N'-(2,4-Di-nitro-phen-yl)acetohydrazide monohydrate.

In the crystal structure of the title compound, C8H8N4O5·H2O, the organic and lattice water mol-ecules are linked together via N-H⋯O and O-H⋯O hydrogen bonds. A C-H⋯O inter-action is also observed between the organic mol-ecules. These hydrogen bonds and inter-actions lead to the formation of a three-dimensional network. An intra-molecular N-H⋯O hydrogen bond also occurs. The dihedral angle between the acetyl group and the almost planar hydrazide moiety [maximum deviation from the least-squares plane is 0.209 (2) Å for one of the nitro O atoms] is 88.5 (3)°.

Related literature

For background to the biological activity of hydrazines and hydrazones, see: Zahid & Sherazi (1997 ▶); Monfared et al. (2007 ▶). For a related crystal structure, see: Okabe et al. (1993 ▶). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H8N4O5·H2O

M = 258.20

Monoclinic,

a = 7.702 (2) Å

b = 7.057 (3) Å

c = 21.550 (4) Å

β = 109.044 (19)°

V = 1107.3 (6) Å3

Z = 4

Ag Kα radiation

λ = 0.56083 Å

μ = 0.08 mm−1

T = 293 K

0.5 × 0.4 × 0.3 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

7469 measured reflections

5411 independent reflections

2771 reflections with I > 2σ(I)

R int = 0.064

2 standard reflections every 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.195

S = 0.98

5411 reflections

181 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813018916/pv2637sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018916/pv2637Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813018916/pv2637Isup3.cml

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

C8H8N4O5·H2O	F(000) = 536
Mr = 258.20	Dx = 1.549 Mg m−3
Monoclinic, P21/c	Ag Kα radiation, λ = 0.56083 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 7.702 (2) Å	θ = 9–11°
b = 7.057 (3) Å	µ = 0.08 mm−1
c = 21.550 (4) Å	T = 293 K
β = 109.044 (19)°	Prism, yellow
V = 1107.3 (6) Å3	0.5 × 0.4 × 0.3 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.064
Radiation source: fine-focus sealed tube	θmax = 28.0°, θmin = 2.2°
Graphite monochromator	h = −12→12
non–profiled ω scans	k = −11→2
7469 measured reflections	l = −36→14
5411 independent reflections	2 standard reflections every 120 min
2771 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.071	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.195	w = 1/[σ2(Fo2) + (0.0627P)2 + 0.2081P] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max = 0.004
5411 reflections	Δρmax = 0.25 e Å−3
181 parameters	Δρmin = −0.23 e Å−3
3 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: 0.027 (4)

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
OW	0.8341 (3)	0.6774 (3)	0.23696 (8)	0.0526 (5)
H1W	0.784 (4)	0.583 (3)	0.2497 (13)	0.088 (11)*
H2W	0.827 (4)	0.672 (5)	0.1972 (6)	0.091 (11)*
H2N	0.894 (4)	0.171 (4)	0.1927 (14)	0.073 (9)*
H1N	0.762 (3)	−0.050 (4)	0.2501 (11)	0.052 (7)*
C1	0.6447 (3)	0.1614 (3)	0.12985 (10)	0.0332 (4)
N2	0.7775 (3)	0.1390 (3)	0.18850 (8)	0.0416 (5)
C2	0.6778 (3)	0.2383 (3)	0.07398 (10)	0.0347 (5)
C4	0.3649 (3)	0.2020 (3)	0.00937 (10)	0.0387 (5)
N3	0.8583 (3)	0.2980 (3)	0.07563 (10)	0.0467 (5)
N4	0.2219 (3)	0.2185 (3)	−0.05403 (10)	0.0496 (5)
C3	0.5376 (3)	0.2593 (3)	0.01484 (10)	0.0383 (5)
H3	0.5615	0.3125	−0.0210	0.046*
N1	0.7353 (3)	0.0698 (3)	0.24205 (9)	0.0410 (5)
C6	0.4620 (3)	0.1034 (3)	0.12134 (10)	0.0385 (5)
H6	0.4349	0.0515	0.1568	0.046*
C5	0.3250 (3)	0.1218 (3)	0.06262 (11)	0.0422 (5)
H5	0.2065	0.0815	0.0580	0.051*
O5	0.6823 (3)	0.3600 (3)	0.27355 (9)	0.0607 (5)
C7	0.6972 (3)	0.1892 (3)	0.28405 (10)	0.0388 (5)
O4	0.2556 (3)	0.3098 (3)	−0.09698 (8)	0.0683 (6)
O2	0.8788 (3)	0.3578 (3)	0.02501 (9)	0.0723 (6)
O1	0.9859 (2)	0.2867 (3)	0.12714 (9)	0.0685 (6)
C8	0.6708 (3)	0.1000 (4)	0.34342 (10)	0.0492 (6)
H8A	0.7672	0.1403	0.3820	0.074*
H8B	0.6741	−0.0355	0.3397	0.074*
H8C	0.5542	0.1378	0.3465	0.074*
O3	0.0748 (3)	0.1398 (3)	−0.06187 (10)	0.0722 (6)

	U11	U22	U33	U12	U13	U23
OW	0.0634 (11)	0.0483 (11)	0.0435 (10)	−0.0030 (9)	0.0139 (9)	0.0001 (8)
C1	0.0400 (11)	0.0272 (10)	0.0339 (10)	0.0000 (9)	0.0142 (9)	−0.0027 (9)
N2	0.0431 (10)	0.0511 (12)	0.0333 (9)	−0.0026 (10)	0.0161 (8)	0.0035 (9)
C2	0.0404 (11)	0.0309 (11)	0.0367 (10)	−0.0045 (9)	0.0179 (9)	−0.0028 (9)
C4	0.0432 (12)	0.0331 (11)	0.0358 (10)	0.0044 (10)	0.0074 (9)	−0.0024 (9)
N3	0.0510 (12)	0.0503 (12)	0.0443 (10)	−0.0083 (10)	0.0234 (10)	0.0013 (10)
N4	0.0566 (13)	0.0416 (11)	0.0436 (11)	0.0072 (10)	0.0068 (10)	−0.0066 (10)
C3	0.0543 (14)	0.0305 (11)	0.0339 (10)	−0.0001 (10)	0.0194 (10)	0.0016 (9)
N1	0.0534 (11)	0.0387 (11)	0.0342 (9)	0.0053 (9)	0.0188 (8)	0.0067 (9)
C6	0.0458 (12)	0.0372 (12)	0.0390 (11)	−0.0009 (10)	0.0226 (10)	0.0023 (10)
C5	0.0395 (12)	0.0386 (13)	0.0498 (13)	0.0002 (10)	0.0166 (10)	−0.0039 (10)
O5	0.0877 (13)	0.0382 (10)	0.0690 (12)	0.0093 (9)	0.0431 (11)	0.0063 (9)
C7	0.0399 (11)	0.0404 (13)	0.0378 (11)	0.0004 (10)	0.0152 (9)	0.0037 (10)
O4	0.0883 (14)	0.0697 (13)	0.0383 (9)	0.0014 (11)	0.0090 (9)	0.0087 (10)
O2	0.0695 (12)	0.1000 (16)	0.0573 (11)	−0.0166 (11)	0.0342 (10)	0.0137 (11)
O1	0.0465 (10)	0.1019 (16)	0.0551 (11)	−0.0231 (10)	0.0138 (9)	0.0105 (11)
C8	0.0548 (14)	0.0557 (16)	0.0397 (12)	0.0029 (12)	0.0188 (11)	0.0065 (11)
O3	0.0496 (10)	0.0774 (14)	0.0732 (13)	−0.0013 (11)	−0.0025 (9)	−0.0012 (11)

OW—H1W	0.856 (10)	N4—O3	1.223 (3)
OW—H2W	0.841 (9)	N4—O4	1.224 (3)
C1—N2	1.351 (3)	C3—H3	0.9300
C1—C2	1.418 (3)	N1—C7	1.338 (3)
C1—C6	1.419 (3)	N1—H1N	0.88 (3)
N2—N1	1.386 (2)	C6—C5	1.364 (3)
N2—H2N	0.90 (3)	C6—H6	0.9300
C2—C3	1.384 (3)	C5—H5	0.9300
C2—N3	1.442 (3)	O5—C7	1.225 (3)
C4—C3	1.358 (3)	C7—C8	1.498 (3)
C4—C5	1.400 (3)	C8—H8A	0.9600
C4—N4	1.453 (3)	C8—H8B	0.9600
N3—O1	1.222 (2)	C8—H8C	0.9600
N3—O2	1.227 (2)
H1W—OW—H2W	114 (2)	C4—C3—H3	120.1
N2—C1—C2	123.22 (18)	C2—C3—H3	120.1
N2—C1—C6	120.24 (18)	C7—N1—N2	120.3 (2)
C2—C1—C6	116.53 (18)	C7—N1—H1N	124.5 (16)
C1—N2—N1	120.55 (18)	N2—N1—H1N	113.5 (16)
C1—N2—H2N	119.4 (18)	C5—C6—C1	121.78 (19)
N1—N2—H2N	120.0 (18)	C5—C6—H6	119.1
C3—C2—C1	121.36 (18)	C1—C6—H6	119.1
C3—C2—N3	116.61 (18)	C6—C5—C4	119.25 (19)
C1—C2—N3	122.03 (18)	C6—C5—H5	120.4
C3—C4—C5	121.3 (2)	C4—C5—H5	120.4
C3—C4—N4	118.6 (2)	O5—C7—N1	121.5 (2)
C5—C4—N4	120.1 (2)	O5—C7—C8	122.7 (2)
O1—N3—O2	122.08 (19)	N1—C7—C8	115.7 (2)
O1—N3—C2	119.13 (17)	C7—C8—H8A	109.5
O2—N3—C2	118.79 (19)	C7—C8—H8B	109.5
O3—N4—O4	123.4 (2)	H8A—C8—H8B	109.5
O3—N4—C4	118.5 (2)	C7—C8—H8C	109.5
O4—N4—C4	118.1 (2)	H8A—C8—H8C	109.5
C4—C3—C2	119.74 (19)	H8B—C8—H8C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
OW—H1W···O5	0.86 (1)	1.91 (1)	2.759 (3)	175 (3)
OW—H2W···O4i	0.84 (1)	2.05 (1)	2.868 (3)	165 (3)
N1—H1N···OWii	0.88 (3)	2.04 (3)	2.883 (3)	160 (2)
N2—H2N···O1	0.90 (3)	1.96 (3)	2.607 (2)	128 (2)
N2—H2N···OWiii	0.90 (3)	2.15 (3)	2.910 (3)	142 (2)
C6—H6···O5iv	0.93	2.40	3.310 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
OW—H1W⋯O5	0.86 (1)	1.91 (1)	2.759 (3)	175 (3)
OW—H2W⋯O4i	0.84 (1)	2.05 (1)	2.868 (3)	165 (3)
N1—H1N⋯OW ii	0.88 (3)	2.04 (3)	2.883 (3)	160 (2)
N2—H2N⋯O1	0.90 (3)	1.96 (3)	2.607 (2)	128 (2)
N2—H2N⋯OW iii	0.90 (3)	2.15 (3)	2.910 (3)	142 (2)
C6—H6⋯O5iv	0.93	2.40	3.310 (3)	165

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