9,9′-Biacridine N,N′-dioxide: a novel potential bridging ligand bearing the bulky acridine N-oxide skeleton

The title compound, C₂₆H₁₆N₂O₂, is a potential linear bridging O-donor ligand comprising bulky acridine N-oxide ring systems. Weak inter­molecular C—H...O hydrogen-bonding inter­actions link adjacent mol­ecules to form extended chains. The structure also contains inter­molecular C—H...π inter­actions.

S1. Comment

In recent years, 4,4'-bipyridine, (A), and its analogues containing two 4-pyridyl donor units have been used extensively as bridging ligands in coordination and metallosupramolecular chemistry (Kitagawa et al., 2004; Steel, 2005), and this has resulted in a large number of extended assemblies including helical networks and diamondoid, honeycomb, square-grid, ribbon, grid, T-shaped, ladder, brick wall and octahedral frameworks (Withersby et al., 1999; Yaghi et al., 1998). In comparison with other N-containing heterocyclic ligands, acridine-based ligands have some primary structural characteristics: (a) the acridine ring has a larger conjugated π system and therefore π–π stacking interactions may play important roles in the formation of their metal complexes and (b) the larger conjugated π systems and the steric hindrance between H atoms of adjacent benzene rings may affect the coordination abilities of the acridine N donor atom (Bu et al., 2004; Liu et al., 2006). To explore the influence of the bulky acridine-based ligand with a large conjugated π system on the structures and properties of its complexes, we synthesized a 4,4'-bipyridyl-like linear diamine bridging ligand, 9,9'-biacridine, (B), and reported its crystal structure (Liu, 2007). Unfortunately, unlike 4,4'-bipyridine, when we sequentially reacted 9,9'-biacridine with various metal salts in order to construct related metal-organic complexes, no complexes suitable for a crystal structure determination could be obtained; this may be due to the steric hindrance between the H atoms of the adjacent benzene rings.

Recently, we also noticed that Long et al. (2001) have demonstrated the use of 4,4'-bipyridine N,N'-dioxide, (C), in the construction of lanthanide coordination polymers with unusual two- or three-dimensional networks. Considering all of the aspects stated above, we sequentially synthesized a novel linear bridging ligand with a bulky aromatic skeleton, viz. 9,9'-biacridine N,N'-dioxide, (I), whose coordination sites could potentially mimic those of 4,4'-bipyridyl N,N'-dioxide in supramolecular chemistry, except for the bulky aromatic skeleton. In comparision with 9,9'-biacridine, the N—O bonds of (I) may reduce the steric hindrance of the H atoms of the adjacent benzene rings so as to facilitate the formation of coordination bonds between metal ions and the O donors of the acridine N-oxide rings in the construction of unique supramolecular architetures with potential uses as functional materials. We report here the crystal structure of (I) and compare it with a structurally related compound, 10,10'-biacridinyl-9,9'-dione (Scheme 2) whose crystal structure has been reported by Boyer et al. (1993).

The bond distances and angles in (I) (Fig. 1) have normal values, and are comparable to those observed for similar acridine-based molecules (Boyer et al., 1999; Liu et al., 2006). Each of the acridine N-oxide ring systems in the molecule is essentially planar, but the planes are twisted away from one another by an angle of 76.24 (9)°. In comparison with (I), the dihedral angles between the planes of the acridine rings in (B) and 10,10'-biacridinyl-9,9'-dione (Scheme 2) show an even greater degree of perpendicularity, at 84.67 (7) and 85.3 (3)°, respectively (Liu, 2007; Boyer et al., 1993).

In the crystal structure of (I), adjacent molecules are linked into an extended chain along the [201] direction by two distinct intermolecular C—H···O hydrogen-bonding interactions (Fig. 2 and Table 1) (Desiraju & Steiner, 1999). The interaction involving the C8/H8 group as a donor links pairs of molecules into centrosymmetric dimers, and this hydrogen-bond pattern can be described by a graph-set motif of R²₂(18) (Bernstein et al., 1995). The interaction involving the C16/H16 group also links pairs of molecules via another R²₂(18) motif into dimers with C₂ symmetry, but the acceptor molecule for the C16/H16 interaction is not the same as that for the C8/H8 interaction. The combination of both types of C—H···O interactions links these dimers continuously into an extended chain structure. Adjacent chains are cross-linked via intermolecular C—H···π interactions (Table 1) involving the C1/C6/C7/C12/C13/N2 pyridine ring (centroid Cg1). The net result is a two-dimensional network running parallel to the (010) plane (Fig. 2). In the adjacent chains, the acridine ring systems are arranged in an edge-to-face orientation (Sony & Ponnuswamy, 2006).

Related literature

For related literature, see: Boyer et al. (1993, 1999); Desiraju & Steiner (1999); Kitagawa et al. (2004); Liu (2007); Liu et al. (2006); Long et al. (2001); Simpson et al. (1963); Sony & Ponnuswamy (2006); Steel (2005); Withersby et al. (1999); Yaghi et al. (1998).

S2. Experimental

Compound (I) was synthesized according to a method reported in the literature (Boyer et al., 1999; Simpson et al., 1963). A mixed solution of (I) (0.1 mmol) in methanol and CH₂Cl₂ (10 ml, v/v 1:1) was filtered and the resulting solution was kept at room temperature. Yellow single crystals suitable for X-ray analysis were obtained by slow evaporation of the solvent after several days (yield 30%, m.p. > 573 K). Analysis calculated for C₂₆H₁₆N₂O₂: C 80.40, H 4.15, N 7.21%; found: C 80.55, H 4.09, N 7.07%.

S3. Refinement

H atoms were included in calculated positions and treated in the subsequent refinement as riding atoms [C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C)].

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL (Bruker, 1998) and PLATON (Spek, 2003).

Figures

	Fig. 1. The asymmetric unit of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal packing, showing the two-dimensional network in the title compound formed by the co-effects of intermolecular C—H···O hydrogen bonds (thin dashed lines) and C—H···π interactions (thick dashed lines). For clarity, only H atoms involved in the interactions are shown.

9,9'-Biacridine N,N'-dioxide

Crystal data

C26H16N2O2	F(000) = 1616
Mr = 388.41	Dx = 1.378 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 553 reflections
a = 9.251 (3) Å	θ = 2.6–20.1°
b = 14.972 (5) Å	µ = 0.09 mm^−1
c = 27.35 (1) Å	T = 293 K
β = 98.791 (6)°	Prism, yellow
V = 3744 (2) Å^3	0.30 × 0.25 × 0.18 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer	1532 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.087
Graphite monochromator	θmax = 25.0°, θmin = 1.5°
ϕ and ω scans	h = −10→9
9593 measured reflections	k = −14→17
3304 independent reflections	l = −31→32

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.183	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0825P)^2] where P = (Fo^2 + 2Fc^2)/3
3304 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4259 (4)	0.5903 (4)	0.30375 (13)	0.0583 (12)
C2	0.3417 (5)	0.6578 (5)	0.27816 (16)	0.0855 (17)
H2	0.2649	0.6430	0.2534	0.103*
C3	0.3714 (6)	0.7442 (5)	0.28919 (19)	0.102 (2)
H3	0.3123	0.7884	0.2727	0.122*
C4	0.4903 (6)	0.7688 (4)	0.32515 (17)	0.0907 (16)
H4	0.5118	0.8287	0.3317	0.109*
C5	0.5728 (4)	0.7038 (3)	0.35004 (14)	0.0647 (13)
H5	0.6510	0.7201	0.3739	0.078*
C6	0.5443 (4)	0.6114 (3)	0.34108 (12)	0.0491 (10)
C7	0.5874 (4)	0.4556 (3)	0.35737 (12)	0.0450 (10)
C8	0.6614 (4)	0.3833 (3)	0.38325 (14)	0.0561 (11)
H8	0.7380	0.3947	0.4087	0.067*
C9	0.6233 (5)	0.2975 (3)	0.37177 (17)	0.0771 (14)
H9	0.6731	0.2506	0.3892	0.092*
C10	0.5084 (6)	0.2800 (4)	0.3335 (2)	0.0953 (18)
H10	0.4834	0.2210	0.3255	0.114*
C11	0.4333 (5)	0.3459 (4)	0.30779 (18)	0.0861 (17)
H11	0.3566	0.3326	0.2827	0.103*
C12	0.4716 (4)	0.4352 (3)	0.31908 (14)	0.0566 (12)
C13	0.6242 (3)	0.5452 (3)	0.36816 (11)	0.0379 (9)
C14	0.7468 (4)	0.5678 (2)	0.40817 (12)	0.0366 (9)
C15	0.8922 (4)	0.5595 (2)	0.39983 (12)	0.0397 (9)
C16	0.9306 (4)	0.5316 (2)	0.35341 (13)	0.0481 (10)
H16	0.8572	0.5189	0.3271	0.058*
C17	1.0728 (4)	0.5237 (3)	0.34734 (15)	0.0601 (12)
H17	1.0962	0.5056	0.3170	0.072*
C18	1.1846 (4)	0.5425 (3)	0.38668 (16)	0.0674 (13)
H18	1.2816	0.5357	0.3821	0.081*
C19	1.1546 (4)	0.5704 (3)	0.43116 (15)	0.0578 (11)
H19	1.2303	0.5835	0.4566	0.069*
C20	1.0081 (4)	0.5795 (2)	0.43852 (13)	0.0427 (9)
C21	0.8372 (4)	0.6182 (2)	0.49243 (12)	0.0407 (9)
C22	0.8115 (5)	0.6490 (2)	0.53895 (13)	0.0564 (11)
H22	0.8896	0.6626	0.5635	0.068*
C23	0.6726 (5)	0.6588 (3)	0.54779 (14)	0.0644 (12)
H23	0.6561	0.6794	0.5785	0.077*
C24	0.5530 (4)	0.6386 (3)	0.51159 (14)	0.0648 (12)
H24	0.4581	0.6460	0.5182	0.078*
C25	0.5767 (4)	0.6079 (3)	0.46647 (13)	0.0563 (11)
H25	0.4968	0.5936	0.4428	0.068*
C26	0.7196 (4)	0.5972 (2)	0.45475 (12)	0.0394 (9)
N1	0.9788 (3)	0.6082 (2)	0.48401 (10)	0.0474 (8)
N2	0.3938 (3)	0.5018 (3)	0.29254 (11)	0.0646 (11)
O1	1.0863 (3)	0.6257 (2)	0.51898 (9)	0.0725 (9)
O2	0.2880 (3)	0.4824 (2)	0.25739 (10)	0.0980 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.038 (2)	0.106 (4)	0.029 (2)	0.013 (3)	−0.0005 (18)	−0.001 (3)
C2	0.056 (3)	0.155 (6)	0.042 (3)	0.024 (4)	−0.005 (2)	0.004 (3)
C3	0.095 (4)	0.140 (6)	0.065 (4)	0.059 (4)	−0.004 (3)	0.023 (4)
C4	0.112 (4)	0.088 (4)	0.070 (3)	0.045 (3)	0.007 (3)	0.014 (3)
C5	0.071 (3)	0.080 (4)	0.041 (2)	0.024 (3)	0.000 (2)	0.000 (2)
C6	0.040 (2)	0.073 (3)	0.035 (2)	0.011 (2)	0.0065 (17)	0.001 (2)
C7	0.036 (2)	0.067 (3)	0.033 (2)	−0.006 (2)	0.0097 (17)	−0.011 (2)
C8	0.053 (3)	0.064 (3)	0.053 (3)	−0.010 (2)	0.012 (2)	−0.005 (2)
C9	0.092 (4)	0.063 (4)	0.079 (3)	−0.017 (3)	0.024 (3)	−0.007 (3)
C10	0.111 (5)	0.088 (5)	0.093 (4)	−0.048 (4)	0.037 (4)	−0.039 (4)
C11	0.077 (4)	0.114 (5)	0.068 (3)	−0.041 (4)	0.011 (3)	−0.042 (3)
C12	0.043 (2)	0.090 (4)	0.037 (2)	−0.016 (3)	0.008 (2)	−0.018 (2)
C13	0.030 (2)	0.056 (3)	0.0283 (19)	−0.0017 (19)	0.0046 (16)	−0.0059 (18)
C14	0.037 (2)	0.040 (2)	0.031 (2)	−0.0025 (17)	0.0010 (16)	−0.0009 (16)
C15	0.036 (2)	0.046 (3)	0.036 (2)	−0.0036 (17)	0.0018 (17)	0.0032 (17)
C16	0.045 (2)	0.058 (3)	0.042 (2)	−0.001 (2)	0.0092 (18)	0.0015 (19)
C17	0.050 (3)	0.072 (3)	0.060 (3)	−0.001 (2)	0.016 (2)	−0.006 (2)
C18	0.042 (3)	0.092 (4)	0.072 (3)	−0.003 (2)	0.020 (2)	0.006 (3)
C19	0.035 (2)	0.076 (3)	0.060 (3)	−0.006 (2)	0.000 (2)	0.003 (2)
C20	0.039 (2)	0.049 (3)	0.039 (2)	−0.0014 (18)	0.0022 (18)	0.0040 (19)
C21	0.045 (2)	0.047 (3)	0.029 (2)	−0.0016 (19)	0.0025 (17)	0.0019 (17)
C22	0.062 (3)	0.067 (3)	0.038 (2)	−0.005 (2)	0.001 (2)	−0.005 (2)
C23	0.078 (3)	0.079 (4)	0.037 (2)	−0.007 (3)	0.014 (2)	−0.015 (2)
C24	0.057 (3)	0.087 (4)	0.052 (3)	−0.003 (2)	0.017 (2)	−0.013 (2)
C25	0.044 (2)	0.082 (3)	0.042 (2)	−0.008 (2)	0.0061 (18)	−0.011 (2)
C26	0.038 (2)	0.046 (3)	0.033 (2)	−0.0048 (18)	0.0005 (17)	−0.0001 (17)
N1	0.042 (2)	0.061 (2)	0.0348 (18)	−0.0063 (16)	−0.0065 (15)	−0.0006 (16)
N2	0.034 (2)	0.126 (4)	0.0328 (19)	−0.008 (2)	0.0016 (16)	−0.018 (2)
O1	0.0514 (17)	0.104 (3)	0.0527 (17)	−0.0102 (16)	−0.0213 (14)	−0.0100 (16)
O2	0.0505 (19)	0.189 (4)	0.0477 (17)	−0.021 (2)	−0.0128 (15)	−0.029 (2)

Geometric parameters (Å, º)

C1—N2	1.381 (5)	C14—C26	1.406 (4)
C1—C2	1.397 (6)	C15—C20	1.419 (4)
C1—C6	1.415 (5)	C15—C16	1.432 (5)
C2—C3	1.348 (7)	C16—C17	1.356 (5)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.408 (7)	C17—C18	1.403 (5)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.355 (5)	C18—C19	1.355 (5)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.421 (5)	C19—C20	1.407 (5)
C5—H5	0.9300	C19—H19	0.9300
C6—C13	1.383 (5)	C20—N1	1.382 (4)
C7—C13	1.404 (5)	C21—N1	1.372 (4)
C7—C12	1.412 (5)	C21—C22	1.407 (5)
C7—C8	1.413 (5)	C21—C26	1.415 (4)
C8—C9	1.356 (5)	C22—C23	1.351 (5)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.398 (6)	C23—C24	1.401 (5)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.342 (6)	C24—C25	1.365 (5)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.406 (6)	C25—C26	1.416 (5)
C11—H11	0.9300	C25—H25	0.9300
C12—N2	1.371 (5)	N1—O1	1.297 (3)
C13—C14	1.490 (4)	N2—O2	1.296 (4)
C14—C15	1.404 (4)
N2—C1—C2	119.8 (4)	C14—C15—C20	119.6 (3)
N2—C1—C6	119.4 (4)	C14—C15—C16	122.9 (3)
C2—C1—C6	120.7 (5)	C20—C15—C16	117.5 (3)
C3—C2—C1	120.2 (5)	C17—C16—C15	120.7 (3)
C3—C2—H2	119.9	C17—C16—H16	119.6
C1—C2—H2	119.9	C15—C16—H16	119.6
C2—C3—C4	121.2 (5)	C16—C17—C18	120.3 (4)
C2—C3—H3	119.4	C16—C17—H17	119.9
C4—C3—H3	119.4	C18—C17—H17	119.9
C5—C4—C3	118.9 (5)	C19—C18—C17	121.5 (4)
C5—C4—H4	120.6	C19—C18—H18	119.3
C3—C4—H4	120.6	C17—C18—H18	119.3
C4—C5—C6	122.5 (4)	C18—C19—C20	119.5 (4)
C4—C5—H5	118.8	C18—C19—H19	120.2
C6—C5—H5	118.8	C20—C19—H19	120.2
C13—C6—C1	121.2 (4)	N1—C20—C19	119.0 (3)
C13—C6—C5	122.4 (3)	N1—C20—C15	120.5 (3)
C1—C6—C5	116.4 (4)	C19—C20—C15	120.5 (3)
C13—C7—C12	119.6 (4)	N1—C21—C22	119.0 (3)
C13—C7—C8	123.0 (3)	N1—C21—C26	120.1 (3)
C12—C7—C8	117.4 (4)	C22—C21—C26	120.9 (4)
C9—C8—C7	121.4 (4)	C23—C22—C21	119.6 (4)
C9—C8—H8	119.3	C23—C22—H22	120.2
C7—C8—H8	119.3	C21—C22—H22	120.2
C8—C9—C10	119.5 (5)	C22—C23—C24	121.3 (4)
C8—C9—H9	120.3	C22—C23—H23	119.3
C10—C9—H9	120.3	C24—C23—H23	119.3
C11—C10—C9	121.8 (5)	C25—C24—C23	119.5 (4)
C11—C10—H10	119.1	C25—C24—H24	120.2
C9—C10—H10	119.1	C23—C24—H24	120.2
C10—C11—C12	119.5 (5)	C24—C25—C26	121.8 (3)
C10—C11—H11	120.3	C24—C25—H25	119.1
C12—C11—H11	120.3	C26—C25—H25	119.1
N2—C12—C11	118.8 (4)	C14—C26—C21	120.4 (3)
N2—C12—C7	120.9 (4)	C14—C26—C25	122.9 (3)
C11—C12—C7	120.4 (5)	C21—C26—C25	116.8 (3)
C6—C13—C7	118.7 (3)	O1—N1—C21	119.9 (3)
C6—C13—C14	121.0 (3)	O1—N1—C20	119.5 (3)
C7—C13—C14	120.3 (3)	C21—N1—C20	120.6 (3)
C15—C14—C26	118.9 (3)	O2—N2—C12	120.4 (4)
C15—C14—C13	120.1 (3)	O2—N2—C1	119.5 (4)
C26—C14—C13	121.0 (3)	C12—N2—C1	120.1 (3)
N2—C1—C2—C3	179.4 (4)	C15—C16—C17—C18	0.1 (6)
C6—C1—C2—C3	−0.8 (7)	C16—C17—C18—C19	−1.1 (6)
C1—C2—C3—C4	2.4 (8)	C17—C18—C19—C20	1.0 (6)
C2—C3—C4—C5	−2.1 (8)	C18—C19—C20—N1	−179.8 (4)
C3—C4—C5—C6	0.3 (7)	C18—C19—C20—C15	0.2 (6)
N2—C1—C6—C13	−3.1 (5)	C14—C15—C20—N1	−0.9 (5)
C2—C1—C6—C13	177.1 (4)	C16—C15—C20—N1	178.9 (3)
N2—C1—C6—C5	178.8 (3)	C14—C15—C20—C19	179.1 (3)
C2—C1—C6—C5	−1.0 (5)	C16—C15—C20—C19	−1.1 (5)
C4—C5—C6—C13	−176.8 (4)	N1—C21—C22—C23	−179.7 (4)
C4—C5—C6—C1	1.2 (6)	C26—C21—C22—C23	−0.1 (5)
C13—C7—C8—C9	−179.8 (3)	C21—C22—C23—C24	0.2 (6)
C12—C7—C8—C9	0.1 (5)	C22—C23—C24—C25	0.4 (6)
C7—C8—C9—C10	0.1 (6)	C23—C24—C25—C26	−1.1 (6)
C8—C9—C10—C11	−0.6 (8)	C15—C14—C26—C21	0.2 (5)
C9—C10—C11—C12	0.8 (8)	C13—C14—C26—C21	179.8 (3)
C10—C11—C12—N2	−180.0 (4)	C15—C14—C26—C25	179.8 (3)
C10—C11—C12—C7	−0.5 (7)	C13—C14—C26—C25	−0.6 (5)
C13—C7—C12—N2	−0.5 (5)	N1—C21—C26—C14	−1.4 (5)
C8—C7—C12—N2	179.5 (3)	C22—C21—C26—C14	179.0 (3)
C13—C7—C12—C11	−180.0 (3)	N1—C21—C26—C25	179.0 (3)
C8—C7—C12—C11	0.0 (5)	C22—C21—C26—C25	−0.6 (5)
C1—C6—C13—C7	1.1 (5)	C24—C25—C26—C14	−178.4 (4)
C5—C6—C13—C7	179.1 (3)	C24—C25—C26—C21	1.2 (5)
C1—C6—C13—C14	−178.7 (3)	C22—C21—N1—O1	1.2 (5)
C5—C6—C13—C14	−0.8 (5)	C26—C21—N1—O1	−178.5 (3)
C12—C7—C13—C6	0.7 (5)	C22—C21—N1—C20	−179.0 (3)
C8—C7—C13—C6	−179.4 (3)	C26—C21—N1—C20	1.4 (5)
C12—C7—C13—C14	−179.5 (3)	C19—C20—N1—O1	−0.4 (5)
C8—C7—C13—C14	0.5 (5)	C15—C20—N1—O1	179.6 (3)
C6—C13—C14—C15	−102.9 (4)	C19—C20—N1—C21	179.7 (3)
C7—C13—C14—C15	77.3 (4)	C15—C20—N1—C21	−0.3 (5)
C6—C13—C14—C26	77.5 (4)	C11—C12—N2—O2	−0.7 (5)
C7—C13—C14—C26	−102.3 (4)	C7—C12—N2—O2	179.8 (3)
C26—C14—C15—C20	0.9 (5)	C11—C12—N2—C1	178.0 (4)
C13—C14—C15—C20	−178.7 (3)	C7—C12—N2—C1	−1.4 (5)
C26—C14—C15—C16	−178.9 (3)	C2—C1—N2—O2	1.8 (5)
C13—C14—C15—C16	1.5 (5)	C6—C1—N2—O2	−178.0 (3)
C14—C15—C16—C17	−179.3 (4)	C2—C1—N2—C12	−177.0 (4)
C20—C15—C16—C17	1.0 (5)	C6—C1—N2—C12	3.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1^i	0.93	2.38	3.272 (5)	161
C16—H16···O2^ii	0.93	2.55	3.456 (5)	165
C18—H18···Cg1^iii	0.93	2.71	3.579 (5)	156

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, y, −z+1/2; (iii) x+1, y, z.