organic compounds
1-Bromo-3,5-diphenylbenzene
aCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, People's Republic of China, bLibrary of Luoyang Normal University, Luoyang 471022, People's Republic of China, and cLiming Research Institute of Chemical Industry, Luoyang 471001, People's Republic of China
*Correspondence e-mail: lyhxxjbm@126.com.cn
The title compound, C18H13Br, crystallizes with two crystallographically independent molecules in the The C—Br bond lengths and the C—C bond lengths between the benzene rings are slightly different in the two molecules. The dihedral angles between adjacent benzene rings are 26.85 (2) and 39.99 (2)° in one molecule, and 29.90 (2) and 38.01 (2)° in the other. There are three types of intermolecular C—H⋯π interactions in the crystal structure.
Related literature
For blue light-emitting diodes based on 3,5-diaryl-phenyl derivatives, see: Niu et al. (2004). For the synthesis of the title compound, see: Kim et al. (2001). For the importance of C—H⋯π contacts and their geometries, see, for example: Suezawa et al. (2004).
Experimental
Crystal data
|
Data collection: SMART (Bruker, 2004); cell SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536809045061/si2218sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809045061/si2218Isup2.hkl
The title compound was synthesized according to the reported procedure (Kim, et al., 2001). A mixture of phenylboronic acid (0.49 g, 4 mmol), 1,3, 5-tribromobenzene (0.63 g, 2 mmol) and Pd(PPh3)4 (20 mg) was added 20 ml tetrahydrofuran and 8 ml aqueous potassium carbonate (2 M). The mixture was vigorously refluxed under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature, and then extracted by ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. After removing the solvent in vacuum, the crude product was purified by
using petroleum ether as The title compound was obtained in 54% yield. The single crystals suitable for the X-ray crystallographic analysis were obtained by slow evaporation of a dichloromethane solution as colorless blocks.All of the H atoms were positioned geometrically with C—H of 0.93 Å and were constrained in a riding motion on their parent carbon atoms with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 2004); cell
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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The two independent molecules of the title compound with labelled non-hydrogen atoms using 30% probability ellipsoids. |
C18H13Br | F(000) = 624 |
Mr = 309.19 | Dx = 1.494 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.0782 (12) Å | Cell parameters from 3281 reflections |
b = 7.7495 (8) Å | θ = 2.7–24.8° |
c = 16.7782 (17) Å | µ = 2.97 mm−1 |
β = 107.441 (1)° | T = 294 K |
V = 1374.2 (2) Å3 | Block, colourless |
Z = 4 | 0.41 × 0.13 × 0.09 mm |
Bruker SMART APEX CCD area-detector diffractometer | 4775 independent reflections |
Radiation source: fine-focus sealed tube | 4138 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
ϕ and ω scans | θmax = 25.5°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.375, Tmax = 0.776 | k = −9→8 |
7808 measured reflections | l = −20→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.0488P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
4775 reflections | Δρmax = 0.23 e Å−3 |
343 parameters | Δρmin = −0.31 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 2006 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.007 (7) |
C18H13Br | V = 1374.2 (2) Å3 |
Mr = 309.19 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 11.0782 (12) Å | µ = 2.97 mm−1 |
b = 7.7495 (8) Å | T = 294 K |
c = 16.7782 (17) Å | 0.41 × 0.13 × 0.09 mm |
β = 107.441 (1)° |
Bruker SMART APEX CCD area-detector diffractometer | 4775 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4138 reflections with I > 2σ(I) |
Tmin = 0.375, Tmax = 0.776 | Rint = 0.014 |
7808 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.076 | Δρmax = 0.23 e Å−3 |
S = 1.00 | Δρmin = −0.31 e Å−3 |
4775 reflections | Absolute structure: Flack (1983), 2006 Friedel pairs |
343 parameters | Absolute structure parameter: 0.007 (7) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.21282 (3) | 0.79871 (5) | 0.29748 (2) | 0.05470 (12) | |
Br2 | −0.04494 (4) | 0.42942 (6) | 0.31148 (2) | 0.06496 (14) | |
C1 | 0.4329 (3) | 0.2381 (4) | 0.3577 (2) | 0.0400 (8) | |
C2 | 0.4454 (3) | 0.1460 (5) | 0.4312 (2) | 0.0484 (9) | |
H2 | 0.3732 | 0.1084 | 0.4434 | 0.058* | |
C3 | 0.5632 (4) | 0.1100 (5) | 0.4859 (2) | 0.0594 (11) | |
H3 | 0.5697 | 0.0484 | 0.5346 | 0.071* | |
C4 | 0.6707 (4) | 0.1645 (6) | 0.4690 (3) | 0.0624 (11) | |
H4 | 0.7498 | 0.1392 | 0.5060 | 0.075* | |
C5 | 0.6613 (4) | 0.2561 (5) | 0.3976 (2) | 0.0587 (11) | |
H5 | 0.7342 | 0.2928 | 0.3860 | 0.070* | |
C6 | 0.5430 (3) | 0.2944 (6) | 0.3424 (2) | 0.0498 (8) | |
H6 | 0.5375 | 0.3587 | 0.2947 | 0.060* | |
C7 | 0.3069 (3) | 0.2758 (5) | 0.29839 (19) | 0.0396 (7) | |
C8 | 0.2064 (3) | 0.3218 (5) | 0.3282 (2) | 0.0430 (8) | |
H8 | 0.2173 | 0.3294 | 0.3852 | 0.052* | |
C9 | 0.0902 (3) | 0.3555 (4) | 0.2707 (2) | 0.0427 (9) | |
C10 | 0.0688 (3) | 0.3457 (4) | 0.1861 (2) | 0.0407 (8) | |
H10 | −0.0110 | 0.3693 | 0.1496 | 0.049* | |
C11 | 0.1686 (3) | 0.2998 (5) | 0.15494 (18) | 0.0350 (6) | |
C12 | 0.2857 (3) | 0.2664 (4) | 0.21181 (19) | 0.0387 (8) | |
H12 | 0.3527 | 0.2366 | 0.1919 | 0.046* | |
C13 | 0.1478 (3) | 0.2884 (5) | 0.06339 (18) | 0.0354 (7) | |
C14 | 0.2206 (3) | 0.1799 (4) | 0.0303 (2) | 0.0389 (7) | |
H14 | 0.2843 | 0.1142 | 0.0661 | 0.047* | |
C15 | 0.1998 (3) | 0.1679 (5) | −0.0555 (2) | 0.0443 (8) | |
H15 | 0.2501 | 0.0958 | −0.0765 | 0.053* | |
C16 | 0.1048 (3) | 0.2626 (5) | −0.1094 (2) | 0.0443 (9) | |
H16 | 0.0896 | 0.2526 | −0.1668 | 0.053* | |
C17 | 0.0325 (3) | 0.3720 (5) | −0.0781 (2) | 0.0451 (9) | |
H17 | −0.0309 | 0.4375 | −0.1143 | 0.054* | |
C18 | 0.0537 (3) | 0.3850 (4) | 0.0076 (2) | 0.0420 (8) | |
H18 | 0.0041 | 0.4595 | 0.0281 | 0.050* | |
C19 | 0.3980 (3) | 0.7771 (4) | 0.03861 (19) | 0.0349 (7) | |
C20 | 0.4802 (3) | 0.8546 (4) | 0.0009 (2) | 0.0390 (8) | |
H20 | 0.5522 | 0.9104 | 0.0338 | 0.047* | |
C21 | 0.4564 (3) | 0.8499 (4) | −0.0852 (2) | 0.0442 (9) | |
H21 | 0.5125 | 0.9019 | −0.1094 | 0.053* | |
C22 | 0.3502 (3) | 0.7685 (5) | −0.1344 (2) | 0.0452 (8) | |
H22 | 0.3344 | 0.7654 | −0.1920 | 0.054* | |
C23 | 0.2669 (3) | 0.6914 (4) | −0.0988 (2) | 0.0431 (8) | |
H23 | 0.1948 | 0.6369 | −0.1324 | 0.052* | |
C24 | 0.2907 (3) | 0.6950 (4) | −0.0130 (2) | 0.0399 (8) | |
H24 | 0.2344 | 0.6420 | 0.0107 | 0.048* | |
C25 | 0.4238 (3) | 0.7824 (4) | 0.13106 (18) | 0.0364 (7) | |
C26 | 0.3245 (3) | 0.7809 (5) | 0.16629 (19) | 0.0390 (7) | |
H26 | 0.2412 | 0.7743 | 0.1321 | 0.047* | |
C27 | 0.3501 (3) | 0.7894 (5) | 0.25135 (19) | 0.0408 (7) | |
C28 | 0.4727 (3) | 0.7964 (5) | 0.30482 (18) | 0.0427 (7) | |
H28 | 0.4875 | 0.8016 | 0.3623 | 0.051* | |
C29 | 0.5735 (3) | 0.7955 (5) | 0.27097 (18) | 0.0383 (7) | |
C30 | 0.5467 (3) | 0.7882 (5) | 0.18430 (18) | 0.0383 (7) | |
H30 | 0.6135 | 0.7871 | 0.1614 | 0.046* | |
C31 | 0.7054 (3) | 0.8081 (5) | 0.32689 (19) | 0.0407 (7) | |
C32 | 0.7968 (3) | 0.9055 (5) | 0.3053 (2) | 0.0488 (9) | |
H32 | 0.7755 | 0.9609 | 0.2538 | 0.059* | |
C33 | 0.9172 (3) | 0.9211 (6) | 0.3584 (3) | 0.0634 (11) | |
H33 | 0.9761 | 0.9888 | 0.3433 | 0.076* | |
C34 | 0.9512 (4) | 0.8367 (6) | 0.4342 (3) | 0.0693 (13) | |
H34 | 1.0332 | 0.8467 | 0.4701 | 0.083* | |
C35 | 0.8638 (4) | 0.7381 (6) | 0.4565 (3) | 0.0625 (11) | |
H35 | 0.8865 | 0.6809 | 0.5075 | 0.075* | |
C36 | 0.7424 (4) | 0.7236 (5) | 0.4036 (2) | 0.0515 (9) | |
H36 | 0.6841 | 0.6561 | 0.4194 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0503 (2) | 0.0711 (3) | 0.0487 (2) | −0.0041 (2) | 0.02380 (16) | −0.0006 (2) |
Br2 | 0.0576 (2) | 0.0860 (3) | 0.0622 (3) | 0.0117 (2) | 0.0346 (2) | −0.0023 (2) |
C1 | 0.0496 (19) | 0.0374 (18) | 0.0336 (18) | 0.0041 (14) | 0.0131 (16) | −0.0058 (13) |
C2 | 0.057 (2) | 0.050 (2) | 0.039 (2) | 0.0019 (18) | 0.0156 (18) | −0.0019 (16) |
C3 | 0.076 (3) | 0.056 (3) | 0.039 (2) | 0.011 (2) | 0.007 (2) | −0.0004 (18) |
C4 | 0.054 (2) | 0.071 (3) | 0.052 (2) | 0.007 (2) | 0.001 (2) | −0.010 (2) |
C5 | 0.046 (2) | 0.071 (3) | 0.055 (2) | 0.0002 (19) | 0.0093 (19) | −0.008 (2) |
C6 | 0.053 (2) | 0.053 (2) | 0.0430 (19) | 0.001 (2) | 0.0147 (16) | −0.003 (2) |
C7 | 0.0467 (18) | 0.035 (2) | 0.0392 (17) | −0.0043 (16) | 0.0157 (15) | −0.0042 (15) |
C8 | 0.0509 (19) | 0.044 (2) | 0.0390 (17) | −0.0037 (17) | 0.0204 (16) | −0.0053 (16) |
C9 | 0.046 (2) | 0.043 (2) | 0.048 (2) | 0.0015 (14) | 0.0255 (17) | −0.0040 (15) |
C10 | 0.0348 (16) | 0.042 (2) | 0.046 (2) | −0.0021 (13) | 0.0127 (15) | −0.0006 (14) |
C11 | 0.0390 (16) | 0.0285 (15) | 0.0383 (16) | 0.0006 (16) | 0.0130 (13) | −0.0014 (15) |
C12 | 0.0390 (17) | 0.040 (2) | 0.0390 (18) | 0.0007 (14) | 0.0152 (15) | −0.0003 (15) |
C13 | 0.0344 (15) | 0.0317 (16) | 0.0408 (17) | −0.0086 (15) | 0.0120 (13) | −0.0023 (16) |
C14 | 0.0376 (17) | 0.0400 (19) | 0.0378 (18) | 0.0032 (14) | 0.0093 (15) | −0.0008 (15) |
C15 | 0.0437 (19) | 0.047 (2) | 0.045 (2) | −0.0006 (17) | 0.0181 (17) | −0.0066 (17) |
C16 | 0.0475 (19) | 0.051 (2) | 0.0343 (18) | −0.0076 (16) | 0.0120 (15) | 0.0008 (16) |
C17 | 0.0415 (19) | 0.050 (2) | 0.039 (2) | −0.0005 (15) | 0.0043 (16) | 0.0077 (15) |
C18 | 0.0348 (17) | 0.046 (2) | 0.044 (2) | 0.0011 (15) | 0.0105 (16) | −0.0012 (16) |
C19 | 0.0345 (15) | 0.0327 (18) | 0.0365 (16) | 0.0045 (14) | 0.0090 (13) | −0.0003 (15) |
C20 | 0.0361 (17) | 0.0402 (19) | 0.0397 (19) | −0.0039 (13) | 0.0101 (15) | −0.0033 (14) |
C21 | 0.049 (2) | 0.045 (2) | 0.042 (2) | 0.0008 (15) | 0.0178 (17) | −0.0013 (15) |
C22 | 0.0492 (19) | 0.051 (2) | 0.0331 (17) | 0.0039 (17) | 0.0098 (15) | −0.0032 (16) |
C23 | 0.0400 (18) | 0.047 (2) | 0.0370 (19) | −0.0033 (16) | 0.0034 (15) | −0.0100 (16) |
C24 | 0.0369 (17) | 0.041 (2) | 0.0422 (19) | −0.0048 (14) | 0.0129 (15) | −0.0010 (15) |
C25 | 0.0424 (16) | 0.0324 (18) | 0.0341 (16) | 0.0006 (15) | 0.0108 (13) | −0.0039 (15) |
C26 | 0.0380 (16) | 0.0408 (19) | 0.0377 (17) | −0.0023 (15) | 0.0109 (13) | −0.0021 (16) |
C27 | 0.0452 (18) | 0.0381 (18) | 0.0427 (18) | −0.0019 (17) | 0.0185 (15) | 0.0014 (17) |
C28 | 0.0517 (19) | 0.0433 (18) | 0.0331 (17) | 0.0034 (19) | 0.0129 (15) | 0.0026 (18) |
C29 | 0.0411 (16) | 0.0335 (16) | 0.0376 (16) | 0.0008 (16) | 0.0079 (13) | −0.0056 (16) |
C30 | 0.0373 (17) | 0.0397 (18) | 0.0393 (17) | 0.0037 (16) | 0.0138 (14) | 0.0002 (18) |
C31 | 0.0447 (18) | 0.0406 (19) | 0.0341 (17) | 0.0114 (19) | 0.0078 (14) | −0.0039 (18) |
C32 | 0.0439 (19) | 0.051 (2) | 0.048 (2) | 0.0030 (18) | 0.0086 (17) | 0.0031 (18) |
C33 | 0.044 (2) | 0.066 (3) | 0.074 (3) | −0.002 (2) | 0.008 (2) | −0.012 (3) |
C34 | 0.049 (2) | 0.075 (3) | 0.065 (3) | 0.016 (2) | −0.012 (2) | −0.022 (2) |
C35 | 0.068 (3) | 0.067 (3) | 0.044 (2) | 0.017 (2) | 0.003 (2) | −0.0024 (19) |
C36 | 0.055 (2) | 0.054 (2) | 0.039 (2) | 0.0107 (18) | 0.0048 (18) | −0.0012 (17) |
Br1—C27 | 1.903 (3) | C18—H18 | 0.9300 |
Br2—C9 | 1.911 (3) | C19—C20 | 1.391 (4) |
C1—C6 | 1.389 (5) | C19—C24 | 1.397 (5) |
C1—C2 | 1.395 (5) | C19—C25 | 1.491 (4) |
C1—C7 | 1.480 (5) | C20—C21 | 1.388 (5) |
C2—C3 | 1.381 (5) | C20—H20 | 0.9300 |
C2—H2 | 0.9300 | C21—C22 | 1.372 (5) |
C3—C4 | 1.371 (6) | C21—H21 | 0.9300 |
C3—H3 | 0.9300 | C22—C23 | 1.377 (5) |
C4—C5 | 1.370 (6) | C22—H22 | 0.9300 |
C4—H4 | 0.9300 | C23—C24 | 1.385 (5) |
C5—C6 | 1.391 (5) | C23—H23 | 0.9300 |
C5—H5 | 0.9300 | C24—H24 | 0.9300 |
C6—H6 | 0.9300 | C25—C30 | 1.387 (4) |
C7—C12 | 1.402 (4) | C25—C26 | 1.396 (4) |
C7—C8 | 1.396 (4) | C26—C27 | 1.371 (4) |
C8—C9 | 1.382 (5) | C26—H26 | 0.9300 |
C8—H8 | 0.9300 | C27—C28 | 1.386 (4) |
C9—C10 | 1.370 (5) | C28—C29 | 1.397 (4) |
C10—C11 | 1.403 (4) | C28—H28 | 0.9300 |
C10—H10 | 0.9300 | C29—C30 | 1.395 (4) |
C11—C12 | 1.385 (4) | C29—C31 | 1.484 (4) |
C11—C13 | 1.486 (4) | C30—H30 | 0.9300 |
C12—H12 | 0.9300 | C31—C32 | 1.394 (5) |
C13—C14 | 1.391 (4) | C31—C36 | 1.392 (5) |
C13—C18 | 1.392 (5) | C32—C33 | 1.370 (5) |
C14—C15 | 1.391 (5) | C32—H32 | 0.9300 |
C14—H14 | 0.9300 | C33—C34 | 1.378 (6) |
C15—C16 | 1.376 (5) | C33—H33 | 0.9300 |
C15—H15 | 0.9300 | C34—C35 | 1.371 (6) |
C16—C17 | 1.375 (5) | C34—H34 | 0.9300 |
C16—H16 | 0.9300 | C35—C36 | 1.375 (5) |
C17—C18 | 1.389 (5) | C35—H35 | 0.9300 |
C17—H17 | 0.9300 | C36—H36 | 0.9300 |
C6—C1—C2 | 117.6 (3) | C20—C19—C24 | 117.8 (3) |
C6—C1—C7 | 121.2 (3) | C20—C19—C25 | 120.9 (3) |
C2—C1—C7 | 121.2 (3) | C24—C19—C25 | 121.3 (3) |
C3—C2—C1 | 121.0 (4) | C21—C20—C19 | 121.1 (3) |
C3—C2—H2 | 119.5 | C21—C20—H20 | 119.5 |
C1—C2—H2 | 119.5 | C19—C20—H20 | 119.5 |
C4—C3—C2 | 120.4 (4) | C22—C21—C20 | 119.9 (3) |
C4—C3—H3 | 119.8 | C22—C21—H21 | 120.0 |
C2—C3—H3 | 119.8 | C20—C21—H21 | 120.0 |
C5—C4—C3 | 119.8 (4) | C21—C22—C23 | 120.3 (3) |
C5—C4—H4 | 120.1 | C21—C22—H22 | 119.9 |
C3—C4—H4 | 120.1 | C23—C22—H22 | 119.9 |
C4—C5—C6 | 120.1 (4) | C22—C23—C24 | 119.9 (3) |
C4—C5—H5 | 119.9 | C22—C23—H23 | 120.0 |
C6—C5—H5 | 119.9 | C24—C23—H23 | 120.0 |
C1—C6—C5 | 121.0 (4) | C23—C24—C19 | 121.0 (3) |
C1—C6—H6 | 119.5 | C23—C24—H24 | 119.5 |
C5—C6—H6 | 119.5 | C19—C24—H24 | 119.5 |
C12—C7—C8 | 118.7 (3) | C30—C25—C26 | 118.3 (3) |
C12—C7—C1 | 121.1 (3) | C30—C25—C19 | 121.0 (3) |
C8—C7—C1 | 120.2 (3) | C26—C25—C19 | 120.7 (3) |
C9—C8—C7 | 118.3 (3) | C27—C26—C25 | 119.8 (3) |
C9—C8—H8 | 120.8 | C27—C26—H26 | 120.1 |
C7—C8—H8 | 120.8 | C25—C26—H26 | 120.1 |
C10—C9—C8 | 123.2 (3) | C26—C27—C28 | 122.2 (3) |
C10—C9—Br2 | 118.5 (3) | C26—C27—Br1 | 118.9 (2) |
C8—C9—Br2 | 118.2 (2) | C28—C27—Br1 | 118.8 (2) |
C9—C10—C11 | 119.3 (3) | C27—C28—C29 | 119.0 (3) |
C9—C10—H10 | 120.3 | C27—C28—H28 | 120.5 |
C11—C10—H10 | 120.3 | C29—C28—H28 | 120.5 |
C12—C11—C10 | 118.1 (3) | C30—C29—C28 | 118.5 (3) |
C12—C11—C13 | 121.6 (3) | C30—C29—C31 | 121.5 (3) |
C10—C11—C13 | 120.3 (3) | C28—C29—C31 | 119.9 (3) |
C11—C12—C7 | 122.4 (3) | C25—C30—C29 | 122.2 (3) |
C11—C12—H12 | 118.8 | C25—C30—H30 | 118.9 |
C7—C12—H12 | 118.8 | C29—C30—H30 | 118.9 |
C14—C13—C18 | 117.6 (3) | C32—C31—C36 | 117.3 (3) |
C14—C13—C11 | 121.3 (3) | C32—C31—C29 | 121.7 (3) |
C18—C13—C11 | 121.1 (3) | C36—C31—C29 | 121.0 (3) |
C13—C14—C15 | 121.1 (3) | C33—C32—C31 | 121.4 (4) |
C13—C14—H14 | 119.4 | C33—C32—H32 | 119.3 |
C15—C14—H14 | 119.4 | C31—C32—H32 | 119.3 |
C16—C15—C14 | 120.1 (3) | C32—C33—C34 | 120.1 (4) |
C16—C15—H15 | 119.9 | C32—C33—H33 | 119.9 |
C14—C15—H15 | 119.9 | C34—C33—H33 | 119.9 |
C17—C16—C15 | 119.7 (3) | C35—C34—C33 | 119.7 (4) |
C17—C16—H16 | 120.1 | C35—C34—H34 | 120.2 |
C15—C16—H16 | 120.1 | C33—C34—H34 | 120.2 |
C16—C17—C18 | 120.2 (3) | C34—C35—C36 | 120.3 (4) |
C16—C17—H17 | 119.9 | C34—C35—H35 | 119.9 |
C18—C17—H17 | 119.9 | C36—C35—H35 | 119.9 |
C17—C18—C13 | 121.1 (3) | C35—C36—C31 | 121.2 (4) |
C17—C18—H18 | 119.4 | C35—C36—H36 | 119.4 |
C13—C18—H18 | 119.4 | C31—C36—H36 | 119.4 |
C6—C1—C2—C3 | −1.1 (5) | C24—C19—C20—C21 | −0.2 (5) |
C7—C1—C2—C3 | 179.5 (3) | C25—C19—C20—C21 | 180.0 (3) |
C1—C2—C3—C4 | 0.0 (6) | C19—C20—C21—C22 | 0.3 (5) |
C2—C3—C4—C5 | 0.4 (6) | C20—C21—C22—C23 | 0.0 (5) |
C3—C4—C5—C6 | 0.2 (6) | C21—C22—C23—C24 | −0.4 (5) |
C2—C1—C6—C5 | 1.7 (5) | C22—C23—C24—C19 | 0.4 (5) |
C7—C1—C6—C5 | −178.9 (4) | C20—C19—C24—C23 | −0.2 (5) |
C4—C5—C6—C1 | −1.3 (6) | C25—C19—C24—C23 | 179.6 (3) |
C6—C1—C7—C12 | 40.4 (5) | C20—C19—C25—C30 | −30.1 (5) |
C2—C1—C7—C12 | −140.2 (3) | C24—C19—C25—C30 | 150.1 (3) |
C6—C1—C7—C8 | −139.7 (4) | C20—C19—C25—C26 | 150.2 (3) |
C2—C1—C7—C8 | 39.8 (5) | C24—C19—C25—C26 | −29.6 (5) |
C12—C7—C8—C9 | 0.1 (5) | C30—C25—C26—C27 | 1.6 (5) |
C1—C7—C8—C9 | −179.8 (3) | C19—C25—C26—C27 | −178.7 (3) |
C7—C8—C9—C10 | 0.2 (5) | C25—C26—C27—C28 | −1.2 (6) |
C7—C8—C9—Br2 | −176.9 (3) | C25—C26—C27—Br1 | 176.9 (3) |
C8—C9—C10—C11 | −0.2 (5) | C26—C27—C28—C29 | 0.3 (6) |
Br2—C9—C10—C11 | 176.9 (2) | Br1—C27—C28—C29 | −177.8 (3) |
C9—C10—C11—C12 | −0.1 (5) | C27—C28—C29—C30 | 0.2 (5) |
C9—C10—C11—C13 | −179.9 (3) | C27—C28—C29—C31 | 178.2 (4) |
C10—C11—C12—C7 | 0.5 (5) | C26—C25—C30—C29 | −1.1 (5) |
C13—C11—C12—C7 | −179.7 (3) | C19—C25—C30—C29 | 179.1 (3) |
C8—C7—C12—C11 | −0.4 (5) | C28—C29—C30—C25 | 0.3 (6) |
C1—C7—C12—C11 | 179.5 (3) | C31—C29—C30—C25 | −177.7 (3) |
C12—C11—C13—C14 | 27.4 (5) | C30—C29—C31—C32 | 37.1 (5) |
C10—C11—C13—C14 | −152.8 (3) | C28—C29—C31—C32 | −140.9 (4) |
C12—C11—C13—C18 | −153.2 (3) | C30—C29—C31—C36 | −143.4 (4) |
C10—C11—C13—C18 | 26.6 (5) | C28—C29—C31—C36 | 38.6 (5) |
C18—C13—C14—C15 | −0.2 (5) | C36—C31—C32—C33 | −1.7 (6) |
C11—C13—C14—C15 | 179.2 (3) | C29—C31—C32—C33 | 177.8 (4) |
C13—C14—C15—C16 | −0.8 (5) | C31—C32—C33—C34 | 1.4 (6) |
C14—C15—C16—C17 | 1.5 (5) | C32—C33—C34—C35 | −0.5 (6) |
C15—C16—C17—C18 | −1.0 (5) | C33—C34—C35—C36 | −0.2 (6) |
C16—C17—C18—C13 | 0.0 (5) | C34—C35—C36—C31 | −0.2 (6) |
C14—C13—C18—C17 | 0.6 (5) | C32—C31—C36—C35 | 1.1 (5) |
C11—C13—C18—C17 | −178.7 (3) | C29—C31—C36—C35 | −178.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···Cg1i | 0.93 | 2.82 | 3.601 (4) | 142 |
C18—H18···Cg6ii | 0.93 | 2.84 | 3.682 (4) | 152 |
C20—H20···Cg1iii | 0.93 | 2.92 | 3.603 (4) | 132 |
Symmetry codes: (i) x, y−1, z; (ii) −x, y+1/2, −z; (iii) −x+1, y+1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C18H13Br |
Mr | 309.19 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 294 |
a, b, c (Å) | 11.0782 (12), 7.7495 (8), 16.7782 (17) |
β (°) | 107.441 (1) |
V (Å3) | 1374.2 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.97 |
Crystal size (mm) | 0.41 × 0.13 × 0.09 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.375, 0.776 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7808, 4775, 4138 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.076, 1.00 |
No. of reflections | 4775 |
No. of parameters | 343 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.31 |
Absolute structure | Flack (1983), 2006 Friedel pairs |
Absolute structure parameter | 0.007 (7) |
Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···Cg1i | 0.93 | 2.82 | 3.601 (4) | 142 |
C18—H18···Cg6ii | 0.93 | 2.84 | 3.682 (4) | 152 |
C20—H20···Cg1iii | 0.93 | 2.92 | 3.603 (4) | 132 |
Symmetry codes: (i) x, y−1, z; (ii) −x, y+1/2, −z; (iii) −x+1, y+1/2, −z. |
Acknowledgements
This work was supported by the National Natural Science Foundation of China (No. 20872057).
References
Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Kim, Y. H., Shin, D. C., Kim, S. H., Ko, C. H., Yu, H. S., Chae, Y. S. & Kwon, S. K. (2001). Adv. Mater. 13, 1690–1693. Web of Science CrossRef CAS Google Scholar
Niu, Y. H., Chen, B. Q., Kim, T. D., Liu, M. S. & Jen, A. K. Y. (2004). Appl. Phys. Lett. 85, 5433–5435. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suezawa, H., Ishihara, S., Umezawa, Y., Tsuboyama, S. & Nishio, M. (2004). Eur. J. Org. Chem. pp. 4816–4822. CrossRef Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
3,5-Diphenylbenzene is a good substituent for organic light-emitting materials. The thermal properties, photophysical properties and film formation properties of organic light-emitting materials can be improved efficiently by introducing 3,5-diphenylbenzene group (Niu, et al., 2004). The title compound, 3, 5-Diphenyl-1-bromobenzene, is generally used as the precursor to produce the 3, 5-diphenylbenzene group by Suzuki coupling reaction. The crystal structure of the title compound has not been reported to the best of our knowledge.
A view of the two independent molecules of the title compound shows distinct rotations of phenyl rings (Fig.1). The dihedral angles between adjacent benzene rings are 26.85 (2)° and 39.99 (2)° in one molecule, 29.90 (2)° and 38.01 (2)° in the other molecule. The C—Br bond lengths in the two crystallographically independent molecules are 1.903 (3) Å and 1.911 (3) Å, and the C—C bond lengths between benzene rings are 1.480 (5) Å (C1—C7), 1.486 (4) Å (C11—C13), 1.491 (4) Å (C19—C25), and 1.484 (4) Å (C29—C31), respectively. Three types of weak intermolecular C—H···π interactions exist in the crystal structure (Table 1, Cg1 and Cg6 are the centroids of the benzene rings C19 - C24 and C13 - C18). A detailed discussion for C—H···π interactions and geometries was presented by Suezawa et al. (2004).