4-Benzyl-3-(2-fur-yl)-1H-1,2,4-triazole-5(4H)-thione hemihydrate.

In the asymmetric unit of the title compound, C(13)H(11)N(3)OS·0.5H(2)O, there are two independent mol-ecules of 4-benzyl-3-(2-fur-yl)-1H-1,2,4-triazole-5(4H)-thione and a water mol-ecule of hydration. The conformation of the two organic mol-ecules is slightly different, the dihedral angles formed by the furyl and triazole rings being 5.63 (15) and 17.66 (13)°. The water mol-ecule of hydration links three adjacent triazole mol-ecules to form a cluster via inter-molecular O-H⋯S, N-H⋯S and N-H⋯O hydrogen bonds, generating a 10-membered ring of graph set R(3) (3)(10). The crystal structure is further stabilized by intra- and inter-molecular C-H⋯S, C-H⋯O and C-H⋯N hydrogen bonds and by π-π stacking inter-actions involving the furyl and triazole rings of centrosymmetrically related mol-ecules, with a centroid-centroid separation of 3.470 (2) Å.

Related literature

For related literature, see: Ahmad et al. (2001 ▶); Altman & Solomost (1993 ▶); Chai et al. (2003 ▶); Dege et al. (2004 ▶); Hashimoto et al. (1990 ▶); Kanazawa et al. (1988 ▶); Öztürk et al. (2004 ▶); Yıldırım et al. (2004 ▶); Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C13H11N3OS·0.5H2O

M = 266.33

Triclinic,

a = 6.082 (2) Å

b = 12.069 (4) Å

c = 17.818 (5) Å

α = 92.43 (2)°

β = 94.35 (2)°

γ = 103.83 (2)°

V = 1263.9 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 173 (2) K

0.18 × 0.16 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.956, T max = 0.990

10729 measured reflections

5735 independent reflections

4365 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.096

S = 1.03

5735 reflections

347 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.24 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); 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 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012361/rz2207sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012361/rz2207Isup2.hkl

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

C13H11N3OS·0.5H2O	Z = 4
Mr = 266.33	F000 = 556
Triclinic, P1	Dx = 1.400 Mg m−3
Hall symbol: -P 1	Melting point = 458–459 K
a = 6.082 (2) Å	Mo Kα radiation λ = 0.71073 Å
b = 12.069 (4) Å	Cell parameters from 10729 reflections
c = 17.818 (5) Å	θ = 3.0–27.5º
α = 92.43 (2)º	µ = 0.25 mm−1
β = 94.35 (2)º	T = 173 (2) K
γ = 103.83 (2)º	Plate, colourless
V = 1263.9 (7) Å3	0.18 × 0.16 × 0.04 mm

Nonius KappaCCD diffractometer	5735 independent reflections
Radiation source: fine-focus sealed tube	4365 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
T = 173(2) K	θmax = 27.5º
ω and φ scans	θmin = 3.0º
Absorption correction: Multi-scan(SORTAV; Blessing, 1997)	h = −7→7
Tmin = 0.956, Tmax = 0.990	k = −15→15
10729 measured reflections	l = −23→23

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)] = 0.039	w = 1/[σ2(Fo2) + (0.0384P)2 + 0.468P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.22 e Å−3
5735 reflections	Δρmin = −0.24 e Å−3
347 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (2)
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	0.34044 (8)	0.05680 (4)	0.28003 (3)	0.03056 (13)
S2	−0.20179 (8)	0.77953 (4)	0.25164 (2)	0.02763 (13)
O1	0.8468 (2)	0.08820 (11)	−0.01137 (7)	0.0305 (3)
O2	0.5602 (2)	0.82229 (11)	0.51122 (7)	0.0325 (3)
O3	0.7588 (3)	0.03225 (11)	0.40424 (8)	0.0333 (3)
H3A	0.752 (4)	0.0567 (19)	0.4491 (13)	0.040*
H3B	0.633 (4)	0.0293 (19)	0.3796 (13)	0.040*
N1	0.6822 (3)	0.01773 (13)	0.20087 (8)	0.0260 (3)
H1A	0.725 (3)	−0.0312 (17)	0.2307 (11)	0.031*
N2	0.7734 (3)	0.03375 (13)	0.13290 (8)	0.0268 (3)
N3	0.4856 (2)	0.11614 (11)	0.14138 (8)	0.0213 (3)
N4	0.0028 (3)	0.87457 (12)	0.38823 (8)	0.0247 (3)
H4A	−0.085 (3)	0.9228 (17)	0.3954 (11)	0.030*
N5	0.1725 (3)	0.86844 (12)	0.44183 (8)	0.0254 (3)
N6	0.1475 (2)	0.74212 (11)	0.34577 (8)	0.0222 (3)
C1	0.5050 (3)	0.06404 (14)	0.20819 (9)	0.0232 (4)
C2	0.6504 (3)	0.09428 (14)	0.09778 (9)	0.0223 (4)
C3	0.6860 (3)	0.13059 (14)	0.02235 (9)	0.0240 (4)
C4	0.5984 (4)	0.19649 (17)	−0.02503 (10)	0.0371 (5)
H4	0.4838	0.2354	−0.0155	0.044*
C5	0.7116 (4)	0.19619 (17)	−0.09219 (11)	0.0393 (5)
H5	0.6871	0.2351	−0.1361	0.047*
C6	0.8591 (3)	0.13059 (16)	−0.08148 (10)	0.0331 (4)
H6	0.9580	0.1156	−0.1173	0.040*
C7	0.3061 (3)	0.17367 (14)	0.12078 (10)	0.0243 (4)
H7A	0.1900	0.1564	0.1574	0.029*
H7B	0.2319	0.1417	0.0705	0.029*
C8	0.3862 (3)	0.30216 (14)	0.11841 (9)	0.0246 (4)
C9	0.5982 (3)	0.36345 (15)	0.14907 (10)	0.0296 (4)
H9	0.7004	0.3246	0.1729	0.035*
C10	0.6630 (4)	0.48138 (16)	0.14531 (11)	0.0371 (5)
H10	0.8090	0.5228	0.1665	0.045*
C11	0.5153 (4)	0.53864 (17)	0.11072 (11)	0.0404 (5)
H11	0.5599	0.6192	0.1079	0.048*
C12	0.3028 (4)	0.47821 (17)	0.08038 (12)	0.0414 (5)
H12	0.2006	0.5174	0.0570	0.050*
C13	0.2381 (3)	0.36062 (16)	0.08393 (11)	0.0335 (4)
H13	0.0918	0.3195	0.0627	0.040*
C14	−0.0174 (3)	0.79991 (14)	0.32916 (9)	0.0223 (4)
C15	0.2585 (3)	0.78665 (14)	0.41473 (9)	0.0233 (4)
C16	0.4402 (3)	0.74833 (15)	0.45380 (9)	0.0242 (4)
C17	0.5195 (3)	0.65286 (16)	0.44984 (10)	0.0303 (4)
H17	0.4653	0.5884	0.4151	0.036*
C18	0.7002 (3)	0.66805 (17)	0.50797 (10)	0.0321 (4)
H18	0.7905	0.6157	0.5196	0.039*
C19	0.7177 (3)	0.77051 (17)	0.54297 (11)	0.0332 (4)
H19	0.8252	0.8028	0.5843	0.040*
C20	0.2004 (3)	0.65628 (14)	0.29446 (9)	0.0239 (4)
H20A	0.3674	0.6670	0.2974	0.029*
H20B	0.1489	0.6693	0.2422	0.029*
C21	0.0932 (3)	0.53434 (14)	0.31051 (9)	0.0226 (4)
C22	0.1902 (3)	0.44799 (16)	0.28516 (10)	0.0307 (4)
H22	0.3270	0.4668	0.2610	0.037*
C23	0.0880 (4)	0.33463 (17)	0.29509 (11)	0.0389 (5)
H23	0.1549	0.2760	0.2774	0.047*
C24	−0.1094 (4)	0.30642 (17)	0.33038 (12)	0.0405 (5)
H24	−0.1788	0.2285	0.3369	0.049*
C25	−0.2063 (4)	0.39117 (18)	0.35627 (12)	0.0410 (5)
H25	−0.3424	0.3719	0.3808	0.049*
C26	−0.1044 (3)	0.50534 (16)	0.34637 (11)	0.0318 (4)
H26	−0.1714	0.5637	0.3644	0.038*

	U11	U22	U33	U12	U13	U23
S1	0.0307 (3)	0.0369 (3)	0.0255 (2)	0.0094 (2)	0.00647 (18)	0.00482 (19)
S2	0.0285 (3)	0.0262 (2)	0.0270 (2)	0.00626 (19)	−0.00410 (18)	0.00176 (17)
O1	0.0316 (7)	0.0369 (7)	0.0265 (6)	0.0140 (6)	0.0061 (5)	0.0016 (5)
O2	0.0357 (8)	0.0306 (7)	0.0296 (7)	0.0091 (6)	−0.0090 (6)	−0.0012 (5)
O3	0.0415 (9)	0.0352 (7)	0.0271 (7)	0.0190 (7)	−0.0012 (6)	−0.0030 (6)
N1	0.0273 (8)	0.0293 (8)	0.0243 (7)	0.0114 (7)	0.0023 (6)	0.0072 (6)
N2	0.0280 (8)	0.0299 (8)	0.0256 (8)	0.0116 (7)	0.0040 (6)	0.0065 (6)
N3	0.0206 (8)	0.0218 (7)	0.0225 (7)	0.0071 (6)	0.0008 (6)	0.0029 (5)
N4	0.0268 (8)	0.0231 (7)	0.0253 (7)	0.0093 (6)	−0.0010 (6)	0.0007 (6)
N5	0.0266 (8)	0.0262 (7)	0.0237 (7)	0.0083 (6)	−0.0019 (6)	0.0009 (6)
N6	0.0233 (8)	0.0199 (7)	0.0232 (7)	0.0055 (6)	0.0011 (6)	0.0008 (6)
C1	0.0241 (9)	0.0213 (8)	0.0230 (8)	0.0044 (7)	−0.0010 (7)	0.0003 (7)
C2	0.0221 (9)	0.0212 (8)	0.0243 (8)	0.0072 (7)	0.0009 (7)	0.0005 (7)
C3	0.0236 (9)	0.0258 (9)	0.0235 (8)	0.0073 (7)	0.0040 (7)	−0.0004 (7)
C4	0.0512 (13)	0.0423 (11)	0.0282 (10)	0.0277 (10)	0.0126 (9)	0.0110 (8)
C5	0.0592 (14)	0.0384 (11)	0.0263 (10)	0.0194 (10)	0.0126 (9)	0.0103 (8)
C6	0.0382 (12)	0.0355 (10)	0.0256 (9)	0.0070 (9)	0.0097 (8)	0.0007 (8)
C7	0.0211 (9)	0.0257 (9)	0.0276 (9)	0.0093 (7)	0.0002 (7)	0.0019 (7)
C8	0.0304 (10)	0.0245 (9)	0.0210 (8)	0.0109 (8)	0.0022 (7)	0.0008 (7)
C9	0.0339 (11)	0.0281 (9)	0.0272 (9)	0.0108 (8)	−0.0036 (8)	0.0004 (7)
C10	0.0440 (12)	0.0290 (10)	0.0328 (10)	0.0016 (9)	−0.0062 (9)	−0.0021 (8)
C11	0.0609 (15)	0.0250 (10)	0.0350 (11)	0.0113 (10)	−0.0012 (10)	0.0037 (8)
C12	0.0549 (14)	0.0336 (11)	0.0405 (11)	0.0231 (10)	−0.0070 (10)	0.0053 (9)
C13	0.0327 (11)	0.0320 (10)	0.0371 (10)	0.0131 (9)	−0.0046 (8)	0.0007 (8)
C14	0.0213 (9)	0.0193 (8)	0.0262 (8)	0.0034 (7)	0.0038 (7)	0.0052 (7)
C15	0.0238 (9)	0.0227 (8)	0.0224 (8)	0.0037 (7)	0.0020 (7)	0.0022 (7)
C16	0.0238 (9)	0.0274 (9)	0.0207 (8)	0.0055 (7)	−0.0001 (7)	0.0013 (7)
C17	0.0305 (10)	0.0340 (10)	0.0280 (9)	0.0123 (8)	0.0009 (8)	−0.0012 (8)
C18	0.0279 (10)	0.0413 (11)	0.0308 (10)	0.0150 (9)	0.0016 (8)	0.0057 (8)
C19	0.0281 (10)	0.0427 (11)	0.0281 (9)	0.0090 (9)	−0.0058 (8)	0.0069 (8)
C20	0.0253 (9)	0.0244 (9)	0.0228 (8)	0.0068 (7)	0.0053 (7)	0.0005 (7)
C21	0.0246 (9)	0.0237 (8)	0.0202 (8)	0.0080 (7)	−0.0001 (7)	0.0011 (7)
C22	0.0390 (11)	0.0327 (10)	0.0248 (9)	0.0165 (9)	0.0043 (8)	0.0012 (7)
C23	0.0612 (15)	0.0280 (10)	0.0306 (10)	0.0201 (10)	−0.0055 (10)	−0.0015 (8)
C24	0.0527 (14)	0.0241 (9)	0.0384 (11)	0.0019 (9)	−0.0137 (10)	0.0062 (8)
C25	0.0339 (12)	0.0383 (11)	0.0485 (12)	0.0020 (9)	0.0050 (9)	0.0146 (10)
C26	0.0296 (11)	0.0277 (9)	0.0402 (11)	0.0091 (8)	0.0085 (8)	0.0049 (8)

S1—C1	1.676 (2)	C8—C9	1.382 (3)
S2—C14	1.682 (2)	C8—C13	1.394 (2)
O1—C6	1.370 (2)	C9—C10	1.389 (3)
O1—C3	1.372 (2)	C9—H9	0.9500
O2—C19	1.364 (2)	C10—C11	1.383 (3)
O2—C16	1.369 (2)	C10—H10	0.9500
O3—H3A	0.85 (2)	C11—C12	1.380 (3)
O3—H3B	0.85 (2)	C11—H11	0.9500
N1—C1	1.339 (2)	C12—C13	1.385 (3)
N1—N2	1.372 (2)	C12—H12	0.9500
N1—H1A	0.88 (2)	C13—H13	0.9500
N2—C2	1.309 (2)	C15—C16	1.440 (2)
N3—C1	1.380 (2)	C16—C17	1.353 (2)
N3—C2	1.380 (2)	C17—C18	1.425 (3)
N3—C7	1.460 (2)	C17—H17	0.9500
N4—C14	1.335 (2)	C18—C19	1.338 (3)
N4—N5	1.370 (2)	C18—H18	0.9500
N4—H4A	0.89 (2)	C19—H19	0.9500
N5—C15	1.314 (2)	C20—C21	1.509 (2)
N6—C14	1.374 (2)	C20—H20A	0.9900
N6—C15	1.378 (2)	C20—H20B	0.9900
N6—C20	1.461 (2)	C21—C26	1.382 (3)
C2—C3	1.447 (2)	C21—C22	1.390 (2)
C3—C4	1.349 (3)	C22—C23	1.386 (3)
C4—C5	1.425 (3)	C22—H22	0.9500
C4—H4	0.9500	C23—C24	1.375 (3)
C5—C6	1.340 (3)	C23—H23	0.9500
C5—H5	0.9500	C24—C25	1.377 (3)
C6—H6	0.9500	C24—H24	0.9500
C7—C8	1.514 (2)	C25—C26	1.394 (3)
C7—H7A	0.9900	C25—H25	0.9500
C7—H7B	0.9900	C26—H26	0.9500
C6—O1—C3	106.50 (14)	C12—C11—H11	120.1
C19—O2—C16	106.33 (14)	C10—C11—H11	120.1
H3A—O3—H3B	108 (2)	C11—C12—C13	120.22 (18)
C1—N1—N2	114.05 (14)	C11—C12—H12	119.9
C1—N1—H1A	126.0 (13)	C13—C12—H12	119.9
N2—N1—H1A	118.8 (13)	C12—C13—C8	120.44 (19)
C2—N2—N1	103.59 (14)	C12—C13—H13	119.8
C1—N3—C2	107.51 (14)	C8—C13—H13	119.8
C1—N3—C7	124.11 (14)	N4—C14—N6	104.29 (14)
C2—N3—C7	128.16 (14)	N4—C14—S2	128.50 (13)
C14—N4—N5	113.20 (14)	N6—C14—S2	127.21 (13)
C14—N4—H4A	126.2 (13)	N5—C15—N6	110.73 (15)
N5—N4—H4A	120.5 (13)	N5—C15—C16	123.67 (15)
C15—N5—N4	104.25 (14)	N6—C15—C16	125.58 (15)
C14—N6—C15	107.53 (14)	C17—C16—O2	109.93 (15)
C14—N6—C20	124.07 (14)	C17—C16—C15	135.42 (16)
C15—N6—C20	128.21 (14)	O2—C16—C15	114.60 (14)
N1—C1—N3	103.46 (14)	C16—C17—C18	106.48 (17)
N1—C1—S1	128.34 (13)	C16—C17—H17	126.8
N3—C1—S1	128.17 (13)	C18—C17—H17	126.8
N2—C2—N3	111.36 (15)	C19—C18—C17	106.48 (16)
N2—C2—C3	122.82 (15)	C19—C18—H18	126.8
N3—C2—C3	125.81 (15)	C17—C18—H18	126.8
C4—C3—O1	109.95 (15)	C18—C19—O2	110.79 (16)
C4—C3—C2	135.93 (17)	C18—C19—H19	124.6
O1—C3—C2	114.11 (15)	O2—C19—H19	124.6
C3—C4—C5	106.47 (17)	N6—C20—C21	114.33 (14)
C3—C4—H4	126.8	N6—C20—H20A	108.7
C5—C4—H4	126.8	C21—C20—H20A	108.7
C6—C5—C4	106.89 (17)	N6—C20—H20B	108.7
C6—C5—H5	126.6	C21—C20—H20B	108.7
C4—C5—H5	126.6	H20A—C20—H20B	107.6
C5—C6—O1	110.20 (16)	C26—C21—C22	119.00 (17)
C5—C6—H6	124.9	C26—C21—C20	122.02 (15)
O1—C6—H6	124.9	C22—C21—C20	118.90 (16)
N3—C7—C8	114.60 (14)	C23—C22—C21	120.24 (19)
N3—C7—H7A	108.6	C23—C22—H22	119.9
C8—C7—H7A	108.6	C21—C22—H22	119.9
N3—C7—H7B	108.6	C24—C23—C22	120.41 (19)
C8—C7—H7B	108.6	C24—C23—H23	119.8
H7A—C7—H7B	107.6	C22—C23—H23	119.8
C9—C8—C13	118.95 (17)	C23—C24—C25	119.95 (19)
C9—C8—C7	122.93 (15)	C23—C24—H24	120.0
C13—C8—C7	118.12 (16)	C25—C24—H24	120.0
C8—C9—C10	120.53 (17)	C24—C25—C26	119.9 (2)
C8—C9—H9	119.7	C24—C25—H25	120.1
C10—C9—H9	119.7	C26—C25—H25	120.1
C11—C10—C9	120.12 (19)	C21—C26—C25	120.52 (18)
C11—C10—H10	119.9	C21—C26—H26	119.7
C9—C10—H10	119.9	C25—C26—H26	119.7
C12—C11—C10	119.73 (18)
C1—N1—N2—C2	1.32 (19)	C7—C8—C13—C12	179.87 (18)
C14—N4—N5—C15	−0.33 (19)	N5—N4—C14—N6	0.32 (19)
N2—N1—C1—N3	−1.84 (19)	N5—N4—C14—S2	−179.83 (13)
N2—N1—C1—S1	176.30 (13)	C15—N6—C14—N4	−0.18 (18)
C2—N3—C1—N1	1.59 (18)	C20—N6—C14—N4	−175.62 (14)
C7—N3—C1—N1	176.47 (14)	C15—N6—C14—S2	179.97 (13)
C2—N3—C1—S1	−176.56 (13)	C20—N6—C14—S2	4.5 (2)
C7—N3—C1—S1	−1.7 (2)	N4—N5—C15—N6	0.20 (19)
N1—N2—C2—N3	−0.20 (19)	N4—N5—C15—C16	−178.34 (16)
N1—N2—C2—C3	−179.37 (16)	C14—N6—C15—N5	−0.02 (19)
C1—N3—C2—N2	−0.90 (19)	C20—N6—C15—N5	175.17 (15)
C7—N3—C2—N2	−175.50 (15)	C14—N6—C15—C16	178.48 (16)
C1—N3—C2—C3	178.23 (16)	C20—N6—C15—C16	−6.3 (3)
C7—N3—C2—C3	3.6 (3)	C19—O2—C16—C17	0.2 (2)
C6—O1—C3—C4	0.6 (2)	C19—O2—C16—C15	177.89 (15)
C6—O1—C3—C2	−179.92 (15)	N5—C15—C16—C17	159.8 (2)
N2—C2—C3—C4	−175.6 (2)	N6—C15—C16—C17	−18.5 (3)
N3—C2—C3—C4	5.4 (3)	N5—C15—C16—O2	−17.1 (2)
N2—C2—C3—O1	5.1 (2)	N6—C15—C16—O2	164.55 (16)
N3—C2—C3—O1	−173.93 (15)	O2—C16—C17—C18	−0.2 (2)
O1—C3—C4—C5	−0.4 (2)	C15—C16—C17—C18	−177.2 (2)
C2—C3—C4—C5	−179.8 (2)	C16—C17—C18—C19	0.1 (2)
C3—C4—C5—C6	0.1 (2)	C17—C18—C19—O2	0.0 (2)
C4—C5—C6—O1	0.3 (2)	C16—O2—C19—C18	−0.1 (2)
C3—O1—C6—C5	−0.5 (2)	C14—N6—C20—C21	−98.91 (19)
C1—N3—C7—C8	111.39 (18)	C15—N6—C20—C21	86.6 (2)
C2—N3—C7—C8	−74.8 (2)	N6—C20—C21—C26	25.8 (2)
N3—C7—C8—C9	−13.9 (2)	N6—C20—C21—C22	−157.33 (16)
N3—C7—C8—C13	166.36 (16)	C26—C21—C22—C23	0.8 (3)
C13—C8—C9—C10	−0.3 (3)	C20—C21—C22—C23	−176.17 (16)
C7—C8—C9—C10	180.00 (17)	C21—C22—C23—C24	−0.3 (3)
C8—C9—C10—C11	0.0 (3)	C22—C23—C24—C25	−0.2 (3)
C9—C10—C11—C12	0.4 (3)	C23—C24—C25—C26	0.2 (3)
C10—C11—C12—C13	−0.5 (3)	C22—C21—C26—C25	−0.7 (3)
C11—C12—C13—C8	0.3 (3)	C20—C21—C26—C25	176.14 (17)
C9—C8—C13—C12	0.1 (3)	C24—C25—C26—C21	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N5i	0.85 (2)	2.08 (2)	2.906 (2)	165 (2)
N1—H1A···S2ii	0.88 (2)	2.47 (2)	3.267 (2)	151 (2)
N4—H4A···O3iii	0.89 (2)	1.81 (2)	2.697 (2)	174 (2)
C7—H7A···N2iv	0.99	2.60	3.304 (3)	128
C7—H7B···O1iv	0.99	2.59	3.440 (2)	144
O3—H3B···S1	0.85 (2)	2.50 (2)	3.320 (2)	162 (2)
C7—H7A···S1	0.99	2.74	3.237 (2)	112
C9—H9···N3	0.95	2.56	2.893 (2)	101
C26—H26···N6	0.95	2.58	2.903 (3)	100
C20—H20B···S2	0.99	2.78	3.214 (2)	107

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N5i	0.85 (2)	2.08 (2)	2.906 (2)	165 (2)
N1—H1A⋯S2ii	0.88 (2)	2.47 (2)	3.267 (2)	151 (2)
N4—H4A⋯O3iii	0.89 (2)	1.81 (2)	2.697 (2)	174 (2)
C7—H7A⋯N2iv	0.99	2.60	3.304 (3)	128
C7—H7B⋯O1iv	0.99	2.59	3.440 (2)	144
O3—H3B⋯S1	0.85 (2)	2.50 (2)	3.320 (2)	162 (2)
C7—H7A⋯S1	0.99	2.74	3.237 (2)	112
C9—H9⋯N3	0.95	2.56	2.893 (2)	101
C26—H26⋯N6	0.95	2.58	2.903 (3)	100
C20—H20B⋯S2	0.99	2.78	3.214 (2)	107

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