Cyclo­benzaprinium chloride

M S Siddegowda; Jerry P Jasinski; James A Golen; H S Yathirajan; M T Swamy

doi:10.1107/S1600536811024676

. 2011 Jun 30;67(Pt 7):o1846. doi: 10.1107/S1600536811024676

Cyclobenzaprinium chloride

M S Siddegowda ^a, Jerry P Jasinski ^b,^*, James A Golen ^b, H S Yathirajan ^a, M T Swamy ^c

PMCID: PMC3151785 PMID: 21837211

Abstract

In the title molecular salt [systematic name: 3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethylpropanaminium chloride], C₂₀H₂₂N⁺·Cl⁻, two cation–anion pairs make up the asymmetric unit. The dihedral angles between the mean planes of the two fused benzene rings of the cation are 49.5 (1) and 50.9 (1)°. The cystal packing is stabilized by N—H⋯Cl hydrogen bonds and weak C—H⋯Cl interactions.

Related literature

For structurally related tricyclic antidepressants, see: Cimolai (2009 ▶); Commissiong et al. (1981 ▶); Katz & Dube (1988 ▶). For related structures, see: Bindya et al. (2007 ▶); Fun et al. (2011 ▶); Portalone et al. (2007 ▶). For standard bond lengths, see Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₀H₂₂N⁺·Cl⁻
M _r = 311.84
Tetragonal,
a = 32.0959 (7) Å
c = 13.7578 (5) Å
V = 14172.6 (7) Å³
Z = 32
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 173 K
0.40 × 0.22 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T _min = 0.920, T _max = 0.959
62421 measured reflections
8426 independent reflections
6210 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.071
wR(F ²) = 0.198
S = 1.03
8426 reflections
407 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.00 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811024676/jh2300sup1.cif

e-67-o1846-sup1.cif^{(29.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024676/jh2300Isup2.hkl

e-67-o1846-Isup2.hkl^{(412.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811024676/jh2300Isup3.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
N1—H1N⋯Cl1	0.87 (2)	2.15 (2)	3.018 (2)	174 (2)
N2—H2N⋯Cl2	0.87 (2)	2.12 (2)	2.991 (2)	178 (3)
C19—H19B⋯Cl2ⁱ	0.98	2.83	3.702 (3)	149
C20—H20B⋯Cl2ⁱ	0.98	2.72	3.621 (3)	153
C38—H38B⋯Cl1	0.99	2.69	3.610 (3)	155

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Symmetry code: (i) Inline graphic .

Acknowledgments

MSS thanks the University of Mysore for the research facilities and HSY thanks R. L. Fine Chem, Bangalore, India, for the gift sample. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

Cyclobenzaprine (Systematic iupac name: N,N-dimethyl-3-(dibenzo[a,d]cyclohepten-5-ylidene)propylamine) is a muscle relaxant medication used to relieve skeletal muscle spasms and associated pain in acute musculoskeletal conditions. It is the most well-studied drug for this application and it also has been used off-label for fibromyalgia treatment. Cyclobenzaprine has been considered structurally related to the first-generation tricyclic antidepressants (Commissiong et al., 1981; Katz & Dube, 1988; Cimolai, 2009). The crystal structures of amitriptylinium picrate (Bindya et al., 2007), 5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[a,d][7]annulen-5-ol (Portalone et al., 2007) and cyclobenzaprinium salicylate (Fun et al., 2011) have been reported. In view of the importance of yclobenzaprine, this paper reports the crystal structure of the title compound, C₂₀H₂₂N⁺. Cl^-.

In the title molecular salt [Systematic name: 3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)- N,N-dimethyl-1-propanamine hydrochloride], C₂₀H₂₂N⁺. Cl^-, two cation-anion pairs crystallize in the asymmetric unit. The dihedral angle between the mean planes of the two fused benzene rings of the cation are 49.5 (1)° and 50.9 (1)°, respectively. Bond lengths are in normal positions (Allen et al., 1987). Cystal packing is stabilized by N—H···Cl hydrogen bonds and weak C—H···Cl intermolecular interactions (Fig. 2, Table 1).

Experimental

The title compound was obtained as a gift sample from R. L. Fine Chem, Bangalore. X-ray quality crystals were obtained by slow evaporation of (1:1) methanol and dichloromethane solution (m.p.: 458-460 K).