Difluoridodioxido(1,10-phenanthroline)molybdenum(VI)

Wang, W.; Zhang, Y.; Jin, X.; Du, X.

doi:10.1107/S1600536809031626

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page m1094

doi:10.1107/S1600536809031626

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Difluoridodioxido(1,10-phenanthroline)molybdenum(VI)

Wenju Wang,^a ^* Youdi Zhang,^b Xiangjun Jin ^a and Xiguang Du ^b

^aDepartment of Chemistry, Baicheng Normal College, Baicheng, Jiln 137000, People's Republic of China, and ^bCollege of Chemistry, Northeast Normal University, Changchun, Jilin 130024, People's Republic of China
^*Correspondence e-mail: wangwj3309@126.com

(Received 28 July 2009; accepted 11 August 2009; online 19 August 2009)

The title compound, [MoF₂O₂(C₁₂H₈N₂)], has non-crystallographic mirror symmetry. The Mo^VI atom shows a distorted octahedral environment, with the phenanthroline N atoms and the two oxide groups forming the equatorial plane and the F atoms occupying the apical positions. Weak C—H⋯O and C—H⋯F hydrogen-bonding contacts and π–π interactions [centroid–centroid distance = 3.662 (1) Å] connect the complex molecules into a three-dimensional supramolecular framework.

Related literature

For the structure and mode of action of the co-factor of oxido-molybdoenzymes, see: Collison et al. (1996 ). For the catalyst precursors, see Villata et al. (2000 ). For the dichloridodioxo analogue of the title compound, see: Viossat & Rodier (1979 ). For other related structures with the chelating phenanthroline ligand, see: Butcher et al. (1979 ); Bingham et al. (2006 ); Zhou et al. (2000 ).

Experimental

Crystal data

[MoF₂O₂(C₁₂H₈N₂)]
M_r = 346.14
Monoclinic, P 2₁ /c
a = 7.5190 (9) Å
b = 17.818 (2) Å
c = 9.5331 (11) Å
β = 110.8560 (10)°
V = 1193.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.12 mm⁻¹
T = 295 K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.711, T_max = 0.799
6460 measured reflections
2394 independent reflections
2248 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.065
S = 1.04
2394 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Selected bond lengths (Å)

Mo1—O2	1.6874 (18)
Mo1—O1	1.6936 (17)
Mo1—F1	1.9017 (14)
Mo1—F2	1.9049 (13)
Mo1—N2	2.3257 (18)
Mo1—N1	2.3295 (18)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2C⋯F1ⁱ	0.93	2.45	3.202 (3)	138
C3—H3C⋯O1ⁱⁱ	0.93	2.55	3.376 (3)	148
C7—H7⋯F1ⁱⁱⁱ	0.93	2.44	3.191 (3)	137
C8—H8⋯O2^iv	0.93	2.59	3.222 (3)	126
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x-1, y, z-1; (iii) -x+1, -y+1, -z; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2001 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809031626/si2192sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809031626/si2192Isup2.hkl

checkCIF report

Comment top

The high oxidation state oxomolybdenum(VI) can be potentially used as molybdoenzyme, oxo transfer agents, and catalyst precusors [Collison, et al., (1996); Villata, et al., (2000)]. Though some MoO₂X₂ (X = Cl, Br) complexes have been reported [Butcher, et al. (1979)], these compounds are usually unstable in air. Thus, the air stable dioxomolybdenum(VI) complex remains an intriguing area for chemists [Bingham, et al. (2006)]. In this paper, we reported a new fluorin containing oxomolybdenum(VI) complex that is stable in air.

As shown in Fig. 1, the title complex exhibits non-crystallographic molecular mirror symmetry. The distorted octahedral environment around molybdenum consists of cis terminal oxygen atoms (O_t) and trans fluorin atoms and bidentate 1,10-phenanthroline ligand. One mirror plane can be seen bisecting the atoms F1-Mo1-F2 and extending through the midpoints of the central C—C bonds of the phenanthroline ligand, while another mirror can be imagined within the phenanthroline plane and the Mo and dioxo atoms. The average Mo—O_t bond distance of 1.691 Å (Table 1) is a typical molybdenum-oxygen terminal double bond and is similar to those observed in MoO₂X₂.2L complexes [Butcher, et al. (1979)]. The Mo—N bond distances (2.326 (2) Å and 2.330 (2) Å) are also similar to those values observed in analogue complexes [Bingham, et al. (2006); Viossat & Rodier, (1979)]. However, the Mo—F bond distances of 1.905 (1) Å and 1.902 (1) Å for the title compound are transparently shorter than the Mo—Cl or Mo—Br bonds determined in other MoO₂X₂ (X = Cl, Br) complexes [For MoO₂Cl₂ complex, see: Viossat & Rodier, (1979); for MoO₂X₂.2L complexes, see: Butcher, et al. (1979)]. This is the main reason that the title compound is stable in air. Furthermore, there also exist weak C—H···F and C—H···O hydrogen bonding interactions between neighboring molecules which plays an important role to consolidate the supramolecular structure of the title compund. The detailed hydrogen bond parameters are shown in Table 2. Molybdenum and 1,10-phenanthroline complexes were substantively reported [Zhou, et al. (2000); Viossat & Rodier, (1979); Butcher, et al. (1979)], but it was quite missing that some references described the distinctive nature or features of π–π interaction. Whereas for the title complex, the 1,10-phenanthroline phenyl ring induced π–π interaction is demonstrated to aid the three-dimensional structure together with the weak hydrogen bonding contacts (Fig. 2). The centroid to centroid distance is 3.6619 (14) Å. (Cg3···Cg3îii^, Cg3 is the centroid of the ring (N2 C9 C8 C7 C6 C10), symmetry code iii = 1 - x, 1 - y, -z). The perpendicular distance of the rings is 3.369 Å and the slippage between the rings is 1.435 Å.

Related literature top

For the structure and mode of action of the co-factor of oxo-molybdoenzymes, see: Collison et al. (1996). For the catalyst precursors, see Villata et al. (2000). For the dichlorodioxo analogue of the title compound, see: Viossat & Rodier (1979). For other related structures with the chelating phenanthroline ligand, see: Butcher et al. (1979); Bingham et al. (2006); Zhou et al. (2000).

Experimental top

A mixture of Molybdenum trioxide (0.2874 g, 2 mmol), HF (2 ml), 1,10-phenanthroline(0.2246 g, 1.1 mmol) and N,N-dimethylformamide (30 ml) was stirring for 7 h under 343 K. After cooling to room temperature, the mixture was adjusted to pH = 6.05 with 6 M H₂SO₄ solution. The filtration was allowed to stand over several days to give colorless block single crystals in 80% yield. Analysis calculated for C₁₂H₈F₂MoN₂O₂: C 41.64, H 2.33, N 8.09, F 10.98%; found: C 41.60, H 2.30, N 8.06, F 10.94%.

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The local coordination environment of the Mo(VI) atom in the title compound drawn with 30% probability. H atoms omitted for clarity.
	Fig. 2. The three-dimensional supramolecular network of the title compund produced by hydrogen-bonding and π–π stacking interactions.[Color codes: Mo, pink; O, red; F, yellow; N, blue; C, grey. Symmetry codes: (i) x - 1, -y + 1/2, z - 1/2; (ii) x - 1, y, z - 1; (iii) -x + 1, -y + 1, -z; (iv) -x + 1, y + 1/2, -z + 1/2.]

Difluoridodioxido(1,10-phenanthroline)molybdenum(VI) top

Crystal data top

[MoF₂O₂(C₁₂H₈N₂)]	F(000) = 680
M_r = 346.14	D_x = 1.926 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 7.5190 (9) Å	θ = 7.5–15°
b = 17.818 (2) Å	µ = 1.12 mm⁻¹
c = 9.5331 (11) Å	T = 295 K
β = 110.856 (1)°	Block, colorless
V = 1193.5 (2) Å³	0.30 × 0.30 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	2248 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 26.2°, θ_min = 2.6°
ω scans	h = −9→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −15→22
T_min = 0.711, T_max = 0.799	l = −11→11
6460 measured reflections	2 standard reflections every 150 reflections
2394 independent reflections	intensity decay: none

Refinement top

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)] = 0.022	H-atom parameters constrained
wR(F²) = 0.065	w = 1/[σ²(F_o²) + (0.04P)² + 0.45P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2394 reflections	Δρ_max = 0.46 e Å⁻³
173 parameters	Δρ_min = −0.59 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.0345 (14)
Primary atom site location: structure-invariant direct methods

Crystal data top

[MoF₂O₂(C₁₂H₈N₂)]	V = 1193.5 (2) Å³
M_r = 346.14	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5190 (9) Å	µ = 1.12 mm⁻¹
b = 17.818 (2) Å	T = 295 K
c = 9.5331 (11) Å	0.30 × 0.30 × 0.20 mm
β = 110.856 (1)°

Data collection top

Bruker APEXII diffractometer	2248 reflections with I > 2σ(I)
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	R_int = 0.023
T_min = 0.711, T_max = 0.799	2 standard reflections every 150 reflections
6460 measured reflections	intensity decay: none
2394 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.065	H-atom parameters constrained
S = 1.04	Δρ_max = 0.46 e Å⁻³
2394 reflections	Δρ_min = −0.59 e Å⁻³
173 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	0.46789 (2)	0.344747 (10)	0.354935 (18)	0.03131 (11)
F1	0.62030 (19)	0.32745 (9)	0.23609 (16)	0.0466 (3)
F2	0.25657 (19)	0.38491 (8)	0.39576 (15)	0.0441 (3)
O1	0.6429 (3)	0.38223 (12)	0.50412 (19)	0.0548 (5)
O2	0.4418 (3)	0.25454 (10)	0.3980 (2)	0.0531 (5)
N1	0.2347 (2)	0.32975 (10)	0.1180 (2)	0.0305 (4)
N2	0.4234 (2)	0.45752 (10)	0.22405 (18)	0.0299 (4)
C1	0.1412 (3)	0.26638 (13)	0.0684 (3)	0.0397 (5)
H1	0.1689	0.2247	0.1313	0.048*
C2	0.0030 (3)	0.25974 (15)	−0.0746 (3)	0.0477 (6)
H2C	−0.0610	0.2145	−0.1052	0.057*
C3	−0.0379 (3)	0.31953 (18)	−0.1689 (3)	0.0462 (6)
H3C	−0.1304	0.3155	−0.2643	0.055*
C4	0.0602 (3)	0.38758 (14)	−0.1221 (2)	0.0365 (5)
C5	0.1962 (3)	0.38964 (12)	0.0244 (2)	0.0282 (4)
C6	0.2597 (3)	0.52244 (13)	−0.0100 (2)	0.0343 (4)
C7	0.3596 (3)	0.58803 (13)	0.0530 (3)	0.0417 (5)
H7	0.3414	0.6317	−0.0037	0.050*
C8	0.4833 (4)	0.58742 (13)	0.1978 (3)	0.0442 (5)
H8	0.5477	0.6309	0.2414	0.053*
C9	0.5125 (3)	0.52088 (13)	0.2799 (3)	0.0376 (5)
H9	0.5982	0.5210	0.3783	0.045*
C10	0.2964 (3)	0.45787 (11)	0.0808 (2)	0.0281 (4)
C11	0.0272 (3)	0.45398 (16)	−0.2121 (2)	0.0456 (6)
H11	−0.0617	0.4529	−0.3093	0.055*
C12	0.1218 (3)	0.51780 (15)	−0.1590 (3)	0.0443 (6)
H12	0.0974	0.5600	−0.2204	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mo1	0.03177 (14)	0.03595 (15)	0.02202 (14)	0.00454 (6)	0.00442 (9)	0.00358 (6)
F1	0.0367 (7)	0.0648 (9)	0.0385 (7)	0.0141 (6)	0.0137 (6)	0.0061 (7)
F2	0.0462 (7)	0.0492 (8)	0.0420 (7)	0.0054 (6)	0.0220 (6)	−0.0004 (6)
O1	0.0492 (10)	0.0685 (13)	0.0312 (9)	−0.0001 (9)	−0.0045 (8)	−0.0006 (8)
O2	0.0691 (12)	0.0409 (10)	0.0500 (10)	0.0100 (8)	0.0223 (9)	0.0131 (8)
N1	0.0280 (8)	0.0330 (9)	0.0283 (9)	0.0003 (7)	0.0073 (7)	−0.0023 (7)
N2	0.0287 (8)	0.0329 (9)	0.0256 (8)	−0.0001 (7)	0.0067 (7)	−0.0006 (7)
C1	0.0349 (11)	0.0369 (12)	0.0453 (13)	−0.0036 (9)	0.0116 (10)	−0.0063 (10)
C2	0.0335 (11)	0.0517 (15)	0.0535 (15)	−0.0088 (10)	0.0102 (11)	−0.0207 (12)
C3	0.0266 (11)	0.0688 (17)	0.0355 (12)	0.0024 (10)	0.0016 (9)	−0.0172 (12)
C4	0.0240 (9)	0.0558 (14)	0.0265 (10)	0.0064 (9)	0.0052 (8)	−0.0044 (9)
C5	0.0230 (9)	0.0381 (11)	0.0223 (9)	0.0047 (7)	0.0067 (7)	−0.0017 (8)
C6	0.0332 (10)	0.0396 (11)	0.0349 (11)	0.0099 (9)	0.0181 (9)	0.0081 (9)
C7	0.0499 (13)	0.0352 (12)	0.0496 (14)	0.0079 (10)	0.0296 (12)	0.0091 (10)
C8	0.0536 (14)	0.0333 (12)	0.0537 (15)	−0.0079 (10)	0.0290 (12)	−0.0064 (10)
C9	0.0375 (11)	0.0396 (12)	0.0341 (11)	−0.0050 (9)	0.0109 (9)	−0.0066 (9)
C10	0.0252 (9)	0.0349 (10)	0.0247 (9)	0.0060 (7)	0.0097 (7)	0.0013 (8)
C11	0.0335 (11)	0.0714 (17)	0.0265 (11)	0.0142 (11)	0.0042 (9)	0.0071 (11)
C12	0.0404 (12)	0.0587 (15)	0.0346 (11)	0.0186 (11)	0.0142 (10)	0.0183 (11)

Geometric parameters (Å, º) top

Mo1—O2	1.6874 (18)	C3—H3C	0.9300
Mo1—O1	1.6936 (17)	C4—C5	1.407 (3)
Mo1—F1	1.9017 (14)	C4—C11	1.430 (4)
Mo1—F2	1.9049 (13)	C5—C10	1.431 (3)
Mo1—N2	2.3257 (18)	C6—C7	1.403 (3)
Mo1—N1	2.3295 (18)	C6—C10	1.407 (3)
N1—C1	1.325 (3)	C6—C12	1.432 (3)
N1—C5	1.355 (3)	C7—C8	1.362 (4)
N2—C9	1.324 (3)	C7—H7	0.9300
N2—C10	1.360 (2)	C8—C9	1.395 (3)
C1—C2	1.394 (3)	C8—H8	0.9300
C1—H1	0.9300	C9—H9	0.9300
C2—C3	1.357 (4)	C11—C12	1.341 (4)
C2—H2C	0.9300	C11—H11	0.9300
C3—C4	1.407 (4)	C12—H12	0.9300

O2—Mo1—O1	107.12 (10)	C4—C3—H3C	120.1
O2—Mo1—F1	97.89 (8)	C3—C4—C5	116.8 (2)
O1—Mo1—F1	96.38 (8)	C3—C4—C11	124.3 (2)
O2—Mo1—F2	97.50 (8)	C5—C4—C11	118.9 (2)
O1—Mo1—F2	97.80 (8)	N1—C5—C4	122.9 (2)
F1—Mo1—F2	154.96 (6)	N1—C5—C10	117.49 (17)
O2—Mo1—N2	161.15 (8)	C4—C5—C10	119.63 (19)
O1—Mo1—N2	91.73 (8)	C7—C6—C10	117.4 (2)
F1—Mo1—N2	79.77 (6)	C7—C6—C12	124.1 (2)
F2—Mo1—N2	79.28 (6)	C10—C6—C12	118.5 (2)
O2—Mo1—N1	90.79 (8)	C8—C7—C6	119.7 (2)
O1—Mo1—N1	162.00 (8)	C8—C7—H7	120.1
F1—Mo1—N1	78.99 (6)	C6—C7—H7	120.1
F2—Mo1—N1	81.17 (6)	C7—C8—C9	119.3 (2)
N2—Mo1—N1	70.38 (6)	C7—C8—H8	120.3
C1—N1—C5	118.29 (19)	C9—C8—H8	120.3
C1—N1—Mo1	124.37 (16)	N2—C9—C8	122.9 (2)
C5—N1—Mo1	117.32 (13)	N2—C9—H9	118.6
C9—N2—C10	118.29 (19)	C8—C9—H9	118.6
C9—N2—Mo1	124.43 (14)	N2—C10—C6	122.38 (19)
C10—N2—Mo1	117.28 (13)	N2—C10—C5	117.45 (17)
N1—C1—C2	122.5 (2)	C6—C10—C5	120.16 (18)
N1—C1—H1	118.7	C12—C11—C4	121.3 (2)
C2—C1—H1	118.7	C12—C11—H11	119.3
C3—C2—C1	119.7 (2)	C4—C11—H11	119.3
C3—C2—H2C	120.2	C11—C12—C6	121.5 (2)
C1—C2—H2C	120.2	C11—C12—H12	119.2
C2—C3—C4	119.8 (2)	C6—C12—H12	119.2
C2—C3—H3C	120.1

O2—Mo1—N1—C1	0.08 (18)	Mo1—N1—C5—C10	−2.4 (2)
O1—Mo1—N1—C1	174.5 (3)	C3—C4—C5—N1	0.4 (3)
F1—Mo1—N1—C1	97.96 (18)	C11—C4—C5—N1	179.07 (19)
F2—Mo1—N1—C1	−97.39 (17)	C3—C4—C5—C10	−177.92 (18)
N2—Mo1—N1—C1	−179.08 (18)	C11—C4—C5—C10	0.8 (3)
O2—Mo1—N1—C5	−178.35 (15)	C10—C6—C7—C8	−1.2 (3)
O1—Mo1—N1—C5	−3.9 (3)	C12—C6—C7—C8	177.7 (2)
F1—Mo1—N1—C5	−80.46 (14)	C6—C7—C8—C9	1.6 (3)
F2—Mo1—N1—C5	84.18 (14)	C10—N2—C9—C8	−0.8 (3)
N2—Mo1—N1—C5	2.49 (13)	Mo1—N2—C9—C8	179.51 (16)
O2—Mo1—N2—C9	174.7 (2)	C7—C8—C9—N2	−0.6 (3)
O1—Mo1—N2—C9	−4.66 (18)	C9—N2—C10—C6	1.3 (3)
F1—Mo1—N2—C9	−100.83 (17)	Mo1—N2—C10—C6	−179.05 (14)
F2—Mo1—N2—C9	92.95 (17)	C9—N2—C10—C5	−177.63 (18)
N1—Mo1—N2—C9	177.31 (18)	Mo1—N2—C10—C5	2.1 (2)
O2—Mo1—N2—C10	−5.0 (3)	C7—C6—C10—N2	−0.3 (3)
O1—Mo1—N2—C10	175.66 (15)	C12—C6—C10—N2	−179.26 (19)
F1—Mo1—N2—C10	79.49 (14)	C7—C6—C10—C5	178.60 (17)
F2—Mo1—N2—C10	−86.72 (14)	C12—C6—C10—C5	−0.4 (3)
N1—Mo1—N2—C10	−2.37 (13)	N1—C5—C10—N2	0.2 (3)
C5—N1—C1—C2	−1.4 (3)	C4—C5—C10—N2	178.62 (17)
Mo1—N1—C1—C2	−179.78 (17)	N1—C5—C10—C6	−178.69 (17)
N1—C1—C2—C3	0.9 (4)	C4—C5—C10—C6	−0.3 (3)
C1—C2—C3—C4	0.3 (4)	C3—C4—C11—C12	178.0 (2)
C2—C3—C4—C5	−0.9 (3)	C5—C4—C11—C12	−0.6 (3)
C2—C3—C4—C11	−179.5 (2)	C4—C11—C12—C6	−0.2 (3)
C1—N1—C5—C4	0.7 (3)	C7—C6—C12—C11	−178.3 (2)
Mo1—N1—C5—C4	179.25 (14)	C10—C6—C12—C11	0.6 (3)
C1—N1—C5—C10	179.07 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2C···F1ⁱ	0.93	2.45	3.202 (3)	138
C3—H3C···O1ⁱⁱ	0.93	2.55	3.376 (3)	148
C7—H7···F1ⁱⁱⁱ	0.93	2.44	3.191 (3)	137
C8—H8···O2^iv	0.93	2.59	3.222 (3)	126

Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) x−1, y, z−1; (iii) −x+1, −y+1, −z; (iv) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[MoF₂O₂(C₁₂H₈N₂)]
M_r	346.14
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	7.5190 (9), 17.818 (2), 9.5331 (11)
β (°)	110.856 (1)
V (Å³)	1193.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.12
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.711, 0.799
No. of measured, independent and observed [I > 2σ(I)] reflections	6460, 2394, 2248
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.621

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.065, 1.04
No. of reflections	2394
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.59

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2001), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Berndt, 1999).

Selected bond lengths (Å) top

Mo1—O2	1.6874 (18)	Mo1—F2	1.9049 (13)
Mo1—O1	1.6936 (17)	Mo1—N2	2.3257 (18)
Mo1—F1	1.9017 (14)	Mo1—N1	2.3295 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2C···F1ⁱ	0.93	2.45	3.202 (3)	137.8
C3—H3C···O1ⁱⁱ	0.93	2.55	3.376 (3)	147.9
C7—H7···F1ⁱⁱⁱ	0.93	2.44	3.191 (3)	137.4
C8—H8···O2^iv	0.93	2.59	3.222 (3)	125.9

Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) x−1, y, z−1; (iii) −x+1, −y+1, −z; (iv) −x+1, y+1/2, −z+1/2.

Acknowledgements

The authors gratefully acknowledge financial support from the Youth Fund of Northeast Normal University.

References

Bingham, A. L., Drake, J. E., Hursthouse, M. B., Light, M. E., Kumar, R. & Ratnani, R. (2006). Polyhedron, 25, 3238–3244. Web of Science CSD CrossRef CAS Google Scholar
Brandenburg, K. & Berndt, M. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2003). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Butcher, R. J., Penfold, B. R. & Slim, E. (1979). J. Chem. Soc. Dalton Trans. pp. 668–675. CSD CrossRef Web of Science Google Scholar
Collison, D., Garner, C. D. & Joule, J. A. (1996). Chem. Soc. Rev. 25, 25–32. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Villata, L. S., Féliz, M. R. & Capparelli, A. L. (2000). Coord. Chem. Rev., 196, 65–84. Web of Science CrossRef CAS Google Scholar
Viossat, B. & Rodier, N. (1979). Acta Cryst. B35, 2715–2718. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Zhou, Y. S., Zhang, L. J., Fun, H. K. & You, X. Z. (2000). Inorg. Chem. Commun. pp. 114–116. Google Scholar