1-(Prop-2-en-1-yl)-3-{[3-(pyridin-4-yl)-4,5-di-hydro-isoxazol-5-yl]meth-yl}-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione.

The fused five- and three six-membered rings of the anthra[1,2-d]imidazole-trione part of the title compound, C27H20N4O4, show two different substituents at the imidazole N atoms, viz. an allyl group and a [3-(pyridin-4-yl)-4,5-di-hydro-isoxazol-5-yl]methyl group. The fused-ring system is approximately planar [r.m.s. deviation = 0.232 (2) Å], but is slightly buckled along the common edge of the two pairs of adjacent rings, with a dihedral angle between them of 11.17 (6)°. The isoxazole ring makes dihedral angles of 27.2 (2) and 12.7 (2)° with the imidazole and pyridine rings, respectively. Weak C-H⋯O and C-H⋯N hydrogen bonds ensure the cohesion of the crystal structure, forming a three-dimensional network.

Related literature

For the use of anthra­quinone as an organic redox mediator, see: Campos-Martin et al. (2006 ▶); Harish et al. (2009 ▶); Jürmann et al. (2007 ▶); Manisankar & Gomathi (2005 ▶). For the biological activity of anthra­quinone derivatives, see: Henderson et al. (1998 ▶); Barasch et al. (1999 ▶); Dou et al. (2009 ▶). For background to pH sensor applications, see: Wong et al. (2004 ▶); Lafitte et al. (2008 ▶); Wildgoose et al. (2003 ▶). For similar compounds, see: Afrakssou et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C27H20N4O4

M = 464.47

Triclinic,

a = 8.0930 (2) Å

b = 12.1191 (3) Å

c = 12.2743 (2) Å

α = 87.109 (1)°

β = 73.612 (1)°

γ = 72.283 (1)°

V = 1099.35 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.14 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

36799 measured reflections

5659 independent reflections

3900 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.148

S = 1.02

5659 reflections

316 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus; 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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681301369X/im2433sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301369X/im2433Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301369X/im2433Isup3.cml

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

C27H20N4O4	Z = 2
Mr = 464.47	F(000) = 484
Triclinic, P1	Dx = 1.403 Mg m−3
Hall symbol: -P 1	Melting point: 443 K
a = 8.0930 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.1191 (3) Å	Cell parameters from 8485 reflections
c = 12.2743 (2) Å	θ = 2.8–26.0°
α = 87.109 (1)°	µ = 0.10 mm−1
β = 73.612 (1)°	T = 296 K
γ = 72.283 (1)°	Block, orange
V = 1099.35 (4) Å3	0.14 × 0.10 × 0.08 mm

Bruker APEXII CCD diffractometer	3900 reflections with I > 2σ(I)
Radiation source: microfocus source	Rint = 0.031
Graphite monochromator	θmax = 28.7°, θmin = 1.7°
φ and ω scans	h = −10→10
36799 measured reflections	k = −16→16
5659 independent reflections	l = −16→16

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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F2) = 0.148	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0711P)2 + 0.2464P] where P = (Fo2 + 2Fc2)/3
5659 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.5114 (2)	0.62606 (14)	1.11854 (16)	0.0495 (4)
C2	0.3824 (3)	0.73461 (16)	1.1261 (2)	0.0637 (5)
H2	0.3864	0.7808	1.0631	0.076*
C3	0.2504 (3)	0.77342 (18)	1.2256 (2)	0.0742 (7)
H3	0.1658	0.8462	1.2302	0.089*
C4	0.2421 (3)	0.70528 (19)	1.3189 (2)	0.0739 (6)
H4	0.1509	0.7316	1.3860	0.089*
C5	0.3689 (3)	0.59784 (17)	1.31336 (19)	0.0637 (5)
H5	0.3630	0.5521	1.3766	0.076*
C6	0.5051 (2)	0.55819 (14)	1.21343 (15)	0.0488 (4)
C7	0.6385 (2)	0.44158 (14)	1.20925 (14)	0.0463 (4)
C8	0.7922 (2)	0.40617 (13)	1.10555 (13)	0.0383 (3)
C9	0.7841 (2)	0.46768 (13)	1.00512 (13)	0.0417 (3)
C10	0.6459 (2)	0.58148 (15)	1.00850 (16)	0.0498 (4)
C11	0.93761 (19)	0.30551 (12)	1.09642 (12)	0.0362 (3)
C12	1.0529 (2)	0.26122 (13)	0.98806 (12)	0.0376 (3)
C13	1.0379 (2)	0.31860 (15)	0.89005 (13)	0.0464 (4)
H13	1.1144	0.2877	0.8194	0.056*
C14	0.9049 (2)	0.42393 (15)	0.90068 (14)	0.0478 (4)
H14	0.8960	0.4666	0.8363	0.057*
C15	1.1529 (2)	0.14078 (13)	1.11712 (13)	0.0382 (3)
C16	0.9718 (2)	0.24952 (15)	1.29631 (13)	0.0481 (4)
H16A	1.0353	0.1796	1.3274	0.058*
H16B	0.8438	0.2670	1.3348	0.058*
C17	1.0362 (3)	0.34735 (19)	1.31752 (16)	0.0659 (5)
H17	1.1552	0.3440	1.2807	0.079*
C18	0.9359 (5)	0.4370 (2)	1.3844 (2)	0.1064 (10)
H18A	0.8164	0.4428	1.4223	0.128*
H18B	0.9836	0.4953	1.3942	0.128*
C19	1.3115 (2)	0.07767 (14)	0.91585 (13)	0.0418 (4)
H19A	1.4231	0.0492	0.9374	0.050*
H19B	1.3360	0.1169	0.8450	0.050*
C20	1.2483 (2)	−0.02358 (14)	0.89840 (13)	0.0426 (4)
H20	1.2199	−0.0630	0.9698	0.051*
C21	1.3846 (2)	−0.10974 (14)	0.80505 (14)	0.0473 (4)
H21A	1.5044	−0.1010	0.7885	0.057*
H21B	1.3904	−0.1891	0.8245	0.057*
C22	1.3037 (2)	−0.07338 (14)	0.70869 (13)	0.0433 (4)
C23	1.3916 (2)	−0.11054 (15)	0.58912 (14)	0.0464 (4)
C24	1.5579 (3)	−0.19406 (17)	0.55610 (16)	0.0622 (5)
H24	1.6145	−0.2309	0.6101	0.075*
C25	1.6397 (3)	−0.2224 (2)	0.44121 (19)	0.0754 (6)
H25	1.7517	−0.2789	0.4207	0.090*
C26	1.4083 (4)	−0.0959 (2)	0.39166 (17)	0.0716 (6)
H26	1.3550	−0.0618	0.3354	0.086*
C27	1.3145 (3)	−0.06123 (18)	0.50314 (15)	0.0581 (5)
H27	1.2015	−0.0057	0.5206	0.070*
N1	1.00212 (17)	0.22965 (11)	1.17475 (10)	0.0385 (3)
N2	1.17735 (17)	0.15961 (11)	1.00326 (10)	0.0391 (3)
N3	1.14308 (19)	−0.00366 (13)	0.73868 (12)	0.0502 (4)
N4	1.5695 (3)	−0.17468 (18)	0.35938 (15)	0.0773 (6)
O1	0.61239 (19)	0.37492 (12)	1.28523 (12)	0.0702 (4)
O2	0.6424 (2)	0.63732 (13)	0.92318 (13)	0.0750 (4)
O3	1.24659 (15)	0.06244 (10)	1.15952 (9)	0.0478 (3)
O4	1.08962 (15)	0.01876 (11)	0.85700 (10)	0.0524 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0437 (9)	0.0358 (8)	0.0712 (11)	−0.0073 (7)	−0.0243 (8)	0.0000 (8)
C2	0.0596 (12)	0.0400 (10)	0.0947 (15)	−0.0030 (8)	−0.0391 (11)	0.0001 (10)
C3	0.0565 (12)	0.0461 (11)	0.1142 (19)	0.0086 (9)	−0.0374 (12)	−0.0199 (12)
C4	0.0505 (11)	0.0595 (13)	0.0962 (17)	0.0019 (9)	−0.0117 (11)	−0.0244 (12)
C5	0.0499 (10)	0.0529 (11)	0.0731 (13)	−0.0035 (8)	−0.0046 (9)	−0.0098 (9)
C6	0.0404 (8)	0.0387 (9)	0.0618 (10)	−0.0068 (7)	−0.0107 (7)	−0.0039 (7)
C7	0.0421 (8)	0.0378 (8)	0.0510 (9)	−0.0075 (7)	−0.0056 (7)	0.0013 (7)
C8	0.0387 (8)	0.0332 (7)	0.0417 (8)	−0.0095 (6)	−0.0105 (6)	0.0011 (6)
C9	0.0428 (8)	0.0371 (8)	0.0479 (9)	−0.0112 (6)	−0.0186 (7)	0.0064 (6)
C10	0.0497 (9)	0.0415 (9)	0.0625 (11)	−0.0120 (7)	−0.0259 (8)	0.0115 (8)
C11	0.0379 (7)	0.0337 (7)	0.0350 (7)	−0.0096 (6)	−0.0086 (6)	0.0019 (6)
C12	0.0368 (7)	0.0378 (8)	0.0374 (7)	−0.0095 (6)	−0.0107 (6)	−0.0015 (6)
C13	0.0504 (9)	0.0511 (10)	0.0351 (8)	−0.0126 (8)	−0.0109 (7)	0.0002 (7)
C14	0.0559 (10)	0.0498 (10)	0.0400 (8)	−0.0161 (8)	−0.0184 (7)	0.0104 (7)
C15	0.0361 (7)	0.0371 (8)	0.0392 (8)	−0.0081 (6)	−0.0102 (6)	−0.0004 (6)
C16	0.0589 (10)	0.0446 (9)	0.0329 (8)	−0.0097 (8)	−0.0073 (7)	0.0039 (6)
C17	0.0908 (15)	0.0682 (13)	0.0444 (10)	−0.0304 (12)	−0.0208 (10)	0.0021 (9)
C18	0.173 (3)	0.0811 (18)	0.0647 (15)	−0.0454 (19)	−0.0226 (17)	−0.0155 (13)
C19	0.0333 (7)	0.0453 (9)	0.0395 (8)	−0.0044 (6)	−0.0055 (6)	−0.0059 (6)
C20	0.0400 (8)	0.0430 (8)	0.0386 (8)	−0.0065 (6)	−0.0079 (6)	−0.0011 (6)
C21	0.0465 (9)	0.0412 (9)	0.0468 (9)	−0.0034 (7)	−0.0109 (7)	−0.0057 (7)
C22	0.0423 (8)	0.0434 (9)	0.0439 (8)	−0.0153 (7)	−0.0083 (7)	−0.0019 (7)
C23	0.0532 (9)	0.0459 (9)	0.0426 (8)	−0.0237 (8)	−0.0075 (7)	−0.0013 (7)
C24	0.0672 (12)	0.0572 (11)	0.0503 (10)	−0.0154 (9)	−0.0008 (9)	−0.0049 (8)
C25	0.0807 (15)	0.0671 (14)	0.0613 (13)	−0.0206 (12)	0.0070 (11)	−0.0112 (11)
C26	0.1029 (18)	0.0818 (15)	0.0465 (10)	−0.0523 (15)	−0.0207 (11)	0.0064 (10)
C27	0.0685 (12)	0.0629 (12)	0.0505 (10)	−0.0312 (10)	−0.0166 (9)	0.0033 (9)
N1	0.0419 (7)	0.0348 (6)	0.0330 (6)	−0.0055 (5)	−0.0083 (5)	0.0013 (5)
N2	0.0373 (6)	0.0388 (7)	0.0349 (6)	−0.0040 (5)	−0.0078 (5)	−0.0020 (5)
N3	0.0441 (8)	0.0569 (9)	0.0486 (8)	−0.0131 (7)	−0.0127 (6)	−0.0051 (7)
N4	0.1033 (16)	0.0782 (13)	0.0495 (10)	−0.0441 (12)	−0.0005 (10)	−0.0073 (9)
O1	0.0647 (8)	0.0511 (8)	0.0652 (8)	−0.0048 (6)	0.0122 (6)	0.0122 (6)
O2	0.0784 (10)	0.0606 (9)	0.0739 (9)	−0.0016 (7)	−0.0277 (8)	0.0263 (7)
O3	0.0435 (6)	0.0452 (6)	0.0494 (6)	−0.0029 (5)	−0.0168 (5)	0.0054 (5)
O4	0.0367 (6)	0.0643 (8)	0.0502 (7)	−0.0081 (5)	−0.0083 (5)	−0.0125 (6)

C1—C6	1.390 (3)	C16—C17	1.493 (3)
C1—C2	1.397 (2)	C16—H16A	0.9700
C1—C10	1.479 (3)	C16—H16B	0.9700
C2—C3	1.368 (3)	C17—C18	1.300 (3)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.376 (3)	C18—H18A	0.9300
C3—H3	0.9300	C18—H18B	0.9300
C4—C5	1.382 (3)	C19—N2	1.4525 (18)
C4—H4	0.9300	C19—C20	1.511 (2)
C5—C6	1.387 (2)	C19—H19A	0.9700
C5—H5	0.9300	C19—H19B	0.9700
C6—C7	1.487 (2)	C20—O4	1.453 (2)
C7—O1	1.218 (2)	C20—C21	1.525 (2)
C7—C8	1.479 (2)	C20—H20	0.9800
C8—C11	1.397 (2)	C21—C22	1.494 (2)
C8—C9	1.415 (2)	C21—H21A	0.9700
C9—C14	1.388 (2)	C21—H21B	0.9700
C9—C10	1.482 (2)	C22—N3	1.278 (2)
C10—O2	1.220 (2)	C22—C23	1.465 (2)
C11—N1	1.3943 (19)	C23—C24	1.380 (3)
C11—C12	1.412 (2)	C23—C27	1.393 (3)
C12—C13	1.376 (2)	C24—C25	1.389 (3)
C12—N2	1.3760 (19)	C24—H24	0.9300
C13—C14	1.381 (2)	C25—N4	1.315 (3)
C13—H13	0.9300	C25—H25	0.9300
C14—H14	0.9300	C26—N4	1.326 (3)
C15—O3	1.2171 (18)	C26—C27	1.380 (3)
C15—N2	1.3726 (19)	C26—H26	0.9300
C15—N1	1.3927 (19)	C27—H27	0.9300
C16—N1	1.4621 (19)	N3—O4	1.4084 (18)
C6—C1—C2	119.35 (18)	C18—C17—C16	123.9 (2)
C6—C1—C10	120.62 (15)	C18—C17—H17	118.1
C2—C1—C10	119.92 (17)	C16—C17—H17	118.1
C3—C2—C1	120.4 (2)	C17—C18—H18A	120.0
C3—C2—H2	119.8	C17—C18—H18B	120.0
C1—C2—H2	119.8	H18A—C18—H18B	120.0
C2—C3—C4	120.29 (19)	N2—C19—C20	111.63 (12)
C2—C3—H3	119.9	N2—C19—H19A	109.3
C4—C3—H3	119.9	C20—C19—H19A	109.3
C3—C4—C5	120.2 (2)	N2—C19—H19B	109.3
C3—C4—H4	119.9	C20—C19—H19B	109.3
C5—C4—H4	119.9	H19A—C19—H19B	108.0
C4—C5—C6	120.1 (2)	O4—C20—C19	108.93 (13)
C4—C5—H5	120.0	O4—C20—C21	104.00 (12)
C6—C5—H5	120.0	C19—C20—C21	112.82 (13)
C5—C6—C1	119.71 (17)	O4—C20—H20	110.3
C5—C6—C7	118.96 (17)	C19—C20—H20	110.3
C1—C6—C7	121.30 (15)	C21—C20—H20	110.3
O1—C7—C8	121.68 (15)	C22—C21—C20	100.34 (13)
O1—C7—C6	120.30 (15)	C22—C21—H21A	111.7
C8—C7—C6	117.76 (14)	C20—C21—H21A	111.7
C11—C8—C9	116.86 (13)	C22—C21—H21B	111.7
C11—C8—C7	123.26 (14)	C20—C21—H21B	111.7
C9—C8—C7	119.39 (14)	H21A—C21—H21B	109.5
C14—C9—C8	121.33 (15)	N3—C22—C23	120.26 (16)
C14—C9—C10	117.88 (15)	N3—C22—C21	113.77 (14)
C8—C9—C10	120.79 (15)	C23—C22—C21	125.98 (15)
O2—C10—C1	120.60 (16)	C24—C23—C27	116.82 (17)
O2—C10—C9	121.25 (17)	C24—C23—C22	121.28 (17)
C1—C10—C9	118.15 (15)	C27—C23—C22	121.87 (17)
N1—C11—C8	134.04 (13)	C23—C24—C25	119.1 (2)
N1—C11—C12	106.27 (12)	C23—C24—H24	120.4
C8—C11—C12	119.68 (13)	C25—C24—H24	120.4
C13—C12—N2	129.78 (14)	N4—C25—C24	124.4 (2)
C13—C12—C11	122.57 (14)	N4—C25—H25	117.8
N2—C12—C11	107.59 (13)	C24—C25—H25	117.8
C12—C13—C14	117.41 (14)	N4—C26—C27	124.4 (2)
C12—C13—H13	121.3	N4—C26—H26	117.8
C14—C13—H13	121.3	C27—C26—H26	117.8
C13—C14—C9	121.59 (15)	C26—C27—C23	119.0 (2)
C13—C14—H14	119.2	C26—C27—H27	120.5
C9—C14—H14	119.2	C23—C27—H27	120.5
O3—C15—N2	126.58 (14)	C15—N1—C11	109.31 (12)
O3—C15—N1	126.66 (14)	C15—N1—C16	118.49 (13)
N2—C15—N1	106.75 (13)	C11—N1—C16	129.16 (13)
N1—C16—C17	111.20 (13)	C15—N2—C12	109.96 (12)
N1—C16—H16A	109.4	C15—N2—C19	122.55 (13)
C17—C16—H16A	109.4	C12—N2—C19	127.42 (13)
N1—C16—H16B	109.4	C22—N3—O4	109.39 (13)
C17—C16—H16B	109.4	C25—N4—C26	116.19 (19)
H16A—C16—H16B	108.0	N3—O4—C20	108.52 (11)
C6—C1—C2—C3	−0.5 (3)	N1—C16—C17—C18	125.5 (2)
C10—C1—C2—C3	175.79 (17)	N2—C19—C20—O4	63.70 (16)
C1—C2—C3—C4	−0.7 (3)	N2—C19—C20—C21	178.64 (13)
C2—C3—C4—C5	1.0 (3)	O4—C20—C21—C22	18.17 (16)
C3—C4—C5—C6	−0.1 (3)	C19—C20—C21—C22	−99.71 (15)
C4—C5—C6—C1	−1.1 (3)	C20—C21—C22—N3	−12.02 (19)
C4—C5—C6—C7	−179.20 (18)	C20—C21—C22—C23	168.07 (15)
C2—C1—C6—C5	1.4 (3)	N3—C22—C23—C24	−173.79 (16)
C10—C1—C6—C5	−174.83 (17)	C21—C22—C23—C24	6.1 (3)
C2—C1—C6—C7	179.42 (16)	N3—C22—C23—C27	8.2 (3)
C10—C1—C6—C7	3.2 (3)	C21—C22—C23—C27	−171.93 (16)
C5—C6—C7—O1	11.5 (3)	C27—C23—C24—C25	1.2 (3)
C1—C6—C7—O1	−166.50 (18)	C22—C23—C24—C25	−176.92 (17)
C5—C6—C7—C8	−174.24 (16)	C23—C24—C25—N4	0.0 (3)
C1—C6—C7—C8	7.7 (2)	N4—C26—C27—C23	0.3 (3)
O1—C7—C8—C11	−13.9 (3)	C24—C23—C27—C26	−1.4 (3)
C6—C7—C8—C11	171.97 (15)	C22—C23—C27—C26	176.75 (16)
O1—C7—C8—C9	157.86 (17)	O3—C15—N1—C11	176.95 (15)
C6—C7—C8—C9	−16.3 (2)	N2—C15—N1—C11	−2.11 (16)
C11—C8—C9—C14	6.1 (2)	O3—C15—N1—C16	14.9 (2)
C7—C8—C9—C14	−166.19 (15)	N2—C15—N1—C16	−164.21 (13)
C11—C8—C9—C10	−173.72 (14)	C8—C11—N1—C15	178.90 (16)
C7—C8—C9—C10	14.0 (2)	C12—C11—N1—C15	−0.01 (16)
C6—C1—C10—O2	174.24 (18)	C8—C11—N1—C16	−21.5 (3)
C2—C1—C10—O2	−2.0 (3)	C12—C11—N1—C16	159.59 (15)
C6—C1—C10—C9	−5.8 (2)	C17—C16—N1—C15	99.02 (18)
C2—C1—C10—C9	178.01 (15)	C17—C16—N1—C11	−59.0 (2)
C14—C9—C10—O2	−2.8 (3)	O3—C15—N2—C12	−175.56 (15)
C8—C9—C10—O2	176.99 (16)	N1—C15—N2—C12	3.51 (17)
C14—C9—C10—C1	177.19 (15)	O3—C15—N2—C19	7.3 (2)
C8—C9—C10—C1	−3.0 (2)	N1—C15—N2—C19	−173.60 (13)
C9—C8—C11—N1	172.45 (16)	C13—C12—N2—C15	173.53 (16)
C7—C8—C11—N1	−15.6 (3)	C11—C12—N2—C15	−3.55 (17)
C9—C8—C11—C12	−8.8 (2)	C13—C12—N2—C19	−9.5 (3)
C7—C8—C11—C12	163.18 (14)	C11—C12—N2—C19	173.38 (13)
N1—C11—C12—C13	−175.20 (14)	C20—C19—N2—C15	78.33 (18)
C8—C11—C12—C13	5.7 (2)	C20—C19—N2—C12	−98.24 (18)
N1—C11—C12—N2	2.14 (16)	C23—C22—N3—O4	−179.88 (13)
C8—C11—C12—N2	−176.96 (13)	C21—C22—N3—O4	0.2 (2)
N2—C12—C13—C14	−176.07 (16)	C24—C25—N4—C26	−1.1 (3)
C11—C12—C13—C14	0.6 (2)	C27—C26—N4—C25	1.0 (3)
C12—C13—C14—C9	−3.5 (3)	C22—N3—O4—C20	12.78 (18)
C8—C9—C14—C13	0.1 (3)	C19—C20—O4—N3	100.89 (14)
C10—C9—C14—C13	179.91 (15)	C21—C20—O4—N3	−19.64 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N3i	0.93	2.58	3.471 (2)	160
C3—H3···O4i	0.93	2.67	3.470 (2)	145
C19—H19A···O3ii	0.97	2.56	3.3356 (19)	137
C21—H21A···O3ii	0.97	2.45	3.350 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N3i	0.93	2.58	3.471 (2)	160
C3—H3⋯O4i	0.93	2.67	3.470 (2)	145
C19—H19A⋯O3ii	0.97	2.56	3.3356 (19)	137
C21—H21A⋯O3ii	0.97	2.45	3.350 (2)	154

Symmetry codes: (i) ; (ii) .