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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3053.
Published online 2009 November 11. doi:  10.1107/S1600536809046960
PMCID: PMC2971833

N-Benzyl-N-cyclo­hexyl­benzene­sulfonamide

Abstract

In the title compound, C19H23NO2S, the cyclo­hexyl ring exists in a chair form. The dihedral angle between the two terminal phenyl rings is 86.70 (6)°. No significant inter­actions are observed except for a weak intra­molecular C—H(...)O hydrogen bond.

Related literature

For the biological activity of sulfonamides, see: Innocenti et al. (2004 [triangle]); Ozbek et al. (2007 [triangle]); Parari et al. (2008 [triangle]); Ratish et al. (2009 [triangle]); Selnam et al. (2001 [triangle]); For related structures, see: Khan et al. (2009 [triangle]); Zia-ur-Rehman et al. (2009 [triangle]) Gowda et al. (2007a [triangle],b [triangle],c [triangle]). For bond length data, see: Allen et al. (1987 [triangle]).

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Object name is e-65-o3053-scheme1.jpg

Experimental

Crystal data

  • C19H23NO2S
  • M r = 329.44
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3053-efi1.jpg
  • a = 9.1996 (5) Å
  • b = 11.0406 (5) Å
  • c = 17.1897 (9) Å
  • V = 1745.94 (15) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 296 K
  • 0.39 × 0.34 × 0.28 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.928, T max = 0.948
  • 10897 measured reflections
  • 4306 independent reflections
  • 3507 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.094
  • S = 1.03
  • 4306 reflections
  • 208 parameters
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.24 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1853 Friedel pairs
  • Flack parameter: 0.03 (7)

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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: PLATON (Spek, 2009 [triangle]) and Mercury (Macrae et al., 2006 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]) and local programs.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046960/is2484sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046960/is2484Isup2.hkl

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

Acknowledgments

The authors are grateful to the Higher Education Commission of Pakistan for the financial support to purchase the diffractometer.

supplementary crystallographic information

Comment

Sulfonamides are familiar as biologically active compounds and possess anti-microbial (Ozbek et al., 2007; Parari et al., 2008), anti-inflamatory (Ratish et al., 2009), anti HIV (Selnam et al., 2001) and carbonic anhydrase inhibiton activity (Innocenti et al., 2004). In the present paper, the structure of N-cyclohexyl-N-propyl benzene sulfonamide has been determined as part of a research program involving the synthesis of various sulfur containing heterocycles (Zia-ur-Rehman et al., 2009; Khan et al., 2009).

In the molecule of (I) (Fig. 1), bond lengths and bond angles are almost similar to those in the related molecules (Gowda et al., 2007a,b,c) and are within normal ranges (Allen et al., 1987). The benzene rings are essentially planar while cyclohexane ring is in the chair form. The dihedral angles between the phenyl (C1–C6) & benzyl ring (C14–C19), the phenyl (C1–C6) ring & the mean plane of cyclohexyl ring (C7–C12), and the benzyl (C14–C19) ring & the mean plane cyclohexyl ring (C7–C12) are 86.70 (6), 42.43 (8) and 55.47 (8)°, respectively, while the r.m.s. deviation for the phenyl (C1–C6), benzyl (C14–C19) and cyclohexyl (C7–C12) rings are 0.0021, 0.0036 and 0.2365 Å, respectively. An intramolecular C—H···O hydrogen bond gives rise to a five-membered hydrogen bonded ring (Table 1).

Experimental

A mixture of N-cyclohexylbenzene sulfonamide (1 g, 0.43 mmol), sodium hydride (0.21 g, 0.88 mmol) and N, N-dimethylformamide (10 ml) was stirred at room temperature for half an hour followed by addition of benzyl chloride (0.114 g, 0.90 mmol). Stirring was continued further for a period of three hours and the contents were poured over crushed ice. Precipitated product was isolated, washed and crystallized from methanol-water mixture (50:50).

Refinement

All H atoms were identified in a difference map and then were treated as riding (C—H = 0.93 or 0.97 Å), with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of (I), with displacement ellipsoids at the 50% probability level.

Crystal data

C19H23NO2SF(000) = 704
Mr = 329.44Dx = 1.253 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3979 reflections
a = 9.1996 (5) Åθ = 2.3–21.8°
b = 11.0406 (5) ŵ = 0.20 mm1
c = 17.1897 (9) ÅT = 296 K
V = 1745.94 (15) Å3Blocks, colourless
Z = 40.39 × 0.34 × 0.28 mm

Data collection

Bruker APEXII CCD area-detector diffractometer4306 independent reflections
Radiation source: fine-focus sealed tube3507 reflections with I > 2σ(I)
graphiteRint = 0.023
[var phi] and ω scansθmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→11
Tmin = 0.928, Tmax = 0.948k = −11→14
10897 measured reflectionsl = −22→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.094w = 1/[σ2(Fo2) + (0.049P)2 + 0.1094P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4306 reflectionsΔρmax = 0.24 e Å3
208 parametersΔρmin = −0.24 e Å3
0 restraintsAbsolute structure: Flack (1983), 1853 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.03 (7)

Special details

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)

xyzUiso*/Ueq
C10.3444 (2)0.27298 (15)0.91369 (9)0.0423 (4)
C20.4528 (2)0.2866 (2)0.96899 (11)0.0596 (5)
H20.53020.23250.97090.072*
C30.4447 (3)0.3813 (2)1.02106 (13)0.0737 (7)
H30.51700.39101.05830.088*
C40.3305 (3)0.4615 (2)1.01838 (13)0.0720 (7)
H40.32520.52501.05390.086*
C50.2244 (3)0.4475 (2)0.96314 (14)0.0676 (6)
H50.14780.50230.96110.081*
C60.2295 (2)0.3532 (2)0.91061 (11)0.0542 (5)
H60.15660.34380.87360.065*
C70.61067 (18)0.20568 (15)0.77713 (10)0.0396 (4)
H70.63610.16200.82490.048*
C80.6733 (2)0.33204 (18)0.78485 (14)0.0587 (5)
H8A0.62850.37320.82860.070*
H8B0.65280.37820.73810.070*
C90.8375 (2)0.3243 (2)0.79731 (14)0.0647 (6)
H9A0.87770.40540.80020.078*
H9B0.85720.28380.84630.078*
C100.9099 (2)0.2560 (2)0.73209 (13)0.0653 (6)
H10A0.89850.30080.68390.078*
H10B1.01310.24890.74280.078*
C110.8458 (2)0.1321 (2)0.72278 (14)0.0717 (6)
H11A0.86660.08450.76890.086*
H11B0.89080.09220.67870.086*
C120.6807 (2)0.13740 (19)0.71029 (12)0.0574 (5)
H12A0.65930.17800.66160.069*
H12B0.64160.05590.70770.069*
C130.3750 (2)0.28365 (15)0.71472 (9)0.0407 (4)
H13A0.43190.35710.70880.049*
H13B0.28110.30640.73580.049*
C140.35265 (19)0.22767 (13)0.63549 (9)0.0385 (3)
C150.2610 (2)0.12964 (17)0.62532 (12)0.0556 (5)
H150.21410.09620.66810.067*
C160.2385 (3)0.0808 (2)0.55228 (14)0.0647 (6)
H160.17600.01530.54630.078*
C170.3074 (3)0.1283 (2)0.48873 (12)0.0646 (6)
H170.29170.09550.43960.077*
C180.4001 (3)0.2249 (2)0.49795 (12)0.0668 (6)
H180.44840.25680.45510.080*
C190.4216 (2)0.27463 (17)0.57071 (11)0.0535 (5)
H190.48330.34070.57620.064*
N10.44909 (16)0.20318 (12)0.77103 (8)0.0402 (3)
O10.21214 (15)0.12969 (13)0.81853 (8)0.0590 (4)
O20.43915 (17)0.05891 (11)0.88027 (8)0.0592 (4)
S10.35656 (5)0.15399 (4)0.84502 (2)0.04355 (12)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0453 (9)0.0462 (9)0.0352 (8)−0.0024 (8)0.0063 (8)0.0056 (7)
C20.0564 (12)0.0720 (13)0.0504 (11)0.0075 (11)−0.0061 (10)0.0019 (10)
C30.0780 (16)0.0892 (17)0.0539 (12)−0.0098 (14)−0.0089 (12)−0.0100 (12)
C40.0928 (19)0.0669 (13)0.0564 (12)−0.0073 (14)0.0093 (14)−0.0126 (11)
C50.0761 (15)0.0617 (13)0.0651 (14)0.0124 (12)0.0139 (12)−0.0008 (11)
C60.0508 (11)0.0621 (11)0.0495 (10)0.0073 (10)0.0009 (8)0.0008 (10)
C70.0378 (9)0.0447 (9)0.0364 (8)0.0043 (7)−0.0017 (7)0.0039 (7)
C80.0437 (11)0.0513 (10)0.0812 (14)0.0000 (9)0.0033 (10)−0.0147 (10)
C90.0432 (11)0.0695 (13)0.0815 (14)−0.0033 (10)−0.0042 (10)−0.0146 (12)
C100.0351 (10)0.0957 (17)0.0651 (13)0.0074 (11)−0.0003 (9)−0.0016 (13)
C110.0513 (12)0.0869 (16)0.0768 (14)0.0229 (13)0.0006 (11)−0.0247 (13)
C120.0501 (11)0.0611 (11)0.0610 (12)0.0101 (9)−0.0006 (9)−0.0166 (10)
C130.0418 (9)0.0388 (8)0.0416 (9)0.0036 (7)−0.0034 (7)0.0009 (7)
C140.0357 (8)0.0376 (7)0.0423 (8)0.0045 (7)−0.0080 (7)0.0032 (6)
C150.0549 (11)0.0551 (11)0.0570 (11)−0.0136 (10)−0.0014 (9)0.0008 (9)
C160.0671 (14)0.0558 (11)0.0712 (14)−0.0153 (11)−0.0111 (11)−0.0097 (11)
C170.0855 (16)0.0613 (12)0.0469 (11)0.0000 (11)−0.0204 (11)−0.0056 (10)
C180.0957 (18)0.0657 (14)0.0390 (10)−0.0094 (13)−0.0041 (10)0.0078 (10)
C190.0662 (13)0.0471 (10)0.0472 (11)−0.0115 (10)−0.0069 (9)0.0067 (9)
N10.0387 (8)0.0455 (8)0.0365 (7)0.0043 (6)−0.0002 (6)0.0043 (6)
O10.0469 (7)0.0690 (9)0.0610 (8)−0.0151 (7)0.0052 (6)−0.0039 (7)
O20.0711 (9)0.0436 (7)0.0629 (8)0.0059 (7)0.0071 (7)0.0168 (6)
S10.0449 (2)0.0415 (2)0.0442 (2)−0.0025 (2)0.0035 (2)0.00529 (19)

Geometric parameters (Å, °)

C1—C61.380 (3)C10—H10B0.9700
C1—C21.386 (3)C11—C121.535 (3)
C1—S11.7696 (18)C11—H11A0.9700
C2—C31.378 (3)C11—H11B0.9700
C2—H20.9300C12—H12A0.9700
C3—C41.375 (3)C12—H12B0.9700
C3—H30.9300C13—N11.480 (2)
C4—C51.370 (3)C13—C141.510 (2)
C4—H40.9300C13—H13A0.9700
C5—C61.379 (3)C13—H13B0.9700
C5—H50.9300C14—C191.382 (2)
C6—H60.9300C14—C151.383 (2)
C7—N11.490 (2)C15—C161.382 (3)
C7—C81.515 (3)C15—H150.9300
C7—C121.518 (2)C16—C171.368 (3)
C7—H70.9800C16—H160.9300
C8—C91.528 (3)C17—C181.374 (3)
C8—H8A0.9700C17—H170.9300
C8—H8B0.9700C18—C191.380 (3)
C9—C101.506 (3)C18—H180.9300
C9—H9A0.9700C19—H190.9300
C9—H9B0.9700N1—S11.6240 (14)
C10—C111.498 (3)O1—S11.4299 (14)
C10—H10A0.9700O2—S11.4305 (14)
C6—C1—C2120.51 (18)C12—C11—H11A109.3
C6—C1—S1119.94 (14)C10—C11—H11B109.3
C2—C1—S1119.54 (15)C12—C11—H11B109.3
C3—C2—C1119.3 (2)H11A—C11—H11B107.9
C3—C2—H2120.4C7—C12—C11109.44 (16)
C1—C2—H2120.4C7—C12—H12A109.8
C4—C3—C2120.6 (2)C11—C12—H12A109.8
C4—C3—H3119.7C7—C12—H12B109.8
C2—C3—H3119.7C11—C12—H12B109.8
C5—C4—C3119.6 (2)H12A—C12—H12B108.2
C5—C4—H4120.2N1—C13—C14114.01 (13)
C3—C4—H4120.2N1—C13—H13A108.7
C4—C5—C6121.0 (2)C14—C13—H13A108.7
C4—C5—H5119.5N1—C13—H13B108.7
C6—C5—H5119.5C14—C13—H13B108.7
C5—C6—C1119.05 (19)H13A—C13—H13B107.6
C5—C6—H6120.5C19—C14—C15118.11 (16)
C1—C6—H6120.5C19—C14—C13120.72 (15)
N1—C7—C8113.74 (14)C15—C14—C13121.17 (16)
N1—C7—C12111.15 (15)C16—C15—C14120.77 (19)
C8—C7—C12111.24 (15)C16—C15—H15119.6
N1—C7—H7106.8C14—C15—H15119.6
C8—C7—H7106.8C17—C16—C15120.4 (2)
C12—C7—H7106.8C17—C16—H16119.8
C7—C8—C9109.69 (17)C15—C16—H16119.8
C7—C8—H8A109.7C16—C17—C18119.5 (2)
C9—C8—H8A109.7C16—C17—H17120.2
C7—C8—H8B109.7C18—C17—H17120.2
C9—C8—H8B109.7C17—C18—C19120.1 (2)
H8A—C8—H8B108.2C17—C18—H18119.9
C10—C9—C8111.14 (18)C19—C18—H18119.9
C10—C9—H9A109.4C18—C19—C14121.02 (18)
C8—C9—H9A109.4C18—C19—H19119.5
C10—C9—H9B109.4C14—C19—H19119.5
C8—C9—H9B109.4C13—N1—C7119.61 (14)
H9A—C9—H9B108.0C13—N1—S1118.13 (12)
C11—C10—C9111.26 (19)C7—N1—S1118.29 (11)
C11—C10—H10A109.4O1—S1—O2119.39 (9)
C9—C10—H10A109.4O1—S1—N1107.48 (8)
C11—C10—H10B109.4O2—S1—N1107.38 (8)
C9—C10—H10B109.4O1—S1—C1107.04 (9)
H10A—C10—H10B108.0O2—S1—C1107.20 (8)
C10—C11—C12111.71 (18)N1—S1—C1107.90 (7)
C10—C11—H11A109.3
C6—C1—C2—C30.1 (3)C16—C17—C18—C19−1.0 (4)
S1—C1—C2—C3178.36 (17)C17—C18—C19—C141.0 (3)
C1—C2—C3—C40.0 (3)C15—C14—C19—C18−0.2 (3)
C2—C3—C4—C5−0.4 (4)C13—C14—C19—C18−179.12 (19)
C3—C4—C5—C60.7 (4)C14—C13—N1—C790.42 (18)
C4—C5—C6—C1−0.6 (3)C14—C13—N1—S1−112.35 (15)
C2—C1—C6—C50.3 (3)C8—C7—N1—C1349.3 (2)
S1—C1—C6—C5−178.03 (16)C12—C7—N1—C13−77.18 (18)
N1—C7—C8—C9175.43 (16)C8—C7—N1—S1−107.91 (16)
C12—C7—C8—C9−58.1 (2)C12—C7—N1—S1125.63 (14)
C7—C8—C9—C1056.9 (2)C13—N1—S1—O137.74 (14)
C8—C9—C10—C11−56.2 (3)C7—N1—S1—O1−164.73 (12)
C9—C10—C11—C1255.8 (3)C13—N1—S1—O2167.36 (12)
N1—C7—C12—C11−174.82 (17)C7—N1—S1—O2−35.11 (15)
C8—C7—C12—C1157.3 (2)C13—N1—S1—C1−77.38 (14)
C10—C11—C12—C7−56.0 (3)C7—N1—S1—C180.15 (14)
N1—C13—C14—C19−115.08 (18)C6—C1—S1—O1−25.17 (17)
N1—C13—C14—C1566.1 (2)C2—C1—S1—O1156.51 (15)
C19—C14—C15—C16−0.5 (3)C6—C1—S1—O2−154.38 (14)
C13—C14—C15—C16178.40 (19)C2—C1—S1—O227.30 (17)
C14—C15—C16—C170.5 (3)C6—C1—S1—N190.25 (16)
C15—C16—C17—C180.3 (4)C2—C1—S1—N1−88.07 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7—H7···O20.982.342.874 (2)113

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2484).

References

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