Redetermination of chlorido(2,2′:6′,2′′-terpyridine-κ3N,N′,N′′)gold(I) dichloride trihydrate at 173 K

Friedrich, H.B.; Maguire, G.E.M.; Martincigh, B.S.; McKay, M.G.; Pietersen, L.K.

doi:10.1107/S1600536808027943

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1240

doi:10.1107/S1600536808027943

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ADDENDA AND ERRATA

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Redetermination of chlorido(2,2′:6′,2′′-terpyridine-κ³N,N′,N′′)gold(I) dichloride trihydrate at 173 K

Holger B. Friedrich,^a Glenn E. M. Maguire,^a ^* Bice S. Martincigh,^a Michael G. McKay ^a and Lauren K. Pietersen ^a

^aSchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
^*Correspondence e-mail: maguireg@ukzn.ac.za

(Received 7 July 2008; accepted 1 September 2008; online 6 September 2008)

The redetermined structure of the title compound, [AuCl(C₁₅H₁₁N₃)]Cl₂·3H₂O, at 173 (2) K is reported. The structure displays O—H⋯Cl and O—H⋯O hydrogen bonding. The distance of one of the chloride ions from the gold(I) atom [5.047 (1) Å] differs from that determined previously.

Related literature

For the previous determination of the crystal structure of the title compound, see: Hollis & Lippard (1983 ).

Experimental

Crystal data

[AuCl(C₁₅H₁₁N₃)]Cl₂·3H₂O
M_r = 590.63
Monoclinic, P 2₁ /c
a = 8.4486 (1) Å
b = 6.9766 (1) Å
c = 31.1581 (6) Å
β = 94.392 (1)°
V = 1831.14 (5) Å³
Z = 4
Mo Kα radiation
μ = 8.49 mm⁻¹
T = 173 (2) K
0.41 × 0.31 × 0.30 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: integration [Face-indexed absorption corrections carried out with XPREP (Bruker, 2005 )] T_min = 0.128, T_max = 0.185
13022 measured reflections
4386 independent reflections
4157 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.061
S = 1.37
4386 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 1.32 e Å⁻³
Δρ_min = −2.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯Cl2ⁱ	0.84	2.32	3.140 (4)	167
O1W—H1B⋯Cl3	0.84	2.42	3.229 (4)	161
O2W—H2A⋯Cl2	0.84	2.31	3.141 (4)	172
O2W—H2B⋯O3W	0.84	1.94	2.768 (5)	169
O3W—H3A⋯Cl3ⁱⁱ	0.84	2.31	3.133 (4)	167
O3W—H3B⋯Cl3ⁱⁱⁱ	0.84	2.36	3.194 (4)	171
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-NT (Bruker, 2005); data reduction: SAINT-NT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027943/ez2137sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027943/ez2137Isup2.hkl

checkCIF report

Comment top

The title compound (I, Scheme 1) was synthesized as part of an ongoing study of the DNA binding and intercalation properties of metalloterpyridine complexes.

The asymmetric unit (Fig. 1) consists of the planar terpyridine-AuCl complex with one water molecule and one chloride ion above the plane of the complex, and the remaining two water molecules and a chloride ion below the plane.

A search of the literature revealed that the crystal structure of this compound was previously reported by Hollis & Lippard (1983). The reported structure possesses almost identical crystal parameters to the structure reported here in terms of space group, and unit-cell dimensions and angles. In addition, the coordination sphere parameters appear to closely match those obtained previously. However, the collection of data at 173 K, in comparison to 296 K as reported by Hollis & Lippard, results in some notable conclusions in addition to yielding more accurate data.

The water molecules and chloride ions are involved in extensive intermolecular hydrogen bonding. Fig. 2 illustrates these interactions which extend throughout the crystal structure. The atoms and interaction distances involved in the hydrogen bonding are very similar to those proposed by Hollis & Lippard, and the redetermined hydrogen bonding network confirms the proposed hydrogen bonds.

Additionally, Cl3 is orientated differently here than in the previously determined structure. With reference to the gold centre, Cl3 is found 5.047 (1) Å from the metal atom while the structure reported by Hollis & Lippard shows this distance to be 5.016 Å.

Related literature top

For the previous determination of the crystal structure of the title compound, see: Hollis & Lippard (1983).

Experimental top

A mixture of AuCl₄.3H₂O (0.100 g, 0.29 mmol) and terpyridine (0.072 g, 0.31 mmol) was placed in 10 ml of deionized water in a round-bottom flask. The solution pH was adjusted to 3.0 with 1 M NaOH, and the resulting mixture refluxed at 100°C for 24 h. The red mixture was then cooled to room temperature and filtered to remove small amounts of a purple solid. The filtrate obtained was allowed to stand at room temperature to induce precipitation of the crystalline product. The crystals were filtered off and air-dried to yield the title compound. (0.013 g, 7.5%), mp 503 K. ¹H NMR [DMSO, 600 MHz]: δ = 8.07 (t, 2H), 8.13 (t, 1H), 8.47 (d, 2H), 8.66 (t, 2H), 8.67 (d, 2H), 8.71 (d, 2H). IR (KBr, cm^-1): 3341, 1604, 1584, 1035. ¹³C NMR [DMSO, 150 MHz]: δ = 151.8, 151.5, 146.8, 141.5, 139.7, 126.0, 122.8, 122.7.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of I. Displacement ellipsoids are drawn at the 40% probability level. The labelling of atoms is as shown, and is identical to that of Hollis & Lippard. The two chloride counter ions and the three water molecules associated with I are evident, present above and below the plane of the molecule.
	Fig. 2. Intermolecular hydrogen bonding present in I, shown by the dashed lines. Hanging dashed lines indicate bonding to an adjacent unit cell. Displacement ellipsoids are drawn at the 40% probability level. Protons belonging to individual molecules have been omitted for purposes of clarity. The water and the chloride ions are seen to be found between the individual molecules of I.

Chlorido(2,2':6',2''-terpyridine-κ³N,N',N'')gold(I) dichloride trihydrate top

Crystal data top

[AuCl(C₁₅H₁₁N₃)]Cl₂·3H₂O	F(000) = 1128
M_r = 590.63	D_x = 2.142 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8408 reflections
a = 8.4486 (1) Å	θ = 3.8–28.3°
b = 6.9766 (1) Å	µ = 8.49 mm⁻¹
c = 31.1581 (6) Å	T = 173 K
β = 94.392 (1)°	Block, brown
V = 1831.14 (5) Å³	0.41 × 0.31 × 0.30 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	4386 independent reflections
Radiation source: fine-focus sealed tube	4157 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 28.0°, θ_min = 3.5°
Absorption correction: integration [Face-indexed absorption corrections carried out with XPREP (Bruker, 2005)]	h = −11→11
T_min = 0.128, T_max = 0.185	k = −9→8
13022 measured reflections	l = −41→39

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.061	H-atom parameters constrained
S = 1.37	w = 1/[σ²(F_o²) + (0.0093P)² + 4.719P] where P = (F_o² + 2F_c²)/3
4386 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 1.32 e Å⁻³
0 restraints	Δρ_min = −2.24 e Å⁻³

Crystal data top

[AuCl(C₁₅H₁₁N₃)]Cl₂·3H₂O	V = 1831.14 (5) Å³
M_r = 590.63	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.4486 (1) Å	µ = 8.49 mm⁻¹
b = 6.9766 (1) Å	T = 173 K
c = 31.1581 (6) Å	0.41 × 0.31 × 0.30 mm
β = 94.392 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4386 independent reflections
Absorption correction: integration [Face-indexed absorption corrections carried out with XPREP (Bruker, 2005)]	4157 reflections with I > 2σ(I)
T_min = 0.128, T_max = 0.185	R_int = 0.034
13022 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.061	H-atom parameters constrained
S = 1.37	Δρ_max = 1.32 e Å⁻³
4386 reflections	Δρ_min = −2.24 e Å⁻³
226 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	−0.0770 (6)	0.2047 (7)	0.02507 (15)	0.0253 (10)
H1	−0.0237	0.2331	0.0001	0.030*
C2	−0.2269 (6)	0.1252 (7)	0.02079 (17)	0.0298 (11)
H2	−0.2766	0.0986	−0.0069	0.036*
C3	−0.3033 (6)	0.0848 (7)	0.05707 (17)	0.0298 (11)
H3	−0.4064	0.0297	0.0545	0.036*
C4	−0.2298 (5)	0.1246 (7)	0.09735 (16)	0.0248 (10)
H4	−0.2823	0.0976	0.1225	0.030*
C5	−0.0803 (5)	0.2036 (6)	0.10059 (15)	0.0204 (9)
C6	0.0097 (5)	0.2552 (6)	0.14095 (14)	0.0196 (9)
C7	−0.0305 (5)	0.2284 (7)	0.18273 (15)	0.0261 (10)
H7	−0.1293	0.1721	0.1882	0.031*
C8	0.0750 (6)	0.2845 (8)	0.21643 (16)	0.0290 (11)
H8	0.0478	0.2669	0.2452	0.035*
C9	0.2201 (6)	0.3663 (7)	0.20891 (15)	0.0265 (10)
H9	0.2926	0.4037	0.2322	0.032*
C10	0.2570 (5)	0.3922 (6)	0.16673 (15)	0.0203 (9)
C11	0.4020 (5)	0.4747 (6)	0.15124 (15)	0.0209 (9)
C12	0.5251 (5)	0.5513 (7)	0.17706 (17)	0.0272 (10)
H12	0.5194	0.5570	0.2074	0.033*
C13	0.6570 (5)	0.6197 (7)	0.15853 (18)	0.0305 (11)
H13	0.7427	0.6729	0.1762	0.037*
C14	0.6651 (5)	0.6113 (7)	0.11450 (18)	0.0287 (11)
H14	0.7564	0.6564	0.1016	0.034*
C15	0.5375 (5)	0.5358 (7)	0.08946 (17)	0.0250 (10)
H15	0.5408	0.5313	0.0591	0.030*
Cl1	0.28844 (15)	0.3714 (2)	0.00827 (4)	0.0321 (3)
Cl2	0.06873 (13)	0.75596 (17)	0.08334 (4)	0.0268 (2)
Cl3	0.56001 (14)	0.06210 (19)	0.19728 (4)	0.0298 (3)
Au1	0.211462 (19)	0.35966 (2)	0.076389 (5)	0.01864 (6)
N1	−0.0062 (4)	0.2421 (5)	0.06372 (12)	0.0206 (8)
N2	0.1517 (4)	0.3343 (5)	0.13536 (11)	0.0162 (7)
N3	0.4098 (4)	0.4693 (5)	0.10746 (12)	0.0200 (8)
O1W	0.3810 (4)	−0.0056 (6)	0.10320 (13)	0.0384 (9)
H1A	0.3000	−0.0750	0.1021	0.058*
H1B	0.4060	0.0050	0.1296	0.058*
O2W	0.0068 (4)	0.7688 (7)	0.18143 (12)	0.0422 (10)
H2A	0.0261	0.7780	0.1555	0.063*
H2B	0.0931	0.7980	0.1949	0.063*
O3W	0.2720 (4)	0.8576 (6)	0.23548 (13)	0.0449 (10)
H3A	0.3421	0.9059	0.2213	0.067*
H3B	0.3221	0.7749	0.2508	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.027 (2)	0.028 (3)	0.021 (2)	−0.0037 (19)	0.0037 (18)	0.002 (2)
C2	0.028 (2)	0.028 (3)	0.033 (3)	−0.006 (2)	−0.003 (2)	−0.004 (2)
C3	0.024 (2)	0.026 (3)	0.039 (3)	−0.0032 (19)	0.002 (2)	−0.002 (2)
C4	0.021 (2)	0.021 (2)	0.033 (3)	−0.0039 (18)	0.0076 (18)	−0.001 (2)
C5	0.021 (2)	0.015 (2)	0.025 (2)	0.0008 (16)	0.0039 (17)	0.0019 (18)
C6	0.0170 (19)	0.017 (2)	0.026 (2)	0.0012 (16)	0.0065 (17)	0.0039 (18)
C7	0.024 (2)	0.030 (3)	0.025 (2)	−0.0022 (19)	0.0101 (19)	0.001 (2)
C8	0.033 (3)	0.035 (3)	0.019 (2)	0.001 (2)	0.0074 (19)	0.002 (2)
C9	0.027 (2)	0.031 (3)	0.021 (2)	0.002 (2)	0.0013 (18)	−0.001 (2)
C10	0.021 (2)	0.016 (2)	0.024 (2)	0.0010 (16)	0.0032 (17)	0.0017 (18)
C11	0.020 (2)	0.018 (2)	0.025 (2)	0.0020 (16)	0.0048 (17)	0.0004 (18)
C12	0.023 (2)	0.026 (3)	0.032 (3)	0.0007 (19)	−0.0009 (19)	0.000 (2)
C13	0.018 (2)	0.024 (3)	0.049 (3)	−0.0013 (18)	−0.001 (2)	−0.001 (2)
C14	0.018 (2)	0.020 (3)	0.048 (3)	−0.0018 (17)	0.008 (2)	0.001 (2)
C15	0.022 (2)	0.021 (2)	0.033 (3)	−0.0013 (18)	0.0076 (19)	0.001 (2)
Cl1	0.0363 (6)	0.0386 (7)	0.0230 (6)	−0.0093 (5)	0.0120 (5)	−0.0003 (5)
Cl2	0.0285 (5)	0.0258 (6)	0.0260 (6)	0.0037 (4)	0.0015 (4)	0.0004 (5)
Cl3	0.0263 (5)	0.0290 (6)	0.0344 (6)	−0.0015 (5)	0.0044 (5)	0.0023 (5)
Au1	0.01834 (8)	0.01925 (9)	0.01896 (9)	−0.00206 (7)	0.00558 (6)	0.00098 (7)
N1	0.0188 (17)	0.019 (2)	0.024 (2)	−0.0018 (14)	0.0045 (15)	0.0004 (16)
N2	0.0180 (16)	0.0136 (18)	0.0175 (17)	0.0029 (13)	0.0040 (13)	0.0000 (14)
N3	0.0181 (17)	0.0163 (19)	0.026 (2)	−0.0003 (14)	0.0027 (15)	0.0003 (16)
O1W	0.0303 (19)	0.043 (2)	0.042 (2)	−0.0015 (17)	0.0029 (16)	0.0090 (19)
O2W	0.0289 (18)	0.068 (3)	0.030 (2)	−0.0122 (19)	0.0052 (15)	−0.003 (2)
O3W	0.0305 (19)	0.061 (3)	0.042 (2)	−0.0077 (19)	−0.0007 (17)	0.013 (2)

Geometric parameters (Å, º) top

C1—N1	1.329 (6)	C11—N3	1.371 (6)
C1—C2	1.380 (6)	C11—C12	1.373 (7)
C1—H1	0.9500	C12—C13	1.379 (7)
C2—C3	1.373 (7)	C12—H12	0.9500
C2—H2	0.9500	C13—C14	1.380 (8)
C3—C4	1.385 (7)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.386 (7)
C4—C5	1.375 (6)	C14—H14	0.9500
C4—H4	0.9500	C15—N3	1.336 (5)
C5—N1	1.376 (6)	C15—H15	0.9500
C5—C6	1.463 (6)	Cl1—Au1	2.2686 (11)
C6—N2	1.345 (5)	Au1—N2	1.950 (3)
C6—C7	1.383 (6)	Au1—N3	2.021 (4)
C7—C8	1.381 (7)	Au1—N1	2.025 (4)
C7—H7	0.9500	O1W—H1A	0.8369
C8—C9	1.388 (7)	O1W—H1B	0.8373
C8—H8	0.9500	O2W—H2A	0.8388
C9—C10	1.386 (6)	O2W—H2B	0.8381
C9—H9	0.9500	O3W—H3A	0.8361
C10—N2	1.333 (6)	O3W—H3B	0.8423
C10—C11	1.468 (6)

N1—C1—C2	120.8 (4)	C12—C11—C10	125.0 (4)
N1—C1—H1	119.6	C11—C12—C13	119.3 (5)
C2—C1—H1	119.6	C11—C12—H12	120.3
C3—C2—C1	119.3 (5)	C13—C12—H12	120.3
C3—C2—H2	120.4	C12—C13—C14	120.3 (5)
C1—C2—H2	120.4	C12—C13—H13	119.8
C2—C3—C4	119.9 (5)	C14—C13—H13	119.8
C2—C3—H3	120.1	C13—C14—C15	118.7 (4)
C4—C3—H3	120.1	C13—C14—H14	120.7
C5—C4—C3	119.5 (4)	C15—C14—H14	120.7
C5—C4—H4	120.2	N3—C15—C14	120.9 (5)
C3—C4—H4	120.2	N3—C15—H15	119.5
C4—C5—N1	119.4 (4)	C14—C15—H15	119.5
C4—C5—C6	125.1 (4)	N2—Au1—N3	81.25 (15)
N1—C5—C6	115.5 (4)	N2—Au1—N1	81.39 (15)
N2—C6—C7	117.6 (4)	N3—Au1—N1	162.64 (15)
N2—C6—C5	113.6 (4)	N2—Au1—Cl1	176.48 (11)
C7—C6—C5	128.9 (4)	N3—Au1—Cl1	98.51 (11)
C8—C7—C6	119.2 (4)	N1—Au1—Cl1	98.82 (11)
C8—C7—H7	120.4	C1—N1—C5	121.1 (4)
C6—C7—H7	120.4	C1—N1—Au1	126.5 (3)
C7—C8—C9	121.0 (4)	C5—N1—Au1	112.4 (3)
C7—C8—H8	119.5	C10—N2—C6	125.6 (4)
C9—C8—H8	119.5	C10—N2—Au1	117.2 (3)
C10—C9—C8	118.7 (4)	C6—N2—Au1	117.2 (3)
C10—C9—H9	120.7	C15—N3—C11	120.7 (4)
C8—C9—H9	120.7	C15—N3—Au1	126.7 (3)
N2—C10—C9	118.0 (4)	C11—N3—Au1	112.7 (3)
N2—C10—C11	113.9 (4)	H1A—O1W—H1B	103.6
C9—C10—C11	128.1 (4)	H2A—O2W—H2B	103.8
N3—C11—C12	120.1 (4)	H3A—O3W—H3B	103.3
N3—C11—C10	114.9 (4)

N1—C1—C2—C3	0.1 (8)	N2—Au1—N1—C1	178.4 (4)
C1—C2—C3—C4	0.2 (8)	N3—Au1—N1—C1	178.2 (4)
C2—C3—C4—C5	−0.3 (7)	Cl1—Au1—N1—C1	−5.1 (4)
C3—C4—C5—N1	0.1 (7)	N2—Au1—N1—C5	−0.9 (3)
C3—C4—C5—C6	179.1 (4)	N3—Au1—N1—C5	−1.1 (7)
C4—C5—C6—N2	−178.5 (4)	Cl1—Au1—N1—C5	175.6 (3)
N1—C5—C6—N2	0.5 (6)	C9—C10—N2—C6	1.3 (7)
C4—C5—C6—C7	3.4 (8)	C11—C10—N2—C6	−179.6 (4)
N1—C5—C6—C7	−177.6 (5)	C9—C10—N2—Au1	−176.8 (3)
N2—C6—C7—C8	0.5 (7)	C11—C10—N2—Au1	2.3 (5)
C5—C6—C7—C8	178.5 (5)	C7—C6—N2—C10	−1.1 (7)
C6—C7—C8—C9	−0.2 (8)	C5—C6—N2—C10	−179.4 (4)
C7—C8—C9—C10	0.5 (8)	C7—C6—N2—Au1	177.0 (3)
C8—C9—C10—N2	−1.0 (7)	C5—C6—N2—Au1	−1.3 (5)
C8—C9—C10—C11	−179.9 (5)	N3—Au1—N2—C10	−0.6 (3)
N2—C10—C11—N3	−3.5 (6)	N1—Au1—N2—C10	179.5 (3)
C9—C10—C11—N3	175.5 (4)	N3—Au1—N2—C6	−178.9 (3)
N2—C10—C11—C12	177.3 (4)	N1—Au1—N2—C6	1.2 (3)
C9—C10—C11—C12	−3.7 (8)	C14—C15—N3—C11	0.2 (7)
N3—C11—C12—C13	−0.9 (7)	C14—C15—N3—Au1	178.7 (3)
C10—C11—C12—C13	178.2 (4)	C12—C11—N3—C15	0.9 (7)
C11—C12—C13—C14	0.0 (7)	C10—C11—N3—C15	−178.4 (4)
C12—C13—C14—C15	1.0 (7)	C12—C11—N3—Au1	−177.8 (4)
C13—C14—C15—N3	−1.1 (7)	C10—C11—N3—Au1	2.9 (5)
C2—C1—N1—C5	−0.3 (7)	N2—Au1—N3—C15	−179.9 (4)
C2—C1—N1—Au1	−179.6 (4)	N1—Au1—N3—C15	−179.7 (4)
C4—C5—N1—C1	0.2 (7)	Cl1—Au1—N3—C15	3.6 (4)
C6—C5—N1—C1	−178.9 (4)	N2—Au1—N3—C11	−1.4 (3)
C4—C5—N1—Au1	179.5 (3)	N1—Au1—N3—C11	−1.1 (7)
C6—C5—N1—Au1	0.5 (5)	Cl1—Au1—N3—C11	−177.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···Cl2ⁱ	0.84	2.32	3.140 (4)	167
O1W—H1B···Cl3	0.84	2.42	3.229 (4)	161
O2W—H2A···Cl2	0.84	2.31	3.141 (4)	172
O2W—H2B···O3W	0.84	1.94	2.768 (5)	169
O3W—H3A···Cl3ⁱⁱ	0.84	2.31	3.133 (4)	167
O3W—H3B···Cl3ⁱⁱⁱ	0.84	2.36	3.194 (4)	171

Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[AuCl(C₁₅H₁₁N₃)]Cl₂·3H₂O
M_r	590.63
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	8.4486 (1), 6.9766 (1), 31.1581 (6)
β (°)	94.392 (1)
V (Å³)	1831.14 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	8.49
Crystal size (mm)	0.41 × 0.31 × 0.30

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Integration [Face-indexed absorption corrections carried out with XPREP (Bruker, 2005)]
T_min, T_max	0.128, 0.185
No. of measured, independent and observed [I > 2σ(I)] reflections	13022, 4386, 4157
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.061, 1.37
No. of reflections	4386
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.32, −2.24

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···Cl2ⁱ	0.84	2.32	3.140 (4)	167
O1W—H1B···Cl3	0.84	2.42	3.229 (4)	161
O2W—H2A···Cl2	0.84	2.31	3.141 (4)	172
O2W—H2B···O3W	0.84	1.94	2.768 (5)	169
O3W—H3A···Cl3ⁱⁱ	0.84	2.31	3.133 (4)	167
O3W—H3B···Cl3ⁱⁱⁱ	0.84	2.36	3.194 (4)	171

Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) −x+1, y+1/2, −z+1/2.

Acknowledgements

We thank Dr Manuel Fernandes of the Jan Boeyens Structural Chemistry Laboratory at the University of the Witwatersrand for his assistance in the acquisition and solution of the crystallographic data.

References

Bruker (2005). APEX2 and SAINT-NT (includes XPREP and SADABS). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hollis, L. S. & Lippard, S. J. (1983). J. Am. Chem. Soc. 105, 4293–4299. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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