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

Mark L Wolfenden; Raj K Dhar; Frank R Fronczek; Steven F Watkins

doi:10.1107/S1600536813002390

. 2013 Jan 31;69(Pt 2):o308. doi: 10.1107/S1600536813002390

2-[3-(Naphthalen-2-yl)phenyl]naphthalene¹

Mark L Wolfenden ^a, Raj K Dhar ^a, Frank R Fronczek ^a,^*, Steven F Watkins ^a

PMCID: PMC3569827 PMID: 23424573

Abstract

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.

Related literature

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 ▶); Tummala et al. (2013 ▶). For conformational calculations with GAUSSIAN09, see: Frisch et al. (2009 ▶). graphic file with name e-69-0o308-scheme1.jpg

Experimental

Crystal data

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

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T _min = 0.972, T _max = 0.984
37425 measured reflections
6240 independent reflections
4993 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.125
S = 1.02
6240 reflections
289 parameters
Only H-atom coordinates refined
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.22 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/S1600536813002390/pv2619sup1.cif

e-69-0o308-sup1.cif^{(19.3KB, cif)}

Click here for additional data file.^{(299.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002390/pv2619Isup2.hkl

e-69-0o308-Isup2.hkl^{(299.4KB, hkl)}

Click here for additional data file.^{(6.6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813002390/pv2619Isup3.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

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°.

Experimental

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

Figures

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

Crystal data

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

Open in a new tab

Data collection

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

Open in a new tab

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)] = 0.045	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

Open in a new tab

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.

Open in a new tab

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

	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)

Open in a new tab

Atomic displacement parameters (Å²)

	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)

Open in a new tab

Geometric parameters (Å, º)

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)

Open in a new tab

Footnotes

CAS 103068–17–3.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2619).

References

Baker, K. N., Fratini, A. V. & Adams, W. W. (1990). Polymer, 31, 1623–1631.
Bart, J. C. J. (1968). Acta Cryst. B24, 1277–1287.
Bocchinfuso, G., Mazzuca, C., Palleschi, A., Pizzoferrato, R. & Tagliatesta, P. (2009). J. Phys. Chem. A, 113, 14887–14895. [DOI] [PubMed]
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.
Du, C. J. F., Hart, H. & Ng, K. K. D. (1986). J. Org. Chem. 51, 3162–3165.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.
Frisch, M. J., et al. (2009). GAUSSIAN09 Gaussian, Inc., Wallingford, CT, USA.
Lin, Y. C. & Williams, D. E. (1975). Acta Cryst. B31, 318–320.
Marcinow, Z. & Rabideau, P. (1990). J. Org. Chem. 55, 3812–3816.
Nonius (2000). COLLECT Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
Tummala, M., Dhar, R. K., Fronczek, F. R. & Watkins, S. F. (2013). Acta Cryst. E69, o307. [DOI] [PMC free article] [PubMed]
Woods, G. F., Reed, F. T., Arthur, T. E. & Ezekiel, H. (1951). J. Am. Chem. Soc. 73, 3854–3856.

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/S1600536813002390/pv2619sup1.cif

e-69-0o308-sup1.cif^{(19.3KB, cif)}

Click here for additional data file.^{(299.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002390/pv2619Isup2.hkl

e-69-0o308-Isup2.hkl^{(299.4KB, hkl)}

Click here for additional data file.^{(6.6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813002390/pv2619Isup3.cml

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

[bb1] Baker, K. N., Fratini, A. V. & Adams, W. W. (1990). Polymer, 31, 1623–1631.

[bb2] Bart, J. C. J. (1968). Acta Cryst. B24, 1277–1287.

[bb3] Bocchinfuso, G., Mazzuca, C., Palleschi, A., Pizzoferrato, R. & Tagliatesta, P. (2009). J. Phys. Chem. A, 113, 14887–14895. [DOI] [PubMed]

[bb4] Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.

[bb5] Du, C. J. F., Hart, H. & Ng, K. K. D. (1986). J. Org. Chem. 51, 3162–3165.

[bb6] Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.

[bb7] Frisch, M. J., et al. (2009). GAUSSIAN09 Gaussian, Inc., Wallingford, CT, USA.

[bb8] Lin, Y. C. & Williams, D. E. (1975). Acta Cryst. B31, 318–320.

[bb9] Marcinow, Z. & Rabideau, P. (1990). J. Org. Chem. 55, 3812–3816.

[bb10] Nonius (2000). COLLECT Nonius BV, Delft, The Netherlands.

[bb11] Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.

[bb12] Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

[bb14] Tummala, M., Dhar, R. K., Fronczek, F. R. & Watkins, S. F. (2013). Acta Cryst. E69, o307. [DOI] [PMC free article] [PubMed]

[bb13] Woods, G. F., Reed, F. T., Arthur, T. E. & Ezekiel, H. (1951). J. Am. Chem. Soc. 73, 3854–3856.

PERMALINK

2-[3-(Naphthalen-2-yl)phenyl]naphthalene¹

Mark L Wolfenden

Raj K Dhar

Frank R Fronczek

Steven F Watkins

Abstract

Related literature

Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

Special details

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

Atomic displacement parameters (Å²)

Geometric parameters (Å, º)

Footnotes

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

Cite

Add to Collections

PERMALINK

2-[3-(Naphthalen-2-yl)phen­yl]naph­thal­ene1

Mark L Wolfenden

Raj K Dhar

Frank R Fronczek

Steven F Watkins

Abstract

Related literature

Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

Special details

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

Atomic displacement parameters (Å2)

Geometric parameters (Å, º)

Footnotes

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

Similar articles

Cited by other articles

Links to NCBI Databases

2-[3-(Naphthalen-2-yl)phenyl]naphthalene¹

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

Atomic displacement parameters (Å²)