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

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

doi:10.1107/S1600536812010239

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1050

doi:10.1107/S1600536812010239

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

Abdulrahman O. Al-Youbi,^a,^b ‡ Abdullah M. Asiri,^a,^b Hassan M. Faidallah,^a Seik Weng Ng ^c,^a and Edward R. T. Tiekink ^c ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, ^bThe Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah, PO Box 80203, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 6 March 2012; accepted 8 March 2012; online 14 March 2012)

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.

Related literature

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

Crystal data

C₁₃H₁₆N₂O₂S
M_r = 264.34
Monoclinic, P 2₁ /n
a = 9.3694 (5) Å
b = 10.4051 (5) Å
c = 13.5937 (8) Å
β = 103.516 (6)°
V = 1288.54 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.941, T_max = 0.976
5426 measured reflections
2959 independent reflections
2364 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.121
S = 1.05
2959 reflections
171 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯N1ⁱ	0.86 (3)	2.13 (3)	2.986 (3)	170 (2)
N2—H2⋯O1ⁱⁱ	0.86 (3)	2.20 (3)	3.039 (2)	164 (2)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812010239/xu5479sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812010239/xu5479Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812010239/xu5479Isup3.cml

checkCIF report

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%.

Structure description 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).

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

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	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

C₁₃H₁₆N₂O₂S	F(000) = 560
M_r = 264.34	D_x = 1.363 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 513–514 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.3694 (5) Å	Cell parameters from 2450 reflections
b = 10.4051 (5) Å	θ = 2.4–27.5°
c = 13.5937 (8) Å	µ = 0.25 mm⁻¹
β = 103.516 (6)°	T = 100 K
V = 1288.54 (12) Å³	Prism, light-brown
Z = 4	0.25 × 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 Source	2364 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.030
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.4°
ω scan	h = −8→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→13
T_min = 0.941, T_max = 0.976	l = −17→17
5426 measured reflections

Refinement top

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) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0503P)² + 0.7098P] where P = (F_o² + 2F_c²)/3
2959 reflections	(Δ/σ)_max = 0.001
171 parameters	Δρ_max = 0.79 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

C₁₃H₁₆N₂O₂S	V = 1288.54 (12) Å³
M_r = 264.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.3694 (5) Å	µ = 0.25 mm⁻¹
b = 10.4051 (5) Å	T = 100 K
c = 13.5937 (8) Å	0.25 × 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)
T_min = 0.941, T_max = 0.976	R_int = 0.030
5426 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.79 e Å⁻³
2959 reflections	Δρ_min = −0.48 e Å⁻³
171 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.72173 (5)	0.36862 (5)	0.76427 (4)	0.01546 (15)
O1	0.76980 (15)	0.24573 (13)	0.73458 (11)	0.0199 (3)
N2	0.8396 (2)	0.47419 (18)	0.74549 (15)	0.0183 (4)
N1	0.17508 (18)	0.53036 (16)	0.47626 (13)	0.0174 (4)
O2	0.70440 (16)	0.38463 (14)	0.86604 (11)	0.0226 (4)
C1	0.1424 (2)	0.63100 (19)	0.52284 (16)	0.0170 (4)
C2	0.0292 (2)	0.7272 (2)	0.47752 (16)	0.0228 (5)
H2A	−0.0452	0.7341	0.5184	0.027*
H2B	−0.0209	0.7011	0.4080	0.027*
C3	0.1071 (3)	0.8567 (2)	0.47558 (17)	0.0230 (5)
H3A	0.1717	0.8516	0.4276	0.028*
H3B	0.0329	0.9244	0.4513	0.028*
C4	0.1988 (2)	0.8935 (2)	0.58062 (16)	0.0223 (5)
H4A	0.2484	0.9766	0.5762	0.027*
H4B	0.1332	0.9045	0.6275	0.027*
C5	0.3141 (2)	0.79111 (19)	0.62255 (16)	0.0186 (4)
H5A	0.3676	0.8158	0.6917	0.022*
H5B	0.3859	0.7867	0.5796	0.022*
C6	0.2435 (2)	0.65700 (19)	0.62602 (15)	0.0164 (4)
C7	0.1608 (2)	0.6485 (2)	0.71120 (17)	0.0235 (5)
H7A	0.1174	0.5628	0.7112	0.035*
H7B	0.0828	0.7134	0.7001	0.035*
H7C	0.2293	0.6640	0.7765	0.035*
C8	0.3498 (2)	0.54740 (18)	0.62982 (15)	0.0143 (4)
C9	0.4757 (2)	0.51408 (18)	0.70010 (15)	0.0147 (4)
H9	0.5094	0.5633	0.7599	0.018*
C10	0.5525 (2)	0.40494 (18)	0.68035 (15)	0.0143 (4)
C11	0.5027 (2)	0.32996 (19)	0.59393 (15)	0.0176 (4)
H11	0.5554	0.2552	0.5834	0.021*
C12	0.3755 (2)	0.36502 (18)	0.52309 (16)	0.0168 (4)
H12	0.3402	0.3151	0.4639	0.020*
C13	0.3022 (2)	0.47451 (19)	0.54154 (15)	0.0157 (4)
H1	0.847 (3)	0.474 (2)	0.683 (2)	0.032 (7)*
H2	0.816 (3)	0.549 (3)	0.764 (2)	0.030 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0175 (3)	0.0139 (3)	0.0143 (3)	0.00338 (19)	0.00238 (19)	0.00179 (18)
O1	0.0226 (8)	0.0133 (7)	0.0235 (8)	0.0049 (6)	0.0049 (6)	0.0014 (6)
N2	0.0192 (9)	0.0167 (9)	0.0180 (10)	−0.0003 (7)	0.0025 (7)	−0.0014 (7)
N1	0.0159 (8)	0.0189 (8)	0.0160 (9)	0.0011 (7)	0.0009 (7)	−0.0010 (7)
O2	0.0280 (8)	0.0262 (8)	0.0137 (8)	0.0064 (7)	0.0048 (6)	0.0038 (6)
C1	0.0135 (9)	0.0201 (10)	0.0175 (10)	−0.0014 (8)	0.0037 (8)	−0.0002 (8)
C2	0.0194 (10)	0.0282 (11)	0.0179 (11)	0.0073 (9)	−0.0014 (8)	−0.0030 (9)
C3	0.0285 (12)	0.0216 (11)	0.0185 (11)	0.0103 (9)	0.0043 (9)	0.0015 (8)
C4	0.0269 (11)	0.0200 (10)	0.0196 (11)	0.0057 (9)	0.0050 (9)	−0.0009 (9)
C5	0.0226 (11)	0.0159 (10)	0.0172 (10)	0.0030 (9)	0.0046 (8)	−0.0006 (8)
C6	0.0176 (10)	0.0180 (10)	0.0136 (10)	0.0039 (8)	0.0038 (8)	0.0016 (8)
C7	0.0232 (11)	0.0281 (11)	0.0208 (11)	0.0069 (9)	0.0084 (9)	0.0025 (9)
C8	0.0160 (9)	0.0138 (9)	0.0145 (10)	−0.0001 (8)	0.0061 (8)	0.0006 (7)
C9	0.0178 (10)	0.0148 (9)	0.0120 (9)	−0.0006 (8)	0.0043 (8)	−0.0007 (7)
C10	0.0142 (9)	0.0146 (9)	0.0144 (10)	0.0012 (8)	0.0040 (7)	0.0035 (8)
C11	0.0208 (10)	0.0143 (9)	0.0191 (11)	0.0007 (8)	0.0078 (8)	−0.0011 (8)
C12	0.0198 (10)	0.0153 (10)	0.0155 (10)	−0.0036 (8)	0.0043 (8)	−0.0032 (8)
C13	0.0150 (9)	0.0179 (10)	0.0145 (10)	−0.0024 (8)	0.0038 (8)	0.0005 (8)

Geometric parameters (Å, º) top

S1—O2	1.4398 (15)	C4—H4B	0.9900
S1—O1	1.4442 (14)	C5—C6	1.549 (3)
S1—N2	1.6197 (19)	C5—H5A	0.9900
S1—C10	1.764 (2)	C5—H5B	0.9900
N2—H1	0.86 (3)	C6—C8	1.507 (3)
N2—H2	0.86 (3)	C6—C7	1.539 (3)
N1—C1	1.297 (3)	C7—H7A	0.9800
N1—C13	1.432 (3)	C7—H7B	0.9800
C1—C2	1.484 (3)	C7—H7C	0.9800
C1—C6	1.522 (3)	C8—C9	1.377 (3)
C2—C3	1.536 (3)	C8—C13	1.401 (3)
C2—H2A	0.9900	C9—C10	1.403 (3)
C2—H2B	0.9900	C9—H9	0.9500
C3—C4	1.533 (3)	C10—C11	1.396 (3)
C3—H3A	0.9900	C11—C12	1.395 (3)
C3—H3B	0.9900	C11—H11	0.9500
C4—C5	1.529 (3)	C12—C13	1.383 (3)
C4—H4A	0.9900	C12—H12	0.9500

O2—S1—O1	118.92 (9)	C4—C5—H5B	109.3
O2—S1—N2	107.89 (10)	C6—C5—H5B	109.3
O1—S1—N2	106.72 (10)	H5A—C5—H5B	107.9
O2—S1—C10	108.08 (9)	C8—C6—C1	99.28 (16)
O1—S1—C10	107.50 (9)	C8—C6—C7	112.08 (16)
N2—S1—C10	107.21 (9)	C1—C6—C7	111.62 (17)
S1—N2—H1	111.6 (17)	C8—C6—C5	113.55 (16)
S1—N2—H2	109.5 (17)	C1—C6—C5	108.06 (16)
H1—N2—H2	112 (2)	C7—C6—C5	111.58 (17)
C1—N1—C13	106.40 (17)	C6—C7—H7A	109.5
N1—C1—C2	124.71 (19)	C6—C7—H7B	109.5
N1—C1—C6	115.23 (18)	H7A—C7—H7B	109.5
C2—C1—C6	119.57 (18)	C6—C7—H7C	109.5
C1—C2—C3	107.61 (17)	H7A—C7—H7C	109.5
C1—C2—H2A	110.2	H7B—C7—H7C	109.5
C3—C2—H2A	110.2	C9—C8—C13	120.48 (18)
C1—C2—H2B	110.2	C9—C8—C6	131.77 (18)
C3—C2—H2B	110.2	C13—C8—C6	107.74 (17)
H2A—C2—H2B	108.5	C8—C9—C10	117.72 (18)
C4—C3—C2	111.61 (18)	C8—C9—H9	121.1
C4—C3—H3A	109.3	C10—C9—H9	121.1
C2—C3—H3A	109.3	C11—C10—C9	121.85 (18)
C4—C3—H3B	109.3	C11—C10—S1	119.82 (15)
C2—C3—H3B	109.3	C9—C10—S1	118.23 (15)
H3A—C3—H3B	108.0	C12—C11—C10	119.89 (18)
C5—C4—C3	111.52 (17)	C12—C11—H11	120.1
C5—C4—H4A	109.3	C10—C11—H11	120.1
C3—C4—H4A	109.3	C13—C12—C11	118.07 (19)
C5—C4—H4B	109.3	C13—C12—H12	121.0
C3—C4—H4B	109.3	C11—C12—H12	121.0
H4A—C4—H4B	108.0	C12—C13—C8	121.94 (18)
C4—C5—C6	111.71 (17)	C12—C13—N1	126.75 (18)
C4—C5—H5A	109.3	C8—C13—N1	111.29 (17)
C6—C5—H5A	109.3

C13—N1—C1—C2	172.04 (19)	C13—C8—C9—C10	−0.6 (3)
C13—N1—C1—C6	0.1 (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—C3	54.2 (2)	C8—C9—C10—S1	174.85 (15)
C1—C2—C3—C4	−54.0 (2)	O2—S1—C10—C11	−139.60 (16)
C2—C3—C4—C5	58.2 (2)	O1—S1—C10—C11	−10.09 (19)
C3—C4—C5—C6	−56.1 (2)	N2—S1—C10—C11	104.33 (17)
N1—C1—C6—C8	1.3 (2)	O2—S1—C10—C9	44.03 (18)
C2—C1—C6—C8	−171.03 (18)	O1—S1—C10—C9	173.54 (15)
N1—C1—C6—C7	−117.0 (2)	N2—S1—C10—C9	−72.03 (17)
C2—C1—C6—C7	70.6 (2)	C9—C10—C11—C12	1.8 (3)
N1—C1—C6—C5	119.95 (19)	S1—C10—C11—C12	−174.46 (15)
C2—C1—C6—C5	−52.4 (2)	C10—C11—C12—C13	0.0 (3)
C4—C5—C6—C8	159.10 (17)	C11—C12—C13—C8	−2.0 (3)
C4—C5—C6—C1	50.0 (2)	C11—C12—C13—N1	176.45 (19)
C4—C5—C6—C7	−73.1 (2)	C9—C8—C13—C12	2.3 (3)
C1—C6—C8—C9	176.5 (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—C9	62.1 (3)	C6—C8—C13—N1	2.6 (2)
C1—C6—C8—C13	−2.2 (2)	C1—N1—C13—C12	179.7 (2)
C7—C6—C8—C13	115.73 (19)	C1—N1—C13—C8	−1.7 (2)
C5—C6—C8—C13	−116.70 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···N1ⁱ	0.86 (3)	2.13 (3)	2.986 (3)	170 (2)
N2—H2···O1ⁱⁱ	0.86 (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.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₆N₂O₂S
M_r	264.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.3694 (5), 10.4051 (5), 13.5937 (8)
β (°)	103.516 (6)
V (Å³)	1288.54 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.25 × 0.20 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.941, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	5426, 2959, 2364
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.121, 1.05
No. of reflections	2959
No. of parameters	171
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.48

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···N1ⁱ	0.86 (3)	2.13 (3)	2.986 (3)	170 (2)
N2—H2···O1ⁱⁱ	0.86 (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.

Footnotes

‡Additional correspondence author, e-mail: aasiri2@kau.edu.sa.

Acknowledgements

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).

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