N,N',N''-Tricyclo-hexyl-guanidinium iodide.

In the title compound, C(19)H(36)N(3) (+)·I(-), the orientation of the cyclo-hexyl rings around the planar (sum of N-C-N angles = 360°) CN(3) (+) unit produces steric hindrance around the N-H groups. As a consequence of this particular orientation of the tricyclo-hexyl-guanidinium cation (hereafter denoted CHGH(+)), hydrogen bonding is restricted to classical N-H⋯I and non-clasical (cyclo-hex-yl)C-H⋯I hydrogen bonds. The propeller CHGH(+) cation and the oriented hydrogen-bonding interactions lead to a three-dimensional supra-molecular structure.

Related literature

For background to guanidines, see: Ishikawa & Isobe (2002 ▶); Moroni et al. (2001 ▶); Yoshiizumi et al. (1998 ▶). The title salt is isomorphous with the chloride anion-analogue (Cai & Hu, 2006 ▶) and N,N′,N′′-triisopropyl­guanidinium chloride (Said et al., 2005 ▶). (Ishikawa & Isobe, 2002 ▶). The structural features and hydrogen -bonding array provided by guanidinium cations suggest them to be good building blocks for the formation of supra­molecular entities, see: Said, Bazinet et al. (2006 ▶); Said, Ong et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H36N3 +·I−

M = 433.41

Cubic,

a = 12.893 (4) Å

V = 2143 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.50 mm−1

T = 188 K

0.5 × 0.3 × 0.3 mm

Data collection

Bruker P4 diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.271, T max = 0.320

2387 measured reflections

802 independent reflections

628 reflections with I > 2σ(I)

R int = 0.055

3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.076

S = 1.04

802 reflections

70 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 802 Friedel pairs

Flack parameter: 0.08 (8)

Data collection: XSCANS (Bruker, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; 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 datablock(s) I, global. DOI: 10.1107/S1600536811049683/bq2321sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811049683/bq2321Isup2.mol

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049683/bq2321Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811049683/bq2321Isup4.cml

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

C19H36N3+·I−	Dx = 1.343 Mg m−3
Mr = 433.41	Mo Kα radiation, λ = 0.71073 Å
Cubic, P213	Cell parameters from 30 reflections
Hall symbol: P 2ac 2ab 3	θ = 3.9–6.9°
a = 12.893 (4) Å	µ = 1.50 mm−1
V = 2143 (2) Å3	T = 188 K
Z = 4	Block, colorless
F(000) = 896	0.5 × 0.3 × 0.3 mm

Bruker P4 diffractometer	628 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
graphite	θmax = 25.9°, θmin = 2.2°
ω scans	h = 0→15
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = 0→15
Tmin = 0.271, Tmax = 0.320	l = 0→15
2387 measured reflections	3 standard reflections every 97 reflections
802 independent reflections	intensity decay: none

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.0269P)2 + 0.7683P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
802 reflections	Δρmax = 0.33 e Å−3
70 parameters	Δρmin = −0.27 e Å−3
0 restraints	Absolute structure: Flack (1983), 802 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.08 (8)

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
I1	0.89107 (4)	0.89107 (4)	0.89107 (4)	0.0589 (2)
N1	0.8894 (5)	0.1398 (4)	0.7489 (4)	0.0715 (16)
H1A	0.8803	0.0781	0.7728	0.086*
C1	0.8343 (6)	0.1657 (6)	0.6657 (6)	0.064 (3)
C2	0.9631 (6)	0.2045 (6)	0.8033 (6)	0.071 (2)
H2A	0.9812	0.2636	0.7591	0.086*
C3	0.9164 (6)	0.2440 (8)	0.9017 (8)	0.114 (4)
H3A	0.8951	0.1861	0.9448	0.137*
H3B	0.8556	0.2855	0.8862	0.137*
C4	0.9957 (9)	0.3091 (9)	0.9588 (11)	0.149 (5)
H4A	1.0115	0.3701	0.9177	0.179*
H4B	0.9660	0.3323	1.0239	0.179*
C5	1.0919 (7)	0.2525 (9)	0.9799 (7)	0.100 (3)
H5A	1.0780	0.1967	1.0285	0.120*
H5B	1.1419	0.2990	1.0116	0.120*
C6	1.1359 (5)	0.2091 (7)	0.8838 (7)	0.084 (2)
H6A	1.1957	0.1668	0.9009	0.101*
H6C	1.1593	0.2654	0.8397	0.101*
C7	1.0581 (6)	0.1441 (7)	0.8255 (7)	0.086 (3)
H7C	1.0885	0.1206	0.7608	0.103*
H7A	1.0404	0.0835	0.8663	0.103*

	U11	U22	U33	U12	U13	U23
I1	0.0589 (2)	0.0589 (2)	0.0589 (2)	−0.0007 (3)	−0.0007 (3)	−0.0007 (3)
N1	0.084 (4)	0.060 (3)	0.070 (4)	−0.014 (4)	−0.026 (4)	0.014 (3)
C1	0.064 (3)	0.064 (3)	0.064 (3)	−0.012 (4)	−0.012 (4)	0.012 (4)
C2	0.082 (6)	0.071 (5)	0.061 (5)	−0.020 (5)	−0.024 (4)	0.010 (4)
C3	0.082 (7)	0.132 (8)	0.129 (9)	0.040 (6)	−0.022 (7)	−0.045 (8)
C4	0.129 (9)	0.147 (10)	0.172 (12)	0.014 (9)	−0.035 (9)	−0.102 (10)
C5	0.097 (7)	0.138 (8)	0.065 (5)	−0.021 (8)	−0.028 (6)	0.008 (6)
C6	0.064 (5)	0.090 (6)	0.098 (6)	−0.014 (4)	−0.005 (5)	0.007 (6)
C7	0.049 (4)	0.104 (7)	0.105 (6)	−0.010 (4)	−0.001 (5)	−0.026 (6)

N1—C1	1.330 (5)	C4—C5	1.465 (13)
N1—C2	1.446 (9)	C4—H4A	0.9700
N1—H1A	0.8600	C4—H4B	0.9700
C1—N1i	1.330 (5)	C5—C6	1.473 (13)
C1—N1ii	1.330 (5)	C5—H5A	0.9700
C2—C7	1.479 (10)	C5—H5B	0.9700
C2—C3	1.493 (11)	C6—C7	1.508 (10)
C2—H2A	0.9800	C6—H6A	0.9700
C3—C4	1.514 (13)	C6—H6C	0.9700
C3—H3A	0.9700	C7—H7C	0.9700
C3—H3B	0.9700	C7—H7A	0.9700
C1—N1—C2	126.7 (5)	C5—C4—H4B	109.1
C1—N1—H1A	116.7	C3—C4—H4B	109.1
C2—N1—H1A	116.7	H4A—C4—H4B	107.8
N1i—C1—N1	119.99 (3)	C4—C5—C6	111.1 (8)
N1i—C1—N1ii	119.99 (3)	C4—C5—H5A	109.4
N1—C1—N1ii	119.99 (3)	C6—C5—H5A	109.4
N1—C2—C7	109.5 (6)	C4—C5—H5B	109.4
N1—C2—C3	110.1 (7)	C6—C5—H5B	109.4
C7—C2—C3	110.4 (7)	H5A—C5—H5B	108.0
N1—C2—H2A	108.9	C5—C6—C7	112.0 (7)
C7—C2—H2A	108.9	C5—C6—H6A	109.2
C3—C2—H2A	108.9	C7—C6—H6A	109.2
C2—C3—C4	109.3 (8)	C5—C6—H6C	109.2
C2—C3—H3A	109.8	C7—C6—H6C	109.2
C4—C3—H3A	109.8	H6A—C6—H6C	107.9
C2—C3—H3B	109.8	C2—C7—C6	110.8 (7)
C4—C3—H3B	109.8	C2—C7—H7C	109.5
H3A—C3—H3B	108.3	C6—C7—H7C	109.5
C5—C4—C3	112.7 (8)	C2—C7—H7A	109.5
C5—C4—H4A	109.1	C6—C7—H7A	109.5
C3—C4—H4A	109.1	H7C—C7—H7A	108.1

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···I1iii	0.86	2.86	3.693 (5)	165
C2—H2A···I1iv	0.98	3.03	3.950 (5)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯I1i	0.86	2.86	3.693 (5)	165
C2—H2A⋯I1ii	0.98	3.03	3.950 (5)	158

Symmetry codes: (i) ; (ii) .