N′-(3-Phenyl­allyl­idene)nicotinohydrazide monohydrate

R Archana; N Saradhadevi; A Manimekalai; A Thiruvalluvar; R J Butcher

doi:10.1107/S1600536809043001

. 2009 Oct 23;65(Pt 11):o2833. doi: 10.1107/S1600536809043001

N′-(3-Phenylallylidene)nicotinohydrazide monohydrate

R Archana ^a, N Saradhadevi ^b, A Manimekalai ^b, A Thiruvalluvar ^a,^*, R J Butcher ^c

PMCID: PMC2970972 PMID: 21578423

Abstract

In the title compound, C₁₅H₁₃N₃O·H₂O, the dihedral angle between the pyridine and phenyl rings is 35.45 (7)°. Intermolecular O—H⋯O, O—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds are found in the crystal structure. In addition, C—H⋯π interactions involving the pyridine and phenyl rings are also found.

Related literature

For a related crystal structure and its chemical and biological applications, see: Archana et al. (2009 ▶).

Experimental

Crystal data

C₁₅H₁₃N₃O·H₂O
M _r = 269.30
Monoclinic,
a = 9.8456 (3) Å
b = 9.1288 (3) Å
c = 15.5389 (5) Å
β = 95.938 (3)°
V = 1389.12 (8) Å³
Z = 4
Cu Kα radiation
μ = 0.72 mm⁻¹
T = 110 K
0.48 × 0.45 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur, Ruby, Gemini diffractometer
Absorption correction: multi-scan (CrysAlisPro; Oxford Diffraction, 2009 ▶) T _min = 0.704, T _max = 1.000
6007 measured reflections
2742 independent reflections
2346 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.125
S = 1.05
2742 reflections
193 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrysAlisPro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043001/wn2355sup1.cif

e-65-o2833-sup1.cif^{(21.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043001/wn2355Isup2.hkl

e-65-o2833-Isup2.hkl^{(131.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O7ⁱ	0.86 (3)	2.52 (3)	3.1550 (14)	131.9 (19)
O1W—H1W⋯N9ⁱ	0.86 (3)	2.16 (3)	2.9655 (15)	157 (2)
O1W—H2W⋯N1ⁱⁱ	0.88 (3)	2.05 (3)	2.9222 (15)	176 (2)
N8—H8⋯O1W	0.914 (18)	1.944 (18)	2.8486 (15)	170.3 (17)
C2—H2⋯O7ⁱⁱⁱ	0.95	2.33	3.2253 (17)	157
C4—H4⋯O1W	0.95	2.54	3.2392 (16)	130
C10—H10⋯O7ⁱ	0.95	2.57	3.1507 (17)	120
C22—H22⋯Cg1^iv	0.95	2.94	3.7742 (16)	148
C5—H5⋯Cg2^v	0.95	2.54	3.4342 (15)	157

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) . Cg1 and Cg2 are the centroids of the N1–C6 and C21–C26 rings, respectively.

Acknowledgments

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

supplementary crystallographic information

Comment

As part of our research, we have synthesized the title compound and report its crystal structure here. Archana et al. (2009) have reported a related crystal structure, N'-(2-methyl-3-phenylallylidene) nicotinohydrazide monohydrate.

The molecular structure of the asymmetric unit is shown in Fig. 1. The dihedral angle between the pyridine ring and the phenyl ring is 35.45 (7)°. Intermolecular O—H···O, O—H···N, N—H···O and C—H···O hydrogen bonds are found in the crystal structure. Furthermore, a C22—H22···π interaction involving the pyridine (N1—C6) ring and a C5—H5···π interaction involving the phenyl (C21—C26) ring are also found.

Experimental

Sodium hydroxide (0.4 g, 0.01 mol) in a stoppered conical flask was kept in an ice-cold environment. Ethanol (40 ml) was added to dissolve it and the mixture was stirred continuously using a magnetic stirrer. An equimolar quantity of nicotinic hydrazide (1.371 g, 0.01 mol) and cinnamaldehyde (1.32 g, 0.01 mol) was added to this mixture. The stirring was continued for 5 h in ice-cold conditions. The mixture was kept overnight in a refrigerator. The mixture was then allowed to stand for four days under normal conditions. A yellow solid was obtained. This was filtered, washed and recrystallized from ethanol. Yield 2.3 g, 46.80%.