In the title compound, C(20)H(16)Br(2), the terminal phenyl groups are twisted away from the central ring by approximately 55 and -125 degrees (average of four dihedral angles each), respectively. The crystal structure is stabilized by a combination of interMolecular and intraMolecular interactions including interMolecular pi-pi stacking interactions [C atoms of closest contact = 3.423 ( 5) angstrom]

Briggs, Jonathan B

Jazdzyk, Mikael D.

Miller, Glen P.

English

PubMed

UNH Scholars' Repository

University of New HampshireUniversity of New Hampshire Scholars' RepositoryChemistry Scholarship Chemistry1-20102,3-Bis(bromomethyl)-1,4-diphenylbenzeneJonathan B. BriggsUniversity of New Hampshire, Jon.Briggs@unh.eduMikael D. JazdzykUniversity of New HampshireGlen P. MillerUniversity of New Hampshire, Glen.Miller@unh.eduFollow this and additional works at: https://scholars.unh.edu/chemistry_facpubPart of the Organic Chemistry CommonsThis Article is brought to you for free and open access by the Chemistry at University of New Hampshire Scholars' Repository. It has been accepted forinclusion in Chemistry Scholarship by an authorized administrator of University of New Hampshire Scholars' Repository. For more information, pleasecontact nicole.hentz@unh.edu.Recommended CitationBriggs, Jonathan B.; Jazdzyk, Mikael D.; and Miller, Glen P., "2,3-Bis(bromomethyl)-1,4-diphenylbenzene" (2010). ActaCrystallographica Section E Structure Reports Online. 3.https://scholars.unh.edu/chemistry_facpub/32,3-Bis(bromomethyl)-1,4-diphenyl-benzeneJonathan B. Briggs, Mikae¨l D. Jazdzyk and Glen P. Miller*Department of Chemistry and Materials Science Program, University of NewHampshire, Durham, NH 03824-3598, USACorrespondence e-mail: glen.miller@unh.eduReceived 28 September 2009; accepted 25 November 2009Key indicators: single-crystal X-ray study; T = 296 K; mean (C–C) = 0.005 A˚;R factor = 0.031; wR factor = 0.117; data-to-parameter ratio = 14.8.In the title compound, C20H16Br2, the terminal phenyl groupsare twisted away from the central ring by approximately 55and 125 (average of four dihedral angles each), respec-tively. The crystal structure is stabilized by a combination ofintermolecular and intramolecular interactions includingintermolecular – stacking interactions [C atoms of closestcontact = 3.423 (5) A˚].Related literatureFor the synthesis of terphenyls, see: Ames (1958). For thesynthesis and applications of the title compound, see: Bredowet al. (1970); Geng et al. (2002); Martin & Segura (1999). Forrelated structures, see: Baudour et al. (1986); Baker et al.(1993).ExperimentalCrystal dataC20H16Br2Mr = 416.15Monoclinic, P21=ca = 8.8589 (10) A˚b = 11.5859 (13) A˚c = 16.655 (2) A˚ = 102.393 (4)V = 1669.6 (3) A˚3Z = 4Mo K radiation = 4.85 mm1T = 296 K0.50  0.50  0.05 mmData collectionBruker SMART X2S diffractometerAbsorption correction: multi-scan(SADABS; Bruker, 2007)Tmin = 0.195, Tmax = 0.79410674 measured reflections2955 independent reflections2395 reflections with I > 2(I)Rint = 0.033RefinementR[F 2 > 2(F 2)] = 0.031wR(F 2) = 0.117S = 0.902955 reflections199 parametersH-atom parameters constrainedmax = 0.48 e A˚3min = 0.84 e A˚3Table 1Hydrogen-bond geometry (A˚, ).D—H  A D—H H  A D  A D—H  AC12—H12  Br19 0.93 2.93 3.644 (4) 134C20—H20A  Br19 0.97 2.80 3.563 (4) 136C14—H14  Br20 0.93 2.96 3.704 (4) 139C19—H19A  Br20 0.97 2.80 3.552 (4) 135C19—H19B  Br20i 0.97 2.98 3.632 (4) 126Symmetry code: (i) x þ 1; y 12;zþ 12.Data collection: GIS (Bruker, 2007); cell refinement: SAINT(Bruker, 2007); data reduction: SAINT; program(s) used to solvestructure: SHELXS97 (Sheldrick, 2008); program(s) used to refinestructure: SHELXL97 (Sheldrick, 2008); molecular graphics:SHELXTL (Sheldrick, 2008); software used to prepare material forpublication: SHELXTL.The authors thank the National Science Foundation forsupport of this work through the EPSCoR Research Infra-structure Improvement program (NSF 0432060) and theCenter for High-rate Nanomanufacturing (NSF EEC-0425826).Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: FL2275).ReferencesAmes, G. R. (1958). Chem. Rev. 58, 895–923.Baker, K. N., Fratini, A. V., Resch, T., Knachel, H. C., Adams, W. W., Socci, E.P. & Farmer, B. L. (1993). Polymer, 34, 1571–1587.Baudour, J. L., Toupet, L., De´lugeard, Y. & Ghe´mid, S. (1986). Acta Cryst. C42,1211–1217.Bredow, K. V, Jaeschke, A., Schmid, H. G., Friebolin, H. & Kabuss, S. (1970).Org. Magn. Reson. 2, 543–555.Bruker (2007). GIS, SADABS and SAINT. Bruker AXS Inc., Madison,Wisconsin, USA.Geng, Y., Katsis, D., Culligan, S. W., Ou, J. J., Chen, S. H. & Rothberg, L. J.(2002). Chem. Mater. 14, 463–470.Martin, N. & Segura, J. L. (1999). Chem. Rev. 99, 3199–3246.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.organic compoundso12 Briggs et al. doi:10.1107/S1600536809050764 Acta Cryst. (2010). E66, o12Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368supplementary materialssupplementary materialssup-1Acta Cryst. (2010). E66, o12    [ doi:10.1107/S1600536809050764 ]2,3-Bis(bromomethyl)-1,4-diphenylbenzeneJ. B. Briggs, M. D. Jazdzyk and G. P. MillerCommentFor a review on the synthesis of substituted terphenyls see Ames (1958). For the synthesis of the title compound, see Bredowet al. (1970). The title compound has been utilized as a reagent in the synthesis of spiro-configured terfluorenes (Geng et al.,2002) and is a potentially useful precursor to an o-quinodimethane derivative (Martin & Segura, 1999). For related crystalstructures, see Baudour et al. (1986); Baker et al. (1993).We define the three rings of the terphenyl moiety as α, β and γ (Figure 1). Thus, terminal ring α contains C7 – C12,central ring β contains C1 – C6, and terminal ring γ contains C13 – C18. The rotations of ring α and ring γ relative to centralring β are approximately 55 ° and -125 °, respectively.The rotations of ring α and ring γ are influenced by nearly equivalent sets of intramolecular C–H···π and C–H···Brinteractions (Tables 1–2) as illustrated in Figure 2. Each γ ring also engages in a stabilizing, intermolecular π–π stackinginteraction (C14···C16, 3.423 (5) Å) with another γ ring, as illustrated in Figure 3. The spacing between π–π stacking γrings is nearly identical to the 3.435 Å interlayer spacing in graphite suggesting a relatively strong π–π stacking interaction.Likewise, interacting pairs of γ rings lie in near perfect parallel orientations with respect to each other (Figure 3).There are 3 intermolecular and 4 intramolecular interactions involving Br atoms (Table 2). The intermolecular interac-tions consist of one significant Br–C interaction (Br19···C6, 3.470 (3) Å), one significant Br–H interaction (Br20···H19B,2.9788 (5) Å), and one relatively weak Br–Br interaction (Br19···Br20, 3.7743 (7) Å). With regards to intramolecular inter-actions involving bromine, each bromine atom (i.e., Br19 and Br20) interacts with one methylene hydrogen (Br19···H20A,2.7993 (5) Å; Br20···H19A, 2.7965 (6) Å) and one aryl hydrogen (Br19···H12, 2.9348 (5) Å; Br20···H14, 2.9559 (6) Å). Bothcan be viewed as halogen variations of traditional H-bonding, the first set shorter and stronger presumably due to the greateracidity associated with a proton on a benzylic bromide as compared to an aryl proton. An MM2 calculated structure for thetitle compound (not parameterized for Br···H interactions) indicates much longer Br···H distances (Br19,20···H19A,20 A,3.14 Å; Br19,20···H12,14 3.79 Å) suggesting that Br···H-bonding in the crystal is both real and stabilizing.Several intermolecular C–H···π interactions are also observed in the crystal structure (Table 1) but all have H···π distancesgreater than 3 Å and appear to be relatively weak.ExperimentalThe title compound was prepared via the published method (Bredow et al., 1970) as illustrated in Figure 4. 1H NMR(400 MHz, CDCl3) δ 4.72 (s, 4H), 7.27 (s, 2H), 7.40–7.54 (m, 10H); 13C NMR (100 MHz, CDCl3) δ 29.2 (CH2), 128.0(CH), 128.6 (CH), 129.2 (CH), 131.0 (CH), 135.1 (C), 140.4 (C), 143.7 (C). An X-ray grade crystal was grown from slowevaporation of a saturated chloroform solution.supplementary materialssup-2FiguresFig. 1. The molecular structure showing the crystallographic labeling scheme and displace-ment ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitraryradii.Fig. 2. Perspective view of the title compound showing five nearly equivalent sets of in-tramolecular interactions involving the α and γ rings (see Comment section and Tables 1–2).Fig. 3. Perspective view of long range packing in the crystal structure including relativelyweak intermolecular Br—Br and relatively strong intermolecular π-π stacking interactions.Fig. 4. Synthesis of the title compound, 2,3-bis(bromomethyl)-1,4-diphenylbenzene.2,3-Bis(bromomethyl)-1,4-diphenylbenzeneCrystal dataC20H16Br2 F(000) = 824Mr = 416.15 Dx = 1.656 Mg m−3Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 ÅHall symbol: -P 2ybc Cell parameters from 4281 reflectionsa = 8.8589 (10) Å θ = 2.4–24.7°b = 11.5859 (13) Å µ = 4.85 mm−1c = 16.655 (2) Å T = 296 Kβ = 102.393 (4)° Plate, colourlessV = 1669.6 (3) Å3 0.50 × 0.50 × 0.05 mmZ = 4Data collectionBruker SMART X2Sdiffractometer 2955 independent reflectionsRadiation source: micro-focus sealed tube 2395 reflections with I > 2σ(I)doubly curved silicon crystal Rint = 0.033ω scans θmax = 25.1°, θmin = 2.2°Absorption correction: multi-scan(SADABS; Bruker, 2007) h = −9→10Tmin = 0.195, Tmax = 0.794 k = −12→13supplementary materialssup-310674 measured reflections l = −19→18RefinementRefinement on F2Primary atom site location: structure-invariant directmethodsLeast-squares matrix: full Secondary atom site location: difference Fourier mapR[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouringsiteswR(F2) = 0.117 H-atom parameters constrainedS = 0.90w = 1/[σ2(Fo2) + (0.1P)2]where P = (Fo2 + 2Fc2)/32955 reflections (Δ/σ)max < 0.001199 parameters Δρmax = 0.48 e Å−30 restraints Δρmin = −0.84 e Å−3Special detailsGeometry. 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 mat-rix. 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; correlationsbetween e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment ofcell 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, convention-al 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 largeas 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)x y z Uiso*/UeqC1 0.7911 (4) 0.0211 (3) 0.11822 (18) 0.0261 (7)C2 0.6744 (3) 0.1014 (3) 0.12258 (18) 0.0251 (7)C3 0.6754 (3) 0.2110 (3) 0.08567 (18) 0.0251 (7)C4 0.7904 (4) 0.2404 (3) 0.04258 (19) 0.0269 (7)C5 0.9077 (4) 0.1602 (3) 0.04184 (19) 0.0296 (7)H5 0.9868 0.1787 0.0153 0.035*C6 0.9090 (4) 0.0545 (3) 0.0793 (2) 0.0292 (7)H6 0.9903 0.0039 0.0788 0.035*C7 0.7963 (4) −0.0981 (3) 0.15312 (19) 0.0298 (7)C8 0.9294 (4) −0.1362 (3) 0.2071 (2) 0.0408 (9)H8 1.0137 −0.0869 0.2219 0.049*C9 0.9371 (5) −0.2470 (4) 0.2389 (3) 0.0522 (11)H9 1.0268 −0.2716 0.2747 0.063*C10 0.8145 (5) −0.3204 (3) 0.2184 (3) 0.0533 (11)H10 0.8195 −0.3940 0.2410 0.064*C11 0.6828 (5) −0.2845 (3) 0.1635 (3) 0.0530 (11)H11 0.5999 −0.3348 0.1483 0.064*supplementary materialssup-4C12 0.6736 (4) −0.1744 (3) 0.1314 (2) 0.0419 (9)H12 0.5843 −0.1511 0.0947 0.050*C13 0.7925 (4) 0.3495 (3) −0.0039 (2) 0.0312 (7)C14 0.7961 (4) 0.4578 (3) 0.0321 (2) 0.0380 (8)H14 0.7928 0.4636 0.0874 0.046*C15 0.8044 (5) 0.5578 (4) −0.0128 (3) 0.0512 (11)H15 0.8063 0.6294 0.0125 0.061*C16 0.8098 (5) 0.5512 (4) −0.0940 (3) 0.0532 (11)H16 0.8150 0.6181 −0.1241 0.064*C17 0.8075 (5) 0.4442 (4) −0.1311 (3) 0.0562 (12)H17 0.8118 0.4392 −0.1863 0.067*C18 0.7989 (4) 0.3441 (4) −0.0863 (2) 0.0429 (9)H18 0.7974 0.2726 −0.1119 0.051*C19 0.5527 (4) 0.0732 (3) 0.16939 (19) 0.0300 (7)H19A 0.5369 0.1395 0.2022 0.036*H19B 0.5883 0.0097 0.2066 0.036*C20 0.5528 (4) 0.2970 (3) 0.0926 (2) 0.0333 (8)H20A 0.4540 0.2581 0.0866 0.040*H20B 0.5441 0.3538 0.0491 0.040*Br19 0.35394 (4) 0.03039 (4) 0.09650 (2) 0.04810 (18)Br20 0.60479 (5) 0.37511 (4) 0.20073 (3) 0.05089 (18)Atomic displacement parameters (Å2)U11 U22 U33 U12 U13 U23C1 0.0308 (17) 0.0256 (18) 0.0219 (15) −0.0022 (13) 0.0056 (13) −0.0038 (12)C2 0.0217 (15) 0.0319 (19) 0.0210 (14) −0.0010 (13) 0.0028 (12) −0.0052 (13)C3 0.0240 (15) 0.0283 (18) 0.0218 (15) 0.0003 (13) 0.0027 (12) −0.0034 (12)C4 0.0296 (17) 0.0271 (18) 0.0241 (15) −0.0016 (13) 0.0057 (12) −0.0037 (13)C5 0.0287 (16) 0.0316 (19) 0.0311 (17) −0.0014 (14) 0.0126 (13) −0.0036 (14)C6 0.0271 (16) 0.0308 (18) 0.0319 (17) 0.0046 (13) 0.0110 (13) −0.0033 (14)C7 0.0372 (18) 0.0271 (18) 0.0269 (16) 0.0037 (14) 0.0111 (14) −0.0048 (13)C8 0.046 (2) 0.037 (2) 0.038 (2) 0.0043 (17) 0.0047 (16) 0.0014 (16)C9 0.069 (3) 0.041 (2) 0.044 (2) 0.014 (2) 0.0068 (19) 0.0061 (18)C10 0.081 (3) 0.027 (2) 0.056 (3) 0.010 (2) 0.025 (2) 0.0103 (19)C11 0.064 (3) 0.029 (2) 0.070 (3) −0.0084 (19) 0.023 (2) −0.0034 (19)C12 0.044 (2) 0.034 (2) 0.047 (2) −0.0011 (17) 0.0089 (17) 0.0009 (17)C13 0.0262 (16) 0.038 (2) 0.0300 (17) 0.0017 (14) 0.0061 (13) 0.0065 (14)C14 0.040 (2) 0.033 (2) 0.044 (2) 0.0044 (15) 0.0148 (16) 0.0038 (16)C15 0.046 (2) 0.036 (2) 0.076 (3) 0.0051 (18) 0.023 (2) 0.011 (2)C16 0.043 (2) 0.054 (3) 0.064 (3) 0.0082 (19) 0.015 (2) 0.030 (2)C17 0.051 (3) 0.080 (4) 0.036 (2) −0.001 (2) 0.0060 (18) 0.025 (2)C18 0.047 (2) 0.048 (2) 0.0323 (19) −0.0016 (18) 0.0066 (16) 0.0047 (17)C19 0.0283 (16) 0.0346 (19) 0.0274 (16) −0.0030 (14) 0.0068 (13) −0.0023 (14)C20 0.0291 (17) 0.033 (2) 0.0388 (18) 0.0063 (14) 0.0089 (14) 0.0034 (15)Br19 0.0284 (2) 0.0633 (3) 0.0510 (3) −0.00986 (16) 0.00496 (17) −0.00181 (18)Br20 0.0586 (3) 0.0429 (3) 0.0588 (3) 0.00343 (18) 0.0298 (2) −0.01598 (18)supplementary materialssup-5Geometric parameters (Å, °)C1—C6 1.397 (5) C11—C12 1.378 (5)C1—C2 1.403 (5) C11—H11 0.9300C1—C7 1.496 (5) C12—H12 0.9300C2—C3 1.412 (4) C13—C14 1.388 (5)C2—C19 1.496 (5) C13—C18 1.387 (5)C3—C4 1.408 (4) C14—C15 1.389 (5)C3—C20 1.497 (4) C14—H14 0.9300C4—C5 1.396 (5) C15—C16 1.366 (6)C4—C13 1.485 (5) C15—H15 0.9300C5—C6 1.373 (5) C16—C17 1.384 (6)C5—H5 0.9300 C16—H16 0.9300C6—H6 0.9300 C17—C18 1.390 (6)C7—C8 1.392 (5) C17—H17 0.9300C7—C12 1.387 (5) C18—H18 0.9300C8—C9 1.385 (5) C19—Br19 1.976 (3)C8—H8 0.9300 C19—H19A 0.9700C9—C10 1.364 (6) C19—H19B 0.9700C9—H9 0.9300 C20—Br20 1.979 (3)C10—C11 1.382 (6) C20—H20A 0.9700C10—H10 0.9300 C20—H20B 0.9700C6—C1—C2 118.2 (3) C7—C12—C11 120.7 (4)C6—C1—C7 118.2 (3) C7—C12—H12 119.7C2—C1—C7 123.6 (3) C11—C12—H12 119.7C1—C2—C3 120.0 (3) C14—C13—C18 117.8 (3)C1—C2—C19 120.2 (3) C14—C13—C4 123.1 (3)C3—C2—C19 119.7 (3) C18—C13—C4 119.0 (3)C2—C3—C4 120.8 (3) C13—C14—C15 121.3 (4)C2—C3—C20 119.5 (3) C13—C14—H14 119.4C4—C3—C20 119.7 (3) C15—C14—H14 119.4C3—C4—C5 117.6 (3) C16—C15—C14 120.3 (4)C3—C4—C13 124.3 (3) C16—C15—H15 119.9C5—C4—C13 118.0 (3) C14—C15—H15 119.9C6—C5—C4 121.6 (3) C15—C16—C17 119.5 (4)C6—C5—H5 119.2 C15—C16—H16 120.2C4—C5—H5 119.2 C17—C16—H16 120.2C5—C6—C1 121.6 (3) C18—C17—C16 120.3 (4)C5—C6—H6 119.2 C18—C17—H17 119.8C1—C6—H6 119.2 C16—C17—H17 119.8C8—C7—C12 118.3 (3) C17—C18—C13 120.8 (4)C8—C7—C1 119.6 (3) C17—C18—H18 119.6C12—C7—C1 122.0 (3) C13—C18—H18 119.6C7—C8—C9 120.4 (4) C2—C19—Br19 112.4 (2)C7—C8—H8 119.8 C2—C19—H19A 109.1C9—C8—H8 119.8 Br19—C19—H19A 109.1C10—C9—C8 120.7 (4) C2—C19—H19B 109.1C10—C9—H9 119.6 Br19—C19—H19B 109.1supplementary materialssup-6C8—C9—H9 119.6 H19A—C19—H19B 107.8C9—C10—C11 119.4 (4) C3—C20—Br20 110.1 (2)C9—C10—H10 120.3 C3—C20—H20A 109.6C11—C10—H10 120.3 Br20—C20—H20A 109.6C10—C11—C12 120.4 (4) C3—C20—H20B 109.6C10—C11—H11 119.8 Br20—C20—H20B 109.6C12—C11—H11 119.8 H20A—C20—H20B 108.2C6—C1—C2—C3 2.2 (4) C7—C8—C9—C10 −0.3 (6)C7—C1—C2—C3 −178.0 (3) C8—C9—C10—C11 1.6 (6)C6—C1—C2—C19 −175.1 (3) C9—C10—C11—C12 −1.6 (6)C7—C1—C2—C19 4.8 (4) C8—C7—C12—C11 1.0 (5)C1—C2—C3—C4 1.5 (4) C1—C7—C12—C11 178.9 (3)C19—C2—C3—C4 178.8 (3) C10—C11—C12—C7 0.2 (6)C1—C2—C3—C20 −178.4 (3) C3—C4—C13—C14 58.9 (4)C19—C2—C3—C20 −1.1 (4) C5—C4—C13—C14 −122.9 (4)C2—C3—C4—C5 −3.6 (4) C3—C4—C13—C18 −124.3 (3)C20—C3—C4—C5 176.3 (3) C5—C4—C13—C18 53.9 (4)C2—C3—C4—C13 174.6 (3) C18—C13—C14—C15 0.5 (5)C20—C3—C4—C13 −5.5 (5) C4—C13—C14—C15 177.3 (3)C3—C4—C5—C6 2.1 (4) C13—C14—C15—C16 −0.2 (6)C13—C4—C5—C6 −176.2 (3) C14—C15—C16—C17 −0.2 (6)C4—C5—C6—C1 1.6 (5) C15—C16—C17—C18 0.4 (6)C2—C1—C6—C5 −3.7 (5) C16—C17—C18—C13 0.0 (6)C7—C1—C6—C5 176.4 (3) C14—C13—C18—C17 −0.4 (5)C6—C1—C7—C8 53.1 (4) C4—C13—C18—C17 −177.3 (3)C2—C1—C7—C8 −126.8 (3) C1—C2—C19—Br19 −103.0 (3)C6—C1—C7—C12 −124.8 (4) C3—C2—C19—Br19 79.7 (3)C2—C1—C7—C12 55.3 (4) C2—C3—C20—Br20 80.7 (3)C12—C7—C8—C9 −1.0 (5) C4—C3—C20—Br20 −99.2 (3)C1—C7—C8—C9 −179.0 (3)Hydrogen-bond geometry (Å, °)D—H···A D—H H···A D···A D—H···AC12—H12···Br19 0.93 2.93 3.644 (4) 134C20—H20A···Br19 0.97 2.80 3.563 (4) 136C14—H14···Br20 0.93 2.96 3.704 (4) 139C19—H19A···Br20 0.97 2.80 3.552 (4) 135C19—H19B···Br20i 0.97 2.98 3.632 (4) 126Symmetry codes: (i) −x+1, y−1/2, −z+1/2.Table 2C–H···π interaction geometry (Å, °)For atom numbers, see Figure 1 in supplementary materialsC–H···π C–H H···π C···π C–H···π Ring Involved* C5-H5···C18 0.93 2.846 (4) 3.023 (5) 91.9 (2) γ* C6-H6···C8 0.93 2.826 (4) 3.046 (5) 94.7 (2) α* C8-H8···C6 0.93 2.870 (3) 3.046 (5) 91.9 (2) αsupplementary materialssup-7* C18-H18···C5 0.93 2.852 (3) 3.023 (5) 91.5 (2) γ* C19-H19B···C7 0.97 2.540 (4) 2.987 (5) 108.0 (2) α* C19-H19B···C12 0.97 2.664 (4) 3.173 (5) 113.1 (2) α* C20-H20B···C13 0.97 2.541 (4) 2.988 (5) 108.1 (2) γ* C20-H20B···C14 0.97 2.605 (4) 3.172 (5) 117.6 (2) γ# C6-H6···C5 0.93 3.041 (4) 3.782 (5) 137.8 (2) β# C6-H6···C6 0.93 3.032 (4) 3.606 (5) 121.4 (2) β# C9-H9···C5 0.93 3.088 (3) 3.772 (6) 131.8 (3) α# C19-H19B···C17 0.97 3.018 (4) 3.600 (5) 119.8 (2) γ* indicates an intramolecular interaction; # indicates an intermolecular interactionsupplementary materialssup-8Fig. 1supplementary materialssup-9Fig. 2supplementary materialssup-10Fig. 3supplementary materialssup-11Fig. 4

2,3-Bis(bromomethyl)-1,4-diphenylbenzene

In the title compound, C20H16Br2, the terminal phenyl groups are twisted away from the central ring by approximately 55 and &amp;#8722;125&amp;#176; (average of four dihedral angles each), respectively. The crystal structure is stabilized by a combination of intermolecular and intramolecular interactions including intermolecular &amp;#960;&amp;#8211;&amp;#960; stacking interactions [C atoms of closest contact = 3.423&amp;#8197;(5)&amp;#8197;&amp;#197;]

Jonathan B. Briggs

Mika&amp

Glen P. Miller

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Acta Cryst. A64, 112–122. organic compounds o12

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) x y z Uiso*/Ueq

L.,De ´lugeard,

Synthesis of the title compound, 2,3-bis(bromomethyl)-1,4-diphenylbenzene. 2,3-Bis(bromomethyl)-1,4-diphenylbenzene Crystal data

http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=2980209

2,3-Bis(bromomethyl)-1,4-diphenylbenzene

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