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Acta Cryst. (2012). E68, o1050    [ doi:10.1107/S1600536812010239 ]

4a-Methyl-2,3,4,4a-tetrahydro-1H-carbazole-6-sulfonamide

A. O. Al-Youbi, A. M. Asiri, H. M. Faidallah, S. W. Ng and E. R. T. Tiekink

Abstract top

In the title molecule, C13H16N2O2S, the nine non-H atoms comprising the indole residue are approximately coplanar (r.m.s. deviation = 0.031 Å). The partially saturated ring adopts a chair conformation. One amine H forms an intermolecular N-H...O hydrogen bond to a sulfonamide O atom, while the other amine H form is connected to the indole N atom of an adjacent molecule via an N-H...N hydrogen bond, resulting in a three-dimensional architecture.

Comment top

Sulphonamides related to the title compound, 4b-methyl-5,6,7,8-tetrahydro-4H-carbazole-3-sulfonic acid amide (I), are known to possess biological activity (Al-Saadi et al., 2008). In continuation of structural studies of these systems (Asiri et al., 2011; Asiri et al., 2012), the crystal and molecular structure of (I) is reported herein.

In (I), Fig. 1, the partially saturated ring adopts the conformation of a chair. The nine non-carbon atoms of the indole residue are co-planar, having a r.m.s. deviation of 0.031 Å. With reference to this plane, the C1—C6 ring and the amino group lie to one side, with the methyl group and one sulphonamide-O atom being orientated to the other.

Strong hydrogen bonding interactions dominate the crystal packing. Thus, one amino-H forms a hydrogen bond to the sulphonamide-O1 atom while the others forms a hydrogen bond to the indole-N atom, Table 1. The result is a three-dimensional architecture, Fig. 2.

Related literature top

For background to the biological applications of related sulfonamides, see: Al-Saadi et al. (2008). For related structures, see: Asiri et al. (2011, 2012).

Experimental top

1-Methylcyclohexanone (1.1 g, 10 mmol) in ethanol was refluxed with p-sulfamylphenylhydrazine (2.2 g, 10 mmol) for 1 h. The reaction mixture was cooled and the precipitated solid product was collected by filtration, washed with ethanol, dried and recrystallized from ethanol. Yield: 78%.

Refinement top

Carbon-bound H-atoms were placed in calculated positions [C—H = 0.95 to 0.99 Å, Uiso(H) = 1.2Ueq(C)] and were included in the refinement in the riding model approximation. The amino H-atoms were located in a difference Fourier map, and were refined with a distance restraint of N—H = 0.88±0.01 Å; their Uiso values were refined.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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 DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. A view in projection down the a axis of the unit-cell contents of (I). The N—H···O and N—H···N interactions are shown as orange and blue dashed lines, respectively.
4a-Methyl-2,3,4,4a-tetrahydro-1H-carbazole-6-sulfonamide top
Crystal data top
C13H16N2O2SF(000) = 560
Mr = 264.34Dx = 1.363 Mg m−3
Monoclinic, P21/nMelting point = 513–514 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 9.3694 (5) ÅCell parameters from 2450 reflections
b = 10.4051 (5) Åθ = 2.4–27.5°
c = 13.5937 (8) ŵ = 0.25 mm−1
β = 103.516 (6)°T = 100 K
V = 1288.54 (12) Å3Prism, light-brown
Z = 40.25 × 0.20 × 0.10 mm
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector		2959 independent reflections
Radiation source: SuperNova (Mo) X-ray Source2364 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.030
Detector resolution: 10.4041 pixels mm-1θmax = 27.6°, θmin = 2.4°
ω scanh = −8→12
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)		k = −10→13
Tmin = 0.941, Tmax = 0.976l = −17→17
5426 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0503P)2 + 0.7098P]
where P = (Fo2 + 2Fc2)/3
2959 reflections(Δ/σ)max = 0.001
171 parametersΔρmax = 0.79 e Å−3
0 restraintsΔρmin = −0.48 e Å−3
Crystal data top
C13H16N2O2SV = 1288.54 (12) Å3
Mr = 264.34Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.3694 (5) ŵ = 0.25 mm−1
b = 10.4051 (5) ÅT = 100 K
c = 13.5937 (8) Å0.25 × 0.20 × 0.10 mm
β = 103.516 (6)°
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector		2959 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)		2364 reflections with I > 2σ(I)
Tmin = 0.941, Tmax = 0.976Rint = 0.030
5426 measured reflectionsθmax = 27.6°
Refinement top
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121Δρmax = 0.79 e Å−3
S = 1.05Δρmin = −0.48 e Å−3
2959 reflectionsAbsolute structure: ?
171 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.72173 (5)0.36862 (5)0.76427 (4)0.01546 (15)
O10.76980 (15)0.24573 (13)0.73458 (11)0.0199 (3)
N20.8396 (2)0.47419 (18)0.74549 (15)0.0183 (4)
N10.17508 (18)0.53036 (16)0.47626 (13)0.0174 (4)
O20.70440 (16)0.38463 (14)0.86604 (11)0.0226 (4)
C10.1424 (2)0.63100 (19)0.52284 (16)0.0170 (4)
C20.0292 (2)0.7272 (2)0.47752 (16)0.0228 (5)
H2A−0.04520.73410.51840.027*
H2B−0.02090.70110.40800.027*
C30.1071 (3)0.8567 (2)0.47558 (17)0.0230 (5)
H3A0.17170.85160.42760.028*
H3B0.03290.92440.45130.028*
C40.1988 (2)0.8935 (2)0.58062 (16)0.0223 (5)
H4A0.24840.97660.57620.027*
H4B0.13320.90450.62750.027*
C50.3141 (2)0.79111 (19)0.62255 (16)0.0186 (4)
H5A0.36760.81580.69170.022*
H5B0.38590.78670.57960.022*
C60.2435 (2)0.65700 (19)0.62602 (15)0.0164 (4)
C70.1608 (2)0.6485 (2)0.71120 (17)0.0235 (5)
H7A0.11740.56280.71120.035*
H7B0.08280.71340.70010.035*
H7C0.22930.66400.77650.035*
C80.3498 (2)0.54740 (18)0.62982 (15)0.0143 (4)
C90.4757 (2)0.51408 (18)0.70010 (15)0.0147 (4)
H90.50940.56330.75990.018*
C100.5525 (2)0.40494 (18)0.68035 (15)0.0143 (4)
C110.5027 (2)0.32996 (19)0.59393 (15)0.0176 (4)
H110.55540.25520.58340.021*
C120.3755 (2)0.36502 (18)0.52309 (16)0.0168 (4)
H120.34020.31510.46390.020*
C130.3022 (2)0.47451 (19)0.54154 (15)0.0157 (4)
H10.847 (3)0.474 (2)0.683 (2)0.032 (7)*
H20.816 (3)0.549 (3)0.764 (2)0.030 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0175 (3)0.0139 (3)0.0143 (3)0.00338 (19)0.00238 (19)0.00179 (18)
O10.0226 (8)0.0133 (7)0.0235 (8)0.0049 (6)0.0049 (6)0.0014 (6)
N20.0192 (9)0.0167 (9)0.0180 (10)−0.0003 (7)0.0025 (7)−0.0014 (7)
N10.0159 (8)0.0189 (8)0.0160 (9)0.0011 (7)0.0009 (7)−0.0010 (7)
O20.0280 (8)0.0262 (8)0.0137 (8)0.0064 (7)0.0048 (6)0.0038 (6)
C10.0135 (9)0.0201 (10)0.0175 (10)−0.0014 (8)0.0037 (8)−0.0002 (8)
C20.0194 (10)0.0282 (11)0.0179 (11)0.0073 (9)−0.0014 (8)−0.0030 (9)
C30.0285 (12)0.0216 (11)0.0185 (11)0.0103 (9)0.0043 (9)0.0015 (8)
C40.0269 (11)0.0200 (10)0.0196 (11)0.0057 (9)0.0050 (9)−0.0009 (9)
C50.0226 (11)0.0159 (10)0.0172 (10)0.0030 (9)0.0046 (8)−0.0006 (8)
C60.0176 (10)0.0180 (10)0.0136 (10)0.0039 (8)0.0038 (8)0.0016 (8)
C70.0232 (11)0.0281 (11)0.0208 (11)0.0069 (9)0.0084 (9)0.0025 (9)
C80.0160 (9)0.0138 (9)0.0145 (10)−0.0001 (8)0.0061 (8)0.0006 (7)
C90.0178 (10)0.0148 (9)0.0120 (9)−0.0006 (8)0.0043 (8)−0.0007 (7)
C100.0142 (9)0.0146 (9)0.0144 (10)0.0012 (8)0.0040 (7)0.0035 (8)
C110.0208 (10)0.0143 (9)0.0191 (11)0.0007 (8)0.0078 (8)−0.0011 (8)
C120.0198 (10)0.0153 (10)0.0155 (10)−0.0036 (8)0.0043 (8)−0.0032 (8)
C130.0150 (9)0.0179 (10)0.0145 (10)−0.0024 (8)0.0038 (8)0.0005 (8)
Geometric parameters (Å, º) top
S1—O21.4398 (15)C4—H4B0.9900
S1—O11.4442 (14)C5—C61.549 (3)
S1—N21.6197 (19)C5—H5A0.9900
S1—C101.764 (2)C5—H5B0.9900
N2—H10.86 (3)C6—C81.507 (3)
N2—H20.86 (3)C6—C71.539 (3)
N1—C11.297 (3)C7—H7A0.9800
N1—C131.432 (3)C7—H7B0.9800
C1—C21.484 (3)C7—H7C0.9800
C1—C61.522 (3)C8—C91.377 (3)
C2—C31.536 (3)C8—C131.401 (3)
C2—H2A0.9900C9—C101.403 (3)
C2—H2B0.9900C9—H90.9500
C3—C41.533 (3)C10—C111.396 (3)
C3—H3A0.9900C11—C121.395 (3)
C3—H3B0.9900C11—H110.9500
C4—C51.529 (3)C12—C131.383 (3)
C4—H4A0.9900C12—H120.9500
O2—S1—O1118.92 (9)C4—C5—H5B109.3
O2—S1—N2107.89 (10)C6—C5—H5B109.3
O1—S1—N2106.72 (10)H5A—C5—H5B107.9
O2—S1—C10108.08 (9)C8—C6—C199.28 (16)
O1—S1—C10107.50 (9)C8—C6—C7112.08 (16)
N2—S1—C10107.21 (9)C1—C6—C7111.62 (17)
S1—N2—H1111.6 (17)C8—C6—C5113.55 (16)
S1—N2—H2109.5 (17)C1—C6—C5108.06 (16)
H1—N2—H2112 (2)C7—C6—C5111.58 (17)
C1—N1—C13106.40 (17)C6—C7—H7A109.5
N1—C1—C2124.71 (19)C6—C7—H7B109.5
N1—C1—C6115.23 (18)H7A—C7—H7B109.5
C2—C1—C6119.57 (18)C6—C7—H7C109.5
C1—C2—C3107.61 (17)H7A—C7—H7C109.5
C1—C2—H2A110.2H7B—C7—H7C109.5
C3—C2—H2A110.2C9—C8—C13120.48 (18)
C1—C2—H2B110.2C9—C8—C6131.77 (18)
C3—C2—H2B110.2C13—C8—C6107.74 (17)
H2A—C2—H2B108.5C8—C9—C10117.72 (18)
C4—C3—C2111.61 (18)C8—C9—H9121.1
C4—C3—H3A109.3C10—C9—H9121.1
C2—C3—H3A109.3C11—C10—C9121.85 (18)
C4—C3—H3B109.3C11—C10—S1119.82 (15)
C2—C3—H3B109.3C9—C10—S1118.23 (15)
H3A—C3—H3B108.0C12—C11—C10119.89 (18)
C5—C4—C3111.52 (17)C12—C11—H11120.1
C5—C4—H4A109.3C10—C11—H11120.1
C3—C4—H4A109.3C13—C12—C11118.07 (19)
C5—C4—H4B109.3C13—C12—H12121.0
C3—C4—H4B109.3C11—C12—H12121.0
H4A—C4—H4B108.0C12—C13—C8121.94 (18)
C4—C5—C6111.71 (17)C12—C13—N1126.75 (18)
C4—C5—H5A109.3C8—C13—N1111.29 (17)
C6—C5—H5A109.3
C13—N1—C1—C2172.04 (19)C13—C8—C9—C10−0.6 (3)
C13—N1—C1—C60.1 (2)C6—C8—C9—C10−179.19 (19)
N1—C1—C2—C3−117.4 (2)C8—C9—C10—C11−1.4 (3)
C6—C1—C2—C354.2 (2)C8—C9—C10—S1174.85 (15)
C1—C2—C3—C4−54.0 (2)O2—S1—C10—C11−139.60 (16)
C2—C3—C4—C558.2 (2)O1—S1—C10—C11−10.09 (19)
C3—C4—C5—C6−56.1 (2)N2—S1—C10—C11104.33 (17)
N1—C1—C6—C81.3 (2)O2—S1—C10—C944.03 (18)
C2—C1—C6—C8−171.03 (18)O1—S1—C10—C9173.54 (15)
N1—C1—C6—C7−117.0 (2)N2—S1—C10—C9−72.03 (17)
C2—C1—C6—C770.6 (2)C9—C10—C11—C121.8 (3)
N1—C1—C6—C5119.95 (19)S1—C10—C11—C12−174.46 (15)
C2—C1—C6—C5−52.4 (2)C10—C11—C12—C130.0 (3)
C4—C5—C6—C8159.10 (17)C11—C12—C13—C8−2.0 (3)
C4—C5—C6—C150.0 (2)C11—C12—C13—N1176.45 (19)
C4—C5—C6—C7−73.1 (2)C9—C8—C13—C122.3 (3)
C1—C6—C8—C9176.5 (2)C6—C8—C13—C12−178.76 (18)
C7—C6—C8—C9−65.5 (3)C9—C8—C13—N1−176.32 (18)
C5—C6—C8—C962.1 (3)C6—C8—C13—N12.6 (2)
C1—C6—C8—C13−2.2 (2)C1—N1—C13—C12179.7 (2)
C7—C6—C8—C13115.73 (19)C1—N1—C13—C8−1.7 (2)
C5—C6—C8—C13−116.70 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···N1i0.86 (3)2.13 (3)2.986 (3)170 (2)
N2—H2···O1ii0.86 (3)2.20 (3)3.039 (2)164 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, y+1/2, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···N1i0.86 (3)2.13 (3)2.986 (3)170 (2)
N2—H2···O1ii0.86 (3)2.20 (3)3.039 (2)164 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, y+1/2, −z+3/2.
Acknowledgements top

The authors are grateful to the Center of Excellence for Advanced Materials Research and the Chemistry Department at King Abdulaziz University for providing the research facilities. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

references
References top

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.

Al-Saadi, M. S., Rostom, S. A. F. & Faidallah, H. M. (2008). Arch. Pharm. Chem. Life Sci. 341, 181–190.

Asiri, A. M., Al-Youbi, A. O., Faidallah, H. M., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o2424.

Asiri, A. M., Faidallah, H. M., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o762–o763.

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.