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.
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.

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.
Acknowledgments
This work was financially supported by China National Drug Control Research Center 2021: DR (2021) J011.
References
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© 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
- Frontmatter
- New Crystal Structures
- Crystal structure of 5,5′-bis(2,4,6-trinitrophenyl)-2,2′-bi(1,3,4-oxadiazole), C16H4N10O14
- 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
- The crystal structure of 1,4-diazepane-1,4-diium potassium trinitrate, C5H14KN5O9
- The crystal structure of benzyl 2,2,5,5-tetramethylthiazolidine-4-carboxylate, C15H21NO2S
- Crystal structure of 2-hydroxyethyl-triphenylphosphonium tetracyanidoborate, C24H20BN4OP
- The crystal structure of 1-methyl-3-(N-methylnitrous amide–N-methylene) imidazolidine-2,4,5-trione
- 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
- Crystal structure of 5-(2,2-difluoropropyl)-5-methylbenzo[4,5]imidazo[2,1-a] isoquinolin-6(5H)-one, C20H18F2N2O
- The crystal structure of N′,N″-[1,2-bis(4-chlorophenyl)ethane-1,2-diylidene]bis(furan-2- carbohydrazide), C24H16Cl2N4O4
- Crystal structure of [(4-bromobenzyl)triphenylphosphonium] tetrabromoantimony(III), [C25H21BrP]+[SbBr4]−
- Crystal structure of [(4-bromobenzyl)triphenylphosphonium] tetrabromidoindium(III), [C25H21BrP]+[InBr4]−
- The crystal structure of 4-carboxy-2-oxobutan-1-aminium chloride, C5H10ClNO3
- Crystal structure of (4-(4-chlorophenyl)-1H-pyrrole-3-carbonyl)ferrocene, C21H16ClFeNO
- The crystal structure of dichlorido(η6-p-cymene)(triphenylarsine)ruthenium(II), C28H29AsCl2Ru
- Crystal structure of (Z)-2-hydroxy-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H16N2O2
- The crystal structure of 10-(1-bromoethyl)-14-(bromomethyl)dibenzo[a, c]acridine, C24H17NBr2
- Synthesis and crystal structure of 6-methoxy-7-[(4-methoxyphenyl)methoxy]-2H-1-benzopyran-2-one, C18H16O5
- Synthesis and crystal structure of ethyl 4-((4-trifluoromethylbenzyl)amino)benzo, C17H16F3NO2
- 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
- The crystal structure of (R)-2-aminobutanamide hydrochloride, C4H11ClN2O
- Crystal structure of bromido[hydridotris(3-tert-butyl-5-isopropylpyrazolyl)borato-κ3 N,N′,N″]copper(II), C30H52BBrCuN6
- Crystal structure of chlorido{hydridotris[3-mesityl-5-methyl-1H-pyrazol-1-yl-κN3]borato}-copper(II) dichloromethane monosolvate
- Crystal structure of 4-[3,5-bis(propan-2-yl)-1H-pyrazol-4-yl]pyridine, C14H19N3
- Crystal structure of ((4-(4-bromophenyl)-1H-pyrrol-3-yl)methyl)ferrocene, C21H16BrFeNO
- Crystal structure of [(4-chlorobenzyl)triphenylphosphonium] dichloridocopper(I), {[C25H21ClP]+[CuCl2]−}n
- 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)
- Crystal structure of 3,5-bis(t-butyl)-1H-pyrazol-4-amine, C11H21N3
- Crystal structure of [(2,4-dichlorobenzyl)triphenylphosphonium] trichloridocopper(II), [C25H20Cl2P]+[CuCl3]−
- The crystal structure of dipotassium sulfide, K2S
- Crystal structure of (4-(4-methoxyphenyl)-1H-pyrrole-3-carbonyl)ferrocene, C22H19FeNO2
- Crystal structure of (E)-6-(4-methylpiperazin-1-yl)-2-(4-(trifluoromethyl)benzylidene)-3, 4-dihydronaphthalen-1(2H)-one, C23H23F3N2O
- Crystal structure of (E)-6-morpholino-2-(4-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H20F3NO2
- Crystal structure of Ce9Ir37Ge25
- The crystal structure of ethyl 6-(2-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylate, C14H11N3O4S
- Crystal structure of (4-(4-isopropylphenyl)-1H-pyrrol-3-yl)(ferrocenyl)methanone, C24H23FeNO
- Crystal structure of bis(methylammonium) tetrathiotungstate(VI), (CH3NH3)2[WS4]
- Crystal structure of 6,11-dihydro-12H-benzo[e]indeno[1,2-b]oxepin-12-one, C17H12O2
- Crystal structure of 3-[(4-phenylpiperidin-1-yl)methyl]-5-(thiophen-2-yl)-2,3-dihydro-1,3,4- oxadiazole-2-thione, C18H19N3OS2
- Crystal structure of N-isopropyl-1,8-naphthalimide C15H13NO2
- TiNiSi-type EuPdBi
- Crystal structure of 1-(p-tolylphenyl)-4-(2-thienoyl)-3-methyl-1H-pyrazol-5-ol, C16H14N2O2S
- The crystal structure of 3-(3-carboxypropyl)-2-nitro-1H-pyrrole 1-oxide, C7H9N3O5
- 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
- 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
- Crystal structure of bis(DL-1-carboxy-2-(1H-indol-3-yl)ethan-1-aminium) oxalate — acetic acid (1/2)
- Crystal structure of methyl (E)-4-((4-methylphenyl)sulfonamido)but-2-enoate, C12H15NO4S
- The crystal structure of actarit, C10H11NO3
- The crystal structure of bicyclol, C19H18O9
- The crystal structure of topiroxostat, C13H8N6
- Crystal structure of 2,2-dichloro-N-methyl-N-(4-p-tolylthiazol-2-yl)acetamide, C13H12Cl2N2OS
- Crystal structure of 4-(trifluoromethyl)-7-coumarinyl trifluoromethanesulfonate C11H4F6O5S
- Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6)-((Z)-N,N′-bis(2-(dimethylamino)phenyl)carbamimidato-κ1N)potassium(I)
- Crystal structure of (Z)-2-(5-((4-(dimethylamino)naphthalen-1-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid, C18H16N2O3S2
- Crystal structure of (4-fluorobenzyl)triphenylphosphonium bromide, C25H21BrFP
- The crystal structure of dichlorido-[6-(pyridin-2-yl)phenanthridine-κ2N, N′]zinc(II)-chloroform (1/1), C19H13N2ZnCl5
- Crystal structure of (E)-(3-(2,4-dichlorophenyl)acryloyl)ferrocene, C19H14Cl2FeO
- The crystal structure of (E)-7-chloro-1-cyclopropyl-6-fluoro-3-((2-hydroxybenzylidene)amino)quinolin-4(1H)-one, C19H14ClFN2O2
- Crystal structure of 2-bromo-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13BrFNO4S2
- Crystal structure of 2-chloro-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13ClFNO4S2
- Crystal structure of 5-(2,2-difluoropropyl)-5-methyl-6-oxo-5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline-3-carbonitrile, C20H15F2N3O
Artikel in diesem Heft
- Frontmatter
- New Crystal Structures
- Crystal structure of 5,5′-bis(2,4,6-trinitrophenyl)-2,2′-bi(1,3,4-oxadiazole), C16H4N10O14
- 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
- The crystal structure of 1,4-diazepane-1,4-diium potassium trinitrate, C5H14KN5O9
- The crystal structure of benzyl 2,2,5,5-tetramethylthiazolidine-4-carboxylate, C15H21NO2S
- Crystal structure of 2-hydroxyethyl-triphenylphosphonium tetracyanidoborate, C24H20BN4OP
- The crystal structure of 1-methyl-3-(N-methylnitrous amide–N-methylene) imidazolidine-2,4,5-trione
- 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
- Crystal structure of 5-(2,2-difluoropropyl)-5-methylbenzo[4,5]imidazo[2,1-a] isoquinolin-6(5H)-one, C20H18F2N2O
- The crystal structure of N′,N″-[1,2-bis(4-chlorophenyl)ethane-1,2-diylidene]bis(furan-2- carbohydrazide), C24H16Cl2N4O4
- Crystal structure of [(4-bromobenzyl)triphenylphosphonium] tetrabromoantimony(III), [C25H21BrP]+[SbBr4]−
- Crystal structure of [(4-bromobenzyl)triphenylphosphonium] tetrabromidoindium(III), [C25H21BrP]+[InBr4]−
- The crystal structure of 4-carboxy-2-oxobutan-1-aminium chloride, C5H10ClNO3
- Crystal structure of (4-(4-chlorophenyl)-1H-pyrrole-3-carbonyl)ferrocene, C21H16ClFeNO
- The crystal structure of dichlorido(η6-p-cymene)(triphenylarsine)ruthenium(II), C28H29AsCl2Ru
- Crystal structure of (Z)-2-hydroxy-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H16N2O2
- The crystal structure of 10-(1-bromoethyl)-14-(bromomethyl)dibenzo[a, c]acridine, C24H17NBr2
- Synthesis and crystal structure of 6-methoxy-7-[(4-methoxyphenyl)methoxy]-2H-1-benzopyran-2-one, C18H16O5
- Synthesis and crystal structure of ethyl 4-((4-trifluoromethylbenzyl)amino)benzo, C17H16F3NO2
- 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
- The crystal structure of (R)-2-aminobutanamide hydrochloride, C4H11ClN2O
- Crystal structure of bromido[hydridotris(3-tert-butyl-5-isopropylpyrazolyl)borato-κ3 N,N′,N″]copper(II), C30H52BBrCuN6
- Crystal structure of chlorido{hydridotris[3-mesityl-5-methyl-1H-pyrazol-1-yl-κN3]borato}-copper(II) dichloromethane monosolvate
- Crystal structure of 4-[3,5-bis(propan-2-yl)-1H-pyrazol-4-yl]pyridine, C14H19N3
- Crystal structure of ((4-(4-bromophenyl)-1H-pyrrol-3-yl)methyl)ferrocene, C21H16BrFeNO
- Crystal structure of [(4-chlorobenzyl)triphenylphosphonium] dichloridocopper(I), {[C25H21ClP]+[CuCl2]−}n
- 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)
- Crystal structure of 3,5-bis(t-butyl)-1H-pyrazol-4-amine, C11H21N3
- Crystal structure of [(2,4-dichlorobenzyl)triphenylphosphonium] trichloridocopper(II), [C25H20Cl2P]+[CuCl3]−
- The crystal structure of dipotassium sulfide, K2S
- Crystal structure of (4-(4-methoxyphenyl)-1H-pyrrole-3-carbonyl)ferrocene, C22H19FeNO2
- Crystal structure of (E)-6-(4-methylpiperazin-1-yl)-2-(4-(trifluoromethyl)benzylidene)-3, 4-dihydronaphthalen-1(2H)-one, C23H23F3N2O
- Crystal structure of (E)-6-morpholino-2-(4-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H20F3NO2
- Crystal structure of Ce9Ir37Ge25
- The crystal structure of ethyl 6-(2-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylate, C14H11N3O4S
- Crystal structure of (4-(4-isopropylphenyl)-1H-pyrrol-3-yl)(ferrocenyl)methanone, C24H23FeNO
- Crystal structure of bis(methylammonium) tetrathiotungstate(VI), (CH3NH3)2[WS4]
- Crystal structure of 6,11-dihydro-12H-benzo[e]indeno[1,2-b]oxepin-12-one, C17H12O2
- Crystal structure of 3-[(4-phenylpiperidin-1-yl)methyl]-5-(thiophen-2-yl)-2,3-dihydro-1,3,4- oxadiazole-2-thione, C18H19N3OS2
- Crystal structure of N-isopropyl-1,8-naphthalimide C15H13NO2
- TiNiSi-type EuPdBi
- Crystal structure of 1-(p-tolylphenyl)-4-(2-thienoyl)-3-methyl-1H-pyrazol-5-ol, C16H14N2O2S
- The crystal structure of 3-(3-carboxypropyl)-2-nitro-1H-pyrrole 1-oxide, C7H9N3O5
- 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
- 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
- Crystal structure of bis(DL-1-carboxy-2-(1H-indol-3-yl)ethan-1-aminium) oxalate — acetic acid (1/2)
- Crystal structure of methyl (E)-4-((4-methylphenyl)sulfonamido)but-2-enoate, C12H15NO4S
- The crystal structure of actarit, C10H11NO3
- The crystal structure of bicyclol, C19H18O9
- The crystal structure of topiroxostat, C13H8N6
- Crystal structure of 2,2-dichloro-N-methyl-N-(4-p-tolylthiazol-2-yl)acetamide, C13H12Cl2N2OS
- Crystal structure of 4-(trifluoromethyl)-7-coumarinyl trifluoromethanesulfonate C11H4F6O5S
- Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6)-((Z)-N,N′-bis(2-(dimethylamino)phenyl)carbamimidato-κ1N)potassium(I)
- Crystal structure of (Z)-2-(5-((4-(dimethylamino)naphthalen-1-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid, C18H16N2O3S2
- Crystal structure of (4-fluorobenzyl)triphenylphosphonium bromide, C25H21BrFP
- The crystal structure of dichlorido-[6-(pyridin-2-yl)phenanthridine-κ2N, N′]zinc(II)-chloroform (1/1), C19H13N2ZnCl5
- Crystal structure of (E)-(3-(2,4-dichlorophenyl)acryloyl)ferrocene, C19H14Cl2FeO
- The crystal structure of (E)-7-chloro-1-cyclopropyl-6-fluoro-3-((2-hydroxybenzylidene)amino)quinolin-4(1H)-one, C19H14ClFN2O2
- Crystal structure of 2-bromo-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13BrFNO4S2
- Crystal structure of 2-chloro-11-(((fluoromethyl)sulfonyl)methyl)-6-methyl-6,11-dihydrodibenzo[c,f][1,2]thiazepine 5,5-dioxide, C16H13ClFNO4S2
- Crystal structure of 5-(2,2-difluoropropyl)-5-methyl-6-oxo-5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline-3-carbonitrile, C20H15F2N3O