Home The crystal structure of 4′-chloro-griseofulvin: (2S,6′R)-4′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-3′-ene-2′,3-dione, C16H14Cl2O5
Article Open Access

The crystal structure of 4′-chloro-griseofulvin: (2S,6′R)-4′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-3′-ene-2′,3-dione, C16H14Cl2O5

  • Kai-Ming Yang , Meng Zhang , Yi-Xiang Li , Liang-Zhu Huang , Yu Zhao , Hua Yang and Yu-Bin Bai ORCID logo EMAIL logo
Published/Copyright: May 31, 2024
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 239 Issue 4

Abstract

C16H14Cl2O5, orthorhombic, P212121 (no. 19), a = 8.6429 (4) Å, b = 11.3361 (6) Å, c = 33.9029 (11) Å, V = 3321.7 (3) Å3, Z = 8, R gt(F) = 0.0635, wR ref(F 2) = 0.1630, T = 293(2) K.

CCDC no.: 2211418

Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colourless block
Size: 0.20 × 0.12 × 0.10 mm
Wavelength: CuKα radiation (1.54184 Å)
μ: 3.72 mm−1
Diffractometer, scan mode: Xcalibur, ω
θ max, completeness: 71.8°, >99 %
N(hkl)measured, N(hkl)unique, R int: 12,583, 6346, 0.059
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 4807
N(param)refined: 421
Programs: Olex2, 1 Shelx 2 , 3
Table 2:

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

Atom x y z U iso*/U eq
C1 0.7618 (9) 0.1383 (8) 0.3599 (2) 0.0433 (18)
C2 0.6984 (10) 0.0542 (6) 0.3374 (2) 0.0418 (17)
H2 0.7121 −0.0246 0.3442 0.050*
C3 0.6085 (9) 0.0844 (6) 0.3026 (2) 0.0353 (15)
C4 0.6071 (7) 0.2147 (5) 0.29020 (16) 0.0263 (12)
C5 0.6117 (8) 0.2987 (6) 0.32557 (17) 0.0303 (14)
H5 0.5163 0.2865 0.3407 0.036*
C6 0.7481 (8) 0.2666 (7) 0.35274 (17) 0.0397 (16)
H6A 0.8434 0.2949 0.3409 0.048*
H6B 0.7352 0.3066 0.3778 0.048*
C7 0.7359 (7) 0.2306 (6) 0.25888 (15) 0.0255 (12)
C8 0.6547 (6) 0.2359 (5) 0.22156 (16) 0.0250 (11)
C9 0.7043 (6) 0.2406 (5) 0.18208 (15) 0.0237 (11)
C10 0.5948 (7) 0.2418 (6) 0.15252 (15) 0.0277 (12)
H10 0.6257 0.2438 0.1263 0.033*
C11 0.4374 (7) 0.2400 (6) 0.16190 (16) 0.0266 (12)
C12 0.3865 (6) 0.2385 (6) 0.20118 (16) 0.0263 (12)
C13 0.4968 (6) 0.2357 (5) 0.22964 (15) 0.0232 (11)
C14 0.6168 (11) 0.4274 (7) 0.3137 (2) 0.052 (2)
H14A 0.7102 0.4427 0.2993 0.077*
H14B 0.6143 0.4759 0.3369 0.077*
H14C 0.5290 0.4453 0.2974 0.077*
C15 0.9148 (7) 0.2482 (8) 0.13682 (16) 0.0387 (15)
H15A 0.8729 0.1839 0.1218 0.058*
H15B 1.0257 0.2437 0.1367 0.058*
H15C 0.8826 0.3216 0.1253 0.058*
C16 0.3673 (10) 0.2364 (11) 0.09365 (19) 0.073 (3)
H16A 0.2760 0.2324 0.0776 0.109*
H16B 0.4299 0.1677 0.0891 0.109*
H16C 0.4252 0.3058 0.0869 0.109*
C17 0.4577 (12) 0.5656 (8) 0.5052 (2) 0.059 (2)
C18 0.5663 (11) 0.5070 (9) 0.4868 (2) 0.058 (2)
H18 0.6688 0.5305 0.4898 0.070*
C19 0.5309 (10) 0.4057 (8) 0.46188 (19) 0.0463 (18)
C20 0.3603 (9) 0.3781 (6) 0.45557 (18) 0.0362 (16)
C21 0.2607 (10) 0.4071 (7) 0.4918 (2) 0.0460 (18)
H21 0.2939 0.3548 0.5132 0.055*
C22 0.2917 (11) 0.5347 (7) 0.5053 (2) 0.050 (2)
H22A 0.2368 0.5885 0.4880 0.060*
H22B 0.2510 0.5451 0.5317 0.060*
C23 0.3012 (9) 0.4436 (5) 0.41779 (17) 0.0324 (14)
C24 0.2640 (9) 0.3504 (5) 0.39048 (18) 0.0303 (15)
C25 0.2076 (8) 0.3504 (5) 0.35139 (17) 0.0270 (13)
C26 0.1856 (7) 0.2425 (5) 0.33266 (15) 0.0275 (11)
H26 0.1480 0.2408 0.3070 0.033*
C27 0.2196 (8) 0.1355 (6) 0.35205 (18) 0.0311 (14)
C28 0.2786 (9) 0.1352 (6) 0.39079 (19) 0.0360 (16)
C29 0.2964 (8) 0.2427 (6) 0.40859 (16) 0.0331 (13)
C30 0.0884 (12) 0.3836 (10) 0.4846 (3) 0.075 (3)
H30A 0.0506 0.4366 0.4647 0.112*
H30B 0.0320 0.3957 0.5087 0.112*
H30C 0.0747 0.3037 0.4759 0.112*
C31 0.1252 (11) 0.4599 (7) 0.2952 (2) 0.047 (2)
H31A 0.2041 0.4273 0.2785 0.070*
H31B 0.1058 0.5402 0.2877 0.070*
H31C 0.0319 0.4147 0.2924 0.070*
C32 0.1411 (10) 0.0231 (6) 0.2959 (2) 0.0451 (19)
H32A 0.2125 0.0606 0.2782 0.068*
H32B 0.0427 0.0623 0.2945 0.068*
H32C 0.1289 −0.0581 0.2886 0.068*
Cl1 0.8741 (3) 0.0986 (3) 0.40005 (6) 0.0749 (8)
Cl2 0.19155 (16) 0.23935 (17) 0.21261 (4) 0.0377 (4)
Cl3 0.5048 (4) 0.6916 (3) 0.53154 (10) 0.1003 (11)
Cl4 0.3193 (4) 0.00695 (16) 0.41503 (6) 0.0640 (7)
O1 0.5416 (8) 0.0109 (5) 0.28270 (19) 0.0639 (18)
O2 0.8737 (5) 0.2326 (5) 0.26670 (12) 0.0361 (11)
O3 0.8599 (4) 0.2414 (4) 0.17650 (11) 0.0299 (9)
O4 0.3243 (5) 0.2411 (5) 0.13414 (12) 0.0419 (11)
O5 0.4639 (4) 0.2336 (4) 0.26919 (11) 0.0297 (9)
O6 0.6320 (8) 0.3498 (7) 0.44516 (19) 0.075 (2)
O7 0.3468 (6) 0.2541 (4) 0.44650 (12) 0.0457 (12)
O8 0.1995 (7) 0.0301 (4) 0.33553 (14) 0.0434 (13)
O9 0.1758 (7) 0.4561 (4) 0.33564 (13) 0.0392 (12)
O10 0.2990 (8) 0.5503 (4) 0.41525 (14) 0.0479 (13)

1 Source of materials

The title compound was synthesized by using our previously reported method 4 , 5 that 2′-hydroxy-griseofulvin (339 mg, 1.0 mmol) reacted with phosphorylchloride (0.56 mL, 5 mmol) in a solution of dioxane (28 mL), and LiCl (212 mg, 5 mmol) was added. Then the mixture was refluxed for about 30 min, cooled to room temperature and sat. aq. sodium carbonate was added until it is slightly basic (pH 7–8). Then extracted with DCM (3 × 20 mL) and the combined organic phases were dried by sodium sulphate anhydrous and concentrated. The residue was purified by column chromatography DCM and the white solid (121 mg) was obtained, yield 45 %. This white solid was recrystallized to obtain colourless crystals from solution (DCM:methanol 5:1) by natural cooling method at room temperature.

2 Experimental details

A suitable crystal was selected and tested on a Xcalibur, Eos, Gemini diffractometer. Using Olex2, 1 the structure was solved with the Shelxt 2 structure solution program using Intrinsic Phasing and refined with the Shelxl 3 refinement package using Least Squares minimisation.

3 Comment

Griseofulvin, a natural product, is the first oral antifungal agent which was used for the treatment of dermatomycoses in humans. 6 Hundreds of griseofulvin analogues have been synthesized 7 and used for bioactivity screening. Recently, we found griseofulvin analogues exhibiting excellent antifungal activities against phytopathogenic fungi. 1 , 8 The title compound (2S,6′R)-4′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzo-furan-2,1′-cyclohexan]-3′-ene-2′,3-dione was synthesized by using 2′-hydroxy-griseofulvin as starting material, and the structure was determined by X-ray single crystal diffraction. It is a key chemical intermediate which was used for synthesis of the 4′-position griseofulvin analogues. 8

The asymmetric unit of the title structure contains two crystallographically independent molecules, and one of these molecules is shown in the figure. In the molecule, the bond length of Cl1–C1 and Cl2–C12 are 1.731(7) Å and 1.729(6) Å respectively. The angle of O2–C7–C8 is 131.5(5)°, the bond lengths and angles of the title compound are similar to the structures of natural product griseofulvin 9 and 2′-chloro-griseofulvin. 2 The plane (C8/C9/C10/C11/C12/C13) of benzene ring and the plane (O5/C4/C7/C8/C13) of furan ring are approximately in the same plane and their dihedral angle is only 3.81°. The plane (O5/C4/C7/C8/C13) of furan ring and the plane (C4/C3/C2) of cyclohexanone present a dihedral angle of about 79.19°. Cyclohexanone ring (C1/C2/C3/C4/C5/C6) has a half-chair conformation. All geometric parameters are in the expected ranges.

Corresponding author: Yu-Bin Bai, College of Chemistry and Chemical Engineering, Yan’an University, Yan’an, Shaanxi 716000, People’s Republic of China, E-mail:

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: National Natural Science Foundation of China (Program No. 22107091), Doctoral Scientific Research Start-Up Fund of Yan’an University (Program No. YDBK2019–03), and College Student Innovation and Entrepreneurship Training Program Project (Program No. D2022087) .

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. 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. Crystallogr. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar

2. Sheldrick, G. M. Shelxtl – Integrated Space-Group and Crystal-Structure Determination. Acta Crystallogr. 2015, A71, 3–8.10.1107/S2053273314026370Search in Google Scholar PubMed PubMed Central

3. Sheldrick, G. M. Crystal Structure Refinement with Shelxl. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar PubMed PubMed Central

4. Bai, Y.-B.; Zhang, M.; Li, D.; Zhao, Y.; Huang, L.-Z.; Gao, J.-M. Synthesis and Antifungal Activity of Derivatives of the Natural Product Griseofulvin Against Phytopathogenic Fungi. J. Agric. Food Chem. 2023, 71, 6236–6248; https://doi.org/10.1021/acs.jafc.2c09037.Search in Google Scholar PubMed

5. Zhang, M.; Bai, Y.-B. The Crystal Structure of (2R,6′R)-2′,7-Dichloro-4,6-Dimethoxy-6′-Methyl-3H-Spiro[Benzofuran-2,1′-Cyclohexan]-2′-Ene-3,4′-Dione, C16H14Cl2O5. Z. Kristallogr. N. Cryst. Struct. 2023, 238, 185–187; https://doi.org/10.1515/ncrs-2022-0538.Search in Google Scholar

6. Oxford, A. E.; Raistrick, H.; Simonart, P. Studies in the Biochemistry of Micro-Organisms: Griseofulvin, C17H17O6Cl, A Metabolic Product of Penicillium griseofulvum Dierckx. Biochem. J. 1939, 33, 240–248; https://doi.org/10.1042/bj0330240.Search in Google Scholar PubMed PubMed Central

7. Dong, N.; Li, X.; Wang, F.; Cheng, J.-P. Asymmetric Michael-Aldol Tandem Reaction of 2-Substituted Benzofuran-3-Ones and Enones: A Facile Synthesis of Griseofulvin Analogues. Org. Lett. 2013, 15, 4896–4899; https://doi.org/10.1021/ol402346c.Search in Google Scholar PubMed

8. Bai, Y.-B.; Gao, Y.-Q.; Nie, X.-D.; Tuong, T.-M.-L.; Li, D.; Gao, J.-M. Antifungal Activity of Griseofulvin Derivatives Against Phytopathogenic Fungi In Vitro and In Vivo and Three-Dimensional Quantitative Structure-Activity Relationship Analysis. J. Agric. Food Chem. 2019, 67, 6125–6132; https://doi.org/10.1021/acs.jafc.9b00606.Search in Google Scholar PubMed

9. Nirmala, K. A.; Sakegowda, D. S.; Duax, W. L. Crystal Structure of Griseofulvin. J. Crystallogr. Spectrosc. Res. 1982, 12, 415–423; https://doi.org/10.1007/bf01161404.Search in Google Scholar
Received: 2024-04-12
Accepted: 2024-05-12
Published Online: 2024-05-31
Published in Print: 2024-08-27

© 2024 the author(s), published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of hexaquazinc(II) poly[hexakis(μ2-4-methylbenzenesulfinato-κ2O:O′) dizinc(II)]
  4. The crystal structure of poly[((2-(4,5-dihydro-1H-pyrazol-4-yl)-1,3-dioxoisoindoline-5-carbonyl)oxy)(1-(dimethylamino)ethoxy)zinc[II]], C16H14ZnN4O5
  5. Crystal structure of bis[(triaqua-4-iodopyridine-2,6-dicarboxylato-κ 3 N,O,O ″)cobalt(II)] trihydrate, C14H22N2O17I2Co2
  6. Crystal structure of bis(methanol-κO)-bis(nitrato-kO)-bis(1-((2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-yl)methyl)-1H-1,2,4-triazole-κN)cadmium(II), C40H42O14N8Cl4Cd
  7. Crystal structure of poly[μ2-dichlorido-(μ2-1-[(2,4-dimethyl-1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2N:N′)cadmium(II)], C11H12CdN6Cl2
  8. The crystal structure of (3aS, 4R, 7S, 7aR)-hexahydro-4, 7-methano-1H-isoindole-1, 3-(2H)-dione, C9H11NO2
  9. The crystal structure of N-(acridin-9-yl)-4-chloro-N-(4-chloro-butanoyl) butanamide, C21H20Cl2N2O2
  10. Crystal structure of 3,3′-dimethoxy-4,4′-oxy-di-benzaldehyde, C16H14O5
  11. The crystal structure of tetrakis(μ 2-2-amino-3,5-dibromobenzoate-κ 2 O:O′)-octakis(n-butyl-κ 1 C)-bis(μ 3-oxo)tetratin(II), C60H92Br8N4O10Sn4
  12. Crystal structure of methyl-1-(naphthalen-1-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H20N2O2
  13. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  14. Crystal structure of 6,6′-((1E,1′E)-((2-phenylpyrimidine-4,6-diyl)bis(hydrazin-2-yl-1-ylidene))bis(methaneylylidene))bis(2-methoxyphenol)monohydrate, C26H26N6O5
  15. Crystal structure of bis(N,N,N-trimethylbutanaminium) tetrathiotungstate(VI), (BuMe3N)2[WS4]
  16. The crystal structure of 2,3,9-triphenyl-9-(2-phenylbenzofuran-3-yl)-9H-9λ 5-benzo[4,5][1,2]oxaphospholo[2,3-b][1,2,5]oxadiphosphole 2-oxide, C40H28O4P2
  17. Crystal structure of 1–methyl-3-propyl-4-nitro-1H-pyrazole-5-carboxylic acid, C8H11N3O4
  18. Crystal structure of N-(benzo[d]thiazol-2-yl)-2-chloroacetamide, C9H7ClN2OS
  19. The crystal structure of N-benzyl-2-chloro-N-(p-tolyl) acetamide, C16H16ClNO
  20. Crystal structure of 3,4-dimethoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O5
  21. Crystal structure of 2,5-bis(2,5-dimethoxybenzyl)-3,6-dimethyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, C26H28N2O6
  22. Crystal structure of poly[(μ3-5-bromoisophthalato-κ4 O,O′ :O″,O‴)-(μ2-1,2-bis(1,2,4-triazole-1-ylmethyl)benzene-κ2 N:N′)cobalt(II)], C20H15BrCoN6O4
  23. The crystal structure of bis(2-(piperidin-1-ium-4-yl)-1Hbenzo[d]imidazol-3-ium) dihydrogen decavanadate, C24H36N6O28V10
  24. Crystal structure of diaqua-bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine3-carboxylato-O,O′)-cobalt(ii)dihydrate, C26H36N4O14Co
  25. Crystal structure of poly[(μ2-5-bromoisophthalato-κ4 O,O ′:O ″,O ‴)-(μ2-1,4-bis(2-methylimidazol-1-ylmethyl)benzene-N:N′)cadmium(II)], C24H21BrCdN4O4
  26. The crystal structure of dimethyl 8-(3-methoxy-2-(methoxycarbonyl)-3-oxoprop-1-en-1-yl)-4-methyl-1-(p-tolyl)-1,3a,4,8b-tetrahydro-3H-furo[3,4-b]indole-3,3-dicarboxylate. C28H29NO9
  27. Crystal structure of (3R)-1-(3,5-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate chloride, C21H23ClN2O4
  28. Synthesis and crystal structure of 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)benzoic acid, C12H13NO5S
  29. The crystal structure of hexaaquamagnesium(II) bis-3-(1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-α]pyridin-1-yl)benzoate, C36H42N4O10Mg
  30. Crystal structure of 4-formyl-2-methoxyphenyl 2-acetoxybenzoate, C17H14O6
  31. Crystal structure of poly[octakis(μ-oxido)-tris(μ-1,1′-[[1,1′-biphenyl]-4,4′-diylbis(methylene)]bis(1H-imidazole))-tetrakis(oxido)-tetra-vanadium-dimanganese(II)dihydrate], C30H29MnN6O7V2
  32. Crystal structure of 4,8a-bis(4-chlorophenyl)-1,5,6-tris(4-fluorobenzyl)-1,4,4a,4b,5,6,8a,8b-octahydrocyclobuta[1,2-b:3,4-c′]dipyridine-3,8-dicarbonitrile, C45H33Cl2F3N4
  33. Crystal structure of benzo[d][1,3]dioxol-5-ylmethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H20O5
  34. Crystal structure of N-benzoyl-N-phenylhydroxylaminato-dicarbonylrhodium(I), [Rh(BNA)CO2]
  35. The crystal structure of N-(2-((2-methoxynaphthalen-1-yl)ethynyl)phenyl)-4-methylbenzenesulfonamide, C26H21NO3S
  36. The crystal structure of methyl ((4-aminobenzyl)sulfonyl)-d-prolinate, C13H18N2O4S
  37. The crystal structure of dichlorido-(N-isopropyl-N-(pyridin-2-ylmethyl)propan-2-amine-κ 2 N, N′)palladium(II), C12H20N2PdCl2
  38. Crystal structure of poly[(μ 2-5-hydroxyisophthalato-κ4 O,O′:O″,O‴)-(μ 2-1,4-bis(2-methylimidazolyl)-1-butene-N:N′)nickel(II)], C20H20NiN4O5
  39. The crystal structure of {hexakis(1-methyl-1H-imidazole-κ 1 N)cobalt(II)}(μ 2-oxido)-hexaoxido-dimolybdenum(VI)— 1-methyl-1H-imidazole (1/2), C32H48CoMo2N16O7
  40. Synthesis, crystal structure and nonlinear optical property of 1-((propan-2-ylideneamino)oxy)propan-2-yl-4-methylbenzenesulfonate, C13H19O4NS
  41. The crystal structure of N,N-(ethane-1,1-diyl)dibenzamide, C16H16N2O2
  42. Crystal structure of 1-(4-bromophenyl)-3-(diphenylphosphoryl)-3-hydroxypropan-1-one, C21H18BrO3P
  43. The crystal structure of fac-tricarbonyl(bis(3,5-dimethyl-4H-pyrazole)-κ1 N)-((nitrato)-κ1 O)-rhenium(I)— 3,5-dimethyl-4H-pyrazole(1/1), C18H23N7O6Re
  44. The crystal structure of 4′-chloro-griseofulvin: (2S,6′R)-4′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-3′-ene-2′,3-dione, C16H14Cl2O5
  45. Crystal structure of tetraethylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  46. Crystal structure of 1-cyclohexyl-4-p-tolyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester, C22H27NO4
  47. The crystal structure of catena-poly(μ2-1,4-bis-(1H-imidazol-1-yl)benzene-copper(I)) dichloridocopper(I), {[CuC12H10N4]+[CuCl2]−} n
  48. The crystal structure of propane-1-aminium-2-carbamate, C4H10N2O2
  49. Crystal structure of 5,6,3′,4′,5′-pentamethoxy-flavone dihydrate, C20H24O9
  50. Crystal structure of (E)-N-(2-bromophenyl)-4-(4-(3,5-dimethoxystyryl)phenoxy)pyrimidin-2-amine, C26H22BrN3O3
  51. Crystal structure of methyl (3R)-1-(2-bromo-4-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride hydrate, C19H19BrClFN2O3
  52. The crystal structure of 1-(2-chlorophenyl)-3-(p-tolyl)urea, C14H13ClN2O
  53. The crystal structure of 1-cyclohexyl-3-(p-tolyl)urea, C14H20N2O
  54. Crystal structure of ((benzyl(hydroxy)-amino)(4-chlorophenyl)methyl)-diphenylphosphine oxide, C26H23ClNO2P
  55. The crystal structure of ethyl 3-(1-methyl-1H-indole-2-carbonyl)-2-phenylquinoline-4-carboxylate, C28H22N2O3
  56. The crystal structure of 1,4-bis(1H-imidazol-3-ium-1-yl)benzene dinitrate, C12H12N4 2+·2(NO3 −)
  57. Crystal structure of tris(hexafluoroacetylacetonato-κ2O,O′) bis(triphenylphosphine oxide-κ1O)samarium(III), C51H33F18O8P2Sm
  58. Crystal structure of 1-(4-(dimethylamino)phenyl)-2,3-bis(diphenylphosphoryl)propan-1-one, C35H33NO3P2
  59. Crystal structure of diaqua[bis(μ 2-pyridine 2,6-dicarboxylato) bismuth(III) potassium(I)], C14H10BiKN2O10
  60. Crystal structure of (R)-N, N ′-dimethyl-[1, 1′-binaphthalene]-2, 2′-diamine, C22H20N2
  61. Crystal structure of 1-phenyl-4-(2-furoyl)-3-furyl-1H-pyrazol-5-ol, C18H12N2O4
  62. Crystal structure of bis(14,34-dimethyl[11,21:23,31-terphenyl]-22-yl)diselane, C40H34Se2
https://doi.org/10.1515/ncrs-2024-0168
Creative Commons
BY 4.0

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of hexaquazinc(II) poly[hexakis(μ2-4-methylbenzenesulfinato-κ2O:O′) dizinc(II)]
  4. The crystal structure of poly[((2-(4,5-dihydro-1H-pyrazol-4-yl)-1,3-dioxoisoindoline-5-carbonyl)oxy)(1-(dimethylamino)ethoxy)zinc[II]], C16H14ZnN4O5
  5. Crystal structure of bis[(triaqua-4-iodopyridine-2,6-dicarboxylato-κ 3 N,O,O ″)cobalt(II)] trihydrate, C14H22N2O17I2Co2
  6. Crystal structure of bis(methanol-κO)-bis(nitrato-kO)-bis(1-((2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-yl)methyl)-1H-1,2,4-triazole-κN)cadmium(II), C40H42O14N8Cl4Cd
  7. Crystal structure of poly[μ2-dichlorido-(μ2-1-[(2,4-dimethyl-1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2N:N′)cadmium(II)], C11H12CdN6Cl2
  8. The crystal structure of (3aS, 4R, 7S, 7aR)-hexahydro-4, 7-methano-1H-isoindole-1, 3-(2H)-dione, C9H11NO2
  9. The crystal structure of N-(acridin-9-yl)-4-chloro-N-(4-chloro-butanoyl) butanamide, C21H20Cl2N2O2
  10. Crystal structure of 3,3′-dimethoxy-4,4′-oxy-di-benzaldehyde, C16H14O5
  11. The crystal structure of tetrakis(μ 2-2-amino-3,5-dibromobenzoate-κ 2 O:O′)-octakis(n-butyl-κ 1 C)-bis(μ 3-oxo)tetratin(II), C60H92Br8N4O10Sn4
  12. Crystal structure of methyl-1-(naphthalen-1-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H20N2O2
  13. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  14. Crystal structure of 6,6′-((1E,1′E)-((2-phenylpyrimidine-4,6-diyl)bis(hydrazin-2-yl-1-ylidene))bis(methaneylylidene))bis(2-methoxyphenol)monohydrate, C26H26N6O5
  15. Crystal structure of bis(N,N,N-trimethylbutanaminium) tetrathiotungstate(VI), (BuMe3N)2[WS4]
  16. The crystal structure of 2,3,9-triphenyl-9-(2-phenylbenzofuran-3-yl)-9H-9λ 5-benzo[4,5][1,2]oxaphospholo[2,3-b][1,2,5]oxadiphosphole 2-oxide, C40H28O4P2
  17. Crystal structure of 1–methyl-3-propyl-4-nitro-1H-pyrazole-5-carboxylic acid, C8H11N3O4
  18. Crystal structure of N-(benzo[d]thiazol-2-yl)-2-chloroacetamide, C9H7ClN2OS
  19. The crystal structure of N-benzyl-2-chloro-N-(p-tolyl) acetamide, C16H16ClNO
  20. Crystal structure of 3,4-dimethoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O5
  21. Crystal structure of 2,5-bis(2,5-dimethoxybenzyl)-3,6-dimethyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, C26H28N2O6
  22. Crystal structure of poly[(μ3-5-bromoisophthalato-κ4 O,O′ :O″,O‴)-(μ2-1,2-bis(1,2,4-triazole-1-ylmethyl)benzene-κ2 N:N′)cobalt(II)], C20H15BrCoN6O4
  23. The crystal structure of bis(2-(piperidin-1-ium-4-yl)-1Hbenzo[d]imidazol-3-ium) dihydrogen decavanadate, C24H36N6O28V10
  24. Crystal structure of diaqua-bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine3-carboxylato-O,O′)-cobalt(ii)dihydrate, C26H36N4O14Co
  25. Crystal structure of poly[(μ2-5-bromoisophthalato-κ4 O,O ′:O ″,O ‴)-(μ2-1,4-bis(2-methylimidazol-1-ylmethyl)benzene-N:N′)cadmium(II)], C24H21BrCdN4O4
  26. The crystal structure of dimethyl 8-(3-methoxy-2-(methoxycarbonyl)-3-oxoprop-1-en-1-yl)-4-methyl-1-(p-tolyl)-1,3a,4,8b-tetrahydro-3H-furo[3,4-b]indole-3,3-dicarboxylate. C28H29NO9
  27. Crystal structure of (3R)-1-(3,5-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate chloride, C21H23ClN2O4
  28. Synthesis and crystal structure of 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)benzoic acid, C12H13NO5S
  29. The crystal structure of hexaaquamagnesium(II) bis-3-(1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-α]pyridin-1-yl)benzoate, C36H42N4O10Mg
  30. Crystal structure of 4-formyl-2-methoxyphenyl 2-acetoxybenzoate, C17H14O6
  31. Crystal structure of poly[octakis(μ-oxido)-tris(μ-1,1′-[[1,1′-biphenyl]-4,4′-diylbis(methylene)]bis(1H-imidazole))-tetrakis(oxido)-tetra-vanadium-dimanganese(II)dihydrate], C30H29MnN6O7V2
  32. Crystal structure of 4,8a-bis(4-chlorophenyl)-1,5,6-tris(4-fluorobenzyl)-1,4,4a,4b,5,6,8a,8b-octahydrocyclobuta[1,2-b:3,4-c′]dipyridine-3,8-dicarbonitrile, C45H33Cl2F3N4
  33. Crystal structure of benzo[d][1,3]dioxol-5-ylmethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H20O5
  34. Crystal structure of N-benzoyl-N-phenylhydroxylaminato-dicarbonylrhodium(I), [Rh(BNA)CO2]
  35. The crystal structure of N-(2-((2-methoxynaphthalen-1-yl)ethynyl)phenyl)-4-methylbenzenesulfonamide, C26H21NO3S
  36. The crystal structure of methyl ((4-aminobenzyl)sulfonyl)-d-prolinate, C13H18N2O4S
  37. The crystal structure of dichlorido-(N-isopropyl-N-(pyridin-2-ylmethyl)propan-2-amine-κ 2 N, N′)palladium(II), C12H20N2PdCl2
  38. Crystal structure of poly[(μ 2-5-hydroxyisophthalato-κ4 O,O′:O″,O‴)-(μ 2-1,4-bis(2-methylimidazolyl)-1-butene-N:N′)nickel(II)], C20H20NiN4O5
  39. The crystal structure of {hexakis(1-methyl-1H-imidazole-κ 1 N)cobalt(II)}(μ 2-oxido)-hexaoxido-dimolybdenum(VI)— 1-methyl-1H-imidazole (1/2), C32H48CoMo2N16O7
  40. Synthesis, crystal structure and nonlinear optical property of 1-((propan-2-ylideneamino)oxy)propan-2-yl-4-methylbenzenesulfonate, C13H19O4NS
  41. The crystal structure of N,N-(ethane-1,1-diyl)dibenzamide, C16H16N2O2
  42. Crystal structure of 1-(4-bromophenyl)-3-(diphenylphosphoryl)-3-hydroxypropan-1-one, C21H18BrO3P
  43. The crystal structure of fac-tricarbonyl(bis(3,5-dimethyl-4H-pyrazole)-κ1 N)-((nitrato)-κ1 O)-rhenium(I)— 3,5-dimethyl-4H-pyrazole(1/1), C18H23N7O6Re
  44. The crystal structure of 4′-chloro-griseofulvin: (2S,6′R)-4′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-3′-ene-2′,3-dione, C16H14Cl2O5
  45. Crystal structure of tetraethylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  46. Crystal structure of 1-cyclohexyl-4-p-tolyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester, C22H27NO4
  47. The crystal structure of catena-poly(μ2-1,4-bis-(1H-imidazol-1-yl)benzene-copper(I)) dichloridocopper(I), {[CuC12H10N4]+[CuCl2]−} n
  48. The crystal structure of propane-1-aminium-2-carbamate, C4H10N2O2
  49. Crystal structure of 5,6,3′,4′,5′-pentamethoxy-flavone dihydrate, C20H24O9
  50. Crystal structure of (E)-N-(2-bromophenyl)-4-(4-(3,5-dimethoxystyryl)phenoxy)pyrimidin-2-amine, C26H22BrN3O3
  51. Crystal structure of methyl (3R)-1-(2-bromo-4-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride hydrate, C19H19BrClFN2O3
  52. The crystal structure of 1-(2-chlorophenyl)-3-(p-tolyl)urea, C14H13ClN2O
  53. The crystal structure of 1-cyclohexyl-3-(p-tolyl)urea, C14H20N2O
  54. Crystal structure of ((benzyl(hydroxy)-amino)(4-chlorophenyl)methyl)-diphenylphosphine oxide, C26H23ClNO2P
  55. The crystal structure of ethyl 3-(1-methyl-1H-indole-2-carbonyl)-2-phenylquinoline-4-carboxylate, C28H22N2O3
  56. The crystal structure of 1,4-bis(1H-imidazol-3-ium-1-yl)benzene dinitrate, C12H12N4 2+·2(NO3 −)
  57. Crystal structure of tris(hexafluoroacetylacetonato-κ2O,O′) bis(triphenylphosphine oxide-κ1O)samarium(III), C51H33F18O8P2Sm
  58. Crystal structure of 1-(4-(dimethylamino)phenyl)-2,3-bis(diphenylphosphoryl)propan-1-one, C35H33NO3P2
  59. Crystal structure of diaqua[bis(μ 2-pyridine 2,6-dicarboxylato) bismuth(III) potassium(I)], C14H10BiKN2O10
  60. Crystal structure of (R)-N, N ′-dimethyl-[1, 1′-binaphthalene]-2, 2′-diamine, C22H20N2
  61. Crystal structure of 1-phenyl-4-(2-furoyl)-3-furyl-1H-pyrazol-5-ol, C18H12N2O4
  62. Crystal structure of bis(14,34-dimethyl[11,21:23,31-terphenyl]-22-yl)diselane, C40H34Se2
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.
© 2025 De Gruyter Brill
Downloaded on 23.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2024-0168/html
Scroll to top button