N-(3,4-Difluoro­phen­yl)-3,4,5-trimethoxy­benzamide

Choi, H.; Han, B.H.; Lee, T.; Kang, S.K.; Sung, C.K.

doi:10.1107/S1600536810013796

Volume 66
Part 5
Page o1142
May 2010

Received 13 April 2010
Accepted 14 April 2010
Online 24 April 2010

Key indicators
Single-crystal X-ray study
T = 174 K
Mean (C-C) = 0.006 Å
R = 0.065
wR = 0.185
Data-to-parameter ratio = 12.2
Details

N-(3,4-Difluorophenyl)-3,4,5-trimethoxybenzamide

Hyeong Choi,^a Byung Hee Han,^a Taewoo Lee,^a Sung Kwon Kang ^a ^* and Chang Keun Sung ^b

^aDepartment of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea, and ^bDepartment of Food Science and Technology, Chungnam National University, Daejeon 305-764, Republic of Korea
Correspondence e-mail: skkang@cnu.ac.kr

In the title amide, C₁₆H₁₅F₂NO₄, the dihedral angle between the benzene rings is 2.33 (15)°. Molecules are linked in the crystal structure by N-HO hydrogen bonding involving N-H and C=O groups of the amide function, leading to a supramolecular chain along [100].

Related literature

For background to the development of potent inhibitory agents of tyrosinase and melanin formation as whitening agents, see: Cabanes et al. (1994); Dawley & Flurkey (1993); Ha et al. (2007); Hong et al. (2008); Kwak et al. (2010); Lee et al. (2007); Nerya et al. (2003); Park et al. (2010); Sung & Samyang Genex (2001); Yi et al. (2009, 2010).

Experimental

Crystal data

C₁₆H₁₅F₂NO₄
M_r = 323.29
Monoclinic, P 2₁ /n
a = 5.0031 (3) Å
b = 8.8986 (5) Å
c = 32.726 (2) Å
= 93.896 (4)°
V = 1453.59 (15) Å³
Z = 4
Mo K radiation
= 0.12 mm^-1
T = 174 K
0.12 × 0.05 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer
10828 measured reflections
2634 independent reflections
1522 reflections with I > 2(I)
R_int = 0.080

Refinement

R[F² > 2(F²)] = 0.065
wR(F²) = 0.185
S = 1.05
2634 reflections
216 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.32 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N15-H15O14ⁱ	0.93 (4)	2.02 (4)	2.872 (4)	152 (3)
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2658 ).

Acknowledgements

We wish to thank the DBIO company for partial support of this work.

References

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organic compounds