Literature DB >> 24427045

3-Benzhydryl-1,3,4-thia-diazole-2(3H)-thione.

Megan T Thornton1, Peter C Healy2, Luke C Henderson1.   

Abstract

In the title compound, C15H12N2S2, the two phenyl rings and the planar (r.m.s. deviation = 0.002 Å) thia-diazole ring adopt a propeller conformation about the central C-H axis with H-C-C-C(phen-yl) torsion angles of 44 and 42° and an H-C-N-C(thia-diazole) torsion angle of 28°. Intra-molecular C-H⋯S and C-H⋯N contacts are observed. In the crystal, centrosymmetrically related mol-ecules associate through C-H⋯π inter-actions. These are connected into a supra-molecular chain along [101] by C-H⋯N inter-actions.

Entities:  

Year:  2013        PMID： 24427045      PMCID： PMC3884419          DOI： 10.1107/S1600536813021867

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For details of the use of 1,3,4-thia­diazo­les in the synthesis of crown ethers, see: Pappalardo et al. (1987 ▶). For their uses as scaffolds in potential pharmaceuticals, see; Aggarwal et al. (2012 ▶); Bhole & Bhusari (2011 ▶); Ghani & Ullah (2010 ▶); Kadi et al. (2010 ▶); Zhan et al. (2009 ▶).

Experimental

Crystal data

C15H12N2S2 M = 284.41 Monoclinic, a = 9.1198 (4) Å b = 15.4226 (5) Å c = 10.7584 (4) Å β = 108.546 (5)° V = 1434.60 (10) Å3 Z = 4 Mo Kα radiation μ = 0.36 mm−1 T = 223 K 0.44 × 0.29 × 0.18 mm

Data collection

Oxford-Diffraction GEMINI S Ultra diffractometer Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.859, T max = 0.938 5244 measured reflections 2524 independent reflections 2144 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.108 S = 1.13 2524 reflections 172 parameters H-atom parameters constrained Δρmax = 0.24 e Å−3 Δρmin = −0.53 e Å−3 Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: TEXSAN (Molecular Structure Corporation, 2001 ▶) and SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: TEXSAN and SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813021867/tk5245sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021867/tk5245Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813021867/tk5245Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H12N2S2F(000) = 592
Mr = 284.41Dx = 1.317 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ynCell parameters from 2095 reflections
a = 9.1198 (4) Åθ = 3.3–30.4°
b = 15.4226 (5) ŵ = 0.36 mm−1
c = 10.7584 (4) ÅT = 223 K
β = 108.546 (5)°Block, colourless
V = 1434.60 (10) Å30.44 × 0.29 × 0.18 mm
Z = 4
Oxford-Diffraction GEMINI S Ultra diffractometer2524 independent reflections
Radiation source: Enhance (Mo) X-ray Source2144 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 16.0774 pixels mm-1θmax = 25.0°, θmin = 3.3°
ω and φ scansh = −9→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)k = −15→18
Tmin = 0.859, Tmax = 0.938l = −12→8
5244 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.13w = 1/[σ2(Fo2) + (0.0518P)2 + 0.4906P] where P = (Fo2 + 2Fc2)/3
2524 reflections(Δ/σ)max = 0.001
172 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.53 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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.
xyzUiso*/Ueq
S10.14225 (8)0.60316 (4)0.93721 (6)0.0449 (2)
S2−0.07408 (7)0.55846 (4)0.66718 (7)0.0443 (2)
N30.18984 (19)0.47793 (10)0.80719 (16)0.0252 (5)
N40.3130 (2)0.47539 (12)0.92075 (18)0.0356 (6)
C10.1813 (2)0.41149 (13)0.70617 (19)0.0243 (6)
C20.0829 (2)0.54127 (13)0.7940 (2)0.0286 (7)
C50.3017 (3)0.53775 (16)0.9967 (2)0.0413 (8)
C110.0918 (2)0.33159 (13)0.7227 (2)0.0258 (6)
C120.0312 (3)0.27892 (15)0.6142 (2)0.0389 (8)
C13−0.0465 (3)0.20345 (16)0.6232 (3)0.0495 (9)
C14−0.0660 (3)0.18047 (15)0.7410 (3)0.0500 (9)
C15−0.0069 (3)0.23250 (17)0.8493 (3)0.0463 (9)
C160.0723 (3)0.30800 (15)0.8406 (2)0.0358 (7)
C210.3436 (2)0.39221 (12)0.70245 (19)0.0238 (6)
C220.4181 (3)0.45525 (14)0.6523 (2)0.0312 (7)
C230.5672 (3)0.44091 (15)0.6484 (2)0.0361 (7)
C240.6424 (3)0.36380 (16)0.6942 (2)0.0365 (8)
C250.5692 (3)0.30087 (14)0.7442 (2)0.0363 (7)
C260.4200 (2)0.31507 (13)0.7485 (2)0.0307 (7)
H10.125700.436500.624000.0290*
H50.376500.547001.080200.0500*
H120.043100.294900.532600.0470*
H13−0.086400.167400.548400.0590*
H14−0.120000.128900.747300.0600*
H15−0.020400.216700.930300.0560*
H160.113200.343600.915800.0430*
H220.367000.508300.620500.0370*
H230.617600.484300.614100.0430*
H240.744100.354200.691300.0440*
H250.620600.247800.775600.0440*
H260.370100.271600.783300.0370*
U11U22U33U12U13U23
S10.0499 (4)0.0387 (4)0.0422 (4)0.0092 (3)0.0090 (3)−0.0159 (3)
S20.0313 (3)0.0448 (4)0.0473 (4)0.0123 (3)−0.0008 (3)−0.0057 (3)
N30.0253 (9)0.0241 (9)0.0232 (9)0.0009 (7)0.0035 (7)−0.0041 (7)
N40.0382 (11)0.0352 (10)0.0241 (10)0.0063 (8)−0.0033 (8)−0.0048 (8)
C10.0250 (10)0.0234 (10)0.0218 (10)0.0005 (8)0.0036 (8)−0.0037 (8)
C20.0291 (11)0.0247 (11)0.0327 (12)0.0003 (8)0.0109 (10)−0.0023 (9)
C50.0474 (15)0.0391 (13)0.0294 (13)0.0047 (11)0.0009 (11)−0.0089 (10)
C110.0200 (10)0.0256 (11)0.0305 (11)0.0015 (8)0.0063 (9)−0.0012 (8)
C120.0386 (13)0.0395 (13)0.0384 (13)−0.0091 (11)0.0119 (11)−0.0108 (11)
C130.0440 (15)0.0361 (14)0.0647 (18)−0.0127 (11)0.0120 (13)−0.0172 (13)
C140.0388 (14)0.0298 (13)0.081 (2)−0.0030 (11)0.0184 (14)0.0075 (13)
C150.0426 (15)0.0446 (15)0.0529 (16)0.0011 (11)0.0171 (13)0.0166 (12)
C160.0327 (12)0.0386 (13)0.0352 (13)−0.0014 (10)0.0094 (10)0.0007 (10)
C210.0246 (10)0.0249 (10)0.0197 (10)−0.0011 (8)0.0040 (8)−0.0044 (8)
C220.0337 (12)0.0317 (12)0.0267 (12)0.0004 (9)0.0076 (10)0.0053 (9)
C230.0338 (13)0.0442 (13)0.0314 (12)−0.0069 (10)0.0120 (10)0.0030 (10)
C240.0269 (12)0.0476 (14)0.0356 (13)−0.0003 (10)0.0108 (10)−0.0067 (11)
C250.0327 (12)0.0303 (12)0.0441 (14)0.0061 (10)0.0096 (10)−0.0025 (10)
C260.0289 (12)0.0259 (11)0.0377 (12)0.0000 (9)0.0110 (10)0.0003 (9)
S1—C21.746 (2)C22—C231.391 (4)
S1—C51.718 (3)C23—C241.383 (3)
S2—C21.655 (2)C24—C251.380 (4)
N3—N41.372 (3)C25—C261.393 (3)
N3—C11.478 (3)C1—H10.9500
N3—C21.356 (3)C5—H50.9500
N4—C51.287 (3)C12—H120.9500
C1—C111.519 (3)C13—H130.9500
C1—C211.523 (3)C14—H140.9500
C11—C121.385 (3)C15—H150.9500
C11—C161.384 (3)C16—H160.9500
C12—C131.382 (4)C22—H220.9500
C13—C141.381 (4)C23—H230.9500
C14—C151.376 (4)C24—H240.9500
C15—C161.389 (4)C25—H250.9500
C21—C221.390 (3)C26—H260.9500
C21—C261.388 (3)
S1···N42.552 (2)C23···H23vi3.0200
S2···C23i3.689 (3)C23···H5iv2.8100
S2···H12.7600C24···H5iv2.8400
S2···H23i2.9200C24···H15viii3.0200
S2···H25ii3.0400C25···H5iv2.9500
S2···H1iii3.0200C26···H5iv3.0300
S2···H12iii3.1900H1···S22.7600
N3···S12.5023 (17)H1···H122.4200
N4···C223.334 (3)H1···H222.4700
N4···S12.552 (2)H1···S2iii3.0200
N4···C163.320 (3)H5···N4iv2.8600
N4···C5iv3.345 (3)H5···C21iv3.0100
N4···C263.413 (3)H5···C22iv2.8900
N3···H162.5800H5···C23iv2.8100
N4···H162.7200H5···C24iv2.8400
N4···H5iv2.8600H5···C25iv2.9500
N4···H13v2.6000H5···C26iv3.0300
C5···N4iv3.345 (3)H12···H12.4200
C5···C24iv3.542 (3)H12···S2iii3.1900
C12···C263.422 (3)H13···N4ix2.6000
C16···N43.320 (3)H14···C23x3.0900
C22···N43.334 (3)H15···C24xi3.0200
C23···C23vi3.540 (3)H16···N32.5800
C23···S2vii3.689 (3)H16···N42.7200
C24···C5iv3.542 (3)H22···H12.4700
C26···C123.422 (3)H22···H23vi2.5700
C26···N43.413 (3)H23···S2vii2.9200
C11···H262.5800H23···C22vi2.9300
C11···H24i3.1000H23···C23vi3.0200
C12···H263.0500H23···H22vi2.5700
C15···H24i3.0200H24···C11vii3.1000
C16···H263.0200H24···C15vii3.0200
C16···H24i3.0000H24···C16vii3.0000
C21···H5iv3.0100H25···S2x3.0400
C22···H23vi2.9300H26···C112.5800
C22···H5iv2.8900H26···C123.0500
C23···H14ii3.0900H26···C163.0200
C2—S1—C589.76 (10)C21—C26—C25120.50 (19)
N4—N3—C1118.15 (16)N3—C1—H1107.00
N4—N3—C2118.15 (16)C11—C1—H1107.00
C1—N3—C2123.70 (17)C21—C1—H1107.00
N3—N4—C5109.62 (19)S1—C5—H5122.00
N3—C1—C11112.39 (16)N4—C5—H5122.00
N3—C1—C21109.30 (16)C11—C12—H12120.00
C11—C1—C21114.05 (16)C13—C12—H12120.00
S1—C2—S2125.74 (12)C12—C13—H13120.00
S1—C2—N3106.91 (14)C14—C13—H13120.00
S2—C2—N3127.35 (16)C13—C14—H14120.00
S1—C5—N4115.57 (17)C15—C14—H14120.00
C1—C11—C12117.54 (18)C14—C15—H15120.00
C1—C11—C16123.42 (19)C16—C15—H15120.00
C12—C11—C16119.0 (2)C11—C16—H16120.00
C11—C12—C13120.7 (2)C15—C16—H16120.00
C12—C13—C14119.9 (2)C21—C22—H22120.00
C13—C14—C15119.8 (2)C23—C22—H22120.00
C14—C15—C16120.3 (3)C22—C23—H23120.00
C11—C16—C15120.2 (2)C24—C23—H23120.00
C1—C21—C22118.23 (18)C23—C24—H24120.00
C1—C21—C26122.67 (17)C25—C24—H24120.00
C22—C21—C26119.10 (19)C24—C25—H25120.00
C21—C22—C23120.2 (2)C26—C25—H25120.00
C22—C23—C24120.3 (2)C21—C26—H26120.00
C23—C24—C25119.8 (3)C25—C26—H26120.00
C24—C25—C26120.1 (2)
C5—S1—C2—S2−179.44 (16)C21—C1—C11—C12−76.1 (2)
C5—S1—C2—N30.18 (16)C21—C1—C11—C16101.9 (2)
C2—S1—C5—N4−0.3 (2)N3—C1—C21—C26108.4 (2)
C1—N3—N4—C5179.84 (19)C1—C11—C12—C13177.6 (2)
N4—N3—C1—C1190.8 (2)C12—C11—C16—C150.1 (4)
N4—N3—C1—C21−36.9 (2)C16—C11—C12—C13−0.6 (4)
C2—N3—N4—C5−0.1 (3)C1—C11—C16—C15−178.0 (2)
C2—N3—C1—C21143.07 (18)C11—C12—C13—C140.8 (4)
N4—N3—C2—S1−0.1 (2)C12—C13—C14—C15−0.5 (4)
N4—N3—C2—S2179.55 (16)C13—C14—C15—C160.0 (4)
C1—N3—C2—S1179.96 (14)C14—C15—C16—C110.3 (4)
C1—N3—C2—S2−0.4 (3)C1—C21—C22—C23179.23 (18)
C2—N3—C1—C11−89.3 (2)C26—C21—C22—C230.1 (3)
N3—N4—C5—S10.3 (3)C1—C21—C26—C25−179.32 (18)
N3—C1—C11—C12158.78 (19)C22—C21—C26—C25−0.2 (3)
N3—C1—C11—C16−23.2 (3)C21—C22—C23—C240.1 (3)
C11—C1—C21—C22162.48 (18)C22—C23—C24—C25−0.1 (3)
C11—C1—C21—C26−18.4 (3)C23—C24—C25—C260.0 (3)
N3—C1—C21—C22−70.8 (2)C24—C25—C26—C210.2 (3)
D—H···AD—HH···AD···AD—H···A
C1—H1···S20.952.763.181 (2)108
C16—H16···N30.952.582.897 (3)100
C5—H5···Cg2iv0.952.743.670 (3)157
C13—H13···N4ix0.952.603.495 (3)157
Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C21–C26 phenyl ring.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C1—H1⋯S20.952.763.181 (2)108
C16—H16⋯N30.952.582.897 (3)100
C5—H5⋯Cg2i 0.952.743.670 (3)157
C13—H13⋯N4ii 0.952.603.495 (3)157

Symmetry codes: (i) ; (ii) .

  6 in total

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Authors:  Usman Ghani; Nisar Ullah
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2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Synthesis of novel nalidixic acid-based 1,3,4-thiadiazole and 1,3,4-oxadiazole derivatives as potent antibacterial agents.

Authors:  Nisha Aggarwal; Rajesh Kumar; Prem Dureja; Jitender Mohan Khurana
Journal:  Chem Biol Drug Des       Date:  2012-02-01       Impact factor: 2.817

4.  Synthesis, antimicrobial and anti-inflammatory activities of novel 5-(1-adamantyl)-1,3,4-thiadiazole derivatives.

Authors:  Adnan A Kadi; Ebtehal S Al-Abdullah; Ihsan A Shehata; Elsayed E Habib; Tarek M Ibrahim; Ali A El-Emam
Journal:  Eur J Med Chem       Date:  2010-08-12       Impact factor: 6.514

5.  Synthesis and anti-HIV activity evaluation of 2-(4-(naphthalen-2-yl)-1,2,3-thiadiazol-5-ylthio)-N-acetamides as novel non-nucleoside HIV-1 reverse transcriptase inhibitors.

Authors:  Peng Zhan; Xinyong Liu; Zengjun Fang; Zhenyu Li; Christophe Pannecouque; Erik De Clercq
Journal:  Eur J Med Chem       Date:  2009-07-04       Impact factor: 6.514

6.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
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  6 in total

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