Crystal structure of 2,2′-bis­[(2-chloro­benz­yl)­oxy]-1,1′-bi­naphthalene

Rajamani Raja; Mani Jayanthi; Perumal Rajakumar; A SubbiahPandi

doi:10.1107/S2056989015014322

. 2015 Aug 6;71(Pt 9):o637–o638. doi: 10.1107/S2056989015014322

Crystal structure of 2,2′-bis[(2-chlorobenzyl)oxy]-1,1′-binaphthalene

Rajamani Raja ^a, Mani Jayanthi ^b, Perumal Rajakumar ^b, A SubbiahPandi ^a,^*

PMCID: PMC4555433 PMID: 26396878

Abstract

In the title binaphthyl compound, C₃₄H₂₄Cl₂O₂, the dihedral angle between the two naphthyl ring systems (r.m.s. deviations = 0.016 and 0.035 Å) is 76.33 (8)°. The chlorophenyl rings make dihedral angles of 58.15 (12) and 76.21 (13)° with the naphthyl ring to which they are linked. The dihedral angle between the planes of the two chlorophenyl rings is 27.66 (16)°. In the crystal, C—H⋯O hydrogen bonds link molecules into chains propagating along [1-10]. The chains are linked by C—H⋯π interactions, forming a three-dimensional framework.

Keywords: crystal structure, binaphthyl, antimicrobials, antibiotic properties, minimum toxicity, hydrogen bonding

Related literature

For the synthesis and biological activity of naphthalene compounds, see: Upadhayaya et al. (2010 ▸); Rokade & Sayyed (2009 ▸). For the crystal structure of a very similar compound, 4,4′-{[[1,1′-binaphthalene]-2,2′-diylbis(oxy)]bis(methylene)}dibenzonitrile, see: Fu & Zhao (2007 ▸). graphic file with name e-71-0o637-scheme1.jpg

Experimental

Crystal data

C₃₄H₂₄Cl₂O₂
M _r = 535.43
Monoclinic,
a = 11.1983 (3) Å
b = 14.6094 (4) Å
c = 16.3263 (4) Å
β = 92.622 (2)°
V = 2668.19 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▸) T _min = 0.909, T _max = 0.921
10688 measured reflections
4153 independent reflections
3804 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.116
S = 1.04
4153 reflections
343 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.47 e Å⁻³
Absolute structure: Flack (1983 ▸), 1709 (76%) Friedel pairs
Absolute structure parameter: −0.01 (8)

Data collection: APEX2 (Bruker, 2008 ▸); cell refinement: SAINT (Bruker, 2008 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015014322/su5184sup1.cif

e-71-0o637-sup1.cif^{(25.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015014322/su5184Isup2.hkl

e-71-0o637-Isup2.hkl^{(203.5KB, hkl)}

Click here for additional data file.^{(9.4KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015014322/su5184Isup3.cml

Click here for additional data file.^{(1.4MB, tif)}

. DOI: 10.1107/S2056989015014322/su5184fig1.tif

The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.^{(1.7MB, tif)}

a . DOI: 10.1107/S2056989015014322/su5184fig2.tif

The crystal packing of the title compound, viewed along the a axis. The intermolecular interactions are shown as dashed lines (see Table 1).

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S2056989015014322/su5184fig3.tif

A partial view of the crystal packing of the title compound, showing the C—H⋯π interactions as dashed lines (see Table 1).

CCDC reference: 1415827

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

Cg5 is the centroid of the C19C24 ring.

DHA	DH	HA	D A	DHA
C22H22O1ⁱ	0.93	2.57	3.413(4)	151
C4H4Cg5ⁱⁱ	0.93	2.74	3.433(4)	132
C33H33Cg5ⁱⁱⁱ	0.93	2.92	3.781(6)	155

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

RR and ASP thank the Department of Chemistry, IIT, Chennai, India, for the X-ray data collection.

supplementary crystallographic information

S1. Comment

Naphthalene derivatives has been identified as new range of potent antimicrobials effective against a wide range of human pathogens. They occupy a central place among medicinally important compounds due to their diverse and interesting antibiotic properties with minimum toxicity (Rokade & Sayyed, 2009; Upadhayaya et al. 2010). Herein, we report on the synthesis and crystal structure of a new binaphthyl derivative.

The molecular structure of the title compound is shown in Fig. 1. The chlorophenyl ring (C1—C6) make a dihedral angle of 58.15 (12) ° with the naphthalene ring system (C8—C17), while the other chlorophenyl ring (C29—C34) makes a dihedral angle of 76.21 (13) ° with the naphthalene ring system (C18—C27). The two naphthalene rings are inclined to one another by 76.33 (8)° and the two chlorophenyl rings by 27.66 (16) °. Atoms O1 and O2 deviate from their respective naphthalene ring by 0.144 and 0.138 Å, respectively. The two naphthalene rings are connected at bond C17—C18, with torsion angle C19—C18—C17—C16 = 75.7 (3) °, indicating a (+) syn-clinal conformation for this group.

In the crystal, C—H···O hydrogen bonds link molecules into chains propagating along [110]; Table 1 and Fig. 2. The chains are linked by C—H···π interactions forming a three-dimensional framework (Table 1 and Fig. 3).

S2. Synthesis and crystallization

The title compound was synthesized by reacting two equivalents of 2-chloro benzylbromide with one equivalent of S-BINOL in dry DMF in the presence of K₂CO₃ at 333 K, which successfully provided the pure title product as a colourless solid. The product was dissolved in chloroform and heated for 2 min. The resulting solution was subjected to crystallization by slow evaporation of the solvent for 18 h resulting in the formation of single crystals.

S3. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The C-bound H atoms were positioned geometrically and allowed to ride on their parent atoms: C—H = 0.93 - 0.97 Å with U_iso(H) = 1.2U_eq(C).