Bis[5-oxo-4,5-dihydro-8H-2-azonia-4,8,9-trizabicyclo[4.3.0]nona-2,6,9(1)-triene] sulfate.

In the crystal structure of the title compound, 2C(5)H(5)N(4)O(+)·SO(4) (2-), N-H⋯O hydrogen bonds assemble the mol-ecules into a two-dimensional network structure parallel to the cb plane. The S atom of the sulfate ion lies on a special position on a twofold axis.

Related literature

For general background, see: Elion et al. (1962 ▶); Rundles et al. (1966 ▶). For related structures, see: Prusiner & Sundaralingam (1972 ▶); Gadret et al. (1974 ▶); Sheldrick & Bell (1987 ▶); Singh & Pedersen (1993 ▶).

Experimental

Crystal data

2C5H5N4O+·SO4 2−

M = 370.32

Monoclinic,

a = 12.337 (3) Å

b = 10.054 (2) Å

c = 11.064 (2) Å

β = 102.42 (3)°

V = 1340.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 298 (2) K

0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

3561 measured reflections

1323 independent reflections

1252 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.096

S = 1.05

1323 reflections

132 parameters

All H-atom parameters refined

Δρmax = 0.32 e Å−3

Δρmin = −0.38 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038026/gw2054sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038026/gw2054Isup2.hkl

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

2C5H5N4O+·S1O42–	F000 = 760
Mr = 370.32	Dx = 1.835 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1323 reflections
a = 12.337 (3) Å	θ = 2.6–26.1º
b = 10.054 (2) Å	µ = 0.30 mm−1
c = 11.064 (2) Å	T = 298 (2) K
β = 102.42 (3)º	Plate, colourless
V = 1340.2 (5) Å3	0.20 × 0.20 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1252 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Monochromator: graphite	θmax = 26.1º
T = 298(2) K	θmin = 2.6º
φ and ω scans	h = −15→11
Absorption correction: none	k = −10→12
3561 measured reflections	l = −13→13
1323 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.035	w = 1/[σ2(Fo2) + (0.0621P)2 + 0.9856P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.32 e Å−3
1323 reflections	Δρmin = −0.38 e Å−3
132 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0068 (13)
Secondary atom site location: difference Fourier map

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	0.5000	0.24338 (5)	0.2500	0.0248 (2)
O3	0.41241 (12)	0.33107 (12)	0.17777 (11)	0.0458 (4)
O2	0.45510 (13)	0.16122 (14)	0.33449 (12)	0.0472 (4)
O1	0.32972 (10)	0.07703 (11)	0.91973 (10)	0.0354 (3)
N1	0.35100 (11)	0.30200 (13)	0.92837 (12)	0.0279 (3)
C4	0.35629 (12)	0.19500 (15)	0.73986 (13)	0.0244 (3)
N3	0.38403 (11)	0.18821 (14)	0.55266 (13)	0.0289 (3)
N4	0.38369 (11)	0.32129 (13)	0.57759 (12)	0.0290 (3)
N2	0.36693 (11)	0.43601 (13)	0.76273 (12)	0.0281 (3)
C1	0.34391 (12)	0.17773 (15)	0.86560 (14)	0.0254 (3)
C3	0.36700 (12)	0.32242 (14)	0.69190 (14)	0.0245 (3)
C5	0.36919 (13)	0.11072 (16)	0.64455 (14)	0.0275 (3)
C2	0.36240 (13)	0.41996 (16)	0.87928 (14)	0.0287 (4)
H2	0.3674 (16)	0.4935 (19)	0.9297 (18)	0.033 (5)*
H4	0.3710 (16)	0.018 (2)	0.6442 (18)	0.036 (5)*
H3	0.3781 (18)	0.522 (2)	0.735 (2)	0.049 (6)*
H5	0.3967 (18)	0.168 (2)	0.485 (2)	0.045 (6)*
H1	0.3606 (18)	0.299 (2)	1.012 (2)	0.044 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.0361 (3)	0.0221 (3)	0.0175 (3)	0.000	0.0085 (2)	0.000
O3	0.0595 (8)	0.0395 (7)	0.0306 (6)	0.0168 (6)	−0.0078 (6)	−0.0102 (5)
O2	0.0712 (9)	0.0445 (8)	0.0339 (7)	−0.0155 (7)	0.0293 (7)	−0.0026 (6)
O1	0.0502 (7)	0.0289 (6)	0.0290 (6)	−0.0007 (5)	0.0131 (5)	0.0064 (5)
N1	0.0360 (7)	0.0293 (7)	0.0196 (7)	0.0007 (5)	0.0085 (5)	−0.0018 (5)
C4	0.0280 (7)	0.0244 (8)	0.0212 (7)	−0.0003 (5)	0.0063 (6)	−0.0002 (5)
N3	0.0348 (7)	0.0323 (8)	0.0208 (6)	0.0000 (5)	0.0088 (5)	−0.0051 (5)
N4	0.0354 (7)	0.0306 (7)	0.0220 (7)	0.0002 (5)	0.0081 (5)	0.0016 (5)
N2	0.0372 (7)	0.0218 (7)	0.0256 (7)	0.0006 (5)	0.0075 (5)	0.0001 (5)
C1	0.0268 (7)	0.0279 (8)	0.0220 (7)	0.0008 (6)	0.0065 (6)	−0.0001 (5)
C3	0.0267 (7)	0.0259 (8)	0.0209 (7)	0.0008 (5)	0.0051 (6)	−0.0011 (5)
C5	0.0320 (8)	0.0264 (8)	0.0246 (7)	−0.0005 (6)	0.0071 (6)	−0.0044 (6)
C2	0.0333 (8)	0.0273 (8)	0.0251 (7)	0.0017 (6)	0.0056 (6)	−0.0052 (6)

S1—O2i	1.4442 (12)	C4—C1	1.442 (2)
S1—O2	1.4443 (12)	N3—C5	1.324 (2)
S1—O3	1.4873 (13)	N3—N4	1.366 (2)
S1—O3i	1.4873 (13)	N3—H5	0.82 (2)
O1—C1	1.2081 (18)	N4—C3	1.324 (2)
N1—C2	1.324 (2)	N2—C2	1.313 (2)
N1—C1	1.423 (2)	N2—C3	1.3851 (19)
N1—H1	0.91 (2)	N2—H3	0.94 (2)
C4—C5	1.388 (2)	C5—H4	0.94 (2)
C4—C3	1.404 (2)	C2—H2	0.92 (2)
O2i—S1—O2	110.23 (11)	C2—N2—C3	117.38 (13)
O2i—S1—O3	109.07 (8)	C2—N2—H3	118.7 (13)
O2—S1—O3	110.57 (9)	C3—N2—H3	123.5 (13)
O2i—S1—O3i	110.57 (9)	O1—C1—N1	119.61 (14)
O2—S1—O3i	109.07 (8)	O1—C1—C4	129.47 (14)
O3—S1—O3i	107.30 (11)	N1—C1—C4	110.91 (13)
C2—N1—C1	125.94 (13)	N4—C3—N2	124.51 (14)
C2—N1—H1	116.4 (14)	N4—C3—C4	113.56 (13)
C1—N1—H1	116.7 (14)	N2—C3—C4	121.80 (13)
C5—C4—C3	103.56 (13)	N3—C5—C4	106.34 (14)
C5—C4—C1	135.43 (14)	N3—C5—H4	125.2 (12)
C3—C4—C1	120.84 (13)	C4—C5—H4	128.4 (12)
C5—N3—N4	114.47 (13)	N2—C2—N1	122.93 (14)
C5—N3—H5	129.3 (15)	N2—C2—H2	119.1 (12)
N4—N3—H5	116.1 (15)	N1—C2—H2	118.0 (12)
C3—N4—N3	102.07 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H3···O3ii	0.936 (10)	1.698 (14)	2.628 (2)	173 (3)
N3—H5···O2	0.819 (10)	1.957 (18)	2.753 (3)	164 (3)
N1—H1···O3iii	0.906 (10)	1.838 (13)	2.716 (3)	163 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H3⋯O3i	0.936 (10)	1.698 (14)	2.628 (2)	173 (3)
N3—H5⋯O2	0.819 (10)	1.957 (18)	2.753 (3)	164 (3)
N1—H1⋯O3ii	0.906 (10)	1.838 (13)	2.716 (3)	163 (3)

Symmetry codes: (i) ; (ii) .