Redetermination of trans-cyclo-hexane-1,4-diammonium dichloride.

A redetermination of the crystal structure of the title compound, C(6)H(16)N(2) (2+)·2Cl(-), was undertaken. All atomic coordinates including those of the H atoms were refined freely. The cation is located on a centre of symmetry. Important for the crystal structure are wavy hydrogen-bonded layers that are formed by ammonium groups and chloride anions, giving hydrogen-bonded rings.

Related literature

For previous structure determinations, see: Dunitz & Strickler (1965 ▶, 1966 ▶). For the isostructural cyclo­hexane-1,4-diammonium dibromide, see: Rademeyer (2006 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶); Rademeyer (2006 ▶).

Experimental

Crystal data

C6H16N2 2+·2Cl−

M = 187.11

Monoclinic,

a = 5.2550 (11) Å

b = 14.890 (3) Å

c = 6.3604 (12) Å

β = 99.824 (18)°

V = 490.39 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.60 mm−1

T = 293 (2) K

0.30 × 0.24 × 0.20 mm

Data collection

Stoe STADI CCD diffractometer

Absorption correction: none

13502 measured reflections

1766 independent reflections

1562 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.072

S = 1.03

1766 reflections

79 parameters

All H-atom parameters refined

Δρmax = 0.41 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis CCD (Kuma Diffraction, 2000 ▶); cell refinement: CrysAlis RED (Kuma Diffraction, 2000 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: DIAMOND (Brandenburg, 2001 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807064793/gd2030sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064793/gd2030Isup2.hkl

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

C6H16N22+·2Cl–	F000 = 200
Mr = 187.11	Dx = 1.267 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
a = 5.2550 (11) Å	Cell parameters from 1610 reflections
b = 14.890 (3) Å	θ = 4.8–17.4º
c = 6.3604 (12) Å	µ = 0.60 mm−1
β = 99.824 (18)º	T = 293 (2) K
V = 490.39 (16) Å3	Block, colourless
Z = 2	0.30 × 0.24 × 0.20 mm

Stoe STADI CCD diffractometer	1562 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
Monochromator: graphite	θmax = 32.5º
T = 293(2) K	θmin = 4.3º
ω scans	h = −7→7
Absorption correction: none	k = −22→22
13502 measured reflections	l = −8→9
1766 independent reflections

Refinement on F2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.038	w = 1/[σ2(Fo2) + 0.3P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.072	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.41 e Å−3
1766 reflections	Δρmin = −0.28 e Å−3
79 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.174 (6)
Secondary atom site location: difference Fourier map

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	0.46825 (6)	0.15413 (2)	0.46296 (5)	0.03915 (12)
N1	0.5260 (2)	0.34260 (8)	0.24820 (19)	0.0338 (2)
H1	0.522 (3)	0.2870 (13)	0.316 (3)	0.051 (5)*
H2	0.642 (4)	0.3377 (12)	0.168 (3)	0.057 (5)*
H3	0.377 (4)	0.3498 (12)	0.163 (3)	0.050 (5)*
C1	0.6023 (3)	0.50463 (8)	0.3001 (2)	0.0335 (3)
H11	0.448 (3)	0.5150 (11)	0.198 (3)	0.041 (4)*
H12	0.738 (4)	0.5022 (11)	0.221 (3)	0.043 (4)*
C2	0.5751 (2)	0.41590 (8)	0.41008 (18)	0.0281 (2)
H21	0.726 (3)	0.4018 (10)	0.503 (2)	0.029 (3)*
C3	0.3565 (3)	0.41864 (9)	0.5386 (2)	0.0358 (3)
H31	0.203 (3)	0.4276 (11)	0.445 (3)	0.042 (4)*
H32	0.355 (3)	0.3590 (11)	0.613 (3)	0.044 (4)*

	U11	U22	U33	U12	U13	U23
Cl1	0.03850 (18)	0.03987 (18)	0.04168 (19)	−0.00250 (12)	0.01427 (13)	0.00190 (13)
N1	0.0361 (5)	0.0330 (5)	0.0350 (5)	−0.0006 (4)	0.0137 (4)	−0.0018 (4)
C1	0.0416 (6)	0.0331 (6)	0.0301 (6)	−0.0022 (5)	0.0179 (5)	0.0026 (4)
C2	0.0275 (5)	0.0315 (5)	0.0267 (5)	0.0006 (4)	0.0082 (4)	0.0021 (4)
C3	0.0394 (6)	0.0341 (6)	0.0390 (6)	−0.0078 (5)	0.0211 (5)	−0.0008 (5)

N1—C2	1.4924 (16)	C2—C3	1.5201 (16)
C1—C2	1.5130 (17)	C2—H21	0.928 (15)
C1—C3i	1.5259 (18)	C3—C1i	1.5259 (18)
C1—H11	0.959 (17)	C3—H31	0.927 (17)
C1—H12	0.941 (19)	C3—H32	1.008 (17)
C2—N1—H1	110.2 (11)	N1—C2—C3	109.47 (10)
C2—N1—H2	114.4 (13)	N1—C2—C1	109.79 (10)
H1—N1—H2	105.8 (16)	C3—C2—C1	111.39 (10)
C2—N1—H3	111.6 (12)	N1—C2—H21	107.7 (9)
H1—N1—H3	107.8 (16)	C3—C2—H21	107.6 (9)
H2—N1—H3	106.8 (18)	C1—C2—H21	110.8 (9)
C2—C1—C3i	110.91 (10)	C2—C3—C1i	110.36 (10)
C2—C1—H11	108.6 (10)	C2—C3—H31	108.1 (11)
C3i—C1—H11	110.0 (10)	C1i—C3—H31	109.5 (10)
C2—C1—H12	110.8 (10)	C2—C3—H32	107.4 (10)
C3i—C1—H12	110.9 (10)	C1i—C3—H32	110.8 (10)
H11—C1—H12	105.6 (15)	H31—C3—H32	110.6 (15)
C3i—C1—C2—N1	178.07 (10)	N1—C2—C3—C1i	−177.94 (11)
C3i—C1—C2—C3	56.65 (16)	C1—C2—C3—C1i	−56.34 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3···Cl1ii	0.88 (2)	2.30 (2)	3.1734 (15)	170.3 (16)
N1—H2···Cl1iii	0.86 (2)	2.33 (2)	3.1833 (13)	171.9 (17)
N1—H1···Cl1	0.93 (2)	2.23 (2)	3.1584 (13)	173.9 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H3⋯Cl1ii	0.88 (2)	2.30 (2)	3.1734 (15)	170.3 (16)
N1—H2⋯Cl1iii	0.86 (2)	2.33 (2)	3.1833 (13)	171.9 (17)
N1—H1⋯Cl1	0.93 (2)	2.23 (2)	3.1584 (13)	173.9 (16)

Symmetry codes: (ii) ; (iii) .