(E)-4-[(4-Bromo-benzyl-idene)amino]phenol.

In the title compound, C(13)H(10)BrNO, the dihedral angle between the benzene rings is 35.20 (8)°. In the crystal, mol-ecules are linked by O-H⋯N hydrogen bonds, forming a zigzag chain along the a axis. A weak C-H⋯π inter-action is observed between the chains.

Related literature

For the biological activity of benzyl­idene derivatives, see: El Masry et al. (2000 ▶); Fegade et al. (2009 ▶); Foroumadi et al. (2007 ▶); Hodnett & Dunn (1970 ▶); Hu & Zhou (2004 ▶); Jada et al. (2008 ▶); Samadhiya & Halve (2001 ▶); Singh & Dash (1988 ▶). For related structures, see: Cui et al. (2009 ▶); Sun et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H10BrNO

M = 276.13

Orthorhombic,

a = 12.7035 (4) Å

b = 10.3897 (3) Å

c = 17.0899 (6) Å

V = 2255.62 (12) Å3

Z = 8

Mo Kα radiation

μ = 3.62 mm−1

T = 295 K

0.20 × 0.16 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.503, T max = 0.581

13273 measured reflections

2670 independent reflections

1710 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.086

S = 1.00

2670 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680905538X/is2508sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905538X/is2508Isup2.hkl

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

C13H10BrNO	F(000) = 1104
Mr = 276.13	Dx = 1.626 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2371 reflections
a = 12.7035 (4) Å	θ = 2.4–23.7°
b = 10.3897 (3) Å	µ = 3.62 mm−1
c = 17.0899 (6) Å	T = 295 K
V = 2255.62 (12) Å3	Block, brown
Z = 8	0.20 × 0.16 × 0.15 mm

Bruker Kappa APEXII CCD diffractometer	2670 independent reflections
Radiation source: fine-focus sealed tube	1710 reflections with I > 2σ(I)
graphite	Rint = 0.043
ω and φ scans	θmax = 27.8°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→16
Tmin = 0.503, Tmax = 0.581	k = −12→13
13273 measured reflections	l = −22→22

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0358P)2 + 0.8359P] where P = (Fo2 + 2Fc2)/3
2670 reflections	(Δ/σ)max = 0.001
146 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.39 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.

	x	y	z	Uiso*/Ueq
C1	0.16600 (18)	0.0270 (2)	0.54592 (14)	0.0371 (6)
C2	0.2620 (2)	−0.0367 (3)	0.54384 (16)	0.0463 (7)
H2	0.2727	−0.1086	0.5753	0.056*
C3	0.34124 (19)	0.0056 (3)	0.49578 (18)	0.0520 (7)
H3	0.4054	−0.0374	0.4944	0.062*
C4	0.32501 (19)	0.1120 (3)	0.44968 (15)	0.0422 (6)
C5	0.2319 (2)	0.1769 (3)	0.45068 (16)	0.0463 (7)
H5	0.2220	0.2490	0.4192	0.056*
C6	0.1528 (2)	0.1340 (3)	0.49907 (16)	0.0449 (7)
H6	0.0891	0.1780	0.5002	0.054*
C7	0.07751 (18)	−0.0183 (3)	0.59347 (15)	0.0383 (6)
H7	0.0158	0.0298	0.5927	0.046*
C8	−0.01245 (17)	−0.1551 (2)	0.67752 (14)	0.0325 (5)
C9	−0.08369 (16)	−0.0690 (2)	0.70991 (15)	0.0365 (6)
H9	−0.0736	0.0189	0.7031	0.044*
C10	−0.16897 (17)	−0.1120 (2)	0.75198 (14)	0.0368 (6)
H10	−0.2155	−0.0532	0.7740	0.044*
C11	−0.18585 (16)	−0.2426 (2)	0.76165 (15)	0.0360 (6)
C12	−0.11568 (19)	−0.3294 (2)	0.72949 (16)	0.0412 (6)
H12	−0.1267	−0.4174	0.7355	0.049*
C13	−0.02907 (18)	−0.2855 (2)	0.68836 (15)	0.0388 (6)
H13	0.0186	−0.3443	0.6677	0.047*
N1	0.07946 (14)	−0.1183 (2)	0.63553 (12)	0.0367 (5)
O1	−0.26777 (13)	−0.29148 (18)	0.80295 (12)	0.0497 (5)
H1	−0.3015	−0.2324	0.8226	0.075*
Br1	0.43298 (2)	0.16639 (3)	0.38080 (2)	0.06483 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0383 (13)	0.0383 (15)	0.0348 (14)	−0.0034 (11)	−0.0019 (11)	−0.0038 (12)
C2	0.0458 (14)	0.0461 (16)	0.0471 (16)	0.0036 (12)	0.0056 (13)	0.0117 (14)
C3	0.0386 (14)	0.0573 (19)	0.0599 (19)	0.0045 (13)	0.0086 (14)	0.0115 (15)
C4	0.0427 (14)	0.0468 (16)	0.0371 (15)	−0.0113 (12)	0.0046 (12)	0.0009 (13)
C5	0.0549 (16)	0.0432 (16)	0.0407 (16)	−0.0024 (13)	0.0003 (13)	0.0081 (13)
C6	0.0406 (14)	0.0464 (17)	0.0476 (17)	0.0047 (11)	0.0009 (13)	0.0066 (13)
C7	0.0322 (13)	0.0420 (16)	0.0406 (14)	0.0007 (10)	−0.0006 (11)	−0.0023 (13)
C8	0.0268 (11)	0.0357 (14)	0.0349 (13)	−0.0010 (10)	−0.0028 (10)	0.0021 (11)
C9	0.0337 (12)	0.0305 (13)	0.0452 (16)	−0.0010 (10)	−0.0018 (11)	0.0006 (12)
C10	0.0332 (13)	0.0360 (15)	0.0411 (15)	0.0066 (10)	−0.0012 (11)	−0.0013 (12)
C11	0.0291 (12)	0.0387 (16)	0.0403 (15)	0.0004 (10)	0.0010 (11)	0.0041 (11)
C12	0.0361 (12)	0.0308 (14)	0.0566 (18)	0.0013 (11)	0.0019 (12)	0.0056 (13)
C13	0.0319 (12)	0.0364 (15)	0.0480 (16)	0.0076 (11)	0.0022 (11)	0.0021 (13)
N1	0.0314 (10)	0.0404 (12)	0.0384 (13)	−0.0021 (8)	0.0016 (9)	0.0000 (10)
O1	0.0371 (10)	0.0431 (11)	0.0688 (14)	0.0020 (8)	0.0169 (9)	0.0058 (10)
Br1	0.0582 (2)	0.0736 (3)	0.0627 (2)	−0.01461 (15)	0.01935 (16)	0.01033 (18)

C1—C6	1.380 (4)	C8—C13	1.383 (3)
C1—C2	1.388 (3)	C8—C9	1.388 (3)
C1—C7	1.465 (3)	C8—N1	1.423 (3)
C2—C3	1.371 (4)	C9—C10	1.375 (3)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.373 (4)	C10—C11	1.383 (4)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.362 (4)	C11—O1	1.356 (3)
C4—Br1	1.894 (2)	C11—C12	1.382 (3)
C5—C6	1.376 (4)	C12—C13	1.383 (3)
C5—H5	0.9300	C12—H12	0.9300
C6—H6	0.9300	C13—H13	0.9300
C7—N1	1.264 (3)	O1—H1	0.8200
C7—H7	0.9300
C6—C1—C2	118.4 (2)	C13—C8—C9	118.6 (2)
C6—C1—C7	119.2 (2)	C13—C8—N1	117.1 (2)
C2—C1—C7	122.4 (2)	C9—C8—N1	124.3 (2)
C3—C2—C1	120.5 (3)	C10—C9—C8	120.9 (2)
C3—C2—H2	119.8	C10—C9—H9	119.6
C1—C2—H2	119.8	C8—C9—H9	119.6
C2—C3—C4	119.4 (2)	C9—C10—C11	120.2 (2)
C2—C3—H3	120.3	C9—C10—H10	119.9
C4—C3—H3	120.3	C11—C10—H10	119.9
C5—C4—C3	121.5 (2)	O1—C11—C12	117.2 (2)
C5—C4—Br1	119.3 (2)	O1—C11—C10	123.3 (2)
C3—C4—Br1	119.2 (2)	C12—C11—C10	119.5 (2)
C4—C5—C6	118.7 (3)	C11—C12—C13	120.0 (2)
C4—C5—H5	120.6	C11—C12—H12	120.0
C6—C5—H5	120.6	C13—C12—H12	120.0
C5—C6—C1	121.4 (2)	C12—C13—C8	120.8 (2)
C5—C6—H6	119.3	C12—C13—H13	119.6
C1—C6—H6	119.3	C8—C13—H13	119.6
N1—C7—C1	124.4 (2)	C7—N1—C8	119.4 (2)
N1—C7—H7	117.8	C11—O1—H1	109.5
C1—C7—H7	117.8
C6—C1—C2—C3	−0.5 (4)	N1—C8—C9—C10	−177.8 (2)
C7—C1—C2—C3	177.0 (3)	C8—C9—C10—C11	−1.0 (4)
C1—C2—C3—C4	0.1 (5)	C9—C10—C11—O1	179.4 (2)
C2—C3—C4—C5	0.2 (5)	C9—C10—C11—C12	0.8 (4)
C2—C3—C4—Br1	−177.9 (2)	O1—C11—C12—C13	−178.4 (2)
C3—C4—C5—C6	−0.1 (4)	C10—C11—C12—C13	0.3 (4)
Br1—C4—C5—C6	177.9 (2)	C11—C12—C13—C8	−1.2 (4)
C4—C5—C6—C1	−0.2 (4)	C9—C8—C13—C12	1.0 (4)
C2—C1—C6—C5	0.5 (4)	N1—C8—C13—C12	179.1 (2)
C7—C1—C6—C5	−177.0 (3)	C1—C7—N1—C8	−178.2 (2)
C6—C1—C7—N1	176.6 (3)	C13—C8—N1—C7	147.6 (3)
C2—C1—C7—N1	−0.9 (4)	C9—C8—N1—C7	−34.5 (4)
C13—C8—C9—C10	0.1 (4)

Cg1 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	2.05	2.848 (3)	164
C5—H5···Cg1ii	0.93	2.89	3.374 (3)	114

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	2.05	2.848 (3)	164
C5—H5⋯Cg1ii	0.93	2.89	3.374 (3)	114

Symmetry codes: (i) ; (ii) .