2-(4-Methyl-anilino)acetohydrazide.

In the title mol-ecule, C(9)H(13)N(3)O, the non-hydrogen atoms of the hydrazide group are essentially planar [maximum deviation = 0.028 (1) Å for one of the N atoms]. The mean plane of this group forms a dihedral angle of 83.34 (5)° with the plane of the benzene ring. In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯O, N-H⋯N and weak C-H⋯N hydrogen bonds into a two-dimensional network parallel to the ab plane. Additional stabilization is provided by a weak C-H⋯π inter-action.

Related literature

For the biological activity of hydrazide derivatives, see: Ozdemir et al. (2009 ▶); Khattab (2005 ▶). For synthetic applications, see: Isloor et al. (2009 ▶); Holla & Udupa (1992 ▶). For a related structure, see: Zhang & Shi (2009 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C9H13N3O

M = 179.22

Triclinic,

a = 5.1481 (1) Å

b = 5.9262 (2) Å

c = 15.4756 (4) Å

α = 87.002 (2)°

β = 84.282 (2)°

γ = 82.849 (2)°

V = 465.76 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.52 × 0.15 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.956, T max = 0.994

11697 measured reflections

2703 independent reflections

2301 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.110

S = 1.03

2703 reflections

170 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033169/lh2884sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033169/lh2884Isup2.hkl

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

C9H13N3O	Z = 2
Mr = 179.22	F(000) = 192
Triclinic, P1	Dx = 1.278 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.1481 (1) Å	Cell parameters from 6230 reflections
b = 5.9262 (2) Å	θ = 2.7–31.2°
c = 15.4756 (4) Å	µ = 0.09 mm−1
α = 87.002 (2)°	T = 100 K
β = 84.282 (2)°	Block, colourless
γ = 82.849 (2)°	0.52 × 0.15 × 0.07 mm
V = 465.76 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	2703 independent reflections
Radiation source: fine-focus sealed tube	2301 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 30.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
Tmin = 0.956, Tmax = 0.994	k = −8→8
11697 measured reflections	l = −21→21

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0559P)2 + 0.1344P] where P = (Fo2 + 2Fc2)/3
2703 reflections	(Δ/σ)max < 0.001
170 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	0.63005 (14)	0.15409 (11)	0.39934 (5)	0.01915 (17)
N1	0.43188 (17)	0.74133 (14)	0.33320 (6)	0.01783 (18)
N2	0.26039 (16)	0.39523 (13)	0.43209 (5)	0.01650 (18)
N3	0.12716 (17)	0.23345 (14)	0.48445 (6)	0.01765 (18)
C1	0.1124 (2)	0.95874 (17)	0.24809 (7)	0.0231 (2)
C2	−0.0573 (2)	0.9751 (2)	0.18340 (8)	0.0282 (2)
C3	−0.0748 (2)	0.7920 (2)	0.13190 (7)	0.0280 (2)
C4	0.0857 (2)	0.5915 (2)	0.14806 (7)	0.0257 (2)
C5	0.2577 (2)	0.57064 (17)	0.21309 (7)	0.0208 (2)
C6	0.27314 (19)	0.75502 (16)	0.26432 (6)	0.01770 (19)
C7	0.62171 (19)	0.54434 (16)	0.34553 (7)	0.01795 (19)
C8	0.50373 (18)	0.34635 (15)	0.39460 (6)	0.01517 (18)
C9	−0.2624 (3)	0.8132 (3)	0.06212 (9)	0.0405 (3)
H1A	0.116 (3)	1.091 (3)	0.2848 (10)	0.031 (4)*
H2A	−0.167 (3)	1.117 (3)	0.1751 (11)	0.042 (4)*
H4A	0.081 (3)	0.457 (3)	0.1131 (10)	0.032 (4)*
H5A	0.363 (3)	0.424 (3)	0.2235 (10)	0.031 (4)*
H7A	0.713 (3)	0.484 (2)	0.2916 (9)	0.024 (3)*
H7B	0.757 (3)	0.592 (2)	0.3797 (9)	0.026 (3)*
H9A	−0.199 (4)	0.895 (4)	0.0098 (14)	0.070 (6)*
H9B	−0.435 (4)	0.878 (3)	0.0840 (13)	0.064 (6)*
H9C	−0.290 (4)	0.655 (4)	0.0400 (14)	0.072 (6)*
H1N1	0.485 (3)	0.869 (3)	0.3461 (9)	0.029 (4)*
H1N2	0.185 (3)	0.538 (3)	0.4343 (9)	0.028 (3)*
H1N3	0.250 (3)	0.125 (2)	0.5030 (9)	0.023 (3)*
H2N3	0.031 (3)	0.167 (2)	0.4485 (9)	0.028 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0173 (3)	0.0139 (3)	0.0257 (4)	0.0010 (2)	−0.0024 (3)	−0.0012 (3)
N1	0.0208 (4)	0.0112 (3)	0.0219 (4)	−0.0032 (3)	−0.0028 (3)	−0.0005 (3)
N2	0.0155 (4)	0.0110 (3)	0.0223 (4)	−0.0013 (3)	0.0001 (3)	0.0014 (3)
N3	0.0159 (4)	0.0135 (4)	0.0233 (4)	−0.0029 (3)	−0.0015 (3)	0.0035 (3)
C1	0.0247 (5)	0.0183 (5)	0.0246 (5)	0.0002 (4)	0.0004 (4)	0.0021 (4)
C2	0.0246 (5)	0.0294 (6)	0.0277 (6)	0.0031 (4)	−0.0008 (4)	0.0081 (4)
C3	0.0224 (5)	0.0410 (6)	0.0209 (5)	−0.0083 (4)	−0.0023 (4)	0.0072 (4)
C4	0.0274 (5)	0.0303 (5)	0.0210 (5)	−0.0109 (4)	−0.0013 (4)	−0.0011 (4)
C5	0.0225 (5)	0.0183 (4)	0.0216 (5)	−0.0041 (3)	−0.0006 (4)	−0.0007 (3)
C6	0.0178 (4)	0.0160 (4)	0.0189 (4)	−0.0033 (3)	0.0006 (3)	0.0015 (3)
C7	0.0156 (4)	0.0158 (4)	0.0222 (5)	−0.0027 (3)	−0.0004 (3)	0.0010 (3)
C8	0.0156 (4)	0.0140 (4)	0.0165 (4)	−0.0020 (3)	−0.0032 (3)	−0.0019 (3)
C9	0.0291 (7)	0.0679 (10)	0.0258 (6)	−0.0130 (6)	−0.0079 (5)	0.0127 (6)

O1—C8	1.2421 (11)	C2—H2A	0.962 (17)
N1—C6	1.3995 (13)	C3—C4	1.3867 (17)
N1—C7	1.4437 (12)	C3—C9	1.5094 (17)
N1—H1N1	0.876 (15)	C4—C5	1.3961 (15)
N2—C8	1.3313 (12)	C4—H4A	0.988 (15)
N2—N3	1.4205 (11)	C5—C6	1.3978 (14)
N2—H1N2	0.886 (15)	C5—H5A	0.979 (15)
N3—H1N3	0.902 (14)	C7—C8	1.5213 (13)
N3—H2N3	0.912 (15)	C7—H7A	0.978 (14)
C1—C2	1.3850 (16)	C7—H7B	0.989 (14)
C1—C6	1.4022 (13)	C9—H9A	0.97 (2)
C1—H1A	0.993 (15)	C9—H9B	0.96 (2)
C2—C3	1.3963 (18)	C9—H9C	1.04 (2)
C6—N1—C7	120.37 (8)	C4—C5—C6	120.25 (10)
C6—N1—H1N1	115.9 (10)	C4—C5—H5A	119.3 (9)
C7—N1—H1N1	113.7 (10)	C6—C5—H5A	120.4 (9)
C8—N2—N3	122.60 (8)	C5—C6—N1	122.90 (9)
C8—N2—H1N2	120.9 (10)	C5—C6—C1	118.06 (10)
N3—N2—H1N2	115.5 (10)	N1—C6—C1	118.97 (9)
N2—N3—H1N3	107.5 (9)	N1—C7—C8	113.36 (8)
N2—N3—H2N3	106.4 (9)	N1—C7—H7A	114.3 (8)
H1N3—N3—H2N3	107.4 (12)	C8—C7—H7A	106.5 (8)
C2—C1—C6	120.65 (10)	N1—C7—H7B	107.1 (8)
C2—C1—H1A	119.7 (9)	C8—C7—H7B	108.4 (8)
C6—C1—H1A	119.6 (9)	H7A—C7—H7B	107.0 (12)
C1—C2—C3	121.82 (10)	O1—C8—N2	123.22 (9)
C1—C2—H2A	118.2 (10)	O1—C8—C7	121.37 (9)
C3—C2—H2A	120.0 (10)	N2—C8—C7	115.40 (8)
C4—C3—C2	117.19 (10)	C3—C9—H9A	113.1 (13)
C4—C3—C9	121.88 (12)	C3—C9—H9B	111.3 (12)
C2—C3—C9	120.92 (12)	H9A—C9—H9B	111.5 (17)
C3—C4—C5	122.03 (10)	C3—C9—H9C	112.3 (12)
C3—C4—H4A	120.2 (9)	H9A—C9—H9C	103.7 (17)
C5—C4—H4A	117.8 (9)	H9B—C9—H9C	104.4 (17)
C6—C1—C2—C3	−0.26 (17)	C7—N1—C6—C1	−172.79 (9)
C1—C2—C3—C4	−0.06 (17)	C2—C1—C6—C5	0.35 (15)
C1—C2—C3—C9	179.61 (11)	C2—C1—C6—N1	−176.67 (9)
C2—C3—C4—C5	0.28 (16)	C6—N1—C7—C8	−83.08 (11)
C9—C3—C4—C5	−179.38 (11)	N3—N2—C8—O1	2.92 (14)
C3—C4—C5—C6	−0.19 (16)	N3—N2—C8—C7	−176.34 (8)
C4—C5—C6—N1	176.77 (9)	N1—C7—C8—O1	169.09 (8)
C4—C5—C6—C1	−0.13 (15)	N1—C7—C8—N2	−11.63 (12)
C7—N1—C6—C5	10.34 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.875 (17)	2.162 (17)	3.0271 (11)	170.0 (13)
N2—H1N2···N3ii	0.887 (17)	2.287 (16)	3.0302 (12)	141.3 (13)
N3—H1N3···O1iii	0.901 (14)	2.252 (13)	3.0614 (11)	149.4 (13)
N3—H2N3···O1iv	0.914 (14)	2.281 (15)	3.0889 (12)	147.1 (12)
C7—H7B···N3v	0.991 (15)	2.545 (14)	3.4341 (14)	149.2 (11)
C9—H9B···Cgiv	0.96 (2)	2.94 (2)	3.7469 (16)	142.3 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.875 (17)	2.162 (17)	3.0271 (11)	170.0 (13)
N2—H1N2⋯N3ii	0.887 (17)	2.287 (16)	3.0302 (12)	141.3 (13)
N3—H1N3⋯O1iii	0.901 (14)	2.252 (13)	3.0614 (11)	149.4 (13)
N3—H2N3⋯O1iv	0.914 (14)	2.281 (15)	3.0889 (12)	147.1 (12)
C7—H7B⋯N3v	0.991 (15)	2.545 (14)	3.4341 (14)	149.2 (11)
C9—H9B⋯Cgiv	0.96 (2)	2.94 (2)	3.7469 (16)	142.3 (14)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg is the centroid of the C1–C6 benzene ring.