Acta Cryst. (2009). E65, o2179 [ doi:10.1107/S160053680903205X ]
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.
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.
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).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
| C14H13NOS3 | F(000) = 640 |
| Mr = 307.43 | Dx = 1.473 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
| a = 11.9763 (13) Å | θ = 9–12° |
| b = 8.2333 (13) Å | µ = 0.52 mm−1 |
| c = 14.2213 (13) Å | T = 296 K |
| β = 98.723 (3)° | Block, yellow |
| V = 1386.1 (3) Å3 | 0.28 × 0.25 × 0.25 mm |
| Z = 4 |
| Enraf–Nonius CAD-4 diffractometer | 2443 independent reflections |
| Radiation source: fine-focus sealed tube | 1929 reflections with I > 2σ(I) |
| graphite | Rint = 0.025 |
| ω/2θ scans | θmax = 25.0°, θmin = 1.7° |
| Absorption correction: ψ scan (North et al., 1968) | h = −14→10 |
| Tmin = 0.867, Tmax = 0.880 | k = −9→9 |
| 7137 measured reflections | l = −16→16 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.140 | H-atom parameters constrained |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.0746P)2 + 0.5508P] where P = (Fo2 + 2Fc2)/3 |
| 2443 reflections | (Δ/σ)max = 0.002 |
| 176 parameters | Δρmax = 0.28 e Å−3 |
| 0 restraints | Δρmin = −0.39 e Å−3 |
| C14H13NOS3 | V = 1386.1 (3) Å3 |
| Mr = 307.43 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 11.9763 (13) Å | µ = 0.52 mm−1 |
| b = 8.2333 (13) Å | T = 296 K |
| c = 14.2213 (13) Å | 0.28 × 0.25 × 0.25 mm |
| β = 98.723 (3)° |
| Enraf–Nonius CAD-4 diffractometer | 1929 reflections with I > 2σ(I) |
| Absorption correction: ψ scan (North et al., 1968) | Rint = 0.025 |
| Tmin = 0.867, Tmax = 0.880 | θmax = 25.0° |
| 7137 measured reflections | Standard reflections: 0 |
| 2443 independent reflections |
| R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
| wR(F2) = 0.140 | Δρmax = 0.28 e Å−3 |
| S = 1.06 | Δρmin = −0.39 e Å−3 |
| 2443 reflections | Absolute structure: ? |
| 176 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | ||
| C2 | 0.3001 (2) | 0.0386 (3) | −0.0207 (2) | 0.0502 (6) | |
| H2 | 0.2415 | −0.0310 | −0.0118 | 0.060* | |
| C3 | 0.3723 (2) | 0.0988 (3) | 0.05602 (18) | 0.0468 (6) | |
| C4 | 0.46151 (19) | 0.2023 (3) | 0.04542 (18) | 0.0441 (6) | |
| C5 | 0.4777 (2) | 0.2435 (3) | −0.04744 (18) | 0.0448 (6) | |
| C6 | 0.4044 (2) | 0.1839 (3) | −0.1250 (2) | 0.0532 (7) | |
| H6 | 0.4148 | 0.2118 | −0.1864 | 0.064* | |
| C7 | 0.3166 (2) | 0.0837 (3) | −0.1110 (2) | 0.0538 (7) | |
| C8 | 0.9011 (2) | 0.3750 (3) | 0.1048 (2) | 0.0551 (7) | |
| C9 | 0.8496 (2) | 0.3907 (3) | 0.0113 (2) | 0.0478 (6) | |
| C10 | 0.7427 (2) | 0.4868 (3) | −0.0169 (3) | 0.0605 (8) | |
| H10A | 0.7476 | 0.5890 | 0.0174 | 0.073* | |
| H10B | 0.7333 | 0.5106 | −0.0844 | 0.073* | |
| C11 | 0.8989 (2) | 0.3091 (3) | −0.0574 (2) | 0.0594 (7) | |
| H11 | 0.8660 | 0.3151 | −0.1209 | 0.071* | |
| C12 | 0.9966 (3) | 0.2189 (4) | −0.0324 (3) | 0.0718 (9) | |
| H12 | 1.0297 | 0.1668 | −0.0792 | 0.086* | |
| C13 | 1.0442 (3) | 0.2064 (4) | 0.0608 (3) | 0.0726 (9) | |
| H13 | 1.1092 | 0.1445 | 0.0772 | 0.087* | |
| C14 | 0.9971 (3) | 0.2840 (4) | 0.1300 (2) | 0.0690 (8) | |
| H14 | 1.0297 | 0.2753 | 0.1934 | 0.083* | |
| C15 | 0.5736 (2) | 0.3436 (3) | −0.0638 (2) | 0.0523 (7) | |
| H15 | 0.5821 | 0.3710 | −0.1257 | 0.063* | |
| N1 | 0.64557 (17) | 0.3939 (3) | 0.00480 (18) | 0.0541 (6) | |
| O1 | 0.52860 (16) | 0.2588 (2) | 0.12252 (13) | 0.0597 (5) | |
| H1 | 0.5820 | 0.3078 | 0.1060 | 0.090* | |
| S1 | 0.35256 (7) | 0.04078 (11) | 0.16895 (5) | 0.0677 (3) | |
| H1A | 0.4408 | −0.0037 | 0.2128 | 0.102* | |
| S2 | 0.22437 (8) | 0.01029 (13) | −0.20692 (7) | 0.0860 (4) | |
| H2A | 0.2734 | −0.0823 | −0.2515 | 0.129* | |
| S3 | 0.84366 (10) | 0.47293 (14) | 0.19417 (7) | 0.0939 (4) | |
| H3A | 0.8005 | 0.5977 | 0.1640 | 0.141* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C2 | 0.0407 (14) | 0.0441 (14) | 0.0657 (18) | 0.0040 (11) | 0.0080 (12) | −0.0050 (12) |
| C3 | 0.0450 (14) | 0.0445 (14) | 0.0537 (15) | 0.0098 (11) | 0.0161 (11) | −0.0037 (11) |
| C4 | 0.0379 (13) | 0.0410 (13) | 0.0531 (15) | 0.0074 (10) | 0.0060 (11) | −0.0070 (11) |
| C5 | 0.0394 (13) | 0.0392 (13) | 0.0555 (15) | 0.0099 (10) | 0.0059 (11) | 0.0044 (11) |
| C6 | 0.0543 (16) | 0.0523 (15) | 0.0514 (15) | 0.0073 (12) | 0.0029 (12) | 0.0093 (12) |
| C7 | 0.0475 (15) | 0.0527 (15) | 0.0575 (17) | 0.0041 (12) | −0.0037 (12) | −0.0010 (13) |
| C8 | 0.0483 (15) | 0.0544 (16) | 0.0643 (18) | −0.0054 (13) | 0.0144 (13) | −0.0064 (13) |
| C9 | 0.0399 (13) | 0.0369 (13) | 0.0683 (17) | −0.0032 (10) | 0.0136 (12) | 0.0039 (11) |
| C10 | 0.0440 (15) | 0.0444 (15) | 0.095 (2) | 0.0030 (11) | 0.0151 (14) | 0.0117 (14) |
| C11 | 0.0616 (17) | 0.0542 (16) | 0.0662 (18) | 0.0002 (13) | 0.0223 (14) | 0.0053 (13) |
| C12 | 0.072 (2) | 0.0588 (18) | 0.094 (2) | 0.0109 (15) | 0.0409 (19) | −0.0026 (17) |
| C13 | 0.0478 (17) | 0.067 (2) | 0.105 (3) | 0.0124 (15) | 0.0171 (17) | 0.0114 (19) |
| C14 | 0.0527 (17) | 0.076 (2) | 0.075 (2) | −0.0016 (15) | −0.0010 (15) | 0.0072 (17) |
| C15 | 0.0477 (15) | 0.0453 (14) | 0.0651 (17) | 0.0099 (12) | 0.0121 (13) | 0.0103 (12) |
| N1 | 0.0395 (12) | 0.0460 (12) | 0.0771 (16) | 0.0029 (9) | 0.0100 (11) | 0.0029 (11) |
| O1 | 0.0542 (11) | 0.0678 (13) | 0.0566 (11) | −0.0068 (9) | 0.0063 (9) | −0.0133 (9) |
| S1 | 0.0733 (5) | 0.0826 (6) | 0.0530 (5) | −0.0086 (4) | 0.0280 (4) | −0.0057 (4) |
| S2 | 0.0784 (6) | 0.1025 (7) | 0.0678 (6) | −0.0198 (5) | −0.0192 (4) | −0.0078 (5) |
| S3 | 0.1002 (8) | 0.1088 (8) | 0.0779 (6) | 0.0057 (6) | 0.0300 (5) | −0.0335 (5) |
| C2—C3 | 1.377 (4) | C10—N1 | 1.464 (3) |
| C2—C7 | 1.380 (4) | C10—H10A | 0.9700 |
| C2—H2 | 0.9300 | C10—H10B | 0.9700 |
| C3—C4 | 1.392 (4) | C11—C12 | 1.386 (4) |
| C3—S1 | 1.726 (3) | C11—H11 | 0.9300 |
| C4—O1 | 1.341 (3) | C12—C13 | 1.364 (5) |
| C4—C5 | 1.405 (4) | C12—H12 | 0.9300 |
| C5—C6 | 1.391 (4) | C13—C14 | 1.365 (5) |
| C5—C15 | 1.461 (4) | C13—H13 | 0.9300 |
| C6—C7 | 1.374 (4) | C14—H14 | 0.9300 |
| C6—H6 | 0.9300 | C15—N1 | 1.269 (3) |
| C7—S2 | 1.729 (3) | C15—H15 | 0.9300 |
| C8—C14 | 1.374 (4) | O1—H1 | 0.8200 |
| C8—C9 | 1.384 (4) | S1—H1A | 1.2000 |
| C8—S3 | 1.733 (3) | S2—H2A | 1.2000 |
| C9—C11 | 1.390 (4) | S3—H3A | 1.2000 |
| C9—C10 | 1.507 (4) | ||
| C3—C2—C7 | 118.7 (2) | N1—C10—H10A | 109.7 |
| C3—C2—H2 | 120.7 | C9—C10—H10A | 109.7 |
| C7—C2—H2 | 120.7 | N1—C10—H10B | 109.7 |
| C2—C3—C4 | 122.3 (2) | C9—C10—H10B | 109.7 |
| C2—C3—S1 | 118.6 (2) | H10A—C10—H10B | 108.2 |
| C4—C3—S1 | 119.1 (2) | C12—C11—C9 | 120.7 (3) |
| O1—C4—C3 | 119.9 (2) | C12—C11—H11 | 119.7 |
| O1—C4—C5 | 122.3 (2) | C9—C11—H11 | 119.7 |
| C3—C4—C5 | 117.9 (2) | C13—C12—C11 | 120.1 (3) |
| C6—C5—C4 | 119.9 (2) | C13—C12—H12 | 119.9 |
| C6—C5—C15 | 119.4 (2) | C11—C12—H12 | 119.9 |
| C4—C5—C15 | 120.7 (2) | C12—C13—C14 | 120.5 (3) |
| C7—C6—C5 | 120.2 (3) | C12—C13—H13 | 119.7 |
| C7—C6—H6 | 119.9 | C14—C13—H13 | 119.7 |
| C5—C6—H6 | 119.9 | C13—C14—C8 | 119.3 (3) |
| C6—C7—C2 | 121.1 (2) | C13—C14—H14 | 120.4 |
| C6—C7—S2 | 120.5 (2) | C8—C14—H14 | 120.4 |
| C2—C7—S2 | 118.4 (2) | N1—C15—C5 | 121.4 (3) |
| C14—C8—C9 | 122.3 (3) | N1—C15—H15 | 119.3 |
| C14—C8—S3 | 118.2 (2) | C5—C15—H15 | 119.3 |
| C9—C8—S3 | 119.5 (2) | C15—N1—C10 | 118.5 (3) |
| C8—C9—C11 | 117.1 (2) | C4—O1—H1 | 109.5 |
| C8—C9—C10 | 122.8 (3) | C3—S1—H1A | 109.5 |
| C11—C9—C10 | 120.0 (3) | C7—S2—H2A | 109.5 |
| N1—C10—C9 | 109.9 (2) | C8—S3—H3A | 109.5 |
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.
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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.
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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.
![[Figure 1]](./hb5045fig1thm.gif)
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) °.