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The crystal structure of the title compound, C18H24N2O11, a GalNAc mimic containing an α-gly­cosyl­oxy­succin­imide linkage, has been determined. The pyran­ose ring geometry is an almost perfect 4C1 chair. The torsion angle of the exocyclic hydroxy­methyl group is shown to be gauchetrans with respect to O1 and C4, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101003377/da1176sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101003377/da1176Isup2.hkl
Contains datablock I

CCDC reference: 164689

Comment top

2-Desoxy-N-acetyl-D-galactose (GalNAc) is found within the carbohydrate moiety of tumour-associated antigens such as Tn or TF, as well as in the corresponding sialylated derivatives. These carbohydrates are abundantly expressed at the surface of tumour cells and therefore represent interesting biological targets for immunological studies and for immunotherapy. Recently, several groups have devised new synthetic routes which facilitate the chemical synthesis of the glycopeptide conjugate on the basis of chemoselective oxime bond formation (Cao et al., 1995; Rodriguez et al., 1998). In this context, the title compound, (I), a mimic of GalNAc bearing an α-glycosyloxysuccinimide linkage, has been synthesized and its structure determined. \sch

The observed interatomic bond distances and angles are essentially in good agreement with those given by Allen et al. (1987), except for the distances O1—N1, O1—C1 and O5—C1, which are discussed below, and also, somewhat surprisingly, O3—C3 and O3—C13 (Table 1). If one considers the Cremer & Pople (1975) parameters, Q = 0.532 (3) Å, θ = 4.8 (3)° and ϕ2 = 210.5 (3)°, the pyranose ring has a perfect 4C1 chair conformation. This conformation is also adopted in solution, as evidenced by the large NMR coupling constant between H2 and H3 (11.8 Hz), indicating a trans diaxial arrangement.

The exocyclic hydroxymethyl group adopts a staggered gauche-trans conformation [ω = O5—C5—C6—O6 = 64.9 (3)° and C4—C5—C6—O6 = -173.2 (2)°], which has been shown by Eriksson et al. (1996) to be the preferred conformation in crystal structures having the galacto configuration, as in (I). The torsion angle ϕ (H1—C1—O1—N1) has a value of -49°, corresponding to the staggered conformer where the exoanomeric effect contributes to energy stabilization. The anomeric C1—O1 bond length of 1.449 (2) Å is greater than the average length of such bonds [1.401 (10) Å] reported by Sheldrick (1976). The O1—N1 and O5—C1 bonds also have unusually short values, of 1.373 (2) and 1.394 (3) Å, respectively, in contrast with the literature values of 1.462 Å (Walker et al., 1994) and 1.430 (10) Å (Sheldrick, 1976). Together, these data may indicate a strong endoanomeric effect, which would result in a shortening of O5—C1 and a lengthening of C1—O1.

As shown in Table 2, an intermolecular hydrogen bond contributes to the crystal packing, forming infinite chains of molecules running along the 21 axis.

Related literature top

For related literature, see: Allen et al. (1987); Cao et al. (1995); Cremer & Pople (1975); Eriksson et al. (1996); Rodriguez et al. (1998); Sheldrick (1976); Walker et al. (1994).

Experimental top

Reductive acetylation of the azide O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D– galactopyranosyl)-N-hydroxysuccinimide [prepared following the procedure of Cao et al. (1995)] under Pd/C hydrogenation in MeOH/Ac2O 9:1 provided the title compound after recrystallization from methylene chloride/diethyl ether (Rodriguez et al., 1998). Spectroscopic data: 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 6.07 (bs, 1H, 3J2,NH = 9.6 Hz, H15), 5.48 (dd, 1H, 3J4,5 = 1.3 Hz, 3J3,4 = 3.0 Hz, H4), 5.28 (d, 1H, 3J1,2 = 3.5 Hz, H1), 5.26 (m, 1H, H3), 4.95 (td, 1H, 3J5,6 or 7 = 6.1 Hz, 3J5,7 or 6 = 6.6 Hz, H5), 4.71 (ddd, 1H, 3J2,3 = 11.8 Hz, H2), 4.23 (dd, 1H, 2J6,7 = 11.5 Hz, H6 or H7), 3.91 (dd, 1H, H7 or H6), 2.71 (s, 4H, H8, H9, H10, H11), 2.13, 2.03, 2.02, 1.99 (4 s, 12H, H12, H13, H14; H16, H17, H18; H19, H20, H21; H22, H23, H24); 13C NMR (δ, p.p.m.): 170.9 (CO), 170.7 (CO), 170.6 (CO), 170.4 (CO), 170.1 (CO), 104.2 (C1), 69.2, 67.3, 67.1 (C3, C4, C5), 61.6 (C6), 47.2 (C2), 25.4 (C8, C9), 23.2 (C12), 20.7 (C14, C16, C18).

Refinement top

The y s.u. of O1 is not given, since this parameter must be fixed in space group P21. H atoms were located geometrically.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: TEXSAN (Molecular Structure Corporation, 1992-1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atom-numbering scheme and with displacement ellipsoids drawn at the 35% probability level. H atoms have been omitted for clarity.
(I) top
Crystal data top
C18H24N2O11F(000) = 468
Mr = 444.39Dx = 1.331 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 10.556 (4) ÅCell parameters from 25 reflections
b = 9.191 (1) Åθ = 20.2–26.8°
c = 12.536 (6) ŵ = 0.11 mm1
β = 114.28 (5)°T = 293 K
V = 1108.6 (7) Å3Monoclinic prism, colourless
Z = 20.38 × 0.35 × 0.34 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.009
Radiation source: X-ray tubeθmax = 30.0°, θmin = 2.1°
Graphite monochromatorh = 1414
ω scansk = 012
3547 measured reflectionsl = 017
3470 independent reflections2 standard reflections every 120 reflections
2900 reflections with I > 0.07σ(I) intensity decay: 5.5%
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.069H-atom parameters not refined
wR(F2) = 0.055Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.0002|Fo|2]
S = 1.94(Δ/σ)max = 0.030
2900 reflectionsΔρmax = 0.25 e Å3
279 parametersΔρmin = 0.19 e Å3
Crystal data top
C18H24N2O11V = 1108.6 (7) Å3
Mr = 444.39Z = 2
Monoclinic, P21Mo Kα radiation
a = 10.556 (4) ŵ = 0.11 mm1
b = 9.191 (1) ÅT = 293 K
c = 12.536 (6) Å0.38 × 0.35 × 0.34 mm
β = 114.28 (5)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.009
3547 measured reflections2 standard reflections every 120 reflections
3470 independent reflections intensity decay: 5.5%
2900 reflections with I > 0.07σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0690 restraints
wR(F2) = 0.055H-atom parameters not refined
S = 1.94Δρmax = 0.25 e Å3
2900 reflectionsΔρmin = 0.19 e Å3
279 parameters
Special details top

Refinement. The decay correction has been applied. H atoms were located by geometry.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.2804 (1)0.55250.98523 (9)0.0574 (3)
O30.1246 (1)0.6080 (1)0.72175 (9)0.0529 (3)
O40.0209 (1)0.3635 (1)0.65250 (9)0.0560 (3)
O50.2342 (1)0.3564 (1)0.85519 (8)0.0510 (3)
O60.4031 (1)0.3098 (2)0.7315 (1)0.0692 (4)
O70.5199 (2)0.5766 (3)0.9433 (2)0.1307 (7)
O80.3494 (2)0.4554 (3)1.2095 (1)0.1364 (7)
O90.0420 (2)0.3547 (1)1.0389 (1)0.0851 (4)
O100.0822 (1)0.7987 (2)0.6300 (1)0.0754 (4)
O110.1505 (2)0.4715 (2)0.4817 (1)0.0993 (5)
O120.4488 (2)0.5150 (2)0.6609 (2)0.1043 (5)
N10.4113 (2)0.5083 (2)1.0598 (1)0.0722 (4)
N20.0150 (1)0.5564 (1)0.9704 (1)0.0490 (3)
C10.1936 (2)0.4268 (2)0.9345 (1)0.0487 (4)
C20.0467 (2)0.4825 (2)0.8826 (1)0.0453 (4)
C30.0214 (2)0.5760 (2)0.7760 (1)0.0458 (4)
C40.0653 (2)0.4917 (2)0.6920 (1)0.0479 (4)
C50.2139 (2)0.4398 (2)0.7522 (1)0.0502 (4)
C60.2567 (2)0.3432 (2)0.6766 (1)0.0613 (5)
C70.5232 (2)0.5258 (3)1.0315 (2)0.1035 (8)
C80.6434 (3)0.4686 (4)1.1371 (3)0.156 (1)
C90.5863 (4)0.4200 (4)1.2241 (3)0.164 (1)
C100.4367 (3)0.4611 (3)1.1721 (2)0.1064 (7)
C110.0160 (2)0.4850 (2)1.0480 (1)0.0563 (4)
C120.0113 (3)0.5700 (2)1.1514 (2)0.0858 (6)
C130.1639 (2)0.7240 (2)0.6477 (1)0.0578 (4)
C140.3160 (2)0.7380 (3)0.5940 (2)0.0814 (6)
C150.1261 (2)0.3677 (3)0.5452 (2)0.0722 (5)
C160.2027 (3)0.2266 (3)0.5205 (2)0.1112 (8)
C170.4899 (2)0.4077 (3)0.7189 (2)0.0777 (6)
C180.6375 (2)0.3638 (4)0.7819 (2)0.1043 (8)
H10.20320.36080.99570.059*
H20.01330.40080.85700.055*
H30.07310.66360.79910.055*
H40.05490.55130.62690.058*
H50.27360.52220.77460.060*
H60.20540.25540.66260.073*
H70.23730.39130.60450.073*
H80.68420.38801.11580.190*
H90.71040.54271.17010.190*
H100.59650.31871.23650.198*
H110.63330.46971.29680.198*
H120.01300.66771.14470.105*
H130.05560.52821.22100.105*
H140.10030.56711.15350.105*
H150.02950.64520.97900.115*
H160.35600.65240.55090.099*
H170.34180.81960.54280.099*
H180.34880.75130.65350.099*
H190.14100.14970.52410.135*
H200.23910.21040.57760.135*
H210.27680.22940.44510.135*
H220.69580.43580.77150.127*
H230.65230.27340.75210.127*
H240.65880.35380.86310.127*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0593 (6)0.0465 (6)0.0500 (6)0.0088 (5)0.0061 (5)0.0044 (6)
O30.0549 (5)0.0443 (6)0.0534 (5)0.0026 (5)0.0163 (4)0.0087 (5)
O40.0584 (6)0.0501 (6)0.0474 (5)0.0068 (6)0.0096 (4)0.0073 (5)
O50.0567 (6)0.0435 (6)0.0468 (5)0.0040 (5)0.0150 (4)0.0013 (5)
O60.0630 (6)0.0717 (9)0.0715 (7)0.0117 (6)0.0261 (5)0.0094 (7)
O70.090 (1)0.188 (2)0.120 (1)0.043 (1)0.0493 (8)0.038 (1)
O80.166 (2)0.161 (2)0.0608 (8)0.034 (2)0.0249 (9)0.022 (1)
O90.155 (1)0.0272 (5)0.1010 (8)0.0100 (7)0.0808 (6)0.0012 (6)
O100.0874 (8)0.0574 (8)0.0747 (7)0.0017 (7)0.0267 (6)0.0233 (7)
O110.098 (1)0.103 (1)0.0586 (7)0.006 (1)0.0071 (7)0.0016 (8)
O120.0809 (9)0.103 (1)0.121 (1)0.0064 (9)0.0335 (8)0.0488 (9)
N10.0636 (8)0.070 (1)0.0560 (7)0.0052 (8)0.0028 (6)0.0086 (8)
N20.0730 (8)0.0255 (6)0.0500 (6)0.0002 (6)0.0268 (5)0.0014 (5)
C10.0624 (8)0.0353 (8)0.0405 (7)0.0026 (7)0.0133 (6)0.0033 (7)
C20.0572 (8)0.0297 (7)0.0454 (7)0.0078 (7)0.0174 (6)0.0004 (6)
C30.0510 (7)0.0354 (8)0.0431 (7)0.0048 (7)0.0113 (6)0.0023 (6)
C40.0521 (8)0.0452 (9)0.0417 (7)0.0047 (7)0.0145 (6)0.0023 (7)
C50.0516 (8)0.0505 (9)0.0428 (7)0.0056 (7)0.0135 (6)0.0009 (7)
C60.0613 (8)0.066 (1)0.0545 (8)0.0022 (9)0.0212 (7)0.0032 (9)
C70.065 (1)0.118 (2)0.111 (1)0.024 (1)0.020 (1)0.048 (1)
C80.070 (2)0.145 (3)0.176 (2)0.011 (2)0.027 (1)0.051 (2)
C90.129 (2)0.109 (2)0.132 (2)0.009 (2)0.068 (2)0.015 (2)
C100.127 (2)0.084 (2)0.055 (1)0.013 (2)0.016 (1)0.000 (1)
C110.081 (1)0.0288 (7)0.0647 (8)0.0099 (8)0.0361 (7)0.0070 (7)
C120.154 (2)0.045 (1)0.086 (1)0.012 (1)0.0771 (9)0.0004 (9)
C130.0785 (9)0.0475 (9)0.0432 (7)0.0152 (8)0.0207 (7)0.0082 (7)
C140.084 (1)0.083 (1)0.077 (1)0.029 (1)0.0323 (9)0.023 (1)
C150.061 (1)0.083 (1)0.0563 (9)0.002 (1)0.0072 (7)0.0239 (9)
C160.107 (2)0.089 (2)0.106 (2)0.030 (1)0.011 (1)0.039 (1)
C170.0674 (9)0.089 (1)0.079 (1)0.002 (1)0.0328 (8)0.006 (1)
C180.068 (1)0.112 (2)0.132 (2)0.015 (1)0.040 (1)0.023 (2)
Geometric parameters (Å, º) top
O1—N11.373 (2)C11—C121.496 (4)
O1—C11.449 (2)C13—C141.469 (4)
O3—C31.436 (3)C15—C161.492 (5)
O3—C131.362 (3)C17—C181.484 (4)
O4—C41.446 (3)N2—H150.83
O4—C151.347 (3)C1—H10.95
O5—C11.394 (3)C2—H20.95
O5—C51.440 (3)C3—H30.95
O6—C61.443 (3)C4—H40.95
O6—C171.339 (4)C5—H50.95
O7—C71.189 (5)C6—H60.95
O8—C101.195 (5)C6—H70.95
O9—C111.223 (3)C8—H80.95
O10—C131.192 (3)C8—H90.95
O11—C151.201 (4)C9—H100.94
O12—C171.196 (4)C9—H110.96
N1—C71.375 (5)C12—H120.95
N1—C101.390 (4)C12—H130.95
N2—C21.444 (3)C12—H140.95
N2—C111.322 (3)C14—H160.95
C1—C21.503 (3)C14—H170.95
C2—C31.518 (3)C14—H180.95
C3—C41.525 (3)C16—H190.95
C4—C51.511 (3)C16—H200.95
C5—C61.497 (4)C16—H210.95
C7—C81.502 (5)C18—H220.95
C8—C91.514 (8)C18—H230.95
C9—C101.488 (6)C18—H240.95
O3···O9i3.591 (2)O9···C2ii3.565 (3)
O4···C12ii3.571 (3)O9···C18iv3.587 (4)
O5···C12ii3.509 (4)O10···C12i3.533 (3)
O6···C10iii3.593 (4)O10···C6v3.537 (3)
O8···C14ii3.301 (4)O11···C9vi3.315 (4)
O9···N2ii2.764 (2)O12···C16v3.293 (4)
O9···C3ii3.402 (3)O12···C14vii3.575 (4)
N1—O1—C1109.9 (1)C1—C2—H2107.6
C3—O3—C13116.8 (2)C3—C2—H2107.4
C4—O4—C15117.6 (2)O3—C3—H3109.9
C1—O5—C5114.7 (2)C2—C3—H3110.0
C6—O6—C17116.8 (2)C4—C3—H3110.0
O1—N1—C7121.4 (2)O4—C4—H4109.9
O1—N1—C10120.2 (3)C3—C4—H4109.9
C7—N1—C10118.0 (3)C5—C4—H4109.9
C2—N2—C11122.2 (2)O5—C5—H5108.8
O1—C1—O5111.0 (2)C4—C5—H5108.7
O1—C1—C2105.8 (2)C6—C5—H5108.9
O5—C1—C2114.5 (2)O6—C6—H6109.0
N2—C2—C1110.6 (2)O6—C6—H7108.8
N2—C2—C3113.1 (2)C5—C6—H6109.0
C1—C2—C3110.5 (2)C5—C6—H7108.8
O3—C3—C2107.4 (2)H6—C6—H7109.7
O3—C3—C4110.4 (2)C7—C8—H8110.0
C2—C3—C4109.1 (2)C7—C8—H9110.0
O4—C4—C3108.8 (2)C9—C8—H8109.5
O4—C4—C5106.9 (2)C9—C8—H9110.2
C3—C4—C5111.3 (2)H8—C8—H9109.9
O5—C5—C4110.9 (2)C8—C9—H10111.0
O5—C5—C6106.2 (2)C8—C9—H11110.0
C4—C5—C6113.1 (2)C10—C9—H10110.6
O6—C6—C5111.5 (2)C10—C9—H11109.7
O7—C7—N1125.9 (3)H10—C9—H11109.5
O7—C7—C8130.4 (4)C11—C12—H12109.4
N1—C7—C8103.7 (4)C11—C12—H13109.4
C7—C8—C9107.2 (4)C11—C12—H14109.1
C8—C9—C10105.9 (3)H12—C12—H13109.8
O8—C10—N1123.5 (3)H12—C12—H14109.6
O8—C10—C9131.9 (4)H13—C12—H14109.4
N1—C10—C9104.5 (4)C13—C14—H16109.6
O9—C11—N2122.1 (2)C13—C14—H17109.5
O9—C11—C12121.2 (2)C13—C14—H18109.5
N2—C11—C12116.6 (2)H16—C14—H17109.4
O3—C13—O10122.4 (2)H16—C14—H18109.5
O3—C13—C14110.5 (2)H17—C14—H18109.4
O10—C13—C14127.1 (2)C15—C16—H19109.6
O4—C15—O11123.3 (3)C15—C16—H20109.3
O4—C15—C16109.7 (3)C15—C16—H21109.8
O11—C15—C16127.0 (2)H19—C16—H20109.1
O6—C17—O12122.1 (3)H19—C16—H21109.7
O6—C17—C18111.9 (3)H20—C16—H21109.3
O12—C17—C18125.9 (3)C17—C18—H22109.6
C2—N2—H15118.3C17—C18—H23109.6
C11—N2—H15118.8C17—C18—H24109.3
O1—C1—H1108.5H22—C18—H23109.5
O5—C1—H1108.5H22—C18—H24109.5
C2—C1—H1108.4H23—C18—H24109.4
N2—C2—H2107.4
O1—N1—C7—O71.1 (6)O12—C17—O6—C63.1 (4)
O1—N1—C7—C8178.1 (3)N1—O1—C1—C2164.7 (2)
O1—N1—C10—O80.4 (6)N1—C7—C8—C90.3 (5)
O1—N1—C10—C9178.7 (3)N1—C10—C9—C87.7 (5)
O1—C1—O5—C565.9 (2)N2—C2—C3—C4176.9 (2)
O1—C1—C2—N256.2 (2)C1—O1—N1—C7108.8 (3)
O1—C1—C2—C369.9 (2)C1—O1—N1—C1079.2 (3)
O3—C3—C2—N263.4 (2)C1—O5—C5—C453.9 (2)
O3—C3—C2—C1172.0 (2)C1—O5—C5—C6177.2 (2)
O3—C3—C4—O454.9 (2)C1—C2—N2—C1179.0 (2)
O3—C3—C4—C5172.5 (2)C1—C2—C3—C452.3 (2)
O4—C4—C3—C262.9 (2)C2—N2—C11—C12165.0 (2)
O4—C4—C5—O564.1 (2)C2—C1—O5—C553.7 (2)
O4—C4—C5—C655.1 (2)C2—C3—O3—C13160.5 (2)
O5—C1—O1—N170.5 (2)C2—C3—C4—C554.7 (2)
O5—C1—C2—N2178.7 (2)C3—O3—C13—C14176.7 (2)
O5—C1—C2—C352.6 (2)C3—C2—N2—C11156.4 (2)
O5—C5—C4—C354.6 (2)C3—C4—O4—C15101.4 (2)
O5—C5—C6—O664.9 (3)C3—C4—C5—C6173.9 (2)
O6—C6—C5—C4173.2 (2)C4—O4—C15—C16179.9 (2)
O7—C7—N1—C10173.2 (4)C4—C3—O3—C1380.6 (2)
O7—C7—C8—C9178.9 (5)C5—C4—O4—C15138.3 (2)
O8—C10—N1—C7172.7 (4)C5—C6—O6—C1783.7 (3)
O8—C10—C9—C8174.2 (5)C6—O6—C17—C18178.2 (3)
O9—C11—N2—C212.2 (4)C7—N1—C10—C99.0 (4)
O10—C13—O3—C31.8 (3)C7—C8—C9—C104.7 (5)
O11—C15—O4—C40.5 (4)C8—C7—N1—C106.0 (4)
Symmetry codes: (i) x, y1/2, z2; (ii) x, y+1/2, z2; (iii) x1, y+1/2, z2; (iv) x+1, y, z; (v) x, y1/2, z1; (vi) x+1, y, z+1; (vii) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H15···O9i0.831.952.764 (2)167
Symmetry code: (i) x, y1/2, z2.

Experimental details

Crystal data
Chemical formulaC18H24N2O11
Mr444.39
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)10.556 (4), 9.191 (1), 12.536 (6)
β (°) 114.28 (5)
V3)1108.6 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.38 × 0.35 × 0.34
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 0.07σ(I)] reflections
3547, 3470, 2900
Rint0.009
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.069, 0.055, 1.94
No. of reflections2900
No. of parameters279
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.25, 0.19

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, TEXSAN (Molecular Structure Corporation, 1992-1997), SIR92 (Altomare et al., 1993), TEXSAN, ORTEPII (Johnson, 1976).

Selected geometric parameters (Å, º) top
O1—N11.373 (2)N1—C71.375 (5)
O1—C11.449 (2)N1—C101.390 (4)
O3—C31.436 (3)N2—C21.444 (3)
O3—C131.362 (3)N2—C111.322 (3)
O4—C41.446 (3)C1—C21.503 (3)
O4—C151.347 (3)C2—C31.518 (3)
O5—C11.394 (3)C3—C41.525 (3)
O5—C51.440 (3)C4—C51.511 (3)
O6—C61.443 (3)C5—C61.497 (4)
O6—C171.339 (4)
N1—O1—C1109.9 (1)N2—C2—C3113.1 (2)
C3—O3—C13116.8 (2)C1—C2—C3110.5 (2)
C4—O4—C15117.6 (2)O3—C3—C2107.4 (2)
C1—O5—C5114.7 (2)O3—C3—C4110.4 (2)
C6—O6—C17116.8 (2)C2—C3—C4109.1 (2)
O1—N1—C7121.4 (2)O4—C4—C3108.8 (2)
O1—N1—C10120.2 (3)O4—C4—C5106.9 (2)
C7—N1—C10118.0 (3)C3—C4—C5111.3 (2)
C2—N2—C11122.2 (2)O5—C5—C4110.9 (2)
O1—C1—O5111.0 (2)O5—C5—C6106.2 (2)
O1—C1—C2105.8 (2)C4—C5—C6113.1 (2)
O5—C1—C2114.5 (2)O6—C6—C5111.5 (2)
N2—C2—C1110.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H15···O9i0.831.952.764 (2)167.2
Symmetry code: (i) x, y1/2, z2.
 

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