2-Azido-3,4;6,7-di-O-isopropyl­idene-α-d-glycero-d-talo-heptopyran­ose

Jenkinson, S.F.; Lenagh-Snow, G.M.J.; Izumori, K.; Fleet, G.W.J.; Watkin, D.J.; Thompson, A.L.

doi:10.1107/S1600536810003995

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages o525-o526

doi:10.1107/S1600536810003995

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2-Azido-3,4;6,7-di-O-isopropylidene-α-D-glycero-D-talo-heptopyranose

Sarah F. Jenkinson,^a ^* Gabriel M. J. Lenagh-Snow,^a Ken Izumori,^b George W. J. Fleet,^a David J. Watkin ^c and Amber L. Thompson ^c

^aDepartment of Organic Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, England, ^bRare Sugar Research Centre, Kagawa University, 2393 Miki-cho, Kita-gun, Kagawa 761-0795, Japan, and ^cDepartment of Chemical Crystallography, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, England
^*Correspondence e-mail: sarah.jenkinson@chem.ox.ac.uk

(Received 28 January 2010; accepted 1 February 2010; online 6 February 2010)

In the title compound, C₁₃H₂₁N₃O₆, the six-membered ring adopts a twist-boat conformation with the azide group in the bowsprit position. The azide group is disordered over two sets of sites in a 0.642 (10):0.358 (10) ratio. The crystal structure consists of O—H⋯O hydrogen-bonded trimer units. The absolute configuration was determined from the use of D-mannose as the starting material.

Related literature

For Izumoring techniques, see: Izumori (2002 , 2006 ); Yoshihara et al. (2008 ); Gullapalli et al. (2010 ); Rao et al. (2008 , 2009 ); Jones et al. (2008 ); Jenkinson et al. (2009 ). For the synthesis of homonojirimycins, see: Compain et al. (2009 ); Asano (2009 ); Watson et al. (2001 ) and for their isolation, see: Ikeda et al. (2000 ); Asano et al. (1998 ); Kite et al. (1988 ). For the synthesis of the azidoheptitol, see: Beacham et al. (1991 ); Bruce et al. (1990 ); Myerscough et al. (1992 ). For the weighting scheme, see: Prince (1982 ); Watkin (1994 ).

Experimental

Crystal data

C₁₃H₂₁N₃O₆
M_r = 315.33
Trigonal, R 3
a = 16.8793 (2) Å
c = 15.1043 (3) Å
V = 3726.83 (10) Å³
Z = 9
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 150 K
0.70 × 0.50 × 0.30 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.63, T_max = 0.97
23870 measured reflections
1889 independent reflections
1770 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.070
S = 0.87
1889 reflections
227 parameters
43 restraints
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10—H101⋯O6ⁱ	0.84	1.93	2.761 (3)	171
Symmetry code: (i) -x+y+1, -x+1, z.

Data collection: COLLECT (Nonius, 2001 ); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: CAMERON (Watkin et al., 1996 ); software used to prepare material for publication: CRYSTALS.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003995/lh2989sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810003995/lh2989Isup2.hkl

checkCIF report

Comment top

The enzymatic interconversion of monosaccharides has been developed by Izumori (2002, 2006) and has been seen to be generally applicable for the 1-deoxy ketohexoses (Yoshihara et al., 2008, Gullapalli et al., 2010; Rao et al., 2009) and branched sugars (Rao et al., 2008; Jones et al., 2008). The methodology has also been applied to azido heptitols (Jenkinson et al., 2009) and thus to the synthesis of 2,6-dideoxy-2,6-iminoheptitols (homonojirimycins), seven carbon imino sugars (Compain et al., 2009; Asano et al., 2009; Watson et al., 2001) which are a family of glycosidase inhibitors. A number of homonojrimycins have been isolated as natural products from medicinal plants (Ikeda et al., 2000; Asano et al., 1998; Kite et al., 1988).

A Kiliani cyanide reaction on diacetone mannose gave the lactone diacetonide 1 (Beacham et al., 1991; Myerscough et al., 1992). Esterification of 1 (Fig. 1) with triflic anhydride in pyridine followed by reaction with sodium azide in DMF gave the azide 2 with retention of configuration at C2; the stereochemistry of 2 was established by X-ray crystallographic analysis (Bruce et al., 1990). Reduction of the lactone 2 afforded the lactol 3, a key intermediate for the synthesis of four of the possible sixteen iminoheptitols 4 by Izumoring techniques. The reported crystal structure of 3 determines the configuration of both the azide at C2 and the anomeric position.

The X-ray structure shows that the six-membered ring in the title compound adopts a twist boat conformation with the azide in the bowsprit position and the anomeric alcohol group in the less hindered α-position (Fig. 2). There is significant disorder in the structure with the azide occupying two possible sites. The compound exists as repeating hydrogen bonded trimer units (Fig.3, Fig. 4, Fig. 5). The absolute configuration was determined from the use of D-mannose as the starting material. Only classical hydrogen bonding was considered.

Related literature top

For Izumoring techniques, see: Izumori (2002, 2006); Yoshihara et al. (2008); Gullapalli et al. (2010); Rao et al. (2008, 2009); Jones et al. (2008); Jenkinson et al. (2009). For the synthesis of homonojirimycins, see: Compain et al. (2009); Asano et al. (2009); Watson et al. (2001) and for their isolation, see: Ikeda et al. (2000); Asano et al. (1998); Kite et al. (1988). For the synthesis of the azidoheptitol, see: Beacham et al. (1991); Bruce et al. (1990); Myerscough et al. (1992). For the weighting scheme, see: Prince (1982); Watkin (1994).

Experimental top

The title compound was recrystallised from diethyl ether: m.p. 397-398 K; [α]_D²⁵ +41.3 (c, 1.0 in CHCl₃) {Lit. (Myerscough et al., 1992) m.p. 387-388 K; [α]_D²⁰ +41.0 (c, 1.0 in CHCl₃).

Computing details top

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top

	Fig. 1. Synthetic Scheme
	Fig. 2. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.
	Fig. 3. Hydrogen bonded trimer unit. Hydrogen bonds are shown as dotted lines.
	Fig. 4. Packing diagram for the title compound projected along the c-axis. Hydrogen bonds are shown by dotted lines.
	Fig. 5. Packing diagram for the title compound projected along the b-axis. Hydrogen bonds are shown by dotted lines.

2-Azido-3,4;6,7-di-O-isopropylidene-α-D-glycero- D-talo-heptopyranose top

Crystal data top

C₁₃H₂₁N₃O₆	D_x = 1.264 Mg m⁻³
M_r = 315.33	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 1885 reflections
Hall symbol: R 3	θ = 5–28°
a = 16.8793 (2) Å	µ = 0.10 mm⁻¹
c = 15.1043 (3) Å	T = 150 K
V = 3726.83 (10) Å³	Plate, colourless
Z = 9	0.70 × 0.50 × 0.30 mm
F(000) = 1512

Data collection top

Nonius KappaCCD diffractometer	1770 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 27.5°, θ_min = 5.2°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −21→21
T_min = 0.63, T_max = 0.97	k = −21→21
23870 measured reflections	l = −19→19
1889 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.070	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A₀T₀(x) + A₁T₁(x) ··· + A_n-1]T_n-1(x)] where A_i are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] [1-(deltaF/6*sigmaF)²]² A_i are: 35.7 56.9 32.2 12.2 2.39
S = 0.87	(Δ/σ)_max = 0.000424
1889 reflections	Δρ_max = 0.16 e Å⁻³
227 parameters	Δρ_min = −0.16 e Å⁻³
43 restraints

Crystal data top

C₁₃H₂₁N₃O₆	Z = 9
M_r = 315.33	Mo Kα radiation
Trigonal, R3	µ = 0.10 mm⁻¹
a = 16.8793 (2) Å	T = 150 K
c = 15.1043 (3) Å	0.70 × 0.50 × 0.30 mm
V = 3726.83 (10) Å³

Data collection top

Nonius KappaCCD diffractometer	1889 independent reflections
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	1770 reflections with I > 2σ(I)
T_min = 0.63, T_max = 0.97	R_int = 0.034
23870 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	43 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 0.87	Δρ_max = 0.16 e Å⁻³
1889 reflections	Δρ_min = −0.16 e Å⁻³
227 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.73085 (8)	0.56052 (8)	0.60278 (11)	0.0388
C2	0.71163 (11)	0.63258 (11)	0.58727 (14)	0.0334
C3	0.60997 (11)	0.59051 (10)	0.56713 (13)	0.0348
O4	0.55748 (8)	0.55027 (8)	0.64559 (12)	0.0420
C5	0.49780 (12)	0.45418 (11)	0.63308 (14)	0.0398
O6	0.53523 (9)	0.43128 (8)	0.55852 (11)	0.0414
C7	0.57940 (12)	0.51014 (10)	0.50233 (14)	0.0370
C9	0.72913 (13)	0.51340 (12)	0.52439 (14)	0.0407
O10	0.81499 (10)	0.55590 (10)	0.48357 (13)	0.0511
C14	0.50399 (17)	0.40362 (15)	0.71240 (16)	0.0540
C15	0.40195 (14)	0.43489 (16)	0.61352 (17)	0.0544
C16	0.74277 (12)	0.69311 (12)	0.66864 (14)	0.0376
O17	0.72041 (8)	0.76403 (8)	0.65905 (12)	0.0420
C18	0.80336 (12)	0.84914 (11)	0.63848 (14)	0.0408
O19	0.87138 (8)	0.82461 (9)	0.62410 (12)	0.0457
C20	0.84636 (13)	0.74546 (14)	0.67731 (16)	0.0468
C21	0.79042 (17)	0.88864 (16)	0.55377 (18)	0.0588
C22	0.82716 (16)	0.91340 (13)	0.71627 (16)	0.0519
H21	0.7470	0.6687	0.5353	0.0391*
H31	0.5978	0.6378	0.5436	0.0413*
H71	0.5361	0.5093	0.4580	0.0446*
H91	0.7123	0.4508	0.5415	0.0490*
H141	0.4682	0.3379	0.7027	0.0810*
H142	0.4804	0.4199	0.7637	0.0803*
H143	0.5683	0.4214	0.7219	0.0805*
H152	0.3632	0.3698	0.6047	0.0812*
H153	0.3773	0.4541	0.6630	0.0797*
H151	0.4011	0.4664	0.5607	0.0801*
H161	0.7134	0.6569	0.7208	0.0440*
H201	0.8648	0.7629	0.7392	0.0552*
H202	0.8739	0.7101	0.6556	0.0567*
H212	0.8455	0.9466	0.5425	0.0887*
H213	0.7396	0.9001	0.5601	0.0886*
H211	0.7793	0.8473	0.5054	0.0875*
H222	0.8852	0.9682	0.7049	0.0781*
H223	0.8309	0.8835	0.7700	0.0772*
H221	0.7802	0.9302	0.7229	0.0777*
H101	0.8447	0.5336	0.5065	0.0762*
C80	0.66053 (13)	0.51225 (11)	0.45706 (13)	0.0399	0.642 (10)
N110	0.6365 (5)	0.4337 (5)	0.3965 (5)	0.0459	0.642 (10)
N120	0.6176 (3)	0.4422 (3)	0.3203 (3)	0.0485	0.642 (10)
N130	0.5963 (4)	0.4412 (3)	0.2497 (2)	0.0824	0.642 (10)
C81	0.66053 (13)	0.51225 (11)	0.45706 (13)	0.0399	0.358 (10)
N111	0.6151 (11)	0.4225 (12)	0.4122 (11)	0.0617	0.358 (10)
N121	0.6429 (6)	0.4295 (6)	0.3378 (7)	0.0510	0.358 (10)
N131	0.6661 (7)	0.4252 (6)	0.2652 (4)	0.0936	0.358 (10)
H801	0.6910	0.5680	0.4222	0.0469*	0.642 (10)
H811	0.6898	0.5645	0.4171	0.0473*	0.358 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0408 (6)	0.0341 (6)	0.0477 (7)	0.0235 (5)	−0.0023 (5)	0.0055 (5)
C2	0.0319 (7)	0.0255 (7)	0.0436 (8)	0.0150 (6)	−0.0009 (6)	0.0042 (6)
C3	0.0331 (8)	0.0254 (7)	0.0461 (9)	0.0149 (6)	−0.0014 (6)	0.0017 (6)
O4	0.0358 (6)	0.0264 (6)	0.0545 (7)	0.0084 (5)	0.0071 (5)	−0.0027 (5)
C5	0.0368 (8)	0.0246 (7)	0.0493 (9)	0.0088 (6)	−0.0017 (7)	−0.0007 (6)
O6	0.0444 (7)	0.0234 (5)	0.0493 (7)	0.0117 (5)	−0.0005 (5)	0.0004 (5)
C7	0.0401 (8)	0.0251 (7)	0.0449 (9)	0.0156 (6)	−0.0042 (7)	0.0014 (6)
C9	0.0454 (9)	0.0324 (8)	0.0518 (10)	0.0251 (7)	0.0036 (8)	0.0077 (7)
O10	0.0522 (8)	0.0543 (8)	0.0632 (8)	0.0390 (7)	0.0123 (7)	0.0181 (7)
C14	0.0670 (13)	0.0407 (10)	0.0523 (12)	0.0254 (10)	−0.0002 (10)	0.0048 (8)
C15	0.0359 (9)	0.0534 (12)	0.0609 (13)	0.0125 (9)	−0.0035 (9)	−0.0009 (9)
C16	0.0341 (8)	0.0311 (7)	0.0438 (9)	0.0133 (7)	−0.0011 (6)	0.0024 (6)
O17	0.0318 (6)	0.0271 (5)	0.0606 (8)	0.0100 (5)	0.0033 (5)	−0.0025 (5)
C18	0.0361 (8)	0.0287 (8)	0.0475 (9)	0.0086 (7)	0.0026 (7)	0.0017 (7)
O19	0.0317 (6)	0.0391 (7)	0.0562 (8)	0.0100 (5)	0.0028 (5)	0.0012 (6)
C20	0.0368 (9)	0.0405 (9)	0.0573 (11)	0.0150 (8)	−0.0072 (8)	−0.0021 (8)
C21	0.0641 (13)	0.0517 (12)	0.0538 (11)	0.0239 (11)	−0.0022 (10)	0.0072 (9)
C22	0.0556 (12)	0.0312 (9)	0.0533 (11)	0.0099 (8)	0.0038 (9)	−0.0034 (8)
C80	0.0489 (10)	0.0299 (8)	0.0448 (9)	0.0226 (7)	−0.0012 (7)	−0.0005 (6)
N110	0.064 (4)	0.033 (3)	0.043 (3)	0.026 (3)	0.004 (3)	−0.0027 (19)
N120	0.049 (2)	0.0377 (17)	0.049 (2)	0.0148 (14)	0.0016 (15)	−0.0079 (14)
N130	0.104 (4)	0.063 (2)	0.052 (2)	0.021 (2)	−0.0091 (19)	−0.0184 (15)
C81	0.0489 (10)	0.0299 (8)	0.0448 (9)	0.0226 (7)	−0.0012 (7)	−0.0005 (6)
N111	0.072 (7)	0.034 (4)	0.060 (6)	0.013 (4)	0.032 (4)	0.001 (3)
N121	0.053 (4)	0.045 (3)	0.052 (4)	0.022 (3)	0.000 (3)	0.002 (3)
N131	0.112 (7)	0.094 (6)	0.050 (4)	0.033 (5)	0.009 (4)	−0.010 (3)

Geometric parameters (Å, º) top

O1—C2	1.4261 (18)	C15—H152	0.966
O1—C9	1.419 (2)	C15—H153	0.985
C2—C3	1.524 (2)	C15—H151	0.963
C2—C16	1.515 (2)	C16—O17	1.431 (2)
C2—H21	0.991	C16—C20	1.520 (2)
C3—O4	1.431 (2)	C16—H161	0.968
C3—C7	1.538 (2)	O17—C18	1.452 (2)
C3—H31	0.986	C18—O19	1.419 (2)
O4—C5	1.4309 (19)	C18—C21	1.508 (3)
C5—O6	1.436 (2)	C18—C22	1.511 (3)
C5—C14	1.505 (3)	O19—C20	1.430 (2)
C5—C15	1.511 (3)	C20—H201	0.983
O6—C7	1.434 (2)	C20—H202	0.978
C7—H71	0.986	C21—H212	0.971
C7—C80	1.515 (3)	C21—H213	0.974
C7—H71	0.986	C21—H211	0.962
C7—C81	1.515 (3)	C22—H222	0.969
C9—O10	1.398 (2)	C22—H223	0.974
C9—H91	0.982	C22—H221	0.971
C9—C80	1.534 (3)	C80—N110	1.491 (8)
C9—O10	1.398 (2)	C80—H801	0.971
C9—H91	0.982	N110—N120	1.221 (8)
C9—C81	1.534 (3)	N120—N130	1.123 (6)
O10—H101	0.838	C81—N111	1.477 (19)
C14—H141	0.974	C81—H811	0.975
C14—H142	0.971	N111—N121	1.201 (16)
C14—H143	0.982	N121—N131	1.179 (13)

C2—O1—C9	113.04 (12)	C5—C15—H153	111.3
O1—C2—C3	108.58 (13)	H152—C15—H153	108.8
O1—C2—C16	106.97 (13)	C5—C15—H151	110.7
C3—C2—C16	113.98 (14)	H152—C15—H151	108.9
O1—C2—H21	109.4	H153—C15—H151	108.8
C3—C2—H21	108.7	C2—C16—O17	109.54 (13)
C16—C2—H21	109.2	C2—C16—C20	111.86 (16)
C2—C3—O4	109.97 (14)	O17—C16—C20	103.32 (14)
C2—C3—C7	109.94 (14)	C2—C16—H161	109.8
O4—C3—C7	104.67 (12)	O17—C16—H161	110.2
C2—C3—H31	109.7	C20—C16—H161	111.9
O4—C3—H31	110.6	C16—O17—C18	108.78 (13)
C7—C3—H31	111.8	O17—C18—O19	105.35 (14)
C3—O4—C5	110.27 (13)	O17—C18—C21	109.73 (16)
O4—C5—O6	104.70 (14)	O19—C18—C21	108.44 (17)
O4—C5—C14	109.19 (15)	O17—C18—C22	108.82 (15)
O6—C5—C14	107.89 (15)	O19—C18—C22	111.41 (16)
O4—C5—C15	109.94 (15)	C21—C18—C22	112.81 (17)
O6—C5—C15	110.88 (16)	C18—O19—C20	106.42 (14)
C14—C5—C15	113.82 (17)	C16—C20—O19	102.19 (15)
C5—O6—C7	107.99 (12)	C16—C20—H201	110.8
C3—C7—O6	103.40 (13)	O19—C20—H201	110.7
C3—C7—H71	111.3	C16—C20—H202	112.1
O6—C7—H71	110.5	O19—C20—H202	111.9
C3—C7—C80	111.47 (14)	H201—C20—H202	109.0
O6—C7—C80	109.47 (13)	C18—C21—H212	108.5
H71—C7—C80	110.5	C18—C21—H213	109.9
C3—C7—O6	103.40 (13)	H212—C21—H213	108.2
C3—C7—H71	111.3	C18—C21—H211	110.0
O6—C7—H71	110.5	H212—C21—H211	109.8
C3—C7—C81	111.47 (14)	H213—C21—H211	110.3
O6—C7—C81	109.47 (13)	C18—C22—H222	109.1
H71—C7—C81	110.5	C18—C22—H223	109.8
O1—C9—O10	110.79 (15)	H222—C22—H223	110.3
O1—C9—H91	107.3	C18—C22—H221	109.1
O10—C9—H91	109.7	H222—C22—H221	108.8
O1—C9—C80	111.36 (13)	H223—C22—H221	109.8
O10—C9—C80	107.23 (15)	C9—C80—C7	111.64 (15)
H91—C9—C80	110.5	C9—C80—N110	106.6 (3)
O1—C9—O10	110.79 (15)	C7—C80—N110	114.6 (3)
O1—C9—H91	107.3	C9—C80—H801	108.4
O10—C9—H91	109.7	C7—C80—H801	107.6
O1—C9—C81	111.36 (13)	N110—C80—H801	107.8
O10—C9—C81	107.23 (15)	C80—N110—N120	116.4 (6)
H91—C9—C81	110.5	N110—N120—N130	173.3 (6)
C9—O10—H101	106.7	C9—C81—C7	111.64 (15)
C5—C14—H141	110.3	C9—C81—N111	108.6 (8)
C5—C14—H142	108.7	C7—C81—N111	100.5 (5)
H141—C14—H142	109.5	C9—C81—H811	111.2
C5—C14—H143	108.9	C7—C81—H811	110.2
H141—C14—H143	109.4	N111—C81—H811	114.3
H142—C14—H143	110.1	C81—N111—N121	110.6 (11)
C5—C15—H152	108.4	N111—N121—N131	172.0 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H153···O10ⁱ	0.99	2.51	3.361 (3)	145
O10—H101···O6ⁱⁱ	0.84	1.93	2.761 (3)	171
C80—H801···O4ⁱⁱⁱ	0.97	2.36	3.296 (3)	161
C81—H801···O4ⁱⁱⁱ	0.97	2.36	3.296 (3)	161
C80—H811···O4ⁱⁱⁱ	0.97	2.34	3.296 (3)	166
C81—H811···O4ⁱⁱⁱ	0.97	2.34	3.296 (3)	166

Symmetry codes: (i) −x+y+2/3, −x+4/3, z+1/3; (ii) −x+y+1, −x+1, z; (iii) −y+4/3, x−y+2/3, z−1/3.

Experimental details

Crystal data
Chemical formula	C₁₃H₂₁N₃O₆
M_r	315.33
Crystal system, space group	Trigonal, R3
Temperature (K)	150
a, c (Å)	16.8793 (2), 15.1043 (3)
V (Å³)	3726.83 (10)
Z	9
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.70 × 0.50 × 0.30

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.63, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	23870, 1889, 1770
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.070, 0.87
No. of reflections	1889
No. of parameters	227
No. of restraints	43
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.16

Computer programs: COLLECT (Nonius, 2001), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10—H101···O6ⁱ	0.84	1.93	2.761 (3)	171

Symmetry code: (i) −x+y+1, −x+1, z.

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Volume 66| Part 3| March 2010| Pages o525-o526

doi:10.1107/S1600536810003995

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