Citation: LIU Xiao-Feng, ZHANG Yang, LI Jing, ZHAO Jing-Si, XI Na, HE Dian. Synthesis and Crystal Structure of N-((3-(2-nitrophenyl) propanoyl)oxy)-N-phenylbenzamide[J]. Chinese Journal of Structural Chemistry, ;2015, 34(5): 688-694. doi: 10.14102/j.cnki.0254-5861.2011-0615 shu

Synthesis and Crystal Structure of N-((3-(2-nitrophenyl) propanoyl)oxy)-N-phenylbenzamide

LIU Xiao-Feng ^a ,
ZHANG Yang ^b,c ,
LI Jing ^b,c ,
ZHAO Jing-Si ^b,c ,
XI Na ^b,c ,
HE Dian ^b,,

1.
a School of Life Science and Engineering, Lanzhou University of Technology, Lanzhou 730050, China;
2.
b Institute of Medicinal Chemistry, School of Pharmaceutical Science, Lanzhou University, Lanzhou 730000, China;
c Lanzhou Way Biological Science and Technology Development Co.
c Lanzhou Way Biological Science and Technology Development Co., LTD

Corresponding author: HE Dian,
Received Date: 25 December 2014
Available Online: 2 February 2015
Fund Project:

The title compound N-((3-(2-nitrophenyl) propanoyl)oxy)-N-phenylbenzamide (C₂₂H₁₈N₂O₅, M_r=390.38) was synthesized with nitrobenzene as the starting materials and structurally characterized by ¹H NMR, ¹³C NMR, IR, H RMS(E-SI) and single-crystal X-ray diffraction. The crystalline structure of the title compound was studied in detail. The single-crystal X-ray diffraction revealed that the compound crystallizes in monoclinic, space group P2₁/n, with a=14.4481(7), b=8.0089(5), c=16.6808(9) Å, α=90.00(5), β=100.069(5), γ=90.00(5)°, M_r=390.38, V=1900.46(18) Å³, Z=4, D_c=1.364 g/cm^-3, μ=0.098, F(000)=816.0, the final R=0.0530 and wR=0.1141 for 2525 observed reflections (I>2σ(I)), R(all data)=0.0813, wR(all data)=0.1335, completeness to theta of 26.020 is 99.8% and GOF=1.085. The crystal structure contains three branched chains with its center placed at the midpoint of N. The phenyl ring (C(8)~C(13)) makes a dihedral angle of 83.5(1)℃ with the phenyl ring (C(1)~C(6)), and 80.5(1)℃ with the nitro-substituted benzene ring (C(17)~C(22)), indicating that the three rings are not coplanar. Hydrogen bonds (C(10)-H(10)···O(3)), (C(15)-H(15B)···O(4) and C(16)-H(16B)···O(4)) together with π-π stacking interactions stabilize the structure of the molecule. The preliminary biological test shows that the title compound has good antitumor activity against A549 in vitro with the IC50 value of 3.17 μmol.
- crystal structure,
- synthesis,
- N-((3-(2-nitrophenyl) propanoyl) oxy)-N-phenylbenzamide
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