(E)-N'-[1-(4-Bromo-phen-yl)ethyl-idene]-2-hydroxy-benzohydrazide.

In the title compound, C(15)H(13)BrN(2)O(2), the two aromatic rings form a dihedral angle of 7.9 (1)° and an intra-molecular N-H⋯O hydrogen bond influences the mol-ecular conformation. In the crystal, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into chains propagated in [001]. The crystal packing exhibits also π-π inter-actions, which pair mol-ecules into centrosymmetric dimers with short inter-molecular distances of 3.671 (4) Å between the centroids of aromatic rings.

Related literature

For the biological properties of Schiff base ligands, see: Jeewoth et al. (1999 ▶). For related structures, see: Fun et al. (2008 ▶); Cui et al. (2009 ▶); Nie (2008 ▶).

Experimental

Crystal data

C15H13BrN2O2

M = 333.18

Monoclinic,

a = 27.805 (3) Å

b = 7.9061 (9) Å

c = 13.5002 (15) Å

β = 113.344 (2)°

V = 2724.8 (5) Å3

Z = 8

Mo Kα radiation

μ = 3.02 mm−1

T = 298 K

0.39 × 0.14 × 0.12 mm

Data collection

Siemens SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.386, T max = 0.713

6480 measured reflections

2397 independent reflections

1602 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.111

S = 0.95

2397 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.74 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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 I, global. DOI: 10.1107/S1600536809042081/cv2623sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042081/cv2623Isup2.hkl

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

C15H13BrN2O2	F(000) = 1344
Mr = 333.18	Dx = 1.624 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 27.805 (3) Å	Cell parameters from 1955 reflections
b = 7.9061 (9) Å	θ = 2.7–26.0°
c = 13.5002 (15) Å	µ = 3.02 mm−1
β = 113.344 (2)°	T = 298 K
V = 2724.8 (5) Å3	Block, colourless
Z = 8	0.39 × 0.14 × 0.12 mm

Siemens SMART APEX CCD area-detector diffractometer	2397 independent reflections
Radiation source: fine-focus sealed tube	1602 reflections with I > 2σ(I)
graphite	Rint = 0.071
phi and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −32→32
Tmin = 0.386, Tmax = 0.713	k = −5→9
6480 measured reflections	l = −16→14

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) = 0.111	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0507P)2] where P = (Fo2 + 2Fc2)/3
2397 reflections	(Δ/σ)max = 0.002
181 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.74 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
Br1	1.171700 (16)	1.05278 (6)	1.41157 (3)	0.0585 (2)
N1	0.92749 (11)	0.6137 (4)	0.9225 (2)	0.0342 (8)
H1	0.9291	0.6170	0.8602	0.041*
N2	0.96688 (11)	0.6843 (4)	1.0103 (2)	0.0325 (7)
O1	0.88354 (11)	0.5298 (4)	1.02232 (19)	0.0555 (9)
O2	0.88245 (10)	0.5567 (4)	0.71317 (18)	0.0434 (7)
H2	0.8821	0.5286	0.6545	0.065*
C1	0.88626 (13)	0.5393 (5)	0.9337 (3)	0.0329 (9)
C2	0.84455 (14)	0.4681 (5)	0.8353 (3)	0.0317 (9)
C3	0.84277 (13)	0.4765 (5)	0.7298 (3)	0.0325 (9)
C4	0.80124 (15)	0.4043 (6)	0.6450 (3)	0.0450 (11)
H4	0.7998	0.4127	0.5752	0.054*
C5	0.76224 (15)	0.3206 (6)	0.6629 (3)	0.0467 (11)
H5	0.7347	0.2722	0.6053	0.056*
C6	0.76374 (15)	0.3079 (5)	0.7662 (3)	0.0461 (11)
H6	0.7376	0.2496	0.7787	0.055*
C7	0.80399 (14)	0.3818 (5)	0.8496 (3)	0.0394 (10)
H7	0.8044	0.3744	0.9187	0.047*
C8	1.01117 (15)	0.7562 (6)	0.8889 (3)	0.0453 (11)
H8A	1.0056	0.6454	0.8573	0.068*
H8B	1.0457	0.7943	0.9003	0.068*
H8C	0.9858	0.8331	0.8413	0.068*
C9	1.00561 (13)	0.7498 (5)	0.9952 (2)	0.0314 (9)
C10	1.04721 (13)	0.8237 (5)	1.0939 (3)	0.0312 (9)
C11	1.04697 (14)	0.7866 (5)	1.1949 (3)	0.0387 (10)
H11	1.0216	0.7137	1.1993	0.046*
C12	1.08322 (15)	0.8551 (6)	1.2876 (3)	0.0441 (10)
H12	1.0822	0.8297	1.3540	0.053*
C13	1.12116 (14)	0.9617 (5)	1.2819 (3)	0.0376 (9)
C14	1.12300 (16)	0.9996 (6)	1.1834 (3)	0.0446 (10)
H14	1.1487	1.0713	1.1795	0.054*
C15	1.08594 (14)	0.9290 (5)	1.0911 (3)	0.0393 (10)
H15	1.0873	0.9537	1.0248	0.047*

	U11	U22	U33	U12	U13	U23
Br1	0.0516 (3)	0.0628 (4)	0.0480 (3)	−0.0060 (3)	0.0059 (2)	−0.0110 (2)
N1	0.0355 (17)	0.045 (2)	0.0228 (15)	0.0001 (16)	0.0125 (13)	−0.0005 (14)
N2	0.0320 (17)	0.039 (2)	0.0259 (16)	0.0008 (15)	0.0105 (14)	−0.0028 (14)
O1	0.0562 (18)	0.088 (3)	0.0281 (14)	−0.0174 (17)	0.0231 (13)	−0.0038 (15)
O2	0.0502 (16)	0.060 (2)	0.0236 (12)	−0.0083 (15)	0.0181 (12)	−0.0062 (12)
C1	0.036 (2)	0.038 (2)	0.0268 (19)	0.0080 (19)	0.0146 (16)	0.0022 (17)
C2	0.0311 (19)	0.032 (2)	0.0301 (19)	0.0081 (18)	0.0104 (16)	0.0016 (17)
C3	0.034 (2)	0.035 (2)	0.0305 (19)	0.0059 (18)	0.0151 (17)	0.0000 (17)
C4	0.050 (3)	0.054 (3)	0.027 (2)	0.003 (2)	0.0108 (19)	−0.0065 (19)
C5	0.034 (2)	0.048 (3)	0.048 (2)	−0.001 (2)	0.0052 (19)	−0.009 (2)
C6	0.038 (2)	0.049 (3)	0.053 (3)	−0.002 (2)	0.020 (2)	−0.002 (2)
C7	0.037 (2)	0.044 (3)	0.036 (2)	0.001 (2)	0.0145 (18)	0.0041 (19)
C8	0.048 (2)	0.054 (3)	0.039 (2)	−0.003 (2)	0.0221 (19)	−0.005 (2)
C9	0.037 (2)	0.032 (2)	0.0277 (19)	0.0079 (18)	0.0145 (17)	0.0014 (16)
C10	0.031 (2)	0.031 (2)	0.0338 (19)	0.0078 (18)	0.0158 (16)	0.0012 (17)
C11	0.040 (2)	0.044 (3)	0.035 (2)	−0.005 (2)	0.0175 (18)	−0.0008 (19)
C12	0.051 (2)	0.052 (3)	0.030 (2)	0.004 (2)	0.0164 (19)	0.0058 (19)
C13	0.032 (2)	0.036 (2)	0.041 (2)	0.0022 (19)	0.0106 (17)	−0.0046 (18)
C14	0.042 (2)	0.043 (3)	0.049 (2)	−0.005 (2)	0.018 (2)	−0.001 (2)
C15	0.043 (2)	0.044 (3)	0.036 (2)	0.000 (2)	0.0210 (18)	0.0068 (19)

Br1—C13	1.899 (4)	C6—H6	0.9300
N1—C1	1.349 (5)	C7—H7	0.9300
N1—N2	1.374 (4)	C8—C9	1.504 (4)
N1—H1	0.8600	C8—H8A	0.9600
N2—C9	1.282 (4)	C8—H8B	0.9600
O1—C1	1.231 (4)	C8—H8C	0.9600
O2—C3	1.366 (4)	C9—C10	1.494 (5)
O2—H2	0.8200	C10—C15	1.374 (5)
C1—C2	1.485 (5)	C10—C11	1.398 (5)
C2—C7	1.395 (5)	C11—C12	1.369 (5)
C2—C3	1.407 (5)	C11—H11	0.9300
C3—C4	1.386 (5)	C12—C13	1.376 (5)
C4—C5	1.371 (5)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.384 (5)
C5—C6	1.383 (5)	C14—C15	1.382 (5)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.365 (5)	C15—H15	0.9300
C1—N1—N2	120.2 (3)	C9—C8—H8B	109.5
C1—N1—H1	119.9	H8A—C8—H8B	109.5
N2—N1—H1	119.9	C9—C8—H8C	109.5
C9—N2—N1	117.3 (3)	H8A—C8—H8C	109.5
C3—O2—H2	109.5	H8B—C8—H8C	109.5
O1—C1—N1	121.2 (3)	N2—C9—C10	114.8 (3)
O1—C1—C2	121.3 (3)	N2—C9—C8	125.2 (3)
N1—C1—C2	117.6 (3)	C10—C9—C8	120.1 (3)
C7—C2—C3	117.2 (3)	C15—C10—C11	117.5 (3)
C7—C2—C1	116.7 (3)	C15—C10—C9	123.4 (3)
C3—C2—C1	126.1 (3)	C11—C10—C9	119.1 (3)
O2—C3—C4	121.2 (3)	C12—C11—C10	121.5 (4)
O2—C3—C2	118.8 (3)	C12—C11—H11	119.3
C4—C3—C2	120.0 (3)	C10—C11—H11	119.3
C5—C4—C3	120.8 (3)	C11—C12—C13	119.7 (3)
C5—C4—H4	119.6	C11—C12—H12	120.2
C3—C4—H4	119.6	C13—C12—H12	120.2
C4—C5—C6	120.2 (4)	C12—C13—C14	120.5 (3)
C4—C5—H5	119.9	C12—C13—Br1	119.0 (3)
C6—C5—H5	119.9	C14—C13—Br1	120.5 (3)
C7—C6—C5	119.2 (4)	C15—C14—C13	118.8 (4)
C7—C6—H6	120.4	C15—C14—H14	120.6
C5—C6—H6	120.4	C13—C14—H14	120.6
C6—C7—C2	122.6 (3)	C10—C15—C14	122.2 (3)
C6—C7—H7	118.7	C10—C15—H15	118.9
C2—C7—H7	118.7	C14—C15—H15	118.9
C9—C8—H8A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.95	2.637 (3)	136
O2—H2···O1i	0.82	1.86	2.677 (3)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	1.95	2.637 (3)	136
O2—H2⋯O1i	0.82	1.86	2.677 (3)	178

Symmetry code: (i) .