(E)-N'-(5-Bromo-2-hy-droxy-benzyl-idene)-3-methyl-benzohydrazide.

In the title mol-ecule, C(15)H(13)BrN(2)O(2), an intra-molecular O-H⋯N hydrogen bond influences the mol-ecular conformation; the two benzene rings form a dihedral angle of 13.6 (3)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains along the a axis and weak inter-molecular C-H⋯O hydrogen bonds further link these chains into layers parallel to the ac plane.

Related literature

For applications of hydrazone compounds, see: Hillmer et al. (2010 ▶); Raj et al. (2007 ▶). For the crystal structures of related hydrazone compounds, see: Vijayakumar et al. (2009 ▶); Liu & You (2010 ▶); Liu & Wang (2010 ▶). For related structures, see: Xu et al. (2009 ▶); Shafiq et al. (2009 ▶).

Experimental

Crystal data

C15H13BrN2O2

M = 333.18

Monoclinic,

a = 7.138 (3) Å

b = 27.404 (10) Å

c = 7.859 (3) Å

β = 112.297 (5)°

V = 1422.4 (9) Å3

Z = 4

Mo Kα radiation

μ = 2.89 mm−1

T = 298 K

0.13 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.705, T max = 0.761

6807 measured reflections

3045 independent reflections

1489 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.106

S = 0.99

3045 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.36 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 datablock(s) global, I. DOI: 10.1107/S1600536811025426/cv5119sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025426/cv5119Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025426/cv5119Isup3.cml

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

C15H13BrN2O2	F(000) = 672
Mr = 333.18	Dx = 1.556 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 983 reflections
a = 7.138 (3) Å	θ = 2.5–24.5°
b = 27.404 (10) Å	µ = 2.89 mm−1
c = 7.859 (3) Å	T = 298 K
β = 112.297 (5)°	Block, colourless
V = 1422.4 (9) Å3	0.13 × 0.10 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3045 independent reflections
Radiation source: fine-focus sealed tube	1489 reflections with I > 2σ(I)
graphite	Rint = 0.056
ω scans	θmax = 27.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→8
Tmin = 0.705, Tmax = 0.761	k = −29→35
6807 measured reflections	l = −7→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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0322P)2 + 0.1905P] where P = (Fo2 + 2Fc2)/3
3045 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.32 e Å−3
1 restraint	Δρmin = −0.36 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 > 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
Br1	0.82155 (9)	1.017416 (16)	0.22011 (7)	0.0691 (2)
N1	0.7539 (5)	0.78962 (11)	0.4049 (4)	0.0343 (8)
N2	0.7822 (5)	0.76007 (11)	0.5550 (4)	0.0354 (8)
O1	0.6966 (5)	0.80234 (9)	0.0601 (4)	0.0539 (9)
H1	0.7095	0.7865	0.1525	0.081*
O2	0.6037 (4)	0.69873 (9)	0.3697 (3)	0.0444 (8)
C1	0.7856 (6)	0.86760 (13)	0.2857 (5)	0.0313 (9)
C2	0.7363 (6)	0.85015 (13)	0.1057 (5)	0.0365 (10)
C3	0.7251 (7)	0.88254 (15)	−0.0339 (5)	0.0474 (12)
H3	0.6992	0.8709	−0.1518	0.057*
C4	0.7520 (7)	0.93154 (15)	0.0010 (6)	0.0498 (12)
H4	0.7406	0.9531	−0.0938	0.060*
C5	0.7957 (6)	0.94894 (14)	0.1761 (6)	0.0430 (11)
C6	0.8154 (6)	0.91721 (13)	0.3166 (5)	0.0386 (10)
H6	0.8496	0.9293	0.4352	0.046*
C7	0.8052 (6)	0.83446 (14)	0.4357 (5)	0.0358 (10)
H7	0.8558	0.8460	0.5559	0.043*
C8	0.7035 (6)	0.71426 (13)	0.5232 (5)	0.0327 (10)
C9	0.7491 (6)	0.68420 (13)	0.6938 (5)	0.0320 (10)
C10	0.7697 (6)	0.63410 (14)	0.6820 (5)	0.0367 (10)
H10	0.7537	0.6202	0.5694	0.044*
C11	0.8140 (6)	0.60430 (13)	0.8356 (6)	0.0386 (10)
C12	0.8309 (6)	0.62636 (16)	1.0002 (6)	0.0514 (12)
H12	0.8573	0.6069	1.1038	0.062*
C13	0.8099 (7)	0.67597 (16)	1.0153 (6)	0.0498 (12)
H13	0.8230	0.6897	1.1275	0.060*
C14	0.7689 (6)	0.70533 (14)	0.8605 (5)	0.0400 (11)
H14	0.7548	0.7389	0.8688	0.048*
C15	0.8392 (8)	0.55033 (15)	0.8246 (7)	0.0644 (14)
H15A	0.7782	0.5400	0.6987	0.097*
H15B	0.7747	0.5340	0.8959	0.097*
H15C	0.9808	0.5424	0.8722	0.097*
H2	0.879 (5)	0.7674 (15)	0.664 (3)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0954 (5)	0.0325 (3)	0.0780 (4)	0.0030 (3)	0.0314 (3)	0.0053 (2)
N1	0.038 (2)	0.0305 (18)	0.034 (2)	0.0021 (15)	0.0127 (17)	0.0075 (14)
N2	0.037 (2)	0.0333 (19)	0.0296 (19)	−0.0013 (16)	0.0062 (17)	0.0078 (15)
O1	0.084 (2)	0.0348 (17)	0.0420 (17)	−0.0091 (16)	0.0230 (18)	−0.0069 (13)
O2	0.054 (2)	0.0402 (17)	0.0278 (16)	−0.0026 (13)	0.0030 (15)	−0.0019 (12)
C1	0.028 (3)	0.034 (2)	0.035 (2)	0.0047 (18)	0.0148 (19)	0.0009 (18)
C2	0.036 (3)	0.031 (2)	0.040 (3)	0.0017 (18)	0.012 (2)	−0.0017 (19)
C3	0.067 (4)	0.046 (3)	0.031 (2)	−0.002 (2)	0.020 (2)	−0.001 (2)
C4	0.060 (3)	0.046 (3)	0.045 (3)	0.005 (2)	0.021 (3)	0.016 (2)
C5	0.047 (3)	0.028 (2)	0.053 (3)	0.0012 (19)	0.017 (2)	0.0012 (19)
C6	0.040 (3)	0.034 (2)	0.036 (2)	0.0017 (19)	0.009 (2)	0.0013 (19)
C7	0.035 (3)	0.035 (2)	0.034 (2)	0.0006 (19)	0.010 (2)	0.0022 (18)
C8	0.032 (3)	0.031 (2)	0.034 (2)	0.0023 (18)	0.011 (2)	0.0027 (18)
C9	0.032 (3)	0.032 (2)	0.029 (2)	−0.0009 (17)	0.008 (2)	0.0021 (17)
C10	0.034 (3)	0.037 (2)	0.037 (2)	0.0035 (18)	0.012 (2)	0.0017 (18)
C11	0.031 (3)	0.034 (2)	0.052 (3)	0.0041 (19)	0.016 (2)	0.009 (2)
C12	0.050 (3)	0.056 (3)	0.041 (3)	−0.008 (2)	0.010 (2)	0.018 (2)
C13	0.059 (3)	0.057 (3)	0.033 (3)	−0.010 (2)	0.017 (2)	−0.001 (2)
C14	0.047 (3)	0.035 (2)	0.038 (2)	−0.005 (2)	0.016 (2)	−0.0043 (19)
C15	0.073 (4)	0.039 (3)	0.084 (4)	0.003 (2)	0.033 (3)	0.014 (2)

Br1—C5	1.904 (4)	C6—H6	0.9300
N1—C7	1.279 (4)	C7—H7	0.9300
N1—N2	1.381 (4)	C8—C9	1.501 (5)
N2—C8	1.359 (4)	C9—C10	1.388 (5)
N2—H2	0.899 (10)	C9—C14	1.390 (5)
O1—C2	1.359 (4)	C10—C11	1.391 (5)
O1—H1	0.8200	C10—H10	0.9300
O2—C8	1.222 (4)	C11—C12	1.391 (5)
C1—C6	1.383 (5)	C11—C15	1.496 (5)
C1—C2	1.406 (5)	C12—C13	1.378 (6)
C1—C7	1.452 (5)	C12—H12	0.9300
C2—C3	1.390 (5)	C13—C14	1.394 (5)
C3—C4	1.369 (5)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.375 (5)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.371 (5)	C15—H15C	0.9600
C7—N1—N2	117.6 (3)	O2—C8—C9	122.6 (3)
C8—N2—N1	117.9 (3)	N2—C8—C9	114.1 (3)
C8—N2—H2	120 (3)	C10—C9—C14	120.0 (3)
N1—N2—H2	120 (3)	C10—C9—C8	118.4 (3)
C2—O1—H1	109.5	C14—C9—C8	121.6 (3)
C6—C1—C2	118.3 (3)	C9—C10—C11	121.2 (4)
C6—C1—C7	120.7 (3)	C9—C10—H10	119.4
C2—C1—C7	120.9 (3)	C11—C10—H10	119.4
O1—C2—C3	117.6 (4)	C10—C11—C12	117.6 (4)
O1—C2—C1	122.7 (3)	C10—C11—C15	121.5 (4)
C3—C2—C1	119.6 (3)	C12—C11—C15	120.9 (4)
C4—C3—C2	120.4 (4)	C13—C12—C11	122.4 (4)
C4—C3—H3	119.8	C13—C12—H12	118.8
C2—C3—H3	119.8	C11—C12—H12	118.8
C3—C4—C5	120.1 (4)	C12—C13—C14	119.2 (4)
C3—C4—H4	119.9	C12—C13—H13	120.4
C5—C4—H4	119.9	C14—C13—H13	120.4
C6—C5—C4	120.1 (4)	C9—C14—C13	119.7 (4)
C6—C5—Br1	120.4 (3)	C9—C14—H14	120.2
C4—C5—Br1	119.5 (3)	C13—C14—H14	120.2
C5—C6—C1	121.3 (4)	C11—C15—H15A	109.5
C5—C6—H6	119.3	C11—C15—H15B	109.5
C1—C6—H6	119.3	H15A—C15—H15B	109.5
N1—C7—C1	121.0 (3)	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	123.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.90 (1)	2.02 (2)	2.890 (4)	163 (4)
O1—H1···N1	0.82	1.89	2.605 (4)	146
C14—H14···O1ii	0.93	2.44	3.226 (4)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.90 (1)	2.02 (2)	2.890 (4)	163 (4)
O1—H1⋯N1	0.82	1.89	2.605 (4)	146
C14—H14⋯O1ii	0.93	2.44	3.226 (4)	143

Symmetry codes: (i) ; (ii) .