1,8-Bis(4-meth-oxy-3-nitro-phen-yl)naphthalene.

Mol-ecules of the title compound, C(24)H(18)N(2)O(6), are located on a twofold rotation axis passing through through the central C-C bond of the naphthalene ring system. The mol-ecular conformation is characterized by a roughly coplanar arrangement of the two substituted phenyl rings [dihedral angle 18.53 (5)°]. These two aryl rings are each twisted by 65.40 (5)° from the plane of the naphthyl unit.

Related literature

For use of the title compound as a building block for the synthesis of multidentate ligands, see: Sabater et al. (2005 ▶); Baruah et al. (2007 ▶); Prabhakaran et al. (2009 ▶). For the synthesis of the title compound, see: Letsinger et al. (1965 ▶); Li et al. (2005 ▶).

Experimental

Crystal data

C24H18N2O6

M = 430.40

Tetragonal,

a = 13.3038 (9) Å

c = 22.7868 (11) Å

V = 4033.1 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.35 × 0.24 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.965, T max = 0.988

9753 measured reflections

959 independent reflections

918 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.088

S = 1.07

959 reflections

156 parameters

1 restraint

Only H-atom displacement parameters refined

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: pyMOL (DeLano, 2004 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811036567/bt5623sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036567/bt5623Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036567/bt5623Isup3.cml

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

C24H18N2O6	Dx = 1.418 Mg m−3
Mr = 430.40	Melting point: 494 K
Tetragonal, I41cd	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I 4bw -2c	Cell parameters from 4285 reflections
a = 13.3038 (9) Å	θ = 2.8–27.5°
c = 22.7868 (11) Å	µ = 0.10 mm−1
V = 4033.1 (6) Å3	T = 293 K
Z = 8	Needle, yellow
F(000) = 1792	0.35 × 0.24 × 0.12 mm

Bruker SMART CCD area-detector diffractometer	959 independent reflections
Radiation source: fine-focus sealed tube	918 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω Scan scans	θmax = 25.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −12→16
Tmin = 0.965, Tmax = 0.988	k = −16→14
9753 measured reflections	l = −25→27

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	Only H-atom displacement parameters refined
S = 1.07	w = 1/[σ2(Fo2) + (0.0507P)2 + 0.8056P] where P = (Fo2 + 2Fc2)/3
959 reflections	(Δ/σ)max = 0.001
156 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.20 e Å−3

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.

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 > σ(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.

	x	y	z	Uiso*/Ueq
N1	0.82311 (12)	0.58354 (11)	0.35152 (7)	0.0469 (4)
O2	0.76244 (14)	0.63612 (12)	0.32705 (7)	0.0833 (6)
O3	0.85433 (18)	0.60222 (14)	0.40005 (7)	0.0931 (7)
O4	0.86899 (11)	0.40341 (10)	0.40686 (6)	0.0546 (4)
C1	0.92726 (13)	0.43673 (14)	0.16094 (8)	0.0426 (4)
C2	0.86451 (15)	0.37792 (16)	0.12783 (10)	0.0533 (5)
H2	0.8188	0.3365	0.1470	0.057 (6)*
C3	0.86637 (18)	0.37761 (19)	0.06630 (10)	0.0624 (6)
H3	0.8232	0.3362	0.0452	0.054 (6)*
C4	1.06781 (17)	0.56135 (18)	0.03803 (9)	0.0603 (6)
H4	1.0675	0.5600	−0.0028	0.052 (6)*
C5	1.0000	0.5000	0.06919 (11)	0.0483 (6)
C6	1.0000	0.5000	0.13242 (11)	0.0416 (5)
C7	0.91362 (12)	0.42884 (13)	0.22606 (7)	0.0398 (4)
C8	0.87701 (11)	0.50813 (12)	0.25959 (7)	0.0373 (4)
H8	0.8617	0.5689	0.2416	0.033 (4)*
C9	0.86311 (12)	0.49760 (12)	0.31946 (7)	0.0384 (4)
C10	0.88427 (12)	0.40744 (13)	0.34828 (8)	0.0417 (4)
C11	0.91814 (14)	0.32758 (13)	0.31419 (9)	0.0460 (4)
H11	0.9317	0.2660	0.3318	0.056 (5)*
C12	0.93181 (13)	0.33873 (14)	0.25471 (8)	0.0455 (4)
H12	0.9540	0.2839	0.2330	0.042 (5)*
C13	0.89059 (19)	0.31077 (18)	0.43594 (9)	0.0624 (6)
H13A	0.8490	0.2585	0.4200	0.069 (7)*
H13B	0.8772	0.3177	0.4771	0.083 (8)*
H13C	0.9601	0.2938	0.4302	0.067 (6)*

	U11	U22	U33	U12	U13	U23
N1	0.0583 (9)	0.0482 (8)	0.0342 (8)	0.0077 (7)	−0.0010 (7)	0.0013 (6)
O2	0.1003 (13)	0.0813 (11)	0.0682 (11)	0.0486 (10)	−0.0270 (10)	−0.0212 (9)
O3	0.1602 (18)	0.0772 (12)	0.0417 (10)	0.0396 (12)	−0.0298 (11)	−0.0138 (8)
O4	0.0720 (9)	0.0572 (8)	0.0347 (7)	0.0103 (6)	0.0072 (6)	0.0128 (6)
C1	0.0463 (9)	0.0471 (9)	0.0345 (9)	0.0074 (7)	−0.0020 (7)	−0.0019 (7)
C2	0.0553 (11)	0.0579 (12)	0.0467 (10)	0.0007 (9)	−0.0051 (10)	−0.0060 (9)
C3	0.0673 (13)	0.0728 (14)	0.0470 (12)	0.0058 (10)	−0.0176 (11)	−0.0178 (10)
C4	0.0719 (13)	0.0799 (15)	0.0292 (9)	0.0164 (12)	0.0086 (9)	0.0108 (10)
C5	0.0563 (15)	0.0583 (15)	0.0305 (14)	0.0153 (11)	0.000	0.000
C6	0.0476 (13)	0.0499 (13)	0.0274 (11)	0.0130 (11)	0.000	0.000
C7	0.0386 (8)	0.0464 (10)	0.0343 (9)	−0.0015 (7)	−0.0013 (7)	0.0012 (7)
C8	0.0370 (8)	0.0414 (8)	0.0335 (8)	0.0013 (6)	−0.0048 (7)	0.0050 (7)
C9	0.0377 (8)	0.0433 (9)	0.0342 (9)	0.0009 (6)	−0.0013 (7)	−0.0010 (7)
C10	0.0416 (9)	0.0457 (9)	0.0380 (9)	0.0016 (7)	0.0002 (8)	0.0064 (7)
C11	0.0541 (10)	0.0381 (9)	0.0457 (11)	0.0020 (7)	0.0009 (8)	0.0097 (7)
C12	0.0506 (10)	0.0417 (9)	0.0442 (10)	0.0015 (7)	0.0005 (8)	−0.0036 (8)
C13	0.0770 (15)	0.0650 (13)	0.0452 (13)	0.0061 (11)	0.0006 (10)	0.0205 (10)

N1—O2	1.205 (2)	C5—C4i	1.409 (3)
N1—O3	1.207 (2)	C5—C6	1.441 (3)
N1—C9	1.457 (2)	C6—C1i	1.438 (2)
O4—C10	1.351 (2)	C7—C12	1.386 (3)
O4—C13	1.428 (3)	C7—C8	1.390 (2)
C1—C2	1.371 (3)	C8—C9	1.384 (2)
C1—C6	1.438 (2)	C8—H8	0.9300
C1—C7	1.499 (2)	C9—C10	1.396 (2)
C2—C3	1.402 (3)	C10—C11	1.391 (3)
C2—H2	0.9300	C11—C12	1.376 (3)
C3—C4i	1.357 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—H12	0.9300
C4—C3i	1.357 (3)	C13—H13A	0.9600
C4—C5	1.409 (3)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
O2—N1—O3	122.34 (16)	C12—C7—C1	120.37 (16)
O2—N1—C9	117.92 (15)	C8—C7—C1	122.23 (15)
O3—N1—C9	119.67 (16)	C9—C8—C7	120.78 (15)
C10—O4—C13	117.53 (15)	C9—C8—H8	119.6
C2—C1—C6	119.70 (18)	C7—C8—H8	119.6
C2—C1—C7	115.55 (17)	C8—C9—C10	121.58 (15)
C6—C1—C7	124.75 (16)	C8—C9—N1	117.62 (14)
C1—C2—C3	122.8 (2)	C10—C9—N1	120.79 (15)
C1—C2—H2	118.6	O4—C10—C11	124.76 (15)
C3—C2—H2	118.6	O4—C10—C9	117.93 (15)
C4i—C3—C2	119.0 (2)	C11—C10—C9	117.31 (16)
C4i—C3—H3	120.5	C12—C11—C10	120.71 (17)
C2—C3—H3	120.5	C12—C11—H11	119.6
C3i—C4—C5	121.4 (2)	C10—C11—H11	119.6
C3i—C4—H4	119.3	C11—C12—C7	122.28 (17)
C5—C4—H4	119.3	C11—C12—H12	118.9
C4—C5—C4i	119.5 (3)	C7—C12—H12	118.9
C4—C5—C6	120.27 (13)	O4—C13—H13A	109.5
C4i—C5—C6	120.27 (13)	O4—C13—H13B	109.5
C1i—C6—C1	126.3 (2)	H13A—C13—H13B	109.5
C1i—C6—C5	116.87 (11)	O4—C13—H13C	109.5
C1—C6—C5	116.87 (11)	H13A—C13—H13C	109.5
C12—C7—C8	117.29 (15)	H13B—C13—H13C	109.5
C6—C1—C2—C3	−1.2 (3)	C1—C7—C8—C9	178.49 (14)
C7—C1—C2—C3	178.96 (19)	C7—C8—C9—C10	−0.6 (2)
C1—C2—C3—C4i	−0.7 (3)	C7—C8—C9—N1	−179.13 (15)
C3i—C4—C5—C4i	179.3 (2)	O2—N1—C9—C8	34.9 (2)
C3i—C4—C5—C6	−0.7 (2)	O3—N1—C9—C8	−142.0 (2)
C2—C1—C6—C1i	−177.96 (18)	O2—N1—C9—C10	−143.71 (18)
C7—C1—C6—C1i	1.86 (12)	O3—N1—C9—C10	39.4 (3)
C2—C1—C6—C5	2.04 (18)	C13—O4—C10—C11	0.9 (3)
C7—C1—C6—C5	−178.14 (12)	C13—O4—C10—C9	179.84 (18)
C4—C5—C6—C1i	−1.12 (13)	C8—C9—C10—O4	179.78 (15)
C4i—C5—C6—C1i	178.88 (13)	N1—C9—C10—O4	−1.7 (2)
C4—C5—C6—C1	178.88 (13)	C8—C9—C10—C11	−1.2 (2)
C4i—C5—C6—C1	−1.12 (13)	N1—C9—C10—C11	177.28 (16)
C2—C1—C7—C12	63.6 (2)	O4—C10—C11—C12	−179.82 (18)
C6—C1—C7—C12	−116.24 (17)	C9—C10—C11—C12	1.3 (3)
C2—C1—C7—C8	−112.50 (19)	C10—C11—C12—C7	0.5 (3)
C6—C1—C7—C8	67.7 (2)	C8—C7—C12—C11	−2.3 (3)
C12—C7—C8—C9	2.3 (2)	C1—C7—C12—C11	−178.55 (17)