Home The crystal structure of 2-anilino-1,4-naphthoquinone, C10H11NO2
Article Open Access

The crystal structure of 2-anilino-1,4-naphthoquinone, C10H11NO2

  • Mohammed A. Elmakki ORCID logo EMAIL logo , Thato N. Taoana , Frederick J. F. Jacobs and Johan A. Venter
Published/Copyright: September 4, 2023
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 238 Issue 6

Abstract

C10H11NO2, monoclinic, P21/n (no. 14), a = 3.7617(3) Å, b = 12.9267(10) Å, c = 23.4609(17) Å, β = 92.337(3)°, V = 1139.87(15) Å3, Z = 4, R gt (F) = 0.0413, wR ref (F 2) = 0.1071, T = 100 K.

CCDC no.: 2289189

The molecular structure is shown in the figure. 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: Red needle
Size: 0.43 × 0.08 × 0.04 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.10 mm−1
Diffractometer, scan mode: Bruker D8 Venture 5K Kappa Photon III
θ max, completeness: 28.3°, >99 %
N(hkl)measured , N(hkl)unique, R int: 19,336, 2811, 0.049
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2294
N(param)refined: 176
Programs: SHELX [1], Bruker [2], Olex2 [3], Diamond [4]
Table 2:

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

Atom x y z U iso*/U eq
O1 0.0055 (3) 0.58217 (7) 0.54884 (4) 0.0222 (2)
O2 0.7062 (3) 0.53632 (7) 0.75009 (4) 0.0244 (2)
N1 0.2742 (3) 0.39814 (8) 0.57225 (5) 0.0181 (2)
C1 0.5409 (4) 0.08329 (10) 0.58117 (6) 0.0246 (3)
H1A 0.601030 0.011946 0.582759 0.029*
C2 0.4078 (4) 0.13178 (10) 0.62849 (6) 0.0238 (3)
H2 0.376798 0.093575 0.662524 0.029*
C3 0.3196 (4) 0.23610 (10) 0.62628 (5) 0.0202 (3)
H3 0.225596 0.269034 0.658583 0.024*
C4 0.3695 (3) 0.29224 (10) 0.57662 (5) 0.0176 (3)
C5 0.3273 (3) 0.47199 (9) 0.61246 (5) 0.0165 (2)
C6 0.5037 (3) 0.46219 (9) 0.66401 (5) 0.0181 (3)
H6 0.601033 0.396728 0.674412 0.022*
C7 0.5485 (3) 0.54705 (9) 0.70343 (5) 0.0174 (3)
C8 0.4056 (3) 0.65055 (9) 0.68593 (5) 0.0161 (2)
C9 0.4586 (3) 0.73502 (10) 0.72194 (5) 0.0188 (3)
H9 0.579777 0.726369 0.757950 0.023*
C10 0.3345 (3) 0.83196 (10) 0.70533 (6) 0.0211 (3)
H10 0.370949 0.889558 0.730028 0.025*
C11 0.1571 (3) 0.84512 (10) 0.65265 (6) 0.0211 (3)
H11 0.071867 0.911634 0.641588 0.025*
C12 0.1041 (3) 0.76178 (10) 0.61629 (6) 0.0188 (3)
H12 −0.016143 0.770941 0.580245 0.023*
C13 0.2288 (3) 0.66391 (9) 0.63293 (5) 0.0163 (2)
C14 0.1717 (3) 0.57481 (9) 0.59454 (5) 0.0165 (3)
C15 0.5014 (3) 0.24358 (10) 0.52911 (5) 0.0195 (3)
H15 0.533653 0.281620 0.495064 0.023*
C16 0.5859 (4) 0.13895 (10) 0.53164 (6) 0.0235 (3)
H16 0.675241 0.105472 0.499134 0.028*
H1 0.182 (5) 0.4211 (14) 0.5380 (8) 0.032 (5)*

1 Source of materials

The 2-anilino-1,4-naphthoquinone was purchased from Sigma Aldrich and then dissolved in 3 mL acetone. The solution was kept to room temperature for crystallization. Red cuboid crystals were obtained.

2 Experimental details

The aromatic H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with fixed C–H distances for aromatic C–H of 0.93 Å (C–H) [U iso(H) = 1.2U eq]. The N1–H1 hydrogen was placed according to the Fourier electron difference density map. The graphics were obtained using the DIAMOND [4] program with 50 % probability ellipsoids. The highest peak is located 0.68 Å from C6 and the deepest hole is situated 0.61 Å from C14 respectively.

3 Comment

It is known that cancer is one of the diseases that have a great impact on our daily lives, and much scientific research is being conducted in order to limit and get rid of this incurable disease.

Epidermal growth factor receptor (EGFR) has been recognized as a very important aim for anticancer drug development. The 2-anilino-1,4-naphthoquinone and its derivatives have been shown to be related to be potential for their anticancer and EGFR inhibitor [5]. One of the most important naphthalene derivatives is naphthoquinone, with two carbonyl groups it is a privileged scaffold found in many classes of naturally occurring bioactive compounds and it has been used and its derivatives for cancer treatment [6, 7]. Different molecular mechanisms with regard to anticancer activities of the naphthoquinone-based compounds have been described [8], [9], [10]. In our laboratory, we have many results on the possibility of coordinating such compounds with the platinum group metals to increase the possibility to have an impact on cancer [11, 12].

There is one molecule in the asymmetric unit of the title structure. In the title structure, the O1–C14, O2–C7, N1–C4 and N1–C5 bond lengths were determined as 1.2219(17), 1.2312(17), 1.4176(17) and 1.3504(17) respectively. The C5–N1–C4, C3–C4–N1, C15–C4–N1, N1–C5–C6, N1–C5–C14, O2–C7–C6, O2–C7–C8, O1–C14–C5 and O1–C14–C13 bond angles were determined as 127.04(12), 121.45(12), 118.47(12), 127.41(12), 112.59(12), 121.66(12), 120.04(12) and 119.53(12) respectively. All parameters are in the expected ranges [13–15].

Corresponding author: Mohammed A. Elmakki, Department of Chemistry, University of the Free State, 9301 Bloemfontein, South Africa; and Department of Chemistry Omdurman, Islamic University, 14415 Omdurman, Sudan, 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: The authors acknowledge funding under the Swiss-South Africa joint research program (SSAJRP) from the SANRF (A. Roodt: UID: 107802) as well as from the Competitive Program for Rated Researchers of the SANRF (A. Roodt: UID: 111698), from the South African Department of Science Innovation (DSI) and the Department of Science and Technology (DST) respectively, “Department of Science and Innovation, Republic of South Africa” and “Department of Science and Technology, Republic of South Africa”.

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

References

1. Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. 2008, A64, 112–122; https://doi.org/10.1107/s0108767307043930.Search in Google Scholar PubMed

2. Bruker. SAINT-Plus (Version 7.12) and SADABS (Version 2004/1); Bruker AXS Inc.: Madison, WI, USA, 2004.Search in Google Scholar

3. 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

4. Brandenburg, K. DIAMOND. Visual Crystal Structure Information System. 3.0c; Crystal Impact: Bonn, Germany, 2005.Search in Google Scholar

5. Mahalapbutr, P., Leechaisit, R., Thongnum, A., Todsaporn, D., Prachayasittikul, V., Rungrotmongkol, T., Prachayasittikul, S., Ruchirawat, S., Prachayasittikul, V., Pingaew, R. Discovery of anilino-1,4-naphthoquinones as potent EGFR tyrosine kinase inhibitors: synthesis, biological evaluation, and comprehensive molecular modeling. ACS Omega 2022, 7, 17881–17893; https://doi.org/10.1021/acsomega.2c01188.Search in Google Scholar PubMed PubMed Central

6. El-Najjar, N., Gali-Muhtasib, H., Ketola, R. A., Vuorela, P., Urtti, A., Vuorela, H. The chemical and biological activities of quinones: overview and implications in analytical detection. Photochem. Rev. 2011, 10, 353–370; https://doi.org/10.1007/s11101-011-9209-1.Search in Google Scholar

7. Sunassee, S. N., Davies-Coleman, M. T. Cytotoxic and antioxidant marine prenylated quinones and hydroquinones. Nat. Prod. Rep. 2012, 29, 513–535; https://doi.org/10.1039/c2np00086e.Search in Google Scholar PubMed

8. Pereyra, C. E., Dantas, R. F., Ferreira, S. B., Gomes, L. P., Silva, F. P.Jr. The diverse mechanisms and anticancer potential of naphthoquinones. Cancer Cell Int. 2019, 19, 207–226; https://doi.org/10.1186/s12935-019-0925-8.Search in Google Scholar PubMed PubMed Central

9. Salustiano, E. J. S., Netto, C. D., Fernandes, R. F., da Silva, A. J. M., Bacelar, T. S., Castro, C. P., Buarque, C. D., Maia, R. C., Rumjanek, V. M., Costa, P. R. R. Comparison of the cytotoxic effect of lapachol, alpha-lapachone and pentacyclic 1,4-naphthoquinones on human leukemic cells. Invest. New Drugs 2010, 28, 139–144; https://doi.org/10.1007/s10637-009-9231-y.Search in Google Scholar PubMed

10. Wellington, K. W. Understanding cancer and the anticancer activities of naphthoquinones? A review. RSC Adv. 2015, 5, 20309–20338; https://doi.org/10.1039/c4ra13547d.Search in Google Scholar

11. Elmakki, M. A. E., Alexander, O. T., Venter, G. J. S., Venter, J. A., Roodt, A. Structural study and iodomethane oxidative addition mechanistic investigation on model rhodium(I) carbonylation catalysts activated by indole-2-/indoline-2-carboxylate bidentate ligands. Inorganics 2022, 10, 1–24.10.3390/inorganics10120251Search in Google Scholar

12. Manicum, A. L., Visser, H. G., Engelbrecht, I., Roodt, A. Crystal structure of fac-(acetylacetonato-κ2O,O′)tricarbonyl (cyclohexyldiphenylphosphine-κP)rhenium(I), C26H28O5Pre. Z. Kristallogr. N. Cryst. Struct. 2015, 230, 150–152; https://doi.org/10.1515/ncrs-2014-9013.Search in Google Scholar

13. Jha, R. K., Batabyal, M., Kumar, S. Blue light irradiated metal-oxidant-and base-free cross-dehydrogenative coupling of C(sp2)–H and N–H bonds: amination of naphthoquinones with amines. J. Org. Chem. 2023, 88, 7401–7424; https://doi.org/10.1021/acs.joc.3c00666.Search in Google Scholar PubMed

14. Singh, M. W., Karmakar, A., Barooah, N., Baruah, J. B. Variations in product in reactions of naphthoquinone with primary amines. Beilstein J. Org. Chem. 2007, 3, 10; https://doi.org/10.1186/1860-5397-3-10.Search in Google Scholar PubMed PubMed Central

15. Bayen, S., Barooah, N., Sarma, R. J., Sen, T. K., Karmakar, A., Baruah, J. B. Synthesis, structure and electrochemical properties of 2,5-bis(alkyl/arylamino)1,4-benzoquinones and 2-arylamino-1,4-naphthoquinones. Dyes Pigments 2007, 75, 770–775; https://doi.org/10.1016/j.dyepig.2006.07.033.Search in Google Scholar
Received: 2023-07-19
Accepted: 2023-08-17
Published Online: 2023-09-04
Published in Print: 2023-12-15

© 2023 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. Crystal structure of bis(dimethylammonium) poly[(μ4-1,1′-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato))-κ6O1, N2:O2:O3:O1′,N2′]nickel (II)], C22H26N6NiO8
  4. Hydrothermal synthesis and crystal structure of catena-poly[diaqua-bis(μ2-4-((pyridin-4-ylmethyl)amino)benzoato-κ2N:O)cobalt(II)] – 4,4′-bipyridine – water (1/2/2)
  5. Crystal structure of (2S,3S,4S,5S, Z)-2,3,5,6-tetrakis(benzyloxy)-4-hydroxyhexanal oxime, C34H37NO6
  6. The crystal structure of hexakis(3-thiophenecarboxylato-κ2O,O″)-bis(1,10-phenanthroline-κ2N,N′) trimanganese(II), C54H34N4O12S6Mn3
  7. Crystal structure of catena-poly[(μ2-1,4-di(pyridin-4-yl)benzene-κ2N:N′)-(4-bromobenzoate-κ2O:O′)-(μ-2-bromobenzoate-κ2O,O′)nickel(II)] – water (2/1), C30H21Br2N2NiO4.5
  8. The crystal structure of poly[(μ3-1,3-phenylenedioxydiacetate-κ5O,O,O′,O″,O‴)-bis(4′-(4-(1H-imidazol-1-yl)phenyl)-4,2′:6′,4″-terpyridine-kN) cadmium(II)], C58H42CdN10O6
  9. The crystal structure of 5-chloro-6′-methyl-3-(4-(methylsulfonyl)phenyl)-[2,3′-bipyridin]-1′-ium 4-methylbenzenesulfonate
  10. Crystal structure of poly[(μ-benzoato)-(μ-cis-4–hydroxy-D-proline)lithium], C12H14LiNO5
  11. The crystal structure of catena-poly[aqua-(4-iodopyridine-2,6-dicarboxylato-κ3N,O,O′)-copper(II)] monohydrate, C7H6NO6ICu
  12. The crystal structure of catena-[diaqua-(4-acetylphenoxyacetato-κ2O,O)-bis(4-acetylphenoxyacetato-κ3O,O:O)-dihydrate-lanthanum(III)]–4,4′-bipyridine (2/1), C35H35NO14La
  13. The crystal structure of catena-poly[(4-iodopyridine-2,6-dicarboxylato-κ4 O,N,O′,O′′)(4-imidazol-1-yl-pyridine-κN)copper(II)], C15H9N4O4ICu
  14. Crystal structure of polybis(μ 4-3,5-dicarboxylatopyrazol-1-yl)-bis(N,N-dimethylformamide)tri-copper(II)–acetonitrile (1/2), C20H22Cu3N8O10
  15. Crystal structure of poly[(μ2-5-hydroxy-isophthalato-κ4O,O′:O″,O‴)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N′)cadmium(II)], C21H24CdN4O5
  16. The crystal structure of poly[bis(μ2-1,4-bi(1-imidazolyl)benzene-κ2N:N′)bis(μ2-4,4′-methylenebis(3-hydroxy-2-naphthoate)-κ2O:O′)cobalt(II)], C35H24CoN4O6
  17. The crystal structure of a cobalt-vanadium-oxido hydrate
  18. The crystal structure of catena-poly[(μ 2-2H-1,2,3-triazole-4,5-dicarboxylato-κ 2 O, O′)-(μ 2-1,3-bis((1H-imidazol-1-yl)methyl)benzene-κ 2 N,N′) zinc(II)], C18H15N7O4Zn
  19. Crystal structure of poly[diaqua-(bis(m2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′-manganese] dichloride, C28H32MnN8O2Cl2
  20. The crystal structure of 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino [3,2-a]isoquinolin-7-ium (E)-3-(4-nitrophenyl)acrylate pentahydrate, C29H34N2O13
  21. Crystal structure of poly[(μ6-ammoniotris(methylene))tris(hydrogen phosphonato)cadmium(II)], C3H10CdNO9P3
  22. Crystal structure of Zn2[(1,1′-(hexane-1,6-diyl)bis(3-(pyridin-3-yl)urea))·(H2O)2·(DMF)2·(SO4)2], C24H50N8O18S2Zn2
  23. The crystal structure of 2-anilino-1,4-naphthoquinone, C10H11NO2
  24. Crystal structure of (E)-2-(2-(4-(diethylamino)styryl)-1-ethyl-1,4-dihydroquinolin-4-yl) malononitrile, C26H26N4
  25. Crystal structure of ethyl 2-((2,6-dichloro-4-(cyanomethyl)phenyl) amino)benzoate, C17H14Cl2N2O2
  26. Synthesis and crystal structure of 2-(3-oxo-3-phenylpropyl)isoindoline-1,3-dione, C17H13NO3
  27. The crystal structure of bis(acetonitrile-κ1N)tetrakis(μ2-2,6-difluorobenzoato-κ2O:O′)rhodium(II) (Rh–Rh), C32H18F8O8N2Rh2
  28. The crystal structure of a new polymorph of 6-hydroxy-2-naphthoic acid, C11H8O3
  29. The crystal structure of [(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)-2,2′-bipyridine-κ2N-copper(II)] tetrahydrate, C22H23N3O9Cu
  30. The crystal structure of ethyl 4-hydroxy-2-(4-methoxyphenyl)-5-oxo-1-(2-oxo-2H-chromen-6-yl)-2,5-dihydro-1H-pyrrole-3-carboxylate, C23H19NO7
  31. Crystal structure of 7-hydroxy-3,4-dihydronaphthalen-1(2H)-one, C10H10O2
  32. Crystal structure of bis(tetrapropylammonium) dodecacarbonyltetratelluridotetraferrate(2-), (Pr4N)2[Fe4Te4(CO)12]
  33. The crystal structure of poly[bis(μ2−3−aminopyridine−4−carboxylato−κ2N:O)Zinc(II)], [Zn(C6H5N2O2)2] n
  34. The crystal structure of methyl 5-nitro-2-(tosyloxy)benzoate, C15H13NO7S
  35. The crystal structure of 18-crown-6 ― tetraaqua-dichlorido-di-μ2-chloridodicopper(II) (2/1), C12H32O10Cu2Cl4
  36. Crystal structure of 6,6a,7,8,9,10-hexahydro-5H-pyrazino [2,3-e]pyrido[1,2-a]pyrazine, C10H14N4
  37. Crystal structure of catena-poly-{diaqua-bis[μ-(((4-chlorophenyl)sulfonyl)glycinato-κO)](μ2-4, 4′-bipyridine-κ2N:N′)cobalt(II)} dihydrate, C26H30Cl2CoN4O12S2
  38. Crystal structure of bis{N′-[1,3-diphenylprop-2-en-1-ylidene]-N-phenylcarbamohydrazonothioato}zinc(II), C44H36N6S2Zn
  39. Crystal structure of tetraaqua-bis(((4-chlorophenyl)sulfonyl)glycinato-κO)cobalt(II) dihydrate, C16H26Cl2CoN2O14S2
  40. Crystal structure of 2-(5-phenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol, C24H19N3O
  41. Crystal structure of 2-((2-fluoro-4-(trifluoromethyl)phenyl)(hydroxy)methyl)-7-methoxy-3,4-dihydronaphthalen-1((2H))-one, C19H16F4O3
  42. Crystal structure of 2-amino-4-(2-fluoro-3-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  43. Crystal structure of (2-phenylimino methylquinoline-κ 2 N,N′)-bis(1–phenylpyrazole-κ 2 C,N)-iridium(III) hexafluorophosphate, C34H26F6IrN6P
  44. Crystal structure of (3-hydroxy-4-methoxyphenyl)(pyrrolidin-1-yl)methanone, C12H15NO3
  45. The crystal structure of bis(trimethylsulfoxonium) catena-poly[µ2-hexabromido-indium(III)sodium(I)] C6H18O2S2NaInBr6
  46. Crystal structure of N-cyclopropyl-3-hydroxy-4-methoxybenzamide, C11H13NO3
  47. The crystal structure of (bis(benzimidazol-2-yl-methyl)amine-κ3N,N′,N″ )-(dihydrogen L-malate-κ2O,O ′)copper(II) perchlorate dihydrate, CuC20H24ClN5O12
  48. Crystal structure of (1E,1′E)-4,4′-(9,9-diethyl-9H-fluorene-2,7-diyl)dibenzaldehyde dioxime, C31H28N2O2
  49. Crystal structure of diethyl 1,9-bis(4-fluorophenyl)-4,6-diphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta [b]pyridine-3,7(2H)-dicarboxylate, C40H36F2N2O4
  50. Crystal structure of bis(benzene-1 carboxylato-O 3,5-carboxyl-κ1O)-[(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) ─ benzene-1,3,5-tricarboxylic acid ─ water (1/2/4), C52H66N4NiO28
  51. Crystal structure of 1,4-dibromo-2,5-bis(2-methoxyethoxy)benzene-1,4-diol, C12H16Br2O4
  52. Crystal structure of dicarbonyl[N,N′-(1,2-dimethyl-1,2-ethanediylidene)bis[2,6-bis(1-methylethyl)benzenamine]-N,N′]nickel(0), C30H40N2NiO2
  53. Crystal structure of 1,4-dibromo-2,5-bis(prop-2-yn-1-yloxy)benzene, C12H8Br2O2
  54. Crystal structure of O-(3-(benzo[d]thiazol-2-yl)naphthalen-2-yl) O-phenyl carbonothioate, C24H15NO2S2
  55. The crystal structure of (E)-4-fluoro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
  56. Crystal structure of (E)-1-(benzo[d]thiazol-2-yl)-N-(4,5-dihydropyren-2-yl)methanimine, C24H16N2S
  57. Crystal structure of 3-((4-bromophenyl)thio)-1H-indole, C14H10BrNS
  58. Synthesis and crystal structure of 1-((7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carboxylate monohydrate, C22H22N2O9
  59. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α]phenanthren-3-one O-(methacryloyl) oxime, C50H74N2O4
  60. Crystal structure of the hydrogen storage active phase La12Mg46LiMn
  61. The crystal structure of the salt: 4-((1,3-dioxoisoindolin-2-yl)carbamoyl)pyridine-1-ium 2-carboxybenzoate, C14H10N3O3·C8H5O4
  62. Crystal structure of (2-(2-pyridine)-benzimidazole-κ2 N,N′)-bis(1-phenylpyrazole-κ2 C,N)iridium(III) hexafluorophosphate, C30H22F6IrN7P
  63. Crystal structure of dichlorido-bis[2-(2,4-difluorophenyl)pyridine-κ1N]platinum(II), C22H14Cl2F4N2Pt
  64. Crystal structure of (5R,8R,9R,10R,12R,13R,14R, 17S,17Z)-2-((3-fluoropyridin-4-yl)methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one, C36H52FNO3
https://doi.org/10.1515/ncrs-2023-0338
Creative Commons
BY 4.0

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of bis(dimethylammonium) poly[(μ4-1,1′-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato))-κ6O1, N2:O2:O3:O1′,N2′]nickel (II)], C22H26N6NiO8
  4. Hydrothermal synthesis and crystal structure of catena-poly[diaqua-bis(μ2-4-((pyridin-4-ylmethyl)amino)benzoato-κ2N:O)cobalt(II)] – 4,4′-bipyridine – water (1/2/2)
  5. Crystal structure of (2S,3S,4S,5S, Z)-2,3,5,6-tetrakis(benzyloxy)-4-hydroxyhexanal oxime, C34H37NO6
  6. The crystal structure of hexakis(3-thiophenecarboxylato-κ2O,O″)-bis(1,10-phenanthroline-κ2N,N′) trimanganese(II), C54H34N4O12S6Mn3
  7. Crystal structure of catena-poly[(μ2-1,4-di(pyridin-4-yl)benzene-κ2N:N′)-(4-bromobenzoate-κ2O:O′)-(μ-2-bromobenzoate-κ2O,O′)nickel(II)] – water (2/1), C30H21Br2N2NiO4.5
  8. The crystal structure of poly[(μ3-1,3-phenylenedioxydiacetate-κ5O,O,O′,O″,O‴)-bis(4′-(4-(1H-imidazol-1-yl)phenyl)-4,2′:6′,4″-terpyridine-kN) cadmium(II)], C58H42CdN10O6
  9. The crystal structure of 5-chloro-6′-methyl-3-(4-(methylsulfonyl)phenyl)-[2,3′-bipyridin]-1′-ium 4-methylbenzenesulfonate
  10. Crystal structure of poly[(μ-benzoato)-(μ-cis-4–hydroxy-D-proline)lithium], C12H14LiNO5
  11. The crystal structure of catena-poly[aqua-(4-iodopyridine-2,6-dicarboxylato-κ3N,O,O′)-copper(II)] monohydrate, C7H6NO6ICu
  12. The crystal structure of catena-[diaqua-(4-acetylphenoxyacetato-κ2O,O)-bis(4-acetylphenoxyacetato-κ3O,O:O)-dihydrate-lanthanum(III)]–4,4′-bipyridine (2/1), C35H35NO14La
  13. The crystal structure of catena-poly[(4-iodopyridine-2,6-dicarboxylato-κ4 O,N,O′,O′′)(4-imidazol-1-yl-pyridine-κN)copper(II)], C15H9N4O4ICu
  14. Crystal structure of polybis(μ 4-3,5-dicarboxylatopyrazol-1-yl)-bis(N,N-dimethylformamide)tri-copper(II)–acetonitrile (1/2), C20H22Cu3N8O10
  15. Crystal structure of poly[(μ2-5-hydroxy-isophthalato-κ4O,O′:O″,O‴)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N′)cadmium(II)], C21H24CdN4O5
  16. The crystal structure of poly[bis(μ2-1,4-bi(1-imidazolyl)benzene-κ2N:N′)bis(μ2-4,4′-methylenebis(3-hydroxy-2-naphthoate)-κ2O:O′)cobalt(II)], C35H24CoN4O6
  17. The crystal structure of a cobalt-vanadium-oxido hydrate
  18. The crystal structure of catena-poly[(μ 2-2H-1,2,3-triazole-4,5-dicarboxylato-κ 2 O, O′)-(μ 2-1,3-bis((1H-imidazol-1-yl)methyl)benzene-κ 2 N,N′) zinc(II)], C18H15N7O4Zn
  19. Crystal structure of poly[diaqua-(bis(m2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′-manganese] dichloride, C28H32MnN8O2Cl2
  20. The crystal structure of 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino [3,2-a]isoquinolin-7-ium (E)-3-(4-nitrophenyl)acrylate pentahydrate, C29H34N2O13
  21. Crystal structure of poly[(μ6-ammoniotris(methylene))tris(hydrogen phosphonato)cadmium(II)], C3H10CdNO9P3
  22. Crystal structure of Zn2[(1,1′-(hexane-1,6-diyl)bis(3-(pyridin-3-yl)urea))·(H2O)2·(DMF)2·(SO4)2], C24H50N8O18S2Zn2
  23. The crystal structure of 2-anilino-1,4-naphthoquinone, C10H11NO2
  24. Crystal structure of (E)-2-(2-(4-(diethylamino)styryl)-1-ethyl-1,4-dihydroquinolin-4-yl) malononitrile, C26H26N4
  25. Crystal structure of ethyl 2-((2,6-dichloro-4-(cyanomethyl)phenyl) amino)benzoate, C17H14Cl2N2O2
  26. Synthesis and crystal structure of 2-(3-oxo-3-phenylpropyl)isoindoline-1,3-dione, C17H13NO3
  27. The crystal structure of bis(acetonitrile-κ1N)tetrakis(μ2-2,6-difluorobenzoato-κ2O:O′)rhodium(II) (Rh–Rh), C32H18F8O8N2Rh2
  28. The crystal structure of a new polymorph of 6-hydroxy-2-naphthoic acid, C11H8O3
  29. The crystal structure of [(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)-2,2′-bipyridine-κ2N-copper(II)] tetrahydrate, C22H23N3O9Cu
  30. The crystal structure of ethyl 4-hydroxy-2-(4-methoxyphenyl)-5-oxo-1-(2-oxo-2H-chromen-6-yl)-2,5-dihydro-1H-pyrrole-3-carboxylate, C23H19NO7
  31. Crystal structure of 7-hydroxy-3,4-dihydronaphthalen-1(2H)-one, C10H10O2
  32. Crystal structure of bis(tetrapropylammonium) dodecacarbonyltetratelluridotetraferrate(2-), (Pr4N)2[Fe4Te4(CO)12]
  33. The crystal structure of poly[bis(μ2−3−aminopyridine−4−carboxylato−κ2N:O)Zinc(II)], [Zn(C6H5N2O2)2] n
  34. The crystal structure of methyl 5-nitro-2-(tosyloxy)benzoate, C15H13NO7S
  35. The crystal structure of 18-crown-6 ― tetraaqua-dichlorido-di-μ2-chloridodicopper(II) (2/1), C12H32O10Cu2Cl4
  36. Crystal structure of 6,6a,7,8,9,10-hexahydro-5H-pyrazino [2,3-e]pyrido[1,2-a]pyrazine, C10H14N4
  37. Crystal structure of catena-poly-{diaqua-bis[μ-(((4-chlorophenyl)sulfonyl)glycinato-κO)](μ2-4, 4′-bipyridine-κ2N:N′)cobalt(II)} dihydrate, C26H30Cl2CoN4O12S2
  38. Crystal structure of bis{N′-[1,3-diphenylprop-2-en-1-ylidene]-N-phenylcarbamohydrazonothioato}zinc(II), C44H36N6S2Zn
  39. Crystal structure of tetraaqua-bis(((4-chlorophenyl)sulfonyl)glycinato-κO)cobalt(II) dihydrate, C16H26Cl2CoN2O14S2
  40. Crystal structure of 2-(5-phenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol, C24H19N3O
  41. Crystal structure of 2-((2-fluoro-4-(trifluoromethyl)phenyl)(hydroxy)methyl)-7-methoxy-3,4-dihydronaphthalen-1((2H))-one, C19H16F4O3
  42. Crystal structure of 2-amino-4-(2-fluoro-3-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  43. Crystal structure of (2-phenylimino methylquinoline-κ 2 N,N′)-bis(1–phenylpyrazole-κ 2 C,N)-iridium(III) hexafluorophosphate, C34H26F6IrN6P
  44. Crystal structure of (3-hydroxy-4-methoxyphenyl)(pyrrolidin-1-yl)methanone, C12H15NO3
  45. The crystal structure of bis(trimethylsulfoxonium) catena-poly[µ2-hexabromido-indium(III)sodium(I)] C6H18O2S2NaInBr6
  46. Crystal structure of N-cyclopropyl-3-hydroxy-4-methoxybenzamide, C11H13NO3
  47. The crystal structure of (bis(benzimidazol-2-yl-methyl)amine-κ3N,N′,N″ )-(dihydrogen L-malate-κ2O,O ′)copper(II) perchlorate dihydrate, CuC20H24ClN5O12
  48. Crystal structure of (1E,1′E)-4,4′-(9,9-diethyl-9H-fluorene-2,7-diyl)dibenzaldehyde dioxime, C31H28N2O2
  49. Crystal structure of diethyl 1,9-bis(4-fluorophenyl)-4,6-diphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta [b]pyridine-3,7(2H)-dicarboxylate, C40H36F2N2O4
  50. Crystal structure of bis(benzene-1 carboxylato-O 3,5-carboxyl-κ1O)-[(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) ─ benzene-1,3,5-tricarboxylic acid ─ water (1/2/4), C52H66N4NiO28
  51. Crystal structure of 1,4-dibromo-2,5-bis(2-methoxyethoxy)benzene-1,4-diol, C12H16Br2O4
  52. Crystal structure of dicarbonyl[N,N′-(1,2-dimethyl-1,2-ethanediylidene)bis[2,6-bis(1-methylethyl)benzenamine]-N,N′]nickel(0), C30H40N2NiO2
  53. Crystal structure of 1,4-dibromo-2,5-bis(prop-2-yn-1-yloxy)benzene, C12H8Br2O2
  54. Crystal structure of O-(3-(benzo[d]thiazol-2-yl)naphthalen-2-yl) O-phenyl carbonothioate, C24H15NO2S2
  55. The crystal structure of (E)-4-fluoro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
  56. Crystal structure of (E)-1-(benzo[d]thiazol-2-yl)-N-(4,5-dihydropyren-2-yl)methanimine, C24H16N2S
  57. Crystal structure of 3-((4-bromophenyl)thio)-1H-indole, C14H10BrNS
  58. Synthesis and crystal structure of 1-((7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carboxylate monohydrate, C22H22N2O9
  59. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α]phenanthren-3-one O-(methacryloyl) oxime, C50H74N2O4
  60. Crystal structure of the hydrogen storage active phase La12Mg46LiMn
  61. The crystal structure of the salt: 4-((1,3-dioxoisoindolin-2-yl)carbamoyl)pyridine-1-ium 2-carboxybenzoate, C14H10N3O3·C8H5O4
  62. Crystal structure of (2-(2-pyridine)-benzimidazole-κ2 N,N′)-bis(1-phenylpyrazole-κ2 C,N)iridium(III) hexafluorophosphate, C30H22F6IrN7P
  63. Crystal structure of dichlorido-bis[2-(2,4-difluorophenyl)pyridine-κ1N]platinum(II), C22H14Cl2F4N2Pt
  64. Crystal structure of (5R,8R,9R,10R,12R,13R,14R, 17S,17Z)-2-((3-fluoropyridin-4-yl)methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one, C36H52FNO3
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 13.10.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2023-0338/html?srsltid=AfmBOopN1SNTZpY53PaTCg6kVCWTx61I0_xUomfABN4SrPQwSHAKwAQn
Scroll to top button