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Acta Cryst. (2008). E64, o2281    [ doi:10.1107/S1600536808035654 ]

4-(2-Nitrobenzenesulfonamido)pyridinium nitrate

L. Zhao and Q.-F. Yu

Abstract top

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 [pi]-electrons with those of the pyridinium ring. The crystal structure is stabilized by N-H...O hydrogen bonds.

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.

Refinement top

The N–bound H atoms were located in a difference map and refined isotropically. The C–bound H atoms were positioned geometrically (C—H = 0.95 Å) and refined as riding with Uiso(H) = 1.2Ueq(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
[Figure 1] 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
Mr = 342.30Dx = 1.625 Mg m−3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 8078 reflections
a = 14.716 (3) Åθ = 3.1–27.1°
b = 8.6671 (17) ŵ = 0.28 mm−1
c = 21.941 (4) ÅT = 113 K
V = 2798.5 (9) Å3Block, colourless
Z = 80.20 × 0.16 × 0.02 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		5734 independent reflections
Radiation source: Rotating anode5237 reflections with I > 2σ(I)
ConfocalRint = 0.046
Detector resolution: 7.31 pixels mm-1θmax = 27.1°, θmin = 3.3°
ω scansh = −18→18
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)		k = −11→9
Tmin = 0.943, Tmax = 0.998l = −20→28
20607 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: FullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.0538P)2 + 0.0901P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.098(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.42 e Å−3
5734 reflectionsΔρmin = −0.33 e Å−3
432 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0054 (7)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 2570 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.14 (6)
Crystal data top
C11H10N3O4S+·NO3−V = 2798.5 (9) Å3
Mr = 342.30Z = 8
Orthorhombic, Pna21Mo Kα radiation
a = 14.716 (3) ŵ = 0.28 mm−1
b = 8.6671 (17) ÅT = 113 K
c = 21.941 (4) Å0.20 × 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)
Tmin = 0.943, Tmax = 0.998Rint = 0.046
20607 measured reflectionsθmax = 27.1°
Refinement top
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098Δρmax = 0.42 e Å−3
S = 1.04Δρmin = −0.33 e Å−3
5734 reflectionsAbsolute structure: Flack (1983), 2570 Friedel pairs
432 parametersFlack 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
xyzUiso*/Ueq
S10.55489 (4)0.54735 (7)0.70897 (3)0.01874 (14)
S20.74559 (4)0.43842 (7)0.42871 (3)0.02018 (14)
O10.63055 (12)0.5867 (2)0.74667 (8)0.0233 (4)
O20.53170 (13)0.3890 (2)0.69999 (8)0.0248 (4)
O30.38958 (15)0.5302 (3)0.62281 (9)0.0384 (5)
O40.4342 (2)0.4321 (4)0.53747 (12)0.0689 (10)
O50.66949 (13)0.3918 (2)0.39273 (8)0.0256 (4)
O60.76670 (13)0.5983 (2)0.43544 (9)0.0270 (4)
O70.91479 (15)0.4690 (3)0.51112 (10)0.0437 (6)
O80.8745 (2)0.5660 (4)0.59706 (13)0.0769 (11)
N10.40728 (15)1.0904 (3)0.75443 (9)0.0202 (4)
N20.46295 (15)0.6264 (2)0.73697 (9)0.0185 (4)
N30.44496 (18)0.5160 (3)0.58163 (11)0.0330 (6)
N40.89765 (15)−0.1009 (3)0.37907 (9)0.0186 (4)
N50.83710 (16)0.3598 (3)0.40056 (9)0.0200 (5)
N60.86294 (19)0.4797 (3)0.55345 (11)0.0361 (6)
C10.44743 (16)0.7834 (3)0.74440 (10)0.0160 (5)
C20.35733 (17)0.8310 (3)0.75337 (10)0.0173 (5)
H20.30960.75760.75600.021*
C30.33974 (17)0.9853 (3)0.75823 (11)0.0191 (5)
H30.27901.01920.76440.023*
C40.49413 (18)1.0467 (3)0.74780 (11)0.0199 (5)
H40.54061.12270.74650.024*
C50.51674 (19)0.8933 (3)0.74283 (11)0.0205 (5)
H50.57840.86260.73840.025*
C60.57669 (18)0.6366 (3)0.63708 (11)0.0206 (5)
C70.65379 (17)0.7288 (3)0.63400 (11)0.0220 (5)
H70.68860.74620.66980.026*
C80.6808 (2)0.7962 (3)0.57937 (12)0.0255 (6)
H80.73310.86020.57810.031*
C90.6311 (2)0.7697 (3)0.52707 (12)0.0279 (6)
H90.64910.81590.48970.033*
C100.5556 (2)0.6764 (4)0.52898 (12)0.0307 (7)
H100.52210.65720.49280.037*
C110.52818 (19)0.6104 (3)0.58340 (12)0.0226 (5)
C120.85468 (17)0.2042 (3)0.39336 (10)0.0180 (5)
C130.94527 (17)0.1584 (3)0.38431 (10)0.0181 (5)
H130.99250.23310.38320.022*
C140.96478 (19)0.0056 (3)0.37715 (11)0.0206 (5)
H141.0258−0.02620.37080.025*
C150.80967 (19)−0.0599 (3)0.38700 (11)0.0214 (5)
H150.7638−0.13700.38750.026*
C160.78660 (18)0.0911 (3)0.39421 (11)0.0190 (5)
H160.72480.11960.39980.023*
C170.72784 (18)0.3544 (3)0.50237 (11)0.0207 (5)
C180.65166 (18)0.2619 (3)0.50870 (11)0.0247 (6)
H180.61410.24270.47430.030*
C190.6294 (2)0.1970 (3)0.56452 (12)0.0283 (6)
H190.57770.13200.56780.034*
C200.6817 (2)0.2263 (4)0.61506 (13)0.0336 (7)
H200.66640.18140.65320.040*
C210.7570 (2)0.3217 (4)0.61016 (13)0.0337 (7)
H210.79260.34430.64520.040*
C220.7801 (2)0.3839 (3)0.55443 (12)0.0275 (6)
O90.71160 (13)0.2133 (2)0.76947 (9)0.0310 (5)
O100.72427 (15)−0.0296 (2)0.74762 (11)0.0348 (5)
O110.84491 (13)0.1111 (2)0.75566 (10)0.0280 (4)
N70.75865 (15)0.0975 (2)0.75795 (10)0.0198 (5)
O120.91094 (12)0.2926 (2)0.88498 (8)0.0256 (4)
O131.04400 (13)0.4007 (2)0.88032 (9)0.0257 (4)
O140.92515 (15)0.5367 (2)0.90341 (10)0.0318 (5)
N80.95891 (15)0.4105 (2)0.89013 (9)0.0193 (4)
H1A0.384 (2)1.207 (4)0.7547 (15)0.044 (9)*
H4A0.9161 (19)−0.199 (4)0.3751 (12)0.017 (7)*
H5A0.890 (2)0.420 (3)0.3983 (12)0.016 (7)*
H2A0.413 (3)0.554 (5)0.7422 (17)0.053 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0182 (3)0.0171 (3)0.0209 (3)0.0031 (2)0.0009 (2)0.0013 (2)
S20.0189 (3)0.0176 (3)0.0240 (3)0.0032 (2)0.0005 (2)0.0011 (2)
O10.0181 (10)0.0296 (11)0.0220 (9)0.0047 (8)−0.0031 (7)0.0024 (7)
O20.0272 (11)0.0151 (9)0.0320 (10)0.0040 (8)0.0058 (8)0.0004 (7)
O30.0316 (12)0.0502 (15)0.0333 (11)−0.0108 (11)−0.0023 (9)−0.0030 (9)
O40.070 (2)0.090 (2)0.0469 (15)−0.0440 (18)0.0051 (13)−0.0351 (14)
O50.0189 (10)0.0325 (12)0.0254 (9)0.0035 (8)−0.0028 (7)0.0023 (7)
O60.0298 (11)0.0140 (9)0.0371 (11)0.0046 (7)0.0045 (9)0.0017 (7)
O70.0301 (13)0.0669 (18)0.0341 (12)−0.0137 (11)−0.0006 (9)−0.0057 (10)
O80.070 (2)0.101 (3)0.0595 (18)−0.0401 (19)0.0026 (15)−0.0462 (16)
N10.0251 (12)0.0147 (11)0.0208 (10)0.0011 (9)−0.0024 (9)−0.0011 (8)
N20.0158 (11)0.0135 (11)0.0262 (10)0.0016 (8)0.0016 (8)−0.0003 (8)
N30.0296 (14)0.0409 (16)0.0284 (12)−0.0082 (12)−0.0055 (10)−0.0036 (11)
N40.0179 (11)0.0147 (12)0.0231 (10)0.0026 (9)−0.0016 (8)0.0009 (7)
N50.0192 (12)0.0144 (11)0.0263 (11)0.0003 (9)0.0039 (8)−0.0004 (8)
N60.0300 (15)0.0478 (17)0.0305 (13)−0.0070 (13)−0.0056 (11)−0.0082 (11)
C10.0168 (12)0.0138 (12)0.0175 (11)0.0007 (9)0.0015 (9)0.0000 (8)
C20.0146 (12)0.0166 (12)0.0207 (11)−0.0010 (10)−0.0031 (9)0.0004 (9)
C30.0134 (12)0.0205 (13)0.0233 (12)0.0026 (10)0.0010 (9)−0.0004 (9)
C40.0188 (13)0.0196 (13)0.0215 (11)−0.0007 (10)−0.0011 (10)0.0000 (9)
C50.0193 (14)0.0206 (14)0.0216 (12)0.0004 (10)−0.0001 (10)−0.0018 (9)
C60.0236 (13)0.0184 (13)0.0197 (11)0.0041 (10)−0.0008 (9)0.0007 (9)
C70.0207 (14)0.0209 (14)0.0243 (12)0.0011 (11)−0.0001 (10)−0.0006 (10)
C80.0233 (14)0.0241 (14)0.0290 (13)−0.0010 (11)0.0055 (11)0.0020 (10)
C90.0329 (16)0.0268 (15)0.0239 (12)0.0025 (12)0.0048 (11)0.0027 (10)
C100.0366 (18)0.0333 (17)0.0223 (14)0.0011 (13)−0.0035 (11)−0.0054 (11)
C110.0202 (15)0.0224 (14)0.0252 (12)−0.0001 (11)−0.0015 (10)−0.0053 (9)
C120.0236 (13)0.0152 (12)0.0150 (10)0.0008 (10)−0.0038 (9)0.0017 (8)
C130.0179 (12)0.0184 (13)0.0180 (11)−0.0005 (10)0.0003 (9)0.0004 (9)
C140.0236 (14)0.0196 (13)0.0187 (11)0.0019 (11)−0.0011 (9)−0.0027 (9)
C150.0218 (14)0.0196 (13)0.0229 (12)−0.0038 (10)−0.0004 (10)0.0000 (9)
C160.0159 (12)0.0194 (13)0.0217 (11)−0.0005 (10)−0.0002 (10)0.0001 (9)
C170.0227 (13)0.0173 (13)0.0220 (12)0.0044 (11)0.0008 (9)−0.0030 (9)
C180.0249 (14)0.0207 (14)0.0284 (13)0.0010 (11)0.0029 (11)−0.0039 (10)
C190.0270 (15)0.0246 (15)0.0334 (14)0.0008 (12)0.0072 (11)0.0002 (11)
C200.0361 (18)0.0377 (19)0.0270 (13)0.0117 (14)0.0054 (12)0.0057 (11)
C210.0359 (18)0.0425 (19)0.0228 (13)0.0043 (14)−0.0046 (11)−0.0037 (11)
C220.0276 (17)0.0276 (15)0.0273 (13)−0.0009 (12)0.0002 (11)−0.0040 (10)
O90.0206 (10)0.0199 (11)0.0526 (12)0.0062 (8)0.0013 (9)−0.0032 (8)
O100.0240 (11)0.0164 (10)0.0641 (14)−0.0049 (8)−0.0049 (10)−0.0047 (9)
O110.0155 (10)0.0191 (10)0.0495 (12)−0.0017 (8)0.0039 (8)−0.0025 (8)
N70.0179 (12)0.0159 (11)0.0255 (11)−0.0003 (9)−0.0007 (8)−0.0014 (8)
O120.0231 (10)0.0196 (10)0.0341 (10)−0.0052 (8)−0.0010 (8)0.0019 (7)
O130.0191 (10)0.0188 (10)0.0392 (11)0.0021 (7)0.0008 (8)−0.0024 (8)
O140.0245 (10)0.0203 (11)0.0505 (13)0.0047 (8)0.0014 (9)−0.0046 (8)
N80.0191 (11)0.0188 (11)0.0200 (10)0.0003 (9)−0.0028 (8)0.0021 (8)
Geometric parameters (Å, °) top
S1—O21.4281 (19)C6—C111.396 (4)
S1—O11.4284 (19)C7—C81.391 (4)
S1—N21.636 (2)C7—H70.9500
S1—C61.786 (2)C8—C91.379 (4)
S2—O61.4275 (19)C8—H80.9500
S2—O51.429 (2)C9—C101.375 (4)
S2—N51.631 (2)C9—H90.9500
S2—C171.792 (3)C10—C111.385 (4)
O3—N31.223 (3)C10—H100.9500
O4—N31.222 (3)C12—C161.402 (4)
O7—N61.206 (3)C12—C131.405 (4)
O8—N61.226 (4)C13—C141.365 (4)
N1—C41.341 (3)C13—H130.9500
N1—C31.351 (3)C14—H140.9500
N1—H1A1.06 (4)C15—C161.361 (4)
N2—C11.389 (3)C15—H150.9500
N2—H2A0.97 (4)C16—H160.9500
N3—C111.473 (4)C17—C181.385 (4)
N4—C141.352 (4)C17—C221.400 (4)
N4—C151.354 (3)C18—C191.387 (4)
N4—H4A0.90 (3)C18—H180.9500
N5—C121.382 (3)C19—C201.374 (4)
N5—H5A0.94 (3)C19—H190.9500
N6—C221.476 (4)C20—C211.387 (4)
C1—C51.396 (3)C20—H200.9500
C1—C21.403 (3)C21—C221.379 (4)
C2—C31.366 (4)C21—H210.9500
C2—H20.9500O9—N71.245 (3)
C3—H30.9500O10—N71.233 (3)
C4—C51.375 (3)O11—N71.276 (3)
C4—H40.9500O12—N81.248 (3)
C5—H50.9500O13—N81.273 (3)
C6—C71.390 (4)O14—N81.236 (3)
O2—S1—O1119.72 (12)C9—C8—C7119.7 (3)
O2—S1—N2104.89 (12)C9—C8—H8120.1
O1—S1—N2109.10 (11)C7—C8—H8120.1
O2—S1—C6109.71 (12)C10—C9—C8120.0 (2)
O1—S1—C6105.54 (12)C10—C9—H9120.0
N2—S1—C6107.38 (12)C8—C9—H9120.0
O6—S2—O5120.17 (12)C9—C10—C11120.4 (3)
O6—S2—N5105.37 (12)C9—C10—H10119.8
O5—S2—N5108.65 (12)C11—C10—H10119.8
O6—S2—C17109.44 (12)C10—C11—C6120.7 (3)
O5—S2—C17105.61 (12)C10—C11—N3116.7 (2)
N5—S2—C17106.99 (12)C6—C11—N3122.5 (2)
C4—N1—C3121.1 (2)N5—C12—C16123.2 (2)
C4—N1—H1A125.2 (19)N5—C12—C13118.0 (2)
C3—N1—H1A113.6 (19)C16—C12—C13118.8 (2)
C1—N2—S1126.18 (18)C14—C13—C12119.4 (2)
C1—N2—H2A120 (2)C14—C13—H13120.3
S1—N2—H2A113 (2)C12—C13—H13120.3
O4—N3—O3124.0 (3)N4—C14—C13120.3 (2)
O4—N3—C11117.3 (3)N4—C14—H14119.8
O3—N3—C11118.6 (2)C13—C14—H14119.8
C14—N4—C15121.6 (2)N4—C15—C16120.4 (2)
C14—N4—H4A115.1 (18)N4—C15—H15119.8
C15—N4—H4A123.4 (18)C16—C15—H15119.8
C12—N5—S2127.28 (19)C15—C16—C12119.5 (2)
C12—N5—H5A112.8 (17)C15—C16—H16120.2
S2—N5—H5A117.9 (17)C12—C16—H16120.2
O7—N6—O8124.1 (3)C18—C17—C22117.9 (2)
O7—N6—C22119.4 (2)C18—C17—S2116.33 (18)
O8—N6—C22116.5 (3)C22—C17—S2125.6 (2)
N2—C1—C5123.0 (2)C17—C18—C19121.0 (2)
N2—C1—C2117.4 (2)C17—C18—H18119.5
C5—C1—C2119.6 (2)C19—C18—H18119.5
C3—C2—C1118.6 (2)C20—C19—C18120.4 (3)
C3—C2—H2120.7C20—C19—H19119.8
C1—C2—H2120.7C18—C19—H19119.8
N1—C3—C2121.1 (2)C19—C20—C21119.7 (3)
N1—C3—H3119.5C19—C20—H20120.2
C2—C3—H3119.5C21—C20—H20120.2
N1—C4—C5120.8 (2)C22—C21—C20119.9 (3)
N1—C4—H4119.6C22—C21—H21120.0
C5—C4—H4119.6C20—C21—H21120.0
C4—C5—C1118.7 (2)C21—C22—C17121.1 (3)
C4—C5—H5120.6C21—C22—N6115.9 (3)
C1—C5—H5120.6C17—C22—N6123.0 (2)
C7—C6—C11118.0 (2)O10—N7—O9121.9 (2)
C7—C6—S1116.03 (18)O10—N7—O11118.9 (2)
C11—C6—S1125.7 (2)O9—N7—O11119.1 (2)
C6—C7—C8121.1 (2)O14—N8—O12121.3 (2)
C6—C7—H7119.5O14—N8—O13119.6 (2)
C8—C7—H7119.5O12—N8—O13119.1 (2)
O2—S1—N2—C1−169.3 (2)O3—N3—C11—C10−137.1 (3)
O1—S1—N2—C161.3 (2)O4—N3—C11—C6−141.4 (3)
C6—S1—N2—C1−52.7 (2)O3—N3—C11—C641.3 (4)
O6—S2—N5—C12170.8 (2)S2—N5—C12—C1617.8 (3)
O5—S2—N5—C12−59.2 (2)S2—N5—C12—C13−162.69 (19)
C17—S2—N5—C1254.4 (2)N5—C12—C13—C14179.9 (2)
S1—N2—C1—C5−16.3 (3)C16—C12—C13—C14−0.6 (3)
S1—N2—C1—C2163.17 (18)C15—N4—C14—C131.2 (3)
N2—C1—C2—C3−177.3 (2)C12—C13—C14—N4−0.4 (3)
C5—C1—C2—C32.2 (3)C14—N4—C15—C16−1.0 (4)
C4—N1—C3—C2−2.3 (4)N4—C15—C16—C120.0 (3)
C1—C2—C3—N10.1 (3)N5—C12—C16—C15−179.8 (2)
C3—N1—C4—C52.0 (4)C13—C12—C16—C150.8 (3)
N1—C4—C5—C10.4 (3)O6—S2—C17—C18133.3 (2)
N2—C1—C5—C4177.0 (2)O5—S2—C17—C182.6 (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—C7112.0 (2)N5—S2—C17—C2272.2 (3)
O2—S1—C6—C1139.3 (3)C22—C17—C18—C19−1.8 (4)
O1—S1—C6—C11169.6 (2)S2—C17—C18—C19−177.1 (2)
N2—S1—C6—C11−74.1 (3)C17—C18—C19—C201.5 (4)
C11—C6—C7—C81.5 (4)C18—C19—C20—C210.2 (4)
S1—C6—C7—C8175.8 (2)C19—C20—C21—C22−1.5 (5)
C6—C7—C8—C9−0.9 (4)C20—C21—C22—C171.0 (5)
C7—C8—C9—C10−0.3 (4)C20—C21—C22—N6−178.1 (3)
C8—C9—C10—C110.9 (4)C18—C17—C22—C210.6 (4)
C9—C10—C11—C6−0.3 (4)S2—C17—C22—C21175.3 (2)
C9—C10—C11—N3178.1 (3)C18—C17—C22—N6179.6 (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—C21139.4 (3)
C7—C6—C11—N3−179.2 (3)O8—N6—C22—C21−40.2 (4)
S1—C6—C11—N37.0 (4)O7—N6—C22—C17−39.7 (4)
O4—N3—C11—C1040.2 (4)O8—N6—C22—C17140.7 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O11i1.06 (4)1.68 (4)2.745 (3)179 (3)
N1—H1A···O9i1.06 (4)2.65 (3)3.361 (3)124 (2)
N4—H4A···O13ii0.90 (3)1.85 (3)2.737 (3)171 (2)
N4—H4A···O12ii0.90 (3)2.68 (3)3.273 (3)124 (2)
N5—H5A···O13iii0.94 (3)1.87 (3)2.751 (3)155 (2)
N2—H2A···O11iv0.97 (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.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O11i1.06 (4)1.68 (4)2.745 (3)179 (3)
N1—H1A···O9i1.06 (4)2.65 (3)3.361 (3)124 (2)
N4—H4A···O13ii0.90 (3)1.85 (3)2.737 (3)171 (2)
N4—H4A···O12ii0.90 (3)2.68 (3)3.273 (3)124 (2)
N5—H5A···O13iii0.94 (3)1.87 (3)2.751 (3)155 (2)
N2—H2A···O11iv0.97 (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
References top

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Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Li, J. S., Chen, L. G., Zhang, Y. Y., Xu, Y. J., Deng, Y. & Huang, P. M. (2007). J. Chem. Res. 6, 350–352.

Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Yu, H.-J. & Li, J.-S. (2007). Acta Cryst. E63, o3399.