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

The title compound, C(14)H(10)N(2)OS, is nearly planar, with a maximum deviation of 0.0698 (13) Å from the mean plane, and exists in an E configuration with respect to the C=N bond. The dihedral angle between the two benzene rings is 2.81 (9)°. There is an intra-molecular O-H⋯N hydrogen bond and inter-molecular C-H⋯O and C-H⋯N hydrogen bonds.

Related literature

For related structures of 2-amino­benzothia­zole derivatives and their Schiff bases, see: Büyükgüngör et al. (2004 ▶); Liang et al. (1999 ▶); Liu et al. (2009 ▶). For the biological activity of the title compound and related structures, see: Yan et al. (1999 ▶).

Experimental

Crystal data

C14H10N2OS

M = 254.30

Orthorhombic,

a = 12.150 (2) Å

b = 8.9578 (15) Å

c = 22.026 (4) Å

V = 2397.4 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 298 K

0.51 × 0.15 × 0.11 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

12166 measured reflections

2353 independent reflections

1939 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.113

S = 1.06

2353 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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/S1600536809007934/is2387sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007934/is2387Isup2.hkl

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

C14H10N2OS	Dx = 1.409 Mg m−3
Mr = 254.30	Melting point: 417 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3147 reflections
a = 12.150 (2) Å	θ = 2.5–27.1°
b = 8.9578 (15) Å	µ = 0.26 mm−1
c = 22.026 (4) Å	T = 298 K
V = 2397.4 (7) Å3	Rod, yellow
Z = 8	0.51 × 0.15 × 0.11 mm
F(000) = 1056

Bruker SMART APEX diffractometer	1939 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
graphite	θmax = 26.0°, θmin = 1.9°
φ and ω scans	h = −14→14
12166 measured reflections	k = −11→10
2353 independent reflections	l = −27→18

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) = 0.113	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.4758P] where P = (Fo2 + 2Fc2)/3
2353 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.24 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
C1	0.88027 (14)	0.3483 (2)	0.21383 (9)	0.0409 (4)
C2	0.91856 (18)	0.4419 (2)	0.16848 (10)	0.0541 (6)
H2	0.9937	0.4497	0.1611	0.065*
C3	0.8451 (2)	0.5230 (3)	0.13448 (10)	0.0570 (6)
H3	0.8715	0.5858	0.1042	0.068*
C4	0.73328 (19)	0.5138 (2)	0.14422 (9)	0.0530 (5)
H4	0.6847	0.5691	0.1206	0.064*
C5	0.69463 (16)	0.4221 (2)	0.18923 (9)	0.0451 (5)
H5	0.6192	0.4159	0.1960	0.054*
C6	0.76636 (14)	0.3374 (2)	0.22515 (8)	0.0370 (4)
C7	0.72317 (13)	0.2428 (2)	0.27182 (8)	0.0381 (4)
H7	0.6474	0.2382	0.2773	0.046*
C8	0.74236 (14)	0.0726 (2)	0.35054 (8)	0.0366 (4)
C9	0.74360 (15)	−0.0870 (2)	0.42653 (8)	0.0397 (4)
C10	0.78616 (17)	−0.1805 (2)	0.47105 (9)	0.0519 (5)
H10	0.8619	−0.1912	0.4753	0.062*
C11	0.71662 (19)	−0.2563 (3)	0.50844 (10)	0.0574 (6)
H11	0.7452	−0.3190	0.5382	0.069*
C12	0.60333 (19)	−0.2410 (3)	0.50247 (11)	0.0614 (6)
H12	0.5570	−0.2935	0.5284	0.074*
C13	0.55866 (18)	−0.1495 (3)	0.45897 (10)	0.0589 (6)
H13	0.4828	−0.1395	0.4551	0.071*
C14	0.62954 (15)	−0.0724 (2)	0.42097 (9)	0.0419 (4)
N1	0.80522 (12)	−0.00477 (18)	0.38564 (7)	0.0419 (4)
N2	0.78539 (11)	0.16428 (17)	0.30618 (7)	0.0382 (4)
O1	0.95340 (10)	0.26804 (18)	0.24619 (7)	0.0549 (4)
H1	0.9210	0.2214	0.2728	0.082*
S1	0.59914 (4)	0.05133 (6)	0.36285 (2)	0.04566 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0337 (9)	0.0443 (11)	0.0447 (10)	−0.0016 (8)	0.0039 (8)	−0.0077 (8)
C2	0.0457 (11)	0.0596 (14)	0.0571 (13)	−0.0105 (10)	0.0130 (10)	−0.0046 (10)
C3	0.0714 (16)	0.0517 (13)	0.0480 (12)	−0.0107 (12)	0.0098 (11)	0.0030 (10)
C4	0.0639 (14)	0.0503 (12)	0.0449 (12)	0.0039 (11)	−0.0043 (10)	0.0009 (9)
C5	0.0394 (10)	0.0477 (12)	0.0481 (11)	0.0018 (9)	−0.0018 (8)	−0.0045 (9)
C6	0.0320 (9)	0.0384 (10)	0.0405 (10)	−0.0008 (7)	0.0018 (7)	−0.0081 (8)
C7	0.0261 (8)	0.0428 (10)	0.0455 (10)	−0.0003 (8)	0.0018 (7)	−0.0058 (8)
C8	0.0277 (9)	0.0405 (10)	0.0416 (10)	0.0008 (7)	0.0012 (7)	−0.0073 (8)
C9	0.0390 (10)	0.0424 (11)	0.0378 (10)	0.0018 (8)	0.0022 (8)	−0.0064 (8)
C10	0.0478 (11)	0.0582 (13)	0.0497 (12)	0.0082 (10)	−0.0029 (9)	0.0003 (10)
C11	0.0681 (14)	0.0566 (14)	0.0475 (12)	0.0035 (11)	−0.0003 (10)	0.0086 (10)
C12	0.0591 (14)	0.0670 (15)	0.0579 (14)	−0.0063 (12)	0.0101 (10)	0.0144 (12)
C13	0.0427 (11)	0.0685 (15)	0.0656 (14)	−0.0061 (10)	0.0086 (10)	0.0116 (12)
C14	0.0384 (9)	0.0430 (11)	0.0443 (11)	−0.0005 (8)	0.0002 (8)	−0.0022 (8)
N1	0.0332 (8)	0.0472 (9)	0.0453 (9)	0.0050 (7)	0.0017 (7)	−0.0014 (8)
N2	0.0302 (7)	0.0420 (9)	0.0425 (8)	0.0007 (6)	0.0034 (6)	−0.0034 (7)
O1	0.0289 (6)	0.0699 (10)	0.0660 (10)	0.0016 (7)	0.0052 (6)	0.0088 (8)
S1	0.0277 (3)	0.0558 (4)	0.0535 (3)	−0.0020 (2)	−0.00019 (19)	0.0079 (2)

C1—O1	1.347 (2)	C8—N2	1.379 (2)
C1—C2	1.384 (3)	C8—S1	1.7714 (18)
C1—C6	1.410 (2)	C9—N1	1.384 (2)
C2—C3	1.373 (3)	C9—C10	1.389 (3)
C2—H2	0.9300	C9—C14	1.397 (3)
C3—C4	1.378 (3)	C10—C11	1.362 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.371 (3)	C11—C12	1.390 (3)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.400 (3)	C12—C13	1.373 (3)
C5—H5	0.9300	C12—H12	0.9300
C6—C7	1.432 (3)	C13—C14	1.385 (3)
C7—N2	1.280 (2)	C13—H13	0.9300
C7—H7	0.9300	C14—S1	1.733 (2)
C8—N1	1.289 (2)	O1—H1	0.8200
O1—C1—C2	118.89 (16)	N2—C8—S1	123.03 (13)
O1—C1—C6	121.15 (17)	N1—C9—C10	125.37 (17)
C2—C1—C6	119.96 (18)	N1—C9—C14	115.45 (16)
C3—C2—C1	119.71 (19)	C10—C9—C14	119.17 (18)
C3—C2—H2	120.1	C11—C10—C9	119.79 (19)
C1—C2—H2	120.1	C11—C10—H10	120.1
C2—C3—C4	121.6 (2)	C9—C10—H10	120.1
C2—C3—H3	119.2	C10—C11—C12	120.5 (2)
C4—C3—H3	119.2	C10—C11—H11	119.7
C5—C4—C3	119.1 (2)	C12—C11—H11	119.7
C5—C4—H4	120.4	C13—C12—C11	121.1 (2)
C3—C4—H4	120.4	C13—C12—H12	119.4
C4—C5—C6	121.34 (19)	C11—C12—H12	119.4
C4—C5—H5	119.3	C12—C13—C14	118.3 (2)
C6—C5—H5	119.3	C12—C13—H13	120.9
C5—C6—C1	118.29 (17)	C14—C13—H13	120.9
C5—C6—C7	119.87 (16)	C13—C14—C9	121.12 (18)
C1—C6—C7	121.84 (17)	C13—C14—S1	129.24 (16)
N2—C7—C6	122.23 (15)	C9—C14—S1	109.64 (14)
N2—C7—H7	118.9	C8—N1—C9	110.86 (15)
C6—C7—H7	118.9	C7—N2—C8	121.47 (15)
N1—C8—N2	121.36 (16)	C1—O1—H1	109.5
N1—C8—S1	115.61 (14)	C14—S1—C8	88.44 (9)
O1—C1—C2—C3	179.13 (19)	C12—C13—C14—C9	0.1 (3)
C6—C1—C2—C3	−0.4 (3)	C12—C13—C14—S1	−179.36 (17)
C1—C2—C3—C4	−0.1 (3)	N1—C9—C14—C13	179.63 (19)
C2—C3—C4—C5	0.5 (3)	C10—C9—C14—C13	−0.1 (3)
C3—C4—C5—C6	−0.3 (3)	N1—C9—C14—S1	−0.8 (2)
C4—C5—C6—C1	−0.2 (3)	C10—C9—C14—S1	179.44 (15)
C4—C5—C6—C7	179.96 (18)	N2—C8—N1—C9	179.65 (15)
O1—C1—C6—C5	−178.96 (17)	S1—C8—N1—C9	−1.0 (2)
C2—C1—C6—C5	0.5 (3)	C10—C9—N1—C8	−179.13 (18)
O1—C1—C6—C7	0.9 (3)	C14—C9—N1—C8	1.2 (2)
C2—C1—C6—C7	−179.64 (18)	C6—C7—N2—C8	−179.39 (16)
C5—C6—C7—N2	−179.38 (17)	N1—C8—N2—C7	−179.05 (17)
C1—C6—C7—N2	0.8 (3)	S1—C8—N2—C7	1.6 (2)
N1—C9—C10—C11	−179.61 (19)	C13—C14—S1—C8	179.7 (2)
C14—C9—C10—C11	0.1 (3)	C9—C14—S1—C8	0.24 (14)
C9—C10—C11—C12	−0.1 (3)	N1—C8—S1—C14	0.43 (15)
C10—C11—C12—C13	0.0 (4)	N2—C8—S1—C14	179.80 (15)
C11—C12—C13—C14	0.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.82	1.88	2.6034 (19)	147
C7—H7···O1i	0.93	2.43	3.309 (2)	158
C2—H2···N1ii	0.93	2.68	3.593 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.82	1.88	2.6034 (19)	147
C7—H7⋯O1i	0.93	2.43	3.309 (2)	158
C2—H2⋯N1ii	0.93	2.68	3.593 (2)	167

Symmetry codes: (i) ; (ii) .