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Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296

S-Ethyl N-(4-chloro­benzoyl)­di­thio­carbamate: sheets built from π-stacked hydrogen-bonded chains

CROSSMARK_Color_square_no_text.svg

aDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, bDepartamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain, cDepartamento de Química, Universidad de Nariño, Cuidad Universitaria, Torobajo, AA1175 Pasto, Colombia, dGrupo de Investigación de Compuestos Heterociclícos, Departamento de Química, Universidad de Valle, AA 25360 Cali, Colombia, and eSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
*Correspondence e-mail: che562@abdn.ac.uk

(Received 8 November 2004; accepted 11 November 2004; online 11 December 2004)

Molecules of the title compound, C10H10ClNOS2, are linked into C(4) chains by an N—H⋯O hydrogen bond [H⋯O = 2.16 Å, N⋯O = 3.013 (3) Å and N—H⋯O = 176°], and the chains are linked into sheets by a centrosymmetric ππ stacking interaction.

Comment

S-Alkyl N-aroyldi­thio­carbamates are utilized in the preparation of S,S-di­alkyl N-aroyl­imino­di­thio­carbonates, which are themselves useful intermediates for organic synthesis (Augustín et al., 1980[Augustín, M., Richter, M. & Salas, S. (1980). J. Prakt. Chem. 322, 55-68.]). We report here the molecular and supramolecular structures of the title compound, (I[link]) (Fig. 1[link]), which differ in several respects from those of the unsubstituted analogue (II[link]) (Low et al., 2004[Low, J. N., Cobo, J., Insuasty, H., Estrada, M., Cortés, E. & Glidewell, C. (2004). Acta Cryst. C60, o483-o485.]). Compound (I[link]) crystallizes in space group P21/c with Z′ = 1, whereas (II[link]) crystallizes in C2/c with Z′ = 2. While the corresponding bond distances and angles in (I[link]) and (II[link]) are very similar, the molecular conformations adopted by the S-ethyl substituent are different. For the independent mol­ecules in (II[link]), the C—S—C—C torsion angles are both close to 180°, but in (I[link]) this angle is only 82.5 (3)° (Fig. 1[link]).

The most striking difference between (I[link]) and (II[link]) lies in their supramolecular aggregations. In (I[link]), this is dominated by a nearly linear N—H⋯O hydrogen bond (Table 1[link]), which gives rise to a C(4) chain (Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) running parallel to the [001] direction and generated by the c-glide plane at y = [1 \over4] (Fig. 2[link]). There is also a short intermolecular C—H⋯O contact involving the same two mol­ecules (Table 1[link]), but this is probably just an adventitious consequence of the N—H⋯O hydrogen bond. A second [001] chain, related to the first by inversion, is generated by the c-glide plane at y = [3 \over4].

The [001] chains in (I[link]) are weakly linked into sheets by an aromatic ππ stacking interaction. The aryl rings of the mol­ecules at (x, y, z) and (1 − x, 1 − y, 1 − z), which form parts of the chains along y = [1\over4] and y = [3 \over4], respectively, are strictly parallel; the interplanar spacing is 3.464 (2) Å and the ring-centroid separation is 3.865 (2) Å, corresponding to a ring-centroid offset of 1.714 (2) Å. Propagation of this interaction then links the [001] chains into a (100) sheet (Fig. 3[link]); there are no direction-specific interactions between adjacent sheets.

[Scheme 1]

There is a Cl⋯Cl contact involving mol­ecules at (x, y, z) and (1 − x, 2 − y, 1 − z), with a Cl⋯Cl distance of 3.135 (2) Å and a C—Cl⋯Cl angle of 165.5 (2)°; however, these two mol­ecules lie in the same (100) sheet. The Cl⋯Cl distance is certainly shorter than the sum of the van der Waals radii (3.52 Å) given by Bondi (1964[Bondi, A. (1964). J. Phys. Chem. 68, 441-451.]); however, the sum of the minor radii in the polar flattening model (Nyburg & Faerman, 1985[Nyburg, S. C. & Faerman, C. H. (1985). Acta Cryst. B41, 274-279.]) is only 3.16 Å, so this contact may be of limited significance. Nonetheless, the C—Cl⋯Cl angle is consistent with the results of a database analysis (Ramasubbu et al., 1986[Ramasubbu, N., Parthasarathy, R. & Murray-Rust, P. (1986). J. Am. Chem. Soc. 108, 4308-4314.]), which showed that such angles fall into two clusters, one around 90° and the other around 180°.

By contrast, the hydrogen bonding in (II[link]) does not involve the O atom at all; instead, the primary aggregation is dominated by the formation, by means of pairs of N—H⋯S hydrogen bonds, of two independent R22(8) dimers, one generated by inversion and the other generated by a twofold screw axis. These two independent dimers are then linked into chains by a single C—H⋯π(arene) hydrogen bond. Thus, the types of intermolecular interaction manifested in the supramolecular aggregation in (I[link]) and (II[link]) are entirely different; it is striking that the introduction of a remote substituent is associated with such a difference in the nature of the hydrogen bonding.

[Figure 1]
Figure 1
The mol­ecule of (I[link]), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2]
Figure 2
Part of the crystal structure of (I[link]), showing the formation of a hydrogen-bonded C(4) chain along [001]. For clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x, 1 − y, −[1\over2] + z) and (x, 1 − y, [1\over2] + z), respectively.
[Figure 3]
Figure 3
A stereoview of part of the crystal structure of (I[link]), showing the formation of a (100) sheet of π-stacked [001] chains. For clarity, H atoms bonded to C atoms have been omitted.

Experimental

4-Chloro­benzoyl chloride (5.5 ml, 0.043 mol) was added to a solution of potassium thio­cyanate (4.1 g, 0.043 mol) in aceto­nitrile (75 ml); this mixture was heated under reflux for 15 min to afford 4-chloro­benzoyl iso­thio­cyanate, which was not isolated. After cooling the intermediate solution to 273 K under an inert atmosphere, ethane­thiol (35 ml, 0.47 mol) was added, and this mixture was then stirred at room temperature for 27 h. Ice-water was added and the title compound was extracted with ethyl acetate (3 × 25 ml). The combined organic extracts were dried over an­hydrous sodium sulfate and the solvent was then removed under reduced pressure. The resulting yellow solid was recrystallized from ethanol to give crystals of (I[link]) suitable for single-crystal X-ray diffraction (yield 89%, m.p. 398 K).

Crystal data
  • C10H10ClNOS2

  • Mr = 259.76

  • Monoclinic, P21/c

  • a = 14.4020 (7) Å

  • b = 9.1110 (14) Å

  • c = 9.7040 (13) Å

  • β = 108.484 (8)°

  • V = 1207.6 (3) Å3

  • Z = 4

  • Dx = 1.429 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 2756 reflections

  • θ = 5.0–27.5°

  • μ = 0.63 mm−1

  • T = 120 (2) K

  • Block, colourless

  • 0.41 × 0.28 × 0.23 mm

Data collection
  • Nonius KappaCCD area-detector diffractometer

  • φ and ω scans

  • Absorption correction: multi-scan (EvalCCD; Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]) Tmin = 0.781, Tmax = 0.868

  • 22 106 measured reflections

  • 2756 independent reflections

  • 1334 reflections with I > 2σ(I)

  • Rint = 0.136

  • θmax = 27.5°

  • h = −18 → 18

  • k = −11 → 11

  • l = −12 → 12

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.139

  • S = 1.00

  • 2756 reflections

  • 137 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0655P)2 + 0.0228P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bonding geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯O1i 0.86 2.16 3.013 (3) 176
C12—H12⋯O1i 0.93 2.50 3.070 (3) 120
Symmetry code: (i) [x,{\script{1\over 2}}-y,z-{\script{1\over 2}}].

The space group P21/c was uniquely assigned from the systematic absences. All H atoms were located from difference maps and then treated as riding atoms, with C—H distances of 0.93 (aromatic), 0.96 (CH3) and 0.97 Å (CH2), and N—H distances of 0.86 Å, and with Uiso(H) values of 1.2Ueq(C,N) or 1.5Ueq(Cmethyl).

Data collection: COLLECT (Hooft, 1999[Hooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000[Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898.]); data reduction: EvalCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); 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.]); program(s) used to refine structure: OSCAIL (McArdle, 2003[McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.]) and SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999[Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.]).

Supporting information


Comment top

S-Alkyl N-aroyldithiocarbamates are utilized in the preparation of S,S-dialkyl N-aroyliminodithiocarbonates, which are themselves useful intermediates for organic synthesis (Augustín et al., 1980). We report here the molecular and supramolecular structures of the title compound, (I) (Fig. 1), which differ in several respects from those of the unsubstituted analogue, (II) (Low et al., 2004). Compound (I) crystallizes in space group P21/c with Z' = 1, whereas (II) crystallizes in C2/c with Z' = 2. While the corresponding bond distances and angles in (I) and (II) are very similar, the molecular conformations adopted by the S-ethyl substituent are different. For the independent molecules in (II), the C—S—C—C torsion angles are both close to 180°, but in (I) this angle is only 82.5 (3)° (Fig. 1).

The most striking difference between (I) and (II) lies in their supramolecular aggregation. In (I), this is dominated by a nearly linear N—H···O hydrogen bond (Table 1), which gives rise to a C(4) chain (Bernstein et al., 1995) running parallel to the [001] direction and generated by the c-glide plane at y = 0.25 (Fig. 2). There is also a short intermolecular C—H···O contact involving the same two molecules (Table 1), but this is probably just an adventitious consequence of the N—H···O hydrogen bond. A second [001] chain, related to the first by inversion, is generated by the c-glide plane at y = 0.75.

The [001] chains in (I) are weakly linked into sheets by an aromatic ππ stacking interaction. The aryl rings of the molecules at (x, y, z) and (1 − x, 1 − y, 1 − z), which form parts of the chains along y = 0.25 and y = 0.75 respectively, are strictly parallel; the interplanar spacing is 3.464 (2) Å and the ring-centroid separation is 3.865 (2) Å, corresponding to a ring-centroid offset of 1.714 (2) Å. Propagation of this interaction then links the [001] chains into a (100) sheet (Fig. 3); there are no direction-specific interactions between adjacent sheets.

There is a Cl···Cl contact involving molecules at (x, y, z) and (1 − x, 2 − y, 1 − z), with a Cl···Cli distance of 3.135 (2) Å and a C—Cl···Cli angle of 165.5 (2)° [symmetry code: (i) 1 − x, 2 − y, 1 − z]; however, these two molecules lie in the same (100) sheet. The Cl···Cl distance is certainly shorter than the sum of the van der Waals radii (3.52 Å) given by Bondi (1964); however, the sum of the minor radii in the polar flattening model (Nyburg & Faerman, 1985) is only 3.16 Å, so this contact may be of limited significance. Nonetheless, the C—Cl···Cl angle is consistent with the results of a database analysis (Ramasubbu et al., 1986), which showed that such angles fall into two clusters, one around 90° and the other around 180°.

By contrast, the hydrogen bonding in (II) does not involve the O atom at all; instead, the primary aggregation is dominated by the formation, by means of pairs of N—H···S hydrogen bonds, of two independent R22(8) dimers, one generated by inversion and the other generated by a twofold screw axis. These two independent dimers are then linked into chains by a single C—H···π(arene) hydrogen bond. Thus the types of intermolecular interaction manifested in the supramolecular aggregation in (I) and (II) are entirely different; it is striking that the introduction of a remote substituent is associated with such a difference in the nature of the hydrogen bonding.

Experimental top

4-Chlorobenzoyl chloride (5.5 ml, 0.043 mol) was added to a solution of potassium thiocyanate (4.1 g, 0.043 mol) in acetonitrile (75 ml); this mixture was heated under reflux for 15 min to afford 4-chlorobenzoyl isothiocyanate, which was not isolated. After cooling the intermediate solution to 273 K under an inert atmosphere, ethanethiol (35 ml, 0.47 mol) was added, and this mixture was then stirred at room temperature for 27 h. Ice-water was added and the title compound was extracted with ethyl acetate (3 × 25 ml). The combined organic extracts were dried over anhydrous sodium sulfate and the solvent was then removed under reduced pressure. The resulting yellow solid was recrystallized from ethanol to give crystals of (I), suitable for single-crystal X-ray diffraction (yield 89%, m.p. 398 K).

Refinement top

The space group P21/c was uniquely assigned from the systematic absences. All H atoms were located from difference maps, and then treated as riding atoms with C—H distances of 0.93 (aromatic), 0.96 (CH3) and 0.97 Å (CH2), and N—H distances of 0.86 Å, with Uiso(H) values of 1.2Ueq(C,N) or 1.5Ueq(Cmethyl).

Computing details top

Data collection: COLLECT (Hooft, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: OSCAIL (McArdle, 2003)? and SIR97 (Altomare et al., 1999); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. The molecule of (I), showing the atom-labelling scheme. Displacememt ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of a hydrogen-bonded C(4) chain along [001]. For clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x, 1 − y, −0.5 + z) and (x, 1 − y, 0.5 + z), respectively.
[Figure 3] Fig. 3. A stereoview of part of the crystal structure of (I), showing the formation of a (100) sheet of π-stacked [001] chains. For clarity, H atoms bonded to C atoms have been omitted.
S-Ethyl N-(4-chlorobenzoyl)dithiocarbamate top
Crystal data top
C10H10ClNOS2F(000) = 536
Mr = 259.76Dx = 1.429 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2756 reflections
a = 14.4020 (7) Åθ = 5.0–27.5°
b = 9.1110 (14) ŵ = 0.63 mm1
c = 9.7040 (13) ÅT = 120 K
β = 108.484 (8)°Block, colourless
V = 1207.6 (3) Å30.41 × 0.28 × 0.23 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
2756 independent reflections
Radiation source: fine-focus sealed X-ray tube1334 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.136
ϕ and ω scansθmax = 27.5°, θmin = 5.0°
Absorption correction: multi-scan
(EVALCCD; Duisenberg et al., 2003)
h = 1818
Tmin = 0.781, Tmax = 0.868k = 1111
22106 measured reflectionsl = 1212
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0655P)2 + 0.0228P]
where P = (Fo2 + 2Fc2)/3
2756 reflections(Δ/σ)max < 0.001
137 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C10H10ClNOS2V = 1207.6 (3) Å3
Mr = 259.76Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.4020 (7) ŵ = 0.63 mm1
b = 9.1110 (14) ÅT = 120 K
c = 9.7040 (13) Å0.41 × 0.28 × 0.23 mm
β = 108.484 (8)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
2756 independent reflections
Absorption correction: multi-scan
(EVALCCD; Duisenberg et al., 2003)
1334 reflections with I > 2σ(I)
Tmin = 0.781, Tmax = 0.868Rint = 0.136
22106 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.139H-atom parameters constrained
S = 1.00Δρmax = 0.35 e Å3
2756 reflectionsΔρmin = 0.33 e Å3
137 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl140.55581 (8)0.85530 (10)0.56450 (11)0.0789 (4)
S30.84470 (9)0.00157 (13)0.47246 (11)0.0873 (4)
S40.82619 (7)0.03878 (10)0.76842 (10)0.0642 (3)
O10.70464 (16)0.1825 (2)0.7886 (2)0.0560 (6)
N20.74835 (16)0.1775 (3)0.5837 (2)0.0425 (6)
C10.7079 (2)0.2449 (3)0.6787 (3)0.0409 (7)
C30.8033 (2)0.0508 (3)0.6028 (3)0.0465 (8)
C50.9118 (3)0.1788 (4)0.7599 (5)0.0806 (12)
C61.0153 (3)0.1250 (6)0.8008 (6)0.127 (2)
C110.66898 (19)0.3941 (3)0.6409 (3)0.0374 (7)
C120.7049 (2)0.4906 (3)0.5601 (3)0.0417 (7)
C130.6706 (2)0.6326 (3)0.5368 (3)0.0484 (8)
C140.5995 (2)0.6772 (3)0.5940 (3)0.0488 (8)
C150.5618 (2)0.5839 (4)0.6744 (3)0.0529 (8)
C160.5975 (2)0.4425 (4)0.6981 (3)0.0495 (8)
H20.73790.22070.50140.051*
H5A0.90840.25830.82460.097*
H5B0.89310.21790.66190.097*
H6A1.05610.20040.78160.191*
H6B1.03800.10080.90230.191*
H6C1.01820.03930.74470.191*
H120.75270.45930.52110.050*
H130.69530.69730.48300.058*
H150.51320.61540.71190.064*
H160.57340.37860.75330.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl140.1020 (7)0.0495 (6)0.0965 (7)0.0314 (5)0.0472 (6)0.0161 (5)
S30.1175 (9)0.0928 (9)0.0616 (6)0.0554 (7)0.0424 (6)0.0056 (5)
S40.0758 (6)0.0578 (6)0.0646 (6)0.0219 (5)0.0301 (5)0.0194 (4)
O10.0875 (16)0.0429 (13)0.0467 (13)0.0105 (11)0.0343 (12)0.0067 (10)
N20.0560 (15)0.0378 (15)0.0353 (13)0.0097 (12)0.0167 (12)0.0035 (11)
C10.0497 (17)0.0372 (18)0.0364 (16)0.0010 (14)0.0143 (14)0.0019 (14)
C30.0488 (17)0.0433 (19)0.0478 (18)0.0062 (15)0.0157 (15)0.0002 (14)
C50.090 (3)0.065 (3)0.094 (3)0.034 (2)0.041 (2)0.027 (2)
C60.077 (3)0.147 (6)0.147 (5)0.039 (3)0.022 (3)0.014 (4)
C110.0421 (16)0.0376 (17)0.0339 (15)0.0032 (13)0.0139 (14)0.0003 (12)
C120.0482 (17)0.0394 (18)0.0434 (16)0.0046 (14)0.0230 (14)0.0028 (14)
C130.0559 (19)0.040 (2)0.0551 (19)0.0024 (15)0.0259 (16)0.0060 (15)
C140.0585 (19)0.0383 (19)0.0489 (18)0.0130 (15)0.0161 (16)0.0013 (15)
C150.0588 (19)0.052 (2)0.058 (2)0.0190 (17)0.0325 (17)0.0046 (17)
C160.0559 (19)0.049 (2)0.0509 (19)0.0049 (16)0.0274 (16)0.0065 (15)
Geometric parameters (Å, º) top
C1—O11.222 (3)C16—H160.93
C1—N21.381 (3)N2—C31.379 (4)
C1—C111.471 (4)N2—H20.86
C11—C121.383 (4)C3—S31.631 (3)
C11—C161.387 (4)C3—S41.738 (3)
C12—C131.377 (4)S4—C51.794 (4)
C12—H120.93C5—C61.498 (6)
C13—C141.373 (4)C5—H5A0.97
C13—H130.93C5—H5B0.97
C14—C151.377 (4)C6—H6A0.96
C14—Cl141.731 (3)C6—H6B0.96
C15—C161.379 (4)C6—H6C0.96
C15—H150.93
O1—C1—N2121.1 (3)C11—C16—H16119.5
O1—C1—C11122.0 (2)C3—N2—C1129.0 (2)
N2—C1—C11116.9 (2)C3—N2—H2115.6
C12—C11—C16118.9 (3)C1—N2—H2115.5
C12—C11—C1123.2 (2)N2—C3—S3118.4 (2)
C16—C11—C1117.8 (2)N2—C3—S4116.7 (2)
C13—C12—C11120.8 (3)S3—C3—S4124.84 (18)
C13—C12—H12119.6C3—S4—C5102.85 (17)
C11—C12—H12119.6C6—C5—S4113.3 (3)
C14—C13—C12119.1 (3)C6—C5—H5A108.9
C14—C13—H13120.4S4—C5—H5A108.9
C12—C13—H13120.4C6—C5—H5B108.9
C13—C14—C15121.7 (3)S4—C5—H5B108.9
C13—C14—Cl14119.3 (2)H5A—C5—H5B107.7
C15—C14—Cl14119.0 (2)C5—C6—H6A109.5
C14—C15—C16118.6 (3)C5—C6—H6B109.5
C14—C15—H15120.7H6A—C6—H6B109.5
C16—C15—H15120.7C5—C6—H6C109.5
C15—C16—C11121.0 (3)H6A—C6—H6C109.5
C15—C16—H16119.5H6B—C6—H6C109.5
O1—C1—C11—C12151.7 (3)C14—C15—C16—C110.9 (5)
N2—C1—C11—C1228.5 (4)C12—C11—C16—C150.6 (4)
O1—C1—C11—C1623.7 (4)C1—C11—C16—C15176.2 (3)
N2—C1—C11—C16156.1 (3)O1—C1—N2—C311.8 (5)
C16—C11—C12—C130.1 (4)C11—C1—N2—C3168.4 (3)
C1—C11—C12—C13175.3 (3)C1—N2—C3—S3178.3 (2)
C11—C12—C13—C140.5 (4)C1—N2—C3—S40.1 (4)
C12—C13—C14—C150.2 (5)N2—C3—S4—C5172.2 (2)
C12—C13—C14—Cl14179.8 (2)S3—C3—S4—C55.9 (3)
C13—C14—C15—C160.5 (5)C3—S4—C5—C682.5 (3)
Cl14—C14—C15—C16179.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.862.163.013 (3)176
C12—H12···O1i0.932.503.070 (3)120
Symmetry code: (i) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC10H10ClNOS2
Mr259.76
Crystal system, space groupMonoclinic, P21/c
Temperature (K)120
a, b, c (Å)14.4020 (7), 9.1110 (14), 9.7040 (13)
β (°) 108.484 (8)
V3)1207.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.63
Crystal size (mm)0.41 × 0.28 × 0.23
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(EVALCCD; Duisenberg et al., 2003)
Tmin, Tmax0.781, 0.868
No. of measured, independent and
observed [I > 2σ(I)] reflections
22106, 2756, 1334
Rint0.136
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.139, 1.00
No. of reflections2756
No. of parameters137
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.33

Computer programs: COLLECT (Hooft, 1999), DIRAX/LSQ (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003), OSCAIL (McArdle, 2003)? and SIR97 (Altomare et al., 1999), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.862.163.013 (3)176
C12—H12···O1i0.932.503.070 (3)120
Symmetry code: (i) x, y+1/2, z1/2.
 

Footnotes

Correspondence address: Department of Electrical Engineering and Physics, School of Engineering and Physical Science, University of Dundee, Dundee DD1 4HN, Scotland.

Acknowledgements

X-ray data were collected at the `Servicios Técnicos de Investigación', University of Jaén. JC thanks the Consejería de Educación y Ciencia (Junta de Andalucía, Spain) and the Universidad de Jaén for financial support. HI, ME and EC thank COLCIENCIAS and UDENAR (Universidad de Nariño) for financial support. BI thanks COLCIENCIAS and UNIVALLE (Universidad del Valle) for financial support. JNL thanks NCR Self-Service, Dundee, for grants which have provided computing facilities for this work.

References

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