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

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ISSN: 2056-9890

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

aDepartment of Quality Detection and Management, Zhengzhou College of Animal Husbandry Engineering, Zhengzhou 450011, People's Republic of China
*Correspondence e-mail: muzhi527@163.com

(Received 11 June 2010; accepted 17 June 2010; online 23 June 2010)

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[Ellison, K. E. & Gandhi, G. (2005). Drugs, pp. 787-797.]); Li et al. (2004[Li, Y., He, B., Qin, B., Feng, X. M. & Zhang, G. L. (2004). J. Org. Chem. 69, 7910-7913.]).

[Scheme 1]

Experimental

Crystal data
  • C9H24N2O2+·2Cl

  • Mr = 247.20

  • Triclinic, [P \overline 1]

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.810, Tmax = 0.830

  • 3684 measured reflections

  • 2448 independent reflections

  • 1999 reflections with I > 2σ(I)

  • Rint = 0.016

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯Cl1i 0.82 2.33 3.1445 (15) 172
N2—H2B⋯Cl1i 0.90 2.24 3.1336 (15) 173
N2—H2A⋯Cl2ii 0.90 2.22 3.1130 (15) 172
N1—H1B⋯Cl2iii 0.90 2.20 3.0920 (15) 174
N1—H1A⋯Cl1iv 0.90 2.38 3.2119 (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.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of the compound, with atom labels and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Crystal packing of the title compound. showing a three-dimensional structure linked by hydrogen bonds (dashed lines).
2-Hydroxy-N,N'-diisopropylpropane-1,3-diaminium dichloride top
Crystal data top
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 top
Siemens SMART CCD area-detector
diffractometer
2448 independent reflections
Radiation source: fine-focus sealed tube1999 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
phi and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 75
Tmin = 0.810, Tmax = 0.830k = 1111
3684 measured reflectionsl = 1310
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.03 w = 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
Crystal data top
C9H24N2O2+·2Clγ = 83.308 (1)°
Mr = 247.20V = 702.31 (18) Å3
Triclinic, P1Z = 2
a = 6.240 (1) ÅMo Kα radiation
b = 10.0081 (14) ŵ = 0.44 mm1
c = 11.3519 (16) ÅT = 298 K
α = 86.198 (1)°0.50 × 0.45 × 0.44 mm
β = 88.052 (2)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
2448 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1999 reflections with I > 2σ(I)
Tmin = 0.810, Tmax = 0.830Rint = 0.016
3684 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.096H-atom parameters constrained
S = 1.03Δρmax = 0.25 e Å3
2448 reflectionsΔρmin = 0.23 e Å3
131 parameters
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
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*
H1B0.00740.27330.21830.037*
N20.4576 (2)0.26100 (14)0.14466 (12)0.0302 (3)
H2A0.38770.34470.15420.036*
H2B0.37420.20410.17380.036*
O10.1777 (3)0.09416 (15)0.02964 (12)0.0524 (4)
H10.16970.08500.04130.079*
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*
H3B0.57100.14050.00510.043*
C40.0935 (3)0.1991 (2)0.37596 (16)0.0394 (5)
H40.05260.18800.40650.047*
C50.2409 (4)0.0782 (2)0.4228 (2)0.0577 (6)
H5A0.20600.00120.38800.087*
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)
H70.74210.16460.20690.046*
C80.8085 (3)0.3540 (2)0.1736 (2)0.0548 (6)
H8A0.73300.44330.17900.082*
H8B0.93830.35180.22160.082*
H8C0.84450.32910.09290.082*
C90.6110 (4)0.2857 (3)0.34475 (19)0.0578 (6)
H9A0.51860.22230.36780.087*
H9B0.74120.27830.39260.087*
H9C0.53830.37540.35540.087*
Atomic displacement parameters (Å2) top
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, º) top
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—N2165.75 (14)
N1—C1—C2—O156.87 (18)C1—N1—C4—C561.5 (2)
N1—C1—C2—C3178.91 (14)C1—N1—C4—C665.0 (2)
C7—N2—C3—C2172.65 (14)C3—N2—C7—C9176.59 (16)
O1—C2—C3—N277.43 (19)C3—N2—C7—C860.4 (2)
Hydrogen-bond geometry (Å, º) top
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, z1; (ii) x+1, y+1, z; (iii) x1, y, z; (iv) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC9H24N2O2+·2Cl
Mr247.20
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)6.240 (1), 10.0081 (14), 11.3519 (16)
α, β, γ (°)86.198 (1), 88.052 (2), 83.308 (1)
V3)702.31 (18)
Z2
Radiation typeMo Kα
µ (mm1)0.44
Crystal size (mm)0.50 × 0.45 × 0.44
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.810, 0.830
No. of measured, independent and
observed [I > 2σ(I)] reflections
3684, 2448, 1999
Rint0.016
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.096, 1.03
No. of reflections2448
No. of parameters131
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.23

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···Cl1i0.822.333.1445 (15)171.5
N2—H2B···Cl1i0.902.243.1336 (15)173.2
N2—H2A···Cl2ii0.902.223.1130 (15)171.7
N1—H1B···Cl2iii0.902.203.0920 (15)173.5
N1—H1A···Cl1iv0.902.383.2119 (16)154.0
Symmetry codes: (i) x, y, z1; (ii) x+1, y+1, z; (iii) x1, y, z; (iv) x, y, z+1.
 

Acknowledgements

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

References

First citationEllison, K. E. & Gandhi, G. (2005). Drugs, pp. 787–797.  Web of Science CrossRef Google Scholar
First citationLi, Y., He, B., Qin, B., Feng, X. M. & Zhang, G. L. (2004). J. Org. Chem. 69, 7910–7913.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems Inc., Madison, Wisconsin, USA.  Google Scholar

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ISSN: 2056-9890
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