Startseite Crystal structure of 2-bromo-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13BrFNO4S2
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Crystal structure of 2-bromo-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13BrFNO4S2

  • Wenhui Wu , Kun Xiao , Ji Wang ORCID logo , Qingchun Guo , Xiaoping Gao und Yaxian Qiu EMAIL logo
Veröffentlicht/Copyright: 24. April 2025

Abstract

C16H13BrFNO4S2, monoclinic, P21/c (no. 14), a = 9.1629(2) Å, b = 17.9824(4) Å, c = 10.3488(2) Å, β = 95.501(1)°, V = 1697.33(6) Å3, Z = 4, R gt (F) = 0.0331, wR ref (F2) = 0.0804, T = 150 K.

CCDC no.: 2440471

The molecular structure is shown in the figure. Table 1 contains the crystallographic data. The list of the atoms including atomic coordinates and displacement parameters can be found in the cif-file attached to this article.

1 Source of materials

A Pyrex reaction tube (100 mL) was prepared by oven-drying under a nitrogen atmosphere at 120 °C for 4 h to ensure complete removal of moisture. The reagents, 4-bromo-N-(2-ethynylphenyl)-N-methylbenzenesulfonamide (3 mmol, 1 equiv.), 2,4-difluoro-1-iodobenzene (12 mmol, 4 equiv.), di-tert-butyl sulfoxide (12 mmol, 4 equiv.), [Ir(dtbbpy)(ppy)2][PF6] (3 mol%, photoredox catalyst), and dichloromethane (15 mL, solvent) were added sequentially. The reaction vessel was sealed with a Teflon-lined cap and purged with nitrogen gas (3 min) to establish an inert atmosphere. The mixture was stirred magnetically at room temperature (25 °C) while exposed to blue light irradiation (λ = 350 nm, 30 W LED array) for 24 h. Upon reaction completion, the mixture was quenched by addition of ethyl acetate (20 mL × 3). The organic layers were separated, washed sequentially with saturated NaHCO3 solution (60 mL) and brine (60 mL), and dried over anhydrous MgSO4. After filtration, the solvent was removed under reduced pressure using a rotary evaporator. The crude product was purified via flash column chromatography (silica gel, 200–300 mesh, EtOAc/hexane 1:1). A portion of the purified material (0.1 g) was dissolved in EtOAc (10 mL) and slowly evaporated at ambient temperature to afford colorless crystals of the title compound.

Table 1:

Data collection and handling.

Crystal: Colourless block
Size: 0.13 × 0.09 × 0.07 mm
Wavelength: MoKα radiation (0.71073 Å)
μ: 2.70 mm−1
Diffractometer, scan mode: Bruker D8 VENTURE, φ and ω scans
θmax, completeness: 26.4°, 100 %
N(hkl)measured, N(hkl)unique, Rint: 19810, 3472, 0.061
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2,956
N(param)refined: 227
Programs: Bruker, 1 SHELX, 2 , 3 Olex2 4

2 Experimental details

The crystal structure of the title compound was determined using Mo-Kα radiation collected at 150 K on a Bruker D8 Venture diffractometer. 1 The initial phase solution was achieved in ShelXT, 2 followed by iterative model building and restrained least-squares refinement using ShelXL 3 within the Olex2 software platform. 4

3 Comment

Dioxodibenzothiazepines represent a class of fused heterocyclic compounds characterized by their conjugated benzene and thiazepine rings fused through oxygen and sulfur atoms, forming a rigid polycyclic scaffold. 5 These structures are of growing interest due to their unique electronic properties, such as enhanced π-conjugation and redox activity. 6 , 7 , 8 Such compounds serve as versatile platforms in medicinal chemistry (e.g., as calcium channel modulators) and materials science (e.g., organic semiconductors), where subtle structural modifications can drastically alter their biological activity and electronic behavior.

As illustrated in the figure, the compound features a fused dihydrodibenzo[c,f][1,2]thiazepine core, a benzothiazepine derivative. This fusion forms a bicyclic system comprising a seven-membered thiazepine ring and a six-membered benzene ring, consistent with structurally analogous compounds reported in literature. 9 , 10 , 11 , 12 , 13 The N1-nitrogen atom of the thiazepine ring is substituted with a methyl group (–CH3), while position 11 hosts a ((fluoromethyl) sulfonyl)methyl fragment introducing both sulfonyl –SO2 and –CH2F groups. The aromatic stability of the benzene rings and thiazepine ring is maintained through an alternating pattern of single and double bonds, with a C=C double bond contributing to planarity and electron delocalization.

In the solid state, the polycyclic framework is stabilized by specific intra-atomic interactions, wherein carbon atoms (C1–C16) form the backbone with C–C bond lengths ranging from 1.50 to 1.55 Å. Sulfur (S1) engages in double bonds (S=O) (1.45 Å) and single bonds (C–S) (1.82 Å). Bromine (Br1) is bonded via a weak aryl–C–Br linkage (2.00 Å), and flourine (F2) forms a short C–F bond (1.35 Å), confirming its incorporation within the sulfonyl-fluoromethyl substituent. Collectively, these structural features define the molecule’s electronic properties, reactivity profile, and potential applications in biological or material science contexts.


Corresponding author: Yaxian Qiu, Shanxi Police College, Taiyuan, Shanxi, China, E-mail:

Acknowledgments

This work was financially supported by China National Drug Control Research Center 2021: DR (2021) J011.

References

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Received: 2025-03-09
Accepted: 2025-04-02
Published Online: 2025-04-24
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
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  50. The crystal structure of bicyclol, C19H18O9
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  52. Crystal structure of 2,2-dichloro-N-methyl-N-(4-p-tolylthiazol-2-yl)acetamide, C13H12Cl2N2OS
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  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
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