Diethyl 6,13-dioxo-5,7,12,13b,13c,14-hexa-hydro-6H,13H-5a,6a,12a,13a-tetra-azabenz[5,6]azuleno[2,1,8-ija]benz[f]azulene-13b,13c-dicarboxyl-ate 1,2-dichloro-ethane solvate.

In the title inclusion compound, C(26)H(26)N(4)O(6)·C(2)H(4)Cl(2), the solvent mol-ecule occupies a cavity inside the clip-type mol-ecule which is based on the glycoluril skeleton with two ethyl acetate substituents on the convex face of the glycoluril system. The dihedral angle between the aromatic rings of the host is 43.59 (4)° and the centroid-centroid distance is 6.741 (5) Å. The 1,2-dichloro-etane mol-ecule adopts a gauche conformation enabling it to participate in C-H⋯π inter-actions with the host. The packing motif in the title compound differs from that observed in the crystal structures of the host and in the benzene solvate. The host mol-ecules are linked into tapes by π-π stacking inter-actions (centroid-centroid distance = 3.733 Å) and are further assembled into layers via C-H⋯O inter-actions. One of the ethyl groups is disorded over two positions with site-occupancy factors of 0.702 (14) and 0.298 (14).

Related literature

For the related structures, see: Chen et al. (2007 ▶); Hof et al.,(2002 ▶); Hu et al. (2007 ▶); Isaacs & Fettinger (1999 ▶); Wang et al. (2006 ▶).

Experimental

Crystal data

C26H26N4O6·C2H4Cl2

M = 589.46

Triclinic,

a = 8.9468 (10) Å

b = 11.1544 (13) Å

c = 15.6260 (18) Å

α = 69.257 (2)°

β = 82.688 (2)°

γ = 76.892 (2)°

V = 1418.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 292 K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

10171 measured reflections

4947 independent reflections

4056 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.188

S = 1.04

4947 reflections

383 parameters

28 restraints

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.64 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809041373/gk2232sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041373/gk2232Isup2.hkl

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

C26H26N4O6·C2H4Cl2	Z = 2
Mr = 589.46	F(000) = 616
Triclinic, P1	Dx = 1.380 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9468 (10) Å	Cell parameters from 5260 reflections
b = 11.1544 (13) Å	θ = 2.3–26.1°
c = 15.6260 (18) Å	µ = 0.28 mm−1
α = 69.257 (2)°	T = 292 K
β = 82.688 (2)°	Block, colorless
γ = 76.892 (2)°	0.30 × 0.20 × 0.10 mm
V = 1418.5 (3) Å3

Bruker SMART CCD area-detector diffractometer	4056 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
graphite	θmax = 25.0°, θmin = 2.0°
φ and ω scans	h = −10→10
10171 measured reflections	k = −13→13
4947 independent reflections	l = −18→18

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.1032P)2 + 0.8923P] where P = (Fo2 + 2Fc2)/3
4947 reflections	(Δ/σ)max = 0.001
383 parameters	Δρmax = 0.69 e Å−3
28 restraints	Δρmin = −0.64 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	Occ. (<1)
C1	0.3563 (3)	0.4517 (3)	0.43467 (17)	0.0419 (6)
C2	0.4101 (3)	0.3329 (3)	0.5006 (2)	0.0527 (7)
H2	0.3424	0.2944	0.5472	0.063*
C3	0.5627 (4)	0.2702 (3)	0.4988 (2)	0.0585 (8)
H3	0.5962	0.1900	0.5434	0.070*
C4	0.6644 (3)	0.3268 (3)	0.4308 (2)	0.0558 (8)
H4	0.7670	0.2856	0.4294	0.067*
C5	0.6127 (3)	0.4452 (3)	0.3650 (2)	0.0489 (7)
H5	0.6816	0.4833	0.3191	0.059*
C6	0.4600 (3)	0.5090 (3)	0.36552 (18)	0.0418 (6)
C7	0.4116 (3)	0.6394 (3)	0.29185 (19)	0.0477 (7)
H7A	0.3833	0.7071	0.3197	0.057*
H7B	0.4982	0.6589	0.2487	0.057*
C8	0.1895 (3)	0.5177 (3)	0.44266 (18)	0.0453 (6)
H8A	0.1394	0.4605	0.4949	0.054*
H8B	0.1866	0.5974	0.4552	0.054*
C9	0.2946 (3)	0.6387 (2)	0.15541 (18)	0.0398 (6)
C10	0.0566 (3)	0.4531 (2)	0.34105 (17)	0.0372 (6)
C11	0.1265 (3)	0.6567 (2)	0.27998 (17)	0.0378 (6)
C12	0.0736 (3)	0.7930 (3)	0.2899 (2)	0.0508 (7)
C14	−0.0459 (15)	0.9472 (8)	0.4212 (6)	0.128 (4)	0.702 (14)
H14A	−0.0458	0.8751	0.4776	0.192*	0.702 (14)
H14B	−0.0985	1.0265	0.4314	0.192*	0.702 (14)
H14C	0.0581	0.9543	0.3994	0.192*	0.702 (14)
C13	−0.1260 (11)	0.9249 (6)	0.3514 (6)	0.095 (3)	0.702 (14)
H13A	−0.2332	0.9230	0.3705	0.114*	0.702 (14)
H13B	−0.1203	0.9933	0.2925	0.114*	0.702 (14)
C15	0.0392 (3)	0.6362 (2)	0.20652 (16)	0.0368 (5)
C16	−0.1181 (3)	0.7301 (3)	0.18476 (19)	0.0444 (6)
C17	−0.2468 (4)	0.9420 (3)	0.1062 (3)	0.0680 (9)
H17A	−0.3236	0.9100	0.0863	0.082*
H17B	−0.2870	0.9616	0.1614	0.082*
C18	−0.2110 (6)	1.0594 (4)	0.0345 (3)	0.0979 (15)
H18A	−0.1399	1.0935	0.0562	0.147*
H18B	−0.3036	1.1239	0.0187	0.147*
H18C	−0.1658	1.0379	−0.0187	0.147*
C19	−0.0402 (3)	0.4324 (3)	0.20547 (18)	0.0429 (6)
H19A	−0.1262	0.4892	0.1699	0.052*
H19B	−0.0778	0.3591	0.2512	0.052*
C20	0.1259 (3)	0.6119 (3)	0.05267 (17)	0.0428 (6)
H20A	0.1919	0.6513	0.0009	0.051*
H20B	0.0205	0.6467	0.0350	0.051*
C21	0.0802 (3)	0.3813 (3)	0.14224 (17)	0.0419 (6)
C22	0.1590 (3)	0.4658 (3)	0.07154 (17)	0.0406 (6)
C23	0.2683 (3)	0.4133 (3)	0.01628 (19)	0.0493 (7)
H23	0.3224	0.4681	−0.0301	0.059*
C24	0.2981 (4)	0.2818 (3)	0.0286 (2)	0.0550 (7)
H24	0.3710	0.2487	−0.0095	0.066*
C25	0.2200 (4)	0.1994 (3)	0.0975 (2)	0.0572 (8)
H25	0.2394	0.1106	0.1059	0.069*
C26	0.1127 (3)	0.2490 (3)	0.1541 (2)	0.0497 (7)
H26	0.0611	0.1927	0.2011	0.060*
C27	0.4248 (6)	0.1793 (8)	0.3161 (4)	0.130 (2)
H27A	0.3189	0.2096	0.3335	0.156*
H27B	0.4875	0.1658	0.3663	0.156*
C28	0.4742 (5)	0.2807 (4)	0.2334 (4)	0.0969 (16)
H28A	0.4497	0.3640	0.2436	0.116*
H28B	0.4169	0.2891	0.1822	0.116*
Cl1	0.4405 (2)	0.03136 (15)	0.29818 (12)	0.1337 (6)
Cl2	0.67477 (15)	0.24467 (12)	0.20429 (9)	0.0987 (4)
N1	0.2825 (2)	0.6424 (2)	0.24224 (15)	0.0421 (5)
N2	0.1009 (2)	0.5506 (2)	0.36207 (14)	0.0387 (5)
N3	0.1477 (2)	0.6518 (2)	0.12931 (13)	0.0373 (5)
N4	0.0168 (2)	0.5040 (2)	0.25176 (14)	0.0392 (5)
O1	0.4116 (2)	0.6274 (2)	0.10852 (13)	0.0527 (5)
O2	0.0510 (2)	0.34424 (19)	0.39298 (13)	0.0516 (5)
O3	0.1344 (3)	0.8818 (2)	0.2469 (2)	0.0853 (8)
O4	−0.0449 (3)	0.7988 (2)	0.3460 (2)	0.0856 (8)
O5	−0.2343 (3)	0.7010 (3)	0.2211 (2)	0.0865 (9)
O6	−0.1047 (2)	0.84312 (19)	0.12437 (15)	0.0582 (6)
C14'	−0.178 (2)	0.9307 (14)	0.4359 (10)	0.083 (6)	0.298 (14)
H14D	−0.2692	0.9053	0.4272	0.125*	0.298 (14)
H14E	−0.2036	1.0188	0.4364	0.125*	0.298 (14)
H14F	−0.1368	0.8732	0.4933	0.125*	0.298 (14)
C13'	−0.062 (3)	0.9224 (17)	0.3593 (19)	0.109 (9)	0.298 (14)
H13C	−0.0937	0.9929	0.3033	0.131*	0.298 (14)
H13D	0.0366	0.9318	0.3737	0.131*	0.298 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0371 (13)	0.0563 (16)	0.0361 (13)	−0.0142 (11)	−0.0003 (10)	−0.0176 (12)
C2	0.0476 (16)	0.0627 (18)	0.0445 (15)	−0.0184 (13)	−0.0048 (12)	−0.0086 (13)
C3	0.0564 (19)	0.0537 (17)	0.0596 (18)	−0.0080 (14)	−0.0156 (15)	−0.0096 (14)
C4	0.0385 (15)	0.0658 (19)	0.068 (2)	−0.0054 (13)	−0.0085 (14)	−0.0292 (16)
C5	0.0338 (14)	0.0666 (18)	0.0494 (16)	−0.0145 (12)	0.0019 (12)	−0.0218 (14)
C6	0.0354 (13)	0.0540 (15)	0.0411 (14)	−0.0148 (11)	−0.0013 (11)	−0.0187 (12)
C7	0.0353 (14)	0.0592 (17)	0.0485 (15)	−0.0192 (12)	−0.0022 (11)	−0.0118 (13)
C8	0.0372 (14)	0.0653 (17)	0.0349 (13)	−0.0139 (12)	0.0024 (11)	−0.0176 (12)
C9	0.0352 (13)	0.0367 (13)	0.0410 (14)	−0.0095 (10)	0.0016 (11)	−0.0049 (10)
C10	0.0270 (12)	0.0450 (14)	0.0365 (13)	−0.0094 (10)	0.0044 (10)	−0.0105 (11)
C11	0.0305 (12)	0.0421 (13)	0.0402 (13)	−0.0094 (10)	0.0005 (10)	−0.0123 (11)
C12	0.0506 (17)	0.0498 (16)	0.0552 (17)	−0.0114 (13)	−0.0061 (14)	−0.0194 (14)
C14	0.196 (11)	0.081 (5)	0.103 (6)	0.005 (6)	−0.015 (6)	−0.044 (4)
C13	0.089 (5)	0.063 (4)	0.115 (5)	0.019 (3)	0.020 (4)	−0.036 (3)
C15	0.0323 (12)	0.0401 (13)	0.0359 (13)	−0.0097 (10)	0.0002 (10)	−0.0094 (10)
C16	0.0347 (14)	0.0491 (15)	0.0466 (15)	−0.0094 (11)	−0.0008 (11)	−0.0125 (12)
C17	0.0547 (19)	0.0559 (19)	0.076 (2)	0.0096 (15)	−0.0052 (16)	−0.0134 (16)
C18	0.099 (3)	0.054 (2)	0.103 (3)	0.013 (2)	0.000 (3)	0.000 (2)
C19	0.0405 (14)	0.0486 (15)	0.0423 (14)	−0.0183 (11)	0.0012 (11)	−0.0136 (12)
C20	0.0441 (14)	0.0478 (15)	0.0330 (13)	−0.0109 (11)	−0.0008 (11)	−0.0085 (11)
C21	0.0398 (14)	0.0502 (15)	0.0383 (13)	−0.0132 (11)	−0.0062 (11)	−0.0140 (11)
C22	0.0378 (13)	0.0494 (15)	0.0353 (13)	−0.0096 (11)	−0.0032 (10)	−0.0140 (11)
C23	0.0454 (15)	0.0612 (18)	0.0432 (15)	−0.0137 (13)	0.0013 (12)	−0.0189 (13)
C24	0.0495 (17)	0.0634 (19)	0.0596 (18)	−0.0066 (14)	0.0005 (14)	−0.0337 (15)
C25	0.0621 (19)	0.0514 (17)	0.0642 (19)	−0.0075 (14)	−0.0086 (15)	−0.0272 (15)
C26	0.0543 (17)	0.0487 (16)	0.0494 (16)	−0.0181 (13)	−0.0049 (13)	−0.0146 (13)
C27	0.073 (3)	0.229 (8)	0.118 (4)	−0.017 (4)	0.000 (3)	−0.105 (5)
C28	0.089 (3)	0.066 (2)	0.145 (4)	0.007 (2)	−0.055 (3)	−0.044 (3)
Cl1	0.1401 (13)	0.1025 (10)	0.1312 (12)	−0.0443 (9)	−0.0254 (10)	0.0126 (8)
Cl2	0.1068 (9)	0.0891 (8)	0.1020 (8)	−0.0310 (6)	0.0009 (7)	−0.0292 (6)
N1	0.0317 (11)	0.0554 (13)	0.0394 (12)	−0.0153 (9)	0.0016 (9)	−0.0134 (10)
N2	0.0312 (11)	0.0488 (12)	0.0351 (11)	−0.0116 (9)	0.0020 (8)	−0.0119 (9)
N3	0.0331 (11)	0.0408 (11)	0.0344 (11)	−0.0087 (8)	0.0027 (8)	−0.0090 (9)
N4	0.0401 (11)	0.0413 (11)	0.0369 (11)	−0.0146 (9)	0.0001 (9)	−0.0107 (9)
O1	0.0362 (10)	0.0659 (13)	0.0494 (11)	−0.0124 (9)	0.0105 (9)	−0.0143 (9)
O2	0.0540 (12)	0.0500 (11)	0.0436 (11)	−0.0175 (9)	−0.0005 (9)	−0.0034 (9)
O3	0.106 (2)	0.0513 (14)	0.101 (2)	−0.0313 (14)	0.0131 (17)	−0.0258 (14)
O4	0.0864 (18)	0.0585 (14)	0.101 (2)	−0.0014 (13)	0.0328 (16)	−0.0346 (14)
O5	0.0343 (12)	0.0731 (16)	0.119 (2)	−0.0072 (10)	0.0087 (13)	0.0011 (15)
O6	0.0463 (11)	0.0451 (11)	0.0637 (13)	0.0029 (9)	0.0031 (9)	−0.0041 (10)
C14'	0.103 (11)	0.060 (7)	0.082 (9)	0.005 (7)	−0.001 (8)	−0.031 (6)
C13'	0.102 (12)	0.102 (11)	0.117 (12)	−0.003 (8)	0.006 (9)	−0.044 (8)

C1—C2	1.385 (4)	C16—O6	1.300 (3)
C1—C6	1.401 (4)	C17—C18	1.460 (5)
C1—C8	1.518 (4)	C17—O6	1.465 (4)
C2—C3	1.388 (4)	C17—H17A	0.9700
C2—H2	0.9300	C17—H17B	0.9700
C3—C4	1.377 (5)	C18—H18A	0.9600
C3—H3	0.9300	C18—H18B	0.9600
C4—C5	1.377 (4)	C18—H18C	0.9600
C4—H4	0.9300	C19—N4	1.453 (3)
C5—C6	1.391 (4)	C19—C21	1.520 (4)
C5—H5	0.9300	C19—H19A	0.9700
C6—C7	1.511 (4)	C19—H19B	0.9700
C7—N1	1.459 (3)	C20—N3	1.466 (3)
C7—H7A	0.9700	C20—C22	1.515 (4)
C7—H7B	0.9700	C20—H20A	0.9700
C8—N2	1.464 (3)	C20—H20B	0.9700
C8—H8A	0.9700	C21—C26	1.387 (4)
C8—H8B	0.9700	C21—C22	1.403 (4)
C9—O1	1.208 (3)	C22—C23	1.389 (4)
C9—N1	1.362 (3)	C23—C24	1.376 (4)
C9—N3	1.386 (3)	C23—H23	0.9300
C10—O2	1.206 (3)	C24—C25	1.375 (5)
C10—N4	1.367 (3)	C24—H24	0.9300
C10—N2	1.389 (3)	C25—C26	1.378 (4)
C11—N2	1.439 (3)	C25—H25	0.9300
C11—N1	1.441 (3)	C26—H26	0.9300
C11—C12	1.543 (4)	C27—C28	1.480 (8)
C11—C15	1.573 (3)	C27—Cl1	1.742 (7)
C12—O3	1.186 (4)	C27—H27A	0.9700
C12—O4	1.292 (4)	C27—H27B	0.9700
C14—C13	1.496 (8)	C28—Cl2	1.784 (5)
C14—H14A	0.9600	C28—H28A	0.9700
C14—H14B	0.9600	C28—H28B	0.9700
C14—H14C	0.9600	O4—C13'	1.438 (9)
C13—O4	1.455 (5)	C14'—C13'	1.500 (9)
C13—H13A	0.9700	C14'—H14D	0.9600
C13—H13B	0.9700	C14'—H14E	0.9600
C15—N3	1.435 (3)	C14'—H14F	0.9600
C15—N4	1.440 (3)	C13'—H13C	0.9700
C15—C16	1.547 (4)	C13'—H13D	0.9700
C16—O5	1.175 (3)
C2—C1—C6	118.6 (3)	H18B—C18—H18C	109.5
C2—C1—C8	118.8 (2)	N4—C19—C21	113.5 (2)
C6—C1—C8	122.5 (2)	N4—C19—H19A	108.9
C1—C2—C3	121.4 (3)	C21—C19—H19A	108.9
C1—C2—H2	119.3	N4—C19—H19B	108.9
C3—C2—H2	119.3	C21—C19—H19B	108.9
C4—C3—C2	119.8 (3)	H19A—C19—H19B	107.7
C4—C3—H3	120.1	N3—C20—C22	115.3 (2)
C2—C3—H3	120.1	N3—C20—H20A	108.4
C3—C4—C5	119.3 (3)	C22—C20—H20A	108.4
C3—C4—H4	120.3	N3—C20—H20B	108.4
C5—C4—H4	120.3	C22—C20—H20B	108.4
C4—C5—C6	121.6 (3)	H20A—C20—H20B	107.5
C4—C5—H5	119.2	C26—C21—C22	119.2 (3)
C6—C5—H5	119.2	C26—C21—C19	119.6 (2)
C5—C6—C1	119.2 (3)	C22—C21—C19	121.3 (2)
C5—C6—C7	118.8 (2)	C23—C22—C21	118.6 (3)
C1—C6—C7	122.0 (2)	C23—C22—C20	119.3 (2)
N1—C7—C6	112.8 (2)	C21—C22—C20	122.1 (2)
N1—C7—H7A	109.0	C24—C23—C22	121.4 (3)
C6—C7—H7A	109.0	C24—C23—H23	119.3
N1—C7—H7B	109.0	C22—C23—H23	119.3
C6—C7—H7B	109.0	C25—C24—C23	119.9 (3)
H7A—C7—H7B	107.8	C25—C24—H24	120.0
N2—C8—C1	115.4 (2)	C23—C24—H24	120.0
N2—C8—H8A	108.4	C24—C25—C26	119.7 (3)
C1—C8—H8A	108.4	C24—C25—H25	120.1
N2—C8—H8B	108.4	C26—C25—H25	120.1
C1—C8—H8B	108.4	C25—C26—C21	121.2 (3)
H8A—C8—H8B	107.5	C25—C26—H26	119.4
O1—C9—N1	126.6 (2)	C21—C26—H26	119.4
O1—C9—N3	125.6 (2)	C28—C27—Cl1	112.0 (4)
N1—C9—N3	107.8 (2)	C28—C27—H27A	109.2
O2—C10—N4	126.3 (2)	Cl1—C27—H27A	109.2
O2—C10—N2	126.0 (2)	C28—C27—H27B	109.2
N4—C10—N2	107.6 (2)	Cl1—C27—H27B	109.2
N2—C11—N1	113.7 (2)	H27A—C27—H27B	107.9
N2—C11—C12	113.9 (2)	C27—C28—Cl2	112.9 (3)
N1—C11—C12	110.0 (2)	C27—C28—H28A	109.0
N2—C11—C15	103.24 (19)	Cl2—C28—H28A	109.0
N1—C11—C15	101.53 (19)	C27—C28—H28B	109.0
C12—C11—C15	113.7 (2)	Cl2—C28—H28B	109.0
O3—C12—O4	125.4 (3)	H28A—C28—H28B	107.8
O3—C12—C11	122.0 (3)	C9—N1—C11	113.3 (2)
O4—C12—C11	112.6 (2)	C9—N1—C7	124.3 (2)
O4—C13—C14	105.1 (6)	C11—N1—C7	122.2 (2)
O4—C13—H13A	110.7	C10—N2—C11	110.7 (2)
C14—C13—H13A	110.7	C10—N2—C8	120.4 (2)
O4—C13—H13B	110.7	C11—N2—C8	120.6 (2)
C14—C13—H13B	110.7	C9—N3—C15	111.0 (2)
H13A—C13—H13B	108.8	C9—N3—C20	120.1 (2)
N3—C15—N4	114.1 (2)	C15—N3—C20	120.6 (2)
N3—C15—C16	113.7 (2)	C10—N4—C15	113.5 (2)
N4—C15—C16	109.9 (2)	C10—N4—C19	123.9 (2)
N3—C15—C11	103.08 (18)	C15—N4—C19	122.6 (2)
N4—C15—C11	101.56 (19)	C12—O4—C13'	105.1 (7)
C16—C15—C11	113.7 (2)	C12—O4—C13	119.7 (5)
O5—C16—O6	125.1 (3)	C13'—O4—C13	23.8 (11)
O5—C16—C15	122.6 (3)	C16—O6—C17	115.7 (2)
O6—C16—C15	112.2 (2)	C13'—C14'—H14D	109.5
C18—C17—O6	107.9 (3)	C13'—C14'—H14E	109.5
C18—C17—H17A	110.1	H14D—C14'—H14E	109.5
O6—C17—H17A	110.1	C13'—C14'—H14F	109.5
C18—C17—H17B	110.1	H14D—C14'—H14F	109.5
O6—C17—H17B	110.1	H14E—C14'—H14F	109.5
H17A—C17—H17B	108.4	O4—C13'—C14'	110.2 (11)
C17—C18—H18A	109.5	O4—C13'—H13C	109.6
C17—C18—H18B	109.5	C14'—C13'—H13C	109.6
H18A—C18—H18B	109.5	O4—C13'—H13D	109.6
C17—C18—H18C	109.5	C14'—C13'—H13D	109.6
H18A—C18—H18C	109.5	H13C—C13'—H13D	108.1
C6—C1—C2—C3	−0.6 (4)	N2—C11—N1—C9	120.0 (2)
C8—C1—C2—C3	−177.7 (3)	C12—C11—N1—C9	−110.9 (2)
C1—C2—C3—C4	0.7 (5)	C15—C11—N1—C9	9.8 (3)
C2—C3—C4—C5	−0.4 (5)	N2—C11—N1—C7	−63.1 (3)
C3—C4—C5—C6	0.1 (5)	C12—C11—N1—C7	66.1 (3)
C4—C5—C6—C1	0.0 (4)	C15—C11—N1—C7	−173.2 (2)
C4—C5—C6—C7	179.3 (3)	C6—C7—N1—C9	−105.6 (3)
C2—C1—C6—C5	0.3 (4)	C6—C7—N1—C11	77.8 (3)
C8—C1—C6—C5	177.2 (2)	O2—C10—N2—C11	167.3 (2)
C2—C1—C6—C7	−179.0 (3)	N4—C10—N2—C11	−14.3 (3)
C8—C1—C6—C7	−2.0 (4)	O2—C10—N2—C8	18.7 (4)
C5—C6—C7—N1	125.7 (3)	N4—C10—N2—C8	−162.9 (2)
C1—C6—C7—N1	−55.0 (4)	N1—C11—N2—C10	−90.4 (2)
C2—C1—C8—N2	−125.1 (3)	C12—C11—N2—C10	142.5 (2)
C6—C1—C8—N2	57.9 (4)	C15—C11—N2—C10	18.7 (2)
N2—C11—C12—O3	150.2 (3)	N1—C11—N2—C8	58.1 (3)
N1—C11—C12—O3	21.2 (4)	C12—C11—N2—C8	−69.0 (3)
C15—C11—C12—O3	−91.9 (3)	C15—C11—N2—C8	167.2 (2)
N2—C11—C12—O4	−32.4 (3)	C1—C8—N2—C10	72.8 (3)
N1—C11—C12—O4	−161.4 (3)	C1—C8—N2—C11	−72.7 (3)
C15—C11—C12—O4	85.6 (3)	O1—C9—N3—C15	168.2 (2)
N2—C11—C15—N3	−134.01 (19)	N1—C9—N3—C15	−12.5 (3)
N1—C11—C15—N3	−16.0 (2)	O1—C9—N3—C20	19.6 (4)
C12—C11—C15—N3	102.1 (2)	N1—C9—N3—C20	−161.1 (2)
N2—C11—C15—N4	−15.6 (2)	N4—C15—N3—C9	−91.4 (2)
N1—C11—C15—N4	102.4 (2)	C16—C15—N3—C9	141.5 (2)
C12—C11—C15—N4	−139.5 (2)	C11—C15—N3—C9	17.9 (3)
N2—C11—C15—C16	102.4 (2)	N4—C15—N3—C20	57.1 (3)
N1—C11—C15—C16	−139.6 (2)	C16—C15—N3—C20	−70.1 (3)
C12—C11—C15—C16	−21.5 (3)	C11—C15—N3—C20	166.3 (2)
N3—C15—C16—O5	147.3 (3)	C22—C20—N3—C9	71.6 (3)
N4—C15—C16—O5	18.0 (4)	C22—C20—N3—C15	−74.0 (3)
C11—C15—C16—O5	−95.1 (3)	O2—C10—N4—C15	−178.7 (2)
N3—C15—C16—O6	−34.2 (3)	N2—C10—N4—C15	2.9 (3)
N4—C15—C16—O6	−163.5 (2)	O2—C10—N4—C19	0.3 (4)
C11—C15—C16—O6	83.4 (3)	N2—C10—N4—C19	−178.1 (2)
N4—C19—C21—C26	124.3 (3)	N3—C15—N4—C10	118.4 (2)
N4—C19—C21—C22	−56.0 (3)	C16—C15—N4—C10	−112.5 (2)
C26—C21—C22—C23	−0.7 (4)	C11—C15—N4—C10	8.3 (3)
C19—C21—C22—C23	179.7 (2)	N3—C15—N4—C19	−60.6 (3)
C26—C21—C22—C20	178.0 (2)	C16—C15—N4—C19	68.5 (3)
C19—C21—C22—C20	−1.6 (4)	C11—C15—N4—C19	−170.8 (2)
N3—C20—C22—C23	−122.5 (3)	C21—C19—N4—C10	−102.0 (3)
N3—C20—C22—C21	58.8 (3)	C21—C19—N4—C15	76.9 (3)
C21—C22—C23—C24	1.2 (4)	O3—C12—O4—C13'	−12.5 (15)
C20—C22—C23—C24	−177.6 (3)	C11—C12—O4—C13'	170.2 (14)
C22—C23—C24—C25	−0.7 (4)	O3—C12—O4—C13	8.0 (7)
C23—C24—C25—C26	−0.4 (5)	C11—C12—O4—C13	−169.3 (5)
C24—C25—C26—C21	0.8 (4)	C14—C13—O4—C12	−88.2 (9)
C22—C21—C26—C25	−0.3 (4)	C14—C13—O4—C13'	−32 (3)
C19—C21—C26—C25	179.3 (3)	O5—C16—O6—C17	4.0 (5)
Cl1—C27—C28—Cl2	−66.8 (4)	C15—C16—O6—C17	−174.5 (3)
O1—C9—N1—C11	−180.0 (2)	C18—C17—O6—C16	−177.6 (3)
N3—C9—N1—C11	0.7 (3)	C12—O4—C13'—C14'	−170.1 (18)
O1—C9—N1—C7	3.2 (4)	C13—O4—C13'—C14'	58.7 (18)
N3—C9—N1—C7	−176.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28B···Cg2	0.97	2.55	3.476 (3)	160
C5—H5···O5i	0.93	2.59	3.393 (4)	145
C7—H7B···O5i	0.97	2.50	3.359 (3)	148
C14—H14A···O2ii	0.96	2.57	3.514 (9)	168
C14'—H14F···O2ii	0.96	2.47	3.351 (6)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28B⋯Cg2	0.97	2.55	3.476 (3)	160
C5—H5⋯O5i	0.93	2.59	3.393 (4)	145
C7—H7B⋯O5i	0.97	2.50	3.359 (3)	148
C14—H14A⋯O2ii	0.96	2.57	3.514 (9)	168
C14′—H14F⋯O2ii	0.96	2.47	3.351 (6)	153

Symmetry codes: (i) ; (ii) . Cg2 is the centroid of the C21–C26 ring.