2-[3-(Naphthalen-2-yl)phen­yl]naph­thal­ene

Wolfenden, M.L.; Dhar, R.K.; Fronczek, F.R.; Watkins, S.F.

doi:10.1107/S1600536813002390

2-[3-(Naphthalen-2-yl)phenyl]naphthalene

M. L. Wolfenden, R. K. Dhar, F. R. Fronczek and S. F. Watkins

The title compound, C₂₆H₁₈, consists of a benzene ring with meta-substituted 2-naphthalene substituents, which are essentially planar [r.m.s. deviations = 0.022 (1) and 0.003 (1) Å]. The conformation is syn, with equivalent torsion angles about the benzene-naphthalene bonds of -36.04 (13) and +34.14 (13)°. The molecule has quasi-C_s molecular symmetry.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536813002390/pv2619sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536813002390/pv2619Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536813002390/pv2619Isup3.cml Supplementary material

CCDC reference: 925233

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R factor = 0.045
wR factor = 0.125
Data-to-parameter ratio = 21.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT411_ALERT_2_C Short Inter H...H Contact  H23    ..  H23     ..       2.12 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.862
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          2
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ?
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         85

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

The crystal and molecular structures of p-oligophenyls have been well investigated (Baker et al., 1990, and references therein), but relatively few studies have appeared concerning the conformational preferences of m-oligophenyls. Two interesting papers were reported, one by Lin & Williams (1975) about the crystal structure of 1,3,5 triphenyl, which serves as a model for m-polyphenyls, showing substituted phenyl groups being twisted about the formal single bonds by +40.7, -37.2, and +36.1° out of the plane of the central ring. The crystal structure of one of the polymorphic forms of hexaphenyl benzene, reported by Bart (1968), has shown that the peripheral rings are not perpendicular to the central ring, but are twisted by about 25°. The molecule was found to be highly distorted as a result of out-of-plane bending of the exocyclic bonds. Therefore, we have studied the structure of 1,3-bis(2-naphthyl)benzene for comparison of its conformation with the previous results.

Title compound I is of quasi-C_s symmetry and consists of a benzene ring with meta-substituted 2-naphthalenes. The benzene ring is nearly planar (C-atoms only, δ_r.m.s. = 0.005 (1) Å), as are the two naphthalenes (δ_r.m.s. = 0.022 (1) and 0.003 (1) Å). The benzene plane and both naphthalene planes are bent with respect to the benzene-naphthalene (BN) bonds: C8 and C18 lie above the benzene plane by 0.039 (2) and 0.040 (1) Å respectively, while C1 lies above its proximate naphthalene plane by 0.016 (1) Å, and C3 lies above its proximate naphthalene plane by 0.085 (1) Å. The naphthalene ring planes are also twisted about the BN bonds with equivalent torsion angles of -36.04 (13)° (C6–C1–C8–C7) and +34.14 (13)° (C4–C3–C18–C17). An isolated and optimized C_s model (Gaussian09; Frisch et al., 2009; DFT:b3lyp/3–21 g) shows a small amount of bending about the BN bonds, with equivalent distances from mean planes C8/C18 = 0.020 Å and C1/C3 = 0.004 Å, and BN torsion angles of ± 43°.

Related literature top

For properties of oligophenyls, see: Bocchinfuso et al. (2009) and for their synthesis, see: Marcinow & Rabideau (1990); Du et al. (1986); Woods et al. (1951). For similar structures, see: Baker et al. (1990); Lin & Williams (1975); Bart (1968). For conformational calculations with GAUSSIAN09, see: Frisch et al. (2009).

Experimental top

Compound I was prepared after Du et al. (1986) and recrystallized from petroleum ether.

Computing details top

Data collection: COLLECT (Nonius 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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).

Figures top

Fig. 1. View of (I) (50% probability displacement ellipsoids)

2-[3-(Naphthalen-2-yl)phenyl]naphthalene top

Crystal data top

C₂₆H₁₈	D_x = 1.269 Mg m⁻³
M_r = 330.4	Melting point: 143.5(5) K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 6568 reflections
a = 25.9304 (3) Å	θ = 2.6–32.6°
b = 8.9300 (1) Å	µ = 0.07 mm⁻¹
c = 14.9377 (2) Å	T = 100 K
V = 3458.95 (7) Å³	Prism, colourless
Z = 8	0.40 × 0.27 × 0.22 mm
F(000) = 1392

Data collection top

Nonius KappaCCD diffractometer	6240 independent reflections
Radiation source: fine-focus sealed tube	4993 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 9 pixels mm^-1	θ_max = 32.6°, θ_min = 2.7°
ϕ and ω scans	h = −39→39
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −13→13
T_min = 0.972, T_max = 0.984	l = −22→22
37425 measured reflections

Refinement top

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	Only H-atom coordinates refined
S = 1.02	w = 1/[σ²(F_o²) + (0.0658P)² + 0.9158P] where P = (F_o² + 2F_c²)/3
6240 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³
0 constraints

Crystal data top

C₂₆H₁₈	V = 3458.95 (7) Å³
M_r = 330.4	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 25.9304 (3) Å	µ = 0.07 mm⁻¹
b = 8.9300 (1) Å	T = 100 K
c = 14.9377 (2) Å	0.40 × 0.27 × 0.22 mm

Data collection top

Nonius KappaCCD diffractometer	6240 independent reflections
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	4993 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.984	R_int = 0.023
37425 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.125	Only H-atom coordinates refined
S = 1.02	Δρ_max = 0.38 e Å⁻³
6240 reflections	Δρ_min = −0.22 e Å⁻³
289 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.

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

	x	y	z	U_iso*/U_eq
C1	0.63414 (3)	0.65124 (10)	0.39203 (6)	0.01689 (17)
C2	0.62992 (3)	0.71392 (10)	0.30628 (6)	0.01694 (16)
H2	0.6484 (5)	0.8056 (15)	0.2934 (8)	0.02*
C3	0.59837 (3)	0.65068 (10)	0.24032 (6)	0.01660 (16)
C4	0.57139 (4)	0.51927 (11)	0.26073 (6)	0.01896 (17)
H4	0.5494 (5)	0.4704 (15)	0.2136 (8)	0.023*
C5	0.57577 (4)	0.45461 (11)	0.34519 (6)	0.02072 (18)
H5	0.5574 (5)	0.3638 (16)	0.3575 (8)	0.025*
C6	0.60671 (4)	0.51962 (11)	0.41055 (6)	0.01975 (18)
H6	0.6101 (5)	0.4717 (15)	0.4700 (9)	0.024*
C7	0.65216 (4)	0.72652 (11)	0.55034 (6)	0.01811 (17)
H7	0.6193 (5)	0.6799 (15)	0.5698 (8)	0.022*
C8	0.66657 (3)	0.72466 (10)	0.46121 (6)	0.01701 (16)
C9	0.71347 (4)	0.79654 (11)	0.43622 (6)	0.01953 (17)
H9	0.7242 (5)	0.7931 (15)	0.3721 (8)	0.023*
C10	0.74404 (4)	0.86589 (11)	0.49847 (6)	0.02031 (18)
H10	0.7772 (5)	0.9160 (15)	0.4807 (8)	0.024*
C11	0.72952 (4)	0.86948 (10)	0.59028 (6)	0.01801 (17)
C12	0.76011 (4)	0.94138 (11)	0.65616 (7)	0.02206 (19)
H12	0.7930 (5)	0.9933 (16)	0.6373 (9)	0.026*
C13	0.74530 (4)	0.94171 (12)	0.74436 (7)	0.0246 (2)
H13	0.7680 (5)	0.9909 (16)	0.7903 (9)	0.03*
C14	0.69902 (4)	0.87049 (13)	0.77044 (6)	0.0248 (2)
H14	0.6888 (5)	0.8669 (17)	0.8349 (9)	0.03*
C15	0.66831 (4)	0.80109 (12)	0.70813 (6)	0.02236 (19)
H15	0.6365 (5)	0.7517 (16)	0.7256 (9)	0.027*
C16	0.68280 (4)	0.79842 (10)	0.61631 (6)	0.01787 (17)
C17	0.54718 (3)	0.72005 (10)	0.10483 (6)	0.01746 (17)
H17	0.5158 (5)	0.6693 (15)	0.1293 (8)	0.021*
C18	0.59332 (3)	0.72319 (10)	0.15125 (6)	0.01630 (16)
C19	0.63624 (3)	0.79954 (11)	0.11308 (6)	0.01800 (17)
H19	0.6705 (5)	0.8014 (15)	0.1453 (8)	0.022*
C20	0.63221 (3)	0.86852 (11)	0.03141 (6)	0.01788 (17)
H20	0.6622 (5)	0.9217 (15)	0.0055 (8)	0.021*
C21	0.58490 (3)	0.86835 (10)	−0.01638 (6)	0.01625 (16)
C22	0.57913 (4)	0.94470 (11)	−0.09892 (6)	0.01963 (18)
H22	0.6099 (5)	0.9976 (15)	−0.1227 (9)	0.024*
C23	0.53253 (4)	0.94754 (12)	−0.14213 (6)	0.02269 (19)
H23	0.5289 (5)	1.0075 (16)	−0.1999 (9)	0.027*
C24	0.48948 (4)	0.87247 (12)	−0.10533 (6)	0.02300 (19)
H24	0.4556 (5)	0.8770 (16)	−0.1362 (9)	0.028*
C25	0.49393 (4)	0.79656 (11)	−0.02576 (6)	0.02032 (18)
H25	0.4636 (5)	0.7474 (16)	0.0014 (8)	0.024*
C26	0.54175 (3)	0.79277 (10)	0.02090 (6)	0.01655 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0171 (4)	0.0180 (4)	0.0155 (4)	0.0020 (3)	0.0003 (3)	−0.0006 (3)
C2	0.0186 (4)	0.0168 (4)	0.0154 (4)	0.0002 (3)	0.0008 (3)	0.0003 (3)
C3	0.0170 (4)	0.0177 (4)	0.0151 (3)	0.0020 (3)	0.0006 (3)	−0.0004 (3)
C4	0.0204 (4)	0.0185 (4)	0.0180 (4)	−0.0005 (3)	−0.0009 (3)	0.0001 (3)
C5	0.0237 (4)	0.0183 (4)	0.0202 (4)	−0.0023 (3)	−0.0001 (3)	0.0023 (3)
C6	0.0232 (4)	0.0189 (4)	0.0172 (4)	0.0007 (3)	0.0001 (3)	0.0028 (3)
C7	0.0170 (4)	0.0212 (4)	0.0161 (4)	−0.0001 (3)	−0.0001 (3)	0.0021 (3)
C8	0.0179 (4)	0.0172 (4)	0.0159 (4)	0.0016 (3)	−0.0009 (3)	0.0010 (3)
C9	0.0195 (4)	0.0220 (4)	0.0171 (4)	−0.0002 (3)	0.0018 (3)	0.0009 (3)
C10	0.0186 (4)	0.0221 (4)	0.0202 (4)	−0.0011 (3)	0.0012 (3)	0.0015 (3)
C11	0.0171 (4)	0.0182 (4)	0.0187 (4)	0.0019 (3)	−0.0011 (3)	0.0009 (3)
C12	0.0209 (4)	0.0212 (4)	0.0241 (4)	0.0006 (3)	−0.0031 (3)	−0.0015 (3)
C13	0.0251 (5)	0.0265 (5)	0.0224 (4)	0.0049 (4)	−0.0058 (4)	−0.0052 (4)
C14	0.0256 (5)	0.0319 (5)	0.0169 (4)	0.0058 (4)	−0.0019 (3)	−0.0024 (4)
C15	0.0218 (4)	0.0288 (5)	0.0165 (4)	0.0020 (4)	0.0005 (3)	0.0010 (3)
C16	0.0175 (4)	0.0205 (4)	0.0156 (4)	0.0022 (3)	−0.0013 (3)	0.0011 (3)
C17	0.0168 (4)	0.0187 (4)	0.0169 (4)	−0.0013 (3)	0.0012 (3)	0.0002 (3)
C18	0.0181 (4)	0.0161 (4)	0.0146 (3)	−0.0001 (3)	0.0004 (3)	−0.0010 (3)
C19	0.0161 (4)	0.0211 (4)	0.0168 (4)	−0.0011 (3)	−0.0007 (3)	−0.0007 (3)
C20	0.0175 (4)	0.0193 (4)	0.0168 (4)	−0.0024 (3)	0.0004 (3)	−0.0003 (3)
C21	0.0179 (4)	0.0157 (4)	0.0152 (4)	0.0001 (3)	0.0000 (3)	−0.0016 (3)
C22	0.0235 (4)	0.0189 (4)	0.0165 (4)	0.0001 (3)	0.0009 (3)	0.0011 (3)
C23	0.0271 (5)	0.0234 (4)	0.0176 (4)	0.0038 (4)	−0.0022 (3)	0.0019 (3)
C24	0.0208 (4)	0.0269 (5)	0.0213 (4)	0.0036 (4)	−0.0047 (3)	−0.0001 (4)
C25	0.0173 (4)	0.0235 (4)	0.0201 (4)	0.0008 (3)	−0.0014 (3)	−0.0009 (3)
C26	0.0170 (4)	0.0172 (4)	0.0154 (4)	0.0009 (3)	0.0000 (3)	−0.0013 (3)

Geometric parameters (Å, º) top

C1—C6	1.4014 (13)	C13—C14	1.4129 (16)
C1—C2	1.4022 (12)	C13—H13	1.005 (14)
C1—C8	1.4850 (12)	C14—C15	1.3729 (14)
C2—C3	1.3995 (12)	C14—H14	0.999 (13)
C2—H2	0.968 (13)	C15—C16	1.4224 (13)
C3—C4	1.3999 (13)	C15—H15	0.970 (14)
C3—C18	1.4856 (12)	C17—C18	1.3830 (12)
C4—C5	1.3922 (13)	C17—C26	1.4190 (12)
C4—H4	1.005 (13)	C17—H17	1.000 (13)
C5—C6	1.3907 (13)	C18—C19	1.4243 (12)
C5—H5	0.959 (14)	C19—C20	1.3707 (12)
C6—H6	0.989 (13)	C19—H19	1.012 (13)
C7—C8	1.3829 (12)	C20—C21	1.4193 (12)
C7—C16	1.4193 (13)	C20—H20	0.990 (13)
C7—H7	0.991 (13)	C21—C22	1.4168 (12)
C8—C9	1.4250 (13)	C21—C26	1.4204 (12)
C9—C10	1.3698 (13)	C22—C23	1.3702 (14)
C9—H9	0.997 (13)	C22—H22	0.994 (13)
C10—C11	1.4226 (13)	C23—C24	1.4136 (14)
C10—H10	1.006 (13)	C23—H23	1.020 (14)
C11—C12	1.4178 (13)	C24—C25	1.3731 (13)
C11—C16	1.4217 (13)	C24—H24	0.992 (13)
C12—C13	1.3723 (14)	C25—C26	1.4229 (13)
C12—H12	1.010 (13)	C25—H25	0.987 (13)

C6—C1—C2	118.39 (8)	C15—C14—C13	120.59 (9)
C6—C1—C8	121.35 (8)	C15—C14—H14	118.9 (8)
C2—C1—C8	120.25 (8)	C13—C14—H14	120.4 (8)
C3—C2—C1	121.85 (8)	C14—C15—C16	120.54 (9)
C3—C2—H2	119.4 (7)	C14—C15—H15	121.1 (8)
C1—C2—H2	118.7 (7)	C16—C15—H15	118.4 (8)
C2—C3—C4	118.50 (8)	C7—C16—C11	119.27 (8)
C2—C3—C18	120.41 (8)	C7—C16—C15	121.95 (9)
C4—C3—C18	121.08 (8)	C11—C16—C15	118.78 (8)
C5—C4—C3	120.28 (8)	C18—C17—C26	121.30 (8)
C5—C4—H4	120.1 (7)	C18—C17—H17	121.9 (7)
C3—C4—H4	119.7 (7)	C26—C17—H17	116.7 (7)
C6—C5—C4	120.68 (9)	C17—C18—C19	119.01 (8)
C6—C5—H5	120.4 (8)	C17—C18—C3	121.10 (8)
C4—C5—H5	119.0 (8)	C19—C18—C3	119.88 (8)
C5—C6—C1	120.28 (8)	C20—C19—C18	120.78 (8)
C5—C6—H6	120.0 (8)	C20—C19—H19	118.9 (7)
C1—C6—H6	119.7 (8)	C18—C19—H19	120.3 (7)
C8—C7—C16	121.51 (9)	C19—C20—C21	120.87 (8)
C8—C7—H7	120.6 (7)	C19—C20—H20	120.2 (7)
C16—C7—H7	117.9 (7)	C21—C20—H20	118.9 (7)
C7—C8—C9	118.52 (8)	C22—C21—C20	121.90 (8)
C7—C8—C1	121.48 (8)	C22—C21—C26	119.12 (8)
C9—C8—C1	120.00 (8)	C20—C21—C26	118.96 (8)
C10—C9—C8	121.31 (8)	C23—C22—C21	120.80 (9)
C10—C9—H9	120.3 (8)	C23—C22—H22	122.1 (7)
C8—C9—H9	118.4 (8)	C21—C22—H22	117.1 (7)
C9—C10—C11	120.75 (9)	C22—C23—C24	120.30 (9)
C9—C10—H10	121.1 (7)	C22—C23—H23	119.3 (7)
C11—C10—H10	118.1 (7)	C24—C23—H23	120.4 (7)
C12—C11—C16	119.28 (8)	C25—C24—C23	120.29 (9)
C12—C11—C10	122.08 (9)	C25—C24—H24	119.8 (8)
C16—C11—C10	118.64 (8)	C23—C24—H24	119.9 (8)
C13—C12—C11	120.71 (9)	C24—C25—C26	120.60 (9)
C13—C12—H12	120.2 (8)	C24—C25—H25	120.5 (8)
C11—C12—H12	119.1 (8)	C26—C25—H25	118.8 (8)
C12—C13—C14	120.10 (9)	C17—C26—C21	119.06 (8)
C12—C13—H13	119.4 (8)	C17—C26—C25	122.01 (8)
C14—C13—H13	120.4 (8)	C21—C26—C25	118.89 (8)

C6—C1—C2—C3	1.51 (13)	C10—C11—C16—C7	−0.07 (13)
C8—C1—C2—C3	−177.83 (8)	C12—C11—C16—C15	−0.31 (13)
C1—C2—C3—C4	−1.46 (13)	C10—C11—C16—C15	179.66 (9)
C1—C2—C3—C18	177.73 (8)	C14—C15—C16—C7	179.43 (9)
C2—C3—C4—C5	0.54 (13)	C14—C15—C16—C11	−0.28 (15)
C18—C3—C4—C5	−178.65 (9)	C26—C17—C18—C19	−0.81 (14)
C3—C4—C5—C6	0.30 (14)	C26—C17—C18—C3	178.19 (8)
C4—C5—C6—C1	−0.24 (15)	C2—C3—C18—C17	−145.04 (9)
C2—C1—C6—C5	−0.64 (14)	C4—C3—C18—C17	34.14 (13)
C8—C1—C6—C5	178.69 (9)	C2—C3—C18—C19	33.95 (12)
C16—C7—C8—C9	0.27 (14)	C4—C3—C18—C19	−146.87 (9)
C16—C7—C8—C1	−179.14 (8)	C17—C18—C19—C20	−0.30 (14)
C6—C1—C8—C7	−36.04 (13)	C3—C18—C19—C20	−179.31 (8)
C2—C1—C8—C7	143.28 (9)	C18—C19—C20—C21	1.32 (14)
C6—C1—C8—C9	144.56 (9)	C19—C20—C21—C22	177.04 (9)
C2—C1—C8—C9	−36.12 (13)	C19—C20—C21—C26	−1.24 (14)
C7—C8—C9—C10	0.22 (14)	C20—C21—C22—C23	−177.55 (9)
C1—C8—C9—C10	179.64 (9)	C26—C21—C22—C23	0.72 (14)
C8—C9—C10—C11	−0.64 (15)	C21—C22—C23—C24	−0.75 (15)
C9—C10—C11—C12	−179.48 (9)	C22—C23—C24—C25	0.27 (15)
C9—C10—C11—C16	0.55 (14)	C23—C24—C25—C26	0.23 (15)
C16—C11—C12—C13	0.59 (14)	C18—C17—C26—C21	0.87 (13)
C10—C11—C12—C13	−179.38 (9)	C18—C17—C26—C25	−177.02 (9)
C11—C12—C13—C14	−0.27 (15)	C22—C21—C26—C17	−178.18 (8)
C12—C13—C14—C15	−0.34 (16)	C20—C21—C26—C17	0.15 (13)
C13—C14—C15—C16	0.61 (16)	C22—C21—C26—C25	−0.22 (13)
C8—C7—C16—C11	−0.34 (14)	C20—C21—C26—C25	178.10 (8)
C8—C7—C16—C15	179.94 (9)	C24—C25—C26—C17	177.64 (9)
C12—C11—C16—C7	179.96 (9)	C24—C25—C26—C21	−0.25 (14)

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈
M_r	330.4
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	100
a, b, c (Å)	25.9304 (3), 8.9300 (1), 14.9377 (2)
V (Å³)	3458.95 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.40 × 0.27 × 0.22

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.972, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	37425, 6240, 4993
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.758

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.125, 1.02
No. of reflections	6240
No. of parameters	289
H-atom treatment	Only H-atom coordinates refined
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.22

Computer programs: COLLECT (Nonius 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

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2-[3-(Naphthalen-2-yl)phen­yl]naph­thal­ene

Supporting information

Key indicators

checkCIF/PLATON results

2-[3-(Naphthalen-2-yl)phenyl]naphthalene