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Volume 67 
Part 7 
Page o1598  
July 2011  

Received 31 May 2011
Accepted 1 June 2011
Online 11 June 2011

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.042
wR = 0.117
Data-to-parameter ratio = 32.1
Details
Open access

Opipramol

Hoong-Kun Fun,a*+ Wan-Sin Loh,a++ M. S. Siddegowda,b H. S. Yathirajanb and B. Narayanac

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
Correspondence e-mail: hkfun@usm.my

In the title compound (systematic name: 2-{4-[3-(5H-dibenz[b,f]azepin-5-yl)propyl]piperazin-1-yl}ethanol), C23H29N3O, the 5H-dibenz[b,f]azepine and piperazine rings adopt boat and chair conformations, respectively, and the overall shape of the fused ring part of the molecule is a butterfly. In the crystal, O-H...N and C-H...O hydrogen bonds link the molecules into a layer parallel to the bc plane.

Related literature

For the application of opipramol, see: Moller et al. (2001[Moller, H. J., Volz, H. P., Reimann, I. W. & Stoll, K. D. (2001). J. Clin. Psychopharmacol. 21, 59-65.]). For related structures, see: Jasinski et al. (2010[Jasinski, J. P., Pek, A. E., Siddaraju, B. P., Yathirajan, H. S. & Narayana, B. (2010). Acta Cryst. E66, o1979-o1980.]); Nagaraj et al. (2005[Nagaraj, B., Yathirajan, H. S. & Lynch, D. E. (2005). Acta Cryst. E61, o1757-o1759.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C23H29N3O

  • Mr = 363.49

  • Monoclinic, P 21 /c

  • a = 12.6215 (2) Å

  • b = 10.5929 (2) Å

  • c = 14.3629 (2) Å

  • [beta] = 90.966 (1)°

  • V = 1920.02 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.59 × 0.36 × 0.30 mm
Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.955, Tmax = 0.977

  • 30830 measured reflections

  • 7949 independent reflections

  • 6682 reflections with I > 2[sigma](I)

  • Rint = 0.026
Refinement

  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.117

  • S = 1.03

  • 7949 reflections

  • 248 parameters

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

  • [Delta][rho]max = 0.56 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1O1...N2i 0.896 (16) 1.999 (16) 2.8822 (9) 168.3 (14)
C5-H5A...O1ii 0.95 2.41 3.3478 (11) 167
Symmetry codes: (i) [x, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2726 ).

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). WSL also thanks the Malaysian government and USM for the award of a research fellowship. MSS thanks UOM for research facilities.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Jasinski, J. P., Pek, A. E., Siddaraju, B. P., Yathirajan, H. S. & Narayana, B. (2010). Acta Cryst. E66, o1979-o1980.  [CSD] [CrossRef] [details]
Moller, H. J., Volz, H. P., Reimann, I. W. & Stoll, K. D. (2001). J. Clin. Psychopharmacol. 21, 59-65.  [ISI] [CrossRef] [PubMed] [ChemPort]
Nagaraj, B., Yathirajan, H. S. & Lynch, D. E. (2005). Acta Cryst. E61, o1757-o1759.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2011). E67, o1598  [ doi:10.1107/S1600536811021131 ]

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