N'-(2,4-Dichloro-benzyl-idene)-2-hydr-oxy-3-methyl-benzohydrazide.

In the title compound, C(15)H(12)Cl(2)N(2)O(2), the dihedral angle between the two benzene rings is 6.3 (2)°. The mol-ecule adopts an E configuration with respect to the C=N bond. An intra-molecular O-H⋯O hydrogen bond is observed. In the crystal structure, the mol-ecules are linked through inter-molecular N-H⋯O and C-H⋯O hydrogen bonds to form chains running along [101].

Related literature

For the biological properties of hydrazone compounds, see: Patil et al. (2010 ▶); Cukurovali et al. (2006 ▶). For related structures, see: Mohd Lair et al. (2009 ▶); Lin & Sang (2009 ▶); Suleiman Gwaram et al. (2010 ▶); Li & Ban (2009 ▶); Lo & Ng (2009 ▶); Ning & Xu (2009 ▶); Zhu et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H12Cl2N2O2

M = 323.17

Monoclinic,

a = 7.137 (1) Å

b = 28.146 (2) Å

c = 8.130 (1) Å

β = 115.098 (1)°

V = 1478.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.44 mm−1

T = 298 K

0.20 × 0.20 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.917, T max = 0.928

8543 measured reflections

3211 independent reflections

2439 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.130

S = 1.08

3211 reflections

195 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810012419/ci5073sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012419/ci5073Isup2.hkl

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

C15H12Cl2N2O2	F(000) = 664
Mr = 323.17	Dx = 1.451 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3312 reflections
a = 7.137 (1) Å	θ = 2.7–26.7°
b = 28.146 (2) Å	µ = 0.44 mm−1
c = 8.130 (1) Å	T = 298 K
β = 115.098 (1)°	Block, colourless
V = 1478.9 (3) Å3	0.20 × 0.20 × 0.17 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3211 independent reflections
Radiation source: fine-focus sealed tube	2439 reflections with I > 2σ(I)
graphite	Rint = 0.080
ω scans	θmax = 27.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→9
Tmin = 0.917, Tmax = 0.928	k = −35→29
8543 measured reflections	l = −10→10

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0634P)2 + 0.0199P] where P = (Fo2 + 2Fc2)/3
3211 reflections	(Δ/σ)max = 0.001
195 parameters	Δρmax = 0.20 e Å−3
1 restraint	Δρmin = −0.34 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.08171 (10)	0.072034 (18)	0.35298 (7)	0.0675 (2)
Cl2	0.28271 (12)	0.02969 (2)	1.04608 (9)	0.0896 (3)
N1	0.2165 (2)	0.21754 (5)	0.51447 (19)	0.0456 (3)
N2	0.1732 (2)	0.24652 (5)	0.36590 (19)	0.0461 (4)
O1	0.2584 (2)	0.39071 (4)	0.38436 (19)	0.0607 (4)
H1	0.3024	0.3723	0.4706	0.091*
O2	0.3710 (2)	0.30580 (5)	0.54178 (17)	0.0612 (4)
C1	0.1840 (3)	0.13994 (6)	0.6149 (2)	0.0418 (4)
C2	0.1588 (3)	0.09173 (6)	0.5740 (2)	0.0456 (4)
C3	0.1937 (3)	0.05770 (7)	0.7075 (3)	0.0532 (5)
H3	0.1815	0.0255	0.6790	0.064*
C4	0.2466 (3)	0.07250 (7)	0.8822 (3)	0.0564 (5)
C5	0.2684 (3)	0.11985 (7)	0.9281 (3)	0.0571 (5)
H5	0.3025	0.1293	1.0470	0.068*
C6	0.2390 (3)	0.15312 (7)	0.7953 (2)	0.0507 (4)
H6	0.2562	0.1851	0.8263	0.061*
C7	0.1512 (3)	0.17531 (6)	0.4737 (2)	0.0447 (4)
H7	0.0814	0.1667	0.3522	0.054*
C8	0.2616 (3)	0.28989 (6)	0.3889 (2)	0.0440 (4)
C9	0.2212 (2)	0.31687 (6)	0.2219 (2)	0.0412 (4)
C10	0.2190 (3)	0.36649 (6)	0.2284 (2)	0.0458 (4)
C11	0.1737 (3)	0.39357 (7)	0.0725 (3)	0.0530 (5)
C12	0.1414 (3)	0.36996 (7)	−0.0855 (3)	0.0598 (5)
H12	0.1124	0.3876	−0.1902	0.072*
C13	0.1503 (3)	0.32088 (8)	−0.0946 (3)	0.0595 (5)
H13	0.1306	0.3060	−0.2028	0.071*
C14	0.1888 (3)	0.29443 (6)	0.0593 (2)	0.0487 (4)
H14	0.1932	0.2615	0.0544	0.058*
C15	0.1625 (4)	0.44689 (7)	0.0806 (4)	0.0719 (6)
H15A	0.1534	0.4603	−0.0312	0.108*
H15B	0.2845	0.4586	0.1797	0.108*
H15C	0.0425	0.4558	0.0983	0.108*
H2	0.077 (3)	0.2377 (8)	0.2565 (18)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.1002 (5)	0.0532 (3)	0.0537 (3)	−0.0007 (3)	0.0369 (3)	−0.0057 (2)
Cl2	0.1246 (6)	0.0848 (5)	0.0756 (4)	0.0201 (4)	0.0580 (4)	0.0368 (3)
N1	0.0454 (8)	0.0445 (8)	0.0405 (7)	−0.0003 (6)	0.0122 (6)	0.0052 (6)
N2	0.0480 (9)	0.0424 (8)	0.0379 (7)	−0.0048 (6)	0.0083 (6)	0.0040 (6)
O1	0.0731 (10)	0.0438 (7)	0.0648 (9)	−0.0015 (6)	0.0290 (8)	−0.0077 (6)
O2	0.0725 (9)	0.0499 (8)	0.0422 (7)	−0.0099 (6)	0.0060 (7)	−0.0029 (6)
C1	0.0380 (9)	0.0467 (9)	0.0401 (9)	0.0001 (7)	0.0158 (7)	0.0036 (7)
C2	0.0472 (10)	0.0483 (10)	0.0472 (9)	0.0026 (7)	0.0256 (8)	0.0032 (7)
C3	0.0599 (12)	0.0453 (10)	0.0631 (12)	0.0056 (8)	0.0344 (10)	0.0104 (9)
C4	0.0585 (12)	0.0638 (13)	0.0545 (11)	0.0116 (9)	0.0312 (10)	0.0189 (9)
C5	0.0597 (12)	0.0695 (13)	0.0416 (9)	0.0060 (9)	0.0211 (9)	0.0056 (9)
C6	0.0516 (11)	0.0515 (11)	0.0451 (10)	−0.0009 (8)	0.0168 (9)	0.0011 (8)
C7	0.0437 (10)	0.0457 (10)	0.0409 (9)	−0.0019 (7)	0.0143 (8)	0.0015 (7)
C8	0.0411 (9)	0.0408 (9)	0.0436 (9)	0.0018 (7)	0.0118 (8)	0.0015 (7)
C9	0.0346 (8)	0.0412 (9)	0.0425 (9)	−0.0015 (6)	0.0111 (7)	0.0013 (7)
C10	0.0369 (9)	0.0419 (9)	0.0550 (11)	0.0006 (7)	0.0159 (8)	0.0032 (8)
C11	0.0398 (10)	0.0487 (10)	0.0666 (12)	0.0021 (7)	0.0188 (9)	0.0103 (9)
C12	0.0507 (12)	0.0641 (13)	0.0593 (12)	−0.0033 (9)	0.0181 (10)	0.0198 (10)
C13	0.0579 (12)	0.0746 (14)	0.0435 (10)	−0.0112 (10)	0.0191 (9)	−0.0023 (9)
C14	0.0467 (10)	0.0469 (10)	0.0489 (10)	−0.0041 (8)	0.0167 (8)	−0.0011 (8)
C15	0.0662 (14)	0.0479 (12)	0.0980 (17)	0.0069 (9)	0.0313 (13)	0.0206 (11)

Cl1—C2	1.7319 (18)	C5—H5	0.93
Cl2—C4	1.7323 (18)	C6—H6	0.93
N1—C7	1.268 (2)	C7—H7	0.93
N1—N2	1.3795 (19)	C8—C9	1.474 (2)
N2—C8	1.350 (2)	C9—C14	1.393 (2)
N2—H2	0.898 (10)	C9—C10	1.398 (2)
O1—C10	1.360 (2)	C10—C11	1.394 (3)
O1—H1	0.82	C11—C12	1.376 (3)
O2—C8	1.2376 (19)	C11—C15	1.506 (3)
C1—C2	1.391 (3)	C12—C13	1.386 (3)
C1—C6	1.398 (2)	C12—H12	0.93
C1—C7	1.461 (2)	C13—C14	1.379 (3)
C2—C3	1.389 (2)	C13—H13	0.93
C3—C4	1.371 (3)	C14—H14	0.93
C3—H3	0.93	C15—H15A	0.96
C4—C5	1.375 (3)	C15—H15B	0.96
C5—C6	1.376 (3)	C15—H15C	0.96
C7—N1—N2	113.86 (14)	O2—C8—C9	122.17 (16)
C8—N2—N1	119.69 (14)	N2—C8—C9	116.17 (14)
C8—N2—H2	120.2 (15)	C14—C9—C10	119.26 (16)
N1—N2—H2	119.8 (15)	C14—C9—C8	121.98 (16)
C10—O1—H1	109.5	C10—C9—C8	118.75 (15)
C2—C1—C6	117.41 (16)	O1—C10—C11	116.74 (17)
C2—C1—C7	121.03 (15)	O1—C10—C9	122.35 (16)
C6—C1—C7	121.56 (16)	C11—C10—C9	120.91 (17)
C3—C2—C1	121.58 (17)	C12—C11—C10	117.83 (17)
C3—C2—Cl1	117.58 (14)	C12—C11—C15	122.08 (19)
C1—C2—Cl1	120.84 (13)	C10—C11—C15	120.09 (19)
C4—C3—C2	118.68 (18)	C11—C12—C13	122.54 (18)
C4—C3—H3	120.7	C11—C12—H12	118.7
C2—C3—H3	120.7	C13—C12—H12	118.7
C3—C4—C5	121.67 (17)	C14—C13—C12	119.04 (19)
C3—C4—Cl2	118.12 (16)	C14—C13—H13	120.5
C5—C4—Cl2	120.20 (15)	C12—C13—H13	120.5
C4—C5—C6	119.02 (18)	C13—C14—C9	120.33 (18)
C4—C5—H5	120.5	C13—C14—H14	119.8
C6—C5—H5	120.5	C9—C14—H14	119.8
C5—C6—C1	121.58 (17)	C11—C15—H15A	109.5
C5—C6—H6	119.2	C11—C15—H15B	109.5
C1—C6—H6	119.2	H15A—C15—H15B	109.5
N1—C7—C1	120.98 (16)	C11—C15—H15C	109.5
N1—C7—H7	119.5	H15A—C15—H15C	109.5
C1—C7—H7	119.5	H15B—C15—H15C	109.5
O2—C8—N2	121.66 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.96	2.6689 (19)	144
N2—H2···O2i	0.90 (1)	2.13 (1)	2.9905 (19)	161 (2)
C7—H7···O2i	0.93	2.45	3.264 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.96	2.6689 (19)	144
N2—H2⋯O2i	0.90 (1)	2.13 (1)	2.9905 (19)	161 (2)
C7—H7⋯O2i	0.93	2.45	3.264 (2)	146

Symmetry code: (i) .