Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705461X/lh2540sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680705461X/lh2540Isup2.hkl |
CCDC reference: 672600
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.021
- wR factor = 0.061
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mo1 - C1 .. 7.48 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mo1 - C2 .. 6.89 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mo1 - C3 .. 7.57 su PLAT352_ALERT_3_C Short N-H Bond (0.87A) N4 - H1 ... 0.75 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N4 - H1 ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For the previous structure, see: Howie & McQuillan (1986). For a related structure, see: Braga et al. (2007). For background, see: Chisholm et al. (1981); Muir et al. (2007). For reference structural data, see: Allen et al. (1987).
The title compound was prepared by the method of Howie & McQuillan (1986), to result in dark green facted chunks of (I).
The N-bound H atom was located in a difference map and its position was freely refined with Uiso(H) = 1.2Ueq(C). The C-bound 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).
Fig. 1. View of the molecular structure of (I) showing 50% displacement ellipsoids (arbitrary spheres for the H atoms). The C—H···N and N—H···C contacts are indicated by double-dashed lines. |
[Mo(C10H8N2)(C10H9N3)(CO)3] | F(000) = 1024 |
Mr = 507.36 | Dx = 1.557 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6454 reflections |
a = 10.6273 (4) Å | θ = 2.6–25.0° |
b = 12.9092 (5) Å | µ = 0.64 mm−1 |
c = 16.5581 (7) Å | T = 298 K |
β = 107.728 (1)° | Faceted chunk, dark green |
V = 2163.73 (15) Å3 | 0.28 × 0.17 × 0.15 mm |
Z = 4 |
Bruker SMART1000 CCD diffractometer | 3811 independent reflections |
Radiation source: fine-focus sealed tube | 3067 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −12→12 |
Tmin = 0.841, Tmax = 0.910 | k = −15→8 |
12826 measured reflections | l = −19→19 |
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)] = 0.021 | Hydrogen site location: difmap and geom |
wR(F2) = 0.061 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0355P)2] where P = (Fo2 + 2Fc2)/3 |
3811 reflections | (Δ/σ)max < 0.001 |
292 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
[Mo(C10H8N2)(C10H9N3)(CO)3] | V = 2163.73 (15) Å3 |
Mr = 507.36 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.6273 (4) Å | µ = 0.64 mm−1 |
b = 12.9092 (5) Å | T = 298 K |
c = 16.5581 (7) Å | 0.28 × 0.17 × 0.15 mm |
β = 107.728 (1)° |
Bruker SMART1000 CCD diffractometer | 3811 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | 3067 reflections with I > 2σ(I) |
Tmin = 0.841, Tmax = 0.910 | Rint = 0.023 |
12826 measured reflections |
R[F2 > 2σ(F2)] = 0.021 | 0 restraints |
wR(F2) = 0.061 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.26 e Å−3 |
3811 reflections | Δρmin = −0.30 e Å−3 |
292 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 | 0.293621 (15) | 0.246228 (12) | 0.062933 (10) | 0.03100 (7) | |
C1 | 0.4599 (2) | 0.20447 (19) | 0.14032 (14) | 0.0466 (5) | |
O1 | 0.56041 (18) | 0.17911 (17) | 0.18766 (11) | 0.0830 (7) | |
C2 | 0.3533 (2) | 0.38617 (17) | 0.09857 (14) | 0.0441 (5) | |
O2 | 0.39753 (18) | 0.46686 (13) | 0.12363 (13) | 0.0774 (6) | |
C3 | 0.2294 (2) | 0.23659 (16) | 0.16098 (15) | 0.0434 (5) | |
O3 | 0.1968 (2) | 0.22860 (15) | 0.22132 (12) | 0.0708 (5) | |
C4 | 0.4438 (2) | 0.29588 (18) | −0.07405 (13) | 0.0430 (5) | |
H4 | 0.4450 | 0.3628 | −0.0531 | 0.052* | |
C5 | 0.5102 (2) | 0.2769 (2) | −0.13158 (15) | 0.0514 (6) | |
H5 | 0.5549 | 0.3298 | −0.1494 | 0.062* | |
C6 | 0.5094 (2) | 0.1782 (2) | −0.16237 (15) | 0.0569 (6) | |
H6 | 0.5551 | 0.1630 | −0.2007 | 0.068* | |
C7 | 0.4403 (2) | 0.10208 (18) | −0.13597 (14) | 0.0490 (6) | |
H7 | 0.4374 | 0.0351 | −0.1571 | 0.059* | |
C8 | 0.37499 (19) | 0.12607 (15) | −0.07757 (12) | 0.0359 (4) | |
C9 | 0.29805 (19) | 0.04888 (15) | −0.04587 (12) | 0.0367 (4) | |
C10 | 0.2805 (2) | −0.05268 (17) | −0.07389 (16) | 0.0565 (6) | |
H10 | 0.3158 | −0.0751 | −0.1158 | 0.068* | |
C11 | 0.2103 (3) | −0.1206 (2) | −0.03941 (19) | 0.0695 (8) | |
H11 | 0.1989 | −0.1893 | −0.0572 | 0.083* | |
C12 | 0.1579 (3) | −0.08492 (19) | 0.02146 (18) | 0.0646 (7) | |
H12 | 0.1095 | −0.1288 | 0.0454 | 0.078* | |
C13 | 0.1779 (2) | 0.01607 (17) | 0.04632 (15) | 0.0492 (6) | |
H13 | 0.1417 | 0.0395 | 0.0875 | 0.059* | |
C14 | 0.0659 (2) | 0.25571 (15) | −0.11820 (13) | 0.0408 (5) | |
H14 | 0.1342 | 0.2228 | −0.1322 | 0.049* | |
C15 | −0.0520 (2) | 0.26647 (17) | −0.18039 (14) | 0.0472 (5) | |
H15 | −0.0637 | 0.2406 | −0.2346 | 0.057* | |
C16 | −0.1531 (2) | 0.31653 (19) | −0.16073 (14) | 0.0510 (6) | |
H16 | −0.2348 | 0.3243 | −0.2016 | 0.061* | |
C17 | −0.1328 (2) | 0.35484 (17) | −0.08060 (14) | 0.0445 (5) | |
H17 | −0.2000 | 0.3896 | −0.0667 | 0.053* | |
C18 | −0.01035 (19) | 0.34098 (14) | −0.02039 (12) | 0.0343 (4) | |
C19 | −0.0613 (2) | 0.41246 (15) | 0.10733 (14) | 0.0420 (5) | |
C20 | −0.0031 (3) | 0.45981 (18) | 0.18505 (15) | 0.0553 (6) | |
H20 | 0.0880 | 0.4679 | 0.2059 | 0.066* | |
C21 | −0.0838 (3) | 0.4944 (2) | 0.23039 (18) | 0.0704 (8) | |
H21 | −0.0478 | 0.5280 | 0.2820 | 0.084* | |
C22 | −0.2169 (3) | 0.4793 (2) | 0.1995 (2) | 0.0757 (9) | |
H22 | −0.2731 | 0.5029 | 0.2289 | 0.091* | |
C23 | −0.2650 (3) | 0.4286 (3) | 0.1243 (2) | 0.0771 (9) | |
H23 | −0.3556 | 0.4170 | 0.1039 | 0.093* | |
N1 | 0.37697 (16) | 0.22289 (13) | −0.04629 (10) | 0.0338 (4) | |
N2 | 0.24692 (16) | 0.08371 (12) | 0.01458 (10) | 0.0362 (4) | |
N3 | 0.09003 (15) | 0.28956 (13) | −0.03790 (10) | 0.0334 (4) | |
N4 | 0.02063 (17) | 0.38006 (14) | 0.06062 (12) | 0.0425 (4) | |
H1 | 0.092 (2) | 0.3747 (18) | 0.0863 (15) | 0.051* | |
N5 | −0.18931 (19) | 0.39405 (18) | 0.07744 (13) | 0.0613 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mo1 | 0.02958 (11) | 0.03322 (11) | 0.03088 (11) | 0.00259 (7) | 0.01021 (7) | −0.00083 (7) |
C1 | 0.0443 (13) | 0.0572 (14) | 0.0381 (12) | 0.0153 (11) | 0.0123 (10) | −0.0112 (11) |
O1 | 0.0575 (11) | 0.1274 (18) | 0.0493 (10) | 0.0485 (12) | −0.0058 (9) | −0.0205 (11) |
C2 | 0.0337 (12) | 0.0440 (13) | 0.0542 (13) | 0.0039 (10) | 0.0129 (10) | −0.0072 (11) |
O2 | 0.0640 (12) | 0.0469 (11) | 0.1135 (16) | −0.0102 (9) | 0.0157 (11) | −0.0252 (11) |
C3 | 0.0446 (13) | 0.0456 (13) | 0.0414 (12) | 0.0071 (10) | 0.0152 (10) | 0.0041 (10) |
O3 | 0.0838 (14) | 0.0897 (14) | 0.0520 (11) | 0.0104 (10) | 0.0404 (10) | 0.0140 (10) |
C4 | 0.0430 (12) | 0.0423 (12) | 0.0446 (12) | −0.0060 (10) | 0.0148 (10) | 0.0014 (10) |
C5 | 0.0495 (14) | 0.0606 (15) | 0.0492 (14) | −0.0088 (11) | 0.0224 (11) | 0.0077 (12) |
C6 | 0.0608 (16) | 0.0700 (17) | 0.0523 (15) | 0.0061 (13) | 0.0359 (13) | 0.0064 (13) |
C7 | 0.0567 (14) | 0.0491 (13) | 0.0484 (13) | 0.0056 (11) | 0.0267 (11) | −0.0032 (11) |
C8 | 0.0349 (11) | 0.0383 (11) | 0.0348 (11) | 0.0042 (9) | 0.0111 (9) | 0.0010 (9) |
C9 | 0.0379 (11) | 0.0334 (10) | 0.0400 (11) | 0.0035 (8) | 0.0133 (9) | 0.0010 (9) |
C10 | 0.0677 (16) | 0.0409 (13) | 0.0696 (16) | −0.0010 (12) | 0.0338 (14) | −0.0110 (12) |
C11 | 0.085 (2) | 0.0335 (13) | 0.096 (2) | −0.0095 (12) | 0.0367 (18) | −0.0079 (14) |
C12 | 0.0745 (18) | 0.0425 (14) | 0.0856 (19) | −0.0114 (12) | 0.0373 (16) | 0.0078 (14) |
C13 | 0.0529 (14) | 0.0426 (13) | 0.0602 (14) | −0.0023 (10) | 0.0289 (12) | 0.0056 (11) |
C14 | 0.0407 (12) | 0.0436 (12) | 0.0388 (12) | 0.0034 (9) | 0.0130 (9) | 0.0007 (10) |
C15 | 0.0467 (13) | 0.0551 (14) | 0.0360 (12) | −0.0026 (10) | 0.0068 (10) | −0.0013 (10) |
C16 | 0.0344 (12) | 0.0646 (16) | 0.0466 (13) | −0.0024 (11) | 0.0016 (10) | 0.0084 (12) |
C17 | 0.0331 (12) | 0.0490 (13) | 0.0512 (13) | 0.0056 (9) | 0.0123 (10) | 0.0047 (11) |
C18 | 0.0329 (11) | 0.0283 (10) | 0.0424 (12) | −0.0008 (8) | 0.0127 (9) | 0.0009 (9) |
C19 | 0.0472 (13) | 0.0297 (11) | 0.0547 (13) | 0.0061 (9) | 0.0237 (11) | 0.0007 (10) |
C20 | 0.0629 (16) | 0.0502 (14) | 0.0593 (15) | −0.0063 (12) | 0.0282 (13) | −0.0088 (12) |
C21 | 0.094 (2) | 0.0616 (17) | 0.0717 (18) | −0.0064 (15) | 0.0492 (17) | −0.0165 (14) |
C22 | 0.085 (2) | 0.0731 (19) | 0.090 (2) | 0.0147 (16) | 0.0577 (19) | −0.0087 (17) |
C23 | 0.0532 (16) | 0.097 (2) | 0.092 (2) | 0.0115 (15) | 0.0374 (16) | −0.0075 (19) |
N1 | 0.0320 (9) | 0.0344 (9) | 0.0361 (9) | −0.0006 (7) | 0.0123 (7) | −0.0003 (7) |
N2 | 0.0376 (9) | 0.0333 (9) | 0.0394 (9) | 0.0016 (7) | 0.0145 (8) | 0.0031 (7) |
N3 | 0.0317 (9) | 0.0330 (8) | 0.0363 (9) | −0.0003 (7) | 0.0116 (7) | 0.0011 (7) |
N4 | 0.0336 (10) | 0.0474 (11) | 0.0454 (11) | 0.0060 (9) | 0.0104 (8) | −0.0069 (9) |
N5 | 0.0445 (12) | 0.0743 (15) | 0.0701 (14) | 0.0044 (10) | 0.0251 (11) | −0.0134 (12) |
Mo1—C1 | 1.917 (2) | C12—H12 | 0.9300 |
Mo1—C2 | 1.946 (2) | C13—N2 | 1.346 (3) |
Mo1—C3 | 1.947 (2) | C13—H13 | 0.9300 |
Mo1—N2 | 2.2465 (16) | C14—N3 | 1.348 (3) |
Mo1—N1 | 2.2631 (16) | C14—C15 | 1.365 (3) |
Mo1—N3 | 2.3626 (16) | C14—H14 | 0.9300 |
C1—O1 | 1.163 (3) | C15—C16 | 1.375 (3) |
C2—O2 | 1.166 (3) | C15—H15 | 0.9300 |
C3—O3 | 1.158 (3) | C16—C17 | 1.370 (3) |
C4—N1 | 1.342 (3) | C16—H16 | 0.9300 |
C4—C5 | 1.369 (3) | C17—C18 | 1.389 (3) |
C4—H4 | 0.9300 | C17—H17 | 0.9300 |
C5—C6 | 1.371 (3) | C18—N3 | 1.360 (2) |
C5—H5 | 0.9300 | C18—N4 | 1.376 (3) |
C6—C7 | 1.376 (3) | C19—N5 | 1.320 (3) |
C6—H6 | 0.9300 | C19—C20 | 1.388 (3) |
C7—C8 | 1.386 (3) | C19—N4 | 1.393 (3) |
C7—H7 | 0.9300 | C20—C21 | 1.375 (3) |
C8—N1 | 1.351 (2) | C20—H20 | 0.9300 |
C8—C9 | 1.483 (3) | C21—C22 | 1.363 (4) |
C9—N2 | 1.353 (2) | C21—H21 | 0.9300 |
C9—C10 | 1.384 (3) | C22—C23 | 1.360 (4) |
C10—C11 | 1.383 (3) | C22—H22 | 0.9300 |
C10—H10 | 0.9300 | C23—N5 | 1.352 (3) |
C11—C12 | 1.372 (4) | C23—H23 | 0.9300 |
C11—H11 | 0.9300 | N4—H1 | 0.75 (2) |
C12—C13 | 1.364 (3) | ||
C1—Mo1—C2 | 84.81 (10) | N2—C13—H13 | 118.1 |
C1—Mo1—C3 | 84.86 (9) | C12—C13—H13 | 118.1 |
C2—Mo1—C3 | 88.34 (9) | N3—C14—C15 | 124.5 (2) |
C1—Mo1—N2 | 91.96 (8) | N3—C14—H14 | 117.8 |
C2—Mo1—N2 | 172.47 (7) | C15—C14—H14 | 117.8 |
C3—Mo1—N2 | 98.16 (7) | C14—C15—C16 | 118.2 (2) |
C1—Mo1—N1 | 89.51 (7) | C14—C15—H15 | 120.9 |
C2—Mo1—N1 | 101.27 (7) | C16—C15—H15 | 120.9 |
C3—Mo1—N1 | 168.40 (7) | C17—C16—C15 | 119.7 (2) |
N2—Mo1—N1 | 71.86 (6) | C17—C16—H16 | 120.2 |
C1—Mo1—N3 | 176.56 (7) | C15—C16—H16 | 120.2 |
C2—Mo1—N3 | 97.94 (7) | C16—C17—C18 | 119.1 (2) |
C3—Mo1—N3 | 97.25 (8) | C16—C17—H17 | 120.5 |
N2—Mo1—N3 | 85.06 (6) | C18—C17—H17 | 120.5 |
N1—Mo1—N3 | 87.93 (6) | N3—C18—N4 | 114.60 (17) |
O1—C1—Mo1 | 179.6 (2) | N3—C18—C17 | 122.26 (18) |
O2—C2—Mo1 | 175.0 (2) | N4—C18—C17 | 123.12 (18) |
O3—C3—Mo1 | 176.8 (2) | N5—C19—C20 | 123.0 (2) |
N1—C4—C5 | 123.4 (2) | N5—C19—N4 | 119.0 (2) |
N1—C4—H4 | 118.3 | C20—C19—N4 | 118.0 (2) |
C5—C4—H4 | 118.3 | C21—C20—C19 | 118.2 (2) |
C4—C5—C6 | 118.6 (2) | C21—C20—H20 | 120.9 |
C4—C5—H5 | 120.7 | C19—C20—H20 | 120.9 |
C6—C5—H5 | 120.7 | C22—C21—C20 | 119.8 (3) |
C5—C6—C7 | 119.3 (2) | C22—C21—H21 | 120.1 |
C5—C6—H6 | 120.4 | C20—C21—H21 | 120.1 |
C7—C6—H6 | 120.4 | C23—C22—C21 | 118.0 (2) |
C6—C7—C8 | 119.4 (2) | C23—C22—H22 | 121.0 |
C6—C7—H7 | 120.3 | C21—C22—H22 | 121.0 |
C8—C7—H7 | 120.3 | N5—C23—C22 | 124.1 (3) |
N1—C8—C7 | 121.44 (19) | N5—C23—H23 | 118.0 |
N1—C8—C9 | 115.60 (16) | C22—C23—H23 | 118.0 |
C7—C8—C9 | 122.96 (19) | C4—N1—C8 | 117.80 (17) |
N2—C9—C10 | 121.29 (19) | C4—N1—Mo1 | 123.83 (14) |
N2—C9—C8 | 115.31 (17) | C8—N1—Mo1 | 117.73 (12) |
C10—C9—C8 | 123.40 (18) | C13—N2—C9 | 117.56 (18) |
C11—C10—C9 | 119.8 (2) | C13—N2—Mo1 | 123.65 (14) |
C11—C10—H10 | 120.1 | C9—N2—Mo1 | 118.63 (13) |
C9—C10—H10 | 120.1 | C14—N3—C18 | 116.25 (17) |
C12—C11—C10 | 118.8 (2) | C14—N3—Mo1 | 118.60 (13) |
C12—C11—H11 | 120.6 | C18—N3—Mo1 | 125.01 (12) |
C10—C11—H11 | 120.6 | C18—N4—C19 | 130.30 (18) |
C13—C12—C11 | 118.8 (2) | C18—N4—H1 | 114.7 (18) |
C13—C12—H12 | 120.6 | C19—N4—H1 | 114.1 (18) |
C11—C12—H12 | 120.6 | C19—N5—C23 | 116.8 (2) |
N2—C13—C12 | 123.8 (2) | ||
C6—C7—C8—N1 | 0.4 (3) | N3—Mo1—N1—C8 | −93.96 (14) |
C6—C7—C8—C9 | 179.9 (2) | C12—C13—N2—C9 | 0.5 (3) |
N1—C8—C9—N2 | −4.2 (3) | C12—C13—N2—Mo1 | −174.87 (19) |
C7—C8—C9—N2 | 176.34 (19) | C10—C9—N2—C13 | −0.2 (3) |
N1—C8—C9—C10 | 177.0 (2) | C8—C9—N2—C13 | −179.04 (18) |
C7—C8—C9—C10 | −2.4 (3) | C10—C9—N2—Mo1 | 175.43 (16) |
N2—C9—C10—C11 | −0.5 (4) | C8—C9—N2—Mo1 | −3.4 (2) |
C8—C9—C10—C11 | 178.2 (2) | C1—Mo1—N2—C13 | 92.67 (18) |
C9—C10—C11—C12 | 0.9 (4) | C3—Mo1—N2—C13 | 7.58 (19) |
C10—C11—C12—C13 | −0.6 (4) | N1—Mo1—N2—C13 | −178.49 (18) |
C11—C12—C13—N2 | −0.1 (4) | N3—Mo1—N2—C13 | −89.06 (17) |
N3—C14—C15—C16 | 1.0 (3) | C1—Mo1—N2—C9 | −82.70 (15) |
C14—C15—C16—C17 | 0.7 (3) | C3—Mo1—N2—C9 | −167.79 (15) |
C15—C16—C17—C18 | −0.8 (3) | N1—Mo1—N2—C9 | 6.14 (14) |
C16—C17—C18—N3 | −0.7 (3) | N3—Mo1—N2—C9 | 95.57 (14) |
C16—C17—C18—N4 | 177.5 (2) | C15—C14—N3—C18 | −2.5 (3) |
N5—C19—C20—C21 | −3.9 (4) | C15—C14—N3—Mo1 | 173.32 (16) |
N4—C19—C20—C21 | 178.3 (2) | N4—C18—N3—C14 | −176.06 (17) |
C19—C20—C21—C22 | 1.6 (4) | C17—C18—N3—C14 | 2.3 (3) |
C20—C21—C22—C23 | 0.8 (4) | N4—C18—N3—Mo1 | 8.4 (2) |
C21—C22—C23—N5 | −1.4 (5) | C17—C18—N3—Mo1 | −173.20 (14) |
C5—C4—N1—C8 | −0.5 (3) | C2—Mo1—N3—C14 | 123.55 (15) |
C5—C4—N1—Mo1 | 170.18 (17) | C3—Mo1—N3—C14 | −147.12 (15) |
C7—C8—N1—C4 | 0.4 (3) | N2—Mo1—N3—C14 | −49.50 (14) |
C9—C8—N1—C4 | −179.05 (18) | N1—Mo1—N3—C14 | 22.46 (14) |
C7—C8—N1—Mo1 | −170.80 (16) | C2—Mo1—N3—C18 | −61.04 (16) |
C9—C8—N1—Mo1 | 9.7 (2) | C3—Mo1—N3—C18 | 28.29 (16) |
C1—Mo1—N1—C4 | −86.90 (18) | N2—Mo1—N3—C18 | 125.91 (15) |
C2—Mo1—N1—C4 | −2.29 (18) | N1—Mo1—N3—C18 | −162.13 (15) |
C3—Mo1—N1—C4 | −147.7 (4) | N3—C18—N4—C19 | −161.7 (2) |
N2—Mo1—N1—C4 | −179.13 (17) | C17—C18—N4—C19 | 19.9 (3) |
N3—Mo1—N1—C4 | 95.40 (17) | N5—C19—N4—C18 | 9.2 (3) |
C1—Mo1—N1—C8 | 83.75 (16) | C20—C19—N4—C18 | −172.9 (2) |
C2—Mo1—N1—C8 | 168.36 (14) | C20—C19—N5—C23 | 3.4 (4) |
C3—Mo1—N1—C8 | 22.9 (4) | N4—C19—N5—C23 | −178.9 (2) |
N2—Mo1—N1—C8 | −8.48 (13) | C22—C23—N5—C19 | −0.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H1···C3 | 0.75 (2) | 2.40 (2) | 2.978 (3) | 135 (2) |
C17—H17···N5 | 0.93 | 2.36 | 2.902 (3) | 117 |
C10—H10···O1i | 0.93 | 2.43 | 3.318 (3) | 160 |
C16—H16···O1ii | 0.93 | 2.38 | 3.305 (3) | 172 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x−1, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Mo(C10H8N2)(C10H9N3)(CO)3] |
Mr | 507.36 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 10.6273 (4), 12.9092 (5), 16.5581 (7) |
β (°) | 107.728 (1) |
V (Å3) | 2163.73 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.64 |
Crystal size (mm) | 0.28 × 0.17 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART1000 CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1999) |
Tmin, Tmax | 0.841, 0.910 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12826, 3811, 3067 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.021, 0.061, 1.06 |
No. of reflections | 3811 |
No. of parameters | 292 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.26, −0.30 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).
Mo1—C1 | 1.917 (2) | Mo1—N2 | 2.2465 (16) |
Mo1—C2 | 1.946 (2) | Mo1—N1 | 2.2631 (16) |
Mo1—C3 | 1.947 (2) | Mo1—N3 | 2.3626 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H1···C3 | 0.75 (2) | 2.40 (2) | 2.978 (3) | 135 (2) |
C17—H17···N5 | 0.93 | 2.36 | 2.902 (3) | 117 |
C10—H10···O1i | 0.93 | 2.43 | 3.318 (3) | 160 |
C16—H16···O1ii | 0.93 | 2.38 | 3.305 (3) | 172 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x−1, −y+1/2, z−1/2. |
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The synthesis and structure of the title compound, (I), Mo(CO)3(bipy)(dipyam) (bipy = 2,2-bipyridine, C10H8N2; dipyam = di-2-pyridylamine, C10H9N3) was reported by Howie & McQuillan (1986). We report here a corrected structure, in which an N atom and C—H group are exchanged (Fig. 1). The previous determination did not locate the H atoms, and swapped atoms C20 and N5 (using the present numbering scheme). The revised structure is supported by (i) a lower R-factor (compared to swapped N and C atoms); (ii) a significant difference peak near C20 corresponding to an H atom, but little or no evidence of such a feature near N5; (iii) the plausible formation of an intramolecular C17—H17···N5 interaction; (iv) the C19—N5 bond length of 1.320 (3) Å found here would be extremely short for an aromatic C—C bond, but is quite acceptable for an aromatic C—N bond.
Otherwise, the structure of (I) is similar to the previous determination with improved precision [e.g. σ values for the Mo—N bonds in (I) = 0.0016 Å compared to 0.006 Å in the previous study], and features a distorted mer-MoC3N3 octahedron for the metal atom (Table 1). Mo1—C1 is slightly shorter than the other two Mo—C distances, perhaps because the weak π* acceptor capabilities of the N atoms of the bipy and bonded dipyam rings are slightly different (Chisholm et al., 1981).
The N—Mo—N bite angle for the bipy molecule in (I) is 71.86 (6)°, which is typical (Braga et al., 2007). The dihedral angle between the N1/C4—C8 and N2/C9—C13 ring systems of 3.56 (16)° indicates a small degree of twisting about the linking C8—C9 bond. Even so, Mo1 is significantly displaced from both the N1/C4—C8 and N2/C9—C13 ring planes, by 0.329 (3) Å and 0.168 (3) Å, respectively. The dihedral angle between the N3/C14—C18 and N5/C19—C23 ring planes is 24.91 (9)°. Otherwise, all the organic bond lengths and angles in (I) may be regarded as normal (Allen et al., 1987).
The most unusual feature of (I) is a short intramolecular N—H···C distance of 2.40 (2) Å (Table 2). The van der Waals radius sum for H and C is 2.90 Å. This novel interaction – or incidental steric contact – will be discussed in more detail elsewhere (Muir et al., 2007).
In the crystal of (I), two relatively short C—H···O interactions (Table 2) may help to establish the packing. Any aromatic π-π stacking in (I) must be weak, with a minimum centroid-centroid separation of 3.94 Å.