4a-Methyl-2,3,4,4a-tetra-hydro-1H-carbazole-6-sulfonamide.

In the title mol-ecule, C(13)H(16)N(2)O(2)S, 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 inter-molecular 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 mol-ecule 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 = 264.34

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.121

S = 1.05

2959 reflections

171 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.79 e Å−3

Δρmin = −0.48 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010239/xu5479sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812010239/xu5479Isup3.cml

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

C13H16N2O2S	F(000) = 560
Mr = 264.34	Dx = 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

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	Rint = 0.030
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.4°
ω scan	h = −8→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→13
Tmin = 0.941, Tmax = 0.976	l = −17→17
5426 measured reflections

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(Fo2) + (0.0503P)2 + 0.7098P] where P = (Fo2 + 2Fc2)/3
2959 reflections	(Δ/σ)max = 0.001
171 parameters	Δρmax = 0.79 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) ; (ii) .