(7aR*,12bS*)-8,12b-Dihydro-7aH-indeno-[1',2':5,6][1,4]selenazino[2,3,4-ij]quinolin-13-ium hydrogen sulfate.

In the title compound, C(18)H(14)NSe(+)·HSO(4) (-), the cyclo-pentene ring in the cation has an envelope conformation while the central six-membered 1,4-selenazine ring adopts a sofa conformation. The dihedral angle between the planes of the terminal benzene rings is 68.08 (11)°. In the crystal, the anions form chains along the c axis through O-H⋯O hydrogen bonds. Weak C-H⋯O and C-H⋯π hydrogen bonds, as well as attractive Se⋯Se [3.5608 (8) Å] inter-actions, further consolidate the crystal structure.

Related literature

For the synthesis and biological properties of selenium- and nitro­gen-containing heterocycles, see: Mugesh et al. (2001 ▶); Koketsu & Ishihara (2003 ▶); Nogueira et al. (2004 ▶); Bhabak & Mugesh (2007 ▶); Mlochowski & Giurg (2009 ▶); Back (2009 ▶); Mukherjee et al. (2010 ▶). For related compounds, see: Wright (2001 ▶); Garud et al. (2007 ▶); Sommen et al. (2007 ▶); Borisov et al. (2011 ▶).

Experimental

Crystal data

C18H14NSe+·HSO4 −

M = 420.34

Monoclinic,

a = 11.1355 (11) Å

b = 19.5653 (19) Å

c = 7.9609 (8) Å

β = 107.005 (2)°

V = 1658.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.41 mm−1

T = 120 K

0.20 × 0.02 × 0.02 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.644, T max = 0.953

14396 measured reflections

4007 independent reflections

2902 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.114

S = 1.00

4007 reflections

226 parameters

H-atom parameters constrained

Δρmax = 1.00 e Å−3

Δρmin = −0.51 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811047167/rk2313sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047167/rk2313Isup2.hkl

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

C18H14NSe+·HSO4−	F(000) = 848
Mr = 420.34	Dx = 1.683 Mg m−3
Monoclinic, P21/c	Melting point = 502–503 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.1355 (11) Å	Cell parameters from 2341 reflections
b = 19.5653 (19) Å	θ = 2.2–24.8°
c = 7.9609 (8) Å	µ = 2.41 mm−1
β = 107.005 (2)°	T = 120 K
V = 1658.6 (3) Å3	Needle, orange
Z = 4	0.20 × 0.02 × 0.02 mm

Bruker SMART 1K CCD diffractometer	4007 independent reflections
Radiation source: fine-focus sealed tube	2902 reflections with I > 2σ(I)
graphite	Rint = 0.054
φ and ω scans	θmax = 28.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −14→14
Tmin = 0.644, Tmax = 0.953	k = −24→25
14396 measured reflections	l = −10→10

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)] = 0.044	Hydrogen site location: difference Fourier map
wR(F2) = 0.114	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.054P)2 + 2.36P] where P = (Fo2 + 2Fc2)/3
4007 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 1.00 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.1870 (3)	0.58708 (18)	0.3376 (5)	0.0216 (7)
H1	0.2013	0.6277	0.4059	0.026*
C2	0.1119 (3)	0.53643 (18)	0.3759 (5)	0.0242 (8)
H2	0.0772	0.5420	0.4708	0.029*
C3	0.0884 (3)	0.47893 (19)	0.2765 (5)	0.0236 (7)
H3	0.0365	0.4441	0.3010	0.028*
C3A	0.1413 (3)	0.47090 (17)	0.1365 (4)	0.0183 (7)
C4	0.1189 (3)	0.40994 (19)	0.0350 (5)	0.0227 (7)
H4	0.0648	0.3756	0.0564	0.027*
C5	0.1763 (3)	0.40145 (19)	−0.0938 (5)	0.0246 (8)
H5	0.1622	0.3608	−0.1621	0.030*
C6	0.2556 (3)	0.45222 (19)	−0.1259 (4)	0.0224 (7)
H6	0.2938	0.4452	−0.2167	0.027*
C6A	0.2801 (3)	0.51193 (17)	−0.0303 (4)	0.0192 (7)
Se7	0.40049 (3)	0.571862 (19)	−0.07394 (4)	0.02345 (12)
C7A	0.3453 (3)	0.65434 (18)	0.0190 (4)	0.0218 (7)
H7A	0.2719	0.6763	−0.0679	0.026*
C8	0.4599 (3)	0.70229 (18)	0.0743 (4)	0.0242 (8)
H8A	0.5125	0.6978	−0.0061	0.029*
H8B	0.4334	0.7505	0.0757	0.029*
C8A	0.5298 (3)	0.67800 (17)	0.2574 (4)	0.0208 (7)
C9	0.6519 (3)	0.69027 (18)	0.3579 (5)	0.0237 (7)
H9	0.7065	0.7171	0.3129	0.028*
C10	0.6934 (3)	0.6625 (2)	0.5264 (5)	0.0274 (8)
H10	0.7772	0.6704	0.5967	0.033*
C11	0.6130 (3)	0.6235 (2)	0.5921 (5)	0.0274 (8)
H11	0.6426	0.6048	0.7070	0.033*
C12	0.4901 (3)	0.61157 (18)	0.4919 (4)	0.0215 (7)
H12	0.4349	0.5851	0.5369	0.026*
C12A	0.4499 (3)	0.63916 (16)	0.3249 (4)	0.0164 (6)
C12B	0.3200 (3)	0.64029 (17)	0.1943 (4)	0.0182 (7)
H12B	0.2770	0.6818	0.2221	0.022*
N13	0.2398 (2)	0.58057 (13)	0.2079 (3)	0.0155 (5)
C13A	0.2219 (3)	0.52230 (17)	0.1038 (4)	0.0165 (6)
S1	0.07534 (8)	0.71231 (4)	0.61913 (10)	0.01767 (18)
O1	0.1979 (2)	0.70926 (12)	0.5924 (3)	0.0217 (5)
O2	0.0535 (2)	0.66144 (13)	0.7377 (3)	0.0268 (6)
O3	0.0469 (2)	0.78149 (12)	0.6674 (3)	0.0232 (5)
O4	−0.0231 (2)	0.69555 (14)	0.4394 (3)	0.0290 (6)
H4O	0.0104	0.7065	0.3440	0.043*

	U11	U22	U33	U12	U13	U23
C1	0.0230 (17)	0.0187 (18)	0.0244 (17)	0.0016 (14)	0.0093 (14)	−0.0044 (13)
C2	0.0268 (18)	0.025 (2)	0.0273 (18)	−0.0002 (15)	0.0177 (15)	−0.0031 (14)
C3	0.0234 (17)	0.0207 (18)	0.0289 (18)	−0.0007 (14)	0.0111 (15)	0.0006 (14)
C3A	0.0149 (15)	0.0174 (17)	0.0213 (16)	0.0016 (13)	0.0034 (13)	−0.0001 (13)
C4	0.0169 (16)	0.0240 (19)	0.0252 (17)	−0.0037 (14)	0.0028 (14)	−0.0028 (14)
C5	0.0223 (18)	0.0213 (18)	0.0274 (18)	−0.0050 (14)	0.0028 (15)	−0.0100 (14)
C6	0.0197 (17)	0.0265 (19)	0.0206 (16)	0.0021 (15)	0.0052 (14)	−0.0053 (14)
C6A	0.0184 (16)	0.0206 (18)	0.0184 (15)	−0.0026 (13)	0.0049 (13)	−0.0009 (13)
Se7	0.0276 (2)	0.0244 (2)	0.02247 (19)	−0.00505 (15)	0.01375 (14)	−0.00375 (14)
C7A	0.0265 (18)	0.0193 (18)	0.0191 (16)	0.0015 (14)	0.0059 (14)	0.0041 (13)
C8	0.032 (2)	0.0197 (18)	0.0226 (17)	−0.0019 (15)	0.0101 (15)	0.0031 (14)
C8A	0.0270 (18)	0.0117 (16)	0.0262 (17)	0.0012 (14)	0.0119 (15)	−0.0013 (13)
C9	0.0201 (17)	0.0204 (18)	0.0335 (19)	−0.0041 (14)	0.0122 (15)	−0.0062 (15)
C10	0.0180 (17)	0.034 (2)	0.0269 (18)	0.0022 (15)	0.0015 (14)	−0.0095 (16)
C11	0.0248 (19)	0.029 (2)	0.0254 (18)	0.0051 (16)	0.0026 (15)	0.0003 (15)
C12	0.0204 (17)	0.0222 (18)	0.0214 (16)	0.0024 (14)	0.0055 (13)	0.0022 (14)
C12A	0.0169 (15)	0.0141 (16)	0.0179 (15)	0.0012 (13)	0.0046 (12)	−0.0031 (12)
C12B	0.0186 (16)	0.0150 (16)	0.0195 (16)	−0.0001 (13)	0.0034 (13)	0.0009 (13)
N13	0.0144 (13)	0.0135 (14)	0.0190 (13)	0.0012 (10)	0.0056 (10)	0.0001 (10)
C13A	0.0126 (14)	0.0155 (16)	0.0188 (15)	0.0018 (12)	0.0007 (12)	−0.0017 (12)
S1	0.0187 (4)	0.0188 (4)	0.0159 (4)	−0.0036 (3)	0.0057 (3)	−0.0017 (3)
O1	0.0203 (12)	0.0209 (13)	0.0244 (12)	−0.0030 (10)	0.0074 (10)	−0.0040 (10)
O2	0.0313 (14)	0.0236 (14)	0.0261 (13)	−0.0067 (11)	0.0095 (11)	0.0032 (10)
O3	0.0317 (14)	0.0212 (13)	0.0189 (11)	0.0032 (11)	0.0107 (10)	0.0012 (10)
O4	0.0227 (13)	0.0483 (17)	0.0163 (12)	−0.0130 (12)	0.0064 (10)	−0.0072 (11)

C1—N13	1.336 (4)	C8—H8A	0.9900
C1—C2	1.386 (5)	C8—H8B	0.9900
C1—H1	0.9500	C8A—C9	1.382 (5)
C2—C3	1.356 (5)	C8A—C12A	1.391 (4)
C2—H2	0.9500	C9—C10	1.395 (5)
C3—C3A	1.414 (5)	C9—H9	0.9500
C3—H3	0.9500	C10—C11	1.390 (5)
C3A—C4	1.421 (5)	C10—H10	0.9500
C3A—C13A	1.422 (5)	C11—C12	1.388 (5)
C4—C5	1.368 (5)	C11—H11	0.9500
C4—H4	0.9500	C12—C12A	1.383 (5)
C5—C6	1.401 (5)	C12—H12	0.9500
C5—H5	0.9500	C12A—C12B	1.515 (4)
C6—C6A	1.377 (5)	C12B—N13	1.494 (4)
C6—H6	0.9500	C12B—H12B	1.0000
C6A—C13A	1.416 (4)	N13—C13A	1.389 (4)
C6A—Se7	1.888 (3)	S1—O2	1.441 (2)
Se7—C7A	1.948 (3)	S1—O1	1.443 (2)
C7A—C12B	1.527 (4)	S1—O3	1.467 (2)
C7A—C8	1.541 (5)	S1—O4	1.562 (2)
C7A—H7A	1.0000	O4—H4O	0.9632
C8—C8A	1.514 (5)
N13—C1—C2	122.1 (3)	C9—C8A—C12A	120.2 (3)
N13—C1—H1	118.9	C9—C8A—C8	130.1 (3)
C2—C1—H1	118.9	C12A—C8A—C8	109.7 (3)
C3—C2—C1	119.4 (3)	C8A—C9—C10	118.8 (3)
C3—C2—H2	120.3	C8A—C9—H9	120.6
C1—C2—H2	120.3	C10—C9—H9	120.6
C2—C3—C3A	119.9 (3)	C11—C10—C9	120.5 (3)
C2—C3—H3	120.1	C11—C10—H10	119.8
C3A—C3—H3	120.1	C9—C10—H10	119.8
C3—C3A—C4	119.8 (3)	C12—C11—C10	120.8 (3)
C3—C3A—C13A	119.8 (3)	C12—C11—H11	119.6
C4—C3A—C13A	120.3 (3)	C10—C11—H11	119.6
C5—C4—C3A	119.0 (3)	C12A—C12—C11	118.3 (3)
C5—C4—H4	120.5	C12A—C12—H12	120.8
C3A—C4—H4	120.5	C11—C12—H12	120.8
C4—C5—C6	120.5 (3)	C12—C12A—C8A	121.4 (3)
C4—C5—H5	119.7	C12—C12A—C12B	129.9 (3)
C6—C5—H5	119.7	C8A—C12A—C12B	108.5 (3)
C6A—C6—C5	122.3 (3)	N13—C12B—C12A	114.2 (3)
C6A—C6—H6	118.8	N13—C12B—C7A	118.7 (3)
C5—C6—H6	118.8	C12A—C12B—C7A	103.6 (3)
C6—C6A—C13A	118.5 (3)	N13—C12B—H12B	106.5
C6—C6A—Se7	117.5 (3)	C12A—C12B—H12B	106.5
C13A—C6A—Se7	123.8 (2)	C7A—C12B—H12B	106.5
C6A—Se7—C7A	97.16 (15)	C1—N13—C13A	121.4 (3)
C12B—C7A—C8	102.0 (3)	C1—N13—C12B	112.9 (3)
C12B—C7A—Se7	111.2 (2)	C13A—N13—C12B	125.7 (3)
C8—C7A—Se7	106.6 (2)	N13—C13A—C6A	123.4 (3)
C12B—C7A—H7A	112.2	N13—C13A—C3A	117.3 (3)
C8—C7A—H7A	112.2	C6A—C13A—C3A	119.3 (3)
Se7—C7A—H7A	112.2	O2—S1—O1	114.60 (15)
C8A—C8—C7A	103.5 (3)	O2—S1—O3	112.03 (15)
C8A—C8—H8A	111.1	O1—S1—O3	111.29 (15)
C7A—C8—H8A	111.1	O2—S1—O4	104.34 (15)
C8A—C8—H8B	111.1	O1—S1—O4	107.28 (14)
C7A—C8—H8B	111.1	O3—S1—O4	106.62 (15)
H8A—C8—H8B	109.0	S1—O4—H4O	110.2
N13—C1—C2—C3	−1.6 (5)	C8—C8A—C12A—C12B	−4.2 (4)
C1—C2—C3—C3A	0.6 (5)	C12—C12A—C12B—N13	−30.0 (5)
C2—C3—C3A—C4	178.6 (3)	C8A—C12A—C12B—N13	155.7 (3)
C2—C3—C3A—C13A	1.9 (5)	C12—C12A—C12B—C7A	−160.7 (3)
C3—C3A—C4—C5	−176.5 (3)	C8A—C12A—C12B—C7A	25.1 (3)
C13A—C3A—C4—C5	0.2 (5)	C8—C7A—C12B—N13	−162.7 (3)
C3A—C4—C5—C6	−0.3 (5)	Se7—C7A—C12B—N13	−49.4 (4)
C4—C5—C6—C6A	0.4 (5)	C8—C7A—C12B—C12A	−34.8 (3)
C5—C6—C6A—C13A	−0.5 (5)	Se7—C7A—C12B—C12A	78.5 (3)
C5—C6—C6A—Se7	174.4 (3)	C2—C1—N13—C13A	0.1 (5)
C6—C6A—Se7—C7A	159.0 (3)	C2—C1—N13—C12B	−178.1 (3)
C13A—C6A—Se7—C7A	−26.4 (3)	C12A—C12B—N13—C1	80.4 (3)
C6A—Se7—C7A—C12B	44.9 (3)	C7A—C12B—N13—C1	−156.9 (3)
C6A—Se7—C7A—C8	155.2 (2)	C12A—C12B—N13—C13A	−97.7 (4)
C12B—C7A—C8—C8A	32.3 (3)	C7A—C12B—N13—C13A	25.0 (4)
Se7—C7A—C8—C8A	−84.4 (3)	C1—N13—C13A—C6A	−177.3 (3)
C7A—C8—C8A—C9	163.5 (3)	C12B—N13—C13A—C6A	0.6 (5)
C7A—C8—C8A—C12A	−18.1 (4)	C1—N13—C13A—C3A	2.3 (4)
C12A—C8A—C9—C10	0.6 (5)	C12B—N13—C13A—C3A	−179.7 (3)
C8—C8A—C9—C10	178.8 (3)	C6—C6A—C13A—N13	−179.9 (3)
C8A—C9—C10—C11	−0.3 (5)	Se7—C6A—C13A—N13	5.5 (5)
C9—C10—C11—C12	−0.2 (6)	C6—C6A—C13A—C3A	0.5 (5)
C10—C11—C12—C12A	0.3 (5)	Se7—C6A—C13A—C3A	−174.2 (2)
C11—C12—C12A—C8A	0.0 (5)	C3—C3A—C13A—N13	−3.3 (5)
C11—C12—C12A—C12B	−173.6 (3)	C4—C3A—C13A—N13	−179.9 (3)
C9—C8A—C12A—C12	−0.5 (5)	C3—C3A—C13A—C6A	176.4 (3)
C8—C8A—C12A—C12	−179.0 (3)	C4—C3A—C13A—C6A	−0.3 (5)
C9—C8A—C12A—C12B	174.4 (3)

Cg is the centroid of the C3A/C4–C6/C6A/C13A ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O3i	0.96	1.59	2.548 (3)	171
C1—H1···O1	0.95	2.19	3.114 (4)	165
C3—H3···O2ii	0.95	2.28	3.154 (4)	153
C4—H4···O2ii	0.95	2.49	3.308 (4)	144
C5—H5···O4iii	0.95	2.55	3.367 (4)	145
C7A—H7A···O2iv	1.00	2.49	3.367 (4)	146
C12B—H12B···O1i	1.00	2.42	3.244 (4)	139
C12B—H12B···O3i	1.00	2.57	3.355 (4)	135
C11—H11···Cgv	0.95	2.78	3.679 (4)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C3A/C4–C6/C6A/C13A ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O3i	0.96	1.59	2.548 (3)	171
C1—H1⋯O1	0.95	2.19	3.114 (4)	165
C3—H3⋯O2ii	0.95	2.28	3.154 (4)	153
C4—H4⋯O2ii	0.95	2.49	3.308 (4)	144
C5—H5⋯O4iii	0.95	2.55	3.367 (4)	145
C7A—H7A⋯O2iv	1.00	2.49	3.367 (4)	146
C12B—H12B⋯O1i	1.00	2.42	3.244 (4)	139
C12B—H12B⋯O3i	1.00	2.57	3.355 (4)	135
C11—H11⋯Cgv	0.95	2.78	3.679 (4)	159

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