Synthesis and crystal structure of 2-amino-4-(3-isobutyl-1-phenyl-1H-pyrazol-4-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetra­hydro-4H-chromene-3-carbo­nitrile

Salama, H.T.; Abu-Zaied, M.A.; Azzam, R.A.; Hebishy, A.M.S.; Elgemeie, G.H.; Jones, P.G.

doi:10.1107/S2056989026006973

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ISSN: 2056-9890

Volume 82| Part 8| August 2026| Pages 928-932

https://doi.org/10.1107/S2056989026006973

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Synthesis and crystal structure of 2-amino-4-(3-isobutyl-1-phenyl-1H-pyrazol-4-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

Hagar T. Salama,^a Mamdouh A. Abu-Zaied,^b Rasha A. Azzam,^a Ali M. S. Hebishy,^a Galal H. Elgemeie ^a and Peter G. Jones ^c ^*

^aChemistry Department, Faculty of Science, Capital University, Helwan, Egypt, ^bGreen Chemistry Department, National Research Centre, Dokki, Giza, Egypt, and ^cInstitut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany
^*Correspondence e-mail: [email protected]

Edited by C. Schulzke, Universität Greifswald, Germany (Received 10 June 2026; accepted 3 July 2026; online 16 July 2026)

The title compound, C₂₅H₂₈N₄O₂, crystallizes in space group P1 with Z = 4. The two independent molecules are related by the approximate translation (x + 1, y + 1, z), but differ in the orientation of the phenyl substituent. Crystals are non-merohedrally twinned by a 180° rotation about c*. In the modified chromene ring systems, the two formal double bonds are the shortest C—C bonds. The oxo ring displays a flattened boat conformation, whereas the other ring is approximately a flattened envelope, with the CMe₂ C atom out of the plane. The molecules are connected by classical N—H⋯N_pyrazole hydrogen bonds to form a ribbon of alternating independent molecules parallel to [110]. The ribbons are joined by weak C_pyrazole—H⋯N_nitrile hydrogen bonds to form a layer structure parallel to the ab plane in the region z ≃ 3/4.

Keywords: crystal structure; chromene; pyrazole; hydrogen bonds; twinning.

CCDC reference: 2570429

1. Chemical context

Chromene derivatives represent an important class of oxygen-containing heterocyclic compounds that continue to attract significant attention in medicinal and synthetic organic chemistry because of their wide range of biological and pharmacological activities, which include antimicrobial, antioxidant, anti-inflammatory, antiviral, antidiabetic and anticancer properties (Chaudary et al., 2022 ; Kativar et al., 2022 ; Patel et al., 2025 ). Moreover, the chromene scaffold is considered a privileged structural motif that is frequently encountered in natural products and bioactive synthetic molecules, because of its importance in drug discovery and medicinal chemistry research (Raj et al., 2013 ; Welsch et al., 2010 ).

Among these systems, 2-amino-4H-chromene derivatives have received particular interest because of their facile synthetic accessibility and biological potential. They are widely used as key building blocks for the synthesis of more complex heterocyclic systems. Thus, combining the chromene framework with other biologically active heterocycles, such as pyrazole rings, has been shown to generate hybrid structures with enhanced pharmacological properties related to synergistic electronic and structural effects (Santos et al., 2017 ; Hebishy et al., 2022 ).

From a synthetic point of view, multicomponent reactions are among the most efficient and widely used strategies for constructing chromene derivatives. These methods are attractive because they are operationally simple, environmentally friendly and provide high atom economy with good yields, making them suitable for the rapid generation of diverse chromene libraries (Kidwai et al., 2005 ; Abdallah et al., 2022 ; Abdallah et al., 2023a ; Abdallah et al., 2023b ).

In this context, our laboratory (the Elgemeie group) has recently contributed to the field of heterocyclic chemistry, particularly in the development of new synthetic methodologies and biologically active nitrogen- and oxygen-containing heterocyclic systems, including pyrazole-based frameworks (Elboshi et al., 2024 ).

The reaction (Fig. 1) between the pyrazole methylenemalononitrile derivative 1 and dimedone 2 was carried out in refluxing ethanol in the presence of a few drops of triethylamine with continuous stirring. After 2 h, the desired chromene derivative 5 was isolated. The synthesis probably proceeds through initial formation of the intermediate Michael addition product 3, followed by intramolecular cyclization to 4, finally leading to the product 5. The structure of 5 was deduced on the basis of IR and ¹H NMR spectroscopic analyses. The IR spectrum displayed characteristic absorption bands at 3360 cm⁻¹ corresponding to the amino group, 2215 cm⁻¹ attributed to the nitrile functionality and 1741 cm⁻¹ assigned to the carbonyl group. Additional confirmation was obtained from the ¹H NMR spectrum. A characteristic singlet appeared at δ 4.27 ppm and was assigned to the methine proton of the chromene ring system. Moreover, the disappearance of the vinylic proton signal, present in the starting material 1, indicated successful cyclization and formation of the chromene framework. The spectrum also showed the appearance of a new signal at δ 6.94 ppm corresponding to the amino group (NH₂), providing further evidence for the formation of the target compound. Unambiguous confirmation of the nature of 5 was provided by the X-ray structure determination, presented here.

Figure 1
The synthesis of compound 5 (TEA = triethylamine).

2. Structural commentary

The structure of compound 5 in the crystal is shown in Fig. 2; there are two molecules in the asymmetric unit, related approximately by the translation (x + 1, y + 1, z), and differing mainly in the orientation of phenyl ring C21–26. Atom names of the second molecule are distinguished by primes (′). Both independent molecules have the configuration S at C4, the only stereogenic C atom (although the overall constitution is of course a racemate). Selected molecular dimensions are given in Table 1. A least-squares fit of both molecules, considering all non-H atoms except C22–26 (Fig. 3; cf. torsion angles in Table 1) gives an r.m.s. deviation (rmsd) of 0.11 Å.

Table 1
Selected geometric parameters (Å, °)

C2—C3	1.3623 (12)	C2′—C3′	1.3629 (12)
C4A—C8A	1.3404 (12)	C4A′—C8A′	1.3446 (12)
N11—C15	1.3644 (12)	N11′—C15′	1.3627 (12)
N11—N12	1.3644 (11)	N11′—N12′	1.3631 (11)
N12—C13	1.3368 (11)	N12′—C13′	1.3371 (11)
C13—C14	1.4176 (12)	C13′—C14′	1.4183 (12)
C14—C15	1.3800 (12)	C14′—C15′	1.3809 (12)

C4A—C4—C3	108.28 (7)	C4A′—C4′—C3′	108.14 (7)
C6—C7—C8	108.76 (7)	C6′—C7′—C8′	108.67 (7)
C4A—C8A—C8	126.01 (8)	C4A′—C8A′—C8′	125.76 (8)

C3—C4—C14—C15	−72.98 (11)	C3′—C4′—C14′—C15′	−68.38 (11)
C3—C4—C14—C13	103.58 (10)	C3′—C4′—C14′—C13′	109.27 (10)
N12—N11—C21—C22	166.67 (8)	N12′—N11′—C21′—C22′	−164.36 (9)
N12—N11—C21—C26	−14.27 (13)	N12′—N11′—C21′—C26′	15.71 (13)

Figure 2
The asymmetric unit of compound 5 in the crystal. Displacement ellipsoids correspond to 50% probability levels. The dashed line indicates a classical hydrogen bond.

Figure 3
A least-squares fit of the two independent molecules of 5, showing the different orientations of the ring at C21. The second molecule is shown with green dashed bonds. Fitted atoms of the first molecule (magenta bonds) are labelled.

In the (substantially modified) chromene ring systems, the formal double bonds C2=C3 and C4A=C8A are by far the shortest C—C bonds. The sp³ hybridization of C4 means that the ring angle at this atom is substantially more acute than other angles of the oxo ring. This ring displays a flattened boat conformation, with O1 lying 0.082 (1) and C4 0.156 (1) Å to the same side of the plane of the other four atoms (rmsd 0.004 Å); in the second molecule, the corresponding values are 0.090 (1) and 0.193 (1) Å, rmsd 0.003 Å. The second ring is approximately a flattened envelope, with C7 lying 0.588 (1) Å out of the plane of the other five atoms (rmsd 0.061 Å); in the second molecule, C7′ lies 0.596 (1) Å out of plane, rmsd 0.057 Å. The bond angles of this ring, with formal sp³ hybridization at C6, C7 and C8, but sp² at C4A, C5 and C8A, vary considerably, with the widest at C8A and the narrowest at C7 [126.01 (8) and 108.76 (7)°, respectively]. Other molecular dimensions (e.g. of the pyrazole rings) may be regarded as unexceptional.

The interplanar angles between the pyrazole and phenyl rings are 14.66 (6)° for molecule 1 (rmsd of individual rings: 0.004 and 0.005 Å) and 14.67 (7)° (0.003 and 0.007 Å) for molecule 2. However, these figures mask the fact that the mutual rotation is in opposite senses for the two molecules (see above and Fig. 3), so that the relevant torsion angles have opposite signs. The torsion angles about the bond C4—C14 (and C4′—C14′), defining the relative orientation of the oxo and pyrazole rings, differ by ca 4–6°.

3. Supramolecular features

Hydrogen bonds are listed in Table 2. The molecules of 5 are connected by classical hydrogen bonds N1′—H01′⋯N12 and N1—H01⋯N12′ (x + 1, y + 1, z) to form a ribbon of alternating independent molecules parallel to [110]. Three such ribbons are shown, running horizontally, in Fig. 4. Adjacent ribbons are joined by weak hydrogen bonds from the pyrazole rings to the nitrile N atoms, namely C15—H15⋯N2′ (x, y + 1, z) and C15′—H15′⋯N2 (x − 1, y, z) to form a layer structure parallel to the ab plane in the region z ≃ 3/4 (a further such layer, but inverted, occupies the region z ≃ 1/4). Layers are connected in the third dimension by C_methyl—H⋯O=C contacts (not shown in Fig. 4). It is noteworthy that the potential hydrogen-bond donors H02 and H02′ form neither classical nor weak hydrogen bonds, but instead are directed towards phenyl rings, with N1—H02⋯Cg(C21–26) = 2.83 and N1′—H02′⋯Cg(C21′–26′) = 2.98 Å (operator: x + 1, y, z in both cases). The H⋯C distances however vary considerably, the shortest for each H atom being H02⋯C24 = 2.74 (2) and H02′⋯C25′ = 2.53 (2) Å. These contacts can be recognized between adjacent ribbons in Fig. 4, but are not drawn explicitly.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1′—H01′⋯N12	0.878 (17)	2.115 (17)	2.9895 (11)	173.5 (14)
N1—H01⋯N12′ⁱ	0.868 (16)	2.145 (16)	3.0071 (11)	172.0 (15)
C15—H15⋯N2′ⁱⁱ	0.95	2.41	3.3622 (13)	176
C15′—H15′⋯N2ⁱⁱⁱ	0.95	2.43	3.3816 (13)	180
C11—H11A⋯O2′^iv	0.98	2.47	3.3965 (12)	157
C11′—H11D⋯O2^iv	0.98	2.59	3.5046 (13)	155
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

Figure 4
Packing diagram of compound 5, viewed parallel to the c axis in the region z ≃ 3/4. Molecules are connected by classical hydrogen bonds (thick dashed lines) to form ribbons parallel to [110] (horizontal; three such ribbons are shown). Ribbons are connected by weak hydrogen bonds C—H⋯N≡C (thin dashed lines) and perhaps also by C—H⋯π contacts (not drawn explicitly; see text). The alternating orientations of the rings C21–26 and C21′–26′ are clearly recognizable (e.g. at the top of the diagram)..

4. Database survey

Searches were conducted using the Cambridge Structural Database (CSD, Version 6.01, update November 2025; Groom et al., 2016 ) and the ConQuest routine (Version 2025.3.1; Bruno et al., 2002 ).

A search for the 5,6,7,8-tetrahydro-4H-chromene skeleton, allowing any substitution but omitting further annelated rings, gave 387 hits. Restricting the search to 2-amino-3-carbonitrile derivatives with a C and an H substituent at C4 still gave 148 hits, showing that this is a much-studied group of compounds. Finally, restricting the non-H substituent at C4 to a non-annelated five-membered ring gave only 6 hits; these involved 1,2-thiazole or 1,2-oxazole (refcodes PUFPUF and PUFQAM; Potkin et al., 2024 ), thiophene (QEFVUW and UGUPUL; Zamisa et al., 2022 ; Nyapola et al., 2024 ) or furan (VAMRIO and XUYCUQ; Kalantari et al., 2021 ; Song et al., 2010 ) derivatives.

Alternatively, restricting the substitution at C7 to dimethyl, while still ruling out further annelation, gave just one hit, also a 2-amino-3-carbonitrile derivative, namely, 2-amino-4-(4-methoxyphenyl)-6,6-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-1-benzopyran-3-carbonitrile (OCEWUS; Djedouani & Bourzami, 2021 ).

5. Synthesis and crystallization

The synthesis, including a proposed mechanism, is shown in Fig. 1. To a solution of 2-[(3-isobutyl-1-phenyl-1H-pyrazol-4-yl)methylidene]malononitrile, 1 (1 mmol), in ethanol (20 ml) was added 5,5-dimethylcyclohexane-1,3-dione, 2 (1 mmol). Subsequently, a few drops of triethylamine were added and the reaction mixture was heated under reflux for 2 h. The progress of the reaction was monitored by thin-layer chromatography (TLC). After completion of the reaction, the precipitate was collected by hot filtration, washed with ethanol, dried and recrystallized from ethanol to afford colourless crystals of the desired product 5 (yield: 0.395 g, 95%; m.p. 482–484 K). IR (cm⁻¹) : ν 3360 (NH₂), 2949 (CH₃), 2215 (C≡N), 1741 (C=O); ¹H NMR (400 MHz, DMSO-d₆): δ ppm 0.99–1.08 (m, 12H, 4 × CH₃), 2.07–2.14 (m, 1H, CH), 2.18 (d, J = 14 Hz, 2H, chromene-CH₂), 2.54–2.59 (m, 2H, chromene-CH₂), 4.27 (s, 1H, chromene-CH), 6.94 (s, D₂O-exchangeable, 2H, NH₂), 7.22 (t, J = 7.6 Hz, 1H, Ar-H), 7.43 (t, J = 8.4 Hz, 2H, Ar-H), 7.76 (d, J = 8.0 Hz, 2H, Ar-H), 8.15 (s, 1H, pyrazole-H). Analysis calculated (%) for C₂₅H₂₈N₄O₂: C 72.09, H 6.78, N 13.45; found: C 72.10, H 6.80; N 13.47.

6. Refinement

Details of data collection and structure refinement are summarized in Table 3.

Table 3
Experimental details

Crystal data
Chemical formula	C₂₅H₂₈N₄O₂
M_r	416.51
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	10.6988 (4), 12.0191 (4), 18.3578 (6)
α, β, γ (°)	83.864 (3), 80.248 (3), 69.426 (3)
V (Å³)	2175.26 (14)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.18 × 0.12 × 0.05

Data collection
Diffractometer	Bruker XtaLAB Synergy
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2026)
T_min, T_max	0.860, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	24964, 24964, 20260
R_int	See Refinement section
θ values (°)	θ_max = 38.6, θ_min = 2.1
(sin θ/λ)_max (Å⁻¹)	0.877

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.133, 1.04
No. of reflections	24964
No. of parameters	584
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.29
Computer programs: CrysAlis PRO (Rigaku OD, 2026), SHELXT (Sheldrick, 2015a ), SHELXL2019 (Sheldrick, 2015b ), XP (Bruker, 1998 ) and publCIF (Westrip, 2010 ).

The structure was refined as a two-component non-merohedral twin (involving 180° rotation about c*) using the ‘HKLF 5' method. The relative contribution of the smaller twin component refined to 0.4461 (6). The dataset comprises all overlapped and non-overlapped reflections from both components, so that the number of reflections given in Table 3 should be interpreted with caution. R_int is meaningless because equivalents are merged during the data reduction of twins with CrysAlis PRO (Rigaku OD, 2026 ).

Atom names of the second independent molecule are distinguished by primes (′). H atoms of the NH₂ groups were refined freely. The methyl groups were refined as idealized rigid groups, with C—H 0.98 Å and H—C—H 109.5°, allowed to rotate but not tip (AFIX 137). Other H atoms were included using a riding model starting from calculated positions, with C—H = 1.00, 0.99 and 0.95 Å for methine, methylene and aromatic H atoms, respectively. The U_eq(H) values were fixed at 1.5U_eq of the parent C atoms for the methyl groups and at 1.2U_eq for the other H atoms. Three badly-fitting reflections with Δ/σ > 10 were omitted from the refinement.

CheckCIF suggests missing translational symmetry between the two independent molecules (translation x + 1, y + 1, z), but this is only approximate (see, for example, the differing orientations of the phenyl groups for the two molecules, as discussed above).

Supporting information

CCDC reference: 2570429

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989026006973/yz2082sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026006973/yz2082Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026006973/yz2082Isup3.cml

checkCIF report

Computing details top

2-Amino-4-(3-isobutyl-1-phenyl-1H-pyrazol-4-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile top

Crystal data top

C₂₅H₂₈N₄O₂	Z = 4
M_r = 416.51	F(000) = 888
Triclinic, P1	D_x = 1.272 Mg m⁻³
a = 10.6988 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.0191 (4) Å	Cell parameters from 47190 reflections
c = 18.3578 (6) Å	θ = 2.2–39.6°
α = 83.864 (3)°	µ = 0.08 mm⁻¹
β = 80.248 (3)°	T = 100 K
γ = 69.426 (3)°	Block, colourless
V = 2175.26 (14) Å³	0.18 × 0.12 × 0.05 mm

Data collection top

Bruker XtaLAB Synergy diffractometer	24964 measured reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source	24964 independent reflections
Mirror monochromator	20260 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	θ_max = 38.6°, θ_min = 2.1°
ω scans	h = −18→18
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2026)	k = −21→21
T_min = 0.860, T_max = 1.000	l = −32→32

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.133	w = 1/[σ²(F_o²) + (0.0823P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
24964 reflections	Δρ_max = 0.50 e Å⁻³
584 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	1.03615 (7)	0.87672 (6)	0.73010 (4)	0.01311 (11)
C2	1.12004 (9)	0.77845 (7)	0.69375 (5)	0.01168 (13)
C3	1.09881 (8)	0.67220 (7)	0.70413 (5)	0.01130 (13)
C4	0.97828 (8)	0.65456 (7)	0.75463 (5)	0.01088 (13)
H4	1.012593	0.584062	0.789162	0.013*
C4A	0.91003 (9)	0.76258 (7)	0.80014 (5)	0.01118 (13)
C5	0.81237 (9)	0.75435 (8)	0.86584 (5)	0.01327 (14)
C6	0.72387 (9)	0.86867 (8)	0.90112 (5)	0.01458 (15)
H6A	0.685693	0.849908	0.951979	0.018*
H6B	0.647854	0.908341	0.872649	0.018*
C7	0.80005 (9)	0.95482 (8)	0.90446 (5)	0.01311 (14)
C8	0.86883 (9)	0.97571 (8)	0.82595 (5)	0.01387 (14)
H8A	0.800163	1.031625	0.797127	0.017*
H8B	0.936126	1.013455	0.829478	0.017*
C8A	0.93736 (9)	0.86397 (8)	0.78557 (5)	0.01147 (13)
C9	1.18878 (9)	0.57506 (8)	0.66364 (5)	0.01410 (14)
C10	0.70049 (10)	1.07310 (9)	0.93309 (6)	0.01883 (17)
H10A	0.656800	1.059625	0.982990	0.028*
H10B	0.631947	1.107160	0.900028	0.028*
H10C	0.748914	1.128338	0.934599	0.028*
C11	0.90628 (10)	0.90137 (9)	0.95686 (5)	0.01641 (16)
H11A	0.862044	0.885605	1.006165	0.025*
H11B	0.952675	0.957596	0.960027	0.025*
H11C	0.971956	0.826772	0.937852	0.025*
N11	0.72968 (8)	0.65100 (7)	0.63907 (4)	0.01300 (13)
N12	0.77313 (8)	0.53324 (7)	0.66106 (4)	0.01358 (13)
C13	0.86526 (9)	0.52040 (8)	0.70515 (5)	0.01247 (14)
C14	0.88152 (9)	0.63071 (7)	0.71208 (5)	0.01147 (13)
C15	0.79426 (9)	0.71150 (8)	0.66850 (5)	0.01307 (14)
H15	0.781511	0.793932	0.660488	0.016*
C16	0.93578 (9)	0.40083 (8)	0.73944 (5)	0.01562 (15)
H16A	1.033842	0.386946	0.731277	0.019*
H16B	0.921007	0.339576	0.713312	0.019*
C17	0.89145 (10)	0.38313 (9)	0.82300 (6)	0.01776 (17)
H17	0.912874	0.441064	0.849656	0.021*
C18	0.74040 (11)	0.40549 (11)	0.84093 (7)	0.0260 (2)
H18A	0.690560	0.486101	0.822925	0.039*
H18B	0.715587	0.397308	0.894617	0.039*
H18C	0.717992	0.347451	0.816784	0.039*
C19	0.97173 (13)	0.25766 (10)	0.84956 (8)	0.0284 (2)
H19A	0.952334	0.199518	0.823822	0.043*
H19B	0.946136	0.247012	0.902999	0.043*
H19C	1.068321	0.245788	0.838950	0.043*
C21	0.63208 (9)	0.69587 (8)	0.58987 (5)	0.01323 (14)
C22	0.56792 (10)	0.81835 (8)	0.57979 (5)	0.01687 (16)
H22	0.589748	0.872145	0.605423	0.020*
C23	0.47161 (10)	0.86106 (9)	0.53182 (5)	0.01902 (17)
H23	0.427163	0.944361	0.525138	0.023*
C24	0.43990 (10)	0.78300 (9)	0.49364 (5)	0.01865 (17)
H24	0.373450	0.812711	0.461390	0.022*
C25	0.50581 (11)	0.66156 (10)	0.50290 (6)	0.02197 (19)
H25	0.485252	0.608047	0.476339	0.026*
C26	0.60208 (11)	0.61742 (9)	0.55093 (6)	0.02040 (18)
H26	0.647045	0.534104	0.557058	0.024*
O2	0.80446 (8)	0.65736 (7)	0.88973 (4)	0.01929 (14)
N1	1.22003 (9)	0.80417 (8)	0.64810 (5)	0.01663 (14)
H01	1.2362 (15)	0.8692 (14)	0.6514 (9)	0.021 (4)*
H02	1.2847 (17)	0.7476 (16)	0.6228 (10)	0.035 (5)*
N2	1.25994 (10)	0.49270 (8)	0.63172 (5)	0.02255 (18)
O1'	0.51350 (7)	0.38781 (6)	0.73024 (4)	0.01354 (11)
C2'	0.60315 (9)	0.29023 (8)	0.69527 (5)	0.01174 (13)
C3'	0.59363 (9)	0.17973 (7)	0.71029 (5)	0.01188 (13)
C4'	0.47740 (9)	0.15715 (7)	0.76234 (5)	0.01175 (13)
H4'	0.515849	0.088341	0.797219	0.014*
C4A'	0.40446 (9)	0.26552 (8)	0.80681 (5)	0.01190 (13)
C5'	0.31341 (9)	0.25433 (8)	0.87492 (5)	0.01413 (14)
C6'	0.22061 (9)	0.36745 (8)	0.91023 (5)	0.01551 (15)
H6'A	0.188777	0.348302	0.962284	0.019*
H6'B	0.140759	0.401462	0.884021	0.019*
C7'	0.28899 (9)	0.46115 (8)	0.90849 (5)	0.01372 (14)
C8'	0.34790 (10)	0.48320 (8)	0.82794 (5)	0.01479 (15)
H8'A	0.273601	0.533318	0.800627	0.018*
H8'B	0.410198	0.527719	0.827748	0.018*
C8A'	0.42197 (9)	0.37097 (8)	0.78865 (5)	0.01198 (13)
C9'	0.68982 (9)	0.08237 (8)	0.67210 (5)	0.01403 (14)
C10'	0.18431 (11)	0.57673 (9)	0.93786 (6)	0.02038 (18)
H10D	0.147481	0.562286	0.989187	0.031*
H10E	0.111258	0.604822	0.907374	0.031*
H10F	0.227065	0.637160	0.935860	0.031*
C11'	0.40197 (10)	0.41579 (9)	0.95718 (5)	0.01834 (17)
H11D	0.363728	0.401533	1.008245	0.028*
H11E	0.445565	0.475482	0.955834	0.028*
H11F	0.468741	0.341393	0.938564	0.028*
N11'	0.23381 (8)	0.13942 (7)	0.64850 (4)	0.01237 (12)
N12'	0.27363 (8)	0.02430 (7)	0.67587 (4)	0.01332 (13)
C13'	0.36444 (9)	0.01589 (8)	0.71992 (5)	0.01276 (14)
C14'	0.38324 (9)	0.12666 (8)	0.72139 (5)	0.01173 (13)
C15'	0.29889 (9)	0.20282 (8)	0.67452 (5)	0.01320 (14)
H15'	0.288210	0.284238	0.662630	0.016*
C16'	0.43264 (9)	−0.10117 (8)	0.75833 (5)	0.01475 (15)
H16C	0.530516	−0.114623	0.752041	0.018*
H16D	0.420694	−0.164959	0.733255	0.018*
C17'	0.38266 (9)	−0.11354 (8)	0.84158 (5)	0.01480 (15)
H17'	0.406063	−0.056508	0.867963	0.018*
C18'	0.23033 (10)	−0.08467 (10)	0.85660 (6)	0.02166 (19)
H18D	0.185330	−0.002565	0.839034	0.032*
H18E	0.202154	−0.093708	0.909902	0.032*
H18F	0.205578	−0.139190	0.830536	0.032*
C19'	0.45446 (11)	−0.23934 (9)	0.87109 (6)	0.02051 (18)
H19D	0.431693	−0.296340	0.846160	0.031*
H19E	0.425742	−0.246242	0.924482	0.031*
H19F	0.552168	−0.256378	0.861634	0.031*
C21'	0.13891 (9)	0.17986 (8)	0.59760 (5)	0.01348 (14)
C22'	0.12388 (11)	0.28727 (9)	0.55669 (5)	0.01822 (17)
H22'	0.176213	0.334178	0.563006	0.022*
C23'	0.03152 (11)	0.32499 (10)	0.50659 (6)	0.02094 (18)
H23'	0.020888	0.398243	0.478748	0.025*
C24'	−0.04542 (11)	0.25734 (10)	0.49657 (5)	0.01992 (18)
H24'	−0.108510	0.284108	0.462316	0.024*
C25'	−0.02916 (10)	0.15003 (9)	0.53721 (6)	0.01906 (17)
H25'	−0.079922	0.102393	0.529701	0.023*
C26'	0.06093 (10)	0.11146 (9)	0.58894 (6)	0.01719 (16)
H26'	0.069140	0.039534	0.617928	0.021*
O2'	0.31355 (8)	0.15590 (7)	0.90040 (4)	0.02190 (15)
N1'	0.69523 (9)	0.32195 (8)	0.64594 (5)	0.01595 (14)
H01'	0.7113 (15)	0.3871 (15)	0.6517 (9)	0.027 (4)*
H02'	0.7673 (18)	0.2640 (16)	0.6248 (10)	0.037 (5)*
N2'	0.76661 (10)	−0.00011 (8)	0.64231 (5)	0.02121 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0164 (3)	0.0098 (2)	0.0141 (3)	−0.0066 (2)	0.0010 (2)	−0.0021 (2)
C2	0.0137 (3)	0.0110 (3)	0.0121 (3)	−0.0063 (3)	−0.0020 (3)	−0.0009 (2)
C3	0.0119 (3)	0.0096 (3)	0.0133 (3)	−0.0047 (3)	−0.0010 (3)	−0.0015 (2)
C4	0.0117 (3)	0.0096 (3)	0.0128 (3)	−0.0052 (3)	−0.0021 (2)	−0.0007 (2)
C4A	0.0132 (3)	0.0100 (3)	0.0118 (3)	−0.0054 (3)	−0.0019 (2)	−0.0011 (2)
C5	0.0136 (3)	0.0142 (3)	0.0136 (3)	−0.0067 (3)	−0.0012 (3)	−0.0015 (3)
C6	0.0128 (3)	0.0151 (4)	0.0167 (3)	−0.0056 (3)	−0.0009 (3)	−0.0035 (3)
C7	0.0136 (3)	0.0125 (3)	0.0136 (3)	−0.0042 (3)	−0.0017 (3)	−0.0034 (3)
C8	0.0173 (4)	0.0108 (3)	0.0142 (3)	−0.0053 (3)	−0.0015 (3)	−0.0029 (3)
C8A	0.0142 (3)	0.0104 (3)	0.0113 (3)	−0.0058 (3)	−0.0021 (2)	−0.0006 (2)
C9	0.0154 (4)	0.0128 (3)	0.0150 (3)	−0.0065 (3)	−0.0013 (3)	−0.0002 (3)
C10	0.0189 (4)	0.0149 (4)	0.0216 (4)	−0.0038 (3)	−0.0006 (3)	−0.0071 (3)
C11	0.0163 (4)	0.0199 (4)	0.0142 (3)	−0.0065 (3)	−0.0038 (3)	−0.0024 (3)
N11	0.0155 (3)	0.0107 (3)	0.0157 (3)	−0.0065 (2)	−0.0059 (2)	−0.0003 (2)
N12	0.0152 (3)	0.0104 (3)	0.0173 (3)	−0.0060 (2)	−0.0045 (3)	−0.0010 (2)
C13	0.0133 (3)	0.0105 (3)	0.0157 (3)	−0.0060 (3)	−0.0034 (3)	−0.0010 (3)
C14	0.0131 (3)	0.0095 (3)	0.0133 (3)	−0.0052 (3)	−0.0024 (3)	−0.0009 (2)
C15	0.0163 (4)	0.0106 (3)	0.0148 (3)	−0.0069 (3)	−0.0032 (3)	−0.0016 (3)
C16	0.0154 (4)	0.0090 (3)	0.0234 (4)	−0.0042 (3)	−0.0055 (3)	−0.0005 (3)
C17	0.0198 (4)	0.0136 (4)	0.0231 (4)	−0.0084 (3)	−0.0093 (3)	0.0043 (3)
C18	0.0217 (5)	0.0328 (6)	0.0248 (5)	−0.0124 (4)	−0.0053 (4)	0.0068 (4)
C19	0.0343 (6)	0.0158 (4)	0.0408 (6)	−0.0114 (4)	−0.0217 (5)	0.0108 (4)
C21	0.0147 (3)	0.0138 (3)	0.0130 (3)	−0.0066 (3)	−0.0032 (3)	−0.0005 (3)
C22	0.0192 (4)	0.0156 (4)	0.0173 (4)	−0.0065 (3)	−0.0055 (3)	−0.0001 (3)
C23	0.0205 (4)	0.0193 (4)	0.0167 (4)	−0.0052 (3)	−0.0062 (3)	0.0019 (3)
C24	0.0184 (4)	0.0256 (5)	0.0136 (3)	−0.0086 (3)	−0.0057 (3)	0.0014 (3)
C25	0.0271 (5)	0.0221 (5)	0.0214 (4)	−0.0105 (4)	−0.0115 (4)	−0.0012 (4)
C26	0.0253 (5)	0.0174 (4)	0.0227 (4)	−0.0085 (3)	−0.0113 (4)	−0.0019 (3)
O2	0.0232 (3)	0.0154 (3)	0.0200 (3)	−0.0106 (3)	0.0036 (3)	−0.0009 (2)
N1	0.0186 (4)	0.0151 (3)	0.0189 (3)	−0.0112 (3)	0.0038 (3)	−0.0040 (3)
N2	0.0245 (4)	0.0158 (4)	0.0248 (4)	−0.0058 (3)	0.0029 (3)	−0.0043 (3)
O1'	0.0177 (3)	0.0098 (2)	0.0138 (3)	−0.0062 (2)	−0.0004 (2)	−0.0008 (2)
C2'	0.0142 (3)	0.0107 (3)	0.0121 (3)	−0.0059 (3)	−0.0024 (3)	−0.0012 (3)
C3'	0.0124 (3)	0.0100 (3)	0.0145 (3)	−0.0054 (3)	−0.0019 (3)	−0.0005 (3)
C4'	0.0133 (3)	0.0096 (3)	0.0135 (3)	−0.0051 (3)	−0.0022 (3)	−0.0011 (3)
C4A'	0.0147 (3)	0.0105 (3)	0.0120 (3)	−0.0057 (3)	−0.0027 (3)	−0.0008 (2)
C5'	0.0157 (4)	0.0138 (4)	0.0150 (3)	−0.0076 (3)	−0.0012 (3)	−0.0023 (3)
C6'	0.0138 (4)	0.0162 (4)	0.0182 (4)	−0.0070 (3)	−0.0002 (3)	−0.0046 (3)
C7'	0.0152 (4)	0.0124 (3)	0.0145 (3)	−0.0048 (3)	−0.0028 (3)	−0.0032 (3)
C8'	0.0202 (4)	0.0098 (3)	0.0145 (3)	−0.0045 (3)	−0.0032 (3)	−0.0020 (3)
C8A'	0.0144 (3)	0.0107 (3)	0.0125 (3)	−0.0058 (3)	−0.0030 (3)	−0.0008 (3)
C9'	0.0155 (4)	0.0123 (3)	0.0154 (3)	−0.0064 (3)	−0.0025 (3)	0.0006 (3)
C10'	0.0206 (4)	0.0158 (4)	0.0233 (4)	−0.0037 (3)	−0.0003 (3)	−0.0074 (3)
C11'	0.0177 (4)	0.0227 (4)	0.0162 (4)	−0.0067 (3)	−0.0058 (3)	−0.0030 (3)
N11'	0.0148 (3)	0.0097 (3)	0.0149 (3)	−0.0059 (2)	−0.0043 (2)	−0.0004 (2)
N12'	0.0144 (3)	0.0102 (3)	0.0171 (3)	−0.0055 (2)	−0.0041 (2)	−0.0003 (2)
C13'	0.0133 (3)	0.0102 (3)	0.0161 (3)	−0.0051 (3)	−0.0025 (3)	−0.0016 (3)
C14'	0.0124 (3)	0.0104 (3)	0.0139 (3)	−0.0057 (3)	−0.0017 (3)	−0.0014 (3)
C15'	0.0154 (4)	0.0108 (3)	0.0156 (3)	−0.0062 (3)	−0.0038 (3)	−0.0013 (3)
C16'	0.0152 (4)	0.0106 (3)	0.0190 (4)	−0.0046 (3)	−0.0032 (3)	−0.0014 (3)
C17'	0.0149 (4)	0.0119 (3)	0.0190 (4)	−0.0058 (3)	−0.0049 (3)	0.0010 (3)
C18'	0.0157 (4)	0.0247 (5)	0.0235 (4)	−0.0065 (4)	−0.0029 (3)	0.0027 (4)
C19'	0.0216 (4)	0.0146 (4)	0.0267 (5)	−0.0067 (3)	−0.0090 (4)	0.0043 (3)
C21'	0.0137 (3)	0.0142 (3)	0.0136 (3)	−0.0051 (3)	−0.0029 (3)	−0.0021 (3)
C22'	0.0239 (4)	0.0185 (4)	0.0154 (4)	−0.0108 (3)	−0.0056 (3)	0.0024 (3)
C23'	0.0266 (5)	0.0225 (4)	0.0157 (4)	−0.0097 (4)	−0.0083 (3)	0.0039 (3)
C24'	0.0209 (4)	0.0249 (5)	0.0149 (4)	−0.0071 (4)	−0.0065 (3)	−0.0010 (3)
C25'	0.0171 (4)	0.0212 (4)	0.0211 (4)	−0.0066 (3)	−0.0070 (3)	−0.0038 (3)
C26'	0.0172 (4)	0.0153 (4)	0.0214 (4)	−0.0070 (3)	−0.0064 (3)	0.0002 (3)
O2'	0.0289 (4)	0.0157 (3)	0.0212 (3)	−0.0114 (3)	0.0048 (3)	−0.0012 (3)
N1'	0.0194 (4)	0.0146 (3)	0.0170 (3)	−0.0106 (3)	0.0009 (3)	−0.0026 (3)
N2'	0.0231 (4)	0.0136 (3)	0.0246 (4)	−0.0049 (3)	0.0006 (3)	−0.0019 (3)

Geometric parameters (Å, º) top

O1—C2	1.3663 (11)	O1'—C2'	1.3672 (11)
O1—C8A	1.3760 (11)	O1'—C8A'	1.3736 (11)
C2—N1	1.3474 (12)	C2'—N1'	1.3505 (12)
C2—C3	1.3623 (12)	C2'—C3'	1.3629 (12)
C3—C9	1.4125 (12)	C3'—C9'	1.4158 (12)
C3—C4	1.5207 (12)	C3'—C4'	1.5206 (12)
C4—C4A	1.5085 (12)	C4'—C4A'	1.5064 (12)
C4—C14	1.5146 (12)	C4'—C14'	1.5129 (12)
C4—H4	1.0000	C4'—H4'	1.0000
C4A—C8A	1.3404 (12)	C4A'—C8A'	1.3446 (12)
C4A—C5	1.4753 (12)	C4A'—C5'	1.4744 (13)
C5—O2	1.2271 (11)	C5'—O2'	1.2244 (12)
C5—C6	1.5073 (13)	C5'—C6'	1.5086 (13)
C6—C7	1.5375 (13)	C6'—C7'	1.5388 (13)
C6—H6A	0.9900	C6'—H6'A	0.9900
C6—H6B	0.9900	C6'—H6'B	0.9900
C7—C10	1.5289 (13)	C7'—C10'	1.5287 (13)
C7—C11	1.5346 (13)	C7'—C11'	1.5349 (13)
C7—C8	1.5409 (13)	C7'—C8'	1.5401 (13)
C8—C8A	1.4924 (12)	C8'—C8A'	1.4936 (12)
C8—H8A	0.9900	C8'—H8'A	0.9900
C8—H8B	0.9900	C8'—H8'B	0.9900
C9—N2	1.1603 (13)	C9'—N2'	1.1610 (13)
C10—H10A	0.9800	C10'—H10D	0.9800
C10—H10B	0.9800	C10'—H10E	0.9800
C10—H10C	0.9800	C10'—H10F	0.9800
C11—H11A	0.9800	C11'—H11D	0.9800
C11—H11B	0.9800	C11'—H11E	0.9800
C11—H11C	0.9800	C11'—H11F	0.9800
N11—C15	1.3644 (12)	N11'—C15'	1.3627 (12)
N11—N12	1.3644 (11)	N11'—N12'	1.3631 (11)
N11—C21	1.4201 (12)	N11'—C21'	1.4206 (12)
N12—C13	1.3368 (11)	N12'—C13'	1.3371 (11)
C13—C14	1.4176 (12)	C13'—C14'	1.4183 (12)
C13—C16	1.4954 (12)	C13'—C16'	1.4999 (12)
C14—C15	1.3800 (12)	C14'—C15'	1.3809 (12)
C15—H15	0.9500	C15'—H15'	0.9500
C16—C17	1.5420 (14)	C16'—C17'	1.5408 (13)
C16—H16A	0.9900	C16'—H16C	0.9900
C16—H16B	0.9900	C16'—H16D	0.9900
C17—C19	1.5245 (14)	C17'—C19'	1.5229 (13)
C17—C18	1.5250 (15)	C17'—C18'	1.5242 (14)
C17—H17	1.0000	C17'—H17'	1.0000
C18—H18A	0.9800	C18'—H18D	0.9800
C18—H18B	0.9800	C18'—H18E	0.9800
C18—H18C	0.9800	C18'—H18F	0.9800
C19—H19A	0.9800	C19'—H19D	0.9800
C19—H19B	0.9800	C19'—H19E	0.9800
C19—H19C	0.9800	C19'—H19F	0.9800
C21—C26	1.3921 (13)	C21'—C22'	1.3943 (13)
C21—C22	1.3953 (13)	C21'—C26'	1.3971 (13)
C22—C23	1.3927 (13)	C22'—C23'	1.3900 (14)
C22—H22	0.9500	C22'—H22'	0.9500
C23—C24	1.3897 (15)	C23'—C24'	1.3878 (15)
C23—H23	0.9500	C23'—H23'	0.9500
C24—C25	1.3860 (15)	C24'—C25'	1.3897 (15)
C24—H24	0.9500	C24'—H24'	0.9500
C25—C26	1.3940 (14)	C25'—C26'	1.3955 (13)
C25—H25	0.9500	C25'—H25'	0.9500
C26—H26	0.9500	C26'—H26'	0.9500
N1—H01	0.868 (16)	N1'—H01'	0.878 (17)
N1—H02	0.886 (18)	N1'—H02'	0.899 (18)

C2—O1—C8A	118.60 (7)	C2'—O1'—C8A'	118.45 (7)
N1—C2—C3	127.39 (8)	N1'—C2'—C3'	127.81 (8)
N1—C2—O1	110.45 (7)	N1'—C2'—O1'	110.10 (8)
C3—C2—O1	122.16 (8)	C3'—C2'—O1'	122.08 (8)
C2—C3—C9	118.87 (8)	C2'—C3'—C9'	119.24 (8)
C2—C3—C4	122.98 (8)	C2'—C3'—C4'	122.79 (8)
C9—C3—C4	118.07 (7)	C9'—C3'—C4'	117.79 (7)
C4A—C4—C14	111.88 (7)	C4A'—C4'—C14'	111.68 (7)
C4A—C4—C3	108.28 (7)	C4A'—C4'—C3'	108.14 (7)
C14—C4—C3	112.35 (7)	C14'—C4'—C3'	112.21 (7)
C4A—C4—H4	108.1	C4A'—C4'—H4'	108.2
C14—C4—H4	108.1	C14'—C4'—H4'	108.2
C3—C4—H4	108.1	C3'—C4'—H4'	108.2
C8A—C4A—C5	118.36 (8)	C8A'—C4A'—C5'	118.42 (8)
C8A—C4A—C4	123.37 (8)	C8A'—C4A'—C4'	123.05 (8)
C5—C4A—C4	118.22 (7)	C5'—C4A'—C4'	118.48 (7)
O2—C5—C4A	120.32 (8)	O2'—C5'—C4A'	120.11 (8)
O2—C5—C6	122.23 (8)	O2'—C5'—C6'	122.26 (8)
C4A—C5—C6	117.45 (8)	C4A'—C5'—C6'	117.62 (8)
C5—C6—C7	112.86 (7)	C5'—C6'—C7'	112.80 (7)
C5—C6—H6A	109.0	C5'—C6'—H6'A	109.0
C7—C6—H6A	109.0	C7'—C6'—H6'A	109.0
C5—C6—H6B	109.0	C5'—C6'—H6'B	109.0
C7—C6—H6B	109.0	C7'—C6'—H6'B	109.0
H6A—C6—H6B	107.8	H6'A—C6'—H6'B	107.8
C10—C7—C11	109.22 (7)	C10'—C7'—C11'	109.48 (8)
C10—C7—C6	109.50 (7)	C10'—C7'—C6'	109.23 (8)
C11—C7—C6	109.73 (8)	C11'—C7'—C6'	109.64 (8)
C10—C7—C8	109.60 (8)	C10'—C7'—C8'	109.81 (8)
C11—C7—C8	110.03 (7)	C11'—C7'—C8'	110.00 (8)
C6—C7—C8	108.76 (7)	C6'—C7'—C8'	108.67 (7)
C8A—C8—C7	113.14 (7)	C8A'—C8'—C7'	113.06 (7)
C8A—C8—H8A	109.0	C8A'—C8'—H8'A	109.0
C7—C8—H8A	109.0	C7'—C8'—H8'A	109.0
C8A—C8—H8B	109.0	C8A'—C8'—H8'B	109.0
C7—C8—H8B	109.0	C7'—C8'—H8'B	109.0
H8A—C8—H8B	107.8	H8'A—C8'—H8'B	107.8
C4A—C8A—O1	122.88 (8)	C4A'—C8A'—O1'	122.97 (8)
C4A—C8A—C8	126.01 (8)	C4A'—C8A'—C8'	125.76 (8)
O1—C8A—C8	111.11 (7)	O1'—C8A'—C8'	111.26 (7)
N2—C9—C3	177.46 (11)	N2'—C9'—C3'	177.58 (10)
C7—C10—H10A	109.5	C7'—C10'—H10D	109.5
C7—C10—H10B	109.5	C7'—C10'—H10E	109.5
H10A—C10—H10B	109.5	H10D—C10'—H10E	109.5
C7—C10—H10C	109.5	C7'—C10'—H10F	109.5
H10A—C10—H10C	109.5	H10D—C10'—H10F	109.5
H10B—C10—H10C	109.5	H10E—C10'—H10F	109.5
C7—C11—H11A	109.5	C7'—C11'—H11D	109.5
C7—C11—H11B	109.5	C7'—C11'—H11E	109.5
H11A—C11—H11B	109.5	H11D—C11'—H11E	109.5
C7—C11—H11C	109.5	C7'—C11'—H11F	109.5
H11A—C11—H11C	109.5	H11D—C11'—H11F	109.5
H11B—C11—H11C	109.5	H11E—C11'—H11F	109.5
C15—N11—N12	111.27 (7)	C15'—N11'—N12'	111.41 (7)
C15—N11—C21	128.02 (8)	C15'—N11'—C21'	127.54 (8)
N12—N11—C21	120.68 (7)	N12'—N11'—C21'	121.01 (7)
C13—N12—N11	105.58 (7)	C13'—N12'—N11'	105.55 (7)
N12—C13—C14	110.94 (8)	N12'—C13'—C14'	110.91 (8)
N12—C13—C16	120.35 (8)	N12'—C13'—C16'	119.96 (8)
C14—C13—C16	128.71 (8)	C14'—C13'—C16'	129.11 (8)
C15—C14—C13	104.92 (7)	C15'—C14'—C13'	104.89 (8)
C15—C14—C4	127.10 (8)	C15'—C14'—C4'	126.23 (8)
C13—C14—C4	127.91 (8)	C13'—C14'—C4'	128.86 (8)
N11—C15—C14	107.28 (8)	N11'—C15'—C14'	107.23 (8)
N11—C15—H15	126.4	N11'—C15'—H15'	126.4
C14—C15—H15	126.4	C14'—C15'—H15'	126.4
C13—C16—C17	115.49 (8)	C13'—C16'—C17'	115.82 (7)
C13—C16—H16A	108.4	C13'—C16'—H16C	108.3
C17—C16—H16A	108.4	C17'—C16'—H16C	108.3
C13—C16—H16B	108.4	C13'—C16'—H16D	108.3
C17—C16—H16B	108.4	C17'—C16'—H16D	108.3
H16A—C16—H16B	107.5	H16C—C16'—H16D	107.4
C19—C17—C18	110.65 (9)	C19'—C17'—C18'	110.31 (8)
C19—C17—C16	109.24 (9)	C19'—C17'—C16'	109.42 (8)
C18—C17—C16	111.99 (8)	C18'—C17'—C16'	111.66 (8)
C19—C17—H17	108.3	C19'—C17'—H17'	108.5
C18—C17—H17	108.3	C18'—C17'—H17'	108.5
C16—C17—H17	108.3	C16'—C17'—H17'	108.5
C17—C18—H18A	109.5	C17'—C18'—H18D	109.5
C17—C18—H18B	109.5	C17'—C18'—H18E	109.5
H18A—C18—H18B	109.5	H18D—C18'—H18E	109.5
C17—C18—H18C	109.5	C17'—C18'—H18F	109.5
H18A—C18—H18C	109.5	H18D—C18'—H18F	109.5
H18B—C18—H18C	109.5	H18E—C18'—H18F	109.5
C17—C19—H19A	109.5	C17'—C19'—H19D	109.5
C17—C19—H19B	109.5	C17'—C19'—H19E	109.5
H19A—C19—H19B	109.5	H19D—C19'—H19E	109.5
C17—C19—H19C	109.5	C17'—C19'—H19F	109.5
H19A—C19—H19C	109.5	H19D—C19'—H19F	109.5
H19B—C19—H19C	109.5	H19E—C19'—H19F	109.5
C26—C21—C22	120.11 (8)	C22'—C21'—C26'	120.39 (8)
C26—C21—N11	119.82 (8)	C22'—C21'—N11'	120.02 (8)
C22—C21—N11	120.06 (8)	C26'—C21'—N11'	119.59 (8)
C23—C22—C21	119.44 (9)	C23'—C22'—C21'	119.29 (9)
C23—C22—H22	120.3	C23'—C22'—H22'	120.4
C21—C22—H22	120.3	C21'—C22'—H22'	120.4
C24—C23—C22	120.64 (9)	C24'—C23'—C22'	121.06 (10)
C24—C23—H23	119.7	C24'—C23'—H23'	119.5
C22—C23—H23	119.7	C22'—C23'—H23'	119.5
C25—C24—C23	119.60 (9)	C23'—C24'—C25'	119.27 (9)
C25—C24—H24	120.2	C23'—C24'—H24'	120.4
C23—C24—H24	120.2	C25'—C24'—H24'	120.4
C24—C25—C26	120.43 (10)	C24'—C25'—C26'	120.72 (9)
C24—C25—H25	119.8	C24'—C25'—H25'	119.6
C26—C25—H25	119.8	C26'—C25'—H25'	119.6
C21—C26—C25	119.76 (9)	C25'—C26'—C21'	119.24 (9)
C21—C26—H26	120.1	C25'—C26'—H26'	120.4
C25—C26—H26	120.1	C21'—C26'—H26'	120.4
C2—N1—H01	121.3 (10)	C2'—N1'—H01'	119.6 (11)
C2—N1—H02	120.3 (12)	C2'—N1'—H02'	118.3 (12)
H01—N1—H02	116.3 (15)	H01'—N1'—H02'	114.0 (15)

C8A—O1—C2—N1	−172.40 (8)	C8A'—O1'—C2'—N1'	−172.34 (8)
C8A—O1—C2—C3	8.30 (12)	C8A'—O1'—C2'—C3'	8.38 (12)
N1—C2—C3—C9	−0.17 (14)	N1'—C2'—C3'—C9'	0.87 (14)
O1—C2—C3—C9	179.01 (8)	O1'—C2'—C3'—C9'	−179.98 (8)
N1—C2—C3—C4	−177.01 (9)	N1'—C2'—C3'—C4'	−174.29 (9)
O1—C2—C3—C4	2.16 (13)	O1'—C2'—C3'—C4'	4.85 (13)
C2—C3—C4—C4A	−11.67 (11)	C2'—C3'—C4'—C4A'	−15.29 (11)
C9—C3—C4—C4A	171.46 (8)	C9'—C3'—C4'—C4A'	169.48 (8)
C2—C3—C4—C14	112.40 (9)	C2'—C3'—C4'—C14'	108.34 (9)
C9—C3—C4—C14	−64.47 (10)	C9'—C3'—C4'—C14'	−66.90 (10)
C14—C4—C4A—C8A	−111.84 (9)	C14'—C4'—C4A'—C8A'	−109.20 (10)
C3—C4—C4A—C8A	12.51 (11)	C3'—C4'—C4A'—C8A'	14.75 (11)
C14—C4—C4A—C5	70.80 (10)	C14'—C4'—C4A'—C5'	73.12 (10)
C3—C4—C4A—C5	−164.85 (7)	C3'—C4'—C4A'—C5'	−162.94 (8)
C8A—C4A—C5—O2	−165.26 (9)	C8A'—C4A'—C5'—O2'	−166.71 (9)
C4—C4A—C5—O2	12.24 (13)	C4'—C4A'—C5'—O2'	11.09 (13)
C8A—C4A—C5—C6	15.18 (12)	C8A'—C4A'—C5'—C6'	14.24 (12)
C4—C4A—C5—C6	−167.32 (7)	C4'—C4A'—C5'—C6'	−167.97 (8)
O2—C5—C6—C7	139.75 (9)	O2'—C5'—C6'—C7'	141.01 (10)
C4A—C5—C6—C7	−40.70 (11)	C4A'—C5'—C6'—C7'	−39.95 (11)
C5—C6—C7—C10	173.93 (8)	C5'—C6'—C7'—C10'	174.16 (8)
C5—C6—C7—C11	−66.21 (10)	C5'—C6'—C7'—C11'	−65.89 (10)
C5—C6—C7—C8	54.19 (10)	C5'—C6'—C7'—C8'	54.37 (10)
C10—C7—C8—C8A	−163.90 (8)	C10'—C7'—C8'—C8A'	−164.55 (8)
C11—C7—C8—C8A	75.99 (10)	C11'—C7'—C8'—C8A'	74.90 (10)
C6—C7—C8—C8A	−44.22 (10)	C6'—C7'—C8'—C8A'	−45.13 (10)
C5—C4A—C8A—O1	173.49 (8)	C5'—C4A'—C8A'—O1'	173.95 (8)
C4—C4A—C8A—O1	−3.87 (13)	C4'—C4A'—C8A'—O1'	−3.73 (13)
C5—C4A—C8A—C8	−5.90 (13)	C5'—C4A'—C8A'—C8'	−5.65 (13)
C4—C4A—C8A—C8	176.74 (8)	C4'—C4A'—C8A'—C8'	176.66 (8)
C2—O1—C8A—C4A	−7.55 (12)	C2'—O1'—C8A'—C4A'	−9.07 (12)
C2—O1—C8A—C8	171.92 (7)	C2'—O1'—C8A'—C8'	170.59 (7)
C7—C8—C8A—C4A	21.95 (13)	C7'—C8'—C8A'—C4A'	22.65 (13)
C7—C8—C8A—O1	−157.51 (7)	C7'—C8'—C8A'—O1'	−156.99 (7)
C15—N11—N12—C13	0.42 (10)	C15'—N11'—N12'—C13'	0.31 (10)
C21—N11—N12—C13	178.71 (8)	C21'—N11'—N12'—C13'	178.48 (8)
N11—N12—C13—C14	0.19 (10)	N11'—N12'—C13'—C14'	0.26 (10)
N11—N12—C13—C16	−179.64 (8)	N11'—N12'—C13'—C16'	−178.52 (8)
N12—C13—C14—C15	−0.71 (10)	N12'—C13'—C14'—C15'	−0.70 (10)
C16—C13—C14—C15	179.11 (9)	C16'—C13'—C14'—C15'	177.93 (9)
N12—C13—C14—C4	−177.87 (8)	N12'—C13'—C14'—C4'	−178.74 (8)
C16—C13—C14—C4	1.95 (15)	C16'—C13'—C14'—C4'	−0.11 (15)
C4A—C4—C14—C15	49.07 (12)	C4A'—C4'—C14'—C15'	53.24 (12)
C3—C4—C14—C15	−72.98 (11)	C3'—C4'—C14'—C15'	−68.38 (11)
C4A—C4—C14—C13	−134.37 (9)	C4A'—C4'—C14'—C13'	−129.11 (9)
C3—C4—C14—C13	103.58 (10)	C3'—C4'—C14'—C13'	109.27 (10)
N12—N11—C15—C14	−0.87 (10)	N12'—N11'—C15'—C14'	−0.75 (10)
C21—N11—C15—C14	−179.01 (9)	C21'—N11'—C15'—C14'	−178.78 (8)
C13—C14—C15—N11	0.92 (10)	C13'—C14'—C15'—N11'	0.85 (10)
C4—C14—C15—N11	178.12 (8)	C4'—C14'—C15'—N11'	178.96 (8)
N12—C13—C16—C17	−106.58 (10)	N12'—C13'—C16'—C17'	−104.43 (10)
C14—C13—C16—C17	73.62 (12)	C14'—C13'—C16'—C17'	77.05 (12)
C13—C16—C17—C19	179.89 (8)	C13'—C16'—C17'—C19'	176.15 (8)
C13—C16—C17—C18	56.94 (11)	C13'—C16'—C17'—C18'	53.73 (11)
C15—N11—C21—C26	163.71 (10)	C15'—N11'—C21'—C22'	13.50 (14)
C15—N11—C21—C22	−15.34 (15)	N12'—N11'—C21'—C22'	−164.36 (9)
N12—N11—C21—C22	166.67 (8)	C15'—N11'—C21'—C26'	−166.43 (9)
N12—N11—C21—C26	−14.27 (13)	N12'—N11'—C21'—C26'	15.71 (13)
C26—C21—C22—C23	1.47 (15)	C26'—C21'—C22'—C23'	−0.70 (15)
N11—C21—C22—C23	−179.48 (9)	N11'—C21'—C22'—C23'	179.37 (9)
C21—C22—C23—C24	−0.53 (15)	C21'—C22'—C23'—C24'	−0.18 (16)
C22—C23—C24—C25	−0.64 (16)	C22'—C23'—C24'—C25'	−0.24 (16)
C23—C24—C25—C26	0.88 (17)	C23'—C24'—C25'—C26'	1.56 (15)
C22—C21—C26—C25	−1.23 (16)	C24'—C25'—C26'—C21'	−2.42 (15)
N11—C21—C26—C25	179.71 (10)	C22'—C21'—C26'—C25'	1.99 (14)
C24—C25—C26—C21	0.05 (17)	N11'—C21'—C26'—C25'	−178.09 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1′—H01′···N12	0.878 (17)	2.115 (17)	2.9895 (11)	173.5 (14)
N1—H01···N12′ⁱ	0.868 (16)	2.145 (16)	3.0071 (11)	172.0 (15)
C15—H15···N2′ⁱⁱ	0.95	2.41	3.3622 (13)	176
C15′—H15′···N2ⁱⁱⁱ	0.95	2.43	3.3816 (13)	180
C11—H11A···O2′^iv	0.98	2.47	3.3965 (12)	157
C11′—H11D···O2^iv	0.98	2.59	3.5046 (13)	155

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

Acknowledgements

The authors acknowledge support by the Open Access Publication Funds of the Technical University of Braunschweig.

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