Startseite Crystal structure of (E)-5-((4-chlorophenyl)diazenyl)-2-(5-(4-fluorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazole, C23H17ClFN5S2
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Crystal structure of (E)-5-((4-chlorophenyl)diazenyl)-2-(5-(4-fluorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazole, C23H17ClFN5S2

  • Gamal A. El-Hiti EMAIL logo , Bakr F. Abdel-Wahab , Mohammed Baashen , Amany S. Hegazy und Benson M. Kariuki
Veröffentlicht/Copyright: 10. Dezember 2016

Abstract

C23H17ClFN5S2, monoclinic, P21/c (no. 14), a = 20.9691(12) Å, b = 11.5316(6) Å, c = 9.2546(4) Å, β = 95.484(4)°, V = 2227.6(2) Å3, Z = 4, Rgt(F) = 0.0468, wRref(F2) = 0.1126, T = 296 K.

CCDC no.:: 1517483

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:Orange needle
Size:0.31 × 0.22 × 0.09 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:3.9 cm−1
Diffractometer, scan mode:SuperNova, ω-scans
2θmax, completeness:59.6°, >83% (>99% for 2θmax = 50°)
N(hkl)measured, N(hkl)unique, Rint:11261, 5322, 0.022
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3684
N(param)refined:327
Programs:CrysAlisPRO [8], SHELX [9], Platon [10]
Table 2

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

AtomxyzUiso*/Ueq
C10.56009(11)0.2098(2)−0.0311(2)0.0600(6)
C20.53105(12)0.1177(2)−0.1040(3)0.0651(7)
H20.54600.0428−0.08500.078*
C30.47962(11)0.1365(2)−0.2056(2)0.0590(6)
H30.45920.0740−0.25400.071*
C40.45845(10)0.24837(19)−0.2355(2)0.0465(5)
C50.48719(11)0.3395(2)−0.1591(2)0.0579(6)
H50.47210.4145−0.17680.070*
C60.53831(11)0.3206(2)−0.0558(3)0.0663(7)
H60.55760.3824−0.00390.080*
C70.33549(9)0.21842(18)−0.5178(2)0.0430(5)
C80.30299(9)0.13926(18)−0.6074(2)0.0431(4)
C90.31527(11)0.01195(19)−0.6067(3)0.0584(6)
H9A0.2752−0.0288−0.62110.088*
H9B0.3373−0.0101−0.51510.088*
H9C0.3412−0.0072−0.68340.088*
C100.25614(9)0.29811(17)−0.6930(2)0.0403(4)
C110.17002(9)0.31616(17)−0.8977(2)0.0427(4)
H110.19510.2697−0.96050.051*
C120.14817(10)0.42874(18)−0.9765(2)0.0472(5)
H12A0.15920.4285−1.07600.057*
H12B0.10230.4397−0.97650.057*
C130.18456(10)0.52095(17)−0.8887(2)0.0442(5)
C140.11712(9)0.24294(16)−0.84667(19)0.0400(4)
C150.10958(11)0.12884(18)−0.8897(2)0.0536(5)
H150.13830.0959−0.94830.064*
C160.05969(13)0.0630(2)−0.8464(3)0.0686(7)
H160.0542−0.0138−0.87560.082*
C170.01877(12)0.1139(2)−0.7598(3)0.0680(7)
C180.02503(12)0.2242(2)−0.7120(3)0.0653(6)
H18−0.00330.2556−0.65120.078*
C190.07501(10)0.28905(19)−0.7565(2)0.0516(5)
H190.08040.3653−0.72490.062*
S10.31014(2)0.36029(4)−0.56204(5)0.04500(14)
S2a0.23680(8)0.74034(13)−0.84240(19)0.0727(5)
C20a0.18176(10)0.64294(18)−0.9238(2)0.0504(5)
C21a0.1410(4)0.6970(7)−1.0207(9)0.0762(18)
H21a0.10960.6578−1.07940.091*
C22a0.1492(4)0.8222(5)−1.0277(11)0.0721(18)
H22a0.12390.8734−1.08570.087*
C23a0.1998(4)0.8499(5)−0.9357(12)0.0766(18)
H23a0.21380.9261−0.92380.092*
S2Ab0.1231(2)0.6918(4)−1.0543(5)0.0716(9)
C20Ab0.18176(10)0.64294(18)−0.9238(2)0.0504(5)
C21Ab0.2191(5)0.7290(8)−0.8785(13)0.072(2)
H21Ab0.25160.7186−0.80390.086*
C22Ab0.2082(9)0.8435(8)−0.949(2)0.075(2)
H22Ab0.23110.9119−0.93090.090*
C23Ab0.1577(9)0.8248(9)−1.045(2)0.074(3)
H23Ab0.14160.8840−1.10600.089*
N10.40778(8)0.27833(16)−0.34273(17)0.0477(4)
N20.38302(8)0.19125(15)−0.41187(17)0.0461(4)
N30.25676(8)0.18466(14)−0.70601(17)0.0418(4)
N40.21285(8)0.36295(14)−0.77539(17)0.0443(4)
N50.22023(8)0.48225(14)−0.77839(18)0.0460(4)
F1−0.03037(9)0.04929(17)−0.7155(2)0.1153(7)
Cl10.62511(3)0.18532(9)0.09640(8)0.0954(3)

aOccupancy: 0.659(3); bOccupancy: 0.341(3).

Source of material

The title compound was synthesized by the reaction of 5-(4-fluorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide and 1-chloro-1-((4-chlorophenyl)diazenyl)propan-2-one in ethanol containing two drops of triethylamine under reflux for 1.5 h. The solid obtained was filtered, dried and recrystallized from dimethylformamide to give orange crystals of the title compound (Mp 212–213 °C) [1].

Experimental details

The thiophenyl moiety is disordered and was refined with a ratio of 34.1(3)/65.9(3) with restrained geometry. All H atoms were placed in calculated positions and refined using a riding model. For the methyl groups, C—H bonds were fixed at 0.96 Å and Uiso set to 1.5Ueq(C) with free rotation around the C—C bond (HFIX 137 in SHELX [9]). For the rest of the hydrogens, Uiso was set to 1.2Ueq(C) with a distance of 0.93 Å for aromatic C—H. For CH and CH2 groups, the C—H distances were set to 0.98 and 0.97 Å respectively.

Discussion

Compounds bearing thiazole and pyrazole nuclei are found to have various antimicrobial activities such as antibacterial, antifungal and antitumor [1], [2], [3], [4], [5], [6], [7].

The asymmetric unit (cf. the figure) of the crystal structure consists of a molecule of C23H17ClFN5S2 with a disordered thiophenyl fragment. Apart from the fluorobenzene group, the rest of the molecule is essentially planar; the angles between the planes of neighbouring rings are 13° or less. The plane of the fluorobenzene is perpendicular (90.71(5)°) to the plane of the pyrazolinyl group. In the crystal, the molecules stack along [001] with interplanar distances of about 3.5 Å between glide-plane related molecules.

Acknowledgements

The authors extend their appreciation to the College of Applied Medical Sciences Research Centre and the Deanship of Scientific Research at King Saud University for funding and to Cardiff University for continued support.

References

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Received: 2016-7-5
Accepted: 2016-11-16
Published Online: 2016-12-10
Published in Print: 2017-1-1

©2016 Gamal A. El-Hiti et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Editorial
  3. Twenty years of crystal structure publication and the road ahead
  4. Crystal Structures
  5. Crystal structure of poly-[triaqua-(μ4-5′-carboxy-[1,1′-biphenyl]-2,3,3′-tricarboxylate-κ6O1,O2:O3,O4:O5:O6)praseodymium(III), C16H13O11Pr
  6. Crystal structure of (R)-1-(2,3-dihydro-1H-pyrrolizin-5-yl)-2,3-dihydroxypropan-1-one, C10H13NO3
  7. Crystal structure of (E)-4-nitro-2-((2-phenoxyphenylimino)methyl)phenol, C19H14N2O4
  8. Crystal structure of 3,3′-di(furan-2-yl)-5,5′-bi-1,2,4-triazine
  9. Crystal structure of 11-(p-coumaroyloxy)-tremetone, C22H20O5
  10. The crystal structure of 1,3-bis(2,6-diiso-propylphenyl)imidazol-2-ylidene)-dibromido-(1-methyl-1H-imidazole-κ1N)palladium(II) – ethyl acetate – water (1/1/1), C31H42Br2N4Pd
  11. Crystal structure of 2-((3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)-1H-indene-1,3(2H)-dione, C28H19N5O2
  12. Crystal structure of 2-(5-(4-fluorophenyl)-3-p-tolyl-4,5-dihydro-1H-pyrazol-1-yl)-4-(5-methyl-1-p-tolyl-1H-1,2,3-triazol-4-yl)thiazole, C29H25FN6S
  13. Crystal structure of poly-[aqua-(μ7-benzene-1,3,5-tricarboxylato)-(μ3-1,2,4-triazol-1-ido)dicobalt(II)], C11H7Co2N3O7
  14. Crystal constructure of 16(S)-methyl-6α-carboxy-1, 15-dioxo-6, 7-seco-ent-kaur-2-en-7, 20-olide, C20H24O6
  15. Crystal structure of 1-(benzo[d]thiazol-2-yl)-3-phenylthiourea, C14H11N3S2
  16. Crystal structure of 3-(2-bromophenyl)-1,1-dimethylthiourea, C9H11BrN2S
  17. Crystal structure of 1-(adamantan-1-yl)-3-(3-chlorophenyl)thiourea, C17H21ClN2S
  18. Crystal structure of 3-(adamantan-1-yl)-1-(4-bromophenyl)urea, C17H21BrN2O
  19. Crystal structure of (Z)-Ethyl 2-cyano-2-(3-phenylthiazolidin-2-ylidene) acetate, C14H14N2O2S
  20. Crystal structure of methyl 2b-ethyl-1a,2a,2b,2b1,3,5,10,11-octahydro-1H-oxireno[2′,3′:6,7]indolizino[8,1-cd]carbazole-4-carboxylate, C21H24N2O3
  21. Crystal structure of 2-amino-5-oxo-4-(3,4,5-trimethoxy-phenyl)-4,5,6,7-tetrahydro-cyclopenta[b]pyran-3-carbonitrile, C18H18N2O5
  22. Crystal structure of 1,2,3-trimethyl-2,3-dihydro-1H-perimidine, C14H16N2
  23. Crystal structure of bis(2,6-dihydroxymethyl)pyridine-κ3N,O,O′)-bis(μ2-6-chloropyridin-2-olato-κ3N,O:O)-bis(6-chloropyridin-2-olato-κO)-bis(nitrato-κ2O,O′)digadolinium(III), C34H30Cl4Gd2N8O14
  24. Crystal structure of 8-isopropyl-8-aza-bicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate, C19H27NO3
  25. Crystal structure of 1-methyl-3-[((naphthalen-2-ylsulfonyl)oxy)imino]indolin-2-one, C19H14N2O4S
  26. Crystal structure (7,8-bis(diisopropylphosphino)-7,8-dicarba-nido-undecaborane-κ2P,P′)-(benzoato-κ2O,O′)nickel(II), C21H42B9NiO2P2
  27. Crystal structure of methyl-2-methyl-4-(2-oxo-2-phenylethyl)-5-phenyl-1H-pyrrole-3-carboxylate, C21H19NO3
  28. Crystal structure of 2-[(2-oxo-thiazolidine-3-carbonyl)sulfamoyl]-methy-benzoic acid methyl ester, C13H14N2O6S2
  29. Crystal structure of N′-(2-phenylacetyl)thiophene-2-carbohydrazide monohydrate, C13H14N2O3S
  30. Crystal structure of 1,1′-(hexane-1,6-diyl)bis(3-methyl-1H-imidazol-3-ium) bis(hexafluoro phosphate), C14H24F12N4P2
  31. Crystal structure of di-μ-chlorido-bis[1,2-bis(dicyclohexylphosphino)-1,2-dicarba-closo-dodecaborane-κ2P,P′]zinc(II), C52H108B20Cl2P4Zn2
  32. Crystal structure of dibromido-bis[μ-1-[(2-methyl-1H-benzoimidazol-1-yl)methyl]-1H-benzotriazole-κN]mercury(II), C30H26Br2HgN10
  33. Crystal structure of bis(μ-nitrato-κ2O:O)-bis[1,2-bis(diphenylphosphino)-1,2-dicarba-closo-dodecaborane-κ2P,P′]disilver(I) dicloromethane monosolvate, C54H64B20Cl4O6P4Ag2
  34. Crystal structure of dinuclear dichloridobis(dimethylformamide-kO)bis[μ2-3-(2-oxyphenyl)-5-(pyrazin-2-yl)-1,2,4-triazol-1ido-κ4-O,N:N′,N′′(2)]diiron(III) dimethylformamide (1/1), C36H42Cl2Fe2N14O6
  35. Crystal structure of diaqua-dinitrato-κO-bis(4-(1H-pyrazol-3-yl)pyridine-κN)manganese(II), C16H18MnN8O8
  36. Crystal structure of (Z)-6-methoxy-2-(2,2,2-trifluoro-1-hydroxyethylidene)-2,3-dihydro-1H-inden-1-one, C12H6F6O3
  37. Crystal Structure of 4-(2-chloroacetamido)pyridinium chloride monohydrate, C7H10Cl2N2O2
  38. Crystal structure of 2-amino-4-(4-chloro-phenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H13ClN2O2
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  41. Crystal structure of 3-(2-(4-chlorophenyl)-3-hydroxy-3,3-diphenylpropyl)-1,1-dimethylurea, C24H25ClN2O2
  42. Crystal structure of 3-(4-chlorophenyl)-1,1-dimethylthiourea, C9H11ClN2S
  43. Crystal structure of 2-amino-4-(4-bromo-phenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile, C16H11BrN2O3
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  48. The crystal structure of 1-(4-bromophenyl)-2-(4-(4-fluorophenyl)piperazin-1-yl)ethanol, C18H20BrFN2O1
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  51. Crystal structure of 2-[3,5-bis(trifluoromethyl)benzylsulfanyl]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C15H7BrF6N2OS2
  52. Crystal structure of (E)-3-((naphthalen-1-ylimino)methyl)-4-nitrophenol, C17H12N2O3
  53. Crystal structure of 2-dichloromethyl-2-p-nitrophenyl-1,3-dioxolane, C10H9Cl2NO4
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  55. Crystal structure of 2-(4-oxo-2-thioxothiazolidin-3-yl)acetic acid monohydrate, C5H7NO4S2
  56. Crystal structure of a P4-bridged (η5-pentamethyl-cyclopentadienyl)(η5-adamantylcyclopentadienyl) titanium(III)complex, C50H66P4Ti2
  57. Crystal structure of cis-bis(2,2′-bipyrimidine-κ2N,N′)bis(thiocyanato-κN)nickel(II), C18H12N10NiS2
  58. Crystal structure of cis-bis(2,2′-bipyridine-κ2N,N′)dibromidomanganese(II), C20H16Br2MnN4
  59. Crystal structure of cis-bis(2,2′-bipyridine-κ2N,N′)bis(thiocyanato-κN)nickel(II), C22H16N6NiS2
  60. Crystal structure of trans-dibromido(1,4,8,11-tetraazacyclotetradecane)nickel(II), C10H24Br2N4Ni
  61. Crystal structure of cis-tetrabromidobis(pyridine-κN)platinum(IV), C10H10Br4N2Pt
  62. Crystal structure of (E)-5-((4-chlorophenyl)diazenyl)-2-(5-(4-fluorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazole, C23H17ClFN5S2
  63. The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridocobaltate(II) monohydrate, C10H18Cl4CoN2O
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