Di-μ-pyridyl-1:2κ2N:C2;2:1κ2N:C2-μ-tetra­hydro­furan-κ2O:O-bis­[bromo­(tetra­hydro­furan)magnesium(II)] tetra­hydro­furan hemisolvate

Churakov, A.V.; Krut'ko, D.P.; Borzov, M.V.; Kirsanov, R.S.; Belov, S.A.; Howard, J.A.K.

doi:10.1107/S1600536806013742

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 62| Part 5| May 2006| Pages m1094-m1096

https://doi.org/10.1107/S1600536806013742

Di-μ-pyridyl-1:2κ²N:C²;2:1κ²N:C²-μ-tetrahydrofuran-κ²O:O-bis[bromo(tetrahydrofuran)magnesium(II)] tetrahydrofuran hemisolvate

Andrei V. Churakov,^a ^* Dmitry P. Krut'ko,^b Maxim V. Borzov,^b Roman S. Kirsanov,^b Sergei A. Belov ^b and Judith A. K. Howard ^c

^aN. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Science, 31 Leninskii Prospect, Moscow 119991, Russian Federation, ^bDepartment of Chemistry, Moscow State University, Leninskie Gory, Moscow 119992, Russian Federation, and ^cDepartment of Chemistry, University of Durham, Science Laboratories, South Road, Durham DH1 3LE, England
^*Correspondence e-mail: churakov@igic.ras.ru

(Received 12 April 2006; accepted 16 April 2006; online 26 April 2006)

The title compound, [Mg₂Br₂(C₅H₄N)₂(C₄H₈O)₃]·0.5C₄H₈O, contains dimeric associations of Mg atoms bridged by tetrahydrofuran (THF) molecules. The coordination polyhedron of the Mg atom is a slightly distorted MgCNO₂Br trigonal bipyramid with two THF molecules in the axial positions. One O atom occupies a site with symmetry 2.

Comment

The main molecule of the title Grignard reagent, (μ-C₄H₈O)[Br(C₄H₈O)(μ-η²-C,N—C₅H₄N-2)Mg]₂, (I) (Fig. 1), is dimeric [Mg1⋯Mg1ⁱ = 3.3237 (18) Å; symmetry code: (i) −y, −x, $[{1\over 2}]$ − z] and is generated by twofold symmetry with O2 lying on a twofold rotation axis. The coordination polyhedron of the Mg atom is a slightly distorted MgCNO₂Br trigonal bipyramid (Table 1) with two tetrahydrofuran (THF) molecules in the axial (ax) positions. Bromine, pyridyl N and C atoms occupy equatorial (eq) sites. The eq—Mg1—eq angles lie within the range 115.52 (11)–121.74 (8)° and the ax—Mg1—eq angles are close to 90° [83.16 (8)–95.07 (10)°].

This coordination environment of Mg is rather characteristic for adducts of Grignard reagents with THF, as was observed for MeMgBr (Vallino, 1969 ) and EtMgCl (Toney & Stucky, 1971 ). The Mg1—Br1, Mg1—O1 and Mg1—C1 bond lengths are normal and consistent with related structures (Cambridge Structural Database; Version 5.27 of January 2006; Allen, 2002 ). The Mg1—N1 distance in (I) is close to that found previously for pyridyl substituted alkylmagnesiumbromide [2.122 (4) Å; Al-Juaid et al., 2001 ].

The sum of valence angles around O1, 358.0°, corresponds to sp²-hybridization. Analysis of data in the CSD showed that the latter is common for structures with Hal—Mg(C)—O(THF, terminal) fragments where the sum of angles varies from 351.8 to 360.0°. The second (O2) THF molecule is bridging and the Mg1—O2—Mg1ⁱ angle is 88.86 (10)° [symmetry code: (i) −y, −x, $[1\over2]$ − z]. As expected, the Mg—O2 bond length is much longer than Mg—O1.

To the best of our knowledge, (I) is only the second example of an Mg complex with a bridging THF molecule. Previously, the dinuclear complex [(THF)(η²-PhNCNPh)]₂Mg₂(μ-Cl)₂(μ-THF), (II), was structurally investigated (Cotton et al., 1997 ); for comparison, the Mg—O(μ-THF) distances in (II) are 2.322 (6) and 2.357 (6) Å, while the Mg—O—Mg angle is 84.3 (2)°. However, the bridging THF ligand is well known in the structures of alkali and rare earth metals complexes; there are 70 entries in the CSD, of which 29 are Li derivatives.

Compound (I) is the first structurally characterized example of an Mg complex with bridging (μ-C,N-pyridyl-2) ligands. However, this bridging ligand is common for di- and polynuclear complexes of other metals (110 entries in the CSD, of which 85 are compounds of 8B group metals).

In the dimeric structure of (I), the Br atoms are terminal. In contrast, an analysis of the CSD demonstrates that in all previously investigated di- and polymeric structures of Grignard reagents, the halogen atoms serve as bridges forming [Mg₂(μ-Hal)₂] fragments (16 entries).

Previously, the synthesis of closely related Grignard reagents (2-pyridyl)MgX·2THF (X = Br and I) was reported and their unit-cell parameters were determined (Paradies, 1974 ). However, no information on their molecular structures was published.

The crystals of (I) contain disordered solvent THF molecules lying on a fourfold axis. These THF molecules occupy the cavities between the main molecules.

Figure 1
Molecular structure of the main molecule of (I)

, showing 50% probability displacement ellipsoids with H atoms omitted for clarity. [Symmetry code: (i) −y, −x, $[{1\over 2}]$ − z.]

Experimental

The synthetic procedure for (I) reported by Paradies & Görbing (1969 ) was found to be non-reproducible. This fact was mentioned by Furukava et al. (1987 ). Compound (I) was prepared by treatment of i-PrMgBr with 2-brompyridine (Trécourt et al., 1999 ) and for the first time isolated in pure form (yield 58%). The crystals of (I) decompose rapidly in open air.

Crystal data

[Mg₂Br₂(C₅H₄N)₂(C₄H₈O)₃]·0.5C₄H₈O
M_r = 616.99
Tetragonal, P 4/n c c
a = 17.3368 (3) Å
c = 18.8696 (4) Å
V = 5671.53 (18) Å³
Z = 8
D_x = 1.445 Mg m⁻³
Mo Kα radiation
μ = 2.93 mm⁻¹
T = 120 (2) K
Block, colourless
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART 1K diffractometer
ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ) T_min = 0.473, T_max = 0.758
30363 measured reflections
3108 independent reflections
2022 reflections with I > 2σ(I)
R_int = 0.093
θ_max = 27.0°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.085
S = 1.00
3108 reflections
161 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0384P)² + 1.9833P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Mg1—Br1	2.4887 (9)
Mg1—O1	2.089 (2)
Mg1—N1	2.129 (3)
Mg1—C1ⁱ	2.149 (3)
Mg1—O2	2.374 (2)

O1—Mg1—N1	93.15 (9)
O1—Mg1—C1ⁱ	95.07 (10)
N1—Mg1—C1ⁱ	115.52 (11)
O1—Mg1—O2	175.18 (8)
N1—Mg1—O2	83.16 (8)
C1ⁱ—Mg1—O2	83.78 (8)
O1—Mg1—Br1	95.02 (6)
N1—Mg1—Br1	121.74 (8)
C1ⁱ—Mg1—Br1	120.98 (8)
O2—Mg1—Br1	89.57 (5)
C6—O2—C6ⁱ	108.2 (3)
C6—O2—Mg1ⁱ	115.36 (12)
C6ⁱ—O2—Mg1ⁱ	114.16 (12)
C6—O2—Mg1	114.16 (12)
C6ⁱ—O2—Mg1	115.36 (12)
Mg1ⁱ—O2—Mg1	88.86 (10)
Symmetry code: (i) $[-y, -x, -z+{\script{1\over 2}}]$ .

The possibility of partial positional disorder of C1 and N1 was checked; no evidence for such disorder was found. The disordered solvent (THF) molecule was refined isotropically with restrained C—C and C—O distances. The position of the O atom in the five-membered ring of the solvent THF molecule was assigned by analysis of isotropic displacement parameters and confirmed by the fact that the methylene group could not be placed in the O22 site without forming unusually short intermolecular H⋯H contacts (1.90–1.94 Å). All H atoms were placed in calculated positions (C—H = 0.95–0.99 Å) and refined using a riding model with U_iso(H) = 1.2U_eq(carrier)

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 2003 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Bruker, 2000 ); software used to prepare material for publication: SHELXTL-Plus.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536806013742/hb2034sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806013742/hb2034Isup2.hkl

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Bruker, 2000); software used to prepare material for publication: SHELXTL-Plus.

Di-µ-pyridyl-1:2κ²N:C²;2:1κ²N:C²-µ-tetrahydrofuran-κ²O:O- bis[bromo(tetrahydrofuran)magnesium(II)] tetrahydrofuran hemisolvate top

Crystal data top

[Mg₂Br₂(C₅H₄N)₂(C₄H₈O)₃]·0.5C₄H₈O	D_x = 1.445 Mg m⁻³
M_r = 616.99	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4/ncc	Cell parameters from 5951 reflections
Hall symbol: -P 4a 2ac	θ = 2.4–27.6°
a = 17.3368 (3) Å	µ = 2.93 mm⁻¹
c = 18.8696 (4) Å	T = 120 K
V = 5671.53 (18) Å³	Block, colourless
Z = 8	0.30 × 0.20 × 0.10 mm
F(000) = 2528

Data collection top

Bruker SMART 1K diffractometer	3108 independent reflections
Radiation source: fine-focus sealed tube	2022 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.093
ω scans	θ_max = 27.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −22→15
T_min = 0.473, T_max = 0.758	k = −20→22
30363 measured reflections	l = −17→24

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0384P)² + 1.9833P] where P = (F_o² + 2F_c²)/3
3108 reflections	(Δ/σ)_max < 0.001
161 parameters	Δρ_max = 0.47 e Å⁻³
6 restraints	Δρ_min = −0.36 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 > 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	Occ. (<1)
Br1	0.00140 (2)	0.130532 (18)	0.410058 (15)	0.03633 (12)
Mg1	0.03748 (6)	0.02350 (5)	0.32866 (5)	0.0227 (2)
N1	−0.02342 (14)	−0.08313 (15)	0.32806 (14)	0.0306 (6)
C1	−0.04365 (15)	−0.11090 (15)	0.26120 (14)	0.0185 (6)
C2	−0.0382 (2)	−0.1275 (2)	0.38650 (18)	0.0391 (8)
H2A	−0.0231	−0.1082	0.4315	0.047*
C3	−0.0731 (2)	−0.1975 (2)	0.3840 (2)	0.0504 (10)
H3A	−0.0842	−0.2252	0.4262	0.060*
C4	−0.0918 (2)	−0.22714 (19)	0.3187 (2)	0.0512 (11)
H4A	−0.1148	−0.2767	0.3148	0.061*
C5	−0.07646 (18)	−0.18353 (19)	0.2586 (2)	0.0408 (9)
H5A	−0.0891	−0.2046	0.2136	0.049*
O1	0.12524 (11)	−0.01943 (12)	0.39346 (11)	0.0297 (5)
C8	0.17086 (19)	−0.08419 (19)	0.36970 (18)	0.0354 (8)
H8A	0.2209	−0.0667	0.3502	0.043*
H8B	0.1431	−0.1139	0.3328	0.043*
C9	0.1827 (2)	−0.1326 (2)	0.4360 (2)	0.0499 (10)
H9A	0.1386	−0.1679	0.4439	0.060*
H9B	0.2308	−0.1633	0.4328	0.060*
C10	0.18817 (19)	−0.0729 (2)	0.49443 (18)	0.0469 (10)
H10A	0.1694	−0.0941	0.5400	0.056*
H10B	0.2420	−0.0551	0.5006	0.056*
C11	0.1372 (2)	−0.0084 (2)	0.46924 (17)	0.0461 (9)
H11A	0.0873	−0.0096	0.4946	0.055*
H11B	0.1622	0.0420	0.4782	0.055*
O2	−0.06215 (10)	0.06215 (10)	0.2500	0.0217 (6)
C6	−0.14031 (16)	0.05431 (17)	0.27933 (16)	0.0256 (7)
H6A	−0.1384	0.0318	0.3275	0.031*
H6B	−0.1722	0.0206	0.2488	0.031*
C7	−0.17336 (18)	0.13479 (18)	0.28166 (16)	0.0339 (8)
H7A	−0.1598	0.1612	0.3265	0.041*
H7B	−0.2302	0.1340	0.2763	0.041*
C21	0.7304 (14)	0.751 (2)	−0.0028 (6)	0.073 (7)*	0.25
H21A	0.6801	0.7243	−0.0069	0.087*	0.25
H21B	0.7420	0.7770	−0.0483	0.087*	0.25
C24	0.7638 (17)	0.7662 (10)	0.1203 (6)	0.064 (6)*	0.25
H24A	0.8090	0.7944	0.1392	0.076*	0.25
H24B	0.7251	0.7604	0.1585	0.076*	0.25
C23	0.7875 (12)	0.6884 (11)	0.0919 (8)	0.066 (5)*	0.25
H23A	0.8383	0.6732	0.1113	0.079*	0.25
H23B	0.7491	0.6487	0.1050	0.079*	0.25
C25	0.7297 (18)	0.8081 (12)	0.0576 (10)	0.111 (10)*	0.25
H25A	0.7609	0.8541	0.0457	0.133*	0.25
H25B	0.6763	0.8248	0.0681	0.133*	0.25
O22	0.7917 (7)	0.6964 (7)	0.0158 (5)	0.065 (3)*	0.25

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0532 (2)	0.03296 (19)	0.02287 (16)	0.01342 (15)	−0.00432 (15)	−0.00763 (14)
Mg1	0.0277 (6)	0.0229 (5)	0.0176 (5)	−0.0017 (4)	0.0006 (4)	−0.0012 (4)
N1	0.0280 (15)	0.0321 (15)	0.0317 (15)	0.0020 (11)	0.0009 (12)	0.0085 (12)
C1	0.0185 (15)	0.0150 (15)	0.0220 (15)	0.0005 (11)	0.0058 (12)	−0.0039 (11)
C2	0.0325 (19)	0.051 (2)	0.0335 (18)	0.0004 (17)	0.0006 (15)	0.0196 (17)
C3	0.038 (2)	0.046 (3)	0.067 (3)	0.0085 (17)	0.017 (2)	0.030 (2)
C4	0.032 (2)	0.0179 (18)	0.103 (4)	0.0012 (14)	0.032 (2)	0.012 (2)
C5	0.033 (2)	0.036 (2)	0.053 (2)	−0.0024 (15)	0.0146 (17)	−0.0169 (17)
O1	0.0308 (12)	0.0336 (13)	0.0246 (11)	0.0063 (9)	−0.0043 (9)	0.0000 (9)
C8	0.0290 (19)	0.037 (2)	0.040 (2)	0.0061 (15)	0.0008 (15)	0.0010 (16)
C9	0.037 (2)	0.042 (2)	0.070 (3)	0.0078 (17)	0.0093 (19)	0.025 (2)
C10	0.033 (2)	0.072 (3)	0.036 (2)	0.0074 (18)	0.0024 (16)	0.0212 (19)
C11	0.057 (2)	0.055 (2)	0.0258 (17)	0.0040 (19)	−0.0140 (16)	0.0038 (17)
O2	0.0206 (9)	0.0206 (9)	0.0238 (15)	0.0000 (11)	0.0027 (8)	0.0027 (8)
C6	0.0174 (16)	0.0322 (18)	0.0273 (16)	−0.0017 (13)	0.0028 (12)	0.0018 (13)
C7	0.0302 (19)	0.038 (2)	0.0336 (19)	0.0065 (15)	−0.0006 (14)	−0.0055 (14)

Geometric parameters (Å, º) top

Mg1—Br1	2.4887 (9)	C10—H10A	0.9900
Mg1—O1	2.089 (2)	C10—H10B	0.9900
Mg1—N1	2.129 (3)	C11—H11A	0.9900
Mg1—C1ⁱ	2.149 (3)	C11—H11B	0.9900
Mg1—O2	2.374 (2)	O2—C6	1.470 (3)
Mg1—Mg1ⁱ	3.3237 (18)	O2—C6ⁱ	1.470 (3)
N1—C2	1.369 (4)	O2—Mg1ⁱ	2.374 (2)
N1—C1	1.395 (3)	C6—C7	1.509 (4)
C1—C5	1.383 (4)	C6—H6A	0.9900
C1—Mg1ⁱ	2.149 (3)	C6—H6B	0.9900
C2—C3	1.356 (5)	C7—C7ⁱ	1.524 (6)
C2—H2A	0.9500	C7—H7A	0.9900
C3—C4	1.373 (5)	C7—H7B	0.9900
C3—H3A	0.9500	C21—O22	1.46 (2)
C4—C5	1.390 (5)	C21—C25	1.511 (19)
C4—H4A	0.9500	C21—H21A	0.9900
C5—H5A	0.9500	C21—H21B	0.9900
O1—C8	1.445 (3)	C24—C23	1.507 (16)
O1—C11	1.458 (4)	C24—C25	1.508 (15)
C8—C9	1.521 (5)	C24—H24A	0.9900
C8—H8A	0.9900	C24—H24B	0.9900
C8—H8B	0.9900	C23—O22	1.444 (16)
C9—C10	1.515 (5)	C23—H23A	0.9900
C9—H9A	0.9900	C23—H23B	0.9900
C9—H9B	0.9900	C25—H25A	0.9900
C10—C11	1.502 (4)	C25—H25B	0.9900

O1—Mg1—N1	93.15 (9)	C9—C10—H10B	111.0
O1—Mg1—C1ⁱ	95.07 (10)	H10A—C10—H10B	109.0
N1—Mg1—C1ⁱ	115.52 (11)	O1—C11—C10	107.3 (3)
O1—Mg1—O2	175.18 (8)	O1—C11—H11A	110.3
N1—Mg1—O2	83.16 (8)	C10—C11—H11A	110.3
C1ⁱ—Mg1—O2	83.78 (8)	O1—C11—H11B	110.3
O1—Mg1—Br1	95.02 (6)	C10—C11—H11B	110.3
N1—Mg1—Br1	121.74 (8)	H11A—C11—H11B	108.5
C1ⁱ—Mg1—Br1	120.98 (8)	C6—O2—C6ⁱ	108.2 (3)
O2—Mg1—Br1	89.57 (5)	C6—O2—Mg1ⁱ	115.36 (12)
O1—Mg1—Mg1ⁱ	129.87 (6)	C6ⁱ—O2—Mg1ⁱ	114.16 (12)
N1—Mg1—Mg1ⁱ	63.98 (7)	C6—O2—Mg1	114.16 (12)
C1ⁱ—Mg1—Mg1ⁱ	62.31 (8)	C6ⁱ—O2—Mg1	115.36 (12)
O2—Mg1—Mg1ⁱ	45.57 (5)	Mg1ⁱ—O2—Mg1	88.86 (10)
Br1—Mg1—Mg1ⁱ	135.11 (2)	O2—C6—C7	106.0 (2)
C2—N1—C1	119.2 (3)	O2—C6—H6A	110.5
C2—N1—Mg1	125.2 (2)	C7—C6—H6A	110.5
C1—N1—Mg1	115.41 (18)	O2—C6—H6B	110.5
C5—C1—N1	116.8 (3)	C7—C6—H6B	110.5
C5—C1—Mg1ⁱ	125.3 (2)	H6A—C6—H6B	108.7
N1—C1—Mg1ⁱ	117.92 (18)	C6—C7—C7ⁱ	102.49 (18)
C3—C2—N1	123.9 (4)	C6—C7—H7A	111.3
C3—C2—H2A	118.0	C7ⁱ—C7—H7A	111.3
N1—C2—H2A	118.0	C6—C7—H7B	111.3
C2—C3—C4	118.1 (3)	C7ⁱ—C7—H7B	111.3
C2—C3—H3A	120.9	H7A—C7—H7B	109.2
C4—C3—H3A	120.9	O22—C21—C25	104.4 (13)
C3—C4—C5	118.9 (3)	O22—C21—H21A	110.9
C3—C4—H4A	120.5	C25—C21—H21A	110.9
C5—C4—H4A	120.5	O22—C21—H21B	110.9
C1—C5—C4	123.0 (3)	C25—C21—H21B	110.9
C1—C5—H5A	118.5	H21A—C21—H21B	108.9
C4—C5—H5A	118.5	C23—C24—C25	105.0 (9)
C8—O1—C11	109.2 (2)	C23—C24—H24A	110.7
C8—O1—Mg1	119.60 (18)	C25—C24—H24A	110.7
C11—O1—Mg1	129.16 (18)	C23—C24—H24B	110.7
O1—C8—C9	104.3 (3)	C25—C24—H24B	110.7
O1—C8—H8A	110.9	H24A—C24—H24B	108.8
C9—C8—H8A	110.9	O22—C23—C24	106.3 (11)
O1—C8—H8B	110.9	O22—C23—H23A	110.5
C9—C8—H8B	110.9	C24—C23—H23A	110.5
H8A—C8—H8B	108.9	O22—C23—H23B	110.5
C10—C9—C8	103.3 (3)	C24—C23—H23B	110.5
C10—C9—H9A	111.1	H23A—C23—H23B	108.7
C8—C9—H9A	111.1	C24—C25—C21	105.8 (11)
C10—C9—H9B	111.1	C24—C25—H25A	110.6
C8—C9—H9B	111.1	C21—C25—H25A	110.6
H9A—C9—H9B	109.1	C24—C25—H25B	110.6
C11—C10—C9	104.0 (3)	C21—C25—H25B	110.6
C11—C10—H10A	111.0	H25A—C25—H25B	108.7
C9—C10—H10A	111.0	C23—O22—C21	105.3 (12)
C11—C10—H10B	111.0

Symmetry code: (i) −y, −x, −z+1/2.

Acknowledgements

The authors thank the RFBR for financial support (grant 04-03-32288). AVC is grateful to the Russian Science Support Foundation.

References

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Volume 62| Part 5| May 2006| Pages m1094-m1096

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