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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

n-Undeca­nyl 2-(4-chloro­anilino)-4,4-di­methyl-6-oxo­cyclo­hex-1-ene­carbo­di­thio­ate

aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 19 February 2009; accepted 19 February 2009; online 25 February 2009)

The six-membered cyclo­hexene ring in the title compound, C26H38ClNOS2, adopts an envelope conformation, with the C atom bearing the two methyl groups representing the flap. This atom deviates by 0.642 (4) Å from the plane passing through the other five atoms of the ring (r.m.s. deviation = 0.053 Å). The mol­ecular conformation is stabilized by an intra­molecular N—H⋯S hydrogen bond.

Related literature

For background, see: El Ashry et al. (2009[El Ashry, E. S. H., Amer, M. R., Raza Shah, M. & Ng, S. W. (2009). Acta Cryst. E65, o597.]).

[Scheme 1]

Experimental

Crystal data
  • C26H38ClNOS2

  • Mr = 480.14

  • Triclinic, [P \overline 1]

  • a = 7.9865 (2) Å

  • b = 11.8015 (4) Å

  • c = 14.9676 (4) Å

  • α = 97.522 (2)°

  • β = 94.004 (3)°

  • γ = 106.134 (2)°

  • V = 1335.13 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.32 mm−1

  • T = 100 K

  • 0.20 × 0.15 × 0.10 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.892, Tmax = 0.969

  • 12760 measured reflections

  • 6108 independent reflections

  • 3899 reflections with I > 2σ(I)

  • Rint = 0.051

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.157

  • S = 1.01

  • 6108 reflections

  • 287 parameters

  • 1 restraint

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

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯S2 0.89 (1) 2.10 (2) 2.873 (2) 146 (3)

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

For background, see: El Ashry et al. (2009).

Experimental top

To a solution of (4-chlorophenylamino)-5,5-dimethyl-cyclohex-2-en-1-one (0.1 mol) in DMSO (20 ml) and sodium hydroxide (0.4 g) in water (1 ml), carbon disulfphide (0.3 mol) was added in the course of 30 minutes. The mixture was stirred for 20 min below 283 K, and then 1-bromoundecane (0.1 mol) was added dropwise at room temperature for 30 min. The reaction mixture was left for 24 h and then diluted with water (200 ml) and acidified with 10% hydrochloric acid. The resulting precipitate was collected by filtration, dried and purified on silica gel column (40% ethyl acetate in hexane) to give yellow crystals (48% yield; mp 368 K).

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The methyl groups were allowed to rotate but not to tip.

The amino H-atom was located in a difference Fourier map, and was refined with a distance restraint of N–H 0.88±0.01 Å; its isotropic displacement parameter was freely refined.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) plot of C26H38ClNOS2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
n-Undecanyl 2-(4-chloroanilino)-4,4-dimethyl-6-oxocyclohex-1-enecarbodithioate top
Crystal data top
C26H38ClNOS2Z = 2
Mr = 480.14F(000) = 516
Triclinic, P1Dx = 1.194 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9865 (2) ÅCell parameters from 1537 reflections
b = 11.8015 (4) Åθ = 2.5–22.0°
c = 14.9676 (4) ŵ = 0.32 mm1
α = 97.522 (2)°T = 100 K
β = 94.004 (3)°Irregular block, yellow
γ = 106.134 (2)°0.20 × 0.15 × 0.10 mm
V = 1335.13 (7) Å3
Data collection top
Bruker SMART APEX
diffractometer
6108 independent reflections
Radiation source: fine-focus sealed tube3899 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
ω scansθmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.892, Tmax = 0.969k = 1515
12760 measured reflectionsl = 1919
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.074P)2]
where P = (Fo2 + 2Fc2)/3
6108 reflections(Δ/σ)max = 0.001
287 parametersΔρmax = 0.33 e Å3
1 restraintΔρmin = 0.36 e Å3
Crystal data top
C26H38ClNOS2γ = 106.134 (2)°
Mr = 480.14V = 1335.13 (7) Å3
Triclinic, P1Z = 2
a = 7.9865 (2) ÅMo Kα radiation
b = 11.8015 (4) ŵ = 0.32 mm1
c = 14.9676 (4) ÅT = 100 K
α = 97.522 (2)°0.20 × 0.15 × 0.10 mm
β = 94.004 (3)°
Data collection top
Bruker SMART APEX
diffractometer
6108 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3899 reflections with I > 2σ(I)
Tmin = 0.892, Tmax = 0.969Rint = 0.051
12760 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0521 restraint
wR(F2) = 0.157H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.33 e Å3
6108 reflectionsΔρmin = 0.36 e Å3
287 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.19825 (13)0.41121 (9)1.03994 (6)0.0563 (3)
S10.63724 (9)0.24958 (6)0.39696 (5)0.02316 (18)
S20.39872 (10)0.15853 (6)0.52890 (5)0.0290 (2)
N10.4552 (3)0.3457 (2)0.68108 (16)0.0254 (5)
H10.416 (4)0.2718 (14)0.651 (2)0.050 (11)*
O10.7692 (3)0.47573 (16)0.43665 (13)0.0286 (5)
C10.7341 (3)0.4897 (2)0.51557 (18)0.0212 (6)
C20.8197 (4)0.6096 (2)0.57245 (18)0.0244 (6)
H2A0.76350.66780.55140.029*
H2B0.94440.63540.56130.029*
C30.8122 (3)0.6156 (2)0.67421 (18)0.0230 (6)
C40.6254 (3)0.5507 (2)0.68855 (18)0.0221 (6)
H4A0.61870.54950.75420.027*
H4B0.54640.59600.66810.027*
C50.5613 (3)0.4250 (2)0.63920 (18)0.0230 (6)
C60.6116 (3)0.3932 (2)0.55220 (18)0.0218 (6)
C70.9411 (4)0.5570 (3)0.71535 (19)0.0300 (7)
H7A1.06070.59950.70530.045*
H7B0.91250.47340.68650.045*
H7C0.93290.56030.78060.045*
C80.8553 (4)0.7455 (3)0.7191 (2)0.0335 (7)
H8A0.76810.78120.69500.050*
H8B0.97210.78970.70630.050*
H8C0.85320.74910.78470.050*
C90.5498 (3)0.2748 (2)0.49969 (18)0.0228 (6)
C100.5423 (4)0.0905 (2)0.36058 (19)0.0275 (6)
H10A0.55280.04700.41200.033*
H10B0.41630.07270.33900.033*
C110.6397 (4)0.0507 (3)0.28414 (18)0.0278 (6)
H11A0.59100.03680.26590.033*
H11B0.76450.06730.30770.033*
C120.6303 (4)0.1104 (3)0.20027 (19)0.0297 (7)
H12A0.50570.09630.17760.036*
H12B0.68360.19760.21760.036*
C130.7230 (4)0.0651 (3)0.12447 (19)0.0297 (7)
H13A0.66510.02130.10470.036*
H13B0.84580.07460.14820.036*
C140.7234 (4)0.1293 (3)0.04282 (19)0.0319 (7)
H14A0.60060.11690.01760.038*
H14B0.77670.21600.06320.038*
C150.8222 (4)0.0882 (3)0.03191 (19)0.0334 (7)
H15A0.77560.00040.04890.040*
H15B0.94740.10700.00840.040*
C160.8086 (4)0.1459 (3)0.11602 (19)0.0305 (7)
H16A0.85720.23360.09900.037*
H16B0.68320.12850.13860.037*
C170.9041 (4)0.1038 (3)0.19232 (19)0.0312 (7)
H17A1.03070.12540.17090.037*
H17B0.86030.01560.20690.037*
C180.8816 (4)0.1564 (3)0.27808 (19)0.0294 (7)
H18A0.93280.24420.26440.035*
H18B0.75470.13960.29720.035*
C190.9668 (4)0.1080 (3)0.35609 (19)0.0323 (7)
H19A1.09460.12800.33830.039*
H19B0.91930.01980.36830.039*
C200.9360 (5)0.1577 (3)0.4419 (2)0.0421 (8)
H20A0.99420.12450.48990.063*
H20B0.98410.24490.43050.063*
H20C0.80980.13600.46100.063*
C210.3962 (4)0.3664 (3)0.76804 (19)0.0264 (6)
C220.2856 (4)0.4365 (3)0.7835 (2)0.0357 (8)
H220.25080.47500.73660.043*
C230.2256 (4)0.4507 (3)0.8673 (2)0.0420 (8)
H230.14990.49920.87830.050*
C240.2753 (4)0.3946 (3)0.9345 (2)0.0347 (7)
C250.3846 (5)0.3240 (3)0.9201 (2)0.0427 (8)
H250.41860.28560.96730.051*
C260.4448 (4)0.3095 (3)0.8357 (2)0.0375 (8)
H260.51960.26030.82460.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0583 (6)0.0751 (7)0.0282 (4)0.0072 (5)0.0165 (4)0.0020 (4)
S10.0251 (4)0.0190 (4)0.0240 (4)0.0041 (3)0.0038 (3)0.0034 (3)
S20.0293 (4)0.0188 (4)0.0367 (4)0.0013 (3)0.0120 (3)0.0042 (3)
N10.0269 (13)0.0211 (13)0.0272 (13)0.0033 (10)0.0097 (10)0.0046 (11)
O10.0343 (12)0.0214 (10)0.0270 (11)0.0011 (8)0.0093 (9)0.0049 (8)
C10.0183 (14)0.0177 (13)0.0273 (15)0.0042 (11)0.0019 (11)0.0047 (11)
C20.0249 (15)0.0189 (14)0.0279 (15)0.0030 (11)0.0029 (12)0.0057 (12)
C30.0183 (14)0.0236 (14)0.0250 (14)0.0032 (11)0.0022 (11)0.0029 (12)
C40.0216 (14)0.0201 (14)0.0246 (14)0.0058 (11)0.0032 (11)0.0032 (11)
C50.0196 (14)0.0222 (14)0.0283 (15)0.0070 (11)0.0006 (11)0.0073 (12)
C60.0198 (14)0.0220 (14)0.0235 (14)0.0059 (11)0.0011 (11)0.0047 (11)
C70.0241 (15)0.0379 (18)0.0269 (15)0.0068 (13)0.0003 (12)0.0074 (13)
C80.0330 (17)0.0254 (16)0.0369 (17)0.0019 (13)0.0055 (14)0.0002 (13)
C90.0191 (14)0.0242 (14)0.0277 (15)0.0091 (11)0.0026 (11)0.0065 (12)
C100.0314 (16)0.0199 (15)0.0272 (15)0.0008 (12)0.0024 (12)0.0041 (12)
C110.0332 (17)0.0244 (15)0.0253 (15)0.0097 (12)0.0011 (12)0.0004 (12)
C120.0337 (17)0.0267 (16)0.0270 (16)0.0070 (13)0.0015 (13)0.0031 (12)
C130.0298 (16)0.0285 (16)0.0271 (16)0.0060 (13)0.0014 (12)0.0013 (13)
C140.0371 (18)0.0296 (16)0.0280 (16)0.0092 (13)0.0035 (13)0.0024 (13)
C150.0361 (18)0.0376 (18)0.0279 (16)0.0133 (14)0.0041 (14)0.0039 (14)
C160.0324 (17)0.0280 (16)0.0305 (16)0.0094 (13)0.0029 (13)0.0017 (13)
C170.0295 (17)0.0364 (18)0.0276 (16)0.0101 (13)0.0026 (13)0.0043 (13)
C180.0297 (16)0.0261 (16)0.0322 (16)0.0072 (13)0.0042 (13)0.0058 (13)
C190.0274 (16)0.0376 (18)0.0333 (17)0.0079 (13)0.0072 (13)0.0117 (14)
C200.044 (2)0.051 (2)0.0373 (19)0.0168 (17)0.0141 (16)0.0157 (16)
C210.0242 (15)0.0273 (16)0.0250 (15)0.0036 (12)0.0038 (12)0.0029 (12)
C220.0321 (17)0.053 (2)0.0291 (16)0.0205 (15)0.0067 (13)0.0119 (15)
C230.0337 (18)0.065 (2)0.0345 (18)0.0235 (17)0.0114 (14)0.0077 (17)
C240.0323 (17)0.0421 (19)0.0229 (15)0.0004 (14)0.0097 (13)0.0004 (14)
C250.060 (2)0.040 (2)0.0296 (17)0.0152 (17)0.0037 (16)0.0102 (15)
C260.049 (2)0.0312 (18)0.0371 (18)0.0181 (15)0.0081 (15)0.0079 (14)
Geometric parameters (Å, º) top
Cl1—C241.740 (3)C12—H12B0.9900
S1—C91.757 (3)C13—C141.520 (4)
S1—C101.811 (3)C13—H13A0.9900
S2—C91.685 (3)C13—H13B0.9900
N1—C51.332 (3)C14—C151.517 (4)
N1—C211.429 (3)C14—H14A0.9900
N1—H10.885 (10)C14—H14B0.9900
O1—C11.234 (3)C15—C161.519 (4)
C1—C61.474 (4)C15—H15A0.9900
C1—C21.504 (4)C15—H15B0.9900
C2—C31.522 (4)C16—C171.522 (4)
C2—H2A0.9900C16—H16A0.9900
C2—H2B0.9900C16—H16B0.9900
C3—C41.520 (4)C17—C181.518 (4)
C3—C81.525 (4)C17—H17A0.9900
C3—C71.529 (4)C17—H17B0.9900
C4—C51.499 (4)C18—C191.519 (4)
C4—H4A0.9900C18—H18A0.9900
C4—H4B0.9900C18—H18B0.9900
C5—C61.423 (4)C19—C201.514 (4)
C6—C91.446 (4)C19—H19A0.9900
C7—H7A0.9800C19—H19B0.9900
C7—H7B0.9800C20—H20A0.9800
C7—H7C0.9800C20—H20B0.9800
C8—H8A0.9800C20—H20C0.9800
C8—H8B0.9800C21—C261.376 (4)
C8—H8C0.9800C21—C221.380 (4)
C10—C111.524 (4)C22—C231.380 (4)
C10—H10A0.9900C22—H220.9500
C10—H10B0.9900C23—C241.368 (4)
C11—C121.525 (4)C23—H230.9500
C11—H11A0.9900C24—C251.373 (5)
C11—H11B0.9900C25—C261.390 (4)
C12—C131.516 (4)C25—H250.9500
C12—H12A0.9900C26—H260.9500
C9—S1—C10102.95 (13)C12—C13—H13A108.9
C5—N1—C21127.5 (2)C14—C13—H13A108.9
C5—N1—H1116 (2)C12—C13—H13B108.9
C21—N1—H1116 (2)C14—C13—H13B108.9
O1—C1—C6121.4 (2)H13A—C13—H13B107.7
O1—C1—C2117.2 (2)C15—C14—C13114.0 (3)
C6—C1—C2121.4 (2)C15—C14—H14A108.8
C1—C2—C3116.1 (2)C13—C14—H14A108.8
C1—C2—H2A108.3C15—C14—H14B108.8
C3—C2—H2A108.3C13—C14—H14B108.8
C1—C2—H2B108.3H14A—C14—H14B107.7
C3—C2—H2B108.3C14—C15—C16113.2 (3)
H2A—C2—H2B107.4C14—C15—H15A108.9
C4—C3—C2107.3 (2)C16—C15—H15A108.9
C4—C3—C8108.7 (2)C14—C15—H15B108.9
C2—C3—C8109.7 (2)C16—C15—H15B108.9
C4—C3—C7110.5 (2)H15A—C15—H15B107.7
C2—C3—C7110.7 (2)C15—C16—C17113.9 (2)
C8—C3—C7109.9 (2)C15—C16—H16A108.8
C5—C4—C3113.6 (2)C17—C16—H16A108.8
C5—C4—H4A108.8C15—C16—H16B108.8
C3—C4—H4A108.8C17—C16—H16B108.8
C5—C4—H4B108.8H16A—C16—H16B107.7
C3—C4—H4B108.8C18—C17—C16113.7 (2)
H4A—C4—H4B107.7C18—C17—H17A108.8
N1—C5—C6122.3 (3)C16—C17—H17A108.8
N1—C5—C4116.4 (2)C18—C17—H17B108.8
C6—C5—C4121.3 (2)C16—C17—H17B108.8
C5—C6—C9124.1 (2)H17A—C17—H17B107.7
C5—C6—C1116.2 (2)C17—C18—C19113.5 (2)
C9—C6—C1119.7 (2)C17—C18—H18A108.9
C3—C7—H7A109.5C19—C18—H18A108.9
C3—C7—H7B109.5C17—C18—H18B108.9
H7A—C7—H7B109.5C19—C18—H18B108.9
C3—C7—H7C109.5H18A—C18—H18B107.7
H7A—C7—H7C109.5C20—C19—C18112.5 (3)
H7B—C7—H7C109.5C20—C19—H19A109.1
C3—C8—H8A109.5C18—C19—H19A109.1
C3—C8—H8B109.5C20—C19—H19B109.1
H8A—C8—H8B109.5C18—C19—H19B109.1
C3—C8—H8C109.5H19A—C19—H19B107.8
H8A—C8—H8C109.5C19—C20—H20A109.5
H8B—C8—H8C109.5C19—C20—H20B109.5
C6—C9—S2125.1 (2)H20A—C20—H20B109.5
C6—C9—S1117.8 (2)C19—C20—H20C109.5
S2—C9—S1117.15 (16)H20A—C20—H20C109.5
C11—C10—S1108.50 (19)H20B—C20—H20C109.5
C11—C10—H10A110.0C26—C21—C22120.1 (3)
S1—C10—H10A110.0C26—C21—N1118.4 (3)
C11—C10—H10B110.0C22—C21—N1121.4 (3)
S1—C10—H10B110.0C23—C22—C21119.8 (3)
H10A—C10—H10B108.4C23—C22—H22120.1
C10—C11—C12114.8 (2)C21—C22—H22120.1
C10—C11—H11A108.6C24—C23—C22119.9 (3)
C12—C11—H11A108.6C24—C23—H23120.1
C10—C11—H11B108.6C22—C23—H23120.1
C12—C11—H11B108.6C23—C24—C25121.1 (3)
H11A—C11—H11B107.5C23—C24—Cl1120.0 (3)
C13—C12—C11113.2 (2)C25—C24—Cl1119.0 (3)
C13—C12—H12A108.9C24—C25—C26119.1 (3)
C11—C12—H12A108.9C24—C25—H25120.4
C13—C12—H12B108.9C26—C25—H25120.4
C11—C12—H12B108.9C21—C26—C25120.0 (3)
H12A—C12—H12B107.7C21—C26—H26120.0
C12—C13—C14113.5 (2)C25—C26—H26120.0
O1—C1—C2—C3165.2 (2)C10—S1—C9—C6174.7 (2)
C6—C1—C2—C315.6 (4)C10—S1—C9—S25.8 (2)
C1—C2—C3—C445.9 (3)C9—S1—C10—C11166.72 (19)
C1—C2—C3—C8163.9 (2)S1—C10—C11—C1260.6 (3)
C1—C2—C3—C774.7 (3)C10—C11—C12—C13177.9 (2)
C2—C3—C4—C555.4 (3)C11—C12—C13—C14176.6 (3)
C8—C3—C4—C5174.0 (2)C12—C13—C14—C15177.6 (3)
C7—C3—C4—C565.3 (3)C13—C14—C15—C16175.3 (3)
C21—N1—C5—C6179.8 (3)C14—C15—C16—C17178.9 (3)
C21—N1—C5—C40.5 (4)C15—C16—C17—C18176.8 (3)
C3—C4—C5—N1144.5 (2)C16—C17—C18—C19176.1 (2)
C3—C4—C5—C635.7 (3)C17—C18—C19—C20177.6 (3)
N1—C5—C6—C92.0 (4)C5—N1—C21—C26116.3 (3)
C4—C5—C6—C9177.8 (2)C5—N1—C21—C2267.0 (4)
N1—C5—C6—C1178.1 (2)C26—C21—C22—C230.8 (5)
C4—C5—C6—C12.1 (4)N1—C21—C22—C23177.4 (3)
O1—C1—C6—C5171.1 (2)C21—C22—C23—C240.3 (5)
C2—C1—C6—C58.2 (4)C22—C23—C24—C250.0 (5)
O1—C1—C6—C98.8 (4)C22—C23—C24—Cl1179.4 (3)
C2—C1—C6—C9172.0 (2)C23—C24—C25—C260.1 (5)
C5—C6—C9—S24.6 (4)Cl1—C24—C25—C26179.3 (3)
C1—C6—C9—S2175.2 (2)C22—C21—C26—C250.9 (5)
C5—C6—C9—S1175.8 (2)N1—C21—C26—C25177.6 (3)
C1—C6—C9—S14.3 (3)C24—C25—C26—C210.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S20.89 (1)2.10 (2)2.873 (2)146 (3)

Experimental details

Crystal data
Chemical formulaC26H38ClNOS2
Mr480.14
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.9865 (2), 11.8015 (4), 14.9676 (4)
α, β, γ (°)97.522 (2), 94.004 (3), 106.134 (2)
V3)1335.13 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.32
Crystal size (mm)0.20 × 0.15 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.892, 0.969
No. of measured, independent and
observed [I > 2σ(I)] reflections
12760, 6108, 3899
Rint0.051
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.157, 1.01
No. of reflections6108
No. of parameters287
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.33, 0.36

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S20.89 (1)2.10 (2)2.873 (2)146 (3)
 

Acknowledgements

We thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationEl Ashry, E. S. H., Amer, M. R., Raza Shah, M. & Ng, S. W. (2009). Acta Cryst. E65, o597.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  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
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds