1H-imidazole, C16H13Cl3N2OS

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tioconazole. In this structure no classical hydrogen bonds are present but weaker interactions such as C–H×××O (2.821 Ø¥),. C–H×××S (3.644 Ø¥), C–H×××p (3.702 ...
Z. Kristallogr. NCS 230 (2015) 5-6 / DOI 10.1515/ncrs-2014-0210

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© 2015 Walter de Gruyter GmbH, Berlin/Munich/Boston

Crystal structure of 1-[2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole, C16H13Cl3N2OS Pramod B. Pansuriya, Holger B. Friedrich and Glenn E. M. Maguire* School of Chemistry and Physics, University of KwaZulu-Natal, Durban-4000, South Africa Received January 30, 2014, accepted October 07, 2014, available online December 16, 2014, CCDC no. 1267/4200

Experimental details All non-hydrogen atoms were refined anisotropically. All hydrogen atoms were placed in idealised positions and refined in riding models with Uiso assigned the values to be 1.2 or 1.5 times Ueq of the atoms to which they are attached and the constraint distances of C–H ranging from 0.95 Å to 1.00 Å. Discussion Imidazoles are heterocyclic rings that have been used for a wide range of applications such as antifungal-antibiotic drugs, chiral auxiliaries and as ligands for metal complex asymmetric catalysis [2–5]. A number of antifungal drugs' single X-ray diffraction crystal structure have been published [6–9]. The present report includes the novel crystal structure of the antifungal drug tioconazole. In this structure no classical hydrogen bonds are present but weaker interactions such as C–H)))O (2.821 Å), C–H)))S (3.644 Å), C–H)))& (3.702 Å), C–Cl)))& (4.186 Å) create the crystal architecture. &)))& staking generates layering whilst two N)))S (3.042 Å) short contacts between two molecules stabilizes the 22-membered cyclic ring. Table 2. Atomic coordinates and displacement parameters (in Å2).

Abstract C16H13Cl3N2OS, monoclinic, P21/c (no. 14), a = 10.0547(4) Å, b = 9.8289(3) Å, c = 16.6993(7) Å, % = 90.659(2)°, V = 1650.2 Å3, Z = 4, Rgt(F) = 0.0348, wRref(F2) = 0.0891, T = 173 K. Table 1. Data collection and handling. Crystal: Wavelength: $: Diffractometer, scan mode: 2#max: N(hkl)measured, N(hkl)unique: Criterion for Iobs, N(hkl)gt: N(param)refined: Programs:

yellow blocks, size 0.04#0.12#0.13 mm Mo K( radiation (0.71073 Å) 6.86 cm&1 Nonius Kappa CCD, ) and ( 54.94° 7331, 3774 Iobs > 2 "(Iobs), 2835 208 SAINT, SADABS [11], OLEX2 [12], SHELX [13], WinGX [14]

Atom

Site

x

y

H(3) H(4) H(5A) H(5B) H(6) H(8) H(9) H(11) H(13A) H(13B) H(14) H(15) H(16)

4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e

0.6498 0.6063 0.8715 0.8329 0.7801 0.7340 0.8379 0.9547 0.5989 0.5204 0.6706 0.5411 0.3764

0.5966 0.4509 0.5760 0.4434 0.7605 0.5087 0.4964 0.8892 0.8778 0.7359 0.9483 0.9122 0.6853

z 0.3994 0.5118 0.2792 0.2279 0.2383 0.0935 &0.0307 &0.0080 0.1699 0.1654 0.3299 0.4530 0.2859

Uiso 0.037 0.038 0.040 0.040 0.031 0.034 0.036 0.034 0.037 0.037 0.046 0.050 0.042

Source of material The title compound was synthesized using the reported methodology [1]. M.p. = 440–443K. Suitable crystals for X-ray diffraction were obtained by slow evaportion from a dichloromethane/tetrahydrofuran solution at room temperature. _____________

* Correspondence author (e-mail: [email protected])

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C16H13Cl3N2OS

Table 3. Atomic coordinates and displacement parameters (in Å2). Atom

Site

x

y

Cl(1) Cl(2) Cl(3) S(1) O(1) N(1) N(2) C(1) C(2) C(3) C(4) C(5) C(6) C(7) C(8) C(9) C(10) C(11) C(12) C(13) C(14) C(15) C(16)

4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e 4e

0.87282(5) 0.97874(6) 0.86205(6) 0.72304(5) 0.6878(1) 0.5365(2) 0.4219(2) 0.7839(2) 0.7555(2) 0.6799(2) 0.6553(2) 0.7990(2) 0.7184(2) 0.7829(2) 0.7791(2) 0.8402(2) 0.9041(2) 0.9101(2) 0.8498(2) 0.5862(2) 0.5953(2) 0.5234(2) 0.4338(2)

0.19246(5) 0.68441(6) 0.96818(5) 0.26430(5) 0.5819(1) 0.8112(2) 0.7802(2) 0.3106(2) 0.4408(2) 0.5052(2) 0.4234(2) 0.5110(2) 0.7123(2) 0.7049(2) 0.5862(2) 0.5786(2) 0.6916(2) 0.8118(2) 0.8161(2) 0.7891(2) 0.8908(2) 0.8701(2) 0.7473(2)

z 0.30820(3) &0.12387(3) 0.14029(3) 0.45475(3) 0.23241(8) 0.27763(9) 0.3885(1) 0.3626(1) 0.3414(1) 0.4028(1) 0.4663(1) 0.2666(1) 0.2004(1) 0.1184(1) 0.0733(1) &0.0008(1) &0.0304(1) 0.0126(1) 0.0864(1) 0.1969(1) 0.3356(1) 0.4028(1) 0.3129(1)

U11

U22

U33

0.0381(3) 0.0511(3) 0.0522(3) 0.0355(3) 0.0297(7) 0.0266(9) 0.036(1) 0.027(1) 0.027(1) 0.034(1) 0.034(1) 0.031(1) 0.029(1) 0.0223(9) 0.032(1) 0.037(1) 0.030(1) 0.035(1) 0.029(1) 0.031(1) 0.035(1) 0.043(1) 0.030(1)

0.0292(3) 0.0382(3) 0.0243(3) 0.0293(3) 0.0280(7) 0.0341(9) 0.052(1) 0.026(1) 0.025(1) 0.026(1) 0.032(1) 0.034(1) 0.026(1) 0.026(1) 0.025(1) 0.025(1) 0.029(1) 0.022(1) 0.0208(9) 0.037(1) 0.037(1) 0.049(1) 0.040(1)

0.0351(3) 0.0285(3) 0.0374(3) 0.0275(3) 0.0294(7) 0.0269(8) 0.034(1) 0.0245(9) 0.0264(9) 0.033(1) 0.028(1) 0.036(1) 0.0234(9) 0.0250(9) 0.028(1) 0.028(1) 0.0232(9) 0.029(1) 0.028(1) 0.025(1) 0.042(1) 0.034(1) 0.035(1)

Acknowledgments. The authors wish to thank Dr. Hong Su from the Chemistry Department of the University of Cape Town for assistance with the X-ray data collection and refinement and the DST National Research Foundation, Centre of Excellence in Catalysis, c*change, for financial support.

References 1. Burke, B. D.; Chiou, H. M.; Fruchey, O. S.; Nicholas, M. L.: Process to prepare 1-aryl-2-(1-imidazolyl)alkyl ethers and thioethers. WO1997012873 A1 (1997). 2. Schrekker, H. S.; Donato, R. K.; Fuentefri, A. M.; Bergamo, V.; Oliveira, L. F.; Machado, M. M.: Imidazolium salts as antifungal agents: activity against emerging yeast pathogens, without human leukocyte toxicity. MedChemComm 4 (2013) 1457–1460. 3. Mital, A.: Synthetic Nitroimidazoles: Biological Activities and Mutagenicity Relationships. Sci. Pharm. 77 (2009) 497–520. 4. Isobe, T.; Fukuda, K.; Araki, Y.; Ishikawa, T.: Modified guanidines as chiral superbases: the first example of asymmetric silylation of secondary alcohols. Chem. Commun. (2001) 243–244. 5. Ueno, M.; Imaizumi, K.; Sugita, T.; Takata, I.; Takeshita, M.: Effect of a novel anti-rheumatic drug, TA-383, on type II collagen-induced arthritis. Int. J. Immunopharmacol. 17 (1995) 597–603. 6. Carroll, P. J.; Mullen, G. B.; Georgiev, V. St.: Studies on Antifungal Agents. 21. Structure of ($)-cis-3-(4-chlorophenyl)-3-(1H-imidazol-l-ylmethyl)-2-methyl-5-(4-chlorophenoxymethyl)isoxazolidine. Acta Crystallogr. C44 (1988) 1412–1414.

U12 0.0076(2) 0.0016(2) &0.0058(2) 0.0062(2) &0.0017(6) 0.0038(7) 0.0104(9) 0.0018(8) 0.0001(8) 0.0058(8) 0.0074(9) 0.0068(9) &0.0007(8) 0.0016(7) &0.0046(8) &0.0023(8) 0.0018(8) &0.0036(8) &0.0006(8) 0.0046(9) 0.001(1) 0.013(1) 0.0020(9)

U13 0.0058(2) 0.0129(2) 0.0069(2) 0.0042(2) 0.0024(6) 0.0023(7) 0.0069(8) 0.0014(8) &0.0001(8) 0.0007(9) 0.0040(8) 0.0078(9) 0.0014(8) &0.0013(7) &0.0001(8) &0.0026(8) 0.0020(8) 0.0032(8) 0.0006(8) 0.0008(8) &0.001(1) 0.003(1) 0.0024(9)

U23 &0.0040(2) 0.0006(2) &0.0063(2) 0.0063(2) 0.0088(6) 0.0027(7) 0.0049(8) &0.0016(8) 0.0023(8) &0.0003(8) &0.0008(8) 0.0097(9) 0.0054(8) 0.0020(7) 0.0031(8) &0.0017(8) 0.0001(8) 0.0034(8) &0.0015(8) 0.0037(8) &0.008(1) &0.008(1) 0.0039(9)

7. Shin, H. S.; Song, H.; Cho, S. I.; Park, K. I.: The structure of 1-[2-[[(4chlorophenyl)-methyl]thio]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole (Sulconazole) nitrate, C18H16Cl3N3O3S. Bull. Kor. Chem. Soc. 18 (1997) 14–18. 8. Song, H.; Shin, H. S.: The Antifungal Drug Clotrimazole. Acta Crystallogr. C54 (1998) 1675–1677. 9. Ravikumar, K.; Sridhar, B.; Prasad Durga, K.; Bhujanga Rao, A. K. S.: Voriconazole, an antifungal drug. Acta Crystallogr. E63 (2007) o565–o567. 10. Otwinowski, Z.; Minor, W.: Methods in Enzymology, Macromolecular Crystallography, ed. Carter Jr, C. W. & Sweet, R. M., part A, vol. 276, (1997) 307–326, Academic Press. 11. APEX2 and SAINT and SADABS, Bruker AXS Inc., (2006). Madison, Wisconsin, USA. 12. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H.: OLEX2: A complete structure solution, refinement and analysis program. J. Appl. Cryst. 42 (2009) 339–341. 13. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122. 14. Farrugia, L. J.: WinGX and ORTEP for Windows: an update. J. Appl. Crystallogr. 45 (2012) 849–854.

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