organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

5-Phenyl-1,2,5-di­thia­zepane

aDepartment of Chemistry, The University of Texas at Austin, 105 E 24th Street, Stop A5300, Austin, Texas 78712, USA
*Correspondence e-mail: bholliday@cm.utexas.edu

(Received 23 September 2013; accepted 29 January 2014; online 12 February 2014)

In the title compound, C10H13NS2, the seven-membered ring adopts a chair conformation. The S—S bond length is 2.0406 (5) Å and the C—S—S—C torsion angle is −83.89 (7)°. The amine group is sp2-hybridized. In the crystal, mol­ecules are linked into chains along [001] by weak inter­molecular S⋯S contacts of 3.5246 (5) Å.

Related literature

For properties of di­sulfide compounds, see: Pazderlová et al. (2012[Pazderlová, M., Bednárová, L., Dlouhá, H., Flegel, M., Lebl, M., Hlaváček, J., Setnička, V., Urbanová, M., Hynie, S., Klenerová, V., Baumruk, V. & Maloň, P. (2012). Biopolymers, 97, 923-932.]). For similar compounds, see: Roze et al. (2006[Roze, M., Kirichenko, N. & Neilands, O. (2006). Latv. Kim. Z. 4, 351-355.]); Bulavin (1971[Bulavin, L. G. (1971). Zh. Org. Khim. 7, 2604-2610.]). For related structures, see: Pickardt et al. (2006[Pickardt, J., von Chrzanowski, L. & Borowski, M. (2006). Acta Cryst. E62, o3401-o3402.]); Capasso et al. (1977[Capasso, S., Mattia, C., Mazzarella, L. & Puliti, R. (1977). Acta Cryst. B33, 2080-2083.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O. & Watson, D. G. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For previous reports of S⋯S inter­actions, see: Chen et al. (2009[Chen, H.-F., Fang, Q., Yu, W.-T., Batsanov, A. S. & Howard, J. A. K. (2009). Acta Cryst. C65, o198-o201.]); Reinheimer et al. (2009[Reinheimer, E. W., Fourmigué, M. & Dunbar, K. R. (2009). J. Chem. Crystallogr. 39, 723-729.]). For the calculation of the functionality of the amine group in terms of hybridization, see: Allen et al. (1995[Allen, F. H., Bird, C. M., Rowland, R. S., Harris, S. E. & Schwalbe, C. H. (1995). Acta Cryst. B51, 1068-1081.]). For the synthesis, see: Elderfield et al. (1958[Elderfield, R. C., Covey, I. S., Geiduschek, J. B., Meyer, W. L., Ross, A. B. & Ross, J. H. (1958). J. Org. Chem. 23, 1749-1753.]).

[Scheme 1]

Experimental

Crystal data
  • C10H13NS2

  • Mr = 211.33

  • Monoclinic, P 21 /c

  • a = 9.5760 (2) Å

  • b = 12.2310 (3) Å

  • c = 9.9811 (2) Å

  • β = 120.392 (2)°

  • V = 1008.38 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.48 mm−1

  • T = 153 K

  • 0.50 × 0.30 × 0.20 mm

Data collection
  • Nonius Kappa CCD diffractometer

  • Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.856, Tmax = 1

  • 3055 measured reflections

  • 1763 independent reflections

  • 1675 reflections with I > 2σ(I)

  • Rint = 0.012

Refinement
  • R[F2 > 2σ(F2)] = 0.024

  • wR(F2) = 0.064

  • S = 1.03

  • 1763 reflections

  • 118 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.21 e Å−3

Data collection: COLLECT (Nonius, 1998[Nonius (1998). KappaCCD Software. Nonius BV, Delft, The Netherlands.]); cell refinement: COLLECT; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]) within WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Cyclic disulfides are of special interest because they are often a key component in many biologically relevant peptides (Pazderlová et al., 2012). Because of this disulfide compounds are regularly found to have pharmacological activities. Herein is described the crystallographic properties of a 7-membered cyclic disulfide compound. The molecular structure of the title compound can be seen in Fig. 1.

The S—S bond distance is 2.0406 (5) Å. This value is comparable to other disulfide compounds. The mean average bond length for C—S—S—C bonds from 99 samples, reported by (Allen et al., 1987) is 2.048 Å. The torsion in the C—S—S—C bonds is -83.89 (7)°, this compares similarly to the C—S—S—C torsion in the 7-membered ring disulfide 1,2,4,6-tetrathiacycloheptane reported in (Pickardt et al., 2006), which has a C—S—S—C torsion of -89.4 (2)°.

The seven-membered ring adopts a chair conformation, as it does in the cyclic disulfide compound reported by Pickardt et al. (2006). The dominant intermolecular interactions are between S1···S2 of symmetry-related molecules. The contacts have a distance of 3.5246 (5) Å, this compares similarly to S···S interactions observed perviously by Chen et al. (2009) and Reinheimer et al. (2009) which are 3.396 (1) - 3.470 (1) Å and 3.580 (4) Å respectively.

The pyramidality of the amine functionality, measured by χn, the angle between the C1—N1 vector and the N1/C7/C9 plane, described by Allen et al. (1995), is 7.26 (15)°, indicating that the hybridization of the nitrogen atoms is mainly sp2 (sp2 χn 0°, sp3 χn 60°).

Related literature top

For properties of disulfide compounds, see: Pazderlová et al. (2012). For similar compounds, see: Roze et al. (2006); Bulavin (1971). For related structures, see: Pickardt et al. (2006); Capasso et al. (1977). For standard bond lengths, see: Allen et al. (1987). For previous reports of S···S interactions, see: Chen et al. (2009); Reinheimer et al. (2009). For the calculation of the functionality of the amine group in terms of hybridization, see: Allen et al. (1995). For the synthesis, see: Elderfield et al. (1958).

Experimental top

The title compound was prepared from N,N-bis(2-chloroethyl)aniline which had been prepared following literature methods reported by Elderfield et al. (1958). NaSH·H2O (1.08 g, 14.78 mmol) was stirred in ethanol (20 ml) under an argon atmosphere for 1 hr. N,N-bis(2-chloroethyl)aniline (0.5124 g, 2.35 mmol) was dissolved in ethanol (10 ml) under argon and then transferred into the NaSH·H2O solution via cannula. The reaction mixture was then heated to reflux for 24 hrs. The solvent volume was reduced by half in vacuo before degassed CH2Cl2 and H2O were added to the reaction flask and the product was extracted under argon. The organic phase was then transferred via cannula into a flask containing MgSO4. The product was isolated by filtration and removal of the solvent under vacuum. The X-ray quality crystals were obtained from a saturated dichloromethane solution of the title compound upon standing at 263 K for several days. Yield = 83%. 1H NMR (300 MHz, CDCl3): δ 7.25 (m, 2H), 6.85 (m, 3H), 3.52 (m, 4H), 2.74 (m, 4H).

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 Å and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: COLLECT (Nonius, 1998); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999) within WinGX (Farrugia, 2012); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure of title compound. Ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Part of the crystal structure viewed along the a axis. Interactions are shown between S1 and S2 of molecules related by the crystallographic c-glide.
5-Phenyl-1,2,5-dithiazepane top
Crystal data top
C10H13NS2F(000) = 448
Mr = 211.33Dx = 1.392 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybcCell parameters from 1974 reflections
a = 9.5760 (2) Åθ = 1.0–27.5°
b = 12.2310 (3) ŵ = 0.48 mm1
c = 9.9811 (2) ÅT = 153 K
β = 120.392 (2)°Block, white
V = 1008.38 (4) Å30.50 × 0.30 × 0.20 mm
Z = 4
Data collection top
Nonius Kappa CCD
diffractometer
1763 independent reflections
Radiation source: fine-focus sealed tube1675 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.012
ω scansθmax = 25.0°, θmin = 4.1°
Absorption correction: multi-scan
(DENZO and SCALEPACK; Otwinowski & Minor, 1997)
h = 1111
Tmin = 0.856, Tmax = 1k = 1214
3055 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0266P)2 + 0.5691P]
where P = (Fo2 + 2Fc2)/3
1763 reflections(Δ/σ)max = 0.002
118 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C10H13NS2V = 1008.38 (4) Å3
Mr = 211.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.5760 (2) ŵ = 0.48 mm1
b = 12.2310 (3) ÅT = 153 K
c = 9.9811 (2) Å0.50 × 0.30 × 0.20 mm
β = 120.392 (2)°
Data collection top
Nonius Kappa CCD
diffractometer
1763 independent reflections
Absorption correction: multi-scan
(DENZO and SCALEPACK; Otwinowski & Minor, 1997)
1675 reflections with I > 2σ(I)
Tmin = 0.856, Tmax = 1Rint = 0.012
3055 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0240 restraints
wR(F2) = 0.064H-atom parameters constrained
S = 1.03Δρmax = 0.25 e Å3
1763 reflectionsΔρmin = 0.21 e Å3
118 parameters
Special details top

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 > 2Σ(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) top
xyzUiso*/Ueq
S11.04272 (4)0.28440 (3)0.62971 (4)0.02268 (12)
S21.07376 (4)0.34787 (3)0.83210 (4)0.02409 (12)
N10.74239 (13)0.43703 (9)0.57782 (13)0.0190 (3)
C10.65295 (16)0.42454 (11)0.65031 (15)0.0187 (3)
C20.66903 (17)0.49796 (12)0.76593 (16)0.0218 (3)
H20.74340.55480.79650.026*
C30.57560 (17)0.48654 (13)0.83458 (16)0.0261 (3)
H30.58820.53600.91070.031*
C40.46349 (18)0.40283 (13)0.79229 (17)0.0282 (3)
H40.40060.39600.83860.034*
C50.44731 (17)0.32959 (13)0.67931 (17)0.0261 (3)
H50.37230.27320.64950.031*
C60.54029 (17)0.33875 (12)0.61020 (16)0.0223 (3)
H60.52850.28770.53620.027*
C70.72559 (17)0.36111 (11)0.45867 (16)0.0217 (3)
H7A0.75620.39820.39150.026*
H7B0.61250.34070.39580.026*
C80.82641 (17)0.25754 (11)0.52070 (17)0.0224 (3)
H8A0.80260.20960.43420.027*
H8B0.79560.21970.58730.027*
C90.87194 (17)0.51649 (11)0.63274 (17)0.0231 (3)
H9A0.82960.58680.64060.028*
H9B0.90370.52360.55500.028*
C101.02434 (18)0.49172 (12)0.78971 (17)0.0259 (3)
H10A1.01030.52290.87150.031*
H10B1.11570.52830.79260.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0207 (2)0.0222 (2)0.0268 (2)0.00209 (13)0.01317 (16)0.00058 (13)
S20.0215 (2)0.0287 (2)0.0192 (2)0.00065 (14)0.00822 (15)0.00285 (13)
N10.0195 (6)0.0174 (6)0.0198 (6)0.0004 (4)0.0097 (5)0.0012 (4)
C10.0171 (7)0.0180 (7)0.0177 (6)0.0048 (5)0.0062 (5)0.0045 (5)
C20.0202 (7)0.0199 (7)0.0222 (7)0.0019 (5)0.0085 (6)0.0003 (5)
C30.0253 (7)0.0307 (8)0.0217 (7)0.0072 (6)0.0115 (6)0.0004 (6)
C40.0225 (7)0.0376 (8)0.0274 (7)0.0064 (6)0.0148 (6)0.0083 (7)
C50.0178 (7)0.0270 (8)0.0296 (8)0.0004 (6)0.0090 (6)0.0063 (6)
C60.0196 (7)0.0209 (7)0.0219 (7)0.0010 (5)0.0072 (6)0.0000 (5)
C70.0223 (7)0.0235 (7)0.0180 (7)0.0018 (6)0.0091 (6)0.0007 (5)
C80.0215 (7)0.0206 (7)0.0242 (7)0.0005 (6)0.0109 (6)0.0044 (6)
C90.0280 (7)0.0183 (7)0.0275 (7)0.0024 (6)0.0173 (6)0.0002 (6)
C100.0241 (7)0.0238 (7)0.0291 (8)0.0048 (6)0.0130 (6)0.0069 (6)
Geometric parameters (Å, º) top
S1—C81.8171 (14)C5—C61.379 (2)
S1—S22.0406 (5)C5—H50.9300
S2—C101.8155 (15)C6—H60.9300
N1—C11.3811 (18)C7—C81.5216 (19)
N1—C71.4523 (18)C7—H7A0.9700
N1—C91.4478 (18)C7—H7B0.9700
C1—C21.408 (2)C8—H8A0.9700
C1—C61.410 (2)C8—H8B0.9700
C2—C31.382 (2)C9—C101.537 (2)
C2—H20.9300C9—H9A0.9700
C3—C41.386 (2)C9—H9B0.9700
C3—H30.9300C10—H10A0.9700
C4—C51.386 (2)C10—H10B0.9700
C4—H40.9300
C8—S1—S2102.27 (5)N1—C7—H7A108.6
C10—S2—S1104.34 (5)C8—C7—H7A108.6
C1—N1—C7121.14 (11)N1—C7—H7B108.6
C1—N1—C9121.04 (11)C8—C7—H7B108.6
C7—N1—C9117.26 (11)H7A—C7—H7B107.6
N1—C1—C2121.28 (12)C7—C8—S1112.92 (10)
N1—C1—C6121.45 (12)C7—C8—H8A109.0
C2—C1—C6117.26 (13)S1—C8—H8A109.0
C3—C2—C1120.81 (14)C7—C8—H8B109.0
C3—C2—H2119.6S1—C8—H8B109.0
C1—C2—H2119.6H8A—C8—H8B107.8
C2—C3—C4121.32 (14)N1—C9—C10116.32 (11)
C2—C3—H3119.3N1—C9—H9A108.2
C4—C3—H3119.3C10—C9—H9A108.2
C5—C4—C3118.41 (14)N1—C9—H9B108.2
C5—C4—H4120.8C10—C9—H9B108.2
C3—C4—H4120.8H9A—C9—H9B107.4
C6—C5—C4121.30 (14)C9—C10—S2115.45 (10)
C6—C5—H5119.3C9—C10—H10A108.4
C4—C5—H5119.3S2—C10—H10A108.4
C5—C6—C1120.88 (14)C9—C10—H10B108.4
C5—C6—H6119.6S2—C10—H10B108.4
C1—C6—H6119.6H10A—C10—H10B107.5
N1—C7—C8114.49 (11)
C8—S1—S2—C1083.89 (7)N1—C1—C6—C5177.53 (12)
C7—N1—C1—C2179.96 (12)C2—C1—C6—C51.6 (2)
C9—N1—C1—C28.78 (19)C1—N1—C7—C883.69 (15)
C7—N1—C1—C60.92 (19)C9—N1—C7—C887.82 (15)
C9—N1—C1—C6172.10 (12)N1—C7—C8—S162.44 (14)
N1—C1—C2—C3178.13 (12)S2—S1—C8—C773.74 (10)
C6—C1—C2—C31.0 (2)C1—N1—C9—C1069.91 (16)
C1—C2—C3—C40.0 (2)C7—N1—C9—C10101.60 (14)
C2—C3—C4—C50.4 (2)N1—C9—C10—S232.78 (16)
C3—C4—C5—C60.2 (2)S1—S2—C10—C944.11 (12)
C4—C5—C6—C11.3 (2)

Experimental details

Crystal data
Chemical formulaC10H13NS2
Mr211.33
Crystal system, space groupMonoclinic, P21/c
Temperature (K)153
a, b, c (Å)9.5760 (2), 12.2310 (3), 9.9811 (2)
β (°) 120.392 (2)
V3)1008.38 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.48
Crystal size (mm)0.50 × 0.30 × 0.20
Data collection
DiffractometerNonius Kappa CCD
diffractometer
Absorption correctionMulti-scan
(DENZO and SCALEPACK; Otwinowski & Minor, 1997)
Tmin, Tmax0.856, 1
No. of measured, independent and
observed [I > 2σ(I)] reflections
3055, 1763, 1675
Rint0.012
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.024, 0.064, 1.03
No. of reflections1763
No. of parameters118
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.21

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999) within WinGX (Farrugia, 2012), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

 

Acknowledgements

The Welch Foundation (grant No. F-1631) and the National Science Foundation (grant No. CHE-0847763) are acknowledged for financial support of this research.

References

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