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Volume 69 
Part 10 
Page o1596  
October 2013  

Received 8 July 2013
Accepted 24 September 2013
Online 28 September 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.050
wR = 0.132
Data-to-parameter ratio = 14.2
Details
Open access

4'-Acetyl-3''-carbamoyl-[1,1':3',1''-terphenyl]-2-carboxylic acid

aSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
Correspondence e-mail: ishi206@u-shizuoka-ken.ac.jp

In the title m-terphenyl derivative, C22H17NO4, the dihedral angles between the aromatic rings of the benzoic acid-acetophenone, acetophenone-benzamide and benzoic acid-benzamide units are 45.39 (8), 48.02 (8) and 42.93 (8)°, respectively. The carbamoyl and carboxyl groups are disordered with a refined occupancy ratio of 0.558 (15):0.442 (15). In the crystal, molecules are linked through O-H...O and N-H...O hydrogen bonds between terminal carboxyl and carbamoyl groups in a bidentate manner, and antiparallel helices are formed which extend along the b-axis direction.

Related literature

For background to this study, see: Ishikawa & Fujii (2011[Ishikawa, Y. & Fujii, S. (2011). Bioinformation, 6, 221-225.]). For related structures, see: Schnobrich et al. (2010[Schnobrich, J. K., Lebel, O., Cychosz, K. A., Dailly, A., Wong-Foy, A. G. & Matzger, A. J. (2010). J. Am. Chem. Soc. 132, 13941-13948.]); Fun et al. (2012[Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o163.]); Liu et al. (2013[Liu, Y., Li, J. R., Verdegaal, W. M., Liu, T. F. & Zhou, H. C. (2013). Chemistry, 19, 5637-5643.]). For the biological activity of a related compound, see: Tomassini et al. (1994[Tomassini, J., Selnick, H., Davies, M. E., Armstrong, M. E., Baldwin, J., Bourgeois, M., Hastings, J., Hazuda, D., Lewis, J., McClements, W., Ponticello, G., Radzilowski, E., Smith, G., Tebben, A. & Wolfe, A. (1994). Antimicrob. Agents Chemother. 38, 2827-2837.]).

[Scheme 1]

Experimental

Crystal data
  • C22H17NO4

  • Mr = 359.38

  • Monoclinic, P 21 /c

  • a = 13.076 (4) Å

  • b = 20.581 (5) Å

  • c = 6.725 (3) Å

  • [beta] = 104.10 (3)°

  • V = 1755.2 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 100 K

  • 0.38 × 0.25 × 0.20 mm

Data collection
  • Rigaku AFC-7R diffractometer

  • 4953 measured reflections

  • 4026 independent reflections

  • 2389 reflections with F2 > 2[sigma](F2)

  • Rint = 0.014

  • 3 standard reflections every 150 reflections intensity decay: 0.6%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.132

  • S = 1.01

  • 4026 reflections

  • 284 parameters

  • 10 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O25A-H25A...O27Ai 0.84 1.72 2.544 (9) 168
O25B-H25B...O27Bi 0.84 1.72 2.546 (8) 167
N23A-H23A...O24Aii 0.88 1.80 2.661 (8) 166
N23B-H23C...O24Bii 0.88 1.83 2.667 (10) 161
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: WinAFC (Rigaku, 1999[Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.]); cell refinement: WinAFC; data reduction: WinAFC; program(s) used to solve structure: SIR2008 (Burla et al., 2007[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RN2118 ).


Acknowledgements

This work was partly supported by Grants-in-Aid (No. 24590141 to YI) for Scientific Research from the Japan Society for the Promotion of Science. We acknowledge the University of Shizuoka for instrumental support.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o163.  [CSD] [CrossRef] [IUCr Journals]
Ishikawa, Y. & Fujii, S. (2011). Bioinformation, 6, 221-225.  [CrossRef] [PubMed]
Liu, Y., Li, J. R., Verdegaal, W. M., Liu, T. F. & Zhou, H. C. (2013). Chemistry, 19, 5637-5643.  [ChemPort] [PubMed]
Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Schnobrich, J. K., Lebel, O., Cychosz, K. A., Dailly, A., Wong-Foy, A. G. & Matzger, A. J. (2010). J. Am. Chem. Soc. 132, 13941-13948.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Tomassini, J., Selnick, H., Davies, M. E., Armstrong, M. E., Baldwin, J., Bourgeois, M., Hastings, J., Hazuda, D., Lewis, J., McClements, W., Ponticello, G., Radzilowski, E., Smith, G., Tebben, A. & Wolfe, A. (1994). Antimicrob. Agents Chemother. 38, 2827-2837.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1596  [ doi:10.1107/S1600536813026482 ]

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