Citation: HE Dian, YANG Zhu-Qing, HOU Meng. Synthesis and Crystal Structure of 4-Chloro-N- (2-(2-nitrophenyl)acetoxy)-N-(m-tolyl)benzamide[J]. Chinese Journal of Structural Chemistry, ;2014, 33(9): 1388-1394. shu

Synthesis and Crystal Structure of 4-Chloro-N- (2-(2-nitrophenyl)acetoxy)-N-(m-tolyl)benzamide

HE Dian ^a,b,, ,
YANG Zhu-Qing ^a ,
HOU Meng ^a

1.
a Institute of Medicinal Chemistry, School of Pharmaceutical Science, Lanzhou University, Lanzhou 730000, China;
2.
b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China

Corresponding author: HE Dian,
Received Date: 24 February 2014
Available Online: 28 May 2014
Fund Project: Supported by the Fundamental Research Funds for the Central Universities (lzujbky-2010-137) (lzujbky-2010-137)

The new title compound 4-chloro-N-(2-(2-nitrophenyl)acetoxy)-N-(m-tolyl)benzamide (C₂₂H₁₇ClN₂O₅, M_r=424.82) has been synthesized via the reaction of 4-chloro-N-hydroxy-N-(m-tolyl)benzamide with 2-(2-nitrophenyl)acetyl chloride. The structure of the product was confirmed by ¹H NMR, ¹³C NMR, IR, HRMS (ESI) and single-crystal X-ray diffraction. The title compound crystallizes in the monoclinic system, space group P2₁/c with a=13.0269(10), b=6.7251(6), c=23.9313(16) Å, β=99.931(6)°, V=2065.1(3) Å³, Z=4, Dc=1.366 g/cm³, F(000)=880, μ=0.221 mm^-1, the final R=0.0600 and wR=0.1754 for 1981 observed reflections (I > 2σ(I)). X-ray analysis indicates that the chloro-phenyl ring (C(10)~C(15)) and the methyl-substituted benzene ring (C(16)~C(21)) are not coplanar with the nitro-substituted benzene ring (C(1)~C(6)), with the dihedral angle to be 70.78° and 63.72°, respectively. Hydrogen bonds C(2)-H(2)…O(2) and C(7)-H(7B)…O(5) are observed.
- crystal structure,
- synthesis,
- 4-chloroN-(2-(2-nitrophenyl)acetoxy)-N-(m-tolyl) benzamide
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