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ISSN: 2056-9890

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

aChemistry Department, Faculty of Science, King Abdul Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 16 June 2010; accepted 19 June 2010; online 26 June 2010)

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[Liu, S.-Q., Bi, C.-F., Chen, L.-Y. & Fan, Y.-H. (2009). Acta Cryst. E65, o738.]). Acta Cryst. E65, o738].

Related literature

For an ortho­rhom­bic modification of this structure, see: Liu et al. (2009[Liu, S.-Q., Bi, C.-F., Chen, L.-Y. & Fan, Y.-H. (2009). Acta Cryst. E65, o738.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10N2OS

  • Mr = 254.30

  • Monoclinic, P n

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.964, Tmax = 0.979

  • 5307 measured reflections

  • 2599 independent reflections

  • 2512 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1242 Friedel pairs

  • Flack parameter: 0.27 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N1 0.87 1.73 2.550 (2) 156

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.]).

Supporting information


Comment top

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.

Related literature top

For the orthorhombic modification, see: Liu et al. (2009).

Experimental top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C14H10N2OS at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
2-[(1,3-benzothiazol-2-yl)iminomethyl]phenol top
Crystal data top
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 top
Bruker SMART APEX
diffractometer
2599 independent reflections
Radiation source: fine-focus sealed tube2512 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1110
Tmin = 0.964, Tmax = 0.979k = 88
5307 measured reflectionsl = 1414
Refinement top
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) = 0.110 w = 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 methodsAbsolute structure parameter: 0.27 (8)
Crystal data top
C14H10N2OSV = 582.97 (6) Å3
Mr = 254.30Z = 2
Monoclinic, PnMo Kα radiation
a = 8.6391 (4) ŵ = 0.26 mm1
b = 6.2313 (4) ÅT = 100 K
c = 11.4459 (8) Å0.14 × 0.13 × 0.08 mm
β = 108.893 (1)°
Data collection top
Bruker SMART APEX
diffractometer
2599 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2512 reflections with I > 2σ(I)
Tmin = 0.964, Tmax = 0.979Rint = 0.029
5307 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.110Δρmax = 0.40 e Å3
S = 1.05Δρmin = 0.25 e Å3
2599 reflectionsAbsolute structure: Flack (1983), 1242 Friedel pairs
164 parametersAbsolute structure parameter: 0.27 (8)
2 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
H100.96810.30560.71700.027*
C110.8612 (3)0.4729 (4)0.5589 (2)0.0249 (5)
H110.94140.58320.57570.030*
C120.7290 (3)0.4798 (4)0.4498 (2)0.0229 (5)
H120.72120.59390.39310.027*
C130.6081 (3)0.3219 (4)0.4225 (2)0.0213 (4)
H130.51700.32770.34880.026*
C140.6257 (3)0.1556 (3)0.5070 (2)0.0190 (4)
Atomic displacement parameters (Å2) top
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, º) top
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—C3178.7 (2)C14—S1—C8—N21.30 (18)
C6—C1—C2—C31.4 (3)C14—S1—C8—N1178.28 (18)
C1—C2—C3—C40.2 (4)C8—N2—C9—C10179.1 (2)
C2—C3—C4—C51.2 (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—C7180.0 (2)C9—C10—C11—C120.1 (3)
O1—C1—C6—C5178.2 (2)C10—C11—C12—C130.6 (4)
C2—C1—C6—C51.9 (3)C11—C12—C13—C141.1 (3)
O1—C1—C6—C70.9 (3)C12—C13—C14—C90.8 (3)
C2—C1—C6—C7179.0 (2)C12—C13—C14—S1179.15 (17)
C8—N1—C7—C6179.8 (2)N2—C9—C14—C13179.33 (19)
C5—C6—C7—N1179.6 (2)C10—C9—C14—C130.0 (3)
C1—C6—C7—N10.5 (3)N2—C9—C14—S10.7 (2)
C9—N2—C8—N1178.51 (18)C10—C9—C14—S1179.89 (17)
C9—N2—C8—S11.1 (2)C8—S1—C14—C13179.0 (2)
C7—N1—C8—N2177.6 (2)C8—S1—C14—C91.04 (16)
C7—N1—C8—S12.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.871.732.550 (2)156

Experimental details

Crystal data
Chemical formulaC14H10N2OS
Mr254.30
Crystal system, space groupMonoclinic, Pn
Temperature (K)100
a, b, c (Å)8.6391 (4), 6.2313 (4), 11.4459 (8)
β (°) 108.893 (1)
V3)582.97 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.26
Crystal size (mm)0.14 × 0.13 × 0.08
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.964, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
5307, 2599, 2512
Rint0.029
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.110, 1.05
No. of reflections2599
No. of parameters164
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.25
Absolute structureFlack (1983), 1242 Friedel pairs
Absolute structure parameter0.27 (8)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.871.732.550 (2)156
 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationLiu, S.-Q., Bi, C.-F., Chen, L.-Y. & Fan, Y.-H. (2009). Acta Cryst. E65, o738.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.  Google Scholar

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