Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801010959/cv6037sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801010959/cv6037Isup2.hkl |
CCDC reference: 170895
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.004 Å
- R factor = 0.024
- wR factor = 0.067
- Data-to-parameter ratio = 15.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The title compound was prepared according to the literature method of Tzschach & Lange (1962). Crystals of suitable quality for single-crystal X-ray diffraction studies were obtained by evaporation of a 1:1 v/v dichloromethane/acetonitrile solution of dpae and SbCl3 during the attempted preparation of a complex.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-1999); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976).
Fig. 1. The molecular structure of (I) showing the atom-labelling scheme. Ellipsoids are drawn at the 40% probability level and H atoms have been omitted for clarity. |
C26H24As2 | F(000) = 492 |
Mr = 486.29 | Dx = 1.469 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.078 (1) Å | Cell parameters from 25 reflections |
b = 5.761 (2) Å | θ = 19.2–23.8° |
c = 21.372 (2) Å | µ = 3.05 mm−1 |
β = 100.341 (8)° | T = 150 K |
V = 1099.6 (4) Å3 | Needle, colourless |
Z = 2 | 0.60 × 0.45 × 0.38 mm |
Rigaku AFC-7S diffractometer | 1700 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.016 |
Graphite monochromator | θmax = 25.0°, θmin = 2.3° |
ω–2θ scans | h = 0→10 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→6 |
Tmin = 0.224, Tmax = 0.314 | l = −25→24 |
2061 measured reflections | 3 standard reflections every 150 reflections |
1932 independent reflections | intensity decay: none |
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)] = 0.024 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.067 | Only H-atom displacement parameters refined |
S = 1.10 | w = 1/[σ2(Fo2) + (0.032P)2 + 0.5P] where P = (Fo2 + 2Fc2)/3 |
1932 reflections | (Δ/σ)max = 0.007 |
128 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
C26H24As2 | V = 1099.6 (4) Å3 |
Mr = 486.29 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.078 (1) Å | µ = 3.05 mm−1 |
b = 5.761 (2) Å | T = 150 K |
c = 21.372 (2) Å | 0.60 × 0.45 × 0.38 mm |
β = 100.341 (8)° |
Rigaku AFC-7S diffractometer | 1700 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.016 |
Tmin = 0.224, Tmax = 0.314 | 3 standard reflections every 150 reflections |
2061 measured reflections | intensity decay: none |
1932 independent reflections |
R[F2 > 2σ(F2)] = 0.024 | 0 restraints |
wR(F2) = 0.067 | Only H-atom displacement parameters refined |
S = 1.10 | Δρmax = 0.23 e Å−3 |
1932 reflections | Δρmin = −0.44 e Å−3 |
128 parameters |
Experimental. The large collimator (1.0 mm dia) was used because of the large crystal size. |
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. H atoms although observed in later electron density maps were placed in calculated positions and given a common refined adp. |
x | y | z | Uiso*/Ueq | ||
As1 | 0.70352 (3) | 0.21943 (4) | 0.051511 (11) | 0.02686 (11) | |
C1 | 0.5816 (3) | −0.0362 (4) | 0.00791 (11) | 0.0283 (5) | |
H1A | 0.6179 | −0.0770 | −0.0317 | 0.045 (2)* | |
H1B | 0.5917 | −0.1750 | 0.0357 | 0.045 (2)* | |
C2 | 0.8936 (3) | 0.0559 (5) | 0.07924 (11) | 0.0298 (6) | |
C3 | 0.9284 (3) | −0.1583 (5) | 0.05606 (13) | 0.0376 (6) | |
H3 | 0.8545 | −0.2411 | 0.0275 | 0.045 (2)* | |
C4 | 1.0703 (4) | −0.2526 (6) | 0.07429 (17) | 0.0515 (9) | |
H4 | 1.0928 | −0.3989 | 0.0578 | 0.045 (2)* | |
C5 | 1.1782 (3) | −0.1375 (7) | 0.11570 (17) | 0.0589 (10) | |
H5 | 1.2751 | −0.2031 | 0.1279 | 0.045 (2)* | |
C6 | 1.1447 (3) | 0.0753 (7) | 0.13961 (15) | 0.0556 (10) | |
H6 | 1.2192 | 0.1559 | 0.1684 | 0.045 (2)* | |
C7 | 1.0037 (3) | 0.1724 (6) | 0.12201 (13) | 0.0412 (7) | |
H7 | 0.9818 | 0.3182 | 0.1390 | 0.045 (2)* | |
C8 | 0.6284 (3) | 0.2035 (4) | 0.13179 (11) | 0.0258 (5) | |
C9 | 0.5453 (3) | 0.3902 (4) | 0.14893 (12) | 0.0318 (6) | |
H9 | 0.5250 | 0.5202 | 0.1214 | 0.045 (2)* | |
C10 | 0.4924 (3) | 0.3864 (5) | 0.20615 (12) | 0.0352 (6) | |
H10 | 0.4355 | 0.5132 | 0.2174 | 0.045 (2)* | |
C11 | 0.5224 (3) | 0.1988 (5) | 0.24640 (13) | 0.0353 (6) | |
H11 | 0.4868 | 0.1972 | 0.2856 | 0.045 (2)* | |
C12 | 0.6041 (3) | 0.0128 (5) | 0.23007 (12) | 0.0333 (6) | |
H12 | 0.6242 | −0.1164 | 0.2579 | 0.045 (2)* | |
C13 | 0.6566 (3) | 0.0151 (5) | 0.17289 (11) | 0.0297 (5) | |
H13 | 0.7123 | −0.1132 | 0.1618 | 0.045 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
As1 | 0.02922 (16) | 0.02813 (17) | 0.02292 (16) | −0.00342 (10) | 0.00383 (11) | 0.00190 (10) |
C1 | 0.0296 (13) | 0.0321 (13) | 0.0230 (12) | −0.0022 (11) | 0.0042 (10) | −0.0030 (10) |
C2 | 0.0257 (13) | 0.0398 (15) | 0.0246 (13) | −0.0041 (11) | 0.0065 (10) | 0.0058 (11) |
C3 | 0.0379 (15) | 0.0428 (16) | 0.0344 (15) | 0.0029 (13) | 0.0124 (12) | 0.0065 (13) |
C4 | 0.0519 (19) | 0.056 (2) | 0.054 (2) | 0.0174 (16) | 0.0288 (17) | 0.0229 (16) |
C5 | 0.0305 (16) | 0.091 (3) | 0.058 (2) | 0.0135 (18) | 0.0170 (15) | 0.040 (2) |
C6 | 0.0301 (15) | 0.089 (3) | 0.0447 (18) | −0.0183 (17) | −0.0018 (13) | 0.0208 (19) |
C7 | 0.0351 (14) | 0.0522 (18) | 0.0369 (15) | −0.0138 (14) | 0.0077 (12) | 0.0047 (14) |
C8 | 0.0248 (12) | 0.0300 (13) | 0.0212 (12) | −0.0046 (10) | 0.0004 (9) | −0.0028 (10) |
C9 | 0.0348 (14) | 0.0256 (13) | 0.0338 (14) | 0.0000 (11) | 0.0029 (11) | 0.0000 (11) |
C10 | 0.0346 (14) | 0.0375 (15) | 0.0335 (14) | 0.0038 (12) | 0.0062 (11) | −0.0077 (12) |
C11 | 0.0335 (14) | 0.0485 (17) | 0.0242 (13) | −0.0034 (12) | 0.0064 (11) | −0.0058 (12) |
C12 | 0.0353 (14) | 0.0392 (15) | 0.0248 (12) | −0.0006 (12) | 0.0042 (10) | 0.0030 (11) |
C13 | 0.0302 (13) | 0.0329 (13) | 0.0251 (12) | 0.0015 (11) | 0.0025 (10) | −0.0007 (11) |
As1—C8 | 1.959 (2) | C6—C7 | 1.385 (4) |
As1—C2 | 1.962 (3) | C6—H6 | 0.9500 |
As1—C1 | 1.973 (2) | C7—H7 | 0.9500 |
C1—C1i | 1.518 (5) | C8—C13 | 1.391 (3) |
C1—H1A | 0.9900 | C8—C9 | 1.400 (4) |
C1—H1B | 0.9900 | C9—C10 | 1.392 (4) |
C2—C3 | 1.387 (4) | C9—H9 | 0.9500 |
C2—C7 | 1.399 (4) | C10—C11 | 1.378 (4) |
C3—C4 | 1.388 (4) | C10—H10 | 0.9500 |
C3—H3 | 0.9500 | C11—C12 | 1.383 (4) |
C4—C5 | 1.368 (5) | C11—H11 | 0.9500 |
C4—H4 | 0.9500 | C12—C13 | 1.389 (3) |
C5—C6 | 1.383 (5) | C12—H12 | 0.9500 |
C5—H5 | 0.9500 | C13—H13 | 0.9500 |
C8—As1—C2 | 97.95 (10) | C7—C6—H6 | 119.6 |
C8—As1—C1 | 97.18 (10) | C6—C7—C2 | 120.0 (3) |
C2—As1—C1 | 99.93 (11) | C6—C7—H7 | 120.0 |
C1i—C1—As1 | 110.0 (2) | C2—C7—H7 | 120.0 |
C1i—C1—H1A | 109.7 | C13—C8—C9 | 118.8 (2) |
As1—C1—H1A | 109.7 | C13—C8—As1 | 122.43 (19) |
C1i—C1—H1B | 109.7 | C9—C8—As1 | 118.81 (19) |
As1—C1—H1B | 109.7 | C10—C9—C8 | 120.3 (2) |
H1A—C1—H1B | 108.2 | C10—C9—H9 | 119.8 |
C3—C2—C7 | 118.6 (3) | C8—C9—H9 | 119.8 |
C3—C2—As1 | 124.3 (2) | C11—C10—C9 | 120.0 (2) |
C7—C2—As1 | 117.0 (2) | C11—C10—H10 | 120.0 |
C2—C3—C4 | 120.5 (3) | C9—C10—H10 | 120.0 |
C2—C3—H3 | 119.8 | C10—C11—C12 | 120.3 (2) |
C4—C3—H3 | 119.8 | C10—C11—H11 | 119.8 |
C5—C4—C3 | 120.8 (3) | C12—C11—H11 | 119.8 |
C5—C4—H4 | 119.6 | C11—C12—C13 | 119.9 (3) |
C3—C4—H4 | 119.6 | C11—C12—H12 | 120.0 |
C4—C5—C6 | 119.3 (3) | C13—C12—H12 | 120.0 |
C4—C5—H5 | 120.3 | C12—C13—C8 | 120.7 (2) |
C6—C5—H5 | 120.3 | C12—C13—H13 | 119.7 |
C5—C6—C7 | 120.7 (3) | C8—C13—H13 | 119.7 |
C5—C6—H6 | 119.6 |
Symmetry code: (i) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C26H24As2 |
Mr | 486.29 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 150 |
a, b, c (Å) | 9.078 (1), 5.761 (2), 21.372 (2) |
β (°) | 100.341 (8) |
V (Å3) | 1099.6 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 3.05 |
Crystal size (mm) | 0.60 × 0.45 × 0.38 |
Data collection | |
Diffractometer | Rigaku AFC-7S diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.224, 0.314 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2061, 1932, 1700 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.067, 1.10 |
No. of reflections | 1932 |
No. of parameters | 128 |
H-atom treatment | Only H-atom displacement parameters refined |
Δρmax, Δρmin (e Å−3) | 0.23, −0.44 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988), MSC/AFC Diffractometer Control Software, TEXSAN for Windows (Molecular Structure Corporation, 1997-1999), SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976).
As1—C8 | 1.959 (2) | As1—C1 | 1.973 (2) |
As1—C2 | 1.962 (3) | C1—C1i | 1.518 (5) |
C8—As1—C2 | 97.95 (10) | C3—C2—As1 | 124.3 (2) |
C8—As1—C1 | 97.18 (10) | C7—C2—As1 | 117.0 (2) |
C2—As1—C1 | 99.93 (11) | C13—C8—C9 | 118.8 (2) |
C1i—C1—As1 | 110.0 (2) | C13—C8—As1 | 122.43 (19) |
C3—C2—C7 | 118.6 (3) | C9—C8—As1 | 118.81 (19) |
Symmetry code: (i) −x+1, −y, −z. |
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During the course of our work on antimony(III) and bismuth(III) complexes of multidentate tertiary phosphine and arsine ligands (Genge et al., 2001), 1,2-bis(diphenylarsino)ethane [(I), dpae] was isolated as colourless needles from an attempted preparation of the complex [SbCl3(dpae)]. This ligand is commercially available and has been widely used although the crystal structure has not been reported.
The literature contains a number of structural reports concerning transition metal complexes of this ligand: [Pd3(µ3-S)2(dpae)3][BPh4]2 (Matsumoto et al., 1999), [Ru(dpae)2I2][BF4] (Champness et al., 1996), [Os(N)Cl3(dpae)] (Lam et al., 1993), [ReN(dpae)2Cl][ClO4] (Yam et al., 1992), [ReH5(PPh3)2(dpae)] (Costello et al., 1991), [Re2Cl4(dpae)2] and [ReCl(dpae)2]2[Re2Cl8] (Ferry et al., 1989), and [Ag(NO3)2(dpae)] (Pelizzi et al., 1985).
The title structure contains discrete centrosymmetric molecules (Fig. 1 and Table 1) with typical values for the C—C and As—C bond lengths. It has been noted for Ph3M complexes (M = Sb or As) (Holmes et al., 1998) that the mean C—M—C angle increases upon coordination and the same trend is observed in the compound under study. Inspection of the Cambridge Structural Database (CSD; Allen & Kennard, 1993) gave the average C—As—C bond angle in the small sample (22 observations) of dpae complexes of 103.9° (maximum 106.9°, minimum 98.9°), compared with an angle of 98.4° in the free ligand.