organic compounds
of 2-methoxy-1-nitronaphthalene
aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, BP 523, 23000 Béni-Mellal, Morocco, bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP 1014, Rabat, Morocco, and cLaboratoire de Spectrochimie Applique et Environnement, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, BP 523, 23000 Béni-Mellal, Morocco
*Correspondence e-mail: m.khouili@usms.ma
The 11H9NO3, 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.
of the title compound, CCCDC reference: 1421062
1. 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).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2009); cell 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).
Supporting information
CCDC reference: 1421062
10.1107/S2056989015016114/hb7477sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015016114/hb7477Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015016114/hb7477Isup3.cml
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
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%).All H atoms could be located in a difference Fourier map. However, they were placed in calculated positions with C—H = 0.93–0.96 Å, and refined as riding on their parent atoms with Uiso(H) = 1.2 Ueq for aromatic and Uiso(H) = 1.5 Ueq (C) for methyl. Two outlier reflections, (-7 3 0) and (-1 - 3 2), were omitted in the last cycles of refinement.
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).C11H9NO3 | Z = 4 |
Mr = 203.19 | F(000) = 424 |
Triclinic, P1 | Dx = 1.388 Mg m−3 |
a = 9.1291 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.2456 (4) Å | Cell parameters from 3506 reflections |
c = 10.5215 (4) Å | θ = 1.7–30.0° |
α = 86.390 (2)° | µ = 0.10 mm−1 |
β = 82.964 (2)° | T = 296 K |
γ = 85.801 (2)° | Block, orange |
V = 972.63 (7) Å3 | 0.39 × 0.32 × 0.24 mm |
Bruker X8 APEXII CCD diffractometer | 5450 independent reflections |
Radiation source: fine-focus sealed tube | 3446 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scans | θmax = 29.6°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −12→12 |
Tmin = 0.676, Tmax = 0.746 | k = −14→14 |
34901 measured reflections | l = −14→14 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.0511P)2 + 0.2462P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.141 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.20 e Å−3 |
5450 reflections | Δρmin = −0.15 e Å−3 |
272 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.011 (2) |
C11H9NO3 | γ = 85.801 (2)° |
Mr = 203.19 | V = 972.63 (7) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.1291 (4) Å | Mo Kα radiation |
b = 10.2456 (4) Å | µ = 0.10 mm−1 |
c = 10.5215 (4) Å | T = 296 K |
α = 86.390 (2)° | 0.39 × 0.32 × 0.24 mm |
β = 82.964 (2)° |
Bruker X8 APEXII CCD diffractometer | 5450 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3446 reflections with I > 2σ(I) |
Tmin = 0.676, Tmax = 0.746 | Rint = 0.038 |
34901 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.20 e Å−3 |
5450 reflections | Δρmin = −0.15 e Å−3 |
272 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.82138 (17) | 0.83303 (15) | 0.59386 (15) | 0.0445 (3) | |
C2 | 0.76837 (19) | 0.92960 (16) | 0.67524 (16) | 0.0512 (4) | |
C3 | 0.8714 (2) | 0.99956 (17) | 0.72711 (17) | 0.0582 (4) | |
H3 | 0.8389 | 1.0650 | 0.7832 | 0.070* | |
C4 | 1.0189 (2) | 0.97177 (17) | 0.69542 (16) | 0.0562 (4) | |
H4 | 1.0854 | 1.0201 | 0.7298 | 0.067* | |
C5 | 1.07461 (18) | 0.87266 (15) | 0.61254 (15) | 0.0464 (4) | |
C6 | 0.97310 (17) | 0.79982 (14) | 0.55904 (14) | 0.0416 (3) | |
C7 | 1.02802 (19) | 0.70018 (16) | 0.47545 (16) | 0.0515 (4) | |
H7 | 0.9625 | 0.6519 | 0.4398 | 0.062* | |
C8 | 1.1760 (2) | 0.67452 (19) | 0.44694 (18) | 0.0605 (5) | |
H8 | 1.2107 | 0.6085 | 0.3920 | 0.073* | |
C9 | 1.2771 (2) | 0.7456 (2) | 0.49869 (19) | 0.0633 (5) | |
H9 | 1.3782 | 0.7266 | 0.4781 | 0.076* | |
C10 | 1.2280 (2) | 0.84240 (19) | 0.57914 (18) | 0.0580 (5) | |
H10 | 1.2961 | 0.8895 | 0.6128 | 0.070* | |
C11 | 0.5602 (3) | 1.0473 (2) | 0.7849 (2) | 0.0859 (7) | |
H11A | 0.4542 | 1.0518 | 0.7914 | 0.129* | |
H11B | 0.5951 | 1.1311 | 0.7543 | 0.129* | |
H11C | 0.5912 | 1.0242 | 0.8678 | 0.129* | |
C12 | 0.12086 (16) | 0.31177 (13) | 0.90308 (14) | 0.0391 (3) | |
C13 | 0.19472 (16) | 0.40531 (14) | 0.82703 (14) | 0.0411 (3) | |
C14 | 0.11092 (19) | 0.51331 (15) | 0.77661 (15) | 0.0477 (4) | |
H14 | 0.1581 | 0.5779 | 0.7242 | 0.057* | |
C15 | −0.03834 (18) | 0.52299 (15) | 0.80456 (15) | 0.0483 (4) | |
H15 | −0.0915 | 0.5959 | 0.7721 | 0.058* | |
C16 | −0.11572 (17) | 0.42663 (14) | 0.88090 (14) | 0.0424 (3) | |
C17 | −0.03443 (16) | 0.31586 (14) | 0.93202 (14) | 0.0391 (3) | |
C18 | −0.11305 (19) | 0.22006 (16) | 1.00938 (17) | 0.0515 (4) | |
H18 | −0.0618 | 0.1475 | 1.0446 | 0.062* | |
C19 | −0.2632 (2) | 0.23339 (18) | 1.0326 (2) | 0.0612 (5) | |
H19 | −0.3135 | 0.1690 | 1.0827 | 0.073* | |
C20 | −0.34344 (19) | 0.34223 (19) | 0.9822 (2) | 0.0618 (5) | |
H20 | −0.4460 | 0.3497 | 0.9990 | 0.074* | |
C21 | −0.27129 (18) | 0.43676 (17) | 0.90895 (18) | 0.0532 (4) | |
H21 | −0.3251 | 0.5093 | 0.8767 | 0.064* | |
C22 | 0.4201 (2) | 0.47481 (19) | 0.71352 (18) | 0.0615 (5) | |
H22A | 0.5244 | 0.4516 | 0.7073 | 0.092* | |
H22B | 0.4010 | 0.5629 | 0.7403 | 0.092* | |
H22C | 0.3862 | 0.4688 | 0.6314 | 0.092* | |
N1 | 0.20980 (15) | 0.20198 (13) | 0.95773 (14) | 0.0483 (3) | |
N2 | 0.71338 (16) | 0.76148 (15) | 0.53852 (16) | 0.0571 (4) | |
O1 | 0.6734 (2) | 0.8025 (2) | 0.43824 (19) | 0.1118 (7) | |
O2 | 0.6708 (2) | 0.66298 (17) | 0.5941 (2) | 0.1043 (6) | |
O3 | 0.61970 (14) | 0.95078 (14) | 0.69777 (14) | 0.0703 (4) | |
O4 | 0.29054 (17) | 0.22522 (13) | 1.03577 (15) | 0.0785 (4) | |
O5 | 0.19774 (17) | 0.09259 (12) | 0.92409 (16) | 0.0767 (4) | |
O6 | 0.34371 (12) | 0.38730 (11) | 0.80514 (11) | 0.0537 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0446 (8) | 0.0428 (8) | 0.0464 (8) | −0.0077 (6) | −0.0072 (7) | 0.0025 (6) |
C2 | 0.0539 (10) | 0.0513 (9) | 0.0462 (9) | −0.0005 (7) | −0.0013 (7) | 0.0027 (7) |
C3 | 0.0772 (13) | 0.0527 (9) | 0.0447 (9) | −0.0034 (9) | −0.0046 (9) | −0.0084 (7) |
C4 | 0.0708 (12) | 0.0557 (10) | 0.0465 (9) | −0.0177 (8) | −0.0179 (8) | −0.0006 (7) |
C5 | 0.0510 (9) | 0.0486 (8) | 0.0410 (8) | −0.0110 (7) | −0.0117 (7) | 0.0069 (7) |
C6 | 0.0441 (8) | 0.0415 (7) | 0.0393 (8) | −0.0064 (6) | −0.0076 (6) | 0.0052 (6) |
C7 | 0.0527 (10) | 0.0499 (9) | 0.0526 (10) | −0.0041 (7) | −0.0081 (8) | −0.0046 (7) |
C8 | 0.0582 (11) | 0.0624 (11) | 0.0580 (11) | 0.0062 (8) | −0.0016 (8) | −0.0027 (8) |
C9 | 0.0455 (10) | 0.0768 (13) | 0.0640 (12) | 0.0008 (9) | −0.0028 (8) | 0.0118 (10) |
C10 | 0.0499 (10) | 0.0688 (11) | 0.0578 (11) | −0.0170 (8) | −0.0169 (8) | 0.0122 (9) |
C11 | 0.0839 (16) | 0.0823 (15) | 0.0800 (15) | 0.0233 (12) | 0.0198 (12) | −0.0064 (12) |
C12 | 0.0404 (8) | 0.0360 (7) | 0.0417 (8) | −0.0007 (6) | −0.0080 (6) | −0.0039 (6) |
C13 | 0.0390 (8) | 0.0445 (8) | 0.0403 (8) | −0.0033 (6) | −0.0047 (6) | −0.0046 (6) |
C14 | 0.0524 (9) | 0.0456 (8) | 0.0442 (8) | −0.0048 (7) | −0.0055 (7) | 0.0049 (6) |
C15 | 0.0522 (9) | 0.0444 (8) | 0.0483 (9) | 0.0032 (7) | −0.0121 (7) | 0.0036 (7) |
C16 | 0.0413 (8) | 0.0445 (8) | 0.0431 (8) | −0.0009 (6) | −0.0099 (6) | −0.0089 (6) |
C17 | 0.0392 (8) | 0.0386 (7) | 0.0409 (8) | −0.0042 (6) | −0.0070 (6) | −0.0069 (6) |
C18 | 0.0493 (9) | 0.0441 (8) | 0.0611 (10) | −0.0087 (7) | −0.0048 (8) | 0.0001 (7) |
C19 | 0.0505 (10) | 0.0582 (10) | 0.0746 (12) | −0.0188 (8) | 0.0041 (9) | −0.0067 (9) |
C20 | 0.0370 (9) | 0.0710 (12) | 0.0785 (13) | −0.0071 (8) | −0.0011 (8) | −0.0203 (10) |
C21 | 0.0411 (9) | 0.0570 (10) | 0.0636 (11) | 0.0021 (7) | −0.0125 (8) | −0.0125 (8) |
C22 | 0.0487 (10) | 0.0745 (12) | 0.0592 (11) | −0.0146 (9) | 0.0053 (8) | 0.0020 (9) |
N1 | 0.0435 (7) | 0.0412 (7) | 0.0595 (8) | −0.0011 (5) | −0.0071 (6) | 0.0016 (6) |
N2 | 0.0450 (8) | 0.0572 (9) | 0.0709 (10) | −0.0085 (6) | −0.0111 (7) | −0.0039 (7) |
O1 | 0.1262 (16) | 0.1253 (15) | 0.1010 (13) | −0.0526 (12) | −0.0681 (12) | 0.0190 (11) |
O2 | 0.1055 (13) | 0.0811 (11) | 0.1351 (16) | −0.0523 (10) | −0.0365 (11) | 0.0232 (10) |
O3 | 0.0542 (8) | 0.0768 (9) | 0.0753 (9) | 0.0099 (6) | 0.0049 (6) | −0.0104 (7) |
O4 | 0.0826 (10) | 0.0663 (8) | 0.0944 (11) | −0.0031 (7) | −0.0500 (9) | 0.0107 (7) |
O5 | 0.0839 (10) | 0.0403 (7) | 0.1082 (12) | 0.0091 (6) | −0.0230 (8) | −0.0139 (7) |
O6 | 0.0394 (6) | 0.0609 (7) | 0.0585 (7) | −0.0050 (5) | −0.0002 (5) | 0.0050 (5) |
C1—C2 | 1.372 (2) | C12—N1 | 1.4678 (19) |
C1—C6 | 1.411 (2) | C13—O6 | 1.3524 (18) |
C1—N2 | 1.466 (2) | C13—C14 | 1.412 (2) |
C2—O3 | 1.353 (2) | C14—C15 | 1.356 (2) |
C2—C3 | 1.404 (3) | C14—H14 | 0.9300 |
C3—C4 | 1.360 (3) | C15—C16 | 1.408 (2) |
C3—H3 | 0.9300 | C15—H15 | 0.9300 |
C4—C5 | 1.406 (2) | C16—C21 | 1.412 (2) |
C4—H4 | 0.9300 | C16—C17 | 1.423 (2) |
C5—C10 | 1.418 (2) | C17—C18 | 1.414 (2) |
C5—C6 | 1.419 (2) | C18—C19 | 1.361 (2) |
C6—C7 | 1.413 (2) | C18—H18 | 0.9300 |
C7—C8 | 1.358 (2) | C19—C20 | 1.400 (3) |
C7—H7 | 0.9300 | C19—H19 | 0.9300 |
C8—C9 | 1.396 (3) | C20—C21 | 1.357 (3) |
C8—H8 | 0.9300 | C20—H20 | 0.9300 |
C9—C10 | 1.360 (3) | C21—H21 | 0.9300 |
C9—H9 | 0.9300 | C22—O6 | 1.427 (2) |
C10—H10 | 0.9300 | C22—H22A | 0.9600 |
C11—O3 | 1.424 (2) | C22—H22B | 0.9600 |
C11—H11A | 0.9600 | C22—H22C | 0.9600 |
C11—H11B | 0.9600 | N1—O5 | 1.2129 (17) |
C11—H11C | 0.9600 | N1—O4 | 1.2136 (18) |
C12—C13 | 1.371 (2) | N2—O1 | 1.200 (2) |
C12—C17 | 1.411 (2) | N2—O2 | 1.200 (2) |
C2—C1—C6 | 124.01 (15) | O6—C13—C14 | 124.40 (14) |
C2—C1—N2 | 117.77 (15) | C12—C13—C14 | 118.16 (14) |
C6—C1—N2 | 118.21 (14) | C15—C14—C13 | 120.05 (14) |
O3—C2—C1 | 116.87 (16) | C15—C14—H14 | 120.0 |
O3—C2—C3 | 125.16 (16) | C13—C14—H14 | 120.0 |
C1—C2—C3 | 117.96 (16) | C14—C15—C16 | 122.34 (14) |
C4—C3—C2 | 120.12 (16) | C14—C15—H15 | 118.8 |
C4—C3—H3 | 119.9 | C16—C15—H15 | 118.8 |
C2—C3—H3 | 119.9 | C15—C16—C21 | 122.11 (14) |
C3—C4—C5 | 122.44 (16) | C15—C16—C17 | 118.92 (14) |
C3—C4—H4 | 118.8 | C21—C16—C17 | 118.97 (14) |
C5—C4—H4 | 118.8 | C12—C17—C18 | 124.80 (14) |
C4—C5—C10 | 123.00 (16) | C12—C17—C16 | 116.68 (13) |
C4—C5—C6 | 118.74 (15) | C18—C17—C16 | 118.51 (14) |
C10—C5—C6 | 118.27 (16) | C19—C18—C17 | 120.38 (16) |
C1—C6—C7 | 124.13 (14) | C19—C18—H18 | 119.8 |
C1—C6—C5 | 116.72 (14) | C17—C18—H18 | 119.8 |
C7—C6—C5 | 119.15 (15) | C18—C19—C20 | 121.21 (17) |
C8—C7—C6 | 120.33 (16) | C18—C19—H19 | 119.4 |
C8—C7—H7 | 119.8 | C20—C19—H19 | 119.4 |
C6—C7—H7 | 119.8 | C21—C20—C19 | 119.91 (16) |
C7—C8—C9 | 121.14 (18) | C21—C20—H20 | 120.0 |
C7—C8—H8 | 119.4 | C19—C20—H20 | 120.0 |
C9—C8—H8 | 119.4 | C20—C21—C16 | 121.01 (16) |
C10—C9—C8 | 120.03 (18) | C20—C21—H21 | 119.5 |
C10—C9—H9 | 120.0 | C16—C21—H21 | 119.5 |
C8—C9—H9 | 120.0 | O6—C22—H22A | 109.5 |
C9—C10—C5 | 121.09 (17) | O6—C22—H22B | 109.5 |
C9—C10—H10 | 119.5 | H22A—C22—H22B | 109.5 |
C5—C10—H10 | 119.5 | O6—C22—H22C | 109.5 |
O3—C11—H11A | 109.5 | H22A—C22—H22C | 109.5 |
O3—C11—H11B | 109.5 | H22B—C22—H22C | 109.5 |
H11A—C11—H11B | 109.5 | O5—N1—O4 | 123.26 (14) |
O3—C11—H11C | 109.5 | O5—N1—C12 | 118.58 (14) |
H11A—C11—H11C | 109.5 | O4—N1—C12 | 118.15 (13) |
H11B—C11—H11C | 109.5 | O1—N2—O2 | 122.74 (17) |
C13—C12—C17 | 123.81 (13) | O1—N2—C1 | 118.59 (15) |
C13—C12—N1 | 117.52 (13) | O2—N2—C1 | 118.65 (16) |
C17—C12—N1 | 118.66 (13) | C2—O3—C11 | 118.58 (17) |
O6—C13—C12 | 117.43 (13) | C13—O6—C22 | 117.88 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O5i | 0.93 | 2.57 | 3.409 (2) | 150 |
C11—H11A···O5ii | 0.96 | 2.60 | 3.462 (3) | 150 |
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O5i | 0.93 | 2.57 | 3.409 (2) | 150 |
C11—H11A···O5ii | 0.96 | 2.60 | 3.462 (3) | 150 |
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1, z. |
Acknowledgements
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.
References
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Govindarajan, M., Ganasan, K., Periandy, S. & Karabacak, M. (2011). Spectrochim. Acta A Mol. Biomol. Spectrosc. 79, 646–653. CrossRef CAS PubMed Google Scholar
Kirumakki, S. R., Nagaraju, N., Chary, K. V. R. & Narayanan, S. (2004). J. Catal. 221, 549–559. CrossRef CAS Google Scholar
Rokade, Y. B. & Sayyed, R. Z. (2009). Rasayan J. Chem. 2, 972–980 CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoylkova, T. Y., Chanev, C. D., Lechert, H. T. & Bezouhanova, C. P. (2000). Catal. Lett. 69, 109–112. CrossRef CAS Google Scholar
Upadhayaya, R. S., Vandavasi, J. K., Kardile, R. A., Lahore, S. V., Dixit, S. S., Deokar, H. S., Shinde, P. D., Sarmah, M. P. & Chattopadhyaya, J. (2010). Eur. J. Med. Chem. 45, 1854–1867. Web of Science CrossRef CAS PubMed Google Scholar
Wannalerse, B., Pannil, W., Loriang, J., Tuntulani, T. & Duangthongyou, T. (2013). Acta Cryst. E69, o682. CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wright, M. S., Lax, A. R., Henderson, G. & Chen, J. A. (2000). Mycologia, 92, 42–45. Web of Science CrossRef CAS Google Scholar
Yadav, G. D. & Krishnan, S. (1998). Ind. Eng. Chem. Res. 37, 3358–3365. CrossRef CAS Google Scholar
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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.