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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2179.
Published online 2009 August 19. doi:  10.1107/S160053680903205X
PMCID: PMC2969949

2,4-Disulfanyl-6-[(E)-(2-sulfanylbenz­yl)imino­meth­yl]phenol

Abstract

In the title compound, C14H13NOS3, the dihedral angle between the benzene rings is 73.26 (5)° and an intra­molecular O—H(...)N hydrogen bond occurs.

Related literature

For background, see: Shi et al. (2007 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]);

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Object name is e-65-o2179-scheme1.jpg

Experimental

Crystal data

  • C14H13NOS3
  • M r = 307.43
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2179-efi1.jpg
  • a = 11.9763 (13) Å
  • b = 8.2333 (13) Å
  • c = 14.2213 (13) Å
  • β = 98.723 (3)°
  • V = 1386.1 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.52 mm−1
  • T = 296 K
  • 0.28 × 0.25 × 0.25 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.867, T max = 0.880
  • 7137 measured reflections
  • 2443 independent reflections
  • 1929 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.140
  • S = 1.06
  • 2443 reflections
  • 176 parameters
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.39 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); 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/S160053680903205X/hb5045sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903205X/hb5045Isup2.hkl

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

supplementary crystallographic information

Comment

There has been much research interest in Schiff base compounds due to their biological activities (Shi et al., 2007). In this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). There ais an intramolecular O—H···N hydrogen bond (Table 1) in (I). The dihedral angle between the two benzene rings is 73.26 (0.05) °.

Experimental

A mixture of 2-hydroxy-3,5-disulfanylbenzaldehyde (186 mg, 1 mmol) and 2-(aminomethyl)benzenethiol (139 mg, 1 mmol) in methanol (10 ml) was stirred for 2 h. After keeping the filtrate in air for 6 d, yellow blocks of (I) were formed.

Refinement

All H atoms were positioned geometrically (C—H = 0.93–0.97 Å, S—H = 1.20Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl C).

Figures

Fig. 1.
The molecular structure of (I) showing 30% probability displacement ellipsoids.

Crystal data

C14H13NOS3F(000) = 640
Mr = 307.43Dx = 1.473 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 11.9763 (13) Åθ = 9–12°
b = 8.2333 (13) ŵ = 0.52 mm1
c = 14.2213 (13) ÅT = 296 K
β = 98.723 (3)°Block, yellow
V = 1386.1 (3) Å30.28 × 0.25 × 0.25 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer2443 independent reflections
Radiation source: fine-focus sealed tube1929 reflections with I > 2σ(I)
graphiteRint = 0.025
ω/2θ scansθmax = 25.0°, θmin = 1.7°
Absorption correction: ψ scan (North et al., 1968)h = −14→10
Tmin = 0.867, Tmax = 0.880k = −9→9
7137 measured reflectionsl = −16→16

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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0746P)2 + 0.5508P] where P = (Fo2 + 2Fc2)/3
2443 reflections(Δ/σ)max = 0.002
176 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = −0.39 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
C20.3001 (2)0.0386 (3)−0.0207 (2)0.0502 (6)
H20.2415−0.0310−0.01180.060*
C30.3723 (2)0.0988 (3)0.05602 (18)0.0468 (6)
C40.46151 (19)0.2023 (3)0.04542 (18)0.0441 (6)
C50.4777 (2)0.2435 (3)−0.04744 (18)0.0448 (6)
C60.4044 (2)0.1839 (3)−0.1250 (2)0.0532 (7)
H60.41480.2118−0.18640.064*
C70.3166 (2)0.0837 (3)−0.1110 (2)0.0538 (7)
C80.9011 (2)0.3750 (3)0.1048 (2)0.0551 (7)
C90.8496 (2)0.3907 (3)0.0113 (2)0.0478 (6)
C100.7427 (2)0.4868 (3)−0.0169 (3)0.0605 (8)
H10A0.74760.58900.01740.073*
H10B0.73330.5106−0.08440.073*
C110.8989 (2)0.3091 (3)−0.0574 (2)0.0594 (7)
H110.86600.3151−0.12090.071*
C120.9966 (3)0.2189 (4)−0.0324 (3)0.0718 (9)
H121.02970.1668−0.07920.086*
C131.0442 (3)0.2064 (4)0.0608 (3)0.0726 (9)
H131.10920.14450.07720.087*
C140.9971 (3)0.2840 (4)0.1300 (2)0.0690 (8)
H141.02970.27530.19340.083*
C150.5736 (2)0.3436 (3)−0.0638 (2)0.0523 (7)
H150.58210.3710−0.12570.063*
N10.64557 (17)0.3939 (3)0.00480 (18)0.0541 (6)
O10.52860 (16)0.2588 (2)0.12252 (13)0.0597 (5)
H10.58200.30780.10600.090*
S10.35256 (7)0.04078 (11)0.16895 (5)0.0677 (3)
H1A0.4408−0.00370.21280.102*
S20.22437 (8)0.01029 (13)−0.20692 (7)0.0860 (4)
H2A0.2734−0.0823−0.25150.129*
S30.84366 (10)0.47293 (14)0.19417 (7)0.0939 (4)
H3A0.80050.59770.16400.141*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C20.0407 (14)0.0441 (14)0.0657 (18)0.0040 (11)0.0080 (12)−0.0050 (12)
C30.0450 (14)0.0445 (14)0.0537 (15)0.0098 (11)0.0161 (11)−0.0037 (11)
C40.0379 (13)0.0410 (13)0.0531 (15)0.0074 (10)0.0060 (11)−0.0070 (11)
C50.0394 (13)0.0392 (13)0.0555 (15)0.0099 (10)0.0059 (11)0.0044 (11)
C60.0543 (16)0.0523 (15)0.0514 (15)0.0073 (12)0.0029 (12)0.0093 (12)
C70.0475 (15)0.0527 (15)0.0575 (17)0.0041 (12)−0.0037 (12)−0.0010 (13)
C80.0483 (15)0.0544 (16)0.0643 (18)−0.0054 (13)0.0144 (13)−0.0064 (13)
C90.0399 (13)0.0369 (13)0.0683 (17)−0.0032 (10)0.0136 (12)0.0039 (11)
C100.0440 (15)0.0444 (15)0.095 (2)0.0030 (11)0.0151 (14)0.0117 (14)
C110.0616 (17)0.0542 (16)0.0662 (18)0.0002 (13)0.0223 (14)0.0053 (13)
C120.072 (2)0.0588 (18)0.094 (2)0.0109 (15)0.0409 (19)−0.0026 (17)
C130.0478 (17)0.067 (2)0.105 (3)0.0124 (15)0.0171 (17)0.0114 (19)
C140.0527 (17)0.076 (2)0.075 (2)−0.0016 (15)−0.0010 (15)0.0072 (17)
C150.0477 (15)0.0453 (14)0.0651 (17)0.0099 (12)0.0121 (13)0.0103 (12)
N10.0395 (12)0.0460 (12)0.0771 (16)0.0029 (9)0.0100 (11)0.0029 (11)
O10.0542 (11)0.0678 (13)0.0566 (11)−0.0068 (9)0.0063 (9)−0.0133 (9)
S10.0733 (5)0.0826 (6)0.0530 (5)−0.0086 (4)0.0280 (4)−0.0057 (4)
S20.0784 (6)0.1025 (7)0.0678 (6)−0.0198 (5)−0.0192 (4)−0.0078 (5)
S30.1002 (8)0.1088 (8)0.0779 (6)0.0057 (6)0.0300 (5)−0.0335 (5)

Geometric parameters (Å, °)

C2—C31.377 (4)C10—N11.464 (3)
C2—C71.380 (4)C10—H10A0.9700
C2—H20.9300C10—H10B0.9700
C3—C41.392 (4)C11—C121.386 (4)
C3—S11.726 (3)C11—H110.9300
C4—O11.341 (3)C12—C131.364 (5)
C4—C51.405 (4)C12—H120.9300
C5—C61.391 (4)C13—C141.365 (5)
C5—C151.461 (4)C13—H130.9300
C6—C71.374 (4)C14—H140.9300
C6—H60.9300C15—N11.269 (3)
C7—S21.729 (3)C15—H150.9300
C8—C141.374 (4)O1—H10.8200
C8—C91.384 (4)S1—H1A1.2000
C8—S31.733 (3)S2—H2A1.2000
C9—C111.390 (4)S3—H3A1.2000
C9—C101.507 (4)
C3—C2—C7118.7 (2)N1—C10—H10A109.7
C3—C2—H2120.7C9—C10—H10A109.7
C7—C2—H2120.7N1—C10—H10B109.7
C2—C3—C4122.3 (2)C9—C10—H10B109.7
C2—C3—S1118.6 (2)H10A—C10—H10B108.2
C4—C3—S1119.1 (2)C12—C11—C9120.7 (3)
O1—C4—C3119.9 (2)C12—C11—H11119.7
O1—C4—C5122.3 (2)C9—C11—H11119.7
C3—C4—C5117.9 (2)C13—C12—C11120.1 (3)
C6—C5—C4119.9 (2)C13—C12—H12119.9
C6—C5—C15119.4 (2)C11—C12—H12119.9
C4—C5—C15120.7 (2)C12—C13—C14120.5 (3)
C7—C6—C5120.2 (3)C12—C13—H13119.7
C7—C6—H6119.9C14—C13—H13119.7
C5—C6—H6119.9C13—C14—C8119.3 (3)
C6—C7—C2121.1 (2)C13—C14—H14120.4
C6—C7—S2120.5 (2)C8—C14—H14120.4
C2—C7—S2118.4 (2)N1—C15—C5121.4 (3)
C14—C8—C9122.3 (3)N1—C15—H15119.3
C14—C8—S3118.2 (2)C5—C15—H15119.3
C9—C8—S3119.5 (2)C15—N1—C10118.5 (3)
C8—C9—C11117.1 (2)C4—O1—H1109.5
C8—C9—C10122.8 (3)C3—S1—H1A109.5
C11—C9—C10120.0 (3)C7—S2—H2A109.5
N1—C10—C9109.9 (2)C8—S3—H3A109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.872.591 (3)147

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5045).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Enraf–Nonius (1989). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shi, L., Ge, H.-M., Tan, S.-H., Li, H.-Q., Song, Y.-C., Zhu, H.-L. & Tan, R.-X. (2007). Eur. J. Med. Chem.42, 558–564. [PubMed]

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