Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039529/nc2053sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039529/nc2053Isup2.hkl |
CCDC reference: 660110
Key indicators
- Single-crystal X-ray study
- T = 165 K
- Mean (C-C) = 0.014 Å
- R factor = 0.038
- wR factor = 0.077
- Data-to-parameter ratio = 19.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.69 Ratio
Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Au1 - P1 .. 5.57 su PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 14 PLAT480_ALERT_4_C Long H...A H-Bond Reported H6A .. CL1 .. 3.12 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H15A .. CL2 .. 3.15 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H16A .. CL2 .. 3.00 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H19A .. CL1 .. 3.10 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.58 From the CIF: _reflns_number_total 4750 Count of symmetry unique reflns 2741 Completeness (_total/calc) 173.29% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2009 Fraction of Friedel pairs measured 0.733 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Gold catalysis is becoming increasingly important (Hashmi & Hutchings, 2006) and the use of chiral gold complexes for enantioselective catalysis is one of the latest hot topics (Hashmi, 2005). In this context detailed structural information about these gold complexes is of high importance. Thus we conducted a crystal structure analysis of the title compound, which was prepared in analogy to related compounds (King & Eisch, 1986). The structure of a closely related molecule has been reported by Muñoz et al. (2005).
The title compound was prepared in analogy to related compounds in the literature (King & Eisch, 1986). Single crystals were obtained by recrystallization from dichloromethane.
H atoms were geometrically positioned using fixed distances: C(sp2)-H = 0.95 Å, Csecondary—H = 0.99 Å and Uiso(H) = 1.2Ueq(C). The absolute configuration of the molecule was determined from the value of the Flack x parameter (Flack, 1983) using 2122 Friedel pairs. The maximum and minimum difference peaks are within 1Å from the Au atom.
The molecule has twofold symmetry and there is a crystallographic twofold axis passing through the midpoint of the C10—C10 bond. The naphthyl group is slightly bend: the angle between the planes of the two six-membered rings is 3.5 (5)°. Moreover atom C10 deviates 0.064 (5)Å from the plane through C1/C2/C3/C4/C9. The angle between the best planes of the two symmetry-related naphthyl groups is 84.4 (1)°. Both phenyl groups attached to P1 are essentially planar. The P—Au—Cl bond is almost linear with a bond angle of 175.5 (1)°. The dichloromethane solvate group also lies on a twofold axis. Its H atoms donate weak hydrogen bonds to Cl atoms of two symmetry-related Au—Cl groups (see Table). The crystal packing also shows a number of additional intermolecular C—H···Cl contacts with H···Cl distances between 3.00 and 3.15Å and a number of weak intermolecular C—H···π(benzene) interactions (Cg1, Cg2 and Cg3 are the centroids of the benzene rings labeled C1/C2/C3/C4/C9/C10, C4/C5/C6/C7/C8/C9 and C11/C12/C13/C14/C15/C16 respectively). The crystal structure of the corresponding bis(ditolylphosphino) compound has been reported by Muñoz et al. (2005). The conformation of that molecule, however, differs considerably from the conformation of the title compound.
Gold catalysis is becoming increasingly important (Hashmi & Hutchings, 2006) and the use of chiral gold complexes for enantioselective catalysis is one of the latest hot topics (Hashmi, 2005). In this context detailed structural information about these gold complexes is of high importance. Thus we conducted a crystal structure analysis of the title compound, which was prepared in analogy to related compounds (King & Eisch, 1986). The structure of a closely related molecule has been reported by Muñoz et al. (2005).
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1996); software used to prepare material for publication: SHELXL97.
[Au2Cl2(C44H32P2)]·CH2Cl2 | F(000) = 1120 |
Mr = 1172.40 | Dx = 1.933 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 124 reflections |
a = 19.480 (3) Å | θ = 3–23° |
b = 8.6889 (13) Å | µ = 7.65 mm−1 |
c = 14.085 (2) Å | T = 165 K |
β = 122.361 (15)° | Rod, colourless |
V = 2013.8 (6) Å3 | 0.55 × 0.08 × 0.06 mm |
Z = 2 |
Siemens SMART 1K CCD diffractometer | 4750 independent reflections |
Radiation source: normal-focus sealed tube | 3716 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
ω scans | θmax = 28.6°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | h = −26→25 |
Tmin = 0.459, Tmax = 0.632 | k = −11→11 |
15554 measured reflections | l = −18→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.077 | w = 1/[σ2(Fo2) + (0.03P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
4750 reflections | Δρmax = 1.40 e Å−3 |
240 parameters | Δρmin = −1.33 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: heavy-atom method | Absolute structure parameter: 0.003 (9) |
[Au2Cl2(C44H32P2)]·CH2Cl2 | V = 2013.8 (6) Å3 |
Mr = 1172.40 | Z = 2 |
Monoclinic, C2 | Mo Kα radiation |
a = 19.480 (3) Å | µ = 7.65 mm−1 |
b = 8.6889 (13) Å | T = 165 K |
c = 14.085 (2) Å | 0.55 × 0.08 × 0.06 mm |
β = 122.361 (15)° |
Siemens SMART 1K CCD diffractometer | 4750 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | 3716 reflections with I > 2σ(I) |
Tmin = 0.459, Tmax = 0.632 | Rint = 0.051 |
15554 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.077 | Δρmax = 1.40 e Å−3 |
S = 1.01 | Δρmin = −1.33 e Å−3 |
4750 reflections | Absolute structure: Flack (1983) |
240 parameters | Absolute structure parameter: 0.003 (9) |
1 restraint |
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 | ||
Au1 | 0.030660 (16) | 0.00085 (4) | 0.21397 (2) | 0.03045 (9) | |
Cl1 | −0.06153 (14) | −0.0668 (3) | 0.2601 (2) | 0.0431 (6) | |
Cl2 | −0.0766 (2) | 0.2910 (6) | 0.4864 (3) | 0.1173 (16) | |
P1 | 0.12613 (12) | 0.0508 (2) | 0.17702 (16) | 0.0231 (5) | |
C1 | 0.1051 (5) | 0.1638 (9) | 0.0544 (7) | 0.0165 (18) | |
C2 | 0.1626 (5) | 0.1598 (9) | 0.0248 (7) | 0.0254 (18) | |
H2A | 0.2095 | 0.0973 | 0.0670 | 0.030* | |
C3 | 0.1532 (5) | 0.2451 (9) | −0.0654 (7) | 0.030 (2) | |
H3A | 0.1933 | 0.2392 | −0.0841 | 0.036* | |
C4 | 0.0855 (5) | 0.3389 (8) | −0.1280 (6) | 0.0230 (17) | |
C5 | 0.0773 (6) | 0.4282 (9) | −0.2159 (7) | 0.034 (2) | |
H5A | 0.1161 | 0.4195 | −0.2369 | 0.041* | |
C6 | 0.0126 (6) | 0.5296 (11) | −0.2726 (7) | 0.038 (3) | |
H6A | 0.0080 | 0.5922 | −0.3310 | 0.046* | |
C7 | −0.0463 (5) | 0.5400 (8) | −0.2439 (7) | 0.034 (2) | |
H7A | −0.0908 | 0.6087 | −0.2838 | 0.041* | |
C8 | −0.0399 (5) | 0.4501 (8) | −0.1575 (6) | 0.0238 (18) | |
H8A | −0.0796 | 0.4586 | −0.1382 | 0.029* | |
C9 | 0.0256 (4) | 0.3467 (8) | −0.0985 (6) | 0.0205 (16) | |
C10 | 0.0334 (4) | 0.2521 (8) | −0.0094 (6) | 0.0188 (16) | |
C11 | 0.1655 (5) | −0.1328 (8) | 0.1610 (7) | 0.0244 (17) | |
C12 | 0.1319 (5) | −0.1978 (10) | 0.0548 (8) | 0.028 (2) | |
H12A | 0.0926 | −0.1418 | −0.0096 | 0.033* | |
C13 | 0.1546 (5) | −0.3407 (9) | 0.0421 (7) | 0.034 (2) | |
H13A | 0.1310 | −0.3831 | −0.0311 | 0.041* | |
C14 | 0.2102 (5) | −0.4225 (9) | 0.1318 (7) | 0.032 (2) | |
H14A | 0.2257 | −0.5219 | 0.1219 | 0.039* | |
C15 | 0.2445 (5) | −0.3616 (10) | 0.2380 (8) | 0.039 (2) | |
H15A | 0.2840 | −0.4186 | 0.3017 | 0.047* | |
C16 | 0.2207 (5) | −0.2143 (9) | 0.2517 (7) | 0.033 (2) | |
H16A | 0.2436 | −0.1724 | 0.3249 | 0.040* | |
C17 | 0.2116 (5) | 0.1490 (9) | 0.2941 (6) | 0.0265 (19) | |
C18 | 0.2862 (6) | 0.1502 (11) | 0.3116 (8) | 0.045 (2) | |
H18A | 0.2958 | 0.0933 | 0.2622 | 0.053* | |
C19 | 0.3532 (7) | 0.2352 (12) | 0.4034 (9) | 0.058 (3) | |
H19A | 0.4056 | 0.2341 | 0.4139 | 0.069* | |
C20 | 0.3388 (6) | 0.3176 (12) | 0.4750 (8) | 0.052 (3) | |
H20A | 0.3814 | 0.3743 | 0.5357 | 0.063* | |
C21 | 0.2618 (8) | 0.3168 (12) | 0.4574 (8) | 0.059 (3) | |
H21A | 0.2517 | 0.3740 | 0.5063 | 0.071* | |
C22 | 0.1985 (6) | 0.2331 (10) | 0.3689 (7) | 0.039 (2) | |
H22A | 0.1462 | 0.2328 | 0.3589 | 0.047* | |
C23 | 0.0000 | 0.178 (2) | 0.5000 | 0.073 (5) | |
H23A | −0.0212 | 0.1107 | 0.4330 | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Au1 | 0.03470 (15) | 0.02825 (14) | 0.03155 (14) | 0.0041 (2) | 0.01983 (12) | 0.0057 (3) |
Cl1 | 0.0461 (13) | 0.0405 (12) | 0.0593 (15) | 0.0033 (10) | 0.0393 (12) | 0.0099 (11) |
Cl2 | 0.061 (2) | 0.208 (5) | 0.073 (2) | 0.008 (3) | 0.029 (2) | −0.049 (3) |
P1 | 0.0270 (11) | 0.0210 (11) | 0.0246 (10) | 0.0053 (7) | 0.0160 (9) | 0.0023 (7) |
C1 | 0.025 (5) | 0.011 (4) | 0.019 (4) | −0.010 (3) | 0.016 (4) | −0.005 (3) |
C2 | 0.015 (4) | 0.027 (4) | 0.032 (5) | 0.004 (3) | 0.011 (4) | −0.006 (4) |
C3 | 0.035 (5) | 0.026 (4) | 0.050 (5) | −0.015 (4) | 0.037 (5) | −0.022 (4) |
C4 | 0.031 (5) | 0.013 (4) | 0.030 (4) | −0.008 (3) | 0.020 (4) | −0.006 (3) |
C5 | 0.055 (6) | 0.027 (4) | 0.039 (5) | −0.009 (4) | 0.038 (5) | −0.007 (4) |
C6 | 0.079 (6) | 0.021 (8) | 0.035 (4) | −0.007 (5) | 0.045 (5) | −0.001 (4) |
C7 | 0.049 (5) | 0.014 (6) | 0.035 (5) | 0.001 (3) | 0.020 (4) | 0.002 (3) |
C8 | 0.029 (4) | 0.021 (4) | 0.030 (4) | −0.003 (3) | 0.022 (4) | 0.000 (3) |
C9 | 0.024 (4) | 0.017 (4) | 0.021 (4) | −0.013 (3) | 0.013 (3) | −0.008 (3) |
C10 | 0.024 (4) | 0.018 (4) | 0.014 (4) | −0.003 (3) | 0.010 (3) | −0.002 (3) |
C11 | 0.023 (4) | 0.018 (4) | 0.037 (5) | 0.001 (3) | 0.019 (4) | −0.004 (3) |
C12 | 0.029 (6) | 0.016 (5) | 0.037 (5) | −0.001 (4) | 0.017 (5) | −0.005 (4) |
C13 | 0.036 (5) | 0.023 (4) | 0.043 (5) | −0.010 (4) | 0.020 (5) | −0.007 (4) |
C14 | 0.032 (5) | 0.019 (4) | 0.053 (6) | −0.007 (4) | 0.028 (5) | −0.004 (4) |
C15 | 0.042 (5) | 0.034 (5) | 0.048 (6) | 0.009 (4) | 0.029 (5) | 0.020 (4) |
C16 | 0.046 (6) | 0.024 (5) | 0.038 (5) | 0.009 (4) | 0.028 (5) | 0.007 (4) |
C17 | 0.034 (5) | 0.021 (4) | 0.021 (4) | 0.003 (3) | 0.013 (4) | 0.003 (3) |
C18 | 0.042 (6) | 0.047 (6) | 0.041 (6) | −0.004 (5) | 0.020 (5) | −0.020 (4) |
C19 | 0.052 (7) | 0.058 (7) | 0.048 (7) | 0.001 (5) | 0.017 (6) | 0.010 (5) |
C20 | 0.053 (7) | 0.064 (7) | 0.028 (5) | −0.023 (5) | 0.014 (5) | −0.003 (5) |
C21 | 0.099 (9) | 0.051 (7) | 0.033 (6) | −0.010 (6) | 0.039 (6) | −0.005 (5) |
C22 | 0.039 (5) | 0.056 (6) | 0.026 (5) | 0.000 (4) | 0.021 (4) | 0.006 (4) |
C23 | 0.072 (12) | 0.076 (11) | 0.102 (14) | 0.000 | 0.067 (11) | 0.000 |
Au1—P1 | 2.226 (2) | C11—C12 | 1.392 (12) |
Au1—Cl1 | 2.290 (2) | C12—C13 | 1.362 (11) |
Cl2—C23 | 1.712 (10) | C12—H12A | 0.9500 |
P1—C17 | 1.811 (8) | C13—C14 | 1.345 (11) |
P1—C1 | 1.833 (8) | C13—H13A | 0.9500 |
P1—C11 | 1.835 (7) | C14—C15 | 1.376 (12) |
C1—C2 | 1.388 (11) | C14—H14A | 0.9500 |
C1—C10 | 1.416 (11) | C15—C16 | 1.409 (11) |
C2—C3 | 1.395 (12) | C15—H15A | 0.9500 |
C2—H2A | 0.9500 | C16—H16A | 0.9500 |
C3—C4 | 1.393 (11) | C17—C18 | 1.338 (12) |
C3—H3A | 0.9500 | C17—C22 | 1.413 (11) |
C4—C5 | 1.396 (11) | C18—C19 | 1.454 (13) |
C4—C9 | 1.434 (10) | C18—H18A | 0.9500 |
C5—C6 | 1.386 (12) | C19—C20 | 1.383 (14) |
C5—H5A | 0.9500 | C19—H19A | 0.9500 |
C6—C7 | 1.409 (12) | C20—C21 | 1.384 (14) |
C6—H6A | 0.9500 | C20—H20A | 0.9500 |
C7—C8 | 1.394 (10) | C21—C22 | 1.400 (13) |
C7—H7A | 0.9500 | C21—H21A | 0.9500 |
C8—C9 | 1.410 (10) | C22—H22A | 0.9500 |
C8—H8A | 0.9500 | C23—Cl2ii | 1.712 (10) |
C9—C10 | 1.439 (10) | C23—H23A | 0.9900 |
C10—C10i | 1.459 (14) | C23—H23Aii | 0.9900 |
C11—C16 | 1.349 (11) | ||
P1—Au1—Cl1 | 175.47 (8) | C13—C12—C11 | 120.8 (8) |
C17—P1—C1 | 103.8 (4) | C13—C12—H12A | 119.6 |
C17—P1—C11 | 106.3 (4) | C11—C12—H12A | 119.6 |
C1—P1—C11 | 104.3 (4) | C14—C13—C12 | 120.9 (8) |
C17—P1—Au1 | 110.8 (3) | C14—C13—H13A | 119.6 |
C1—P1—Au1 | 122.1 (3) | C12—C13—H13A | 119.6 |
C11—P1—Au1 | 108.4 (2) | C13—C14—C15 | 119.8 (8) |
C2—C1—C10 | 120.3 (7) | C13—C14—H14A | 120.1 |
C2—C1—P1 | 117.4 (6) | C15—C14—H14A | 120.1 |
C10—C1—P1 | 122.3 (6) | C14—C15—C16 | 119.6 (8) |
C1—C2—C3 | 121.8 (7) | C14—C15—H15A | 120.2 |
C1—C2—H2A | 119.1 | C16—C15—H15A | 120.2 |
C3—C2—H2A | 119.1 | C11—C16—C15 | 120.1 (8) |
C4—C3—C2 | 120.3 (7) | C11—C16—H16A | 119.9 |
C4—C3—H3A | 119.8 | C15—C16—H16A | 119.9 |
C2—C3—H3A | 119.8 | C18—C17—C22 | 118.1 (8) |
C3—C4—C5 | 120.4 (8) | C18—C17—P1 | 123.3 (7) |
C3—C4—C9 | 119.1 (7) | C22—C17—P1 | 118.5 (7) |
C5—C4—C9 | 120.4 (7) | C17—C18—C19 | 122.5 (9) |
C6—C5—C4 | 120.1 (8) | C17—C18—H18A | 118.8 |
C6—C5—H5A | 120.0 | C19—C18—H18A | 118.8 |
C4—C5—H5A | 120.0 | C20—C19—C18 | 118.5 (10) |
C5—C6—C7 | 120.2 (8) | C20—C19—H19A | 120.8 |
C5—C6—H6A | 119.9 | C18—C19—H19A | 120.8 |
C7—C6—H6A | 119.9 | C19—C20—C21 | 119.4 (10) |
C8—C7—C6 | 120.6 (8) | C19—C20—H20A | 120.3 |
C8—C7—H7A | 119.7 | C21—C20—H20A | 120.3 |
C6—C7—H7A | 119.7 | C20—C21—C22 | 121.0 (10) |
C7—C8—C9 | 120.1 (7) | C20—C21—H21A | 119.5 |
C7—C8—H8A | 120.0 | C22—C21—H21A | 119.5 |
C9—C8—H8A | 120.0 | C21—C22—C17 | 120.6 (9) |
C8—C9—C4 | 118.6 (7) | C21—C22—H22A | 119.7 |
C8—C9—C10 | 121.2 (7) | C17—C22—H22A | 119.7 |
C4—C9—C10 | 120.2 (7) | Cl2—C23—Cl2ii | 109.7 (10) |
C1—C10—C9 | 118.1 (7) | Cl2—C23—H23A | 109.7 |
C1—C10—C10i | 123.9 (7) | Cl2ii—C23—H23A | 109.7 |
C9—C10—C10i | 118.0 (7) | Cl2—C23—H23Aii | 109.7 |
C16—C11—C12 | 118.9 (7) | Cl2ii—C23—H23Aii | 109.7 |
C16—C11—P1 | 120.9 (6) | H23A—C23—H23Aii | 108.2 |
C12—C11—P1 | 119.8 (6) | ||
C17—P1—C1—C2 | 68.2 (6) | C4—C9—C10—C10i | −173.6 (6) |
C11—P1—C1—C2 | −43.0 (6) | C17—P1—C11—C16 | 39.3 (8) |
Au1—P1—C1—C2 | −166.0 (5) | C1—P1—C11—C16 | 148.6 (7) |
C17—P1—C1—C10 | −112.1 (6) | Au1—P1—C11—C16 | −79.9 (7) |
C11—P1—C1—C10 | 136.7 (6) | C17—P1—C11—C12 | −147.8 (7) |
Au1—P1—C1—C10 | 13.7 (7) | C1—P1—C11—C12 | −38.5 (7) |
C10—C1—C2—C3 | 2.1 (11) | Au1—P1—C11—C12 | 93.1 (7) |
P1—C1—C2—C3 | −178.3 (6) | C16—C11—C12—C13 | −0.6 (13) |
C1—C2—C3—C4 | 0.6 (11) | P1—C11—C12—C13 | −173.6 (7) |
C2—C3—C4—C5 | 177.9 (7) | C11—C12—C13—C14 | 0.0 (14) |
C2—C3—C4—C9 | 0.1 (10) | C12—C13—C14—C15 | 0.1 (13) |
C3—C4—C5—C6 | −175.4 (7) | C13—C14—C15—C16 | 0.4 (12) |
C9—C4—C5—C6 | 2.4 (11) | C12—C11—C16—C15 | 1.1 (12) |
C4—C5—C6—C7 | −1.7 (12) | P1—C11—C16—C15 | 174.1 (6) |
C5—C6—C7—C8 | 0.8 (12) | C14—C15—C16—C11 | −1.0 (13) |
C6—C7—C8—C9 | −0.6 (11) | C1—P1—C17—C18 | −69.1 (8) |
C7—C8—C9—C4 | 1.3 (10) | C11—P1—C17—C18 | 40.6 (9) |
C7—C8—C9—C10 | −179.6 (6) | Au1—P1—C17—C18 | 158.1 (7) |
C3—C4—C9—C8 | 175.6 (6) | C1—P1—C17—C22 | 108.7 (7) |
C5—C4—C9—C8 | −2.2 (10) | C11—P1—C17—C22 | −141.6 (6) |
C3—C4—C9—C10 | −3.5 (10) | Au1—P1—C17—C22 | −24.0 (7) |
C5—C4—C9—C10 | 178.7 (7) | C22—C17—C18—C19 | −0.5 (14) |
C2—C1—C10—C9 | −5.3 (10) | P1—C17—C18—C19 | 177.3 (7) |
P1—C1—C10—C9 | 175.0 (5) | C17—C18—C19—C20 | 0.0 (15) |
C2—C1—C10—C10i | 174.3 (6) | C18—C19—C20—C21 | 0.0 (15) |
P1—C1—C10—C10i | −5.4 (9) | C19—C20—C21—C22 | 0.4 (15) |
C8—C9—C10—C1 | −173.0 (6) | C20—C21—C22—C17 | −0.9 (14) |
C4—C9—C10—C1 | 6.0 (10) | C18—C17—C22—C21 | 1.0 (13) |
C8—C9—C10—C10i | 7.4 (9) | P1—C17—C22—C21 | −177.0 (7) |
Symmetry codes: (i) −x, y, −z; (ii) −x, y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6A···Cl1iii | 0.95 | 3.12 | 3.614 (10) | 114 |
C15—H15A···Cl2iv | 0.95 | 3.15 | 3.618 (11) | 113 |
C16—H16A···Cl2iv | 0.95 | 3.00 | 3.542 (10) | 118 |
C19—H19A···Cl1v | 0.95 | 3.10 | 3.658 (14) | 120 |
C23—H23A···Cl1 | 0.99 | 2.62 | 3.611 (11) | 174 |
C3—H3A···Cg3vi | 0.95 | 2.89 | 3.837 | 179 |
C8—H8A···Cg3iii | 0.95 | 3.07 | 3.792 | 134 |
C13—H13A···Cg2vii | 0.95 | 2.61 | 3.447 | 147 |
C14—H14A···Cg1vii | 0.95 | 3.05 | 3.612 | 119 |
Symmetry codes: (iii) −x, y+1, −z; (iv) x+1/2, y−1/2, z; (v) x+1/2, y+1/2, z; (vi) −x+1/2, y+1/2, −z; (vii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [Au2Cl2(C44H32P2)]·CH2Cl2 |
Mr | 1172.40 |
Crystal system, space group | Monoclinic, C2 |
Temperature (K) | 165 |
a, b, c (Å) | 19.480 (3), 8.6889 (13), 14.085 (2) |
β (°) | 122.361 (15) |
V (Å3) | 2013.8 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 7.65 |
Crystal size (mm) | 0.55 × 0.08 × 0.06 |
Data collection | |
Diffractometer | Siemens SMART 1K CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2000) |
Tmin, Tmax | 0.459, 0.632 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15554, 4750, 3716 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.673 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.077, 1.01 |
No. of reflections | 4750 |
No. of parameters | 240 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.40, −1.33 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.003 (9) |
Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1996), SHELXL97.
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The molecule has twofold symmetry and there is a crystallographic twofold axis passing through the midpoint of the C10—C10 bond. The naphthyl group is slightly bend: the angle between the planes of the two six-membered rings is 3.5 (5)°. Moreover atom C10 deviates 0.064 (5)Å from the plane through C1/C2/C3/C4/C9. The angle between the best planes of the two symmetry-related naphthyl groups is 84.4 (1)°. Both phenyl groups attached to P1 are essentially planar. The P—Au—Cl bond is almost linear with a bond angle of 175.5 (1)°. The dichloromethane solvate group also lies on a twofold axis. Its H atoms donate weak hydrogen bonds to Cl atoms of two symmetry-related Au—Cl groups (see Table). The crystal packing also shows a number of additional intermolecular C—H···Cl contacts with H···Cl distances between 3.00 and 3.15Å and a number of weak intermolecular C—H···π(benzene) interactions (Cg1, Cg2 and Cg3 are the centroids of the benzene rings labeled C1/C2/C3/C4/C9/C10, C4/C5/C6/C7/C8/C9 and C11/C12/C13/C14/C15/C16 respectively). The crystal structure of the corresponding bis(ditolylphosphino) compound has been reported by Muñoz et al. (2005). The conformation of that molecule, however, differs considerably from the conformation of the title compound.