2-Nitro-N-(4-pyridinio)benzene-sulfonamidate monohydrate.

The title compound, C(11)H(9)N(3)O(4)S·H(2)O, contains both an acid and a base centre and displays a zwitterionic structure. There are two independent mol-ecules and two water mol-ecules in the asymmetric unit. The dihedral angles between the benzene ring and the pyridinium ring are 109.7 (1) and 110.7 (1)°. The dihedral angles between the nitro group and the benzene ring are 116.1 (2) and 116.7 (1)°. The crystal structure is stabilized by N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds.

Related literature

For the uses of organic pyridinium salts, see: Damiano et al. (2007 ▶). For zwitterionic forms of N-aryl­benzene­sulfonamides, see: Li et al. (2007 ▶); Yu & Li (2007 ▶). For reference geometric data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H9N3O4S·H2O

M = 297.29

Monoclinic,

a = 8.7206 (17) Å

b = 11.972 (2) Å

c = 12.743 (3) Å

β = 107.65 (3)°

V = 1267.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 113 (2) K

0.14 × 0.10 × 0.04 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.962, T max = 0.989

10348 measured reflections

4633 independent reflections

3587 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.090

S = 1.03

4633 reflections

385 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.40 e Å−3

Absolute structure: Flack (1983 ▶), 1560 Friedel pairs

Flack parameter: 0.52 (6)

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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035526/hg2431sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035526/hg2431Isup2.hkl

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

C11H9N3O4S·H2O	F000 = 616
Mr = 297.29	Dx = 1.557 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4439 reflections
a = 8.7206 (17) Å	θ = 2.4–27.5º
b = 11.972 (2) Å	µ = 0.28 mm−1
c = 12.743 (3) Å	T = 113 (2) K
β = 107.65 (3)º	Block, colourless
V = 1267.8 (4) Å3	0.14 × 0.10 × 0.04 mm
Z = 4

Rigaku Saturn diffractometer	4633 independent reflections
Radiation source: rotating anode	3587 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.033
T = 113(2) K	θmax = 27.5º
ω scans	θmin = 1.7º
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)	h = −11→11
Tmin = 0.962, Tmax = 0.989	k = −12→15
10348 measured reflections	l = −16→16

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)] = 0.032	w = 1/[σ2(Fo2) + (0.0539P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.090	(Δ/σ)max = 0.002
S = 1.03	Δρmax = 0.22 e Å−3
4633 reflections	Δρmin = −0.40 e Å−3
385 parameters	Extinction correction: none
9 restraints	Absolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.52 (6)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
S1	0.54299 (7)	0.49945 (5)	0.75574 (5)	0.01423 (14)
S2	1.01577 (7)	0.25356 (5)	0.35546 (5)	0.01307 (14)
O1	0.36887 (19)	0.49815 (17)	0.72910 (14)	0.0177 (4)
O2	0.6116 (2)	0.59540 (15)	0.71745 (16)	0.0187 (4)
O3	0.4219 (3)	0.29003 (18)	0.87441 (18)	0.0318 (5)
O4	0.2777 (2)	0.4008 (2)	0.94108 (18)	0.0326 (5)
O5	0.9524 (2)	0.15286 (15)	0.38857 (15)	0.0165 (4)
O6	1.1904 (2)	0.26159 (18)	0.38501 (16)	0.0182 (4)
O7	1.1373 (3)	0.46983 (18)	0.24125 (19)	0.0334 (5)
O8	1.2807 (2)	0.3638 (2)	0.16880 (18)	0.0371 (6)
N1	1.0324 (3)	0.2999 (2)	0.67719 (19)	0.0185 (5)
N2	0.5920 (2)	0.38299 (18)	0.71702 (19)	0.0146 (5)
N3	0.4050 (3)	0.3727 (2)	0.9245 (2)	0.0217 (5)
N4	0.5077 (3)	0.4240 (2)	0.43389 (18)	0.0179 (5)
N5	0.9564 (2)	0.36491 (18)	0.39696 (18)	0.0141 (5)
N6	1.1564 (3)	0.3888 (2)	0.18846 (19)	0.0230 (6)
C1	0.7414 (3)	0.3615 (2)	0.7078 (2)	0.0132 (5)
C2	0.7644 (3)	0.2549 (2)	0.6690 (2)	0.0167 (5)
H2	0.6813	0.2029	0.6537	0.020*
C3	0.9100 (3)	0.2265 (2)	0.6532 (2)	0.0188 (6)
H3	0.9231	0.1563	0.6259	0.023*
C4	1.0168 (3)	0.4019 (2)	0.7153 (2)	0.0179 (6)
H4	1.1030	0.4513	0.7304	0.021*
C5	0.8752 (3)	0.4350 (2)	0.7325 (2)	0.0169 (6)
H5	0.8672	0.5058	0.7604	0.020*
C6	0.6158 (3)	0.5053 (3)	0.9027 (2)	0.0148 (5)
C7	0.7441 (3)	0.5753 (2)	0.9531 (2)	0.0189 (6)
H7	0.7936	0.6156	0.9100	0.023*
C8	0.7996 (3)	0.5858 (2)	1.0674 (2)	0.0240 (6)
H8	0.8857	0.6329	1.0999	0.029*
C9	0.7271 (3)	0.5264 (3)	1.1326 (2)	0.0245 (7)
H9	0.7656	0.5325	1.2089	0.029*
C10	0.5978 (3)	0.4582 (2)	1.0843 (2)	0.0208 (6)
H10	0.5469	0.4197	1.1277	0.025*
C11	0.5441 (3)	0.4472 (2)	0.9712 (2)	0.0162 (6)
C12	0.8049 (3)	0.3782 (2)	0.4049 (2)	0.0120 (5)
C13	0.7734 (3)	0.4806 (2)	0.4510 (2)	0.0163 (6)
H13	0.8534	0.5347	0.4722	0.020*
C14	0.6264 (3)	0.4998 (2)	0.4642 (2)	0.0181 (5)
H14	0.6078	0.5669	0.4949	0.022*
C15	0.5302 (3)	0.3265 (2)	0.3884 (2)	0.0165 (5)
H15	0.4464	0.2752	0.3672	0.020*
C16	0.6767 (3)	0.3014 (2)	0.3725 (2)	0.0136 (5)
H16	0.6905	0.2339	0.3405	0.016*
C17	0.9459 (3)	0.2526 (2)	0.2084 (2)	0.0145 (5)
C18	0.8167 (3)	0.1850 (2)	0.1552 (2)	0.0179 (6)
H18	0.7672	0.1423	0.1967	0.021*
C19	0.7603 (3)	0.1799 (2)	0.0417 (2)	0.0229 (6)
H19	0.6723	0.1349	0.0080	0.027*
C20	0.8324 (3)	0.2406 (3)	−0.0223 (2)	0.0245 (7)
H20	0.7933	0.2365	−0.0987	0.029*
C21	0.9631 (3)	0.3074 (2)	0.0276 (2)	0.0195 (6)
H21	1.0141	0.3476	−0.0146	0.023*
C22	1.0173 (3)	0.3137 (2)	0.1415 (2)	0.0157 (6)
O9	0.2408 (2)	0.50194 (18)	0.48520 (16)	0.0183 (4)
O10	0.6923 (2)	0.74683 (18)	0.37557 (18)	0.0203 (4)
H1A	1.127 (3)	0.280 (3)	0.665 (3)	0.054 (11)*
H4A	0.411 (2)	0.441 (2)	0.444 (2)	0.021 (8)*
H9A	0.260 (3)	0.500 (3)	0.5558 (8)	0.047 (11)*
H9B	0.160 (2)	0.460 (2)	0.4517 (18)	0.024 (9)*
H10A	0.719 (4)	0.751 (4)	0.4468 (8)	0.11 (2)*
H10B	0.601 (2)	0.780 (3)	0.346 (2)	0.034 (10)*

	U11	U22	U33	U12	U13	U23
S1	0.0127 (3)	0.0152 (3)	0.0156 (3)	0.0016 (3)	0.0055 (2)	0.0026 (3)
S2	0.0098 (3)	0.0162 (3)	0.0138 (3)	0.0013 (3)	0.0044 (2)	0.0012 (3)
O1	0.0119 (8)	0.0220 (10)	0.0201 (10)	0.0049 (9)	0.0064 (7)	0.0009 (9)
O2	0.0242 (10)	0.0133 (9)	0.0209 (11)	0.0000 (8)	0.0102 (9)	0.0042 (8)
O3	0.0376 (12)	0.0285 (12)	0.0288 (13)	−0.0115 (10)	0.0095 (10)	−0.0019 (10)
O4	0.0157 (9)	0.0515 (15)	0.0329 (13)	−0.0051 (10)	0.0109 (9)	0.0064 (12)
O5	0.0194 (10)	0.0153 (9)	0.0158 (10)	0.0043 (8)	0.0067 (8)	0.0053 (8)
O6	0.0099 (8)	0.0269 (11)	0.0190 (10)	0.0008 (9)	0.0061 (7)	0.0016 (9)
O7	0.0378 (13)	0.0292 (13)	0.0329 (13)	−0.0111 (10)	0.0101 (11)	−0.0060 (10)
O8	0.0180 (10)	0.0689 (18)	0.0274 (13)	−0.0077 (11)	0.0114 (10)	0.0055 (12)
N1	0.0135 (11)	0.0249 (12)	0.0184 (12)	0.0064 (10)	0.0067 (9)	0.0022 (10)
N2	0.0116 (10)	0.0147 (11)	0.0196 (12)	0.0000 (9)	0.0078 (9)	−0.0001 (9)
N3	0.0209 (12)	0.0263 (14)	0.0176 (13)	−0.0040 (11)	0.0057 (10)	0.0071 (10)
N4	0.0148 (11)	0.0224 (13)	0.0179 (12)	0.0020 (10)	0.0072 (9)	0.0009 (10)
N5	0.0108 (10)	0.0177 (11)	0.0144 (11)	−0.0028 (9)	0.0046 (9)	−0.0035 (9)
N6	0.0193 (12)	0.0354 (15)	0.0146 (12)	−0.0067 (11)	0.0054 (10)	0.0064 (11)
C1	0.0123 (11)	0.0178 (13)	0.0100 (13)	0.0024 (10)	0.0042 (10)	0.0041 (10)
C2	0.0166 (11)	0.0179 (12)	0.0164 (13)	−0.0044 (12)	0.0062 (10)	0.0015 (12)
C3	0.0177 (13)	0.0173 (14)	0.0217 (15)	0.0033 (11)	0.0062 (11)	−0.0025 (11)
C4	0.0133 (12)	0.0214 (14)	0.0181 (14)	−0.0009 (11)	0.0035 (10)	0.0014 (12)
C5	0.0145 (12)	0.0147 (13)	0.0211 (15)	0.0009 (11)	0.0048 (11)	−0.0006 (11)
C6	0.0151 (12)	0.0134 (13)	0.0166 (13)	0.0032 (12)	0.0059 (10)	0.0000 (12)
C7	0.0206 (13)	0.0143 (13)	0.0224 (15)	−0.0036 (11)	0.0075 (12)	0.0006 (11)
C8	0.0252 (15)	0.0225 (15)	0.0224 (16)	−0.0067 (13)	0.0040 (13)	−0.0035 (12)
C9	0.0255 (14)	0.0278 (16)	0.0184 (15)	0.0041 (13)	0.0038 (12)	−0.0030 (12)
C10	0.0236 (14)	0.0239 (15)	0.0178 (15)	0.0041 (12)	0.0106 (12)	0.0047 (12)
C11	0.0103 (11)	0.0175 (13)	0.0217 (15)	0.0013 (10)	0.0062 (11)	0.0027 (11)
C12	0.0152 (12)	0.0125 (12)	0.0083 (12)	0.0024 (10)	0.0038 (10)	0.0017 (10)
C13	0.0168 (12)	0.0141 (13)	0.0183 (14)	−0.0048 (11)	0.0060 (11)	−0.0026 (11)
C14	0.0225 (13)	0.0147 (12)	0.0186 (13)	−0.0018 (12)	0.0087 (11)	−0.0020 (12)
C15	0.0136 (12)	0.0198 (13)	0.0173 (14)	0.0002 (11)	0.0066 (11)	−0.0031 (11)
C16	0.0093 (11)	0.0150 (12)	0.0173 (14)	−0.0026 (10)	0.0051 (10)	−0.0032 (11)
C17	0.0160 (12)	0.0150 (12)	0.0119 (13)	0.0007 (12)	0.0033 (10)	−0.0004 (11)
C18	0.0193 (13)	0.0163 (14)	0.0198 (15)	−0.0015 (12)	0.0084 (12)	0.0037 (12)
C19	0.0262 (15)	0.0190 (15)	0.0202 (15)	−0.0061 (13)	0.0022 (12)	0.0005 (12)
C20	0.0322 (15)	0.0275 (16)	0.0115 (14)	0.0032 (14)	0.0033 (12)	−0.0006 (13)
C21	0.0193 (13)	0.0221 (15)	0.0205 (15)	0.0031 (12)	0.0110 (12)	0.0049 (12)
C22	0.0118 (11)	0.0181 (14)	0.0172 (14)	0.0001 (11)	0.0045 (11)	0.0019 (11)
O9	0.0157 (9)	0.0210 (10)	0.0194 (11)	0.0003 (9)	0.0072 (8)	−0.0056 (10)
O10	0.0170 (9)	0.0221 (10)	0.0215 (11)	0.0022 (9)	0.0057 (8)	0.0043 (10)

S1—O2	1.4464 (19)	C6—C11	1.403 (3)
S1—O1	1.4521 (17)	C7—C8	1.394 (4)
S1—N2	1.581 (2)	C7—H7	0.9300
S1—C6	1.787 (3)	C8—C9	1.383 (4)
S2—O5	1.4416 (19)	C8—H8	0.9300
S2—O6	1.4568 (17)	C9—C10	1.377 (4)
S2—N5	1.578 (2)	C9—H9	0.9300
S2—C17	1.787 (3)	C10—C11	1.380 (4)
O3—N3	1.211 (3)	C10—H10	0.9300
O4—N3	1.237 (3)	C12—C16	1.409 (3)
O7—N6	1.221 (3)	C12—C13	1.421 (3)
O8—N6	1.221 (3)	C13—C14	1.362 (3)
N1—C4	1.336 (4)	C13—H13	0.9300
N1—C3	1.345 (3)	C14—H14	0.9300
N1—H1A	0.918 (10)	C15—C16	1.385 (3)
N2—C1	1.367 (3)	C15—H15	0.9300
N3—C11	1.478 (3)	C16—H16	0.9300
N4—C14	1.342 (3)	C17—C18	1.386 (4)
N4—C15	1.344 (3)	C17—C22	1.404 (3)
N4—H4A	0.913 (10)	C18—C19	1.380 (4)
N5—C12	1.365 (3)	C18—H18	0.9300
N6—C22	1.482 (3)	C19—C20	1.379 (4)
C1—C2	1.405 (4)	C19—H19	0.9300
C1—C5	1.419 (4)	C20—C21	1.380 (4)
C2—C3	1.387 (3)	C20—H20	0.9300
C2—H2	0.9300	C21—C22	1.385 (4)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.376 (3)	O9—H9A	0.864 (10)
C4—H4	0.9300	O9—H9B	0.867 (10)
C5—H5	0.9300	O10—H10A	0.867 (10)
C6—C7	1.389 (4)	O10—H10B	0.870 (10)
O2—S1—O1	116.08 (11)	C9—C8—C7	120.3 (3)
O2—S1—N2	114.62 (10)	C9—C8—H8	119.9
O1—S1—N2	106.27 (11)	C7—C8—H8	119.9
O2—S1—C6	105.68 (13)	C10—C9—C8	119.8 (3)
O1—S1—C6	105.03 (11)	C10—C9—H9	120.1
N2—S1—C6	108.55 (13)	C8—C9—H9	120.1
O5—S2—O6	116.29 (11)	C9—C10—C11	119.8 (3)
O5—S2—N5	114.48 (10)	C9—C10—H10	120.1
O6—S2—N5	106.33 (12)	C11—C10—H10	120.1
O5—S2—C17	105.23 (12)	C10—C11—C6	121.9 (3)
O6—S2—C17	105.61 (11)	C10—C11—N3	117.1 (2)
N5—S2—C17	108.33 (12)	C6—C11—N3	121.0 (2)
C4—N1—C3	121.3 (2)	N5—C12—C16	127.0 (2)
C4—N1—H1A	120 (2)	N5—C12—C13	116.4 (2)
C3—N1—H1A	119 (2)	C16—C12—C13	116.6 (2)
C1—N2—S1	123.21 (19)	C14—C13—C12	120.2 (2)
O3—N3—O4	124.9 (3)	C14—C13—H13	119.9
O3—N3—C11	119.3 (2)	C12—C13—H13	119.9
O4—N3—C11	115.9 (2)	N4—C14—C13	121.6 (3)
C14—N4—C15	120.7 (2)	N4—C14—H14	119.2
C14—N4—H4A	118.3 (19)	C13—C14—H14	119.2
C15—N4—H4A	121.0 (19)	N4—C15—C16	120.9 (2)
C12—N5—S2	123.16 (18)	N4—C15—H15	119.6
O7—N6—O8	125.8 (3)	C16—C15—H15	119.6
O7—N6—C22	118.2 (2)	C15—C16—C12	120.0 (2)
O8—N6—C22	115.9 (2)	C15—C16—H16	120.0
N2—C1—C2	116.3 (2)	C12—C16—H16	120.0
N2—C1—C5	127.2 (2)	C18—C17—C22	116.9 (2)
C2—C1—C5	116.5 (2)	C18—C17—S2	119.0 (2)
C3—C2—C1	120.6 (2)	C22—C17—S2	124.1 (2)
C3—C2—H2	119.7	C19—C18—C17	121.1 (2)
C1—C2—H2	119.7	C19—C18—H18	119.4
N1—C3—C2	120.3 (2)	C17—C18—H18	119.4
N1—C3—H3	119.8	C20—C19—C18	121.0 (3)
C2—C3—H3	119.8	C20—C19—H19	119.5
N1—C4—C5	121.1 (3)	C18—C19—H19	119.5
N1—C4—H4	119.5	C19—C20—C21	119.6 (3)
C5—C4—H4	119.5	C19—C20—H20	120.2
C4—C5—C1	120.2 (2)	C21—C20—H20	120.2
C4—C5—H5	119.9	C20—C21—C22	119.1 (3)
C1—C5—H5	119.9	C20—C21—H21	120.4
C7—C6—C11	117.3 (2)	C22—C21—H21	120.4
C7—C6—S1	119.3 (2)	C21—C22—C17	122.3 (2)
C11—C6—S1	123.3 (2)	C21—C22—N6	115.7 (2)
C6—C7—C8	120.9 (3)	C17—C22—N6	122.0 (2)
C6—C7—H7	119.6	H9A—O9—H9B	111.6 (16)
C8—C7—H7	119.6	H10A—O10—H10B	110.7 (16)
O2—S1—N2—C1	36.7 (2)	O4—N3—C11—C10	62.9 (3)
O1—S1—N2—C1	166.3 (2)	O3—N3—C11—C6	64.4 (4)
C6—S1—N2—C1	−81.2 (2)	O4—N3—C11—C6	−116.0 (3)
O5—S2—N5—C12	−36.0 (2)	S2—N5—C12—C16	−4.2 (4)
O6—S2—N5—C12	−165.8 (2)	S2—N5—C12—C13	175.7 (2)
C17—S2—N5—C12	81.0 (2)	N5—C12—C13—C14	−178.5 (2)
S1—N2—C1—C2	−178.07 (19)	C16—C12—C13—C14	1.4 (4)
S1—N2—C1—C5	1.5 (4)	C15—N4—C14—C13	−0.6 (4)
N2—C1—C2—C3	177.8 (2)	C12—C13—C14—N4	−0.4 (4)
C5—C1—C2—C3	−1.9 (4)	C14—N4—C15—C16	0.6 (4)
C4—N1—C3—C2	−0.8 (4)	N4—C15—C16—C12	0.4 (4)
C1—C2—C3—N1	1.4 (4)	N5—C12—C16—C15	178.5 (2)
C3—N1—C4—C5	0.7 (4)	C13—C12—C16—C15	−1.3 (4)
N1—C4—C5—C1	−1.2 (4)	O5—S2—C17—C18	18.6 (2)
N2—C1—C5—C4	−177.8 (3)	O6—S2—C17—C18	142.2 (2)
C2—C1—C5—C4	1.8 (4)	N5—S2—C17—C18	−104.2 (2)
O2—S1—C6—C7	−14.8 (2)	O5—S2—C17—C22	−159.0 (2)
O1—S1—C6—C7	−138.0 (2)	O6—S2—C17—C22	−35.5 (3)
N2—S1—C6—C7	108.6 (2)	N5—S2—C17—C22	78.1 (2)
O2—S1—C6—C11	161.6 (2)	C22—C17—C18—C19	−1.0 (4)
O1—S1—C6—C11	38.3 (3)	S2—C17—C18—C19	−178.8 (2)
N2—S1—C6—C11	−75.0 (2)	C17—C18—C19—C20	1.1 (4)
C11—C6—C7—C8	0.6 (4)	C18—C19—C20—C21	0.1 (4)
S1—C6—C7—C8	177.2 (2)	C19—C20—C21—C22	−1.2 (4)
C6—C7—C8—C9	−0.1 (4)	C20—C21—C22—C17	1.3 (4)
C7—C8—C9—C10	−1.1 (4)	C20—C21—C22—N6	−179.0 (2)
C8—C9—C10—C11	1.7 (4)	C18—C17—C22—C21	−0.2 (4)
C9—C10—C11—C6	−1.2 (4)	S2—C17—C22—C21	177.5 (2)
C9—C10—C11—N3	180.0 (2)	C18—C17—C22—N6	−179.9 (2)
C7—C6—C11—C10	0.0 (4)	S2—C17—C22—N6	−2.2 (4)
S1—C6—C11—C10	−176.4 (2)	O7—N6—C22—C21	116.6 (3)
C7—C6—C11—N3	178.8 (2)	O8—N6—C22—C21	−62.4 (3)
S1—C6—C11—N3	2.4 (4)	O7—N6—C22—C17	−63.7 (4)
O3—N3—C11—C10	−116.7 (3)	O8—N6—C22—C17	117.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O9	0.913 (10)	1.868 (12)	2.764 (3)	167 (3)
O9—H9A···O1	0.864 (10)	2.122 (11)	2.967 (3)	166 (3)
N1—H1A···O10i	0.918 (10)	1.843 (11)	2.757 (3)	174 (4)
O9—H9B···N5ii	0.867 (10)	2.043 (11)	2.901 (3)	170 (2)
O9—H9B···O6ii	0.867 (10)	2.56 (2)	3.125 (3)	123 (2)
O10—H10A···O6iii	0.867 (10)	2.051 (11)	2.914 (3)	174 (4)
O10—H10B···N2iv	0.870 (10)	2.042 (12)	2.902 (3)	170 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O9	0.913 (10)	1.868 (12)	2.764 (3)	167 (3)
O9—H9A⋯O1	0.864 (10)	2.122 (11)	2.967 (3)	166 (3)
N1—H1A⋯O10i	0.918 (10)	1.843 (11)	2.757 (3)	174 (4)
O9—H9B⋯N5ii	0.867 (10)	2.043 (11)	2.901 (3)	170 (2)
O9—H9B⋯O6ii	0.867 (10)	2.56 (2)	3.125 (3)	123 (2)
O10—H10A⋯O6iii	0.867 (10)	2.051 (11)	2.914 (3)	174 (4)
O10—H10B⋯N2iv	0.870 (10)	2.042 (12)	2.902 (3)	170 (3)

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