2-{N-[(2,3,4,9-Tetra-hydro-1H-carbazol-3-yl)meth-yl]methyl-sulfonamido}-ethyl methane-sulfonate.

In the title compound, C17H24N2O5S2, the indole ring system is nearly planar [maximum deviation = 0.032 (1) Å] and the cyclo-hexene ring has a half-chair conformation. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into a chain running along the b-axis direction. Weak C-H⋯O hydrogen bonds and weak C-H⋯π inter-actions are observed between the chains.

Related literature

For tetra­hydro­n class="Chemical">carbazole systems present in the framework of a number of indole-type alkaloids of biological inter­est, see: Saxton (1983 ▶). For the anti­tumor activity of tetra­hydro­carbazoles containing an amine unit, see: Chen et al. (2009 ▶). For the most potent drugs, such as ellipcitine and olivacine, for the treatment of a variety of cancers, see: Pelletier (1970 ▶). For the use of tetra­hydro­carbazoles in the synthesis of pyridocarbazoles, see: Knölker & Reddy (2002 ▶). For related structures, see: Patır et al. (1997 ▶); Gündoğdu et al. (2011 ▶); Göçmen­türk et al. (2013 ▶).

Experimental

Crystal data

C17H24N2O5S2

M = 400.50

Monoclinic,

a = 5.4399 (2) Å

b = 18.0322 (6) Å

c = 19.0103 (6) Å

β = 98.973 (2)°

V = 1841.96 (11) Å3

Z = 4

Cu Kα radiation

μ = 2.90 mm−1

T = 150 K

0.18 × 0.16 × 0.13 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.623, T max = 0.686

47392 measured reflections

3472 independent reflections

3357 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.090

S = 1.05

3472 reflections

241 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAIn class="Chemical">NT (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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813034016/xu5758sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034016/xu5758Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813034016/xu5758Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H24N2O5S2	F(000) = 848
Mr = 400.50	Dx = 1.444 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 9016 reflections
a = 5.4399 (2) Å	θ = 3.4–69.5°
b = 18.0322 (6) Å	µ = 2.90 mm−1
c = 19.0103 (6) Å	T = 150 K
β = 98.973 (2)°	Plate, colourless
V = 1841.96 (11) Å3	0.18 × 0.16 × 0.13 mm
Z = 4

Bruker Kappa APEXII CCD area-detector diffractometer	3472 independent reflections
Radiation source: fine-focus sealed tube	3357 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
φ and ω scans	θmax = 69.8°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→6
Tmin = 0.623, Tmax = 0.686	k = −20→21
47392 measured reflections	l = −23→23

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0569P)2 + 0.6777P] where P = (Fo2 + 2Fc2)/3
3472 reflections	(Δ/σ)max < 0.001
241 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.19263 (6)	−0.204476 (18)	0.209478 (18)	0.02367 (12)
S2	0.21420 (6)	0.077279 (19)	0.091542 (18)	0.02505 (12)
O1	0.0230 (2)	−0.20118 (6)	0.25961 (6)	0.0344 (3)
O2	0.0933 (2)	−0.21216 (6)	0.13524 (6)	0.0339 (3)
O3	0.34759 (19)	0.01082 (6)	0.13520 (5)	0.0276 (2)
O4	0.3080 (2)	0.14168 (6)	0.12962 (6)	0.0368 (3)
O5	0.2426 (2)	0.06975 (6)	0.01834 (6)	0.0328 (3)
N1	0.3567 (2)	−0.12840 (6)	0.21645 (6)	0.0218 (2)
N9	0.2800 (2)	0.16928 (7)	0.40969 (7)	0.0264 (3)
H9	0.161 (4)	0.1983 (11)	0.4018 (10)	0.035 (5)*
C1	0.1172 (3)	0.07536 (8)	0.31395 (8)	0.0252 (3)
H1A	0.1370	0.1042	0.2709	0.030*
H1B	−0.0549	0.0824	0.3236	0.030*
C2	0.1640 (2)	−0.00717 (8)	0.30133 (8)	0.0243 (3)
H2A	0.0927	−0.0369	0.3370	0.029*
H2B	0.0768	−0.0213	0.2536	0.029*
C3	0.4407 (2)	−0.02574 (7)	0.30626 (7)	0.0210 (3)
H3	0.5135	0.0055	0.2713	0.025*
C4	0.5787 (2)	−0.00923 (7)	0.38158 (7)	0.0215 (3)
H4A	0.5346	−0.0471	0.4152	0.026*
H4B	0.7606	−0.0117	0.3817	0.026*
C4A	0.5100 (3)	0.06626 (7)	0.40525 (7)	0.0217 (3)
C5	0.8579 (3)	0.10872 (8)	0.50849 (8)	0.0265 (3)
H5	0.9663	0.0676	0.5071	0.032*
C5A	0.6340 (3)	0.11314 (7)	0.46082 (7)	0.0229 (3)
C6	0.9185 (3)	0.16495 (9)	0.55752 (8)	0.0315 (3)
H6	1.0704	0.1624	0.5898	0.038*
C7	0.7590 (3)	0.22570 (9)	0.56039 (8)	0.0338 (4)
H7	0.8029	0.2628	0.5956	0.041*
C8	0.5396 (3)	0.23279 (8)	0.51321 (8)	0.0318 (3)
H8	0.4330	0.2743	0.5149	0.038*
C8A	0.4810 (3)	0.17645 (8)	0.46293 (7)	0.0253 (3)
C9A	0.2978 (3)	0.10205 (8)	0.37574 (7)	0.0233 (3)
C10	0.4772 (3)	−0.10741 (7)	0.28916 (7)	0.0228 (3)
H10A	0.6576	−0.1180	0.2940	0.027*
H10B	0.4078	−0.1384	0.3243	0.027*
C11	0.4043 (3)	−0.27709 (9)	0.23392 (10)	0.0360 (4)
H11A	0.5265	−0.2786	0.2011	0.054*
H11B	0.3142	−0.3243	0.2317	0.054*
H11C	0.4902	−0.2689	0.2826	0.054*
C12	0.4941 (3)	−0.11271 (8)	0.15714 (8)	0.0251 (3)
H12A	0.5300	−0.1600	0.1344	0.030*
H12B	0.6551	−0.0892	0.1762	0.030*
C13	0.3519 (3)	−0.06250 (8)	0.10170 (8)	0.0264 (3)
H13A	0.4356	−0.0598	0.0591	0.032*
H13B	0.1804	−0.0812	0.0871	0.032*
C14	−0.0999 (3)	0.06534 (9)	0.09937 (9)	0.0344 (4)
H14B	−0.1577	0.0172	0.0792	0.052*
H14A	−0.1987	0.1050	0.0735	0.052*
H14C	−0.1191	0.0670	0.1498	0.052*

	U11	U22	U33	U12	U13	U23
S1	0.02243 (19)	0.02128 (19)	0.0264 (2)	−0.00275 (12)	0.00095 (14)	−0.00032 (12)
S2	0.0270 (2)	0.0233 (2)	0.0241 (2)	−0.00371 (12)	0.00149 (14)	0.00101 (12)
O1	0.0284 (5)	0.0383 (6)	0.0378 (6)	−0.0057 (4)	0.0092 (5)	0.0024 (5)
O2	0.0369 (6)	0.0322 (6)	0.0296 (6)	−0.0095 (5)	−0.0040 (5)	−0.0024 (4)
O3	0.0334 (6)	0.0244 (5)	0.0238 (5)	−0.0008 (4)	0.0004 (4)	0.0004 (4)
O4	0.0429 (6)	0.0259 (6)	0.0385 (6)	−0.0081 (5)	−0.0030 (5)	−0.0022 (5)
O5	0.0395 (6)	0.0337 (6)	0.0256 (6)	−0.0008 (5)	0.0062 (5)	0.0050 (4)
N1	0.0236 (6)	0.0200 (6)	0.0217 (6)	−0.0010 (4)	0.0029 (4)	−0.0018 (4)
N9	0.0280 (6)	0.0215 (6)	0.0297 (7)	0.0076 (5)	0.0042 (5)	−0.0005 (5)
C1	0.0230 (7)	0.0234 (7)	0.0287 (7)	0.0035 (5)	0.0021 (6)	0.0012 (5)
C2	0.0210 (6)	0.0231 (7)	0.0283 (7)	0.0006 (5)	0.0020 (5)	−0.0005 (5)
C3	0.0216 (6)	0.0190 (6)	0.0227 (7)	0.0001 (5)	0.0039 (5)	−0.0003 (5)
C4	0.0212 (6)	0.0207 (6)	0.0226 (7)	0.0024 (5)	0.0032 (5)	−0.0003 (5)
C4A	0.0237 (6)	0.0202 (6)	0.0218 (7)	0.0015 (5)	0.0059 (5)	0.0002 (5)
C5	0.0295 (7)	0.0254 (7)	0.0241 (7)	0.0012 (6)	0.0026 (6)	0.0006 (5)
C5A	0.0276 (7)	0.0212 (7)	0.0207 (6)	0.0000 (5)	0.0065 (5)	0.0010 (5)
C6	0.0363 (8)	0.0309 (8)	0.0255 (7)	−0.0042 (6)	−0.0008 (6)	−0.0002 (6)
C7	0.0492 (9)	0.0253 (7)	0.0262 (7)	−0.0048 (7)	0.0045 (7)	−0.0061 (6)
C8	0.0442 (9)	0.0218 (7)	0.0304 (8)	0.0029 (6)	0.0090 (7)	−0.0024 (6)
C8A	0.0317 (7)	0.0218 (7)	0.0235 (7)	0.0018 (6)	0.0073 (6)	0.0013 (5)
C9A	0.0246 (7)	0.0210 (7)	0.0251 (7)	0.0019 (5)	0.0062 (5)	0.0009 (5)
C10	0.0241 (7)	0.0209 (7)	0.0224 (7)	0.0014 (5)	0.0004 (5)	−0.0013 (5)
C11	0.0378 (9)	0.0207 (7)	0.0474 (10)	0.0012 (6)	0.0001 (7)	0.0010 (7)
C12	0.0243 (7)	0.0255 (7)	0.0262 (7)	0.0000 (5)	0.0062 (6)	−0.0001 (5)
C13	0.0310 (7)	0.0244 (7)	0.0239 (7)	−0.0016 (6)	0.0047 (6)	−0.0016 (5)
C14	0.0279 (8)	0.0381 (8)	0.0371 (9)	−0.0018 (6)	0.0049 (6)	−0.0067 (7)

S1—O1	1.4273 (12)	C4A—C9A	1.365 (2)
S1—O2	1.4370 (11)	C5—C6	1.382 (2)
S1—N1	1.6306 (12)	C5—H5	0.9500
S1—C11	1.7576 (16)	C5A—C4A	1.4363 (19)
S2—O3	1.5697 (10)	C5A—C5	1.402 (2)
S2—O4	1.4205 (11)	C5A—C8A	1.4169 (19)
S2—O5	1.4303 (11)	C6—C7	1.404 (2)
S2—C14	1.7516 (16)	C6—H6	0.9500
O3—C13	1.4693 (17)	C7—C8	1.383 (2)
N1—C10	1.4836 (17)	C7—H7	0.9500
N1—C12	1.4742 (18)	C8—C8A	1.397 (2)
N9—C8A	1.3753 (19)	C8—H8	0.9500
N9—C9A	1.3837 (18)	C9A—C1	1.489 (2)
N9—H9	0.83 (2)	C10—H10A	0.9900
C1—C2	1.5350 (19)	C10—H10B	0.9900
C1—H1A	0.9900	C11—H11A	0.9800
C1—H1B	0.9900	C11—H11B	0.9800
C2—C3	1.5304 (18)	C11—H11C	0.9800
C2—H2A	0.9900	C12—C13	1.508 (2)
C2—H2B	0.9900	C12—H12A	0.9900
C3—C4	1.5386 (18)	C12—H12B	0.9900
C3—C10	1.5278 (18)	C13—H13A	0.9900
C3—H3	1.0000	C13—H13B	0.9900
C4—H4A	0.9900	C14—H14B	0.9800
C4—H4B	0.9900	C14—H14A	0.9800
C4A—C4	1.4992 (18)	C14—H14C	0.9800
O1—S1—O2	118.47 (7)	C5—C5A—C4A	134.64 (13)
O1—S1—N1	108.26 (6)	C5—C5A—C8A	118.82 (13)
O1—S1—C11	108.63 (8)	C8A—C5A—C4A	106.54 (12)
O2—S1—N1	106.15 (6)	C5—C6—C7	120.98 (14)
O2—S1—C11	108.56 (8)	C5—C6—H6	119.5
N1—S1—C11	106.12 (7)	C7—C6—H6	119.5
O3—S2—C14	103.76 (7)	C6—C7—H7	119.2
O4—S2—O3	104.78 (6)	C8—C7—C6	121.55 (14)
O4—S2—O5	119.25 (7)	C8—C7—H7	119.2
O4—S2—C14	109.56 (8)	C7—C8—C8A	117.27 (14)
O5—S2—O3	109.32 (6)	C7—C8—H8	121.4
O5—S2—C14	109.02 (8)	C8A—C8—H8	121.4
C13—O3—S2	119.68 (9)	N9—C8A—C5A	107.83 (12)
C10—N1—S1	116.55 (9)	N9—C8A—C8	129.95 (14)
C12—N1—S1	115.83 (9)	C8—C8A—C5A	122.21 (14)
C12—N1—C10	117.43 (11)	N9—C9A—C1	124.46 (12)
C8A—N9—C9A	108.69 (12)	C4A—C9A—N9	109.80 (13)
C8A—N9—H9	125.7 (13)	C4A—C9A—C1	125.68 (13)
C9A—N9—H9	125.3 (13)	N1—C10—C3	113.02 (11)
C2—C1—H1A	109.8	N1—C10—H10A	109.0
C2—C1—H1B	109.8	N1—C10—H10B	109.0
C9A—C1—C2	109.37 (11)	C3—C10—H10A	109.0
C9A—C1—H1A	109.8	C3—C10—H10B	109.0
C9A—C1—H1B	109.8	H10A—C10—H10B	107.8
H1A—C1—H1B	108.2	S1—C11—H11A	109.5
C1—C2—H2A	109.0	S1—C11—H11B	109.5
C1—C2—H2B	109.0	S1—C11—H11C	109.5
C3—C2—C1	112.84 (11)	H11A—C11—H11B	109.5
C3—C2—H2A	109.0	H11A—C11—H11C	109.5
C3—C2—H2B	109.0	H11B—C11—H11C	109.5
H2A—C2—H2B	107.8	N1—C12—C13	112.57 (11)
C2—C3—C4	110.32 (11)	N1—C12—H12A	109.1
C2—C3—H3	108.9	N1—C12—H12B	109.1
C4—C3—H3	108.9	C13—C12—H12A	109.1
C10—C3—C2	110.92 (11)	C13—C12—H12B	109.1
C10—C3—C4	108.89 (11)	H12A—C12—H12B	107.8
C10—C3—H3	108.9	O3—C13—C12	106.16 (11)
C3—C4—H4A	109.6	O3—C13—H13A	110.5
C3—C4—H4B	109.6	O3—C13—H13B	110.5
C4A—C4—C3	110.28 (11)	C12—C13—H13A	110.5
C4A—C4—H4A	109.6	C12—C13—H13B	110.5
C4A—C4—H4B	109.6	H13A—C13—H13B	108.7
H4A—C4—H4B	108.1	S2—C14—H14B	109.5
C5A—C4A—C4	130.15 (13)	S2—C14—H14A	109.5
C9A—C4A—C5A	107.10 (12)	S2—C14—H14C	109.5
C9A—C4A—C4	122.73 (13)	H14B—C14—H14A	109.5
C5A—C5—H5	120.5	H14B—C14—H14C	109.5
C6—C5—C5A	119.09 (14)	H14A—C14—H14C	109.5
C6—C5—H5	120.5
O1—S1—N1—C10	50.95 (11)	C5A—C4A—C4—C3	−161.46 (13)
O1—S1—N1—C12	−164.56 (10)	C9A—C4A—C4—C3	20.88 (18)
O2—S1—N1—C10	179.12 (10)	C4—C4A—C9A—N9	178.07 (12)
O2—S1—N1—C12	−36.39 (11)	C4—C4A—C9A—C1	−4.8 (2)
C11—S1—N1—C10	−65.50 (12)	C5A—C4A—C9A—N9	−0.06 (16)
C11—S1—N1—C12	78.99 (12)	C5A—C4A—C9A—C1	177.07 (13)
O4—S2—O3—C13	−162.57 (10)	C5A—C5—C6—C7	0.4 (2)
O5—S2—O3—C13	−33.66 (12)	C5—C5A—C4A—C4	3.9 (3)
C14—S2—O3—C13	82.53 (11)	C5—C5A—C4A—C9A	−178.12 (16)
S2—O3—C13—C12	179.57 (9)	C8A—C5A—C4A—C4	−176.65 (13)
S1—N1—C10—C3	−133.41 (10)	C8A—C5A—C4A—C9A	1.29 (15)
C12—N1—C10—C3	82.67 (14)	C4A—C5A—C5—C6	−178.55 (15)
S1—N1—C12—C13	94.59 (12)	C8A—C5A—C5—C6	2.1 (2)
C10—N1—C12—C13	−121.24 (13)	C4A—C5A—C8A—N9	−2.05 (15)
C9A—N9—C8A—C5A	2.05 (16)	C4A—C5A—C8A—C8	177.19 (13)
C9A—N9—C8A—C8	−177.12 (15)	C5—C5A—C8A—N9	177.48 (13)
C8A—N9—C9A—C1	−178.42 (13)	C5—C5A—C8A—C8	−3.3 (2)
C8A—N9—C9A—C4A	−1.25 (16)	C5—C6—C7—C8	−1.9 (2)
C9A—C1—C2—C3	−43.77 (16)	C6—C7—C8—C8A	0.8 (2)
C1—C2—C3—C4	62.50 (15)	C7—C8—C8A—N9	−179.12 (15)
C1—C2—C3—C10	−176.76 (11)	C7—C8—C8A—C5A	1.8 (2)
C2—C3—C4—C4A	−47.92 (15)	N9—C9A—C1—C2	−167.67 (13)
C10—C3—C4—C4A	−169.87 (11)	C4A—C9A—C1—C2	15.6 (2)
C2—C3—C10—N1	60.12 (15)	N1—C12—C13—O3	69.55 (14)
C4—C3—C10—N1	−178.29 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O2i	0.83 (2)	2.17 (2)	2.9804 (16)	166 (2)
C11—H11C···O4ii	0.98	2.45	3.171 (2)	130
C13—H13A···O5iii	0.99	2.46	3.4148 (19)	161
C14—H14B···O5iv	0.98	2.42	3.317 (2)	152
C11—H11A···Cg2ii	0.98	2.95	3.6705 (19)	131

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C4a/C5a/C8a/N9/C9a ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9⋯O2i	0.83 (2)	2.17 (2)	2.9804 (16)	166 (2)
C11—H11C⋯O4ii	0.98	2.45	3.171 (2)	130
C13—H13A⋯O5iii	0.99	2.46	3.4148 (19)	161
C14—H14B⋯O5iv	0.98	2.42	3.317 (2)	152
C11—H11A⋯Cg2ii	0.98	2.95	3.6705 (19)	131

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .