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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 69| Part 7| July 2013| Pages o1177-o1178
https://doi.org/10.1107/S1600536813017406

(E)-N′-(4-Meth­­oxy­benzyl­­idene)pyridine-3-carbohydrazide dihydrate

J. Josephine Novina,a G. Vasuki,b* M. Sureshc and M. Syed Ali Padushac

aDepartment of Physics, Idhaya College for Women, Kumbakonam-1, India, bDepartment of Physics, Kunthavai Naachiar Govt. Arts College (W) (Autonomous), Thanjavur-7, India, and cPG & Research Department of Chemistry, Jamal Mohamed College, Tiruchirappalli-20, India
*Correspondence e-mail: vasuki.arasi@yahoo.com

(Received 17 June 2013; accepted 24 June 2013; online 29 June 2013)

In the title compound, C14H13N3O2·2H2O, the hydrazone mol­ecule adopts an E conformation with respect to the C=N bond. The dihedral angle between the benzene and pyridine rings is 8.55 (10)°. The methyl­idene–hydrazide [–C(=O)–N–N=C–] fragment is essentially planar, with a maximum deviation of 0.0375 (13) Å. The mean planes of the benzene and pyridine rings make dihedral angles of 2.71 (14) and 11.25 (13)°, respectively, with mean plane of the methyl­idene-hydrazide fragment. In the crystal, the benzohydrazide and water mol­ecules are linked by N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds into a three-dimensional network.

Related literature

For the biological activity of benzohydrazides, see: Hai-Yun (2011[Hai-Yun, Z. (2011). Chin. J. Struct. Chem. 30, 724-730.]); Havanur et al. (2010[Havanur, V. C., Badiger, D. S., Ligade, S. G. & Gudasi, K. B. (2010). Pharma Chem. 2, 390-404.]); Parashar et al. (2009[Parashar, B., Punjabi, P. B., Gupta, G. D. & Sharma, V. K. (2009). Int. J. Chem. Tech. Res. 1, 1022-1025.]). For details of the ability of benzohydrazone compounds to inhibit cell growth and DNA synthesis, see: Ambwani et al. (2011[Ambwani, J., Dikshit, S. N., Tiwari, V. K., Dubey, A. K. & Rahul, A. (2011). Asian J. Chem. Environ. Res. 4, 33-35.]); Despaigne et al. (2010[Despaigne, A. A. R., Vieira, L. F., Mendes, I. C., da Costa, F. B., Speziali, N. L. & Beraldo, H. (2010). J. Braz. Chem. Soc. 21, 1247-1257.]); Havanur et al. (2010[Havanur, V. C., Badiger, D. S., Ligade, S. G. & Gudasi, K. B. (2010). Pharma Chem. 2, 390-404.]). For background to the use of benzohydrazides as catalysts, see: Seleem et al. (2011[Seleem, H. S., El-Inany, G. A., El-Shetary, B. A., Mousa, M. A. & Hanafy, F. I. (2011). Chem. Cent. J. 5, 1-9.]); Singh & Raghav (2011[Singh, M. & Raghav, N. (2011). Int. J. Pharm. Pharm. Sci. 3, 26-32.]). For related structures, see: Ahmad et al. (2010[Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o976.]); Hu & Liu (2012[Hu, H.-N. & Liu, S.-Y. (2012). Acta Cryst. E68, o1613.]); Shi & Li (2012[Shi, Z.-F. & Li, J.-M. (2012). Acta Cryst. E68, o1726.]).

[Scheme 1]

Experimental

Crystal data

  • C14H13N3O2·2H2O

  • Mr = 291.31

  • Monoclinic, P 21 /n

  • a = 7.6534 (6) Å

  • b = 16.3503 (11) Å

  • c = 11.4887 (6) Å

  • β = 96.889 (2)°

  • V = 1427.26 (17) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 296 K

  • 0.30 × 0.25 × 0.20 mm
Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.970, Tmax = 0.980

  • 11391 measured reflections

  • 3449 independent reflections

  • 2050 reflections with I > 2σ(I)

  • Rint = 0.028
Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.155

  • S = 0.93

  • 3449 reflections

  • 206 parameters

  • 6 restraints

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

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2N2⋯O1W 0.86 2.08 2.9013 (17) 161
O1W—H1O1⋯N3i 0.81 (1) 2.08 (1) 2.8697 (18) 166 (2)
O1W—H2O1⋯O2Wii 0.83 (1) 1.93 (1) 2.749 (2) 171 (2)
O2W—H1O2⋯N1iii 0.83 (2) 2.40 (2) 3.209 (2) 166 (3)
O2W—H2O2⋯O2 0.83 (2) 2.01 (2) 2.8182 (17) 164 (2)
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) -x, -y+2, -z+2; (iii) -x+1, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813017406/sj5336sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813017406/sj5336Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813017406/sj5336Isup3.cml

checkCIF report


Comment top

Hydrazones have attracted much attention for their excellent biological properties, such as antimicrobial, anti-convulsant, analgestic, anti-inflammatory, antiplatelet, antitubercular, anticancer, antitumor (Hai-Yun, 2011), antiviral and vasodilator activities (Parashar et al., 2009). Hydrazones possessing azomethine –NHN═CH– groups constitute an important class of compounds for new drug development (Hai-Yun, 2011). Moreover, hydrazones derived from 2-acetylpyridine are known to inhibit the proliferation of tumour cells to a greater extent compared to standard anticancer agents (Havanur et al., 2010). In addition, metal complexes with hydrazones exhibit antimicrobial, DNA-binding and cytotoxic activities. It has also been shown that these metal complexes can be potent inhibitors of cell growth and DNA synthesis (Despaigne et al., 2010; Havanur et al., 2010; Ambwani et al., 2011). Metal complexes with hydrazones also have potential applications as catalysts, luminescent probes and molecular sensors (Seleem et al., 2011; Singh & Raghav, 2011). We report herein the crystal structure of the title compound, a new hydrazone.

The title compound (Fig. 1), C14H13N3O2.2H2O, comprises one benzohydrazide molecule and two water molecules. The hydrazone molecule adopts an E conformation with respect to the C═N bond with the torsion angle of -177.41 (16)° (C8—N1—N2—C9). Phenyl and pyridine rings (C2—C7 and N3/C10—C14, respectively) are each planner with a dihedral angle 8.55 (10)° between their mean-planes. The methylidenehydrazide fragment O2/C9/N2/N1/C8 in the title compound is essentially planar with maximum deviation being -0.0375 (13) Å for the N1 atom. The mean-planes of the benzene and pyridine rings make dihedral angles of 2.71 (14)° and 11.25 (13)°, respectively, with mean–plane of the methylidenehydrazide fragment. The C8═N1 and C9═O2 bond lengths are 1.270 (2) and 1.2199 (18) Å, respectively, which is very close to the values found in related structures (Hu & Liu, 2012; Shi & Li, 2012; Ahmad et al., 2010). The methoxy group is co–planar with the benzene ring to which it is bound with the C1—O1—C2—C3 torsion angle = -0.26 (27)°.

In the crystal packing (Fig. 2), the molecules of benzohydrazide and water are linked by N2—H2N2···O1W, O1W—H2O1···O2W, O2W—H2O2···O2, O1W—H1O1···N3 and O2W—H1O2···N1 hydrogen bonds (Table 1) into a three–dimensional network.

Related literature top

For the biological activity of benzohydrazides, see: Hai-Yun (2011); Havanur et al. (2010); Parashar et al. (2009). For details of the ability of benzohydrazone compounds to inhibit cell growth and DNA synthesis, see: Ambwani et al. (2011); Despaigne et al. (2010); Havanur et al. (2010). For background to the use of benzohydrazides as catalysts, see: Seleem et al. (2011); Singh & Raghav (2011). For related structures, see: Ahmad et al. (2010); Hu & Liu (2012); Shi & Li (2012).

Experimental top

Anisaldehyde (1.2 ml, 0.01 mol) and benzoic acid hydrazide (1.37 g, 0.01 mol) were added to ethanol(10 ml) of and stirred for an hour in the presence of hydrochloric acid to form a white precipitate. The precipitate was washed with sodium bicarbonate solution and filtered and again washed with petroleum ether (40–60%)and dried in air. The compound was recrystallized from absolute ethanol.

Refinement top

H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H = 0.93 Å, CH3 = 0.96 Å, N—H = 0.86 Å and O—H = 0.81–0.83 Å with Uiso(H) = 1.5Ueq(CH3) and 1.2Ueq(CH, NH).

Structure description top

Hydrazones have attracted much attention for their excellent biological properties, such as antimicrobial, anti-convulsant, analgestic, anti-inflammatory, antiplatelet, antitubercular, anticancer, antitumor (Hai-Yun, 2011), antiviral and vasodilator activities (Parashar et al., 2009). Hydrazones possessing azomethine –NHN═CH– groups constitute an important class of compounds for new drug development (Hai-Yun, 2011). Moreover, hydrazones derived from 2-acetylpyridine are known to inhibit the proliferation of tumour cells to a greater extent compared to standard anticancer agents (Havanur et al., 2010). In addition, metal complexes with hydrazones exhibit antimicrobial, DNA-binding and cytotoxic activities. It has also been shown that these metal complexes can be potent inhibitors of cell growth and DNA synthesis (Despaigne et al., 2010; Havanur et al., 2010; Ambwani et al., 2011). Metal complexes with hydrazones also have potential applications as catalysts, luminescent probes and molecular sensors (Seleem et al., 2011; Singh & Raghav, 2011). We report herein the crystal structure of the title compound, a new hydrazone.

The title compound (Fig. 1), C14H13N3O2.2H2O, comprises one benzohydrazide molecule and two water molecules. The hydrazone molecule adopts an E conformation with respect to the C═N bond with the torsion angle of -177.41 (16)° (C8—N1—N2—C9). Phenyl and pyridine rings (C2—C7 and N3/C10—C14, respectively) are each planner with a dihedral angle 8.55 (10)° between their mean-planes. The methylidenehydrazide fragment O2/C9/N2/N1/C8 in the title compound is essentially planar with maximum deviation being -0.0375 (13) Å for the N1 atom. The mean-planes of the benzene and pyridine rings make dihedral angles of 2.71 (14)° and 11.25 (13)°, respectively, with mean–plane of the methylidenehydrazide fragment. The C8═N1 and C9═O2 bond lengths are 1.270 (2) and 1.2199 (18) Å, respectively, which is very close to the values found in related structures (Hu & Liu, 2012; Shi & Li, 2012; Ahmad et al., 2010). The methoxy group is co–planar with the benzene ring to which it is bound with the C1—O1—C2—C3 torsion angle = -0.26 (27)°.

In the crystal packing (Fig. 2), the molecules of benzohydrazide and water are linked by N2—H2N2···O1W, O1W—H2O1···O2W, O2W—H2O2···O2, O1W—H1O1···N3 and O2W—H1O2···N1 hydrogen bonds (Table 1) into a three–dimensional network.

For the biological activity of benzohydrazides, see: Hai-Yun (2011); Havanur et al. (2010); Parashar et al. (2009). For details of the ability of benzohydrazone compounds to inhibit cell growth and DNA synthesis, see: Ambwani et al. (2011); Despaigne et al. (2010); Havanur et al. (2010). For background to the use of benzohydrazides as catalysts, see: Seleem et al. (2011); Singh & Raghav (2011). For related structures, see: Ahmad et al. (2010); Hu & Liu (2012); Shi & Li (2012).

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: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Crystal packing of the title compound viewed along the a axis. Hydrogen bonds are shown as dashed lines.
(E)-N'-(4-Methoxybenzylidene)pyridine-3-carbohydrazide dihydrate top
Crystal data top
C14H13N3O2·2H2OF(000) = 616
Mr = 291.31Dx = 1.356 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2772 reflections
a = 7.6534 (6) Åθ = 5.0–49.6°
b = 16.3503 (11) ŵ = 0.10 mm−1
c = 11.4887 (6) ÅT = 296 K
β = 96.889 (2)°Block, colorless
V = 1427.26 (17) Å30.30 × 0.25 × 0.20 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer		3449 independent reflections
Radiation source: fine-focus sealed tube2050 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω and φ scanθmax = 28.2°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		h = −6→10
Tmin = 0.970, Tmax = 0.980k = −21→21
11391 measured reflectionsl = −13→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)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.155 w = 1/[σ2(Fo2) + (0.0961P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max = 0.001
3449 reflectionsΔρmax = 0.21 e Å−3
206 parametersΔρmin = −0.17 e Å−3
6 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.009 (2)
Crystal data top
C14H13N3O2·2H2OV = 1427.26 (17) Å3
Mr = 291.31Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.6534 (6) ŵ = 0.10 mm−1
b = 16.3503 (11) ÅT = 296 K
c = 11.4887 (6) Å0.30 × 0.25 × 0.20 mm
β = 96.889 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer		3449 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		2050 reflections with I > 2σ(I)
Tmin = 0.970, Tmax = 0.980Rint = 0.028
11391 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0466 restraints
wR(F2) = 0.155H atoms treated by a mixture of independent and constrained refinement
S = 0.93Δρmax = 0.21 e Å−3
3449 reflectionsΔρmin = −0.17 e Å−3
206 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
O1W−0.21558 (17)0.92875 (9)0.70457 (12)0.0661 (4)
O10.21045 (18)1.39338 (7)0.86316 (12)0.0652 (4)
O2W0.4378 (2)1.01711 (9)1.14079 (13)0.0670 (4)
N10.15479 (18)1.00258 (8)0.89482 (11)0.0459 (4)
N20.09417 (18)0.92297 (7)0.87676 (11)0.0449 (4)
H2N20.00610.91210.82530.054*
N30.1583 (2)0.63790 (8)0.97900 (12)0.0530 (4)
O20.29733 (18)0.87747 (7)1.01980 (11)0.0688 (5)
C10.3384 (3)1.42723 (12)0.9485 (2)0.0717 (6)
H1A0.30711.41581.02530.108*
H1B0.34381.48530.93750.108*
H1C0.45121.40350.94080.108*
C20.1867 (2)1.31049 (10)0.86152 (14)0.0470 (4)
C30.2804 (2)1.25610 (10)0.93809 (15)0.0477 (4)
H30.36711.27530.99520.057*
C40.2445 (2)1.17334 (10)0.92929 (14)0.0460 (4)
H40.30801.13720.98060.055*
C50.1152 (2)1.14332 (9)0.84510 (13)0.0413 (4)
C80.0684 (2)1.05745 (10)0.83445 (14)0.0450 (4)
H8−0.02781.04210.78180.054*
C90.1777 (2)0.86340 (9)0.94232 (13)0.0422 (4)
C100.1187 (2)0.77765 (9)0.91597 (13)0.0384 (4)
C140.1898 (2)0.71787 (10)0.99233 (13)0.0467 (4)
H140.26500.73451.05770.056*
C130.0525 (2)0.61574 (10)0.88326 (15)0.0520 (5)
H130.03030.56030.87080.062*
C60.0240 (2)1.19971 (10)0.76869 (14)0.0482 (4)
H6−0.06291.18090.71140.058*
C70.0592 (2)1.28169 (10)0.77585 (15)0.0509 (4)
H7−0.00221.31780.72340.061*
C12−0.0253 (2)0.67021 (10)0.80237 (15)0.0519 (5)
H12−0.09880.65190.73730.062*
C110.0072 (2)0.75257 (9)0.81904 (14)0.0456 (4)
H11−0.04520.79070.76580.055*
H1O1−0.266 (2)0.9158 (11)0.6408 (10)0.068*
H2O1−0.291 (2)0.9418 (13)0.7474 (13)0.068*
H2O20.389 (3)0.9826 (11)1.0949 (17)0.077 (7)*
H1O20.544 (2)1.021 (2)1.134 (3)0.149 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1W0.0546 (9)0.0784 (9)0.0607 (9)−0.0029 (7)−0.0121 (7)−0.0218 (7)
O10.0764 (10)0.0408 (7)0.0760 (9)−0.0070 (6)−0.0009 (8)0.0042 (6)
O2W0.0648 (10)0.0722 (9)0.0623 (9)−0.0155 (8)0.0000 (8)−0.0202 (7)
N10.0494 (8)0.0396 (7)0.0464 (8)−0.0076 (6)−0.0043 (7)−0.0017 (6)
N20.0468 (8)0.0403 (7)0.0440 (8)−0.0064 (6)−0.0088 (6)−0.0030 (6)
N30.0636 (10)0.0439 (8)0.0487 (8)−0.0001 (7)−0.0054 (7)0.0017 (6)
O20.0731 (9)0.0519 (7)0.0702 (9)−0.0125 (6)−0.0370 (8)0.0024 (6)
C10.0695 (14)0.0482 (10)0.0957 (16)−0.0127 (9)0.0025 (12)−0.0117 (10)
C20.0523 (10)0.0401 (9)0.0497 (9)−0.0011 (7)0.0111 (8)−0.0009 (7)
C30.0489 (10)0.0472 (9)0.0450 (9)−0.0052 (7)−0.0023 (8)−0.0042 (7)
C40.0500 (10)0.0418 (9)0.0439 (9)0.0017 (7)−0.0030 (8)0.0007 (7)
C50.0427 (9)0.0420 (8)0.0386 (8)−0.0005 (7)0.0022 (7)−0.0033 (6)
C80.0447 (9)0.0457 (9)0.0420 (9)−0.0029 (7)−0.0049 (7)−0.0037 (7)
C90.0428 (9)0.0436 (9)0.0383 (8)−0.0055 (7)−0.0026 (7)−0.0010 (6)
C100.0380 (8)0.0421 (8)0.0343 (8)−0.0016 (7)0.0009 (7)−0.0026 (6)
C140.0518 (10)0.0479 (9)0.0375 (9)−0.0021 (8)−0.0068 (8)−0.0020 (7)
C130.0578 (11)0.0413 (9)0.0546 (10)−0.0017 (8)−0.0021 (9)−0.0064 (7)
C60.0478 (10)0.0500 (10)0.0441 (9)0.0022 (8)−0.0062 (8)−0.0028 (7)
C70.0554 (11)0.0477 (9)0.0480 (9)0.0074 (8)−0.0003 (8)0.0046 (7)
C120.0555 (11)0.0484 (9)0.0478 (9)−0.0034 (8)−0.0100 (8)−0.0096 (8)
C110.0486 (10)0.0442 (9)0.0412 (9)0.0013 (7)−0.0068 (8)0.0003 (7)
Geometric parameters (Å, º) top
O1W—H1O10.814 (9)C3—H30.9300
O1W—H2O10.828 (9)C4—C51.388 (2)
O1—C21.3672 (19)C4—H40.9300
O1—C11.413 (2)C5—C61.400 (2)
O2W—H2O20.830 (15)C5—C81.450 (2)
O2W—H1O20.828 (17)C8—H80.9300
N1—C81.270 (2)C9—C101.493 (2)
N1—N21.3890 (17)C10—C111.382 (2)
N2—C91.3451 (19)C10—C141.381 (2)
N2—H2N20.8600C14—H140.9300
N3—C141.335 (2)C13—C121.370 (2)
N3—C131.335 (2)C13—H130.9300
O2—C91.2199 (18)C6—C71.368 (2)
C1—H1A0.9600C6—H60.9300
C1—H1B0.9600C7—H70.9300
C1—H1C0.9600C12—C111.379 (2)
C2—C71.383 (2)C12—H120.9300
C2—C31.388 (2)C11—H110.9300
C3—C41.382 (2)
H1O1—O1W—H2O1108.4 (17)N1—C8—H8119.0
C2—O1—C1118.54 (14)C5—C8—H8119.0
H2O2—O2W—H1O2111 (2)O2—C9—N2122.46 (14)
C8—N1—N2115.97 (13)O2—C9—C10120.50 (14)
C9—N2—N1117.85 (12)N2—C9—C10117.04 (13)
C9—N2—H2N2121.1C11—C10—C14117.41 (14)
N1—N2—H2N2121.1C11—C10—C9125.79 (14)
C14—N3—C13116.33 (13)C14—C10—C9116.70 (13)
O1—C1—H1A109.5N3—C14—C10124.64 (14)
O1—C1—H1B109.5N3—C14—H14117.7
H1A—C1—H1B109.5C10—C14—H14117.7
O1—C1—H1C109.5N3—C13—C12123.60 (15)
H1A—C1—H1C109.5N3—C13—H13118.2
H1B—C1—H1C109.5C12—C13—H13118.2
O1—C2—C7115.38 (14)C7—C6—C5121.87 (14)
O1—C2—C3124.65 (14)C7—C6—H6119.1
C7—C2—C3119.97 (14)C5—C6—H6119.1
C4—C3—C2119.85 (14)C6—C7—C2119.58 (15)
C4—C3—H3120.1C6—C7—H7120.2
C2—C3—H3120.1C2—C7—H7120.2
C3—C4—C5121.08 (14)C13—C12—C11118.95 (14)
C3—C4—H4119.5C13—C12—H12120.5
C5—C4—H4119.5C11—C12—H12120.5
C4—C5—C6117.64 (14)C12—C11—C10119.05 (14)
C4—C5—C8123.31 (14)C12—C11—H11120.5
C6—C5—C8119.04 (13)C10—C11—H11120.5
N1—C8—C5122.07 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N2···O1W0.862.082.9013 (17)161
O1W—H1O1···N3i0.81 (1)2.08 (1)2.8697 (18)166 (2)
O1W—H2O1···O2Wii0.83 (1)1.93 (1)2.749 (2)171 (2)
O2W—H1O2···N1iii0.83 (2)2.40 (2)3.209 (2)166 (3)
O2W—H2O2···O20.83 (2)2.01 (2)2.8182 (17)164 (2)
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) −x, −y+2, −z+2; (iii) −x+1, −y+2, −z+2.

Experimental details

Crystal data
Chemical formulaC14H13N3O2·2H2O
Mr291.31
Crystal system, space groupMonoclinic, P21/n
Temperature (K)296
a, b, c (Å)7.6534 (6), 16.3503 (11), 11.4887 (6)
β (°) 96.889 (2)
V (Å3)1427.26 (17)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerBruker Kappa APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.970, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections		11391, 3449, 2050
Rint0.028
(sin θ/λ)max (Å−1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.155, 0.93
No. of reflections3449
No. of parameters206
No. of restraints6
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.21, −0.17

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N2···O1W0.862.082.9013 (17)160.5
O1W—H1O1···N3i0.814 (9)2.075 (10)2.8697 (18)165.5 (18)
O1W—H2O1···O2Wii0.828 (9)1.928 (10)2.749 (2)171.3 (19)
O2W—H1O2···N1iii0.828 (17)2.400 (19)3.209 (2)166 (3)
O2W—H2O2···O20.830 (15)2.012 (16)2.8182 (17)164 (2)
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) −x, −y+2, −z+2; (iii) −x+1, −y+2, −z+2.
 

Acknowledgements

The authors thank the Sophisticated Analytical Instrument Facility, STIC, Cochin University of Science & Technology, Cochin, for the data collection.

References

First citationAhmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o976.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationAltomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  CrossRef Web of Science IUCr Journals Google Scholar
 First citationAmbwani, J., Dikshit, S. N., Tiwari, V. K., Dubey, A. K. & Rahul, A. (2011). Asian J. Chem. Environ. Res. 4, 33–35.  CAS Google Scholar
 First citationBruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationDespaigne, A. A. R., Vieira, L. F., Mendes, I. C., da Costa, F. B., Speziali, N. L. & Beraldo, H. (2010). J. Braz. Chem. Soc. 21, 1247–1257.  Web of Science CSD CrossRef CAS Google Scholar
 First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationHai-Yun, Z. (2011). Chin. J. Struct. Chem. 30, 724–730.  Google Scholar
 First citationHavanur, V. C., Badiger, D. S., Ligade, S. G. & Gudasi, K. B. (2010). Pharma Chem. 2, 390–404.  CAS Google Scholar
 First citationHu, H.-N. & Liu, S.-Y. (2012). Acta Cryst. E68, o1613.  CSD CrossRef IUCr Journals Google Scholar
 First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationParashar, B., Punjabi, P. B., Gupta, G. D. & Sharma, V. K. (2009). Int. J. Chem. Tech. Res. 1, 1022–1025.  CAS Google Scholar
 First citationSeleem, H. S., El-Inany, G. A., El-Shetary, B. A., Mousa, M. A. & Hanafy, F. I. (2011). Chem. Cent. J. 5, 1–9.  Web of Science PubMed Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationShi, Z.-F. & Li, J.-M. (2012). Acta Cryst. E68, o1726.  CSD CrossRef IUCr Journals Google Scholar
 First citationSingh, M. & Raghav, N. (2011). Int. J. Pharm. Pharm. Sci. 3, 26–32.  Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 69| Part 7| July 2013| Pages o1177-o1178
https://doi.org/10.1107/S1600536813017406
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