2-(2-Nitro-phen-yl)acetohydrazide.

In the title compound, C8H9N3O3, the dihedral angle between the benzene ring and the acetohydrazide C-C(=O)-N-N plane [maximum deviation = 0.0471 (13) Å] is 87.62 (8)°. The nitro group is twisted by 19.3 (2)° with respect to the benzene ring. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into a double-column structure along the b axis.

Related literature

For the chemistry of hydrazides, ses: Domiano et al. (1984 ▶). For the biological properties of hydrazides, see: Kalsi et al. (2006 ▶); Masunari & Tavares (2007 ▶); Singh et al. (1992 ▶). For related structures, see: Ahmad et al. (2012 ▶); Dutkiewicz et al. (2009 ▶); Liu & Gao (2012 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H9N3O3

M = 195.18

Monoclinic,

a = 6.6962 (5) Å

b = 4.9388 (4) Å

c = 13.3593 (12) Å

β = 92.361 (8)°

V = 441.43 (6) Å3

Z = 2

Cu Kα radiation

μ = 0.98 mm−1

T = 173 K

0.36 × 0.28 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.667, T max = 0.925

3829 measured reflections

1967 independent reflections

1824 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.096

S = 1.05

1967 reflections

136 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 836 Friedel pairs

Flack parameter: 0.3 (3)

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED; 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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812047381/is5219sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047381/is5219Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047381/is5219Isup3.cml

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

C8H9N3O3	F(000) = 204
Mr = 195.18	Dx = 1.468 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 1694 reflections
a = 6.6962 (5) Å	θ = 3.3–32.5°
b = 4.9388 (4) Å	µ = 0.98 mm−1
c = 13.3593 (12) Å	T = 173 K
β = 92.361 (8)°	Chunk, colorless
V = 441.43 (6) Å3	0.36 × 0.28 × 0.08 mm
Z = 2

Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer	1967 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1824 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 16.0416 pixels mm-1	θmax = 89.1°, θmin = 7.3°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −6→6
Tmin = 0.667, Tmax = 0.925	l = −17→17
3829 measured reflections

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0517P)2 + 0.016P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1967 reflections	Δρmax = 0.19 e Å−3
136 parameters	Δρmin = −0.17 e Å−3
4 restraints	Absolute structure: Flack (1983), 836 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.3 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1	0.27090 (17)	0.8745 (2)	0.55928 (9)	0.0360 (3)
O2	0.0246 (2)	0.4300 (4)	0.71073 (10)	0.0632 (5)
O3	−0.0790 (2)	0.4790 (4)	0.85895 (11)	0.0576 (4)
N1	0.1751 (2)	0.4904 (3)	0.41437 (10)	0.0360 (3)
H1A	0.202 (3)	0.660 (4)	0.4013 (15)	0.043*
H1B	0.042 (2)	0.494 (5)	0.4186 (13)	0.043*
N2	0.2580 (2)	0.4374 (3)	0.51138 (10)	0.0318 (3)
H2	0.286 (3)	0.275 (4)	0.5269 (13)	0.038*
N3	0.0398 (2)	0.5265 (3)	0.79401 (10)	0.0358 (4)
C1	0.3052 (2)	0.6316 (3)	0.57676 (12)	0.0274 (3)
C2	0.4158 (2)	0.5384 (4)	0.67189 (12)	0.0338 (4)
H2A	0.3753	0.3547	0.6868	0.041*
H2B	0.5580	0.5363	0.6609	0.041*
C3	0.3777 (2)	0.7162 (3)	0.76100 (11)	0.0290 (3)
C4	0.2066 (2)	0.7141 (3)	0.81839 (11)	0.0293 (3)
C5	0.1834 (2)	0.8801 (4)	0.90089 (12)	0.0358 (4)
H5	0.0682	0.8696	0.9372	0.043*
C6	0.3327 (3)	1.0607 (4)	0.92857 (13)	0.0391 (4)
H6	0.3182	1.1750	0.9831	0.047*
C7	0.5050 (3)	1.0703 (4)	0.87408 (13)	0.0392 (4)
H7	0.6064	1.1916	0.8922	0.047*
C8	0.5260 (2)	0.9000 (4)	0.79295 (12)	0.0338 (4)
H8	0.6435	0.9080	0.7583	0.041*

	U11	U22	U33	U12	U13	U23
O1	0.0441 (6)	0.0188 (6)	0.0449 (7)	0.0021 (5)	−0.0010 (5)	0.0046 (5)
O2	0.0697 (9)	0.0736 (12)	0.0466 (8)	−0.0375 (9)	0.0085 (6)	−0.0133 (8)
O3	0.0440 (7)	0.0653 (11)	0.0651 (9)	−0.0193 (7)	0.0216 (6)	−0.0069 (8)
N1	0.0431 (7)	0.0306 (8)	0.0346 (7)	−0.0004 (7)	0.0062 (6)	0.0013 (6)
N2	0.0423 (7)	0.0197 (7)	0.0337 (7)	0.0046 (6)	0.0070 (5)	0.0036 (6)
N3	0.0339 (7)	0.0332 (9)	0.0405 (8)	−0.0061 (6)	0.0037 (6)	0.0013 (6)
C1	0.0296 (7)	0.0197 (8)	0.0336 (8)	0.0031 (6)	0.0087 (6)	0.0028 (6)
C2	0.0387 (8)	0.0261 (9)	0.0369 (9)	0.0096 (7)	0.0048 (6)	0.0034 (7)
C3	0.0314 (7)	0.0254 (8)	0.0303 (7)	0.0034 (6)	0.0006 (6)	0.0079 (7)
C4	0.0288 (7)	0.0242 (8)	0.0347 (8)	−0.0011 (6)	0.0007 (6)	0.0043 (7)
C5	0.0385 (8)	0.0353 (10)	0.0338 (8)	−0.0005 (8)	0.0048 (6)	0.0011 (7)
C6	0.0509 (10)	0.0333 (10)	0.0330 (9)	−0.0026 (8)	−0.0003 (7)	−0.0012 (7)
C7	0.0432 (9)	0.0332 (10)	0.0404 (9)	−0.0089 (8)	−0.0076 (7)	0.0077 (8)
C8	0.0300 (7)	0.0351 (10)	0.0362 (8)	−0.0023 (7)	0.0003 (6)	0.0095 (7)

O1—C1	1.242 (2)	C2—H2B	0.9700
O2—N3	1.2107 (19)	C3—C8	1.399 (2)
O3—N3	1.2236 (18)	C3—C4	1.405 (2)
N1—N2	1.413 (2)	C4—C5	1.387 (2)
N1—H1A	0.877 (16)	C5—C6	1.379 (3)
N1—H1B	0.898 (14)	C5—H5	0.9300
N2—C1	1.327 (2)	C6—C7	1.390 (3)
N2—H2	0.845 (16)	C6—H6	0.9300
N3—C4	1.477 (2)	C7—C8	1.384 (3)
C1—C2	1.516 (2)	C7—H7	0.9300
C2—C3	1.509 (2)	C8—H8	0.9300
C2—H2A	0.9700
N2—N1—H1A	106.5 (14)	C8—C3—C4	115.04 (15)
N2—N1—H1B	107.5 (12)	C8—C3—C2	118.50 (14)
H1A—N1—H1B	102 (2)	C4—C3—C2	126.45 (15)
C1—N2—N1	122.93 (15)	C5—C4—C3	123.33 (15)
C1—N2—H2	118.6 (13)	C5—C4—N3	115.94 (13)
N1—N2—H2	118.3 (13)	C3—C4—N3	120.72 (14)
O2—N3—O3	122.93 (16)	C6—C5—C4	119.47 (15)
O2—N3—C4	118.92 (13)	C6—C5—H5	120.3
O3—N3—C4	118.13 (14)	C4—C5—H5	120.3
O1—C1—N2	122.50 (16)	C5—C6—C7	119.32 (16)
O1—C1—C2	122.07 (16)	C5—C6—H6	120.3
N2—C1—C2	115.32 (15)	C7—C6—H6	120.3
C3—C2—C1	113.10 (14)	C8—C7—C6	120.18 (17)
C3—C2—H2A	109.0	C8—C7—H7	119.9
C1—C2—H2A	109.0	C6—C7—H7	119.9
C3—C2—H2B	109.0	C7—C8—C3	122.65 (15)
C1—C2—H2B	109.0	C7—C8—H8	118.7
H2A—C2—H2B	107.8	C3—C8—H8	118.7
N1—N2—C1—O1	3.6 (2)	O3—N3—C4—C5	−18.1 (2)
N1—N2—C1—C2	−172.72 (13)	O2—N3—C4—C3	−20.3 (2)
O1—C1—C2—C3	32.4 (2)	O3—N3—C4—C3	160.87 (17)
N2—C1—C2—C3	−151.21 (14)	C3—C4—C5—C6	1.0 (2)
C1—C2—C3—C8	−103.44 (17)	N3—C4—C5—C6	179.95 (15)
C1—C2—C3—C4	77.9 (2)	C4—C5—C6—C7	−0.9 (3)
C8—C3—C4—C5	0.0 (2)	C5—C6—C7—C8	0.0 (3)
C2—C3—C4—C5	178.63 (16)	C6—C7—C8—C3	1.0 (3)
C8—C3—C4—N3	−178.96 (14)	C4—C3—C8—C7	−1.0 (2)
C2—C3—C4—N3	−0.3 (2)	C2—C3—C8—C7	−179.73 (16)
O2—N3—C4—C5	160.74 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1i	0.90 (1)	2.21 (2)	3.0752 (19)	163 (2)
N2—H2···O1ii	0.85 (2)	2.03 (2)	2.8531 (18)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1i	0.90 (1)	2.21 (2)	3.0752 (19)	163 (2)
N2—H2⋯O1ii	0.85 (2)	2.03 (2)	2.8531 (18)	165 (2)

Symmetry codes: (i) ; (ii) .