catena-Poly[[tetra­kis­(μ-penta­fluoro­benzoato-κ2O:O′)dimolybdenum(II)]-μ-4,4′-bipyridine-κ2N:N′]

Han, L.-J.

doi:10.1107/S1600536811031734

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages m1235-m1236

doi:10.1107/S1600536811031734

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catena-Poly[[tetrakis(μ-pentafluorobenzoato-κ²O:O′)dimolybdenum(II)]-μ-4,4′-bipyridine-κ²N:N′]

Li-Juan Han ^a ^*

^aDepartment of Chemistry, Tongji University, Shanghai 200092, People's Republic of China
^*Correspondence e-mail: 08hanlij@tongji.edu.cn

(Received 14 July 2011; accepted 5 August 2011; online 17 August 2011)

In the title compound, [Mo₂(C₇F₅O₂)₄(C₁₀H₈N₂)]_n, the molecule forms a paddle-wheel-type structure. Each Mo₂⁴⁺ unit is equatorially coordinated by four pentafluorobenzoate groups, while the axial positions are occupied by two 4,4′-bipyridine molecules. The Mo—Mo bond length of 2.1227 (4) Å is representative of a dimolybdenum quadruple bond. An infinite linear chain parallel to [110] is formed by the Mo₂⁴⁺ unit coordinating axially to the two N atoms of the 4,4′-bipyridine ligand [Mo—N = 2.594 (2) Å]. The crystal packing shows molecules linked together into a three-dimensional network via Mo—N coordination interactions and weak π–π stacking interactions between perfluorophenyl rings [centroid–centroid distance = 3.7280 (3) Å and centroid-to-plane distance = 3.6103 (12) Å between two pentafluorophenyl rings].

Related literature

For background to coordination polymers, see: Batten (2002 ); Kumar et al. (2004 ). For torsion angles about the pentafluorobenzoate anion, see: Reddy et al. (2004 ); Bach et al. (2001 ); For Mo–Mo quadruple bond lengths, see: Cotton et al. (2005 ).

Experimental

Crystal data

[Mo₂(C₇F₅O₂)₄(C₁₀H₈N₂)]
M_r = 1192.34
Triclinic, $[P \overline 1]$
a = 8.8858 (8) Å
b = 9.9311 (9) Å
c = 11.1978 (10) Å
α = 101.158 (1)°
β = 94.697 (1)°
γ = 99.092 (1)°
V = 950.83 (15) Å³
Z = 1
Mo Kα radiation
μ = 0.82 mm⁻¹
T = 293 K
0.20 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.849, T_max = 0.884
4937 measured reflections
3294 independent reflections
3072 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.061
S = 1.01
3294 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Selected bond lengths (Å)

Mo1—O1	2.1124 (17)
Mo1—O6	2.1155 (16)
Mo1—O5	2.1427 (16)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C55—H55A⋯F35	0.93	2.55	3.152 (2)	122
C51—H51A⋯F33ⁱⁱ	0.93	2.78	2.987 (3)	94
Symmetry code: (ii) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811031734/jj2094sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031734/jj2094Isup2.hkl

checkCIF report

Comment top

The design and construction of coordination polymers are of great interest due to their structural topologies and potential application as functional materials (Batten, 2002; Kumar, et al., 2004). Here, we report the synthesis and crystal structure of the coordination polymer [Mo₂(OOCC₆F₅)₄(C₁₀H₈N₂)]_n.

In the title compound, Mo₂(C₇F₅O₂)₄(C₁₀H₈N₂), (I), the molecule forms a paddle-wheel-type structure. Each quadruply bonded Mo₂⁴⁺ unit is equatorially coordinated by four pertafluoro-benzoate (OOCC₆F₅) groups and the axial positions have associated with them two 4, 4-bipyridine molecules (Fig. 1). The Mo–Mo bond length of 2.1227 (4) Å is representative for dimolybdenum quadruple bonds (Cotton et al., 2005). The torsion angles between the C₆F₅ group and the connected chelating ring (Mo₂OCO) are 72.081 (3)°, 75.537 (3)°, 22.059 (3)° and 22.422 (3)°, respectively, and relate to the O···F repulsion within the pentafluoro-benzonate anion (Reddy et al., 2004; Bach et al., 2001). Weak π–π stacking interactions between perfluorophenyl rings also affect the 72.081 (3)° and 75.537 (3)° torsion angles.

An infinite, linear chain coordination polymer is formed by the Mo₂⁴⁺ unit coordinating axially to the two N atoms of the 4, 4-bipyridine ligand [Mo–N distance = 2.5938 (2) Å] (Fig. 2). A one-dimensional linear chain is generated by the π-π stacking between perfluorophenyl rings as viewed along the equatorial position of the Mo–Mo quadruple bonds (Fig. 3), [the center-to-center distance = 3.7280 (3) Å and center-to-plane distance = 3.6103 (0) Å between two pentafluorophenyl rings]. Crystal packing shows molecules linked together into a three-dimensional network (Fig. 4) via Mo–N coordination interactions and perfluorophenyl rings via weak π–π stacking interactions. Weak C–H···F intermolecular interactions further stabilize the crystal structure [(F···H distances = 2.7879 (15) Å].

Related literature top

For background to coordination polymers, see: Batten (2002); Kumar et al. (2004). For torsion angles about the pentafluorobenzoate anion, see: Reddy et al. (2004); Bach et al. (2001); For Mo–Mo quadruple bond lengths, see: Cotton et al. (2005).

Experimental top

4, 4-bipyridine (0.312 g, 2 mmol) was dissolved in dichloromethane (30 ml), and the solution was filtered to a Schelenk tube. Mo₂(OOCC₆F₅)₄ (0.207 g, 0.2 mmol) was dissolved in ethanol (10 ml), resulting in a clear yellow solution. The yellow solution was carefully layered on the top of the Schelenk tube. Solution diffusion at low temperature (in refrigetator) afforded yellow X-ray quality crystals after three days. Yield: 0.190 g (80%). Anal. Calcd. for C₃₈H₈N₂O₈F₂₀Mo₂: C, 38.28; H, 0.68; N, 2.35. Found: C, 38.13; H, 0.53; N, 2.37.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound drawn with displacement ellipsoids at the 30% probability level. All hydrogen atoms have been omitted for clarity.
	Fig. 2. Part of a one-dimensional linear chain formed by a Mo–N coordination bond viewed along the a axis.
	Fig. 3. Part of a one-dimensional linear chain formed by the π–π intermolecular stacking interactions.
	Fig. 4. Molecular packing diagram of (I) with a view along the a axis.

catena-Poly[[tetrakis(µ-pentafluorobenzoato- κ²O:O')dimolybdenum(II)]-µ-4,4'-bipyridine- κ²N:N'] top

Crystal data top

[Mo₂(C₇F₅O₂)₄(C₁₀H₈N₂)]	Z = 1
M_r = 1192.34	F(000) = 578
Triclinic, P1	D_x = 2.082 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8858 (8) Å	Cell parameters from 4122 reflections
b = 9.9311 (9) Å	θ = 2.5–27.6°
c = 11.1978 (10) Å	µ = 0.82 mm⁻¹
α = 101.158 (1)°	T = 293 K
β = 94.697 (1)°	Block, yellow
γ = 99.092 (1)°	0.20 × 0.18 × 0.15 mm
V = 950.83 (15) Å³

Data collection top

Bruker APEXII CCD diffractometer	3294 independent reflections
Radiation source: fine-focus sealed tube	3072 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −8→10
T_min = 0.849, T_max = 0.884	k = −11→11
4937 measured reflections	l = −13→12

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.061	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0323P)² + 0.6373P] where P = (F_o² + 2F_c²)/3
3294 reflections	(Δ/σ)_max = 0.001
316 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Mo₂(C₇F₅O₂)₄(C₁₀H₈N₂)]	γ = 99.092 (1)°
M_r = 1192.34	V = 950.83 (15) Å³
Triclinic, P1	Z = 1
a = 8.8858 (8) Å	Mo Kα radiation
b = 9.9311 (9) Å	µ = 0.82 mm⁻¹
c = 11.1978 (10) Å	T = 293 K
α = 101.158 (1)°	0.20 × 0.18 × 0.15 mm
β = 94.697 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3294 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3072 reflections with I > 2σ(I)
T_min = 0.849, T_max = 0.884	R_int = 0.013
4937 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.061	H-atom parameters constrained
S = 1.01	Δρ_max = 0.32 e Å⁻³
3294 reflections	Δρ_min = −0.47 e Å⁻³
316 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	0.94356 (2)	0.58128 (2)	0.480838 (17)	0.02757 (8)
F11	0.46291 (19)	0.34697 (17)	0.29542 (17)	0.0569 (4)
F12	0.2509 (2)	0.1493 (2)	0.1523 (2)	0.0712 (5)
F13	0.3174 (2)	−0.10294 (19)	0.05942 (18)	0.0682 (5)
F14	0.6015 (2)	−0.15799 (17)	0.11139 (18)	0.0662 (5)
F15	0.81465 (19)	0.03236 (17)	0.25713 (17)	0.0568 (4)
F31	1.0522 (2)	0.7439 (2)	0.89717 (17)	0.0701 (5)
F32	0.9848 (3)	0.8073 (2)	1.13037 (18)	0.0825 (6)
F33	0.7539 (2)	0.6435 (2)	1.20533 (14)	0.0708 (6)
F34	0.5986 (3)	0.4110 (2)	1.05142 (19)	0.0823 (6)
F35	0.6643 (2)	0.3488 (2)	0.81764 (17)	0.0770 (6)
O1	0.75702 (18)	0.43333 (16)	0.38004 (15)	0.0332 (4)
O2	0.87528 (19)	0.26377 (17)	0.42436 (15)	0.0345 (4)
O5	0.85431 (19)	0.59500 (18)	0.65400 (15)	0.0355 (4)
O6	1.03083 (19)	0.58024 (17)	0.31053 (15)	0.0352 (4)
C1	0.7665 (3)	0.3051 (3)	0.3681 (2)	0.0330 (5)
C3	0.8955 (3)	0.5167 (3)	0.7219 (2)	0.0325 (5)
C11	0.6483 (3)	0.1984 (3)	0.2857 (2)	0.0341 (5)
C12	0.5018 (3)	0.2234 (3)	0.2528 (2)	0.0391 (6)
C13	0.3913 (3)	0.1235 (3)	0.1796 (3)	0.0456 (7)
C14	0.4231 (3)	−0.0065 (3)	0.1325 (3)	0.0467 (7)
C15	0.5677 (3)	−0.0340 (3)	0.1609 (2)	0.0437 (6)
C16	0.6762 (3)	0.0656 (3)	0.2357 (2)	0.0382 (6)
C31	0.8594 (3)	0.5460 (3)	0.8527 (2)	0.0346 (5)
C32	0.9392 (3)	0.6610 (3)	0.9340 (2)	0.0428 (6)
C33	0.9070 (4)	0.6945 (3)	1.0538 (2)	0.0497 (7)
C34	0.7909 (3)	0.6100 (3)	1.0917 (2)	0.0480 (7)
C35	0.7115 (3)	0.4929 (3)	1.0133 (3)	0.0502 (7)
C36	0.7458 (3)	0.4611 (3)	0.8941 (2)	0.0437 (6)
N1	0.2434 (3)	0.2426 (2)	0.5169 (2)	0.0434 (5)
C51	0.3883 (4)	0.2800 (3)	0.5640 (2)	0.0498 (7)
H51A	0.4226	0.3727	0.6027	0.060*
C52	0.1981 (3)	0.1097 (3)	0.4617 (3)	0.0555 (8)
H52A	0.0966	0.0810	0.4270	0.067*
C53	0.2934 (3)	0.0113 (3)	0.4527 (3)	0.0540 (8)
H53A	0.2554	−0.0805	0.4130	0.065*
C54	0.4463 (3)	0.0507 (3)	0.5034 (2)	0.0377 (6)
C55	0.4927 (3)	0.1900 (3)	0.5594 (2)	0.0467 (7)
H55A	0.5938	0.2230	0.5938	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mo1	0.03074 (12)	0.03149 (12)	0.02725 (12)	0.01909 (8)	0.00822 (8)	0.00964 (8)
F11	0.0419 (9)	0.0543 (10)	0.0761 (12)	0.0260 (8)	0.0033 (8)	0.0049 (9)
F12	0.0397 (9)	0.0805 (13)	0.0925 (14)	0.0211 (9)	−0.0114 (9)	0.0154 (11)
F13	0.0585 (11)	0.0614 (11)	0.0735 (12)	−0.0033 (9)	−0.0153 (10)	0.0079 (9)
F14	0.0698 (12)	0.0416 (9)	0.0795 (13)	0.0163 (9)	−0.0058 (10)	−0.0049 (9)
F15	0.0458 (9)	0.0479 (9)	0.0739 (12)	0.0251 (8)	−0.0035 (8)	−0.0034 (8)
F31	0.0668 (12)	0.0753 (13)	0.0585 (11)	−0.0139 (10)	0.0155 (9)	0.0085 (9)
F32	0.1018 (17)	0.0801 (14)	0.0504 (11)	0.0059 (12)	0.0050 (11)	−0.0135 (10)
F33	0.0872 (14)	0.1141 (16)	0.0306 (8)	0.0598 (12)	0.0245 (9)	0.0213 (9)
F34	0.0797 (14)	0.1097 (17)	0.0669 (12)	0.0041 (12)	0.0374 (11)	0.0393 (12)
F35	0.0870 (15)	0.0773 (13)	0.0534 (11)	−0.0205 (11)	0.0149 (10)	0.0069 (10)
O1	0.0319 (9)	0.0335 (9)	0.0390 (9)	0.0169 (7)	0.0043 (7)	0.0098 (7)
O2	0.0357 (9)	0.0349 (9)	0.0375 (9)	0.0162 (7)	0.0044 (7)	0.0108 (7)
O5	0.0391 (9)	0.0449 (10)	0.0318 (9)	0.0260 (8)	0.0126 (7)	0.0124 (7)
O6	0.0403 (10)	0.0412 (9)	0.0334 (9)	0.0225 (8)	0.0121 (7)	0.0153 (7)
C1	0.0331 (13)	0.0395 (13)	0.0328 (12)	0.0160 (11)	0.0105 (10)	0.0123 (10)
C3	0.0317 (12)	0.0401 (13)	0.0312 (12)	0.0150 (11)	0.0092 (10)	0.0116 (10)
C11	0.0344 (13)	0.0394 (13)	0.0339 (12)	0.0131 (11)	0.0097 (10)	0.0131 (10)
C12	0.0380 (14)	0.0440 (14)	0.0426 (14)	0.0178 (12)	0.0109 (11)	0.0162 (12)
C13	0.0342 (14)	0.0573 (17)	0.0504 (16)	0.0141 (13)	0.0022 (12)	0.0196 (14)
C14	0.0457 (16)	0.0500 (16)	0.0420 (15)	0.0011 (13)	−0.0020 (13)	0.0126 (13)
C15	0.0505 (16)	0.0375 (14)	0.0441 (15)	0.0117 (12)	0.0056 (13)	0.0079 (12)
C16	0.0351 (13)	0.0423 (14)	0.0419 (14)	0.0151 (11)	0.0053 (11)	0.0132 (11)
C31	0.0365 (13)	0.0452 (14)	0.0298 (12)	0.0206 (11)	0.0109 (10)	0.0128 (11)
C32	0.0408 (15)	0.0538 (16)	0.0387 (14)	0.0140 (13)	0.0112 (12)	0.0141 (12)
C33	0.0576 (18)	0.0579 (17)	0.0334 (14)	0.0234 (15)	0.0003 (13)	0.0008 (13)
C34	0.0540 (17)	0.076 (2)	0.0283 (13)	0.0404 (16)	0.0159 (12)	0.0177 (14)
C35	0.0463 (16)	0.073 (2)	0.0427 (16)	0.0201 (15)	0.0188 (13)	0.0262 (15)
C36	0.0443 (15)	0.0543 (16)	0.0357 (14)	0.0124 (13)	0.0101 (12)	0.0117 (12)
N1	0.0503 (14)	0.0533 (14)	0.0405 (12)	0.0343 (11)	0.0176 (11)	0.0187 (10)
C51	0.0609 (19)	0.0551 (17)	0.0396 (15)	0.0382 (15)	0.0052 (13)	0.0025 (13)
C52	0.0399 (16)	0.0552 (18)	0.084 (2)	0.0259 (14)	0.0165 (15)	0.0281 (17)
C53	0.0416 (16)	0.0402 (15)	0.090 (2)	0.0202 (13)	0.0163 (15)	0.0234 (15)
C54	0.0446 (15)	0.0458 (14)	0.0363 (13)	0.0264 (12)	0.0179 (11)	0.0211 (11)
C55	0.0491 (16)	0.0586 (17)	0.0360 (14)	0.0320 (14)	0.0019 (12)	0.0018 (12)

Geometric parameters (Å, º) top

Mo1—O2ⁱ	2.0955 (17)	C11—C12	1.397 (3)
Mo1—O1	2.1124 (17)	C11—C16	1.398 (3)
Mo1—O6	2.1155 (16)	C12—C13	1.366 (4)
Mo1—Mo1ⁱ	2.1227 (4)	C13—C14	1.379 (4)
Mo1—O5	2.1427 (16)	C14—C15	1.379 (4)
Mo1—N1ⁱⁱ	2.594 (2)	C15—C16	1.362 (4)
F11—C12	1.337 (3)	C31—C32	1.368 (4)
F12—C13	1.335 (3)	C31—C36	1.379 (4)
F13—C14	1.325 (3)	C32—C33	1.383 (4)
F14—C15	1.340 (3)	C33—C34	1.373 (4)
F15—C16	1.338 (3)	C34—C35	1.365 (4)
F31—C32	1.338 (3)	C35—C36	1.381 (4)
F32—C33	1.325 (3)	N1—C51	1.318 (4)
F33—C34	1.333 (3)	N1—C52	1.327 (4)
F34—C35	1.341 (3)	C51—C55	1.383 (4)
F35—C36	1.333 (3)	C51—H51A	0.9300
O1—C1	1.272 (3)	C52—C53	1.385 (4)
O2—C1	1.274 (3)	C52—H52A	0.9300
O2—Mo1ⁱ	2.0955 (17)	C53—C54	1.393 (4)
O5—C3	1.261 (3)	C53—H53A	0.9300
O6—C3ⁱ	1.261 (3)	C54—C55	1.385 (4)
C1—C11	1.480 (3)	C54—C54ⁱⁱⁱ	1.489 (5)
C3—O6ⁱ	1.261 (3)	C55—H55A	0.9300
C3—C31	1.508 (3)

O2ⁱ—Mo1—O1	176.82 (6)	F15—C16—C11	120.6 (2)
O2ⁱ—Mo1—O6	92.90 (7)	C15—C16—C11	122.5 (2)
O1—Mo1—O6	85.79 (7)	C32—C31—C36	118.0 (2)
O2ⁱ—Mo1—Mo1ⁱ	92.41 (4)	C32—C31—C3	119.8 (2)
O1—Mo1—Mo1ⁱ	90.57 (4)	C36—C31—C3	122.2 (2)
O6—Mo1—Mo1ⁱ	93.70 (4)	F31—C32—C31	119.4 (2)
O2ⁱ—Mo1—O5	85.43 (7)	F31—C32—C33	118.7 (3)
O1—Mo1—O5	95.73 (7)	C31—C32—C33	121.9 (3)
O6—Mo1—O5	176.63 (6)	F32—C33—C34	120.4 (3)
Mo1ⁱ—Mo1—O5	89.29 (4)	F32—C33—C32	120.8 (3)
C1—O1—Mo1	117.52 (15)	C34—C33—C32	118.9 (3)
C1—O2—Mo1ⁱ	116.51 (15)	F33—C34—C35	119.8 (3)
C3—O5—Mo1	117.24 (14)	F33—C34—C33	119.8 (3)
C3ⁱ—O6—Mo1	114.32 (14)	C35—C34—C33	120.5 (2)
O1—C1—O2	122.5 (2)	F34—C35—C34	119.9 (3)
O1—C1—C11	119.5 (2)	F34—C35—C36	120.3 (3)
O2—C1—C11	118.0 (2)	C34—C35—C36	119.8 (3)
O5—C3—O6ⁱ	124.7 (2)	F35—C36—C31	119.9 (2)
O5—C3—C31	117.2 (2)	F35—C36—C35	119.0 (3)
O6ⁱ—C3—C31	118.1 (2)	C31—C36—C35	121.0 (3)
C12—C11—C16	115.6 (2)	C51—N1—C52	116.5 (2)
C12—C11—C1	122.4 (2)	N1—C51—C55	124.1 (3)
C16—C11—C1	122.0 (2)	N1—C51—H51A	117.9
F11—C12—C13	117.1 (2)	C55—C51—H51A	117.9
F11—C12—C11	120.6 (2)	N1—C52—C53	123.8 (3)
C13—C12—C11	122.3 (2)	N1—C52—H52A	118.1
F12—C13—C12	121.0 (3)	C53—C52—H52A	118.1
F12—C13—C14	118.7 (3)	C52—C53—C54	119.7 (3)
C12—C13—C14	120.3 (2)	C52—C53—H53A	120.2
F13—C14—C15	120.5 (3)	C54—C53—H53A	120.2
F13—C14—C13	120.6 (3)	C55—C54—C53	116.0 (2)
C15—C14—C13	119.0 (3)	C55—C54—C54ⁱⁱⁱ	122.0 (3)
F14—C15—C16	120.4 (2)	C53—C54—C54ⁱⁱⁱ	122.0 (3)
F14—C15—C14	119.3 (3)	C51—C55—C54	119.9 (3)
C16—C15—C14	120.3 (2)	C51—C55—H55A	120.1
F15—C16—C15	116.8 (2)	C54—C55—H55A	120.1

O6—Mo1—O1—C1	91.22 (16)	C1—C11—C16—F15	−2.7 (4)
Mo1ⁱ—Mo1—O1—C1	−2.45 (16)	C12—C11—C16—C15	−0.8 (4)
O5—Mo1—O1—C1	−91.80 (16)	C1—C11—C16—C15	179.2 (2)
O2ⁱ—Mo1—O5—C3	−89.66 (18)	O5—C3—C31—C32	−72.1 (3)
O1—Mo1—O5—C3	93.32 (18)	O6ⁱ—C3—C31—C32	105.4 (3)
Mo1ⁱ—Mo1—O5—C3	2.82 (18)	O5—C3—C31—C36	107.0 (3)
O2ⁱ—Mo1—O6—C3ⁱ	98.99 (17)	O6ⁱ—C3—C31—C36	−75.6 (3)
O1—Mo1—O6—C3ⁱ	−83.91 (17)	C36—C31—C32—F31	178.7 (2)
Mo1ⁱ—Mo1—O6—C3ⁱ	6.38 (17)	C3—C31—C32—F31	−2.2 (4)
Mo1—O1—C1—O2	7.3 (3)	C36—C31—C32—C33	−1.2 (4)
Mo1—O1—C1—C11	−172.39 (15)	C3—C31—C32—C33	177.9 (2)
Mo1ⁱ—O2—C1—O1	−8.4 (3)	F31—C32—C33—F32	0.9 (4)
Mo1ⁱ—O2—C1—C11	171.27 (15)	C31—C32—C33—F32	−179.3 (3)
Mo1—O5—C3—O6ⁱ	−9.2 (3)	F31—C32—C33—C34	179.8 (2)
Mo1—O5—C3—C31	168.03 (16)	C31—C32—C33—C34	−0.3 (4)
O1—C1—C11—C12	−22.4 (3)	F32—C33—C34—F33	1.7 (4)
O2—C1—C11—C12	157.9 (2)	C32—C33—C34—F33	−177.3 (2)
O1—C1—C11—C16	157.6 (2)	F32—C33—C34—C35	−179.4 (3)
O2—C1—C11—C16	−22.1 (3)	C32—C33—C34—C35	1.7 (4)
C16—C11—C12—F11	−179.9 (2)	F33—C34—C35—F34	−1.1 (4)
C1—C11—C12—F11	0.0 (4)	C33—C34—C35—F34	179.9 (3)
C16—C11—C12—C13	2.0 (4)	F33—C34—C35—C36	177.4 (3)
C1—C11—C12—C13	−178.1 (2)	C33—C34—C35—C36	−1.5 (4)
F11—C12—C13—F12	0.0 (4)	C32—C31—C36—F35	179.4 (2)
C11—C12—C13—F12	178.2 (2)	C3—C31—C36—F35	0.3 (4)
F11—C12—C13—C14	−179.9 (2)	C32—C31—C36—C35	1.3 (4)
C11—C12—C13—C14	−1.8 (4)	C3—C31—C36—C35	−177.8 (2)
F12—C13—C14—F13	1.4 (4)	F34—C35—C36—F35	0.5 (4)
C12—C13—C14—F13	−178.6 (2)	C34—C35—C36—F35	−178.0 (3)
F12—C13—C14—C15	−179.6 (3)	F34—C35—C36—C31	178.6 (3)
C12—C13—C14—C15	0.3 (4)	C34—C35—C36—C31	0.0 (4)
F13—C14—C15—F14	1.7 (4)	C52—N1—C51—C55	−0.3 (4)
C13—C14—C15—F14	−177.2 (3)	C51—N1—C52—C53	0.6 (4)
F13—C14—C15—C16	179.7 (2)	N1—C52—C53—C54	−0.1 (5)
C13—C14—C15—C16	0.8 (4)	C52—C53—C54—C55	−0.7 (4)
F14—C15—C16—F15	−0.7 (4)	C52—C53—C54—C54ⁱⁱⁱ	179.9 (3)
C14—C15—C16—F15	−178.7 (2)	N1—C51—C55—C54	−0.5 (4)
F14—C15—C16—C11	177.5 (2)	C53—C54—C55—C51	1.0 (4)
C14—C15—C16—C11	−0.5 (4)	C54ⁱⁱⁱ—C54—C55—C51	−179.6 (3)
C12—C11—C16—F15	177.3 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C55—H55A···F35	0.93	2.55	3.152 (2)	122
C51—H51A···F33^iv	0.93	2.78	2.987 (3)	94

Symmetry code: (iv) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	[Mo₂(C₇F₅O₂)₄(C₁₀H₈N₂)]
M_r	1192.34
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.8858 (8), 9.9311 (9), 11.1978 (10)
α, β, γ (°)	101.158 (1), 94.697 (1), 99.092 (1)
V (Å³)	950.83 (15)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.82
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.849, 0.884
No. of measured, independent and observed [I > 2σ(I)] reflections	4937, 3294, 3072
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.061, 1.01
No. of reflections	3294
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.47

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Mo1—O1	2.1124 (17)	Mo1—Mo1ⁱ	2.1227 (4)
Mo1—O6	2.1155 (16)	Mo1—O5	2.1427 (16)

O1—C1—C11—C12	−22.4 (3)	O5—C3—C31—C32	−72.1 (3)
O2—C1—C11—C16	−22.1 (3)	O6ⁱ—C3—C31—C36	−75.6 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C55—H55A···F35	0.93	2.55	3.152 (2)	122.40
C51—H51A···F33ⁱⁱ	0.93	2.78	2.987 (3)	93.86

Symmetry code: (ii) −x+1, −y+1, −z+2.

Acknowledgements

This work was supported by the National Natural Scientific Foundation of China (No. 20741004/B010303).

References

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