(E) 4 (Isonicotinoylhydrazono)penta­noic acid monohydrate

organic papers

Acta Cryst.(2006). E62, o1469–o1470 doi:10.1107/S1600536806009573 Wang and Tang _C

11H13N3O3H2O

o1469

Acta Crystallographica Section E Structure Reports Online

ISSN 1600-5368

(

E

)-4-(Isonicotinoylhydrazono)pentanoic

acid monohydrate

Yong-Tao Wang* and Gui-Mei Tang

Department of Chemical Engineering, Shandong Institute of Light Industry, Jinan, Shandong 250100, People’s Republic of China

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study

T= 293 K

Mean(C–C) = 0.004 A˚

Rfactor = 0.080

wRfactor = 0.185

Data-to-parameter ratio = 13.9

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

Received 28 February 2006 Accepted 14 March 2006

#2006 International Union of Crystallography All rights reserved

The title compound, C11H13N3O3H2O, was synthesized by the

reaction of acetopropanoic acid and isonicotinoylhydrazide in ethanol. A three-dimensional network of intermolecular O—

H O, O—H N and N—H O hydrogen bonds stabilizes

the crystal structure.

Comment

Hydrazine and its derivatives exhibit biological and pharma-cological activities (Vicini et al., 2002; Maccari et al., 2005). These compounds are also used as synthetic intermediates (Rollaset al., 2002). The title compound, (I), was synthesized in our laboratory by the reaction of acetopropanoic acid and isonicotinoylhydrazide in an ethanol medium. We present here its crystal structure (Fig. 1).

The bond lengths (Table 1) and angles show normal values. The uncoordinated water molecule plays an important role in the formation of a three-dimensional network of

inter-molecular O—H O and N—H O hydrogen bonds

(Table 2), which stabilize the crystal structure (Fig. 2). O— H N interactions are also present.

Experimental

A mixture of acetopropanoic acid (1.16 mg, 10 mmol) and isonicoti-noylhydrazide (1.37 mg, 10 mmol) was refluxed in ethanol for 3 h. After cooling, the mixture was filtered and dried. The title compound was recrystallized from a mixed solvent of methanol and water (1:5) in 85% yield (200 mg). Block-shaped colourless single crystals suitable for X-ray diffraction were obtained. Analysis found (%): C 52.03, H 5.96, N 16.66; C11H15N3O4requires (%): C 52.17, H 5.97, N

16.59.

Crystal data

C11H13N3O3H2O

Mr= 253.26 Monoclinic,P21=c

a= 9.7834 (14) A˚

b= 12.4798 (17) A˚

c= 10.0924 (15) A˚

= 92.447 (3) V= 1231.1 (3) A˚3

Z= 4

Dx= 1.366 Mg m3

MoKradiation Cell parameters from 6637

reflections

= 2–52

= 0.11 mm1

Data collection

Bruker SMART CCD area-detector diffractometer

’and!scans

Absorption correction: multi-scan (SADABS; Sheldrick, 1996)

Tmin= 0.969,Tmax= 0.979

6637 measured reflections

2425 independent reflections 1674 reflections withI> 2(I)

Rint= 0.038

max= 26.0

h=5!12

k=15!14

l=12!12

Refinement

Refinement onF2

R[F2_{> 2(F}2_{)] = 0.080}

wR(F2_{) = 0.185}

S= 1.23 2425 reflections 175 parameters

H atoms treated by a mixture of independent and constrained refinement

w= 1/[2_(F

o2) + (0.0716P)2

+ 0.1162P]

whereP= (Fo2+ 2Fc2)/3

(/)max< 0.001

max= 0.28 e A˚

3

min=0.29 e A˚

3

Table 1

Selected bond lengths (A˚ ).

O1—C6 1.224 (3) O2—C11 1.321 (4) O3—C11 1.204 (3) N1—C1 1.325 (4)

N1—C5 1.331 (4) N2—C6 1.342 (3) N2—N3 1.396 (3) N3—C7 1.273 (3)

Table 2

Hydrogen-bond geometry (A˚ ,_).

D—H A D—H H A D A D—H A

O1W—H1WA O1i 0.86 (5) 1.92 (5) 2.769 (4) 171 (4) N2—H2 O1W 0.86 2.09 2.869 (3) 151 O1W—H1WB O2ii

0.86 (5) 2.04 (5) 2.887 (3) 168 (4) O2—H2C N1iii 0.85 (4) 1.81 (4) 2.647 (4) 170 (4)

Symmetry codes: (i)x;yþ1

2;zþ12; (ii)x;yþ12;zþ12; (iii)x1;y;z1.

All H atoms were initially located in a difference Fourier map. The O-bound H atoms were refined isotropically. All other H atoms were placed in geometrically idealized positions and refined as riding, with N—H = 0.86 A˚ , C—H = 0.93–0.97 A˚ and Uiso(H) = 1.2Ueq of the

parent atom.

Data collection:SMART(Bruker, 2001); cell refinement:SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:

SHELXTL(Sheldrick, 1999); software used to prepare material for publication:SHELXTL.

YTW acknowledges the financial support of the Starting Fund of Shandong Institute of Light Industry.

References

Bruker (2001).SMARTandSAINT, Bruker AXS Inc., Madison, Wisconsin, USA.

Maccari, R., Ottana`, R. & Vigorita, M. G. (2005).Biol. Med. Chem. Lett.15, 2509–2513.

Rollas, S., Gulerman, N. & Erdeniz, H. (2002).Il Farmaco,57, 171–174. Sheldrick, G. M. (1996).SADABS. University of Go¨ttingen, Germany. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of

Go¨ttingen, Germany.

Sheldrick, G. M. (1999).SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

Vicini, P., Zani, F., Cozzini, P. & Doytchinova, I. (2002).Eur. J. Med. Chem.37, 553–564.

Figure 1

View of (I), showing displacement ellipsoids drawn at the 30% probability level. H atoms are represented by circles of arbitrary size.

Figure 2

supporting information

sup-1

Acta Cryst. (2006). E62, o1469–o1470

supporting information

Acta Cryst. (2006). E62, o1469–o1470 [https://doi.org/10.1107/S1600536806009573]

(

E

)-4-(Isonicotinoylhydrazono)pentanoic acid monohydrate

Yong-Tao Wang and Gui-Mei Tang

(E)-4-(Isonicotinoylhydrazono)pentanoic acid monohydrate

Crystal data

C11H13N3O3·H2O Mr = 253.26

Monoclinic, P21/c

Hall symbol: -P 2ybc a = 9.7834 (14) Å b = 12.4798 (17) Å c = 10.0924 (15) Å β = 92.447 (3)° V = 1231.1 (3) Å3 Z = 4

F(000) = 536 Dx = 1.366 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 6637 reflections θ = 2–52°

µ = 0.11 mm−1 T = 293 K Block, colourless 0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART-CCD area-detector diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

φ and ω scans

Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin = 0.969, Tmax = 0.979

6637 measured reflections 2425 independent reflections 1674 reflections with I > 2σ(I) Rint = 0.038

θmax = 26.0°, θmin = 2.1° h = −5→12

k = −15→14 l = −12→12

Refinement

Refinement on F2

Least-squares matrix: full R[F2 _{> 2σ(F}2_{)] = 0.080} wR(F2_{) = 0.185} S = 1.23 2425 reflections 175 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H atoms treated by a mixture of independent and constrained refinement

w = 1/[σ2_(F

o2) + (0.0716P)2 + 0.1162P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001

Δρmax = 0.28 e Å−3

Special details

Experimental. IR (KBr, ν cm-1_{): 3455, 2899, 2446, 1768, 1611, 1567, 1533, 1423, 1265, 1201, 1021, 841.}

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 F}2_,

conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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₎

x y z Uiso*/Ueq

supporting information

sup-3

Acta Cryst. (2006). E62, o1469–o1470 Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

O1 0.0672 (16) 0.0384 (13) 0.0456 (14) 0.0098 (11) −0.0281 (12) −0.0115 (10) O2 0.0642 (16) 0.0372 (13) 0.0568 (16) 0.0076 (11) −0.0361 (14) −0.0052 (11) O3 0.0624 (16) 0.0416 (13) 0.0621 (16) 0.0027 (11) −0.0353 (13) 0.0074 (11) N1 0.0431 (15) 0.0483 (16) 0.0351 (15) 0.0078 (13) −0.0163 (12) −0.0035 (12) N2 0.0382 (14) 0.0317 (13) 0.0340 (14) 0.0013 (11) −0.0149 (12) −0.0044 (11) N3 0.0379 (14) 0.0369 (14) 0.0325 (14) 0.0021 (11) −0.0160 (12) 0.0000 (11) C1 0.0359 (17) 0.0425 (18) 0.050 (2) −0.0037 (15) −0.0127 (15) −0.0077 (15) C2 0.0371 (18) 0.0371 (17) 0.0458 (19) −0.0010 (14) −0.0139 (15) 0.0010 (14) C3 0.0269 (15) 0.0393 (17) 0.0288 (16) 0.0033 (13) −0.0016 (13) −0.0018 (13) C4 0.046 (2) 0.0409 (18) 0.0376 (18) −0.0008 (15) −0.0117 (15) −0.0027 (14) C5 0.059 (2) 0.0395 (18) 0.043 (2) 0.0038 (16) −0.0153 (17) 0.0046 (15) C6 0.0337 (16) 0.0362 (17) 0.0283 (16) 0.0002 (14) −0.0063 (13) −0.0007 (13) C7 0.0363 (16) 0.0359 (16) 0.0295 (16) 0.0016 (14) −0.0041 (13) 0.0013 (13) C8 0.061 (2) 0.0382 (18) 0.046 (2) −0.0021 (16) −0.0154 (17) 0.0017 (15) C9 0.0460 (19) 0.0434 (18) 0.0366 (18) 0.0032 (15) −0.0137 (15) 0.0022 (14) C10 0.0426 (18) 0.0378 (16) 0.0358 (17) 0.0040 (15) −0.0142 (14) 0.0036 (13) C11 0.0368 (17) 0.0416 (18) 0.0336 (17) 0.0072 (15) −0.0062 (14) 0.0018 (15) O1W 0.097 (2) 0.0398 (15) 0.0345 (15) 0.0043 (14) −0.0126 (14) −0.0008 (11)

Geometric parameters (Å, º)

O1—C6 1.224 (3) C4—C5 1.369 (4) O2—C11 1.321 (4) C4—H4 0.9300 O2—H2C 0.85 (4) C5—H5 0.9300 O3—C11 1.204 (3) C7—C8 1.497 (4) N1—C1 1.325 (4) C7—C9 1.505 (4) N1—C5 1.331 (4) C8—H8A 0.9600 N2—C6 1.342 (3) C8—H8B 0.9600 N2—N3 1.396 (3) C8—H8C 0.9600 N2—H2 0.8600 C9—C10 1.508 (4) N3—C7 1.273 (3) C9—H9A 0.9700 C1—C2 1.376 (4) C9—H9B 0.9700 C1—H1 0.9300 C10—C11 1.499 (4) C2—C3 1.385 (4) C10—H10A 0.9700 C2—H2A 0.9300 C10—H10B 0.9700 C3—C4 1.386 (4) O1W—H1WA 0.86 (5) C3—C6 1.498 (4) O1W—H1WB 0.87 (4)

N1—C1—H1 118.1 H8B—C8—H8C 109.5 C2—C1—H1 118.1 C10—C9—C7 115.6 (3) C1—C2—C3 118.8 (3) C10—C9—H9A 108.4 C1—C2—H2A 120.6 C7—C9—H9A 108.4 C3—C2—H2A 120.6 C10—C9—H9B 108.4 C2—C3—C4 117.7 (3) C7—C9—H9B 108.4 C2—C3—C6 124.8 (3) H9A—C9—H9B 107.4 C4—C3—C6 117.5 (3) C11—C10—C9 112.8 (3) C5—C4—C3 119.0 (3) C11—C10—H10A 109.0 C5—C4—H4 120.5 C9—C10—H10A 109.0 C3—C4—H4 120.5 C11—C10—H10B 109.0 N1—C5—C4 123.7 (3) C9—C10—H10B 109.0 N1—C5—H5 118.2 H10A—C10—H10B 107.8 C4—C5—H5 118.2 O3—C11—O2 122.6 (3) O1—C6—N2 123.4 (3) O3—C11—C10 124.6 (3) O1—C6—C3 119.5 (3) O2—C11—C10 112.8 (3) N2—C6—C3 117.1 (2) H1WA—O1W—H1WB 103 (4) N3—C7—C8 127.1 (3)

C6—N2—N3—C7 −168.6 (3) C2—C3—C6—O1 152.2 (3) C5—N1—C1—C2 0.3 (5) C4—C3—C6—O1 −25.3 (4) N1—C1—C2—C3 −0.1 (5) C2—C3—C6—N2 −26.0 (4) C1—C2—C3—C4 0.3 (4) C4—C3—C6—N2 156.5 (3) C1—C2—C3—C6 −177.2 (3) N2—N3—C7—C8 2.6 (4) C2—C3—C4—C5 −0.5 (4) N2—N3—C7—C9 −178.8 (2) C6—C3—C4—C5 177.1 (3) N3—C7—C9—C10 7.6 (4) C1—N1—C5—C4 −0.6 (5) C8—C7—C9—C10 −173.6 (3) C3—C4—C5—N1 0.7 (5) C7—C9—C10—C11 179.9 (3) N3—N2—C6—O1 4.9 (4) C9—C10—C11—O3 −5.1 (5) N3—N2—C6—C3 −177.0 (2) C9—C10—C11—O2 174.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

O1W—H1WA···O1i _{0.86 (5) 1.92 (5) 2.769 (4) 171 (4)}

N2—H2···O1W 0.86 2.09 2.869 (3) 151 O1W—H1WB···O2ii _{0.86 (5) 2.04 (5) 2.887 (3) 168 (4)}

O2—H2C···N1iii _{0.85 (4) 1.81 (4) 2.647 (4) 170 (4)}

C4—H4···O3iv _{0.93 2.55 3.399 (3) 152}

C8—H8A···O1W 0.96 2.36 3.147 (4) 139 C8—H8A···N2 0.96 2.41 2.817 (3) 105 C8—H8C···O3v _{0.96 2.53 3.411 (4) 153}