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)

Lyczko, K.

doi:10.1107/S160053681205091X

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 (C-C) = 0.002 Å
R = 0.040
wR = 0.099
Data-to-parameter ratio = 14.5
Details

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)

Krzysztof Lyczko ^a ^*

^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-HO hydrogen bonds occur in the latter molecule. In the crystal, C-HO 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); Biagini Cingi et al. (1972); Baker & Jeffery (1974); Brassy et al. (1974); Mahadevan et al. (1984); Rheingold & King (1989) and Su et al. (2000). For related structures, see: Singh & Vijayan (1973); Panneerselvam et al. (1996); Merz (2002); Yuchi et al. (1991). Some properties of antipyrine and its derivatives were described by Peter et al. (1991).

Experimental

Crystal data

C₁₁H₁₂N₂O·C₂₅H₂₈N₄O₂
M_r = 604.74
Monoclinic, P 2₁ /n
a = 11.1751 (3) Å
b = 7.4623 (2) Å
c = 37.2830 (8) Å
= 91.570 (2)°
V = 3107.93 (14) Å³
Z = 4
Cu K radiation
= 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) T_min = 0.938, T_max = 1.000
12009 measured reflections
6009 independent reflections
5366 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.099
S = 1.03
6009 reflections
414 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2O1ⁱ	0.95	2.50	3.2949 (17)	142
C5-H5CO2	0.98	2.44	3.3930 (17)	163
C10-H10O3ⁱⁱ	0.95	2.53	3.4670 (18)	171
C14-H14AO3	0.98	2.45	3.1228 (17)	126
C14-H14BO2	0.98	2.34	3.0275 (17)	126
C21-H21O1ⁱⁱⁱ	0.95	2.49	3.3428 (18)	150
C25-H25O2	0.95	2.37	2.8811 (17)	113
C29-H29BO3^iv	0.98	2.38	3.2956 (17)	155
C30-H30AO3^iv	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); 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.
Brassy, C., Renaud, A., Delettré, J. & Mornon, J.-P. (1974). Acta Cryst. B30, 2246-2248.
Cingi, M. B., Guastini, C., Musatti, A. & Nardelli, M. (1972). Acta Cryst. B28, 667-672.
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.
Mahadevan, C., Radha, A. & Seshasayee, M. (1984). Z. Kristallogr. 169, 159-163.
Merz, K. (2002). Acta Cryst. E58, o338-o340.
Panneerselvam, K., Jayanthi, N., Rudiño-Piñera, E. & Soriano-García, M. (1996). Acta Cryst. C52, 1257-1258.
Peter, J. V. St., Abul-Hajj, Y. & Awni, W. M. (1991). Pharm. Res. 8, 1470-1476.
Rheingold, A. L. & King, W. (1989). Inorg. Chem. 28, 1715-1719.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Singh, T. P. & Vijayan, M. (1973). Acta Cryst. B29, 714-720.
Su, C.-Y., Yang, X.-P., Xu, A.-W., Zhang, Z.-F., Liu, H.-K. & Kang, B.-S. (2000). Acta Cryst. C56, e82-e83.
Vijayan, M. & Viswamitra, M. A. (1966). Acta Cryst. 21, 522-532.
Yuchi, A., Shiro, M., Wada, H. & Nakagawa, G. (1991). Bull. Chem. Soc. Jpn, 64, 760-765.