Startseite Crystal structure of 3-nitrophenol-2,1,3-benzoselenadiazole (1/1), C12H9N3O3Se
Artikel Open Access

Crystal structure of 3-nitrophenol-2,1,3-benzoselenadiazole (1/1), C12H9N3O3Se

  • Jian-Ge Wang EMAIL logo
Veröffentlicht/Copyright: 2. Oktober 2024

Abstract

C12H9N3O3Se, monoclinic, P21/c (no. 14), a = 3.9106(3) Å, b = 23.5453(14) Å, c = 13.4611(8) Å, β =  92.697 ( 6 ) ° , V = 1238.07(14) Å3, Z = 4, R gt (F) = 0.0432, ωR ref (F 2) = 0.0786, T = 290 K.

CCDC no.: 2251363

The asymmetric unit of the title crystal 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 × 0.24 × 0.21 mm
Wavelength: Mo radiation (0.71073 Å)
μ: 3.04 mm−1
Diffractometer, scan mode: SuperNova, ω
θ max, completeness: 28.4°, >99%
N(hkl)measured , N(hkl)unique, R int: 9024, 2709, 0.033
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2124
N(param)refined: 173
Programs: CrysAlisPro [1], SHELX [2], [3], Olex2 [4]
Table 2:

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

Atom x y z U iso*/U eq
Se1 0.44256 (9) 0.55392 (2) 0.89226 (2) 0.04105 (13)
N1 0.2846 (7) 0.55800 (11) 0.7653 (2) 0.0421 (7)
N2 0.3121 (7) 0.48169(11) 0.90576 (19) 0.0395 (7)
C1 0.1481 (8) 0.50795 (13) 0.7420 (2) 0.0345 (7)
C2 0.1642 (8) 0.46575 (13) 0.8197 (2) 0.0326 (7)
C3 0.0239 (9) 0.41080 (14) 0.7998 (3) 0.0444 (8)
H3 0.0307 0.3831 0.8491 0.053*
C4 −0.1188 (9) 0.39948 (15) 0.7089 (3) 0.0477 (9)
H4 −0.2091 0.3636 0.6959 0.057*
C5 −0.1344 (9) 0.44102 (15) 0.6326 (3) 0.0479 (9)
H5 −0.2365 0.4318 0.5709 0.057*
C6 −0.0055 (9) 0.49346 (15) 0.6471 (3) 0.0453 (9)
H6 −0.0162 0.5200 0.5958 0.054*
O1 0.5223 (7) 0.61149 (10) 0.59512 (18) 0.0574 (7)
H1 0.4605 0.6031 0.6506 0.086*
O2 0.8942 (8) 0.73963 (12) 0.3359 (2) 0.0691 (8)
O3 0.7645 (8) 0.82264 (11) 0.3821 (2) 0.0724 (9)
N3 0.7669 (8) 0.77224 (14) 0.3933 (2) 0.0489 (8)
C7 0.4997 (8) 0.66826 (13) 0.5824 (2) 0.0353 (7)
C8 0.6323( 8) 0.69083 (13) 0.4970 (2) 0.0362 (8)
H8 0.7305 0.6674 0.4505 0.043*
C9 0.6148 (8) 0.74837 (13) 0.4830 (2) 0.0338 (7)
C10 0.4733 (9) 0.78504 (15) 0.5490 (3) 0.0455 (9)
H10 0.4659 0.8240 0.5376 0.055*
C11 0.3425 (9) 0.76131 (16) 0.6331 (3) 0.0490 (9)
H11 0.2439 0.7848 0.6793 0.059*
C12 0.3546 (8) 0.70396 (15) 0.6501 (2) 0.0416 (8)
H12 0.2651 0.6890 0.7073 0.050*

1 Source of materials

All reagents and solvents were used as obtained without further purification. The methanol solution (10 mL) of 3-nitrophenol (0.10 mmol, 0.0139 g) was slowly added to another methanol solution (10 mL) of 2,1,3-benzoselenadiazole (0.1 mmol, 0.0183 g). The mixture was stirred for 2 h at room temperature. The solution was filtered, and the filtrate was kept at the room temperature. After 1 week colorless crystals of the title compound were obtained.

2 Experimental details

The hydrogen atoms were assigned with common isotropic displacement factors U iso(H) = 1.2 times U eq (C, aromatic ring), U iso(H) = 1.5 times U eq(OH). The final refinement by using geometrical restraints, with C–H = 0.93 Å (aromatic ring), O–H = 0.82 Å (OH).

3 Comment

With their unique structures and interesting physicochemical properties, supramolecular compounds attract much attention [5], [6], [7]. In general, the different components are linked together by one or more intermolecular interactions such as hydrogen bonds, forming high ordered supramolecular cocrystal structures [8], [9], [10]. As known, the nitrogen atoms of polyaza heteroaromatic compounds can serve as weak base to accept protons from carboxylic acid to form acid-base conjugate pair incorporating charge transfer interactions, which enable the potential characteristic of the construction of cocrystals. In this paper, we report the reaction product of the nitrogen heterocyclic compound 2,1,3-benzoselenadiazole together with 3-nitrophenol.

The asymmetric unit of the title structure contains one 2,1,3-benzoselenadiazole and one 3-nitrophenol. The dimers of two 2,1,3-benzoselenadiazole molecules are formed by a pair of N–Se⋯N chalcogen bonds. And the adjacent dimers are connected by O–H⋯N hydrogen bonds and N–Se⋯O chalcogen bonds to form a two dimensional network. Bond lengths and angles are all in the expected ranges [11].


Corresponding author: Jian-Ge Wang, College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang, Henan 471022, P.R. 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: None declared.

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

References

1. Agilent Technologies. CrysAlisPro; Agilent Technologies: Santa Clara, CA, USA, 2017.Suche in Google Scholar

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

3. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Suche in Google Scholar

4. 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.Suche in Google Scholar

5. Liu, R., Gao, Y. J., Jin, W. J. Color-tunable phosphorescence of 1,10-phenanthrolines by 4,7-methyl/-diphenyl/-dichloro substituents in cocrystals assembled via bifurcated C–I⋯N halogen bonds using 1,4-diiodotetrafluorobenzene as a bonding donor. Acta Crystallogr. 2017, B73, 247–254.10.1107/S205252061700292XSuche in Google Scholar PubMed

6. Kapadia, P. P., Ditzler, L. R., Baltrusaitis, J., Swenson, D. C., Tivanski, A. V., Pigge, C. Semiconducting organic complexes prepared from tetraphenylethylene tetracarboxylic acid and bis(pyridine)s via charge-assisted hydrogen bonding. J. Am. Chem. Soc. 2011, 133, 8490–8493; https://doi.org/10.1021/ja203001z.Suche in Google Scholar PubMed

7. Thomas, S., Satheeshkumar, K., Mugesh, G., Guru Row, T. N. Unusually short chalcogen bonds involving organoselenium: insights into the Se–N bond cleavage mechanism of the antioxidant ebselen and analogues. Chem. Eur J. 2015, 21, 1–9; https://doi.org/10.1002/chem.201405998.Suche in Google Scholar PubMed

8. Wang, H., Jin, W. J. Cocrystals assembled by 1,4-diiodotetrafluorobenzene and phenothiazine based on C–I⋯Π/N/S halogen bond and other assisting interactions. Acta Crystallogr. 2017, B73, 210–216.10.1107/S2052520617002918Suche in Google Scholar PubMed

9. Colquhoun, H. M., Williams, D. J., Zhu, Z. Macrocyclic aromatic ether-imide-sulfones: versatile supramolecular receptors with extreme thermochemical and oxidative stability. J. Am. Chem. Soc. 2002, 124, 13346–13347; https://doi.org/10.1021/ja027851m.Suche in Google Scholar PubMed

10. Eichstaedt, K., Wasilewska, A., Wicher, B., Gdaniec, M., Polonski, T. Supramolecular synthesis based on a combination of Se⋯N secondary bonding interactions with hydrogen and halogen bonds. Cryst. Growth Des. 2016, 16, 1282–1293; https://doi.org/10.1021/acs.cgd.5b01356.Suche in Google Scholar

11. Hubner, T., Gieren, A. The crystal structures of two polyiodide salts of organic cations. Acta Crystallogr. 1984, A40, C266; https://doi.org/10.1107/s0108767384092072.Suche in Google Scholar

Received: 2023-03-02
Accepted: 2023-03-24
Published Online: 2024-10-02
Published in Print: 2024-12-17

© 2023 the author(s), published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of 3-nitrophenol-2,1,3-benzoselenadiazole (1/1), C12H9N3O3Se
  4. Crystal structure of diaqua-(hydroxido)-{μ-[2-(hydroxy)-5-[(4-nitrophenyl)diazenyl]benzoato]}-{2-hydroxy-5-[(4-nitrophenyl)diazenyl]benzoato}-(1,10-phenanthroline)-diterbium hydrate, C38H27.4N8O12.2Tb
  5. Crystal structure of poly[bis(μ3-3-fluoro-4-(1H-1,2,4-triazol-1-yl)benzoato-κ3 O:O′:N)cadmium(II)] – dimethylformamide (1/1), C21H17CdF2N7O5
  6. The crystal structure of 2-amino-N-(pyridin-2-yl)benzamide, C12H11N3O
  7. The crystal structure of 2,3-di(pyridin-2-yl)-2,3-dihydroquinazolin-4(1H)-one, C18H14N4O
  8. Crystal structure of 2-chloro-4-fluorobenzyl (R)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H18ClFO3
  9. Crystal structure of [1-(4-carboxyphenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylic acid]-(methylsulfinyl)methane, C15H16N2O6S
  10. The crystal structure of 2-ethyl-1,1-dimethyl-1H-benzo[e]indole, C16H17N
  11. The crystal structure of (Z)-5-amino-N -hydroxy-1H-pyrazole-4-carboximidamide, C4H7N5O
  12. The crystal structure of 2,2,5-trimethyl-3-(4-(4-(5-phenyl-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)phenyl)imidazolidin-4-one, C24H24N4O2S
  13. The crystal structure of tetrakis(μ2-acetato-κ2 O:O′)-bis[(4′-phenyl-4,2′:6′,4″-terpyridine-κ1 N)dicopper(II)], C25H21CuN3O4
  14. Crystal structure of poly(3-thiophenecarboxylato-κ 3 O,O′:O′)-(methanol-κO)cadmium(II), C11H10O5S2Cd
  15. The crystal structure of dichloridobis[4′-(p-methoxylphenyl)-4,2′:6′,4″-terpyridine-κN] zinc(II), C44H34Cl2N6O2Zn
  16. The crystal structure of 1-(2-carboxyethyl)-1H-imidazole 3-oxide
  17. Crystal structure of 1,1′,1″-(nitrilotris(ethane-2,1-diyl))tris(3-(4-(((E)-pyridin-2-ylmethylene)amino)phenyl)urea), C45H47N13O4
  18. Crystal structure of a (E)-4-bromo-N-(4-(diethylamino)-2-hydroxybenzylidene) benzenaminium acetate ─ 4-bromoaniline (1/1)
  19. Crystal structure of 2,2′-(iminobis(methylene))bis(benzimidazolium) bis(p-toluenesulfonate), C30H31N5O6S2
  20. The crystal structure of alogliptinium meta-chlorobenzoate
  21. Crystal structure of 4-bromobenzyl 2-(6-methoxy-naphthalen-2-yl)propanoate, C21H19BrO3
  22. The hydrated double salt structure of (E)-4-(2-benzylidenehydrazine-1-carbonyl)pyridin-1-ium cation with 2-hydroxybenzoate and benzoate anions
  23. Crystal structure of (R)(R)-5-chloro-3-((S,1E,3E)-3,5-dimethyl-hepta-1,3-dien-1-yl)-7-methyl-6,8-dioxo-2,6,7,8-tetrahydroisoquinolin-7-yl acetate, C21H24ClNO4
  24. The crystal structure of bis(3-oxo-1,3-diphenylprop-1-en-1-olato-κ 2 O:O′)-bis(1,4-dioxane-κ 1 O)nickel(II), C38H38O8Ni
  25. Crystal structure of poly[aqua-(pyridine-3-carboxylato-κ1 N)(pyridine-3-carboxylato-κ2 O,O′) cadmium(II)] dihydrate, C12H14N2O7Cd
  26. The crystal structure of 4-(4-phenyl-5-(((1-(2,4,6-tribromophenyl)-1H-1,2,3-triazol-4-yl)methyl)thio)-4H-1,2,4-triazol-3-yl)pyridine, C22H14Br3N7S
  27. The crystal structure of N-benzylquinoline-2-carbothioamide, C17H14N2S
  28. Crystal structure of bis(3-isopropylphenyl)-4,4′-bipyridinium dichloride dihydrate, C28H30N2⋅2Cl⋅2H2O
  29. The crystal structure of ethyl 2-amino-4-(cyanophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C19H18N2O4
  30. Crystal structure of (4R,10S)-6-hydroxy-7-isopropyl-4,10-dimethyl-1,2,3,5-hexahydro-6,10-epoxyazulen-9-one, C15H22O3
  31. The crystal structure of (E)-(2-(2-hydroxy-3-methoxybenzylidene)aminophenyl)arsonic acid, C14H14AsNO5
  32. The crystal structure of poly[(μ 2-2-aminoisophthalato-κ4O,O′:O″:O″′)-(N-methylpyrrolidone κ1O)-dioxido-uranium(VI)], C13H14N2O7U
  33. The crystal structure of the co-crystal isonicotinamide · terephthalic acid, C8H6O4·2(C6H6N2O)
  34. The crystal structure of (E)-1-phenyl-3-(p-tolylthio)but-2-en-1-one, C17H16OS
  35. The crystal structure of 4,5-bis((Z)-chloro(hydroxyimino)methyl)-1H-imidazol-3-ium chloride monohydrate
  36. The crystal structure of 1,2-bis(4-(dimethylamino)phenyl)ethane-1,2-dione. C18H20N2O2
  37. Crystal structure of 2-chloro-4-fluorobenzyl 2-acetoxybenzoate, C16H12ClFO4
  38. Crystal structure of methyl 1-phenyl-9H-pyrido[3,4-b]indole-3-carboxylate, C19H14N2O2
  39. Crystal structure of (3-(dimethoxymethyl)-5-methoxy-1H-indol-1-yl)(5-fluoro-2-iodophenyl)methanone, C19H17FINO4
  40. Crystal structure of tetrachlorido-bis(1-[(1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2 N:N′)dicopper, C36H32Cu2N24Cl4
  41. Crystal structure of 2-(2,3-bis(4-methoxyphenyl)-1H-pyrrolo[2,3-b]quinoxalin-1-yl)anilin, C30H24N4O2
  42. Crystal structure of 5,7-dihydroxy-2-phenyl-4H-chromen-4-one–N,N-dimethylformamide(1/1), C18H17NO5
  43. The crystal structure of bis(μ 2-biphenyl-2,2′-dicarboxylato)-diaqua-bis(nitrato)-bis(2,2′:6′,2′′-terpyridine)dineodymium(III), C46H32I2N8Nd2O16
  44. Crystal structure of (Z)-4-amino-N -((4-chlorophenyl)(phenyl)methylene)benzohydrazide, C20H16ClN3O
  45. Crystal structure of (E)-6,8-dimethoxy-4-(4-morpholinobenzylidene)-3,4-dihydro-1-benzoxepin-5(2H)-one, C23H25NO5
  46. Crystal structure of (R)-2-((3-(3-aminopiperidin-1-yl)-6-methyl-5-oxo-1,2,4-triazin-4(5H)-yl) methyl)-4-fluorobenzonitrile benzoate monohydrate, C24H27FN6O4
  47. The crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylato-κ 3 N,O,O)copper(II)]monohydrate, C12H15NO9Cu
  48. Crystal structure of (((4-chlorophenyl)sulfonyl)glycinato-κ 2 N,O)bis(1,10-phenanthroline-κ 2 N,N′)cobalt(II) tetrahydrate, C32H30ClCoN5O8S
  49. Crystal structure of (((3-nitrophenyl)sulfonyl)-β-alaninato-κO)bis(2,2′-bipyridine-κ 2 N, N′)copper(II) 3-nitrobenzenesulfonate, C35H29CuN7O11S2
  50. Crystal structure of 3-phenoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C27H24O4
  51. 6-(2′,3′-Dihydroxy-3′-methylbutyl)-7-methoxy-8-(3″-methylbut-2″-en-1″-yl)-2H-chromen-2-one, C20H26O5
  52. Crystal structure of bromido-(2,2′:6′,2″-terpyridine-4′-onato-κ3N)palladium(II) methanol solvate
  53. The crystal structure of ethyl 2-amino-(4-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C20H22N2O6
  54. Crystal structure of (1E,3E,5E)-1,6-bis(4-(pentyloxy)phenyl)hexa-1,3,5-triene, C28H36O2
  55. The crystal structure of tris(2-bromo-4-methylphenyl)amine, C21H18Br3N
  56. The crystal structure of 3-(2,5-dimethylanilino)-1-(2,5-dimethylphenyl)-4-methyl-1H-pyrrole-2,5-dione, C21H22N2O2
  57. Crystal structure of dicarbonyl (μ2-indole-2-carboxylato κ2 O:O′)tris(triphenylarsine-κAs)dirhodium(I) acetone solvate, C68H56As3NO5Rh2
  58. The crystal structure of 4-chloro-2-formylphenyl 4-methylbenzenesulfonate, C14H11ClO4S
  59. Crystal structure of 4-iodobenzyl 2-(6-methoxynaphthalen-2-yl) propanoate, C21H19IO3
Heruntergeladen am 6.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2023-0098/html
Button zum nach oben scrollen