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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1826.
Published online 2010 June 26. doi:  10.1107/S1600536810023755
PMCID: PMC3006974

A monoclinic modification of 2-[(1,3-benzothia­zol-2-yl)imino­meth­yl]phenol

Abstract

In the title Schiff base, C14H10N2OS, the azomethine double bond is in an E configuration; the benzothiazolyl ring (r.m.s. deviation = 0.007 Å) is coplanar with the phenyl­ene ring (r.m.s. deviation = 0.007 Å), the two rings being slightly bent at 2.6 (1)°. The hy­droxy H atom forms an intra­molecular hydrogen bond to the imino group. The bond dimensions of the monoclinic modification are similar to those of the ortho­rhom­bic modification [Liu et al. (2009 [triangle]). Acta Cryst. E65, o738].

Related literature

For an ortho­rhom­bic modification of this structure, see: Liu et al. (2009 [triangle]).

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Object name is e-66-o1826-scheme1.jpg

Experimental

Crystal data

  • C14H10N2OS
  • M r = 254.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1826-efi1.jpg
  • a = 8.6391 (4) Å
  • b = 6.2313 (4) Å
  • c = 11.4459 (8) Å
  • β = 108.893 (1)°
  • V = 582.97 (6) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.26 mm−1
  • T = 100 K
  • 0.14 × 0.13 × 0.08 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.964, T max = 0.979
  • 5307 measured reflections
  • 2599 independent reflections
  • 2512 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.110
  • S = 1.05
  • 2599 reflections
  • 164 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.40 e Å−3
  • Δρmin = −0.25 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1242 Friedel pairs
  • Flack parameter: 0.27 (8)

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023755/nk2043sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023755/nk2043Isup2.hkl

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

Acknowledgments

We thank King Abdul Aziz University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The orthorhombic modification of 2-[(1,3-benzothiazol-2-yl)iminomethyl]phenol (Scheme I) is a flat molecule having a (calculated) density of 1.409 g ml-1 (Liu et al., 2009). In the monoclinic modification, the packing is more compact (calculated density 1.449 g ml-1). The benzisotholyl ring [r.m.s. deviation 0.007 Å] is co-planar with the phenylene ring [r.m.s. deviation 0.007 Å], the two rings being slightly bent by 2.6 (1) ° only. The hydroxy H-atom forms an intramolecular hydrogen bond to the imino group (Fig. 1). The r.m.s. deviation of the non-hydrogen atoms for the least-squares plane is 0.034 Å, and all deviations deviate by 0.002 Å only.

Experimental

2-Aminobenzothiazole (0.50 g, 4.4 mol) and salicyladehyde (0.66 g, 4.4 mol) were heated in methanol (15 ml) for 5 h. Yellowish-orange crystals deposited when the solution was set aside for a day.

Refinement

Carbon-bound H-atoms were placed in calculated positions [C–H 0.95 Å, U(H) 1.2Ueq(C)] and were included in the refinement in the riding model approximation. The hydroxy H-atom was located in a difference Fourier map, but attempts to refine it even with a distance restraint led to a small temperature factor. The position and temperature factor were not refined. The structure is a racemic twin, the explicit refinement of the Flack parameter from 1242 Friedel pairs gave a value of 0.27 (8).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C14H10N2OS at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C14H10N2OSF(000) = 264
Mr = 254.30Dx = 1.449 Mg m3
Monoclinic, PnMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yacCell parameters from 3896 reflections
a = 8.6391 (4) Åθ = 2.6–28.3°
b = 6.2313 (4) ŵ = 0.26 mm1
c = 11.4459 (8) ÅT = 100 K
β = 108.893 (1)°Prism, orange
V = 582.97 (6) Å30.14 × 0.13 × 0.08 mm
Z = 2

Data collection

Bruker SMART APEX diffractometer2599 independent reflections
Radiation source: fine-focus sealed tube2512 reflections with I > 2σ(I)
graphiteRint = 0.029
ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→10
Tmin = 0.964, Tmax = 0.979k = −8→8
5307 measured reflectionsl = −14→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.110w = 1/[σ2(Fo2) + (0.0831P)2 + 0.0645P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2599 reflectionsΔρmax = 0.40 e Å3
164 parametersΔρmin = −0.25 e Å3
2 restraintsAbsolute structure: Flack (1983), 1242 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.27 (8)

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

xyzUiso*/Ueq
S10.50007 (6)0.06429 (7)0.49993 (5)0.01864 (15)
O10.7048 (2)0.5684 (3)0.89741 (16)0.0277 (4)
H10.69240.46230.84620.042*
N10.6095 (2)0.3254 (3)0.70823 (16)0.0186 (4)
N20.7613 (2)0.0261 (3)0.69409 (17)0.0193 (4)
C10.5700 (3)0.6867 (4)0.84466 (19)0.0195 (4)
C20.5445 (3)0.8696 (4)0.9059 (2)0.0222 (4)
H20.62270.90960.98250.027*
C30.4058 (3)0.9936 (4)0.8561 (2)0.0226 (5)
H30.38951.11830.89850.027*
C40.2898 (3)0.9363 (3)0.7441 (2)0.0228 (5)
H40.19371.02010.71080.027*
C50.3153 (3)0.7571 (4)0.68168 (19)0.0214 (4)
H50.23660.71930.60490.026*
C60.4554 (3)0.6303 (3)0.72981 (19)0.0175 (4)
C70.4806 (3)0.4437 (3)0.6638 (2)0.0188 (4)
H70.40190.40710.58680.023*
C80.6349 (3)0.1448 (3)0.64566 (19)0.0184 (4)
C90.7588 (3)−0.1475 (3)0.61665 (18)0.0178 (4)
C100.8777 (3)−0.3090 (4)0.6428 (2)0.0228 (4)
H100.9681−0.30560.71700.027*
C110.8612 (3)−0.4729 (4)0.5589 (2)0.0249 (5)
H110.9414−0.58320.57570.030*
C120.7290 (3)−0.4798 (4)0.4498 (2)0.0229 (5)
H120.7212−0.59390.39310.027*
C130.6081 (3)−0.3219 (4)0.4225 (2)0.0213 (4)
H130.5170−0.32770.34880.026*
C140.6257 (3)−0.1556 (3)0.5070 (2)0.0190 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0181 (2)0.0172 (2)0.0187 (2)−0.0003 (2)0.00322 (17)−0.00262 (19)
O10.0216 (9)0.0314 (10)0.0232 (9)0.0063 (7)−0.0024 (7)−0.0064 (6)
N10.0193 (8)0.0166 (8)0.0183 (8)−0.0016 (7)0.0040 (7)−0.0015 (7)
N20.0222 (10)0.0148 (8)0.0191 (9)−0.0020 (7)0.0042 (7)−0.0008 (7)
C10.0181 (10)0.0220 (10)0.0181 (9)−0.0008 (8)0.0051 (8)−0.0004 (8)
C20.0235 (11)0.0215 (10)0.0211 (10)−0.0032 (9)0.0066 (9)−0.0052 (8)
C30.0265 (12)0.0193 (10)0.0263 (11)−0.0017 (9)0.0144 (9)−0.0023 (8)
C40.0228 (12)0.0211 (11)0.0255 (11)0.0054 (8)0.0095 (9)0.0051 (8)
C50.0197 (10)0.0245 (10)0.0190 (9)0.0002 (9)0.0048 (8)0.0025 (8)
C60.0179 (10)0.0178 (9)0.0164 (9)−0.0011 (8)0.0050 (8)−0.0012 (8)
C70.0173 (10)0.0200 (11)0.0177 (10)−0.0029 (8)0.0035 (8)−0.0002 (7)
C80.0196 (10)0.0168 (10)0.0182 (9)−0.0025 (8)0.0051 (8)0.0001 (7)
C90.0221 (10)0.0148 (9)0.0175 (9)−0.0025 (8)0.0077 (8)−0.0021 (8)
C100.0228 (11)0.0209 (10)0.0249 (10)0.0016 (9)0.0081 (8)0.0032 (8)
C110.0245 (12)0.0224 (11)0.0311 (12)0.0032 (9)0.0136 (10)0.0047 (9)
C120.0282 (13)0.0182 (10)0.0276 (12)−0.0036 (9)0.0166 (10)−0.0058 (9)
C130.0205 (10)0.0224 (11)0.0208 (10)−0.0043 (9)0.0063 (8)−0.0018 (8)
C140.0178 (10)0.0156 (9)0.0249 (10)0.0012 (8)0.0088 (8)0.0022 (8)

Geometric parameters (Å, °)

S1—C141.733 (2)C4—H40.9500
S1—C81.770 (2)C5—C61.400 (3)
O1—C11.345 (3)C5—H50.9500
O1—H10.8672C6—C71.442 (3)
N1—C71.294 (3)C7—H70.9500
N1—C81.389 (3)C9—C101.399 (3)
N2—C81.286 (3)C9—C141.402 (3)
N2—C91.394 (3)C10—C111.378 (3)
C1—C21.393 (3)C10—H100.9500
C1—C61.410 (3)C11—C121.393 (4)
C2—C31.383 (4)C11—H110.9500
C2—H20.9500C12—C131.395 (3)
C3—C41.394 (4)C12—H120.9500
C3—H30.9500C13—C141.392 (3)
C4—C51.381 (3)C13—H130.9500
C14—S1—C888.21 (11)N1—C7—H7119.7
C1—O1—H1102.4C6—C7—H7119.7
C7—N1—C8121.20 (18)N2—C8—N1119.83 (19)
C8—N2—C9109.65 (18)N2—C8—S1116.81 (16)
O1—C1—C2118.56 (19)N1—C8—S1123.36 (17)
O1—C1—C6121.8 (2)N2—C9—C10124.3 (2)
C2—C1—C6119.7 (2)N2—C9—C14115.84 (19)
C3—C2—C1120.4 (2)C10—C9—C14119.9 (2)
C3—C2—H2119.8C11—C10—C9118.8 (2)
C1—C2—H2119.8C11—C10—H10120.6
C2—C3—C4120.3 (2)C9—C10—H10120.6
C2—C3—H3119.8C10—C11—C12121.1 (2)
C4—C3—H3119.8C10—C11—H11119.4
C5—C4—C3119.7 (2)C12—C11—H11119.4
C5—C4—H4120.2C13—C12—C11121.1 (2)
C3—C4—H4120.2C13—C12—H12119.5
C4—C5—C6121.0 (2)C11—C12—H12119.5
C4—C5—H5119.5C14—C13—C12117.7 (2)
C6—C5—H5119.5C14—C13—H13121.2
C5—C6—C1118.87 (19)C12—C13—H13121.2
C5—C6—C7120.47 (19)C13—C14—C9121.5 (2)
C1—C6—C7120.7 (2)C13—C14—S1129.07 (18)
N1—C7—C6120.7 (2)C9—C14—S1109.47 (16)
O1—C1—C2—C3−178.7 (2)C14—S1—C8—N21.30 (18)
C6—C1—C2—C31.4 (3)C14—S1—C8—N1−178.28 (18)
C1—C2—C3—C40.2 (4)C8—N2—C9—C10−179.1 (2)
C2—C3—C4—C5−1.2 (4)C8—N2—C9—C140.2 (3)
C3—C4—C5—C60.6 (3)N2—C9—C10—C11179.7 (2)
C4—C5—C6—C10.9 (3)C14—C9—C10—C110.4 (3)
C4—C5—C6—C7−180.0 (2)C9—C10—C11—C12−0.1 (3)
O1—C1—C6—C5178.2 (2)C10—C11—C12—C13−0.6 (4)
C2—C1—C6—C5−1.9 (3)C11—C12—C13—C141.1 (3)
O1—C1—C6—C7−0.9 (3)C12—C13—C14—C9−0.8 (3)
C2—C1—C6—C7179.0 (2)C12—C13—C14—S1179.15 (17)
C8—N1—C7—C6179.8 (2)N2—C9—C14—C13−179.33 (19)
C5—C6—C7—N1−179.6 (2)C10—C9—C14—C130.0 (3)
C1—C6—C7—N1−0.5 (3)N2—C9—C14—S10.7 (2)
C9—N2—C8—N1178.51 (18)C10—C9—C14—S1−179.89 (17)
C9—N2—C8—S1−1.1 (2)C8—S1—C14—C13179.0 (2)
C7—N1—C8—N2−177.6 (2)C8—S1—C14—C9−1.04 (16)
C7—N1—C8—S12.0 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.871.732.550 (2)156

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2043).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Liu, S.-Q., Bi, C.-F., Chen, L.-Y. & Fan, Y.-H. (2009). Acta Cryst. E65, o738. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43 Submitted.

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