{4-[(7-Chloro-4-quinol­yl)amino]-N,N-di­ethyl­penta­naminium}(triphenyl­phos­phine)gold(I) dinitrate

Hitosugi-Levesque, M.; Tanski, J.M.

doi:10.1107/S1600536810031144

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages m1098-m1099

https://doi.org/10.1107/S1600536810031144

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{4-[(7-Chloro-4-quinolyl)amino]-N,N-diethylpentanaminium}(triphenylphosphine)gold(I) dinitrate

Marina Hitosugi-Levesque ^a and Joseph M. Tanski ^a ^*

^aDepartment of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA
^*Correspondence e-mail: jotanski@vassar.edu

(Received 27 July 2010; accepted 3 August 2010; online 18 August 2010)

The title compound, [Au(C₁₈H₂₇ClN₃)(C₁₈H₁₅P)](NO₃)₂, is a coordination complex of gold(I) triphenylphosphine with the N atom in the quinoline ring of the common antimalarial compound chloroquine (CQ). The pendant diethylamino group of the CQ ligand was found to be protonated. The complex exhibits a nearly linear coordination geometry around the Au^I atom [N—Au—P = 176.94 (6)°], with Au—N and Au—P bond lengths of 2.070 (2) and 2.2338 (7) Å, respectively. The diethylammonium group and one of the two nitrate counter-ions are disordered with occupancy ratios of 0.519 (4):0.481 (4). The nitrate anions are hydrogen bound to both the amino and ammonium groups of the N,N-diethylpentanaminium fragment of the CQ.

Related literature

For related structures, see: Karle & Karle (1988 ); Oleksyn & Serda (1993 ); Orlow et al. (2005 ); Borissova et al. (2008 ); Thwaite et al. (2004 ). For background to the metal coordination chemistry of chloroquine, see: Sánchez-Delgado et al. (1996 ); Navarro et al. (1997 , 2004 ). Widespread use of CQ has led to cross-resistance, limiting the efficacy of CQ-related treatments for malaria, see: World Health Organization (2010 ).

Experimental

Crystal data

[Au(C₁₈H₂₇ClN₃)(C₁₈H₁₅P)](NO₃)₂
M_r = 904.13
Triclinic, $[P \overline 1]$
a = 10.2456 (5) Å
b = 13.1914 (6) Å
c = 13.6301 (7) Å
α = 85.866 (1)°
β = 88.126 (1)°
γ = 86.510 (1)°
V = 1833.22 (15) Å³
Z = 2
Mo Kα radiation
μ = 4.18 mm⁻¹
T = 125 K
0.34 × 0.14 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.331, T_max = 0.818
25641 measured reflections
10116 independent reflections
8781 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.059
S = 1.02
10116 reflections
535 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.84 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯O4	0.93	1.77	2.70 (2)	177
N5′—H5′⋯O4	0.93	2.00	2.81 (2)	144
N4—H4⋯O2′	0.84 (2)	2.28 (2)	3.030 (6)	149 (3)
N4—H4⋯O3ⁱ	0.84 (2)	2.32 (3)	3.013 (5)	140 (3)
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810031144/pv2313sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810031144/pv2313Isup2.hkl

checkCIF report

Comment top

Chloroquine (CQ) has been used in treatments against the malaria parasites Plasmodium falciparum and Plasmodium vivax. Wide use of CQ has led to cross-resistance, limiting the efficacy of CQ related treatments. (World Health Organization, 2010). Complexing CQ with metal containing fragments such as gold(I) triphenylphosphine and gold (III) tetrachloride can enhance its ability to combat CQ-resistant strains of malaria (Navarro et al. 1997; Navarro et al. 2004), as can CQ complexes of Rh and Ru (Sánchez-Delgado et al. 1996). While some of the biological effects of coordinating metals to chloroquine and ts derivatives have been reported, a lack of structure-activity correlation remains.

In the title complex (Fig. 1) gold(I) is coordinated to the nitrogen atom in the quinoline ring as proposed earlier (Navarro et al. 1997). The complex exhibits a nearly linear coordination geometry around gold, with an N—Au—P angle of 176.94 (6)°. The Au—N and Au—P bond distance are 2.070 (2) Å and 2.2338 (7) Å, respectively. These bond distances are similar to those found in thre structure of (triphenylphosphine)gold(I) chloride, with Au—P 2.2313 (4) Å (Borissova et al., 2008), as well as the Au—N and Au—P distances in the structure of the cationic pyridine adduct (triphenylphosphine)gold(I) pyridine tetrafluoroborate, with Au—N 2.073 (3) Å and Au—P 2.2364 (8) Å (Thwaite et al., 2004). The pendant diethylamino group (N4) of the CQ ligand in the title complex was found to be protonated, and the nitrate anions are hydrogen bound to both the N1 amino and N4 ammonium groups of the 1,4-pentanediamine fragment of the CQ.

Related literature top

For related structures, see: Karle & Karle (1988); Oleksyn & Serda (1993); Orlow et al. (2005); Borissova et al. (2008); Thwaite et al. (2004). For background to the metal coordination chemistry of chloroquine, see: Sánchez-Delgado et al. (1996); Navarro et al. (1997, 2004). Widespread use of CQ has led to cross-resistance, limiting the efficacy of CQ-related treatments for malaria, see: World Health Organization (2010).

Experimental top

[(CQ)Au(PPh₃)][NO₃] was prepared from chloroquine (CQ) free base and triphenylphosphine (PPh₃) according to literature procedure (Navarro et al., 2004). The protonated title complex, [C₃₆H₄₂AuClPN₃](NO₃)₂ was obtained by diffusion of diethyl ether into an acetone solution of [(CQ)Au(PPh₃)][NO₃] over a period of two weeks. All manipulations were carried out under nitrogen using common Schlenck technique. X-ray diffraction quality crystals were separated as colorless plates.

Structure description top

For related structures, see: Karle & Karle (1988); Oleksyn & Serda (1993); Orlow et al. (2005); Borissova et al. (2008); Thwaite et al. (2004). For background to the metal coordination chemistry of chloroquine, see: Sánchez-Delgado et al. (1996); Navarro et al. (1997, 2004). Widespread use of CQ has led to cross-resistance, limiting the efficacy of CQ-related treatments for malaria, see: World Health Organization (2010).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of the title complex, with displacement ellipsoids shown at the 50% probability level. H atoms on carbon have been omitted for clarity; primed atoms represent the disordered fraction of the NO₃ ion and the diethylammonium group.

{4-[(7-Chloro-4-quinolyl)amino]-N,N- diethylpentanaminium}(triphenylphosphine)gold(I) dinitrate top

Crystal data top

[Au(C₁₈H₂₇ClN₃)(C₁₈H₁₅P)](NO₃)₂	Z = 2
M_r = 904.13	F(000) = 904
Triclinic, P1	D_x = 1.638 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2456 (5) Å	Cell parameters from 9914 reflections
b = 13.1914 (6) Å	θ = 2.6–28.2°
c = 13.6301 (7) Å	µ = 4.18 mm⁻¹
α = 85.866 (1)°	T = 125 K
β = 88.126 (1)°	Plate, colourless
γ = 86.510 (1)°	0.34 × 0.14 × 0.05 mm
V = 1833.22 (15) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	10116 independent reflections
Radiation source: fine-focus sealed tube	8781 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
φ and ω scans	θ_max = 30.4°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −13→14
T_min = 0.331, T_max = 0.818	k = −18→18
25641 measured reflections	l = −18→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.059	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0268P)² + 0.224P] where P = (F_o² + 2F_c²)/3
10116 reflections	(Δ/σ)_max = 0.002
535 parameters	Δρ_max = 0.79 e Å⁻³
1 restraint	Δρ_min = −0.84 e Å⁻³

Crystal data top

[Au(C₁₈H₂₇ClN₃)(C₁₈H₁₅P)](NO₃)₂	γ = 86.510 (1)°
M_r = 904.13	V = 1833.22 (15) Å³
Triclinic, P1	Z = 2
a = 10.2456 (5) Å	Mo Kα radiation
b = 13.1914 (6) Å	µ = 4.18 mm⁻¹
c = 13.6301 (7) Å	T = 125 K
α = 85.866 (1)°	0.34 × 0.14 × 0.05 mm
β = 88.126 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	10116 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	8781 reflections with I > 2σ(I)
T_min = 0.331, T_max = 0.818	R_int = 0.030
25641 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	1 restraint
wR(F²) = 0.059	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.79 e Å⁻³
10116 reflections	Δρ_min = −0.84 e Å⁻³
535 parameters

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Au	0.665037 (10)	0.182061 (8)	0.594476 (7)	0.02328 (4)
P	0.82288 (7)	0.11891 (5)	0.69465 (5)	0.02176 (13)
N1	−0.7853 (8)	0.3049 (6)	0.0355 (8)	0.0249 (19)	0.481 (4)
O1	−0.6757 (6)	0.2555 (6)	0.0027 (5)	0.0508 (16)	0.481 (4)
O2	−0.8285 (6)	0.3795 (4)	−0.0104 (4)	0.0542 (16)	0.481 (4)
O3	−0.8277 (5)	0.2750 (4)	0.1169 (4)	0.0433 (13)	0.481 (4)
N5	−0.1929 (19)	0.3572 (7)	0.1579 (14)	0.0312 (18)	0.481 (4)
H5	−0.2154	0.3451	0.2242	0.037*	0.481 (4)
C1	−0.3183 (7)	0.4390 (6)	0.0986 (5)	0.0272 (14)	0.481 (4)
H1A	−0.3322	0.5034	0.1316	0.033*	0.481 (4)
H1B	−0.2942	0.4552	0.0286	0.033*	0.481 (4)
C2	−0.4399 (6)	0.3793 (6)	0.1079 (5)	0.0415 (17)	0.481 (4)
H2A	−0.5135	0.4207	0.0791	0.062*	0.481 (4)
H2B	−0.4599	0.3615	0.1776	0.062*	0.481 (4)
H2C	−0.4251	0.3169	0.0732	0.062*	0.481 (4)
C3	−0.1635 (9)	0.2834 (7)	0.1254 (7)	0.0293 (18)	0.481 (4)
H3A	−0.2504	0.2552	0.1216	0.035*	0.481 (4)
H3B	−0.1239	0.2453	0.1834	0.035*	0.481 (4)
C4	−0.0910 (9)	0.2302 (8)	0.0440 (7)	0.058 (2)	0.481 (4)
H4A	−0.0945	0.1564	0.0570	0.087*	0.481 (4)
H4B	0.0004	0.2484	0.0409	0.087*	0.481 (4)
H4C	−0.1318	0.2512	−0.0189	0.087*	0.481 (4)
N1'	0.3290 (7)	0.3177 (6)	0.0098 (5)	0.0373 (13)	0.519 (4)
O1'	0.3781 (6)	0.2933 (5)	−0.0668 (5)	0.0708 (18)	0.519 (4)
O2'	0.3890 (6)	0.3670 (4)	0.0672 (3)	0.0610 (16)	0.519 (4)
O3'	0.2288 (17)	0.3057 (12)	0.0391 (12)	0.113 (5)	0.519 (4)
N5'	−0.2021 (18)	0.3913 (6)	0.1539 (13)	0.0312 (18)	0.519 (4)
H5'	−0.2375	0.3987	0.2168	0.037*	0.519 (4)
C1'	−0.3049 (9)	0.3885 (8)	0.0918 (8)	0.064 (3)	0.519 (4)
H1'A	−0.3527	0.3256	0.1036	0.076*	0.519 (4)
H1'B	−0.2777	0.3981	0.0216	0.076*	0.519 (4)
C2'	−0.3838 (8)	0.4842 (7)	0.1296 (7)	0.069 (2)	0.519 (4)
H2'A	−0.4691	0.4922	0.0987	0.104*	0.519 (4)
H2'B	−0.3350	0.5450	0.1126	0.104*	0.519 (4)
H2'C	−0.3965	0.4753	0.2012	0.104*	0.519 (4)
C3'	−0.1431 (14)	0.2479 (8)	0.1467 (8)	0.059 (3)	0.519 (4)
H3'A	−0.0571	0.2290	0.1760	0.071*	0.519 (4)
H3'B	−0.2092	0.1990	0.1694	0.071*	0.519 (4)
C4'	−0.1367 (9)	0.2780 (6)	0.0156 (6)	0.0492 (19)	0.519 (4)
H4'A	−0.1384	0.2152	−0.0185	0.074*	0.519 (4)
H4'B	−0.0560	0.3117	−0.0029	0.074*	0.519 (4)
H4'C	−0.2124	0.3236	−0.0032	0.074*	0.519 (4)
N2	−0.2745 (2)	0.40668 (18)	0.39973 (18)	0.0290 (5)
O4	−0.2598 (2)	0.32863 (15)	0.35104 (16)	0.0399 (5)
O5	−0.2412 (2)	0.40230 (17)	0.48672 (16)	0.0449 (6)
O6	−0.3220 (2)	0.48678 (17)	0.35888 (18)	0.0484 (6)
N3	0.5210 (2)	0.23408 (16)	0.49707 (16)	0.0218 (4)
N4	0.2893 (3)	0.38262 (19)	0.27767 (19)	0.0354 (6)
H4	0.293 (3)	0.362 (2)	0.2210 (16)	0.042*
C5	−0.0876 (3)	0.4451 (3)	0.1452 (2)	0.0432 (8)
H5A	−0.0406	0.4419	0.0808	0.052*
H5B	−0.1337	0.5131	0.1473	0.052*
C6	0.0088 (3)	0.4291 (3)	0.2274 (2)	0.0407 (8)
H6A	0.0440	0.3574	0.2321	0.049*
H6B	−0.0361	0.4433	0.2908	0.049*
C7	0.1203 (3)	0.4995 (2)	0.2076 (2)	0.0292 (6)
H7A	0.1600	0.4880	0.1418	0.035*
H7B	0.0840	0.5709	0.2059	0.035*
C8	0.2266 (3)	0.4855 (2)	0.2828 (2)	0.0288 (6)
H8A	0.1857	0.4916	0.3499	0.035*
C9	0.3271 (3)	0.5659 (2)	0.2646 (3)	0.0411 (8)
H9A	0.3988	0.5513	0.3103	0.062*
H9B	0.2854	0.6333	0.2749	0.062*
H9C	0.3618	0.5649	0.1968	0.062*
C10	0.3611 (2)	0.3343 (2)	0.3491 (2)	0.0252 (5)
C11	0.3767 (2)	0.3752 (2)	0.43949 (19)	0.0239 (5)
H11A	0.3325	0.4381	0.4536	0.029*
C12	0.4565 (3)	0.3237 (2)	0.50772 (19)	0.0244 (5)
H12A	0.4666	0.3545	0.5677	0.029*
C13	0.5037 (2)	0.18783 (19)	0.41085 (18)	0.0206 (5)
C14	0.5651 (2)	0.09074 (19)	0.39948 (19)	0.0235 (5)
H14A	0.6166	0.0578	0.4505	0.028*
C15	0.5501 (2)	0.04404 (19)	0.3141 (2)	0.0243 (5)
Cl	0.63057 (7)	−0.07417 (5)	0.29880 (5)	0.03084 (15)
C16	0.4726 (3)	0.0892 (2)	0.2383 (2)	0.0286 (6)
H16A	0.4626	0.0554	0.1800	0.034*
C17	0.4113 (3)	0.1831 (2)	0.2497 (2)	0.0294 (6)
H17A	0.3580	0.2138	0.1987	0.035*
C18	0.4253 (2)	0.2355 (2)	0.33543 (19)	0.0241 (5)
C19	0.9009 (3)	0.00417 (19)	0.64813 (19)	0.0238 (5)
C20	0.8238 (3)	−0.0623 (2)	0.6048 (2)	0.0294 (6)
H20A	0.7337	−0.0443	0.5955	0.035*
C21	0.8771 (3)	−0.1545 (2)	0.5750 (2)	0.0354 (7)
H21A	0.8240	−0.1989	0.5444	0.042*
C22	1.0076 (3)	−0.1817 (2)	0.5899 (2)	0.0356 (7)
H22A	1.0434	−0.2461	0.5720	0.043*
C23	1.0859 (3)	−0.1158 (2)	0.6308 (3)	0.0428 (8)
H23A	1.1761	−0.1342	0.6397	0.051*
C24	1.0332 (3)	−0.0222 (2)	0.6590 (2)	0.0352 (7)
H24A	1.0879	0.0238	0.6858	0.042*
C25	0.9531 (3)	0.20251 (19)	0.71033 (19)	0.0224 (5)
C26	0.9777 (3)	0.2794 (2)	0.6378 (2)	0.0284 (6)
H26A	0.9194	0.2936	0.5851	0.034*
C27	1.0875 (3)	0.3353 (2)	0.6425 (2)	0.0363 (7)
H27A	1.1058	0.3862	0.5919	0.044*
C28	1.1707 (3)	0.3170 (2)	0.7209 (2)	0.0380 (7)
H28A	1.2464	0.3548	0.7233	0.046*
C29	1.1439 (3)	0.2440 (2)	0.7953 (2)	0.0348 (7)
H29A	1.1995	0.2330	0.8499	0.042*
C30	1.0360 (3)	0.1870 (2)	0.7902 (2)	0.0295 (6)
H30A	1.0179	0.1367	0.8414	0.035*
C31	0.7642 (2)	0.0799 (2)	0.81795 (19)	0.0246 (5)
C32	0.6619 (3)	0.1374 (2)	0.8616 (2)	0.0294 (6)
H32A	0.6227	0.1955	0.8263	0.035*
C33	0.6179 (3)	0.1098 (3)	0.9562 (2)	0.0417 (8)
H33A	0.5484	0.1490	0.9858	0.050*
C34	0.6748 (3)	0.0252 (3)	1.0080 (2)	0.0452 (8)
H34A	0.6456	0.0073	1.0735	0.054*
C35	0.7737 (3)	−0.0329 (3)	0.9646 (2)	0.0466 (9)
H35A	0.8114	−0.0916	0.9999	0.056*
C36	0.8185 (3)	−0.0065 (2)	0.8699 (2)	0.0350 (7)
H36A	0.8864	−0.0472	0.8403	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au	0.02601 (6)	0.02376 (5)	0.02042 (5)	−0.00079 (4)	−0.00528 (4)	−0.00233 (4)
P	0.0256 (3)	0.0196 (3)	0.0201 (3)	0.0005 (3)	−0.0027 (3)	−0.0022 (2)
N1	0.017 (3)	0.023 (4)	0.038 (5)	−0.010 (3)	0.004 (3)	−0.020 (3)
O1	0.039 (3)	0.067 (5)	0.049 (4)	0.010 (3)	−0.014 (3)	−0.022 (3)
O2	0.075 (4)	0.049 (3)	0.035 (3)	0.023 (3)	−0.007 (3)	0.004 (2)
O3	0.053 (3)	0.047 (3)	0.029 (3)	0.011 (2)	−0.013 (2)	−0.004 (2)
N5	0.036 (3)	0.033 (6)	0.0265 (19)	−0.015 (5)	−0.0003 (17)	−0.006 (5)
C1	0.026 (3)	0.035 (4)	0.021 (3)	0.004 (3)	−0.003 (2)	−0.005 (3)
C2	0.028 (3)	0.052 (4)	0.046 (4)	−0.013 (3)	−0.008 (3)	−0.005 (3)
C3	0.035 (4)	0.027 (5)	0.027 (4)	−0.016 (3)	0.002 (3)	−0.001 (3)
C4	0.052 (6)	0.066 (7)	0.057 (6)	−0.005 (5)	0.003 (4)	−0.012 (5)
N1'	0.041 (4)	0.040 (3)	0.030 (3)	−0.001 (3)	−0.009 (3)	0.000 (3)
O1'	0.065 (4)	0.102 (5)	0.047 (3)	0.013 (3)	−0.012 (3)	−0.031 (3)
O2'	0.085 (4)	0.068 (4)	0.033 (3)	−0.022 (3)	−0.013 (3)	−0.004 (2)
O3'	0.128 (12)	0.129 (11)	0.080 (10)	0.012 (9)	−0.019 (8)	0.005 (8)
N5'	0.036 (3)	0.033 (6)	0.0265 (19)	−0.015 (5)	−0.0003 (17)	−0.006 (5)
C1'	0.046 (5)	0.065 (6)	0.084 (7)	0.005 (5)	−0.008 (4)	−0.035 (6)
C2'	0.048 (5)	0.095 (7)	0.064 (6)	0.005 (5)	−0.013 (4)	−0.004 (5)
C3'	0.107 (8)	0.036 (6)	0.034 (6)	−0.009 (5)	0.008 (5)	−0.003 (4)
C4'	0.063 (5)	0.045 (5)	0.041 (4)	−0.003 (4)	0.006 (4)	−0.019 (4)
N2	0.0287 (12)	0.0258 (12)	0.0328 (13)	−0.0032 (10)	0.0054 (10)	−0.0056 (10)
O4	0.0540 (14)	0.0294 (11)	0.0370 (12)	−0.0050 (10)	0.0130 (10)	−0.0117 (9)
O5	0.0638 (15)	0.0386 (12)	0.0328 (12)	0.0051 (11)	−0.0117 (11)	−0.0076 (10)
O6	0.0619 (16)	0.0328 (12)	0.0491 (15)	0.0070 (11)	−0.0092 (12)	0.0009 (11)
N3	0.0228 (11)	0.0217 (11)	0.0211 (11)	−0.0007 (8)	−0.0012 (8)	−0.0028 (8)
N4	0.0446 (15)	0.0291 (13)	0.0328 (14)	0.0132 (11)	−0.0171 (12)	−0.0108 (11)
C5	0.0322 (16)	0.067 (2)	0.0310 (17)	−0.0116 (15)	−0.0027 (13)	0.0044 (15)
C6	0.0334 (16)	0.059 (2)	0.0311 (16)	−0.0192 (15)	−0.0072 (13)	0.0057 (15)
C7	0.0296 (14)	0.0244 (14)	0.0326 (15)	0.0005 (11)	−0.0038 (12)	0.0040 (11)
C8	0.0270 (14)	0.0220 (13)	0.0377 (16)	0.0044 (11)	−0.0064 (12)	−0.0065 (11)
C9	0.0358 (17)	0.0388 (18)	0.051 (2)	−0.0078 (14)	−0.0045 (15)	−0.0112 (15)
C10	0.0225 (13)	0.0260 (13)	0.0276 (14)	0.0022 (10)	−0.0064 (11)	−0.0060 (11)
C11	0.0236 (13)	0.0218 (12)	0.0271 (14)	0.0013 (10)	−0.0017 (10)	−0.0079 (10)
C12	0.0272 (13)	0.0250 (13)	0.0220 (13)	−0.0041 (10)	−0.0009 (10)	−0.0056 (10)
C13	0.0198 (12)	0.0216 (12)	0.0204 (12)	−0.0013 (9)	0.0002 (9)	−0.0016 (10)
C14	0.0217 (12)	0.0242 (13)	0.0241 (13)	0.0018 (10)	−0.0008 (10)	−0.0013 (10)
C15	0.0213 (12)	0.0227 (13)	0.0291 (14)	0.0019 (10)	0.0013 (10)	−0.0061 (11)
Cl	0.0286 (3)	0.0248 (3)	0.0391 (4)	0.0053 (3)	0.0004 (3)	−0.0085 (3)
C16	0.0318 (14)	0.0289 (14)	0.0264 (14)	0.0016 (11)	−0.0039 (11)	−0.0110 (11)
C17	0.0323 (14)	0.0305 (15)	0.0256 (14)	0.0058 (12)	−0.0100 (11)	−0.0063 (11)
C18	0.0236 (13)	0.0246 (13)	0.0247 (13)	0.0019 (10)	−0.0053 (10)	−0.0066 (10)
C19	0.0305 (14)	0.0215 (12)	0.0190 (12)	−0.0017 (10)	0.0046 (10)	−0.0005 (10)
C20	0.0379 (16)	0.0239 (13)	0.0263 (14)	−0.0007 (12)	−0.0026 (12)	−0.0020 (11)
C21	0.0530 (19)	0.0236 (14)	0.0304 (16)	−0.0055 (13)	0.0011 (14)	−0.0058 (12)
C22	0.0485 (18)	0.0225 (14)	0.0348 (17)	−0.0008 (13)	0.0175 (14)	−0.0048 (12)
C23	0.0317 (16)	0.0336 (17)	0.062 (2)	−0.0004 (13)	0.0200 (15)	−0.0089 (15)
C24	0.0295 (15)	0.0284 (15)	0.0488 (19)	−0.0063 (12)	0.0112 (13)	−0.0113 (13)
C25	0.0253 (13)	0.0210 (12)	0.0213 (13)	0.0001 (10)	−0.0001 (10)	−0.0046 (10)
C26	0.0330 (15)	0.0281 (14)	0.0243 (14)	−0.0010 (11)	−0.0017 (11)	−0.0039 (11)
C27	0.0391 (17)	0.0326 (16)	0.0377 (17)	−0.0075 (13)	0.0088 (14)	−0.0051 (13)
C28	0.0296 (15)	0.0389 (17)	0.0482 (19)	−0.0058 (13)	0.0041 (14)	−0.0204 (15)
C29	0.0290 (15)	0.0386 (17)	0.0389 (17)	0.0035 (13)	−0.0087 (13)	−0.0187 (14)
C30	0.0359 (15)	0.0286 (14)	0.0243 (14)	0.0030 (12)	−0.0037 (12)	−0.0069 (11)
C31	0.0235 (13)	0.0289 (14)	0.0219 (13)	−0.0018 (10)	−0.0021 (10)	−0.0048 (11)
C32	0.0295 (14)	0.0279 (14)	0.0315 (15)	−0.0012 (11)	−0.0007 (12)	−0.0068 (12)
C33	0.0378 (17)	0.0485 (19)	0.0396 (18)	−0.0014 (15)	0.0138 (14)	−0.0165 (15)
C34	0.0420 (19)	0.067 (2)	0.0250 (16)	−0.0028 (17)	0.0085 (14)	0.0003 (15)
C35	0.0392 (18)	0.061 (2)	0.0348 (18)	0.0052 (16)	0.0036 (14)	0.0191 (16)
C36	0.0309 (15)	0.0408 (17)	0.0303 (16)	0.0082 (13)	0.0044 (12)	0.0061 (13)

Geometric parameters (Å, º) top

Au—N3	2.070 (2)	C7—C8	1.513 (4)
Au—P	2.2338 (7)	C7—H7A	0.9900
P—C25	1.809 (3)	C7—H7B	0.9900
P—C19	1.814 (3)	C8—C9	1.526 (4)
P—C31	1.816 (3)	C8—H8A	1.0000
N1—O2	1.197 (12)	C9—H9A	0.9800
N1—O3	1.226 (12)	C9—H9B	0.9800
N1—O1	1.343 (11)	C9—H9C	0.9800
N5—C3	1.119 (17)	C10—C11	1.398 (4)
N5—C5	1.628 (16)	C10—C18	1.445 (3)
N5—C1	1.801 (18)	C11—C12	1.373 (4)
N5—H5	0.9300	C11—H11A	0.9500
C1—C2	1.511 (10)	C12—H12A	0.9500
C1—H1A	0.9900	C13—C14	1.409 (3)
C1—H1B	0.9900	C13—C18	1.413 (3)
C2—H2A	0.9800	C14—C15	1.373 (4)
C2—H2B	0.9800	C14—H14A	0.9500
C2—H2C	0.9800	C15—C16	1.400 (4)
C3—C4	1.507 (14)	C15—Cl	1.742 (3)
C3—H3A	0.9900	C16—C17	1.371 (4)
C3—H3B	0.9900	C16—H16A	0.9500
C4—H4A	0.9800	C17—C18	1.415 (4)
C4—H4B	0.9800	C17—H17A	0.9500
C4—H4C	0.9800	C19—C24	1.388 (4)
N1'—O3'	1.105 (16)	C19—C20	1.389 (4)
N1'—O1'	1.201 (9)	C20—C21	1.385 (4)
N1'—O2'	1.251 (8)	C20—H20A	0.9500
N5'—C1'	1.38 (2)	C21—C22	1.381 (4)
N5'—C5	1.405 (17)	C21—H21A	0.9500
N5'—C3'	1.959 (14)	C22—C23	1.377 (4)
N5'—H5'	0.9300	C22—H22A	0.9500
C1'—C2'	1.567 (12)	C23—C24	1.392 (4)
C1'—H1'A	0.9900	C23—H23A	0.9500
C1'—H1'B	0.9900	C24—H24A	0.9500
C2'—H2'A	0.9800	C25—C26	1.393 (4)
C2'—H2'B	0.9800	C25—C30	1.398 (4)
C2'—H2'C	0.9800	C26—C27	1.388 (4)
C3'—C4'	1.803 (14)	C26—H26A	0.9500
C3'—H3'A	0.9900	C27—C28	1.386 (5)
C3'—H3'B	0.9900	C27—H27A	0.9500
C4'—H4'A	0.9800	C28—C29	1.380 (5)
C4'—H4'B	0.9800	C28—H28A	0.9500
C4'—H4'C	0.9800	C29—C30	1.380 (4)
N2—O6	1.238 (3)	C29—H29A	0.9500
N2—O5	1.241 (3)	C30—H30A	0.9500
N2—O4	1.264 (3)	C31—C36	1.393 (4)
N3—C12	1.334 (3)	C31—C32	1.399 (4)
N3—C13	1.384 (3)	C32—C33	1.384 (4)
N4—C10	1.340 (3)	C32—H32A	0.9500
N4—C8	1.471 (3)	C33—C34	1.385 (5)
N4—H4	0.839 (18)	C33—H33A	0.9500
C5—C6	1.513 (4)	C34—C35	1.377 (5)
C5—H5A	0.9900	C34—H34A	0.9500
C5—H5B	0.9900	C35—C36	1.383 (4)
C6—C7	1.521 (4)	C35—H35A	0.9500
C6—H6A	0.9900	C36—H36A	0.9500
C6—H6B	0.9900

N3—Au—P	176.94 (6)	N4—C8—C9	110.7 (2)
C25—P—C19	105.97 (12)	C7—C8—C9	111.3 (2)
C25—P—C31	105.86 (12)	N4—C8—H8A	108.8
C19—P—C31	104.78 (12)	C7—C8—H8A	108.8
C25—P—Au	115.47 (9)	C9—C8—H8A	108.8
C19—P—Au	110.06 (9)	C8—C9—H9A	109.5
C31—P—Au	113.88 (9)	C8—C9—H9B	109.5
O2—N1—O3	123.8 (7)	H9A—C9—H9B	109.5
O2—N1—O1	119.5 (9)	C8—C9—H9C	109.5
O3—N1—O1	116.3 (9)	H9A—C9—H9C	109.5
C3—N5—C5	116.5 (15)	H9B—C9—H9C	109.5
C3—N5—C1	118.2 (15)	N4—C10—C11	122.5 (2)
C5—N5—C1	92.3 (6)	N4—C10—C18	120.5 (2)
C3—N5—H5	109.6	C11—C10—C18	116.9 (2)
C5—N5—H5	109.6	C12—C11—C10	119.5 (2)
C1—N5—H5	109.6	C12—C11—H11A	120.3
C2—C1—N5	105.1 (7)	C10—C11—H11A	120.3
C2—C1—H1A	110.7	N3—C12—C11	125.6 (2)
N5—C1—H1A	110.7	N3—C12—H12A	117.2
C2—C1—H1B	110.7	C11—C12—H12A	117.2
N5—C1—H1B	110.7	N3—C13—C14	118.6 (2)
H1A—C1—H1B	108.8	N3—C13—C18	121.4 (2)
N5—C3—C4	147.4 (12)	C14—C13—C18	120.0 (2)
N5—C3—H3A	99.9	C15—C14—C13	119.5 (2)
C4—C3—H3A	99.9	C15—C14—H14A	120.3
N5—C3—H3B	99.9	C13—C14—H14A	120.3
C4—C3—H3B	99.9	C14—C15—C16	121.8 (2)
H3A—C3—H3B	104.2	C14—C15—Cl	119.3 (2)
O3'—N1'—O1'	128.3 (11)	C16—C15—Cl	118.9 (2)
O3'—N1'—O2'	110.2 (11)	C17—C16—C15	118.8 (2)
O1'—N1'—O2'	121.5 (7)	C17—C16—H16A	120.6
C1'—N5'—C5	131.5 (12)	C15—C16—H16A	120.6
C1'—N5'—C3'	95.6 (9)	C16—C17—C18	121.8 (3)
C5—N5'—C3'	105.3 (10)	C16—C17—H17A	119.1
C1'—N5'—H5'	107.3	C18—C17—H17A	119.1
C5—N5'—H5'	107.3	C13—C18—C17	118.1 (2)
C3'—N5'—H5'	107.3	C13—C18—C10	119.2 (2)
N5'—C1'—C2'	95.8 (8)	C17—C18—C10	122.6 (2)
N5'—C1'—H1'A	112.6	C24—C19—C20	118.9 (2)
C2'—C1'—H1'A	112.6	C24—C19—P	122.4 (2)
N5'—C1'—H1'B	112.6	C20—C19—P	118.6 (2)
C2'—C1'—H1'B	112.6	C21—C20—C19	120.7 (3)
H1'A—C1'—H1'B	110.1	C21—C20—H20A	119.7
C1'—C2'—H2'A	109.5	C19—C20—H20A	119.7
C1'—C2'—H2'B	109.5	C22—C21—C20	119.8 (3)
H2'A—C2'—H2'B	109.5	C22—C21—H21A	120.1
C1'—C2'—H2'C	109.5	C20—C21—H21A	120.1
H2'A—C2'—H2'C	109.5	C23—C22—C21	120.2 (3)
H2'B—C2'—H2'C	109.5	C23—C22—H22A	119.9
C4'—C3'—N5'	84.7 (7)	C21—C22—H22A	119.9
C4'—C3'—H3'A	114.5	C22—C23—C24	120.0 (3)
N5'—C3'—H3'A	114.5	C22—C23—H23A	120.0
C4'—C3'—H3'B	114.5	C24—C23—H23A	120.0
N5'—C3'—H3'B	114.5	C19—C24—C23	120.3 (3)
H3'A—C3'—H3'B	111.6	C19—C24—H24A	119.9
C3'—C4'—H4'A	109.5	C23—C24—H24A	119.9
C3'—C4'—H4'B	109.5	C26—C25—C30	119.0 (2)
H4'A—C4'—H4'B	109.5	C26—C25—P	119.4 (2)
C3'—C4'—H4'C	109.5	C30—C25—P	121.4 (2)
H4'A—C4'—H4'C	109.5	C27—C26—C25	119.9 (3)
H4'B—C4'—H4'C	109.5	C27—C26—H26A	120.1
O6—N2—O5	121.2 (2)	C25—C26—H26A	120.1
O6—N2—O4	118.8 (3)	C28—C27—C26	120.3 (3)
O5—N2—O4	120.0 (2)	C28—C27—H27A	119.9
C12—N3—C13	117.2 (2)	C26—C27—H27A	119.9
C12—N3—Au	119.89 (17)	C29—C28—C27	120.2 (3)
C13—N3—Au	121.94 (16)	C29—C28—H28A	119.9
C10—N4—C8	124.3 (2)	C27—C28—H28A	119.9
C10—N4—H4	120 (2)	C30—C29—C28	119.8 (3)
C8—N4—H4	114 (2)	C30—C29—H29A	120.1
N5'—C5—C6	118.1 (7)	C28—C29—H29A	120.1
C6—C5—N5	109.3 (7)	C29—C30—C25	120.7 (3)
N5'—C5—H5A	114.5	C29—C30—H30A	119.7
C6—C5—H5A	109.8	C25—C30—H30A	119.7
N5—C5—H5A	109.8	C36—C31—C32	119.2 (3)
N5'—C5—H5B	95.0	C36—C31—P	121.4 (2)
C6—C5—H5B	109.8	C32—C31—P	119.4 (2)
N5—C5—H5B	109.8	C33—C32—C31	120.0 (3)
H5A—C5—H5B	108.3	C33—C32—H32A	120.0
C5—C6—C7	109.9 (3)	C31—C32—H32A	120.0
C5—C6—H6A	109.7	C32—C33—C34	120.2 (3)
C7—C6—H6A	109.7	C32—C33—H33A	119.9
C5—C6—H6B	109.7	C34—C33—H33A	119.9
C7—C6—H6B	109.7	C35—C34—C33	120.0 (3)
H6A—C6—H6B	108.2	C35—C34—H34A	120.0
C8—C7—C6	114.3 (2)	C33—C34—H34A	120.0
C8—C7—H7A	108.7	C34—C35—C36	120.5 (3)
C6—C7—H7A	108.7	C34—C35—H35A	119.8
C8—C7—H7B	108.7	C36—C35—H35A	119.8
C6—C7—H7B	108.7	C35—C36—C31	120.0 (3)
H7A—C7—H7B	107.6	C35—C36—H36A	120.0
N4—C8—C7	108.4 (2)	C31—C36—H36A	120.0

C3—N5—C1—C2	63.6 (16)	N4—C10—C18—C13	178.0 (3)
C5—N5—C1—C2	−174.5 (7)	C11—C10—C18—C13	−2.7 (4)
C5—N5—C3—C4	−34 (3)	N4—C10—C18—C17	−3.0 (4)
C1—N5—C3—C4	74 (3)	C11—C10—C18—C17	176.3 (3)
C5—N5'—C1'—C2'	−85.5 (15)	C25—P—C19—C24	20.4 (3)
C3'—N5'—C1'—C2'	158.3 (8)	C31—P—C19—C24	−91.3 (2)
C1'—N5'—C3'—C4'	54.7 (10)	Au—P—C19—C24	145.9 (2)
C5—N5'—C3'—C4'	−81.1 (10)	C25—P—C19—C20	−163.2 (2)
C1'—N5'—C5—C6	−178.7 (11)	C31—P—C19—C20	85.1 (2)
C3'—N5'—C5—C6	−66.6 (11)	Au—P—C19—C20	−37.7 (2)
C1'—N5'—C5—N5	−122 (6)	C24—C19—C20—C21	1.5 (4)
C3'—N5'—C5—N5	−10 (5)	P—C19—C20—C21	−175.1 (2)
C3—N5—C5—N5'	146 (7)	C19—C20—C21—C22	1.2 (4)
C1—N5—C5—N5'	23 (5)	C20—C21—C22—C23	−2.6 (5)
C3—N5—C5—C6	−85.2 (15)	C21—C22—C23—C24	1.3 (5)
C1—N5—C5—C6	151.6 (6)	C20—C19—C24—C23	−2.8 (4)
N5'—C5—C6—C7	−175.9 (7)	P—C19—C24—C23	173.6 (2)
N5—C5—C6—C7	170.8 (7)	C22—C23—C24—C19	1.4 (5)
C5—C6—C7—C8	−176.8 (3)	C19—P—C25—C26	98.4 (2)
C10—N4—C8—C7	−161.2 (3)	C31—P—C25—C26	−150.7 (2)
C10—N4—C8—C9	76.5 (4)	Au—P—C25—C26	−23.7 (2)
C6—C7—C8—N4	64.2 (3)	C19—P—C25—C30	−76.8 (2)
C6—C7—C8—C9	−173.9 (3)	C31—P—C25—C30	34.1 (2)
C8—N4—C10—C11	4.3 (5)	Au—P—C25—C30	161.09 (19)
C8—N4—C10—C18	−176.5 (3)	C30—C25—C26—C27	3.7 (4)
N4—C10—C11—C12	−177.1 (3)	P—C25—C26—C27	−171.6 (2)
C18—C10—C11—C12	3.6 (4)	C25—C26—C27—C28	−2.0 (4)
C13—N3—C12—C11	−1.6 (4)	C26—C27—C28—C29	−0.9 (5)
Au—N3—C12—C11	167.6 (2)	C27—C28—C29—C30	1.9 (4)
C10—C11—C12—N3	−1.6 (4)	C28—C29—C30—C25	−0.2 (4)
C12—N3—C13—C14	−176.8 (2)	C26—C25—C30—C29	−2.7 (4)
Au—N3—C13—C14	14.3 (3)	P—C25—C30—C29	172.5 (2)
C12—N3—C13—C18	2.6 (4)	C25—P—C31—C36	−89.6 (3)
Au—N3—C13—C18	−166.36 (19)	C19—P—C31—C36	22.2 (3)
N3—C13—C14—C15	−179.4 (2)	Au—P—C31—C36	142.5 (2)
C18—C13—C14—C15	1.2 (4)	C25—P—C31—C32	90.7 (2)
C13—C14—C15—C16	−1.5 (4)	C19—P—C31—C32	−157.5 (2)
C13—C14—C15—Cl	177.96 (19)	Au—P—C31—C32	−37.2 (2)
C14—C15—C16—C17	0.7 (4)	C36—C31—C32—C33	1.5 (4)
Cl—C15—C16—C17	−178.8 (2)	P—C31—C32—C33	−178.7 (2)
C15—C16—C17—C18	0.5 (4)	C31—C32—C33—C34	0.0 (5)
N3—C13—C18—C17	−179.5 (2)	C32—C33—C34—C35	−1.3 (5)
C14—C13—C18—C17	−0.1 (4)	C33—C34—C35—C36	1.1 (6)
N3—C13—C18—C10	−0.4 (4)	C34—C35—C36—C31	0.4 (5)
C14—C13—C18—C10	178.9 (2)	C32—C31—C36—C35	−1.7 (5)
C16—C17—C18—C13	−0.8 (4)	P—C31—C36—C35	178.5 (3)
C16—C17—C18—C10	−179.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O4	0.93	1.77	2.70 (2)	177
N5′—H5′···O4	0.93	2.00	2.81 (2)	144
N4—H4···O2′	0.84 (2)	2.28 (2)	3.030 (6)	149 (3)
N4—H4···O3ⁱ	0.84 (2)	2.32 (3)	3.013 (5)	140 (3)

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[Au(C₁₈H₂₇ClN₃)(C₁₈H₁₅P)](NO₃)₂
M_r	904.13
Crystal system, space group	Triclinic, P1
Temperature (K)	125
a, b, c (Å)	10.2456 (5), 13.1914 (6), 13.6301 (7)
α, β, γ (°)	85.866 (1), 88.126 (1), 86.510 (1)
V (Å³)	1833.22 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.18
Crystal size (mm)	0.34 × 0.14 × 0.05

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.331, 0.818
No. of measured, independent and observed [I > 2σ(I)] reflections	25641, 10116, 8781
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.711

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.059, 1.02
No. of reflections	10116
No. of parameters	535
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.84

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O4	0.93	1.77	2.70 (2)	177
N5'—H5'···O4	0.93	2.00	2.81 (2)	144
N4—H4···O2'	0.84 (2)	2.28 (2)	3.030 (6)	149 (3)
N4—H4···O3ⁱ	0.84 (2)	2.32 (3)	3.013 (5)	140 (3)

Symmetry code: (i) x+1, y, z.

Acknowledgements

This work was supported by Vassar College. X-ray facilities were provided by the US National Science Foundation (grant No. 0521237 to JMT).

References

Borissova, A. O., Korlyukov, A. A., Antipin, M. Y. & Lyssenko, K. A. (2008). J. Phys. Chem. A, 112, 11519–11522. Web of Science CSD CrossRef PubMed CAS Google Scholar
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Volume 66| Part 9| September 2010| Pages m1098-m1099

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

{4-[(7-Chloro-4-quinol­yl)amino]-N,N-di­ethyl­penta­naminium}(tri­phenyl­phos­phine)gold(I) dinitrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{4-[(7-Chloro-4-quinolyl)amino]-N,N-diethylpentanaminium}(triphenylphosphine)gold(I) dinitrate