Crystal structure of [(2S)-1-[(3S)-3-carboxy-6,7-dimethoxy-1,2,3,4-tetra­hydroisoquinolin-2-yl]-1-oxopropan-2-yl][(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]azanium chloride acetonitrile monosolvate

Ai-zhen Li; Wen-jie Xu

doi:10.1107/S160053681402090X

. 2014 Sep 24;70(Pt 10):o1126–o1127. doi: 10.1107/S160053681402090X

Crystal structure of [(2S)-1-[(3S)-3-carboxy-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl]-1-oxopropan-2-yl][(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]azanium chloride acetonitrile monosolvate

Ai-zhen Li ^a, Wen-jie Xu ^a,^*

PMCID: PMC4257232 PMID: 25484709

Abstract

The title compound (trivial name moexipril hydrochloride) crystallizes as the acetonitrile monosolvate, C₂₇H₃₅N₂O₇ ⁺·Cl⁻·C₂H₃N, with the salt comprising a U-shaped cation and a chloride anion. The conformation of the cation is stabilized by a weak intramolecular N⁺—H⋯O hydrogen bond and the tetrahydropyridine ring adopts a boat conformation. The dihedral angle between the planes of the benzene rings is 85.6 (1)°. In the crystal, the cations and anions form tight ionic pairs by strong intermolecular O—H⋯Cl hydrogen bonds. C—H⋯Cl and C—H⋯N hydrogen bonds link these ionic pairs and the acetonitrile solvate molecules into puckered layers parallel to (100).

Keywords: crystal structure, moexipril hydrochloride, hydrogen bond

Related literature

For the synthesis of the title compound, see: Klutchko et al. (1986 ▶); Yamazaki & Suzuki (1998 ▶). For the structure and applications of related compounds, see: Suzuki et al. (2000 ▶, 2010 ▶). graphic file with name e-70-o1126-scheme1.jpg

Experimental

Crystal data

C₂₇H₃₅N₂O₇ ⁺·Cl⁻·C₂H₃N
M _r = 576.07
Monoclinic,
a = 10.9391 (6) Å
b = 10.4655 (4) Å
c = 13.3159 (5) Å
β = 97.419 (4)°
V = 1511.68 (12) Å³
Z = 2
Cu Kα radiation
μ = 1.52 mm⁻¹
T = 103 K
0.50 × 0.20 × 0.20 mm

Data collection

Agilent Xcalibur, Eos, Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.516, T _max = 0.750
11078 measured reflections
5728 independent reflections
5570 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.087
S = 1.03
5728 reflections
367 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.34 e Å⁻³
Absolute structure: Flack (1983 ▶), 2620 Friedel pairs
Absolute structure parameter: 0.000 (10)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681402090X/kq2014sup1.cif

e-70-o1126-sup1.cif^{(35.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681402090X/kq2014Isup2.hkl

e-70-o1126-Isup2.hkl^{(280.4KB, hkl)}

Click here for additional data file.^{(66.7KB, tif)}

Supporting information file. DOI: 10.1107/S160053681402090X/kq2014Isup3.tif

Click here for additional data file.^{(146KB, tif)}

Supporting information file. DOI: 10.1107/S160053681402090X/kq2014Isup4.tif

Click here for additional data file.^{(11.2KB, cml)}

Supporting information file. DOI: 10.1107/S160053681402090X/kq2014Isup5.cml

Click here for additional data file.^{(1.4MB, tif)}

. DOI: 10.1107/S160053681402090X/kq2014fig1.tif

Molecular structure of the title compound. Displacement ellipsoids are presented at the 50% probability level. H atoms are depicted as small spheres of arbitrary radius. Dashed lines indicate the intramolecular N—H⋯O and the intermolecular C—H⋯Cl hydrogen bonds.

Click here for additional data file.^{(2.3MB, tif)}

. DOI: 10.1107/S160053681402090X/kq2014fig2.tif

Crystal packing showing the puckered layers parallel to (100). Dashed lines indicate the intra- and intermolecular hydrogen bonds.

CCDC reference: 1024892

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯Cl1ⁱ	0.84	2.09	2.924 (3)	171
N1—H1A⋯O3	0.92	2.04	2.587 (2)	117
N1—H1B⋯O4ⁱⁱ	0.92	1.87	2.724 (3)	154
C13—H13⋯Cl1	1.00	2.52	3.459 (2)	157
C14—H14B⋯Cl1ⁱⁱⁱ	0.98	2.71	3.593 (2)	150
C18—H18A⋯N3^iv	0.99	2.39	3.367 (4)	168
C29—H29A⋯Cl1^iv	0.98	2.74	3.698 (2)	165

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

Acknowledgments

This work was supported by grants from the Science and Technology Innovation Council of ShenZhen (No. JCYJ20120615172324607).

supplementary crystallographic information

S1. Comment

Moexipril is a nonsulfhydryl containing precursor of the active angiotensin-converting enzyme. It is well known that the polymorphic and pseudo-polymorphic crystals of moexipril show different physico-chemical properties (Klutchko et al., 1986; Suzuki et al., 2010). The crystal structure of the β-form, the monohydrate and the sesquihydrate have been already reported previously (Yamazaki & Suzuki, 1998; Suzuki et al., 2000). In this paper, we report the X-ray crystal structure and stereochemistry of moexipril hydrochloride acetonitrile monosolvate.

S2. Experimental

A solution of 2-[2-[(1-Ethoxycarbonyl-3-phenylpropyl)amino]propanoyl]-6,7-dimethoxy–3,4-dihydro-1H-isoquinoline-3-carboxylic acid in absolute ethanol was treated with hydrochloride in the presence of 5% Pd/C. The resulting mixture was concentrated and stood for 3 h at reduced pressure. The residue obtained was recrystallized from acetonitrile at room temperature to give colourless crystals of I suitable for X-ray diffraction analysis.