3,11-Dibromo-14-(4-chloro­phen­yl)-14H-dibenzo[a,j]xanthene dimethyl­formamide monosolvate

Yong Bin Song; Bo Liu

doi:10.1107/S1600536812016200

. 2012 Apr 21;68(Pt 5):o1460. doi: 10.1107/S1600536812016200

3,11-Dibromo-14-(4-chlorophenyl)-14H-dibenzo[a,j]xanthene dimethylformamide monosolvate

Yong Bin Song ^a, Bo Liu ^a,^*

PMCID: PMC3344574 PMID: 22590336

Abstract

In the title compound, C₂₇H₁₅Br₂ClO·C₃H₇NO, the xanthene moiety has a flattened boat conformation with a folding angle between the naphthalene units of 9.46 (3)°. The mean planes of the xanthene system and its 4-chlorophenyl substituent are nearly perpendicular [dihedral angle = 89.43 (5)°]. The dimethylformamide solvent molecule is disordered over two sets of sites with an occupancy ratio of 0.520 (11):0.480 (11).

Related literature

For related structures and the preparation of the title compound, see: Wu et al. (2009 ▶); Seethalakshmi et al. (2006 ▶). For the biological activity of benzoxanthene derivatives, see: Lambert et al. (1997 ▶); Hideo (1981 ▶); Poupelin et al. (1978 ▶). For related structures, see: Cai et al. (2009 ▶); Lu et al. (2008 ▶); Rahmani et al. (2009 ▶); Dalla Via et al. (2008 ▶); Gaurrand et al. (2006 ▶); Petit et al. (2007 ▶).

Experimental

Crystal data

C₂₇H₁₅Br₂ClO·C₃H₇NO
M _r = 623.74
Triclinic,
a = 10.8558 (12) Å
b = 10.9385 (12) Å
c = 11.8946 (13) Å
α = 74.443 (1)°
β = 80.967 (1)°
γ = 71.448 (1)°
V = 1286.0 (2) Å³
Z = 2
Mo Kα radiation
μ = 3.29 mm⁻¹
T = 293 K
0.28 × 0.26 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.415, T _max = 0.518
8696 measured reflections
4522 independent reflections
2902 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.091
S = 1.03
4522 reflections
375 parameters
55 restraints
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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 datablock(s) I, global. DOI: 10.1107/S1600536812016200/ld2054sup1.cif

e-68-o1460-sup1.cif^{(22.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016200/ld2054Isup2.hkl

e-68-o1460-Isup2.hkl^{(212.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812016200/ld2054Isup3.cml

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

Acknowledgments

The authors thank Zhanhua Su for help with the data collection.

supplementary crystallographic information

Comment

Derivatives of benzoxanthenes have received much attention due to their wide range of biological and pharmacological activities, such as antiviral (Lambert et al., 1997), antibacterial (Hideo, 1981), and anti-inflammatory (Poupelin et al., 1978). In the present paper we describe the crystal structure of the title compound.

The molecular structure of the compound is shown in the Figure 1. The chlorophenyl substituent (C12–C17) at C11 forms dihedral angle of 89.43 (5)° with the mean plane of the xanthene ring system. The pyran ring (O1/C9/C10/C11/C18/C19) adopts a boat conformation with the O1 and C11 displaced by 0.112 and 0.253 (4) Å, respectively, from the mean plane of the rest of the atoms.

The packing is characterized by Cl···Br contacts and π···π stacking interactions. The distance between the Cl and Br atoms is 3.5668 (9) Å; The angles C1—Br1···Cl1 and C15—Cl1···Br1 are 161.43 (1)° and 85.97 (1)°, respectively. Some π···π stacking interactions between phenyl rings (containing Br1 and Br2, respectively) were detected with the centroid-to-centroid distance of 3.688 (2) Å. Short C-H···O contacts take place between the title molecule and the solvent.

Experimental

A solution of the 6-bromo-2-naphthol (2.2 g, 10 mmol), and 4-chloro-benzaldehyde (0.7 g, 5 mmol), acetic acid (5 ml) was refluxed with 1 ml of hydrochloric acid for two hours (Wu et al., 2009). The system was cooled to room temperature, and the formed precipitate was filtered and washed with water. The product was recrystallized from the mixed solution of ethanol and dimethylformamide (DMF), and yielded raw crystals (2.2 g, yield 81%). The colourless single crystals of the title compound were grown by recystallization from DMF solution.