4-Methoxy-benzohydrazide.

The title compound, C(8)H(10)N(2)O(2), is stabilized by three inter-molecular hydrogen bonds of the N-H⋯O and N-H⋯N types. Two intra-molecular inter-actions of the N-H⋯O and C-H⋯O types are also observed.

Related literature

For related structures see: Ashiq, Jamal et al. (2008 ▶); Jamal et al. (2008 ▶), Kallel et al. (1992 ▶); Saraogi et al. (2002 ▶); For the biological activity of hydrazides, see: Ara et al. (2007 ▶); Ashiq, Ara et al. (2008 ▶); El-Emam et al. (2004 ▶); Maqsood et al. (2006 ▶).

Experimental

Crystal data

C8H10N2O2

M = 166.18

Orthorhombic,

a = 3.9887 (1) Å

b = 6.1487 (2) Å

c = 32.8919 (9) Å

V = 806.68 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.22 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.979, T max = 0.992

17597 measured reflections

1288 independent reflections

1052 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.147

S = 1.03

1288 reflections

119 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021345/pv2163sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021345/pv2163Isup2.hkl

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

C8H10N2O2	F(000) = 352
Mr = 166.18	Dx = 1.368 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1288 reflections
a = 3.9887 (1) Å	θ = 1.2–28.7°
b = 6.1487 (2) Å	µ = 0.10 mm−1
c = 32.8919 (9) Å	T = 296 K
V = 806.68 (4) Å3	Needle, colourless
Z = 4	0.22 × 0.12 × 0.10 mm

Bruker Kappa APEXII CCD diffractometer	1288 independent reflections
Radiation source: fine-focus sealed tube	1052 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 7.40 pixels mm-1	θmax = 28.7°, θmin = 1.2°
ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→8
Tmin = 0.979, Tmax = 0.992	l = −44→44
17597 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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.1097P)2 + 0.027P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1288 reflections	Δρmax = 0.39 e Å−3
119 parameters	Δρmin = −0.24 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.058 (15)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.9709 (4)	1.2503 (3)	0.05610 (4)	0.0459 (5)
O2	0.2810 (5)	0.8530 (3)	0.21180 (5)	0.0600 (6)
N1	0.8024 (5)	0.9374 (3)	0.02782 (5)	0.0384 (5)
N2	0.9644 (5)	0.9802 (3)	−0.00972 (5)	0.0376 (5)
C1	0.8272 (5)	1.0744 (3)	0.05921 (5)	0.0320 (5)
C2	0.6754 (5)	1.0039 (3)	0.09850 (5)	0.0325 (5)
C3	0.5396 (7)	0.8001 (4)	0.10519 (6)	0.0427 (6)
C4	0.4053 (6)	0.7433 (4)	0.14251 (6)	0.0436 (7)
C5	0.4061 (6)	0.8925 (4)	0.17369 (6)	0.0415 (6)
C6	0.5410 (8)	1.0960 (4)	0.16743 (6)	0.0505 (8)
C7	0.6748 (6)	1.1507 (4)	0.13034 (7)	0.0441 (7)
C8	0.1357 (9)	0.6492 (5)	0.21996 (8)	0.0627 (10)
H1	0.694 (10)	0.822 (6)	0.0282 (9)	0.0752*
H2A	1.157 (12)	1.055 (6)	−0.0037 (11)	0.0940*
H2B	0.832 (12)	1.068 (6)	−0.0262 (10)	0.0940*
H3	0.53858	0.69896	0.08416	0.0513*
H4	0.31513	0.60542	0.14648	0.0523*
H6	0.54148	1.19702	0.18846	0.0606*
H7	0.76633	1.28832	0.12659	0.0529*
H8A	0.05128	0.64745	0.24729	0.0940*
H8B	0.30181	0.53746	0.21686	0.0940*
H8C	−0.04508	0.62368	0.20129	0.0940*

	U11	U22	U33	U12	U13	U23
O1	0.0595 (10)	0.0336 (8)	0.0445 (8)	−0.0109 (8)	0.0000 (7)	0.0023 (7)
O2	0.0770 (12)	0.0652 (12)	0.0379 (9)	0.0043 (11)	0.0195 (8)	0.0041 (8)
N1	0.0521 (10)	0.0313 (9)	0.0317 (8)	−0.0065 (9)	0.0048 (7)	0.0016 (7)
N2	0.0451 (9)	0.0348 (10)	0.0329 (8)	0.0030 (8)	0.0062 (7)	0.0040 (7)
C1	0.0350 (9)	0.0285 (9)	0.0325 (9)	0.0020 (8)	−0.0038 (7)	0.0031 (8)
C2	0.0352 (9)	0.0317 (9)	0.0306 (9)	0.0028 (8)	−0.0027 (7)	0.0018 (8)
C3	0.0593 (12)	0.0363 (11)	0.0326 (9)	−0.0064 (11)	0.0021 (10)	−0.0029 (8)
C4	0.0544 (12)	0.0384 (12)	0.0379 (10)	−0.0068 (11)	0.0031 (9)	0.0044 (9)
C5	0.0457 (10)	0.0469 (13)	0.0318 (10)	0.0076 (10)	0.0033 (8)	0.0031 (9)
C6	0.0708 (16)	0.0418 (13)	0.0390 (11)	0.0024 (13)	0.0038 (11)	−0.0096 (10)
C7	0.0566 (12)	0.0318 (11)	0.0438 (11)	−0.0025 (11)	0.0022 (11)	−0.0023 (9)
C8	0.0665 (16)	0.0722 (19)	0.0493 (14)	0.0039 (17)	0.0159 (12)	0.0163 (13)

O1—C1	1.228 (3)	C3—C4	1.384 (3)
O2—C5	1.371 (3)	C4—C5	1.376 (3)
O2—C8	1.407 (4)	C5—C6	1.378 (4)
N1—N2	1.418 (2)	C6—C7	1.373 (3)
N1—C1	1.336 (2)	C3—H3	0.9300
N1—H1	0.83 (4)	C4—H4	0.9300
N2—H2A	0.92 (5)	C6—H6	0.9300
N2—H2B	0.93 (4)	C7—H7	0.9300
C1—C2	1.492 (2)	C8—H8A	0.9600
C2—C7	1.383 (3)	C8—H8B	0.9600
C2—C3	1.383 (3)	C8—H8C	0.9600
C5—O2—C8	118.84 (19)	O2—C5—C6	116.1 (2)
N2—N1—C1	121.47 (17)	C5—C6—C7	120.5 (2)
C1—N1—H1	124 (2)	C2—C7—C6	120.9 (2)
N2—N1—H1	114 (2)	C2—C3—H3	119.00
N1—N2—H2B	111 (3)	C4—C3—H3	119.00
H2A—N2—H2B	108 (4)	C3—C4—H4	120.00
N1—N2—H2A	107 (2)	C5—C4—H4	120.00
O1—C1—N1	121.69 (17)	C5—C6—H6	120.00
N1—C1—C2	117.14 (17)	C7—C6—H6	120.00
O1—C1—C2	121.17 (16)	C2—C7—H7	120.00
C1—C2—C7	117.86 (18)	C6—C7—H7	120.00
C3—C2—C7	118.06 (18)	O2—C8—H8A	109.00
C1—C2—C3	124.08 (16)	O2—C8—H8B	109.00
C2—C3—C4	121.4 (2)	O2—C8—H8C	109.00
C3—C4—C5	119.5 (2)	H8A—C8—H8B	109.00
O2—C5—C4	124.2 (2)	H8A—C8—H8C	109.00
C4—C5—C6	119.7 (2)	H8B—C8—H8C	109.00
C8—O2—C5—C4	−1.3 (4)	C7—C2—C3—C4	0.2 (4)
C8—O2—C5—C6	179.2 (3)	C1—C2—C7—C6	−179.6 (2)
N2—N1—C1—O1	5.3 (3)	C3—C2—C7—C6	−0.5 (4)
N2—N1—C1—C2	−174.18 (18)	C2—C3—C4—C5	0.1 (4)
O1—C1—C2—C3	−173.4 (2)	C3—C4—C5—O2	−179.7 (2)
O1—C1—C2—C7	5.7 (3)	C3—C4—C5—C6	−0.2 (4)
N1—C1—C2—C3	6.1 (3)	O2—C5—C6—C7	179.6 (2)
N1—C1—C2—C7	−174.9 (2)	C4—C5—C6—C7	−0.1 (4)
C1—C2—C3—C4	179.3 (2)	C5—C6—C7—C2	0.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.83 (4)	2.16 (4)	2.961 (3)	162 (3)
N2—H2A···O1	0.92 (5)	2.42 (4)	2.729 (2)	100 (3)
N2—H2A···O1ii	0.92 (5)	2.44 (4)	3.026 (2)	122 (3)
N2—H2B···O1iii	0.93 (4)	2.07 (4)	2.991 (2)	170 (4)
C7—H7···O1	0.93	2.47	2.781 (3)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.83 (4)	2.16 (4)	2.961 (3)	162 (3)
N2—H2A⋯O1	0.92 (5)	2.42 (4)	2.729 (2)	100 (3)
N2—H2A⋯O1ii	0.92 (5)	2.44 (4)	3.026 (2)	122 (3)
N2—H2B⋯O1iii	0.93 (4)	2.07 (4)	2.991 (2)	170 (4)
C7—H7⋯O1	0.93	2.47	2.781 (3)	100

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