N'-(3-Bromo-5-chloro-2-hydroxy-benzyl-idene)-2-methoxy-benzohydrazide.

The title compound, C(15)H(12)BrClN(2)O(3), was obtained by the condensation reaction between 3-bromo-5-chloro-2-hydroxy-benzaldehyde and 2-methoxy-benzohydrazide. The mol-ecule is essentially planar, with a dihedral angle between the two benzene rings of 4.7 (2)°, and displays an E configuration about the C=N double bond. The mol-ecular conformation is stabilized by intramolecular O-H⋯N and N-H⋯O hydrogen bonds. In the crystal structure, mol-ecules are linked into zigzag chains running parallel to the c axis by inter-molecular C-H⋯O hydrogen bonds. The chains are further connected through aromatic π-π stacking inter-actions with centroid-centroid distances of 3.583 (4) Å.

Related literature

For the biological properties of hydrazone compounds, see: Cukurovali et al. (2006 ▶); Karthikeyan et al. (2006 ▶); Kucukguzel et al. (2006 ▶). For the crystal structures of related hydrazone compounds, see: Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Zhang et al. (2009 ▶); Khaledi et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H12BrClN2O3

M = 383.63

Monoclinic,

a = 10.883 (1) Å

b = 12.863 (2) Å

c = 10.950 (1) Å

β = 96.027 (3)°

V = 1524.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.89 mm−1

T = 298 K

0.12 × 0.12 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.709, T max = 0.746

4397 measured reflections

2323 independent reflections

1906 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.062

S = 1.02

2323 reflections

205 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶), 671 Friedel pairs

Flack parameter: 0.068 (12)

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/S1600536809010198/rz2301sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010198/rz2301Isup2.hkl

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

C15H12BrClN2O3	F(000) = 768
Mr = 383.63	Dx = 1.672 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1920 reflections
a = 10.883 (1) Å	θ = 2.4–25.0°
b = 12.863 (2) Å	µ = 2.89 mm−1
c = 10.950 (1) Å	T = 298 K
β = 96.027 (3)°	Block, yellow
V = 1524.4 (3) Å3	0.12 × 0.12 × 0.10 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	2323 independent reflections
Radiation source: fine-focus sealed tube	1906 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans	θmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.709, Tmax = 0.746	k = −16→16
4397 measured reflections	l = −13→13

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.062	w = 1/[σ2(Fo2) + (0.0041P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2323 reflections	Δρmax = 0.32 e Å−3
205 parameters	Δρmin = −0.28 e Å−3
3 restraints	Absolute structure: Flack (1983), 671 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.068 (12)

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
Br1	0.87674 (5)	1.27290 (3)	0.55418 (4)	0.05914 (15)
Cl1	0.79439 (11)	1.45929 (8)	0.10011 (11)	0.0630 (3)
O3	0.5131 (3)	0.7894 (2)	−0.0042 (3)	0.0538 (9)
O2	0.6516 (3)	0.8295 (2)	0.3590 (3)	0.0546 (9)
C8	0.6188 (3)	0.8209 (3)	0.2494 (4)	0.0396 (9)
N2	0.6245 (3)	0.9033 (2)	0.1728 (3)	0.0418 (8)
N1	0.6674 (3)	0.9949 (2)	0.2236 (3)	0.0392 (7)
O1	0.7599 (3)	1.09258 (19)	0.4140 (2)	0.0444 (6)
H1	0.7332	1.0421	0.3738	0.067*
C7	0.6737 (3)	1.0742 (3)	0.1564 (4)	0.0415 (9)
H7	0.6477	1.0713	0.0728	0.050*
C2	0.7652 (3)	1.1748 (3)	0.3396 (3)	0.0344 (8)
C6	0.7306 (4)	1.2597 (3)	0.1403 (5)	0.0390 (11)
H6	0.7025	1.2577	0.0571	0.047*
C9	0.5699 (4)	0.7207 (3)	0.1948 (4)	0.0383 (9)
C1	0.7228 (3)	1.1710 (3)	0.2134 (3)	0.0370 (9)
C5	0.7799 (3)	1.3492 (3)	0.1920 (4)	0.0447 (10)
C3	0.8145 (3)	1.2676 (3)	0.3864 (4)	0.0420 (9)
C4	0.8216 (4)	1.3547 (3)	0.3147 (4)	0.0444 (10)
H4	0.8541	1.4163	0.3487	0.053*
C10	0.5176 (3)	0.7058 (3)	0.0733 (4)	0.0433 (10)
C11	0.4706 (4)	0.6082 (3)	0.0378 (4)	0.0528 (11)
H11	0.4330	0.5987	−0.0417	0.063*
C15	0.4532 (5)	0.7794 (4)	−0.1255 (4)	0.0696 (15)
H15A	0.3678	0.7624	−0.1219	0.104*
H15B	0.4922	0.7252	−0.1678	0.104*
H15C	0.4593	0.8438	−0.1687	0.104*
C14	0.5754 (4)	0.6344 (4)	0.2755 (4)	0.0486 (12)
H14	0.6094	0.6422	0.3565	0.058*
C13	0.5317 (4)	0.5407 (4)	0.2359 (5)	0.0645 (13)
H13	0.5374	0.4845	0.2896	0.077*
C12	0.4787 (4)	0.5271 (4)	0.1169 (5)	0.0661 (13)
H12	0.4485	0.4622	0.0911	0.079*
H2	0.597 (4)	0.897 (4)	0.0932 (14)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0772 (3)	0.0527 (2)	0.0443 (2)	−0.0058 (3)	−0.00881 (19)	−0.0139 (3)
Cl1	0.0775 (8)	0.0393 (6)	0.0743 (8)	0.0053 (5)	0.0180 (6)	0.0199 (6)
O3	0.066 (2)	0.059 (2)	0.0339 (18)	−0.0160 (16)	−0.0040 (16)	−0.0048 (16)
O2	0.080 (2)	0.049 (2)	0.0320 (18)	−0.0123 (16)	−0.0084 (16)	−0.0009 (14)
C8	0.041 (2)	0.038 (2)	0.040 (2)	0.0012 (17)	0.0042 (18)	−0.0006 (19)
N2	0.058 (2)	0.0367 (19)	0.0294 (17)	−0.0104 (15)	−0.0027 (15)	−0.0052 (15)
N1	0.0491 (18)	0.0338 (18)	0.0338 (17)	−0.0084 (14)	0.0003 (14)	−0.0040 (14)
O1	0.0669 (17)	0.0337 (16)	0.0304 (14)	−0.0053 (13)	−0.0056 (13)	−0.0023 (12)
C7	0.049 (2)	0.044 (2)	0.031 (2)	0.0010 (18)	−0.0001 (17)	−0.0006 (18)
C2	0.041 (2)	0.028 (2)	0.034 (2)	0.0049 (15)	0.0012 (17)	−0.0020 (16)
C6	0.042 (2)	0.037 (3)	0.038 (3)	0.0041 (18)	0.0027 (19)	0.0063 (18)
C9	0.040 (2)	0.036 (2)	0.041 (2)	−0.0012 (16)	0.0115 (18)	−0.0041 (18)
C1	0.0378 (19)	0.037 (2)	0.036 (2)	0.0046 (17)	0.0020 (17)	−0.0033 (17)
C5	0.045 (2)	0.031 (2)	0.059 (3)	0.0068 (18)	0.013 (2)	0.006 (2)
C3	0.045 (2)	0.045 (2)	0.035 (2)	0.0050 (18)	−0.0012 (18)	−0.0095 (19)
C4	0.050 (2)	0.029 (2)	0.055 (3)	0.0033 (16)	0.008 (2)	−0.0042 (18)
C10	0.038 (2)	0.050 (3)	0.043 (2)	−0.0062 (17)	0.0095 (18)	−0.0154 (19)
C11	0.053 (3)	0.052 (3)	0.055 (3)	−0.015 (2)	0.012 (2)	−0.018 (2)
C15	0.073 (3)	0.089 (4)	0.044 (3)	−0.023 (3)	−0.005 (2)	−0.011 (3)
C14	0.045 (2)	0.052 (3)	0.049 (3)	−0.006 (2)	0.008 (2)	−0.010 (2)
C13	0.071 (3)	0.043 (3)	0.083 (4)	−0.004 (2)	0.025 (3)	0.012 (3)
C12	0.067 (3)	0.044 (3)	0.090 (4)	−0.014 (2)	0.020 (3)	−0.018 (3)

Br1—C3	1.891 (4)	C6—H6	0.9300
Cl1—C5	1.754 (4)	C9—C10	1.404 (6)
O3—C10	1.367 (5)	C9—C14	1.417 (6)
O3—C15	1.423 (5)	C5—C4	1.374 (6)
O2—C8	1.221 (4)	C3—C4	1.375 (6)
C8—N2	1.357 (5)	C4—H4	0.9300
C8—C9	1.494 (5)	C10—C11	1.396 (5)
N2—N1	1.364 (4)	C11—C12	1.353 (7)
N2—H2	0.895 (10)	C11—H11	0.9300
N1—C7	1.265 (4)	C15—H15A	0.9600
O1—C2	1.341 (4)	C15—H15B	0.9600
O1—H1	0.8200	C15—H15C	0.9600
C7—C1	1.468 (5)	C14—C13	1.350 (6)
C7—H7	0.9300	C14—H14	0.9300
C2—C3	1.384 (5)	C13—C12	1.379 (7)
C2—C1	1.411 (5)	C13—H13	0.9300
C6—C5	1.367 (6)	C12—H12	0.9300
C6—C1	1.402 (6)
C10—O3—C15	119.4 (4)	C4—C3—C2	122.2 (4)
O2—C8—N2	120.6 (4)	C4—C3—Br1	119.3 (3)
O2—C8—C9	121.8 (4)	C2—C3—Br1	118.5 (3)
N2—C8—C9	117.6 (4)	C5—C4—C3	118.9 (4)
C8—N2—N1	117.3 (3)	C5—C4—H4	120.5
C8—N2—H2	120 (3)	C3—C4—H4	120.5
N1—N2—H2	123 (3)	O3—C10—C11	123.1 (4)
C7—N1—N2	119.8 (3)	O3—C10—C9	117.7 (3)
C2—O1—H1	109.5	C11—C10—C9	119.1 (4)
N1—C7—C1	118.4 (3)	C12—C11—C10	121.2 (4)
N1—C7—H7	120.8	C12—C11—H11	119.4
C1—C7—H7	120.8	C10—C11—H11	119.4
O1—C2—C3	119.6 (3)	O3—C15—H15A	109.5
O1—C2—C1	122.5 (3)	O3—C15—H15B	109.5
C3—C2—C1	117.9 (3)	H15A—C15—H15B	109.5
C5—C6—C1	119.6 (4)	O3—C15—H15C	109.5
C5—C6—H6	120.2	H15A—C15—H15C	109.5
C1—C6—H6	120.2	H15B—C15—H15C	109.5
C10—C9—C14	118.1 (4)	C13—C14—C9	120.6 (4)
C10—C9—C8	126.1 (4)	C13—C14—H14	119.7
C14—C9—C8	115.9 (4)	C9—C14—H14	119.7
C6—C1—C2	119.8 (4)	C14—C13—C12	121.0 (5)
C6—C1—C7	119.3 (4)	C14—C13—H13	119.5
C2—C1—C7	120.9 (3)	C12—C13—H13	119.5
C6—C5—C4	121.5 (4)	C11—C12—C13	119.9 (4)
C6—C5—Cl1	119.8 (4)	C11—C12—H12	120.0
C4—C5—Cl1	118.6 (3)	C13—C12—H12	120.0

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.83	2.549 (4)	146
N2—H2···O3	0.90 (1)	1.92 (3)	2.623 (4)	134 (4)
C6—H6···O2i	0.93	2.45	3.315 (6)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.83	2.549 (4)	146
N2—H2⋯O3	0.895 (10)	1.92 (3)	2.623 (4)	134 (4)
C6—H6⋯O2i	0.93	2.45	3.315 (6)	154

Symmetry code: (i) .