Startseite Crystal structure of 6,11-dihydro-12H-benzo[e]indeno[1,2-b]oxepin-12-one, C17H12O2
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Crystal structure of 6,11-dihydro-12H-benzo[e]indeno[1,2-b]oxepin-12-one, C17H12O2

  • Yanqing Wang ORCID logo EMAIL logo , Hao Liu , Lin Wang , Huahao Li und Lintao Dong EMAIL logo
Veröffentlicht/Copyright: 2. April 2025

Abstract

C17H12O2, monoclinic, P21/c, a = 11.982(2) Å, b = 5.8563(11) Å, c = 17.894(3) Å, β = 99.892(4)°, V = 1237.0(4) Å3, Z = 4, Rgt(F) = 0.0506, wRref(F2) = 0.1221, T = 296.15 K.

CCDC no.: 2422913

1 Source of materials

The synthesis of 6,11-dihydro-12H-benzo[e]indeno[1,2-b]oxepin-12-one (DBIO) primarily referred to the literature of Jungang Wang and coworkers. 5 A reaction mixture containing 1,2-bis(bromomethyl)benzene (3.2 g, 12 mmol), 1H-indene-1,3(2H)-dione (1.5 g, 10 mmol), and Cs2CO3 (6.5 g, 20 mmol) was dissolved in DMSO (25 ml) and stirred at 80 °C for 12 h. Afterwards, the mixture was pouring into 250 ml of 1 M hydrochloric acid solution and subsequently extracted with ethyl acetate three times. The combined organic layers were dried using anhydrous sodium sulfate, filtered, and the solvent was evaporated to concentrate the mixture. The crude product was then purified via silica gel column chromatography using a petroleum ether/ethyl acetate eluent (40:1) to yield the final product as a yellow solid. To obtain the crystal of DBIO. A sample of DBIO (2.0 mmol) was transferred into a 20 ml glass tube containing a pre-mixed solvent composed of methanol and dichloromethane (10 ml, 1:1 v/v). The mixture was left for crystallization. After several days, well defined block crystals were isolated, washed with anhydrous methanol, and subsequently dried under air, yield 67 % (based on DBIO). The reagents and chemicals used in the synthesis were purchased from Anhui Zesheng Technology Co., Ltd.

Table 1:

Data collection and handling.

Crystal: Clear light colourless block
Size: 0.22 × 0.21 × 0.19 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.09 mm−1
Diffractometer, scan mode: Bruker SMART APEX2, φ and ω scans
θmax, completeness: 27.5°, 100 %
N(hkl)measured, N(hkl)unique, Rint: 7020, 2774, 0.039
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 1,649
N(param)refined: 172
Programs: Bruker, 1 Olex2, 2 SHELX 3 , 4

2 Experimental details

The crystal data obtained from the X-ray single-crystal diffractometer show excellent quality parameters. The initial structural determination of the title compound was achieved through the application of the intrinsic phasing method with the SHELXT program. Subsequent refinement was executed utilizing the SHELXL program (Table 1).

3 Comment

As an organic compound used as a pharmaceutical intermediate, the crystal structure of 6,11-dihydro-12H-benzo[e]indeno[1,2-b]oxepin-12-one (DBIO) has been reported in the literature. 5 However, the exploration of its crystalline forms is far from exhausted. In this work, we have successfully synthesized a new crystalline form of DBIO by optimizing the crystallization conditions. The crystal structure of this new form of DBIO is completely different from the previously reported structure. This result not only enriches the crystalline structural diversity of the compound but may also exhibit unique physical and chemical properties. For example, the change in crystal form may have a significant impact on the solubility, safety and stability of medicine, thereby providing new possibilities for its applications in pharmaceuticals and other fields. 6 , 7 , 8 The new DBIO crystal was obtained by slow solvent evaporation at room temperature. X-ray single-crystal structure determination reveals that the compound crystallizes in the monoclinic crystal system and belonging to the P21/c space group. The asymmetric unit comprises a complete DBIO molecule, with all atoms exhibiting full occupancy and no disorder observed. The C–C and C–O distances are of 1.340(2)–1.512(2) Å and 1.223(2)–1.340(2) Å, respectively. These bond lengths are similar to the reported isomeric DBIO crystal structure and crystals formed from structures analogous to DBIO. 9 , 10 , 11 , 12 , 13 The DBIO molecule can be regarded as consisting of two parts: a polycyclic structure (C1–C2–C3–C4–C5–C6–C7–C8–C9, including O1 and O2 connected to C7 and C9) and a benzene ring (C12–C13–C14–C15–C16–C17). These two parts are connected by C10 and C11, forming a certain angle, which ultimately results in the DBIO molecule not being a planar structure. Specifically, the angles of C8–C10–C17 and O1–C11–C12 are 111.295° and 112.937°, respectively. It is precisely this non-planar angular structure that enables the formation of isomers. Through calculations using the PLATON software and analysis with the Mercury software, 14 , 15 it is found that the aggregation of DBIO molecules in the DBIO crystal structure mainly relies on weak C–H⋯O interactions (C11–H11B⋯O2x, 1+y, z and C15–H15⋯O2x, −1/2−y, 1/2+z) and p-p stacking interactions. It is worth noting that the effective overlap between the aromatic rings of adjacent DBIO molecules is minimal, preventing the formation of classical face-to-face sandwich or T-shaped stacking. Instead, a parallel-displaced stacking with significant slippage between the centroids is formed. This type of stacking results in relatively weak π-π interactions, with the perpendicular distance between the aromatic rings ranging from 3.6142 to 3.6206 Å, and the slippage ranging from 2.446 to 2.736 Å. In the end, the DBIO molecules form a final three-dimensional framework through the weak attractive interactions mentioned above.


Corresponding authors: Yanqing Wang and Lintao Dong, College of Chemistry and Chemical Engineering, Weifang University, Weifang, Shandong 261061, P.R. China, E-mail: (Y. Wang), (L. Dong)

Acknowledgments

This work was supported by the Shandong Province Natural Science Foundation (No. ZR2021QB053), and research startup funds of Weifang University (No. 196100040020).

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Received: 2025-02-12
Accepted: 2025-03-21
Published Online: 2025-04-02
Published in Print: 2025-06-26

© 2025 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 5,5′-bis(2,4,6-trinitrophenyl)-2,2′-bi(1,3,4-oxadiazole), C16H4N10O14
  4. Crystal structure of catena-poly[(μ3-4,4′-oxydibenzoato- κ5 O,O: O,O:O)-bis(2,4,6-tri(3-pyridine)-1,3,5-triazine-κ1 N)cadmium(II)], C50H32CdN12O5
  5. The crystal structure of 1,4-diazepane-1,4-diium potassium trinitrate, C5H14KN5O9
  6. The crystal structure of benzyl 2,2,5,5-tetramethylthiazolidine-4-carboxylate, C15H21NO2S
  7. Crystal structure of 2-hydroxyethyl-triphenylphosphonium tetracyanidoborate, C24H20BN4OP
  8. The crystal structure of 1-methyl-3-(N-methylnitrous amide–N-methylene) imidazolidine-2,4,5-trione
  9. Crystal structure of N-((3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(2,2,2-trifluoroacetyl)-1H-pyrazol-5-yl)carbamoyl)-2,6-difluorobenzamide, C20H7Cl2F8N5O3S
  10. Crystal structure of 5-(2,2-difluoropropyl)-5-methylbenzo[4,5]imidazo[2,1-a] isoquinolin-6(5H)-one, C20H18F2N2O
  11. The crystal structure of N′,N″-[1,2-bis(4-chlorophenyl)ethane-1,2-diylidene]bis(furan-2- carbohydrazide), C24H16Cl2N4O4
  12. Crystal structure of [(4-bromobenzyl)triphenylphosphonium] tetrabromoantimony(III), [C25H21BrP]+[SbBr4]
  13. Crystal structure of [(4-bromobenzyl)triphenylphosphonium] tetrabromidoindium(III), [C25H21BrP]+[InBr4]
  14. The crystal structure of 4-carboxy-2-oxobutan-1-aminium chloride, C5H10ClNO3
  15. Crystal structure of (4-(4-chlorophenyl)-1H-pyrrole-3-carbonyl)ferrocene, C21H16ClFeNO
  16. The crystal structure of dichlorido(η6-p-cymene)(triphenylarsine)ruthenium(II), C28H29AsCl2Ru
  17. Crystal structure of (Z)-2-hydroxy-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H16N2O2
  18. The crystal structure of 10-(1-bromoethyl)-14-(bromomethyl)dibenzo[a, c]acridine, C24H17NBr2
  19. Synthesis and crystal structure of 6-methoxy-7-[(4-methoxyphenyl)methoxy]-2H-1-benzopyran-2-one, C18H16O5
  20. Synthesis and crystal structure of ethyl 4-((4-trifluoromethylbenzyl)amino)benzo, C17H16F3NO2
  21. The crystal structure of (Z)-2-(tert-butyl)-6-(7-(tert-butyl)-5-methylbenzo[d][1,3]oxathiol-2-ylidene)-4-methylcyclohexa-2,4-dien-1-one, C23H28O2S
  22. The crystal structure of (R)-2-aminobutanamide hydrochloride, C4H11ClN2O
  23. Crystal structure of bromido[hydridotris(3-tert-butyl-5-isopropylpyrazolyl)borato-κ3 N,N′,N″]copper(II), C30H52BBrCuN6
  24. Crystal structure of chlorido{hydridotris[3-mesityl-5-methyl-1H-pyrazol-1-yl-κN3]borato}-copper(II) dichloromethane monosolvate
  25. Crystal structure of 4-[3,5-bis(propan-2-yl)-1H-pyrazol-4-yl]pyridine, C14H19N3
  26. Crystal structure of ((4-(4-bromophenyl)-1H-pyrrol-3-yl)methyl)ferrocene, C21H16BrFeNO
  27. Crystal structure of [(4-chlorobenzyl)triphenylphosphonium] dichloridocopper(I), {[C25H21ClP]+[CuCl2]}n
  28. The crystal structure of {Cu(2,9-diisopropyl-4,7-diphenyl-1,10-phenanthroline)[4,5-bis(diphenylphosphino)-9,9-dimethylxanthene]}+ PF6·1.5(EtOAC)
  29. Crystal structure of 3,5-bis(t-butyl)-1H-pyrazol-4-amine, C11H21N3
  30. Crystal structure of [(2,4-dichlorobenzyl)triphenylphosphonium] trichloridocopper(II), [C25H20Cl2P]+[CuCl3]
  31. The crystal structure of dipotassium sulfide, K2S
  32. Crystal structure of (4-(4-methoxyphenyl)-1H-pyrrole-3-carbonyl)ferrocene, C22H19FeNO2
  33. Crystal structure of (E)-6-(4-methylpiperazin-1-yl)-2-(4-(trifluoromethyl)benzylidene)-3, 4-dihydronaphthalen-1(2H)-one, C23H23F3N2O
  34. Crystal structure of (E)-6-morpholino-2-(4-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H20F3NO2
  35. Crystal structure of Ce9Ir37Ge25
  36. The crystal structure of ethyl 6-(2-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylate, C14H11N3O4S
  37. Crystal structure of (4-(4-isopropylphenyl)-1H-pyrrol-3-yl)(ferrocenyl)methanone, C24H23FeNO
  38. Crystal structure of bis(methylammonium) tetrathiotungstate(VI), (CH3NH3)2[WS4]
  39. Crystal structure of 6,11-dihydro-12H-benzo[e]indeno[1,2-b]oxepin-12-one, C17H12O2
  40. Crystal structure of 3-[(4-phenylpiperidin-1-yl)methyl]-5-(thiophen-2-yl)-2,3-dihydro-1,3,4- oxadiazole-2-thione, C18H19N3OS2
  41. Crystal structure of N-isopropyl-1,8-naphthalimide C15H13NO2
  42. TiNiSi-type EuPdBi
  43. Crystal structure of 1-(p-tolylphenyl)-4-(2-thienoyl)-3-methyl-1H-pyrazol-5-ol, C16H14N2O2S
  44. The crystal structure of 3-(3-carboxypropyl)-2-nitro-1H-pyrrole 1-oxide, C7H9N3O5
  45. The crystal structure of tetraaqua-bis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetato-k2O:N)-tetrakis(2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetato-k1N)trizinc(II) hexahydrate C36H52N18O32Zn3
  46. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 4-hydroxy-3,5-dimethoxybenzoate monohydrate, C25H30FN3O9
  47. Crystal structure of bis(DL-1-carboxy-2-(1H-indol-3-yl)ethan-1-aminium) oxalate — acetic acid (1/2)
  48. Crystal structure of methyl (E)-4-((4-methylphenyl)sulfonamido)but-2-enoate, C12H15NO4S
  49. The crystal structure of actarit, C10H11NO3
  50. The crystal structure of bicyclol, C19H18O9
  51. The crystal structure of topiroxostat, C13H8N6
  52. Crystal structure of 2,2-dichloro-N-methyl-N-(4-p-tolylthiazol-2-yl)acetamide, C13H12Cl2N2OS
  53. Crystal structure of 4-(trifluoromethyl)-7-coumarinyl trifluoromethanesulfonate C11H4F6O5S
  54. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6)-((Z)-N,N′-bis(2-(dimethylamino)phenyl)carbamimidato-κ1N)potassium(I)
  55. Crystal structure of (Z)-2-(5-((4-(dimethylamino)naphthalen-1-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid, C18H16N2O3S2
  56. Crystal structure of (4-fluorobenzyl)triphenylphosphonium bromide, C25H21BrFP
  57. The crystal structure of dichlorido-[6-(pyridin-2-yl)phenanthridine-κ2N, N′]zinc(II)-chloroform (1/1), C19H13N2ZnCl5
  58. Crystal structure of (E)-(3-(2,4-dichlorophenyl)acryloyl)ferrocene, C19H14Cl2FeO
  59. The crystal structure of (E)-7-chloro-1-cyclopropyl-6-fluoro-3-((2-hydroxybenzylidene)amino)quinolin-4(1H)-one, C19H14ClFN2O2
  60. Crystal structure of 2-bromo-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13BrFNO4S2
  61. Crystal structure of 2-chloro-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13ClFNO4S2
  62. Crystal structure of 5-(2,2-difluoropropyl)-5-methyl-6-oxo-5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline-3-carbonitrile, C20H15F2N3O
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