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BY-NC-ND 4.0 license Open Access Published by De Gruyter (O) June 27, 2018

Crystal structure of 3,6-diphenyl-7H-[1,2,4]-triazolo[3,4-b][1,3,4]thiadiazine, C16H12N4S

  • Qichun Ding EMAIL logo , Shudong Dai and Li-Xue Zhang

Abstract

C16H12N4S, monoclinic, P21/c (no. 14), a = 22.151(4) Å, b = 12.484(2) Å, c = 10.2018(19) Å, β = 101.073(6)°, Z = 8, V = 2768.7(8) Å3, Rgt(F) = 0.0522, wRref(F2) = 0.1428, T = 296(2) K.

CCDC no.: 1848852

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless block
Size:0.26 × 0.24 × 0.21 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.23 mm−1
Diffractometer, scan mode:Bruker APEX-II CCD, φ and ω
θmax, completeness:27.5°, 99%
N(hkl)measured, N(hkl)unique, Rint:17351, 6303, 0.068
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3985
N(param)refined:380
Programs:Bruker [8], Olex2 [9]
Table 2:

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

AtomxyzUiso*/Ueq
S11.01482(3)0.68847(5)0.77855(6)0.04353(18)
S20.48839(3)0.30632(5)0.76545(6)0.0492(2)
N10.95194(8)0.40743(15)0.82570(19)0.0449(5)
N20.99357(8)0.47456(16)0.7820(2)0.0457(5)
N30.93564(7)0.57024(14)0.88822(17)0.0355(4)
N40.90355(8)0.65660(14)0.92540(17)0.0370(4)
N50.55283(9)0.58464(16)0.8805(2)0.0504(5)
N60.51109(9)0.51971(17)0.7965(2)0.0507(5)
N70.56759(7)0.41840(15)0.94700(17)0.0377(4)
N80.59874(8)0.32982(15)1.00728(18)0.0392(4)
C10.84670(11)0.4669(2)1.0500(3)0.0532(6)
H10.86461(11)0.5300(2)1.0874(3)0.0638(8)*
C20.80011(13)0.4193(2)1.1012(3)0.0667(8)
H20.78647(13)0.4506(2)1.1730(3)0.0800(10)*
C30.77386(12)0.3264(2)1.0471(3)0.0681(8)
H30.74245(12)0.2946(2)1.0821(3)0.0818(10)*
C40.79359(12)0.2802(2)0.9418(3)0.0629(8)
H40.77576(12)0.2167(2)0.9054(3)0.0755(9)*
C50.83969(11)0.32705(19)0.8893(3)0.0508(6)
H50.85291(11)0.29561(19)0.8172(3)0.0610(8)*
C60.86659(10)0.42138(18)0.9440(2)0.0394(5)
C70.91681(9)0.46518(17)0.8869(2)0.0366(5)
C80.98255(9)0.57112(18)0.8195(2)0.0373(5)
C90.99639(9)0.76330(18)0.9161(2)0.0382(5)
H9a1.02451(9)0.74270(18)0.9972(2)0.0459(6)*
H9b1.00259(9)0.83891(18)0.9013(2)0.0459(6)*
C100.93178(9)0.74662(17)0.9355(2)0.0360(5)
C110.89831(9)0.83837(17)0.9776(2)0.0354(5)
C120.86073(10)0.82380(19)1.0706(2)0.0438(6)
H120.85573(10)0.75574(19)1.1040(2)0.0526(7)*
C130.83102(11)0.9094(2)1.1131(3)0.0517(6)
H130.80652(11)0.8993(2)1.1766(3)0.0620(8)*
C140.83700(11)1.0098(2)1.0632(3)0.0530(7)
H140.81623(11)1.0674(2)1.0918(3)0.0636(8)*
C150.87351(11)1.0250(2)0.9714(3)0.0562(7)
H150.87750(11)1.0932(2)0.9371(3)0.0675(8)*
C160.90450(11)0.93999(18)0.9291(2)0.0479(6)
H160.92978(11)0.95123(18)0.8674(2)0.0575(7)*
C170.66889(12)0.6492(2)1.0444(3)0.0624(7)
H170.65950(12)0.6814(2)0.9607(3)0.0749(9)*
C180.71533(14)0.6898(3)1.1404(4)0.0843(10)
H180.73757(14)0.7490(3)1.1212(4)0.1012(13)*
C190.72905(13)0.6434(3)1.2642(4)0.0836(11)
H190.76033(13)0.6716(3)1.3290(4)0.1003(13)*
C200.69702(12)0.5563(3)1.2926(3)0.0711(9)
H200.70658(12)0.5249(3)1.3767(3)0.0854(11)*
C210.65051(11)0.5143(2)1.1973(3)0.0539(7)
H210.62870(11)0.4548(2)1.2171(3)0.0647(8)*
C220.63624(10)0.5609(2)1.0721(2)0.0454(6)
C230.58649(10)0.52270(18)0.9682(2)0.0410(5)
C240.52124(10)0.42145(19)0.8371(2)0.0418(5)
C250.56951(9)0.24114(19)0.9902(2)0.0379(5)
C260.50434(9)0.23081(19)0.9186(2)0.0430(6)
H26a0.47731(9)0.25522(19)0.9768(2)0.0516(7)*
H26b0.49537(9)0.15585(19)0.8987(2)0.0516(7)*
C270.60174(9)0.14638(18)1.0556(2)0.0385(5)
C280.64398(11)0.1569(2)1.1740(2)0.0516(6)
H280.65265(11)0.2244(2)1.2116(2)0.0619(8)*
C290.67308(11)0.0685(2)1.2361(3)0.0599(7)
H290.70089(11)0.0764(2)1.3163(3)0.0719(9)*
C300.66173(11)−0.0307(2)1.1817(3)0.0586(7)
H300.68189(11)−0.0901(2)1.2244(3)0.0703(9)*
C310.62046(11)−0.0430(2)1.0636(3)0.0569(7)
H310.61284(11)−0.1106(2)1.0257(3)0.0683(8)*
C320.59043(10)0.0455(2)1.0018(2)0.0480(6)
H320.56210(10)0.0369(2)0.9225(2)0.0576(7)*

Source of material

The title compound was prepared by the reaction of 4-amino-3-phenyl-1H-1,2,4-triazole-5(4H)-thione (2 mmol) and 2-bromo-1-phenylethanone (2 mmol) in ethanol (40 mL). The mixture was refluxed for 2 h and the solid obtained on cooling was filtered, washed with cold water, dried and recrystallized from ethanol. The purified product was dissolved in ethanol and crystals were obtained after 7 days by slow evaporation of the ethanol solution at room temperature.

Experimental details

All H atoms were positioned geometrically and allowed to ride on their parent atoms at distances of Csp2-H = 0.93 Å with Uiso = 1.2 Ueq (parent atom), and Csp3-H = 0.96 or 0.97 Å with Uiso = 1.5 Ueq (parent atom).

Comment

1,2,4-Triazolo[3,4-b][1,3,4]thiadiazine derivatives have attracted considerable attention. Most of them have been shown to possess biological activities [1], [2], [3], [4], [5], [6], [7], such as antitubulin, anticancer, antitubercular, antimicrobial, antimycobacterial, antibacterial.

In the title crystal structure there are two crystallographic independent molecules in the asymmetric unit. All bond lengths and angles are in normal range. The triazole ring and the thiadiazine ring in each independent molecule are almost coplanar, with the dihedral angle of 7.32(13)° and 9.27(12)°, respectively. The dihedral angle between the two triazole rings is 83.36(0.28)° and that between the two thiadiazine rings is 82.94(4)°. Both the S—C and C—N bond lengths are in agreement with the values in related compounds. The short C—N bond lengths of 1.304(3) Å (N1—C7), 1.301(3) Å (N2—C8), 1.304(3) Å (N5—C23) and 1.300(3) Å (N6—C24), respectively, suggest partially localized double bonds. The C—N bond lengths are 1.280(3) Å (N4—C10) and 1.277(3) Å (N8—C25), respectively, which are shorter than the typical C=N bond length (1.34 Å–1.38 Å).

Acknowledgements

We are grateful for financial support from Zhangzhou Science and Technology Program Project of China (No. ZZ2018J39).

References

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Received: 2018-03-16
Accepted: 2018-06-12
Published Online: 2018-06-27
Published in Print: 2018-08-28

©2018 Qichun Ding et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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