Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title mol­ecule, C8H11NO4, the pyran­oside ring adopts a flattened E5 conformation in which five of the six ring atoms are coplanar, and the sixth atom is displaced from this plane. The structure of this mol­ecule differs little from that of the diastereomer in which the stereochemistry at the anomeric centre is inverted.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019507/lh2087sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019507/lh2087IIsup2.hkl
Contains datablock II

CCDC reference: 613767

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.090
  • Data-to-parameter ratio = 8.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.61 mm
Alert level G REFLT03_ALERT_4_G 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. From the CIF: _diffrn_reflns_theta_max 26.39 From the CIF: _reflns_number_total 1042 Count of symmetry unique reflns 1042 Completeness (_total/calc) 100.00% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: SHELXTL (Sheldrick, 1997a); software used to prepare material for publication: SHELXTL.

Methyl 2,3-amino-3-N,4-O-carbonyl-2,3-N-cyclo-2,3,6-trideoxy-α-L– allopyranoside top
Crystal data top
C8H11NO4Dx = 1.430 Mg m3
Mr = 185.18Melting point: 366 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5664 reflections
a = 6.3749 (5) Åθ = 2.5–26.4°
b = 9.9173 (7) ŵ = 0.12 mm1
c = 13.601 (1) ÅT = 193 K
V = 859.88 (11) Å3Block, colourless
Z = 40.61 × 0.25 × 0.14 mm
F(000) = 392
Data collection top
Bruker PLATFORM
diffractometer/SMART 1000 CCD area-detector
1042 independent reflections
Radiation source: fine-focus sealed tube1000 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 8.192 pixels mm-1θmax = 26.4°, θmin = 2.5°
ω scansh = 77
Absorption correction: integration
(SHELXTL; Sheldrick, 1997a)
k = 1212
Tmin = 0.947, Tmax = 0.984l = 1617
6587 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0636P)2 + 0.1002P]
where P = (Fo2 + 2Fc2)/3
1042 reflections(Δ/σ)max = 0.001
118 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.15 e Å3
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*/Ueq
O10.2936 (2)0.47470 (12)0.13798 (9)0.0307 (3)
O20.4789 (2)0.66962 (13)0.13951 (9)0.0304 (3)
O30.3174 (2)0.36792 (12)0.04477 (10)0.0320 (3)
O40.6241 (2)0.47021 (17)0.07456 (12)0.0424 (4)
N0.3163 (3)0.59623 (15)0.07052 (11)0.0277 (3)
C10.2811 (3)0.61622 (16)0.12249 (13)0.0258 (4)
H10.17960.65600.17040.031*
C20.2160 (3)0.65385 (16)0.01991 (12)0.0265 (4)
H20.16880.74950.01270.032*
C30.1005 (3)0.55735 (17)0.04217 (13)0.0252 (4)
H30.02170.58860.08230.030*
C40.1134 (3)0.41101 (17)0.00863 (14)0.0263 (4)
H40.00200.35580.03790.032*
C50.1161 (3)0.39881 (19)0.10258 (14)0.0303 (4)
H50.14080.30190.11910.036*
C60.0912 (3)0.4400 (2)0.14845 (16)0.0408 (5)
H6A0.08230.43090.22010.049*
H6B0.20330.38160.12350.049*
H6C0.12210.53390.13140.049*
C70.5366 (4)0.6733 (2)0.24080 (14)0.0435 (5)
H7A0.67680.71280.24740.052*
H7B0.53750.58140.26730.052*
H7C0.43520.72810.27730.052*
C80.4386 (3)0.47754 (19)0.06076 (13)0.0295 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0339 (7)0.0208 (6)0.0376 (7)0.0042 (5)0.0088 (6)0.0059 (5)
O20.0332 (7)0.0298 (6)0.0281 (6)0.0087 (6)0.0048 (5)0.0003 (5)
O30.0268 (6)0.0239 (6)0.0453 (7)0.0040 (5)0.0017 (6)0.0037 (5)
O40.0240 (7)0.0520 (9)0.0511 (9)0.0022 (6)0.0042 (6)0.0043 (7)
N0.0260 (7)0.0278 (7)0.0295 (7)0.0021 (6)0.0013 (6)0.0026 (6)
C10.0266 (8)0.0204 (7)0.0305 (8)0.0014 (7)0.0005 (7)0.0001 (6)
C20.0264 (8)0.0193 (7)0.0338 (8)0.0005 (7)0.0015 (7)0.0016 (6)
C30.0223 (8)0.0233 (8)0.0301 (8)0.0006 (7)0.0035 (6)0.0023 (6)
C40.0211 (8)0.0221 (8)0.0357 (9)0.0008 (7)0.0005 (7)0.0025 (7)
C50.0316 (9)0.0205 (7)0.0388 (9)0.0056 (7)0.0030 (8)0.0047 (7)
C60.0379 (11)0.0430 (11)0.0414 (10)0.0120 (10)0.0099 (9)0.0016 (8)
C70.0493 (13)0.0491 (12)0.0320 (9)0.0007 (11)0.0101 (10)0.0094 (8)
C80.0260 (9)0.0325 (9)0.0300 (8)0.0004 (7)0.0007 (7)0.0020 (7)
Geometric parameters (Å, º) top
O1—C11.4214 (19)C2—H21.0000
O1—C51.442 (2)C3—C41.524 (2)
O2—C11.387 (2)C3—H31.0000
O2—C71.426 (2)C4—C51.517 (3)
O3—C81.352 (2)C4—H41.0000
O3—C41.454 (2)C5—C61.518 (3)
O4—C81.199 (2)C5—H51.0000
N—C81.418 (2)C6—H6A0.9800
N—C31.480 (2)C6—H6B0.9800
N—C21.499 (2)C6—H6C0.9800
C1—C21.503 (2)C7—H7A0.9800
C1—H11.0000C7—H7B0.9800
C2—C31.474 (2)C7—H7C0.9800
C1—O1—C5114.95 (14)C5—C4—C3112.03 (15)
C1—O2—C7113.91 (15)O3—C4—H4111.2
C8—O3—C4109.23 (13)C5—C4—H4111.2
C8—N—C3105.71 (13)C3—C4—H4111.2
C8—N—C2118.29 (14)O1—C5—C4107.47 (15)
C3—N—C259.29 (11)O1—C5—C6113.95 (15)
O2—C1—O1107.53 (15)C4—C5—C6112.24 (17)
O2—C1—C2108.13 (14)O1—C5—H5107.6
O1—C1—C2113.48 (14)C4—C5—H5107.6
O2—C1—H1109.2C6—C5—H5107.6
O1—C1—H1109.2C5—C6—H6A109.5
C2—C1—H1109.2C5—C6—H6B109.5
C3—C2—N59.70 (11)H6A—C6—H6B109.5
C3—C2—C1120.58 (15)C5—C6—H6C109.5
N—C2—C1123.32 (15)H6A—C6—H6C109.5
C3—C2—H2114.2H6B—C6—H6C109.5
N—C2—H2114.2O2—C7—H7A109.5
C1—C2—H2114.2O2—C7—H7B109.5
C2—C3—N61.01 (11)H7A—C7—H7B109.5
C2—C3—C4114.83 (14)O2—C7—H7C109.5
N—C3—C4106.01 (14)H7A—C7—H7C109.5
C2—C3—H3120.1H7B—C7—H7C109.5
N—C3—H3120.1O4—C8—O3122.70 (19)
C4—C3—H3120.1O4—C8—N125.31 (19)
O3—C4—C5107.66 (15)O3—C8—N111.59 (15)
O3—C4—C3103.13 (14)
C7—O2—C1—O173.01 (18)C8—O3—C4—C321.04 (17)
C7—O2—C1—C2164.10 (16)C2—C3—C4—O379.71 (17)
C5—O1—C1—O2166.72 (14)N—C3—C4—O314.72 (17)
C5—O1—C1—C247.2 (2)C2—C3—C4—C535.8 (2)
C8—N—C2—C392.17 (16)N—C3—C4—C5100.77 (18)
C8—N—C2—C116.6 (2)C1—O1—C5—C465.86 (19)
C3—N—C2—C1108.72 (18)C1—O1—C5—C659.2 (2)
O2—C1—C2—C3141.44 (16)O3—C4—C5—O154.60 (18)
O1—C1—C2—C322.2 (2)C3—C4—C5—O158.1 (2)
O2—C1—C2—N69.67 (19)O3—C4—C5—C6179.35 (14)
O1—C1—C2—N49.5 (2)C3—C4—C5—C667.9 (2)
C1—C2—C3—N113.19 (18)C4—O3—C8—O4166.99 (19)
N—C2—C3—C495.22 (16)C4—O3—C8—N19.96 (19)
C1—C2—C3—C418.0 (2)C3—N—C8—O4177.66 (19)
C8—N—C3—C2113.93 (15)C2—N—C8—O4114.5 (2)
C8—N—C3—C44.02 (17)C3—N—C8—O39.50 (18)
C2—N—C3—C4109.91 (15)C2—N—C8—O372.7 (2)
C8—O3—C4—C597.54 (17)
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds