Disordered structure of propane-1,2-diaminium dichloride.

In the title compound, C(3)H(12)N(2) (2+)·2Cl(-), the cations are disordered over two well resolved positions in a 0.525 (13):0.475 (13) ratio. The disorder involves two C atoms which assume positions that make an almost mirror-sym-metrical system. Similar disorder is observed both at room temperature and at 120 (1) K. The conformation of the NCCN chain in both components is close to trans (the torsion angles ca ±170°), while that of CCCN chain is close to gauche (±50°). In the crystal, a network of relatively strong N-H⋯Cl hydrogen bonds connects the cations and anions into one-cation-deep layers parallel to (001); there are R(2) (4)(8) and R(2) (4)(11) ring motifs within the plane. The planes are only loosely connected by van der Waals contacts and electrostatic inter-actions between cations and anions.

Related literature

For general literature on polyamines, see, for example: Hosseinkhani et al. (2004 ▶); Pospieszna-Markiewicz et al. (2006 ▶, 2007 ▶); Ziebarth & Wang (2009 ▶); Itaka et al. (2010 ▶). For the crystal structures of simple salts of propane-1,2-diaminium, see: Aghabozorg et al. (2008 ▶); Gerrard & Weller (2002 ▶); Lee & Harrison (2003 ▶); Todd & Harrison (2005 ▶).

Experimental

Crystal data

C3H12N2 2+·2Cl−

M = 147.05

Orthorhombic,

a = 10.985 (3) Å

b = 7.079 (2) Å

c = 9.698 (2) Å

V = 754.1 (3) Å3

Z = 4

Cu Kα radiation

μ = 6.95 mm−1

T = 120 K

0.25 × 0.1 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.640, T max = 1.000

2817 measured reflections

1306 independent reflections

1265 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.098

S = 1.13

1306 reflections

86 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.34 e Å−3

Absolute structure: Flack (1983 ▶), 473 Friedel pairs

Flack parameter: 0.09 (3)

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811001036/cv5036sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001036/cv5036Isup2.hkl

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

C3H12N22+·2Cl−	F(000) = 312
Mr = 147.05	Dx = 1.295 Mg m−3
Orthorhombic, Pna21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2n	Cell parameters from 2191 reflections
a = 10.985 (3) Å	θ = 4.0–75.5°
b = 7.079 (2) Å	µ = 6.95 mm−1
c = 9.698 (2) Å	T = 120 K
V = 754.1 (3) Å3	Block, colourless
Z = 4	0.25 × 0.1 × 0.05 mm

Oxford Diffraction Xcalibur Eos diffractometer	1306 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1265 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 16.1544 pixels mm-1	θmax = 75.7°, θmin = 7.4°
ω scans	h = −12→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −8→8
Tmin = 0.640, Tmax = 1.000	l = −11→12
2817 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0669P)2 + 0.1755P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max = 0.001
1306 reflections	Δρmax = 0.33 e Å−3
86 parameters	Δρmin = −0.34 e Å−3
1 restraint	Absolute structure: Flack (1983), 473 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.09 (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	Occ. (<1)
N1	0.2839 (2)	0.7068 (3)	0.5952 (3)	0.0290 (5)
H1A	0.2462	0.7953	0.5422	0.043*	0.525 (13)
H1B	0.2269	0.6348	0.6386	0.043*	0.525 (13)
H1C	0.3313	0.7653	0.6592	0.043*	0.525 (13)
H1D	0.2547	0.8030	0.5424	0.043*	0.475 (13)
H1E	0.2252	0.6685	0.6552	0.043*	0.475 (13)
H1F	0.3501	0.7474	0.6432	0.043*	0.475 (13)
C2	0.3589 (9)	0.5771 (12)	0.5034 (11)	0.027 (2)	0.525 (13)
H2	0.4390	0.6396	0.4858	0.032*	0.525 (13)
C21	0.2954 (9)	0.5541 (8)	0.3682 (7)	0.034 (2)	0.525 (13)
H21A	0.2133	0.5043	0.3838	0.051*	0.525 (13)
H21B	0.3412	0.4660	0.3101	0.051*	0.525 (13)
H21C	0.2899	0.6769	0.3219	0.051*	0.525 (13)
C2A	0.3142 (10)	0.5396 (15)	0.5026 (12)	0.027 (2)	0.475 (13)
H2A	0.2358	0.4795	0.4737	0.032*	0.475 (13)
C21A	0.3753 (8)	0.6147 (11)	0.3760 (8)	0.035 (2)	0.475 (13)
H21D	0.4024	0.5091	0.3184	0.052*	0.475 (13)
H21E	0.4458	0.6913	0.4028	0.052*	0.475 (13)
H21F	0.3178	0.6929	0.3241	0.052*	0.475 (13)
C3	0.3821 (3)	0.4007 (4)	0.5893 (4)	0.0328 (7)
H3A	0.3024	0.3566	0.6246	0.039*	0.525 (13)
H3B	0.4341	0.4308	0.6697	0.039*	0.525 (13)
H3C	0.4454	0.4649	0.6448	0.039*	0.475 (13)
H3D	0.3222	0.3452	0.6540	0.039*	0.475 (13)
N4	0.4396 (2)	0.2468 (3)	0.5090 (3)	0.0253 (5)
H4A	0.5061	0.2925	0.4640	0.038*
H4B	0.3854	0.2007	0.4466	0.038*
H4C	0.4629	0.1526	0.5672	0.038*
Cl1	0.18604 (6)	0.05885 (8)	0.42805 (6)	0.0279 (2)
Cl2	0.52155 (6)	0.91848 (8)	0.70308 (9)	0.0328 (2)

	U11	U22	U33	U12	U13	U23
N1	0.0357 (13)	0.0183 (12)	0.0329 (12)	0.0056 (9)	0.0017 (10)	−0.0040 (9)
C2	0.036 (5)	0.009 (4)	0.035 (4)	0.005 (3)	−0.003 (4)	0.000 (3)
C21	0.053 (5)	0.015 (3)	0.034 (4)	0.007 (3)	−0.014 (3)	0.002 (2)
C2A	0.033 (5)	0.014 (5)	0.033 (4)	0.004 (4)	0.009 (4)	−0.002 (3)
C21A	0.049 (5)	0.022 (3)	0.033 (3)	0.015 (3)	0.008 (3)	0.011 (3)
C3	0.0530 (18)	0.0185 (13)	0.0269 (14)	0.0108 (12)	0.0001 (13)	0.0005 (10)
N4	0.0319 (12)	0.0141 (11)	0.0298 (12)	0.0028 (9)	−0.0006 (9)	−0.0012 (8)
Cl1	0.0323 (3)	0.0199 (3)	0.0314 (3)	0.0026 (2)	−0.0011 (3)	−0.0003 (2)
Cl2	0.0350 (4)	0.0252 (3)	0.0383 (4)	−0.0001 (2)	−0.0050 (3)	0.0103 (3)

N1—C2	1.522 (10)	C2A—C3	1.493 (12)
N1—C2A	1.523 (10)	C2A—C21A	1.496 (14)
N1—H1A	0.9100	C2A—H2A	1.0000
N1—H1B	0.9100	C21A—H21D	0.9800
N1—H1C	0.9101	C21A—H21E	0.9800
N1—H1D	0.9101	C21A—H21F	0.9800
N1—H1E	0.9100	C3—N4	1.481 (4)
N1—H1F	0.9100	C3—H3A	0.9900
C2—C21	1.495 (13)	C3—H3B	0.9900
C2—C3	1.523 (10)	C3—H3C	0.9900
C2—H2	1.0000	C3—H3D	0.9899
C21—H21A	0.9800	N4—H4A	0.9100
C21—H21B	0.9800	N4—H4B	0.9100
C21—H21C	0.9800	N4—H4C	0.9100
C2—N1—H1A	109.3	C2A—C21A—H21D	109.5
C2A—N1—H1A	107.5	C2A—C21A—H21E	109.5
C2—N1—H1B	107.7	H21D—C21A—H21E	109.5
C2A—N1—H1B	89.3	C2A—C21A—H21F	109.5
H1A—N1—H1B	109.5	H21D—C21A—H21F	109.5
C2—N1—H1C	111.3	H21E—C21A—H21F	109.5
C2A—N1—H1C	129.1	N4—C3—C2A	113.7 (5)
H1A—N1—H1C	109.5	N4—C3—C2	112.8 (4)
H1B—N1—H1C	109.5	N4—C3—H3A	109.1
C2A—N1—H1D	109.0	C2A—C3—H3A	87.7
C2A—N1—H1E	107.5	C2—C3—H3A	107.4
H1D—N1—H1E	109.5	N4—C3—H3B	109.0
C2A—N1—H1F	111.9	C2A—C3—H3B	126.1
H1D—N1—H1F	109.5	C2—C3—H3B	110.5
H1E—N1—H1F	109.5	H3A—C3—H3B	107.8
C21—C2—N1	109.0 (7)	N4—C3—H3C	108.8
C21—C2—C3	118.0 (7)	C2A—C3—H3C	110.7
N1—C2—C3	105.4 (7)	N4—C3—H3D	109.0
C21—C2—H2	108.0	C2A—C3—H3D	106.6
N1—C2—H2	108.0	H3C—C3—H3D	107.7
C3—C2—H2	108.0	C3—N4—H4A	109.5
C3—C2A—C21A	118.2 (8)	C3—N4—H4B	109.5
C3—C2A—N1	106.8 (7)	H4A—N4—H4B	109.5
C21A—C2A—N1	107.8 (8)	C3—N4—H4C	109.5
C3—C2A—H2A	107.9	H4A—N4—H4C	109.5
C21A—C2A—H2A	107.9	H4B—N4—H4C	109.5
N1—C2A—H2A	107.9
C2A—N1—C2—C21	54.9 (18)	C21A—C2A—C3—C2	45.2 (16)
C2A—N1—C2—C3	−72.6 (19)	N1—C2A—C3—C2	−76.3 (19)
C2—N1—C2A—C3	78.5 (19)	C21—C2—C3—N4	50.0 (10)
C2—N1—C2A—C21A	−49.4 (17)	N1—C2—C3—N4	172.0 (4)
C21A—C2A—C3—N4	−47.0 (11)	C21—C2—C3—C2A	−47.0 (17)
N1—C2A—C3—N4	−168.5 (4)	N1—C2—C3—C2A	74.9 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···Cl1i	0.91	2.25	3.161 (3)	175
N1—H1E···Cl2ii	0.91	2.37	3.192 (3)	151
N1—H1F···Cl2	0.91	2.31	3.187 (3)	161
N4—H4B···Cl1	0.91	2.42	3.186 (3)	142
N4—H4A···Cl1iii	0.91	2.27	3.136 (3)	160
N4—H4C···Cl2iv	0.91	2.21	3.123 (2)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯Cl1i	0.91	2.25	3.161 (3)	175
N1—H1E⋯Cl2ii	0.91	2.37	3.192 (3)	151
N1—H1F⋯Cl2	0.91	2.31	3.187 (3)	161
N4—H4B⋯Cl1	0.91	2.42	3.186 (3)	142
N4—H4A⋯Cl1iii	0.91	2.27	3.136 (3)	160
N4—H4C⋯Cl2iv	0.91	2.21	3.123 (2)	178

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .