.0077 (9)
C11	0.0611 (11)	0.1001 (15)	0.0463 (10)	−0.0034 (10)	0.0143 (8)	−0.0098 (10)
C12	0.0576 (10)	0.0987 (14)	0.0386 (9)	−0.0147 (10)	0.0058 (7)	0.0105 (9)
C13	0.0519 (9)	0.0651 (10)	0.0418 (8)	−0.0110 (8)	−0.0024 (7)	0.0068 (7)

Geometric parameters (Å, º) top

F1—C4	1.3481 (17)	C4—C5	1.376 (2)
O1—C7	1.2258 (17)	C5—C6	1.4639 (19)
O1W—H1A	0.84 (3)	C6—H6	0.9300
O1W—H1B	0.89 (2)	C7—C8	1.494 (2)
N1—C1	1.3266 (19)	C8—C9	1.387 (2)
N1—C5	1.3480 (18)	C8—C13	1.388 (2)
N2—C6	1.2721 (18)	C9—C10	1.384 (2)
N2—N3	1.3736 (16)	C9—H9	0.9300
N3—C7	1.3582 (18)	C10—C11	1.372 (3)
N3—H3'	0.901 (18)	C10—H10	0.9300
C1—C2	1.377 (2)	C11—C12	1.370 (3)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.366 (2)	C12—C13	1.381 (2)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.368 (2)	C13—H13	0.9300
C3—H3	0.9300

H1A—O1W—H1B	105 (2)	C5—C6—H6	120.2
C1—N1—C5	118.31 (13)	O1—C7—N3	122.14 (13)
C6—N2—N3	116.90 (12)	O1—C7—C8	121.16 (13)
C7—N3—N2	117.28 (12)	N3—C7—C8	116.67 (13)
C7—N3—H3'	123.2 (11)	C9—C8—C13	118.79 (14)
N2—N3—H3'	117.8 (11)	C9—C8—C7	124.09 (13)
N1—C1—C2	123.60 (15)	C13—C8—C7	117.12 (14)
N1—C1—H1	118.2	C10—C9—C8	120.27 (15)
C2—C1—H1	118.2	C10—C9—H9	119.9
C3—C2—C1	118.79 (14)	C8—C9—H9	119.9
C3—C2—H2	120.6	C11—C10—C9	120.18 (18)
C1—C2—H2	120.6	C11—C10—H10	119.9
C2—C3—C4	117.49 (15)	C9—C10—H10	119.9
C2—C3—H3	121.3	C12—C11—C10	120.13 (17)
C4—C3—H3	121.3	C12—C11—H11	119.9
F1—C4—C3	119.21 (13)	C10—C11—H11	119.9
F1—C4—C5	118.78 (13)	C11—C12—C13	120.19 (16)
C3—C4—C5	122.00 (14)	C11—C12—H12	119.9
N1—C5—C4	119.81 (13)	C13—C12—H12	119.9
N1—C5—C6	118.68 (12)	C12—C13—C8	120.43 (16)
C4—C5—C6	121.51 (13)	C12—C13—H13	119.8
N2—C6—C5	119.67 (12)	C8—C13—H13	119.8
N2—C6—H6	120.2

C6—N2—N3—C7	176.10 (12)	N2—N3—C7—O1	−0.4 (2)
C5—N1—C1—C2	−0.2 (2)	N2—N3—C7—C8	177.81 (11)
N1—C1—C2—C3	−0.2 (2)	O1—C7—C8—C9	−166.31 (14)
C1—C2—C3—C4	0.3 (2)	N3—C7—C8—C9	15.5 (2)
C2—C3—C4—F1	178.90 (14)	O1—C7—C8—C13	13.8 (2)
C2—C3—C4—C5	0.1 (2)	N3—C7—C8—C13	−164.45 (13)
C1—N1—C5—C4	0.6 (2)	C13—C8—C9—C10	−0.7 (2)
C1—N1—C5—C6	179.89 (13)	C7—C8—C9—C10	179.37 (15)
F1—C4—C5—N1	−179.40 (12)	C8—C9—C10—C11	0.7 (3)
C3—C4—C5—N1	−0.5 (2)	C9—C10—C11—C12	0.1 (3)
F1—C4—C5—C6	1.4 (2)	C10—C11—C12—C13	−0.8 (3)
C3—C4—C5—C6	−179.78 (14)	C11—C12—C13—C8	0.8 (3)
N3—N2—C6—C5	−179.18 (11)	C9—C8—C13—C12	0.0 (2)
N1—C5—C6—N2	5.7 (2)	C7—C8—C13—C12	179.90 (14)
C4—C5—C6—N2	−175.10 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3′···O1W	0.901 (18)	1.914 (18)	2.7917 (17)	164.3 (16)
O1W—H1A···O1ⁱ	0.84 (3)	2.08 (3)	2.9187 (19)	172 (2)
O1W—H1A···N2ⁱ	0.84 (3)	2.48 (2)	2.9494 (17)	116.1 (19)
O1W—H1B···N1ⁱ	0.89 (2)	1.95 (3)	2.8420 (18)	178 (2)
C9—H9···O1W	0.93	2.30	3.209 (2)	165

Symmetry code: (i) −x+3/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀FN₃O·H₂O
M_r	261.26
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	8.2540 (4), 11.5489 (4), 26.1962 (11)
V (Å³)	2497.14 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.964, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	34264, 2192, 1817
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.096, 1.07
No. of reflections	2190
No. of parameters	185
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.13

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2010), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3'···O1W	0.901 (18)	1.914 (18)	2.7917 (17)	164.3 (16)
O1W—H1A···O1ⁱ	0.84 (3)	2.08 (3)	2.9187 (19)	172 (2)
O1W—H1A···N2ⁱ	0.84 (3)	2.48 (2)	2.9494 (17)	116.1 (19)
O1W—H1B···N1ⁱ	0.89 (2)	1.95 (3)	2.8420 (18)	178 (2)
C9—H9···O1W	0.9310	2.2991	3.209 (2)	165.38

Symmetry code: (i) −x+3/2, y−1/2, z.

Acknowledgements

The authors are thankful to Dr Shibu M. Eapen, SAIF, Cochin University of Science and Technology, for the data collection.

References

Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Fun, H.-K., Patil, P. S., Rao, J. N., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1707. Web of Science CSD CrossRef IUCr Journals Google Scholar
Heravi, M. M., Ranjbar, L., Derikvand, F., Oskooie, H. A. & Bamoharram, F. F. (2007). J. Mol. Catal. A Chem. 265, 186–188. Web of Science CrossRef CAS Google Scholar
Hou, J., Sun, W.-H., Zhang, D., Chen, L., Li, W., Zhao, D. & Song, H. (2005). J. Mol. Catal. A Chem. 231, 221–233. Web of Science CSD CrossRef CAS Google Scholar
Mangalam, N. A., Sivakumar, S., Sheeja, S. R., Kurup, M. R. P. & Tiekink, E. R. T. (2009). Inorg. Chim. Acta, 362, 4191–4197. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sreeja, P. B., Kurup, M. R. P., Kishore, A. & Jasmin, C. (2004). Polyhedron, 23, 575–581. Web of Science CSD CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar