2-[(1,3-Benzothia-zol-2-yl)imino-meth-yl]-4-bromo-phenol.

In the title compound, C(14)H(9)BrN(2)OS, the dihedral angle between the benzene rings is 3.1 (3)°. An intra-molecular O-H⋯N(imine) hydrogen bond occurs. The crystal structure is stabilized by weak inter-molecular C-H⋯O inter-actions.

Related literature

For the uses of Schiff bases, see: Da Silva et al. (2011 ▶); Dhar & Taploo (1982 ▶); Przybylski et al. (2009 ▶); Guo et al. (2007 ▶); Bringmann et al. (2004 ▶). For the structures of closely related imines, see: Liu et al. (2009 ▶); Asiri et al. (2010 ▶).

Experimental

Crystal data

C14H9BrN2OS

M = 333.20

Monoclinic,

a = 26.1607 (2) Å

b = 4.0565 (2) Å

c = 12.1435 (3) Å

β = 91.5720 (1)°

V = 1288.19 (7) Å3

Z = 4

Mo Kα radiation

μ = 3.34 mm−1

T = 296 K

0.45 × 0.40 × 0.38 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.242, T max = 0.281

11848 measured reflections

2232 independent reflections

1466 reflections with I > 2σ(I)

R int = 0.138

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.118

S = 0.93

2232 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.54 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 datablocks I, global. DOI: 10.1107/S160053681101275X/bh2345sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101275X/bh2345Isup2.hkl

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

C14H9BrN2OS	Z = 4
Mr = 333.20	F(000) = 664
Monoclinic, P21/c	Dx = 1.718 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 26.1607 (2) Å	θ = 3.4–21.4°
b = 4.0565 (2) Å	µ = 3.34 mm−1
c = 12.1435 (3) Å	T = 296 K
β = 91.5720 (1)°	Block, yellow
V = 1288.19 (7) Å3	0.45 × 0.40 × 0.38 mm

Bruker SMART APEX CCD area-detector diffractometer	2232 independent reflections
Radiation source: fine-focus sealed tube	1466 reflections with I > 2σ(I)
graphite	Rint = 0.138
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −30→30
Tmin = 0.242, Tmax = 0.281	k = −4→4
11848 measured reflections	l = −14→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) = 0.118	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3
2232 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.54 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Br1	0.03658 (2)	1.69312 (15)	0.65038 (5)	0.0536 (2)
S2	0.29866 (5)	0.7609 (3)	0.70906 (12)	0.0488 (4)
C1	0.17288 (19)	1.3148 (12)	0.5361 (4)	0.0370 (11)
O1	0.20795 (15)	1.3280 (10)	0.3543 (3)	0.0582 (10)
H1	0.2300	1.2208	0.3877	0.087*
C12	0.4377 (2)	0.3239 (15)	0.7216 (6)	0.0633 (17)
H12	0.4606	0.2193	0.7700	0.076*
C4	0.0898 (2)	1.6691 (13)	0.4506 (4)	0.0458 (13)
H4	0.0620	1.7888	0.4225	0.055*
C6	0.13249 (18)	1.4049 (11)	0.6017 (4)	0.0372 (12)
H6	0.1335	1.3473	0.6758	0.045*
N2	0.33356 (16)	0.7896 (11)	0.5088 (4)	0.0471 (11)
N1	0.25338 (15)	1.0410 (11)	0.5215 (3)	0.0432 (10)
C2	0.17096 (19)	1.4091 (12)	0.4229 (4)	0.0399 (12)
C8	0.29517 (19)	0.8711 (13)	0.5676 (4)	0.0437 (13)
C5	0.09127 (19)	1.5761 (12)	0.5601 (4)	0.0381 (12)
C7	0.21554 (18)	1.1329 (12)	0.5801 (4)	0.0386 (12)
H7	0.2160	1.0782	0.6545	0.046*
C9	0.3704 (2)	0.6300 (13)	0.5745 (5)	0.0469 (14)
C3	0.1294 (2)	1.5847 (13)	0.3824 (4)	0.0501 (14)
H3	0.1279	1.6472	0.3087	0.060*
C11	0.3918 (2)	0.4411 (14)	0.7602 (5)	0.0596 (16)
H11	0.3837	0.4206	0.8340	0.071*
C10	0.35821 (19)	0.5906 (12)	0.6847 (4)	0.0432 (13)
C13	0.4499 (2)	0.3597 (14)	0.6131 (6)	0.0653 (18)
H13	0.4812	0.2816	0.5897	0.078*
C14	0.4168 (2)	0.5088 (15)	0.5376 (5)	0.0581 (16)
H14	0.4253	0.5279	0.4640	0.070*

	U11	U22	U33	U12	U13	U23
Br1	0.0431 (3)	0.0658 (4)	0.0521 (4)	0.0039 (3)	0.0053 (2)	−0.0054 (3)
S2	0.0435 (8)	0.0614 (9)	0.0415 (8)	0.0046 (6)	0.0040 (6)	0.0028 (7)
C1	0.046 (3)	0.041 (3)	0.023 (3)	−0.001 (2)	−0.005 (2)	−0.003 (2)
O1	0.058 (2)	0.089 (3)	0.0284 (19)	0.013 (2)	0.0052 (18)	0.008 (2)
C12	0.046 (4)	0.064 (4)	0.080 (5)	0.001 (3)	−0.003 (3)	0.010 (4)
C4	0.043 (3)	0.050 (3)	0.044 (3)	−0.001 (3)	−0.010 (3)	−0.001 (3)
C6	0.042 (3)	0.045 (3)	0.025 (3)	−0.006 (2)	0.001 (2)	−0.004 (2)
N2	0.043 (3)	0.060 (3)	0.039 (3)	−0.004 (2)	0.002 (2)	−0.005 (2)
N1	0.040 (2)	0.054 (3)	0.036 (2)	−0.006 (2)	0.001 (2)	−0.004 (2)
C2	0.043 (3)	0.050 (3)	0.027 (3)	−0.007 (2)	0.001 (2)	−0.003 (2)
C8	0.039 (3)	0.054 (3)	0.038 (3)	−0.005 (3)	0.005 (2)	−0.004 (3)
C5	0.042 (3)	0.038 (3)	0.034 (3)	−0.003 (2)	−0.003 (2)	−0.002 (2)
C7	0.044 (3)	0.050 (3)	0.021 (3)	−0.008 (2)	−0.003 (2)	0.002 (2)
C9	0.039 (3)	0.050 (3)	0.052 (3)	−0.008 (3)	0.003 (3)	−0.004 (3)
C3	0.056 (4)	0.067 (4)	0.027 (3)	0.003 (3)	−0.007 (3)	0.005 (3)
C11	0.054 (4)	0.065 (4)	0.060 (4)	−0.001 (3)	−0.003 (3)	0.004 (3)
C10	0.036 (3)	0.043 (3)	0.051 (3)	−0.006 (2)	0.002 (3)	−0.002 (3)
C13	0.042 (3)	0.060 (4)	0.094 (5)	0.002 (3)	0.006 (4)	−0.012 (4)
C14	0.051 (4)	0.065 (4)	0.059 (4)	−0.008 (3)	0.012 (3)	−0.011 (3)

Br1—C5	1.887 (5)	C6—H6	0.9300
S2—C10	1.737 (5)	N2—C8	1.291 (6)
S2—C8	1.775 (5)	N2—C9	1.393 (7)
C1—C6	1.390 (6)	N1—C7	1.290 (6)
C1—C2	1.426 (6)	N1—C8	1.396 (6)
C1—C7	1.430 (7)	C2—C3	1.380 (7)
O1—C2	1.335 (5)	C7—H7	0.9300
O1—H1	0.8200	C9—C10	1.393 (7)
C12—C13	1.372 (9)	C9—C14	1.395 (7)
C12—C11	1.384 (8)	C3—H3	0.9300
C12—H12	0.9300	C11—C10	1.392 (7)
C4—C5	1.382 (7)	C11—H11	0.9300
C4—C3	1.387 (7)	C13—C14	1.382 (8)
C4—H4	0.9300	C13—H13	0.9300
C6—C5	1.367 (6)	C14—H14	0.9300
C10—S2—C8	87.6 (2)	C6—C5—Br1	121.1 (4)
C6—C1—C2	118.3 (5)	C4—C5—Br1	119.2 (4)
C6—C1—C7	121.3 (4)	N1—C7—C1	123.1 (4)
C2—C1—C7	120.4 (4)	N1—C7—H7	118.5
C2—O1—H1	109.5	C1—C7—H7	118.5
C13—C12—C11	121.0 (6)	C10—C9—N2	115.5 (5)
C13—C12—H12	119.5	C10—C9—C14	119.5 (6)
C11—C12—H12	119.5	N2—C9—C14	125.0 (5)
C5—C4—C3	120.3 (5)	C2—C3—C4	120.6 (5)
C5—C4—H4	119.8	C2—C3—H3	119.7
C3—C4—H4	119.8	C4—C3—H3	119.7
C5—C6—C1	121.8 (5)	C12—C11—C10	117.7 (6)
C5—C6—H6	119.1	C12—C11—H11	121.2
C1—C6—H6	119.1	C10—C11—H11	121.2
C8—N2—C9	109.8 (4)	C11—C10—C9	121.7 (5)
C7—N1—C8	121.7 (4)	C11—C10—S2	127.9 (4)
O1—C2—C3	118.9 (4)	C9—C10—S2	110.4 (4)
O1—C2—C1	121.9 (5)	C12—C13—C14	121.7 (6)
C3—C2—C1	119.2 (5)	C12—C13—H13	119.1
N2—C8—N1	121.2 (5)	C14—C13—H13	119.1
N2—C8—S2	116.7 (4)	C13—C14—C9	118.4 (6)
N1—C8—S2	122.1 (4)	C13—C14—H14	120.8
C6—C5—C4	119.7 (5)	C9—C14—H14	120.8
C2—C1—C6—C5	0.8 (7)	C8—N2—C9—C10	0.7 (6)
C7—C1—C6—C5	−179.3 (4)	C8—N2—C9—C14	−180.0 (5)
C6—C1—C2—O1	−179.1 (5)	O1—C2—C3—C4	178.9 (5)
C7—C1—C2—O1	1.1 (7)	C1—C2—C3—C4	0.0 (7)
C6—C1—C2—C3	−0.1 (7)	C5—C4—C3—C2	−0.4 (8)
C7—C1—C2—C3	−180.0 (5)	C13—C12—C11—C10	1.2 (9)
C9—N2—C8—N1	178.7 (4)	C12—C11—C10—C9	−1.6 (8)
C9—N2—C8—S2	−0.6 (6)	C12—C11—C10—S2	−179.6 (4)
C7—N1—C8—N2	−177.8 (5)	N2—C9—C10—C11	−178.8 (5)
C7—N1—C8—S2	1.5 (7)	C14—C9—C10—C11	1.8 (8)
C10—S2—C8—N2	0.3 (4)	N2—C9—C10—S2	−0.4 (6)
C10—S2—C8—N1	−179.0 (4)	C14—C9—C10—S2	−179.8 (4)
C1—C6—C5—C4	−1.3 (7)	C8—S2—C10—C11	178.3 (5)
C1—C6—C5—Br1	179.5 (4)	C8—S2—C10—C9	0.1 (4)
C3—C4—C5—C6	1.1 (7)	C11—C12—C13—C14	−1.0 (9)
C3—C4—C5—Br1	−179.7 (4)	C12—C13—C14—C9	1.2 (9)
C8—N1—C7—C1	178.3 (4)	C10—C9—C14—C13	−1.5 (8)
C6—C1—C7—N1	179.0 (4)	N2—C9—C14—C13	179.1 (5)
C2—C1—C7—N1	−1.1 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.600 (6)	148
C7—H7···O1i	0.93	2.47	3.345 (6)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.87	2.600 (6)	148
C7—H7⋯O1i	0.93	2.47	3.345 (6)	157

Symmetry code: (i) .