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The title compound, C31H32N2O7·0.25C4H8O2, is a key inter­mediate in the synthesis of [18F]fluorine-labelled thymidine (18F-FLT), which is the most widely used mol­ecular imaging probe for positron emission tomography (PET). The crystallographic asymmetric unit contains two independent thymine mol­ecules plus one partially occupied site for an ethyl acetate molecule. The two independent thymine mol­ecules show similar geometrical features, except that the dimeth­oxy­trityl groups adopt different orientations with respect to the remainder of the mol­ecule. Each thymine base adopts an anti conformation with respect to the attached de­oxy­ribose ring, and the de­oxy­ribose rings show C3-endo puckering. The conformation of the side chain at the C1 position of the de­oxy­ribose ring is gauche+. Inter­molecular N—H...O and O—H...O hydrogen bonds link the mol­ecules into one-dimensional chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827011204351X/bi3048sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827011204351X/bi3048Isup2.hkl
Contains datablock I

CCDC reference: 914660

Comment top

[18F]Fluorine-labeled thymidine (FLT) appears to be the most promising radiopharmaceutical because of its lack of in vivo degradation, metabolic trapping in proliferating cells, and the favorable half life for PET imaging (Troost et al., 2010; Agool et al., 2011). The title compound, (I), is one of the key intermediates in the chemical synthesis of 18F-FLT. It comprises thymidine protected at the 5'-O-position by reaction with dimethoxytrityl chloride in pyridine (Martin et al., 2002; Yun et al., 2003).

The crystal structure of (I) has two independent molecules in the asymmetric unit (molecules A and B; Fig. 1) and one ethyl acetate molecule with a site-occupancy factor of 0.50. The bond lengths and angles (Table 1) are similar to those reported for other deoxythymidine analogs (Young & Wilson, 1975; Sato, 1988; Jia et al., 1990a,b). The two molecules exhibit similar geometrical features, except that the dimethoxytrityl group adopts a different orientation with respect to the remainder of the molecule (Fig. 2). The conformation of the thymine ring with respect to the deoxyribose ring is anti, as inferred from the torsion angles about the glycosyl bond (C8—N1—C4—O1). The thymine ring (O3/O4/N1/N2/C5–C9) is essentially planar (average deviations from the mean plane of 0.019 and 0.015 Å for molecules A and B, respectively), and makes dihedral angles of 81.3 (1) and 80.1 (1)° with the mean plane through the attached deoxyribose ring (O1/C1–C4).

The C—C bonds within the deoxyribose rings (Table 1) have bond lengths in the range 1.514 (5)–1.543 (5) Å. The conformations of the rings are C3-endo, with atoms C3 and C3' displaced by 0.52 and 0.51 Å, respectively, from the mean plane constituted by the remaining four atoms of each deoxyribose ring. The puckering mode is described by the pseudorotation phase angle, P (Altona & Sundaralingam, 1972; Saenger, 1984). Here, P = 164.5 (3) and 158.2 (3)° for molecules A and B, respectively. The ring puckering amplitude τm= 34.7 (2) and 34.0 (2)°, which is in agreement with (τm) = 38±3° observed for nucleosides. Further insight into the distortions is obtained from the Cremer–Pople puckering parameters (Cremer & Pople, 1975): for molecule A, Q = 0.334 (4) Å and Φ = 76.1 (6)°; for molecule B, Q = 0.326 (4) Å and Φ = 70.3 (6)°.

The conformation about the C1—C10 and C1'—C10' bonds is gauche+ (g+), as seen from their torsion angles (Table 1). Although the g+ conformation is the most common for the side chain at C1 for cytidine and 2'-deoxycytidine nucleosides (Young & Wilson, 1975; Jia et al., 1990a; Audette et al., 1997, 1998), some 2'-deoxycytidine analogues display the trans conformation (Sato, 1988; Jia et al., 1990b; Napper et al., 1995). The torsion angles about the O5—C10 and O5'—C10' bonds (Table 1) show that the dimethoxytrityl group is in a staggered orientation, as in other trityl nucleoside structures (Capron et al., 1994). As shown in Fig. 2, the dimethyloxytrityl groups adopt different orientations in molecules A and B, related by rotation of the group around the C11—O5 or C11'—O5' bonds.

In the crystal structure, molecules A and B are linked into one-dimensional chains running parallel to the a axis by several intermolecular hydrogen bonds (Table 2 and Fig. 3). The thymine rings make an approximately centrosymmetric interaction through pairs of N2'—H2'N···O4 and N2—H2N···O4' hydrogen bonds. Neighbouring pairs of molecules are then linked by O—H···O hydrogen bonds from the exocyclic hydroxy group of the deoxyfuranose ring to the O atoms of the thymine groups. These interactions are bifurcated, viz. O2—H2O···O3i and O2'—H2'O···O3'ii, and O2—H2O···O4'i and O2'—H2'O···O4ii (symmetry codes are as in Table 2).

Related literature top

For related literature, see: Agool et al. (2011); Altona & Sundaralingam (1972); Audette et al. (1997, 1998); Capron et al. (1994); Cremer & Pople (1975); Jia et al. (1990a, 1990b); Martin et al. (2002); Napper et al. (1995); Saenger (1984); Sato (1988); Troost et al. (2010); Young & Wilson (1975); Yun et al. (2003).

Experimental top

The title compound was synthesized according to the literature procedure of Yun et al. (2003). The crude product was recrystallized from ethyl acetate (m.p. 349.8–350.3 K, literature 350 K). 1H NMR (400 MHz; DMSO-d6): δ 7.29–6.84 (m, 14H, Ar—H and H-6), 3.85 (m, 1H, H-4'), 3.73 (s, 6H, OCH3), 3.42 (m, 2H, H-5), 2.51 (m, 2H, H-2), 1.79 (s, 3H, 5-CH3). 13C NMR (100 MHz, DMSO-d6): δ 85.2 (C-1'), 83.7 (CPh3), 80.3 (C-4'), 69.0 (C-3'), 60.1 (C-5'), 55.3 (OCH3), 41.4 (C-2'), 12.8 (CH3).

Refinement top

H atoms bound to C atoms were placed geometrically and refined using a riding model, with C—H = 0.95–1.00 Å and Uiso(H) = 1.2 or 1.5Ueq(C). The methyl groups were allowed to rotate around their local threefold axes. H atoms bound to N2, N2' and O2' were located in difference Fourier maps and refined without restraint. Atom H2O could not be treated in this way and so was placed geometrically and refined as riding, with O—H = 0.84 Å and Uiso(H) = 1.2Ueq(O). The site occupancy of the ethyl acetate molecule was constrained to 0.5 in order to produce reasonable displacement parameters. The geometry of this molecule was also restrained. The maxima in the final difference Fourier map are located around the solvent molecule. In the absence of significant anomalous scattering effects, Friedel pairs were merged as equivalent data. The absolute structure is assigned on the basis of known chirality of thymidine used in the chemical synthesis.

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2004); software used to prepare material for publication: SHELXTL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), showing displacement ellipsoids at the 30% probability level. H atoms have been omitted.
[Figure 2] Fig. 2. Overlay of molecules A (dark spheres; blue in the electronic version of the paper) and B (light spheres; red), showing the different orientations adopted by the dimethoxytrityl group. H atoms have been omitted.
[Figure 3] Fig. 3. The molecular packing of (I), showing the intermolecular hydrogen-bond network. H atoms not involved in hydrogen bonding have been omitted. [Please provide symmetry codes where needed]
[5'-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-2'-deoxy-β-D- threopentofuranosyl]thymine ethyl acetate 0.25-solvate top
Crystal data top
C31H32N2O7·0.25C4H8O2F(000) = 1200
Mr = 566.61Dx = 1.218 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 10255 reflections
a = 10.542 (2) Åθ = 2.3–29.1°
b = 17.931 (4) ŵ = 0.09 mm1
c = 17.136 (3) ÅT = 153 K
β = 107.51 (3)°Prism, colorless
V = 3089.1 (11) Å30.54 × 0.32 × 0.25 mm
Z = 4
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
6327 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.038
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
Detector resolution: 28.5714 pixels mm-1h = 1313
ϕ and ω scansk = 2319
24617 measured reflectionsl = 2222
7094 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.151 w = 1/[σ2(Fo2) + (0.0959P)2 + 0.869P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
7094 reflectionsΔρmax = 0.79 e Å3
790 parametersΔρmin = 0.32 e Å3
5 restraintsAbsolute structure: In the absence of significant anomalous scattering effects, Friedel pairs were merged as equivalent reflections.
Primary atom site location: structure-invariant direct methods
Crystal data top
C31H32N2O7·0.25C4H8O2V = 3089.1 (11) Å3
Mr = 566.61Z = 4
Monoclinic, P21Mo Kα radiation
a = 10.542 (2) ŵ = 0.09 mm1
b = 17.931 (4) ÅT = 153 K
c = 17.136 (3) Å0.54 × 0.32 × 0.25 mm
β = 107.51 (3)°
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
6327 reflections with I > 2σ(I)
24617 measured reflectionsRint = 0.038
7094 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0565 restraints
wR(F2) = 0.151H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.79 e Å3
7094 reflectionsΔρmin = 0.32 e Å3
790 parametersAbsolute structure: In the absence of significant anomalous scattering effects, Friedel pairs were merged as equivalent reflections.
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
xyzUiso*/UeqOcc. (<1)
O10.2151 (2)0.32719 (13)0.07146 (13)0.0218 (5)
O20.3666 (2)0.32102 (15)0.20273 (16)0.0301 (5)
H2O0.44990.32210.19030.036*
O40.0951 (2)0.23199 (14)0.20216 (15)0.0276 (5)
O30.3646 (2)0.38126 (18)0.11039 (18)0.0392 (7)
O50.2788 (2)0.48282 (13)0.03782 (13)0.0241 (5)
O60.3179 (3)0.44313 (19)0.32883 (17)0.0444 (7)
O70.0999 (3)0.75605 (18)0.14832 (18)0.0483 (8)
N10.0087 (3)0.34228 (16)0.14261 (17)0.0215 (6)
N20.2275 (3)0.31054 (17)0.15847 (18)0.0242 (6)
H2N0.298 (4)0.275 (2)0.180 (2)0.026 (10)*
C10.3396 (3)0.36087 (18)0.07274 (19)0.0201 (6)
H10.41120.32230.05530.024*
C20.3219 (3)0.38051 (19)0.1624 (2)0.0226 (6)
H20.36600.42880.16770.027*
C30.1723 (3)0.3848 (2)0.19975 (19)0.0230 (6)
H3A0.14550.37230.25870.028*
H3B0.13850.43500.19270.028*
C40.1227 (3)0.32666 (19)0.15144 (19)0.0204 (6)
H40.12240.27640.17690.025*
C80.1086 (3)0.29146 (19)0.17000 (19)0.0210 (6)
C50.0272 (3)0.40655 (19)0.1018 (2)0.0254 (7)
H50.04560.43990.08260.030*
C60.1424 (3)0.4238 (2)0.0883 (2)0.0292 (7)
C70.2540 (3)0.3730 (2)0.1176 (2)0.0284 (7)
C90.1611 (4)0.4934 (3)0.0439 (3)0.0441 (11)
H9A0.16750.48010.01030.053*
H9B0.24290.51870.07530.053*
H9C0.08500.52670.03770.053*
C100.3738 (3)0.42424 (19)0.0119 (2)0.0238 (7)
H10A0.37390.40610.04270.029*
H10B0.46390.44330.00740.029*
C110.3062 (3)0.54958 (19)0.0126 (2)0.0246 (7)
C120.4332 (4)0.58728 (19)0.0058 (2)0.0274 (7)
C130.5132 (4)0.6323 (2)0.0675 (3)0.0364 (9)
H130.49200.63810.11730.044*
C140.6222 (5)0.6685 (2)0.0574 (3)0.0465 (11)
H140.67710.69780.10060.056*
C150.6519 (5)0.6622 (3)0.0151 (4)0.0509 (12)
H150.72780.68680.02170.061*
C160.5721 (5)0.6204 (2)0.0782 (3)0.0458 (11)
H160.59130.61740.12890.055*
C170.4633 (4)0.5824 (2)0.0679 (2)0.0348 (8)
H170.40910.55290.11130.042*
C180.3099 (3)0.52775 (19)0.1004 (2)0.0240 (7)
C190.4273 (4)0.5060 (2)0.1590 (2)0.0275 (7)
H190.50940.51000.14700.033*
C200.4265 (4)0.4785 (2)0.2343 (2)0.0327 (8)
H200.50770.46420.27330.039*
C210.3083 (4)0.4719 (2)0.2531 (2)0.0303 (8)
C220.1906 (4)0.4939 (2)0.1965 (2)0.0310 (8)
H220.10920.49070.20930.037*
C230.1924 (4)0.5210 (2)0.1202 (2)0.0282 (7)
H230.11110.53510.08110.034*
C240.1951 (5)0.4262 (3)0.3457 (3)0.0541 (12)
H24A0.14750.47260.34830.065*
H24B0.21460.40000.39820.065*
H24C0.13990.39440.30210.065*
C250.1916 (4)0.60279 (19)0.0278 (2)0.0260 (7)
C260.1615 (4)0.6628 (2)0.0147 (2)0.0371 (9)
H260.20870.66880.07100.045*
C270.0645 (4)0.7142 (2)0.0231 (2)0.0388 (9)
H270.04480.75430.00760.047*
C280.0043 (4)0.7073 (2)0.1058 (2)0.0345 (8)
C290.0274 (4)0.6495 (2)0.1499 (2)0.0404 (9)
H290.01610.64550.20700.048*
C300.1222 (4)0.5976 (2)0.1111 (2)0.0340 (8)
H300.14080.55720.14190.041*
C310.1295 (5)0.8176 (3)0.1044 (3)0.0498 (11)
H31A0.15930.79930.05890.060*
H31B0.20010.84780.14110.060*
H31C0.04960.84820.08280.060*
O1'0.7264 (2)0.08358 (14)0.32231 (15)0.0271 (5)
O2'0.9396 (3)0.20564 (18)0.31128 (18)0.0397 (7)
H2'O1.024 (5)0.189 (3)0.310 (3)0.048 (14)*
O3'0.1955 (2)0.11553 (16)0.37975 (17)0.0343 (6)
O4'0.4300 (2)0.20799 (15)0.22002 (14)0.0263 (5)
O5'0.8659 (2)0.05605 (15)0.48853 (14)0.0274 (5)
O6'1.4497 (3)0.0349 (2)0.6915 (2)0.0564 (10)
O7'0.6227 (5)0.1702 (3)0.7502 (3)0.0826 (14)
N1'0.5462 (3)0.15000 (16)0.33837 (16)0.0220 (6)
N2'0.3184 (3)0.16005 (17)0.30231 (18)0.0232 (6)
H2'N0.253 (4)0.176 (2)0.274 (2)0.013 (9)*
C1'0.8694 (3)0.0862 (2)0.3544 (2)0.0256 (7)
H1'0.90750.07090.30990.031*
C2'0.9064 (3)0.1685 (2)0.3760 (2)0.0290 (8)
H2'0.97910.17320.42900.035*
C3'0.7779 (3)0.2028 (2)0.3811 (2)0.0259 (7)
H3'10.77180.25610.36550.031*
H3'20.76940.19790.43680.031*
C4'0.6731 (3)0.15678 (19)0.3196 (2)0.0229 (6)
H4'0.65680.17820.26350.028*
C5'0.5434 (3)0.1157 (2)0.4100 (2)0.0247 (7)
H5'0.62560.10070.44770.030*
C6'0.4316 (3)0.1022 (2)0.4298 (2)0.0274 (7)
C7'0.3057 (3)0.12454 (19)0.3711 (2)0.0249 (7)
C8'0.4313 (3)0.17471 (18)0.2828 (2)0.0220 (6)
C9'0.4293 (4)0.0644 (3)0.5067 (3)0.0413 (10)
H9'10.52060.05450.54070.050*
H9'20.38060.01720.49340.050*
H9'30.38500.09660.53670.050*
C10'0.9179 (4)0.0321 (2)0.4247 (2)0.0275 (7)
H10C0.88650.01890.40680.033*
H10D1.01630.03170.44440.033*
C11'0.8902 (3)0.0099 (2)0.5610 (2)0.0291 (8)
C12'0.8104 (4)0.0631 (2)0.5410 (2)0.0341 (8)
C13'0.8453 (4)0.1265 (3)0.5898 (3)0.0465 (11)
H13'0.92550.12620.63400.056*
C14'0.7669 (5)0.1896 (3)0.5759 (4)0.0620 (15)
H14'0.79350.23210.61000.074*
C15'0.6482 (5)0.1908 (3)0.5116 (4)0.0662 (16)
H15'0.59200.23340.50250.079*
C16'0.6136 (4)0.1287 (3)0.4610 (3)0.0502 (11)
H16'0.53470.12940.41590.060*
C17'0.6932 (4)0.0661 (2)0.4760 (2)0.0364 (9)
H17'0.66750.02400.44120.044*
C18'1.0409 (4)0.0040 (2)0.5970 (2)0.0318 (8)
C19'1.1023 (4)0.0619 (2)0.5687 (2)0.0352 (8)
H19'1.04960.09460.52830.042*
C20'1.2394 (4)0.0734 (3)0.5980 (3)0.0383 (9)
H20'1.27920.11310.57700.046*
C21'1.3161 (4)0.0272 (3)0.6570 (3)0.0426 (11)
C22'1.2572 (4)0.0323 (3)0.6849 (3)0.0425 (10)
H22'1.31090.06550.72440.051*
C23'1.1215 (4)0.0436 (3)0.6559 (2)0.0363 (9)
H23'1.08250.08410.67620.044*
C24'1.5121 (5)0.0974 (4)0.6669 (4)0.0663 (18)
H24D1.47630.14360.68250.080*
H24E1.60830.09530.69380.080*
H24F1.49460.09630.60740.080*
C25'0.8318 (4)0.0558 (3)0.6168 (2)0.0339 (8)
C26'0.7903 (5)0.0218 (3)0.6793 (3)0.0480 (11)
H26'0.80830.02960.69110.058*
C27'0.7247 (6)0.0618 (4)0.7231 (3)0.0582 (13)
H27'0.69890.03830.76560.070*
C28'0.6955 (5)0.1366 (3)0.7056 (3)0.0509 (12)
C29'0.7421 (5)0.1716 (3)0.6489 (3)0.0520 (12)
H29'0.72730.22340.63910.062*
C30'0.8113 (5)0.1310 (3)0.6057 (2)0.0445 (10)
H30'0.84520.15610.56740.053*
C31'0.5816 (9)0.2452 (5)0.7312 (4)0.094 (3)
H31D0.65710.27500.72690.112*
H31E0.54890.26560.77460.112*
H31F0.51030.24680.67910.112*
O150.2273 (8)0.7847 (6)0.2520 (7)0.084 (3)0.50
O160.0726 (15)0.8569 (8)0.3339 (12)0.155 (6)0.50
C630.2266 (16)0.8284 (16)0.1824 (12)0.155 (6)0.50
H63A0.13770.82670.17400.186*0.50
H63B0.24840.88100.19050.186*0.50
C640.3286 (10)0.7960 (6)0.1105 (7)0.059 (3)0.50
H64A0.31040.74280.10620.071*0.50
H64B0.32550.82170.06060.071*0.50
H64C0.41700.80210.11730.071*0.50
C650.1420 (14)0.8015 (9)0.3250 (8)0.140 (11)0.50
C660.128 (2)0.7486 (11)0.3939 (10)0.146 (10)0.50
H66A0.03570.74790.42880.175*0.50
H66B0.15430.69850.37210.175*0.50
H66C0.18600.76460.42620.175*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0175 (10)0.0245 (11)0.0224 (11)0.0002 (9)0.0046 (9)0.0009 (9)
O20.0220 (11)0.0368 (14)0.0341 (13)0.0035 (11)0.0127 (10)0.0072 (11)
O40.0183 (11)0.0297 (12)0.0365 (13)0.0040 (10)0.0108 (10)0.0108 (11)
O30.0180 (12)0.0503 (17)0.0509 (16)0.0013 (12)0.0130 (11)0.0166 (14)
O50.0272 (12)0.0192 (11)0.0220 (11)0.0017 (9)0.0015 (9)0.0031 (9)
O60.0509 (18)0.0556 (19)0.0279 (13)0.0011 (15)0.0136 (13)0.0119 (13)
O70.064 (2)0.0425 (17)0.0316 (14)0.0248 (15)0.0038 (13)0.0005 (13)
N10.0152 (12)0.0240 (13)0.0257 (13)0.0010 (10)0.0067 (10)0.0052 (11)
N20.0156 (12)0.0295 (14)0.0266 (14)0.0033 (12)0.0048 (11)0.0041 (11)
C10.0151 (14)0.0203 (14)0.0234 (14)0.0006 (12)0.0038 (11)0.0003 (12)
C20.0173 (14)0.0259 (16)0.0258 (15)0.0031 (13)0.0080 (12)0.0043 (13)
C30.0192 (15)0.0296 (16)0.0199 (14)0.0016 (13)0.0055 (12)0.0003 (13)
C40.0115 (13)0.0241 (15)0.0248 (15)0.0018 (12)0.0042 (11)0.0042 (12)
C80.0188 (15)0.0256 (16)0.0191 (14)0.0041 (13)0.0063 (12)0.0018 (12)
C50.0179 (15)0.0249 (16)0.0319 (17)0.0008 (13)0.0055 (13)0.0047 (13)
C60.0204 (16)0.0334 (18)0.0321 (17)0.0016 (14)0.0054 (13)0.0095 (15)
C70.0209 (16)0.0349 (18)0.0292 (17)0.0003 (14)0.0072 (13)0.0042 (14)
C90.0244 (18)0.046 (2)0.062 (3)0.0028 (18)0.0135 (18)0.025 (2)
C100.0228 (15)0.0220 (15)0.0234 (15)0.0000 (13)0.0025 (12)0.0016 (12)
C110.0279 (16)0.0217 (15)0.0220 (15)0.0011 (13)0.0041 (13)0.0034 (12)
C120.0339 (18)0.0191 (15)0.0307 (17)0.0004 (14)0.0118 (14)0.0020 (13)
C130.041 (2)0.0261 (18)0.043 (2)0.0093 (17)0.0150 (18)0.0090 (16)
C140.041 (2)0.030 (2)0.073 (3)0.0130 (18)0.024 (2)0.010 (2)
C150.048 (3)0.033 (2)0.082 (4)0.008 (2)0.036 (3)0.003 (2)
C160.054 (3)0.031 (2)0.064 (3)0.0059 (19)0.036 (2)0.008 (2)
C170.046 (2)0.0277 (18)0.0365 (19)0.0022 (17)0.0208 (17)0.0014 (15)
C180.0273 (17)0.0217 (15)0.0218 (15)0.0042 (13)0.0056 (13)0.0019 (12)
C190.0248 (16)0.0312 (18)0.0245 (16)0.0040 (14)0.0045 (13)0.0017 (13)
C200.0306 (19)0.039 (2)0.0242 (16)0.0026 (16)0.0017 (14)0.0024 (15)
C210.041 (2)0.0265 (17)0.0232 (16)0.0011 (15)0.0090 (15)0.0016 (13)
C220.0322 (19)0.0320 (18)0.0309 (17)0.0050 (15)0.0126 (15)0.0025 (15)
C230.0249 (17)0.0326 (18)0.0254 (16)0.0016 (14)0.0049 (13)0.0004 (14)
C240.070 (3)0.058 (3)0.044 (2)0.005 (3)0.031 (2)0.012 (2)
C250.0301 (17)0.0219 (15)0.0243 (16)0.0013 (14)0.0057 (13)0.0015 (12)
C260.051 (2)0.0319 (19)0.0242 (17)0.0094 (18)0.0048 (16)0.0017 (15)
C270.051 (2)0.032 (2)0.0304 (18)0.0151 (18)0.0087 (17)0.0042 (16)
C280.042 (2)0.0321 (18)0.0273 (17)0.0109 (17)0.0083 (16)0.0037 (15)
C290.050 (2)0.041 (2)0.0245 (17)0.0100 (19)0.0022 (16)0.0009 (16)
C300.046 (2)0.0270 (17)0.0259 (17)0.0103 (16)0.0053 (15)0.0045 (14)
C310.066 (3)0.040 (2)0.043 (2)0.027 (2)0.014 (2)0.0032 (19)
O1'0.0192 (11)0.0308 (13)0.0296 (12)0.0051 (10)0.0047 (9)0.0015 (10)
O2'0.0298 (14)0.0503 (17)0.0455 (16)0.0008 (13)0.0211 (13)0.0188 (14)
O3'0.0206 (12)0.0407 (15)0.0460 (15)0.0020 (11)0.0167 (11)0.0117 (12)
O4'0.0224 (11)0.0348 (13)0.0224 (11)0.0085 (10)0.0078 (9)0.0092 (10)
O5'0.0267 (12)0.0359 (13)0.0210 (11)0.0075 (11)0.0094 (9)0.0097 (10)
O6'0.0225 (14)0.082 (3)0.062 (2)0.0028 (16)0.0080 (13)0.0292 (19)
O7'0.098 (3)0.107 (4)0.057 (2)0.029 (3)0.046 (2)0.001 (2)
N1'0.0160 (13)0.0287 (14)0.0220 (13)0.0032 (11)0.0066 (10)0.0060 (11)
N2'0.0131 (13)0.0313 (15)0.0239 (13)0.0037 (12)0.0038 (11)0.0051 (12)
C1'0.0163 (15)0.0386 (19)0.0226 (15)0.0065 (14)0.0068 (12)0.0072 (14)
C2'0.0175 (15)0.043 (2)0.0251 (16)0.0008 (15)0.0046 (13)0.0101 (15)
C3'0.0197 (16)0.0334 (17)0.0260 (16)0.0021 (14)0.0089 (13)0.0035 (14)
C4'0.0185 (15)0.0266 (16)0.0259 (15)0.0044 (13)0.0101 (12)0.0058 (13)
C5'0.0213 (16)0.0299 (17)0.0236 (15)0.0043 (13)0.0078 (13)0.0053 (13)
C6'0.0225 (16)0.0316 (18)0.0288 (16)0.0024 (14)0.0089 (13)0.0097 (14)
C7'0.0208 (16)0.0244 (16)0.0312 (17)0.0007 (13)0.0103 (13)0.0051 (13)
C8'0.0188 (15)0.0224 (15)0.0233 (15)0.0003 (12)0.0043 (12)0.0006 (12)
C9'0.032 (2)0.059 (3)0.038 (2)0.0031 (19)0.0184 (17)0.019 (2)
C10'0.0278 (17)0.0347 (18)0.0216 (15)0.0124 (15)0.0098 (13)0.0074 (13)
C11'0.0227 (16)0.039 (2)0.0231 (16)0.0016 (15)0.0038 (13)0.0127 (14)
C12'0.0249 (17)0.042 (2)0.0346 (19)0.0053 (16)0.0081 (15)0.0133 (17)
C13'0.030 (2)0.052 (3)0.050 (2)0.0005 (19)0.0014 (18)0.027 (2)
C14'0.046 (3)0.051 (3)0.079 (4)0.004 (2)0.003 (2)0.032 (3)
C15'0.044 (3)0.050 (3)0.096 (4)0.011 (2)0.008 (3)0.022 (3)
C16'0.035 (2)0.045 (2)0.060 (3)0.000 (2)0.001 (2)0.008 (2)
C17'0.0288 (18)0.036 (2)0.040 (2)0.0058 (16)0.0030 (16)0.0146 (17)
C18'0.0259 (17)0.044 (2)0.0251 (16)0.0009 (16)0.0066 (14)0.0174 (15)
C19'0.0284 (18)0.042 (2)0.0351 (19)0.0057 (16)0.0085 (15)0.0144 (17)
C20'0.032 (2)0.043 (2)0.042 (2)0.0082 (18)0.0142 (17)0.0207 (18)
C21'0.0230 (18)0.063 (3)0.041 (2)0.0021 (19)0.0096 (16)0.029 (2)
C22'0.033 (2)0.054 (3)0.034 (2)0.0126 (19)0.0014 (16)0.0111 (19)
C23'0.0282 (18)0.047 (2)0.0316 (18)0.0019 (17)0.0058 (15)0.0132 (17)
C24'0.034 (2)0.094 (4)0.074 (4)0.020 (3)0.021 (2)0.047 (3)
C25'0.0251 (17)0.056 (2)0.0198 (16)0.0034 (17)0.0057 (13)0.0060 (16)
C26'0.053 (3)0.058 (3)0.037 (2)0.001 (2)0.019 (2)0.012 (2)
C27'0.067 (3)0.079 (4)0.038 (2)0.006 (3)0.029 (2)0.008 (2)
C28'0.048 (3)0.071 (3)0.039 (2)0.012 (2)0.023 (2)0.003 (2)
C29'0.060 (3)0.060 (3)0.032 (2)0.013 (2)0.008 (2)0.006 (2)
C30'0.048 (2)0.059 (3)0.0283 (19)0.012 (2)0.0136 (18)0.0023 (18)
C31'0.120 (6)0.102 (6)0.061 (4)0.065 (5)0.031 (4)0.005 (4)
O150.049 (4)0.094 (7)0.112 (8)0.006 (5)0.029 (5)0.032 (6)
O160.121 (9)0.153 (11)0.229 (15)0.044 (8)0.110 (10)0.094 (11)
C630.121 (9)0.153 (11)0.229 (15)0.044 (8)0.110 (10)0.094 (11)
C640.046 (5)0.054 (6)0.084 (8)0.007 (5)0.027 (5)0.011 (6)
C650.119 (16)0.112 (16)0.24 (3)0.051 (13)0.13 (2)0.086 (18)
C660.16 (2)0.16 (2)0.101 (14)0.056 (17)0.015 (13)0.063 (15)
Geometric parameters (Å, º) top
O1—C11.452 (4)O5'—C11'1.450 (4)
O1—C41.422 (4)O6'—C21'1.361 (5)
O2—C21.426 (4)O6'—C24'1.427 (8)
O2—H2O0.8400O7'—C28'1.374 (6)
O4—C81.228 (4)O7'—C31'1.420 (9)
O3—C71.218 (4)N1'—C8'1.370 (4)
O5—C101.427 (4)N1'—C5'1.382 (4)
O5—C111.453 (4)N1'—C4'1.471 (4)
O6—C211.372 (4)N2'—C8'1.355 (4)
O6—C241.441 (6)N2'—C7'1.382 (4)
O7—C281.368 (5)N2'—H2'N0.77 (4)
O7—C311.424 (5)C1'—C10'1.511 (4)
N1—C81.364 (4)C1'—C2'1.543 (5)
N1—C51.392 (4)C1'—H1'1.0000
N1—C41.466 (4)C2'—C3'1.514 (5)
N2—C81.370 (4)C2'—H2'1.0000
N2—C71.393 (5)C3'—C4'1.520 (5)
N2—H2N0.96 (4)C3'—H3'10.9900
C1—C101.511 (4)C3'—H3'20.9900
C1—C21.531 (4)C4'—H4'1.0000
C1—H11.0000C5'—C6'1.342 (5)
C2—C31.515 (4)C5'—H5'0.9500
C2—H21.0000C6'—C7'1.459 (5)
C3—C41.518 (5)C6'—C9'1.489 (5)
C3—H3A0.9900C9'—H9'10.9800
C3—H3B0.9900C9'—H9'20.9800
C4—H41.0000C9'—H9'30.9800
C5—C61.340 (5)C10'—H10C0.9900
C5—H50.9500C10'—H10D0.9900
C6—C71.453 (5)C11'—C25'1.525 (6)
C6—C91.505 (5)C11'—C12'1.538 (6)
C9—H9A0.9800C11'—C18'1.541 (5)
C9—H9B0.9800C12'—C17'1.394 (5)
C9—H9C0.9800C12'—C13'1.394 (5)
C10—H10A0.9900C13'—C14'1.379 (7)
C10—H10B0.9900C13'—H13'0.9500
C11—C251.532 (5)C14'—C15'1.397 (7)
C11—C121.535 (5)C14'—H14'0.9500
C11—C181.543 (5)C15'—C16'1.390 (7)
C12—C131.394 (5)C15'—H15'0.9500
C12—C171.395 (5)C16'—C17'1.379 (6)
C13—C141.375 (6)C16'—H16'0.9500
C13—H130.9500C17'—H17'0.9500
C14—C151.375 (7)C18'—C19'1.385 (6)
C14—H140.9500C18'—C23'1.398 (6)
C15—C161.375 (7)C19'—C20'1.395 (5)
C15—H150.9500C19'—H19'0.9500
C16—C171.391 (6)C20'—C21'1.367 (7)
C16—H160.9500C20'—H20'0.9500
C17—H170.9500C21'—C22'1.391 (7)
C18—C231.385 (5)C22'—C23'1.381 (6)
C18—C191.395 (5)C22'—H22'0.9500
C19—C201.383 (5)C23'—H23'0.9500
C19—H190.9500C24'—H24D0.9800
C20—C211.383 (6)C24'—H24E0.9800
C20—H200.9500C24'—H24F0.9800
C21—C221.383 (5)C25'—C30'1.369 (7)
C22—C231.400 (5)C25'—C26'1.411 (6)
C22—H220.9500C26'—C27'1.367 (7)
C23—H230.9500C26'—H26'0.9500
C24—H24A0.9800C27'—C28'1.388 (8)
C24—H24B0.9800C27'—H27'0.9500
C24—H24C0.9800C28'—C29'1.366 (7)
C25—C261.389 (5)C29'—C30'1.392 (7)
C25—C301.397 (5)C29'—H29'0.9500
C26—C271.384 (6)C30'—H30'0.9500
C26—H260.9500C31'—H31D0.9800
C27—C281.388 (5)C31'—H31E0.9800
C27—H270.9500C31'—H31F0.9800
C28—C291.382 (6)O15—C651.338 (3)
C29—C301.381 (5)O15—C631.43 (3)
C29—H290.9500O16—C651.216 (3)
C30—H300.9500C63—C641.489 (3)
C31—H31A0.9800C63—H63A0.9900
C31—H31B0.9800C63—H63B0.9900
C31—H31C0.9800C64—H64A0.9800
O1'—C1'1.442 (4)C64—H64B0.9800
O1'—C4'1.423 (4)C64—H64C0.9800
O2'—C2'1.424 (4)C65—C661.486 (3)
O2'—H2'O0.95 (5)C66—H66A0.9800
O3'—C7'1.225 (4)C66—H66B0.9800
O4'—C8'1.227 (4)C66—H66C0.9800
O5'—C10'1.429 (4)
C4—O1—C1110.4 (2)O1'—C1'—C10'110.3 (3)
C2—O2—H2O109.5O1'—C1'—C2'106.4 (3)
C10—O5—C11115.2 (2)C10'—C1'—C2'115.0 (3)
C21—O6—C24117.0 (3)O1'—C1'—H1'108.3
C28—O7—C31117.2 (3)C10'—C1'—H1'108.3
C8—N1—C5121.1 (3)C2'—C1'—H1'108.3
C8—N1—C4119.5 (3)O2'—C2'—C3'106.8 (3)
C5—N1—C4119.3 (3)O2'—C2'—C1'111.3 (3)
C8—N2—C7127.1 (3)C3'—C2'—C1'103.6 (3)
C8—N2—H2N115 (2)O2'—C2'—H2'111.6
C7—N2—H2N118 (2)C3'—C2'—H2'111.6
O1—C1—C10109.4 (3)C1'—C2'—H2'111.6
O1—C1—C2105.8 (2)C2'—C3'—C4'102.5 (3)
C10—C1—C2116.8 (3)C2'—C3'—H3'1111.3
O1—C1—H1108.2C4'—C3'—H3'1111.3
C10—C1—H1108.2C2'—C3'—H3'2111.3
C2—C1—H1108.2C4'—C3'—H3'2111.3
O2—C2—C3106.6 (3)H3'1—C3'—H3'2109.2
O2—C2—C1110.8 (3)O1'—C4'—N1'107.0 (3)
C3—C2—C1103.5 (3)O1'—C4'—C3'106.3 (3)
O2—C2—H2111.8N1'—C4'—C3'114.3 (3)
C3—C2—H2111.8O1'—C4'—H4'109.7
C1—C2—H2111.8N1'—C4'—H4'109.7
C2—C3—C4102.7 (3)C3'—C4'—H4'109.7
C2—C3—H3A111.2C6'—C5'—N1'124.1 (3)
C4—C3—H3A111.2C6'—C5'—H5'118.0
C2—C3—H3B111.2N1'—C5'—H5'118.0
C4—C3—H3B111.2C5'—C6'—C7'117.5 (3)
H3A—C3—H3B109.1C5'—C6'—C9'123.7 (3)
O1—C4—N1107.1 (2)C7'—C6'—C9'118.7 (3)
O1—C4—C3105.8 (2)O3'—C7'—N2'120.2 (3)
N1—C4—C3114.6 (3)O3'—C7'—C6'125.4 (3)
O1—C4—H4109.7N2'—C7'—C6'114.4 (3)
N1—C4—H4109.7O4'—C8'—N2'122.1 (3)
C3—C4—H4109.7O4'—C8'—N1'122.7 (3)
O4—C8—N1123.6 (3)N2'—C8'—N1'115.2 (3)
O4—C8—N2121.1 (3)C6'—C9'—H9'1109.5
N1—C8—N2115.4 (3)C6'—C9'—H9'2109.5
C6—C5—N1123.3 (3)H9'1—C9'—H9'2109.5
C6—C5—H5118.3C6'—C9'—H9'3109.5
N1—C5—H5118.3H9'1—C9'—H9'3109.5
C5—C6—C7118.5 (3)H9'2—C9'—H9'3109.5
C5—C6—C9122.8 (3)O5'—C10'—C1'107.6 (3)
C7—C6—C9118.7 (3)O5'—C10'—H10C110.2
O3—C7—N2119.4 (3)C1'—C10'—H10C110.2
O3—C7—C6126.0 (3)O5'—C10'—H10D110.2
N2—C7—C6114.5 (3)C1'—C10'—H10D110.2
C6—C9—H9A109.5H10C—C10'—H10D108.5
C6—C9—H9B109.5O5'—C11'—C25'103.2 (3)
H9A—C9—H9B109.5O5'—C11'—C12'110.5 (3)
C6—C9—H9C109.5C25'—C11'—C12'107.7 (3)
H9A—C9—H9C109.5O5'—C11'—C18'109.3 (3)
H9B—C9—H9C109.5C25'—C11'—C18'113.5 (3)
O5—C10—C1109.8 (3)C12'—C11'—C18'112.4 (3)
O5—C10—H10A109.7C17'—C12'—C13'117.3 (4)
C1—C10—H10A109.7C17'—C12'—C11'120.4 (3)
O5—C10—H10B109.7C13'—C12'—C11'122.1 (3)
C1—C10—H10B109.7C14'—C13'—C12'121.9 (4)
H10A—C10—H10B108.2C14'—C13'—H13'119.0
O5—C11—C25104.8 (3)C12'—C13'—H13'119.0
O5—C11—C12109.9 (3)C13'—C14'—C15'119.9 (4)
C25—C11—C12106.2 (3)C13'—C14'—H14'120.1
O5—C11—C18108.2 (3)C15'—C14'—H14'120.1
C25—C11—C18112.6 (3)C16'—C15'—C14'118.9 (5)
C12—C11—C18114.7 (3)C16'—C15'—H15'120.5
C13—C12—C17118.2 (4)C14'—C15'—H15'120.5
C13—C12—C11122.7 (3)C17'—C16'—C15'120.4 (4)
C17—C12—C11118.8 (3)C17'—C16'—H16'119.8
C14—C13—C12121.1 (4)C15'—C16'—H16'119.8
C14—C13—H13119.5C16'—C17'—C12'121.6 (4)
C12—C13—H13119.5C16'—C17'—H17'119.2
C15—C14—C13120.1 (4)C12'—C17'—H17'119.2
C15—C14—H14120.0C19'—C18'—C23'117.6 (4)
C13—C14—H14120.0C19'—C18'—C11'121.0 (4)
C14—C15—C16120.2 (4)C23'—C18'—C11'121.3 (4)
C14—C15—H15119.9C18'—C19'—C20'121.9 (4)
C16—C15—H15119.9C18'—C19'—H19'119.1
C15—C16—C17120.0 (4)C20'—C19'—H19'119.1
C15—C16—H16120.0C21'—C20'—C19'119.6 (4)
C17—C16—H16120.0C21'—C20'—H20'120.2
C16—C17—C12120.4 (4)C19'—C20'—H20'120.2
C16—C17—H17119.8O6'—C21'—C20'124.5 (5)
C12—C17—H17119.8O6'—C21'—C22'116.0 (4)
C23—C18—C19117.6 (3)C20'—C21'—C22'119.6 (4)
C23—C18—C11119.9 (3)C23'—C22'—C21'120.7 (4)
C19—C18—C11122.0 (3)C23'—C22'—H22'119.7
C20—C19—C18121.2 (3)C21'—C22'—H22'119.7
C20—C19—H19119.4C22'—C23'—C18'120.6 (4)
C18—C19—H19119.4C22'—C23'—H23'119.7
C21—C20—C19120.5 (3)C18'—C23'—H23'119.7
C21—C20—H20119.8O6'—C24'—H24D109.5
C19—C20—H20119.8O6'—C24'—H24E109.5
O6—C21—C22124.5 (4)H24D—C24'—H24E109.5
O6—C21—C20116.0 (3)O6'—C24'—H24F109.5
C22—C21—C20119.6 (3)H24D—C24'—H24F109.5
C21—C22—C23119.5 (3)H24E—C24'—H24F109.5
C21—C22—H22120.2C30'—C25'—C26'117.3 (4)
C23—C22—H22120.2C30'—C25'—C11'121.4 (4)
C18—C23—C22121.6 (3)C26'—C25'—C11'121.2 (4)
C18—C23—H23119.2C27'—C26'—C25'120.9 (5)
C22—C23—H23119.2C27'—C26'—H26'119.5
O6—C24—H24A109.5C25'—C26'—H26'119.5
O6—C24—H24B109.5C26'—C27'—C28'120.3 (5)
H24A—C24—H24B109.5C26'—C27'—H27'119.8
O6—C24—H24C109.5C28'—C27'—H27'119.8
H24A—C24—H24C109.5C29'—C28'—O7'125.0 (5)
H24B—C24—H24C109.5C29'—C28'—C27'119.5 (5)
C26—C25—C30117.1 (3)O7'—C28'—C27'115.4 (5)
C26—C25—C11121.3 (3)C28'—C29'—C30'119.8 (5)
C30—C25—C11121.3 (3)C28'—C29'—H29'120.1
C27—C26—C25121.6 (3)C30'—C29'—H29'120.1
C27—C26—H26119.2C25'—C30'—C29'121.8 (4)
C25—C26—H26119.2C25'—C30'—H30'119.1
C26—C27—C28120.3 (4)C29'—C30'—H30'119.1
C26—C27—H27119.9O7'—C31'—H31D109.5
C28—C27—H27119.9O7'—C31'—H31E109.5
O7—C28—C29116.7 (3)H31D—C31'—H31E109.5
O7—C28—C27124.2 (4)O7'—C31'—H31F109.5
C29—C28—C27119.1 (4)H31D—C31'—H31F109.5
C30—C29—C28120.1 (3)H31E—C31'—H31F109.5
C30—C29—H29120.0C65—O15—C63119.1 (11)
C28—C29—H29120.0O15—C63—C64107.0 (16)
C29—C30—C25121.8 (3)O15—C63—H63A110.3
C29—C30—H30119.1C64—C63—H63A110.3
C25—C30—H30119.1O15—C63—H63B110.3
O7—C31—H31A109.5C64—C63—H63B110.3
O7—C31—H31B109.5H63A—C63—H63B108.6
H31A—C31—H31B109.5C63—C64—H64A109.5
O7—C31—H31C109.5C63—C64—H64B109.5
H31A—C31—H31C109.5H64A—C64—H64B109.5
H31B—C31—H31C109.5C63—C64—H64C109.5
C4'—O1'—C1'109.9 (3)H64A—C64—H64C109.5
C2'—O2'—H2'O109 (3)H64B—C64—H64C109.5
C10'—O5'—C11'118.3 (3)O16—C65—O15120.7 (15)
C21'—O6'—C24'117.3 (4)O16—C65—C66120.8 (16)
C28'—O7'—C31'118.1 (5)O15—C65—C66118.5 (13)
C8'—N1'—C5'120.7 (3)C65—C66—H66A109.5
C8'—N1'—C4'119.6 (3)C65—C66—H66B109.5
C5'—N1'—C4'119.7 (3)H66A—C66—H66B109.5
C8'—N2'—C7'128.1 (3)C65—C66—H66C109.5
C8'—N2'—H2'N117 (3)H66A—C66—H66C109.5
C7'—N2'—H2'N115 (3)H66B—C66—H66C109.5
C4—O1—C1—C10125.0 (3)O1'—C1'—C2'—O2'95.8 (3)
C4—O1—C1—C21.7 (3)C10'—C1'—C2'—O2'141.8 (3)
O1—C1—C2—O292.0 (3)O1'—C1'—C2'—C3'18.7 (3)
C10—C1—C2—O2146.0 (3)C10'—C1'—C2'—C3'103.7 (3)
O1—C1—C2—C322.0 (3)O2'—C2'—C3'—C4'86.9 (3)
C10—C1—C2—C3100.0 (3)C1'—C2'—C3'—C4'30.8 (3)
O2—C2—C3—C484.3 (3)C1'—O1'—C4'—N1'144.8 (3)
C1—C2—C3—C432.7 (3)C1'—O1'—C4'—C3'22.2 (3)
C1—O1—C4—N1142.2 (3)C8'—N1'—C4'—O1'121.5 (3)
C1—O1—C4—C319.5 (3)C5'—N1'—C4'—O1'55.5 (4)
C8—N1—C4—O1120.7 (3)C8'—N1'—C4'—C3'121.1 (3)
C5—N1—C4—O155.3 (4)C5'—N1'—C4'—C3'61.9 (4)
C8—N1—C4—C3122.3 (3)C2'—C3'—C4'—O1'33.2 (3)
C5—N1—C4—C361.8 (4)C2'—C3'—C4'—N1'151.0 (3)
C2—C3—C4—O132.6 (3)C8'—N1'—C5'—C6'1.9 (5)
C2—C3—C4—N1150.3 (3)C4'—N1'—C5'—C6'175.1 (3)
C5—N1—C8—O4175.7 (3)N1'—C5'—C6'—C7'0.7 (6)
C4—N1—C8—O40.2 (5)N1'—C5'—C6'—C9'179.3 (4)
C5—N1—C8—N23.5 (4)C8'—N2'—C7'—O3'180.0 (3)
C4—N1—C8—N2179.4 (3)C8'—N2'—C7'—C6'1.4 (5)
C7—N2—C8—O4174.8 (3)C5'—C6'—C7'—O3'179.3 (4)
C7—N2—C8—N14.5 (5)C9'—C6'—C7'—O3'0.7 (6)
C8—N1—C5—C61.5 (5)C5'—C6'—C7'—N2'2.2 (5)
C4—N1—C5—C6177.4 (3)C9'—C6'—C7'—N2'179.1 (4)
N1—C5—C6—C70.0 (6)C7'—N2'—C8'—O4'178.8 (3)
N1—C5—C6—C9179.9 (4)C7'—N2'—C8'—N1'1.0 (5)
C8—N2—C7—O3177.9 (3)C5'—N1'—C8'—O4'177.1 (3)
C8—N2—C7—C63.1 (5)C4'—N1'—C8'—O4'5.9 (5)
C5—C6—C7—O3179.5 (4)C5'—N1'—C8'—N2'2.7 (5)
C9—C6—C7—O30.6 (6)C4'—N1'—C8'—N2'174.3 (3)
C5—C6—C7—N20.6 (5)C11'—O5'—C10'—C1'175.5 (3)
C9—C6—C7—N2179.5 (4)O1'—C1'—C10'—O5'63.3 (4)
C11—O5—C10—C1175.7 (3)C2'—C1'—C10'—O5'57.0 (4)
O1—C1—C10—O566.4 (3)C10'—O5'—C11'—C25'175.3 (3)
C2—C1—C10—O553.7 (4)C10'—O5'—C11'—C12'69.9 (4)
C10—O5—C11—C25179.9 (3)C10'—O5'—C11'—C18'54.3 (4)
C10—O5—C11—C1266.2 (3)O5'—C11'—C12'—C17'26.2 (5)
C10—O5—C11—C1859.7 (4)C25'—C11'—C12'—C17'85.8 (4)
O5—C11—C12—C13153.9 (3)C18'—C11'—C12'—C17'148.5 (4)
C25—C11—C12—C1393.3 (4)O5'—C11'—C12'—C13'159.0 (4)
C18—C11—C12—C1331.8 (5)C25'—C11'—C12'—C13'89.0 (5)
O5—C11—C12—C1732.5 (4)C18'—C11'—C12'—C13'36.6 (5)
C25—C11—C12—C1780.3 (4)C17'—C12'—C13'—C14'1.0 (7)
C18—C11—C12—C17154.6 (3)C11'—C12'—C13'—C14'174.0 (5)
C17—C12—C13—C142.7 (6)C12'—C13'—C14'—C15'0.4 (9)
C11—C12—C13—C14176.4 (4)C13'—C14'—C15'—C16'2.0 (10)
C12—C13—C14—C151.8 (7)C14'—C15'—C16'—C17'2.1 (9)
C13—C14—C15—C160.6 (7)C15'—C16'—C17'—C12'0.7 (8)
C14—C15—C16—C172.0 (7)C13'—C12'—C17'—C16'0.9 (7)
C15—C16—C17—C121.0 (6)C11'—C12'—C17'—C16'174.2 (4)
C13—C12—C17—C161.4 (6)O5'—C11'—C18'—C19'85.6 (4)
C11—C12—C17—C16175.3 (4)C25'—C11'—C18'—C19'159.9 (3)
O5—C11—C18—C2382.0 (4)C12'—C11'—C18'—C19'37.5 (4)
C25—C11—C18—C2333.4 (4)O5'—C11'—C18'—C23'90.7 (4)
C12—C11—C18—C23154.9 (3)C25'—C11'—C18'—C23'23.8 (5)
O5—C11—C18—C1990.5 (4)C12'—C11'—C18'—C23'146.2 (3)
C25—C11—C18—C19154.2 (3)C23'—C18'—C19'—C20'0.7 (5)
C12—C11—C18—C1932.6 (5)C11'—C18'—C19'—C20'177.1 (3)
C23—C18—C19—C200.1 (5)C18'—C19'—C20'—C21'0.8 (6)
C11—C18—C19—C20172.6 (3)C24'—O6'—C21'—C20'3.0 (6)
C18—C19—C20—C210.2 (6)C24'—O6'—C21'—C22'177.2 (4)
C24—O6—C21—C228.2 (6)C19'—C20'—C21'—O6'177.8 (4)
C24—O6—C21—C20171.8 (4)C19'—C20'—C21'—C22'2.3 (6)
C19—C20—C21—O6179.1 (4)O6'—C21'—C22'—C23'177.8 (4)
C19—C20—C21—C220.9 (6)C20'—C21'—C22'—C23'2.4 (6)
O6—C21—C22—C23178.6 (4)C21'—C22'—C23'—C18'0.9 (6)
C20—C21—C22—C231.5 (6)C19'—C18'—C23'—C22'0.6 (5)
C19—C18—C23—C220.5 (5)C11'—C18'—C23'—C22'177.1 (3)
C11—C18—C23—C22173.3 (3)O5'—C11'—C25'—C30'20.2 (5)
C21—C22—C23—C181.3 (6)C12'—C11'—C25'—C30'137.1 (4)
O5—C11—C25—C26161.0 (3)C18'—C11'—C25'—C30'97.9 (4)
C12—C11—C25—C2682.7 (4)O5'—C11'—C25'—C26'156.4 (4)
C18—C11—C25—C2643.6 (5)C12'—C11'—C25'—C26'39.5 (5)
O5—C11—C25—C3025.7 (5)C18'—C11'—C25'—C26'85.4 (5)
C12—C11—C25—C3090.6 (4)C30'—C25'—C26'—C27'4.1 (7)
C18—C11—C25—C30143.1 (3)C11'—C25'—C26'—C27'172.7 (4)
C30—C25—C26—C271.7 (6)C25'—C26'—C27'—C28'1.2 (8)
C11—C25—C26—C27175.3 (4)C31'—O7'—C28'—C29'6.2 (9)
C25—C26—C27—C281.0 (7)C31'—O7'—C28'—C27'175.6 (6)
C31—O7—C28—C29177.4 (4)C26'—C27'—C28'—C29'5.2 (8)
C31—O7—C28—C270.2 (7)C26'—C27'—C28'—O7'176.5 (5)
C26—C27—C28—O7178.8 (4)O7'—C28'—C29'—C30'178.0 (5)
C26—C27—C28—C291.3 (7)C27'—C28'—C29'—C30'3.9 (8)
O7—C28—C29—C30179.5 (4)C26'—C25'—C30'—C29'5.5 (7)
C27—C28—C29—C302.8 (7)C11'—C25'—C30'—C29'171.3 (4)
C28—C29—C30—C252.1 (7)C28'—C29'—C30'—C25'1.6 (7)
C26—C25—C30—C290.2 (6)C65—O15—C63—C64178.8 (13)
C11—C25—C30—C29173.7 (4)C63—O15—C65—O166 (2)
C4'—O1'—C1'—C10'127.4 (3)C63—O15—C65—C66170.2 (16)
C4'—O1'—C1'—C2'2.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O40.96 (4)1.81 (4)2.774 (4)180 (5)
O2—H2O···O3i0.842.283.000 (4)144
O2—H2O···O4i0.842.543.029 (4)119
N2—H2N···O40.77 (4)2.02 (4)2.778 (4)172 (4)
O2—H2O···O3ii0.95 (5)2.27 (5)3.060 (4)141 (4)
O2—H2O···O4ii0.95 (5)2.33 (5)2.873 (4)116 (4)
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC31H32N2O7·0.25C4H8O2
Mr566.61
Crystal system, space groupMonoclinic, P21
Temperature (K)153
a, b, c (Å)10.542 (2), 17.931 (4), 17.136 (3)
β (°) 107.51 (3)
V3)3089.1 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.54 × 0.32 × 0.25
Data collection
DiffractometerRigaku AFC10/Saturn724+
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
24617, 7094, 6327
Rint0.038
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.151, 1.00
No. of reflections7094
No. of parameters790
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.79, 0.32
Absolute structureIn the absence of significant anomalous scattering effects, Friedel pairs were merged as equivalent reflections.

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2004), SHELXTL97 (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
O1—C11.452 (4)O1'—C1'1.442 (4)
O1—C41.422 (4)O1'—C4'1.423 (4)
C1—C21.531 (4)C1'—C2'1.543 (5)
C2—C31.515 (4)C2'—C3'1.514 (5)
C3—C41.518 (5)C3'—C4'1.520 (5)
C8—N1—C4—O1120.7 (3)C8'—N1'—C4'—O1'121.5 (3)
C11—O5—C10—C1175.7 (3)C11'—O5'—C10'—C1'175.5 (3)
O1—C1—C10—O566.4 (3)O1'—C1'—C10'—O5'63.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O4'0.96 (4)1.81 (4)2.774 (4)180 (5)
O2—H2O···O3i0.842.283.000 (4)144.00
O2—H2O···O4'i0.842.543.029 (4)119.00
N2'—H2'N···O40.77 (4)2.02 (4)2.778 (4)172 (4)
O2'—H2'O···O3'ii0.95 (5)2.27 (5)3.060 (4)141 (4)
O2'—H2'O···O4ii0.95 (5)2.33 (5)2.873 (4)116 (4)
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z.
 

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