N'-(2,4-Dichloro-benzyl-idene)-4-hy-droxy-benzohydrazide.

The title hydrazone compound, C(14)H(10)Cl(2)N(2)O(2), was synthesized by the reaction of 2,4-dichloro-benzaldehyde and 4-hy-droxy-benzohydrazide. The mol-ecule adopts an E geometry with respect to the azomethine group and the dihedral angle between the aromatic rings is 7.0 (2)°. In the crystal, mol-ecules are linked through inter-molecular N-H⋯Cl and O-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the structures and properties of hydrazones, see: Carvalho et al. (2010 ▶); Liu (2010 ▶); Fun et al. (2008 ▶); Wang et al. (2010 ▶); Singh et al. (2009 ▶); Zhu et al. (2009 ▶); Vijayakumar et al. (2009 ▶); Tameem et al. (2010 ▶).

Experimental

Crystal data

C14H10Cl2N2O2

M = 309.14

Monoclinic,

a = 7.6687 (11) Å

b = 11.9591 (17) Å

c = 15.043 (2) Å

β = 103.200 (2)°

V = 1343.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.49 mm−1

T = 298 K

0.17 × 0.13 × 0.13 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.922, T max = 0.940

6784 measured reflections

2838 independent reflections

2385 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.114

S = 1.05

2838 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.58 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536810045502/hb5726sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045502/hb5726Isup2.hkl

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

C14H10Cl2N2O2	F(000) = 632
Mr = 309.14	Dx = 1.529 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3439 reflections
a = 7.6687 (11) Å	θ = 2.2–28.1°
b = 11.9591 (17) Å	µ = 0.49 mm−1
c = 15.043 (2) Å	T = 298 K
β = 103.200 (2)°	Block, colorless
V = 1343.2 (3) Å3	0.17 × 0.13 × 0.13 mm
Z = 4

Bruker SMART CCD diffractometer	2838 independent reflections
Radiation source: fine-focus sealed tube	2385 reflections with I > 2σ(I)
graphite	Rint = 0.019
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.922, Tmax = 0.940	k = −7→15
6784 measured reflections	l = −19→17

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0636P)2 + 0.4165P] where P = (Fo2 + 2Fc2)/3
2838 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.37 e Å−3
1 restraint	Δρmin = −0.58 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	1.05089 (9)	0.19236 (5)	0.07396 (3)	0.0590 (2)
Cl2	0.99147 (8)	0.02938 (5)	−0.26115 (4)	0.05604 (19)
N1	0.7367 (2)	0.47578 (12)	−0.05039 (10)	0.0350 (3)
N2	0.7130 (2)	0.55434 (12)	0.01223 (10)	0.0363 (3)
O1	0.5166 (2)	0.65200 (12)	−0.09421 (8)	0.0476 (4)
O2	0.5103 (2)	0.96168 (11)	0.24525 (9)	0.0472 (4)
H2A	0.5329	0.9360	0.2971	0.071*
C1	0.8721 (2)	0.30387 (14)	−0.07778 (12)	0.0322 (4)
C2	0.9708 (2)	0.20915 (15)	−0.04294 (12)	0.0360 (4)
C3	1.0075 (2)	0.12484 (15)	−0.09862 (12)	0.0388 (4)
H3	1.0745	0.0628	−0.0741	0.047*
C4	0.9423 (2)	0.13500 (15)	−0.19144 (12)	0.0372 (4)
C5	0.8419 (2)	0.22625 (15)	−0.22950 (12)	0.0385 (4)
H5	0.7984	0.2313	−0.2924	0.046*
C6	0.8074 (2)	0.30948 (15)	−0.17268 (12)	0.0351 (4)
H6	0.7395	0.3709	−0.1979	0.042*
C7	0.8350 (2)	0.39312 (15)	−0.01809 (12)	0.0365 (4)
H7	0.8840	0.3892	0.0444	0.044*
C8	0.5992 (2)	0.64163 (14)	−0.01442 (11)	0.0325 (4)
C9	0.5824 (2)	0.72236 (13)	0.05731 (11)	0.0307 (4)
C10	0.6378 (2)	0.70117 (15)	0.15075 (12)	0.0358 (4)
H10	0.6907	0.6329	0.1704	0.043*
C11	0.6154 (2)	0.77948 (15)	0.21432 (11)	0.0375 (4)
H11	0.6530	0.7637	0.2763	0.045*
C12	0.5367 (2)	0.88225 (14)	0.18611 (11)	0.0338 (4)
C13	0.4802 (3)	0.90445 (15)	0.09322 (12)	0.0391 (4)
H13	0.4276	0.9729	0.0736	0.047*
C14	0.5020 (3)	0.82533 (14)	0.03025 (11)	0.0370 (4)
H14	0.4623	0.8408	−0.0317	0.044*
H2	0.767 (3)	0.542 (2)	0.0707 (8)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0820 (4)	0.0559 (3)	0.0333 (3)	0.0123 (3)	0.0010 (2)	−0.0002 (2)
Cl2	0.0620 (3)	0.0532 (3)	0.0521 (3)	0.0072 (2)	0.0113 (2)	−0.0228 (2)
N1	0.0433 (8)	0.0303 (7)	0.0336 (7)	−0.0054 (6)	0.0135 (6)	−0.0062 (6)
N2	0.0461 (8)	0.0315 (7)	0.0307 (7)	0.0008 (6)	0.0074 (6)	−0.0064 (6)
O1	0.0696 (10)	0.0455 (8)	0.0266 (6)	0.0091 (7)	0.0087 (6)	−0.0004 (5)
O2	0.0715 (9)	0.0374 (7)	0.0341 (7)	0.0030 (6)	0.0149 (7)	−0.0066 (5)
C1	0.0344 (9)	0.0301 (8)	0.0339 (8)	−0.0059 (6)	0.0117 (7)	−0.0039 (7)
C2	0.0391 (9)	0.0356 (9)	0.0327 (8)	−0.0034 (7)	0.0071 (7)	−0.0019 (7)
C3	0.0398 (10)	0.0332 (9)	0.0426 (10)	0.0007 (7)	0.0077 (8)	−0.0033 (7)
C4	0.0367 (9)	0.0364 (9)	0.0406 (9)	−0.0051 (7)	0.0132 (7)	−0.0114 (7)
C5	0.0429 (10)	0.0425 (10)	0.0308 (8)	−0.0025 (8)	0.0098 (7)	−0.0034 (7)
C6	0.0377 (9)	0.0326 (9)	0.0360 (9)	−0.0027 (7)	0.0106 (7)	0.0006 (7)
C7	0.0433 (10)	0.0348 (9)	0.0321 (8)	−0.0041 (7)	0.0097 (7)	−0.0045 (7)
C8	0.0410 (9)	0.0302 (8)	0.0279 (8)	−0.0062 (7)	0.0111 (7)	0.0000 (6)
C9	0.0356 (9)	0.0285 (8)	0.0291 (8)	−0.0048 (6)	0.0098 (6)	−0.0003 (6)
C10	0.0418 (10)	0.0357 (9)	0.0299 (8)	0.0070 (7)	0.0082 (7)	0.0037 (7)
C11	0.0443 (10)	0.0422 (10)	0.0251 (8)	0.0050 (8)	0.0060 (7)	0.0015 (7)
C12	0.0416 (9)	0.0304 (8)	0.0314 (8)	−0.0062 (7)	0.0124 (7)	−0.0032 (7)
C13	0.0576 (11)	0.0261 (8)	0.0342 (9)	0.0001 (8)	0.0117 (8)	0.0045 (7)
C14	0.0528 (11)	0.0319 (9)	0.0259 (8)	−0.0026 (7)	0.0082 (7)	0.0037 (6)

Cl1—C2	1.7369 (18)	C5—C6	1.377 (2)
Cl2—C4	1.7372 (18)	C5—H5	0.9300
N1—C7	1.270 (2)	C6—H6	0.9300
N1—N2	1.372 (2)	C7—H7	0.9300
N2—C8	1.361 (2)	C8—C9	1.475 (2)
N2—H2	0.894 (10)	C9—C10	1.396 (2)
O1—C8	1.229 (2)	C9—C14	1.396 (2)
O2—C12	1.348 (2)	C10—C11	1.377 (2)
O2—H2A	0.8200	C10—H10	0.9300
C1—C2	1.396 (2)	C11—C12	1.392 (2)
C1—C6	1.402 (2)	C11—H11	0.9300
C1—C7	1.464 (2)	C12—C13	1.391 (2)
C2—C3	1.380 (2)	C13—C14	1.376 (2)
C3—C4	1.377 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.382 (3)
C7—N1—N2	115.49 (14)	N1—C7—H7	119.5
C8—N2—N1	119.98 (14)	C1—C7—H7	119.5
C8—N2—H2	122.6 (18)	O1—C8—N2	121.20 (16)
N1—N2—H2	117.1 (18)	O1—C8—C9	122.47 (16)
C12—O2—H2A	109.5	N2—C8—C9	116.33 (14)
C2—C1—C6	117.17 (16)	C10—C9—C14	117.80 (15)
C2—C1—C7	121.73 (15)	C10—C9—C8	124.10 (15)
C6—C1—C7	121.09 (16)	C14—C9—C8	118.08 (14)
C3—C2—C1	122.21 (16)	C11—C10—C9	121.24 (16)
C3—C2—Cl1	117.13 (14)	C11—C10—H10	119.4
C1—C2—Cl1	120.66 (14)	C9—C10—H10	119.4
C4—C3—C2	118.28 (17)	C10—C11—C12	120.19 (15)
C4—C3—H3	120.9	C10—C11—H11	119.9
C2—C3—H3	120.9	C12—C11—H11	119.9
C3—C4—C5	121.92 (16)	O2—C12—C13	117.99 (16)
C3—C4—Cl2	117.99 (14)	O2—C12—C11	122.74 (15)
C5—C4—Cl2	120.08 (14)	C13—C12—C11	119.26 (16)
C6—C5—C4	118.79 (16)	C14—C13—C12	120.10 (16)
C6—C5—H5	120.6	C14—C13—H13	120.0
C4—C5—H5	120.6	C12—C13—H13	120.0
C5—C6—C1	121.61 (17)	C13—C14—C9	121.41 (15)
C5—C6—H6	119.2	C13—C14—H14	119.3
C1—C6—H6	119.2	C9—C14—H14	119.3
N1—C7—C1	120.95 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Cl2i	0.89 (1)	2.85 (1)	3.7228 (16)	167 (2)
O2—H2A···O1ii	0.82	1.97	2.7624 (19)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯Cl2i	0.89 (1)	2.85 (1)	3.7228 (16)	167 (2)
O2—H2A⋯O1ii	0.82	1.97	2.7624 (19)	162

Symmetry codes: (i) ; (ii) .