Acta Cryst. (2007). E63, m2492 [ doi:10.1107/S1600536807043176 ]
In the title compound, [Mo(CO)3(C18H15P)(C12H8N2)] or C33H23MoN2O3P, the carbonyl groups are attached to one face of the MoC3N2P octahedron. Slight differences in the Mo-C bond lengths may be interpreted in terms of back-bonding models of electronic structure. In the crystal structure, a short C-H
O interaction (HO = 2.34 Å) may help to establish the packing.
Equimolar quantities of Mo(CO)6, triphenylphosphine and 1,10-phenanthroline were refluxed in toluene under an N2 atmosphere for seven hours. After cooling, air-stable black slabs and blocks of (I) were recovered by vacuum filtration and rinsing with light petroleum ether in 79% yield based on Mo(CO)6. The crystals of (I) smear to a deep orange colour on a glass slide.
The hydrogen atoms were geometrically placed (C—H = 0.93 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).
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).
![[Figure 1]](./lh2494fig1thm.gif)
| Fig. 1. View of the molecular structure of (I) showing 50% displacement ellipsoids (H atoms omitted for clarity). |
| [Mo(CO)3(C18H15P)(C12H8N2)] | Z = 2 |
| Mr = 622.44 | F000 = 632 |
| Triclinic, P1 | Dx = 1.484 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 8.5179 (4) Å | Cell parameters from 6139 reflections |
| b = 9.6376 (4) Å | θ = 2.3–30.0º |
| c = 18.4119 (7) Å | µ = 0.57 mm−1 |
| α = 77.780 (1)º | T = 293 (2) K |
| β = 87.979 (1)º | Slab, black |
| γ = 70.723 (1)º | 0.35 × 0.26 × 0.11 mm |
| V = 1393.42 (10) Å3 |
| Bruker SMART 1000 CCD diffractometer | 7912 independent reflections |
| Radiation source: fine-focus sealed tube | 6552 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.015 |
| T = 293(2) K | θmax = 30.0º |
| ω scans | θmin = 2.3º |
| Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −11→11 |
| Tmin = 0.835, Tmax = 0.946 | k = −10→13 |
| 12111 measured reflections | l = −25→25 |
| 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)] = 0.029 | H-atom parameters constrained |
| wR(F2) = 0.068 | w = 1/[σ2(Fo2) + (0.036P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 0.95 | (Δ/σ)max = 0.001 |
| 7912 reflections | Δρmax = 0.63 e Å−3 |
| 361 parameters | Δρmin = −0.30 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| [Mo(CO)3(C18H15P)(C12H8N2)] | γ = 70.723 (1)º |
| Mr = 622.44 | V = 1393.42 (10) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 8.5179 (4) Å | Mo Kα |
| b = 9.6376 (4) Å | µ = 0.57 mm−1 |
| c = 18.4119 (7) Å | T = 293 (2) K |
| α = 77.780 (1)º | 0.35 × 0.26 × 0.11 mm |
| β = 87.979 (1)º |
| Bruker SMART 1000 CCD diffractometer | 7912 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 1999) | 6552 reflections with I > 2σ(I) |
| Tmin = 0.835, Tmax = 0.946 | Rint = 0.015 |
| 12111 measured reflections |
| R[F2 > 2σ(F2)] = 0.029 | 361 parameters |
| wR(F2) = 0.068 | H-atom parameters constrained |
| S = 0.95 | Δρmax = 0.63 e Å−3 |
| 7912 reflections | Δρmin = −0.30 e Å−3 |
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 > 2sigma(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 | 0.182959 (18) | −0.028421 (15) | 0.334120 (8) | 0.02732 (5) | |
| C1 | 0.1241 (2) | −0.11580 (19) | 0.43305 (10) | 0.0338 (4) | |
| C2 | 0.3428 (3) | −0.2261 (2) | 0.33681 (12) | 0.0483 (5) | |
| C3 | 0.0106 (3) | −0.0987 (2) | 0.30575 (10) | 0.0417 (4) | |
| O1 | 0.0855 (2) | −0.17694 (17) | 0.48803 (8) | 0.0563 (4) | |
| O2 | 0.4411 (2) | −0.34549 (18) | 0.34323 (14) | 0.0988 (7) | |
| O3 | −0.0968 (2) | −0.1451 (2) | 0.29626 (10) | 0.0769 (6) | |
| P1 | 0.25368 (6) | 0.07815 (5) | 0.20004 (2) | 0.03263 (10) | |
| C4 | −0.1324 (2) | 0.2719 (2) | 0.32076 (11) | 0.0409 (4) | |
| H4 | −0.1858 | 0.2202 | 0.2989 | 0.049* | |
| C5 | −0.2236 (3) | 0.4158 (2) | 0.33039 (13) | 0.0560 (6) | |
| H5 | −0.3350 | 0.4586 | 0.3146 | 0.067* | |
| C6 | −0.1495 (3) | 0.4932 (2) | 0.36277 (13) | 0.0565 (6) | |
| H6 | −0.2102 | 0.5888 | 0.3699 | 0.068* | |
| C7 | 0.0191 (3) | 0.4286 (2) | 0.38543 (11) | 0.0465 (5) | |
| C8 | 0.1042 (2) | 0.28319 (18) | 0.37319 (9) | 0.0341 (4) | |
| C9 | 0.2773 (2) | 0.2132 (2) | 0.39245 (9) | 0.0356 (4) | |
| C10 | 0.3628 (3) | 0.2892 (2) | 0.42524 (11) | 0.0483 (5) | |
| C11 | 0.5331 (3) | 0.2177 (3) | 0.44151 (12) | 0.0617 (7) | |
| H11 | 0.5935 | 0.2640 | 0.4632 | 0.074* | |
| C12 | 0.6104 (3) | 0.0801 (3) | 0.42563 (12) | 0.0586 (6) | |
| H12 | 0.7240 | 0.0324 | 0.4358 | 0.070* | |
| C13 | 0.5168 (2) | 0.0108 (2) | 0.39374 (11) | 0.0458 (5) | |
| H13 | 0.5709 | −0.0837 | 0.3836 | 0.055* | |
| C14 | 0.1082 (4) | 0.5014 (3) | 0.41967 (13) | 0.0616 (6) | |
| H14 | 0.0528 | 0.5967 | 0.4285 | 0.074* | |
| C15 | 0.2699 (4) | 0.4352 (3) | 0.43927 (13) | 0.0639 (7) | |
| H15 | 0.3237 | 0.4847 | 0.4625 | 0.077* | |
| C16 | 0.4248 (2) | −0.0531 (2) | 0.15991 (10) | 0.0363 (4) | |
| C17 | 0.5718 (2) | −0.1331 (2) | 0.20295 (11) | 0.0457 (5) | |
| H17 | 0.5813 | −0.1162 | 0.2503 | 0.055* | |
| C18 | 0.7025 (3) | −0.2362 (3) | 0.17655 (12) | 0.0535 (5) | |
| H18 | 0.8000 | −0.2863 | 0.2055 | 0.064* | |
| C19 | 0.6887 (3) | −0.2653 (3) | 0.10715 (13) | 0.0569 (6) | |
| H19 | 0.7755 | −0.3369 | 0.0898 | 0.068* | |
| C20 | 0.5452 (3) | −0.1874 (3) | 0.06374 (12) | 0.0569 (6) | |
| H20 | 0.5363 | −0.2054 | 0.0167 | 0.068* | |
| C21 | 0.4150 (3) | −0.0829 (2) | 0.08978 (11) | 0.0462 (5) | |
| H21 | 0.3190 | −0.0314 | 0.0599 | 0.055* | |
| C22 | 0.0873 (2) | 0.1417 (2) | 0.12703 (10) | 0.0371 (4) | |
| C23 | −0.0135 (3) | 0.0546 (2) | 0.12557 (11) | 0.0500 (5) | |
| H23 | 0.0013 | −0.0320 | 0.1622 | 0.060* | |
| C24 | −0.1362 (3) | 0.0959 (3) | 0.06987 (12) | 0.0617 (6) | |
| H24 | −0.2015 | 0.0356 | 0.0689 | 0.074* | |
| C25 | −0.1617 (3) | 0.2246 (3) | 0.01642 (13) | 0.0614 (6) | |
| H25 | −0.2463 | 0.2534 | −0.0199 | 0.074* | |
| C26 | −0.0620 (3) | 0.3109 (3) | 0.01664 (13) | 0.0671 (7) | |
| H26 | −0.0776 | 0.3974 | −0.0201 | 0.081* | |
| C27 | 0.0625 (3) | 0.2694 (2) | 0.07173 (12) | 0.0552 (6) | |
| H27 | 0.1299 | 0.3283 | 0.0713 | 0.066* | |
| C28 | 0.3183 (3) | 0.2461 (2) | 0.19056 (10) | 0.0397 (4) | |
| C29 | 0.2019 (3) | 0.3773 (2) | 0.20503 (11) | 0.0495 (5) | |
| H29 | 0.0940 | 0.3794 | 0.2163 | 0.059* | |
| C30 | 0.2460 (4) | 0.5050 (3) | 0.20269 (13) | 0.0658 (7) | |
| H30 | 0.1678 | 0.5915 | 0.2129 | 0.079* | |
| C31 | 0.4042 (4) | 0.5037 (3) | 0.18538 (15) | 0.0754 (8) | |
| H31 | 0.4334 | 0.5891 | 0.1838 | 0.091* | |
| C32 | 0.5193 (4) | 0.3760 (3) | 0.17038 (17) | 0.0797 (8) | |
| H32 | 0.6264 | 0.3754 | 0.1583 | 0.096* | |
| C33 | 0.4770 (3) | 0.2459 (3) | 0.17305 (14) | 0.0604 (6) | |
| H33 | 0.5561 | 0.1597 | 0.1630 | 0.072* | |
| N1 | 0.35406 (18) | 0.07416 (16) | 0.37739 (8) | 0.0339 (3) | |
| N2 | 0.02783 (17) | 0.20492 (15) | 0.34142 (8) | 0.0314 (3) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Mo1 | 0.02579 (7) | 0.02575 (7) | 0.02999 (7) | −0.00736 (5) | 0.00105 (5) | −0.00686 (5) |
| C1 | 0.0333 (9) | 0.0311 (9) | 0.0374 (9) | −0.0099 (7) | −0.0007 (7) | −0.0092 (7) |
| C2 | 0.0411 (11) | 0.0354 (10) | 0.0634 (13) | −0.0091 (8) | 0.0159 (9) | −0.0079 (9) |
| C3 | 0.0471 (11) | 0.0447 (11) | 0.0368 (9) | −0.0210 (9) | −0.0025 (8) | −0.0061 (8) |
| O1 | 0.0755 (11) | 0.0585 (9) | 0.0408 (8) | −0.0333 (8) | 0.0109 (7) | −0.0066 (7) |
| O2 | 0.0744 (13) | 0.0388 (10) | 0.155 (2) | 0.0073 (8) | 0.0483 (13) | −0.0085 (11) |
| O3 | 0.0799 (13) | 0.1001 (14) | 0.0739 (12) | −0.0637 (12) | −0.0134 (10) | −0.0101 (10) |
| P1 | 0.0331 (2) | 0.0361 (2) | 0.0309 (2) | −0.01468 (18) | 0.00072 (17) | −0.00656 (18) |
| C4 | 0.0322 (9) | 0.0352 (9) | 0.0498 (11) | −0.0053 (7) | 0.0011 (8) | −0.0066 (8) |
| C5 | 0.0441 (12) | 0.0420 (12) | 0.0666 (14) | 0.0031 (9) | 0.0037 (10) | −0.0074 (10) |
| C6 | 0.0643 (15) | 0.0306 (10) | 0.0620 (14) | −0.0002 (9) | 0.0122 (11) | −0.0099 (9) |
| C7 | 0.0686 (14) | 0.0304 (9) | 0.0411 (10) | −0.0174 (9) | 0.0122 (10) | −0.0089 (8) |
| C8 | 0.0445 (10) | 0.0279 (8) | 0.0313 (8) | −0.0144 (7) | 0.0065 (7) | −0.0061 (6) |
| C9 | 0.0437 (10) | 0.0385 (9) | 0.0299 (8) | −0.0218 (8) | 0.0019 (7) | −0.0057 (7) |
| C10 | 0.0642 (14) | 0.0552 (12) | 0.0393 (10) | −0.0386 (11) | 0.0007 (9) | −0.0088 (9) |
| C11 | 0.0700 (17) | 0.0840 (18) | 0.0513 (13) | −0.0525 (15) | −0.0044 (11) | −0.0127 (12) |
| C12 | 0.0388 (12) | 0.0898 (18) | 0.0516 (13) | −0.0317 (12) | −0.0075 (10) | −0.0062 (12) |
| C13 | 0.0334 (10) | 0.0623 (13) | 0.0408 (10) | −0.0166 (9) | −0.0018 (8) | −0.0073 (9) |
| C14 | 0.098 (2) | 0.0388 (12) | 0.0598 (14) | −0.0322 (12) | 0.0120 (13) | −0.0201 (10) |
| C15 | 0.104 (2) | 0.0557 (14) | 0.0555 (14) | −0.0526 (15) | 0.0049 (14) | −0.0204 (11) |
| C16 | 0.0338 (9) | 0.0425 (10) | 0.0366 (9) | −0.0184 (8) | 0.0059 (7) | −0.0086 (7) |
| C17 | 0.0380 (11) | 0.0622 (13) | 0.0377 (10) | −0.0164 (9) | 0.0031 (8) | −0.0127 (9) |
| C18 | 0.0363 (11) | 0.0648 (14) | 0.0537 (13) | −0.0115 (9) | 0.0047 (9) | −0.0097 (10) |
| C19 | 0.0478 (13) | 0.0612 (14) | 0.0623 (14) | −0.0143 (10) | 0.0175 (11) | −0.0229 (11) |
| C20 | 0.0595 (15) | 0.0702 (15) | 0.0460 (12) | −0.0197 (12) | 0.0117 (10) | −0.0274 (11) |
| C21 | 0.0482 (12) | 0.0553 (12) | 0.0371 (10) | −0.0177 (10) | 0.0018 (8) | −0.0131 (9) |
| C22 | 0.0352 (10) | 0.0430 (10) | 0.0331 (9) | −0.0142 (8) | −0.0003 (7) | −0.0059 (7) |
| C23 | 0.0584 (14) | 0.0593 (13) | 0.0389 (10) | −0.0318 (11) | −0.0049 (9) | −0.0031 (9) |
| C24 | 0.0593 (15) | 0.0878 (18) | 0.0500 (13) | −0.0416 (14) | −0.0090 (11) | −0.0102 (12) |
| C25 | 0.0494 (14) | 0.0791 (17) | 0.0519 (13) | −0.0184 (12) | −0.0175 (10) | −0.0069 (12) |
| C26 | 0.0755 (18) | 0.0570 (14) | 0.0594 (14) | −0.0207 (12) | −0.0278 (13) | 0.0106 (11) |
| C27 | 0.0574 (14) | 0.0531 (13) | 0.0543 (13) | −0.0255 (10) | −0.0145 (11) | 0.0049 (10) |
| C28 | 0.0496 (11) | 0.0428 (10) | 0.0330 (9) | −0.0250 (9) | 0.0003 (8) | −0.0056 (7) |
| C29 | 0.0644 (14) | 0.0451 (11) | 0.0436 (11) | −0.0267 (10) | 0.0081 (10) | −0.0066 (9) |
| C30 | 0.101 (2) | 0.0432 (12) | 0.0599 (14) | −0.0341 (13) | 0.0065 (13) | −0.0087 (10) |
| C31 | 0.103 (2) | 0.0654 (17) | 0.0790 (18) | −0.0579 (17) | 0.0007 (16) | −0.0122 (14) |
| C32 | 0.0749 (19) | 0.088 (2) | 0.099 (2) | −0.0591 (17) | 0.0076 (16) | −0.0172 (17) |
| C33 | 0.0570 (15) | 0.0611 (14) | 0.0736 (16) | −0.0326 (12) | 0.0038 (12) | −0.0159 (12) |
| N1 | 0.0314 (8) | 0.0402 (8) | 0.0312 (7) | −0.0145 (6) | 0.0001 (6) | −0.0053 (6) |
| N2 | 0.0310 (7) | 0.0266 (7) | 0.0340 (7) | −0.0074 (5) | 0.0034 (6) | −0.0049 (5) |
| Mo1—C2 | 1.933 (2) | C15—H15 | 0.9300 |
| Mo1—C3 | 1.9360 (18) | C16—C21 | 1.392 (2) |
| Mo1—C1 | 1.9604 (18) | C16—C17 | 1.401 (3) |
| Mo1—N2 | 2.2304 (14) | C17—C18 | 1.378 (3) |
| Mo1—N1 | 2.2589 (14) | C17—H17 | 0.9300 |
| Mo1—P1 | 2.5965 (5) | C18—C19 | 1.382 (3) |
| C1—O1 | 1.154 (2) | C18—H18 | 0.9300 |
| C2—O2 | 1.163 (2) | C19—C20 | 1.380 (3) |
| C3—O3 | 1.175 (2) | C19—H19 | 0.9300 |
| P1—C16 | 1.8368 (19) | C20—C21 | 1.380 (3) |
| P1—C22 | 1.8449 (18) | C20—H20 | 0.9300 |
| P1—C28 | 1.8483 (17) | C21—H21 | 0.9300 |
| C4—N2 | 1.332 (2) | C22—C27 | 1.382 (3) |
| C4—C5 | 1.393 (3) | C22—C23 | 1.389 (2) |
| C4—H4 | 0.9300 | C23—C24 | 1.390 (3) |
| C5—C6 | 1.355 (3) | C23—H23 | 0.9300 |
| C5—H5 | 0.9300 | C24—C25 | 1.369 (3) |
| C6—C7 | 1.402 (3) | C24—H24 | 0.9300 |
| C6—H6 | 0.9300 | C25—C26 | 1.372 (3) |
| C7—C8 | 1.411 (3) | C25—H25 | 0.9300 |
| C7—C14 | 1.428 (3) | C26—C27 | 1.392 (3) |
| C8—N2 | 1.369 (2) | C26—H26 | 0.9300 |
| C8—C9 | 1.426 (3) | C27—H27 | 0.9300 |
| C9—N1 | 1.366 (2) | C28—C33 | 1.379 (3) |
| C9—C10 | 1.415 (2) | C28—C29 | 1.395 (3) |
| C10—C11 | 1.397 (3) | C29—C30 | 1.393 (3) |
| C10—C15 | 1.441 (3) | C29—H29 | 0.9300 |
| C11—C12 | 1.360 (3) | C30—C31 | 1.370 (4) |
| C11—H11 | 0.9300 | C30—H30 | 0.9300 |
| C12—C13 | 1.407 (3) | C31—C32 | 1.372 (4) |
| C12—H12 | 0.9300 | C31—H31 | 0.9300 |
| C13—N1 | 1.333 (2) | C32—C33 | 1.405 (3) |
| C13—H13 | 0.9300 | C32—H32 | 0.9300 |
| C14—C15 | 1.339 (3) | C33—H33 | 0.9300 |
| C14—H14 | 0.9300 | ||
| C2—Mo1—C3 | 89.07 (9) | C21—C16—C17 | 117.52 (18) |
| C2—Mo1—C1 | 85.59 (8) | C21—C16—P1 | 123.70 (15) |
| C3—Mo1—C1 | 80.56 (7) | C17—C16—P1 | 118.73 (14) |
| C2—Mo1—N2 | 171.18 (7) | C18—C17—C16 | 121.27 (19) |
| C3—Mo1—N2 | 99.32 (7) | C18—C17—H17 | 119.4 |
| C1—Mo1—N2 | 93.09 (6) | C16—C17—H17 | 119.4 |
| C2—Mo1—N1 | 97.92 (7) | C17—C18—C19 | 120.1 (2) |
| C3—Mo1—N1 | 171.27 (7) | C17—C18—H18 | 120.0 |
| C1—Mo1—N1 | 94.70 (6) | C19—C18—H18 | 120.0 |
| N2—Mo1—N1 | 73.48 (5) | C20—C19—C18 | 119.6 (2) |
| C2—Mo1—P1 | 93.28 (6) | C20—C19—H19 | 120.2 |
| C3—Mo1—P1 | 96.47 (6) | C18—C19—H19 | 120.2 |
| C1—Mo1—P1 | 176.82 (5) | C21—C20—C19 | 120.4 (2) |
| N2—Mo1—P1 | 88.48 (4) | C21—C20—H20 | 119.8 |
| N1—Mo1—P1 | 88.40 (4) | C19—C20—H20 | 119.8 |
| O1—C1—Mo1 | 173.32 (15) | C20—C21—C16 | 121.15 (19) |
| O2—C2—Mo1 | 175.6 (2) | C20—C21—H21 | 119.4 |
| O3—C3—Mo1 | 173.06 (17) | C16—C21—H21 | 119.4 |
| C16—P1—C22 | 102.43 (8) | C27—C22—C23 | 118.30 (17) |
| C16—P1—C28 | 103.58 (9) | C27—C22—P1 | 122.83 (14) |
| C22—P1—C28 | 101.84 (8) | C23—C22—P1 | 118.82 (14) |
| C16—P1—Mo1 | 114.85 (6) | C22—C23—C24 | 120.53 (19) |
| C22—P1—Mo1 | 117.58 (6) | C22—C23—H23 | 119.7 |
| C28—P1—Mo1 | 114.60 (6) | C24—C23—H23 | 119.7 |
| N2—C4—C5 | 123.04 (18) | C25—C24—C23 | 120.5 (2) |
| N2—C4—H4 | 118.5 | C25—C24—H24 | 119.8 |
| C5—C4—H4 | 118.5 | C23—C24—H24 | 119.8 |
| C6—C5—C4 | 119.8 (2) | C24—C25—C26 | 119.7 (2) |
| C6—C5—H5 | 120.1 | C24—C25—H25 | 120.2 |
| C4—C5—H5 | 120.1 | C26—C25—H25 | 120.2 |
| C5—C6—C7 | 119.67 (19) | C25—C26—C27 | 120.2 (2) |
| C5—C6—H6 | 120.2 | C25—C26—H26 | 119.9 |
| C7—C6—H6 | 120.2 | C27—C26—H26 | 119.9 |
| C6—C7—C8 | 117.46 (18) | C22—C27—C26 | 120.8 (2) |
| C6—C7—C14 | 123.8 (2) | C22—C27—H27 | 119.6 |
| C8—C7—C14 | 118.7 (2) | C26—C27—H27 | 119.6 |
| N2—C8—C7 | 122.48 (18) | C33—C28—C29 | 118.79 (18) |
| N2—C8—C9 | 117.20 (15) | C33—C28—P1 | 123.17 (16) |
| C7—C8—C9 | 120.30 (16) | C29—C28—P1 | 117.98 (15) |
| N1—C9—C10 | 122.71 (18) | C30—C29—C28 | 120.6 (2) |
| N1—C9—C8 | 117.67 (14) | C30—C29—H29 | 119.7 |
| C10—C9—C8 | 119.62 (18) | C28—C29—H29 | 119.7 |
| C11—C10—C9 | 117.5 (2) | C31—C30—C29 | 120.2 (3) |
| C11—C10—C15 | 124.1 (2) | C31—C30—H30 | 119.9 |
| C9—C10—C15 | 118.3 (2) | C29—C30—H30 | 119.9 |
| C12—C11—C10 | 119.91 (19) | C30—C31—C32 | 119.8 (2) |
| C12—C11—H11 | 120.0 | C30—C31—H31 | 120.1 |
| C10—C11—H11 | 120.0 | C32—C31—H31 | 120.1 |
| C11—C12—C13 | 119.3 (2) | C31—C32—C33 | 120.7 (3) |
| C11—C12—H12 | 120.3 | C31—C32—H32 | 119.7 |
| C13—C12—H12 | 120.3 | C33—C32—H32 | 119.7 |
| N1—C13—C12 | 123.0 (2) | C28—C33—C32 | 120.0 (2) |
| N1—C13—H13 | 118.5 | C28—C33—H33 | 120.0 |
| C12—C13—H13 | 118.5 | C32—C33—H33 | 120.0 |
| C15—C14—C7 | 121.3 (2) | C13—N1—C9 | 117.47 (16) |
| C15—C14—H14 | 119.4 | C13—N1—Mo1 | 127.39 (13) |
| C7—C14—H14 | 119.4 | C9—N1—Mo1 | 115.00 (11) |
| C14—C15—C10 | 121.7 (2) | C4—N2—C8 | 117.53 (15) |
| C14—C15—H15 | 119.2 | C4—N2—Mo1 | 126.27 (12) |
| C10—C15—H15 | 119.2 | C8—N2—Mo1 | 116.14 (11) |
| C2—Mo1—P1—C16 | −3.87 (9) | C16—P1—C22—C23 | 84.52 (18) |
| C3—Mo1—P1—C16 | −93.31 (9) | C28—P1—C22—C23 | −168.51 (17) |
| N2—Mo1—P1—C16 | 167.49 (7) | Mo1—P1—C22—C23 | −42.39 (19) |
| N1—Mo1—P1—C16 | 93.97 (7) | C27—C22—C23—C24 | −0.2 (3) |
| C2—Mo1—P1—C22 | 116.76 (10) | P1—C22—C23—C24 | −177.66 (18) |
| C3—Mo1—P1—C22 | 27.33 (9) | C22—C23—C24—C25 | −1.3 (4) |
| N2—Mo1—P1—C22 | −71.88 (8) | C23—C24—C25—C26 | 2.0 (4) |
| N1—Mo1—P1—C22 | −145.40 (8) | C24—C25—C26—C27 | −1.2 (4) |
| C2—Mo1—P1—C28 | −123.64 (10) | C23—C22—C27—C26 | 1.0 (4) |
| C3—Mo1—P1—C28 | 146.92 (9) | P1—C22—C27—C26 | 178.3 (2) |
| N2—Mo1—P1—C28 | 47.71 (8) | C25—C26—C27—C22 | −0.3 (4) |
| N1—Mo1—P1—C28 | −25.80 (8) | C16—P1—C28—C33 | −13.0 (2) |
| N2—C4—C5—C6 | −0.7 (3) | C22—P1—C28—C33 | −119.11 (18) |
| C4—C5—C6—C7 | 0.8 (3) | Mo1—P1—C28—C33 | 112.84 (17) |
| C5—C6—C7—C8 | −0.1 (3) | C16—P1—C28—C29 | 169.78 (15) |
| C5—C6—C7—C14 | 179.7 (2) | C22—P1—C28—C29 | 63.70 (16) |
| C6—C7—C8—N2 | −0.8 (3) | Mo1—P1—C28—C29 | −64.35 (16) |
| C14—C7—C8—N2 | 179.33 (17) | C33—C28—C29—C30 | −0.8 (3) |
| C6—C7—C8—C9 | 177.72 (17) | P1—C28—C29—C30 | 176.55 (17) |
| C14—C7—C8—C9 | −2.1 (3) | C28—C29—C30—C31 | 0.7 (3) |
| N2—C8—C9—N1 | 0.4 (2) | C29—C30—C31—C32 | −0.1 (4) |
| C7—C8—C9—N1 | −178.20 (15) | C30—C31—C32—C33 | −0.4 (4) |
| N2—C8—C9—C10 | 179.80 (15) | C29—C28—C33—C32 | 0.3 (3) |
| C7—C8—C9—C10 | 1.2 (2) | P1—C28—C33—C32 | −176.86 (19) |
| N1—C9—C10—C11 | 0.8 (3) | C31—C32—C33—C28 | 0.3 (4) |
| C8—C9—C10—C11 | −178.51 (17) | C12—C13—N1—C9 | 0.3 (3) |
| N1—C9—C10—C15 | −179.60 (17) | C12—C13—N1—Mo1 | −175.18 (14) |
| C8—C9—C10—C15 | 1.1 (3) | C10—C9—N1—C13 | −1.0 (2) |
| C9—C10—C11—C12 | 0.1 (3) | C8—C9—N1—C13 | 178.33 (15) |
| C15—C10—C11—C12 | −179.4 (2) | C10—C9—N1—Mo1 | 175.01 (13) |
| C10—C11—C12—C13 | −0.8 (3) | C8—C9—N1—Mo1 | −5.63 (19) |
| C11—C12—C13—N1 | 0.6 (3) | C2—Mo1—N1—C13 | 3.59 (16) |
| C6—C7—C14—C15 | −179.0 (2) | C1—Mo1—N1—C13 | 89.77 (15) |
| C8—C7—C14—C15 | 0.8 (3) | N2—Mo1—N1—C13 | −178.39 (16) |
| C7—C14—C15—C10 | 1.5 (4) | P1—Mo1—N1—C13 | −89.50 (14) |
| C11—C10—C15—C14 | 177.1 (2) | C2—Mo1—N1—C9 | −171.98 (12) |
| C9—C10—C15—C14 | −2.4 (3) | C1—Mo1—N1—C9 | −85.79 (12) |
| C22—P1—C16—C21 | 1.63 (18) | N2—Mo1—N1—C9 | 6.04 (11) |
| C28—P1—C16—C21 | −104.00 (16) | P1—Mo1—N1—C9 | 94.93 (11) |
| Mo1—P1—C16—C21 | 130.28 (15) | C5—C4—N2—C8 | −0.3 (3) |
| C22—P1—C16—C17 | −175.63 (14) | C5—C4—N2—Mo1 | 176.72 (15) |
| C28—P1—C16—C17 | 78.74 (16) | C7—C8—N2—C4 | 1.0 (2) |
| Mo1—P1—C16—C17 | −46.98 (16) | C9—C8—N2—C4 | −177.56 (15) |
| C21—C16—C17—C18 | 0.7 (3) | C7—C8—N2—Mo1 | −176.28 (13) |
| P1—C16—C17—C18 | 178.11 (16) | C9—C8—N2—Mo1 | 5.13 (18) |
| C16—C17—C18—C19 | −1.6 (3) | C3—Mo1—N2—C4 | −8.00 (15) |
| C17—C18—C19—C20 | 1.8 (4) | C1—Mo1—N2—C4 | −88.93 (15) |
| C18—C19—C20—C21 | −1.1 (4) | N1—Mo1—N2—C4 | 177.08 (15) |
| C19—C20—C21—C16 | 0.2 (3) | P1—Mo1—N2—C4 | 88.30 (14) |
| C17—C16—C21—C20 | 0.1 (3) | C3—Mo1—N2—C8 | 169.03 (12) |
| P1—C16—C21—C20 | −177.23 (17) | C1—Mo1—N2—C8 | 88.10 (12) |
| C16—P1—C22—C27 | −92.80 (19) | N1—Mo1—N2—C8 | −5.88 (11) |
| C28—P1—C22—C27 | 14.2 (2) | P1—Mo1—N2—C8 | −94.66 (11) |
| Mo1—P1—C22—C27 | 140.29 (17) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C5—H5···O2i | 0.93 | 2.34 | 3.058 (3) | 134 |
| Symmetry codes: (i) x−1, y+1, z. |
| Mo1—C2 | 1.933 (2) | Mo1—N2 | 2.2304 (14) |
| Mo1—C3 | 1.9360 (18) | Mo1—N1 | 2.2589 (14) |
| Mo1—C1 | 1.9604 (18) | Mo1—P1 | 2.5965 (5) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C5—H5···O2i | 0.93 | 2.34 | 3.058 (3) | 134 |
| Symmetry codes: (i) x−1, y+1, z. |
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1995). International Tables for Crystallography, Vol. C, section 9.5, pp. 685–706. Dordrecht: Kluwer.
Bruker (1999). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cotton, F. A. & Wilkinson, G. (1966). Adv. Inorg. Chem., 2nd ed., pp. 781–782. New York: John Wiley.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565–?.
Howie, R. A. & McQuillan, G. P. (1986). J. Chem. Soc. Dalton Trans. pp. 759–764.
Muir, K. J., McQuillan, G. P. & Harrison, W. T. A. (2007). Acta Cryst. E63, m0000–?. [LH2495]
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.
The title compound, (I), Mo(CO)3(C18H15P)(C12H8N2), is an example of a trisubstituted group-6 metal hexacarbonyl (Howie & McQuillan, 1986). The related tricarbonyl-triphenylphosphine-2,2-bipyridyl-molybdenum(0) is described in the next 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 C16—C21/C22—C27 = 83.94 (11)°, C16—C21/C28—C33 = 71.77 (12)°, and C22—C27/C28—C33 = 67.95 (12)°. The N—Mo—N bite angle for the 1,10-phenanthroline (phen) molecule is 73.48 (5)°.
There is a slight distinction between the shorter Mo1—C2 and Mo1—C3 bond lengths trans to N atoms and and the longer Mo1—C1 bond, which is trans to the P atom. The traditional explanation (Cotton & Wilkinson, 1966) for this phenomenon is that triphenylphosphine is a π-acceptor ligand and completes for metal d electrons with the carbonyl group trans to itself, hence the Mo—C bond has less double-bond character than a Mo—C bond trans to an atom with no π-acceptor properties such as N, and is therefore longer. The C1—Mo1—P1 bond angle is also closer to linear than the C—Mo—N angles.
In the crystal of (I), a rather short C—H···O interaction arising from a phen C—H grouping (Table 2) may help to establish the packing.