4-(2-Nitro­benzene­sulfonamido)pyridinium nitrate

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

doi:10.1107/S1600536808035654

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2281

doi:10.1107/S1600536808035654

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4-(2-Nitrobenzenesulfonamido)pyridinium nitrate

Liang Zhao ^a ^* and Qi-Fei Yu ^b

^aSchool of Food Science, Henan Institute of Science and Technology, Xinxiang 453003, People's Republic of China, and ^bDepartment of Food and Biological Engineering, Zhangzhou Institute of Technology, Henan University of Technology, Zhangzhou 363000, People's Republic of China
^*Correspondence e-mail: l_zhaohn@yahoo.cn

(Received 23 October 2008; accepted 30 October 2008; online 8 November 2008)

There are two molecules in the asymmetric unit of the title compound, C₁₁H₁₀N₃O₄S⁺·NO₃⁻. All bond distances have normal values. The C—N bond distances in the sulfonamide group [1.389 (3) and 1.382 (3) Å] may indicate slight conjugation of the sulfonamide N-atom 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 ). Damiano et al. (2007 ) describe the use of pyridinium derivatives for the construction of supramolecular architectures. For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₁₀N₃O₄S⁺·NO₃⁻
M_r = 342.30
Orthorhombic, P n a 2₁
a = 14.716 (3) Å
b = 8.6671 (17) Å
c = 21.941 (4) Å
V = 2798.5 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 113 (2) K
0.20 × 0.16 × 0.02 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.943, T_max = 0.998
20607 measured reflections
5734 independent reflections
5237 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.098
S = 1.04
5734 reflections
432 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.33 e Å⁻³
Absolute structure: Flack (1983 ), 2570 Friedel pairs
Flack parameter: 0.14 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O11ⁱ	1.06 (4)	1.68 (4)	2.745 (3)	179 (3)
N1—H1A⋯O9ⁱ	1.06 (4)	2.65 (3)	3.361 (3)	124 (2)
N4—H4A⋯O13ⁱⁱ	0.90 (3)	1.85 (3)	2.737 (3)	171 (2)
N4—H4A⋯O12ⁱⁱ	0.90 (3)	2.68 (3)	3.273 (3)	124 (2)
N5—H5A⋯O13ⁱⁱⁱ	0.94 (3)	1.87 (3)	2.751 (3)	155 (2)
N2—H2A⋯O11^iv	0.97 (4)	1.78 (4)	2.725 (3)	166 (4)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (ii) $[-x+2, -y, z-{\script{1\over 2}}]$ ; (iii) $[-x+2, -y+1, z-{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035654/rk2115sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808035654/rk2115Isup2.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), the structure of the title compound was determined by X–ray diffraction. In the cations of the title compound the short C–N distance [N2–C1 = 1.389 (3)Å and N5–C12 = 1.382 (3)Å] has a value between those of a typical C═N double and C—N single bond (1.47–1.50Å and 1.34–1.38Å, respectively; Allen et al., 1987). This might be indicative of a slight conjugation of the N sulfonamide π–electrons with those of the pyridinium ring. In the two symmetry–independent molecules (Fig. 1), the dihedral angles between the benzene ring and the pyridinium ring are 85.1 (1)° and 86.2 (1)° respectively. The dihedral angles between the nitro–group and the benzene ring are 41.2 (1)° and 40.5 (2)° respectively.

Related literature top

For zwitterionic forms of N–arylbenzenesulfonamides, see: Li et al. (2007); Yu & Li (2007). Damiano et al. (2007) describe the use of pyridinium derivatives for the construction of supramolecular architectures. For bond-length data, see: Allen et al. (1987).

Experimental top

A solution of 2–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 52.9%. A colourless single crystals, suitable for X–ray analysis were obtained by slow evaporation of an nitric acid (10%) solution at room temperature over a period of a week.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalStructure (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. The molecular structure of the title compound, showing the two symmetry-independent molecules with the atom numbering scheme. Displacement ellipsoids are drawn at the 35% probability level. H atoms are presented as a small spheres of arbitrary radius.

4-(2-Nitrobenzenesulfonamido)pyridinium nitrate top

Crystal data top

C₁₁H₁₀N₃O₄S⁺·NO₃⁻	F(000) = 1408
M_r = 342.30	D_x = 1.625 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 8078 reflections
a = 14.716 (3) Å	θ = 3.1–27.1°
b = 8.6671 (17) Å	µ = 0.28 mm⁻¹
c = 21.941 (4) Å	T = 113 K
V = 2798.5 (9) Å³	Block, colourless
Z = 8	0.20 × 0.16 × 0.02 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	5734 independent reflections
Radiation source: Rotating anode	5237 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.046
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.1°, θ_min = 3.3°
ω scans	h = −18→18
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −11→9
T_min = 0.943, T_max = 0.998	l = −20→28
20607 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: Full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.040	w = 1/[σ²(F_o²) + (0.0538P)² + 0.0901P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.098	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 0.42 e Å⁻³
5734 reflections	Δρ_min = −0.33 e Å⁻³
432 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0054 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2570 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.14 (6)

Crystal data top

C₁₁H₁₀N₃O₄S⁺·NO₃⁻	V = 2798.5 (9) Å³
M_r = 342.30	Z = 8
Orthorhombic, Pna2₁	Mo Kα radiation
a = 14.716 (3) Å	µ = 0.28 mm⁻¹
b = 8.6671 (17) Å	T = 113 K
c = 21.941 (4) Å	0.20 × 0.16 × 0.02 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	5734 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	5237 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.998	R_int = 0.046
20607 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.098	Δρ_max = 0.42 e Å⁻³
S = 1.04	Δρ_min = −0.33 e Å⁻³
5734 reflections	Absolute structure: Flack (1983), 2570 Friedel pairs
432 parameters	Absolute structure parameter: 0.14 (6)
1 restraint

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.55489 (4)	0.54735 (7)	0.70897 (3)	0.01874 (14)
S2	0.74559 (4)	0.43842 (7)	0.42871 (3)	0.02018 (14)
O1	0.63055 (12)	0.5867 (2)	0.74667 (8)	0.0233 (4)
O2	0.53170 (13)	0.3890 (2)	0.69999 (8)	0.0248 (4)
O3	0.38958 (15)	0.5302 (3)	0.62281 (9)	0.0384 (5)
O4	0.4342 (2)	0.4321 (4)	0.53747 (12)	0.0689 (10)
O5	0.66949 (13)	0.3918 (2)	0.39273 (8)	0.0256 (4)
O6	0.76670 (13)	0.5983 (2)	0.43544 (9)	0.0270 (4)
O7	0.91479 (15)	0.4690 (3)	0.51112 (10)	0.0437 (6)
O8	0.8745 (2)	0.5660 (4)	0.59706 (13)	0.0769 (11)
N1	0.40728 (15)	1.0904 (3)	0.75443 (9)	0.0202 (4)
N2	0.46295 (15)	0.6264 (2)	0.73697 (9)	0.0185 (4)
N3	0.44496 (18)	0.5160 (3)	0.58163 (11)	0.0330 (6)
N4	0.89765 (15)	−0.1009 (3)	0.37907 (9)	0.0186 (4)
N5	0.83710 (16)	0.3598 (3)	0.40056 (9)	0.0200 (5)
N6	0.86294 (19)	0.4797 (3)	0.55345 (11)	0.0361 (6)
C1	0.44743 (16)	0.7834 (3)	0.74440 (10)	0.0160 (5)
C2	0.35733 (17)	0.8310 (3)	0.75337 (10)	0.0173 (5)
H2	0.3096	0.7576	0.7560	0.021*
C3	0.33974 (17)	0.9853 (3)	0.75823 (11)	0.0191 (5)
H3	0.2790	1.0192	0.7644	0.023*
C4	0.49413 (18)	1.0467 (3)	0.74780 (11)	0.0199 (5)
H4	0.5406	1.1227	0.7465	0.024*
C5	0.51674 (19)	0.8933 (3)	0.74283 (11)	0.0205 (5)
H5	0.5784	0.8626	0.7384	0.025*
C6	0.57669 (18)	0.6366 (3)	0.63708 (11)	0.0206 (5)
C7	0.65379 (17)	0.7288 (3)	0.63400 (11)	0.0220 (5)
H7	0.6886	0.7462	0.6698	0.026*
C8	0.6808 (2)	0.7962 (3)	0.57937 (12)	0.0255 (6)
H8	0.7331	0.8602	0.5781	0.031*
C9	0.6311 (2)	0.7697 (3)	0.52707 (12)	0.0279 (6)
H9	0.6491	0.8159	0.4897	0.033*
C10	0.5556 (2)	0.6764 (4)	0.52898 (12)	0.0307 (7)
H10	0.5221	0.6572	0.4928	0.037*
C11	0.52818 (19)	0.6104 (3)	0.58340 (12)	0.0226 (5)
C12	0.85468 (17)	0.2042 (3)	0.39336 (10)	0.0180 (5)
C13	0.94527 (17)	0.1584 (3)	0.38431 (10)	0.0181 (5)
H13	0.9925	0.2331	0.3832	0.022*
C14	0.96478 (19)	0.0056 (3)	0.37715 (11)	0.0206 (5)
H14	1.0258	−0.0262	0.3708	0.025*
C15	0.80967 (19)	−0.0599 (3)	0.38700 (11)	0.0214 (5)
H15	0.7638	−0.1370	0.3875	0.026*
C16	0.78660 (18)	0.0911 (3)	0.39421 (11)	0.0190 (5)
H16	0.7248	0.1196	0.3998	0.023*
C17	0.72784 (18)	0.3544 (3)	0.50237 (11)	0.0207 (5)
C18	0.65166 (18)	0.2619 (3)	0.50870 (11)	0.0247 (6)
H18	0.6141	0.2427	0.4743	0.030*
C19	0.6294 (2)	0.1970 (3)	0.56452 (12)	0.0283 (6)
H19	0.5777	0.1320	0.5678	0.034*
C20	0.6817 (2)	0.2263 (4)	0.61506 (13)	0.0336 (7)
H20	0.6664	0.1814	0.6532	0.040*
C21	0.7570 (2)	0.3217 (4)	0.61016 (13)	0.0337 (7)
H21	0.7926	0.3443	0.6452	0.040*
C22	0.7801 (2)	0.3839 (3)	0.55443 (12)	0.0275 (6)
O9	0.71160 (13)	0.2133 (2)	0.76947 (9)	0.0310 (5)
O10	0.72427 (15)	−0.0296 (2)	0.74762 (11)	0.0348 (5)
O11	0.84491 (13)	0.1111 (2)	0.75566 (10)	0.0280 (4)
N7	0.75865 (15)	0.0975 (2)	0.75795 (10)	0.0198 (5)
O12	0.91094 (12)	0.2926 (2)	0.88498 (8)	0.0256 (4)
O13	1.04400 (13)	0.4007 (2)	0.88032 (9)	0.0257 (4)
O14	0.92515 (15)	0.5367 (2)	0.90341 (10)	0.0318 (5)
N8	0.95891 (15)	0.4105 (2)	0.89013 (9)	0.0193 (4)
H1A	0.384 (2)	1.207 (4)	0.7547 (15)	0.044 (9)*
H4A	0.9161 (19)	−0.199 (4)	0.3751 (12)	0.017 (7)*
H5A	0.890 (2)	0.420 (3)	0.3983 (12)	0.016 (7)*
H2A	0.413 (3)	0.554 (5)	0.7422 (17)	0.053 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0182 (3)	0.0171 (3)	0.0209 (3)	0.0031 (2)	0.0009 (2)	0.0013 (2)
S2	0.0189 (3)	0.0176 (3)	0.0240 (3)	0.0032 (2)	0.0005 (2)	0.0011 (2)
O1	0.0181 (10)	0.0296 (11)	0.0220 (9)	0.0047 (8)	−0.0031 (7)	0.0024 (7)
O2	0.0272 (11)	0.0151 (9)	0.0320 (10)	0.0040 (8)	0.0058 (8)	0.0004 (7)
O3	0.0316 (12)	0.0502 (15)	0.0333 (11)	−0.0108 (11)	−0.0023 (9)	−0.0030 (9)
O4	0.070 (2)	0.090 (2)	0.0469 (15)	−0.0440 (18)	0.0051 (13)	−0.0351 (14)
O5	0.0189 (10)	0.0325 (12)	0.0254 (9)	0.0035 (8)	−0.0028 (7)	0.0023 (7)
O6	0.0298 (11)	0.0140 (9)	0.0371 (11)	0.0046 (7)	0.0045 (9)	0.0017 (7)
O7	0.0301 (13)	0.0669 (18)	0.0341 (12)	−0.0137 (11)	−0.0006 (9)	−0.0057 (10)
O8	0.070 (2)	0.101 (3)	0.0595 (18)	−0.0401 (19)	0.0026 (15)	−0.0462 (16)
N1	0.0251 (12)	0.0147 (11)	0.0208 (10)	0.0011 (9)	−0.0024 (9)	−0.0011 (8)
N2	0.0158 (11)	0.0135 (11)	0.0262 (10)	0.0016 (8)	0.0016 (8)	−0.0003 (8)
N3	0.0296 (14)	0.0409 (16)	0.0284 (12)	−0.0082 (12)	−0.0055 (10)	−0.0036 (11)
N4	0.0179 (11)	0.0147 (12)	0.0231 (10)	0.0026 (9)	−0.0016 (8)	0.0009 (7)
N5	0.0192 (12)	0.0144 (11)	0.0263 (11)	0.0003 (9)	0.0039 (8)	−0.0004 (8)
N6	0.0300 (15)	0.0478 (17)	0.0305 (13)	−0.0070 (13)	−0.0056 (11)	−0.0082 (11)
C1	0.0168 (12)	0.0138 (12)	0.0175 (11)	0.0007 (9)	0.0015 (9)	0.0000 (8)
C2	0.0146 (12)	0.0166 (12)	0.0207 (11)	−0.0010 (10)	−0.0031 (9)	0.0004 (9)
C3	0.0134 (12)	0.0205 (13)	0.0233 (12)	0.0026 (10)	0.0010 (9)	−0.0004 (9)
C4	0.0188 (13)	0.0196 (13)	0.0215 (11)	−0.0007 (10)	−0.0011 (10)	0.0000 (9)
C5	0.0193 (14)	0.0206 (14)	0.0216 (12)	0.0004 (10)	−0.0001 (10)	−0.0018 (9)
C6	0.0236 (13)	0.0184 (13)	0.0197 (11)	0.0041 (10)	−0.0008 (9)	0.0007 (9)
C7	0.0207 (14)	0.0209 (14)	0.0243 (12)	0.0011 (11)	−0.0001 (10)	−0.0006 (10)
C8	0.0233 (14)	0.0241 (14)	0.0290 (13)	−0.0010 (11)	0.0055 (11)	0.0020 (10)
C9	0.0329 (16)	0.0268 (15)	0.0239 (12)	0.0025 (12)	0.0048 (11)	0.0027 (10)
C10	0.0366 (18)	0.0333 (17)	0.0223 (14)	0.0011 (13)	−0.0035 (11)	−0.0054 (11)
C11	0.0202 (15)	0.0224 (14)	0.0252 (12)	−0.0001 (11)	−0.0015 (10)	−0.0053 (9)
C12	0.0236 (13)	0.0152 (12)	0.0150 (10)	0.0008 (10)	−0.0038 (9)	0.0017 (8)
C13	0.0179 (12)	0.0184 (13)	0.0180 (11)	−0.0005 (10)	0.0003 (9)	0.0004 (9)
C14	0.0236 (14)	0.0196 (13)	0.0187 (11)	0.0019 (11)	−0.0011 (9)	−0.0027 (9)
C15	0.0218 (14)	0.0196 (13)	0.0229 (12)	−0.0038 (10)	−0.0004 (10)	0.0000 (9)
C16	0.0159 (12)	0.0194 (13)	0.0217 (11)	−0.0005 (10)	−0.0002 (10)	0.0001 (9)
C17	0.0227 (13)	0.0173 (13)	0.0220 (12)	0.0044 (11)	0.0008 (9)	−0.0030 (9)
C18	0.0249 (14)	0.0207 (14)	0.0284 (13)	0.0010 (11)	0.0029 (11)	−0.0039 (10)
C19	0.0270 (15)	0.0246 (15)	0.0334 (14)	0.0008 (12)	0.0072 (11)	0.0002 (11)
C20	0.0361 (18)	0.0377 (19)	0.0270 (13)	0.0117 (14)	0.0054 (12)	0.0057 (11)
C21	0.0359 (18)	0.0425 (19)	0.0228 (13)	0.0043 (14)	−0.0046 (11)	−0.0037 (11)
C22	0.0276 (17)	0.0276 (15)	0.0273 (13)	−0.0009 (12)	0.0002 (11)	−0.0040 (10)
O9	0.0206 (10)	0.0199 (11)	0.0526 (12)	0.0062 (8)	0.0013 (9)	−0.0032 (8)
O10	0.0240 (11)	0.0164 (10)	0.0641 (14)	−0.0049 (8)	−0.0049 (10)	−0.0047 (9)
O11	0.0155 (10)	0.0191 (10)	0.0495 (12)	−0.0017 (8)	0.0039 (8)	−0.0025 (8)
N7	0.0179 (12)	0.0159 (11)	0.0255 (11)	−0.0003 (9)	−0.0007 (8)	−0.0014 (8)
O12	0.0231 (10)	0.0196 (10)	0.0341 (10)	−0.0052 (8)	−0.0010 (8)	0.0019 (7)
O13	0.0191 (10)	0.0188 (10)	0.0392 (11)	0.0021 (7)	0.0008 (8)	−0.0024 (8)
O14	0.0245 (10)	0.0203 (11)	0.0505 (13)	0.0047 (8)	0.0014 (9)	−0.0046 (8)
N8	0.0191 (11)	0.0188 (11)	0.0200 (10)	0.0003 (9)	−0.0028 (8)	0.0021 (8)

Geometric parameters (Å, º) top

S1—O2	1.4281 (19)	C6—C11	1.396 (4)
S1—O1	1.4284 (19)	C7—C8	1.391 (4)
S1—N2	1.636 (2)	C7—H7	0.9500
S1—C6	1.786 (2)	C8—C9	1.379 (4)
S2—O6	1.4275 (19)	C8—H8	0.9500
S2—O5	1.429 (2)	C9—C10	1.375 (4)
S2—N5	1.631 (2)	C9—H9	0.9500
S2—C17	1.792 (3)	C10—C11	1.385 (4)
O3—N3	1.223 (3)	C10—H10	0.9500
O4—N3	1.222 (3)	C12—C16	1.402 (4)
O7—N6	1.206 (3)	C12—C13	1.405 (4)
O8—N6	1.226 (4)	C13—C14	1.365 (4)
N1—C4	1.341 (3)	C13—H13	0.9500
N1—C3	1.351 (3)	C14—H14	0.9500
N1—H1A	1.06 (4)	C15—C16	1.361 (4)
N2—C1	1.389 (3)	C15—H15	0.9500
N2—H2A	0.97 (4)	C16—H16	0.9500
N3—C11	1.473 (4)	C17—C18	1.385 (4)
N4—C14	1.352 (4)	C17—C22	1.400 (4)
N4—C15	1.354 (3)	C18—C19	1.387 (4)
N4—H4A	0.90 (3)	C18—H18	0.9500
N5—C12	1.382 (3)	C19—C20	1.374 (4)
N5—H5A	0.94 (3)	C19—H19	0.9500
N6—C22	1.476 (4)	C20—C21	1.387 (4)
C1—C5	1.396 (3)	C20—H20	0.9500
C1—C2	1.403 (3)	C21—C22	1.379 (4)
C2—C3	1.366 (4)	C21—H21	0.9500
C2—H2	0.9500	O9—N7	1.245 (3)
C3—H3	0.9500	O10—N7	1.233 (3)
C4—C5	1.375 (3)	O11—N7	1.276 (3)
C4—H4	0.9500	O12—N8	1.248 (3)
C5—H5	0.9500	O13—N8	1.273 (3)
C6—C7	1.390 (4)	O14—N8	1.236 (3)

O2—S1—O1	119.72 (12)	C9—C8—C7	119.7 (3)
O2—S1—N2	104.89 (12)	C9—C8—H8	120.1
O1—S1—N2	109.10 (11)	C7—C8—H8	120.1
O2—S1—C6	109.71 (12)	C10—C9—C8	120.0 (2)
O1—S1—C6	105.54 (12)	C10—C9—H9	120.0
N2—S1—C6	107.38 (12)	C8—C9—H9	120.0
O6—S2—O5	120.17 (12)	C9—C10—C11	120.4 (3)
O6—S2—N5	105.37 (12)	C9—C10—H10	119.8
O5—S2—N5	108.65 (12)	C11—C10—H10	119.8
O6—S2—C17	109.44 (12)	C10—C11—C6	120.7 (3)
O5—S2—C17	105.61 (12)	C10—C11—N3	116.7 (2)
N5—S2—C17	106.99 (12)	C6—C11—N3	122.5 (2)
C4—N1—C3	121.1 (2)	N5—C12—C16	123.2 (2)
C4—N1—H1A	125.2 (19)	N5—C12—C13	118.0 (2)
C3—N1—H1A	113.6 (19)	C16—C12—C13	118.8 (2)
C1—N2—S1	126.18 (18)	C14—C13—C12	119.4 (2)
C1—N2—H2A	120 (2)	C14—C13—H13	120.3
S1—N2—H2A	113 (2)	C12—C13—H13	120.3
O4—N3—O3	124.0 (3)	N4—C14—C13	120.3 (2)
O4—N3—C11	117.3 (3)	N4—C14—H14	119.8
O3—N3—C11	118.6 (2)	C13—C14—H14	119.8
C14—N4—C15	121.6 (2)	N4—C15—C16	120.4 (2)
C14—N4—H4A	115.1 (18)	N4—C15—H15	119.8
C15—N4—H4A	123.4 (18)	C16—C15—H15	119.8
C12—N5—S2	127.28 (19)	C15—C16—C12	119.5 (2)
C12—N5—H5A	112.8 (17)	C15—C16—H16	120.2
S2—N5—H5A	117.9 (17)	C12—C16—H16	120.2
O7—N6—O8	124.1 (3)	C18—C17—C22	117.9 (2)
O7—N6—C22	119.4 (2)	C18—C17—S2	116.33 (18)
O8—N6—C22	116.5 (3)	C22—C17—S2	125.6 (2)
N2—C1—C5	123.0 (2)	C17—C18—C19	121.0 (2)
N2—C1—C2	117.4 (2)	C17—C18—H18	119.5
C5—C1—C2	119.6 (2)	C19—C18—H18	119.5
C3—C2—C1	118.6 (2)	C20—C19—C18	120.4 (3)
C3—C2—H2	120.7	C20—C19—H19	119.8
C1—C2—H2	120.7	C18—C19—H19	119.8
N1—C3—C2	121.1 (2)	C19—C20—C21	119.7 (3)
N1—C3—H3	119.5	C19—C20—H20	120.2
C2—C3—H3	119.5	C21—C20—H20	120.2
N1—C4—C5	120.8 (2)	C22—C21—C20	119.9 (3)
N1—C4—H4	119.6	C22—C21—H21	120.0
C5—C4—H4	119.6	C20—C21—H21	120.0
C4—C5—C1	118.7 (2)	C21—C22—C17	121.1 (3)
C4—C5—H5	120.6	C21—C22—N6	115.9 (3)
C1—C5—H5	120.6	C17—C22—N6	123.0 (2)
C7—C6—C11	118.0 (2)	O10—N7—O9	121.9 (2)
C7—C6—S1	116.03 (18)	O10—N7—O11	118.9 (2)
C11—C6—S1	125.7 (2)	O9—N7—O11	119.1 (2)
C6—C7—C8	121.1 (2)	O14—N8—O12	121.3 (2)
C6—C7—H7	119.5	O14—N8—O13	119.6 (2)
C8—C7—H7	119.5	O12—N8—O13	119.1 (2)

O2—S1—N2—C1	−169.3 (2)	O3—N3—C11—C10	−137.1 (3)
O1—S1—N2—C1	61.3 (2)	O4—N3—C11—C6	−141.4 (3)
C6—S1—N2—C1	−52.7 (2)	O3—N3—C11—C6	41.3 (4)
O6—S2—N5—C12	170.8 (2)	S2—N5—C12—C16	17.8 (3)
O5—S2—N5—C12	−59.2 (2)	S2—N5—C12—C13	−162.69 (19)
C17—S2—N5—C12	54.4 (2)	N5—C12—C13—C14	179.9 (2)
S1—N2—C1—C5	−16.3 (3)	C16—C12—C13—C14	−0.6 (3)
S1—N2—C1—C2	163.17 (18)	C15—N4—C14—C13	1.2 (3)
N2—C1—C2—C3	−177.3 (2)	C12—C13—C14—N4	−0.4 (3)
C5—C1—C2—C3	2.2 (3)	C14—N4—C15—C16	−1.0 (4)
C4—N1—C3—C2	−2.3 (4)	N4—C15—C16—C12	0.0 (3)
C1—C2—C3—N1	0.1 (3)	N5—C12—C16—C15	−179.8 (2)
C3—N1—C4—C5	2.0 (4)	C13—C12—C16—C15	0.8 (3)
N1—C4—C5—C1	0.4 (3)	O6—S2—C17—C18	133.3 (2)
N2—C1—C5—C4	177.0 (2)	O5—S2—C17—C18	2.6 (2)
C2—C1—C5—C4	−2.5 (3)	N5—S2—C17—C18	−113.0 (2)
O2—S1—C6—C7	−134.5 (2)	O6—S2—C17—C22	−41.5 (3)
O1—S1—C6—C7	−4.3 (2)	O5—S2—C17—C22	−172.2 (2)
N2—S1—C6—C7	112.0 (2)	N5—S2—C17—C22	72.2 (3)
O2—S1—C6—C11	39.3 (3)	C22—C17—C18—C19	−1.8 (4)
O1—S1—C6—C11	169.6 (2)	S2—C17—C18—C19	−177.1 (2)
N2—S1—C6—C11	−74.1 (3)	C17—C18—C19—C20	1.5 (4)
C11—C6—C7—C8	1.5 (4)	C18—C19—C20—C21	0.2 (4)
S1—C6—C7—C8	175.8 (2)	C19—C20—C21—C22	−1.5 (5)
C6—C7—C8—C9	−0.9 (4)	C20—C21—C22—C17	1.0 (5)
C7—C8—C9—C10	−0.3 (4)	C20—C21—C22—N6	−178.1 (3)
C8—C9—C10—C11	0.9 (4)	C18—C17—C22—C21	0.6 (4)
C9—C10—C11—C6	−0.3 (4)	S2—C17—C22—C21	175.3 (2)
C9—C10—C11—N3	178.1 (3)	C18—C17—C22—N6	179.6 (3)
C7—C6—C11—C10	−0.9 (4)	S2—C17—C22—N6	−5.6 (4)
S1—C6—C11—C10	−174.7 (2)	O7—N6—C22—C21	139.4 (3)
C7—C6—C11—N3	−179.2 (3)	O8—N6—C22—C21	−40.2 (4)
S1—C6—C11—N3	7.0 (4)	O7—N6—C22—C17	−39.7 (4)
O4—N3—C11—C10	40.2 (4)	O8—N6—C22—C17	140.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O11ⁱ	1.06 (4)	1.68 (4)	2.745 (3)	179 (3)
N1—H1A···O9ⁱ	1.06 (4)	2.65 (3)	3.361 (3)	124 (2)
N4—H4A···O13ⁱⁱ	0.90 (3)	1.85 (3)	2.737 (3)	171 (2)
N4—H4A···O12ⁱⁱ	0.90 (3)	2.68 (3)	3.273 (3)	124 (2)
N5—H5A···O13ⁱⁱⁱ	0.94 (3)	1.87 (3)	2.751 (3)	155 (2)
N2—H2A···O11^iv	0.97 (4)	1.78 (4)	2.725 (3)	166 (4)

Symmetry codes: (i) x−1/2, −y+3/2, z; (ii) −x+2, −y, z−1/2; (iii) −x+2, −y+1, z−1/2; (iv) x−1/2, −y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀N₃O₄S⁺·NO₃⁻
M_r	342.30
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	113
a, b, c (Å)	14.716 (3), 8.6671 (17), 21.941 (4)
V (Å³)	2798.5 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.20 × 0.16 × 0.02

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.943, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	20607, 5734, 5237
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.098, 1.04
No. of reflections	5734
No. of parameters	432
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.33
Absolute structure	Flack (1983), 2570 Friedel pairs
Absolute structure parameter	0.14 (6)

Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalStructure (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···O11ⁱ	1.06 (4)	1.68 (4)	2.745 (3)	179 (3)
N1—H1A···O9ⁱ	1.06 (4)	2.65 (3)	3.361 (3)	124 (2)
N4—H4A···O13ⁱⁱ	0.90 (3)	1.85 (3)	2.737 (3)	171 (2)
N4—H4A···O12ⁱⁱ	0.90 (3)	2.68 (3)	3.273 (3)	124 (2)
N5—H5A···O13ⁱⁱⁱ	0.94 (3)	1.87 (3)	2.751 (3)	155 (2)
N2—H2A···O11^iv	0.97 (4)	1.78 (4)	2.725 (3)	166 (4)

Symmetry codes: (i) x−1/2, −y+3/2, z; (ii) −x+2, −y, z−1/2; (iii) −x+2, −y+1, z−1/2; (iv) x−1/2, −y+1/2, z.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Damiano, T., Morton, D. & Nelson, A. (2007). Org. Biomol. Chem. 5, 2735—2752. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Li, J. S., Chen, L. G., Zhang, Y. Y., Xu, Y. J., Deng, Y. & Huang, P. M. (2007). J. Chem. Res. 6, 350–352. CrossRef Google Scholar
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yu, H.-J. & Li, J.-S. (2007). Acta Cryst. E63, o3399. CSD CrossRef IUCr Journals Google Scholar

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Volume 64| Part 12| December 2008| Page o2281

doi:10.1107/S1600536808035654

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