4-(4-Nitro-benzene-sulfonamido)pyri-dinium chloride.

In the title compound, C(11)H(10)N(3)O(4)S(+)·Cl(-), the benzene ring makes an angle of 89.2 (1)° with the pyridinium ring. The dihedral angle between the nitro group and the benzene ring is 15.7 (1)°. The crystal structure is stabilized by N-H⋯Cl hydrogen bonds.

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

C11H10N3O4S+·Cl−

M = 315.73

Monoclinic,

a = 37.942 (8) Å

b = 5.2446 (10) Å

c = 13.713 (3) Å

β = 107.77 (3)°

V = 2598.5 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.47 mm−1

T = 113 (2) K

0.12 × 0.10 × 0.08 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.932, T max = 0.963

9693 measured reflections

2865 independent reflections

2330 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.107

S = 1.06

2865 reflections

189 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.48 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/S1600536808032054/zl2146sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032054/zl2146Isup2.hkl

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

C11H10N3O4S+·Cl−	F(000) = 1296
Mr = 315.73	Dx = 1.614 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 37.942 (8) Å	Cell parameters from 3179 reflections
b = 5.2446 (10) Å	θ = 2.6–27.1°
c = 13.713 (3) Å	µ = 0.47 mm−1
β = 107.77 (3)°	T = 113 K
V = 2598.5 (9) Å3	Block, colourless
Z = 8	0.12 × 0.10 × 0.08 mm

Rigaku Saturn CCD area-detector diffractometer	2865 independent reflections
Radiation source: Rotating anode	2330 reflections with I > 2σ(I)
confocal	Rint = 0.043
Detector resolution: 7.21 pixels mm-1	θmax = 27.1°, θmin = 2.3°
ω and φ scans	h = −35→48
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −6→6
Tmin = 0.932, Tmax = 0.963	l = −17→13
9693 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0506P)2 + 1.967P] where P = (Fo2 + 2Fc2)/3
2865 reflections	(Δ/σ)max = 0.001
189 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

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	0.130148 (12)	0.37275 (10)	0.40268 (4)	0.02104 (16)
O1	0.12396 (4)	0.1690 (3)	0.32996 (12)	0.0268 (4)
O2	0.14305 (4)	0.3226 (3)	0.51052 (12)	0.0271 (4)
O3	0.21998 (4)	1.2270 (3)	0.21517 (12)	0.0320 (4)
O4	0.25562 (4)	1.2246 (3)	0.37259 (12)	0.0334 (4)
N1	0.05555 (5)	1.1001 (4)	0.52726 (16)	0.0297 (5)
N2	0.09049 (4)	0.5214 (4)	0.37499 (15)	0.0215 (4)
N3	0.22877 (5)	1.1462 (3)	0.30326 (14)	0.0246 (4)
C1	0.08046 (5)	0.7177 (4)	0.42979 (16)	0.0217 (4)
C2	0.10010 (6)	0.7864 (4)	0.52953 (17)	0.0253 (5)
H2	0.1227	0.7032	0.5645	0.030*
C3	0.08643 (6)	0.9760 (4)	0.57664 (18)	0.0284 (5)
H3	0.0992	1.0196	0.6456	0.034*
C4	0.03605 (6)	1.0410 (5)	0.43021 (19)	0.0323 (5)
H4	0.0141	1.1327	0.3966	0.039*
C5	0.04777 (5)	0.8496 (4)	0.38013 (18)	0.0277 (5)
H5	0.0338	0.8060	0.3120	0.033*
C6	0.16110 (5)	0.5922 (4)	0.37472 (16)	0.0190 (4)
C7	0.15830 (5)	0.6369 (4)	0.27247 (16)	0.0221 (5)
H7	0.1409	0.5446	0.2196	0.027*
C8	0.18104 (5)	0.8169 (4)	0.24842 (16)	0.0225 (4)
H8	0.1797	0.8499	0.1793	0.027*
C9	0.20570 (5)	0.9469 (4)	0.32797 (16)	0.0196 (4)
C10	0.20940 (5)	0.9012 (4)	0.43010 (16)	0.0229 (5)
H10	0.2272	0.9914	0.4827	0.028*
C11	0.18659 (5)	0.7207 (4)	0.45380 (16)	0.0223 (4)
H11	0.1884	0.6856	0.5231	0.027*
Cl1	0.038070 (13)	0.52540 (11)	0.65583 (4)	0.02598 (16)
H1	0.0477 (8)	1.233 (6)	0.561 (2)	0.058 (9)*
H2A	0.0771 (8)	0.504 (6)	0.310 (2)	0.059 (9)*

	U11	U22	U33	U12	U13	U23
S1	0.0197 (2)	0.0190 (3)	0.0238 (3)	0.00150 (18)	0.00570 (19)	0.0027 (2)
O1	0.0272 (7)	0.0204 (8)	0.0333 (9)	0.0011 (6)	0.0101 (6)	−0.0028 (7)
O2	0.0281 (7)	0.0289 (9)	0.0233 (9)	0.0018 (6)	0.0062 (6)	0.0100 (7)
O3	0.0388 (8)	0.0284 (9)	0.0310 (10)	−0.0013 (7)	0.0137 (7)	0.0059 (8)
O4	0.0313 (8)	0.0372 (10)	0.0321 (10)	−0.0125 (7)	0.0103 (7)	−0.0109 (8)
N1	0.0333 (10)	0.0246 (11)	0.0368 (12)	−0.0034 (8)	0.0190 (9)	−0.0056 (9)
N2	0.0189 (8)	0.0234 (10)	0.0207 (10)	0.0006 (7)	0.0038 (7)	−0.0008 (8)
N3	0.0261 (8)	0.0216 (10)	0.0287 (11)	−0.0001 (7)	0.0124 (7)	−0.0033 (8)
C1	0.0194 (9)	0.0231 (11)	0.0246 (11)	−0.0038 (8)	0.0097 (8)	0.0007 (9)
C2	0.0272 (10)	0.0249 (12)	0.0236 (12)	−0.0005 (8)	0.0074 (8)	0.0023 (10)
C3	0.0326 (11)	0.0301 (13)	0.0249 (12)	−0.0068 (9)	0.0126 (9)	−0.0016 (10)
C4	0.0261 (10)	0.0329 (14)	0.0392 (15)	0.0050 (9)	0.0117 (10)	−0.0031 (11)
C5	0.0209 (9)	0.0322 (13)	0.0281 (13)	0.0016 (8)	0.0046 (8)	−0.0034 (10)
C6	0.0185 (8)	0.0186 (11)	0.0195 (11)	0.0033 (7)	0.0055 (7)	0.0012 (8)
C7	0.0227 (9)	0.0222 (12)	0.0205 (11)	0.0000 (8)	0.0050 (8)	−0.0036 (9)
C8	0.0260 (9)	0.0239 (12)	0.0183 (11)	0.0013 (8)	0.0081 (8)	−0.0001 (9)
C9	0.0181 (8)	0.0205 (11)	0.0213 (11)	0.0009 (7)	0.0078 (7)	−0.0003 (9)
C10	0.0193 (9)	0.0277 (12)	0.0197 (11)	0.0008 (8)	0.0030 (8)	−0.0008 (9)
C11	0.0206 (9)	0.0275 (12)	0.0176 (11)	0.0011 (8)	0.0041 (7)	0.0013 (9)
Cl1	0.0256 (3)	0.0283 (3)	0.0228 (3)	0.00156 (19)	0.0056 (2)	−0.0007 (2)

S1—O1	1.4311 (16)	C2—H2	0.9500
S1—O2	1.4331 (16)	C3—H3	0.9500
S1—N2	1.6332 (17)	C4—C5	1.365 (3)
S1—C6	1.768 (2)	C4—H4	0.9500
O3—N3	1.226 (2)	C5—H5	0.9500
O4—N3	1.233 (2)	C6—C11	1.388 (3)
N1—C3	1.330 (3)	C6—C7	1.393 (3)
N1—C4	1.347 (3)	C7—C8	1.385 (3)
N1—H1	0.93 (3)	C7—H7	0.9500
N2—C1	1.394 (3)	C8—C9	1.381 (3)
N2—H2A	0.89 (3)	C8—H8	0.9500
N3—C9	1.468 (3)	C9—C10	1.385 (3)
C1—C2	1.391 (3)	C10—C11	1.387 (3)
C1—C5	1.402 (3)	C10—H10	0.9500
C2—C3	1.371 (3)	C11—H11	0.9500
O1—S1—O2	120.92 (10)	N1—C4—C5	120.1 (2)
O1—S1—N2	104.52 (10)	N1—C4—H4	120.0
O2—S1—N2	109.13 (10)	C5—C4—H4	120.0
O1—S1—C6	108.27 (10)	C4—C5—C1	119.6 (2)
O2—S1—C6	107.63 (10)	C4—C5—H5	120.2
N2—S1—C6	105.35 (9)	C1—C5—H5	120.2
C3—N1—C4	121.6 (2)	C11—C6—C7	121.73 (19)
C3—N1—H1	118.5 (18)	C11—C6—S1	119.82 (16)
C4—N1—H1	119.9 (18)	C7—C6—S1	118.42 (15)
C1—N2—S1	127.65 (15)	C8—C7—C6	119.50 (19)
C1—N2—H2A	117 (2)	C8—C7—H7	120.3
S1—N2—H2A	112.8 (19)	C6—C7—H7	120.3
O3—N3—O4	123.83 (19)	C9—C8—C7	118.0 (2)
O3—N3—C9	118.12 (18)	C9—C8—H8	121.0
O4—N3—C9	118.04 (18)	C7—C8—H8	121.0
C2—C1—N2	124.68 (19)	C8—C9—C10	123.26 (19)
C2—C1—C5	118.6 (2)	C8—C9—N3	118.51 (19)
N2—C1—C5	116.69 (19)	C10—C9—N3	118.22 (18)
C3—C2—C1	119.0 (2)	C9—C10—C11	118.50 (19)
C3—C2—H2	120.5	C9—C10—H10	120.8
C1—C2—H2	120.5	C11—C10—H10	120.8
N1—C3—C2	121.1 (2)	C10—C11—C6	118.97 (19)
N1—C3—H3	119.5	C10—C11—H11	120.5
C2—C3—H3	119.5	C6—C11—H11	120.5
O1—S1—N2—C1	172.50 (18)	O2—S1—C6—C7	168.84 (15)
O2—S1—N2—C1	41.8 (2)	N2—S1—C6—C7	−74.81 (18)
C6—S1—N2—C1	−73.5 (2)	C11—C6—C7—C8	−1.0 (3)
S1—N2—C1—C2	−14.1 (3)	S1—C6—C7—C8	176.94 (15)
S1—N2—C1—C5	167.25 (16)	C6—C7—C8—C9	−0.4 (3)
N2—C1—C2—C3	−177.14 (19)	C7—C8—C9—C10	1.8 (3)
C5—C1—C2—C3	1.5 (3)	C7—C8—C9—N3	−177.26 (17)
C4—N1—C3—C2	1.5 (3)	O3—N3—C9—C8	15.3 (3)
C1—C2—C3—N1	−2.4 (3)	O4—N3—C9—C8	−165.44 (18)
C3—N1—C4—C5	0.1 (3)	O3—N3—C9—C10	−163.75 (18)
N1—C4—C5—C1	−1.0 (4)	O4—N3—C9—C10	15.5 (3)
C2—C1—C5—C4	0.1 (3)	C8—C9—C10—C11	−1.7 (3)
N2—C1—C5—C4	178.9 (2)	N3—C9—C10—C11	177.29 (17)
O1—S1—C6—C11	−145.42 (16)	C9—C10—C11—C6	0.3 (3)
O2—S1—C6—C11	−13.15 (19)	C7—C6—C11—C10	1.1 (3)
N2—S1—C6—C11	103.20 (18)	S1—C6—C11—C10	−176.88 (15)
O1—S1—C6—C7	36.57 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1i	0.93 (3)	2.12 (3)	3.039 (2)	171 (3)
N2—H2A···Cl1ii	0.89 (3)	2.18 (3)	3.066 (2)	173 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1i	0.93 (3)	2.12 (3)	3.039 (2)	171 (3)
N2—H2A⋯Cl1ii	0.89 (3)	2.18 (3)	3.066 (2)	173 (3)

Symmetry codes: (i) ; (ii) .