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The title compound, C12H24N+·C6H5S, has been obtained by the reaction of C6H5SH with di­cyclo­hexyl­amine. The two ionic fragments are linked together in long chains by ...N—H...S... hydrogen bonds. There are two formula units in the asymmetric unit.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803009255/bt6273sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803009255/bt6273Isup2.hkl
Contains datablock I

CCDC reference: 214812

Key indicators

  • Single-crystal X-ray study
  • T = 200 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.039
  • wR factor = 0.144
  • Data-to-parameter ratio = 9.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
PLAT_353 Alert B Long N-H Bond (0.87A) N(2) - H(2A) = 1.12 Ang. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.42 From the CIF: _reflns_number_total 3593 Count of symmetry unique reflns 3711 Completeness (_total/calc) 96.82% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check

Comment top

The title compound, (I), was obtained previously in polycrystalline form (Dance, 1979). It was found to be a good isolatable source of the benzenethiolate anion for preparation of metal thiolates. On the other hand, there is a need for information in the study of N—H···S bonding. Such bonding plays a crucial role in biological systems, e.g. on the modification of redox potential in iron–sulfur proteins (Nakamura et al., 1988). Detailed research on N—H···S hydrogen bonding in simple molecules is therefore important.

The asymmetric unit of (I) consists of two benzenethiolate anions and two dicyclohexylammonium cations. The ions are linked in zigzag chains by S···H—N—H··· hydrogen bonding, motif C(4) (Etter, 1990). The donor–acceptor S···N distances [range 3.194 (5)–3.266 (5) Å] are comparable with the data observed in complex zinc and cobalt benzenethiolates [(C6H11)2NH2]2[Zn2(SC6H5)6] (Chung et al., 1991a), [(C6H11)2NH2]2[Co(SC6H5)4] (Chung et al., 1991b) and in [(CH3)3NCH2CONH2][SC6H5] (Walters et al., 1991).

Experimental top

All manipulations were carried out under argon by means of standard Schlenk techniques. The solvent and the amine were dried by standard methods and distilled under argon prior to use. To a solution of benzenethiol (0.22 g, 2 mmol) in acetonitrile, freshly prepared dicyclohexylamine (0.36 g, 2 mmol) was added. Immediately a white precipitate formed. Eecrystallization from hot acetonitrile afforded colourless crystals of (I) suitable for X-ray diffraction analysis.

Refinement top

H atoms bonded to C atoms were treated as riding, with fixed isotropic displacement parameters. The coordinates of the H atoms bonded to N atoms were refined.

Computing details top

Data collection: KM4 System (Gałdecki, Kowalski & Uszyński, 1996); cell refinement: KM4 System; data reduction: DATAPROC (Gałdecki, Kowalski, Kucharczyk & Uszyński, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: RESVIEW (Schwenk, 1998); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. All H atoms bonded to C atoms have been omitted.
[Figure 2] Fig. 2. Diagram of the hydrogen-bond network.
Dicyclohexylammonium benzenethiolate top
Crystal data top
C12H24N+·C6H5SDx = 1.119 Mg m3
Mr = 291.50Melting point = 99–100 K
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 40 reflections
a = 21.208 (4) Åθ = 2.8–18.7°
b = 11.678 (2) ŵ = 0.18 mm1
c = 13.974 (3) ÅT = 200 K
V = 3460.9 (12) Å3Plate, colourless
Z = 80.5 × 0.4 × 0.1 mm
F(000) = 1280
Data collection top
Oxford Diffraction KM-4
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 26.4°, θmin = 1.7°
Graphite monochromatorh = 260
w–2θ scansk = 140
3593 measured reflectionsl = 017
3593 independent reflections3 standard reflections every 200 reflections
2159 reflections with I > 2σ(I) intensity decay: 0.3%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.144 w = 1/[σ2(Fo2) + (0.079P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.032
3593 reflectionsΔρmax = 0.30 e Å3
373 parametersΔρmin = 0.26 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (13)
Crystal data top
C12H24N+·C6H5SV = 3460.9 (12) Å3
Mr = 291.50Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 21.208 (4) ŵ = 0.18 mm1
b = 11.678 (2) ÅT = 200 K
c = 13.974 (3) Å0.5 × 0.4 × 0.1 mm
Data collection top
Oxford Diffraction KM-4
diffractometer
Rint = 0.000
3593 measured reflections3 standard reflections every 200 reflections
3593 independent reflections intensity decay: 0.3%
2159 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.144Δρmax = 0.30 e Å3
S = 1.04Δρmin = 0.26 e Å3
3593 reflectionsAbsolute structure: Flack (1983)
373 parametersAbsolute structure parameter: 0.06 (13)
1 restraint
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 > 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) top
xyzUiso*/Ueq
S10.02122 (6)0.74871 (11)0.10577 (10)0.0338 (3)
S20.02996 (7)0.82635 (14)0.73194 (11)0.0500 (4)
N10.0231 (2)0.9837 (4)0.5563 (3)0.0270 (9)
H1A0.028 (2)1.060 (5)0.573 (4)0.032*
H1B0.000 (2)0.947 (4)0.604 (4)0.032*
N20.01441 (19)0.3655 (4)0.3983 (3)0.0296 (9)
H2A0.023 (2)0.291 (5)0.350 (4)0.035*
H2B0.016 (2)0.323 (5)0.450 (4)0.035*
C10.0546 (2)0.7407 (4)0.1570 (3)0.0317 (11)
C20.0904 (3)0.6414 (5)0.1502 (4)0.0427 (14)
H20.07270.57520.12120.051*
C30.1519 (3)0.6375 (5)0.1853 (5)0.0520 (16)
H30.17590.56920.17910.062*
C40.1777 (3)0.7308 (5)0.2286 (5)0.0495 (15)
H40.21960.72810.25230.059*
C50.1423 (2)0.8292 (5)0.2376 (4)0.0411 (13)
H50.16010.89450.26780.049*
C60.0812 (2)0.8339 (4)0.2033 (4)0.0341 (12)
H60.05720.90180.21150.041*
C70.0902 (2)0.9442 (4)0.5506 (4)0.0298 (11)
H70.09000.86020.53680.036*
C80.1208 (2)0.9619 (6)0.6454 (4)0.0409 (13)
H8A0.12001.04430.66180.049*
H8B0.09690.92000.69520.049*
C90.1888 (3)0.9197 (6)0.6441 (5)0.0528 (16)
H9A0.18910.83540.63630.063*
H9B0.20900.93800.70610.063*
C100.2259 (3)0.9732 (7)0.5648 (4)0.0607 (19)
H10A0.23171.05570.57850.073*
H10B0.26810.93720.56180.073*
C110.1932 (3)0.9596 (7)0.4686 (5)0.062 (2)
H11A0.19320.87780.45020.075*
H11B0.21691.00270.41930.075*
C120.1261 (3)1.0030 (6)0.4723 (4)0.0468 (16)
H12A0.10520.98840.41010.056*
H12B0.12611.08660.48370.056*
C130.0174 (2)0.9679 (4)0.4696 (3)0.0265 (11)
H130.00051.01720.41690.032*
C140.0832 (2)1.0082 (5)0.4942 (4)0.0374 (13)
H14A0.09910.96480.55010.045*
H14B0.08211.09030.51170.045*
C150.1273 (3)0.9910 (6)0.4098 (5)0.0453 (15)
H15A0.11381.04080.35620.054*
H15B0.17061.01340.42830.054*
C160.1269 (3)0.8681 (6)0.3778 (5)0.0532 (17)
H16A0.15490.85950.32160.064*
H16B0.14370.81930.42980.064*
C170.0622 (3)0.8286 (6)0.3522 (5)0.0532 (16)
H17A0.06380.74700.33340.064*
H17B0.04680.87310.29670.064*
C180.0161 (3)0.8432 (5)0.4363 (4)0.0394 (13)
H18A0.02710.82220.41580.047*
H18B0.02840.79210.48970.047*
C190.1037 (3)0.7770 (4)0.6926 (4)0.0377 (13)
C200.1590 (3)0.8229 (5)0.7266 (5)0.0515 (15)
H200.15710.88480.77070.062*
C210.2168 (3)0.7822 (7)0.6990 (6)0.067 (2)
H210.25420.81560.72410.081*
C220.2209 (4)0.6929 (7)0.6348 (6)0.075 (2)
H220.26060.66310.61570.090*
C230.1659 (4)0.6486 (6)0.5994 (6)0.073 (2)
H230.16800.58940.55290.088*
C240.1087 (3)0.6861 (4)0.6281 (4)0.0480 (15)
H240.07160.65030.60430.058*
C250.0691 (2)0.4456 (5)0.3995 (4)0.0340 (12)
H250.07320.48210.33510.041*
C260.1279 (2)0.3764 (5)0.4200 (4)0.0349 (12)
H26A0.12370.33770.48270.042*
H26B0.13330.31690.37020.042*
C270.1857 (2)0.4554 (5)0.4211 (5)0.0440 (14)
H27A0.19080.49170.35750.053*
H27B0.22400.40970.43440.053*
C280.1786 (3)0.5468 (6)0.4963 (5)0.0519 (16)
H28A0.17720.51090.56040.062*
H28B0.21550.59870.49410.062*
C290.1188 (3)0.6155 (5)0.4801 (6)0.0531 (17)
H29A0.11350.67090.53310.064*
H29B0.12280.65940.41980.064*
C300.0607 (3)0.5386 (4)0.4745 (4)0.0385 (13)
H30A0.02330.58560.45840.046*
H30B0.05320.50280.53770.046*
C310.0501 (2)0.4152 (4)0.3808 (4)0.0288 (11)
H310.05990.47010.43370.035*
C320.0527 (2)0.4797 (5)0.2867 (4)0.0374 (13)
H32A0.02320.54530.28850.045*
H32B0.04010.42850.23370.045*
C330.1202 (2)0.5229 (5)0.2703 (5)0.0481 (16)
H33A0.12250.56190.20750.058*
H33B0.13110.57950.32040.058*
C340.1676 (3)0.4259 (5)0.2727 (5)0.0485 (15)
H34A0.15900.37210.21960.058*
H34B0.21070.45700.26390.058*
C350.1638 (3)0.3629 (5)0.3673 (5)0.0454 (14)
H35A0.19370.29780.36690.054*
H35B0.17600.41520.41990.054*
C360.0975 (2)0.3186 (5)0.3847 (4)0.0361 (12)
H36A0.08680.26070.33550.043*
H36B0.09550.28120.44810.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0368 (6)0.0339 (6)0.0307 (6)0.0028 (6)0.0023 (7)0.0034 (6)
S20.0481 (8)0.0581 (10)0.0440 (9)0.0101 (7)0.0064 (7)0.0254 (8)
N10.032 (2)0.029 (2)0.020 (2)0.0034 (19)0.0018 (19)0.0016 (19)
N20.029 (2)0.031 (2)0.028 (2)0.0014 (19)0.0026 (18)0.001 (2)
C10.042 (3)0.035 (3)0.018 (2)0.002 (2)0.002 (2)0.004 (2)
C20.057 (4)0.035 (3)0.036 (3)0.002 (3)0.006 (3)0.001 (3)
C30.064 (4)0.051 (4)0.041 (4)0.026 (3)0.010 (3)0.005 (3)
C40.044 (3)0.065 (4)0.040 (3)0.003 (3)0.012 (3)0.011 (4)
C50.045 (3)0.039 (3)0.039 (3)0.001 (3)0.008 (3)0.000 (3)
C60.043 (3)0.033 (3)0.026 (3)0.002 (2)0.002 (2)0.003 (2)
C70.023 (2)0.034 (3)0.032 (3)0.005 (2)0.002 (2)0.006 (2)
C80.038 (3)0.061 (4)0.024 (3)0.001 (3)0.005 (2)0.004 (3)
C90.033 (3)0.086 (5)0.040 (3)0.004 (3)0.012 (3)0.003 (4)
C100.031 (3)0.108 (6)0.044 (4)0.014 (3)0.005 (3)0.002 (4)
C110.028 (3)0.122 (6)0.037 (4)0.004 (4)0.000 (2)0.007 (4)
C120.037 (3)0.073 (4)0.030 (3)0.004 (3)0.001 (3)0.001 (3)
C130.028 (3)0.029 (2)0.022 (2)0.000 (2)0.003 (2)0.003 (2)
C140.035 (3)0.054 (3)0.023 (3)0.004 (3)0.001 (2)0.000 (3)
C150.030 (3)0.074 (4)0.032 (3)0.007 (3)0.003 (2)0.002 (3)
C160.043 (3)0.075 (4)0.041 (4)0.020 (3)0.011 (3)0.002 (3)
C170.059 (4)0.055 (4)0.045 (4)0.019 (3)0.013 (3)0.010 (3)
C180.043 (3)0.037 (3)0.038 (3)0.002 (3)0.005 (3)0.002 (3)
C190.052 (3)0.033 (3)0.028 (3)0.001 (2)0.003 (3)0.012 (2)
C200.058 (4)0.058 (4)0.039 (3)0.015 (3)0.001 (3)0.006 (3)
C210.043 (4)0.088 (5)0.071 (5)0.003 (4)0.001 (3)0.024 (5)
C220.068 (5)0.077 (5)0.079 (6)0.014 (4)0.022 (4)0.028 (5)
C230.109 (6)0.053 (4)0.056 (4)0.022 (4)0.026 (5)0.012 (4)
C240.070 (4)0.031 (3)0.043 (4)0.005 (3)0.004 (3)0.000 (3)
C250.028 (3)0.041 (3)0.033 (3)0.009 (2)0.002 (2)0.003 (3)
C260.030 (3)0.039 (3)0.036 (3)0.008 (2)0.001 (2)0.010 (2)
C270.031 (3)0.055 (4)0.046 (4)0.002 (3)0.001 (3)0.000 (3)
C280.038 (3)0.058 (4)0.060 (4)0.015 (3)0.003 (3)0.004 (3)
C290.043 (3)0.044 (3)0.072 (5)0.010 (3)0.008 (3)0.000 (3)
C300.039 (3)0.030 (3)0.047 (3)0.002 (2)0.001 (3)0.002 (3)
C310.023 (2)0.034 (3)0.029 (3)0.001 (2)0.004 (2)0.002 (2)
C320.032 (3)0.038 (3)0.043 (3)0.002 (2)0.001 (3)0.006 (3)
C330.039 (3)0.053 (4)0.053 (4)0.002 (3)0.008 (3)0.009 (3)
C340.036 (3)0.058 (4)0.051 (4)0.001 (3)0.009 (3)0.000 (3)
C350.033 (3)0.054 (4)0.049 (4)0.009 (3)0.004 (3)0.003 (3)
C360.036 (3)0.038 (3)0.035 (3)0.005 (2)0.002 (2)0.002 (3)
Geometric parameters (Å, º) top
S1—C11.762 (5)C17—C181.539 (8)
S2—C191.755 (6)C17—H17A0.9900
N1—C131.498 (6)C17—H17B0.9900
N1—C71.497 (6)C18—H18A0.9900
N1—H1A0.92 (5)C18—H18B0.9900
N1—H1B0.93 (6)C19—C201.374 (8)
N2—C251.490 (6)C19—C241.397 (8)
N2—C311.507 (6)C20—C211.372 (9)
N2—H2A1.11 (5)C20—H200.9500
N2—H2B0.87 (6)C21—C221.378 (11)
C1—C61.387 (7)C21—H210.9500
C1—C21.389 (7)C22—C231.369 (11)
C2—C31.394 (8)C22—H220.9500
C2—H20.9500C23—C241.350 (9)
C3—C41.361 (9)C23—H230.9500
C3—H30.9500C24—H240.9500
C4—C51.377 (8)C25—C261.513 (7)
C4—H40.9500C25—C301.520 (8)
C5—C61.383 (7)C25—H251.0000
C5—H50.9500C26—C271.535 (7)
C6—H60.9500C26—H26A0.9900
C7—C81.490 (7)C26—H26B0.9900
C7—C121.500 (8)C27—C281.505 (9)
C7—H71.0000C27—H27A0.9900
C8—C91.523 (7)C27—H27B0.9900
C8—H8A0.9900C28—C291.517 (8)
C8—H8B0.9900C28—H28A0.9900
C9—C101.495 (9)C28—H28B0.9900
C9—H9A0.9900C29—C301.527 (7)
C9—H9B0.9900C29—H29A0.9900
C10—C111.520 (9)C29—H29B0.9900
C10—H10A0.9900C30—H30A0.9900
C10—H10B0.9900C30—H30B0.9900
C11—C121.512 (8)C31—C361.511 (7)
C11—H11A0.9900C31—C321.516 (7)
C11—H11B0.9900C31—H311.0000
C12—H12A0.9900C32—C331.535 (7)
C12—H12B0.9900C32—H32A0.9900
C13—C141.513 (7)C32—H32B0.9900
C13—C181.529 (7)C33—C341.514 (8)
C13—H131.0000C33—H33A0.9900
C14—C151.518 (8)C33—H33B0.9900
C14—H14A0.9900C34—C351.515 (9)
C14—H14B0.9900C34—H34A0.9900
C15—C161.504 (9)C34—H34B0.9900
C15—H15A0.9900C35—C361.518 (7)
C15—H15B0.9900C35—H35A0.9900
C16—C171.491 (9)C35—H35B0.9900
C16—H16A0.9900C36—H36A0.9900
C16—H16B0.9900C36—H36B0.9900
C13—N1—C7117.6 (4)C13—C18—C17109.0 (5)
C13—N1—H1A113 (3)C13—C18—H18A109.9
C7—N1—H1A102 (3)C17—C18—H18A109.9
C13—N1—H1B103 (3)C13—C18—H18B109.9
C7—N1—H1B113 (3)C17—C18—H18B109.9
H1A—N1—H1B109 (4)H18A—C18—H18B108.3
C25—N2—C31117.9 (4)C20—C19—C24117.1 (6)
C25—N2—H2A111 (3)C20—C19—S2121.6 (5)
C31—N2—H2A111 (3)C24—C19—S2121.3 (5)
C25—N2—H2B109 (4)C19—C20—C21122.0 (7)
C31—N2—H2B112 (4)C19—C20—H20119.0
H2A—N2—H2B93 (4)C21—C20—H20119.0
C6—C1—C2117.6 (5)C22—C21—C20120.1 (7)
C6—C1—S1121.3 (4)C22—C21—H21120.0
C2—C1—S1121.1 (4)C20—C21—H21120.0
C1—C2—C3121.0 (5)C23—C22—C21117.9 (7)
C1—C2—H2119.5C23—C22—H22121.0
C3—C2—H2119.5C21—C22—H22121.0
C4—C3—C2120.4 (5)C24—C23—C22122.4 (8)
C4—C3—H3119.8C24—C23—H23118.8
C2—C3—H3119.8C22—C23—H23118.8
C3—C4—C5119.4 (5)C23—C24—C19120.4 (6)
C3—C4—H4120.3C23—C24—H24119.8
C5—C4—H4120.3C19—C24—H24119.8
C4—C5—C6120.7 (5)N2—C25—C26108.0 (4)
C4—C5—H5119.6N2—C25—C30111.4 (4)
C6—C5—H5119.6C26—C25—C30110.3 (4)
C5—C6—C1120.8 (5)N2—C25—H25109.0
C5—C6—H6119.6C26—C25—H25109.0
C1—C6—H6119.6C30—C25—H25109.0
C8—C7—C12111.4 (4)C25—C26—C27109.9 (4)
C8—C7—N1108.9 (4)C25—C26—H26A109.7
C12—C7—N1112.3 (4)C27—C26—H26A109.7
C8—C7—H7108.0C25—C26—H26B109.7
C12—C7—H7108.0C27—C26—H26B109.7
N1—C7—H7108.0H26A—C26—H26B108.2
C7—C8—C9110.9 (5)C28—C27—C26110.7 (5)
C7—C8—H8A109.5C28—C27—H27A109.5
C9—C8—H8A109.5C26—C27—H27A109.5
C7—C8—H8B109.5C28—C27—H27B109.5
C9—C8—H8B109.5C26—C27—H27B109.5
H8A—C8—H8B108.0H27A—C27—H27B108.1
C10—C9—C8111.8 (5)C27—C28—C29110.8 (5)
C10—C9—H9A109.3C27—C28—H28A109.5
C8—C9—H9A109.3C29—C28—H28A109.5
C10—C9—H9B109.3C27—C28—H28B109.5
C8—C9—H9B109.3C29—C28—H28B109.5
H9A—C9—H9B107.9H28A—C28—H28B108.1
C9—C10—C11111.9 (5)C28—C29—C30111.8 (5)
C9—C10—H10A109.2C28—C29—H29A109.3
C11—C10—H10A109.2C30—C29—H29A109.3
C9—C10—H10B109.2C28—C29—H29B109.3
C11—C10—H10B109.2C30—C29—H29B109.3
H10A—C10—H10B107.9H29A—C29—H29B107.9
C12—C11—C10111.4 (5)C25—C30—C29111.2 (5)
C12—C11—H11A109.4C25—C30—H30A109.4
C10—C11—H11A109.4C29—C30—H30A109.4
C12—C11—H11B109.4C25—C30—H30B109.4
C10—C11—H11B109.4C29—C30—H30B109.4
H11A—C11—H11B108.0H30A—C30—H30B108.0
C7—C12—C11110.5 (5)C36—C31—N2108.1 (4)
C7—C12—H12A109.6C36—C31—C32112.2 (4)
C11—C12—H12A109.6N2—C31—C32111.4 (4)
C7—C12—H12B109.6C36—C31—H31108.3
C11—C12—H12B109.6N2—C31—H31108.3
H12A—C12—H12B108.1C32—C31—H31108.3
N1—C13—C14107.9 (4)C31—C32—C33109.1 (5)
N1—C13—C18110.7 (4)C31—C32—H32A109.9
C14—C13—C18112.5 (4)C33—C32—H32A109.9
N1—C13—H13108.6C31—C32—H32B109.9
C14—C13—H13108.6C33—C32—H32B109.9
C18—C13—H13108.6H32A—C32—H32B108.3
C13—C14—C15110.5 (4)C34—C33—C32111.7 (5)
C13—C14—H14A109.6C34—C33—H33A109.3
C15—C14—H14A109.6C32—C33—H33A109.3
C13—C14—H14B109.6C34—C33—H33B109.3
C15—C14—H14B109.6C32—C33—H33B109.3
H14A—C14—H14B108.1H33A—C33—H33B107.9
C16—C15—C14110.7 (5)C35—C34—C33110.3 (5)
C16—C15—H15A109.5C35—C34—H34A109.6
C14—C15—H15A109.5C33—C34—H34A109.6
C16—C15—H15B109.5C35—C34—H34B109.6
C14—C15—H15B109.5C33—C34—H34B109.6
H15A—C15—H15B108.1H34A—C34—H34B108.1
C17—C16—C15111.8 (5)C36—C35—C34110.8 (5)
C17—C16—H16A109.3C36—C35—H35A109.5
C15—C16—H16A109.3C34—C35—H35A109.5
C17—C16—H16B109.3C36—C35—H35B109.5
C15—C16—H16B109.3C34—C35—H35B109.5
H16A—C16—H16B107.9H35A—C35—H35B108.1
C16—C17—C18111.6 (5)C31—C36—C35110.9 (4)
C16—C17—H17A109.3C31—C36—H36A109.5
C18—C17—H17A109.3C35—C36—H36A109.5
C16—C17—H17B109.3C31—C36—H36B109.5
C18—C17—H17B109.3C35—C36—H36B109.5
H17A—C17—H17B108.0H36A—C36—H36B108.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···S1i0.92 (5)2.29 (6)3.200 (4)170 (4)
N1—H1B···S20.93 (6)2.37 (6)3.266 (5)163 (4)
N2—H2B···S1ii0.87 (6)2.34 (6)3.194 (5)167 (5)
N2—H2A···S2iii1.11 (5)2.15 (6)3.246 (5)166 (4)
Symmetry codes: (i) x, y+2, z+1/2; (ii) x, y+1, z+1/2; (iii) x, y+1, z1/2.

Experimental details

Crystal data
Chemical formulaC12H24N+·C6H5S
Mr291.50
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)200
a, b, c (Å)21.208 (4), 11.678 (2), 13.974 (3)
V3)3460.9 (12)
Z8
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.5 × 0.4 × 0.1
Data collection
DiffractometerOxford Diffraction KM-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3593, 3593, 2159
Rint0.000
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.144, 1.04
No. of reflections3593
No. of parameters373
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.30, 0.26
Absolute structureFlack (1983)
Absolute structure parameter0.06 (13)

Computer programs: KM4 System (Gałdecki, Kowalski & Uszyński, 1996), KM4 System, DATAPROC (Gałdecki, Kowalski, Kucharczyk & Uszyński, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), RESVIEW (Schwenk, 1998), SHELXL97.

Selected geometric parameters (Å, º) top
S1—C11.762 (5)N1—C71.497 (6)
S2—C191.755 (6)N2—C251.490 (6)
N1—C131.498 (6)N2—C311.507 (6)
C13—N1—C7117.6 (4)C13—N1—H1B103 (3)
C13—N1—H1A113 (3)C7—N1—H1B113 (3)
C7—N1—H1A102 (3)H1A—N1—H1B109 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···S1i0.92 (5)2.29 (6)3.200 (4)170 (4)
N1—H1B···S20.93 (6)2.37 (6)3.266 (5)163 (4)
N2—H2B···S1ii0.87 (6)2.34 (6)3.194 (5)167 (5)
N2—H2A···S2iii1.11 (5)2.15 (6)3.246 (5)166 (4)
Symmetry codes: (i) x, y+2, z+1/2; (ii) x, y+1, z+1/2; (iii) x, y+1, z1/2.
 

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