4-Hydroxy-benzohydrazide.

In the title compound, C(7)H(8)N(2)O(2), the mean planes of the benzene ring and the planar hydrazide group are inclined at 25.75 (6)° with respect to each other. The structure is stabilized by inter-molecular N-H⋯O and O-H⋯N hydrogen bonds.

Related literature

For related structures see: Ashiq, Jamal et al. (2008 ▶, 2009 ▶); Hanif et al. (2007 ▶); 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 ▶); Maqsood et al. (2006 ▶).

Experimental

Crystal data

C7H8N2O2

M = 152.15

Monoclinic,

a = 5.0587 (2) Å

b = 17.2149 (9) Å

c = 7.8178 (5) Å

β = 93.489 (2)°

V = 679.55 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.32 × 0.18 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.965, T max = 0.992

7324 measured reflections

1697 independent reflections

1348 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.118

S = 1.06

1697 reflections

107 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.20 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/S1600536809025094/pv2171sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025094/pv2171Isup2.hkl

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

C7H8N2O2	F(000) = 320
Mr = 152.15	Dx = 1.487 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2993 reflections
a = 5.0587 (2) Å	θ = 2.9–28.3°
b = 17.2149 (9) Å	µ = 0.11 mm−1
c = 7.8178 (5) Å	T = 296 K
β = 93.489 (2)°	Needle, colourless
V = 679.55 (6) Å3	0.32 × 0.18 × 0.12 mm
Z = 4

Bruker Kappa APEX2 CCD diffractometer	1697 independent reflections
Radiation source: fine-focus sealed tube	1348 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→6
Tmin = 0.965, Tmax = 0.992	k = −22→23
7324 measured reflections	l = −10→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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0613P)2 + 0.1539P] where P = (Fo2 + 2Fc2)/3
1697 reflections	(Δ/σ)max < 0.001
107 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.20 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
O1	0.7565 (2)	0.04052 (5)	0.14740 (17)	0.0478 (3)
H1A	0.8946	0.0291	0.2020	0.072*
O2	0.36833 (17)	0.38981 (5)	0.10180 (14)	0.0364 (3)
N1	0.8045 (2)	0.40995 (6)	0.15266 (16)	0.0331 (3)
H1	0.9606	0.3900	0.1554	0.040*
N2	0.7783 (2)	0.49074 (6)	0.1772 (2)	0.0381 (3)
H12	0.647 (4)	0.4969 (10)	0.247 (2)	0.046*
H22	0.736 (3)	0.5124 (10)	0.075 (2)	0.046*
C1	0.6499 (2)	0.27877 (7)	0.12927 (16)	0.0244 (3)
C2	0.4705 (2)	0.22850 (7)	0.04589 (17)	0.0299 (3)
H2	0.3217	0.2486	−0.0145	0.036*
C3	0.5095 (3)	0.14912 (8)	0.05121 (18)	0.0335 (3)
H3	0.3892	0.1161	−0.0066	0.040*
C4	0.7289 (3)	0.11891 (7)	0.14320 (18)	0.0304 (3)
C5	0.9081 (2)	0.16847 (7)	0.22869 (19)	0.0325 (3)
H5	1.0545	0.1484	0.2915	0.039*
C6	0.8685 (2)	0.24751 (7)	0.22038 (18)	0.0307 (3)
H6	0.9904	0.2805	0.2768	0.037*
C7	0.5947 (2)	0.36334 (7)	0.12527 (16)	0.0255 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0407 (6)	0.0216 (5)	0.0792 (9)	0.0012 (4)	−0.0124 (5)	0.0027 (5)
O2	0.0201 (4)	0.0278 (5)	0.0605 (7)	0.0024 (3)	−0.0032 (4)	0.0034 (4)
N1	0.0203 (5)	0.0213 (5)	0.0574 (7)	0.0009 (4)	−0.0008 (5)	−0.0007 (5)
N2	0.0305 (6)	0.0206 (5)	0.0627 (9)	−0.0015 (4)	−0.0020 (6)	0.0009 (5)
C1	0.0202 (5)	0.0231 (5)	0.0299 (6)	0.0007 (4)	0.0011 (4)	0.0016 (5)
C2	0.0238 (6)	0.0277 (6)	0.0372 (7)	−0.0002 (4)	−0.0061 (5)	0.0024 (5)
C3	0.0299 (6)	0.0277 (6)	0.0418 (8)	−0.0046 (5)	−0.0057 (5)	−0.0017 (5)
C4	0.0288 (6)	0.0208 (6)	0.0418 (7)	−0.0002 (5)	0.0037 (5)	0.0024 (5)
C5	0.0240 (6)	0.0274 (6)	0.0450 (8)	0.0033 (5)	−0.0061 (5)	0.0045 (5)
C6	0.0238 (6)	0.0266 (6)	0.0408 (7)	−0.0009 (5)	−0.0067 (5)	−0.0006 (5)
C7	0.0210 (5)	0.0241 (6)	0.0311 (6)	0.0011 (4)	0.0004 (4)	0.0013 (5)

O1—C4	1.3569 (14)	C1—C7	1.4824 (16)
O1—H1A	0.8200	C2—C3	1.3809 (17)
O2—C7	1.2356 (14)	C2—H2	0.9300
N1—C7	1.3376 (15)	C3—C4	1.3866 (18)
N1—N2	1.4113 (15)	C3—H3	0.9300
N1—H1	0.8600	C4—C5	1.3864 (18)
N2—H12	0.89 (2)	C5—C6	1.3762 (17)
N2—H22	0.90 (2)	C5—H5	0.9300
C1—C6	1.3870 (17)	C6—H6	0.9300
C1—C2	1.3876 (17)
C4—O1—H1A	109.5	C2—C3—H3	120.2
C7—N1—N2	122.18 (10)	C4—C3—H3	120.2
C7—N1—H1	118.9	O1—C4—C5	122.50 (12)
N2—N1—H1	118.9	O1—C4—C3	117.60 (12)
N1—N2—H12	106.3 (11)	C5—C4—C3	119.90 (12)
N1—N2—H22	108.1 (11)	C6—C5—C4	119.78 (12)
H12—N2—H22	110.4 (17)	C6—C5—H5	120.1
C6—C1—C2	118.52 (11)	C4—C5—H5	120.1
C6—C1—C7	122.35 (11)	C5—C6—C1	121.13 (12)
C2—C1—C7	119.05 (11)	C5—C6—H6	119.4
C3—C2—C1	120.98 (12)	C1—C6—H6	119.4
C3—C2—H2	119.5	O2—C7—N1	121.45 (11)
C1—C2—H2	119.5	O2—C7—C1	122.48 (11)
C2—C3—C4	119.68 (12)	N1—C7—C1	116.04 (10)
C6—C1—C2—C3	−0.8 (2)	C2—C1—C6—C5	0.0 (2)
C7—C1—C2—C3	−177.79 (12)	C7—C1—C6—C5	176.81 (12)
C1—C2—C3—C4	1.0 (2)	N2—N1—C7—O2	7.9 (2)
C2—C3—C4—O1	178.80 (12)	N2—N1—C7—C1	−170.63 (12)
C2—C3—C4—C5	−0.2 (2)	C6—C1—C7—O2	−152.94 (13)
O1—C4—C5—C6	−179.61 (13)	C2—C1—C7—O2	23.90 (18)
C3—C4—C5—C6	−0.6 (2)	C6—C1—C7—N1	25.57 (18)
C4—C5—C6—C1	0.8 (2)	C2—C1—C7—N1	−157.60 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.13	2.9243 (14)	153
O1—H1A···N2ii	0.82	1.98	2.7852 (16)	174
N2—H12···O1iii	0.89 (2)	2.37 (2)	3.223 (2)	160
N2—H22···O2iv	0.90 (2)	2.22 (2)	3.056 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.13	2.9243 (14)	153
O1—H1A⋯N2ii	0.82	1.98	2.7852 (16)	174
N2—H12⋯O1iii	0.89 (2)	2.37 (2)	3.223 (2)	160
N2—H22⋯O2iv	0.90 (2)	2.22 (2)	3.056 (2)	155

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