Download citation
Download citation
link to html
The title compound, C3H10N+·C5H8NO3·H2O, crystallizes as a salt from water. Inter­molecular N—H...O and O—H...O hydrogen bonds lead to two-dimensional layers. The layers are stacked in the c-axis direction with hydro­phobic inter­actions between the methyl groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050374/hy2088sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050374/hy2088Isup2.hkl
Contains datablock I

CCDC reference: 667388

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.106
  • Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 800 Deg. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C2 ... 1.55 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Chagas disease, which is caused by Trypanosoma cruzi, is an endemic parasitic disease in Latin America, specially in the Southern part of Mexico (Dumonateil, 1999). The Trypanosoma cruzi enzyme desigenated α-hydroxyacid dehydrogenase (HADH) exhibits two molecular forms (I and II). The trypanocidal activity of N-isopropyloxamate (NIPOx) on cultured epimastigotes (in vitro) and marine trypanosomiasis (in vitro) is used in different Trypanosoma cruzi strains. It is an effective and selective inhibitor of HADH-isozyme II (Chena et al., 2005).

It was serendipitously synthesized during a chromatographic partition of cyclenoxamide. The cyclen and diethyl oxalate were added in an equal molar ratio as starting materials to form the cyclenoxamide at room temperature with stirring for 48 h (Bellouard et al., 1999). The reaction stoichiometry should be one to one, so the excess diethyl oxalate was separated by chromatography on silca (CHCl3:isopropylamine, 5:1). The diethyl oxalate reacted with isopropylamine to produce the title compound at room temperature.

The title compound is a salt, consisting of an N-isopropyloxalamate anion, an isopropylaminium cation and a water molecule (Fig. 1). The C1—C2 bond was 1.549 (2) Å which is longer than the typical C(sp2)—C(sp2) bond length. This is most likely due to the stretching by hydrogen bonds at the two sides of the bond. There is a partial double bond between the C2 and N1 [1.326 (2) Å] in the amide group. The cation, anion and water molecule are connected by intermolecular N—H···O and O—H···O hydrogen bonds, as detailed in Table 1 and Figs. 1 and 2. This hydrogen-bonding network is extended in the ab plane to form a layer. The molecular packing consists of the hydrogen-bonding layers alternating with hydrophobic domains along the c direction.

Related literature top

For related literature, see: Chena et al. (2005); Bellouard et al. (1999); Dumonateil (1999).

Experimental top

The title compound was synthesized by reacting excess diethyl oxalate with isopropylamine in chloroform at room temperature. Crystals were obtained by the slow evaporation method. After two weeks colourless plate crystals were deposited. The compound was characterized by proton NMR in deuterated chloroform as follows: 1.12 p.p.m. (6H, d, CH3 for anion); 1.13 p.p.m. (6H, m, CH3 for cation); 3.40 p.p.m. (1H, m, CH for cation); 4.18 p.p.m. (1H, m, CH for anion); 7.35 p.p.m. (1H, d, NH for anion); 7.97(1H, br, NH for cation).

Refinement top

H atoms of CH, CH3 and NH3 groups were positiond geometrically and refined as riding, with C—H = 1.00 Å and Uiso(H) = 1.2Ueq(C) for CH groups, and with C—H = 0.98 and 0.91 Å and Uiso(H) = 1.5Ueq(C,N) for CH3 and NH3 groups. H atoms on N1 and on the water molecule were refined isotropically.

Structure description top

Chagas disease, which is caused by Trypanosoma cruzi, is an endemic parasitic disease in Latin America, specially in the Southern part of Mexico (Dumonateil, 1999). The Trypanosoma cruzi enzyme desigenated α-hydroxyacid dehydrogenase (HADH) exhibits two molecular forms (I and II). The trypanocidal activity of N-isopropyloxamate (NIPOx) on cultured epimastigotes (in vitro) and marine trypanosomiasis (in vitro) is used in different Trypanosoma cruzi strains. It is an effective and selective inhibitor of HADH-isozyme II (Chena et al., 2005).

It was serendipitously synthesized during a chromatographic partition of cyclenoxamide. The cyclen and diethyl oxalate were added in an equal molar ratio as starting materials to form the cyclenoxamide at room temperature with stirring for 48 h (Bellouard et al., 1999). The reaction stoichiometry should be one to one, so the excess diethyl oxalate was separated by chromatography on silca (CHCl3:isopropylamine, 5:1). The diethyl oxalate reacted with isopropylamine to produce the title compound at room temperature.

The title compound is a salt, consisting of an N-isopropyloxalamate anion, an isopropylaminium cation and a water molecule (Fig. 1). The C1—C2 bond was 1.549 (2) Å which is longer than the typical C(sp2)—C(sp2) bond length. This is most likely due to the stretching by hydrogen bonds at the two sides of the bond. There is a partial double bond between the C2 and N1 [1.326 (2) Å] in the amide group. The cation, anion and water molecule are connected by intermolecular N—H···O and O—H···O hydrogen bonds, as detailed in Table 1 and Figs. 1 and 2. This hydrogen-bonding network is extended in the ab plane to form a layer. The molecular packing consists of the hydrogen-bonding layers alternating with hydrophobic domains along the c direction.

For related literature, see: Chena et al. (2005); Bellouard et al. (1999); Dumonateil (1999).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001; Atwood & Barbour, 2003); software used to prepare material for publication: X-SEED (Barbour, 2001; Atwood & Barbour, 2003).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. The red dashed lines represent hydrogen bonds.
[Figure 2] Fig. 2. The molecular packing in the title compound with hydrogen bonds shown as red dashed lines.
Isopropylammonium (isopropylaamino)oxoacetate monohydrate top
Crystal data top
C3H10N+·C5H8NO3·H2OZ = 2
Mr = 208.26F(000) = 228
Triclinic, P1Dx = 1.210 Mg m3
Hall symbol: -P 1Melting point: 56 K
a = 7.172 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.154 (5) ÅCell parameters from 3071 reflections
c = 9.472 (5) Åθ = 2.3–26.5°
α = 104.372 (8)°µ = 0.10 mm1
β = 105.944 (8)°T = 100 K
γ = 94.731 (8)°Plate, colourless
V = 571.6 (5) Å30.38 × 0.19 × 0.08 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2324 independent reflections
Radiation source: fine-focus sealed tube2126 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
φ and ω scansθmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 98
Tmin = 0.962, Tmax = 0.990k = 1111
6062 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H atoms treated by a mixture of independent and constrained refinement
S = 1.16 w = 1/[σ2(Fo2) + (0.0443P)2 + 0.2432P]
where P = (Fo2 + 2Fc2)/3
2324 reflections(Δ/σ)max < 0.001
144 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C3H10N+·C5H8NO3·H2Oγ = 94.731 (8)°
Mr = 208.26V = 571.6 (5) Å3
Triclinic, P1Z = 2
a = 7.172 (4) ÅMo Kα radiation
b = 9.154 (5) ŵ = 0.10 mm1
c = 9.472 (5) ÅT = 100 K
α = 104.372 (8)°0.38 × 0.19 × 0.08 mm
β = 105.944 (8)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2324 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
2126 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.990Rint = 0.023
6062 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.106H atoms treated by a mixture of independent and constrained refinement
S = 1.16Δρmax = 0.40 e Å3
2324 reflectionsΔρmin = 0.21 e Å3
144 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.38400 (15)0.13612 (11)0.08003 (12)0.0186 (2)
N10.36897 (19)0.52457 (13)0.22589 (14)0.0147 (3)
C10.3063 (2)0.25345 (16)0.09391 (15)0.0131 (3)
H10.246 (3)0.512 (2)0.205 (2)0.021 (5)*
O20.12699 (14)0.26313 (11)0.05100 (11)0.0167 (2)
N20.18564 (17)0.14413 (13)0.13379 (13)0.0140 (3)
H2A0.08680.17800.10100.021*
H2B0.27430.20980.13110.021*
H2C0.24630.04960.07170.021*
C20.4503 (2)0.40621 (16)0.17327 (15)0.0131 (3)
O30.62792 (14)0.41075 (11)0.18756 (12)0.0175 (2)
C30.4797 (2)0.67704 (16)0.31163 (17)0.0169 (3)
H30.62320.67110.33690.020*
O40.97028 (16)0.59125 (13)0.18861 (14)0.0211 (3)
C40.4348 (3)0.78700 (18)0.21497 (19)0.0257 (4)
H4A0.47210.75110.12170.039*
H4B0.50930.88880.27350.039*
H4C0.29380.79210.18740.039*
C50.4297 (3)0.73017 (19)0.45995 (18)0.0254 (4)
H5A0.28920.73610.43670.038*
H5B0.50610.83130.51880.038*
H5C0.46160.65740.52000.038*
C60.1027 (2)0.13576 (16)0.29428 (16)0.0161 (3)
H60.21360.10220.33000.019*
C70.0006 (2)0.29326 (17)0.39773 (17)0.0201 (3)
H7A0.11310.32540.36780.030*
H7B0.04360.28970.50420.030*
H7C0.09240.36640.38800.030*
C80.0341 (2)0.01765 (18)0.29648 (18)0.0234 (4)
H8A0.03990.08290.23280.035*
H8B0.09090.01360.40180.035*
H8C0.13970.04600.25630.035*
H90.939 (3)0.622 (3)0.113 (3)0.041 (6)*
H100.859 (3)0.539 (2)0.184 (2)0.033 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0177 (5)0.0116 (5)0.0241 (6)0.0033 (4)0.0055 (4)0.0013 (4)
N10.0106 (6)0.0132 (6)0.0187 (6)0.0023 (5)0.0038 (5)0.0022 (5)
C10.0147 (7)0.0148 (7)0.0106 (6)0.0025 (5)0.0053 (5)0.0032 (5)
O20.0127 (5)0.0166 (5)0.0203 (5)0.0014 (4)0.0049 (4)0.0046 (4)
N20.0122 (6)0.0107 (6)0.0170 (6)0.0016 (4)0.0041 (5)0.0007 (5)
C20.0140 (7)0.0142 (7)0.0122 (6)0.0033 (5)0.0040 (5)0.0050 (5)
O30.0128 (5)0.0138 (5)0.0248 (6)0.0026 (4)0.0067 (4)0.0021 (4)
C30.0131 (7)0.0129 (7)0.0201 (7)0.0006 (5)0.0040 (6)0.0019 (6)
O40.0152 (6)0.0239 (6)0.0258 (6)0.0026 (5)0.0048 (5)0.0116 (5)
C40.0331 (9)0.0181 (8)0.0276 (9)0.0010 (7)0.0137 (7)0.0056 (7)
C50.0281 (9)0.0239 (8)0.0186 (8)0.0001 (7)0.0055 (7)0.0009 (6)
C60.0167 (7)0.0168 (7)0.0148 (7)0.0029 (6)0.0060 (6)0.0031 (5)
C70.0199 (8)0.0185 (8)0.0178 (7)0.0034 (6)0.0037 (6)0.0001 (6)
C80.0288 (9)0.0191 (8)0.0214 (8)0.0092 (6)0.0046 (7)0.0056 (6)
Geometric parameters (Å, º) top
O1—C11.2451 (18)C4—H4A0.9800
N1—C21.3262 (19)C4—H4B0.9800
N1—C31.4623 (19)C4—H4C0.9800
N1—H10.84 (2)C5—H5A0.9800
C1—O21.2554 (18)C5—H5B0.9800
C1—C21.549 (2)C5—H5C0.9800
N2—C61.4963 (19)C6—C71.518 (2)
N2—H2A0.9100C6—C81.519 (2)
N2—H2B0.9100C6—H61.0000
N2—H2C0.9100C7—H7A0.9800
C2—O31.2394 (18)C7—H7B0.9800
C3—C41.518 (2)C7—H7C0.9800
C3—C51.518 (2)C8—H8A0.9800
C3—H31.0000C8—H8B0.9800
O4—H90.81 (2)C8—H8C0.9800
O4—H100.88 (2)
C2—N1—C3123.84 (13)H4A—C4—H4C109.5
C2—N1—H1118.0 (13)H4B—C4—H4C109.5
C3—N1—H1118.1 (13)C3—C5—H5A109.5
O1—C1—O2128.18 (13)C3—C5—H5B109.5
O1—C1—C2115.46 (12)H5A—C5—H5B109.5
O2—C1—C2116.36 (12)C3—C5—H5C109.5
C6—N2—H2A109.5H5A—C5—H5C109.5
C6—N2—H2B109.5H5B—C5—H5C109.5
H2A—N2—H2B109.5N2—C6—C7109.47 (12)
C6—N2—H2C109.5N2—C6—C8109.33 (12)
H2A—N2—H2C109.5C7—C6—C8112.50 (13)
H2B—N2—H2C109.5N2—C6—H6108.5
O3—C2—N1124.74 (13)C7—C6—H6108.5
O3—C2—C1120.31 (12)C8—C6—H6108.5
N1—C2—C1114.92 (12)C6—C7—H7A109.5
N1—C3—C4110.08 (13)C6—C7—H7B109.5
N1—C3—C5109.27 (12)H7A—C7—H7B109.5
C4—C3—C5111.50 (13)C6—C7—H7C109.5
N1—C3—H3108.6H7A—C7—H7C109.5
C4—C3—H3108.6H7B—C7—H7C109.5
C5—C3—H3108.6C6—C8—H8A109.5
H9—O4—H10102 (2)C6—C8—H8B109.5
C3—C4—H4A109.5H8A—C8—H8B109.5
C3—C4—H4B109.5C6—C8—H8C109.5
H4A—C4—H4B109.5H8A—C8—H8C109.5
C3—C4—H4C109.5H8B—C8—H8C109.5
C3—N1—C2—O31.4 (2)O1—C1—C2—N1162.00 (12)
C3—N1—C2—C1176.57 (12)O2—C1—C2—N118.40 (17)
O1—C1—C2—O316.08 (19)C2—N1—C3—C4109.88 (15)
O2—C1—C2—O3163.51 (12)C2—N1—C3—C5127.36 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H9···O2i0.82 (3)2.06 (3)2.864 (2)170 (3)
O4—H10···O30.88 (2)1.96 (2)2.8404 (19)173.5 (19)
N1—H1···O4ii0.84 (2)2.14 (2)2.918 (2)153.7 (17)
N2—H2A···O20.911.892.7957 (19)175
N2—H2B···O3ii0.912.022.8808 (19)157
N2—H2C···O1iii0.911.912.8182 (18)172
Symmetry codes: (i) x+1, y+1, z; (ii) x1, y, z; (iii) x, y, z.

Experimental details

Crystal data
Chemical formulaC3H10N+·C5H8NO3·H2O
Mr208.26
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.172 (4), 9.154 (5), 9.472 (5)
α, β, γ (°)104.372 (8), 105.944 (8), 94.731 (8)
V3)571.6 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.38 × 0.19 × 0.08
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.962, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
6062, 2324, 2126
Rint0.023
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.106, 1.16
No. of reflections2324
No. of parameters144
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.40, 0.21

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001; Atwood & Barbour, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H9···O2i0.82 (3)2.06 (3)2.864 (2)170 (3)
O4—H10···O30.88 (2)1.96 (2)2.8404 (19)173.5 (19)
N1—H1···O4ii0.84 (2)2.14 (2)2.918 (2)153.7 (17)
N2—H2A···O20.911.892.7957 (19)174.5
N2—H2B···O3ii0.912.022.8808 (19)156.6
N2—H2C···O1iii0.911.912.8182 (18)172.4
Symmetry codes: (i) x+1, y+1, z; (ii) x1, y, z; (iii) x, y, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds