Understanding the microcrystal tests of three related phenethyl­amines: the ortho-metallated (±)-amphetamine formed with gold(III) chloride, and the tetra­chloridoaurate(III) salts of (+)-methamphetamine and (±)-ephedrine

The ortho-metallation product of the reaction of (±)-amphetamine with gold(III) chloride, [D,L-2-(2-amino­prop­yl)phenyl-κ²N,C¹]dichlorido­gold(III), [Au(C₉H₁₂N)Cl₂], and the two salts resulting from crystallization of (+)-methamphetamine with gold(III) chloride, D-meth­yl(1-phenyl­propan-2-yl)aza­nium tetra­chlorido­aurate(III), (C₁₀H₁₆N)[AuCl₄], and of (±)-ephedrine with gold(III) chloride, D,L-(1-hy­droxy-1-phenyl­propan-2-yl)(methyl)aza­nium tetra­chlorido­aurate(III), (C₁₀H₁₆NO)[AuCl₄], have different structures. The first makes a bidentate complex directly with a dichloridogold(III) group, forming a six-membered ring structure; the second and third each form a salt with [AuCl₄]⁻ (each has two formula units in the asymmetric unit). The organic components are all members of the same class of stimulants that are prevalent in illicit drug use. These structures are important contributions to the understanding of the microcrystal tests for these drugs that have been employed for well over 100 years.

Computing details

For all compounds, data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008b); program(s) used to refine structure: SHELXTL (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

(I) [D,L-2-(2-Aminopropyl)phenyl-κ²N,C¹]dichloridogold(III)

Crystal data

[Au(C9H12N)Cl2]	F(000) = 1488
Mr = 402.06	Dx = 2.396 Mg m^−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9913 reflections
a = 9.1323 (2) Å	θ = 3.3–70.5°
b = 8.9812 (2) Å	µ = 28.84 mm^−1
c = 27.1824 (6) Å	T = 100 K
V = 2229.50 (9) Å^3	Block, yellow
Z = 8	0.42 × 0.30 × 0.24 mm

Data collection

Bruker SMART CCD APEXII area-detector diffractometer	2039 independent reflections
Radiation source: fine-focus sealed tube	2014 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
φ and ω scans	θmax = 71.2°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −10→10
Tmin = 0.029, Tmax = 0.055	k = −10→10
20023 measured reflections	l = −32→31

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)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0377P)^2 + 42.8278P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max < 0.001
2039 reflections	Δρmax = 2.12 e Å^−3
120 parameters	Δρmin = −2.79 e Å^−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00022 (2)

Special details

Experimental. crystal mounted on a Cryoloop using Paratone-N

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 (Ų)

	x	y	z	Uiso*/Ueq
Au1	1.07844 (4)	0.01245 (4)	0.407089 (12)	0.01872 (18)
Cl1	1.1273 (3)	−0.2166 (3)	0.37581 (10)	0.0393 (6)
Cl2	1.2031 (2)	−0.0494 (3)	0.48269 (7)	0.0314 (5)
N1	1.0337 (9)	0.2134 (8)	0.4411 (3)	0.0245 (15)
H1A	1.0066	0.1920	0.4730	0.029*
H1B	1.1207	0.2649	0.4429	0.029*
C1	0.9702 (10)	0.0730 (10)	0.3438 (3)	0.0244 (18)
C2	1.0233 (12)	0.0245 (11)	0.2987 (3)	0.032 (2)
H2	1.1069	−0.0382	0.2966	0.038*
C3	0.9492 (13)	0.0714 (14)	0.2564 (4)	0.046 (3)
H3	0.9831	0.0401	0.2250	0.055*
C4	0.8291 (12)	0.1614 (14)	0.2595 (4)	0.045 (3)
H4	0.7797	0.1916	0.2304	0.054*
C5	0.7785 (11)	0.2094 (12)	0.3057 (3)	0.035 (2)
H5	0.6951	0.2723	0.3076	0.042*
C6	0.8494 (10)	0.1656 (10)	0.3485 (3)	0.0269 (19)
C7	0.7994 (11)	0.2290 (11)	0.3965 (3)	0.033 (2)
H7A	0.7686	0.1471	0.4185	0.040*
H7B	0.7138	0.2944	0.3909	0.040*
C8	0.9221 (11)	0.3185 (11)	0.4211 (3)	0.033 (2)
H8	0.8784	0.3738	0.4494	0.040*
C9	0.9934 (14)	0.4297 (11)	0.3881 (4)	0.046 (3)
H9A	1.0425	0.3778	0.3610	0.069*
H9B	1.0655	0.4871	0.4069	0.069*
H9C	0.9189	0.4971	0.3748	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.0216 (3)	0.0200 (2)	0.0146 (2)	−0.00106 (12)	0.00058 (12)	0.00607 (12)
Cl1	0.0445 (14)	0.0272 (11)	0.0462 (14)	0.0075 (10)	−0.0041 (11)	−0.0072 (10)
Cl2	0.0375 (12)	0.0409 (12)	0.0159 (10)	0.0136 (10)	0.0023 (8)	0.0125 (9)
N1	0.038 (4)	0.024 (4)	0.012 (3)	0.004 (3)	−0.004 (3)	0.000 (3)
C1	0.026 (4)	0.030 (5)	0.017 (4)	−0.008 (4)	0.000 (3)	0.007 (3)
C2	0.038 (5)	0.043 (6)	0.015 (4)	−0.018 (4)	0.005 (4)	−0.004 (4)
C3	0.054 (7)	0.066 (7)	0.017 (5)	−0.029 (6)	0.009 (4)	−0.005 (5)
C4	0.040 (6)	0.072 (8)	0.023 (5)	−0.017 (6)	−0.013 (4)	0.016 (5)
C5	0.030 (5)	0.049 (6)	0.027 (5)	−0.005 (4)	−0.007 (4)	0.014 (4)
C6	0.024 (4)	0.032 (5)	0.025 (4)	−0.008 (4)	−0.006 (3)	0.009 (4)
C7	0.036 (5)	0.037 (5)	0.026 (5)	0.008 (4)	−0.003 (4)	0.008 (4)
C8	0.050 (6)	0.029 (5)	0.020 (5)	0.011 (4)	−0.005 (4)	−0.002 (4)
C9	0.068 (8)	0.022 (5)	0.048 (6)	0.001 (5)	−0.018 (6)	0.008 (5)

Geometric parameters (Å, º)

Au1—C1	2.057 (8)	C4—C5	1.406 (15)
Au1—N1	2.069 (7)	C4—H4	0.9500
Au1—Cl1	2.270 (2)	C5—C6	1.388 (12)
Au1—Cl2	2.414 (2)	C5—H5	0.9500
N1—C8	1.492 (11)	C6—C7	1.495 (13)
N1—H1A	0.9200	C7—C8	1.533 (14)
N1—H1B	0.9200	C7—H7A	0.9900
C1—C6	1.387 (13)	C7—H7B	0.9900
C1—C2	1.389 (13)	C8—C9	1.491 (15)
C2—C3	1.398 (15)	C8—H8	1.0000
C2—H2	0.9500	C9—H9A	0.9800
C3—C4	1.365 (17)	C9—H9B	0.9800
C3—H3	0.9500	C9—H9C	0.9800
C1—Au1—N1	92.8 (3)	C6—C5—C4	120.5 (10)
C1—Au1—Cl1	91.2 (3)	C6—C5—H5	119.7
N1—Au1—Cl1	175.4 (2)	C4—C5—H5	119.7
C1—Au1—Cl2	177.8 (3)	C1—C6—C5	117.7 (9)
N1—Au1—Cl2	85.0 (2)	C1—C6—C7	123.4 (8)
Cl1—Au1—Cl2	91.01 (9)	C5—C6—C7	118.7 (9)
C8—N1—Au1	121.6 (6)	C6—C7—C8	111.0 (8)
C8—N1—H1A	106.9	C6—C7—H7A	109.4
Au1—N1—H1A	106.9	C8—C7—H7A	109.4
C8—N1—H1B	106.9	C6—C7—H7B	109.4
Au1—N1—H1B	106.9	C8—C7—H7B	109.4
H1A—N1—H1B	106.7	H7A—C7—H7B	108.0
C6—C1—C2	123.1 (8)	C9—C8—N1	110.2 (9)
C6—C1—Au1	117.7 (6)	C9—C8—C7	114.1 (8)
C2—C1—Au1	119.2 (7)	N1—C8—C7	109.1 (8)
C1—C2—C3	117.5 (10)	C9—C8—H8	107.8
C1—C2—H2	121.2	N1—C8—H8	107.8
C3—C2—H2	121.2	C7—C8—H8	107.8
C4—C3—C2	121.2 (9)	C8—C9—H9A	109.5
C4—C3—H3	119.4	C8—C9—H9B	109.5
C2—C3—H3	119.4	H9A—C9—H9B	109.5
C3—C4—C5	120.0 (9)	C8—C9—H9C	109.5
C3—C4—H4	120.0	H9A—C9—H9C	109.5
C5—C4—H4	120.0	H9B—C9—H9C	109.5
C1—Au1—N1—C8	13.9 (7)	Au1—C1—C6—C5	178.5 (7)
Cl2—Au1—N1—C8	−166.1 (7)	C2—C1—C6—C7	−174.5 (9)
N1—Au1—C1—C6	−32.9 (7)	Au1—C1—C6—C7	3.2 (12)
Cl1—Au1—C1—C6	144.8 (7)	C4—C5—C6—C1	−0.4 (14)
N1—Au1—C1—C2	145.0 (7)	C4—C5—C6—C7	175.1 (9)
Cl1—Au1—C1—C2	−37.4 (7)	C1—C6—C7—C8	57.1 (12)
C6—C1—C2—C3	−0.6 (14)	C5—C6—C7—C8	−118.1 (9)
Au1—C1—C2—C3	−178.2 (7)	Au1—N1—C8—C9	−93.5 (9)
C1—C2—C3—C4	−0.1 (15)	Au1—N1—C8—C7	32.4 (10)
C2—C3—C4—C5	0.5 (16)	C6—C7—C8—C9	49.9 (11)
C3—C4—C5—C6	−0.2 (16)	C6—C7—C8—N1	−73.7 (10)
C2—C1—C6—C5	0.8 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl2^i	0.92	2.60	3.337 (8)	138
N1—H1B···Cl2^ii	0.92	2.56	3.404 (8)	153

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+5/2, y+1/2, z.

(II) D-Methyl(1-phenylpropan-2-yl)azanium tetrachloridoaurate(III)

Crystal data

(C10H16N)[AuCl4]	F(000) = 920
Mr = 489.00	Dx = 2.229 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2yb	Cell parameters from 9917 reflections
a = 7.3561 (1) Å	θ = 3.1–70.7°
b = 14.2394 (2) Å	µ = 25.52 mm^−1
c = 13.9103 (2) Å	T = 100 K
β = 90.077 (1)°	Parallelepiped, gold
V = 1457.05 (4) Å^3	0.24 × 0.17 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD APEXII area-detector diffractometer	4846 independent reflections
Radiation source: fine-focus sealed tube	4831 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 71.0°, θmin = 4.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −8→8
Tmin = 0.064, Tmax = 0.189	k = −16→16
13819 measured reflections	l = −15→16

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)] = 0.029	w = 1/[σ^2(Fo^2) + (0.0084P)^2 + 8.1817P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.071	(Δ/σ)max < 0.001
S = 1.15	Δρmax = 1.35 e Å^−3
4846 reflections	Δρmin = −1.50 e Å^−3
295 parameters	Extinction correction: SHELXTL (Sheldrick, 2008b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.00021 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 2131 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.077 (15)

Special details

Experimental. crystal mounted on a Cryoloop using Paratone-N

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 (Ų)

	x	y	z	Uiso*/Ueq
Au1	0.15523 (4)	0.16892 (2)	0.01409 (2)	0.01989 (11)
Cl1	0.1062 (3)	0.01049 (17)	−0.00062 (17)	0.0273 (5)
Cl2	0.1138 (3)	0.15942 (18)	0.17638 (12)	0.0284 (4)
Cl3	0.1893 (4)	0.32667 (19)	0.03219 (19)	0.0319 (5)
Cl4	0.1973 (3)	0.18108 (17)	−0.14766 (14)	0.0295 (5)
Au2	0.83880 (4)	0.14929 (2)	0.50634 (2)	0.01973 (11)
Cl5	0.9084 (3)	0.13179 (17)	0.66462 (14)	0.0282 (5)
Cl6	0.8617 (3)	−0.00867 (19)	0.48325 (19)	0.0286 (5)
Cl7	0.7724 (3)	0.17100 (18)	0.34684 (13)	0.0298 (5)
Cl8	0.8221 (3)	0.30781 (18)	0.5297 (2)	0.0300 (5)
N1	0.1540 (10)	−0.0642 (5)	0.6705 (5)	0.0251 (16)
H1C	0.1085	−0.0145	0.6359	0.030*
H1D	0.1739	−0.1128	0.6281	0.030*
C1	0.4644 (11)	−0.0100 (7)	0.6330 (6)	0.028 (2)
H1A	0.5810	0.0107	0.6617	0.033*
H1B	0.4894	−0.0677	0.5957	0.033*
C2	0.3362 (12)	−0.0352 (7)	0.7141 (6)	0.0246 (19)
H2A	0.3168	0.0218	0.7548	0.030*
C3	0.4094 (14)	−0.1125 (7)	0.7767 (7)	0.030 (2)
H3A	0.4235	−0.1698	0.7384	0.044*
H3B	0.3247	−0.1243	0.8296	0.044*
H3C	0.5278	−0.0938	0.8028	0.044*
C4	0.4020 (12)	0.0647 (7)	0.5642 (7)	0.027 (2)
C5	0.3966 (11)	0.1578 (8)	0.5933 (6)	0.031 (2)
H5	0.4348	0.1741	0.6564	0.037*
C6	0.3344 (13)	0.2291 (8)	0.5298 (9)	0.033 (2)
H6	0.3292	0.2928	0.5499	0.039*
C7	0.2828 (12)	0.2042 (7)	0.4399 (7)	0.030 (2)
H7	0.2405	0.2518	0.3975	0.035*
C8	0.2886 (13)	0.1133 (7)	0.4070 (7)	0.026 (2)
H8	0.2527	0.0980	0.3432	0.032*
C9	0.3493 (12)	0.0443 (8)	0.4708 (7)	0.028 (2)
H9	0.3547	−0.0190	0.4494	0.034*
C10	0.0133 (13)	−0.0947 (9)	0.7418 (7)	0.029 (2)
H10A	0.0379	−0.1594	0.7619	0.043*
H10B	−0.1074	−0.0914	0.7120	0.043*
H10C	0.0172	−0.0533	0.7980	0.043*
N1A	0.8383 (10)	−0.0172 (6)	0.1992 (6)	0.0317 (18)
H1G	0.8299	0.0276	0.2467	0.038*
H1H	0.8791	0.0124	0.1445	0.038*
C1A	0.5255 (12)	0.0273 (7)	0.1505 (6)	0.029 (2)
H1E	0.4035	0.0020	0.1352	0.035*
H1F	0.5122	0.0697	0.2065	0.035*
C2A	0.6496 (12)	−0.0548 (6)	0.1794 (7)	0.0241 (19)
H2B	0.6563	−0.1001	0.1246	0.029*
C3A	0.5806 (13)	−0.1055 (8)	0.2660 (7)	0.031 (2)
H3D	0.5862	−0.0637	0.3220	0.046*
H3E	0.6559	−0.1611	0.2779	0.046*
H3F	0.4544	−0.1249	0.2551	0.046*
C4A	0.5913 (12)	0.0846 (7)	0.0653 (7)	0.026 (2)
C5A	0.6010 (13)	0.0448 (8)	−0.0249 (7)	0.031 (2)
H5A	0.5675	−0.0190	−0.0343	0.038*
C6A	0.6597 (14)	0.0984 (8)	−0.1013 (9)	0.033 (2)
H6A	0.6656	0.0705	−0.1632	0.040*
C7A	0.7093 (13)	0.1895 (8)	−0.0909 (7)	0.033 (2)
H7A	0.7506	0.2243	−0.1448	0.039*
C8A	0.6993 (14)	0.2321 (8)	0.0002 (8)	0.037 (3)
H8A	0.7302	0.2964	0.0088	0.045*
C9A	0.6427 (13)	0.1774 (8)	0.0772 (7)	0.033 (2)
H9A	0.6392	0.2043	0.1396	0.040*
C10A	0.9776 (14)	−0.0880 (9)	0.2292 (8)	0.031 (2)
H10F	1.0978	−0.0583	0.2308	0.047*
H11E	0.9787	−0.1400	0.1832	0.047*
H12D	0.9477	−0.1119	0.2933	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.01938 (16)	0.0224 (2)	0.01785 (16)	0.00090 (14)	−0.00045 (11)	0.00078 (14)
Cl1	0.0270 (10)	0.0229 (12)	0.0320 (12)	−0.0032 (10)	−0.0005 (9)	0.0003 (10)
Cl2	0.0312 (10)	0.0355 (12)	0.0186 (8)	−0.0013 (11)	0.0029 (7)	−0.0012 (11)
Cl3	0.0397 (13)	0.0226 (13)	0.0333 (13)	−0.0015 (10)	0.0029 (11)	−0.0019 (11)
Cl4	0.0336 (11)	0.0373 (13)	0.0177 (9)	0.0028 (10)	0.0016 (7)	0.0022 (10)
Au2	0.01885 (16)	0.0224 (2)	0.01797 (16)	−0.00004 (14)	0.00050 (10)	0.00034 (14)
Cl5	0.0307 (10)	0.0347 (12)	0.0193 (9)	−0.0005 (9)	−0.0051 (7)	0.0036 (9)
Cl6	0.0255 (11)	0.0252 (13)	0.0350 (13)	0.0032 (9)	−0.0004 (9)	−0.0008 (11)
Cl7	0.0322 (10)	0.0396 (13)	0.0177 (9)	0.0010 (10)	−0.0015 (7)	0.0013 (11)
Cl8	0.0387 (13)	0.0205 (12)	0.0307 (13)	−0.0007 (10)	−0.0024 (10)	0.0012 (11)
N1	0.024 (4)	0.030 (4)	0.022 (4)	−0.002 (3)	0.002 (3)	0.001 (3)
C1	0.018 (4)	0.043 (6)	0.022 (5)	0.000 (4)	−0.002 (3)	0.000 (4)
C2	0.025 (4)	0.031 (5)	0.018 (5)	−0.006 (4)	0.000 (4)	0.000 (4)
C3	0.037 (5)	0.034 (6)	0.018 (5)	0.002 (4)	−0.001 (4)	0.001 (4)
C4	0.012 (4)	0.041 (6)	0.028 (5)	−0.003 (4)	−0.007 (4)	0.002 (4)
C5	0.032 (4)	0.030 (6)	0.031 (5)	0.005 (5)	−0.006 (3)	−0.001 (5)
C6	0.025 (5)	0.032 (6)	0.041 (6)	0.009 (4)	0.008 (4)	0.008 (5)
C7	0.022 (4)	0.039 (6)	0.027 (6)	−0.002 (4)	−0.008 (4)	0.010 (4)
C8	0.025 (5)	0.048 (6)	0.006 (4)	−0.010 (4)	0.000 (3)	0.007 (4)
C9	0.028 (5)	0.043 (6)	0.014 (5)	−0.005 (4)	−0.006 (4)	−0.002 (4)
C10	0.031 (6)	0.032 (6)	0.024 (6)	−0.004 (4)	0.008 (4)	0.004 (4)
N1A	0.025 (4)	0.036 (5)	0.033 (5)	0.000 (3)	−0.005 (3)	0.006 (4)
C1A	0.024 (4)	0.043 (6)	0.021 (5)	0.005 (4)	−0.004 (3)	−0.005 (4)
C2A	0.025 (5)	0.028 (5)	0.019 (5)	−0.002 (4)	0.003 (4)	−0.008 (4)
C3A	0.030 (5)	0.045 (6)	0.018 (5)	0.002 (4)	0.003 (4)	−0.003 (4)
C4A	0.016 (4)	0.038 (6)	0.024 (5)	0.005 (4)	0.000 (4)	0.000 (4)
C5A	0.026 (5)	0.033 (6)	0.035 (6)	0.009 (4)	−0.004 (4)	−0.001 (5)
C6A	0.028 (5)	0.037 (6)	0.034 (6)	0.003 (4)	0.008 (4)	0.009 (5)
C7A	0.022 (5)	0.048 (6)	0.028 (5)	0.002 (4)	0.013 (4)	0.002 (5)
C8A	0.027 (5)	0.032 (6)	0.054 (7)	−0.010 (5)	0.007 (5)	−0.004 (5)
C9A	0.032 (5)	0.031 (6)	0.036 (5)	0.006 (5)	−0.017 (4)	−0.008 (5)
C10A	0.027 (5)	0.036 (6)	0.029 (6)	0.000 (4)	−0.008 (4)	−0.004 (5)

Geometric parameters (Å, º)

Au1—Cl3	2.274 (3)	C9—H9	0.9500
Au1—Cl4	2.2782 (19)	C10—H10A	0.9800
Au1—Cl2	2.2825 (18)	C10—H10B	0.9800
Au1—Cl1	2.294 (2)	C10—H10C	0.9800
Au2—Cl5	2.2736 (19)	N1A—C10A	1.497 (13)
Au2—Cl6	2.278 (3)	N1A—C2A	1.513 (11)
Au2—Cl8	2.284 (3)	N1A—H1G	0.9200
Au2—Cl7	2.2921 (18)	N1A—H1H	0.9201
N1—C10	1.498 (12)	C1A—C4A	1.520 (13)
N1—C2	1.528 (11)	C1A—C2A	1.537 (13)
N1—H1C	0.9199	C1A—H1E	0.9900
N1—H1D	0.9200	C1A—H1F	0.9900
C1—C4	1.502 (13)	C2A—C3A	1.494 (13)
C1—C2	1.514 (12)	C2A—H2B	1.0000
C1—H1A	0.9900	C3A—H3D	0.9800
C1—H1B	0.9900	C3A—H3E	0.9800
C2—C3	1.503 (13)	C3A—H3F	0.9800
C2—H2A	1.0000	C4A—C5A	1.379 (14)
C3—H3A	0.9800	C4A—C9A	1.384 (15)
C3—H3B	0.9800	C5A—C6A	1.377 (15)
C3—H3C	0.9800	C5A—H5A	0.9500
C4—C9	1.386 (13)	C6A—C7A	1.355 (15)
C4—C5	1.387 (15)	C6A—H6A	0.9500
C5—C6	1.421 (14)	C7A—C8A	1.407 (15)
C5—H5	0.9500	C7A—H7A	0.9500
C6—C7	1.354 (15)	C8A—C9A	1.389 (15)
C6—H6	0.9500	C8A—H8A	0.9500
C7—C8	1.373 (14)	C9A—H9A	0.9500
C7—H7	0.9500	C10A—H10F	0.9800
C8—C9	1.397 (14)	C10A—H11E	0.9800
C8—H8	0.9500	C10A—H12D	0.9800
Cl3—Au1—Cl4	91.09 (9)	N1—C10—H10A	109.5
Cl3—Au1—Cl2	87.93 (9)	N1—C10—H10B	109.5
Cl4—Au1—Cl2	179.02 (10)	H10A—C10—H10B	109.5
Cl3—Au1—Cl1	177.03 (9)	N1—C10—H10C	109.5
Cl4—Au1—Cl1	90.48 (9)	H10A—C10—H10C	109.5
Cl2—Au1—Cl1	90.50 (9)	H10B—C10—H10C	109.5
Cl5—Au2—Cl6	90.67 (9)	C10A—N1A—C2A	116.1 (8)
Cl5—Au2—Cl8	88.99 (9)	C10A—N1A—H1G	108.2
Cl6—Au2—Cl8	178.83 (9)	C2A—N1A—H1G	108.3
Cl5—Au2—Cl7	178.39 (9)	C10A—N1A—H1H	108.3
Cl6—Au2—Cl7	90.71 (9)	C2A—N1A—H1H	108.2
Cl8—Au2—Cl7	89.61 (9)	H1G—N1A—H1H	107.4
C10—N1—C2	115.0 (7)	C4A—C1A—C2A	115.0 (8)
C10—N1—H1C	108.6	C4A—C1A—H1E	108.5
C2—N1—H1C	108.5	C2A—C1A—H1E	108.5
C10—N1—H1D	108.5	C4A—C1A—H1F	108.5
C2—N1—H1D	108.5	C2A—C1A—H1F	108.5
H1C—N1—H1D	107.5	H1E—C1A—H1F	107.5
C4—C1—C2	116.9 (8)	C3A—C2A—N1A	109.7 (8)
C4—C1—H1A	108.1	C3A—C2A—C1A	112.1 (8)
C2—C1—H1A	108.1	N1A—C2A—C1A	108.8 (7)
C4—C1—H1B	108.1	C3A—C2A—H2B	108.7
C2—C1—H1B	108.1	N1A—C2A—H2B	108.7
H1A—C1—H1B	107.3	C1A—C2A—H2B	108.7
C3—C2—C1	112.5 (8)	C2A—C3A—H3D	109.5
C3—C2—N1	110.2 (8)	C2A—C3A—H3E	109.5
C1—C2—N1	108.4 (7)	H3D—C3A—H3E	109.5
C3—C2—H2A	108.6	C2A—C3A—H3F	109.5
C1—C2—H2A	108.6	H3D—C3A—H3F	109.5
N1—C2—H2A	108.6	H3E—C3A—H3F	109.5
C2—C3—H3A	109.5	C5A—C4A—C9A	119.1 (10)
C2—C3—H3B	109.5	C5A—C4A—C1A	120.4 (9)
H3A—C3—H3B	109.5	C9A—C4A—C1A	120.5 (9)
C2—C3—H3C	109.5	C6A—C5A—C4A	119.4 (11)
H3A—C3—H3C	109.5	C6A—C5A—H5A	120.3
H3B—C3—H3C	109.5	C4A—C5A—H5A	120.3
C9—C4—C5	117.7 (9)	C7A—C6A—C5A	122.2 (12)
C9—C4—C1	122.3 (9)	C7A—C6A—H6A	118.9
C5—C4—C1	120.0 (8)	C5A—C6A—H6A	118.9
C4—C5—C6	120.7 (9)	C6A—C7A—C8A	119.7 (11)
C4—C5—H5	119.6	C6A—C7A—H7A	120.2
C6—C5—H5	119.6	C8A—C7A—H7A	120.2
C7—C6—C5	118.5 (10)	C9A—C8A—C7A	117.9 (10)
C7—C6—H6	120.8	C9A—C8A—H8A	121.1
C5—C6—H6	120.8	C7A—C8A—H8A	121.1
C6—C7—C8	123.1 (9)	C4A—C9A—C8A	121.7 (10)
C6—C7—H7	118.5	C4A—C9A—H9A	119.1
C8—C7—H7	118.5	C8A—C9A—H9A	119.1
C7—C8—C9	117.5 (9)	N1A—C10A—H10F	109.5
C7—C8—H8	121.3	N1A—C10A—H11E	109.5
C9—C8—H8	121.3	H10F—C10A—H11E	109.5
C4—C9—C8	122.5 (10)	N1A—C10A—H12D	109.5
C4—C9—H9	118.8	H10F—C10A—H12D	109.5
C8—C9—H9	118.8	H11E—C10A—H12D	109.5
C4—C1—C2—C3	178.2 (8)	C10A—N1A—C2A—C3A	56.7 (10)
C4—C1—C2—N1	56.1 (11)	C10A—N1A—C2A—C1A	179.6 (8)
C10—N1—C2—C3	54.5 (11)	C4A—C1A—C2A—C3A	177.6 (8)
C10—N1—C2—C1	178.0 (9)	C4A—C1A—C2A—N1A	56.1 (10)
C2—C1—C4—C9	−108.0 (11)	C2A—C1A—C4A—C5A	65.8 (11)
C2—C1—C4—C5	72.3 (11)	C2A—C1A—C4A—C9A	−114.0 (10)
C9—C4—C5—C6	1.6 (13)	C9A—C4A—C5A—C6A	−0.7 (14)
C1—C4—C5—C6	−178.7 (8)	C1A—C4A—C5A—C6A	179.5 (9)
C4—C5—C6—C7	−0.8 (14)	C4A—C5A—C6A—C7A	0.2 (16)
C5—C6—C7—C8	−0.4 (15)	C5A—C6A—C7A—C8A	−0.8 (16)
C6—C7—C8—C9	0.7 (15)	C6A—C7A—C8A—C9A	1.7 (15)
C5—C4—C9—C8	−1.3 (14)	C5A—C4A—C9A—C8A	1.7 (14)
C1—C4—C9—C8	179.0 (9)	C1A—C4A—C9A—C8A	−178.5 (9)
C7—C8—C9—C4	0.2 (14)	C7A—C8A—C9A—C4A	−2.2 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···Cl5^i	0.92	2.58	3.324 (8)	138
N1—H1C···Cl6^i	0.92	2.79	3.465 (8)	131
N1—H1D···Cl8^ii	0.92	2.47	3.334 (8)	156
N1A—H1G···Cl7	0.92	2.51	3.410 (9)	167
N1A—H1H···Cl1^iii	0.92	2.62	3.432 (9)	147
N1A—H1H···Cl2^iii	0.92	2.75	3.244 (8)	115

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

(III) D,L-(1-Hydroxy-1-phenylpropan-2-yl)(methyl)azanium tetrachloridoaurate(III)

Crystal data

(C10H16NO)[AuCl4]	F(000) = 1904
Mr = 505.00	Dx = 2.242 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 9963 reflections
a = 7.7537 (4) Å	θ = 3.4–71.9°
b = 25.0264 (13) Å	µ = 24.93 mm^−1
c = 15.4587 (8) Å	T = 100 K
β = 93.920 (2)°	Needle, yellow
V = 2992.7 (3) Å^3	0.38 × 0.11 × 0.06 mm
Z = 8

Data collection

Bruker SMART CCD APEXII area-detector diffractometer	5386 independent reflections
Radiation source: fine-focus sealed tube	4874 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
φ and ω scans	θmax = 72.1°, θmin = 3.4°
Absorption correction: numerical (SADABS; Sheldrick, 2008a)	h = −9→7
Tmin = 0.038, Tmax = 0.326	k = −29→29
26603 measured reflections	l = −18→18

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) = 0.094	w = 1/[σ^2(Fo^2) + (0.0328P)^2 + 25.1429P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
5386 reflections	Δρmax = 1.94 e Å^−3
312 parameters	Δρmin = −1.35 e Å^−3
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.000023 (9)

Special details

Experimental. crystal mounted on a Cryoloop using Paratone-N

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 (Ų)

	x	y	z	Uiso*/Ueq
Au1	0.51006 (4)	0.076623 (12)	0.056401 (19)	0.02202 (11)
Cl1	0.2212 (2)	0.09400 (9)	0.05762 (13)	0.0325 (4)
Cl2	0.4833 (2)	0.06536 (8)	−0.09056 (12)	0.0290 (4)
Cl3	0.8006 (2)	0.06545 (8)	0.05363 (13)	0.0303 (4)
Cl4	0.5373 (3)	0.08461 (9)	0.20336 (13)	0.0366 (5)
Au2	0.48945 (4)	0.012413 (13)	0.62846 (2)	0.02478 (11)
Cl5	0.5179 (2)	−0.07059 (7)	0.56997 (12)	0.0276 (4)
Cl6	0.1954 (3)	0.00565 (9)	0.61780 (16)	0.0412 (5)
Cl7	0.4660 (3)	0.09502 (8)	0.68776 (14)	0.0361 (5)
Cl8	0.7820 (2)	0.02260 (8)	0.63758 (13)	0.0330 (4)
O1	0.0588 (7)	0.3790 (2)	0.2068 (4)	0.0324 (13)
H1	0.1164	0.4055	0.1919	0.049*
N1	−0.1352 (8)	0.4183 (3)	0.3320 (4)	0.0269 (14)
H1B	−0.1719	0.4217	0.2744	0.032*
H1C	−0.2318	0.4189	0.3634	0.032*
C1	0.1119 (10)	0.3647 (3)	0.2937 (5)	0.0292 (18)
H1D	0.1934	0.3926	0.3183	0.035*
C2	−0.0498 (10)	0.3651 (3)	0.3448 (5)	0.0254 (17)
H2A	−0.0147	0.3603	0.4078	0.030*
C3	−0.1829 (11)	0.3225 (3)	0.3169 (7)	0.040 (2)
H3A	−0.2860	0.3271	0.3494	0.060*
H3B	−0.1335	0.2870	0.3287	0.060*
H3C	−0.2145	0.3260	0.2547	0.060*
C4	0.2038 (10)	0.3109 (3)	0.2987 (5)	0.0283 (18)
C5	0.2999 (11)	0.2966 (4)	0.3742 (6)	0.0345 (19)
H5	0.3056	0.3199	0.4228	0.041*
C6	0.3883 (12)	0.2478 (4)	0.3791 (6)	0.042 (2)
H6	0.4517	0.2379	0.4314	0.051*
C7	0.3840 (12)	0.2144 (4)	0.3092 (6)	0.040 (2)
H7	0.4469	0.1818	0.3122	0.048*
C8	0.2872 (12)	0.2283 (3)	0.2339 (6)	0.038 (2)
H8	0.2825	0.2049	0.1854	0.045*
C9	0.1974 (11)	0.2762 (3)	0.2289 (6)	0.0332 (19)
H9	0.1309	0.2853	0.1772	0.040*
C10	−0.0258 (11)	0.4658 (3)	0.3574 (6)	0.0327 (19)
H10D	0.0403	0.4585	0.4124	0.049*
H10E	−0.1001	0.4970	0.3641	0.049*
H10F	0.0540	0.4729	0.3123	0.049*
O1A	1.1608 (12)	0.1516 (4)	0.5115 (6)	0.083 (3)
H2	1.1821	0.1451	0.5645	0.124*
N1A	1.0668 (9)	0.1027 (3)	0.3631 (4)	0.0312 (15)
H1E	1.1788	0.1047	0.3868	0.037*
H1F	1.0189	0.0721	0.3843	0.037*
C1A	0.9824 (12)	0.1485 (4)	0.4914 (6)	0.041 (2)
H1A	0.9367	0.1137	0.5120	0.049*
C2A	0.9778 (16)	0.1493 (6)	0.3966 (7)	0.080 (5)
H2A1	1.0607	0.1788	0.3858	0.095*
C3A	0.8167 (17)	0.1673 (6)	0.3433 (8)	0.108 (7)
H3A1	0.7355	0.1374	0.3361	0.162*
H3A2	0.8484	0.1794	0.2863	0.162*
H3A3	0.7622	0.1967	0.3732	0.162*
C4A	0.8854 (12)	0.1950 (4)	0.5298 (6)	0.038 (2)
C5A	0.7302 (13)	0.1846 (4)	0.5637 (6)	0.046 (2)
H5A	0.6847	0.1493	0.5625	0.055*
C6A	0.6381 (15)	0.2266 (5)	0.6005 (6)	0.057 (3)
H6A	0.5310	0.2195	0.6246	0.069*
C7A	0.7027 (17)	0.2772 (5)	0.6012 (7)	0.058 (3)
H7A	0.6402	0.3056	0.6253	0.070*
C8A	0.8593 (16)	0.2870 (4)	0.5670 (6)	0.055 (3)
H8A	0.9042	0.3224	0.5678	0.066*
C9A	0.9511 (14)	0.2465 (4)	0.5317 (6)	0.049 (3)
H9A	1.0592	0.2537	0.5087	0.059*
C10A	1.0723 (14)	0.0971 (4)	0.2677 (6)	0.046 (2)
H10A	0.9615	0.0831	0.2432	0.069*
H10B	1.1653	0.0724	0.2548	0.069*
H10C	1.0938	0.1321	0.2422	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.02034 (18)	0.02480 (18)	0.02078 (18)	−0.00058 (11)	0.00045 (11)	0.00126 (12)
Cl1	0.0216 (10)	0.0474 (12)	0.0285 (10)	0.0007 (8)	0.0026 (7)	0.0019 (9)
Cl2	0.0229 (10)	0.0443 (11)	0.0196 (9)	−0.0003 (7)	−0.0001 (7)	−0.0013 (8)
Cl3	0.0212 (10)	0.0377 (11)	0.0317 (10)	0.0037 (7)	−0.0012 (7)	0.0019 (8)
Cl4	0.0351 (12)	0.0518 (13)	0.0227 (10)	0.0027 (9)	−0.0001 (8)	−0.0020 (9)
Au2	0.02086 (18)	0.03138 (19)	0.02224 (18)	−0.00393 (12)	0.00258 (12)	−0.00216 (13)
Cl5	0.0284 (10)	0.0288 (9)	0.0252 (9)	−0.0024 (7)	−0.0015 (7)	−0.0014 (8)
Cl6	0.0224 (11)	0.0422 (12)	0.0601 (15)	−0.0045 (8)	0.0111 (9)	−0.0105 (11)
Cl7	0.0334 (11)	0.0370 (11)	0.0387 (12)	−0.0062 (8)	0.0087 (8)	−0.0130 (9)
Cl8	0.0199 (10)	0.0439 (12)	0.0348 (11)	−0.0044 (8)	−0.0012 (7)	−0.0055 (9)
O1	0.033 (3)	0.035 (3)	0.029 (3)	0.003 (2)	−0.001 (2)	0.005 (3)
N1	0.024 (4)	0.031 (4)	0.025 (4)	0.001 (3)	0.000 (3)	−0.005 (3)
C1	0.029 (5)	0.032 (4)	0.025 (4)	−0.002 (3)	−0.004 (3)	−0.001 (4)
C2	0.025 (4)	0.025 (4)	0.025 (4)	0.002 (3)	−0.007 (3)	0.001 (3)
C3	0.027 (5)	0.034 (5)	0.059 (6)	0.000 (4)	−0.002 (4)	−0.001 (4)
C4	0.020 (4)	0.036 (5)	0.029 (4)	0.002 (3)	0.005 (3)	0.001 (4)
C5	0.035 (5)	0.035 (5)	0.034 (5)	−0.001 (4)	−0.001 (4)	−0.006 (4)
C6	0.041 (6)	0.042 (5)	0.043 (6)	0.006 (4)	−0.006 (4)	0.005 (5)
C7	0.035 (5)	0.030 (5)	0.057 (6)	0.002 (4)	0.017 (4)	0.006 (4)
C8	0.046 (6)	0.031 (5)	0.038 (5)	0.002 (4)	0.018 (4)	0.000 (4)
C9	0.031 (5)	0.035 (5)	0.034 (5)	−0.003 (3)	0.006 (3)	0.005 (4)
C10	0.035 (5)	0.029 (4)	0.035 (5)	0.001 (3)	0.000 (4)	−0.001 (4)
O1A	0.076 (6)	0.086 (7)	0.084 (7)	0.011 (5)	−0.012 (5)	−0.034 (5)
N1A	0.030 (4)	0.036 (4)	0.027 (4)	0.001 (3)	−0.001 (3)	−0.005 (3)
C1A	0.039 (6)	0.053 (6)	0.031 (5)	0.011 (4)	−0.002 (4)	−0.004 (4)
C2A	0.096 (10)	0.103 (11)	0.036 (6)	0.067 (8)	−0.019 (6)	−0.019 (7)
C3A	0.166 (17)	0.112 (13)	0.046 (8)	0.097 (12)	−0.003 (9)	0.000 (8)
C4A	0.045 (6)	0.040 (5)	0.029 (5)	0.008 (4)	−0.001 (4)	−0.006 (4)
C5A	0.050 (6)	0.058 (6)	0.030 (5)	0.008 (5)	−0.003 (4)	−0.005 (5)
C6A	0.063 (7)	0.080 (9)	0.030 (5)	0.030 (6)	0.011 (5)	−0.002 (5)
C7A	0.086 (9)	0.057 (7)	0.032 (6)	0.035 (6)	−0.003 (5)	−0.006 (5)
C8A	0.091 (9)	0.038 (6)	0.034 (6)	0.016 (5)	−0.011 (5)	0.004 (5)
C9A	0.058 (7)	0.057 (7)	0.033 (5)	0.015 (5)	0.003 (4)	0.003 (5)
C10A	0.064 (7)	0.050 (6)	0.025 (5)	0.003 (5)	0.008 (4)	−0.002 (4)

Geometric parameters (Å, º)

Au1—Cl3	2.2734 (18)	C9—H9	0.9500
Au1—Cl4	2.276 (2)	C10—H10D	0.9800
Au1—Cl1	2.2831 (19)	C10—H10E	0.9800
Au1—Cl2	2.2846 (18)	C10—H10F	0.9800
Au2—Cl7	2.274 (2)	O1A—C1A	1.399 (12)
Au2—Cl8	2.2776 (19)	O1A—H2	0.8399
Au2—Cl6	2.281 (2)	N1A—C2A	1.468 (12)
Au2—Cl5	2.2823 (19)	N1A—C10A	1.485 (11)
O1—C1	1.423 (9)	N1A—H1E	0.9200
O1—H1	0.8399	N1A—H1F	0.9199
N1—C2	1.495 (10)	C1A—C2A	1.463 (14)
N1—C10	1.495 (10)	C1A—C4A	1.527 (12)
N1—H1B	0.9200	C1A—H1A	1.0000
N1—H1C	0.9200	C2A—C3A	1.517 (2)
C1—C4	1.522 (11)	C2A—H2A1	1.0000
C1—C2	1.528 (11)	C3A—H3A1	0.9800
C1—H1D	1.0000	C3A—H3A2	0.9800
C2—C3	1.525 (11)	C3A—H3A3	0.9800
C2—H2A	1.0000	C4A—C5A	1.370 (14)
C3—H3A	0.9800	C4A—C9A	1.385 (15)
C3—H3B	0.9800	C5A—C6A	1.411 (14)
C3—H3C	0.9800	C5A—H5A	0.9500
C4—C9	1.383 (12)	C6A—C7A	1.362 (17)
C4—C5	1.388 (12)	C6A—H6A	0.9500
C5—C6	1.399 (13)	C7A—C8A	1.379 (17)
C5—H5	0.9500	C7A—H7A	0.9500
C6—C7	1.364 (13)	C8A—C9A	1.374 (14)
C6—H6	0.9500	C8A—H8A	0.9500
C7—C8	1.386 (13)	C9A—H9A	0.9500
C7—H7	0.9500	C10A—H10A	0.9800
C8—C9	1.386 (12)	C10A—H10B	0.9800
C8—H8	0.9500	C10A—H10C	0.9800
Cl5···Au2^i	3.3924 (19)
Cl3—Au1—Cl4	90.29 (7)	N1—C10—H10D	109.5
Cl3—Au1—Cl1	176.04 (7)	N1—C10—H10E	109.5
Cl4—Au1—Cl1	89.96 (7)	H10D—C10—H10E	109.5
Cl3—Au1—Cl2	89.36 (7)	N1—C10—H10F	109.5
Cl4—Au1—Cl2	177.95 (8)	H10D—C10—H10F	109.5
Cl1—Au1—Cl2	90.53 (7)	H10E—C10—H10F	109.5
Cl7—Au2—Cl8	88.86 (7)	C1A—O1A—H2	109.4
Cl7—Au2—Cl6	89.39 (8)	C2A—N1A—C10A	118.1 (8)
Cl8—Au2—Cl6	177.75 (8)	C2A—N1A—H1E	105.6
Cl7—Au2—Cl5	178.99 (7)	C10A—N1A—H1E	108.1
Cl8—Au2—Cl5	90.21 (7)	C2A—N1A—H1F	108.9
Cl6—Au2—Cl5	91.55 (7)	C10A—N1A—H1F	108.4
C1—O1—H1	109.4	H1E—N1A—H1F	107.3
C2—N1—C10	115.8 (6)	O1A—C1A—C2A	100.2 (9)
C2—N1—H1B	108.3	O1A—C1A—C4A	112.1 (8)
C10—N1—H1B	108.3	C2A—C1A—C4A	113.6 (8)
C2—N1—H1C	108.3	O1A—C1A—H1A	110.2
C10—N1—H1C	108.4	C2A—C1A—H1A	110.2
H1B—N1—H1C	107.4	C4A—C1A—H1A	110.2
O1—C1—C4	112.0 (7)	C1A—C2A—N1A	111.3 (9)
O1—C1—C2	107.0 (6)	C1A—C2A—C3A	120.7 (10)
C4—C1—C2	112.1 (7)	N1A—C2A—C3A	115.7 (9)
O1—C1—H1D	108.5	C1A—C2A—H2A1	101.8
C4—C1—H1D	108.5	N1A—C2A—H2A1	101.8
C2—C1—H1D	108.5	C3A—C2A—H2A1	101.8
N1—C2—C3	107.5 (6)	C2A—C3A—H3A1	109.5
N1—C2—C1	108.0 (6)	C2A—C3A—H3A2	109.5
C3—C2—C1	114.3 (7)	H3A1—C3A—H3A2	109.5
N1—C2—H2A	109.0	C2A—C3A—H3A3	109.5
C3—C2—H2A	109.0	H3A1—C3A—H3A3	109.5
C1—C2—H2A	109.0	H3A2—C3A—H3A3	109.5
C2—C3—H3A	109.5	C5A—C4A—C9A	120.0 (9)
C2—C3—H3B	109.5	C5A—C4A—C1A	118.2 (9)
H3A—C3—H3B	109.5	C9A—C4A—C1A	121.8 (9)
C2—C3—H3C	109.5	C4A—C5A—C6A	119.7 (11)
H3A—C3—H3C	109.5	C4A—C5A—H5A	120.2
H3B—C3—H3C	109.5	C6A—C5A—H5A	120.2
C9—C4—C5	118.8 (8)	C7A—C6A—C5A	120.0 (11)
C9—C4—C1	121.6 (7)	C7A—C6A—H6A	120.0
C5—C4—C1	119.6 (7)	C5A—C6A—H6A	120.0
C4—C5—C6	120.2 (8)	C6A—C7A—C8A	119.8 (10)
C4—C5—H5	119.9	C6A—C7A—H7A	120.1
C6—C5—H5	119.9	C8A—C7A—H7A	120.1
C7—C6—C5	120.4 (9)	C9A—C8A—C7A	120.9 (11)
C7—C6—H6	119.8	C9A—C8A—H8A	119.6
C5—C6—H6	119.8	C7A—C8A—H8A	119.6
C6—C7—C8	119.6 (9)	C8A—C9A—C4A	119.7 (11)
C6—C7—H7	120.2	C8A—C9A—H9A	120.1
C8—C7—H7	120.2	C4A—C9A—H9A	120.1
C7—C8—C9	120.3 (9)	N1A—C10A—H10A	109.5
C7—C8—H8	119.9	N1A—C10A—H10B	109.5
C9—C8—H8	119.9	H10A—C10A—H10B	109.5
C4—C9—C8	120.6 (9)	N1A—C10A—H10C	109.5
C4—C9—H9	119.7	H10A—C10A—H10C	109.5
C8—C9—H9	119.7	H10B—C10A—H10C	109.5
C10—N1—C2—C3	179.0 (7)	O1A—C1A—C2A—N1A	62.5 (13)
C10—N1—C2—C1	−57.2 (8)	C4A—C1A—C2A—N1A	−177.7 (9)
O1—C1—C2—N1	−53.9 (8)	O1A—C1A—C2A—C3A	−156.8 (14)
C4—C1—C2—N1	−177.1 (6)	C4A—C1A—C2A—C3A	−37.1 (19)
O1—C1—C2—C3	65.8 (9)	C10A—N1A—C2A—C1A	179.4 (9)
C4—C1—C2—C3	−57.4 (9)	C10A—N1A—C2A—C3A	36.6 (18)
O1—C1—C4—C9	−13.8 (11)	O1A—C1A—C4A—C5A	−140.4 (9)
C2—C1—C4—C9	106.5 (9)	C2A—C1A—C4A—C5A	106.9 (12)
O1—C1—C4—C5	164.6 (7)	O1A—C1A—C4A—C9A	39.0 (13)
C2—C1—C4—C5	−75.1 (9)	C2A—C1A—C4A—C9A	−73.7 (13)
C9—C4—C5—C6	0.0 (13)	C9A—C4A—C5A—C6A	0.0 (14)
C1—C4—C5—C6	−178.5 (8)	C1A—C4A—C5A—C6A	179.4 (9)
C4—C5—C6—C7	1.4 (14)	C4A—C5A—C6A—C7A	0.7 (15)
C5—C6—C7—C8	−1.8 (14)	C5A—C6A—C7A—C8A	−0.8 (16)
C6—C7—C8—C9	1.0 (13)	C6A—C7A—C8A—C9A	0.2 (16)
C5—C4—C9—C8	−0.8 (12)	C7A—C8A—C9A—C4A	0.5 (15)
C1—C4—C9—C8	177.6 (8)	C5A—C4A—C9A—C8A	−0.6 (15)
C7—C8—C9—C4	0.4 (13)	C1A—C4A—C9A—C8A	−180.0 (9)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl6^ii	0.84	2.59	3.399 (6)	161
O1—H1···Cl7^ii	0.84	2.72	3.256 (6)	124
N1—H1B···O1	0.92	2.38	2.716 (9)	101
N1—H1B···Cl8^iii	0.92	2.54	3.371 (7)	151
N1—H1C···Cl2^iv	0.92	2.40	3.292 (7)	163
N1A—H1E···O1A	0.92	2.27	2.658 (11)	105
N1A—H1E···Cl5^v	0.92	2.55	3.410 (7)	156
N1A—H1F···Cl6^i	0.92	2.56	3.413 (7)	155
O1A—H2···O1^vi	0.84	2.53	3.264 (12)	146

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