4-(2-Nitrobenzenesulfonamido)pyridinium nitrate (2024)

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Acta Cryst. (2008). E64, o2281
https://doi.org/10.1107/S1600536808035654

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L. Zhao and Q.-F. Yu

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—HO hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808035654/rk2115sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808035654/rk2115Isup2.hkl Contains datablock I

CCDC reference: 712395

checkCIF report

Key indicators

Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.004 Å
R factor = 0.040
wR factor = 0.098
Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors foundAlert level C Value of measurement temperature given = 113.000 Value of melting point given = 0.000PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.97 RatioPLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.00 RatioPLAT353_ALERT_3_C Long N-H Bond (0.87A) N1 - H1A ... 1.07 Ang.PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A .. O9 .. 2.65 Ang.PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A .. O12 .. 2.68 Ang.Alert level GREFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.10 From the CIF: _reflns_number_total 5734 Count of symmetry unique reflns 3164 Completeness (_total/calc) 181.23% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2570 Fraction of Friedel pairs measured 0.812 Are heavy atom types Z>Si present yesPLAT033_ALERT_4_G Flack Parameter Value Deviates from Zero ....... 0.14 0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Organic pyridinium salts have been widely used in the construction ofsupramolecular architectures (Damiano et al., 2007). As part ofourongoing studies of supramolecular chemistry involving the pyridinium rings(Li et al., 2007), the structure of the title compound wasdeterminedby X–ray diffraction. In the cations of the title compound the short C–Ndistance [N2–C1 = 1.389(3)Å and N5–C12 = 1.382(3)Å] has a valuebetween those of a typical C═N double and C—N single bond (1.47–1.50Åand 1.34–1.38Å, respectively; Allen et al., 1987). Thismight beindicative of a slight conjugation of the N sulfonamide π–electrons withthose of the pyridinium ring. In the two symmetry–independent molecules(Fig. 1), the dihedral angles between the benzene ring and the pyridinium ringare 85.1(1)° and 86.2(1)° respectively. The dihedral angles between thenitro–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 etal. (2007); Yu & Li (2007). Damiano et al.(2007) describe the useof pyridinium derivatives for the construction of supramoleculararchitectures.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 reactionmixture was stirred overnight. The yellow solid obtained was washed with warmwater to obtain the title compound in a yield of 52.9%. A colourless singlecrystals, suitable for X–ray analysis were obtained by slow evaporation of annitric acid (10%) solution at room temperature over a period of a week.

Refinement top

The N–bound H atoms were located in a difference map and refinedisotropically. The C–bound H atoms were positioned geometrically(C—H = 0.95 Å) and refined as riding withU_iso(H) = 1.2U_eq(C).

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 twosymmetry-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

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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

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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

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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

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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

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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

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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

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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)

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	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)

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	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)

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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).