Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042292/bt2210sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042292/bt2210Isup2.hkl |
CCDC reference: 627362
Key indicators
- Single-crystal X-ray study
- T = 163 K
- Mean (C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.103
- Data-to-parameter ratio = 9.4
checkCIF/PLATON results
No syntax errors found
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.658 0.994 Tmin(prime) and Tmax expected: 0.922 0.995 RR(prime) = 0.715 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.71
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.96 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.63 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7
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 1701 Count of symmetry unique reflns 1718 Completeness (_total/calc) 99.01% 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 C2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S 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 2 ALERT level B = Potentially serious problem 4 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 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
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
C13H22O6 | F(000) = 592 |
Mr = 274.31 | Dx = 1.282 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5190 reflections |
a = 5.6670 (9) Å | θ = 2.2–13.3° |
b = 9.8516 (16) Å | µ = 0.10 mm−1 |
c = 25.447 (4) Å | T = 163 K |
V = 1420.7 (4) Å3 | Needle, colourless |
Z = 4 | 0.80 × 0.31 × 0.05 mm |
Bruker P4 CCD area-detector diffractometer | 1701 independent reflections |
Radiation source: fine-focus sealed tube | 1312 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
Detector resolution: 8.192 pixels mm-1 | θmax = 26.4°, θmin = 1.6° |
φ and ω scans | h = −7→3 |
Absorption correction: multi-scan (Blessing, 1995) | k = −12→12 |
Tmin = 0.658, Tmax = 0.994 | l = −31→31 |
18007 measured reflections |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0673P)2] where P = (Fo2 + 2Fc2)/3 |
1701 reflections | (Δ/σ)max < 0.001 |
180 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Experimental. Crystal decay was monitored by repeating the initial 10 frames at the end of the data collection and analyzing duplicate reflections. The standard 1.0 mm diameter collimator was used. |
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 | ||
O1 | 0.6325 (4) | 0.6862 (2) | 0.20001 (7) | 0.0455 (6) | |
O2 | 0.8544 (4) | 0.85974 (18) | 0.17091 (7) | 0.0375 (5) | |
O3 | 1.1899 (3) | 0.84150 (18) | 0.07463 (7) | 0.0293 (5) | |
O4 | 1.0525 (3) | 0.65201 (19) | 0.00322 (6) | 0.0296 (4) | |
H4O | 0.924 (5) | 0.665 (3) | −0.0144 (11) | 0.036* | |
O5 | 0.7754 (3) | 0.42109 (16) | 0.06337 (7) | 0.0286 (5) | |
O6 | 0.4813 (3) | 0.47161 (18) | 0.12194 (6) | 0.0329 (5) | |
C1 | 0.7705 (5) | 0.6306 (3) | 0.15807 (9) | 0.0283 (6) | |
H1 | 0.8562 | 0.5478 | 0.1704 | 0.034* | |
C2 | 0.9480 (5) | 0.7438 (3) | 0.14432 (9) | 0.0267 (6) | |
H2 | 1.1059 | 0.7207 | 0.1594 | 0.032* | |
C3 | 0.9738 (5) | 0.7728 (2) | 0.08578 (9) | 0.0235 (6) | |
H3 | 0.8372 | 0.8282 | 0.0732 | 0.028* | |
C4 | 0.9807 (5) | 0.6361 (2) | 0.05652 (9) | 0.0231 (6) | |
H4 | 1.1009 | 0.5779 | 0.0743 | 0.028* | |
C5 | 0.7436 (4) | 0.5654 (2) | 0.06161 (9) | 0.0221 (6) | |
H5 | 0.6424 | 0.5894 | 0.0308 | 0.027* | |
C6 | 0.6086 (5) | 0.5950 (2) | 0.11262 (10) | 0.0238 (6) | |
H6 | 0.4947 | 0.6709 | 0.1066 | 0.029* | |
C7 | 0.7363 (5) | 0.8113 (3) | 0.21655 (10) | 0.0360 (7) | |
C8 | 0.9062 (6) | 0.7851 (5) | 0.26123 (11) | 0.0655 (12) | |
H8A | 1.0321 | 0.7243 | 0.2492 | 0.098* | |
H8B | 0.8215 | 0.7427 | 0.2905 | 0.098* | |
H8C | 0.9751 | 0.8712 | 0.2729 | 0.098* | |
C9 | 0.5427 (7) | 0.9088 (4) | 0.23073 (14) | 0.0645 (11) | |
H9A | 0.6107 | 0.9982 | 0.2380 | 0.097* | |
H9B | 0.4597 | 0.8757 | 0.2620 | 0.097* | |
H9C | 0.4313 | 0.9159 | 0.2014 | 0.097* | |
C10 | 0.5686 (5) | 0.3663 (3) | 0.08720 (10) | 0.0276 (6) | |
C11 | 0.3800 (5) | 0.3340 (3) | 0.04687 (11) | 0.0337 (7) | |
H11A | 0.3472 | 0.4152 | 0.0258 | 0.051* | |
H11B | 0.2356 | 0.3052 | 0.0649 | 0.051* | |
H11C | 0.4353 | 0.2609 | 0.0238 | 0.051* | |
C12 | 0.6437 (6) | 0.2449 (3) | 0.11975 (12) | 0.0431 (8) | |
H12A | 0.7001 | 0.1726 | 0.0964 | 0.065* | |
H12B | 0.5089 | 0.2117 | 0.1402 | 0.065* | |
H12C | 0.7709 | 0.2717 | 0.1437 | 0.065* | |
C13 | 1.1855 (6) | 0.9836 (3) | 0.08597 (11) | 0.0448 (8) | |
H13A | 1.0540 | 1.0261 | 0.0672 | 0.067* | |
H13B | 1.3343 | 1.0250 | 0.0747 | 0.067* | |
H13C | 1.1653 | 0.9970 | 0.1239 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0562 (14) | 0.0468 (13) | 0.0336 (11) | −0.0225 (12) | 0.0148 (10) | −0.0138 (9) |
O2 | 0.0495 (13) | 0.0261 (10) | 0.0368 (10) | −0.0078 (10) | 0.0140 (10) | −0.0117 (8) |
O3 | 0.0282 (11) | 0.0196 (9) | 0.0401 (10) | −0.0054 (9) | 0.0042 (9) | −0.0027 (8) |
O4 | 0.0293 (11) | 0.0311 (10) | 0.0284 (10) | −0.0042 (9) | 0.0051 (8) | −0.0008 (8) |
O5 | 0.0262 (10) | 0.0184 (9) | 0.0413 (10) | −0.0008 (8) | 0.0053 (8) | −0.0050 (8) |
O6 | 0.0359 (11) | 0.0243 (10) | 0.0383 (10) | −0.0101 (9) | 0.0109 (9) | −0.0083 (8) |
C1 | 0.0363 (16) | 0.0231 (13) | 0.0254 (13) | −0.0016 (13) | 0.0007 (12) | 0.0005 (11) |
C2 | 0.0241 (15) | 0.0261 (14) | 0.0299 (13) | −0.0023 (12) | −0.0014 (12) | −0.0044 (11) |
C3 | 0.0214 (14) | 0.0206 (13) | 0.0286 (13) | 0.0021 (12) | −0.0017 (11) | 0.0010 (10) |
C4 | 0.0212 (14) | 0.0227 (13) | 0.0253 (12) | −0.0006 (12) | −0.0011 (11) | −0.0015 (10) |
C5 | 0.0223 (13) | 0.0166 (12) | 0.0275 (12) | 0.0000 (11) | −0.0027 (11) | −0.0027 (10) |
C6 | 0.0237 (14) | 0.0162 (12) | 0.0314 (13) | −0.0045 (11) | 0.0015 (11) | 0.0014 (10) |
C7 | 0.0367 (17) | 0.0390 (17) | 0.0323 (14) | −0.0131 (15) | 0.0072 (13) | −0.0114 (12) |
C8 | 0.060 (3) | 0.104 (3) | 0.0326 (17) | −0.010 (2) | −0.0050 (16) | −0.0175 (19) |
C9 | 0.069 (3) | 0.068 (2) | 0.057 (2) | 0.008 (2) | 0.026 (2) | −0.0138 (18) |
C10 | 0.0253 (15) | 0.0239 (14) | 0.0336 (14) | −0.0026 (12) | 0.0047 (12) | −0.0034 (11) |
C11 | 0.0311 (16) | 0.0294 (15) | 0.0405 (15) | −0.0054 (14) | 0.0017 (13) | −0.0075 (13) |
C12 | 0.0470 (19) | 0.0277 (15) | 0.0545 (18) | −0.0055 (16) | −0.0042 (16) | 0.0064 (13) |
C13 | 0.062 (2) | 0.0205 (15) | 0.0519 (18) | −0.0109 (16) | 0.0138 (17) | −0.0096 (13) |
O1—C7 | 1.429 (3) | C5—H5 | 1.0000 |
O1—C1 | 1.432 (3) | C6—H6 | 1.0000 |
O2—C7 | 1.423 (3) | C7—C9 | 1.502 (5) |
O2—C2 | 1.430 (3) | C7—C8 | 1.512 (4) |
O3—C3 | 1.428 (3) | C8—H8A | 0.9800 |
O3—C13 | 1.429 (3) | C8—H8B | 0.9800 |
O4—C4 | 1.425 (3) | C8—H8C | 0.9800 |
O4—H4O | 0.86 (3) | C9—H9A | 0.9800 |
O5—C10 | 1.426 (3) | C9—H9B | 0.9800 |
O5—C5 | 1.433 (3) | C9—H9C | 0.9800 |
O6—C6 | 1.433 (3) | C10—C11 | 1.515 (4) |
O6—C10 | 1.451 (3) | C10—C12 | 1.516 (4) |
C1—C6 | 1.517 (3) | C11—H11A | 0.9800 |
C1—C2 | 1.542 (4) | C11—H11B | 0.9800 |
C1—H1 | 1.0000 | C11—H11C | 0.9800 |
C2—C3 | 1.524 (3) | C12—H12A | 0.9800 |
C2—H2 | 1.0000 | C12—H12B | 0.9800 |
C3—C4 | 1.539 (3) | C12—H12C | 0.9800 |
C3—H3 | 1.0000 | C13—H13A | 0.9800 |
C4—C5 | 1.519 (3) | C13—H13B | 0.9800 |
C4—H4 | 1.0000 | C13—H13C | 0.9800 |
C5—C6 | 1.535 (4) | ||
C7—O1—C1 | 108.9 (2) | O2—C7—O1 | 104.05 (19) |
C7—O2—C2 | 107.0 (2) | O2—C7—C9 | 109.0 (3) |
C3—O3—C13 | 114.1 (2) | O1—C7—C9 | 108.7 (3) |
C4—O4—H4O | 105.6 (19) | O2—C7—C8 | 111.8 (2) |
C10—O5—C5 | 106.60 (19) | O1—C7—C8 | 109.7 (3) |
C6—O6—C10 | 109.51 (18) | C9—C7—C8 | 113.2 (2) |
O1—C1—C6 | 109.1 (2) | C7—C8—H8A | 109.5 |
O1—C1—C2 | 104.40 (19) | C7—C8—H8B | 109.5 |
C6—C1—C2 | 112.85 (19) | H8A—C8—H8B | 109.5 |
O1—C1—H1 | 110.1 | C7—C8—H8C | 109.5 |
C6—C1—H1 | 110.1 | H8A—C8—H8C | 109.5 |
C2—C1—H1 | 110.1 | H8B—C8—H8C | 109.5 |
O2—C2—C3 | 110.4 (2) | C7—C9—H9A | 109.5 |
O2—C2—C1 | 103.21 (19) | C7—C9—H9B | 109.5 |
C3—C2—C1 | 114.9 (2) | H9A—C9—H9B | 109.5 |
O2—C2—H2 | 109.4 | C7—C9—H9C | 109.5 |
C3—C2—H2 | 109.4 | H9A—C9—H9C | 109.5 |
C1—C2—H2 | 109.4 | H9B—C9—H9C | 109.5 |
O3—C3—C2 | 111.4 (2) | O5—C10—O6 | 105.6 (2) |
O3—C3—C4 | 107.26 (19) | O5—C10—C11 | 111.8 (2) |
C2—C3—C4 | 108.1 (2) | O6—C10—C11 | 108.8 (2) |
O3—C3—H3 | 110.0 | O5—C10—C12 | 107.5 (2) |
C2—C3—H3 | 110.0 | O6—C10—C12 | 109.1 (2) |
C4—C3—H3 | 110.0 | C11—C10—C12 | 113.8 (2) |
O4—C4—C5 | 112.6 (2) | C10—C11—H11A | 109.5 |
O4—C4—C3 | 111.83 (19) | C10—C11—H11B | 109.5 |
C5—C4—C3 | 109.8 (2) | H11A—C11—H11B | 109.5 |
O4—C4—H4 | 107.5 | C10—C11—H11C | 109.5 |
C5—C4—H4 | 107.5 | H11A—C11—H11C | 109.5 |
C3—C4—H4 | 107.5 | H11B—C11—H11C | 109.5 |
O5—C5—C4 | 110.3 (2) | C10—C12—H12A | 109.5 |
O5—C5—C6 | 103.00 (19) | C10—C12—H12B | 109.5 |
C4—C5—C6 | 115.2 (2) | H12A—C12—H12B | 109.5 |
O5—C5—H5 | 109.4 | C10—C12—H12C | 109.5 |
C4—C5—H5 | 109.4 | H12A—C12—H12C | 109.5 |
C6—C5—H5 | 109.4 | H12B—C12—H12C | 109.5 |
O6—C6—C1 | 112.0 (2) | O3—C13—H13A | 109.5 |
O6—C6—C5 | 103.28 (19) | O3—C13—H13B | 109.5 |
C1—C6—C5 | 112.8 (2) | H13A—C13—H13B | 109.5 |
O6—C6—H6 | 109.5 | O3—C13—H13C | 109.5 |
C1—C6—H6 | 109.5 | H13A—C13—H13C | 109.5 |
C5—C6—H6 | 109.5 | H13B—C13—H13C | 109.5 |
C7—O1—C1—C6 | −129.3 (2) | C3—C4—C5—C6 | −30.7 (3) |
C7—O1—C1—C2 | −8.5 (3) | C10—O6—C6—C1 | −110.0 (2) |
C7—O2—C2—C3 | 153.8 (2) | C10—O6—C6—C5 | 11.6 (2) |
C7—O2—C2—C1 | 30.6 (3) | O1—C1—C6—O6 | −77.1 (3) |
O1—C1—C2—O2 | −13.3 (3) | C2—C1—C6—O6 | 167.4 (2) |
C6—C1—C2—O2 | 105.0 (2) | O1—C1—C6—C5 | 166.95 (19) |
O1—C1—C2—C3 | −133.5 (2) | C2—C1—C6—C5 | 51.4 (3) |
C6—C1—C2—C3 | −15.2 (3) | O5—C5—C6—O6 | −28.4 (2) |
C13—O3—C3—C2 | −78.8 (3) | C4—C5—C6—O6 | −148.5 (2) |
C13—O3—C3—C4 | 163.0 (2) | O5—C5—C6—C1 | 92.7 (2) |
O2—C2—C3—O3 | 83.8 (3) | C4—C5—C6—C1 | −27.4 (3) |
C1—C2—C3—O3 | −160.0 (2) | C2—O2—C7—O1 | −36.4 (3) |
O2—C2—C3—C4 | −158.5 (2) | C2—O2—C7—C9 | −152.2 (2) |
C1—C2—C3—C4 | −42.4 (3) | C2—O2—C7—C8 | 81.9 (3) |
O3—C3—C4—O4 | −47.7 (3) | C1—O1—C7—O2 | 27.3 (3) |
C2—C3—C4—O4 | −168.0 (2) | C1—O1—C7—C9 | 143.3 (2) |
O3—C3—C4—C5 | −173.41 (18) | C1—O1—C7—C8 | −92.5 (3) |
C2—C3—C4—C5 | 66.3 (3) | C5—O5—C10—O6 | −28.6 (2) |
C10—O5—C5—C4 | 158.79 (18) | C5—O5—C10—C11 | 89.5 (2) |
C10—O5—C5—C6 | 35.3 (2) | C5—O5—C10—C12 | −145.0 (2) |
O4—C4—C5—O5 | 88.0 (2) | C6—O6—C10—O5 | 9.6 (3) |
C3—C4—C5—O5 | −146.8 (2) | C6—O6—C10—C11 | −110.5 (2) |
O4—C4—C5—C6 | −156.0 (2) | C6—O6—C10—C12 | 124.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4O···O3i | 0.87 (3) | 2.03 (3) | 2.855 (2) | 160 (3) |
C3—H3···O4i | 1.0 | 2.53 | 3.373 (3) | 141 |
C6—H6···O3ii | 1.0 | 2.54 | 3.530 (3) | 169 |
C13—H13C···O2 | 0.98 | 2.52 | 3.112 (4) | 118 |
Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x−1, y, z. |