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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o599.
Published online 2009 February 25. doi:  10.1107/S1600536809006163
PMCID: PMC2968480

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

Abstract

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 [triangle]).

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Object name is e-65-0o599-scheme1.jpg

Experimental

Crystal data

  • C26H38ClNOS2
  • M r = 480.14
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o599-efi1.jpg
  • 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 [triangle]) T min = 0.892, T max = 0.969
  • 12760 measured reflections
  • 6108 independent reflections
  • 3899 reflections with I > 2σ(I)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006163/bt2878sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006163/bt2878Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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.

Figures

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.

Crystal data

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

Bruker SMART APEX diffractometer6108 independent reflections
Radiation source: fine-focus sealed tube3899 reflections with I > 2σ(I)
graphiteRint = 0.051
ω scansθmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.892, Tmax = 0.969k = −15→15
12760 measured reflectionsl = −19→19

Refinement

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 = 1.01w = 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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)
H11A0.5910−0.03680.26590.033*
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)
H13A0.6651−0.02130.10470.036*
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)
H15A0.77560.0004−0.04890.040*
H15B0.94740.1070−0.00840.040*
C160.8086 (4)0.1459 (3)−0.11602 (19)0.0305 (7)
H16A0.85720.2336−0.09900.037*
H16B0.68320.1285−0.13860.037*
C170.9041 (4)0.1038 (3)−0.19232 (19)0.0312 (7)
H17A1.03070.1254−0.17090.037*
H17B0.86030.0156−0.20690.037*
C180.8816 (4)0.1564 (3)−0.27808 (19)0.0294 (7)
H18A0.93280.2442−0.26440.035*
H18B0.75470.1396−0.29720.035*
C190.9668 (4)0.1080 (3)−0.35609 (19)0.0323 (7)
H19A1.09460.1280−0.33830.039*
H19B0.91930.0198−0.36830.039*
C200.9360 (5)0.1577 (3)−0.4419 (2)0.0421 (8)
H20A0.99420.1245−0.48990.063*
H20B0.98410.2449−0.43050.063*
H20C0.80980.1360−0.46100.063*
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)

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, °)

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—C3−165.2 (2)C10—S1—C9—C6174.7 (2)
C6—C1—C2—C315.6 (4)C10—S1—C9—S2−5.8 (2)
C1—C2—C3—C4−45.9 (3)C9—S1—C10—C11−166.72 (19)
C1—C2—C3—C8−163.9 (2)S1—C10—C11—C12−60.6 (3)
C1—C2—C3—C774.7 (3)C10—C11—C12—C13−177.9 (2)
C2—C3—C4—C555.4 (3)C11—C12—C13—C14−176.6 (3)
C8—C3—C4—C5174.0 (2)C12—C13—C14—C15177.6 (3)
C7—C3—C4—C5−65.3 (3)C13—C14—C15—C16175.3 (3)
C21—N1—C5—C6179.8 (3)C14—C15—C16—C17−178.9 (3)
C21—N1—C5—C4−0.5 (4)C15—C16—C17—C18176.8 (3)
C3—C4—C5—N1144.5 (2)C16—C17—C18—C19−176.1 (2)
C3—C4—C5—C6−35.7 (3)C17—C18—C19—C20177.6 (3)
N1—C5—C6—C92.0 (4)C5—N1—C21—C26−116.3 (3)
C4—C5—C6—C9−177.8 (2)C5—N1—C21—C2267.0 (4)
N1—C5—C6—C1−178.1 (2)C26—C21—C22—C230.8 (5)
C4—C5—C6—C12.1 (4)N1—C21—C22—C23177.4 (3)
O1—C1—C6—C5−171.1 (2)C21—C22—C23—C24−0.3 (5)
C2—C1—C6—C58.2 (4)C22—C23—C24—C250.0 (5)
O1—C1—C6—C98.8 (4)C22—C23—C24—Cl1−179.4 (3)
C2—C1—C6—C9−172.0 (2)C23—C24—C25—C26−0.1 (5)
C5—C6—C9—S24.6 (4)Cl1—C24—C25—C26179.3 (3)
C1—C6—C9—S2−175.2 (2)C22—C21—C26—C25−0.9 (5)
C5—C6—C9—S1−175.8 (2)N1—C21—C26—C25−177.6 (3)
C1—C6—C9—S14.3 (3)C24—C25—C26—C210.6 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···S20.89 (1)2.10 (2)2.873 (2)146 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2878).

References

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