Methyl 2,4-dihy­droxy-5-(2-methyl­propanamido)­benzoate

Syeda Sohaila Naz; Nazar Ul Islam; M Nawaz Tahir; Muhammad Raza Shah

doi:10.1107/S1600536813000457

. 2013 Jan 12;69(Pt 2):o221. doi: 10.1107/S1600536813000457

Methyl 2,4-dihydroxy-5-(2-methylpropanamido)benzoate

Syeda Sohaila Naz ^a, Nazar Ul Islam ^a, M Nawaz Tahir ^b,^*, Muhammad Raza Shah ^c

PMCID: PMC3569756 PMID: 23424502

Abstract

In the title compound, C₁₂H₁₅NO₅, the dihedral angle between the benzene ring and the C atoms of the terminal isopropyl group is 83.48 (16)°. Intramolecular N—H⋯O and O—H⋯O hydrogen bonds generate S(5) and S(6) rings, respectively. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, generating C(7) chains propagating in [001]. Weak aromatic π–π stacking [centroid–centroid separation = 3.604 (3) Å] is also observed.

Related literature

For related structures, see: Chen et al. (2011 ▶); Naz et al. (2013 ▶).

Experimental

Crystal data

C₁₂H₁₅NO₅
M _r = 253.25
Monoclinic,
a = 22.732 (4) Å
b = 8.2338 (16) Å
c = 14.743 (3) Å
β = 113.506 (9)°
V = 2530.4 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.26 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.981, T _max = 0.985
8480 measured reflections
2218 independent reflections
950 reflections with I > 2σ(I)
R _int = 0.090

Refinement

R[F ² > 2σ(F ²)] = 0.065
wR(F ²) = 0.168
S = 0.96
2218 reflections
169 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.19 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 (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON.

Supplementary Material

Click here for additional data file.^{(22KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813000457/hb7024sup1.cif

e-69-0o221-sup1.cif^{(22KB, cif)}

Click here for additional data file.^{(106.9KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000457/hb7024Isup2.hkl

e-69-0o221-Isup2.hkl^{(106.9KB, hkl)}

Click here for additional data file.^{(5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813000457/hb7024Isup3.cml

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
N1—H1⋯O4	0.86	2.19	2.604 (4)	109
O3—H3⋯O2	0.82	1.87	2.595 (4)	146
O4—H4⋯O5ⁱ	0.82	1.820	2.633 (4)	174

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the provision of funds for the purchase of a 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 biological studies in continuation to form different derivatives of methyl 5-amino-2,4-dihydroxybenzoate (Naz et al., 2013). The crystal structure of 3-hydroxy-2-(isobutyrylamino)benzamide (Chen et al., 2011) has been published which is related to the title compound.

In (I), the groups A (C1—C8/O1—O4/N1) of methyl 5-amino-2,4-dihydroxybenzoate is almost planar with r. m. s. deviation of 0.0190 Å. The C9 and O5 atoms are at a distance of -0.1205 (50) and -0.3867 (44) Å from the mean square plane of the group A. The isopropyl group B (C10—C12) is of course planar. The dihedral angle between A/B is 83.24 (15)°. There exist strong intramolecular H-bondings of N—H···O and O—H···O types (Table 1, Fig. 2) completing S(5) and S(6) ring motifs. There also exist strong intermolecular H-bondings of O—H···O type due to which C(7) chains are formed (Table 1, Fig. 2) resulting in the formation of one dimensional polymeric network along the c-axis. There also exist π–π interactions between the centroids of benzene rings at a distance of 3.604 (3) Å.

Experimental

Equivalent amounts of methyl 5-amino-2,4-dihydroxybenzoate (0.2 g, 1.1 mmol) and Isobutyric anhydride (0.2 ml, 1.1 mmol) were heated at 333 K for 3 h in dimethylformamide (DMF). The reaction mixture was kept for 48 h to afford brown needles of the title compound.