supplementary materials


lr2099 scheme

Acta Cryst. (2013). E69, o682    [ doi:10.1107/S1600536813008660 ]

2-Methoxy-1-(2-methoxy-4-nitronaphthalen-1-yl)-6-nitronaphthalene

B. Wannalerse, W. Pannil, J. Loriang, T. Tuntulani and T. Duangthongyou

Abstract top

In the title compound, C22H16N2O6, the naphthalene ring systems form a dihedral angle of 65.2 (1)°. Two O atoms of one of the nitro groups are disordered over two sets of sites with occupancy factors of 0.586 (15) and 0.414 (15). Weak C-H...O intermolecular interactions are present, forming a ladder like structure along the a axis.

Comment top

The molecule of the title compound, C22H16N2O6, contains two naphthalene rings forming a dihedral angle of 65.2 (1)° between them. The molecular structure is shown in Fig.1. The crystal structure is stabilized by weak C17—H17···O2 intermolecular interactions forming a ladder like structure, along the a axis (Fig. 2).

Related literature top

For related structures, see: Thorup et al. (2006, ); Thoss et al. (2009); Ge & Li (2009).

Experimental top

The (S)-2,2'-dimethoxy-1,1'-binaphthalene (0.5 g,1.98 mmol) was stirred in CH3CN(10 ml). Nitric acid (0.4 ml) in glacial acetic acid (5 ml) was added dropwise in 10 minutes. The mixture was then stirred at 70°C for 16 h after pouring into the water (50 ml) and extracted with dichloromethane (3x50 ml). The organic layer was washed with 1M KOH, brine and dried over Na2SO4. The mixture was filtrated and evaporated of the solvent afforded a yellow solid,then purified by column chromatography using dichloromethane: hexane = 7:3 as an eluent. Brown crystal were obtained from a mixture of dichloromethane:hexane.

Refinement top

All H atoms of the compound were placed in calculated positions with C—H = 0.93 Å (aromatic hydrogen) and 0.96 Å (methyl hydrogen) and included in the cycles of refinement using a riding model with Uiso(H) = 1.2 Ueq(C) and Uiso(H) = 1.5 Ueq(C) ,for aromatic and methyl hydrogens respectively. The resulting Flack's parameter value was meaningless and no absolute structure could be fixed and the Fiedel's pairs were merged in the last refinement.

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound (arbitrary spheres for the H atoms). Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing view of the compound (dash lines represent weak C—H···O interaction).
2-Methoxy-1-(2-methoxy-4-nitronaphthalen-1-yl)-6-nitronaphthalene top
Crystal data top
C22H16N2O6F(000) = 840
Mr = 404.37Dx = 1.400 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1608 reflections
a = 7.095 (16) Åθ = 2.7–18.9°
b = 15.14 (4) ŵ = 0.10 mm1
c = 17.86 (5) ÅT = 296 K
V = 1918 (9) Å3Bar, brown
Z = 40.36 × 0.16 × 0.14 mm
Data collection top
Bruker APEXII CCD
diffractometer
1440 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 24.8°, θmin = 2.9°
φ and ω scansh = 68
3043 measured reflectionsk = 017
1881 independent reflectionsl = 020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0534P)2 + 0.0581P]
where P = (Fo2 + 2Fc2)/3
1881 reflections(Δ/σ)max < 0.001
292 parametersΔρmax = 0.10 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C22H16N2O6V = 1918 (9) Å3
Mr = 404.37Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.095 (16) ŵ = 0.10 mm1
b = 15.14 (4) ÅT = 296 K
c = 17.86 (5) Å0.36 × 0.16 × 0.14 mm
Data collection top
Bruker APEXII CCD
diffractometer
1440 reflections with I > 2σ(I)
3043 measured reflectionsRint = 0.023
1881 independent reflectionsθmax = 24.8°
Refinement top
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.090Δρmax = 0.10 e Å3
S = 1.01Δρmin = 0.16 e Å3
1881 reflectionsAbsolute structure: ?
292 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.1345 (6)0.40153 (18)0.28224 (16)0.1209 (13)
O20.1746 (4)0.46589 (15)0.38886 (16)0.0921 (8)
O30.2362 (3)0.03073 (11)0.59542 (10)0.0567 (6)
O60.5329 (3)0.02923 (12)0.40128 (11)0.0520 (5)
N10.1607 (4)0.39888 (18)0.35029 (19)0.0688 (8)
N20.3170 (5)0.25427 (17)0.30186 (17)0.0626 (7)
C10.1670 (4)0.31102 (18)0.38691 (17)0.0480 (7)
C20.1735 (4)0.23483 (18)0.34021 (16)0.0515 (7)
H20.17020.24050.28840.062*
C30.1849 (4)0.15274 (19)0.37294 (15)0.0484 (7)
H30.18890.10280.34260.058*
C40.1908 (4)0.14237 (16)0.45239 (15)0.0393 (6)
C50.2108 (4)0.05732 (16)0.48721 (14)0.0405 (6)
C60.2104 (4)0.05224 (16)0.56536 (14)0.0437 (7)
C70.1857 (4)0.12987 (18)0.61018 (16)0.0496 (7)
H70.18170.12520.66210.059*
C80.1679 (4)0.21108 (18)0.57691 (15)0.0478 (7)
H80.15190.26080.60680.057*
C90.1735 (4)0.22098 (16)0.49791 (15)0.0411 (7)
C100.1630 (4)0.30550 (17)0.46272 (17)0.0474 (7)
H100.15340.35640.49160.057*
C110.2143 (6)0.0425 (2)0.67474 (16)0.0815 (11)
H11A0.09500.01880.69020.122*
H11B0.31400.01220.70050.122*
H11C0.21920.10430.68650.122*
C120.2779 (4)0.17661 (17)0.35106 (14)0.0447 (7)
C130.1069 (4)0.17088 (17)0.39423 (15)0.0442 (7)
C140.0412 (4)0.23552 (19)0.39645 (17)0.0565 (8)
H140.03130.28610.36720.068*
C150.1982 (5)0.2240 (2)0.44130 (18)0.0622 (9)
H150.29070.26750.44280.075*
C160.2194 (5)0.1468 (2)0.48479 (17)0.0606 (8)
H160.32670.13900.51400.073*
C170.0808 (4)0.08277 (19)0.48406 (15)0.0493 (7)
H170.09690.03220.51290.059*
C180.0887 (4)0.09202 (16)0.43966 (15)0.0410 (6)
C190.2341 (4)0.02545 (16)0.44096 (13)0.0396 (6)
C200.3965 (4)0.03611 (16)0.39655 (15)0.0414 (6)
C210.4176 (4)0.11250 (16)0.35163 (15)0.0445 (7)
H210.52520.11970.32250.053*
C220.6813 (4)0.0311 (2)0.34571 (16)0.0582 (8)
H22A0.62680.03730.29680.087*
H22B0.75210.02280.34810.087*
H22C0.76340.08020.35540.087*
O4A0.448 (2)0.2544 (8)0.2597 (5)0.093 (3)0.586 (15)
O5A0.1822 (7)0.2895 (6)0.2681 (5)0.099 (4)0.586 (15)
O4B0.479 (2)0.2756 (12)0.2933 (11)0.098 (5)0.414 (15)
O5B0.250 (2)0.3295 (4)0.3232 (8)0.114 (6)0.414 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.222 (4)0.0738 (17)0.0670 (17)0.010 (2)0.024 (2)0.0264 (15)
O20.118 (2)0.0473 (14)0.111 (2)0.0124 (14)0.0229 (18)0.0075 (15)
O30.0807 (14)0.0467 (11)0.0425 (10)0.0087 (11)0.0065 (11)0.0015 (10)
O60.0450 (10)0.0511 (11)0.0599 (12)0.0070 (9)0.0132 (10)0.0137 (11)
N10.0765 (19)0.0542 (17)0.076 (2)0.0037 (15)0.0094 (17)0.0106 (17)
N20.078 (2)0.0498 (17)0.0600 (19)0.0029 (17)0.0004 (18)0.0139 (15)
C10.0424 (15)0.0427 (15)0.059 (2)0.0005 (14)0.0053 (14)0.0083 (14)
C20.0532 (17)0.0575 (18)0.0437 (17)0.0017 (16)0.0024 (14)0.0016 (16)
C30.0540 (18)0.0464 (16)0.0449 (16)0.0049 (16)0.0043 (15)0.0033 (13)
C40.0341 (14)0.0427 (15)0.0411 (15)0.0013 (13)0.0030 (12)0.0026 (13)
C50.0412 (15)0.0388 (14)0.0414 (14)0.0023 (13)0.0053 (12)0.0060 (12)
C60.0462 (16)0.0440 (15)0.0409 (15)0.0012 (14)0.0035 (13)0.0002 (13)
C70.0568 (17)0.0544 (18)0.0375 (16)0.0021 (15)0.0052 (15)0.0068 (14)
C80.0513 (16)0.0459 (16)0.0462 (17)0.0036 (14)0.0055 (14)0.0123 (14)
C90.0368 (14)0.0408 (14)0.0457 (16)0.0006 (14)0.0026 (12)0.0035 (13)
C100.0407 (15)0.0413 (15)0.0601 (19)0.0005 (13)0.0069 (14)0.0085 (15)
C110.136 (3)0.0622 (19)0.0467 (18)0.007 (2)0.020 (2)0.0107 (16)
C120.0596 (18)0.0376 (14)0.0368 (14)0.0100 (15)0.0055 (14)0.0056 (13)
C130.0510 (16)0.0395 (14)0.0420 (16)0.0047 (14)0.0071 (13)0.0053 (14)
C140.069 (2)0.0482 (16)0.053 (2)0.0082 (16)0.0136 (17)0.0005 (16)
C150.063 (2)0.0585 (19)0.065 (2)0.0234 (18)0.0104 (18)0.0144 (17)
C160.0518 (19)0.072 (2)0.0583 (19)0.0074 (18)0.0034 (16)0.0146 (18)
C170.0500 (16)0.0501 (15)0.0479 (17)0.0034 (16)0.0036 (14)0.0059 (15)
C180.0470 (15)0.0383 (14)0.0376 (14)0.0025 (14)0.0040 (13)0.0072 (13)
C190.0446 (15)0.0393 (14)0.0349 (14)0.0036 (13)0.0002 (13)0.0014 (12)
C200.0461 (15)0.0379 (14)0.0403 (15)0.0036 (13)0.0008 (13)0.0042 (14)
C210.0471 (16)0.0456 (15)0.0408 (16)0.0078 (14)0.0020 (13)0.0045 (14)
C220.0557 (18)0.0656 (19)0.0532 (17)0.0046 (17)0.0131 (16)0.0008 (17)
O4A0.132 (9)0.072 (5)0.075 (5)0.014 (5)0.053 (6)0.031 (4)
O5A0.085 (3)0.096 (6)0.117 (7)0.003 (3)0.020 (3)0.061 (5)
O4B0.073 (5)0.095 (10)0.125 (13)0.021 (6)0.005 (8)0.052 (9)
O5B0.194 (12)0.035 (4)0.112 (9)0.022 (5)0.071 (9)0.015 (4)
Geometric parameters (Å, º) top
O1—N11.230 (5)C8—H80.9300
O2—N11.230 (4)C9—C101.428 (5)
O3—C61.378 (4)C10—H100.9300
O3—C111.436 (5)C11—H11A0.9600
O6—C201.386 (4)C11—H11B0.9600
O6—C221.447 (4)C11—H11C0.9600
N1—C11.483 (5)C12—C211.387 (5)
N2—O4A1.193 (12)C12—C131.440 (5)
N2—O4B1.206 (17)C13—C141.436 (5)
N2—O5A1.250 (5)C13—C181.449 (5)
N2—O5B1.292 (7)C14—C151.383 (5)
N2—C121.494 (4)C14—H140.9300
C1—C101.357 (5)C15—C161.412 (5)
C1—C21.424 (5)C15—H150.9300
C2—C31.376 (5)C16—C171.381 (5)
C2—H20.9300C16—H160.9300
C3—C41.428 (5)C17—C181.448 (5)
C3—H30.9300C17—H170.9300
C4—C51.437 (5)C18—C191.442 (4)
C4—C91.447 (5)C19—C201.408 (4)
C5—C61.398 (5)C20—C211.416 (4)
C5—C191.510 (5)C21—H210.9300
C6—C71.433 (5)C22—H22A0.9600
C7—C81.371 (5)C22—H22B0.9600
C7—H70.9300C22—H22C0.9600
C8—C91.419 (5)
C6—O3—C11118.9 (2)C9—C10—H10120.2
C20—O6—C22118.7 (2)O3—C11—H11A109.5
O1—N1—O2122.6 (3)O3—C11—H11B109.5
O1—N1—C1118.0 (3)H11A—C11—H11B109.5
O2—N1—C1119.4 (3)O3—C11—H11C109.5
O4A—N2—O4B34.8 (7)H11A—C11—H11C109.5
O4A—N2—O5A106.8 (8)H11B—C11—H11C109.5
O4B—N2—O5A123.8 (9)C21—C12—C13123.8 (3)
O4A—N2—O5B118.1 (8)C21—C12—N2115.0 (3)
O4B—N2—O5B98.9 (13)C13—C12—N2121.3 (3)
O5A—N2—O5B58.9 (5)C14—C13—C12126.2 (3)
O4A—N2—C12121.1 (6)C14—C13—C18118.7 (3)
O4B—N2—C12117.6 (8)C12—C13—C18115.1 (2)
O5A—N2—C12118.5 (4)C15—C14—C13121.3 (3)
O5B—N2—C12116.9 (4)C15—C14—H14119.4
C10—C1—C2122.4 (3)C13—C14—H14119.4
C10—C1—N1119.6 (3)C14—C15—C16120.6 (3)
C2—C1—N1118.0 (3)C14—C15—H15119.7
C3—C2—C1119.0 (3)C16—C15—H15119.7
C3—C2—H2120.5C17—C16—C15120.0 (3)
C1—C2—H2120.5C17—C16—H16120.0
C2—C3—C4121.6 (3)C15—C16—H16120.0
C2—C3—H3119.2C16—C17—C18121.9 (3)
C4—C3—H3119.2C16—C17—H17119.0
C3—C4—C5122.1 (2)C18—C17—H17119.0
C3—C4—C9117.7 (3)C19—C18—C17121.2 (3)
C5—C4—C9120.2 (3)C19—C18—C13121.4 (3)
C6—C5—C4118.8 (2)C17—C18—C13117.4 (2)
C6—C5—C19120.0 (2)C20—C19—C18119.7 (3)
C4—C5—C19121.2 (3)C20—C19—C5119.5 (2)
O3—C6—C5116.0 (2)C18—C19—C5120.7 (2)
O3—C6—C7123.1 (3)O6—C20—C19117.1 (2)
C5—C6—C7120.9 (3)O6—C20—C21122.9 (3)
C8—C7—C6120.3 (3)C19—C20—C21120.0 (2)
C8—C7—H7119.8C12—C21—C20120.0 (3)
C6—C7—H7119.8C12—C21—H21120.0
C7—C8—C9121.5 (2)C20—C21—H21120.0
C7—C8—H8119.2O6—C22—H22A109.5
C9—C8—H8119.2O6—C22—H22B109.5
C8—C9—C10122.1 (2)H22A—C22—H22B109.5
C8—C9—C4118.3 (3)O6—C22—H22C109.5
C10—C9—C4119.6 (3)H22A—C22—H22C109.5
C1—C10—C9119.6 (3)H22B—C22—H22C109.5
C1—C10—H10120.2
O1—N1—C1—C10168.7 (3)O4B—N2—C12—C13148.8 (11)
O2—N1—C1—C108.6 (5)O5A—N2—C12—C1336.0 (7)
O1—N1—C1—C210.1 (5)O5B—N2—C12—C1331.5 (11)
O2—N1—C1—C2172.6 (3)C21—C12—C13—C14179.3 (3)
C10—C1—C2—C33.1 (4)N2—C12—C13—C140.5 (4)
N1—C1—C2—C3178.2 (3)C21—C12—C13—C180.0 (4)
C1—C2—C3—C40.2 (4)N2—C12—C13—C18179.7 (2)
C2—C3—C4—C5177.3 (3)C12—C13—C14—C15178.6 (3)
C2—C3—C4—C93.5 (4)C18—C13—C14—C150.6 (4)
C3—C4—C5—C6178.3 (3)C13—C14—C15—C161.7 (4)
C9—C4—C5—C60.9 (4)C14—C15—C16—C171.4 (5)
C3—C4—C5—C192.3 (4)C15—C16—C17—C180.1 (4)
C9—C4—C5—C19178.4 (2)C16—C17—C18—C19178.5 (3)
C11—O3—C6—C5172.4 (3)C16—C17—C18—C131.2 (4)
C11—O3—C6—C78.0 (4)C14—C13—C18—C19178.8 (2)
C4—C5—C6—O3178.0 (2)C12—C13—C18—C190.5 (3)
C19—C5—C6—O31.4 (4)C14—C13—C18—C170.9 (3)
C4—C5—C6—C71.6 (4)C12—C13—C18—C17179.8 (2)
C19—C5—C6—C7179.1 (2)C17—C18—C19—C20179.4 (2)
O3—C6—C7—C8177.5 (3)C13—C18—C19—C200.9 (4)
C5—C6—C7—C82.1 (4)C17—C18—C19—C51.8 (4)
C6—C7—C8—C90.0 (5)C13—C18—C19—C5178.6 (2)
C7—C8—C9—C10177.4 (3)C6—C5—C19—C20114.4 (3)
C7—C8—C9—C42.5 (4)C4—C5—C19—C2064.9 (3)
C3—C4—C9—C8176.4 (2)C6—C5—C19—C1868.0 (3)
C5—C4—C9—C82.9 (4)C4—C5—C19—C18112.7 (3)
C3—C4—C9—C103.8 (4)C22—O6—C20—C19166.9 (2)
C5—C4—C9—C10176.9 (3)C22—O6—C20—C2115.2 (4)
C2—C1—C10—C92.7 (5)C18—C19—C20—O6178.8 (2)
N1—C1—C10—C9178.5 (2)C5—C19—C20—O63.5 (3)
C8—C9—C10—C1179.3 (3)C18—C19—C20—C210.8 (4)
C4—C9—C10—C10.8 (4)C5—C19—C20—C21178.5 (2)
O4A—N2—C12—C219.0 (9)C13—C12—C21—C200.1 (4)
O4B—N2—C12—C2130.9 (12)N2—C12—C21—C20179.6 (2)
O5A—N2—C12—C21144.3 (7)O6—C20—C21—C12178.2 (2)
O5B—N2—C12—C21148.3 (10)C19—C20—C21—C120.3 (4)
O4A—N2—C12—C13171.3 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17···O2i0.932.593.361 (10)140
Symmetry code: (i) x1/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17···O2i0.932.593.361 (10)140
Symmetry code: (i) x1/2, y+1/2, z+1.
Acknowledgements top

The authors thank the Thailand Research Fund (MRG 5580182) and the Center of Excellence for Innovation in Chemistry (PERCH–CIC), Commission on Education, Ministry of Education, for financial support.

references
References top

Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Ge, J.-Z. & Li, H. (2009). Acta Cryst. E65, o1179.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Thorup, N., Deussen, H.-J., Bechgaard, K. & Bjørnholm, T. (2006). Acta Cryst. E62, o1342–o1343.

Thoss, M., Seidel, R. W. & Feigel, M. (2009). Acta Cryst. E65, o243.