3,4,5-Trihy-droxy-benzohydrazide.

In the title compound, C(7)H(8)N(2)O(4), the dihedral angle between the aromatic ring and the hydrazide grouping is 21.34 (7)°. In the crystal, the mol-ecules are linked into a three-dimensional network by O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds.

Related literature

For the biological activity of hydrazides, see: Maqsood et al. (2006 ▶). For related structures, see: Jamal et al. (2009 ▶); Saeed et al. (2008 ▶); Zareef et al. (2006 ▶).

Experimental

Crystal data

C7H8N2O4

M = 184.15

Monoclinic,

a = 3.7307 (3) Å

b = 22.8402 (18) Å

c = 8.7064 (7) Å

β = 93.290 (2)°

V = 740.65 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 273 K

0.28 × 0.21 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.963, T max = 0.973

4345 measured reflections

1352 independent reflections

1234 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.092

S = 1.09

1352 reflections

150 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034374/hb6363sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034374/hb6363Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034374/hb6363Isup3.cml

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

C7H8N2O4	F(000) = 384
Mr = 184.15	Dx = 1.651 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2464 reflections
a = 3.7307 (3) Å	θ = 3.0–28.3°
b = 22.8402 (18) Å	µ = 0.14 mm−1
c = 8.7064 (7) Å	T = 273 K
β = 93.290 (2)°	Block, colorles
V = 740.65 (10) Å3	0.28 × 0.21 × 0.20 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	1352 independent reflections
Radiation source: fine-focus sealed tube	1234 reflections with I > 2σ(I)
graphite	Rint = 0.016
ω scan	θmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −4→4
Tmin = 0.963, Tmax = 0.973	k = −27→26
4345 measured reflections	l = −10→10

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0509P)2 + 0.2069P] where P = (Fo2 + 2Fc2)/3
1352 reflections	(Δ/σ)max = 0.001
150 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.24 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	0.6088 (3)	0.49395 (4)	0.75022 (12)	0.0388 (3)
O2	0.4790 (3)	0.57014 (4)	0.97692 (11)	0.0328 (3)
H2A	0.375 (6)	0.5994 (11)	1.029 (3)	0.069 (7)*
O3	0.5451 (3)	0.68880 (5)	0.93130 (11)	0.0334 (3)
H3A	0.602 (6)	0.7255 (10)	0.907 (2)	0.061 (6)*
O4	0.7876 (3)	0.70585 (5)	0.36218 (12)	0.0402 (3)
N1	1.0268 (3)	0.62028 (5)	0.30646 (13)	0.0270 (3)
H1B	1.100 (5)	0.5854 (9)	0.329 (2)	0.037 (5)*
N2	1.1408 (4)	0.64212 (6)	0.16535 (13)	0.0283 (3)
H2C	1.285 (5)	0.6739 (9)	0.188 (2)	0.041 (5)*
H2B	0.950 (6)	0.6553 (8)	0.112 (2)	0.044 (5)*
C1	0.7698 (4)	0.63145 (6)	0.55422 (14)	0.0224 (3)
C2	0.7029 (4)	0.67156 (6)	0.66914 (15)	0.0250 (3)
H2	0.718 (4)	0.7128 (8)	0.6488 (18)	0.031 (4)*
C3	0.6093 (4)	0.65203 (6)	0.81195 (14)	0.0235 (3)
C4	0.5743 (4)	0.59242 (6)	0.84021 (14)	0.0231 (3)
C5	0.6437 (4)	0.55257 (6)	0.72421 (15)	0.0244 (3)
C6	0.7421 (4)	0.57157 (6)	0.58183 (15)	0.0246 (3)
H6	0.780 (4)	0.5428 (7)	0.5049 (19)	0.030 (4)*
C7	0.8618 (4)	0.65546 (6)	0.40269 (14)	0.0239 (3)
H1A	0.548 (6)	0.4893 (9)	0.842 (3)	0.057 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0733 (9)	0.0179 (5)	0.0271 (6)	0.0005 (5)	0.0199 (5)	0.0016 (4)
O2	0.0557 (7)	0.0214 (5)	0.0230 (5)	0.0030 (5)	0.0173 (5)	0.0034 (4)
O3	0.0602 (8)	0.0190 (5)	0.0227 (5)	−0.0028 (5)	0.0169 (5)	−0.0024 (4)
O4	0.0707 (9)	0.0224 (5)	0.0295 (6)	0.0123 (5)	0.0199 (5)	0.0066 (4)
N1	0.0409 (8)	0.0210 (6)	0.0202 (6)	0.0058 (5)	0.0118 (5)	0.0038 (4)
N2	0.0388 (8)	0.0276 (7)	0.0194 (6)	0.0021 (6)	0.0105 (5)	0.0028 (5)
C1	0.0257 (7)	0.0229 (7)	0.0190 (6)	0.0014 (5)	0.0045 (5)	0.0011 (5)
C2	0.0332 (8)	0.0188 (7)	0.0235 (7)	−0.0002 (6)	0.0063 (5)	0.0012 (5)
C3	0.0291 (8)	0.0211 (7)	0.0209 (6)	0.0002 (5)	0.0061 (5)	−0.0016 (5)
C4	0.0280 (8)	0.0225 (7)	0.0194 (6)	0.0006 (5)	0.0062 (5)	0.0023 (5)
C5	0.0317 (8)	0.0177 (7)	0.0241 (7)	0.0009 (5)	0.0055 (5)	0.0014 (5)
C6	0.0322 (8)	0.0218 (7)	0.0205 (7)	0.0027 (6)	0.0064 (5)	−0.0023 (5)
C7	0.0302 (8)	0.0211 (7)	0.0207 (6)	0.0001 (5)	0.0047 (5)	0.0000 (5)

O1—C5	1.3654 (16)	N2—H2B	0.88 (2)
O1—H1A	0.85 (2)	C1—C2	1.3897 (18)
O2—C4	1.3603 (16)	C1—C6	1.3934 (19)
O2—H2A	0.91 (3)	C1—C7	1.4869 (17)
O3—C3	1.3678 (16)	C2—C3	1.3844 (18)
O3—H3A	0.89 (2)	C2—H2	0.961 (18)
O4—C7	1.2306 (17)	C3—C4	1.3912 (19)
N1—C7	1.3363 (18)	C4—C5	1.3946 (19)
N1—N2	1.4139 (15)	C5—C6	1.3828 (19)
N1—H1B	0.860 (19)	C6—H6	0.955 (17)
N2—H2C	0.92 (2)
C5—O1—H1A	108.1 (14)	O3—C3—C2	123.28 (12)
C4—O2—H2A	107.7 (15)	O3—C3—C4	116.38 (11)
C3—O3—H3A	110.1 (14)	C2—C3—C4	120.35 (12)
C7—N1—N2	120.34 (12)	O2—C4—C3	123.55 (12)
C7—N1—H1B	124.6 (12)	O2—C4—C5	117.28 (12)
N2—N1—H1B	114.4 (12)	C3—C4—C5	119.17 (12)
N1—N2—H2C	107.3 (11)	O1—C5—C6	119.29 (12)
N1—N2—H2B	107.8 (12)	O1—C5—C4	119.76 (12)
H2C—N2—H2B	106.7 (17)	C6—C5—C4	120.95 (12)
C2—C1—C6	120.31 (12)	C5—C6—C1	119.26 (12)
C2—C1—C7	117.11 (12)	C5—C6—H6	118.0 (10)
C6—C1—C7	122.56 (12)	C1—C6—H6	122.7 (10)
C3—C2—C1	119.94 (13)	O4—C7—N1	119.12 (12)
C3—C2—H2	120.1 (9)	O4—C7—C1	122.66 (12)
C1—C2—H2	119.9 (9)	N1—C7—C1	118.21 (12)
C6—C1—C2—C3	0.2 (2)	C3—C4—C5—C6	−0.8 (2)
C7—C1—C2—C3	178.80 (13)	O1—C5—C6—C1	178.56 (13)
C1—C2—C3—O3	178.95 (13)	C4—C5—C6—C1	−0.4 (2)
C1—C2—C3—C4	−1.4 (2)	C2—C1—C6—C5	0.7 (2)
O3—C3—C4—O2	0.5 (2)	C7—C1—C6—C5	−177.85 (13)
C2—C3—C4—O2	−179.16 (13)	N2—N1—C7—O4	5.1 (2)
O3—C3—C4—C5	−178.65 (13)	N2—N1—C7—C1	−175.85 (13)
C2—C3—C4—C5	1.7 (2)	C2—C1—C7—O4	−20.3 (2)
O2—C4—C5—O1	1.0 (2)	C6—C1—C7—O4	158.29 (15)
C3—C4—C5—O1	−179.71 (13)	C2—C1—C7—N1	160.76 (13)
O2—C4—C5—C6	179.99 (13)	C6—C1—C7—N1	−20.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2i	0.85 (3)	2.09 (2)	2.8254 (14)	145.0 (19)
N1—H1B···O1ii	0.86 (2)	2.24 (2)	2.9960 (15)	146.2 (16)
O2—H2A···N2iii	0.91 (3)	1.80 (2)	2.6877 (17)	165 (2)
N2—H2B···O3iv	0.88 (2)	2.25 (2)	3.1158 (17)	167.0 (18)
N2—H2C···O4v	0.92 (2)	2.454 (18)	3.2255 (18)	141.8 (15)
O3—H3A···O4vi	0.89 (2)	1.77 (2)	2.6522 (15)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2i	0.85 (3)	2.09 (2)	2.8254 (14)	145.0 (19)
N1—H1B⋯O1ii	0.86 (2)	2.24 (2)	2.9960 (15)	146.2 (16)
O2—H2A⋯N2iii	0.91 (3)	1.80 (2)	2.6877 (17)	165 (2)
N2—H2B⋯O3iv	0.88 (2)	2.25 (2)	3.1158 (17)	167.0 (18)
N2—H2C⋯O4v	0.92 (2)	2.454 (18)	3.2255 (18)	141.8 (15)
O3—H3A⋯O4vi	0.89 (2)	1.77 (2)	2.6522 (15)	171 (2)

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