Asian Journal of Chemistry; Vol. 25, No. 11 (2013), 6186-6188
Supramolecular Structure of 2,4,6-Trinitrophenol
*
YIN-XIA SUN , ZONG-LI REN and WEI-SHENG MENG
School of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, P.R. China
*Corresponding author: E-mail: sun_yinxia@163.com
(Received: 13 July 2012;
Accepted: 2 May 2013)
AJC-13431
The compound 2,4,6-trinitrophenol with the molecular formula C6H3N3O7, crystallizes with two crystallographically independent but
chemically identical molecules in the asymmetric unit. The dihedral angle formed by the two benzene rings is about 67.49º. The crystal
structure displays four intramolecular hydrogen bonds between the hydrogen atoms from the phenolic alcohols and the oxygen or nitrogen
atoms from the nitro groups. In the crystal structure, the intermolecular O-H···O and C-H···O hydrogen bonding interactions link molecules
into infinite three-dimensional supramolecular network structure.
Key Words: 2,4,6-Trinitrophenol, Supramolecular structure.
C, 31.45; H, 1.32; N, 18.34. Found (%): C, 31.32; H, 1.34; N,
18.27.
INTRODUCTION
Nitro compounds, especially aromatic nitro compounds
have been widely studied owing to their potential application
in, for example, pathology1, materials science2 and nonlinear
optical (NLO) materials3. 2,4,6-Trinitrophenol, commonly
known as picric acid (TNP), is a nonlinear optical crystal with
molecular formula C6H3N3O7. 2,4,6-Trinitrophenol is also a
well-known material used in dyeing industry4. Herein, we
report the supramolecular structure of 2,4,6-trinitrophenol.
TABLE-1
CRYSTAL DATA AND REFINEMENT
PARAMETERS FOR THE TITLE COMPOUND
Empirical formula
Formula weight
Temperature
C6H3N3O7
229.11
298(2) K
Wavelength
0.71073 Å
Crystal system
Space group
Orthorhombic
Pca2(1)
Cell dimensions
a = 9.2596(12) Å, b = 19.138(2) Å, c =
EXPERIMENTAL
9.7075(14) Å, α = 90º, β = 90º, γ = 90º
1720.3(4) Å3
The reagents and solvents were analytical grade reagents
used without further purification. C, H and N analyses were
carried out with a GmbHVariuoELV3.00 automatic elemental
analyzer. X-Ray single crystal structure was determined on a
Bruker Smart APEX CCD area detector. Melting points was
measured by the use of a microscopic melting point apparatus
made in Beijing Taike Instrument Limited Company and the
thermometer was uncorrected.
General procedure: To an acetone solution (30 mL) of
2,2'-[ethylenedioxybis(nitriloethylidyne)]diphenol (54.0 mg,
0.164 mmol) was added an acetone solution (20 mL) of copper
picrate tetrahydrate (96.0 mg, 0.162 mmol). The colour of the
mixed solution turned to brilliant yellow immediately. Then
the mixture was placed in a hexane atmosphere, after 2 months,
several yellow primatical crystals of the title compound suitable
for X-ray diffraction analysis were obtained unexpectedly.
Yield, 25.9 %. m.p. 401-402 K.Anal. calcd. (%) for C6H3N3O7:
Volume
Z
Density (calculated)
Absorption coefficient
F(000)
8
1.769 mg/m3
0.166 mm-1
928
Index ranges
-10 ≤ h ≤ 11, -14 ≤ k ≤ 22, -11 ≤ l ≤ 11
Reflections collected/unique 7969 / 3008 [R(int) = 0.0420]
Data/restraints/parameters
Goodness of fit indicator
R [I > 2σ(I)]
3008 / 1 / 289
1.027
R1 = 0.0532, wR2 = 0.1355
0.463 and -0.221 e Å-3
Largest diff. peak and hole
X-Ray structure determination: The single crystal of
the 2,4,6-trinitrophenol, with approximate dimensions of 0.38
mm × 0.27 mm × 0.12 mm was placed on a Bruker Smart
1000 diffractmeter equipped with Apex CCD area detector.
The diffraction data were collected using a graphite
monochromated MoKα radition (λ = 0.71073 Å) at 298(2) K.