2-Chloro-4-hydroxyanilinium chloride

The title compound, C<sub>6</sub>H<sub>7</sub>ClNO<sup>+</sup>·Cl<sup>-</sup>, crystallizes in ortho-rhom-bic space group <i>Pnma</i> with both cations and anions lying on a mirror plane in the crystal. The C-Cl distance is 1.7289 (6) Å, the C-N distance is 1.4590 (8) Å, and the C-O distance is 1.3617 (8) Å. Parallel mol-ecules form stacks with inter-planar spacing 3.1473 (2) Å, but slipped by 1.97 Å. The NH<sub>3</sub> <sup>+</sup> substituent donates three inter-molecular hydrogen bonds to chloride ions having N⋯Cl distances in the range 3.1514 (6)-3.3019 (2) Å, and the OH group donates an inter-molecular hydrogen bond to chloride with O⋯Cl distance 3.0671 (6) Å. The chloro substituent and OH group do not accept hydrogen bonds from NH or OH.

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IUCrData
Published
2025-10-17
DOI
https://doi.org/10.1107/s2414314625008934
Primary Topic
Synthesis and Reactions of Organic Compounds
Type
article
Field-Weighted Citation Impact
0.00

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article

2-Chloro-4-hydroxyanilinium chloride

Rao M. Uppu, Sagala Bai, Patrick Mensah, Frank Rolf Fronczek et al.
IUCrData
Synthesis and Reactions of Organic Compounds
article

2-Chloro-4-hydroxyanilinium chloride

Rao M. Uppu, Sagala Bai, Patrick Mensah, Frank Rolf Fronczek, Guoqiang Li
article en

Abstract

The title compound, C<sub>6</sub>H<sub>7</sub>ClNO<sup>+</sup>·Cl<sup>-</sup>, crystallizes in ortho-rhom-bic space group <i>Pnma</i> with both cations and anions lying on a mirror plane in the crystal. The C-Cl distance is 1.7289 (6) Å, the C-N distance is 1.4590 (8) Å, and the C-O distance is 1.3617 (8) Å. Parallel mol-ecules form stacks with inter-planar spacing 3.1473 (2) Å, but slipped by 1.97 Å. The NH<sub>3</sub> <sup>+</sup> substituent donates three inter-molecular hydrogen bonds to chloride ions having N⋯Cl distances in the range 3.1514 (6)-3.3019 (2) Å, and the OH group donates an inter-molecular hydrogen bond to chloride with O⋯Cl distance 3.0671 (6) Å. The chloro substituent and OH group do not accept hydrogen bonds from NH or OH.

IUCrDataVol. 10(10)
Louisiana State University (US), Southern University and Agricultural and Mechanical College (US)
National Science Foundation, National Institutes of Health, National Institute of General Medical Sciences, Division of Chemistry
Openalex Percentile: Top 77%
Synthesis and Reactions of Organic Compounds
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