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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2013 Jan 31;69(Pt 2):o307. doi: 10.1107/S1600536813002407

1-[3-(Naphthalen-1-yl)phen­yl]naphthal­ene1

Manorama Tummala a, Raj K Dhar a, Frank R Fronczek a,*, Steven F Watkins a
PMCID: PMC3569826  PMID: 23424572

Abstract

The title compound, C26H18, consists of a benzene ring with meta-substituted 1-naphthalene substituents, which are essentially planar (r.m.s. deviation = 0.039 and 0.027 Å). The conformation is mixed syn/anti, with equivalent torsion angles about the benzene–naphthalene bonds of 121.46 (11) and 51.58 (14)°.

Related literature  

For synthesis of the title compound, see: Woods et al. (1951 ▶). For similar structures, see Baker et al. (1990 ▶); Lin & Williams (1975 ▶); Bart (1968 ▶); Wolfenden et al. (2013 ▶). For MM2 calculations, see: CambridgeSoft (2010 ▶).graphic file with name e-69-0o307-scheme1.jpg

Experimental  

Crystal data  

  • C26H18

  • M r = 330.4

  • Triclinic, Inline graphic

  • a = 7.6272 (1) Å

  • b = 10.8453 (2) Å

  • c = 11.8454 (2) Å

  • α = 106.0798 (8)°

  • β = 96.2976 (8)°

  • γ = 108.4307 (9)°

  • V = 872.05 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 100 K

  • 0.28 × 0.22 × 0.15 mm

Data collection  

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.980, T max = 0.989

  • 11174 measured reflections

  • 6272 independent reflections

  • 4659 reflections with I > 2σ(I)

  • R int = 0.025

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.050

  • wR(F 2) = 0.138

  • S = 1.05

  • 6272 reflections

  • 289 parameters

  • Only H-atom coordinates refined

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.25 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Supplementary Material

Click here for additional data file. (19.3KB, cif)

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813002407/tk5189sup1.cif

e-69-0o307-sup1.cif (19.3KB, cif)
Click here for additional data file. (300.8KB, hkl)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002407/tk5189Isup2.hkl

e-69-0o307-Isup2.hkl (300.8KB, hkl)
Click here for additional data file. (6.6KB, cml)

Supplementary material file. DOI: 10.1107/S1600536813002407/tk5189Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The purchase of the diffractometer was made possible by grant No. LEQSF(1999–2000)-ESH-TR-13, administered by the Louisiana Board of Regents.

supplementary crystallographic information

Comment

Although the structures of p-oligophenyls have been well investigated (Baker et al., 1990, and references therein), there have been few reports of the conformational preferences of m-oligophenyls. Lin & Williams (1975) have reported the crystal structure of 1,3,5 triphenyl benzene, which serves as a model for m-polyphenyls. That structure has phenyl groups which are twisted about the benzene-benzene single bonds by torsion angles of +40.7, -37.2, and +36.1°. The crystal structure of one of the polymorphic forms of hexaphenyl benzene, reported by Bart (1968), also shows that the peripheral rings are twisted out of the central ring by about 25°. That molecule also exhibited out-of-plane distortion by bending of the exocyclic bonds. We have studied the structure of 1,3-bis(1-naphthyl)benzene for comparison of its conformation to the previous results.

Title compound I consists of a benzene ring with meta-substituted 1-naphthalenes. The benzene ring is planar (δr.m.s. = 0.007 Å), as are the two naphthalenes (δr.m.s. = 0.039 and 0.027 Å). MM2 calculations of isolated models (CambridgeSoft, 2010) reveal six conformers of I with approximately equal energies. They differ by positive or negative torsions C2—C1—C7—C8 (A1) and C2—C3—C17—C18 (A2) from the three paradigmatic conformers syn (C2v, A1, A2 = 0, 0°), anti (C2v, 180, 180°), and mixed (Cs, 180, 0°). The conformation of I is mixed (C1), with A1 = 121.46 (11)° and A2 = 51.58 (14)° (MM2 yields angles of 149 and 35° for the global minimum energy conformation).

Experimental

The crystal was prepared by refluxing di-(α-naphthyl)-cyclohexadiene with a Pd-charcoal mixture in p-cymene for 4–5 h. After filtration, the filtrate was steam distilled. The residue was extracted with ether and recrystallized from petroleum ether (Woods et al., 1951).

Refinement

All H atom positions were refined, but Uiso(H) was set to 1.2Ueq of the attached C atom. C–H distances fall within the range 0.973 (14) - 1.031 (15) Å.

Figures

Fig. 1.

Fig. 1.

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View of (I) (50% probability displacement ellipsoids)

Crystal data

C26H18 Z = 2
Mr = 330.4 F(000) = 348
Triclinic, P1 Dx = 1.258 Mg m−3
Hall symbol: -P 1 Melting point: 131.5(5) K
a = 7.6272 (1) Å Mo Kα radiation, λ = 0.71073 Å
b = 10.8453 (2) Å Cell parameters from 5528 reflections
c = 11.8454 (2) Å θ = 2.6–32.6°
α = 106.0798 (8)° µ = 0.07 mm−1
β = 96.2976 (8)° T = 100 K
γ = 108.4307 (9)° Prism, colourless
V = 872.05 (2) Å3 0.28 × 0.22 × 0.15 mm
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Data collection

Nonius KappaCCD diffractometer 6272 independent reflections
Radiation source: fine-focus sealed tube 4659 reflections with I > 2σ(I)
Graphite monochromator Rint = 0.025
Detector resolution: 9 pixels mm-1 θmax = 32.6°, θmin = 2.9°
φ and ω scans h = −11→11
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) k = −16→16
Tmin = 0.980, Tmax = 0.989 l = −17→17
11174 measured reflections
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Refinement

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)] = 0.050 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138 Only H-atom coordinates refined
S = 1.05 w = 1/[σ2(Fo2) + (0.0681P)2 + 0.1782P] where P = (Fo2 + 2Fc2)/3
6272 reflections (Δ/σ)max = 0.001
289 parameters Δρmax = 0.36 e Å−3
0 restraints Δρmin = −0.25 e Å−3
0 constraints
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Special details

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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
C1 0.82582 (14) 0.47008 (10) 0.81621 (9) 0.01484 (18)
C2 0.69555 (14) 0.50351 (10) 0.74916 (9) 0.01559 (18)
H2 0.5744 (18) 0.4321 (13) 0.7006 (12) 0.019*
C3 0.73683 (14) 0.63687 (10) 0.74479 (9) 0.01583 (18)
C4 0.91076 (15) 0.73893 (10) 0.81138 (9) 0.0186 (2)
H4 0.9414 (19) 0.8349 (14) 0.8107 (13) 0.022*
C5 1.04081 (15) 0.70701 (11) 0.87862 (9) 0.0192 (2)
H5 1.159 (2) 0.7783 (14) 0.9277 (13) 0.023*
C6 0.99993 (14) 0.57264 (10) 0.87979 (9) 0.01680 (19)
H6 1.0961 (19) 0.5510 (13) 0.9275 (12) 0.02*
C7 0.78015 (13) 0.32634 (10) 0.81691 (9) 0.01449 (18)
C8 0.89726 (15) 0.25621 (11) 0.77886 (10) 0.01835 (19)
H8 1.013 (2) 0.3032 (14) 0.7538 (13) 0.022*
C9 0.85267 (16) 0.11697 (11) 0.77163 (10) 0.0213 (2)
H9 0.939 (2) 0.0692 (15) 0.7408 (14) 0.026*
C10 0.69203 (16) 0.04918 (10) 0.80376 (10) 0.0200 (2)
H10 0.658 (2) −0.0494 (14) 0.7972 (13) 0.024*
C11 0.57133 (14) 0.11841 (10) 0.84745 (9) 0.01646 (19)
C12 0.40719 (16) 0.05083 (11) 0.88491 (10) 0.0216 (2)
H12 0.380 (2) −0.0479 (15) 0.8764 (13) 0.026*
C13 0.29543 (16) 0.11944 (12) 0.93179 (11) 0.0241 (2)
H13 0.183 (2) 0.0731 (15) 0.9603 (13) 0.029*
C14 0.34088 (16) 0.25987 (11) 0.94264 (10) 0.0217 (2)
H14 0.261 (2) 0.3096 (14) 0.9777 (13) 0.026*
C15 0.49569 (14) 0.32721 (10) 0.90471 (9) 0.01736 (19)
H15 0.5279 (19) 0.4277 (14) 0.9140 (13) 0.021*
C16 0.61575 (14) 0.25913 (9) 0.85565 (9) 0.01443 (18)
C17 0.59275 (14) 0.66850 (10) 0.67417 (9) 0.01692 (19)
C18 0.41114 (16) 0.63294 (12) 0.69381 (11) 0.0235 (2)
H18 0.378 (2) 0.5841 (15) 0.7523 (14) 0.028*
C19 0.27133 (17) 0.66524 (14) 0.63265 (12) 0.0287 (3)
H19 0.139 (2) 0.6350 (16) 0.6469 (14) 0.034*
C20 0.31553 (16) 0.73679 (13) 0.55434 (11) 0.0247 (2)
H20 0.216 (2) 0.7599 (15) 0.5088 (14) 0.03*
C21 0.49962 (15) 0.77453 (10) 0.53030 (9) 0.01804 (19)
C22 0.54657 (16) 0.84667 (11) 0.44775 (9) 0.0201 (2)
H22 0.4519 (19) 0.8779 (14) 0.4119 (13) 0.024*
C23 0.71984 (16) 0.87506 (11) 0.41886 (10) 0.0220 (2)
H23 0.751 (2) 0.9230 (14) 0.3557 (14) 0.026*
C24 0.85601 (16) 0.83222 (11) 0.47117 (10) 0.0215 (2)
H24 0.983 (2) 0.8506 (15) 0.4477 (13) 0.026*
C25 0.81667 (15) 0.76545 (11) 0.55395 (10) 0.01813 (19)
H25 0.9135 (19) 0.7354 (14) 0.5896 (13) 0.022*
C26 0.63915 (14) 0.73646 (10) 0.58754 (9) 0.01580 (18)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0164 (4) 0.0144 (4) 0.0145 (4) 0.0052 (3) 0.0046 (3) 0.0059 (3)
C2 0.0164 (4) 0.0139 (4) 0.0158 (4) 0.0050 (3) 0.0026 (3) 0.0049 (3)
C3 0.0181 (4) 0.0162 (4) 0.0149 (4) 0.0068 (3) 0.0050 (3) 0.0065 (3)
C4 0.0229 (5) 0.0152 (4) 0.0176 (5) 0.0046 (4) 0.0059 (4) 0.0072 (4)
C5 0.0195 (5) 0.0178 (4) 0.0166 (5) 0.0007 (4) 0.0028 (4) 0.0074 (4)
C6 0.0160 (4) 0.0188 (4) 0.0152 (4) 0.0041 (3) 0.0030 (3) 0.0079 (3)
C7 0.0153 (4) 0.0141 (4) 0.0137 (4) 0.0051 (3) 0.0016 (3) 0.0048 (3)
C8 0.0185 (5) 0.0197 (4) 0.0188 (5) 0.0089 (4) 0.0047 (4) 0.0068 (4)
C9 0.0251 (5) 0.0205 (5) 0.0217 (5) 0.0134 (4) 0.0046 (4) 0.0062 (4)
C10 0.0262 (5) 0.0152 (4) 0.0192 (5) 0.0098 (4) 0.0019 (4) 0.0054 (4)
C11 0.0197 (5) 0.0131 (4) 0.0150 (4) 0.0044 (3) 0.0010 (3) 0.0050 (3)
C12 0.0237 (5) 0.0169 (4) 0.0217 (5) 0.0023 (4) 0.0036 (4) 0.0089 (4)
C13 0.0213 (5) 0.0239 (5) 0.0247 (5) 0.0024 (4) 0.0066 (4) 0.0106 (4)
C14 0.0205 (5) 0.0236 (5) 0.0218 (5) 0.0078 (4) 0.0076 (4) 0.0078 (4)
C15 0.0189 (5) 0.0163 (4) 0.0175 (5) 0.0067 (4) 0.0047 (4) 0.0059 (4)
C16 0.0158 (4) 0.0134 (4) 0.0134 (4) 0.0049 (3) 0.0014 (3) 0.0046 (3)
C17 0.0193 (4) 0.0163 (4) 0.0178 (5) 0.0086 (4) 0.0052 (4) 0.0066 (4)
C18 0.0218 (5) 0.0307 (5) 0.0265 (6) 0.0132 (4) 0.0112 (4) 0.0159 (5)
C19 0.0212 (5) 0.0429 (7) 0.0334 (6) 0.0174 (5) 0.0124 (5) 0.0205 (5)
C20 0.0235 (5) 0.0332 (6) 0.0253 (6) 0.0175 (5) 0.0068 (4) 0.0127 (5)
C21 0.0207 (5) 0.0182 (4) 0.0162 (4) 0.0100 (4) 0.0023 (4) 0.0044 (4)
C22 0.0250 (5) 0.0188 (4) 0.0165 (5) 0.0099 (4) 0.0000 (4) 0.0049 (4)
C23 0.0264 (5) 0.0209 (5) 0.0176 (5) 0.0062 (4) 0.0018 (4) 0.0087 (4)
C24 0.0219 (5) 0.0233 (5) 0.0208 (5) 0.0072 (4) 0.0060 (4) 0.0103 (4)
C25 0.0190 (5) 0.0191 (4) 0.0193 (5) 0.0086 (4) 0.0052 (4) 0.0087 (4)
C26 0.0183 (4) 0.0143 (4) 0.0158 (4) 0.0073 (3) 0.0037 (3) 0.0048 (3)
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Geometric parameters (Å, º)

C1—C6 1.3966 (14) C13—C14 1.4157 (16)
C1—C2 1.4013 (13) C13—H13 0.992 (15)
C1—C7 1.4886 (13) C14—C15 1.3720 (15)
C2—C3 1.3966 (13) C14—H14 0.988 (15)
C2—H2 0.984 (13) C15—C16 1.4241 (14)
C3—C4 1.4019 (14) C15—H15 1.010 (13)
C3—C17 1.4902 (14) C17—C18 1.3799 (15)
C4—C5 1.3909 (15) C17—C26 1.4337 (14)
C4—H4 0.995 (13) C18—C19 1.4113 (16)
C5—C6 1.3949 (14) C18—H18 0.990 (15)
C5—H5 0.973 (14) C19—C20 1.3704 (17)
C6—H6 1.001 (13) C19—H19 1.007 (16)
C7—C8 1.3811 (14) C20—C21 1.4174 (16)
C7—C16 1.4309 (14) C20—H20 1.016 (15)
C8—C9 1.4144 (15) C21—C22 1.4212 (15)
C8—H8 0.991 (14) C21—C26 1.4272 (13)
C9—C10 1.3690 (16) C22—C23 1.3634 (16)
C9—H9 0.999 (15) C22—H22 0.992 (14)
C10—C11 1.4161 (15) C23—C24 1.4149 (15)
C10—H10 0.996 (14) C23—H23 1.031 (15)
C11—C12 1.4223 (15) C24—C25 1.3771 (14)
C11—C16 1.4273 (13) C24—H24 1.010 (15)
C12—C13 1.3656 (17) C25—C26 1.4173 (14)
C12—H12 0.998 (14) C25—H25 0.995 (14)
C6—C1—C2 119.05 (9) C15—C14—C13 120.27 (10)
C6—C1—C7 120.75 (9) C15—C14—H14 119.9 (8)
C2—C1—C7 120.18 (8) C13—C14—H14 119.8 (8)
C3—C2—C1 121.27 (9) C14—C15—C16 121.25 (9)
C3—C2—H2 118.1 (7) C14—C15—H15 119.6 (8)
C1—C2—H2 120.5 (7) C16—C15—H15 119.1 (8)
C2—C3—C4 118.73 (9) C15—C16—C11 118.13 (9)
C2—C3—C17 119.48 (9) C15—C16—C7 122.94 (9)
C4—C3—C17 121.74 (9) C11—C16—C7 118.92 (9)
C5—C4—C3 120.47 (9) C18—C17—C26 119.33 (9)
C5—C4—H4 119.7 (8) C18—C17—C3 119.14 (9)
C3—C4—H4 119.8 (8) C26—C17—C3 121.53 (9)
C4—C5—C6 120.26 (9) C17—C18—C19 121.38 (10)
C4—C5—H5 120.7 (8) C17—C18—H18 119.4 (8)
C6—C5—H5 119.0 (8) C19—C18—H18 119.3 (9)
C5—C6—C1 120.18 (9) C20—C19—C18 120.19 (11)
C5—C6—H6 119.3 (8) C20—C19—H19 120.4 (9)
C1—C6—H6 120.5 (7) C18—C19—H19 119.4 (9)
C8—C7—C16 119.38 (9) C19—C20—C21 120.53 (10)
C8—C7—C1 119.62 (9) C19—C20—H20 121.2 (9)
C16—C7—C1 121.00 (8) C21—C20—H20 118.2 (9)
C7—C8—C9 121.24 (10) C20—C21—C22 121.15 (9)
C7—C8—H8 119.6 (8) C20—C21—C26 119.53 (9)
C9—C8—H8 119.1 (8) C22—C21—C26 119.29 (9)
C10—C9—C8 120.22 (10) C23—C22—C21 121.06 (9)
C10—C9—H9 121.2 (8) C23—C22—H22 119.8 (8)
C8—C9—H9 118.6 (8) C21—C22—H22 119.1 (8)
C9—C10—C11 120.51 (9) C22—C23—C24 119.94 (10)
C9—C10—H10 120.8 (8) C22—C23—H23 120.9 (8)
C11—C10—H10 118.7 (8) C24—C23—H23 119.1 (8)
C10—C11—C12 121.23 (9) C25—C24—C23 120.38 (10)
C10—C11—C16 119.64 (9) C25—C24—H24 119.7 (8)
C12—C11—C16 119.13 (9) C23—C24—H24 119.9 (8)
C13—C12—C11 121.13 (10) C24—C25—C26 121.10 (9)
C13—C12—H12 122.3 (8) C24—C25—H25 119.5 (8)
C11—C12—H12 116.6 (8) C26—C25—H25 119.4 (8)
C12—C13—C14 120.05 (10) C25—C26—C21 118.13 (9)
C12—C13—H13 121.2 (9) C25—C26—C17 123.00 (9)
C14—C13—H13 118.8 (8) C21—C26—C17 118.85 (9)
C6—C1—C2—C3 0.09 (15) C12—C11—C16—C7 −179.48 (9)
C7—C1—C2—C3 −178.50 (9) C8—C7—C16—C15 175.10 (9)
C1—C2—C3—C4 −1.45 (15) C1—C7—C16—C15 −5.35 (15)
C1—C2—C3—C17 −178.88 (9) C8—C7—C16—C11 −3.52 (14)
C2—C3—C4—C5 1.18 (15) C1—C7—C16—C11 176.03 (9)
C17—C3—C4—C5 178.55 (10) C2—C3—C17—C18 51.58 (14)
C3—C4—C5—C6 0.46 (16) C4—C3—C17—C18 −125.77 (12)
C4—C5—C6—C1 −1.86 (16) C2—C3—C17—C26 −129.21 (11)
C2—C1—C6—C5 1.58 (15) C4—C3—C17—C26 53.44 (14)
C7—C1—C6—C5 −179.85 (10) C26—C17—C18—C19 −1.65 (17)
C6—C1—C7—C8 −57.09 (13) C3—C17—C18—C19 177.57 (11)
C2—C1—C7—C8 121.46 (11) C17—C18—C19—C20 −1.89 (19)
C6—C1—C7—C16 123.36 (11) C18—C19—C20—C21 2.44 (19)
C2—C1—C7—C16 −58.08 (13) C19—C20—C21—C22 178.91 (11)
C16—C7—C8—C9 3.27 (15) C19—C20—C21—C26 0.53 (17)
C1—C7—C8—C9 −176.28 (9) C20—C21—C22—C23 −175.72 (10)
C7—C8—C9—C10 −0.69 (16) C26—C21—C22—C23 2.66 (15)
C8—C9—C10—C11 −1.62 (16) C21—C22—C23—C24 0.14 (16)
C9—C10—C11—C12 −177.93 (10) C22—C23—C24—C25 −1.92 (17)
C9—C10—C11—C16 1.29 (15) C23—C24—C25—C26 0.83 (17)
C10—C11—C12—C13 177.18 (10) C24—C25—C26—C21 1.96 (15)
C16—C11—C12—C13 −2.04 (16) C24—C25—C26—C17 −179.34 (10)
C11—C12—C13—C14 0.68 (17) C20—C21—C26—C25 174.76 (10)
C12—C13—C14—C15 0.87 (17) C22—C21—C26—C25 −3.65 (14)
C13—C14—C15—C16 −1.04 (16) C20—C21—C26—C17 −4.00 (14)
C14—C15—C16—C11 −0.33 (15) C22—C21—C26—C17 177.59 (9)
C14—C15—C16—C7 −178.95 (10) C18—C17—C26—C25 −174.15 (10)
C10—C11—C16—C15 −177.40 (9) C3—C17—C26—C25 6.64 (15)
C12—C11—C16—C15 1.83 (14) C18—C17—C26—C21 4.54 (15)
C10—C11—C16—C7 1.28 (14) C3—C17—C26—C21 −174.67 (9)
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Footnotes

1

CAS 103068–16–2.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5189).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Click here for additional data file. (19.3KB, cif)

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813002407/tk5189sup1.cif

e-69-0o307-sup1.cif (19.3KB, cif)
Click here for additional data file. (300.8KB, hkl)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002407/tk5189Isup2.hkl

e-69-0o307-Isup2.hkl (300.8KB, hkl)
Click here for additional data file. (6.6KB, cml)

Supplementary material file. DOI: 10.1107/S1600536813002407/tk5189Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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