4-Chloro-N′-(2-hydroxy­benzyl­idene)benzohydrazide monohydrate

Lu, J.-F.; Min, S.-T.; Ji, X.-H.; Dang, Z.-H.

doi:10.1107/S1600536808024471

organic compounds

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Volume 64| Part 9| September 2008| Page o1694

doi:10.1107/S1600536808024471

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4-Chloro-N′-(2-hydroxybenzylidene)benzohydrazide monohydrate

Jiu-Fu Lu,^a ^* Suo-Tian Min,^a Xiao-Hui Ji ^a and Zhong-Hai Dang ^a

^aSchool of Chemistry and Environmental Science, Shaanxi University of Technology, Hanzhong 723000, People's Republic of China
^*Correspondence e-mail: jiufulu@163.com

(Received 28 July 2008; accepted 31 July 2008; online 6 August 2008)

The asymmetric unit of the title compound, C₁₄H₁₁ClN₂O₂·H₂O, contains a Schiff base molecule and a water molecule of crystallization. The dihedral angle between the two aromatic rings is 27.3 (4)°. In the crystal structure, molecules are linked into a two-dimensional network parallel to the bc plane by intermolecular O—H⋯O and N—H⋯O hydrogen bonds involving the water molecules.

Related literature

For general background on Schiff bases derived from condensation of aldehydes with benzohydrazides, see: Fun et al. (2008 ); Alhadi et al. (2008 ); Ali et al. (2007 ); Zou et al. (2004 ); Shan et al. (2008 ); Bedia et al. (2006 ); Terzioglu & Gürsoy (2003 ). For related structures, see: Nie (2008 ); He (2008 ); Shi et al. (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₁ClN₂O₂·H₂O
M_r = 292.71
Monoclinic, P 2₁ /c
a = 22.397 (3) Å
b = 4.853 (2) Å
c = 12.642 (3) Å
β = 97.15 (3)°
V = 1363.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 298 (2) K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.937, T_max = 0.945
10537 measured reflections
2946 independent reflections
1251 reflections with I > 2σ(I)
R_int = 0.106

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.214
S = 0.99
2946 reflections
191 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2	0.84 (3)	1.97 (3)	2.800 (4)	170 (5)
O3—H3B⋯O2ⁱ	0.85 (3)	2.07 (3)	2.828 (4)	149 (5)
N2—H2⋯O3ⁱⁱ	0.90 (1)	1.96 (1)	2.856 (4)	172 (5)
O1—H1⋯N1	0.82	1.96	2.667 (5)	143
Symmetry codes: (i) x, y-1, z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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 global, I. DOI: 10.1107/S1600536808024471/ci2647sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808024471/ci2647Isup2.hkl

checkCIF report

Comment top

Schiff bases derived from the condensation of aldehydes with benzohydrazides have been widely investigated, either for their structures (Fun et al., 2008; Alhadi et al., 2008; Ali et al., 2007; Zou et al., 2004; Shan et al., 2008) or for their biological properties (Bedia et al., 2006; Terzioglu & Gürsoy, 2003). This study extends the structural study on such compounds.

The asymmetric unit of the title compound consists of a Schiff base molecule and a water molecule of crystallization (Fig. 1). The bond lengths are within normal values (Allen et al., 1987), and comparable to the values observed in related compounds (Nie, 2008; He, 2008; Shi et al., 2007). The dihedral angle between the two aromatic rings in the Schiff base molecule is 27.3 (4)°. An intramolecular O—H···N hydrogen bond is observed.

In the crystal structure, the molecules are linked into a two-dimensional network parallel to the bc plane by intermolecular O–H···O and N–H···O hydrogen bonds (Table 1) involving the water molecules (Fig. 2).

Related literature top

For general background on Schiff bases derived from condensation of aldehydes with benzohydrazides, see: Fun et al. (2008); Alhadi et al. (2008); Ali et al. (2007); Zou et al. (2004); Shan et al. (2008); Bedia et al. (2006); Terzioglu & Gürsoy (2003). For related structures, see: Nie (2008); He (2008); Shi et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the Schiff base condensation of salicylaldehyde (0.1 mol) and 4-chlorobenzohydrazide (0.1 mmol) in ethanol (50 ml). The excess ethanol was removed by distillation. The colourless solid formed was filtered and washed with ethanol. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Dashed lines indicate hydrogen bonds.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines.

4-Chloro-N'-(2-hydroxybenzylidene)benzohydrazide monohydrate top

Crystal data top

C₁₄H₁₁ClN₂O₂·H₂O	F(000) = 608
M_r = 292.71	D_x = 1.426 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 600 reflections
a = 22.397 (3) Å	θ = 2.6–24.5°
b = 4.853 (2) Å	µ = 0.29 mm⁻¹
c = 12.642 (3) Å	T = 298 K
β = 97.15 (3)°	Block, colourless
V = 1363.4 (7) Å³	0.23 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	2946 independent reflections
Radiation source: fine-focus sealed tube	1251 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.106
ω scans	θ_max = 27.0°, θ_min = 0.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −28→28
T_min = 0.937, T_max = 0.945	k = −6→6
10537 measured reflections	l = −15→15

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.214	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0902P)²] where P = (F_o² + 2F_c²)/3
2946 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.27 e Å⁻³
4 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₄H₁₁ClN₂O₂·H₂O	V = 1363.4 (7) Å³
M_r = 292.71	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 22.397 (3) Å	µ = 0.29 mm⁻¹
b = 4.853 (2) Å	T = 298 K
c = 12.642 (3) Å	0.23 × 0.20 × 0.20 mm
β = 97.15 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2946 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1251 reflections with I > 2σ(I)
T_min = 0.937, T_max = 0.945	R_int = 0.106
10537 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	4 restraints
wR(F²) = 0.214	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.27 e Å⁻³
2946 reflections	Δρ_min = −0.27 e Å⁻³
191 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
Cl1	0.02717 (6)	1.4002 (3)	0.66329 (12)	0.0731 (5)
N2	0.24096 (15)	0.4463 (8)	0.6210 (3)	0.0392 (9)
C8	0.21035 (19)	0.5999 (9)	0.5457 (3)	0.0412 (11)
N1	0.28603 (15)	0.2706 (7)	0.5952 (3)	0.0420 (10)
O2	0.21956 (14)	0.5852 (6)	0.4508 (2)	0.0538 (9)
C9	0.16460 (18)	0.7918 (8)	0.5783 (3)	0.0365 (10)
C14	0.16219 (18)	0.8667 (9)	0.6822 (3)	0.0426 (12)
H14	0.1893	0.7895	0.7359	0.051*
C1	0.35917 (19)	−0.0643 (9)	0.6600 (3)	0.0415 (11)
C7	0.31165 (18)	0.1242 (9)	0.6720 (3)	0.0428 (12)
H7	0.2987	0.1416	0.7388	0.051*
O1	0.36902 (17)	0.0745 (9)	0.4810 (3)	0.0779 (12)
H1	0.3447	0.1897	0.4963	0.117*
C11	0.0808 (2)	1.0889 (10)	0.5252 (4)	0.0537 (13)
H11	0.0531	1.1631	0.4720	0.064*
C12	0.07965 (19)	1.1639 (9)	0.6292 (4)	0.0457 (12)
C13	0.1200 (2)	1.0561 (10)	0.7088 (4)	0.0512 (13)
H13	0.1191	1.1086	0.7793	0.061*
C2	0.3871 (2)	−0.0802 (11)	0.5669 (4)	0.0536 (13)
C10	0.12292 (19)	0.9047 (10)	0.4998 (3)	0.0466 (12)
H10	0.1236	0.8543	0.4290	0.056*
C6	0.3802 (2)	−0.2325 (10)	0.7435 (4)	0.0577 (14)
H6	0.3624	−0.2236	0.8060	0.069*
C4	0.4539 (2)	−0.4315 (13)	0.6486 (5)	0.0726 (17)
H4	0.4851	−0.5558	0.6443	0.087*
C5	0.4271 (2)	−0.4144 (11)	0.7380 (5)	0.0656 (15)
H5	0.4402	−0.5255	0.7962	0.079*
C3	0.4344 (2)	−0.2616 (12)	0.5632 (5)	0.0739 (17)
H3	0.4536	−0.2697	0.5021	0.089*
O3	0.23525 (17)	0.0885 (7)	0.3450 (2)	0.0568 (9)
H2	0.236 (2)	0.445 (11)	0.6905 (12)	0.080*
H3B	0.245 (2)	−0.049 (5)	0.385 (3)	0.080*
H3A	0.235 (2)	0.234 (5)	0.381 (3)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0598 (8)	0.0587 (9)	0.1059 (12)	0.0176 (7)	0.0301 (8)	0.0051 (9)
N2	0.042 (2)	0.044 (2)	0.0329 (19)	0.0072 (18)	0.0065 (17)	0.002 (2)
C8	0.044 (3)	0.040 (3)	0.039 (3)	0.000 (2)	0.003 (2)	0.004 (2)
N1	0.041 (2)	0.042 (2)	0.044 (2)	0.0057 (19)	0.0121 (18)	−0.006 (2)
O2	0.078 (2)	0.050 (2)	0.0345 (18)	0.0109 (18)	0.0142 (16)	0.0034 (16)
C9	0.038 (2)	0.030 (3)	0.041 (3)	−0.002 (2)	0.005 (2)	0.003 (2)
C14	0.045 (3)	0.046 (3)	0.035 (3)	0.005 (2)	−0.001 (2)	0.004 (2)
C1	0.037 (2)	0.038 (3)	0.049 (3)	−0.001 (2)	0.003 (2)	−0.007 (2)
C7	0.044 (3)	0.052 (3)	0.033 (2)	0.005 (2)	0.005 (2)	−0.001 (2)
O1	0.084 (3)	0.098 (3)	0.054 (2)	0.030 (2)	0.0195 (19)	0.002 (2)
C11	0.050 (3)	0.058 (3)	0.053 (3)	0.001 (3)	0.001 (2)	0.005 (3)
C12	0.040 (2)	0.033 (3)	0.065 (3)	0.004 (2)	0.010 (2)	0.007 (2)
C13	0.053 (3)	0.051 (3)	0.050 (3)	0.006 (3)	0.010 (2)	−0.001 (3)
C2	0.051 (3)	0.061 (4)	0.048 (3)	0.009 (3)	0.004 (2)	−0.005 (3)
C10	0.044 (3)	0.054 (3)	0.041 (3)	0.007 (3)	0.003 (2)	0.004 (3)
C6	0.050 (3)	0.055 (3)	0.066 (3)	0.003 (3)	−0.002 (3)	−0.005 (3)
C4	0.051 (3)	0.068 (4)	0.096 (5)	0.019 (3)	−0.001 (3)	−0.024 (4)
C5	0.063 (4)	0.050 (4)	0.077 (4)	−0.001 (3)	−0.019 (3)	−0.002 (3)
C3	0.064 (4)	0.078 (4)	0.083 (4)	0.017 (3)	0.020 (3)	−0.025 (4)
O3	0.091 (2)	0.047 (2)	0.0328 (17)	−0.007 (2)	0.0107 (17)	−0.0014 (17)

Geometric parameters (Å, º) top

Cl1—C12	1.735 (4)	C11—C10	1.366 (6)
N2—C8	1.330 (5)	C11—C12	1.367 (6)
N2—N1	1.391 (5)	C11—H11	0.93
N2—H2	0.899 (10)	C12—C13	1.370 (6)
C8—O2	1.245 (5)	C13—H13	0.93
C8—C9	1.481 (6)	C2—C3	1.384 (7)
N1—C7	1.280 (5)	C10—H10	0.93
C9—C14	1.370 (6)	C6—C5	1.380 (7)
C9—C10	1.388 (6)	C6—H6	0.93
C14—C13	1.390 (6)	C4—C5	1.346 (7)
C14—H14	0.93	C4—C3	1.386 (7)
C1—C6	1.371 (6)	C4—H4	0.93
C1—C2	1.401 (6)	C5—H5	0.93
C1—C7	1.426 (6)	C3—H3	0.93
C7—H7	0.93	O3—H3B	0.85 (3)
O1—C2	1.340 (5)	O3—H3A	0.84 (3)
O1—H1	0.82

C8—N2—N1	120.0 (3)	C11—C12—Cl1	120.7 (4)
C8—N2—H2	126 (3)	C13—C12—Cl1	118.3 (4)
N1—N2—H2	114 (3)	C12—C13—C14	118.8 (4)
O2—C8—N2	121.7 (4)	C12—C13—H13	120.6
O2—C8—C9	120.5 (4)	C14—C13—H13	120.6
N2—C8—C9	117.8 (4)	O1—C2—C3	119.0 (5)
C7—N1—N2	115.6 (3)	O1—C2—C1	121.9 (4)
C14—C9—C10	118.5 (4)	C3—C2—C1	119.1 (5)
C14—C9—C8	123.0 (4)	C11—C10—C9	120.8 (4)
C10—C9—C8	118.4 (4)	C11—C10—H10	119.6
C9—C14—C13	121.1 (4)	C9—C10—H10	119.6
C9—C14—H14	119.5	C1—C6—C5	122.2 (5)
C13—C14—H14	119.5	C1—C6—H6	118.9
C6—C1—C2	117.9 (4)	C5—C6—H6	118.9
C6—C1—C7	119.3 (4)	C5—C4—C3	119.1 (5)
C2—C1—C7	122.8 (4)	C5—C4—H4	120.4
N1—C7—C1	123.0 (4)	C3—C4—H4	120.4
N1—C7—H7	118.5	C4—C5—C6	120.3 (5)
C1—C7—H7	118.5	C4—C5—H5	119.9
C2—O1—H1	109.5	C6—C5—H5	119.9
C10—C11—C12	119.8 (4)	C2—C3—C4	121.4 (5)
C10—C11—H11	120.1	C2—C3—H3	119.3
C12—C11—H11	120.1	C4—C3—H3	119.3
C11—C12—C13	121.0 (4)	H3B—O3—H3A	111 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.84 (3)	1.97 (3)	2.800 (4)	170 (5)
O3—H3B···O2ⁱ	0.85 (3)	2.07 (3)	2.828 (4)	149 (5)
N2—H2···O3ⁱⁱ	0.90 (1)	1.96 (1)	2.856 (4)	172 (5)
O1—H1···N1	0.82	1.96	2.667 (5)	143

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁ClN₂O₂·H₂O
M_r	292.71
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	22.397 (3), 4.853 (2), 12.642 (3)
β (°)	97.15 (3)
V (Å³)	1363.4 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.937, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	10537, 2946, 1251
R_int	0.106
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.214, 0.99
No. of reflections	2946
No. of parameters	191
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.27

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), 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
O3—H3A···O2	0.84 (3)	1.97 (3)	2.800 (4)	170 (5)
O3—H3B···O2ⁱ	0.85 (3)	2.07 (3)	2.828 (4)	149 (5)
N2—H2···O3ⁱⁱ	0.90 (1)	1.96 (1)	2.856 (4)	172 (5)
O1—H1···N1	0.82	1.96	2.667 (5)	143

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

Acknowledgements

The authors acknowledge Shaanxi University of Technology for the research fund.

References

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