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

Li, A.Z.; Xu, W.J.

doi:10.1107/S160053681402090X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 10| October 2014| Pages o1126-o1127

doi:10.1107/S160053681402090X

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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 and Wen-jie Xu ^a ^*

^aShenzhen Salubris Pharmaceuticals CO., Ltd, Guangdong Shenzhen 361021, People's Republic of China
^*Correspondence e-mail: xjhn0820@163.com

Edited by V. Khrustalev, Russian Academy of Sciences, Russia (Received 14 May 2014; accepted 18 September 2014; online 24 September 2014)

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.

CCDC reference: 1024892

1. 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 ).

2. Experimental

2.1. Crystal data

C₂₇H₃₅N₂O₇⁺·Cl⁻·C₂H₃N
M_r = 576.07
Monoclinic, P 2₁
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 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)

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
Symmetry codes: (i) x, y-1, z; (ii) $[-x+2, y+{\script{1\over 2}}, -z+2]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+2]$ ; (iv) $[-x+2, y-{\script{1\over 2}}, -z+1]$ .

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.

Supporting information

CCDC reference: 1024892

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681402090X/kq2014sup1.cif

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

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

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

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

checkCIF report

Comment top

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.

Related literature top

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).

Experimental top

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.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. 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.
	Fig. 2. Crystal packing showing the puckered layers parallel to (100). Dashed lines indicate the intra- and intermolecular hydrogen bonds.

[(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 top

Crystal data top

C₂₇H₃₅N₂O₇⁺·Cl⁻·C₂H₃N	F(000) = 612
M_r = 576.07	D_x = 1.266 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 6099 reflections
a = 10.9391 (6) Å	θ = 3.3–71.7°
b = 10.4655 (4) Å	µ = 1.52 mm⁻¹
c = 13.3159 (5) Å	T = 103 K
β = 97.419 (4)°	Block, colourless
V = 1511.68 (12) Å³	0.50 × 0.20 × 0.20 mm
Z = 2

Data collection top

Agilent Xcalibur, Eos, Gemini diffractometer	5728 independent reflections
Radiation source: fine-focus sealed tube	5570 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 16.0971 pixels mm^-1	θ_max = 71.8°, θ_min = 3.4°
ω scans	h = −13→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→12
T_min = 0.516, T_max = 0.750	l = −16→16
11078 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0513P)² + 0.3525P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
5728 reflections	Δρ_max = 0.55 e Å⁻³
367 parameters	Δρ_min = −0.34 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2620 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.000 (10)

Crystal data top

C₂₇H₃₅N₂O₇⁺·Cl⁻·C₂H₃N	V = 1511.68 (12) Å³
M_r = 576.07	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 10.9391 (6) Å	µ = 1.52 mm⁻¹
b = 10.4655 (4) Å	T = 103 K
c = 13.3159 (5) Å	0.50 × 0.20 × 0.20 mm
β = 97.419 (4)°

Data collection top

Agilent Xcalibur, Eos, Gemini diffractometer	5728 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	5570 reflections with I > 2σ(I)
T_min = 0.516, T_max = 0.750	R_int = 0.021
11078 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.087	Δρ_max = 0.55 e Å⁻³
S = 1.03	Δρ_min = −0.34 e Å⁻³
5728 reflections	Absolute structure: Flack (1983), 2620 Friedel pairs
367 parameters	Absolute structure parameter: 0.000 (10)
1 restraint

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.93335 (4)	0.48179 (4)	0.82049 (3)	0.02184 (10)
O6	0.52273 (13)	0.26128 (14)	0.40381 (11)	0.0274 (3)
O5	0.79427 (13)	−0.28384 (13)	0.76776 (12)	0.0286 (3)
H5	0.8374	−0.3472	0.7887	0.043*
O3	0.81278 (12)	−0.00568 (13)	0.94514 (9)	0.0204 (3)
O4	0.96943 (12)	−0.17651 (13)	0.81353 (10)	0.0214 (3)
O2	0.73833 (13)	0.45383 (13)	1.15813 (10)	0.0240 (3)
C22	0.77885 (16)	0.30103 (17)	0.60435 (13)	0.0174 (3)
H22	0.8293	0.3680	0.6349	0.021*
O1	0.73521 (14)	0.24231 (14)	1.19090 (11)	0.0285 (3)
O7	0.65710 (12)	0.44801 (12)	0.48979 (10)	0.0229 (3)
N2	0.85280 (14)	0.05279 (14)	0.78967 (11)	0.0173 (3)
C25	0.62888 (17)	0.10402 (18)	0.51823 (14)	0.0204 (4)
H25	0.5763	0.0373	0.4902	0.024*
C17	0.86058 (16)	−0.17996 (17)	0.78125 (12)	0.0170 (3)
C23	0.68475 (16)	0.32815 (18)	0.52690 (13)	0.0185 (3)
C15	0.86015 (16)	0.06883 (17)	0.88977 (13)	0.0168 (3)
C26	0.7471 (2)	0.54471 (19)	0.51712 (15)	0.0278 (4)
H26A	0.7196	0.6252	0.4840	0.042*
H26B	0.8257	0.5190	0.4954	0.042*
H26C	0.7578	0.5564	0.5908	0.042*
N1	0.87847 (13)	0.20668 (14)	1.03592 (10)	0.0154 (3)
H1A	0.8400	0.1330	1.0528	0.018*
H1B	0.9429	0.2227	1.0859	0.018*
C20	0.79909 (16)	0.17574 (18)	0.63698 (12)	0.0172 (3)
C6	0.50803 (18)	0.34869 (19)	0.75184 (15)	0.0242 (4)
H6	0.5901	0.3387	0.7369	0.029*
C8	0.67413 (17)	0.28867 (19)	0.95447 (14)	0.0209 (4)
H8A	0.7007	0.2557	0.8911	0.025*
H8B	0.6235	0.2219	0.9818	0.025*
C24	0.61083 (17)	0.22814 (19)	0.48234 (14)	0.0202 (4)
C13	0.92855 (16)	0.18674 (17)	0.93702 (12)	0.0160 (3)
H13	0.9074	0.2624	0.8923	0.019*
C21	0.90294 (16)	0.13908 (17)	0.71794 (13)	0.0174 (3)
H21A	0.9693	0.0957	0.6870	0.021*
H21B	0.9379	0.2164	0.7536	0.021*
C14	1.06858 (16)	0.17006 (19)	0.95410 (13)	0.0207 (4)
H14A	1.0983	0.1501	0.8896	0.031*
H14B	1.0900	0.1001	1.0020	0.031*
H14C	1.1071	0.2493	0.9817	0.031*
C9	0.78851 (16)	0.31546 (17)	1.03144 (13)	0.0171 (3)
H9	0.8295	0.3954	1.0118	0.021*
C18	0.75488 (17)	−0.05633 (18)	0.63247 (13)	0.0202 (4)
H18A	0.8264	−0.0883	0.6013	0.024*
H18B	0.6840	−0.1132	0.6111	0.024*
C16	0.78556 (16)	−0.06097 (17)	0.74921 (13)	0.0170 (3)
H16	0.7063	−0.0656	0.7790	0.020*
C12	0.5522 (2)	0.4949 (2)	1.23442 (16)	0.0331 (5)
H12A	0.5295	0.5680	1.1899	0.050*
H12B	0.5200	0.5075	1.2990	0.050*
H12C	0.5170	0.4166	1.2021	0.050*
C2	0.36654 (19)	0.3986 (2)	0.86908 (16)	0.0288 (4)
H2	0.3510	0.4224	0.9351	0.035*
C10	0.75218 (16)	0.33115 (19)	1.13720 (14)	0.0203 (4)
C19	0.72420 (17)	0.07729 (18)	0.59540 (13)	0.0185 (4)
C28	0.9733 (2)	0.2135 (3)	0.4377 (2)	0.0452 (6)
C29	0.9077 (2)	0.1088 (2)	0.38715 (17)	0.0317 (5)
H29A	0.9422	0.0895	0.3245	0.048*
H29B	0.8205	0.1315	0.3709	0.048*
H29C	0.9155	0.0335	0.4313	0.048*
C27	0.49224 (18)	0.1638 (2)	0.32940 (14)	0.0260 (4)
H27A	0.4375	0.1993	0.2721	0.039*
H27B	0.4506	0.0933	0.3595	0.039*
H27C	0.5678	0.1322	0.3056	0.039*
C1	0.48732 (18)	0.38403 (19)	0.84900 (15)	0.0235 (4)
C11	0.69039 (18)	0.4832 (2)	1.25307 (14)	0.0283 (4)
H11A	0.7266	0.5643	1.2812	0.034*
H11B	0.7138	0.4145	1.3030	0.034*
C3	0.26836 (19)	0.3788 (2)	0.79368 (18)	0.0326 (5)
H3	0.1862	0.3895	0.8082	0.039*
C5	0.41007 (19)	0.3281 (2)	0.67694 (15)	0.0276 (4)
H5A	0.4253	0.3031	0.6111	0.033*
C4	0.28987 (19)	0.3435 (2)	0.69729 (17)	0.0303 (4)
H4	0.2228	0.3300	0.6455	0.036*
N3	1.0276 (3)	0.2938 (3)	0.4810 (3)	0.0866 (12)
C7	0.59528 (19)	0.40899 (19)	0.93067 (15)	0.0268 (4)
H7A	0.5636	0.4384	0.9931	0.032*
H7B	0.6473	0.4778	0.9079	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0299 (2)	0.01598 (18)	0.01952 (19)	0.00160 (16)	0.00259 (15)	0.00102 (15)
O6	0.0268 (7)	0.0263 (7)	0.0257 (7)	0.0052 (6)	−0.0092 (6)	0.0006 (6)
O5	0.0232 (7)	0.0160 (7)	0.0432 (9)	−0.0014 (5)	−0.0095 (6)	0.0032 (6)
O3	0.0274 (6)	0.0178 (6)	0.0161 (5)	−0.0040 (5)	0.0039 (5)	0.0010 (5)
O4	0.0188 (6)	0.0201 (6)	0.0235 (7)	0.0006 (5)	−0.0033 (5)	0.0023 (5)
O2	0.0287 (7)	0.0232 (7)	0.0213 (6)	−0.0008 (5)	0.0084 (5)	−0.0059 (5)
C22	0.0185 (8)	0.0208 (9)	0.0135 (8)	−0.0032 (7)	0.0040 (6)	−0.0023 (6)
O1	0.0358 (8)	0.0269 (7)	0.0250 (7)	0.0003 (6)	0.0121 (6)	0.0033 (6)
O7	0.0258 (7)	0.0203 (7)	0.0211 (6)	0.0029 (5)	−0.0020 (5)	0.0027 (5)
N2	0.0198 (7)	0.0162 (7)	0.0150 (7)	−0.0004 (6)	−0.0006 (6)	−0.0003 (6)
C25	0.0200 (9)	0.0220 (9)	0.0184 (8)	−0.0002 (7)	−0.0005 (7)	−0.0030 (7)
C17	0.0204 (8)	0.0181 (9)	0.0117 (8)	0.0003 (7)	−0.0007 (6)	−0.0003 (6)
C23	0.0204 (8)	0.0206 (9)	0.0156 (8)	0.0040 (7)	0.0068 (6)	0.0016 (7)
C15	0.0179 (8)	0.0163 (8)	0.0157 (8)	0.0040 (6)	0.0009 (6)	0.0003 (6)
C26	0.0367 (11)	0.0193 (10)	0.0260 (10)	0.0000 (8)	−0.0019 (8)	0.0028 (8)
N1	0.0168 (7)	0.0175 (7)	0.0116 (6)	0.0005 (5)	0.0006 (5)	−0.0003 (5)
C20	0.0172 (8)	0.0235 (9)	0.0112 (7)	0.0007 (7)	0.0037 (6)	0.0000 (7)
C6	0.0213 (9)	0.0263 (10)	0.0253 (10)	0.0046 (7)	0.0037 (7)	0.0044 (8)
C8	0.0204 (9)	0.0230 (9)	0.0187 (9)	0.0022 (7)	−0.0002 (7)	−0.0019 (7)
C24	0.0169 (8)	0.0270 (10)	0.0162 (8)	0.0036 (7)	−0.0003 (7)	0.0006 (7)
C13	0.0197 (8)	0.0167 (8)	0.0116 (7)	0.0018 (7)	0.0017 (6)	0.0007 (6)
C21	0.0173 (8)	0.0206 (9)	0.0142 (8)	−0.0013 (6)	0.0015 (6)	0.0003 (6)
C14	0.0190 (9)	0.0254 (10)	0.0179 (8)	0.0000 (7)	0.0026 (7)	−0.0005 (7)
C9	0.0189 (8)	0.0155 (8)	0.0172 (8)	0.0010 (7)	0.0030 (6)	−0.0025 (6)
C18	0.0243 (9)	0.0191 (9)	0.0160 (8)	0.0011 (7)	−0.0015 (7)	−0.0027 (7)
C16	0.0188 (8)	0.0170 (8)	0.0151 (8)	−0.0006 (7)	0.0010 (6)	−0.0008 (6)
C12	0.0349 (11)	0.0371 (12)	0.0291 (10)	0.0074 (10)	0.0111 (8)	−0.0039 (9)
C2	0.0284 (10)	0.0317 (11)	0.0274 (10)	0.0094 (8)	0.0079 (8)	0.0054 (8)
C10	0.0158 (8)	0.0251 (9)	0.0203 (9)	−0.0016 (7)	0.0032 (7)	−0.0035 (7)
C19	0.0200 (9)	0.0210 (9)	0.0146 (8)	0.0016 (7)	0.0029 (7)	−0.0018 (7)
C28	0.0409 (13)	0.0531 (16)	0.0477 (14)	−0.0144 (12)	0.0293 (12)	−0.0160 (12)
C29	0.0277 (10)	0.0404 (12)	0.0278 (10)	−0.0020 (9)	0.0064 (8)	−0.0019 (9)
C27	0.0229 (9)	0.0316 (10)	0.0207 (9)	−0.0006 (8)	−0.0071 (7)	0.0004 (8)
C1	0.0251 (9)	0.0203 (9)	0.0248 (9)	0.0070 (7)	0.0020 (8)	0.0032 (7)
C11	0.0311 (10)	0.0326 (10)	0.0222 (9)	−0.0015 (9)	0.0077 (7)	−0.0106 (9)
C3	0.0211 (10)	0.0326 (11)	0.0443 (13)	0.0066 (8)	0.0054 (9)	0.0093 (9)
C5	0.0323 (10)	0.0259 (10)	0.0239 (10)	0.0029 (8)	0.0013 (8)	0.0012 (8)
C4	0.0261 (10)	0.0230 (10)	0.0388 (12)	0.0017 (8)	−0.0069 (8)	0.0042 (8)
N3	0.081 (2)	0.088 (2)	0.105 (2)	−0.0498 (18)	0.0661 (19)	−0.059 (2)
C7	0.0289 (10)	0.0260 (11)	0.0243 (9)	0.0101 (8)	−0.0004 (8)	−0.0035 (7)

Geometric parameters (Å, º) top

O6—C24	1.372 (2)	C13—C14	1.529 (2)
O6—C27	1.431 (2)	C13—H13	1.0000
O5—C17	1.306 (2)	C21—H21A	0.9900
O5—H5	0.8400	C21—H21B	0.9900
O3—C15	1.232 (2)	C14—H14A	0.9800
O4—C17	1.213 (2)	C14—H14B	0.9800
O2—C10	1.327 (2)	C14—H14C	0.9800
O2—C11	1.462 (2)	C9—C10	1.521 (2)
C22—C23	1.389 (2)	C9—H9	1.0000
C22—C20	1.390 (3)	C18—C19	1.506 (3)
C22—H22	0.9500	C18—C16	1.548 (2)
O1—C10	1.202 (2)	C18—H18A	0.9900
O7—C23	1.368 (2)	C18—H18B	0.9900
O7—C26	1.426 (2)	C16—H16	1.0000
N2—C15	1.336 (2)	C12—C11	1.505 (3)
N2—C16	1.465 (2)	C12—H12A	0.9800
N2—C21	1.471 (2)	C12—H12B	0.9800
C25—C24	1.389 (3)	C12—H12C	0.9800
C25—C19	1.395 (3)	C2—C3	1.388 (3)
C25—H25	0.9500	C2—C1	1.390 (3)
C17—C16	1.522 (2)	C2—H2	0.9500
C23—C24	1.406 (3)	C28—N3	1.141 (4)
C15—C13	1.535 (2)	C28—C29	1.430 (3)
C26—H26A	0.9800	C29—H29A	0.9800
C26—H26B	0.9800	C29—H29B	0.9800
C26—H26C	0.9800	C29—H29C	0.9800
N1—C9	1.501 (2)	C27—H27A	0.9800
N1—C13	1.505 (2)	C27—H27B	0.9800
N1—H1A	0.9200	C27—H27C	0.9800
N1—H1B	0.9200	C1—C7	1.521 (3)
C20—C19	1.386 (3)	C11—H11A	0.9900
C20—C21	1.511 (2)	C11—H11B	0.9900
C6—C5	1.383 (3)	C3—C4	1.385 (3)
C6—C1	1.392 (3)	C3—H3	0.9500
C6—H6	0.9500	C5—C4	1.386 (3)
C8—C7	1.536 (2)	C5—H5A	0.9500
C8—C9	1.537 (2)	C4—H4	0.9500
C8—H8A	0.9900	C7—H7A	0.9900
C8—H8B	0.9900	C7—H7B	0.9900

C24—O6—C27	115.19 (15)	C10—C9—C8	110.46 (14)
C17—O5—H5	109.5	N1—C9—H9	109.4
C10—O2—C11	116.64 (15)	C10—C9—H9	109.4
C23—C22—C20	119.84 (16)	C8—C9—H9	109.4
C23—C22—H22	120.1	C19—C18—C16	111.62 (14)
C20—C22—H22	120.1	C19—C18—H18A	109.3
C23—O7—C26	116.47 (14)	C16—C18—H18A	109.3
C15—N2—C16	115.59 (14)	C19—C18—H18B	109.3
C15—N2—C21	126.25 (15)	C16—C18—H18B	109.3
C16—N2—C21	118.14 (14)	H18A—C18—H18B	108.0
C24—C25—C19	120.04 (17)	N2—C16—C17	109.56 (14)
C24—C25—H25	120.0	N2—C16—C18	112.16 (14)
C19—C25—H25	120.0	C17—C16—C18	110.26 (14)
O4—C17—O5	125.15 (16)	N2—C16—H16	108.2
O4—C17—C16	122.96 (16)	C17—C16—H16	108.2
O5—C17—C16	111.88 (14)	C18—C16—H16	108.2
O7—C23—C22	124.31 (17)	C11—C12—H12A	109.5
O7—C23—C24	116.23 (16)	C11—C12—H12B	109.5
C22—C23—C24	119.46 (17)	H12A—C12—H12B	109.5
O3—C15—N2	122.80 (17)	C11—C12—H12C	109.5
O3—C15—C13	118.93 (15)	H12A—C12—H12C	109.5
N2—C15—C13	118.26 (15)	H12B—C12—H12C	109.5
O7—C26—H26A	109.5	C3—C2—C1	120.7 (2)
O7—C26—H26B	109.5	C3—C2—H2	119.7
H26A—C26—H26B	109.5	C1—C2—H2	119.7
O7—C26—H26C	109.5	O1—C10—O2	126.37 (17)
H26A—C26—H26C	109.5	O1—C10—C9	123.12 (18)
H26B—C26—H26C	109.5	O2—C10—C9	110.47 (16)
C9—N1—C13	112.41 (13)	C20—C19—C25	119.49 (17)
C9—N1—H1A	109.1	C20—C19—C18	117.64 (16)
C13—N1—H1A	109.1	C25—C19—C18	122.78 (16)
C9—N1—H1B	109.1	N3—C28—C29	177.4 (4)
C13—N1—H1B	109.1	C28—C29—H29A	109.5
H1A—N1—H1B	107.9	C28—C29—H29B	109.5
C19—C20—C22	120.94 (16)	H29A—C29—H29B	109.5
C19—C20—C21	116.57 (16)	C28—C29—H29C	109.5
C22—C20—C21	122.49 (16)	H29A—C29—H29C	109.5
C5—C6—C1	120.51 (18)	H29B—C29—H29C	109.5
C5—C6—H6	119.7	O6—C27—H27A	109.5
C1—C6—H6	119.7	O6—C27—H27B	109.5
C7—C8—C9	112.03 (15)	H27A—C27—H27B	109.5
C7—C8—H8A	109.2	O6—C27—H27C	109.5
C9—C8—H8A	109.2	H27A—C27—H27C	109.5
C7—C8—H8B	109.2	H27B—C27—H27C	109.5
C9—C8—H8B	109.2	C2—C1—C6	118.74 (18)
H8A—C8—H8B	107.9	C2—C1—C7	120.87 (18)
O6—C24—C25	123.58 (17)	C6—C1—C7	120.37 (17)
O6—C24—C23	116.26 (16)	O2—C11—C12	109.82 (15)
C25—C24—C23	120.15 (16)	O2—C11—H11A	109.7
N1—C13—C14	110.89 (13)	C12—C11—H11A	109.7
N1—C13—C15	104.89 (14)	O2—C11—H11B	109.7
C14—C13—C15	113.26 (15)	C12—C11—H11B	109.7
N1—C13—H13	109.2	H11A—C11—H11B	108.2
C14—C13—H13	109.2	C4—C3—C2	120.15 (19)
C15—C13—H13	109.2	C4—C3—H3	119.9
N2—C21—C20	108.06 (14)	C2—C3—H3	119.9
N2—C21—H21A	110.1	C6—C5—C4	120.46 (19)
C20—C21—H21A	110.1	C6—C5—H5A	119.8
N2—C21—H21B	110.1	C4—C5—H5A	119.8
C20—C21—H21B	110.1	C3—C4—C5	119.44 (19)
H21A—C21—H21B	108.4	C3—C4—H4	120.3
C13—C14—H14A	109.5	C5—C4—H4	120.3
C13—C14—H14B	109.5	C1—C7—C8	111.73 (16)
H14A—C14—H14B	109.5	C1—C7—H7A	109.3
C13—C14—H14C	109.5	C8—C7—H7A	109.3
H14A—C14—H14C	109.5	C1—C7—H7B	109.3
H14B—C14—H14C	109.5	C8—C7—H7B	109.3
N1—C9—C10	107.06 (14)	H7A—C7—H7B	107.9
N1—C9—C8	111.17 (14)

C26—O7—C23—C22	14.3 (2)	C15—N2—C16—C18	166.61 (15)
C26—O7—C23—C24	−166.07 (16)	C21—N2—C16—C18	−12.1 (2)
C20—C22—C23—O7	179.68 (16)	O4—C17—C16—N2	−16.0 (2)
C20—C22—C23—C24	0.0 (3)	O5—C17—C16—N2	165.23 (15)
C16—N2—C15—O3	−0.8 (2)	O4—C17—C16—C18	107.90 (19)
C21—N2—C15—O3	177.83 (16)	O5—C17—C16—C18	−70.85 (19)
C16—N2—C15—C13	−179.54 (14)	C19—C18—C16—N2	−36.4 (2)
C21—N2—C15—C13	−0.9 (3)	C19—C18—C16—C17	−158.82 (15)
C23—C22—C20—C19	−2.0 (3)	C11—O2—C10—O1	−4.1 (3)
C23—C22—C20—C21	177.53 (15)	C11—O2—C10—C9	173.57 (14)
C27—O6—C24—C25	−29.9 (3)	N1—C9—C10—O1	−39.3 (2)
C27—O6—C24—C23	150.20 (17)	C8—C9—C10—O1	81.9 (2)
C19—C25—C24—O6	177.08 (17)	N1—C9—C10—O2	142.99 (15)
C19—C25—C24—C23	−3.0 (3)	C8—C9—C10—O2	−95.82 (17)
O7—C23—C24—O6	2.7 (2)	C22—C20—C19—C25	1.4 (3)
C22—C23—C24—O6	−177.65 (16)	C21—C20—C19—C25	−178.13 (16)
O7—C23—C24—C25	−177.23 (16)	C22—C20—C19—C18	178.01 (16)
C22—C23—C24—C25	2.5 (3)	C21—C20—C19—C18	−1.5 (2)
C9—N1—C13—C14	133.60 (15)	C24—C25—C19—C20	1.1 (3)
C9—N1—C13—C15	−103.80 (15)	C24—C25—C19—C18	−175.32 (17)
O3—C15—C13—N1	−21.2 (2)	C16—C18—C19—C20	44.4 (2)
N2—C15—C13—N1	157.68 (15)	C16—C18—C19—C25	−139.15 (18)
O3—C15—C13—C14	99.90 (19)	C3—C2—C1—C6	−0.2 (3)
N2—C15—C13—C14	−81.27 (19)	C3—C2—C1—C7	178.4 (2)
C15—N2—C21—C20	−124.98 (18)	C5—C6—C1—C2	−0.3 (3)
C16—N2—C21—C20	53.6 (2)	C5—C6—C1—C7	−178.89 (19)
C19—C20—C21—N2	−46.4 (2)	C10—O2—C11—C12	−92.1 (2)
C22—C20—C21—N2	134.08 (17)	C1—C2—C3—C4	0.3 (3)
C13—N1—C9—C10	−176.13 (14)	C1—C6—C5—C4	0.7 (3)
C13—N1—C9—C8	63.13 (18)	C2—C3—C4—C5	0.1 (3)
C7—C8—C9—N1	−167.02 (15)	C6—C5—C4—C3	−0.6 (3)
C7—C8—C9—C10	74.3 (2)	C2—C1—C7—C8	118.7 (2)
C15—N2—C16—C17	−70.60 (18)	C6—C1—C7—C8	−62.7 (2)
C21—N2—C16—C17	110.70 (16)	C9—C8—C7—C1	175.96 (16)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, y−1, z; (ii) −x+2, y+1/2, −z+2; (iii) −x+2, y−1/2, −z+2; (iv) −x+2, y−1/2, −z+1.

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, y−1, z; (ii) −x+2, y+1/2, −z+2; (iii) −x+2, y−1/2, −z+2; (iv) −x+2, y−1/2, −z+1.

Acknowledgements

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

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 70| Part 10| October 2014| Pages o1126-o1127

doi:10.1107/S160053681402090X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

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