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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2204.
Published online 2009 August 22. doi:  10.1107/S1600536809032401
PMCID: PMC2969939

2-(2-Furylmethyl­amino­meth­yl)-4-sulfanylphenol

Abstract

In the title compound, C12H13NO2S, the dihedral angle between the furan and benzene rings is 62.2 (2)° and an intra­molecular O—H(...)N hydrogen bond is formed. In the crystal, mol­ecules are linked by weak inter­molecular N—H(...)S hydrogen bonds.

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-o2204-scheme1.jpg

Experimental

Crystal data

  • C12H13NO2S
  • M r = 235.29
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2204-efi1.jpg
  • a = 5.5778 (12) Å
  • b = 13.589 (3) Å
  • c = 14.943 (3) Å
  • V = 1132.6 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 293 K
  • 0.30 × 0.30 × 0.10 mm

Data collection

  • Enraf–Nonius CAD4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.924, T max = 0.974
  • 2528 measured reflections
  • 2216 independent reflections
  • 1811 reflections with I > 2σ(I)
  • R int = 0.034
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.166
  • S = 1.06
  • 2216 reflections
  • 150 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.46 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 900 Friedel pairs
  • Flack parameter: 0.00 (17)

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/S1600536809032401/hb5047sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032401/hb5047Isup2.hkl

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

Acknowledgments

The project was supported by the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry, Educational Commission of Hubei Province (D20091703) and the Natural Science Foundation of Hubei Province (2008CDB038).

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 are an intramolecular O-H···N hydrogen bond and an intermolecular N-H···S hydrogen bond in (I).

Experimental

A mixture of 2-hydroxy-5-mercaptobenzaldehyde (154 mg, 1 mmol) and furan-2-ylmethanamine (97 mg, 1 mmol) were stirred in methanol (10 ml) for 2 h. Then NaBH4 (76 mg, 2 mmol) was added to the reaction solution slowly, and stirred at room temperature for 2 h. The mixture was evaporated under vacuum, and dissolved in dichloromethane (5 ml). The solution was washed with saturated NaCl solution and water, respectively, dried over anhydrous sodium sulfate, and evaporated. Purification by silica gel afforded pure product. Colourless blocks of (I) were obtained by recrystallization of the pure product in methanol.

Refinement

The N-bound H atom was located in a difference map and its position was freely refined. The other H atoms were positioned geometrically (C—H = 0.93–0.97Å, O—H = 0.82Å, 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

C12H13NO2SF(000) = 496
Mr = 235.29Dx = 1.380 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 5.5778 (12) Åθ = 9–12°
b = 13.589 (3) ŵ = 0.27 mm1
c = 14.943 (3) ÅT = 293 K
V = 1132.6 (4) Å3Block, colorless
Z = 40.30 × 0.30 × 0.10 mm

Data collection

Enraf–Nonius CAD4 diffractometer1811 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
graphiteθmax = 26.0°, θmin = 2.0°
ω/2θ scansh = −6→0
Absorption correction: ψ scan (North et al., 1968)k = −16→16
Tmin = 0.924, Tmax = 0.974l = −18→0
2528 measured reflections3 standard reflections every 200 reflections
2216 independent reflections intensity decay: 1%

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.058w = 1/[σ2(Fo2) + (0.1031P)2 + 0.1612P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.166(Δ/σ)max = 0.002
S = 1.06Δρmax = 0.35 e Å3
2216 reflectionsΔρmin = −0.46 e Å3
150 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.058 (9)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 900 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.00 (17)

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
C1−0.2480 (7)0.7259 (3)0.4206 (3)0.0591 (10)
H1−0.39480.72880.45010.071*
C2−0.1233 (8)0.6441 (3)0.4068 (3)0.0581 (9)
H2−0.16590.58070.42390.070*
C30.0881 (8)0.6728 (3)0.3607 (3)0.0564 (10)
H30.21080.63120.34200.068*
C40.0791 (6)0.7696 (3)0.3490 (2)0.0480 (8)
C50.2431 (8)0.8424 (3)0.3079 (3)0.0600 (10)
H5A0.27950.89330.35120.072*
H5B0.39230.81000.29200.072*
C60.1385 (8)0.8197 (2)0.1507 (2)0.0526 (9)
H6A0.05510.75970.16710.063*
H6B0.30230.80250.13540.063*
C70.0183 (6)0.8652 (2)0.0710 (2)0.0422 (8)
C80.1130 (6)0.8552 (2)−0.0141 (2)0.0449 (8)
H80.25580.8209−0.02190.054*
C9−0.0009 (7)0.8953 (3)−0.0874 (3)0.0481 (8)
C10−0.2099 (8)0.9468 (3)−0.0782 (3)0.0591 (10)
H10−0.28560.9737−0.12800.071*
C11−0.3069 (7)0.9583 (3)0.0062 (3)0.0613 (11)
H11−0.44800.99390.01340.074*
C12−0.1958 (6)0.9172 (3)0.0804 (3)0.0502 (9)
H1C0.230 (9)0.942 (3)0.212 (3)0.060*
N10.1391 (7)0.8878 (2)0.2275 (2)0.0550 (8)
O1−0.1310 (6)0.8050 (2)0.38570 (18)0.0632 (8)
O2−0.2984 (5)0.9310 (2)0.1623 (2)0.0696 (8)
H2A−0.21700.90380.20070.104*
S10.1282 (2)0.88051 (8)−0.19340 (6)0.0635 (4)
H1A0.34230.8770−0.18630.095*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.041 (2)0.091 (3)0.0460 (19)0.001 (2)0.0025 (17)0.011 (2)
C20.052 (2)0.063 (2)0.059 (2)−0.006 (2)0.005 (2)0.0063 (17)
C30.053 (2)0.058 (2)0.057 (2)0.0042 (18)0.010 (2)−0.0024 (18)
C40.0402 (19)0.062 (2)0.0419 (17)0.0025 (16)−0.0010 (15)−0.0007 (16)
C50.058 (2)0.068 (2)0.054 (2)−0.015 (2)−0.007 (2)0.0067 (19)
C60.055 (2)0.0490 (18)0.054 (2)0.0003 (19)0.002 (2)0.0033 (16)
C70.0361 (17)0.0396 (16)0.0508 (19)−0.0041 (15)−0.0016 (15)−0.0001 (14)
C80.0382 (17)0.0426 (16)0.0540 (19)0.0009 (15)0.0022 (17)−0.0009 (14)
C90.047 (2)0.0470 (18)0.0501 (19)−0.0058 (17)−0.0034 (17)0.0017 (15)
C100.054 (2)0.057 (2)0.066 (2)0.0046 (19)−0.017 (2)0.0031 (19)
C110.041 (2)0.060 (2)0.083 (3)0.0110 (17)−0.007 (2)−0.002 (2)
C120.0385 (19)0.0486 (18)0.064 (2)−0.0037 (15)0.0074 (17)−0.0040 (17)
N10.064 (2)0.0487 (16)0.0518 (16)−0.0126 (18)−0.0062 (16)0.0024 (14)
O10.0598 (17)0.0678 (16)0.0619 (16)0.0180 (15)0.0025 (15)0.0038 (12)
O20.0543 (17)0.0815 (18)0.0731 (19)0.0024 (15)0.0224 (15)−0.0063 (15)
S10.0710 (7)0.0711 (7)0.0486 (5)−0.0030 (6)0.0064 (5)0.0029 (4)

Geometric parameters (Å, °)

C1—C21.328 (6)C6—H6B0.9700
C1—O11.361 (5)C7—C81.383 (5)
C1—H10.9300C7—C121.394 (5)
C2—C31.420 (6)C8—C91.379 (5)
C2—H20.9300C8—H80.9300
C3—C41.327 (5)C9—C101.366 (6)
C3—H30.9300C9—S11.752 (4)
C4—O11.381 (5)C10—C111.382 (6)
C4—C51.481 (5)C10—H100.9300
C5—N11.470 (5)C11—C121.388 (6)
C5—H5A0.9700C11—H110.9300
C5—H5B0.9700C12—O21.365 (5)
C6—N11.473 (5)N1—H1C0.93 (5)
C6—C71.501 (5)O2—H2A0.8200
C6—H6A0.9700S1—H1A1.2000
C2—C1—O1110.5 (3)C8—C7—C12118.0 (3)
C2—C1—H1124.8C8—C7—C6121.2 (3)
O1—C1—H1124.8C12—C7—C6120.7 (3)
C1—C2—C3106.3 (4)C9—C8—C7121.0 (3)
C1—C2—H2126.8C9—C8—H8119.5
C3—C2—H2126.8C7—C8—H8119.5
C4—C3—C2107.7 (4)C10—C9—C8121.1 (4)
C4—C3—H3126.1C10—C9—S1120.0 (3)
C2—C3—H3126.1C8—C9—S1118.9 (3)
C3—C4—O1108.9 (3)C9—C10—C11118.9 (4)
C3—C4—C5133.9 (4)C9—C10—H10120.6
O1—C4—C5117.2 (3)C11—C10—H10120.6
N1—C5—C4112.1 (3)C10—C11—C12120.6 (4)
N1—C5—H5A109.2C10—C11—H11119.7
C4—C5—H5A109.2C12—C11—H11119.7
N1—C5—H5B109.2O2—C12—C11118.3 (3)
C4—C5—H5B109.2O2—C12—C7121.3 (4)
H5A—C5—H5B107.9C11—C12—C7120.4 (4)
N1—C6—C7111.1 (3)C5—N1—C6111.9 (3)
N1—C6—H6A109.4C5—N1—H1C109 (3)
C7—C6—H6A109.4C6—N1—H1C108 (2)
N1—C6—H6B109.4C1—O1—C4106.5 (3)
C7—C6—H6B109.4C12—O2—H2A109.5
H6A—C6—H6B108.0C9—S1—H1A109.5
O1—C1—C2—C30.5 (5)S1—C9—C10—C11−179.4 (3)
C1—C2—C3—C4−0.2 (5)C9—C10—C11—C12−0.8 (6)
C2—C3—C4—O1−0.1 (4)C10—C11—C12—O2179.7 (4)
C2—C3—C4—C5178.8 (4)C10—C11—C12—C71.3 (6)
C3—C4—C5—N1114.6 (5)C8—C7—C12—O2−179.2 (3)
O1—C4—C5—N1−66.5 (4)C6—C7—C12—O22.2 (5)
N1—C6—C7—C8137.6 (3)C8—C7—C12—C11−0.8 (5)
N1—C6—C7—C12−43.8 (5)C6—C7—C12—C11−179.4 (3)
C12—C7—C8—C9−0.1 (5)C4—C5—N1—C6−73.9 (4)
C6—C7—C8—C9178.6 (3)C7—C6—N1—C5176.6 (3)
C7—C8—C9—C100.5 (5)C2—C1—O1—C4−0.6 (4)
C7—C8—C9—S1179.8 (3)C3—C4—O1—C10.4 (4)
C8—C9—C10—C110.0 (6)C5—C4—O1—C1−178.7 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2A···N10.822.042.692 (5)136
N1—H1C···S1i0.93 (5)2.90 (4)3.605 (3)134 (3)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5047).

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.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • 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