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ISSN: 2056-9890

2,3,3′,4′-Tetra­methyl­biphen­yl

aWestCHEM, Department of Chemistry, University of Glasgow, University Avenue, Glasgow G12 8QQ, Scotland
*Correspondence e-mail: d.price@chem.gla.ac.uk

(Received 1 July 2005; accepted 13 July 2005; online 20 July 2005)

2,3,3′,4′-Tetra­methyl­biphen­yl, C16H18, was synthesized in a palladium-catalysed boronic acid cross-coupling reaction. In the solid state, these weakly inter­acting unsymmetrical mol­ecules show an apparent dimerization of the ortho-dimethyl­phen­yl groups, a packing motif that is seen in a significant number of other ortho-dimethyl­phen­yl-containing compounds.

Comment

2,3,3′,4′-Tetra­methyl­biphen­yl, (I)[link], has been reported previously as a minor product in an oxidative coupling reaction (Norman et al., 1973[Norman, R. O. C., Thomas, B. & Willson, J. S. (1973). J. Chem. Soc. Perkin Trans. 2, pp. 325-332.]). We obtained (I)[link] in excellent yield using a Suzuki cross-coupling reaction (Miyaura, 2002[Miyaura, N. (2002). Editor. Topics in Current Chemistry, Vol. 219. New York: Springer-Verlag.]). The unsymmetrical mol­ecules of this compound crystallize in the space group P[\overline{1}] with an asymmetric unit consisting of a single mol­ecule (Fig. 1[link]). All bond distances and angles in the mol­ecule are normal. The two benzene rings are twisted by 54.10 (7)° from coplanarity. The mol­ecule adopts a cis conformation in the solid, with all the meth­yl groups to one side of the biphen­yl rings.

[Scheme 1]

Overall, the packing of these unsymmetrical mol­ecules is complex and not easily visualized. However, one inter­molecular motif does stand out; the ortho-dimethyl­phen­yl groups appear to show a certain self-complementarity. Examination of all the inter­molecular contacts reveals that the shortest inter­molecular C⋯C (∼3.7 Å) and C—H⋯ar­yl π inter­actions are associated with this motif (Fig. 2[link]). Both ortho-dimethyl­phen­yl rings show this inter­action, and both have an inversion centre between the inter­acting mol­ecules. The orientation of each meth­yl group is such that one of the H atoms is directed to the midpoint of an ar­yl C C bond. This looks like a weak hydrogen-bonding inter­action. An examination of the Cambridge Structural Database (Version 5.26; Allen, 2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]) was performed to estimate the significance of this motif. We find that 19% of ortho-dimethylar­yl-containing compounds appear to show this motif, having the six C⋯C inter­molecular inter­actions shown in Fig. 2[link] shorter than 4 Å. Analysis of the distribution of torsion angles that correspond to C2—C3—C14—H14A and C3—C2—C13—H13B in (I)[link] was performed on 198 structures showing this inter­action (group 1), and for the remaining 848 structures that do not (group 2). Although the location of H atoms in X-ray crystallography is often problematic, it is common practice to refine this angle even when all else is constrained. Thus, we believe this analysis to be meaningful. Both groups of compounds show peaks in the histograms at 0, 30 and 60°, with an anomalous spike superimposed on a more normal distribution of the peak at 60°, and no statistically significant difference is seen in the distribution of meth­yl group orientations between these two groups (Fig. 3[link]).

These results suggest that the inter­action is not greatly affected by the –CH3 orientation. They do not exclude the idea that a very weak hydrogen-bonding inter­action may exist here. It must also be realised that, in the group 2 stuctures, other inter­action motifs and geometries may give rise to the extra stability of the ∼60° meth­yl group torsion angle.

[Figure 1]
Figure 1
The mol­ecular structure of (I)[link]. Displacement ellipsoids are shown at the 70% probability level.
[Figure 2]
Figure 2
The motif showing the shortest inter­molecular inter­actions in (I)[link]. The key C⋯C distances are shown in red, and one of the four C—C—C—H torsion angles is shown in green.
[Figure 3]
Figure 3
A plot of the distribution of C—C—C—H torsion angles for ortho-dimethyl­phen­yl-containing compounds which appear to show this type of inter­action (group 1: red) and for the group of ortho-dimethyl­phen­yl that do not (group 2: blue). Data taken from 1046 structures in the Cambridge Structural Database.

Experimental

A mixture of 3,4-dimethyl­bromo­benzene (4.400 g, 23.75 mmol), 2,3-dimethyl­phenyl­boronic acid (4.279 g, 28.55 mmol), palladium(II) acetate (0.1334 g, 0.595 mmol), triphenyl­phosphine (0.3889 g, 1.486 mmol), sodium(I) carbonate (5.083 g, 47.55 mmol), acetonitrile (30 ml) and water (30 ml) was heated to reflux for 24 h under an inert nitro­gen atmosphere. The mixture was acidified with dilute HCl to remove the carbonate ions. The reaction mixture was then filtered, and the solvent removed on a rotary evaporator. Distilled water (30 ml) was then added, and the organic product extracted into dichloro­methane (3 × 30 ml). The combined organic extracts were dried over anhydrous MgSO4, filtered and the solvent removed under reduced pressure. The crude product was recrystallized from ethanol (3.856 g, 77.1%). C16H18 requires C 91.37, H 8.63%; found C 91.23, H 8.62%. 13C NMR (400 MHz, CDCl3): δ 142.25 (C1), 140.10 (C7), 137.09 (C3 or C9), 136.09 (C9 or C3), 134.84 (C10), 134.03 (C2), 130.66 (C11), 129.21 (C4), 128.58 (C8), 127.71 (C5), 126.80 (C6 or C12), 125.15 (C12 or C6), 20.73 (CH3), 19.86 (CH3), 19.48 (CH3), 17.02 (CH3); m/z 210.11 [M] (ESMS+); m/z 210.1408 [12C161H18] (high resolution ESMS+); IR ν/cm−1 (KBr): 3160, 3038, 3018, 2995, 2985, 2943, 2920, 2882, 2860, 1502, 1463, 1455, 1380, 1308, 1278, 1243, 1221, 1197, 1180, 1163, 1136, 1110, 1083, 1061, 1045, 1020, 985, 965, 921, 898, 891, 820, 780, 758, 746, 720, 642, 600.

Crystal data
  • C16H18

  • Mr = 210.30

  • Triclinic, [P \overline 1]

  • a = 7.6018 (5) Å

  • b = 7.7685 (5) Å

  • c = 11.6547 (7) Å

  • α = 77.106 (3)°

  • β = 81.047 (3)°

  • γ = 64.506 (3)°

  • V = 604.19 (7) Å3

  • Z = 2

  • Dx = 1.156 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 4912 reflections

  • θ = 0.1–27.5°

  • μ = 0.07 mm−1

  • T = 293 (2) K

  • Prism, colourless

  • 0.45 × 0.16 × 0.14 mm

Data collection
  • Nonius KappaCCD diffractometer

  • ω and φ scans

  • Absorption correction: multi-scan(Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.])Tmin = 0.830, Tmax = 0.991

  • 9018 measured reflections

  • 2731 independent reflections

  • 1819 reflections with I > 2σ(I)

  • Rint = 0.056

  • θmax = 27.4°

  • h = −9 → 9

  • k = −10 → 9

  • l = −15 → 15

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.127

  • S = 1.04

  • 2731 reflections

  • 152 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0567P)2 + 0.0932P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.21 e Å−3

  • Extinction correction: SHELXL97

  • Extinction coefficient: 0.038 (9)

Ar­yl H atoms were placed in ideal positions (C—H = 0.93 Å) and treated as riding, with a common refined Uiso = 0.0259 (17) Å2. Meth­yl H atoms were constrained in rigid groups with free rotation about the C—C bond (C—H = 0.96 Å) and a common refined Uiso = 0.0388 (14) Å2.

Data collection: COLLECT (Nonius, 1997[Nonius (1997). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

2,3,3',4'-Tetramethylbiphenyl, (I), has been reported previously as a minor product in an oxidative coupling reaction (Norman et al., 1973). We obtained (I) in excellent yield using a Suzuki cross-coupling reaction (Miyaura, 2002). The unsymmetrical molecules of this compound crystallize in the space group P1 with an asymmetric unit consisting of a single molecule (Fig. 1). All bond distances and angles in the molecule are normal. The two benzene rings are twisted by 54.10 (7)° from coplanarity. The molecule adopts a cis conformation in the solid, with all the methyl groups to one side of the biphenyl rings.

Overall, the packing of these unsymmetrical molecules is complex and not easily visualized. However, one intermolecular motif does stand out; the ortho-dimethylphenyl groups appear to show a certain self-complementarity. Examination of all the intermolecular contacts reveals that the shortest intermolecular C···C (~3.7 Å) and CH···aryl π interactions are associated with this motif (Fig. 2). Both ortho-dimethylphenyl rings show this interaction, and both have an inversion centre between the interacting molecules. The orientation of each methyl group is such that one of the H atoms is directed to the midpoint of an aryl CC bond. This looks like a weak hydrogen-bonding interaction. An examination of the Cambridge Structural Database (Version 5.26; Allen, 2002) was performed to estimate the significance of this motif. We find that 19% of ortho-dimethylaryl-containing compounds appear to show this motif, having the six C···C intermolecular interactions shown in Fig. 2 shorter than 4 Å. Analysis of the distribution of torsion angles that correspond to C2—C3—C14—H14A and C3—C2—C13—H13B in (I) was performed on 198 structures showing this interaction (group 1), and for the remaining 848 structures that do not (group 2). Although the location of H atoms in X-ray crystallography is often problematic, it is common practice to refine this angle even when all else is constrained. Thus, we believe this analysis to be meaningful. Both groups of compounds show peaks in the histograms at 0, 30 and 60°, with an anomalous spike superimposed on a more normal distribution of the peak at 60°, and no statistically significant difference is seen in the distribution of methyl group orientations between these two groups (Fig. 3).

These results suggest that the interaction is not greatly affected by the –CH3 orientation. They do not exclude the idea that a very weak hydrogen-bonding interaction may exist here. It must also be realised that, in the group 2 stuctures, other interaction motifs and geometries may give rise to the extra stability of the ~60° methyl group torsion angle.

Experimental top

A mixture of 3,4-dimethylbromobenzene (4.400 g, 23.75 mmol), 2,3-dimethylphenylboronic acid (4.279 g, 28.55 mmol), palladium(II) acetate (0.1334 g, 0.595 mmol), triphenylphosphine (0.3889 g, 1.486 mmol), sodium(I) carbonate (5.083 g, 47.55 mmol), acetonitrile (30 ml) and water (30 ml) was heated to reflux for 24 h under an inert nitrogen atmosphere. The mixture was acidified with dilute HCl to remove the carbonate ions. The reaction mixture was then filtered, and the solvent removed on a rotary evaporator. Distilled water (30 ml) was then added, and the organic product extracted into dichloromethane (3 × 30 ml). The combined organic extracts were dried over anhydrous MgSO4, filtered and the solvent removed under reduced pressure. The crude product was recrystallized from ethanol (3.856 g, 77.1%). C16H18 requires C 91.37, H 8.63%; found C 91.23, H 8.62%. 13C NMR (400 MHz, CDCl3): δ 142.25 (C1), 140.10 (C7), 137.09 (C3 or C9), 136.09 (C9 or C3), 134.84 (C10), 134.03 (C2), 130.66 (C11), 129.21 (C4), 128.58 (C8), 127.71 (C5), 126.80 (C6 or C12), 125.15 (C12 or C6), 20.73 (CH3), 19.86 (CH3), 19.48 (CH3), 17.02 (CH3); m/z:210.11 [M] (ESMS+); m/z 210.1408 [12C161H18] (high resolution ESMS+); IR ν/cm-1 (KBr): 3160, 3038, 3018, 2995, 2985, 2943, 2920, 2882, 2860, 1502, 1463, 1455, 1380, 1308, 1278, 1243, 1221, 1197, 1180, 1163, 1136, 1110, 1083, 1061, 1045, 1020, 985, 965, 921, 898, 891, 820, 780, 758, 746, 720, 642, 600.

Refinement top

Aryl H atoms were placed in ideal positions (C—H = 0.93 Å) and treated as riding, with a common refined Uiso = 0.0259 (17) Å2. Methyl H atoms were constrained in rigid groups with free rotation about the C—C bond (C—H = 0.96 Å) and a common refined Uiso = 0.0388 (14) Å2.

Computing details top

Data collection: COLLECT (Nonius, 1997); cell refinement: DENZO/SCALEPACK; data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I). Displacement ellipsoids are shown at the 70% probability level.
[Figure 2] Fig. 2. The motif showing the shortest intermolecular interactions in (I). The key C···C distances are shown in red, and one of the four C—C—C—H torsion angles is shown in green.
[Figure 3] Fig. 3. A plot of the distribution of C—C—C—H torsion angles for ortho-dimethylphenyl-containing compounds which appear to show this type of interaction (group 1: red) and for the group of ortho-dimethylphenyl that do not (group 2: blue). Data taken from 1046 structures in the Cambridge Structural Database.
2,3,3',4'-Tetramethylbiphenyl top
Crystal data top
C16H18Z = 2
Mr = 210.30F(000) = 228
Triclinic, P1Dx = 1.156 Mg m3
Hall symbol: -P 1Melting point: 41 K
a = 7.6018 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.7685 (5) ÅCell parameters from 4912 reflections
c = 11.6547 (7) Åθ = 0.1–27.5°
α = 77.106 (3)°µ = 0.07 mm1
β = 81.047 (3)°T = 293 K
γ = 64.506 (3)°Prism, colourless
V = 604.19 (7) Å30.45 × 0.16 × 0.14 mm
Data collection top
Nonius KappaCCD
diffractometer
2731 independent reflections
Radiation source: fine-focus sealed tube1819 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
ω and ϕ scansθmax = 27.4°, θmin = 1.8°
Absorption correction: multi-scan
(Blessing, 1995)
h = 99
Tmin = 0.830, Tmax = 0.991k = 109
9018 measured reflectionsl = 1515
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.0567P)2 + 0.0932P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2731 reflectionsΔρmax = 0.28 e Å3
152 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.038 (9)
Crystal data top
C16H18γ = 64.506 (3)°
Mr = 210.30V = 604.19 (7) Å3
Triclinic, P1Z = 2
a = 7.6018 (5) ÅMo Kα radiation
b = 7.7685 (5) ŵ = 0.07 mm1
c = 11.6547 (7) ÅT = 293 K
α = 77.106 (3)°0.45 × 0.16 × 0.14 mm
β = 81.047 (3)°
Data collection top
Nonius KappaCCD
diffractometer
2731 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
1819 reflections with I > 2σ(I)
Tmin = 0.830, Tmax = 0.991Rint = 0.056
9018 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.127H-atom parameters constrained
S = 1.04Δρmax = 0.28 e Å3
2731 reflectionsΔρmin = 0.21 e Å3
152 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
xyzUiso*/Ueq
C10.0416 (2)0.76311 (19)0.79774 (12)0.0212 (3)
C60.1272 (2)0.7959 (2)0.74562 (13)0.0249 (4)
H60.12220.80230.66460.0259 (17)*
C70.2222 (2)0.7366 (2)0.71854 (12)0.0216 (3)
C20.0334 (2)0.75530 (19)0.92023 (13)0.0216 (3)
C90.5602 (2)0.5383 (2)0.65895 (13)0.0243 (4)
C30.1433 (2)0.77877 (19)0.98797 (13)0.0223 (4)
C100.5521 (2)0.6757 (2)0.55642 (13)0.0249 (4)
C80.3968 (2)0.5716 (2)0.73800 (13)0.0240 (4)
H80.40390.48070.80630.0259 (17)*
C120.2170 (2)0.8719 (2)0.61679 (13)0.0261 (4)
H120.10350.98370.60160.0259 (17)*
C110.3798 (2)0.8414 (2)0.53772 (13)0.0270 (4)
H110.37350.93420.47050.0259 (17)*
C40.3070 (2)0.8096 (2)0.93287 (13)0.0256 (4)
H40.42320.82430.97790.0259 (17)*
C50.2998 (2)0.8189 (2)0.81191 (14)0.0263 (4)
H50.41040.84040.77610.0259 (17)*
C150.7436 (2)0.3550 (2)0.68240 (14)0.0333 (4)
H15A0.72140.27400.75320.0388 (14)*
H15B0.84850.38730.69170.0388 (14)*
H15C0.77740.28710.61720.0388 (14)*
C130.2088 (2)0.7251 (2)0.98124 (13)0.0251 (4)
H13A0.25540.59951.03030.0388 (14)*
H13B0.17200.82291.02900.0388 (14)*
H13C0.31040.73390.92310.0388 (14)*
C160.7252 (2)0.6461 (2)0.46789 (14)0.0323 (4)
H16A0.69070.75140.40220.0388 (14)*
H16B0.76280.52640.44070.0388 (14)*
H16C0.83230.64160.50440.0388 (14)*
C140.1574 (2)0.7706 (2)1.11946 (13)0.0282 (4)
H14A0.28980.79891.15010.0388 (14)*
H14B0.11800.86441.13560.0388 (14)*
H14C0.07340.64351.15640.0388 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0228 (8)0.0144 (7)0.0258 (8)0.0059 (6)0.0044 (6)0.0038 (6)
C60.0264 (8)0.0215 (8)0.0256 (8)0.0063 (7)0.0059 (6)0.0063 (6)
C70.0217 (8)0.0212 (7)0.0236 (8)0.0075 (6)0.0046 (6)0.0080 (6)
C20.0237 (8)0.0143 (7)0.0273 (8)0.0074 (6)0.0053 (6)0.0031 (6)
C90.0229 (8)0.0237 (8)0.0276 (8)0.0055 (6)0.0081 (6)0.0112 (6)
C30.0252 (8)0.0151 (7)0.0266 (8)0.0086 (6)0.0034 (6)0.0020 (6)
C100.0218 (8)0.0301 (8)0.0251 (8)0.0081 (7)0.0039 (6)0.0129 (6)
C80.0258 (8)0.0211 (7)0.0262 (8)0.0080 (6)0.0077 (6)0.0061 (6)
C120.0230 (8)0.0224 (8)0.0277 (8)0.0022 (6)0.0063 (6)0.0057 (6)
C110.0272 (9)0.0280 (8)0.0229 (8)0.0085 (7)0.0036 (7)0.0033 (6)
C40.0224 (8)0.0220 (8)0.0330 (9)0.0098 (6)0.0008 (6)0.0055 (6)
C50.0229 (8)0.0236 (8)0.0338 (9)0.0083 (6)0.0082 (7)0.0058 (6)
C150.0254 (9)0.0322 (9)0.0374 (10)0.0023 (7)0.0081 (7)0.0119 (7)
C130.0276 (8)0.0243 (8)0.0245 (8)0.0108 (7)0.0049 (6)0.0038 (6)
C160.0260 (9)0.0390 (9)0.0313 (9)0.0088 (7)0.0016 (7)0.0146 (7)
C140.0307 (9)0.0269 (8)0.0283 (8)0.0143 (7)0.0017 (7)0.0022 (6)
Geometric parameters (Å, º) top
C1—C61.404 (2)C9—C101.403 (2)
C1—C21.408 (2)C9—C151.5111 (19)
C1—C71.492 (2)C3—C41.394 (2)
C6—C51.377 (2)C3—C141.508 (2)
C7—C121.391 (2)C10—C111.390 (2)
C7—C81.3983 (19)C10—C161.507 (2)
C2—C31.408 (2)C12—C111.388 (2)
C2—C131.5138 (19)C4—C51.389 (2)
C9—C81.390 (2)
C6—C1—C2119.24 (14)C10—C9—C15120.36 (14)
C6—C1—C7117.23 (13)C4—C3—C2119.58 (13)
C2—C1—C7123.52 (13)C4—C3—C14119.58 (13)
C5—C6—C1121.39 (14)C2—C3—C14120.83 (13)
C12—C7—C8117.57 (14)C11—C10—C9118.47 (14)
C12—C7—C1120.03 (13)C11—C10—C16120.25 (14)
C8—C7—C1122.25 (13)C9—C10—C16121.28 (13)
C1—C2—C3119.34 (13)C9—C8—C7122.40 (14)
C1—C2—C13121.78 (13)C11—C12—C7120.60 (13)
C3—C2—C13118.87 (13)C12—C11—C10121.66 (14)
C8—C9—C10119.29 (13)C5—C4—C3121.24 (14)
C8—C9—C15120.35 (14)C6—C5—C4119.21 (14)

Experimental details

Crystal data
Chemical formulaC16H18
Mr210.30
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.6018 (5), 7.7685 (5), 11.6547 (7)
α, β, γ (°)77.106 (3), 81.047 (3), 64.506 (3)
V3)604.19 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.45 × 0.16 × 0.14
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.830, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
9018, 2731, 1819
Rint0.056
(sin θ/λ)max1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.127, 1.04
No. of reflections2731
No. of parameters152
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.21

Computer programs: COLLECT (Nonius, 1997), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg, 1999), WinGX (Farrugia, 1999).

 

Acknowledgements

The authors are grateful to Dr Andrew Parkin (Glasgow University) for the X-ray data collection.

References

First citationAllen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals
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