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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1766.
Published online 2010 June 23. doi:  10.1107/S1600536810023585
PMCID: PMC3006742

2-Hydroxy-N,N′-diisopropylpropane-1,3-diaminium dichloride

Abstract

In the crystal structure of the title amino alcohol derivative, C9H24N2O2+·2Cl, the cations and anions are linked by inter­molecular O—H(...)Cl and N—H(...)Cl hydrogen bonds into a three-dimensional network.

Related literature

For the applications of amino alcohols and their derivatives in organic synthesis, see: Ellison & Gandhi (2005 [triangle]); Li et al. (2004 [triangle]).

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Object name is e-66-o1766-scheme1.jpg

Experimental

Crystal data

  • C9H24N2O2+·2Cl
  • M r = 247.20
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1766-efi1.jpg
  • a = 6.240 (1) Å
  • b = 10.0081 (14) Å
  • c = 11.3519 (16) Å
  • α = 86.198 (1)°
  • β = 88.052 (2)°
  • γ = 83.308 (1)°
  • V = 702.31 (18) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.44 mm−1
  • T = 298 K
  • 0.50 × 0.45 × 0.44 mm

Data collection

  • Siemens SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.810, T max = 0.830
  • 3684 measured reflections
  • 2448 independent reflections
  • 1999 reflections with I > 2σ(I)
  • R int = 0.016

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.096
  • S = 1.03
  • 2448 reflections
  • 131 parameters
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810023585/rz2467sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023585/rz2467Isup2.hkl

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

Acknowledgments

The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (No. 20572103).

supplementary crystallographic information

Comment

Amino alcohols are important structural elements for the asymmetric catalysis of chiral ligands (Li et al., 2004) as well as of biologically active compounds (Ellison & Gandhi, 2005). In order to develop new applications for amino alcohols and their derivatives, structural modifications of these compounds have been extensively investigated. As a contribution in this filed, we report here the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. Bond lengths and angles in the cation are not unusual. In the crystal packing (Fig. 2), intermolecular O—H···Cl and N—H···Cl hydrogen bonds (Table 1) link molecules into a three-dimensional network.

Experimental

To a solution of isopropamide (24.0 g, 0.4 mol) in acetone (200 ml), epichlorohydrin (9.2 g, 0.1 mol) and K2CO3 (13.8 g, 0.1 mol) were added. The mixture was stirred at room temperature for 8 h, followed by filtration and purification by crystallization from ethyl acetate, giving title compound as colourless single crystals suitable for X-ray analysis.

Refinement

All H atoms were placed geometrically and treated as riding on their parent atoms, with C—H = 0.93–0.98 Å, N—H = 0.90 Å, O—H = 0.82 Å, and with Uiso(H) = 1.2 Ueq(C, N) or 1.5 Ueq(C, O) for methyl and hydroxy H atoms.

Figures

Fig. 1.
The molecular structure of the compound, with atom labels and 50% probability displacement ellipsoids.
Fig. 2.
Crystal packing of the title compound. showing a three-dimensional structure linked by hydrogen bonds (dashed lines).

Crystal data

C9H24N2O2+·2ClZ = 2
Mr = 247.20F(000) = 268
Triclinic, P1Dx = 1.169 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.240 (1) ÅCell parameters from 2066 reflections
b = 10.0081 (14) Åθ = 2.6–27.6°
c = 11.3519 (16) ŵ = 0.44 mm1
α = 86.198 (1)°T = 298 K
β = 88.052 (2)°Block, colourless
γ = 83.308 (1)°0.50 × 0.45 × 0.44 mm
V = 702.31 (18) Å3

Data collection

Siemens SMART CCD area-detector diffractometer2448 independent reflections
Radiation source: fine-focus sealed tube1999 reflections with I > 2σ(I)
graphiteRint = 0.016
phi and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→5
Tmin = 0.810, Tmax = 0.830k = −11→11
3684 measured reflectionsl = −13→10

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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.048P)2 + 0.1942P] where P = (Fo2 + 2Fc2)/3
2448 reflections(Δ/σ)max < 0.001
131 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = −0.23 e Å3

Special details

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)

xyzUiso*/Ueq
Cl10.19859 (8)0.04318 (5)0.75891 (4)0.04461 (17)
Cl20.73770 (9)0.43851 (5)0.17643 (6)0.0585 (2)
N10.0878 (2)0.20330 (14)0.24284 (12)0.0307 (3)
H1A0.03760.12760.22230.037*
H1B−0.00740.27330.21830.037*
N20.4576 (2)0.26100 (14)−0.14466 (12)0.0302 (3)
H2A0.38770.3447−0.15420.036*
H2B0.37420.2041−0.17380.036*
O10.1777 (3)0.09416 (15)0.02964 (12)0.0524 (4)
H10.16970.0850−0.04130.079*
C10.2960 (3)0.21572 (19)0.17837 (16)0.0345 (4)
H1C0.40120.14090.20330.041*
H1D0.35030.29870.19680.041*
C20.2656 (3)0.21601 (17)0.04656 (15)0.0316 (4)
H20.16290.29320.02090.038*
C30.4813 (3)0.22602 (19)−0.01638 (16)0.0355 (4)
H3A0.55340.29420.01820.043*
H3B0.57100.1405−0.00510.043*
C40.0935 (3)0.1991 (2)0.37596 (16)0.0394 (5)
H4−0.05260.18800.40650.047*
C50.2409 (4)0.0782 (2)0.4228 (2)0.0577 (6)
H5A0.2060−0.00120.38800.087*
H5B0.22230.06750.50710.087*
H5C0.38810.09130.40310.087*
C60.1505 (5)0.3315 (2)0.4160 (2)0.0646 (7)
H6A0.29590.34340.39080.097*
H6B0.13850.33090.50060.097*
H6C0.05340.40430.38210.097*
C70.6661 (3)0.25586 (19)−0.21644 (18)0.0385 (4)
H70.74210.1646−0.20690.046*
C80.8085 (3)0.3540 (2)−0.1736 (2)0.0548 (6)
H8A0.73300.4433−0.17900.082*
H8B0.93830.3518−0.22160.082*
H8C0.84450.3291−0.09290.082*
C90.6110 (4)0.2857 (3)−0.34475 (19)0.0578 (6)
H9A0.51860.2223−0.36780.087*
H9B0.74120.2783−0.39260.087*
H9C0.53830.3754−0.35540.087*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0475 (3)0.0492 (3)0.0417 (3)−0.0200 (2)0.0034 (2)−0.0139 (2)
Cl20.0460 (3)0.0349 (3)0.0946 (5)0.0039 (2)−0.0206 (3)−0.0090 (3)
N10.0315 (8)0.0292 (8)0.0316 (8)−0.0018 (6)−0.0026 (6)−0.0046 (6)
N20.0298 (8)0.0272 (7)0.0345 (8)−0.0060 (6)−0.0002 (6)−0.0043 (6)
O10.0714 (10)0.0555 (9)0.0375 (8)−0.0341 (8)0.0079 (7)−0.0129 (7)
C10.0317 (10)0.0387 (10)0.0336 (10)−0.0049 (8)−0.0013 (8)−0.0051 (8)
C20.0328 (10)0.0309 (9)0.0319 (10)−0.0050 (7)−0.0029 (8)−0.0031 (7)
C30.0337 (10)0.0371 (10)0.0358 (10)−0.0044 (8)−0.0030 (8)−0.0010 (8)
C40.0432 (11)0.0474 (11)0.0284 (10)−0.0070 (9)0.0023 (8)−0.0065 (8)
C50.0689 (16)0.0640 (15)0.0370 (12)0.0020 (12)−0.0064 (11)0.0072 (10)
C60.0913 (19)0.0615 (15)0.0450 (13)−0.0129 (13)−0.0062 (13)−0.0226 (11)
C70.0317 (10)0.0351 (10)0.0479 (12)−0.0020 (8)0.0083 (8)−0.0046 (9)
C80.0344 (11)0.0639 (15)0.0677 (15)−0.0160 (10)0.0017 (10)0.0003 (12)
C90.0636 (15)0.0685 (15)0.0427 (13)−0.0159 (12)0.0136 (11)−0.0068 (11)

Geometric parameters (Å, °)

N1—C11.483 (2)C4—C61.513 (3)
N1—C41.510 (2)C4—H40.9800
N1—H1A0.9000C5—H5A0.9600
N1—H1B0.9000C5—H5B0.9600
N2—C31.483 (2)C5—H5C0.9600
N2—C71.509 (2)C6—H6A0.9600
N2—H2A0.9000C6—H6B0.9600
N2—H2B0.9000C6—H6C0.9600
O1—C21.421 (2)C7—C91.510 (3)
O1—H10.8200C7—C81.512 (3)
C1—C21.514 (2)C7—H70.9800
C1—H1C0.9700C8—H8A0.9600
C1—H1D0.9700C8—H8B0.9600
C2—C31.513 (2)C8—H8C0.9600
C2—H20.9800C9—H9A0.9600
C3—H3A0.9700C9—H9B0.9600
C3—H3B0.9700C9—H9C0.9600
C4—C51.511 (3)
C1—N1—C4116.24 (14)N1—C4—H4107.3
C1—N1—H1A108.2C5—C4—H4107.3
C4—N1—H1A108.2C6—C4—H4107.3
C1—N1—H1B108.2C4—C5—H5A109.5
C4—N1—H1B108.2C4—C5—H5B109.5
H1A—N1—H1B107.4H5A—C5—H5B109.5
C3—N2—C7115.27 (14)C4—C5—H5C109.5
C3—N2—H2A108.5H5A—C5—H5C109.5
C7—N2—H2A108.5H5B—C5—H5C109.5
C3—N2—H2B108.5C4—C6—H6A109.5
C7—N2—H2B108.5C4—C6—H6B109.5
H2A—N2—H2B107.5H6A—C6—H6B109.5
C2—O1—H1109.5C4—C6—H6C109.5
N1—C1—C2110.12 (14)H6A—C6—H6C109.5
N1—C1—H1C109.6H6B—C6—H6C109.5
C2—C1—H1C109.6N2—C7—C9108.02 (16)
N1—C1—H1D109.6N2—C7—C8110.37 (16)
C2—C1—H1D109.6C9—C7—C8112.24 (18)
H1C—C1—H1D108.1N2—C7—H7108.7
O1—C2—C3113.58 (15)C9—C7—H7108.7
O1—C2—C1105.22 (14)C8—C7—H7108.7
C3—C2—C1108.81 (14)C7—C8—H8A109.5
O1—C2—H2109.7C7—C8—H8B109.5
C3—C2—H2109.7H8A—C8—H8B109.5
C1—C2—H2109.7C7—C8—H8C109.5
N2—C3—C2112.00 (14)H8A—C8—H8C109.5
N2—C3—H3A109.2H8B—C8—H8C109.5
C2—C3—H3A109.2C7—C9—H9A109.5
N2—C3—H3B109.2C7—C9—H9B109.5
C2—C3—H3B109.2H9A—C9—H9B109.5
H3A—C3—H3B107.9C7—C9—H9C109.5
N1—C4—C5110.60 (16)H9A—C9—H9C109.5
N1—C4—C6110.44 (16)H9B—C9—H9C109.5
C5—C4—C6113.51 (19)
C4—N1—C1—C2178.96 (14)C1—C2—C3—N2−165.75 (14)
N1—C1—C2—O1−56.87 (18)C1—N1—C4—C5−61.5 (2)
N1—C1—C2—C3−178.91 (14)C1—N1—C4—C665.0 (2)
C7—N2—C3—C2−172.65 (14)C3—N2—C7—C9176.59 (16)
O1—C2—C3—N277.43 (19)C3—N2—C7—C8−60.4 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···Cl1i0.822.333.1445 (15)172
N2—H2B···Cl1i0.902.243.1336 (15)173
N2—H2A···Cl2ii0.902.223.1130 (15)172
N1—H1B···Cl2iii0.902.203.0920 (15)174
N1—H1A···Cl1iv0.902.383.2119 (16)154

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2467).

References

  • Ellison, K. E. & Gandhi, G. (2005). Drugs, pp. 787–797. [PubMed]
  • Li, Y., He, B., Qin, B., Feng, X. M. & Zhang, G. L. (2004). J. Org. Chem.69, 7910–7913. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Systems Inc., Madison, Wisconsin, USA.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography