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Volume 69 
Part 11 
Page o1673  
November 2013  

Received 29 September 2013
Accepted 15 October 2013
Online 19 October 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.065
wR = 0.136
Data-to-parameter ratio = 14.7
Details
Open access

N-[5-(Di­phenyl­phosphorylmeth­yl)-4-(4-fluoro­phen­yl)-6-iso­propyl­pyrimi­din-2-yl]-N-methyl­methane­sulfonamide

aDepartment of Applied Chemistry, Nanjing College of Chemical Technology, No. 625 Geguan Road, Dachang, Nanjing 210048, People's Republic of China
Correspondence e-mail: adsony05@163.com

In the title compound, C28H29FN3O3PS, the pyrimidine ring is oriented at a dihedral angle of 50.9 (2)° with respect to the floro­benzene ring, while the two phenyl rings bonding to the same P atom are twisted with respect to each other, making a dihedral angle of 62.2 (2)°. In the crystal, mol­ecules are linked by weak C-H...O and C-H...F hydrogen bonds into a three-dimensional supra­molecular architecture.

Related literature

For the synthesis of the title compound, an inter­mediate for the preparation of the statin rosuvastation {systematic name: (3R,5S,6E)-7-[4-(4-fluoro­phen­yl)-2-(N-methyl­methane­sulfon­amido)-6-(propan-2-yl)pyrimidin-5-yl]-3,5-di­hydroxy­hept-6-enoic acid}, see: Brieden & Veith (2000[Brieden, W. & Veith, U. (2000). Eur. Patent EP1035127.]).

[Scheme 1]

Experimental

Crystal data
  • C28H29FN3O3PS

  • Mr = 537.57

  • Monoclinic, P 21 /n

  • a = 14.023 (3) Å

  • b = 6.3830 (13) Å

  • c = 30.493 (6) Å

  • [beta] = 102.79 (3)°

  • V = 2661.7 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 293 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.957, Tmax = 0.978

  • 5109 measured reflections

  • 4898 independent reflections

  • 2568 reflections with I > 2[sigma](I)

  • Rint = 0.092

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.065

  • wR(F2) = 0.136

  • S = 1.00

  • 4898 reflections

  • 334 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 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
C1-H1B...O1i 0.96 2.56 3.363 (5) 141
C2-H2C...Fii 0.96 2.52 3.202 (6) 128
C13-H13A...O2iii 0.93 2.53 3.350 (6) 148
Symmetry codes: (i) [-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+2, -y, -z; (iii) x-1, y, z.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5743 ).


Acknowledgements

The author thanks the Center of Testing and Analysis of Nanjing University for the data collection.

References

Brieden, W. & Veith, U. (2000). Eur. Patent EP1035127.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1673  [ doi:10.1107/S1600536813028286 ]

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.