(6aS,11aR,11cS)-8-Sulfanylidene-2,3,5,6,6a,7,11,11a,11b,11c-decahydro-3a,7a-diaza-1H,4H-benzo[de]anthracen-3a-ium chloride hemihydrate

Wang, L.; Zhang, C.-M.; Guo, J.-X.; Wu, Q.-Y.; Hu, H.-G.

doi:10.1107/S160053681100972X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages o1743-o1744

doi:10.1107/S160053681100972X

Open

access

(6aS,11aR,11cS)-8-Sulfanylidene-2,3,5,6,6a,7,11,11a,11b,11c-decahydro-3a,7a-diaza-1H,4H-benzo[de]anthracen-3a-ium chloride hemihydrate

Liang Wang,^a Chun-Mei Zhang,^b Jun-Xiang Guo,^b Qiu-Ye Wu ^b and Hong-Gang Hu ^b ^*

^aSchool of Pharmacy, Yantai University, Yantai 264005, People's Republic of China, and ^bDepartment of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, People's Republic of China
^*Correspondence e-mail: huhonggang_fox@msn.com

(Received 11 December 2010; accepted 15 March 2011; online 18 June 2011)

The title compound, C₁₅H₂₃N₂S⁺·Cl⁻·0.5H₂O, was prepared from (6aS,11aR,11cS)-2,3,5,6,6a,7,11,11a,11b,11c-decahydro-3a,7a-diaza-1H,4H-benzo[de]anthracene-8-one (sophocarpine) and Lawesson's reagent. The thione-substituted ring is in an envelope conformation and the three other six-membered rings are in chair conformations. In the crystal, anions and cations are linked by N—H⋯Cl and weak C—H⋯Cl hydrogen bonds. One 0.5-occupancy solvent water molecule lies on a twofold rotation axis and another 0.25-occupancy solvent water molecule is in a general position. The H atoms of these water molecules were not located or included in the refinement.

Related literature

For background to the medicinal uses of sophocarpine natural products, see: Gao et al. (2009 ); Jiang et al. (2007 ); Liu et al. (2007 ). For related structures, see: Ding et al. (2005 ); Khan et al. (1992 ). For the synthesis, see: Kaleta et al. (2006 ).

Experimental

Crystal data

C₁₅H₂₃N₂S⁺·Cl⁻·0.5H₂O
M_r = 306.87
Tetragonal, P 4₁ 2₁ 2
a = 7.793 (5) Å
c = 52.59 (5) Å
V = 3194 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.915, T_max = 0.937
11100 measured reflections
2816 independent reflections
2489 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.071
wR(F²) = 0.204
S = 1.23
2816 reflections
190 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 1023 Friedel pairs
Flack parameter: 0.1 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1	1.10 (9)	2.01 (8)	3.019 (6)	151 (6)
C4—H4A⋯Cl1ⁱ	0.97	2.82	3.726 (7)	155
Symmetry code: (i) y, x, -z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681100972X/lh5190sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100972X/lh5190Isup2.hkl

checkCIF report

Comment top

Sophocarpine ((6aS,11aR,11cS)-2,3,5,6,6a,7,11,11a,11b,11c- decahydro-1H,4H -3a,7a-diaza-βenzo[de] anthracene-8-one) and its derivatives have been found to possess a variety of pharmacological effects (Jiang et al., 2007), including anti-inflammation (Liu et al., 2007) and immunity-regulation activity (Gao et al. 2009). As part of our ongoing investigation of sophocarpine and its derivatives, we report here the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The bond lengths and angles are comparable to related structures (Khan et al., 1992; Ding et al., 2005). The C1/C2/C3/C4/C5/N2 ring is in an envelope conformation with C5 forming the flap. The three other six-membered rings A(N1/C6/C7/C8/C9/C14), B(N1/C10/C11/C12/C13/C14) and C(N2/C1/C2/C3/C4/C5) are in chair conformations. In the crystal, anions and cations are linked by N—H···Cl and weak C—H···Cl hydrogen bonds.

Related literature top

For background to the medicinal uses of sophocarpine natural products, see: Gao et al. (2009); Jiang et al. (2007); Liu et al. (2007). For related structures, see: Ding et al. (2005); Khan et al. (1992). For the synthetic procedure, see: Kaleta et al. (2006).

Experimental top

The synthetic procedure followed the methods of Kaleta et al. (2006). (6aS,11aR,11cS)-2,3,5,6,6a,7,11,11a,11b,11c-decahydro-1H, 4H-3a,7a-diaza-benzo[de] anthracene-8-one (0.01 mol) and Lawesson's reagent (0.04 mol) were mixed in toluene (100 ml) and stirred under reflux for 2 h. TLC showed that the reaction was completed. The mixture was concentrated and the residue was purified by a silica gel column. The products were stirred in dichloromethane and HCl was added. The resulting crystals were filtered and dried at room temperature. Single crystals suitable for X-ray measurements were obtained by recrystallization of a solution of the title compound in H₂O at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.

(6aS,11aR,11cS)-8-Sulfanylidene- 2,3,5,6,6a,7,11,11a,11b,11c-decahydro- 3a,7a-diaza-1H,4H-benzo[de]anthracen-3a-ium chloride hemihydrate top

Crystal data top

C₁₅H₂₃N₂S⁺·Cl⁻·0.5H₂O	D_x = 1.281 Mg m⁻³
M_r = 306.87	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₁2₁2	Cell parameters from 927 reflections
Hall symbol: P 4abw 2nw	θ = 2.7–24.0°
a = 7.793 (5) Å	µ = 0.36 mm⁻¹
c = 52.59 (5) Å	T = 293 K
V = 3194 (4) Å³	Block, yellow
Z = 8	0.25 × 0.20 × 0.18 mm
F(000) = 1320

Data collection top

Bruker SMART CCD diffractometer	2816 independent reflections
Radiation source: fine-focus sealed tube	2489 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→7
T_min = 0.915, T_max = 0.937	k = −7→9
11100 measured reflections	l = −54→62

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.071	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.204	w = 1/[σ²(F_o²) + (0.104P)² + 2.0841P] where P = (F_o² + 2F_c²)/3
S = 1.23	(Δ/σ)_max = 0.002
2816 reflections	Δρ_max = 0.64 e Å⁻³
190 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1023 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.1 (2)

Crystal data top

C₁₅H₂₃N₂S⁺·Cl⁻·0.5H₂O	Z = 8
M_r = 306.87	Mo Kα radiation
Tetragonal, P4₁2₁2	µ = 0.36 mm⁻¹
a = 7.793 (5) Å	T = 293 K
c = 52.59 (5) Å	0.25 × 0.20 × 0.18 mm
V = 3194 (4) Å³

Data collection top

Bruker SMART CCD diffractometer	2816 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2489 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.937	R_int = 0.043
11100 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.204	Δρ_max = 0.64 e Å⁻³
S = 1.23	Δρ_min = −0.25 e Å⁻³
2816 reflections	Absolute structure: Flack (1983), 1023 Friedel pairs
190 parameters	Absolute structure parameter: 0.1 (2)
0 restraints

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.6279 (2)	0.2217 (2)	0.11342 (2)	0.0559 (4)
Cl1	0.2534 (2)	0.6515 (3)	0.01987 (3)	0.0785 (6)
N1	0.4499 (5)	0.8604 (6)	0.05841 (7)	0.0415 (9)
N2	0.6084 (5)	0.4228 (5)	0.07265 (6)	0.0357 (9)
C1	0.7029 (6)	0.3215 (6)	0.08746 (8)	0.0400 (11)
C2	0.8817 (7)	0.2948 (7)	0.08006 (9)	0.0511 (12)
H2A	0.9548	0.2386	0.0913	0.061*
C3	0.9422 (7)	0.3467 (8)	0.05836 (10)	0.0543 (13)
H3A	1.0566	0.3260	0.0544	0.065*
C4	0.8319 (7)	0.4387 (7)	0.03976 (9)	0.0483 (13)
H4A	0.7864	0.3570	0.0276	0.058*
H4B	0.9011	0.5211	0.0305	0.058*
C5	0.6831 (6)	0.5324 (6)	0.05266 (7)	0.0354 (10)
H5A	0.5944	0.5540	0.0398	0.043*
C6	0.7298 (6)	0.7046 (6)	0.06520 (7)	0.0352 (10)
H6A	0.8128	0.6796	0.0787	0.042*
C7	0.8144 (7)	0.8338 (7)	0.04731 (10)	0.0482 (12)
H7A	0.8599	0.9285	0.0572	0.058*
H7B	0.9096	0.7789	0.0387	0.058*
C8	0.6899 (7)	0.9026 (7)	0.02780 (10)	0.0537 (13)
H8A	0.6499	0.8097	0.0170	0.064*
H8B	0.7472	0.9864	0.0171	0.064*
C9	0.5388 (7)	0.9856 (7)	0.04105 (10)	0.0557 (14)
H9A	0.5785	1.0832	0.0509	0.067*
H9B	0.4580	1.0271	0.0284	0.067*
C10	0.2988 (7)	0.9449 (8)	0.07086 (11)	0.0562 (15)
H10A	0.3382	1.0390	0.0814	0.067*
H10B	0.2236	0.9916	0.0579	0.067*
C11	0.2019 (7)	0.8205 (8)	0.08673 (10)	0.0558 (14)
H11A	0.1539	0.7319	0.0759	0.067*
H11B	0.1076	0.8793	0.0950	0.067*
C12	0.3168 (7)	0.7373 (8)	0.10691 (10)	0.0562 (14)
H12A	0.3504	0.8233	0.1193	0.067*
H12B	0.2523	0.6490	0.1157	0.067*
C13	0.4772 (6)	0.6578 (7)	0.09521 (8)	0.0422 (11)
H13A	0.5549	0.6309	0.1093	0.051*
C14	0.5717 (6)	0.7830 (6)	0.07802 (8)	0.0382 (11)
H14A	0.6122	0.8773	0.0888	0.046*
C15	0.4427 (6)	0.4900 (7)	0.08132 (8)	0.0394 (11)
H15A	0.3878	0.4086	0.0926	0.047*
H15B	0.3676	0.5098	0.0669	0.047*
O1	0.2960 (17)	0.2869 (17)	0.0131 (3)	0.049 (3)	0.25
O2	0.0693 (14)	0.0693 (14)	0.0000	0.179 (12)	0.50
H1	0.390 (8)	0.755 (8)	0.0486 (10)	0.066 (17)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0630 (9)	0.0610 (9)	0.0436 (6)	0.0009 (7)	−0.0016 (6)	0.0180 (6)
Cl1	0.0562 (9)	0.1312 (17)	0.0481 (7)	−0.0121 (10)	−0.0120 (7)	−0.0032 (8)
N1	0.044 (2)	0.041 (2)	0.0398 (19)	0.0012 (19)	−0.0050 (17)	0.0082 (18)
N2	0.037 (2)	0.040 (2)	0.0303 (17)	−0.0046 (17)	−0.0017 (15)	0.0024 (15)
C1	0.046 (3)	0.037 (3)	0.037 (2)	0.001 (2)	−0.006 (2)	−0.0013 (19)
C2	0.047 (3)	0.057 (3)	0.049 (3)	0.005 (3)	−0.007 (2)	0.007 (2)
C3	0.046 (3)	0.062 (4)	0.055 (3)	0.014 (3)	0.010 (2)	−0.001 (3)
C4	0.054 (3)	0.055 (3)	0.036 (2)	−0.002 (3)	0.008 (2)	−0.002 (2)
C5	0.034 (2)	0.046 (3)	0.0256 (19)	0.000 (2)	−0.0053 (17)	0.0039 (18)
C6	0.028 (2)	0.045 (3)	0.033 (2)	0.001 (2)	−0.0038 (17)	−0.0006 (19)
C7	0.041 (3)	0.048 (3)	0.056 (3)	−0.004 (2)	0.003 (2)	0.007 (2)
C8	0.056 (3)	0.052 (3)	0.052 (3)	−0.006 (3)	0.006 (2)	0.018 (2)
C9	0.056 (4)	0.048 (3)	0.064 (3)	0.002 (3)	0.000 (3)	0.021 (3)
C10	0.047 (3)	0.059 (3)	0.062 (3)	0.020 (3)	0.002 (3)	0.001 (3)
C11	0.044 (3)	0.074 (4)	0.049 (3)	0.013 (3)	0.011 (2)	0.008 (3)
C12	0.049 (3)	0.072 (4)	0.047 (3)	0.011 (3)	0.009 (2)	0.008 (3)
C13	0.038 (3)	0.056 (3)	0.032 (2)	0.003 (2)	−0.0029 (18)	0.007 (2)
C14	0.042 (3)	0.045 (3)	0.0281 (19)	0.000 (2)	−0.0086 (18)	−0.0039 (19)
C15	0.029 (2)	0.049 (3)	0.040 (2)	−0.001 (2)	−0.0022 (19)	0.012 (2)
O1	0.033 (7)	0.026 (7)	0.089 (9)	−0.006 (6)	0.007 (7)	0.002 (6)
O2	0.074 (7)	0.074 (7)	0.39 (3)	−0.027 (9)	0.080 (13)	−0.080 (13)

Geometric parameters (Å, º) top

S1—C1	1.676 (5)	C7—H7B	0.9700
N1—C10	1.499 (7)	C8—C9	1.513 (8)
N1—C9	1.505 (6)	C8—H8A	0.9700
N1—C14	1.526 (6)	C8—H8B	0.9700
N1—H1	1.07 (6)	C9—H9A	0.9700
N2—C1	1.331 (6)	C9—H9B	0.9700
N2—C15	1.466 (6)	C10—C11	1.485 (8)
N2—C5	1.474 (5)	C10—H10A	0.9700
C1—C2	1.462 (8)	C10—H10B	0.9700
C2—C3	1.299 (7)	C11—C12	1.532 (7)
C2—H2A	0.9300	C11—H11A	0.9700
C3—C4	1.486 (8)	C11—H11B	0.9700
C3—H3A	0.9300	C12—C13	1.525 (7)
C4—C5	1.529 (7)	C12—H12A	0.9700
C4—H4A	0.9700	C12—H12B	0.9700
C4—H4B	0.9700	C13—C14	1.520 (6)
C5—C6	1.539 (6)	C13—C15	1.522 (7)
C5—H5A	0.9800	C13—H13A	0.9800
C6—C7	1.527 (6)	C14—H14A	0.9800
C6—C14	1.531 (6)	C15—H15A	0.9700
C6—H6A	0.9800	C15—H15B	0.9700
C7—C8	1.511 (7)	O1—O1ⁱ	1.38 (3)
C7—H7A	0.9700

C10—N1—C9	110.0 (4)	C7—C8—H8B	109.7
C10—N1—C14	111.5 (4)	C9—C8—H8B	109.7
C9—N1—C14	112.3 (4)	H8A—C8—H8B	108.2
C10—N1—H1	102 (3)	N1—C9—C8	111.1 (4)
C9—N1—H1	114 (3)	N1—C9—H9A	109.4
C14—N1—H1	107 (3)	C8—C9—H9A	109.4
C1—N2—C15	121.2 (4)	N1—C9—H9B	109.4
C1—N2—C5	122.8 (4)	C8—C9—H9B	109.4
C15—N2—C5	111.2 (4)	H9A—C9—H9B	108.0
N2—C1—C2	117.2 (4)	C11—C10—N1	111.0 (4)
N2—C1—S1	123.9 (4)	C11—C10—H10A	109.4
C2—C1—S1	118.9 (4)	N1—C10—H10A	109.4
C3—C2—C1	122.3 (5)	C11—C10—H10B	109.4
C3—C2—H2A	118.8	N1—C10—H10B	109.4
C1—C2—H2A	118.8	H10A—C10—H10B	108.0
C2—C3—C4	121.2 (5)	C10—C11—C12	111.6 (5)
C2—C3—H3A	119.4	C10—C11—H11A	109.3
C4—C3—H3A	119.4	C12—C11—H11A	109.3
C3—C4—C5	112.1 (4)	C10—C11—H11B	109.3
C3—C4—H4A	109.2	C12—C11—H11B	109.3
C5—C4—H4A	109.2	H11A—C11—H11B	108.0
C3—C4—H4B	109.2	C13—C12—C11	111.8 (4)
C5—C4—H4B	109.2	C13—C12—H12A	109.3
H4A—C4—H4B	107.9	C11—C12—H12A	109.3
N2—C5—C4	109.8 (4)	C13—C12—H12B	109.3
N2—C5—C6	107.0 (3)	C11—C12—H12B	109.3
C4—C5—C6	115.3 (4)	H12A—C12—H12B	107.9
N2—C5—H5A	108.2	C14—C13—C15	110.6 (3)
C4—C5—H5A	108.2	C14—C13—C12	112.1 (4)
C6—C5—H5A	108.2	C15—C13—C12	113.5 (4)
C7—C6—C14	110.8 (4)	C14—C13—H13A	106.7
C7—C6—C5	114.4 (4)	C15—C13—H13A	106.7
C14—C6—C5	110.3 (4)	C12—C13—H13A	106.7
C7—C6—H6A	107.0	C13—C14—N1	110.7 (4)
C14—C6—H6A	107.0	C13—C14—C6	113.3 (4)
C5—C6—H6A	107.0	N1—C14—C6	111.1 (3)
C8—C7—C6	112.0 (4)	C13—C14—H14A	107.1
C8—C7—H7A	109.2	N1—C14—H14A	107.1
C6—C7—H7A	109.2	C6—C14—H14A	107.1
C8—C7—H7B	109.2	N2—C15—C13	107.5 (4)
C6—C7—H7B	109.2	N2—C15—H15A	110.2
H7A—C7—H7B	107.9	C13—C15—H15A	110.2
C7—C8—C9	109.8 (4)	N2—C15—H15B	110.2
C7—C8—H8A	109.7	C13—C15—H15B	110.2
C9—C8—H8A	109.7	H15A—C15—H15B	108.5

Symmetry code: (i) y, x, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	1.10 (9)	2.01 (8)	3.019 (6)	151 (6)
C4—H4A···Cl1ⁱ	0.97	2.82	3.726 (7)	155

Symmetry code: (i) y, x, −z.

Experimental details

Crystal data
Chemical formula	C₁₅H₂₃N₂S⁺·Cl⁻·0.5H₂O
M_r	306.87
Crystal system, space group	Tetragonal, P4₁2₁2
Temperature (K)	293
a, c (Å)	7.793 (5), 52.59 (5)
V (Å³)	3194 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.915, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections	11100, 2816, 2489
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.204, 1.23
No. of reflections	2816
No. of parameters	190
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.25
Absolute structure	Flack (1983), 1023 Friedel pairs
Absolute structure parameter	0.1 (2)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	1.10 (9)	2.01 (8)	3.019 (6)	151 (6)
C4—H4A···Cl1ⁱ	0.97	2.82	3.726 (7)	155

Symmetry code: (i) y, x, −z.

Acknowledgements

The authors are grateful to Weng Linhong and Dr Cheng of the Department of Chemistry of Fudan University for the data acquisition and interpretation. This work was supported by grants from the National Natural Science Foundation (No. 20902109) and the Science & Technology Commission of Shanghai Municipality (No. 08JC1405500)

References

Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ding, P. L., Liao, Z. X., Huang, H., Zhou, P. & Chen, D. F. (2005). Bioorg Med. Chem. Lett. pp. 1231–1235. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gao, Y. L., Li, G. S., Li, C. M., Zhu, X. Y., Li, M., Fu, C. L. & Li, B. F. J. (2009). Ethnopharmacology, 125, 324–329. Web of Science CrossRef PubMed CAS Google Scholar
Jiang, H., Hou, C., Zhang, S., Xie, H., Zhou, W., Jin, Q., Cheng, X., Qian, R. & Zhang, X. (2007). Eur. J. Pharmacol. 559, 98–108. Web of Science CrossRef PubMed CAS Google Scholar
Kaleta, Z., Makowski, B. T., Soos, T. & Dembinski, R. (2006). Org. Lett. 8, 1625–1628. Web of Science CrossRef PubMed CAS Google Scholar
Khan, M. A., Burrows, G. E. & Holt, E. M. (1992). Acta Cryst. C48, 2051–2053. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Liu, J. Y., Hu, J. H., Zhu, Q. G., Li, F. Q., Wang, J. & Sun, H. J. (2007). Int. Immunopharmacol. 7, 816–823. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages o1743-o1744

doi:10.1107/S160053681100972X

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(6aS,11aR,11cS)-8-Sulfanyl­idene-2,3,5,6,6a,7,11,11a,11b,11c-deca­hydro-3a,7a-di­aza-1H,4H-benzo[de]anthracen-3a-ium chloride hemihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(6aS,11aR,11cS)-8-Sulfanylidene-2,3,5,6,6a,7,11,11a,11b,11c-decahydro-3a,7a-diaza-1H,4H-benzo[de]anthracen-3a-ium chloride hemihydrate