2-Meth-oxy-1-(2-meth-oxy-4-nitro-naphthalen-1-yl)-6-nitro-naphthalene.

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 inter-molecular inter-actions are present, forming a ladder like structure along the a axis.

Related literature

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

Experimental

Crystal data

C22H16N2O6

M = 404.37

Orthorhombic,

a = 7.095 (16) Å

b = 15.14 (4) Å

c = 17.86 (5) Å

V = 1918 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.36 × 0.16 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer

3043 measured reflections

1881 independent reflections

1440 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.090

S = 1.01

1881 reflections

292 parameters

H-atom parameters constrained

Δρmax = 0.10 e Å−3

Δρmin = −0.16 e Å−3

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

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813008660/lr2099sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008660/lr2099Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008660/lr2099Isup3.cml

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

C22H16N2O6	F(000) = 840
Mr = 404.37	Dx = 1.400 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1608 reflections
a = 7.095 (16) Å	θ = 2.7–18.9°
b = 15.14 (4) Å	µ = 0.10 mm−1
c = 17.86 (5) Å	T = 296 K
V = 1918 (9) Å3	Bar, brown
Z = 4	0.36 × 0.16 × 0.14 mm

Bruker APEXII CCD diffractometer	1440 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 24.8°, θmin = 2.9°
φ and ω scans	h = −6→8
3043 measured reflections	k = 0→17
1881 independent reflections	l = 0→20

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) = 0.090	H-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 parameters	Δρmax = 0.10 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.1345 (6)	0.40153 (18)	0.28224 (16)	0.1209 (13)
O2	0.1746 (4)	0.46589 (15)	0.38886 (16)	0.0921 (8)
O3	0.2362 (3)	−0.03073 (11)	0.59542 (10)	0.0567 (6)
O6	0.5329 (3)	0.02923 (12)	0.40128 (11)	0.0520 (5)
N1	0.1607 (4)	0.39888 (18)	0.35029 (19)	0.0688 (8)
N2	0.3170 (5)	−0.25427 (17)	0.30186 (17)	0.0626 (7)
C1	0.1670 (4)	0.31102 (18)	0.38691 (17)	0.0480 (7)
C2	0.1735 (4)	0.23483 (18)	0.34021 (16)	0.0515 (7)
H2	0.1702	0.2405	0.2884	0.062*
C3	0.1849 (4)	0.15274 (19)	0.37294 (15)	0.0484 (7)
H3	0.1889	0.1028	0.3426	0.058*
C4	0.1908 (4)	0.14237 (16)	0.45239 (15)	0.0393 (6)
C5	0.2108 (4)	0.05732 (16)	0.48721 (14)	0.0405 (6)
C6	0.2104 (4)	0.05224 (16)	0.56536 (14)	0.0437 (7)
C7	0.1857 (4)	0.12987 (18)	0.61018 (16)	0.0496 (7)
H7	0.1817	0.1252	0.6621	0.059*
C8	0.1679 (4)	0.21108 (18)	0.57691 (15)	0.0478 (7)
H8	0.1519	0.2608	0.6068	0.057*
C9	0.1735 (4)	0.22098 (16)	0.49791 (15)	0.0411 (7)
C10	0.1630 (4)	0.30550 (17)	0.46272 (17)	0.0474 (7)
H10	0.1534	0.3564	0.4916	0.057*
C11	0.2143 (6)	−0.0425 (2)	0.67474 (16)	0.0815 (11)
H11A	0.0950	−0.0188	0.6902	0.122*
H11B	0.3140	−0.0122	0.7005	0.122*
H11C	0.2192	−0.1043	0.6865	0.122*
C12	0.2779 (4)	−0.17661 (17)	0.35106 (14)	0.0447 (7)
C13	0.1069 (4)	−0.17088 (17)	0.39423 (15)	0.0442 (7)
C14	−0.0412 (4)	−0.23552 (19)	0.39645 (17)	0.0565 (8)
H14	−0.0313	−0.2861	0.3672	0.068*
C15	−0.1982 (5)	−0.2240 (2)	0.44130 (18)	0.0622 (9)
H15	−0.2907	−0.2675	0.4428	0.075*
C16	−0.2194 (5)	−0.1468 (2)	0.48479 (17)	0.0606 (8)
H16	−0.3267	−0.1390	0.5140	0.073*
C17	−0.0808 (4)	−0.08277 (19)	0.48406 (15)	0.0493 (7)
H17	−0.0969	−0.0322	0.5129	0.059*
C18	0.0887 (4)	−0.09202 (16)	0.43966 (15)	0.0410 (6)
C19	0.2341 (4)	−0.02545 (16)	0.44096 (13)	0.0396 (6)
C20	0.3965 (4)	−0.03611 (16)	0.39655 (15)	0.0414 (6)
C21	0.4176 (4)	−0.11250 (16)	0.35163 (15)	0.0445 (7)
H21	0.5252	−0.1197	0.3225	0.053*
C22	0.6813 (4)	0.0311 (2)	0.34571 (16)	0.0582 (8)
H22A	0.6268	0.0373	0.2968	0.087*
H22B	0.7521	−0.0228	0.3481	0.087*
H22C	0.7634	0.0802	0.3554	0.087*
O4A	0.448 (2)	−0.2544 (8)	0.2597 (5)	0.093 (3)	0.586 (15)
O5A	0.1822 (7)	−0.2895 (6)	0.2681 (5)	0.099 (4)	0.586 (15)
O4B	0.479 (2)	−0.2756 (12)	0.2933 (11)	0.098 (5)	0.414 (15)
O5B	0.250 (2)	−0.3295 (4)	0.3232 (8)	0.114 (6)	0.414 (15)

	U11	U22	U33	U12	U13	U23
O1	0.222 (4)	0.0738 (17)	0.0670 (17)	0.010 (2)	0.024 (2)	0.0264 (15)
O2	0.118 (2)	0.0473 (14)	0.111 (2)	−0.0124 (14)	−0.0229 (18)	0.0075 (15)
O3	0.0807 (14)	0.0467 (11)	0.0425 (10)	0.0087 (11)	0.0065 (11)	0.0015 (10)
O6	0.0450 (10)	0.0511 (11)	0.0599 (12)	−0.0070 (9)	0.0132 (10)	−0.0137 (11)
N1	0.0765 (19)	0.0542 (17)	0.076 (2)	−0.0037 (15)	0.0094 (17)	0.0106 (17)
N2	0.078 (2)	0.0498 (17)	0.0600 (19)	0.0029 (17)	−0.0004 (18)	−0.0139 (15)
C1	0.0424 (15)	0.0427 (15)	0.059 (2)	0.0005 (14)	0.0053 (14)	0.0083 (14)
C2	0.0532 (17)	0.0575 (18)	0.0437 (17)	0.0017 (16)	0.0024 (14)	0.0016 (16)
C3	0.0540 (18)	0.0464 (16)	0.0449 (16)	0.0049 (16)	0.0043 (15)	−0.0033 (13)
C4	0.0341 (14)	0.0427 (15)	0.0411 (15)	0.0013 (13)	0.0030 (12)	−0.0026 (13)
C5	0.0412 (15)	0.0388 (14)	0.0414 (14)	0.0023 (13)	0.0053 (12)	−0.0060 (12)
C6	0.0462 (16)	0.0440 (15)	0.0409 (15)	0.0012 (14)	0.0035 (13)	−0.0002 (13)
C7	0.0568 (17)	0.0544 (18)	0.0375 (16)	0.0021 (15)	0.0052 (15)	−0.0068 (14)
C8	0.0513 (16)	0.0459 (16)	0.0462 (17)	0.0036 (14)	0.0055 (14)	−0.0123 (14)
C9	0.0368 (14)	0.0408 (14)	0.0457 (16)	0.0006 (14)	0.0026 (12)	−0.0035 (13)
C10	0.0407 (15)	0.0413 (15)	0.0601 (19)	0.0005 (13)	0.0069 (14)	−0.0085 (15)
C11	0.136 (3)	0.0622 (19)	0.0467 (18)	0.007 (2)	0.020 (2)	0.0107 (16)
C12	0.0596 (18)	0.0376 (14)	0.0368 (14)	0.0100 (15)	−0.0055 (14)	−0.0056 (13)
C13	0.0510 (16)	0.0395 (14)	0.0420 (16)	0.0047 (14)	−0.0071 (13)	0.0053 (14)
C14	0.069 (2)	0.0482 (16)	0.053 (2)	−0.0082 (16)	−0.0136 (17)	0.0005 (16)
C15	0.063 (2)	0.0585 (19)	0.065 (2)	−0.0234 (18)	−0.0104 (18)	0.0144 (17)
C16	0.0518 (19)	0.072 (2)	0.0583 (19)	−0.0074 (18)	0.0034 (16)	0.0146 (18)
C17	0.0500 (16)	0.0501 (15)	0.0479 (17)	0.0034 (16)	0.0036 (14)	0.0059 (15)
C18	0.0470 (15)	0.0383 (14)	0.0376 (14)	0.0025 (14)	−0.0040 (13)	0.0072 (13)
C19	0.0446 (15)	0.0393 (14)	0.0349 (14)	0.0036 (13)	0.0002 (13)	0.0014 (12)
C20	0.0461 (15)	0.0379 (14)	0.0403 (15)	0.0036 (13)	−0.0008 (13)	−0.0042 (14)
C21	0.0471 (16)	0.0456 (15)	0.0408 (16)	0.0078 (14)	0.0020 (13)	−0.0045 (14)
C22	0.0557 (18)	0.0656 (19)	0.0532 (17)	−0.0046 (17)	0.0131 (16)	−0.0008 (17)
O4A	0.132 (9)	0.072 (5)	0.075 (5)	−0.014 (5)	0.053 (6)	−0.031 (4)
O5A	0.085 (3)	0.096 (6)	0.117 (7)	−0.003 (3)	−0.020 (3)	−0.061 (5)
O4B	0.073 (5)	0.095 (10)	0.125 (13)	0.021 (6)	0.005 (8)	−0.052 (9)
O5B	0.194 (12)	0.035 (4)	0.112 (9)	−0.022 (5)	0.071 (9)	−0.015 (4)

O1—N1	1.230 (5)	C8—H8	0.9300
O2—N1	1.230 (4)	C9—C10	1.428 (5)
O3—C6	1.378 (4)	C10—H10	0.9300
O3—C11	1.436 (5)	C11—H11A	0.9600
O6—C20	1.386 (4)	C11—H11B	0.9600
O6—C22	1.447 (4)	C11—H11C	0.9600
N1—C1	1.483 (5)	C12—C21	1.387 (5)
N2—O4A	1.193 (12)	C12—C13	1.440 (5)
N2—O4B	1.206 (17)	C13—C14	1.436 (5)
N2—O5A	1.250 (5)	C13—C18	1.449 (5)
N2—O5B	1.292 (7)	C14—C15	1.383 (5)
N2—C12	1.494 (4)	C14—H14	0.9300
C1—C10	1.357 (5)	C15—C16	1.412 (5)
C1—C2	1.424 (5)	C15—H15	0.9300
C2—C3	1.376 (5)	C16—C17	1.381 (5)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.428 (5)	C17—C18	1.448 (5)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.437 (5)	C18—C19	1.442 (4)
C4—C9	1.447 (5)	C19—C20	1.408 (4)
C5—C6	1.398 (5)	C20—C21	1.416 (4)
C5—C19	1.510 (5)	C21—H21	0.9300
C6—C7	1.433 (5)	C22—H22A	0.9600
C7—C8	1.371 (5)	C22—H22B	0.9600
C7—H7	0.9300	C22—H22C	0.9600
C8—C9	1.419 (5)
C6—O3—C11	118.9 (2)	C9—C10—H10	120.2
C20—O6—C22	118.7 (2)	O3—C11—H11A	109.5
O1—N1—O2	122.6 (3)	O3—C11—H11B	109.5
O1—N1—C1	118.0 (3)	H11A—C11—H11B	109.5
O2—N1—C1	119.4 (3)	O3—C11—H11C	109.5
O4A—N2—O4B	34.8 (7)	H11A—C11—H11C	109.5
O4A—N2—O5A	106.8 (8)	H11B—C11—H11C	109.5
O4B—N2—O5A	123.8 (9)	C21—C12—C13	123.8 (3)
O4A—N2—O5B	118.1 (8)	C21—C12—N2	115.0 (3)
O4B—N2—O5B	98.9 (13)	C13—C12—N2	121.3 (3)
O5A—N2—O5B	58.9 (5)	C14—C13—C12	126.2 (3)
O4A—N2—C12	121.1 (6)	C14—C13—C18	118.7 (3)
O4B—N2—C12	117.6 (8)	C12—C13—C18	115.1 (2)
O5A—N2—C12	118.5 (4)	C15—C14—C13	121.3 (3)
O5B—N2—C12	116.9 (4)	C15—C14—H14	119.4
C10—C1—C2	122.4 (3)	C13—C14—H14	119.4
C10—C1—N1	119.6 (3)	C14—C15—C16	120.6 (3)
C2—C1—N1	118.0 (3)	C14—C15—H15	119.7
C3—C2—C1	119.0 (3)	C16—C15—H15	119.7
C3—C2—H2	120.5	C17—C16—C15	120.0 (3)
C1—C2—H2	120.5	C17—C16—H16	120.0
C2—C3—C4	121.6 (3)	C15—C16—H16	120.0
C2—C3—H3	119.2	C16—C17—C18	121.9 (3)
C4—C3—H3	119.2	C16—C17—H17	119.0
C3—C4—C5	122.1 (2)	C18—C17—H17	119.0
C3—C4—C9	117.7 (3)	C19—C18—C17	121.2 (3)
C5—C4—C9	120.2 (3)	C19—C18—C13	121.4 (3)
C6—C5—C4	118.8 (2)	C17—C18—C13	117.4 (2)
C6—C5—C19	120.0 (2)	C20—C19—C18	119.7 (3)
C4—C5—C19	121.2 (3)	C20—C19—C5	119.5 (2)
O3—C6—C5	116.0 (2)	C18—C19—C5	120.7 (2)
O3—C6—C7	123.1 (3)	O6—C20—C19	117.1 (2)
C5—C6—C7	120.9 (3)	O6—C20—C21	122.9 (3)
C8—C7—C6	120.3 (3)	C19—C20—C21	120.0 (2)
C8—C7—H7	119.8	C12—C21—C20	120.0 (3)
C6—C7—H7	119.8	C12—C21—H21	120.0
C7—C8—C9	121.5 (2)	C20—C21—H21	120.0
C7—C8—H8	119.2	O6—C22—H22A	109.5
C9—C8—H8	119.2	O6—C22—H22B	109.5
C8—C9—C10	122.1 (2)	H22A—C22—H22B	109.5
C8—C9—C4	118.3 (3)	O6—C22—H22C	109.5
C10—C9—C4	119.6 (3)	H22A—C22—H22C	109.5
C1—C10—C9	119.6 (3)	H22B—C22—H22C	109.5
C1—C10—H10	120.2
O1—N1—C1—C10	−168.7 (3)	O4B—N2—C12—C13	−148.8 (11)
O2—N1—C1—C10	8.6 (5)	O5A—N2—C12—C13	36.0 (7)
O1—N1—C1—C2	10.1 (5)	O5B—N2—C12—C13	−31.5 (11)
O2—N1—C1—C2	−172.6 (3)	C21—C12—C13—C14	−179.3 (3)
C10—C1—C2—C3	−3.1 (4)	N2—C12—C13—C14	0.5 (4)
N1—C1—C2—C3	178.2 (3)	C21—C12—C13—C18	0.0 (4)
C1—C2—C3—C4	−0.2 (4)	N2—C12—C13—C18	179.7 (2)
C2—C3—C4—C5	−177.3 (3)	C12—C13—C14—C15	178.6 (3)
C2—C3—C4—C9	3.5 (4)	C18—C13—C14—C15	−0.6 (4)
C3—C4—C5—C6	−178.3 (3)	C13—C14—C15—C16	1.7 (4)
C9—C4—C5—C6	0.9 (4)	C14—C15—C16—C17	−1.4 (5)
C3—C4—C5—C19	2.3 (4)	C15—C16—C17—C18	−0.1 (4)
C9—C4—C5—C19	−178.4 (2)	C16—C17—C18—C19	−178.5 (3)
C11—O3—C6—C5	−172.4 (3)	C16—C17—C18—C13	1.2 (4)
C11—O3—C6—C7	8.0 (4)	C14—C13—C18—C19	178.8 (2)
C4—C5—C6—O3	−178.0 (2)	C12—C13—C18—C19	−0.5 (3)
C19—C5—C6—O3	1.4 (4)	C14—C13—C18—C17	−0.9 (3)
C4—C5—C6—C7	1.6 (4)	C12—C13—C18—C17	179.8 (2)
C19—C5—C6—C7	−179.1 (2)	C17—C18—C19—C20	−179.4 (2)
O3—C6—C7—C8	177.5 (3)	C13—C18—C19—C20	0.9 (4)
C5—C6—C7—C8	−2.1 (4)	C17—C18—C19—C5	−1.8 (4)
C6—C7—C8—C9	0.0 (5)	C13—C18—C19—C5	178.6 (2)
C7—C8—C9—C10	−177.4 (3)	C6—C5—C19—C20	−114.4 (3)
C7—C8—C9—C4	2.5 (4)	C4—C5—C19—C20	64.9 (3)
C3—C4—C9—C8	176.4 (2)	C6—C5—C19—C18	68.0 (3)
C5—C4—C9—C8	−2.9 (4)	C4—C5—C19—C18	−112.7 (3)
C3—C4—C9—C10	−3.8 (4)	C22—O6—C20—C19	−166.9 (2)
C5—C4—C9—C10	176.9 (3)	C22—O6—C20—C21	15.2 (4)
C2—C1—C10—C9	2.7 (5)	C18—C19—C20—O6	−178.8 (2)
N1—C1—C10—C9	−178.5 (2)	C5—C19—C20—O6	3.5 (3)
C8—C9—C10—C1	−179.3 (3)	C18—C19—C20—C21	−0.8 (4)
C4—C9—C10—C1	0.8 (4)	C5—C19—C20—C21	−178.5 (2)
O4A—N2—C12—C21	−9.0 (9)	C13—C12—C21—C20	0.1 (4)
O4B—N2—C12—C21	30.9 (12)	N2—C12—C21—C20	−179.6 (2)
O5A—N2—C12—C21	−144.3 (7)	O6—C20—C21—C12	178.2 (2)
O5B—N2—C12—C21	148.3 (10)	C19—C20—C21—C12	0.3 (4)
O4A—N2—C12—C13	171.3 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2i	0.93	2.59	3.361 (10)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O2i	0.93	2.59	3.361 (10)	140

Symmetry code: (i) .