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

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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.069
• wR factor = 0.215
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.106
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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).

S2. Experimental

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.

S3. Refinement

The imino and water H atoms were located in a difference map and refined with N–H, O–H and H···H distances restrained to 0.90 (1), 0.85 (1), and 1.37 (2)Å, respectively. The other H atoms were positioned geometrically [C–H = 0.93 Å and O–H = 0.82Å] and refined using a riding model, with U_iso(H) = 1.2U_eq(C) and 1.5U_eq(O1).

Computing details

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

	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

Crystal data

C14H11ClN2O2·H2O	F(000) = 608
Mr = 292.71	Dx = 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) Å^3	0.23 × 0.20 × 0.20 mm
Z = 4

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.214	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0902P)^2] where P = (Fo^2 + 2Fc^2)/3
2946 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.27 e Å^−3
4 restraints	Δρmin = −0.27 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O2^i	0.85 (3)	2.07 (3)	2.828 (4)	149 (5)
N2—H2···O3^ii	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.