(E)-N'-(3,5-Dichloro-2-hy-droxy-benzyl-idene)-2-meth-oxy-benzohydrazide.

In the title compound, C(15)H(12)Cl(2)N(2)O(3), the dihedral angle between the two substituted aromatic rings is 5.4 (4)°. Intra-molecular O-H⋯N and N-H⋯O hydrogen bonds affect the planarity of the molcular conformation, with a mean deviation from the plane defined by the non-H atoms of 0.062 (2) Å. The mol-ecule exists in a trans configuration with respect to the methyl-idene unit. In the crystal, mol-ecules are linked by N-H⋯O inter-actions.

Related literature

For the crystal structures of hydrazone compounds, see: Li (2011 ▶); Hashemian et al. (2011 ▶); Lei (2011 ▶); Shalash et al. (2010 ▶).

Experimental

Crystal data

C15H12Cl2N2O3

M = 339.17

Monoclinic,

a = 10.845 (7) Å

b = 12.771 (8) Å

c = 10.856 (7) Å

β = 96.683 (7)°

V = 1493.4 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 298 K

0.18 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.924, T max = 0.928

4586 measured reflections

2978 independent reflections

2011 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.133

S = 1.02

2978 reflections

204 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶), 1272 Friedel pairs

Flack parameter: 0.10 (10)

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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681102366X/om2438sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102366X/om2438Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681102366X/om2438Isup3.cml

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

C15H12Cl2N2O3	F(000) = 696
Mr = 339.17	Dx = 1.508 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 816 reflections
a = 10.845 (7) Å	θ = 2.4–24.3°
b = 12.771 (8) Å	µ = 0.45 mm−1
c = 10.856 (7) Å	T = 298 K
β = 96.683 (7)°	Block, colorless
V = 1493.4 (16) Å3	0.18 × 0.18 × 0.17 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2978 independent reflections
Radiation source: fine-focus sealed tube	2011 reflections with I > 2σ(I)
graphite	Rint = 0.050
ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
Tmin = 0.924, Tmax = 0.928	k = −16→12
4586 measured reflections	l = −13→14

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)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.133	w = 1/[σ2(Fo2) + (0.0425P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2978 reflections	Δρmax = 0.28 e Å−3
204 parameters	Δρmin = −0.28 e Å−3
4 restraints	Absolute structure: Flack (1983), 1272 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.10 (10)

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 > 2sigma(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	0.40120 (15)	0.77322 (10)	0.22803 (13)	0.0652 (4)
Cl2	0.47525 (14)	0.96477 (10)	0.67126 (14)	0.0658 (4)
N1	0.6075 (4)	0.4977 (3)	0.5532 (3)	0.0389 (9)
N2	0.6498 (4)	0.4042 (3)	0.6052 (3)	0.0436 (10)
O1	0.5144 (3)	0.5940 (2)	0.3592 (3)	0.0461 (8)
H1	0.5450	0.5443	0.3998	0.069*
O2	0.6238 (4)	0.3303 (2)	0.4167 (3)	0.0581 (10)
O3	0.7634 (3)	0.2894 (3)	0.7842 (3)	0.0535 (10)
C1	0.5091 (4)	0.6771 (3)	0.4333 (4)	0.0353 (10)
C2	0.4584 (4)	0.7706 (4)	0.3839 (4)	0.0436 (12)
C3	0.4487 (4)	0.8590 (4)	0.4551 (5)	0.0464 (12)
H3	0.4142	0.9202	0.4198	0.056*
C4	0.4913 (5)	0.8547 (4)	0.5798 (4)	0.0450 (12)
C5	0.5424 (4)	0.7637 (4)	0.6342 (4)	0.0418 (12)
H5	0.5708	0.7621	0.7184	0.050*
C6	0.5504 (4)	0.6748 (3)	0.5611 (4)	0.0360 (10)
C7	0.6003 (4)	0.5782 (4)	0.6203 (4)	0.0421 (11)
H7	0.6261	0.5760	0.7050	0.051*
C8	0.6559 (4)	0.3220 (3)	0.5280 (4)	0.0376 (11)
C9	0.7044 (4)	0.2206 (3)	0.5831 (4)	0.0374 (11)
C10	0.6993 (5)	0.1355 (4)	0.5042 (5)	0.0476 (12)
H10	0.6651	0.1447	0.4223	0.057*
C11	0.7425 (5)	0.0378 (4)	0.5408 (5)	0.0595 (15)
H11	0.7356	−0.0183	0.4859	0.071*
C12	0.7965 (5)	0.0254 (4)	0.6618 (6)	0.0646 (16)
H12	0.8266	−0.0400	0.6882	0.077*
C13	0.8063 (5)	0.1080 (4)	0.7436 (5)	0.0548 (14)
H13	0.8445	0.0990	0.8242	0.066*
C14	0.7587 (4)	0.2053 (4)	0.7049 (4)	0.0427 (12)
C15	0.8242 (5)	0.2795 (5)	0.9067 (5)	0.0705 (18)
H15A	0.7862	0.2242	0.9488	0.106*
H15B	0.8173	0.3441	0.9505	0.106*
H15C	0.9103	0.2634	0.9035	0.106*
H2	0.667 (5)	0.404 (5)	0.6884 (9)	0.085*

	U11	U22	U33	U12	U13	U23
Cl1	0.0949 (10)	0.0518 (8)	0.0441 (7)	0.0028 (8)	−0.0130 (6)	0.0124 (6)
Cl2	0.0854 (10)	0.0383 (6)	0.0762 (10)	−0.0036 (7)	0.0194 (7)	−0.0199 (7)
N1	0.053 (2)	0.033 (2)	0.0301 (19)	0.0056 (18)	−0.0001 (17)	0.0040 (16)
N2	0.059 (3)	0.035 (2)	0.034 (2)	0.0087 (19)	−0.005 (2)	0.0070 (18)
O1	0.074 (2)	0.0319 (18)	0.0310 (17)	0.0013 (16)	−0.0010 (16)	−0.0017 (14)
O2	0.086 (3)	0.048 (2)	0.0353 (19)	0.0129 (19)	−0.0132 (18)	0.0007 (17)
O3	0.066 (2)	0.054 (2)	0.038 (2)	0.0143 (18)	−0.0076 (17)	0.0048 (17)
C1	0.041 (3)	0.033 (2)	0.032 (2)	−0.0051 (19)	0.005 (2)	0.0042 (19)
C2	0.055 (3)	0.038 (3)	0.037 (3)	−0.006 (2)	0.001 (2)	0.001 (2)
C3	0.052 (3)	0.030 (3)	0.057 (3)	−0.003 (2)	0.005 (2)	0.004 (2)
C4	0.054 (3)	0.032 (3)	0.051 (3)	−0.008 (2)	0.014 (3)	−0.007 (2)
C5	0.049 (3)	0.039 (3)	0.037 (3)	−0.002 (2)	0.003 (2)	−0.004 (2)
C6	0.042 (3)	0.032 (2)	0.034 (3)	0.000 (2)	0.006 (2)	0.0013 (19)
C7	0.051 (3)	0.043 (3)	0.032 (2)	−0.003 (2)	0.002 (2)	0.001 (2)
C8	0.040 (3)	0.035 (2)	0.037 (3)	0.002 (2)	0.000 (2)	0.003 (2)
C9	0.041 (3)	0.030 (3)	0.041 (3)	0.0035 (19)	0.007 (2)	0.0096 (19)
C10	0.053 (3)	0.040 (3)	0.051 (3)	−0.003 (2)	0.011 (2)	−0.001 (2)
C11	0.072 (4)	0.035 (3)	0.072 (4)	0.001 (2)	0.011 (3)	−0.003 (3)
C12	0.063 (4)	0.038 (3)	0.094 (5)	0.017 (3)	0.015 (3)	0.022 (3)
C13	0.056 (3)	0.055 (3)	0.054 (3)	0.010 (3)	0.008 (3)	0.024 (3)
C14	0.043 (3)	0.042 (3)	0.043 (3)	0.007 (2)	0.007 (2)	0.011 (2)
C15	0.070 (4)	0.096 (5)	0.042 (3)	0.020 (3)	−0.010 (3)	0.007 (3)

Cl1—C2	1.734 (5)	C5—H5	0.9300
Cl2—C4	1.741 (5)	C6—C7	1.465 (6)
N1—C7	1.268 (5)	C7—H7	0.9300
N1—N2	1.377 (5)	C8—C9	1.496 (6)
N2—C8	1.350 (5)	C9—C10	1.381 (6)
N2—H2	0.900 (7)	C9—C14	1.397 (6)
O1—C1	1.337 (5)	C10—C11	1.375 (7)
O1—H1	0.8200	C10—H10	0.9300
O2—C8	1.223 (5)	C11—C12	1.383 (8)
O3—C14	1.373 (6)	C11—H11	0.9300
O3—C15	1.420 (6)	C12—C13	1.376 (8)
C1—C2	1.396 (6)	C12—H12	0.9300
C1—C6	1.407 (5)	C13—C14	1.392 (6)
C2—C3	1.379 (7)	C13—H13	0.9300
C3—C4	1.380 (6)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.390 (6)	C15—H15C	0.9600
C5—C6	1.394 (6)
C7—N1—N2	120.5 (4)	O2—C8—N2	121.2 (4)
C8—N2—N1	117.2 (3)	O2—C8—C9	121.1 (4)
C8—N2—H2	127 (4)	N2—C8—C9	117.7 (4)
N1—N2—H2	116 (4)	C10—C9—C14	117.3 (4)
C1—O1—H1	109.5	C10—C9—C8	116.5 (4)
C14—O3—C15	119.8 (4)	C14—C9—C8	126.1 (4)
O1—C1—C2	119.4 (4)	C11—C10—C9	123.1 (5)
O1—C1—C6	123.0 (4)	C11—C10—H10	118.4
C2—C1—C6	117.6 (4)	C9—C10—H10	118.4
C3—C2—C1	122.5 (4)	C10—C11—C12	118.1 (5)
C3—C2—Cl1	119.3 (4)	C10—C11—H11	121.0
C1—C2—Cl1	118.2 (4)	C12—C11—H11	121.0
C2—C3—C4	118.6 (4)	C13—C12—C11	121.2 (5)
C2—C3—H3	120.7	C13—C12—H12	119.4
C4—C3—H3	120.7	C11—C12—H12	119.4
C3—C4—C5	121.4 (4)	C12—C13—C14	119.4 (5)
C3—C4—Cl2	118.9 (4)	C12—C13—H13	120.3
C5—C4—Cl2	119.6 (4)	C14—C13—H13	120.3
C4—C5—C6	119.2 (4)	O3—C14—C13	121.5 (4)
C4—C5—H5	120.4	O3—C14—C9	117.7 (4)
C6—C5—H5	120.4	C13—C14—C9	120.8 (5)
C5—C6—C1	120.7 (4)	O3—C15—H15A	109.5
C5—C6—C7	118.7 (4)	O3—C15—H15B	109.5
C1—C6—C7	120.6 (4)	H15A—C15—H15B	109.5
N1—C7—C6	118.3 (4)	O3—C15—H15C	109.5
N1—C7—H7	120.8	H15A—C15—H15C	109.5
C6—C7—H7	120.8	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.82	2.543 (4)	146
N2—H2···O3	0.90 (1)	2.02 (5)	2.624 (4)	123 (5)
N2—H2···O1i	0.90 (1)	2.63 (4)	3.271 (5)	129 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.82	2.543 (4)	146
N2—H2⋯O3	0.90 (1)	2.02 (5)	2.624 (4)	123 (5)
N2—H2⋯O1i	0.90 (1)	2.63 (4)	3.271 (5)	129 (5)

Symmetry code: (i) .