[Journal logo]

Volume 69 
Part 4 
Page o608  
April 2013  

Received 12 March 2013
Accepted 21 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 93 K
Mean [sigma](C-C) = 0.003 Å
R = 0.031
wR = 0.080
Data-to-parameter ratio = 8.3
Details
Open access

A new polymorph of 1,3-bis(pentafluorophenyl)urea

aDepartment of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama, 640-8510, Japan
Correspondence e-mail: okuno@center.wakayama-u.ac.jp

The title compound, C13H2F10N2O, has been previously described in the space group Pbca with Z = 8 [Jai-nhuknan et al. (1997[Jai-nhuknan, J., Karipides, A. G., Hughes, J. M. & Cantrell, J. S. (1997). Acta Cryst. C53, 455-457.]). Acta Cryst. C53, 455-457]. The current P212121 polymorph was obtained from a tetrahydrofuran solution. The pentafluorophenyl rings make dihedral angles of 50.35 (6) and 54.94 (6)° with the urea fragment, in close accord with those reported for the first polymorph. In the crystal, both of the N-H groups donate H atoms to the same carbonyl O atom, forming a one-dimensional molecular array along the a axis. There are close contacts between perfluorophenyl C atoms within the array [3.228 (3) Å] and halogen bonds are also observed between the arrays [F...F = 2.709 (2) and 2.7323 (18) Å].

Related literature

For the structure of the first reported ploymorph, see: Jai-nhuknan et al. (1997[Jai-nhuknan, J., Karipides, A. G., Hughes, J. M. & Cantrell, J. S. (1997). Acta Cryst. C53, 455-457.]). For the related structure of 1,3-diphenylurea, see: Dannecker et al. (1979[Dannecker, W., Kopf, J. & Rust, H. (1979). Cryst. Struct. Commun. 8, 429-432.]). For background to organofluorine chemistry, see: Chambers (2004[Chambers, R. D. (2004). In Fluorine in Organic Chemistry, ch. 9. Oxford: Blackwell Publishing Ltd.]).

[Scheme 1]

Experimental

Crystal data
  • C13H2F10N2O

  • Mr = 392.16

  • Orthorhombic, P 21 21 21

  • a = 4.5798 (7) Å

  • b = 9.5411 (16) Å

  • c = 29.136 (5) Å

  • V = 1273.1 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 93 K

  • 0.15 × 0.15 × 0.03 mm

Data collection
  • Rigaku Saturn724+ diffractometer

  • Absorption correction: numerical (NUMABS; Rigaku, 1999[Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.978, Tmax = 0.993

  • 10307 measured reflections

  • 1993 independent reflections

  • 1941 reflections with F2 > 2[sigma](F2)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.080

  • S = 1.09

  • 1991 reflections

  • 241 parameters

  • 2 restraints

  • Only H-atom coordinates refined

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.864 (18) 2.057 (18) 2.850 (3) 152 (3)
N2-H2...O1i 0.879 (18) 2.008 (18) 2.825 (3) 154 (3)
Symmetry code: (i) x+1, y, z.

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare, et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2101 ).


Acknowledgements

This work was supported by `Research for Promoting Technological Seeds' of the Japan Science and Technology Agency (JST).

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Chambers, R. D. (2004). In Fluorine in Organic Chemistry, ch. 9. Oxford: Blackwell Publishing Ltd.
Dannecker, W., Kopf, J. & Rust, H. (1979). Cryst. Struct. Commun. 8, 429-432.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jai-nhuknan, J., Karipides, A. G., Hughes, J. M. & Cantrell, J. S. (1997). Acta Cryst. C53, 455-457.  [CSD] [CrossRef] [details]
Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o608  [ doi:10.1107/S1600536813007836 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.