3,3-Ethyl-enedithio-3,3a,4,5,10,10b-hexa-hydro-2H-furo[2,3-a]carbazole.

The title compound, C(16)H(17)NOS(2), consists of a carbazole skeleton with tetra-hydro-furan and dithiol-ane rings. In the indole ring system, the benzene and pyrrole rings are nearly coplanar, forming a dihedral angle of 1.57 (15)°. The cyclo-hexenone and tetra-hydro-furan rings have envelope conformations, while the dithiol-ane ring adopts a twist conformation. In the crystal structure, pairs of weak inter-molecular N-H⋯S hydrogen bonds link the mol-ecules into centrosymmetric dimers with R(2) (2)(16) ring motifs. Weak C-H⋯π inter-actions may further stabilize the structure.

Related literature

For general background, see: Phillipson & Zenk (1980 ▶); Saxton (1983 ▶); Abraham (1975 ▶). For related structures, see: Hökelek et al. (1994 ▶, 1998 ▶, 1999 ▶, 2004 ▶, 2006 ▶); Patır et al. (1997 ▶); Hökelek & Patır (1999 ▶,2002 ▶); Çaylak et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶)

Experimental

Crystal data

C16H17NOS2

M = 303.43

Orthorhombic,

a = 21.7617 (5) Å

b = 8.4992 (2) Å

c = 15.2115 (3) Å

V = 2813.47 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.37 mm−1

T = 294 K

0.35 × 0.20 × 0.15 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.913, T max = 0.944

8196 measured reflections

2289 independent reflections

1105 reflections with I > 2σ(I)

R int = 0.149

3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.108

S = 0.98

2289 reflections

185 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006035/xu2478sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006035/xu2478Isup2.hkl

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

C16H17NOS2	F(000) = 1280
Mr = 303.43	Dx = 1.433 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 25 reflections
a = 21.7617 (5) Å	θ = 9.3–16.7°
b = 8.4992 (2) Å	µ = 0.37 mm−1
c = 15.2115 (3) Å	T = 294 K
V = 2813.47 (11) Å3	Prism, colorless
Z = 8	0.35 × 0.20 × 0.15 mm

Enraf–Nonius TurboCAD-4 diffractometer	1105 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.149
graphite	θmax = 24.3°, θmin = 2.6°
Non–profiled ω scans	h = −25→25
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
Tmin = 0.913, Tmax = 0.944	l = −17→0
8196 measured reflections	3 standard reflections every 120 min
2289 independent reflections	intensity decay: 1%

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.0328P)2 + 1.8766P] where P = (Fo2 + 2Fc2)/3
2289 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	0.32178 (5)	0.10773 (14)	0.23756 (8)	0.0538 (4)
S2	0.33505 (5)	−0.00621 (14)	0.05706 (9)	0.0538 (3)
O1	0.48005 (12)	0.0372 (3)	0.1141 (2)	0.0597 (9)
C2	0.43301 (17)	−0.0004 (5)	0.1754 (3)	0.0499 (12)
H2A	0.4450	0.0310	0.2343	0.060*
H2B	0.4250	−0.1126	0.1753	0.060*
C3	0.37602 (18)	0.0902 (5)	0.1461 (3)	0.0394 (11)
C3A	0.40456 (17)	0.2447 (4)	0.1109 (3)	0.0391 (11)
H3A	0.3786	0.2865	0.0637	0.047*
C4	0.41256 (17)	0.3698 (4)	0.1817 (3)	0.0402 (11)
H4A	0.3724	0.4058	0.2008	0.048*
H4B	0.4332	0.3238	0.2320	0.048*
C5	0.44962 (17)	0.5095 (5)	0.1485 (3)	0.0423 (11)
H5A	0.4272	0.5632	0.1023	0.051*
H5B	0.4566	0.5834	0.1961	0.051*
C5A	0.50957 (18)	0.4512 (4)	0.1140 (3)	0.0375 (10)
C5B	0.56863 (19)	0.5223 (5)	0.1102 (3)	0.0402 (11)
C6	0.5923 (2)	0.6705 (5)	0.1333 (3)	0.0487 (12)
H6	0.5664	0.7483	0.1552	0.058*
C7	0.6542 (2)	0.6994 (6)	0.1233 (3)	0.0582 (14)
H7	0.6700	0.7973	0.1384	0.070*
C8	0.6930 (2)	0.5844 (7)	0.0909 (3)	0.0608 (14)
H8	0.7347	0.6070	0.0850	0.073*
C9	0.6721 (2)	0.4373 (5)	0.0671 (3)	0.0562 (13)
H9	0.6985	0.3607	0.0454	0.067*
C9A	0.60977 (19)	0.4090 (5)	0.0771 (3)	0.0426 (11)
C10A	0.51613 (17)	0.3010 (5)	0.0837 (3)	0.0365 (11)
C10B	0.46569 (17)	0.1854 (4)	0.0715 (3)	0.0401 (11)
H10B	0.4600	0.1667	0.0085	0.048*
N10	0.57621 (16)	0.2746 (5)	0.0610 (3)	0.0469 (10)
H10	0.5901 (17)	0.196 (4)	0.038 (3)	0.043 (15)*
C11	0.2649 (2)	−0.0299 (5)	0.1985 (3)	0.0658 (14)
H11A	0.2507	−0.0947	0.2469	0.079*
H11B	0.2299	0.0269	0.1750	0.079*
C12	0.2921 (2)	−0.1318 (5)	0.1286 (3)	0.0646 (14)
H12A	0.2599	−0.1851	0.0961	0.078*
H12B	0.3188	−0.2106	0.1545	0.078*

	U11	U22	U33	U12	U13	U23
S1	0.0516 (7)	0.0527 (7)	0.0570 (8)	−0.0052 (6)	0.0097 (7)	−0.0042 (7)
S2	0.0541 (7)	0.0516 (7)	0.0558 (7)	−0.0125 (7)	−0.0012 (6)	−0.0103 (7)
O1	0.0462 (19)	0.040 (2)	0.093 (3)	0.0094 (14)	0.0183 (18)	0.0122 (18)
C2	0.042 (2)	0.042 (2)	0.065 (3)	0.001 (2)	0.001 (2)	0.008 (3)
C3	0.039 (3)	0.036 (2)	0.042 (3)	−0.003 (2)	−0.001 (2)	−0.001 (2)
C3A	0.038 (2)	0.035 (2)	0.045 (3)	0.0018 (19)	−0.002 (2)	0.000 (2)
C4	0.034 (2)	0.041 (3)	0.047 (3)	0.000 (2)	0.004 (2)	−0.007 (2)
C5	0.048 (3)	0.036 (2)	0.043 (3)	0.001 (2)	−0.001 (2)	−0.004 (2)
C5A	0.040 (3)	0.040 (3)	0.033 (3)	0.000 (2)	0.002 (2)	−0.001 (2)
C5B	0.050 (3)	0.042 (3)	0.029 (2)	−0.003 (2)	−0.001 (2)	0.001 (2)
C6	0.059 (3)	0.049 (3)	0.038 (3)	−0.005 (2)	0.002 (2)	0.002 (2)
C7	0.067 (3)	0.061 (3)	0.046 (3)	−0.025 (3)	−0.002 (3)	0.006 (3)
C8	0.047 (3)	0.082 (4)	0.054 (3)	−0.017 (3)	0.000 (2)	0.009 (3)
C9	0.049 (3)	0.059 (3)	0.061 (3)	−0.003 (3)	0.007 (3)	0.005 (3)
C9A	0.044 (3)	0.046 (3)	0.038 (3)	−0.007 (2)	−0.001 (2)	0.003 (2)
C10A	0.034 (3)	0.040 (3)	0.036 (3)	0.002 (2)	−0.002 (2)	0.002 (2)
C10B	0.042 (3)	0.034 (2)	0.045 (3)	−0.004 (2)	0.004 (2)	0.000 (2)
N10	0.042 (2)	0.040 (2)	0.059 (3)	0.004 (2)	0.011 (2)	−0.006 (2)
C11	0.051 (3)	0.066 (4)	0.080 (4)	−0.017 (3)	0.005 (3)	0.002 (3)
C12	0.070 (3)	0.048 (3)	0.076 (4)	−0.020 (3)	0.004 (3)	−0.007 (3)

S1—C3	1.830 (4)	C5B—C6	1.405 (5)
S1—C11	1.803 (4)	C6—H6	0.9300
S2—C3	1.817 (4)	C7—C6	1.377 (5)
S2—C12	1.788 (4)	C7—C8	1.383 (6)
O1—C2	1.421 (5)	C7—H7	0.9300
O1—C10B	1.450 (4)	C8—H8	0.9300
C2—H2A	0.9700	C9—C8	1.379 (6)
C2—H2B	0.9700	C9—H9	0.9300
C3—C2	1.526 (5)	C9A—C9	1.385 (5)
C3A—C3	1.548 (5)	C9A—C5B	1.408 (5)
C3A—C4	1.523 (5)	C10A—C10B	1.485 (5)
C3A—C10B	1.544 (5)	C10B—H10B	0.9800
C3A—H3A	0.9800	N10—C10A	1.371 (5)
C4—C5	1.522 (5)	N10—C9A	1.378 (5)
C4—H4A	0.9700	N10—H10	0.81 (3)
C4—H4B	0.9700	C11—H11A	0.9700
C5—H5A	0.9700	C11—H11B	0.9700
C5—H5B	0.9700	C12—C11	1.495 (6)
C5A—C5	1.491 (5)	C12—H12A	0.9700
C5A—C10A	1.365 (5)	C12—H12B	0.9700
C5B—C5A	1.421 (5)
C11—S1—C3	98.0 (2)	C5B—C6—H6	120.3
C12—S2—C3	94.1 (2)	C7—C6—C5B	119.3 (4)
C2—O1—C10B	109.5 (3)	C7—C6—H6	120.3
O1—C2—C3	106.3 (3)	C6—C7—C8	120.8 (4)
O1—C2—H2A	110.5	C6—C7—H7	119.6
O1—C2—H2B	110.5	C8—C7—H7	119.6
C3—C2—H2A	110.5	C9—C8—C7	122.1 (4)
C3—C2—H2B	110.5	C9—C8—H8	119.0
H2A—C2—H2B	108.7	C7—C8—H8	119.0
S2—C3—S1	106.7 (2)	C8—C9—C9A	116.9 (4)
C2—C3—S1	110.1 (3)	C8—C9—H9	121.5
C2—C3—S2	112.9 (3)	C9A—C9—H9	121.5
C2—C3—C3A	101.7 (3)	C9—C9A—C5B	122.9 (4)
C3A—C3—S1	116.9 (3)	N10—C9A—C9	130.1 (4)
C3A—C3—S2	108.7 (3)	N10—C9A—C5B	107.1 (4)
C3—C3A—H3A	109.3	O1—C10B—C3A	107.2 (3)
C4—C3A—C3	113.2 (3)	O1—C10B—C10A	111.1 (3)
C4—C3A—H3A	109.3	O1—C10B—H10B	108.9
C4—C3A—C10B	113.8 (3)	N10—C10A—C10B	124.4 (4)
C10B—C3A—C3	101.7 (3)	C3A—C10B—H10B	108.9
C10B—C3A—H3A	109.3	C5A—C10A—N10	109.8 (4)
C3A—C4—H4A	109.3	C5A—C10A—C10B	125.7 (4)
C3A—C4—H4B	109.3	C10A—C10B—C3A	111.9 (3)
C5—C4—C3A	111.8 (3)	C10A—C10B—H10B	108.9
C5—C4—H4A	109.3	C9A—N10—H10	124 (3)
C5—C4—H4B	109.3	C10A—N10—C9A	109.0 (4)
H4A—C4—H4B	107.9	C10A—N10—H10	127 (3)
C4—C5—H5A	109.9	S1—C11—H11A	109.7
C4—C5—H5B	109.9	S1—C11—H11B	109.7
C5A—C5—C4	108.7 (3)	C12—C11—S1	109.8 (3)
C5A—C5—H5A	109.9	C12—C11—H11A	109.7
C5A—C5—H5B	109.9	C12—C11—H11B	109.7
H5A—C5—H5B	108.3	H11A—C11—H11B	108.2
C5B—C5A—C5	131.6 (4)	S2—C12—H12A	110.3
C10A—C5A—C5	121.4 (4)	S2—C12—H12B	110.3
C10A—C5A—C5B	106.8 (4)	C11—C12—S2	107.1 (3)
C6—C5B—C5A	134.6 (4)	C11—C12—H12A	110.3
C6—C5B—C9A	118.0 (4)	C11—C12—H12B	110.3
C9A—C5B—C5A	107.4 (4)	H12A—C12—H12B	108.6
C11—S1—C3—S2	15.4 (3)	C5A—C5B—C6—C7	177.8 (4)
C11—S1—C3—C2	−107.4 (3)	C9A—C5B—C6—C7	−0.2 (6)
C11—S1—C3—C3A	137.2 (3)	C5—C5A—C10A—N10	−176.3 (4)
C3—S1—C11—C12	17.0 (4)	C5—C5A—C10A—C10B	7.2 (6)
C12—S2—C3—S1	−36.2 (2)	C5B—C5A—C10A—N10	−0.1 (5)
C12—S2—C3—C2	84.9 (3)	C5B—C5A—C10A—C10B	−176.6 (4)
C12—S2—C3—C3A	−163.1 (3)	C6—C5B—C5A—C5	−2.7 (8)
C3—S2—C12—C11	49.5 (4)	C6—C5B—C5A—C10A	−178.4 (5)
C10B—O1—C2—C3	22.4 (4)	C9A—C5B—C5A—C5	175.4 (4)
C2—O1—C10B—C3A	0.5 (4)	C9A—C5B—C5A—C10A	−0.2 (4)
C2—O1—C10B—C10A	123.0 (4)	C8—C7—C6—C5B	−0.1 (7)
C4—C3A—C3—S1	31.6 (4)	C6—C7—C8—C9	0.2 (7)
C4—C3A—C3—S2	152.4 (3)	C9A—C9—C8—C7	0.0 (7)
C4—C3A—C3—C2	−88.3 (4)	N10—C9A—C5B—C5A	0.5 (4)
C10B—C3A—C3—S1	154.1 (3)	N10—C9A—C5B—C6	179.0 (4)
C10B—C3A—C3—S2	−85.1 (3)	C9—C9A—C5B—C5A	−178.1 (4)
C10B—C3A—C3—C2	34.2 (4)	C9—C9A—C5B—C6	0.4 (6)
C3—C3A—C4—C5	171.0 (3)	N10—C9A—C9—C8	−178.5 (4)
C10B—C3A—C4—C5	55.6 (4)	C5B—C9A—C9—C8	−0.3 (6)
C4—C3A—C10B—O1	99.6 (4)	N10—C10A—C10B—O1	55.3 (5)
C3—C3A—C10B—O1	−22.4 (4)	N10—C10A—C10B—C3A	175.1 (4)
C4—C3A—C10B—C10A	−22.4 (5)	C5A—C10A—C10B—O1	−128.7 (4)
C3—C3A—C10B—C10A	−144.4 (3)	C5A—C10A—C10B—C3A	−9.0 (6)
S1—C3—C2—O1	−160.3 (3)	C9A—N10—C10A—C5A	0.4 (5)
S2—C3—C2—O1	80.6 (4)	C9A—N10—C10A—C10B	176.9 (4)
C3A—C3—C2—O1	−35.7 (4)	C10A—N10—C9A—C5B	−0.5 (5)
C3A—C4—C5—C5A	−55.3 (4)	C10A—N10—C9A—C9	177.8 (4)
C5B—C5A—C5—C4	−149.7 (4)	S2—C12—C11—S1	−44.2 (4)
C10A—C5A—C5—C4	25.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···S2i	0.81 (4)	2.71 (4)	3.487 (4)	161 (4)
C3A—H3A···Cg2ii	0.98	2.85	3.725 (4)	149
C4—H4B···Cg1iii	0.97	2.79	3.556 (5)	136
C5—H5A···Cg1ii	0.97	2.96	3.714 (5)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10⋯S2i	0.81 (4)	2.71 (4)	3.487 (4)	161 (4)
C3A—H3A⋯Cg2ii	0.98	2.85	3.725 (4)	149
C4—H4B⋯Cg1iii	0.97	2.79	3.556 (5)	136
C5—H5A⋯Cg1ii	0.97	2.96	3.714 (5)	135

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are centroids of the C5b/C6–C9/C9a and C5a/C5b/C9a/N10/C10a rings, respectively.