Home Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C13H12N2O3
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Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C13H12N2O3

  • Reem I. Al-Wabli , Alwah R. Al-Ghamdi , Hazem A. Ghabbour and Mohamed I. Attia EMAIL logo
Published/Copyright: March 23, 2017
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 232 Issue 3

Abstract

C13H12N2O3, monoclinic, P21/n (no. 14), a = 7.3322(5) Å, b = 8.0341(5) Å, c = 19.4479(14) Å, β = 95.775(2)°, V = 1139.82(13) Å3, Z = 4, Rgt(F) = 0.0533, wRref(F2) = 0.1335, T = 293(2) K.

CCDC no.:: 1513740

The 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:0.53 × 0.30 × 0.24 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.0 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
2θmax, completeness:55°, >99%
N(hkl)measured, N(hkl)unique, Rint:15327, 2619, 0.069
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1782
N(param)refined:163
Programs:Bruker programs [26], SHELX [27, 28]
Table 2

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

AtomxyzUiso*/Ueq
O1−0.32584(19)0.3882(2)0.54491(7)0.0586(4)
O2−0.1784(2)0.18701(19)0.48625(7)0.0599(4)
O30.17088(19)0.70432(18)0.69870(7)0.0553(4)
N10.6623(2)0.55756(18)0.80766(7)0.0375(4)
N20.8445(3)0.4049(3)0.87925(10)0.0646(5)
C1−0.3535(3)0.2516(3)0.49832(11)0.0608(6)
H1A−0.41890.28830.45510.073*
H1B−0.42570.16600.51800.073*
C2−0.0534(3)0.2699(2)0.53079(9)0.0421(5)
C30.1311(3)0.2462(3)0.54163(10)0.0491(5)
H3A0.19000.16540.51770.059*
C40.2275(3)0.3490(2)0.59033(9)0.0418(5)
H4A0.35340.33470.59980.050*
C50.1409(2)0.4718(2)0.62493(8)0.0331(4)
C6−0.0492(2)0.4951(2)0.61174(9)0.0378(4)
H6A−0.10970.57830.63370.045*
C7−0.1411(2)0.3902(2)0.56534(9)0.0395(4)
C80.2424(2)0.5806(2)0.67726(9)0.0347(4)
C90.4340(2)0.5335(2)0.70589(9)0.0387(4)
H9A0.51840.55960.67210.046*
H9B0.43940.41450.71420.046*
C100.4930(3)0.6241(3)0.77239(10)0.0478(5)
H10A0.51020.74100.76240.057*
H10B0.39640.61580.80290.057*
C110.8367(3)0.5899(3)0.79383(11)0.0513(5)
H11A0.87350.66220.76050.062*
C120.9454(3)0.4958(3)0.83824(12)0.0627(6)
H12A1.07270.49350.84040.075*
C130.6752(3)0.4464(3)0.85915(10)0.0497(5)
H13A0.57440.40330.87860.060*

Source of material

A mixture of 1-(2H-1,3-benzodioxol-5-yl)ethanone (3.28 g, 20 mmol), dimethylamine hydrochloride (2.20 g, 27 mmol), paraformaldehyde (0.81 g, 9.0 mmol) in absolute ethanol (15 mL) and a catalytic amount of concentrated hydrochloric acid (0.5 mL) was heated to reflux for two hours. The reaction mixture was cooled and acetone (30 mL) was added. The precipitated Mannich base hydrochloride, namely 1-(2H-1,3-benzodioxol-5-yl)-3-(dimethylamino)propan-1-one hydrochloride was filtered off and dried. The Mannich base hydrochloride (2.58 g, 10 mmol) was dissolved in water (10 mL) and imidazole (1.36 g, 20 mmol) was added. The reaction mixture was heated to reflux for five hours, cooled and the precipitated solid was collected by filtration to give 1.15 g (47%) of the title ketone as a white solid (m.p. 423–425 K). Slow evaporation of an ethanolic solution of the title compound furnished its colourless single crystals.

Experimental details

Carbon-bound hydrogen atoms were placed in calculated positions and were included in the refinement using the riding model approximation, with Uiso(H) set to 1.2Ueq(C).

Discussion

Imidazole derivatives have been first synthesised in the 1840s. Their current importance is testified by their ubiquitousness in the fields of medicinal chemistry, material science and agrochemicals [1]. Imidazole-based compounds exhibit diverse biological activities anticancer [2], [3], [4], [5] antibacterial [6, 7] , antitubercular [8, 9] , antifungal [10, 11] , antiviral [12], [13], [14], anticonvulsant [15], [16], [17] and antiparkinson’s agents [18, 19] . The discovery of the broad spectrum antifungal drug clotrimazole sparked considerable interest in their antifungal properties. Thereafter, research focused on incorporating the imidazole pharmacophore in different chemical structures [20], [21], [22]. In addition, a literature search revealed that a plethora of bioactive molecules incorporate the 1,3-benzodioxole scaffold in their structure [23], [24], [25]. The title ketone is a hybrid structure bearing both the 1,3-benzodioxole and imidazole moieties in its structure and can be used as a precursor to synthesize a number of new bioactive surrogates.

In the crystal structure of the title compound, the asymmetric unit contains one independent molecule. The molecules are packed via several non-classical C—H ⋯O intermolecular hydrogen bonds to give a 3-D network.

Acknowledgement

This research project was supported by a grant from the Research Center of the Female Scientific and Medical Colleges, Deanship of Scientific Research, King Saud University.

References

1 Jin, Z.: Muscarine, imidazole, oxazole, and thiazole alkaloids. Nat. Prod. Rep. 28 (2011) 1143–1191.10.1039/c0np00074dSearch in Google Scholar PubMed

2 Li, Q. Y.; Deng, X. Q.; Zu, Y. G.; Lv, H.; Su, L.; Yao, L.; Zhang, Y.; Li, L.: Cytotoxicity and topo I targeting activity of substituted 10–nitrogenous heterocyclic aromatic group derivatives of SN-38. Eur. J. Med. Chem. 45 (2010) 3200–3206.10.1016/j.ejmech.2010.03.013Search in Google Scholar PubMed

3 Lu, Y.; Li, C. M.; Wang, Z.; Ross, C. R.; Chen, J.; Dalton, J. T.; Li, W.; Miller, D. D.: Discovery of 4-substituted methoxybenzoyl-aryl-thiazole as novel anticancer agents: synthesis, biological evaluation, and structure-activity relationships. J. Med. Chem. 52 (2009) 1701–1711.10.1021/jm801449aSearch in Google Scholar PubMed PubMed Central

4 Biersack, B.; Muthukumar, Y.; Schobert, R.; Sasse, F.: Cytotoxic and antivascular 1-methyl-4-(3-fluoro-4-methoxyphenyl)-5-(halophenyl)-imidazoles. Bioorg. Med. Chem. Lett. 21 (2011) 6270–6273.10.1016/j.bmcl.2011.09.005Search in Google Scholar PubMed

5 Chen, J.; Ahn, S.; Wang, J.; Lu, Y.; Dalton, J. T.; Miller, D. D.; Li, W.: Discovery of novel 2-aryl-4-benzoyl-imidazole (ABI-III) analogues targeting tubulin polymerization as antiproliferative agents. J. Med. Chem. 55 (2012) 7285–7289.10.1021/jm300564bSearch in Google Scholar PubMed PubMed Central

6 Sharma, S.; Gangal, S.; Rauf, A.: Convenient one-pot synthesis of novel 2-substituted benzimidazoles, tetrahydrobenzimidazoles and imidazoles and evaluation of their in vitro antibacterial and antifungal activities. Eur. J. Med. Chem. 44 (2009) 1751–1757.10.1016/j.ejmech.2008.03.026Search in Google Scholar PubMed

7 Aonofriesei, F.; Lupsor, S.: Inhibitory potential of a novel imidazole derivative as evaluated by time-kill and dehydrogenase activity. Curr. Microbiol. 66 (2013) 162–168.10.1007/s00284-012-0252-ySearch in Google Scholar PubMed

8 Stover, C. K.; Warrener, P.; VanDevanter, D. R.; Sherman, D. R.; Arain, T. M.; Langhorne, M. H.; Anderson, S. W.; Towell, J. A.; Yuan, Y.; McMurray, D. N.; Kreiswirth, B. N.: A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis. Nature 405 (2000) 962–966.10.1038/35016103Search in Google Scholar PubMed

9 Lima, C. H. S.; Henriques, M. G. M. O.; Candea, A. L. P.; Lourenco, M. C. S.; Bezerra, F. A. F. M.; Ferreira, M. L.; Kaiser, C. R.; de Souza, M. V. N.: Synthesis and antimycobacterial evaluation of N′-(E)-heteroaromaticpyrazine-2-carbohydrazide derivatives. Med. Chem. 7 (2011) 245–249.10.2174/157340611795564303Search in Google Scholar PubMed

10 Polak, A.: Oxiconazole, a new imidazole derivative. Evaluation of antifungal activity in vitro and in vivo. Arzneimittelforschung 32 (1981) 17–24.Search in Google Scholar

11 Rossello, A.; Bertini, S.; Lapucci, A.; Macchia, M.; Martinelli, A.; Rapposelli, S.; Herreros, E.; Macchia, B.: Synthesis, antifungal activity, and molecular modeling studies of new inverted oxime ethers of oxiconazole. J. Med. Chem. 45 (2002) 4903–4912.10.1021/jm020980tSearch in Google Scholar PubMed

12 Zhan, P.; Liu, X.; Zhu, J.; Fang, Z.; Li, Z.; Pannecouque, C.; De Clercq, E.: Synthesis and biological evaluation of imidazole thioacetanilides as novel non-nucleoside HIV-1 reverse transcriptase inhibitors. Bioorg. Med. Chem. 17 (2009) 5775–5781.10.1016/j.bmc.2009.07.028Search in Google Scholar PubMed

13 Basu, A.; Jasu, K.; Jayaprakash, V.; Mishra, N.; Ojha, P.; Bhattacharya, S.: Development of CoMFA and CoMSIA models of cytotoxicity data of anti-HIV-1-phenylamino-1H-imidazole derivatives. Eur. J. Med. Chem. 44 (2009) 2400–2407.10.1016/j.ejmech.2008.09.043Search in Google Scholar PubMed

14 Jia, W.; Zhao, Y.; Li, R.; Wu, Y.; Li, Z.; Gong, P.: Synthesis and in–vitro anti–hepatitis–B virus activity of 6H–[1]benzothiopyrano [4,3–b]quinolin–10–ols. Arch. Pharm. 342 (2009) 507–512.10.1002/ardp.200900070Search in Google Scholar PubMed

15 Karakurt, A.; Alagöz, M. A.; Sayoğlu, B.; Calış, U.; Dalkara, S.: Synthesis of some novel 1-(2-naphthyl)-2-(imidazol-1-yl)ethanone oxime ester derivatives and evaluation of their anticonvulsant activity. Eur. J. Med. Chem. 57 (2012) 275–282.10.1016/j.ejmech.2012.08.037Search in Google Scholar PubMed

16 Karakurt, A.; Ozalp, M.; Işık, Ş.; Stables, J. P.; Dalkara, S.: Synthesis, anticonvulsant and antimicrobial activities of some new 2-acetylnaphthalene derivatives. Bioorg. Med. Chem. 18 (2010) 2902–2911.10.1016/j.bmc.2010.03.010Search in Google Scholar PubMed

17 Caliş, U.; SeptioğluEbubekir, S.; Aytemir, M. D.: Synthesis and anticonvulsant evaluation of some novel (thio) semicarbazone derivatives of arylalkylimidazole. Arzneimittelforschung 61 (2011) 327–334.10.1055/s-0031-1296206Search in Google Scholar

18 Sugimoto, Y.; Kobayashi, K.; Asai, M.; Ohno, A.; Yamada, K.; Ozaki, S.; Ohta, H.; Okamoto, O.: Synthesis and biological evaluation of imidazole derivatives as novel NOP/ORL1 receptor antagonists: Exploration and optimization of alternative pyrazole structure. Bioorg. Med. Chem. Lett. 19 (2009) 4611–4616.10.1016/j.bmcl.2009.06.095Search in Google Scholar PubMed

19 Asproni, B.; Murineddu, G.; Pau, A.; Pinna, G. A.; Langgård, M.; Christoffersen, C. T.; Nielsen, J.; Kehler, J.: Synthesis and SAR study of new phenylimidazole-pyrazolo [1, 5-c] quinazolines as potent phosphodiesterase 10A inhibitors. Bioorg. Med. Chem. 19 (2011) 642–649.10.1016/j.bmc.2010.10.038Search in Google Scholar PubMed

20 Aboul-Enein, M. N.; El-Azzouny, A. A.; Attia, M. I.; Saleh, O. A.; Kansoh, A. L.: Synthesis and anti–candida potential of certain novel 1–[(3–substituted–3–phenyl) propyl]–1H–imidazoles. Arch. Pharm. 344 (2011) 794–801.10.1002/ardp.201000224Search in Google Scholar PubMed

21 De Vita, D.; Scipione, L.; Tortorella, S.; Mellini, P.; Di Rienzo, B.; Simonetti, G.; D’Auria, F. D.; Panella, S.; Cirilli, R.; Di Santo, R.; Palamara, A. T.: Synthesis and antifungal activity of a new series of 2-(1H-imidazol-1-yl)-1-phenylethanol derivatives. Eur. J. Med. Chem. 49 (2012) 334–342.10.1016/j.ejmech.2012.01.034Search in Google Scholar PubMed

22 El Hage, S.; Lajoie, B.; Feuillolay, C.; Roques, C.; Baziard, G.: Synthesis, antibacterial and antifungal activities of bifonazole derivatives. Arch. Pharm. 344 (2011) 402–410.10.1002/ardp.201000304Search in Google Scholar PubMed

23 Micale, N.; Zappalà, M.; Grasso, S.: Synthesis and cytotoxic activity of 1,3-benzodioxole derivatives. Farmaco 58 (2003) 351–355.10.1002/chin.200336096Search in Google Scholar

24 Leite, A. C. L.; da Silva, K. P.; de Souza, I. A.; de Araújo, J. M.; Brondani, D. J.: Synthesis, antitumour and antimicrobial activities of new peptidyl derivatives containing the 1,3-benzodioxole system. Eur. J. Med. Chem. 39 (2004) 1059–1065.10.1016/j.ejmech.2004.09.007Search in Google Scholar PubMed

25 Aboul-Enein, M. N.; El-Azzouny, A. A.; Attia, M. I.; Maklad, Y. A.; Amin, K. M.; Abdel-Rehim, M.; El-Behairy, M. F.: Design and synthesis of novel stiripentol analogues as potential anticonvulsants. Eur. J. Med. Chem. 47 (2012) 360–369.10.1016/j.ejmech.2011.11.004Search in Google Scholar PubMed

26 Bruker. APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA, (2009).Search in Google Scholar

27 Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed

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

Received: 2016-11-2
Accepted: 2017-3-5
Published Online: 2017-3-23
Published in Print: 2017-5-24

©2017 Reem I. Al-Wabli et al., published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of 2,5-diiodo-4-nitro-1H-imidazole hemihydrate, C6H4I4N6O5
  3. Crystal structure of catena-poly[μ2-2,2′-(1,3-phenylene)diacetato-κ4O,O′:O′′,O′′′)-(μ2-1,6-bis(2-methyl-1H-benzo[d]imidazol-1-yl)hexane-κ2N:N′)cadmium(II)], C32H34CdN4O4
  4. Crystal structure of poly[aqua-(2,2′-bipyridine-κN,N′)-(μ4-5,5′-(hexane-1,6-diyl)-bis(oxy)diisophthalato κ8O1,O2:O3,O4:O5,O6:O7,O8)manganese(II)], C21H21MnN2O7
  5. Crystal structure of poly-[(μ2-((1,3-bis(benzimidazol-1-yl)propane-κ2N:N′)(μ2-4-tert-butyl-phthalato-κ2O:O′)cobalt(II)] monohydrate, C29H30CoN4O5
  6. Crystal structure of 2-amino-4-(3,4,5-trimethoxy-phenyl)-5-(oxo-5,6,7,8-tetrahydro-4H-chromene)-3-carbonitrile – ethanol (1/1), C21H26N2O6
  7. Crystal structure of ethyl 1-benzyl-5-phenyl-1H-pyrazole-3-carboxylate, C19H18N2O2
  8. Crystal structure of 2-(1-benzyl-3-phenyl-1H-pyrazol-5-yl)-5-(4-nitrobenzylthio)-1,3,4-oxadiazole, C25H19N5O3S
  9. Structure and photochromism of 1,2-bis[2-methyl-5-(2-chlorophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C27H16Cl2F6S2
  10. The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-4-ylmethylene)aniline, C18H22N2
  11. Crystal structure of (E)-2,4-dibromo-6-(((4-methyl-2-nitrophenyl)imino) methyl)phenol, C10H14Br2N2O3
  12. Crystal structure of (bis(2,2′-bipyridine-κ2N,N′))-(3,5-dinitrosalicylato-κ2O,O′)nickel(II), C27H18N6NiO7
  13. Crystal structure of 1-(diethoxy phosphonomethyl) 2-benzoyl-3-chloro-2-cyclohexen-1-ol, C18H24ClO5P
  14. Crystal structure of tetraaqua-bis(1,3-benzimidazol-3-ium-1,3-diacetato-κO)copper(II) hemihydrate, C22H27CuN4O12.50
  15. Crystal structure of 1α,11-dihydroxyeremophil-9-en-8-one, C15H24O3
  16. Crystal structure of 1-ferrocenylsulfonyl-1H-imidazo[4,5-b]pyridine, C16H13FeN3O2S
  17. Crystal structure of bis(μ2-azido-κ2N:N)-dichlorido-bis(μ2-2-(pyridin-2-yl)ethan-1-ol-κ2O,N)dicopper(II), C14H18Cl2Cu2N8O2
  18. Crystal structure of (5,15-cis-bis(2-hydroxy-1-naphthyl)-10-phenyl-20-(4-hydroxyphenyl)-porphyrinato)-(pyridine)-zinc(ii) pyridine solvate, C67H47N7O3Zn
  19. Crystal structure of (μ2-[2,2′-bis(diphenylphosphino)-1,1′-binaphthalene oxide-κ2O,P])-iodido copper(I), C44H32CuIOP2
  20. Crystal structure of 6,8-diphenyl-2-(4-fluorophenyl)-2,3-dihydroquinolin-4(3H)-one, C27H20FNO
  21. Crystal structure of 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetrahexoxycalix[4]arene, C68H104O4
  22. Crystal structure of N,N′–bis(pyridin-4-ylmethyl)pyrazine-2,3-dicarboxamide dihydrate, C18H20N6O4
  23. Crystal structure of a diaqua-bis(3,5-di(1H-imidazol-1-yl)pyridine-κN)-bis(2-(4-carboxy-phenyl)acetato-κO]manganese(II), C40H36MnN10O10
  24. Crystal structure of 4-(4-hydroxy-3-methoxy-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid methyl ester, C21H25NO5
  25. Crystal structure of (E)-4,4′-(ethene-1,2-diyl)bis(3-nitrobenzoic acid) 1.5 hydrate, C16H13N2O9.5
  26. Crystal structure of (E)-2-(5-(4-fluorophenyl)-3-(furan-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-5-((4-fluorophenyl)diazenyl)-4-methylthiazole, C23H17F2N5OS
  27. Crystal structure of the co-crystalline adduct 4-((4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide - acetic acid (1/1), C21H24N4O4S ⋅ C2H4O2
  28. Synthesis and crystal structure of 2-((5-chlorobenzo[c][1,2,5]thiadiazol-4-yl)amino)-4,5-dihydro-1H-imidazol-3-ium tetraphenylborate, C33H29BClN5S
  29. Crystal structure of (4-chlorophenyl)(3-ferrocenyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)methanone, C21H14ClF3FeN2O
  30. Crystal structure of (S)-benzyl 3-(benzylcarba-moyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate, C25H24N2O3
  31. Crystal structure of 5-acetyl-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one, C15H17FN2O4
  32. Crystal structure of 2-(4-fluorophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16FIN2
  33. Crystal structure of methyl 1H-indole-2-carboxylate, C10H9NO2
  34. Crystal structure of 2,3-diphenyl-1-[(dipropylamino)acetyl]-1,3-diazaspiro[4.5]decan-4-one, C28H37N3O2
  35. Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C13H12N2O3
  36. Crystal structure of 2,9-dibromo-1,10-phenanthroline, C12H6Br2N2
  37. Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C18H20FN3S
  38. Crystal structure of trans-bis((E)-7-oxo-4-(phenyldiazenyl)cyclohepta-1,3,5-trien-1-olato)-κ2O,O′)-bis(pyridine-κN)cobalt(II), C36H28CoN6O4
  39. Crystal structure of 2-(4-methyl-3-phenylthiazol-2(3H)-ylidene)malononitrile, C13H9N3S
  40. Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C24H27ClN2S
  41. Crystal structure of chlorido{[3-(η5-cyclopenta-dienyl)-2,2,3-trimethyl-1-phenylbutylidene] azanido-κN}[η2(N,O)-N,N-dimethylhydroxylaminato]titanium(IV), C20H27ClN2OTi
  42. Crystal Structure of 1,1′-dimethyl-[4,4′-bipyridine]-1,1′-diium tetrachloridozincate(II), C12H14Cl4N2Zn
  43. Crystal structure of 5-nitro-2-(pyrrolidin-1-yl)benzaldehyde, C11H12N2O3
  44. Crystal structure of 2,3-diphenyl-1-(morpholin-4-ylacetyl)-1,3-diazaspiro[4.5]decan-4-one, C26H31N3O3
  45. Crystal structure of 3,3-dimethyl-3,4-dihydro-1H-benzo[c]chromene-1,6(2H)-dione, C15H14O3
  46. Crystal structure of bis(2-(2-hydroxymethyl)pyridine-κ2N,O)-bis(pivalato-κO)nickel(II), C22H32N2NiO6
  47. Crystal structure of (1,10-phenanthroline-κ2N,N′)-bis(1H-pyrazole-3-carboxylato-κ2N,O)manganese(II) trihydrate, C20H20N6O7Mn
  48. The crystal structure of 3-aminopropan-1-aminium iodide, C3H11N2I
  49. Crystal structure of ethyl 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4 carboxylate, C12H12ClN3O2
  50. Crystal structure of 4,4′-((1Z,1′Z)-2,2′-(2,5-diethoxy-1,4-phenylene)bis(ethene-2,1-diyl))dipyridine, C24H24N2O2
  51. Crystal structure of (16S)-12,16-epoxy-11,14-dihydroxy-17(15/16)-abeo-3a,18-cyclo-8,11,13-abietatrien-7-one, C20H24O4
  52. Crystal structure of aquadichlorido(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ3N,N′,N′′)nickel(II) monohydrate, C18H16Cl2N6NiO2
  53. Crystal structure of catena-poly[dichlorido-(μ-ethane-1,2-diyl-bis-(pyridyl-4-carboxylate-κN:N′)mercury(II)], C15H14Cl2HgN2O4
  54. Crystal structure of methyl 2-acetamido-5-chlorbenzoate, C10H10ClNO3
  55. Crystal structure of tetrakis(μ2-3,3-dimethylacrylato-κ2O,O′)-bis(2-aminopyrimidine-κN) dicopper(II), C28H38Cu2N6O8
  56. Crystal structure of 3-amino-8-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2
  57. Crystal structure of 4-(2-ammonioethyl)morpholin-4-ium dichloride monohydrate, C6H18Cl2N2O2
  58. Crystal structure of 1-(3-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone O-benzyl oxime, C22H19BrN2O2
  59. Crystal structure of 2-(4-(dimethylamino)-2-fluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol monohydrate, C15H20FN7O2
  60. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
  61. Crystal structure of 1,2,3,4,5-pentamethyl-1,3-cyclopentadiene, C10H16
https://doi.org/10.1515/ncrs-2016-0305
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of 2,5-diiodo-4-nitro-1H-imidazole hemihydrate, C6H4I4N6O5
  3. Crystal structure of catena-poly[μ2-2,2′-(1,3-phenylene)diacetato-κ4O,O′:O′′,O′′′)-(μ2-1,6-bis(2-methyl-1H-benzo[d]imidazol-1-yl)hexane-κ2N:N′)cadmium(II)], C32H34CdN4O4
  4. Crystal structure of poly[aqua-(2,2′-bipyridine-κN,N′)-(μ4-5,5′-(hexane-1,6-diyl)-bis(oxy)diisophthalato κ8O1,O2:O3,O4:O5,O6:O7,O8)manganese(II)], C21H21MnN2O7
  5. Crystal structure of poly-[(μ2-((1,3-bis(benzimidazol-1-yl)propane-κ2N:N′)(μ2-4-tert-butyl-phthalato-κ2O:O′)cobalt(II)] monohydrate, C29H30CoN4O5
  6. Crystal structure of 2-amino-4-(3,4,5-trimethoxy-phenyl)-5-(oxo-5,6,7,8-tetrahydro-4H-chromene)-3-carbonitrile – ethanol (1/1), C21H26N2O6
  7. Crystal structure of ethyl 1-benzyl-5-phenyl-1H-pyrazole-3-carboxylate, C19H18N2O2
  8. Crystal structure of 2-(1-benzyl-3-phenyl-1H-pyrazol-5-yl)-5-(4-nitrobenzylthio)-1,3,4-oxadiazole, C25H19N5O3S
  9. Structure and photochromism of 1,2-bis[2-methyl-5-(2-chlorophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C27H16Cl2F6S2
  10. The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-4-ylmethylene)aniline, C18H22N2
  11. Crystal structure of (E)-2,4-dibromo-6-(((4-methyl-2-nitrophenyl)imino) methyl)phenol, C10H14Br2N2O3
  12. Crystal structure of (bis(2,2′-bipyridine-κ2N,N′))-(3,5-dinitrosalicylato-κ2O,O′)nickel(II), C27H18N6NiO7
  13. Crystal structure of 1-(diethoxy phosphonomethyl) 2-benzoyl-3-chloro-2-cyclohexen-1-ol, C18H24ClO5P
  14. Crystal structure of tetraaqua-bis(1,3-benzimidazol-3-ium-1,3-diacetato-κO)copper(II) hemihydrate, C22H27CuN4O12.50
  15. Crystal structure of 1α,11-dihydroxyeremophil-9-en-8-one, C15H24O3
  16. Crystal structure of 1-ferrocenylsulfonyl-1H-imidazo[4,5-b]pyridine, C16H13FeN3O2S
  17. Crystal structure of bis(μ2-azido-κ2N:N)-dichlorido-bis(μ2-2-(pyridin-2-yl)ethan-1-ol-κ2O,N)dicopper(II), C14H18Cl2Cu2N8O2
  18. Crystal structure of (5,15-cis-bis(2-hydroxy-1-naphthyl)-10-phenyl-20-(4-hydroxyphenyl)-porphyrinato)-(pyridine)-zinc(ii) pyridine solvate, C67H47N7O3Zn
  19. Crystal structure of (μ2-[2,2′-bis(diphenylphosphino)-1,1′-binaphthalene oxide-κ2O,P])-iodido copper(I), C44H32CuIOP2
  20. Crystal structure of 6,8-diphenyl-2-(4-fluorophenyl)-2,3-dihydroquinolin-4(3H)-one, C27H20FNO
  21. Crystal structure of 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetrahexoxycalix[4]arene, C68H104O4
  22. Crystal structure of N,N′–bis(pyridin-4-ylmethyl)pyrazine-2,3-dicarboxamide dihydrate, C18H20N6O4
  23. Crystal structure of a diaqua-bis(3,5-di(1H-imidazol-1-yl)pyridine-κN)-bis(2-(4-carboxy-phenyl)acetato-κO]manganese(II), C40H36MnN10O10
  24. Crystal structure of 4-(4-hydroxy-3-methoxy-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid methyl ester, C21H25NO5
  25. Crystal structure of (E)-4,4′-(ethene-1,2-diyl)bis(3-nitrobenzoic acid) 1.5 hydrate, C16H13N2O9.5
  26. Crystal structure of (E)-2-(5-(4-fluorophenyl)-3-(furan-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-5-((4-fluorophenyl)diazenyl)-4-methylthiazole, C23H17F2N5OS
  27. Crystal structure of the co-crystalline adduct 4-((4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide - acetic acid (1/1), C21H24N4O4S ⋅ C2H4O2
  28. Synthesis and crystal structure of 2-((5-chlorobenzo[c][1,2,5]thiadiazol-4-yl)amino)-4,5-dihydro-1H-imidazol-3-ium tetraphenylborate, C33H29BClN5S
  29. Crystal structure of (4-chlorophenyl)(3-ferrocenyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)methanone, C21H14ClF3FeN2O
  30. Crystal structure of (S)-benzyl 3-(benzylcarba-moyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate, C25H24N2O3
  31. Crystal structure of 5-acetyl-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one, C15H17FN2O4
  32. Crystal structure of 2-(4-fluorophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16FIN2
  33. Crystal structure of methyl 1H-indole-2-carboxylate, C10H9NO2
  34. Crystal structure of 2,3-diphenyl-1-[(dipropylamino)acetyl]-1,3-diazaspiro[4.5]decan-4-one, C28H37N3O2
  35. Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C13H12N2O3
  36. Crystal structure of 2,9-dibromo-1,10-phenanthroline, C12H6Br2N2
  37. Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C18H20FN3S
  38. Crystal structure of trans-bis((E)-7-oxo-4-(phenyldiazenyl)cyclohepta-1,3,5-trien-1-olato)-κ2O,O′)-bis(pyridine-κN)cobalt(II), C36H28CoN6O4
  39. Crystal structure of 2-(4-methyl-3-phenylthiazol-2(3H)-ylidene)malononitrile, C13H9N3S
  40. Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C24H27ClN2S
  41. Crystal structure of chlorido{[3-(η5-cyclopenta-dienyl)-2,2,3-trimethyl-1-phenylbutylidene] azanido-κN}[η2(N,O)-N,N-dimethylhydroxylaminato]titanium(IV), C20H27ClN2OTi
  42. Crystal Structure of 1,1′-dimethyl-[4,4′-bipyridine]-1,1′-diium tetrachloridozincate(II), C12H14Cl4N2Zn
  43. Crystal structure of 5-nitro-2-(pyrrolidin-1-yl)benzaldehyde, C11H12N2O3
  44. Crystal structure of 2,3-diphenyl-1-(morpholin-4-ylacetyl)-1,3-diazaspiro[4.5]decan-4-one, C26H31N3O3
  45. Crystal structure of 3,3-dimethyl-3,4-dihydro-1H-benzo[c]chromene-1,6(2H)-dione, C15H14O3
  46. Crystal structure of bis(2-(2-hydroxymethyl)pyridine-κ2N,O)-bis(pivalato-κO)nickel(II), C22H32N2NiO6
  47. Crystal structure of (1,10-phenanthroline-κ2N,N′)-bis(1H-pyrazole-3-carboxylato-κ2N,O)manganese(II) trihydrate, C20H20N6O7Mn
  48. The crystal structure of 3-aminopropan-1-aminium iodide, C3H11N2I
  49. Crystal structure of ethyl 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4 carboxylate, C12H12ClN3O2
  50. Crystal structure of 4,4′-((1Z,1′Z)-2,2′-(2,5-diethoxy-1,4-phenylene)bis(ethene-2,1-diyl))dipyridine, C24H24N2O2
  51. Crystal structure of (16S)-12,16-epoxy-11,14-dihydroxy-17(15/16)-abeo-3a,18-cyclo-8,11,13-abietatrien-7-one, C20H24O4
  52. Crystal structure of aquadichlorido(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ3N,N′,N′′)nickel(II) monohydrate, C18H16Cl2N6NiO2
  53. Crystal structure of catena-poly[dichlorido-(μ-ethane-1,2-diyl-bis-(pyridyl-4-carboxylate-κN:N′)mercury(II)], C15H14Cl2HgN2O4
  54. Crystal structure of methyl 2-acetamido-5-chlorbenzoate, C10H10ClNO3
  55. Crystal structure of tetrakis(μ2-3,3-dimethylacrylato-κ2O,O′)-bis(2-aminopyrimidine-κN) dicopper(II), C28H38Cu2N6O8
  56. Crystal structure of 3-amino-8-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2
  57. Crystal structure of 4-(2-ammonioethyl)morpholin-4-ium dichloride monohydrate, C6H18Cl2N2O2
  58. Crystal structure of 1-(3-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone O-benzyl oxime, C22H19BrN2O2
  59. Crystal structure of 2-(4-(dimethylamino)-2-fluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol monohydrate, C15H20FN7O2
  60. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
  61. Crystal structure of 1,2,3,4,5-pentamethyl-1,3-cyclopentadiene, C10H16
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