2,3,4,6-Tetra-O-acetyl-2-phthalimido-β-d-glucopyran­oside

Gervasio, G.; Marabello, D.; Bertolotti, F.

doi:10.1107/S1600536810048099

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3299

https://doi.org/10.1107/S1600536810048099

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2,3,4,6-Tetra-O-acetyl-2-phthalimido-β-D-glucopyranoside

Giuliana Gervasio,^a ^* Domenica Marabello ^a and Federica Bertolotti ^a

^aDipartimento di Chimica I, F.M. e Centro CrisDi, University of Turin, Via P. Giuria 7, 10125, Torino, Italy
^*Correspondence e-mail: giuliana.gervasio@unito.it

(Received 10 November 2010; accepted 18 November 2010; online 27 November 2010)

In the crystal structure of the title compound, C₂₄H₂₇NO₁₁, a substituted tetraacetyl glucopyranoside derivative, weak intermolecular C—H⋯O hydrogen bonds link the molecules into ribbons propagated in [010]. The D configuration has been attributed on the basis of the synthesis and the β anomer has been determined from the structure.

Related literature

For the synthesis, see: Dahmen et al. (1983a ,b , 1984 ); Magnusson et al. (1981 ); Quagliotto et al. (2005 ). For related structures, see: Ambrosi et al. (2002 ); Halasz et al. (2005 ).

Experimental

Crystal data

C₂₄H₂₇NO₁₂
M_r = 521.47
Monoclinic, P 2₁
a = 10.6447 (8) Å
b = 8.3655 (8) Å
c = 14.0123 (13) Å
β = 92.263 (2)°
V = 1246.80 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.34 × 0.22 × 0.20 mm

Data collection

Bruker APEX diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.77, T_max = 1.00
15243 measured reflections
3092 independent reflections
2238 reflections with I > 2σ(I)
R_int = 0.036
20 standard reflections every 60 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.132
S = 1.07
3092 reflections
334 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C32—H32B⋯O42ⁱ	0.96	2.45	3.317 (5)	151
C43—H43C⋯O42ⁱⁱ	0.96	2.48	3.284 (5)	141
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810048099/cv2796sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048099/cv2796Isup2.hkl

checkCIF report

Comment top

The title compound, 2-phthalimido-2,3,4,6-tetraacetyl-β-D-glucopyranoside, synthesized according to Dahmen et al. (1983a,b; 1984), Magnusson et al. (1981) and Quagliotto et al. (2005), belongs to the wide category of substituted tetraacetyl D-glucopyranoside compounds and the β anomer has been detected. Bond lengths and angles agree with those observed in numerous similar compounds, for instance, see Ambrosi et al. (2002) and Halasz et al. (2005). In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into ribbons propagated in [010] direction.

Related literature top

For the synthesis, see: Dahmen et al. (1983a,b, 1984); Magnusson et al. (1981); Quagliotto et al. (2005). For related structures, see: Ambrosi et al. (2002); Halasz et al. (2005).

Experimental top

The title compound has been obtained according to Dahmen et al. (1983a,b;1984) and Magnusson et al. (1981).

Structure description top

For the synthesis, see: Dahmen et al. (1983a,b, 1984); Magnusson et al. (1981); Quagliotto et al. (2005). For related structures, see: Ambrosi et al. (2002); Halasz et al. (2005).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing the atomic numbering and 30% probability displacements ellipsoids.

2,3,4,6-tetra-O-acetyl-2-phthalimido-β-D-glucopyranoside top

Crystal data top

C₂₄H₂₇NO₁₂	F(000) = 548
M_r = 521.47	D_x = 1.389 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 10.6447 (8) Å	Cell parameters from 400 reflections
b = 8.3655 (8) Å	θ = 3.0–23.0°
c = 14.0123 (13) Å	µ = 0.11 mm⁻¹
β = 92.263 (2)°	T = 293 K
V = 1246.80 (19) Å³	Prism, colourless
Z = 2	0.34 × 0.22 × 0.20 mm

Data collection top

Bruker APEX diffractometer	2238 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 28.3°, θ_min = 1.5°
φ scans	h = −14→14
Absorption correction: multi-scan (Blessing, 1995)	k = 0→10
T_min = 0.77, T_max = 1.00	l = 0→18
15243 measured reflections	20 standard reflections every 60 min
3092 independent reflections	intensity decay: none

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0605P)² + 0.1789P] where P = (F_o² + 2F_c²)/3
3092 reflections	(Δ/σ)_max < 0.001
334 parameters	Δρ_max = 0.16 e Å⁻³
1 restraint	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₄H₂₇NO₁₂	V = 1246.80 (19) Å³
M_r = 521.47	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.6447 (8) Å	µ = 0.11 mm⁻¹
b = 8.3655 (8) Å	T = 293 K
c = 14.0123 (13) Å	0.34 × 0.22 × 0.20 mm
β = 92.263 (2)°

Data collection top

Bruker APEX diffractometer	2238 reflections with I > 2σ(I)
Absorption correction: multi-scan (Blessing, 1995)	R_int = 0.036
T_min = 0.77, T_max = 1.00	20 standard reflections every 60 min
15243 measured reflections	intensity decay: none
3092 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	1 restraint
wR(F²) = 0.132	H-atom parameters constrained
S = 1.07	Δρ_max = 0.16 e Å⁻³
3092 reflections	Δρ_min = −0.14 e Å⁻³
334 parameters

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	0.2629 (2)	0.7283 (3)	0.24007 (16)	0.0505 (6)
C1	0.3802 (3)	0.8111 (5)	0.2432 (3)	0.0491 (9)
H1A	0.4463	0.7458	0.2745	0.059*
C2	0.3624 (3)	0.9652 (5)	0.2968 (3)	0.0451 (8)
H2A	0.2983	1.0301	0.2628	0.054*
C3	0.3214 (3)	0.9325 (4)	0.3972 (2)	0.0411 (8)
H3A	0.3905	0.8841	0.4355	0.049*
C4	0.2076 (3)	0.8243 (4)	0.3953 (2)	0.0440 (8)
H4A	0.1333	0.8839	0.3722	0.053*
C5	0.2261 (3)	0.6792 (5)	0.3325 (3)	0.0478 (9)
H5A	0.2926	0.6121	0.3617	0.057*
O2	0.4087 (2)	0.8446 (3)	0.14973 (17)	0.0539 (6)
C6	0.4639 (3)	0.7116 (6)	0.1020 (3)	0.0569 (10)
H6A	0.4232	0.6130	0.1201	0.068*
H6B	0.5526	0.7038	0.1201	0.068*
C7	0.4476 (3)	0.7368 (6)	−0.0042 (3)	0.0567 (10)
H7A	0.4802	0.8412	−0.0202	0.068*
H7B	0.4963	0.6571	−0.0368	0.068*
N1	0.3179 (3)	0.7261 (5)	−0.0376 (2)	0.0558 (8)
C8	0.2422 (4)	0.8575 (7)	−0.0603 (3)	0.0635 (11)
O8	0.2759 (4)	0.9941 (5)	−0.0599 (3)	0.0899 (11)
C9	0.1155 (4)	0.7921 (7)	−0.0853 (3)	0.0689 (13)
C10	0.1218 (4)	0.6290 (7)	−0.0788 (3)	0.0733 (14)
C11	0.2527 (4)	0.5832 (7)	−0.0482 (3)	0.0692 (12)
O11	0.2974 (3)	0.4522 (5)	−0.0343 (3)	0.0964 (12)
C12	0.0040 (5)	0.8685 (10)	−0.1087 (4)	0.0963 (19)
H12A	−0.0010	0.9791	−0.1143	0.116*
C13	−0.1025 (5)	0.7692 (14)	−0.1237 (4)	0.115 (3)
H13A	−0.1801	0.8165	−0.1376	0.138*
C14	−0.0955 (6)	0.6067 (15)	−0.1183 (5)	0.120 (3)
H14A	−0.1676	0.5455	−0.1294	0.144*
C15	0.0174 (5)	0.5328 (10)	−0.0968 (4)	0.102 (2)
H15A	0.0236	0.4220	−0.0943	0.122*
O21	0.4786 (2)	1.0518 (3)	0.30267 (17)	0.0527 (7)
O22	0.3877 (4)	1.2729 (5)	0.2431 (3)	0.1135 (15)
C21	0.4783 (4)	1.2067 (6)	0.2740 (3)	0.0664 (12)
C22	0.6057 (4)	1.2786 (8)	0.2884 (4)	0.0924 (17)
H22A	0.6036	1.3881	0.2677	0.139*
H22B	0.6647	1.2201	0.2518	0.139*
H22C	0.6310	1.2740	0.3549	0.139*
O31	0.28641 (18)	1.0835 (3)	0.43790 (17)	0.0484 (6)
O32	0.4534 (2)	1.0863 (4)	0.5412 (2)	0.0775 (9)
C31	0.3644 (3)	1.1517 (5)	0.5057 (3)	0.0482 (9)
C32	0.3233 (3)	1.3171 (5)	0.5245 (3)	0.0676 (12)
H32A	0.3785	1.3645	0.5723	0.101*
H32B	0.2391	1.3158	0.5466	0.101*
H32C	0.3255	1.3785	0.4667	0.101*
O41	0.18882 (19)	0.7666 (3)	0.49050 (17)	0.0511 (6)
O42	−0.0121 (3)	0.8438 (5)	0.4827 (2)	0.0779 (9)
C42	0.0715 (3)	0.7777 (5)	0.5246 (3)	0.0519 (9)
C43	0.0626 (4)	0.6939 (6)	0.6176 (3)	0.0714 (12)
H43A	−0.0213	0.7039	0.6396	0.107*
H43B	0.1209	0.7409	0.6635	0.107*
H43C	0.0825	0.5829	0.6097	0.107*
O51	0.0126 (2)	0.6793 (4)	0.27174 (19)	0.0653 (8)
O52	−0.1385 (3)	0.5437 (5)	0.3397 (3)	0.1090 (14)
C51	0.1083 (3)	0.5800 (6)	0.3180 (3)	0.0626 (11)
H51A	0.1251	0.4877	0.2786	0.075*
H51B	0.0801	0.5426	0.3791	0.075*
C52	−0.1077 (4)	0.6487 (6)	0.2894 (3)	0.0684 (12)
C53	−0.1945 (4)	0.7581 (8)	0.2382 (4)	0.0872 (15)
H53D	−0.2794	0.7320	0.2529	0.131*
H53A	−0.1845	0.7478	0.1707	0.131*
H53B	−0.1764	0.8660	0.2575	0.131*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0478 (12)	0.0564 (15)	0.0467 (13)	−0.0063 (11)	−0.0057 (10)	−0.0029 (13)
C1	0.0432 (17)	0.061 (2)	0.043 (2)	0.0059 (17)	−0.0027 (14)	0.0031 (18)
C2	0.0288 (14)	0.058 (2)	0.048 (2)	−0.0040 (15)	−0.0065 (13)	−0.0030 (17)
C3	0.0302 (14)	0.049 (2)	0.0439 (19)	0.0036 (14)	−0.0037 (13)	−0.0030 (16)
C4	0.0324 (14)	0.052 (2)	0.047 (2)	−0.0034 (14)	−0.0044 (13)	0.0009 (17)
C5	0.0421 (17)	0.051 (2)	0.050 (2)	−0.0020 (16)	−0.0076 (15)	0.0042 (17)
O2	0.0553 (14)	0.0623 (17)	0.0442 (14)	0.0045 (13)	0.0013 (11)	−0.0037 (13)
C6	0.0454 (18)	0.069 (3)	0.056 (2)	0.0075 (18)	−0.0018 (16)	−0.007 (2)
C7	0.0459 (18)	0.071 (3)	0.053 (2)	−0.0039 (19)	0.0065 (16)	−0.010 (2)
N1	0.0499 (16)	0.070 (2)	0.0474 (18)	−0.0045 (17)	−0.0018 (13)	−0.0030 (17)
C8	0.068 (3)	0.077 (3)	0.045 (2)	−0.003 (2)	0.0043 (19)	0.004 (2)
O8	0.091 (2)	0.081 (3)	0.098 (3)	0.000 (2)	−0.001 (2)	0.013 (2)
C9	0.051 (2)	0.109 (4)	0.045 (2)	−0.001 (2)	−0.0030 (17)	0.011 (3)
C10	0.059 (2)	0.106 (4)	0.055 (3)	−0.014 (3)	−0.0029 (19)	0.002 (3)
C11	0.059 (2)	0.087 (4)	0.061 (3)	−0.015 (3)	−0.001 (2)	−0.007 (3)
O11	0.083 (2)	0.076 (3)	0.129 (3)	−0.009 (2)	−0.015 (2)	−0.010 (2)
C12	0.073 (3)	0.151 (6)	0.065 (3)	0.017 (4)	−0.005 (2)	0.021 (4)
C13	0.054 (3)	0.226 (9)	0.063 (3)	0.004 (5)	−0.010 (2)	0.024 (5)
C14	0.071 (4)	0.213 (9)	0.076 (4)	−0.046 (5)	−0.015 (3)	0.022 (5)
C15	0.078 (3)	0.154 (6)	0.072 (3)	−0.043 (4)	−0.012 (3)	0.001 (4)
O21	0.0365 (11)	0.0660 (19)	0.0551 (15)	−0.0086 (12)	−0.0030 (10)	−0.0042 (14)
O22	0.085 (2)	0.086 (3)	0.166 (4)	−0.023 (2)	−0.040 (2)	0.050 (3)
C21	0.065 (3)	0.073 (3)	0.061 (2)	−0.028 (2)	0.001 (2)	0.002 (2)
C22	0.080 (3)	0.112 (4)	0.086 (3)	−0.051 (3)	0.006 (2)	−0.007 (3)
O31	0.0348 (10)	0.0560 (15)	0.0539 (15)	0.0015 (11)	−0.0042 (10)	−0.0070 (13)
O32	0.0583 (15)	0.087 (2)	0.084 (2)	0.0141 (17)	−0.0288 (14)	−0.0235 (19)
C31	0.0339 (16)	0.060 (2)	0.050 (2)	−0.0046 (16)	−0.0002 (14)	−0.0076 (18)
C32	0.047 (2)	0.067 (3)	0.088 (3)	−0.005 (2)	−0.0027 (19)	−0.016 (3)
O41	0.0408 (11)	0.0665 (17)	0.0460 (14)	0.0019 (12)	0.0017 (10)	0.0056 (13)
O42	0.0414 (14)	0.110 (3)	0.083 (2)	0.0099 (17)	0.0072 (14)	0.001 (2)
C42	0.0407 (18)	0.055 (2)	0.060 (2)	−0.0067 (17)	0.0022 (16)	−0.0098 (19)
C43	0.079 (3)	0.067 (3)	0.070 (3)	−0.010 (2)	0.024 (2)	0.001 (2)
O51	0.0504 (14)	0.077 (2)	0.0671 (17)	−0.0206 (14)	−0.0168 (12)	0.0149 (16)
O52	0.075 (2)	0.095 (3)	0.158 (4)	−0.015 (2)	0.020 (2)	0.042 (3)
C51	0.063 (2)	0.062 (3)	0.061 (3)	−0.017 (2)	−0.0092 (19)	0.006 (2)
C52	0.057 (2)	0.068 (3)	0.080 (3)	−0.015 (2)	−0.005 (2)	−0.004 (3)
C53	0.063 (3)	0.106 (4)	0.091 (3)	−0.006 (3)	−0.020 (2)	0.000 (3)

Geometric parameters (Å, º) top

O1—C5	1.428 (4)	C12—H12A	0.9300
O1—C1	1.427 (4)	C13—C14	1.363 (12)
C1—O2	1.384 (4)	C13—H13A	0.9300
C1—C2	1.508 (5)	C14—C15	1.374 (10)
C1—H1A	0.9800	C14—H14A	0.9300
C2—O21	1.433 (4)	C15—H15A	0.9300
C2—C3	1.515 (5)	O21—C21	1.357 (6)
C2—H2A	0.9800	O22—C21	1.179 (5)
C3—O31	1.441 (4)	C21—C22	1.490 (6)
C3—C4	1.511 (4)	C22—H22A	0.9600
C3—H3A	0.9800	C22—H22B	0.9600
C4—O41	1.440 (4)	C22—H22C	0.9600
C4—C5	1.516 (5)	O31—C31	1.362 (4)
C4—H4A	0.9800	O32—C31	1.186 (4)
C5—C51	1.510 (5)	C31—C32	1.478 (6)
C5—H5A	0.9800	C32—H32A	0.9600
O2—C6	1.436 (5)	C32—H32B	0.9600
C6—C7	1.506 (5)	C32—H32C	0.9600
C6—H6A	0.9700	O41—C42	1.357 (4)
C6—H6B	0.9700	O42—C42	1.184 (5)
C7—N1	1.443 (4)	C42—C43	1.486 (6)
C7—H7A	0.9700	C43—H43A	0.9600
C7—H7B	0.9700	C43—H43B	0.9600
N1—C11	1.387 (6)	C43—H43C	0.9600
N1—C8	1.392 (6)	O51—C52	1.338 (5)
C8—O8	1.198 (6)	O51—C51	1.448 (5)
C8—C9	1.485 (6)	O52—C52	1.181 (6)
C9—C10	1.368 (7)	C51—H51A	0.9700
C9—C12	1.376 (7)	C51—H51B	0.9700
C10—C15	1.387 (7)	C52—C53	1.467 (7)
C10—C11	1.492 (7)	C53—H53D	0.9600
C11—O11	1.208 (6)	C53—H53A	0.9600
C12—C13	1.414 (10)	C53—H53B	0.9600

C5—O1—C1	112.5 (2)	C9—C12—C13	116.2 (7)
O2—C1—O1	107.1 (3)	C9—C12—H12A	121.9
O2—C1—C2	109.5 (3)	C13—C12—H12A	121.9
O1—C1—C2	107.6 (3)	C14—C13—C12	122.4 (7)
O2—C1—H1A	110.8	C14—C13—H13A	118.8
O1—C1—H1A	110.8	C12—C13—H13A	118.8
C2—C1—H1A	110.8	C13—C14—C15	120.4 (7)
O21—C2—C1	109.6 (3)	C13—C14—H14A	119.8
O21—C2—C3	108.5 (3)	C15—C14—H14A	119.8
C1—C2—C3	110.8 (3)	C14—C15—C10	117.8 (8)
O21—C2—H2A	109.3	C14—C15—H15A	121.1
C1—C2—H2A	109.3	C10—C15—H15A	121.1
C3—C2—H2A	109.3	C21—O21—C2	118.3 (3)
O31—C3—C4	108.2 (2)	O22—C21—O21	123.3 (4)
O31—C3—C2	107.3 (3)	O22—C21—C22	125.9 (5)
C4—C3—C2	110.6 (3)	O21—C21—C22	110.7 (4)
O31—C3—H3A	110.2	C21—C22—H22A	109.5
C4—C3—H3A	110.2	C21—C22—H22B	109.5
C2—C3—H3A	110.2	H22A—C22—H22B	109.5
O41—C4—C3	109.0 (2)	C21—C22—H22C	109.5
O41—C4—C5	107.2 (3)	H22A—C22—H22C	109.5
C3—C4—C5	111.6 (3)	H22B—C22—H22C	109.5
O41—C4—H4A	109.7	C31—O31—C3	118.9 (3)
C3—C4—H4A	109.7	O32—C31—O31	123.7 (4)
C5—C4—H4A	109.7	O32—C31—C32	126.5 (4)
O1—C5—C51	107.0 (3)	O31—C31—C32	109.9 (3)
O1—C5—C4	110.0 (3)	C31—C32—H32A	109.5
C51—C5—C4	113.1 (3)	C31—C32—H32B	109.5
O1—C5—H5A	108.9	H32A—C32—H32B	109.5
C51—C5—H5A	108.9	C31—C32—H32C	109.5
C4—C5—H5A	108.9	H32A—C32—H32C	109.5
C1—O2—C6	113.1 (3)	H32B—C32—H32C	109.5
O2—C6—C7	108.6 (3)	C42—O41—C4	117.8 (3)
O2—C6—H6A	110.0	O42—C42—O41	122.8 (4)
C7—C6—H6A	110.0	O42—C42—C43	125.6 (4)
O2—C6—H6B	110.0	O41—C42—C43	111.6 (3)
C7—C6—H6B	110.0	C42—C43—H43A	109.5
H6A—C6—H6B	108.4	C42—C43—H43B	109.5
N1—C7—C6	112.6 (3)	H43A—C43—H43B	109.5
N1—C7—H7A	109.1	C42—C43—H43C	109.5
C6—C7—H7A	109.1	H43A—C43—H43C	109.5
N1—C7—H7B	109.1	H43B—C43—H43C	109.5
C6—C7—H7B	109.1	C52—O51—C51	118.0 (3)
H7A—C7—H7B	107.8	O51—C51—C5	108.1 (3)
C11—N1—C8	111.9 (4)	O51—C51—H51A	110.1
C11—N1—C7	123.8 (4)	C5—C51—H51A	110.1
C8—N1—C7	124.3 (4)	O51—C51—H51B	110.1
O8—C8—N1	125.6 (4)	C5—C51—H51B	110.1
O8—C8—C9	128.5 (5)	H51A—C51—H51B	108.4
N1—C8—C9	105.9 (4)	O52—C52—O51	122.9 (5)
C10—C9—C12	121.2 (5)	O52—C52—C53	124.8 (4)
C10—C9—C8	108.1 (4)	O51—C52—C53	112.3 (4)
C12—C9—C8	130.7 (6)	C52—C53—H53D	109.5
C9—C10—C15	122.0 (5)	C52—C53—H53A	109.5
C9—C10—C11	108.5 (4)	H53D—C53—H53A	109.5
C15—C10—C11	129.5 (6)	C52—C53—H53B	109.5
O11—C11—N1	125.0 (4)	H53D—C53—H53B	109.5
O11—C11—C10	129.5 (5)	H53A—C53—H53B	109.5
N1—C11—C10	105.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32B···O42ⁱ	0.96	2.45	3.317 (5)	151
C43—H43C···O42ⁱⁱ	0.96	2.48	3.284 (5)	141

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₇NO₁₂
M_r	521.47
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	10.6447 (8), 8.3655 (8), 14.0123 (13)
β (°)	92.263 (2)
V (Å³)	1246.80 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.34 × 0.22 × 0.20

Data collection
Diffractometer	Bruker APEX
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.77, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections	15243, 3092, 2238
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.132, 1.07
No. of reflections	3092
No. of parameters	334
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.14

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32B···O42ⁱ	0.96	2.45	3.317 (5)	151
C43—H43C···O42ⁱⁱ	0.96	2.48	3.284 (5)	141

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

Acknowledgements

We thank Dr P. Quagliotto for supplying crystals of the title compound.

References

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