organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 8| August 2011| Pages o2090-o2091

2,4,5-Tris(bi­phenyl-2-yl)-1-bromo­benzene

aCentro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, P-4169-007 Porto, Portugal, bREQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, P-4169-007 Porto, Portugal, and cDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland
*Correspondence e-mail: jnlow111@gmail.com

(Received 14 July 2011; accepted 15 July 2011; online 23 July 2011)

In the title compound, C42H29Br, the dihedral angles between the central benzene ring and the three attached benzene rings are very similar, lying in the range 52.65 (6)–57.20 (7)°. Of the dihedral angles between the rings of the o-biphenyl substituents, two are similar [46.34 (7) and 47.35 (7)°], while the other differs significantly [64.17 (7)°]. In the crystal, mol­ecules are linked into centrosymmetric dimers by two weak C—H⋯π inter­actions.

Related literature

For background to the Suzuki–Miyaura cross-coupling reaction in the synthesis of aryl­naphthalenes and polyphenyl­enes, see: Miyaura & Suzuki (1995[Miyaura, N. & Suzuki, A. (1995). Chem. Rev. 95, 2457-2483.]); Liu et al. (2006[Liu, L. Y., Zhang, Y. & Xin, B. (2006). J. Org. Chem. 71, 3994-3997.]); Lima et al. (2011[Lima, C. F. R. A. C., Rodriguez-Borges, J. E. & Santos, L. M. N. B. F. (2011). Tetrahedron, 67, 689-697.]). For crystal structures of related o-polyphenyl­enes, see: Muller et al. (1997[Muller, M., Iyer, V. S., Kubel, C., Enkelmann, V. & Mullen, K. (1997). Angew. Chem. Int. Ed. 36, 1607-1610.]); Iyer et al. (1998[Iyer, V. S., Yoshimura, K., Enkelmann, V., Epsch, R., Rabe, J. P. & Mullen, K. (1998). Angew. Chem. Int. Ed. 37, 2696-2699.]); Nehls et al. (2005[Nehls, B. S., Galbrecht, F., Bilge, A., Brauer, D. J., Lehmann, C. W., Scherf, U. & Farrell, T. (2005). Org. Biomol. Chem. 3, 3213-3219.]).

[Scheme 1]

Experimental

Crystal data
  • C42H29Br

  • Mr = 613.56

  • Triclinic, [P \overline 1]

  • a = 11.6723 (5) Å

  • b = 12.2455 (6) Å

  • c = 12.4859 (6) Å

  • α = 62.549 (2)°

  • β = 70.771 (2)°

  • γ = 79.407 (2)°

  • V = 1494.26 (12) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.41 mm−1

  • T = 150 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.678, Tmax = 0.872

  • 37893 measured reflections

  • 8078 independent reflections

  • 7272 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.027

  • wR(F2) = 0.073

  • S = 1.04

  • 8078 reflections

  • 388 parameters

  • H-atom parameters constrained

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg6 are the centroids of the C21–26 and C421–C426 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C43—H43⋯Cg2i 0.95 2.89 3.7273 (15) 148
C226—H226⋯Cg6i 0.95 2.78 3.6129 (17) 147
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009)[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]; software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The Suzuki-Miyaura reaction, also called Suzuki coupling, is a particular type of cross-coupling reaction that involves the coupling of an organometallic boron species, R—B, with an organic electrophile, R'-X where X is an organic halide (Br in the presented case), in the presence of a Pd catalyst and a base, resulting in the formation of a new C—C bond, (Miyaura & Suzuki, 1995) and (Liu et al., 2006).

The title compound can thus be used as a useful electrophile for insertion of a new substituent on the 1 position of the central ring and it was prepared as a part of the ongoing research concerning about the importance of the transmetallation step in the overall efficiency of the cross-coupling reaction and about the role of the intramolecular Pd···π and π ··· π aromatic interactions on the stabilization of Pd(II) complexes, that contributes to the selectivity of the Suzuki-Miyaura cross-coupling reaction in the synthesis of arylnaphthalenes and polypnenylenes, (Lima et al., 2011).

The molecule, Fig.1, presents a high degree of torsion between phenyl rings probably due to the steric hindrance promoted by the ortho-substitution of the 2-biphenylyl substituents on the central benzene ring. The dihedral angles between the mean plane of the central phenyl ring containing atoms C1 and the mean planes of the phenyl rings attached to atoms C2, C4 and C5 are respectively, 57.20 (7)°, 56.88 (6)° and 52.65 (6)°. The dihedral angle between the phenyl rings containing atoms C21 and C221 is 64.17 (7)°, that between the mean plane of the phenyl rings C containing atoms C41 and C421 is 47.35 (7)°, that between the phenyl rings C containing atoms C51 and C521 is 46.34 (7)° and that between the phenyl rings containing atoms C41 and C51 is 52.21 (7)°.

The molecules are linked to form a centrosymmetric dimer by two weak C—H···π interactions, Table 1 and Fig.2. There are no π···π interactions.

Related literature top

For bckground to the Suzuki–Miyaura cross-coupling reaction in the synthesis of arylnaphthalenes and polyphenylenes, see: Miyaura & Suzuki (1995); Liu et al. (2006); Lima et al. (2011). For crystal structures of related o-polyphenylenes, see: Muller et al. (1997); Iyer et al. (1998); Nehls et al. (2005).

Experimental top

A mixture of 1,2,4,5-tetrabromobenzene (0.35 mmol), 2-boronic acid (1.9 mmol), PdCl2(dppe) (0.07 mmol) and K2CO3 (2.5 mmol) in 35 cm3 of distilled water/toluene (1:2.5) was stirred under nitrogen atmosphere for approximately 10 h at 359 K. Afterwards the reaction mixture was extracted twice with aqueous solutions of NaOH (1M) followed by HCl (1M), respectively. The product was purified by recrystallization from methanol. The sublimation of the compound at reduced pressure (<10 Pa) and T=520 K, produced colorless blocks of the title compound.

Refinement top

H atoms were treated as riding atoms with C—H(aromatic), 0.95 Å, with Uiso = 1.2Ueq(C). The positions of the H atoms were calculated and checked on a difference map during the refinement. Four refections were omitted, two of which were obscured by the beamstop and two for which (Iobs/Ical)/sigma was greater than 10.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of (I) with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. Stereoview of the dimer formed by the pairs of C—H···π interactions. Hydrogen atoms not involved in the motifs are not included.
2,4,5-Tris(biphenyl-2-yl)-1-bromobenzene top
Crystal data top
C42H29BrZ = 2
Mr = 613.56F(000) = 632
Triclinic, P1Dx = 1.364 Mg m3
a = 11.6723 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.2455 (6) ÅCell parameters from 302 reflections
c = 12.4859 (6) Åθ = 3.4–58.4°
α = 62.549 (2)°µ = 1.41 mm1
β = 70.771 (2)°T = 150 K
γ = 79.407 (2)°Block, colorless
V = 1494.26 (12) Å30.30 × 0.20 × 0.10 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
8078 independent reflections
Radiation source: fine-focus sealed tube7272 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 8.33 pixels mm-1θmax = 29.4°, θmin = 2.6°
ω scansh = 1616
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
k = 1616
Tmin = 0.678, Tmax = 0.872l = 1717
37893 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0377P)2 + 0.5752P]
where P = (Fo2 + 2Fc2)/3
8078 reflections(Δ/σ)max = 0.001
388 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C42H29Brγ = 79.407 (2)°
Mr = 613.56V = 1494.26 (12) Å3
Triclinic, P1Z = 2
a = 11.6723 (5) ÅMo Kα radiation
b = 12.2455 (6) ŵ = 1.41 mm1
c = 12.4859 (6) ÅT = 150 K
α = 62.549 (2)°0.30 × 0.20 × 0.10 mm
β = 70.771 (2)°
Data collection top
Bruker SMART APEX CCD
diffractometer
8078 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
7272 reflections with I > 2σ(I)
Tmin = 0.678, Tmax = 0.872Rint = 0.024
37893 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0270 restraints
wR(F2) = 0.073H-atom parameters constrained
S = 1.04Δρmax = 0.45 e Å3
8078 reflectionsΔρmin = 0.32 e Å3
388 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
C10.04428 (10)0.52859 (11)0.66271 (11)0.0180 (2)
Br110.115818 (11)0.483970 (12)0.695774 (14)0.02699 (5)
C20.13584 (11)0.43876 (11)0.69266 (11)0.0170 (2)
C210.12150 (10)0.30322 (11)0.74820 (12)0.0179 (2)
C220.15497 (11)0.22407 (11)0.85852 (12)0.0200 (2)
C2210.19140 (11)0.27166 (11)0.93255 (11)0.0196 (2)
C2220.10917 (12)0.33974 (13)0.99043 (13)0.0266 (3)
H2220.02930.35740.98130.032*
C2230.14269 (15)0.38203 (14)1.06127 (14)0.0320 (3)
H2230.08530.42691.10170.038*
C2240.25946 (15)0.35897 (14)1.07310 (14)0.0323 (3)
H2240.28270.38861.12080.039*
C2250.34230 (14)0.29245 (14)1.01508 (14)0.0311 (3)
H2250.42290.27731.02220.037*
C2260.30824 (12)0.24769 (13)0.94644 (13)0.0254 (3)
H2260.36510.20040.90870.030*
C230.15294 (13)0.09674 (12)0.90096 (14)0.0284 (3)
H230.17580.04280.97530.034*
C240.11824 (14)0.04787 (13)0.83645 (16)0.0321 (3)
H240.11800.03890.86620.038*
C250.08388 (13)0.12577 (13)0.72852 (15)0.0282 (3)
H250.05930.09260.68450.034*
C260.08542 (12)0.25264 (12)0.68466 (13)0.0231 (2)
H260.06170.30570.61060.028*
C30.24967 (10)0.48201 (11)0.66557 (11)0.0167 (2)
H30.31410.42320.68460.020*
C40.27401 (10)0.60642 (11)0.61227 (11)0.0157 (2)
C410.40053 (10)0.63552 (10)0.59165 (11)0.0165 (2)
C420.47576 (11)0.71026 (11)0.47357 (11)0.0172 (2)
C4210.43770 (11)0.76334 (11)0.35645 (11)0.0181 (2)
C4220.38465 (12)0.69133 (12)0.32675 (12)0.0228 (2)
H4220.37210.60670.38230.027*
C4230.35023 (13)0.74304 (14)0.21627 (13)0.0287 (3)
H4230.31400.69350.19690.034*
C4240.36832 (13)0.86627 (15)0.13420 (13)0.0299 (3)
H4240.34390.90140.05920.036*
C4250.42225 (13)0.93801 (13)0.16230 (13)0.0275 (3)
H4250.43511.02250.10620.033*
C4260.45744 (12)0.88690 (12)0.27201 (12)0.0224 (2)
H4260.49540.93640.28990.027*
C430.59232 (11)0.73265 (11)0.46560 (13)0.0214 (2)
H430.64280.78500.38680.026*
C440.63552 (12)0.67984 (12)0.57061 (14)0.0247 (3)
H440.71500.69590.56330.030*
C450.56246 (12)0.60375 (12)0.68599 (13)0.0238 (3)
H450.59200.56650.75790.029*
C460.44577 (11)0.58210 (11)0.69626 (12)0.0201 (2)
H460.39590.53010.77570.024*
C50.17909 (11)0.69510 (11)0.58414 (11)0.0163 (2)
C510.19295 (11)0.83131 (11)0.52144 (11)0.0178 (2)
C520.24172 (11)0.89620 (11)0.56378 (11)0.0190 (2)
C5210.27742 (11)0.83805 (11)0.68262 (12)0.0191 (2)
C5220.38617 (12)0.86815 (12)0.68500 (13)0.0237 (3)
H5220.43790.92400.60960.028*
C5230.41975 (14)0.81785 (13)0.79547 (14)0.0288 (3)
H5230.49450.83840.79520.035*
C5240.34422 (15)0.73745 (14)0.90642 (14)0.0303 (3)
H5240.36700.70280.98230.036*
C5250.23521 (14)0.70788 (13)0.90606 (13)0.0277 (3)
H5250.18300.65340.98210.033*
C5260.20186 (12)0.75741 (12)0.79510 (12)0.0226 (2)
H5260.12720.73630.79580.027*
C530.25388 (13)1.02375 (12)0.49236 (13)0.0243 (3)
H530.28911.06770.51880.029*
C540.21601 (14)1.08736 (12)0.38426 (13)0.0278 (3)
H540.22511.17380.33770.033*
C550.16479 (13)1.02411 (13)0.34442 (13)0.0271 (3)
H550.13711.06710.27140.033*
C560.15443 (12)0.89755 (12)0.41216 (12)0.0220 (2)
H560.12030.85450.38380.026*
C60.06467 (11)0.65329 (11)0.61030 (11)0.0185 (2)
H60.00030.71150.59180.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0140 (5)0.0221 (6)0.0188 (6)0.0031 (4)0.0054 (4)0.0081 (5)
Br110.01578 (6)0.02769 (7)0.03709 (9)0.00372 (5)0.00922 (5)0.01137 (6)
C20.0183 (5)0.0169 (5)0.0154 (5)0.0029 (4)0.0051 (4)0.0057 (4)
C210.0149 (5)0.0178 (5)0.0202 (6)0.0028 (4)0.0035 (4)0.0077 (5)
C220.0181 (5)0.0186 (6)0.0215 (6)0.0013 (4)0.0051 (4)0.0073 (5)
C2210.0226 (6)0.0162 (5)0.0164 (5)0.0011 (4)0.0063 (4)0.0033 (4)
C2220.0233 (6)0.0290 (7)0.0254 (7)0.0011 (5)0.0054 (5)0.0118 (6)
C2230.0408 (8)0.0300 (7)0.0255 (7)0.0021 (6)0.0071 (6)0.0149 (6)
C2240.0488 (9)0.0271 (7)0.0243 (7)0.0052 (6)0.0167 (6)0.0079 (6)
C2250.0326 (7)0.0319 (7)0.0304 (7)0.0005 (6)0.0185 (6)0.0090 (6)
C2260.0250 (6)0.0260 (6)0.0249 (7)0.0048 (5)0.0114 (5)0.0100 (5)
C230.0323 (7)0.0186 (6)0.0311 (7)0.0005 (5)0.0122 (6)0.0064 (5)
C240.0344 (7)0.0191 (6)0.0434 (9)0.0018 (5)0.0110 (6)0.0137 (6)
C250.0248 (6)0.0285 (7)0.0391 (8)0.0039 (5)0.0076 (6)0.0208 (6)
C260.0206 (6)0.0255 (6)0.0259 (6)0.0031 (5)0.0073 (5)0.0120 (5)
C30.0161 (5)0.0167 (5)0.0164 (5)0.0003 (4)0.0060 (4)0.0056 (4)
C40.0156 (5)0.0171 (5)0.0142 (5)0.0019 (4)0.0050 (4)0.0057 (4)
C410.0155 (5)0.0143 (5)0.0208 (6)0.0006 (4)0.0065 (4)0.0076 (4)
C420.0164 (5)0.0156 (5)0.0206 (6)0.0006 (4)0.0053 (4)0.0086 (4)
C4210.0159 (5)0.0188 (5)0.0175 (5)0.0021 (4)0.0018 (4)0.0077 (5)
C4220.0244 (6)0.0237 (6)0.0199 (6)0.0065 (5)0.0026 (5)0.0094 (5)
C4230.0278 (7)0.0389 (8)0.0229 (6)0.0098 (6)0.0053 (5)0.0144 (6)
C4240.0271 (7)0.0396 (8)0.0190 (6)0.0005 (6)0.0070 (5)0.0094 (6)
C4250.0302 (7)0.0230 (6)0.0201 (6)0.0000 (5)0.0040 (5)0.0041 (5)
C4260.0234 (6)0.0194 (6)0.0219 (6)0.0031 (5)0.0032 (5)0.0082 (5)
C430.0167 (5)0.0191 (6)0.0271 (6)0.0029 (4)0.0039 (5)0.0097 (5)
C440.0176 (6)0.0234 (6)0.0376 (7)0.0004 (5)0.0121 (5)0.0141 (6)
C450.0240 (6)0.0214 (6)0.0304 (7)0.0025 (5)0.0166 (5)0.0100 (5)
C460.0216 (6)0.0168 (5)0.0211 (6)0.0007 (4)0.0091 (5)0.0054 (5)
C50.0176 (5)0.0166 (5)0.0149 (5)0.0007 (4)0.0061 (4)0.0059 (4)
C510.0165 (5)0.0163 (5)0.0181 (5)0.0003 (4)0.0049 (4)0.0057 (4)
C520.0197 (5)0.0169 (5)0.0182 (6)0.0006 (4)0.0044 (4)0.0064 (5)
C5210.0241 (6)0.0158 (5)0.0191 (6)0.0014 (4)0.0065 (5)0.0084 (5)
C5220.0274 (6)0.0194 (6)0.0242 (6)0.0057 (5)0.0076 (5)0.0075 (5)
C5230.0325 (7)0.0275 (7)0.0325 (7)0.0055 (5)0.0151 (6)0.0122 (6)
C5240.0410 (8)0.0294 (7)0.0245 (7)0.0038 (6)0.0160 (6)0.0095 (6)
C5250.0342 (7)0.0273 (7)0.0187 (6)0.0072 (5)0.0060 (5)0.0064 (5)
C5260.0254 (6)0.0221 (6)0.0199 (6)0.0048 (5)0.0053 (5)0.0081 (5)
C530.0294 (6)0.0174 (6)0.0238 (6)0.0026 (5)0.0059 (5)0.0075 (5)
C540.0342 (7)0.0158 (6)0.0245 (7)0.0008 (5)0.0068 (5)0.0030 (5)
C550.0301 (7)0.0231 (6)0.0220 (6)0.0040 (5)0.0108 (5)0.0041 (5)
C560.0223 (6)0.0217 (6)0.0212 (6)0.0018 (5)0.0097 (5)0.0071 (5)
C60.0167 (5)0.0199 (6)0.0191 (6)0.0012 (4)0.0073 (4)0.0078 (5)
Geometric parameters (Å, º) top
C1—C61.3879 (17)C423—C4241.386 (2)
C1—C21.3943 (17)C423—H4230.9500
C1—Br111.9027 (11)C424—C4251.387 (2)
C2—C31.3993 (16)C424—H4240.9500
C2—C211.4927 (16)C425—C4261.3867 (19)
C21—C261.3998 (17)C425—H4250.9500
C21—C221.4049 (17)C426—H4260.9500
C22—C231.3986 (18)C43—C441.3875 (19)
C22—C2211.4903 (18)C43—H430.9500
C221—C2261.3921 (18)C44—C451.384 (2)
C221—C2221.3939 (18)C44—H440.9500
C222—C2231.389 (2)C45—C461.3885 (17)
C222—H2220.9500C45—H450.9500
C223—C2241.383 (2)C46—H460.9500
C223—H2230.9500C5—C61.4008 (16)
C224—C2251.384 (2)C5—C511.4944 (16)
C224—H2240.9500C51—C561.4041 (17)
C225—C2261.390 (2)C51—C521.4095 (17)
C225—H2250.9500C52—C531.4032 (17)
C226—H2260.9500C52—C5211.4854 (17)
C23—C241.385 (2)C521—C5261.3968 (17)
C23—H230.9500C521—C5221.3982 (18)
C24—C251.385 (2)C522—C5231.3855 (19)
C24—H240.9500C522—H5220.9500
C25—C261.3904 (19)C523—C5241.387 (2)
C25—H250.9500C523—H5230.9500
C26—H260.9500C524—C5251.387 (2)
C3—C41.3944 (16)C524—H5240.9500
C3—H30.9500C525—C5261.3902 (19)
C4—C51.4115 (16)C525—H5250.9500
C4—C411.4943 (15)C526—H5260.9500
C41—C461.3973 (17)C53—C541.386 (2)
C41—C421.4075 (17)C53—H530.9500
C42—C431.3996 (16)C54—C551.388 (2)
C42—C4211.4845 (17)C54—H540.9500
C421—C4261.3969 (17)C55—C561.3874 (19)
C421—C4221.3971 (17)C55—H550.9500
C422—C4231.3897 (19)C56—H560.9500
C422—H4220.9500C6—H60.9500
C6—C1—C2121.96 (11)C423—C424—C425119.58 (13)
C6—C1—Br11117.21 (9)C423—C424—H424120.2
C2—C1—Br11120.83 (9)C425—C424—H424120.2
C1—C2—C3115.95 (11)C426—C425—C424120.23 (13)
C1—C2—C21125.21 (11)C426—C425—H425119.9
C3—C2—C21118.84 (10)C424—C425—H425119.9
C26—C21—C22119.17 (11)C425—C426—C421120.66 (12)
C26—C21—C2120.24 (11)C425—C426—H426119.7
C22—C21—C2120.32 (11)C421—C426—H426119.7
C23—C22—C21119.07 (12)C44—C43—C42121.28 (12)
C23—C22—C221118.93 (12)C44—C43—H43119.4
C21—C22—C221122.00 (11)C42—C43—H43119.4
C226—C221—C222118.60 (12)C45—C44—C43119.81 (12)
C226—C221—C22120.51 (11)C45—C44—H44120.1
C222—C221—C22120.89 (12)C43—C44—H44120.1
C223—C222—C221120.76 (13)C44—C45—C46119.78 (12)
C223—C222—H222119.6C44—C45—H45120.1
C221—C222—H222119.6C46—C45—H45120.1
C224—C223—C222120.10 (14)C45—C46—C41121.10 (12)
C224—C223—H223119.9C45—C46—H46119.5
C222—C223—H223119.9C41—C46—H46119.5
C223—C224—C225119.67 (14)C6—C5—C4118.00 (11)
C223—C224—H224120.2C6—C5—C51117.08 (10)
C225—C224—H224120.2C4—C5—C51124.82 (10)
C224—C225—C226120.34 (14)C56—C51—C52118.68 (11)
C224—C225—H225119.8C56—C51—C5116.49 (11)
C226—C225—H225119.8C52—C51—C5124.83 (11)
C225—C226—C221120.49 (13)C53—C52—C51118.58 (12)
C225—C226—H226119.8C53—C52—C521117.64 (11)
C221—C226—H226119.8C51—C52—C521123.74 (11)
C24—C23—C22121.17 (13)C526—C521—C522118.38 (12)
C24—C23—H23119.4C526—C521—C52121.52 (11)
C22—C23—H23119.4C522—C521—C52120.03 (11)
C25—C24—C23119.82 (13)C523—C522—C521121.11 (12)
C25—C24—H24120.1C523—C522—H522119.4
C23—C24—H24120.1C521—C522—H522119.4
C24—C25—C26119.90 (13)C522—C523—C524119.96 (13)
C24—C25—H25120.0C522—C523—H523120.0
C26—C25—H25120.0C524—C523—H523120.0
C25—C26—C21120.86 (13)C523—C524—C525119.68 (13)
C25—C26—H26119.6C523—C524—H524120.2
C21—C26—H26119.6C525—C524—H524120.2
C4—C3—C2123.83 (11)C524—C525—C526120.44 (13)
C4—C3—H3118.1C524—C525—H525119.8
C2—C3—H3118.1C526—C525—H525119.8
C3—C4—C5118.86 (10)C525—C526—C521120.42 (12)
C3—C4—C41116.45 (10)C525—C526—H526119.8
C5—C4—C41124.68 (10)C521—C526—H526119.8
C46—C41—C42119.23 (11)C54—C53—C52121.82 (13)
C46—C41—C4117.07 (11)C54—C53—H53119.1
C42—C41—C4123.68 (11)C52—C53—H53119.1
C43—C42—C41118.76 (11)C53—C54—C55119.64 (12)
C43—C42—C421118.64 (11)C53—C54—H54120.2
C41—C42—C421122.58 (10)C55—C54—H54120.2
C426—C421—C422118.75 (12)C56—C55—C54119.43 (13)
C426—C421—C42119.91 (11)C56—C55—H55120.3
C422—C421—C42121.32 (11)C54—C55—H55120.3
C423—C422—C421120.24 (12)C55—C56—C51121.80 (12)
C423—C422—H422119.9C55—C56—H56119.1
C421—C422—H422119.9C51—C56—H56119.1
C424—C423—C422120.52 (13)C1—C6—C5121.40 (11)
C424—C423—H423119.7C1—C6—H6119.3
C422—C423—H423119.7C5—C6—H6119.3
C6—C1—C2—C30.59 (18)C421—C422—C423—C4240.2 (2)
Br11—C1—C2—C3179.28 (9)C422—C423—C424—C4250.6 (2)
C6—C1—C2—C21179.52 (11)C423—C424—C425—C4260.2 (2)
Br11—C1—C2—C211.79 (17)C424—C425—C426—C4210.9 (2)
C1—C2—C21—C2659.25 (17)C422—C421—C426—C4251.63 (19)
C3—C2—C21—C26119.64 (13)C42—C421—C426—C425179.87 (12)
C1—C2—C21—C22126.75 (13)C41—C42—C43—C441.91 (18)
C3—C2—C21—C2254.35 (16)C421—C42—C43—C44176.32 (11)
C26—C21—C22—C230.88 (18)C42—C43—C44—C450.23 (19)
C2—C21—C22—C23173.18 (12)C43—C44—C45—C460.9 (2)
C26—C21—C22—C221178.48 (11)C44—C45—C46—C410.28 (19)
C2—C21—C22—C2217.46 (18)C42—C41—C46—C451.41 (18)
C23—C22—C221—C22663.90 (17)C4—C41—C46—C45179.89 (11)
C21—C22—C221—C226116.74 (14)C3—C4—C5—C60.61 (17)
C23—C22—C221—C222115.38 (15)C41—C4—C5—C6179.22 (11)
C21—C22—C221—C22263.98 (17)C3—C4—C5—C51176.91 (11)
C226—C221—C222—C2230.5 (2)C41—C4—C5—C514.48 (19)
C22—C221—C222—C223178.81 (12)C6—C5—C51—C5651.39 (15)
C221—C222—C223—C2241.3 (2)C4—C5—C51—C56124.94 (13)
C222—C223—C224—C2250.7 (2)C6—C5—C51—C52128.89 (13)
C223—C224—C225—C2260.7 (2)C4—C5—C51—C5254.77 (18)
C224—C225—C226—C2211.6 (2)C56—C51—C52—C532.32 (18)
C222—C221—C226—C2250.9 (2)C5—C51—C52—C53177.39 (12)
C22—C221—C226—C225179.77 (12)C56—C51—C52—C521175.50 (11)
C21—C22—C23—C240.2 (2)C5—C51—C52—C5214.79 (19)
C221—C22—C23—C24179.16 (13)C53—C52—C521—C526131.55 (13)
C22—C23—C24—C250.5 (2)C51—C52—C521—C52646.28 (18)
C23—C24—C25—C260.6 (2)C53—C52—C521—C52245.34 (17)
C24—C25—C26—C210.1 (2)C51—C52—C521—C522136.82 (13)
C22—C21—C26—C250.81 (19)C526—C521—C522—C5231.13 (19)
C2—C21—C26—C25173.25 (12)C52—C521—C522—C523178.12 (12)
C1—C2—C3—C40.18 (18)C521—C522—C523—C5240.9 (2)
C21—C2—C3—C4179.18 (11)C522—C523—C524—C5250.0 (2)
C2—C3—C4—C50.42 (18)C523—C524—C525—C5260.6 (2)
C2—C3—C4—C41179.14 (11)C524—C525—C526—C5210.3 (2)
C3—C4—C41—C4655.82 (15)C522—C521—C526—C5250.56 (19)
C5—C4—C41—C46122.82 (13)C52—C521—C526—C525177.50 (12)
C3—C4—C41—C42122.58 (12)C51—C52—C53—C542.0 (2)
C5—C4—C41—C4258.78 (17)C521—C52—C53—C54175.97 (12)
C46—C41—C42—C432.47 (17)C52—C53—C54—C550.2 (2)
C4—C41—C42—C43179.17 (11)C53—C54—C55—C561.3 (2)
C46—C41—C42—C421175.69 (11)C54—C55—C56—C510.9 (2)
C4—C41—C42—C4212.68 (18)C52—C51—C56—C550.95 (19)
C43—C42—C421—C42647.34 (16)C5—C51—C56—C55178.78 (12)
C41—C42—C421—C426134.51 (12)C2—C1—C6—C50.40 (19)
C43—C42—C421—C422131.12 (13)Br11—C1—C6—C5179.14 (9)
C41—C42—C421—C42247.03 (17)C4—C5—C6—C10.22 (18)
C426—C421—C422—C4231.26 (19)C51—C5—C6—C1176.82 (11)
C42—C421—C422—C423179.74 (12)
Hydrogen-bond geometry (Å, º) top
Cg2 and Cg6 are the centroids of the C21–26 and C421–C426 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C43—H43···Cg2i0.952.893.7273 (15)148
C226—H226···Cg6i0.952.783.6129 (17)147
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC42H29Br
Mr613.56
Crystal system, space groupTriclinic, P1
Temperature (K)150
a, b, c (Å)11.6723 (5), 12.2455 (6), 12.4859 (6)
α, β, γ (°)62.549 (2), 70.771 (2), 79.407 (2)
V3)1494.26 (12)
Z2
Radiation typeMo Kα
µ (mm1)1.41
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.678, 0.872
No. of measured, independent and
observed [I > 2σ(I)] reflections
37893, 8078, 7272
Rint0.024
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.073, 1.04
No. of reflections8078
No. of parameters388
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.45, 0.32

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg2 and Cg6 are the centroids of the C21–26 and C421–C426 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C43—H43···Cg2i0.952.893.7273 (15)148
C226—H226···Cg6i0.952.783.6129 (17)147
Symmetry code: (i) x+1, y+1, z+1.
 

Acknowledgements

Thanks are due to the Fundação para a Ciencia e Tecnologia (FCT) and the Programa Operacional Ciência e Inovação 2010 (POCI 2010) for the financial support of Project POCI/QUI/61873/2004, supported by the European Community Fund FEDER.

References

First citationBruker (2004). APEX, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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First citationLima, C. F. R. A. C., Rodriguez-Borges, J. E. & Santos, L. M. N. B. F. (2011). Tetrahedron, 67, 689–697.  Web of Science CSD CrossRef CAS
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First citationMuller, M., Iyer, V. S., Kubel, C., Enkelmann, V. & Mullen, K. (1997). Angew. Chem. Int. Ed. 36, 1607–1610.  CAS
First citationNehls, B. S., Galbrecht, F., Bilge, A., Brauer, D. J., Lehmann, C. W., Scherf, U. & Farrell, T. (2005). Org. Biomol. Chem. 3, 3213–3219.  Web of Science CSD CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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Volume 67| Part 8| August 2011| Pages o2090-o2091
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