N-(4-Hy­droxy­phen­yl)-4-nitro­benzamide

Ghulam Waris; Humaira Masood Siddiqi; Ulrich Flörke; Shaukat Saeed; M Saeed Butt

doi:10.1107/S1600536813006132

. 2013 Mar 9;69(Pt 4):o526. doi: 10.1107/S1600536813006132

N-(4-Hydroxyphenyl)-4-nitrobenzamide

Ghulam Waris ^a, Humaira Masood Siddiqi ^a,^*, Ulrich Flörke ^b, Shaukat Saeed ^c, M Saeed Butt ^a

PMCID: PMC3629581 PMID: 23634068

Abstract

The molecular structure of the title compound, C₁₃H₁₀N₂O₄, shows an almost planar conformation as the benzene rings make a dihedral angle of 2.31 (7)°. The nitro group lies in plane with the benzamide ring, with a C—C—N—O torsion angle of 0.6 (2)°. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds link molecules into sheets stacked along [10-1].

Related literature

For background to aromatic polyimides, see: Sheng et al. (2009 ▶). For the solubilizing role of ether and amide groups in polyimides, see: Litvinov et al. (2010 ▶). For a related structure, see: Raza et al. (2010 ▶). graphic file with name e-69-0o526-scheme1.jpg

Experimental

Crystal data

C₁₃H₁₀N₂O₄
M _r = 258.23
Monoclinic,
a = 7.5187 (5) Å
b = 12.5695 (9) Å
c = 11.7932 (8) Å
β = 90.033 (2)°
V = 1114.53 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 130 K
0.50 × 0.16 × 0.12 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.944, T _max = 0.986
10323 measured reflections
2657 independent reflections
2255 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.122
S = 1.12
2657 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supplementary Material

Click here for additional data file.^{(16.6KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813006132/tk5203sup1.cif

e-69-0o526-sup1.cif^{(16.6KB, cif)}

Click here for additional data file.^{(130.5KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006132/tk5203Isup2.hkl

e-69-0o526-Isup2.hkl^{(130.5KB, hkl)}

Click here for additional data file.^{(4.6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813006132/tk5203Isup3.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
O4—H4⋯O1ⁱ	0.84	1.94	2.7803 (17)	175
N1—H1A⋯O3ⁱⁱ	0.88	2.33	3.1664 (18)	159

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

Acknowledgments

The contribution to this project of the Higher Education Commission of Pakistan by providing financial assistance through the International Research Support Initiative Programme (IRSIP) is acknowledged by the authors.

supplementary crystallographic information

Comment

Fairly high thermooxidative and outstanding thermal stability, exceptional mechanical and electrical properties and upright chemical resistance are some distinctions of aromatic polyimides that make them documented as high performance polymeric materials (Sheng et al., 2009). The reported title compound, (I), containing ether and amide groups, serve multiple purposes, such as a boost in solubility and upsurge thermal stability of the resulting polyimide (Litvinov et al., 2010). In this connection, the title compound was investigated.

The molecular structure of (I), Fig. 1, is approximately planar with the dihedral angle between the two benzene rings being 2.31 (7)°. Intermolecular N—H···O and O—H···O hydrogen bonds, Table 1, link molecules into sheets stacked approximately along [1 0 1], Fig. 2. The structure of the isomeric 2-hydroxy-N-(3-nitrophenyl)benzamide compound is known (Raza et al., 2010).

Experimental

Reagent grade quality chemicals were used in this preparation. 4-Aminophenol (0.94 g, 8.6 mmol) in dry dichloromethane (30 ml), a few drops of N, N-dimethylformamide (DMF) and triethylamine (1.25 ml, 8.6 mmol) were placed in a 100 ml, three necked, round bottomed flask, equipped with a condenser, a nitrogen gas inlet tube, a thermometer and a magnetic stirrer. The mixture was stirred at 273–278 K for 30–45 minutes. A solution of 4-nitrobenzoyl chloride (1.59 g, 8.6 mmol) in dichloromethane (20 ml) was added drop-wise via a dropping funnel along with continuous stirring. The reaction mixture was then refluxed for 45 minutes. The flask contents were cooled to room temperature, poured into water and let to stand for 24 h. The resulting bright-yellow precipitate was filtered, washed with hot water and 5% NaOH solution. Finally, product was washed with hot water and dried under vacuum at 350 K. The crude product was recrystallized from ethanol and dichloromethane (2:1, v/v). Yield: 91%; m.p. 406–407 K.