Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030553/lh2435sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030553/lh2435Isup2.hkl |
CCDC reference: 655054
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.063
- wR factor = 0.197
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.20 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.24 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C11 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT320_ALERT_2_C Check Hybridisation of C1 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT367_ALERT_2_C Long? C(sp?)-C(sp?) Bond C1 - C1_a ... 1.69 Ang. PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.13 Ratio
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For synthesis see: Alexander & Schroeder (1963) and for related structures see: Zhang et al. (2006); Kivekäs et al. (1995).
The title compound was synthesizd according to the literature method (Alexander & Schroeder, 1963). But in our synthesis diphenylchorophosphine was substituted with dicyclohexylchorophosphine. A white solid was dissolved in dichloromethane, and crystals suitable for X-ray diffraction were obtained after partial evaporation (65.2%, m.p. 528–529 K). FTIR (KBr) v (cm-l): 2928,2850 (C–H); 2643,2622,2599,2555 (B–H).
All H atoms were placed geometrically and treated as riding on their parent atoms, with B—H 1.10, C—H 0.97 (methylene) C—H 0.98 Å (hypomethyl), with Uiso(H) = 1.2Ueq(B,C).
The structure of 1,2-(PPh2)-1,2-C2B10H10 (Zhang et al., 2006) has recently been reported and was synthesized by the method of Alexander & Schroeder (1963). In addition, 1,2-(PiPr2)2-1,2-C2B10H10 was synthesized and characterized by Kivekäs et al. (1995). Since then, many complexes containing the above two lignads have been reported. We are interested in phosphine derivatives of 1,2-dicarba-closo-dodecaborane. In this paper, we report the structure of 1,2-bis(dicyclohexylphosphino)-1,2-dicarba-closo-dodecaborane.
As shown in Fig. 1, the molecular structure of the title compound has crystallographic twofold rotation symmetry. The P atom of dicyclohexylphosphine group is bonded to C1. The P—C1 distance is 1.894 (3) Å, which is agreement well with the corresponding distance 1.894 (3) Å in 1,2-(PiPr2)2-1,2-C2B10H10 and 1.885 Å in 1,2-(PPh2)-1,2-C2B10H10. The P—C1—C1i angle [symmetry code (i): 1 - x, y, 1/2 - z] in 1,2-(PCycl2)-1,2-C2B10H10 is 113.48 (5)°. The corresponding angles in 1,2-(PPh2)-1,2-C2B10H10 (Zhang et al., 2006) and 1,2-(PiPr2)2-1,2-C2B10H10 (Kivekäs et al., 1995) are 116.6 (2),111.07 (19)° and 112.9 (2),112.3 (1)° respectively. The two phosphorus and two cage C atoms are almost coplanar with the torsion angle 10.9 (4)°, which is samller than that of 12.1 (2)° for 1,2-(PiPr2)2-1,2-C2B10H10 (Kivekäs et al., 1995), and almost equal to that of 10.6 (3)° for 1,2-(PPh2)-1,2-C2B10H10 (Zhang et al., 2006).
For synthesis see: Alexander & Schroeder (1963) and for related structures see: Zhang et al. (2006); Kivekäs et al. (1995).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure with atom labels and 40% probability displacement ellipsoids for non-H atoms. |
C26H54B10P2 | F(000) = 1160 |
Mr = 536.73 | Dx = 1.109 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1912 reflections |
a = 21.507 (2) Å | θ = 2.3–26.8° |
b = 10.0350 (14) Å | µ = 0.15 mm−1 |
c = 15.2976 (18) Å | T = 298 K |
β = 103.196 (2)° | Block, colorless |
V = 3214.4 (7) Å3 | 0.58 × 0.57 × 0.46 mm |
Z = 4 |
Bruker SMART CCD diffractometer | 2743 independent reflections |
Radiation source: fine-focus sealed tube | 1814 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
φ and ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −25→19 |
Tmin = 0.917, Tmax = 0.934 | k = −11→10 |
6226 measured reflections | l = −17→18 |
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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.197 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.095P)2 + 4.2002P] where P = (Fo2 + 2Fc2)/3 |
2743 reflections | (Δ/σ)max < 0.001 |
172 parameters | Δρmax = 0.84 e Å−3 |
1 restraint | Δρmin = −0.26 e Å−3 |
C26H54B10P2 | V = 3214.4 (7) Å3 |
Mr = 536.73 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 21.507 (2) Å | µ = 0.15 mm−1 |
b = 10.0350 (14) Å | T = 298 K |
c = 15.2976 (18) Å | 0.58 × 0.57 × 0.46 mm |
β = 103.196 (2)° |
Bruker SMART CCD diffractometer | 2743 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1814 reflections with I > 2σ(I) |
Tmin = 0.917, Tmax = 0.934 | Rint = 0.081 |
6226 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 1 restraint |
wR(F2) = 0.197 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.84 e Å−3 |
2743 reflections | Δρmin = −0.26 e Å−3 |
172 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 | ||
P1 | 0.42512 (4) | 0.27894 (9) | 0.24958 (6) | 0.0338 (3) | |
B1 | 0.43839 (18) | 0.5863 (4) | 0.2987 (3) | 0.0430 (10) | |
H1 | 0.3976 | 0.5852 | 0.3308 | 0.052* | |
B2 | 0.42621 (18) | 0.5876 (4) | 0.1819 (3) | 0.0449 (10) | |
H2 | 0.3780 | 0.5879 | 0.1379 | 0.054* | |
B3 | 0.49093 (16) | 0.4982 (4) | 0.1542 (3) | 0.0369 (9) | |
H3 | 0.4852 | 0.4392 | 0.0923 | 0.044* | |
B4 | 0.4907 (2) | 0.6734 (4) | 0.1540 (3) | 0.0507 (11) | |
H4 | 0.4848 | 0.7297 | 0.0909 | 0.061* | |
B5 | 0.4581 (2) | 0.7292 (4) | 0.2444 (3) | 0.0533 (12) | |
H5 | 0.4310 | 0.8228 | 0.2410 | 0.064* | |
C1 | 0.45992 (3) | 0.4513 (3) | 0.2439 (2) | 0.0322 (7) | |
C2 | 0.34879 (14) | 0.3209 (4) | 0.2810 (2) | 0.0376 (8) | |
H2A | 0.3332 | 0.4063 | 0.2534 | 0.045* | |
C3 | 0.29691 (16) | 0.2158 (4) | 0.2520 (2) | 0.0491 (10) | |
H3A | 0.2880 | 0.2056 | 0.1872 | 0.059* | |
H3B | 0.3121 | 0.1308 | 0.2788 | 0.059* | |
C4 | 0.23611 (17) | 0.2539 (5) | 0.2798 (3) | 0.0585 (12) | |
H4A | 0.2048 | 0.1837 | 0.2621 | 0.070* | |
H4B | 0.2189 | 0.3346 | 0.2485 | 0.070* | |
C5 | 0.24694 (19) | 0.2765 (5) | 0.3802 (3) | 0.0596 (11) | |
H5A | 0.2079 | 0.3091 | 0.3943 | 0.071* | |
H5B | 0.2581 | 0.1928 | 0.4116 | 0.071* | |
C6 | 0.30009 (18) | 0.3768 (4) | 0.4113 (3) | 0.0579 (11) | |
H6A | 0.3089 | 0.3847 | 0.4762 | 0.070* | |
H6B | 0.2866 | 0.4634 | 0.3858 | 0.070* | |
C7 | 0.36042 (16) | 0.3344 (4) | 0.3831 (2) | 0.0469 (9) | |
H7A | 0.3750 | 0.2497 | 0.4110 | 0.056* | |
H7B | 0.3937 | 0.3998 | 0.4040 | 0.056* | |
C8 | 0.40569 (16) | 0.2213 (4) | 0.1319 (2) | 0.0411 (8) | |
H8 | 0.4456 | 0.2351 | 0.1124 | 0.049* | |
C9 | 0.35584 (16) | 0.2903 (4) | 0.0595 (2) | 0.0421 (9) | |
H9A | 0.3146 | 0.2842 | 0.0749 | 0.050* | |
H9B | 0.3667 | 0.3839 | 0.0579 | 0.050* | |
C10 | 0.3510 (3) | 0.2312 (5) | −0.0312 (3) | 0.0753 (14) | |
H10A | 0.3147 | 0.2705 | −0.0727 | 0.090* | |
H10B | 0.3891 | 0.2541 | −0.0518 | 0.090* | |
C11 | 0.3436 (3) | 0.0868 (6) | −0.0332 (3) | 0.104 (2) | |
H11A | 0.3444 | 0.0544 | −0.0927 | 0.124* | |
H11B | 0.3024 | 0.0642 | −0.0216 | 0.124* | |
C12 | 0.3957 (3) | 0.0175 (5) | 0.0354 (3) | 0.0798 (15) | |
H12A | 0.4366 | 0.0311 | 0.0203 | 0.096* | |
H12B | 0.3873 | −0.0775 | 0.0346 | 0.096* | |
C13 | 0.3979 (2) | 0.0735 (4) | 0.1297 (3) | 0.0677 (12) | |
H13A | 0.3588 | 0.0504 | 0.1475 | 0.081* | |
H13B | 0.4333 | 0.0333 | 0.1725 | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0271 (4) | 0.0393 (5) | 0.0346 (5) | −0.0027 (3) | 0.0062 (3) | 0.0053 (4) |
B1 | 0.0341 (19) | 0.043 (2) | 0.055 (3) | 0.0033 (16) | 0.0179 (17) | −0.006 (2) |
B2 | 0.0306 (19) | 0.047 (2) | 0.059 (3) | 0.0054 (17) | 0.0147 (17) | 0.013 (2) |
B3 | 0.0304 (17) | 0.043 (2) | 0.040 (2) | 0.0035 (16) | 0.0118 (15) | 0.0096 (17) |
B4 | 0.045 (2) | 0.041 (2) | 0.070 (3) | 0.0025 (19) | 0.022 (2) | 0.015 (2) |
B5 | 0.046 (2) | 0.040 (2) | 0.079 (4) | 0.0055 (19) | 0.026 (2) | 0.001 (2) |
C1 | 0.0214 (15) | 0.0375 (18) | 0.0391 (19) | −0.0004 (13) | 0.0103 (12) | 0.0026 (14) |
C2 | 0.0266 (15) | 0.052 (2) | 0.0353 (19) | −0.0063 (14) | 0.0096 (13) | 0.0050 (16) |
C3 | 0.0410 (19) | 0.069 (3) | 0.040 (2) | −0.0186 (18) | 0.0134 (15) | 0.0007 (18) |
C4 | 0.0346 (19) | 0.093 (3) | 0.051 (3) | −0.0203 (19) | 0.0150 (17) | −0.003 (2) |
C5 | 0.048 (2) | 0.081 (3) | 0.058 (3) | −0.015 (2) | 0.0298 (18) | −0.003 (2) |
C6 | 0.059 (2) | 0.075 (3) | 0.046 (2) | −0.016 (2) | 0.0254 (18) | −0.008 (2) |
C7 | 0.0398 (18) | 0.062 (2) | 0.038 (2) | −0.0123 (17) | 0.0089 (15) | 0.0043 (18) |
C8 | 0.0354 (17) | 0.048 (2) | 0.040 (2) | 0.0072 (15) | 0.0083 (14) | 0.0042 (16) |
C9 | 0.0398 (18) | 0.049 (2) | 0.036 (2) | −0.0035 (16) | 0.0053 (14) | 0.0078 (16) |
C10 | 0.091 (3) | 0.082 (3) | 0.047 (3) | 0.007 (3) | 0.003 (2) | −0.003 (2) |
C11 | 0.157 (6) | 0.081 (4) | 0.055 (3) | −0.005 (4) | −0.013 (3) | −0.018 (3) |
C12 | 0.111 (4) | 0.056 (3) | 0.066 (3) | 0.007 (3) | 0.007 (3) | −0.015 (2) |
C13 | 0.076 (3) | 0.054 (3) | 0.071 (3) | −0.004 (2) | 0.012 (2) | −0.003 (2) |
P1—C8 | 1.845 (4) | C3—C4 | 1.514 (5) |
P1—C2 | 1.861 (3) | C3—H3A | 0.9700 |
P1—C1 | 1.894 (3) | C3—H3B | 0.9700 |
B1—C1 | 1.712 (5) | C4—C5 | 1.517 (6) |
B1—B2 | 1.747 (6) | C4—H4A | 0.9700 |
B1—B5 | 1.757 (6) | C4—H4B | 0.9700 |
B1—B4i | 1.762 (6) | C5—C6 | 1.516 (5) |
B1—B3i | 1.764 (5) | C5—H5A | 0.9700 |
B1—H1 | 1.1000 | C5—H5B | 0.9700 |
B2—C1 | 1.727 (5) | C6—C7 | 1.519 (5) |
B2—B5 | 1.762 (6) | C6—H6A | 0.9700 |
B2—B4 | 1.766 (6) | C6—H6B | 0.9700 |
B2—B3 | 1.786 (5) | C7—H7A | 0.9700 |
B2—H2 | 1.1000 | C7—H7B | 0.9700 |
B3—C1 | 1.722 (5) | C8—C13 | 1.493 (6) |
B3—C1i | 1.737 (5) | C8—C9 | 1.521 (5) |
B3—B4 | 1.758 (6) | C8—H8 | 0.9800 |
B3—B1i | 1.764 (5) | C9—C10 | 1.491 (6) |
B3—H3 | 1.1000 | C9—H9A | 0.9700 |
B4—B1i | 1.762 (6) | C9—H9B | 0.9700 |
B4—B5i | 1.778 (7) | C10—C11 | 1.458 (7) |
B4—B5 | 1.779 (7) | C10—H10A | 0.9700 |
B4—H4 | 1.1000 | C10—H10B | 0.9700 |
B5—B5i | 1.771 (8) | C11—C12 | 1.517 (7) |
B5—B4i | 1.778 (7) | C11—H11A | 0.9700 |
B5—H5 | 1.1000 | C11—H11B | 0.9700 |
C1—C1i | 1.6911 (10) | C12—C13 | 1.539 (6) |
C1—B3i | 1.737 (5) | C12—H12A | 0.9700 |
C2—C3 | 1.526 (5) | C12—H12B | 0.9700 |
C2—C7 | 1.530 (5) | C13—H13A | 0.9700 |
C2—H2A | 0.9800 | C13—H13B | 0.9700 |
C8—P1—C2 | 107.84 (15) | B3—C1—B2 | 62.4 (2) |
C8—P1—C1 | 104.18 (15) | C1i—C1—B3i | 60.30 (19) |
C2—P1—C1 | 100.73 (13) | B1—C1—B3i | 61.5 (2) |
C1—B1—B2 | 59.9 (2) | B3—C1—B3i | 112.0 (2) |
C1—B1—B5 | 107.0 (3) | B2—C1—B3i | 111.8 (3) |
B2—B1—B5 | 60.4 (2) | C1i—C1—P1 | 113.48 (5) |
C1—B1—B4i | 106.8 (2) | B1—C1—P1 | 123.10 (18) |
B2—B1—B4i | 109.3 (3) | B3—C1—P1 | 121.0 (2) |
B5—B1—B4i | 60.7 (3) | B2—C1—P1 | 128.88 (17) |
C1—B1—B3i | 59.93 (19) | B3i—C1—P1 | 111.8 (2) |
B2—B1—B3i | 109.6 (3) | C3—C2—C7 | 107.3 (3) |
B5—B1—B3i | 108.9 (3) | C3—C2—P1 | 113.4 (3) |
B4i—B1—B3i | 59.8 (2) | C7—C2—P1 | 109.6 (2) |
C1—B1—H1 | 122.9 | C3—C2—H2A | 108.8 |
B2—B1—H1 | 120.6 | C7—C2—H2A | 108.8 |
B5—B1—H1 | 121.5 | P1—C2—H2A | 108.8 |
B4i—B1—H1 | 121.7 | C4—C3—C2 | 111.4 (3) |
B3i—B1—H1 | 121.0 | C4—C3—H3A | 109.4 |
C1—B2—B1 | 59.1 (2) | C2—C3—H3A | 109.4 |
C1—B2—B5 | 106.1 (3) | C4—C3—H3B | 109.4 |
B1—B2—B5 | 60.1 (2) | C2—C3—H3B | 109.4 |
C1—B2—B4 | 105.3 (2) | H3A—C3—H3B | 108.0 |
B1—B2—B4 | 108.0 (3) | C3—C4—C5 | 112.3 (3) |
B5—B2—B4 | 60.5 (3) | C3—C4—H4A | 109.1 |
C1—B2—B3 | 58.67 (19) | C5—C4—H4A | 109.1 |
B1—B2—B3 | 107.2 (3) | C3—C4—H4B | 109.1 |
B5—B2—B3 | 107.8 (3) | C5—C4—H4B | 109.1 |
B4—B2—B3 | 59.3 (2) | H4A—C4—H4B | 107.9 |
C1—B2—H2 | 123.9 | C6—C5—C4 | 110.4 (3) |
B1—B2—H2 | 121.7 | C6—C5—H5A | 109.6 |
B5—B2—H2 | 121.7 | C4—C5—H5A | 109.6 |
B4—B2—H2 | 122.3 | C6—C5—H5B | 109.6 |
B3—B2—H2 | 122.3 | C4—C5—H5B | 109.6 |
C1—B3—C1i | 58.54 (13) | H5A—C5—H5B | 108.1 |
C1—B3—B4 | 105.9 (3) | C5—C6—C7 | 110.9 (3) |
C1i—B3—B4 | 105.9 (3) | C5—C6—H6A | 109.5 |
C1—B3—B1i | 105.4 (3) | C7—C6—H6A | 109.5 |
C1i—B3—B1i | 58.6 (2) | C5—C6—H6B | 109.5 |
B4—B3—B1i | 60.1 (2) | C7—C6—H6B | 109.5 |
C1—B3—B2 | 59.0 (2) | H6A—C6—H6B | 108.1 |
C1i—B3—B2 | 105.7 (3) | C6—C7—C2 | 111.3 (3) |
B4—B3—B2 | 59.8 (2) | C6—C7—H7A | 109.4 |
B1i—B3—B2 | 107.3 (3) | C2—C7—H7A | 109.4 |
C1—B3—H3 | 123.5 | C6—C7—H7B | 109.4 |
C1i—B3—H3 | 123.5 | C2—C7—H7B | 109.4 |
B4—B3—H3 | 122.4 | H7A—C7—H7B | 108.0 |
B1i—B3—H3 | 122.5 | C13—C8—C9 | 112.3 (3) |
B2—B3—H3 | 122.3 | C13—C8—P1 | 109.4 (3) |
B3—B4—B1i | 60.1 (2) | C9—C8—P1 | 122.2 (3) |
B3—B4—B2 | 60.9 (2) | C13—C8—H8 | 103.6 |
B1i—B4—B2 | 108.2 (3) | C9—C8—H8 | 103.6 |
B3—B4—B5i | 108.2 (3) | P1—C8—H8 | 103.6 |
B1i—B4—B5i | 59.5 (2) | C10—C9—C8 | 112.7 (3) |
B2—B4—B5i | 107.8 (3) | C10—C9—H9A | 109.1 |
B3—B4—B5 | 108.3 (3) | C8—C9—H9A | 109.1 |
B1i—B4—B5 | 107.1 (3) | C10—C9—H9B | 109.1 |
B2—B4—B5 | 59.6 (3) | C8—C9—H9B | 109.1 |
B5i—B4—B5 | 59.7 (3) | H9A—C9—H9B | 107.8 |
B3—B4—H4 | 121.1 | C11—C10—C9 | 113.5 (4) |
B1i—B4—H4 | 122.1 | C11—C10—H10A | 108.9 |
B2—B4—H4 | 121.5 | C9—C10—H10A | 108.9 |
B5i—B4—H4 | 122.0 | C11—C10—H10B | 108.9 |
B5—B4—H4 | 122.2 | C9—C10—H10B | 108.9 |
B1—B5—B2 | 59.5 (2) | H10A—C10—H10B | 107.7 |
B1—B5—B5i | 107.7 (3) | C10—C11—C12 | 112.5 (4) |
B2—B5—B5i | 108.3 (3) | C10—C11—H11A | 109.1 |
B1—B5—B4i | 59.8 (2) | C12—C11—H11A | 109.1 |
B2—B5—B4i | 107.9 (3) | C10—C11—H11B | 109.1 |
B5i—B5—B4i | 60.2 (3) | C12—C11—H11B | 109.1 |
B1—B5—B4 | 106.9 (3) | H11A—C11—H11B | 107.8 |
B2—B5—B4 | 59.8 (2) | C11—C12—C13 | 110.0 (4) |
B5i—B5—B4 | 60.1 (3) | C11—C12—H12A | 109.7 |
B4i—B5—B4 | 107.8 (3) | C13—C12—H12A | 109.7 |
B1—B5—H5 | 122.4 | C11—C12—H12B | 109.7 |
B2—B5—H5 | 121.7 | C13—C12—H12B | 109.7 |
B5i—B5—H5 | 121.4 | H12A—C12—H12B | 108.2 |
B4i—B5—H5 | 121.7 | C8—C13—C12 | 111.3 (4) |
B4—B5—H5 | 122.1 | C8—C13—H13A | 109.4 |
C1i—C1—B1 | 109.19 (19) | C12—C13—H13A | 109.4 |
C1i—C1—B3 | 61.16 (19) | C8—C13—H13B | 109.4 |
B1—C1—B3 | 111.8 (3) | C12—C13—H13B | 109.4 |
C1i—C1—B2 | 110.50 (19) | H13A—C13—H13B | 108.0 |
B1—C1—B2 | 61.0 (2) |
Symmetry code: (i) −x+1, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C26H54B10P2 |
Mr | 536.73 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 21.507 (2), 10.0350 (14), 15.2976 (18) |
β (°) | 103.196 (2) |
V (Å3) | 3214.4 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.15 |
Crystal size (mm) | 0.58 × 0.57 × 0.46 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.917, 0.934 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6226, 2743, 1814 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.197, 1.00 |
No. of reflections | 2743 |
No. of parameters | 172 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.84, −0.26 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
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The structure of 1,2-(PPh2)-1,2-C2B10H10 (Zhang et al., 2006) has recently been reported and was synthesized by the method of Alexander & Schroeder (1963). In addition, 1,2-(PiPr2)2-1,2-C2B10H10 was synthesized and characterized by Kivekäs et al. (1995). Since then, many complexes containing the above two lignads have been reported. We are interested in phosphine derivatives of 1,2-dicarba-closo-dodecaborane. In this paper, we report the structure of 1,2-bis(dicyclohexylphosphino)-1,2-dicarba-closo-dodecaborane.
As shown in Fig. 1, the molecular structure of the title compound has crystallographic twofold rotation symmetry. The P atom of dicyclohexylphosphine group is bonded to C1. The P—C1 distance is 1.894 (3) Å, which is agreement well with the corresponding distance 1.894 (3) Å in 1,2-(PiPr2)2-1,2-C2B10H10 and 1.885 Å in 1,2-(PPh2)-1,2-C2B10H10. The P—C1—C1i angle [symmetry code (i): 1 - x, y, 1/2 - z] in 1,2-(PCycl2)-1,2-C2B10H10 is 113.48 (5)°. The corresponding angles in 1,2-(PPh2)-1,2-C2B10H10 (Zhang et al., 2006) and 1,2-(PiPr2)2-1,2-C2B10H10 (Kivekäs et al., 1995) are 116.6 (2),111.07 (19)° and 112.9 (2),112.3 (1)° respectively. The two phosphorus and two cage C atoms are almost coplanar with the torsion angle 10.9 (4)°, which is samller than that of 12.1 (2)° for 1,2-(PiPr2)2-1,2-C2B10H10 (Kivekäs et al., 1995), and almost equal to that of 10.6 (3)° for 1,2-(PPh2)-1,2-C2B10H10 (Zhang et al., 2006).