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

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

doi:10.1107/S160053681300024X

. 2013 Jan 9;69(Pt 2):o207. doi: 10.1107/S160053681300024X

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

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

PMCID: PMC3569267 PMID: 23424490

Abstract

In the title compound, C₁₅H₁₂N₂O₇, the dihedral angle between the aromatic rings is 4.58 (13)° and the nitro group is rotated from its attached ring by 18.07 (17)°. 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 [001] C(7) chains. The chains are linked by C—H⋯O interactions, forming a three-dimensional network, which incorporates R ₂ ²(7) and R ₂ ²(10) loops.

Related literature

For a related structure, see: Gorelik et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₅H₁₂N₂O₇
M _r = 332.27
Monoclinic,
a = 30.412 (6) Å
b = 6.9325 (15) Å
c = 14.936 (3) Å
β = 111.737 (8)°
V = 2925.0 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.12 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, 2009 ▶) T _min = 0.970, T _max = 0.980
10681 measured reflections
2885 independent reflections
1519 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.134
S = 0.98
2885 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.24 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.^{(24KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681300024X/hb7022sup1.cif

e-69-0o207-sup1.cif^{(24KB, cif)}

Click here for additional data file.^{(138.8KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300024X/hb7022Isup2.hkl

e-69-0o207-Isup2.hkl^{(138.8KB, hkl)}

Click here for additional data file.^{(5.8KB, cml)}

Supplementary material file. DOI: 10.1107/S160053681300024X/hb7022Isup3.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	2.16	2.595 (3)	111
O3—H3A⋯O2	0.82	1.91	2.619 (3)	144
O4—H4⋯O5ⁱ	0.82	1.86	2.670 (2)	170
C8—H8A⋯O3ⁱⁱ	0.96	2.51	3.274 (4)	137
C12—H12⋯O7ⁱⁱⁱ	0.93	2.38	3.297 (4)	171
C15—H15⋯O4ⁱⁱ	0.93	2.46	3.370 (3)	165

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

Acknowledgments

The authors acknowledge the provision of funds for the purchase of the 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 biological studies. The crystal structure of 4-((4-nitrobenzoyl)amino)benzoic acid (Gorelik et al., 2010) 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 and B (C9—C15/O5—O7/N2) of 4-nitrobenzoyl are planar with r. m. s. deviation of 0.0252 and 0.0363 Å, respectively. The dihedral angle between A/B is 3.59 (3)°. 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 (Bernstein et al., 1995). There also exist strong intermolecular H-bondings of C—H···O and O—H···O types due to which R₂²(7) and R₂²(10) loops are formed (Table 1, Fig. 2) resulting in the formation of three dimensional polymeric network.

Experimental

Equivalent amounts of methyl 5-amino-2,4-dihydroxybenzoate (0.20 g, 1.1 mmol) and 4-nitrobenzoyl chloride (0.20 g, 1.1 mmol) were heated at 333 K for 3 h in dimethylformamide (DMF). The reaction mixture was freeze dried, neutralized with aq. NaHCO₃ (5%) and extracted with dichloromethane (DCM), dried over Na₂SO₄ and evaporated in vacuo to give pure product which was recrystallized from methanol and water solution to afford yellow needles.