metal-organic compounds
Chlorido{N-[2-(diphenylphosphanyl)benzylidene]-2,6-diisopropylaniline-κP}gold(I) chloroform 0.25-solvate
aDepartment of Chemistry, University of Cape Town, Private Bag, Rondebosch, 7707, South Africa, and bResearch Centre for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg (APK Campus), PO Box 524, Auckland Park, Johannesburg, 2006, South Africa
*Correspondence e-mail: harrychiririwa@yahoo.com
The 31H32NP)]·0.25CHCl3, contains two independent complex molecules and half a chloroform solvent molecule, which is disordered across an inversion center. The AuI ions are each coordinated in a slightly distorted linear environment, with P—Au—Cl angles of 177.20 (4) and 178.54 (4)°.
of the title compound, [AuCl(CRelated literature
For general background to gold complexes, see: Shaw (1999); Barnard et al. (2004); Nomiya et al. (2003). For applications of gold-containing drugs, see: Chiririwa et al. (2013); Fricker (1996); Cowan (1993); Parish (1992); Finkelstein et al. (1976). For the synthesis of the starting materials, see: Mogorosi et al. (2011); Uson & Laguna (1986); Reddy et al. (2002). For similar compounds, see: Chiririwa & Muller (2012); Williams et al. (2007).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT and XPREP (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
https://doi.org/10.1107/S1600536812049975/lh5564sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049975/lh5564Isup2.hkl
The iminophosphine ligand was synthesized in high yields from the Schiff-base condensation reaction of 2-(diphenylphosphanyl)benzaldehyde with 2,6-diisopropylaniline in CH2Cl2 at room temperature (Mogorosi et al., 2011; Reddy et al., 2002). The Au precursor was synthesized by slow drop wise addition of tetrahydrothiophene (THT) to a solution of HAuCl4.4H2O in EtOH (Uson & Laguna, 1986). To a dry CH2Cl2 (10 ml) solution of the precursor [Au(tht)Cl] (tht = tetrahydrothiophene) was added an equimolar amount of 2-(diphenylphosphanyl)benzylidene)-2,6 diisopropylbenzenamine in CH2Cl2 (10 ml), and stirred at room temperature for 2 hrs. The solvent was reduced under reduced pressure and on addition of hexane, the product was filtered off and washed with Et2O (2 × 5 ml) and dried under vacuum for 4 hrs affording a yellow precipitate. Crystals suitable for X-ray
were obtained by recrystallization from a CHCl3/hexane mixture at room temperature. 31P NMR: 26.64 (s). IR (KBr): 1628 cm-1 (C=N, imine).All H atoms were included in calculated positions with C—H = 0.95–1.00 Å and included in the
with Uiso(H) = 1.2Ueq(C) or 1.5 Ueq(Cmethyl). The chloroform solvate molecule is disordered over an inversion centre, H atom connectivity was correctly assigned by using a PART -1 instruction in SHELXL97 (Sheldrick, 2008). Occupancies of each disordered component was constrained to 50% conforming to the imposed No additional geometrical or thermal ellipsoid restraints were employed in the final cycles.Studies of gold(I) complexes have been related to anti-arthritic (Shaw, 1999), anti-tumor (Barnard et al., 2004) and antimicrobial physiological activities (Nomiya et al., 2003). The treatment of diseases with gold complexes (called chrysotherapy) can be traced back to early times (Cowan, 1993). The mechanistic approach regarding the action of gold drugs is still a matter of interest and research, however they remain the most effective second line treatment for rheumatoid arthritis (Parish, 1992; Fricker, 1996). This led to the development of a gold complex called auranofin, which was found to be an experimental chrysotherapeutic agent and was clinically effective in the treatment of rheumatoid arthritis (Finkelstein et al., 1976). Our group has recently been involved in the development of novel Au(I) complexes with iminophosphine ligands and these have shown promising activity when evaluated against two oesophageal cancer cell lines (Chiririwa et al., 2013).
The structure of the title compound (Fig. 1) was determined to establish the coordination properties of the 2-(diphenylphosphanyl)benzylidene)- 2,6-diisopropylbenzenamine ligand with gold. The
consists of two crystallographically independent complex molecules. The Au—P bond distances of 2.2354 (10) and 2.2267 (10) Å agree well with reported values (Williams et al.., 2007; Chiririwa & Muller, 2012). The chloroform solvent molecule is disordered across an inversion centre.For general background to gold complexes, see: Shaw (1999); Barnard et al. (2004); Nomiya et al. (2003). For applications of gold-containing drugs, see: Chiririwa et al. (2013); Fricker (1996); Cowan (1993); Parish (1992); Finkelstein et al. (1976). For the synthesis of the starting materials, see: Mogorosi et al. (2011); Uson & Laguna (1986); Reddy et al. (2002). For similar compounds, see: Chiririwa & Muller (2012); Williams et al. (2007).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT and XPREP (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 2012).[AuCl(C31H32NP)]·0.25CHCl3 | Z = 4 |
Mr = 711.81 | F(000) = 1402 |
Triclinic, P1 | Dx = 1.619 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.0315 (3) Å | Cell parameters from 119370 reflections |
b = 13.3638 (2) Å | θ = 2.3–26.4° |
c = 19.3489 (5) Å | µ = 5.27 mm−1 |
α = 96.358 (2)° | T = 173 K |
β = 99.229 (1)° | Block, yellow |
γ = 116.191 (1)° | 0.21 × 0.18 × 0.12 mm |
V = 2921.15 (11) Å3 |
Bruker APEXII 4K CCD diffractometer | 11945 independent reflections |
Radiation source: fine-focus sealed tube | 9894 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
Detector resolution: 0 pixels mm-1 | θmax = 26.4°, θmin = 1.8° |
0.5° ω scans, 20s | h = −16→16 |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | k = −16→16 |
Tmin = 0.404, Tmax = 0.570 | l = −24→24 |
119407 measured reflections |
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.065 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0042P)2 + 7.7368P] where P = (Fo2 + 2Fc2)/3 |
11945 reflections | (Δ/σ)max = 0.001 |
667 parameters | Δρmax = 1.91 e Å−3 |
0 restraints | Δρmin = −1.54 e Å−3 |
[AuCl(C31H32NP)]·0.25CHCl3 | γ = 116.191 (1)° |
Mr = 711.81 | V = 2921.15 (11) Å3 |
Triclinic, P1 | Z = 4 |
a = 13.0315 (3) Å | Mo Kα radiation |
b = 13.3638 (2) Å | µ = 5.27 mm−1 |
c = 19.3489 (5) Å | T = 173 K |
α = 96.358 (2)° | 0.21 × 0.18 × 0.12 mm |
β = 99.229 (1)° |
Bruker APEXII 4K CCD diffractometer | 11945 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 9894 reflections with I > 2σ(I) |
Tmin = 0.404, Tmax = 0.570 | Rint = 0.053 |
119407 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.065 | H-atom parameters constrained |
S = 1.09 | Δρmax = 1.91 e Å−3 |
11945 reflections | Δρmin = −1.54 e Å−3 |
667 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Au1A | 0.261779 (14) | −0.032391 (14) | −0.065469 (8) | 0.03058 (5) | |
Cl1A | 0.21007 (11) | −0.10467 (11) | −0.18529 (6) | 0.0472 (3) | |
P1A | 0.31961 (9) | 0.03622 (9) | 0.05254 (5) | 0.0273 (2) | |
N1A | 0.3385 (3) | 0.3431 (3) | −0.0152 (2) | 0.0425 (10) | |
C1A | 0.2277 (4) | 0.3255 (4) | −0.0571 (2) | 0.0371 (10) | |
C2A | 0.2036 (4) | 0.2940 (4) | −0.1316 (2) | 0.0364 (10) | |
C3A | 0.1033 (4) | 0.2912 (4) | −0.1706 (3) | 0.0453 (12) | |
H3A | 0.0857 | 0.2723 | −0.2214 | 0.054* | |
C4A | 0.0285 (5) | 0.3153 (5) | −0.1376 (3) | 0.0545 (14) | |
H4A | −0.0395 | 0.3134 | −0.1656 | 0.065* | |
C5A | 0.0515 (5) | 0.3418 (5) | −0.0643 (3) | 0.0545 (14) | |
H5A | −0.0017 | 0.3567 | −0.0420 | 0.065* | |
C6A | 0.1513 (4) | 0.3473 (5) | −0.0222 (3) | 0.0516 (13) | |
C7A | 0.2839 (5) | 0.2630 (6) | −0.1691 (3) | 0.0581 (15) | |
H7A | 0.3212 | 0.2312 | −0.1348 | 0.070* | |
C8A | 0.3811 (7) | 0.3648 (6) | −0.1823 (5) | 0.109 (3) | |
H8AA | 0.4306 | 0.3420 | −0.2060 | 0.163* | |
H8AB | 0.4284 | 0.4175 | −0.1366 | 0.163* | |
H8AC | 0.3486 | 0.4027 | −0.2129 | 0.163* | |
C9A | 0.2199 (7) | 0.1711 (6) | −0.2367 (4) | 0.101 (3) | |
H9AA | 0.1552 | 0.1052 | −0.2266 | 0.152* | |
H9AB | 0.2749 | 0.1478 | −0.2532 | 0.152* | |
H9AC | 0.1883 | 0.2009 | −0.2739 | 0.152* | |
C10A | 0.1770 (6) | 0.3745 (7) | 0.0610 (3) | 0.088 (2) | |
H10A | 0.2204 | 0.3334 | 0.0792 | 0.106* | |
C11A | 0.2554 (10) | 0.4963 (9) | 0.0867 (5) | 0.182 (6) | |
H11D | 0.3256 | 0.5183 | 0.0674 | 0.273* | |
H11E | 0.2786 | 0.5131 | 0.1391 | 0.273* | |
H11F | 0.2145 | 0.5391 | 0.0710 | 0.273* | |
C12A | 0.0687 (8) | 0.3357 (7) | 0.0899 (4) | 0.100 (3) | |
H12D | 0.0156 | 0.2550 | 0.0688 | 0.150* | |
H12E | 0.0288 | 0.3809 | 0.0778 | 0.150* | |
H12F | 0.0908 | 0.3458 | 0.1420 | 0.150* | |
C13A | 0.3428 (4) | 0.2607 (4) | 0.0059 (2) | 0.0348 (10) | |
H13A | 0.2735 | 0.1893 | −0.0062 | 0.042* | |
C14A | 0.4531 (3) | 0.2695 (4) | 0.0498 (2) | 0.0280 (9) | |
C15A | 0.4521 (3) | 0.1752 (3) | 0.0765 (2) | 0.0267 (9) | |
C16A | 0.5551 (3) | 0.1859 (4) | 0.1187 (2) | 0.0307 (9) | |
H16A | 0.5548 | 0.1230 | 0.1374 | 0.037* | |
C17A | 0.6582 (4) | 0.2884 (4) | 0.1334 (2) | 0.0371 (11) | |
H17A | 0.7282 | 0.2953 | 0.1621 | 0.044* | |
C18A | 0.6599 (4) | 0.3801 (4) | 0.1066 (3) | 0.0417 (11) | |
H18A | 0.7308 | 0.4498 | 0.1164 | 0.050* | |
C19A | 0.5574 (4) | 0.3704 (4) | 0.0651 (2) | 0.0359 (10) | |
H19A | 0.5588 | 0.4340 | 0.0469 | 0.043* | |
C20A | 0.2136 (3) | 0.0562 (3) | 0.0959 (2) | 0.0288 (9) | |
C21A | 0.0961 (4) | −0.0217 (4) | 0.0732 (2) | 0.0375 (11) | |
H21A | 0.0700 | −0.0828 | 0.0337 | 0.045* | |
C22A | 0.0160 (4) | −0.0103 (4) | 0.1083 (3) | 0.0446 (12) | |
H22A | −0.0651 | −0.0640 | 0.0928 | 0.054* | |
C23A | 0.0530 (4) | 0.0783 (4) | 0.1654 (3) | 0.0428 (12) | |
H23A | −0.0025 | 0.0857 | 0.1891 | 0.051* | |
C24A | 0.1711 (4) | 0.1566 (4) | 0.1885 (2) | 0.0371 (10) | |
H24A | 0.1970 | 0.2176 | 0.2282 | 0.045* | |
C25A | 0.2513 (4) | 0.1454 (4) | 0.1533 (2) | 0.0322 (10) | |
H25A | 0.3323 | 0.1992 | 0.1687 | 0.039* | |
C26A | 0.3579 (3) | −0.0571 (3) | 0.0989 (2) | 0.0290 (9) | |
C27A | 0.4052 (5) | −0.1184 (4) | 0.0658 (3) | 0.0465 (12) | |
H27A | 0.4157 | −0.1116 | 0.0187 | 0.056* | |
C28A | 0.4372 (6) | −0.1890 (5) | 0.0999 (3) | 0.0604 (16) | |
H28A | 0.4719 | −0.2287 | 0.0771 | 0.073* | |
C29A | 0.4188 (5) | −0.2016 (4) | 0.1671 (3) | 0.0534 (14) | |
H29A | 0.4393 | −0.2515 | 0.1903 | 0.064* | |
C30A | 0.3709 (4) | −0.1429 (4) | 0.2010 (3) | 0.0461 (12) | |
H30A | 0.3582 | −0.1523 | 0.2474 | 0.055* | |
C31A | 0.3413 (4) | −0.0699 (4) | 0.1674 (2) | 0.0402 (11) | |
H31A | 0.3095 | −0.0282 | 0.1912 | 0.048* | |
Au1B | 0.513749 (14) | 0.777609 (13) | 0.449875 (8) | 0.02904 (5) | |
Cl1B | 0.50551 (13) | 0.74084 (11) | 0.33113 (6) | 0.0508 (3) | |
P1B | 0.52319 (9) | 0.81829 (9) | 0.56620 (5) | 0.0251 (2) | |
N1B | 0.1566 (3) | 0.5623 (3) | 0.4766 (2) | 0.0439 (10) | |
C1B | 0.1405 (4) | 0.4560 (4) | 0.4387 (2) | 0.0387 (11) | |
C2B | 0.0953 (4) | 0.4264 (4) | 0.3643 (2) | 0.0385 (11) | |
C3B | 0.0748 (4) | 0.3211 (4) | 0.3282 (3) | 0.0420 (12) | |
H3B | 0.0450 | 0.3002 | 0.2778 | 0.050* | |
C4B | 0.0964 (5) | 0.2467 (4) | 0.3637 (3) | 0.0533 (14) | |
H4B | 0.0822 | 0.1753 | 0.3380 | 0.064* | |
C5B | 0.1392 (5) | 0.2762 (4) | 0.4374 (3) | 0.0544 (14) | |
H5B | 0.1538 | 0.2240 | 0.4615 | 0.065* | |
C6B | 0.1614 (4) | 0.3803 (4) | 0.4770 (2) | 0.0452 (13) | |
C7B | 0.0733 (4) | 0.5084 (4) | 0.3238 (3) | 0.0469 (12) | |
H7B | 0.0749 | 0.5696 | 0.3595 | 0.056* | |
C8B | −0.0477 (5) | 0.4502 (5) | 0.2709 (4) | 0.079 (2) | |
H8BA | −0.0584 | 0.5062 | 0.2460 | 0.118* | |
H8BB | −0.1096 | 0.4188 | 0.2970 | 0.118* | |
H8BC | −0.0523 | 0.3886 | 0.2359 | 0.118* | |
C9B | 0.1719 (5) | 0.5645 (5) | 0.2862 (3) | 0.0637 (16) | |
H9BA | 0.1573 | 0.6176 | 0.2602 | 0.096* | |
H9BB | 0.1747 | 0.5059 | 0.2525 | 0.096* | |
H9BC | 0.2471 | 0.6062 | 0.3217 | 0.096* | |
C10B | 0.1994 (5) | 0.4048 (4) | 0.5582 (3) | 0.0537 (14) | |
H10B | 0.2425 | 0.4893 | 0.5757 | 0.064* | |
C11B | 0.2786 (6) | 0.3564 (9) | 0.5861 (4) | 0.124 (4) | |
H11A | 0.3493 | 0.3872 | 0.5671 | 0.185* | |
H11B | 0.2368 | 0.2733 | 0.5710 | 0.185* | |
H11C | 0.3012 | 0.3773 | 0.6385 | 0.185* | |
C12B | 0.0944 (6) | 0.3580 (8) | 0.5893 (3) | 0.093 (3) | |
H12A | 0.1198 | 0.3751 | 0.6416 | 0.140* | |
H12B | 0.0499 | 0.2753 | 0.5719 | 0.140* | |
H12C | 0.0442 | 0.3928 | 0.5748 | 0.140* | |
C13B | 0.2586 (3) | 0.6349 (4) | 0.5107 (2) | 0.0300 (9) | |
H13B | 0.3228 | 0.6203 | 0.5070 | 0.036* | |
C14B | 0.2817 (3) | 0.7428 (4) | 0.5567 (2) | 0.0285 (9) | |
C15B | 0.3963 (3) | 0.8319 (3) | 0.5849 (2) | 0.0255 (9) | |
C16B | 0.4137 (4) | 0.9304 (4) | 0.6290 (2) | 0.0358 (10) | |
H16B | 0.4913 | 0.9910 | 0.6475 | 0.043* | |
C17B | 0.3193 (4) | 0.9413 (5) | 0.6464 (3) | 0.0498 (13) | |
H17B | 0.3319 | 1.0087 | 0.6765 | 0.060* | |
C18B | 0.2073 (4) | 0.8532 (5) | 0.6193 (3) | 0.0522 (14) | |
H18B | 0.1424 | 0.8598 | 0.6314 | 0.063* | |
C19B | 0.1877 (4) | 0.7551 (4) | 0.5748 (2) | 0.0408 (11) | |
H19B | 0.1096 | 0.6956 | 0.5562 | 0.049* | |
C20B | 0.5325 (4) | 0.7150 (3) | 0.6169 (2) | 0.0303 (9) | |
C21B | 0.5863 (4) | 0.6517 (4) | 0.5954 (3) | 0.0472 (12) | |
H21B | 0.6147 | 0.6601 | 0.5530 | 0.057* | |
C22B | 0.5986 (5) | 0.5763 (5) | 0.6355 (3) | 0.0583 (15) | |
H22B | 0.6360 | 0.5335 | 0.6206 | 0.070* | |
C23B | 0.5574 (5) | 0.5629 (4) | 0.6964 (3) | 0.0538 (14) | |
H23B | 0.5659 | 0.5107 | 0.7234 | 0.065* | |
C24B | 0.5036 (4) | 0.6251 (4) | 0.7184 (3) | 0.0441 (12) | |
H24B | 0.4752 | 0.6157 | 0.7607 | 0.053* | |
C25B | 0.4908 (4) | 0.7011 (4) | 0.6794 (2) | 0.0335 (10) | |
H25B | 0.4537 | 0.7438 | 0.6949 | 0.040* | |
C26B | 0.6515 (3) | 0.9531 (3) | 0.6079 (2) | 0.0259 (9) | |
C27B | 0.6739 (4) | 1.0461 (4) | 0.5752 (2) | 0.0360 (10) | |
H27B | 0.6222 | 1.0376 | 0.5318 | 0.043* | |
C28B | 0.7708 (4) | 1.1509 (4) | 0.6056 (2) | 0.0392 (11) | |
H28B | 0.7845 | 1.2144 | 0.5836 | 0.047* | |
C29B | 0.8472 (4) | 1.1626 (4) | 0.6678 (2) | 0.0376 (11) | |
H29B | 0.9138 | 1.2343 | 0.6886 | 0.045* | |
C30B | 0.8276 (4) | 1.0710 (4) | 0.7001 (2) | 0.0380 (11) | |
H30B | 0.8812 | 1.0795 | 0.7426 | 0.046* | |
C31B | 0.7295 (4) | 0.9662 (4) | 0.6705 (2) | 0.0324 (10) | |
H31B | 0.7157 | 0.9034 | 0.6932 | 0.039* | |
Cl4 | 0.0094 (7) | −0.0310 (5) | 0.4177 (3) | 0.125 (2) | 0.50 |
Cl3 | −0.0785 (7) | 0.0091 (5) | 0.5291 (5) | 0.152 (3) | 0.50 |
Cl2 | 0.1757 (5) | 0.0690 (5) | 0.5517 (5) | 0.196 (4) | 0.50 |
C32 | 0.0374 (12) | −0.0182 (11) | 0.5187 (8) | 0.073 (4) | 0.50 |
H32 | 0.0202 | −0.0946 | 0.5297 | 0.087* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Au1A | 0.03151 (9) | 0.03684 (10) | 0.02132 (9) | 0.01715 (8) | 0.00154 (7) | −0.00024 (7) |
Cl1A | 0.0554 (7) | 0.0701 (8) | 0.0226 (6) | 0.0421 (7) | −0.0012 (5) | −0.0063 (5) |
P1A | 0.0270 (5) | 0.0312 (6) | 0.0202 (5) | 0.0126 (5) | 0.0029 (4) | 0.0010 (4) |
N1A | 0.040 (2) | 0.040 (2) | 0.041 (2) | 0.0153 (19) | 0.0033 (18) | 0.0086 (19) |
C1A | 0.033 (2) | 0.040 (3) | 0.037 (3) | 0.019 (2) | 0.001 (2) | 0.008 (2) |
C2A | 0.036 (2) | 0.043 (3) | 0.031 (2) | 0.018 (2) | 0.0076 (19) | 0.013 (2) |
C3A | 0.047 (3) | 0.051 (3) | 0.033 (3) | 0.020 (2) | 0.000 (2) | 0.014 (2) |
C4A | 0.048 (3) | 0.066 (4) | 0.052 (3) | 0.035 (3) | −0.006 (3) | 0.010 (3) |
C5A | 0.046 (3) | 0.067 (4) | 0.058 (4) | 0.038 (3) | 0.008 (3) | 0.002 (3) |
C6A | 0.046 (3) | 0.066 (4) | 0.041 (3) | 0.032 (3) | −0.001 (2) | −0.005 (3) |
C7A | 0.051 (3) | 0.102 (5) | 0.029 (3) | 0.040 (3) | 0.012 (2) | 0.018 (3) |
C8A | 0.112 (6) | 0.069 (5) | 0.141 (7) | 0.025 (4) | 0.089 (6) | −0.007 (5) |
C9A | 0.109 (6) | 0.065 (4) | 0.125 (7) | 0.030 (4) | 0.064 (5) | −0.008 (4) |
C10A | 0.078 (5) | 0.143 (7) | 0.056 (4) | 0.079 (5) | −0.006 (3) | −0.026 (4) |
C11A | 0.185 (11) | 0.134 (9) | 0.090 (7) | −0.037 (8) | 0.057 (7) | −0.044 (6) |
C12A | 0.145 (8) | 0.095 (6) | 0.063 (5) | 0.053 (5) | 0.036 (5) | 0.022 (4) |
C13A | 0.050 (3) | 0.038 (3) | 0.024 (2) | 0.025 (2) | 0.012 (2) | 0.0074 (19) |
C14A | 0.029 (2) | 0.037 (2) | 0.021 (2) | 0.0189 (19) | 0.0047 (17) | 0.0045 (18) |
C15A | 0.028 (2) | 0.034 (2) | 0.019 (2) | 0.0159 (18) | 0.0058 (16) | 0.0006 (17) |
C16A | 0.029 (2) | 0.035 (2) | 0.029 (2) | 0.0179 (19) | 0.0021 (18) | 0.0051 (19) |
C17A | 0.023 (2) | 0.040 (3) | 0.040 (3) | 0.013 (2) | −0.0037 (19) | −0.002 (2) |
C18A | 0.031 (2) | 0.034 (3) | 0.048 (3) | 0.008 (2) | 0.003 (2) | 0.001 (2) |
C19A | 0.041 (3) | 0.031 (2) | 0.036 (3) | 0.018 (2) | 0.007 (2) | 0.0038 (19) |
C20A | 0.028 (2) | 0.032 (2) | 0.026 (2) | 0.0142 (19) | 0.0024 (17) | 0.0091 (18) |
C21A | 0.032 (2) | 0.040 (3) | 0.034 (3) | 0.013 (2) | 0.0037 (19) | 0.005 (2) |
C22A | 0.027 (2) | 0.054 (3) | 0.046 (3) | 0.012 (2) | 0.008 (2) | 0.015 (2) |
C23A | 0.040 (3) | 0.060 (3) | 0.047 (3) | 0.032 (3) | 0.023 (2) | 0.025 (3) |
C24A | 0.041 (3) | 0.043 (3) | 0.034 (3) | 0.024 (2) | 0.012 (2) | 0.008 (2) |
C25A | 0.028 (2) | 0.038 (2) | 0.029 (2) | 0.0146 (19) | 0.0076 (18) | 0.0051 (19) |
C26A | 0.029 (2) | 0.033 (2) | 0.022 (2) | 0.0144 (19) | 0.0015 (17) | 0.0008 (17) |
C27A | 0.063 (3) | 0.059 (3) | 0.030 (3) | 0.038 (3) | 0.017 (2) | 0.009 (2) |
C28A | 0.098 (5) | 0.073 (4) | 0.045 (3) | 0.067 (4) | 0.024 (3) | 0.018 (3) |
C29A | 0.084 (4) | 0.052 (3) | 0.039 (3) | 0.047 (3) | 0.008 (3) | 0.010 (2) |
C30A | 0.063 (3) | 0.049 (3) | 0.032 (3) | 0.030 (3) | 0.012 (2) | 0.010 (2) |
C31A | 0.057 (3) | 0.046 (3) | 0.025 (2) | 0.031 (2) | 0.009 (2) | 0.005 (2) |
Au1B | 0.03466 (10) | 0.03069 (9) | 0.02350 (9) | 0.01670 (8) | 0.00744 (7) | 0.00507 (7) |
Cl1B | 0.0784 (9) | 0.0528 (7) | 0.0262 (6) | 0.0337 (7) | 0.0169 (6) | 0.0079 (5) |
P1B | 0.0259 (5) | 0.0279 (5) | 0.0226 (5) | 0.0135 (4) | 0.0054 (4) | 0.0060 (4) |
N1B | 0.026 (2) | 0.055 (3) | 0.038 (2) | 0.0140 (19) | 0.0013 (17) | −0.0079 (19) |
C1B | 0.021 (2) | 0.039 (3) | 0.038 (3) | 0.0006 (19) | 0.0084 (19) | −0.003 (2) |
C2B | 0.024 (2) | 0.043 (3) | 0.034 (3) | 0.006 (2) | 0.0034 (19) | −0.001 (2) |
C3B | 0.034 (3) | 0.041 (3) | 0.033 (3) | 0.004 (2) | 0.008 (2) | −0.001 (2) |
C4B | 0.056 (3) | 0.037 (3) | 0.043 (3) | 0.002 (2) | 0.013 (3) | −0.003 (2) |
C5B | 0.060 (3) | 0.040 (3) | 0.043 (3) | 0.005 (3) | 0.014 (3) | 0.010 (2) |
C6B | 0.039 (3) | 0.040 (3) | 0.031 (3) | −0.002 (2) | 0.009 (2) | −0.001 (2) |
C7B | 0.037 (3) | 0.051 (3) | 0.039 (3) | 0.017 (2) | −0.003 (2) | −0.008 (2) |
C8B | 0.055 (4) | 0.072 (4) | 0.083 (5) | 0.028 (3) | −0.029 (3) | −0.009 (4) |
C9B | 0.069 (4) | 0.068 (4) | 0.065 (4) | 0.036 (3) | 0.023 (3) | 0.023 (3) |
C10B | 0.064 (4) | 0.037 (3) | 0.034 (3) | 0.003 (3) | 0.009 (2) | 0.006 (2) |
C11B | 0.068 (5) | 0.260 (12) | 0.049 (4) | 0.099 (6) | −0.007 (3) | −0.011 (5) |
C12B | 0.077 (5) | 0.190 (8) | 0.050 (4) | 0.086 (5) | 0.031 (3) | 0.040 (5) |
C13B | 0.023 (2) | 0.036 (2) | 0.027 (2) | 0.0100 (19) | 0.0042 (17) | 0.0094 (18) |
C14B | 0.028 (2) | 0.036 (2) | 0.024 (2) | 0.0171 (19) | 0.0051 (17) | 0.0071 (18) |
C15B | 0.025 (2) | 0.031 (2) | 0.022 (2) | 0.0135 (18) | 0.0048 (16) | 0.0084 (17) |
C16B | 0.032 (2) | 0.035 (2) | 0.036 (3) | 0.014 (2) | 0.0080 (19) | 0.001 (2) |
C17B | 0.046 (3) | 0.054 (3) | 0.050 (3) | 0.027 (3) | 0.013 (2) | −0.006 (3) |
C18B | 0.035 (3) | 0.067 (4) | 0.057 (3) | 0.028 (3) | 0.015 (2) | −0.004 (3) |
C19B | 0.026 (2) | 0.052 (3) | 0.040 (3) | 0.017 (2) | 0.005 (2) | 0.006 (2) |
C20B | 0.029 (2) | 0.028 (2) | 0.032 (2) | 0.0123 (18) | 0.0034 (18) | 0.0096 (18) |
C21B | 0.051 (3) | 0.057 (3) | 0.053 (3) | 0.037 (3) | 0.019 (2) | 0.023 (3) |
C22B | 0.065 (4) | 0.058 (3) | 0.079 (4) | 0.046 (3) | 0.022 (3) | 0.031 (3) |
C23B | 0.053 (3) | 0.046 (3) | 0.065 (4) | 0.023 (3) | 0.006 (3) | 0.030 (3) |
C24B | 0.046 (3) | 0.038 (3) | 0.037 (3) | 0.009 (2) | 0.004 (2) | 0.015 (2) |
C25B | 0.033 (2) | 0.030 (2) | 0.034 (2) | 0.0118 (19) | 0.0065 (19) | 0.0083 (19) |
C26B | 0.022 (2) | 0.030 (2) | 0.025 (2) | 0.0108 (17) | 0.0065 (16) | 0.0069 (17) |
C27B | 0.030 (2) | 0.038 (3) | 0.029 (2) | 0.010 (2) | −0.0046 (18) | 0.008 (2) |
C28B | 0.037 (3) | 0.035 (3) | 0.038 (3) | 0.010 (2) | 0.003 (2) | 0.013 (2) |
C29B | 0.027 (2) | 0.036 (3) | 0.037 (3) | 0.004 (2) | 0.0041 (19) | 0.006 (2) |
C30B | 0.033 (2) | 0.043 (3) | 0.028 (2) | 0.011 (2) | −0.0031 (19) | 0.008 (2) |
C31B | 0.031 (2) | 0.036 (2) | 0.029 (2) | 0.013 (2) | 0.0077 (18) | 0.0131 (19) |
Cl4 | 0.197 (7) | 0.065 (3) | 0.110 (4) | 0.052 (4) | 0.059 (4) | 0.022 (3) |
Cl3 | 0.184 (8) | 0.077 (4) | 0.261 (9) | 0.082 (5) | 0.144 (7) | 0.060 (6) |
Cl2 | 0.116 (4) | 0.081 (3) | 0.322 (10) | 0.014 (3) | −0.059 (5) | 0.076 (5) |
C32 | 0.079 (9) | 0.068 (9) | 0.101 (11) | 0.045 (7) | 0.049 (9) | 0.044 (8) |
Au1A—P1A | 2.2354 (10) | P1B—C26B | 1.811 (4) |
Au1A—Cl1A | 2.2783 (11) | P1B—C20B | 1.814 (4) |
P1A—C26A | 1.807 (4) | P1B—C15B | 1.828 (4) |
P1A—C20A | 1.824 (4) | N1B—C13B | 1.258 (5) |
P1A—C15A | 1.835 (4) | N1B—C1B | 1.435 (6) |
N1A—C13A | 1.236 (6) | C1B—C2B | 1.404 (6) |
N1A—C1A | 1.442 (6) | C1B—C6B | 1.411 (7) |
C1A—C2A | 1.399 (6) | C2B—C3B | 1.389 (7) |
C1A—C6A | 1.400 (7) | C2B—C7B | 1.514 (7) |
C2A—C3A | 1.383 (6) | C3B—C4B | 1.369 (7) |
C2A—C7A | 1.534 (7) | C3B—H3B | 0.9500 |
C3A—C4A | 1.377 (7) | C4B—C5B | 1.388 (7) |
C3A—H3A | 0.9500 | C4B—H4B | 0.9500 |
C4A—C5A | 1.373 (7) | C5B—C6B | 1.395 (7) |
C4A—H4A | 0.9500 | C5B—H5B | 0.9500 |
C5A—C6A | 1.387 (7) | C6B—C10B | 1.520 (7) |
C5A—H5A | 0.9500 | C7B—C9B | 1.520 (7) |
C6A—C10A | 1.558 (8) | C7B—C8B | 1.538 (7) |
C7A—C8A | 1.476 (8) | C7B—H7B | 1.0000 |
C7A—C9A | 1.518 (9) | C8B—H8BA | 0.9800 |
C7A—H7A | 1.0000 | C8B—H8BB | 0.9800 |
C8A—H8AA | 0.9800 | C8B—H8BC | 0.9800 |
C8A—H8AB | 0.9800 | C9B—H9BA | 0.9800 |
C8A—H8AC | 0.9800 | C9B—H9BB | 0.9800 |
C9A—H9AA | 0.9800 | C9B—H9BC | 0.9800 |
C9A—H9AB | 0.9800 | C10B—C12B | 1.490 (8) |
C9A—H9AC | 0.9800 | C10B—C11B | 1.504 (9) |
C10A—C11A | 1.460 (11) | C10B—H10B | 1.0000 |
C10A—C12A | 1.499 (10) | C11B—H11A | 0.9800 |
C10A—H10A | 1.0000 | C11B—H11B | 0.9800 |
C11A—H11D | 0.9800 | C11B—H11C | 0.9800 |
C11A—H11E | 0.9800 | C12B—H12A | 0.9800 |
C11A—H11F | 0.9800 | C12B—H12B | 0.9800 |
C12A—H12D | 0.9800 | C12B—H12C | 0.9800 |
C12A—H12E | 0.9800 | C13B—C14B | 1.487 (6) |
C12A—H12F | 0.9800 | C13B—H13B | 0.9500 |
C13A—C14A | 1.497 (6) | C14B—C19B | 1.396 (6) |
C13A—H13A | 0.9500 | C14B—C15B | 1.404 (6) |
C14A—C19A | 1.385 (6) | C15B—C16B | 1.392 (6) |
C14A—C15A | 1.409 (6) | C16B—C17B | 1.388 (6) |
C15A—C16A | 1.393 (5) | C16B—H16B | 0.9500 |
C16A—C17A | 1.390 (6) | C17B—C18B | 1.376 (7) |
C16A—H16A | 0.9500 | C17B—H17B | 0.9500 |
C17A—C18A | 1.375 (6) | C18B—C19B | 1.382 (7) |
C17A—H17A | 0.9500 | C18B—H18B | 0.9500 |
C18A—C19A | 1.387 (6) | C19B—H19B | 0.9500 |
C18A—H18A | 0.9500 | C20B—C21B | 1.385 (6) |
C19A—H19A | 0.9500 | C20B—C25B | 1.401 (6) |
C20A—C21A | 1.378 (6) | C21B—C22B | 1.386 (7) |
C20A—C25A | 1.383 (6) | C21B—H21B | 0.9500 |
C21A—C22A | 1.385 (6) | C22B—C23B | 1.369 (8) |
C21A—H21A | 0.9500 | C22B—H22B | 0.9500 |
C22A—C23A | 1.375 (7) | C23B—C24B | 1.376 (7) |
C22A—H22A | 0.9500 | C23B—H23B | 0.9500 |
C23A—C24A | 1.385 (6) | C24B—C25B | 1.382 (6) |
C23A—H23A | 0.9500 | C24B—H24B | 0.9500 |
C24A—C25A | 1.386 (6) | C25B—H25B | 0.9500 |
C24A—H24A | 0.9500 | C26B—C31B | 1.391 (6) |
C25A—H25A | 0.9500 | C26B—C27B | 1.394 (6) |
C26A—C27A | 1.384 (6) | C27B—C28B | 1.385 (6) |
C26A—C31A | 1.393 (6) | C27B—H27B | 0.9500 |
C27A—C28A | 1.377 (7) | C28B—C29B | 1.380 (6) |
C27A—H27A | 0.9500 | C28B—H28B | 0.9500 |
C28A—C29A | 1.375 (7) | C29B—C30B | 1.378 (6) |
C28A—H28A | 0.9500 | C29B—H29B | 0.9500 |
C29A—C30A | 1.373 (7) | C30B—C31B | 1.390 (6) |
C29A—H29A | 0.9500 | C30B—H30B | 0.9500 |
C30A—C31A | 1.383 (6) | C31B—H31B | 0.9500 |
C30A—H30A | 0.9500 | Cl4—C32 | 1.903 (16) |
C31A—H31A | 0.9500 | Cl3—C32 | 1.739 (14) |
Au1B—P1B | 2.2267 (10) | Cl2—C32 | 1.621 (15) |
Au1B—Cl1B | 2.2707 (11) | C32—H32 | 1.0000 |
P1A—Au1A—Cl1A | 177.20 (4) | C20B—P1B—C15B | 104.38 (19) |
C26A—P1A—C20A | 105.25 (19) | C26B—P1B—Au1B | 110.11 (13) |
C26A—P1A—C15A | 105.82 (19) | C20B—P1B—Au1B | 115.53 (15) |
C20A—P1A—C15A | 105.36 (18) | C15B—P1B—Au1B | 113.46 (13) |
C26A—P1A—Au1A | 110.70 (13) | C13B—N1B—C1B | 118.3 (4) |
C20A—P1A—Au1A | 116.83 (13) | C2B—C1B—C6B | 121.7 (4) |
C15A—P1A—Au1A | 112.07 (13) | C2B—C1B—N1B | 118.4 (5) |
C13A—N1A—C1A | 117.9 (4) | C6B—C1B—N1B | 119.8 (4) |
C2A—C1A—C6A | 122.2 (4) | C3B—C2B—C1B | 118.3 (5) |
C2A—C1A—N1A | 118.8 (4) | C3B—C2B—C7B | 120.6 (4) |
C6A—C1A—N1A | 118.9 (4) | C1B—C2B—C7B | 121.1 (4) |
C3A—C2A—C1A | 117.3 (4) | C4B—C3B—C2B | 121.5 (5) |
C3A—C2A—C7A | 120.9 (4) | C4B—C3B—H3B | 119.3 |
C1A—C2A—C7A | 121.9 (4) | C2B—C3B—H3B | 119.3 |
C4A—C3A—C2A | 121.4 (5) | C3B—C4B—C5B | 119.7 (5) |
C4A—C3A—H3A | 119.3 | C3B—C4B—H4B | 120.2 |
C2A—C3A—H3A | 119.3 | C5B—C4B—H4B | 120.2 |
C5A—C4A—C3A | 120.4 (5) | C4B—C5B—C6B | 121.9 (5) |
C5A—C4A—H4A | 119.8 | C4B—C5B—H5B | 119.0 |
C3A—C4A—H4A | 119.8 | C6B—C5B—H5B | 119.0 |
C4A—C5A—C6A | 120.9 (5) | C5B—C6B—C1B | 117.0 (4) |
C4A—C5A—H5A | 119.6 | C5B—C6B—C10B | 119.8 (5) |
C6A—C5A—H5A | 119.6 | C1B—C6B—C10B | 123.1 (5) |
C5A—C6A—C1A | 117.7 (5) | C2B—C7B—C9B | 109.8 (4) |
C5A—C6A—C10A | 121.4 (5) | C2B—C7B—C8B | 112.1 (4) |
C1A—C6A—C10A | 120.9 (4) | C9B—C7B—C8B | 111.4 (5) |
C8A—C7A—C9A | 111.3 (5) | C2B—C7B—H7B | 107.8 |
C8A—C7A—C2A | 111.7 (5) | C9B—C7B—H7B | 107.8 |
C9A—C7A—C2A | 114.4 (5) | C8B—C7B—H7B | 107.8 |
C8A—C7A—H7A | 106.3 | C7B—C8B—H8BA | 109.5 |
C9A—C7A—H7A | 106.3 | C7B—C8B—H8BB | 109.5 |
C2A—C7A—H7A | 106.3 | H8BA—C8B—H8BB | 109.5 |
C7A—C8A—H8AA | 109.5 | C7B—C8B—H8BC | 109.5 |
C7A—C8A—H8AB | 109.5 | H8BA—C8B—H8BC | 109.5 |
H8AA—C8A—H8AB | 109.5 | H8BB—C8B—H8BC | 109.5 |
C7A—C8A—H8AC | 109.5 | C7B—C9B—H9BA | 109.5 |
H8AA—C8A—H8AC | 109.5 | C7B—C9B—H9BB | 109.5 |
H8AB—C8A—H8AC | 109.5 | H9BA—C9B—H9BB | 109.5 |
C7A—C9A—H9AA | 109.5 | C7B—C9B—H9BC | 109.5 |
C7A—C9A—H9AB | 109.5 | H9BA—C9B—H9BC | 109.5 |
H9AA—C9A—H9AB | 109.5 | H9BB—C9B—H9BC | 109.5 |
C7A—C9A—H9AC | 109.5 | C12B—C10B—C11B | 107.9 (5) |
H9AA—C9A—H9AC | 109.5 | C12B—C10B—C6B | 110.2 (5) |
H9AB—C9A—H9AC | 109.5 | C11B—C10B—C6B | 114.0 (5) |
C11A—C10A—C12A | 111.7 (7) | C12B—C10B—H10B | 108.2 |
C11A—C10A—C6A | 108.8 (7) | C11B—C10B—H10B | 108.2 |
C12A—C10A—C6A | 114.0 (5) | C6B—C10B—H10B | 108.2 |
C11A—C10A—H10A | 107.4 | C10B—C11B—H11A | 109.5 |
C12A—C10A—H10A | 107.4 | C10B—C11B—H11B | 109.5 |
C6A—C10A—H10A | 107.4 | H11A—C11B—H11B | 109.5 |
C10A—C11A—H11D | 109.5 | C10B—C11B—H11C | 109.5 |
C10A—C11A—H11E | 109.5 | H11A—C11B—H11C | 109.5 |
H11D—C11A—H11E | 109.5 | H11B—C11B—H11C | 109.5 |
C10A—C11A—H11F | 109.5 | C10B—C12B—H12A | 109.5 |
H11D—C11A—H11F | 109.5 | C10B—C12B—H12B | 109.5 |
H11E—C11A—H11F | 109.5 | H12A—C12B—H12B | 109.5 |
C10A—C12A—H12D | 109.5 | C10B—C12B—H12C | 109.5 |
C10A—C12A—H12E | 109.5 | H12A—C12B—H12C | 109.5 |
H12D—C12A—H12E | 109.5 | H12B—C12B—H12C | 109.5 |
C10A—C12A—H12F | 109.5 | N1B—C13B—C14B | 121.9 (4) |
H12D—C12A—H12F | 109.5 | N1B—C13B—H13B | 119.1 |
H12E—C12A—H12F | 109.5 | C14B—C13B—H13B | 119.1 |
N1A—C13A—C14A | 122.4 (4) | C19B—C14B—C15B | 118.7 (4) |
N1A—C13A—H13A | 118.8 | C19B—C14B—C13B | 119.6 (4) |
C14A—C13A—H13A | 118.8 | C15B—C14B—C13B | 121.7 (4) |
C19A—C14A—C15A | 119.1 (4) | C16B—C15B—C14B | 119.7 (4) |
C19A—C14A—C13A | 120.5 (4) | C16B—C15B—P1B | 119.6 (3) |
C15A—C14A—C13A | 120.4 (4) | C14B—C15B—P1B | 120.6 (3) |
C16A—C15A—C14A | 119.5 (4) | C17B—C16B—C15B | 120.9 (4) |
C16A—C15A—P1A | 119.3 (3) | C17B—C16B—H16B | 119.6 |
C14A—C15A—P1A | 121.1 (3) | C15B—C16B—H16B | 119.6 |
C17A—C16A—C15A | 120.0 (4) | C18B—C17B—C16B | 119.2 (5) |
C17A—C16A—H16A | 120.0 | C18B—C17B—H17B | 120.4 |
C15A—C16A—H16A | 120.0 | C16B—C17B—H17B | 120.4 |
C18A—C17A—C16A | 120.6 (4) | C17B—C18B—C19B | 120.9 (4) |
C18A—C17A—H17A | 119.7 | C17B—C18B—H18B | 119.5 |
C16A—C17A—H17A | 119.7 | C19B—C18B—H18B | 119.5 |
C17A—C18A—C19A | 119.7 (4) | C18B—C19B—C14B | 120.6 (4) |
C17A—C18A—H18A | 120.1 | C18B—C19B—H19B | 119.7 |
C19A—C18A—H18A | 120.1 | C14B—C19B—H19B | 119.7 |
C14A—C19A—C18A | 121.1 (4) | C21B—C20B—C25B | 119.0 (4) |
C14A—C19A—H19A | 119.5 | C21B—C20B—P1B | 119.6 (3) |
C18A—C19A—H19A | 119.5 | C25B—C20B—P1B | 121.4 (3) |
C21A—C20A—C25A | 120.0 (4) | C20B—C21B—C22B | 120.1 (5) |
C21A—C20A—P1A | 119.4 (3) | C20B—C21B—H21B | 119.9 |
C25A—C20A—P1A | 120.4 (3) | C22B—C21B—H21B | 119.9 |
C20A—C21A—C22A | 119.7 (4) | C23B—C22B—C21B | 120.6 (5) |
C20A—C21A—H21A | 120.1 | C23B—C22B—H22B | 119.7 |
C22A—C21A—H21A | 120.1 | C21B—C22B—H22B | 119.7 |
C23A—C22A—C21A | 120.4 (4) | C22B—C23B—C24B | 120.0 (5) |
C23A—C22A—H22A | 119.8 | C22B—C23B—H23B | 120.0 |
C21A—C22A—H22A | 119.8 | C24B—C23B—H23B | 120.0 |
C22A—C23A—C24A | 120.1 (4) | C23B—C24B—C25B | 120.4 (5) |
C22A—C23A—H23A | 120.0 | C23B—C24B—H24B | 119.8 |
C24A—C23A—H23A | 120.0 | C25B—C24B—H24B | 119.8 |
C23A—C24A—C25A | 119.5 (4) | C24B—C25B—C20B | 120.0 (4) |
C23A—C24A—H24A | 120.3 | C24B—C25B—H25B | 120.0 |
C25A—C24A—H24A | 120.3 | C20B—C25B—H25B | 120.0 |
C20A—C25A—C24A | 120.2 (4) | C31B—C26B—C27B | 119.0 (4) |
C20A—C25A—H25A | 119.9 | C31B—C26B—P1B | 122.2 (3) |
C24A—C25A—H25A | 119.9 | C27B—C26B—P1B | 118.8 (3) |
C27A—C26A—C31A | 118.5 (4) | C28B—C27B—C26B | 120.6 (4) |
C27A—C26A—P1A | 119.4 (3) | C28B—C27B—H27B | 119.7 |
C31A—C26A—P1A | 122.1 (3) | C26B—C27B—H27B | 119.7 |
C28A—C27A—C26A | 121.1 (4) | C29B—C28B—C27B | 119.7 (4) |
C28A—C27A—H27A | 119.5 | C29B—C28B—H28B | 120.2 |
C26A—C27A—H27A | 119.5 | C27B—C28B—H28B | 120.2 |
C29A—C28A—C27A | 119.6 (5) | C30B—C29B—C28B | 120.5 (4) |
C29A—C28A—H28A | 120.2 | C30B—C29B—H29B | 119.7 |
C27A—C28A—H28A | 120.2 | C28B—C29B—H29B | 119.7 |
C30A—C29A—C28A | 120.6 (5) | C29B—C30B—C31B | 120.0 (4) |
C30A—C29A—H29A | 119.7 | C29B—C30B—H30B | 120.0 |
C28A—C29A—H29A | 119.7 | C31B—C30B—H30B | 120.0 |
C29A—C30A—C31A | 119.8 (5) | C30B—C31B—C26B | 120.2 (4) |
C29A—C30A—H30A | 120.1 | C30B—C31B—H31B | 119.9 |
C31A—C30A—H30A | 120.1 | C26B—C31B—H31B | 119.9 |
C30A—C31A—C26A | 120.4 (4) | Cl2—C32—Cl3 | 125.5 (10) |
C30A—C31A—H31A | 119.8 | Cl2—C32—Cl4 | 107.2 (9) |
C26A—C31A—H31A | 119.8 | Cl3—C32—Cl4 | 95.9 (7) |
P1B—Au1B—Cl1B | 178.54 (4) | Cl2—C32—H32 | 108.9 |
C26B—P1B—C20B | 106.29 (19) | Cl3—C32—H32 | 108.9 |
C26B—P1B—C15B | 106.40 (18) | Cl4—C32—H32 | 108.9 |
C13A—N1A—C1A—C2A | −90.8 (5) | C13B—N1B—C1B—C2B | −119.9 (5) |
C13A—N1A—C1A—C6A | 93.0 (6) | C13B—N1B—C1B—C6B | 65.0 (6) |
C6A—C1A—C2A—C3A | 3.6 (7) | C6B—C1B—C2B—C3B | −2.1 (6) |
N1A—C1A—C2A—C3A | −172.4 (4) | N1B—C1B—C2B—C3B | −177.1 (4) |
C6A—C1A—C2A—C7A | −176.1 (5) | C6B—C1B—C2B—C7B | −180.0 (4) |
N1A—C1A—C2A—C7A | 7.9 (7) | N1B—C1B—C2B—C7B | 5.0 (6) |
C1A—C2A—C3A—C4A | −1.8 (7) | C1B—C2B—C3B—C4B | 0.7 (7) |
C7A—C2A—C3A—C4A | 177.8 (5) | C7B—C2B—C3B—C4B | 178.6 (4) |
C2A—C3A—C4A—C5A | −0.5 (8) | C2B—C3B—C4B—C5B | 0.3 (7) |
C3A—C4A—C5A—C6A | 1.3 (9) | C3B—C4B—C5B—C6B | −0.1 (8) |
C4A—C5A—C6A—C1A | 0.4 (8) | C4B—C5B—C6B—C1B | −1.2 (7) |
C4A—C5A—C6A—C10A | −178.5 (6) | C4B—C5B—C6B—C10B | 175.4 (5) |
C2A—C1A—C6A—C5A | −2.9 (8) | C2B—C1B—C6B—C5B | 2.3 (7) |
N1A—C1A—C6A—C5A | 173.1 (5) | N1B—C1B—C6B—C5B | 177.2 (4) |
C2A—C1A—C6A—C10A | 176.0 (5) | C2B—C1B—C6B—C10B | −174.1 (4) |
N1A—C1A—C6A—C10A | −8.0 (8) | N1B—C1B—C6B—C10B | 0.8 (7) |
C3A—C2A—C7A—C8A | 93.8 (7) | C3B—C2B—C7B—C9B | −75.9 (5) |
C1A—C2A—C7A—C8A | −86.6 (7) | C1B—C2B—C7B—C9B | 101.9 (5) |
C3A—C2A—C7A—C9A | −33.8 (8) | C3B—C2B—C7B—C8B | 48.4 (6) |
C1A—C2A—C7A—C9A | 145.9 (6) | C1B—C2B—C7B—C8B | −133.7 (5) |
C5A—C6A—C10A—C11A | −95.5 (9) | C5B—C6B—C10B—C12B | −85.3 (7) |
C1A—C6A—C10A—C11A | 85.6 (9) | C1B—C6B—C10B—C12B | 91.0 (6) |
C5A—C6A—C10A—C12A | 29.8 (10) | C5B—C6B—C10B—C11B | 36.2 (7) |
C1A—C6A—C10A—C12A | −149.1 (6) | C1B—C6B—C10B—C11B | −147.5 (6) |
C1A—N1A—C13A—C14A | −179.9 (4) | C1B—N1B—C13B—C14B | −174.4 (4) |
N1A—C13A—C14A—C19A | −3.6 (6) | N1B—C13B—C14B—C19B | 13.4 (6) |
N1A—C13A—C14A—C15A | 176.0 (4) | N1B—C13B—C14B—C15B | −168.9 (4) |
C19A—C14A—C15A—C16A | 1.2 (6) | C19B—C14B—C15B—C16B | −0.9 (6) |
C13A—C14A—C15A—C16A | −178.5 (4) | C13B—C14B—C15B—C16B | −178.6 (4) |
C19A—C14A—C15A—P1A | −175.3 (3) | C19B—C14B—C15B—P1B | 177.5 (3) |
C13A—C14A—C15A—P1A | 5.0 (5) | C13B—C14B—C15B—P1B | −0.2 (5) |
C26A—P1A—C15A—C16A | 4.0 (4) | C26B—P1B—C15B—C16B | −4.7 (4) |
C20A—P1A—C15A—C16A | 115.2 (3) | C20B—P1B—C15B—C16B | 107.5 (4) |
Au1A—P1A—C15A—C16A | −116.7 (3) | Au1B—P1B—C15B—C16B | −125.9 (3) |
C26A—P1A—C15A—C14A | −179.5 (3) | C26B—P1B—C15B—C14B | 176.9 (3) |
C20A—P1A—C15A—C14A | −68.3 (4) | C20B—P1B—C15B—C14B | −70.9 (4) |
Au1A—P1A—C15A—C14A | 59.8 (3) | Au1B—P1B—C15B—C14B | 55.7 (3) |
C14A—C15A—C16A—C17A | −0.9 (6) | C14B—C15B—C16B—C17B | 0.9 (7) |
P1A—C15A—C16A—C17A | 175.7 (3) | P1B—C15B—C16B—C17B | −177.5 (4) |
C15A—C16A—C17A—C18A | 0.0 (7) | C15B—C16B—C17B—C18B | −0.1 (8) |
C16A—C17A—C18A—C19A | 0.6 (7) | C16B—C17B—C18B—C19B | −0.7 (8) |
C15A—C14A—C19A—C18A | −0.6 (6) | C17B—C18B—C19B—C14B | 0.6 (8) |
C13A—C14A—C19A—C18A | 179.1 (4) | C15B—C14B—C19B—C18B | 0.2 (7) |
C17A—C18A—C19A—C14A | −0.3 (7) | C13B—C14B—C19B—C18B | 177.9 (4) |
C26A—P1A—C20A—C21A | −86.0 (4) | C26B—P1B—C20B—C21B | −92.6 (4) |
C15A—P1A—C20A—C21A | 162.4 (3) | C15B—P1B—C20B—C21B | 155.1 (4) |
Au1A—P1A—C20A—C21A | 37.2 (4) | Au1B—P1B—C20B—C21B | 29.8 (4) |
C26A—P1A—C20A—C25A | 90.8 (4) | C26B—P1B—C20B—C25B | 84.7 (4) |
C15A—P1A—C20A—C25A | −20.8 (4) | C15B—P1B—C20B—C25B | −27.6 (4) |
Au1A—P1A—C20A—C25A | −145.9 (3) | Au1B—P1B—C20B—C25B | −152.9 (3) |
C25A—C20A—C21A—C22A | −0.2 (7) | C25B—C20B—C21B—C22B | −0.2 (7) |
P1A—C20A—C21A—C22A | 176.6 (4) | P1B—C20B—C21B—C22B | 177.1 (4) |
C20A—C21A—C22A—C23A | 0.2 (7) | C20B—C21B—C22B—C23B | 0.4 (9) |
C21A—C22A—C23A—C24A | −0.3 (7) | C21B—C22B—C23B—C24B | −0.3 (9) |
C22A—C23A—C24A—C25A | 0.4 (7) | C22B—C23B—C24B—C25B | 0.1 (8) |
C21A—C20A—C25A—C24A | 0.3 (6) | C23B—C24B—C25B—C20B | 0.1 (7) |
P1A—C20A—C25A—C24A | −176.5 (3) | C21B—C20B—C25B—C24B | 0.0 (7) |
C23A—C24A—C25A—C20A | −0.4 (7) | P1B—C20B—C25B—C24B | −177.3 (3) |
C20A—P1A—C26A—C27A | 159.0 (4) | C20B—P1B—C26B—C31B | −5.3 (4) |
C15A—P1A—C26A—C27A | −89.7 (4) | C15B—P1B—C26B—C31B | 105.5 (4) |
Au1A—P1A—C26A—C27A | 31.9 (4) | Au1B—P1B—C26B—C31B | −131.2 (3) |
C20A—P1A—C26A—C31A | −20.9 (4) | C20B—P1B—C26B—C27B | 173.3 (3) |
C15A—P1A—C26A—C31A | 90.4 (4) | C15B—P1B—C26B—C27B | −75.9 (4) |
Au1A—P1A—C26A—C31A | −148.0 (3) | Au1B—P1B—C26B—C27B | 47.5 (4) |
C31A—C26A—C27A—C28A | −1.1 (7) | C31B—C26B—C27B—C28B | −1.6 (7) |
P1A—C26A—C27A—C28A | 178.9 (4) | P1B—C26B—C27B—C28B | 179.7 (4) |
C26A—C27A—C28A—C29A | 2.0 (9) | C26B—C27B—C28B—C29B | 1.5 (7) |
C27A—C28A—C29A—C30A | −1.3 (9) | C27B—C28B—C29B—C30B | −0.2 (7) |
C28A—C29A—C30A—C31A | −0.2 (8) | C28B—C29B—C30B—C31B | −0.9 (7) |
C29A—C30A—C31A—C26A | 1.1 (8) | C29B—C30B—C31B—C26B | 0.7 (7) |
C27A—C26A—C31A—C30A | −0.4 (7) | C27B—C26B—C31B—C30B | 0.6 (6) |
P1A—C26A—C31A—C30A | 179.5 (4) | P1B—C26B—C31B—C30B | 179.2 (3) |
Experimental details
Crystal data | |
Chemical formula | [AuCl(C31H32NP)]·0.25CHCl3 |
Mr | 711.81 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 13.0315 (3), 13.3638 (2), 19.3489 (5) |
α, β, γ (°) | 96.358 (2), 99.229 (1), 116.191 (1) |
V (Å3) | 2921.15 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 5.27 |
Crystal size (mm) | 0.21 × 0.18 × 0.12 |
Data collection | |
Diffractometer | Bruker APEXII 4K CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.404, 0.570 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 119407, 11945, 9894 |
Rint | 0.053 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.065, 1.09 |
No. of reflections | 11945 |
No. of parameters | 667 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.91, −1.54 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SAINT and XPREP (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 2012).
Acknowledgements
Mintek and Project AuTEK are acknowledged for funding this project. HC also thanks the late Professor J. R. Moss for fruitful discussions.
References
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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.
Studies of gold(I) complexes have been related to anti-arthritic (Shaw, 1999), anti-tumor (Barnard et al., 2004) and antimicrobial physiological activities (Nomiya et al., 2003). The treatment of diseases with gold complexes (called chrysotherapy) can be traced back to early times (Cowan, 1993). The mechanistic approach regarding the action of gold drugs is still a matter of interest and research, however they remain the most effective second line treatment for rheumatoid arthritis (Parish, 1992; Fricker, 1996). This led to the development of a gold complex called auranofin, which was found to be an experimental chrysotherapeutic agent and was clinically effective in the treatment of rheumatoid arthritis (Finkelstein et al., 1976). Our group has recently been involved in the development of novel Au(I) complexes with iminophosphine ligands and these have shown promising activity when evaluated against two oesophageal cancer cell lines (Chiririwa et al., 2013).
The structure of the title compound (Fig. 1) was determined to establish the coordination properties of the 2-(diphenylphosphanyl)benzylidene)- 2,6-diisopropylbenzenamine ligand with gold. The asymmetric unit consists of two crystallographically independent complex molecules. The Au—P bond distances of 2.2354 (10) and 2.2267 (10) Å agree well with reported values (Williams et al.., 2007; Chiririwa & Muller, 2012). The chloroform solvent molecule is disordered across an inversion centre.