N'-(2,6-Dichloro-benzyl-idene)-2-hy-droxy-benzohydrazide.

In the title compound, C(14)H(10)Cl(2)N(2)O(2), the dihedral angle between the two aromatic rings is 17.39 (4)°. An intra-molecular O-H⋯O hydrogen bond forms a six-membered R(6)(1) (1 )ring motif. In the crystal structure, inter-molecular N-H⋯O and O-H⋯O hydrogen-bonding inter-actions occur.

Related literature

For the biological activity of Schiff bases, see: El-Masry et al. (2000 ▶); Samadhiya & Halve (2001 ▶). For the synthesis of Schiff bases, see: Siddiqui et al. (2006 ▶); Iqbal et al. (2007 ▶). For applications of Schiff bases, see: Mookherjee et al. (1989 ▶); Kumar et al. (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H10Cl2N2O2

M = 309.14

Monoclinic,

a = 7.5029 (6) Å

b = 23.8363 (13) Å

c = 8.0286 (7) Å

β = 109.860 (6)°

V = 1350.45 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 180 K

0.34 × 0.26 × 0.18 mm

Data collection

Stoe IPDS-2T diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.856, T max = 0.921

21101 measured reflections

2958 independent reflections

2455 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.074

S = 1.03

2958 reflections

191 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.39 e Å−3

Data collection: X-AREA (Stoe & Cie, 1999 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035385/im2223sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035385/im2223Isup2.hkl

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

C14H10Cl2N2O2	F(000) = 632
Mr = 309.14	Dx = 1.520 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 19179 reflections
a = 7.5029 (6) Å	θ = 1.7–29.5°
b = 23.8363 (13) Å	µ = 0.48 mm−1
c = 8.0286 (7) Å	T = 180 K
β = 109.860 (6)°	Needles, white
V = 1350.45 (18) Å3	0.34 × 0.26 × 0.18 mm
Z = 4

Stoe IPDS-2T diffractometer	2958 independent reflections
Radiation source: fine-focus sealed tube	2455 reflections with I > 2σ(I)
graphite	Rint = 0.041
ω scans	θmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→9
Tmin = 0.856, Tmax = 0.921	k = −30→30
21101 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.074	w = 1/[σ2(Fo2) + (0.0408P)2 + 0.2354P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
2958 reflections	Δρmax = 0.24 e Å−3
191 parameters	Δρmin = −0.39 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0085 (19)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.66364 (6)	0.562338 (15)	0.52580 (5)	0.03982 (12)
Cl2	0.28455 (5)	0.723630 (17)	0.06158 (5)	0.03924 (12)
O1	0.77275 (17)	0.82495 (4)	0.34242 (14)	0.0369 (3)
O2	0.84369 (18)	0.92793 (5)	0.45517 (16)	0.0431 (3)
H2A	0.809 (3)	0.8981 (10)	0.383 (3)	0.065*
N1	0.72285 (16)	0.76179 (5)	0.53258 (15)	0.0239 (2)
H1	0.720 (2)	0.7541 (7)	0.636 (2)	0.029*
N2	0.63961 (16)	0.72631 (5)	0.39193 (15)	0.0233 (2)
C1	0.9163 (2)	0.90454 (6)	0.6187 (2)	0.0308 (3)
C2	1.0154 (2)	0.93943 (7)	0.7591 (2)	0.0383 (4)
H2	1.0262	0.9784	0.7396	0.046*
C3	1.0976 (2)	0.91717 (7)	0.9261 (2)	0.0409 (4)
H3	1.1648	0.9411	1.0215	0.049*
C4	1.0837 (2)	0.86024 (7)	0.9572 (2)	0.0374 (4)
H4	1.1431	0.8452	1.0723	0.045*
C5	0.9828 (2)	0.82576 (6)	0.81912 (18)	0.0281 (3)
H5	0.9726	0.7869	0.8404	0.034*
C6	0.89542 (19)	0.84719 (6)	0.64844 (18)	0.0246 (3)
C7	0.79269 (19)	0.81097 (6)	0.49710 (18)	0.0246 (3)
C8	0.56322 (19)	0.68201 (6)	0.42645 (18)	0.0242 (3)
H8	0.562 (2)	0.6739 (7)	0.542 (2)	0.029*
C9	0.47973 (19)	0.64095 (6)	0.28383 (17)	0.0252 (3)
C10	0.5196 (2)	0.58369 (6)	0.31608 (19)	0.0286 (3)
C11	0.4494 (2)	0.54288 (7)	0.1881 (2)	0.0379 (4)
H11	0.4807	0.5045	0.2145	0.045*
C12	0.3331 (3)	0.55883 (8)	0.0214 (2)	0.0439 (4)
H12	0.2849	0.5313	−0.0681	0.053*
C13	0.2862 (2)	0.61464 (8)	−0.0162 (2)	0.0406 (4)
H13	0.2048	0.6254	−0.1307	0.049*
C14	0.3588 (2)	0.65488 (6)	0.11426 (19)	0.0297 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.0478 (2)	0.02692 (19)	0.0405 (2)	0.00367 (16)	0.00954 (17)	0.00623 (15)
Cl2	0.03272 (19)	0.0378 (2)	0.0399 (2)	−0.00243 (15)	0.00277 (15)	0.01388 (16)
O1	0.0530 (7)	0.0320 (6)	0.0225 (5)	−0.0099 (5)	0.0088 (5)	0.0033 (4)
O2	0.0526 (7)	0.0255 (5)	0.0402 (7)	−0.0026 (5)	0.0013 (5)	0.0067 (5)
N1	0.0302 (6)	0.0239 (6)	0.0174 (5)	−0.0030 (4)	0.0079 (5)	−0.0014 (4)
N2	0.0253 (5)	0.0229 (5)	0.0214 (5)	0.0000 (4)	0.0077 (4)	−0.0026 (4)
C1	0.0309 (7)	0.0255 (7)	0.0350 (8)	0.0002 (5)	0.0097 (6)	0.0000 (6)
C2	0.0373 (8)	0.0269 (7)	0.0494 (9)	−0.0047 (6)	0.0130 (7)	−0.0102 (7)
C3	0.0394 (8)	0.0431 (9)	0.0382 (9)	−0.0097 (7)	0.0104 (7)	−0.0166 (7)
C4	0.0375 (8)	0.0470 (9)	0.0261 (7)	−0.0070 (7)	0.0088 (6)	−0.0059 (6)
C5	0.0273 (7)	0.0315 (7)	0.0257 (7)	−0.0033 (5)	0.0092 (6)	−0.0009 (5)
C6	0.0237 (6)	0.0254 (7)	0.0249 (7)	−0.0003 (5)	0.0084 (5)	−0.0026 (5)
C7	0.0269 (7)	0.0229 (6)	0.0232 (7)	0.0022 (5)	0.0076 (5)	0.0011 (5)
C8	0.0274 (7)	0.0229 (6)	0.0225 (7)	0.0012 (5)	0.0087 (5)	0.0011 (5)
C9	0.0272 (6)	0.0257 (7)	0.0250 (7)	−0.0032 (5)	0.0118 (5)	−0.0010 (5)
C10	0.0310 (7)	0.0272 (7)	0.0305 (7)	−0.0025 (6)	0.0142 (6)	−0.0012 (5)
C11	0.0469 (9)	0.0279 (7)	0.0450 (9)	−0.0067 (6)	0.0238 (8)	−0.0096 (7)
C12	0.0539 (10)	0.0437 (10)	0.0386 (9)	−0.0164 (8)	0.0214 (8)	−0.0176 (7)
C13	0.0431 (9)	0.0520 (10)	0.0255 (7)	−0.0143 (8)	0.0102 (7)	−0.0048 (7)
C14	0.0299 (7)	0.0324 (7)	0.0279 (7)	−0.0058 (6)	0.0114 (6)	0.0022 (6)

Cl1—C10	1.7395 (15)	C4—H4	0.9500
Cl2—C14	1.7364 (16)	C5—C6	1.399 (2)
O1—C7	1.2448 (17)	C5—H5	0.9500
O2—C1	1.3582 (19)	C6—C7	1.4763 (18)
O2—H2A	0.90 (2)	C8—C9	1.4745 (19)
N1—C7	1.3533 (18)	C8—H8	0.954 (17)
N1—N2	1.3788 (15)	C9—C14	1.396 (2)
N1—H1	0.854 (18)	C9—C10	1.402 (2)
N2—C8	1.2761 (18)	C10—C11	1.383 (2)
C1—C2	1.395 (2)	C11—C12	1.379 (3)
C1—C6	1.406 (2)	C11—H11	0.9500
C2—C3	1.378 (2)	C12—C13	1.383 (3)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.390 (3)	C13—C14	1.388 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.381 (2)
C1—O2—H2A	103.3 (15)	O1—C7—C6	121.12 (12)
C7—N1—N2	117.32 (11)	N1—C7—C6	117.68 (12)
C7—N1—H1	121.9 (11)	N2—C8—C9	118.97 (12)
N2—N1—H1	120.5 (11)	N2—C8—H8	122.3 (10)
C8—N2—N1	116.20 (11)	C9—C8—H8	118.7 (10)
O2—C1—C2	117.72 (14)	C14—C9—C10	116.02 (13)
O2—C1—C6	122.16 (13)	C14—C9—C8	124.31 (13)
C2—C1—C6	120.12 (14)	C10—C9—C8	119.67 (12)
C3—C2—C1	119.77 (15)	C11—C10—C9	122.96 (15)
C3—C2—H2	120.1	C11—C10—Cl1	117.91 (12)
C1—C2—H2	120.1	C9—C10—Cl1	119.14 (11)
C2—C3—C4	120.96 (15)	C12—C11—C10	118.86 (15)
C2—C3—H3	119.5	C12—C11—H11	120.6
C4—C3—H3	119.5	C10—C11—H11	120.6
C5—C4—C3	119.43 (15)	C11—C12—C13	120.47 (15)
C5—C4—H4	120.3	C11—C12—H12	119.8
C3—C4—H4	120.3	C13—C12—H12	119.8
C4—C5—C6	121.02 (14)	C12—C13—C14	119.64 (16)
C4—C5—H5	119.5	C12—C13—H13	120.2
C6—C5—H5	119.5	C14—C13—H13	120.2
C5—C6—C1	118.64 (13)	C13—C14—C9	122.02 (15)
C5—C6—C7	122.17 (12)	C13—C14—Cl2	117.22 (12)
C1—C6—C7	119.07 (12)	C9—C14—Cl2	120.70 (11)
O1—C7—N1	121.20 (12)
C7—N1—N2—C8	−175.33 (12)	N1—N2—C8—C9	−177.11 (11)
O2—C1—C2—C3	−177.58 (15)	N2—C8—C9—C14	−47.26 (19)
C6—C1—C2—C3	1.9 (2)	N2—C8—C9—C10	133.40 (14)
C1—C2—C3—C4	0.1 (2)	C14—C9—C10—C11	1.8 (2)
C2—C3—C4—C5	−1.3 (2)	C8—C9—C10—C11	−178.78 (13)
C3—C4—C5—C6	0.4 (2)	C14—C9—C10—Cl1	−178.18 (10)
C4—C5—C6—C1	1.6 (2)	C8—C9—C10—Cl1	1.21 (18)
C4—C5—C6—C7	177.71 (13)	C9—C10—C11—C12	−0.7 (2)
O2—C1—C6—C5	176.71 (13)	Cl1—C10—C11—C12	179.27 (12)
C2—C1—C6—C5	−2.8 (2)	C10—C11—C12—C13	−0.6 (2)
O2—C1—C6—C7	0.5 (2)	C11—C12—C13—C14	0.8 (2)
C2—C1—C6—C7	−178.98 (13)	C12—C13—C14—C9	0.4 (2)
N2—N1—C7—O1	4.02 (19)	C12—C13—C14—Cl2	−176.77 (13)
N2—N1—C7—C6	−175.26 (11)	C10—C9—C14—C13	−1.6 (2)
C5—C6—C7—O1	−155.05 (14)	C8—C9—C14—C13	179.01 (14)
C1—C6—C7—O1	21.0 (2)	C10—C9—C14—Cl2	175.41 (10)
C5—C6—C7—N1	24.23 (19)	C8—C9—C14—Cl2	−3.95 (19)
C1—C6—C7—N1	−159.71 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.85 (2)	2.38 (2)	3.165 (2)	153 (2)
N1—H1···O1i	0.85 (2)	2.45 (2)	3.158 (2)	140 (1)
O2—H2A···O1	0.90 (2)	1.78 (2)	2.608 (2)	153 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.85 (2)	2.38 (2)	3.165 (2)	153 (2)
N1—H1⋯O1i	0.85 (2)	2.45 (2)	3.158 (2)	140 (1)
O2—H2A⋯O1	0.90 (2)	1.78 (2)	2.608 (2)	153 (2)

Symmetry code: (i) .