(S)-N-[1-(5-Benzyl­sulfan­yl-1,3,4-oxa­diazol-2-yl)-2-phenyl­eth­yl]-4-methyl­benzene­sulfonamide

Syed, T.; Hameed, S.; Jones, P.G.

doi:10.1107/S1600536811040669

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages o2875-o2876

doi:10.1107/S1600536811040669

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(S)-N-[1-(5-Benzylsulfanyl-1,3,4-oxadiazol-2-yl)-2-phenylethyl]-4-methylbenzenesulfonamide

Tayyaba Syed,^a Shahid Hameed ^a ^* and Peter G. Jones ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bInstitut for Anorganische und Analytische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany
^*Correspondence e-mail: shameed@qau.edu.pk

(Received 23 September 2011; accepted 3 October 2011; online 8 October 2011)

The title compound, C₂₄H₂₃N₃O₃S₂, crystallizes with two independent molecules 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, molecules are connected by two classical N—H⋯N hydrogen bonds and two weak but very short C—H⋯O_sulfonyl interactions, 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_r = 465.57
Monoclinic, C 2
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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.031
wR(F²) = 0.080
S = 1.04
8447 reflections
587 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 3306 Friedel pairs
Flack parameter: 0.008 (9)

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⋯O3^iv	0.95	2.50	3.352 (2)	150
Symmetry codes: (i) x, y-1, z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+1]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z]$ ; (iv) x, y+1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811040669/su2319sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811040669/su2319Isup3.cml

checkCIF report

Comment top

The literature contains many reports of a variety of biological activities of substituted-1,3,4-oxadiazoles. These include anti-convulsant (Zarghi et al., 2005), anti-proliferative (Zahid et al., 2009), anti-tumour and anti-viral (Akhtar et al., 2008), anti-bacterial (Iqbal et al., 2006), urease inhibition (Akhtar et al., 2010), and anti-mitotic (Aboraia et al., 2006) activities. Some sulfonamide-bearing 1,3,4-oxadiazoles have also been reported in the literature to show anti-HIV (Syed et al., 2011a), and anti-microbial (Zareef et al., 2007) activities. The title compound was synthesized in our laboratory to explore its anti-HIV and anti-HCV activities and herein we report on its crystal structure.

The molecular structure of the two independent molecules (1 and 2) of the enantiomerically pure title compound are shown in Fig. 1. The two molecules are related by a pseudo twofold axis. The main difference between the two molecules is the rotation of the tolyl group; the corresponding torsion angles are N5—S1—C14—C15 61.4 (2), and N5'—S1'—C14'—C15' 100.2 (2)°. A least-squares fit of both molecules, ignoring atoms (C15–C20), gave an r.m.s. deviation of 0.19 Å (Fig. 2). The large number of single bonds means that the molecules have a considerable number of torsional degrees of freedom. The conformation actually adopted is a flattened form in which all rings are arranged to correspond approximately to the smallest dimension of the molecular "box". This was calculated, [RPLUTO; CCDC, 2007], to be 7.9Å for molecule 1 and 7.7 Å for molecule 2.

Within the asymmetric unit, significant contacts are the intramolecular C13-H13···Cg(C22–27) 2.91 Å, and the π···π stacking between rings (C14–C19) and (C14'–C19') with a centroid-centroid distance of 3.01 Å . The former necessitates a suitable orientation of the ring (C22–C27), associated with the torsion angle N3—C2—S2—C21 155.8 (2), and N3'—C2'—S2'—C2' 1154.3 (2)°. In the corresponding compound with a methyl instead of a phenylmethyl substituent at C6 (Syed et al., 2011b), this ring is rotated in the opposite direction, towards the tolyl group, with torsion angle N—C—S—C being -3.6 (2)°. There the π···π contact has an interplanar angle of 8.2 (1)° and a Cg···Cg distance of 3.75 Å; the ring offset was estimated to be ca 1.5 Å.

In the crystal of the title compound, the molecular packing is largely determined by two short classical N-H···N hydrogen bonds, together with two "weak" but very short C-H···O_sulfonyl interactions (see Table 1 for details). The combinaton of these interactions leads to the formation of layers lying parallel to the bc plane (Fig. 3).

Related literature top

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, 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 top

The synthesis and spectral data of the compound under study have been described previously by our laboratory (Syed et al., 2011a).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the numbering scheme for the two independent molecules (1 left; 2 right). Displacement ellipsoids are drawn at the 50% probability levels.
	Fig. 2. A least-squares fit of the two independent molecules (molecule 1 dotted lines). All non-H atoms were fitted except the ring atoms (C15–C20) on the left-hand side of the figure.
	Fig. 3. Crystal packing of the title compound, viewed perpendicular to the bc plane in the region x ≈ 7/8. Thick dashed lines represent classical and thin dashed lines "weak" hydrogen bonds. Hydrogen atoms not involved in these interactions have been omitted for clarity. The three vertical rows of molecules are composed of molecules 2, 1, 2, respectively.

(S)-N-[1-(5-Benzylsulfanyl-1,3,4-oxadiazol-2-yl)-2- phenylethyl]-4-methylbenzenesulfonamide top

Crystal data top

C₂₄H₂₃N₃O₃S₂	F(000) = 1952
M_r = 465.57	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0523P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
8447 reflections	Δρ_max = 0.27 e Å⁻³
587 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 3306 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.008 (9)

Crystal data top

C₂₄H₂₃N₃O₃S₂	V = 4464.5 (5) Å³
M_r = 465.57	Z = 8
Monoclinic, C2	Cu Kα radiation
a = 41.128 (2) Å	µ = 2.43 mm⁻¹
b = 5.7205 (5) Å	T = 100 K
c = 18.9783 (11) Å	0.25 × 0.08 × 0.03 mm
β = 90.940 (4)°

Data collection top

Oxford Diffraction Xcalibur Nova A diffractometer	8447 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	7718 reflections with I > 2σ(I)
T_min = 0.740, T_max = 1.000	R_int = 0.049
42976 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.080	Δρ_max = 0.27 e Å⁻³
S = 1.04	Δρ_min = −0.21 e Å⁻³
8447 reflections	Absolute structure: Flack (1983), 3306 Friedel pairs
587 parameters	Absolute structure parameter: 0.008 (9)
1 restraint

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O3^iv	0.95	2.50	3.352 (2)	150

Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, y−1/2, −z+1; (iii) −x+1/2, y−1/2, −z; (iv) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₃N₃O₃S₂
M_r	465.57
Crystal system, space group	Monoclinic, C2
Temperature (K)	100
a, b, c (Å)	41.128 (2), 5.7205 (5), 18.9783 (11)
β (°)	90.940 (4)
V (Å³)	4464.5 (5)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	2.43
Crystal size (mm)	0.25 × 0.08 × 0.03

Data collection
Diffractometer	Oxford Diffraction Xcalibur Nova A diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.740, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	42976, 8447, 7718
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.080, 1.04
No. of reflections	8447
No. of parameters	587
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.21
Absolute structure	Flack (1983), 3306 Friedel pairs
Absolute structure parameter	0.008 (9)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Siemens, 1994).

Hydrogen-bond geometry (Å, º) top

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···O3^iv	0.95	2.50	3.352 (2)	150

Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, y−1/2, −z+1; (iii) −x+1/2, y−1/2, −z; (iv) x, y+1, z.

References

Aboraia, A. S., Abdel-Rahman, H. M., Mahfouz, N. M. & EL-Gendy, M. A. (2006). Bioorg. Med. Chem. 14, 1236–1246. Web of Science CrossRef PubMed CAS Google Scholar
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CCDC (2007). RPLUTO. Cambridge Crystallographic Data Centre, Union Road, Cambridge, England. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Iqbal, R., Zareef, M., Ahmed, S., Zaidi, J. H., Khan, K. M., Arfan, M., Shafique, M. & Shahzad, S. A. (2006). J. Chem. Soc. Pak. 28, 165–168. CAS Google Scholar
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Syed, T., Akhtar, T., Al-Masoudi, N. A., Jones, P. G. & Hameed, S. (2011a). J. Enzym. Inhib. Med. Chem. 26, doi:10.3109/14756366.2010.546792. Web of Science CrossRef Google Scholar
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Zahid, M., Yasin, K. A., Akhtar, T., Rama, N. H., Hameed, S., Al-Masoudi, N. A., Loddo, R. & La Colla, P. (2009). ARKIVOC, xi, 85–93. CrossRef Google Scholar
Zareef, M., Iqbal, R., Al-Masoudi, N. A., Zaidi, J. H., Arfan, M. & Shahzad, S. A. (2007). Phosphorus Sulfur Silicon Relat. Elem. 182, 281–298. Web of Science CrossRef CAS Google Scholar
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Volume 67| Part 11| November 2011| Pages o2875-o2876

doi:10.1107/S1600536811040669

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(S)-N-[1-(5-Benzyl­sulfan­yl-1,3,4-oxa­diazol-2-yl)-2-phenyl­eth­yl]-4-methyl­benzene­sulfonamide

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Experimental

Crystal data

Data collection

Refinement

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organic compounds

(S)-N-[1-(5-Benzylsulfanyl-1,3,4-oxadiazol-2-yl)-2-phenylethyl]-4-methylbenzenesulfonamide