Abstract
C24H17NBr2, monoclinic, P21/n (no. 14), a = 9.6466(19) Å, b = 14.030(3) Å, c = 13.894(3) Å, β = 100.95(3)°, V = 1846.2(7) Å3, Z = 4, Rgt(F) = 0.0440, wRref(F2) = 0.0970, T = 173(2) 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.

Data collection and handling.
| Crystal: | Yellow block |
| Size: | 0.29 × 0.19 × 0.09 mm |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 4.40 mm−1 |
| Diffractometer, scan mode: | Rigaku, ω scan |
| θmax, completeness: | 27.5°, 99 % |
| N(hkl)measured, N(hkl)unique, Rint: | 12088, 4156, 0.059 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 3,808 |
| N(param)refined: | 265 |
| Programs: | Rigaku, 1 SHELX 2 , 3 |
1 Source of materials
The title compound was synthesized via 3-step reactions with commercially available 9,10-phenanthrenequinone and 2,6-diethylaniline as starting materials according to our previous report. 4 The 10-ethyl-14-methyldibenzo[a,c]acridine (synthesized by our previous report 4 ) (3.00 g, 9.34 mmol) was dissolved in CCl4 (100 mL) and N-bromosuccinimide (3.32 g, 18.68 mmol) and dibenzoyl peroxide (0.23 g, 10 mol %) were added to the above solutions. The suspension was stirred and heated to reflux in a vessel open to the air for 6 h. On completion of the reaction, the mixture was filtered whilst hot. The filtrate was collected and the solvent removed under reduced pressure. The residue was recrystallized from dichloromethane and heptane forming the title compound as a yellow solid (4.25 g, 95 %). Melting point: 174–175 °C. Yellow crystals of the title compound were obtained in a mixture of dichloromethane and diethyl ether.
2 Experimental details
The crystal data was collected, refined and reduced by CrystalClear (Rigaku Inc., 2007). 1 The crystal structure was solved using the SHELXTL 2 structure solution program and refined with the SHELXL 3 refinement package. All hydrogen atoms were placed in calculated positions and refined as riding on their parent atom. It is noted that there exists position disorder in 1-bromoethyl connected to the C21 of benzene ring due to the rotation of the terminal ethyl group. To solve this problem, the C24 and Br2 atoms from 1-bromoethyl were split to two sets with the site occupancy factors of 0.91766 (C24 and Br2) and 0.08234 (C24A and Br2A) and the related SIMU, ISOR and DFIX orders were used in the refinement.
3 Comment
The 9,10-phenanthrenequinone-based α-diimine compounds are an important class of organic ligands and used to synthesize the corresponding α--diimine nickel complexes for ethylene polymerization 5 , 6 , 7 or pincer palladium complexes for catalyzing coupling reactions. 4 In this paper, a molecule and its synthesis by 3-step reactions using commercially available 9,10-phenanthrenequinone and 2,6-diethylaniline as raw materials is described. 4 The title molecule features some geometric similarities to the aforementioned α-diimines.
The asymmetric unit of the title compound contains one independent molecule. It is a pentacyclic skeleton composing of phenanthrene-based fused quinoline heterocycle. There are 1-bromomethyl and bromoethyl in the 3- and 7-position of the quinoline ring, respectively. The bond lengths of N1–C14 and N1–C22 are 1.329(4) and 1.350(4) Å, respectively, which is typical for carbon-nitrogen double bond. 8 In addition, the bond lengths of C16–Br1 and C23–Br2 are 1.983(3) and 1.976(4) Å, respectively. The bond lengths and bond angels of the title structure lie in the normal range and are in accordance with the previous literatures. 4 , 9 , 10 The dihedral angle between the plane (C1/C2/C3/C4/C5/C6) of benzene ring and the plane (C13/C14/N1/C22/C17/C15) of pyridine ring is 7.15°. The dihedral angle of the plane (C7/C8/C9/C10/C11/C12) of benzene ring and the plane (C13/C14/N1/C22/C17/C15) of pyridine ring is 17.73°. The complete set of X-ray diffraction data for the title compound was deposited to the Cambridge Crystallographic Data Center (CCDC entry no. 2418020).
Funding source: Natural Science Foundation of China
Award Identifier / Grant number: 22461043
Funding source: Natural Science Foundation of China
Award Identifier / Grant number: 22261052
Funding source: National Undergraduate Training Program for Innovation and Entrepreneurship
Award Identifier / Grant number: 202410719048
Funding source: the Basic Science (chemistry & biology) Research Program of Shaanxi
Award Identifier / Grant number: 23JHQ020
Acknowledgements
We gratefully acknowledge the supports of Yan’an University.
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Conflict of interest: The authors declare no conflicts of interest regarding this article.
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Research funding: Natural Science Foundation of China (Program Nos. 22461043, 22261052); National Undergraduate Training Program for Innovation and Entrepreneurship (Program No. 202410719048) and the Basic Science (chemistry & biology) Research Program of Shaanxi (Program No. 23JHQ020).
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Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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.
Articles in the same Issue
- 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
Articles in the same Issue
- 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