Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029545/ob6589sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029545/ob6589Isup2.hkl |
CCDC reference: 287689
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.039
- wR factor = 0.096
- Data-to-parameter ratio = 18.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 2 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C1 - C2 ... 1.37 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C1 - C6 ... 1.39 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C7 - C8 ... 1.37 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C7 - C12 ... 1.39 Ang. PLAT711_ALERT_1_C BOND Unknown or Inconsistent Label .......... AS/P AS/P C13 PLAT711_ALERT_1_C BOND Unknown or Inconsistent Label .......... AS/P AS/P C1 PLAT711_ALERT_1_C BOND Unknown or Inconsistent Label .......... AS/P AS/P C7 PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... AS/P C13 AS/P C1 PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... AS/P C13 AS/P C7 PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... AS/P C1 AS/P C7 PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... AS/P C2 C1 AS/P PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... AS/P C6 C1 AS/P PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... AS/P C8 C7 AS/P PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... AS/P C12 C7 AS/P PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... AS/P C13 C13 AS/P
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 18 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 12 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
The compound was supplied by Strem Chemicals. Single crystals of (I) were obtained by slow evaporation of an ethanol solution.
The site-occupancy factors of the As and P atoms were fixed at 1/2, and the same positional and atomic displacement parameters were assumed. The methylene H atoms were located in difference density maps and their coordinates were refined [C—H = 0.93 (3)–0.95 (3) Å]. The phenyl H atoms were placed at calculated positions and refined using a riding model, with C—H = 0.93 Å. All H-atom Uiso parameters were fixed at 1.2Ueq(C).
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).
Fig. 1. The molecular structure of (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 25% probability level. |
C26H24AsP | F(000) = 456 |
Mr = 442.34 | Dx = 1.323 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 40 reflections |
a = 9.1011 (6) Å | θ = 9.9–24.3° |
b = 5.7856 (8) Å | µ = 1.61 mm−1 |
c = 21.4502 (10) Å | T = 293 K |
β = 100.557 (5)° | Prism, colorless |
V = 1110.35 (18) Å3 | 0.22 × 0.16 × 0.12 mm |
Z = 2 |
Siemens P4 diffractometer | Rint = 0.034 |
θ/2θ scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: ψ scan (Siemens, 1994) | h = −1→11 |
Tmin = 0.744, Tmax = 0.826 | k = −1→7 |
3557 measured reflections | l = −27→27 |
2520 independent reflections | 3 standard reflections every 60 min |
1579 reflections with I > 2σ(I) | intensity decay: 0.2% |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.041P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.096 | (Δ/σ)max < 0.001 |
S = 0.95 | Δρmax = 0.29 e Å−3 |
2520 reflections | Δρmin = −0.34 e Å−3 |
133 parameters |
C26H24AsP | V = 1110.35 (18) Å3 |
Mr = 442.34 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.1011 (6) Å | µ = 1.61 mm−1 |
b = 5.7856 (8) Å | T = 293 K |
c = 21.4502 (10) Å | 0.22 × 0.16 × 0.12 mm |
β = 100.557 (5)° |
Siemens P4 diffractometer | 1579 reflections with I > 2σ(I) |
Absorption correction: ψ scan (Siemens, 1994) | Rint = 0.034 |
Tmin = 0.744, Tmax = 0.826 | 3 standard reflections every 60 min |
3557 measured reflections | intensity decay: 0.2% |
2520 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.096 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | Δρmax = 0.29 e Å−3 |
2520 reflections | Δρmin = −0.34 e Å−3 |
133 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
As | 0.80176 (4) | 0.21063 (7) | 0.948461 (16) | 0.05341 (16) | 0.5 |
P | 0.80176 (4) | 0.21063 (7) | 0.948461 (16) | 0.05341 (16) | 0.5 |
C1 | 0.6154 (3) | 0.0560 (5) | 0.92113 (11) | 0.0539 (7) | |
C2 | 0.5766 (3) | −0.1532 (6) | 0.94320 (13) | 0.0701 (8) | |
H2 | 0.6474 | −0.2381 | 0.9707 | 0.084* | |
C3 | 0.4318 (4) | −0.2409 (7) | 0.92488 (19) | 0.0958 (13) | |
H3 | 0.4061 | −0.3824 | 0.9404 | 0.115* | |
C4 | 0.3272 (4) | −0.1156 (10) | 0.8835 (2) | 0.1104 (16) | |
H4 | 0.2309 | −0.1727 | 0.8709 | 0.132* | |
C5 | 0.3659 (4) | 0.0912 (9) | 0.86138 (18) | 0.1017 (14) | |
H5 | 0.2954 | 0.1745 | 0.8333 | 0.122* | |
C6 | 0.5079 (3) | 0.1799 (7) | 0.87987 (14) | 0.0784 (10) | |
H6 | 0.5319 | 0.323 | 0.8647 | 0.094* | |
C7 | 0.8735 (3) | 0.1948 (5) | 0.87003 (11) | 0.0486 (6) | |
C8 | 0.8461 (3) | 0.0133 (5) | 0.82838 (11) | 0.0549 (7) | |
H8 | 0.7907 | −0.112 | 0.8383 | 0.066* | |
C9 | 0.8992 (3) | 0.0128 (6) | 0.77185 (11) | 0.0643 (8) | |
H9 | 0.8802 | −0.1121 | 0.7443 | 0.077* | |
C10 | 0.9800 (3) | 0.1984 (6) | 0.75691 (13) | 0.0680 (8) | |
H10 | 1.0152 | 0.1994 | 0.7189 | 0.082* | |
C11 | 1.0091 (3) | 0.3810 (6) | 0.79726 (14) | 0.0700 (8) | |
H11 | 1.064 | 0.5061 | 0.7868 | 0.084* | |
C12 | 0.9564 (3) | 0.3799 (5) | 0.85405 (12) | 0.0617 (7) | |
H12 | 0.9769 | 0.5045 | 0.8817 | 0.074* | |
C13 | 0.9184 (3) | −0.0356 (6) | 0.99143 (12) | 0.0542 (7) | |
H13A | 0.877 (3) | −0.069 (5) | 1.0281 (11) | 0.065* | |
H13B | 0.909 (3) | −0.172 (5) | 0.9676 (13) | 0.065* |
U11 | U22 | U33 | U12 | U13 | U23 | |
As | 0.0504 (2) | 0.0638 (3) | 0.0447 (2) | 0.0085 (2) | 0.00517 (15) | −0.00239 (19) |
P | 0.0504 (2) | 0.0638 (3) | 0.0447 (2) | 0.0085 (2) | 0.00517 (15) | −0.00239 (19) |
C1 | 0.0430 (14) | 0.073 (2) | 0.0454 (13) | 0.0087 (14) | 0.0074 (11) | −0.0079 (13) |
C2 | 0.0617 (18) | 0.084 (2) | 0.0659 (17) | −0.0023 (17) | 0.0163 (14) | −0.0133 (17) |
C3 | 0.084 (2) | 0.115 (3) | 0.099 (3) | −0.031 (2) | 0.046 (2) | −0.041 (2) |
C4 | 0.050 (2) | 0.180 (5) | 0.105 (3) | −0.019 (3) | 0.023 (2) | −0.072 (3) |
C5 | 0.048 (2) | 0.162 (4) | 0.090 (2) | 0.028 (3) | −0.0022 (18) | −0.029 (3) |
C6 | 0.0561 (17) | 0.111 (3) | 0.0670 (17) | 0.0219 (19) | 0.0075 (14) | −0.0008 (18) |
C7 | 0.0432 (13) | 0.0579 (16) | 0.0422 (11) | 0.0057 (13) | 0.0011 (10) | 0.0045 (12) |
C8 | 0.0529 (16) | 0.0631 (18) | 0.0475 (12) | −0.0044 (14) | 0.0060 (12) | 0.0005 (13) |
C9 | 0.0596 (17) | 0.087 (2) | 0.0459 (13) | −0.0036 (17) | 0.0085 (13) | −0.0055 (14) |
C10 | 0.0562 (16) | 0.101 (2) | 0.0476 (13) | 0.0117 (19) | 0.0119 (12) | 0.0140 (17) |
C11 | 0.0628 (18) | 0.080 (2) | 0.0685 (18) | −0.0052 (17) | 0.0164 (15) | 0.0160 (17) |
C12 | 0.0614 (17) | 0.0577 (17) | 0.0626 (16) | 0.0011 (16) | 0.0026 (14) | −0.0024 (14) |
C13 | 0.0486 (15) | 0.073 (2) | 0.0402 (13) | 0.0033 (15) | 0.0061 (12) | 0.0011 (13) |
As/P—C13 | 1.910 (3) | C7—C8 | 1.371 (4) |
As/P—C1 | 1.912 (3) | C7—C12 | 1.389 (4) |
As/P—C7 | 1.915 (2) | C8—C9 | 1.385 (3) |
C1—C2 | 1.369 (4) | C8—H8 | 0.93 |
C1—C6 | 1.392 (4) | C9—C10 | 1.372 (4) |
C2—C3 | 1.400 (4) | C9—H9 | 0.93 |
C2—H2 | 0.93 | C10—C11 | 1.361 (4) |
C3—C4 | 1.382 (6) | C10—H10 | 0.93 |
C3—H3 | 0.93 | C11—C12 | 1.388 (4) |
C4—C5 | 1.357 (6) | C11—H11 | 0.93 |
C4—H4 | 0.93 | C12—H12 | 0.93 |
C5—C6 | 1.380 (5) | C13—C13i | 1.520 (5) |
C5—H5 | 0.93 | C13—H13A | 0.95 (3) |
C6—H6 | 0.93 | C13—H13B | 0.93 (3) |
C13—As/P—C1 | 100.51 (13) | C12—C7—As/P | 117.9 (2) |
C13—As/P—C7 | 98.01 (11) | C7—C8—C9 | 121.4 (3) |
C1—As/P—C7 | 97.72 (10) | C7—C8—H8 | 119.3 |
C2—C1—C6 | 118.7 (3) | C9—C8—H8 | 119.3 |
C2—C1—As/P | 125.3 (2) | C10—C9—C8 | 119.4 (3) |
C6—C1—As/P | 115.8 (2) | C10—C9—H9 | 120.3 |
C1—C2—C3 | 120.8 (3) | C8—C9—H9 | 120.3 |
C1—C2—H2 | 119.6 | C11—C10—C9 | 120.6 (3) |
C3—C2—H2 | 119.6 | C11—C10—H10 | 119.7 |
C4—C3—C2 | 119.5 (4) | C9—C10—H10 | 119.7 |
C4—C3—H3 | 120.3 | C10—C11—C12 | 119.7 (3) |
C2—C3—H3 | 120.3 | C10—C11—H11 | 120.1 |
C5—C4—C3 | 119.7 (4) | C12—C11—H11 | 120.1 |
C5—C4—H4 | 120.2 | C11—C12—C7 | 120.7 (3) |
C3—C4—H4 | 120.2 | C11—C12—H12 | 119.7 |
C4—C5—C6 | 121.1 (4) | C7—C12—H12 | 119.7 |
C4—C5—H5 | 119.4 | C13i—C13—As/P | 110.3 (3) |
C6—C5—H5 | 119.4 | C13i—C13—H13A | 111.8 (15) |
C5—C6—C1 | 120.2 (4) | As—C13—H13A | 106.3 (16) |
C5—C6—H6 | 119.9 | C13i—C13—H13B | 110.6 (18) |
C1—C6—H6 | 119.9 | As—C13—H13B | 112.0 (17) |
C8—C7—C12 | 118.2 (2) | H13A—C13—H13B | 106 (2) |
C8—C7—As/P | 123.9 (2) | ||
C13—As—C1—C2 | 14.8 (3) | C1—As—C7—C8 | −34.4 (2) |
C7—As—C1—C2 | 114.4 (2) | C13—As—C7—C12 | −113.6 (2) |
C13—As—C1—C6 | −171.4 (2) | C1—As—C7—C12 | 144.6 (2) |
C7—As—C1—C6 | −71.8 (2) | C12—C7—C8—C9 | 0.0 (4) |
C6—C1—C2—C3 | −0.2 (4) | As—C7—C8—C9 | 179.1 (2) |
As—C1—C2—C3 | 173.4 (2) | C7—C8—C9—C10 | −0.5 (4) |
C1—C2—C3—C4 | 0.7 (5) | C8—C9—C10—C11 | 0.5 (4) |
C2—C3—C4—C5 | −0.3 (5) | C9—C10—C11—C12 | −0.1 (4) |
C3—C4—C5—C6 | −0.5 (6) | C10—C11—C12—C7 | −0.4 (4) |
C4—C5—C6—C1 | 1.0 (5) | C8—C7—C12—C11 | 0.4 (4) |
C2—C1—C6—C5 | −0.6 (4) | As—C7—C12—C11 | −178.7 (2) |
As—C1—C6—C5 | −174.8 (2) | C1—As—C13—C13i | 170.7 (2) |
C13—As—C7—C8 | 67.4 (2) | C7—As—C13—C13i | 71.3 (3) |
Symmetry code: (i) −x+2, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C26H24AsP |
Mr | 442.34 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 9.1011 (6), 5.7856 (8), 21.4502 (10) |
β (°) | 100.557 (5) |
V (Å3) | 1110.35 (18) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.61 |
Crystal size (mm) | 0.22 × 0.16 × 0.12 |
Data collection | |
Diffractometer | Siemens P4 diffractometer |
Absorption correction | ψ scan (Siemens, 1994) |
Tmin, Tmax | 0.744, 0.826 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3557, 2520, 1579 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.096, 0.95 |
No. of reflections | 2520 |
No. of parameters | 133 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.29, −0.34 |
Computer programs: XSCANS (Siemens, 1994), XSCANS, SHELXS86 (Sheldrick, 1985), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX publication routines (Farrugia, 1999).
As/P—C13 | 1.910 (3) | As/P—C7 | 1.915 (2) |
As/P—C1 | 1.912 (3) | C13—C13i | 1.520 (5) |
C13—As/P—C1 | 100.51 (13) | C6—C1—As/P | 115.8 (2) |
C13—As/P—C7 | 98.01 (11) | C8—C7—C12 | 118.2 (2) |
C1—As/P—C7 | 97.72 (10) | C8—C7—As/P | 123.9 (2) |
C2—C1—C6 | 118.7 (3) | C12—C7—As/P | 117.9 (2) |
C2—C1—As/P | 125.3 (2) | C13i—C13—As/P | 110.3 (3) |
Symmetry code: (i) −x+2, −y, −z+2. |
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There have been numerous X-ray structural determinations of tertiary phosphines and also tertiary arsines which are widely used as ligands in organo-transition metal chemistry. However, X-ray structure determinations of ligands containing both P and As atoms are rare. As part of our study on the substitution of transition metal–carbonyl clusters with mixed ligand complexes, we have published several structures of triruthenium–carbonyl clusters containing mixed P/As (Shawkataly et al., 1998) or P/Sb ligands (Shawkataly et al., 2004). A search of the November 2004 release of Cambridge Structural Database (Allen, 2002) revealed only 20 structures of complexes containing the above ligands. The title compound, (I), is commercially available and has been widely used, though the crystal structure has not been reported.
The crystal structure of (I) is isomorphous with those of Ph2P(CH2)2PPh2 (Pelizzi & Pelizzi, 1979) and Ph2As(CH2)2AsPh2 (Hill et al., 2001); all these compounds have a crystallographic inversion centerat the middle of the Csp3—Csp3 bond. However, in (I), this means a positional disorder of the As and P atoms (Fig. 1). The positional disorder between the As/P atoms was also observed in Ru3(CO)8(Ph2AsCH2AsPh2)(Ph2PCH2PPh2) (Shawkataly et al., 1998).