Chlorido{N-[2-(diphenyl­phosphan­yl)benz­yl]-1-(pyridin-2-yl)methanamine-κP}gold(I)

Traut, T.; Kriel, F.H.; Zyl, W.E. van; Williams, D.B.G.

doi:10.1107/S1600536811044205

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1625

doi:10.1107/S1600536811044205

Open

access

Chlorido{N-[2-(diphenylphosphanyl)benzyl]-1-(pyridin-2-yl)methanamine-κP}gold(I)

Telisha Traut,^a,^b Frederik H. Kriel,^b Werner E. van Zyl ^a ‡ and D. Bradley G. Williams ^a ^*§

^aDepartment of Chemistry, University of Johannesburg, PO Box 524, Auckland Park 2006, South Africa, and ^bBiomed, Mintek, Private Bag X3015, Randburg 2125, South Africa
^*Correspondence e-mail: bwilliams@uj.ac.za

(Received 17 October 2011; accepted 24 October 2011; online 29 October 2011)

In the title compound, [AuCl(C₂₅H₂₃N₂P)], the Au^I atom is in a typical almost linear coordination environment defined by phosphane P and Cl atoms [bond angle = 175.48 (4)°]. Helical supramolecular chains along the b axis and mediated by N—H⋯Cl hydrogen bonds feature in the crystal packing.

Related literature

For previously published crystal structures of related P,N-type Au(I) complexes, see: Williams et al. (2007 ). For catalytic reactions of these types of complexes, see: Williams & Pretorius (2008 ). For related structures, see: Baenziger et al. (1976 ); Bellon et al. (1969 ). For the synthesis of the ligand, see: Shirakawa et al. (1997 ).

Experimental

Crystal data

[AuCl(C₂₅H₂₃N₂P)]
M_r = 614.84
Monoclinic, P 2₁ /n
a = 12.5888 (9) Å
b = 14.1443 (10) Å
c = 13.2354 (11) Å
β = 107.128 (3)°
V = 2252.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 6.74 mm⁻¹
T = 173 K
0.40 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: integration (SADABS; Bruker, 1999 ) T_min = 0.303, T_max = 0.559
13864 measured reflections
5572 independent reflections
4399 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.067
S = 0.97
5572 reflections
275 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.96 e Å⁻³
Δρ_min = −1.30 e Å⁻³

Table 1
Selected bond lengths (Å)

Au1—P1	2.2410 (10)
Au1—Cl1	2.2921 (10)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1ⁱ	0.87 (6)	2.68 (5)	3.536 (4)	169 (5)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811044205/tk5001sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811044205/tk5001Isup2.hkl

checkCIF report

Comment top

We have previously published crystal structure data regarding three related P,N type Au(I) complexes, two of which exhibited inter- and intra-molecular gold—gold interactions, as well as displaying differential gold binding affinity for the phosphorus and nitrogen atoms, respectively (Williams et al., 2007). These complexes were obtained as a part of our continued interest in the versatility and transition metal complexation of heteroditopic, multifunctional P,N-based ligands. We are especially interested in this class of compounds for their proven efficiency as catalysts in certain chemical reactions (Williams et al., 2008), as well as for their potential in medicinal applications, an aspect which has not received much attention in literature..

As a part of this on-going study, we have prepared an amino-phosphine ligand (II) from 2-(diphenylphosphanyl)benzaldehyde as starting material (I), proceeding via the Schiff base which is reduced to amine (II). This P,N product formed the crystalline title Au(I) complex (III) from a saturated chloroform solution. This complex is of particular interest as the two N atoms should in theory have different gold binding affinities due to the difference in the state of their hybridization (sp² vs sp³), in keeping with previously published results (Williams, et al., 2007).

The title compound (III), Fig. 1, crystallizes in the monoclinic space group P2₁/c. The crystal packing is stabilized by weak intra-molecular N—H···Cl interactions (Fig. 2). The coordination at the gold metal centre showed a virtually linear P—Au—Cl system (bond angle of 175.48 (4)°) as is common for two-coordinate Au(I) compounds. The Au—P distance of 2.241 (1) Å compares favourably to the Au—P distance in the similar (triphenylphosphine)gold(I) chloride structure of 2.235 (3) Å (Baenziger et al., 1976), but is shorter than the corresponding bond distance in the related (triphenylphosphine)gold(I) cyanide of 2.27 (1) Å (Bellon et al., 1969). As expected, the Au—Cl distance of 2.292 (1) Å compares well with that observed for (triphenylphosphine)gold(I) chloride at 2.279 (3) Å.

Related literature top

For previously published crystal structures of related P,N-type Au(I) complexes, see: Williams et al. (2007). For catalytic reactions of these types of complexes, see: Williams & Pretorius (2008). For related structures, see: Baenziger et al. (1976); Bellon et al. (1969). For the synthesis of the ligand, see: Shirakawa et al. (1997).

Experimental top

The ligand (II) was synthesized in a similar manner to a literature procedure (Shirakawa et al., 1997) and the title compound was prepared as per previously described methods (Williams et al., 2007).

The amino-phosphine ligand (II) employed in this study was prepared from the 2-(diphenylphosphanyl)benzaldehyde starting material (I). The synthesis involved reacting (I) (300 mg, 0.689 mmol) with 1.5 equivalents of 2-(aminomethyl)pyridine (0.106 ml, 1.033 mmol) in toluene (15 ml) as solvent. The reaction mixture was stirred under reflux (oil bath temperature 140–150 °C) for 5 h, after which the solvent was removed in vacuo. The intermediate imino-phosphine product was dissolved in dried MeOH (10 ml). NaBH₄ (3 equivalents) was added and the reaction mixture stirred at room temperature for 15 h. The reduction reaction was quenched by the addition of deionized H₂O, and the mixture was extracted with H₂O and DCM and the resultant organic phase dried over Na₂SO₄. Solids were removed via filtration and the solvent removed in vacuo. The pure amino-phosphine ligand (II) was recovered in high yield (85%) after bulb-to-bulb vacuum distillation.

Amino-phosphine ligand (II) (120 mg, 0.314 mmol) was dissolved in 20 mL of diethyl ether. To this solution were added 0.95 equivalents of (THT)AuCl (96 mg, 0.298 mmol) dissolved in 2 mL of chloroform. The (THT)AuCl solution was slowly added to the ligand solution and the mixture stirred at room temperature for 5 minutes. The solvent was evaporated in vacuo to ca 5 ml and the white, powdered product (III) was precipitated from the solution by the addition of 10 ml cold hexane (x3). Colourless monoclinic crystals were grown from a chloroform solution of the product. Yield 108 mg, 56%. ¹H NMR (CDCl₃, 300 MHz, p.p.m.) 8.41 [d, J = 4.5 Hz, 1H, aromatic], 7.64 [dd, J = 6.6 and 5.4 Hz, 1H, aromatic], 7.57–7.36 [m, 11H, aromatic], 7.20 [d, J = 7.2 Hz, 2H, aromatic], 7.13–7.06 [m, 2H, aromatic], 6.81 [dd, J = 12.8 and 4.1 Hz, 1H, aromatic], 4.20 [s, 2H, Ar—CH₂N], 3.68 [s, 2H, NCH₂], 1.81 [s, NH]. ¹³C{¹H} NMR: (CDCl₃, 75 MHz, p.p.m.) 158.8 [s, 1 C], 149.1 [s, 1 C], 144.1 [d, J_C,P = 10.9 Hz, 1 C], 136.4 [s, 1 C], 134.1 [d, J_C,P = 13.8 Hz, 4 C], 133.9 [d, J_C,P = 7.1 Hz, 1 C], 131.8 [d, J_C,P = 2.3 Hz, 1 C], 131.6 [d, J_C,P = 2.3 Hz, 2 C], 130.3 [d, J_C,P = 8.9 Hz, 1 C], 129.8 [s, 1 C], 129.1 [d, J_C,P = 11.8 Hz, 4 C], 128.1 [d, J_C,P = 16.3 Hz, 1 C], 127.3 [d, J_C,P = 10.0 Hz, 1 C], 126.7 [d, J_C,P = 59.0 Hz, 1 C], 122.4 [s, 1 C], 121.8 [s, 1 C], 54.1 [s, 1 C], 52.5 [d, J_C,P = 16.3 Hz, 1 C]. ³¹P{¹H} NMR (CDCl₃, 121.42 MHz, p.p.m.): 26.7 [s].

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. Molecular structure of the title compound drawn with dispacement ellipsoids at the 50% probability level. Hydrogen atoms have been omitted for clarity.

Chlorido{N-[2-(diphenylphosphanyl)benzyl]-1-(pyridin-2-yl)methanamine- κP}gold(I) top

Crystal data top

[AuCl(C₂₅H₂₃N₂P)]	Z = 4
M_r = 614.84	F(000) = 1192
Monoclinic, P2₁/n	D_x = 1.813 Mg m⁻³
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.5888 (9) Å	µ = 6.74 mm⁻¹
b = 14.1443 (10) Å	T = 173 K
c = 13.2354 (11) Å	Needle, colourless
β = 107.128 (3)°	0.40 × 0.18 × 0.16 mm
V = 2252.2 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	5572 independent reflections
Radiation source: sealed tube	4399 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
phi and ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: integration (SADABS; Bruker, 1999)	h = −15→16
T_min = 0.303, T_max = 0.559	k = −14→18
13864 measured reflections	l = −17→13

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ²(F_o²) + (0.0307P)²] where P = (F_o² + 2F_c²)/3
5572 reflections	(Δ/σ)_max = 0.001
275 parameters	Δρ_max = 1.96 e Å⁻³
0 restraints	Δρ_min = −1.30 e Å⁻³

Crystal data top

[AuCl(C₂₅H₂₃N₂P)]	V = 2252.2 (3) Å³
M_r = 614.84	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.5888 (9) Å	µ = 6.74 mm⁻¹
b = 14.1443 (10) Å	T = 173 K
c = 13.2354 (11) Å	0.40 × 0.18 × 0.16 mm
β = 107.128 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5572 independent reflections
Absorption correction: integration (SADABS; Bruker, 1999)	4399 reflections with I > 2σ(I)
T_min = 0.303, T_max = 0.559	R_int = 0.056
13864 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Δρ_max = 1.96 e Å⁻³
5572 reflections	Δρ_min = −1.30 e Å⁻³
275 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
C11	0.3621 (3)	0.3261 (3)	−0.0026 (3)	0.0274 (8)
C12	0.3958 (3)	0.2313 (3)	0.0098 (4)	0.0334 (9)
H12	0.3973	0.1994	0.0716	0.040*
C13	0.4266 (3)	0.1849 (3)	−0.0686 (4)	0.0394 (10)
H13	0.4504	0.1224	−0.0591	0.047*
C14	0.4222 (3)	0.2317 (3)	−0.1619 (4)	0.0395 (11)
H14	0.4421	0.2001	−0.2152	0.047*
C15	0.3883 (3)	0.3247 (4)	−0.1758 (3)	0.0374 (10)
H15	0.3854	0.3558	−0.2384	0.045*
C16	0.3585 (3)	0.3719 (3)	−0.0958 (3)	0.0323 (9)
H16	0.3360	0.4347	−0.1052	0.039*
C21	0.2684 (3)	0.4968 (3)	0.0550 (3)	0.0247 (8)
C22	0.1574 (3)	0.5053 (3)	−0.0094 (3)	0.0304 (9)
H22	0.1113	0.4525	−0.0237	0.036*
C23	0.1170 (3)	0.5929 (3)	−0.0515 (3)	0.0373 (10)
H23	0.0441	0.5982	−0.0945	0.045*
C24	0.1844 (4)	0.6721 (3)	−0.0297 (3)	0.0376 (10)
H24	0.1567	0.7305	−0.0578	0.045*
C25	0.2925 (3)	0.6644 (3)	0.0336 (4)	0.0396 (11)
H25	0.3376	0.7178	0.0482	0.048*
C26	0.3350 (3)	0.5775 (3)	0.0758 (3)	0.0330 (9)
H26	0.4083	0.5731	0.1183	0.040*
C31	0.4514 (3)	0.3993 (3)	0.2079 (3)	0.0257 (8)
C32	0.5495 (3)	0.4040 (3)	0.1776 (3)	0.0313 (9)
H32	0.5454	0.3985	0.1065	0.038*
C33	0.6517 (3)	0.4168 (3)	0.2519 (4)	0.0348 (10)
H33	0.7159	0.4200	0.2308	0.042*
C34	0.6584 (3)	0.4249 (3)	0.3571 (4)	0.0414 (11)
H34	0.7273	0.4333	0.4070	0.050*
C35	0.5637 (3)	0.4205 (3)	0.3893 (4)	0.0380 (10)
H35	0.5694	0.4270	0.4606	0.046*
C36	0.4582 (3)	0.4061 (3)	0.3152 (3)	0.0289 (9)
C37	0.3585 (3)	0.3989 (3)	0.3553 (3)	0.0337 (9)
H37A	0.3271	0.3359	0.3413	0.040*
H37B	0.3814	0.4087	0.4312	0.040*
C38	0.1744 (3)	0.4593 (3)	0.3383 (3)	0.0351 (9)
H38A	0.1951	0.4629	0.4148	0.042*
H38B	0.1420	0.3974	0.3175	0.042*
C39	0.0880 (3)	0.5339 (3)	0.2923 (3)	0.0322 (9)
C40	0.0988 (3)	0.5991 (3)	0.2179 (3)	0.0332 (9)
H40	0.1613	0.5989	0.1940	0.040*
C41	0.0137 (3)	0.6655 (3)	0.1792 (4)	0.0402 (11)
H41	0.0190	0.7098	0.1290	0.048*
C42	−0.0769 (3)	0.6645 (3)	0.2160 (4)	0.0444 (12)
H42	−0.1338	0.7084	0.1920	0.053*
C43	−0.0821 (4)	0.5968 (4)	0.2897 (4)	0.0489 (13)
H43	−0.1446	0.5961	0.3137	0.059*
P1	0.31973 (7)	0.38097 (7)	0.10429 (8)	0.0245 (2)
Cl1	0.06264 (8)	0.17656 (7)	0.15389 (8)	0.0337 (2)
Au1	0.193361 (11)	0.282466 (10)	0.135160 (12)	0.02541 (5)
N1	0.2738 (3)	0.4689 (3)	0.3046 (3)	0.0327 (8)
N2	−0.0018 (3)	0.5310 (3)	0.3295 (3)	0.0449 (10)
H1	0.307 (4)	0.523 (4)	0.319 (4)	0.045 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.0214 (16)	0.028 (2)	0.032 (2)	−0.0037 (15)	0.0072 (15)	−0.0029 (18)
C12	0.039 (2)	0.028 (2)	0.036 (2)	0.0002 (16)	0.0145 (18)	−0.0009 (18)
C13	0.036 (2)	0.034 (2)	0.050 (3)	−0.0009 (18)	0.016 (2)	−0.007 (2)
C14	0.033 (2)	0.051 (3)	0.038 (3)	−0.0051 (19)	0.0151 (18)	−0.017 (2)
C15	0.031 (2)	0.053 (3)	0.029 (2)	0.0008 (19)	0.0112 (17)	0.002 (2)
C16	0.0264 (19)	0.037 (2)	0.034 (2)	0.0003 (16)	0.0101 (17)	0.0055 (19)
C21	0.0259 (17)	0.025 (2)	0.022 (2)	0.0030 (14)	0.0057 (15)	0.0003 (16)
C22	0.0282 (18)	0.031 (2)	0.029 (2)	−0.0028 (16)	0.0026 (16)	−0.0034 (18)
C23	0.030 (2)	0.041 (3)	0.035 (2)	0.0055 (18)	0.0004 (17)	0.002 (2)
C24	0.044 (2)	0.031 (2)	0.036 (3)	0.0088 (19)	0.0098 (19)	0.005 (2)
C25	0.038 (2)	0.025 (2)	0.053 (3)	−0.0047 (17)	0.008 (2)	0.002 (2)
C26	0.0251 (18)	0.033 (2)	0.035 (2)	−0.0007 (16)	0.0003 (16)	0.0041 (19)
C31	0.0264 (17)	0.022 (2)	0.027 (2)	0.0022 (14)	0.0049 (15)	0.0038 (16)
C32	0.0315 (19)	0.028 (2)	0.032 (2)	0.0012 (16)	0.0061 (17)	0.0045 (18)
C33	0.0224 (17)	0.035 (2)	0.044 (3)	0.0026 (16)	0.0042 (17)	0.006 (2)
C34	0.030 (2)	0.037 (3)	0.047 (3)	0.0009 (17)	−0.0056 (19)	0.002 (2)
C35	0.041 (2)	0.036 (3)	0.029 (2)	0.0055 (18)	−0.0014 (18)	0.003 (2)
C36	0.0312 (19)	0.025 (2)	0.029 (2)	0.0053 (15)	0.0056 (16)	0.0025 (17)
C37	0.037 (2)	0.031 (2)	0.033 (2)	0.0028 (17)	0.0109 (18)	0.0035 (19)
C38	0.040 (2)	0.034 (2)	0.033 (2)	−0.0014 (18)	0.0140 (18)	0.0005 (19)
C39	0.0318 (19)	0.028 (2)	0.038 (2)	−0.0055 (16)	0.0120 (18)	−0.0112 (19)
C40	0.034 (2)	0.028 (2)	0.038 (2)	−0.0069 (17)	0.0109 (18)	−0.0106 (19)
C41	0.037 (2)	0.032 (3)	0.047 (3)	−0.0057 (18)	0.004 (2)	−0.009 (2)
C42	0.031 (2)	0.035 (3)	0.061 (3)	−0.0015 (18)	0.004 (2)	−0.015 (2)
C43	0.033 (2)	0.047 (3)	0.070 (4)	−0.007 (2)	0.020 (2)	−0.017 (3)
P1	0.0234 (4)	0.0238 (5)	0.0260 (5)	0.0000 (4)	0.0068 (4)	0.0013 (4)
Cl1	0.0320 (5)	0.0304 (5)	0.0425 (6)	−0.0029 (4)	0.0168 (4)	0.0038 (5)
Au1	0.02563 (8)	0.02361 (8)	0.02855 (9)	−0.00060 (6)	0.01040 (6)	0.00008 (6)
N1	0.0344 (17)	0.027 (2)	0.036 (2)	0.0019 (15)	0.0107 (15)	0.0005 (16)
N2	0.042 (2)	0.035 (2)	0.062 (3)	−0.0060 (17)	0.0234 (19)	−0.011 (2)

Geometric parameters (Å, º) top

C11—C16	1.383 (6)	C32—H32	0.9300
C11—C12	1.401 (6)	C33—C34	1.375 (6)
C11—P1	1.825 (4)	C33—H33	0.9300
C12—C13	1.377 (6)	C34—C35	1.381 (6)
C12—H12	0.9300	C34—H34	0.9300
C13—C14	1.387 (7)	C35—C36	1.414 (5)
C13—H13	0.9300	C35—H35	0.9300
C14—C15	1.378 (7)	C36—C37	1.503 (6)
C14—H14	0.9300	C37—N1	1.465 (5)
C15—C16	1.394 (6)	C37—H37A	0.9700
C15—H15	0.9300	C37—H37B	0.9700
C16—H16	0.9300	C38—N1	1.454 (5)
C21—C26	1.394 (5)	C38—C39	1.508 (6)
C21—C22	1.412 (5)	C38—H38A	0.9700
C21—P1	1.811 (4)	C38—H38B	0.9700
C22—C23	1.391 (6)	C39—N2	1.360 (5)
C22—H22	0.9300	C39—C40	1.385 (6)
C23—C24	1.384 (6)	C40—C41	1.402 (6)
C23—H23	0.9300	C40—H40	0.9300
C24—C25	1.377 (6)	C41—C42	1.366 (6)
C24—H24	0.9300	C41—H41	0.9300
C25—C26	1.390 (6)	C42—C43	1.382 (7)
C25—H25	0.9300	C42—H42	0.9300
C26—H26	0.9300	C43—N2	1.361 (6)
C31—C36	1.400 (6)	C43—H43	0.9300
C31—C32	1.407 (5)	Au1—P1	2.2410 (10)
C31—P1	1.832 (4)	Au1—Cl1	2.2921 (10)
C32—C33	1.383 (5)	N1—H1	0.86 (5)

C16—C11—C12	118.8 (4)	C33—C34—H34	119.7
C16—C11—P1	123.5 (3)	C35—C34—H34	119.7
C12—C11—P1	117.7 (3)	C34—C35—C36	120.8 (4)
C13—C12—C11	120.7 (4)	C34—C35—H35	119.6
C13—C12—H12	119.6	C36—C35—H35	119.6
C11—C12—H12	119.6	C31—C36—C35	118.6 (4)
C12—C13—C14	119.8 (4)	C31—C36—C37	123.0 (3)
C12—C13—H13	120.1	C35—C36—C37	118.4 (4)
C14—C13—H13	120.1	N1—C37—C36	111.3 (3)
C15—C14—C13	120.3 (4)	N1—C37—H37A	109.4
C15—C14—H14	119.9	C36—C37—H37A	109.4
C13—C14—H14	119.9	N1—C37—H37B	109.4
C14—C15—C16	119.8 (4)	C36—C37—H37B	109.4
C14—C15—H15	120.1	H37A—C37—H37B	108.0
C16—C15—H15	120.1	N1—C38—C39	113.2 (4)
C11—C16—C15	120.5 (4)	N1—C38—H38A	108.9
C11—C16—H16	119.7	C39—C38—H38A	108.9
C15—C16—H16	119.7	N1—C38—H38B	108.9
C26—C21—C22	118.7 (3)	C39—C38—H38B	108.9
C26—C21—P1	122.6 (3)	H38A—C38—H38B	107.7
C22—C21—P1	118.6 (3)	N2—C39—C40	122.9 (4)
C23—C22—C21	119.8 (4)	N2—C39—C38	114.2 (4)
C23—C22—H22	120.1	C40—C39—C38	122.9 (4)
C21—C22—H22	120.1	C39—C40—C41	118.8 (4)
C24—C23—C22	120.6 (4)	C39—C40—H40	120.6
C24—C23—H23	119.7	C41—C40—H40	120.6
C22—C23—H23	119.7	C42—C41—C40	119.4 (5)
C25—C24—C23	119.8 (4)	C42—C41—H41	120.3
C25—C24—H24	120.1	C40—C41—H41	120.3
C23—C24—H24	120.1	C41—C42—C43	118.5 (4)
C24—C25—C26	120.6 (4)	C41—C42—H42	120.8
C24—C25—H25	119.7	C43—C42—H42	120.8
C26—C25—H25	119.7	N2—C43—C42	124.2 (4)
C25—C26—C21	120.4 (3)	N2—C43—H43	117.9
C25—C26—H26	119.8	C42—C43—H43	117.9
C21—C26—H26	119.8	C21—P1—C11	105.08 (18)
C36—C31—C32	119.3 (3)	C21—P1—C31	106.85 (17)
C36—C31—P1	122.7 (3)	C11—P1—C31	103.51 (17)
C32—C31—P1	118.0 (3)	C21—P1—Au1	115.56 (12)
C33—C32—C31	121.0 (4)	C11—P1—Au1	105.18 (13)
C33—C32—H32	119.5	C31—P1—Au1	119.07 (13)
C31—C32—H32	119.5	P1—Au1—Cl1	175.48 (4)
C34—C33—C32	119.9 (4)	C38—N1—C37	111.9 (3)
C34—C33—H33	120.1	C38—N1—H1	115 (3)
C32—C33—H33	120.1	C37—N1—H1	105 (3)
C33—C34—C35	120.5 (4)	C39—N2—C43	116.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1ⁱ	0.87 (6)	2.68 (5)	3.536 (4)	169 (5)

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[AuCl(C₂₅H₂₃N₂P)]
M_r	614.84
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	12.5888 (9), 14.1443 (10), 13.2354 (11)
β (°)	107.128 (3)
V (Å³)	2252.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.74
Crystal size (mm)	0.40 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Integration (SADABS; Bruker, 1999)
T_min, T_max	0.303, 0.559
No. of measured, independent and observed [I > 2σ(I)] reflections	13864, 5572, 4399
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.067, 0.97
No. of reflections	5572
No. of parameters	275
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.96, −1.30

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Au1—P1

2.2410 (10)

Au1—Cl1

2.2921 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1ⁱ	0.87 (6)	2.68 (5)	3.536 (4)	169 (5)

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Footnotes

‡Current address: School of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa.

§Additional address: Industrial Research Limited, 69 Gracefield Road, Lower Hutt 5040, New Zealand.

Acknowledgements

The authors thank AuTEK Biomed (Mintek and Harmony Gold) and the University of Johannesburg for financial support. We also thank the University of the Witwatersrand for the use of their X-ray diffractometer.

References

Baenziger, N. C., Bennett, W. E. & Soborofe, D. M. (1976). Acta Cryst. B32, 962–963. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Bellon, P. L., Manassero, M. & Sansoni, M. (1969). Ric. Sci. 39, 173–175. CAS Google Scholar
Bruker (1999). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shirakawa, E., Yoshida, H. & Takaya, H. (1997). Tetrahedron Lett. 38, 3759–3762. CrossRef CAS Web of Science Google Scholar
Williams, D. B. G. & Pretorius, M. (2008). J. Mol. Catal. A Chem. 284, 77–84. Web of Science CrossRef CAS Google Scholar
Williams, D. B. G., Traut, T., Kriel, F. H. & Van Zyl, W. E. (2007). Inorg. Chem. Commun. 10, 538–542. Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.