9-Chloro­methyl-9-[(9H-fluoren-9-yl)meth­yl]-9H-fluorene

Qun Shen; Shu-Qiang Yu; Bin-Bin Hu; Ping Lu

doi:10.1107/S1600536808012117

. 2008 May 3;64(Pt 6):o996. doi: 10.1107/S1600536808012117

9-Chloromethyl-9-[(9H-fluoren-9-yl)methyl]-9H-fluorene

Qun Shen ^a, Shu-Qiang Yu ^a, Bin-Bin Hu ^a, Ping Lu ^a,^*

PMCID: PMC2961556 PMID: 21202721

Abstract

In the title compound, C₂₈H₂₁Cl, the dihedral angle between the two fluorene ring systems is 71.97 (4)°. There is an intramolecular C—H⋯Cl hydrogen bond. In the crystal structure, the centroid-to-centroid distance between stacked fluorene ring systems is ca 4.22 Å, which indicates that there are no π–π stacking interactions between them.

Related literature

For general background, see: Chun et al. (2003 ▶); Kim et al. (1998 ▶); Muller et al. (2003 ▶); Saragi et al. (2004 ▶).

Experimental

Crystal data

C₂₈H₂₁Cl
M _r = 392.90
Monoclinic,
a = 8.4346 (17) Å
b = 26.368 (5) Å
c = 9.1162 (18) Å
β = 94.08 (3)°
V = 2022.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 298 (2) K
0.35 × 0.29 × 0.22 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: none
16094 measured reflections
3646 independent reflections
2747 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.133
S = 1.08
3646 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012117/xu2420sup1.cif

e-64-0o996-sup1.cif^{(23.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012117/xu2420Isup2.hkl

e-64-0o996-Isup2.hkl^{(178.8KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C27—H27A⋯Cl1	0.97	2.68	3.075 (2)	105

Open in a new tab

Acknowledgments

The authors thank the National Natural Science Foundation of China (20674070) and the Natural Science Foundation of Zhejiang Province, China (R404109).

supplementary crystallographic information

Comment

Fluorene derivatives, have attracted much attention due to their potential utilities in organic lightemitting devices (Muller et al., 2003), organic phototransistors (Saragi et al., 2004), nonlinear optics (Kim et al., 1998) and photochromic materials (Chun et al., 2003). The title compound (hereinafter abbreviated to fmcf) is one of fluorene derivatives.

The asymmetric unit of the title compound contains one fmcf molecule (Fig. 1). The chloromethyl group is attached on the C-9 position of one fluorene ring. Two fluorene rings are linked together through a methylene carbon atom, and the dihedral angle between the two fluorene rings is 71.97 (4)°. There is intramolecular C–H···Cl hydrogen bond with distance of 3.075 (2) Å (Table 1), while the intermolecular C–H···Cl contacts are of 3.573 (2) Å, which is not viewed as C–H···Cl hydrogen bond. The centroid to centroid distance between stacked fluorene rings is ca. 4.22 Å, which is very long and prevents π···π stacking (Fig. 2). All bond lengths and angles are normal.

Experimental

All chemicals were of analytic grade quality obtained from commercial sources and used as received, unless stated otherwise. To a solution of fluorene (1.66 g, 10 mmol) in dry THF (40 ml) was added a hexane solution of n-butylithium (4 ml, 2.5 M, 10 mmol) under nitrogen at -78 °C, the mixture was stirred for 1 h. A solution of PCl₃ (2 mmol) in THF (10 ml) was then added. After stirring for another 1 h, the mixture was cooling slowly to room temperature, and kept stirring overnight. To the mixture was added dichloromethane (20 ml) and stirred for 1 h. The solvent was evaporated under reduced pressure. The crude products were purified by columnchromatography (silica gel) using n-hexane/dichloromethane as eluent. The title compound was obtained as white solid in 31% yield. Colorless single crystals were grown from a CH₂Cl₂ solution of the compound.