Methyl (2′R,3′R)-2-azido-2,6-di­deoxy-3,4-O-(2′,3′-di­methoxy­butane-2′,3′-diyl)-α-l-gluco­pyran­oside

Barnes, J.C.; Brimacombe, J.S.; Connolly, L.M.C.; Dix, A.P.

doi:10.1107/S1600536802001940

Methyl (2′R,3′R)-2-azido-2,6-dideoxy-3,4-O-(2′,3′-dimethoxybutane-2′,3′-diyl)-α-L-glucopyranoside

J. C. Barnes, J. S. Brimacombe, L. M. C. Connolly and A. P. Dix

Unlike other α-mannopyranoside-2-sulphonates, the 2-O-trifluoromethylsulfonyl (trifluoromethanesulfonate) derivative, (II), underwent an S_N2 displacement with an azide ion to give methyl (2′R,3′R)-2-azido-2,6-dideoxy-3,4-O-(2′,3′-dimethoxybutane-2′,3′-diyl)-α-L-glucopyranoside, C₁₃H₂₃N₃O₆, (IV), in preference to the E2 reaction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001940/dn6016sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001940/dn6016Isup2.hkl Contains datablock I

CCDC reference: 182598

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.006 Å
R factor = 0.032
wR factor = 0.058
Data-to-parameter ratio = 7.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           24.97
         From the CIF: _reflns_number_total               2861
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         3243
         Completeness (_total/calc)             88.22%
          Alert B: < 90% complete (theta max?)


 Alert Level C:



GOODF_01  Alert C The least squares goodness of fit parameter lies
          outside the range 0.80 <> 2.00
          Goodness of fit given =      0.723

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           24.97
         From the CIF: _reflns_number_total               2861
         From the CIF: _diffrn_reflns_limit_ max hkl   10.   11.   30.
         From the CIF: _diffrn_reflns_limit_ min hkl  -10.   -9.  -34.
         TEST1: Expected hkl limits for theta max
         Calculated maximum hkl   11.   12.   36.
         Calculated minimum hkl  -11.  -12.  -36.
          ALERT: Expected hkl max differ from CIF values

REFLT_03
         From the CIF: _diffrn_reflns_theta_max           24.97
         From the CIF: _reflns_number_total               2861
         Count of symmetry unique reflns         3243
         Completeness (_total/calc)             88.22%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

There are two, essentially identical, independent molecules in the asymmetric unit of the title compound, (IV). The structure of one of these molecules is shown in Fig. 1. There are no unusual bond lengths or angles. Comparison with the structure of (III) (Barnes et al., 2002) shows that the original conformation is preserved at all centers except for inversion of the configuration at the reaction centre C2. In the absence of a heavy atom, the absolute conformation of (IV) could not be determined but the alternate assumption that the entire conformation had reversed apart from C2 is untenable.

Experimental top

(II) and (IV) were prepared as described for the D-enantiomers (Dix et al., 2001) Analysis of (IV), found: C 49.34, H 7.59, N 13.18%; calculated: C 49.20, H 7.31, N 13.24%. [α]_D -291° (cl, CHCl₃). Crystals from ethyl acetate/hexane.

Computing details top

Data collection: MADNES (Pflugrath & Messerschmidt, 1990); cell refinement: MADNES; data reduction: MADNES; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON92 (Spek, 1992) and PLATON92 (Spek, 1992); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The structure of one of the independent molecules of (IV), showing 50% probability displacement ellipsoids.

(2'R,3'R)-methyl 2-azido-2,6-dideoxy-3,4-O-(2',3'-dimethoxybutane- 2',3'-diyl)-α-L-glucopyranoside. top

Crystal data top

C₁₃H₂₃N₃O₆	D_x = 1.298 Mg m⁻³
M_r = 317.34	Melting point = 88–89 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 250 reflections
a = 10.065 (4) Å	θ = 2.1–25.0°
b = 10.512 (16) Å	µ = 0.10 mm⁻¹
c = 30.696 (10) Å	T = 150 K
V = 3248 (5) Å³	Block, colourless
Z = 8	0.32 × 0.18 × 0.10 mm
F(000) = 1360

Data collection top

Enraf-Nonius FAST system diffractometer	1724 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR591 rotating anode	R_int = 0.073
Graphite monochromator	θ_max = 25.0°, θ_min = 2.1°
see exptl_special_details scans	h = −10→10
11775 measured reflections	k = −9→11
2861 independent reflections	l = −34→30

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.058	H-atom parameters constrained
S = 0.72	w = 1/[σ²(F_o²) + (0.0051P)²] where P = (F_o² + 2F_c²)/3
2861 reflections	(Δ/σ)_max = 0.027
409 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₃H₂₃N₃O₆	V = 3248 (5) Å³
M_r = 317.34	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.065 (4) Å	µ = 0.10 mm⁻¹
b = 10.512 (16) Å	T = 150 K
c = 30.696 (10) Å	0.32 × 0.18 × 0.10 mm

Data collection top

Enraf-Nonius FAST system diffractometer	1724 reflections with I > 2σ(I)
11775 measured reflections	R_int = 0.073
2861 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.058	H-atom parameters constrained
S = 0.72	Δρ_max = 0.14 e Å⁻³
2861 reflections	Δρ_min = −0.15 e Å⁻³
409 parameters

Special details top

Experimental. Cell measurement and data collection using a FAST area detector system, details in Darr, Drake,Hursthouse and Malik, Inorg. Chem. 1993, 32, 5704. The data were collected by the EPSRC National X-Ray Crystallography Service(Professor M. Hursthouse) on their, now defunct, Nonius FAST diffractometer, while they were at Cardiff. They had set the instrument to theta = 25 °, setting error reduced this to 24.97 °.

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
C1A	0.0398 (4)	0.5407 (3)	0.20823 (13)	0.0341 (11)
H1A	−0.0566	0.5257	0.2022	0.044*
O1A	0.1111 (3)	0.4259 (2)	0.20226 (8)	0.0364 (7)
C2A	0.0583 (4)	0.5759 (3)	0.25646 (12)	0.0270 (10)
H2A	0.0034	0.6535	0.2621	0.035*
C3A	0.2012 (4)	0.6119 (3)	0.26443 (12)	0.0238 (10)
H3A	0.2590	0.5360	0.2591	0.031*
O3A	0.2157 (2)	0.6518 (2)	0.30893 (8)	0.0268 (6)
C4A	0.2411 (4)	0.7167 (3)	0.23397 (13)	0.0240 (10)
H4A	0.1843	0.7931	0.2395	0.031*
O4A	0.3774 (3)	0.7486 (2)	0.24179 (8)	0.0289 (7)
C5A	0.2245 (4)	0.6745 (3)	0.18700 (13)	0.0296 (10)
H5A	0.2835	0.5999	0.1811	0.039*
O5A	0.0876 (3)	0.6385 (2)	0.18049 (8)	0.0338 (7)
C6A	0.2530 (4)	0.7788 (3)	0.15447 (13)	0.0430 (12)
H6A1	0.2340	0.7479	0.1250	0.056*
H6A2	0.3467	0.8034	0.1565	0.056*
H6A3	0.1968	0.8526	0.1608	0.056*
C7A	0.0778 (5)	0.3650 (4)	0.16192 (14)	0.0624 (15)
H7A1	−0.0187	0.3546	0.1600	0.081*
H7A2	0.1206	0.2814	0.1606	0.081*
H7A3	0.1089	0.4175	0.1376	0.081*
N11A	0.0057 (4)	0.4734 (3)	0.28472 (11)	0.0383 (9)
N12A	0.0863 (4)	0.3844 (4)	0.29113 (12)	0.0427 (10)
N13A	0.1521 (4)	0.2985 (3)	0.30025 (15)	0.0665 (14)
C14A	0.3525 (4)	0.6849 (3)	0.31841 (13)	0.0306 (11)
O14A	0.4356 (3)	0.5802 (2)	0.31104 (9)	0.0355 (7)
C15A	0.4140 (4)	0.4712 (3)	0.33933 (14)	0.0507 (13)
H15A	0.4595	0.4850	0.3672	0.066*
H15B	0.4494	0.3945	0.3254	0.066*
H15C	0.3186	0.4605	0.3445	0.066*
C16A	0.3507 (4)	0.7283 (3)	0.36519 (11)	0.0351 (11)
H16A	0.3087	0.6629	0.3833	0.046*
H16B	0.3003	0.8077	0.3675	0.046*
H16C	0.4420	0.7424	0.3752	0.046*
C17A	0.4024 (4)	0.7873 (3)	0.28585 (12)	0.0286 (10)
O17A	0.3261 (2)	0.8975 (2)	0.29593 (9)	0.0343 (7)
C18A	0.3519 (5)	1.0064 (3)	0.26991 (14)	0.0487 (13)
H18A	0.4422	1.0370	0.2757	0.063*
H18B	0.2879	1.0734	0.2771	0.063*
H18C	0.3435	0.9839	0.2391	0.063*
C19A	0.5502 (4)	0.8097 (3)	0.28831 (13)	0.0361 (11)
H19A	0.5770	0.8683	0.2651	0.047*
H19B	0.5971	0.7287	0.2848	0.047*
H19C	0.5726	0.8468	0.3167	0.047*
C1B	0.2397 (5)	0.7960 (4)	−0.04450 (13)	0.0357 (11)
H1B	0.2619	0.7050	−0.0506	0.046*
O1B	0.3564 (3)	0.8691 (2)	−0.04779 (9)	0.0416 (8)
C2B	0.1932 (4)	0.8076 (3)	0.00278 (12)	0.0263 (10)
H2B	0.1130	0.7522	0.0059	0.034*
C3B	0.1481 (4)	0.9436 (3)	0.01098 (12)	0.0267 (10)
H3B	0.2251	1.0029	0.0076	0.035*
O3B	0.0965 (2)	0.9526 (2)	0.05450 (8)	0.0277 (7)
C4B	0.0421 (4)	0.9775 (3)	−0.02095 (13)	0.0290 (11)
H4B	−0.0364	0.9206	−0.0165	0.038*
O4B	0.0033 (3)	1.1076 (2)	−0.01350 (9)	0.0327 (7)
C5B	0.0916 (4)	0.9638 (3)	−0.06753 (12)	0.0343 (11)
H5B	0.1653	1.0257	−0.0730	0.045*
O5B	0.1400 (3)	0.8349 (2)	−0.07305 (8)	0.0405 (8)
C6B	−0.0179 (5)	0.9828 (4)	−0.10106 (13)	0.0480 (13)
H6B1	0.0185	0.9705	−0.1304	0.062*
H6B2	−0.0537	1.0692	−0.0985	0.062*
H6B3	−0.0890	0.9209	−0.0959	0.062*
C7B	0.4261 (5)	0.8501 (4)	−0.08829 (13)	0.0587 (14)
H7B1	0.4457	0.7594	−0.0920	0.076*
H7B2	0.5093	0.8985	−0.0879	0.076*
H7B3	0.3705	0.8794	−0.1125	0.076*
N11B	0.2933 (4)	0.7597 (3)	0.03366 (11)	0.0348 (10)
N12B	0.3825 (4)	0.8366 (3)	0.04247 (11)	0.0372 (10)
N13B	0.4718 (4)	0.8972 (3)	0.05397 (13)	0.0518 (11)
C14B	0.0498 (4)	1.0773 (3)	0.06461 (13)	0.0303 (11)
O14B	0.1544 (3)	1.1658 (2)	0.06267 (9)	0.0384 (8)
C15B	0.2679 (4)	1.1405 (4)	0.09004 (14)	0.0477 (13)
H15D	0.2492	1.1693	0.1198	0.062*
H15E	0.3455	1.1861	0.0787	0.062*
H15F	0.2862	1.0489	0.0902	0.062*
C16B	−0.0121 (4)	1.0656 (3)	0.10942 (12)	0.0390 (12)
H16D	0.0548	1.0351	0.1301	0.051*
H16E	−0.0862	1.0052	0.1083	0.051*
H16F	−0.0449	1.1490	0.1188	0.051*
C17B	−0.0511 (4)	1.1240 (3)	0.02886 (14)	0.0338 (11)
O17B	−0.1647 (3)	1.0467 (2)	0.03528 (9)	0.0385 (8)
C18B	−0.2718 (4)	1.0732 (4)	0.00631 (15)	0.0577 (15)
H18D	−0.3093	1.1569	0.0131	0.075*
H18E	−0.3406	1.0080	0.0096	0.075*
H18F	−0.2391	1.0730	−0.0238	0.075*
C19B	−0.0830 (4)	1.2656 (3)	0.03333 (14)	0.0431 (13)
H19D	−0.1355	1.2935	0.0082	0.056*
H19E	0.0000	1.3143	0.0345	0.056*
H19F	−0.1337	1.2799	0.0601	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.031 (3)	0.038 (3)	0.033 (3)	−0.005 (2)	0.002 (2)	−0.005 (2)
O1A	0.047 (2)	0.0307 (16)	0.0311 (18)	0.0026 (13)	−0.0013 (16)	−0.0123 (13)
C2A	0.031 (3)	0.030 (2)	0.020 (2)	−0.0025 (19)	0.002 (2)	−0.0035 (18)
C3A	0.026 (3)	0.026 (2)	0.019 (2)	0.0006 (18)	−0.001 (2)	−0.0068 (18)
O3A	0.0250 (18)	0.0323 (14)	0.0232 (17)	−0.0047 (12)	−0.0028 (14)	−0.0020 (12)
C4A	0.021 (3)	0.028 (2)	0.023 (2)	0.0004 (18)	0.000 (2)	0.0013 (19)
O4A	0.0255 (18)	0.0384 (15)	0.0228 (17)	−0.0025 (13)	−0.0001 (14)	−0.0065 (13)
C5A	0.026 (3)	0.030 (2)	0.033 (3)	0.001 (2)	−0.003 (2)	0.000 (2)
O5A	0.0293 (19)	0.0425 (17)	0.0296 (18)	0.0021 (14)	−0.0044 (15)	−0.0004 (13)
C6A	0.043 (3)	0.059 (3)	0.027 (3)	0.002 (2)	0.002 (2)	0.004 (2)
C7A	0.076 (4)	0.058 (3)	0.053 (4)	−0.002 (3)	−0.005 (3)	−0.034 (3)
N11A	0.036 (2)	0.039 (2)	0.040 (3)	−0.0089 (19)	−0.002 (2)	−0.0003 (18)
N12A	0.040 (3)	0.045 (3)	0.043 (3)	−0.018 (2)	0.003 (2)	0.003 (2)
N13A	0.063 (3)	0.045 (2)	0.092 (4)	−0.009 (2)	−0.006 (3)	0.022 (2)
C14A	0.024 (3)	0.034 (2)	0.034 (3)	0.002 (2)	−0.003 (2)	−0.004 (2)
O14A	0.0307 (19)	0.0412 (17)	0.0345 (19)	0.0038 (13)	−0.0030 (15)	0.0004 (14)
C15A	0.054 (3)	0.048 (3)	0.050 (3)	0.003 (2)	−0.008 (3)	0.013 (2)
C16A	0.040 (3)	0.045 (2)	0.020 (3)	−0.012 (2)	−0.005 (2)	0.000 (2)
C17A	0.027 (3)	0.036 (2)	0.022 (3)	−0.003 (2)	0.003 (2)	−0.0033 (19)
O17A	0.0399 (19)	0.0265 (15)	0.0366 (19)	−0.0002 (13)	0.0112 (16)	−0.0024 (14)
C18A	0.067 (4)	0.027 (2)	0.052 (3)	−0.009 (2)	0.012 (3)	−0.002 (2)
C19A	0.029 (3)	0.046 (2)	0.033 (3)	−0.006 (2)	0.007 (2)	−0.007 (2)
C1B	0.048 (3)	0.032 (2)	0.027 (3)	0.004 (2)	0.003 (3)	0.001 (2)
O1B	0.049 (2)	0.0420 (17)	0.0336 (19)	−0.0019 (16)	0.0181 (17)	−0.0024 (14)
C2B	0.029 (3)	0.024 (2)	0.026 (3)	−0.0001 (18)	0.002 (2)	−0.0015 (18)
C3B	0.036 (3)	0.023 (2)	0.021 (3)	−0.0029 (19)	0.001 (2)	0.0046 (18)
O3B	0.0357 (18)	0.0260 (15)	0.0214 (16)	0.0057 (12)	0.0031 (15)	−0.0010 (12)
C4B	0.035 (3)	0.021 (2)	0.031 (3)	−0.0023 (19)	−0.003 (2)	0.0021 (18)
O4B	0.0394 (19)	0.0280 (15)	0.0309 (19)	0.0026 (13)	0.0007 (15)	0.0066 (12)
C5B	0.045 (3)	0.031 (2)	0.028 (3)	−0.004 (2)	−0.001 (2)	0.0061 (19)
O5B	0.066 (2)	0.0344 (17)	0.0212 (18)	−0.0049 (16)	−0.0056 (17)	−0.0014 (13)
C6B	0.066 (4)	0.046 (3)	0.032 (3)	−0.015 (2)	−0.014 (3)	0.008 (2)
C7B	0.075 (4)	0.065 (3)	0.036 (3)	0.005 (3)	0.024 (3)	0.003 (2)
N11B	0.040 (3)	0.030 (2)	0.034 (2)	0.0043 (18)	0.005 (2)	−0.0008 (17)
N12B	0.040 (3)	0.043 (2)	0.029 (2)	0.017 (2)	0.001 (2)	−0.0016 (19)
N13B	0.043 (3)	0.060 (3)	0.052 (3)	0.007 (2)	−0.012 (2)	−0.002 (2)
C14B	0.028 (3)	0.025 (2)	0.038 (3)	0.002 (2)	0.002 (2)	−0.002 (2)
O14B	0.0315 (19)	0.0291 (16)	0.055 (2)	−0.0027 (14)	−0.0022 (17)	−0.0022 (14)
C15B	0.040 (3)	0.055 (3)	0.048 (3)	0.006 (2)	−0.011 (3)	−0.015 (2)
C16B	0.045 (3)	0.042 (3)	0.031 (3)	0.011 (2)	0.006 (2)	−0.005 (2)
C17B	0.035 (3)	0.031 (2)	0.036 (3)	0.002 (2)	0.009 (2)	0.007 (2)
O17B	0.0254 (19)	0.0363 (16)	0.054 (2)	−0.0024 (14)	−0.0008 (16)	0.0140 (15)
C18B	0.029 (3)	0.063 (3)	0.082 (4)	−0.003 (2)	−0.016 (3)	0.019 (3)
C19B	0.045 (3)	0.030 (2)	0.054 (3)	0.009 (2)	0.007 (3)	0.005 (2)

Geometric parameters (Å, º) top

C1A—O1A	1.416 (4)	C1B—O5B	1.394 (5)
C1A—O5A	1.419 (4)	C1B—O1B	1.407 (5)
C1A—C2A	1.537 (5)	C1B—C2B	1.530 (5)
O1A—C7A	1.434 (4)	O1B—C7B	1.441 (4)
C2A—N11A	1.481 (5)	C2B—N11B	1.472 (5)
C2A—C3A	1.507 (5)	C2B—C3B	1.521 (5)
C3A—O3A	1.436 (4)	C3B—O3B	1.436 (4)
C3A—C4A	1.500 (5)	C3B—C4B	1.492 (5)
O3A—C14A	1.449 (4)	O3B—C14B	1.426 (4)
C4A—O4A	1.432 (4)	C4B—O4B	1.441 (4)
C4A—C5A	1.518 (5)	C4B—C5B	1.521 (5)
O4A—C17A	1.435 (4)	O4B—C17B	1.421 (4)
C5A—O5A	1.443 (4)	C5B—O5B	1.450 (4)
C5A—C6A	1.510 (5)	C5B—C6B	1.521 (5)
N11A—N12A	1.254 (5)	N11B—N12B	1.238 (4)
N12A—N13A	1.154 (4)	N12B—N13B	1.157 (5)
C14A—O14A	1.400 (4)	C14B—O14B	1.406 (4)
C14A—C16A	1.507 (5)	C14B—C16B	1.515 (5)
C14A—C17A	1.553 (5)	C14B—C17B	1.574 (5)
O14A—C15A	1.454 (4)	O14B—C15B	1.443 (4)
C17A—O17A	1.423 (4)	C17B—O17B	1.416 (4)
C17A—C19A	1.509 (5)	C17B—C19B	1.530 (5)
O17A—C18A	1.420 (4)	O17B—C18B	1.425 (4)

O1A—C1A—O5A	111.6 (3)	O5B—C1B—O1B	113.3 (3)
O1A—C1A—C2A	105.5 (3)	O5B—C1B—C2B	110.7 (3)
O5A—C1A—C2A	111.3 (3)	O1B—C1B—C2B	106.3 (3)
C1A—O1A—C7A	111.9 (3)	C1B—O1B—C7B	113.1 (3)
N11A—C2A—C3A	115.4 (3)	N11B—C2B—C3B	114.8 (3)
N11A—C2A—C1A	110.2 (3)	N11B—C2B—C1B	112.0 (3)
C3A—C2A—C1A	109.4 (3)	C3B—C2B—C1B	108.9 (3)
O3A—C3A—C4A	110.5 (3)	O3B—C3B—C4B	109.7 (3)
O3A—C3A—C2A	109.0 (3)	O3B—C3B—C2B	108.9 (3)
C4A—C3A—C2A	109.8 (3)	C4B—C3B—C2B	109.2 (3)
C3A—O3A—C14A	111.0 (3)	C14B—O3B—C3B	112.5 (3)
O4A—C4A—C3A	108.9 (3)	O4B—C4B—C3B	108.4 (3)
O4A—C4A—C5A	109.4 (3)	O4B—C4B—C5B	109.1 (3)
C3A—C4A—C5A	110.4 (3)	C3B—C4B—C5B	111.1 (3)
C4A—O4A—C17A	113.1 (3)	C17B—O4B—C4B	111.3 (3)
O5A—C5A—C6A	106.3 (3)	O5B—C5B—C4B	107.9 (3)
O5A—C5A—C4A	108.3 (3)	O5B—C5B—C6B	106.7 (3)
C6A—C5A—C4A	113.3 (3)	C4B—C5B—C6B	112.7 (4)
C1A—O5A—C5A	115.5 (3)	C1B—O5B—C5B	116.2 (3)
N12A—N11A—C2A	113.8 (3)	N12B—N11B—C2B	114.4 (3)
N13A—N12A—N11A	173.2 (5)	N13B—N12B—N11B	171.7 (4)
O14A—C14A—O3A	110.3 (3)	O14B—C14B—O3B	110.6 (3)
O14A—C14A—C16A	113.5 (3)	O14B—C14B—C16B	113.6 (3)
O3A—C14A—C16A	104.7 (3)	O3B—C14B—C16B	105.0 (3)
O14A—C14A—C17A	104.3 (3)	O14B—C14B—C17B	104.3 (3)
O3A—C14A—C17A	110.1 (3)	O3B—C14B—C17B	110.3 (3)
C16A—C14A—C17A	114.0 (3)	C16B—C14B—C17B	113.1 (3)
C14A—O14A—C15A	115.7 (3)	C14B—O14B—C15B	116.5 (3)
O17A—C17A—O4A	110.0 (3)	O17B—C17B—O4B	111.7 (3)
O17A—C17A—C19A	113.2 (3)	O17B—C17B—C19B	112.1 (3)
O4A—C17A—C19A	105.3 (3)	O4B—C17B—C19B	106.3 (3)
O17A—C17A—C14A	104.5 (3)	O17B—C17B—C14B	104.2 (3)
O4A—C17A—C14A	110.7 (3)	O4B—C17B—C14B	110.6 (3)
C19A—C17A—C14A	113.3 (3)	C19B—C17B—C14B	112.1 (3)
C18A—O17A—C17A	115.8 (3)	C17B—O17B—C18B	114.3 (3)

Experimental details

Crystal data
Chemical formula	C₁₃H₂₃N₃O₆
M_r	317.34
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	150
a, b, c (Å)	10.065 (4), 10.512 (16), 30.696 (10)
V (Å³)	3248 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.32 × 0.18 × 0.10

Data collection
Diffractometer	Enraf-Nonius FAST system diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11775, 2861, 1724
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.058, 0.72
No. of reflections	2861
No. of parameters	409
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.15

Computer programs: MADNES (Pflugrath & Messerschmidt, 1990), MADNES, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLUTON92 (Spek, 1992) and PLATON92 (Spek, 1992), SHELXL97.

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Methyl (2′R,3′R)-2-azido-2,6-di­deoxy-3,4-O-(2′,3′-di­methoxy­butane-2′,3′-diyl)-α-L-gluco­pyran­oside

Supporting information

Key indicators

checkCIF results

Methyl (2′R,3′R)-2-azido-2,6-dideoxy-3,4-O-(2′,3′-dimethoxybutane-2′,3′-diyl)-α-L-glucopyranoside