5,7,7,12,14,14-Hexamethyl-4,8-diaza-1,11-diazo­niocyclotetra­deca-4,11-diene diiodide dihydrate

Kennedy, A.R.; Lutta, S.T.; Morrison, C.A.; Okoth, M.O.; Orang'o, D.M.

doi:10.1107/S1600536811005848

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages o682-o683

doi:10.1107/S1600536811005848

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5,7,7,12,14,14-Hexamethyl-4,8-diaza-1,11-diazoniocyclotetradeca-4,11-diene diiodide dihydrate

Alan R. Kennedy,^a Samwel T. Lutta,^b Catriona A. Morrison,^a Maurice O. Okoth ^b ^* and Daniel M. Orang'o ^b

^aDepartment of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland, and ^bDepartment of Chemistry and Biochemistry, Moi University, PO Box 1125-30100, Eldoret, Kenya
^*Correspondence e-mail: okothmdo@mu.ac.ke

(Received 26 January 2011; accepted 16 February 2011; online 23 February 2011)

The asymmetric unit of the title compound, C₁₆H₃₄N₄²⁺·2I⁻·2H₂O, contains one half-cation, one iodide anion and one water molecule. The cation has crystallographically imposed centrosymmetric symmetry. Despite some differences in the unit-cell dimensions, packing analysis on a cluster of 15 cations and a comparison of the hydrogen bonding suggests that this compound is isostructural with its bromide analogue. Intermolecular hydrogen bonding forms eight-membered [H—O—H⋯I]₂ and [H—N—H⋯I]₂ rings and creates a sheet structure.

Related literature

For the preparation and structure of the equivalent bromide salt, see: Rohovec et al. (1999 ). For the structure of the perchlorate salt, see: Bi et al. (2008 ). For structures of representative transition metal complexes, see: Bieńko et al. (2007 ); Yang (2005 ); Ballester et al. (2000 ); Endicott et al. (1981 ); Wester et al. (1977 ); Goedken et al. (1973 ). Macrocyclic metal complexes have been studied extensively owing to their similarity to metallobiomolecules, and in order to further understanding of biological mechanisms, see: Merrell et al. (1977 ). The packing analysis was performed with Mercury (Macrae et al., 2008 ).

Experimental

Crystal data

C₁₆H₃₄N₄²⁺·2I⁻·2H₂O
M_r = 572.30
Triclinic, $[P \overline 1]$
a = 8.4098 (3) Å
b = 8.7252 (2) Å
c = 8.7724 (3) Å
α = 74.673 (2)°
β = 66.267 (1)°
γ = 75.809 (2)°
V = 561.24 (3) Å³
Z = 1
Mo Kα radiation
μ = 2.82 mm⁻¹
T = 120 K
0.20 × 0.14 × 0.10 mm

Data collection

Bruker–Nonius Roper CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.673, T_max = 0.746
12010 measured reflections
2563 independent reflections
2478 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.046
S = 1.18
2563 reflections
127 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.99 e Å⁻³
Δρ_min = −0.75 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2ⁱ	0.89 (3)	2.04 (3)	2.744 (2)	136 (2)
O1W—H1W⋯I1	0.88 (2)	2.71 (2)	3.5753 (18)	171 (3)
O1W—H2W⋯I1ⁱⁱ	0.87 (2)	2.68 (2)	3.5494 (17)	176 (3)
N1—H2N⋯I1ⁱⁱ	0.81 (3)	3.23 (3)	3.6895 (17)	119 (2)
N1—H2N⋯I1ⁱⁱⁱ	0.81 (3)	2.99 (3)	3.7110 (18)	149 (2)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+1, -z+1; (iii) x+1, y, z-1.

Data collection: COLLECT (Hooft, 1988 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT ; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005848/rk2263sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005848/rk2263Isup2.hkl

checkCIF report

Comment top

Macrocyclic metal complexes have been studied extensively owing to their similarity to metallobiomolecules, and in order to further understanding of biological mechanisms (Merril et al., 1977). The title molecule, 5,7,7,12,14, 14–hexamethyl–4,8–diaza–1,11–diazoniocyclo–4,11–tetradecadiene diiodide dihydrate, I, is the hydroiodide salt of an imine based ligand that has been used extensively to form complexes with the later first row transition metals. These are typically cobalt, nickel and copper complexes (see, for example, Endicott et al., 1981; Ballester et al., 2000; Bieńko et al., 2007) but structural examples with iron, zinc and even chromium are also known (Goedken et al., 1973; Yang, 2005; Wester et al., 1977). The structures of the free base and of the bromide and perchlorate salts have also been reported (Rohovec et al., 1999; Bi et al., 2008).

The macrocyclic dication has crystallographically imposed centrosymetric symmetry, Z' = 1/2, with protonation at the amine N–atoms rather than at the imine groups (Fig. 1). The unit–cell parameters are somewhat similar to those of the bromide analogue (Rohovec et al., 1999) measured at room temperature. However, there is a difference in that the most acute angle subtends the longest and shortest cell axes in I, but subtends the shortest and middle length cell axes in the iodide salt. To check if this was a structurally significant variation the "crystal packing similarity" module of Mercury CSD 2.3 was used (Macrae et al., 2008). This analysis of the largest molecular component in the array (here the macrocyclic cation) showed that a molecular cluster of fifteen cations from each salt matched to within distance and torsion angle variations of 20%. Thus the two structures are isostructural, see overlay in Fig. 2.

Classical intramolecular N—H···N hydrogen–bonding joins the amine and imine N–atoms across the macrocycle. There are also four independent intermolecular hydrogen–bonds. All involve iodide as the acceptor with both water H–atoms acting as donors and atom H2N acting as a donor in two seperate interactions, see Table 1. Eight membered [H—O—H···I]₂ and [H—N—H···I]₂ rings support a two dimensional sheet structure propagated largely through N—H···I interactions. This is again similar to the bromide structure and so their isostructural nature is confirmed.

Related literature top

For the preparation and structure of the equivalent bromide salt, see: Rohovec et al. (1999). For the structure of the perchlorate salt, see: Bi et al. (2008). For structures of representative transition metal complexes, see: Bieńko et al. (2007); Yang (2005); Ballester et al. (2000); Endicott et al. (1981); Wester et al. (1977); Goedken et al. (1973). Macrocyclic metal complexes have been studied extensively owing to their similarity to metallobiomolecules, and in order to further understanding of biological mechanisms, see: Merrell et al. (1977). The packing analysis was performed with Mercury (Macrae et al., 2008).

Experimental top

A 0.2 mol (13.2 mL) sample of ethylenediamine (ED) was put into 10 ml absolute ethanol and cooled in an ice bath for about 10 minutes. A 0.2 mol (36.2 ml of 55%) sample of hydroiodic acid was slowly added to the cool ED solution. Care was taken not to let the solution to boil over. After the addition of HI, 30 mL of acetone was added (an excess of 0.4 mL was required) and the solution allowed to cool in an ice bath overnight. The colourless crystalline material was filtered from solution. It was washed in absolute EtOH and dried in air for 30 minutes (yield 6.221 g).

Computing details top

Data collection: COLLECT (Hooft, 1988); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1988); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1988); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the macrocyclic dication with atom numbering scheme. Displacement ellipsoids are drawn at 50% probability level H atoms are presented as a small sphertes of arbitrary radius. Symmetry code: (i) 1-x, 1-y, -z.
	Fig. 2. Overlaid packing diagram, showing cations from the iodide structure in green and those from the bromide structure in blue.

5,7,7,12,14,14-Hexamethyl-4,8-diaza-1,11-diazoniocyclotetradeca-4,11-diene diiodide dihydrate top

Crystal data top

C₁₆H₃₄N₄²⁺·2I⁻·2H₂O	Z = 1
M_r = 572.30	F(000) = 284
Triclinic, P1	D_x = 1.693 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4098 (3) Å	Cell parameters from 10421 reflections
b = 8.7252 (2) Å	θ = 2.9–27.5°
c = 8.7724 (3) Å	µ = 2.82 mm⁻¹
α = 74.673 (2)°	T = 120 K
β = 66.267 (1)°	Block, colourless
γ = 75.809 (2)°	0.20 × 0.14 × 0.10 mm
V = 561.24 (3) Å³

Data collection top

Bruker–Nonius Roper CCD diffractometer	2563 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	2478 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −11→11
T_min = 0.673, T_max = 0.746	l = −11→11
12010 measured reflections

Refinement top

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)] = 0.019	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.046	w = 1/[σ²(F_o²) + (0.0124P)² + 0.33P] where P = (F_o² + 2F_c²)/3
S = 1.18	(Δ/σ)_max = 0.001
2563 reflections	Δρ_max = 0.99 e Å⁻³
127 parameters	Δρ_min = −0.75 e Å⁻³
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0243 (13)

Crystal data top

C₁₆H₃₄N₄²⁺·2I⁻·2H₂O	γ = 75.809 (2)°
M_r = 572.30	V = 561.24 (3) Å³
Triclinic, P1	Z = 1
a = 8.4098 (3) Å	Mo Kα radiation
b = 8.7252 (2) Å	µ = 2.82 mm⁻¹
c = 8.7724 (3) Å	T = 120 K
α = 74.673 (2)°	0.20 × 0.14 × 0.10 mm
β = 66.267 (1)°

Data collection top

Bruker–Nonius Roper CCD diffractometer	2563 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2478 reflections with I > 2σ(I)
T_min = 0.673, T_max = 0.746	R_int = 0.030
12010 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	3 restraints
wR(F²) = 0.046	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	Δρ_max = 0.99 e Å⁻³
2563 reflections	Δρ_min = −0.75 e Å⁻³
127 parameters

Special details top

Experimental. Southampton NCS collection 2010src0073

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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

	x	y	z	U_iso*/U_eq
I1	0.214555 (16)	0.460869 (15)	0.757490 (15)	0.02330 (8)
O1W	0.6274 (2)	0.21795 (19)	0.5780 (2)	0.0336 (4)
H1W	0.525 (3)	0.270 (3)	0.633 (3)	0.050*
H2W	0.671 (3)	0.295 (3)	0.496 (3)	0.050*
N1	0.7414 (2)	0.60362 (18)	−0.1726 (2)	0.0139 (3)
N2	0.6077 (2)	0.29338 (18)	0.0038 (2)	0.0165 (3)
C1	0.7419 (3)	0.4771 (2)	−0.2576 (2)	0.0185 (4)
H1A	0.8389	0.4822	−0.3694	0.022*
H1B	0.6296	0.4954	−0.2762	0.022*
C2	0.7653 (3)	0.3134 (2)	−0.1486 (3)	0.0209 (4)
H2A	0.7880	0.2286	−0.2140	0.025*
H2B	0.8680	0.3019	−0.1159	0.025*
C3	0.6167 (3)	0.1933 (2)	0.1357 (3)	0.0174 (4)
C4	0.4514 (3)	0.1743 (2)	0.2906 (2)	0.0182 (4)
H4A	0.4494	0.2381	0.3696	0.022*
H4B	0.4604	0.0599	0.3474	0.022*
C5	0.2753 (3)	0.2226 (2)	0.2659 (2)	0.0158 (4)
C6	0.7788 (3)	0.0876 (3)	0.1592 (3)	0.0275 (5)
H6A	0.7804	−0.0226	0.1507	0.041*
H6B	0.7780	0.0881	0.2711	0.041*
H6C	0.8836	0.1283	0.0712	0.041*
C7	0.2617 (3)	0.1223 (2)	0.1546 (3)	0.0214 (4)
H7A	0.1452	0.1527	0.1456	0.032*
H7B	0.2788	0.0079	0.2052	0.032*
H7C	0.3523	0.1417	0.0414	0.032*
C8	0.1260 (3)	0.2045 (2)	0.4379 (3)	0.0235 (4)
H8A	0.1421	0.2616	0.5118	0.035*
H8B	0.1266	0.0902	0.4895	0.035*
H8C	0.0134	0.2502	0.4230	0.035*
H1N	0.649 (3)	0.599 (3)	−0.076 (3)	0.020 (6)*
H2N	0.829 (4)	0.584 (3)	−0.149 (3)	0.029 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01952 (10)	0.03155 (11)	0.01896 (10)	−0.00480 (6)	−0.00879 (7)	−0.00124 (6)
O1W	0.0384 (10)	0.0238 (8)	0.0371 (10)	−0.0029 (7)	−0.0157 (8)	−0.0017 (7)
N1	0.0139 (8)	0.0133 (7)	0.0155 (8)	−0.0038 (6)	−0.0075 (7)	0.0007 (6)
N2	0.0160 (8)	0.0143 (7)	0.0190 (8)	−0.0048 (6)	−0.0052 (7)	−0.0025 (6)
C1	0.0213 (10)	0.0168 (9)	0.0173 (10)	−0.0052 (7)	−0.0053 (8)	−0.0036 (7)
C2	0.0180 (10)	0.0141 (9)	0.0256 (11)	−0.0041 (7)	−0.0017 (8)	−0.0040 (8)
C3	0.0173 (9)	0.0153 (9)	0.0240 (10)	−0.0027 (7)	−0.0105 (8)	−0.0055 (7)
C4	0.0197 (10)	0.0172 (9)	0.0185 (9)	−0.0036 (7)	−0.0101 (8)	0.0011 (7)
C5	0.0190 (10)	0.0118 (8)	0.0171 (9)	−0.0053 (7)	−0.0092 (8)	0.0031 (7)
C6	0.0221 (11)	0.0293 (11)	0.0303 (12)	0.0028 (8)	−0.0137 (9)	−0.0038 (9)
C7	0.0261 (11)	0.0155 (9)	0.0284 (11)	−0.0071 (8)	−0.0154 (9)	−0.0012 (8)
C8	0.0212 (11)	0.0219 (10)	0.0218 (11)	−0.0070 (8)	−0.0055 (8)	0.0044 (8)

Geometric parameters (Å, º) top

O1W—H1W	0.877 (17)	C4—C5	1.524 (3)
O1W—H2W	0.873 (17)	C4—H4A	0.9900
N1—C1	1.485 (2)	C4—H4B	0.9900
N1—C5ⁱ	1.524 (2)	C5—N1ⁱ	1.524 (2)
N1—H1N	0.89 (3)	C5—C8	1.524 (3)
N1—H2N	0.81 (3)	C5—C7	1.524 (3)
N2—C3	1.269 (3)	C6—H6A	0.9800
N2—C2	1.462 (2)	C6—H6B	0.9800
C1—C2	1.512 (3)	C6—H6C	0.9800
C1—H1A	0.9900	C7—H7A	0.9800
C1—H1B	0.9900	C7—H7B	0.9800
C2—H2A	0.9900	C7—H7C	0.9800
C2—H2B	0.9900	C8—H8A	0.9800
C3—C6	1.504 (3)	C8—H8B	0.9800
C3—C4	1.510 (3)	C8—H8C	0.9800

H1W—O1W—H2W	101 (2)	C5—C4—H4B	107.8
C1—N1—C5ⁱ	117.45 (15)	H4A—C4—H4B	107.1
C1—N1—H1N	107.0 (15)	N1ⁱ—C5—C4	109.64 (15)
C5ⁱ—N1—H1N	105.9 (15)	N1ⁱ—C5—C8	109.95 (16)
C1—N1—H2N	109.8 (18)	C4—C5—C8	109.65 (16)
C5ⁱ—N1—H2N	108.5 (18)	N1ⁱ—C5—C7	105.81 (15)
H1N—N1—H2N	108 (2)	C4—C5—C7	111.51 (16)
C3—N2—C2	120.48 (17)	C8—C5—C7	110.21 (16)
N1—C1—C2	109.64 (16)	C3—C6—H6A	109.5
N1—C1—H1A	109.7	C3—C6—H6B	109.5
C2—C1—H1A	109.7	H6A—C6—H6B	109.5
N1—C1—H1B	109.7	C3—C6—H6C	109.5
C2—C1—H1B	109.7	H6A—C6—H6C	109.5
H1A—C1—H1B	108.2	H6B—C6—H6C	109.5
N2—C2—C1	110.39 (16)	C5—C7—H7A	109.5
N2—C2—H2A	109.6	C5—C7—H7B	109.5
C1—C2—H2A	109.6	H7A—C7—H7B	109.5
N2—C2—H2B	109.6	C5—C7—H7C	109.5
C1—C2—H2B	109.6	H7A—C7—H7C	109.5
H2A—C2—H2B	108.1	H7B—C7—H7C	109.5
N2—C3—C6	127.05 (19)	C5—C8—H8A	109.5
N2—C3—C4	119.23 (17)	C5—C8—H8B	109.5
C6—C3—C4	113.71 (17)	H8A—C8—H8B	109.5
C3—C4—C5	118.10 (16)	C5—C8—H8C	109.5
C3—C4—H4A	107.8	H8A—C8—H8C	109.5
C5—C4—H4A	107.8	H8B—C8—H8C	109.5
C3—C4—H4B	107.8

C5ⁱ—N1—C1—C2	178.16 (16)	N2—C3—C4—C5	23.3 (3)
C3—N2—C2—C1	−156.80 (17)	C6—C3—C4—C5	−157.41 (17)
N1—C1—C2—N2	69.8 (2)	C3—C4—C5—N1ⁱ	−55.5 (2)
C2—N2—C3—C6	1.3 (3)	C3—C4—C5—C8	−176.29 (16)
C2—N2—C3—C4	−179.47 (16)	C3—C4—C5—C7	61.4 (2)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2ⁱ	0.89 (3)	2.04 (3)	2.744 (2)	136 (2)
O1W—H1W···I1	0.88 (2)	2.71 (2)	3.5753 (18)	171 (3)
O1W—H2W···I1ⁱⁱ	0.87 (2)	2.68 (2)	3.5494 (17)	176 (3)
N1—H2N···I1ⁱⁱ	0.81 (3)	3.23 (3)	3.6895 (17)	119 (2)
N1—H2N···I1ⁱⁱⁱ	0.81 (3)	2.99 (3)	3.7110 (18)	149 (2)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₆H₃₄N₄²⁺·2I⁻·2H₂O
M_r	572.30
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	8.4098 (3), 8.7252 (2), 8.7724 (3)
α, β, γ (°)	74.673 (2), 66.267 (1), 75.809 (2)
V (Å³)	561.24 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.82
Crystal size (mm)	0.20 × 0.14 × 0.10

Data collection
Diffractometer	Bruker–Nonius Roper CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.673, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	12010, 2563, 2478
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.046, 1.18
No. of reflections	2563
No. of parameters	127
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.99, −0.75

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1988), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2ⁱ	0.89 (3)	2.04 (3)	2.744 (2)	136 (2)
O1W—H1W···I1	0.877 (17)	2.706 (18)	3.5753 (18)	171 (3)
O1W—H2W···I1ⁱⁱ	0.873 (17)	2.678 (17)	3.5494 (17)	176 (3)
N1—H2N···I1ⁱⁱ	0.81 (3)	3.23 (3)	3.6895 (17)	119 (2)
N1—H2N···I1ⁱⁱⁱ	0.81 (3)	2.99 (3)	3.7110 (18)	149 (2)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z−1.

Acknowledgements

We are grateful to the National Crystallography Service, University of Southampton, for the data collection. MOO thanks the Commonwealth Scholarship Commission and the British Council for funding and Moi University for sabbatical leave.

References

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Volume 67| Part 3| March 2011| Pages o682-o683

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

5,7,7,12,14,14-Hexa­methyl-4,8-di­aza-1,11-diazo­nio­cyclo­tetra­deca-4,11-diene diiodide dihydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5,7,7,12,14,14-Hexamethyl-4,8-diaza-1,11-diazoniocyclotetradeca-4,11-diene diiodide dihydrate