Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049252/ng2332sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049252/ng2332Isup2.hkl |
CCDC reference: 667344
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.038
- wR factor = 0.100
- Data-to-parameter ratio = 9.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT301_ALERT_3_C Main Residue Disorder ......................... 21.00 Perc. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C1 - C2 ... 1.33 Ang.
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 26.50 From the CIF: _reflns_number_total 1369 Count of symmetry unique reflns 1380 Completeness (_total/calc) 99.20% 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 2 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 1 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 0 ALERT type 5 Informative message, check
For the synthesis of the t-butyl 2-formylallylcarbamate reactant, see Erkkila & Pihko (2006). For the conversion of 1,2-dioxines to carbohydrates, see Robinson et al. (2006) and Pedersen & Rosenbohm (2001) for some experimental techiques. For calculations on ring puckering, see Cremer & Pople (1975).
Diphenylmethylphosphonium iodide (41.8 g, 103 mmol) was suspended in anhydrous THF (350 ml) and cooled to 0 °C. Potassium tert-butoxide (11.56 g, 103 mmol) was added in one portion to give a yellow slurry that was allowed to warm to room temperature. tert-butyl 2-formylallylcarbamate (Erkkila & Pihko, 2006) (17.4 g, 94 mmol) was dissolved in anhydrous THF (150 ml) and added to the above suspension by cannula. The resulting mixture was stirred vigorusly overnight under an atmosphere of nitrogen. Half saturated aqueous ammonium chloride (50 ml) was added and the THF removed in vacuo. The aqueous phase was transferred to a separatory funnel with water (200 ml) and extracted with 20% ethyl acetate in hexanes, v/v (200 ml + 3 x 100 ml). The combined organic phases were dried (Na2SO4), filtered and concentrated in vacuo to give a yellow gum. Purification by Dry Column Vacuum Chromatography (Pedersen & Rosenbohm, 2001) (id 6 cm; 20 ml fractions; 10 x hexanes; 2–20% EtOAc in hexanes, v/v - 2% increments; 10 x 20% EtOAc in hexanes, v/v) gave tert-butyl 2-methylenebut-3-enylcarbamate (3.0 g, 17%) as a tan liquid. This diene (3.0 g, 16.4 mmol) was dissolved in dichloromethane (90 ml), Rose Bengal bis-triethylammonium salt (100 mg) was added and the solution photolysed for 24 h whilst a stream of oxygen was bubbled through the solution. The solvent was removed in vacuo to give a pink gum that was purified by Dry Column Vacuum Chromatography (id 4 cm; 20 ml fractions; 8 x hexanes; 5 - 60% EtOAc in hexanes, v/v - 5% increments) to give dioxine (I) (0.90 g, 26%) as needles.
All H atoms were included in the riding-model approximation, with C—H = 0.95 to 0.99 Å and N—H = 0.88 Å, and with Uiso(H) = 1.2Ueq(C, N) and Uiso(H) = 1.5Ueq(methyl-C). Disorder was noted in the C4—O1—O2—C4 residue of the six-membered ring and two positions were discerned for the O atoms. The major component (anisotropic) had a site occupancy factor = 0.706 (5). The absolute structure could not be determined with confidence so the Friedel pairs were averaged.
Recently, we reported that 1,2-dioxines can be converted to a wide variety of carbohydrates by dihydroxylation of the olefin, followed by cleavage of the peroxide bond (Robinson et al., 2006). To extend this methodology further, a number of amino dioxines were synthesized, such as the title compound, C10H17NO4 (I), that could potentially be converted to amino sugars by the same method.
The molecular structure of (I), Fig. 1, features a six-membered ring with a half-chair conformation so that the O atoms lie on either side of the plane defined by the four C atoms. The ring is characterized by a puckering amplitude = 0.618 (2) Å, and values of θ = 52.10 (19)° and φ = 28.0 (3)° (Cremer & Pople, 1975). The overall conformation of the molecule is such that the ring lies to one side of the central chromophore. Molecules are connected into a supramolecular chain aligned along the b axis by N—H···O hydrogen bonding interactions (Fig. 2 & Table 1). Chains are consolidated into a 3-D structure via C—H···O interactions (Fig. 3).
For the synthesis of the t-butyl 2-formylallylcarbamate reactant, see Erkkila & Pihko (2006). For the conversion of 1,2-dioxines to carbohydrates, see Robinson et al. (2006) and Pedersen & Rosenbohm (2001) for some experimental techiques. For calculations on ring puckering, see Cremer & Pople (1975).
Data collection: CrystalClear (Rigaku Americas Corporation, 2005); cell refinement: CrystalClear (Rigaku Americas Corporation, 2005); data reduction: CrystalClear (Rigaku Americas Corporation, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C10H17NO4 | F(000) = 464 |
Mr = 215.25 | Dx = 1.239 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4236 reflections |
a = 9.435 (4) Å | θ = 2.2–30.4° |
b = 9.628 (4) Å | µ = 0.10 mm−1 |
c = 12.698 (6) Å | T = 120 K |
V = 1153.6 (9) Å3 | Prism, colorless |
Z = 4 | 0.40 × 0.40 × 0.10 mm |
Rigaku AFC12κ/SATURN724 diffractometer | 1347 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 26.5°, θmin = 2.7° |
ω scans | h = −10→11 |
11678 measured reflections | k = −10→12 |
1369 independent reflections | l = −15→15 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0581P)2 + 0.2125P] where P = (Fo2 + 2Fc2)/3 |
1369 reflections | (Δ/σ)max < 0.001 |
145 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C10H17NO4 | V = 1153.6 (9) Å3 |
Mr = 215.25 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 9.435 (4) Å | µ = 0.10 mm−1 |
b = 9.628 (4) Å | T = 120 K |
c = 12.698 (6) Å | 0.40 × 0.40 × 0.10 mm |
Rigaku AFC12κ/SATURN724 diffractometer | 1347 reflections with I > 2σ(I) |
11678 measured reflections | Rint = 0.027 |
1369 independent reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.14 e Å−3 |
1369 reflections | Δρmin = −0.16 e Å−3 |
145 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O3 | 0.45338 (14) | 0.52172 (13) | 0.69574 (12) | 0.0403 (3) | |
O4 | 0.33495 (14) | 0.72768 (13) | 0.68622 (11) | 0.0370 (3) | |
C3 | 0.8147 (3) | 0.6760 (3) | 1.05230 (18) | 0.0568 (6) | 0.706 (5) |
H3A | 0.8892 | 0.6070 | 1.0690 | 0.068* | 0.706 (5) |
H3B | 0.8385 | 0.7636 | 1.0891 | 0.068* | 0.706 (5) |
C4 | 0.6062 (2) | 0.5477 (2) | 0.92708 (15) | 0.0393 (4) | 0.706 (5) |
H4A | 0.5147 | 0.5971 | 0.9347 | 0.047* | 0.706 (5) |
H4B | 0.5905 | 0.4671 | 0.8801 | 0.047* | 0.706 (5) |
O1 | 0.6742 (3) | 0.6237 (2) | 1.09082 (16) | 0.0500 (8) | 0.706 (5) |
O2 | 0.6513 (2) | 0.4980 (2) | 1.02975 (15) | 0.0429 (7) | 0.706 (5) |
C3A | 0.8147 (3) | 0.6760 (3) | 1.05230 (18) | 0.0568 (6) | 0.294 (5) |
H3C | 0.9137 | 0.6753 | 1.0782 | 0.068* | 0.294 (5) |
H3D | 0.7621 | 0.7501 | 1.0896 | 0.068* | 0.294 (5) |
C4A | 0.6062 (2) | 0.5477 (2) | 0.92708 (15) | 0.0393 (4) | 0.294 (5) |
H4C | 0.5113 | 0.5591 | 0.8949 | 0.047* | 0.294 (5) |
H4D | 0.6361 | 0.4497 | 0.9199 | 0.047* | 0.294 (5) |
O1A | 0.7525 (6) | 0.5504 (6) | 1.0696 (4) | 0.0480 (18)* | 0.294 (5) |
O2A | 0.6048 (6) | 0.5901 (6) | 1.0373 (4) | 0.0443 (16)* | 0.294 (5) |
N1 | 0.56110 (16) | 0.72726 (15) | 0.73168 (12) | 0.0330 (3) | |
H1 | 0.5514 | 0.8181 | 0.7329 | 0.040* | |
C1 | 0.71146 (19) | 0.64320 (18) | 0.87711 (14) | 0.0317 (4) | |
C2 | 0.8118 (2) | 0.7010 (2) | 0.93588 (16) | 0.0402 (5) | |
H2 | 0.8817 | 0.7582 | 0.9041 | 0.048* | |
C5 | 0.69754 (18) | 0.6658 (2) | 0.76017 (14) | 0.0336 (4) | |
H5A | 0.7748 | 0.7278 | 0.7360 | 0.040* | |
H5B | 0.7083 | 0.5757 | 0.7235 | 0.040* | |
C6 | 0.45012 (19) | 0.64797 (18) | 0.70358 (13) | 0.0314 (4) | |
C7 | 0.2026 (2) | 0.6673 (2) | 0.64337 (17) | 0.0412 (5) | |
C8 | 0.1393 (2) | 0.5642 (2) | 0.7209 (2) | 0.0512 (6) | |
H8A | 0.2016 | 0.4832 | 0.7268 | 0.077* | |
H8B | 0.0458 | 0.5347 | 0.6960 | 0.077* | |
H8C | 0.1298 | 0.6084 | 0.7901 | 0.077* | |
C9 | 0.1067 (2) | 0.7929 (3) | 0.6341 (3) | 0.0623 (7) | |
H9A | 0.0893 | 0.8317 | 0.7042 | 0.093* | |
H9B | 0.0164 | 0.7651 | 0.6022 | 0.093* | |
H9C | 0.1523 | 0.8632 | 0.5897 | 0.093* | |
C10 | 0.2326 (3) | 0.6033 (3) | 0.53635 (19) | 0.0593 (7) | |
H10A | 0.2947 | 0.5225 | 0.5450 | 0.089* | |
H10B | 0.2792 | 0.6721 | 0.4912 | 0.089* | |
H10C | 0.1433 | 0.5740 | 0.5038 | 0.089* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O3 | 0.0397 (7) | 0.0282 (7) | 0.0530 (8) | −0.0002 (5) | −0.0028 (6) | −0.0033 (6) |
O4 | 0.0308 (6) | 0.0281 (6) | 0.0521 (7) | −0.0014 (5) | −0.0070 (6) | −0.0002 (6) |
C3 | 0.0668 (15) | 0.0525 (13) | 0.0513 (12) | −0.0174 (13) | −0.0236 (12) | 0.0077 (10) |
C4 | 0.0340 (9) | 0.0463 (11) | 0.0376 (9) | −0.0043 (8) | −0.0034 (8) | 0.0026 (8) |
O1 | 0.0606 (15) | 0.0528 (14) | 0.0366 (10) | −0.0119 (12) | 0.0015 (11) | −0.0054 (9) |
O2 | 0.0519 (12) | 0.0383 (12) | 0.0384 (10) | −0.0098 (10) | −0.0043 (9) | 0.0065 (8) |
C3A | 0.0668 (15) | 0.0525 (13) | 0.0513 (12) | −0.0174 (13) | −0.0236 (12) | 0.0077 (10) |
C4A | 0.0340 (9) | 0.0463 (11) | 0.0376 (9) | −0.0043 (8) | −0.0034 (8) | 0.0026 (8) |
N1 | 0.0326 (8) | 0.0274 (7) | 0.0390 (8) | −0.0008 (6) | −0.0047 (6) | 0.0008 (6) |
C1 | 0.0297 (8) | 0.0268 (8) | 0.0386 (9) | 0.0035 (7) | −0.0015 (7) | −0.0013 (7) |
C2 | 0.0384 (10) | 0.0337 (9) | 0.0484 (10) | −0.0047 (9) | −0.0084 (9) | 0.0022 (8) |
C5 | 0.0274 (8) | 0.0344 (9) | 0.0391 (9) | −0.0002 (7) | 0.0009 (7) | 0.0005 (7) |
C6 | 0.0330 (9) | 0.0282 (8) | 0.0329 (8) | −0.0008 (7) | −0.0008 (7) | 0.0002 (7) |
C7 | 0.0292 (9) | 0.0395 (10) | 0.0551 (11) | −0.0065 (8) | −0.0074 (9) | 0.0022 (9) |
C8 | 0.0383 (10) | 0.0475 (12) | 0.0677 (14) | −0.0083 (9) | 0.0038 (10) | 0.0065 (11) |
C9 | 0.0337 (10) | 0.0512 (13) | 0.102 (2) | −0.0017 (11) | −0.0148 (12) | 0.0145 (14) |
C10 | 0.0469 (12) | 0.0782 (18) | 0.0527 (12) | −0.0201 (13) | −0.0100 (10) | −0.0062 (12) |
O3—C6 | 1.220 (2) | N1—C6 | 1.344 (2) |
O4—C6 | 1.349 (2) | N1—C5 | 1.462 (2) |
O4—C7 | 1.481 (2) | N1—H1 | 0.8800 |
C3—O1 | 1.500 (4) | C1—C2 | 1.327 (3) |
C3—C2 | 1.498 (3) | C1—C5 | 1.507 (3) |
C3—H3A | 0.9900 | C2—H2 | 0.9500 |
C3—H3B | 0.9900 | C5—H5A | 0.9900 |
C4—O2 | 1.453 (3) | C5—H5B | 0.9900 |
C4—C1 | 1.495 (3) | C7—C9 | 1.515 (3) |
C4—H4A | 0.9900 | C7—C10 | 1.519 (3) |
C4—H4B | 0.9900 | C7—C8 | 1.520 (3) |
O1—O2 | 1.454 (3) | C8—H8A | 0.9800 |
C3A—O1A | 1.362 (6) | C8—H8B | 0.9800 |
C3A—C2 | 1.498 (3) | C8—H8C | 0.9800 |
C3A—H3C | 0.9900 | C9—H9A | 0.9800 |
C3A—H3D | 0.9900 | C9—H9B | 0.9800 |
C4A—O2A | 1.458 (6) | C9—H9C | 0.9800 |
C4A—C1 | 1.495 (3) | C10—H10A | 0.9800 |
C4A—H4C | 0.9900 | C10—H10B | 0.9800 |
C4A—H4D | 0.9900 | C10—H10C | 0.9800 |
O1A—O2A | 1.502 (8) | ||
C6—O4—C7 | 121.07 (14) | C1—C2—C3A | 120.0 (2) |
O1—C3—C2 | 111.0 (2) | C1—C2—H2 | 120.0 |
O1—C3—H3A | 109.4 | C3—C2—H2 | 120.0 |
C2—C3—H3A | 109.4 | C3A—C2—H2 | 120.0 |
O1—C3—H3B | 109.4 | N1—C5—C1 | 112.28 (15) |
C2—C3—H3B | 109.4 | N1—C5—H5A | 109.1 |
H3A—C3—H3B | 108.0 | C1—C5—H5A | 109.1 |
O2—C4—C1 | 112.89 (17) | N1—C5—H5B | 109.1 |
O2—C4—H4A | 109.0 | C1—C5—H5B | 109.1 |
C1—C4—H4A | 109.0 | H5A—C5—H5B | 107.9 |
O2—C4—H4B | 109.0 | O3—C6—N1 | 124.61 (17) |
C1—C4—H4B | 109.0 | O3—C6—O4 | 125.03 (17) |
H4A—C4—H4B | 107.8 | N1—C6—O4 | 110.36 (14) |
O2—O1—C3 | 103.7 (2) | O4—C7—C9 | 102.64 (17) |
C4—O2—O1 | 104.33 (18) | O4—C7—C10 | 109.30 (17) |
O1A—C3A—C2 | 107.1 (3) | C9—C7—C10 | 111.4 (2) |
O1A—C3A—H3C | 110.3 | O4—C7—C8 | 110.44 (17) |
C2—C3A—H3C | 110.3 | C9—C7—C8 | 109.71 (19) |
O1A—C3A—H3D | 110.3 | C10—C7—C8 | 112.8 (2) |
C2—C3A—H3D | 110.3 | C7—C8—H8A | 109.5 |
H3C—C3A—H3D | 108.6 | C7—C8—H8B | 109.5 |
O2A—C4A—C1 | 104.0 (3) | H8A—C8—H8B | 109.5 |
O2A—C4A—H4C | 111.0 | C7—C8—H8C | 109.5 |
C1—C4A—H4C | 111.0 | H8A—C8—H8C | 109.5 |
O2A—C4A—H4D | 111.0 | H8B—C8—H8C | 109.5 |
C1—C4A—H4D | 111.0 | C7—C9—H9A | 109.5 |
H4C—C4A—H4D | 109.0 | C7—C9—H9B | 109.5 |
C3A—O1A—O2A | 97.5 (4) | H9A—C9—H9B | 109.5 |
C4A—O2A—O1A | 100.5 (4) | C7—C9—H9C | 109.5 |
C6—N1—C5 | 121.46 (14) | H9A—C9—H9C | 109.5 |
C6—N1—H1 | 119.3 | H9B—C9—H9C | 109.5 |
C5—N1—H1 | 119.3 | C7—C10—H10A | 109.5 |
C2—C1—C4 | 119.53 (17) | C7—C10—H10B | 109.5 |
C2—C1—C4A | 119.53 (17) | H10A—C10—H10B | 109.5 |
C2—C1—C5 | 123.74 (18) | C7—C10—H10C | 109.5 |
C4—C1—C5 | 116.71 (16) | H10A—C10—H10C | 109.5 |
C4A—C1—C5 | 116.71 (16) | H10B—C10—H10C | 109.5 |
C1—C2—C3 | 120.0 (2) | ||
C2—C3—O1—O2 | 58.0 (2) | C5—C1—C2—C3A | 178.1 (2) |
C1—C4—O2—O1 | 57.4 (2) | O1—C3—C2—C1 | −18.2 (3) |
C3—O1—O2—C4 | −77.6 (2) | O1—C3—C2—C3A | 0 (100) |
C2—C3A—O1A—O2A | −67.3 (4) | O1A—C3A—C2—C1 | 27.2 (4) |
C1—C4A—O2A—O1A | −66.0 (4) | O1A—C3A—C2—C3 | 0 (100) |
C3A—O1A—O2A—C4A | 93.9 (4) | C6—N1—C5—C1 | −93.6 (2) |
O2—C4—C1—C2 | −16.9 (3) | C2—C1—C5—N1 | −120.2 (2) |
O2—C4—C1—C4A | 0 (11) | C4—C1—C5—N1 | 60.9 (2) |
O2—C4—C1—C5 | 162.06 (17) | C4A—C1—C5—N1 | 60.9 (2) |
O2A—C4A—C1—C2 | 24.3 (3) | C5—N1—C6—O3 | −2.6 (3) |
O2A—C4A—C1—C4 | 0 (38) | C5—N1—C6—O4 | 176.90 (14) |
O2A—C4A—C1—C5 | −156.7 (3) | C7—O4—C6—O3 | −7.0 (3) |
C4—C1—C2—C3 | −3.0 (3) | C7—O4—C6—N1 | 173.47 (15) |
C4A—C1—C2—C3 | −3.0 (3) | C6—O4—C7—C9 | −178.27 (18) |
C5—C1—C2—C3 | 178.1 (2) | C6—O4—C7—C10 | −59.9 (2) |
C4—C1—C2—C3A | −3.0 (3) | C6—O4—C7—C8 | 64.8 (2) |
C4A—C1—C2—C3A | −3.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.88 | 2.16 | 2.984 (2) | 156 |
C3—H3A···O3ii | 0.99 | 2.52 | 3.425 (3) | 152 |
C4—H4B···O4iii | 0.99 | 2.55 | 3.446 (3) | 150 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+3/2, −y+1, z+1/2; (iii) −x+1, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C10H17NO4 |
Mr | 215.25 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 120 |
a, b, c (Å) | 9.435 (4), 9.628 (4), 12.698 (6) |
V (Å3) | 1153.6 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.40 × 0.40 × 0.10 |
Data collection | |
Diffractometer | Rigaku AFC12κ/SATURN724 |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11678, 1369, 1347 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.100, 1.07 |
No. of reflections | 1369 |
No. of parameters | 145 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.16 |
Computer programs: CrystalClear (Rigaku Americas Corporation, 2005), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.88 | 2.16 | 2.984 (2) | 156 |
C3—H3A···O3ii | 0.99 | 2.52 | 3.425 (3) | 152 |
C4—H4B···O4iii | 0.99 | 2.55 | 3.446 (3) | 150 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+3/2, −y+1, z+1/2; (iii) −x+1, y−1/2, −z+3/2. |
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Recently, we reported that 1,2-dioxines can be converted to a wide variety of carbohydrates by dihydroxylation of the olefin, followed by cleavage of the peroxide bond (Robinson et al., 2006). To extend this methodology further, a number of amino dioxines were synthesized, such as the title compound, C10H17NO4 (I), that could potentially be converted to amino sugars by the same method.
The molecular structure of (I), Fig. 1, features a six-membered ring with a half-chair conformation so that the O atoms lie on either side of the plane defined by the four C atoms. The ring is characterized by a puckering amplitude = 0.618 (2) Å, and values of θ = 52.10 (19)° and φ = 28.0 (3)° (Cremer & Pople, 1975). The overall conformation of the molecule is such that the ring lies to one side of the central chromophore. Molecules are connected into a supramolecular chain aligned along the b axis by N—H···O hydrogen bonding interactions (Fig. 2 & Table 1). Chains are consolidated into a 3-D structure via C—H···O interactions (Fig. 3).