2-Hydroxy-N,N'-diisopropylpropane-1,3-diaminium dichloride.

In the crystal structure of the title amino alcohol derivative, C(9)H(24)N(2)O(2+)·2Cl(-), the cations and anions are linked by inter-molecular 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 ▶); Li et al. (2004 ▶).

Experimental

Crystal data

C9H24N2O2+·2Cl−

M = 247.20

Triclinic,

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 ▶) 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 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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.

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

C9H24N2O2+·2Cl−	Z = 2
Mr = 247.20	F(000) = 268
Triclinic, P1	Dx = 1.169 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.240 (1) Å	Cell parameters from 2066 reflections
b = 10.0081 (14) Å	θ = 2.6–27.6°
c = 11.3519 (16) Å	µ = 0.44 mm−1
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

Siemens SMART CCD area-detector diffractometer	2448 independent reflections
Radiation source: fine-focus sealed tube	1999 reflections with I > 2σ(I)
graphite	Rint = 0.016
phi and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→5
Tmin = 0.810, Tmax = 0.830	k = −11→11
3684 measured reflections	l = −13→10

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-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 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.19859 (8)	0.04318 (5)	0.75891 (4)	0.04461 (17)
Cl2	0.73770 (9)	0.43851 (5)	0.17643 (6)	0.0585 (2)
N1	0.0878 (2)	0.20330 (14)	0.24284 (12)	0.0307 (3)
H1A	0.0376	0.1276	0.2223	0.037*
H1B	−0.0074	0.2733	0.2183	0.037*
N2	0.4576 (2)	0.26100 (14)	−0.14466 (12)	0.0302 (3)
H2A	0.3877	0.3447	−0.1542	0.036*
H2B	0.3742	0.2041	−0.1738	0.036*
O1	0.1777 (3)	0.09416 (15)	0.02964 (12)	0.0524 (4)
H1	0.1697	0.0850	−0.0413	0.079*
C1	0.2960 (3)	0.21572 (19)	0.17837 (16)	0.0345 (4)
H1C	0.4012	0.1409	0.2033	0.041*
H1D	0.3503	0.2987	0.1968	0.041*
C2	0.2656 (3)	0.21601 (17)	0.04656 (15)	0.0316 (4)
H2	0.1629	0.2932	0.0209	0.038*
C3	0.4813 (3)	0.22602 (19)	−0.01638 (16)	0.0355 (4)
H3A	0.5534	0.2942	0.0182	0.043*
H3B	0.5710	0.1405	−0.0051	0.043*
C4	0.0935 (3)	0.1991 (2)	0.37596 (16)	0.0394 (5)
H4	−0.0526	0.1880	0.4065	0.047*
C5	0.2409 (4)	0.0782 (2)	0.4228 (2)	0.0577 (6)
H5A	0.2060	−0.0012	0.3880	0.087*
H5B	0.2223	0.0675	0.5071	0.087*
H5C	0.3881	0.0913	0.4031	0.087*
C6	0.1505 (5)	0.3315 (2)	0.4160 (2)	0.0646 (7)
H6A	0.2959	0.3434	0.3908	0.097*
H6B	0.1385	0.3309	0.5006	0.097*
H6C	0.0534	0.4043	0.3821	0.097*
C7	0.6661 (3)	0.25586 (19)	−0.21644 (18)	0.0385 (4)
H7	0.7421	0.1646	−0.2069	0.046*
C8	0.8085 (3)	0.3540 (2)	−0.1736 (2)	0.0548 (6)
H8A	0.7330	0.4433	−0.1790	0.082*
H8B	0.9383	0.3518	−0.2216	0.082*
H8C	0.8445	0.3291	−0.0929	0.082*
C9	0.6110 (4)	0.2857 (3)	−0.34475 (19)	0.0578 (6)
H9A	0.5186	0.2223	−0.3678	0.087*
H9B	0.7412	0.2783	−0.3926	0.087*
H9C	0.5383	0.3754	−0.3554	0.087*

	U11	U22	U33	U12	U13	U23
Cl1	0.0475 (3)	0.0492 (3)	0.0417 (3)	−0.0200 (2)	0.0034 (2)	−0.0139 (2)
Cl2	0.0460 (3)	0.0349 (3)	0.0946 (5)	0.0039 (2)	−0.0206 (3)	−0.0090 (3)
N1	0.0315 (8)	0.0292 (8)	0.0316 (8)	−0.0018 (6)	−0.0026 (6)	−0.0046 (6)
N2	0.0298 (8)	0.0272 (7)	0.0345 (8)	−0.0060 (6)	−0.0002 (6)	−0.0043 (6)
O1	0.0714 (10)	0.0555 (9)	0.0375 (8)	−0.0341 (8)	0.0079 (7)	−0.0129 (7)
C1	0.0317 (10)	0.0387 (10)	0.0336 (10)	−0.0049 (8)	−0.0013 (8)	−0.0051 (8)
C2	0.0328 (10)	0.0309 (9)	0.0319 (10)	−0.0050 (7)	−0.0029 (8)	−0.0031 (7)
C3	0.0337 (10)	0.0371 (10)	0.0358 (10)	−0.0044 (8)	−0.0030 (8)	−0.0010 (8)
C4	0.0432 (11)	0.0474 (11)	0.0284 (10)	−0.0070 (9)	0.0023 (8)	−0.0065 (8)
C5	0.0689 (16)	0.0640 (15)	0.0370 (12)	0.0020 (12)	−0.0064 (11)	0.0072 (10)
C6	0.0913 (19)	0.0615 (15)	0.0450 (13)	−0.0129 (13)	−0.0062 (13)	−0.0226 (11)
C7	0.0317 (10)	0.0351 (10)	0.0479 (12)	−0.0020 (8)	0.0083 (8)	−0.0046 (9)
C8	0.0344 (11)	0.0639 (15)	0.0677 (15)	−0.0160 (10)	0.0017 (10)	0.0003 (12)
C9	0.0636 (15)	0.0685 (15)	0.0427 (13)	−0.0159 (12)	0.0136 (11)	−0.0068 (11)

N1—C1	1.483 (2)	C4—C6	1.513 (3)
N1—C4	1.510 (2)	C4—H4	0.9800
N1—H1A	0.9000	C5—H5A	0.9600
N1—H1B	0.9000	C5—H5B	0.9600
N2—C3	1.483 (2)	C5—H5C	0.9600
N2—C7	1.509 (2)	C6—H6A	0.9600
N2—H2A	0.9000	C6—H6B	0.9600
N2—H2B	0.9000	C6—H6C	0.9600
O1—C2	1.421 (2)	C7—C9	1.510 (3)
O1—H1	0.8200	C7—C8	1.512 (3)
C1—C2	1.514 (2)	C7—H7	0.9800
C1—H1C	0.9700	C8—H8A	0.9600
C1—H1D	0.9700	C8—H8B	0.9600
C2—C3	1.513 (2)	C8—H8C	0.9600
C2—H2	0.9800	C9—H9A	0.9600
C3—H3A	0.9700	C9—H9B	0.9600
C3—H3B	0.9700	C9—H9C	0.9600
C4—C5	1.511 (3)
C1—N1—C4	116.24 (14)	N1—C4—H4	107.3
C1—N1—H1A	108.2	C5—C4—H4	107.3
C4—N1—H1A	108.2	C6—C4—H4	107.3
C1—N1—H1B	108.2	C4—C5—H5A	109.5
C4—N1—H1B	108.2	C4—C5—H5B	109.5
H1A—N1—H1B	107.4	H5A—C5—H5B	109.5
C3—N2—C7	115.27 (14)	C4—C5—H5C	109.5
C3—N2—H2A	108.5	H5A—C5—H5C	109.5
C7—N2—H2A	108.5	H5B—C5—H5C	109.5
C3—N2—H2B	108.5	C4—C6—H6A	109.5
C7—N2—H2B	108.5	C4—C6—H6B	109.5
H2A—N2—H2B	107.5	H6A—C6—H6B	109.5
C2—O1—H1	109.5	C4—C6—H6C	109.5
N1—C1—C2	110.12 (14)	H6A—C6—H6C	109.5
N1—C1—H1C	109.6	H6B—C6—H6C	109.5
C2—C1—H1C	109.6	N2—C7—C9	108.02 (16)
N1—C1—H1D	109.6	N2—C7—C8	110.37 (16)
C2—C1—H1D	109.6	C9—C7—C8	112.24 (18)
H1C—C1—H1D	108.1	N2—C7—H7	108.7
O1—C2—C3	113.58 (15)	C9—C7—H7	108.7
O1—C2—C1	105.22 (14)	C8—C7—H7	108.7
C3—C2—C1	108.81 (14)	C7—C8—H8A	109.5
O1—C2—H2	109.7	C7—C8—H8B	109.5
C3—C2—H2	109.7	H8A—C8—H8B	109.5
C1—C2—H2	109.7	C7—C8—H8C	109.5
N2—C3—C2	112.00 (14)	H8A—C8—H8C	109.5
N2—C3—H3A	109.2	H8B—C8—H8C	109.5
C2—C3—H3A	109.2	C7—C9—H9A	109.5
N2—C3—H3B	109.2	C7—C9—H9B	109.5
C2—C3—H3B	109.2	H9A—C9—H9B	109.5
H3A—C3—H3B	107.9	C7—C9—H9C	109.5
N1—C4—C5	110.60 (16)	H9A—C9—H9C	109.5
N1—C4—C6	110.44 (16)	H9B—C9—H9C	109.5
C5—C4—C6	113.51 (19)
C4—N1—C1—C2	178.96 (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—C6	65.0 (2)
C7—N2—C3—C2	−172.65 (14)	C3—N2—C7—C9	176.59 (16)
O1—C2—C3—N2	77.43 (19)	C3—N2—C7—C8	−60.4 (2)

D—H···A	D—H	H···A	D···A	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

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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) ; (ii) ; (iii) ; (iv) .