Abstract
C13H7BrClF3N2, monoclinic, P21/c (no. 14), a = 9.4183(18) Å, b = 15.185(3) Å, c = 13.1826(18) Å, β = 133.905(8)°, V = 1358.4(4) Å3, Z = 4, R gt (F) = 0.0420, wR ref (F2) = 0.1015, T = 293 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: | Colourless block |
Size: | 0.23 × 0.20 × 0.18 mm |
Wavelength: | Mo Kα radiation (0.71073 Å) |
μ: | 3.25 mm−1 |
Diffractometer, scan mode: | Bruker APEX-II, φ and ω |
θmax, completeness: | 25.0°, >99 % |
N(hkl)measured, N(hkl)unique, Rint: | 6787, 2385, 0.037 |
Criterion for Iobs, N(hkl)gt: | Iobs > 2σ(Iobs), 1851 |
N(param)refined: | 182 |
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 | 1.10859 (5) | 0.65623 (3) | 0.70360 (4) | 0.05429 (18) |
C1 | 0.8392 (4) | 0.6293 (2) | 0.1822 (3) | 0.0336 (8) |
C2 | 0.6855 (5) | 0.6737 (2) | 0.0567 (4) | 0.0388 (8) |
H2A | 0.587817 | 0.701409 | 0.046158 | 0.047* |
C3 | 0.6790 (5) | 0.6764 (2) | −0.0509 (4) | 0.0401 (8) |
H3A | 0.576055 | 0.705277 | −0.134574 | 0.048* |
C4 | 0.8254 (5) | 0.6363 (2) | −0.0344 (4) | 0.0382 (8) |
C5 | 0.9785 (5) | 0.5947 (2) | 0.0883 (4) | 0.0439 (9) |
H5A | 1.078000 | 0.568977 | 0.099097 | 0.053* |
C6 | 0.9858 (5) | 0.5907 (2) | 0.1966 (4) | 0.0424 (8) |
H6A | 1.089953 | 0.561943 | 0.279885 | 0.051* |
C7 | 0.8520 (4) | 0.6248 (2) | 0.2995 (3) | 0.0331 (7) |
C8 | 1.0065 (4) | 0.6491 (2) | 0.4392 (3) | 0.0341 (7) |
C9 | 0.9507 (4) | 0.6318 (2) | 0.5123 (3) | 0.0339 (7) |
C10 | 0.7643 (4) | 0.59720 (19) | 0.4175 (3) | 0.0327 (7) |
C11 | 0.5218 (5) | 0.5535 (2) | 0.1602 (4) | 0.0494 (9) |
H11A | 0.415589 | 0.594638 | 0.115938 | 0.074* |
H11B | 0.494048 | 0.500988 | 0.184368 | 0.074* |
H11C | 0.535511 | 0.539026 | 0.096437 | 0.074* |
C12 | 1.1789 (5) | 0.6950 (2) | 0.4921 (4) | 0.0421 (8) |
C13 | 0.6322 (5) | 0.5702 (2) | 0.4360 (4) | 0.0450 (9) |
Cl1 | 0.81462 (16) | 0.63860 (7) | −0.17157 (10) | 0.0596 (3) |
F1 | 0.4589 (3) | 0.61039 (19) | 0.3446 (3) | 0.0721 (7) |
F2 | 0.5931 (4) | 0.48453 (16) | 0.4157 (3) | 0.0839 (8) |
F3 | 0.7063 (3) | 0.58747 (19) | 0.5621 (2) | 0.0760 (7) |
N1 | 0.7057 (4) | 0.59309 (16) | 0.2883 (3) | 0.0332 (6) |
N2 | 1.3138 (5) | 0.7340 (2) | 0.5339 (4) | 0.0688 (10) |
1 Source of materials
In a representative experiment 0.5 g (1.2 mmol) chlorfenapyr was dissolved in anhydrous dichloromethane, boron tribromide 0.4 g (1.5 mmol) was slowly dropped into the solution, and ethyl acetate and water were extracted to obtain 4-bromo-2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile. Under the catalysis of iron powder, the title compound was obtained by bromination of the above compounds twice. Crystals of the title compound were obtained by slow evaporation within 3 days in the mixed solution of ethyl acetate and n-hexane.
2 Experimental details
The collected diffraction data were then processed using the Bruker SAINT program [1], which applies standard corrections for absorption and decay of the X-ray source. The corrected data were then further analyzed using the SHELXT software suite to obtain the crystal structure [2]. The final refinement was performed using the Bruker SHELXL program [3], with the aid of the OLEX2 program for visualizing and refining the structure [4].
3 Comment
Aryl pyrrole insecticides and acaricides are commonly used pesticides with low toxicity, and the representative drug is chlorfenapyr [5]. The title compound is a key intermediate for the synthesis of chlorfenapyr, and it is of good significance to promote the scale production [6], [7], [8], [9] of chlorfenapyr.
The 4-bromo-2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile was synthesized and characterized through a combination of analytical methods [10]. There is one molecule in the asymmetric unit. The benzene ring and pyrrole ring are non-coplanar, with a dihedral angle of 54.32°. Several important bond angle data are involved as follows C1–C7–C8 = 129.1°, C1–C7–N1 = 124.3°.
The title compound has been reported for the first time in this paper. The geometric parameters are in the expected ranges [11].
Acknowledgments
This work was financially supported by the Hebei Provincial Natural Science Foundation of China (C2020209081). This work was financially supported by Beijing Zhongxingnuo Technology Co., Ltd.
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
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Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: Hebei Provincial Natural Science Foundation of China (C2020209081). This work was financially supported by Beijing Zhongxingnuo Technology Co., Ltd.
References
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© 2023 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 poly[diaqua-(μ4-3,3′-di(1H-1,2,4-triazol-1-yl)-[1,1′-biphenyl]-4,4′-dicarboxylate-N:N′:O:O′)cadmium(II)], C18H14N6O6Cd
- Crystal structure of (8R,8′S,13S,13′R)-8,8′-bis(hydroxymethyl)-9,9′,10,10′-tetramethoxy-5,5′,6,6′,8,8′,13,13′-octahydro-[13,13′-bi[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline]-7,7′-diium chloride-methanol (1/2), C46H58N2O14Cl2
- The crystal structure of 8-methoxy-2,2-diphenyl-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C29H25BN2O3S
- Crystal structure of aqua-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)copper(II) 5-carboxyisophthalate tetrahydrate, C25H50N4CuO11
- The crystal structure of 1-(naphthalen-2-ylsulfonyl)-2,2-diphenyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ij]quinoline, C31H23BN2O2S
- Crystal structure of iodido-(η6-benzene) (1-(pyridin-2-yl)-N-(p-fluoro-methanamine)-κ2N,Nʹ)ruthenium(II) hexaflourophosphate, (C18H15F7IN2RuP)
- The crystal structure of 1-(3-oxo-1-phenyl-3-(p-tolyl) propylidene)-1,3-dihydro-2H-inden-2-one, C25H20O2
- Crystal structure of tricyclohexyl[4-(4H-1,2,4-triazol-4-yl)-benzoato-κO]tin(IV), C27H39N3O2Sn
- Crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)cadmium(II)]monohydrate, C12H15NO9Cd
- Crystal structure of ethyl 2-((4-(3,5-dimethylisoxazol-4-yl)-2,6-difluorophenyl)amino)benzoate, C20H18F2N2O3
- The crystal structure of 2-(hydroxymethyl)-2-(4H-1,2,4-triazol-4-yl)propane-1,3-diol, C6H11N3O3
- The crystal structure of 1,2-bis(2,4-dinitrophenyl) hydrazine, C12H8N6O8
- Crystal structure of 1-(2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one, C19H14Cl2N2O3
- The crystal structure of 5-amino-5-oxo-4-(1-oxo-4-(2-oxopyrrolidin-1-yl)isoindolin-2-yl)pentanoic acid, C17H19N3O5
- Crystal structure of N2,N6-bis(2-(((Z)-5-bromo-2-hydroxybenzylidene)amino) phenyl)pyridine-2,6-dicarboxamide, C33H23Br2N5O4
- The crystal structure of (E)-2-methoxy-6-(((5-methyl-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C11H11N3O2S
- The crystal structure of 3-((tert-butyldiphenylsilyl)methyl)-5,5-diphenyl-6-(p-tolyl) tetrahydro-2H-pyran-2-one, C41H42O2Si
- Crystal structure of 9-fluoro-4-(6-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
- The crystal structure of 2-bromo-5-(4-cyanophenoxy)benzyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate, C21H19BrN2O3
- Crystal structure of 3,3′-(1,4-phenylenebis(methylene))bis(1-isopropyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C10H14F6N2P
- The crystal structure of 2,2-di(thiophen-3-yl)-1-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C24H19BN2O2S3
- Crystal structure of 5-bromo-1-(2-iodobenzoyl)-1H-indole-3-carbaldehyde, C16H9BrINO2
- The crystal structure of monocarbonyl-2-carboxypyridinato-κ2N,O-triphenylphosphine-rhodium(I) acetonitrile solvate, C26H20.50N1.50O3PRh
- Crystal structure of dichlorido-tetrakis(1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ1N)manganese(II), C60H68O4N12Cl10Mn
- Crystal structure of 3-(tert-butyldiphenylsilyl)-1-(2,6-dichlorophenyl)-2,2-diphenylpropan-1-ol, C37H36Cl2OSi
- Crystal structure of langite from Mine du Pradet (France)
- The crystal structure of 5′-(furan-2-yl)-3′-((4-methylphenyl)sulfonamido)-3′,4′,5′,6′-tetrahydro-[1,1′:3′,1″-terphenyl]-4′-carboxylic acid, C30H27NO5S
- Synthesis and crystal structure of bis{2-(((4-acetophenone)imino)methyl)-4-fluorophenolato-κ2N,O}zinc(II), C30H22F2N2O4Zn
- The crystal structure of poly[(tripyridine-κ3N,N′,N″) μ3-(pyridine-3,4-dicarboxylate-κ3N:O:O′) manganese(II)], C22H22N4O8Mn
- The crystal structure of (E)-4-chloro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15ClN2O2
- Synthesis and crystal structure of bis{2-(tert-butyl)-6-((E)-((4-((E)-1-(methoxyimino) ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II), C40H46CoN4O4
- Crystal structure of tetraaqua-[(1-(carboxymethyl)-1H-pyrazole-3-carboxylato-κ2N,O)cobalt(II)], C6H12CoN2O8
- (6R,7S)-2,3,13-trimethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3′,4′]cycloocta [1′,2′:4,5]benzo[1,2-d][1,3]dioxol-1-ol, C22H26O6
- Crystal structure of 2-((2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)amino)benzoic acid, C18H14Cl2N2O3
- Crystal structure of (5aS,6aS,8aR,9R,11aS, 11bS,13R,13aS)-1,1,8a,11a-tetramethyl-9-((S)-1-((S)-5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-3-oxo-1,7,8,8a,9,10,11,11a,11b,12,13,13a-dodecahydro-3H,6H-cyclopenta[5,6]cyclopropa[1,8a]naphtho[2,1-c]oxepin-13-yl acetate, C32H44O6
- Crystal structure of catena-poly[triaqua-(μ2-1-(4-carboxylatophenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylato-O,O′:O″)cobalt(II)], C12H12N2O8Co
- Crystal structure of 3-[(furan-2-ylmethyl)-amino]-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester, C17H13F4NO4
- Crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3-methoxybenzoate, C13H16O6
- Crystal structure of 4-bromo-2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, C13H7BrClF3N2
- The crystal structure of triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ3N,O,O)nickel(II) monohydrate, C12H15NO9Ni
- Crystal structure of dihydroxy(2,4,6-triisopro-pylphenyl)telluronium trifluoromethanesulfonate, C16H25F3O5STe
- The crystal structure of 1-(carboxymethyl)-1H-imidazole 3-oxide
- The crystal structure of 1,3,5-tris(dibromomethyl)benzene, C9H6Br6
- Crystal structure of (Z)-3-(4-methoxyphenyl)-4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-N-phenylthiazol-2(3H)-imine, C25H21N5OS
- Crystal structure of (Z)-3-(3-(4-hydroxyphenyl)-2-(phenylimino)-2,3-dihydrothiazol-4-yl)-2H-chromen-2-one, C24H16N2O3S
Artikel in diesem Heft
- Frontmatter
- New Crystal Structures
- Crystal structure of poly[diaqua-(μ4-3,3′-di(1H-1,2,4-triazol-1-yl)-[1,1′-biphenyl]-4,4′-dicarboxylate-N:N′:O:O′)cadmium(II)], C18H14N6O6Cd
- Crystal structure of (8R,8′S,13S,13′R)-8,8′-bis(hydroxymethyl)-9,9′,10,10′-tetramethoxy-5,5′,6,6′,8,8′,13,13′-octahydro-[13,13′-bi[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline]-7,7′-diium chloride-methanol (1/2), C46H58N2O14Cl2
- The crystal structure of 8-methoxy-2,2-diphenyl-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C29H25BN2O3S
- Crystal structure of aqua-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)copper(II) 5-carboxyisophthalate tetrahydrate, C25H50N4CuO11
- The crystal structure of 1-(naphthalen-2-ylsulfonyl)-2,2-diphenyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ij]quinoline, C31H23BN2O2S
- Crystal structure of iodido-(η6-benzene) (1-(pyridin-2-yl)-N-(p-fluoro-methanamine)-κ2N,Nʹ)ruthenium(II) hexaflourophosphate, (C18H15F7IN2RuP)
- The crystal structure of 1-(3-oxo-1-phenyl-3-(p-tolyl) propylidene)-1,3-dihydro-2H-inden-2-one, C25H20O2
- Crystal structure of tricyclohexyl[4-(4H-1,2,4-triazol-4-yl)-benzoato-κO]tin(IV), C27H39N3O2Sn
- Crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)cadmium(II)]monohydrate, C12H15NO9Cd
- Crystal structure of ethyl 2-((4-(3,5-dimethylisoxazol-4-yl)-2,6-difluorophenyl)amino)benzoate, C20H18F2N2O3
- The crystal structure of 2-(hydroxymethyl)-2-(4H-1,2,4-triazol-4-yl)propane-1,3-diol, C6H11N3O3
- The crystal structure of 1,2-bis(2,4-dinitrophenyl) hydrazine, C12H8N6O8
- Crystal structure of 1-(2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one, C19H14Cl2N2O3
- The crystal structure of 5-amino-5-oxo-4-(1-oxo-4-(2-oxopyrrolidin-1-yl)isoindolin-2-yl)pentanoic acid, C17H19N3O5
- Crystal structure of N2,N6-bis(2-(((Z)-5-bromo-2-hydroxybenzylidene)amino) phenyl)pyridine-2,6-dicarboxamide, C33H23Br2N5O4
- The crystal structure of (E)-2-methoxy-6-(((5-methyl-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C11H11N3O2S
- The crystal structure of 3-((tert-butyldiphenylsilyl)methyl)-5,5-diphenyl-6-(p-tolyl) tetrahydro-2H-pyran-2-one, C41H42O2Si
- Crystal structure of 9-fluoro-4-(6-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
- The crystal structure of 2-bromo-5-(4-cyanophenoxy)benzyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate, C21H19BrN2O3
- Crystal structure of 3,3′-(1,4-phenylenebis(methylene))bis(1-isopropyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C10H14F6N2P
- The crystal structure of 2,2-di(thiophen-3-yl)-1-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C24H19BN2O2S3
- Crystal structure of 5-bromo-1-(2-iodobenzoyl)-1H-indole-3-carbaldehyde, C16H9BrINO2
- The crystal structure of monocarbonyl-2-carboxypyridinato-κ2N,O-triphenylphosphine-rhodium(I) acetonitrile solvate, C26H20.50N1.50O3PRh
- Crystal structure of dichlorido-tetrakis(1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ1N)manganese(II), C60H68O4N12Cl10Mn
- Crystal structure of 3-(tert-butyldiphenylsilyl)-1-(2,6-dichlorophenyl)-2,2-diphenylpropan-1-ol, C37H36Cl2OSi
- Crystal structure of langite from Mine du Pradet (France)
- The crystal structure of 5′-(furan-2-yl)-3′-((4-methylphenyl)sulfonamido)-3′,4′,5′,6′-tetrahydro-[1,1′:3′,1″-terphenyl]-4′-carboxylic acid, C30H27NO5S
- Synthesis and crystal structure of bis{2-(((4-acetophenone)imino)methyl)-4-fluorophenolato-κ2N,O}zinc(II), C30H22F2N2O4Zn
- The crystal structure of poly[(tripyridine-κ3N,N′,N″) μ3-(pyridine-3,4-dicarboxylate-κ3N:O:O′) manganese(II)], C22H22N4O8Mn
- The crystal structure of (E)-4-chloro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15ClN2O2
- Synthesis and crystal structure of bis{2-(tert-butyl)-6-((E)-((4-((E)-1-(methoxyimino) ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II), C40H46CoN4O4
- Crystal structure of tetraaqua-[(1-(carboxymethyl)-1H-pyrazole-3-carboxylato-κ2N,O)cobalt(II)], C6H12CoN2O8
- (6R,7S)-2,3,13-trimethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3′,4′]cycloocta [1′,2′:4,5]benzo[1,2-d][1,3]dioxol-1-ol, C22H26O6
- Crystal structure of 2-((2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)amino)benzoic acid, C18H14Cl2N2O3
- Crystal structure of (5aS,6aS,8aR,9R,11aS, 11bS,13R,13aS)-1,1,8a,11a-tetramethyl-9-((S)-1-((S)-5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-3-oxo-1,7,8,8a,9,10,11,11a,11b,12,13,13a-dodecahydro-3H,6H-cyclopenta[5,6]cyclopropa[1,8a]naphtho[2,1-c]oxepin-13-yl acetate, C32H44O6
- Crystal structure of catena-poly[triaqua-(μ2-1-(4-carboxylatophenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylato-O,O′:O″)cobalt(II)], C12H12N2O8Co
- Crystal structure of 3-[(furan-2-ylmethyl)-amino]-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester, C17H13F4NO4
- Crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3-methoxybenzoate, C13H16O6
- Crystal structure of 4-bromo-2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, C13H7BrClF3N2
- The crystal structure of triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ3N,O,O)nickel(II) monohydrate, C12H15NO9Ni
- Crystal structure of dihydroxy(2,4,6-triisopro-pylphenyl)telluronium trifluoromethanesulfonate, C16H25F3O5STe
- The crystal structure of 1-(carboxymethyl)-1H-imidazole 3-oxide
- The crystal structure of 1,3,5-tris(dibromomethyl)benzene, C9H6Br6
- Crystal structure of (Z)-3-(4-methoxyphenyl)-4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-N-phenylthiazol-2(3H)-imine, C25H21N5OS
- Crystal structure of (Z)-3-(3-(4-hydroxyphenyl)-2-(phenylimino)-2,3-dihydrothiazol-4-yl)-2H-chromen-2-one, C24H16N2O3S