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Volume 69 
Part 1 
Pages o12-o13  
January 2013  

Received 28 November 2012
Accepted 29 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.003 Å
R = 0.055
wR = 0.163
Data-to-parameter ratio = 25.6
Details
Open access

Bosentan monohydrate

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PP Box 77000, Port Elizabeth 6031, South Africa, and dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C27H29N5O6S·H2O {systematic name: 4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzene-1-sulfonamide monohydrate], the dihedral angle between the mean planes of the pyrimidine rings is 27.0 (1)°. The dihedral angle between the mean planes of the benzene rings is 47.7 (8)°, forming a U-shaped channel around the chain of twisted pyrimidine rings. The crystal packing is stabilized by O-H...O, O-H...N and N-H...O hydrogen bonds with a single water molecule, and weak O-H...N intermolecular interactions between the hydroxy group and one of the pyrimidine rings producing an two-dimensional supramolecular array in the bc plane. The title compound studied was a merohedral twin with the major component being approximately 57%.

Related literature

For reviews of bosentan in the management of pulmonary arterial hypertension and systemic sclerosis, see: Gabbay et al. (2007[Gabbay, E., Fraser, J. & McNeil, K. (2007). Vasc. Health Risk Manag. 3, 887-900.]); Kumar et al. (2011[Kumar, D., Sreenivas, S. A., Samal, H. B., Dey, S. & Yellamanchalli, P. (2011). J. Pharm. Res. 4, 1713-1715.]); Oldfield & Lyseng-Williamson (2006[Oldfield, V. & Lyseng-Williamson, K. A. (2006). Am. J. Cardiovasc. Drugs, 6, 189-208.]). For related structures, see: Singh et al. (1985[Singh, T. P., Tiwari, R. K. & Singh, M. (1985). Acta Cryst. C41, 752-755.]); El-Ghamry et al. (2008[El-Ghamry, H., Issa, R., El-Baradie, K., Isagai, K., Masaoka, S. & Sakai, K. (2008). Acta Cryst. E64, o1673-o1674.]); Kant et al. (2012[Kant, R., Gupta, V. K., Kapoor, K., Kumar, M., Mallesha, L. & Sridhar, M. A. (2012). Acta Cryst. E68, o2590-o2591.]).

[Scheme 1]

Experimental

Crystal data
  • C27H29N5O6S·H2O

  • Mr = 569.63

  • Monoclinic, P 21 /c

  • a = 12.3393 (4) Å

  • b = 15.1238 (6) Å

  • c = 14.6988 (4) Å

  • [beta] = 95.037 (3)°

  • V = 2732.46 (16) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.52 mm-1

  • T = 123 K

  • 0.79 × 0.43 × 0.22 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: analytical (CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED Agilent Technologies, Yarnton, England.]) Tmin = 0.535, Tmax = 0.766

  • 9563 measured reflections

  • 9563 independent reflections

  • 7477 reflections with I > 2[sigma](I)

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.163

  • S = 1.03

  • 9563 reflections

  • 373 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.77 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O6-H6...N3i 0.84 2.51 3.317 (2) 162
O6-H6...N4i 0.84 2.60 3.141 (2) 124
O1W-H1W...O4 0.80 (2) 2.30 (2) 3.013 (2) 150 (3)
O1W-H2W...N4ii 0.81 (2) 2.07 (2) 2.873 (2) 174 (3)
N1-H1A...O1W 0.88 1.87 2.721 (2) 163
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED Agilent Technologies, Yarnton, England.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5176 ).


Acknowledgements

MK thanks the UOM for research facilities. RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED Agilent Technologies, Yarnton, England.
El-Ghamry, H., Issa, R., El-Baradie, K., Isagai, K., Masaoka, S. & Sakai, K. (2008). Acta Cryst. E64, o1673-o1674.  [CSD] [CrossRef] [details]
Gabbay, E., Fraser, J. & McNeil, K. (2007). Vasc. Health Risk Manag. 3, 887-900.  [PubMed] [ChemPort]
Kant, R., Gupta, V. K., Kapoor, K., Kumar, M., Mallesha, L. & Sridhar, M. A. (2012). Acta Cryst. E68, o2590-o2591.  [CSD] [CrossRef] [details]
Kumar, D., Sreenivas, S. A., Samal, H. B., Dey, S. & Yellamanchalli, P. (2011). J. Pharm. Res. 4, 1713-1715.  [ChemPort]
Oldfield, V. & Lyseng-Williamson, K. A. (2006). Am. J. Cardiovasc. Drugs, 6, 189-208.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singh, T. P., Tiwari, R. K. & Singh, M. (1985). Acta Cryst. C41, 752-755.  [CrossRef] [details]


Acta Cryst (2013). E69, o12-o13   [ doi:10.1107/S1600536812048969 ]

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