Literature DB >> 21582047

1,3-Benzothia-zolium tetra-chlorido-aurate(III) tetra-hydro-furan solvate.

Tesfamariam K Hagos¹, Stefan D Nogai, Liliana Dobrzańska, Stephanie Cronje, Helgard G Raubenheimer.

Abstract

In the crystal structure of the title ionic compound (C(7)H(6)NS)[AuCl(4)]·C(4)H(8)O, the [AuCl(4)](-) anion shows a typical square-planar geometry. Numerous weak C-H⋯Cl hydrogen bonds between [AuCl(4)](-) and the 1,3-benzothia-zolium units form layers comprised of 24-membered rings in which hydrogen-bonded tetra-hydro-furan (THF) solvent mol-ecules are accommodated. C-H⋯Cl inter-actions between THF and [AuCl(4)](-) from adjacent layers result in bilayers. These are further stabilized by π-π inter-actions between the thia-zole and benzene rings [centroid-centroid distance = 3.971 (3) Å], resulting in the formation of a three-dimensional supra-molecular assembly.

Entities: CellLine Chemical Disease Gene Species

Year: 2009 PMID： 21582047 PMCID： PMC2968643 DOI： 10.1107/S1600536809003572

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For background, see: Hagos et al. (2008 ▶). For related compounds, see: Huynh et al. (2006 ▶); Yen et al. (2006 ▶, 2008 ▶). For bond-length data, see Adé et al. (2004 ▶); Asaji et al. (2004 ▶); Makotchenko et al. (2006 ▶). For related literature, see: Brammer et al. (2001 ▶).

Experimental

Crystal data

(C7H6NS)[AuCl4]·C4H8O M = 547.06 Triclinic, a = 7.3213 (7) Å b = 10.3498 (10) Å c = 11.8783 (12) Å α = 99.331 (1)° β = 107.579 (1)° γ = 104.483 (2)° V = 802.75 (14) Å3 Z = 2 Mo Kα radiation μ = 9.95 mm−1 T = 100 (2) K 0.30 × 0.20 × 0.10 mm

Data collection

Bruker APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.101, T max = 0.371 4957 measured reflections 3504 independent reflections 3325 reflections with I > 2σ(I) R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.027 wR(F 2) = 0.064 S = 1.05 3504 reflections 175 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 2.27 e Å−3 Δρmin = −1.00 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour 2001 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003572/ng2541sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003572/ng2541Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C₇H₆NS)[AuCl₄]·C₄H₈O	Z = 2
M_r = 547.06	F(000) = 516
Triclinic, P1	D_x = 2.263 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3213 (7) Å	Cell parameters from 3347 reflections
b = 10.3498 (10) Å	θ = 2.4–28.1°
c = 11.8783 (12) Å	µ = 9.95 mm⁻¹
α = 99.331 (1)°	T = 100 K
β = 107.579 (1)°	Block, orange
γ = 104.483 (2)°	0.30 × 0.20 × 0.10 mm
V = 802.75 (14) Å³

Bruker APEX CCD area-detector diffractometer	3504 independent reflections
Radiation source: fine-focus sealed tube	3325 reflections with I > 2σ(I)
graphite	R_int = 0.013
ω scans	θ_max = 28.3°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −9→9
T_min = 0.101, T_max = 0.371	k = −13→13
4957 measured reflections	l = −14→15

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0432P)² + 0.5801P] where P = (F_o² + 2F_c²)/3
3504 reflections	(Δ/σ)_max < 0.001
175 parameters	Δρ_max = 2.27 e Å⁻³
1 restraint	Δρ_min = −1.00 e Å⁻³

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	U_iso*/U_eq
Au1	0.00874 (2)	0.215338 (16)	0.234396 (14)	0.01707 (7)
Cl1	0.03040 (19)	−0.00191 (12)	0.22763 (11)	0.0318 (3)
Cl2	−0.26390 (17)	0.12764 (11)	0.05577 (10)	0.0235 (2)
Cl3	−0.00788 (18)	0.43396 (11)	0.24088 (10)	0.0249 (2)
Cl4	0.27948 (17)	0.29983 (13)	0.41246 (10)	0.0287 (2)
C5	0.6777 (7)	0.7714 (5)	0.9404 (4)	0.0215 (9)
H5	0.6992	0.8678	0.9629	0.026*
N6	0.5448 (6)	0.6896 (4)	0.8362 (3)	0.0207 (8)
H6	0.477 (7)	0.718 (5)	0.778 (4)	0.025*
C7	0.5351 (7)	0.5514 (4)	0.8204 (4)	0.0178 (8)
C8	0.4115 (7)	0.4415 (5)	0.7204 (4)	0.0233 (9)
H8	0.3166	0.4541	0.6517	0.028*
C9	0.4313 (8)	0.3142 (5)	0.7244 (4)	0.0276 (10)
H9	0.3487	0.2370	0.6571	0.033*
C10	0.5711 (8)	0.2954 (5)	0.8257 (5)	0.0276 (10)
H10	0.5811	0.2056	0.8254	0.033*
C11	0.6940 (7)	0.4035 (5)	0.9253 (4)	0.0231 (9)
H11	0.7888	0.3903	0.9936	0.028*
C12	0.6738 (6)	0.5330 (4)	0.9220 (4)	0.0182 (8)
S13	0.80728 (17)	0.68998 (12)	1.03100 (10)	0.0219 (2)
O14	0.3180 (5)	0.7755 (3)	0.6536 (3)	0.0219 (7)
C15	0.3808 (7)	0.9178 (5)	0.6497 (4)	0.0227 (9)
H15B	0.5216	0.9468	0.6520	0.027*
H15A	0.3715	0.9791	0.7195	0.027*
C16	0.2358 (8)	0.9226 (5)	0.5300 (5)	0.0286 (10)
H16B	0.2955	1.0014	0.5009	0.034*
H16A	0.1068	0.9286	0.5372	0.034*
C17	0.2060 (9)	0.7850 (5)	0.4458 (5)	0.0335 (12)
H17A	0.0746	0.7534	0.3772	0.040*
H17B	0.3159	0.7918	0.4127	0.040*
C18	0.2116 (7)	0.6889 (5)	0.5298 (4)	0.0241 (9)
H18B	0.0726	0.6352	0.5198	0.029*
H18A	0.2830	0.6236	0.5108	0.029*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au1	0.01437 (9)	0.01940 (10)	0.01510 (9)	0.00527 (6)	0.00270 (6)	0.00332 (6)
Cl1	0.0340 (7)	0.0253 (6)	0.0289 (6)	0.0156 (5)	−0.0022 (5)	0.0042 (5)
Cl2	0.0220 (5)	0.0200 (5)	0.0205 (5)	0.0076 (4)	−0.0028 (4)	0.0022 (4)
Cl3	0.0284 (6)	0.0196 (5)	0.0221 (5)	0.0062 (4)	0.0045 (4)	0.0038 (4)
Cl4	0.0211 (5)	0.0370 (6)	0.0194 (5)	0.0097 (5)	−0.0013 (4)	0.0004 (5)
C5	0.025 (2)	0.019 (2)	0.023 (2)	0.0104 (18)	0.0086 (19)	0.0063 (18)
N6	0.0214 (19)	0.0210 (19)	0.0190 (18)	0.0094 (16)	0.0037 (15)	0.0059 (15)
C7	0.017 (2)	0.020 (2)	0.016 (2)	0.0064 (17)	0.0048 (17)	0.0062 (17)
C8	0.024 (2)	0.025 (2)	0.015 (2)	0.0063 (19)	0.0024 (18)	0.0030 (18)
C9	0.034 (3)	0.020 (2)	0.020 (2)	0.007 (2)	0.002 (2)	−0.0006 (18)
C10	0.034 (3)	0.021 (2)	0.026 (2)	0.013 (2)	0.005 (2)	0.0068 (19)
C11	0.025 (2)	0.021 (2)	0.022 (2)	0.0102 (19)	0.0023 (18)	0.0085 (18)
C12	0.014 (2)	0.020 (2)	0.017 (2)	0.0045 (17)	0.0016 (16)	0.0039 (17)
S13	0.0206 (5)	0.0221 (5)	0.0177 (5)	0.0071 (4)	0.0009 (4)	0.0025 (4)
O14	0.0250 (17)	0.0173 (15)	0.0198 (16)	0.0060 (13)	0.0031 (13)	0.0058 (12)
C15	0.025 (2)	0.020 (2)	0.024 (2)	0.0075 (19)	0.0089 (19)	0.0080 (18)
C16	0.035 (3)	0.025 (2)	0.028 (3)	0.013 (2)	0.009 (2)	0.010 (2)
C17	0.041 (3)	0.027 (3)	0.025 (3)	0.007 (2)	0.005 (2)	0.007 (2)
C18	0.023 (2)	0.025 (2)	0.020 (2)	0.0081 (19)	0.0012 (18)	0.0032 (18)

Au1—Cl4	2.2733 (11)	C11—C12	1.390 (6)
Au1—Cl1	2.2835 (12)	C11—H11	0.9500
Au1—Cl2	2.2850 (11)	C12—S13	1.741 (4)
Au1—Cl3	2.2864 (11)	O14—C15	1.443 (5)
C5—N6	1.310 (6)	O14—C18	1.450 (5)
C5—S13	1.686 (4)	C15—C16	1.513 (6)
C5—H5	0.9500	C15—H15B	0.9900
N6—C7	1.392 (6)	C15—H15A	0.9900
N6—H6	0.86 (5)	C16—C17	1.525 (7)
C7—C8	1.387 (6)	C16—H16B	0.9900
C7—C12	1.398 (6)	C16—H16A	0.9900
C8—C9	1.368 (7)	C17—C18	1.518 (7)
C8—H8	0.9500	C17—H17A	0.9900
C9—C10	1.402 (7)	C17—H17B	0.9900
C9—H9	0.9500	C18—H18B	0.9900
C10—C11	1.373 (7)	C18—H18A	0.9900
C10—H10	0.9500

Cl4—Au1—Cl1	90.14 (4)	C11—C12—S13	128.7 (3)
Cl4—Au1—Cl2	179.27 (4)	C7—C12—S13	110.4 (3)
Cl1—Au1—Cl2	89.16 (4)	C5—S13—C12	90.5 (2)
Cl4—Au1—Cl3	89.45 (4)	C15—O14—C18	109.0 (3)
Cl1—Au1—Cl3	179.07 (4)	O14—C15—C16	104.8 (4)
Cl2—Au1—Cl3	91.25 (4)	O14—C15—H15B	110.8
N6—C5—S13	114.0 (3)	C16—C15—H15B	110.8
N6—C5—H5	123.0	O14—C15—H15A	110.8
S13—C5—H5	123.0	C16—C15—H15A	110.8
C5—N6—C7	114.4 (4)	H15B—C15—H15A	108.9
C5—N6—H6	124 (4)	C15—C16—C17	101.8 (4)
C7—N6—H6	121 (4)	C15—C16—H16B	111.4
C8—C7—N6	127.8 (4)	C17—C16—H16B	111.4
C8—C7—C12	121.4 (4)	C15—C16—H16A	111.4
N6—C7—C12	110.8 (4)	C17—C16—H16A	111.4
C9—C8—C7	117.5 (4)	H16B—C16—H16A	109.3
C9—C8—H8	121.3	C18—C17—C16	102.9 (4)
C7—C8—H8	121.3	C18—C17—H17A	111.2
C8—C9—C10	121.4 (5)	C16—C17—H17A	111.2
C8—C9—H9	119.3	C18—C17—H17B	111.2
C10—C9—H9	119.3	C16—C17—H17B	111.2
C11—C10—C9	121.7 (4)	H17A—C17—H17B	109.1
C11—C10—H10	119.2	O14—C18—C17	106.7 (4)
C9—C10—H10	119.2	O14—C18—H18B	110.4
C10—C11—C12	117.2 (4)	C17—C18—H18B	110.4
C10—C11—H11	121.4	O14—C18—H18A	110.4
C12—C11—H11	121.4	C17—C18—H18A	110.4
C11—C12—C7	120.9 (4)	H18B—C18—H18A	108.6

S13—C5—N6—C7	0.3 (5)	N6—C7—C12—C11	−178.5 (4)
C5—N6—C7—C8	−179.6 (5)	C8—C7—C12—S13	179.4 (4)
C5—N6—C7—C12	−0.3 (5)	N6—C7—C12—S13	0.1 (5)
N6—C7—C8—C9	178.7 (5)	N6—C5—S13—C12	−0.2 (4)
C12—C7—C8—C9	−0.5 (7)	C11—C12—S13—C5	178.6 (4)
C7—C8—C9—C10	0.0 (8)	C7—C12—S13—C5	0.0 (4)
C8—C9—C10—C11	0.1 (9)	C18—O14—C15—C16	24.2 (5)
C9—C10—C11—C12	0.2 (8)	O14—C15—C16—C17	−37.1 (5)
C10—C11—C12—C7	−0.6 (7)	C15—C16—C17—C18	35.6 (5)
C10—C11—C12—S13	−179.0 (4)	C15—O14—C18—C17	−1.1 (5)
C8—C7—C12—C11	0.8 (7)	C16—C17—C18—O14	−22.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O14	0.86 (5)	1.87 (5)	2.728 (5)	177 (6)
C5—H5···Cl2ⁱ	0.95	2.65	3.588 (5)	170
C8—H8···Cl4	0.95	2.93	3.447 (5)	116
C9—H9···Cl4	0.95	3.00	3.498 (5)	114
C10—H10···Cl2ⁱⁱ	0.95	2.96	3.541 (6)	121
C11—H11···Cl2ⁱⁱ	0.95	2.90	3.498 (5)	122
C11—H11···Cl3ⁱⁱ	0.95	2.77	3.639 (5)	154
C15—H15B···Cl1ⁱⁱⁱ	0.99	3.02	3.922 (6)	153
C18—H18A···Cl4ⁱⁱⁱ	0.99	2.91	3.547 (6)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯O14	0.86 (5)	1.87 (5)	2.728 (5)	177 (6)
C5—H5⋯Cl2ⁱ	0.95	2.65	3.588 (5)	170
C8—H8⋯Cl4	0.95	2.93	3.447 (5)	116
C9—H9⋯Cl4	0.95	3.00	3.498 (5)	114
C10—H10⋯Cl2ⁱⁱ	0.95	2.96	3.541 (6)	121
C11—H11⋯Cl2ⁱⁱ	0.95	2.90	3.498 (5)	122
C11—H11⋯Cl3ⁱⁱ	0.95	2.77	3.639 (5)	154
C15—H15B⋯Cl1ⁱⁱⁱ	0.99	3.02	3.922 (6)	153
C18—H18A⋯Cl4ⁱⁱⁱ	0.99	2.91	3.547 (6)	123

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

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