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ISSN: 2056-9890

n-Undeca­nyl 2-(2,4-di­chloro­anilino)-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;eelashry60@hotmail.com

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

The six-membered cyclo­hexene ring in the title compound, C26H37Cl2NOS2, adopts an envelope-shaped conformation, with the C atom bearing the two methyl groups representing the flap. This atom deviates by 0.658 (7) Å from the plane passing through the other five atoms of the ring (r.m.s. deviation = 0.005 Å). The mol­ecular conformation is stabilized by an 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
  • C26H37Cl2NOS2

  • Mr = 514.59

  • Orthorhombic, P n a 21

  • a = 14.6145 (4) Å

  • b = 31.378 (1) Å

  • c = 5.9332 (2) Å

  • V = 2720.8 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.41 mm−1

  • T = 100 K

  • 0.30 × 0.20 × 0.02 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.665, Tmax = 0.992

  • 24605 measured reflections

  • 6244 independent reflections

  • 4130 reflections with I > 2σ(I)

  • Rint = 0.084

Refinement
  • R[F2 > 2σ(F2)] = 0.064

  • wR(F2) = 0.177

  • S = 1.05

  • 6244 reflections

  • 293 parameters

  • 2 restraints

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

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.40 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2816 Friedel pairs

  • Flack parameter: 0.1 (1)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯S2 0.88 (1) 2.09 (3) 2.867 (4) 147 (5)

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 (2,4-dichlorophenylamino)-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 at 283 K, and then 1-bromoundecane (0.1 mol) was added drop wise 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 crystal (31% yield; mp.350 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 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 C26H37Cl2NOS2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
n-Undecanyl 2-(2,4-dichloroanilino)-4,4-dimethyl-6-oxocyclohex-1-enecarbodithioate top
Crystal data top
C26H37Cl2NOS2F(000) = 1096
Mr = 514.59Dx = 1.256 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 2890 reflections
a = 14.6145 (4) Åθ = 2.6–19.4°
b = 31.378 (1) ŵ = 0.41 mm1
c = 5.9332 (2) ÅT = 100 K
V = 2720.8 (2) Å3Plate, yellow
Z = 40.30 × 0.20 × 0.02 mm
Data collection top
Bruker SMART APEX
diffractometer
6244 independent reflections
Radiation source: fine-focus sealed tube4130 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.084
ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1818
Tmin = 0.665, Tmax = 0.992k = 4040
24605 measured reflectionsl = 77
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)] = 0.064H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.177 w = 1/[σ2(Fo2) + (0.09P)2 + 0.1294P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
6244 reflectionsΔρmax = 0.37 e Å3
293 parametersΔρmin = 0.40 e Å3
2 restraintsAbsolute structure: Flack (1983), 2816 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.1 (1)
Crystal data top
C26H37Cl2NOS2V = 2720.8 (2) Å3
Mr = 514.59Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 14.6145 (4) ŵ = 0.41 mm1
b = 31.378 (1) ÅT = 100 K
c = 5.9332 (2) Å0.30 × 0.20 × 0.02 mm
Data collection top
Bruker SMART APEX
diffractometer
6244 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4130 reflections with I > 2σ(I)
Tmin = 0.665, Tmax = 0.992Rint = 0.084
24605 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.064H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.177Δρmax = 0.37 e Å3
S = 1.05Δρmin = 0.40 e Å3
6244 reflectionsAbsolute structure: Flack (1983), 2816 Friedel pairs
293 parametersAbsolute structure parameter: 0.1 (1)
2 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl11.00959 (9)0.61556 (4)0.0000 (3)0.0572 (4)
Cl20.78356 (10)0.56460 (5)0.6578 (3)0.0792 (6)
S11.14467 (7)0.80008 (4)0.2529 (2)0.0428 (3)
S20.96442 (7)0.76693 (4)0.1253 (2)0.0438 (3)
O11.2659 (2)0.77730 (11)0.0313 (7)0.0582 (11)
N10.9918 (2)0.70203 (12)0.2082 (7)0.0368 (9)
H10.961 (3)0.7208 (14)0.128 (9)0.072 (19)*
C11.2230 (3)0.75073 (15)0.1403 (9)0.0398 (11)
C21.2713 (3)0.72670 (17)0.3218 (8)0.0461 (13)
H2A1.26940.74390.46160.055*
H2B1.33630.72350.27820.055*
C31.2328 (3)0.68261 (15)0.3737 (8)0.0388 (10)
C41.1304 (3)0.68848 (14)0.4192 (7)0.0354 (10)
H4A1.10190.66010.43820.042*
H4B1.12270.70420.56260.042*
C51.0805 (3)0.71211 (13)0.2352 (8)0.0342 (9)
C61.1242 (3)0.74336 (14)0.0975 (8)0.0358 (10)
C71.2483 (3)0.65146 (16)0.1819 (8)0.0461 (12)
H7A1.31380.64960.14900.069*
H7B1.21560.66140.04750.069*
H7C1.22530.62330.22520.069*
C81.2777 (3)0.6654 (2)0.5899 (8)0.0539 (14)
H8A1.34320.66090.56360.081*
H8B1.24900.63830.63150.081*
H8C1.26940.68600.71230.081*
C91.0777 (3)0.76748 (13)0.0756 (8)0.0345 (10)
C101.0630 (3)0.82146 (14)0.4492 (8)0.0410 (11)
H10A1.03620.79820.54070.049*
H10B1.01300.83600.36720.049*
C111.1127 (3)0.85293 (15)0.6007 (9)0.0440 (11)
H11A1.14250.87490.50590.053*
H11B1.16130.83770.68470.053*
C121.0492 (3)0.87471 (15)0.7678 (10)0.0478 (12)
H12A1.02840.85350.88010.057*
H12B0.99460.88520.68640.057*
C131.0937 (4)0.91173 (17)0.8903 (10)0.0566 (14)
H13A1.10360.93510.78070.068*
H13B1.15460.90240.94430.068*
C141.0409 (4)0.9295 (2)1.0893 (11)0.0703 (17)
H14A1.07270.95521.14570.084*
H14B1.04090.90811.21190.084*
C150.9460 (5)0.9406 (2)1.0351 (12)0.0747 (18)
H15A0.94570.96360.92090.090*
H15B0.91520.91550.96870.090*
C160.8908 (4)0.9558 (2)1.2488 (13)0.0769 (19)
H16A0.91450.98381.29890.092*
H16B0.90010.93521.37300.092*
C170.7924 (5)0.9595 (2)1.2005 (12)0.0746 (19)
H17A0.78380.98071.07860.090*
H17B0.77000.93171.14410.090*
C180.7344 (4)0.9726 (2)1.4016 (13)0.078 (2)
H18A0.74751.00281.43960.093*
H18B0.75120.95491.53340.093*
C190.6346 (5)0.9677 (3)1.3545 (15)0.097 (2)
H19A0.62220.93741.31900.117*
H19B0.61910.98461.21910.117*
C200.5735 (5)0.9809 (3)1.5409 (15)0.103 (3)
H20A0.50990.97441.50120.155*
H20B0.59020.96551.67850.155*
H20C0.57991.01161.56630.155*
C210.9445 (3)0.66872 (13)0.3226 (8)0.0363 (11)
C220.9440 (3)0.62774 (14)0.2343 (10)0.0420 (11)
C230.8932 (3)0.59622 (15)0.3351 (9)0.0448 (12)
H230.89150.56850.27120.054*
C240.8448 (3)0.60482 (16)0.5284 (11)0.0511 (14)
C250.8451 (3)0.64514 (16)0.6211 (10)0.0491 (13)
H250.81170.65090.75500.059*
C260.8953 (3)0.67727 (14)0.5153 (9)0.0408 (11)
H260.89550.70520.57670.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0577 (8)0.0573 (8)0.0566 (7)0.0050 (6)0.0064 (7)0.0103 (7)
Cl20.0463 (8)0.0621 (9)0.1293 (15)0.0022 (7)0.0212 (9)0.0387 (10)
S10.0261 (5)0.0416 (6)0.0608 (7)0.0032 (5)0.0118 (6)0.0043 (6)
S20.0229 (5)0.0495 (7)0.0592 (7)0.0022 (5)0.0030 (6)0.0071 (6)
O10.0199 (15)0.059 (2)0.095 (3)0.0036 (14)0.0063 (18)0.017 (2)
N10.0203 (16)0.039 (2)0.051 (3)0.0035 (15)0.0032 (17)0.0007 (19)
C10.0199 (19)0.045 (2)0.054 (3)0.0005 (19)0.012 (2)0.003 (2)
C20.022 (2)0.068 (3)0.048 (3)0.007 (2)0.0052 (19)0.000 (2)
C30.026 (2)0.061 (3)0.030 (2)0.0031 (19)0.001 (2)0.005 (2)
C40.026 (2)0.049 (3)0.031 (2)0.0050 (18)0.0022 (17)0.003 (2)
C50.0222 (18)0.038 (2)0.043 (2)0.0000 (16)0.004 (2)0.012 (2)
C60.0210 (19)0.039 (2)0.048 (3)0.0015 (17)0.0090 (19)0.007 (2)
C70.036 (2)0.059 (3)0.043 (3)0.013 (2)0.002 (2)0.006 (2)
C80.034 (3)0.098 (4)0.030 (2)0.017 (3)0.004 (2)0.014 (3)
C90.0211 (19)0.036 (2)0.047 (3)0.0005 (17)0.0100 (18)0.007 (2)
C100.033 (2)0.039 (2)0.051 (3)0.0016 (19)0.008 (2)0.001 (2)
C110.040 (2)0.043 (3)0.050 (3)0.001 (2)0.013 (2)0.000 (2)
C120.048 (3)0.047 (3)0.049 (3)0.005 (2)0.001 (3)0.002 (2)
C130.050 (3)0.057 (3)0.063 (3)0.003 (3)0.010 (3)0.008 (3)
C140.070 (4)0.070 (4)0.071 (4)0.003 (3)0.005 (4)0.008 (3)
C150.079 (5)0.069 (4)0.076 (4)0.001 (3)0.002 (4)0.009 (3)
C160.069 (4)0.071 (4)0.091 (5)0.004 (3)0.015 (4)0.026 (4)
C170.078 (5)0.059 (4)0.087 (5)0.006 (3)0.012 (4)0.007 (3)
C180.063 (4)0.079 (4)0.091 (5)0.005 (3)0.015 (4)0.031 (4)
C190.089 (5)0.104 (5)0.099 (6)0.018 (4)0.015 (5)0.026 (5)
C200.070 (4)0.125 (6)0.116 (7)0.027 (4)0.029 (5)0.004 (6)
C210.0192 (19)0.039 (2)0.050 (3)0.0032 (17)0.0009 (18)0.003 (2)
C220.027 (2)0.040 (2)0.059 (3)0.0040 (18)0.008 (2)0.005 (2)
C230.028 (2)0.037 (3)0.069 (4)0.0013 (19)0.009 (2)0.002 (2)
C240.022 (2)0.048 (3)0.084 (4)0.0005 (19)0.002 (2)0.022 (3)
C250.026 (2)0.057 (3)0.065 (3)0.007 (2)0.017 (2)0.011 (3)
C260.028 (2)0.036 (2)0.058 (3)0.0047 (18)0.013 (2)0.000 (2)
Geometric parameters (Å, º) top
Cl1—C221.731 (5)C12—H12A0.9900
Cl2—C241.727 (5)C12—H12B0.9900
S1—C91.764 (4)C13—C141.516 (8)
S1—C101.797 (5)C13—H13A0.9900
S2—C91.682 (4)C13—H13B0.9900
O1—C11.228 (5)C14—C151.466 (9)
N1—C51.343 (5)C14—H14A0.9900
N1—C211.425 (6)C14—H14B0.9900
N1—H10.882 (10)C15—C161.577 (9)
C1—C61.483 (6)C15—H15A0.9900
C1—C21.492 (7)C15—H15B0.9900
C2—C31.524 (7)C16—C171.470 (8)
C2—H2A0.9900C16—H16A0.9900
C2—H2B0.9900C16—H16B0.9900
C3—C71.517 (7)C17—C181.521 (9)
C3—C41.533 (6)C17—H17A0.9900
C3—C81.539 (7)C17—H17B0.9900
C4—C51.508 (6)C18—C191.494 (9)
C4—H4A0.9900C18—H18A0.9900
C4—H4B0.9900C18—H18B0.9900
C5—C61.427 (6)C19—C201.480 (10)
C6—C91.446 (7)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—C261.377 (7)
C8—H8C0.9800C21—C221.388 (6)
C10—C111.520 (6)C22—C231.374 (7)
C10—H10A0.9900C23—C241.374 (8)
C10—H10B0.9900C23—H230.9500
C11—C121.520 (7)C24—C251.380 (7)
C11—H11A0.9900C25—C261.395 (6)
C11—H11B0.9900C25—H250.9500
C12—C131.517 (7)C26—H260.9500
C9—S1—C10103.6 (2)C14—C13—H13A108.3
C5—N1—C21125.7 (4)C12—C13—H13A108.3
C5—N1—H1114 (4)C14—C13—H13B108.3
C21—N1—H1120 (4)C12—C13—H13B108.3
O1—C1—C6120.9 (4)H13A—C13—H13B107.4
O1—C1—C2118.8 (4)C15—C14—C13113.5 (5)
C6—C1—C2120.3 (4)C15—C14—H14A108.9
C1—C2—C3115.5 (4)C13—C14—H14A108.9
C1—C2—H2A108.4C15—C14—H14B108.9
C3—C2—H2A108.4C13—C14—H14B108.9
C1—C2—H2B108.4H14A—C14—H14B107.7
C3—C2—H2B108.4C14—C15—C16112.3 (6)
H2A—C2—H2B107.5C14—C15—H15A109.1
C7—C3—C2112.2 (4)C16—C15—H15A109.1
C7—C3—C4110.8 (4)C14—C15—H15B109.1
C2—C3—C4106.7 (4)C16—C15—H15B109.1
C7—C3—C8109.6 (4)H15A—C15—H15B107.9
C2—C3—C8109.3 (4)C17—C16—C15111.5 (6)
C4—C3—C8108.1 (4)C17—C16—H16A109.3
C5—C4—C3113.8 (4)C15—C16—H16A109.3
C5—C4—H4A108.8C17—C16—H16B109.3
C3—C4—H4A108.8C15—C16—H16B109.3
C5—C4—H4B108.8H16A—C16—H16B108.0
C3—C4—H4B108.8C16—C17—C18114.4 (6)
H4A—C4—H4B107.7C16—C17—H17A108.7
N1—C5—C6121.7 (4)C18—C17—H17A108.7
N1—C5—C4115.9 (4)C16—C17—H17B108.7
C6—C5—C4122.4 (4)C18—C17—H17B108.7
C5—C6—C9123.7 (4)H17A—C17—H17B107.6
C5—C6—C1116.4 (4)C19—C18—C17111.7 (6)
C9—C6—C1119.8 (4)C19—C18—H18A109.3
C3—C7—H7A109.5C17—C18—H18A109.3
C3—C7—H7B109.5C19—C18—H18B109.3
H7A—C7—H7B109.5C17—C18—H18B109.3
C3—C7—H7C109.5H18A—C18—H18B107.9
H7A—C7—H7C109.5C20—C19—C18114.8 (7)
H7B—C7—H7C109.5C20—C19—H19A108.6
C3—C8—H8A109.5C18—C19—H19A108.6
C3—C8—H8B109.5C20—C19—H19B108.6
H8A—C8—H8B109.5C18—C19—H19B108.6
C3—C8—H8C109.5H19A—C19—H19B107.5
H8A—C8—H8C109.5C19—C20—H20A109.5
H8B—C8—H8C109.5C19—C20—H20B109.5
C6—C9—S2125.6 (3)H20A—C20—H20B109.5
C6—C9—S1117.8 (3)C19—C20—H20C109.5
S2—C9—S1116.6 (3)H20A—C20—H20C109.5
C11—C10—S1108.0 (3)H20B—C20—H20C109.5
C11—C10—H10A110.1C26—C21—C22119.4 (4)
S1—C10—H10A110.1C26—C21—N1120.4 (4)
C11—C10—H10B110.1C22—C21—N1120.1 (4)
S1—C10—H10B110.1C23—C22—C21120.3 (5)
H10A—C10—H10B108.4C23—C22—Cl1119.3 (4)
C12—C11—C10112.7 (4)C21—C22—Cl1120.3 (4)
C12—C11—H11A109.0C22—C23—C24120.0 (5)
C10—C11—H11A109.0C22—C23—H23120.0
C12—C11—H11B109.0C24—C23—H23120.0
C10—C11—H11B109.0C23—C24—C25120.7 (4)
H11A—C11—H11B107.8C23—C24—Cl2119.6 (4)
C13—C12—C11113.3 (4)C25—C24—Cl2119.7 (4)
C13—C12—H12A108.9C24—C25—C26119.0 (5)
C11—C12—H12A108.9C24—C25—H25120.5
C13—C12—H12B108.9C26—C25—H25120.5
C11—C12—H12B108.9C21—C26—C25120.5 (4)
H12A—C12—H12B107.7C21—C26—H26119.8
C14—C13—C12115.8 (5)C25—C26—H26119.8
O1—C1—C2—C3152.8 (5)C9—S1—C10—C11175.8 (3)
C6—C1—C2—C328.9 (6)S1—C10—C11—C12177.4 (3)
C1—C2—C3—C768.3 (5)C10—C11—C12—C13169.5 (4)
C1—C2—C3—C453.1 (5)C11—C12—C13—C14168.9 (5)
C1—C2—C3—C8169.8 (4)C12—C13—C14—C1552.6 (7)
C7—C3—C4—C569.6 (5)C13—C14—C15—C16175.9 (5)
C2—C3—C4—C552.8 (5)C14—C15—C16—C17169.8 (6)
C8—C3—C4—C5170.2 (4)C15—C16—C17—C18178.1 (6)
C21—N1—C5—C6173.9 (4)C16—C17—C18—C19169.0 (6)
C21—N1—C5—C46.2 (6)C17—C18—C19—C20178.5 (7)
C3—C4—C5—N1150.6 (4)C5—N1—C21—C2695.2 (5)
C3—C4—C5—C629.5 (6)C5—N1—C21—C2287.9 (6)
N1—C5—C6—C91.9 (7)C26—C21—C22—C231.6 (7)
C4—C5—C6—C9178.1 (4)N1—C21—C22—C23175.4 (4)
N1—C5—C6—C1178.4 (4)C26—C21—C22—Cl1176.9 (3)
C4—C5—C6—C11.6 (6)N1—C21—C22—Cl16.1 (6)
O1—C1—C6—C5179.3 (4)C21—C22—C23—C242.1 (7)
C2—C1—C6—C51.0 (6)Cl1—C22—C23—C24176.4 (4)
O1—C1—C6—C90.4 (7)C22—C23—C24—C251.2 (7)
C2—C1—C6—C9178.7 (4)C22—C23—C24—Cl2178.3 (4)
C5—C6—C9—S26.9 (6)C23—C24—C25—C260.1 (7)
C1—C6—C9—S2172.8 (4)Cl2—C24—C25—C26179.7 (4)
C5—C6—C9—S1172.5 (3)C22—C21—C26—C250.2 (7)
C1—C6—C9—S17.8 (5)N1—C21—C26—C25176.8 (4)
C10—S1—C9—C6176.9 (3)C24—C25—C26—C210.7 (7)
C10—S1—C9—S22.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S20.88 (1)2.09 (3)2.867 (4)147 (5)

Experimental details

Crystal data
Chemical formulaC26H37Cl2NOS2
Mr514.59
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)100
a, b, c (Å)14.6145 (4), 31.378 (1), 5.9332 (2)
V3)2720.8 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.41
Crystal size (mm)0.30 × 0.20 × 0.02
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.665, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
24605, 6244, 4130
Rint0.084
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.177, 1.05
No. of reflections6244
No. of parameters293
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.37, 0.40
Absolute structureFlack (1983), 2816 Friedel pairs
Absolute structure parameter0.1 (1)

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···S20.88 (1)2.09 (3)2.867 (4)147 (5)
 

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 citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science 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

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