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

In the title compound, C(11)H(10)N(3)O(4)S(+)·Br(-), the benzene ring makes an angle of 88.4 (2)° with the pyridinium ring. The dihedral angle between the nitro group and the benzene ring is 16.5 (2)°. The ions in the crystal structure are linked by a combination of inter-molecular N-H⋯Br and non-conventional C-H⋯Br and C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For zwitterionic forms of N-aryl­benzene­sulfonamides, see: Li et al. (2007 ▶); Yu & Li (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶). For non-conventional hydrogen bonds, see: Desiraju & Steiner (2001 ▶). For the use of pyridinium derivatives in the construction of supra­molecular architectures, see: Damiano et al. (2007 ▶).

Experimental

Crystal data

C11H10N3O4S+·Br−

M = 360.19

Monoclinic,

a = 38.242 (8) Å

b = 5.2852 (11) Å

c = 13.941 (3) Å

β = 108.18 (3)°

V = 2677.0 (11) Å3

Z = 8

Mo Kα radiation

μ = 3.24 mm−1

T = 113 (2) K

0.10 × 0.04 × 0.02 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.710, T max = 0.938

10460 measured reflections

3174 independent reflections

2635 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.076

S = 1.05

3174 reflections

189 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.68 e Å−3

Δρmin = −0.47 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/S1600536808035265/si2122sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035265/si2122Isup2.hkl

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

C11H10N3O4S+·Br–	F000 = 1440
Mr = 360.19	Dx = 1.787 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3479 reflections
a = 38.242 (8) Å	θ = 2.2–27.9º
b = 5.2852 (11) Å	µ = 3.24 mm−1
c = 13.941 (3) Å	T = 113 (2) K
β = 108.18 (3)º	Needle, colorless
V = 2677.0 (11) Å3	0.10 × 0.04 × 0.02 mm
Z = 8

Rigaku Saturn CCD area-detector diffractometer	3174 independent reflections
Radiation source: rotating anode	2635 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.050
Detector resolution: 7.31 pixels mm-1	θmax = 27.9º
T = 113(2) K	θmin = 2.2º
ω and φ scans	h = −45→50
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)	k = −6→4
Tmin = 0.710, Tmax = 0.938	l = −18→18
10460 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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.0332P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3174 reflections	Δρmax = 0.68 e Å−3
189 parameters	Δρmin = −0.47 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
Br1	0.038458 (6)	−0.03831 (5)	0.156635 (19)	0.02228 (9)
S1	0.134013 (15)	−0.12886 (11)	0.40908 (5)	0.01823 (14)
O1	0.14776 (4)	−0.1752 (3)	0.51529 (13)	0.0248 (4)
O2	0.12760 (4)	−0.3323 (3)	0.33820 (13)	0.0240 (4)
O3	0.25567 (5)	0.7285 (4)	0.36991 (13)	0.0304 (4)
O4	0.21939 (5)	0.7239 (3)	0.21551 (13)	0.0277 (4)
N1	0.05972 (6)	0.5912 (4)	0.53090 (18)	0.0279 (5)
N2	0.09433 (5)	0.0162 (4)	0.38299 (17)	0.0191 (4)
N3	0.22900 (5)	0.6463 (4)	0.30319 (16)	0.0207 (4)
C1	0.09132 (7)	0.4746 (5)	0.5789 (2)	0.0271 (6)
H1	0.1046	0.5230	0.6460	0.033*
C2	0.10479 (6)	0.2877 (5)	0.53330 (18)	0.0227 (5)
H2	0.1277	0.2101	0.5672	0.027*
C3	0.08437 (6)	0.2113 (5)	0.43571 (18)	0.0196 (5)
C4	0.05109 (6)	0.3348 (5)	0.38843 (19)	0.0261 (6)
H4	0.0365	0.2863	0.3224	0.031*
C5	0.03964 (7)	0.5254 (5)	0.4376 (2)	0.0304 (6)
H5	0.0173	0.6115	0.4053	0.036*
C6	0.16392 (6)	0.0923 (4)	0.37923 (18)	0.0165 (5)
C7	0.16066 (6)	0.1306 (5)	0.27787 (18)	0.0192 (5)
H7	0.1436	0.0342	0.2268	0.023*
C8	0.18247 (6)	0.3099 (5)	0.25237 (17)	0.0186 (5)
H8	0.1808	0.3389	0.1838	0.022*
C9	0.20687 (6)	0.4465 (4)	0.32927 (18)	0.0164 (5)
C10	0.21101 (6)	0.4056 (5)	0.43050 (18)	0.0188 (5)
H10	0.2285	0.4995	0.4815	0.023*
C11	0.18912 (6)	0.2252 (5)	0.45572 (17)	0.0193 (5)
H11	0.1914	0.1931	0.5244	0.023*
H1A	0.0529 (8)	0.723 (6)	0.561 (2)	0.040 (8)*
H2A	0.0799 (8)	−0.010 (5)	0.324 (2)	0.018 (7)*

	U11	U22	U33	U12	U13	U23
Br1	0.02226 (14)	0.02479 (15)	0.01857 (15)	−0.00186 (10)	0.00461 (11)	−0.00007 (10)
S1	0.0162 (3)	0.0167 (3)	0.0210 (3)	0.0022 (2)	0.0046 (2)	0.0039 (2)
O1	0.0228 (8)	0.0270 (10)	0.0216 (10)	0.0012 (8)	0.0025 (7)	0.0111 (8)
O2	0.0219 (8)	0.0179 (9)	0.0323 (10)	0.0006 (7)	0.0085 (8)	−0.0030 (8)
O3	0.0290 (9)	0.0333 (11)	0.0296 (11)	−0.0136 (8)	0.0099 (8)	−0.0083 (9)
O4	0.0351 (10)	0.0260 (10)	0.0230 (10)	−0.0022 (8)	0.0105 (8)	0.0055 (8)
N1	0.0323 (12)	0.0243 (12)	0.0317 (14)	−0.0043 (10)	0.0170 (11)	−0.0065 (10)
N2	0.0139 (10)	0.0224 (11)	0.0182 (12)	0.0011 (8)	0.0010 (9)	−0.0021 (9)
N3	0.0230 (10)	0.0178 (10)	0.0248 (12)	0.0004 (9)	0.0124 (9)	−0.0026 (9)
C1	0.0280 (14)	0.0316 (15)	0.0234 (15)	−0.0087 (11)	0.0104 (12)	−0.0043 (12)
C2	0.0209 (12)	0.0261 (13)	0.0209 (13)	−0.0024 (10)	0.0063 (11)	0.0011 (11)
C3	0.0186 (11)	0.0182 (12)	0.0250 (13)	−0.0050 (10)	0.0109 (10)	−0.0001 (10)
C4	0.0203 (12)	0.0310 (15)	0.0256 (15)	0.0033 (11)	0.0052 (11)	−0.0009 (12)
C5	0.0246 (13)	0.0292 (15)	0.0398 (17)	0.0059 (11)	0.0136 (13)	0.0012 (13)
C6	0.0137 (10)	0.0182 (12)	0.0163 (12)	0.0017 (9)	0.0029 (9)	0.0013 (9)
C7	0.0204 (11)	0.0185 (12)	0.0162 (13)	0.0008 (10)	0.0022 (10)	−0.0038 (10)
C8	0.0226 (11)	0.0208 (12)	0.0129 (11)	0.0003 (10)	0.0063 (10)	−0.0005 (10)
C9	0.0172 (11)	0.0146 (11)	0.0194 (13)	0.0029 (9)	0.0087 (10)	0.0011 (10)
C10	0.0160 (11)	0.0232 (12)	0.0149 (12)	0.0011 (9)	0.0015 (10)	−0.0018 (10)
C11	0.0175 (11)	0.0246 (13)	0.0146 (12)	0.0042 (10)	0.0032 (9)	0.0037 (10)

S1—O2	1.4288 (18)	C2—H2	0.9500
S1—O1	1.4292 (18)	C3—C4	1.399 (3)
S1—N2	1.637 (2)	C4—C5	1.366 (4)
S1—C6	1.773 (2)	C4—H4	0.9500
O3—N3	1.226 (3)	C5—H5	0.9500
O4—N3	1.232 (3)	C6—C11	1.385 (3)
N1—C5	1.333 (4)	C6—C7	1.394 (3)
N1—C1	1.335 (4)	C7—C8	1.380 (3)
N1—H1A	0.89 (3)	C7—H7	0.9500
N2—C3	1.387 (3)	C8—C9	1.385 (3)
N2—H2A	0.84 (3)	C8—H8	0.9500
N3—C9	1.468 (3)	C9—C10	1.387 (3)
C1—C2	1.359 (3)	C10—C11	1.385 (3)
C1—H1	0.9500	C10—H10	0.9500
C2—C3	1.400 (3)	C11—H11	0.9500
O2—S1—O1	121.05 (11)	C5—C4—C3	119.6 (3)
O2—S1—N2	104.58 (11)	C5—C4—H4	120.2
O1—S1—N2	109.04 (11)	C3—C4—H4	120.2
O2—S1—C6	108.52 (10)	N1—C5—C4	120.3 (2)
O1—S1—C6	107.48 (11)	N1—C5—H5	119.8
N2—S1—C6	105.09 (11)	C4—C5—H5	119.8
C5—N1—C1	121.6 (2)	C11—C6—C7	121.8 (2)
C5—N1—H1A	120.0 (19)	C11—C6—S1	119.90 (17)
C1—N1—H1A	118.3 (19)	C7—C6—S1	118.27 (18)
C3—N2—S1	128.28 (19)	C8—C7—C6	119.4 (2)
C3—N2—H2A	115.5 (17)	C8—C7—H7	120.3
S1—N2—H2A	114.9 (18)	C6—C7—H7	120.3
O3—N3—O4	123.7 (2)	C7—C8—C9	118.3 (2)
O3—N3—C9	118.3 (2)	C7—C8—H8	120.9
O4—N3—C9	117.9 (2)	C9—C8—H8	120.9
N1—C1—C2	121.1 (3)	C8—C9—C10	122.8 (2)
N1—C1—H1	119.4	C8—C9—N3	119.0 (2)
C2—C1—H1	119.4	C10—C9—N3	118.2 (2)
C1—C2—C3	119.1 (2)	C11—C10—C9	118.7 (2)
C1—C2—H2	120.5	C11—C10—H10	120.7
C3—C2—H2	120.5	C9—C10—H10	120.7
N2—C3—C4	117.2 (2)	C10—C11—C6	119.0 (2)
N2—C3—C2	124.6 (2)	C10—C11—H11	120.5
C4—C3—C2	118.2 (2)	C6—C11—H11	120.5
O2—S1—N2—C3	172.9 (2)	O1—S1—C6—C7	167.55 (17)
O1—S1—N2—C3	42.1 (2)	N2—S1—C6—C7	−76.4 (2)
C6—S1—N2—C3	−72.9 (2)	C11—C6—C7—C8	−1.6 (3)
C5—N1—C1—C2	1.7 (4)	S1—C6—C7—C8	177.10 (17)
N1—C1—C2—C3	−2.3 (4)	C6—C7—C8—C9	−0.2 (3)
S1—N2—C3—C4	168.56 (19)	C7—C8—C9—C10	1.9 (3)
S1—N2—C3—C2	−13.2 (3)	C7—C8—C9—N3	−177.11 (19)
C1—C2—C3—N2	−177.1 (2)	O3—N3—C9—C8	−164.7 (2)
C1—C2—C3—C4	1.1 (3)	O4—N3—C9—C8	16.1 (3)
N2—C3—C4—C5	178.9 (2)	O3—N3—C9—C10	16.2 (3)
C2—C3—C4—C5	0.5 (4)	O4—N3—C9—C10	−162.90 (19)
C1—N1—C5—C4	0.0 (4)	C8—C9—C10—C11	−1.8 (3)
C3—C4—C5—N1	−1.1 (4)	N3—C9—C10—C11	177.23 (19)
O2—S1—C6—C11	−146.30 (18)	C9—C10—C11—C6	0.0 (3)
O1—S1—C6—C11	−13.8 (2)	C7—C6—C11—C10	1.7 (3)
N2—S1—C6—C11	102.3 (2)	S1—C6—C11—C10	−176.96 (17)
O2—S1—C6—C7	35.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br1i	0.89 (3)	2.30 (3)	3.195 (2)	173 (3)
N2—H2A···Br1	0.84 (3)	2.38 (3)	3.225 (3)	174 (2)
C10—H10···O3ii	0.95	2.44	3.301 (3)	151
C5—H5···Br1iii	0.95	2.75	3.676 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Br1i	0.89 (3)	2.30 (3)	3.195 (2)	173 (3)
N2—H2A⋯Br1	0.84 (3)	2.38 (3)	3.225 (3)	174 (2)
C10—H10⋯O3ii	0.95	2.44	3.301 (3)	151
C5—H5⋯Br1iii	0.95	2.75	3.676 (3)	165

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