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International Journal of ChemTech Research CODEN (USA): IJCRGG ISSN: 0974-4290 Vol.9, No.04 pp 301-305, 2016
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Crystal structure analysis of N,2-diphenylacetamide
K. Elumalai1, Subramaniyan Sathiyaraj2, B. Mohamad Ali2,
A. Sultan Nasar2, K. Sakthi Murugesan1*
1,1*Department of Physics, Presidency College (Autonomous), Chennai-600 005, India
2Department of PolymerScience, University of Madras, Guindy campus,
Chennai 602 025, India
Abstract: The crystal structure ofN,2-diphenylacetamide(C28H26N2O2). The compound crystallizes in OrthorhombicPna21space group with unit cell parameters at 296(2) K as follows: a = 9.1034(5) Å, b =10.552(6) Å, c =11.769(8) Å, α = β = γ = 90°.Crystal data were collected using BRUKER SMART APEX II CCD X-ray diffractometer. The structure was solved by direct methods and refined on F2 by full-matrix least-squares procedures to the final R1 of 0.060 using SHELXL programs.
Key Words: acetamide and crystal structure.
Introduction
Schiff base compounds are some of the most important stereochemical models in transition metal coordination chemistry,with their ease of preparation and structural variations1. In continuation of our works on the synthesisand structural characterization of Schiff base ligands here we report the structure of the title compound.
Experimental
X-ray Structure Determination
Single crystal of the compound suitable for x-ray diffraction was obtained by slow evaporationmethod. Three dimensional intensity data were collected on a Bruker2 SMART APEX CCD Diffractometer using graphite monochromatized Mo-Kα radiation (λ= 0.71073 Å) at Department of chemistry, IIT, Chennai, India. The structure was solved by direct methods and refined on F2 by full-matrix least-squares procedures using the SHELXL programs3. All the non-hydrogen atoms were refined using isotropic and later anisotropic thermal parameters. The hydrogen atoms were included in the structure factor calculation at idealized positions by using a riding model, but not refined. Images were created with ORTEP-34.The crystallographic data for the compound are listed in Table 1.
Table 1: Crystal data and structure refinement of the titled compound
Compound |
Parameters |
Empirical formula |
C28 H26 N2 O2 |
Formula weight |
422.51 |
Temperature |
293(2) K |
Wavelength |
0.71073 Å |
Crystal system, space group |
Pna21, Orthorhombic |
Unit cell dimensions |
a = 9.1034(5) Å alpha = 90° |
|
b = 10.5529(6) Å beta = 90° |
|
c = 11.7699(8) Å gamma = 90° |
Volume |
1130.70(12) Å3 |
Z, Calculated density |
2, 1.241 Mg/m3 |
Absorption coefficient |
0.078 mm-1 |
F(000) |
448 |
Crystal size |
0.25 x 0.16 x 0.10 mm |
Theta range for data collection |
2.59 to 24.99 deg. |
Limiting indices |
-10<=h<=8, -12<=k<=12, -13<=l<=8 |
Reflections collected / unique |
4641 / 1507 [R(int) = 0.0204] |
Completeness to theta = 24.99 |
99.90% |
Refinement method |
Full-matrix least-squares on F2 |
Data / restraints / parameters |
1507 / 1 / 145 |
Goodness-of-fit on F2 |
1.083 |
Final R indices [I>2sigma(I)] |
R1 = 0.0609, wR2 = 0.1505 |
R indices (all data) |
R1 = 0.0626, wR2 = 0.1541 |
Largest diff. peak and hole |
0.322 and -0.477 e.Å-3 |
Synthesis of the compound
To a solution of 2-phenylacetic acid (1.0 mmol) in toluene (6 mL) 20 mol% FeCl3 and an additional0.5 eq. of AcOH were added and the reaction mixture was stirred at 50oC for 10–15 min. Then an aniline (1.0 mmol)in toluene (4 mL) was added slowly to the above reaction mixture. The reaction mixture was refluxed at 75oC and the reaction was completed overnight monitored by TLC. Upon complete consumption of the starting materials, the reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The crude product was extracted into EtOAc (15 mL). The EtOAc layer was then washed with 5% Na2CO3 (5 mL), dil. HCl (5 mL), water (2 X5 mL) and brine (5 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was evaporated in vacuum to afford the crude which was then purified through silica gel column chromatography (EtOAc/hexane). Then the product was dissolved in EtoAc and do warm-up and kept in RT, finally we got yellow colored crystal. The scheme diagram is given below.
Results and Discussion
The Asymmetric unit of the title compound is shown in Fig. 1. The two phenyl rings are essentially coplanar,making a dihedral angle of 23.14°.The carbamate group is twisted slightly from the attached benzene ring, with a C—N—C—O torsion angle of 1.1(5)°.
In the crystal, molecules are linked by pairs of N---H...O hydrogen bonds, forming inversion dimers with an R22(6) ring motif. The dimers are linked by pairs of C---H...O hydrogen bonds, enclosing R22(6) ring motif, forming chains along [010](Fig 2& Table 2). The crystal packing is further stabilized by C---H...㕅and 㕅---㕅intermolecular interactions.The selected bond lengths and angles are listed in table 3 and 4, respectively.
Table 2: Hydrogen-bond geometry [Å]
Symmetry code: i) -1/2+x,1/2-y,z
Distance (Å) |
Angle (º) |
|||
D—H…A |
D—H |
H…A |
D…A |
D—H…A |
N1---H1A…O1i |
0.86 |
1.98 |
2.799(3) |
160 |
C8---H8A…O1ii |
0.97 |
2.59 |
2.922(3) |
100 |
C8---H8B…O1iii |
0.97 |
2.44 |
2.922(3) |
111 |
Fig.1.The molecular structure of the title compound, with the atom-numbering scheme. The displacement ellipsoids are drawn at 30% probability level. H atoms are shown as spheres of arbitrary radius.
Fig.2. The crystal packing of the title compound, viewed along b axis, showing N---H...O and C---H…O hydrogen bonds.The hydrogen bonds are shown as dashed lines(see Table 2 for details).
Table 3: Selected Bond lengths (Å)Table 4: Selected Bond angles (º)
Bond |
Length (Å) |
C(1)-C(6) |
1.369(5) |
C(1)-C(2) |
1.394(6) |
C(1)-H(1) |
0.93 |
C(2)-C(3) |
1.377(7) |
C(2)-H(2) |
0.93 |
C(3)-C(4) |
1.363(7) |
C(3)-H(3) |
0.93 |
C(4)-C(5) |
1.399(5) |
C(4)-H(4) |
0.93 |
C(5)-C(6) |
1.381(5) |
C(5)-H(5) |
0.93 |
C(6)-N(1) |
1.419(4) |
C(7)-O(1) |
1.224(3) |
C(7)-N(1) |
1.337(4) |
C(7)-C(8) |
1.371(4) |
C(8)-C(9) |
1.417(4) |
C(8)-H(8A) |
0.97 |
C(8)-H(8B) |
0.97 |
C(9)-C(14) |
1.376(5) |
C(9)-C(10) |
1.386(4) |
C(10)-C(11) |
1.373(5) |
C(10)-H(10) |
0.93 |
C(11)-C(12) |
1.354(5) |
C(11)-H(11) |
0.93 |
C(12)-C(13) |
1.381(6) |
C(12)-H(12) |
0.93 |
C(13)-C(14) |
1.371(6) |
C(13)-H(13) |
0.93 |
C(14)-H(14) |
0.93 |
N(1)-H(1A) |
0.86 |
Bond |
Angle ( º) |
C(6)-C(1)-C(2) |
119.7(4) |
C(6)-C(1)-H(1) |
120.1 |
C(2)-C(1)-H(1) |
120.1 |
C(3)-C(2)-C(1) |
120.3(4) |
C(3)-C(2)-H(2) |
119.9 |
C(1)-C(2)-H(2) |
119.9 |
C(4)-C(3)-C(2) |
119.8(4) |
C(4)-C(3)-H(3) |
120.1 |
C(2)-C(3)-H(3) |
120.1 |
C(3)-C(4)-C(5) |
120.5(4) |
C(3)-C(4)-H(4) |
119.8 |
C(5)-C(4)-H(4) |
119.8 |
C(6)-C(5)-C(4) |
119.3(3) |
C(6)-C(5)-H(5) |
120.3 |
C(4)-C(5)-H(5) |
120.3 |
C(1)-C(6)-C(5) |
120.3(3) |
C(1)-C(6)-N(1) |
118.5(3) |
C(5)-C(6)-N(1) |
121.1(3) |
O(1)-C(7)-N(1) |
124.3(3) |
O(1)-C(7)-C(8) |
121.8(3) |
N(1)-C(7)-C(8) |
113.9(2) |
C(7)-C(8)-C(9) |
125.2(2) |
C(7)-C(8)-H(8A) |
106 |
C(9)-C(8)-H(8A) |
106 |
C(7)-C(8)-H(8B) |
106 |
C(9)-C(8)-H(8B) |
106 |
H(8A)-C(8)-H(8B) |
106.3 |
C(14)-C(9)-C(10) |
119.5(3) |
Conclusion
The crystal structure analysis of a novel N,2-diphenylacetamidecompound was studied using x-ray diffraction method. In the crystal, molecules are linked by pairs of N---H...O hydrogen bonds, forming inversion dimers with an R22(6) ring motif. The dimers are linked by pairs of C---H...O hydrogen bonds, enclosing R22(6) ring motif, forming chains along [010]
Acknowledgments
The authors thank the Department of chemistry, IIT, Chennai, India, for X-ray intensity data collection.
References
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