4-Hydr-oxy-N'-(3,5-dichloro-2-hydroxy-benzyl-idene)benzohydrazide.

In the title compound, C(14)H(10)Cl(2)N(2)O(3), the dihedral angle between the two benzene rings is 5.1 (2)°. The mol-ecule adopts an E configuration with respect to the C=N bond and an intra-molecular O-H⋯N inter-action is present. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For the biological properties of Schiff base compounds, see: Jeewoth et al. (1999 ▶); Ren et al. (2002 ▶); Eltayeb et al. (2008 ▶); Sinha et al. (2008 ▶). For metal complexes of Schiff base compounds, see: Shivakumar et al. (2008 ▶); Prabhakaran et al. (2006 ▶); Dhar et al. (2005 ▶). For related structures, see: Cui et al. (2007 ▶); Jing et al. (2007 ▶); Ma et al. (2008 ▶); Salhin et al. (2007 ▶); Lin et al. (2007 ▶); Alhadi et al. (2008 ▶); Xue et al. (2008 ▶); Wang et al. (2008 ▶); Lu (2008 ▶); Diao et al. (2008 ▶); Qiu (2009 ▶); Mohd Lair et al. (2009a ▶,b ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H10Cl2N2O3

M = 325.14

Monoclinic,

a = 8.030 (1) Å

b = 13.546 (2) Å

c = 13.433 (2) Å

β = 107.247 (2)°

V = 1395.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.911, T max = 0.919

8463 measured reflections

3039 independent reflections

2324 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.107

S = 1.03

3039 reflections

195 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.36 e Å−3

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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020820/bx2214sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020820/bx2214Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H10Cl2N2O3	F(000) = 664
Mr = 325.14	Dx = 1.547 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2634 reflections
a = 8.030 (1) Å	θ = 2.2–26.0°
b = 13.546 (2) Å	µ = 0.48 mm−1
c = 13.433 (2) Å	T = 298 K
β = 107.247 (2)°	Block, yellow
V = 1395.5 (3) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3039 independent reflections
Radiation source: fine-focus sealed tube	2324 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.911, Tmax = 0.919	k = −17→17
8463 measured reflections	l = −17→14

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0503P)2 + 0.3954P] where P = (Fo2 + 2Fc2)/3
3039 reflections	(Δ/σ)max = 0.001
195 parameters	Δρmax = 0.22 e Å−3
1 restraint	Δρmin = −0.36 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	−0.05205 (8)	0.19042 (4)	1.13049 (5)	0.0682 (2)
Cl2	0.17799 (11)	0.43904 (5)	1.45283 (5)	0.0843 (2)
N1	0.25047 (18)	0.49746 (11)	1.00303 (11)	0.0382 (3)
N2	0.31078 (19)	0.56552 (10)	0.94624 (11)	0.0387 (3)
O1	0.08301 (19)	0.33479 (10)	1.01678 (10)	0.0512 (3)
H1	0.1314	0.3745	0.9885	0.077*
O2	0.26379 (19)	0.45814 (10)	0.81320 (10)	0.0540 (4)
O3	0.55673 (19)	0.80001 (10)	0.59831 (10)	0.0512 (3)
H3	0.6200	0.8433	0.6322	0.077*
C1	0.1834 (2)	0.45241 (12)	1.15726 (13)	0.0369 (4)
C2	0.1046 (2)	0.36288 (13)	1.11609 (14)	0.0384 (4)
C3	0.0458 (2)	0.30054 (13)	1.18096 (15)	0.0422 (4)
C4	0.0667 (2)	0.32330 (14)	1.28362 (15)	0.0467 (5)
H4	0.0275	0.2804	1.3259	0.056*
C5	0.1470 (3)	0.41115 (15)	1.32275 (14)	0.0479 (5)
C6	0.2037 (2)	0.47558 (14)	1.26095 (14)	0.0436 (4)
H6	0.2558	0.5348	1.2885	0.052*
C7	0.2478 (2)	0.52136 (13)	1.09426 (13)	0.0388 (4)
H7	0.2873	0.5833	1.1208	0.047*
C8	0.3119 (2)	0.54031 (13)	0.84892 (13)	0.0366 (4)
C9	0.3736 (2)	0.61545 (12)	0.78824 (13)	0.0354 (4)
C10	0.3425 (3)	0.59603 (15)	0.68236 (14)	0.0468 (4)
H10	0.2799	0.5400	0.6532	0.056*
C11	0.4035 (3)	0.65890 (16)	0.62059 (14)	0.0497 (5)
H11	0.3815	0.6454	0.5500	0.060*
C12	0.4974 (2)	0.74196 (13)	0.66340 (13)	0.0402 (4)
C13	0.5276 (2)	0.76339 (13)	0.76825 (13)	0.0404 (4)
H13	0.5893	0.8199	0.7969	0.049*
C14	0.4656 (2)	0.70024 (13)	0.82994 (13)	0.0383 (4)
H14	0.4856	0.7147	0.9002	0.046*
H2	0.352 (3)	0.6232 (11)	0.9766 (18)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0753 (4)	0.0500 (3)	0.0806 (4)	−0.0224 (3)	0.0252 (3)	−0.0019 (3)
Cl2	0.1359 (6)	0.0822 (5)	0.0491 (3)	−0.0081 (4)	0.0492 (4)	−0.0052 (3)
N1	0.0398 (8)	0.0373 (7)	0.0391 (8)	0.0010 (6)	0.0143 (6)	0.0045 (6)
N2	0.0462 (8)	0.0364 (8)	0.0361 (8)	−0.0036 (6)	0.0165 (7)	0.0022 (6)
O1	0.0629 (9)	0.0480 (8)	0.0433 (7)	−0.0110 (6)	0.0165 (6)	−0.0057 (6)
O2	0.0730 (10)	0.0428 (7)	0.0462 (8)	−0.0120 (7)	0.0174 (7)	−0.0068 (6)
O3	0.0679 (10)	0.0503 (8)	0.0392 (7)	0.0019 (6)	0.0218 (7)	0.0104 (6)
C1	0.0357 (9)	0.0358 (9)	0.0422 (9)	0.0033 (7)	0.0160 (7)	0.0027 (7)
C2	0.0340 (9)	0.0394 (9)	0.0421 (9)	0.0042 (7)	0.0117 (7)	0.0021 (7)
C3	0.0347 (9)	0.0383 (9)	0.0543 (11)	0.0006 (7)	0.0140 (8)	0.0040 (8)
C4	0.0438 (10)	0.0478 (11)	0.0553 (11)	0.0066 (8)	0.0249 (9)	0.0130 (9)
C5	0.0563 (12)	0.0525 (11)	0.0413 (10)	0.0068 (9)	0.0241 (9)	0.0032 (8)
C6	0.0500 (11)	0.0404 (9)	0.0452 (10)	0.0000 (8)	0.0212 (9)	−0.0030 (8)
C7	0.0399 (9)	0.0355 (9)	0.0427 (10)	−0.0012 (7)	0.0147 (8)	−0.0003 (7)
C8	0.0359 (9)	0.0382 (9)	0.0343 (9)	0.0031 (7)	0.0080 (7)	0.0008 (7)
C9	0.0345 (9)	0.0392 (9)	0.0326 (8)	0.0059 (7)	0.0102 (7)	0.0010 (7)
C10	0.0527 (11)	0.0510 (11)	0.0347 (9)	−0.0067 (9)	0.0098 (8)	−0.0043 (8)
C11	0.0588 (12)	0.0615 (12)	0.0276 (9)	−0.0009 (10)	0.0107 (8)	−0.0009 (8)
C12	0.0453 (10)	0.0419 (10)	0.0351 (9)	0.0116 (8)	0.0144 (7)	0.0106 (7)
C13	0.0468 (10)	0.0376 (9)	0.0373 (9)	0.0016 (8)	0.0132 (8)	0.0003 (7)
C14	0.0453 (10)	0.0412 (9)	0.0299 (8)	0.0037 (7)	0.0135 (7)	−0.0014 (7)

Cl1—C3	1.7281 (19)	C4—C5	1.381 (3)
Cl2—C5	1.7321 (19)	C4—H4	0.9300
N1—C7	1.274 (2)	C5—C6	1.372 (3)
N1—N2	1.3732 (19)	C6—H6	0.9300
N2—C8	1.354 (2)	C7—H7	0.9300
N2—H2	0.899 (10)	C8—C9	1.478 (2)
O1—C2	1.348 (2)	C9—C14	1.390 (2)
O1—H1	0.8200	C9—C10	1.394 (2)
O2—C8	1.228 (2)	C10—C11	1.376 (3)
O3—C12	1.363 (2)	C10—H10	0.9300
O3—H3	0.8200	C11—C12	1.381 (3)
C1—C6	1.389 (2)	C11—H11	0.9300
C1—C2	1.403 (2)	C12—C13	1.387 (2)
C1—C7	1.455 (2)	C13—C14	1.383 (2)
C2—C3	1.393 (2)	C13—H13	0.9300
C3—C4	1.374 (3)	C14—H14	0.9300
C7—N1—N2	118.23 (15)	N1—C7—C1	120.45 (16)
C8—N2—N1	118.12 (14)	N1—C7—H7	119.8
C8—N2—H2	123.3 (16)	C1—C7—H7	119.8
N1—N2—H2	118.5 (16)	O2—C8—N2	120.98 (16)
C2—O1—H1	109.5	O2—C8—C9	121.77 (15)
C12—O3—H3	109.5	N2—C8—C9	117.26 (15)
C6—C1—C2	119.72 (16)	C14—C9—C10	118.68 (16)
C6—C1—C7	118.80 (16)	C14—C9—C8	124.85 (15)
C2—C1—C7	121.47 (15)	C10—C9—C8	116.40 (16)
O1—C2—C3	118.68 (16)	C11—C10—C9	120.67 (18)
O1—C2—C1	123.01 (16)	C11—C10—H10	119.7
C3—C2—C1	118.30 (16)	C9—C10—H10	119.7
C4—C3—C2	121.93 (17)	C10—C11—C12	120.06 (16)
C4—C3—Cl1	119.57 (14)	C10—C11—H11	120.0
C2—C3—Cl1	118.49 (15)	C12—C11—H11	120.0
C3—C4—C5	118.66 (17)	O3—C12—C11	117.03 (15)
C3—C4—H4	120.7	O3—C12—C13	122.78 (17)
C5—C4—H4	120.7	C11—C12—C13	120.19 (16)
C6—C5—C4	121.27 (17)	C14—C13—C12	119.56 (17)
C6—C5—Cl2	119.84 (16)	C14—C13—H13	120.2
C4—C5—Cl2	118.89 (15)	C12—C13—H13	120.2
C5—C6—C1	120.10 (17)	C13—C14—C9	120.82 (15)
C5—C6—H6	120.0	C13—C14—H14	119.6
C1—C6—H6	120.0	C9—C14—H14	119.6
C7—N1—N2—C8	−179.36 (15)	C6—C1—C7—N1	171.54 (16)
C6—C1—C2—O1	−178.94 (16)	C2—C1—C7—N1	−7.3 (3)
C7—C1—C2—O1	−0.1 (3)	N1—N2—C8—O2	−1.5 (2)
C6—C1—C2—C3	1.3 (2)	N1—N2—C8—C9	178.67 (14)
C7—C1—C2—C3	−179.91 (16)	O2—C8—C9—C14	−164.75 (17)
O1—C2—C3—C4	178.59 (17)	N2—C8—C9—C14	15.1 (2)
C1—C2—C3—C4	−1.6 (3)	O2—C8—C9—C10	12.3 (2)
O1—C2—C3—Cl1	0.0 (2)	N2—C8—C9—C10	−167.92 (16)
C1—C2—C3—Cl1	179.75 (13)	C14—C9—C10—C11	0.8 (3)
C2—C3—C4—C5	0.6 (3)	C8—C9—C10—C11	−176.42 (17)
Cl1—C3—C4—C5	179.25 (14)	C9—C10—C11—C12	0.3 (3)
C3—C4—C5—C6	0.7 (3)	C10—C11—C12—O3	178.78 (17)
C3—C4—C5—Cl2	−178.61 (15)	C10—C11—C12—C13	−1.3 (3)
C4—C5—C6—C1	−1.0 (3)	O3—C12—C13—C14	−179.03 (16)
Cl2—C5—C6—C1	178.29 (14)	C11—C12—C13—C14	1.0 (3)
C2—C1—C6—C5	0.0 (3)	C12—C13—C14—C9	0.1 (3)
C7—C1—C6—C5	−178.85 (16)	C10—C9—C14—C13	−1.0 (3)
N2—N1—C7—C1	179.32 (14)	C8—C9—C14—C13	175.92 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.90	2.6164 (19)	145
O3—H3···O2i	0.82	1.85	2.658 (2)	168
N2—H2···O3ii	0.90 (1)	2.20 (2)	3.000 (2)	147 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.90	2.6164 (19)	145
O3—H3⋯O2i	0.82	1.85	2.658 (2)	168
N2—H2⋯O3ii	0.899 (10)	2.204 (16)	3.000 (2)	147 (2)

Symmetry codes: (i) ; (ii) .