(2,2′-Biquinoline)tetra­carbonyl­molybdenum(0)

Muir, K.J.; McQuillan, G.P.; Harrison, W.T.A.

doi:10.1107/S1600536807042547

(2,2′-Biquinoline)tetracarbonylmolybdenum(0)

K. J. Muir, G. P. McQuillan and W. T. A. Harrison

In the title compound, [Mo(C₁₈H₁₂N₂)(CO)₄], the differences in the Mo—C and C—O bond lengths may be interpreted in terms of a classical back-bonding model of electronic structure. In the crystal structure, an acute C—H

O interaction may help to establish the packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042547/bt2494sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042547/bt2494Isup2.hkl Contains datablock I

CCDC reference: 663546

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Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.031
wR factor = 0.079
Data-to-parameter ratio = 19.8

checkCIF/PLATON results

No syntax errors found



Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            very
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Mo1    -   C1      ..       8.52 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Mo1    -   C2      ..       7.33 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Mo1    -   C3      ..       6.13 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Mo1    -   C4      ..       8.03 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 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

Comment top

Although the substitution reactions of Mo(CO)₆ with amine bases have been intensively studied for many decades (Cotton & Wilkinson, 1966), the crystal structures of many of the resulting compounds remain to be studied. The structure of the simple compound Mo(CO)₄(C₁₀H₈N₂), (I), (Braga et al., 2007) has just been reported (C₁₀H₈N₂ = 2,2-bipyridine or bipy).

In the title compound, (II), Mo(CO)₄(C₁₈H₁₂N₂), 2,2'-biquinoline (biquin) has replaced bipy. A distorted cis-MoN₂C₄ octahedron results for the metal (Fig. 1, Table 1). The N—Mo—N bite angle for the biquin molecule is 72.31 (6)°. The dihedral angle between the N1/C5/C10—C13 and N2/C14—C17/C22 ring systems of 16.57 (11)° in (II) indicates a significant degree of twisting about the linking C13—C14 bond. The quinoline fused rings are slightly distorted from planarity: the C5—C10 and N1/C5/C10—C13 rings make a dihedral angle of 2.15 (11)°; C17—C22 and N2/C14—C17/C22 are twisted by 3.46 (12)°. Mo1 is close to coplanar with N1/C5/C10—C15 [displacement = -0.030 (1) Å] but substantially displaced, by 0.715 (1) Å, from N2/C14—C17/C22. Otherwise, all the biquin bond lengths and angles may be regarded as normal (Allen et al., 1995). The C2—Mo1—C4 bond angle of 169.31 (9)° indicates that these two carbonyl groups are bent away from the biquin molecule, perhaps for steric reasons.

The four Mo—C bond lengths in (II) fall into two groups of two. The shorter Mo1—C1 and Mo1—C3 bonds are trans to the diquin N atoms and the longer Mo1—C2 and Mo1—C4 bonds are trans to each other. The traditional explanation for this phenomenon assesses the π-acceptor propeties of the ligand trans to the carbon atom in question. If the trans atom has little or no π acceptor properties, then there is a greater tendency for the C atom to accept back bonded metal d electrons, and the Mo—C bond assumes a higher bond order and is shortened. Because the back bonded electrons are accommodated in the antibonding π* orbital of CO, the C—O bond length is expected to be lengthened as the Mo—C bond length decreases. This effect seems to be just visible in the present study, with the mean of C1—O1 and C3—O3 some 0.024 Å longer than the mean of C2—O2 and C4—O4.

In the crystal of (II), an acute C—H···O interaction (Table 2) may help to establish the packing. There are also a number of π-π stacking contacts with centroid-centroid separations in the range 3.6623 (13)–3.8227 (13) Å.

Related literature top

For a related structure, see: Braga et al., (2007). For background, see: Cotton & Wilkinson (1966). For reference structural data, see: Allen et al. (1995).

Experimental top

Equimolar quantities of Mo(CO)₆ and and 2,2'-biquinoline were refluxed in toluene under an N₂ atmosphere for six hours. After cooling, air-stable, dark orange, blocks of (II) were recovered by vacuum filtration and rinsing with light petroleum ether in 78% yield based on Mo(CO)₆.

Structure description top

For a related structure, see: Braga et al., (2007). For background, see: Cotton & Wilkinson (1966). For reference structural data, see: Allen et al. (1995).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; 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.

Figures top

Fig. 1. View of the molecular structure of the title compound showing 50% displacement ellipsoids (arbitrary spheres for the H atoms).

(2,2'-Biquinoline)tetracarbonylmolybdenum(0) top

Crystal data top

[Mo(C₁₈H₁₂N₂)(CO)₄]	Z = 2
M_r = 464.28	F(000) = 464
Triclinic, P1	D_x = 1.690 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7365 (4) Å	Cell parameters from 4201 reflections
b = 9.8294 (5) Å	θ = 2.6–29.8°
c = 12.8060 (6) Å	µ = 0.75 mm⁻¹
α = 93.512 (1)°	T = 296 K
β = 94.215 (1)°	Block, very dark orange
γ = 109.394 (1)°	0.42 × 0.18 × 0.12 mm
V = 912.29 (8) Å³

Data collection top

Bruker SMART1000 CCD diffractometer	5200 independent reflections
Radiation source: fine-focus sealed tube	4267 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 30.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −10→10
T_min = 0.743, T_max = 0.917	k = −13→12
8669 measured reflections	l = −17→15

Refinement top

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0418P)²] where P = (F_o² + 2F_c²)/3
5200 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

[Mo(C₁₈H₁₂N₂)(CO)₄]	γ = 109.394 (1)°
M_r = 464.28	V = 912.29 (8) Å³
Triclinic, P1	Z = 2
a = 7.7365 (4) Å	Mo Kα radiation
b = 9.8294 (5) Å	µ = 0.75 mm⁻¹
c = 12.8060 (6) Å	T = 296 K
α = 93.512 (1)°	0.42 × 0.18 × 0.12 mm
β = 94.215 (1)°

Data collection top

Bruker SMART1000 CCD diffractometer	5200 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	4267 reflections with I > 2σ(I)
T_min = 0.743, T_max = 0.917	R_int = 0.021
8669 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 0.99	Δρ_max = 0.59 e Å⁻³
5200 reflections	Δρ_min = −0.66 e Å⁻³
262 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Mo1	0.51011 (3)	0.182250 (18)	0.252976 (16)	0.03327 (7)
C1	0.4418 (3)	0.0088 (2)	0.1555 (2)	0.0449 (6)
C2	0.7505 (3)	0.2330 (3)	0.1855 (2)	0.0429 (5)
C3	0.6115 (4)	0.0645 (3)	0.3394 (2)	0.0480 (6)
C4	0.2617 (4)	0.0919 (3)	0.3117 (2)	0.0497 (6)
O1	0.4053 (3)	−0.0975 (2)	0.10119 (19)	0.0718 (6)
O2	0.8801 (3)	0.2432 (3)	0.14597 (19)	0.0728 (6)
O3	0.6716 (4)	−0.0104 (2)	0.3855 (2)	0.0820 (7)
O4	0.1260 (3)	0.0274 (3)	0.3410 (2)	0.0884 (8)
N1	0.4173 (2)	0.34601 (18)	0.16198 (14)	0.0305 (4)
N2	0.6003 (2)	0.39737 (18)	0.35795 (14)	0.0315 (4)
C5	0.3033 (3)	0.3170 (2)	0.06860 (17)	0.0318 (4)
C6	0.2348 (3)	0.1767 (2)	0.0164 (2)	0.0446 (6)
H6	0.2667	0.1025	0.0449	0.054*
C7	0.1222 (4)	0.1478 (3)	−0.0754 (2)	0.0514 (6)
H7	0.0809	0.0546	−0.1092	0.062*
C8	0.0679 (3)	0.2555 (3)	−0.1195 (2)	0.0487 (6)
H8	−0.0117	0.2335	−0.1810	0.058*
C9	0.1322 (3)	0.3924 (3)	−0.0720 (2)	0.0434 (5)
H9	0.0964	0.4643	−0.1015	0.052*
C10	0.2526 (3)	0.4278 (2)	0.02170 (18)	0.0339 (4)
C11	0.3256 (3)	0.5690 (2)	0.07031 (19)	0.0387 (5)
H11	0.2952	0.6435	0.0412	0.046*
C12	0.4409 (3)	0.5972 (2)	0.15997 (18)	0.0373 (5)
H12	0.4921	0.6913	0.1916	0.045*
C13	0.4835 (3)	0.4821 (2)	0.20574 (17)	0.0310 (4)
C14	0.5987 (3)	0.5123 (2)	0.30702 (17)	0.0324 (4)
C15	0.7002 (3)	0.6559 (2)	0.34873 (19)	0.0413 (5)
H15	0.6994	0.7330	0.3103	0.050*
C16	0.7981 (3)	0.6816 (2)	0.4437 (2)	0.0436 (5)
H16	0.8690	0.7758	0.4694	0.052*
C17	0.7923 (3)	0.5647 (2)	0.50393 (19)	0.0381 (5)
C18	0.8853 (3)	0.5847 (3)	0.6060 (2)	0.0470 (6)
H18	0.9556	0.6774	0.6352	0.056*
C19	0.8721 (4)	0.4689 (3)	0.6615 (2)	0.0536 (7)
H19	0.9360	0.4825	0.7278	0.064*
C20	0.7634 (4)	0.3295 (3)	0.6195 (2)	0.0502 (6)
H20	0.7525	0.2515	0.6593	0.060*
C21	0.6725 (3)	0.3061 (3)	0.5205 (2)	0.0431 (5)
H21	0.6002	0.2127	0.4940	0.052*
C22	0.6881 (3)	0.4231 (2)	0.45865 (17)	0.0340 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mo1	0.03857 (11)	0.02369 (9)	0.03904 (12)	0.01230 (7)	0.00274 (7)	0.00546 (7)
O1	0.0909 (16)	0.0349 (10)	0.0889 (17)	0.0275 (10)	−0.0093 (13)	−0.0141 (10)
O2	0.0544 (12)	0.0794 (15)	0.0858 (17)	0.0205 (11)	0.0272 (12)	0.0045 (12)
O3	0.114 (2)	0.0671 (14)	0.0856 (17)	0.0568 (14)	−0.0014 (14)	0.0281 (12)
O4	0.0646 (14)	0.0749 (16)	0.110 (2)	−0.0026 (12)	0.0359 (14)	0.0072 (14)
N1	0.0339 (9)	0.0258 (8)	0.0329 (10)	0.0116 (7)	0.0029 (7)	0.0040 (7)
N2	0.0342 (9)	0.0300 (8)	0.0321 (10)	0.0129 (7)	0.0029 (7)	0.0044 (7)
C1	0.0468 (13)	0.0303 (11)	0.0589 (16)	0.0156 (10)	−0.0004 (11)	0.0060 (10)
C2	0.0457 (13)	0.0359 (12)	0.0467 (14)	0.0141 (10)	0.0010 (11)	0.0034 (10)
C3	0.0590 (15)	0.0380 (12)	0.0519 (16)	0.0225 (11)	0.0034 (12)	0.0086 (11)
C4	0.0525 (15)	0.0379 (13)	0.0564 (17)	0.0124 (11)	0.0068 (12)	0.0013 (11)
C5	0.0333 (10)	0.0303 (10)	0.0329 (11)	0.0114 (8)	0.0052 (8)	0.0062 (8)
C6	0.0533 (14)	0.0295 (11)	0.0479 (14)	0.0122 (10)	−0.0062 (11)	0.0028 (10)
C7	0.0572 (15)	0.0369 (12)	0.0520 (16)	0.0086 (11)	−0.0083 (12)	−0.0002 (11)
C8	0.0447 (13)	0.0507 (14)	0.0439 (14)	0.0094 (11)	−0.0076 (11)	0.0064 (11)
C9	0.0433 (12)	0.0454 (13)	0.0438 (14)	0.0180 (10)	−0.0010 (10)	0.0108 (10)
C10	0.0343 (10)	0.0342 (10)	0.0361 (12)	0.0142 (8)	0.0046 (9)	0.0091 (9)
C11	0.0471 (13)	0.0326 (11)	0.0425 (13)	0.0201 (9)	0.0049 (10)	0.0106 (9)
C12	0.0488 (13)	0.0270 (10)	0.0393 (12)	0.0169 (9)	0.0035 (10)	0.0053 (8)
C13	0.0358 (10)	0.0258 (9)	0.0341 (11)	0.0138 (8)	0.0047 (8)	0.0023 (8)
C14	0.0379 (11)	0.0279 (9)	0.0333 (11)	0.0134 (8)	0.0048 (9)	0.0032 (8)
C15	0.0544 (14)	0.0278 (10)	0.0422 (13)	0.0158 (10)	0.0019 (11)	0.0016 (9)
C16	0.0487 (13)	0.0323 (11)	0.0458 (14)	0.0112 (10)	−0.0007 (11)	−0.0045 (10)
C17	0.0368 (11)	0.0427 (12)	0.0364 (12)	0.0165 (9)	0.0029 (9)	−0.0013 (9)
C18	0.0447 (13)	0.0547 (15)	0.0401 (14)	0.0179 (11)	−0.0020 (11)	−0.0048 (11)
C19	0.0498 (15)	0.0758 (19)	0.0369 (14)	0.0251 (14)	−0.0031 (11)	0.0058 (13)
C20	0.0535 (15)	0.0597 (16)	0.0415 (14)	0.0227 (13)	0.0037 (12)	0.0157 (12)
C21	0.0457 (13)	0.0445 (13)	0.0408 (14)	0.0161 (10)	0.0054 (10)	0.0111 (10)
C22	0.0337 (10)	0.0381 (11)	0.0332 (12)	0.0155 (9)	0.0047 (9)	0.0045 (9)

Geometric parameters (Å, º) top

Mo1—C1	1.946 (3)	C9—H9	0.9300
Mo1—C3	1.953 (3)	C10—C11	1.399 (3)
Mo1—C2	2.031 (3)	C11—C12	1.355 (3)
Mo1—C4	2.051 (3)	C11—H11	0.9300
Mo1—N2	2.3020 (18)	C12—C13	1.425 (3)
Mo1—N1	2.3107 (17)	C12—H12	0.9300
C1—O1	1.158 (3)	C13—C14	1.474 (3)
C2—O2	1.134 (3)	C14—C15	1.416 (3)
C3—O3	1.160 (3)	C15—C16	1.347 (3)
C4—O4	1.136 (3)	C15—H15	0.9300
N1—C13	1.333 (3)	C16—C17	1.413 (3)
N1—C5	1.388 (3)	C16—H16	0.9300
N2—C14	1.342 (3)	C17—C18	1.415 (3)
N2—C22	1.381 (3)	C17—C22	1.418 (3)
C5—C6	1.406 (3)	C18—C19	1.357 (4)
C5—C10	1.425 (3)	C18—H18	0.9300
C6—C7	1.367 (4)	C19—C20	1.397 (4)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.397 (4)	C20—C21	1.371 (4)
C7—H7	0.9300	C20—H20	0.9300
C8—C9	1.357 (4)	C21—C22	1.414 (3)
C8—H8	0.9300	C21—H21	0.9300
C9—C10	1.413 (3)

C1—Mo1—C3	81.52 (11)	C11—C10—C9	122.2 (2)
C1—Mo1—C2	83.18 (10)	C11—C10—C5	118.3 (2)
C3—Mo1—C2	85.46 (11)	C9—C10—C5	119.5 (2)
C1—Mo1—C4	86.98 (10)	C12—C11—C10	119.83 (19)
C3—Mo1—C4	88.99 (11)	C12—C11—H11	120.1
C2—Mo1—C4	169.31 (9)	C10—C11—H11	120.1
C1—Mo1—N2	175.64 (9)	C11—C12—C13	119.9 (2)
C3—Mo1—N2	101.26 (9)	C11—C12—H12	120.1
C2—Mo1—N2	93.66 (8)	C13—C12—H12	120.1
C4—Mo1—N2	96.38 (8)	N1—C13—C12	122.3 (2)
C1—Mo1—N1	104.72 (8)	N1—C13—C14	118.33 (17)
C3—Mo1—N1	172.97 (9)	C12—C13—C14	119.36 (18)
C2—Mo1—N1	92.03 (8)	N2—C14—C15	122.0 (2)
C4—Mo1—N1	94.50 (9)	N2—C14—C13	116.71 (18)
N2—Mo1—N1	72.31 (6)	C15—C14—C13	121.33 (19)
C13—N1—C5	118.22 (17)	C16—C15—C14	120.4 (2)
C13—N1—Mo1	114.78 (14)	C16—C15—H15	119.8
C5—N1—Mo1	127.00 (13)	C14—C15—H15	119.8
C14—N2—C22	117.79 (18)	C15—C16—C17	119.6 (2)
C14—N2—Mo1	114.41 (14)	C15—C16—H16	120.2
C22—N2—Mo1	126.38 (13)	C17—C16—H16	120.2
O1—C1—Mo1	176.5 (2)	C16—C17—C18	122.5 (2)
O2—C2—Mo1	171.4 (2)	C16—C17—C22	117.6 (2)
O3—C3—Mo1	176.1 (3)	C18—C17—C22	119.9 (2)
O4—C4—Mo1	172.3 (2)	C19—C18—C17	120.2 (2)
N1—C5—C6	120.94 (19)	C19—C18—H18	119.9
N1—C5—C10	121.43 (19)	C17—C18—H18	119.9
C6—C5—C10	117.6 (2)	C18—C19—C20	120.5 (2)
C7—C6—C5	121.1 (2)	C18—C19—H19	119.8
C7—C6—H6	119.5	C20—C19—H19	119.8
C5—C6—H6	119.5	C21—C20—C19	120.9 (2)
C6—C7—C8	121.2 (2)	C21—C20—H20	119.6
C6—C7—H7	119.4	C19—C20—H20	119.6
C8—C7—H7	119.4	C20—C21—C22	120.4 (2)
C9—C8—C7	119.4 (2)	C20—C21—H21	119.8
C9—C8—H8	120.3	C22—C21—H21	119.8
C7—C8—H8	120.3	N2—C22—C21	119.8 (2)
C8—C9—C10	121.1 (2)	N2—C22—C17	122.11 (19)
C8—C9—H9	119.4	C21—C22—C17	118.1 (2)
C10—C9—H9	119.4

C1—Mo1—N1—C13	−167.03 (16)	C5—N1—C13—C12	0.1 (3)
C2—Mo1—N1—C13	−83.56 (16)	Mo1—N1—C13—C12	179.76 (16)
C4—Mo1—N1—C13	104.91 (16)	C5—N1—C13—C14	177.65 (18)
N2—Mo1—N1—C13	9.64 (14)	Mo1—N1—C13—C14	−2.7 (2)
C1—Mo1—N1—C5	12.61 (19)	C11—C12—C13—N1	1.7 (3)
C2—Mo1—N1—C5	96.09 (17)	C11—C12—C13—C14	−175.8 (2)
C4—Mo1—N1—C5	−75.44 (18)	C22—N2—C14—C15	7.0 (3)
N2—Mo1—N1—C5	−170.72 (18)	Mo1—N2—C14—C15	−160.21 (17)
C3—Mo1—N2—C14	160.90 (16)	C22—N2—C14—C13	−172.04 (18)
C2—Mo1—N2—C14	74.80 (16)	Mo1—N2—C14—C13	20.7 (2)
C4—Mo1—N2—C14	−108.86 (16)	N1—C13—C14—N2	−12.3 (3)
N1—Mo1—N2—C14	−16.16 (14)	C12—C13—C14—N2	165.3 (2)
C3—Mo1—N2—C22	−5.07 (19)	N1—C13—C14—C15	168.6 (2)
C2—Mo1—N2—C22	−91.17 (18)	C12—C13—C14—C15	−13.8 (3)
C4—Mo1—N2—C22	85.17 (18)	N2—C14—C15—C16	−2.1 (4)
N1—Mo1—N2—C22	177.87 (18)	C13—C14—C15—C16	176.9 (2)
C13—N1—C5—C6	177.5 (2)	C14—C15—C16—C17	−2.9 (4)
Mo1—N1—C5—C6	−2.1 (3)	C15—C16—C17—C18	−177.2 (2)
C13—N1—C5—C10	−2.0 (3)	C15—C16—C17—C22	2.7 (3)
Mo1—N1—C5—C10	178.40 (14)	C16—C17—C18—C19	178.6 (2)
N1—C5—C6—C7	179.9 (2)	C22—C17—C18—C19	−1.2 (4)
C10—C5—C6—C7	−0.6 (4)	C17—C18—C19—C20	−1.6 (4)
C5—C6—C7—C8	−1.4 (4)	C18—C19—C20—C21	2.0 (4)
C6—C7—C8—C9	1.9 (4)	C19—C20—C21—C22	0.4 (4)
C7—C8—C9—C10	−0.3 (4)	C14—N2—C22—C21	171.6 (2)
C8—C9—C10—C11	177.8 (2)	Mo1—N2—C22—C21	−22.9 (3)
C8—C9—C10—C5	−1.8 (4)	C14—N2—C22—C17	−7.2 (3)
N1—C5—C10—C11	2.1 (3)	Mo1—N2—C22—C17	158.32 (16)
C6—C5—C10—C11	−177.4 (2)	C20—C21—C22—N2	178.1 (2)
N1—C5—C10—C9	−178.3 (2)	C20—C21—C22—C17	−3.1 (3)
C6—C5—C10—C9	2.2 (3)	C16—C17—C22—N2	2.5 (3)
C9—C10—C11—C12	−179.8 (2)	C18—C17—C22—N2	−177.7 (2)
C5—C10—C11—C12	−0.2 (3)	C16—C17—C22—C21	−176.4 (2)
C10—C11—C12—C13	−1.6 (3)	C18—C17—C22—C21	3.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1ⁱ	0.93	2.45	3.122 (3)	129

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Mo(C₁₈H₁₂N₂)(CO)₄]
M_r	464.28
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.7365 (4), 9.8294 (5), 12.8060 (6)
α, β, γ (°)	93.512 (1), 94.215 (1), 109.394 (1)
V (Å³)	912.29 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.75
Crystal size (mm)	0.42 × 0.18 × 0.12

Data collection
Diffractometer	Bruker SMART1000 CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.743, 0.917
No. of measured, independent and observed [I > 2σ(I)] reflections	8669, 5200, 4267
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.079, 0.99
No. of reflections	5200
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.66

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Selected bond lengths (Å) top

Mo1—C1	1.946 (3)	Mo1—N1	2.3107 (17)
Mo1—C3	1.953 (3)	C1—O1	1.158 (3)
Mo1—C2	2.031 (3)	C2—O2	1.134 (3)
Mo1—C4	2.051 (3)	C3—O3	1.160 (3)
Mo1—N2	2.3020 (18)	C4—O4	1.136 (3)