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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): m1098–m1099.
Published online 2010 August 18. doi:  10.1107/S1600536810031144
PMCID: PMC3008023

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

Abstract

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

An external file that holds a picture, illustration, etc.
Object name is e-66-m1098-scheme1.jpg

Experimental

Crystal data

  • [Au(C18H27ClN3)(C18H15P)](NO3)2
  • M r = 904.13
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1098-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.027
  • wR(F 2) = 0.059
  • S = 1.02
  • 10116 reflections
  • 535 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.79 e Å−3
  • Δρmin = −0.84 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031144/pv2313Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

[(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.

Refinement

Hydrogen atoms on carbon were included in calculated positions and were refined using a riding model at C–H = 0.95, 0.98 and 0.99 Å and Uiso(H) = 1.2, 1.5 and 1.2 × Ueq(C) of the aryl, methyl and methylene C-atoms, respectively. The hydrogen atom on N4 was refined semi-freely with the help of a distance restraint at N–H = 0.88 Å and Uiso(H) = 1.2 × Ueq(N). The presence of a residual electron density peak and the proximity of a nitrate anion indicated that N5 was protonated. Hydrogen atoms on N5 were included in calculated positions and were refined using a riding model at N–H = 0.93 Å and Uiso(H) = 1.2 × Ueq(N) .

Figures

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.

Crystal data

[Au(C18H27ClN3)(C18H15P)](NO3)2Z = 2
Mr = 904.13F(000) = 904
Triclinic, P1Dx = 1.638 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.2456 (5) ÅCell parameters from 9914 reflections
b = 13.1914 (6) Åθ = 2.6–28.2°
c = 13.6301 (7) ŵ = 4.18 mm1
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

Bruker APEXII CCD area-detector diffractometer10116 independent reflections
Radiation source: fine-focus sealed tube8781 reflections with I > 2σ(I)
graphiteRint = 0.030
[var phi] and ω scansθmax = 30.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −13→14
Tmin = 0.331, Tmax = 0.818k = −18→18
25641 measured reflectionsl = −18→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0268P)2 + 0.224P] where P = (Fo2 + 2Fc2)/3
10116 reflections(Δ/σ)max = 0.002
535 parametersΔρmax = 0.79 e Å3
1 restraintΔρmin = −0.84 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
Au0.665037 (10)0.182061 (8)0.594476 (7)0.02328 (4)
P0.82288 (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)
H5−0.21540.34510.22420.037*0.481 (4)
C1−0.3183 (7)0.4390 (6)0.0986 (5)0.0272 (14)0.481 (4)
H1A−0.33220.50340.13160.033*0.481 (4)
H1B−0.29420.45520.02860.033*0.481 (4)
C2−0.4399 (6)0.3793 (6)0.1079 (5)0.0415 (17)0.481 (4)
H2A−0.51350.42070.07910.062*0.481 (4)
H2B−0.45990.36150.17760.062*0.481 (4)
H2C−0.42510.31690.07320.062*0.481 (4)
C3−0.1635 (9)0.2834 (7)0.1254 (7)0.0293 (18)0.481 (4)
H3A−0.25040.25520.12160.035*0.481 (4)
H3B−0.12390.24530.18340.035*0.481 (4)
C4−0.0910 (9)0.2302 (8)0.0440 (7)0.058 (2)0.481 (4)
H4A−0.09450.15640.05700.087*0.481 (4)
H4B0.00040.24840.04090.087*0.481 (4)
H4C−0.13180.2512−0.01890.087*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'−0.23750.39870.21680.037*0.519 (4)
C1'−0.3049 (9)0.3885 (8)0.0918 (8)0.064 (3)0.519 (4)
H1'A−0.35270.32560.10360.076*0.519 (4)
H1'B−0.27770.39810.02160.076*0.519 (4)
C2'−0.3838 (8)0.4842 (7)0.1296 (7)0.069 (2)0.519 (4)
H2'A−0.46910.49220.09870.104*0.519 (4)
H2'B−0.33500.54500.11260.104*0.519 (4)
H2'C−0.39650.47530.20120.104*0.519 (4)
C3'−0.1431 (14)0.2479 (8)0.1467 (8)0.059 (3)0.519 (4)
H3'A−0.05710.22900.17600.071*0.519 (4)
H3'B−0.20920.19900.16940.071*0.519 (4)
C4'−0.1367 (9)0.2780 (6)0.0156 (6)0.0492 (19)0.519 (4)
H4'A−0.13840.2152−0.01850.074*0.519 (4)
H4'B−0.05600.3117−0.00290.074*0.519 (4)
H4'C−0.21240.3236−0.00320.074*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)
N30.5210 (2)0.23408 (16)0.49707 (16)0.0218 (4)
N40.2893 (3)0.38262 (19)0.27767 (19)0.0354 (6)
H40.293 (3)0.362 (2)0.2210 (16)0.042*
C5−0.0876 (3)0.4451 (3)0.1452 (2)0.0432 (8)
H5A−0.04060.44190.08080.052*
H5B−0.13370.51310.14730.052*
C60.0088 (3)0.4291 (3)0.2274 (2)0.0407 (8)
H6A0.04400.35740.23210.049*
H6B−0.03610.44330.29080.049*
C70.1203 (3)0.4995 (2)0.2076 (2)0.0292 (6)
H7A0.16000.48800.14180.035*
H7B0.08400.57090.20590.035*
C80.2266 (3)0.4855 (2)0.2828 (2)0.0288 (6)
H8A0.18570.49160.34990.035*
C90.3271 (3)0.5659 (2)0.2646 (3)0.0411 (8)
H9A0.39880.55130.31030.062*
H9B0.28540.63330.27490.062*
H9C0.36180.56490.19680.062*
C100.3611 (2)0.3343 (2)0.3491 (2)0.0252 (5)
C110.3767 (2)0.3752 (2)0.43949 (19)0.0239 (5)
H11A0.33250.43810.45360.029*
C120.4565 (3)0.3237 (2)0.50772 (19)0.0244 (5)
H12A0.46660.35450.56770.029*
C130.5037 (2)0.18783 (19)0.41085 (18)0.0206 (5)
C140.5651 (2)0.09074 (19)0.39948 (19)0.0235 (5)
H14A0.61660.05780.45050.028*
C150.5501 (2)0.04404 (19)0.3141 (2)0.0243 (5)
Cl0.63057 (7)−0.07417 (5)0.29880 (5)0.03084 (15)
C160.4726 (3)0.0892 (2)0.2383 (2)0.0286 (6)
H16A0.46260.05540.18000.034*
C170.4113 (3)0.1831 (2)0.2497 (2)0.0294 (6)
H17A0.35800.21380.19870.035*
C180.4253 (2)0.2355 (2)0.33543 (19)0.0241 (5)
C190.9009 (3)0.00417 (19)0.64813 (19)0.0238 (5)
C200.8238 (3)−0.0623 (2)0.6048 (2)0.0294 (6)
H20A0.7337−0.04430.59550.035*
C210.8771 (3)−0.1545 (2)0.5750 (2)0.0354 (7)
H21A0.8240−0.19890.54440.042*
C221.0076 (3)−0.1817 (2)0.5899 (2)0.0356 (7)
H22A1.0434−0.24610.57200.043*
C231.0859 (3)−0.1158 (2)0.6308 (3)0.0428 (8)
H23A1.1761−0.13420.63970.051*
C241.0332 (3)−0.0222 (2)0.6590 (2)0.0352 (7)
H24A1.08790.02380.68580.042*
C250.9531 (3)0.20251 (19)0.71033 (19)0.0224 (5)
C260.9777 (3)0.2794 (2)0.6378 (2)0.0284 (6)
H26A0.91940.29360.58510.034*
C271.0875 (3)0.3353 (2)0.6425 (2)0.0363 (7)
H27A1.10580.38620.59190.044*
C281.1707 (3)0.3170 (2)0.7209 (2)0.0380 (7)
H28A1.24640.35480.72330.046*
C291.1439 (3)0.2440 (2)0.7953 (2)0.0348 (7)
H29A1.19950.23300.84990.042*
C301.0360 (3)0.1870 (2)0.7902 (2)0.0295 (6)
H30A1.01790.13670.84140.035*
C310.7642 (2)0.0799 (2)0.81795 (19)0.0246 (5)
C320.6619 (3)0.1374 (2)0.8616 (2)0.0294 (6)
H32A0.62270.19550.82630.035*
C330.6179 (3)0.1098 (3)0.9562 (2)0.0417 (8)
H33A0.54840.14900.98580.050*
C340.6748 (3)0.0252 (3)1.0080 (2)0.0452 (8)
H34A0.64560.00731.07350.054*
C350.7737 (3)−0.0329 (3)0.9646 (2)0.0466 (9)
H35A0.8114−0.09160.99990.056*
C360.8185 (3)−0.0065 (2)0.8699 (2)0.0350 (7)
H36A0.8864−0.04720.84030.042*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Au0.02601 (6)0.02376 (5)0.02042 (5)−0.00079 (4)−0.00528 (4)−0.00233 (4)
P0.0256 (3)0.0196 (3)0.0201 (3)0.0005 (3)−0.0027 (3)−0.0022 (2)
N10.017 (3)0.023 (4)0.038 (5)−0.010 (3)0.004 (3)−0.020 (3)
O10.039 (3)0.067 (5)0.049 (4)0.010 (3)−0.014 (3)−0.022 (3)
O20.075 (4)0.049 (3)0.035 (3)0.023 (3)−0.007 (3)0.004 (2)
O30.053 (3)0.047 (3)0.029 (3)0.011 (2)−0.013 (2)−0.004 (2)
N50.036 (3)0.033 (6)0.0265 (19)−0.015 (5)−0.0003 (17)−0.006 (5)
C10.026 (3)0.035 (4)0.021 (3)0.004 (3)−0.003 (2)−0.005 (3)
C20.028 (3)0.052 (4)0.046 (4)−0.013 (3)−0.008 (3)−0.005 (3)
C30.035 (4)0.027 (5)0.027 (4)−0.016 (3)0.002 (3)−0.001 (3)
C40.052 (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)
N20.0287 (12)0.0258 (12)0.0328 (13)−0.0032 (10)0.0054 (10)−0.0056 (10)
O40.0540 (14)0.0294 (11)0.0370 (12)−0.0050 (10)0.0130 (10)−0.0117 (9)
O50.0638 (15)0.0386 (12)0.0328 (12)0.0051 (11)−0.0117 (11)−0.0076 (10)
O60.0619 (16)0.0328 (12)0.0491 (15)0.0070 (11)−0.0092 (12)0.0009 (11)
N30.0228 (11)0.0217 (11)0.0211 (11)−0.0007 (8)−0.0012 (8)−0.0028 (8)
N40.0446 (15)0.0291 (13)0.0328 (14)0.0132 (11)−0.0171 (12)−0.0108 (11)
C50.0322 (16)0.067 (2)0.0310 (17)−0.0116 (15)−0.0027 (13)0.0044 (15)
C60.0334 (16)0.059 (2)0.0311 (16)−0.0192 (15)−0.0072 (13)0.0057 (15)
C70.0296 (14)0.0244 (14)0.0326 (15)0.0005 (11)−0.0038 (12)0.0040 (11)
C80.0270 (14)0.0220 (13)0.0377 (16)0.0044 (11)−0.0064 (12)−0.0065 (11)
C90.0358 (17)0.0388 (18)0.051 (2)−0.0078 (14)−0.0045 (15)−0.0112 (15)
C100.0225 (13)0.0260 (13)0.0276 (14)0.0022 (10)−0.0064 (11)−0.0060 (11)
C110.0236 (13)0.0218 (12)0.0271 (14)0.0013 (10)−0.0017 (10)−0.0079 (10)
C120.0272 (13)0.0250 (13)0.0220 (13)−0.0041 (10)−0.0009 (10)−0.0056 (10)
C130.0198 (12)0.0216 (12)0.0204 (12)−0.0013 (9)0.0002 (9)−0.0016 (10)
C140.0217 (12)0.0242 (13)0.0241 (13)0.0018 (10)−0.0008 (10)−0.0013 (10)
C150.0213 (12)0.0227 (13)0.0291 (14)0.0019 (10)0.0013 (10)−0.0061 (11)
Cl0.0286 (3)0.0248 (3)0.0391 (4)0.0053 (3)0.0004 (3)−0.0085 (3)
C160.0318 (14)0.0289 (14)0.0264 (14)0.0016 (11)−0.0039 (11)−0.0110 (11)
C170.0323 (14)0.0305 (15)0.0256 (14)0.0058 (12)−0.0100 (11)−0.0063 (11)
C180.0236 (13)0.0246 (13)0.0247 (13)0.0019 (10)−0.0053 (10)−0.0066 (10)
C190.0305 (14)0.0215 (12)0.0190 (12)−0.0017 (10)0.0046 (10)−0.0005 (10)
C200.0379 (16)0.0239 (13)0.0263 (14)−0.0007 (12)−0.0026 (12)−0.0020 (11)
C210.0530 (19)0.0236 (14)0.0304 (16)−0.0055 (13)0.0011 (14)−0.0058 (12)
C220.0485 (18)0.0225 (14)0.0348 (17)−0.0008 (13)0.0175 (14)−0.0048 (12)
C230.0317 (16)0.0336 (17)0.062 (2)−0.0004 (13)0.0200 (15)−0.0089 (15)
C240.0295 (15)0.0284 (15)0.0488 (19)−0.0063 (12)0.0112 (13)−0.0113 (13)
C250.0253 (13)0.0210 (12)0.0213 (13)0.0001 (10)−0.0001 (10)−0.0046 (10)
C260.0330 (15)0.0281 (14)0.0243 (14)−0.0010 (11)−0.0017 (11)−0.0039 (11)
C270.0391 (17)0.0326 (16)0.0377 (17)−0.0075 (13)0.0088 (14)−0.0051 (13)
C280.0296 (15)0.0389 (17)0.0482 (19)−0.0058 (13)0.0041 (14)−0.0204 (15)
C290.0290 (15)0.0386 (17)0.0389 (17)0.0035 (13)−0.0087 (13)−0.0187 (14)
C300.0359 (15)0.0286 (14)0.0243 (14)0.0030 (12)−0.0037 (12)−0.0069 (11)
C310.0235 (13)0.0289 (14)0.0219 (13)−0.0018 (10)−0.0021 (10)−0.0048 (11)
C320.0295 (14)0.0279 (14)0.0315 (15)−0.0012 (11)−0.0007 (12)−0.0068 (12)
C330.0378 (17)0.0485 (19)0.0396 (18)−0.0014 (15)0.0138 (14)−0.0165 (15)
C340.0420 (19)0.067 (2)0.0250 (16)−0.0028 (17)0.0085 (14)0.0003 (15)
C350.0392 (18)0.061 (2)0.0348 (18)0.0052 (16)0.0036 (14)0.0191 (16)
C360.0309 (15)0.0408 (17)0.0303 (16)0.0082 (13)0.0044 (12)0.0061 (13)

Geometric parameters (Å, °)

Au—N32.070 (2)C7—C81.513 (4)
Au—P2.2338 (7)C7—H7A0.9900
P—C251.809 (3)C7—H7B0.9900
P—C191.814 (3)C8—C91.526 (4)
P—C311.816 (3)C8—H8A1.0000
N1—O21.197 (12)C9—H9A0.9800
N1—O31.226 (12)C9—H9B0.9800
N1—O11.343 (11)C9—H9C0.9800
N5—C31.119 (17)C10—C111.398 (4)
N5—C51.628 (16)C10—C181.445 (3)
N5—C11.801 (18)C11—C121.373 (4)
N5—H50.9300C11—H11A0.9500
C1—C21.511 (10)C12—H12A0.9500
C1—H1A0.9900C13—C141.409 (3)
C1—H1B0.9900C13—C181.413 (3)
C2—H2A0.9800C14—C151.373 (4)
C2—H2B0.9800C14—H14A0.9500
C2—H2C0.9800C15—C161.400 (4)
C3—C41.507 (14)C15—Cl1.742 (3)
C3—H3A0.9900C16—C171.371 (4)
C3—H3B0.9900C16—H16A0.9500
C4—H4A0.9800C17—C181.415 (4)
C4—H4B0.9800C17—H17A0.9500
C4—H4C0.9800C19—C241.388 (4)
N1'—O3'1.105 (16)C19—C201.389 (4)
N1'—O1'1.201 (9)C20—C211.385 (4)
N1'—O2'1.251 (8)C20—H20A0.9500
N5'—C1'1.38 (2)C21—C221.381 (4)
N5'—C51.405 (17)C21—H21A0.9500
N5'—C3'1.959 (14)C22—C231.377 (4)
N5'—H5'0.9300C22—H22A0.9500
C1'—C2'1.567 (12)C23—C241.392 (4)
C1'—H1'A0.9900C23—H23A0.9500
C1'—H1'B0.9900C24—H24A0.9500
C2'—H2'A0.9800C25—C261.393 (4)
C2'—H2'B0.9800C25—C301.398 (4)
C2'—H2'C0.9800C26—C271.388 (4)
C3'—C4'1.803 (14)C26—H26A0.9500
C3'—H3'A0.9900C27—C281.386 (5)
C3'—H3'B0.9900C27—H27A0.9500
C4'—H4'A0.9800C28—C291.380 (5)
C4'—H4'B0.9800C28—H28A0.9500
C4'—H4'C0.9800C29—C301.380 (4)
N2—O61.238 (3)C29—H29A0.9500
N2—O51.241 (3)C30—H30A0.9500
N2—O41.264 (3)C31—C361.393 (4)
N3—C121.334 (3)C31—C321.399 (4)
N3—C131.384 (3)C32—C331.384 (4)
N4—C101.340 (3)C32—H32A0.9500
N4—C81.471 (3)C33—C341.385 (5)
N4—H40.839 (18)C33—H33A0.9500
C5—C61.513 (4)C34—C351.377 (5)
C5—H5A0.9900C34—H34A0.9500
C5—H5B0.9900C35—C361.383 (4)
C6—C71.521 (4)C35—H35A0.9500
C6—H6A0.9900C36—H36A0.9500
C6—H6B0.9900
N3—Au—P176.94 (6)N4—C8—C9110.7 (2)
C25—P—C19105.97 (12)C7—C8—C9111.3 (2)
C25—P—C31105.86 (12)N4—C8—H8A108.8
C19—P—C31104.78 (12)C7—C8—H8A108.8
C25—P—Au115.47 (9)C9—C8—H8A108.8
C19—P—Au110.06 (9)C8—C9—H9A109.5
C31—P—Au113.88 (9)C8—C9—H9B109.5
O2—N1—O3123.8 (7)H9A—C9—H9B109.5
O2—N1—O1119.5 (9)C8—C9—H9C109.5
O3—N1—O1116.3 (9)H9A—C9—H9C109.5
C3—N5—C5116.5 (15)H9B—C9—H9C109.5
C3—N5—C1118.2 (15)N4—C10—C11122.5 (2)
C5—N5—C192.3 (6)N4—C10—C18120.5 (2)
C3—N5—H5109.6C11—C10—C18116.9 (2)
C5—N5—H5109.6C12—C11—C10119.5 (2)
C1—N5—H5109.6C12—C11—H11A120.3
C2—C1—N5105.1 (7)C10—C11—H11A120.3
C2—C1—H1A110.7N3—C12—C11125.6 (2)
N5—C1—H1A110.7N3—C12—H12A117.2
C2—C1—H1B110.7C11—C12—H12A117.2
N5—C1—H1B110.7N3—C13—C14118.6 (2)
H1A—C1—H1B108.8N3—C13—C18121.4 (2)
N5—C3—C4147.4 (12)C14—C13—C18120.0 (2)
N5—C3—H3A99.9C15—C14—C13119.5 (2)
C4—C3—H3A99.9C15—C14—H14A120.3
N5—C3—H3B99.9C13—C14—H14A120.3
C4—C3—H3B99.9C14—C15—C16121.8 (2)
H3A—C3—H3B104.2C14—C15—Cl119.3 (2)
O3'—N1'—O1'128.3 (11)C16—C15—Cl118.9 (2)
O3'—N1'—O2'110.2 (11)C17—C16—C15118.8 (2)
O1'—N1'—O2'121.5 (7)C17—C16—H16A120.6
C1'—N5'—C5131.5 (12)C15—C16—H16A120.6
C1'—N5'—C3'95.6 (9)C16—C17—C18121.8 (3)
C5—N5'—C3'105.3 (10)C16—C17—H17A119.1
C1'—N5'—H5'107.3C18—C17—H17A119.1
C5—N5'—H5'107.3C13—C18—C17118.1 (2)
C3'—N5'—H5'107.3C13—C18—C10119.2 (2)
N5'—C1'—C2'95.8 (8)C17—C18—C10122.6 (2)
N5'—C1'—H1'A112.6C24—C19—C20118.9 (2)
C2'—C1'—H1'A112.6C24—C19—P122.4 (2)
N5'—C1'—H1'B112.6C20—C19—P118.6 (2)
C2'—C1'—H1'B112.6C21—C20—C19120.7 (3)
H1'A—C1'—H1'B110.1C21—C20—H20A119.7
C1'—C2'—H2'A109.5C19—C20—H20A119.7
C1'—C2'—H2'B109.5C22—C21—C20119.8 (3)
H2'A—C2'—H2'B109.5C22—C21—H21A120.1
C1'—C2'—H2'C109.5C20—C21—H21A120.1
H2'A—C2'—H2'C109.5C23—C22—C21120.2 (3)
H2'B—C2'—H2'C109.5C23—C22—H22A119.9
C4'—C3'—N5'84.7 (7)C21—C22—H22A119.9
C4'—C3'—H3'A114.5C22—C23—C24120.0 (3)
N5'—C3'—H3'A114.5C22—C23—H23A120.0
C4'—C3'—H3'B114.5C24—C23—H23A120.0
N5'—C3'—H3'B114.5C19—C24—C23120.3 (3)
H3'A—C3'—H3'B111.6C19—C24—H24A119.9
C3'—C4'—H4'A109.5C23—C24—H24A119.9
C3'—C4'—H4'B109.5C26—C25—C30119.0 (2)
H4'A—C4'—H4'B109.5C26—C25—P119.4 (2)
C3'—C4'—H4'C109.5C30—C25—P121.4 (2)
H4'A—C4'—H4'C109.5C27—C26—C25119.9 (3)
H4'B—C4'—H4'C109.5C27—C26—H26A120.1
O6—N2—O5121.2 (2)C25—C26—H26A120.1
O6—N2—O4118.8 (3)C28—C27—C26120.3 (3)
O5—N2—O4120.0 (2)C28—C27—H27A119.9
C12—N3—C13117.2 (2)C26—C27—H27A119.9
C12—N3—Au119.89 (17)C29—C28—C27120.2 (3)
C13—N3—Au121.94 (16)C29—C28—H28A119.9
C10—N4—C8124.3 (2)C27—C28—H28A119.9
C10—N4—H4120 (2)C30—C29—C28119.8 (3)
C8—N4—H4114 (2)C30—C29—H29A120.1
N5'—C5—C6118.1 (7)C28—C29—H29A120.1
C6—C5—N5109.3 (7)C29—C30—C25120.7 (3)
N5'—C5—H5A114.5C29—C30—H30A119.7
C6—C5—H5A109.8C25—C30—H30A119.7
N5—C5—H5A109.8C36—C31—C32119.2 (3)
N5'—C5—H5B95.0C36—C31—P121.4 (2)
C6—C5—H5B109.8C32—C31—P119.4 (2)
N5—C5—H5B109.8C33—C32—C31120.0 (3)
H5A—C5—H5B108.3C33—C32—H32A120.0
C5—C6—C7109.9 (3)C31—C32—H32A120.0
C5—C6—H6A109.7C32—C33—C34120.2 (3)
C7—C6—H6A109.7C32—C33—H33A119.9
C5—C6—H6B109.7C34—C33—H33A119.9
C7—C6—H6B109.7C35—C34—C33120.0 (3)
H6A—C6—H6B108.2C35—C34—H34A120.0
C8—C7—C6114.3 (2)C33—C34—H34A120.0
C8—C7—H7A108.7C34—C35—C36120.5 (3)
C6—C7—H7A108.7C34—C35—H35A119.8
C8—C7—H7B108.7C36—C35—H35A119.8
C6—C7—H7B108.7C35—C36—C31120.0 (3)
H7A—C7—H7B107.6C35—C36—H36A120.0
N4—C8—C7108.4 (2)C31—C36—H36A120.0
C3—N5—C1—C263.6 (16)N4—C10—C18—C13178.0 (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—C474 (3)C11—C10—C18—C17176.3 (3)
C5—N5'—C1'—C2'−85.5 (15)C25—P—C19—C2420.4 (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—C24145.9 (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—C2085.1 (2)
C3'—N5'—C5—C6−66.6 (11)Au—P—C19—C20−37.7 (2)
C1'—N5'—C5—N5−122 (6)C24—C19—C20—C211.5 (4)
C3'—N5'—C5—N5−10 (5)P—C19—C20—C21−175.1 (2)
C3—N5—C5—N5'146 (7)C19—C20—C21—C221.2 (4)
C1—N5—C5—N5'23 (5)C20—C21—C22—C23−2.6 (5)
C3—N5—C5—C6−85.2 (15)C21—C22—C23—C241.3 (5)
C1—N5—C5—C6151.6 (6)C20—C19—C24—C23−2.8 (4)
N5'—C5—C6—C7−175.9 (7)P—C19—C24—C23173.6 (2)
N5—C5—C6—C7170.8 (7)C22—C23—C24—C191.4 (5)
C5—C6—C7—C8−176.8 (3)C19—P—C25—C2698.4 (2)
C10—N4—C8—C7−161.2 (3)C31—P—C25—C26−150.7 (2)
C10—N4—C8—C976.5 (4)Au—P—C25—C26−23.7 (2)
C6—C7—C8—N464.2 (3)C19—P—C25—C30−76.8 (2)
C6—C7—C8—C9−173.9 (3)C31—P—C25—C3034.1 (2)
C8—N4—C10—C114.3 (5)Au—P—C25—C30161.09 (19)
C8—N4—C10—C18−176.5 (3)C30—C25—C26—C273.7 (4)
N4—C10—C11—C12−177.1 (3)P—C25—C26—C27−171.6 (2)
C18—C10—C11—C123.6 (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—C11167.6 (2)C27—C28—C29—C301.9 (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—C1414.3 (3)P—C25—C30—C29172.5 (2)
C12—N3—C13—C182.6 (4)C25—P—C31—C36−89.6 (3)
Au—N3—C13—C18−166.36 (19)C19—P—C31—C3622.2 (3)
N3—C13—C14—C15−179.4 (2)Au—P—C31—C36142.5 (2)
C18—C13—C14—C151.2 (4)C25—P—C31—C3290.7 (2)
C13—C14—C15—C16−1.5 (4)C19—P—C31—C32−157.5 (2)
C13—C14—C15—Cl177.96 (19)Au—P—C31—C32−37.2 (2)
C14—C15—C16—C170.7 (4)C36—C31—C32—C331.5 (4)
Cl—C15—C16—C17−178.8 (2)P—C31—C32—C33−178.7 (2)
C15—C16—C17—C180.5 (4)C31—C32—C33—C340.0 (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—C361.1 (6)
N3—C13—C18—C10−0.4 (4)C34—C35—C36—C310.4 (5)
C14—C13—C18—C10178.9 (2)C32—C31—C36—C35−1.7 (5)
C16—C17—C18—C13−0.8 (4)P—C31—C36—C35178.5 (3)
C16—C17—C18—C10−179.8 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N5—H5···O40.931.772.70 (2)177
N5'—H5'···O40.932.002.81 (2)144
N4—H4···O2'0.84 (2)2.28 (2)3.030 (6)149 (3)
N4—H4···O3i0.84 (2)2.32 (3)3.013 (5)140 (3)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2313).

References

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