4-(4-Nitro­benzene­sulfonamido)pyridinium bromide

Zhao, L.; Yu, Q.-F.; Wu, Q.

doi:10.1107/S1600536808035265

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2308

doi:10.1107/S1600536808035265

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4-(4-Nitrobenzenesulfonamido)pyridinium bromide

Liang Zhao,^a ^* Qi-Fei Yu ^b and Qiong Wu ^c

^aSchool of Food Science, Henan Institute of Science and Technology, Xinxiang 453003, People's Republic of China, ^bDepartment of Food and Biological Engineering, Zhangzhou Institute of Technology, Zhangzhou 363000, People's Republic of China, and ^cJilin Key Laboratory for the Biotechnology of Agricultural Products Processing, Changchun University, Changchun 130022, People's Republic of China
^*Correspondence e-mail: l_zhaohn@yahoo.cn

(Received 19 October 2008; accepted 29 October 2008; online 13 November 2008)

In the title compound, C₁₁H₁₀N₃O₄S⁺·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 intermolecular 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_r = 360.19
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.033
wR(F²) = 0.076
S = 1.05
3174 reflections
189 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.47 e Å⁻³

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) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iii) $[-x, y+1, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035265/si2122sup1.cif

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

checkCIF report

Comment top

Organic pyridinium salts have been widely used in the construction of supramolecular architectures (Damiano et al., 2007). As part of our ongoing studies of supramolecular chemistry involving the pyridinium rings (Li et al., 2007), an X-ray structure analysis of the title compound has been performed. In the cations of the title compound the short C—N distance [N2—C3 = 1.387 (3) Å] has a value between those of a typical C=N double and C—N single bond (1.34–1.38 Å and 1.47–1.50 Å, respectively; Allen et al., 1987). This might be indicative of a slight conjugation of the sulphonamide π electrons N with those of the pyridinium ring. 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 163.5 (2) °. The S atom has a tetrahedral geometry and the Br anion link the cationic molecule into chains along the c axis. The ions in the crystal structure are linked by a combination of intermolecular N—H···Br and non-conventional C—H···Br and C—H···O hydrogen bonds (Table 1) to form a three-dimensional network (Desiraju & Steiner, 2001).

Related literature top

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 top

A solution of 4-nitrobenzenesulfonyl chloride (2.2 g, 10 mmol) in CH₂Cl₂ (10 ml) was added dropwise to a suspension of 4-aminopyridine (0.9 g, 10 mmol) in CH₂Cl₂ (10 ml) at room temperature with stirring. The reaction mixture was stirred overnight. The yellow solid obtained was washed with warm water to obtain the title compound in a yield of 60.6%. A colorless single-crystal suitable for X-ray analysis was obtained by slow evaporation of an hydrobromic acid (5%) solution at room temperature over a period of a week. Analysis calculated for C₁₁H₁₀N₃O₄SBr: C 36.68, H 2.80, N 11.67%; found: C 36.70, H 2.52, N 11.98%.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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 (Sheldrick, 2008).

Figures top

Fig. 1. View of one molecule of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level (arbitrary spheres for the H atoms).

4-(4-Nitrobenzenesulfonamido)pyridinium bromide top

Crystal data top

C₁₁H₁₀N₃O₄S⁺·Br⁻	F(000) = 1440
M_r = 360.19	D_x = 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 = 2.2–27.9°
b = 5.2852 (11) Å	µ = 3.24 mm⁻¹
c = 13.941 (3) Å	T = 113 K
β = 108.18 (3)°	Needle, colorless
V = 2677.0 (11) Å³	0.10 × 0.04 × 0.02 mm
Z = 8

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3174 independent reflections
Radiation source: rotating anode	2635 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.050
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.2°
ω and ϕ scans	h = −45→50
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −6→4
T_min = 0.710, T_max = 0.938	l = −18→18
10460 measured reflections

Refinement top

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0332P)²] where P = (F_o² + 2F_c²)/3
3174 reflections	(Δ/σ)_max = 0.001
189 parameters	Δρ_max = 0.68 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₁H₁₀N₃O₄S⁺·Br⁻	V = 2677.0 (11) Å³
M_r = 360.19	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 38.242 (8) Å	µ = 3.24 mm⁻¹
b = 5.2852 (11) Å	T = 113 K
c = 13.941 (3) Å	0.10 × 0.04 × 0.02 mm
β = 108.18 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3174 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2635 reflections with I > 2σ(I)
T_min = 0.710, T_max = 0.938	R_int = 0.050
10460 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.68 e Å⁻³
3174 reflections	Δρ_min = −0.47 e Å⁻³
189 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+1, z+1/2; (ii) −x+1/2, −y+3/2, −z+1; (iii) −x, y+1, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀N₃O₄S⁺·Br⁻
M_r	360.19
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	113
a, b, c (Å)	38.242 (8), 5.2852 (11), 13.941 (3)
β (°)	108.18 (3)
V (Å³)	2677.0 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.24
Crystal size (mm)	0.10 × 0.04 × 0.02

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.710, 0.938
No. of measured, independent and observed [I > 2σ(I)] reflections	10460, 3174, 2635
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.076, 1.05
No. of reflections	3174
No. of parameters	189
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.47

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x, −y+1, z+1/2; (ii) −x+1/2, −y+3/2, −z+1; (iii) −x, y+1, −z+1/2.

References

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Volume 64| Part 12| December 2008| Page o2308

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