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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 64| Part 1| January 2008| Pages o302-o303
https://doi.org/10.1107/S160053680706655X

Nicotinohydrazide

Jacks P. Priebe,a Renata S. Mello,a Faruk Nomea and Adailton J. Bortoluzzia*

aDepto. de Química, Universidade Federal de Santa Catarina, 88040-900 Florianópolis, Santa Catarina, Brazil
*Correspondence e-mail: adajb@qmc.ufsc.br

(Received 25 October 2007; accepted 11 December 2007; online 18 December 2007)

The title mol­ecule (alternative name: pyridine-3-carbohydrazide; C6H7N3O) was obtained from the reaction of ethyl nicotinate with hydrazine hydrate in methanol. In the amide group, the C—N bond is relatively short, suggesting some degree of electronic delocalization in the mol­ecule. The stabilized conformation may be compared with those of isomeric compounds picolinohydrazide (pyridine-2-carbohydrazide) and isonicotinohydrazide (pyridine-4-carbohydrazide). In the title isomer, the pyridine ring forms an angle of 33.79 (9)° with the plane of the non-H atoms of the hydrazide group. This lack of coplanarity between the hydrazide functionality and the pyridine ring is considerably greater than that observed in isonicotinohydrazide (dihedral angle = 17.14°), while picolinohydrazide is almost fully planar. The title isomer forms inter­molecular N—H⋯O and N—H⋯N hydrogen bonds, which stabilize the crystal structure.

Related literature

The structure of the same compound has been determined independently and is reported in the following paper (Portalone & Colapietro, 2008[Portalone, G. & Colapietro, M. (2008). Acta Cryst. E64, o304.]). The structures of picolinohydrazide (Zareef et al., 2006[Zareef, M., Iqbla, R., Zaidi, J. H., Qadeer, G., Wong, W. Y. & Akhtar, H. (2006). Z. Kristallogr. New Cryst. Struct. 221, 307-308.]) and isonicotinohydrazide (Jensen, 1954[Jensen, L. H. (1954). J. Am. Chem. Soc. 76, 4663-4667.]; Bhat et al., 1974) have been published. For related literature on the biological activity of these mol­ecules, see: Ouelleta et al. (2004[Ouelleta, M., Aitkenb, S. M., Englishc, A. M. & Percivala, M. D. (2004). Arch. Biochem. Biophys. 431, 107-118.]); Zhao et al. (2007[Zhao, X., Yu, S. & Magliozzo, R. S. (2007). Biochemistry, 46, 3161-3170.]). For related literature, see: Bhat et al. (1974[Bhat, T. N., Singh, T. P. & Vijayan, M. (1974). Acta Cryst. B30, 2921-2922.]); Zareef et al. (2006[Zareef, M., Iqbla, R., Zaidi, J. H., Qadeer, G., Wong, W. Y. & Akhtar, H. (2006). Z. Kristallogr. New Cryst. Struct. 221, 307-308.]).

[Scheme 1]

Experimental

Crystal data

  • C6H7N3O

  • Mr = 137.15

  • Orthorhombic, P 21 21 21

  • a = 3.8855 (7) Å

  • b = 10.5191 (5) Å

  • c = 15.9058 (9) Å

  • V = 650.10 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 (2) K

  • 0.46 × 0.30 × 0.20 mm
Data collection

  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: none

  • 1534 measured reflections

  • 1051 independent reflections

  • 866 reflections with I > 2σ(I)

  • Rint = 0.015

  • 3 standard reflections every 200 reflections intensity decay: <1%
Refinement

  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.087

  • S = 1.09

  • 1051 reflections

  • 92 parameters

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2N⋯N1i 0.88 2.11 2.975 (2) 166
N3—H3NA⋯O1ii 0.87 2.22 3.045 (2) 157
N3—H3NB⋯O1iii 0.85 2.55 3.155 (2) 130
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (iii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1].

Table 2
Selected bond lengths (Å) of nicotinohydrazide (I), picolinic acid hydrazide (II) and isonicotinohydrazide (III)

  (I) (II) (III)
N2—N3 1.418 (2) 1.422 1.429
C6—N2 1.335 (2) 1.334 1.346
C6—O1 1.231 (2) 1.235 1.235
C6—C2 1.503 (2) 1.507 1.513

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Version 5.1/1.2. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: HELENA (Spek, 1996[Spek, A. L. (1996). HELENA. University of Utrecht, The Netherlands.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680706655X/bh2145sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680706655X/bh2145Isup2.hkl

checkCIF report


Comment top

The importance of aromatic hydrazides is closely related to their biological activity and to the fact that they can be used for the syntheses of several other biologically active compounds. Nicotinohydrazide, (I), for example, is an efficient peroxidase-activated inhibitor of the POX activity of PGHS-2 (Ouelleta et al., 2004). On the other hand, the isomer isonicotinohydrazide, (III, scheme 2), is not a potent inhibitor, with an IC50 of 129 mM against 15 mM for (I).

Structure also plays a major role in the activity of the anti-tuberculosis drug isonicotinohydrazide, which requires Mycobacterium tuberculosis catalase-peroxidase (KatG) activation to produce an acyl-NAD adduct (Zhao et al., 2007). This adduct is of extreme importance since it is an inhibitor of the enoyl reductase (Mtb InhA), essential for the biosynthesis of acids present in mycobacterial cell walls. Picolinohydrazide, (II), and isonicotinohydrazide, (III), generate the hydrazide-NAD adduct in this system, while nicotinohydrazide, (I), does not. However, the yield of the (II)-NAD adduct is around 35% of that of the (III)-NAD adduct. As a result, (III) is a potent antituberculosis drug, while (I) and (II) are not.

In this context, studies of structural analogues of these biologically active compounds become fundamental and will be useful in elucidating the mechanism of action, which strongly depends on substrate selection and binding stoichiometry to the (III) binding site in KatG, which still has not been completely elucidated.

The crystal structures of picolinohydrazide, (II) (Zareef et al., 2006), and isonicotinohydrazide, (III) (Jensen, 1954; Bhat et al., 1974), have been previously reported and the structure of nicotinohydrazide (I) is here described. The three isomeric hydrazides are distinguished by just the position of the N atom in the pyridine ring with respect to hydrazide group (scheme 2). A selection of their structural parameters is shown in Table 2.

When the structural parameters of isomeric hydrazides are compared, some interesting aspects can be observed, which depend on the structural relation between the N atom in the ring and the hydrazide group. Indeed, while (II) crystallizes in the monoclinic system, isomers (I) and (III) crystallize in the orthorhombic system. The C6?O1 bond length in (I) and also in (II) and (III) are smaller than those usually observed in carboxylic acids (1.365 Å, Zareef et al., 2006). Similarly, the C6—N2 bond distance observed in (I) is consistent with those reported for (II) and (III) hydrazides, suggesting a significant partial double-bond character; the bond lengths are consistent with resonance hybrids between a polar and a neutral form (Bhat et al., 1974). Similar to the results reported (Bhat et al., 1974) for isonicotinohydrazide, the N2—N3 and C2—C6 bonds of (II) have distances similar to their corresponding single bonds. In (I), the pyridine ring bond lengths are very similar to those obtained in related compounds and the ring lies in a plane which forms an angle of 33.79 (9)° with that of the non-H atoms in the hydrazide group. This lack of coplanarity between the hydrazide functionality and the pyridine ring is considerably greater than that observed in isonicotinohydrazide (-17.14°), while picolinohydrazide is almost fully planar, probably because in (II) N2 is in the same side and therefore closer to N1, favoring intramolecular N2—H···N1 hydrogen bond. Conversely, in the crystal structure of (I) N2 and N1 are on opposite sides of the molecule, and in this case only intermolecular hydrogen bonding takes place. The intermolecular hydrogen bonds N3—H···O1 and N2—H···N1 (Table 1), which form a three-dimensional polymeric structure (Fig. 2) are fundamental for the stability of the crystal structure of (I).

Related literature top

The structure of the same compound has been determined independently and is reported in the following paper (Portalone & Colapietro, 2008). The structures of picolinohydrazide (Zareef et al., 2006) and isonicotinohydrazide (Jensen, 1954; Bhat et al., 1974) have been published. For related literature about biological activity of these molecules, see: Ouelleta et al. (2004); Zhao et al. (2007). For related literature, see: Bhat et al. (1974); Zareef et al. (2006).

Experimental top

Nicotinic acid hydrazine was synthesized by the reaction of ethyl nicotinate (43.9 mmol) and hydrazine hydrate 99% (27.5 mmol) in methanol. The reaction mixture was refluxed for 24 h., yielding a yellow solution. Upon cooling to 298 K, the product precipitated and it was washed with methanol and filtered. Colorless needle shaped crystals of (I) suitable for X-ray analysis were grown by recrystallization from a chloroform-methanol (9:1) solution by slow evaporation at room temperature.

Refinement top

All non-H atoms were refined with anisotropic displacement parameters. H atoms attached to C atoms were added at their calculated positions, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(carrier C). H atoms of the hydrazide group were found in a difference map and treated with a riding model and with Uiso(H) = 1.2Ueq(carrier N). In the absence of significant anomalous scattering effects, no Friedel pairs were collected.

Structure description top

The importance of aromatic hydrazides is closely related to their biological activity and to the fact that they can be used for the syntheses of several other biologically active compounds. Nicotinohydrazide, (I), for example, is an efficient peroxidase-activated inhibitor of the POX activity of PGHS-2 (Ouelleta et al., 2004). On the other hand, the isomer isonicotinohydrazide, (III, scheme 2), is not a potent inhibitor, with an IC50 of 129 mM against 15 mM for (I).

Structure also plays a major role in the activity of the anti-tuberculosis drug isonicotinohydrazide, which requires Mycobacterium tuberculosis catalase-peroxidase (KatG) activation to produce an acyl-NAD adduct (Zhao et al., 2007). This adduct is of extreme importance since it is an inhibitor of the enoyl reductase (Mtb InhA), essential for the biosynthesis of acids present in mycobacterial cell walls. Picolinohydrazide, (II), and isonicotinohydrazide, (III), generate the hydrazide-NAD adduct in this system, while nicotinohydrazide, (I), does not. However, the yield of the (II)-NAD adduct is around 35% of that of the (III)-NAD adduct. As a result, (III) is a potent antituberculosis drug, while (I) and (II) are not.

In this context, studies of structural analogues of these biologically active compounds become fundamental and will be useful in elucidating the mechanism of action, which strongly depends on substrate selection and binding stoichiometry to the (III) binding site in KatG, which still has not been completely elucidated.

The crystal structures of picolinohydrazide, (II) (Zareef et al., 2006), and isonicotinohydrazide, (III) (Jensen, 1954; Bhat et al., 1974), have been previously reported and the structure of nicotinohydrazide (I) is here described. The three isomeric hydrazides are distinguished by just the position of the N atom in the pyridine ring with respect to hydrazide group (scheme 2). A selection of their structural parameters is shown in Table 2.

When the structural parameters of isomeric hydrazides are compared, some interesting aspects can be observed, which depend on the structural relation between the N atom in the ring and the hydrazide group. Indeed, while (II) crystallizes in the monoclinic system, isomers (I) and (III) crystallize in the orthorhombic system. The C6?O1 bond length in (I) and also in (II) and (III) are smaller than those usually observed in carboxylic acids (1.365 Å, Zareef et al., 2006). Similarly, the C6—N2 bond distance observed in (I) is consistent with those reported for (II) and (III) hydrazides, suggesting a significant partial double-bond character; the bond lengths are consistent with resonance hybrids between a polar and a neutral form (Bhat et al., 1974). Similar to the results reported (Bhat et al., 1974) for isonicotinohydrazide, the N2—N3 and C2—C6 bonds of (II) have distances similar to their corresponding single bonds. In (I), the pyridine ring bond lengths are very similar to those obtained in related compounds and the ring lies in a plane which forms an angle of 33.79 (9)° with that of the non-H atoms in the hydrazide group. This lack of coplanarity between the hydrazide functionality and the pyridine ring is considerably greater than that observed in isonicotinohydrazide (-17.14°), while picolinohydrazide is almost fully planar, probably because in (II) N2 is in the same side and therefore closer to N1, favoring intramolecular N2—H···N1 hydrogen bond. Conversely, in the crystal structure of (I) N2 and N1 are on opposite sides of the molecule, and in this case only intermolecular hydrogen bonding takes place. The intermolecular hydrogen bonds N3—H···O1 and N2—H···N1 (Table 1), which form a three-dimensional polymeric structure (Fig. 2) are fundamental for the stability of the crystal structure of (I).

The structure of the same compound has been determined independently and is reported in the following paper (Portalone & Colapietro, 2008). The structures of picolinohydrazide (Zareef et al., 2006) and isonicotinohydrazide (Jensen, 1954; Bhat et al., 1974) have been published. For related literature about biological activity of these molecules, see: Ouelleta et al. (2004); Zhao et al. (2007). For related literature, see: Bhat et al. (1974); Zareef et al. (2006).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: HELENA (Spek, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with labeling scheme. Displacement ellipsoids are shown at the 40% probability level.
[Figure 2] Fig. 2. Packing of (I) showing the molecules connected through hydrogen bonds and stacked along [100].
[Figure 3] Fig. 3. The structures of (I)–(III).
Pyridine-3-carbohydrazide top
Crystal data top
C6H7N3OF(000) = 288
Mr = 137.15Dx = 1.401 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 3.8855 (7) Åθ = 5.5–18.7°
b = 10.5191 (5) ŵ = 0.10 mm−1
c = 15.9058 (9) ÅT = 293 K
V = 650.10 (13) Å3Prismatic, colourless
Z = 40.46 × 0.30 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.015
Radiation source: fine-focus sealed tubeθmax = 29.0°, θmin = 2.3°
Graphite monochromatorh = −5→2
ω–2θ scansk = −14→0
1534 measured reflectionsl = −21→0
1051 independent reflections3 standard reflections every 200 reflections
866 reflections with I > 2σ(I) intensity decay: <1%
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)] = 0.031H-atom parameters constrained
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0344P)2 + 0.1144P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
1051 reflectionsΔρmax = 0.18 e Å−3
92 parametersΔρmin = −0.15 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.040 (6)
Crystal data top
C6H7N3OV = 650.10 (13) Å3
Mr = 137.15Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 3.8855 (7) ŵ = 0.10 mm−1
b = 10.5191 (5) ÅT = 293 K
c = 15.9058 (9) Å0.46 × 0.30 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.015
1534 measured reflections3 standard reflections every 200 reflections
1051 independent reflections intensity decay: <1%
866 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.087H-atom parameters constrained
S = 1.09Δρmax = 0.18 e Å−3
1051 reflectionsΔρmin = −0.15 e Å−3
92 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3825 (5)0.84759 (16)0.25136 (11)0.0373 (4)
H10.40070.90920.29300.045*
C20.2298 (5)0.73203 (14)0.27215 (10)0.0319 (4)
C30.2025 (5)0.64013 (16)0.20969 (10)0.0382 (4)
H30.10290.56170.22120.046*
C40.3262 (6)0.66735 (19)0.12995 (11)0.0455 (5)
H40.31140.60760.08700.055*
C50.4720 (7)0.78517 (19)0.11576 (11)0.0472 (5)
H50.55240.80320.06200.057*
C60.0965 (5)0.71648 (17)0.36028 (10)0.0344 (4)
N10.5043 (5)0.87491 (14)0.17489 (10)0.0440 (4)
N20.1167 (5)0.59906 (15)0.39179 (9)0.0405 (4)
H2N0.21550.53650.36370.049*
N3−0.0001 (5)0.56759 (16)0.47365 (9)0.0472 (4)
H3NA0.08770.61890.51120.057*
H3NB−0.21010.58760.47840.057*
O1−0.0227 (5)0.80795 (12)0.39876 (8)0.0487 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0405 (9)0.0307 (7)0.0405 (9)0.0021 (8)−0.0023 (8)−0.0007 (6)
C20.0312 (8)0.0314 (7)0.0330 (7)0.0041 (8)−0.0025 (7)−0.0001 (6)
C30.0445 (11)0.0316 (8)0.0384 (8)0.0007 (8)−0.0049 (8)−0.0009 (7)
C40.0594 (14)0.0442 (9)0.0328 (8)0.0060 (11)−0.0039 (9)−0.0057 (7)
C50.0550 (13)0.0522 (10)0.0345 (8)0.0062 (11)0.0050 (9)0.0069 (8)
C60.0324 (9)0.0367 (8)0.0339 (7)0.0012 (8)−0.0035 (7)−0.0040 (7)
N10.0481 (10)0.0388 (7)0.0451 (8)0.0002 (8)0.0019 (8)0.0078 (6)
N20.0505 (10)0.0373 (7)0.0337 (7)0.0027 (7)0.0057 (7)0.0007 (6)
N30.0557 (11)0.0519 (9)0.0338 (7)−0.0021 (10)0.0028 (8)0.0045 (6)
O10.0604 (10)0.0447 (7)0.0409 (6)0.0120 (7)0.0060 (7)−0.0060 (5)
Geometric parameters (Å, º) top
C1—N11.336 (2)C5—N11.338 (2)
C1—C21.392 (2)C5—H50.9300
C1—H10.9300C6—O11.231 (2)
C2—C31.390 (2)C6—N21.335 (2)
C2—C61.503 (2)N2—N31.418 (2)
C3—C41.386 (2)N2—H2N0.8830
C3—H30.9300N3—H3NA0.8746
C4—C51.381 (3)N3—H3NB0.8461
C4—H40.9300
N1—C1—C2123.70 (16)N1—C5—H5118.1
N1—C1—H1118.2C4—C5—H5118.1
C2—C1—H1118.2O1—C6—N2123.96 (16)
C3—C2—C1118.02 (16)O1—C6—C2120.55 (16)
C3—C2—C6124.35 (16)N2—C6—C2115.49 (15)
C1—C2—C6117.60 (15)C1—N1—C5117.04 (16)
C4—C3—C2118.93 (17)C6—N2—N3122.80 (15)
C4—C3—H3120.5C6—N2—H2N121.7
C2—C3—H3120.5N3—N2—H2N115.4
C5—C4—C3118.49 (17)N2—N3—H3NA111.0
C5—C4—H4120.8N2—N3—H3NB109.4
C3—C4—H4120.8H3NA—N3—H3NB99.3
N1—C5—C4123.81 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···N1i0.882.112.975 (2)166
N3—H3NA···O1ii0.872.223.045 (2)157
N3—H3NB···O1iii0.852.553.155 (2)130
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x+1/2, −y+3/2, −z+1; (iii) x−1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formulaC6H7N3O
Mr137.15
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)3.8855 (7), 10.5191 (5), 15.9058 (9)
V (Å3)650.10 (13)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.46 × 0.30 × 0.20
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		1534, 1051, 866
Rint0.015
(sin θ/λ)max (Å−1)0.681
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.087, 1.09
No. of reflections1051
No. of parameters92
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.18, −0.15

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), HELENA (Spek, 1996), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···N1i0.882.112.975 (2)166.4
N3—H3NA···O1ii0.872.223.045 (2)157.0
N3—H3NB···O1iii0.852.553.155 (2)129.5
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x+1/2, −y+3/2, −z+1; (iii) x−1/2, −y+3/2, −z+1.
Bond lengths and angles (Å, °) of nicotinohydrazide (I), picolinic acid hydrazide (II) and isonicotinohydrazide (III) top
(I)(II)(III)
N2—N31.418 (2)1.4221.429
C6—N21.335 (2)1.3341.346
C6—O11.231 (2)1.2351.235
C6—C21.503 (2)1.5071.513
N3—N2—C6122.80 (15)121.45121.06
N2—C6—O1123.96 (16)123.04122.07
N2—C6—C2115.49 (15)116.08115.90
O1—C6—C2120.55 (16)120.87122.00
N3—N2—C6—O10.17 (32)177.39175.13
C2—N2—C6—N3179.56 (19)177.72173.03
N2—C6—C2—C334.62 (27)177.06162.86
 

Acknowledgements

The authors thank the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), Fundação de Apoio à Pesquisa Científica e Tecnológica do Estado de Santa Catarina (FAPESC), Financiadora de Estudos e Projetos (FINEP) and Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES).

References

First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationBhat, T. N., Singh, T. P. & Vijayan, M. (1974). Acta Cryst. B30, 2921–2922.  CSD CrossRef CAS IUCr Journals Google Scholar
 First citationEnraf–Nonius (1994). CAD-4 EXPRESS. Version 5.1/1.2. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
 First citationJensen, L. H. (1954). J. Am. Chem. Soc. 76, 4663–4667.  CSD CrossRef CAS Web of Science Google Scholar
 First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationOuelleta, M., Aitkenb, S. M., Englishc, A. M. & Percivala, M. D. (2004). Arch. Biochem. Biophys. 431, 107–118.  Web of Science PubMed Google Scholar
 First citationPortalone, G. & Colapietro, M. (2008). Acta Cryst. E64, o304.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationSpek, A. L. (1996). HELENA. University of Utrecht, The Netherlands.  Google Scholar
 First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationZareef, M., Iqbla, R., Zaidi, J. H., Qadeer, G., Wong, W. Y. & Akhtar, H. (2006). Z. Kristallogr. New Cryst. Struct. 221, 307–308.  CAS Google Scholar
 First citationZhao, X., Yu, S. & Magliozzo, R. S. (2007). Biochemistry, 46, 3161–3170.  Web of Science CrossRef PubMed CAS Google Scholar

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ISSN: 2056-9890
Volume 64| Part 1| January 2008| Pages o302-o303
https://doi.org/10.1107/S160053680706655X
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