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Acta Cryst. (2007). E63, m2918    [ doi:10.1107/S160053680705461X ]

(2,2'-Bipyridyl)tricarbonyl(di-2-pyridylamine)molybdenum(0) revisited

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

Abstract top

The previous structure report [Howie & McQuillan (1986). J. Chem. Soc. Dalton Trans. pp. 759-764] of the title compound, [Mo(C10H8N2)(C10H9N3)(CO)3], has been corrected. In the present structure, the precision of the Mo-C and Mo-N bond distances for the fac-MoC3N3 centre are significantly improved, and an N atom and a C-H group have been exchanged. Possible intramolecular N-H...C and C-H...N and intermolecular C-H...O interactions are described.

Comment top

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) = 0.0016Å compared to 0.006Å 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.

Related literature top

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).

Experimental top

The title compound was prepared by the method of Howie & McQuillan (1986), to result in dark green facted chunks of (I).

Refinement top

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).

Computing details top

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).

Figures top
[Figure 1] 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.
(2,2'-Bipyridyl)tricarbonyl(di-2-pyridylamine)molybdenum(0) top
Crystal data top
[Mo(C10H8N2)(C10H9N3)(CO)3]F000 = 1024
Mr = 507.36Dx = 1.557 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6454 reflections
a = 10.6273 (4) Åθ = 2.6–25.0º
b = 12.9092 (5) ŵ = 0.64 mm−1
c = 16.5581 (7) ÅT = 298 (2) K
β = 107.728 (1)ºFaceted chunk, dark green
V = 2163.73 (15) Å30.28 × 0.17 × 0.15 mm
Z = 4
Data collection top
Bruker SMART1000 CCD
diffractometer		3811 independent reflections
Radiation source: fine-focus sealed tube3067 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.023
T = 298(2) Kθmax = 25.0º
ω scansθmin = 2.0º
Absorption correction: multi-scan
(SADABS; Bruker, 1999)		h = −12→12
Tmin = 0.841, Tmax = 0.910k = −15→8
12826 measured reflectionsl = −19→19
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difmap and geom
R[F2 > 2σ(F2)] = 0.021H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.061  w = 1/[σ2(Fo2) + (0.0355P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3811 reflectionsΔρmax = 0.26 e Å−3
292 parametersΔρmin = −0.30 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Mo(C10H8N2)(C10H9N3)(CO)3]V = 2163.73 (15) Å3
Mr = 507.36Z = 4
Monoclinic, P21/cMo Kα
a = 10.6273 (4) ŵ = 0.64 mm−1
b = 12.9092 (5) ÅT = 298 (2) K
c = 16.5581 (7) Å0.28 × 0.17 × 0.15 mm
β = 107.728 (1)º
Data collection top
Bruker SMART1000 CCD
diffractometer		3811 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)		3067 reflections with I > 2σ(I)
Tmin = 0.841, Tmax = 0.910Rint = 0.023
12826 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.021292 parameters
wR(F2) = 0.061H atoms treated by a mixture of
independent and constrained refinement
S = 1.06Δρmax = 0.26 e Å−3
3811 reflectionsΔρmin = −0.30 e Å−3
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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Mo10.293621 (15)0.246228 (12)0.062933 (10)0.03100 (7)
C10.4599 (2)0.20447 (19)0.14032 (14)0.0466 (5)
O10.56041 (18)0.17911 (17)0.18766 (11)0.0830 (7)
C20.3533 (2)0.38617 (17)0.09857 (14)0.0441 (5)
O20.39753 (18)0.46686 (13)0.12363 (13)0.0774 (6)
C30.2294 (2)0.23659 (16)0.16098 (15)0.0434 (5)
O30.1968 (2)0.22860 (15)0.22132 (12)0.0708 (5)
C40.4438 (2)0.29588 (18)−0.07405 (13)0.0430 (5)
H40.44500.3628−0.05310.052*
C50.5102 (2)0.2769 (2)−0.13158 (15)0.0514 (6)
H50.55490.3298−0.14940.062*
C60.5094 (2)0.1782 (2)−0.16237 (15)0.0569 (6)
H60.55510.1630−0.20070.068*
C70.4403 (2)0.10208 (18)−0.13597 (14)0.0490 (6)
H70.43740.0351−0.15710.059*
C80.37499 (19)0.12607 (15)−0.07757 (12)0.0359 (4)
C90.29805 (19)0.04888 (15)−0.04587 (12)0.0367 (4)
C100.2805 (2)−0.05268 (17)−0.07389 (16)0.0565 (6)
H100.3158−0.0751−0.11580.068*
C110.2103 (3)−0.1206 (2)−0.03941 (19)0.0695 (8)
H110.1989−0.1893−0.05720.083*
C120.1579 (3)−0.08492 (19)0.02146 (18)0.0646 (7)
H120.1095−0.12880.04540.078*
C130.1779 (2)0.01607 (17)0.04632 (15)0.0492 (6)
H130.14170.03950.08750.059*
C140.0659 (2)0.25571 (15)−0.11820 (13)0.0408 (5)
H140.13420.2228−0.13220.049*
C15−0.0520 (2)0.26647 (17)−0.18039 (14)0.0472 (5)
H15−0.06370.2406−0.23460.057*
C16−0.1531 (2)0.31653 (19)−0.16073 (14)0.0510 (6)
H16−0.23480.3243−0.20160.061*
C17−0.1328 (2)0.35484 (17)−0.08060 (14)0.0445 (5)
H17−0.20000.3896−0.06670.053*
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)
H200.08800.46790.20590.066*
C21−0.0838 (3)0.4944 (2)0.23039 (18)0.0704 (8)
H21−0.04780.52800.28200.084*
C22−0.2169 (3)0.4793 (2)0.1995 (2)0.0757 (9)
H22−0.27310.50290.22890.091*
C23−0.2650 (3)0.4286 (3)0.1243 (2)0.0771 (9)
H23−0.35560.41700.10390.093*
N10.37697 (16)0.22289 (13)−0.04629 (10)0.0338 (4)
N20.24692 (16)0.08371 (12)0.01458 (10)0.0362 (4)
N30.09003 (15)0.28956 (13)−0.03790 (10)0.0334 (4)
N40.02063 (17)0.38006 (14)0.06062 (12)0.0425 (4)
H10.092 (2)0.3747 (18)0.0863 (15)0.051*
N5−0.18931 (19)0.39405 (18)0.07744 (13)0.0613 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mo10.02958 (11)0.03322 (11)0.03088 (11)0.00259 (7)0.01021 (7)−0.00083 (7)
C10.0443 (13)0.0572 (14)0.0381 (12)0.0153 (11)0.0123 (10)−0.0112 (11)
O10.0575 (11)0.1274 (18)0.0493 (10)0.0485 (12)−0.0058 (9)−0.0205 (11)
C20.0337 (12)0.0440 (13)0.0542 (13)0.0039 (10)0.0129 (10)−0.0072 (11)
O20.0640 (12)0.0469 (11)0.1135 (16)−0.0102 (9)0.0157 (11)−0.0252 (11)
C30.0446 (13)0.0456 (13)0.0414 (12)0.0071 (10)0.0152 (10)0.0041 (10)
O30.0838 (14)0.0897 (14)0.0520 (11)0.0104 (10)0.0404 (10)0.0140 (10)
C40.0430 (12)0.0423 (12)0.0446 (12)−0.0060 (10)0.0148 (10)0.0014 (10)
C50.0495 (14)0.0606 (15)0.0492 (14)−0.0088 (11)0.0224 (11)0.0077 (12)
C60.0608 (16)0.0700 (17)0.0523 (15)0.0061 (13)0.0359 (13)0.0064 (13)
C70.0567 (14)0.0491 (13)0.0484 (13)0.0056 (11)0.0267 (11)−0.0032 (11)
C80.0349 (11)0.0383 (11)0.0348 (11)0.0042 (9)0.0111 (9)0.0010 (9)
C90.0379 (11)0.0334 (10)0.0400 (11)0.0035 (8)0.0133 (9)0.0010 (9)
C100.0677 (16)0.0409 (13)0.0696 (16)−0.0010 (12)0.0338 (14)−0.0110 (12)
C110.085 (2)0.0335 (13)0.096 (2)−0.0095 (12)0.0367 (18)−0.0079 (14)
C120.0745 (18)0.0425 (14)0.0856 (19)−0.0114 (12)0.0373 (16)0.0078 (14)
C130.0529 (14)0.0426 (13)0.0602 (14)−0.0023 (10)0.0289 (12)0.0056 (11)
C140.0407 (12)0.0436 (12)0.0388 (12)0.0034 (9)0.0130 (9)0.0007 (10)
C150.0467 (13)0.0551 (14)0.0360 (12)−0.0026 (10)0.0068 (10)−0.0013 (10)
C160.0344 (12)0.0646 (16)0.0466 (13)−0.0024 (11)0.0016 (10)0.0084 (12)
C170.0331 (12)0.0490 (13)0.0512 (13)0.0056 (9)0.0123 (10)0.0047 (11)
C180.0329 (11)0.0283 (10)0.0424 (12)−0.0008 (8)0.0127 (9)0.0009 (9)
C190.0472 (13)0.0297 (11)0.0547 (13)0.0061 (9)0.0237 (11)0.0007 (10)
C200.0629 (16)0.0502 (14)0.0593 (15)−0.0063 (12)0.0282 (13)−0.0088 (12)
C210.094 (2)0.0616 (17)0.0717 (18)−0.0064 (15)0.0492 (17)−0.0165 (14)
C220.085 (2)0.0731 (19)0.090 (2)0.0147 (16)0.0577 (19)−0.0087 (17)
C230.0532 (16)0.097 (2)0.092 (2)0.0115 (15)0.0374 (16)−0.0075 (19)
N10.0320 (9)0.0344 (9)0.0361 (9)−0.0006 (7)0.0123 (7)−0.0003 (7)
N20.0376 (9)0.0333 (9)0.0394 (9)0.0016 (7)0.0145 (8)0.0031 (7)
N30.0317 (9)0.0330 (8)0.0363 (9)−0.0003 (7)0.0116 (7)0.0011 (7)
N40.0336 (10)0.0474 (11)0.0454 (11)0.0060 (9)0.0104 (8)−0.0069 (9)
N50.0445 (12)0.0743 (15)0.0701 (14)0.0044 (10)0.0251 (11)−0.0134 (12)
Geometric parameters (Å, °) top
Mo1—C11.917 (2)C12—H120.9300
Mo1—C21.946 (2)C13—N21.346 (3)
Mo1—C31.947 (2)C13—H130.9300
Mo1—N22.2465 (16)C14—N31.348 (3)
Mo1—N12.2631 (16)C14—C151.365 (3)
Mo1—N32.3626 (16)C14—H140.9300
C1—O11.163 (3)C15—C161.375 (3)
C2—O21.166 (3)C15—H150.9300
C3—O31.158 (3)C16—C171.370 (3)
C4—N11.342 (3)C16—H160.9300
C4—C51.369 (3)C17—C181.389 (3)
C4—H40.9300C17—H170.9300
C5—C61.371 (3)C18—N31.360 (2)
C5—H50.9300C18—N41.376 (3)
C6—C71.376 (3)C19—N51.320 (3)
C6—H60.9300C19—C201.388 (3)
C7—C81.386 (3)C19—N41.393 (3)
C7—H70.9300C20—C211.375 (3)
C8—N11.351 (2)C20—H200.9300
C8—C91.483 (3)C21—C221.363 (4)
C9—N21.353 (2)C21—H210.9300
C9—C101.384 (3)C22—C231.360 (4)
C10—C111.383 (3)C22—H220.9300
C10—H100.9300C23—N51.352 (3)
C11—C121.372 (4)C23—H230.9300
C11—H110.9300N4—H10.75 (2)
C12—C131.364 (3)
C1—Mo1—C284.81 (10)N2—C13—H13118.1
C1—Mo1—C384.86 (9)C12—C13—H13118.1
C2—Mo1—C388.34 (9)N3—C14—C15124.5 (2)
C1—Mo1—N291.96 (8)N3—C14—H14117.8
C2—Mo1—N2172.47 (7)C15—C14—H14117.8
C3—Mo1—N298.16 (7)C14—C15—C16118.2 (2)
C1—Mo1—N189.51 (7)C14—C15—H15120.9
C2—Mo1—N1101.27 (7)C16—C15—H15120.9
C3—Mo1—N1168.40 (7)C17—C16—C15119.7 (2)
N2—Mo1—N171.86 (6)C17—C16—H16120.2
C1—Mo1—N3176.56 (7)C15—C16—H16120.2
C2—Mo1—N397.94 (7)C16—C17—C18119.1 (2)
C3—Mo1—N397.25 (8)C16—C17—H17120.5
N2—Mo1—N385.06 (6)C18—C17—H17120.5
N1—Mo1—N387.93 (6)N3—C18—N4114.60 (17)
O1—C1—Mo1179.6 (2)N3—C18—C17122.26 (18)
O2—C2—Mo1175.0 (2)N4—C18—C17123.12 (18)
O3—C3—Mo1176.8 (2)N5—C19—C20123.0 (2)
N1—C4—C5123.4 (2)N5—C19—N4119.0 (2)
N1—C4—H4118.3C20—C19—N4118.0 (2)
C5—C4—H4118.3C21—C20—C19118.2 (2)
C4—C5—C6118.6 (2)C21—C20—H20120.9
C4—C5—H5120.7C19—C20—H20120.9
C6—C5—H5120.7C22—C21—C20119.8 (3)
C5—C6—C7119.3 (2)C22—C21—H21120.1
C5—C6—H6120.4C20—C21—H21120.1
C7—C6—H6120.4C23—C22—C21118.0 (2)
C6—C7—C8119.4 (2)C23—C22—H22121.0
C6—C7—H7120.3C21—C22—H22121.0
C8—C7—H7120.3N5—C23—C22124.1 (3)
N1—C8—C7121.44 (19)N5—C23—H23118.0
N1—C8—C9115.60 (16)C22—C23—H23118.0
C7—C8—C9122.96 (19)C4—N1—C8117.80 (17)
N2—C9—C10121.29 (19)C4—N1—Mo1123.83 (14)
N2—C9—C8115.31 (17)C8—N1—Mo1117.73 (12)
C10—C9—C8123.40 (18)C13—N2—C9117.56 (18)
C11—C10—C9119.8 (2)C13—N2—Mo1123.65 (14)
C11—C10—H10120.1C9—N2—Mo1118.63 (13)
C9—C10—H10120.1C14—N3—C18116.25 (17)
C12—C11—C10118.8 (2)C14—N3—Mo1118.60 (13)
C12—C11—H11120.6C18—N3—Mo1125.01 (12)
C10—C11—H11120.6C18—N4—C19130.30 (18)
C13—C12—C11118.8 (2)C18—N4—H1114.7 (18)
C13—C12—H12120.6C19—N4—H1114.1 (18)
C11—C12—H12120.6C19—N5—C23116.8 (2)
N2—C13—C12123.8 (2)
C6—C7—C8—N10.4 (3)N3—Mo1—N1—C8−93.96 (14)
C6—C7—C8—C9179.9 (2)C12—C13—N2—C90.5 (3)
N1—C8—C9—N2−4.2 (3)C12—C13—N2—Mo1−174.87 (19)
C7—C8—C9—N2176.34 (19)C10—C9—N2—C13−0.2 (3)
N1—C8—C9—C10177.0 (2)C8—C9—N2—C13−179.04 (18)
C7—C8—C9—C10−2.4 (3)C10—C9—N2—Mo1175.43 (16)
N2—C9—C10—C11−0.5 (4)C8—C9—N2—Mo1−3.4 (2)
C8—C9—C10—C11178.2 (2)C1—Mo1—N2—C1392.67 (18)
C9—C10—C11—C120.9 (4)C3—Mo1—N2—C137.58 (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—C161.0 (3)C1—Mo1—N2—C9−82.70 (15)
C14—C15—C16—C170.7 (3)C3—Mo1—N2—C9−167.79 (15)
C15—C16—C17—C18−0.8 (3)N1—Mo1—N2—C96.14 (14)
C16—C17—C18—N3−0.7 (3)N3—Mo1—N2—C995.57 (14)
C16—C17—C18—N4177.5 (2)C15—C14—N3—C18−2.5 (3)
N5—C19—C20—C21−3.9 (4)C15—C14—N3—Mo1173.32 (16)
N4—C19—C20—C21178.3 (2)N4—C18—N3—C14−176.06 (17)
C19—C20—C21—C221.6 (4)C17—C18—N3—C142.3 (3)
C20—C21—C22—C230.8 (4)N4—C18—N3—Mo18.4 (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—C14123.55 (15)
C5—C4—N1—Mo1170.18 (17)C3—Mo1—N3—C14−147.12 (15)
C7—C8—N1—C40.4 (3)N2—Mo1—N3—C14−49.50 (14)
C9—C8—N1—C4−179.05 (18)N1—Mo1—N3—C1422.46 (14)
C7—C8—N1—Mo1−170.80 (16)C2—Mo1—N3—C18−61.04 (16)
C9—C8—N1—Mo19.7 (2)C3—Mo1—N3—C1828.29 (16)
C1—Mo1—N1—C4−86.90 (18)N2—Mo1—N3—C18125.91 (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—C1919.9 (3)
N3—Mo1—N1—C495.40 (17)N5—C19—N4—C189.2 (3)
C1—Mo1—N1—C883.75 (16)C20—C19—N4—C18−172.9 (2)
C2—Mo1—N1—C8168.36 (14)C20—C19—N5—C233.4 (4)
C3—Mo1—N1—C822.9 (4)N4—C19—N5—C23−178.9 (2)
N2—Mo1—N1—C8−8.48 (13)C22—C23—N5—C19−0.7 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N4—H1···C30.75 (2)2.40 (2)2.978 (3)135 (2)
C17—H17···N50.932.362.902 (3)117
C10—H10···O1i0.932.433.318 (3)160
C16—H16···O1ii0.932.383.305 (3)172
Symmetry codes: (i) −x+1, −y, −z; (ii) x−1, −y+1/2, z−1/2.
Selected geometric parameters (Å) top
Mo1—C11.917 (2)Mo1—N22.2465 (16)
Mo1—C21.946 (2)Mo1—N12.2631 (16)
Mo1—C31.947 (2)Mo1—N32.3626 (16)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N4—H1···C30.75 (2)2.40 (2)2.978 (3)135 (2)
C17—H17···N50.932.362.902 (3)117
C10—H10···O1i0.932.433.318 (3)160
C16—H16···O1ii0.932.383.305 (3)172
Symmetry codes: (i) −x+1, −y, −z; (ii) x−1, −y+1/2, z−1/2.
references
References top

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Braga, S. S., Coelho, A. C., Gonçalves, I. S. & Almeida Paz, F. A. (2007). Acta Cryst. E63, m780–m782.

Bruker (1999). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Chisholm, M. H., Huffman, J. C., Rothwell, I. P., Kress, N. & Woodruff, W. H. (1981). J. Am. Chem. Soc. 103, 4945–4947.

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Muir, K. J., McQuillan, G. P. & Harrison, W. T. A. (2007). Unpublished work.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.