1,4,10,13-Tetra­oxa-7,16-diazo­niacyclo­octadecane bis­[tetra­chloridoaurate(III)] dihydrate

Hojjat Kashani, L.; Yousefi, M.; Amani, V.; Khavasi, H.R.

doi:10.1107/S1600536808015353

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages m840-m841

doi:10.1107/S1600536808015353

Open

access

1,4,10,13-Tetraoxa-7,16-diazoniacyclooctadecane bis[tetrachloridoaurate(III)] dihydrate

Leila Hojjat Kashani,^a Mohammad Yousefi,^a ^* Vahid Amani ^a and Hamid Reza Khavasi ^b

^aIslamic Azad University, Shahr-e-Rey Branch, Tehran, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, Tehran 1983963113, Iran
^*Correspondence e-mail: myousefi50@yahoo.com

(Received 18 May 2008; accepted 21 May 2008; online 24 May 2008)

The asymmetric unit of the title compound, (C₁₂H₂₈N₂O₄)[AuCl₄]₂·2H₂O, contains one half-cation, one anion and one water molecule; the cation is centrosymmetric. The Au ion has a square-planar coordination. In the crystal structure, intramolecular N—H⋯O and O—H⋯O, and intermolecular N—H⋯O, O—H⋯Cl and N—H⋯Cl hydrogen bonds link the ions and water molecules, forming a supramolecular 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

(C₁₂H₂₈N₂O₄)[AuCl₄]₂·2H₂O
M_r = 977.94
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.017
wR(F²) = 0.045
S = 1.18
2390 reflections
144 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

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) -x+1, -y+1, -z; (ii) -x+1, -y+1, -z+1; (iii) x, y-1, z.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Recently, we reported the synthesis and crystal structure of the [(H₂DA18C6)Cl₂], (II), (Yousefi, Amani & Khavasi, 2007) and [(H₂DA18C6)][PtCl₆].2H₂O, (III), (Yousefi, Teimouri et al., 2007) [where H₂DA18C6 is 1,10-Diazonia-18-crown-6]. Several proton transfer systems using 1,10-diaza-18-crown-6, with proton donor molecules, such as [(H₂DA18C6)I₂.2H₂O], (IV), (Chekhlov, 2005), [(H₂DA18C6)(C₂HO₄)₂], (V), and [(H₂DA18C6)₂(C₂O₄)₂.2H₂O], (VI), (Chekhlov, 2000), [(H₂DA18C6)(picrate)₂], (VII), (Chekhlov, 2001), [(H₂DA18C6)(HPTD)₂], (VIII), (Simonov et al., 2003), [(H₂DA18C6)(PD)₂.(H₂O)₄], (IX), and [(H₂DA18C6)(PS)₂.(H₂O)₂], (X), (Fonari et al., 2004), [(H₂DA18C6)(CCl₃COO)₂(CCl₃COOH)₂], (XI), (Chekhlov et al., 1994), [(H₂DA18C6)(CCl₃COO)₂], (XII), (Chekhlov & Martynov, 1998), and {[H₂DA18C6][(ArSO₂)₂N]₂}, (XIII), (Moers et al., 2000) [where C₂O₄ is oxalate, HPTD is (4Z,5E)-pyrimidine-2,4,5,6(1H,3H) -tetraone 4,5-dioxime anion, PD is 2-(2-methylphenyl)-2H-[1,2,3]- triazolo[4,5-d]pyrimidine-5,7(4H,6H)-dione 3-oxide anion, PS is 6-amino-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-ylsulfamate and (ArSO₂)₂N is bis(4-chlorobenzenesulfonyl)imide] have been synthesized and characterized by single-crystal X-ray diffraction methods.

There are also several proton transfer systems using HAuCl₄ with proton acceptor molecules, such as [EMI][AuCl₄] (XIV) and [BMI]₂[AuCl₄].2H₂O, (XV), (Hasan et al., 1999), [H₂bipy][AuCl₄][Cl], (XVI), (Zhang et al., 2006), [H₇O₃][15-crown-5][AuCl₄], (XVII) and [H₅O₂][benzo-15-crown-5] ₂[AuCl₄], (XVIII), (Johnson & Steed, 1998), [H₅O₂]₂[12-crown-4]₂ [AuCl₄]₂, (XIX), [H₃O][18-crown-6][AuCl₄], (XX) and [H₃O] [4-nitrobenzo-18-crown-6][AuCl₄], (XXI), (Calleja et al., 2001) and [DPpy.H][AuCl₄], (XXII), (Yap et al., 1995) [where EMI is 1-ethyl-3-methylimidazolium, BMI is 1-butyl-3-methylimidazolium, H₂bipy is 2,2'-bipyridinium and DPpy.H is 2,6-Diphenylpyridinium] have been synthesized and characterized by single-crystal X-ray diffraction methods. We report herein the synthesis and crystal structure of the title compound, (I).

The asymmetric unit of (I), (Fig. 1) contains one half-cation, one anion and one water molecule; the cation is centrosymmetric. The Au ion has a square-planar coordination (Table 1). The bond lengths and angles, in cation, are in good agreement with the corresponding values in (II), (III) and (IV). Also, the Au-Cl bond lengths and angles (Table 1) are within normal range [XXII].

In the crystal structure, intramolecular N-H···O and O-H···O and intermolecular N-H···O, O-H···Cl and N-H···Cl hydrogen bonds (Table 2) link the molecules to form a supramolecular structure (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

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 top

For the preparation of the title compound, (I), a solution of 1,10-diaza-18 -crown-6 (0.10 g, 0.37 mmol) in EtOH (20 ml) was added to a solution of HAuCl₄.3H₂O, (0.29 g, 0.74 mmol) in water (30 ml) and the resulting yellow solution was stirred for 10 min at 313 K. Then, it was left to evaporate slowly at room temperature. After one week, yellow prismatic crystals of (I) were isolated (yield; 0.26 g; 72.0%).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); 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).

Figures top

	Fig. 1. The asymmetric unit of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level [symmetry code: (a) 1 - x, 1 - y, -z].
	Fig. 2. A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines.

1,4,10,13-Tetraoxa-7,16-diazoniacyclooctadecane bis[tetrachloridoaurate(III)] dihydrate top

Crystal data top

(C₁₂H₂₈N₂O₄)[AuCl₄]₂·2H₂O	Z = 1
M_r = 977.94	F(000) = 460
Triclinic, P1	D_x = 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 = 1.9–25.2°
c = 11.2989 (15) Å	µ = 11.49 mm⁻¹
α = 73.063 (11)°	T = 120 K
β = 75.965 (10)°	Block, yellow
γ = 74.929 (9)°	0.32 × 0.22 × 0.20 mm
V = 686.02 (15) Å³

Data collection top

Stoe IPDSII diffractometer	2390 independent reflections
Radiation source: fine-focus sealed tube	2381 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 0.15 mm pixels mm^-1	θ_max = 25.2°, θ_min = 1.9°
rotation method scans	h = −9→8
Absorption correction: numerical shape of crystal determined optically	k = −9→8
T_min = 0.065, T_max = 0.108	l = −12→12
4188 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.017	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.045	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ²(F_o²) + (0.0216P)² + 1.1824P] where P = (F_o² + 2F_c²)/3
2390 reflections	(Δ/σ)_max = 0.018
144 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.67 e Å⁻³

Crystal data top

(C₁₂H₂₈N₂O₄)[AuCl₄]₂·2H₂O	γ = 74.929 (9)°
M_r = 977.94	V = 686.02 (15) Å³
Triclinic, P1	Z = 1
a = 8.0168 (10) Å	Mo Kα radiation
b = 8.3359 (9) Å	µ = 11.49 mm⁻¹
c = 11.2989 (15) Å	T = 120 K
α = 73.063 (11)°	0.32 × 0.22 × 0.20 mm
β = 75.965 (10)°

Data collection top

Stoe IPDSII diffractometer	2390 independent reflections
Absorption correction: numerical shape of crystal determined optically	2381 reflections with I > 2σ(I)
T_min = 0.065, T_max = 0.108	R_int = 0.027
4188 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.017	0 restraints
wR(F²) = 0.045	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	Δρ_max = 0.59 e Å⁻³
2390 reflections	Δρ_min = −0.67 e Å⁻³
144 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

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—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) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	(C₁₂H₂₈N₂O₄)[AuCl₄]₂·2H₂O
M_r	977.94
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	8.0168 (10), 8.3359 (9), 11.2989 (15)
α, β, γ (°)	73.063 (11), 75.965 (10), 74.929 (9)
V (Å³)	686.02 (15)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	11.49
Crystal size (mm)	0.32 × 0.22 × 0.20

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Numerical shape of crystal determined optically
T_min, T_max	0.065, 0.108
No. of measured, independent and observed [I > 2σ(I)] reflections	4188, 2390, 2381
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.017, 0.045, 1.18
No. of reflections	2390
No. of parameters	144
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.67

Computer programs: X-AREA (Stoe & Cie, 2005), X-RED (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

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

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1ⁱ	0.90	2.49	2.791 (5)	100.00
N1—H1C···O3	0.90	1.98	2.844 (3)	160.00
N1—H1D···Cl1ⁱⁱ	0.90	2.81	3.540 (4)	139.00
N1—H1D···Cl2ⁱⁱ	0.90	2.49	3.262 (3)	143.00
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) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z.

Acknowledgements

We are grateful to the Islamic Azad University, Shahr-e-Rey Branch, for financial support.

References

Calleja, M., Johnson, K., Belcher, W. J. & Steed, W. (2001). Inorg. Chem. 40, 4978–4985. Web of Science CSD CrossRef PubMed CAS Google Scholar
Chekhlov, A. N. (2000). J. Struct. Chem. 41, 1046–1052. Web of Science CrossRef CAS Google Scholar
Chekhlov, A. N. (2001). Dokl. Akad. Nauk SSSR, 42, 854–859. CAS Google Scholar
Chekhlov, A. N. (2005). Russ. J. Gen. Chem. 75, 1618–1621. Web of Science CrossRef CAS Google Scholar
Chekhlov, A. N. & Martynov, I. V. (1998). Dokl. Akad. Nauk SSSR, 363, 362–366. CAS Google Scholar
Chekhlov, A. N., Yurtanov, A. I. & Martynov, I. V. (1994). Dokl. Akad. Nauk SSSR, 339, 635–640. CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Fonari, M. S., Simonov, Y. A., Chumakov, Y. M., Bocelli, G., Ganin, E. V. & Yavolovskii, A. A. (2004). Supramol. Chem. 16, 23–30. Web of Science CSD CrossRef CAS Google Scholar
Hasan, M., Kozhevnikov, I. V., Siddiqu, M. R. H., Steiner, A. & Winterton, N. (1999). Inorg. Chem. 38, 5637–5641. Web of Science CSD CrossRef CAS Google Scholar
Johnson, K. & Steed, J. W. (1998). Chem. Commun. pp. 1479–1480. Web of Science CSD CrossRef Google Scholar
Moers, O., Henschel, D., Lange, I., Blaschette, A. & Jones, P. G. (2000). Z. Anorg. Allg. Chem. 626, 2388–2398. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Simonov, Y. A., Fonari, M. S., Lipkowski, J., Yavolovskii, A. A. & Ganin, E. V. (2003). J. Incl. Phenom. Macrocycl. Chem. 46, 27–35. Web of Science CSD CrossRef CAS Google Scholar
Stoe & Cie (2005). X-AREA, X-SHAPE and X-RED. Stoe & Cie, Darmstadt, Germany. Google Scholar
Yap, G. P. A., Rheingold, A. R., Das, P. & Crabtree, R. H. (1995). Inorg. Chem. 34, 3474–3476. CSD CrossRef CAS Web of Science Google Scholar
Yousefi, M., Amani, V. & Khavasi, H. R. (2007). Acta Cryst. E63, o3782. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yousefi, M., Teimouri, S., Amani, V. & Khavasi, H. R. (2007). Acta Cryst. E63, m2460–m2461. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, X.-P., Yang, G. & Ng, S. W. (2006). Acta Cryst. E62, m2018–m2020. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages m840-m841

doi:10.1107/S1600536808015353

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

1,4,10,13-Tetra­oxa-7,16-diazo­nia­cyclo­octa­decane bis­­[tetra­chloridoaurate(III)] dihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

1,4,10,13-Tetraoxa-7,16-diazoniacyclooctadecane bis[tetrachloridoaurate(III)] dihydrate