Nicotinohydrazide.

IN THE TITLE COMPOUND (ALTERNATIVE NAME: pyridine-3-carbo-hydrazide, C(6)H(7)N(3)O), the asymmetric unit contains a single mol-ecule. In contrast with nicotinic acid and nicotinamide, the C=O bond is found to be oriented cis with respect to the C(ipso) C N fragment in the pyridine ring. The pyridine ring and the hydrazide group make a dihedral angle of 34.0 (2)°. In the crystal structure, mol-ecules are associated into a three-dimensional framework by a combination of N-H⋯N and three-centre N-H⋯O hydrogen bonds.

Related literature

The structure of the same compound has been determined independently and is reported in the preceding paper (Priebe et al., 2008 ▶). For related literature, see: Bhat et al. (1974 ▶); Kutoglu & Scheringer (1983 ▶); Miwa et al. (1999 ▶); Portalone (2007 ▶); Portalone & Colapietro (2007 ▶). For computation of ring patterns formed by hydrogen bonds in crystal structures, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶); Motherwell et al. (1999 ▶).

Experimental

Crystal data

C6H7N3O

M = 137.15

Orthorhombic,

a = 3.8727 (10) Å

b = 10.481 (2) Å

c = 15.855 (2) Å

V = 643.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.15 × 0.05 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur S CCD diffractometer

Absorption correction: none

3076 measured reflections

1139 independent reflections

695 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.131

S = 1.19

1139 reflections

93 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807066561/bh2149sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066561/bh2149Isup2.hkl

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

C6H7N3O	F000 = 288
Mr = 137.15	Dx = 1.415 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71069 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6060 reflections
a = 3.8727 (10) Å	θ = 2.3–30.0º
b = 10.481 (2) Å	µ = 0.10 mm−1
c = 15.855 (2) Å	T = 298 (2) K
V = 643.6 (2) Å3	Plate, colourless
Z = 4	0.15 × 0.05 × 0.05 mm

Oxford Diffraction Xcalibur S CCD diffractometer	1139 independent reflections
Radiation source: Enhance (Mo) X-ray source	695 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
Detector resolution: 16.0696 pixels mm-1	θmax = 30.0º
T = 298(2) K	θmin = 2.3º
ω and φ scans	h = −5→5
Absorption correction: none	k = −14→14
3076 measured reflections	l = −22→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.022P)2 + 0.3733P] where P = (Fo2 + 2Fc2)/3
S = 1.19	(Δ/σ)max < 0.001
1139 reflections	Δρmax = 0.22 e Å−3
93 parameters	Δρmin = −0.22 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
O1	1.0228 (9)	0.1920 (2)	0.10123 (15)	0.0690 (8)
N1	0.4952 (10)	0.1249 (3)	0.32513 (17)	0.0622 (8)
N2	0.8838 (10)	0.4009 (3)	0.10818 (16)	0.0613 (9)
H21	0.777 (5)	0.464 (3)	0.1359 (12)	0.074*
N3	0.9984 (11)	0.4321 (3)	0.02617 (17)	0.0670 (9)
H31	1.210 (6)	0.4151 (6)	0.0228 (2)	0.080*
H32	0.889 (3)	0.3722 (18)	−0.0149 (13)	0.080*
C2	0.6160 (10)	0.1529 (3)	0.2485 (2)	0.0565 (9)
H2	0.5944	0.0902	0.2056	0.068*
C3	0.7709 (10)	0.2678 (3)	0.22785 (19)	0.0517 (8)
C4	0.7961 (10)	0.3597 (3)	0.2905 (2)	0.0574 (9)
H4	0.8954	0.4406	0.2786	0.069*
C5	0.6755 (12)	0.3321 (3)	0.3700 (2)	0.0648 (11)
H5	0.6931	0.3932	0.4140	0.078*
C6	0.5291 (13)	0.2149 (4)	0.3845 (2)	0.0673 (10)
H6	0.4474	0.1966	0.4397	0.081*
C7	0.9030 (11)	0.2833 (3)	0.14019 (19)	0.0545 (8)

	U11	U22	U33	U12	U13	U23
O1	0.089 (2)	0.0590 (14)	0.0593 (13)	0.0139 (16)	0.0077 (16)	−0.0061 (11)
N1	0.075 (2)	0.0528 (15)	0.0586 (15)	−0.0012 (19)	0.0015 (17)	0.0083 (13)
N2	0.083 (2)	0.0536 (15)	0.0468 (13)	0.0037 (17)	0.0062 (16)	0.0023 (12)
N3	0.083 (2)	0.0649 (17)	0.0526 (14)	−0.004 (2)	0.0038 (18)	0.0066 (13)
C2	0.071 (2)	0.0457 (15)	0.0528 (16)	0.0009 (18)	−0.0027 (18)	0.0009 (13)
C3	0.062 (2)	0.0440 (14)	0.0496 (15)	0.0019 (17)	−0.0038 (16)	−0.0007 (13)
C4	0.071 (2)	0.0475 (16)	0.0535 (16)	0.0034 (19)	−0.0040 (18)	−0.0040 (14)
C5	0.089 (3)	0.0574 (18)	0.0480 (16)	0.004 (2)	−0.004 (2)	−0.0041 (14)
C6	0.083 (3)	0.066 (2)	0.0526 (17)	0.005 (2)	0.002 (2)	0.0060 (16)
C7	0.063 (2)	0.0497 (15)	0.0505 (15)	0.0023 (18)	−0.0032 (17)	−0.0014 (14)

O1—C7	1.230 (4)	C2—H2	0.9500
N1—C2	1.334 (4)	C3—C4	1.387 (4)
N1—C6	1.340 (4)	C3—C7	1.490 (4)
N2—C7	1.335 (4)	C4—C5	1.375 (4)
N2—N3	1.412 (4)	C4—H4	0.9500
N2—H21	0.89 (4)	C5—C6	1.373 (5)
N3—H31	0.84 (5)	C5—H5	0.9500
N3—H32	1.00 (5)	C6—H6	0.9500
C2—C3	1.385 (4)
C2—N1—C6	116.8 (3)	C5—C4—C3	119.1 (3)
C7—N2—N3	123.1 (3)	C5—C4—H4	120.5
C7—N2—H21	121.2	C3—C4—H4	120.5
N3—N2—H21	115.4	C6—C5—C4	118.9 (3)
N2—N3—H31	108.4	C6—C5—H5	120.6
N2—N3—H32	108.7	C4—C5—H5	120.6
H31—N3—H32	103.9	N1—C6—C5	123.5 (3)
N1—C2—C3	124.0 (3)	N1—C6—H6	118.2
N1—C2—H2	118.0	C5—C6—H6	118.2
C3—C2—H2	118.0	O1—C7—N2	123.2 (3)
C2—C3—C4	117.7 (3)	O1—C7—C3	120.9 (3)
C2—C3—C7	117.6 (3)	N2—C7—C3	115.8 (3)
C4—C3—C7	124.6 (3)
C6—N1—C2—C3	0.0 (6)	C4—C5—C6—N1	−0.3 (7)
N1—C2—C3—C4	−1.1 (6)	N3—N2—C7—O1	0.2 (7)
N1—C2—C3—C7	178.1 (4)	N3—N2—C7—C3	179.8 (4)
C2—C3—C4—C5	1.5 (6)	C2—C3—C7—O1	−33.7 (6)
C7—C3—C4—C5	−177.6 (4)	C4—C3—C7—O1	145.5 (4)
C3—C4—C5—C6	−0.9 (6)	C2—C3—C7—N2	146.7 (4)
C2—N1—C6—C5	0.7 (7)	C4—C3—C7—N2	−34.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···N1i	0.89 (4)	2.09 (4)	2.964 (4)	168 (4)
N3—H31···O1ii	0.84 (5)	2.57 (5)	3.146 (4)	127 (4)
N3—H32···O1iii	1.00 (5)	2.08 (5)	3.027 (4)	157 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯N1i	0.89 (4)	2.09 (4)	2.964 (4)	168 (4)
N3—H31⋯O1ii	0.84 (5)	2.57 (5)	3.146 (4)	127 (4)
N3—H32⋯O1iii	1.00 (5)	2.08 (5)	3.027 (4)	157 (4)

Symmetry codes: (i) ; (ii) ; (iii) .