tert-But-yl(2-hy-droxy-eth-yl)aza-nium 4-[(1,3-thia-zol-2-yl-aza-nid-yl)sulfon-yl]aniline.

Two pairs of independent cations and anions comprise the asymmetric unit of the title salt, C(6)H(16)NO(+)·C(9)H(8)N(3)O(2)S(2) (-). The cations are virtually superimposable and each exhibits a gauche disposition of the hy-droxy O and ammonium N atoms [the O-C-C-N torsion angles are 55.5 (3) and 57.5 (3)°]. Significant differences are seen in the mol-ecular structures of the anions as seen in the S-N-C-S [1.1 (3) and 32.9 (3)°] and C-S-N-C [-69.7 (2) and 91.4 (2)°] torsion angles. Despite the variations in conformation, intra-molecular hypervalent S⋯O inter-actions persist in each anion [3.078 (2) and 2.8730 (19) Å]. In the crystal, supra-molecular double layers are formed in the bc plane, being sustained by O-H⋯N, N-H⋯O and N-H⋯N hydrogen bonding. These are connected along the a axis via C-H⋯O inter-actions.

Related literature

For structural studies of sulfathia­zole and derivatives, see: Bingham et al. (2001 ▶); Caira (2007 ▶). For previous crystal engineering studies, see: Arman, Kaulgud, Miller, Poplaukhin et al. (2012 ▶); Arman, Kaulgud, Miller & Tiekink (2012 ▶). For hypervalent S⋯O inter­actions, see: O’Leary & Wallis (2007 ▶). For the structure of a related aza­nide, see: Brennan et al. (1971 ▶).

Experimental

Crystal data

C6H16NO+·C9H8N3O2S2 −

M = 372.50

Monoclinic,

a = 13.893 (3) Å

b = 11.771 (3) Å

c = 22.191 (5) Å

β = 91.401 (4)°

V = 3627.9 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.32 mm−1

T = 98 K

0.35 × 0.30 × 0.07 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer

18273 measured reflections

8255 independent reflections

7234 reflections with I > 2σ(I)

R int = 0.056

Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.136

S = 1.08

8255 reflections

451 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 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: ORTEP-3 for Windows (Farrugia, 1997 ▶), DIAMOND (Brandenburg, 2006 ▶) and QMol (Gans & Shalloway, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034459/bt5992sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034459/bt5992Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034459/bt5992Isup3.cml

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

C6H16NO+·C9H8N3O2S2−	F(000) = 1584
Mr = 372.50	Dx = 1.364 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 24162 reflections
a = 13.893 (3) Å	θ = 2.4–40.3°
b = 11.771 (3) Å	µ = 0.32 mm−1
c = 22.191 (5) Å	T = 98 K
β = 91.401 (4)°	Plate, colourless
V = 3627.9 (15) Å3	0.35 × 0.30 × 0.07 mm
Z = 8

Rigaku AFC12K/SATURN724 diffractometer	7234 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.056
Graphite monochromator	θmax = 27.5°, θmin = 2.4°
ω scans	h = −17→18
18273 measured reflections	k = −15→5
8255 independent reflections	l = −23→28

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0435P)2 + 3.8739P] where P = (Fo2 + 2Fc2)/3
8255 reflections	(Δ/σ)max = 0.001
451 parameters	Δρmax = 0.36 e Å−3
8 restraints	Δρmin = −0.45 e Å−3

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 > 2σ(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	0.16821 (5)	0.10093 (5)	0.47147 (3)	0.02469 (14)
S2	0.36615 (4)	0.23512 (5)	0.50339 (3)	0.01958 (13)
O1	0.38569 (13)	0.11406 (15)	0.50058 (8)	0.0254 (4)
O2	0.45054 (12)	0.30808 (16)	0.50206 (8)	0.0243 (4)
N1	0.15549 (15)	0.26042 (19)	0.39238 (10)	0.0236 (4)
N2	0.29650 (14)	0.27894 (17)	0.45040 (9)	0.0192 (4)
N3	0.16937 (17)	0.3130 (2)	0.73461 (10)	0.0282 (5)
H1n	0.174 (2)	0.261 (2)	0.7627 (11)	0.042*
H2n	0.153 (2)	0.3833 (12)	0.7421 (14)	0.042*
C1	0.21311 (17)	0.2228 (2)	0.43601 (11)	0.0196 (5)
C2	0.07372 (18)	0.1937 (2)	0.38592 (12)	0.0261 (5)
H2	0.0251	0.2092	0.3562	0.031*
C3	0.06738 (19)	0.1054 (2)	0.42428 (12)	0.0269 (5)
H3	0.0152	0.0533	0.4252	0.032*
C4	0.30798 (17)	0.2583 (2)	0.57212 (10)	0.0187 (4)
C5	0.26187 (17)	0.3620 (2)	0.58306 (11)	0.0203 (5)
H5	0.2614	0.4196	0.5531	0.024*
C6	0.21712 (17)	0.3812 (2)	0.63700 (11)	0.0211 (5)
H6	0.1866	0.4520	0.6441	0.025*
C7	0.21672 (17)	0.2954 (2)	0.68182 (11)	0.0221 (5)
C8	0.26184 (18)	0.1920 (2)	0.67037 (11)	0.0236 (5)
H8	0.2615	0.1336	0.6999	0.028*
C9	0.30725 (18)	0.1737 (2)	0.61606 (11)	0.0221 (5)
H9	0.3380	0.1030	0.6088	0.027*
S11	0.28142 (5)	0.98598 (5)	0.32531 (3)	0.02459 (14)
S12	0.14994 (4)	0.80923 (5)	0.23655 (3)	0.01828 (13)
O11	0.06213 (12)	0.74301 (16)	0.23845 (8)	0.0230 (4)
O12	0.13976 (12)	0.93223 (15)	0.23321 (8)	0.0224 (4)
N11	0.35743 (15)	0.79060 (18)	0.34885 (9)	0.0222 (4)
N12	0.21478 (14)	0.76971 (17)	0.29279 (9)	0.0197 (4)
N13	0.37494 (17)	0.6429 (2)	0.02991 (11)	0.0298 (5)
H11n	0.4289 (15)	0.676 (2)	0.0189 (15)	0.045*
H12n	0.364 (2)	0.5731 (14)	0.0170 (15)	0.045*
C11	0.28445 (16)	0.8372 (2)	0.31912 (10)	0.0174 (4)
C12	0.41351 (18)	0.8728 (2)	0.37772 (11)	0.0235 (5)
H12	0.4690	0.8536	0.4015	0.028*
C13	0.38494 (19)	0.9815 (2)	0.37019 (11)	0.0258 (5)
H13	0.4169	1.0459	0.3870	0.031*
C14	0.21076 (17)	0.7648 (2)	0.17170 (10)	0.0189 (4)
C15	0.28885 (17)	0.8281 (2)	0.15081 (11)	0.0214 (5)
H15	0.3047	0.8988	0.1691	0.026*
C16	0.34297 (18)	0.7878 (2)	0.10361 (11)	0.0223 (5)
H16	0.3954	0.8316	0.0897	0.027*
C17	0.32109 (17)	0.6825 (2)	0.07608 (11)	0.0212 (5)
C18	0.24137 (17)	0.6213 (2)	0.09704 (11)	0.0213 (5)
H18	0.2243	0.5511	0.0785	0.026*
C19	0.18755 (17)	0.6616 (2)	0.14420 (11)	0.0206 (5)
H19	0.1345	0.6186	0.1579	0.025*
O21	0.20607 (12)	0.43422 (15)	0.31746 (8)	0.0221 (4)
H21o	0.190 (2)	0.383 (2)	0.3413 (12)	0.033*
N21	0.12174 (14)	0.62867 (17)	0.37680 (9)	0.0190 (4)
H21n	0.1508	0.6739	0.3487	0.023*
H22n	0.1699	0.5903	0.3974	0.023*
C21	0.11863 (18)	0.4853 (2)	0.29455 (11)	0.0220 (5)
H21A	0.0783	0.4260	0.2748	0.026*
H21B	0.1347	0.5423	0.2636	0.026*
C22	0.06114 (17)	0.5426 (2)	0.34340 (11)	0.0228 (5)
H22A	0.0041	0.5805	0.3249	0.027*
H22B	0.0383	0.4846	0.3720	0.027*
C23	0.07187 (17)	0.7065 (2)	0.42153 (11)	0.0203 (5)
C24	0.15194 (18)	0.7693 (2)	0.45610 (12)	0.0257 (5)
H24A	0.1885	0.8158	0.4280	0.039*
H24B	0.1951	0.7141	0.4758	0.039*
H24C	0.1236	0.8185	0.4866	0.039*
C25	0.00759 (19)	0.7910 (2)	0.38651 (12)	0.0268 (5)
H25A	0.0471	0.8361	0.3595	0.040*
H25B	−0.0243	0.8415	0.4149	0.040*
H25C	−0.0412	0.7492	0.3628	0.040*
C26	0.0141 (2)	0.6337 (2)	0.46453 (12)	0.0293 (6)
H26A	−0.0371	0.5939	0.4418	0.044*
H26B	−0.0146	0.6824	0.4951	0.044*
H26C	0.0568	0.5780	0.4843	0.044*
O31	0.26830 (12)	0.51401 (15)	0.44630 (8)	0.0220 (4)
H31o	0.275 (2)	0.4438 (9)	0.4450 (14)	0.033*
N31	0.38695 (14)	0.55543 (17)	0.34314 (9)	0.0184 (4)
H31n	0.3735	0.6319	0.3438	0.022*
H32n	0.3293	0.5178	0.3378	0.022*
C31	0.36309 (17)	0.5610 (2)	0.45343 (11)	0.0224 (5)
H31A	0.3912	0.5372	0.4929	0.027*
H31B	0.3588	0.6450	0.4533	0.027*
C32	0.42873 (17)	0.5231 (2)	0.40364 (11)	0.0220 (5)
H32A	0.4928	0.5589	0.4094	0.026*
H32B	0.4373	0.4396	0.4056	0.026*
C33	0.44814 (17)	0.5317 (2)	0.28840 (11)	0.0209 (5)
C34	0.46354 (19)	0.4039 (2)	0.28245 (12)	0.0271 (5)
H34A	0.5006	0.3761	0.3176	0.041*
H34B	0.4989	0.3881	0.2457	0.041*
H34C	0.4010	0.3655	0.2803	0.041*
C35	0.54298 (18)	0.5966 (2)	0.29574 (12)	0.0282 (6)
H35A	0.5796	0.5666	0.3306	0.042*
H35B	0.5295	0.6774	0.3021	0.042*
H35C	0.5807	0.5873	0.2593	0.042*
C36	0.39072 (18)	0.5777 (2)	0.23432 (11)	0.0241 (5)
H36A	0.3817	0.6598	0.2390	0.036*
H36B	0.3277	0.5402	0.2319	0.036*
H36C	0.4258	0.5626	0.1974	0.036*

	U11	U22	U33	U12	U13	U23
S1	0.0275 (3)	0.0196 (3)	0.0267 (3)	−0.0048 (2)	−0.0058 (2)	0.0056 (2)
S2	0.0187 (3)	0.0186 (3)	0.0213 (3)	0.0015 (2)	−0.0034 (2)	−0.0021 (2)
O1	0.0311 (10)	0.0188 (9)	0.0260 (9)	0.0069 (7)	−0.0054 (7)	−0.0034 (7)
O2	0.0177 (8)	0.0286 (10)	0.0264 (9)	−0.0019 (7)	−0.0026 (7)	−0.0046 (7)
N1	0.0230 (10)	0.0228 (11)	0.0246 (11)	−0.0042 (8)	−0.0055 (8)	0.0027 (8)
N2	0.0202 (10)	0.0170 (10)	0.0203 (10)	−0.0020 (7)	−0.0037 (7)	−0.0004 (8)
N3	0.0342 (12)	0.0267 (12)	0.0240 (11)	−0.0049 (9)	0.0045 (9)	0.0014 (9)
C1	0.0225 (11)	0.0168 (11)	0.0195 (11)	0.0015 (9)	−0.0010 (9)	−0.0024 (9)
C2	0.0233 (12)	0.0278 (13)	0.0267 (13)	−0.0049 (10)	−0.0076 (10)	0.0011 (10)
C3	0.0265 (13)	0.0254 (13)	0.0285 (13)	−0.0077 (10)	−0.0048 (10)	0.0020 (10)
C4	0.0204 (11)	0.0187 (11)	0.0169 (11)	0.0009 (8)	−0.0015 (8)	−0.0024 (9)
C5	0.0212 (11)	0.0168 (11)	0.0229 (11)	0.0000 (9)	−0.0021 (9)	0.0017 (9)
C6	0.0208 (11)	0.0176 (11)	0.0247 (12)	−0.0008 (8)	−0.0030 (9)	−0.0018 (9)
C7	0.0177 (11)	0.0250 (13)	0.0232 (12)	−0.0065 (9)	−0.0032 (9)	−0.0002 (10)
C8	0.0254 (12)	0.0201 (12)	0.0249 (12)	−0.0040 (9)	−0.0061 (9)	0.0060 (10)
C9	0.0255 (12)	0.0159 (11)	0.0247 (12)	−0.0005 (9)	−0.0047 (9)	0.0009 (9)
S11	0.0278 (3)	0.0170 (3)	0.0287 (3)	−0.0006 (2)	−0.0042 (2)	−0.0020 (2)
S12	0.0177 (3)	0.0187 (3)	0.0183 (3)	−0.0004 (2)	−0.0012 (2)	0.0003 (2)
O11	0.0186 (8)	0.0276 (10)	0.0228 (9)	−0.0041 (7)	−0.0007 (6)	−0.0013 (7)
O12	0.0260 (9)	0.0192 (9)	0.0220 (8)	0.0040 (7)	−0.0008 (7)	0.0012 (7)
N11	0.0226 (10)	0.0219 (11)	0.0218 (10)	0.0010 (8)	−0.0029 (8)	−0.0012 (8)
N12	0.0224 (10)	0.0185 (10)	0.0181 (10)	−0.0026 (8)	−0.0026 (7)	0.0039 (8)
N13	0.0309 (12)	0.0275 (12)	0.0313 (12)	−0.0018 (9)	0.0072 (9)	−0.0037 (10)
C11	0.0197 (11)	0.0170 (11)	0.0155 (10)	−0.0012 (8)	0.0030 (8)	−0.0012 (8)
C12	0.0229 (12)	0.0264 (13)	0.0209 (12)	−0.0037 (9)	−0.0033 (9)	−0.0032 (10)
C13	0.0277 (13)	0.0265 (13)	0.0230 (12)	−0.0072 (10)	−0.0016 (10)	−0.0036 (10)
C14	0.0195 (11)	0.0185 (11)	0.0186 (11)	0.0014 (8)	−0.0014 (8)	0.0008 (9)
C15	0.0219 (11)	0.0178 (11)	0.0243 (12)	−0.0006 (9)	−0.0015 (9)	0.0002 (9)
C16	0.0233 (12)	0.0203 (12)	0.0234 (12)	−0.0034 (9)	0.0005 (9)	0.0023 (9)
C17	0.0186 (11)	0.0237 (12)	0.0211 (11)	0.0022 (9)	−0.0048 (9)	0.0032 (9)
C18	0.0241 (12)	0.0174 (11)	0.0222 (12)	−0.0009 (9)	−0.0044 (9)	0.0002 (9)
C19	0.0175 (11)	0.0223 (12)	0.0218 (11)	−0.0023 (8)	−0.0024 (9)	0.0038 (9)
O21	0.0238 (9)	0.0189 (9)	0.0236 (9)	−0.0015 (7)	−0.0022 (7)	0.0033 (7)
N21	0.0178 (9)	0.0182 (10)	0.0210 (10)	−0.0027 (7)	−0.0010 (7)	0.0016 (8)
C21	0.0269 (12)	0.0177 (11)	0.0214 (12)	−0.0006 (9)	−0.0047 (9)	−0.0017 (9)
C22	0.0219 (12)	0.0192 (12)	0.0270 (12)	−0.0031 (9)	−0.0023 (9)	−0.0028 (10)
C23	0.0209 (11)	0.0193 (12)	0.0208 (11)	0.0002 (9)	0.0025 (9)	−0.0019 (9)
C24	0.0244 (12)	0.0269 (13)	0.0258 (13)	−0.0027 (10)	−0.0007 (10)	−0.0057 (10)
C25	0.0259 (13)	0.0216 (13)	0.0328 (14)	0.0023 (10)	−0.0010 (10)	−0.0025 (10)
C26	0.0326 (14)	0.0291 (14)	0.0265 (13)	−0.0055 (11)	0.0082 (10)	0.0018 (11)
O31	0.0227 (8)	0.0190 (9)	0.0242 (9)	−0.0016 (7)	−0.0032 (7)	−0.0003 (7)
N31	0.0188 (9)	0.0166 (10)	0.0197 (10)	−0.0011 (7)	−0.0034 (7)	0.0017 (7)
C31	0.0240 (12)	0.0225 (12)	0.0206 (11)	−0.0016 (9)	−0.0036 (9)	−0.0005 (9)
C32	0.0225 (12)	0.0228 (12)	0.0204 (12)	0.0020 (9)	−0.0050 (9)	0.0014 (9)
C33	0.0215 (11)	0.0219 (12)	0.0193 (11)	0.0009 (9)	−0.0013 (9)	−0.0003 (9)
C34	0.0296 (13)	0.0243 (13)	0.0270 (13)	0.0062 (10)	−0.0056 (10)	−0.0019 (10)
C35	0.0208 (12)	0.0343 (15)	0.0294 (13)	−0.0041 (10)	0.0007 (10)	−0.0043 (11)
C36	0.0256 (12)	0.0260 (13)	0.0206 (12)	0.0030 (10)	−0.0009 (9)	0.0019 (10)

S1—C3	1.729 (3)	C18—H18	0.9500
S1—C1	1.758 (3)	C19—H19	0.9500
S2—O1	1.4524 (18)	O21—C21	1.437 (3)
S2—O2	1.4542 (18)	O21—H21O	0.835 (10)
S2—N2	1.590 (2)	N21—C22	1.502 (3)
S2—C4	1.765 (2)	N21—C23	1.529 (3)
N1—C1	1.318 (3)	N21—H21N	0.9200
N1—C2	1.386 (3)	N21—H22N	0.9200
N2—C1	1.365 (3)	C21—C22	1.520 (3)
N3—C7	1.373 (3)	C21—H21A	0.9900
N3—H1N	0.873 (10)	C21—H21B	0.9900
N3—H2N	0.875 (10)	C22—H22A	0.9900
C2—C3	1.348 (4)	C22—H22B	0.9900
C2—H2	0.9500	C23—C26	1.526 (3)
C3—H3	0.9500	C23—C24	1.527 (3)
C4—C9	1.394 (3)	C23—C25	1.535 (3)
C4—C5	1.402 (3)	C24—H24A	0.9800
C5—C6	1.381 (3)	C24—H24B	0.9800
C5—H5	0.9500	C24—H24C	0.9800
C6—C7	1.417 (3)	C25—H25A	0.9800
C6—H6	0.9500	C25—H25B	0.9800
C7—C8	1.395 (4)	C25—H25C	0.9800
C8—C9	1.391 (4)	C26—H26A	0.9800
C8—H8	0.9500	C26—H26B	0.9800
C9—H9	0.9500	C26—H26C	0.9800
S11—C13	1.730 (3)	O31—C31	1.434 (3)
S11—C11	1.757 (2)	O31—H31O	0.833 (10)
S12—O11	1.4493 (17)	N31—C32	1.499 (3)
S12—O12	1.4563 (18)	N31—C33	1.525 (3)
S12—N12	1.591 (2)	N31—H31N	0.9200
S12—C14	1.766 (2)	N31—H32N	0.9200
N11—C11	1.316 (3)	C31—C32	1.517 (3)
N11—C12	1.389 (3)	C31—H31A	0.9900
N12—C11	1.372 (3)	C31—H31B	0.9900
N13—C17	1.365 (3)	C32—H32A	0.9900
N13—H11N	0.882 (10)	C32—H32B	0.9900
N13—H12N	0.882 (10)	C33—C36	1.524 (3)
C12—C13	1.348 (4)	C33—C34	1.525 (3)
C12—H12	0.9500	C33—C35	1.528 (3)
C13—H13	0.9500	C34—H34A	0.9800
C14—C19	1.394 (3)	C34—H34B	0.9800
C14—C15	1.404 (3)	C34—H34C	0.9800
C15—C16	1.388 (3)	C35—H35A	0.9800
C15—H15	0.9500	C35—H35B	0.9800
C16—C17	1.412 (4)	C35—H35C	0.9800
C16—H16	0.9500	C36—H36A	0.9800
C17—C18	1.410 (3)	C36—H36B	0.9800
C18—C19	1.385 (3)	C36—H36C	0.9800
C3—S1—C1	89.73 (12)	C22—N21—H22N	107.8
O1—S2—O2	115.27 (11)	C23—N21—H22N	107.8
O1—S2—N2	113.42 (11)	H21N—N21—H22N	107.2
O2—S2—N2	105.65 (11)	O21—C21—C22	112.8 (2)
O1—S2—C4	106.20 (11)	O21—C21—H21A	109.0
O2—S2—C4	108.22 (11)	C22—C21—H21A	109.0
N2—S2—C4	107.80 (11)	O21—C21—H21B	109.0
C1—N1—C2	111.5 (2)	C22—C21—H21B	109.0
C1—N2—S2	120.90 (17)	H21A—C21—H21B	107.8
C7—N3—H1N	118 (2)	N21—C22—C21	110.69 (19)
C7—N3—H2N	116 (2)	N21—C22—H22A	109.5
H1N—N3—H2N	123 (2)	C21—C22—H22A	109.5
N1—C1—N2	120.4 (2)	N21—C22—H22B	109.5
N1—C1—S1	112.79 (18)	C21—C22—H22B	109.5
N2—C1—S1	126.79 (18)	H22A—C22—H22B	108.1
C3—C2—N1	116.0 (2)	C26—C23—C24	110.2 (2)
C3—C2—H2	122.0	C26—C23—N21	108.8 (2)
N1—C2—H2	122.0	C24—C23—N21	106.28 (19)
C2—C3—S1	109.96 (19)	C26—C23—C25	111.8 (2)
C2—C3—H3	125.0	C24—C23—C25	110.4 (2)
S1—C3—H3	125.0	N21—C23—C25	109.06 (19)
C9—C4—C5	119.3 (2)	C23—C24—H24A	109.5
C9—C4—S2	120.35 (18)	C23—C24—H24B	109.5
C5—C4—S2	120.34 (18)	H24A—C24—H24B	109.5
C6—C5—C4	120.7 (2)	C23—C24—H24C	109.5
C6—C5—H5	119.7	H24A—C24—H24C	109.5
C4—C5—H5	119.7	H24B—C24—H24C	109.5
C5—C6—C7	120.1 (2)	C23—C25—H25A	109.5
C5—C6—H6	120.0	C23—C25—H25B	109.5
C7—C6—H6	120.0	H25A—C25—H25B	109.5
N3—C7—C8	120.9 (2)	C23—C25—H25C	109.5
N3—C7—C6	120.1 (2)	H25A—C25—H25C	109.5
C8—C7—C6	119.0 (2)	H25B—C25—H25C	109.5
C9—C8—C7	120.6 (2)	C23—C26—H26A	109.5
C9—C8—H8	119.7	C23—C26—H26B	109.5
C7—C8—H8	119.7	H26A—C26—H26B	109.5
C8—C9—C4	120.4 (2)	C23—C26—H26C	109.5
C8—C9—H9	119.8	H26A—C26—H26C	109.5
C4—C9—H9	119.8	H26B—C26—H26C	109.5
C13—S11—C11	89.62 (12)	C31—O31—H31O	106 (2)
O11—S12—O12	117.09 (11)	C32—N31—C33	117.09 (18)
O11—S12—N12	106.30 (11)	C32—N31—H31N	108.0
O12—S12—N12	112.52 (11)	C33—N31—H31N	108.0
O11—S12—C14	106.52 (11)	C32—N31—H32N	108.0
O12—S12—C14	107.51 (11)	C33—N31—H32N	108.0
N12—S12—C14	106.24 (11)	H31N—N31—H32N	107.3
C11—N11—C12	110.9 (2)	O31—C31—C32	111.9 (2)
C11—N12—S12	123.00 (17)	O31—C31—H31A	109.2
C17—N13—H11N	123 (2)	C32—C31—H31A	109.2
C17—N13—H12N	118 (2)	O31—C31—H31B	109.2
H11N—N13—H12N	117 (2)	C32—C31—H31B	109.2
N11—C11—N12	119.9 (2)	H31A—C31—H31B	107.9
N11—C11—S11	113.34 (18)	N31—C32—C31	110.55 (19)
N12—C11—S11	126.35 (18)	N31—C32—H32A	109.5
C13—C12—N11	116.3 (2)	C31—C32—H32A	109.5
C13—C12—H12	121.8	N31—C32—H32B	109.5
N11—C12—H12	121.8	C31—C32—H32B	109.5
C12—C13—S11	109.79 (19)	H32A—C32—H32B	108.1
C12—C13—H13	125.1	C36—C33—C34	110.7 (2)
S11—C13—H13	125.1	C36—C33—N31	105.70 (19)
C19—C14—C15	119.4 (2)	C34—C33—N31	109.4 (2)
C19—C14—S12	120.32 (18)	C36—C33—C35	109.8 (2)
C15—C14—S12	120.05 (19)	C34—C33—C35	112.3 (2)
C16—C15—C14	120.3 (2)	N31—C33—C35	108.62 (19)
C16—C15—H15	119.8	C33—C34—H34A	109.5
C14—C15—H15	119.8	C33—C34—H34B	109.5
C15—C16—C17	120.8 (2)	H34A—C34—H34B	109.5
C15—C16—H16	119.6	C33—C34—H34C	109.5
C17—C16—H16	119.6	H34A—C34—H34C	109.5
N13—C17—C18	121.5 (2)	H34B—C34—H34C	109.5
N13—C17—C16	120.6 (2)	C33—C35—H35A	109.5
C18—C17—C16	118.0 (2)	C33—C35—H35B	109.5
C19—C18—C17	121.1 (2)	H35A—C35—H35B	109.5
C19—C18—H18	119.4	C33—C35—H35C	109.5
C17—C18—H18	119.4	H35A—C35—H35C	109.5
C18—C19—C14	120.4 (2)	H35B—C35—H35C	109.5
C18—C19—H19	119.8	C33—C36—H36A	109.5
C14—C19—H19	119.8	C33—C36—H36B	109.5
C21—O21—H21O	107 (2)	H36A—C36—H36B	109.5
C22—N21—C23	117.87 (18)	C33—C36—H36C	109.5
C22—N21—H21N	107.8	H36A—C36—H36C	109.5
C23—N21—H21N	107.8	H36B—C36—H36C	109.5
O1—S2—N2—C1	47.6 (2)	S12—N12—C11—N11	−154.89 (18)
O2—S2—N2—C1	174.80 (18)	S12—N12—C11—S11	32.9 (3)
C4—S2—N2—C1	−69.7 (2)	C13—S11—C11—N11	0.25 (19)
C2—N1—C1—N2	−178.3 (2)	C13—S11—C11—N12	172.9 (2)
C2—N1—C1—S1	0.2 (3)	C11—N11—C12—C13	−0.4 (3)
S2—N2—C1—N1	179.38 (19)	N11—C12—C13—S11	0.6 (3)
S2—N2—C1—S1	1.1 (3)	C11—S11—C13—C12	−0.5 (2)
C3—S1—C1—N1	−0.5 (2)	O11—S12—C14—C19	−18.3 (2)
C3—S1—C1—N2	177.9 (2)	O12—S12—C14—C19	−144.61 (19)
C1—N1—C2—C3	0.3 (3)	N12—S12—C14—C19	94.7 (2)
N1—C2—C3—S1	−0.7 (3)	O11—S12—C14—C15	167.58 (19)
C1—S1—C3—C2	0.6 (2)	O12—S12—C14—C15	41.3 (2)
O1—S2—C4—C9	13.0 (2)	N12—S12—C14—C15	−79.4 (2)
O2—S2—C4—C9	−111.3 (2)	C19—C14—C15—C16	−0.6 (4)
N2—S2—C4—C9	134.9 (2)	S12—C14—C15—C16	173.55 (19)
O1—S2—C4—C5	−166.88 (19)	C14—C15—C16—C17	−0.5 (4)
O2—S2—C4—C5	68.8 (2)	C15—C16—C17—N13	−179.6 (2)
N2—S2—C4—C5	−45.0 (2)	C15—C16—C17—C18	1.5 (4)
C9—C4—C5—C6	0.8 (4)	N13—C17—C18—C19	179.5 (2)
S2—C4—C5—C6	−179.28 (18)	C16—C17—C18—C19	−1.6 (4)
C4—C5—C6—C7	−0.5 (4)	C17—C18—C19—C14	0.6 (4)
C5—C6—C7—N3	−177.7 (2)	C15—C14—C19—C18	0.5 (4)
C5—C6—C7—C8	−0.2 (3)	S12—C14—C19—C18	−173.60 (18)
N3—C7—C8—C9	178.1 (2)	C23—N21—C22—C21	171.49 (19)
C6—C7—C8—C9	0.6 (4)	O21—C21—C22—N21	55.5 (3)
C7—C8—C9—C4	−0.3 (4)	C22—N21—C23—C26	51.7 (3)
C5—C4—C9—C8	−0.4 (4)	C22—N21—C23—C24	170.4 (2)
S2—C4—C9—C8	179.69 (19)	C22—N21—C23—C25	−70.6 (3)
O11—S12—N12—C11	−155.40 (19)	C33—N31—C32—C31	175.3 (2)
O12—S12—N12—C11	−26.0 (2)	O31—C31—C32—N31	57.5 (3)
C14—S12—N12—C11	91.4 (2)	C32—N31—C33—C36	−177.4 (2)
C12—N11—C11—N12	−173.1 (2)	C32—N31—C33—C34	63.4 (3)
C12—N11—C11—S11	0.0 (3)	C32—N31—C33—C35	−59.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O21—H21o···N1	0.84 (3)	1.90 (3)	2.739 (3)	177 (2)
O31—H31o···N2	0.83 (1)	1.97 (1)	2.796 (3)	174 (3)
N3—H2n···O12i	0.88 (2)	2.19 (2)	3.027 (3)	161 (3)
N13—H11n···O2ii	0.89 (2)	2.34 (2)	3.201 (3)	164 (2)
N13—H12n···O1iii	0.88 (2)	2.25 (2)	3.098 (3)	160 (2)
N21—H21n···N12	0.92	1.91	2.832 (3)	178
N21—H22n···O31	0.92	1.94	2.862 (3)	176
N31—H31n···N11	0.92	1.89	2.802 (3)	175
N31—H32n···O21	0.92	2.02	2.934 (3)	174
C2—H2···O11iv	0.95	2.43	3.356 (3)	164
C6—H6···O12i	0.95	2.50	3.263 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O21—H21o⋯N1	0.84 (3)	1.90 (3)	2.739 (3)	177 (2)
O31—H31o⋯N2	0.83 (1)	1.97 (1)	2.796 (3)	174 (3)
N3—H2n⋯O12i	0.88 (2)	2.19 (2)	3.027 (3)	161 (3)
N13—H11n⋯O2ii	0.89 (2)	2.34 (2)	3.201 (3)	164 (2)
N13—H12n⋯O1iii	0.88 (2)	2.25 (2)	3.098 (3)	160 (2)
N21—H21n⋯N12	0.92	1.91	2.832 (3)	178
N21—H22n⋯O31	0.92	1.94	2.862 (3)	176
N31—H31n⋯N11	0.92	1.89	2.802 (3)	175
N31—H32n⋯O21	0.92	2.02	2.934 (3)	174
C2—H2⋯O11iv	0.95	2.43	3.356 (3)	164
C6—H6⋯O12i	0.95	2.50	3.263 (3)	137

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