Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600576715018233/ks5484sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600576715018233/ks5484Isup2.hkl | |
Zip compressed file https://doi.org/10.1107/S1600576715018233/ks5484sup3.zip | |
Zip compressed file https://doi.org/10.1107/S1600576715018233/ks5484sup4.zip | |
Portable Document Format (PDF) file https://doi.org/10.1107/S1600576715018233/ks5484sup5.pdf |
CCDC reference: 1428622
Cell refinement: SAINT v8.27A (Bruker, 2012); data reduction: SAINT v8.27A (Bruker, 2012); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL (Sheldrick, 2008); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).
C12H22O11 | F(000) = 364 |
Mr = 342.29 | Dx = 1.587 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.7630 (1) Å | Cell parameters from 9946 reflections |
b = 8.7109 (1) Å | θ = 2.7–37.7° |
c = 10.8701 (1) Å | µ = 0.14 mm−1 |
β = 102.937 (1)° | T = 298 K |
V = 716.41 (1) Å3 | Prism, colourless |
Z = 2 | 0.2 × 0.2 × 0.1 mm |
Bruker APEX-II CCD diffractometer | 16720 independent reflections |
Graphite monochromator | 10732 reflections with I > 2σ(I) |
Detector resolution: 7.9 pixels mm-1 | Rint = 0.053 |
ω and φ scans | θmax = 52.9°, θmin = 1.9° |
Absorption correction: multi-scan SADABS2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0783 before and 0.0581 after correction. The Ratio of minimum to maximum transmission is 0.9421. The λ/2 correction factor is 0.0015. | h = −17→17 |
Tmin = 0.814, Tmax = 0.864 | k = −19→19 |
85318 measured reflections | l = −24→24 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.041 | w = 1/[σ2(Fo2) + (0.0554P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.110 | (Δ/σ)max = 0.001 |
S = 0.97 | Δρmax = 0.42 e Å−3 |
16720 reflections | Δρmin = −0.27 e Å−3 |
240 parameters | Absolute structure: Flack x determined using 3930 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
1 restraint | Absolute structure parameter: 0.10 (17) |
Primary atom site location: iterative |
C12H22O11 | V = 716.41 (1) Å3 |
Mr = 342.29 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 7.7630 (1) Å | µ = 0.14 mm−1 |
b = 8.7109 (1) Å | T = 298 K |
c = 10.8701 (1) Å | 0.2 × 0.2 × 0.1 mm |
β = 102.937 (1)° |
Bruker APEX-II CCD diffractometer | 16720 independent reflections |
Absorption correction: multi-scan SADABS2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0783 before and 0.0581 after correction. The Ratio of minimum to maximum transmission is 0.9421. The λ/2 correction factor is 0.0015. | 10732 reflections with I > 2σ(I) |
Tmin = 0.814, Tmax = 0.864 | Rint = 0.053 |
85318 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.110 | Δρmax = 0.42 e Å−3 |
S = 0.97 | Δρmin = −0.27 e Å−3 |
16720 reflections | Absolute structure: Flack x determined using 3930 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
240 parameters | Absolute structure parameter: 0.10 (17) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
O5 | 0.36841 (9) | 0.35614 (8) | 0.87745 (6) | 0.01993 (10) | |
O1 | 0.39132 (8) | 0.40800 (7) | 0.67129 (5) | 0.01663 (8) | |
O2' | 0.31604 (8) | 0.66041 (8) | 0.71222 (6) | 0.02006 (10) | |
O2 | 0.74756 (10) | 0.31907 (10) | 0.72915 (7) | 0.02551 (13) | |
O3' | 0.20423 (10) | 0.43686 (9) | 0.42597 (6) | 0.02336 (12) | |
C1 | 0.48497 (10) | 0.39692 (9) | 0.79987 (7) | 0.01652 (10) | |
H1 | 0.5361 | 0.4976 | 0.8269 | 0.020* | |
C2' | 0.36918 (9) | 0.56218 (9) | 0.62442 (7) | 0.01536 (10) | |
O4' | −0.08937 (9) | 0.65786 (11) | 0.47835 (7) | 0.02704 (14) | |
O1' | 0.62086 (10) | 0.51904 (11) | 0.52977 (7) | 0.02675 (13) | |
O6' | 0.03985 (11) | 0.51644 (12) | 0.82653 (8) | 0.03054 (15) | |
C3' | 0.21469 (10) | 0.56404 (9) | 0.50718 (7) | 0.01667 (10) | |
H3'A | 0.2277 | 0.6561 | 0.4582 | 0.020* | |
O6 | 0.28608 (13) | 0.20923 (12) | 1.08175 (8) | 0.03221 (16) | |
C2 | 0.63601 (11) | 0.28017 (10) | 0.81255 (7) | 0.01893 (12) | |
H2A | 0.7066 | 0.2837 | 0.8994 | 0.023* | |
C5' | 0.12857 (10) | 0.69352 (10) | 0.67634 (8) | 0.01922 (12) | |
H5' | 0.1127 | 0.8004 | 0.6479 | 0.023* | |
C5 | 0.29554 (12) | 0.20323 (10) | 0.85919 (8) | 0.02092 (13) | |
H5 | 0.2191 | 0.1951 | 0.7745 | 0.025* | |
O3 | 0.70323 (14) | 0.00683 (11) | 0.80871 (9) | 0.03492 (19) | |
C3 | 0.56427 (13) | 0.11799 (10) | 0.78547 (8) | 0.02144 (13) | |
H3A | 0.4980 | 0.1106 | 0.6976 | 0.026* | |
C4' | 0.05477 (10) | 0.58827 (10) | 0.56467 (7) | 0.01792 (11) | |
H4'A | 0.0176 | 0.4903 | 0.5947 | 0.022* | |
C1' | 0.54373 (11) | 0.62374 (11) | 0.60298 (9) | 0.02158 (13) | |
H1'A | 0.5237 | 0.7217 | 0.5596 | 0.026* | |
H1'B | 0.6247 | 0.6404 | 0.6838 | 0.026* | |
C4 | 0.44218 (13) | 0.08372 (10) | 0.87418 (8) | 0.02258 (14) | |
H4 | 0.5111 | 0.0849 | 0.9615 | 0.027* | |
C6 | 0.18429 (14) | 0.18419 (13) | 0.95757 (10) | 0.02785 (17) | |
H6A | 0.0868 | 0.2565 | 0.9400 | 0.033* | |
H6B | 0.1351 | 0.0814 | 0.9518 | 0.033* | |
C6' | 0.04663 (13) | 0.67307 (13) | 0.78920 (9) | 0.02666 (17) | |
H6'A | 0.1145 | 0.7315 | 0.8596 | 0.032* | |
H6'B | −0.0724 | 0.7144 | 0.7690 | 0.032* | |
O4 | 0.35558 (16) | −0.05938 (11) | 0.84910 (13) | 0.0415 (2) | |
H2 | 0.837 (3) | 0.375 (3) | 0.768 (2) | 0.050 (6)* | |
H3 | 0.735 (3) | −0.022 (3) | 0.746 (2) | 0.051 (6)* | |
H6' | 0.151 (3) | 0.483 (3) | 0.850 (2) | 0.053 (7)* | |
H6 | 0.283 (3) | 0.305 (3) | 1.099 (2) | 0.046 (6)* | |
H1' | 0.654 (3) | 0.448 (3) | 0.572 (2) | 0.040 (5)* | |
H4' | −0.179 (3) | 0.607 (3) | 0.487 (2) | 0.047 (6)* | |
H3' | 0.185 (3) | 0.361 (3) | 0.4618 (18) | 0.030 (4)* | |
H4A | 0.421 (5) | −0.119 (4) | 0.842 (3) | 0.080 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O5 | 0.0246 (3) | 0.0178 (2) | 0.0197 (2) | 0.00012 (19) | 0.00992 (19) | 0.00016 (18) |
O1 | 0.0190 (2) | 0.01404 (19) | 0.01625 (18) | −0.00084 (17) | 0.00274 (15) | 0.00062 (16) |
O2' | 0.0166 (2) | 0.0196 (2) | 0.0233 (2) | 0.00146 (18) | 0.00322 (17) | −0.0064 (2) |
O2 | 0.0201 (3) | 0.0300 (3) | 0.0282 (3) | 0.0008 (2) | 0.0093 (2) | 0.0025 (3) |
O3' | 0.0270 (3) | 0.0235 (3) | 0.0199 (2) | −0.0030 (2) | 0.0058 (2) | −0.0046 (2) |
C1 | 0.0181 (3) | 0.0159 (2) | 0.0157 (2) | −0.0002 (2) | 0.00409 (19) | −0.0002 (2) |
C2' | 0.0141 (2) | 0.0146 (2) | 0.0180 (2) | −0.00066 (19) | 0.00474 (18) | 0.0003 (2) |
O4' | 0.0161 (2) | 0.0332 (4) | 0.0300 (3) | 0.0030 (2) | 0.0013 (2) | 0.0076 (3) |
O1' | 0.0215 (3) | 0.0338 (4) | 0.0283 (3) | 0.0016 (3) | 0.0127 (2) | 0.0040 (3) |
O6' | 0.0260 (3) | 0.0352 (4) | 0.0329 (3) | 0.0002 (3) | 0.0117 (3) | 0.0068 (3) |
C3' | 0.0160 (2) | 0.0172 (3) | 0.0172 (2) | −0.0007 (2) | 0.00456 (19) | 0.0014 (2) |
O6 | 0.0428 (4) | 0.0337 (4) | 0.0238 (3) | 0.0067 (3) | 0.0152 (3) | 0.0049 (3) |
C2 | 0.0191 (3) | 0.0200 (3) | 0.0174 (2) | 0.0018 (2) | 0.0036 (2) | 0.0013 (2) |
C5' | 0.0171 (3) | 0.0181 (3) | 0.0232 (3) | 0.0021 (2) | 0.0062 (2) | −0.0006 (2) |
C5 | 0.0236 (3) | 0.0203 (3) | 0.0194 (3) | −0.0024 (3) | 0.0061 (2) | 0.0011 (2) |
O3 | 0.0498 (5) | 0.0266 (3) | 0.0342 (4) | 0.0186 (3) | 0.0218 (4) | 0.0099 (3) |
C3 | 0.0287 (4) | 0.0179 (3) | 0.0192 (3) | 0.0034 (3) | 0.0085 (3) | 0.0009 (2) |
C4' | 0.0149 (2) | 0.0193 (3) | 0.0197 (3) | 0.0002 (2) | 0.0041 (2) | 0.0017 (2) |
C1' | 0.0162 (3) | 0.0220 (3) | 0.0272 (3) | −0.0038 (2) | 0.0064 (2) | 0.0023 (3) |
C4 | 0.0299 (4) | 0.0161 (3) | 0.0237 (3) | −0.0008 (3) | 0.0101 (3) | 0.0006 (2) |
C6 | 0.0257 (4) | 0.0308 (4) | 0.0301 (4) | −0.0001 (3) | 0.0126 (3) | 0.0064 (3) |
C6' | 0.0253 (4) | 0.0302 (4) | 0.0276 (4) | 0.0024 (3) | 0.0126 (3) | −0.0032 (3) |
O4 | 0.0482 (5) | 0.0186 (3) | 0.0637 (6) | −0.0088 (3) | 0.0256 (5) | −0.0069 (4) |
O5—C1 | 1.4134 (9) | O6—H6 | 0.86 (3) |
O5—C5 | 1.4433 (11) | C2—H2A | 0.9800 |
O1—C1 | 1.4271 (9) | C2—C3 | 1.5229 (13) |
O1—C2' | 1.4330 (9) | C5'—H5' | 0.9800 |
O2'—C2' | 1.4105 (9) | C5'—C4' | 1.5267 (12) |
O2'—C5' | 1.4489 (10) | C5'—C6' | 1.5135 (12) |
O2—C2 | 1.4276 (11) | C5—H5 | 0.9800 |
O2—H2 | 0.87 (3) | C5—C4 | 1.5242 (13) |
O3'—C3' | 1.4075 (10) | C5—C6 | 1.5265 (12) |
O3'—H3' | 0.79 (2) | O3—C3 | 1.4293 (12) |
C1—H1 | 0.9800 | O3—H3 | 0.82 (3) |
C1—C2 | 1.5348 (11) | C3—H3A | 0.9800 |
C2'—C3' | 1.5423 (10) | C3—C4 | 1.5253 (12) |
C2'—C1' | 1.5230 (10) | C4'—H4'A | 0.9800 |
O4'—C4' | 1.4247 (10) | C1'—H1'A | 0.9700 |
O4'—H4' | 0.85 (2) | C1'—H1'B | 0.9700 |
O1'—C1' | 1.4272 (12) | C4—H4 | 0.9800 |
O1'—H1' | 0.78 (3) | C4—O4 | 1.4135 (13) |
O6'—C6' | 1.4278 (15) | C6—H6A | 0.9700 |
O6'—H6' | 0.89 (3) | C6—H6B | 0.9700 |
C3'—H3'A | 0.9800 | C6'—H6'A | 0.9700 |
C3'—C4' | 1.5244 (10) | C6'—H6'B | 0.9700 |
O6—C6 | 1.4200 (14) | O4—H4A | 0.74 (4) |
C1—O5—C5 | 115.69 (6) | C4—C5—H5 | 109.4 |
C1—O1—C2' | 113.94 (6) | C4—C5—C6 | 112.15 (7) |
C2'—O2'—C5' | 111.53 (6) | C6—C5—H5 | 109.4 |
C2—O2—H2 | 110.7 (16) | C3—O3—H3 | 114.6 (19) |
C3'—O3'—H3' | 109.6 (14) | C2—C3—H3A | 109.8 |
O5—C1—O1 | 110.34 (6) | C2—C3—C4 | 108.15 (7) |
O5—C1—H1 | 108.4 | O3—C3—C2 | 111.43 (9) |
O5—C1—C2 | 110.98 (6) | O3—C3—H3A | 109.8 |
O1—C1—H1 | 108.4 | O3—C3—C4 | 107.88 (7) |
O1—C1—C2 | 110.13 (6) | C4—C3—H3A | 109.8 |
C2—C1—H1 | 108.4 | O4'—C4'—C3' | 112.37 (7) |
O1—C2'—C3' | 108.23 (6) | O4'—C4'—C5' | 111.58 (7) |
O1—C2'—C1' | 110.15 (6) | O4'—C4'—H4'A | 110.1 |
O2'—C2'—O1 | 110.98 (6) | C3'—C4'—C5' | 102.36 (6) |
O2'—C2'—C3' | 105.16 (6) | C3'—C4'—H4'A | 110.1 |
O2'—C2'—C1' | 107.16 (6) | C5'—C4'—H4'A | 110.1 |
C1'—C2'—C3' | 115.07 (6) | C2'—C1'—H1'A | 109.4 |
C4'—O4'—H4' | 104.5 (17) | C2'—C1'—H1'B | 109.4 |
C1'—O1'—H1' | 107.4 (16) | O1'—C1'—C2' | 111.04 (7) |
C6'—O6'—H6' | 107.3 (19) | O1'—C1'—H1'A | 109.4 |
O3'—C3'—C2' | 115.78 (7) | O1'—C1'—H1'B | 109.4 |
O3'—C3'—H3'A | 107.6 | H1'A—C1'—H1'B | 108.0 |
O3'—C3'—C4' | 115.35 (7) | C5—C4—C3 | 110.71 (7) |
C2'—C3'—H3'A | 107.6 | C5—C4—H4 | 109.2 |
C4'—C3'—C2' | 102.52 (6) | C3—C4—H4 | 109.2 |
C4'—C3'—H3'A | 107.6 | O4—C4—C5 | 105.68 (9) |
C6—O6—H6 | 108.5 (16) | O4—C4—C3 | 112.75 (8) |
O2—C2—C1 | 110.21 (7) | O4—C4—H4 | 109.2 |
O2—C2—H2A | 108.5 | O6—C6—C5 | 111.56 (8) |
O2—C2—C3 | 110.18 (7) | O6—C6—H6A | 109.3 |
C1—C2—H2A | 108.5 | O6—C6—H6B | 109.3 |
C3—C2—C1 | 111.00 (7) | C5—C6—H6A | 109.3 |
C3—C2—H2A | 108.5 | C5—C6—H6B | 109.3 |
O2'—C5'—H5' | 108.8 | H6A—C6—H6B | 108.0 |
O2'—C5'—C4' | 105.66 (6) | O6'—C6'—C5' | 113.07 (8) |
O2'—C5'—C6' | 109.72 (7) | O6'—C6'—H6'A | 109.0 |
C4'—C5'—H5' | 108.8 | O6'—C6'—H6'B | 109.0 |
C6'—C5'—H5' | 108.8 | C5'—C6'—H6'A | 109.0 |
C6'—C5'—C4' | 115.01 (7) | C5'—C6'—H6'B | 109.0 |
O5—C5—H5 | 109.4 | H6'A—C6'—H6'B | 107.8 |
O5—C5—C4 | 110.81 (7) | C4—O4—H4A | 109 (3) |
O5—C5—C6 | 105.65 (8) | ||
O5—C1—C2—O2 | 177.24 (7) | C1—C2—C3—C4 | −56.04 (8) |
O5—C1—C2—C3 | 54.88 (8) | C2'—O1—C1—O5 | 108.00 (7) |
O5—C5—C4—C3 | −55.19 (9) | C2'—O1—C1—C2 | −129.14 (7) |
O5—C5—C4—O4 | −177.56 (8) | C2'—O2'—C5'—C4' | 8.07 (9) |
O5—C5—C6—O6 | −56.89 (10) | C2'—O2'—C5'—C6' | 132.61 (8) |
O1—C1—C2—O2 | 54.75 (9) | C2'—C3'—C4'—O4' | 154.83 (7) |
O1—C1—C2—C3 | −67.60 (8) | C2'—C3'—C4'—C5' | 35.01 (8) |
O1—C2'—C3'—O3' | −38.93 (8) | C3'—C2'—C1'—O1' | −72.06 (9) |
O1—C2'—C3'—C4' | 87.53 (7) | C2—C3—C4—C5 | 56.46 (9) |
O1—C2'—C1'—O1' | 50.60 (9) | C2—C3—C4—O4 | 174.61 (9) |
O2'—C2'—C3'—O3' | −157.60 (6) | C5'—O2'—C2'—O1 | −102.24 (7) |
O2'—C2'—C3'—C4' | −31.14 (8) | C5'—O2'—C2'—C3' | 14.57 (8) |
O2'—C2'—C1'—O1' | 171.41 (7) | C5'—O2'—C2'—C1' | 137.47 (7) |
O2'—C5'—C4'—O4' | −147.62 (7) | C5—O5—C1—O1 | 67.67 (8) |
O2'—C5'—C4'—C3' | −27.25 (8) | C5—O5—C1—C2 | −54.69 (9) |
O2'—C5'—C6'—O6' | −69.72 (10) | O3—C3—C4—C5 | 177.11 (8) |
O2—C2—C3—O3 | 63.18 (9) | O3—C3—C4—O4 | −64.74 (12) |
O2—C2—C3—C4 | −178.42 (7) | C4'—C5'—C6'—O6' | 49.21 (11) |
O3'—C3'—C4'—O4' | −78.43 (9) | C1'—C2'—C3'—O3' | 84.74 (9) |
O3'—C3'—C4'—C5' | 161.75 (7) | C1'—C2'—C3'—C4' | −148.80 (7) |
C1—O5—C5—C4 | 55.18 (9) | C4—C5—C6—O6 | 63.92 (11) |
C1—O5—C5—C6 | 176.86 (7) | C6—C5—C4—C3 | −172.97 (8) |
C1—O1—C2'—O2' | −44.86 (8) | C6—C5—C4—O4 | 64.65 (10) |
C1—O1—C2'—C3' | −159.77 (6) | C6'—C5'—C4'—O4' | 91.21 (9) |
C1—O1—C2'—C1' | 73.64 (8) | C6'—C5'—C4'—C3' | −148.42 (7) |
C1—C2—C3—O3 | −174.45 (6) |
Experimental details
Crystal data | |
Chemical formula | C12H22O11 |
Mr | 342.29 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 298 |
a, b, c (Å) | 7.7630 (1), 8.7109 (1), 10.8701 (1) |
β (°) | 102.937 (1) |
V (Å3) | 716.41 (1) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.14 |
Crystal size (mm) | 0.2 × 0.2 × 0.1 |
Data collection | |
Diffractometer | Bruker APEX-II CCD |
Absorption correction | Multi-scan SADABS2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0783 before and 0.0581 after correction. The Ratio of minimum to maximum transmission is 0.9421. The λ/2 correction factor is 0.0015. |
Tmin, Tmax | 0.814, 0.864 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 85318, 16720, 10732 |
Rint | 0.053 |
(sin θ/λ)max (Å−1) | 1.122 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.110, 0.97 |
No. of reflections | 16720 |
No. of parameters | 240 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.42, −0.27 |
Absolute structure | Flack x determined using 3930 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
Absolute structure parameter | 0.10 (17) |
Computer programs: SAINT v8.27A (Bruker, 2012), olex2.solve (Bourhis et al., 2015), SHELXL (Sheldrick, 2008), Olex2 (Dolomanov et al., 2009).