1,4,10,13-Tetra-oxa-7,16-diazo-niacyclo-octadecane bis-[tetra-chloridoaurate(III)] dihydrate.

The asymmetric unit of the title compound, (C(12)H(28)N(2)O(4))[AuCl(4)](2)·2H(2)O, contains one half-cation, one anion and one water mol-ecule; the cation is centrosymmetric. The Au ion has a square-planar coordination. In the crystal structure, intra-molecular N-H⋯O and O-H⋯O, and inter-molecular N-H⋯O, O-H⋯Cl and N-H⋯Cl hydrogen bonds link the ions and water mol-ecules, forming a supra-molecular structure.

Related literature

For related literature, see: Calleja et al. (2001 ▶); Chekhlov (2000 ▶, 2001 ▶, 2005 ▶); Chekhlov & Martynov (1998 ▶); Chekhlov et al. (1994 ▶); Fonari et al. (2004 ▶); Hasan et al. (1999 ▶); Johnson & Steed (1998 ▶); Moers et al. (2000 ▶); Simonov et al. (2003 ▶); Yap et al. (1995 ▶); Yousefi, Amani & Khavasi (2007 ▶); Yousefi, Teimouri et al. (2007 ▶); Zhang et al. (2006 ▶).

Experimental

Crystal data

(C12H28n class="Chemical">N2O4)[AuCl4]2·2H2O

M = 977.94

Triclinic,

a = 8.0168 (10) Å

b = 8.3359 (9) Å

c = 11.2989 (15) Å

α = 73.063 (11)°

β = 75.965 (10)°

γ = 74.929 (9)°

V = 686.02 (15) Å3

Z = 1

Mo Kα radiation

μ = 11.49 mm−1

T = 120 (2) K

0.32 × 0.22 × 0.20 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: numerical (X-SHAPE and X-RED; Stoe & Cie, 2005 ▶)T min = 0.065, T max = 0.108

4188 measured reflections

2390 independent reflections

2381 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.017

wR(F 2) = 0.045

S = 1.18

2390 reflections

144 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 e Å−3

Δρmin = −0.67 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808015353/hk2465sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015353/hk2465Isup2.hkl

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

(C12H28N2O4)[AuCl4]2·2H2O	Z = 1
Mr = 977.94	F000 = 460
Triclinic, P1	Dx = 2.367 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.0168 (10) Å	Cell parameters from 1139 reflections
b = 8.3359 (9) Å	θ = 1.9–25.2º
c = 11.2989 (15) Å	µ = 11.49 mm−1
α = 73.063 (11)º	T = 120 (2) K
β = 75.965 (10)º	Block, yellow
γ = 74.929 (9)º	0.32 × 0.22 × 0.20 mm
V = 686.02 (15) Å3

Stoe IPDSII diffractometer	2390 independent reflections
Radiation source: fine-focus sealed tube	2381 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.027
Detector resolution: 0.15 mm pixels mm-1	θmax = 25.2º
T = 120(2) K	θmin = 1.9º
rotation method scans	h = −9→8
Absorption correction: numericalshape of crystal determined optically	k = −9→8
Tmin = 0.065, Tmax = 0.108	l = −12→12
4188 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)] = 0.017	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.045	w = 1/[σ2(Fo2) + (0.0216P)2 + 1.1824P] where P = (Fo2 + 2Fc2)/3
S = 1.18	(Δ/σ)max = 0.018
2390 reflections	Δρmax = 0.59 e Å−3
144 parameters	Δρmin = −0.67 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. (X-SHAPE and X-RED; Stoe & Cie, 2005)

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 > 2sigma(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
Au1	0.774200 (17)	0.949008 (17)	0.436516 (13)	0.01917 (8)
Cl1	0.65158 (14)	0.91699 (13)	0.64419 (10)	0.0271 (2)
Cl2	0.77516 (14)	0.66859 (13)	0.45325 (10)	0.0249 (2)
Cl3	0.88196 (14)	0.98407 (13)	0.22535 (10)	0.0257 (2)
Cl4	0.79013 (16)	1.22269 (14)	0.42240 (12)	0.0362 (3)
O1	0.8055 (4)	0.5576 (4)	−0.1123 (3)	0.0230 (6)
O2	0.6857 (4)	0.6728 (3)	0.1006 (3)	0.0227 (6)
O3	0.6136 (4)	0.3371 (5)	0.0862 (4)	0.0259 (7)
H3C	0.666 (7)	0.406 (7)	0.049 (5)	0.019 (15)*
H3D	0.689 (8)	0.264 (8)	0.118 (5)	0.034 (17)*
N1	0.3824 (4)	0.5189 (4)	0.2598 (3)	0.0193 (7)
H1C	0.4424	0.4823	0.1909	0.023*
H1D	0.3672	0.4259	0.3230	0.023*
C1	0.7938 (5)	0.3778 (5)	−0.2343 (4)	0.0231 (9)
H1A	0.7787	0.2856	−0.1594	0.028*
H1B	0.8544	0.3272	−0.3043	0.028*
C2	0.9019 (5)	0.4874 (5)	−0.2162 (4)	0.0228 (9)
H2A	1.0152	0.4194	−0.1983	0.027*
H2B	0.9210	0.5783	−0.2913	0.027*
C3	0.8743 (5)	0.6921 (5)	−0.0984 (4)	0.0232 (9)
H3A	0.9062	0.7677	−0.1798	0.028*
H3B	0.9779	0.6447	−0.0597	0.028*
C4	0.7321 (6)	0.7883 (5)	−0.0161 (4)	0.0259 (9)
H4A	0.7733	0.8800	−0.0025	0.031*
H4B	0.6303	0.8385	−0.0566	0.031*
C5	0.5532 (5)	0.7528 (5)	0.1851 (4)	0.0242 (9)
H5A	0.4568	0.8215	0.1431	0.029*
H5B	0.5998	0.8274	0.2147	0.029*
C6	0.4895 (5)	0.6163 (5)	0.2940 (4)	0.0232 (9)
H6A	0.4190	0.6689	0.3610	0.028*
H6B	0.5900	0.5367	0.3257	0.028*

	U11	U22	U33	U12	U13	U23
Au1	0.01758 (11)	0.01715 (11)	0.02133 (12)	−0.00433 (7)	−0.00015 (7)	−0.00455 (7)
Cl1	0.0296 (5)	0.0268 (5)	0.0227 (6)	−0.0041 (4)	−0.0003 (4)	−0.0077 (4)
Cl2	0.0334 (6)	0.0204 (5)	0.0217 (5)	−0.0106 (4)	−0.0006 (4)	−0.0055 (4)
Cl3	0.0271 (5)	0.0229 (5)	0.0236 (5)	−0.0074 (4)	0.0019 (4)	−0.0037 (4)
Cl4	0.0433 (7)	0.0205 (5)	0.0411 (7)	−0.0105 (5)	0.0085 (5)	−0.0118 (5)
O1	0.0223 (14)	0.0256 (15)	0.0229 (16)	−0.0110 (12)	0.0022 (12)	−0.0083 (12)
O2	0.0249 (15)	0.0196 (14)	0.0227 (16)	−0.0063 (12)	−0.0022 (12)	−0.0039 (12)
O3	0.0223 (17)	0.0229 (17)	0.0312 (19)	−0.0092 (16)	0.0008 (15)	−0.0049 (14)
N1	0.0197 (17)	0.0206 (17)	0.0162 (17)	−0.0061 (13)	0.0016 (14)	−0.0046 (14)
C1	0.020 (2)	0.023 (2)	0.027 (2)	−0.0009 (16)	−0.0022 (17)	−0.0108 (18)
C2	0.018 (2)	0.027 (2)	0.022 (2)	−0.0043 (17)	0.0019 (17)	−0.0077 (18)
C3	0.023 (2)	0.024 (2)	0.025 (2)	−0.0102 (17)	−0.0032 (17)	−0.0057 (18)
C4	0.032 (2)	0.019 (2)	0.027 (2)	−0.0099 (18)	−0.0062 (19)	−0.0021 (17)
C5	0.025 (2)	0.021 (2)	0.029 (2)	−0.0057 (17)	−0.0029 (18)	−0.0100 (18)
C6	0.022 (2)	0.026 (2)	0.026 (2)	−0.0046 (17)	−0.0044 (17)	−0.0123 (18)

Cl1—Au1	2.2796 (11)	C2—H2B	0.9700
Cl2—Au1	2.2877 (10)	C3—O1	1.432 (5)
Cl3—Au1	2.2912 (11)	C3—C4	1.500 (6)
Cl4—Au1	2.2751 (11)	C3—H3A	0.9700
O3—H3C	0.71 (6)	C3—H3B	0.9700
O3—H3D	0.76 (6)	C4—O2	1.419 (5)
N1—C1i	1.496 (5)	C4—H4A	0.9700
N1—H1C	0.9000	C4—H4B	0.9700
N1—H1D	0.9000	C5—O2	1.412 (5)
C1—C2	1.495 (6)	C5—C6	1.501 (6)
C1—N1i	1.496 (5)	C5—H5A	0.9700
C1—H1A	0.9700	C5—H5B	0.9700
C1—H1B	0.9700	C6—N1	1.501 (5)
C2—O1	1.429 (5)	C6—H6A	0.9700
C2—H2A	0.9700	C6—H6B	0.9700
Cl4—Au1—Cl1	90.20 (4)	H2A—C2—H2B	108.6
Cl4—Au1—Cl2	176.52 (4)	O1—C3—C4	106.8 (3)
Cl1—Au1—Cl2	89.96 (4)	O1—C3—H3A	110.4
Cl4—Au1—Cl3	90.30 (4)	C4—C3—H3A	110.4
Cl1—Au1—Cl3	176.79 (3)	O1—C3—H3B	110.4
Cl2—Au1—Cl3	89.74 (4)	C4—C3—H3B	110.4
C2—O1—C3	113.3 (3)	H3A—C3—H3B	108.6
C5—O2—C4	112.8 (3)	O2—C4—C3	108.8 (3)
H3C—O3—H3D	103 (6)	O2—C4—H4A	109.9
C1i—N1—C6	113.5 (3)	C3—C4—H4A	109.9
C1i—N1—H1C	108.9	O2—C4—H4B	109.9
C6—N1—H1C	108.9	C3—C4—H4B	109.9
C1i—N1—H1D	108.9	H4A—C4—H4B	108.3
C6—N1—H1D	108.9	O2—C5—C6	108.5 (3)
H1C—N1—H1D	107.7	O2—C5—H5A	110.0
C2—C1—N1i	110.8 (3)	C6—C5—H5A	110.0
C2—C1—H1A	109.5	O2—C5—H5B	110.0
N1i—C1—H1A	109.5	C6—C5—H5B	110.0
C2—C1—H1B	109.5	H5A—C5—H5B	108.4
N1i—C1—H1B	109.5	C5—C6—N1	112.9 (3)
H1A—C1—H1B	108.1	C5—C6—H6A	109.0
O1—C2—C1	106.6 (3)	N1—C6—H6A	109.0
O1—C2—H2A	110.4	C5—C6—H6B	109.0
C1—C2—H2A	110.4	N1—C6—H6B	109.0
O1—C2—H2B	110.4	H6A—C6—H6B	107.8
C1—C2—H2B	110.4
N1i—C1—C2—O1	59.1 (4)	C1—C2—O1—C3	−168.3 (3)
O1—C3—C4—O2	58.5 (4)	C4—C3—O1—C2	162.2 (3)
O2—C5—C6—N1	−71.6 (4)	C6—C5—O2—C4	169.1 (3)
C5—C6—N1—C1i	−70.3 (4)	C3—C4—O2—C5	179.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1i	0.90	2.49	2.791 (5)	100
N1—H1C···O3	0.90	1.98	2.844 (3)	160
N1—H1D···Cl1ii	0.90	2.81	3.540 (4)	139
N1—H1D···Cl2ii	0.90	2.49	3.262 (3)	143
O3—H3C···O1	0.76 (6)	2.14 (6)	2.858 (4)	158 (6)
O3—H3C···O2	0.76 (6)	2.51 (6)	3.057 (3)	130 (5)
O3—H3D···Cl3iii	0.81 (7)	2.59 (6)	3.378 (4)	167.00

Cl1—Au1	2.2796 (11)
Cl2—Au1	2.2877 (10)
Cl3—Au1	2.2912 (11)
Cl4—Au1	2.2751 (11)

Cl4—Au1—Cl1	90.20 (4)
Cl4—Au1—Cl2	176.52 (4)
Cl1—Au1—Cl2	89.96 (4)
Cl4—Au1—Cl3	90.30 (4)
Cl1—Au1—Cl3	176.79 (3)
Cl2—Au1—Cl3	89.74 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O1i	0.90	2.49	2.791 (5)	100
N1—H1C⋯O3	0.90	1.98	2.844 (3)	160
N1—H1D⋯Cl1ii	0.90	2.81	3.540 (4)	139
N1—H1D⋯Cl2ii	0.90	2.49	3.262 (3)	143
O3—H3C⋯O1	0.76 (6)	2.14 (6)	2.858 (4)	158 (6)
O3—H3C⋯O2	0.76 (6)	2.51 (6)	3.057 (3)	130 (5)
O3—H3D⋯Cl3iii	0.81 (7)	2.59 (6)	3.378 (4)	167.00

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