Home Physical Sciences 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
Article Open Access

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

  • Rui-Xia Qiu , Guo-Qiang Li , Hong-Ji Chen , Lin Wang and Chun-Hua Wang EMAIL logo
Published/Copyright: October 8, 2016
Download Article (PDF)
Become an author with De Gruyter Brill
Submit Manuscript Author Information
Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 232 Issue 1

Abstract

C21H24N2O3, orthorhombic, P212121 (no. 19), a = 9.7186(12) Å, b = 13.4479(16) Å, c = 13.6679(17) Å, V = 1786.3(4) Å3, Z = 4, Rgt(F) = 0.0393, wRref(F2) = 0.0937, T = 173 K.

CCDC no.:: 1503912

The asymmetric unit of the tilte crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Colourless needle Size 0.46 × 0.43 × 0.42 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.9 cm−1
Diffractometer, scan mode:Bruker SMART, ω
2θmax, completeness:54.2°, >99%
N(hkl)measured, N(hkl)unique, Rint:10249, 3922, 0.018
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3592
N(param)refined:237
Programs:Bruker programs [7], SHELX [8], OLEX2 [9]
Table 2

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

AtomxyzUiso*/Ueq
C10.4940(2)0.29914(15)0.25706(15)0.0277(4)
C20.6346(2)0.31259(18)0.26874(16)0.0335(5)
H20.68080.36740.23970.040*
C30.7059(2)0.24262(19)0.32472(16)0.0358(5)
H30.80250.24930.33300.043*
C40.6380(2)0.16362(17)0.36840(16)0.0342(5)
H40.68850.11640.40550.041*
C50.4958(2)0.15295(15)0.35829(15)0.0293(4)
H50.44910.09960.38950.035*
C60.4241(2)0.22061(14)0.30251(14)0.0255(4)
C70.27161(19)0.23440(14)0.28302(14)0.0234(4)
C80.2756(2)0.30714(14)0.19794(14)0.0239(4)
C90.1748(2)0.31335(14)0.12948(14)0.0243(4)
C100.0598(2)0.23769(14)0.13498(15)0.0245(4)
H10A0.01180.23410.07120.029*
H10B−0.00780.25820.18530.029*
C110.1197(2)0.13424(15)0.16134(15)0.0257(4)
C120.18175(19)0.14042(14)0.26462(15)0.0252(4)
H120.23690.07920.27830.030*
C130.2029(2)0.28330(15)0.37573(15)0.0297(4)
H13A0.27320.31110.42040.036*
H13B0.13800.33660.35670.036*
C140.1278(2)0.19643(17)0.42266(16)0.0330(5)
H14A0.19170.15170.45790.040*
H14B0.05480.21920.46790.040*
C15−0.0045(2)0.05744(17)0.35023(18)0.0364(5)
H15A−0.08360.06910.39440.044*
H15B0.05620.00720.38090.044*
C16−0.0549(2)0.01968(16)0.25342(19)0.0367(5)
H16−0.1535−0.00160.25080.044*
C170.0035(2)0.05829(15)0.16209(19)0.0342(5)
H17−0.05990.05980.10450.041*
C180.2303(2)0.10004(16)0.08803(16)0.0315(5)
H18A0.31280.14240.09630.038*
H18B0.25710.03090.10410.038*
C190.1859(3)0.1039(2)−0.01941(18)0.0459(6)
H19A0.25900.0762−0.06060.069*
H19B0.16860.1730−0.03830.069*
H19C0.10160.0648−0.02810.069*
C200.1935(2)0.38065(14)0.04768(15)0.0246(4)
C210.1084(3)0.4374(2)−0.10497(16)0.0412(6)
H21A0.02510.4337−0.14520.062*
H21B0.18760.4150−0.14340.062*
H21C0.12310.5063−0.08400.062*
N10.40036(18)0.35554(13)0.20148(13)0.0290(4)
H10.41870.41290.17330.035*
N20.07076(18)0.14928(13)0.33618(13)0.0298(4)
O10.29034(15)0.43840(11)0.03840(11)0.0315(3)
O20.09263(15)0.37451(11)−0.02002(10)0.0303(3)
O30.04108(18)−0.03961(11)0.19778(14)0.0434(4)

Source of material

The Catharanthus roseus was purchased from Vinca Pharmaceutical Co., Ltd. HaiNan, China. The powdered twigs and leaves of C. roseus (8.5 kg) were extracted with 95% ethanol. The solution was evaporated in vacuum to get a residue (1234 g). The residue was dissolved in water to form a suspension and then adjusted to pH 6 with diluted (3%) H2SO4. The acidic suspension was partitioned with CHCl3. The aqueous phase was basified with an ammonia solution (2%) to pH 8 and then extracted with CHCl3 to obtain the raw alkaloid (105 g), which was subjected to silica gel column chromatography (8 × 150 cm, 1000 g) eluting with a gradient of CHCl3-CH3OH (100:0, 99:1, 98:2, 96:4, 93:7, 90:10, 85:15, 80:20, 70:30, 0:100, each 10 L to give twenty fractions. Fraction 3 (2.72 g) was subjected to silica gel column chromatography (4 × 80 cm, 250 g) [eluted with n-hexane-EtOAc (9:1, 8:2, 7:3, 5:5, each 1 L)] to afford eight subfractions (3-1~3-8). Subfraction 3-4 (346 mg) was purified by silica gel column chromatography (2 × 60 cm, 40 g) [eluted with CHCl3-CH3OH (100:0, 99:1, 98:2, 95:5, each 400 mL)] to afford the pure title compound.

Experimental details

The C-bound H atoms were positioned geometrically and were included in the refinement in the riding-model approximation. The crystal structure was solved by direct method and refined by full-matrix least-squares refinement with SHELX program [8].

Discussion

Catharanthus roseus is a member of the family Apocynaceae. It is a well-known medicinal plant because of its anti-tumor activity. Up to now more than one hundred alkaloids have been isolated from the plant and most of them are indole alkaloids. In our study on Catharanthus roseus, we have obtained lochnericine. Lochnericine has also been isolated from Amsonia angustifolia [1], Vinca pusilla [2], Alstonia lanceolata [3], Tabernaemontana citrifolia [4], Amsonia sinensis [5]. The title compound is composed of one benzo moiety, two five-membered rings and two six-membered rings. The atoms C9, C20, C21, O1, O2 are coplanar (mean deviation 0.0115). The atoms C7, C8, C9, C10 form another plane (mean deviation 0.0177 Å). The dihedral angle between the benzo moiety and the methyl ester group is 30.30(7)°, while it is 20.55(9)° between the benzo moiety and the plane defined by C7, C8, C9, C10. The distance between C8 and C9 is 1.357(2) Å, which is within the normal range of double bond. The five-membered ring A[N1, C1, C6, C7, C8] adopts a half chair conformation, while the ring B [N2, C12, C7, C13, C14] adopts a envelope conformation with the puckering parameters [6] Q = 0.215(2) Å, φ = 307.76(61)° and Q = 0.445(3) Å, φ = 329.61(82)°, respectively. The six-membered ring C [N2, C12, C11, C17, C16, C15] adopts a half chair conformation with the puckering parameters Q = 0.53(19) Å, θ = 127.8(3)°, φ = 208.66(27)° and ring D [C7, C8, C9, C10, C11, C12] adopts a screw-boat conformation with the puckering parameters Q = 0.58(55) Å, θ = 67.7(7)°, φ = 214.61(47)°. There is an intramolecular hydrogen bond N1-H1⋯O1.

Acknowledgements:

This work was supported financially by the Fundamental Research Funds for the Central Universities (Grant 11615305),Tianjin Applied Basic and Cutting-edge Technology Research Program (Nos.13JCZDJC28600).

References

1. Clauder, O.; Kocsis, A.; Bojthe-Horvath, K.; Mathe, I.; Tamas, J.: Alkaloid of amsoniaangustifolia. I. Acta Chim. Acad. Sci. Hung. 75 (1973) 423–425.Search in Google Scholar

2. Patra, A.; Mukhopadhyay, A. K.; Mitra, A. K.: Alkaloids of vincapusilla: isolation of lochnericine, vindorosine and venoterpine. Indian J. Chem. 17B (1979) 175–176.10.1002/chin.197949332Search in Google Scholar

3. Vercauteren, J.; Massiot, G. ; Sevenet, T.; Richard, B.; Lobjois, V.; Le, M.L.; Levy, J.: Plants from New Caledonia. Alkaloids of alstonialanceolata. Phytochemistry 20 (1981) 1411–1413.10.1016/0031-9422(81)80050-7Search in Google Scholar

4. Kutney, J. P.; Perez, I.: Studies on natural products from Cuban plants. Alkaloids from tabernaemontanacitrifolia. Helv. Chim. Acta 65 (1982) 2242–2250.10.1002/hlca.19820650729Search in Google Scholar

5. Liu, H. M.; Wu, B.; Zheng, Q. T.; Feng, X. Z.: New indolealkaloild from amsoniasinensis. Planta Med. 57 (1991) 566–568.10.1055/s-2006-960207Search in Google Scholar PubMed

6. Cremer, D.; Pople, J. A.: General definition of ring puckering coordinates. J. Am. Chem. Soc. 97 (1975) 1354–1358.10.1021/ja00839a011Search in Google Scholar

7. Bruker: SAINT-Plus, SHELXTL and SADABS. Bruker AXS Inc., Madison, Wi, USA, (2004).Search in Google Scholar

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

9. 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) 339–341.10.1107/S0021889808042726Search in Google Scholar

Received: 2016-4-19
Accepted: 2016-9-14
Published Online: 2016-10-8
Published in Print: 2017-1-1

©2016 Rui-Xia Qiu et al., published by De Gruyter.

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

Articles in the same Issue

  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
  39. Crystal structure of (E)-1-(2-(thiophen-2-ylmethylene)hydrazinyl)phthalazine hydrochloride–ethanol (1/1), C15H17ClN4OS
  40. Crystal structure of N,N-diethyl-5-bromo-3,4-dihydro-2,4-dioxopyrimidine-1(2H)-carboxamide, C9H12BrN3O3
  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
  44. Crystal structure of 4-(3,4-dimethyl-phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester, C21H25NO3
  45. Crystal structure of (E)-2-({4-hydroxy-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]phenyl} methylidene)-1-indanone, C23H26N2O3
  46. Crystal structure of tripropylammonium 2′-carboxy-[1,1′-biphenyl]-2-carboxylate – [1,1′-biphenyl]-2,2′-dicarboxylic acid (2/1), C60H72N2O12
  47. Crystal structure of catena-poly-{aqua-[μ2-1,2-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′]-[μ2-4,4′-(dimethylsilanediyl)dibenzato-κ3O,O′:O′]nickel(II)}, C30H30N4NiO5Si
  48. The crystal structure of 1-(4-bromophenyl)-2-(4-(4-fluorophenyl)piperazin-1-yl)ethanol, C18H20BrFN2O1
  49. Crystal structure of trimethylammonium 4-((4-carboxyphenyl)sulfonyl)benzoate, C17H19NO6S
  50. Crystal structure of syn-2,4-di-o-tolylpentane-2,4-diol, C19H24O2
  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
  54. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanopalladate(II), C14H24N8Pd2
  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
https://doi.org/10.1515/ncrs-2016-0129
Creative Commons
BY-NC-ND 3.0

Articles in the same Issue

  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
  39. Crystal structure of (E)-1-(2-(thiophen-2-ylmethylene)hydrazinyl)phthalazine hydrochloride–ethanol (1/1), C15H17ClN4OS
  40. Crystal structure of N,N-diethyl-5-bromo-3,4-dihydro-2,4-dioxopyrimidine-1(2H)-carboxamide, C9H12BrN3O3
  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
  44. Crystal structure of 4-(3,4-dimethyl-phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester, C21H25NO3
  45. Crystal structure of (E)-2-({4-hydroxy-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]phenyl} methylidene)-1-indanone, C23H26N2O3
  46. Crystal structure of tripropylammonium 2′-carboxy-[1,1′-biphenyl]-2-carboxylate – [1,1′-biphenyl]-2,2′-dicarboxylic acid (2/1), C60H72N2O12
  47. Crystal structure of catena-poly-{aqua-[μ2-1,2-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′]-[μ2-4,4′-(dimethylsilanediyl)dibenzato-κ3O,O′:O′]nickel(II)}, C30H30N4NiO5Si
  48. The crystal structure of 1-(4-bromophenyl)-2-(4-(4-fluorophenyl)piperazin-1-yl)ethanol, C18H20BrFN2O1
  49. Crystal structure of trimethylammonium 4-((4-carboxyphenyl)sulfonyl)benzoate, C17H19NO6S
  50. Crystal structure of syn-2,4-di-o-tolylpentane-2,4-diol, C19H24O2
  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
  54. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanopalladate(II), C14H24N8Pd2
  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
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2026 De Gruyter Brill
Downloaded on 21.1.2026 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2016-0129/html
Scroll to top button