organic compounds
N-Cyclohexyl-N-ethyl-4-methylbenzenesulfonamide
aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore, Pakistan, and bDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
*Correspondence e-mail: iukhan.gcu@hotmail.com
The title compound, C15H23NO2S, contains cyclohexyl and ethyl substituents on the sulfonamide N atom and the cyclohexyl ring adopts a classic chair conformation. The dihedral angle between the benzene ring plane and the mean plane through the six atoms of the cyclohexyl ring is 59.92 (6)°. In the C—H⋯O hydrogen bonds link molecules into sheets extending in the bc plane.
Related literature
For ring conformations, see: Cremer & Pople (1975). For related structures, see: Arshad et al. (2008, 2009); Khan et al. (2009); Gowda et al. (2007a,b,c).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004)), PLATON (Spek, 2009) and publCIF (Westrip, 2009).
Supporting information
10.1107/S1600536809052593/bt5132sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809052593/bt5132Isup2.hkl
A mixture of N-cyclohexyl-4-methyl benzene sulfonamide (1.089 g, 4.3 mmol), sodium hydride (0.21 g, 8.6 mmol) and N, N-dimethylformamide (10 ml) was stirred at room temperature for half an hour followed by addition of ethyl iodode (1.32 g, 8.6 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.
All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, Uiso=1.2Ueq (C) for aromatic 0.98 Å, Uiso = 1.2Ueq (C) for CH, 0.97 Å, Uiso = 1.2Ueq (C) for CH2, 0.96 Å, Uiso = 1.5Ueq (C) for CH3 atoms.
The 1 0 0 reflection was identified as being obscured by the beamstop and was omitted.
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2009).C15H23NO2S | F(000) = 608 |
Mr = 281.40 | Dx = 1.238 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3495 reflections |
a = 12.2269 (5) Å | θ = 2.5–25.6° |
b = 7.5818 (3) Å | µ = 0.21 mm−1 |
c = 16.3045 (6) Å | T = 296 K |
β = 92.495 (2)° | Needle, white |
V = 1510.03 (10) Å3 | 0.43 × 0.32 × 0.15 mm |
Z = 4 |
Bruker APEXII CCD area-detector diffractometer | 3714 independent reflections |
Radiation source: fine-focus sealed tube | 2251 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
ϕ and ω scans | θmax = 28.3°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −16→15 |
Tmin = 0.914, Tmax = 0.969 | k = −10→9 |
16676 measured reflections | l = −19→21 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.048P)2 + 0.3506P] where P = (Fo2 + 2Fc2)/3 |
3713 reflections | (Δ/σ)max = 0.001 |
174 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C15H23NO2S | V = 1510.03 (10) Å3 |
Mr = 281.40 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.2269 (5) Å | µ = 0.21 mm−1 |
b = 7.5818 (3) Å | T = 296 K |
c = 16.3045 (6) Å | 0.43 × 0.32 × 0.15 mm |
β = 92.495 (2)° |
Bruker APEXII CCD area-detector diffractometer | 3714 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 2251 reflections with I > 2σ(I) |
Tmin = 0.914, Tmax = 0.969 | Rint = 0.040 |
16676 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.23 e Å−3 |
3713 reflections | Δρmin = −0.25 e Å−3 |
174 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.22960 (5) | 1.10442 (7) | 0.56680 (3) | 0.05930 (19) | |
O1 | 0.14930 (14) | 1.1507 (2) | 0.50392 (9) | 0.0866 (5) | |
O2 | 0.32184 (13) | 1.21640 (19) | 0.58303 (10) | 0.0784 (5) | |
N1 | 0.27372 (13) | 0.9101 (2) | 0.54440 (9) | 0.0549 (4) | |
C1 | 0.16215 (14) | 1.0870 (2) | 0.66002 (11) | 0.0451 (4) | |
C2 | 0.21516 (14) | 1.1373 (2) | 0.73271 (11) | 0.0511 (5) | |
H2 | 0.2856 | 1.1835 | 0.7326 | 0.061* | |
C3 | 0.16309 (15) | 1.1186 (3) | 0.80559 (12) | 0.0528 (5) | |
H3 | 0.1994 | 1.1519 | 0.8544 | 0.063* | |
C4 | 0.05847 (15) | 1.0517 (2) | 0.80760 (11) | 0.0491 (5) | |
C5 | 0.00638 (16) | 1.0042 (3) | 0.73394 (13) | 0.0571 (5) | |
H5 | −0.0645 | 0.9598 | 0.7341 | 0.069* | |
C6 | 0.05660 (16) | 1.0209 (3) | 0.66051 (12) | 0.0555 (5) | |
H6 | 0.0201 | 0.9881 | 0.6117 | 0.067* | |
C7 | 0.36213 (15) | 0.8297 (2) | 0.59696 (11) | 0.0494 (5) | |
H7 | 0.3938 | 0.9237 | 0.6317 | 0.059* | |
C8 | 0.45338 (16) | 0.7582 (3) | 0.54568 (12) | 0.0576 (5) | |
H8A | 0.4245 | 0.6660 | 0.5096 | 0.069* | |
H8B | 0.4808 | 0.8521 | 0.5118 | 0.069* | |
C9 | 0.54647 (16) | 0.6847 (3) | 0.59987 (14) | 0.0671 (6) | |
H9A | 0.6019 | 0.6358 | 0.5657 | 0.081* | |
H9B | 0.5797 | 0.7793 | 0.6323 | 0.081* | |
C10 | 0.50692 (17) | 0.5438 (3) | 0.65621 (13) | 0.0642 (6) | |
H10A | 0.5673 | 0.5044 | 0.6922 | 0.077* | |
H10B | 0.4811 | 0.4435 | 0.6239 | 0.077* | |
C11 | 0.4154 (2) | 0.6108 (3) | 0.70741 (13) | 0.0697 (6) | |
H11A | 0.4437 | 0.7014 | 0.7446 | 0.084* | |
H11B | 0.3883 | 0.5148 | 0.7402 | 0.084* | |
C12 | 0.32174 (16) | 0.6864 (3) | 0.65394 (12) | 0.0606 (5) | |
H12A | 0.2670 | 0.7355 | 0.6887 | 0.073* | |
H12B | 0.2876 | 0.5926 | 0.6214 | 0.073* | |
C13 | 0.00216 (18) | 1.0322 (3) | 0.88731 (13) | 0.0723 (6) | |
H13A | 0.0434 | 1.0933 | 0.9300 | 0.108* | |
H13B | −0.0027 | 0.9095 | 0.9011 | 0.108* | |
H13C | −0.0701 | 1.0815 | 0.8817 | 0.108* | |
C14 | 0.21331 (17) | 0.8024 (3) | 0.48246 (12) | 0.0608 (5) | |
H14A | 0.1357 | 0.8263 | 0.4855 | 0.073* | |
H14B | 0.2249 | 0.6787 | 0.4953 | 0.073* | |
C15 | 0.2469 (2) | 0.8363 (3) | 0.39659 (13) | 0.0820 (7) | |
H15A | 0.2338 | 0.9578 | 0.3828 | 0.123* | |
H15B | 0.2050 | 0.7624 | 0.3592 | 0.123* | |
H15C | 0.3233 | 0.8104 | 0.3927 | 0.123* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0778 (4) | 0.0485 (3) | 0.0529 (3) | 0.0114 (3) | 0.0175 (2) | 0.0068 (2) |
O1 | 0.1182 (13) | 0.0855 (12) | 0.0565 (9) | 0.0423 (10) | 0.0071 (9) | 0.0196 (8) |
O2 | 0.0959 (11) | 0.0491 (9) | 0.0935 (11) | −0.0132 (8) | 0.0419 (9) | −0.0031 (8) |
N1 | 0.0682 (10) | 0.0513 (10) | 0.0455 (9) | 0.0081 (8) | 0.0054 (7) | −0.0054 (8) |
C1 | 0.0487 (10) | 0.0398 (10) | 0.0470 (10) | 0.0075 (8) | 0.0052 (8) | 0.0001 (8) |
C2 | 0.0410 (10) | 0.0532 (12) | 0.0591 (12) | −0.0008 (8) | 0.0027 (9) | −0.0036 (9) |
C3 | 0.0498 (11) | 0.0590 (12) | 0.0493 (11) | 0.0003 (9) | −0.0015 (8) | −0.0077 (9) |
C4 | 0.0537 (11) | 0.0404 (10) | 0.0537 (11) | 0.0041 (8) | 0.0078 (9) | −0.0022 (9) |
C5 | 0.0451 (11) | 0.0574 (13) | 0.0692 (14) | −0.0064 (9) | 0.0069 (9) | −0.0074 (10) |
C6 | 0.0544 (12) | 0.0569 (12) | 0.0545 (12) | −0.0010 (10) | −0.0049 (9) | −0.0104 (10) |
C7 | 0.0611 (11) | 0.0441 (10) | 0.0433 (10) | 0.0015 (9) | 0.0046 (8) | −0.0062 (8) |
C8 | 0.0590 (12) | 0.0559 (12) | 0.0593 (12) | −0.0029 (10) | 0.0164 (9) | 0.0029 (10) |
C9 | 0.0551 (12) | 0.0620 (14) | 0.0845 (16) | −0.0010 (11) | 0.0058 (11) | −0.0003 (12) |
C10 | 0.0640 (13) | 0.0517 (12) | 0.0760 (15) | 0.0047 (10) | −0.0062 (11) | −0.0023 (11) |
C11 | 0.0958 (16) | 0.0593 (14) | 0.0543 (12) | 0.0046 (12) | 0.0053 (11) | 0.0072 (11) |
C12 | 0.0674 (13) | 0.0616 (13) | 0.0543 (12) | 0.0078 (11) | 0.0207 (10) | 0.0053 (10) |
C13 | 0.0765 (15) | 0.0772 (16) | 0.0649 (14) | −0.0025 (12) | 0.0229 (11) | −0.0008 (12) |
C14 | 0.0638 (12) | 0.0607 (13) | 0.0576 (12) | −0.0026 (10) | −0.0001 (10) | −0.0015 (10) |
C15 | 0.0992 (18) | 0.0938 (19) | 0.0525 (13) | −0.0011 (15) | −0.0013 (12) | −0.0099 (13) |
S1—O2 | 1.4272 (16) | C8—H8B | 0.9700 |
S1—O1 | 1.4320 (16) | C9—C10 | 1.502 (3) |
S1—N1 | 1.6160 (17) | C9—H9A | 0.9700 |
S1—C1 | 1.7654 (18) | C9—H9B | 0.9700 |
N1—C14 | 1.472 (2) | C10—C11 | 1.513 (3) |
N1—C7 | 1.481 (2) | C10—H10A | 0.9700 |
C1—C2 | 1.380 (2) | C10—H10B | 0.9700 |
C1—C6 | 1.385 (3) | C11—C12 | 1.521 (3) |
C2—C3 | 1.380 (3) | C11—H11A | 0.9700 |
C2—H2 | 0.9300 | C11—H11B | 0.9700 |
C3—C4 | 1.378 (3) | C12—H12A | 0.9700 |
C3—H3 | 0.9300 | C12—H12B | 0.9700 |
C4—C5 | 1.383 (3) | C13—H13A | 0.9600 |
C4—C13 | 1.504 (3) | C13—H13B | 0.9600 |
C5—C6 | 1.375 (3) | C13—H13C | 0.9600 |
C5—H5 | 0.9300 | C14—C15 | 1.498 (3) |
C6—H6 | 0.9300 | C14—H14A | 0.9700 |
C7—C8 | 1.523 (3) | C14—H14B | 0.9700 |
C7—C12 | 1.525 (3) | C15—H15A | 0.9600 |
C7—H7 | 0.9800 | C15—H15B | 0.9600 |
C8—C9 | 1.517 (3) | C15—H15C | 0.9600 |
C8—H8A | 0.9700 | ||
O2—S1—O1 | 119.90 (11) | C8—C9—H9A | 109.4 |
O2—S1—N1 | 108.38 (9) | C10—C9—H9B | 109.4 |
O1—S1—N1 | 106.68 (9) | C8—C9—H9B | 109.4 |
O2—S1—C1 | 106.25 (9) | H9A—C9—H9B | 108.0 |
O1—S1—C1 | 107.65 (9) | C9—C10—C11 | 111.34 (18) |
N1—S1—C1 | 107.42 (8) | C9—C10—H10A | 109.4 |
C14—N1—C7 | 120.00 (16) | C11—C10—H10A | 109.4 |
C14—N1—S1 | 119.89 (13) | C9—C10—H10B | 109.4 |
C7—N1—S1 | 119.14 (12) | C11—C10—H10B | 109.4 |
C2—C1—C6 | 119.88 (17) | H10A—C10—H10B | 108.0 |
C2—C1—S1 | 119.95 (14) | C10—C11—C12 | 111.52 (17) |
C6—C1—S1 | 120.16 (15) | C10—C11—H11A | 109.3 |
C3—C2—C1 | 119.63 (17) | C12—C11—H11A | 109.3 |
C3—C2—H2 | 120.2 | C10—C11—H11B | 109.3 |
C1—C2—H2 | 120.2 | C12—C11—H11B | 109.3 |
C2—C3—C4 | 121.47 (17) | H11A—C11—H11B | 108.0 |
C2—C3—H3 | 119.3 | C11—C12—C7 | 111.20 (17) |
C4—C3—H3 | 119.3 | C11—C12—H12A | 109.4 |
C3—C4—C5 | 117.93 (17) | C7—C12—H12A | 109.4 |
C3—C4—C13 | 121.15 (18) | C11—C12—H12B | 109.4 |
C5—C4—C13 | 120.93 (18) | C7—C12—H12B | 109.4 |
C6—C5—C4 | 121.74 (18) | H12A—C12—H12B | 108.0 |
C6—C5—H5 | 119.1 | C4—C13—H13A | 109.5 |
C4—C5—H5 | 119.1 | C4—C13—H13B | 109.5 |
C5—C6—C1 | 119.34 (18) | H13A—C13—H13B | 109.5 |
C5—C6—H6 | 120.3 | C4—C13—H13C | 109.5 |
C1—C6—H6 | 120.3 | H13A—C13—H13C | 109.5 |
N1—C7—C8 | 111.26 (15) | H13B—C13—H13C | 109.5 |
N1—C7—C12 | 113.46 (16) | N1—C14—C15 | 113.33 (17) |
C8—C7—C12 | 110.21 (16) | N1—C14—H14A | 108.9 |
N1—C7—H7 | 107.2 | C15—C14—H14A | 108.9 |
C8—C7—H7 | 107.2 | N1—C14—H14B | 108.9 |
C12—C7—H7 | 107.2 | C15—C14—H14B | 108.9 |
C9—C8—C7 | 111.12 (16) | H14A—C14—H14B | 107.7 |
C9—C8—H8A | 109.4 | C14—C15—H15A | 109.5 |
C7—C8—H8A | 109.4 | C14—C15—H15B | 109.5 |
C9—C8—H8B | 109.4 | H15A—C15—H15B | 109.5 |
C7—C8—H8B | 109.4 | C14—C15—H15C | 109.5 |
H8A—C8—H8B | 108.0 | H15A—C15—H15C | 109.5 |
C10—C9—C8 | 111.37 (17) | H15B—C15—H15C | 109.5 |
C10—C9—H9A | 109.4 | ||
O2—S1—N1—C14 | −144.40 (15) | C13—C4—C5—C6 | −179.92 (19) |
O1—S1—N1—C14 | −14.01 (17) | C4—C5—C6—C1 | 0.0 (3) |
C1—S1—N1—C14 | 101.19 (15) | C2—C1—C6—C5 | −0.8 (3) |
O2—S1—N1—C7 | 46.86 (16) | S1—C1—C6—C5 | 178.40 (15) |
O1—S1—N1—C7 | 177.24 (14) | C14—N1—C7—C8 | 60.5 (2) |
C1—S1—N1—C7 | −67.56 (15) | S1—N1—C7—C8 | −130.77 (15) |
O2—S1—C1—C2 | −15.54 (18) | C14—N1—C7—C12 | −64.5 (2) |
O1—S1—C1—C2 | −145.16 (16) | S1—N1—C7—C12 | 104.27 (17) |
N1—S1—C1—C2 | 100.29 (16) | N1—C7—C8—C9 | 177.02 (16) |
O2—S1—C1—C6 | 165.26 (15) | C12—C7—C8—C9 | −56.2 (2) |
O1—S1—C1—C6 | 35.64 (18) | C7—C8—C9—C10 | 56.7 (2) |
N1—S1—C1—C6 | −78.91 (16) | C8—C9—C10—C11 | −55.7 (2) |
C6—C1—C2—C3 | 1.0 (3) | C9—C10—C11—C12 | 55.0 (2) |
S1—C1—C2—C3 | −178.17 (14) | C10—C11—C12—C7 | −55.1 (2) |
C1—C2—C3—C4 | −0.5 (3) | N1—C7—C12—C11 | −179.00 (15) |
C2—C3—C4—C5 | −0.3 (3) | C8—C7—C12—C11 | 55.5 (2) |
C2—C3—C4—C13 | −179.85 (19) | C7—N1—C14—C15 | −103.9 (2) |
C3—C4—C5—C6 | 0.6 (3) | S1—N1—C14—C15 | 87.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···O2i | 0.97 | 2.66 | 3.530 (3) | 150 |
C13—H13A···O1ii | 0.96 | 2.60 | 3.512 (3) | 159 |
Symmetry codes: (i) x, y−1, z; (ii) x, −y+5/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H23NO2S |
Mr | 281.40 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 12.2269 (5), 7.5818 (3), 16.3045 (6) |
β (°) | 92.495 (2) |
V (Å3) | 1510.03 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.43 × 0.32 × 0.15 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.914, 0.969 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16676, 3714, 2251 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.122, 0.99 |
No. of reflections | 3713 |
No. of parameters | 174 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.25 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···O2i | 0.97 | 2.66 | 3.530 (3) | 149.5 |
C13—H13A···O1ii | 0.96 | 2.60 | 3.512 (3) | 158.5 |
Symmetry codes: (i) x, y−1, z; (ii) x, −y+5/2, z+1/2. |
Acknowledgements
The authors acknowledge the Higher Education Commission of Pakistan for providing a grant under the `Strengthening of the Materials Chemistry Laboratory' project at GC University, Lahore, Pakistan.
References
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Our group has been involved in the synthesis and crystallographic studies of sulfonamide derivatives (Arshad et al., 2009).
The title compound is a benzenesulfonamide with cyclohexyl and ethyl substituents on the sulfonamide N1 atom, Fig. 1. Bond distances in the molecule are comparable to those in similar structures (Arshad et al., 2008; Khan et al., 2009; Gowda et al., 2007a,b,c). The cyclohexyl (C7···C12) ring adopts a classic chair conformation with puckering amplitude Q = 0.567 (2) Å, θ = 178.8 (2) °, ϕ = 214 (11) ° (Cremer & Pople, 1975) and the plane through this ring is inclined at 59.92 (6) ° to that of the C1···C6 benzene ring. In the crystal structure C—H···O hydrogen bonds involving the C13–H13 bond of the methyl group and the C10–H10B bond of the cyclohexyl ring link each molecule to the O1 and O2 atoms of individual sulphonamide units forming an extended two dimensional network in the bc plane (Table 1, Fig. 2).