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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o832.
Published online 2009 March 25. doi:  10.1107/S1600536809009337
PMCID: PMC2969048

(E)-2-[(6-Ethoxy­benzothia­zol-2-yl)imino­meth­yl]-6-methoxy­phenol

Abstract

In the title mol­ecule, C17H16N2O3S, the benzothia­zole fragment and the benzene ring form a dihedral angle of 13.8 (4)°, and an intramolecular O—H(...)N hydrogen bond occurs. In the crystal structure, pairs of weak inter­molecular O—H(...)S and C—H(...)(O,O) hydrogen bonds link mol­ecules into centrosymmetric dimers. These dimers are related by translation along the a axis and form stacks via π–π inter­actions, with a short inter­molecular distance of 3.766 (5) Å between the centroids of the benzene and thia­zole rings.

Related literature

For a related crystal structure, see: Zhao et al. (2008 [triangle]). For details of the crystallography and coordination chemistry of Schiff base compounds, see: Garnovski et al. (1993 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o832-scheme1.jpg

Experimental

Crystal data

  • C17H16N2O3S
  • M r = 328.38
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o832-efi1.jpg
  • a = 6.0178 (14) Å
  • b = 10.941 (3) Å
  • c = 12.164 (3) Å
  • α = 85.479 (4)°
  • β = 83.693 (5)°
  • γ = 76.486 (3)°
  • V = 772.9 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 298 K
  • 0.12 × 0.08 × 0.06 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.973, T max = 0.987
  • 4102 measured reflections
  • 2720 independent reflections
  • 1911 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.114
  • S = 1.03
  • 2720 reflections
  • 209 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.21 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 global, I. DOI: 10.1107/S1600536809009337/cv2526sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009337/cv2526Isup2.hkl

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

Acknowledgments

The author is grateful for financial support from the Natural Science Foundation of Dongchang College of Liaocheng University (grant No. LG0801).

supplementary crystallographic information

Comment

Recently, a number of Schiff base compounds have been investigated in terms of their crystallography and coordination chemistry (Garnovski et al., 1993). In order to continue our studies on Schiff bases, we now report the synthesis and crystal structure of the title compound, (I).

In (I) (Fig. 1), all the geometric parameters are in a good agreement with those found in (E)-2-methoxy-6-[(5-methylisoxazol-3-yl)-iminomethyl] phenol (Zhao et al., 2008). The benzene and the benzothiazole rings make a dihedral angle of 13.8 (4)° showing that the Schiff base ligand adopts a non-planar conformation in the case. Moreover, weak intermolecular O—H···S and C—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers. These dimers related by translation along axis a form stacks viaπ–π interactions proved by short intermolecular distance of 3.766 (5) Å between the centroids of benzene and thiazole rings.

Experimental

The title compound was synthesized by the reaction of 2-hydroxy-3-methoxybenzaldehyde (0.152 g, 1 mmol) and 6-ethoxybenzothiazol-2-amine (0.194 g, 1 mmol) in ethanol solution and stirred under reflux conditions (353 K) for 5 h. When cooled to room temperature the solution was filtered and after a week yellow crystals suitable for X-ray diffraction study were obtained. Yield, 0.283 g, 86%. m.p. 342–344 K.

Refinement

The H atoms were included in the riding-model approximation with C—H = 0.93 Å, C—H = 0.96 Å and O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C-aromatic) and Uiso(H) = 1.5Ueq(C-methyl, methylene and O).

Figures

Fig. 1.
The molecular structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Crystal data

C17H16N2O3SZ = 2
Mr = 328.38F(000) = 344
Triclinic, P1Dx = 1.411 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.0178 (14) ÅCell parameters from 982 reflections
b = 10.941 (3) Åθ = 2.6–22.3°
c = 12.164 (3) ŵ = 0.23 mm1
α = 85.479 (4)°T = 298 K
β = 83.693 (5)°Block, yellow
γ = 76.486 (3)°0.12 × 0.08 × 0.06 mm
V = 772.9 (3) Å3

Data collection

Bruker SMART APEX diffractometer2720 independent reflections
Radiation source: fine-focus sealed tube1911 reflections with I > 2σ(I)
graphiteRint = 0.020
[var phi] and ω scansθmax = 25.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→7
Tmin = 0.973, Tmax = 0.987k = −12→12
4102 measured reflectionsl = −14→9

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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0548P)2 + 0.0301P] where P = (Fo2 + 2Fc2)/3
2720 reflections(Δ/σ)max < 0.001
209 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.21 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
S10.46082 (11)0.40652 (6)0.37670 (5)0.0489 (2)
O10.8898 (3)0.68081 (19)0.43648 (14)0.0622 (5)
H10.81200.63630.41570.093*
O21.1451 (3)0.83142 (17)0.47463 (15)0.0609 (5)
O3−0.0448 (3)0.15300 (16)0.22235 (13)0.0528 (5)
N10.7555 (3)0.54862 (17)0.29849 (16)0.0439 (5)
N20.5822 (3)0.45416 (18)0.16878 (16)0.0447 (5)
C11.0271 (4)0.7137 (2)0.3503 (2)0.0437 (6)
C21.0358 (4)0.6701 (2)0.2444 (2)0.0413 (6)
C31.1832 (4)0.7085 (2)0.1588 (2)0.0498 (7)
H31.19150.67870.08860.060*
C41.3155 (4)0.7898 (2)0.1772 (2)0.0539 (7)
H41.41110.81610.11940.065*
C51.3068 (4)0.8329 (2)0.2824 (2)0.0518 (7)
H51.39780.88770.29450.062*
C61.1657 (4)0.7957 (2)0.3686 (2)0.0458 (6)
C71.2911 (5)0.9082 (3)0.5008 (2)0.0687 (9)
H7A1.44840.86680.48220.103*
H7B1.26680.92210.57860.103*
H7C1.25660.98760.45930.103*
C80.8943 (4)0.5867 (2)0.2223 (2)0.0436 (6)
H80.90360.55960.15110.052*
C90.6154 (4)0.4739 (2)0.2685 (2)0.0413 (6)
C100.4252 (4)0.3792 (2)0.17276 (19)0.0406 (6)
C110.3392 (4)0.3421 (2)0.27927 (19)0.0397 (6)
C120.1811 (4)0.2670 (2)0.2947 (2)0.0418 (6)
H120.12460.24350.36550.050*
C130.1098 (4)0.2280 (2)0.2018 (2)0.0423 (6)
C140.1905 (4)0.2659 (2)0.0958 (2)0.0473 (6)
H140.13940.23940.03430.057*
C150.3456 (4)0.3422 (2)0.0812 (2)0.0477 (6)
H150.39630.36860.01030.057*
C16−0.1092 (4)0.1015 (2)0.1306 (2)0.0520 (7)
H16A0.02530.05160.09050.062*
H16B−0.18270.16840.08050.062*
C17−0.2723 (4)0.0206 (2)0.1744 (2)0.0595 (8)
H17A−0.1959−0.04720.22160.089*
H17B−0.3230−0.01330.11370.089*
H17C−0.40230.07030.21600.089*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0572 (4)0.0570 (4)0.0411 (4)−0.0323 (3)−0.0019 (3)0.0001 (3)
O10.0725 (13)0.0819 (14)0.0470 (11)−0.0529 (11)0.0118 (9)−0.0104 (10)
O20.0722 (13)0.0712 (12)0.0521 (11)−0.0419 (10)−0.0002 (9)−0.0115 (10)
O30.0598 (11)0.0620 (11)0.0476 (10)−0.0381 (9)0.0015 (8)−0.0062 (9)
N10.0431 (11)0.0474 (12)0.0461 (12)−0.0220 (10)−0.0008 (10)−0.0009 (10)
N20.0443 (12)0.0506 (12)0.0429 (12)−0.0211 (10)0.0007 (9)−0.0006 (10)
C10.0410 (13)0.0452 (14)0.0464 (15)−0.0183 (12)0.0033 (11)0.0027 (12)
C20.0393 (13)0.0419 (14)0.0443 (14)−0.0154 (11)−0.0021 (11)0.0033 (11)
C30.0490 (15)0.0566 (16)0.0474 (15)−0.0225 (13)0.0015 (12)−0.0016 (13)
C40.0519 (16)0.0616 (17)0.0519 (16)−0.0289 (14)0.0097 (13)0.0014 (14)
C50.0498 (15)0.0530 (16)0.0602 (17)−0.0306 (13)0.0020 (13)−0.0012 (14)
C60.0473 (14)0.0462 (14)0.0473 (15)−0.0183 (12)−0.0024 (12)−0.0025 (12)
C70.081 (2)0.0717 (19)0.0689 (19)−0.0453 (17)−0.0054 (16)−0.0165 (16)
C80.0402 (13)0.0486 (15)0.0432 (14)−0.0146 (12)0.0006 (11)−0.0032 (12)
C90.0391 (13)0.0418 (14)0.0453 (15)−0.0158 (11)−0.0010 (11)−0.0010 (12)
C100.0390 (13)0.0435 (14)0.0418 (14)−0.0177 (11)0.0031 (11)−0.0028 (11)
C110.0414 (13)0.0401 (13)0.0394 (13)−0.0140 (11)−0.0008 (11)−0.0035 (11)
C120.0450 (14)0.0446 (14)0.0390 (13)−0.0208 (12)0.0046 (11)−0.0012 (11)
C130.0403 (13)0.0423 (14)0.0475 (15)−0.0181 (11)0.0011 (11)−0.0024 (12)
C140.0487 (15)0.0580 (16)0.0409 (14)−0.0245 (13)0.0004 (11)−0.0070 (12)
C150.0490 (15)0.0600 (16)0.0381 (14)−0.0248 (13)0.0042 (11)−0.0014 (12)
C160.0538 (16)0.0576 (16)0.0527 (16)−0.0279 (13)−0.0038 (13)−0.0075 (13)
C170.0587 (17)0.0564 (17)0.0731 (19)−0.0333 (14)−0.0030 (15)−0.0058 (15)

Geometric parameters (Å, °)

S1—C111.732 (2)C5—H50.9300
S1—C91.743 (2)C7—H7A0.9600
O1—C11.342 (3)C7—H7B0.9600
O1—H10.8200C7—H7C0.9600
O2—C61.361 (3)C8—H80.9300
O2—C71.425 (3)C10—C151.383 (3)
O3—C131.370 (3)C10—C111.407 (3)
O3—C161.417 (3)C11—C121.385 (3)
N1—C81.289 (3)C12—C131.382 (3)
N1—C91.396 (3)C12—H120.9300
N2—C91.293 (3)C13—C141.394 (3)
N2—C101.383 (3)C14—C151.380 (3)
C1—C21.399 (3)C14—H140.9300
C1—C61.405 (3)C15—H150.9300
C2—C31.397 (3)C16—C171.500 (3)
C2—C81.443 (3)C16—H16A0.9700
C3—C41.370 (3)C16—H16B0.9700
C3—H30.9300C17—H17A0.9600
C4—C51.390 (4)C17—H17B0.9600
C4—H40.9300C17—H17C0.9600
C5—C61.373 (3)
C11—S1—C988.69 (11)N2—C9—N1126.4 (2)
C1—O1—H1109.5N2—C9—S1117.12 (17)
C6—O2—C7117.7 (2)N1—C9—S1116.38 (18)
C13—O3—C16117.82 (18)C15—C10—N2124.9 (2)
C8—N1—C9118.2 (2)C15—C10—C11119.1 (2)
C9—N2—C10109.4 (2)N2—C10—C11115.9 (2)
O1—C1—C2122.7 (2)C12—C11—C10121.7 (2)
O1—C1—C6117.7 (2)C12—C11—S1129.48 (19)
C2—C1—C6119.6 (2)C10—C11—S1108.82 (16)
C3—C2—C1119.4 (2)C13—C12—C11118.0 (2)
C3—C2—C8119.6 (2)C13—C12—H12121.0
C1—C2—C8121.1 (2)C11—C12—H12121.0
C4—C3—C2120.6 (2)O3—C13—C12115.4 (2)
C4—C3—H3119.7O3—C13—C14123.7 (2)
C2—C3—H3119.7C12—C13—C14120.9 (2)
C3—C4—C5120.0 (2)C15—C14—C13120.6 (2)
C3—C4—H4120.0C15—C14—H14119.7
C5—C4—H4120.0C13—C14—H14119.7
C6—C5—C4120.8 (2)C14—C15—C10119.6 (2)
C6—C5—H5119.6C14—C15—H15120.2
C4—C5—H5119.6C10—C15—H15120.2
O2—C6—C5125.7 (2)O3—C16—C17107.7 (2)
O2—C6—C1114.7 (2)O3—C16—H16A110.2
C5—C6—C1119.7 (2)C17—C16—H16A110.2
O2—C7—H7A109.5O3—C16—H16B110.2
O2—C7—H7B109.5C17—C16—H16B110.2
H7A—C7—H7B109.5H16A—C16—H16B108.5
O2—C7—H7C109.5C16—C17—H17A109.5
H7A—C7—H7C109.5C16—C17—H17B109.5
H7B—C7—H7C109.5H17A—C17—H17B109.5
N1—C8—C2121.9 (2)C16—C17—H17C109.5
N1—C8—H8119.0H17A—C17—H17C109.5
C2—C8—H8119.0H17B—C17—H17C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.882.606 (3)147
O1—H1···S1i0.822.923.1746 (18)100
C12—H12···O1i0.932.593.328 (3)136
C12—H12···O2i0.932.603.491 (3)160

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2526).

References

  • Garnovski, A. D., Nivorozhkin, A. L. & Minki, V. I. (1993). Coord. Chem. Rev.126, 1–69.
  • 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.
  • Zhao, R.-G., Lu, J. & Li, J.-K. (2008). Acta Cryst. E64, o499. [PMC free article] [PubMed]

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