1-Dibenzylamino-1-de­oxy-4,5-O-isopropyl­idene-β-d-fructopyran­ose

Huo, S.; Li, Y.; Liang, C.; Liu, J.; Zhao, W.

doi:10.1107/S1600536810053973

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o387

doi:10.1107/S1600536810053973

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1-Dibenzylamino-1-deoxy-4,5-O-isopropylidene-β-D-fructopyranose

Shiyong Huo,^a Yueqing Li,^a Chaoyan Liang,^a Jihong Liu ^a and Weijie Zhao ^a ^*

^aSchool of Pharmaceutical Science and Technology, Dalian University of Technology, No. 2 Linggong Road, Ganjingzi District, Dalian 116024, People's Republic of China
^*Correspondence e-mail: zyzhao@dlut.edu.cn

(Received 8 November 2010; accepted 24 December 2010; online 15 January 2011)

The title compound C₂₃H₂₉NO₅, synthesized by the Amadori rearrangement of α-D-glucose with dibenzylamine and the ketalization, is shown to be a β-anomer. The fructopyranose ring adopts a chair conformation. The two benzene rings form a dihedral angle of 68.9 (1)°. In the crystal, non–classical intermolecular C—H⋯O hydrogen bonds link the molecules into a three–dimensional network.

Related literature

For details of the synthesis of the title compound and the related ketone catalyst for asymmetric epoxidation, see: Shu et al. (2003 ); Tian et al. (2000 , 2002 ).

Experimental

Crystal data

C₂₃H₂₉NO₅
M_r = 399.47
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.328 (3) Å
b = 15.635 (5) Å
c = 16.547 (5) Å
V = 2154.6 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.32 × 0.26 × 0.18 mm

Data collection

Bruker SMART APEX CCD diffractometer
8591 measured reflections
3746 independent reflections
3078 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.099
S = 0.99
3746 reflections
264 parameters
12 restraints
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
C16—H16A⋯O5ⁱ	0.93	2.57	3.389 (3)	147
C17—H17A⋯O2ⁱⁱ	0.93	2.70	3.614 (3)	170
C19—H19A⋯O1ⁱⁱⁱ	0.93	2.59	3.428 (3)	150
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y, z-{\script{1\over 2}}]$ ; (iii) x+1, y, z.

Data collection: SMART (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810053973/rk2247sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810053973/rk2247Isup2.hkl

checkCIF report

Comment top

Asymmetric epoxidation of olefins presents a powerful strategy for the synthesis of enriched epoxides. The title compound is a key intermediate for the preparation of an effective epoxidation catalyst which provides encouragingly high enantiomeric excess value for the epoxidation of cis–olefins and styrenes (Shu et al., 2003; Tian et al., 2000, 2002). Furthermore, it can be another starting material to synthesize the corresponding amino sugar derivatives.

The title compound is prepared via two steps including Amadori rearrangement and ketalization (Fig. 1). In the molecular structure of the title compound (Fig. 2), the fructopyranose ring adopts a chair conformation - torsion angles: C3–C2–C1–O1 = 37.9 (3)° and C4–C3–C2–C1 = -32.9 (3)°. The structure is stabilized by the non–classical intermolecular hydrogen bonds (Table 1, Fig. 3).

Related literature top

For details of the synthesis of the title compound and the related ketone catalyst for asymmetric epoxidation, see: Shu et al. (2003); Tian et al. (2000, 2002).

Experimental top

The synthesis of the title compound was shown in Fig. 1. The pure title compound was first obtained by chromatography. It (10 g) was recrystallized from a solution of ethyl ether (50 ml) cooling at 255 K to afford colourless crystals.

The molecule is characterized by NMR (Fig. 4). ¹H NMR (400 MHz, CDCl₃): δ 7.25–7.35 (10H, m, Ar–H), 4.15–4.18 (2H, m, H–5, H–6e), 3.99–4.07 (3H, m, H–1'', H–1''', H–4), 3.91 (1H, d, J = 13.2 Hz, H–6a), 3.48 (2H, d, J = 13.2 Hz, H–1'', H–1'''), 3.29 (1H, d, J = 7.2 Hz, H–3), 3.07 (1H, d, J = 13.2 Hz, H–1), 2.69 (1H, d, J = 13.2 Hz, H–1), 1.51 (3H, s, H–3'), 1.34 (3H, s, H–1').

¹³C NMR (101 MHz, CDCl₃): δ 138.29 (C–2'', C–2'''), 129.31 (C–3'', C–7'', C–3''', C–7'''), 128.52 (C–4'', C–6'', C–4''', C–6'''), 127.46 (C–5'', C–5'''), 109.10 (C–2'), 96.21 (C–2), 77.79 (C–4), 73.68 (C–5), 72.17 (C–3), 59.18 (C–1'', C–1'''), 58.93 (C–6), 56.31 (C–1), 28.20 (C–1'), 26.28 (H–3').

HRMS(ES⁺): m/z [M+Cl]^- calcd. for C₂₃H₂₉NO₅Cl: 434.1734; found: 434.1737.

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The synthesis path of title compound.
	Fig. 2. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 3. A view of the packing of title compound. Dashed lines indicate non–classical C—H···O hydrogen bonds.
	Fig. 4. The structure of title compound, with atoms labeling corresponding to the characterization by NMR.

1-Dibenzylamino-1-deoxy-4,5-O-isopropylidene-β-D-fructopyranose top

Crystal data top

C₂₃H₂₉NO₅	D_x = 1.232 Mg m⁻³
M_r = 399.47	Melting point: 363 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2101 reflections
a = 8.328 (3) Å	θ = 2.5–22.9°
b = 15.635 (5) Å	µ = 0.09 mm⁻¹
c = 16.547 (5) Å	T = 293 K
V = 2154.6 (12) Å³	Block, colourless
Z = 4	0.32 × 0.26 × 0.18 mm
F(000) = 856

Data collection top

Bruker SMART APEX CCD diffractometer	3078 reflections with I > 2σ(I)
Radiation source: fine–focus sealed tube	R_int = 0.029
Graphite monochromator	θ_max = 25.0°, θ_min = 2.5°
ϕ– and ω–scans	h = −9→9
8591 measured reflections	k = −12→18
3746 independent reflections	l = −19→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.0586P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
3746 reflections	Δρ_max = 0.16 e Å⁻³
264 parameters	Δρ_min = −0.14 e Å⁻³
12 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0109 (15)

Crystal data top

C₂₃H₂₉NO₅	V = 2154.6 (12) Å³
M_r = 399.47	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.328 (3) Å	µ = 0.09 mm⁻¹
b = 15.635 (5) Å	T = 293 K
c = 16.547 (5) Å	0.32 × 0.26 × 0.18 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3078 reflections with I > 2σ(I)
8591 measured reflections	R_int = 0.029
3746 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	12 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 0.99	Δρ_max = 0.16 e Å⁻³
3746 reflections	Δρ_min = −0.14 e Å⁻³
264 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
N1	0.45371 (19)	−0.03531 (9)	−0.03276 (9)	0.0445 (4)
O1	0.26735 (16)	0.12669 (8)	0.01447 (7)	0.0462 (3)
O2	0.44619 (18)	0.05470 (9)	0.09987 (8)	0.0570 (4)
H2A	0.5176	0.0562	0.0658	0.086*
O3	0.1840 (3)	−0.02563 (10)	0.17613 (11)	0.0803 (5)
H3	0.2784	−0.0405	0.1776	0.120*
O4	0.03036 (19)	0.23207 (9)	0.11486 (7)	0.0552 (4)
O5	0.02593 (19)	0.14018 (9)	0.22165 (8)	0.0597 (4)
C1	0.2928 (3)	0.20454 (12)	0.05737 (11)	0.0531 (5)
H1A	0.2674	0.2522	0.0221	0.064*
H1B	0.4054	0.2088	0.0718	0.064*
C2	0.1933 (3)	0.21137 (12)	0.13278 (11)	0.0496 (5)
H2B	0.2389	0.2553	0.1682	0.059*
C3	0.1735 (3)	0.12850 (13)	0.17977 (11)	0.0488 (5)
H3B	0.2610	0.1232	0.2190	0.059*
C4	0.1688 (3)	0.04895 (12)	0.12720 (11)	0.0494 (5)
H4A	0.0637	0.0469	0.1007	0.059*
C5	0.2971 (2)	0.05151 (12)	0.06144 (10)	0.0430 (4)
C6	0.2938 (2)	−0.02364 (12)	0.00288 (11)	0.0468 (5)
H6A	0.2621	−0.0752	0.0313	0.056*
H6B	0.2159	−0.0129	−0.0395	0.056*
C7	0.4851 (3)	−0.12466 (12)	−0.05526 (12)	0.0552 (5)
H7A	0.5860	−0.1272	−0.0844	0.066*
H7B	0.4012	−0.1435	−0.0918	0.066*
C8	0.4931 (3)	−0.18588 (12)	0.01473 (13)	0.0530 (5)
C9	0.5592 (4)	−0.16474 (16)	0.08772 (15)	0.0766 (7)
H9A	0.5991	−0.1098	0.0956	0.092*
C10	0.5678 (4)	−0.2241 (2)	0.15046 (17)	0.0973 (10)
H10A	0.6114	−0.2084	0.2000	0.117*
C11	0.5121 (4)	−0.30535 (19)	0.1390 (2)	0.0940 (10)
H11A	0.5185	−0.3452	0.1806	0.113*
C12	0.4479 (4)	−0.32744 (19)	0.0676 (3)	0.0989 (10)
H12A	0.4106	−0.3829	0.0598	0.119*
C13	0.4368 (3)	−0.26813 (14)	0.00508 (19)	0.0782 (7)
H13A	0.3909	−0.2842	−0.0438	0.094*
C14	0.4789 (2)	0.02062 (13)	−0.10350 (11)	0.0487 (5)
H14A	0.4304	0.0759	−0.0929	0.058*
H14B	0.4248	−0.0041	−0.1499	0.058*
C15	0.6535 (2)	0.03325 (11)	−0.12364 (10)	0.0422 (4)
C16	0.7148 (3)	0.01268 (14)	−0.19830 (12)	0.0573 (5)
H16A	0.6475	−0.0112	−0.2371	0.069*
C17	0.8741 (3)	0.02674 (16)	−0.21685 (14)	0.0697 (7)
H17A	0.9137	0.0117	−0.2674	0.084*
C18	0.9742 (3)	0.06300 (15)	−0.16054 (15)	0.0674 (6)
H18A	1.0814	0.0729	−0.1731	0.081*
C19	0.9159 (3)	0.08463 (14)	−0.08581 (15)	0.0604 (6)
H19A	0.9832	0.1094	−0.0476	0.072*
C20	0.7577 (3)	0.06950 (12)	−0.06777 (12)	0.0525 (5)
H20A	0.7192	0.0839	−0.0168	0.063*
C21	−0.0606 (3)	0.21023 (14)	0.18498 (12)	0.0547 (5)
C22	−0.0670 (4)	0.28284 (16)	0.24500 (15)	0.0808 (8)
H22A	0.0402	0.2995	0.2592	0.121*
H22B	−0.1232	0.2646	0.2926	0.121*
H22C	−0.1221	0.3306	0.2213	0.121*
C23	−0.2231 (3)	0.1807 (2)	0.15849 (16)	0.0861 (8)
H23A	−0.2117	0.1346	0.1207	0.129*
H23B	−0.2791	0.2273	0.1332	0.129*
H23C	−0.2829	0.1614	0.2046	0.129*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0465 (10)	0.0434 (8)	0.0437 (8)	0.0012 (7)	0.0014 (7)	0.0021 (7)
O1	0.0531 (8)	0.0446 (7)	0.0408 (6)	−0.0049 (6)	0.0027 (6)	0.0049 (6)
O2	0.0469 (8)	0.0727 (9)	0.0514 (7)	−0.0011 (7)	−0.0076 (6)	0.0009 (7)
O3	0.1109 (15)	0.0558 (9)	0.0741 (10)	0.0149 (9)	0.0334 (11)	0.0294 (8)
O4	0.0653 (10)	0.0561 (8)	0.0442 (7)	0.0055 (7)	0.0080 (7)	0.0095 (6)
O5	0.0731 (10)	0.0584 (9)	0.0475 (7)	0.0065 (8)	0.0185 (7)	0.0122 (7)
C1	0.0606 (14)	0.0458 (10)	0.0528 (11)	−0.0090 (9)	0.0062 (10)	0.0019 (9)
C2	0.0558 (14)	0.0499 (11)	0.0430 (10)	−0.0093 (9)	0.0012 (10)	−0.0005 (9)
C3	0.0522 (12)	0.0571 (11)	0.0370 (9)	−0.0009 (10)	0.0017 (9)	0.0052 (9)
C4	0.0547 (13)	0.0472 (10)	0.0463 (10)	0.0015 (9)	0.0048 (10)	0.0144 (9)
C5	0.0411 (11)	0.0450 (9)	0.0431 (9)	−0.0026 (8)	−0.0022 (8)	0.0054 (8)
C6	0.0438 (12)	0.0464 (10)	0.0501 (10)	−0.0039 (8)	−0.0001 (9)	0.0051 (9)
C7	0.0651 (14)	0.0494 (11)	0.0511 (10)	0.0006 (10)	0.0012 (10)	−0.0058 (9)
C8	0.0459 (12)	0.0477 (11)	0.0655 (13)	0.0076 (9)	0.0075 (10)	0.0001 (10)
C9	0.105 (2)	0.0565 (13)	0.0679 (14)	0.0125 (14)	−0.0144 (15)	0.0049 (12)
C10	0.129 (3)	0.090 (2)	0.0731 (16)	0.0303 (19)	−0.0086 (17)	0.0177 (16)
C11	0.093 (2)	0.0794 (19)	0.110 (2)	0.0139 (16)	0.014 (2)	0.0413 (18)
C12	0.080 (2)	0.0638 (16)	0.153 (3)	−0.0102 (15)	0.000 (2)	0.0341 (19)
C13	0.0732 (17)	0.0566 (14)	0.1049 (19)	−0.0096 (12)	−0.0098 (15)	0.0108 (14)
C14	0.0523 (13)	0.0525 (10)	0.0413 (9)	−0.0004 (10)	−0.0045 (9)	0.0049 (9)
C15	0.0498 (12)	0.0368 (9)	0.0400 (9)	0.0008 (8)	−0.0027 (9)	0.0020 (8)
C16	0.0625 (15)	0.0628 (12)	0.0466 (11)	−0.0070 (11)	0.0016 (10)	−0.0054 (10)
C17	0.0740 (17)	0.0777 (16)	0.0575 (12)	−0.0052 (13)	0.0190 (12)	−0.0024 (13)
C18	0.0500 (14)	0.0664 (14)	0.0857 (16)	0.0005 (11)	0.0078 (13)	0.0138 (13)
C19	0.0523 (14)	0.0537 (12)	0.0752 (15)	−0.0066 (10)	−0.0172 (12)	0.0066 (11)
C20	0.0599 (14)	0.0515 (11)	0.0461 (10)	0.0015 (10)	−0.0060 (10)	−0.0040 (9)
C21	0.0632 (14)	0.0564 (11)	0.0444 (10)	0.0050 (10)	0.0082 (10)	0.0064 (9)
C22	0.112 (2)	0.0641 (14)	0.0663 (14)	0.0090 (15)	0.0213 (16)	−0.0049 (13)
C23	0.0639 (18)	0.123 (2)	0.0719 (15)	−0.0073 (16)	0.0027 (14)	0.0065 (16)

Geometric parameters (Å, º) top

N1—C6	1.468 (2)	C9—H9A	0.9300
N1—C7	1.469 (2)	C10—C11	1.366 (5)
N1—C14	1.476 (2)	C10—H10A	0.9300
O1—C1	1.425 (2)	C11—C12	1.343 (5)
O1—C5	1.431 (2)	C11—H11A	0.9300
O2—C5	1.396 (2)	C12—C13	1.392 (4)
O2—H2A	0.8200	C12—H12A	0.9300
O3—C4	1.425 (2)	C13—H13A	0.9300
O3—H3	0.8200	C14—C15	1.505 (3)
O4—C2	1.426 (3)	C14—H14A	0.9700
O4—C21	1.427 (2)	C14—H14B	0.9700
O5—C3	1.423 (3)	C15—C16	1.375 (3)
O5—C21	1.445 (2)	C15—C20	1.389 (3)
C1—C2	1.502 (3)	C16—C17	1.380 (3)
C1—H1A	0.9700	C16—H16A	0.9300
C1—H1B	0.9700	C17—C18	1.373 (3)
C2—C3	1.520 (3)	C17—H17A	0.9300
C2—H2B	0.9800	C18—C19	1.371 (3)
C3—C4	1.518 (3)	C18—H18A	0.9300
C3—H3B	0.9800	C19—C20	1.372 (3)
C4—C5	1.526 (3)	C19—H19A	0.9300
C4—H4A	0.9800	C20—H20A	0.9300
C5—C6	1.523 (3)	C21—C23	1.495 (4)
C6—H6A	0.9700	C21—C22	1.509 (3)
C6—H6B	0.9700	C22—H22A	0.9600
C7—C8	1.504 (3)	C22—H22B	0.9600
C7—H7A	0.9700	C22—H22C	0.9600
C7—H7B	0.9700	C23—H23A	0.9600
C8—C9	1.368 (3)	C23—H23B	0.9600
C8—C13	1.378 (3)	C23—H23C	0.9600
C9—C10	1.394 (4)

C6—N1—C7	112.42 (15)	C10—C9—H9A	119.4
C6—N1—C14	111.94 (15)	C11—C10—C9	119.9 (3)
C7—N1—C14	109.70 (15)	C11—C10—H10A	120.0
C1—O1—C5	113.91 (13)	C9—C10—H10A	120.0
C5—O2—H2A	109.5	C12—C11—C10	119.8 (3)
C4—O3—H3	109.5	C12—C11—H11A	120.1
C2—O4—C21	106.38 (15)	C10—C11—H11A	120.1
C3—O5—C21	108.89 (14)	C11—C12—C13	120.6 (3)
O1—C1—C2	113.12 (16)	C11—C12—H12A	119.7
O1—C1—H1A	109.0	C13—C12—H12A	119.7
C2—C1—H1A	109.0	C8—C13—C12	120.9 (3)
O1—C1—H1B	109.0	C8—C13—H13A	119.6
C2—C1—H1B	109.0	C12—C13—H13A	119.6
H1A—C1—H1B	107.8	N1—C14—C15	112.98 (15)
O4—C2—C1	111.62 (16)	N1—C14—H14A	109.0
O4—C2—C3	101.33 (16)	C15—C14—H14A	109.0
C1—C2—C3	115.10 (17)	N1—C14—H14B	109.0
O4—C2—H2B	109.5	C15—C14—H14B	109.0
C1—C2—H2B	109.5	H14A—C14—H14B	107.8
C3—C2—H2B	109.5	C16—C15—C20	117.5 (2)
O5—C3—C4	111.21 (17)	C16—C15—C14	121.80 (18)
O5—C3—C2	103.50 (16)	C20—C15—C14	120.65 (17)
C4—C3—C2	114.08 (14)	C15—C16—C17	121.3 (2)
O5—C3—H3B	109.3	C15—C16—H16A	119.3
C4—C3—H3B	109.3	C17—C16—H16A	119.3
C2—C3—H3B	109.3	C18—C17—C16	119.9 (2)
O3—C4—C3	110.03 (15)	C18—C17—H17A	120.0
O3—C4—C5	111.37 (16)	C16—C17—H17A	120.0
C3—C4—C5	111.65 (16)	C19—C18—C17	120.0 (2)
O3—C4—H4A	107.9	C19—C18—H18A	120.0
C3—C4—H4A	107.9	C17—C18—H18A	120.0
C5—C4—H4A	107.9	C18—C19—C20	119.6 (2)
O2—C5—O1	111.86 (14)	C18—C19—H19A	120.2
O2—C5—C6	109.49 (15)	C20—C19—H19A	120.2
O1—C5—C6	106.55 (13)	C19—C20—C15	121.7 (2)
O2—C5—C4	107.41 (15)	C19—C20—H20A	119.1
O1—C5—C4	106.71 (15)	C15—C20—H20A	119.1
C6—C5—C4	114.87 (16)	O4—C21—O5	104.94 (17)
N1—C6—C5	109.56 (15)	O4—C21—C23	108.43 (18)
N1—C6—H6A	109.8	O5—C21—C23	109.9 (2)
C5—C6—H6A	109.8	O4—C21—C22	111.94 (18)
N1—C6—H6B	109.8	O5—C21—C22	108.14 (18)
C5—C6—H6B	109.8	C23—C21—C22	113.1 (2)
H6A—C6—H6B	108.2	C21—C22—H22A	109.5
N1—C7—C8	114.70 (15)	C21—C22—H22B	109.5
N1—C7—H7A	108.6	H22A—C22—H22B	109.5
C8—C7—H7A	108.6	C21—C22—H22C	109.5
N1—C7—H7B	108.6	H22A—C22—H22C	109.5
C8—C7—H7B	108.6	H22B—C22—H22C	109.5
H7A—C7—H7B	107.6	C21—C23—H23A	109.5
C9—C8—C13	117.7 (2)	C21—C23—H23B	109.5
C9—C8—C7	122.96 (19)	H23A—C23—H23B	109.5
C13—C8—C7	119.3 (2)	C21—C23—H23C	109.5
C8—C9—C10	121.2 (3)	H23A—C23—H23C	109.5
C8—C9—H9A	119.4	H23B—C23—H23C	109.5

C3—C2—C1—O1	37.9 (3)	C4—C3—C2—C1	−32.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O5ⁱ	0.93	2.57	3.389 (3)	147
C17—H17A···O2ⁱⁱ	0.93	2.70	3.614 (3)	170
C19—H19A···O1ⁱⁱⁱ	0.93	2.59	3.428 (3)	150

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₉NO₅
M_r	399.47
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	8.328 (3), 15.635 (5), 16.547 (5)
V (Å³)	2154.6 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.26 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8591, 3746, 3078
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.099, 0.99
No. of reflections	3746
No. of parameters	264
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.14

Computer programs: SMART (Bruker, 2005), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O5ⁱ	0.93	2.57	3.389 (3)	147
C17—H17A···O2ⁱⁱ	0.93	2.70	3.614 (3)	170
C19—H19A···O1ⁱⁱⁱ	0.93	2.59	3.428 (3)	150

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

Acknowledgements

We thank Dr Yang Li for his help during the refinement.

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shu, L., Shen, Y.-M., Burke, C., Goeddel, D. & Shi, Y. (2003). J. Org. Chem. 68, 4963–4965. Web of Science CrossRef PubMed CAS Google Scholar
Tian, H., She, X., Yu, H., Shu, L. & Shi, Y. (2002). J. Org. Chem. 67, 2435–2446. Web of Science CSD CrossRef PubMed CAS Google Scholar
Tian, H., Shu, L., Yu, H. & Shi, Y. (2000). J. Am. Chem. Soc. 122, 11551–11552. Web of Science CrossRef CAS Google Scholar