Bis(3-bromo­methyl-2-meth­oxy-1-naphth­yl)methane

Jie-Wei Luo; Li Zhou; Rui He; Gui-Yu Wang; Da-Bin Qin

doi:10.1107/S1600536808027529

. 2008 Aug 30;64(Pt 9):o1861. doi: 10.1107/S1600536808027529

Bis(3-bromomethyl-2-methoxy-1-naphthyl)methane

Jie-Wei Luo ^a, Li Zhou ^a, Rui He ^a, Gui-Yu Wang ^a, Da-Bin Qin ^a,^*

PMCID: PMC2960732 PMID: 21201830

Abstract

The title compound, C₂₅H₂₂Br₂O₂, crystallizes with two molecules in the asymmetric unit. In each independent molecule, the two naphthalene ring systems are nearly perpendicular to one another, with dihedral angles of 85.6 (1) and 86.2 (1)°. The crystal structure is stabilized by C—H⋯π interactions, and inter- and intramolecular C—H⋯O and C—H⋯Br hydrogen bonds.

Related literature

For the synthesis, see: Failla et al. (1993 ▶). For a related structure, see: Liu et al. (2006 ▶). For related literature, see: Fonge et al. (2007 ▶); Georghiou et al. (1996 ▶); Haynes et al. (2006 ▶); Kano et al. (1995 ▶); Kondekar & Potlis (1973 ▶).

Experimental

Crystal data

C₂₅H₂₂Br₂O₂
M _r = 514.25
Triclinic,
a = 10.6812 (3) Å
b = 11.1429 (4) Å
c = 18.4311 (6) Å
α = 99.327 (1)°
β = 98.326 (1)°
γ = 96.296 (1)°
V = 2121.84 (12) Å³
Z = 4
Mo Kα radiation
μ = 3.84 mm⁻¹
T = 153 (2) K
0.54 × 0.36 × 0.34 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (SADABS; Siemens, 1996 ▶) T _min = 0.208, T _max = 0.271
20944 measured reflections
9619 independent reflections
6284 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.209
S = 1.01
9619 reflections
528 parameters
H-atom parameters constrained
Δρ_max = 1.01 e Å⁻³
Δρ_min = −1.48 e Å⁻³

Data collection: RAPID-AUTO (Rigaku/MSC 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027529/pv2087sup1.cif

e-64-o1861-sup1.cif^{(33.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027529/pv2087Isup2.hkl

e-64-o1861-Isup2.hkl^{(470.4KB, 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
C12—H12A⋯Br1ⁱ	0.99	2.91	3.867 (6)	164
C37—H37B⋯O2ⁱⁱ	0.99	2.56	3.384 (8)	141
C8—H8⋯O2	0.95	2.26	3.197 (7)	168
C11—H11C⋯Br1	0.98	2.86	3.575 (7)	131
C21—H21⋯O1	0.95	2.25	3.145 (7)	156
C33—H33⋯O4	0.95	2.32	3.244 (7)	164
C46—H46⋯O3	0.95	2.26	3.197 (7)	168
C5—H5⋯Cg4ⁱⁱⁱ	0.95	2.63	3.511 (7)	155
C49—H49B⋯Cg7^iv	0.98	2.73	3.505 (7)	136
C43—H43⋯Cg1	0.95	2.71	3.625 (7)	161

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg1, Cg4 and Cg7 are the centroids of atoms C1–C4,C9,C10, C17–C22 and C26–C29,C34,C35, respectively.

Acknowledgments

The authors thank the Scientific Research Fund Projects of China West Normal University (grant No. 06B003) and the Youth Fund Projects of Sichuan Educational Department (grant No. 2006B039).

supplementary crystallographic information

Comment

Pamoic acid and its derivatives have attracted the attention of some scienctists (Kano et al., 1995; Fonge et al., 2007). The involved role has been performed in the pharmaceutical industry for the preparation of medicaments for the treatment of diseases (Haynes et al., 2006). We have synthesized a derivative compound of pamoci acid according to the reported literature (Georghiou et al., 1996; Kondekar & Potlis, 1973; Failla et al., 1993). By reference to the crystal structure reported in the literature (Liu et al., 2006), we report the crystal structure of the title compound, (I), in this paper.

The title compound crystallizes in the triclinic space group P-1 with two independent molecules in an asymmetric unit (Fig. 1). In each molecule, the two naphthalene ring systems are nearly perpendicular to one another. The dihedral angle between the C1—C10 and C14—C23 planes is 85.6 (1)° and that between the C26—C35 and C39—C48 planes is 86.2 (1)°. The crystal packing is stabilized by C—H···π interactions, intermolecular and intramolecular C—H···O and C—H···Br hydrogen bonds (Table 1).

Experimental

The title compound was prepared according to the reported procedure of Failla et al. (1993). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from dichloromethane.