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Volume 69 
Part 11 
Pages o1599-o1600  
November 2013  

Received 15 September 2013
Accepted 24 September 2013
Online 2 October 2013

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.002 Å
R = 0.048
wR = 0.140
Data-to-parameter ratio = 17.4
Details
Open access

2-(2,4-Di­fluoro­phen­yl)-4,5-dimethyl-1-(4-methyl­phen­yl)-1H-imidazole monohydrate

aDepartment of Chemistry, S.K.P. Engineering College, Thiruvanamalai 606 611, India,bDepartment of Physics, Seethalakshmi Ramaswami College (Autonomous), Tiruchirappalli 620 002, India,cDepartment of Physics, K. Ramakrishnan College of Engineering, Samayapuram, Tiruchirappalli 621 112, India, and dLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Correspondence e-mail: raghema2000@yahoo.co.in

The asymmetric unit of the title compound, C18H16F2N2·H2O, contains two independent mol­ecules (A and B), and two independent water mol­ecules of crystallization. In mol­ecule A, the imidazole ring makes dihedral angles of 47.46 (7) and 60.98 (6)° with the 2,4-di­fluoro­phenyl and methyl­phenyl rings, respectively. The corresponding angles in mol­ecule B are 45.85 (7) and 62.78 (7)°, respectively. The dihedral angle between the two benzene rings is 64.98 (7)° in mol­ecule A and 65.53 (7)° in mol­ecule B. In the crystal, the two independent mol­ecules are linked by O-H...N and O-H...O hydrogen bonds, forming chains propagating along [100]. These chains are linked via C-H...F hydrogen bonds, forming slab-like two-dimensional networks lying parallel to (001).

Related literature

For background and the biological properties of imidazole derivatives, see: Dutta et al. (2009[Dutta, S., Mariappan, G., Roy, S. & Verma, M. (2009). Indian Drugs, 46, 50-53.]); Hori et al. (2000[Hori, K., Sakaguchi, A., Kudoh, M., Ishida, K., Aoyama, Y. & Yoshida, Y. (2000). Chem. Pharm. Bull. 48, 60-64.]); Khabnadideh et al. (2003[Khabnadideh, S., Rezaeia, Z., Khalafi-Nezhadb, A., Bahrinajafia, R., Mohamadia, R. & Farrokhroza, A. A. (2003). Bioorg. Med. Chem. Lett. 13, 2863-2865.]); Mamolo et al. (2004[Mamolo, M. G., Zampieri, D., Falagiani, V., Vio, L., Fermeglia, M., Ferrone, M., Pricl, S., Banfi, E. & Scialino, G. (2004). ARKIVOC, v, 231-250.]); Quattara et al. (1987[Quattara, L., Debaert, M. & Cavier, R. (1987). Il Farmaco, 42, 449-456.]); Sengupta & Bhattacharya (1983[Sengupta, A. K. & Bhattacharya, T. (1983). J. Indian Chem. Soc. 60, 373-376.]); Ucucu et al. (2001[Ucucu, U., Karaburun, N. G. & Isikdag, I. (2001). Il Farmaco, 56, 285-290.]); Noilada et al. (2004[Noilada, A., Koyunoglu, S., Saygili, N., Kupeli, E., Noilada, E., Bedir, E. & Khan, I. (2004). Arch. Pharm. Pharm. Med. Chem. 337, 96-104.]). For related structures, see: Rizwana et al. (2013[Rizwana Begum, S., Hema, R., Srinivasan, N. & Anitha, A. G. (2013). Acta Cryst. E69, o1154.]); Gayathri et al. (2010[Gayathri, P., Jayabharathi, J., Srinivasan, N., Thiruvalluvar, A. & Butcher, R. J. (2010). Acta Cryst. E66, o1703.]); Rosepriya et al. (2011[Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J., Srinivasan, N., Butcher, R. J., Jasinski, J. P. & Golen, J. A. (2011). Acta Cryst. E67, o1065.]).

[Scheme 1]

Experimental

Crystal data
  • C18H16F2N2·H2O

  • Mr = 316.34

  • Triclinic, [P \overline 1]

  • a = 7.9424 (9) Å

  • b = 14.5238 (16) Å

  • c = 14.6561 (16) Å

  • [alpha] = 75.087 (2)°

  • [beta] = 89.990 (2)°

  • [gamma] = 86.012 (2)°

  • V = 1629.5 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 294 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • 18763 measured reflections

  • 7545 independent reflections

  • 5782 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.140

  • S = 1.00

  • 7545 reflections

  • 433 parameters

  • 13 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1W-H1WA...N5i 0.82 (3) 2.17 (3) 2.987 (2) 177 (2)
O1W-H1WB...O1Wii 0.72 (2) 2.42 (2) 2.894 (3) 125 (2)
O2W-H2WA...N3 0.84 (3) 2.16 (3) 2.995 (2) 174 (2)
O2W-H2WB...O2Wiii 0.73 (2) 2.42 (2) 2.910 (2) 126 (2)
C17-H17...F3iv 0.93 2.46 3.253 (2) 143
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y, -z+1; (iii) -x+1, -y, -z+1; (iv) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2650 ).


Acknowledgements

SR thanks the University Grants Commission for financial support of this work (grant MRP-4335/12).

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [IUCr Journals]
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dutta, S., Mariappan, G., Roy, S. & Verma, M. (2009). Indian Drugs, 46, 50-53.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gayathri, P., Jayabharathi, J., Srinivasan, N., Thiruvalluvar, A. & Butcher, R. J. (2010). Acta Cryst. E66, o1703.  [CSD] [CrossRef] [IUCr Journals]
Hori, K., Sakaguchi, A., Kudoh, M., Ishida, K., Aoyama, Y. & Yoshida, Y. (2000). Chem. Pharm. Bull. 48, 60-64.  [CrossRef] [PubMed] [ChemPort]
Khabnadideh, S., Rezaeia, Z., Khalafi-Nezhadb, A., Bahrinajafia, R., Mohamadia, R. & Farrokhroza, A. A. (2003). Bioorg. Med. Chem. Lett. 13, 2863-2865.  [CrossRef] [PubMed] [ChemPort]
Mamolo, M. G., Zampieri, D., Falagiani, V., Vio, L., Fermeglia, M., Ferrone, M., Pricl, S., Banfi, E. & Scialino, G. (2004). ARKIVOC, v, 231-250.  [CrossRef]
Noilada, A., Koyunoglu, S., Saygili, N., Kupeli, E., Noilada, E., Bedir, E. & Khan, I. (2004). Arch. Pharm. Pharm. Med. Chem. 337, 96-104.
Quattara, L., Debaert, M. & Cavier, R. (1987). Il Farmaco, 42, 449-456.  [ChemPort]
Rizwana Begum, S., Hema, R., Srinivasan, N. & Anitha, A. G. (2013). Acta Cryst. E69, o1154.  [CSD] [CrossRef] [IUCr Journals]
Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J., Srinivasan, N., Butcher, R. J., Jasinski, J. P. & Golen, J. A. (2011). Acta Cryst. E67, o1065.  [CSD] [CrossRef] [IUCr Journals]
Sengupta, A. K. & Bhattacharya, T. (1983). J. Indian Chem. Soc. 60, 373-376.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Ucucu, U., Karaburun, N. G. & Isikdag, I. (2001). Il Farmaco, 56, 285-290.  [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1599-o1600   [ doi:10.1107/S1600536813026354 ]

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