Diethyl 2,6-dicyclo­hexyl-4,8-dioxo-2,2,3,6,7-tetra­hydro-1H,5H-2,3a,4a,6,7a,8a-hexa­azacyclo­penta­[def]fluorene-8b,8c-dicarboxyl­ate

In the title compound, C₂₆H₄₀N₆O₆, the five-membered rings adopt envelope conformations and the six-membered rings are in chair conformations. The crystal packing is stabilized by C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.065
• wR factor = 0.188
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.97 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.55 Ratio

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O6     -   C17     ..       6.18 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C13    -   C14     ..       5.42 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C24
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C13    -   C14    ...       1.41 Ang.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C17    -   C18    ...       1.41 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H19A   ..  H26B    ..       1.91 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H20B   ..  H22A    ..       1.93 Ang.

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  12 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

S1. Comment

In current coordination and supramolecular chemistry, the rational design of coordination architectures represents one of the most exciting and rapidly developing fields, owing to their potential as functional materials (Braga et al., 1998). Glycoluril derivatives have applications in many areas, such as explosives, slow-release fertilizers, crosslinkers, iodogens, stabilizers of organic compounds against photodegradation, and reagents in combinatorial chemistry (Wu et al., 2002). Herein, we present the structure of the title compound, (I) (Fig. 1), as a continuation of our previous studies in this area (Li & Wu, 2005).

The molecule of (I) exhibits normal geometric parameters (Table 1), except for shortened C—C distances in the ethyl groups. The imidazolidine rings adopt envelope conformations, whereas, the cyclohexane and triazinane rings are in chair conformations. The crystal packing is stabilized by C—H···O hydrogen bonds (Fig. 2 and Table 2).

S2. Experimental

Cyclohexylamine (0.99 g, 10 mmol) and formaldehyde (1.2 g, 40 mmol) were added to a stirred solution of diethyl 2,5-dioxotetrahydroimidazo[4,5-d]imidazole-3a,6a-dicarboxylate (1.43 g, 5 mmol) in acetonitrile (50 ml) under a nitrogen atmosphere. The mixture was stirred overnight at room temperature. The solvent was evaporated and the compound was purified by column chromatography to yield (I) (2.40 g, 90%) as a colourless solid. Colourless block-like crystals of (I) suitable for X-ray data collection were obtained by slow evaporation of an acetic acid–ethyl acetate solution at 283 K.

S3. Refinement

Methyl H atoms were constrained to an ideal geometry, with C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C), but each group was allowed to rotate freely about its C—C bond. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.97 or 0.98 Å and U_iso(H) = 1.2U_eq(C). As attempts to restrain the C13—C14 and C17—C18 bond distances of the ethyl groups to 1.53 (1) Å resulted in limited improvement [1.444 (6) and 1.450 (6) Å, respectively], the restraints were not used. Also, no suitable disorder model was found for the ethyl groups.

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. A view of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal packing of (I). Dashed lines indicate hydrogen bonds. Atoms labeled with the suffixes `a' and `b' are generated by the symmetry codes (−x, 1 − y, 1 − z) and (x − 1, y, z), respectively.

Diethyl 2,6-dicyclohexyl-4,8-dioxo-22,3,6,7-tetrahydro-1H,5H-2,3a,4a,6,7a,8a- hexaazacyclopenta[def]fluorene-8 b,8c-dicarboxylate

Crystal data

C26H40N6O6	Z = 2
Mr = 532.64	F(000) = 572
Triclinic, P1	Dx = 1.305 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9337 (8) Å	Cell parameters from 1576 reflections
b = 13.0996 (13) Å	θ = 2.4–21.5°
c = 13.9361 (14) Å	µ = 0.09 mm^−1
α = 78.913 (2)°	T = 292 K
β = 79.686 (2)°	Plate, colorless
γ = 74.259 (2)°	0.40 × 0.18 × 0.08 mm
V = 1355.6 (2) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	4685 independent reflections
Radiation source: fine-focus sealed tube	3120 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
ϕ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −9→9
Tmin = 0.963, Tmax = 0.993	k = −15→15
6851 measured reflections	l = −16→8

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.188	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0926P)^2 + 0.2271P] where P = (Fo^2 + 2Fc^2)/3
4685 reflections	(Δ/σ)max = 0.001
345 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.29 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	0.2687 (6)	0.7580 (2)	−0.0421 (3)	0.0725 (10)
H1A	0.1924	0.7315	−0.0733	0.087*
H1B	0.3874	0.7392	−0.0771	0.087*
C2	0.2050 (7)	0.8805 (3)	−0.0506 (3)	0.0979 (15)
H2A	0.2109	0.9119	−0.1198	0.117*
H2B	0.0827	0.8997	−0.0209	0.117*
C3	0.3143 (5)	0.9253 (3)	−0.0010 (3)	0.0780 (11)
H3A	0.2666	1.0022	−0.0039	0.094*
H3B	0.4344	0.9129	−0.0349	0.094*
C4	0.3145 (5)	0.8727 (3)	0.1047 (3)	0.0723 (10)
H4A	0.1959	0.8922	0.1397	0.087*
H4B	0.3913	0.8994	0.1353	0.087*
C5	0.3764 (5)	0.7510 (2)	0.1149 (3)	0.0643 (9)
H5A	0.4996	0.7311	0.0868	0.077*
H5B	0.3673	0.7208	0.1843	0.077*
C6	0.2685 (4)	0.7045 (2)	0.0635 (2)	0.0441 (7)
H6	0.1465	0.7190	0.0967	0.053*
C7	0.2150 (4)	0.5367 (2)	0.03513 (19)	0.0448 (7)
H7A	0.2820	0.4699	0.0126	0.054*
H7B	0.1614	0.5833	−0.0201	0.054*
C8	0.4057 (4)	0.5219 (2)	0.1526 (2)	0.0473 (7)
H8A	0.4767	0.5592	0.1763	0.057*
H8B	0.4826	0.4550	0.1349	0.057*
C9	−0.0813 (3)	0.5927 (2)	0.13368 (19)	0.0413 (6)
C10	0.2055 (4)	0.5500 (2)	0.3135 (2)	0.0445 (7)
C11	0.1351 (3)	0.4558 (2)	0.20575 (19)	0.0402 (6)
C12	0.2085 (4)	0.3346 (2)	0.2009 (2)	0.0495 (7)
C13	0.1547 (6)	0.1823 (3)	0.1599 (3)	0.0855 (12)
H13A	0.1018	0.1690	0.1074	0.103*
H13B	0.2821	0.1631	0.1425	0.103*
C14	0.1069 (9)	0.1188 (4)	0.2488 (5)	0.161 (3)
H14A	0.1588	0.1324	0.3008	0.241*
H14B	0.1487	0.0443	0.2416	0.241*
H14C	−0.0194	0.1362	0.2648	0.241*
C15	−0.0277 (3)	0.4863 (2)	0.28580 (19)	0.0413 (6)
C16	−0.1021 (4)	0.3914 (2)	0.3407 (2)	0.0512 (7)
C17	−0.3425 (6)	0.3082 (4)	0.3635 (4)	0.1058 (15)
H17A	−0.4164	0.2977	0.3196	0.127*
H17B	−0.2532	0.2420	0.3770	0.127*
C18	−0.4454 (8)	0.3377 (5)	0.4519 (5)	0.137 (2)
H18A	−0.3698	0.3440	0.4959	0.206*
H18B	−0.5079	0.2839	0.4822	0.206*
H18C	−0.5286	0.4053	0.4377	0.206*
C19	−0.2799 (4)	0.6468 (2)	0.2875 (2)	0.0514 (7)
H19A	−0.3433	0.7040	0.2422	0.062*
H19B	−0.3652	0.6114	0.3296	0.062*
C20	−0.0920 (4)	0.6070 (2)	0.4099 (2)	0.0501 (7)
H20A	−0.1691	0.5687	0.4561	0.060*
H20B	−0.0328	0.6380	0.4479	0.060*
C21	−0.1088 (4)	0.7763 (3)	0.2960 (2)	0.0604 (8)
H21	−0.0028	0.7432	0.2540	0.072*
C22	−0.0539 (5)	0.8311 (3)	0.3682 (3)	0.0768 (11)
H22A	0.0191	0.7768	0.4115	0.092*
H22B	0.0176	0.8788	0.3314	0.092*
C23	−0.2049 (7)	0.8937 (4)	0.4296 (3)	0.1020 (14)
H23A	−0.1605	0.9298	0.4707	0.122*
H23B	−0.2691	0.8453	0.4727	0.122*
C24	−0.3309 (7)	0.9774 (4)	0.3648 (4)	0.1148 (17)
H24A	−0.4356	1.0106	0.4062	0.138*
H24B	−0.2732	1.0330	0.3302	0.138*
C25	−0.3845 (6)	0.9246 (3)	0.2901 (3)	0.0932 (13)
H25A	−0.4566	0.8763	0.3248	0.112*
H25B	−0.4549	0.9794	0.2461	0.112*
C26	−0.2276 (5)	0.8638 (3)	0.2314 (3)	0.0748 (10)
H26A	−0.1598	0.9131	0.1935	0.090*
H26B	−0.2666	0.8312	0.1853	0.090*
N1	0.3357 (3)	0.58710 (17)	0.06515 (16)	0.0443 (6)
N2	0.0739 (3)	0.51436 (17)	0.11442 (15)	0.0409 (5)
N3	0.2671 (3)	0.49783 (17)	0.23314 (16)	0.0433 (6)
N4	−0.1508 (3)	0.56850 (17)	0.23033 (15)	0.0429 (6)
N5	0.0418 (3)	0.53003 (17)	0.35393 (15)	0.0425 (5)
N6	−0.1983 (3)	0.69258 (18)	0.34765 (17)	0.0499 (6)
O1	−0.1478 (2)	0.66630 (16)	0.07418 (14)	0.0522 (5)
O2	0.2829 (3)	0.59983 (16)	0.34713 (15)	0.0595 (6)
O3	0.3501 (3)	0.28529 (17)	0.2210 (2)	0.0794 (7)
O4	0.0954 (3)	0.29573 (15)	0.17002 (16)	0.0637 (6)
O5	−0.0194 (3)	0.32128 (17)	0.39407 (16)	0.0662 (6)
O6	−0.2588 (3)	0.39696 (19)	0.3181 (2)	0.0860 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.109 (3)	0.0487 (18)	0.063 (2)	−0.0210 (18)	−0.0237 (19)	−0.0020 (16)
C2	0.158 (4)	0.048 (2)	0.099 (3)	−0.026 (2)	−0.065 (3)	0.0049 (19)
C3	0.088 (3)	0.0470 (19)	0.099 (3)	−0.0224 (18)	−0.013 (2)	−0.0023 (19)
C4	0.084 (3)	0.056 (2)	0.089 (3)	−0.0222 (18)	−0.024 (2)	−0.0208 (18)
C5	0.064 (2)	0.0563 (19)	0.079 (2)	−0.0190 (16)	−0.0232 (17)	−0.0066 (16)
C6	0.0389 (15)	0.0420 (15)	0.0509 (17)	−0.0099 (12)	−0.0009 (12)	−0.0111 (13)
C7	0.0500 (17)	0.0451 (15)	0.0402 (15)	−0.0148 (13)	0.0004 (13)	−0.0104 (12)
C8	0.0401 (16)	0.0477 (16)	0.0528 (17)	−0.0084 (12)	−0.0055 (13)	−0.0086 (13)
C9	0.0422 (16)	0.0497 (16)	0.0363 (15)	−0.0150 (13)	−0.0109 (12)	−0.0065 (13)
C10	0.0467 (17)	0.0433 (15)	0.0451 (16)	−0.0065 (13)	−0.0173 (13)	−0.0064 (13)
C11	0.0420 (15)	0.0413 (15)	0.0382 (14)	−0.0101 (12)	−0.0072 (12)	−0.0063 (11)
C12	0.0519 (19)	0.0475 (17)	0.0487 (17)	−0.0129 (15)	−0.0040 (14)	−0.0076 (13)
C13	0.103 (3)	0.053 (2)	0.112 (3)	−0.021 (2)	−0.022 (3)	−0.029 (2)
C14	0.194 (6)	0.081 (3)	0.197 (7)	−0.054 (4)	0.058 (5)	−0.048 (4)
C15	0.0437 (15)	0.0446 (15)	0.0374 (14)	−0.0130 (12)	−0.0091 (12)	−0.0038 (12)
C16	0.0571 (19)	0.0546 (18)	0.0441 (17)	−0.0214 (15)	−0.0038 (14)	−0.0049 (14)
C17	0.086 (3)	0.105 (3)	0.131 (4)	−0.049 (3)	−0.006 (3)	−0.002 (3)
C18	0.128 (4)	0.132 (4)	0.130 (4)	−0.036 (4)	0.019 (4)	0.001 (4)
C19	0.0436 (16)	0.0576 (18)	0.0510 (17)	−0.0084 (14)	−0.0095 (13)	−0.0060 (14)
C20	0.0588 (18)	0.0494 (16)	0.0385 (15)	−0.0079 (14)	−0.0069 (13)	−0.0054 (13)
C21	0.058 (2)	0.064 (2)	0.0517 (18)	−0.0099 (16)	0.0007 (15)	−0.0044 (15)
C22	0.100 (3)	0.067 (2)	0.073 (2)	−0.035 (2)	−0.022 (2)	−0.0032 (19)
C23	0.140 (4)	0.099 (3)	0.075 (3)	−0.044 (3)	−0.003 (3)	−0.024 (3)
C24	0.134 (4)	0.080 (3)	0.110 (4)	−0.005 (3)	0.021 (3)	−0.031 (3)
C25	0.080 (3)	0.077 (3)	0.108 (3)	0.002 (2)	−0.014 (2)	−0.008 (2)
C26	0.084 (3)	0.062 (2)	0.071 (2)	−0.0116 (19)	−0.014 (2)	0.0030 (18)
N1	0.0435 (13)	0.0424 (13)	0.0468 (13)	−0.0104 (10)	−0.0043 (11)	−0.0081 (10)
N2	0.0430 (13)	0.0448 (12)	0.0366 (12)	−0.0119 (10)	−0.0073 (10)	−0.0068 (10)
N3	0.0392 (12)	0.0457 (13)	0.0464 (13)	−0.0097 (10)	−0.0105 (10)	−0.0068 (10)
N4	0.0380 (12)	0.0499 (13)	0.0396 (13)	−0.0070 (10)	−0.0090 (10)	−0.0055 (10)
N5	0.0493 (14)	0.0440 (12)	0.0355 (12)	−0.0103 (10)	−0.0101 (10)	−0.0064 (10)
N6	0.0527 (14)	0.0488 (14)	0.0458 (13)	−0.0085 (11)	−0.0077 (11)	−0.0061 (11)
O1	0.0509 (12)	0.0597 (12)	0.0440 (11)	−0.0082 (10)	−0.0164 (9)	−0.0018 (10)
O2	0.0541 (13)	0.0670 (13)	0.0675 (14)	−0.0150 (10)	−0.0230 (11)	−0.0208 (11)
O3	0.0584 (15)	0.0511 (13)	0.125 (2)	−0.0008 (11)	−0.0252 (14)	−0.0112 (13)
O4	0.0746 (15)	0.0452 (12)	0.0788 (15)	−0.0124 (11)	−0.0240 (12)	−0.0183 (10)
O5	0.0860 (16)	0.0578 (13)	0.0567 (13)	−0.0258 (12)	−0.0187 (12)	0.0070 (11)
O6	0.0630 (16)	0.0772 (16)	0.120 (2)	−0.0393 (13)	−0.0197 (14)	0.0182 (15)

Geometric parameters (Å, º)

C1—C6	1.504 (4)	C14—H14A	0.96
C1—C2	1.535 (5)	C14—H14B	0.96
C1—H1A	0.97	C14—H14C	0.96
C1—H1B	0.97	C15—N4	1.446 (3)
C2—C3	1.490 (5)	C15—N5	1.449 (3)
C2—H2A	0.97	C15—C16	1.534 (4)
C2—H2B	0.97	C16—O5	1.188 (3)
C3—C4	1.502 (5)	C16—O6	1.315 (4)
C3—H3A	0.97	C17—C18	1.409 (7)
C3—H3B	0.97	C17—O6	1.476 (5)
C4—C5	1.522 (4)	C17—H17A	0.97
C4—H4A	0.97	C17—H17B	0.97
C4—H4B	0.97	C18—H18A	0.96
C5—C6	1.512 (4)	C18—H18B	0.96
C5—H5A	0.97	C18—H18C	0.96
C5—H5B	0.97	C19—N6	1.442 (4)
C6—N1	1.482 (3)	C19—N4	1.479 (3)
C6—H6	0.98	C19—H19A	0.97
C7—N1	1.456 (3)	C19—H19B	0.97
C7—N2	1.473 (3)	C20—N6	1.448 (3)
C7—H7A	0.97	C20—N5	1.475 (3)
C7—H7B	0.97	C20—H20A	0.97
C8—N1	1.452 (3)	C20—H20B	0.97
C8—N3	1.476 (3)	C21—N6	1.470 (4)
C8—H8A	0.97	C21—C22	1.524 (5)
C8—H8B	0.97	C21—C26	1.527 (4)
C9—O1	1.212 (3)	C21—H21	0.98
C9—N4	1.372 (3)	C22—C23	1.487 (6)
C9—N2	1.393 (3)	C22—H22A	0.97
C10—O2	1.209 (3)	C22—H22B	0.97
C10—N3	1.370 (4)	C23—C24	1.538 (6)
C10—N5	1.392 (4)	C23—H23A	0.97
C11—N3	1.443 (3)	C23—H23B	0.97
C11—N2	1.445 (3)	C24—C25	1.528 (7)
C11—C12	1.546 (4)	C24—H24A	0.97
C11—C15	1.565 (4)	C24—H24B	0.97
C12—O3	1.186 (3)	C25—C26	1.484 (5)
C12—O4	1.311 (3)	C25—H25A	0.97
C13—C14	1.407 (7)	C25—H25B	0.97
C13—O4	1.458 (4)	C26—H26A	0.97
C13—H13A	0.97	C26—H26B	0.97
C13—H13B	0.97
C6—C1—C2	112.0 (3)	O5—C16—C15	121.3 (3)
C6—C1—H1A	109.2	O6—C16—C15	112.1 (3)
C2—C1—H1A	109.2	C18—C17—O6	106.5 (4)
C6—C1—H1B	109.2	C18—C17—H17A	110.4
C2—C1—H1B	109.2	O6—C17—H17A	110.4
H1A—C1—H1B	107.9	C18—C17—H17B	110.4
C3—C2—C1	111.5 (3)	O6—C17—H17B	110.4
C3—C2—H2A	109.3	H17A—C17—H17B	108.6
C1—C2—H2A	109.3	C17—C18—H18A	109.5
C3—C2—H2B	109.3	C17—C18—H18B	109.5
C1—C2—H2B	109.3	H18A—C18—H18B	109.5
H2A—C2—H2B	108.0	C17—C18—H18C	109.5
C2—C3—C4	109.8 (3)	H18A—C18—H18C	109.5
C2—C3—H3A	109.7	H18B—C18—H18C	109.5
C4—C3—H3A	109.7	N6—C19—N4	112.9 (2)
C2—C3—H3B	109.7	N6—C19—H19A	109.0
C4—C3—H3B	109.7	N4—C19—H19A	109.0
H3A—C3—H3B	108.2	N6—C19—H19B	109.0
C3—C4—C5	112.5 (3)	N4—C19—H19B	109.0
C3—C4—H4A	109.1	H19A—C19—H19B	107.8
C5—C4—H4A	109.1	N6—C20—N5	113.2 (2)
C3—C4—H4B	109.1	N6—C20—H20A	108.9
C5—C4—H4B	109.1	N5—C20—H20A	108.9
H4A—C4—H4B	107.8	N6—C20—H20B	108.9
C6—C5—C4	111.9 (3)	N5—C20—H20B	108.9
C6—C5—H5A	109.2	H20A—C20—H20B	107.7
C4—C5—H5A	109.2	N6—C21—C22	111.6 (3)
C6—C5—H5B	109.2	N6—C21—C26	111.8 (3)
C4—C5—H5B	109.2	C22—C21—C26	107.1 (3)
H5A—C5—H5B	107.9	N6—C21—H21	108.7
N1—C6—C1	108.6 (2)	C22—C21—H21	108.7
N1—C6—C5	112.9 (2)	C26—C21—H21	108.7
C1—C6—C5	109.6 (2)	C23—C22—C21	114.0 (3)
N1—C6—H6	108.5	C23—C22—H22A	108.8
C1—C6—H6	108.5	C21—C22—H22A	108.8
C5—C6—H6	108.5	C23—C22—H22B	108.8
N1—C7—N2	113.6 (2)	C21—C22—H22B	108.8
N1—C7—H7A	108.9	H22A—C22—H22B	107.7
N2—C7—H7A	108.9	C22—C23—C24	111.1 (3)
N1—C7—H7B	108.9	C22—C23—H23A	109.4
N2—C7—H7B	108.9	C24—C23—H23A	109.4
H7A—C7—H7B	107.7	C22—C23—H23B	109.4
N1—C8—N3	113.3 (2)	C24—C23—H23B	109.4
N1—C8—H8A	108.9	H23A—C23—H23B	108.0
N3—C8—H8A	108.9	C25—C24—C23	110.5 (3)
N1—C8—H8B	108.9	C25—C24—H24A	109.5
N3—C8—H8B	108.9	C23—C24—H24A	109.5
H8A—C8—H8B	107.7	C25—C24—H24B	109.5
O1—C9—N4	125.9 (2)	C23—C24—H24B	109.5
O1—C9—N2	125.9 (2)	H24A—C24—H24B	108.1
N4—C9—N2	108.1 (2)	C26—C25—C24	111.5 (4)
O2—C10—N3	126.4 (3)	C26—C25—H25A	109.3
O2—C10—N5	125.5 (3)	C24—C25—H25A	109.3
N3—C10—N5	108.0 (2)	C26—C25—H25B	109.3
N3—C11—N2	111.9 (2)	C24—C25—H25B	109.3
N3—C11—C12	109.7 (2)	H25A—C25—H25B	108.0
N2—C11—C12	111.9 (2)	C25—C26—C21	112.4 (3)
N3—C11—C15	103.3 (2)	C25—C26—H26A	109.1
N2—C11—C15	103.9 (2)	C21—C26—H26A	109.1
C12—C11—C15	115.9 (2)	C25—C26—H26B	109.1
O3—C12—O4	125.5 (3)	C21—C26—H26B	109.1
O3—C12—C11	123.5 (3)	H26A—C26—H26B	107.9
O4—C12—C11	111.0 (2)	C8—N1—C7	109.1 (2)
C14—C13—O4	110.3 (4)	C8—N1—C6	118.8 (2)
C14—C13—H13A	109.6	C7—N1—C6	114.0 (2)
O4—C13—H13A	109.6	C9—N2—C11	110.3 (2)
C14—C13—H13B	109.6	C9—N2—C7	121.3 (2)
O4—C13—H13B	109.6	C11—N2—C7	114.6 (2)
H13A—C13—H13B	108.1	C10—N3—C11	112.5 (2)
C13—C14—H14A	109.5	C10—N3—C8	125.6 (2)
C13—C14—H14B	109.5	C11—N3—C8	115.6 (2)
H14A—C14—H14B	109.5	C9—N4—C15	112.3 (2)
C13—C14—H14C	109.5	C9—N4—C19	124.1 (2)
H14A—C14—H14C	109.5	C15—N4—C19	115.9 (2)
H14B—C14—H14C	109.5	C10—N5—C15	111.0 (2)
N4—C15—N5	111.8 (2)	C10—N5—C20	121.0 (2)
N4—C15—C16	114.1 (2)	C15—N5—C20	114.5 (2)
N5—C15—C16	109.9 (2)	C19—N6—C20	109.2 (2)
N4—C15—C11	102.81 (19)	C19—N6—C21	116.3 (2)
N5—C15—C11	103.3 (2)	C20—N6—C21	114.4 (2)
C16—C15—C11	114.3 (2)	C12—O4—C13	115.2 (3)
O5—C16—O6	126.5 (3)	C16—O6—C17	117.5 (3)
C6—C1—C2—C3	57.1 (5)	C15—C11—N2—C7	155.8 (2)
C1—C2—C3—C4	−55.8 (5)	N1—C7—N2—C9	84.6 (3)
C2—C3—C4—C5	55.6 (4)	N1—C7—N2—C11	−51.8 (3)
C3—C4—C5—C6	−55.5 (4)	O2—C10—N3—C11	−173.7 (3)
C2—C1—C6—N1	−178.6 (3)	N5—C10—N3—C11	9.9 (3)
C2—C1—C6—C5	−54.8 (4)	O2—C10—N3—C8	−22.9 (4)
C4—C5—C6—N1	175.2 (3)	N5—C10—N3—C8	160.7 (2)
C4—C5—C6—C1	54.0 (4)	N2—C11—N3—C10	109.3 (2)
N3—C11—C12—O3	2.8 (4)	C12—C11—N3—C10	−125.9 (2)
N2—C11—C12—O3	127.5 (3)	C15—C11—N3—C10	−1.8 (3)
C15—C11—C12—O3	−113.6 (3)	N2—C11—N3—C8	−44.6 (3)
N3—C11—C12—O4	−176.0 (2)	C12—C11—N3—C8	80.2 (3)
N2—C11—C12—O4	−51.2 (3)	C15—C11—N3—C8	−155.7 (2)
C15—C11—C12—O4	67.6 (3)	N1—C8—N3—C10	−99.7 (3)
N3—C11—C15—N4	109.9 (2)	N1—C8—N3—C11	50.3 (3)
N2—C11—C15—N4	−7.0 (2)	O1—C9—N4—C15	−171.2 (2)
C12—C11—C15—N4	−130.2 (2)	N2—C9—N4—C15	12.1 (3)
N3—C11—C15—N5	−6.5 (2)	O1—C9—N4—C19	−23.2 (4)
N2—C11—C15—N5	−123.4 (2)	N2—C9—N4—C19	160.2 (2)
C12—C11—C15—N5	113.4 (2)	N5—C15—N4—C9	107.4 (2)
N3—C11—C15—C16	−125.9 (2)	C16—C15—N4—C9	−127.1 (2)
N2—C11—C15—C16	117.2 (2)	C11—C15—N4—C9	−2.8 (3)
C12—C11—C15—C16	−6.0 (3)	N5—C15—N4—C19	−43.5 (3)
N4—C15—C16—O5	−175.3 (3)	C16—C15—N4—C19	82.0 (3)
N5—C15—C16—O5	−48.8 (4)	C11—C15—N4—C19	−153.7 (2)
C11—C15—C16—O5	66.8 (3)	N6—C19—N4—C9	−97.0 (3)
N4—C15—C16—O6	7.0 (3)	N6—C19—N4—C15	50.1 (3)
N5—C15—C16—O6	133.5 (3)	O2—C10—N5—C15	169.0 (2)
C11—C15—C16—O6	−110.9 (3)	N3—C10—N5—C15	−14.6 (3)
N6—C21—C22—C23	−65.8 (4)	O2—C10—N5—C20	30.7 (4)
C26—C21—C22—C23	56.9 (4)	N3—C10—N5—C20	−152.9 (2)
C21—C22—C23—C24	−55.5 (5)	N4—C15—N5—C10	−97.0 (2)
C22—C23—C24—C25	51.8 (5)	C16—C15—N5—C10	135.3 (2)
C23—C24—C25—C26	−53.8 (5)	C11—C15—N5—C10	12.9 (3)
C24—C25—C26—C21	58.5 (5)	N4—C15—N5—C20	44.3 (3)
N6—C21—C26—C25	64.8 (4)	C16—C15—N5—C20	−83.5 (3)
C22—C21—C26—C25	−57.8 (4)	C11—C15—N5—C20	154.1 (2)
N3—C8—N1—C7	−53.0 (3)	N6—C20—N5—C10	84.7 (3)
N3—C8—N1—C6	79.9 (3)	N6—C20—N5—C15	−52.4 (3)
N2—C7—N1—C8	54.1 (3)	N4—C19—N6—C20	−54.2 (3)
N2—C7—N1—C6	−81.2 (3)	N4—C19—N6—C21	77.2 (3)
C1—C6—N1—C8	158.8 (3)	N5—C20—N6—C19	55.9 (3)
C5—C6—N1—C8	37.0 (3)	N5—C20—N6—C21	−76.5 (3)
C1—C6—N1—C7	−70.4 (3)	C22—C21—N6—C19	170.8 (3)
C5—C6—N1—C7	167.8 (2)	C26—C21—N6—C19	50.9 (3)
O1—C9—N2—C11	166.3 (2)	C22—C21—N6—C20	−60.3 (3)
N4—C9—N2—C11	−17.0 (3)	C26—C21—N6—C20	179.8 (2)
O1—C9—N2—C7	28.2 (4)	O3—C12—O4—C13	−0.5 (5)
N4—C9—N2—C7	−155.1 (2)	C11—C12—O4—C13	178.2 (3)
N3—C11—N2—C9	−96.1 (2)	C14—C13—O4—C12	89.7 (5)
C12—C11—N2—C9	140.4 (2)	O5—C16—O6—C17	0.4 (5)
C15—C11—N2—C9	14.7 (3)	C15—C16—O6—C17	178.0 (3)
N3—C11—N2—C7	45.1 (3)	C18—C17—O6—C16	91.1 (5)
C12—C11—N2—C7	−78.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20B···O5^i	0.97	2.49	3.381 (4)	152
C17—H17A···O3^ii	0.97	2.55	3.513 (6)	171

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