4-(4-Nitro-benzene-sulfonamido)pyridinium nitrate.

A short C-N distance [1.394 (2) Å] in the title compound, C(11)H(10)N(3)O(4)S(+)·NO(3) (-), is indicative of some conjugation of the sulfonamide π electrons with those of the pyridinium ring. The crystal structure is stabilized by N-H⋯O hydrogen bonds.

Related literature

For zwitterionic forms of N-aryl­benzene­sulfonamides, see: Li et al. (2007 ▶); Yu & Li (2007 ▶). For reference geometrical 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

C11H10N3O4S+·NO3 −

M = 342.29

Monoclinic,

a = 36.516 (7) Å

b = 5.3742 (11) Å

c = 13.964 (3) Å

β = 99.54 (3)°

V = 2702.5 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 113 (2) K

0.20 × 0.12 × 0.04 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.94, T max = 0.99

11804 measured reflections

3203 independent reflections

2648 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.107

S = 1.09

3203 reflections

216 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.41 e Å−3

Data collection: CrystalClear (Rigaku, 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/S160053680803883X/bg2225sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803883X/bg2225Isup2.hkl

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

C11H10N3O4S+·NO3–	F000 = 1408
Mr = 342.29	Dx = 1.683 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4207 reflections
a = 36.516 (7) Å	θ = 2.3–27.9º
b = 5.3742 (11) Å	µ = 0.29 mm−1
c = 13.964 (3) Å	T = 113 (2) K
β = 99.54 (3)º	Block, colorless
V = 2702.5 (10) Å3	0.20 × 0.12 × 0.04 mm
Z = 8

Rigaku Saturn CCD area-detector diffractometer	3203 independent reflections
Radiation source: Rotating anode	2648 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.037
Detector resolution: 7.31 pixels mm-1	θmax = 27.9º
T = 113(2) K	θmin = 2.3º
ω and φ scans	h = −47→46
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −7→7
Tmin = 0.94, Tmax = 0.99	l = −14→18
11804 measured reflections

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0612P)2 + 0.5371P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
3203 reflections	Δρmax = 0.30 e Å−3
216 parameters	Δρmin = −0.41 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.133115 (11)	0.62515 (7)	0.45086 (3)	0.01800 (13)
O1	0.12702 (3)	0.8195 (2)	0.51613 (8)	0.0246 (3)
O2	0.14580 (3)	0.6801 (2)	0.36175 (8)	0.0256 (3)
O3	0.25592 (4)	−0.2298 (3)	0.63494 (9)	0.0323 (3)
O4	0.22026 (4)	−0.2269 (2)	0.74432 (8)	0.0285 (3)
N1	0.06215 (5)	−0.1019 (3)	0.23971 (11)	0.0287 (4)
N2	0.09333 (4)	0.4790 (2)	0.42774 (10)	0.0167 (3)
N3	0.22946 (4)	−0.1490 (3)	0.66941 (10)	0.0211 (3)
C1	0.08430 (4)	0.2815 (3)	0.36372 (10)	0.0158 (3)
C2	0.05600 (4)	0.1211 (3)	0.38117 (11)	0.0186 (3)
H2A	0.0441	0.1453	0.4361	0.022*
C3	0.04565 (5)	−0.0704 (3)	0.31855 (12)	0.0259 (4)
H3	0.0268	−0.1822	0.3304	0.031*
C4	0.08911 (5)	0.0488 (3)	0.22111 (12)	0.0280 (4)
H4	0.1000	0.0222	0.1648	0.034*
C5	0.10119 (5)	0.2409 (3)	0.28211 (11)	0.0223 (4)
H5	0.1208	0.3456	0.2694	0.027*
C6	0.16389 (4)	0.4066 (3)	0.51584 (11)	0.0170 (3)
C7	0.18870 (5)	0.2755 (3)	0.46944 (11)	0.0199 (3)
H7	0.1905	0.3098	0.4037	0.024*
C8	0.21072 (5)	0.0943 (3)	0.52069 (11)	0.0203 (3)
H8	0.2279	0.0017	0.4909	0.024*
C9	0.20707 (4)	0.0509 (3)	0.61656 (11)	0.0178 (3)
C10	0.18289 (5)	0.1823 (3)	0.66407 (11)	0.0196 (3)
H10	0.1813	0.1492	0.7301	0.023*
C11	0.16114 (5)	0.3626 (3)	0.61267 (11)	0.0195 (3)
H11	0.1443	0.4568	0.6432	0.023*
O5	0.06125 (3)	0.4370 (2)	0.58801 (8)	0.0229 (3)
O6	0.01603 (3)	0.5377 (2)	0.66295 (8)	0.0261 (3)
O7	0.02485 (4)	0.7446 (2)	0.53506 (8)	0.0284 (3)
N4	0.03315 (4)	0.5777 (2)	0.59463 (9)	0.0187 (3)
H1	0.0541 (7)	−0.225 (5)	0.1953 (16)	0.050 (7)*
H2	0.0832 (6)	0.483 (4)	0.4735 (16)	0.035 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0163 (2)	0.0161 (2)	0.0213 (2)	−0.00180 (15)	0.00217 (14)	0.00219 (14)
O1	0.0227 (6)	0.0169 (6)	0.0324 (6)	−0.0003 (5)	−0.0007 (5)	−0.0045 (5)
O2	0.0219 (6)	0.0286 (7)	0.0270 (6)	−0.0035 (5)	0.0062 (5)	0.0110 (5)
O3	0.0306 (7)	0.0354 (7)	0.0299 (7)	0.0162 (6)	0.0023 (5)	−0.0040 (6)
O4	0.0333 (7)	0.0257 (7)	0.0257 (6)	0.0001 (6)	0.0029 (5)	0.0056 (5)
N1	0.0367 (10)	0.0211 (8)	0.0229 (7)	0.0070 (7)	−0.0106 (6)	−0.0066 (6)
N2	0.0157 (7)	0.0185 (7)	0.0168 (6)	−0.0016 (5)	0.0049 (5)	−0.0014 (5)
N3	0.0216 (8)	0.0185 (7)	0.0216 (7)	0.0016 (6)	−0.0012 (5)	−0.0035 (5)
C1	0.0171 (7)	0.0150 (7)	0.0142 (7)	0.0036 (6)	−0.0009 (5)	0.0020 (6)
C2	0.0167 (8)	0.0189 (8)	0.0192 (7)	−0.0012 (6)	0.0000 (6)	0.0033 (6)
C3	0.0232 (9)	0.0214 (9)	0.0296 (9)	−0.0017 (7)	−0.0062 (7)	0.0016 (7)
C4	0.0365 (11)	0.0289 (9)	0.0174 (8)	0.0103 (8)	0.0013 (7)	−0.0014 (7)
C5	0.0253 (9)	0.0247 (9)	0.0174 (7)	0.0052 (7)	0.0052 (6)	0.0030 (6)
C6	0.0149 (8)	0.0173 (8)	0.0185 (7)	−0.0030 (6)	0.0015 (5)	−0.0006 (6)
C7	0.0179 (8)	0.0243 (9)	0.0183 (7)	−0.0018 (7)	0.0055 (6)	0.0005 (6)
C8	0.0169 (8)	0.0237 (9)	0.0212 (8)	0.0016 (7)	0.0058 (6)	−0.0039 (6)
C9	0.0155 (8)	0.0177 (8)	0.0193 (7)	−0.0017 (6)	0.0004 (6)	−0.0023 (6)
C10	0.0210 (8)	0.0220 (8)	0.0158 (7)	−0.0015 (7)	0.0032 (6)	−0.0023 (6)
C11	0.0192 (8)	0.0212 (9)	0.0185 (7)	0.0004 (6)	0.0048 (6)	−0.0046 (6)
O5	0.0238 (6)	0.0257 (6)	0.0203 (6)	0.0055 (5)	0.0068 (4)	0.0010 (5)
O6	0.0281 (7)	0.0321 (7)	0.0211 (6)	0.0029 (5)	0.0125 (5)	0.0057 (5)
O7	0.0311 (7)	0.0268 (7)	0.0281 (6)	0.0048 (6)	0.0070 (5)	0.0132 (5)
N4	0.0208 (7)	0.0192 (7)	0.0165 (6)	−0.0017 (6)	0.0040 (5)	0.0008 (5)

S1—O1	1.4277 (12)	C4—C5	1.364 (2)
S1—O2	1.4286 (12)	C4—H4	0.9500
S1—N2	1.6358 (14)	C5—H5	0.9500
S1—C6	1.7687 (17)	C6—C7	1.389 (2)
O3—N3	1.2281 (18)	C6—C11	1.393 (2)
O4—N3	1.2243 (17)	C7—C8	1.385 (2)
N1—C4	1.333 (3)	C7—H7	0.9500
N1—C3	1.350 (2)	C8—C9	1.387 (2)
N1—H1	0.92 (2)	C8—H8	0.9500
N2—C1	1.392 (2)	C9—C10	1.383 (2)
N2—H2	0.79 (2)	C10—C11	1.377 (2)
N3—C9	1.472 (2)	C10—H10	0.9500
C1—C2	1.398 (2)	C11—H11	0.9500
C1—C5	1.400 (2)	O5—N4	1.2902 (17)
C2—C3	1.363 (2)	O6—N4	1.2427 (16)
C2—H2A	0.9500	O7—N4	1.2270 (17)
C3—H3	0.9500
O1—S1—O2	120.81 (7)	C5—C4—H4	119.6
O1—S1—N2	104.46 (7)	C4—C5—C1	119.05 (16)
O2—S1—N2	109.44 (8)	C4—C5—H5	120.5
O1—S1—C6	108.14 (7)	C1—C5—H5	120.5
O2—S1—C6	108.30 (8)	C7—C6—C11	121.62 (15)
N2—S1—C6	104.51 (7)	C7—C6—S1	120.35 (12)
C4—N1—C3	121.75 (15)	C11—C6—S1	117.96 (12)
C4—N1—H1	118.0 (14)	C8—C7—C6	118.90 (14)
C3—N1—H1	120.2 (14)	C8—C7—H7	120.5
C1—N2—S1	126.95 (11)	C6—C7—H7	120.5
C1—N2—H2	116.5 (16)	C7—C8—C9	118.47 (15)
S1—N2—H2	110.4 (16)	C7—C8—H8	120.8
O4—N3—O3	123.99 (14)	C9—C8—H8	120.8
O4—N3—C9	118.02 (14)	C10—C9—C8	123.25 (15)
O3—N3—C9	117.99 (13)	C10—C9—N3	118.54 (14)
N2—C1—C2	117.50 (13)	C8—C9—N3	118.19 (14)
N2—C1—C5	123.52 (15)	C11—C10—C9	117.92 (14)
C2—C1—C5	118.95 (14)	C11—C10—H10	121.0
C3—C2—C1	119.22 (15)	C9—C10—H10	121.0
C3—C2—H2A	120.4	C10—C11—C6	119.82 (15)
C1—C2—H2A	120.4	C10—C11—H11	120.1
N1—C3—C2	120.27 (17)	C6—C11—H11	120.1
N1—C3—H3	119.9	O7—N4—O6	123.22 (14)
C2—C3—H3	119.9	O7—N4—O5	119.33 (13)
N1—C4—C5	120.74 (16)	O6—N4—O5	117.45 (13)
N1—C4—H4	119.6
O1—S1—N2—C1	176.50 (13)	O2—S1—C6—C11	167.74 (12)
O2—S1—N2—C1	45.81 (15)	N2—S1—C6—C11	−75.67 (14)
C6—S1—N2—C1	−69.99 (14)	C11—C6—C7—C8	1.1 (2)
S1—N2—C1—C2	154.93 (12)	S1—C6—C7—C8	−175.84 (12)
S1—N2—C1—C5	−27.1 (2)	C6—C7—C8—C9	0.0 (2)
N2—C1—C2—C3	178.18 (14)	C7—C8—C9—C10	−1.0 (2)
C5—C1—C2—C3	0.1 (2)	C7—C8—C9—N3	177.55 (15)
C4—N1—C3—C2	0.9 (3)	O4—N3—C9—C10	15.6 (2)
C1—C2—C3—N1	−1.1 (2)	O3—N3—C9—C10	−165.41 (15)
C3—N1—C4—C5	0.4 (3)	O4—N3—C9—C8	−163.03 (15)
N1—C4—C5—C1	−1.4 (3)	O3—N3—C9—C8	16.0 (2)
N2—C1—C5—C4	−176.80 (15)	C8—C9—C10—C11	0.8 (2)
C2—C1—C5—C4	1.2 (2)	N3—C9—C10—C11	−177.68 (14)
O1—S1—C6—C7	−147.78 (13)	C9—C10—C11—C6	0.3 (2)
O2—S1—C6—C7	−15.24 (16)	C7—C6—C11—C10	−1.2 (2)
N2—S1—C6—C7	101.35 (14)	S1—C6—C11—C10	175.76 (13)
O1—S1—C6—C11	35.21 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5	0.79 (2)	1.92 (2)	2.7020 (19)	171 (2)
N1—H1···O5i	0.92 (2)	1.93 (2)	2.7764 (19)	151 (2)
N1—H1···O6i	0.92 (2)	2.18 (3)	2.979 (2)	144.6 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O5	0.79 (2)	1.92 (2)	2.7020 (19)	171 (2)
N1—H1⋯O5i	0.92 (2)	1.93 (2)	2.7764 (19)	151 (2)
N1—H1⋯O6i	0.92 (2)	2.18 (3)	2.979 (2)	144.6 (19)

Symmetry code: (i) .