Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031546/lh2449sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031546/lh2449Isup2.hkl |
CCDC reference: 657675
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.031
- wR factor = 0.074
- Data-to-parameter ratio = 10.8
checkCIF/PLATON results
No syntax errors found
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 27.45 From the CIF: _reflns_number_total 1370 Count of symmetry unique reflns 1398 Completeness (_total/calc) 98.00% 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 PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 4 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 0 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 related literature see: Curran et al. (2007); Jones et al. (2007); Hotchkiss et al. (2006).
Treatment of 1-deoxy-3-C-methyl-D-psicose 2 (Jones et al. in preparation) derived from 2-C-methyl-D-ribono-1,4-lactone 1 (Hotchkiss et al., 2006), with sodium cyanide, gave a mixture of 2,6-anhydro derivative 3 and lactone 4 (Curran et al. 2007) (Fig. 3). X-ray analysis firmly established the structure of the title compound as the 2,6-anhydro furanose 3. m.p. 321–326 K; [α]D22 -47.0 (c, 1.0 in acetone).
In the absence of significant anomalous scattering, Friedel pairs were merged and the absolute configuration was assigned from the starting material.
The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.93–0.98, O—H = 0.82 Å) and Uiso(H) (in the range 1.2–1.5 times Ueq of the parent atom), after which the positions were refined with riding constraints.
For background information see the previous paper (Curran et al., 2007). The crystal structure of the title compound (Fig. 1) exists as alternating layers of molecules running parallel to the ab-face (Fig.2). There is no hydrogen bonding.
For related literature see: Curran et al. (2007); Jones et al. (2007); Hotchkiss et al. (2006).
Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.
C10H16O4 | F(000) = 432 |
Mr = 200.23 | Dx = 1.277 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1321 reflections |
a = 6.6307 (2) Å | θ = 5–27° |
b = 11.1029 (4) Å | µ = 0.10 mm−1 |
c = 14.1409 (5) Å | T = 150 K |
V = 1041.05 (6) Å3 | Plate, colourless |
Z = 4 | 0.60 × 0.50 × 0.10 mm |
Nonius KappaCCD diffractometer | 1160 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
ω scans | θmax = 27.5°, θmin = 5.3° |
Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997) | h = −8→8 |
Tmin = 0.95, Tmax = 1.00 | k = −14→14 |
6557 measured reflections | l = −18→18 |
1370 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.074 | w = 1/[σ2(F2) + (0.03P)2 + 0.18P], where P = [max(Fo2,0) + 2Fc2]/3 |
S = 0.93 | (Δ/σ)max = 0.000171 |
1370 reflections | Δρmax = 0.24 e Å−3 |
127 parameters | Δρmin = −0.19 e Å−3 |
0 restraints |
C10H16O4 | V = 1041.05 (6) Å3 |
Mr = 200.23 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.6307 (2) Å | µ = 0.10 mm−1 |
b = 11.1029 (4) Å | T = 150 K |
c = 14.1409 (5) Å | 0.60 × 0.50 × 0.10 mm |
Nonius KappaCCD diffractometer | 1370 independent reflections |
Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997) | 1160 reflections with I > 2σ(I) |
Tmin = 0.95, Tmax = 1.00 | Rint = 0.045 |
6557 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.074 | H-atom parameters constrained |
S = 0.93 | Δρmax = 0.24 e Å−3 |
1370 reflections | Δρmin = −0.19 e Å−3 |
127 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3568 (2) | 0.21011 (14) | 0.20100 (10) | 0.0212 | |
C2 | 0.4422 (2) | 0.31928 (14) | 0.14619 (10) | 0.0217 | |
O3 | 0.56240 (17) | 0.37828 (10) | 0.21534 (8) | 0.0263 | |
C4 | 0.6883 (2) | 0.27622 (15) | 0.23612 (11) | 0.0272 | |
C5 | 0.5351 (2) | 0.18346 (15) | 0.26887 (10) | 0.0245 | |
O6 | 0.46475 (18) | 0.21350 (13) | 0.36068 (7) | 0.0352 | |
C7 | 0.2509 (3) | 0.22921 (16) | 0.35888 (11) | 0.0270 | |
O8 | 0.19903 (16) | 0.25108 (11) | 0.26189 (7) | 0.0283 | |
C9 | 0.1985 (3) | 0.34073 (17) | 0.41531 (13) | 0.0403 | |
C10 | 0.1483 (3) | 0.11679 (18) | 0.39421 (13) | 0.0396 | |
C11 | 0.7600 (3) | 0.24199 (19) | 0.13709 (12) | 0.0353 | |
O12 | 0.58629 (17) | 0.27261 (11) | 0.07985 (8) | 0.0317 | |
C13 | 0.2974 (3) | 0.40276 (16) | 0.09881 (12) | 0.0305 | |
C14 | 0.2857 (3) | 0.10662 (15) | 0.13904 (12) | 0.0308 | |
H41 | 0.8009 | 0.2937 | 0.2816 | 0.0355* | |
H51 | 0.5810 | 0.0978 | 0.2636 | 0.0310* | |
H91 | 0.0522 | 0.3542 | 0.4084 | 0.0621* | |
H92 | 0.2310 | 0.3255 | 0.4825 | 0.0614* | |
H93 | 0.2804 | 0.4099 | 0.3910 | 0.0617* | |
H101 | 0.0017 | 0.1299 | 0.3883 | 0.0594* | |
H102 | 0.1804 | 0.1039 | 0.4613 | 0.0595* | |
H103 | 0.1903 | 0.0467 | 0.3550 | 0.0594* | |
H111 | 0.7881 | 0.1541 | 0.1327 | 0.0480* | |
H112 | 0.8841 | 0.2875 | 0.1191 | 0.0473* | |
H131 | 0.3743 | 0.4706 | 0.0698 | 0.0479* | |
H132 | 0.1972 | 0.4328 | 0.1459 | 0.0487* | |
H133 | 0.2281 | 0.3599 | 0.0465 | 0.0489* | |
H141 | 0.2242 | 0.0438 | 0.1796 | 0.0485* | |
H142 | 0.4037 | 0.0743 | 0.1055 | 0.0487* | |
H143 | 0.1825 | 0.1383 | 0.0923 | 0.0481* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0180 (7) | 0.0224 (8) | 0.0231 (7) | 0.0020 (7) | −0.0018 (6) | −0.0006 (7) |
C2 | 0.0217 (7) | 0.0228 (8) | 0.0207 (7) | 0.0003 (7) | −0.0004 (7) | −0.0020 (6) |
O3 | 0.0255 (6) | 0.0219 (5) | 0.0316 (6) | −0.0021 (5) | −0.0053 (5) | −0.0018 (5) |
C4 | 0.0185 (7) | 0.0304 (9) | 0.0326 (8) | 0.0012 (8) | −0.0031 (7) | 0.0014 (8) |
C5 | 0.0219 (8) | 0.0267 (8) | 0.0248 (7) | 0.0014 (8) | −0.0033 (7) | 0.0028 (7) |
O6 | 0.0274 (6) | 0.0560 (8) | 0.0221 (5) | 0.0010 (7) | −0.0034 (5) | 0.0044 (6) |
C7 | 0.0257 (8) | 0.0348 (10) | 0.0204 (7) | −0.0004 (8) | −0.0008 (6) | 0.0021 (7) |
O8 | 0.0205 (5) | 0.0431 (7) | 0.0214 (5) | 0.0029 (6) | 0.0011 (5) | 0.0025 (5) |
C9 | 0.0467 (12) | 0.0394 (10) | 0.0347 (9) | 0.0016 (10) | −0.0041 (9) | −0.0070 (8) |
C10 | 0.0441 (11) | 0.0375 (10) | 0.0372 (9) | −0.0035 (10) | 0.0063 (9) | 0.0071 (9) |
C11 | 0.0221 (8) | 0.0443 (11) | 0.0394 (10) | 0.0043 (9) | 0.0037 (8) | 0.0026 (9) |
O12 | 0.0273 (6) | 0.0415 (7) | 0.0262 (5) | 0.0031 (6) | 0.0057 (5) | 0.0001 (6) |
C13 | 0.0350 (10) | 0.0261 (8) | 0.0304 (8) | 0.0022 (9) | −0.0060 (8) | 0.0045 (7) |
C14 | 0.0323 (9) | 0.0254 (8) | 0.0348 (9) | −0.0029 (8) | −0.0085 (8) | −0.0010 (8) |
C1—C2 | 1.546 (2) | C7—C10 | 1.507 (3) |
C1—C5 | 1.551 (2) | C9—H91 | 0.986 |
C1—O8 | 1.4293 (18) | C9—H92 | 0.988 |
C1—C14 | 1.520 (2) | C9—H93 | 1.001 |
C2—O3 | 1.4214 (18) | C10—H101 | 0.986 |
C2—O12 | 1.4357 (18) | C10—H102 | 0.983 |
C2—C13 | 1.493 (2) | C10—H103 | 0.995 |
O3—C4 | 1.438 (2) | C11—O12 | 1.448 (2) |
C4—C5 | 1.519 (2) | C11—H111 | 0.995 |
C4—C11 | 1.527 (2) | C11—H112 | 0.998 |
C4—H41 | 1.004 | C13—H131 | 0.998 |
C5—O6 | 1.4193 (19) | C13—H132 | 0.999 |
C5—H51 | 1.001 | C13—H133 | 0.993 |
O6—C7 | 1.429 (2) | C14—H141 | 0.991 |
C7—O8 | 1.4348 (18) | C14—H142 | 0.983 |
C7—C9 | 1.514 (2) | C14—H143 | 1.014 |
C2—C1—C5 | 100.40 (12) | C7—O8—C1 | 110.27 (12) |
C2—C1—O8 | 108.70 (12) | C7—C9—H91 | 107.3 |
C5—C1—O8 | 104.24 (11) | C7—C9—H92 | 108.4 |
C2—C1—C14 | 114.66 (13) | H91—C9—H92 | 109.6 |
C5—C1—C14 | 116.67 (13) | C7—C9—H93 | 108.8 |
O8—C1—C14 | 111.16 (13) | H91—C9—H93 | 112.5 |
C1—C2—O3 | 102.81 (11) | H92—C9—H93 | 110.0 |
C1—C2—O12 | 106.76 (12) | C7—C10—H101 | 107.1 |
O3—C2—O12 | 104.05 (12) | C7—C10—H102 | 110.0 |
C1—C2—C13 | 118.43 (14) | H101—C10—H102 | 108.4 |
O3—C2—C13 | 112.53 (13) | C7—C10—H103 | 109.6 |
O12—C2—C13 | 111.02 (13) | H101—C10—H103 | 110.2 |
C2—O3—C4 | 95.90 (11) | H102—C10—H103 | 111.4 |
O3—C4—C5 | 102.05 (13) | C4—C11—O12 | 101.92 (12) |
O3—C4—C11 | 100.93 (13) | C4—C11—H111 | 111.1 |
C5—C4—C11 | 108.61 (15) | O12—C11—H111 | 110.1 |
O3—C4—H41 | 114.2 | C4—C11—H112 | 111.4 |
C5—C4—H41 | 115.7 | O12—C11—H112 | 113.2 |
C11—C4—H41 | 113.8 | H111—C11—H112 | 109.0 |
C1—C5—C4 | 101.05 (12) | C11—O12—C2 | 104.40 (11) |
C1—C5—O6 | 105.70 (12) | C2—C13—H131 | 108.9 |
C4—C5—O6 | 109.83 (14) | C2—C13—H132 | 109.6 |
C1—C5—H51 | 111.5 | H131—C13—H132 | 111.3 |
C4—C5—H51 | 114.7 | C2—C13—H133 | 109.5 |
O6—C5—H51 | 113.0 | H131—C13—H133 | 107.0 |
C5—O6—C7 | 109.79 (12) | H132—C13—H133 | 110.5 |
O6—C7—O8 | 106.00 (12) | C1—C14—H141 | 109.1 |
O6—C7—C9 | 108.58 (16) | C1—C14—H142 | 107.9 |
O8—C7—C9 | 108.08 (14) | H141—C14—H142 | 110.5 |
O6—C7—C10 | 109.95 (16) | C1—C14—H143 | 108.8 |
O8—C7—C10 | 110.41 (14) | H141—C14—H143 | 110.0 |
C9—C7—C10 | 113.52 (15) | H142—C14—H143 | 110.5 |
Experimental details
Crystal data | |
Chemical formula | C10H16O4 |
Mr | 200.23 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 150 |
a, b, c (Å) | 6.6307 (2), 11.1029 (4), 14.1409 (5) |
V (Å3) | 1041.05 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.60 × 0.50 × 0.10 |
Data collection | |
Diffractometer | Nonius KappaCCD |
Absorption correction | Multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.95, 1.00 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6557, 1370, 1160 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.074, 0.93 |
No. of reflections | 1370 |
No. of parameters | 127 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.19 |
Computer programs: COLLECT (Nonius, 2001), DENZO/SCALEPACK (Otwinowski & Minor, 1997), DENZO/SCALEPACK, SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996), CRYSTALS.
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
For background information see the previous paper (Curran et al., 2007). The crystal structure of the title compound (Fig. 1) exists as alternating layers of molecules running parallel to the ab-face (Fig.2). There is no hydrogen bonding.