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In the title complex, [Au(C12H8N5O4)(C18H15P)], the coordination geometry about the AuI ion is linear, with one deprotonated 1,3-bis(4-nitro­phenyl)­triazenide ion, [O2NC6H4N=N-NC6H4NO2]-, acting as a monodentate ligand (two-electron donor), and one neutral tri­phenyl­phosphine mol­ecule completing the metal coordination. The triazenide ligand is almost planar (r.m.s. deviation = 0.0767 Å), with the largest interplanar angle being 11.6 (7)° between the phenyl ring of one of the terminal 4-nitro­phenyl substituents and the plane defined by the N=N-N triad. The Au-N and Au-P distances are 2.108 (5) and 2.2524 (13) Å, respectively. Pairs of mol­ecules generated by centrosymmetry are associated into a supramolecular array via intermolecular C-H...O inter­actions, and N...C and N...O [pi]-[pi] interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103018481/sq1026sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103018481/sq1026Isup2.hkl
Contains datablock I

CCDC reference: 224503

Comment top

Although metal complexes with 1,3-diaryl-substituted triazenide ligands, [ArNNNAr], have been extensively investigated in the past, only a few citations concerning mononuclear gold(I) complexes with monodentate triazenide ligands are found in the literature. More recently, monodentate diaryltriazenide complexes have received attention in connection with the fluxional behavior of such compounds, in which transition metal fragments MLn, such as AuPPh3, show N1—N3 σσ migration on the nitrogen chain (Peregudov et al., 1998, 2000). Beside the AuPPh3 group, to date only six monodentate diaryltriazenide complexes incorporating MLn fragments (where L is phosphine) have been characterized by single-crystal X-ray diffraction: cis-chlorobis(triphenylphosphine)(1,3-di-p-tolyltriazenido)palladium(II) and cis-chlorobis(triphenylphosphine)(1,3-di-p-tolyltriazenido)platinum(II) chloroform solvate (Bombieri et al., 1976), trans-hydridobis(triphenylphosphine)(1,3-di-p-tolyltriazenido)platinum(II) (Immirzi et al., 1976), cis-bis(triphenylphosphine)bis(1,3-diphenyltriazenido)platinum(II) benzene solvate (Brown et al., 1976), trans-carbonyl(1,3-di-p-tolyltriazenido)bis(triphenylphosphine)iridium(I) (Immirzi et al., 1980) and trans-[1,3-bis(4-fluorophenyl)-1-triazenato-N](2-methylphenyl)bis(triethyl- phosphine)nickel(II) (Peregudov et al., 2000).

Recently, the analogy between the isolobal species [(Ph3P)Au]+ and H+ was connected with the formal zwitterionic bond structure of the complex N-(triphenylphosphinegold)-N-(5-methoxyquinolyl-8)–2,4,6-trinitroaniline, compared with the structure of the free N-(5-methoxyquinolyl-8)–2,4,6-trinitroaniline obtained by ab initio quantum chemical calculation (Kuz'mina et al., 2001).

Based on the fact that [(Ph3P)Au]+ and H+ are isolobal particles, and on the potential of triazenes for sigmatropic migration of the H atom on the nitrogen triad, our goal was to investigate the title complex, (I), resulting from the substitution of H+ on the diazoamino group of 1,3-bis-(4-nitrophenyl)triazene by the [(Ph3P)Au]+ cation, and the results are presented here. \sch

The crystal structure of (I) reveals discrete asymmetric two-coordinate mononuclear AuI complexes. The deprotonated 1,3-bis(4-nitrophenyl)triazenide ion acts as an N1–η1 monodentate (two-electron donor) ligand, while one neutral triphenylphosphine molecule completes the coordination environment of the metal ion to an almost linear arrangement (Fig. 1).

Deviations from normal N—N and N—Caryl bond lengths in (I) (Table 1) give evidence for the delocalization of the π electrons on the N—NN group towards the terminal aryl substituents. The N2N3 bond [1.290 (7) Å] is longer than the typical value for a double bond (1.24 Å), while N1—N2 [1.324 (6) Å] is shorter than the characteristic value for a single bond (1.44 Å; International Tables for X-Ray Crystallography, 1985, Vol III, p. 270). Both N1—C1B [1.390 (8) Å] and N3—C1A [1.402 (7) Å] are shorter than expected for an N—Caryl single bond [1.452 Å for secondary amines, NHR2, with R = Csp2; Orpen et al., 1989]. These values are in good agreement with the distances found in the related compound trans-[1,3-bis(4-fluorophenyl)-1-triazenato-N](2-methylphenyl)bis(triethyl phosphine)nickel(II) [N1N2 1.298 (7) and N2—N3 1.326 (7) Å; Peregudov et al., 2000).

The Au—N1 bond distance of 2.108 (5) Å in (I) is close to the sum of the covalent radii (2.144 Å; Allen et al., 1987; Teatum et al., 1960) and corresponds to a covalent single bond. This value is longer than that observed in the related compound [Au(RN1N2—N3—N4N5R)(PPh3)], hereinafter (II) [where R is p-tolyl; Au—N3 2.082 (5) Å; Beck, 1988], suggesting that the 1,3-bis(4-nitrophenyl)triazenide ion possesses minor basicity compared with the 1,5-ditolyl-1,4-pentazadienide ion, [(tolN5tol)], as consequence of the π acidity of both terminal 4-nitrophenyl substituents. On the other hand, the Au—P bond distance of 2.2524 (13) Å in (I) is significantly shorter than the sum of the covalent radii (2.530 Å; Allen et al., 1987; Teatum et al., 1960) and is in good agreement with that found in (II) [Au1—P1 2.234 (3) Å].

The coordination angle of the AuI ion in (I) [N1—Au—P 178.70 (13)°] deviates only slightly from the ideal value of 180° and is very close to that found in (II) [N3—Au1—P1 178.35°]. Due to the delocalization of the π electrons over the nitro groups and the phenyl rings C1A—C6A and C1B—C6B towards the N1—N2N3 chain, the triazenide ligand is nearly planar, with interplanar angles as follows: between the plane of atoms O1A, N6 and O2A and the C1A—C6A ring 5(1)°, between the C1A—C6A ring and N1—N2N3 3.5 (7)°, between the C1B—C6B ring and N1—N2N3 11.6 (7)°, between the plane of atoms O1B, N5 and O2B and the C1B—C6B ring 3(1)°, and between the C1A—C6A and C1B—C6B rings 8.9 (4)°.

The crystal structure of (I) reveals pairs of molecules generated by centrosymmetry, which are associated into a supramolecular array via C—H···O intermolecular interactions (Table 2), and via N···C and N···O ππ interactions (Fig. 2), with N6···C6Bi 3.282 (8), N3···C6Bii 3.357 (8), O1B···N6iii 3.136 (9) and N5···O1Aiii 3.234 (9) Å [symmetry codes: (i) x, 1 + y, z; (ii) −x, 1 − y, −z; (iii) x − 1, 1 − y, −z]. These values are similar to those for ππ contacts found in free 1,3-bis(3-nitrophenyl)triazene (Zhang et al., 1999) [N···C 3.387 (3), and N···O 2.992 (2), 3.304 (3) and 3.023 (2) Å]. On the other hand, simultaneous weak intermolecular N6···C6Bi and N3···C6Bii contacts hinder the coplanarity of the C1B—C6B phenyl ring with the plane defined by the N1—N2N3 group [interplanar angle 11.6 (7)°]. All phenyl rings in (I) are planar to within experimental error (average r.m.s. deviation 0.0062 Å).

Experimental top

1,3-Bis(4-nitrophenyl)triazene (28.7 mg, 0.1 mmol) was dissolved in absolute tetrahydrofuran (20 ml) and treated with small portions of metallic sodium powder until H2 evolution stopped. The resulting intense-red mixture was filtered over a sintered-glass frit to eliminate the excess of metallic sodium. A solution of Ph3PAuCl (49.5 mg, 0.1 mmol) in absolute tetrahydrofuran was added slowly with continuous stirring. After stirring at room temperature for 1 h, the yellow precipitate of the complex was filtered off and dried in vacuo. Red prism-shaped crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation at room temperature of a solution of the complex in pyridine (yield: 41 mg, 55%; m.p. 506–507 K).

Refinement top

The positional parameters of the H atoms were obtained geometrically, with the C—H distances fixed (0.93 Å for Csp2), and H atoms were refined as riding on their respective C atoms, with Uiso(H) = 1.2Ueq(Csp2). The nitro O atoms show a large thermal motion, indicated by their elongated displacement ellipsoids (Fig. 1). Split peaks for these atoms were not observed and consequently a disorder model was not used in the refinement.

Computing details top

Data collection: COLLECT (Nonius BV, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability and H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The unit cell of (I) in a view slightly inclined towards [010]. The transmolecular N···O ππ interactions are shown as dashed lines [symmetry code: (iii) −x − 1, 1 − y, −z].
(I) top
Crystal data top
[Au(C12H8N5O4)(C18H15P)]Z = 2
Mr = 745.47F(000) = 728
Triclinic, P1Dx = 1.701 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.2034 (4) ÅCell parameters from 11145 reflections
b = 10.7550 (2) Åθ = 1.0–27.5°
c = 14.0941 (5) ŵ = 5.15 mm1
α = 93.987 (2)°T = 296 K
β = 102.148 (2)°Prism, red
γ = 103.930 (2)°0.30 × 0.20 × 0.10 mm
V = 1455.73 (8) Å3
Data collection top
Nonius KappaCCD area-detector
diffractometer
6639 independent reflections
Radiation source: fine-focus sealed tube5647 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromatorRint = 0.034
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 2.3°
CCD scansh = 1313
Absorption correction: analytical
(Alcock, 1970)
k = 1311
Tmin = 0.438, Tmax = 0.648l = 1817
15644 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047 w = 1/[σ2(Fo2) + (0.0698P)2 + 3.1565P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.133(Δ/σ)max < 0.001
S = 1.09Δρmax = 1.27 e Å3
6639 reflectionsΔρmin = 1.20 e Å3
370 parameters
Crystal data top
[Au(C12H8N5O4)(C18H15P)]γ = 103.930 (2)°
Mr = 745.47V = 1455.73 (8) Å3
Triclinic, P1Z = 2
a = 10.2034 (4) ÅMo Kα radiation
b = 10.7550 (2) ŵ = 5.15 mm1
c = 14.0941 (5) ÅT = 296 K
α = 93.987 (2)°0.30 × 0.20 × 0.10 mm
β = 102.148 (2)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
6639 independent reflections
Absorption correction: analytical
(Alcock, 1970)
5647 reflections with I > 2σ(I)
Tmin = 0.438, Tmax = 0.648Rint = 0.034
15644 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.09Δρmax = 1.27 e Å3
6639 reflectionsΔρmin = 1.20 e Å3
370 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.

Mean-plane data from final SHELXL refinement run:-

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 6.1857 (0.0721) x − 2.9505 (0.1357) y + 11.6709 (0.0375) z = 0.2513 (0.1783)

* 0.0000 (0.0001) O1A * 0.0000 (0.0001) N6 * 0.0000 (0.0000) O2A

Rms deviation of fitted atoms = 0.0000

− 6.7618 (0.0233) x − 2.9225 (0.0294) y + 10.9800 (0.0289) z = 0.2845 (0.0295)

Angle to previous plane (with approximate e.s.d.) = 4.94 (1.11)

* 0.0076 (0.0048) C1A * −0.0048 (0.0051) C2A * −0.0019 (0.0051) C3A * 0.0058 (0.0050) C4A * −0.0028 (0.0055) C5A * −0.0039 (0.0054) C6A

Rms deviation of fitted atoms = 0.0048

− 7.1155 (0.0520) x − 2.9413 (0.0393) y + 10.4335 (0.0632) z = 0.2553 (0.0253)

Angle to previous plane (with approximate e.s.d.) = 3.48 (0.73)

* 0.0000 (0.0000) N3 * 0.0000 (0.0000) N2 * 0.0000 (0.0000) N1

Rms deviation of fitted atoms = 0.0000

5.5093 (0.0236) x + 4.0238 (0.0253) y − 11.5604 (0.0205) z = 0.4091 (0.0117)

Angle to previous plane (with approximate e.s.d.) = 11.58 (0.65)

* −0.0069 (0.0042) C1B * 0.0050 (0.0047) C2B * 0.0027 (0.0048) C3B * −0.0086 (0.0046) C4B * 0.0066 (0.0045) C5B * 0.0012 (0.0044) C6B

Rms deviation of fitted atoms = 0.0057

5.1427 (0.0462) x + 4.5787 (0.1156) y − 11.4231 (0.1220) z = 0.5547 (0.0386)

Angle to previous plane (with approximate e.s.d.) = 3.30 (1.24)

* 0.0000 (0.0000) O1B * 0.0000 (0.0000) N5 * 0.0000 (0.0000) O2B

Rms deviation of fitted atoms = 0.0000

− 6.7618 (0.0233) x − 2.9225 (0.0294) y + 10.9800 (0.0289) z = 0.2845 (0.0295)

Angle to previous plane (with approximate e.s.d.) = 11.77 (1.06)

* 0.0076 (0.0048) C1A * −0.0048 (0.0051) C2A * −0.0019 (0.0051) C3A * 0.0058 (0.0050) C4A * −0.0028 (0.0055) C5A * −0.0039 (0.0054) C6A

Rms deviation of fitted atoms = 0.0048

5.5093 (0.0236) x + 4.0238 (0.0253) y − 11.5604 (0.0205) z = 0.4091 (0.0117)

Angle to previous plane (with approximate e.s.d.) = 8.93 (0.42)

* −0.0069 (0.0042) C1B * 0.0050 (0.0047) C2B * 0.0027 (0.0048) C3B * −0.0086 (0.0046) C4B * 0.0066 (0.0045) C5B * 0.0012 (0.0044) C6B

Rms deviation of fitted atoms = 0.0057

− 6.3657 (0.0087) x − 3.1303 (0.0047) y + 11.3320 (0.0084) z = 0.0744 (0.0046)

Angle to previous plane (with approximate e.s.d.) = 6.27 (0.30)

* 0.0095 (0.0049) O1A * −0.0280 (0.0054) N6 * −0.0782 (0.0066) O2A * 0.0450 (0.0056) C1A * −0.0392 (0.0072) C2A * −0.0745 (0.0068) C3A * −0.0311 (0.0061) C4A * 0.0317 (0.0074) C5A * 0.0677 (0.0072) C6A * 0.1032 (0.0047) N3 * 0.0039 (0.0044) N2 * 0.0655 (0.0046) N1 * 0.0197 (0.0051) C1B * 0.1239 (0.0066) C2B * 0.1032 (0.0068) C3B * −0.0298 (0.0059) C4B * −0.1614 (0.0059) C5B * −0.1312 (0.0056) C6B * 0.0684 (0.0057) O1B * −0.0686 (0.0061) N5

Rms deviation of fitted atoms = 0.0767

− 9.9485 (0.0063) x + 0.9374 (0.0282) y + 5.3709 (0.0353) z = 0.1036 (0.0236)

Angle to previous plane (with approximate e.s.d.) = 38.71 (0.19)

* −0.0049 (0.0041) C1C * 0.0095 (0.0044) C2C * −0.0058 (0.0048) C3C * −0.0025 (0.0048) C4C * 0.0071 (0.0049) C5C * −0.0034 (0.0046) C6C

Rms deviation of fitted atoms = 0.0060

2.1252 (0.0271) x − 6.7522 (0.0225) y + 11.0287 (0.0226) z = 0.7383 (0.0181)

Angle to previous plane (with approximate e.s.d.) = 89.25 (0.21)

* 0.0051 (0.0042) C1D * 0.0075 (0.0045) C2D * −0.0142 (0.0050) C3D * 0.0079 (0.0051) C4D * 0.0049 (0.0050) C5D * −0.0114 (0.0046) C6D

Rms deviation of fitted atoms = 0.0091

0.9741 (0.0414) x + 5.8984 (0.0319) y + 9.6600 (0.0357) z = 6.1329 (0.0078)

Angle to previous plane (with approximate e.s.d.) = 72.99 (1/5)

* 0.0051 (0.0051) C1E * 0.0020 (0.0053) C2E * −0.0072 (0.0060) C3E * 0.0055 (0.0073) C4E * 0.0015 (0.0082) C5E * −0.0069 (0.0067) C6E

Rms deviation of fitted atoms = 0.0052

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Au0.04392 (3)0.48136 (2)0.193131 (19)0.04855 (11)
N10.1232 (5)0.4729 (5)0.0738 (4)0.0362 (10)
N20.1732 (5)0.5756 (4)0.0686 (3)0.0341 (10)
N30.1045 (5)0.6639 (4)0.1404 (4)0.0357 (10)
C1A0.1527 (6)0.7755 (6)0.1390 (4)0.0364 (12)
C2A0.2665 (7)0.7906 (6)0.0718 (5)0.0486 (15)
H2A0.31610.72360.02250.058*
C3A0.3077 (7)0.9047 (6)0.0771 (5)0.0496 (15)
H3A0.38440.91450.03210.06*
C4A0.2315 (8)1.0034 (6)0.1509 (5)0.0460 (14)
C5A0.1167 (8)0.9917 (7)0.2177 (5)0.0552 (17)
H5A0.06651.05950.26620.066*
C6A0.0773 (8)0.8787 (7)0.2118 (5)0.0539 (17)
H6A0.00030.87020.25660.065*
N60.2785 (7)1.1216 (6)0.1574 (5)0.0543 (15)
O1A0.3852 (6)1.1250 (5)0.1018 (4)0.0644 (14)
O2A0.2052 (8)1.2113 (6)0.2190 (5)0.0844 (19)
C1B0.1939 (6)0.3699 (5)0.0015 (4)0.0364 (12)
C2B0.3204 (8)0.3624 (6)0.0624 (5)0.0493 (15)
H2B0.36130.43060.0590.059*
C3B0.3861 (9)0.2562 (8)0.1304 (5)0.063 (2)
H3B0.47080.25190.17280.076*
C4B0.3232 (9)0.1539 (6)0.1351 (5)0.0555 (19)
C5B0.1975 (8)0.1594 (6)0.0746 (5)0.0538 (17)
H5B0.15610.09180.07960.065*
C6B0.1321 (7)0.2676 (6)0.0053 (5)0.0464 (14)
H6B0.0470.27180.03660.056*
N50.3935 (11)0.0416 (8)0.2090 (5)0.078 (2)
O1B0.5043 (9)0.0394 (7)0.2598 (5)0.099 (3)
O2B0.3348 (10)0.0426 (7)0.2164 (6)0.106 (3)
P0.22000 (14)0.48593 (12)0.32131 (10)0.0300 (3)
C1C0.2678 (5)0.6348 (5)0.4035 (4)0.0305 (10)
C2C0.2551 (6)0.7473 (5)0.3632 (4)0.0369 (12)
H2C0.21690.74320.29670.044*
C3C0.2998 (8)0.8659 (6)0.4223 (5)0.0473 (15)
H3C0.29330.94110.3950.057*
C4C0.3537 (7)0.8720 (6)0.5218 (5)0.0451 (14)
H4C0.3830.9510.56140.054*
C5C0.3637 (7)0.7605 (7)0.5617 (5)0.0477 (15)
H5C0.39890.76450.62860.057*
C6C0.3224 (6)0.6430 (6)0.5036 (4)0.0412 (13)
H6C0.3310.56860.53150.049*
C1D0.3771 (6)0.4734 (5)0.2846 (4)0.0320 (11)
C2D0.5019 (6)0.5664 (6)0.3177 (5)0.0411 (13)
H2D0.50850.63760.36150.049*
C3D0.6172 (7)0.5522 (8)0.2848 (6)0.0576 (19)
H3D0.70060.61590.3050.069*
C4D0.6096 (8)0.4451 (8)0.2227 (6)0.0567 (18)
H4D0.68830.43510.2030.068*
C5D0.4849 (9)0.3522 (7)0.1896 (5)0.0552 (18)
H5D0.47960.280.14720.066*
C6D0.3683 (7)0.3665 (6)0.2193 (5)0.0456 (14)
H6D0.28390.30490.19590.055*
C1E0.1837 (6)0.3591 (5)0.3976 (4)0.0360 (11)
C2E0.2779 (7)0.2876 (6)0.4314 (5)0.0483 (15)
H2E0.36260.30330.41370.058*
C3E0.2459 (11)0.1952 (7)0.4902 (6)0.069 (2)
H3E0.30790.14670.5120.083*
C4E0.1159 (13)0.1734 (8)0.5179 (7)0.084 (3)
H4E0.09380.11160.5590.101*
C5E0.0294 (11)0.2392 (12)0.4860 (9)0.093 (3)
H5E0.05480.22340.50450.112*
C6E0.0580 (8)0.3334 (9)0.4247 (7)0.066 (2)
H6E0.00680.37880.40220.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au0.04395 (16)0.05158 (16)0.04696 (17)0.01641 (11)0.00138 (11)0.00027 (10)
N10.036 (2)0.038 (2)0.037 (2)0.0136 (19)0.007 (2)0.0094 (19)
N20.034 (2)0.033 (2)0.040 (3)0.0132 (18)0.013 (2)0.0095 (19)
N30.032 (2)0.037 (2)0.039 (3)0.0152 (19)0.005 (2)0.0060 (19)
C1A0.037 (3)0.041 (3)0.035 (3)0.017 (2)0.008 (2)0.007 (2)
C2A0.044 (3)0.042 (3)0.054 (4)0.021 (3)0.008 (3)0.000 (3)
C3A0.053 (4)0.050 (3)0.051 (4)0.029 (3)0.003 (3)0.009 (3)
C4A0.062 (4)0.044 (3)0.044 (3)0.027 (3)0.022 (3)0.009 (3)
C5A0.059 (4)0.050 (4)0.051 (4)0.021 (3)0.002 (3)0.011 (3)
C6A0.056 (4)0.054 (4)0.049 (4)0.028 (3)0.007 (3)0.002 (3)
N60.078 (4)0.046 (3)0.058 (4)0.033 (3)0.033 (3)0.016 (3)
O1A0.075 (4)0.065 (3)0.077 (4)0.047 (3)0.030 (3)0.023 (3)
O2A0.122 (6)0.056 (3)0.086 (4)0.047 (4)0.022 (4)0.002 (3)
C1B0.039 (3)0.039 (3)0.033 (3)0.009 (2)0.012 (2)0.010 (2)
C2B0.058 (4)0.044 (3)0.041 (3)0.010 (3)0.000 (3)0.013 (3)
C3B0.062 (5)0.069 (5)0.037 (4)0.012 (4)0.005 (3)0.018 (3)
C4B0.080 (5)0.043 (3)0.030 (3)0.012 (3)0.019 (3)0.000 (2)
C5B0.069 (5)0.041 (3)0.054 (4)0.005 (3)0.032 (4)0.001 (3)
C6B0.047 (4)0.041 (3)0.055 (4)0.011 (3)0.021 (3)0.006 (3)
N50.107 (7)0.063 (4)0.047 (4)0.020 (4)0.031 (4)0.002 (3)
O1B0.111 (6)0.098 (5)0.048 (4)0.032 (4)0.012 (4)0.013 (3)
O2B0.148 (8)0.058 (4)0.087 (5)0.006 (4)0.024 (5)0.020 (3)
P0.0272 (6)0.0302 (6)0.0321 (7)0.0122 (5)0.0014 (5)0.0008 (5)
C1C0.027 (2)0.031 (2)0.037 (3)0.0130 (19)0.008 (2)0.003 (2)
C2C0.048 (3)0.034 (3)0.030 (3)0.015 (2)0.010 (2)0.005 (2)
C3C0.065 (4)0.031 (3)0.050 (4)0.012 (3)0.021 (3)0.009 (2)
C4C0.046 (3)0.037 (3)0.047 (4)0.008 (2)0.007 (3)0.009 (2)
C5C0.052 (4)0.056 (4)0.032 (3)0.021 (3)0.002 (3)0.001 (3)
C6C0.046 (3)0.038 (3)0.037 (3)0.019 (2)0.004 (3)0.004 (2)
C1D0.036 (3)0.033 (2)0.032 (3)0.018 (2)0.007 (2)0.008 (2)
C2D0.039 (3)0.042 (3)0.045 (3)0.015 (2)0.013 (3)0.007 (2)
C3D0.032 (3)0.068 (4)0.081 (5)0.016 (3)0.022 (3)0.028 (4)
C4D0.062 (5)0.069 (4)0.063 (4)0.042 (4)0.034 (4)0.021 (4)
C5D0.075 (5)0.059 (4)0.049 (4)0.040 (4)0.026 (4)0.010 (3)
C6D0.048 (4)0.044 (3)0.045 (3)0.017 (3)0.009 (3)0.004 (3)
C1E0.033 (3)0.030 (2)0.042 (3)0.005 (2)0.006 (2)0.002 (2)
C2E0.055 (4)0.038 (3)0.057 (4)0.018 (3)0.014 (3)0.014 (3)
C3E0.108 (7)0.036 (3)0.067 (5)0.028 (4)0.013 (5)0.014 (3)
C4E0.109 (8)0.052 (5)0.070 (6)0.018 (5)0.019 (6)0.020 (4)
C5E0.067 (6)0.109 (8)0.103 (8)0.006 (6)0.042 (6)0.043 (7)
C6E0.036 (4)0.091 (6)0.077 (5)0.015 (4)0.021 (4)0.029 (4)
Geometric parameters (Å, º) top
Au—N12.108 (5)P—C1E1.812 (6)
Au—P2.2524 (13)P—C1D1.816 (5)
N1—N21.324 (6)C1C—C6C1.391 (8)
N1—C1B1.390 (8)C1C—C2C1.394 (7)
N2—N31.290 (7)C2C—C3C1.394 (8)
N3—C1A1.402 (7)C2C—H2C0.93
N3—C6Bi3.357 (8)C3C—C4C1.384 (10)
C1A—C2A1.386 (8)C3C—H3C0.93
C1A—C6A1.406 (9)C4C—C5C1.376 (9)
C2A—C3A1.392 (9)C4C—O1Biv3.304 (9)
C2A—H2A0.93C4C—H4C0.93
C3A—C4A1.387 (10)C5C—C6C1.378 (9)
C3A—H3A0.93C5C—H5C0.93
C4A—C5A1.378 (10)C6C—H6C0.93
C4A—N61.466 (8)C1D—C2D1.382 (9)
C5A—C6A1.371 (9)C1D—C6D1.394 (8)
C5A—H5A0.93C2D—C3D1.389 (9)
C6A—H6A0.93C2D—H2D0.93
N6—O1A1.211 (9)C3D—C4D1.374 (11)
N6—O2A1.227 (9)C3D—H3D0.93
N6—C6Bii3.282 (8)C4D—C5D1.380 (12)
C1B—C2B1.391 (9)C4D—H4D0.93
C1B—C6B1.401 (9)C5D—C6D1.380 (9)
C2B—C3B1.372 (10)C5D—O1Av3.330 (8)
C2B—H2B0.93C5D—H5D0.93
C3B—C4B1.405 (12)C6D—H6D0.93
C3B—H3B0.93C1E—C6E1.384 (9)
C4B—C5B1.368 (12)C1E—C2E1.398 (8)
C4B—N51.467 (9)C2E—C3E1.361 (10)
C5B—C6B1.395 (9)C2E—H2E0.93
C5B—H5B0.93C3E—C4E1.432 (15)
C6B—H6B0.93C3E—H3E0.93
N5—O1B1.198 (12)C4E—C5E1.289 (15)
N5—O2B1.209 (12)C4E—H4E0.93
N5—O1Aiii3.234 (9)C5E—C6E1.395 (13)
O1B—N6iii3.136 (9)C5E—H5E0.93
P—C1C1.809 (5)C6E—H6E0.93
N1—Au—P178.70 (13)C1D—P—Au112.76 (18)
N2—N1—C1B114.8 (5)C6C—C1C—C2C118.9 (5)
N2—N1—Au116.8 (4)C6C—C1C—P123.2 (4)
C1B—N1—Au128.3 (4)C2C—C1C—P117.9 (4)
N3—N2—N1110.4 (5)C3C—C2C—C1C120.2 (5)
N2—N3—C1A113.1 (5)C3C—C2C—H2C119.9
N2—N3—C6Bi85.1 (3)C1C—C2C—H2C119.9
C1A—N3—C6Bi101.1 (3)C4C—C3C—C2C120.1 (5)
C2A—C1A—N3125.0 (5)C4C—C3C—H3C120
C2A—C1A—C6A118.9 (5)C2C—C3C—H3C120
N3—C1A—C6A116.1 (5)C5C—C4C—C3C119.6 (5)
C1A—C2A—C3A120.9 (6)C5C—C4C—O1Biv89.5 (4)
C1A—C2A—H2A119.6C3C—C4C—O1Biv150.9 (4)
C3A—C2A—H2A119.6C5C—C4C—H4C120.2
C4A—C3A—C2A118.4 (6)C3C—C4C—H4C120.2
C4A—C3A—H3A120.8O1Biv—C4C—H4C30.7
C2A—C3A—H3A120.8C4C—C5C—C6C120.8 (6)
C5A—C4A—C3A121.9 (6)C4C—C5C—H5C119.6
C5A—C4A—N6120.3 (6)C6C—C5C—H5C119.6
C3A—C4A—N6117.8 (6)C5C—C6C—C1C120.5 (5)
C6A—C5A—C4A119.2 (6)C5C—C6C—H6C119.8
C6A—C5A—H5A120.4C1C—C6C—H6C119.8
C4A—C5A—H5A120.4C2D—C1D—C6D120.0 (5)
C5A—C6A—C1A120.8 (6)C2D—C1D—P122.3 (4)
C5A—C6A—H6A119.6C6D—C1D—P117.7 (5)
C1A—C6A—H6A119.6C1D—C2D—C3D119.3 (6)
O1A—N6—O2A124.4 (6)C1D—C2D—H2D120.4
O1A—N6—C4A118.4 (6)C3D—C2D—H2D120.4
O2A—N6—C4A117.1 (7)C4D—C3D—C2D120.8 (7)
O1A—N6—C6Bii83.6 (4)C4D—C3D—H3D119.6
O2A—N6—C6Bii87.7 (5)C2D—C3D—H3D119.6
C4A—N6—C6Bii98.7 (4)C3D—C4D—C5D119.9 (6)
N1—C1B—C2B124.4 (6)C3D—C4D—H4D120
N1—C1B—C6B116.6 (6)C5D—C4D—H4D120
C2B—C1B—C6B119.0 (6)C6D—C5D—C4D120.1 (6)
C3B—C2B—C1B121.2 (7)C6D—C5D—O1Av140.8 (5)
C3B—C2B—H2B119.4C4D—C5D—O1Av96.7 (4)
C1B—C2B—H2B119.4C6D—C5D—H5D120
C2B—C3B—C4B118.8 (7)C4D—C5D—H5D120
C2B—C3B—H3B120.6O1Av—C5D—H5D26.7
C4B—C3B—H3B120.6C5D—C6D—C1D119.9 (6)
C5B—C4B—C3B121.4 (6)C5D—C6D—H6D120
C5B—C4B—N5120.3 (8)C1D—C6D—H6D120
C3B—C4B—N5118.3 (8)C6E—C1E—C2E118.8 (6)
C4B—C5B—C6B119.2 (7)C6E—C1E—P118.4 (5)
C4B—C5B—H5B120.4C2E—C1E—P122.8 (5)
C6B—C5B—H5B120.4C3E—C2E—C1E120.2 (7)
C5B—C6B—C1B120.3 (7)C3E—C2E—H2E119.9
C5B—C6B—H6B119.8C1E—C2E—H2E119.9
C1B—C6B—H6B119.8C2E—C3E—C4E119.2 (8)
O1B—N5—O2B123.7 (8)C2E—C3E—H3E120.4
O1B—N5—C4B118.3 (10)C4E—C3E—H3E120.4
O2B—N5—C4B117.9 (10)C5E—C4E—C3E120.1 (8)
O1B—N5—O1Aiii75.9 (5)C5E—C4E—H4E119.9
O2B—N5—O1Aiii94.1 (5)C3E—C4E—H4E119.9
C4B—N5—O1Aiii101.8 (4)C4E—C5E—C6E122.1 (9)
N5—O1B—N6iii104.7 (5)C4E—C5E—H5E119
C1C—P—C1E104.9 (3)C6E—C5E—H5E119
C1C—P—C1D106.0 (2)C1E—C6E—C5E119.5 (8)
C1E—P—C1D105.8 (2)C1E—C6E—H6E120.2
C1C—P—Au111.92 (17)C5E—C6E—H6E120.2
C1E—P—Au114.72 (19)
Symmetry codes: (i) x, y+1, z; (ii) x, y+1, z; (iii) x1, y+1, z; (iv) x+1, y+1, z+1; (v) x+1, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4C—H4C···O1Biv0.932.553.304 (9)139
C5D—H5D···O1Av0.932.533.330 (8)144
Symmetry codes: (iv) x+1, y+1, z+1; (v) x+1, y1, z.

Experimental details

Crystal data
Chemical formula[Au(C12H8N5O4)(C18H15P)]
Mr745.47
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)10.2034 (4), 10.7550 (2), 14.0941 (5)
α, β, γ (°)93.987 (2), 102.148 (2), 103.930 (2)
V3)1455.73 (8)
Z2
Radiation typeMo Kα
µ (mm1)5.15
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correctionAnalytical
(Alcock, 1970)
Tmin, Tmax0.438, 0.648
No. of measured, independent and
observed [I > 2σ(I)] reflections
15644, 6639, 5647
Rint0.034
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.133, 1.09
No. of reflections6639
No. of parameters370
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.27, 1.20

Computer programs: COLLECT (Nonius BV, 1997-2000), HKL SCALEPACK (Otwinowski & Minor 1997), HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1996), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
Au—N12.108 (5)N6—O2A1.227 (9)
Au—P2.2524 (13)C4B—N51.467 (9)
N1—N21.324 (6)N5—O1B1.198 (12)
N1—C1B1.390 (8)N5—O2B1.209 (12)
N2—N31.290 (7)P—C1C1.809 (5)
N3—C1A1.402 (7)P—C1E1.812 (6)
C4A—N61.466 (8)P—C1D1.816 (5)
N6—O1A1.211 (9)
N1—Au—P178.70 (13)N3—N2—N1110.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4C—H4C···O1Bi0.932.553.304 (9)139
C5D—H5D···O1Aii0.932.533.330 (8)144
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y1, z.
 

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