Home Physical Sciences The crystal structure of 2-((3-methylthiophen-2-yl)methylene)malononitrile, C9H6N2S
Article Open Access

The crystal structure of 2-((3-methylthiophen-2-yl)methylene)malononitrile, C9H6N2S

  • Abdullah G. Al-Sehemi , Mehboobali Pannipara , Abdullah M. Asiri , Muhammad Nadeem Arshad EMAIL logo and Abul Kalam
Published/Copyright: December 15, 2018

Abstract

C9H6N2S, triclinic, P1̄ (no. 2), a = 3.9497(4) Å, b = 9.0268(13) Å, c = 12.2935(16) Å, V = 431.37(10) Å3, Z = 2, Rgt(F) = 0.0496, wRref(F2) = 0.0747, T = 296(2) K.

CCDC no.: 1519819

The crystal structure is shown in the figure (upper part: ORTEP labelled diagram where thermal ellipsoids were drawn at 50% probability level; middle part: non classical hydrogen bonds). 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 plate
Size:0.40 × 0.18 × 0.03 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.32 mm−1
Diffractometer, scan mode:SuperNova, ω
θmax, completeness:29.1°, >99%
N(hkl)measured, N(hkl)unique, Rint:3141, 2002, 0.018
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1432
N(param)refined:110
Programs:CrysAlisPRO [1], SHELX [2], [3] , WinGX [4]
Table 2:

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

AtomxyzUiso*/Ueq
C10.8402(5)0.1934(3)0.76250(17)0.0406(5)
C20.7663(6)0.3487(3)0.74636(18)0.0457(6)
C30.5738(6)0.4145(3)0.8356(2)0.0573(7)
H30.4999890.5174160.8386910.069*
C40.5069(7)0.3136(3)0.9160(2)0.0599(7)
H40.3828930.3398220.9801380.072*
C51.0300(5)0.0960(3)0.68699(17)0.0417(5)
H51.1151410.1442260.6250610.050*
C61.1072(5)−0.0561(3)0.69057(17)0.0418(5)
C71.3052(6)−0.1318(3)0.60350(19)0.0478(6)
C80.9981(6)−0.1540(3)0.7767(2)0.0517(6)
C90.8726(7)0.4370(3)0.6469(2)0.0596(7)
H9A1.0880370.3873090.6174440.089*
H9B0.8967780.5360810.6661670.089*
H9C0.7011710.4440030.5932360.089*
N11.4635(6)−0.1930(3)0.53487(19)0.0657(6)
N20.9128(7)−0.2348(3)0.8435(2)0.0810(8)
S10.67250(16)0.13381(8)0.88799(5)0.0529(2)

Source of material

The title compound was synthesized by Knoevenagel reaction. To a mixture of 3-methylthiophene-2-carbaldehyde (10 mmol) and malononitrile (10 mmol) in ethanol (100 mL) was added 2 drops of piperidine, stirred for 1−2 h and then cooled to room temperature. The obtained precipitate was filtered off, washed with ethanol and then dried.

Experimental details

The data collection was accomplished using the CrysAlisPro software [1]. The figures were generated through ORTEP and PLATON [4], [5] . All the aromatic C—H hydrogen atoms were positioned geometrically with C—H = 0.93 Å and treated as riding atoms with Uiso(H) was set to 1.2 Ueq(C). Similarly, methyl hydrogen atoms were also positioned geometrically with C—H = 0.96 Å and treated as riding atoms with Uiso(H) was set to 1.5 Ueq(C) for methyl carbon atoms.

Comment

Owing to its multiple biological and electronic properties, thiophene and its derivatives have attracted widespread attention and are treated as important classes of heterocycles due to their existence in a broad spectrum of natural and synthetic organic compounds [6], [7], [8]. Apart from biological activity, due to their structural and electronic properties, compounds having a thiophene core are promising candidates for materials-related applications such as functional materials biosensors, organic field effect transistors (OFETs), organic light-emitting diodes (OLEDs).

In the crystal structure of the title compound (cf. the upper part of the figure), the cyano group is connected to the 3-methyl thiophene moiety through double bond. The molecule is planar as the root mean square (r.m.s.) deviation value of the plane produced from the fitted non-hydrogen atoms of molecules is 0.0408 Å. The largest deviations were observed from the S = 0.0885(1) Å and N = −0.0608(2) Å atoms. The dihedral angle between the thiophene and malononitrile moieties is 4.65(4)°. The crystal structure of the compound is further stabilized by the intermolecular hydrogen bonding interactions (middle and lower part of the figure). These two C—H⋯N type weak interactions connect the molecules along the diagonal of ac-plane. The carbon atom C5 at (x, y, z) position contributes via its hydrogen atom to N1 atom at (−x + 3, − y, − z + 1) and generates a 10 membered ring motif R22(10). Similarly, carbon atom C4 at (x, y, z) position contributes as donor atom via its hydrogen atom to N2 atom at (−x + 1, − y, − z + 2) and generates a 16 membered ring motif R22(16) (middle and lower part of the figure).

Acknowledgements

The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University for funding this work through Research Group Project under grant number R. G. P.1/15/38.

References

1. Agilent Technologies: CrysAlisPRO Software System. Agilent Technologies, Yarnton, England (2012).Search in Google Scholar

2. Sheldrick, G. M.: SHELXT – integrated space-group and crystal-structure determination. Acta Crystallogr. A71 (2015) 3–8.10.1107/S2053273314026370Search in Google Scholar PubMed PubMed Central

3. Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Search in Google Scholar PubMed PubMed Central

4. Farrugia, L. J.: WinGX and ORTEP for Windows: an update. J. Appl. Crystallogr. 45 (2012) 849.10.1107/S0021889812029111Search in Google Scholar

5. Spek, A. L.: Structure validation in chemical crystallography. Acta Crystallogr. D65 (2009) 148–155.10.1107/S090744490804362XSearch in Google Scholar PubMed PubMed Central

6. Norsten, T. B.; Kantchev, E. A. B.; Sullivan, M. B.: Thiophene-containing Pechmann dye derivatives. Org. Lett. 12 (2010) 4816–4819.10.1021/ol1019772Search in Google Scholar PubMed

7. Rouhi, M.; Lakouraj, M. M.; Baghayeri, M.; Hasantabar, V.: Low band gap conductive copolymer of thiophene with p-phenylenediamine and its magnetic nanocomposite: synthesis, characterization and biosensing activity. Int. J. Polymer. Mater. 66 (2017) 12–19.10.1002/pc.24790Search in Google Scholar

8. Ortiz, R. P.; Herrera, H.; Blanco, R.; Huang, H.; Facchetti, A.; Marks, T. J.; Zheng, Y.; Segura, J. L.: Organic n-channel field-effect transistors based on arylenediimide-thiophene derivatives. J. Am. Chem. Soc. 132 (2010) 8440–8452.10.1021/ja1018783Search in Google Scholar PubMed

Received: 2018-09-18
Accepted: 2018-11-21
Published Online: 2018-12-15
Published in Print: 2019-03-26

©2019 Abdullah G. Al-Sehemi et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 Public License.

Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of 1H-indole-5-carboxylic acid – 4,4′-bipyridine (2/1), C14H11N2O2
  3. Crystal structure of ethyl 2-amino-4-(4-ethoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C23H21NO6
  4. Crystal structure of ethyl 2-amino-4-(4-bromothiophen-2-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C16H16BrNO4S
  5. The crystal structure of 6-amino-2-methyl-8-(4-(methylthio)phenyl)-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile – ethanol (1/1), C20H19N5S
  6. Crystal structure of 6-amino-8-(4-isopropylphenyl)-2-methyl-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile-ethanol (1/1), C24H29N5O
  7. Crystal structure of 1,1′-(ethane-1,2-diyl)bis(3-ethyl-1H-imidazol-3-ium)bis(hexafluorido phosphate), C12H20F12N4P2
  8. Crystal structure of dimethyl (3aS,6R,6aS,7S)-2-pivaloyl-2,3-dihydro-1H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isoquinoline-3a1,6a-dicarboxylate, C21H25NO8
  9. Crystal structure of methyl 4-(4-bromothiophen-2-yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H20BrNO3S
  10. Hydrothermal synthesis and crystal structure of catena-poly[bis(4-((pyridin-4-ylmethyl)amino)benzoato-κ3N:O,O′)zinc(II) – 1,2-di(pyridin-4-yl)ethene – water (1/1/1), C38H34N6O5Zn
  11. The crystal structure of 1,2-dimethyl-3,4-dinitrobenzene, C8H8N2O4
  12. Synthesis and crystal structure of trans-tetraaqua-bis(3-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)propanoato-κO)zinc(II) tetrahydrate, C38H48N2O26S2Zn
  13. Crystal structure of diaqua-bis(μ2-6-chloropyridin-2-olato-κ3N,O:O)-tetrakis(chloropyridin-2-olato-κ1O)-bis(penanthroline-κ2N,N′)diterbium(III), C54H38Cl6Tb2N10O8
  14. Crystal structure of oxidobis(piperidine-1-carbodithioato-κ2S,S′)vanadium(IV), C12H20N2OS4V
  15. Crystal structure of 2-((tert-butyldimethylsilyl)oxy)-5-methylisophthalaldehyde, C15H22O3Si
  16. Crystal structure of catena-poly[tetraiodido-(μ2-1,4-bis(2-methyl-1H-imidazol-1-yl)benzene-κ2N:N′)dimercury(II)], C14H14Hg2I4N4
  17. Crystal structure of tetrakis(n-butyl)-(μ2-1,2-bis(2-oxidobenzoyl)hydrazine-1,2-diido-κ6N,O,O′:N′,O′′,O′′′)ditin(IV), C30H44N2O4Sn2
  18. Crystal structure of ethyl 2-amino-4-(4-hydroxy-3-methoxyphenyl)-7-methyl-5-oxo-4H,5H-pyrano-[4,3-b]pyran-3-carboxylate, C19H19NO7
  19. Crystal structure of 3-aminopyrazine-2-carbohydrazide, C5H7N5O
  20. Crystal structure of ethanol-bis(N-((5-(ethoxycarbonyl)-3,4-dimethyl-1H-pyrrol-2-yl)methylene)benzohydrazonato-κ2N,O)copper(II), C36H42N6O7Cu
  21. Crystal structure of 3-methyl-2-oxo-2H-chromen-7-yl propionate, C13H12O4
  22. Crystal structure of 2-(dimethylamino)ethyl 4-aminobenzoate, C11H16N2O2
  23. Crystal structure of 3-(benzo[d]thiazol-2-ylamino)isobenzofuran-1(3H)-one, C15H10N2O2S
  24. Crystal structure of 3-((1H-benzo[d]imidazol-2-yl)amino)-2-(1H-benzo[d]imidazol-2-yl)isoindolin-1-one, C22H16N6O
  25. Crystal structure of (2,2′-bipyridine-κ2N,N′)bis(4-(dimethylamino)phenyldiphenylphosphane-κP)copper(I) tetrafluoroborate, C50H48BCuF4N4P2
  26. Crystal structure of citric acid–acetonitrile (1/1), C8H11NO7
  27. Crystal structure of diethyl 2-(4-methoxyphenyl)-1-phenyl-1,2-dihydropyridine-3,5-dicarboxylate, C24H25NO5
  28. The crystal structure of poly[triaqua-bis(μ3-2,5-dihydroxyterephthalato-κ4O,O′:O′′:O′′′)-(μ4-oxalato-κ4O,O′:O′′,O′′′)cerium(III)], C9H10CeO11
  29. Crystal structure of 1-(5-(anthracen-9-yl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one, C26H22N2O2
  30. Synthesis and crystal structure of 5-(8-(((2-carboxyethyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate trihydrate, C19H23NO12S
  31. Crystal structure of rac-trans-6,6′-((cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-bromophenolato-κ4N,N′,O,O′)-bis(methanol)cobalt(III) chloride, C22H25Br2Co8N2O4Cl
  32. Crystal structure of 1-((R)-(2′-(dimethylamino)-[1,1′-binaphthalen]-2-yl))-3-((S)-2-hydroxy-1-phenylethyl)thiourea, C31H29N3OS
  33. Crystal structure and photochemical property of 1,8-bis(p-tolylthio)pyrene, C30H22S2
  34. Crystal structure of 2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate, C14H18ClN5O4
  35. Crystal structure of ethyl 5-amino-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate, C11H12N4O2
  36. Crystal structure of trichloro-(4-chloro-2,6-bis(diphenylmethyl)-N-((pyridin-2-yl)methylene)aniline)-aluminum dichloromethane solvate, C39H31AlCl6N2
  37. Bis(ethanol-κO)-bis(6-aminopicolinato-κ2N,O)magnesium(II), C16H22O6N4Mg
  38. Crystal structure of catena-poly[aqua-(μ2-1,7-dicarba-closo-dodecaborane-1,7-dicarboxylato-κ2O:O′)-(1,10-phenanthrolin-κ2N,N′)copper(II)], C16H20B10CuN2O5
  39. Crystal structure of (1,2-dicarba-closo-dodecaborane-1,2-dithiolato κ2S,S′)-bis(1,10-phenanthroline κ2N,N′)zinc(II), C26H26B10Zn4S2
  40. Crystal structure of diaqua-bis(1,10-phenanthroline-κ2N,N′)-bis(1,7-dicarba-closo-dodecaborane-1,7-dicarboxylato-κ3O,O′:O′′) dicobalt(II) — ethanol (1/1), C34H46B20Co2N4O11
  41. Crystal structure of ((5,5′-dimethoxy-2,2′-(1,2-phenylenebis(nitrilomethylidyne)))diphenolato-κ4O,N,O′,N′)copper(II), C22H18N2CuO4
  42. Crystal structure of 1-(5-bromo-2-(4-methoxyphenyl)-1H-indol-7-yl)ethan-1-ol, C17H14BrNO2
  43. Crystal structure of (E)-2-(((6-bromopyridin-2-yl)methylene)amino)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one, C34H34N5O2Br
  44. Crystal structure of (Z)-2-((adamantan-1-ylimino)methyl)-5-methoxyphenol, C18H23NO2
  45. Crystal structure of bis((E)-2-ethoxy-6-(((2-hydroxyethyl)imino)methyl)phenolato-κ2N,O)copper(II), C22H28N2CuO6
  46. Crystal structure of 2,3-diphenyl-5,6-bis(4-methoxyphenyl)pyrazine, C30H24N2O2
  47. Crystal structure of dichlorido bis[1-((2,4-dimethyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κN]cadmium(II), Cd(C12H13N5)2Cl2
  48. The crystal structure of 1,5-di(naphthalen-2-yl)-3-(pyridin-2-yl)pentane-1,5-dione, C30H23NO2
  49. The crystal structure of 2-((3-methylthiophen-2-yl)methylene)malononitrile, C9H6N2S
  50. The crystal structure of 1,4-dinitroso-2,3,5,6-tetraacetoxy-piperazine, C12H16N4O10
  51. Crystal structure of bis(2,4,6-trichlorophenyl) malonate, C15H6Cl6O4
  52. The crystal structure of trans-dichlorido-bis(pyridine-2-carboxylato-κ2N,O)platinum(IV), C12H8Cl2N2O4Pt
  53. Crystal structure of 3-nitroquinoline 1-oxide, C9H6N2O3
  54. Crystal structure of 2-(piperidin-1-ium-4-yl)-1H-benzo[d]imidazol-3-ium dichloride dihydrate, C12H21Cl2N3O2
  55. Crystal structure of (4S,4aS,6aR,6bR,12aS,12bR,14aS,14bR)-3,3,6a,6b,9,9,12a-heptamethyloctadecahydro-1H,3H-4,14b-ethanophenanthro[1,2-h]isochromene, C30H50O
  56. Crystal structure of (E)-4-((2-fluoro-3-(trifluoromethyl)benzylidene)amino)-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C11H8F4N4S
  57. Crystal structure of 5-(4-fluorophenyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C9H8FN3S
  58. Crystal structure of catena-poly[(1-(4-fluorophenyl)-N–(5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)methanimine], (C12H14FN3S2Sn)n
  59. The crystal structure of 4-(methoxycarbonyl)benzoic acid, C9H8O4
  60. The crystal structure of N,N′-(6-(thiophen-2-yl)-1,3,5-triazine-2,4-diyl)bis(2-methylpropane-2-sulfonamide) – ethyl acetate(2/1), C34H54N10O6S6
  61. Crystal structure of N′-(1-(2-hydroxyphenyl)ethylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide, C18H17N5O2
  62. Crystal structure of 3-(4-methoxyphenyl)-1-phenylprop-2-yn-1-one, C16H12O2
  63. Crystal structure of N′-(1-(benzofuran-2-yl)ethylidene)-2-cyanoacetohydrazide, C13H11N3O2
  64. Crystal structure of hexa-μ2-chlorido-μ4-oxido-tetrakis(1-vinyl-1H-imidazole-κN)tetracopper(II), C20H24Cu4Cl6N8O
  65. Crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-4-methylbenzenesulfonohydrazide, C22H22O5N2S
  66. Crystal structure of 2-acetyl pyrene, C18H12O
Downloaded on 8.12.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2018-0379/html?srsltid=AfmBOopa-vahpt5NH8uuVI203lNvA59R6AcfbybFX3ZwqmBLQUkhrp5O
Scroll to top button