2-Cyano-N′-(5-hy­droxy-2-nitro­benzyl­idene)acetohydrazide monohydrate

Li, H.; Ni, X.

doi:10.1107/S1600536811025463

organic compounds

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Volume 67| Part 8| August 2011| Page o2002

doi:10.1107/S1600536811025463

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2-Cyano-N′-(5-hydroxy-2-nitrobenzylidene)acetohydrazide monohydrate

Hongbo Li ^a ^* and Xiaocheng Ni ^a

^aCollege of Chemistry and Biology Engineering, Yancheng Institute of Technology, Yancheng 224051, People's Republic of China
^*Correspondence e-mail: hbli@ycit.edu.cn

(Received 25 June 2011; accepted 28 June 2011; online 9 July 2011)

The title compound, C₁₀H₈N₄O₄·H₂O, was obtained by the reaction of 5-hydroxy-2-nitrobenzaldehyde with cyanoacetohydrazide 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, molecules 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_r = 266.22
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.054
wR(F²) = 0.148
S = 1.04
2531 reflections
184 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+2, -y+1, -z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811025463/qm2014sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811025463/qm2014Isup3.cml

checkCIF report

Comment top

Recently, a great number of hydrazones derived from the reaction of benzaldehyde and its derivatives with benzohydrazides have been reported (Wang et al., 2011; Hashemian et al., 2011; Singh & Singh, 2010; Ahmad et al., 2010). To the best of our knowledge, the hydrazones derived from cyanoacetohydrazide have never been reported so far. In this paper, the title new hydrazone compound, (I), is reported.

The compound contains a hydrazone molecule and a water molecule (Fig. 1). The non-hydrogen atoms of the hydrazone molecule are approximately coplanar, with mean deviation from the least-squares plane of 0.056 (3) Å. In the crystal structure, molecules are linked by intermolecular N—H···O, O—H···O, and O—H···N hydrogen bonds (Table 1), generating a three-dimensional network (Fig. 2).

Related literature top

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

Experimental top

The title compound was obtained by the reaction of equimolar quantities (1.0 mmol each) of 5-hydroxy-2-nitrobenzaldehyde with cyanoacetohydrazide in methanol. Single crystals suitable for X-ray diffraction were obtained by the slow evaporation of the solution containing the compound in open air.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms. O—H···O hydrogen bond is shown as a dashed line.
	Fig. 2. The packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

2-Cyano-N'-(5-hydroxy-2-nitrobenzylidene)acetohydrazide monohydrate top

Crystal data top

C₁₀H₈N₄O₄·H₂O	F(000) = 552
M_r = 266.22	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0727P)² + 0.3422P] where P = (F_o² + 2F_c²)/3
2531 reflections	(Δ/σ)_max = 0.001
184 parameters	Δρ_max = 0.43 e Å⁻³
5 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₀H₈N₄O₄·H₂O	V = 1191.7 (3) Å³
M_r = 266.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.663 (1) Å	µ = 0.12 mm⁻¹
b = 13.238 (2) Å	T = 298 K
c = 19.305 (2) Å	0.27 × 0.23 × 0.23 mm
β = 90.312 (3)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	2531 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1935 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.973	R_int = 0.028
8851 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	5 restraints
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.43 e Å⁻³
2531 reflections	Δρ_min = −0.20 e Å⁻³
184 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y+1/2, −z+1/2; (ii) x−1/2, −y+3/2, z+1/2; (iii) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₄O₄·H₂O
M_r	266.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	4.663 (1), 13.238 (2), 19.305 (2)
β (°)	90.312 (3)
V (Å³)	1191.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.27 × 0.23 × 0.23

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.968, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	8851, 2531, 1935
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.148, 1.04
No. of reflections	2531
No. of parameters	184
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.20

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···N4ⁱ	0.839 (10)	2.323 (16)	3.117 (4)	158 (3)
O5—H5A···O1ⁱⁱ	0.840 (10)	2.224 (15)	3.017 (3)	157 (3)
O4—H4···O5	0.856 (10)	1.854 (12)	2.700 (3)	170 (3)
N3—H3A···O3ⁱⁱⁱ	0.898 (10)	1.983 (10)	2.880 (2)	177 (2)

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x−1/2, −y+3/2, z+1/2; (iii) −x+2, −y+1, −z.

References

Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o1022. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hashemian, S., Ghaeinee, V. & Notash, B. (2011). Acta Cryst. E67, o171. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, V. P. & Singh, S. (2010). Acta Cryst. E66, o1172. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, F., Liu, D.-Y., Wang, H.-B., Meng, X.-S. & Kang, T.-G. (2011). Acta Cryst. E67, o810. Web of Science CSD CrossRef IUCr Journals Google Scholar

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2002

doi:10.1107/S1600536811025463

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