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The title salt, methyl (1R,2R,3S,5S,8S)-3-benzoyl­oxy-8-methyl-8-aza­bicyclo­[3.2.1]octane-2-carboxyl­ate tetra­chloro­aurate(III), (C17H22NO4)[AuCl4], has its protonated N atom intra­molecularly hydrogen bonded to the O atom of the methoxy­carbonyl group [N...O = 2.755 (6) Å and N—H...O = 136°]. Two close inter­molecular C—H...O contacts exist, as well as five C—H...Cl close contacts. The [AuCl4] anion was found to be distorted square planar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106053108/gz3036sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106053108/gz3036Isup2.hkl
Contains datablock I

CCDC reference: 638296

Comment top

Cocaine is a complex tropane alkaloid which occurs naturally in the leaves of the coca plant, Erythroxylum coca. In the United States, cocaine is one of the most widely abused illicit drugs, second only to marijuana (Drug Enforcement Administration, 2006). Pharmacologically, cocaine acts as a central nervous system stimulant, and has been used medically as a local anesthetic. The structure of cocaine was originally determined by Willstätter & Müller (1898) by chemical means and verified by a crystal structure of L-cocaine hydrochloride by Gabe & Barnes (1963); this structure was redetermined by Zhu et al. in 1999.

The gold chloride microcrystal test has been widely utilized for over 100 years (Lyons, 1885) by forensic scientists in the general scheme of analysis for cocaine. Microcrystal tests are one of the fastest and simplest techniques for differentiating L-cocaine from its seven stereoisomers (Allen et al., 1981). Unlike some of the more sophisticated techniques such as mass spectrometry, microcrystal tests are inexpensive, and the only instrument required is a light microscope. This test involves the addition of a 5% w/v solution of chloroauric acid in water (HAuCl4·3H2O) to a dilute aqueous acidified (HCl) solution of suspected cocaine, followed by observation of the resulting crystals microscopically (American Society for Testing and Materials, 2003). However, the interpretation of the resulting microcrystalline precipitate has been empirical and subject to the training and experience of the analyst (McCrone, 1992). In our study, single-crystal X-ray diffraction was used to determine the absolute configuration of the gold(III) tetrachloride salt of L-cocaine, (I), which has the same powder diffraction profile as the microcrystalline material.

Fig. 1 shows the asymmetric unit of (I). Compared with the structure reported by Zhu et al. (1999), the main difference in the cocaine cation is the rotation of the methoxycarbonyl group about the C2—C16 bond in (I). The L-cocaine–HCl structure reported by Zhu et al. (1999) has the methoxycarbonyl group rotated [torsion angle -138.4 (8)°] to allow hydrogen bonding between the protonated N atom and the methoxy O atom. In the present structure, (I), this torsion angle [C3—C2—C16—O4 = 89.9 (6)°] allows the protonated N atom to be hydrogen-bonded to the carbonyl O atom [N1···O3 = 2.755 (6) Å, and N1—H1A···O3 = 136°]. According to potential energy calculations performed by Zhu et al. (1999), the energy minimum for the methoxycarbonyl group occurs at a torsion angle of approximatelyl 95–110°. The orientation of the methoxycarbonyl group found in (I) corresponds closely to the conformation found in the structure of (-)-norcocaine (Zhu et al., 1994), which exhibits similar hydrogen bonding between the protonated atom N1 and the carbonyl atom O3.

The [AuCl4]- anion of (I) was found to be a distorted square plane, with the Au atom 0.0056 (8) Å above the best least-squares plane of the five-atom moiety. Two opposing Cl- anions are above the best plane by 0.0784 (14) Å and the other two are below the plane by -0.0812 (14) Å. In a search of the Cambridge Structural Database (CSD, Version 5.27, update of May 2006; Allen, 2002), 89 structures containing the gold tetrachloride anion are found. However, only 24 show the `bowing' of the square-planar arrangement of the Au and the four Cl- anions. Of these, only one shows flexing of the Cl- anions slightly larger than that found here. Two opposing Cl- anions in the structure of tetra(methylthio)tetrathiafulvalene bis(tetrachloro-gold) (CSD refcode GEHSOB01; Jones, 1989) are above the best plane by 0.087 Å and the opposite two are below the plane by -0.078 Å. All of the other gold tetrachloride anions are more planar than that in (I), mostly forming a very nearly perfect square-planar arrangement about the Au atom.

In (I), the hydrogen bonding between atom N1 and the O atom of the methoxycarbonyl group (O3) is characterized by N1···O3 = 2.755 (6) Å and N1—H1A···O3 = 136°. In the structure of (-)-cocaine hydrochloride (Zhu et al., 1999), there is a hydrogen bond between atom N1 and the Cl- anion [3.058 (9) Å] and another weaker hydrogen bond between atom N1 and the methoxy O atom [2.894 (9) Å]. This latter hydrogen bond is made possible because of the rotation of the methoxycarbonyl group in this structure to present the methoxy O atom to the H atom on N1. In (I), since the methoxycarbonyl group is rotated by 131.5 (10)°, this hydrogen bond from N1 is to the carbonyl atom O3.

Fig. 2 illustrates the hydrogen bonding and close contacts of (I). Two intermolecular close contacts are present (Table 1) within the 2.7 Å range that we employ as standard for non-bonded C—H···O packing interactions (Steiner, 1997). Also, four close contacts exist to three of the four Cl- of the anion; atom Cl1 has no close contacts (see Table 1). However, a symmetry-related [AuCl4]- anion is located such that the Cl1···Au1(1 - x, -1/2 + y, 3/2 - z) distance is 4.3742 (16) Å and the Au1—Cl1···Au1(1 - x, -1/2 + y, 3/2 - z) angle is 172.38 (6)°. The interplanar angle between the best least-squares planes of two [AuCl4]- anions is 82.81 (4)°, which results in a herringbone pattern of the [AuCl4]- anions, with atom Cl1 pointing directly at the Au of an adjacent anion.

Related literature top

For related literature, see: Allen (2002); Allen et al. (1981); American & Materials (2003); Drug (2006); Gabe & Barnes (1963); Jones (1989); Lyons (1885); McCrone (1992); Steiner (1997); Willstätter & Müller (1898); Zhu et al. (1994, 1999).

Experimental top

For the preparation of (I), L-cocaine hydrochloride (Sigma, lot No. 48 F0208) was dissolved in water to yield a 50 µg ml-1 solution. This solution (200 µl) was combined with 0.5% acidified (HCl) gold(III) chloride (HAuCl4·3H2O) (200 µl) and allowed to crystallize. Extremely long gold parallelepiped crystals formed (m.p. 452 K). A suitable crystal for X-ray analysis was cut from one of these long rods.

Refinement top

All H atoms for (I) were found in electron-density difference maps. The methyl H atoms were placed in ideally staggered positions, with C—H distances of 0.98 Å and Uiso(H) = 1.5Ueq(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 distances of 0.99 and 1.00 Å, respectively, and with Uiso(H) = 1.2Ueq(C). The ammonium H atom was similarly placed in an idealized position, with an N—H distance of 0.91 Å, and refined with Uiso(H) = 1.2Ueq(N).

Computing details top

Data collection: SMART (Bruker, 2006); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2004); program(s) used to refine structure: SHELXL97 (Sheldrick, 2004); molecular graphics: SHELXTL (Sheldrick, 2004); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I). Displacement ellipsoids are drawn at the 30% probability level. The [AuCl4]- counter-ion was chosen on the basis of its proximity to the site of the positive charge on N1.
[Figure 2] Fig. 2. A diagram with unit-cell axes, showing the internal hydrogen bonding (dashed line) and close contacts (thin solid lines) for (I). Displacement ellipsoids are drawn at the 30% probability level. For clarity, all C-bound H atoms have been omitted unless they are involved in the bonding. Symmetry-related molecules involved in the close contacts are shown with open bonds to simplify the drawing. The close contacts shown involve parts of five other separate asymmetric units, of which one contains both O3i and Cl4i. The [AuCl4]-1 anion of the main molecule and the non-H atoms participating in the hydrogen-bonding interactions are also labelled. [Symmetry codes: (i) x - 1, y, z; (ii) x - 1/2, 1/2 - y, 2 - z; (iii) x, 1 + y, z; (iv) x - 1, 1 + y, z; (v) 3 - x, 1/2 + y, 3/2 - z.]
(1R,2R,3S,5S,8S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate tetrachlorogold(III) top
Crystal data top
(C17H22NO4)[AuCl4]Dx = 1.953 Mg m3
Mr = 643.12Melting point: 452 K
Orthorhombic, P212121Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2abCell parameters from 14526 reflections
a = 7.7358 (3) Åθ = 3.0–68.5°
b = 9.4543 (5) ŵ = 17.33 mm1
c = 29.9093 (13) ÅT = 295 K
V = 2187.46 (17) Å3Parallelepiped, yellow
Z = 40.45 × 0.21 × 0.08 mm
F(000) = 1240
Data collection top
Bruker SMART CCD APEXII area-detector
diffractometer
3906 independent reflections
Radiation source: fine-focus sealed tube3804 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
ϕ and ω scansθmax = 68.5°, θmin = 3.0°
Absorption correction: numerical and multi-scan
[SHELXTL (Sheldrick, 2004) and SADABS (Bruker, 2005)]
h = 99
Tmin = 0.042, Tmax = 0.338k = 1111
14526 measured reflectionsl = 3634
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.070 w = 1/[σ2(Fo2) + (0.0263P)2 + 0.9351P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3906 reflectionsΔρmax = 0.59 e Å3
246 parametersΔρmin = 0.96 e Å3
0 restraintsAbsolute structure: Flack (1983), with 1468 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.025 (14)
Crystal data top
(C17H22NO4)[AuCl4]V = 2187.46 (17) Å3
Mr = 643.12Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 7.7358 (3) ŵ = 17.33 mm1
b = 9.4543 (5) ÅT = 295 K
c = 29.9093 (13) Å0.45 × 0.21 × 0.08 mm
Data collection top
Bruker SMART CCD APEXII area-detector
diffractometer
3906 independent reflections
Absorption correction: numerical and multi-scan
[SHELXTL (Sheldrick, 2004) and SADABS (Bruker, 2005)]
3804 reflections with I > 2σ(I)
Tmin = 0.042, Tmax = 0.338Rint = 0.052
14526 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.070Δρmax = 0.59 e Å3
S = 1.05Δρmin = 0.96 e Å3
3906 reflectionsAbsolute structure: Flack (1983), with 1468 Friedel pairs
246 parametersAbsolute structure parameter: 0.025 (14)
0 restraints
Special details top

Experimental. Crystal mounted on 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 (Å2) top
xyzUiso*/Ueq
Au11.48067 (3)0.08296 (2)0.827908 (6)0.04897 (9)
Cl11.4831 (3)0.26793 (18)0.77877 (5)0.0723 (4)
O10.4481 (8)0.5175 (7)0.89138 (15)0.0864 (16)
N11.1201 (7)0.4034 (5)0.83739 (15)0.0523 (10)
H1A1.16160.41360.86570.063*
C10.9621 (9)0.3070 (6)0.83835 (19)0.0570 (14)
H10.99620.20740.84010.068*
Cl21.18875 (19)0.0958 (2)0.83312 (6)0.0714 (4)
O20.7201 (6)0.5528 (5)0.91443 (13)0.0617 (10)
C20.8493 (9)0.3483 (7)0.87798 (19)0.0539 (14)
H20.74570.28870.87770.065*
Cl31.7706 (2)0.0551 (2)0.81918 (6)0.0739 (5)
C30.7920 (10)0.5049 (7)0.87294 (19)0.0602 (16)
H30.70430.51180.84940.072*
O31.0932 (7)0.3471 (7)0.92750 (16)0.0824 (16)
Cl41.4790 (3)0.0911 (2)0.88051 (6)0.0821 (4)
O40.8372 (7)0.2909 (5)0.95482 (16)0.0682 (13)
C40.9404 (9)0.5985 (6)0.86168 (18)0.0603 (15)
H4A1.01570.60690.88750.072*
H4B0.89770.69220.85440.072*
C51.0429 (10)0.5405 (6)0.82234 (17)0.0580 (14)
H51.13290.60720.81300.070*
C60.9317 (11)0.4944 (9)0.7824 (2)0.074 (2)
H6A0.99760.49890.75490.089*
H6B0.83070.55450.77960.089*
C70.8782 (12)0.3408 (10)0.7928 (2)0.079 (2)
H7A0.75340.33260.79460.095*
H7B0.92030.27690.76990.095*
C81.2631 (11)0.3534 (9)0.8075 (2)0.0745 (19)
H8A1.22210.34880.77720.112*
H8B1.30040.26120.81680.112*
H8C1.35850.41820.80920.112*
C90.5503 (9)0.5465 (6)0.92093 (18)0.0567 (14)
C100.5017 (10)0.5735 (6)0.96792 (18)0.0636 (15)
C110.3276 (12)0.5805 (9)0.9789 (2)0.0789 (19)
H110.24280.57790.95690.095*
C120.2836 (13)0.5915 (10)1.0241 (3)0.093 (3)
H120.16750.59761.03200.112*
C130.4045 (17)0.5937 (12)1.0569 (3)0.105 (4)
H130.37160.59861.08670.126*
C140.5712 (15)0.5886 (13)1.0458 (2)0.098 (3)
H140.65390.59021.06830.117*
C150.6257 (13)0.5810 (10)1.0012 (2)0.080 (2)
H150.74280.58100.99410.096*
C160.9428 (9)0.3258 (6)0.92225 (19)0.0543 (14)
C170.9164 (12)0.2851 (10)0.9998 (3)0.088 (3)
H17A1.02420.23500.99820.132*
H17B0.83980.23691.01990.132*
H17C0.93650.37951.01040.132*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au10.03817 (12)0.06238 (13)0.04636 (12)0.00480 (9)0.00432 (8)0.01037 (9)
Cl10.0674 (10)0.0800 (9)0.0696 (8)0.0057 (9)0.0116 (8)0.0080 (7)
O10.074 (4)0.133 (5)0.053 (2)0.001 (3)0.002 (2)0.009 (3)
N10.058 (3)0.059 (3)0.039 (2)0.001 (2)0.0005 (17)0.001 (2)
C10.066 (4)0.050 (2)0.056 (3)0.004 (3)0.007 (3)0.012 (2)
Cl20.0421 (7)0.0984 (11)0.0736 (9)0.0079 (8)0.0022 (6)0.0121 (10)
O20.067 (3)0.076 (3)0.0423 (18)0.004 (2)0.0038 (17)0.0078 (18)
C20.056 (4)0.060 (3)0.046 (3)0.013 (3)0.002 (3)0.005 (2)
Cl30.0411 (7)0.1031 (13)0.0776 (10)0.0110 (8)0.0036 (6)0.0147 (9)
C30.063 (4)0.075 (4)0.043 (3)0.018 (3)0.006 (3)0.005 (3)
O30.067 (3)0.129 (5)0.051 (2)0.005 (3)0.001 (2)0.028 (3)
Cl40.0770 (11)0.0890 (10)0.0803 (9)0.0171 (12)0.0051 (9)0.0206 (8)
O40.076 (3)0.071 (3)0.058 (2)0.013 (2)0.014 (2)0.014 (2)
C40.090 (4)0.044 (2)0.047 (3)0.004 (3)0.011 (3)0.002 (2)
C50.077 (4)0.050 (2)0.047 (3)0.004 (3)0.010 (3)0.008 (2)
C60.080 (5)0.102 (5)0.039 (3)0.028 (4)0.001 (3)0.003 (3)
C70.077 (5)0.110 (6)0.050 (3)0.006 (4)0.001 (3)0.036 (4)
C80.072 (5)0.096 (5)0.056 (3)0.019 (4)0.013 (3)0.003 (3)
C90.068 (4)0.055 (3)0.047 (3)0.005 (3)0.006 (3)0.002 (2)
C100.087 (5)0.054 (3)0.050 (3)0.013 (4)0.016 (3)0.001 (2)
C110.095 (5)0.076 (4)0.066 (4)0.001 (5)0.018 (4)0.011 (4)
C120.103 (6)0.092 (5)0.085 (5)0.007 (6)0.044 (5)0.032 (5)
C130.178 (11)0.086 (5)0.051 (4)0.022 (7)0.038 (5)0.022 (4)
C140.134 (8)0.112 (7)0.047 (4)0.007 (7)0.011 (4)0.018 (4)
C150.107 (6)0.085 (5)0.048 (3)0.003 (5)0.007 (3)0.011 (4)
C160.062 (4)0.051 (3)0.050 (3)0.007 (3)0.006 (3)0.008 (2)
C170.088 (6)0.107 (6)0.068 (4)0.004 (5)0.016 (4)0.038 (4)
Geometric parameters (Å, º) top
Au1—Cl22.2669 (15)C5—C61.535 (10)
Au1—Cl32.2732 (15)C5—H50.9800
Au1—Cl42.2766 (17)C6—C71.542 (12)
Au1—Cl12.2843 (16)C6—H6A0.9700
O1—C91.217 (9)C6—H6B0.9700
N1—C51.497 (7)C7—H7A0.9700
N1—C81.500 (8)C7—H7B0.9700
N1—C11.525 (8)C8—H8A0.9600
N1—H1A0.9100C8—H8B0.9600
C1—C21.523 (8)C8—H8C0.9600
C1—C71.541 (10)C9—C101.477 (7)
C1—H10.9800C10—C151.384 (11)
O2—C91.330 (9)C10—C111.389 (12)
O2—C31.433 (7)C11—C121.398 (10)
C2—C161.523 (9)C11—H110.9300
C2—C31.552 (9)C12—C131.354 (15)
C2—H20.9800C12—H120.9300
C3—C41.488 (10)C13—C141.333 (17)
C3—H30.9800C13—H130.9300
O3—C161.192 (9)C14—C151.399 (10)
O4—C161.314 (8)C14—H140.9300
O4—C171.478 (10)C15—H150.9300
C4—C51.521 (8)C17—H17A0.9600
C4—H4A0.9700C17—H17B0.9600
C4—H4B0.9700C17—H17C0.9600
Cl2—Au1—Cl3175.52 (8)C7—C6—H6A110.7
Cl2—Au1—Cl489.17 (7)C5—C6—H6B110.7
Cl3—Au1—Cl490.08 (7)C7—C6—H6B110.7
Cl2—Au1—Cl190.66 (7)H6A—C6—H6B108.8
Cl3—Au1—Cl190.37 (7)C1—C7—C6105.1 (6)
Cl4—Au1—Cl1176.33 (7)C1—C7—H7A110.7
C5—N1—C8112.8 (5)C6—C7—H7A110.7
C5—N1—C1101.7 (5)C1—C7—H7B110.7
C8—N1—C1114.5 (5)C6—C7—H7B110.7
C5—N1—H1A109.2H7A—C7—H7B108.8
C8—N1—H1A109.2N1—C8—H8A109.5
C1—N1—H1A109.2N1—C8—H8B109.5
C2—C1—N1108.7 (4)H8A—C8—H8B109.5
C2—C1—C7113.2 (6)N1—C8—H8C109.5
N1—C1—C7101.4 (5)H8A—C8—H8C109.5
C2—C1—H1111.1H8B—C8—H8C109.5
N1—C1—H1111.1O1—C9—O2123.1 (6)
C7—C1—H1111.1O1—C9—C10124.4 (7)
C9—O2—C3119.7 (5)O2—C9—C10112.5 (6)
C1—C2—C16111.7 (6)C15—C10—C11120.0 (6)
C1—C2—C3109.4 (5)C15—C10—C9121.1 (7)
C16—C2—C3110.7 (5)C11—C10—C9118.7 (7)
C1—C2—H2108.3C10—C11—C12118.0 (8)
C16—C2—H2108.3C10—C11—H11121.0
C3—C2—H2108.3C12—C11—H11121.0
O2—C3—C4107.9 (5)C13—C12—C11122.1 (9)
O2—C3—C2109.2 (5)C13—C12—H12118.9
C4—C3—C2111.7 (5)C11—C12—H12118.9
O2—C3—H3109.4C14—C13—C12119.2 (7)
C4—C3—H3109.4C14—C13—H13120.4
C2—C3—H3109.4C12—C13—H13120.4
C16—O4—C17115.2 (6)C13—C14—C15122.1 (10)
C3—C4—C5111.3 (5)C13—C14—H14119.0
C3—C4—H4A109.4C15—C14—H14119.0
C5—C4—H4A109.4C10—C15—C14118.6 (9)
C3—C4—H4B109.4C10—C15—H15120.7
C5—C4—H4B109.4C14—C15—H15120.7
H4A—C4—H4B108.0O3—C16—O4123.5 (6)
N1—C5—C4106.7 (4)O3—C16—C2123.7 (6)
N1—C5—C6102.2 (5)O4—C16—C2112.6 (6)
C4—C5—C6114.3 (6)O4—C17—H17A109.5
N1—C5—H5111.0O4—C17—H17B109.5
C4—C5—H5111.0H17A—C17—H17B109.5
C6—C5—H5111.0O4—C17—H17C109.5
C5—C6—C7105.1 (5)H17A—C17—H17C109.5
C5—C6—H6A110.7H17B—C17—H17C109.5
C5—N1—C1—C272.3 (5)C2—C1—C7—C687.9 (7)
C8—N1—C1—C2165.7 (5)N1—C1—C7—C628.4 (7)
C5—N1—C1—C747.1 (5)C5—C6—C7—C10.0 (8)
C8—N1—C1—C774.8 (6)C3—O2—C9—O19.1 (9)
N1—C1—C2—C1663.0 (6)C3—O2—C9—C10168.9 (5)
C7—C1—C2—C16174.8 (6)O1—C9—C10—C15168.4 (7)
N1—C1—C2—C359.8 (6)O2—C9—C10—C159.6 (9)
C7—C1—C2—C352.0 (7)O1—C9—C10—C116.7 (10)
C9—O2—C3—C4144.1 (6)O2—C9—C10—C11175.3 (6)
C9—O2—C3—C294.4 (6)C15—C10—C11—C121.6 (12)
C1—C2—C3—O2167.1 (6)C9—C10—C11—C12173.6 (7)
C16—C2—C3—O243.6 (7)C10—C11—C12—C130.9 (14)
C1—C2—C3—C447.9 (7)C11—C12—C13—C141.7 (18)
C16—C2—C3—C475.6 (6)C12—C13—C14—C150 (2)
O2—C3—C4—C5170.4 (5)C11—C10—C15—C143.1 (13)
C2—C3—C4—C550.5 (7)C9—C10—C15—C14171.9 (9)
C8—N1—C5—C4164.0 (6)C13—C14—C15—C102 (2)
C1—N1—C5—C472.9 (5)C17—O4—C16—O32.4 (11)
C8—N1—C5—C675.7 (7)C17—O4—C16—C2172.7 (6)
C1—N1—C5—C647.4 (6)C1—C2—C16—O337.0 (9)
C3—C4—C5—N164.8 (7)C3—C2—C16—O385.2 (9)
C3—C4—C5—C647.4 (7)C1—C2—C16—O4148.0 (5)
N1—C5—C6—C729.1 (7)C3—C2—C16—O489.9 (6)
C4—C5—C6—C785.8 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30.912.022.756 (6)136
C11—H11···O3i0.932.623.24 (1)125
C17—H17B···O3ii0.962.603.542 (9)168
C5—H5···Cl2iii0.982.903.633 (6)132
C4—H4B···Cl3iv0.972.803.750 (6)171
C6—H6A···Cl3v0.972.903.842 (7)165
C8—H8B···Cl40.962.853.703 (8)149
C2—H2···Cl4i0.982.783.759 (6)173
Symmetry codes: (i) x1, y, z; (ii) x1/2, y+1/2, z+2; (iii) x, y+1, z; (iv) x1, y+1, z; (v) x+3, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formula(C17H22NO4)[AuCl4]
Mr643.12
Crystal system, space groupOrthorhombic, P212121
Temperature (K)295
a, b, c (Å)7.7358 (3), 9.4543 (5), 29.9093 (13)
V3)2187.46 (17)
Z4
Radiation typeCu Kα
µ (mm1)17.33
Crystal size (mm)0.45 × 0.21 × 0.08
Data collection
DiffractometerBruker SMART CCD APEXII area-detector
diffractometer
Absorption correctionNumerical and multi-scan
[SHELXTL (Sheldrick, 2004) and SADABS (Bruker, 2005)]
Tmin, Tmax0.042, 0.338
No. of measured, independent and
observed [I > 2σ(I)] reflections
14526, 3906, 3804
Rint0.052
(sin θ/λ)max1)0.604
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.070, 1.05
No. of reflections3906
No. of parameters246
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.59, 0.96
Absolute structureFlack (1983), with 1468 Friedel pairs
Absolute structure parameter0.025 (14)

Computer programs: SMART (Bruker, 2006), SMART, SAINT-Plus (Bruker, 2005), SHELXS97 (Sheldrick, 2004), SHELXL97 (Sheldrick, 2004), SHELXTL (Sheldrick, 2004), SHELXTL.

Selected geometric parameters (Å, º) top
Au1—Cl22.2669 (15)Au1—Cl42.2766 (17)
Au1—Cl32.2732 (15)Au1—Cl12.2843 (16)
Cl2—Au1—Cl3175.52 (8)Cl2—Au1—Cl190.66 (7)
Cl2—Au1—Cl489.17 (7)Cl3—Au1—Cl190.37 (7)
Cl3—Au1—Cl490.08 (7)Cl4—Au1—Cl1176.33 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30.912.022.756 (6)136
C11—H11···O3i0.932.623.24 (1)125
C17—H17B···O3ii0.962.603.542 (9)168
C5—H5···Cl2iii0.982.903.633 (6)132
C4—H4B···Cl3iv0.972.803.750 (6)171
C6—H6A···Cl3v0.972.903.842 (7)165
C8—H8B···Cl40.962.853.703 (8)149
C2—H2···Cl4i0.982.783.759 (6)173
Symmetry codes: (i) x1, y, z; (ii) x1/2, y+1/2, z+2; (iii) x, y+1, z; (iv) x1, y+1, z; (v) x+3, y+1/2, z+3/2.
 

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