Nicotinohydrazide.

The title mol-ecule (alternative name: pyridine-3-carbohydrazide; C(6)H(7)N(3)O) 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 mol-ecule. 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 inter-molecular 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 ▶). The structures of picolinohydrazide (Zareef et al., 2006 ▶) and isonicotinohydrazide (Jensen, 1954 ▶; Bhat et al., 1974) have been published. For related literature on the 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

Crystal data

C6H7N3O

M = 137.15

Orthorhombic,

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)

R int = 0.015

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

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 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

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; 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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706655X/bh2145Isup2.hkl

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

C6H7N3O	F000 = 288
Mr = 137.15	Dx = 1.401 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 3.8855 (7) Å	θ = 5.5–18.7º
b = 10.5191 (5) Å	µ = 0.10 mm−1
c = 15.9058 (9) Å	T = 293 (2) K
V = 650.10 (13) Å3	Prismatic, colourless
Z = 4	0.46 × 0.30 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.015
Radiation source: fine-focus sealed tube	θmax = 29.0º
Monochromator: graphite	θmin = 2.3º
T = 293(2) K	h = −5→2
ω–2θ scans	k = −14→0
Absorption correction: none	l = −21→0
1534 measured reflections	3 standard reflections
1051 independent reflections	every 200 reflections
866 reflections with I > 2σ(I)	intensity decay: <1%

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031	w = 1/[σ2(Fo2) + (0.0344P)2 + 0.1144P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.087	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.18 e Å−3
1051 reflections	Δρmin = −0.15 e Å−3
92 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.040 (6)
Secondary atom site location: difference Fourier map

	x	y	z	Uiso*/Ueq
C1	0.3825 (5)	0.84759 (16)	0.25136 (11)	0.0373 (4)
H1	0.4007	0.9092	0.2930	0.045*
C2	0.2298 (5)	0.73203 (14)	0.27215 (10)	0.0319 (4)
C3	0.2025 (5)	0.64013 (16)	0.20969 (10)	0.0382 (4)
H3	0.1029	0.5617	0.2212	0.046*
C4	0.3262 (6)	0.66735 (19)	0.12995 (11)	0.0455 (5)
H4	0.3114	0.6076	0.0870	0.055*
C5	0.4720 (7)	0.78517 (19)	0.11576 (11)	0.0472 (5)
H5	0.5524	0.8032	0.0620	0.057*
C6	0.0965 (5)	0.71648 (17)	0.36028 (10)	0.0344 (4)
N1	0.5043 (5)	0.87491 (14)	0.17489 (10)	0.0440 (4)
N2	0.1167 (5)	0.59906 (15)	0.39179 (9)	0.0405 (4)
H2N	0.2155	0.5365	0.3637	0.049*
N3	−0.0001 (5)	0.56759 (16)	0.47365 (9)	0.0472 (4)
H3NA	0.0877	0.6189	0.5112	0.057*
H3NB	−0.2101	0.5876	0.4784	0.057*
O1	−0.0227 (5)	0.80795 (12)	0.39876 (8)	0.0487 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0405 (9)	0.0307 (7)	0.0405 (9)	0.0021 (8)	−0.0023 (8)	−0.0007 (6)
C2	0.0312 (8)	0.0314 (7)	0.0330 (7)	0.0041 (8)	−0.0025 (7)	−0.0001 (6)
C3	0.0445 (11)	0.0316 (8)	0.0384 (8)	0.0007 (8)	−0.0049 (8)	−0.0009 (7)
C4	0.0594 (14)	0.0442 (9)	0.0328 (8)	0.0060 (11)	−0.0039 (9)	−0.0057 (7)
C5	0.0550 (13)	0.0522 (10)	0.0345 (8)	0.0062 (11)	0.0050 (9)	0.0069 (8)
C6	0.0324 (9)	0.0367 (8)	0.0339 (7)	0.0012 (8)	−0.0035 (7)	−0.0040 (7)
N1	0.0481 (10)	0.0388 (7)	0.0451 (8)	0.0002 (8)	0.0019 (8)	0.0078 (6)
N2	0.0505 (10)	0.0373 (7)	0.0337 (7)	0.0027 (7)	0.0057 (7)	0.0007 (6)
N3	0.0557 (11)	0.0519 (9)	0.0338 (7)	−0.0021 (10)	0.0028 (8)	0.0045 (6)
O1	0.0604 (10)	0.0447 (7)	0.0409 (6)	0.0120 (7)	0.0060 (7)	−0.0060 (5)

C1—N1	1.336 (2)	C5—N1	1.338 (2)
C1—C2	1.392 (2)	C5—H5	0.9300
C1—H1	0.9300	C6—O1	1.231 (2)
C2—C3	1.390 (2)	C6—N2	1.335 (2)
C2—C6	1.503 (2)	N2—N3	1.418 (2)
C3—C4	1.386 (2)	N2—H2N	0.8830
C3—H3	0.9300	N3—H3NA	0.8746
C4—C5	1.381 (3)	N3—H3NB	0.8461
C4—H4	0.9300
N1—C1—C2	123.70 (16)	N1—C5—H5	118.1
N1—C1—H1	118.2	C4—C5—H5	118.1
C2—C1—H1	118.2	O1—C6—N2	123.96 (16)
C3—C2—C1	118.02 (16)	O1—C6—C2	120.55 (16)
C3—C2—C6	124.35 (16)	N2—C6—C2	115.49 (15)
C1—C2—C6	117.60 (15)	C1—N1—C5	117.04 (16)
C4—C3—C2	118.93 (17)	C6—N2—N3	122.80 (15)
C4—C3—H3	120.5	C6—N2—H2N	121.7
C2—C3—H3	120.5	N3—N2—H2N	115.4
C5—C4—C3	118.49 (17)	N2—N3—H3NA	111.0
C5—C4—H4	120.8	N2—N3—H3NB	109.4
C3—C4—H4	120.8	H3NA—N3—H3NB	99.3
N1—C5—C4	123.81 (17)

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

	(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
N3—N2—C6	122.80 (15)	121.45	121.06
N2—C6—O1	123.96 (16)	123.04	122.07
N2—C6—C2	115.49 (15)	116.08	115.90
O1—C6—C2	120.55 (16)	120.87	122.00
N3—N2—C6—O1	0.17 (32)	177.39	175.13
C2—N2—C6—N3	179.56 (19)	177.72	173.03
N2—C6—C2—C3	34.62 (27)	177.06	162.86

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) ; (ii) ; (iii) .

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