Home Crystal structure of 6-hydroxy-2,2-dimethyl-4Hbenzo[d][1,3]dioxin-4-one, C10H10O4
Article Open Access

Crystal structure of 6-hydroxy-2,2-dimethyl-4Hbenzo[d][1,3]dioxin-4-one, C10H10O4

  • Wenqiang Tang ORCID logo EMAIL logo , Xiaona Xu , Yanrong Gao , Hongjuan Tong , Zhoujing Zhu and Bin Liu ORCID logo
Published/Copyright: March 23, 2022
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 237 Issue 3

Abstract

C10H10O4, monoclinic, P21/c (no. 14), a = 9.464(6) Å, b = 10.302(7) Å, c = 10.589(7) Å, β = 114.174(11)°, V = 941.8(10) Å3, Z = 4, R gt (F) = 0.0453, wRref(F2) = 0.1394, T = 173 K.

CCDC no.: 1888828

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: Colorless block
Size: 0.25 × 0.15 × 0.12 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.11 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 25.5°, >99%
N(hkl)measured, N(hkl)unique, Rint: 6747, 1745, 0.077
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 1430
N(param)refined: 130
Programs: Bruker [1], Olex2 [2], SHELX [3, 4]
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.31562 (17) 0.52265 (13) 0.58259 (14) 0.0282 (4)
C2 0.30498 (19) 0.44095 (14) 0.68240 (15) 0.0351 (4)
H2 0.328459 0.472000 0.773267 0.042*
C3 0.25983 (19) 0.31403 (15) 0.64773 (15) 0.0367 (4)
H3 0.254006 0.257258 0.716136 0.044*
C4 0.22242 (18) 0.26707 (14) 0.51400 (15) 0.0321 (4)
C5 0.23322 (18) 0.34836 (13) 0.41527 (15) 0.0301 (4)
H5 0.207936 0.317576 0.324001 0.036*
C6 0.28166 (16) 0.47653 (13) 0.45022 (13) 0.0273 (4)
C7 0.30899 (16) 0.56230 (13) 0.35136 (14) 0.0277 (4)
C8 0.14348 (18) 0.76360 (15) 0.45187 (15) 0.0372 (4)
H8A 0.087107 0.681107 0.427801 0.056*
H8B 0.111140 0.818796 0.369422 0.056*
H8C 0.120682 0.807590 0.523447 0.056*
C9 0.31532 (17) 0.73786 (13) 0.50570 (14) 0.0286 (4)
C10 0.4155 (2) 0.85627 (14) 0.55551 (17) 0.0379 (4)
H10A 0.400708 0.894287 0.634049 0.057*
H10B 0.386848 0.919938 0.480353 0.057*
H10C 0.524441 0.831828 0.584623 0.057*
O1 0.36664 (12) 0.64789 (9) 0.61812 (9) 0.0318 (3)
O2 0.34939 (12) 0.68546 (9) 0.39268 (9) 0.0317 (3)
O3 0.30478 (12) 0.52798 (9) 0.24067 (10) 0.0360 (3)
O4 0.17591 (15) 0.14061 (10) 0.48902 (12) 0.0437 (4)
H4 0.178817 0.116393 0.414378 0.066*

Source of material

The thionyl chloride (7.5 mL, 103.82 mmol) was slowly added to a solution of 2,5-dihydroxybenzoic acid (8.0 g, 51.91 mmol) in acetone (30 mL) at 0 °C with stirring under a N2 atmosphere. The 4-dimethylaminopyridine (8.0 g, 51.91 mmol) was added and the solution was stirred at 0 °C for 1 h. The mixture was kept at room temperature for 16 h. After the reaction completion (monitored by thin-layer chromatography), the mixture was diluted with saturated NaHCO3 solution and extracted with ethyl acetate. The organic layer was dried and concentrated under reduced pressure. The title compound was separated by silica-gel column chromatography using ethyl acetate/petroleum ether (10%). The target product was obtained as a white solid. The crystals were obtained by slow evaporation of mixed solution of petroleum ether and ethyl acetate (10:1, v/v) at room temperature after one week.

Experimental details

All H atoms were included using a riding model, with C–H = 0.95–0.98 Å with their Uiso = 1.2Ueq and with O–H = 0.84 Å and their Uiso = 1.5Ueq.

Comment

Heterocycles and their derivatives play significant roles in natural products and synthetic chemistry as intermediates [5, 6]. For instance, benzodioxane is an oxygen isomeric heterocyclic compound with various applications in medicine, agriculture, and synthetic chemistry [7, 8]. Among the isomers of benzodioxane, 1,3-benzodioxane and its derivatives can serve as intermediates in the chemical synthesis for pharmaceutical, natural product, and pesticide chemistry research [9], [10], [11]. Furthermore, they are potential synthetic intermediates in multistep organic synthesis. Among various 1,3-benzodioxane derivatives, 4H-benzo[d][1,3]dioxin-4-one and its derivatives have been identified in nucleoside transport inhibitors, biologically active molecules such as isomerase I inhibitors, anti-plasma parasite, and cytotoxic drugs, insecticides, crop protection agents, and fungicides [12], [13], [14]. Up to date, a significant number of 4H-benzo[d][1,3]dioxin-4-one derivatives have been reported [15], [16], [17], [18], [19], [20], [21], [22], [23], [24]. This paper reports the synthesis and crystal structure of a novel 4H-benzo[d][1,3]dioxin-4-one derivative compound.

The asymmetric unit contains one molecule of the title compound, where two methyl groups and one hydroxyl group replace the hydrogen atom on the 4H-benzo[d][1,3]dioxin-4-one configuration (see the Figure). The bond lengths of C9–C8, C9–C10, and C4–O4 are 1.510(3) Å, 1.502(3) Å, and 1.366(2) Å, respectively. The C–C bond lengths of the benzo moiety are in the range of 1.376(3)–1.398(3) Å, and the C–C–C angles are in the range of 118.96(15)–121.37(16)°, indicating the substitution of functional groups did not significantly change the structure. The dihedral angle of the almost flat moiety: C1···C7, O1, and O2 and the plane (C9, O1, and O2) is 43.86°. And the dihedral angle of the plane A (C9, O1, and O2) and the plane B (C8, C9, and C10) is 90.63°. The only intermolecular O4–H4···O3 hydrogen bond is observed. The O4–H4 and O3–H4 bond lengths are 0.8399(15) Å and 1.9385(16) Å. The molecule’s structure is similar to the configurations of the compounds reported in the references [15, 16, 22, 24].

Corresponding author: Wenqiang Tang, Collaborative Innovation Center of Green Manufacturing Technology for Traditional Chinese Medicine in Shaanxi Province, School of Pharmacy, Shaanxi Institute of International Trade & Commerce, Xi’an, China, E-mail:

Funding source: Natural Science Foundation of Shaanxi Province http://dx.doi.org/10.13039/501100007128

Award Identifier / Grant number: 2021JQ-883

Funding source: Collaborative Innovation Center of Green Manufacturing Technology for Traditional Chinese Medicine in Shaanxi Province http://dx.doi.org/10.13039/501100009103

Award Identifier / Grant number: 2019XT-1-02

Funding source: Shaanxi Institute of International Trade & Commerce http://dx.doi.org/10.13039/501100009103

Award Identifier / Grant number: SSY18TD01

Funding source: Key Laboratory of Molecular Imaging and Drug Synthesis of Xianyang City http://dx.doi.org/10.13039/501100011710

Award Identifier / Grant number: 2021QXNL-PT-0008

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

  2. Research funding: This work was financially supported by the Natural Science Foundation of Shaanxi Province (2021JQ-883), Key breeding program by the Collaborative Innovation Center of Green Manufacturing Technology for Traditional Chinese Medicine in Shaanxi Province (2019XT-1-02), and Effective Substances of Traditional Chinese Medicine Innovative Team in Shaanxi Institute of International Trade & Commerce (SSY18TD01), and Key Laboratory of Molecular Imaging and Drug Synthesis of Xianyang City (2021QXNL-PT-0008).

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

References

1. Bruker. SMART APEX-II CCD. Bruker AXS Inc.: Madison, WI, USA, 2006.Search in Google Scholar

2. 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

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

4. Sheldrick, G. M. SHELXTL – integrated space-group and crystal-structure determination. Acta Crystallogr. 2015, A71, 3–8; https://doi.org/10.1107/s2053273314026370.Search in Google Scholar

5. Lefebvre, C., Fortier, L., Hoffmann, N. Photochemical rearrangements in heterocyclic chemistry. Eur. J. Org Chem. 2020, 2020, 1393–1404; https://doi.org/10.1002/ejoc.201901190.Search in Google Scholar

6. Algul, O., Ersan, R. H., Alagoz, M. A., Duran, N., Burmaoglu, S. An efficient synthesis of novel di-heterocyclic benzazole derivatives and evaluation of their antiproliferative activities. J. Biomol. Struct. Dyn. 2021, 39, 6926–6938; https://doi.org/10.1080/07391102.2020.1803966.Search in Google Scholar

7. Bolchi, C., Bavo, F., Appiani, R., Roda, G., Pallavicini, M. 1,4-Benzodioxane, an evergreen, versatile scaffold in medicinal chemistry: a review of its recent applications in drug design. Eur. J. Med. Chem. 2020, 200, 112419; https://doi.org/10.1016/j.ejmech.2020.112419.Search in Google Scholar

8. Shehzad, M. T., Khan, A., Islam, M., Hameed, A., Khiat, M., Halim, S. A., Anwar, M. U., Shah, S. R., Hussain, J., Csuk, R., Khan, S., Al-Harrasi, A., Shafiq, Z. Synthesis and urease inhibitory activity of 1,4-benzodioxane-based thiosemicarbazones: biochemical and computational approach. J. Mol. Struct. 2020, 1209, 127922; https://doi.org/10.1016/j.molstruc.2020.127922.Search in Google Scholar

9. Shah, S. U. A., Ashraf, N., Soomro, Z. H., Shah, M. R., Kabir, N., Simjee, S. U. The anti-arthritic and anti-oxidative effect of NBD (6-nitro-1,3-benzodioxane) in adjuvant-induced arthritis (AIA) in rats. Inflamm. Res. 2012, 61, 875–887; https://doi.org/10.1007/s00011-012-0480-4.Search in Google Scholar

10. Clososki, G. C., Rohbogner, C. J., Knochel, P. Direct magnesiation of polyfunctionalized arenes and heteroarenes using (tmp)2Mg…2LiCl. Angew. Chem. Int. Ed. 2007, 46, 7681–7684; https://doi.org/10.1002/anie.200701487.Search in Google Scholar

11. Bhaskaran, R. P., Nayak, K. H., Babu, B. P. Synthesis of functionalized benzo [1, 3] dioxin-4-ones from salicylic acid and acetylenic esters and their direct amidation. RSC Adv. 2021, 11, 24570–24574; https://doi.org/10.1039/d1ra05032j.Search in Google Scholar

12. Tasdelen, M. A., Yagci, Y. Benzodioxinone photochemistry in macromolecular science: progress, challenges, and opportunities. ACS Macro Lett. 2017, 6, 1392–1397; https://doi.org/10.1021/acsmacrolett.7b00788.Search in Google Scholar

13. Cooper, T. S., Atrash, B., Sheldrake, P., Workman, P., McDonald, E. Synthesis of resorcinylic macrocycles related to radicicol via ring-closing metathesis. Tetrahedron Lett. 2006, 47, 2241–2243; https://doi.org/10.1016/j.tetlet.2006.01.117.Search in Google Scholar

14. Cookson, R., Barrett, T. N., Barrett, A. G. β-Keto-dioxinones and β, δ-diketo-dioxinones in biomimetic resorcylate total synthesis. Acc. Chem. Res. 2015, 48, 628–642; https://doi.org/10.1021/ar5004169.Search in Google Scholar

15. Patel, C., Mies, T., White, A. J., Parsons, P. J., Barrett, A. G. Biomimetic syntheses of Amorfrutin C and C-5 substituted Amorfrutin analogues. Eur. J. Org Chem. 2021, 2021, 1258–1265; https://doi.org/10.1002/ejoc.202001487.Search in Google Scholar

16. Muthusamy, S., Malarvizhi, M., Suresh, E. Catalyst-free synthesis of 3,1-benzoxathiin-4-ones/1,3-benzodioxin-4-ones. Org. Biomol. Chem. 2021, 19, 1508–1513; https://doi.org/10.1039/d0ob02543g.Search in Google Scholar

17. Jorgensen, J.-E., Hansen, A. B. Structure and conformation of 2-methyl-2-(2-naphthyloxy)-4H-1,3-benzodioxin-4-one. Acta Crystallogr. 1982, B38, 991–993; https://doi.org/10.1107/s0567740882004713.Search in Google Scholar

18. Jensen, K. Structure of an aspirin derivative: 2-(2-methoxybenzyloxy)-2-methyl-4H-1,3-benzodioxin-4-one. Acta Crystallogr. 1990, C46, 2416–2419; https://doi.org/10.1107/s0108270190003729.Search in Google Scholar

19. Jana, N., Das, D., Nanda, S. Asymmetric total synthesis of 5′-epi-cochliomycin C. Tetrahedron 2013, 69, 2900–2908; https://doi.org/10.1016/j.tet.2013.02.033.Search in Google Scholar

20. Irving, A., Irving, H. M. N. H. 6,8-Dinitro-1,3-benzodioxin-4-one. Acta Crystallogr. 1988, C44, 1228–1230; https://doi.org/10.1107/s0108270188002434.Search in Google Scholar

21. Irving, A., Irving, H. M. N. H. Structure and conformation of 6-nitro-2-trichloromethyl-1,3-benzdioxin-4-one: X-ray crystallographic determination. J. Crystallogr. Spectrosc. Res. 1986, 16, 607–616; https://doi.org/10.1007/bf01161048.Search in Google Scholar

22. Elliott, D. C., Ma, T.-K., Selmani, A., Cookson, R., Parsons, P. J., Barrett, A. G. M. Sequential ketene generation from dioxane-4,6-dione-keto-dioxinones for the synthesis of terpenoid resorcylates. Org. Lett. 2016, 18, 1800–1803; https://doi.org/10.1021/acs.orglett.6b00533.Search in Google Scholar

23. Chen, X., Wang, H., Doitomi, K., Ooi, C. Y., Zheng, P., Liu, W., Guo, H., Yang, S., Song, B.-A., Hirao, H., Chi, Y. R. A reaction mode of carbene-catalysed aryl aldehyde activation and induced phenol OH functionalization. Nat. Commun. 2017, 8, 15598; https://doi.org/10.1038/ncomms15598.Search in Google Scholar

24. Tisdale, E. J., Vong, B. G., Li, H., Kim, S. H., Chowdhury, C., Theodorakis, E. A. Total synthesis of seco-lateriflorone. Tetrahedron 2003, 59, 6873–6887; https://doi.org/10.1016/s0040-4020(03)00862-7.Search in Google Scholar
Received: 2022-01-26
Accepted: 2022-03-14
Published Online: 2022-03-23
Published in Print: 2022-06-27

© 2022 Wenqiang Tang et al., 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 (E)-(4-imidazol-1-yl-phenyl)-(2-methoxy-benzylidene)-amine monohydrate, C17H17N3O2
  4. Crystal structure of 6-methyl-3-(pyrrolidine-1-carbonyl)-2H-chromen-2-one, C15H15N1O3
  5. Crystal structure of 4-methyl-4-nitropentanoic acid, C6H11NO4
  6. The crystal structure of (E)-3-(furan-2-yl)acrylonitrile, C7H5NO
  7. Crystal structure of 3-(difluoromethyl)-1-methyl-N-(4,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methanoacridin-9-yl)-1H-pyrazole-4-carboxamide monohydrate, C23H26F2N4O3
  8. Crystal structure of 2-(4-bromobenzyloxy)-6-chloropyridine, C12H9BrClNO
  9. Crystal structure of N-(4-bromo-2,6-dichloro-phenyl)pyrazin-2-amine, C10H6BrCl2N3
  10. Crystal structure of (E)-1-(2–nitrophenyl)-3-phenylprop-2-en-1-one, C15H11NO3
  11. The crystal structure of (E)-3-chloro-2-(2-(4-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3
  12. Crystal structure of (E)-amino(2-(thiazol-2-ylmethylene)hydrazineyl)methaniminium nitrate, C10H16N12O6S2
  13. Crystal structure of 9-methoxy-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C15H18N4O
  14. The crystal structure bis(dimethylsulfoxide-κ1O)-dipyridine-κ1 N-bis(m2-(Z)-3-methyl-2-oxido-N-((Z)-oxido(phenyl)methylene)benzohydrazonato-κ5)trinickel(II) - dimethylsulfoxide (1/2), C48H56N6Ni3O10S4
  15. Crystal structure of bis(bis(triphenylphosphine)iminium) tetradecacarbonyltetratelluridopentaferrate(2-), (PPN)2[Fe5Te4(CO)14]
  16. Crystal structure of 4-Hydroxy-3-(naphthalen-2-ylthio)pent-3-en-2-one, C15H14O2S
  17. The crystal structure of [(1,10-phenanthroline-κ2 N,N)-bis(6-phenylpyridine-2-carboxylate-κ2 N,O)nickel(II)] monohydrate, C36H26N4O5Ni
  18. Crystal structure of 3,3′-(pyridine-2,6-diylbis(methylene))bis(1-propyl-1H-imidazol-3-ium) ditetrafluoroborate, C19H27B2F8N5
  19. The crystal structure of (E)-1-(4-aminophenyl)-3-(p-tolyl)prop-2-en-1-one, C16H15NO
  20. The crystal structure of poly[(μ2-terephthalato-κ4O,O′: O″,O‴)-(μ4-terephthalato-κ4O:O′:O″:O‴)-{μ4-(1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ4O:O′:O″,O‴)}dicadmium(II)] – water – acetronitrile (1/2/2), C38H36N14O10Cd2
  21. The crystal structure of diaqua-bis(6-phenylpyridine-2-carboxylato-κ2 N,O)cobalt(II)–water–N,N-dimethylformamide(1/2/1), C27H31N3O9Co
  22. The co-crystal structure of 4-hydroxy-3-methoxybenzoic acid – 4,4′-bipyridine, C8H8O4·C10H8N2
  23. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)cobalt(II)], C32H22Br2CoN4O4
  24. Crystal structure of (E)-5-propyl-4-((pyridin-2-ylmethylene)amino)-2,4-dihydro-3H-1,2,4-triazole-3-thione – methanol (1/1), C11H13N5S
  25. The crystal structure of (Z)-4-bromo-6-(((1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)amino)methylene)cyclohexa-2,4-dien-1-one monohydrate, C11H16BrNO5
  26. Crystal structure of bis(tetrapropylammonium) nonaselenidotetrastannate(IV), (Pr4N)2[Sn4Se9]
  27. Crystal structure of 2,6-di-tert-butyl-4-(4-chlorobenzylidene)cyclohexa-2,5-dien-1-one, C21H25ClO
  28. Crystal structure of (2,2′-((naphthalen-1-ylmethyl)azanediyl)diacetato-κ3 N,O,O′)-(1,10-phenanthroline-κ2 N,N′)-copper(II) trihydrate, CuC27H27N3O7
  29. The crystal structure of tetrakis(6-phenylpyridine-2-carboxylato-κ2N,O)-bis(1H-pyrazol-3-ylamine-κ2 N:N)dicobalt(II) dihydrate, C27H23N5O5Co
  30. The crystal structure of bis((E)-2-((tert-butylimino)methyl)-4-chlorophenolato-κ2N,O)zinc(II), C22H26Cl2N2O2Zn
  31. The crystal structure of poly[diaqua-(μ3-5-nitrobenzene-1,2,3-tricarboxylato-κ3O:O′:O′)-(μ2-4,4′-dipyridylamine-κ2N:N′)copper(II)], C38H30Cu3N8O20
  32. The crystal structure of (E)-1-ferrocenyl-3-(naphthalen-1-yl)prop-2-en-1-one, C23H18FeO
  33. The crystal structure of (E)-1-ferrocenyl-3-(4-isopropylphenyl)prop-2-en-1-one, C22H22FeO
  34. Crystal structure of 6-hydroxy-2,2-dimethyl-4Hbenzo[d][1,3]dioxin-4-one, C10H10O4
  35. The crystal structure of (2E,4E)-1-ferrocenyl-5-phenylpenta-2,4-dien-1-one, C21H18FeO
  36. Crystal structure of alaninato-κ2N,O-bis(hydroxylamido-κ2N,O)-oxido-vanadium(V), C3H10N3O5V
  37. Crystal structure of catena-poly[aqua-bis[μ2-6-(1H-imidazol-1-yl)nicotinato-κ2 N,O]copper(II)], C18H14N6O5Cu
  38. Crystal structure of diethyl 4,6-diphenyl-1,9-di-p-tolylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,5(2H)-dicarboxylate, C42H42N2O4
  39. The crystal structure of cobalt cadmium bis(hydrogenphosphate) bis(phosphate(V)) tetrahydrate, H10O20P4Co3.14Cd1.86
  40. Crystal structure of dimethyl 1,4,6,9-tetraphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,7(2H)-dicarboxylate, C38H34N2O4
  41. Crystal structure of (Z)-4-(furan-2-yl((4-iodophenyl)amino)methylene)-5-methyl-2(p-tolyl)-2,4-dihydro-3H-pyrazol-3-one, C21H16I N3O2
  42. Crystal structure of (E)-1-(4-(3,5-dimethoxystyryl)phenyl)-7-ethylheptanedioate, C25H30O6
  43. Crystal structure of 6-bromo-2-(4-chlorophenyl)chroman-4-one (6-bromo-4′-chloroflavanone), C15H10BrClO2
  44. The crystal structure of 2-(benzhydryloxy)-3-nitropyridine, C18H14N2O3
  45. The crystal structure of 1,3(4,1)-dipyridin-1-iuma-2(1,8)-diethynylanthracena-5(1,3)-benzenacyclohexaphane-11,31-diium bis(hexafluoridophosphate), C36H24F12N2P2
  46. Crystal structure of 3,6-di-tert-butyl-1-iodo-9-methyl-8-(pyren-1-ylethynyl)-9H-carbazole, C39H34IN
  47. The cocrystal 2-(dimethylammonio)-5-nitrobenzoate – 2-(dimethylamino)-5-nitrobenzoic acid, C9H10N2O4
  48. Crystal structure of 5-nitroquinazolin-4(3H)-one, C8H5N3O3
https://doi.org/10.1515/ncrs-2022-0054
Creative Commons
BY 4.0

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of (E)-(4-imidazol-1-yl-phenyl)-(2-methoxy-benzylidene)-amine monohydrate, C17H17N3O2
  4. Crystal structure of 6-methyl-3-(pyrrolidine-1-carbonyl)-2H-chromen-2-one, C15H15N1O3
  5. Crystal structure of 4-methyl-4-nitropentanoic acid, C6H11NO4
  6. The crystal structure of (E)-3-(furan-2-yl)acrylonitrile, C7H5NO
  7. Crystal structure of 3-(difluoromethyl)-1-methyl-N-(4,11,11-trimethyl-1,2,3,4-tetrahydro-1,4-methanoacridin-9-yl)-1H-pyrazole-4-carboxamide monohydrate, C23H26F2N4O3
  8. Crystal structure of 2-(4-bromobenzyloxy)-6-chloropyridine, C12H9BrClNO
  9. Crystal structure of N-(4-bromo-2,6-dichloro-phenyl)pyrazin-2-amine, C10H6BrCl2N3
  10. Crystal structure of (E)-1-(2–nitrophenyl)-3-phenylprop-2-en-1-one, C15H11NO3
  11. The crystal structure of (E)-3-chloro-2-(2-(4-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3
  12. Crystal structure of (E)-amino(2-(thiazol-2-ylmethylene)hydrazineyl)methaniminium nitrate, C10H16N12O6S2
  13. Crystal structure of 9-methoxy-2,3,4,4a,5,6-hexahydro-1H-pyrido [1′,2′:1,6]pyrazino[2,3-b]quinoxaline, C15H18N4O
  14. The crystal structure bis(dimethylsulfoxide-κ1O)-dipyridine-κ1 N-bis(m2-(Z)-3-methyl-2-oxido-N-((Z)-oxido(phenyl)methylene)benzohydrazonato-κ5)trinickel(II) - dimethylsulfoxide (1/2), C48H56N6Ni3O10S4
  15. Crystal structure of bis(bis(triphenylphosphine)iminium) tetradecacarbonyltetratelluridopentaferrate(2-), (PPN)2[Fe5Te4(CO)14]
  16. Crystal structure of 4-Hydroxy-3-(naphthalen-2-ylthio)pent-3-en-2-one, C15H14O2S
  17. The crystal structure of [(1,10-phenanthroline-κ2 N,N)-bis(6-phenylpyridine-2-carboxylate-κ2 N,O)nickel(II)] monohydrate, C36H26N4O5Ni
  18. Crystal structure of 3,3′-(pyridine-2,6-diylbis(methylene))bis(1-propyl-1H-imidazol-3-ium) ditetrafluoroborate, C19H27B2F8N5
  19. The crystal structure of (E)-1-(4-aminophenyl)-3-(p-tolyl)prop-2-en-1-one, C16H15NO
  20. The crystal structure of poly[(μ2-terephthalato-κ4O,O′: O″,O‴)-(μ4-terephthalato-κ4O:O′:O″:O‴)-{μ4-(1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ4O:O′:O″,O‴)}dicadmium(II)] – water – acetronitrile (1/2/2), C38H36N14O10Cd2
  21. The crystal structure of diaqua-bis(6-phenylpyridine-2-carboxylato-κ2 N,O)cobalt(II)–water–N,N-dimethylformamide(1/2/1), C27H31N3O9Co
  22. The co-crystal structure of 4-hydroxy-3-methoxybenzoic acid – 4,4′-bipyridine, C8H8O4·C10H8N2
  23. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)cobalt(II)], C32H22Br2CoN4O4
  24. Crystal structure of (E)-5-propyl-4-((pyridin-2-ylmethylene)amino)-2,4-dihydro-3H-1,2,4-triazole-3-thione – methanol (1/1), C11H13N5S
  25. The crystal structure of (Z)-4-bromo-6-(((1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)amino)methylene)cyclohexa-2,4-dien-1-one monohydrate, C11H16BrNO5
  26. Crystal structure of bis(tetrapropylammonium) nonaselenidotetrastannate(IV), (Pr4N)2[Sn4Se9]
  27. Crystal structure of 2,6-di-tert-butyl-4-(4-chlorobenzylidene)cyclohexa-2,5-dien-1-one, C21H25ClO
  28. Crystal structure of (2,2′-((naphthalen-1-ylmethyl)azanediyl)diacetato-κ3 N,O,O′)-(1,10-phenanthroline-κ2 N,N′)-copper(II) trihydrate, CuC27H27N3O7
  29. The crystal structure of tetrakis(6-phenylpyridine-2-carboxylato-κ2N,O)-bis(1H-pyrazol-3-ylamine-κ2 N:N)dicobalt(II) dihydrate, C27H23N5O5Co
  30. The crystal structure of bis((E)-2-((tert-butylimino)methyl)-4-chlorophenolato-κ2N,O)zinc(II), C22H26Cl2N2O2Zn
  31. The crystal structure of poly[diaqua-(μ3-5-nitrobenzene-1,2,3-tricarboxylato-κ3O:O′:O′)-(μ2-4,4′-dipyridylamine-κ2N:N′)copper(II)], C38H30Cu3N8O20
  32. The crystal structure of (E)-1-ferrocenyl-3-(naphthalen-1-yl)prop-2-en-1-one, C23H18FeO
  33. The crystal structure of (E)-1-ferrocenyl-3-(4-isopropylphenyl)prop-2-en-1-one, C22H22FeO
  34. Crystal structure of 6-hydroxy-2,2-dimethyl-4Hbenzo[d][1,3]dioxin-4-one, C10H10O4
  35. The crystal structure of (2E,4E)-1-ferrocenyl-5-phenylpenta-2,4-dien-1-one, C21H18FeO
  36. Crystal structure of alaninato-κ2N,O-bis(hydroxylamido-κ2N,O)-oxido-vanadium(V), C3H10N3O5V
  37. Crystal structure of catena-poly[aqua-bis[μ2-6-(1H-imidazol-1-yl)nicotinato-κ2 N,O]copper(II)], C18H14N6O5Cu
  38. Crystal structure of diethyl 4,6-diphenyl-1,9-di-p-tolylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,5(2H)-dicarboxylate, C42H42N2O4
  39. The crystal structure of cobalt cadmium bis(hydrogenphosphate) bis(phosphate(V)) tetrahydrate, H10O20P4Co3.14Cd1.86
  40. Crystal structure of dimethyl 1,4,6,9-tetraphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta[b]pyridine-3,7(2H)-dicarboxylate, C38H34N2O4
  41. Crystal structure of (Z)-4-(furan-2-yl((4-iodophenyl)amino)methylene)-5-methyl-2(p-tolyl)-2,4-dihydro-3H-pyrazol-3-one, C21H16I N3O2
  42. Crystal structure of (E)-1-(4-(3,5-dimethoxystyryl)phenyl)-7-ethylheptanedioate, C25H30O6
  43. Crystal structure of 6-bromo-2-(4-chlorophenyl)chroman-4-one (6-bromo-4′-chloroflavanone), C15H10BrClO2
  44. The crystal structure of 2-(benzhydryloxy)-3-nitropyridine, C18H14N2O3
  45. The crystal structure of 1,3(4,1)-dipyridin-1-iuma-2(1,8)-diethynylanthracena-5(1,3)-benzenacyclohexaphane-11,31-diium bis(hexafluoridophosphate), C36H24F12N2P2
  46. Crystal structure of 3,6-di-tert-butyl-1-iodo-9-methyl-8-(pyren-1-ylethynyl)-9H-carbazole, C39H34IN
  47. The cocrystal 2-(dimethylammonio)-5-nitrobenzoate – 2-(dimethylamino)-5-nitrobenzoic acid, C9H10N2O4
  48. Crystal structure of 5-nitroquinazolin-4(3H)-one, C8H5N3O3
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 5.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2022-0054/html
Scroll to top button