[2-Acet­oxy-3-(naphthalen-1-yl­oxy)prop­yl](propan-2-yl)aza­nium chloride monohydrate

Yuan-Yuan Liu; Guang-Hui Xu; Zheng-Jie Li; Hong-Yu Xu; Chang-Qing Gu

doi:10.1107/S1600536813005515

. 2013 Mar 9;69(Pt 4):o512. doi: 10.1107/S1600536813005515

[2-Acetoxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)azanium chloride monohydrate

Yuan-Yuan Liu ^a,^*, Guang-Hui Xu ^a, Zheng-Jie Li ^a, Hong-Yu Xu ^a, Chang-Qing Gu ^a

PMCID: PMC3629540 PMID: 23634058

Abstract

The title compound, C₁₈H₂₄NO₃ ⁺·Cl⁻·H₂O, was synthesized by the reaction of propranolol hydrochloride with acetyl chloride in chloroform followed by slow evaporation in air. In the cation, the dihedral angle between the planes of the naphthalene ring system and the acetate group is 71.1 (2)°. An intramolecular N—H⋯O hydrogen bond results in the formation of a non-planar pseudo-ring, with the ether O and the H atom displaced by −1.328 (2) and 0.65 Å, respectively, from the plane of the other ring atoms. The cation and anion are linked by an N—H⋯Cl hydrogen bond. The water molecule is linked to a methyl H atom by C—H⋯O hydrogen bond.

Related literature

The applications of the title compound, see: Barbosa et al. (2010 ▶). For the synthetic procedure, see: Irwin & Belaid (1987 ▶). For bond-length data, see: Allen et al. (1987 ▶). graphic file with name e-69-0o512-scheme1.jpg

Experimental

Crystal data

C₁₈H₂₄NO₃ ⁺·Cl⁻·H₂O
M _r = 355.85
Monoclinic,
a = 15.559 (3) Å
b = 8.2120 (16) Å
c = 14.665 (3) Å
β = 93.23 (3)°
V = 1870.8 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.936, T _max = 0.978
3424 measured reflections
3424 independent reflections
1948 reflections with I > 2σ(I)
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.070
wR(F ²) = 0.200
S = 0.99
3424 reflections
219 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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

Click here for additional data file.^{(20.2KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813005515/bq2383sup1.cif

e-69-0o512-sup1.cif^{(20.2KB, cif)}

Click here for additional data file.^{(171.3KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005515/bq2383Isup2.hkl

e-69-0o512-Isup2.hkl^{(171.3KB, hkl)}

Click here for additional data file.^{(6.8KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813005515/bq2383Isup3.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
N—H0A⋯Cl	0.90	2.37	3.194 (3)	152
N—H0A⋯O2	0.90	2.59	2.948 (3)	105
C15—H15B⋯O1W ⁱ	0.96	2.53	3.469 (9)	166

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

supplementary crystallographic information

Comment

Propranolol hydrochloride is an important beta-adrenergic blocking agent, and used in the treatment of hypertension and cardiovascular disorders. Molecular modifications of propranolol are varied with examples in the amino-substituent, side-chain variants and nuclear changes including all mono ring-hydroxylated products (Irwin et al., 1987). Here, the title compound, (I), an important propranolol derivative, was synthesized by the reaction of propranolol hydrochloride with acetyl chloride in chloroform, and we report the crystal structure of (I).

In the molecule of (I), (Fig.1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The dihedral angle of naphthalene ring system and acetate group is 71.11 °. The amino hydrogen is linked to chloride and oxygen atoms by the intramolecular N—H···Cl and N—H···O hydrogen bonds, respectively, which seem to be very effective in the stabilization of the crystal structure. The intramolecular N—H···O hydrogen bond results in the formation of one non-planar pseudo ring (O2/C12/C13/N/H0A), with O2 and H0A atoms displaced by -1.328 Å and 0.65 Å, respectively, from the plane of the other ring atoms.

Experimental

The title compound, (I) was prepared by the literature method (Irwin et al., 1987). Crystals suitable for X-ray analysis were obtained by dissolving (I) (0.5 g) in methanol (20 ml) and evaporating the solvent slowly at room temperature for about 10 d.