N'-Prop-ylisonicotinohydrazide.

In the title compound, C(9)H(11)N(3)O, the crystal structure is stabilized by a bifurcated inter-molecular N-H⋯(N,O) hydrogen bond and a C-H⋯O inter-action, leading to chains of mol-ecules.

Related literature

For background on the medicinal uses of isoniazid (isonicotinic acid hydrazide, INH) and INH hydrazide–hydrazones, see: Fox & Mitchison (1975 ▶); Kucukguzel et al. (2003 ▶). For the synthesis, see: Deng et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C9H11N3O

M = 177.21

Orthorhombic,

a = 13.010 (3) Å

b = 17.590 (4) Å

c = 8.0000 (16) Å

V = 1830.8 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 297 (2) K

0.43 × 0.28 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.963, T max = 0.981

9110 measured reflections

1634 independent reflections

986 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.145

S = 1.00

1634 reflections

125 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027955/hb2787sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027955/hb2787Isup2.hkl

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

C9H11N3O	F(000) = 752
Mr = 177.21	Dx = 1.286 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 1634 reflections
a = 13.010 (3) Å	θ = 2.0–25.1°
b = 17.590 (4) Å	µ = 0.09 mm−1
c = 8.0000 (16) Å	T = 297 K
V = 1830.8 (6) Å3	Block, yellow
Z = 8	0.43 × 0.28 × 0.22 mm

Bruker APEXII CCD diffractometer	1634 independent reflections
Radiation source: fine-focus sealed tube	986 reflections with I > 2σ(I)
graphite	Rint = 0.062
φ and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→15
Tmin = 0.963, Tmax = 0.981	k = −19→20
9110 measured reflections	l = −6→9

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: difmap (N-H) and geom (C-H)
wR(F2) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.070P)2 + 0.2547P] where P = (Fo2 + 2Fc2)/3
1634 reflections	(Δ/σ)max < 0.001
125 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.14 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.5785 (2)	0.3888 (2)	0.6946 (4)	0.0774 (9)
H1	0.5509	0.4037	0.7967	0.093*
C2	0.6065 (2)	0.44485 (16)	0.5836 (3)	0.0615 (7)
H2	0.5975	0.4959	0.6102	0.074*
C3	0.64780 (16)	0.42398 (14)	0.4339 (3)	0.0475 (6)
C4	0.65648 (19)	0.34815 (15)	0.4012 (3)	0.0599 (7)
H4	0.6825	0.3317	0.2992	0.072*
C5	0.6266 (2)	0.29651 (16)	0.5193 (4)	0.0699 (8)
H5	0.6338	0.2451	0.4945	0.084*
C6	0.67852 (18)	0.48038 (13)	0.3061 (3)	0.0493 (6)
C7	0.84373 (18)	0.63336 (14)	0.2827 (3)	0.0494 (6)
C8	0.8682 (2)	0.69467 (16)	0.1616 (4)	0.0771 (9)
H8A	0.8188	0.6941	0.0725	0.116*
H8B	0.9358	0.6866	0.1168	0.116*
H8C	0.8659	0.7430	0.2174	0.116*
C9	0.91433 (19)	0.62320 (16)	0.4257 (3)	0.0620 (8)
H9A	0.8751	0.6165	0.5263	0.093*
H9B	0.9573	0.6673	0.4365	0.093*
H9C	0.9565	0.5792	0.4073	0.093*
N1	0.58839 (18)	0.31505 (15)	0.6654 (3)	0.0767 (8)
N2	0.73950 (15)	0.53574 (12)	0.3610 (2)	0.0517 (6)
N3	0.76506 (16)	0.59328 (11)	0.2493 (2)	0.0544 (6)
O1	0.64977 (13)	0.47481 (10)	0.1615 (2)	0.0676 (6)
H2A	0.7650 (17)	0.5349 (14)	0.4690 (16)	0.072 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.092 (2)	0.087 (2)	0.0534 (18)	−0.0139 (18)	0.0222 (15)	0.0038 (16)
C2	0.0764 (18)	0.0595 (17)	0.0486 (16)	−0.0105 (14)	0.0130 (13)	0.0062 (13)
C3	0.0441 (14)	0.0593 (17)	0.0391 (13)	−0.0091 (11)	−0.0025 (11)	0.0023 (11)
C4	0.0596 (17)	0.0651 (19)	0.0552 (17)	−0.0069 (14)	0.0043 (12)	−0.0020 (14)
C5	0.0658 (18)	0.0616 (18)	0.082 (2)	−0.0076 (14)	−0.0046 (16)	0.0095 (16)
C6	0.0495 (14)	0.0609 (16)	0.0375 (14)	−0.0071 (12)	−0.0004 (11)	0.0039 (12)
C7	0.0465 (14)	0.0565 (16)	0.0453 (14)	−0.0012 (12)	0.0043 (11)	0.0032 (11)
C8	0.0697 (18)	0.078 (2)	0.084 (2)	−0.0169 (16)	0.0030 (16)	0.0294 (16)
C9	0.0562 (15)	0.0726 (18)	0.0574 (17)	−0.0112 (13)	−0.0062 (13)	0.0025 (13)
N1	0.0825 (17)	0.078 (2)	0.0697 (18)	−0.0147 (14)	0.0044 (13)	0.0211 (14)
N2	0.0602 (13)	0.0628 (14)	0.0321 (11)	−0.0156 (11)	−0.0034 (9)	0.0091 (10)
N3	0.0579 (13)	0.0647 (14)	0.0406 (12)	−0.0108 (11)	−0.0030 (9)	0.0147 (10)
O1	0.0759 (13)	0.0883 (14)	0.0387 (10)	−0.0241 (10)	−0.0097 (8)	0.0064 (9)

C1—N1	1.324 (4)	C6—N2	1.331 (3)
C1—C2	1.376 (4)	C7—N3	1.271 (3)
C1—H1	0.9300	C7—C8	1.484 (3)
C2—C3	1.363 (3)	C7—C9	1.478 (3)
C2—H2	0.9300	C8—H8A	0.9600
C3—C4	1.364 (3)	C8—H8B	0.9600
C3—C6	1.480 (3)	C8—H8C	0.9600
C4—C5	1.367 (4)	C9—H9A	0.9600
C4—H4	0.9300	C9—H9B	0.9600
C5—N1	1.312 (4)	C9—H9C	0.9600
C5—H5	0.9300	N2—N3	1.391 (2)
C6—O1	1.220 (3)	N2—H2A	0.926 (10)
N1—C1—C2	124.2 (3)	N3—C7—C9	126.6 (2)
N1—C1—H1	117.9	C8—C7—C9	117.4 (2)
C2—C1—H1	117.9	C7—C8—H8A	109.5
C3—C2—C1	118.6 (3)	C7—C8—H8B	109.5
C3—C2—H2	120.7	H8A—C8—H8B	109.5
C1—C2—H2	120.7	C7—C8—H8C	109.5
C4—C3—C2	117.7 (2)	H8A—C8—H8C	109.5
C4—C3—C6	120.0 (2)	H8B—C8—H8C	109.5
C2—C3—C6	122.2 (2)	C7—C9—H9A	109.5
C5—C4—C3	119.6 (3)	C7—C9—H9B	109.5
C5—C4—H4	120.2	H9A—C9—H9B	109.5
C3—C4—H4	120.2	C7—C9—H9C	109.5
N1—C5—C4	124.0 (3)	H9A—C9—H9C	109.5
N1—C5—H5	118.0	H9B—C9—H9C	109.5
C4—C5—H5	118.0	C5—N1—C1	116.0 (2)
O1—C6—N2	123.7 (2)	C6—N2—N3	117.57 (19)
O1—C6—C3	121.2 (2)	C6—N2—H2A	120.6 (15)
N2—C6—C3	115.1 (2)	N3—N2—H2A	121.8 (15)
N3—C7—C8	116.0 (2)	C7—N3—N2	117.42 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.93 (2)	2.17 (2)	3.001 (3)	149 (2)
N2—H2A···N3i	0.93 (2)	2.50 (2)	3.268 (2)	141.(2)
C9—H9A···N3i	0.96	2.58	3.525 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.926 (15)	2.172 (19)	3.001 (3)	149 (2)
N2—H2A⋯N3i	0.926 (15)	2.497 (16)	3.268 (2)	140.9 (19)
C9—H9A⋯N3i	0.96	2.58	3.525 (3)	167

Symmetry code: (i) .