Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043164/lh2495sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043164/lh2495Isup2.hkl |
CCDC reference: 663575
Equimolar quantities of Mo(CO)6, triphenylphosphine and 2,2-bipyridine were refluxed in toluene under an N2 atmosphere for seven hours. Air-stable black blocks of (I) were recovered by vacuum filtration and rinsing with light petroleum ether in 93% yield based on Mo(CO)6. When the crystals of (I) are smeared on a glass slide, a very deep orange colour is apparent.
The hydrogen atoms were geometrically placed (C—H = 0.93 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).
The title compound,(I), Mo(CO)3(C18H15P)(C10H8N2), is an example of a trisubstituted group-6 metal hexacarbonyl (Howie & McQuillan, 1986). The related tricarbonyl-triphenylphosphine-1,10-phenanthroline-molybdenum(0), (II), was described in the preceding paper (Muir et al., 2007).
The three remaining carbonyl groups atached to the Mo atom in (I) form one face of the distorted MoC3N2P octahedron. Otherwise, all the bond lengths and angles in (I) (Fig. 1) may be regarded as normal (Allen et al., 1987). The diehdral angles for the phenyl rings for the triphenylphosphine molecule are C14—C19/C20—C25 = 86.93 (11)°, C14—C19/C26—C31 = 77.16 (12)°, and C20—C25/C26—C31 = 63.38 (12)°. The N—Mo—N bite angle for the 2,2-bipyridyl (bipy) molecule is 71.89 (6)° and the twist angle of the N1/C4—C8 and N2/C9—C12 bipy rings is 6.57 (12)°.
There is a slight distinction between the shorter Mo1—C2 and Mo1—C3 bond lengths trans to the bipy N atoms and the longer Mo1—C1 bond, which is trans to the P atom. A similar pattern was seen in (II) and the possible origin of this effect is discussed in the previous paper (Muir et al., 2007).
In the crystal of (I), a short, near linear, C—H···O interaction arising from a bipy C—H grouping may help to establish the packing.
For a related structure, see: Muir et al. (2007). For background, see: Howie & McQuillan (1986). For reference structural data, see: Allen et al. (1987).
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. View of the molecular structure of (I) showing 50% displacement ellipsoids (H atoms omitted for clarity). |
[Mo(CO)3(C18H15P)(C10H8N2)] | Z = 2 |
Mr = 598.42 | F(000) = 608 |
Triclinic, P1 | Dx = 1.495 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5206 (4) Å | Cell parameters from 5346 reflections |
b = 9.3188 (4) Å | θ = 2.3–29.8° |
c = 18.4747 (8) Å | µ = 0.59 mm−1 |
α = 91.986 (1)° | T = 293 K |
β = 102.425 (1)° | Block, black |
γ = 110.762 (1)° | 0.33 × 0.30 × 0.14 mm |
V = 1329.62 (10) Å3 |
Bruker SMART 1000 CCD diffractometer | 7569 independent reflections |
Radiation source: fine-focus sealed tube | 6055 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω scans | θmax = 30.0°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −11→11 |
Tmin = 0.829, Tmax = 0.922 | k = −13→13 |
11901 measured reflections | l = −25→20 |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.069 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0326P)2] where P = (Fo2 + 2Fc2)/3 |
7569 reflections | (Δ/σ)max = 0.002 |
343 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
[Mo(CO)3(C18H15P)(C10H8N2)] | γ = 110.762 (1)° |
Mr = 598.42 | V = 1329.62 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.5206 (4) Å | Mo Kα radiation |
b = 9.3188 (4) Å | µ = 0.59 mm−1 |
c = 18.4747 (8) Å | T = 293 K |
α = 91.986 (1)° | 0.33 × 0.30 × 0.14 mm |
β = 102.425 (1)° |
Bruker SMART 1000 CCD diffractometer | 7569 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | 6055 reflections with I > 2σ(I) |
Tmin = 0.829, Tmax = 0.922 | Rint = 0.017 |
11901 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.069 | H-atom parameters constrained |
S = 0.96 | Δρmax = 0.39 e Å−3 |
7569 reflections | Δρmin = −0.40 e Å−3 |
343 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 | ||
Mo1 | 0.54639 (2) | 0.201182 (18) | 0.340276 (9) | 0.03355 (5) | |
C1 | 0.7158 (3) | 0.1373 (3) | 0.30803 (11) | 0.0498 (5) | |
C2 | 0.4073 (3) | −0.0166 (2) | 0.33589 (11) | 0.0426 (4) | |
C3 | 0.6642 (3) | 0.1705 (2) | 0.43863 (12) | 0.0459 (5) | |
O1 | 0.8222 (2) | 0.0975 (2) | 0.29381 (10) | 0.0814 (6) | |
O2 | 0.3293 (2) | −0.14685 (17) | 0.33732 (9) | 0.0657 (4) | |
O3 | 0.7344 (2) | 0.1385 (2) | 0.49254 (9) | 0.0794 (5) | |
P1 | 0.38541 (6) | 0.21208 (5) | 0.20506 (3) | 0.03306 (10) | |
C4 | 0.2377 (3) | 0.2269 (3) | 0.40571 (12) | 0.0553 (6) | |
H4 | 0.2012 | 0.1197 | 0.4007 | 0.066* | |
C5 | 0.1404 (3) | 0.2959 (4) | 0.43382 (13) | 0.0729 (8) | |
H5 | 0.0407 | 0.2359 | 0.4475 | 0.088* | |
C6 | 0.1923 (4) | 0.4526 (4) | 0.44115 (14) | 0.0800 (9) | |
H6 | 0.1280 | 0.5009 | 0.4596 | 0.096* | |
C7 | 0.3398 (4) | 0.5385 (3) | 0.42112 (13) | 0.0671 (7) | |
H7 | 0.3761 | 0.6457 | 0.4257 | 0.080* | |
C8 | 0.4360 (3) | 0.4648 (2) | 0.39371 (10) | 0.0458 (5) | |
C9 | 0.6016 (3) | 0.5479 (2) | 0.37634 (11) | 0.0491 (5) | |
C10 | 0.6801 (4) | 0.7096 (3) | 0.38419 (14) | 0.0729 (8) | |
H10 | 0.6236 | 0.7706 | 0.3987 | 0.087* | |
C11 | 0.8389 (5) | 0.7766 (3) | 0.37055 (18) | 0.0955 (11) | |
H11 | 0.8924 | 0.8837 | 0.3766 | 0.115* | |
C12 | 0.9193 (4) | 0.6879 (4) | 0.34825 (18) | 0.0913 (11) | |
H12 | 1.0284 | 0.7329 | 0.3391 | 0.110* | |
C13 | 0.8366 (3) | 0.5293 (3) | 0.33933 (14) | 0.0655 (7) | |
H13 | 0.8914 | 0.4688 | 0.3229 | 0.079* | |
C14 | 0.1842 (2) | 0.0461 (2) | 0.16510 (10) | 0.0349 (4) | |
C15 | 0.0669 (3) | −0.0116 (2) | 0.20944 (11) | 0.0451 (5) | |
H15 | 0.0935 | 0.0329 | 0.2585 | 0.054* | |
C16 | −0.0870 (3) | −0.1329 (3) | 0.18131 (13) | 0.0541 (5) | |
H16 | −0.1649 | −0.1680 | 0.2111 | 0.065* | |
C17 | −0.1271 (3) | −0.2033 (3) | 0.10943 (13) | 0.0559 (6) | |
H17 | −0.2302 | −0.2873 | 0.0911 | 0.067* | |
C18 | −0.0135 (3) | −0.1486 (3) | 0.06497 (12) | 0.0542 (5) | |
H18 | −0.0401 | −0.1951 | 0.0163 | 0.065* | |
C19 | 0.1399 (3) | −0.0247 (2) | 0.09255 (11) | 0.0449 (5) | |
H19 | 0.2151 | 0.0120 | 0.0618 | 0.054* | |
C20 | 0.5032 (2) | 0.2250 (2) | 0.13138 (10) | 0.0364 (4) | |
C21 | 0.5974 (3) | 0.1310 (2) | 0.12924 (11) | 0.0468 (5) | |
H21 | 0.6019 | 0.0647 | 0.1655 | 0.056* | |
C22 | 0.6851 (3) | 0.1345 (3) | 0.07362 (12) | 0.0561 (6) | |
H22 | 0.7469 | 0.0701 | 0.0726 | 0.067* | |
C23 | 0.6810 (3) | 0.2324 (3) | 0.02036 (12) | 0.0575 (6) | |
H23 | 0.7421 | 0.2363 | −0.0161 | 0.069* | |
C24 | 0.5870 (3) | 0.3242 (3) | 0.02087 (13) | 0.0634 (7) | |
H24 | 0.5829 | 0.3897 | −0.0157 | 0.076* | |
C25 | 0.4971 (3) | 0.3204 (3) | 0.07585 (12) | 0.0540 (6) | |
H25 | 0.4323 | 0.3825 | 0.0753 | 0.065* | |
C26 | 0.3143 (3) | 0.3767 (2) | 0.19348 (10) | 0.0394 (4) | |
C27 | 0.4389 (3) | 0.5245 (2) | 0.20278 (11) | 0.0466 (5) | |
H27 | 0.5553 | 0.5378 | 0.2130 | 0.056* | |
C28 | 0.3925 (4) | 0.6529 (3) | 0.19702 (13) | 0.0599 (6) | |
H28 | 0.4774 | 0.7513 | 0.2028 | 0.072* | |
C29 | 0.2216 (4) | 0.6345 (3) | 0.18279 (15) | 0.0721 (8) | |
H29 | 0.1903 | 0.7205 | 0.1789 | 0.087* | |
C30 | 0.0972 (4) | 0.4900 (3) | 0.17433 (17) | 0.0800 (8) | |
H30 | −0.0186 | 0.4783 | 0.1650 | 0.096* | |
C31 | 0.1417 (3) | 0.3593 (3) | 0.17956 (14) | 0.0612 (6) | |
H31 | 0.0560 | 0.2614 | 0.1737 | 0.073* | |
N1 | 0.3831 (2) | 0.30873 (19) | 0.38523 (8) | 0.0396 (3) | |
N2 | 0.6812 (2) | 0.45842 (19) | 0.35315 (9) | 0.0450 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mo1 | 0.03453 (9) | 0.03719 (9) | 0.03219 (9) | 0.01658 (7) | 0.00891 (6) | 0.00554 (6) |
C1 | 0.0499 (12) | 0.0666 (14) | 0.0390 (11) | 0.0317 (11) | 0.0060 (9) | 0.0042 (10) |
C2 | 0.0471 (12) | 0.0456 (11) | 0.0391 (11) | 0.0232 (10) | 0.0086 (9) | 0.0053 (8) |
C3 | 0.0483 (12) | 0.0518 (12) | 0.0403 (11) | 0.0204 (10) | 0.0128 (9) | 0.0067 (9) |
O1 | 0.0698 (12) | 0.1285 (17) | 0.0707 (12) | 0.0680 (13) | 0.0160 (9) | −0.0038 (11) |
O2 | 0.0753 (12) | 0.0396 (9) | 0.0763 (12) | 0.0147 (8) | 0.0170 (9) | 0.0097 (8) |
O3 | 0.0828 (13) | 0.1166 (16) | 0.0461 (10) | 0.0509 (12) | 0.0045 (9) | 0.0241 (10) |
P1 | 0.0364 (3) | 0.0349 (2) | 0.0325 (2) | 0.0181 (2) | 0.00932 (19) | 0.00561 (18) |
C4 | 0.0414 (12) | 0.0751 (16) | 0.0453 (12) | 0.0173 (11) | 0.0118 (9) | −0.0063 (10) |
C5 | 0.0466 (14) | 0.130 (3) | 0.0466 (14) | 0.0390 (16) | 0.0114 (10) | −0.0067 (14) |
C6 | 0.089 (2) | 0.132 (3) | 0.0500 (15) | 0.082 (2) | 0.0119 (14) | −0.0012 (16) |
C7 | 0.100 (2) | 0.0775 (17) | 0.0453 (13) | 0.0639 (17) | 0.0082 (13) | 0.0024 (11) |
C8 | 0.0598 (13) | 0.0510 (12) | 0.0309 (10) | 0.0322 (11) | 0.0004 (9) | 0.0016 (8) |
C9 | 0.0631 (14) | 0.0377 (10) | 0.0377 (11) | 0.0185 (10) | −0.0054 (9) | 0.0045 (8) |
C10 | 0.096 (2) | 0.0420 (13) | 0.0619 (16) | 0.0206 (14) | −0.0105 (14) | 0.0049 (11) |
C11 | 0.100 (3) | 0.0490 (16) | 0.091 (2) | −0.0051 (17) | −0.0167 (18) | 0.0255 (15) |
C12 | 0.0578 (18) | 0.078 (2) | 0.102 (2) | −0.0075 (16) | −0.0034 (16) | 0.0469 (18) |
C13 | 0.0440 (13) | 0.0688 (16) | 0.0720 (16) | 0.0091 (12) | 0.0066 (11) | 0.0324 (13) |
C14 | 0.0382 (10) | 0.0347 (9) | 0.0358 (10) | 0.0189 (8) | 0.0076 (7) | 0.0066 (7) |
C15 | 0.0415 (11) | 0.0546 (12) | 0.0397 (11) | 0.0179 (10) | 0.0108 (8) | 0.0046 (9) |
C16 | 0.0426 (12) | 0.0646 (14) | 0.0543 (14) | 0.0164 (11) | 0.0149 (10) | 0.0135 (11) |
C17 | 0.0424 (13) | 0.0499 (13) | 0.0620 (15) | 0.0092 (11) | −0.0005 (10) | 0.0030 (11) |
C18 | 0.0549 (14) | 0.0523 (13) | 0.0463 (13) | 0.0172 (11) | 0.0007 (10) | −0.0072 (10) |
C19 | 0.0495 (12) | 0.0471 (11) | 0.0386 (11) | 0.0190 (10) | 0.0103 (9) | 0.0030 (8) |
C20 | 0.0390 (10) | 0.0384 (10) | 0.0347 (10) | 0.0170 (8) | 0.0104 (8) | 0.0059 (7) |
C21 | 0.0574 (13) | 0.0531 (12) | 0.0409 (11) | 0.0315 (11) | 0.0147 (9) | 0.0094 (9) |
C22 | 0.0615 (14) | 0.0738 (16) | 0.0484 (13) | 0.0417 (13) | 0.0171 (11) | 0.0036 (11) |
C23 | 0.0613 (15) | 0.0683 (15) | 0.0510 (14) | 0.0245 (13) | 0.0296 (11) | 0.0064 (11) |
C24 | 0.094 (2) | 0.0621 (14) | 0.0551 (14) | 0.0378 (14) | 0.0419 (14) | 0.0275 (11) |
C25 | 0.0751 (16) | 0.0580 (13) | 0.0508 (13) | 0.0417 (13) | 0.0285 (11) | 0.0224 (10) |
C26 | 0.0496 (12) | 0.0407 (10) | 0.0345 (10) | 0.0261 (9) | 0.0079 (8) | 0.0037 (8) |
C27 | 0.0559 (13) | 0.0407 (11) | 0.0455 (12) | 0.0236 (10) | 0.0066 (9) | 0.0081 (9) |
C28 | 0.0847 (19) | 0.0409 (12) | 0.0539 (14) | 0.0300 (12) | 0.0051 (12) | 0.0056 (10) |
C29 | 0.094 (2) | 0.0574 (15) | 0.0753 (18) | 0.0540 (16) | −0.0008 (14) | −0.0009 (12) |
C30 | 0.0695 (18) | 0.079 (2) | 0.108 (2) | 0.0565 (17) | 0.0075 (16) | 0.0021 (16) |
C31 | 0.0497 (13) | 0.0494 (13) | 0.0879 (18) | 0.0281 (11) | 0.0078 (12) | 0.0008 (12) |
N1 | 0.0387 (9) | 0.0464 (9) | 0.0343 (8) | 0.0182 (8) | 0.0068 (7) | −0.0012 (7) |
N2 | 0.0391 (9) | 0.0441 (9) | 0.0445 (10) | 0.0105 (8) | 0.0028 (7) | 0.0137 (7) |
Mo1—C1 | 1.936 (2) | C14—C19 | 1.385 (3) |
Mo1—C2 | 1.942 (2) | C14—C15 | 1.400 (2) |
Mo1—C3 | 1.961 (2) | C15—C16 | 1.372 (3) |
Mo1—N2 | 2.2390 (16) | C15—H15 | 0.9300 |
Mo1—N1 | 2.2491 (15) | C16—C17 | 1.377 (3) |
Mo1—P1 | 2.6026 (5) | C16—H16 | 0.9300 |
C1—O1 | 1.167 (2) | C17—C18 | 1.376 (3) |
C2—O2 | 1.163 (2) | C17—H17 | 0.9300 |
C3—O3 | 1.153 (2) | C18—C19 | 1.380 (3) |
P1—C14 | 1.8364 (19) | C18—H18 | 0.9300 |
P1—C20 | 1.8409 (17) | C19—H19 | 0.9300 |
P1—C26 | 1.8413 (18) | C20—C25 | 1.385 (3) |
C4—N1 | 1.346 (2) | C20—C21 | 1.387 (3) |
C4—C5 | 1.382 (3) | C21—C22 | 1.390 (3) |
C4—H4 | 0.9300 | C21—H21 | 0.9300 |
C5—C6 | 1.360 (4) | C22—C23 | 1.368 (3) |
C5—H5 | 0.9300 | C22—H22 | 0.9300 |
C6—C7 | 1.365 (4) | C23—C24 | 1.365 (3) |
C6—H6 | 0.9300 | C23—H23 | 0.9300 |
C7—C8 | 1.398 (3) | C24—C25 | 1.392 (3) |
C7—H7 | 0.9300 | C24—H24 | 0.9300 |
C8—N1 | 1.354 (2) | C25—H25 | 0.9300 |
C8—C9 | 1.460 (3) | C26—C31 | 1.386 (3) |
C9—N2 | 1.356 (3) | C26—C27 | 1.387 (3) |
C9—C10 | 1.403 (3) | C27—C28 | 1.387 (3) |
C10—C11 | 1.358 (4) | C27—H27 | 0.9300 |
C10—H10 | 0.9300 | C28—C29 | 1.369 (4) |
C11—C12 | 1.349 (5) | C28—H28 | 0.9300 |
C11—H11 | 0.9300 | C29—C30 | 1.365 (4) |
C12—C13 | 1.379 (4) | C29—H29 | 0.9300 |
C12—H12 | 0.9300 | C30—C31 | 1.398 (3) |
C13—N2 | 1.339 (3) | C30—H30 | 0.9300 |
C13—H13 | 0.9300 | C31—H31 | 0.9300 |
C1—Mo1—C2 | 87.51 (9) | C16—C15—C14 | 120.81 (19) |
C1—Mo1—C3 | 82.55 (8) | C16—C15—H15 | 119.6 |
C2—Mo1—C3 | 83.16 (8) | C14—C15—H15 | 119.6 |
C1—Mo1—N2 | 100.21 (8) | C15—C16—C17 | 120.59 (19) |
C2—Mo1—N2 | 172.16 (7) | C15—C16—H16 | 119.7 |
C3—Mo1—N2 | 96.37 (7) | C17—C16—H16 | 119.7 |
C1—Mo1—N1 | 171.38 (8) | C18—C17—C16 | 119.5 (2) |
C2—Mo1—N1 | 100.33 (7) | C18—C17—H17 | 120.3 |
C3—Mo1—N1 | 94.73 (7) | C16—C17—H17 | 120.3 |
N2—Mo1—N1 | 71.89 (6) | C17—C18—C19 | 120.1 (2) |
C1—Mo1—P1 | 93.91 (6) | C17—C18—H18 | 119.9 |
C2—Mo1—P1 | 91.80 (6) | C19—C18—H18 | 120.0 |
C3—Mo1—P1 | 173.94 (6) | C18—C19—C14 | 121.35 (19) |
N2—Mo1—P1 | 89.09 (4) | C18—C19—H19 | 119.3 |
N1—Mo1—P1 | 89.47 (4) | C14—C19—H19 | 119.3 |
O1—C1—Mo1 | 175.20 (18) | C25—C20—C21 | 118.05 (17) |
O2—C2—Mo1 | 176.14 (18) | C25—C20—P1 | 123.02 (14) |
O3—C3—Mo1 | 172.57 (19) | C21—C20—P1 | 118.89 (14) |
C14—P1—C20 | 101.81 (8) | C20—C21—C22 | 120.79 (19) |
C14—P1—C26 | 102.34 (9) | C20—C21—H21 | 119.6 |
C20—P1—C26 | 102.08 (8) | C22—C21—H21 | 119.6 |
C14—P1—Mo1 | 115.77 (6) | C23—C22—C21 | 120.3 (2) |
C20—P1—Mo1 | 117.49 (6) | C23—C22—H22 | 119.9 |
C26—P1—Mo1 | 115.11 (6) | C21—C22—H22 | 119.9 |
N1—C4—C5 | 122.6 (2) | C24—C23—C22 | 119.82 (19) |
N1—C4—H4 | 118.7 | C24—C23—H23 | 120.1 |
C5—C4—H4 | 118.7 | C22—C23—H23 | 120.1 |
C6—C5—C4 | 119.2 (2) | C23—C24—C25 | 120.4 (2) |
C6—C5—H5 | 120.4 | C23—C24—H24 | 119.8 |
C4—C5—H5 | 120.4 | C25—C24—H24 | 119.8 |
C5—C6—C7 | 119.4 (2) | C20—C25—C24 | 120.6 (2) |
C5—C6—H6 | 120.3 | C20—C25—H25 | 119.7 |
C7—C6—H6 | 120.3 | C24—C25—H25 | 119.7 |
C6—C7—C8 | 119.8 (2) | C31—C26—C27 | 118.67 (18) |
C6—C7—H7 | 120.1 | C31—C26—P1 | 122.59 (16) |
C8—C7—H7 | 120.1 | C27—C26—P1 | 118.66 (15) |
N1—C8—C7 | 120.9 (2) | C26—C27—C28 | 121.0 (2) |
N1—C8—C9 | 115.68 (17) | C26—C27—H27 | 119.5 |
C7—C8—C9 | 123.4 (2) | C28—C27—H27 | 119.5 |
N2—C9—C10 | 120.4 (2) | C29—C28—C27 | 119.9 (2) |
N2—C9—C8 | 115.70 (17) | C29—C28—H28 | 120.0 |
C10—C9—C8 | 123.8 (2) | C27—C28—H28 | 120.0 |
C11—C10—C9 | 119.6 (3) | C30—C29—C28 | 120.0 (2) |
C11—C10—H10 | 120.2 | C30—C29—H29 | 120.0 |
C9—C10—H10 | 120.2 | C28—C29—H29 | 120.0 |
C12—C11—C10 | 120.1 (3) | C29—C30—C31 | 120.8 (2) |
C12—C11—H11 | 119.9 | C29—C30—H30 | 119.6 |
C10—C11—H11 | 119.9 | C31—C30—H30 | 119.6 |
C11—C12—C13 | 118.7 (3) | C26—C31—C30 | 119.6 (2) |
C11—C12—H12 | 120.6 | C26—C31—H31 | 120.2 |
C13—C12—H12 | 120.6 | C30—C31—H31 | 120.2 |
N2—C13—C12 | 123.2 (3) | C4—N1—C8 | 118.09 (18) |
N2—C13—H13 | 118.4 | C4—N1—Mo1 | 123.74 (14) |
C12—C13—H13 | 118.4 | C8—N1—Mo1 | 118.15 (13) |
C19—C14—C15 | 117.63 (18) | C13—N2—C9 | 117.9 (2) |
C19—C14—P1 | 123.55 (14) | C13—N2—Mo1 | 123.65 (17) |
C15—C14—P1 | 118.82 (14) | C9—N2—Mo1 | 118.43 (13) |
C1—Mo1—P1—C14 | 101.14 (9) | C20—C21—C22—C23 | 0.6 (4) |
C2—Mo1—P1—C14 | 13.52 (8) | C21—C22—C23—C24 | −1.5 (4) |
N2—Mo1—P1—C14 | −158.69 (8) | C22—C23—C24—C25 | 0.9 (4) |
N1—Mo1—P1—C14 | −86.79 (7) | C21—C20—C25—C24 | −1.7 (3) |
C1—Mo1—P1—C20 | −19.34 (10) | P1—C20—C25—C24 | −179.15 (19) |
C2—Mo1—P1—C20 | −106.96 (9) | C23—C24—C25—C20 | 0.8 (4) |
N2—Mo1—P1—C20 | 80.83 (8) | C14—P1—C26—C31 | 17.05 (19) |
N1—Mo1—P1—C20 | 152.72 (8) | C20—P1—C26—C31 | 122.18 (18) |
C1—Mo1—P1—C26 | −139.63 (10) | Mo1—P1—C26—C31 | −109.39 (18) |
C2—Mo1—P1—C26 | 132.75 (9) | C14—P1—C26—C27 | −166.29 (15) |
N2—Mo1—P1—C26 | −39.46 (8) | C20—P1—C26—C27 | −61.16 (16) |
N1—Mo1—P1—C26 | 32.43 (8) | Mo1—P1—C26—C27 | 67.27 (15) |
N1—C4—C5—C6 | 0.1 (4) | C31—C26—C27—C28 | −1.1 (3) |
C4—C5—C6—C7 | −0.4 (4) | P1—C26—C27—C28 | −177.93 (16) |
C5—C6—C7—C8 | −0.3 (4) | C26—C27—C28—C29 | 0.7 (3) |
C6—C7—C8—N1 | 1.4 (3) | C27—C28—C29—C30 | 0.0 (4) |
C6—C7—C8—C9 | −175.2 (2) | C28—C29—C30—C31 | −0.4 (4) |
N1—C8—C9—N2 | 0.6 (3) | C27—C26—C31—C30 | 0.8 (3) |
C7—C8—C9—N2 | 177.40 (18) | P1—C26—C31—C30 | 177.4 (2) |
N1—C8—C9—C10 | −177.78 (19) | C29—C30—C31—C26 | 0.0 (4) |
C7—C8—C9—C10 | −1.0 (3) | C5—C4—N1—C8 | 0.9 (3) |
N2—C9—C10—C11 | −1.9 (3) | C5—C4—N1—Mo1 | 179.41 (17) |
C8—C9—C10—C11 | 176.4 (2) | C7—C8—N1—C4 | −1.7 (3) |
C9—C10—C11—C12 | 1.2 (4) | C9—C8—N1—C4 | 175.21 (17) |
C10—C11—C12—C13 | 0.4 (5) | C7—C8—N1—Mo1 | 179.76 (15) |
C11—C12—C13—N2 | −1.3 (4) | C9—C8—N1—Mo1 | −3.4 (2) |
C20—P1—C14—C19 | −8.21 (18) | C2—Mo1—N1—C4 | 3.97 (17) |
C26—P1—C14—C19 | 97.13 (17) | C3—Mo1—N1—C4 | −79.92 (17) |
Mo1—P1—C14—C19 | −136.86 (14) | N2—Mo1—N1—C4 | −175.09 (17) |
C20—P1—C14—C15 | 172.80 (15) | P1—Mo1—N1—C4 | 95.70 (16) |
C26—P1—C14—C15 | −81.86 (16) | C2—Mo1—N1—C8 | −177.54 (14) |
Mo1—P1—C14—C15 | 44.15 (16) | C3—Mo1—N1—C8 | 98.57 (15) |
C19—C14—C15—C16 | −0.7 (3) | N2—Mo1—N1—C8 | 3.41 (13) |
P1—C14—C15—C16 | 178.40 (16) | P1—Mo1—N1—C8 | −85.81 (13) |
C14—C15—C16—C17 | 1.8 (3) | C12—C13—N2—C9 | 0.6 (3) |
C15—C16—C17—C18 | −1.7 (3) | C12—C13—N2—Mo1 | −179.26 (19) |
C16—C17—C18—C19 | 0.4 (3) | C10—C9—N2—C13 | 1.0 (3) |
C17—C18—C19—C14 | 0.7 (3) | C8—C9—N2—C13 | −177.45 (18) |
C15—C14—C19—C18 | −0.6 (3) | C10—C9—N2—Mo1 | −179.10 (16) |
P1—C14—C19—C18 | −179.59 (16) | C8—C9—N2—Mo1 | 2.4 (2) |
C14—P1—C20—C25 | 94.16 (19) | C1—Mo1—N2—C13 | 0.37 (18) |
C26—P1—C20—C25 | −11.4 (2) | C3—Mo1—N2—C13 | 83.91 (17) |
Mo1—P1—C20—C25 | −138.29 (17) | N1—Mo1—N2—C13 | 176.82 (18) |
C14—P1—C20—C21 | −83.26 (17) | P1—Mo1—N2—C13 | −93.44 (16) |
C26—P1—C20—C21 | 171.20 (17) | C1—Mo1—N2—C9 | −179.51 (14) |
Mo1—P1—C20—C21 | 44.29 (18) | C3—Mo1—N2—C9 | −95.97 (15) |
C25—C20—C21—C22 | 1.0 (3) | N1—Mo1—N2—C9 | −3.06 (13) |
P1—C20—C21—C22 | 178.58 (17) | P1—Mo1—N2—C9 | 86.68 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O2i | 0.93 | 2.41 | 3.336 (4) | 171 |
Symmetry code: (i) x+1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | [Mo(CO)3(C18H15P)(C10H8N2)] |
Mr | 598.42 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.5206 (4), 9.3188 (4), 18.4747 (8) |
α, β, γ (°) | 91.986 (1), 102.425 (1), 110.762 (1) |
V (Å3) | 1329.62 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.59 |
Crystal size (mm) | 0.33 × 0.30 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 1999) |
Tmin, Tmax | 0.829, 0.922 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11901, 7569, 6055 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.069, 0.96 |
No. of reflections | 7569 |
No. of parameters | 343 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.39, −0.40 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).
Mo1—C1 | 1.936 (2) | Mo1—N2 | 2.2390 (16) |
Mo1—C2 | 1.942 (2) | Mo1—N1 | 2.2491 (15) |
Mo1—C3 | 1.961 (2) | Mo1—P1 | 2.6026 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O2i | 0.93 | 2.41 | 3.336 (4) | 171 |
Symmetry code: (i) x+1, y+1, z. |
The title compound,(I), Mo(CO)3(C18H15P)(C10H8N2), is an example of a trisubstituted group-6 metal hexacarbonyl (Howie & McQuillan, 1986). The related tricarbonyl-triphenylphosphine-1,10-phenanthroline-molybdenum(0), (II), was described in the preceding paper (Muir et al., 2007).
The three remaining carbonyl groups atached to the Mo atom in (I) form one face of the distorted MoC3N2P octahedron. Otherwise, all the bond lengths and angles in (I) (Fig. 1) may be regarded as normal (Allen et al., 1987). The diehdral angles for the phenyl rings for the triphenylphosphine molecule are C14—C19/C20—C25 = 86.93 (11)°, C14—C19/C26—C31 = 77.16 (12)°, and C20—C25/C26—C31 = 63.38 (12)°. The N—Mo—N bite angle for the 2,2-bipyridyl (bipy) molecule is 71.89 (6)° and the twist angle of the N1/C4—C8 and N2/C9—C12 bipy rings is 6.57 (12)°.
There is a slight distinction between the shorter Mo1—C2 and Mo1—C3 bond lengths trans to the bipy N atoms and the longer Mo1—C1 bond, which is trans to the P atom. A similar pattern was seen in (II) and the possible origin of this effect is discussed in the previous paper (Muir et al., 2007).
In the crystal of (I), a short, near linear, C—H···O interaction arising from a bipy C—H grouping may help to establish the packing.