Crystal structure of 2-meth­oxy-1-nitro­naphthalene

Hasna Yassine; Mostafa Khouili; Lahcen El Ammari; Mohamed Saadi; El Mostafa Ketatni

doi:10.1107/S2056989015016114

. 2015 Sep 12;71(Pt 10):o701–o702. doi: 10.1107/S2056989015016114

Crystal structure of 2-methoxy-1-nitronaphthalene

Hasna Yassine ^a, Mostafa Khouili ^a,^*, Lahcen El Ammari ^b, Mohamed Saadi ^b, El Mostafa Ketatni ^c

PMCID: PMC4647346 PMID: 26594431

Abstract

The asymmetric unit of the title compound, C₁₁H₉NO₃, contains two molecules, A and B. In molecule A, the dihedral angle between the planes of the naphthalene ring system (r.m.s. deviation = 0.003 Å) and the nitro group is 89.9 (2)°, and the C atom of the methoxy group deviates from the naphthyl plane by 0.022 (2) Å. Equivalent data for molecule B are 0.008 Å, 65.9 (2)° and −0.198 (2) Å, respectively. In the crystal, molecules are linked by weak C—H⋯O interactions, forming [100] chains of alternating A and B molecules. Weak aromatic π–π stacking contacts, with a range of centroid–centroid distances from 3.5863 (9) to 3.8048 (9) Å, are also observed.

Keywords: crystal structure, naphthalene derivative, weak C—H⋯O interactions, π–π stacking

Related literature

For biological activities of naphthalene derivatives, see: Wright et al. (2000 ▸); Rokade & Sayyed (2009 ▸); Upadhayaya et al. (2010 ▸). For the title compound as an intermediate in the synthesis of antipyretic drugs, see: Stoylkova et al. (2000 ▸); Govindarajana et al. (2011 ▸); Kirumakki et al. (2004 ▸); Yadav et al. (1998 ▸). For a related structure, see: Wannalerse et al. (2013 ▸).

Experimental

Crystal data

C₁₁H₉NO₃
M _r = 203.19
Triclinic,
a = 9.1291 (4) Å
b = 10.2456 (4) Å
c = 10.5215 (4) Å
α = 86.390 (2)°
β = 82.964 (2)°
γ = 85.801 (2)°
V = 972.63 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.39 × 0.32 × 0.24 mm

Data collection

Bruker X8 APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T _min = 0.676, T _max = 0.746
34901 measured reflections
5450 independent reflections
3446 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.141
S = 1.04
5450 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); 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: PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015016114/hb7477sup1.cif

e-71-0o701-sup1.cif^{(1MB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015016114/hb7477Isup2.hkl

e-71-0o701-Isup2.hkl^{(433.5KB, hkl)}

Click here for additional data file.^{(3.9KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015016114/hb7477Isup3.cml

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

. DOI: 10.1107/S2056989015016114/hb7477fig1.tif

A view of the molecule of the title compound, showing displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small circles.

Click here for additional data file.^{(2MB, tif)}

. DOI: 10.1107/S2056989015016114/hb7477fig2.tif

Partial crystal packing for the title compound showing molecules linked by hydrogen bonds as blue dashed lines and π–π contacts between the naphthalene rings (red dashed lines).

CCDC reference: 1421062

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

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
C4H4O5ⁱ	0.93	2.57	3.409(2)	150
C11H11AO5ⁱⁱ	0.96	2.60	3.462(3)	150

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

Acknowledgments

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements and the University Sultan Moulay Slimane, Beni-Mellal, for financial support.

supplementary crystallographic information

S1. Comment

Naphthalene derivatives have been extensively employed in many fields, for example, as a colorant, explosive, disinfectant, insecticide, auxin plant hormone and play a role in the chemical defence against biological (Wright et al., 2000) and have diverse and interesting antibiotic properties (Rokade & Sayyed, 2009; Upadhayaya et al. 2010). 2-Methoxynaphthalene is an important intermediate used in the production of naproxen. It is widely used a non-steroidal anti-inflammatory, analgesic and antipyretic drug (Stoylkova et al., 2000, Govindarajana et al., 2011, Kirumakki et al., 2004; Yadav et al., 1998). Nitration of 1-methoxynaphthalene with bismuth nitrate in CH₂Cl₂ gives a compound (I) and describes its structure here.

The asymmetric unit of the title compound consists of two crystallographically independent molecules of nearly similar geometry as shown in Fig. 1. Bond lengths and angles of the title compound are comparable with that found in the similar structure (Wannalerse et al., 2013). In the first (O1O2O3N1C1–C11) and second (O4O5O6N2C12–C22) molecules, the dihedral angles between the nitro group and the attached naphthalene system are 89.9 (2)° and 65.9 (2)°, respectively. The two naphthalene rings belonging to the both molecules form a dihedral angle of 72.02 (5)°.

In the crystal, the molecules are linked together by weak C—H···O interactions. Moreover, the π–π contacts between the naphthalene rings, may further consolidate the structure, with range of centroid– centroid distances = 3.5863 (9)—3.8048 (9) Å.

S2. Experimental

2-Methoxynaphtalene (500 mg, 3.164 mmol) and silica gel (500 mg) was added to a suspension of bismuth nitrate pentahydrate (1.2 eqv.) in CH₂Cl₂ (20 ml). The mixture was refluxed for 6 h. After cooling to room temperature, the reaction mixture was filtered and watched with CH₂Cl₂, the filtrate obtained was concentrated, and the resulting residue was purified by column chromatography using EtOAc-Hexane (1:9 v/v). The title compound was recrystallized from the solvent mixture ethyl acetate/hexane to yield orange block crystals (yield: 74%).