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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o1974.
Published online 2008 September 20. doi:  10.1107/S1600536808029644
PMCID: PMC2959411

2-[(2-Hydr­oxy-1-naphth­yl)methyl­ene­amino]-1,3-benzothia­zole

Abstract

In the title compound, C18H12N2OS, the dihedral angle between the mean planes of the aromatic ring systems is 7.26 (8)°. There is an intra­molecular O—H(...)N hydrogen bond, forming a six-membered ring. In the crystal structure, inter­molecular C—H(...)N hydrogen bonds link the mol­ecules into a one-dimensional chain.

Related literature

For general background, see: Lindoy et al. (1976 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1974-scheme1.jpg

Experimental

Crystal data

  • C18H12N2OS
  • M r = 304.36
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1974-efi1.jpg
  • a = 9.7439 (13) Å
  • b = 15.1506 (16) Å
  • c = 9.8082 (14) Å
  • β = 101.788 (2)°
  • V = 1417.4 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 293 (2) K
  • 0.29 × 0.24 × 0.16 mm

Data collection

  • Siemens SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.936, T max = 0.964
  • 6948 measured reflections
  • 2493 independent reflections
  • 1492 reflections with I > 2σ(I)
  • R int = 0.048

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.122
  • S = 1.06
  • 2493 reflections
  • 199 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808029644/sg2264sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029644/sg2264Isup2.hkl

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

Acknowledgments

We acknowledge the National Natural Foundation of China (grant No. 20771053) and the Natural Science Foundation of Shandong Province (2005ZX09) for financial support. This work is also partially supported by the Shandong ‘Tai-Shan Scholar Research Fund’.

supplementary crystallographic information

Comment

Schiff bases are known to be important due to their applications in the preparation of dyes, liquid crystals and powerful corrosion inhibitors. Further more, they are used in the mechanism of many biochemical processes (Lindoy et al., 1976). We report here the synthesis and crystal structure of the title compound, a new Schiff base compound.

The molecular structure of the title compound is shown in Fig. 1. This compound is nonplanar, with a dihedral angle of 7.39 (5)° between the two benzene rings. There exists an intramolecular O—H···N hydrogen bond, forming a six-membered ring. An E configuration with respect to the C?N bond is shown by the molecule, with a C—N?C—C torsoin angle of 178.8 (2)°.

As seen in Fig.2, the molecules are linked into a one-dimensional chain by intermolecular C—H···N hydrogen bonds (Table 1).

Experimental

A mixture of 2-aminobenzothiazole (1 mmol) and 2-hydroxy-1-naphthaldehyde (1 mmol) in absolute ethanol (15 ml) was heated under reflux with stirring for 5 h and then filtered. The resulting clear orange solution was diffused diethyl ether vapor at room temperature for 16 days, after which large orange block-shaped crystals of the title complex suitable for X-ray diffraction analysis were obtained.

Refinement

All H-atoms were positioned geometrically and refined using a riding model, with C—H = 0.96 Å (methylene) or 0.93 Å (aromatic), 0.82 Å (hydroxyl) and Uiso(H) =1.2Ueq(C).

Figures

Fig. 1.
The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
Fig. 2.
The crystal packing of the title compound, viewed approximately along the c axis.

Crystal data

C18H12N2OSF(000) = 632
Mr = 304.36Dx = 1.426 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1399 reflections
a = 9.7439 (13) Åθ = 2.5–24.1°
b = 15.1506 (16) ŵ = 0.23 mm1
c = 9.8082 (14) ÅT = 293 K
β = 101.788 (2)°Block, orange
V = 1417.4 (3) Å30.29 × 0.24 × 0.16 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer2493 independent reflections
Radiation source: fine-focus sealed tube1492 reflections with I > 2σ(I)
graphiteRint = 0.048
[var phi] and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −6→11
Tmin = 0.936, Tmax = 0.964k = −18→16
6948 measured reflectionsl = −10→11

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0495P)2 + 0.1122P] where P = (Fo2 + 2Fc2)/3
2493 reflections(Δ/σ)max = 0.001
199 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = −0.27 e Å3

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.
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.

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

xyzUiso*/Ueq
N10.1366 (2)0.12262 (16)1.0288 (2)0.0448 (6)
N20.2042 (2)−0.00510 (15)0.9113 (2)0.0411 (6)
O10.2722 (2)−0.14394 (13)0.7886 (2)0.0557 (6)
H10.2814−0.10330.84500.084*
S10.39272 (8)0.06918 (6)1.12063 (8)0.0516 (3)
C10.0880 (3)−0.00369 (18)0.8179 (3)0.0392 (7)
H1A0.02450.04160.82180.047*
C20.0532 (3)−0.06771 (18)0.7105 (3)0.0345 (7)
C30.1482 (3)−0.13637 (19)0.6999 (3)0.0412 (7)
C40.1156 (3)−0.20068 (19)0.5945 (3)0.0474 (8)
H40.1790−0.24570.58870.057*
C5−0.0075 (3)−0.19716 (19)0.5022 (3)0.0468 (8)
H5−0.0275−0.24080.43430.056*
C6−0.1079 (3)−0.12922 (18)0.5045 (3)0.0386 (7)
C7−0.0773 (3)−0.06359 (18)0.6093 (3)0.0340 (7)
C8−0.1789 (3)0.00355 (18)0.6076 (3)0.0435 (8)
H8−0.16260.04790.67460.052*
C9−0.3009 (3)0.0043 (2)0.5089 (3)0.0520 (9)
H9−0.36570.04930.51000.062*
C10−0.3298 (3)−0.0610 (2)0.4072 (3)0.0536 (9)
H10−0.4131−0.05980.34090.064*
C11−0.2348 (3)−0.1267 (2)0.4058 (3)0.0499 (8)
H11−0.2542−0.17060.33840.060*
C120.2275 (3)0.06286 (19)1.0103 (3)0.0407 (7)
C130.1972 (3)0.18005 (19)1.1355 (3)0.0395 (7)
C140.3359 (3)0.16080 (19)1.1995 (3)0.0417 (7)
C150.4076 (3)0.2139 (2)1.3077 (3)0.0507 (8)
H150.50000.20181.35020.061*
C160.3372 (4)0.2847 (2)1.3493 (3)0.0535 (9)
H160.38280.32051.42140.064*
C170.1997 (3)0.3034 (2)1.2859 (3)0.0526 (8)
H170.15510.35171.31620.063*
C180.1283 (3)0.2523 (2)1.1798 (3)0.0474 (8)
H180.03600.26541.13800.057*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0401 (15)0.0450 (16)0.0464 (15)−0.0018 (12)0.0022 (12)−0.0040 (13)
N20.0439 (15)0.0404 (16)0.0376 (14)−0.0009 (11)0.0051 (11)−0.0026 (12)
O10.0471 (14)0.0532 (14)0.0624 (14)0.0129 (10)0.0010 (11)−0.0064 (11)
S10.0419 (5)0.0566 (6)0.0521 (5)0.0031 (4)−0.0004 (4)−0.0015 (4)
C10.0415 (18)0.0363 (18)0.0411 (17)0.0000 (13)0.0114 (14)0.0002 (14)
C20.0372 (17)0.0296 (16)0.0380 (16)−0.0015 (13)0.0111 (13)−0.0003 (14)
C30.0397 (19)0.0419 (19)0.0424 (17)−0.0002 (14)0.0094 (14)0.0024 (15)
C40.051 (2)0.0388 (19)0.055 (2)0.0061 (14)0.0168 (16)−0.0046 (16)
C50.057 (2)0.040 (2)0.0458 (18)−0.0065 (15)0.0164 (16)−0.0090 (15)
C60.0416 (18)0.0380 (18)0.0370 (17)−0.0061 (14)0.0097 (14)0.0037 (14)
C70.0389 (17)0.0304 (16)0.0355 (15)−0.0019 (13)0.0141 (13)0.0042 (13)
C80.0469 (19)0.0368 (19)0.0482 (18)−0.0008 (14)0.0130 (15)−0.0016 (14)
C90.040 (2)0.051 (2)0.063 (2)0.0078 (15)0.0045 (16)0.0094 (18)
C100.045 (2)0.061 (2)0.0485 (19)−0.0102 (17)−0.0051 (15)0.0084 (18)
C110.057 (2)0.046 (2)0.0450 (19)−0.0123 (16)0.0061 (16)−0.0008 (16)
C120.0388 (18)0.0401 (18)0.0422 (17)−0.0010 (14)0.0057 (14)0.0049 (16)
C130.0413 (18)0.0428 (19)0.0341 (16)−0.0054 (14)0.0072 (14)0.0033 (14)
C140.0399 (18)0.0445 (19)0.0403 (16)−0.0066 (14)0.0069 (14)0.0080 (15)
C150.046 (2)0.059 (2)0.0432 (18)−0.0085 (16)0.0008 (15)0.0042 (17)
C160.066 (2)0.049 (2)0.0438 (19)−0.0179 (17)0.0057 (17)−0.0044 (16)
C170.064 (2)0.042 (2)0.053 (2)−0.0047 (16)0.0144 (17)0.0001 (16)
C180.0431 (19)0.048 (2)0.0494 (19)−0.0001 (15)0.0060 (15)0.0004 (16)

Geometric parameters (Å, °)

N1—C121.305 (3)C7—C81.417 (4)
N1—C131.396 (3)C8—C91.371 (4)
N2—C11.303 (3)C8—H80.9300
N2—C121.402 (3)C9—C101.393 (4)
O1—C31.342 (3)C9—H90.9300
O1—H10.8200C10—C111.360 (4)
S1—C141.734 (3)C10—H100.9300
S1—C121.749 (3)C11—H110.9300
C1—C21.421 (4)C13—C141.399 (4)
C1—H1A0.9300C13—C181.400 (4)
C2—C31.410 (4)C14—C151.399 (4)
C2—C71.446 (3)C15—C161.380 (4)
C3—C41.409 (4)C15—H150.9300
C4—C51.348 (4)C16—C171.386 (4)
C4—H40.9300C16—H160.9300
C5—C61.424 (4)C17—C181.368 (4)
C5—H50.9300C17—H170.9300
C6—C111.407 (4)C18—H180.9300
C6—C71.417 (4)
C12—N1—C13110.0 (2)C8—C9—H9119.4
C1—N2—C12118.0 (2)C10—C9—H9119.4
C3—O1—H1109.5C11—C10—C9119.2 (3)
C14—S1—C1288.99 (14)C11—C10—H10120.4
N2—C1—C2123.5 (3)C9—C10—H10120.4
N2—C1—H1A118.3C10—C11—C6121.2 (3)
C2—C1—H1A118.3C10—C11—H11119.4
C3—C2—C1119.8 (3)C6—C11—H11119.4
C3—C2—C7118.6 (2)N1—C12—N2126.0 (3)
C1—C2—C7121.5 (2)N1—C12—S1116.2 (2)
O1—C3—C2122.2 (3)N2—C12—S1117.9 (2)
O1—C3—C4117.1 (3)N1—C13—C14115.3 (3)
C2—C3—C4120.8 (3)N1—C13—C18124.4 (3)
C5—C4—C3120.1 (3)C14—C13—C18120.3 (3)
C5—C4—H4119.9C15—C14—C13120.5 (3)
C3—C4—H4119.9C15—C14—S1130.0 (2)
C4—C5—C6122.5 (3)C13—C14—S1109.5 (2)
C4—C5—H5118.7C16—C15—C14118.0 (3)
C6—C5—H5118.7C16—C15—H15121.0
C11—C6—C7120.3 (3)C14—C15—H15121.0
C11—C6—C5121.3 (3)C15—C16—C17121.3 (3)
C7—C6—C5118.4 (3)C15—C16—H16119.3
C8—C7—C6116.9 (2)C17—C16—H16119.3
C8—C7—C2123.6 (2)C18—C17—C16121.4 (3)
C6—C7—C2119.5 (2)C18—C17—H17119.3
C9—C8—C7121.1 (3)C16—C17—H17119.3
C9—C8—H8119.4C17—C18—C13118.5 (3)
C7—C8—H8119.4C17—C18—H18120.8
C8—C9—C10121.3 (3)C13—C18—H18120.8
C12—N2—C1—C2178.8 (2)C9—C10—C11—C6−0.5 (4)
N2—C1—C2—C3−1.2 (4)C7—C6—C11—C100.9 (4)
N2—C1—C2—C7179.9 (2)C5—C6—C11—C10−179.1 (3)
C1—C2—C3—O10.1 (4)C13—N1—C12—N2−179.4 (2)
C7—C2—C3—O1179.1 (2)C13—N1—C12—S10.8 (3)
C1—C2—C3—C4179.8 (2)C1—N2—C12—N18.5 (4)
C7—C2—C3—C4−1.3 (4)C1—N2—C12—S1−171.67 (19)
O1—C3—C4—C5179.8 (2)C14—S1—C12—N1−0.1 (2)
C2—C3—C4—C50.1 (4)C14—S1—C12—N2−180.0 (2)
C3—C4—C5—C61.0 (4)C12—N1—C13—C14−1.3 (3)
C4—C5—C6—C11179.3 (3)C12—N1—C13—C18179.0 (3)
C4—C5—C6—C7−0.8 (4)N1—C13—C14—C15179.9 (2)
C11—C6—C7—C8−0.7 (3)C18—C13—C14—C15−0.4 (4)
C5—C6—C7—C8179.3 (2)N1—C13—C14—S11.2 (3)
C11—C6—C7—C2179.5 (2)C18—C13—C14—S1−179.1 (2)
C5—C6—C7—C2−0.5 (3)C12—S1—C14—C15−179.1 (3)
C3—C2—C7—C8−178.3 (2)C12—S1—C14—C13−0.56 (19)
C1—C2—C7—C80.7 (4)C13—C14—C15—C160.5 (4)
C3—C2—C7—C61.4 (3)S1—C14—C15—C16178.9 (2)
C1—C2—C7—C6−179.6 (2)C14—C15—C16—C17−0.3 (4)
C6—C7—C8—C90.1 (4)C15—C16—C17—C180.1 (4)
C2—C7—C8—C9179.9 (2)C16—C17—C18—C130.0 (4)
C7—C8—C9—C100.3 (4)N1—C13—C18—C17179.9 (2)
C8—C9—C10—C11−0.1 (4)C14—C13—C18—C170.2 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C16—H16···N1i0.932.633.389 (4)140.
O1—H1···N20.821.852.576 (2)148.

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2264).

References

  • Lindoy, L. F., Lip, H. C., Power, L. F. & Rea, T. H. (1976). Inorg. Chem.15, 1724–1727.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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