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Volume 66 
Part 3 
Page o613  
March 2010  

Received 4 February 2010
Accepted 9 February 2010
Online 13 February 2010

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Key indicators
Powder X-ray study
T = 295 K
Mean [sigma](C-C) = 0.014 Å
R = 0.020
wR = 0.026
Data-to-parameter ratio = 44.5
Details
Open access

Carvedilol dihydrogen phosphate propan-2-ol solvate from powder diffraction data

Vladimir V. Chernyshev,a* Sergei Yu. Kukushkinb and Yurii A. Velikodnya

aDepartment of Chemistry, Moscow State University, 119991 Moscow, Russian Federation, and bBION Ltd, 109 km., Kiev Highway, Obninsk 249032, Kaluga Region, Russian Federation
Correspondence e-mail: vladimir@struct.chem.msu.ru

In the cation of the title compound, C24H27N2O4+·H2PO4-·C3H8O [systematic name: 3-(9H-carbazol-4-yloxy)-2-hydroxy-N-[2-(2-methoxyphenoxy)ethyl]propan-1-aminium dihydrogen phosphate propan-2-ol solvate], the mean planes of the tricyclic carbazole system and the benzene ring form a dihedral angle of 42.00 (16)°. In the crystal structure, classical intermolecular O-H...O and N-H...O hydrogen bonds link the cations, anions and solvent molecules into layers parallel to the ac plane.

Related literature

For details of the synthesis, see: Brook et al. (2005[Brook, C. S., Chen, W., Dell'Orco, P. C., Katrincic, L. M., Lovet, A. M., Oh, C. K., Spoors, P. G. & Werner, C. (2005). US Patent 20050240027A1.]). For the indexing algorithm, see: Werner et al. (1985[Werner, P.-E., Eriksson, L. & Westdahl, M. (1985). J. Appl. Cryst. 18, 367-370.]). For the crystal structures of carvedilol as a free base and a cation, see: Chen et al. (1998[Chen, W.-M., Zeng, L.-M., Yu, K.-B. & Xu, J.-H. (1998). Jiegou Huaxue, 17, 325-328.]); Yathirajan et al. (2007[Yathirajan, H. S., Bindya, S., Sreevidya, T. V., Narayana, B. & Bolte, M. (2007). Acta Cryst. E63, o542-o544.]); Chernyshev et al. (2009[Chernyshev, V. V., Machula, A. A., Kukushkin, S. Y. & Velikodny, Y. A. (2009). Acta Cryst. E65, o2020-o2021.]).

[Scheme 1]

Experimental

Crystal data

  • C24H27N2O4+·H2PO4-·C3H8O

  • Mr = 564.56

  • Triclinic, [P \overline 1]

  • a = 11.5516 (11) Å

  • b = 16.6523 (19) Å

  • c = 7.8643 (8) Å

  • [alpha] = 95.404 (15)°

  • [beta] = 94.635 (16)°

  • [gamma] = 71.247 (14)°

  • V = 1424.1 (3) Å3

  • Z = 2

  • Cu K[alpha]1 radiation, [lambda] = 1.54059 Å

  • [mu] = 1.32 mm-1

  • T = 295 K

  • flat_sheet, 15 × 1 mm
Data collection

  • G670 Guinier camera imaging plate diffractometer

  • Specimen mounting: thin layer in the specimen holder of the camera

  • Data collection mode: transmission

  • Scan method: continuous

  • 2[theta]min = 3.50°, 2[theta]max = 85.00°, 2[theta]step = 0.01°
Refinement

  • Rp = 0.020

  • Rwp = 0.026

  • Rexp = 0.012

  • RBragg = 0.051

  • [chi]2 = 4.516

  • 8151 data points

  • 183 parameters

  • 134 restraints

  • H-atom parameters constrained

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O18-H18...O34 0.82 1.89 2.681 (10) 165
N19-H19A...O34i 0.90 1.75 2.568 (10) 149
N19-H19B...O18 0.90 2.46 2.772 (11) 101
N19-H19B...O22 0.90 2.29 2.646 (10) 103
O32-H32...O33ii 0.82 1.90 2.672 (10) 156
O35-H35...O36iii 0.82 1.99 2.619 (9) 132
O36-H36...O33 0.82 2.00 2.590 (9) 128
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x-1, -y+1, -z+1; (iii) -x-1, -y+1, -z.

Data collection: G670 Imaging Plate Guinier Camera Software (Huber, 2002[Huber (2002). G670 Imaging Plate Guinier Camera Software. Huber Diffraktionstechnik GmbH, Rimsting, Germany.]); cell refinement: MRIA (Zlokazov & Chernyshev, 1992[Zlokazov, V. B. & Chernyshev, V. V. (1992). J. Appl. Cryst. 25, 447-451.]); data reduction: G670 Imaging Plate Guinier Camera Software; method used to solve structure: simulated annealing (Zhukov et al., 2001[Zhukov, S. G., Chernyshev, V. V., Babaev, E. V., Sonneveld, E. J. & Schenk, H. (2001). Z. Kristallogr. 216, 5-9.]); program(s) used to refine structure: MRIA; molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: MRIA and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YA2118 ).

Acknowledgements

VVC and YAV acknowledge the International Centre for Diffraction Data (ICDD) for supporting this study (grant No. GiA 03-06).

References

Brook, C. S., Chen, W., Dell'Orco, P. C., Katrincic, L. M., Lovet, A. M., Oh, C. K., Spoors, P. G. & Werner, C. (2005). US Patent 20050240027A1.
Chen, W.-M., Zeng, L.-M., Yu, K.-B. & Xu, J.-H. (1998). Jiegou Huaxue, 17, 325-328.  [ChemPort]
Chernyshev, V. V., Machula, A. A., Kukushkin, S. Y. & Velikodny, Y. A. (2009). Acta Cryst. E65, o2020-o2021.  [CSD] [CrossRef] [details]
Dollase, W. A. (1986). J. Appl. Cryst. 19, 267-272.  [CrossRef] [ChemPort] [ISI] [details]
Huber (2002). G670 Imaging Plate Guinier Camera Software. Huber Diffraktionstechnik GmbH, Rimsting, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Toraya, H. (1986). J. Appl. Cryst. 19, 440-447.  [CrossRef] [details]
Werner, P.-E., Eriksson, L. & Westdahl, M. (1985). J. Appl. Cryst. 18, 367-370.  [CrossRef] [details]
Yathirajan, H. S., Bindya, S., Sreevidya, T. V., Narayana, B. & Bolte, M. (2007). Acta Cryst. E63, o542-o544.  [CSD] [CrossRef] [details]
Zhukov, S. G., Chernyshev, V. V., Babaev, E. V., Sonneveld, E. J. & Schenk, H. (2001). Z. Kristallogr. 216, 5-9.  [CrossRef] [ChemPort]
Zlokazov, V. B. & Chernyshev, V. V. (1992). J. Appl. Cryst. 25, 447-451.  [CrossRef] [details]

Acta Cryst (2010). E66, o613  [ doi:10.1107/S1600536810005349 ]

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