The structure of the title compound, C8H13NO4, shows the oxazolidone ring to be essentially planar, which forces the pyranoside ring into a 2SO skew-boat conformation. The CH3 and OCH3 groups both adopt pseudo-equatorial orientations.
Supporting information
CCDC reference: 610830
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (C-C) = 0.003 Å
- R factor = 0.035
- wR factor = 0.079
- Data-to-parameter ratio = 9.4
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.739 0.989
Tmin(prime) and Tmax expected: 0.937 0.989
RR(prime) = 0.789
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.79
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
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 26.40
From the CIF: _reflns_number_total 1114
Count of symmetry unique reflns 1112
Completeness (_total/calc) 100.18%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2
Fraction of Friedel pairs measured 0.002
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 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
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.
methyl
3-amino-3-
N,4-
O-carbonyl-2,3,6-trideoxy-
α-
L-
lyxo-hexopyranoside
top
Crystal data top
C8H13NO4 | Dx = 1.375 Mg m−3 |
Mr = 187.19 | Melting point: 390 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1719 reflections |
a = 5.2411 (8) Å | θ = 2.3–23.7° |
b = 10.2928 (16) Å | µ = 0.11 mm−1 |
c = 16.760 (3) Å | T = 193 K |
V = 904.1 (2) Å3 | Rod, colourless |
Z = 4 | 0.59 × 0.12 × 0.10 mm |
F(000) = 400 | |
Data collection top
Bruker SMART 1000 CCD area detector/PLATFORM diffractometer | 1114 independent reflections |
Radiation source: fine-focus sealed tube | 940 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
Detector resolution: 8.192 pixels mm-1 | θmax = 26.4°, θmin = 2.3° |
ω scans | h = −6→6 |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | k = −12→12 |
Tmin = 0.739, Tmax = 0.989 | l = −18→20 |
6168 measured reflections | |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0377P)2 + 0.1378P] where P = (Fo2 + 2Fc2)/3 |
1114 reflections | (Δ/σ)max < 0.001 |
118 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
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 | Uiso*/Ueq | |
O1 | 0.3424 (3) | 0.43448 (14) | 0.39952 (9) | 0.0281 (4) | |
O2 | 0.1518 (3) | 0.25412 (13) | 0.33959 (9) | 0.0283 (4) | |
O3 | 0.2438 (3) | 0.70392 (14) | 0.43647 (9) | 0.0319 (4) | |
O4 | 0.3947 (4) | 0.83464 (15) | 0.33993 (10) | 0.0396 (4) | |
N | 0.0851 (4) | 0.68113 (17) | 0.31545 (12) | 0.0319 (5) | |
H1N | 0.0704 | 0.6910 | 0.2635 | 0.038* | |
C1 | 0.1977 (4) | 0.3902 (2) | 0.33401 (14) | 0.0257 (5) | |
H1 | 0.2935 | 0.4085 | 0.2837 | 0.031* | |
C2 | −0.0644 (5) | 0.4523 (2) | 0.32874 (14) | 0.0296 (5) | |
H2A | −0.1876 | 0.3987 | 0.3591 | 0.036* | |
H2B | −0.1199 | 0.4533 | 0.2723 | 0.036* | |
C3 | −0.0697 (5) | 0.5905 (2) | 0.36109 (13) | 0.0287 (5) | |
H3 | −0.2497 | 0.6224 | 0.3641 | 0.034* | |
C4 | 0.0582 (5) | 0.6006 (2) | 0.44389 (13) | 0.0281 (5) | |
H4 | −0.0716 | 0.6235 | 0.4853 | 0.034* | |
C5 | 0.1930 (5) | 0.4765 (2) | 0.46646 (14) | 0.0280 (5) | |
H5 | 0.0623 | 0.4085 | 0.4786 | 0.034* | |
C6 | 0.3684 (5) | 0.4903 (2) | 0.53725 (16) | 0.0396 (6) | |
H6A | 0.4486 | 0.4064 | 0.5488 | 0.047* | |
H6B | 0.2699 | 0.5189 | 0.5838 | 0.047* | |
H6C | 0.5006 | 0.5547 | 0.5252 | 0.047* | |
C7 | 0.3807 (5) | 0.1794 (2) | 0.33806 (15) | 0.0370 (6) | |
H7A | 0.3388 | 0.0870 | 0.3430 | 0.044* | |
H7B | 0.4906 | 0.2055 | 0.3826 | 0.044* | |
H7C | 0.4702 | 0.1945 | 0.2876 | 0.044* | |
C8 | 0.2515 (5) | 0.7480 (2) | 0.35963 (14) | 0.0292 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0238 (8) | 0.0279 (8) | 0.0324 (9) | −0.0005 (7) | −0.0019 (8) | −0.0050 (7) |
O2 | 0.0306 (8) | 0.0206 (7) | 0.0338 (9) | −0.0003 (7) | −0.0005 (8) | −0.0021 (7) |
O3 | 0.0425 (10) | 0.0250 (8) | 0.0282 (9) | −0.0064 (8) | −0.0017 (8) | −0.0025 (7) |
O4 | 0.0466 (10) | 0.0279 (9) | 0.0443 (10) | −0.0103 (8) | −0.0052 (10) | 0.0056 (8) |
N | 0.0395 (11) | 0.0269 (10) | 0.0292 (10) | −0.0024 (10) | −0.0070 (10) | 0.0010 (8) |
C1 | 0.0296 (12) | 0.0212 (10) | 0.0263 (12) | −0.0026 (9) | −0.0011 (10) | −0.0008 (10) |
C2 | 0.0281 (12) | 0.0265 (12) | 0.0342 (14) | −0.0016 (10) | −0.0044 (11) | −0.0022 (10) |
C3 | 0.0230 (11) | 0.0254 (12) | 0.0379 (14) | 0.0041 (10) | −0.0026 (11) | −0.0027 (10) |
C4 | 0.0279 (12) | 0.0252 (12) | 0.0311 (13) | −0.0012 (10) | 0.0049 (11) | −0.0054 (10) |
C5 | 0.0295 (13) | 0.0283 (12) | 0.0262 (12) | −0.0049 (10) | 0.0024 (11) | −0.0001 (9) |
C6 | 0.0475 (15) | 0.0390 (14) | 0.0321 (13) | −0.0075 (14) | −0.0072 (14) | 0.0039 (11) |
C7 | 0.0397 (15) | 0.0267 (12) | 0.0445 (15) | 0.0056 (11) | 0.0004 (14) | −0.0002 (11) |
C8 | 0.0313 (12) | 0.0230 (11) | 0.0333 (13) | 0.0036 (11) | −0.0027 (11) | −0.0018 (10) |
Geometric parameters (Å, º) top
O1—C1 | 1.410 (3) | C2—H2B | 0.9900 |
O1—C5 | 1.435 (3) | C3—C4 | 1.545 (3) |
O2—C1 | 1.424 (2) | C3—H3 | 1.0000 |
O2—C7 | 1.425 (3) | C4—C5 | 1.508 (3) |
O3—C4 | 1.447 (3) | C4—H4 | 1.0000 |
O3—C8 | 1.366 (3) | C5—C6 | 1.508 (3) |
O4—C8 | 1.212 (3) | C5—H5 | 1.0000 |
N—C3 | 1.454 (3) | C6—H6A | 0.9800 |
N—C8 | 1.335 (3) | C6—H6B | 0.9800 |
N—H1N | 0.8800 | C6—H6C | 0.9800 |
C1—C2 | 1.518 (3) | C7—H7A | 0.9800 |
C1—H1 | 1.0000 | C7—H7B | 0.9800 |
C2—C3 | 1.522 (3) | C7—H7C | 0.9800 |
C2—H2A | 0.9900 | | |
| | | |
C1—O1—C5 | 114.36 (16) | O3—C4—H4 | 110.1 |
C1—O2—C7 | 112.79 (17) | C3—C4—C5 | 111.81 (18) |
C4—O3—C8 | 110.17 (17) | C3—C4—H4 | 110.1 |
C3—N—C8 | 113.8 (2) | C5—C4—H4 | 110.1 |
C3—N—H1N | 123.1 | O1—C5—C4 | 108.35 (18) |
C8—N—H1N | 123.1 | O1—C5—C6 | 108.11 (19) |
O1—C1—O2 | 110.95 (18) | O1—C5—H5 | 108.8 |
O1—C1—C2 | 113.31 (18) | C4—C5—C6 | 113.75 (19) |
O2—C1—C2 | 105.41 (17) | C4—C5—H5 | 108.8 |
O1—C1—H1 | 109.0 | C6—C5—H5 | 108.8 |
O2—C1—H1 | 109.0 | C5—C6—H6A | 109.5 |
C2—C1—H1 | 109.0 | C5—C6—H6B | 109.5 |
C1—C2—C3 | 112.93 (19) | C5—C6—H6C | 109.5 |
C1—C2—H2A | 109.0 | H6A—C6—H6B | 109.5 |
C1—C2—H2B | 109.0 | H6A—C6—H6C | 109.5 |
C3—C2—H2A | 109.0 | H6B—C6—H6C | 109.5 |
C3—C2—H2B | 109.0 | O2—C7—H7A | 109.5 |
H2A—C2—H2B | 107.8 | O2—C7—H7B | 109.5 |
N—C3—C2 | 113.69 (19) | O2—C7—H7C | 109.5 |
N—C3—C4 | 100.78 (18) | H7A—C7—H7B | 109.5 |
N—C3—H3 | 110.0 | H7A—C7—H7C | 109.5 |
C2—C3—C4 | 112.03 (19) | H7B—C7—H7C | 109.5 |
C2—C3—H3 | 110.0 | O3—C8—N | 109.4 (2) |
C4—C3—H3 | 110.0 | O4—C8—N | 129.3 (2) |
O3—C4—C3 | 105.32 (17) | O3—C8—O4 | 121.3 (2) |
O3—C4—C5 | 109.24 (18) | | |
| | | |
C5—O1—C1—O2 | −90.4 (2) | C3—N—C8—O4 | −175.4 (2) |
C5—O1—C1—C2 | 28.0 (3) | O1—C1—C2—C3 | 31.2 (3) |
C1—O1—C5—C4 | −69.5 (2) | O2—C1—C2—C3 | 152.66 (18) |
C1—O1—C5—C6 | 166.80 (17) | C1—C2—C3—N | 64.7 (3) |
C7—O2—C1—O1 | −62.1 (2) | C1—C2—C3—C4 | −48.8 (3) |
C7—O2—C1—C2 | 174.87 (18) | N—C3—C4—O3 | 6.3 (2) |
C8—O3—C4—C3 | −4.1 (2) | N—C3—C4—C5 | −112.2 (2) |
C8—O3—C4—C5 | 116.1 (2) | C2—C3—C4—O3 | 127.5 (2) |
C4—O3—C8—O4 | −179.9 (2) | C2—C3—C4—C5 | 9.0 (3) |
C4—O3—C8—N | −0.2 (3) | O3—C4—C5—O1 | −69.3 (2) |
C8—N—C3—C2 | −127.1 (2) | O3—C4—C5—C6 | 50.9 (3) |
C8—N—C3—C4 | −7.0 (3) | C3—C4—C5—O1 | 46.9 (2) |
C3—N—C8—O3 | 4.9 (3) | C3—C4—C5—C6 | 167.1 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N—H1N···O2i | 0.88 | 2.18 | 2.976 (3) | 150 |
Symmetry code: (i) −x, y+1/2, −z+1/2. |