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Volume 69 
Part 1 
Pages o127-o128  
January 2013  

Received 5 November 2012
Accepted 14 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.099
Data-to-parameter ratio = 14.5
Details
Open access

1,5-Dimethyl-2-phenyl-1H-pyrazol-3(2H)-one-4,4'-(propane-2,2-diyl)bis[1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one] (1/1)

aInstitute of Nuclear Chemistry and Technology, Dorodna 16, 03-195 Warsaw, Poland
Correspondence e-mail: k.lyczko@ichtj.waw.pl

The asymmetric unit of the title compound, C11H12N2O·C25H28N4O2, contains two different molecules. The smaller is known as antipyrine [systematic name: 1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one] and the larger is built up from two antypirine molecules which are connected through a C atom of the pyrazolone ring to a central propanyl part [systematic name: 4,4'-(propane-2,2-diyl)bis[1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one]. Intramolecular C-H...O hydrogen bonds occur in the latter molecule. In the crystal, C-H...O hydrogen bonds link the molecules into a two-dimensional network parallel to (001).

Related literature

Structural data on metal complexes with antipyrine were reported by Vijayan & Viswamitra (1966[Vijayan, M. & Viswamitra, M. A. (1966). Acta Cryst. 21, 522-532.]); Biagini Cingi et al. (1972[Cingi, M. B., Guastini, C., Musatti, A. & Nardelli, M. (1972). Acta Cryst. B28, 667-672.]); Baker & Jeffery (1974[Baker, R. W. & Jeffery, J. W. (1974). J. Chem. Soc. Dalton Trans. pp. 229-232.]); Brassy et al. (1974[Brassy, C., Renaud, A., Delettré, J. & Mornon, J.-P. (1974). Acta Cryst. B30, 2246-2248.]); Mahadevan et al. (1984[Mahadevan, C., Radha, A. & Seshasayee, M. (1984). Z. Kristallogr. 169, 159-163.]); Rheingold & King (1989[Rheingold, A. L. & King, W. (1989). Inorg. Chem. 28, 1715-1719.]) and Su et al. (2000[Su, C.-Y., Yang, X.-P., Xu, A.-W., Zhang, Z.-F., Liu, H.-K. & Kang, B.-S. (2000). Acta Cryst. C56, e82-e83.]). For related structures, see: Singh & Vijayan (1973[Singh, T. P. & Vijayan, M. (1973). Acta Cryst. B29, 714-720.]); Panneerselvam et al. (1996[Panneerselvam, K., Jayanthi, N., Rudiño-Piñera, E. & Soriano-García, M. (1996). Acta Cryst. C52, 1257-1258.]); Merz (2002[Merz, K. (2002). Acta Cryst. E58, o338-o340.]); Yuchi et al. (1991[Yuchi, A., Shiro, M., Wada, H. & Nakagawa, G. (1991). Bull. Chem. Soc. Jpn, 64, 760-765.]). Some properties of antipyrine and its derivatives were described by Peter et al. (1991[Peter, J. V. St., Abul-Hajj, Y. & Awni, W. M. (1991). Pharm. Res. 8, 1470-1476.]).

[Scheme 1]

Experimental

Crystal data
  • C11H12N2O·C25H28N4O2

  • Mr = 604.74

  • Monoclinic, P 21 /n

  • a = 11.1751 (3) Å

  • b = 7.4623 (2) Å

  • c = 37.2830 (8) Å

  • [beta] = 91.570 (2)°

  • V = 3107.93 (14) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.67 mm-1

  • T = 100 K

  • 0.30 × 0.25 × 0.15 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.938, Tmax = 1.000

  • 12009 measured reflections

  • 6009 independent reflections

  • 5366 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.099

  • S = 1.03

  • 6009 reflections

  • 414 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O1i 0.95 2.50 3.2949 (17) 142
C5-H5C...O2 0.98 2.44 3.3930 (17) 163
C10-H10...O3ii 0.95 2.53 3.4670 (18) 171
C14-H14A...O3 0.98 2.45 3.1228 (17) 126
C14-H14B...O2 0.98 2.34 3.0275 (17) 126
C21-H21...O1iii 0.95 2.49 3.3428 (18) 150
C25-H25...O2 0.95 2.37 2.8811 (17) 113
C29-H29B...O3iv 0.98 2.38 3.2956 (17) 155
C30-H30A...O3iv 0.98 2.32 3.3015 (16) 176
Symmetry codes: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x+1, y+1, z; (iii) x-1, y-1, z; (iv) x, y+1, z.

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2216 ).


Acknowledgements

The author thanks the Institute of Nuclear Chemistry and Technology for financial support.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Baker, R. W. & Jeffery, J. W. (1974). J. Chem. Soc. Dalton Trans. pp. 229-232.  [CrossRef]
Brassy, C., Renaud, A., Delettré, J. & Mornon, J.-P. (1974). Acta Cryst. B30, 2246-2248.  [CrossRef] [details] [ISI]
Cingi, M. B., Guastini, C., Musatti, A. & Nardelli, M. (1972). Acta Cryst. B28, 667-672.  [CrossRef] [details] [ISI]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Mahadevan, C., Radha, A. & Seshasayee, M. (1984). Z. Kristallogr. 169, 159-163.  [CrossRef] [ChemPort]
Merz, K. (2002). Acta Cryst. E58, o338-o340.  [CrossRef] [details]
Panneerselvam, K., Jayanthi, N., Rudiño-Piñera, E. & Soriano-García, M. (1996). Acta Cryst. C52, 1257-1258.  [CSD] [CrossRef] [details]
Peter, J. V. St., Abul-Hajj, Y. & Awni, W. M. (1991). Pharm. Res. 8, 1470-1476.  [PubMed]
Rheingold, A. L. & King, W. (1989). Inorg. Chem. 28, 1715-1719.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singh, T. P. & Vijayan, M. (1973). Acta Cryst. B29, 714-720.  [CrossRef] [ChemPort] [details] [ISI]
Su, C.-Y., Yang, X.-P., Xu, A.-W., Zhang, Z.-F., Liu, H.-K. & Kang, B.-S. (2000). Acta Cryst. C56, e82-e83.  [CSD] [CrossRef] [details]
Vijayan, M. & Viswamitra, M. A. (1966). Acta Cryst. 21, 522-532.  [CrossRef] [ChemPort] [details]
Yuchi, A., Shiro, M., Wada, H. & Nakagawa, G. (1991). Bull. Chem. Soc. Jpn, 64, 760-765.  [CrossRef] [ChemPort] [ISI]


Acta Cryst (2013). E69, o127-o128   [ doi:10.1107/S160053681205091X ]

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