Methyl 2,3-amino-3-N,4-O-carbonyl-2,3-N-cyclo-2,3,6-tride­oxy-β-L-allopyran­oside

In the structure of the title compound, C₈H₁₁NO₄, the aziridine and oxazolidinone rings induce flattening of the pyran­oside ring, resulting in five of the six pyran­oside ring atoms being nearly coplanar. The pyran­oside ring thus adopts an E₅ conformation, the methyl and meth­oxy substituents both being pseudo-axially disposed.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.029
• wR factor = 0.082
• Data-to-parameter ratio = 9.1

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:      0.746     0.972
            Tmin(prime) and Tmax expected:      0.931     0.972
            RR(prime) =      0.801
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.80
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.62 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           26.38
           From the CIF: _reflns_number_total               1076
           Count of symmetry unique reflns         1076
           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
   3 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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 2,3-amino-3-N,4-O-carbonyl-2,3-N-cyclo-2,3,6-trideoxy-α-L-allopyranoside

Crystal data

C8H11NO4	Dx = 1.405 Mg m^−3
Mr = 185.18	Melting point: 416 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6292 reflections
a = 5.7376 (6) Å	θ = 2.2–26.3°
b = 9.3890 (9) Å	µ = 0.11 mm^−1
c = 16.2562 (16) Å	T = 193 K
V = 875.73 (15) Å^3	Prism, colorless
Z = 4	0.62 × 0.30 × 0.25 mm
F(000) = 392

Data collection

Bruker SMART 1000 CCD area detector/PLATFORM diffractometer	1076 independent reflections
Radiation source: fine-focus sealed tube	1014 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 8.192 pixels mm^-1	θmax = 26.4°, θmin = 2.5°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2003)	k = −11→11
Tmin = 0.746, Tmax = 0.972	l = −20→20
6970 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0517P)^2 + 0.1153P] where P = (Fo^2 + 2Fc^2)/3
1076 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.14 e Å^−3

Special details

Experimental. IR 1787, 1136, 1110, 1077 cm^-1.

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.4202 (2)	0.08677 (12)	0.37044 (7)	0.0345 (3)
O2	0.3579 (3)	−0.10326 (15)	0.27907 (8)	0.0459 (4)
O3	0.2786 (2)	0.11112 (12)	0.52861 (7)	0.0380 (3)
O4	0.5914 (3)	−0.01120 (15)	0.57114 (9)	0.0486 (4)
N	0.2850 (3)	−0.12917 (14)	0.50668 (9)	0.0376 (4)
C1	0.4269 (3)	−0.06206 (19)	0.35832 (10)	0.0354 (4)
H1	0.5905	−0.0952	0.3673	0.042*
C2	0.2702 (3)	−0.14453 (18)	0.41484 (11)	0.0376 (4)
H2	0.2305	−0.2426	0.3953	0.045*
C3	0.0829 (3)	−0.07273 (18)	0.46091 (11)	0.0389 (4)
H3	−0.0731	−0.1192	0.4666	0.047*
C4	0.1032 (3)	0.08819 (18)	0.46511 (11)	0.0369 (4)
H4	−0.0488	0.1328	0.4807	0.044*
C5	0.1963 (3)	0.15052 (17)	0.38601 (10)	0.0370 (4)
H5	0.2235	0.2543	0.3960	0.044*
C6	0.0244 (4)	0.1390 (2)	0.31579 (13)	0.0516 (5)
H6A	0.0913	0.1825	0.2664	0.062*
H6B	−0.1200	0.1886	0.3305	0.062*
H6C	−0.0096	0.0384	0.3050	0.062*
C7	0.5067 (5)	−0.0484 (3)	0.21614 (12)	0.0619 (6)
H7A	0.4505	−0.0802	0.1623	0.074*
H7B	0.6658	−0.0831	0.2248	0.074*
H7C	0.5057	0.0560	0.2182	0.074*
C8	0.4068 (3)	−0.00846 (17)	0.53677 (10)	0.0350 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0334 (6)	0.0337 (6)	0.0364 (6)	−0.0084 (5)	0.0051 (5)	−0.0046 (5)
O2	0.0461 (8)	0.0517 (7)	0.0401 (6)	0.0014 (7)	−0.0059 (6)	−0.0165 (6)
O3	0.0529 (8)	0.0250 (5)	0.0361 (5)	0.0038 (6)	0.0093 (6)	−0.0017 (4)
O4	0.0505 (8)	0.0463 (7)	0.0491 (7)	0.0012 (7)	−0.0089 (7)	−0.0052 (6)
N	0.0429 (8)	0.0247 (6)	0.0453 (7)	−0.0006 (7)	−0.0011 (7)	0.0038 (6)
C1	0.0323 (9)	0.0359 (8)	0.0379 (8)	0.0041 (7)	−0.0028 (8)	−0.0117 (7)
C2	0.0438 (10)	0.0228 (7)	0.0462 (9)	−0.0010 (7)	−0.0095 (8)	−0.0029 (6)
C3	0.0308 (8)	0.0331 (8)	0.0528 (9)	−0.0046 (8)	0.0017 (8)	0.0099 (8)
C4	0.0347 (9)	0.0296 (8)	0.0465 (9)	0.0078 (8)	0.0095 (8)	0.0052 (7)
C5	0.0453 (9)	0.0238 (7)	0.0419 (9)	0.0020 (8)	0.0048 (8)	0.0047 (7)
C6	0.0509 (11)	0.0482 (10)	0.0557 (11)	0.0113 (10)	−0.0085 (10)	0.0063 (10)
C7	0.0628 (14)	0.0868 (16)	0.0362 (9)	0.0043 (13)	0.0027 (9)	−0.0182 (11)
C8	0.0425 (9)	0.0283 (8)	0.0340 (7)	0.0009 (8)	0.0054 (8)	−0.0003 (6)

Geometric parameters (Å, º)

O1—C1	1.412 (2)	C2—H2	1.0000
O1—C5	1.440 (2)	C3—C4	1.517 (2)
O2—C1	1.4020 (19)	C3—H3	1.0000
O2—C7	1.429 (3)	C4—C5	1.510 (2)
O3—C4	1.458 (2)	C4—H4	1.0000
O3—C8	1.349 (2)	C5—C6	1.513 (3)
O4—C8	1.198 (3)	C5—H5	1.0000
N—C2	1.502 (2)	C6—H6A	0.9800
N—C3	1.476 (2)	C6—H6B	0.9800
N—C8	1.419 (2)	C6—H6C	0.9800
C1—C2	1.501 (3)	C7—H7A	0.9800
C1—H1	1.0000	C7—H7B	0.9800
C2—C3	1.473 (3)	C7—H7C	0.9800
C1—O1—C5	117.39 (14)	O3—C4—H4	111.2
C1—O2—C7	112.94 (16)	C3—C4—C5	112.02 (15)
C4—O3—C8	108.86 (12)	C3—C4—H4	111.2
C2—N—C3	59.27 (12)	C5—C4—H4	111.2
C2—N—C8	116.57 (14)	O1—C5—C4	107.71 (13)
C3—N—C8	105.90 (13)	O1—C5—C6	114.80 (14)
O1—C1—O2	113.19 (15)	O1—C5—H5	107.1
O1—C1—C2	114.15 (14)	C4—C5—C6	112.59 (16)
O1—C1—H1	108.2	C4—C5—H5	107.1
O2—C1—C2	104.54 (14)	C6—C5—H5	107.1
O2—C1—H1	108.2	C5—C6—H6A	109.5
C2—C1—H1	108.2	C5—C6—H6B	109.5
N—C2—C1	121.67 (15)	C5—C6—H6C	109.5
N—C2—C3	59.47 (11)	H6A—C6—H6B	109.5
N—C2—H2	114.6	H6A—C6—H6C	109.5
C1—C2—C3	120.81 (15)	H6B—C6—H6C	109.5
C1—C2—H2	114.6	O2—C7—H7A	109.5
C3—C2—H2	114.6	O2—C7—H7B	109.5
N—C3—C2	61.25 (12)	O2—C7—H7C	109.5
N—C3—C4	105.93 (15)	H7A—C7—H7B	109.5
N—C3—H3	120.0	H7A—C7—H7C	109.5
C2—C3—C4	115.00 (15)	H7B—C7—H7C	109.5
C2—C3—H3	120.0	O3—C8—O4	123.09 (16)
C4—C3—H3	120.0	O3—C8—N	111.25 (15)
O3—C4—C3	103.42 (14)	O4—C8—N	125.41 (16)
O3—C4—C5	107.56 (15)
C5—O1—C1—O2	78.93 (18)	C3—N—C8—O3	12.18 (18)
C5—O1—C1—C2	−40.5 (2)	C3—N—C8—O4	−173.41 (16)
C1—O1—C5—C4	62.15 (17)	O1—C1—C2—N	−54.9 (2)
C1—O1—C5—C6	−64.13 (19)	O1—C1—C2—C3	16.1 (2)
C7—O2—C1—O1	62.2 (2)	O2—C1—C2—N	−179.07 (15)
C7—O2—C1—C2	−172.97 (17)	O2—C1—C2—C3	−108.15 (17)
C8—O3—C4—C3	21.27 (17)	N—C2—C3—C4	95.15 (17)
C8—O3—C4—C5	−97.39 (15)	C1—C2—C3—N	−110.98 (17)
C4—O3—C8—O4	163.76 (16)	C1—C2—C3—C4	−15.8 (2)
C4—O3—C8—N	−21.69 (18)	N—C3—C4—O3	−13.38 (18)
C3—N—C2—C1	109.56 (19)	N—C3—C4—C5	102.15 (17)
C8—N—C2—C1	16.2 (2)	C2—C3—C4—O3	−78.62 (17)
C8—N—C2—C3	−93.39 (16)	C2—C3—C4—C5	36.9 (2)
C2—N—C3—C4	−110.16 (16)	O3—C4—C5—O1	54.93 (16)
C8—N—C3—C2	111.82 (15)	O3—C4—C5—C6	−177.49 (13)
C8—N—C3—C4	1.66 (18)	C3—C4—C5—O1	−58.0 (2)
C2—N—C8—O3	75.34 (19)	C3—C4—C5—C6	69.5 (2)
C2—N—C8—O4	−110.3 (2)