Synthesis and structure of 6-bromo-2-(diethoxy-methyl)-2-hydroxy-3-phenyl-2,3-dihydro-1Himidazo[1,2-a]pyridin-4-ium chloride acetonitrile monosolvate

Firudin I. Guseinov; Aida I. Samigullina; Tuncer Hökelek; Sahil Z. Hamidov; Jamal Lasri; Khudayar I. Hasanov; Tahir A. Javadzade; Alebel N. Belay

doi:10.1107/S2056989025005778

Synthesis and structure of 6-bromo-2-(diethoxy-methyl)-2-hydroxy-3-phenyl-2,3-dihydro-1Himidazo[1,2-a]pyridin-4-ium chloride acetonitrile monosolvate

Firudin I. Guseinov
, Aida I. Samigullina
, Tuncer Hökelek
, Sahil Z. Hamidov
, Jamal Lasri
, Khudayar I. Hasanov
, Tahir A. Javadzade
, Alebel N. Belay

Hacettepe University

Research output: Contribution to journal › Article › peer-review

Abstract

In the title solvated molecular salt, C₁₈H₂₂BrN₂O₃⁺·Cl^- ·CH₃CN, the imidazole ring is in envelope conformation and the pyridine and phenyl rings are oriented at a dihedral angle of 72.52 (5)^°. In the crystal, O—H· · ·Cl and N—H· · ·Cl hydrogen bonds link the cations and anions into centrosymmetric tetramers enclosing R²₄(12) loops. Short Br· · ·Cl [3.2313 (4) A^̊] and O· · ·Cl [3.0490 (10) A^̊] contacts are observed. A Hirshfeld surface analysis of the structure indicates that the most important contributions for the crystal packing are from H· · ·H (52.4%), H· · ·C/C· · ·H (12.1%), H· · ·Br/Br· · ·H (11.0%) and H· · ·Cl/Cl· · ·H (10.2%) interactions.

Original language	English
Pages (from-to)	672-675
Number of pages	4
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	81
Issue number	Pt 8
DOIs	https://doi.org/10.1107/S2056989025005778
Publication status	Published - 1 Aug 2025

Keywords

crystal structure
hydrogen bond
imidazole
non-covalent interactions

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10.1107/S2056989025005778

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Guseinov, F. I., Samigullina, A. I., Hökelek, T., Hamidov, S. Z., Lasri, J., Hasanov, K. I., Javadzade, T. A., & Belay, A. N. (2025). Synthesis and structure of 6-bromo-2-(diethoxy-methyl)-2-hydroxy-3-phenyl-2,3-dihydro-1Himidazo[1,2-a]pyridin-4-ium chloride acetonitrile monosolvate. Acta Crystallographica Section E: Crystallographic Communications, 81(Pt 8), 672-675. https://doi.org/10.1107/S2056989025005778

@article{732a46c04d814ffc9386ca14b1bbbb75,

title = "Synthesis and structure of 6-bromo-2-(diethoxy-methyl)-2-hydroxy-3-phenyl-2,3-dihydro-1Himidazo[1,2-a]pyridin-4-ium chloride acetonitrile monosolvate",

abstract = "In the title solvated molecular salt, C18H22BrN2O3+·Cl- ·CH3CN, the imidazole ring is in envelope conformation and the pyridine and phenyl rings are oriented at a dihedral angle of 72.52 (5)°. In the crystal, O—H· · ·Cl and N—H· · ·Cl hydrogen bonds link the cations and anions into centrosymmetric tetramers enclosing R24(12) loops. Short Br· · ·Cl [3.2313 (4) Å] and O· · ·Cl [3.0490 (10) Å] contacts are observed. A Hirshfeld surface analysis of the structure indicates that the most important contributions for the crystal packing are from H· · ·H (52.4\%), H· · ·C/C· · ·H (12.1\%), H· · ·Br/Br· · ·H (11.0\%) and H· · ·Cl/Cl· · ·H (10.2\%) interactions.",

keywords = "crystal structure, hydrogen bond, imidazole, non-covalent interactions",

author = "Guseinov, \{Firudin I.\} and Samigullina, \{Aida I.\} and Tuncer H{\"o}kelek and Hamidov, \{Sahil Z.\} and Jamal Lasri and Hasanov, \{Khudayar I.\} and Javadzade, \{Tahir A.\} and Belay, \{Alebel N.\}",

year = "2025",

month = aug,

day = "1",

doi = "10.1107/S2056989025005778",

language = "English",

volume = "81",

pages = "672--675",

journal = "Acta Crystallographica Section E: Crystallographic Communications",

issn = "2056-9890",

publisher = "International Union of Crystallography",

number = "Pt 8",

}

Guseinov, FI, Samigullina, AI, Hökelek, T, Hamidov, SZ, Lasri, J, Hasanov, KI, Javadzade, TA & Belay, AN 2025, 'Synthesis and structure of 6-bromo-2-(diethoxy-methyl)-2-hydroxy-3-phenyl-2,3-dihydro-1Himidazo[1,2-a]pyridin-4-ium chloride acetonitrile monosolvate', Acta Crystallographica Section E: Crystallographic Communications, vol. 81, no. Pt 8, pp. 672-675. https://doi.org/10.1107/S2056989025005778

Synthesis and structure of 6-bromo-2-(diethoxy-methyl)-2-hydroxy-3-phenyl-2,3-dihydro-1Himidazo[1,2-a]pyridin-4-ium chloride acetonitrile monosolvate. / Guseinov, Firudin I.; Samigullina, Aida I.; Hökelek, Tuncer et al.
In: Acta Crystallographica Section E: Crystallographic Communications, Vol. 81, No. Pt 8, 01.08.2025, p. 672-675.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis and structure of 6-bromo-2-(diethoxy-methyl)-2-hydroxy-3-phenyl-2,3-dihydro-1Himidazo[1,2-a]pyridin-4-ium chloride acetonitrile monosolvate

AU - Guseinov, Firudin I.

AU - Samigullina, Aida I.

AU - Hökelek, Tuncer

AU - Hamidov, Sahil Z.

AU - Lasri, Jamal

AU - Hasanov, Khudayar I.

AU - Javadzade, Tahir A.

AU - Belay, Alebel N.

PY - 2025/8/1

Y1 - 2025/8/1

N2 - In the title solvated molecular salt, C18H22BrN2O3+·Cl- ·CH3CN, the imidazole ring is in envelope conformation and the pyridine and phenyl rings are oriented at a dihedral angle of 72.52 (5)°. In the crystal, O—H· · ·Cl and N—H· · ·Cl hydrogen bonds link the cations and anions into centrosymmetric tetramers enclosing R24(12) loops. Short Br· · ·Cl [3.2313 (4) Å] and O· · ·Cl [3.0490 (10) Å] contacts are observed. A Hirshfeld surface analysis of the structure indicates that the most important contributions for the crystal packing are from H· · ·H (52.4%), H· · ·C/C· · ·H (12.1%), H· · ·Br/Br· · ·H (11.0%) and H· · ·Cl/Cl· · ·H (10.2%) interactions.

AB - In the title solvated molecular salt, C18H22BrN2O3+·Cl- ·CH3CN, the imidazole ring is in envelope conformation and the pyridine and phenyl rings are oriented at a dihedral angle of 72.52 (5)°. In the crystal, O—H· · ·Cl and N—H· · ·Cl hydrogen bonds link the cations and anions into centrosymmetric tetramers enclosing R24(12) loops. Short Br· · ·Cl [3.2313 (4) Å] and O· · ·Cl [3.0490 (10) Å] contacts are observed. A Hirshfeld surface analysis of the structure indicates that the most important contributions for the crystal packing are from H· · ·H (52.4%), H· · ·C/C· · ·H (12.1%), H· · ·Br/Br· · ·H (11.0%) and H· · ·Cl/Cl· · ·H (10.2%) interactions.

KW - crystal structure

KW - hydrogen bond

KW - imidazole

KW - non-covalent interactions

UR - https://www.scopus.com/pages/publications/105012841302

U2 - 10.1107/S2056989025005778

DO - 10.1107/S2056989025005778

M3 - Article

C2 - 40777527

AN - SCOPUS:105012841302

SN - 2056-9890

VL - 81

SP - 672

EP - 675

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

IS - Pt 8

ER -

Synthesis and structure of 6-bromo-2-(diethoxy-methyl)-2-hydroxy-3-phenyl-2,3-dihydro-1Himidazo[1,2-a]pyridin-4-ium chloride acetonitrile monosolvate

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Keywords

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