(S)-N-[1-(5-Benzyl-sulfan-yl-1,3,4-oxa-diazol-2-yl)-2-phenyl-eth-yl]-4-methyl-benzene-sulfonamide.

The title compound, C(24)H(23)N(3)O(3)S(2), crystallizes with two independent mol-ecules in the asymmetric unit. They differ essentially in the orientation of the tolyl rings, between which there is π-π stacking (centroid-centroid distance = 3.01 Å). The absolute configuration was confirmed by the determination of the Flack parameter [x = 0.008 (9)]. In the crystal, mol-ecules are connected by two classical N-H⋯N hydrogen bonds and two weak but very short C-H⋯O(sulfon-yl) inter-actions, forming layers lying parallel to the bc plane.

Related literature

For the biological activity of substituted-1,3,4-oxadiazo­les, see: Aboraia et al. (2006 ▶); Akhtar et al. (2008 ▶, 2010 ▶); Iqbal et al. (2006 ▶); Syed et al. (2011a ▶); Zahid et al. (2009 ▶); Zareef et al. (2007 ▶); Zarghi et al. (2005 ▶). For the crystal structure of the 4-methyl derivative (which has a methyl instead of a phenylmethyl substituent at C6), see: Syed et al. (2011b ▶). For the synthesis of the title compound, see: Syed et al. (2011a ▶). For information concerning the program RPLUTO, see: CCDC (2007 ▶).

Experimental

Crystal data

C24H23N3O3S2

M = 465.57

Monoclinic,

a = 41.128 (2) Å

b = 5.7205 (5) Å

c = 18.9783 (11) Å

β = 90.940 (4)°

V = 4464.5 (5) Å3

Z = 8

Cu Kα radiation

μ = 2.43 mm−1

T = 100 K

0.25 × 0.08 × 0.03 mm

Data collection

Oxford Diffraction Xcalibur Nova A diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.740, T max = 1.000

42976 measured reflections

8447 independent reflections

7718 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.080

S = 1.04

8447 reflections

587 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 3306 Friedel pairs

Flack parameter: 0.008 (9)

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040669/su2319sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040669/su2319Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811040669/su2319Isup3.cml

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

C24H23N3O3S2	F(000) = 1952
Mr = 465.57	Dx = 1.385 Mg m−3
Monoclinic, C2	Cu Kα radiation, λ = 1.54184 Å
a = 41.128 (2) Å	Cell parameters from 19219 reflections
b = 5.7205 (5) Å	θ = 3.1–75.7°
c = 18.9783 (11) Å	µ = 2.43 mm−1
β = 90.940 (4)°	T = 100 K
V = 4464.5 (5) Å3	Lath, colourless
Z = 8	0.25 × 0.08 × 0.03 mm

Oxford Diffraction Xcalibur Nova A diffractometer	8447 independent reflections
Radiation source: Nova (Cu) X-ray Source	7718 reflections with I > 2σ(I)
mirror	Rint = 0.049
Detector resolution: 10.3543 pixels mm-1	θmax = 76.0°, θmin = 3.1°
ω–scan	h = −50→51
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −7→6
Tmin = 0.740, Tmax = 1.000	l = −23→23
42976 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.080	w = 1/[σ2(Fo2) + (0.0523P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
8447 reflections	Δρmax = 0.27 e Å−3
587 parameters	Δρmin = −0.21 e Å−3
1 restraint	Absolute structure: Flack (1983), 3306 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.008 (9)

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	0.166517 (10)	0.47595 (8)	0.20778 (2)	0.02157 (10)
S2	0.167054 (11)	0.78799 (10)	0.51291 (2)	0.02831 (11)
O1	0.13716 (3)	0.6557 (2)	0.39040 (6)	0.0230 (3)
C2	0.14887 (4)	0.8364 (3)	0.43097 (9)	0.0230 (4)
N3	0.14640 (4)	1.0359 (3)	0.40067 (8)	0.0266 (3)
N4	0.13278 (4)	0.9900 (3)	0.33309 (8)	0.0229 (3)
C5	0.12768 (4)	0.7679 (4)	0.32999 (9)	0.0209 (4)
N5	0.13242 (4)	0.4323 (3)	0.24788 (8)	0.0232 (3)
H05	0.1322 (6)	0.318 (5)	0.2709 (12)	0.030 (6)*
O2	0.16115 (3)	0.6639 (3)	0.15920 (6)	0.0261 (3)
O3	0.17624 (3)	0.2503 (3)	0.18271 (6)	0.0268 (3)
C6	0.11270 (4)	0.6305 (3)	0.27056 (10)	0.0227 (4)
H6	0.1097	0.7381	0.2294	0.027*
C7	0.07905 (5)	0.5358 (4)	0.29039 (10)	0.0272 (4)
H7A	0.0699	0.4442	0.2505	0.033*
H7B	0.0815	0.4296	0.3313	0.033*
C8	0.05586 (4)	0.7294 (4)	0.30833 (10)	0.0255 (4)
C9	0.04399 (4)	0.8782 (4)	0.25553 (10)	0.0279 (4)
H9	0.0506	0.8553	0.2083	0.033*
C10	0.02279 (5)	1.0582 (4)	0.27069 (11)	0.0308 (4)
H10	0.0147	1.1566	0.2341	0.037*
C11	0.01329 (5)	1.0945 (4)	0.34032 (12)	0.0345 (5)
H11	−0.0011	1.2188	0.3514	0.041*
C12	0.02501 (5)	0.9474 (5)	0.39293 (11)	0.0387 (5)
H12	0.0184	0.9699	0.4401	0.046*
C13	0.04630 (5)	0.7682 (5)	0.37735 (11)	0.0348 (5)
H13	0.0545	0.6708	0.4141	0.042*
C14	0.19511 (4)	0.5712 (4)	0.27153 (9)	0.0227 (4)
C15	0.20295 (5)	0.4229 (4)	0.32732 (10)	0.0269 (4)
H15	0.1929	0.2739	0.3309	0.032*
C16	0.22558 (5)	0.4952 (4)	0.37751 (10)	0.0305 (4)
H16	0.2311	0.3940	0.4155	0.037*
C17	0.24035 (4)	0.7134 (4)	0.37338 (10)	0.0278 (4)
C18	0.23229 (5)	0.8570 (4)	0.31670 (10)	0.0278 (4)
H18	0.2426	1.0049	0.3127	0.033*
C19	0.20954 (4)	0.7895 (4)	0.26571 (9)	0.0258 (4)
H19	0.2040	0.8907	0.2277	0.031*
C20	0.26377 (5)	0.7947 (5)	0.42984 (10)	0.0376 (5)
H20A	0.2517	0.8419	0.4716	0.056*
H20B	0.2762	0.9281	0.4124	0.056*
H20C	0.2787	0.6670	0.4423	0.056*
C21	0.14683 (5)	0.5189 (4)	0.53937 (10)	0.0292 (4)
H21A	0.1511	0.3969	0.5037	0.035*
H21B	0.1565	0.4655	0.5846	0.035*
C22	0.11060 (5)	0.5414 (4)	0.54782 (9)	0.0275 (4)
C23	0.09059 (6)	0.3627 (4)	0.52384 (11)	0.0358 (5)
H23	0.0998	0.2311	0.5011	0.043*
C24	0.05716 (6)	0.3738 (5)	0.53275 (13)	0.0428 (6)
H24	0.0438	0.2485	0.5169	0.051*
C25	0.04327 (5)	0.5660 (4)	0.56454 (11)	0.0367 (5)
H25	0.0204	0.5744	0.5701	0.044*
C26	0.06304 (5)	0.7455 (4)	0.58817 (10)	0.0347 (5)
H26	0.0537	0.8783	0.6100	0.042*
C27	0.09657 (5)	0.7340 (4)	0.58035 (10)	0.0318 (5)
H27	0.1099	0.8580	0.5973	0.038*
S1'	0.321235 (10)	0.48913 (9)	0.28913 (2)	0.02305 (10)
S2'	0.339409 (11)	0.78665 (9)	−0.01838 (2)	0.02753 (11)
O1'	0.36121 (3)	0.6560 (2)	0.11112 (6)	0.0220 (3)
C2'	0.35354 (4)	0.8379 (4)	0.06659 (10)	0.0237 (4)
N3'	0.35610 (4)	1.0389 (3)	0.09662 (8)	0.0252 (3)
N4'	0.36541 (4)	0.9927 (3)	0.16741 (8)	0.0233 (3)
C5'	0.36816 (4)	0.7694 (4)	0.17275 (9)	0.0222 (4)
N5'	0.35627 (4)	0.4383 (3)	0.25289 (8)	0.0233 (3)
H05'	0.3569 (5)	0.323 (5)	0.2274 (11)	0.023 (6)*
O2'	0.32614 (3)	0.6908 (3)	0.33283 (7)	0.0294 (3)
O3'	0.31089 (3)	0.2714 (3)	0.31844 (7)	0.0296 (3)
C6'	0.37862 (4)	0.6282 (3)	0.23546 (9)	0.0224 (4)
H6'	0.3804	0.7352	0.2770	0.027*
C7'	0.41243 (4)	0.5204 (4)	0.22288 (10)	0.0258 (4)
H7'1	0.4202	0.4406	0.2663	0.031*
H7'2	0.4108	0.4025	0.1848	0.031*
C8'	0.43648 (4)	0.7080 (4)	0.20266 (10)	0.0250 (4)
C9'	0.44705 (4)	0.8726 (4)	0.25207 (10)	0.0273 (4)
H9'	0.4398	0.8620	0.2992	0.033*
C10'	0.46791 (5)	1.0508 (4)	0.23364 (11)	0.0306 (4)
H10'	0.4750	1.1612	0.2680	0.037*
C11'	0.47863 (5)	1.0687 (4)	0.16422 (12)	0.0344 (5)
H11'	0.4929	1.1910	0.1511	0.041*
C12'	0.46813 (5)	0.9063 (4)	0.11491 (12)	0.0359 (5)
H12'	0.4753	0.9178	0.0677	0.043*
C13'	0.44723 (5)	0.7261 (4)	0.13372 (10)	0.0314 (5)
H13'	0.4403	0.6152	0.0994	0.038*
C14'	0.29307 (5)	0.5646 (4)	0.22125 (10)	0.0239 (4)
C15'	0.27134 (4)	0.3988 (4)	0.19568 (10)	0.0251 (4)
H15'	0.2708	0.2471	0.2160	0.030*
C16'	0.25036 (4)	0.4563 (4)	0.13994 (10)	0.0270 (4)
H16'	0.2352	0.3435	0.1231	0.032*
C17'	0.25124 (4)	0.6745 (4)	0.10860 (10)	0.0257 (4)
C18'	0.27325 (4)	0.8394 (4)	0.13545 (10)	0.0255 (4)
H18'	0.2744	0.9894	0.1142	0.031*
C19'	0.29351 (4)	0.7883 (4)	0.19256 (9)	0.0254 (4)
H19'	0.3075	0.9047	0.2118	0.030*
C20'	0.22829 (5)	0.7398 (4)	0.04908 (10)	0.0320 (5)
H20D	0.2161	0.6012	0.0338	0.048*
H20E	0.2407	0.8009	0.0095	0.048*
H20F	0.2131	0.8598	0.0652	0.048*
C21'	0.35966 (5)	0.5122 (4)	−0.03843 (10)	0.0277 (4)
H21C	0.3552	0.3993	−0.0003	0.033*
H21D	0.3501	0.4483	−0.0826	0.033*
C22'	0.39605 (5)	0.5307 (4)	−0.04671 (9)	0.0261 (4)
C23'	0.41558 (5)	0.3493 (4)	−0.02205 (11)	0.0331 (5)
H23'	0.4061	0.2206	0.0015	0.040*
C24'	0.44899 (6)	0.3552 (5)	−0.03170 (12)	0.0386 (5)
H24'	0.4621	0.2291	−0.0154	0.046*
C25'	0.46332 (5)	0.5443 (4)	−0.06506 (11)	0.0339 (5)
H25'	0.4862	0.5491	−0.0711	0.041*
C26'	0.44391 (5)	0.7253 (4)	−0.08939 (11)	0.0347 (5)
H26'	0.4535	0.8551	−0.1123	0.042*
C27'	0.41052 (5)	0.7189 (4)	−0.08060 (10)	0.0318 (4)
H27'	0.3974	0.8438	−0.0978	0.038*

	U11	U22	U33	U12	U13	U23
S1	0.0286 (2)	0.0198 (2)	0.01621 (18)	0.00177 (19)	−0.00120 (14)	0.00067 (18)
S2	0.0317 (2)	0.0313 (3)	0.0218 (2)	−0.0015 (2)	−0.00495 (16)	−0.0002 (2)
O1	0.0299 (6)	0.0196 (7)	0.0196 (6)	−0.0007 (5)	−0.0029 (5)	0.0012 (5)
C2	0.0249 (8)	0.0210 (11)	0.0232 (9)	−0.0003 (7)	0.0023 (7)	−0.0021 (7)
N3	0.0318 (8)	0.0233 (9)	0.0245 (7)	−0.0026 (6)	−0.0021 (6)	−0.0026 (7)
N4	0.0289 (7)	0.0197 (8)	0.0202 (7)	−0.0016 (7)	−0.0003 (5)	0.0016 (7)
C5	0.0222 (8)	0.0212 (10)	0.0192 (8)	0.0021 (7)	−0.0005 (6)	0.0029 (7)
N5	0.0305 (8)	0.0164 (9)	0.0225 (8)	0.0001 (6)	−0.0030 (6)	0.0010 (7)
O2	0.0349 (7)	0.0243 (8)	0.0192 (6)	0.0023 (6)	−0.0033 (5)	0.0043 (6)
O3	0.0355 (7)	0.0242 (8)	0.0207 (6)	0.0034 (6)	−0.0013 (5)	−0.0037 (5)
C6	0.0256 (9)	0.0189 (10)	0.0237 (8)	0.0018 (7)	−0.0015 (7)	0.0023 (7)
C7	0.0282 (9)	0.0237 (11)	0.0296 (9)	−0.0020 (8)	−0.0031 (7)	0.0026 (8)
C8	0.0225 (8)	0.0280 (11)	0.0260 (9)	−0.0042 (8)	−0.0019 (7)	−0.0001 (8)
C9	0.0243 (9)	0.0322 (11)	0.0272 (9)	−0.0019 (8)	−0.0014 (7)	0.0020 (8)
C10	0.0265 (9)	0.0317 (12)	0.0339 (10)	0.0001 (8)	−0.0031 (8)	0.0026 (9)
C11	0.0277 (9)	0.0323 (13)	0.0436 (12)	0.0013 (9)	0.0024 (8)	−0.0072 (10)
C12	0.0370 (11)	0.0508 (16)	0.0285 (10)	−0.0019 (10)	0.0046 (8)	−0.0098 (10)
C13	0.0337 (10)	0.0422 (14)	0.0284 (9)	0.0001 (10)	−0.0006 (8)	0.0033 (10)
C14	0.0261 (8)	0.0227 (10)	0.0192 (8)	0.0023 (7)	0.0009 (7)	−0.0016 (7)
C15	0.0301 (9)	0.0273 (12)	0.0232 (9)	−0.0019 (7)	−0.0021 (7)	0.0028 (8)
C16	0.0338 (10)	0.0367 (12)	0.0208 (8)	0.0016 (10)	−0.0042 (7)	0.0036 (9)
C17	0.0243 (9)	0.0367 (12)	0.0224 (9)	0.0013 (8)	0.0013 (7)	−0.0077 (8)
C18	0.0295 (9)	0.0241 (11)	0.0300 (10)	−0.0023 (8)	0.0023 (7)	−0.0045 (8)
C19	0.0293 (9)	0.0232 (10)	0.0249 (8)	0.0018 (8)	0.0019 (7)	0.0019 (8)
C20	0.0317 (10)	0.0518 (15)	0.0291 (10)	−0.0014 (11)	−0.0030 (8)	−0.0094 (11)
C21	0.0369 (10)	0.0283 (12)	0.0224 (9)	0.0026 (8)	−0.0010 (7)	0.0053 (8)
C22	0.0391 (10)	0.0246 (11)	0.0188 (8)	0.0017 (8)	−0.0013 (7)	0.0073 (8)
C23	0.0467 (12)	0.0264 (12)	0.0344 (11)	−0.0006 (10)	0.0009 (9)	−0.0004 (9)
C24	0.0468 (13)	0.0366 (14)	0.0448 (13)	−0.0116 (11)	−0.0028 (10)	0.0031 (11)
C25	0.0347 (11)	0.0443 (14)	0.0310 (10)	−0.0019 (10)	−0.0005 (8)	0.0127 (10)
C26	0.0392 (10)	0.0382 (14)	0.0267 (9)	0.0048 (10)	0.0034 (8)	0.0026 (9)
C27	0.0368 (10)	0.0327 (13)	0.0259 (9)	−0.0011 (9)	−0.0034 (7)	−0.0005 (9)
S1'	0.0299 (2)	0.0215 (2)	0.01781 (19)	−0.0008 (2)	−0.00022 (15)	−0.00065 (18)
S2'	0.0338 (2)	0.0290 (3)	0.0197 (2)	0.0039 (2)	−0.00464 (16)	−0.0004 (2)
O1'	0.0285 (6)	0.0186 (7)	0.0188 (6)	0.0009 (5)	−0.0022 (5)	−0.0009 (5)
C2'	0.0261 (9)	0.0229 (11)	0.0221 (8)	0.0032 (7)	0.0000 (7)	0.0040 (7)
N3'	0.0317 (8)	0.0211 (9)	0.0228 (7)	0.0003 (6)	−0.0011 (6)	0.0014 (6)
N4'	0.0305 (7)	0.0193 (8)	0.0200 (7)	0.0005 (7)	−0.0005 (5)	−0.0006 (7)
C5'	0.0247 (8)	0.0228 (10)	0.0189 (8)	−0.0006 (8)	−0.0016 (6)	−0.0032 (8)
N5'	0.0305 (8)	0.0173 (9)	0.0222 (7)	−0.0011 (6)	−0.0017 (6)	−0.0021 (7)
O2'	0.0363 (7)	0.0295 (8)	0.0224 (6)	0.0004 (6)	−0.0004 (5)	−0.0064 (6)
O3'	0.0368 (7)	0.0288 (8)	0.0232 (6)	−0.0039 (6)	0.0012 (5)	0.0065 (6)
C6'	0.0269 (9)	0.0188 (10)	0.0215 (8)	−0.0015 (7)	−0.0039 (7)	−0.0010 (7)
C7'	0.0271 (9)	0.0225 (11)	0.0276 (9)	0.0030 (8)	−0.0034 (7)	−0.0007 (8)
C8'	0.0234 (8)	0.0252 (11)	0.0265 (9)	0.0037 (7)	−0.0031 (7)	0.0000 (8)
C9'	0.0252 (9)	0.0302 (11)	0.0266 (9)	0.0045 (8)	−0.0004 (7)	−0.0024 (8)
C10'	0.0264 (9)	0.0299 (12)	0.0356 (10)	0.0004 (8)	−0.0014 (8)	−0.0058 (9)
C11'	0.0304 (10)	0.0294 (12)	0.0435 (12)	−0.0003 (9)	0.0030 (9)	0.0059 (10)
C12'	0.0399 (11)	0.0377 (14)	0.0303 (10)	0.0034 (9)	0.0023 (8)	0.0055 (9)
C13'	0.0312 (9)	0.0364 (13)	0.0266 (9)	0.0038 (9)	−0.0018 (7)	−0.0049 (9)
C14'	0.0279 (9)	0.0212 (10)	0.0226 (8)	0.0019 (7)	0.0020 (7)	−0.0015 (7)
C15'	0.0293 (9)	0.0218 (10)	0.0244 (9)	0.0007 (7)	0.0035 (7)	0.0002 (8)
C16'	0.0267 (9)	0.0269 (11)	0.0272 (9)	−0.0014 (8)	−0.0008 (7)	−0.0026 (8)
C17'	0.0234 (9)	0.0278 (11)	0.0261 (9)	0.0023 (8)	0.0032 (7)	−0.0023 (8)
C18'	0.0278 (9)	0.0221 (11)	0.0268 (9)	0.0004 (7)	0.0030 (7)	0.0013 (7)
C19'	0.0264 (8)	0.0232 (10)	0.0265 (8)	−0.0002 (8)	0.0008 (7)	−0.0018 (8)
C20'	0.0318 (10)	0.0330 (13)	0.0311 (10)	−0.0006 (9)	−0.0048 (8)	0.0000 (9)
C21'	0.0350 (10)	0.0265 (11)	0.0216 (8)	−0.0005 (8)	−0.0028 (7)	−0.0067 (8)
C22'	0.0365 (10)	0.0248 (11)	0.0171 (8)	−0.0010 (8)	−0.0001 (7)	−0.0056 (8)
C23'	0.0421 (11)	0.0256 (12)	0.0315 (10)	0.0039 (9)	0.0011 (8)	0.0005 (9)
C24'	0.0401 (12)	0.0360 (13)	0.0397 (12)	0.0119 (10)	−0.0015 (9)	−0.0002 (10)
C25'	0.0340 (10)	0.0389 (13)	0.0288 (10)	0.0007 (9)	0.0008 (8)	−0.0074 (9)
C26'	0.0391 (11)	0.0352 (13)	0.0299 (10)	−0.0046 (9)	0.0025 (8)	−0.0009 (9)
C27'	0.0381 (10)	0.0284 (12)	0.0288 (10)	0.0006 (9)	−0.0015 (8)	0.0005 (8)

S1—O2	1.4312 (14)	C15'—C16'	1.394 (3)
S1—O3	1.4351 (15)	C16'—C17'	1.383 (3)
S1—N5	1.6256 (17)	C17'—C18'	1.398 (3)
S1—C14	1.7597 (19)	C17'—C20'	1.507 (3)
S2—C2	1.7368 (19)	C18'—C19'	1.387 (3)
S2—C21	1.824 (2)	C21'—C22'	1.511 (3)
O1—C5	1.365 (2)	C22'—C23'	1.389 (3)
O1—C2	1.371 (2)	C22'—C27'	1.392 (3)
C2—N3	1.281 (3)	C23'—C24'	1.389 (3)
N3—N4	1.416 (2)	C24'—C25'	1.390 (3)
N4—C5	1.289 (3)	C25'—C26'	1.382 (3)
C5—C6	1.499 (3)	C26'—C27'	1.387 (3)
N5—C6	1.463 (2)	N5—H05	0.79 (3)
C6—C7	1.539 (3)	C6—H6	1.0000
C7—C8	1.504 (3)	C7—H7A	0.9900
C8—C13	1.392 (3)	C7—H7B	0.9900
C8—C9	1.397 (3)	C9—H9	0.9500
C9—C10	1.383 (3)	C10—H10	0.9500
C10—C11	1.400 (3)	C11—H11	0.9500
C11—C12	1.386 (3)	C12—H12	0.9500
C12—C13	1.383 (3)	C13—H13	0.9500
C14—C19	1.388 (3)	C15—H15	0.9500
C14—C15	1.391 (3)	C16—H16	0.9500
C15—C16	1.384 (3)	C18—H18	0.9500
C16—C17	1.391 (3)	C19—H19	0.9500
C17—C18	1.389 (3)	C20—H20A	0.9800
C17—C20	1.503 (3)	C20—H20B	0.9800
C18—C19	1.390 (3)	C20—H20C	0.9800
C21—C22	1.507 (3)	C21—H21A	0.9900
C22—C23	1.385 (3)	C21—H21B	0.9900
C22—C27	1.393 (3)	C23—H23	0.9500
C23—C24	1.389 (3)	C24—H24	0.9500
C24—C25	1.382 (4)	C25—H25	0.9500
C25—C26	1.380 (3)	C26—H26	0.9500
C26—C27	1.391 (3)	C27—H27	0.9500
S1'—O3'	1.4316 (15)	N5'—H05'	0.82 (3)
S1'—O2'	1.4331 (15)	C6'—H6'	1.0000
S1'—N5'	1.6329 (16)	C7'—H7'1	0.9900
S1'—C14'	1.772 (2)	C7'—H7'2	0.9900
S2'—C2'	1.7302 (19)	C9'—H9'	0.9500
S2'—C21'	1.820 (2)	C10'—H10'	0.9500
O1'—C5'	1.364 (2)	C11'—H11'	0.9500
O1'—C2'	1.374 (2)	C12'—H12'	0.9500
C2'—N3'	1.287 (3)	C13'—H13'	0.9500
N3'—N4'	1.416 (2)	C15'—H15'	0.9500
N4'—C5'	1.286 (3)	C16'—H16'	0.9500
C5'—C6'	1.496 (3)	C18'—H18'	0.9500
N5'—C6'	1.465 (2)	C19'—H19'	0.9500
C6'—C7'	1.543 (3)	C20'—H20D	0.9800
C7'—C8'	1.513 (3)	C20'—H20E	0.9800
C8'—C13'	1.392 (3)	C20'—H20F	0.9800
C8'—C9'	1.393 (3)	C21'—H21C	0.9900
C9'—C10'	1.381 (3)	C21'—H21D	0.9900
C10'—C11'	1.400 (3)	C23'—H23'	0.9500
C11'—C12'	1.383 (3)	C24'—H24'	0.9500
C12'—C13'	1.392 (3)	C25'—H25'	0.9500
C14'—C15'	1.385 (3)	C26'—H26'	0.9500
C14'—C19'	1.391 (3)	C27'—H27'	0.9500
O2—S1—O3	120.22 (8)	S1—N5—H05	113.8 (17)
O2—S1—N5	106.96 (8)	N5—C6—H6	108.0
O3—S1—N5	105.33 (8)	C5—C6—H6	108.0
O2—S1—C14	107.74 (9)	C7—C6—H6	108.0
O3—S1—C14	108.64 (9)	C8—C7—H7A	109.2
N5—S1—C14	107.31 (8)	C6—C7—H7A	109.2
C2—S2—C21	100.92 (9)	C8—C7—H7B	109.2
C5—O1—C2	102.11 (15)	C6—C7—H7B	109.2
N3—C2—O1	113.26 (16)	H7A—C7—H7B	107.9
N3—C2—S2	125.00 (15)	C10—C9—H9	119.4
O1—C2—S2	121.64 (14)	C8—C9—H9	119.4
C2—N3—N4	105.59 (16)	C9—C10—H10	120.2
C5—N4—N3	106.60 (15)	C11—C10—H10	120.2
N4—C5—O1	112.41 (16)	C12—C11—H11	120.3
N4—C5—C6	128.00 (17)	C10—C11—H11	120.3
O1—C5—C6	119.57 (17)	C13—C12—H12	119.7
C6—N5—S1	120.36 (13)	C11—C12—H12	119.7
N5—C6—C5	113.87 (15)	C12—C13—H13	119.7
N5—C6—C7	107.71 (16)	C8—C13—H13	119.7
C5—C6—C7	111.15 (15)	C16—C15—H15	120.4
C8—C7—C6	111.85 (16)	C14—C15—H15	120.4
C13—C8—C9	118.5 (2)	C15—C16—H16	119.4
C13—C8—C7	121.37 (19)	C17—C16—H16	119.4
C9—C8—C7	120.12 (17)	C17—C18—H18	119.2
C10—C9—C8	121.25 (18)	C19—C18—H18	119.2
C9—C10—C11	119.6 (2)	C14—C19—H19	120.7
C12—C11—C10	119.4 (2)	C18—C19—H19	120.7
C13—C12—C11	120.64 (19)	C17—C20—H20A	109.5
C12—C13—C8	120.6 (2)	C17—C20—H20B	109.5
C19—C14—C15	121.02 (18)	H20A—C20—H20B	109.5
C19—C14—S1	120.38 (15)	C17—C20—H20C	109.5
C15—C14—S1	118.60 (16)	H20A—C20—H20C	109.5
C16—C15—C14	119.1 (2)	H20B—C20—H20C	109.5
C15—C16—C17	121.26 (19)	C22—C21—H21A	108.7
C18—C17—C16	118.38 (18)	S2—C21—H21A	108.7
C18—C17—C20	120.8 (2)	C22—C21—H21B	108.7
C16—C17—C20	120.8 (2)	S2—C21—H21B	108.7
C17—C18—C19	121.6 (2)	H21A—C21—H21B	107.6
C14—C19—C18	118.59 (18)	C22—C23—H23	119.7
C22—C21—S2	114.43 (15)	C24—C23—H23	119.7
C23—C22—C27	118.79 (19)	C25—C24—H24	119.8
C23—C22—C21	119.0 (2)	C23—C24—H24	119.8
C27—C22—C21	122.16 (19)	C26—C25—H25	120.4
C22—C23—C24	120.7 (2)	C24—C25—H25	120.4
C25—C24—C23	120.4 (2)	C25—C26—H26	119.7
C26—C25—C24	119.2 (2)	C27—C26—H26	119.7
C25—C26—C27	120.7 (2)	C26—C27—H27	119.9
C26—C27—C22	120.2 (2)	C22—C27—H27	119.9
O3'—S1'—O2'	121.04 (8)	C6'—N5'—H05'	116.1 (15)
O3'—S1'—N5'	106.17 (9)	S1'—N5'—H05'	115.4 (15)
O2'—S1'—N5'	105.68 (9)	N5'—C6'—H6'	108.2
O3'—S1'—C14'	107.42 (9)	C5'—C6'—H6'	108.2
O2'—S1'—C14'	108.00 (9)	C7'—C6'—H6'	108.2
N5'—S1'—C14'	107.94 (8)	C8'—C7'—H7'1	109.6
C2'—S2'—C21'	101.14 (9)	C6'—C7'—H7'1	109.6
C5'—O1'—C2'	102.12 (15)	C8'—C7'—H7'2	109.6
N3'—C2'—O1'	112.84 (15)	C6'—C7'—H7'2	109.6
N3'—C2'—S2'	126.02 (15)	H7'1—C7'—H7'2	108.1
O1'—C2'—S2'	120.99 (14)	C10'—C9'—H9'	119.4
C2'—N3'—N4'	105.81 (15)	C8'—C9'—H9'	119.4
C5'—N4'—N3'	106.39 (15)	C9'—C10'—H10'	120.0
N4'—C5'—O1'	112.82 (16)	C11'—C10'—H10'	120.0
N4'—C5'—C6'	128.53 (17)	C12'—C11'—H11'	120.4
O1'—C5'—C6'	118.62 (17)	C10'—C11'—H11'	120.4
C6'—N5'—S1'	121.64 (13)	C11'—C12'—H12'	119.6
N5'—C6'—C5'	114.01 (15)	C13'—C12'—H12'	119.6
N5'—C6'—C7'	108.00 (16)	C8'—C13'—H13'	119.9
C5'—C6'—C7'	109.93 (15)	C12'—C13'—H13'	119.9
C8'—C7'—C6'	110.48 (17)	C14'—C15'—H15'	120.3
C13'—C8'—C9'	118.82 (19)	C16'—C15'—H15'	120.3
C13'—C8'—C7'	120.67 (18)	C17'—C16'—H16'	119.4
C9'—C8'—C7'	120.44 (17)	C15'—C16'—H16'	119.4
C10'—C9'—C8'	121.10 (18)	C19'—C18'—H18'	119.3
C9'—C10'—C11'	119.9 (2)	C17'—C18'—H18'	119.3
C12'—C11'—C10'	119.2 (2)	C18'—C19'—H19'	120.4
C11'—C12'—C13'	120.7 (2)	C14'—C19'—H19'	120.4
C8'—C13'—C12'	120.2 (2)	C17'—C20'—H20D	109.5
C15'—C14'—C19'	120.34 (18)	C17'—C20'—H20E	109.5
C15'—C14'—S1'	119.89 (16)	H20D—C20'—H20E	109.5
C19'—C14'—S1'	119.75 (15)	C17'—C20'—H20F	109.5
C14'—C15'—C16'	119.49 (19)	H20D—C20'—H20F	109.5
C17'—C16'—C15'	121.26 (19)	H20E—C20'—H20F	109.5
C16'—C17'—C18'	118.27 (17)	C22'—C21'—H21C	108.6
C16'—C17'—C20'	121.69 (18)	S2'—C21'—H21C	108.6
C18'—C17'—C20'	119.99 (19)	C22'—C21'—H21D	108.6
C19'—C18'—C17'	121.31 (19)	S2'—C21'—H21D	108.6
C18'—C19'—C14'	119.22 (19)	H21C—C21'—H21D	107.6
C22'—C21'—S2'	114.75 (15)	C22'—C23'—H23'	119.8
C23'—C22'—C27'	118.94 (19)	C24'—C23'—H23'	119.8
C23'—C22'—C21'	118.76 (19)	C23'—C24'—H24'	119.8
C27'—C22'—C21'	122.25 (19)	C25'—C24'—H24'	119.8
C22'—C23'—C24'	120.4 (2)	C26'—C25'—H25'	120.4
C23'—C24'—C25'	120.4 (2)	C24'—C25'—H25'	120.4
C26'—C25'—C24'	119.2 (2)	C25'—C26'—H26'	119.7
C25'—C26'—C27'	120.5 (2)	C27'—C26'—H26'	119.7
C26'—C27'—C22'	120.5 (2)	C26'—C27'—H27'	119.7
C6—N5—H05	118.1 (17)	C22'—C27'—H27'	119.7
C5—O1—C2—N3	1.28 (19)	C5'—O1'—C2'—N3'	1.21 (19)
C5—O1—C2—S2	−175.38 (13)	C5'—O1'—C2'—S2'	−174.64 (13)
C21—S2—C2—N3	155.78 (17)	C21'—S2'—C2'—N3'	154.33 (17)
C21—S2—C2—O1	−27.96 (16)	C21'—S2'—C2'—O1'	−30.40 (16)
O1—C2—N3—N4	−1.7 (2)	O1'—C2'—N3'—N4'	−1.5 (2)
S2—C2—N3—N4	174.82 (13)	S2'—C2'—N3'—N4'	174.09 (13)
C2—N3—N4—C5	1.46 (19)	C2'—N3'—N4'—C5'	1.2 (2)
N3—N4—C5—O1	−0.72 (19)	N3'—N4'—C5'—O1'	−0.5 (2)
N3—N4—C5—C6	178.11 (16)	N3'—N4'—C5'—C6'	177.52 (17)
C2—O1—C5—N4	−0.26 (19)	C2'—O1'—C5'—N4'	−0.37 (19)
C2—O1—C5—C6	−179.19 (15)	C2'—O1'—C5'—C6'	−178.60 (15)
O2—S1—N5—C6	−41.23 (16)	O3'—S1'—N5'—C6'	−162.24 (14)
O3—S1—N5—C6	−170.22 (14)	O2'—S1'—N5'—C6'	−32.52 (16)
C14—S1—N5—C6	74.15 (16)	C14'—S1'—N5'—C6'	82.83 (16)
S1—N5—C6—C5	−69.23 (19)	S1'—N5'—C6'—C5'	−73.65 (19)
S1—N5—C6—C7	167.03 (13)	S1'—N5'—C6'—C7'	163.85 (13)
N4—C5—C6—N5	127.40 (19)	N4'—C5'—C6'—N5'	128.6 (2)
O1—C5—C6—N5	−53.8 (2)	O1'—C5'—C6'—N5'	−53.4 (2)
N4—C5—C6—C7	−110.7 (2)	N4'—C5'—C6'—C7'	−109.9 (2)
O1—C5—C6—C7	68.0 (2)	O1'—C5'—C6'—C7'	68.0 (2)
N5—C6—C7—C8	−174.88 (15)	N5'—C6'—C7'—C8'	178.48 (15)
C5—C6—C7—C8	59.7 (2)	C5'—C6'—C7'—C8'	53.5 (2)
C6—C7—C8—C13	−108.3 (2)	C6'—C7'—C8'—C13'	−107.2 (2)
C6—C7—C8—C9	70.2 (2)	C6'—C7'—C8'—C9'	69.8 (2)
C13—C8—C9—C10	−1.1 (3)	C13'—C8'—C9'—C10'	−0.2 (3)
C7—C8—C9—C10	−179.66 (18)	C7'—C8'—C9'—C10'	−177.21 (18)
C8—C9—C10—C11	0.8 (3)	C8'—C9'—C10'—C11'	0.3 (3)
C9—C10—C11—C12	−0.8 (3)	C9'—C10'—C11'—C12'	−0.1 (3)
C10—C11—C12—C13	1.0 (3)	C10'—C11'—C12'—C13'	−0.2 (3)
C11—C12—C13—C8	−1.3 (4)	C9'—C8'—C13'—C12'	−0.1 (3)
C9—C8—C13—C12	1.3 (3)	C7'—C8'—C13'—C12'	176.88 (19)
C7—C8—C13—C12	179.86 (19)	C11'—C12'—C13'—C8'	0.3 (3)
O2—S1—C14—C19	−4.05 (17)	O3'—S1'—C14'—C15'	−13.95 (17)
O3—S1—C14—C19	127.68 (15)	O2'—S1'—C14'—C15'	−146.02 (15)
N5—S1—C14—C19	−118.91 (15)	N5'—S1'—C14'—C15'	100.16 (16)
O2—S1—C14—C15	176.24 (14)	O3'—S1'—C14'—C19'	167.84 (14)
O3—S1—C14—C15	−52.03 (17)	O2'—S1'—C14'—C19'	35.77 (16)
N5—S1—C14—C15	61.38 (17)	N5'—S1'—C14'—C19'	−78.05 (16)
C19—C14—C15—C16	−0.2 (3)	C19'—C14'—C15'—C16'	1.3 (3)
S1—C14—C15—C16	179.55 (15)	S1'—C14'—C15'—C16'	−176.87 (14)
C14—C15—C16—C17	0.5 (3)	C14'—C15'—C16'—C17'	1.3 (3)
C15—C16—C17—C18	−1.1 (3)	C15'—C16'—C17'—C18'	−1.6 (3)
C15—C16—C17—C20	177.26 (18)	C15'—C16'—C17'—C20'	−178.99 (17)
C16—C17—C18—C19	1.5 (3)	C16'—C17'—C18'—C19'	−0.8 (3)
C20—C17—C18—C19	−176.93 (17)	C20'—C17'—C18'—C19'	176.64 (17)
C15—C14—C19—C18	0.5 (3)	C17'—C18'—C19'—C14'	3.4 (3)
S1—C14—C19—C18	−179.24 (14)	C15'—C14'—C19'—C18'	−3.6 (3)
C17—C18—C19—C14	−1.1 (3)	S1'—C14'—C19'—C18'	174.55 (14)
C2—S2—C21—C22	−62.79 (16)	C2'—S2'—C21'—C22'	−69.37 (15)
S2—C21—C22—C23	139.26 (17)	S2'—C21'—C22'—C23'	143.09 (16)
S2—C21—C22—C27	−42.1 (2)	S2'—C21'—C22'—C27'	−39.4 (2)
C27—C22—C23—C24	−0.7 (3)	C27'—C22'—C23'—C24'	−0.6 (3)
C21—C22—C23—C24	177.92 (19)	C21'—C22'—C23'—C24'	176.99 (18)
C22—C23—C24—C25	1.3 (3)	C22'—C23'—C24'—C25'	1.1 (3)
C23—C24—C25—C26	−0.8 (3)	C23'—C24'—C25'—C26'	−0.8 (3)
C24—C25—C26—C27	−0.1 (3)	C24'—C25'—C26'—C27'	0.1 (3)
C25—C26—C27—C22	0.6 (3)	C25'—C26'—C27'—C22'	0.4 (3)
C23—C22—C27—C26	−0.2 (3)	C23'—C22'—C27'—C26'	−0.2 (3)
C21—C22—C27—C26	−178.82 (18)	C21'—C22'—C27'—C26'	−177.65 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H05···N4i	0.79 (3)	2.22 (3)	3.003 (2)	178 (3)
N5'—H05'···N4'i	0.82 (3)	2.23 (3)	3.048 (2)	171 (2)
C21—H21B···O2'ii	0.99	2.32	3.249 (2)	155
C21'—H21D···O2iii	0.99	2.23	3.145 (2)	154
C19—H19···O3iv	0.95	2.50	3.352 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H05⋯N4i	0.79 (3)	2.22 (3)	3.003 (2)	178 (3)
N5′—H05′⋯N4′i	0.82 (3)	2.23 (3)	3.048 (2)	171 (2)
C21—H21B⋯O2′ii	0.99	2.32	3.249 (2)	155
C21′—H21D⋯O2iii	0.99	2.23	3.145 (2)	154
C19—H19⋯O3iv	0.95	2.50	3.352 (2)	150

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