2-(4-Methyl-phen-yl)acetohydrazide.

In the title compound, C9H12N2O, the dihedral angle between the benzene ring and the mean plane of the acetohydrazide group is 88.2 (7)°. In the crystal, N-H⋯O hydrogen bonds and weak C-H⋯O inter-actions link the mol-ecules into infinite ribbons along [001].

Related literature

For hydrazides as precursors in the synthesis of heterocyclic systems, see: Narayana et al. (2005 ▶). For related structures, see: Hanif et al. (2007 ▶); Liu & Gao (2012 ▶); Fun et al. (2011 ▶). For standard bond lengths, see: Allen et al. (1987) ▶.

Experimental

Crystal data

C9H12N2O

M = 164.21

Monoclinic,

a = 15.4261 (16) Å

b = 6.2618 (7) Å

c = 9.2073 (10) Å

β = 106.651 (12)°

V = 852.09 (16) Å3

Z = 4

Cu Kα radiation

μ = 0.69 mm−1

T = 173 K

0.32 × 0.22 × 0.08 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012 ▶) T min = 0.746, T max = 1.000

4845 measured reflections

1675 independent reflections

1359 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.151

S = 1.07

1675 reflections

119 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); 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/S160053681204799X/ng5307sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204799X/ng5307Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204799X/ng5307Isup3.cml

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

C9H12N2O	F(000) = 352
Mr = 164.21	Dx = 1.280 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 1566 reflections
a = 15.4261 (16) Å	θ = 3.0–72.3°
b = 6.2618 (7) Å	µ = 0.69 mm−1
c = 9.2073 (10) Å	T = 173 K
β = 106.651 (12)°	Chunk, colorless
V = 852.09 (16) Å3	0.32 × 0.22 × 0.08 mm
Z = 4

Agilent Xcalibur (Eos, Gemini) diffractometer	1675 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1359 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 16.0416 pixels mm-1	θmax = 72.5°, θmin = 3.0°
ω scans	h = −18→19
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012)	k = −7→4
Tmin = 0.746, Tmax = 1.000	l = −10→11
4845 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0882P)2 + 0.1271P] where P = (Fo2 + 2Fc2)/3
1675 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.26 e Å−3
3 restraints	Δρmin = −0.21 e Å−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	0.08543 (9)	0.1283 (2)	0.28834 (14)	0.0417 (4)
N1	−0.06203 (11)	0.2284 (3)	0.0460 (2)	0.0396 (4)
H1A	−0.0731 (15)	0.323 (3)	0.110 (2)	0.048*
H1B	−0.0656 (15)	0.105 (3)	0.093 (2)	0.048*
N2	0.03002 (10)	0.2537 (2)	0.05112 (18)	0.0336 (4)
H2	0.0399 (15)	0.293 (3)	−0.030 (2)	0.040*
C1	0.09783 (12)	0.1991 (3)	0.17011 (19)	0.0319 (4)
C2	0.19169 (12)	0.2268 (3)	0.1528 (2)	0.0370 (4)
H2A	0.1873	0.2917	0.0553	0.044*
H2B	0.2199	0.0878	0.1551	0.044*
C3	0.25012 (11)	0.3654 (3)	0.27779 (19)	0.0340 (4)
C4	0.22379 (12)	0.5730 (3)	0.2991 (2)	0.0381 (4)
H4	0.1707	0.6279	0.2343	0.046*
C5	0.27565 (12)	0.6990 (3)	0.4157 (2)	0.0394 (4)
H5	0.2562	0.8363	0.4292	0.047*
C6	0.35650 (12)	0.6232 (3)	0.5132 (2)	0.0381 (4)
C7	0.38281 (12)	0.4170 (3)	0.4904 (2)	0.0402 (5)
H7	0.4366	0.3630	0.5538	0.048*
C8	0.33043 (12)	0.2894 (3)	0.3747 (2)	0.0373 (4)
H8	0.3495	0.1515	0.3621	0.045*
C9	0.41413 (15)	0.7621 (4)	0.6381 (2)	0.0518 (6)
H9A	0.3783	0.8125	0.7009	0.078*
H9B	0.4365	0.8817	0.5944	0.078*
H9C	0.4642	0.6802	0.6985	0.078*

	U11	U22	U33	U12	U13	U23
O1	0.0437 (8)	0.0512 (8)	0.0323 (7)	−0.0037 (6)	0.0144 (6)	0.0019 (5)
N1	0.0299 (8)	0.0442 (9)	0.0452 (10)	−0.0016 (6)	0.0115 (7)	−0.0051 (7)
N2	0.0311 (8)	0.0391 (8)	0.0321 (8)	−0.0006 (6)	0.0113 (6)	0.0010 (6)
C1	0.0347 (9)	0.0320 (8)	0.0298 (9)	−0.0025 (6)	0.0105 (7)	−0.0047 (6)
C2	0.0328 (9)	0.0492 (10)	0.0307 (9)	−0.0012 (7)	0.0119 (7)	−0.0038 (7)
C3	0.0293 (8)	0.0435 (10)	0.0310 (9)	−0.0022 (7)	0.0113 (7)	0.0004 (7)
C4	0.0288 (9)	0.0460 (10)	0.0392 (10)	0.0037 (7)	0.0095 (7)	0.0048 (7)
C5	0.0327 (9)	0.0409 (10)	0.0468 (11)	−0.0015 (7)	0.0151 (8)	−0.0014 (8)
C6	0.0303 (9)	0.0484 (10)	0.0374 (10)	−0.0060 (7)	0.0126 (7)	−0.0032 (8)
C7	0.0301 (9)	0.0496 (11)	0.0388 (10)	0.0012 (7)	0.0065 (7)	0.0040 (8)
C8	0.0340 (9)	0.0386 (9)	0.0398 (10)	0.0027 (7)	0.0115 (8)	0.0021 (7)
C9	0.0403 (11)	0.0650 (14)	0.0498 (12)	−0.0083 (9)	0.0121 (10)	−0.0157 (10)

O1—C1	1.240 (2)	C4—C5	1.387 (3)
N1—N2	1.416 (2)	C4—H4	0.9300
N1—H1A	0.889 (16)	C5—C6	1.395 (3)
N1—H1B	0.898 (15)	C5—H5	0.9300
N2—C1	1.325 (2)	C6—C7	1.388 (3)
N2—H2	0.842 (15)	C6—C9	1.511 (3)
C1—C2	1.511 (2)	C7—C8	1.390 (3)
C2—C3	1.515 (2)	C7—H7	0.9300
C2—H2A	0.9700	C8—H8	0.9300
C2—H2B	0.9700	C9—H9A	0.9600
C3—C8	1.387 (2)	C9—H9B	0.9600
C3—C4	1.393 (3)	C9—H9C	0.9600
N2—N1—H1A	106.6 (15)	C3—C4—H4	119.5
N2—N1—H1B	106.3 (15)	C4—C5—C6	121.05 (17)
H1A—N1—H1B	102 (2)	C4—C5—H5	119.5
C1—N2—N1	123.05 (15)	C6—C5—H5	119.5
C1—N2—H2	120.6 (15)	C7—C6—C5	117.77 (17)
N1—N2—H2	116.0 (15)	C7—C6—C9	121.12 (17)
O1—C1—N2	122.32 (16)	C5—C6—C9	121.11 (18)
O1—C1—C2	121.82 (16)	C6—C7—C8	121.30 (16)
N2—C1—C2	115.86 (15)	C6—C7—H7	119.3
C1—C2—C3	111.39 (14)	C8—C7—H7	119.3
C1—C2—H2A	109.3	C3—C8—C7	120.79 (17)
C3—C2—H2A	109.3	C3—C8—H8	119.6
C1—C2—H2B	109.3	C7—C8—H8	119.6
C3—C2—H2B	109.3	C6—C9—H9A	109.5
H2A—C2—H2B	108.0	C6—C9—H9B	109.5
C8—C3—C4	118.18 (16)	H9A—C9—H9B	109.5
C8—C3—C2	121.29 (16)	C6—C9—H9C	109.5
C4—C3—C2	120.52 (15)	H9A—C9—H9C	109.5
C5—C4—C3	120.90 (16)	H9B—C9—H9C	109.5
C5—C4—H4	119.5
N1—N2—C1—O1	−2.6 (3)	C3—C4—C5—C6	1.2 (3)
N1—N2—C1—C2	177.00 (15)	C4—C5—C6—C7	−0.6 (3)
O1—C1—C2—C3	−55.6 (2)	C4—C5—C6—C9	178.63 (17)
N2—C1—C2—C3	124.79 (16)	C5—C6—C7—C8	−0.1 (3)
C1—C2—C3—C8	120.96 (18)	C9—C6—C7—C8	−179.37 (18)
C1—C2—C3—C4	−58.4 (2)	C4—C3—C8—C7	0.4 (3)
C8—C3—C4—C5	−1.1 (3)	C2—C3—C8—C7	−179.03 (16)
C2—C3—C4—C5	178.30 (16)	C6—C7—C8—C3	0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.84 (2)	2.05 (2)	2.884 (2)	171 (2)
C2—H2A···O1i	0.97	2.56	3.408 (2)	146
N1—H1A···O1ii	0.89 (2)	2.16 (2)	3.007 (2)	159 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.84 (2)	2.05 (2)	2.884 (2)	171 (2)
C2—H2A⋯O1i	0.97	2.56	3.408 (2)	146
N1—H1A⋯O1ii	0.89 (2)	2.16 (2)	3.007 (2)	159 (2)

Symmetry codes: (i) ; (ii) .