Abstract
C14H8BrClN2, monoclinic, P21/n (no. 14), a = 17.1347(11) Å, b = 3.8441(2) Å, c = 18.4127(12) Å, β = 97.861(2)°, V = 1201.40(13) Å3, Z = 4, R gt (F) = 0.0388, wR ref (F2) = 0.1302, T = 170 K.
The molecular 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.

Data collection and handling.
Crystal: | Colorless block |
Size: | 0.15 × 0.11 × 0.08 mm |
Wavelength: | Mo Kα radiation (0.71073 Å) |
μ: | 3.62 mm−1 |
Diffractometer, scan mode: | D8 VENTURE, φ and ω |
θmax, completeness: | 26.5°, >99% |
N(hkl)measured, N(hkl)unique, Rint: | 12,671, 2469, 0.061 |
Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 1895 |
N(param)refined: | 163 |
Programs: | Bruker [1], SHELX [2, 3], Olex2 [4] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
Atom | X | y | z | Uiso*/Ueq |
---|---|---|---|---|
Br1 | 0.37170 (2) | 0.66309 (11) | 0.87227 (2) | 0.03856 (19) |
C1 | 0.4771 (2) | 0.5789 (10) | 0.7680 (2) | 0.0294 (8) |
H1 | 0.514521 | 0.682332 | 0.804515 | 0.035* |
C2 | 0.4994 (2) | 0.4754 (10) | 0.70059 (19) | 0.0273 (8) |
C3 | 0.4430 (2) | 0.3159 (9) | 0.64800 (19) | 0.0267 (8) |
C4 | 0.3647 (2) | 0.2718 (10) | 0.6626 (2) | 0.0327 (9) |
H4 | 0.326420 | 0.169797 | 0.626665 | 0.039* |
C5 | 0.3441 (2) | 0.3757 (9) | 0.7283 (2) | 0.0330 (9) |
H5 | 0.291675 | 0.344814 | 0.738596 | 0.040* |
C6 | 0.4015 (2) | 0.5294 (10) | 0.78053 (19) | 0.0296 (8) |
C7 | 0.5366 (2) | 0.2501 (10) | 0.5724 (2) | 0.0292 (8) |
H7 | 0.552724 | 0.172374 | 0.527811 | 0.035* |
C8 | 0.5938 (2) | 0.4167 (9) | 0.62477 (19) | 0.0251 (8) |
C9 | 0.6756 (2) | 0.4743 (10) | 0.60847 (19) | 0.0263 (8) |
C10 | 0.7310 (2) | 0.6244 (9) | 0.6621 (2) | 0.0278 (8) |
H10 | 0.715567 | 0.690231 | 0.707804 | 0.033* |
C11 | 0.8080 (2) | 0.6787 (10) | 0.6498 (2) | 0.0308 (8) |
H11 | 0.845049 | 0.784634 | 0.686239 | 0.037* |
C12 | 0.8301 (2) | 0.5763 (10) | 0.5835 (2) | 0.0296 (8) |
C13 | 0.7768 (2) | 0.4293 (11) | 0.5296 (2) | 0.0320 (9) |
H13 | 0.792527 | 0.364877 | 0.483959 | 0.038* |
C14 | 0.6996 (2) | 0.3756 (9) | 0.5424 (2) | 0.0306 (9) |
H14 | 0.662893 | 0.270396 | 0.505580 | 0.037* |
Cl1 | 0.92654 (6) | 0.6448 (3) | 0.56695 (6) | 0.0400 (3) |
N1 | 0.46344 (18) | 0.1985 (8) | 0.58250 (17) | 0.0292 (7) |
N2 | 0.57492 (17) | 0.5262 (8) | 0.68817 (15) | 0.0266 (7) |
Source of material
In a specific experiment, 1.86 g (10.0 mmol) 4-bromobenzene-1,2-diamine was initially dissolved in 40 mL toluene. About 1.55 g (11.0 mmol) 4-chlorobenzaldehyde was added to this solution and stirred for 5 min. Then 1.95 g (10.0 mmol) tosylmethyl isocyanide and 1.35 g (12.0 mmol) triethylene diamine were added. Subsequently, the mixture was heated to 80 °C and stirred for 4 h. The resulting solution was sequentially washed with hydrochloric acid (5%) and H2O. The organic compound was concentrated under reduced pressure and separated by silica-gel column chromatography with an ethyl acetate and petroleum ether (10%) mixture. Crystals obtained after slow evaporation of a combination of petroleum ether and ethyl acetate at room temperature within a week.
Experimental details
All hydrogen atoms were placed in calculated positions (C–H = 0.95 Å) and refined as riding atoms. The U iso values were constrained to be 1.2U eq . All the H atoms were refined as riding on their parent atom.
Comment
Quinoxaline, also known as benzopyrazine, is a bicyclic heterocyclic molecule composed of pyrazine and benzene rings. It has three other isomers, such as quinazoline, cinolin, and o-benzodiazine. Quinoxaline derivatives are widely used in industry [5, 6], dyes [7], [8], [9], and antibiotics [10], [11], [12]. They are essential in the industry because they can inhibit metal corrosion [5, 6]. And they can be used in dyes and electroluminescent materials because they have chromophores similar to natural systems. Additionally, they have attracted significant attention in the pharmacology industry because of their extensive biological characteristics. For example, they can fight against bacteria, fungi, viruses, Leishmania, tuberculosis, malaria, cancer, depression, and nervous activity. At present, many new compounds assembled with quinoxaline structure as precursors have been characterised [13], [14], [15], [16], [17], [18].
The asymmetric unit consists of one 7-bromo-2-(4-chloro-phenyl)-quinoxaline molecule. There is a bromine substituent bearing in the benzene ring of quinoxaline molecules, and the measured length of the C–Br bond is 1.901(4) Å. There is a chlorobenzene group substituted on the pyrazine ring at the para position of the chlorobenzene substituent, and the measured length of the C–C bond for C8–C9 is 1.490(6) Å. The size of the C–Cl bond in the chlorobenzene substituent is 1.741(4) Å. The two benzene rings are not entirely symmetrical. In the benzene ring of quinoxaline, the angle range of C–C–C is 119.1(4)–122.4(4)° with the minimum angle on the unsubstituted carbon atom and the maximum angle on the carbon atom with bromine substituent. In the benzene ring of chlorobenzene substituent, the angle range of C–C–C is 118.5(4)–121.2(4)° with the minimum angle on the carbon atom substituted by quinoxaline and the maximum angle on the carbon atom with chlorine substituent. C1⃛C6 and C9⃛C12 benzene rings are inclined to the average plane of heterocycles by 177.04(3)° and 176.5(3)° respectively, indicating that the styryl part is almost coplanar with the quinoline unit. For the given formula, all bond distances and angles are consistent with the expectation and in accord with the parent structure [19].
Funding source: Key Scientific Research Projects of Colleges and Universities in Henan Province http://dx.doi.org/10.13039/501100013066
Award Identifier / Grant number: 22A430032
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: This study was funded by the Key Scientific Research Projects of Colleges and Universities in Henan Province (22A430032).
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
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© 2022 Lilei Zhang and Tianyu Cheng, 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 {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4 N,N′,O,O′}copper(II) ─ diethylformamide (1/1), C23H23Br4CuN3O3
- The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
- Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
- Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
- Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
- The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
- Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
- The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
- The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
- Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
- The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
- Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
- The crystal structure of poly[diaqua-(μ2-1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ2N:N′)-bis(μ3-terephthalato-κ3O:O′:O′′)dicadmium(II)], C17H15N6O5Cd
- Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
- The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
- Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
- Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
- Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)nickel(II), C20H14N6NiS4
- The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
- The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
- The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
- The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
- Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O
- The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
- The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
- Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
- The crystal structure of (Z)-2-(4-(4-bromophenyl)thiazol-2-yl)-4-(3-hydroxybut-2-enoyl)-5-methyl -1,2-dihydro-3H-pyrazol-3-one – methanol (1/1), C18H18N3O4S
- Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
- The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
- The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
- The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
- Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
- The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
- The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
- The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
- Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
- Crystal structure of poly[diaqua-(μ3-fumarato)-(μ3-maleato)-(μ4-1,2,4,5-tetrakis((1H-1,2,4-triazol-1-yl)methyl)benzene)tetracadmium(II)] dihydrate, C34H32N12O9Cd4
- Crystal structure of a second modification of Pachypodol, C18H16O7
- Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
- The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
- The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
- The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
- Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
- The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
- Crystal structure of catena-poly[{μ2-3-carboxy-2,3-bis((4-methylbenzoyl)oxy)propanoato-κ2 O:O′}tris(methanol-κ1 O)lanthanum(III)], C63H63LaO27
Artikel in diesem Heft
- Frontmatter
- New Crystal Structures
- Crystal structure of {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4 N,N′,O,O′}copper(II) ─ diethylformamide (1/1), C23H23Br4CuN3O3
- The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
- Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
- Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
- Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
- The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
- Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
- The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
- The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
- Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
- The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
- Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
- The crystal structure of poly[diaqua-(μ2-1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ2N:N′)-bis(μ3-terephthalato-κ3O:O′:O′′)dicadmium(II)], C17H15N6O5Cd
- Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
- The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
- Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
- Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
- Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)nickel(II), C20H14N6NiS4
- The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
- The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
- The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
- The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
- Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O
- The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
- The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
- Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
- The crystal structure of (Z)-2-(4-(4-bromophenyl)thiazol-2-yl)-4-(3-hydroxybut-2-enoyl)-5-methyl -1,2-dihydro-3H-pyrazol-3-one – methanol (1/1), C18H18N3O4S
- Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
- The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
- The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
- The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
- Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
- The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
- The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
- The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
- Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
- Crystal structure of poly[diaqua-(μ3-fumarato)-(μ3-maleato)-(μ4-1,2,4,5-tetrakis((1H-1,2,4-triazol-1-yl)methyl)benzene)tetracadmium(II)] dihydrate, C34H32N12O9Cd4
- Crystal structure of a second modification of Pachypodol, C18H16O7
- Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
- The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
- The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
- The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
- Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
- The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
- Crystal structure of catena-poly[{μ2-3-carboxy-2,3-bis((4-methylbenzoyl)oxy)propanoato-κ2 O:O′}tris(methanol-κ1 O)lanthanum(III)], C63H63LaO27