Stereochemistry of the methyl­idene-bridged quinazoline-iso­quinoline alkaloid 3-{[6,7-dimeth­oxy-1-(4-nitro­phen­yl)-1,2,3,4-tetra­hydro­isoquinolin-2-yl]methyl­idene}-1,2,3,9-tetra­hydro­pyrrolo­[2,1-b]quinazolin-9-one methanol monosolvate

Tojiboev, A.; Zhurakulov, S.; Vinogradova, V.; Englert, U.; Wang, R.

doi:10.1107/S2056989020006696

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ISSN: 2056-9890

Volume 76| Part 6| June 2020| Pages 914-919

https://doi.org/10.1107/S2056989020006696

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Stereochemistry of the methylidene-bridged quinazoline-isoquinoline alkaloid 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one methanol monosolvate

Akmal Tojiboev,^a ^* Sherzod Zhurakulov,^b Valentina Vinogradova,^b Ulli Englert ^c and Ruimin Wang ^c

^aLaboratory of Thermophysics of Multiphase Systems, Institute of Ion-Plasm and Laser Technologies named after U.A. Arifov, Academy of Sciences of Uzbekistan,100125, Durmon yuli st. 33, Tashkent, Uzbekistan, ^bS.Yunusov Institute of Chemistry of Plant Substances, Academy of Science of, Uzbekistan, Mirzo Ulugbek Str. 77, 100170 Tashkent, Uzbekistan, and ^cInstitute of Inorganic Chemistry, RWTH Aachen University, Landoltweg 1, 52056, Aachen, Germany
^*Correspondence e-mail: a_tojiboev@yahoo.com

Edited by L. Fabian, University of East Anglia, England (Received 5 February 2020; accepted 19 May 2020; online 22 May 2020)

Two potentially bioactive fragments, namely a tricyclic quinazoline derivative with an exocyclic alkene moiety and a substituted isoquinoline, are coupled to give 3-{[6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one. The target product crystallizes as a methanol solvate, C₂₉H₂₆N₄O₅·CH₄O, and is E configured. The alternative Z isomer would necessarily imply either considerable twist about the central double bond or very unfavourable intramolecular contacts between sterically more demanding substituents. The main residue and the co-crystallized solvent molecule aggregate to discrete pairs via a classical O—H⋯O hydrogen bond with a distance of 2.8581 (7) Å between the methanol OH donor and the quinazolinone O=C acceptor.

Keywords: quinazoline; isoquinoline; steric congestion; hydrogen bonding; crystal structure.

CCDC reference: 2004621

1. Chemical context

The synthesis of the title compound, 3-[1′-(4′′-nitrophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-yl)]-methylidene-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one methanol solvate, (III) is shown in Fig. 1. It combines two well-known bioactive scaffolds, namely a tricyclic quinazoline derivative (I) and a substituted isoquinoline (II).

Figure 1
Chemical scheme showing the synthesis of the title compound

Tricyclic quinazoline alkaloids are frequently encountered in nature (Michael, 1997 ; Eguchi, 2006 ; Shakhidoyatov et al., 2014 ). The reason for the wide interest in studying these substances lies in their multi-facetted biological activity: they have been associated with antibacterial (Jantova et al., 2004 ), tumor growth-inhibiting (Aoyagi et al., 1999 ; Kuneš et al., 2000 ; Foster et al., 1999 ; Forsch et al., 2002 ; Abdel-Jalil et al., 2005 ), antifungal (Dandia et al., 2005 ; Nikhil et al., 2011 ), antihyperglycemic (Ram et al., 2003 ) and anti-inflammatory (Yeh-Long et al., 2004 ) activity. They have been used as a bronchodilator (Jindal et al., 2002 ), cholinesterase inhibitor (Decker, 2005 ), antifolate (Rosowsky et al., 2000 ) and as a protein kinase inhibitor (Levitzki et al., 2003 ). Additional reports suggest these derivatives are used as anti-cancer (Manoj et al., 2013 ), anti-HIV (Zaigang et al., 2009 ), anticonvulsant and antihypertensive (Muruganantham et al., 2004 ) drugs and as antioxidants (Srinubabu et al., 2014 ). The Cambridge Structural Database (CSD, version 5.40, update February 2019; Groom et al., 2016 ) contains 118 structurally characterized substituted tricyclic quinazolines. Different methods for their efficient synthesis have been developed (Bowman et al., 2007 ; Deetz et al., 2001 ; Kamal et al., 2001 , 2004 ; Lee et al., 2003 ; Liu et al., 2005 ). The reactive centres in the tricyclic quinazoline scaffold allow for further derivatization via electrophilic or nucleophiles substitution.

Isoquinoline alkaloids represent a particularly popular and widespread group of alkaloids. Even for fairly simple isoquinoline derivatives, biological activity has been reported. Examples include analgetic, anti-inflammatory and anti-cancer properties (Jeetah et al., 2014 ), anti-AIDS (Uesawa et al., 2011 ), antifungal activity (Kashiwada et al., 2005 ) and cardiovascular effects (Candenas et al., 1990 ). Antagonists for the pathogenesis of neurological diseases, such as Parkinson's disease (Zaima et al., 2012 ) have also been described. A group of synthetic 1-aryltetrahydroisoquinoline derivatives show antiepileptic (Gitto et al., 2003 ), analgesic (Tursunkhodzhaeva et al., 2012 ) and sedative-anxiolytic activity (Mirzaev et al., 2017 ).

Over the years the synthetic interest in the quest for new isoquinoline derivatives has not declined (Bentley, 2006 ; Zhurakulov et al., 2013 , 2014 , 2015 ), because even minor changes in the molecular geometry may lead to improved therapeutic effects. Both moieties mentioned above, a quinazoline and an isoquinoline, have been successfully connected by a methylidene bridge (Elmuradov et al., 1998 , 2008 ; Turdibayev et al., 2011 ; Zhurakulov et al., 2015). This coupling reaction allows two potentially bioactive components to be combined in a single molecule. In view of the high chemical and biological activity of isoquinoline and tricyclic quinazoline alkaloids, we expect that the combination of both scaffolds as in the target compound of the present study could lead to unprecedented properties.

2. Structural commentary

The title compound crystallizes in the monoclinic space group P2₁/n with one molecule of the target heterocycle and one molecule of methanol in the asymmetric unit. A displacement ellipsoid plot and the numbering scheme for both molecules are provided in Fig. 2.

Figure 2
Displacement ellipsoid plot (Spek, 2020

) of the asymmetric unit of 3-[1′-(4′′-nitrophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinol-2-yl)]methylidene-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one with the methanol solvate and atom-labelling scheme. Ellipsoids are drawn at 50% probability, H atoms are shown as spheres of arbitrary radius.

The methoxy substituents associated with O1 and O2 are displaced slightly out of the mean plane defined by the aromatic ring in the dihydroisoquinoline moiety (C4A–C8A), with out-of-plane distances of 0.082 (3) Å for C9 and 0.221 (3) Å for C10. The twist conformation of the heterocyclic ring of the dihydroisoquinoline moiety and the equatorial position of the nitrophenyl substituent observed here are similar to those in related structures (Olszak et al., 1996 ; Turgunov et al., 2016 ). C1, C4, C4A and C8A are coplanar within error, whereas C3 and N2 are on opposite sides of this plane. The nitrophenyl substituent C11–C16 and the aromatic part of the dihydroisoquinoline (C4A–C8A) form an angle of 75.70 (14)°. The main motivation for our crystallographic study was to establish the configuration about the C17=C18 double bond. Intuition suggests that the E configuration should clearly be favoured, and our experiment confirms this expectation. In order to further explore the steric congestion of an alternative Z configuration, we generated such a hypothetical molecule by 180° rotation of the complete tricyclic quinazoline moiety about C17=C18. The resulting geometry is depicted in Fig. 3.

Figure 3
Ball and stick representation (Spek, 2020

) of a hypothetical Z-configured molecule generated by 180° rotation of all atoms of the tricyclic quinazoline moiety about the C17=C18 bond; the dashed red line emphasizes the unfavourable intramolecular contact (see text).

The prohibitively short intramolecular contact between N19 and C3, shown as a dashed red line, amounts to only 2.05 Å without taking the hydrogen atoms attached to C3 into account. If the two parts of the target molecule are perceived as at least moderately rigid groups, such an alternative Z configuration can safely be excluded. It is important to note, however, that this construction of a hypothetical Z-configured molecule relies on the experimentally established geometry of the semi-rigid isoquinoline and quinazoline moieties. The tricyclic quinazoline system, formed by three fused rings, shows deviations from planarity for the sp³ carbon atoms, with maximum displacements of 0.126 (3) Å for C26 and 0.110 (3) Å for C25 on opposite sides of the mean plane.

3. Supramolecular features

An O⋯H—O hydrogen bond links the co-crystallized methanol molecule to the keto group of the quinazoline moiety and gives rise to a D(2) graph-set motif (Table 1). Additional short contacts involve non-classical C—H⋯O interactions, with H⋯O distances ranging between 2.29 and 2.59 Å, forming a complex three-dimensional network (Table 1, Fig. 4).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯O5	0.96	1.91	2.8581 (7)	171
C1—H1⋯O1ⁱ	1.00	2.55	3.4040 (8)	143
C1—H1⋯O2ⁱ	1.00	2.37	3.2444 (8)	146
C4—H4A⋯O5ⁱⁱ	0.99	2.45	3.4346 (8)	172
C15—H15⋯O1ⁱⁱⁱ	0.95	2.44	3.3402 (8)	159
C16—H16⋯O2ⁱⁱⁱ	0.95	2.59	3.3246 (8)	134
C25—H25A⋯O4^iv	0.99	2.29	3.1224 (8)	141
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 4
Crystal packing in a view along the b axis. O—H⋯O bonds are shown as black, C—H⋯O contacts as blue dashed lines. The dark-blue dotted line indicates a stacking interaction.

Stacking (Fig. 5) occurs between the pyrrole rings of neighbouring molecules about a centre of inversion [symmetry code: (i) 1 − x, 1 − y, 1 − z], with a distance between the centroids Cg1⋯Cg1ⁱ of 3.832 (2) Å and a ring slippage of 1.246 Å. Both short intermolecular contacts together lead to a supramolecular layer structure parallel to the (010) plane.

Figure 5
View approximately along the c axis, showing stacking between the pyrrole rings (dashed dark-blue lines). The O—H⋯O hydrogen bond is shown in light blue, other hydrogen atoms have been omitted.

4. Hirshfeld surface analysis

The Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ) and the associated two-dimensional (2D) fingerprint plot (McKinnon et al., 2007 ) were performed with CrystalExplorer17 (Turner et al., 2017 ). The Hirshfeld surface for the main molecule in III, mapped with d_norm and its interaction with the co-crystallized solvent molecule is represented in Fig. 6. Colours on the Hirshfeld surface encode contact distances (red - close, white - medium, blue - long) between atoms on either side of the surface. The most obvious intermolecular interaction, the classical O⋯H—O hydrogen bond, shows up as a prominent deep-red spot on the surface, oriented towards the co-crystallized methanol molecule. The less-pronounced red features on the surface are associated with C—H⋯O contacts. Fig. 7 shows a 2D fingerprint plot for the contacts between O and H atoms. These contacts are responsible for the short lateral `spikes' on either side of the main diagonal of the plot.

Figure 6
View of the three-dimensional Hirshfeld surface of III mapped with d_norm.

Figure 7
Two-dimensional fingerprint plots for III, showing O⋯H/H⋯O interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface contacts.

5. Database survey

A search in the Cambridge Structural Database (CSD, version 5.40, update February 2019; Groom et al., 2016) gave seven occurrences of molecules containing the 3-methylidene-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one moiety with a similar planar conformation as in the title structure. A search for the 1′-(4′′-nitrophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-yl moiety gave only three hits with similar conformations for the isoquinoline fragment: 1-(4-nitrophenyl)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (ABUTIA01; Allef et al., 2007 ) and two additional structures with a chloro-substituted phenyl ring, namely 2-acetyl-1(R)-(4′-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (ADOCUS; Gitto et al., 2007 ) and N-acetyl-1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (LEFFIM; Gao et al., 2006 ).

6. Synthesis and crystallization

3-Hydroxymethylidene-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one (I) was synthesized according to the method of Oripov et al. (1979 ). Compound III was obtained from reaction of 1-(4′-nitrophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (0.164 g, 0.522 mmol) with 3-hydroxymethylidene-1,2,3,4-tetrahydropyrrolo[2,1-b]-quinazolin-9-one (0.122 g, 0.522 mmol). Yield 0.22 g, 86%; m.p. 462–465 K (after crystallization from methanol), R_f 0.81 (CHCl₃/MeOH 14:1). A detailed report on the synthesis of III and its characterization by NMR, IR and mass spectrometry is available (Zhurakulov et al., 2015). Crystals suitable for X-ray diffraction were obtained from a solution in methanol by slow evaporation of the solvent at room temperature.

7. Refinement details

Crystal data, data collection parameters and refinement results are summarized in Table 2. H atoms on C atoms were positioned geometrically and treated as riding on their parent atoms, with C—H = 0.95 (aromatic), 0.98 (methyl), 0.99 (methylene) or 1.00 Å (tertiary C atom) and were refined with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) otherwise. The H atom in the hydroxy group of the co-crystallized methanol was refined with a distance restraint [target distance O—H = 0.84 (2) Å] and with U_iso(H) = 1.2U_eq(O). The anisotropic displacement parameters of N1 and O3 atom were subjected to an enhanced rigid-bond restraint (Thorn et al., 2012 ).

Table 2
Experimental details

Crystal data
Chemical formula	C₂₉H₂₆N₄O₅·CH₄O
M_r	542.58
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	16.326 (4), 8.0566 (19), 20.565 (5)
β (°)	104.497 (6)
V (Å³)	2618.9 (11)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.55 × 0.09 × 0.08

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008 )
T_min, T_max	0.665, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	25889, 4821, 2918
R_int	0.114
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.164, 1.04
No. of reflections	4821
No. of parameters	367
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.35
Computer programs: APEX2 (Bruker, 2001 ), SAINT-Plus (Bruker, 2009 ), SHELXT (Sheldrick, 2015 ), SHELXL2014/7 (Sheldrick, 2015), PLATON (Spek, 2020 ), publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2004621

Crystal structure: contains datablocks I, test. DOI: https://doi.org/10.1107/S2056989020006696/fy2144sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020006696/fy2144Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989020006696/fy2144Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

3-{[6,7-Dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinolin-2-yl]methylidene}-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-9-one methanol monosolvate top

Crystal data top

C₂₉H₂₆N₄O₅·CH₄O	F(000) = 1144
M_r = 542.58	D_x = 1.376 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 16.326 (4) Å	Cell parameters from 1353 reflections
b = 8.0566 (19) Å	θ = 3.0–19.8°
c = 20.565 (5) Å	µ = 0.10 mm⁻¹
β = 104.497 (6)°	T = 100 K
V = 2618.9 (11) Å³	Rod, yellow
Z = 4	0.55 × 0.09 × 0.08 mm

Data collection top

Bruker APEX CCD diffractometer	4821 independent reflections
Radiation source: microsource	2918 reflections with I > 2σ(I)
Multilayer optics monochromator	R_int = 0.114
ω scans	θ_max = 25.4°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −19→19
T_min = 0.665, T_max = 0.745	k = −9→9
25889 measured reflections	l = −24→24

Refinement top

Refinement on F²	4 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.164	w = 1/[σ²(F_o²) + (0.0677P)² + 0.4688P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4821 reflections	Δρ_max = 0.39 e Å⁻³
367 parameters	Δρ_min = −0.35 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
O1	0.08305 (12)	1.1111 (2)	0.65060 (10)	0.0267 (5)
O2	0.14565 (12)	1.0007 (2)	0.77066 (9)	0.0256 (5)
O4	0.71000 (15)	1.2323 (3)	0.94869 (12)	0.0522 (7)
O3	0.60907 (14)	1.4105 (3)	0.94156 (11)	0.0385 (6)
O5	0.70612 (13)	0.3657 (3)	0.50686 (10)	0.0303 (5)
N1	0.63699 (17)	1.2806 (4)	0.92532 (13)	0.0338 (7)
N2	0.46055 (15)	0.8631 (3)	0.66495 (12)	0.0238 (6)
N19	0.59083 (15)	0.4135 (3)	0.66290 (12)	0.0260 (6)
N24A	0.62119 (15)	0.5026 (3)	0.56116 (12)	0.0241 (6)
C1	0.42173 (18)	0.8773 (4)	0.72189 (14)	0.0221 (7)
H1	0.4208	0.7639	0.7415	0.026*
C3	0.44128 (19)	1.0014 (4)	0.61757 (15)	0.0266 (7)
H3B	0.4754	0.9925	0.5841	0.032*
H3A	0.4551	1.1081	0.6418	0.032*
C4	0.34774 (18)	0.9951 (4)	0.58261 (14)	0.0269 (7)
H4B	0.3321	1.0936	0.5534	0.032*
H4A	0.3356	0.8947	0.5540	0.032*
C4A	0.29609 (19)	0.9915 (4)	0.63407 (14)	0.0236 (7)
C5	0.21208 (19)	1.0482 (4)	0.61679 (15)	0.0248 (7)
H5	0.1879	1.0853	0.5723	0.030*
C6	0.16455 (18)	1.0508 (4)	0.66287 (15)	0.0237 (7)
C7	0.19881 (18)	0.9950 (3)	0.72862 (14)	0.0226 (7)
C8	0.28131 (19)	0.9378 (3)	0.74592 (14)	0.0226 (7)
H8	0.3048	0.8982	0.7902	0.027*
C8A	0.33064 (18)	0.9374 (3)	0.69924 (14)	0.0213 (7)
C9	0.0470 (2)	1.1711 (4)	0.58366 (15)	0.0331 (8)
H9B	0.0804	1.2652	0.5743	0.050*
H9C	−0.0114	1.2071	0.5798	0.050*
H9A	0.0474	1.0821	0.5513	0.050*
C10	0.1823 (2)	0.9721 (4)	0.84092 (15)	0.0346 (9)
H10B	0.2047	0.8588	0.8474	0.052*
H10C	0.1389	0.9865	0.8659	0.052*
H10A	0.2283	1.0515	0.8574	0.052*
C11	0.47684 (18)	0.9873 (4)	0.77600 (14)	0.0213 (7)
C12	0.55019 (19)	0.9188 (4)	0.81757 (15)	0.0279 (8)
H12	0.5636	0.8057	0.8123	0.033*
C13	0.6034 (2)	1.0145 (4)	0.86629 (15)	0.0297 (8)
H13	0.6534	0.9687	0.8945	0.036*
C14	0.58186 (19)	1.1787 (4)	0.87291 (15)	0.0258 (7)
C15	0.51115 (19)	1.2512 (4)	0.83252 (14)	0.0262 (7)
H15	0.4986	1.3649	0.8375	0.031*
C16	0.45834 (19)	1.1526 (4)	0.78389 (14)	0.0256 (7)
H16	0.4087	1.1997	0.7556	0.031*
C17	0.50221 (18)	0.7246 (4)	0.65647 (15)	0.0223 (7)
H17	0.5061	0.6442	0.6909	0.027*
C18	0.53988 (18)	0.6787 (4)	0.60744 (15)	0.0238 (7)
C18A	0.58472 (18)	0.5214 (4)	0.61466 (14)	0.0223 (7)
C19A	0.64138 (18)	0.2763 (4)	0.66009 (15)	0.0239 (7)
C20	0.6513 (2)	0.1578 (4)	0.71145 (16)	0.0303 (8)
H20	0.6216	0.1704	0.7454	0.036*
C21	0.7038 (2)	0.0237 (4)	0.71301 (17)	0.0381 (9)
H21	0.7100	−0.0558	0.7480	0.046*
C22	0.7478 (2)	0.0034 (5)	0.66366 (18)	0.0440 (10)
H22	0.7848	−0.0886	0.6657	0.053*
C23	0.7382 (2)	0.1152 (4)	0.61231 (17)	0.0343 (8)
H23	0.7675	0.0995	0.5783	0.041*
C23A	0.68515 (18)	0.2530 (4)	0.60979 (15)	0.0258 (7)
C24	0.67353 (18)	0.3723 (4)	0.55492 (15)	0.0250 (7)
C25	0.59868 (19)	0.6360 (4)	0.51134 (15)	0.0279 (8)
H25B	0.5610	0.5943	0.4690	0.033*
H25A	0.6499	0.6847	0.5014	0.033*
C26	0.55278 (19)	0.7643 (4)	0.54499 (14)	0.0262 (7)
H26A	0.5876	0.8656	0.5571	0.031*
H26B	0.4978	0.7955	0.5146	0.031*
C27	0.8885 (3)	0.3496 (6)	0.4479 (2)	0.0611 (12)
H27A	0.9489	0.3688	0.4521	0.092*
H27B	0.8599	0.3294	0.4007	0.092*
H27C	0.8814	0.2527	0.4748	0.092*
O6	0.85271 (16)	0.4911 (3)	0.47115 (13)	0.0523 (7)
H6	0.8044 (18)	0.458 (5)	0.4864 (18)	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0260 (12)	0.0294 (13)	0.0210 (11)	0.0026 (10)	−0.0010 (9)	0.0009 (10)
O2	0.0272 (12)	0.0292 (13)	0.0193 (11)	0.0022 (10)	0.0034 (9)	0.0007 (10)
O4	0.0356 (15)	0.0495 (17)	0.0555 (17)	−0.0046 (13)	−0.0185 (13)	0.0101 (14)
O3	0.0387 (14)	0.0441 (16)	0.0304 (13)	−0.0057 (12)	0.0045 (11)	−0.0113 (12)
O5	0.0311 (12)	0.0356 (14)	0.0269 (12)	−0.0003 (10)	0.0123 (10)	−0.0025 (11)
N1	0.0309 (17)	0.0416 (19)	0.0256 (16)	−0.0090 (14)	0.0007 (13)	0.0040 (14)
N2	0.0272 (14)	0.0218 (15)	0.0218 (14)	0.0028 (12)	0.0054 (11)	0.0016 (12)
N19	0.0301 (15)	0.0237 (15)	0.0247 (15)	0.0019 (12)	0.0076 (12)	0.0005 (12)
N24A	0.0232 (14)	0.0241 (15)	0.0235 (14)	0.0000 (12)	0.0032 (11)	0.0004 (12)
C1	0.0255 (16)	0.0211 (17)	0.0191 (16)	0.0013 (13)	0.0047 (13)	0.0037 (14)
C3	0.0306 (18)	0.0245 (19)	0.0249 (17)	0.0010 (15)	0.0070 (14)	0.0035 (15)
C4	0.0306 (18)	0.0263 (19)	0.0219 (17)	−0.0025 (15)	0.0029 (14)	−0.0001 (15)
C4A	0.0318 (18)	0.0168 (17)	0.0211 (17)	−0.0018 (14)	0.0047 (14)	−0.0020 (14)
C5	0.0304 (18)	0.0218 (18)	0.0185 (16)	−0.0018 (14)	−0.0012 (14)	−0.0003 (14)
C6	0.0239 (17)	0.0189 (17)	0.0235 (17)	−0.0003 (14)	−0.0029 (14)	0.0006 (14)
C7	0.0268 (18)	0.0162 (16)	0.0233 (17)	−0.0028 (14)	0.0036 (14)	−0.0006 (14)
C8	0.0331 (18)	0.0146 (16)	0.0168 (16)	−0.0017 (14)	0.0002 (14)	−0.0009 (13)
C8A	0.0230 (16)	0.0158 (16)	0.0213 (17)	−0.0038 (13)	−0.0016 (13)	−0.0025 (13)
C9	0.0310 (18)	0.039 (2)	0.0235 (18)	0.0068 (16)	−0.0032 (15)	−0.0002 (16)
C10	0.039 (2)	0.043 (2)	0.0218 (18)	0.0109 (17)	0.0081 (15)	0.0058 (16)
C11	0.0216 (16)	0.0244 (18)	0.0172 (16)	−0.0012 (13)	0.0037 (13)	0.0020 (14)
C12	0.0292 (18)	0.0254 (19)	0.0283 (18)	0.0042 (15)	0.0061 (15)	0.0049 (15)
C13	0.0260 (18)	0.032 (2)	0.0265 (18)	−0.0008 (15)	−0.0017 (14)	0.0081 (16)
C14	0.0252 (17)	0.030 (2)	0.0207 (17)	−0.0049 (14)	0.0021 (14)	−0.0015 (15)
C15	0.0281 (18)	0.0268 (19)	0.0236 (17)	0.0010 (15)	0.0063 (15)	−0.0001 (15)
C16	0.0257 (17)	0.0284 (19)	0.0214 (17)	−0.0017 (15)	0.0034 (14)	0.0014 (15)
C17	0.0230 (16)	0.0179 (17)	0.0235 (17)	−0.0009 (13)	0.0011 (14)	0.0011 (14)
C18	0.0225 (16)	0.0240 (18)	0.0242 (17)	−0.0027 (13)	0.0044 (14)	−0.0005 (14)
C18A	0.0199 (16)	0.0237 (18)	0.0226 (17)	−0.0038 (13)	0.0038 (13)	−0.0040 (14)
C19A	0.0203 (16)	0.0202 (18)	0.0290 (18)	−0.0054 (13)	0.0023 (14)	−0.0048 (15)
C20	0.0304 (18)	0.033 (2)	0.0269 (18)	0.0010 (16)	0.0062 (15)	−0.0002 (16)
C21	0.043 (2)	0.037 (2)	0.035 (2)	0.0123 (17)	0.0106 (17)	0.0080 (17)
C22	0.048 (2)	0.042 (2)	0.043 (2)	0.0239 (19)	0.0138 (19)	0.0072 (19)
C23	0.037 (2)	0.034 (2)	0.034 (2)	0.0098 (16)	0.0120 (16)	0.0017 (17)
C23A	0.0213 (16)	0.0265 (18)	0.0282 (18)	0.0010 (14)	0.0036 (14)	−0.0012 (15)
C24	0.0207 (16)	0.0246 (18)	0.0279 (18)	−0.0036 (14)	0.0025 (14)	−0.0063 (15)
C25	0.0280 (17)	0.032 (2)	0.0231 (17)	−0.0015 (15)	0.0052 (14)	0.0017 (15)
C26	0.0265 (17)	0.0252 (18)	0.0260 (18)	−0.0002 (14)	0.0049 (14)	0.0027 (15)
C27	0.060 (3)	0.072 (3)	0.048 (3)	0.019 (2)	0.007 (2)	−0.011 (2)
O6	0.0492 (17)	0.0592 (19)	0.0511 (17)	−0.0084 (14)	0.0174 (14)	−0.0151 (14)

Geometric parameters (Å, º) top

O1—C6	1.379 (3)	C10—H10C	0.9800
O1—C9	1.439 (4)	C10—H10A	0.9800
O2—C7	1.371 (3)	C11—C16	1.384 (4)
O2—C10	1.438 (3)	C11—C12	1.399 (4)
O4—N1	1.232 (3)	C12—C13	1.384 (4)
O3—N1	1.221 (3)	C12—H12	0.9500
O5—C24	1.236 (3)	C13—C14	1.384 (4)
N1—C14	1.470 (4)	C13—H13	0.9500
N2—C17	1.341 (4)	C14—C15	1.373 (4)
N2—C3	1.462 (4)	C15—C16	1.394 (4)
N2—C1	1.469 (3)	C15—H15	0.9500
N19—C18A	1.304 (4)	C16—H16	0.9500
N19—C19A	1.389 (4)	C17—C18	1.357 (4)
N24A—C24	1.379 (4)	C17—H17	0.9500
N24A—C18A	1.384 (3)	C18—C18A	1.452 (4)
N24A—C25	1.467 (4)	C18—C26	1.518 (4)
C1—C8A	1.522 (4)	C19A—C20	1.403 (4)
C1—C11	1.527 (4)	C19A—C23A	1.409 (4)
C1—H1	1.0000	C20—C21	1.374 (4)
C3—C4	1.517 (4)	C20—H20	0.9500
C3—H3B	0.9900	C21—C22	1.393 (4)
C3—H3A	0.9900	C21—H21	0.9500
C4—C4A	1.510 (4)	C22—C23	1.367 (5)
C4—H4B	0.9900	C22—H22	0.9500
C4—H4A	0.9900	C23—C23A	1.401 (4)
C4A—C8A	1.388 (4)	C23—H23	0.9500
C4A—C5	1.404 (4)	C23A—C24	1.458 (4)
C5—C6	1.367 (4)	C25—C26	1.539 (4)
C5—H5	0.9500	C25—H25B	0.9900
C6—C7	1.402 (4)	C25—H25A	0.9900
C7—C8	1.383 (4)	C26—H26A	0.9900
C8—C8A	1.399 (4)	C26—H26B	0.9900
C8—H8	0.9500	C27—O6	1.418 (4)
C9—H9B	0.9800	C27—H27A	0.9800
C9—H9C	0.9800	C27—H27B	0.9800
C9—H9A	0.9800	C27—H27C	0.9800
C10—H10B	0.9800	O6—H6	0.957 (18)

C6—O1—C9	116.0 (2)	C13—C12—H12	119.7
C7—O2—C10	117.3 (2)	C11—C12—H12	119.7
O3—N1—O4	123.7 (3)	C14—C13—C12	118.4 (3)
O3—N1—C14	118.5 (3)	C14—C13—H13	120.8
O4—N1—C14	117.7 (3)	C12—C13—H13	120.8
C17—N2—C3	125.4 (2)	C15—C14—C13	122.9 (3)
C17—N2—C1	120.2 (2)	C15—C14—N1	118.3 (3)
C3—N2—C1	114.1 (2)	C13—C14—N1	118.8 (3)
C18A—N19—C19A	115.6 (2)	C14—C15—C16	117.8 (3)
C24—N24A—C18A	123.9 (3)	C14—C15—H15	121.1
C24—N24A—C25	123.0 (2)	C16—C15—H15	121.1
C18A—N24A—C25	113.1 (2)	C11—C16—C15	121.2 (3)
N2—C1—C8A	111.4 (2)	C11—C16—H16	119.4
N2—C1—C11	109.5 (2)	C15—C16—H16	119.4
C8A—C1—C11	113.0 (2)	N2—C17—C18	131.5 (3)
N2—C1—H1	107.6	N2—C17—H17	114.3
C8A—C1—H1	107.6	C18—C17—H17	114.3
C11—C1—H1	107.6	C17—C18—C18A	118.2 (3)
N2—C3—C4	108.2 (2)	C17—C18—C26	133.6 (3)
N2—C3—H3B	110.0	C18A—C18—C26	108.0 (2)
C4—C3—H3B	110.0	N19—C18A—N24A	124.4 (3)
N2—C3—H3A	110.0	N19—C18A—C18	126.9 (3)
C4—C3—H3A	110.0	N24A—C18A—C18	108.7 (3)
H3B—C3—H3A	108.4	N19—C19A—C20	117.9 (3)
C4A—C4—C3	109.9 (2)	N19—C19A—C23A	123.5 (3)
C4A—C4—H4B	109.7	C20—C19A—C23A	118.5 (3)
C3—C4—H4B	109.7	C21—C20—C19A	120.4 (3)
C4A—C4—H4A	109.7	C21—C20—H20	119.8
C3—C4—H4A	109.7	C19A—C20—H20	119.8
H4B—C4—H4A	108.2	C20—C21—C22	120.5 (3)
C8A—C4A—C5	118.8 (3)	C20—C21—H21	119.7
C8A—C4A—C4	121.3 (3)	C22—C21—H21	119.7
C5—C4A—C4	119.9 (3)	C23—C22—C21	120.3 (3)
C6—C5—C4A	121.2 (3)	C23—C22—H22	119.8
C6—C5—H5	119.4	C21—C22—H22	119.8
C4A—C5—H5	119.4	C22—C23—C23A	120.1 (3)
C5—C6—O1	124.6 (3)	C22—C23—H23	120.0
C5—C6—C7	120.3 (3)	C23A—C23—H23	120.0
O1—C6—C7	115.0 (3)	C23—C23A—C19A	120.1 (3)
O2—C7—C8	125.3 (3)	C23—C23A—C24	120.7 (3)
O2—C7—C6	115.8 (3)	C19A—C23A—C24	119.2 (3)
C8—C7—C6	118.9 (3)	O5—C24—N24A	120.5 (3)
C7—C8—C8A	121.0 (3)	O5—C24—C23A	126.3 (3)
C7—C8—H8	119.5	N24A—C24—C23A	113.2 (3)
C8A—C8—H8	119.5	N24A—C25—C26	104.1 (2)
C4A—C8A—C8	119.8 (3)	N24A—C25—H25B	110.9
C4A—C8A—C1	121.7 (3)	C26—C25—H25B	110.9
C8—C8A—C1	118.5 (3)	N24A—C25—H25A	110.9
O1—C9—H9B	109.5	C26—C25—H25A	110.9
O1—C9—H9C	109.5	H25B—C25—H25A	109.0
H9B—C9—H9C	109.5	C18—C26—C25	105.2 (2)
O1—C9—H9A	109.5	C18—C26—H26A	110.7
H9B—C9—H9A	109.5	C25—C26—H26A	110.7
H9C—C9—H9A	109.5	C18—C26—H26B	110.7
O2—C10—H10B	109.5	C25—C26—H26B	110.7
O2—C10—H10C	109.5	H26A—C26—H26B	108.8
H10B—C10—H10C	109.5	O6—C27—H27A	109.5
O2—C10—H10A	109.5	O6—C27—H27B	109.5
H10B—C10—H10A	109.5	H27A—C27—H27B	109.5
H10C—C10—H10A	109.5	O6—C27—H27C	109.5
C16—C11—C12	119.1 (3)	H27A—C27—H27C	109.5
C16—C11—C1	122.5 (3)	H27B—C27—H27C	109.5
C12—C11—C1	118.3 (3)	C27—O6—H6	109 (2)
C13—C12—C11	120.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O5	0.96	1.91	2.8581 (7)	171
C1—H1···O1ⁱ	1.00	2.55	3.4040 (8)	143
C1—H1···O2ⁱ	1.00	2.37	3.2444 (8)	146
C4—H4A···O5ⁱⁱ	0.99	2.45	3.4346 (8)	172
C9—H9B···O6ⁱⁱⁱ	0.98	2.54	3.5042 (9)	169
C15—H15···O1^iv	0.95	2.44	3.3402 (8)	159
C16—H16···O2^iv	0.95	2.59	3.3246 (8)	134
C17—H17···N19	0.95	2.47	2.8805 (7)	106
C25—H25A···O4^v	0.99	2.29	3.1224 (8)	141

Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1; (iv) −x+1/2, y+1/2, −z+3/2; (v) −x+3/2, y−1/2, −z+3/2.

Funding information

Funding for this research was provided by: the Istedod Foundation of the Republic of Uzbekistan.

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