N′-(4-Hydroxy­benzyl­idene)aceto­hydrazide monohydrate

Lv, L.-P.; Yu, T.-M.; Yu, W.-B.; Li, W.-W.; Hu, X.-C.

doi:10.1107/S160053680902892X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o2007

doi:10.1107/S160053680902892X

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N′-(4-Hydroxybenzylidene)acetohydrazide monohydrate

Lu-Ping Lv,^a Tie-Ming Yu,^a Wen-Bo Yu,^a Wei-Wei Li ^a and Xian-Chao Hu ^b ^*

^aDepartment of Chemical Engineering, Hangzhou Vocational and Technical College, Hangzhou 310018, People's Republic of China, and ^bResearch Center of Analysis and Measurement, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: zgdhxc@126.com

(Received 7 July 2009; accepted 22 July 2009; online 29 July 2009)

In the title compound, C₉H₁₀N₂O₂·H₂O, the molecular skeleton of the acetohydrazide molecule is nearly planar [within 0.014 (1) Å]. The molecule adopts a trans configuration with respect to the C=N bond, while the side chain is slightly twisted away from the attached ring, forming a dihedral angle of 9.975 (8)°. The crystal packing exhibits a three-dimensional network composed from alternating acetohydrazide molecules and uncoordinated water molecules, which interact via N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds. A C—H⋯π interaction is also present.

Related literature

For general background to the analytical applications of Schiff bases, see: Ciemerman et al. (1997 ). For their mild bacteriostatic activity and potential use as oral iron-chelating drugs for the treatment of genetic disorders such as thalassemia, see: Offe et al. (1952 ); Richardson et al. (1988 ). For a related structure, see: Li & Jian (2008 ); Tamboura et al. (2009 ).

Experimental

Crystal data

C₉H₁₀N₂O₂·H₂O
M_r = 196.21
Monoclinic, P 2₁ /n
a = 8.352 (2) Å
b = 10.146 (3) Å
c = 12.328 (3) Å
β = 105.353 (3)°
V = 1007.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 223 K
0.23 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.969, T_max = 0.976
4820 measured reflections
1764 independent reflections
1569 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.100
S = 1.06
1764 reflections
147 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	2.00	2.7477 (15)	152
N2—H2A⋯O1Wⁱⁱ	0.86	1.96	2.8060 (17)	166
O1W—H1F⋯O2	0.88 (2)	1.92 (2)	2.7600 (17)	159 (2)
O1W—H1E⋯O1ⁱⁱⁱ	0.85 (2)	2.01 (2)	2.8241 (17)	161 (2)
O1—H1⋯N1ⁱ	0.82	2.54	3.1864 (16)	137
C9—H9B⋯Cg1^iv	0.96	2.74	3.519 (2)	138
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-1, y+1, z; (iv) -x+1, -y, -z+1. Cg1 is the centroid of the C1–C6 ring.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902892X/bg2278sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902892X/bg2278Isup2.hkl

checkCIF report

Comment top

Schiff bases have attracted much attention due to their possibility of analytical application (Ciemerman et al., 1997). They are also important ligands, which have been reported to have mild bacteriostatic activity and potential oral iron-chelating drugs for genetic disorders such as thalassemia (Offe et al., 1952, Richardson et al., 1988). Metal complexes based on Schiff bases have received considerable attention because they can be utilized as model compounds of active centres in various complexes (Tamboura et al., 2009). We report here the crystal structure of the title compound (Fig. 1).

In the title compound,C₉H₁₀N₂O₂ .H₂O, (I) the molecular skeleton is nearly planar. The molecule adopts a trans configuration with respect to the C═N bond, while the side chain is slightly twisted away from the attached ring. The dihedral angle between these two essentially planar units is 9.975 (8)°. Bond lengths and angles are comparable to those observed for N'-[1-(4-methoxyphenyl)ethylidene]acetohydrazide (Li et al., 2008).

The crystal packing exhibits a three-dimensional network composed from alternating molecules of (I) and crystalline water, which interact via N-H···O, O-H···O and O-H···N hydrogen bonds. In addition, a intermolecular C—H···π interactions is observed (Table 1 and Fig 2).

Related literature top

For general background to the analytical applications of Schiff bases, see: Ciemerman et al. (1997). For their mild bacteriostatic activity and potential use asoral iron-chelating drugs for the treatment of genetic disorders such as thalassemia, see: Offe et al. (1952); Richardson et al. (1988). For a related structure, see: Li & Jian (2008); Tamboura et al. (2009). Cg1 is the centroid of the C1–C6 ring.

Experimental top

4-Hydroxybenzaldehyde (1.22 g, 0.01 mol) and acetohydrazide (0.74 g, 0.01 mol) were dissolved in stirred methanol (20 ml) and left for 2.5 h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 95% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature (m.p. 435–437 K).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 40% probability level. Dashed lines indicate hydrogen bonds.
	Fig. 2. Crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

N'-(4-Hydroxybenzylidene)acetohydrazide monohydrate top

Crystal data top

C₉H₁₀N₂O₂·H₂O	F(000) = 416
M_r = 196.21	D_x = 1.294 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1764 reflections
a = 8.352 (2) Å	θ = 2.6–25.0°
b = 10.146 (3) Å	µ = 0.10 mm⁻¹
c = 12.328 (3) Å	T = 223 K
β = 105.353 (3)°	Block, colourless
V = 1007.3 (5) Å³	0.23 × 0.21 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	1764 independent reflections
Radiation source: fine-focus sealed tube	1569 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→9
T_min = 0.969, T_max = 0.976	k = −10→12
4820 measured reflections	l = −14→14

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0527P)² + 0.2585P] where P = (F_o² + 2F_c²)/3
1764 reflections	(Δ/σ)_max < 0.001
147 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₉H₁₀N₂O₂·H₂O	V = 1007.3 (5) Å³
M_r = 196.21	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.352 (2) Å	µ = 0.10 mm⁻¹
b = 10.146 (3) Å	T = 223 K
c = 12.328 (3) Å	0.23 × 0.21 × 0.20 mm
β = 105.353 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1764 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1569 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.976	R_int = 0.015
4820 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.18 e Å⁻³
1764 reflections	Δρ_min = −0.22 e Å⁻³
147 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
C1	0.96500 (16)	0.24160 (13)	0.32475 (11)	0.0320 (3)
C2	0.86072 (18)	0.34460 (14)	0.27501 (11)	0.0376 (3)
H2	0.8381	0.3587	0.1979	0.046 (4)*
C3	0.79116 (17)	0.42545 (14)	0.33983 (12)	0.0370 (3)
H3	0.7221	0.4941	0.3060	0.046 (4)*
C4	0.82307 (16)	0.40561 (13)	0.45606 (11)	0.0319 (3)
C5	0.92557 (17)	0.30058 (14)	0.50398 (11)	0.0348 (5)	0.998 (6)
H5	0.9473	0.2853	0.5809	0.040 (4)*
C6	0.99522 (17)	0.21901 (13)	0.43931 (11)	0.0352 (3)
H6	1.0623	0.1490	0.4725	0.041 (4)*
C7	0.75676 (16)	0.49358 (13)	0.52741 (11)	0.0337 (3)
H7	0.7852	0.4793	0.6047	0.041 (4)*
C8	0.51412 (16)	0.77123 (13)	0.52939 (11)	0.0321 (3)
C9	0.47333 (19)	0.85289 (14)	0.61982 (12)	0.0408 (4)
H9A	0.5276	0.8165	0.6921	0.094 (7)*
H9B	0.3554	0.8528	0.6100	0.104 (8)*
H9C	0.5109	0.9416	0.6153	0.086 (7)*
N1	0.66075 (13)	0.58964 (11)	0.48641 (9)	0.0333 (3)
N2	0.61346 (14)	0.66803 (11)	0.56438 (9)	0.0329 (3)
H2A	0.6479	0.6504	0.6350	0.045 (4)*
O1	1.04051 (13)	0.16176 (10)	0.26415 (8)	0.0421 (3)
H1	1.0135	0.1844	0.1979	0.080 (7)*
O2	0.45976 (13)	0.79883 (10)	0.42813 (8)	0.0436 (3)
O1W	0.17157 (17)	0.90361 (12)	0.29134 (10)	0.0527 (3)
H1E	0.146 (3)	0.984 (2)	0.2989 (18)	0.075 (7)*
H1F	0.260 (3)	0.886 (2)	0.3465 (19)	0.078 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0344 (7)	0.0292 (7)	0.0343 (7)	−0.0020 (5)	0.0123 (6)	−0.0026 (5)
C2	0.0447 (8)	0.0401 (8)	0.0294 (7)	0.0043 (6)	0.0122 (6)	0.0036 (6)
C3	0.0396 (7)	0.0355 (7)	0.0367 (7)	0.0061 (6)	0.0117 (6)	0.0040 (6)
C4	0.0313 (7)	0.0317 (7)	0.0338 (7)	−0.0048 (5)	0.0106 (5)	−0.0023 (5)
C5	0.0381 (8)	0.0378 (9)	0.0289 (7)	−0.0024 (6)	0.0096 (6)	0.0011 (6)
C6	0.0372 (7)	0.0315 (7)	0.0366 (7)	0.0026 (6)	0.0091 (6)	0.0035 (6)
C7	0.0343 (7)	0.0361 (7)	0.0314 (7)	−0.0043 (6)	0.0101 (5)	−0.0026 (5)
C8	0.0319 (7)	0.0313 (7)	0.0350 (7)	−0.0061 (5)	0.0121 (6)	−0.0004 (5)
C9	0.0474 (9)	0.0345 (8)	0.0435 (8)	−0.0027 (6)	0.0173 (7)	−0.0066 (6)
N1	0.0350 (6)	0.0347 (6)	0.0324 (6)	−0.0024 (5)	0.0129 (5)	−0.0048 (5)
N2	0.0363 (6)	0.0352 (6)	0.0281 (6)	−0.0004 (5)	0.0103 (5)	−0.0035 (4)
O1	0.0545 (7)	0.0391 (6)	0.0353 (6)	0.0119 (5)	0.0164 (5)	−0.0007 (4)
O2	0.0534 (6)	0.0448 (6)	0.0349 (5)	0.0090 (5)	0.0155 (5)	0.0055 (4)
O1W	0.0697 (8)	0.0430 (7)	0.0384 (6)	0.0116 (6)	0.0019 (6)	−0.0018 (5)

Geometric parameters (Å, º) top

C1—O1	1.3644 (16)	C7—H7	0.9300
C1—C6	1.3864 (19)	C8—O2	1.2421 (17)
C1—C2	1.3941 (19)	C8—O2	1.2421 (17)
C2—C3	1.377 (2)	C8—N2	1.3346 (18)
C2—H2	0.9300	C8—C9	1.4988 (19)
C3—C4	1.4009 (19)	C9—H9A	0.9600
C3—H3	0.9300	C9—H9B	0.9600
C4—C5	1.3962 (19)	C9—H9C	0.9600
C4—C7	1.4611 (19)	N1—N2	1.3832 (16)
C5—C6	1.380 (2)	N2—H2A	0.8600
C5—H5	0.9300	O1—H1	0.8200
C6—H6	0.9300	O1W—H1E	0.85 (2)
C7—N1	1.2782 (18)	O1W—H1F	0.88 (2)

O1—C1—C6	118.28 (12)	N1—C7—H7	119.1
O1—C1—C2	121.98 (12)	C4—C7—H7	119.1
C6—C1—C2	119.74 (12)	O2—C8—N2	122.15 (12)
C3—C2—C1	120.12 (12)	O2—C8—N2	122.15 (12)
C3—C2—H2	119.9	O2—C8—C9	121.90 (13)
C1—C2—H2	119.9	O2—C8—C9	121.90 (13)
C2—C3—C4	120.85 (13)	N2—C8—C9	115.95 (12)
C2—C3—H3	119.6	C8—C9—H9A	109.5
C4—C3—H3	119.6	C8—C9—H9B	109.5
C5—C4—C3	118.15 (12)	H9A—C9—H9B	109.5
C5—C4—C7	119.94 (12)	C8—C9—H9C	109.5
C3—C4—C7	121.88 (12)	H9A—C9—H9C	109.5
C6—C5—C4	121.22 (12)	H9B—C9—H9C	109.5
C6—C5—H5	119.4	C7—N1—N2	115.36 (11)
C4—C5—H5	119.4	C8—N2—N1	119.60 (11)
C5—C6—C1	119.90 (13)	C8—N2—H2A	120.2
C5—C6—H6	120.1	N1—N2—H2A	120.2
C1—C6—H6	120.1	C1—O1—H1	109.5
N1—C7—C4	121.72 (12)	H1E—O1W—H1F	107 (2)

O1—C1—C2—C3	−177.94 (13)	C2—C1—C6—C5	−1.7 (2)
C6—C1—C2—C3	1.5 (2)	C5—C4—C7—N1	−179.03 (12)
C1—C2—C3—C4	−0.2 (2)	C3—C4—C7—N1	3.0 (2)
C2—C3—C4—C5	−0.8 (2)	C4—C7—N1—N2	−177.28 (11)
C2—C3—C4—C7	177.21 (13)	O2—C8—N2—N1	1.12 (19)
C3—C4—C5—C6	0.6 (2)	O2—C8—N2—N1	1.12 (19)
C7—C4—C5—C6	−177.44 (12)	C9—C8—N2—N1	−178.27 (11)
C4—C5—C6—C1	0.6 (2)	C7—N1—N2—C8	179.57 (12)
O1—C1—C6—C5	177.77 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	2.00	2.7477 (15)	152
N2—H2A···O1Wⁱⁱ	0.86	1.96	2.8060 (17)	166
O1W—H1F···O2	0.88 (2)	1.92 (2)	2.7600 (17)	159 (2)
O1W—H1E···O1ⁱⁱⁱ	0.85 (2)	2.01 (2)	2.8241 (17)	161 (2)
O1—H1···N1ⁱ	0.82	2.54	3.1864 (16)	137
C9—H9B···Cg1^iv	0.96	2.74	3.519 (2)	138

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

Experimental details

Crystal data
Chemical formula	C₉H₁₀N₂O₂·H₂O
M_r	196.21
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	223
a, b, c (Å)	8.352 (2), 10.146 (3), 12.328 (3)
β (°)	105.353 (3)
V (Å³)	1007.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.23 × 0.21 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.969, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	4820, 1764, 1569
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.100, 1.06
No. of reflections	1764
No. of parameters	147
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.22

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	2.00	2.7477 (15)	151.5
N2—H2A···O1Wⁱⁱ	0.86	1.96	2.8060 (17)	166.3
O1W—H1F···O2	0.88 (2)	1.92 (2)	2.7600 (17)	159 (2)
O1W—H1E···O1ⁱⁱⁱ	0.85 (2)	2.01 (2)	2.8241 (17)	161 (2)
O1—H1···N1ⁱ	0.82	2.54	3.1864 (16)	136.5
C9—H9B···Cg1^iv	0.96	2.74	3.519 (2)	138.00

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

Acknowledgements

The authors thank the Science and Technology Project of Zhejiang Province (grant No. 2007 F70077) for financial support.

References

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