(E)-6-Chloro-N'-(3,5-dichloro-2-hydroxy-benzyl-idene)-nicotinohydrazide.

The title Schiff base compound, C(13)H(8)Cl(3)N(3)O(2), was synthesized by the condensation reaction of 3,5-dichloro-salicyl-aldehyde with 6-chloro-nicotinic acid hydrazide in 95% ethanol. The mol-ecule is nearly planar, with a dihedral angle of 1.9 (2)° between the aromatic ring planes, and an intra-molecular O-H⋯N hydrogen bond is observed. In the crystal, the mol-ecules are connected by inter-molecular N-H⋯O hydrogen bonds into infinite chains propagating in [100].

Related literature

For general background, see: Kim et al. (2005 ▶); Fan et al. (2007 ▶). For background on the biological activities of Schiff bases, see: Ren et al. (2002 ▶); Takeuchi et al. (1998 ▶). For a related structure, see: Zhi (2008 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H8Cl3N3O2

M = 344.57

Monoclinic,

a = 4.8920 (10) Å

b = 18.014 (4) Å

c = 16.112 (3) Å

β = 97.90 (3)°

V = 1406.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.66 mm−1

T = 298 K

0.27 × 0.23 × 0.23 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Siemens, 1996 ▶) T min = 0.842, T max = 0.864

7275 measured reflections

2478 independent reflections

1323 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.114

S = 1.01

2478 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.40 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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 global, I. DOI: 10.1107/S1600536809007272/hb2920sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007272/hb2920Isup2.hkl

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

C13H8Cl3N3O2	F(000) = 696
Mr = 344.57	Dx = 1.627 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 669 reflections
a = 4.892 (1) Å	θ = 2.6–18.8°
b = 18.014 (4) Å	µ = 0.66 mm−1
c = 16.112 (3) Å	T = 298 K
β = 97.90 (3)°	Block, light yellow
V = 1406.4 (5) Å3	0.27 × 0.23 × 0.23 mm
Z = 4

Siemens SMART CCD diffractometer	2478 independent reflections
Radiation source: fine-focus sealed tube	1323 reflections with I > 2σ(I)
graphite	Rint = 0.078
φ and ω scans	θmax = 25.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −5→5
Tmin = 0.842, Tmax = 0.864	k = −15→21
7275 measured reflections	l = −19→15

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0343P)2 + 0.2069P] where P = (Fo2 + 2Fc2)/3
2478 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.40 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	0.3842 (2)	0.62724 (6)	0.45177 (7)	0.0534 (3)
Cl2	1.2166 (3)	0.50424 (7)	0.65897 (7)	0.0651 (4)
Cl3	1.2331 (3)	1.28010 (7)	0.69130 (8)	0.0698 (4)
N1	0.9665 (7)	0.8466 (2)	0.6071 (2)	0.0471 (9)
N2	1.0608 (7)	0.91708 (18)	0.6266 (2)	0.0474 (9)
H2	1.2318	0.9261	0.6437	0.057*
O1	0.6119 (6)	0.76626 (15)	0.51866 (18)	0.0542 (8)
H1	0.6800	0.8046	0.5397	0.081*
O2	0.6214 (6)	0.95721 (16)	0.59872 (19)	0.0619 (9)
C1	1.0059 (8)	0.7165 (2)	0.6081 (2)	0.0408 (10)
C2	0.7633 (8)	0.7076 (2)	0.5502 (2)	0.0399 (10)
C3	0.6750 (8)	0.6374 (2)	0.5262 (2)	0.0411 (11)
C4	0.8115 (8)	0.5751 (2)	0.5595 (3)	0.0455 (11)
H4	0.7479	0.5280	0.5428	0.055*
C5	1.0456 (9)	0.5834 (2)	0.6182 (3)	0.0461 (11)
C6	1.1444 (9)	0.6532 (2)	0.6417 (3)	0.0450 (11)
H6	1.3036	0.6581	0.6801	0.054*
C7	1.1106 (9)	0.7906 (3)	0.6314 (2)	0.0452 (11)
H7	1.2817	0.7964	0.6639	0.054*
C8	0.8673 (9)	0.9716 (2)	0.6171 (3)	0.0450 (11)
C9	0.9672 (8)	1.0483 (2)	0.6324 (3)	0.0410 (10)
C10	0.8110 (9)	1.1062 (2)	0.5936 (3)	0.0506 (12)
H10	0.6519	1.0962	0.5566	0.061*
C11	0.8935 (9)	1.1786 (3)	0.6102 (3)	0.0543 (12)
H11	0.7949	1.2183	0.5842	0.065*
C12	1.1270 (9)	1.1895 (2)	0.6666 (3)	0.0477 (12)
N3	1.2807 (7)	1.1365 (2)	0.7059 (2)	0.0502 (10)
C13	1.1988 (9)	1.0670 (2)	0.6874 (3)	0.0493 (11)
H13	1.3051	1.0285	0.7133	0.059*

	U11	U22	U33	U12	U13	U23
Cl1	0.0452 (7)	0.0496 (7)	0.0632 (8)	−0.0075 (6)	0.0002 (5)	−0.0027 (6)
Cl2	0.0715 (9)	0.0529 (8)	0.0676 (8)	0.0141 (7)	−0.0015 (6)	0.0027 (6)
Cl3	0.0842 (10)	0.0520 (8)	0.0722 (9)	−0.0184 (7)	0.0071 (7)	−0.0060 (7)
N1	0.040 (2)	0.040 (2)	0.062 (3)	−0.0058 (19)	0.0091 (18)	−0.0038 (19)
N2	0.036 (2)	0.037 (2)	0.067 (3)	−0.0058 (19)	−0.0010 (18)	−0.0074 (19)
O1	0.0454 (19)	0.045 (2)	0.069 (2)	−0.0041 (16)	−0.0032 (15)	−0.0010 (16)
O2	0.0317 (19)	0.060 (2)	0.092 (2)	−0.0082 (16)	0.0027 (16)	−0.0115 (18)
C1	0.030 (2)	0.045 (3)	0.048 (3)	−0.004 (2)	0.010 (2)	−0.005 (2)
C2	0.034 (3)	0.035 (3)	0.050 (3)	−0.002 (2)	0.005 (2)	−0.001 (2)
C3	0.030 (2)	0.049 (3)	0.043 (3)	−0.002 (2)	0.0032 (19)	0.000 (2)
C4	0.048 (3)	0.038 (3)	0.053 (3)	−0.005 (2)	0.016 (2)	−0.003 (2)
C5	0.048 (3)	0.047 (3)	0.044 (3)	0.006 (2)	0.010 (2)	0.002 (2)
C6	0.041 (3)	0.049 (3)	0.045 (3)	0.005 (2)	0.007 (2)	−0.004 (2)
C7	0.035 (3)	0.053 (3)	0.048 (3)	−0.007 (2)	0.006 (2)	−0.008 (2)
C8	0.040 (3)	0.046 (3)	0.049 (3)	−0.008 (2)	0.006 (2)	−0.005 (2)
C9	0.033 (3)	0.041 (3)	0.049 (3)	−0.005 (2)	0.006 (2)	−0.005 (2)
C10	0.041 (3)	0.053 (3)	0.055 (3)	−0.008 (2)	−0.001 (2)	−0.001 (2)
C11	0.053 (3)	0.048 (3)	0.061 (3)	−0.003 (2)	0.003 (2)	0.006 (2)
C12	0.052 (3)	0.046 (3)	0.047 (3)	−0.015 (2)	0.013 (2)	−0.001 (2)
N3	0.043 (2)	0.048 (3)	0.057 (2)	−0.004 (2)	−0.0001 (18)	−0.006 (2)
C13	0.043 (3)	0.044 (3)	0.061 (3)	−0.002 (2)	0.004 (2)	−0.006 (2)

Cl1—C3	1.739 (4)	C4—C5	1.389 (5)
Cl2—C5	1.736 (4)	C4—H4	0.9300
Cl3—C12	1.742 (4)	C5—C6	1.382 (5)
N1—C7	1.263 (5)	C6—H6	0.9300
N1—N2	1.372 (4)	C7—H7	0.9300
N2—C8	1.358 (5)	C8—C9	1.474 (5)
N2—H2	0.8600	C9—C13	1.380 (5)
O1—C2	1.349 (4)	C9—C10	1.391 (5)
O1—H1	0.8200	C10—C11	1.380 (6)
O2—C8	1.227 (5)	C10—H10	0.9300
C1—C6	1.396 (5)	C11—C12	1.373 (6)
C1—C2	1.414 (5)	C11—H11	0.9300
C1—C7	1.460 (5)	C12—N3	1.321 (5)
C2—C3	1.375 (5)	N3—C13	1.337 (5)
C3—C4	1.376 (5)	C13—H13	0.9300
C7—N1—N2	120.9 (4)	N1—C7—C1	119.3 (4)
C8—N2—N1	115.9 (4)	N1—C7—H7	120.3
C8—N2—H2	122.1	C1—C7—H7	120.3
N1—N2—H2	122.1	O2—C8—N2	121.3 (4)
C2—O1—H1	109.5	O2—C8—C9	122.0 (4)
C6—C1—C2	118.8 (4)	N2—C8—C9	116.7 (4)
C6—C1—C7	120.8 (4)	C13—C9—C10	117.2 (4)
C2—C1—C7	120.4 (4)	C13—C9—C8	124.0 (4)
O1—C2—C3	118.6 (4)	C10—C9—C8	118.6 (4)
O1—C2—C1	121.8 (4)	C11—C10—C9	119.6 (4)
C3—C2—C1	119.5 (4)	C11—C10—H10	120.2
C2—C3—C4	121.5 (4)	C9—C10—H10	120.2
C2—C3—Cl1	119.1 (3)	C12—C11—C10	117.3 (4)
C4—C3—Cl1	119.4 (3)	C12—C11—H11	121.4
C3—C4—C5	119.3 (4)	C10—C11—H11	121.4
C3—C4—H4	120.4	N3—C12—C11	125.5 (4)
C5—C4—H4	120.4	N3—C12—Cl3	115.8 (3)
C6—C5—C4	120.6 (4)	C11—C12—Cl3	118.7 (4)
C6—C5—Cl2	120.8 (4)	C12—N3—C13	115.9 (4)
C4—C5—Cl2	118.6 (3)	N3—C13—C9	124.5 (4)
C5—C6—C1	120.3 (4)	N3—C13—H13	117.7
C5—C6—H6	119.9	C9—C13—H13	117.7
C1—C6—H6	119.9

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.86	2.20	2.930 (4)	142
O1—H1···N1	0.82	1.82	2.540 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.86	2.20	2.930 (4)	142
O1—H1⋯N1	0.82	1.82	2.540 (4)	147

Symmetry code: (i) .