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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1364.
Published online 2010 May 15. doi:  10.1107/S1600536810017484
PMCID: PMC2979568

Amiloride hydro­chloride methanol disolvate

Abstract

In the crystal of the title compound [systematic name: 2-(3,5-diamino-6-chloro­pyrazin-2-ylcarbon­yl)guanidinium chloride methanol disolvate], C6H9ClN7O+·Cl·2CH3OH , the components are connected by N—H(...)N, N—H(...)Cl, N—H(...)O, O—H(...)Cl and O—H(...)O hydrogen bonds into a three-dimensional network. The dihedral angle between the aromatic ring and the guanidine residue is 6.0 (2)°.

Related literature

For other salts of amiloride, see: Pretscher et al. (2001 [triangle]); Zeslawska et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1364-scheme1.jpg

Experimental

Crystal data

  • C6H9ClN7O+·Cl·2CH4O
  • M r = 330.19
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1364-efi1.jpg
  • a = 5.9473 (5) Å
  • b = 16.7278 (17) Å
  • c = 14.7784 (15) Å
  • β = 90.080 (8)°
  • V = 1470.2 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.46 mm−1
  • T = 173 K
  • 0.30 × 0.25 × 0.20 mm

Data collection

  • Stoe IPDS II two-circle diffractometer
  • Absorption correction: multi-scan (MULABS; Spek, 2009 [triangle]; Blessing, 1995 [triangle]) T min = 0.874, T max = 0.914
  • 19184 measured reflections
  • 2739 independent reflections
  • 1852 reflections with I > 2σ(I)
  • R int = 0.071

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.080
  • S = 0.96
  • 2739 reflections
  • 212 parameters
  • 9 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 [triangle]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810017484/ng2772sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017484/ng2772Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Experimental

Crystals of the title structure were obtained by recrystallization of amiloride hydrochloride (100 mg) from a methanol (3 g) solution.

Refinement

H atoms bonded to O and C were geometrically positioned and refined using a riding model with fixed individual displacement parameters [U(H) = 1.5 Ueq(C,O)] using a riding model with C—H = 0.98Å and O—H = 0.84 Å, respectively. The methyl and hydroxyl groups were allowed to rotate but not to tip. H atoms bonded to N were refined with a distance restraint of 0.88 (1)Å and with U(H) = 1.2 Ueq(N).

Figures

Fig. 1.
Perspective view of the asymmetric unit of the title compound. Displacement ellipsoids are at the 50° probability level.

Crystal data

C6H9ClN7O+·Cl·2CH4OF(000) = 688
Mr = 330.19Dx = 1.492 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 11166 reflections
a = 5.9473 (5) Åθ = 3.7–25.7°
b = 16.7278 (17) ŵ = 0.46 mm1
c = 14.7784 (15) ÅT = 173 K
β = 90.080 (8)°Block, colourless
V = 1470.2 (2) Å30.30 × 0.25 × 0.20 mm
Z = 4

Data collection

Stoe IPDS II two-circle diffractometer2739 independent reflections
Radiation source: fine-focus sealed tube1852 reflections with I > 2σ(I)
graphiteRint = 0.071
ω scansθmax = 25.6°, θmin = 3.6°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)h = −7→7
Tmin = 0.874, Tmax = 0.914k = −20→20
19184 measured reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 0.96w = 1/[σ2(Fo2) + (0.0253P)2] where P = (Fo2 + 2Fc2)/3
2739 reflections(Δ/σ)max < 0.001
212 parametersΔρmax = 0.22 e Å3
9 restraintsΔρmin = −0.25 e Å3

Special details

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

xyzUiso*/Ueq
N10.4136 (4)0.07364 (14)0.32999 (16)0.0187 (6)
C20.5851 (5)0.02607 (17)0.32413 (18)0.0179 (6)
Cl20.62266 (14)−0.02883 (5)0.22493 (5)0.0315 (2)
C30.7485 (5)0.01732 (16)0.39568 (19)0.0182 (6)
N310.9232 (4)−0.03176 (16)0.38692 (17)0.0241 (6)
H31A1.006 (5)−0.0400 (18)0.4354 (14)0.029*
H31B0.939 (5)−0.0621 (16)0.3394 (14)0.029*
N40.7256 (4)0.06106 (13)0.47133 (16)0.0179 (5)
C50.5473 (5)0.11111 (16)0.47856 (19)0.0173 (6)
N510.5303 (5)0.15414 (15)0.55477 (18)0.0256 (6)
H51A0.624 (4)0.1497 (18)0.6007 (15)0.031*
H51B0.410 (3)0.1839 (16)0.561 (2)0.031*
C60.3874 (5)0.11725 (17)0.40695 (19)0.0168 (6)
C110.1930 (5)0.17089 (18)0.4093 (2)0.0202 (7)
O110.1433 (4)0.21444 (12)0.47391 (14)0.0249 (5)
N120.0642 (4)0.16832 (14)0.33015 (15)0.0173 (5)
H120.110 (5)0.1370 (14)0.2874 (15)0.021*
C13−0.1158 (5)0.21632 (17)0.3097 (2)0.0196 (7)
N14−0.2054 (4)0.20867 (16)0.22820 (18)0.0250 (6)
H14A−0.326 (3)0.2377 (16)0.218 (2)0.030*
H14B−0.134 (5)0.1739 (15)0.1935 (18)0.030*
N15−0.1985 (4)0.26602 (16)0.37008 (18)0.0250 (6)
H15A−0.310 (4)0.2979 (16)0.355 (2)0.030*
H15B−0.141 (5)0.2664 (19)0.4246 (11)0.030*
Cl10.36907 (12)0.32420 (4)0.23835 (5)0.02329 (18)
O1M0.4195 (4)0.44145 (13)0.39875 (15)0.0335 (6)
H1M0.40010.41390.35190.050*
C1M0.2507 (6)0.4216 (2)0.4641 (2)0.0355 (8)
H1M10.26370.36500.48020.053*
H1M20.10150.43180.43840.053*
H1M30.27160.45450.51830.053*
O2M0.4108 (4)0.59993 (13)0.35076 (15)0.0315 (6)
H2M0.41960.55040.35920.047*
C2MA0.2302 (6)0.6318 (2)0.4037 (2)0.0370 (9)
H2M10.08830.60710.38480.056*
H2M20.22140.68980.39450.056*
H2M30.25730.62050.46780.056*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0148 (14)0.0184 (13)0.0229 (14)−0.0003 (11)−0.0025 (10)0.0018 (11)
C20.0171 (15)0.0209 (15)0.0157 (14)−0.0018 (13)−0.0030 (12)0.0000 (12)
Cl20.0278 (5)0.0391 (5)0.0276 (4)0.0122 (4)−0.0061 (3)−0.0114 (4)
C30.0142 (15)0.0149 (15)0.0254 (16)−0.0011 (13)0.0002 (12)0.0037 (13)
N310.0209 (14)0.0244 (15)0.0268 (15)0.0082 (12)−0.0059 (12)−0.0050 (12)
N40.0133 (13)0.0146 (12)0.0258 (14)0.0018 (10)−0.0036 (10)0.0012 (10)
C50.0172 (16)0.0129 (14)0.0220 (16)−0.0037 (12)−0.0017 (12)0.0012 (12)
N510.0250 (16)0.0269 (15)0.0250 (15)0.0067 (12)−0.0070 (12)−0.0061 (12)
C60.0125 (15)0.0141 (14)0.0238 (16)−0.0012 (12)−0.0014 (12)−0.0002 (12)
C110.0186 (16)0.0162 (15)0.0257 (16)−0.0046 (13)−0.0006 (13)0.0037 (14)
O110.0265 (12)0.0212 (11)0.0268 (12)0.0062 (9)−0.0021 (9)−0.0042 (9)
N120.0174 (13)0.0166 (13)0.0180 (13)0.0043 (11)−0.0024 (10)−0.0011 (10)
C130.0141 (15)0.0156 (15)0.0290 (17)−0.0004 (12)0.0001 (13)0.0027 (13)
N140.0197 (15)0.0272 (15)0.0280 (16)0.0083 (11)−0.0061 (12)0.0000 (12)
N150.0197 (15)0.0263 (15)0.0290 (15)0.0103 (12)−0.0039 (12)−0.0018 (12)
Cl10.0196 (4)0.0206 (4)0.0296 (4)0.0024 (3)−0.0022 (3)0.0006 (3)
O1M0.0372 (14)0.0317 (14)0.0317 (13)−0.0091 (11)0.0034 (11)−0.0026 (10)
C1M0.040 (2)0.0347 (19)0.0318 (19)−0.0092 (17)−0.0015 (16)0.0054 (16)
O2M0.0344 (14)0.0271 (13)0.0328 (13)−0.0055 (11)−0.0006 (11)0.0064 (11)
C2MA0.039 (2)0.033 (2)0.039 (2)−0.0027 (17)0.0032 (17)0.0001 (16)

Geometric parameters (Å, °)

N1—C21.297 (4)N12—H120.866 (10)
N1—C61.360 (4)C13—N151.316 (4)
C2—C31.443 (4)C13—N141.322 (4)
C2—Cl21.745 (3)N14—H14A0.880 (10)
C3—N311.331 (4)N14—H14B0.884 (10)
C3—N41.343 (4)N15—H15A0.880 (10)
N31—H31A0.880 (10)N15—H15B0.876 (10)
N31—H31B0.872 (10)O1M—C1M1.432 (4)
N4—C51.355 (4)O1M—H1M0.8400
C5—N511.341 (4)C1M—H1M10.9800
C5—C61.426 (4)C1M—H1M20.9800
N51—H51A0.879 (10)C1M—H1M30.9800
N51—H51B0.878 (10)O2M—C2MA1.433 (4)
C6—C111.464 (4)O2M—H2M0.8400
C11—O111.238 (3)C2MA—H2M10.9800
C11—N121.398 (4)C2MA—H2M20.9800
N12—C131.371 (4)C2MA—H2M30.9800
C2—N1—C6118.4 (2)C11—N12—H12117 (2)
N1—C2—C3122.9 (3)N15—C13—N14121.9 (3)
N1—C2—Cl2118.7 (2)N15—C13—N12120.8 (3)
C3—C2—Cl2118.4 (2)N14—C13—N12117.2 (3)
N31—C3—N4119.8 (3)C13—N14—H14A116 (2)
N31—C3—C2121.1 (3)C13—N14—H14B114 (2)
N4—C3—C2119.1 (3)H14A—N14—H14B131 (3)
C3—N31—H31A117 (2)C13—N15—H15A119 (2)
C3—N31—H31B122 (2)C13—N15—H15B119 (2)
H31A—N31—H31B120 (3)H15A—N15—H15B122 (3)
C3—N4—C5118.8 (2)C1M—O1M—H1M109.5
N51—C5—N4117.2 (3)O1M—C1M—H1M1109.5
N51—C5—C6122.3 (3)O1M—C1M—H1M2109.5
N4—C5—C6120.5 (3)H1M1—C1M—H1M2109.5
C5—N51—H51A124 (2)O1M—C1M—H1M3109.5
C5—N51—H51B117 (2)H1M1—C1M—H1M3109.5
H51A—N51—H51B119 (3)H1M2—C1M—H1M3109.5
N1—C6—C5120.3 (3)C2MA—O2M—H2M109.5
N1—C6—C11116.1 (2)O2M—C2MA—H2M1109.5
C5—C6—C11123.6 (3)O2M—C2MA—H2M2109.5
O11—C11—N12122.2 (3)H2M1—C2MA—H2M2109.5
O11—C11—C6124.6 (3)O2M—C2MA—H2M3109.5
N12—C11—C6113.2 (3)H2M1—C2MA—H2M3109.5
C13—N12—C11126.4 (2)H2M2—C2MA—H2M3109.5
C13—N12—H12116 (2)
C6—N1—C2—C30.1 (4)N51—C5—C6—N1178.7 (3)
C6—N1—C2—Cl2−178.9 (2)N4—C5—C6—N1−0.8 (4)
N1—C2—C3—N31−179.6 (3)N51—C5—C6—C110.6 (4)
Cl2—C2—C3—N31−0.5 (4)N4—C5—C6—C11−178.9 (3)
N1—C2—C3—N4−1.1 (4)N1—C6—C11—O11179.6 (3)
Cl2—C2—C3—N4178.0 (2)C5—C6—C11—O11−2.2 (4)
N31—C3—N4—C5179.5 (3)N1—C6—C11—N12−0.1 (4)
C2—C3—N4—C51.1 (4)C5—C6—C11—N12178.1 (3)
C3—N4—C5—N51−179.7 (2)O11—C11—N12—C136.0 (4)
C3—N4—C5—C6−0.2 (4)C6—C11—N12—C13−174.3 (3)
C2—N1—C6—C50.8 (4)C11—N12—C13—N15−6.9 (4)
C2—N1—C6—C11179.0 (3)C11—N12—C13—N14175.0 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N31—H31A···N4i0.88 (1)2.14 (1)2.996 (3)165 (3)
N31—H31B···Cl1ii0.87 (1)2.50 (2)3.281 (3)150 (3)
N51—H51A···Cl1iii0.88 (1)2.54 (1)3.396 (3)165 (3)
N51—H51B···O110.88 (1)2.11 (2)2.781 (3)133 (3)
N12—H12···O2Miv0.87 (1)2.14 (2)2.912 (3)149 (3)
N14—H14A···Cl1v0.88 (1)2.34 (1)3.188 (3)162 (3)
N14—H14B···O2Miv0.88 (1)1.93 (2)2.783 (3)162 (3)
N15—H15A···Cl1v0.88 (1)2.61 (2)3.367 (3)145 (3)
N15—H15B···O110.88 (1)2.03 (3)2.688 (3)131 (3)
O1M—H1M···Cl10.842.263.091 (2)171
O2M—H2M···O1M0.841.912.745 (3)170

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+3/2, y−1/2, −z+1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x+1/2, y−1/2, −z+1/2; (v) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2772).

References

  • Blessing, R. H. (1995). Acta Cryst. A51, 33–38. [PubMed]
  • Pretscher, A., Brisander, M., Bauer-Brandl, A. & Hansen, L. K. (2001). Acta Cryst. C57, 1217–1219. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Stoe & Cie (2001). X-AREA Stoe & Cie, Darmstadt, Germany.
  • Zeslawska, E., Oleksyn, B. & Stadnicka, K. (2004). Struct. Chem.15, 567–571.

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