2-Cyano-N'-(5-hy-droxy-2-nitro-benzyl-idene)acetohydrazide monohydrate.

The title compound, C(10)H(8)N(4)O(4)·H(2)O, was obtained by the reaction of 5-hy-droxy-2-nitro-benzaldehyde with cyano-acetohydrazide in methanol. The non-H atoms of the hydrazone molecule are approximately coplanar, with a mean deviation from the least-squares plane of 0.056 Å. In the crystal, mol-ecules are linked by N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds, generating a three-dimensional network.

Related literature

For the structures of hydrazones, see: Wang et al. (2011 ▶); Hashemian et al. (2011 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶).

Experimental

Crystal data

C10H8N4O4·H2O

M = 266.22

Monoclinic,

a = 4.663 (1) Å

b = 13.238 (2) Å

c = 19.305 (2) Å

β = 90.312 (3)°

V = 1191.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 298 K

0.27 × 0.23 × 0.23 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.968, T max = 0.973

8851 measured reflections

2531 independent reflections

1935 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.148

S = 1.04

2531 reflections

184 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811025463/qm2014sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025463/qm2014Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025463/qm2014Isup3.cml

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

C10H8N4O4·H2O	F(000) = 552
Mr = 266.22	Dx = 1.484 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 4.663 (1) Å	Cell parameters from 2122 reflections
b = 13.238 (2) Å	θ = 2.6–26.6°
c = 19.305 (2) Å	µ = 0.12 mm−1
β = 90.312 (3)°	T = 298 K
V = 1191.7 (3) Å3	Block, colorless
Z = 4	0.27 × 0.23 × 0.23 mm

Bruker SMART 1K CCD area-detector diffractometer	2531 independent reflections
Radiation source: fine-focus sealed tube	1935 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −5→5
Tmin = 0.968, Tmax = 0.973	k = −16→16
8851 measured reflections	l = −24→23

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0727P)2 + 0.3422P] where P = (Fo2 + 2Fc2)/3
2531 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.43 e Å−3
5 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
N1	0.1870 (4)	0.73554 (14)	−0.16790 (9)	0.0507 (5)
N2	0.5017 (3)	0.64853 (11)	0.03310 (8)	0.0366 (4)
N3	0.7235 (3)	0.57994 (11)	0.03500 (8)	0.0369 (4)
N4	0.9875 (6)	0.5194 (2)	0.26634 (12)	0.0898 (8)
O1	0.3932 (4)	0.67914 (16)	−0.16953 (9)	0.0813 (6)
O2	0.0556 (5)	0.75595 (16)	−0.22076 (9)	0.0877 (7)
O3	1.0378 (3)	0.48653 (11)	0.09451 (7)	0.0476 (4)
O4	−0.2421 (3)	0.91461 (12)	0.07021 (8)	0.0574 (4)
O5	0.0680 (5)	0.8597 (2)	0.18259 (10)	0.0919 (7)
C1	0.2056 (4)	0.75195 (13)	−0.03818 (9)	0.0350 (4)
C2	0.0916 (4)	0.77958 (14)	−0.10307 (10)	0.0403 (5)
C3	−0.1218 (5)	0.85279 (15)	−0.10828 (12)	0.0481 (5)
H3	−0.1921	0.8711	−0.1517	0.058*
C4	−0.2291 (5)	0.89799 (15)	−0.05048 (12)	0.0489 (5)
H4A	−0.3714	0.9469	−0.0545	0.059*
C5	−0.1244 (4)	0.87064 (14)	0.01452 (11)	0.0424 (5)
C6	0.0926 (4)	0.79932 (13)	0.01966 (10)	0.0378 (4)
H6	0.1646	0.7828	0.0632	0.045*
C7	0.4343 (4)	0.67707 (13)	−0.02755 (9)	0.0362 (4)
H7	0.5302	0.6505	−0.0655	0.043*
C8	0.8365 (4)	0.54622 (14)	0.09432 (10)	0.0379 (4)
C9	0.7002 (5)	0.58300 (19)	0.16020 (10)	0.0589 (6)
H9A	0.6945	0.6562	0.1602	0.071*
H9B	0.5047	0.5583	0.1628	0.071*
C10	0.8611 (6)	0.54791 (19)	0.21982 (12)	0.0608 (6)
H3A	0.804 (5)	0.5585 (18)	−0.0045 (8)	0.073*
H4	−0.158 (6)	0.891 (2)	0.1062 (10)	0.091*
H5A	−0.017 (5)	0.839 (2)	0.2181 (10)	0.091*
H5B	0.220 (4)	0.889 (2)	0.1943 (14)	0.091*

	U11	U22	U33	U12	U13	U23
N1	0.0566 (12)	0.0555 (11)	0.0398 (10)	−0.0081 (9)	−0.0049 (8)	0.0066 (8)
N2	0.0351 (9)	0.0339 (8)	0.0408 (9)	0.0058 (6)	−0.0004 (7)	−0.0017 (6)
N3	0.0367 (9)	0.0388 (8)	0.0352 (8)	0.0084 (7)	0.0004 (6)	−0.0012 (6)
N4	0.1006 (19)	0.117 (2)	0.0512 (13)	0.0011 (16)	−0.0282 (13)	0.0015 (13)
O1	0.0820 (13)	0.1149 (16)	0.0470 (10)	0.0336 (12)	−0.0046 (9)	−0.0139 (10)
O2	0.1152 (17)	0.1065 (15)	0.0413 (10)	0.0179 (12)	−0.0188 (10)	0.0071 (9)
O3	0.0456 (8)	0.0548 (8)	0.0423 (8)	0.0165 (7)	−0.0015 (6)	0.0026 (6)
O4	0.0541 (10)	0.0521 (9)	0.0661 (11)	0.0165 (7)	0.0021 (8)	−0.0071 (8)
O5	0.1056 (17)	0.123 (2)	0.0469 (10)	0.0166 (14)	0.0030 (10)	0.0008 (11)
C1	0.0313 (10)	0.0330 (9)	0.0407 (10)	−0.0045 (7)	−0.0021 (8)	0.0031 (7)
C2	0.0410 (11)	0.0392 (10)	0.0406 (10)	−0.0081 (8)	−0.0041 (8)	0.0065 (8)
C3	0.0465 (12)	0.0432 (11)	0.0543 (12)	−0.0048 (9)	−0.0138 (10)	0.0141 (9)
C4	0.0405 (12)	0.0360 (10)	0.0700 (14)	0.0044 (8)	−0.0092 (10)	0.0097 (10)
C5	0.0377 (11)	0.0321 (9)	0.0575 (12)	−0.0025 (8)	−0.0001 (9)	−0.0012 (8)
C6	0.0341 (10)	0.0347 (9)	0.0447 (10)	0.0002 (8)	−0.0033 (8)	0.0031 (8)
C7	0.0356 (10)	0.0368 (9)	0.0362 (10)	0.0000 (8)	0.0014 (7)	0.0001 (7)
C8	0.0378 (11)	0.0378 (10)	0.0380 (10)	0.0020 (8)	−0.0010 (8)	−0.0015 (8)
C9	0.0643 (15)	0.0749 (16)	0.0375 (11)	0.0229 (12)	−0.0052 (10)	−0.0076 (10)
C10	0.0675 (16)	0.0742 (16)	0.0405 (12)	0.0013 (13)	−0.0063 (11)	−0.0082 (11)

N1—O2	1.218 (2)	C1—C2	1.407 (3)
N1—O1	1.218 (2)	C1—C7	1.470 (2)
N1—C2	1.453 (3)	C2—C3	1.392 (3)
N2—C7	1.268 (2)	C3—C4	1.363 (3)
N2—N3	1.377 (2)	C3—H3	0.9300
N3—C8	1.335 (2)	C4—C5	1.392 (3)
N3—H3A	0.898 (10)	C4—H4A	0.9300
N4—C10	1.136 (3)	C5—C6	1.387 (3)
O3—C8	1.227 (2)	C6—H6	0.9300
O4—C5	1.343 (3)	C7—H7	0.9300
O4—H4	0.856 (10)	C8—C9	1.506 (3)
O5—H5A	0.840 (10)	C9—C10	1.447 (3)
O5—H5B	0.839 (10)	C9—H9A	0.9700
C1—C6	1.387 (3)	C9—H9B	0.9700
O2—N1—O1	120.5 (2)	C5—C4—H4A	120.2
O2—N1—C2	118.5 (2)	O4—C5—C6	122.62 (18)
O1—N1—C2	120.92 (17)	O4—C5—C4	117.80 (18)
C7—N2—N3	113.79 (15)	C6—C5—C4	119.59 (19)
C8—N3—N2	122.43 (15)	C1—C6—C5	122.01 (18)
C8—N3—H3A	117.2 (17)	C1—C6—H6	119.0
N2—N3—H3A	120.3 (17)	C5—C6—H6	119.0
C5—O4—H4	108 (2)	N2—C7—C1	120.39 (17)
H5A—O5—H5B	110 (2)	N2—C7—H7	119.8
C6—C1—C2	117.14 (17)	C1—C7—H7	119.8
C6—C1—C7	118.09 (16)	O3—C8—N3	121.08 (17)
C2—C1—C7	124.77 (17)	O3—C8—C9	122.14 (17)
C3—C2—C1	120.78 (19)	N3—C8—C9	116.76 (17)
C3—C2—N1	116.07 (18)	C10—C9—C8	110.41 (19)
C1—C2—N1	123.15 (18)	C10—C9—H9A	109.6
C4—C3—C2	120.77 (19)	C8—C9—H9A	109.6
C4—C3—H3	119.6	C10—C9—H9B	109.6
C2—C3—H3	119.6	C8—C9—H9B	109.6
C3—C4—C5	119.69 (19)	H9A—C9—H9B	108.1
C3—C4—H4A	120.2	N4—C10—C9	179.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···N4i	0.84 (1)	2.32 (2)	3.117 (4)	158 (3)
O5—H5A···O1ii	0.84 (1)	2.22 (2)	3.017 (3)	157 (3)
O4—H4···O5	0.86 (1)	1.85 (1)	2.700 (3)	170 (3)
N3—H3A···O3iii	0.90 (1)	1.98 (1)	2.880 (2)	177 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯N4i	0.84 (1)	2.32 (2)	3.117 (4)	158 (3)
O5—H5A⋯O1ii	0.84 (1)	2.22 (2)	3.017 (3)	157 (3)
O4—H4⋯O5	0.86 (1)	1.85 (1)	2.700 (3)	170 (3)
N3—H3A⋯O3iii	0.90 (1)	1.98 (1)	2.880 (2)	177 (2)

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