Startseite Naturwissenschaften Crystal structure of 1-(diethoxy phosphonomethyl) 2-benzoyl-3-chloro-2-cyclohexen-1-ol, C18H24ClO5P
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Crystal structure of 1-(diethoxy phosphonomethyl) 2-benzoyl-3-chloro-2-cyclohexen-1-ol, C18H24ClO5P

  • Marole M. Maluleka und Malose J. Mphahlele EMAIL logo
Veröffentlicht/Copyright: 17. März 2017
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 232 Heft 3

Abstract

C18H24ClO5P, triclinic, P1̅ (no. 2), a = 11.5140(14) Å, b = 11.5358(15) Å, c = 15.582(2) Å, α = 76.106(2)°, β = 77.556(2)°, γ = 74.783(3)°, V = 1912.8(4)Å3, Z = 4, Rgt(F) = 0.0481, wRref(F2) = 0.1313, T = 173(2) K.

CCDC no.:: 242998

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:Colorless prism
Size:0.40 × 0.30 × 0.15 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:3.1 cm−1
Diffractometer, scan mode:Bruker SMART, φ and ω
2θmax, completeness:50°, >99%
N(hkl)measured, N(hkl)unique, Rint:10499, 6692, 0.026
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 5210
N(param)refined:497
Programs:Bruker programs [1, 3] , SADABS [2], Platon [4]
Table 2

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

AtomxyzUiso*/Ueq
Cl11.03058(7)0.81968(8)0.30756(6)0.0453(2)
O10.78757(19)1.0592(2)0.20686(13)0.0431(5)
O20.60668(17)1.03214(17)0.41117(13)0.0289(4)
H10.620(3)1.025(3)0.462(2)0.039(9)*
O30.35600(18)0.9756(2)0.42174(13)0.0390(5)
O40.42857(19)0.7713(2)0.37031(15)0.0441(5)
O50.37216(19)0.9643(2)0.25892(13)0.0451(6)
P10.42617(7)0.91247(7)0.34881(5)0.03158(19)
C10.8757(2)1.1090(2)0.31327(18)0.0281(6)
C20.9190(3)1.2041(3)0.2512(2)0.0367(7)
H20.90811.21840.19050.044*
C30.9775(3)1.2776(3)0.2773(2)0.0429(8)
H31.00701.34160.23460.051*
C40.9926(3)1.2573(3)0.3658(2)0.0424(8)
H41.03311.30720.38380.051*
C50.9492(3)1.1648(3)0.4279(2)0.0380(7)
H50.95911.15200.48870.046*
C60.8909(2)1.0899(3)0.40233(18)0.0311(6)
H60.86161.02610.44540.037*
C70.8161(2)1.0308(3)0.28143(17)0.0285(6)
C80.7910(2)0.9139(2)0.34242(17)0.0261(6)
C90.8790(2)0.8147(3)0.35722(19)0.0313(6)
C100.8641(3)0.6936(3)0.4145(2)0.0410(7)
H10A0.90050.67970.46920.049*
H10B0.90780.62740.38120.049*
C110.7299(3)0.6895(3)0.4407(2)0.0413(7)
H11A0.71980.62150.49240.050*
H11B0.70110.67360.39010.050*
C120.6526(3)0.8103(3)0.46569(18)0.0338(6)
H12A0.56700.80270.48710.041*
H12B0.68300.82740.51510.041*
C130.6572(2)0.9165(2)0.38572(17)0.0263(6)
C140.5851(2)0.9142(3)0.31363(17)0.0290(6)
H14A0.62560.84080.28720.035*
H14B0.59170.98680.26540.035*
C150.3125(4)0.7355(4)0.4116(3)0.0727(12)
H15A0.29300.74420.47510.087*
H15B0.24620.79080.38040.087*
C160.3190(4)0.6118(4)0.4066(3)0.0748(13)
H16A0.34410.60180.34410.112*
H16B0.23870.59240.42960.112*
H16C0.37860.55640.44270.112*
C170.2574(3)1.0520(4)0.2536(2)0.0527(9)
H17A0.25031.11460.28930.063*
H17B0.18911.01010.27840.063*
C180.2510(4)1.1109(4)0.1596(2)0.0668(12)
H18A0.31921.15170.13520.100*
H18B0.17381.17160.15590.100*
H18C0.25591.04890.12490.100*
Cl1A1.32032(7)0.72983(7)0.15285(6)0.0423(2)
O1A1.12185(18)0.50762(19)0.28351(13)0.0371(5)
O2A1.05677(18)0.48866(17)0.08935(13)0.0290(4)
H1A1.105(3)0.478(3)0.043(3)0.056(11)*
O3A0.78414(19)0.5752(2)0.06055(16)0.0533(7)
O4Aa0.7399(3)0.7731(2)0.1049(3)0.0454(11)
O4Bb0.6684(3)0.7317(3)0.1629(2)0.0370(15)
P1A0.78278(7)0.62847(7)0.13530(5)0.0347(2)
C1A1.3059(2)0.4317(2)0.19283(18)0.0295(6)
C2A1.3536(3)0.3493(3)0.2649(2)0.0397(7)
H2A1.30990.35000.32400.048*
C3A1.4640(3)0.2666(3)0.2510(2)0.0489(9)
H3A1.49640.21130.30050.059*
C4A1.5268(3)0.2646(3)0.1651(3)0.0502(9)
H4A1.60280.20810.15570.060*
C5A1.4802(3)0.3442(3)0.0926(2)0.0440(8)
H5A1.52310.34110.03360.053*
O5Aa0.6929(3)0.5995(3)0.22647(18)0.0511(12)
O5Bb0.7742(4)0.5107(4)0.2121(3)0.060(2)
C6A1.3702(3)0.4287(3)0.1062(2)0.0349(7)
H6A1.33890.48450.05650.042*
C7A1.1878(2)0.5194(2)0.21040(18)0.0277(6)
C8A1.1467(2)0.6242(2)0.13589(17)0.0245(6)
C9A1.1967(2)0.7207(3)0.10722(19)0.0294(6)
C10A1.1584(3)0.8301(3)0.0367(2)0.0373(7)
H10C1.22280.8305−0.01690.045*
H10D1.14890.90560.05950.045*
C11A1.0387(3)0.8293(3)0.0105(2)0.0379(7)
H11C1.03000.8839−0.04850.045*
H11D0.96970.86100.05510.045*
C12A1.0341(3)0.6995(2)0.00547(18)0.0292(6)
H12C0.95790.7023−0.01540.035*
H12D1.10370.6676−0.03870.035*
C13A1.0395(2)0.6133(2)0.09632(17)0.0250(6)
C14A0.9216(2)0.6385(3)0.16439(19)0.0336(7)
H14C0.91040.72180.17590.040*
H14D0.93380.58020.22140.040*
C15Aa0.6118(3)0.8303(3)0.0940(2)0.0491(9)
H15Ca0.55660.80970.15090.059*
H15Da0.58940.80000.04690.059*
C15Bb0.6118(3)0.8303(3)0.0940(2)0.0491(9)
H15Eb0.52570.86420.11790.059*
H15Fb0.61350.79760.04050.059*
C16Aa0.6003(5)0.9663(3)0.0682(4)0.0441(14)
H16Da0.51581.00680.06110.066*
H16Ea0.65450.98580.01160.066*
H16Fa0.62300.99520.11520.066*
C16Bb0.6830(8)0.9282(7)0.0697(5)0.059(3)
H16Gb0.64750.99460.02400.088*
H16Hb0.76790.89380.04610.088*
H16Ib0.68020.96040.12310.088*
C17Aa0.6375(10)0.4924(10)0.2437(3)0.082(2)
H17Ca0.68440.43470.20410.098*
H17Da0.55260.51910.23150.098*
C17Bb0.6575(13)0.4704(19)0.2400(3)0.082(2)
H17Eb0.66040.40140.21150.098*
H17Fb0.58940.53860.22160.098*
C18Aa0.6389(4)0.4309(4)0.3399(2)0.0753(13)
H18Da0.59820.36230.35380.113*
H18Ea0.59600.48990.37850.113*
H18Fa0.72350.40020.35040.113*
C18Bb0.6389(4)0.4309(4)0.3399(2)0.0753(13)
H18Gb0.59720.36280.35740.113*
H18Hb0.58920.49970.36740.113*
H18Ib0.71820.40430.36030.113*

  1. aOccupancy: 0.604(4); bOccupancy: 0.396(4).

Source of material

To a stirred solution of n-butyl lithium (1.6 M solution in hexane; 5.4 mL, 8.7 mmol) in THF (30 mL) at −65 °C was added dropwise with stirring a solution of diethyl methylphosphonate (1.22 g, 8.0 mmol) in THF (1 mL). The mixture was stirred at −65 °C for 30 min, and a solution of 2-benzoyl-3-chlorocyclohex-2-enone (1.89 g, 8.0 mmol) in THF (5 mL) was added. After 15 min at −65 °C, the mixture was allowed to warm up to room temperature and was then stirred for 1 h at this temperature. The mixture was quenched with saturated aqueous ammonium chloride and extracted with chloroform (3 × 30 mL). The chloroform extract was washed with water (2 × 20 mL), dried (MgS04), and filtered, and the solvent was removed under reduced pressure. The residue was purified by column chromatography to afford the title compound as a colorless solid (1.71 g, 55%), 88–90 °C (1:3 EtOAc-Pet. ether, v/v). Infrared spectrum: υmax: (ATR) 1265 (P = O), 1580 (C = C), 1658 (C = O) and 3267 (OH); 1H-NMR (300 MHz, CDCl3) 1.29 (3H, t, J 7.2 Hz, 1 × CH3 of POEt), 1.31 (3H, t, J 7.2 Hz, 1 × CH3 of POEt), 1.78 (1H, m, 1 × H of CH2), 2.01–2.18 (2H, m, 1 × H of 2 × CH2), 2.21 (1H, d, J 15.9 Hz, 1 × H of CH2P), 2.27 (1H, d, J 15.9 Hz, 1 × H of CH2P), 2.36–2.64 (3H, m, 1 × H of CH2 and CH2), 4.06 (4H, m, 2 × CH2 of POEt), 4.54 (1H, br s, OH), 7.45 (2H, dt, J 1.5 and 7.1 Hz, 3′-H and 5′-H), 7.56 (1H, tt, J 1.2 and 7.2 Hz, 4′-H) and 7.99 (2H, dd, J 1.2 and 8.4 Hz, 2′-H and 6′-H); 13C-NMR (75.0 MHz, CDCl3) 16.3 (dd, JCP 2.7 and 6.2Hz, CH3 of POEt), 19.7 (s, CH2), 33.0 (s, CH2), 35.5 (s, CH2), 34.7 (d, JCP 135.3 Hz, CH2P), 35.6 (s, CH2), 61.5 (d, JCP 7.0 Hz, 1 × CH2 of POEt), 62.3 (d, JCP 6.1 Hz, 1 × CH2 of POEt), 72.0 (d, JCP 2.7 Hz, C-1), 128.5 (s, C-3’ and C-5’), 129.8 (s, C-2’ and C-6’), 133.5 (s, C-4′), 133.6 (d, JCP 3.1 Hz, C-3), 136.7 (s, C-1′), 138.5 (d, JCP 16.7 Hz, C-2) and 196.7 (s, C = O); 31P-NMR (CDCl3) 29.40; HRMS (EI): found: 386.1049. C18H24O5ClP requires’ 386.1050. Crystals were obtained by recrystallization from 3:2 ethyl acetate-petroleum ether mixture.

Experimental details

Hydrogen atoms were located from the difference map then positioned geometrically and allowed to ride on their respective parent atoms. Hydrogen atoms involved in hydrogen bonding were located from the difference map and refined freely. Two ethoxy groups made up of atoms O4A, C15A and C16A and O5A, C17A and C18A were found to be disordered. These were refined over two positions with the final occupancies over the two positions being 0.604(4) and 0.396(4), respectively.

Discussion

Owing to the importance of cycloalkenones as chemical units in a large number of naturally occurring substances [5], development of new synthetic methods leading to substituted derivatives is currently one focal point in synthetic organic chemistry [6].

Lithiated diethyl alkylphosphonates react with 3-chlorocyclohex-2-en-1-ones substituted with a benzoyl group at the 2-position to afford the 1-(diethoxy phosphonomethyl) 2-benzoyl-3-chloro-2-cyclohexen-1-ol. This compound could be purified by column chromatography and its melting point determined without any signs of decomposition. The related adduct of trimethylsilylmagnesium bromide, on the other hand, previously fragmented spontaneously in situ to yield a diene [7], [8], [9].

The crystal structure contains two molecules in the asymmetric unit − one ordered and the other disordered around the ethoxy groups (cf. the figure). O-H⋯O = P intermolecular hydrogen bonding occurs between adjacent molecules forming a hydrogen bonded pair of centrosymetrically related molecules for both crystallographically independent molecules (graph set descriptor: R22(12)). Ordered molecules form hydrogen bonds exclusively to the other ordered molecules whereas disordered molecules form hydrogen bonds to the other disordered molecules.

Bond lengths and angles are all in the expected ranges.

Acknowledgement

The authors are grateful to the University of South Africa for financial assistance and M.A. Fernandes of Wits University for X-ray data.

References

1 Bruker SAINT+. Version 6.02 (includes XPREP and SADABS), Bruker AXS Inc., Madison, Wisconsin, USA, (1999).Suche in Google Scholar

2 Sheldrick, G. M.: SADABS. University of Göttingen, Germany, (1996).Suche in Google Scholar

3 Bruker. SHELXTL. Version 5.1. (includes XS, XL, XP, XSHELL) Bruker AXS Inc., Madison, Wisconsin, USA, (1999).Suche in Google Scholar

4 Spek, A.: Single-crystal structure validation with the program PLATON. J. Appl. Cryst. 36 (2003) 7–13.10.1107/S0021889802022112Suche in Google Scholar

5 Kim, J. H.; Lim, H. J.; Cheon, S. H.: A facile synthesis of (6S,1′S)-(+)-hernandulcin and (6S,1′R)-(+)-epihernandulcin. Tetrahedron 59 (2003) 7501–7507.10.1002/chin.200403179Suche in Google Scholar

6 Mphahlele, M. J.; Modro T. A.: Reaction of phosphonate-stabilized carbanions with cyclic enones bearing a β-leaving group. J. Org. Chem. 60 (1995) 8236–8240.10.1021/jo00130a024Suche in Google Scholar

7 Modro, A. M.; Modro, T. A.; Mphahlele, M. J.; Perlikowska, W.; Pienaar, A.; Sales, M.; van Rooyen, P. H.: Reaction of carbanions generated from arylmethylphosphonates with cyclic enones. regio- and stereoselectivity of addition. Can. J. Chem. 76 (1998) 1344–1352.10.1139/v98-180Suche in Google Scholar

8 Mphahlele, M. J.; Pienaar, A.; Modro, T. A.: Reactions of phosphorus-stabilized carbanions with cyclic enones. aromatization of the substitution and addition products. Perkin Trans. (1996) 1455–1460.10.1039/p29960001455Suche in Google Scholar

9 Tamura, Y.; Wada, A.; Sasho, M.; Kita, Y.: Reactions of 2-benzoyl-3-chloro-2-cyclohexen-1-ones with some organometallic compounds. Chem. Pharm. Bull. 31 (1983) 52–56.10.1248/cpb.31.52Suche in Google Scholar

Received: 2016-9-5
Accepted: 2017-2-16
Published Online: 2017-3-17
Published in Print: 2017-5-24

©2017 Marole M. Maluleka et al., published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  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-2016-0271
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Artikel in diesem Heft

  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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Heruntergeladen am 18.1.2026 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2016-0271/html?lang=de
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