N'-(5-Chloro-2-hydroxy-benzyl-idene)-4-hydroxy-benzohydrazide.

The title Schiff base compound, C(14)H(11)ClN(2)O(3), was prepared by the reaction of 5-chloro-salicylaldehyde and 4-hydroxy-benzohydrazide. The mol-ecule exists in a trans configuration with respect to the methyl-idene group. The dihedral angle between the two benzene rings is 40.1 (2)°. An intra-molecular O-H⋯N hydrogen bond helps to stabilize the mol-ecular conformation. In the crystal structure, mol-ecules are linked into a three-dimensional network by inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For the biological properties of hydrazone compounds, see: Bedia et al. (2006 ▶); Rollas et al. (2002 ▶); Fun et al. (2008 ▶). For the structures of hydrazone compounds we have reported previously, see: Qiu, Fang et al. (2006 ▶); Qiu, Luo et al., (2006a ▶,b ▶); Qiu, Xu et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures see: Singh et al. (2007 ▶); Narayana et al. (2007 ▶); Cui et al. (2007 ▶); Diao et al. (2008 ▶).

Experimental

Crystal data

C14H11ClN2O3

M = 290.70

Orthorhombic,

a = 9.423 (1) Å

b = 9.839 (1) Å

c = 13.770 (1) Å

V = 1276.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 298 K

0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.950, T max = 0.955

7398 measured reflections

2231 independent reflections

2144 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.071

S = 1.06

2231 reflections

187 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.32 e Å−3

Absolute structure: Flack (1983 ▶), 784 Friedel pairs

Flack parameter: −0.01 (6)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901215X/sj2605sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901215X/sj2605Isup2.hkl

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

C14H11ClN2O3	F(000) = 600
Mr = 290.70	Dx = 1.513 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4763 reflections
a = 9.423 (1) Å	θ = 2.5–30.6°
b = 9.839 (1) Å	µ = 0.31 mm−1
c = 13.770 (1) Å	T = 298 K
V = 1276.7 (2) Å3	Block, colourless
Z = 4	0.17 × 0.15 × 0.15 mm

Bruker SMART CCD diffractometer	2231 independent reflections
Radiation source: fine-focus sealed tube	2144 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
Tmin = 0.950, Tmax = 0.955	k = −12→12
7398 measured reflections	l = −17→11

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.026	w = 1/[σ2(Fo2) + (0.0409P)2 + 0.1827P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.071	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.21 e Å−3
2231 reflections	Δρmin = −0.32 e Å−3
187 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraints	Extinction coefficient: 0.034 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 784 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.01 (6)

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	0.74914 (6)	0.47741 (5)	1.21657 (5)	0.05224 (15)
N1	0.99352 (15)	0.30628 (14)	0.80967 (10)	0.0316 (3)
N2	0.94949 (14)	0.28112 (13)	0.71621 (12)	0.0319 (3)
O1	1.19292 (14)	0.32175 (17)	0.94031 (11)	0.0504 (4)
H1	1.1598	0.3057	0.8865	0.076*
O2	1.14143 (12)	0.14658 (12)	0.69247 (10)	0.0370 (3)
O3	0.84616 (17)	0.10538 (15)	0.27816 (10)	0.0505 (4)
H3	0.8733	0.0312	0.2583	0.076*
C1	0.94953 (17)	0.38640 (15)	0.96863 (13)	0.0312 (3)
C2	1.08639 (18)	0.35624 (17)	1.00215 (14)	0.0346 (4)
C3	1.1165 (2)	0.36019 (19)	1.10078 (15)	0.0403 (4)
H3A	1.2072	0.3386	1.1225	0.048*
C4	1.0133 (2)	0.39569 (17)	1.16663 (14)	0.0391 (4)
H4	1.0332	0.3960	1.2328	0.047*
C5	0.87956 (19)	0.43088 (17)	1.13363 (14)	0.0362 (4)
C6	0.84744 (18)	0.42738 (18)	1.03619 (14)	0.0352 (4)
H6	0.7573	0.4524	1.0152	0.042*
C7	0.90835 (18)	0.36642 (16)	0.86788 (13)	0.0325 (3)
H7	0.8207	0.3972	0.8459	0.039*
C8	1.03211 (17)	0.20101 (16)	0.65983 (13)	0.0292 (3)
C9	0.98366 (16)	0.17900 (16)	0.55911 (12)	0.0296 (3)
C10	1.03520 (17)	0.06631 (17)	0.50845 (14)	0.0335 (4)
H10	1.0998	0.0084	0.5384	0.040*
C11	0.99177 (18)	0.03955 (17)	0.41486 (14)	0.0350 (4)
H11	1.0265	−0.0361	0.3821	0.042*
C12	0.89604 (19)	0.12597 (18)	0.36973 (13)	0.0352 (4)
C13	0.8457 (2)	0.2394 (2)	0.41833 (15)	0.0450 (5)
H13	0.7826	0.2980	0.3876	0.054*
C14	0.8889 (2)	0.26545 (18)	0.51195 (14)	0.0392 (4)
H14	0.8544	0.3417	0.5441	0.047*
H2	0.8598 (14)	0.303 (3)	0.703 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0578 (3)	0.0676 (3)	0.0313 (2)	0.0148 (2)	0.0054 (2)	−0.0062 (3)
N1	0.0343 (7)	0.0371 (7)	0.0235 (8)	−0.0016 (5)	−0.0046 (6)	−0.0003 (6)
N2	0.0319 (7)	0.0408 (7)	0.0229 (7)	0.0001 (5)	−0.0045 (7)	−0.0009 (6)
O1	0.0365 (7)	0.0791 (10)	0.0354 (8)	0.0131 (7)	−0.0033 (6)	−0.0060 (7)
O2	0.0323 (6)	0.0466 (6)	0.0322 (7)	0.0039 (5)	−0.0061 (5)	0.0025 (5)
O3	0.0679 (10)	0.0545 (8)	0.0289 (8)	0.0089 (6)	−0.0118 (7)	−0.0097 (6)
C1	0.0344 (8)	0.0322 (8)	0.0271 (9)	−0.0001 (6)	−0.0049 (7)	−0.0006 (6)
C2	0.0352 (8)	0.0376 (8)	0.0311 (9)	0.0014 (6)	−0.0033 (8)	−0.0024 (7)
C3	0.0400 (10)	0.0450 (9)	0.0358 (11)	0.0036 (7)	−0.0127 (8)	−0.0025 (8)
C4	0.0531 (11)	0.0398 (8)	0.0244 (9)	0.0025 (7)	−0.0103 (8)	−0.0032 (7)
C5	0.0444 (9)	0.0359 (8)	0.0283 (9)	0.0031 (7)	0.0005 (7)	−0.0044 (7)
C6	0.0350 (8)	0.0406 (8)	0.0300 (9)	0.0035 (7)	−0.0046 (7)	−0.0008 (7)
C7	0.0317 (8)	0.0386 (8)	0.0271 (9)	0.0007 (6)	−0.0056 (7)	0.0011 (7)
C8	0.0298 (8)	0.0318 (7)	0.0261 (9)	−0.0043 (6)	−0.0007 (6)	0.0027 (6)
C9	0.0304 (7)	0.0342 (7)	0.0243 (9)	−0.0013 (6)	0.0003 (6)	0.0019 (6)
C10	0.0309 (8)	0.0371 (8)	0.0327 (10)	0.0039 (6)	−0.0011 (7)	−0.0011 (7)
C11	0.0358 (9)	0.0370 (8)	0.0321 (10)	0.0015 (6)	0.0030 (7)	−0.0058 (7)
C12	0.0392 (9)	0.0426 (9)	0.0239 (9)	−0.0033 (7)	−0.0011 (7)	−0.0004 (7)
C13	0.0593 (12)	0.0446 (9)	0.0311 (10)	0.0158 (8)	−0.0110 (9)	0.0004 (8)
C14	0.0527 (10)	0.0360 (8)	0.0290 (9)	0.0111 (7)	−0.0052 (8)	−0.0040 (7)

Cl1—C5	1.7391 (19)	C4—C5	1.384 (3)
N1—C7	1.279 (2)	C4—H4	0.9300
N1—N2	1.375 (2)	C5—C6	1.376 (3)
N2—C8	1.353 (2)	C6—H6	0.9300
N2—H2	0.892 (10)	C7—H7	0.9300
O1—C2	1.359 (2)	C8—C9	1.476 (2)
O1—H1	0.8200	C9—C14	1.394 (2)
O2—C8	1.245 (2)	C9—C10	1.397 (2)
O3—C12	1.361 (2)	C10—C11	1.378 (3)
O3—H3	0.8200	C10—H10	0.9300
C1—C6	1.398 (2)	C11—C12	1.387 (2)
C1—C2	1.402 (2)	C11—H11	0.9300
C1—C7	1.454 (2)	C12—C13	1.385 (3)
C2—C3	1.388 (3)	C13—C14	1.376 (3)
C3—C4	1.374 (3)	C13—H13	0.9300
C3—H3A	0.9300	C14—H14	0.9300
C7—N1—N2	118.72 (14)	N1—C7—C1	119.54 (15)
C8—N2—N1	117.94 (13)	N1—C7—H7	120.2
C8—N2—H2	125 (2)	C1—C7—H7	120.2
N1—N2—H2	116 (2)	O2—C8—N2	121.31 (16)
C2—O1—H1	109.5	O2—C8—C9	122.14 (15)
C12—O3—H3	109.5	N2—C8—C9	116.53 (14)
C6—C1—C2	118.37 (16)	C14—C9—C10	118.32 (16)
C6—C1—C7	119.37 (15)	C14—C9—C8	123.12 (15)
C2—C1—C7	122.09 (16)	C10—C9—C8	118.56 (14)
O1—C2—C3	117.99 (16)	C11—C10—C9	121.03 (16)
O1—C2—C1	121.73 (17)	C11—C10—H10	119.5
C3—C2—C1	120.28 (16)	C9—C10—H10	119.5
C4—C3—C2	120.55 (16)	C10—C11—C12	119.69 (16)
C4—C3—H3A	119.7	C10—C11—H11	120.2
C2—C3—H3A	119.7	C12—C11—H11	120.2
C3—C4—C5	119.41 (17)	O3—C12—C13	116.71 (16)
C3—C4—H4	120.3	O3—C12—C11	123.28 (16)
C5—C4—H4	120.3	C13—C12—C11	120.01 (17)
C6—C5—C4	120.95 (18)	C14—C13—C12	120.13 (17)
C6—C5—Cl1	119.44 (14)	C14—C13—H13	119.9
C4—C5—Cl1	119.59 (15)	C12—C13—H13	119.9
C5—C6—C1	120.32 (16)	C13—C14—C9	120.80 (16)
C5—C6—H6	119.8	C13—C14—H14	119.6
C1—C6—H6	119.8	C9—C14—H14	119.6

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.89 (1)	2.12 (1)	3.0065 (18)	172 (3)
O3—H3···O2ii	0.82	1.98	2.7479 (19)	157
O1—H1···N1	0.82	1.89	2.6057 (19)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.892 (10)	2.121 (11)	3.0065 (18)	172 (3)
O3—H3⋯O2ii	0.82	1.98	2.7479 (19)	157
O1—H1⋯N1	0.82	1.89	2.6057 (19)	145

Symmetry codes: (i) ; (ii) .