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Acta Cryst. (2008). E64, o2096    [ doi:10.1107/S1600536808032108 ]

N-[4-Acetyl-5-(3-methoxyphenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide

G. Aridoss, S. Amirthaganesan, D. Velmurugan, S. H. Kim and Y. T. Jeong

Abstract top

The title compound, C13H15N3O3S, crystallizes with two molecules in the asymmetric unit. The thiadiazole rings in both the molecules adopt an envelope conformation. The crystal packing is stabilized by intermolecular N-H...O and C-H...O interactions.

Comment top

Nitrogen heterocycles are one of the most important classes of biologically active compounds. Suitably substituted 1,3,4-thiadiazoles have attracted great attention owing to their broad spectrum of biological activities in the areas of medicine which includes antimicrobial, antituberculosis, anesthetic, antithrombotic, anticonvulsant, antihypertensive, anti-inflammatory and antiulcer activities (Balasubramanian et al., 2004; Li et al., 2001; Radwan et al. 2007; Supuran et al., 2001). Their action depends directly on the type and location of polar substituents on the heterocyclic ring. In general, pharmacological effect of potential drugs depends sensitively and solely on the stereochemistry and ring conformations. Thus, by keeping in view the promising biological potency of 1,3,4-thiadiazoles and variously substituted 1,3,4-thiadiazole frameworks, we have carried out the crystal structure determination of the title compound.

The title compound crystallizes with two molecules in the asymmetric unit. The sum of the angles at N1 (359.9 (6)°) and N4 (360.0 (6)°) are in accordance with sp2 hybridization. The torsion angles around C6—C1—O1—C13 [0.0 (4)°] and C19—C14—O4—C26 [-1.8 (4)°] indicates the coplanarity of the methoxy groups with the corresponding phenyl rings (C1–C6) and (C14–C19), respectively. The thiadiazole ring in both the molecules adopt envelope conformation with atoms C7 and C20 deviating by 0.395 (3) and 0.350 (3) Å, respectively, from the mean plane of the remaining atoms. The puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) for the thiadiazole rings C10—S2—C7—N1—N2 and C20—S2—C23—N5—N4 are q2 = 0.245 (2), 0.217 (2) Å, φ = 36.4 (6), 215.4 (6)° and Δs(C7) = 6.9 (2), Δs(C20) = 5.4 (2), respectively. N—H···O and C—H···O intermolecular interactions stabilize the crystal packing (Table 1).

Related literature top

For biological activities of thiadiazole derivatives, see: Balasubramanian et al. (2004); Li et al. (2001); Radwan et al. (2007); Supuran et al. (2001). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

The title compound was obtained by applying the method of Balasubramanian et al. (2004). 3-Methoxybenzadehyde thiosemicarbazone obtained by the reaction of 3-Methoxybenzadehyde and thiosemicarbazide was refluxed with excess of freshly distilled acetic anhydride on a water bath for about 7 h. After the completion of reaction, the excess of acetic anhydride was distilled off under reduced pressure and the obtained crude mass was purified by column chromatography (benzene–ethylacetate 5:1 v/v). Crystals were obtained from the solution of freshly distilled ethanol by slow evaporation at room temperature. 1H NMR (DMSO-d6, p.p.m.): 10.90 (s, 1H, amide NH); 7.36–6.76 (m, 5H, aromatic and ring methine protons); 3.78 (s, 3H, OCH3); 2.38 (s, 3H, –COCH3); 2.28 (s, 3H, –COCH3).

Refinement top

All H-atoms were refined using a riding model with d(C—H) = 0.93 Å, Uiso = 1.2Ueq (C) for aromatic, 0.98 Å, Uiso = 1.2Ueq (C) for CH, 0.96 Å, Uiso = 1.5Ueq (C) for CH3 and 0.86 Å, Uiso = 1.2Ueq (N) for NH atoms. The methyl groups were allowed to rotate but not to tip.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004) and SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004) and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. The molecular packing of the title compound. For clarity, hydrogen atoms which are not involved in hydrogen bonding were omitted.
N-[4-Acetyl-5-(3-methoxyphenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide top
Crystal data top
C13H15N3O3SF(000) = 616
Mr = 293.34Dx = 1.422 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 5353 reflections
a = 11.3790 (4) Åθ = 1.8–29.6°
b = 10.5993 (3) ŵ = 0.25 mm−1
c = 11.9596 (2) ÅT = 293 K
β = 108.225 (2)°Prism, colourless
V = 1370.08 (7) Å30.30 × 0.20 × 0.16 mm
Z = 4
Data collection top
Bruker Kappa-APEXII CCD
diffractometer		7595 independent reflections
Radiation source: fine-focus sealed tube5635 reflections with I > 2σ(I)
graphiteRint = 0.030
ω and φ scansθmax = 29.6°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)		h = −15→15
Tmin = 0.930, Tmax = 0.962k = −14→14
16660 measured reflectionsl = −14→16
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.109 w = 1/[σ2(Fo2) + (0.0466P)2 + 0.2666P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
7595 reflectionsΔρmax = 0.33 e Å−3
367 parametersΔρmin = −0.25 e Å−3
1 restraintAbsolute structure: Flack (1983), with 3584 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.07 (7)
Crystal data top
C13H15N3O3SV = 1370.08 (7) Å3
Mr = 293.34Z = 4
Monoclinic, P21Mo Kα radiation
a = 11.3790 (4) ŵ = 0.25 mm−1
b = 10.5993 (3) ÅT = 293 K
c = 11.9596 (2) Å0.30 × 0.20 × 0.16 mm
β = 108.225 (2)°
Data collection top
Bruker Kappa-APEXII CCD
diffractometer		7595 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)		5635 reflections with I > 2σ(I)
Tmin = 0.930, Tmax = 0.962Rint = 0.030
16660 measured reflectionsθmax = 29.6°
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.109Δρmax = 0.33 e Å−3
S = 1.03Δρmin = −0.25 e Å−3
7595 reflectionsAbsolute structure: Flack (1983), with 3584 Friedel pairs
367 parametersFlack parameter: 0.07 (7)
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
xyzUiso*/Ueq
C10.5869 (2)0.7772 (2)0.4618 (2)0.0397 (5)
C20.6405 (3)0.8511 (3)0.3955 (3)0.0498 (8)
H20.60270.85950.31480.060*
C30.7499 (3)0.9119 (3)0.4499 (2)0.0538 (7)
H30.78620.96150.40550.065*
C40.8069 (2)0.9005 (3)0.5697 (2)0.0442 (6)
H40.88080.94280.60550.053*
C50.7547 (2)0.8268 (2)0.6360 (2)0.0309 (5)
C60.64253 (18)0.7665 (2)0.5812 (2)0.0350 (5)
H60.60510.71860.62580.042*
C70.8123 (2)0.8112 (3)0.7677 (2)0.0324 (6)
H70.75460.84190.80760.039*
C80.9343 (2)1.0017 (3)0.8382 (2)0.0363 (6)
C91.0571 (2)1.0645 (3)0.8708 (3)0.0441 (7)
H9A1.04641.15410.87420.066*
H9B1.09691.04550.81290.066*
H9C1.10741.03460.94640.066*
C101.0096 (2)0.6892 (3)0.8300 (2)0.0315 (6)
C111.0879 (3)0.4753 (3)0.8707 (2)0.0390 (6)
C121.1970 (3)0.3942 (3)0.8773 (3)0.0569 (8)
H12A1.19200.36580.79970.085*
H12B1.19750.32260.92670.085*
H12C1.27160.44200.90980.085*
C130.4198 (2)0.6425 (3)0.4616 (3)0.0548 (7)
H13A0.39710.69250.51860.082*
H13B0.47480.57630.50110.082*
H13C0.34680.60620.40740.082*
C140.8900 (2)0.2827 (3)0.5333 (2)0.0431 (6)
C150.8399 (3)0.3437 (3)0.6089 (3)0.0499 (8)
H150.87340.33190.68970.060*
C160.7400 (3)0.4223 (3)0.5648 (2)0.0524 (7)
H160.70530.46230.61620.063*
C170.6906 (2)0.4425 (2)0.4454 (2)0.0420 (6)
H170.62360.49670.41640.050*
C180.7410 (2)0.3820 (3)0.3691 (2)0.0313 (5)
C190.84171 (19)0.3018 (2)0.4136 (2)0.0365 (5)
H190.87640.26110.36260.044*
C200.6864 (2)0.3966 (3)0.2384 (2)0.0316 (5)
H200.74590.36620.20050.038*
C210.5698 (2)0.2018 (3)0.1704 (2)0.0352 (6)
C220.4489 (2)0.1337 (3)0.1313 (3)0.0457 (7)
H22A0.42800.10560.19900.069*
H22B0.45540.06210.08440.069*
H22C0.38570.18950.08550.069*
C230.4851 (2)0.5119 (3)0.1630 (2)0.0307 (5)
C240.4060 (2)0.7251 (3)0.1174 (2)0.0371 (6)
C250.2952 (2)0.8055 (3)0.1067 (3)0.0520 (8)
H25A0.26160.83470.02710.078*
H25B0.31900.87660.15870.078*
H25C0.23400.75690.12750.078*
C261.0400 (3)0.1360 (3)0.5113 (3)0.0692 (9)
H26A1.07530.19350.46860.104*
H26B0.97720.08630.45680.104*
H26C1.10350.08140.55860.104*
N10.92957 (17)0.8777 (2)0.81336 (18)0.0319 (5)
N21.03611 (17)0.8057 (2)0.8278 (2)0.0339 (5)
N31.10017 (18)0.5994 (2)0.8432 (2)0.0383 (5)
H3A1.16890.62240.83360.046*
N40.57049 (17)0.3249 (2)0.1927 (2)0.0332 (5)
N50.46128 (17)0.3956 (2)0.16790 (19)0.0330 (5)
N60.39184 (18)0.6002 (2)0.1401 (2)0.0357 (5)
H6A0.31990.57540.13990.043*
O10.47967 (16)0.7197 (2)0.39944 (16)0.0550 (5)
O20.83930 (16)1.0588 (2)0.8297 (2)0.0525 (5)
O30.99404 (17)0.4378 (2)0.88764 (19)0.0514 (5)
O40.98715 (18)0.2046 (2)0.58456 (19)0.0676 (6)
O50.66898 (16)0.1464 (2)0.18601 (19)0.0513 (5)
O60.50089 (16)0.7653 (2)0.10697 (18)0.0487 (5)
S10.85560 (5)0.64828 (6)0.81229 (6)0.03785 (17)
S20.63984 (5)0.55696 (6)0.18841 (6)0.03857 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0346 (10)0.0384 (13)0.0415 (13)0.0002 (9)0.0053 (10)−0.0048 (10)
C20.0547 (16)0.054 (2)0.0347 (15)−0.0045 (14)0.0053 (13)0.0004 (13)
C30.0597 (15)0.0617 (19)0.0407 (15)−0.0191 (14)0.0166 (12)0.0057 (13)
C40.0404 (12)0.0500 (15)0.0426 (14)−0.0140 (11)0.0136 (11)−0.0016 (12)
C50.0285 (10)0.0297 (14)0.0349 (13)0.0004 (9)0.0102 (10)−0.0034 (11)
C60.0299 (9)0.0337 (12)0.0405 (12)−0.0024 (8)0.0099 (9)−0.0001 (10)
C70.0236 (10)0.0341 (14)0.0378 (14)−0.0022 (10)0.0071 (10)−0.0053 (12)
C80.0347 (12)0.0371 (16)0.0382 (15)0.0007 (11)0.0129 (11)−0.0028 (12)
C90.0377 (12)0.0392 (16)0.0552 (18)−0.0079 (13)0.0142 (12)−0.0115 (15)
C100.0253 (10)0.0370 (16)0.0324 (13)−0.0024 (10)0.0093 (9)−0.0015 (11)
C110.0412 (13)0.0371 (16)0.0370 (15)−0.0039 (12)0.0096 (11)−0.0004 (12)
C120.0521 (16)0.0326 (16)0.086 (2)0.0014 (14)0.0209 (16)0.0069 (17)
C130.0384 (12)0.0568 (17)0.0667 (18)−0.0103 (12)0.0129 (12)−0.0108 (15)
C140.0331 (10)0.0456 (15)0.0455 (14)−0.0001 (10)0.0048 (10)0.0045 (11)
C150.0554 (16)0.055 (2)0.0351 (16)−0.0062 (14)0.0080 (13)−0.0022 (13)
C160.0600 (15)0.0552 (18)0.0441 (15)0.0019 (13)0.0192 (13)−0.0117 (13)
C170.0406 (11)0.0386 (13)0.0458 (14)0.0050 (10)0.0119 (11)−0.0053 (11)
C180.0251 (10)0.0291 (14)0.0374 (14)−0.0036 (9)0.0066 (10)−0.0007 (11)
C190.0301 (9)0.0380 (12)0.0417 (13)0.0036 (9)0.0118 (9)0.0018 (11)
C200.0237 (10)0.0339 (14)0.0383 (14)−0.0015 (10)0.0112 (10)−0.0012 (12)
C210.0325 (12)0.0351 (15)0.0398 (15)−0.0032 (11)0.0141 (10)−0.0071 (12)
C220.0401 (13)0.0432 (18)0.0551 (18)−0.0099 (13)0.0167 (12)−0.0118 (15)
C230.0268 (10)0.0343 (15)0.0289 (13)−0.0005 (10)0.0056 (9)0.0035 (10)
C240.0371 (13)0.0330 (15)0.0358 (14)−0.0013 (11)0.0036 (11)0.0008 (12)
C250.0428 (14)0.0347 (16)0.074 (2)0.0065 (12)0.0111 (14)0.0046 (16)
C260.0557 (16)0.066 (2)0.088 (2)0.0258 (16)0.0253 (16)0.0328 (19)
N10.0219 (9)0.0343 (13)0.0381 (12)−0.0010 (8)0.0074 (8)−0.0054 (10)
N20.0238 (9)0.0348 (13)0.0425 (13)0.0014 (9)0.0096 (9)−0.0019 (10)
N30.0308 (10)0.0327 (13)0.0541 (14)−0.0009 (8)0.0171 (9)0.0045 (10)
N40.0234 (9)0.0334 (13)0.0407 (13)−0.0005 (9)0.0069 (8)−0.0048 (10)
N50.0257 (9)0.0332 (13)0.0388 (12)0.0007 (9)0.0083 (8)−0.0038 (10)
N60.0272 (9)0.0322 (13)0.0461 (12)−0.0002 (8)0.0089 (8)0.0034 (10)
O10.0433 (9)0.0665 (13)0.0459 (10)−0.0145 (9)0.0006 (8)−0.0070 (10)
O20.0383 (9)0.0388 (12)0.0845 (15)0.0039 (10)0.0252 (10)−0.0079 (12)
O30.0465 (11)0.0472 (14)0.0617 (13)−0.0102 (10)0.0187 (10)0.0077 (11)
O40.0572 (11)0.0840 (16)0.0567 (12)0.0303 (11)0.0110 (10)0.0231 (12)
O50.0363 (9)0.0405 (12)0.0795 (14)0.0048 (10)0.0216 (9)−0.0079 (12)
O60.0431 (10)0.0430 (13)0.0617 (13)−0.0049 (9)0.0187 (9)0.0097 (11)
S10.0281 (3)0.0403 (4)0.0434 (4)−0.0051 (3)0.0087 (2)0.0057 (3)
S20.0264 (3)0.0371 (4)0.0505 (4)−0.0023 (3)0.0096 (3)0.0090 (3)
Geometric parameters (Å, °) top
C1—O11.359 (3)C14—C191.377 (3)
C1—C61.374 (3)C15—C161.374 (4)
C1—C21.384 (4)C15—H150.9300
C2—C31.372 (4)C16—C171.378 (4)
C2—H20.9300C16—H160.9300
C3—C41.380 (4)C17—C181.378 (3)
C3—H30.9300C17—H170.9300
C4—C51.374 (3)C18—C191.392 (3)
C4—H40.9300C18—C201.499 (3)
C5—C61.394 (3)C19—H190.9300
C5—C71.514 (4)C20—N41.471 (3)
C6—H60.9300C20—S21.824 (3)
C7—N11.456 (3)C20—H200.9800
C7—S11.829 (3)C21—O51.234 (3)
C7—H70.9800C21—N41.332 (4)
C8—O21.215 (3)C21—C221.493 (3)
C8—N11.345 (4)C22—H22A0.9600
C8—C91.486 (4)C22—H22B0.9600
C9—H9A0.9600C22—H22C0.9600
C9—H9B0.9600C23—N51.267 (4)
C9—H9C0.9600C23—N61.377 (3)
C10—N21.274 (3)C23—S21.757 (2)
C10—N31.375 (3)C24—N61.370 (4)
C10—S11.753 (2)C24—C251.493 (4)
C11—O31.215 (3)C25—H25A0.9600
C11—N31.373 (4)C25—H25B0.9600
C11—C121.492 (4)C25—H25C0.9600
C12—H12A0.9600C26—O41.410 (4)
C12—H12B0.9600C26—H26A0.9600
C12—H12C0.9600C26—H26B0.9600
C13—O11.416 (3)C26—H26C0.9600
C13—H13A0.9600N1—N21.397 (3)
C13—H13B0.9600N3—H3A0.8600
C13—H13C0.9600N4—N51.401 (3)
C14—O41.364 (3)N6—H6A0.8600
C14—C151.373 (4)
O1—C1—C6125.1 (2)C16—C17—C18119.6 (2)
O1—C1—C2114.9 (2)C16—C17—H17120.2
C6—C1—C2120.0 (2)C18—C17—H17120.2
C3—C2—C1119.4 (3)C17—C18—C19119.6 (2)
C3—C2—H2120.3C17—C18—C20121.3 (2)
C1—C2—H2120.3C19—C18—C20119.0 (2)
C2—C3—C4120.9 (3)C14—C19—C18120.0 (2)
C2—C3—H3119.6C14—C19—H19120.0
C4—C3—H3119.6C18—C19—H19120.0
C5—C4—C3120.1 (2)N4—C20—C18111.4 (2)
C5—C4—H4120.0N4—C20—S2103.01 (16)
C3—C4—H4120.0C18—C20—S2114.9 (2)
C4—C5—C6119.2 (2)N4—C20—H20109.1
C4—C5—C7122.5 (2)C18—C20—H20109.1
C6—C5—C7118.3 (2)S2—C20—H20109.1
C1—C6—C5120.5 (2)O5—C21—N4119.2 (2)
C1—C6—H6119.8O5—C21—C22121.8 (3)
C5—C6—H6119.8N4—C21—C22118.9 (2)
N1—C7—C5112.6 (2)C21—C22—H22A109.5
N1—C7—S1102.46 (16)C21—C22—H22B109.5
C5—C7—S1113.33 (19)H22A—C22—H22B109.5
N1—C7—H7109.4C21—C22—H22C109.5
C5—C7—H7109.4H22A—C22—H22C109.5
S1—C7—H7109.4H22B—C22—H22C109.5
O2—C8—N1119.7 (3)N5—C23—N6120.6 (2)
O2—C8—C9122.5 (3)N5—C23—S2118.25 (19)
N1—C8—C9117.7 (2)N6—C23—S2121.2 (2)
C8—C9—H9A109.5O6—C24—N6121.8 (3)
C8—C9—H9B109.5O6—C24—C25123.3 (3)
H9A—C9—H9B109.5N6—C24—C25114.9 (2)
C8—C9—H9C109.5C24—C25—H25A109.5
H9A—C9—H9C109.5C24—C25—H25B109.5
H9B—C9—H9C109.5H25A—C25—H25B109.5
N2—C10—N3120.0 (2)C24—C25—H25C109.5
N2—C10—S1118.12 (19)H25A—C25—H25C109.5
N3—C10—S1121.8 (2)H25B—C25—H25C109.5
O3—C11—N3120.9 (3)O4—C26—H26A109.5
O3—C11—C12124.3 (3)O4—C26—H26B109.5
N3—C11—C12114.8 (3)H26A—C26—H26B109.5
C11—C12—H12A109.5O4—C26—H26C109.5
C11—C12—H12B109.5H26A—C26—H26C109.5
H12A—C12—H12B109.5H26B—C26—H26C109.5
C11—C12—H12C109.5C8—N1—N2122.2 (2)
H12A—C12—H12C109.5C8—N1—C7121.6 (2)
H12B—C12—H12C109.5N2—N1—C7116.1 (2)
O1—C13—H13A109.5C10—N2—N1109.3 (2)
O1—C13—H13B109.5C11—N3—C10124.2 (2)
H13A—C13—H13B109.5C11—N3—H3A117.9
O1—C13—H13C109.5C10—N3—H3A117.9
H13A—C13—H13C109.5C21—N4—N5122.2 (2)
H13B—C13—H13C109.5C21—N4—C20122.0 (2)
O4—C14—C15115.8 (2)N5—N4—C20115.8 (2)
O4—C14—C19124.1 (2)C23—N5—N4110.0 (2)
C15—C14—C19120.2 (2)C24—N6—C23124.4 (2)
C14—C15—C16119.7 (3)C24—N6—H6A117.8
C14—C15—H15120.1C23—N6—H6A117.8
C16—C15—H15120.1C1—O1—C13117.9 (2)
C15—C16—C17120.9 (3)C14—O4—C26118.5 (2)
C15—C16—H16119.6C10—S1—C788.3 (1)
C17—C16—H16119.6C23—S2—C2088.6 (1)
O1—C1—C2—C3−179.1 (3)N3—C10—N2—N1179.8 (2)
C6—C1—C2—C30.8 (4)S1—C10—N2—N11.3 (3)
C1—C2—C3—C4−0.1 (5)C8—N1—N2—C10162.3 (3)
C2—C3—C4—C50.5 (5)C7—N1—N2—C10−18.8 (3)
C3—C4—C5—C6−1.4 (4)O3—C11—N3—C10−1.5 (4)
C3—C4—C5—C7−179.6 (3)C12—C11—N3—C10178.4 (3)
O1—C1—C6—C5178.2 (2)N2—C10—N3—C11166.0 (3)
C2—C1—C6—C5−1.8 (4)S1—C10—N3—C11−15.5 (4)
C4—C5—C6—C12.1 (4)O5—C21—N4—N5174.7 (2)
C7—C5—C6—C1−179.6 (2)C22—C21—N4—N5−7.5 (4)
C4—C5—C7—N1−2.5 (4)O5—C21—N4—C20−1.6 (4)
C6—C5—C7—N1179.3 (2)C22—C21—N4—C20176.2 (2)
C4—C5—C7—S1−118.2 (2)C18—C20—N4—C21−81.9 (3)
C6—C5—C7—S163.5 (3)S2—C20—N4—C21154.4 (2)
O4—C14—C15—C16−178.6 (3)C18—C20—N4—N5101.6 (3)
C19—C14—C15—C161.1 (4)S2—C20—N4—N5−22.2 (3)
C14—C15—C16—C17−1.1 (5)N6—C23—N5—N4−179.8 (2)
C15—C16—C17—C180.8 (4)S2—C23—N5—N4−0.8 (3)
C16—C17—C18—C19−0.4 (4)C21—N4—N5—C23−160.5 (3)
C16—C17—C18—C20177.1 (3)C20—N4—N5—C2316.0 (3)
O4—C14—C19—C18179.0 (2)O6—C24—N6—C235.9 (4)
C15—C14—C19—C18−0.7 (4)C25—C24—N6—C23−174.3 (2)
C17—C18—C19—C140.4 (4)N5—C23—N6—C24−170.8 (3)
C20—C18—C19—C14−177.2 (2)S2—C23—N6—C2410.3 (4)
C17—C18—C20—N4−74.4 (3)C6—C1—O1—C130.0 (4)
C19—C18—C20—N4103.1 (2)C2—C1—O1—C13180.0 (2)
C17—C18—C20—S242.2 (3)C15—C14—O4—C26177.9 (3)
C19—C18—C20—S2−140.2 (2)C19—C14—O4—C26−1.8 (4)
O2—C8—N1—N2−176.4 (2)N2—C10—S1—C711.6 (2)
C9—C8—N1—N26.0 (4)N3—C10—S1—C7−166.9 (2)
O2—C8—N1—C74.7 (4)N1—C7—S1—C10−18.96 (18)
C9—C8—N1—C7−172.9 (2)C5—C7—S1—C10102.70 (18)
C5—C7—N1—C882.3 (3)N5—C23—S2—C20−10.6 (2)
S1—C7—N1—C8−155.5 (2)N6—C23—S2—C20168.4 (2)
C5—C7—N1—N2−96.6 (3)N4—C20—S2—C2316.77 (18)
S1—C7—N1—N225.5 (3)C18—C20—S2—C23−104.62 (18)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O5i0.861.952.801 (3)171
N6—H6A···O2ii0.861.962.799 (3)164
C25—H25C···O2ii0.962.373.238 (4)150
Symmetry codes: (i) −x+2, y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O5i0.861.952.801 (3)171
N6—H6A···O2ii0.861.962.799 (3)164
C25—H25C···O2ii0.962.373.238 (4)150
Symmetry codes: (i) −x+2, y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1.
Acknowledgements top

GA and YTJ are grateful for the support provided by the second stage of the BK21 Program, Republic of Korea. DV acknowledges financial support from the University Grants Commission (UGC-SAP) and the Department of Science and Technology (DST-FIST), Government of India, for providing facilities.

references
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