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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2009 Mar 14;65(Pt 4):o759. doi: 10.1107/S1600536809008514

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

Khadija O Badahdaha a, Abdullah Mohamed Asiri a, Seik Weng Ng b,*
PMCID: PMC2968843  PMID: 21582489

Abstract

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.

Related literature

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 ▶).graphic file with name e-65-0o759-scheme1.jpg

Experimental

Crystal data

  • C18H12N2OS

  • M r = 304.36

  • Monoclinic, Inline graphic

  • a = 9.6398 (2) Å

  • b = 14.9687 (4) Å

  • c = 9.6646 (2) Å

  • β = 101.323 (2)°

  • V = 1367.41 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 123 K

  • 0.25 × 0.20 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.943, T max = 0.988

  • 12442 measured reflections

  • 3139 independent reflections

  • 2396 reflections with I > 2σ(I)

  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043

  • wR(F 2) = 0.122

  • S = 1.02

  • 3139 reflections

  • 203 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.53 e Å−3

  • Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008514/lh2783sup1.cif

e-65-0o759-sup1.cif (17.8KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008514/lh2783Isup2.hkl

e-65-0o759-Isup2.hkl (154KB, hkl)

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯N1 0.84 (1) 1.82 (2) 2.573 (2) 148 (3)
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Acknowledgments

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

supplementary crystallographic information

Comment

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

Experimental

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

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.

Figures

Fig. 1.

Fig. 1.

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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.

Crystal data

C18H12N2OS F(000) = 632
Mr = 304.36 Dx = 1.481 Mg m−3
Monoclinic, P21/n Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn Cell parameters from 2677 reflections
a = 9.6398 (2) Å θ = 2.5–28.1°
b = 14.9687 (4) Å µ = 0.24 mm−1
c = 9.6646 (2) Å T = 123 K
β = 101.323 (2)° Irregular block, orange
V = 1367.41 (5) Å3 0.25 × 0.20 × 0.05 mm
Z = 4
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Data collection

Bruker SMART APEX diffractometer 3139 independent reflections
Radiation source: fine-focus sealed tube 2396 reflections with I > 2˘I)
graphite Rint = 0.051
ω scans θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −12→12
Tmin = 0.943, Tmax = 0.988 k = −19→19
12442 measured reflections l = −12→12
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Refinement

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)] = 0.043 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122 H 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 parameters Δρmax = 0.53 e Å−3
1 restraint Δρmin = −0.23 e Å−3
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Special details

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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
S1 0.62414 (5) 0.57067 (3) 0.89471 (5) 0.02326 (15)
O1 0.28598 (15) 0.35583 (9) 0.77536 (15) 0.0261 (3)
H1 0.348 (2) 0.3964 (14) 0.782 (3) 0.057 (9)*
N1 0.41330 (16) 0.49518 (10) 0.70645 (17) 0.0214 (4)
N2 0.53279 (16) 0.62326 (11) 0.63631 (17) 0.0218 (3)
C1 0.19789 (19) 0.36352 (12) 0.6498 (2) 0.0207 (4)
C2 0.0903 (2) 0.29840 (13) 0.6173 (2) 0.0236 (4)
H2 0.0831 0.2524 0.6833 0.028*
C3 −0.0028 (2) 0.30118 (13) 0.4924 (2) 0.0227 (4)
H3 −0.0733 0.2562 0.4715 0.027*
C4 0.00270 (19) 0.37013 (12) 0.3918 (2) 0.0205 (4)
C5 −0.0966 (2) 0.37268 (13) 0.2635 (2) 0.0242 (4)
H5 −0.1667 0.3274 0.2434 0.029*
C6 −0.0935 (2) 0.43936 (14) 0.1678 (2) 0.0257 (4)
H6 −0.1613 0.4407 0.0819 0.031*
C7 0.0109 (2) 0.50600 (13) 0.1975 (2) 0.0246 (4)
H7 0.0131 0.5526 0.1312 0.030*
C8 0.1093 (2) 0.50481 (13) 0.3206 (2) 0.0219 (4)
H8 0.1790 0.5504 0.3380 0.026*
C9 0.10912 (19) 0.43680 (12) 0.42252 (19) 0.0189 (4)
C10 0.20982 (19) 0.43225 (12) 0.5546 (2) 0.0190 (4)
C11 0.3197 (2) 0.49736 (13) 0.5896 (2) 0.0210 (4)
H11 0.3245 0.5443 0.5245 0.025*
C12 0.51359 (19) 0.56351 (12) 0.7280 (2) 0.0205 (4)
C13 0.64047 (19) 0.68133 (12) 0.6951 (2) 0.0199 (4)
C14 0.6849 (2) 0.75430 (13) 0.6250 (2) 0.0230 (4)
H14 0.6414 0.7675 0.5303 0.028*
C15 0.7934 (2) 0.80674 (13) 0.6964 (2) 0.0251 (4)
H15 0.8252 0.8562 0.6495 0.030*
C16 0.8576 (2) 0.78866 (13) 0.8360 (2) 0.0256 (4)
H16 0.9320 0.8260 0.8826 0.031*
C17 0.8139 (2) 0.71684 (13) 0.9077 (2) 0.0245 (4)
H17 0.8570 0.7046 1.0029 0.029*
C18 0.7052 (2) 0.66319 (13) 0.8359 (2) 0.0214 (4)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
S1 0.0230 (3) 0.0244 (3) 0.0214 (3) −0.00141 (19) 0.00199 (18) 0.00103 (19)
O1 0.0272 (7) 0.0245 (8) 0.0252 (7) −0.0027 (6) 0.0017 (6) 0.0047 (6)
N1 0.0198 (8) 0.0208 (8) 0.0237 (8) −0.0009 (6) 0.0049 (6) −0.0016 (7)
N2 0.0210 (8) 0.0221 (8) 0.0220 (8) −0.0008 (6) 0.0034 (6) −0.0001 (7)
C1 0.0204 (9) 0.0202 (9) 0.0224 (10) 0.0019 (7) 0.0065 (7) −0.0006 (7)
C2 0.0261 (10) 0.0194 (9) 0.0276 (10) −0.0001 (8) 0.0112 (8) 0.0027 (8)
C3 0.0211 (9) 0.0188 (9) 0.0301 (11) −0.0030 (7) 0.0098 (8) −0.0036 (8)
C4 0.0197 (9) 0.0193 (9) 0.0241 (10) 0.0010 (7) 0.0081 (7) −0.0031 (8)
C5 0.0198 (9) 0.0231 (10) 0.0295 (11) −0.0015 (8) 0.0045 (8) −0.0066 (8)
C6 0.0240 (10) 0.0278 (11) 0.0235 (10) 0.0055 (8) 0.0006 (8) −0.0047 (8)
C7 0.0280 (10) 0.0238 (10) 0.0230 (10) 0.0048 (8) 0.0074 (8) 0.0007 (8)
C8 0.0227 (9) 0.0194 (9) 0.0249 (10) −0.0009 (7) 0.0078 (8) −0.0013 (8)
C9 0.0185 (9) 0.0178 (9) 0.0216 (9) 0.0025 (7) 0.0067 (7) −0.0019 (7)
C10 0.0183 (9) 0.0176 (9) 0.0223 (9) 0.0018 (7) 0.0072 (7) −0.0015 (7)
C11 0.0218 (9) 0.0192 (9) 0.0236 (10) 0.0007 (7) 0.0082 (7) 0.0005 (8)
C12 0.0191 (9) 0.0213 (9) 0.0210 (9) 0.0024 (7) 0.0035 (7) −0.0024 (7)
C13 0.0181 (9) 0.0186 (9) 0.0236 (10) 0.0031 (7) 0.0053 (7) −0.0030 (7)
C14 0.0229 (9) 0.0213 (10) 0.0247 (10) 0.0020 (8) 0.0050 (8) −0.0003 (8)
C15 0.0256 (10) 0.0201 (10) 0.0311 (11) 0.0003 (8) 0.0093 (8) −0.0006 (8)
C16 0.0214 (9) 0.0235 (10) 0.0319 (11) −0.0011 (8) 0.0057 (8) −0.0065 (8)
C17 0.0223 (10) 0.0280 (11) 0.0229 (10) 0.0028 (8) 0.0037 (8) −0.0041 (8)
C18 0.0204 (9) 0.0220 (9) 0.0227 (10) 0.0028 (8) 0.0067 (7) −0.0026 (8)
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Geometric parameters (Å, °)

S1—C18 1.740 (2) C6—H6 0.9500
S1—C12 1.7519 (19) C7—C8 1.368 (3)
O1—C1 1.343 (2) C7—H7 0.9500
O1—H1 0.843 (10) C8—C9 1.417 (3)
N1—C11 1.300 (2) C8—H8 0.9500
N1—C12 1.395 (2) C9—C10 1.445 (3)
N2—C12 1.298 (2) C10—C11 1.430 (3)
N2—C13 1.387 (2) C11—H11 0.9500
C1—C10 1.400 (3) C13—C14 1.396 (3)
C1—C2 1.413 (3) C13—C18 1.408 (3)
C2—C3 1.356 (3) C14—C15 1.380 (3)
C2—H2 0.9500 C14—H14 0.9500
C3—C4 1.426 (3) C15—C16 1.397 (3)
C3—H3 0.9500 C15—H15 0.9500
C4—C5 1.410 (3) C16—C17 1.388 (3)
C4—C9 1.420 (3) C16—H16 0.9500
C5—C6 1.365 (3) C17—C18 1.392 (3)
C5—H5 0.9500 C17—H17 0.9500
C6—C7 1.406 (3)
C18—S1—C12 88.83 (9) C8—C9—C10 123.76 (17)
C1—O1—H1 109 (2) C4—C9—C10 118.92 (17)
C11—N1—C12 116.99 (16) C1—C10—C11 119.86 (17)
C12—N2—C13 110.36 (16) C1—C10—C9 119.17 (17)
O1—C1—C10 122.56 (17) C11—C10—C9 120.96 (17)
O1—C1—C2 116.63 (17) N1—C11—C10 122.94 (18)
C10—C1—C2 120.82 (18) N1—C11—H11 118.5
C3—C2—C1 120.34 (18) C10—C11—H11 118.5
C3—C2—H2 119.8 N2—C12—N1 126.25 (17)
C1—C2—H2 119.8 N2—C12—S1 116.32 (14)
C2—C3—C4 121.51 (18) N1—C12—S1 117.44 (14)
C2—C3—H3 119.2 N2—C13—C14 124.58 (17)
C4—C3—H3 119.2 N2—C13—C18 115.42 (17)
C5—C4—C9 120.17 (18) C14—C13—C18 120.00 (17)
C5—C4—C3 120.62 (17) C15—C14—C13 118.50 (18)
C9—C4—C3 119.21 (18) C15—C14—H14 120.8
C6—C5—C4 120.93 (18) C13—C14—H14 120.7
C6—C5—H5 119.5 C14—C15—C16 121.43 (19)
C4—C5—H5 119.5 C14—C15—H15 119.3
C5—C6—C7 119.37 (19) C16—C15—H15 119.3
C5—C6—H6 120.3 C17—C16—C15 120.81 (19)
C7—C6—H6 120.3 C17—C16—H16 119.6
C8—C7—C6 120.97 (19) C15—C16—H16 119.6
C8—C7—H7 119.5 C16—C17—C18 118.07 (19)
C6—C7—H7 119.5 C16—C17—H17 121.0
C7—C8—C9 121.24 (18) C18—C17—H17 121.0
C7—C8—H8 119.4 C17—C18—C13 121.18 (18)
C9—C8—H8 119.4 C17—C18—S1 129.72 (16)
C8—C9—C4 117.32 (17) C13—C18—S1 109.07 (14)
O1—C1—C2—C3 −179.77 (17) C12—N1—C11—C10 −179.24 (16)
C10—C1—C2—C3 0.5 (3) C1—C10—C11—N1 1.6 (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—N1 179.17 (17)
C2—C3—C4—C9 0.7 (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—C6 178.85 (18) C11—N1—C12—S1 171.09 (14)
C4—C5—C6—C7 0.4 (3) C18—S1—C12—N2 −0.17 (15)
C5—C6—C7—C8 0.2 (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—C18 0.8 (2)
C7—C8—C9—C10 −179.70 (17) N2—C13—C14—C15 179.92 (17)
C5—C4—C9—C8 0.6 (3) C18—C13—C14—C15 0.6 (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—C17 0.1 (3)
C3—C4—C9—C10 0.6 (3) C15—C16—C17—C18 0.4 (3)
O1—C1—C10—C11 0.4 (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—C9 0.9 (3) C14—C13—C18—C17 −0.1 (3)
C8—C9—C10—C1 178.24 (17) N2—C13—C18—S1 −0.9 (2)
C4—C9—C10—C1 −1.4 (3) C14—C13—C18—S1 178.42 (14)
C8—C9—C10—C11 −1.0 (3) C12—S1—C18—C17 178.94 (19)
C4—C9—C10—C11 179.39 (17) C12—S1—C18—C13 0.60 (14)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O1—H1···N1 0.84 (1) 1.82 (2) 2.573 (2) 148 (3)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2783).

References

  1. Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  2. Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Büyükgüngör, O., Çalışkan, N., Davran, C. & Batı, H. (2004). Acta Cryst. E60, o1414–o1416.
  4. Cannon, D., Quesada, A., Quiroga, J., Insuasty, B., Abonia, R., Hernández, P., Cobo, J., Nogueras, M., Sánchez, A. & Low, J. N. (2001). Acta Cryst. E57, o180–o181.
  5. Guo, Y.-S., Yu, Z.-H. & Jin, X.-L. (2002). Acta Chim. Sin.60, 228–233.
  6. Saraçoğlu, H., Çalışkan, N., Davran, C., Soylu, S., Batı, H. & Büyükgüngör, O. (2004). Acta Cryst. E60, o2090–o2092. [DOI] [PubMed]
  7. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  8. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  9. Westrip, S. P. (2009). publCIF In preparation.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008514/lh2783sup1.cif

e-65-0o759-sup1.cif (17.8KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008514/lh2783Isup2.hkl

e-65-0o759-Isup2.hkl (154KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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