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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o229
https://doi.org/10.1107/S1600536807064872

(Z)-N-[2-(Di­methyl­ammonio)eth­yl]thio­acetamide chloride

Grzegorz Dutkiewicz,a Teresa Borowiaka* and Jarosław Spychałaa

aDepartment of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland
*Correspondence e-mail: borowiak@amu.edu.pl

(Received 28 November 2007; accepted 1 December 2007; online 12 December 2007)

The thio­amide and quaternary amine parts of the title compound, C6H15N2S+·Cl−, are mutually almost perpendicular, the dihedral angle being 80.6 (7)°. The thio­amide group is planar and adopts a Z conformation, whereas the amine end of the cation is in an extended conformation. In the supra­molecular structure, mol­ecules are linked into centrosymmetric dimers by two hydrogen bonds: N—Hamine⋯Cl and N—Hthio­amide⋯Cl.

Related literature

For details of the synthesis, see Spychała (2000[Spychała, J. (2000). Tetrahedron, 56, 7981-7986.], 2003[Spychała, J. (2003). Magn. Reson. Chem. 41, 169-176.]). For bond-length data, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data

  • C6H15N2S+·Cl−

  • Mr = 182.71

  • Triclinic, [P \overline 1]

  • a = 5.9935 (2) Å

  • b = 7.7461 (3) Å

  • c = 10.8253 (4) Å

  • α = 79.489 (3)°

  • β = 79.796 (3)°

  • γ = 87.863 (3)°

  • V = 486.32 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.55 mm−1

  • T = 292 (2) K

  • 0.6 × 0.2 × 0.2 mm
Data collection

  • Kuma KM-4 CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32.5. Oxford Diffraction Poland, Wrocław, Poland.]) Tmin = 0.785, Tmax = 1.000 (expected range = 0.704–0.897)

  • 4065 measured reflections

  • 2332 independent reflections

  • 1988 reflections with I > 2σ(I)

  • Rint = 0.008
Refinement

  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.089

  • S = 1.06

  • 2332 reflections

  • 127 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯Cl1 0.883 (9) 2.174 (10) 3.0285 (11) 162.9 (16)
N4—H4⋯Cl1i 0.863 (9) 2.325 (10) 3.1801 (12) 171.0 (16)
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: CrysAlis CCD (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32.5. Oxford Diffraction Poland, Wrocław, Poland.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32.5. Oxford Diffraction Poland, Wrocław, Poland.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: Stereochemical Workstation Operation Manual (Siemens 1989[Siemens (1989). Stereochemical Workstation Operation Manual. Release 3.4. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807064872/ng2404sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064872/ng2404Isup2.hkl

checkCIF report


Comment top

The structure of the title compound (I), is shown below. Dimensions are available in the archived CIF.

The asymmetric unit of the title compound, (I), consists of one [C6H15N2S]+cation and one chloride anion (Fig.1). The thioamide group is in Z configuration, its bond lengths are in agreement with the literature (Allen, 2002). The thioamide group is flat, the appropriate torsion angles adopt values close to 0° or 180° [S(5)—C(5)—N(4)—C(3) = τ1 = -0.5 (2)°, C(51)—C(5)—N(4)—C(3) = τ2 = -179.6 (1)°]. The quarternary amine end of the molecule is associated with conformational flexibility and it is apparent that the amine chain is in an almost extended conformation [C(12)—N(1)—C(2)—C(3) = τ3 = 177.0 (1)°] and moreover, it lies in a plane that is nearly orthogonal to the thioamide plane, the dihedral angle between the least-squares planes is 80.6 (7)°. On the other hand, the amine and thioamide functions are mutually gauche oriented [N(1)—C(2)—C(3)—N(4) = τ4 = 62.3 (2)°]. This conformation of the molecule causes some steric stress which is released by thioamide bond angles distortion from ideal values of 120°, e.g. the bond angles adopt values as follows: C(5)—N(4)—C(3) is 125.0 (1)°, S(5)—C(5)—N(4) 124.0 (1)°, C(3)—N(4)—H(4) 114.9 (1)°, C(51)—C(5)—N(4) 114.7 (1)°, although the sum of bond angles around C(5) and N(4) equals 360°. This diversity in bond angles seems to be the general property of amide and thioamide groups. The molecular conformation is stabilized by the intermolecular hydrogen bonds N—H···Cl which give rise to centrosymmetric dimers formation (Fig. 1). Each cation in the dimer participates in two hydrogen bonds to two chloride anions, N+—H(amine)···Cl- and N—H(thioamide)···Cl-.

In supramolecular structure the dimers are ordered along the [010] direction one after the another thus forming alternate hydrophilic and hydrophobic segments. In the hydrophilic segments the chloride anions that interact with the cations via hydrogen bonds are located, whereas the hydrophobic segments are formed by two ribbons connected by van der Waals forces. Along the third direction, [100], the cations form stacks as the most efficient close packing motifs with the chloride anions forming columns in the channels of the close packing achieved by the cations.

Related literature top

For details of the synthesis, see Spychała (2000, 2003). For related literature, see: Allen (2002).

Experimental top

Starting from thioacetamide and the appropriate diaminoalkane, the title compound was obtained by the transamination Wallach reaction by refluxing the reaction mixture in ethanol. The reaction was carried out under literature conditions described in the previous papers (Spychała 2000, 2003). Solvent: 2-propanol / diethyl ether. Single crystals were grown from the hot solution by slow cooling.

Refinement top

Hydrogen atoms were found from difference Fourier maps and refined except hydrogen atoms of three methyl groups, which were constrained to ride on their parent atom. The N—H distances were restrained to 0.88±0.01 Å.

Structure description top

The structure of the title compound (I), is shown below. Dimensions are available in the archived CIF.

The asymmetric unit of the title compound, (I), consists of one [C6H15N2S]+cation and one chloride anion (Fig.1). The thioamide group is in Z configuration, its bond lengths are in agreement with the literature (Allen, 2002). The thioamide group is flat, the appropriate torsion angles adopt values close to 0° or 180° [S(5)—C(5)—N(4)—C(3) = τ1 = -0.5 (2)°, C(51)—C(5)—N(4)—C(3) = τ2 = -179.6 (1)°]. The quarternary amine end of the molecule is associated with conformational flexibility and it is apparent that the amine chain is in an almost extended conformation [C(12)—N(1)—C(2)—C(3) = τ3 = 177.0 (1)°] and moreover, it lies in a plane that is nearly orthogonal to the thioamide plane, the dihedral angle between the least-squares planes is 80.6 (7)°. On the other hand, the amine and thioamide functions are mutually gauche oriented [N(1)—C(2)—C(3)—N(4) = τ4 = 62.3 (2)°]. This conformation of the molecule causes some steric stress which is released by thioamide bond angles distortion from ideal values of 120°, e.g. the bond angles adopt values as follows: C(5)—N(4)—C(3) is 125.0 (1)°, S(5)—C(5)—N(4) 124.0 (1)°, C(3)—N(4)—H(4) 114.9 (1)°, C(51)—C(5)—N(4) 114.7 (1)°, although the sum of bond angles around C(5) and N(4) equals 360°. This diversity in bond angles seems to be the general property of amide and thioamide groups. The molecular conformation is stabilized by the intermolecular hydrogen bonds N—H···Cl which give rise to centrosymmetric dimers formation (Fig. 1). Each cation in the dimer participates in two hydrogen bonds to two chloride anions, N+—H(amine)···Cl- and N—H(thioamide)···Cl-.

In supramolecular structure the dimers are ordered along the [010] direction one after the another thus forming alternate hydrophilic and hydrophobic segments. In the hydrophilic segments the chloride anions that interact with the cations via hydrogen bonds are located, whereas the hydrophobic segments are formed by two ribbons connected by van der Waals forces. Along the third direction, [100], the cations form stacks as the most efficient close packing motifs with the chloride anions forming columns in the channels of the close packing achieved by the cations.

For details of the synthesis, see Spychała (2000, 2003). For related literature, see: Allen (2002).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation Operation Manual (Siemens 1989) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. Dimer of (I) generated by N+—H(amine)···Cl- and N—H(thioamide)···Cl- hydrogen bonds (dashed lines). A view along the [100] direction, (Macrae et al., 2006).
(Z)-N-[2-(Dimethylammonio)ethyl]thioacetamide chloride top
Crystal data top
C6H15N2S+·Cl−Z = 2
Mr = 182.71F(000) = 196
Triclinic, P1Dx = 1.248 Mg m−3
a = 5.9935 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.7461 (3) ÅCell parameters from 2792 reflections
c = 10.8253 (4) Åθ = 2.7–29.6°
α = 79.489 (3)°µ = 0.55 mm−1
β = 79.796 (3)°T = 292 K
γ = 87.863 (3)°Block, colourless
V = 486.32 (3) Å30.6 × 0.2 × 0.2 mm
Data collection top
Kuma KM-4 CCD
diffractometer		2332 independent reflections
Radiation source: fine-focus sealed tube1988 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.008
Detector resolution: 8.1929 pixels mm-1θmax = 29.7°, θmin = 3.0°
ω–scanh = −8→6
Absorption correction: multi-scan
CrysAlis RED (Oxford Diffraction, 2007)		k = −10→10
Tmin = 0.785, Tmax = 1.000l = −14→11
4065 measured reflections
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0493P)2 + 0.0911P]
where P = (Fo2 + 2Fc2)/3
2332 reflections(Δ/σ)max = 0.001
127 parametersΔρmax = 0.36 e Å−3
0 restraintsΔρmin = −0.27 e Å−3
Crystal data top
C6H15N2S+·Cl−γ = 87.863 (3)°
Mr = 182.71V = 486.32 (3) Å3
Triclinic, P1Z = 2
a = 5.9935 (2) ÅMo Kα radiation
b = 7.7461 (3) ŵ = 0.55 mm−1
c = 10.8253 (4) ÅT = 292 K
α = 79.489 (3)°0.6 × 0.2 × 0.2 mm
β = 79.796 (3)°
Data collection top
Kuma KM-4 CCD
diffractometer		2332 independent reflections
Absorption correction: multi-scan
CrysAlis RED (Oxford Diffraction, 2007)		1988 reflections with I > 2σ(I)
Tmin = 0.785, Tmax = 1.000Rint = 0.008
4065 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.36 e Å−3
2332 reflectionsΔρmin = −0.27 e Å−3
127 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 > 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
Cl10.74439 (6)0.68184 (5)0.92798 (3)0.04695 (12)
N10.43953 (18)0.72292 (15)0.72918 (10)0.0369 (2)
C110.6186 (3)0.7621 (2)0.61349 (16)0.0529 (4)
H11A0.71430.66090.60680.073 (6)*
H11B0.70810.85930.62010.077 (7)*
H11C0.54890.79150.53900.070 (6)*
C120.3063 (3)0.8834 (2)0.75207 (18)0.0564 (4)
H12A0.40210.96610.77330.066 (6)*
H12C0.18220.85260.82120.062 (5)*
H12B0.24850.93510.67640.062 (5)*
C20.2817 (2)0.5793 (2)0.72500 (14)0.0401 (3)
C30.3998 (2)0.4127 (2)0.69463 (14)0.0417 (3)
N40.5321 (2)0.33438 (15)0.79089 (10)0.0377 (2)
C50.7308 (2)0.25637 (17)0.76729 (13)0.0368 (3)
C510.8327 (3)0.1849 (2)0.88345 (16)0.0541 (4)
H51A0.79440.06310.91140.134 (12)*
H51B0.77430.24910.95030.148 (13)*
H51C0.99450.19680.86300.127 (10)*
S50.86290 (6)0.23364 (6)0.62085 (4)0.05189 (14)
H10.511 (3)0.691 (2)0.7946 (13)0.052 (5)*
H2A0.180 (3)0.564 (2)0.8055 (18)0.052 (5)*
H2B0.192 (3)0.622 (2)0.6625 (17)0.046 (4)*
H3A0.290 (3)0.329 (2)0.6874 (17)0.055 (5)*
H3B0.502 (3)0.432 (2)0.6142 (17)0.043 (4)*
H40.468 (3)0.338 (2)0.8684 (10)0.048 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.03632 (18)0.0692 (3)0.03689 (19)−0.00237 (15)−0.00751 (13)−0.01194 (16)
N10.0340 (5)0.0447 (6)0.0327 (5)0.0040 (4)−0.0078 (4)−0.0072 (4)
C110.0460 (8)0.0653 (10)0.0444 (8)−0.0118 (7)0.0021 (6)−0.0092 (7)
C120.0601 (10)0.0474 (9)0.0606 (10)0.0114 (7)−0.0097 (8)−0.0103 (7)
C20.0302 (6)0.0497 (8)0.0408 (7)0.0019 (5)−0.0089 (5)−0.0064 (6)
C30.0405 (7)0.0499 (8)0.0383 (7)−0.0007 (6)−0.0128 (6)−0.0113 (6)
N40.0425 (6)0.0418 (6)0.0291 (5)0.0026 (5)−0.0063 (4)−0.0079 (4)
C50.0394 (6)0.0379 (7)0.0347 (6)−0.0031 (5)−0.0083 (5)−0.0080 (5)
C510.0602 (10)0.0614 (11)0.0432 (8)0.0134 (8)−0.0188 (7)−0.0091 (7)
S50.0402 (2)0.0778 (3)0.0386 (2)0.00595 (17)−0.00335 (15)−0.01740 (18)
Geometric parameters (Å, º) top
N1—C121.488 (2)C2—H2B0.943 (18)
N1—C111.4908 (18)C3—N41.4519 (18)
N1—C21.4988 (18)C3—H3A0.963 (19)
N1—H10.883 (9)C3—H3B0.962 (18)
C11—H11A0.9600N4—C51.3206 (18)
C11—H11B0.9600N4—H40.863 (9)
C11—H11C0.9600C5—C511.501 (2)
C12—H12A0.9600C5—S51.6786 (14)
C12—H12C0.9600C51—H51A0.9600
C12—H12B0.9600C51—H51B0.9600
C2—C31.510 (2)C51—H51C0.9600
C2—H2A0.960 (19)
C12—N1—C11111.02 (13)N1—C2—H2B107.7 (10)
C12—N1—C2109.51 (11)C3—C2—H2B109.2 (10)
C11—N1—C2113.73 (11)H2A—C2—H2B106.1 (15)
C12—N1—H1106.7 (12)N4—C3—C2112.06 (12)
C11—N1—H1106.5 (12)N4—C3—H3A109.3 (11)
C2—N1—H1109.1 (12)C2—C3—H3A109.9 (11)
N1—C11—H11A109.5N4—C3—H3B106.9 (10)
N1—C11—H11B109.5C2—C3—H3B112.5 (10)
H11A—C11—H11B109.5H3A—C3—H3B105.9 (15)
N1—C11—H11C109.5C5—N4—C3124.90 (12)
H11A—C11—H11C109.5C5—N4—H4120.4 (12)
H11B—C11—H11C109.5C3—N4—H4114.6 (12)
N1—C12—H12A109.5N4—C5—C51114.66 (12)
N1—C12—H12C109.5N4—C5—S5124.05 (10)
H12A—C12—H12C109.5C51—C5—S5121.28 (11)
N1—C12—H12B109.5C5—C51—H51A109.5
H12A—C12—H12B109.5C5—C51—H51B109.5
H12C—C12—H12B109.5H51A—C51—H51B109.5
N1—C2—C3114.08 (11)C5—C51—H51C109.5
N1—C2—H2A105.4 (11)H51A—C51—H51C109.5
C3—C2—H2A113.9 (11)H51B—C51—H51C109.5
C12—N1—C2—C3176.67 (13)C3—N4—C5—C51−179.64 (14)
C11—N1—C2—C351.81 (16)C3—N4—C5—S5−0.5 (2)
N1—C2—C3—N462.34 (16)S5—C5—N4—H4177.1 (14)
C2—C3—N4—C5−142.40 (13)C51—C5—N4—H4−2.1 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl10.88 (1)2.17 (1)3.0285 (11)163 (2)
N4—H4···Cl1i0.86 (1)2.33 (1)3.1801 (12)171 (2)
Symmetry code: (i) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formulaC6H15N2S+·Cl−
Mr182.71
Crystal system, space groupTriclinic, P1
Temperature (K)292
a, b, c (Å)5.9935 (2), 7.7461 (3), 10.8253 (4)
α, β, γ (°)79.489 (3), 79.796 (3), 87.863 (3)
V (Å3)486.32 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.55
Crystal size (mm)0.6 × 0.2 × 0.2
Data collection
DiffractometerKuma KM-4 CCD
Absorption correctionMulti-scan
CrysAlis RED (Oxford Diffraction, 2007)
Tmin, Tmax0.785, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		4065, 2332, 1988
Rint0.008
(sin θ/λ)max (Å−1)0.697
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.089, 1.06
No. of reflections2332
No. of parameters127
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.36, −0.27

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), Stereochemical Workstation Operation Manual (Siemens 1989) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl10.883 (9)2.174 (10)3.0285 (11)162.9 (16)
N4—H4···Cl1i0.863 (9)2.325 (10)3.1801 (12)171.0 (16)
Symmetry code: (i) −x+1, −y+1, −z+2.
 

Acknowledgements

This work was supported by funds from Adam Mickiewicz University, Faculty of Chemistry.

References

First citationAllen, F. H. (2002). Acta Cryst. B58, 380–388.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationOxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32.5. Oxford Diffraction Poland, Wrocław, Poland.  Google Scholar
 First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationSiemens (1989). Stereochemical Workstation Operation Manual. Release 3.4. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationSpychała, J. (2000). Tetrahedron, 56, 7981–7986.  Google Scholar
 First citationSpychała, J. (2003). Magn. Reson. Chem. 41, 169–176.  Web of Science CrossRef Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o229
https://doi.org/10.1107/S1600536807064872
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