5-Carb­oxy-2,4-dihy­droxy­anilinium chloride

Syeda Sohaila Naz; Nazar Ul Islam; M Nawaz Tahir

doi:10.1107/S1600536810033337

. 2010 Aug 21;66(Pt 9):o2372. doi: 10.1107/S1600536810033337

5-Carboxy-2,4-dihydroxyanilinium chloride

Syeda Sohaila Naz ^a, Nazar Ul Islam ^a, M Nawaz Tahir ^b,^*

PMCID: PMC3007849 PMID: 21588711

Abstract

In the title salt, C₇H₈NO₄ ⁺·Cl⁻, the organic group is planar with an r.m.s. deviation of 0.0265 Å. An S(6) ring motif is formed due to an intramolecular O—H⋯O hydrogen bond. The compound consists of dimers due to intermolecular O—H⋯O hydrogen bonds with an R ₂ ²(8) ring motif. The dimers are interlinked through strong N—H⋯Cl and O—H⋯Cl hydrogen bonds, resulting in a three-dimensional polymeric network.

Related literature

For related structures, see: Bendjeddou et al. (2009 ▶); Dobson & Gerkin (1998 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₇H₈NO₄ ⁺·Cl⁻
M _r = 205.59
Monoclinic,
a = 5.0667 (3) Å
b = 28.4071 (13) Å
c = 6.3966 (3) Å
β = 97.649 (3)°
V = 912.47 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 296 K
0.28 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.926, T _max = 0.935
7094 measured reflections
1635 independent reflections
1108 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.098
S = 1.01
1635 reflections
128 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033337/si2289sup1.cif

e-66-o2372-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033337/si2289Isup2.hkl

e-66-o2372-Isup2.hkl^{(78.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.85 (3)	1.81 (3)	2.653 (3)	177 (4)
N1—H1A⋯Cl1ⁱⁱ	0.89	2.24	3.124 (3)	176
N1—H1B⋯Cl1ⁱⁱⁱ	0.89	2.29	3.176 (3)	173
N1—H1C⋯Cl1^iv	0.89	2.35	3.217 (2)	163
O3—H3⋯O2	0.85 (4)	1.84 (3)	2.632 (3)	154 (3)
O4—H4A⋯Cl1^v	0.85 (3)	2.15 (3)	2.985 (2)	170 (3)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

supplementary crystallographic information

Comment

The title compound (I, Fig. 1) has been prepared for derivatization and for the synthesis of metallic complexes.

The crystal structure of (II) i.e., 5-ammoniosalicylic Acid chloride monohydrate (Dobson & Gerkin, 1998) and (III) i.e., bis(3-carboxyanilinum) bis(perchlorate) monohydrate (Bendjeddou et al., 2009) have been published which are related to the title compound.

In (I), the organic group (C1—C7/O1—O4/N1) is planar with r. m. s. deviation of 0.0265 Å. There exist a strong intramolecular H-bond of O—H···O type (Table 1, Fig. 1) completing an S(6) ring motif (Bernstein et al., 1995) in the organic part. The title compound consists of dimers due to intermolecular H-bond of O—H···O type (Table 1, Fig. 2) completing R₂²(8) ring motif. The dimers are interlinked through strong H-bondings of N—H···Cl and O—H···Cl types (Table 1, Fig. 2) resulting in a three dimensional polymeric network.

Experimental

Concentrated nitric acid (2 mL, 67%) was added drop by drop to β-resorcylic acid (1 g, 97%, 6.3 mmol) in a round bottom flask. The mixture was protected from moisture by CaCl₂ (anhydrous) tube and was allowed to stand for 12 h at room temperature. Then the reaction mixture was diluted with water. The crude material was filtered and recrystallized from water to affoard the 5-nitro-β-resorcylic acid.

Then a mixture of 5-nitro-β-resorcylic acid (1.5 g, 7.5 mmol), tin (3 g, 25 mmol), concentrated hydrochloric acid (8 ml, 37%) and absolute ethanol (5 ml) were taken in a 100 ml round bottom flask and heated under reflux with stirring for 40 min. The completion of the reaction was monitored by TLC. The reaction mixture was filtered to remove any unreacted tin. The filtrate was kept for seven days to afford light green prisms of (I).