Opipramol

Hoong-Kun Fun; Wan-Sin Loh; M S Siddegowda; H S Yathirajan; B Narayana

doi:10.1107/S1600536811021131

. 2011 Jun 11;67(Pt 7):o1598. doi: 10.1107/S1600536811021131

Opipramol

Hoong-Kun Fun ^a,^*,^‡, Wan-Sin Loh ^a,^§, M S Siddegowda ^b, H S Yathirajan ^b, B Narayana ^c

PMCID: PMC3151965 PMID: 21837006

Abstract

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 ▶). For related structures, see: Jasinski et al. (2010 ▶); Nagaraj et al. (2005 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₃H₂₉N₃O
M _r = 363.49
Monoclinic,
a = 12.6215 (2) Å
b = 10.5929 (2) Å
c = 14.3629 (2) Å
β = 90.966 (1)°
V = 1920.02 (5) Å³
Z = 4
Mo Kα radiation
μ = 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 ▶) T _min = 0.955, T _max = 0.977
30830 measured reflections
7949 independent reflections
6682 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.117
S = 1.03
7949 reflections
248 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811021131/is2726sup1.cif

e-67-o1598-sup1.cif^{(22.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021131/is2726Isup2.hkl

e-67-o1598-Isup2.hkl^{(388.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811021131/is2726Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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.

supplementary crystallographic information

Comment

Opipramol [systematic IUPAC name: 4-[3-(5H-dibenz[b,f] azepin-5-yl)propyl]-1-piperazinethanol] is an antidepressant and anxiolytic typically used in the treatment of generalized anxiety disorder (Moller et al., 2001). Opipramol is a tricyclic compound with no reuptake-inhibiting properties. However, it has pronounced D2-, 5-HT2-, and H1-blocking potential and high affinity to sigma receptors (sigma-1 and sigma-2). The crystal structure studies of opipramol dipicrate is reported (Jasinski et al., 2010). In view of the importance of the title compound, C₂₃H₂₉N₃O, the crystal structure is reported.

In the title compound (Fig. 1), the seven-membered, 5H-dibenz[b,f]azepine ring (N1/C1/C6–C9/C14) adopts a boat conformation (Cremer & Pople, 1975) and the overall molecular shape is that of a butterfly (Nagaraj et al., 2005) whereas the piperazine ring (N2/C18/C19/N3/C20/C21) adopts a chair conformation (Cremer & Pople, 1975) with the puckering parameters, Q = 0.5934 (8) Å, Θ = 177.94 (8)°, φ = 305.8 (18)°. The torsion angle between the 5H-dibenz[b,f]azepine and the piperazine rings, N1–C15–C16–C17 is 61.73 (8)°. Bond lengths (Allen et al., 1987) and angles are within the normal ranges.

In the crystal packing (Fig. 2), intermolecular O1—H1O1···N2 and C5—H5A···O1 hydrogen bonds link the molecules into layers parallel to the bc plane.

Experimental

The title compound was obtained as a gift sample from R. L. Fine Chem. Ltd., Bangalore, India. The compound was recrystallized from acetone (m. p. 373–374 K).