2-(Benzene­sulfonamido)pyridinium perchlorate

Li, X.; Xie, D.; Xiao, Z.-H.; Li, C.-Z.

doi:10.1107/S1600536809019205

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1430

doi:10.1107/S1600536809019205

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2-(Benzenesulfonamido)pyridinium perchlorate

Xun Li,^a,^b ^* Dan Xie,^a Zhi-Hong Xiao ^b and Chang-Zhu Li ^b

^aSchool of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410004, People's Republic of China, and ^bHunan Provincial Research Center of Biodiesel Engineering and Technology, Changsha 410004, People's Republic of China
^*Correspondence e-mail: lixun0806@yahoo.com.cn

(Received 10 May 2009; accepted 20 May 2009; online 29 May 2009)

In the title compound, C₁₁H₁₁N₂O₂S⁺·ClO₄⁻, the dihedral angle between the benzene and pyridinium rings is 87.33 (10)°. An intramolecular N—H⋯O interaction, with an S=O-bonded O atom as receptor, occurs in the cation. In the crystal structure, ion pairs occur, being linked by strong N—H⋯O hydrogen bonds. The perchlorate anion plays a further role in the molecular packing by accepting several weak C—H⋯O interactions.

Related literature

For the synthesis, see: Li, Yang et al. (2008 ). For a related structure containing the same cation, see: Li & Li (2009 ). For related structures, see: Li et al. (2008a ,b ). For applications of pyridinium salts, see: Li et al. (2007 ); Li, Fan et al. (2008 ); Miyashita et al. (1977 ); Ganeshpure et al. (2007 ).

Experimental

Crystal data

C₁₁H₁₁N₂O₂S⁺·ClO₄⁻
M_r = 334.73
Triclinic, $[P \overline 1]$
a = 5.6594 (11) Å
b = 7.5996 (15) Å
c = 16.157 (3) Å
α = 83.21 (3)°
β = 83.70 (3)°
γ = 73.84 (3)°
V = 660.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 113 K
0.20 × 0.10 × 0.08 mm

Data collection

Rigaku Saturn CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.911, T_max = 0.963
5339 measured reflections
3051 independent reflections
2473 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.092
S = 1.07
3051 reflections
198 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.82 (2)	2.01 (2)	2.694 (2)	141 (2)
N2—H2A⋯O4	0.81 (2)	2.02 (2)	2.808 (2)	165 (2)
C1—H1⋯O3ⁱ	0.95	2.37	3.301 (3)	166
C3—H3⋯O5ⁱⁱ	0.95	2.44	3.303 (3)	151
C7—H7⋯O4ⁱⁱⁱ	0.95	2.53	3.417 (2)	156
C8—H8⋯O3ⁱⁱⁱ	0.95	2.58	3.251 (3)	128
Symmetry codes: (i) x+1, y+1, z; (ii) -x+1, -y, -z+1; (iii) x+1, y, z.

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: CrystalStructure (Rigaku/MSC, 2005).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019205/hb2972sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019205/hb2972Isup2.hkl

checkCIF report

Comment top

Organic pyridinium salts have been used as not only supramolecular guests (Li et al., 2007; Li, Fan, Fan et al., 2008), but also catalysts and/or media for esterification (Ganeshpure et al.2007; Miyashita et al. 1977). To seek a new pyridinium catalyst for biodiesel transformation, the title compound, (I), was synthesized and further determined by X-ray diffraction.

The title compound, (I), consists of a pyridinium cation and a perchlorate anion (Fig. 1). In the cation, the distance [1.383 (2) Å] between the pyridinum C atom and its connected amino N atom is slightly longer than the nitrate [1.378 (2) Å] (Li et al. 2009), also showing some conjugation of amino group with pyridinium ring. The benzene ring constructs an angle of 87.33 (10)° with the pyridinium ring, similar to the nitrate [87.59 (8)°]. The cation structure is stabilized by an intramolecular N—H···O hydrogen bond (Table 1), with S=O oxygen as H-bonding receptor, different from by C—H···O interaction in the nitrate.

Like the nitrate, in the crystal structure, a strong N—H···O hydrogen bond link the cation and anion (Table 1). The anion ClO₄ plays a great important role in the molecular packing via weak C—H···O interactions (Table 1).

Related literature top

For the synthesis, see: Li, Yang et al. (2008). For a related structure containing the same cation, see: Li & Li (2009). For related structures, see: Li et al. (2008a,b). For applications of pyridinium salts, see: Li et al. (2007); Li, Fan et al. (2008); Miyashita et al. (1977); Ganeshpure et al. (2007).

Experimental top

The title compound was prepared according to the reported literature (Li, Yang et al. 2008). Colourless needles of (I) were obtained by evaporation of a perchloric acid solution of the sulfonamide.

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: CrystalStructure (Rigaku/MSC, 2005).

Figures top

Fig. 1. View of the molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level and H atoms shown as small spheres of arbitrary radius. Dashed lines indicate hydrogen bonds.

2-(Benzenesulfonamido)pyridinium perchlorate top

Crystal data top

C₁₁H₁₁N₂O₂S⁺·ClO₄⁻	Z = 2
M_r = 334.73	F(000) = 344
Triclinic, P1	D_x = 1.683 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6594 (11) Å	Cell parameters from 2172 reflections
b = 7.5996 (15) Å	θ = 2.8–27.9°
c = 16.157 (3) Å	µ = 0.48 mm⁻¹
α = 83.21 (3)°	T = 113 K
β = 83.70 (3)°	Needle, colourless
γ = 73.84 (3)°	0.20 × 0.10 × 0.08 mm
V = 660.6 (2) Å³

Data collection top

Rigaku Saturn CCD diffractometer	3051 independent reflections
Radiation source: rotating anode	2473 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.024
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.8°
ω and ϕ scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −7→9
T_min = 0.911, T_max = 0.963	l = −19→21
5339 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0383P)² + 0.3333P] where P = (F_o² + 2F_c²)/3
3051 reflections	(Δ/σ)_max = 0.001
198 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₁H₁₁N₂O₂S⁺·ClO₄⁻	γ = 73.84 (3)°
M_r = 334.73	V = 660.6 (2) Å³
Triclinic, P1	Z = 2
a = 5.6594 (11) Å	Mo Kα radiation
b = 7.5996 (15) Å	µ = 0.48 mm⁻¹
c = 16.157 (3) Å	T = 113 K
α = 83.21 (3)°	0.20 × 0.10 × 0.08 mm
β = 83.70 (3)°

Data collection top

Rigaku Saturn CCD diffractometer	3051 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2473 reflections with I > 2σ(I)
T_min = 0.911, T_max = 0.963	R_int = 0.024
5339 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.32 e Å⁻³
3051 reflections	Δρ_min = −0.42 e Å⁻³
198 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
S1	0.22811 (8)	0.24398 (6)	0.16564 (3)	0.01285 (12)
O1	0.3752 (3)	0.36817 (19)	0.13565 (8)	0.0188 (3)
O2	−0.0260 (2)	0.2927 (2)	0.14890 (8)	0.0195 (3)
N1	0.5339 (3)	0.3703 (2)	0.28668 (10)	0.0146 (3)
N2	0.2351 (3)	0.2162 (2)	0.26820 (9)	0.0142 (3)
C1	0.6774 (3)	0.4261 (3)	0.33434 (12)	0.0178 (4)
H1	0.7775	0.5030	0.3096	0.021*
C2	0.6782 (4)	0.3717 (3)	0.41768 (12)	0.0202 (4)
H2	0.7815	0.4072	0.4513	0.024*
C3	0.5244 (4)	0.2628 (3)	0.45284 (12)	0.0214 (4)
H3	0.5208	0.2255	0.5111	0.026*
C4	0.3781 (4)	0.2091 (3)	0.40365 (11)	0.0167 (4)
H4	0.2729	0.1353	0.4276	0.020*
C5	0.3861 (3)	0.2644 (3)	0.31822 (11)	0.0133 (4)
C6	0.3713 (3)	0.0251 (2)	0.13242 (11)	0.0122 (3)
C7	0.6069 (3)	−0.0679 (3)	0.15558 (11)	0.0167 (4)
H7	0.6874	−0.0172	0.1915	0.020*
C8	0.7216 (4)	−0.2369 (3)	0.12480 (11)	0.0185 (4)
H8	0.8823	−0.3031	0.1397	0.022*
C9	0.6018 (4)	−0.3089 (3)	0.07244 (12)	0.0179 (4)
H9	0.6818	−0.4241	0.0514	0.021*
C10	0.3665 (4)	−0.2150 (3)	0.05020 (12)	0.0193 (4)
H10	0.2865	−0.2659	0.0142	0.023*
C11	0.2487 (3)	−0.0472 (3)	0.08060 (11)	0.0157 (4)
H11	0.0869	0.0175	0.0663	0.019*
H1A	0.536 (4)	0.398 (3)	0.2358 (15)	0.022 (6)*
H2A	0.152 (4)	0.150 (3)	0.2905 (14)	0.019 (6)*
Cl1	0.06395 (8)	−0.20083 (6)	0.34300 (3)	0.01538 (12)
O3	0.0680 (3)	−0.3209 (2)	0.28027 (10)	0.0267 (3)
O4	−0.0763 (2)	−0.01507 (19)	0.31513 (9)	0.0209 (3)
O5	0.3112 (3)	−0.1954 (2)	0.35352 (9)	0.0243 (3)
O6	−0.0508 (3)	−0.2619 (3)	0.42029 (10)	0.0415 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0155 (2)	0.0101 (2)	0.0123 (2)	−0.00192 (17)	−0.00278 (15)	−0.00055 (15)
O1	0.0296 (8)	0.0140 (7)	0.0144 (6)	−0.0102 (6)	−0.0003 (5)	0.0011 (5)
O2	0.0169 (7)	0.0168 (7)	0.0220 (7)	0.0020 (6)	−0.0067 (5)	−0.0018 (5)
N1	0.0152 (8)	0.0138 (8)	0.0152 (8)	−0.0041 (6)	−0.0009 (6)	−0.0024 (6)
N2	0.0156 (8)	0.0148 (8)	0.0139 (7)	−0.0075 (7)	0.0006 (6)	−0.0008 (6)
C1	0.0127 (9)	0.0145 (10)	0.0268 (10)	−0.0023 (7)	−0.0014 (7)	−0.0081 (8)
C2	0.0169 (9)	0.0203 (10)	0.0245 (10)	−0.0014 (8)	−0.0065 (7)	−0.0104 (8)
C3	0.0230 (10)	0.0221 (11)	0.0165 (9)	0.0006 (9)	−0.0036 (7)	−0.0052 (8)
C4	0.0190 (9)	0.0148 (10)	0.0152 (8)	−0.0032 (8)	0.0002 (7)	−0.0017 (7)
C5	0.0122 (8)	0.0097 (9)	0.0166 (8)	0.0003 (7)	−0.0012 (6)	−0.0029 (7)
C6	0.0149 (9)	0.0099 (9)	0.0119 (8)	−0.0035 (7)	−0.0007 (6)	−0.0004 (6)
C7	0.0171 (9)	0.0160 (10)	0.0173 (9)	−0.0032 (8)	−0.0056 (7)	−0.0020 (7)
C8	0.0179 (9)	0.0169 (10)	0.0170 (9)	0.0010 (8)	−0.0017 (7)	−0.0002 (7)
C9	0.0246 (10)	0.0108 (9)	0.0171 (9)	−0.0043 (8)	0.0017 (7)	−0.0009 (7)
C10	0.0241 (10)	0.0181 (10)	0.0187 (9)	−0.0088 (8)	−0.0029 (7)	−0.0049 (7)
C11	0.0152 (9)	0.0167 (10)	0.0159 (8)	−0.0051 (8)	−0.0032 (7)	−0.0005 (7)
Cl1	0.0175 (2)	0.0130 (2)	0.0159 (2)	−0.00511 (18)	−0.00268 (16)	0.00102 (16)
O3	0.0278 (8)	0.0179 (8)	0.0367 (8)	−0.0036 (7)	−0.0096 (6)	−0.0113 (6)
O4	0.0163 (7)	0.0104 (7)	0.0344 (8)	−0.0002 (6)	−0.0049 (6)	−0.0012 (6)
O5	0.0179 (7)	0.0235 (8)	0.0331 (8)	−0.0049 (6)	−0.0116 (6)	−0.0018 (6)
O6	0.0476 (11)	0.0515 (12)	0.0251 (8)	−0.0225 (10)	0.0047 (7)	0.0133 (8)

Geometric parameters (Å, º) top

S1—O2	1.4296 (14)	C4—H4	0.9500
S1—O1	1.4352 (15)	C6—C11	1.391 (3)
S1—N2	1.6488 (16)	C6—C7	1.393 (3)
S1—C6	1.7540 (19)	C7—C8	1.391 (3)
N1—C5	1.338 (2)	C7—H7	0.9500
N1—C1	1.356 (2)	C8—C9	1.384 (3)
N1—H1A	0.82 (2)	C8—H8	0.9500
N2—C5	1.383 (2)	C9—C10	1.388 (3)
N2—H2A	0.81 (2)	C9—H9	0.9500
C1—C2	1.361 (3)	C10—C11	1.384 (3)
C1—H1	0.9500	C10—H10	0.9500
C2—C3	1.395 (3)	C11—H11	0.9500
C2—H2	0.9500	Cl1—O6	1.4315 (16)
C3—C4	1.376 (3)	Cl1—O3	1.4358 (15)
C3—H3	0.9500	Cl1—O5	1.4403 (15)
C4—C5	1.394 (2)	Cl1—O4	1.4594 (15)

O2—S1—O1	119.45 (9)	N2—C5—C4	119.97 (17)
O2—S1—N2	106.71 (9)	C11—C6—C7	121.88 (18)
O1—S1—N2	106.24 (9)	C11—C6—S1	118.51 (14)
O2—S1—C6	108.52 (9)	C7—C6—S1	119.56 (14)
O1—S1—C6	110.07 (9)	C8—C7—C6	118.41 (18)
N2—S1—C6	104.81 (9)	C8—C7—H7	120.8
C5—N1—C1	122.75 (17)	C6—C7—H7	120.8
C5—N1—H1A	116.0 (17)	C9—C8—C7	120.05 (18)
C1—N1—H1A	121.3 (17)	C9—C8—H8	120.0
C5—N2—S1	129.79 (14)	C7—C8—H8	120.0
C5—N2—H2A	116.6 (16)	C8—C9—C10	120.91 (19)
S1—N2—H2A	112.8 (16)	C8—C9—H9	119.5
N1—C1—C2	119.98 (19)	C10—C9—H9	119.5
N1—C1—H1	120.0	C11—C10—C9	119.91 (18)
C2—C1—H1	120.0	C11—C10—H10	120.0
C1—C2—C3	118.80 (18)	C9—C10—H10	120.0
C1—C2—H2	120.6	C10—C11—C6	118.83 (18)
C3—C2—H2	120.6	C10—C11—H11	120.6
C4—C3—C2	120.39 (18)	C6—C11—H11	120.6
C4—C3—H3	119.8	O6—Cl1—O3	109.89 (11)
C2—C3—H3	119.8	O6—Cl1—O5	110.65 (10)
C3—C4—C5	119.16 (19)	O3—Cl1—O5	110.12 (10)
C3—C4—H4	120.4	O6—Cl1—O4	109.52 (11)
C5—C4—H4	120.4	O3—Cl1—O4	108.72 (9)
N1—C5—N2	121.08 (16)	O5—Cl1—O4	107.89 (9)
N1—C5—C4	118.89 (17)

O2—S1—N2—C5	−141.28 (17)	O1—S1—C6—C11	−118.07 (15)
O1—S1—N2—C5	−12.81 (19)	N2—S1—C6—C11	128.06 (15)
C6—S1—N2—C5	103.73 (18)	O2—S1—C6—C7	−168.22 (15)
C5—N1—C1—C2	1.1 (3)	O1—S1—C6—C7	59.37 (17)
N1—C1—C2—C3	−1.7 (3)	N2—S1—C6—C7	−54.50 (17)
C1—C2—C3—C4	1.1 (3)	C11—C6—C7—C8	0.7 (3)
C2—C3—C4—C5	0.2 (3)	S1—C6—C7—C8	−176.66 (14)
C1—N1—C5—N2	177.48 (17)	C6—C7—C8—C9	0.0 (3)
C1—N1—C5—C4	0.2 (3)	C7—C8—C9—C10	−0.3 (3)
S1—N2—C5—N1	9.9 (3)	C8—C9—C10—C11	−0.1 (3)
S1—N2—C5—C4	−172.85 (14)	C9—C10—C11—C6	0.8 (3)
C3—C4—C5—N1	−0.8 (3)	C7—C6—C11—C10	−1.1 (3)
C3—C4—C5—N2	−178.17 (17)	S1—C6—C11—C10	176.28 (14)
O2—S1—C6—C11	14.34 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.82 (2)	2.01 (2)	2.694 (2)	141 (2)
N2—H2A···O4	0.81 (2)	2.02 (2)	2.808 (2)	165 (2)
C1—H1···O3ⁱ	0.95	2.37	3.301 (3)	166
C3—H3···O5ⁱⁱ	0.95	2.44	3.303 (3)	151
C7—H7···O4ⁱⁱⁱ	0.95	2.53	3.417 (2)	156
C8—H8···O3ⁱⁱⁱ	0.95	2.58	3.251 (3)	128

Symmetry codes: (i) x+1, y+1, z; (ii) −x+1, −y, −z+1; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁N₂O₂S⁺·ClO₄⁻
M_r	334.73
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	5.6594 (11), 7.5996 (15), 16.157 (3)
α, β, γ (°)	83.21 (3), 83.70 (3), 73.84 (3)
V (Å³)	660.6 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.20 × 0.10 × 0.08

Data collection
Diffractometer	Rigaku Saturn CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.911, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	5339, 3051, 2473
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.092, 1.07
No. of reflections	3051
No. of parameters	198
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.42

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.82 (2)	2.01 (2)	2.694 (2)	141 (2)
N2—H2A···O4	0.81 (2)	2.02 (2)	2.808 (2)	165 (2)
C1—H1···O3ⁱ	0.95	2.37	3.301 (3)	166
C3—H3···O5ⁱⁱ	0.95	2.44	3.303 (3)	151
C7—H7···O4ⁱⁱⁱ	0.95	2.53	3.417 (2)	156
C8—H8···O3ⁱⁱⁱ	0.95	2.58	3.251 (3)	128

Symmetry codes: (i) x+1, y+1, z; (ii) −x+1, −y, −z+1; (iii) x+1, y, z.

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Volume 65| Part 6| June 2009| Page o1430

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