Bis[4-(2-nitro-benzene-sulfonamido)-pyridinium] hexa-fluoro-silicate.

In the title compound, 2C(11)H(10)N(3)O(4)S(+)·SiF(6) (2-), the short C-N distance [1.386 (2) Å] is indicative of a slight conjugation of N with the π electrons of the pyridinium ring, and with those of the sulfonyl group. The dihedral angle between the benzene and pyridinium rings is 77.48 (7)°. The crystal structure is stabilized by N-H⋯F and C-H⋯F hydrogen bonds. The Si atom of the anion lies on a special position.

Related literature

For zwitterionic forms of N-aryl­benzene­sulfonamides, see: Li et al. (2007 ▶); Yu & Li (2007 ▶). For reference geometric data, see: Allen et al. (1987 ▶). Damiano et al. (2007 ▶) describe the use of pyridinium derivatives for the construction of supra­molecular architectures.

Experimental

Crystal data

2C11H10N3O4S+·SiF6 2−

M = 702.65

Monoclinic,

a = 22.691 (5) Å

b = 8.524 (2) Å

c = 14.776 (3) Å

β = 110.95 (3)°

V = 2669 (1) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 113 (2) K

0.22 × 0.16 × 0.04 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.927, T max = 0.986

10620 measured reflections

3064 independent reflections

2456 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.111

S = 1.06

3064 reflections

212 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.49 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 global, I. DOI: 10.1107/S1600536808038191/lx2077sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038191/lx2077Isup2.hkl

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

2C11H10N3O4S+·SiF62–	F000 = 1432
Mr = 702.65	Dx = 1.749 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3772 reflections
a = 22.691 (5) Å	θ = 1.9–27.5º
b = 8.524 (2) Å	µ = 0.35 mm−1
c = 14.776 (3) Å	T = 113 (2) K
β = 110.95 (3)º	Block, colourless
V = 2669 (1) Å3	0.22 × 0.16 × 0.04 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	3064 independent reflections
Radiation source: rotating anode	2456 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.053
Detector resolution: 7.31 pixels mm-1	θmax = 27.5º
T = 113(2) K	θmin = 1.9º
ω and φ scans	h = −22→29
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)	k = −10→11
Tmin = 0.927, Tmax = 0.986	l = −18→19
10620 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0513P)2 + 1.0092P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3064 reflections	Δρmax = 0.38 e Å−3
212 parameters	Δρmin = −0.49 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
S	0.61983 (2)	0.29097 (5)	0.52758 (4)	0.01969 (15)
O1	0.58452 (8)	0.32136 (18)	0.42794 (11)	0.0273 (4)
O2	0.63133 (8)	0.13308 (16)	0.56235 (12)	0.0282 (4)
O3	0.69576 (9)	0.3188 (2)	0.75056 (13)	0.0473 (5)
O4	0.78705 (10)	0.2230 (3)	0.7737 (2)	0.0843 (10)
N1	0.56160 (8)	0.8430 (2)	0.63088 (13)	0.0192 (4)
H1N	0.5583 (14)	0.942 (3)	0.639 (2)	0.052 (9)*
N2	0.58416 (9)	0.3725 (2)	0.59405 (14)	0.0194 (4)
H2N	0.5795 (14)	0.315 (3)	0.628 (2)	0.043 (9)*
N3	0.74149 (10)	0.3008 (2)	0.72703 (15)	0.0363 (5)
C1	0.57577 (9)	0.5317 (2)	0.60418 (14)	0.0167 (4)
C2	0.57532 (9)	0.6398 (2)	0.53308 (14)	0.0177 (4)
H2	0.5800	0.6058	0.4748	0.021*
C3	0.56798 (9)	0.7955 (2)	0.54852 (15)	0.0193 (4)
H3	0.5674	0.8704	0.5006	0.023*
C4	0.56074 (9)	0.7410 (2)	0.70051 (14)	0.0195 (4)
H4	0.5555	0.7784	0.7577	0.023*
C5	0.56742 (9)	0.5837 (2)	0.68832 (14)	0.0185 (4)
H5	0.5664	0.5109	0.7364	0.022*
C6	0.69299 (10)	0.3905 (2)	0.55358 (15)	0.0192 (4)
C7	0.70103 (11)	0.4743 (2)	0.47788 (16)	0.0258 (5)
H7	0.6675	0.4795	0.4169	0.031*
C8	0.75749 (12)	0.5503 (3)	0.49066 (18)	0.0309 (5)
H8	0.7620	0.6078	0.4385	0.037*
C9	0.80672 (11)	0.5435 (3)	0.57748 (19)	0.0307 (5)
H9	0.8451	0.5965	0.5854	0.037*
C10	0.80059 (10)	0.4591 (3)	0.65379 (18)	0.0295 (5)
H10	0.8347	0.4530	0.7141	0.035*
C11	0.74405 (10)	0.3839 (3)	0.64084 (16)	0.0249 (5)
Si	1.0000	0.65155 (9)	0.7500	0.01731 (19)
F1	0.94232 (7)	0.64561 (14)	0.79977 (10)	0.0303 (3)
F2	0.96119 (6)	0.51233 (14)	0.67115 (9)	0.0265 (3)
F3	0.96052 (7)	0.79039 (14)	0.67359 (9)	0.0333 (3)

	U11	U22	U33	U12	U13	U23
S	0.0207 (3)	0.0158 (3)	0.0229 (3)	−0.0010 (2)	0.0083 (2)	−0.00471 (19)
O1	0.0294 (9)	0.0304 (8)	0.0199 (8)	−0.0032 (7)	0.0060 (6)	−0.0071 (6)
O2	0.0324 (9)	0.0145 (7)	0.0426 (10)	0.0012 (7)	0.0196 (8)	−0.0020 (7)
O3	0.0360 (11)	0.0728 (14)	0.0333 (11)	0.0026 (10)	0.0127 (8)	0.0205 (10)
O4	0.0312 (11)	0.112 (2)	0.104 (2)	0.0222 (13)	0.0172 (12)	0.0855 (17)
N1	0.0217 (9)	0.0125 (8)	0.0228 (10)	0.0012 (7)	0.0073 (7)	−0.0012 (7)
N2	0.0221 (9)	0.0136 (8)	0.0242 (10)	0.0014 (7)	0.0104 (7)	0.0011 (7)
N3	0.0227 (10)	0.0443 (13)	0.0350 (12)	−0.0019 (9)	0.0019 (9)	0.0175 (10)
C1	0.0135 (9)	0.0149 (9)	0.0205 (10)	−0.0005 (8)	0.0045 (7)	−0.0011 (8)
C2	0.0195 (10)	0.0196 (10)	0.0138 (10)	0.0015 (8)	0.0060 (8)	−0.0017 (8)
C3	0.0184 (10)	0.0182 (10)	0.0195 (10)	0.0009 (8)	0.0048 (8)	0.0026 (8)
C4	0.0178 (10)	0.0244 (10)	0.0165 (10)	0.0018 (9)	0.0064 (8)	−0.0008 (8)
C5	0.0177 (10)	0.0195 (10)	0.0182 (10)	−0.0008 (8)	0.0063 (8)	0.0003 (8)
C6	0.0202 (10)	0.0168 (9)	0.0219 (11)	0.0020 (8)	0.0092 (8)	−0.0028 (8)
C7	0.0293 (12)	0.0270 (11)	0.0237 (12)	0.0011 (10)	0.0126 (9)	−0.0029 (9)
C8	0.0367 (14)	0.0297 (12)	0.0359 (14)	−0.0016 (11)	0.0247 (11)	−0.0002 (10)
C9	0.0225 (11)	0.0292 (11)	0.0457 (15)	−0.0018 (10)	0.0184 (10)	−0.0011 (11)
C10	0.0187 (11)	0.0289 (11)	0.0377 (14)	0.0019 (10)	0.0060 (9)	0.0040 (10)
C11	0.0216 (11)	0.0230 (10)	0.0295 (12)	0.0044 (9)	0.0083 (9)	0.0044 (9)
Si	0.0263 (4)	0.0132 (4)	0.0144 (4)	0.000	0.0098 (3)	0.000
F1	0.0431 (8)	0.0202 (6)	0.0393 (8)	0.0036 (6)	0.0292 (7)	0.0010 (5)
F2	0.0306 (7)	0.0222 (6)	0.0233 (7)	−0.0018 (6)	0.0056 (5)	−0.0054 (5)
F3	0.0505 (9)	0.0225 (7)	0.0248 (7)	0.0093 (6)	0.0110 (6)	0.0072 (5)

S—O1	1.426 (2)	C4—H4	0.9500
S—O2	1.431 (2)	C5—H5	0.9500
S—N2	1.634 (2)	C6—C11	1.393 (3)
S—C6	1.779 (2)	C6—C7	1.393 (3)
O3—N3	1.216 (3)	C7—C8	1.387 (3)
O4—N3	1.214 (3)	C7—H7	0.9500
N1—C3	1.338 (3)	C8—C9	1.368 (3)
N1—C4	1.353 (3)	C8—H8	0.9500
N1—H1N	0.86 (3)	C9—C10	1.385 (3)
N2—C1	1.386 (2)	C9—H9	0.9500
N2—H2N	0.73 (3)	C10—C11	1.385 (3)
N3—C11	1.477 (3)	C10—H10	0.9500
C1—C2	1.395 (3)	Si—F3i	1.6597 (14)
C1—C5	1.395 (3)	Si—F3	1.6597 (14)
C2—C3	1.367 (3)	Si—F2	1.6756 (13)
C2—H2	0.9500	Si—F2i	1.6756 (13)
C3—H3	0.9500	Si—F1i	1.7161 (13)
C4—C5	1.368 (3)	Si—F1	1.7161 (13)
O1—S—O2	120.30 (10)	C7—C6—S	116.81 (16)
O1—S—N2	109.10 (10)	C8—C7—C6	120.7 (2)
O2—S—N2	104.47 (10)	C8—C7—H7	119.7
O1—S—C6	105.83 (10)	C6—C7—H7	119.7
O2—S—C6	109.54 (10)	C9—C8—C7	120.8 (2)
N2—S—C6	106.98 (10)	C9—C8—H8	119.6
C3—N1—C4	122.20 (18)	C7—C8—H8	119.6
C3—N1—H1N	118 (2)	C8—C9—C10	119.9 (2)
C4—N1—H1N	120 (2)	C8—C9—H9	120.0
C1—N2—S	126.70 (16)	C10—C9—H9	120.0
C1—N2—H2N	122 (2)	C11—C10—C9	119.0 (2)
S—N2—H2N	110 (2)	C11—C10—H10	120.5
O4—N3—O3	123.2 (2)	C9—C10—H10	120.5
O4—N3—C11	117.7 (2)	C10—C11—C6	122.2 (2)
O3—N3—C11	119.09 (19)	C10—C11—N3	115.0 (2)
N2—C1—C2	122.01 (19)	C6—C11—N3	122.8 (2)
N2—C1—C5	118.34 (18)	F3i—Si—F3	89.03 (10)
C2—C1—C5	119.64 (18)	F3i—Si—F2	178.59 (7)
C3—C2—C1	118.97 (19)	F3—Si—F2	90.59 (7)
C3—C2—H2	120.5	F3i—Si—F2i	90.59 (7)
C1—C2—H2	120.5	F3—Si—F2i	178.59 (7)
N1—C3—C2	120.30 (19)	F2—Si—F2i	89.82 (9)
N1—C3—H3	119.8	F3i—Si—F1i	90.21 (7)
C2—C3—H3	119.8	F3—Si—F1i	92.20 (7)
N1—C4—C5	119.82 (19)	F2—Si—F1i	88.45 (7)
N1—C4—H4	120.1	F2i—Si—F1i	89.16 (7)
C5—C4—H4	120.1	F3i—Si—F1	92.20 (7)
C4—C5—C1	119.02 (19)	F3—Si—F1	90.21 (7)
C4—C5—H5	120.5	F2—Si—F1	89.16 (7)
C1—C5—H5	120.5	F2i—Si—F1	88.45 (7)
C11—C6—C7	117.3 (2)	F1i—Si—F1	176.62 (9)
C11—C6—S	125.73 (17)
O1—S—N2—C1	−65.8 (2)	O2—S—C6—C7	131.78 (16)
O2—S—N2—C1	164.31 (18)	N2—S—C6—C7	−115.54 (17)
C6—S—N2—C1	48.2 (2)	C11—C6—C7—C8	−1.3 (3)
S—N2—C1—C2	24.9 (3)	S—C6—C7—C8	−177.48 (17)
S—N2—C1—C5	−155.30 (16)	C6—C7—C8—C9	0.6 (3)
N2—C1—C2—C3	−178.80 (19)	C7—C8—C9—C10	0.4 (3)
C5—C1—C2—C3	1.4 (3)	C8—C9—C10—C11	−0.6 (3)
C4—N1—C3—C2	−1.5 (3)	C9—C10—C11—C6	−0.1 (3)
C1—C2—C3—N1	0.3 (3)	C9—C10—C11—N3	−178.4 (2)
C3—N1—C4—C5	0.9 (3)	C7—C6—C11—C10	1.0 (3)
N1—C4—C5—C1	0.7 (3)	S—C6—C11—C10	176.86 (17)
N2—C1—C5—C4	178.30 (18)	C7—C6—C11—N3	179.2 (2)
C2—C1—C5—C4	−1.9 (3)	S—C6—C11—N3	−5.0 (3)
O1—S—C6—C11	−175.15 (18)	O4—N3—C11—C10	−43.6 (3)
O2—S—C6—C11	−44.1 (2)	O3—N3—C11—C10	132.9 (2)
N2—S—C6—C11	68.6 (2)	O4—N3—C11—C6	138.1 (3)
O1—S—C6—C7	0.70 (18)	O3—N3—C11—C6	−45.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···F1ii	0.86 (3)	1.96 (3)	2.789 (2)	162 (3)
N2—H2N···F1iii	0.73 (3)	1.97 (3)	2.690 (2)	171 (3)
C4—H4···F2ii	0.95	2.35	3.141 (2)	141
C5—H5···F3iii	0.95	2.50	3.426 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯F1i	0.86 (3)	1.96 (3)	2.789 (2)	162 (3)
N2—H2N⋯F1ii	0.73 (3)	1.97 (3)	2.690 (2)	171 (3)
C4—H4⋯F2i	0.95	2.35	3.141 (2)	141
C5—H5⋯F3ii	0.95	2.50	3.426 (3)	165

Symmetry codes: (i) ; (ii) .