Crystal structure of 3-O-benzyl-4(R)-C-(1-benzyl-1H-1,2,3-triazol-4-yl)-1,2-O-iso­propyl­idene-α-d-erythro­furan­ose

Semjonovs, N.; Rjabovs, V.; Stepanovs, D.; Turks, M.

doi:10.1107/S2056989015022434

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ISSN: 2056-9890

Volume 71| Part 12| December 2015| Pages 1542-1544

https://doi.org/10.1107/S2056989015022434

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Crystal structure of 3-O-benzyl-4(R)-C-(1-benzyl-1H-1,2,3-triazol-4-yl)-1,2-O-isopropylidene-α-D-erythrofuranose

Nikita Semjonovs,^a Vitalijs Rjabovs,^a Dmitrijs Stepanovs ^b and Maris Turks ^a ^*

^aInstitute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena 3/7, Riga, LV-1048, Latvia, and ^bLatvian Institute of Organic Synthesis, Str. Aizkraukles 21, Riga, LV 1006, Latvia
^*Correspondence e-mail: d_stepanovs@osi.lv, maris_turks@ktf.rtu.lv

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 15 November 2015; accepted 24 November 2015; online 28 November 2015)

The title compound, C₂₃H₂₅N₃O₄, {systematic name: 1-benzyl-4-[(3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1H-1,2,3-triazole}, consists of a substituted 2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole. The furanose ring adopts an envelope conformation close to C₃-exo, where the C atom substituted by the benzyloxy group is the flap. The fused dioxolane ring also adopts an envelope conformation, with the methylene C atom as the flap. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming zigzag chains along [010].

Keywords: crystal structure; 1,2,3-triazole; click chemistry; carbohydrate triazole conjugate; pseudo-nucleoside.

CCDC reference: 1438541

1. Chemical context

The title compound, (1), was obtained in a one-pot multicomponent click reaction (Rostovtsev et al., 2002 ; Kumar et al., 2009 ) of alkyne (2), sodium azide, and benzyl bromide (3), in the presence of copper(II) sulfate and sodium ascorbate in THF solution at 323 K (Fig. 1). Similar C(4)-linked carbohydrate-1,2,3-triazole conjugates have been synthesized under different reaction conditions (Dururgkar et al., 2009 ; Kaliappan et al., 2009 ; Strakova et al., 2011 ). Many carbohydrate-triazole conjugates have been probed as glycosidase inhibitors (Rjabova et al., 2012 ), galectin inhibitors (Mackeviča et al., 2014 ), and antimicrobial agents (Jana et al., 2014 ; Reddy et al., 2014 ). Starting alkyne (2) and similar carbohydrate alkynes have been studied previously as precursors for triazole syntheses (Ciunik & Jarosz, 1998 ; Jarosz, 1988 ; Rjabovs et al., 2015 ; Strakova et al., 2011).

Figure 1
Synthesis of the title compound (1).

2. Structural commentary

The title compound, Fig. 2, consists of a tetrahydrofuran core fused with a dioxolane ring, and substituted with benzyl and (1-benzyl)-1H-1,2,3-triazol-4-yl moieties. The furanose ring adopts an envelope conformation close to C₃-exo, where atom C3 deviates from the mean plane through atoms O1/C1/C2/C4 by 0.577 (4) Å. The fused dioxolane ring also adopts an envelope conformation, where atom C2 deviates from the mean plane through the four near planar atoms (O17/C18/O19/C1) by 0.364 (4) Å. The dihedral angle between the mean planes of the fragments of these rings is 69.3 (1)°.

Figure 2
The molecular structure of compound (1), showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

3. Supramolecular features

In the crystal, weak C—H⋯O hydrogen bonds (Table 1) link the molecules, forming zigzag chains along the b-axis direction. There are no other significant intermolecular interactions present.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21C⋯O19ⁱ	0.96	2.53	3.285 (3)	136
Symmetry code: (i) $[-x+3, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

4. Database survey

A search of the Cambridge Structural Database (Version 5.36; Groom & Allen, 2014 ) for substituted 3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxoles gave 485 hits (excluding organometallics). Three of them are triazoles: (4R)-4-(2-allyl-2H-1,2,3-triazol-4-yl)-1,2-O-isopropylidene-L-threose (LOHTIM; Jenkinson et al., 2008 ) and 5-({5-[6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1H-1,2,3-triazol-1-yl}methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (DOPVAH01 and DOPVEL01, two stereoisomers; Kayet et al., 2014 ).

5. Synthesis and crystallization

The synthesis of the title compound is illustrated in Fig. 1. Sodium azide (98 mg, 1.5 mmol, 3 eq.) was added to a solution of alkyne (2) (140 mg, 0.5 mmol, 1 eq.) in THF (10 ml). The mixture was cooled to 273 K and benzyl bromide (3) (70 µl, 0.6 mmol, 1.2 eq.) was added. After 20 min solutions of copper(II) sulfate pentahydrate (12 mg, 10 mol%) in water (0.5 ml) and sodium ascorbate (20 mg, 20 mol%) in water (0.5 ml) were added and the resulting reaction mixture was warmed to 323 K. After 3 h the solvent was evaporated under reduced pressure, the residue was dissolved in EtOAc (20 ml). The organic layer was washed with a saturated aqueous solution of NaHCO₃ (3 × 5 ml) and brine (3 × 5 ml), dried over Na₂SO₄, filtered and evaporated. The solid residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc giving a white crystalline solid (yield: 132 mg, 65%; m.p. 430-431 K). Colourless plate-like crystals were obtained by slow evaporation of a dichloromethane solution at ambient temperature.

Spectroscopic data: IR (KBr, cm⁻¹): 3125, 3085, 2985, 2895, 1495, 1455, 1385, 1370, 1230, 1145, 1100, 1075, 1040, 995. ¹H NMR (CDCl₃, 300 MHz): δ 7.37 (m, 4H), 7.28–7.16 (m, 6H), 5.83 (d, J = 3.6 Hz, 1H), 5.54 (d, AB syst., J = 14.8 Hz, 1H), 5.47 (d, AB syst., J = 14.8 Hz, 1H), 5.13 (d, J = 9.0 Hz, 1H), 4.64 (m, 2H), 4.55 (d, AB syst., J = 12.2 Hz, 1H), 4.25 (dd, J = 8.0, 4.0 Hz, 1H), 1.63 (s, 3H), 1.37 (s, 3H). ¹³C NMR (CDCl₃, 75 MHz): ¹³C NMR (75 MHz, CDCl₃) δ 145.12, 137.64, 134.54, 129.28, 128.96, 128.43, 128.27, 128.12, 127.98, 123.26, 113.14, 103.98, 81.43, 77.93, 72.59, 72.57, 54.31, 26.92, 26.54.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The C-bound H atoms were positioned geometrically and refined as riding on their parent atoms: C—H = 0.93–0.98Å with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for other H atoms. Reflection (0,0,2) whose intensity was affected by the beam-stop was removed from the final refinement. In the final cycles of refinement, in the absence of significant anomalous scattering effects, Friedel pairs were merged and Δf′′ set to zero.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₃H₂₅N₃O₄
M_r	407.46
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	9.5276 (2), 10.0030 (2), 21.9495 (7)
V (Å³)	2091.89 (9)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.31 × 0.17 × 0.12

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5878, 3423, 1983
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.106, 1.02
No. of reflections	3423
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20
Computer programs: KappaCCD Server Software (Nonius, 1997 ), DENZO and SCALEPACK (Otwinowski & Minor, 1997 ), SIR2011 (Burla et al., 2012 ), ORTEP-3 for Windows (Farrugia, 2012 ), SHELXL97 (Sheldrick, 2008 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1438541

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989015022434/su5245sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015022434/su5245Isup2.hkl

checkCIF report

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2011 (Burla et al., 2012); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

3-O-Benzyl-4(R)-C-(1-benzyl-1H-1,2,3-triazol-4-yl)-1,2-O-isopropylidene-α-D-erythrofuranose top

Crystal data top

C₂₃H₂₅N₃O₄	D_x = 1.294 Mg m⁻³
M_r = 407.46	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 11742 reflections
a = 9.5276 (2) Å	θ = 1.0–30.0°
b = 10.0030 (2) Å	µ = 0.09 mm⁻¹
c = 21.9495 (7) Å	T = 173 K
V = 2091.89 (9) Å³	Plate, colourless
Z = 4	0.31 × 0.17 × 0.12 mm
F(000) = 864

Data collection top

Nonius KappaCCD diffractometer	1983 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.070
Graphite monochromator	θ_max = 30.1°, θ_min = 2.2°
φ and ω scan	h = −13→13
5878 measured reflections	k = −14→14
3423 independent reflections	l = −30→30

Refinement top

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0425P)²] where P = (F_o² + 2F_c²)/3
3423 reflections	(Δ/σ)_max < 0.001
273 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	1.16295 (19)	0.88874 (17)	0.19794 (8)	0.0303 (4)
C1	1.2698 (3)	0.9325 (2)	0.23846 (11)	0.0257 (6)
H1	1.2802	1.0299	0.2367	0.031*
C2	1.2262 (3)	0.8879 (2)	0.30203 (12)	0.0264 (6)
H2	1.2484	0.9535	0.3338	0.032*
C3	1.0704 (3)	0.8622 (2)	0.29521 (11)	0.0249 (6)
H3	1.0190	0.9468	0.2983	0.030*
C4	1.0612 (3)	0.8090 (2)	0.23003 (11)	0.0255 (6)
H4	1.0914	0.7153	0.2295	0.031*
C5	0.9254 (3)	0.8207 (2)	0.19804 (11)	0.0247 (6)
C6	0.8620 (3)	0.9299 (3)	0.17250 (11)	0.0281 (7)
H6	0.8943	1.0176	0.1724	0.034*
N7	0.8440 (3)	0.7120 (2)	0.18755 (10)	0.0330 (6)
N8	0.7314 (3)	0.7502 (2)	0.15626 (10)	0.0340 (6)
N9	0.7435 (2)	0.8834 (2)	0.14768 (9)	0.0281 (5)
C10	0.6401 (3)	0.9530 (3)	0.11021 (12)	0.0347 (7)
H10A	0.6524	1.0487	0.1150	0.042*
H10B	0.5466	0.9304	0.1243	0.042*
C11	0.6530 (3)	0.9172 (2)	0.04351 (12)	0.0278 (6)
C12	0.7666 (4)	0.9615 (3)	0.00985 (13)	0.0424 (8)
H12	0.8340	1.0160	0.0278	0.051*
C13	0.7797 (4)	0.9242 (3)	−0.05091 (14)	0.0509 (9)
H13	0.8563	0.9536	−0.0735	0.061*
C14	0.6808 (4)	0.8446 (3)	−0.07767 (14)	0.0507 (9)
H14	0.6908	0.8191	−0.1182	0.061*
C15	0.5672 (4)	0.8026 (3)	−0.04496 (15)	0.0511 (9)
H15	0.4987	0.7502	−0.0635	0.061*
C16	0.5537 (3)	0.8380 (3)	0.01595 (14)	0.0402 (8)
H16	0.4770	0.8078	0.0382	0.048*
O17	1.29867 (19)	0.76405 (16)	0.30941 (8)	0.0286 (5)
C18	1.4170 (3)	0.7600 (2)	0.26879 (11)	0.0278 (6)
O19	1.3983 (2)	0.86916 (16)	0.22727 (8)	0.0308 (5)
C20	1.5517 (3)	0.7802 (3)	0.30359 (13)	0.0360 (7)
H20A	1.5477	0.8636	0.3252	0.054*
H20B	1.6292	0.7816	0.2757	0.054*
H20C	1.5639	0.7084	0.3321	0.054*
C21	1.4123 (3)	0.6299 (2)	0.23368 (12)	0.0364 (7)
H21A	1.4858	0.6291	0.2038	0.055*
H21B	1.3230	0.6216	0.2137	0.055*
H21C	1.4250	0.5564	0.2613	0.055*
O3'	1.0121 (2)	0.76803 (16)	0.33605 (8)	0.0283 (4)
C4'	0.9967 (4)	0.8185 (3)	0.39562 (13)	0.0497 (9)
H4'1	0.9405	0.8992	0.3945	0.060*
H4'2	1.0883	0.8413	0.4119	0.060*
C5'	0.9281 (3)	0.7180 (2)	0.43610 (12)	0.0303 (7)
C6'	0.9439 (4)	0.7281 (3)	0.49853 (14)	0.0446 (8)
H6'	0.9965	0.7976	0.5150	0.054*
C7'	0.8820 (4)	0.6357 (3)	0.53642 (13)	0.0495 (9)
H7'	0.8924	0.6437	0.5784	0.059*
C8'	0.8054 (4)	0.5322 (3)	0.51301 (15)	0.0500 (9)
H8'	0.7648	0.4692	0.5388	0.060*
C9'	0.7889 (4)	0.5223 (3)	0.45101 (15)	0.0480 (9)
H9'	0.7360	0.4528	0.4348	0.058*
C10'	0.8498 (3)	0.6139 (3)	0.41277 (12)	0.0360 (7)
H10'	0.8383	0.6058	0.3709	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0293 (11)	0.0383 (10)	0.0232 (9)	−0.0053 (9)	−0.0004 (9)	0.0065 (8)
C1	0.0310 (17)	0.0218 (14)	0.0244 (14)	−0.0016 (13)	0.0007 (13)	0.0025 (11)
C2	0.0315 (16)	0.0208 (13)	0.0267 (14)	0.0026 (12)	−0.0007 (13)	−0.0005 (11)
C3	0.0319 (16)	0.0216 (12)	0.0211 (13)	0.0002 (13)	0.0030 (13)	−0.0002 (10)
C4	0.0318 (17)	0.0212 (13)	0.0235 (13)	0.0007 (13)	0.0046 (13)	0.0038 (10)
C5	0.0325 (16)	0.0231 (12)	0.0185 (13)	−0.0036 (13)	0.0028 (13)	0.0020 (11)
C6	0.0304 (17)	0.0298 (14)	0.0242 (14)	−0.0049 (13)	−0.0024 (13)	−0.0029 (11)
N7	0.0321 (14)	0.0315 (13)	0.0354 (14)	−0.0074 (12)	−0.0046 (12)	0.0026 (10)
N8	0.0346 (14)	0.0320 (13)	0.0354 (13)	−0.0103 (12)	0.0012 (12)	0.0013 (11)
N9	0.0278 (14)	0.0283 (13)	0.0281 (12)	0.0003 (11)	−0.0023 (11)	−0.0025 (10)
C10	0.0305 (17)	0.0389 (15)	0.0347 (16)	0.0069 (15)	−0.0020 (14)	−0.0042 (13)
C11	0.0285 (16)	0.0281 (14)	0.0268 (14)	0.0061 (13)	−0.0068 (13)	−0.0018 (12)
C12	0.042 (2)	0.0478 (19)	0.0371 (18)	−0.0066 (17)	−0.0070 (16)	−0.0003 (14)
C13	0.053 (2)	0.061 (2)	0.0384 (19)	0.0017 (19)	0.0041 (18)	0.0066 (17)
C14	0.071 (3)	0.053 (2)	0.0280 (17)	0.0107 (19)	−0.0061 (19)	−0.0054 (15)
C15	0.061 (3)	0.0497 (18)	0.043 (2)	−0.0042 (19)	−0.016 (2)	−0.0110 (15)
C16	0.0359 (19)	0.0394 (17)	0.0452 (19)	−0.0010 (15)	−0.0034 (17)	−0.0013 (14)
O17	0.0303 (11)	0.0232 (9)	0.0324 (10)	0.0064 (8)	0.0054 (9)	0.0073 (8)
C18	0.0317 (16)	0.0252 (13)	0.0266 (14)	0.0049 (13)	0.0040 (13)	0.0039 (11)
O19	0.0279 (11)	0.0299 (9)	0.0346 (10)	0.0030 (9)	0.0061 (9)	0.0087 (8)
C20	0.0371 (18)	0.0359 (16)	0.0350 (16)	0.0024 (14)	−0.0021 (15)	0.0045 (13)
C21	0.0406 (19)	0.0271 (14)	0.0415 (17)	0.0033 (15)	0.0032 (16)	−0.0038 (12)
O3'	0.0390 (11)	0.0255 (9)	0.0203 (9)	−0.0023 (9)	0.0070 (8)	0.0003 (8)
C4'	0.080 (3)	0.0394 (17)	0.0298 (17)	−0.0144 (19)	0.0176 (18)	−0.0088 (13)
C5'	0.0356 (18)	0.0296 (14)	0.0258 (15)	−0.0002 (14)	0.0070 (13)	−0.0038 (11)
C6'	0.050 (2)	0.0518 (19)	0.0317 (17)	−0.0111 (18)	0.0060 (16)	−0.0077 (14)
C7'	0.060 (2)	0.064 (2)	0.0240 (16)	−0.003 (2)	0.0109 (17)	0.0030 (15)
C8'	0.061 (3)	0.0463 (19)	0.043 (2)	−0.0046 (18)	0.0200 (18)	0.0107 (15)
C9'	0.053 (2)	0.0410 (17)	0.050 (2)	−0.0119 (17)	0.0146 (19)	−0.0063 (16)
C10'	0.0406 (18)	0.0404 (17)	0.0270 (15)	−0.0024 (16)	0.0031 (14)	−0.0011 (13)

Geometric parameters (Å, º) top

O1—C1	1.421 (3)	C14—H14	0.9300
O1—C4	1.439 (3)	C15—C16	1.389 (4)
C1—O19	1.400 (3)	C15—H15	0.9300
C1—C2	1.523 (3)	C16—H16	0.9300
C1—H1	0.9800	O17—C18	1.438 (3)
C2—O17	1.428 (3)	C18—O19	1.433 (3)
C2—C3	1.514 (4)	C18—C20	1.507 (4)
C2—H2	0.9800	C18—C21	1.513 (3)
C3—O3'	1.414 (3)	C20—H20A	0.9600
C3—C4	1.529 (3)	C20—H20B	0.9600
C3—H3	0.9800	C20—H20C	0.9600
C4—C5	1.477 (4)	C21—H21A	0.9600
C4—H4	0.9800	C21—H21B	0.9600
C5—N7	1.355 (3)	C21—H21C	0.9600
C5—C6	1.369 (3)	O3'—C4'	1.409 (3)
C6—N9	1.337 (3)	C4'—C5'	1.492 (4)
C6—H6	0.9300	C4'—H4'1	0.9700
N7—N8	1.330 (3)	C4'—H4'2	0.9700
N8—N9	1.351 (3)	C5'—C10'	1.379 (4)
N9—C10	1.460 (3)	C5'—C6'	1.382 (4)
C10—C11	1.513 (3)	C6'—C7'	1.376 (4)
C10—H10A	0.9700	C6'—H6'	0.9300
C10—H10B	0.9700	C7'—C8'	1.367 (4)
C11—C16	1.374 (4)	C7'—H7'	0.9300
C11—C12	1.383 (4)	C8'—C9'	1.373 (4)
C12—C13	1.391 (4)	C8'—H8'	0.9300
C12—H12	0.9300	C9'—C10'	1.371 (4)
C13—C14	1.366 (4)	C9'—H9'	0.9300
C13—H13	0.9300	C10'—H10'	0.9300
C14—C15	1.365 (5)

C1—O1—C4	110.29 (18)	C13—C14—H14	120.0
O19—C1—O1	112.16 (19)	C14—C15—C16	120.0 (3)
O19—C1—C2	105.47 (19)	C14—C15—H15	120.0
O1—C1—C2	106.7 (2)	C16—C15—H15	120.0
O19—C1—H1	110.8	C11—C16—C15	120.5 (3)
O1—C1—H1	110.8	C11—C16—H16	119.8
C2—C1—H1	110.8	C15—C16—H16	119.8
O17—C2—C3	109.7 (2)	C2—O17—C18	109.46 (17)
O17—C2—C1	103.1 (2)	O19—C18—O17	105.97 (19)
C3—C2—C1	103.1 (2)	O19—C18—C20	109.0 (2)
O17—C2—H2	113.3	O17—C18—C20	110.5 (2)
C3—C2—H2	113.3	O19—C18—C21	109.1 (2)
C1—C2—H2	113.3	O17—C18—C21	108.4 (2)
O3'—C3—C2	115.8 (2)	C20—C18—C21	113.5 (2)
O3'—C3—C4	109.82 (19)	C1—O19—C18	110.00 (19)
C2—C3—C4	102.0 (2)	C18—C20—H20A	109.5
O3'—C3—H3	109.6	C18—C20—H20B	109.5
C2—C3—H3	109.6	H20A—C20—H20B	109.5
C4—C3—H3	109.6	C18—C20—H20C	109.5
O1—C4—C5	108.25 (19)	H20A—C20—H20C	109.5
O1—C4—C3	103.10 (19)	H20B—C20—H20C	109.5
C5—C4—C3	117.9 (2)	C18—C21—H21A	109.5
O1—C4—H4	109.1	C18—C21—H21B	109.5
C5—C4—H4	109.1	H21A—C21—H21B	109.5
C3—C4—H4	109.1	C18—C21—H21C	109.5
N7—C5—C6	108.5 (2)	H21A—C21—H21C	109.5
N7—C5—C4	121.3 (2)	H21B—C21—H21C	109.5
C6—C5—C4	130.2 (2)	C4'—O3'—C3	113.00 (19)
N9—C6—C5	105.2 (2)	O3'—C4'—C5'	110.9 (2)
N9—C6—H6	127.4	O3'—C4'—H4'1	109.5
C5—C6—H6	127.4	C5'—C4'—H4'1	109.5
N8—N7—C5	108.6 (2)	O3'—C4'—H4'2	109.5
N7—N8—N9	106.6 (2)	C5'—C4'—H4'2	109.5
C6—N9—N8	111.0 (2)	H4'1—C4'—H4'2	108.0
C6—N9—C10	129.3 (2)	C10'—C5'—C6'	118.8 (3)
N8—N9—C10	119.5 (2)	C10'—C5'—C4'	121.6 (2)
N9—C10—C11	112.1 (2)	C6'—C5'—C4'	119.5 (3)
N9—C10—H10A	109.2	C7'—C6'—C5'	120.2 (3)
C11—C10—H10A	109.2	C7'—C6'—H6'	119.9
N9—C10—H10B	109.2	C5'—C6'—H6'	119.9
C11—C10—H10B	109.2	C8'—C7'—C6'	120.7 (3)
H10A—C10—H10B	107.9	C8'—C7'—H7'	119.7
C16—C11—C12	119.2 (3)	C6'—C7'—H7'	119.7
C16—C11—C10	120.5 (3)	C7'—C8'—C9'	119.2 (3)
C12—C11—C10	120.3 (3)	C7'—C8'—H8'	120.4
C11—C12—C13	119.8 (3)	C9'—C8'—H8'	120.4
C11—C12—H12	120.1	C10'—C9'—C8'	120.7 (3)
C13—C12—H12	120.1	C10'—C9'—H9'	119.7
C14—C13—C12	120.4 (3)	C8'—C9'—H9'	119.7
C14—C13—H13	119.8	C9'—C10'—C5'	120.4 (3)
C12—C13—H13	119.8	C9'—C10'—H10'	119.8
C15—C14—C13	120.0 (3)	C5'—C10'—H10'	119.8
C15—C14—H14	120.0

C4—O1—C1—O19	109.7 (2)	N9—C10—C11—C12	−70.7 (3)
C4—O1—C1—C2	−5.3 (3)	C16—C11—C12—C13	−0.8 (4)
O19—C1—C2—O17	−24.2 (2)	C10—C11—C12—C13	177.9 (3)
O1—C1—C2—O17	95.2 (2)	C11—C12—C13—C14	0.3 (5)
O19—C1—C2—C3	−138.4 (2)	C12—C13—C14—C15	0.8 (5)
O1—C1—C2—C3	−19.0 (3)	C13—C14—C15—C16	−1.6 (5)
O17—C2—C3—O3'	44.2 (3)	C12—C11—C16—C15	0.1 (4)
C1—C2—C3—O3'	153.50 (19)	C10—C11—C16—C15	−178.6 (3)
O17—C2—C3—C4	−75.0 (2)	C14—C15—C16—C11	1.1 (5)
C1—C2—C3—C4	34.3 (2)	C3—C2—O17—C18	131.7 (2)
C1—O1—C4—C5	152.8 (2)	C1—C2—O17—C18	22.4 (2)
C1—O1—C4—C3	27.2 (3)	C2—O17—C18—O19	−12.5 (2)
O3'—C3—C4—O1	−161.15 (19)	C2—O17—C18—C20	105.5 (2)
C2—C3—C4—O1	−37.8 (2)	C2—O17—C18—C21	−129.5 (2)
O3'—C3—C4—C5	79.7 (3)	O1—C1—O19—C18	−98.2 (2)
C2—C3—C4—C5	−156.9 (2)	C2—C1—O19—C18	17.6 (3)
O1—C4—C5—N7	136.0 (2)	O17—C18—O19—C1	−4.0 (3)
C3—C4—C5—N7	−107.6 (3)	C20—C18—O19—C1	−123.0 (2)
O1—C4—C5—C6	−41.0 (4)	C21—C18—O19—C1	112.5 (2)
C3—C4—C5—C6	75.3 (3)	C2—C3—O3'—C4'	74.5 (3)
N7—C5—C6—N9	0.4 (3)	C4—C3—O3'—C4'	−170.7 (3)
C4—C5—C6—N9	177.7 (2)	C3—O3'—C4'—C5'	177.0 (2)
C6—C5—N7—N8	−0.1 (3)	O3'—C4'—C5'—C10'	−20.4 (4)
C4—C5—N7—N8	−177.7 (2)	O3'—C4'—C5'—C6'	159.0 (3)
C5—N7—N8—N9	−0.3 (3)	C10'—C5'—C6'—C7'	−0.2 (5)
C5—C6—N9—N8	−0.5 (3)	C4'—C5'—C6'—C7'	−179.6 (3)
C5—C6—N9—C10	−174.5 (2)	C5'—C6'—C7'—C8'	0.6 (5)
N7—N8—N9—C6	0.5 (3)	C6'—C7'—C8'—C9'	−0.9 (5)
N7—N8—N9—C10	175.2 (2)	C7'—C8'—C9'—C10'	0.8 (5)
C6—N9—C10—C11	103.7 (3)	C8'—C9'—C10'—C5'	−0.3 (5)
N8—N9—C10—C11	−69.9 (3)	C6'—C5'—C10'—C9'	0.0 (5)
N9—C10—C11—C16	108.0 (3)	C4'—C5'—C10'—C9'	179.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21C···O19ⁱ	0.96	2.53	3.285 (3)	136

Symmetry code: (i) −x+3, y−1/2, −z+1/2.

Acknowledgements

JSC `Olainfarm' is acknowledged for the donation of diacetone-D-glucose and JSC `Grindeks' is acknowledged for the donation of organic solvents.

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