The hydrated and anhydrous gold(III) tetra­chloride salts of L-ecgonine, an important forensic toxicology marker for cocaine

The structure of the hydrated gold(III) tetra­chloride salt of L-ecgonine {hydronium tetra­kis[(1R,2R,3S,5S,8S)-3-hydr­oxy-8-methyl-8-azoniabicyclo­[3.2.1]octane-2-carboxyl­ate penta­kis[tetra­chloridoaurate(III)] hexa­hydrate}, (C₉H₁₆NO₃)₄(H₃O)[AuCl₄]₅·6H₂O, demonstrates an unprecedented stoichiometric relationship between the cations and anions in the unit cell. The previous tropane alkaloid structures, including the related hydro­chloride salts, all have a cation-anion ratio of 1:1, as does the anhydrous salt described here, namely (1R,2R,3S,5S,8S)-3-hydr­oxy-8-methyl-8-azoniabicyclo­[3.2.1]octane-2-carboxyl­ate tetra­chloridoaurate(III), (C₉H₁₆NO₃)[AuCl₄]. The hydrated salt, however, consists of four mono­positive N-protonated units of the alkaloid and five [AuCl₄]^- counter-ions, plus seven solvent water mol­ecules. The H atom required for change balance has been assigned to a water molecule. In addition, the hydrate has a novel arrangement, with all seven of the water mol­ecules and all of the O atoms in the cations participating in an alternating arrangement of inter­leaved sheets of the anionic species. Both the hydrate and the anhydrous salt of the same toxicologically important marker for cocaine show that the cation and anion are in close proximity to each other, as was found in the gold(III) tetra­chloride salt of L-cocaine.

S1. Comment

L-Ecgonine and L-cocaine are among 22 naturally occurring alkaloids found in the leaves of the coca plant, Erythroxylum coca (Ensing & Hummelen, 1991). L-Ecgonine (C₉H₁₅NO₃), a nitrogen-bridged bicyclo[3.2.1]octane, is both a precursor and a human metabolite of L-cocaine. It is the hydroxy acid obtained by complete acidic, alkaline or enzymatic hydrolysis of both ester functions in L-cocaine, and can crystallize as the hydrochloride salt (Wood et al., 2008). During in vitro storage of blood, cocaine can undergo selective monohydrolysis via two mechanisms: partial saponification under alkaline conditions to yield benzoylecgonine, or enzymatic hydrolysis catalyzed by pseudocholinesterase to yield methylecgonine (ecgonine methyl ester) (Isenschmid et al., 1989). Both of these breakdown products can degrade further to a common stable product, L-ecgonine (Klingmann et al., 2001), which is consistently observed in post mortem blood specimens and whole-blood specimens of cocaine addicts, thus demonstrating the utility of L-ecgonine as a stable marker for recent cocaine use (Logan, 2001). Because time, temperature, drug concentration and the presence of preservative agents can all affect the stability of cocaine in blood and plasma (Baselt, 1983), L-ecgonine, the fully hydrolyzed degradation product, is a much better marker for cocaine use than either benzoylecgonine or ecgonine methyl ester.

The use of the gold(III) chloride microcrystal test in the identification and differentiation of L-cocaine from its seven stereoisomers (Allen et al., 1981) and similar related structures, i.e. L-ecgonine (Amelink, 1938), has been described by the current authors in a previous paper (Wood et al., 2007).

In studying the three-dimensional structures of several cocaine derivatives, the authors have previously reported those of the gold(III) tetrachloride salt of L-cocaine (Wood et al., 2007) and of the hydrochloride salt of L-ecgonine (Wood et al., 2008). We report here the structures of the gold(III) tetrachloride salt of L-ecgonine, which exists as both the hydrate form, (I), (C₉H₁₆NO₃)₄(H₃O)[AuCl₄]₅.6H₂O, and the anhydrous form, (II), (C₉H₁₆NO₃)[AuCl₄].

The asymmetric unit of (I) contains four monopositive N-protonated L-ecgonine cations surrounded by five [AuCl₄]^- anions. One of the seven water molecules has to be a hydronium ion or one of the hydroxy groups of the cations has to be diprotonated, for charge balance. However, the additional proton was not found and we have no evidence as to whether it is consistently positioned in the structure. Each of the four L-ecgonine cations has its quaternary N-bound H atom intramolecularly hydrogen-bonded to its carboxyl C═O group (Table 2, entries 1–4), as was found in (-)-norcocaine [N···O = 2.306 (2) Å; Zhu et al., 1994], in the tetrachloroaurate(III) salt of L-cocaine [N···O = 2.756 (6) Å; Wood et al., 2007] and in the hydrochloride salt of L-ecgonine [N···O = 2.7608 (17) Å; Wood et al., 2008]. All of the L-ecgonine cations in (I) have ordered carboxyl groups, except for molecule B where C9B—O1B = 1.260 (13) and C9B—O2B = 1.280 (14) Å. As a result of this disorder, the acid H atom of this cation could not be found.

Four of the five [AuCl₄]^- anions of (I) exhibit square-planar geometry, with mean deviations from the five-atom plane ranging from 0.006 (3) (for the Au3 anion) to 0.013 (2) Å (for the Au4 anion). The fifth anion (containing Au1) has a mean deviation from the plane of 0.048 (3) Å, with the Au^III center 0.0070 (11) Å above the best plane. In this anion, one trans pair of Cl atoms is above the best plane by 0.051 (2) Å and the other pair below the plane by 0.054 (2) Å. In a search of the Cambridge Structural Database (CSD, Version 5.29, update of 2008; Allen, 2002), 106 structures containing the gold(III) tetrachloride anion were found, several containing multiple [AuCl₄]^- species, for a total of 136 different anions. Of these, 71 are essentially flat, and the rest have varying degrees of bowing of the square-planar arrangement of the [AuCl₄]^- moiety. Only three show flexing larger than that found in (I): tetra(methylthio)tetrathiafulvalene bis(tetrachloroaurate) (refcode GEHSOB01; Jones, 1989), the gold(III) tetrachloride salt of L-cocaine (refcode SETLOT; Wood et al., 2007) and N-benzyl-N,N-bis(pyridinium-2-ylmethyl)amine chloride tetrachloroaurate(III) (refcode NIBWEB; Cao et al., 2007).

Within the asymmetric unit of (I) there are three close Cl···O distances (Table 1), two of which involve water molecules and are 0.05–0.06 Å less than the relevant van der Waals sum of 3.27 Å [Standard reference?], while the third is proximal to the acid carbonyl of an L-ecgonine cation and is shorter than the van der Waals distance by 0.12 Å. Additionally, a single close contact exists between atom Cl15 of the Au4 anion and Au2 (Table 1), which is slightly longer than the shortest reported Au—Cl···Au contact of 3.281 Å found in the CSD (refcode VIMFUS; Dvorkin et al., 1990). Since this Au4 anion uniquely resides in a cavity surrounded predominantly by O atoms, we speculate that this close contact is influenced by its location.

Intermolecular hydroxy-to-carbonyl hydrogen bonds (Table 2, entries 5 and 6) and the one acid-to-hydroxy hydrogen bond (entry 7) are the only interactions where the H atoms involved in the bonding were reliably found.

Within the structure of (I), a network of water molecules was found. It contains close contacts of various types (see Table 1): acid-to-water (entries 9 and 10), hydroxy-to-water (entries 11 and 12), hydroxy-to-hydroxy (entry 13), water-to-acid (entry 14), water-to-carboxyl (entries 15 and 16) and water-to-hydroxy (entry 17). Although the H atoms involved in these bonds could not be found in difference electron-density maps, the proximity of the donor–acceptor atoms clearly demonstrates that hydrogen bonding exists throughout the structure and forms a network of water molecules which threads its way through the cations and anions.

The cations are all joined into a network by either hydrogen bonds or close contacts, through either their hydroxy or their acid functional groups, to adjacent hydration water molecules. These contacts, plus those between the water molecules, form a two-dimensional layer approximately 3.55 Å thick containing all of the O atoms present in the structure and extending in both the a and b cell directions (Fig. 2). These layers are interleaved with sheets of [AuCl₄]^- anions, recurring every quarter of the cell along c. Four of the five anions lie within the alternating parallel sheets of [AuCl₄]^- anions, but the Au4 anion resides within the stratum of O atoms.

The anhydrous salt, (II), of the same toxicologically important marker for cocaine (Fig. 3) shows that the cation and anion are again in close proximity to each other, as was found in (I) and in the gold(III) tetrachloride salt of L-cocaine. Each of the two unique L-ecgonine cations has its quaternary N-bound H atom intramolecularly hydrogen-bonded to its carboxyl C═O group (Table 3).

The two independent [AuCl₄]^- anions of (II) show a bowing of the square-planar arrangement. The Au1 anion has a mean deviation from the plane of 0.0132 (11) Å, with the Au^III center 0.0082 (4) Å below the best plane. One trans pair of Cl atoms is above the best plane by 0.160 (5) Å and the other below the plane by 0.120 (5) Å. The Au2 anion has a mean deviation from the plane of 0.0174 (13) Å, with the Au^III center 0.0117 (5) Å below the best plane. One trans pair of Cl atoms is above the best plane by 0.212 (6) Å and the other below the plane by 0.152 (6) Å.

There are two close hydrogen-bonded contacts involving Cl atoms, one between the hydroxy atom O3A and atom Cl1, and the other between the acid atom O2 and atom Cl2ⁱ [Table 3; symmetry code: (i) x - 1, y + 1/2, -z + 1/2]. There are also two hydrogen bonds involving the hydroxy O atoms, between atoms O3 and O3Aⁱ, and between atoms O2A and O3ⁱⁱ [symmetry code: (ii) -x + 1, y - 1/2, -z + 1/2]. The latter involves the acid H atom in the rare anti configuration.

The powder diffraction pattern of the microcrystals (formed as described by Wood et al., 2007) does not singularly match either the hydrated structure, (I), or the anhydrous structure, (II), of the ecgonine Au^III chloride complex, but has peaks associated with both of them. There are more peaks that are similar to the pure single-crystal generated powder pattern of the anhydrous material, (II), than that of the hydrate, (I). However, we cannot conclusively say that the microcrystal test material is one or the other, or a combination of the two (possibly because of the humidity or lack thereof in the laboratory preparations), or a completely different form.

S2. Experimental

For (I), an aqueous solution (200 µl) containing L-ecgonine hydrochloride (100 µg) was combined with a 0.24% gold(III) chloride (HAuCl₄.3H₂O) solution in 0.24 M HCl (200 µl) [Please check rephrasing]. Slow evaporation of this mixture to dryness produced very light-yellow parallelepipeds of (I), which were used directly for X-ray analysis. For (II), the same preparation was repeated at a later date and the resulting crystals were used for X-ray analysis. These proved to be anhydrous, most probably because of the lack of humidity in the laboratory where the crystals were allowed to grow.

S3. Refinement

All N– and C-bound H atoms, and two of the four hydroxy H atoms for (I) and both of the hydroxy H atoms for (II), were found in electron-density difference maps. For (I), three of the four carboxylic acid H atoms were found, but the remaining acid H atom was disordered and not found. For (II), both of the acid H atoms were located. The hydroxy and acid H atoms were constrained to idealized positions, with distances fixed at O—H = 0.84 Å and with U_iso(H) = 1.5U_eq(O). The methyl H atoms were placed in ideally staggered positions, with C—H = 0.98 Å and U_iso(H) = 1.5U_eq(C). The methylene and methine H atoms were placed in geometrically idealized positions and constrained to ride on their parent C atoms, with C—H = 0.99 and 1.00 Å, respectively, and with U_iso(H) = 1.2U_eq(C). In (I), because of the small contribution to the total electron density in the cell, no water H atoms were found in difference maps.

Computing details

For both compounds, data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. The asymmetric unit of (I), showing the atom-numbering scheme and including nine symmetry-related atoms to show the hydrogen bonding or close contacts. Displacement ellipsoids are drawn at the 40% probability level. All C-bound H atoms have been omitted for clarity. The four monopositive N-protonated L-ecgonine cations are surrounded by five [AuCl4]^- counterions plus seven water molecules, one of which (not identified) could exist as a hydronium ion, for charge balance. Alternatively, one of the hydroxy groups of the cations has to have two protons. Heavy dashed lines indicate the intramolecular hydrogen bond in each cation and the locations of the known hydrogen bonds in the structure. Thin solid lines show the intermolecular close contacts. [Symmetry codes: (i) -x + 1, y + 1/2, -z + 3/2; (ii) -x + 1, y - 1/2, -z + 3/2; (iii) x + 1, y, z; (iv) -x, y + 1/2, -z + 3/2; (v) x - 1, y, z; (vi) x - 1, y + 1, z.]
	Fig. 2. A partial packing diagram for (I), showing two asymmetric units. For the sake of simplicity, only half of the unit cell along the c direction is shown; the other half of the cell is generated by the screw axis. The N—H···O hydrogen bonding within each of the four organic cations and that between molecules is shown by the dashed lines. Thin solid lines show the intermolecular close contacts. The bands of O atoms (shown as full ellipsoids with shaded octants) are clearly seen, and repeat every quarter of the cell length along c. For clarity, all C-bound H atoms have been omitted. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 3. The asymmetric unit of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. All C-bound H atoms have been omitted for clarity. The two independent organic cations of L-ecgonine and their tetrachloroaurate(III) counterions are shown. Three symmetry-related atoms are included to show the hydrogen bonding or close contacts. Heavy dashed lines indicate the intramolecular hydrogen bond in each cation. Thin solid lines show the hydrogen bonding between molecules to various acceptors. [Symmetry codes: (i) -x + 1, y + 1/2, -z + 1/2; (ii) -x + 1, y - 1/2, -z + 1/2.]

(I) Hydronium tetrakis[(1R,2R,3S,5S,8S)- 3-hydroxy-8-methyl-8-azoniabicyclo[3.2.1]octane-2-carboxylate] pentakis[tetrachloridoaurate(III)] hexahydrate

Crystal data

(C9H16NO3)4(H3O)[AuCl4]5·6H2O	F(000) = 4840
Mr = 2565.86	Dx = 2.345 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9389 reflections
a = 9.2153 (16) Å	θ = 3.0–67.4°
b = 15.299 (3) Å	µ = 25.82 mm^−1
c = 51.544 (8) Å	T = 100 K
V = 7267 (2) Å^3	Parallelepiped, yellow
Z = 4	0.35 × 0.11 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	12355 independent reflections
Radiation source: fine-focus sealed tube	12097 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
ϕ and ω scans	θmax = 68.1°, θmin = 1.7°
Absorption correction: numerical (SADABS; Sheldrick, 2001)	h = −10→11
Tmin = 0.040, Tmax = 0.182	k = −17→18
43458 measured reflections	l = −61→47

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0529P)^2 + 20.0246P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
12355 reflections	Δρmax = 3.15 e Å^−3
761 parameters	Δρmin = −1.94 e Å^−3
0 restraints	Absolute structure: Flack (1983), 5212 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.031 (10)

Special details

Experimental. crystal mounted on cryoloop using Paratone-N

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

	x	y	z	Uiso*/Ueq
Au1	0.74862 (5)	0.93435 (3)	0.715499 (8)	0.02738 (10)
Cl1	0.5420 (3)	0.93399 (18)	0.69119 (6)	0.0428 (6)
Cl2	0.7528 (3)	0.78521 (14)	0.71406 (4)	0.0293 (5)
Cl3	0.7363 (3)	1.08209 (16)	0.71804 (5)	0.0379 (6)
Cl4	0.9628 (3)	0.93526 (17)	0.73783 (5)	0.0375 (5)
O1A	0.1554 (8)	0.8451 (5)	0.66339 (15)	0.0371 (17)
O2A	−0.0728 (9)	0.8215 (5)	0.64890 (16)	0.0420 (19)
O3A	0.0555 (8)	0.6494 (5)	0.63127 (13)	0.0322 (15)
N1A	0.2677 (9)	0.7238 (5)	0.69855 (16)	0.0246 (17)
H1NA	0.2816	0.7672	0.6862	0.030*
C1A	0.1077 (11)	0.7106 (6)	0.70197 (18)	0.027 (2)
H1A	0.0664	0.7570	0.7135	0.032*
C2A	0.0357 (11)	0.7137 (6)	0.67500 (19)	0.028 (2)
H2A	−0.0697	0.7008	0.6775	0.033*
C3A	0.0996 (11)	0.6393 (6)	0.65789 (19)	0.029 (2)
H3A	0.0604	0.5824	0.6644	0.035*
C4A	0.2634 (12)	0.6351 (7)	0.65901 (18)	0.030 (2)
H4A1	0.3049	0.6849	0.6492	0.037*
H4A2	0.2972	0.5804	0.6507	0.037*
C5A	0.3166 (12)	0.6382 (6)	0.6871 (2)	0.030 (2)
H5A	0.4245	0.6319	0.6880	0.036*
C6A	0.2402 (12)	0.5736 (7)	0.7054 (2)	0.033 (2)
H6A1	0.3041	0.5581	0.7201	0.040*
H6A2	0.2133	0.5195	0.6960	0.040*
C7A	0.1011 (12)	0.6228 (7)	0.7152 (2)	0.035 (2)
H7A1	0.0120	0.5908	0.7102	0.042*
H7A2	0.1030	0.6295	0.7343	0.042*
C8A	0.3460 (13)	0.7509 (8)	0.72283 (19)	0.039 (2)
H8A1	0.3037	0.8052	0.7295	0.059*
H8A2	0.4489	0.7601	0.7189	0.059*
H8A3	0.3363	0.7049	0.7359	0.059*
C9A	0.0463 (13)	0.8008 (6)	0.66226 (19)	0.034 (2)
Au2	0.30570 (5)	0.92904 (3)	0.794261 (8)	0.02713 (10)
Cl5	0.2768 (3)	0.78095 (16)	0.79691 (7)	0.0480 (7)
Cl6	0.4922 (3)	0.9113 (2)	0.76612 (6)	0.0509 (8)
Cl7	0.1160 (3)	0.94711 (16)	0.82213 (5)	0.0345 (5)
Cl8	0.3296 (3)	1.07667 (15)	0.79252 (5)	0.0379 (6)
O1B	0.9797 (9)	0.6876 (4)	0.84537 (15)	0.0383 (18)
O2B	1.0975 (9)	0.5593 (5)	0.84181 (16)	0.046 (2)
O3B	0.7546 (9)	0.5194 (4)	0.84790 (14)	0.0384 (17)
H3B1	0.7802	0.4671	0.8461	0.046*
N1B	0.8210 (10)	0.7324 (6)	0.80203 (17)	0.0336 (19)
H1NB	0.8530	0.7438	0.8188	0.040*
C1B	0.8963 (12)	0.6514 (7)	0.79179 (18)	0.034 (2)
H1B	0.9954	0.6659	0.7852	0.041*
C2B	0.9046 (12)	0.5830 (6)	0.8140 (2)	0.032 (2)
H2B	0.9489	0.5287	0.8067	0.038*
C3B	0.7496 (13)	0.5605 (7)	0.8233 (2)	0.038 (3)
H3B	0.7035	0.5198	0.8105	0.046*
C4B	0.6522 (13)	0.6426 (7)	0.8264 (2)	0.039 (3)
H4B1	0.5498	0.6242	0.8285	0.046*
H4B2	0.6811	0.6747	0.8423	0.046*
C5B	0.6655 (13)	0.7032 (7)	0.8029 (2)	0.036 (2)
H5B	0.5993	0.7546	0.8048	0.043*
C6B	0.6434 (12)	0.6602 (7)	0.7772 (2)	0.037 (2)
H6B1	0.6089	0.7029	0.7641	0.044*
H6B2	0.5719	0.6121	0.7785	0.044*
C7B	0.7974 (14)	0.6241 (7)	0.7698 (2)	0.039 (3)
H7B1	0.7952	0.5597	0.7681	0.046*
H7B2	0.8308	0.6496	0.7532	0.046*
C8B	0.8517 (14)	0.8102 (7)	0.7852 (2)	0.042 (3)
H8B1	0.9533	0.8276	0.7873	0.063*
H8B2	0.7884	0.8587	0.7904	0.063*
H8B3	0.8333	0.7951	0.7671	0.063*
C9B	0.9985 (14)	0.6135 (7)	0.8352 (2)	0.038 (2)
Au3	0.94049 (4)	0.25918 (2)	0.956030 (8)	0.02640 (9)
Cl9	1.1271 (3)	0.25901 (18)	0.92737 (6)	0.0430 (6)
Cl10	0.7501 (3)	0.26223 (16)	0.98452 (5)	0.0352 (5)
Cl11	0.9699 (3)	0.11302 (15)	0.96206 (5)	0.0345 (5)
Cl12	0.9157 (3)	0.40534 (14)	0.94945 (5)	0.0354 (5)
O1C	0.4233 (9)	0.3312 (5)	0.90561 (15)	0.0399 (18)
O2C	0.5840 (10)	0.3634 (5)	0.87540 (17)	0.049 (2)
O3C	0.5037 (9)	0.5453 (5)	0.87533 (16)	0.0441 (19)
N1C	0.3872 (10)	0.4437 (6)	0.94632 (17)	0.035 (2)
H1NC	0.3450	0.4089	0.9336	0.043*
C1C	0.5536 (13)	0.4461 (8)	0.9423 (2)	0.042 (3)
H1C	0.6022	0.3931	0.9496	0.050*
C2C	0.5787 (14)	0.4553 (7)	0.9126 (2)	0.038 (3)
H2C	0.6856	0.4596	0.9095	0.046*
C3C	0.5077 (13)	0.5403 (7)	0.9030 (2)	0.037 (2)
H3C	0.5678	0.5903	0.9094	0.044*
C4C	0.3571 (14)	0.5521 (7)	0.9133 (2)	0.041 (3)
H4C1	0.3234	0.6118	0.9090	0.049*
H4C2	0.2918	0.5102	0.9044	0.049*
C5C	0.3442 (14)	0.5391 (7)	0.9419 (2)	0.037 (3)
H5C	0.2435	0.5512	0.9482	0.044*
C6C	0.4548 (15)	0.5875 (8)	0.9574 (2)	0.049 (3)
H6C1	0.4201	0.5969	0.9753	0.059*
H6C2	0.4753	0.6451	0.9494	0.059*
C7C	0.5940 (18)	0.5290 (9)	0.9573 (3)	0.061 (4)
H7C1	0.6752	0.5597	0.9486	0.073*
H7C2	0.6235	0.5144	0.9752	0.073*
C8C	0.3478 (16)	0.4101 (9)	0.9723 (2)	0.050 (3)
H8C1	0.4046	0.3574	0.9760	0.075*
H8C2	0.2442	0.3957	0.9726	0.075*
H8C3	0.3685	0.4548	0.9854	0.075*
C9C	0.5216 (13)	0.3768 (6)	0.8975 (2)	0.035 (2)
Au4	0.63437 (4)	0.84234 (3)	0.877377 (7)	0.02490 (9)
Cl13	0.4588 (3)	0.79712 (17)	0.90533 (5)	0.0360 (5)
Cl14	0.7996 (3)	0.77375 (18)	0.90306 (6)	0.0435 (6)
Cl15	0.4669 (3)	0.9127 (2)	0.85256 (6)	0.0476 (7)
Cl16	0.8114 (3)	0.88644 (16)	0.84947 (5)	0.0324 (5)
O1D	0.7144 (8)	0.0187 (4)	0.90788 (13)	0.0307 (15)
O2D	0.7544 (8)	0.1642 (4)	0.90693 (13)	0.0309 (15)
H2D1	0.8146	0.1596	0.8948	0.037*
O3D	0.4181 (8)	0.1525 (4)	0.90101 (13)	0.0322 (15)
H3D1	0.4201	0.2073	0.9023	0.035*
N1D	0.5444 (9)	−0.0414 (5)	0.94958 (17)	0.0303 (19)
H1ND	0.5800	−0.0499	0.9329	0.036*
C1D	0.5945 (10)	0.0475 (6)	0.95921 (17)	0.0228 (19)
H1D	0.6959	0.0456	0.9661	0.027*
C2D	0.5793 (10)	0.1123 (6)	0.93647 (17)	0.0242 (19)
H2D	0.6015	0.1719	0.9434	0.029*
C3D	0.4233 (11)	0.1142 (6)	0.92633 (18)	0.027 (2)
H3D	0.3629	0.1503	0.9384	0.033*
C4D	0.3543 (12)	0.0244 (6)	0.9238 (2)	0.036 (2)
H4D1	0.3965	−0.0059	0.9086	0.043*
H4D2	0.2489	0.0312	0.9207	0.043*
C5D	0.3780 (11)	−0.0318 (6)	0.94815 (19)	0.027 (2)
H5D	0.3281	−0.0897	0.9469	0.033*
C6D	0.3439 (11)	0.0148 (7)	0.9733 (2)	0.033 (2)
H6D1	0.3182	−0.0281	0.9870	0.039*
H6D2	0.2612	0.0553	0.9710	0.039*
C7D	0.4810 (11)	0.0656 (7)	0.98107 (19)	0.031 (2)
H7D1	0.5180	0.0451	0.9980	0.037*
H7D2	0.4600	0.1289	0.9823	0.037*
C8D	0.5951 (12)	−0.1156 (7)	0.9664 (2)	0.035 (2)
H8D1	0.7008	−0.1211	0.9651	0.053*
H8D2	0.5493	−0.1701	0.9606	0.053*
H8D3	0.5681	−0.1041	0.9845	0.053*
C9D	0.6869 (11)	0.0931 (6)	0.91624 (18)	0.027 (2)
Au5	0.98656 (4)	0.75277 (2)	0.966586 (7)	0.02257 (9)
Cl17	0.9949 (3)	0.90185 (14)	0.96923 (5)	0.0340 (5)
Cl18	0.8147 (3)	0.74489 (16)	0.99822 (5)	0.0328 (5)
Cl19	1.1606 (3)	0.75605 (16)	0.93526 (4)	0.0318 (5)
Cl20	0.9784 (3)	0.60447 (14)	0.96329 (5)	0.0312 (5)
O4	0.2397 (9)	0.1265 (5)	0.86078 (15)	0.0400 (18)
O5	0.4390 (9)	0.2617 (5)	0.84436 (15)	0.0412 (18)
O6	0.3090 (10)	0.6638 (7)	0.85737 (18)	0.057 (2)
O7	0.1339 (8)	0.8204 (5)	0.87393 (15)	0.0373 (17)
O8	0.0181 (9)	0.9550 (5)	0.90505 (16)	0.0404 (18)
O9	−0.0546 (12)	0.9287 (6)	0.61145 (17)	0.058 (2)
O10	0.1013 (13)	1.0722 (7)	0.5986 (2)	0.075 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.0269 (2)	0.02786 (18)	0.02739 (18)	0.00195 (16)	0.00045 (17)	−0.00023 (15)
Cl1	0.0370 (15)	0.0415 (12)	0.0501 (14)	0.0089 (12)	−0.0135 (13)	−0.0073 (12)
Cl2	0.0302 (12)	0.0264 (10)	0.0312 (10)	0.0020 (8)	0.0017 (11)	−0.0023 (8)
Cl3	0.0409 (15)	0.0310 (11)	0.0419 (13)	0.0035 (10)	0.0000 (12)	−0.0023 (10)
Cl4	0.0350 (15)	0.0379 (11)	0.0396 (12)	−0.0070 (11)	−0.0079 (11)	0.0079 (11)
O1A	0.035 (5)	0.033 (3)	0.043 (4)	−0.007 (3)	−0.003 (4)	0.000 (3)
O2A	0.038 (5)	0.036 (4)	0.052 (5)	0.007 (3)	−0.002 (4)	0.003 (3)
O3A	0.019 (4)	0.056 (4)	0.022 (3)	−0.001 (3)	0.003 (3)	−0.006 (3)
N1A	0.016 (4)	0.031 (4)	0.026 (4)	−0.005 (3)	−0.002 (3)	−0.003 (3)
C1A	0.026 (6)	0.033 (4)	0.021 (4)	−0.005 (4)	−0.002 (4)	−0.001 (4)
C2A	0.019 (5)	0.036 (5)	0.027 (5)	0.001 (4)	−0.003 (4)	−0.003 (4)
C3A	0.026 (6)	0.034 (5)	0.027 (5)	0.005 (4)	0.004 (4)	−0.003 (4)
C4A	0.031 (6)	0.041 (5)	0.020 (4)	−0.003 (4)	0.004 (4)	0.005 (4)
C5A	0.023 (5)	0.031 (5)	0.037 (5)	0.000 (4)	−0.004 (5)	0.001 (4)
C6A	0.036 (6)	0.037 (5)	0.028 (5)	0.002 (5)	−0.004 (5)	0.012 (4)
C7A	0.028 (6)	0.042 (5)	0.034 (5)	−0.003 (4)	−0.002 (5)	0.003 (4)
C8A	0.036 (6)	0.052 (6)	0.029 (5)	−0.013 (5)	−0.001 (5)	−0.006 (5)
C9A	0.049 (7)	0.032 (5)	0.022 (4)	0.010 (5)	−0.003 (5)	0.000 (4)
Au2	0.0236 (2)	0.02822 (18)	0.02958 (18)	−0.00388 (15)	0.00276 (17)	−0.00384 (15)
Cl5	0.0339 (16)	0.0272 (11)	0.083 (2)	−0.0020 (10)	0.0071 (16)	−0.0114 (12)
Cl6	0.0366 (16)	0.0685 (18)	0.0478 (15)	−0.0171 (14)	0.0170 (14)	−0.0243 (14)
Cl7	0.0276 (13)	0.0403 (12)	0.0355 (11)	0.0082 (10)	0.0062 (11)	0.0021 (10)
Cl8	0.0351 (15)	0.0291 (11)	0.0495 (14)	−0.0051 (10)	−0.0124 (12)	0.0086 (10)
O1B	0.045 (5)	0.033 (4)	0.037 (4)	−0.001 (3)	−0.009 (4)	0.000 (3)
O2B	0.044 (5)	0.054 (5)	0.042 (4)	0.011 (4)	−0.005 (4)	−0.004 (4)
O3B	0.051 (5)	0.029 (3)	0.035 (4)	0.001 (3)	0.006 (4)	0.002 (3)
N1B	0.030 (5)	0.040 (5)	0.031 (4)	−0.002 (4)	−0.002 (4)	0.007 (4)
C1B	0.029 (6)	0.051 (6)	0.022 (4)	−0.004 (5)	0.014 (4)	0.000 (4)
C2B	0.028 (6)	0.036 (5)	0.032 (5)	−0.003 (4)	0.003 (5)	−0.003 (4)
C3B	0.049 (7)	0.030 (5)	0.036 (5)	−0.011 (5)	0.010 (5)	−0.008 (4)
C4B	0.032 (6)	0.043 (6)	0.041 (6)	0.000 (5)	−0.005 (5)	0.002 (5)
C5B	0.032 (6)	0.038 (5)	0.038 (6)	−0.004 (4)	0.013 (5)	0.002 (4)
C6B	0.020 (5)	0.036 (5)	0.054 (6)	0.001 (4)	0.003 (5)	0.001 (5)
C7B	0.049 (7)	0.038 (5)	0.029 (5)	−0.003 (5)	0.005 (5)	0.000 (4)
C8B	0.046 (7)	0.037 (5)	0.042 (6)	−0.007 (5)	−0.003 (6)	0.007 (5)
C9B	0.042 (7)	0.039 (5)	0.034 (5)	−0.006 (5)	0.007 (5)	0.001 (4)
Au3	0.0233 (2)	0.02463 (17)	0.03130 (18)	0.00021 (15)	−0.00206 (17)	0.00141 (15)
Cl9	0.0322 (14)	0.0440 (13)	0.0529 (15)	0.0072 (12)	0.0148 (13)	0.0114 (12)
Cl10	0.0346 (13)	0.0380 (12)	0.0329 (11)	−0.0004 (11)	0.0031 (11)	−0.0028 (10)
Cl11	0.0305 (14)	0.0279 (10)	0.0452 (13)	0.0052 (9)	−0.0019 (11)	0.0059 (10)
Cl12	0.0414 (15)	0.0242 (10)	0.0406 (12)	0.0022 (9)	−0.0001 (12)	0.0022 (9)
O1C	0.044 (5)	0.032 (3)	0.044 (4)	−0.008 (3)	0.019 (4)	−0.002 (3)
O2C	0.060 (6)	0.038 (4)	0.050 (5)	0.000 (4)	0.027 (5)	−0.002 (4)
O3C	0.044 (5)	0.044 (4)	0.044 (4)	0.014 (4)	0.008 (4)	0.007 (4)
N1C	0.030 (5)	0.044 (5)	0.033 (4)	0.012 (4)	0.007 (4)	0.004 (4)
C1C	0.025 (6)	0.050 (6)	0.051 (7)	0.005 (5)	−0.014 (6)	0.000 (5)
C2C	0.037 (7)	0.035 (5)	0.043 (6)	0.001 (4)	0.009 (5)	−0.005 (4)
C3C	0.035 (6)	0.037 (5)	0.038 (6)	0.009 (4)	−0.001 (5)	−0.006 (4)
C4C	0.044 (7)	0.038 (5)	0.041 (6)	0.011 (5)	0.008 (6)	−0.005 (5)
C5C	0.042 (7)	0.040 (5)	0.029 (5)	0.008 (5)	0.011 (5)	0.003 (4)
C6C	0.055 (8)	0.059 (7)	0.034 (5)	0.000 (6)	0.005 (6)	−0.014 (5)
C7C	0.067 (10)	0.067 (8)	0.048 (7)	0.001 (7)	0.006 (7)	−0.016 (7)
C8C	0.053 (8)	0.064 (8)	0.034 (6)	0.000 (6)	0.009 (6)	0.004 (5)
C9C	0.044 (7)	0.032 (5)	0.029 (5)	0.001 (5)	0.005 (5)	0.011 (4)
Au4	0.0206 (2)	0.02911 (17)	0.02497 (17)	−0.00038 (15)	0.00067 (16)	−0.00093 (14)
Cl13	0.0272 (14)	0.0452 (13)	0.0356 (12)	−0.0038 (10)	0.0057 (11)	0.0046 (10)
Cl14	0.0282 (14)	0.0545 (15)	0.0478 (14)	0.0042 (11)	−0.0037 (12)	0.0211 (12)
Cl15	0.0293 (15)	0.0736 (19)	0.0398 (13)	0.0037 (13)	−0.0048 (12)	0.0156 (13)
Cl16	0.0260 (12)	0.0385 (11)	0.0327 (11)	0.0013 (10)	0.0050 (10)	0.0054 (9)
O1D	0.026 (4)	0.035 (4)	0.030 (3)	−0.002 (3)	0.005 (3)	−0.001 (3)
O2D	0.029 (4)	0.032 (3)	0.031 (3)	−0.007 (3)	0.002 (3)	0.002 (3)
O3D	0.033 (4)	0.029 (3)	0.034 (4)	−0.001 (3)	−0.002 (3)	0.002 (3)
N1D	0.021 (5)	0.037 (4)	0.034 (4)	0.003 (3)	0.005 (4)	0.007 (4)
C1D	0.012 (5)	0.031 (4)	0.025 (4)	−0.004 (3)	−0.002 (4)	0.005 (4)
C2D	0.020 (5)	0.029 (4)	0.023 (4)	−0.003 (4)	−0.004 (4)	0.003 (4)
C3D	0.019 (5)	0.038 (5)	0.025 (4)	0.005 (4)	−0.005 (4)	0.003 (4)
C4D	0.024 (6)	0.030 (5)	0.052 (6)	0.001 (4)	−0.011 (5)	0.005 (5)
C5D	0.014 (5)	0.034 (4)	0.034 (5)	0.001 (4)	−0.008 (4)	−0.001 (4)
C6D	0.018 (5)	0.043 (5)	0.038 (5)	−0.002 (4)	0.006 (4)	0.013 (4)
C7D	0.021 (5)	0.039 (5)	0.033 (5)	−0.006 (4)	0.008 (4)	−0.006 (4)
C8D	0.030 (6)	0.036 (5)	0.039 (5)	0.005 (4)	−0.006 (5)	0.010 (4)
C9D	0.023 (5)	0.033 (5)	0.025 (4)	−0.007 (4)	−0.012 (4)	0.001 (4)
Au5	0.01943 (19)	0.02306 (17)	0.02521 (17)	0.00042 (14)	0.00062 (15)	0.00180 (14)
Cl17	0.0395 (15)	0.0225 (9)	0.0400 (12)	−0.0008 (9)	0.0031 (12)	0.0012 (9)
Cl18	0.0315 (12)	0.0333 (10)	0.0335 (10)	0.0051 (10)	0.0100 (10)	0.0062 (9)
Cl19	0.0266 (13)	0.0368 (11)	0.0318 (10)	0.0013 (10)	0.0077 (10)	0.0037 (10)
Cl20	0.0354 (14)	0.0234 (9)	0.0347 (11)	−0.0003 (9)	0.0030 (11)	−0.0020 (9)
O4	0.032 (4)	0.049 (4)	0.040 (4)	0.007 (3)	−0.008 (4)	−0.007 (3)
O5	0.047 (5)	0.039 (4)	0.038 (4)	0.006 (4)	−0.002 (4)	0.000 (3)
O6	0.037 (5)	0.080 (6)	0.053 (5)	0.011 (5)	−0.008 (4)	−0.002 (5)
O7	0.025 (4)	0.047 (4)	0.041 (4)	0.006 (3)	−0.004 (4)	0.003 (3)
O8	0.032 (4)	0.042 (4)	0.047 (4)	0.001 (3)	−0.004 (4)	−0.001 (3)
O9	0.084 (7)	0.049 (5)	0.042 (4)	0.004 (5)	−0.003 (5)	0.000 (4)
O10	0.083 (8)	0.080 (7)	0.062 (6)	−0.023 (6)	0.001 (6)	0.004 (6)

Geometric parameters (Å, º)

Au1—Cl3	2.267 (2)	Au3—Cl10	2.289 (3)
Au1—Cl1	2.279 (3)	O1C—C9C	1.218 (13)
Au1—Cl2	2.283 (2)	O2C—C9C	1.295 (13)
Au1—Cl4	2.285 (3)	O3C—C3C	1.427 (13)
O1A—C9A	1.215 (14)	N1C—C8C	1.479 (13)
O2A—C9A	1.334 (14)	N1C—C5C	1.529 (13)
O3A—C3A	1.439 (11)	N1C—C1C	1.548 (15)
N1A—C1A	1.498 (13)	N1C—H1NC	0.9300
N1A—C8A	1.503 (12)	C1C—C7C	1.529 (17)
N1A—C5A	1.507 (12)	C1C—C2C	1.555 (15)
N1A—H1NA	0.9300	C1C—H1C	1.0000
C1A—C7A	1.508 (13)	C2C—C9C	1.523 (15)
C1A—C2A	1.541 (13)	C2C—C3C	1.539 (15)
C1A—H1A	1.0000	C2C—H2C	1.0000
C2A—C9A	1.489 (13)	C3C—C4C	1.498 (16)
C2A—C3A	1.554 (12)	C3C—H3C	1.0000
C2A—H2A	1.0000	C4C—C5C	1.494 (14)
C3A—C4A	1.513 (15)	C4C—H4C1	0.9900
C3A—H3A	1.0000	C4C—H4C2	0.9900
C4A—C5A	1.527 (13)	C5C—C6C	1.491 (17)
C4A—H4A1	0.9900	C5C—H5C	1.0000
C4A—H4A2	0.9900	C6C—C7C	1.56 (2)
C5A—C6A	1.537 (13)	C6C—H6C1	0.9900
C5A—H5A	1.0000	C6C—H6C2	0.9900
C6A—C7A	1.570 (15)	C7C—H7C1	0.9900
C6A—H6A1	0.9900	C7C—H7C2	0.9900
C6A—H6A2	0.9900	C8C—H8C1	0.9800
C7A—H7A1	0.9900	C8C—H8C2	0.9800
C7A—H7A2	0.9900	C8C—H8C3	0.9800
C8A—H8A1	0.9800	Au4—Cl13	2.274 (3)
C8A—H8A2	0.9800	Au4—Cl14	2.274 (3)
C8A—H8A3	0.9800	Au4—Cl15	2.276 (3)
Au2—Cl6	2.265 (3)	Au4—Cl16	2.277 (3)
Au2—Cl8	2.271 (2)	O1D—C9D	1.243 (12)
Au2—Cl7	2.279 (3)	O2D—C9D	1.342 (11)
Au2—Cl5	2.285 (3)	O2D—H2D1	0.8387
O1B—C9B	1.261 (13)	O3D—C3D	1.431 (11)
O2B—C9B	1.280 (15)	O3D—H3D1	0.8400
O3B—C3B	1.417 (12)	N1D—C8D	1.504 (12)
O3B—H3B1	0.8400	N1D—C1D	1.519 (12)
N1B—C8B	1.498 (12)	N1D—C5D	1.542 (13)
N1B—C5B	1.502 (14)	N1D—H1ND	0.9301
N1B—C1B	1.515 (13)	C1D—C2D	1.541 (12)
N1B—H1NB	0.9301	C1D—C7D	1.562 (13)
C1B—C7B	1.514 (15)	C1D—H1D	1.0000
C1B—C2B	1.552 (13)	C2D—C9D	1.468 (14)
C1B—H1B	1.0000	C2D—C3D	1.530 (13)
C2B—C9B	1.468 (15)	C2D—H2D	1.0000
C2B—C3B	1.546 (16)	C3D—C4D	1.520 (14)
C2B—H2B	1.0010	C3D—H3D	1.0000
C3B—C4B	1.552 (15)	C4D—C5D	1.538 (13)
C3B—H3B	1.0000	C4D—H4D1	0.9900
C4B—C5B	1.533 (14)	C4D—H4D2	0.9900
C4B—H4B1	0.9900	C5D—C6D	1.514 (14)
C4B—H4B2	0.9900	C5D—H5D	1.0000
C5B—C6B	1.491 (15)	C6D—C7D	1.537 (14)
C5B—H5B	1.0000	C6D—H6D1	0.9900
C6B—C7B	1.570 (16)	C6D—H6D2	0.9900
C6B—H6B1	0.9900	C7D—H7D1	0.9900
C6B—H6B2	0.9900	C7D—H7D2	0.9900
C7B—H7B1	0.9900	C8D—H8D1	0.9800
C7B—H7B2	0.9900	C8D—H8D2	0.9800
C8B—H8B1	0.9800	C8D—H8D3	0.9800
C8B—H8B2	0.9800	Au5—Cl19	2.276 (2)
C8B—H8B3	0.9800	Au5—Cl18	2.276 (2)
Au3—Cl9	2.267 (3)	Au5—Cl20	2.276 (2)
Au3—Cl12	2.273 (2)	Au5—Cl17	2.286 (2)
Au3—Cl11	2.274 (2)
O10···Cl14^i	3.217 (11)	O2C···O5	2.600 (12)
O5···Cl1^ii	3.214 (8)	O3A···O4^iv	2.773 (11)
Cl9···O1C^iii	3.150 (8)	O3D···O4	2.676 (11)
Cl15···Au2	3.361 (3)	O3C···O3B	2.739 (11)
O4···O5	2.893 (12)	O6···O2B^v	2.646 (14)
O6···O7	3.012 (12)	O8···O1D^vi	2.967 (11)
O7···O8	2.820 (11)	O7···O1B^v	2.883 (11)
O9···O10	2.707 (15)	O6···O3C	2.713 (12)
O2A···O9	2.538 (12)
Cl3—Au1—Cl1	89.55 (10)	Cl12—Au3—Cl10	89.92 (9)
Cl3—Au1—Cl2	177.60 (10)	Cl11—Au3—Cl10	91.37 (9)
Cl1—Au1—Cl2	89.65 (10)	C8C—N1C—C5C	113.7 (9)
Cl3—Au1—Cl4	90.47 (10)	C8C—N1C—C1C	111.8 (10)
Cl1—Au1—Cl4	176.90 (10)	C5C—N1C—C1C	102.3 (9)
Cl2—Au1—Cl4	90.45 (9)	C8C—N1C—H1NC	109.7
C1A—N1A—C8A	114.3 (8)	C5C—N1C—H1NC	109.5
C1A—N1A—C5A	102.9 (7)	C1C—N1C—H1NC	109.5
C8A—N1A—C5A	115.0 (8)	C7C—C1C—N1C	101.2 (10)
C1A—N1A—H1NA	108.2	C7C—C1C—C2C	112.6 (11)
C8A—N1A—H1NA	108.0	N1C—C1C—C2C	106.3 (9)
C5A—N1A—H1NA	108.0	C7C—C1C—H1C	112.0
N1A—C1A—C7A	102.3 (8)	N1C—C1C—H1C	112.0
N1A—C1A—C2A	108.3 (8)	C2C—C1C—H1C	112.0
C7A—C1A—C2A	114.7 (8)	C9C—C2C—C3C	110.8 (10)
N1A—C1A—H1A	110.4	C9C—C2C—C1C	112.3 (9)
C7A—C1A—H1A	110.4	C3C—C2C—C1C	109.3 (9)
C2A—C1A—H1A	110.4	C9C—C2C—H2C	108.1
C9A—C2A—C1A	113.4 (8)	C3C—C2C—H2C	108.1
C9A—C2A—C3A	112.3 (8)	C1C—C2C—H2C	108.1
C1A—C2A—C3A	109.1 (8)	O3C—C3C—C4C	108.9 (10)
C9A—C2A—H2A	107.2	O3C—C3C—C2C	112.3 (8)
C1A—C2A—H2A	107.2	C4C—C3C—C2C	112.4 (10)
C3A—C2A—H2A	107.2	O3C—C3C—H3C	107.7
O3A—C3A—C4A	108.8 (8)	C4C—C3C—H3C	107.7
O3A—C3A—C2A	110.8 (8)	C2C—C3C—H3C	107.7
C4A—C3A—C2A	112.8 (9)	C5C—C4C—C3C	114.1 (10)
O3A—C3A—H3A	108.1	C5C—C4C—H4C1	108.7
C4A—C3A—H3A	108.1	C3C—C4C—H4C1	108.7
C2A—C3A—H3A	108.1	C5C—C4C—H4C2	108.7
C3A—C4A—C5A	110.8 (9)	C3C—C4C—H4C2	108.7
C3A—C4A—H4A1	109.5	H4C1—C4C—H4C2	107.6
C5A—C4A—H4A1	109.5	C6C—C5C—C4C	114.0 (11)
C3A—C4A—H4A2	109.5	C6C—C5C—N1C	102.6 (10)
C5A—C4A—H4A2	109.5	C4C—C5C—N1C	104.6 (8)
H4A1—C4A—H4A2	108.1	C6C—C5C—H5C	111.7
N1A—C5A—C4A	107.6 (8)	C4C—C5C—H5C	111.7
N1A—C5A—C6A	100.4 (8)	N1C—C5C—H5C	111.7
C4A—C5A—C6A	114.5 (8)	C5C—C6C—C7C	105.9 (10)
N1A—C5A—H5A	111.3	C5C—C6C—H6C1	110.6
C4A—C5A—H5A	111.3	C7C—C6C—H6C1	110.6
C6A—C5A—H5A	111.3	C5C—C6C—H6C2	110.6
C5A—C6A—C7A	105.3 (8)	C7C—C6C—H6C2	110.6
C5A—C6A—H6A1	110.7	H6C1—C6C—H6C2	108.7
C7A—C6A—H6A1	110.7	C1C—C7C—C6C	106.1 (12)
C5A—C6A—H6A2	110.7	C1C—C7C—H7C1	110.5
C7A—C6A—H6A2	110.7	C6C—C7C—H7C1	110.5
H6A1—C6A—H6A2	108.8	C1C—C7C—H7C2	110.5
C1A—C7A—C6A	104.4 (8)	C6C—C7C—H7C2	110.5
C1A—C7A—H7A1	110.9	H7C1—C7C—H7C2	108.7
C6A—C7A—H7A1	110.9	N1C—C8C—H8C1	109.5
C1A—C7A—H7A2	110.9	N1C—C8C—H8C2	109.5
C6A—C7A—H7A2	110.9	H8C1—C8C—H8C2	109.5
H7A1—C7A—H7A2	108.9	N1C—C8C—H8C3	109.5
N1A—C8A—H8A1	109.5	H8C1—C8C—H8C3	109.5
N1A—C8A—H8A2	109.5	H8C2—C8C—H8C3	109.5
H8A1—C8A—H8A2	109.5	O1C—C9C—O2C	122.7 (11)
N1A—C8A—H8A3	109.5	O1C—C9C—C2C	122.4 (10)
H8A1—C8A—H8A3	109.5	O2C—C9C—C2C	114.9 (10)
H8A2—C8A—H8A3	109.5	Cl13—Au4—Cl14	88.12 (10)
O1A—C9A—O2A	124.9 (9)	Cl13—Au4—Cl15	91.01 (10)
O1A—C9A—C2A	122.2 (10)	Cl14—Au4—Cl15	178.58 (12)
O2A—C9A—C2A	112.8 (10)	Cl13—Au4—Cl16	179.46 (10)
Cl6—Au2—Cl8	91.17 (11)	Cl14—Au4—Cl16	91.41 (10)
Cl6—Au2—Cl7	179.25 (11)	Cl15—Au4—Cl16	89.46 (10)
Cl8—Au2—Cl7	88.78 (10)	C9D—O2D—H2D1	120.4
Cl6—Au2—Cl5	90.44 (11)	C3D—O3D—H3D1	109.5
Cl8—Au2—Cl5	178.38 (12)	C8D—N1D—C1D	113.1 (8)
Cl7—Au2—Cl5	89.61 (10)	C8D—N1D—C5D	114.1 (8)
C3B—O3B—H3B1	109.5	C1D—N1D—C5D	103.5 (7)
C8B—N1B—C5B	115.6 (9)	C8D—N1D—H1ND	108.6
C8B—N1B—C1B	111.3 (8)	C1D—N1D—H1ND	108.7
C5B—N1B—C1B	101.7 (8)	C5D—N1D—H1ND	108.6
C8B—N1B—H1NB	109.2	N1D—C1D—C2D	107.4 (7)
C5B—N1B—H1NB	109.4	N1D—C1D—C7D	101.0 (7)
C1B—N1B—H1NB	109.4	C2D—C1D—C7D	111.9 (8)
C7B—C1B—N1B	102.2 (9)	N1D—C1D—H1D	112.0
C7B—C1B—C2B	113.4 (9)	C2D—C1D—H1D	112.0
N1B—C1B—C2B	108.5 (7)	C7D—C1D—H1D	112.0
C7B—C1B—H1B	110.8	C9D—C2D—C3D	113.3 (8)
N1B—C1B—H1B	110.8	C9D—C2D—C1D	110.5 (8)
C2B—C1B—H1B	110.8	C3D—C2D—C1D	111.0 (8)
C9B—C2B—C3B	112.7 (9)	C9D—C2D—H2D	107.3
C9B—C2B—C1B	111.3 (9)	C3D—C2D—H2D	107.3
C3B—C2B—C1B	109.5 (9)	C1D—C2D—H2D	107.3
C9B—C2B—H2B	107.7	O3D—C3D—C4D	106.1 (8)
C3B—C2B—H2B	107.9	O3D—C3D—C2D	110.6 (8)
C1B—C2B—H2B	107.5	C4D—C3D—C2D	113.9 (8)
O3B—C3B—C2B	110.2 (10)	O3D—C3D—H3D	108.7
O3B—C3B—C4B	106.5 (8)	C4D—C3D—H3D	108.7
C2B—C3B—C4B	112.7 (9)	C2D—C3D—H3D	108.7
O3B—C3B—H3B	109.1	C3D—C4D—C5D	112.0 (9)
C2B—C3B—H3B	109.1	C3D—C4D—H4D1	109.2
C4B—C3B—H3B	109.1	C5D—C4D—H4D1	109.2
C5B—C4B—C3B	111.1 (9)	C3D—C4D—H4D2	109.2
C5B—C4B—H4B1	109.4	C5D—C4D—H4D2	109.2
C3B—C4B—H4B1	109.4	H4D1—C4D—H4D2	107.9
C5B—C4B—H4B2	109.4	C6D—C5D—C4D	114.1 (8)
C3B—C4B—H4B2	109.4	C6D—C5D—N1D	102.1 (8)
H4B1—C4B—H4B2	108.0	C4D—C5D—N1D	103.5 (8)
C6B—C5B—N1B	103.7 (9)	C6D—C5D—H5D	112.1
C6B—C5B—C4B	115.2 (9)	C4D—C5D—H5D	112.1
N1B—C5B—C4B	106.2 (9)	N1D—C5D—H5D	112.1
C6B—C5B—H5B	110.5	C5D—C6D—C7D	106.8 (8)
N1B—C5B—H5B	110.5	C5D—C6D—H6D1	110.4
C4B—C5B—H5B	110.5	C7D—C6D—H6D1	110.4
C5B—C6B—C7B	104.3 (9)	C5D—C6D—H6D2	110.4
C5B—C6B—H6B1	110.9	C7D—C6D—H6D2	110.4
C7B—C6B—H6B1	110.9	H6D1—C6D—H6D2	108.6
C5B—C6B—H6B2	110.9	C6D—C7D—C1D	105.9 (8)
C7B—C6B—H6B2	110.9	C6D—C7D—H7D1	110.6
H6B1—C6B—H6B2	108.9	C1D—C7D—H7D1	110.6
C1B—C7B—C6B	105.3 (8)	C6D—C7D—H7D2	110.6
C1B—C7B—H7B1	110.7	C1D—C7D—H7D2	110.6
C6B—C7B—H7B1	110.7	H7D1—C7D—H7D2	108.7
C1B—C7B—H7B2	110.7	N1D—C8D—H8D1	109.5
C6B—C7B—H7B2	110.7	N1D—C8D—H8D2	109.5
H7B1—C7B—H7B2	108.8	H8D1—C8D—H8D2	109.5
N1B—C8B—H8B1	109.5	N1D—C8D—H8D3	109.5
N1B—C8B—H8B2	109.5	H8D1—C8D—H8D3	109.5
H8B1—C8B—H8B2	109.5	H8D2—C8D—H8D3	109.5
N1B—C8B—H8B3	109.5	O1D—C9D—O2D	121.6 (9)
H8B1—C8B—H8B3	109.5	O1D—C9D—C2D	124.5 (9)
H8B2—C8B—H8B3	109.5	O2D—C9D—C2D	113.9 (8)
O1B—C9B—O2B	124.7 (11)	Cl19—Au5—Cl18	178.12 (9)
O1B—C9B—C2B	120.9 (11)	Cl19—Au5—Cl20	89.55 (9)
O2B—C9B—C2B	114.4 (10)	Cl18—Au5—Cl20	88.73 (9)
Cl9—Au3—Cl12	88.87 (10)	Cl19—Au5—Cl17	89.81 (9)
Cl9—Au3—Cl11	89.85 (10)	Cl18—Au5—Cl17	91.92 (9)
Cl12—Au3—Cl11	178.71 (10)	Cl20—Au5—Cl17	179.13 (9)
Cl9—Au3—Cl10	178.67 (10)
C8A—N1A—C1A—C7A	−77.0 (10)	C8C—N1C—C1C—C7C	−78.6 (12)
C5A—N1A—C1A—C7A	48.4 (9)	C5C—N1C—C1C—C7C	43.5 (11)
C8A—N1A—C1A—C2A	161.5 (8)	C8C—N1C—C1C—C2C	163.6 (9)
C5A—N1A—C1A—C2A	−73.1 (9)	C5C—N1C—C1C—C2C	−74.3 (10)
N1A—C1A—C2A—C9A	−65.5 (11)	C7C—C1C—C2C—C9C	−173.2 (11)
C7A—C1A—C2A—C9A	−179.0 (9)	N1C—C1C—C2C—C9C	−63.2 (12)
N1A—C1A—C2A—C3A	60.5 (10)	C7C—C1C—C2C—C3C	−49.8 (14)
C7A—C1A—C2A—C3A	−53.0 (11)	N1C—C1C—C2C—C3C	60.2 (12)
C9A—C2A—C3A—O3A	−42.9 (12)	C9C—C2C—C3C—O3C	−45.1 (14)
C1A—C2A—C3A—O3A	−169.5 (8)	C1C—C2C—C3C—O3C	−169.4 (10)
C9A—C2A—C3A—C4A	79.4 (11)	C9C—C2C—C3C—C4C	78.0 (12)
C1A—C2A—C3A—C4A	−47.2 (11)	C1C—C2C—C3C—C4C	−46.3 (13)
O3A—C3A—C4A—C5A	171.5 (7)	O3C—C3C—C4C—C5C	174.0 (9)
C2A—C3A—C4A—C5A	48.1 (11)	C2C—C3C—C4C—C5C	49.0 (13)
C1A—N1A—C5A—C4A	72.7 (9)	C3C—C4C—C5C—C6C	48.7 (13)
C8A—N1A—C5A—C4A	−162.3 (8)	C3C—C4C—C5C—N1C	−62.7 (13)
C1A—N1A—C5A—C6A	−47.3 (9)	C8C—N1C—C5C—C6C	75.0 (12)
C8A—N1A—C5A—C6A	77.6 (10)	C1C—N1C—C5C—C6C	−45.8 (10)
C3A—C4A—C5A—N1A	−61.2 (10)	C8C—N1C—C5C—C4C	−165.6 (11)
C3A—C4A—C5A—C6A	49.4 (12)	C1C—N1C—C5C—C4C	73.6 (11)
N1A—C5A—C6A—C7A	28.3 (10)	C4C—C5C—C6C—C7C	−83.2 (12)
C4A—C5A—C6A—C7A	−86.6 (10)	N1C—C5C—C6C—C7C	29.4 (12)
N1A—C1A—C7A—C6A	−28.8 (9)	N1C—C1C—C7C—C6C	−25.2 (13)
C2A—C1A—C7A—C6A	88.1 (10)	C2C—C1C—C7C—C6C	87.9 (13)
C5A—C6A—C7A—C1A	0.1 (11)	C5C—C6C—C7C—C1C	−2.3 (14)
C1A—C2A—C9A—O1A	40.1 (14)	C3C—C2C—C9C—O1C	−96.5 (13)
C3A—C2A—C9A—O1A	−84.1 (12)	C1C—C2C—C9C—O1C	26.1 (16)
C1A—C2A—C9A—O2A	−142.7 (9)	C3C—C2C—C9C—O2C	82.5 (13)
C3A—C2A—C9A—O2A	93.1 (11)	C1C—C2C—C9C—O2C	−155.0 (10)
C8B—N1B—C1B—C7B	−78.8 (10)	C8D—N1D—C1D—C2D	162.2 (8)
C5B—N1B—C1B—C7B	44.9 (9)	C5D—N1D—C1D—C2D	−73.9 (9)
C8B—N1B—C1B—C2B	161.2 (9)	C8D—N1D—C1D—C7D	−80.5 (9)
C5B—N1B—C1B—C2B	−75.1 (10)	C5D—N1D—C1D—C7D	43.5 (9)
C7B—C1B—C2B—C9B	−178.5 (9)	N1D—C1D—C2D—C9D	−69.7 (9)
N1B—C1B—C2B—C9B	−65.7 (12)	C7D—C1D—C2D—C9D	−179.7 (8)
C7B—C1B—C2B—C3B	−53.2 (11)	N1D—C1D—C2D—C3D	56.8 (10)
N1B—C1B—C2B—C3B	59.5 (11)	C7D—C1D—C2D—C3D	−53.1 (10)
C9B—C2B—C3B—O3B	−38.5 (12)	C9D—C2D—C3D—O3D	−37.6 (11)
C1B—C2B—C3B—O3B	−162.9 (8)	C1D—C2D—C3D—O3D	−162.5 (7)
C9B—C2B—C3B—C4B	80.3 (12)	C9D—C2D—C3D—C4D	81.8 (10)
C1B—C2B—C3B—C4B	−44.1 (12)	C1D—C2D—C3D—C4D	−43.2 (11)
O3B—C3B—C4B—C5B	167.4 (9)	O3D—C3D—C4D—C5D	169.1 (8)
C2B—C3B—C4B—C5B	46.4 (13)	C2D—C3D—C4D—C5D	47.2 (12)
C8B—N1B—C5B—C6B	74.2 (11)	C3D—C4D—C5D—C6D	48.0 (12)
C1B—N1B—C5B—C6B	−46.5 (10)	C3D—C4D—C5D—N1D	−62.1 (11)
C8B—N1B—C5B—C4B	−164.1 (9)	C8D—N1D—C5D—C6D	79.6 (10)
C1B—N1B—C5B—C4B	75.3 (10)	C1D—N1D—C5D—C6D	−43.7 (9)
C3B—C4B—C5B—C6B	51.6 (13)	C8D—N1D—C5D—C4D	−161.6 (8)
C3B—C4B—C5B—N1B	−62.5 (11)	C1D—N1D—C5D—C4D	75.0 (9)
N1B—C5B—C6B—C7B	29.0 (10)	C4D—C5D—C6D—C7D	−85.2 (10)
C4B—C5B—C6B—C7B	−86.5 (11)	N1D—C5D—C6D—C7D	25.7 (10)
N1B—C1B—C7B—C6B	−26.7 (10)	C5D—C6D—C7D—C1D	0.7 (10)
C2B—C1B—C7B—C6B	89.8 (10)	N1D—C1D—C7D—C6D	−27.1 (9)
C5B—C6B—C7B—C1B	−1.2 (11)	C2D—C1D—C7D—C6D	86.9 (9)
C3B—C2B—C9B—O1B	−71.3 (13)	C3D—C2D—C9D—O1D	−79.9 (12)
C1B—C2B—C9B—O1B	52.1 (14)	C1D—C2D—C9D—O1D	45.4 (13)
C3B—C2B—C9B—O2B	108.9 (11)	C3D—C2D—C9D—O2D	99.4 (10)
C1B—C2B—C9B—O2B	−127.7 (10)	C1D—C2D—C9D—O2D	−135.4 (8)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) x+1, y, z; (iv) −x, y+1/2, −z+3/2; (v) x−1, y, z; (vi) x−1, y+1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O1A	0.93	2.04	2.792 (11)	137
N1B—H1NB···O1B	0.93	1.99	2.757 (11)	138
N1C—H1NC···O1C	0.93	2.00	2.734 (12)	134
N1D—H1ND···O1D	0.93	2.07	2.814 (11)	136
O3D—H3D1···O1C	0.84	1.90	2.743 (10)	179
O3B—H3B1···O1A^ii	0.84	2.02	2.852 (10)	172
O2D—H2D1···O3A^ii	0.84	1.81	2.645 (10)	180

Symmetry code: (ii) −x+1, y−1/2, −z+3/2.

(II) (1R,2R,3S,5S,8S)-3-hydroxy-8-methyl-8- azoniabicyclo[3.2.1]octane-2-carboxylate tetrachloridoaurate(III)

Crystal data

(C9H16NO3)[AuCl4]	F(000) = 1984
Mr = 524.99	Dx = 2.371 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9469 reflections
a = 10.0276 (1) Å	θ = 3.7–66.9°
b = 15.7339 (2) Å	µ = 25.50 mm^−1
c = 18.6416 (2) Å	T = 100 K
V = 2941.15 (6) Å^3	Parallelepiped, gold
Z = 8	0.23 × 0.17 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	5121 independent reflections
Radiation source: fine-focus sealed tube	5053 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ϕ and ω scans	θmax = 67.2°, θmin = 3.7°
Absorption correction: numerical (SADABS; Sheldrick, 2001)	h = −11→11
Tmin = 0.067, Tmax = 0.185	k = −18→17
22091 measured reflections	l = −21→21

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.018	w = 1/[σ^2(Fo^2) + (0.0249P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.047	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.93 e Å^−3
5121 reflections	Δρmin = −0.69 e Å^−3
332 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.000106 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 2199 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.004 (7)

Special details

Experimental. crystal mounted on cryoloop using Paratone-N

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

	x	y	z	Uiso*/Ueq
Au1	0.187321 (15)	0.505994 (11)	0.090196 (8)	0.01499 (6)
Cl1	0.34843 (9)	0.50710 (7)	0.00321 (4)	0.01889 (19)
Cl2	0.19401 (10)	0.36001 (6)	0.09469 (6)	0.0236 (2)
Cl3	0.02630 (9)	0.50577 (8)	0.17652 (5)	0.0244 (2)
Cl4	0.18470 (11)	0.65024 (6)	0.08728 (6)	0.0228 (2)
O1	0.4912 (3)	0.75884 (19)	0.33650 (15)	0.0215 (7)
O2	0.4994 (3)	0.8345 (2)	0.43767 (16)	0.0272 (7)
H2	0.5809	0.8370	0.4277	0.041*
O3	0.2823 (3)	0.92123 (18)	0.34524 (16)	0.0223 (7)
H3	0.2952	0.9412	0.3865	0.033*
N1	0.2625 (3)	0.6623 (2)	0.32007 (17)	0.0147 (7)
H1	0.3475	0.6796	0.3064	0.018*
C1	0.2355 (4)	0.6914 (3)	0.3961 (2)	0.0159 (9)
H1B	0.2779	0.6525	0.4318	0.019*
C2	0.2891 (4)	0.7822 (3)	0.4035 (2)	0.0160 (9)
H2B	0.2720	0.8022	0.4536	0.019*
C3	0.2151 (4)	0.8422 (3)	0.3508 (2)	0.0166 (8)
H3B	0.1228	0.8524	0.3692	0.020*
C4	0.2061 (4)	0.8043 (3)	0.2760 (2)	0.0171 (8)
H4A	0.2948	0.8072	0.2528	0.021*
H4B	0.1432	0.8383	0.2468	0.021*
C5	0.1593 (4)	0.7119 (3)	0.2776 (2)	0.0157 (9)
H5A	0.1490	0.6885	0.2280	0.019*
C6	0.0330 (4)	0.6984 (3)	0.3219 (2)	0.0163 (9)
H6A	−0.0156	0.6472	0.3055	0.020*
H6B	−0.0269	0.7482	0.3180	0.020*
C7	0.0820 (4)	0.6870 (3)	0.4003 (2)	0.0169 (8)
H7A	0.0467	0.7328	0.4313	0.020*
H7B	0.0528	0.6315	0.4197	0.020*
C8	0.2514 (4)	0.5682 (3)	0.3122 (3)	0.0234 (10)
H8A	0.3174	0.5404	0.3431	0.035*
H8B	0.2679	0.5524	0.2621	0.035*
H8C	0.1616	0.5499	0.3261	0.035*
C9	0.4370 (4)	0.7886 (3)	0.3887 (2)	0.0173 (9)
Au2	0.792368 (15)	0.510510 (11)	−0.096686 (8)	0.01529 (6)
Cl5	0.58515 (10)	0.53140 (7)	−0.14391 (6)	0.0281 (2)
Cl6	0.76093 (11)	0.36699 (6)	−0.09842 (6)	0.0257 (2)
Cl7	0.99890 (10)	0.49006 (8)	−0.04920 (6)	0.0310 (2)
Cl8	0.82924 (10)	0.65411 (6)	−0.09756 (6)	0.0217 (2)
O1A	0.4689 (3)	0.64723 (18)	0.20930 (15)	0.0193 (6)
O2A	0.5411 (3)	0.51678 (18)	0.22023 (17)	0.0284 (7)
H2A	0.6078	0.4880	0.2079	0.043*
O3A	0.6462 (3)	0.54127 (17)	0.06095 (15)	0.0192 (6)
H3A	0.5632	0.5437	0.0552	0.029*
N1A	0.6350 (4)	0.7758 (2)	0.16987 (18)	0.0169 (8)
H1A	0.5495	0.7540	0.1758	0.020*
C1A	0.7366 (4)	0.7113 (3)	0.1973 (2)	0.0158 (9)
H1C	0.7436	0.7134	0.2508	0.019*
C2A	0.6950 (4)	0.6225 (3)	0.1715 (2)	0.0156 (8)
H2C	0.7631	0.5807	0.1886	0.019*
C3A	0.6934 (4)	0.6208 (2)	0.0877 (2)	0.0147 (8)
H3C	0.7881	0.6267	0.0715	0.018*
C4A	0.6174 (4)	0.6958 (3)	0.0570 (2)	0.0154 (8)
H4A1	0.5211	0.6893	0.0673	0.018*
H4A2	0.6290	0.6973	0.0043	0.018*
C5A	0.6683 (4)	0.7793 (3)	0.0898 (2)	0.0170 (9)
H5B	0.6266	0.8298	0.0662	0.020*
C6A	0.8205 (4)	0.7862 (3)	0.0909 (2)	0.0207 (9)
H6A1	0.8486	0.8465	0.0901	0.025*
H6A2	0.8597	0.7570	0.0488	0.025*
C7A	0.8658 (5)	0.7426 (3)	0.1619 (2)	0.0200 (10)
H7A1	0.9263	0.6944	0.1517	0.024*
H7A2	0.9126	0.7836	0.1933	0.024*
C8A	0.6444 (5)	0.8597 (3)	0.2061 (2)	0.0219 (9)
H8A1	0.6286	0.8525	0.2577	0.033*
H8A2	0.5772	0.8982	0.1861	0.033*
H8A3	0.7335	0.8836	0.1985	0.033*
C9A	0.5599 (4)	0.5970 (3)	0.2022 (2)	0.0180 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.01423 (9)	0.01405 (9)	0.01670 (8)	−0.00097 (6)	−0.00022 (5)	0.00066 (7)
Cl1	0.0183 (4)	0.0180 (5)	0.0204 (4)	0.0005 (4)	0.0034 (3)	0.0013 (4)
Cl2	0.0219 (5)	0.0138 (5)	0.0351 (6)	0.0001 (4)	0.0027 (5)	0.0044 (5)
Cl3	0.0223 (5)	0.0249 (6)	0.0261 (4)	−0.0035 (5)	0.0072 (4)	−0.0020 (5)
Cl4	0.0323 (6)	0.0146 (5)	0.0214 (5)	−0.0012 (4)	0.0051 (5)	−0.0023 (4)
O1	0.0161 (15)	0.0243 (18)	0.0241 (16)	−0.0009 (12)	0.0010 (13)	−0.0065 (13)
O2	0.0215 (16)	0.036 (2)	0.0239 (15)	−0.0103 (14)	−0.0002 (13)	−0.0042 (14)
O3	0.0287 (17)	0.0103 (15)	0.0278 (16)	−0.0041 (13)	0.0007 (14)	0.0014 (12)
N1	0.0142 (17)	0.0122 (17)	0.0176 (16)	−0.0025 (13)	0.0007 (14)	0.0005 (14)
C1	0.020 (2)	0.014 (2)	0.0138 (19)	0.0007 (16)	−0.0026 (17)	0.0016 (17)
C2	0.019 (2)	0.0124 (19)	0.017 (2)	−0.0042 (16)	−0.0017 (18)	0.0007 (17)
C3	0.014 (2)	0.014 (2)	0.022 (2)	−0.0005 (18)	−0.0019 (17)	0.0026 (17)
C4	0.013 (2)	0.021 (2)	0.0173 (19)	0.0002 (18)	−0.0028 (17)	0.0007 (17)
C5	0.017 (2)	0.018 (2)	0.0125 (18)	0.0024 (17)	−0.0019 (17)	0.0006 (16)
C6	0.015 (2)	0.012 (2)	0.022 (2)	−0.0016 (17)	−0.0008 (16)	−0.0019 (17)
C7	0.020 (2)	0.016 (2)	0.0150 (19)	−0.0036 (16)	0.0035 (18)	0.0010 (18)
C8	0.023 (2)	0.012 (2)	0.035 (2)	0.0007 (17)	0.0045 (19)	−0.0042 (19)
C9	0.021 (2)	0.014 (2)	0.017 (2)	−0.0021 (17)	−0.0038 (17)	0.0040 (17)
Au2	0.01305 (9)	0.01716 (9)	0.01567 (8)	−0.00069 (6)	−0.00083 (6)	−0.00075 (7)
Cl5	0.0175 (5)	0.0231 (6)	0.0438 (6)	−0.0053 (4)	−0.0106 (4)	0.0110 (5)
Cl6	0.0267 (5)	0.0168 (5)	0.0337 (5)	−0.0003 (4)	−0.0055 (5)	0.0013 (5)
Cl7	0.0207 (5)	0.0338 (7)	0.0386 (5)	0.0027 (5)	−0.0126 (4)	−0.0025 (6)
Cl8	0.0214 (5)	0.0186 (5)	0.0250 (5)	−0.0039 (4)	0.0006 (5)	−0.0026 (5)
O1A	0.0209 (15)	0.0143 (15)	0.0228 (15)	0.0028 (13)	0.0048 (12)	0.0007 (12)
O2A	0.0314 (17)	0.0112 (15)	0.0426 (17)	0.0021 (13)	0.0172 (14)	0.0081 (15)
O3A	0.0201 (15)	0.0119 (15)	0.0256 (14)	0.0002 (12)	−0.0030 (12)	−0.0022 (12)
N1A	0.021 (2)	0.0099 (18)	0.0193 (18)	−0.0019 (15)	0.0020 (15)	0.0002 (14)
C1A	0.016 (2)	0.015 (2)	0.0163 (19)	−0.0005 (17)	−0.0038 (17)	0.0017 (17)
C2A	0.015 (2)	0.014 (2)	0.0187 (19)	0.0012 (16)	0.0000 (16)	0.0031 (16)
C3A	0.016 (2)	0.0102 (19)	0.0172 (19)	0.0000 (15)	0.0007 (16)	−0.0015 (16)
C4A	0.016 (2)	0.013 (2)	0.0176 (19)	0.0012 (16)	−0.0013 (16)	0.0017 (17)
C5A	0.023 (2)	0.013 (2)	0.015 (2)	0.0005 (16)	0.0019 (18)	0.0040 (17)
C6A	0.021 (2)	0.015 (2)	0.026 (2)	−0.0039 (16)	0.001 (2)	0.0044 (19)
C7A	0.017 (2)	0.013 (2)	0.030 (2)	−0.0030 (17)	−0.0013 (19)	−0.0009 (19)
C8A	0.030 (2)	0.015 (2)	0.021 (2)	−0.0008 (19)	0.0007 (18)	−0.0024 (18)
C9A	0.019 (2)	0.015 (2)	0.0195 (19)	−0.0030 (18)	0.0031 (16)	0.0002 (17)

Geometric parameters (Å, º)

Au1—Cl4	2.2704 (10)	C4—C5	1.528 (6)
Au1—Cl3	2.2796 (9)	C4—H4A	0.9900
Au1—Cl1	2.2890 (8)	C4—H4B	0.9900
Au1—Cl2	2.2994 (10)	C5—C6	1.526 (6)
Au2—Cl7	2.2752 (9)	C5—H5A	1.0000
Au2—Cl6	2.2803 (10)	C6—C7	1.552 (5)
Au2—Cl5	2.2805 (10)	C6—H6A	0.9900
Au2—Cl8	2.2895 (10)	C6—H6B	0.9900
O1—C9	1.209 (5)	C7—H7A	0.9900
O2—C9	1.322 (5)	C7—H7B	0.9900
O2—H2	0.8400	C8—H8A	0.9800
O3—C3	1.419 (5)	C8—H8B	0.9800
O3—H3	0.8400	C8—H8C	0.9800
O1A—C9A	1.214 (5)	C1A—C2A	1.535 (5)
O2A—C9A	1.320 (5)	C1A—C7A	1.535 (6)
O2A—H2A	0.8400	C1A—H1C	1.0000
O3A—C3A	1.428 (4)	C2A—C9A	1.525 (5)
O3A—H3A	0.8400	C2A—C3A	1.563 (5)
N1—C8	1.492 (5)	C2A—H2C	1.0000
N1—C1	1.514 (5)	C3A—C4A	1.518 (5)
N1—C5	1.518 (5)	C3A—H3C	1.0000
N1—H1	0.9300	C4A—C5A	1.536 (5)
N1A—C8A	1.486 (5)	C4A—H4A1	0.9900
N1A—C1A	1.526 (5)	C4A—H4A2	0.9900
N1A—C5A	1.531 (5)	C5A—C6A	1.530 (6)
N1A—H1A	0.9300	C5A—H5B	1.0000
C1—C2	1.532 (6)	C6A—C7A	1.559 (6)
C1—C7	1.543 (6)	C6A—H6A1	0.9900
C1—H1B	1.0000	C6A—H6A2	0.9900
C2—C9	1.512 (6)	C7A—H7A1	0.9900
C2—C3	1.552 (5)	C7A—H7A2	0.9900
C2—H2B	1.0000	C8A—H8A1	0.9800
C3—C4	1.519 (5)	C8A—H8A2	0.9800
C3—H3B	1.0000	C8A—H8A3	0.9800
Cl4—Au1—Cl3	90.59 (4)	C1—C7—H7A	110.7
Cl4—Au1—Cl1	89.06 (4)	C6—C7—H7A	110.7
Cl3—Au1—Cl1	179.60 (4)	C1—C7—H7B	110.7
Cl4—Au1—Cl2	178.76 (4)	C6—C7—H7B	110.7
Cl3—Au1—Cl2	89.62 (4)	H7A—C7—H7B	108.8
Cl1—Au1—Cl2	90.73 (4)	N1—C8—H8A	109.5
Cl7—Au2—Cl6	89.50 (4)	N1—C8—H8B	109.5
Cl7—Au2—Cl5	179.76 (5)	H8A—C8—H8B	109.5
Cl6—Au2—Cl5	90.65 (4)	N1—C8—H8C	109.5
Cl7—Au2—Cl8	89.73 (4)	H8A—C8—H8C	109.5
Cl6—Au2—Cl8	178.18 (4)	H8B—C8—H8C	109.5
Cl5—Au2—Cl8	90.12 (4)	O1—C9—O2	123.7 (4)
C9—O2—H2	109.5	O1—C9—C2	124.2 (4)
C3—O3—H3	109.5	O2—C9—C2	112.0 (4)
C9A—O2A—H2A	109.5	N1A—C1A—C2A	108.6 (3)
C3A—O3A—H3A	109.5	N1A—C1A—C7A	101.9 (3)
C8—N1—C1	112.3 (3)	C2A—C1A—C7A	112.7 (3)
C8—N1—C5	114.0 (3)	N1A—C1A—H1C	111.1
C1—N1—C5	102.2 (3)	C2A—C1A—H1C	111.1
C8—N1—H1	109.4	C7A—C1A—H1C	111.1
C1—N1—H1	109.4	C9A—C2A—C1A	111.3 (3)
C5—N1—H1	109.4	C9A—C2A—C3A	111.2 (3)
C8A—N1A—C1A	113.3 (3)	C1A—C2A—C3A	109.4 (3)
C8A—N1A—C5A	113.4 (3)	C9A—C2A—H2C	108.3
C1A—N1A—C5A	101.8 (3)	C1A—C2A—H2C	108.3
C8A—N1A—H1A	109.3	C3A—C2A—H2C	108.3
C1A—N1A—H1A	109.3	O3A—C3A—C4A	112.5 (3)
C5A—N1A—H1A	109.3	O3A—C3A—C2A	111.6 (3)
N1—C1—C2	107.7 (3)	C4A—C3A—C2A	111.6 (3)
N1—C1—C7	102.3 (3)	O3A—C3A—H3C	106.9
C2—C1—C7	112.8 (3)	C4A—C3A—H3C	106.9
N1—C1—H1B	111.2	C2A—C3A—H3C	106.9
C2—C1—H1B	111.2	C3A—C4A—C5A	110.4 (3)
C7—C1—H1B	111.2	C3A—C4A—H4A1	109.6
C9—C2—C1	112.9 (3)	C5A—C4A—H4A1	109.6
C9—C2—C3	108.3 (3)	C3A—C4A—H4A2	109.6
C1—C2—C3	110.0 (3)	C5A—C4A—H4A2	109.6
C9—C2—H2B	108.5	H4A1—C4A—H4A2	108.1
C1—C2—H2B	108.5	N1A—C5A—C6A	102.0 (3)
C3—C2—H2B	108.5	N1A—C5A—C4A	106.5 (3)
O3—C3—C4	107.8 (3)	C6A—C5A—C4A	113.4 (4)
O3—C3—C2	110.6 (3)	N1A—C5A—H5B	111.5
C4—C3—C2	111.8 (3)	C6A—C5A—H5B	111.5
O3—C3—H3B	108.9	C4A—C5A—H5B	111.5
C4—C3—H3B	108.9	C5A—C6A—C7A	105.7 (3)
C2—C3—H3B	108.9	C5A—C6A—H6A1	110.6
C3—C4—C5	111.9 (3)	C7A—C6A—H6A1	110.6
C3—C4—H4A	109.2	C5A—C6A—H6A2	110.6
C5—C4—H4A	109.2	C7A—C6A—H6A2	110.6
C3—C4—H4B	109.2	H6A1—C6A—H6A2	108.7
C5—C4—H4B	109.2	C1A—C7A—C6A	105.1 (3)
H4A—C4—H4B	107.9	C1A—C7A—H7A1	110.7
N1—C5—C6	102.2 (3)	C6A—C7A—H7A1	110.7
N1—C5—C4	106.8 (3)	C1A—C7A—H7A2	110.7
C6—C5—C4	113.4 (3)	C6A—C7A—H7A2	110.7
N1—C5—H5A	111.3	H7A1—C7A—H7A2	108.8
C6—C5—H5A	111.3	N1A—C8A—H8A1	109.5
C4—C5—H5A	111.3	N1A—C8A—H8A2	109.5
C5—C6—C7	105.2 (3)	H8A1—C8A—H8A2	109.5
C5—C6—H6A	110.7	N1A—C8A—H8A3	109.5
C7—C6—H6A	110.7	H8A1—C8A—H8A3	109.5
C5—C6—H6B	110.7	H8A2—C8A—H8A3	109.5
C7—C6—H6B	110.7	O1A—C9A—O2A	119.2 (4)
H6A—C6—H6B	108.8	O1A—C9A—C2A	122.5 (4)
C1—C7—C6	105.2 (3)	O2A—C9A—C2A	118.3 (4)
C8—N1—C1—C2	163.4 (3)	C8A—N1A—C1A—C2A	165.3 (3)
C5—N1—C1—C2	−74.0 (4)	C5A—N1A—C1A—C2A	−72.6 (4)
C8—N1—C1—C7	−77.6 (4)	C8A—N1A—C1A—C7A	−75.6 (4)
C5—N1—C1—C7	45.0 (4)	C5A—N1A—C1A—C7A	46.6 (4)
N1—C1—C2—C9	−59.5 (4)	N1A—C1A—C2A—C9A	−62.4 (4)
C7—C1—C2—C9	−171.6 (4)	C7A—C1A—C2A—C9A	−174.6 (3)
N1—C1—C2—C3	61.5 (4)	N1A—C1A—C2A—C3A	60.8 (4)
C7—C1—C2—C3	−50.6 (4)	C7A—C1A—C2A—C3A	−51.3 (4)
C9—C2—C3—O3	−43.2 (5)	C9A—C2A—C3A—O3A	−52.5 (4)
C1—C2—C3—O3	−167.0 (3)	C1A—C2A—C3A—O3A	−175.9 (3)
C9—C2—C3—C4	76.9 (4)	C9A—C2A—C3A—C4A	74.4 (4)
C1—C2—C3—C4	−46.9 (4)	C1A—C2A—C3A—C4A	−49.0 (4)
O3—C3—C4—C5	169.2 (3)	O3A—C3A—C4A—C5A	177.7 (3)
C2—C3—C4—C5	47.4 (5)	C2A—C3A—C4A—C5A	51.3 (4)
C8—N1—C5—C6	74.9 (4)	C8A—N1A—C5A—C6A	76.1 (4)
C1—N1—C5—C6	−46.5 (4)	C1A—N1A—C5A—C6A	−45.9 (4)
C8—N1—C5—C4	−165.7 (3)	C8A—N1A—C5A—C4A	−164.7 (3)
C1—N1—C5—C4	72.9 (4)	C1A—N1A—C5A—C4A	73.2 (4)
C3—C4—C5—N1	−61.4 (4)	C3A—C4A—C5A—N1A	−64.6 (4)
C3—C4—C5—C6	50.5 (5)	C3A—C4A—C5A—C6A	46.8 (5)
N1—C5—C6—C7	29.4 (4)	N1A—C5A—C6A—C7A	27.3 (4)
C4—C5—C6—C7	−85.3 (4)	C4A—C5A—C6A—C7A	−86.8 (4)
N1—C1—C7—C6	−26.3 (4)	N1A—C1A—C7A—C6A	−29.1 (4)
C2—C1—C7—C6	89.1 (4)	C2A—C1A—C7A—C6A	87.1 (4)
C5—C6—C7—C1	−2.0 (4)	C5A—C6A—C7A—C1A	1.0 (4)
C1—C2—C9—O1	49.5 (5)	C1A—C2A—C9A—O1A	38.2 (5)
C3—C2—C9—O1	−72.5 (5)	C3A—C2A—C9A—O1A	−84.1 (5)
C1—C2—C9—O2	−134.0 (4)	C1A—C2A—C9A—O2A	−143.3 (4)
C3—C2—C9—O2	104.1 (4)	C3A—C2A—C9A—O2A	94.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.93	1.99	2.768 (4)	140
N1A—H1A···O1A	0.93	1.97	2.721 (5)	137
O3A—H3A···Cl1	0.84	2.43	3.219 (3)	157
O2—H2···Cl2^i	0.84	2.32	3.159 (3)	173
O3—H3···O3A^i	0.84	1.95	2.672 (4)	144
O2A—H2A···O3^ii	0.84	1.82	2.624 (4)	161

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