Bromo­[(di­phenyl­phosphino-κP)(di­phenyl­phosphinoyl)­methane]­gold(I) aceto­nitrile solvate

In the title compound, [AuBr(dppmO)]·CH₃CN [dppmO = Ph₂P(CH₂)P(O)Ph₂], the dppmO ligand coordinates through the P donor to give a linear two-coordinate P—Au—Br gold(I) complex. The Au—Br and Au—P bond lengths are 2.241 (2) and 2.4069 (19) Å, respectively. The P—Au—Br and P=O groups lie almost parallel to each other [O—P...P—Au = 8.3 (2)°], while the intramolecular Au...O distance is 3.274 (4) Å.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.030
• wR factor = 0.079
• Data-to-parameter ratio = 20.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.65 Ratio
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....         C3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

Mixed bidentate phosphine–phosphine oxide ligands of general formula R₂P–Y–P(O)R₂, where Y is an organic spacer group, represent an important class of bidentate chelating ligands incorporating both soft (P) and hard (O) donor atoms (Grushin, 2001). Transition metal complexes of these ligands show a variety of structural forms (e.g. Coyle et al., 1998; Saravanabharathi et al., 2002; Faller & Parr, 2000) with evidence for both bidentate and monodentate coordination of the ligand to the metal atom.

We report here the structure of the acetonitrile solvate of the 1:1 complex of Ph₂P(CH₂)P(O)Ph₂ with gold(I) bromide, [(dppmO)AuBr]·CH₃CN, (I). The structure comprises discrete molecules of [(dppmO)AuBr] and acetonitrile separated by normal van der Waals distances (Fig. 1). The dppmO ligand coordinates to the gold through the P atom to yield a linear two-coordinate P—Au—Br geometry, with Au—P = 2.241 (2) Å, Au—Br = 2.4069 (19) Å and P—Au—Br = 178.53 (4)°. These parameters are similar to those recorded for other two-coordinate R₃PAuBr complexes (Bott et al., 2000). The P═O bond length of 1.490 (3) Å is also in accord with values recorded for other phosphine oxides (See et al., 1998).

The P—Au—Br and P═O groups lie almost parallel with the torsion angle O—P···P—Au 8.3 (2)°. For comparison, in the structure of the benzene solvate of the dioxide, dppmO₂ (Antipin et al., 1980), the P═O bonds are almost antiparallel, whereas in the structures of adducts of dppmO₂ with sodium halides (Hewertson et al., 1970; Ding et al., 2000) coordination of the O atoms to the sodium cation results in parallel P═O bonds and an Na···O distance of 2.457 (1) Å. An intermediate situation is observed for the structure of the 2:1 gold chloride complex with dppm, [(AuCl)₂(dppm)] (Schmidbaur et al., 1977), where the Au—P···P—Au torsion angle is 67 (1)°, with an Au···Au distance of 3.351 (2) Å, the latter suggestive of a significant aurophilic interaction. In the present complex, the intramolecular Au···O distance of 3.274 (4) Å is slightly longer than the Au···O distances for the [(tmpp)AuX] complexes [X = Cl, Br, I; tmpp = tris(2,4,6-trimethoxyphenyl)phosphine)] (Baker et al., 1995), which are in the range 2.92 (2)–3.15 (1) Å. This result, together with the absence of any significant distortion from linearity of the P–Au–Br bond, indicates the presence of only weak, if any, bonding interactions between the Au and O atoms and that the conformational structure of the complex is best ascribed as an outcome of crystal-packing considerations.

S2. Experimental

[NBu₄][AuBr₂] (50 mg, 0.072 mmol) and diphenylphosphinomethane mono-oxide (dppmO, 33.4 mg, 0.083 mmol) were dissolved in acetonitrile (10 ml) to give a clear solution. Slow evaporation of the solvent yielded well formed colorless crystals of (I); m.p. 506–507 K. The crystals slowly lost solvent over a period of weeks. Analysis found: C 46.0, H 3.5 N 1.7%; calculated for C₂₇H₂₅AuBrNOP₂: C 45.15, H 3.51, N 1.95%.ν_max (KBr)/cm⁻¹: 1179 (P═O str). δ_H (400 MHz, CDCl₃, p.p.m.): 3.53 [2H, dd, CH₂, ²J_P(Au)CH = 12 Hz, ²J_P(O)CH = 12 Hz], 7.36–7.47 (8H, m, m-C₆H₅), 7.42–7.55 (4H, m, p-C₆H₅), 7.66–7.75 (8H, m, o-C₆H₅). δ_C (100 MHz, CDCl₃, p.p.m.): 31.4 [dd, CH₂, ¹J_CP(O) = 59 Hz, ¹J_CP(Au) = 26 Hz], 129.4 [d, m-C₆H₅(PAu), ³J_CP(Au) = 12 Hz], 129.4 [d, m-C₆H₅(PO), ³J_CP(Au) = 12 Hz], 129.7 [dd, i-C₆H₅(PAu), ¹J_CP(Au) = 61 Hz, ³J_CP(O) = 4 Hz], 131.2 [d, o-C₆H₅(PAu), ²J_CP(Au) = 10 Hz], 131.9 [dd, i-C₆H₅(PO), ¹J_CP(O) = 105 Hz, ³J_CP(Au) = 3 Hz], 132.3 [d, p-C₆H₅(PAu), ⁴J_CP(Au) = 3 Hz], 132.9 [d, p-C₆H₅(PO), ⁴J_CP(O) = 3 Hz], 133.7 [d, o-C₆H₅(PO), ²J_CP(Au) = 15 Hz], δ_P (162 MHz, CDCl₃, p.p.m.): 25.0 [1P, s, P(O)]; 20.0 [1P, s,P(Au)].

S3. Refinement

H atoms were constrained in the riding model approximation, fixed to their parent C atoms at a C—H distance of 0.95 Å, and U_iso(H) values were set to 1.2U_eq of the parent atom.

Computing details

Data collection: MSC/AFC7 Diffractometer Control Software for Windows (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control Software for Windows; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON (Spek, 1980-2001).

Figures

Fig. 1. View of the title compound with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.

Bromo[(diphenylphosphino-κP)(diphenylphosphinoyl)methane]gold(I) acetonitrile solvate

Crystal data

[AuBr(C25H22OP2)]·CH3CN	F(000) = 1384
Mr = 718.29	Dx = 1.811 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.657 (3) Å	θ = 12.5–17.4°
b = 22.436 (17) Å	µ = 7.24 mm^−1
c = 11.209 (4) Å	T = 295 K
β = 115.98 (2)°	Prismatic, colorless
V = 2635 (2) Å^3	0.30 × 0.30 × 0.20 mm
Z = 4

Data collection

Rigaku AFC-7R diffractometer	4561 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.027
Graphite monochromator	θmax = 27.5°, θmin = 2.7°
ω scans	h = −13→15
Absorption correction: ψ scan (North, Phillips & Matthews, 1968)	k = 0→29
Tmin = 0.135, Tmax = 0.235	l = −14→5
6598 measured reflections	3 standard reflections every 150 reflections
6045 independent reflections	intensity decay: 5.0%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters not refined
wR(F^2) = 0.079	w = 1/[σ^2(Fo^2) + (0.0339P)^2 + 2.0179P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
6045 reflections	Δρmax = 1.05 e Å^−3
299 parameters	Δρmin = −1.07 e Å^−3
0 restraints	Extinction correction: SHELXL97, FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00103 (10)

Special details

Experimental. The scan width was (1.10 + 0.30tanθ)° with an ω scan speed of 16° per minute (up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Au1	0.51548 (2)	0.15206 (1)	0.36269 (2)	0.0379 (1)
Br1	0.45026 (7)	0.13005 (3)	0.13186 (5)	0.0628 (2)
P1	0.57349 (10)	0.17046 (5)	0.57799 (11)	0.0278 (3)
P2	0.80322 (10)	0.24324 (5)	0.59582 (10)	0.0255 (3)
O1	0.7611 (3)	0.24140 (15)	0.4497 (3)	0.0369 (10)
C1	0.6725 (4)	0.23675 (19)	0.6413 (4)	0.0260 (11)
C111	0.4400 (4)	0.1847 (2)	0.6170 (4)	0.0304 (11)
C112	0.3166 (5)	0.1779 (3)	0.5204 (5)	0.0482 (18)
C113	0.2152 (5)	0.1850 (3)	0.5522 (7)	0.064 (2)
C114	0.2365 (5)	0.1990 (3)	0.6787 (6)	0.054 (2)
C115	0.3591 (5)	0.2072 (3)	0.7753 (6)	0.0520 (19)
C116	0.4601 (4)	0.2002 (2)	0.7445 (5)	0.0436 (16)
C121	0.6556 (4)	0.10800 (19)	0.6854 (4)	0.0288 (12)
C122	0.6357 (5)	0.0516 (2)	0.6289 (5)	0.0438 (17)
C123	0.6863 (6)	0.0022 (2)	0.7077 (6)	0.057 (2)
C124	0.7597 (6)	0.0085 (3)	0.8415 (6)	0.059 (2)
C125	0.7827 (5)	0.0641 (3)	0.8966 (5)	0.0548 (17)
C126	0.7316 (5)	0.1145 (2)	0.8200 (5)	0.0387 (16)
C211	0.8857 (4)	0.31148 (19)	0.6707 (4)	0.0299 (12)
C212	0.9970 (4)	0.3232 (2)	0.6555 (5)	0.0405 (17)
C213	1.0645 (5)	0.3748 (3)	0.7077 (6)	0.0489 (17)
C214	1.0242 (5)	0.4150 (3)	0.7737 (5)	0.0549 (19)
C215	0.9150 (6)	0.4041 (3)	0.7871 (6)	0.0544 (19)
C216	0.8458 (5)	0.3522 (2)	0.7367 (5)	0.0443 (17)
C221	0.9130 (4)	0.1838 (2)	0.6805 (4)	0.0309 (12)
C222	0.9135 (5)	0.1336 (2)	0.6098 (6)	0.0458 (17)
C223	0.9950 (6)	0.0868 (3)	0.6725 (8)	0.066 (2)
C224	1.0770 (6)	0.0912 (3)	0.8036 (7)	0.069 (3)
C225	1.0785 (6)	0.1409 (3)	0.8750 (6)	0.065 (2)
C226	0.9966 (5)	0.1877 (3)	0.8146 (5)	0.0428 (16)
N1	0.2404 (10)	0.0100 (5)	0.5836 (9)	0.131 (4)
C2	0.4154 (8)	0.0355 (4)	0.8112 (10)	0.101 (4)
C3	0.3168 (9)	0.0220 (4)	0.6819 (10)	0.083 (3)
H11	0.61940	0.27080	0.60830	0.0310*
H12	0.70740	0.23610	0.73550	0.0310*
H112	0.30110	0.16840	0.43210	0.0580*
H113	0.13030	0.18020	0.48550	0.0760*
H114	0.16650	0.20290	0.70010	0.0650*
H115	0.37380	0.21770	0.86290	0.0620*
H116	0.54460	0.20610	0.81120	0.0520*
H122	0.58710	0.04710	0.53580	0.0520*
H123	0.67020	−0.03640	0.66910	0.0680*
H124	0.79430	−0.02570	0.89560	0.0700*
H125	0.83480	0.06830	0.98920	0.0650*
H126	0.74840	0.15300	0.85950	0.0470*
H212	1.02550	0.29570	0.60970	0.0480*
H213	1.14000	0.38270	0.69780	0.0590*
H214	1.07200	0.45030	0.81000	0.0660*
H215	0.88630	0.43220	0.83120	0.0650*
H216	0.77080	0.34480	0.74770	0.0530*
H222	0.85800	0.13120	0.51770	0.0550*
H223	0.99360	0.05180	0.62440	0.0790*
H224	1.13410	0.05930	0.84600	0.0840*
H225	1.13600	0.14320	0.96650	0.0780*
H226	0.99740	0.22220	0.86400	0.0510*
H21	0.38350	0.03040	0.87540	0.1210*
H22	0.48570	0.00940	0.83110	0.1210*
H23	0.44250	0.07560	0.81320	0.1210*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.0416 (1)	0.0435 (1)	0.0264 (1)	−0.0076 (1)	0.0129 (1)	−0.0052 (1)
Br1	0.0873 (4)	0.0667 (4)	0.0301 (3)	−0.0218 (3)	0.0217 (3)	−0.0120 (3)
P1	0.0266 (5)	0.0317 (6)	0.0241 (5)	−0.0024 (4)	0.0102 (4)	−0.0028 (4)
P2	0.0277 (5)	0.0290 (6)	0.0204 (5)	−0.0016 (4)	0.0110 (4)	0.0001 (4)
O1	0.0457 (18)	0.047 (2)	0.0189 (14)	−0.0025 (15)	0.0150 (13)	0.0015 (14)
C1	0.0263 (19)	0.028 (2)	0.0225 (19)	0.0009 (16)	0.0095 (16)	−0.0008 (17)
C111	0.0278 (19)	0.030 (2)	0.033 (2)	−0.0042 (17)	0.0130 (17)	−0.0003 (18)
C112	0.033 (2)	0.071 (4)	0.037 (3)	−0.002 (2)	0.012 (2)	−0.001 (3)
C113	0.032 (3)	0.087 (5)	0.070 (4)	0.001 (3)	0.019 (3)	0.002 (4)
C114	0.044 (3)	0.060 (4)	0.071 (4)	0.004 (3)	0.037 (3)	0.006 (3)
C115	0.053 (3)	0.060 (4)	0.057 (3)	−0.005 (3)	0.037 (3)	−0.013 (3)
C116	0.037 (2)	0.056 (3)	0.040 (3)	−0.007 (2)	0.019 (2)	−0.015 (2)
C121	0.029 (2)	0.027 (2)	0.032 (2)	−0.0006 (17)	0.0149 (17)	0.0007 (18)
C122	0.048 (3)	0.034 (3)	0.042 (3)	0.000 (2)	0.013 (2)	−0.008 (2)
C123	0.067 (4)	0.033 (3)	0.063 (4)	0.007 (3)	0.021 (3)	−0.005 (3)
C124	0.069 (4)	0.041 (3)	0.059 (4)	0.016 (3)	0.022 (3)	0.010 (3)
C125	0.062 (3)	0.051 (3)	0.041 (3)	0.004 (3)	0.013 (3)	0.005 (3)
C126	0.047 (3)	0.033 (3)	0.028 (2)	0.000 (2)	0.009 (2)	−0.0035 (19)
C211	0.035 (2)	0.029 (2)	0.025 (2)	−0.0051 (18)	0.0124 (17)	−0.0002 (17)
C212	0.044 (3)	0.043 (3)	0.036 (3)	−0.007 (2)	0.019 (2)	−0.003 (2)
C213	0.045 (3)	0.048 (3)	0.054 (3)	−0.017 (2)	0.022 (2)	−0.002 (3)
C214	0.066 (4)	0.046 (3)	0.043 (3)	−0.025 (3)	0.015 (3)	−0.008 (3)
C215	0.079 (4)	0.044 (3)	0.047 (3)	−0.010 (3)	0.034 (3)	−0.013 (3)
C216	0.052 (3)	0.043 (3)	0.047 (3)	−0.010 (2)	0.030 (2)	−0.008 (2)
C221	0.029 (2)	0.035 (2)	0.032 (2)	−0.0008 (18)	0.0164 (18)	0.0022 (19)
C222	0.049 (3)	0.041 (3)	0.050 (3)	0.007 (2)	0.024 (2)	−0.002 (2)
C223	0.078 (4)	0.040 (3)	0.091 (5)	0.019 (3)	0.048 (4)	0.009 (3)
C224	0.068 (4)	0.071 (5)	0.082 (5)	0.041 (4)	0.045 (4)	0.039 (4)
C225	0.053 (3)	0.093 (5)	0.046 (3)	0.027 (3)	0.019 (3)	0.028 (3)
C226	0.045 (3)	0.055 (3)	0.030 (2)	0.008 (2)	0.018 (2)	0.006 (2)
N1	0.145 (8)	0.152 (9)	0.099 (6)	−0.007 (7)	0.055 (6)	−0.015 (6)
C2	0.092 (6)	0.098 (7)	0.115 (7)	0.002 (5)	0.048 (6)	−0.009 (6)
C3	0.101 (6)	0.072 (5)	0.098 (6)	0.003 (5)	0.064 (5)	0.000 (5)

Geometric parameters (Å, º)

Au1—Br1	2.4069 (19)	C213—C214	1.373 (9)
Au1—P1	2.241 (2)	C214—C215	1.368 (10)
P1—C1	1.825 (5)	C114—H114	0.9500
P1—C111	1.820 (5)	C115—H115	0.9495
P1—C121	1.822 (5)	C215—C216	1.388 (8)
P2—O1	1.490 (3)	C116—H116	0.9495
P2—C1	1.812 (5)	C221—C226	1.390 (7)
P2—C211	1.807 (5)	C221—C222	1.379 (7)
P2—C221	1.804 (5)	C222—C223	1.383 (9)
N1—C3	1.105 (14)	C122—H122	0.9498
C1—H11	0.9503	C223—C224	1.361 (11)
C1—H12	0.9509	C123—H123	0.9494
C111—C116	1.387 (7)	C224—C225	1.368 (10)
C111—C112	1.379 (7)	C124—H124	0.9513
C112—C113	1.385 (9)	C225—C226	1.381 (9)
C113—C114	1.365 (9)	C125—H125	0.9502
C114—C115	1.376 (9)	C126—H126	0.9511
C115—C116	1.373 (8)	C2—H21	0.9506
C121—C122	1.388 (6)	C2—H23	0.9505
C121—C126	1.383 (7)	C2—H22	0.9508
C122—C123	1.378 (7)	C212—H212	0.9508
C123—C124	1.370 (9)	C213—H213	0.9507
C124—C125	1.365 (9)	C214—H214	0.9511
C125—C126	1.387 (8)	C215—H215	0.9480
C2—C3	1.433 (14)	C216—H216	0.9495
C211—C216	1.378 (7)	C222—H222	0.9498
C211—C212	1.405 (7)	C223—H223	0.9486
C212—C213	1.378 (8)	C224—H224	0.9508
C112—H112	0.9492	C225—H225	0.9495
C113—H113	0.9496	C226—H226	0.9494
Au1···O1	3.274 (4)	C221···H212	3.0926
Au1···C123^i	4.063 (6)	C222···H114^vi	3.0862
Au1···C115^ii	3.562 (7)	C225···H114^vi	2.9313
Au1···C116^ii	3.523 (5)	C226···H114^vi	2.8130
Au1···H122	2.9305	H11···Br1^iv	3.0597
Au1···H123^i	3.2969	H11···H216	2.4283
Au1···H222	3.6197	H11···C216	3.0073
Au1···H112	2.9475	H12···C126	2.8611
Au1···H115^ii	3.3570	H12···C116	3.0371
Au1···H116^ii	3.2784	H12···H126	2.2482
Br1···H22^i	3.2011	H12···C216	3.0609
Br1···H11^ii	3.0597	H12···H116	2.4870
O1···Au1	3.274 (4)	H12···O1^iv	2.2571
O1···C1^ii	3.183 (6)	H12···H216	2.5346
O1···H222	2.6862	H22···Br1^i	3.2011
O1···H12^ii	2.2571	H23···C115	3.0792
O1···H116^ii	2.5950	H23···C116	2.9306
O1···H126^ii	2.5547	H112···Au1	2.9475
N1···H215^iii	2.7159	H112···C213^vii	2.9657
C1···O1^iv	3.183 (6)	H113···C214^vii	3.0258
C1···H126	2.8982	H114···C222^viii	3.0862
C1···H116	2.9682	H114···C221^viii	2.8975
C1···H216	2.7230	H114···H212^viii	2.5698
C3···H215^iii	3.0629	H114···C225^viii	2.9313
C115···Au1^iv	3.562 (7)	H114···C226^viii	2.8130
C116···C126	3.476 (8)	H115···Au1^iv	3.3571
C116···Au1^iv	3.523 (5)	H116···H12	2.4870
C121···C222	3.510 (9)	H116···H126	2.4959
C121···C221	3.470 (7)	H116···Au1^iv	3.2784
C123···Au1^i	4.063 (6)	H116···C126	2.9659
C126···C226	3.522 (9)	H116···C1	2.9682
C126···C221	3.497 (8)	H116···O1^iv	2.5950
C126···C116	3.476 (8)	H122···Au1	2.9305
C212···C226	3.526 (8)	H123···Au1^i	3.2969
C115···H23	3.0792	H124···H213^ix	2.5707
C116···H23	2.9306	H125···C214^iv	3.0027
C116···H12	3.0371	H125···C213^iv	3.0087
C221···C126	3.497 (8)	H126···C1	2.8982
C221···C121	3.470 (7)	H126···H12	2.2482
C222···C121	3.510 (9)	H126···H116	2.4959
C126···H116	2.9659	H126···O1^iv	2.5547
C226···C212	3.526 (8)	H212···H114^vi	2.5698
C126···H12	2.8611	H212···C221	3.0926
C226···C126	3.522 (9)	H213···H124^x	2.5707
C211···H226	2.8161	H215···C3^xi	3.0629
C213···H112^v	2.9657	H215···N1^xi	2.7159
C213···H125^ii	3.0087	H216···H11	2.4283
C214···H125^ii	3.0027	H216···H12	2.5346
C214···H113^v	3.0258	H216···C1	2.7230
C215···H222^iv	3.0421	H222···C215^ii	3.0421
C216···H12	3.0609	H222···Au1	3.6197
C216···H11	3.0073	H222···O1	2.6862
C221···H114^vi	2.8975	H226···C211	2.8161
Br1—Au1—P1	178.53 (4)	C114—C115—H115	120.11
Au1—P1—C1	114.21 (15)	C116—C115—H115	120.14
Au1—P1—C111	113.87 (14)	C111—C116—H116	119.66
Au1—P1—C121	113.16 (14)	C211—C216—C215	120.1 (6)
C1—P1—C111	103.0 (2)	C115—C116—H116	119.60
C1—P1—C121	108.1 (2)	P2—C221—C222	118.8 (4)
C111—P1—C121	103.5 (2)	C222—C221—C226	119.7 (5)
O1—P2—C1	113.2 (2)	P2—C221—C226	121.5 (4)
O1—P2—C211	112.7 (2)	C221—C222—C223	120.2 (6)
O1—P2—C221	112.0 (2)	C121—C122—H122	119.88
C1—P2—C211	106.2 (2)	C123—C122—H122	120.03
C1—P2—C221	106.4 (2)	C222—C223—C224	119.6 (6)
C211—P2—C221	105.8 (2)	C124—C123—H123	119.80
P1—C1—P2	115.0 (2)	C122—C123—H123	119.85
P2—C1—H11	108.09	C125—C124—H124	120.28
P1—C1—H11	108.10	C223—C224—C225	120.9 (7)
P1—C1—H12	108.02	C123—C124—H124	120.11
P2—C1—H12	108.07	C124—C125—H125	119.32
H11—C1—H12	109.48	C126—C125—H125	119.42
P1—C111—C112	120.0 (4)	C224—C225—C226	120.3 (6)
P1—C111—C116	121.0 (4)	C221—C226—C225	119.3 (6)
C112—C111—C116	119.0 (5)	C125—C126—H126	120.49
C111—C112—C113	120.0 (5)	C121—C126—H126	120.44
C112—C113—C114	120.4 (6)	C3—C2—H22	109.52
C113—C114—C115	120.1 (6)	C3—C2—H23	109.57
C114—C115—C116	119.7 (6)	H21—C2—H23	109.41
C111—C116—C115	120.7 (5)	H22—C2—H23	109.51
P1—C121—C126	122.7 (3)	H21—C2—H22	109.33
P1—C121—C122	117.7 (3)	C3—C2—H21	109.50
C122—C121—C126	119.5 (4)	C211—C212—H212	120.23
C121—C122—C123	120.1 (5)	C213—C212—H212	120.33
C122—C123—C124	120.3 (5)	C212—C213—H213	119.52
C123—C124—C125	119.6 (6)	C214—C213—H213	119.54
C124—C125—C126	121.3 (5)	C213—C214—H214	120.18
C121—C126—C125	119.1 (4)	C215—C214—H214	120.06
N1—C3—C2	177.9 (11)	C216—C215—H215	119.69
P2—C211—C216	125.1 (4)	C214—C215—H215	119.76
C212—C211—C216	119.2 (4)	C211—C216—H216	120.01
P2—C211—C212	115.7 (3)	C215—C216—H216	119.86
C111—C112—H112	120.02	C223—C222—H222	119.89
C113—C112—H112	120.00	C221—C222—H222	119.92
C211—C212—C213	119.4 (5)	C222—C223—H223	120.17
C212—C213—C214	120.9 (6)	C224—C223—H223	120.19
C114—C113—H113	119.78	C223—C224—H224	119.47
C112—C113—H113	119.79	C225—C224—H224	119.63
C113—C114—H114	119.87	C224—C225—H225	119.88
C213—C214—C215	119.8 (6)	C226—C225—H225	119.85
C115—C114—H114	120.00	C221—C226—H226	120.33
C214—C215—C216	120.5 (6)	C225—C226—H226	120.40
Au1—P1—C1—P2	−46.7 (3)	H112—C112—C113—H113	0.21
C111—P1—C1—P2	−170.7 (2)	C111—C112—C113—H113	−179.86
C121—P1—C1—P2	80.2 (3)	H112—C112—C113—C114	−179.62
Au1—P1—C111—C112	6.2 (5)	H113—C113—C114—H114	1.59
Au1—P1—C111—C116	−176.3 (3)	H113—C113—C114—C115	−178.70
C1—P1—C111—C112	130.5 (4)	C212—C213—C214—C215	−0.6 (9)
C1—P1—C111—C116	−52.0 (4)	C112—C113—C114—H114	−178.58
C121—P1—C111—C112	−117.0 (4)	H114—C114—C115—C116	178.55
C121—P1—C111—C116	60.5 (4)	C113—C114—C115—H115	178.78
Au1—P1—C121—C122	−22.2 (5)	C213—C214—C215—C216	1.2 (9)
Au1—P1—C121—C126	160.4 (4)	H114—C114—C115—H115	−1.52
C1—P1—C121—C122	−149.7 (4)	C114—C115—C116—H116	179.65
C1—P1—C121—C126	32.9 (5)	H115—C115—C116—C111	179.81
C111—P1—C121—C122	101.5 (4)	H115—C115—C116—H116	−0.29
C111—P1—C121—C126	−75.9 (5)	C214—C215—C216—C211	−1.0 (8)
O1—P2—C1—P1	56.1 (3)	C126—C121—C122—H122	−176.85
C211—P2—C1—P1	−179.7 (2)	P1—C121—C126—H126	−4.83
C221—P2—C1—P1	−67.3 (3)	P1—C121—C122—H122	5.71
O1—P2—C211—C212	−59.8 (4)	P2—C221—C222—C223	−178.8 (5)
O1—P2—C211—C216	118.5 (4)	C226—C221—C222—C223	1.3 (9)
C1—P2—C211—C212	175.7 (3)	P2—C221—C226—C225	179.8 (5)
C1—P2—C211—C216	−6.0 (4)	C222—C221—C226—C225	−0.3 (9)
C221—P2—C211—C212	62.9 (4)	C122—C121—C126—H126	177.86
C221—P2—C211—C216	−118.9 (4)	C221—C222—C223—C224	−1.7 (11)
O1—P2—C221—C222	−22.1 (5)	C121—C122—C123—H123	177.98
O1—P2—C221—C226	157.7 (4)	H122—C122—C123—C124	178.03
C1—P2—C221—C222	102.1 (5)	H122—C122—C123—H123	−1.99
C1—P2—C221—C226	−78.1 (5)	H123—C123—C124—C125	179.96
C211—P2—C221—C222	−145.3 (4)	H123—C123—C124—H124	−0.12
C211—P2—C221—C226	34.6 (5)	C222—C223—C224—C225	1.1 (12)
P2—C211—C212—C213	178.9 (4)	C122—C123—C124—H124	179.86
P1—C111—C112—H112	−4.22	C223—C224—C225—C226	−0.2 (11)
C116—C111—C112—H112	178.24	H124—C124—C125—H125	1.09
P1—C111—C116—H116	4.26	C123—C124—C125—H125	−178.98
C216—C211—C212—C213	0.5 (7)	H124—C124—C125—C126	−178.98
P2—C211—C216—C215	−178.1 (4)	C224—C225—C226—C221	−0.2 (10)
C212—C211—C216—C215	0.1 (7)	C124—C125—C126—H126	−179.92
C112—C111—C116—H116	−178.23	H125—C125—C126—C121	−179.82
C211—C212—C213—C214	−0.3 (8)	H125—C125—C126—H126	0.02

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, −y+1/2, z−1/2; (iii) −x+1, y−1/2, −z+3/2; (iv) x, −y+1/2, z+1/2; (v) x+1, −y+1/2, z+1/2; (vi) x+1, y, z; (vii) x−1, −y+1/2, z−1/2; (viii) x−1, y, z; (ix) −x+2, y−1/2, −z+3/2; (x) −x+2, y+1/2, −z+3/2; (xi) −x+1, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H12···O1^iv	0.95	2.26	3.183 (6)	164
C116—H116···O1^iv	0.95	2.60	3.500 (7)	159
C126—H126···O1^iv	0.95	2.55	3.499 (6)	172

Symmetry code: (iv) x, −y+1/2, z+1/2.