N′-(2-Methyl-3-phenyl­allyl­idene)nicotinohydrazide monohydrate

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

doi:10.1107/S1600536809023368

. 2009 Jun 20;65(Pt 7):o1659. doi: 10.1107/S1600536809023368

N′-(2-Methyl-3-phenylallylidene)nicotinohydrazide monohydrate

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

PMCID: PMC2969494 PMID: 21582921

Abstract

The asymmetric unit of the title compound, C₁₆H₁₅N₃O·H₂O, contains an N′-(2-methyl-3-phenylallylidene)nicotinohydrazide molecule and a water solvent molecule. The dihedral angle between the pyridine ring and the phenyl ring is 47.26 (5)°. Intermolecular O—H⋯N, O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds are found in the crystal structure. Furthermore, C—H⋯π interactions involving the pyridine and phenyl rings are also found.

Related literature

For a related crystal structure, see: Bao (2008 ▶). For chemical and biological applications of related compounds, see: Moraweck et al. (1997 ▶); Kwon et al. (1996 ▶); Lee et al. (1999 ▶).

Experimental

Crystal data

C₁₆H₁₅N₃O·H₂O
M _r = 283.33
Monoclinic,
a = 9.6821 (4) Å
b = 9.4178 (4) Å
c = 16.0958 (6) Å
β = 98.250 (4)°
V = 1452.49 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 110 K
0.51 × 0.42 × 0.36 mm

Data collection

Oxford Diffraction Gemini R diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T _min = 0.938, T _max = 1.000 (expected range = 0.909–0.969)
10476 measured reflections
4824 independent reflections
3467 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.119
S = 1.02
4824 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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/S1600536809023368/wn2333sup1.cif

e-65-o1659-sup1.cif^{(23KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023368/wn2333Isup2.hkl

e-65-o1659-Isup2.hkl^{(231.5KB, 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⋯N1ⁱ	0.917 (17)	1.987 (17)	2.9033 (11)	177.3 (16)
O1W—H2W⋯O7	0.851 (17)	2.161 (17)	2.9089 (10)	146.5 (15)
O1W—H2W⋯N9	0.851 (17)	2.507 (17)	3.2233 (11)	142.5 (14)
N8—H8⋯O1Wⁱⁱ	0.882 (14)	2.029 (14)	2.8925 (12)	166.0 (13)
C2—H2⋯O7ⁱ	0.95	2.54	3.4021 (12)	151
C10—H10⋯O1Wⁱⁱ	0.95	2.59	3.3781 (13)	140
C13—H13B⋯O1W	0.98	2.55	3.3815 (14)	143
C26—H26⋯O7ⁱⁱⁱ	0.95	2.54	3.4771 (13)	170
C13—H13C⋯Cg1^iv	0.98	2.72	3.5630 (13)	144
C5—H5⋯Cg2^v	0.95	2.57	3.4378 (11)	152

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) . Cg1 and Cg2 are the centroids of the pyridine and benzene 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

Cinnamaldehyde is of importance in the manufacture of fine chemicals, particularly with regard to fragrances and flavorings (Moraweck et al., 1997). 2'-Hydroxycinnamaldehyde was isolated from the stem bark of Cinnamomum cassia and reported to have an inhibitory effect on farnesyl protein transferase activity; it also inhibited the proliferation of several human cancer cell lines including breast, leukemia, ovarian, lung, and colon tumor cells. Nicotinic hydrazide is used as a medicine for key diseases such as leprosy (Hansen's disease), typhoid and tuberculosis (Kwon et al., 1996; Lee et al., 1999). As part of our research, we have synthesized the title compound and report its crystal structure here. Bao (2008) has reported a related crystal structure, viz. N'-(3-phenylallylidene)isonicotinohydrazide.

The molecular structure of the asymmetric unit is shown in Fig. 1. The dihedral angle between the pyridine ring and the phenyl ring is 47.26 (5)°. Intermolecular O—H···N, O—H···O, N—H···O and C—H···O hydrogen bonds are found in the crystal structure. Furthermore, a C13—H13C···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 α-methyl-trans-cinnamaldehyde (1.461 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 2.2 g, 48.47%.