Startseite Crystal structure of phenyl(3,3-dichloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one)methanone, C7H4Cl2N2O
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Crystal structure of phenyl(3,3-dichloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one)methanone, C7H4Cl2N2O

  • Su-Fen Bai , Shan-Shan Li , Jia-Xuan Liu , Chun-Yu Tian , Xiao-Long Li und Xiao-Jin La EMAIL logo
Veröffentlicht/Copyright: 29. März 2023

Abstract

C7H4Cl2N2O, monoclinic, P21/c (no. 14), a = 6.215(2) Å, b = 16.544(5) Å, c = 8.561(3) Å, β = 108.707(4)°, V = 833.8(5) Å3, Z = 4, R gt (F) = 0.0339, wRref (F 2) = 0.1265, T = 296 K.

CCDC no.: 2133257

The molecular structure is shown in the figure (atoms are shown with arbitrary radii). Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colorless block
Size: 0.18 × 0.16 × 0.14 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.73 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 27.4°, >99%
N(hkl)measured, N(hkl)unique, R int: 4900, 1887, 0.020
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 1645
N(param)refined: 113
Programs: Bruker [1], SHELX [2, 3 2,3]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z U iso*/U eq
Cl1 0.37048 (8) 0.24819 (2) 0.82864 (6) 0.0503 (2)
Cl2 0.11395 (9) 0.37372 (3) 0.92705 (6) 0.0503 (2)
O1 0.6308 (2) 0.41342 (10) 0.96278 (14) 0.0528 (4)
N1 0.4736 (2) 0.44149 (9) 0.68521 (15) 0.0357 (3)
N2 0.2169 (2) 0.45036 (8) 0.40938 (15) 0.0319 (3)
C1 0.4863 (3) 0.40571 (10) 0.83112 (18) 0.0342 (4)
C2 0.2742 (3) 0.42094 (9) 0.56104 (17) 0.0280 (3)
C3 0.0139 (3) 0.42439 (10) 0.30775 (19) 0.0357 (4)
H1 −0.034451 0.443803 0.200121 0.043*
C4 0.2725 (3) 0.35021 (9) 0.79524 (18) 0.0309 (3)
C5 −0.1254 (3) 0.37144 (10) 0.3525 (2) 0.0408 (4)
H3 −0.263322 0.356152 0.276506 0.049*
C6 −0.0595 (3) 0.34049 (11) 0.5127 (2) 0.0382 (4)
H2 −0.149852 0.304094 0.546406 0.046*
C7 0.1461 (3) 0.36664 (8) 0.61830 (18) 0.0288 (3)
H1A 0.561 (5) 0.4834 (13) 0.666 (3) 0.078 (7)*

Source of material

To sodium hydride (0.44 g of 60 wt% NaH in oil, 0.011 mol) suspended in dry tetrahydrofuran (40 mL) at 0 °C under a nitrogen atmosphere was added 1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (1.34 g, 0.010 mol). The reaction mixture was stirred at room temperature for 30 min and then recooled to 0 °C. Then an excess of thionylchloride was added (2.91 mL, 0.040 mol). The resulting solution was warmed slowly to room temperature and stirred for 16 h. The solvent was removed with a rotary evaporator at 80 °C. The residue was extracted with ethyl acetate and saturated NaHCO3 solution. The organic layers were combined, and the solution was removed. The product was separated by column chromatography (petroleum ether: ethyl acetate = 7:2, v/v). Finally, the obtained solution was evaporated to dryness in vacuo and recrystallized from methanol and dichloromethane (2:1, v/v) to obtain the title compound as colorless block crystals.

Experimental details

All hydrogen atoms were placed in the calculated positions and constrained to ride on their parent atoms.

Comment

Azaindole is an important nitrogen-containing fused heterocycle in pharmaceutical chemistry [46]. Azaindoles exist as the basic structures of many natural botanicals and bioactive compounds [79], and are widely found in herbal medicines with therapeutic effects on diabetes.

In the molecules forming the title crystal structure, charasteristic bonds are C1–C4, C2–C7, and C5–C6. Their lengths are 1.562 (2) Å, 1.389 (2) Å, and 1.397 (2) Å respectively. The four C-N bond lengths range from 1.3240(19) Å for N2-C2 to 1.3919(19) Å for N1-C2. The bond lengths and angles are in the expected ranges [5, 6].


Corresponding author: Xiao-Jin La, College of Traditional Chinese Medicine, North China University of Science and Technology, Caofeidian District, 063210 Tangshan, P. R. China, E-mail:

Su-Fen Bai and Shan-Shan Li contributed equally.


Funding source: North China University of Science

Award Identifier / Grant number: KY201904005

Funding source: Tangshan Science and Technology Innovation Team Training Program

Award Identifier / Grant number: 19130205C

Funding source: Science and Technology Planning Project of Hebei Province

Award Identifier / Grant number: 14397705D

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work was supported by Hebei Key Laboratory of Integrated Traditional Chinese and Western Medicine for Diabetes and its Complications, College of Traditional Chinese Medicine, North China University of Science and Technology, 21 Bohai Road, Tangshan 063210, China. This work was supported by Science and Technology Partnership Program, Ministry of Science and Technology of China (KY201904005), Tangshan Science and Technology Innovation Team Training Program (19130205C) to Ji-an Li, Science and Technology Planning Project of Hebei Province, China (No. 14397705D).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2022-01-16
Accepted: 2022-02-21
Published Online: 2023-03-29
Published in Print: 2023-06-27

© 2022 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 phenyl(3,3-dichloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one)methanone, C7H4Cl2N2O
  4. Crystal structure of poly[diaqua-bis(μ 2-1,4-diaminobutane-N:N′)cobalt(II)] dichloride, C8H28Cl2CoN4O2
  5. Synthesis and crystal structure of (4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro-2H,6H-8a,4a-(epoxymethano)phenanthren-12-one, C20H32O3
  6. The crystal structure of 1-(2-chlorobenzyl)-3-(3,5-dichlorophenyl)urea, C14H11Cl3N2O
  7. Crystal structure of tetrapropylammonium-1,3,5-thiadiazole-5-amido-2-carbamate – 1,2,4-thiadiazole-3,5-diamine – water (1/1/1), C17H37N9O3S2
  8. Tetrabutylammonium 1,3,5-thiadiazole-5-amido-2-carbamate—1,2,4-thiadiazole-3,5-diamine— water (1/1/1), C21H45N9O3S2
  9. The crystal structure of ((E)-2,4-dichloro-6-(((2-hydroxy-5-nitrophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Cl2MnN5O4
  10. The crystal structure of aqua-bis{2-bromo-6-((2-(2-phenylacetyl)hydrazineylidene)methyl)phenolato-κ3 N,O,O′}-dimethylformamide-κ1 O-erbium(III) chloride – dimethylformamide – water (1/2/1), C39H49N7O9Br2ClEr
  11. Crystal structure of (diaqua-bis(phenanthroline-K 2 N,N′)-tetrakis(m 2-3,4,5,6-tetrafluorophthalato-K 4 O,O:O′:O″;K 2 O:O′)dierbium (III) phenanthroline (1/2), C80H38Er2F16N8O18
  12. Crystal structure of (E)-7-methoxy-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C20H17F3O3
  13. The crystal structure of 4–(4,4,5,5–tetramethyl–1,3,2–dioxaborolan–2–yl)morpholine, C10H20BNO3
  14. The crystal structure of catena–poly[aqua(1-naphthoato-κ 2 O,O′)-(μ-1-naphthoato-κ 4 O:O,O′:O′)lead(II)], C22H16O5Pb
  15. The crystal structure of 1-(4-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  16. The crystal structure of 4-(pyren-1-yl)butyl-4-nitrobenzoate, C27H21NO4
  17. Crystal structure of cyclo-(bis(µ2-3,3′-(1H-imidazole-3-ium-1,3-diyl)dipropionato-κ4 O,O′:O″,O″′)-dinitrato-κ2 O,O′-tetraoxido-diuranium(VI) C18H22N6O18U2
  18. The crystal structure of catena-[nitrato-κ 2 O,O′-(μ 3-3-iodobenzene-1,2-dicarboxylato-κ 4 O:O′:O″,O‴)-(2,2′:6′,2″-terpyridine-κ 3 N,N′,N″)lanthanum(III)], C23H14IN4O7La
  19. Redetermination of crystal structure of [bis(pyridin-2-ylmethyl)amine-κ 3 N,,]chloridopalladium(II) chloride monohydrate
  20. Crystal structure of catena-poly[triaqua-[bis(m2-4-(1H-1,2,4-triazol-1-yl)benzoato-k2O:O')-(4-(1H-1,2,4-triazol-1-yl)benzoato-k1O)-praseodymium (III) monohydrate], C27H26N9O10Pr
  21. Crystal structure of trans-diaqua-bis(methyl methylcarbamohydrazonothioato-κ2 N,N′) nickel(II) iodide semihydrate, C6H22N6O2NiS2I2·0.5H2O
  22. The crystal structure of 2-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoindolin-1-one, C17H13F4NOS
  23. The crystal structure of di-μ-1-naphthylacetato-κ 3 O,O′:O;κ 3 O:O,O′-bis[(1-naphthylacetato-κ 2 O,O′)(2,2′-bipyridine-κ 2 N,N′)lead(II)] monohydrate, C68H54N4O9Pb2
  24. Crystal structure of tetrapropylammonium guanidinium 4,4′-sulfonyldibenzoate monohydrate, C27H44N4O7S
  25. Crystal structure of bis(tetrapropylammonium) terephthalate – 1-(diaminomethylene)thiourea – water (1/2/4) C18H40N5O4S
  26. Crystal structure of (E)-7-fluoro-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C21H20FNO2
  27. The crystal structure of poly[diaqua-bis(μ 3-5-bromobenzene-1,3-dicarboxylato-κ 3 O,O,O′)-(μ 2-1,3-bis-(4-pyridyl)-propane-κ 2 N,N′)-dizinc(II))] – 5-bromobenzene-1,3-dicarboxylic acid [2/1], C37H29Br3N2O14Zn2
  28. The crystal structure of 2-bromo-1,3-phenylene bis(4-methylbenzenesulfonate), C20H17BrO6S2
  29. Crystal structure of europium dichromium icosaaluminum, EuCr2Al20
  30. The crystal structure of N1,N3-di((E)-benzylidene) isophthalohydrazide dihydrate, C 22 H 22 N 4 O 4
  31. Crystal structure of 7α,11α-dihydroxy-15-oxo-ent-kauran-16-en-19,6β-olide, C20H26O5
  32. Crystal structure of 4-chloro-N′-[(1E)-pyridin-3-ylmethylidene]benzohydrazide, C13H10ClN3O
  33. The crystal structure of (Z)-3-(1-(2-((E)-4-isopropylbenzylidene)hydrazinyl)ethylidene) chroman-2,4-dione, C21H20N2O3
  34. Crystal structure of E-7-fluoro-2-(2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C18H12F4O
  35. Crystal structure of bis(6-aminopyridine-2-carboxylato–k2O,N)-bis(N,N-dimethylformamide-k1 O)zinc(II), C18H24N6O6Zn
  36. Crystal structure of 5-(adamantan-1-yl)-3-[(4-{[2-(trifluoromethyl)phenyl]-methyl}piperazin-1-yl)methyl]-1,3,4-oxadiazole-2(3H)-thione, C25H31F3N4OS
  37. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea – water (2/2/1), C30H72N10O7S2
  38. Crystal structure of tris(2,2′-bipyridine-κ2 N,N′)iron(II) triiodide – dichloromethane (2/1), C61H50Cl2Fe2I12N12
  39. Crystal structure of 2-amino-3-[2-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-ethylideneamino]-but-2-enedinitrile, C17H17N5
  40. The crystal structure of 1-(2-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  41. Crystal structure of potassium bis(pentaselenido-κ 2 Se 1,Se 5)palladate(II), K2[Pd(Se5)2]
  42. The crystal structure of 5,10-bis(2-methoxyethyl)-5,10-dihydro-[1,2,3,4]tetrathiocino[5,6-b:8, 7-b′]diindole, C22H22N2O2S4
  43. The crystal structure of 4-(4-iodophenyl)-5H-1,2,3-dithiazole-5-thione, C8H4INS3
  44. Crystal structure of bis{μ2-(4-acetyl-phenoxy)acetato-κ2 O:O′}-bis{μ2-(4-acetyl-phenoxy)acetato-κ3 O,O′:O)- bis{(4-acetyl-phenoxy)acetato-κ2 O,O′}-bis(phenanthrolin-κ2 N,N′)didysprosium(III) tetrahydrate, C84H78N4O28Dy2
  45. Crystal structure of Eu2Pd3.37(1)Zn13.63(1)
  46. Crystal structure of 2-methoxy-4-(methoxy-carbonyl)phenyl 2-chloro-4-fluorobenzoate, C16H12ClFO5
  47. Crystal structure of catena-poly[bis(μ2-dicyanamide-κ2 N:N′)-bis(4-vinylpyridine-κN)-copper(II)], C18H14CuN8
  48. The crystal structure of iguratimod-dimethylformamide (1/1), C17H14N2O6S·C3H7NO
  49. Synthesis and crystal structure of 1-((3R,10S,13S,17S)-10,13-dimethyl-3-(m-tolylamino)hexadecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethan-1-one, C28H41NO
  50. The crystal structure of diaqua-bis(4-bromo-2-formylphenoxy)zinc(II), C14H12Br2O6Zn
  51. The crystal structure of tetra(1-ethylimidazole-κ 1 N)-[μ 4-imidazole-4,5-dicarboxylato-κ 4 O, N, O′, N′]-trioxido-divanadium, C25H33N10O7V2
  52. The crystal structure of (E)-N′-(1-(4-fluorophenyl)propylidene)-2-hydroxybenzohydrazide, C16H15FN2O2
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