4-(2-Nitro-benzene-sulfonamido)pyridinium nitrate.

There are two mol-ecules in the asymmetric unit of the title compound, C(11)H(10)N(3)O(4)S(+)·NO(3) (-). 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 = 342.30

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.098

S = 1.04

5734 reflections

432 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.33 e Å−3

Absolute structure: Flack (1983 ▶), 2570 Friedel pairs

Flack parameter: 0.14 (6)

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035654/rk2115Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H10N3O4S+·NO3–	F000 = 1408
Mr = 342.30	Dx = 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 = 3.1–27.1º
b = 8.6671 (17) Å	µ = 0.28 mm−1
c = 21.941 (4) Å	T = 113 (2) K
V = 2798.5 (9) Å3	Block, colourless
Z = 8	0.20 × 0.16 × 0.02 mm

Rigaku Saturn CCD area-detector diffractometer	5734 independent reflections
Radiation source: Rotating anode	5237 reflections with I > 2σ(I)
Monochromator: Confocal	Rint = 0.046
Detector resolution: 7.31 pixels mm-1	θmax = 27.1º
T = 113(2) K	θmin = 3.3º
ω scans	h = −18→18
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)	k = −11→9
Tmin = 0.943, Tmax = 0.998	l = −20→28
20607 measured reflections

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(Fo2) + (0.0538P)2 + 0.0901P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.098	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.42 e Å−3
5734 reflections	Δρmin = −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	Flack parameter: 0.14 (6)

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···O11iv	0.97 (4)	1.78 (4)	2.725 (3)	166 (4)

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⋯O11iv	0.97 (4)	1.78 (4)	2.725 (3)	166 (4)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .