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Acta Cryst. (2009). E65, o759    [ doi:10.1107/S1600536809008514 ]

2-(1,3-Benzothiazol-2-yliminomethyl)-2-naphthol

K. O. Badahdaha, A. M. Asiri and S. W. Ng

Abstract top

In the title molecule, C18H12N2OS, the dihedral angle between the two fused-ring systems is 7.2 (1)°. The hydroxy group forms an intramolecular hydrogen bond with the imino group.

Comment top

The molecular structure of the title compound is shown in Fig. 1.

Related literature top

For the crystal structures of other Schiff bases derived by condensing benzthiazolyl-2-amine with aldehydes/ketones, see: Büyükgüngör et al. (2004); Cannon et al. (2001); Guo et al. (2002); Saraçoğlu et al. (2004).

Experimental top

2-Aminobenzothiazole (4.0 g, 26.6 mmol) dissolved in ethanol (25 ml) was added to 2-hydroxybenzaldehyde (4.58 g, 26.6 mmol) dissolved in ethanol (25 ml). The mixture was heated for another hour. The solid that separated from the reaction mixture was isolated and recrystallized from ethanol.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) fixed at 1.2U(C).

The hydroxy H-atom was located in a difference Fouier map, and was refined with a distance restraint of O–H 0.84±0.01 Å; its isotropic displacement parameter was refined.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellisoid plot (Barbour, 2001) of C18H12N2OS; probability levels are set at 70% and H-atoms are drawn as spheres of arbitrary radius. The dashed line denotes the hydrogen bond.
2-(1,3-Benzothiazol-2-yliminomethyl)-2-naphthol top
Crystal data top
C18H12N2OSF(000) = 632
Mr = 304.36Dx = 1.481 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2677 reflections
a = 9.6398 (2) Åθ = 2.5–28.1°
b = 14.9687 (4) ŵ = 0.24 mm−1
c = 9.6646 (2) ÅT = 123 K
β = 101.323 (2)°Irregular block, orange
V = 1367.41 (5) Å30.25 × 0.20 × 0.05 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer		3139 independent reflections
Radiation source: fine-focus sealed tube2396 reflections with I > 2˘I)
graphiteRint = 0.051
ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→12
Tmin = 0.943, Tmax = 0.988k = −19→19
12442 measured reflectionsl = −12→12
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0612P)2 + 0.543P]
where P = (Fo2 + 2Fc2)/3
3139 reflections(Δ/σ)max = 0.001
203 parametersΔρmax = 0.53 e Å−3
1 restraintΔρmin = −0.23 e Å−3
Crystal data top
C18H12N2OSV = 1367.41 (5) Å3
Mr = 304.36Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.6398 (2) ŵ = 0.24 mm−1
b = 14.9687 (4) ÅT = 123 K
c = 9.6646 (2) Å0.25 × 0.20 × 0.05 mm
β = 101.323 (2)°
Data collection top
Bruker SMART APEX
diffractometer		3139 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2396 reflections with I > 2˘I)
Tmin = 0.943, Tmax = 0.988Rint = 0.051
12442 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.122Δρmax = 0.53 e Å−3
S = 1.02Δρmin = −0.23 e Å−3
3139 reflectionsAbsolute structure: ?
203 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.62414 (5)0.57067 (3)0.89471 (5)0.02326 (15)
O10.28598 (15)0.35583 (9)0.77536 (15)0.0261 (3)
H10.348 (2)0.3964 (14)0.782 (3)0.057 (9)*
N10.41330 (16)0.49518 (10)0.70645 (17)0.0214 (4)
N20.53279 (16)0.62326 (11)0.63631 (17)0.0218 (3)
C10.19789 (19)0.36352 (12)0.6498 (2)0.0207 (4)
C20.0903 (2)0.29840 (13)0.6173 (2)0.0236 (4)
H20.08310.25240.68330.028*
C3−0.0028 (2)0.30118 (13)0.4924 (2)0.0227 (4)
H3−0.07330.25620.47150.027*
C40.00270 (19)0.37013 (12)0.3918 (2)0.0205 (4)
C5−0.0966 (2)0.37268 (13)0.2635 (2)0.0242 (4)
H5−0.16670.32740.24340.029*
C6−0.0935 (2)0.43936 (14)0.1678 (2)0.0257 (4)
H6−0.16130.44070.08190.031*
C70.0109 (2)0.50600 (13)0.1975 (2)0.0246 (4)
H70.01310.55260.13120.030*
C80.1093 (2)0.50481 (13)0.3206 (2)0.0219 (4)
H80.17900.55040.33800.026*
C90.10912 (19)0.43680 (12)0.42252 (19)0.0189 (4)
C100.20982 (19)0.43225 (12)0.5546 (2)0.0190 (4)
C110.3197 (2)0.49736 (13)0.5896 (2)0.0210 (4)
H110.32450.54430.52450.025*
C120.51359 (19)0.56351 (12)0.7280 (2)0.0205 (4)
C130.64047 (19)0.68133 (12)0.6951 (2)0.0199 (4)
C140.6849 (2)0.75430 (13)0.6250 (2)0.0230 (4)
H140.64140.76750.53030.028*
C150.7934 (2)0.80674 (13)0.6964 (2)0.0251 (4)
H150.82520.85620.64950.030*
C160.8576 (2)0.78866 (13)0.8360 (2)0.0256 (4)
H160.93200.82600.88260.031*
C170.8139 (2)0.71684 (13)0.9077 (2)0.0245 (4)
H170.85700.70461.00290.029*
C180.7052 (2)0.66319 (13)0.8359 (2)0.0214 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0230 (3)0.0244 (3)0.0214 (3)−0.00141 (19)0.00199 (18)0.00103 (19)
O10.0272 (7)0.0245 (8)0.0252 (7)−0.0027 (6)0.0017 (6)0.0047 (6)
N10.0198 (8)0.0208 (8)0.0237 (8)−0.0009 (6)0.0049 (6)−0.0016 (7)
N20.0210 (8)0.0221 (8)0.0220 (8)−0.0008 (6)0.0034 (6)−0.0001 (7)
C10.0204 (9)0.0202 (9)0.0224 (10)0.0019 (7)0.0065 (7)−0.0006 (7)
C20.0261 (10)0.0194 (9)0.0276 (10)−0.0001 (8)0.0112 (8)0.0027 (8)
C30.0211 (9)0.0188 (9)0.0301 (11)−0.0030 (7)0.0098 (8)−0.0036 (8)
C40.0197 (9)0.0193 (9)0.0241 (10)0.0010 (7)0.0081 (7)−0.0031 (8)
C50.0198 (9)0.0231 (10)0.0295 (11)−0.0015 (8)0.0045 (8)−0.0066 (8)
C60.0240 (10)0.0278 (11)0.0235 (10)0.0055 (8)0.0006 (8)−0.0047 (8)
C70.0280 (10)0.0238 (10)0.0230 (10)0.0048 (8)0.0074 (8)0.0007 (8)
C80.0227 (9)0.0194 (9)0.0249 (10)−0.0009 (7)0.0078 (8)−0.0013 (8)
C90.0185 (9)0.0178 (9)0.0216 (9)0.0025 (7)0.0067 (7)−0.0019 (7)
C100.0183 (9)0.0176 (9)0.0223 (9)0.0018 (7)0.0072 (7)−0.0015 (7)
C110.0218 (9)0.0192 (9)0.0236 (10)0.0007 (7)0.0082 (7)0.0005 (8)
C120.0191 (9)0.0213 (9)0.0210 (9)0.0024 (7)0.0035 (7)−0.0024 (7)
C130.0181 (9)0.0186 (9)0.0236 (10)0.0031 (7)0.0053 (7)−0.0030 (7)
C140.0229 (9)0.0213 (10)0.0247 (10)0.0020 (8)0.0050 (8)−0.0003 (8)
C150.0256 (10)0.0201 (10)0.0311 (11)0.0003 (8)0.0093 (8)−0.0006 (8)
C160.0214 (9)0.0235 (10)0.0319 (11)−0.0011 (8)0.0057 (8)−0.0065 (8)
C170.0223 (10)0.0280 (11)0.0229 (10)0.0028 (8)0.0037 (8)−0.0041 (8)
C180.0204 (9)0.0220 (9)0.0227 (10)0.0028 (8)0.0067 (7)−0.0026 (8)
Geometric parameters (Å, °) top
S1—C181.740 (2)C6—H60.9500
S1—C121.7519 (19)C7—C81.368 (3)
O1—C11.343 (2)C7—H70.9500
O1—H10.843 (10)C8—C91.417 (3)
N1—C111.300 (2)C8—H80.9500
N1—C121.395 (2)C9—C101.445 (3)
N2—C121.298 (2)C10—C111.430 (3)
N2—C131.387 (2)C11—H110.9500
C1—C101.400 (3)C13—C141.396 (3)
C1—C21.413 (3)C13—C181.408 (3)
C2—C31.356 (3)C14—C151.380 (3)
C2—H20.9500C14—H140.9500
C3—C41.426 (3)C15—C161.397 (3)
C3—H30.9500C15—H150.9500
C4—C51.410 (3)C16—C171.388 (3)
C4—C91.420 (3)C16—H160.9500
C5—C61.365 (3)C17—C181.392 (3)
C5—H50.9500C17—H170.9500
C6—C71.406 (3)
C18—S1—C1288.83 (9)C8—C9—C10123.76 (17)
C1—O1—H1109 (2)C4—C9—C10118.92 (17)
C11—N1—C12116.99 (16)C1—C10—C11119.86 (17)
C12—N2—C13110.36 (16)C1—C10—C9119.17 (17)
O1—C1—C10122.56 (17)C11—C10—C9120.96 (17)
O1—C1—C2116.63 (17)N1—C11—C10122.94 (18)
C10—C1—C2120.82 (18)N1—C11—H11118.5
C3—C2—C1120.34 (18)C10—C11—H11118.5
C3—C2—H2119.8N2—C12—N1126.25 (17)
C1—C2—H2119.8N2—C12—S1116.32 (14)
C2—C3—C4121.51 (18)N1—C12—S1117.44 (14)
C2—C3—H3119.2N2—C13—C14124.58 (17)
C4—C3—H3119.2N2—C13—C18115.42 (17)
C5—C4—C9120.17 (18)C14—C13—C18120.00 (17)
C5—C4—C3120.62 (17)C15—C14—C13118.50 (18)
C9—C4—C3119.21 (18)C15—C14—H14120.8
C6—C5—C4120.93 (18)C13—C14—H14120.7
C6—C5—H5119.5C14—C15—C16121.43 (19)
C4—C5—H5119.5C14—C15—H15119.3
C5—C6—C7119.37 (19)C16—C15—H15119.3
C5—C6—H6120.3C17—C16—C15120.81 (19)
C7—C6—H6120.3C17—C16—H16119.6
C8—C7—C6120.97 (19)C15—C16—H16119.6
C8—C7—H7119.5C16—C17—C18118.07 (19)
C6—C7—H7119.5C16—C17—H17121.0
C7—C8—C9121.24 (18)C18—C17—H17121.0
C7—C8—H8119.4C17—C18—C13121.18 (18)
C9—C8—H8119.4C17—C18—S1129.72 (16)
C8—C9—C4117.32 (17)C13—C18—S1109.07 (14)
O1—C1—C2—C3−179.77 (17)C12—N1—C11—C10−179.24 (16)
C10—C1—C2—C30.5 (3)C1—C10—C11—N11.6 (3)
C1—C2—C3—C4−1.3 (3)C9—C10—C11—N1−179.23 (17)
C2—C3—C4—C5−178.90 (18)C13—N2—C12—N1179.17 (17)
C2—C3—C4—C90.7 (3)C13—N2—C12—S1−0.3 (2)
C9—C4—C5—C6−0.8 (3)C11—N1—C12—N2−8.4 (3)
C3—C4—C5—C6178.85 (18)C11—N1—C12—S1171.09 (14)
C4—C5—C6—C70.4 (3)C18—S1—C12—N2−0.17 (15)
C5—C6—C7—C80.2 (3)C18—S1—C12—N1−179.72 (15)
C6—C7—C8—C9−0.3 (3)C12—N2—C13—C14−178.50 (17)
C7—C8—C9—C4−0.1 (3)C12—N2—C13—C180.8 (2)
C7—C8—C9—C10−179.70 (17)N2—C13—C14—C15179.92 (17)
C5—C4—C9—C80.6 (3)C18—C13—C14—C150.6 (3)
C3—C4—C9—C8−179.03 (16)C13—C14—C15—C16−0.6 (3)
C5—C4—C9—C10−179.76 (16)C14—C15—C16—C170.1 (3)
C3—C4—C9—C100.6 (3)C15—C16—C17—C180.4 (3)
O1—C1—C10—C110.4 (3)C16—C17—C18—C13−0.4 (3)
C2—C1—C10—C11−179.91 (17)C16—C17—C18—S1−178.59 (15)
O1—C1—C10—C9−178.88 (16)N2—C13—C18—C17−179.46 (17)
C2—C1—C10—C90.9 (3)C14—C13—C18—C17−0.1 (3)
C8—C9—C10—C1178.24 (17)N2—C13—C18—S1−0.9 (2)
C4—C9—C10—C1−1.4 (3)C14—C13—C18—S1178.42 (14)
C8—C9—C10—C11−1.0 (3)C12—S1—C18—C17178.94 (19)
C4—C9—C10—C11179.39 (17)C12—S1—C18—C130.60 (14)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.84 (1)1.82 (2)2.573 (2)148 (3)
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.84 (1)1.82 (2)2.573 (2)148 (3)
Acknowledgements top

We thank King Abdul Aziz University (grant No. 171/428) and the University of Malaya for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

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Büyükgüngör, O., Çalışkan, N., Davran, C. & Batı, H. (2004). Acta Cryst. E60, o1414–o1416

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Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.