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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2892.
Published online 2009 October 28. doi:  10.1107/S1600536809041762
PMCID: PMC2971401

N-Cyclohexyl-N-methylbenzene­sulfonamide

Abstract

The title compound, C13H19NO2S, was synthesized by the reaction of N-cyclo­hexyl­amine­benzene­sulfonamide and methyl iodide. The crystal packing is stabilized by weak inter­molecular C—H(...)O hydrogen bonds.

Related literature

Compounds containing cyclo­hexyl­amine have been reported to be activators of dopamine receptors in the central nervous system, see: Hacksell et al. (1981 [triangle]). For related structures, see: Arshad et al. (2008 [triangle], 2009 [triangle]).

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Object name is e-65-o2892-scheme1.jpg

Experimental

Crystal data

  • C13H19NO2S
  • M r = 253.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2892-efi1.jpg
  • a = 9.2729 (5) Å
  • b = 12.1182 (7) Å
  • c = 12.5801 (7) Å
  • β = 109.103 (2)°
  • V = 1335.79 (13) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 296 K
  • 0.28 × 0.12 × 0.09 mm

Data collection

  • Bruker APEXII CCD detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.938, T max = 0.979
  • 12741 measured reflections
  • 2489 independent reflections
  • 1864 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.113
  • S = 1.08
  • 2489 reflections
  • 155 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [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: SHELXL97 and DIAMOND (Brandenburg, 2005 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809041762/bt5092sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041762/bt5092Isup2.hkl

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

supplementary crystallographic information

Comment

Sulfonamide compounds have gained much importance due to their therapeutic applications. The compound containing cyclohexylamine has been reported to be an activator of dopamine receptors in the CNS (Hacksell et al., 1981). The title compound is a sulfonamide derivative of cyclohexylamine in continuation to our previous work (Arshad et al., 2008; Arshad et al., 2009).

The molecular structure of the title compound (I) is shown in Fig. 1. The mean plane of the benzene ring and that of the four essentially planar C atoms (C8, C9, C11, C12. Maximum deviation, 0.0132 Å) of the chair-form cyclohexyl ring have a dihedral angle of 24.26 (9)°. Furthermore, there are intermolecular C—H···O hydrogen bonds between the aromatic H atom (H2) and one sulfonamide O atom (O2i, symmetric code: see table 1) of neighboring molecules that contribute to the three-dimensional packing (Fig. 2).

Experimental

Sodium hydride (0.88 mmol) was taken in a round bottom flask and washed with n-hexane so as to remove the mineral oil dispersant. A solution of N-cyclohexylamine benzene sulfonamide (0.43 mmol) in 5 ml of N,N dimethyl formamide was added. The mixture was stirred for half an hour at room temperature. Then, methyl iodide (0.86 mmol) was added and stirring was continued for about 3 hrs until the complete consumption of sulfonamide. The reaction was monitored by TLC. After the completion of the reaction the contents were transferred into the distilled water ice. The product precipitated and was separated by filtration and recrystallized from methanol. The melting point of the product was observed to be 353 K uncorrected.

Refinement

All H atoms were placed in calculated positions and refined using a riding model [C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic H atoms; C—H = 0.98 Å and Uiso(H) = 1.2Ueq(C) for tertiary CH; C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2; C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for the methyl H atoms]. The final difference Fourier map had a highest peak at 0.71 Å from atom C1 and a deepest hole at 0.71 A Å from atom S1, but were otherwise featureless.

Figures

Fig. 1.
The molecular structure of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Diagram showing the intermolecular hydrogen bonds (indicated by pink dashed lines).

Crystal data

C13H19NO2SF(000) = 544
Mr = 253.35Dx = 1.260 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3617 reflections
a = 9.2729 (5) Åθ = 2.3–25.5°
b = 12.1182 (7) ŵ = 0.23 mm1
c = 12.5801 (7) ÅT = 296 K
β = 109.103 (2)°Block, colourless
V = 1335.79 (13) Å30.28 × 0.12 × 0.09 mm
Z = 4

Data collection

Bruker APEXII CCD detector diffractometer2489 independent reflections
Radiation source: fine-focus sealed tube1864 reflections with I > 2σ(I)
graphiteRint = 0.030
phi and ω scansθmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −10→11
Tmin = 0.938, Tmax = 0.979k = −14→14
12741 measured reflectionsl = −13→15

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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0559P)2 + 0.2086P] where P = (Fo2 + 2Fc2)/3
2489 reflections(Δ/σ)max < 0.001
155 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = −0.25 e Å3

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
C10.67239 (19)0.36402 (15)0.21562 (15)0.0443 (5)
C20.6576 (2)0.33212 (18)0.31729 (17)0.0556 (5)
H20.71030.27100.35560.067*
C30.5644 (2)0.3918 (2)0.3605 (2)0.0694 (7)
H30.55520.37170.42940.083*
C40.4849 (3)0.4804 (2)0.3038 (2)0.0738 (7)
H40.42000.51920.33320.089*
C50.5005 (3)0.51236 (19)0.2034 (2)0.0732 (7)
H50.44670.57310.16520.088*
C60.5951 (2)0.45494 (17)0.15921 (18)0.0568 (5)
H60.60700.47720.09180.068*
C71.0474 (2)0.29629 (15)0.33830 (14)0.0424 (4)
H70.98360.24010.35700.051*
C81.0716 (2)0.38752 (18)0.42469 (16)0.0568 (5)
H8A0.97390.41940.42030.068*
H8B1.13380.44520.40840.068*
C91.1495 (2)0.3434 (2)0.54232 (16)0.0632 (6)
H9A1.16780.40370.59580.076*
H9B1.08290.29070.56100.076*
C101.2988 (2)0.2885 (2)0.55192 (17)0.0651 (6)
H10A1.34160.25630.62620.078*
H10B1.37010.34340.54300.078*
C111.2786 (3)0.1995 (2)0.46425 (18)0.0679 (7)
H11A1.22030.13920.48050.082*
H11B1.37800.17100.46820.082*
C121.1976 (2)0.24159 (18)0.34615 (16)0.0546 (5)
H12A1.17870.18050.29360.065*
H12B1.26250.29430.32550.065*
C131.0145 (3)0.4353 (2)0.18252 (19)0.0719 (7)
H13A0.98570.49650.21970.108*
H13B0.96590.44210.10270.108*
H13C1.12330.43500.19960.108*
N10.96659 (17)0.33232 (13)0.22141 (13)0.0485 (4)
O10.78750 (17)0.17730 (12)0.18902 (14)0.0710 (5)
O20.75416 (18)0.32058 (15)0.04381 (11)0.0769 (5)
S10.79429 (6)0.29004 (4)0.15969 (4)0.0523 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0369 (9)0.0421 (11)0.0442 (10)−0.0061 (8)0.0002 (7)−0.0009 (8)
C20.0458 (11)0.0601 (14)0.0563 (12)−0.0031 (10)0.0104 (9)0.0119 (10)
C30.0505 (12)0.0910 (19)0.0690 (15)−0.0087 (13)0.0227 (11)−0.0028 (13)
C40.0447 (12)0.0776 (18)0.098 (2)−0.0046 (12)0.0213 (13)−0.0252 (15)
C50.0569 (14)0.0515 (14)0.098 (2)0.0069 (11)0.0078 (13)0.0027 (13)
C60.0513 (12)0.0506 (13)0.0579 (12)0.0002 (10)0.0033 (10)0.0078 (10)
C70.0397 (10)0.0442 (11)0.0410 (10)−0.0014 (8)0.0101 (8)0.0003 (8)
C80.0558 (12)0.0591 (13)0.0535 (12)0.0128 (10)0.0151 (9)−0.0100 (10)
C90.0655 (14)0.0758 (16)0.0468 (12)0.0075 (11)0.0163 (10)−0.0124 (10)
C100.0573 (13)0.0805 (17)0.0477 (12)0.0090 (11)0.0039 (10)−0.0097 (11)
C110.0618 (14)0.0700 (16)0.0583 (13)0.0212 (11)0.0009 (10)−0.0093 (11)
C120.0519 (12)0.0567 (13)0.0507 (12)0.0091 (9)0.0108 (9)−0.0131 (9)
C130.0738 (15)0.0693 (16)0.0675 (15)−0.0071 (12)0.0162 (12)0.0176 (12)
N10.0454 (9)0.0507 (10)0.0462 (9)−0.0010 (7)0.0108 (7)0.0024 (7)
O10.0658 (10)0.0425 (9)0.0905 (11)−0.0052 (7)0.0064 (8)−0.0131 (8)
O20.0797 (11)0.1027 (13)0.0379 (8)0.0063 (9)0.0050 (7)−0.0119 (8)
S10.0513 (3)0.0512 (3)0.0449 (3)−0.0004 (2)0.0027 (2)−0.0090 (2)

Geometric parameters (Å, °)

C1—C61.378 (3)C9—C101.505 (3)
C1—C21.385 (3)C9—H9A0.9700
C1—S11.760 (2)C9—H9B0.9700
C2—C31.369 (3)C10—C111.509 (3)
C2—H20.9300C10—H10A0.9700
C3—C41.364 (3)C10—H10B0.9700
C3—H30.9300C11—C121.517 (3)
C4—C51.374 (4)C11—H11A0.9700
C4—H40.9300C11—H11B0.9700
C5—C61.372 (3)C12—H12A0.9700
C5—H50.9300C12—H12B0.9700
C6—H60.9300C13—N11.462 (3)
C7—N11.481 (2)C13—H13A0.9600
C7—C81.515 (3)C13—H13B0.9600
C7—C121.516 (3)C13—H13C0.9600
C7—H70.9800N1—S11.6144 (16)
C8—C91.516 (3)O1—S11.4218 (16)
C8—H8A0.9700O2—S11.4302 (15)
C8—H8B0.9700
C6—C1—C2120.5 (2)H9A—C9—H9B108.0
C6—C1—S1119.68 (16)C9—C10—C11111.51 (18)
C2—C1—S1119.84 (15)C9—C10—H10A109.3
C3—C2—C1119.1 (2)C11—C10—H10A109.3
C3—C2—H2120.5C9—C10—H10B109.3
C1—C2—H2120.5C11—C10—H10B109.3
C4—C3—C2120.8 (2)H10A—C10—H10B108.0
C4—C3—H3119.6C10—C11—C12112.27 (18)
C2—C3—H3119.6C10—C11—H11A109.2
C3—C4—C5120.1 (2)C12—C11—H11A109.1
C3—C4—H4120.0C10—C11—H11B109.1
C5—C4—H4120.0C12—C11—H11B109.1
C6—C5—C4120.2 (2)H11A—C11—H11B107.9
C6—C5—H5119.9C11—C12—C7111.14 (17)
C4—C5—H5119.9C11—C12—H12A109.4
C5—C6—C1119.4 (2)C7—C12—H12A109.4
C5—C6—H6120.3C11—C12—H12B109.4
C1—C6—H6120.3C7—C12—H12B109.4
N1—C7—C8113.90 (15)H12A—C12—H12B108.0
N1—C7—C12110.43 (15)N1—C13—H13A109.5
C8—C7—C12110.80 (15)N1—C13—H13B109.5
N1—C7—H7107.1H13A—C13—H13B109.5
C8—C7—H7107.1N1—C13—H13C109.5
C12—C7—H7107.1H13A—C13—H13C109.5
C7—C8—C9110.76 (17)H13B—C13—H13C109.5
C7—C8—H8A109.5C13—N1—C7118.27 (15)
C9—C8—H8A109.5C13—N1—S1118.12 (13)
C7—C8—H8B109.5C7—N1—S1118.92 (12)
C9—C8—H8B109.5O1—S1—O2119.63 (10)
H8A—C8—H8B108.1O1—S1—N1107.52 (9)
C10—C9—C8111.50 (17)O2—S1—N1107.13 (10)
C10—C9—H9A109.3O1—S1—C1107.27 (10)
C8—C9—H9A109.3O2—S1—C1106.79 (9)
C10—C9—H9B109.3N1—S1—C1108.06 (8)
C8—C9—H9B109.3

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.932.523.268 (3)137

Symmetry codes: (i) x, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5092).

References

  • Arshad, M. N., Tahir, M. N., Khan, I. U., Ahmad, E. & Shafiq, M. (2008). Acta Cryst. E64, o2380. [PMC free article] [PubMed]
  • Arshad, M. N., Tahir, M. N., Khan, I. U., Shafiq, M. & Ahmad, S. (2009). Acta Cryst. E65, o940. [PMC free article] [PubMed]
  • Brandenburg, K. (2005). DIAMOND Crystal Impact GbR. Bonn, Germany.
  • Bruker (2005). APEX2, SAINT, and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Hacksell, U., Arvidsson, L.-E., Svensson, U., Nilsson, J. L. G., Sanchez, D., Wikstroem, H., Lindberg, P., Hjorth, S. & Carlsson, A. (1981). J. Med. Chem. 24, 1475–1482. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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