(E)-N′-(2-Chloro­benzyl­idene)-3,5-di­hydroxy­benzohydrazide dihydrate

Yuan, L.; Nan, Y.; Li, J.-Y.; Huang, X.-L.

doi:10.1107/S1600536811042681

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3017

doi:10.1107/S1600536811042681

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(E)-N′-(2-Chlorobenzylidene)-3,5-dihydroxybenzohydrazide dihydrate

Ling Yuan,^a,^c Yi Nan,^b Jing-Yuan Li ^c and Xiu-Lan Huang ^c ^*

^aPharmacy College of Ningxia Medical University, Yinchuan, Ningxia Province 750004, People's Republic of China, ^bTraditional Chinese Medicine College of Ningxia Medical University, Ningxia Province, 750004, People's Republic of China, and ^cMinority Traditional Medical Center of Minzu University of China, Beijing 100081, People's Republic of China
^*Correspondence e-mail: Nanyiailing10@126.com

(Received 10 October 2011; accepted 14 October 2011; online 22 October 2011)

In the Schiff base molecule of the title compound, C₁₄H₁₁ClN₂O₃·2H₂O, the benzene rings form a dihedral angle of 20.6 (1)°. The water molecules of crystallization are involved in the formation of a three-dimensional hydrogen-bonding network via O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For general background to Schiff base compounds, see: Brückner et al. (2000 ); Harrop et al.(2003 ); Zhang et al. (2008 ). For related structures, see: Diao et al. (2007 ); Jiang et al. (2008 ); Huang et al. (2008 ); Deng et al. (2009 ).

Experimental

Crystal data

C₁₄H₁₁ClN₂O₃·2H₂O
M_r = 326.73
Monoclinic, P 2₁ /c
a = 8.023 (2) Å
b = 11.852 (4) Å
c = 16.318 (5) Å
β = 100.387 (4)°
V = 1526.1 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 296 K
0.44 × 0.12 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer
12729 measured reflections
3522 independent reflections
2286 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.140
S = 1.03
3522 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯O5	0.82	1.87	2.674 (3)	168
O3—H3A⋯O1ⁱ	0.82	1.85	2.665 (2)	169
N2—H2A⋯O2ⁱⁱ	0.86	2.36	3.196 (3)	164
O4—H4B⋯O1	0.85	2.12	2.960 (4)	171
O5—H5A⋯O4ⁱⁱⁱ	0.85	1.99	2.816 (4)	163
O5—H5B⋯O3^iv	0.85	2.14	2.902 (3)	150
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x+1, y, z; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811042681/cv5172sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811042681/cv5172Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811042681/cv5172Isup3.cml

checkCIF report

Comment top

Schiff base compounds are known to exhibit antibacterial and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Zhang et al., 2008). In order to expand this filed, we report here the structure of the title compound (I).

In (I) (Fig. 1), all bond lengths and angles are normal and comparable with those found in the related compounds (Diao et al., 2007; Deng et al., 2009; Huang et al., 2008, Jiang et al., 2008). In the Shiff base molecule, two benzene rings form a dihedral angle of 20.6 (1)°.

In the crystal structure, intermolecular O—H···O and N—H···O hydrogen bonds (Table 1) consolidate the crystal packing.

Related literature top

For general background to Schiff base compounds, see: Brückner et al. (2000); Harrop et al.(2003); Zhang et al. (2008). For related structures, see: Diao et al. (2007); Jiang et al. (2008); Huang et al. (2008); Deng et al. (2009).

Experimental top

2-Chlorobenzaldehyde (0.1 mmol, 14.1 mg) and 3,5-dihydroxybenzhydrazide (0.1 mmol, 16.8 mg) were dissolved in a methanol solution (10 ml). The mixture was stirred at room temperature for 1 h and filtered. After keeping the filtrate in air for three days, yellow crystals were formed.

Computing details top

Data collection: SMART [or APEX2?] (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing the atomic numbering and 30% probability displacement ellipsoids.

(E)-N'-(2-Chlorobenzylidene)-3,5-dihydroxybenzohydrazide dihydrate top

Crystal data top

C₁₄H₁₁ClN₂O₃·2H₂O	F(000) = 680
M_r = 326.73	D_x = 1.422 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 4061 reflections
a = 8.023 (2) Å	θ = 2.5–27.1°
b = 11.852 (4) Å	µ = 0.28 mm⁻¹
c = 16.318 (5) Å	T = 296 K
β = 100.387 (4)°	Stick, yellow
V = 1526.1 (8) Å³	0.44 × 0.12 × 0.07 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2286 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.040
Graphite monochromator	θ_max = 27.6°, θ_min = 2.1°
ϕ and ω scans	h = −10→10
12729 measured reflections	k = −15→15
3522 independent reflections	l = −20→21

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.044P)² + 1.2P] where P = (F_o² + 2F_c²)/3
3522 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₄H₁₁ClN₂O₃·2H₂O	V = 1526.1 (8) Å³
M_r = 326.73	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.023 (2) Å	µ = 0.28 mm⁻¹
b = 11.852 (4) Å	T = 296 K
c = 16.318 (5) Å	0.44 × 0.12 × 0.07 mm
β = 100.387 (4)°

Data collection top

Bruker APEXII CCD diffractometer	2286 reflections with I > 2σ(I)
12729 measured reflections	R_int = 0.040
3522 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.03	Δρ_max = 0.32 e Å⁻³
3522 reflections	Δρ_min = −0.33 e Å⁻³
199 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
Cl1	0.07549 (13)	0.73732 (7)	0.46696 (6)	0.0836 (3)
O1	0.4482 (3)	0.20583 (16)	0.45642 (10)	0.0555 (5)
O2	0.7564 (2)	0.07180 (15)	0.22642 (10)	0.0508 (5)
H2B	0.7932	0.0426	0.2716	0.076*
O3	0.3480 (3)	0.33745 (18)	0.10033 (10)	0.0615 (6)
H3A	0.3864	0.3177	0.0593	0.092*
N1	0.3161 (2)	0.41028 (17)	0.48357 (10)	0.0374 (4)
N2	0.3589 (2)	0.37857 (17)	0.40850 (10)	0.0368 (4)
H2A	0.3450	0.4252	0.3674	0.044*
C1	0.1081 (3)	0.6554 (2)	0.55602 (17)	0.0472 (6)
C2	0.0554 (4)	0.6968 (3)	0.6271 (2)	0.0621 (8)
H2	0.0022	0.7666	0.6257	0.074*
C3	0.0818 (4)	0.6351 (3)	0.6986 (2)	0.0678 (9)
H3	0.0483	0.6635	0.7462	0.081*
C4	0.1571 (4)	0.5318 (3)	0.70062 (18)	0.0687 (9)
H4	0.1738	0.4897	0.7495	0.082*
C5	0.2090 (4)	0.4891 (3)	0.63044 (16)	0.0550 (7)
H5	0.2596	0.4184	0.6326	0.066*
C6	0.1866 (3)	0.5505 (2)	0.55659 (14)	0.0382 (5)
C7	0.2396 (3)	0.5047 (2)	0.48164 (14)	0.0371 (5)
H7	0.2171	0.5453	0.4321	0.044*
C8	0.4220 (3)	0.2757 (2)	0.39941 (12)	0.0353 (5)
C9	0.4635 (3)	0.25014 (19)	0.31552 (12)	0.0326 (5)
C10	0.5859 (3)	0.16929 (19)	0.31167 (12)	0.0347 (5)
H10	0.6357	0.1302	0.3592	0.042*
C11	0.6334 (3)	0.14750 (19)	0.23525 (13)	0.0351 (5)
C12	0.5573 (3)	0.2046 (2)	0.16457 (12)	0.0387 (5)
H12	0.5916	0.1910	0.1140	0.046*
C13	0.4305 (3)	0.2818 (2)	0.16880 (12)	0.0387 (5)
C14	0.3828 (3)	0.3059 (2)	0.24457 (13)	0.0393 (5)
H14	0.2981	0.3585	0.2477	0.047*
O4	0.2697 (4)	−0.0135 (3)	0.4316 (2)	0.1159 (11)
H4A	0.3177	−0.0688	0.4595	0.174*
H4B	0.3266	0.0473	0.4339	0.174*
O5	0.9176 (3)	−0.00817 (18)	0.37266 (13)	0.0690 (6)
H5A	1.0182	−0.0070	0.4001	0.104*
H5B	0.8554	−0.0465	0.3993	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1051 (7)	0.0521 (5)	0.0969 (7)	0.0157 (5)	0.0274 (6)	0.0134 (4)
O1	0.0881 (14)	0.0572 (11)	0.0272 (8)	0.0154 (10)	0.0261 (9)	0.0084 (8)
O2	0.0624 (12)	0.0562 (11)	0.0360 (9)	0.0213 (9)	0.0146 (8)	−0.0016 (8)
O3	0.0820 (14)	0.0817 (14)	0.0224 (8)	0.0345 (12)	0.0139 (8)	0.0076 (8)
N1	0.0404 (11)	0.0505 (12)	0.0244 (8)	0.0010 (9)	0.0141 (8)	−0.0046 (8)
N2	0.0438 (11)	0.0479 (11)	0.0217 (8)	0.0006 (9)	0.0140 (8)	−0.0011 (8)
C1	0.0379 (14)	0.0438 (14)	0.0619 (16)	−0.0085 (11)	0.0146 (12)	−0.0153 (12)
C2	0.0455 (16)	0.0534 (17)	0.093 (2)	−0.0089 (13)	0.0284 (16)	−0.0352 (17)
C3	0.0585 (19)	0.087 (2)	0.067 (2)	−0.0154 (17)	0.0349 (16)	−0.0362 (18)
C4	0.071 (2)	0.097 (3)	0.0449 (15)	0.0004 (19)	0.0279 (14)	−0.0074 (16)
C5	0.0568 (17)	0.0714 (19)	0.0414 (14)	0.0092 (14)	0.0212 (12)	−0.0046 (13)
C6	0.0311 (12)	0.0477 (13)	0.0384 (12)	−0.0053 (10)	0.0131 (9)	−0.0095 (10)
C7	0.0366 (12)	0.0455 (13)	0.0311 (11)	−0.0054 (11)	0.0114 (9)	−0.0022 (9)
C8	0.0394 (12)	0.0451 (13)	0.0240 (10)	0.0002 (10)	0.0129 (9)	−0.0016 (9)
C9	0.0368 (12)	0.0419 (12)	0.0209 (9)	−0.0035 (10)	0.0103 (8)	−0.0017 (8)
C10	0.0403 (13)	0.0412 (12)	0.0235 (9)	0.0004 (10)	0.0081 (9)	0.0006 (9)
C11	0.0406 (13)	0.0376 (12)	0.0290 (10)	−0.0009 (10)	0.0112 (9)	−0.0055 (9)
C12	0.0497 (14)	0.0474 (13)	0.0220 (9)	0.0015 (11)	0.0146 (9)	−0.0062 (9)
C13	0.0464 (13)	0.0481 (13)	0.0222 (10)	0.0042 (11)	0.0076 (9)	0.0001 (9)
C14	0.0464 (14)	0.0480 (13)	0.0257 (10)	0.0100 (11)	0.0124 (9)	−0.0005 (9)
O4	0.099 (2)	0.098 (2)	0.138 (3)	−0.0265 (18)	−0.0111 (19)	0.0009 (19)
O5	0.0685 (14)	0.0749 (14)	0.0616 (12)	0.0020 (11)	0.0063 (10)	0.0216 (11)

Geometric parameters (Å, º) top

Cl1—C1	1.728 (3)	C5—C6	1.391 (4)
O1—C8	1.235 (3)	C5—H5	0.9300
O2—C11	1.361 (3)	C6—C7	1.469 (3)
O2—H2B	0.8200	C7—H7	0.9300
O3—C13	1.362 (3)	C8—C9	1.497 (3)
O3—H3A	0.8200	C9—C10	1.382 (3)
N1—C7	1.274 (3)	C9—C14	1.388 (3)
N1—N2	1.383 (2)	C10—C11	1.392 (3)
N2—C8	1.338 (3)	C10—H10	0.9300
N2—H2A	0.8600	C11—C12	1.381 (3)
C1—C6	1.392 (4)	C12—C13	1.379 (3)
C1—C2	1.393 (4)	C12—H12	0.9300
C2—C3	1.361 (5)	C13—C14	1.388 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.363 (5)	O4—H4A	0.8500
C3—H3	0.9300	O4—H4B	0.8500
C4—C5	1.383 (4)	O5—H5A	0.8500
C4—H4	0.9300	O5—H5B	0.8500

C11—O2—H2B	109.5	N1—C7—H7	119.5
C13—O3—H3A	109.5	C6—C7—H7	119.5
C7—N1—N2	114.36 (19)	O1—C8—N2	122.96 (18)
C8—N2—N1	120.34 (18)	O1—C8—C9	121.1 (2)
C8—N2—H2A	119.8	N2—C8—C9	115.90 (19)
N1—N2—H2A	119.8	C10—C9—C14	121.39 (18)
C6—C1—C2	120.9 (3)	C10—C9—C8	117.35 (19)
C6—C1—Cl1	120.46 (19)	C14—C9—C8	121.3 (2)
C2—C1—Cl1	118.6 (2)	C9—C10—C11	118.7 (2)
C3—C2—C1	120.1 (3)	C9—C10—H10	120.6
C3—C2—H2	120.0	C11—C10—H10	120.6
C1—C2—H2	120.0	O2—C11—C12	117.05 (18)
C2—C3—C4	120.2 (3)	O2—C11—C10	122.6 (2)
C2—C3—H3	119.9	C12—C11—C10	120.4 (2)
C4—C3—H3	119.9	C13—C12—C11	120.16 (18)
C3—C4—C5	120.4 (3)	C13—C12—H12	119.9
C3—C4—H4	119.8	C11—C12—H12	119.9
C5—C4—H4	119.8	O3—C13—C12	122.25 (18)
C4—C5—C6	121.0 (3)	O3—C13—C14	117.4 (2)
C4—C5—H5	119.5	C12—C13—C14	120.3 (2)
C6—C5—H5	119.5	C9—C14—C13	118.9 (2)
C5—C6—C1	117.4 (2)	C9—C14—H14	120.6
C5—C6—C7	121.1 (2)	C13—C14—H14	120.6
C1—C6—C7	121.5 (2)	H4A—O4—H4B	116.3
N1—C7—C6	120.9 (2)	H5A—O5—H5B	109.2

C7—N1—N2—C8	−172.3 (2)	O1—C8—C9—C10	−24.0 (3)
C6—C1—C2—C3	0.6 (4)	N2—C8—C9—C10	154.7 (2)
Cl1—C1—C2—C3	−178.9 (2)	O1—C8—C9—C14	156.3 (2)
C1—C2—C3—C4	−1.1 (5)	N2—C8—C9—C14	−25.0 (3)
C2—C3—C4—C5	0.6 (5)	C14—C9—C10—C11	2.8 (3)
C3—C4—C5—C6	0.4 (5)	C8—C9—C10—C11	−176.9 (2)
C4—C5—C6—C1	−0.9 (4)	C9—C10—C11—O2	178.0 (2)
C4—C5—C6—C7	−179.2 (3)	C9—C10—C11—C12	−1.0 (3)
C2—C1—C6—C5	0.4 (4)	O2—C11—C12—C13	179.4 (2)
Cl1—C1—C6—C5	179.9 (2)	C10—C11—C12—C13	−1.6 (4)
C2—C1—C6—C7	178.7 (2)	C11—C12—C13—O3	−177.8 (2)
Cl1—C1—C6—C7	−1.7 (3)	C11—C12—C13—C14	2.4 (4)
N2—N1—C7—C6	−179.62 (19)	C10—C9—C14—C13	−2.0 (4)
C5—C6—C7—N1	−3.9 (4)	C8—C9—C14—C13	177.7 (2)
C1—C6—C7—N1	177.8 (2)	O3—C13—C14—C9	179.6 (2)
N1—N2—C8—O1	−1.5 (4)	C12—C13—C14—C9	−0.6 (4)
N1—N2—C8—C9	179.82 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O5	0.82	1.87	2.674 (3)	168
O3—H3A···O1ⁱ	0.82	1.85	2.665 (2)	169
N2—H2A···O2ⁱⁱ	0.86	2.36	3.196 (3)	164
O4—H4B···O1	0.85	2.12	2.960 (4)	171
O5—H5A···O4ⁱⁱⁱ	0.85	1.99	2.816 (4)	163
O5—H5B···O3^iv	0.85	2.14	2.902 (3)	150

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁ClN₂O₃·2H₂O
M_r	326.73
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.023 (2), 11.852 (4), 16.318 (5)
β (°)	100.387 (4)
V (Å³)	1526.1 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.44 × 0.12 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12729, 3522, 2286
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.140, 1.03
No. of reflections	3522
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.33

Computer programs: SMART [or APEX2?] (Bruker, 2001), SAINT-Plus (Bruker, 2003), 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
O2—H2B···O5	0.82	1.87	2.674 (3)	168.2
O3—H3A···O1ⁱ	0.82	1.85	2.665 (2)	169.3
N2—H2A···O2ⁱⁱ	0.86	2.36	3.196 (3)	163.5
O4—H4B···O1	0.85	2.12	2.960 (4)	170.5
O5—H5A···O4ⁱⁱⁱ	0.85	1.99	2.816 (4)	163.2
O5—H5B···O3^iv	0.85	2.14	2.902 (3)	149.8

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

Acknowledgements

This project was supported by the National Natural Science Foundation of China (grant No. 81102893) and 2011 Ningxia Science and Technology Key Projects (grant No. 2011-25) and 2009 Ningxia Science and Technology Key Projects (grant No. 232).

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