PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3109.
Published online 2009 November 18. doi:  10.1107/S1600536809048193
PMCID: PMC2972048

N-Benzyl-N-cyclo­hexyl-4-methyl­benzene­sulfonamide

Abstract

In the title compound, C20H25NO2S, the cyclo­hexyl ring exists in a chair form and the mean plane through all six atoms makes dihedral angles of 56.12 (9) and 55.19 (10)° with the benzene and phenyl rings, respectively. The dihedral angle between the two aromatic rings is 77.23 (7)°. A weak intra­molecular C—H(...)O interaction occurs.

Related literature

For the biological activity of sulfonamides, see: 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]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o3109-scheme1.jpg

Experimental

Crystal data

  • C20H25NO2S
  • M r = 343.47
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3109-efi1.jpg
  • a = 9.0702 (4) Å
  • b = 11.1054 (5) Å
  • c = 18.1971 (8) Å
  • V = 1832.96 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.19 mm−1
  • T = 296 K
  • 0.24 × 0.18 × 0.13 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.956, T max = 0.976
  • 11619 measured reflections
  • 4493 independent reflections
  • 2764 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.097
  • S = 0.98
  • 4493 reflections
  • 218 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.25 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1915 Friedel pairs
  • Flack parameter: 0.04 (8)

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: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809048193/is2488sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048193/is2488Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

Sulfonamides are well known as anti-inflamatory (Ratish et al., 2009), anti-microbial (Ozbek et al., 2007; Parari et al., 2008), anti HIV (Selnam et al., 2001) compounds. In continuation of our work regarding the synthesis of various sulfur containing heterocycles (Zia-ur-Rehman et al., 2009; Khan et al., 2009), the structure of N-benzyl-N-cyclohexyl-4-methyl benzene sulfonamide, (I), has been determined.

Bond lengths and bond angles of the title molecule (Fig. 1) are almost similar to those in the related molecules (Gowda et al., 2007a,b,c) and are within the normal ranges (Allen et al., 1987). The two aromatic rings as usual are essentially planar, while the cyclohexane ring is in a chair form. The dihedral angles between the two aromatic rings (C1—C6) & (C14—C19), the benzene (C1—C6) ring & the mean plane of cyclohexyl ring (C7—C12), and the phenyl (C14—C19) ring & the mean plane cyclohexyl ring (C7—C12) are 77.23 (7), 56.12 (9) and 55.19 (10)°, respectively, while the r.m.s. deviations for the (C1—C6), (C7—C12) & (C14—C19) rings are 0.0056, 0.2320 and 0.0046 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-cyclohexyl-4-methyl benzene sulfonamide (1.089 g, 4.3 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 (1.14 g, 9.0 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 a methanol solution.

Refinement

All H atoms were identified in a difference map and then were treated as riding (C—H = 0.93–0.98 Å), with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Figures

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

Crystal data

C20H25NO2SF(000) = 736
Mr = 343.47Dx = 1.245 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2246 reflections
a = 9.0702 (4) Åθ = 2.9–20.7°
b = 11.1054 (5) ŵ = 0.19 mm1
c = 18.1971 (8) ÅT = 296 K
V = 1832.96 (14) Å3Blocks, yellow
Z = 40.24 × 0.18 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer4493 independent reflections
Radiation source: fine-focus sealed tube2764 reflections with I > 2σ(I)
graphiteRint = 0.036
[var phi] and ω scansθmax = 28.3°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.956, Tmax = 0.976k = −14→7
11619 measured reflectionsl = −24→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.097w = 1/[σ2(Fo2) + (0.0397P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
4493 reflectionsΔρmax = 0.16 e Å3
218 parametersΔρmin = −0.24 e Å3
0 restraintsAbsolute structure: Flack (1983), 1915 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.04 (8)

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
S10.13668 (7)0.35270 (6)0.83512 (3)0.04431 (17)
O10.0611 (2)0.45762 (15)0.86060 (9)0.0603 (5)
O20.28860 (18)0.36124 (17)0.81433 (9)0.0604 (5)
N10.04730 (19)0.30283 (17)0.76418 (9)0.0396 (5)
C10.1256 (3)0.2456 (2)0.90607 (11)0.0386 (5)
C20.2185 (3)0.1481 (2)0.90729 (13)0.0520 (6)
H20.28720.13750.86990.062*
C30.2102 (3)0.0660 (2)0.96364 (14)0.0556 (7)
H30.2729−0.00020.96320.067*
C40.1123 (3)0.0789 (2)1.02044 (13)0.0492 (6)
C50.0189 (3)0.1763 (3)1.01803 (13)0.0634 (8)
H5−0.04980.18671.05540.076*
C60.0247 (3)0.2591 (3)0.96159 (13)0.0607 (8)
H6−0.03990.32410.96120.073*
C7−0.1161 (2)0.3031 (2)0.76700 (11)0.0404 (6)
H7−0.14440.35590.80780.049*
C8−0.1825 (2)0.1808 (2)0.78275 (15)0.0573 (7)
H8A−0.14510.15070.82920.069*
H8B−0.15390.12460.74450.069*
C9−0.3505 (3)0.1892 (3)0.78615 (16)0.0700 (8)
H9A−0.39160.10940.79330.084*
H9B−0.37900.23850.82780.084*
C10−0.4124 (3)0.2434 (3)0.71630 (16)0.0723 (9)
H10A−0.39130.19040.67520.087*
H10B−0.51860.25080.72070.087*
C11−0.3468 (3)0.3647 (3)0.70192 (14)0.0630 (8)
H11A−0.37520.41950.74090.076*
H11B−0.38520.39610.65600.076*
C12−0.1796 (2)0.3582 (3)0.69771 (13)0.0556 (7)
H12A−0.15090.31000.65560.067*
H12B−0.13980.43850.69110.067*
C130.1222 (3)0.2229 (2)0.71193 (11)0.0423 (6)
H13A0.06130.15220.70430.051*
H13B0.21430.19640.73360.051*
C140.1544 (2)0.2793 (2)0.63832 (12)0.0412 (6)
C150.2396 (3)0.3820 (2)0.63277 (14)0.0582 (8)
H150.27450.41940.67510.070*
C160.2731 (3)0.4293 (3)0.56453 (18)0.0753 (9)
H160.33110.49810.56140.090*
C170.2222 (4)0.3763 (3)0.50164 (17)0.0773 (10)
H170.24570.40820.45590.093*
C180.1365 (4)0.2759 (3)0.50727 (15)0.0756 (9)
H180.10070.23930.46490.091*
C190.1022 (3)0.2279 (2)0.57493 (14)0.0572 (7)
H190.04300.15970.57770.069*
C200.1098 (3)−0.0076 (3)1.08385 (14)0.0736 (9)
H20A0.02700.01001.11490.110*
H20B0.19930.00031.11160.110*
H20C0.1015−0.08841.06560.110*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0498 (4)0.0418 (3)0.0414 (3)−0.0050 (3)−0.0074 (3)−0.0030 (3)
O10.0852 (13)0.0385 (10)0.0573 (12)0.0057 (9)−0.0130 (9)−0.0102 (9)
O20.0487 (10)0.0769 (14)0.0555 (11)−0.0207 (10)−0.0072 (8)0.0060 (10)
N10.0385 (11)0.0467 (13)0.0337 (11)0.0014 (9)−0.0024 (8)−0.0059 (9)
C10.0404 (13)0.0399 (14)0.0353 (12)−0.0011 (12)−0.0071 (11)−0.0064 (10)
C20.0575 (15)0.0552 (16)0.0432 (15)0.0053 (15)0.0086 (11)−0.0058 (15)
C30.0648 (17)0.0481 (17)0.0538 (17)0.0098 (14)−0.0022 (14)−0.0005 (14)
C40.0535 (17)0.0530 (17)0.0413 (14)−0.0061 (14)−0.0065 (13)0.0013 (12)
C50.0583 (17)0.089 (3)0.0429 (16)0.0123 (17)0.0101 (12)0.0069 (16)
C60.0546 (17)0.078 (2)0.0499 (16)0.0238 (15)0.0055 (13)0.0068 (15)
C70.0394 (14)0.0433 (14)0.0385 (12)0.0043 (11)0.0007 (11)−0.0047 (10)
C80.0416 (16)0.0557 (19)0.0747 (19)−0.0022 (12)0.0023 (12)0.0114 (15)
C90.0506 (16)0.070 (2)0.089 (2)−0.0053 (15)0.0082 (16)0.0075 (17)
C100.0379 (16)0.104 (3)0.075 (2)0.0028 (16)−0.0055 (13)−0.010 (2)
C110.0489 (16)0.084 (2)0.0561 (16)0.0138 (17)−0.0051 (12)0.0061 (17)
C120.0495 (16)0.0620 (18)0.0552 (16)0.0061 (14)−0.0051 (11)0.0098 (16)
C130.0404 (13)0.0429 (15)0.0437 (14)0.0034 (12)0.0023 (11)−0.0019 (11)
C140.0426 (14)0.0415 (15)0.0396 (13)0.0057 (12)0.0020 (11)−0.0025 (11)
C150.0599 (18)0.062 (2)0.0528 (16)−0.0095 (15)−0.0029 (13)0.0043 (14)
C160.073 (2)0.078 (2)0.075 (2)−0.0156 (18)0.0113 (18)0.022 (2)
C170.094 (2)0.090 (3)0.0482 (19)0.011 (2)0.0187 (16)0.0196 (19)
C180.102 (2)0.079 (2)0.0459 (17)0.015 (2)0.0012 (18)−0.0021 (16)
C190.0699 (19)0.0531 (18)0.0486 (16)0.0012 (14)0.0012 (13)−0.0011 (14)
C200.093 (2)0.066 (2)0.0620 (18)−0.0067 (18)−0.0045 (16)0.0123 (16)

Geometric parameters (Å, °)

S1—O11.4291 (17)C10—C111.495 (4)
S1—O21.4321 (17)C10—H10A0.9700
S1—N11.6219 (18)C10—H10B0.9700
S1—C11.758 (2)C11—C121.520 (3)
N1—C131.467 (3)C11—H11A0.9700
N1—C71.483 (3)C11—H11B0.9700
C1—C61.371 (3)C12—H12A0.9700
C1—C21.372 (3)C12—H12B0.9700
C2—C31.374 (3)C13—C141.507 (3)
C2—H20.9300C13—H13A0.9700
C3—C41.370 (3)C13—H13B0.9700
C3—H30.9300C14—C191.372 (3)
C4—C51.374 (3)C14—C151.381 (3)
C4—C201.502 (3)C15—C161.382 (4)
C5—C61.379 (3)C15—H150.9300
C5—H50.9300C16—C171.367 (4)
C6—H60.9300C16—H160.9300
C7—C81.513 (3)C17—C181.364 (4)
C7—C121.515 (3)C17—H170.9300
C7—H70.9800C18—C191.377 (4)
C8—C91.528 (3)C18—H180.9300
C8—H8A0.9700C19—H190.9300
C8—H8B0.9700C20—H20A0.9600
C9—C101.514 (4)C20—H20B0.9600
C9—H9A0.9700C20—H20C0.9600
C9—H9B0.9700
O1—S1—O2119.55 (12)C9—C10—H10A109.5
O1—S1—N1107.27 (10)C11—C10—H10B109.5
O2—S1—N1107.05 (10)C9—C10—H10B109.5
O1—S1—C1106.61 (10)H10A—C10—H10B108.0
O2—S1—C1107.08 (11)C10—C11—C12111.3 (2)
N1—S1—C1108.96 (10)C10—C11—H11A109.4
C13—N1—C7119.09 (18)C12—C11—H11A109.4
C13—N1—S1119.41 (15)C10—C11—H11B109.4
C7—N1—S1118.11 (14)C12—C11—H11B109.4
C6—C1—C2118.9 (2)H11A—C11—H11B108.0
C6—C1—S1120.3 (2)C7—C12—C11110.9 (2)
C2—C1—S1120.71 (18)C7—C12—H12A109.5
C1—C2—C3120.1 (2)C11—C12—H12A109.5
C1—C2—H2119.9C7—C12—H12B109.5
C3—C2—H2119.9C11—C12—H12B109.5
C4—C3—C2121.9 (2)H12A—C12—H12B108.1
C4—C3—H3119.0N1—C13—C14114.46 (18)
C2—C3—H3119.0N1—C13—H13A108.6
C3—C4—C5117.2 (2)C14—C13—H13A108.6
C3—C4—C20121.5 (3)N1—C13—H13B108.6
C5—C4—C20121.3 (2)C14—C13—H13B108.6
C4—C5—C6121.7 (2)H13A—C13—H13B107.6
C4—C5—H5119.2C19—C14—C15118.4 (2)
C6—C5—H5119.2C19—C14—C13120.5 (2)
C1—C6—C5120.1 (3)C15—C14—C13121.1 (2)
C1—C6—H6120.0C14—C15—C16120.2 (3)
C5—C6—H6120.0C14—C15—H15119.9
N1—C7—C8113.73 (19)C16—C15—H15119.9
N1—C7—C12110.59 (18)C17—C16—C15121.0 (3)
C8—C7—C12111.7 (2)C17—C16—H16119.5
N1—C7—H7106.8C15—C16—H16119.5
C8—C7—H7106.8C18—C17—C16118.8 (3)
C12—C7—H7106.8C18—C17—H17120.6
C7—C8—C9110.4 (2)C16—C17—H17120.6
C7—C8—H8A109.6C17—C18—C19120.8 (3)
C9—C8—H8A109.6C17—C18—H18119.6
C7—C8—H8B109.6C19—C18—H18119.6
C9—C8—H8B109.6C14—C19—C18120.9 (3)
H8A—C8—H8B108.1C14—C19—H19119.6
C10—C9—C8111.1 (2)C18—C19—H19119.6
C10—C9—H9A109.4C4—C20—H20A109.5
C8—C9—H9A109.4C4—C20—H20B109.5
C10—C9—H9B109.4H20A—C20—H20B109.5
C8—C9—H9B109.4C4—C20—H20C109.5
H9A—C9—H9B108.0H20A—C20—H20C109.5
C11—C10—C9110.9 (2)H20B—C20—H20C109.5
C11—C10—H10A109.5
O1—S1—N1—C13159.58 (16)S1—N1—C7—C8−101.8 (2)
O2—S1—N1—C1330.12 (19)C13—N1—C7—C12−69.2 (3)
C1—S1—N1—C13−85.37 (18)S1—N1—C7—C12131.65 (18)
O1—S1—N1—C7−41.37 (19)N1—C7—C8—C9178.9 (2)
O2—S1—N1—C7−170.83 (17)C12—C7—C8—C9−55.1 (3)
C1—S1—N1—C773.68 (19)C7—C8—C9—C1055.6 (3)
O1—S1—C1—C616.6 (2)C8—C9—C10—C11−56.8 (3)
O2—S1—C1—C6145.7 (2)C9—C10—C11—C1256.8 (3)
N1—S1—C1—C6−98.9 (2)N1—C7—C12—C11−177.1 (2)
O1—S1—C1—C2−162.71 (19)C8—C7—C12—C1155.2 (3)
O2—S1—C1—C2−33.6 (2)C10—C11—C12—C7−56.0 (3)
N1—S1—C1—C281.8 (2)C7—N1—C13—C1491.6 (2)
C6—C1—C2—C3−0.3 (4)S1—N1—C13—C14−109.5 (2)
S1—C1—C2—C3179.01 (18)N1—C13—C14—C19−123.0 (2)
C1—C2—C3—C4−1.0 (4)N1—C13—C14—C1558.5 (3)
C2—C3—C4—C51.6 (4)C19—C14—C15—C16−1.3 (4)
C2—C3—C4—C20−176.6 (2)C13—C14—C15—C16177.2 (2)
C3—C4—C5—C6−1.0 (4)C14—C15—C16—C170.4 (5)
C20—C4—C5—C6177.2 (3)C15—C16—C17—C180.4 (5)
C2—C1—C6—C50.9 (4)C16—C17—C18—C19−0.4 (5)
S1—C1—C6—C5−178.4 (2)C15—C14—C19—C181.3 (4)
C4—C5—C6—C1−0.2 (4)C13—C14—C19—C18−177.2 (3)
C13—N1—C7—C857.3 (3)C17—C18—C19—C14−0.5 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7—H7···O10.982.382.903 (3)113

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2488).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Gowda, B. T., Foro, S. & Fuess, H. (2007a). Acta Cryst. E63, o2339.
  • Gowda, B. T., Foro, S. & Fuess, H. (2007b). Acta Cryst. E63, o2570.
  • Gowda, B. T., Foro, S. & Fuess, H. (2007c). Acta Cryst. E63, o2597.
  • Khan, I. U., Haider, Z., Zia-ur-Rehman, M., Arshad, M. N. & Shafiq, M. (2009). Acta Cryst. E65, o2867. [PMC free article] [PubMed]
  • Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.
  • Ozbek, N., Katircioğ lu, H., Karacan, N. & Baykal, T. (2007). Bioorg. Med. Chem 15, 5105–5109. [PubMed]
  • Parari, M. K., Panda, G., Srivastava, K. & Puri, S. K. (2008). Bioorg. Med. Chem. Lett. 18, 776–781. [PubMed]
  • Ratish, G. I., Javed, K., Ahmad, S., Bano, S., Alam, M. S., Pillai, K. K., Singh, S. & Bagchi, V. (2009). Bioorg. & Med. Chem. Lett. 19, 255–258. [PubMed]
  • Selnam, P., Chandramohan, M., Clercq, E. D., Witvrouw, M. & Pannecouque, C. (2001). Eur. J. Pharm. Sci 14, 313–316. [PubMed]
  • Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Zia-ur-Rehman, M., Choudary, J. A., Elsegood, M. R. J., Siddiqui, H. L. & Khan, K. M. (2009). Eur. J. Med. Chem 44, 1311–1316. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography