Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805018520/wk6054sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805018520/wk6054Isup2.hkl |
CCDC reference: 277803
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and SADABS (Sheldrick, 2002); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2004 or? 2005); software used to prepare material for publication: SHELXTL.
C16H20O7 | F(000) = 688 |
Mr = 324.32 | Dx = 1.376 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5729 reflections |
a = 5.5771 (1) Å | θ = 1.8–25.4° |
b = 14.6164 (3) Å | µ = 0.11 mm−1 |
c = 19.2112 (4) Å | T = 173 K |
V = 1566.04 (5) Å3 | Needle, colourless |
Z = 4 | 1.00 × 0.06 × 0.04 mm |
Siemens SMART CCD area-detector diffractometer | 1700 independent reflections |
Radiation source: fine-focus sealed tube | 1306 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
ω scans | θmax = 25.4°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −6→6 |
Tmin = 0.766, Tmax = 0.996 | k = −17→17 |
17488 measured reflections | l = −23→23 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.0461P)2 + 0.7147P] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
1700 reflections | Δρmax = 0.19 e Å−3 |
244 parameters | Δρmin = −0.19 e Å−3 |
26 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.014 (2) |
Experimental. Data were collected at low temperature using a Siemens SMART CCD diffractometer equiped with a LT-2 device. A full sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal–to–detector distance of 3.97 cm, 20 s per frame. Preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). The collected frames were integrated using the preliminary orientation matrix which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 5729 reflections with I>10σ(I) after integration of all the frames data using SAINT (Siemens, 1995). |
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) | |
C1 | 0.6775 (6) | 0.9536 (2) | 0.8001 (2) | 0.0430 (9) | |
H1A | 0.7957 | 0.9610 | 0.8381 | 0.052* | |
H1B | 0.7570 | 0.9231 | 0.7603 | 0.052* | |
O1A | 0.5848 (8) | 1.0386 (3) | 0.7800 (4) | 0.0485 (17) | 0.50 |
O1B | 0.5893 (8) | 1.0101 (4) | 0.7434 (3) | 0.0457 (16) | 0.50 |
O2 | 0.2659 (4) | 0.95327 (14) | 0.80672 (12) | 0.0372 (6) | |
O3 | 0.4352 (4) | 0.96379 (14) | 0.93888 (12) | 0.0406 (6) | |
O4 | 0.2831 (7) | 0.7950 (2) | 0.99338 (15) | 0.0701 (9) | |
H4 | 0.1503 | 0.7812 | 1.0111 | 0.105* | |
O5 | 0.4404 (6) | 0.67468 (17) | 0.89191 (17) | 0.0720 (9) | |
H5 | 0.4151 | 0.6484 | 0.9301 | 0.108* | |
O6 | 0.4647 (5) | 0.81483 (14) | 0.78726 (13) | 0.0478 (7) | |
O7 | 0.7761 (5) | 0.94053 (17) | 0.99800 (13) | 0.0513 (7) | |
C2 | 0.4640 (6) | 0.8984 (2) | 0.82457 (18) | 0.0369 (8) | |
C3 | 0.4578 (7) | 0.8776 (2) | 0.90163 (18) | 0.0403 (9) | |
H3 | 0.6109 | 0.8469 | 0.9155 | 0.048* | |
C4 | 0.2499 (8) | 0.8181 (2) | 0.9221 (2) | 0.0509 (10) | |
H4A | 0.0969 | 0.8530 | 0.9165 | 0.061* | |
C5 | 0.2442 (8) | 0.7328 (2) | 0.8760 (2) | 0.0575 (11) | |
H5A | 0.0911 | 0.6990 | 0.8843 | 0.069* | |
C6 | 0.2579 (8) | 0.7596 (2) | 0.8012 (2) | 0.0562 (11) | |
H6A | 0.2642 | 0.7038 | 0.7721 | 0.067* | |
H6B | 0.1116 | 0.7940 | 0.7884 | 0.067* | |
C7 | 0.3404 (6) | 1.0237 (2) | 0.75889 (18) | 0.0408 (9) | |
C8A | 0.210 (3) | 1.1084 (10) | 0.7802 (16) | 0.050 (5) | 0.50 |
H8A1 | 0.2377 | 1.1200 | 0.8298 | 0.075* | 0.50 |
H8A2 | 0.0381 | 1.1005 | 0.7718 | 0.075* | 0.50 |
H8A3 | 0.2693 | 1.1604 | 0.7529 | 0.075* | 0.50 |
C8B | 0.287 (3) | 1.1155 (9) | 0.7892 (13) | 0.045 (4) | 0.50 |
H8B1 | 0.3775 | 1.1234 | 0.8325 | 0.068* | 0.50 |
H8B2 | 0.1148 | 1.1201 | 0.7991 | 0.068* | 0.50 |
H8B3 | 0.3328 | 1.1633 | 0.7560 | 0.068* | 0.50 |
C9A | 0.309 (3) | 0.9888 (12) | 0.6864 (5) | 0.067 (5) | 0.50 |
H9A1 | 0.3684 | 1.0343 | 0.6533 | 0.100* | 0.50 |
H9A2 | 0.1379 | 0.9775 | 0.6777 | 0.100* | 0.50 |
H9A3 | 0.3982 | 0.9316 | 0.6808 | 0.100* | 0.50 |
C9B | 0.217 (2) | 1.0146 (11) | 0.6900 (4) | 0.054 (4) | 0.50 |
H9B1 | 0.2824 | 1.0596 | 0.6573 | 0.082* | 0.50 |
H9B2 | 0.0444 | 1.0254 | 0.6960 | 0.082* | 0.50 |
H9B3 | 0.2421 | 0.9528 | 0.6716 | 0.082* | 0.50 |
C10 | 0.5971 (6) | 0.9849 (2) | 0.98769 (18) | 0.0366 (8) | |
C11 | 0.5340 (7) | 1.0692 (2) | 1.02623 (17) | 0.0361 (8) | |
C12 | 0.6892 (7) | 1.0999 (2) | 1.07759 (18) | 0.0425 (9) | |
H12 | 0.8338 | 1.0677 | 1.0865 | 0.051* | |
C13 | 0.6345 (7) | 1.1771 (2) | 1.1158 (2) | 0.0493 (10) | |
H13 | 0.7409 | 1.1977 | 1.1511 | 0.059* | |
C14 | 0.4253 (7) | 1.2244 (2) | 1.10268 (18) | 0.0456 (10) | |
H14 | 0.3874 | 1.2775 | 1.1290 | 0.055* | |
C15 | 0.2719 (7) | 1.1949 (2) | 1.05165 (17) | 0.0408 (8) | |
H15 | 0.1295 | 1.2284 | 1.0423 | 0.049* | |
C16 | 0.3222 (7) | 1.1166 (2) | 1.01348 (17) | 0.0377 (9) | |
H16 | 0.2132 | 1.0956 | 0.9790 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0277 (18) | 0.045 (2) | 0.057 (2) | 0.0006 (16) | 0.0070 (17) | −0.0009 (19) |
O1A | 0.032 (3) | 0.019 (3) | 0.095 (5) | 0.001 (2) | 0.014 (3) | −0.015 (3) |
O1B | 0.027 (3) | 0.029 (3) | 0.081 (4) | 0.001 (2) | 0.021 (3) | 0.010 (3) |
O2 | 0.0258 (12) | 0.0309 (12) | 0.0549 (14) | −0.0009 (11) | 0.0071 (12) | 0.0023 (11) |
O3 | 0.0462 (14) | 0.0260 (11) | 0.0496 (14) | 0.0037 (12) | −0.0029 (13) | −0.0029 (10) |
O4 | 0.088 (2) | 0.0422 (14) | 0.080 (2) | −0.0008 (17) | 0.024 (2) | 0.0140 (14) |
O5 | 0.079 (2) | 0.0286 (13) | 0.108 (2) | 0.0099 (16) | 0.002 (2) | 0.0002 (14) |
O6 | 0.0448 (14) | 0.0300 (12) | 0.0688 (16) | 0.0008 (12) | 0.0040 (14) | −0.0137 (12) |
O7 | 0.0424 (15) | 0.0523 (15) | 0.0592 (16) | 0.0115 (15) | −0.0001 (14) | −0.0041 (13) |
C2 | 0.0292 (18) | 0.0237 (16) | 0.058 (2) | 0.0026 (15) | 0.0056 (18) | −0.0066 (15) |
C3 | 0.0377 (19) | 0.0205 (15) | 0.063 (2) | 0.0034 (16) | 0.0014 (19) | −0.0014 (15) |
C4 | 0.051 (2) | 0.0285 (17) | 0.073 (3) | −0.0030 (19) | 0.012 (2) | 0.0078 (17) |
C5 | 0.050 (2) | 0.0233 (17) | 0.099 (3) | −0.0075 (19) | 0.007 (3) | −0.0018 (19) |
C6 | 0.045 (2) | 0.0325 (18) | 0.091 (3) | −0.0042 (19) | −0.004 (3) | −0.015 (2) |
C7 | 0.0306 (18) | 0.0286 (17) | 0.063 (2) | −0.0036 (15) | 0.0060 (17) | −0.0015 (17) |
C8A | 0.042 (9) | 0.035 (6) | 0.073 (10) | −0.006 (5) | −0.012 (8) | 0.001 (5) |
C8B | 0.050 (10) | 0.028 (5) | 0.057 (9) | −0.002 (6) | 0.015 (9) | −0.001 (4) |
C9A | 0.105 (13) | 0.053 (9) | 0.043 (6) | −0.022 (7) | 0.035 (6) | −0.023 (4) |
C9B | 0.071 (9) | 0.050 (9) | 0.042 (6) | −0.017 (6) | 0.026 (5) | −0.013 (4) |
C10 | 0.037 (2) | 0.0337 (18) | 0.0389 (19) | −0.0035 (17) | 0.0041 (17) | 0.0072 (15) |
C11 | 0.0397 (19) | 0.0297 (16) | 0.0389 (18) | −0.0029 (17) | 0.0050 (17) | 0.0048 (14) |
C12 | 0.032 (2) | 0.045 (2) | 0.051 (2) | −0.0027 (17) | −0.0002 (18) | 0.0015 (17) |
C13 | 0.047 (2) | 0.046 (2) | 0.056 (2) | −0.010 (2) | −0.003 (2) | −0.0064 (19) |
C14 | 0.049 (2) | 0.0369 (18) | 0.051 (2) | −0.009 (2) | 0.008 (2) | −0.0095 (16) |
C15 | 0.040 (2) | 0.0321 (17) | 0.051 (2) | 0.0015 (17) | −0.0010 (19) | −0.0001 (15) |
C16 | 0.042 (2) | 0.0327 (17) | 0.0383 (19) | −0.0057 (16) | 0.0001 (17) | 0.0009 (15) |
C1—O1A | 1.400 (5) | C7—C8A | 1.493 (6) |
C1—O1B | 1.452 (5) | C7—C8B | 1.493 (6) |
C1—C2 | 1.514 (5) | C7—C9B | 1.499 (6) |
C1—H1A | 0.9900 | C8A—H8A1 | 0.9800 |
C1—H1B | 0.9900 | C8A—H8A2 | 0.9800 |
O1A—C7 | 1.438 (5) | C8A—H8A3 | 0.9800 |
O1B—C7 | 1.433 (5) | C8B—H8B1 | 0.9800 |
O2—C2 | 1.407 (4) | C8B—H8B2 | 0.9800 |
O2—C7 | 1.441 (4) | C8B—H8B3 | 0.9800 |
O3—C10 | 1.338 (4) | C9A—H9A1 | 0.9800 |
O3—C3 | 1.455 (4) | C9A—H9A2 | 0.9800 |
O4—C4 | 1.423 (5) | C9A—H9A3 | 0.9800 |
O4—H4 | 0.8400 | C9B—H9B1 | 0.9800 |
O5—C5 | 1.419 (5) | C9B—H9B2 | 0.9800 |
O5—H5 | 0.8400 | C9B—H9B3 | 0.9800 |
O6—C2 | 1.417 (4) | C10—C11 | 1.481 (5) |
O6—C6 | 1.433 (5) | C11—C16 | 1.391 (5) |
O7—C10 | 1.207 (4) | C11—C12 | 1.387 (5) |
C2—C3 | 1.512 (5) | C12—C13 | 1.381 (5) |
C3—C4 | 1.501 (5) | C12—H12 | 0.9500 |
C3—H3 | 1.0000 | C13—C14 | 1.379 (6) |
C4—C5 | 1.530 (5) | C13—H13 | 0.9500 |
C4—H4A | 1.0000 | C14—C15 | 1.371 (5) |
C5—C6 | 1.491 (6) | C14—H14 | 0.9500 |
C5—H5A | 1.0000 | C15—C16 | 1.388 (5) |
C6—H6A | 0.9900 | C15—H15 | 0.9500 |
C6—H6B | 0.9900 | C16—H16 | 0.9500 |
C7—C9A | 1.493 (6) | ||
O1A—C1—C2 | 105.5 (3) | O2—C7—C8A | 106.1 (12) |
O1B—C1—C2 | 105.6 (3) | C9A—C7—C8A | 118.8 (12) |
O1A—C1—H1A | 110.6 | O1A—C7—C8A | 105.0 (7) |
C2—C1—H1A | 110.6 | O1B—C7—C8B | 113.6 (8) |
O1A—C1—H1B | 110.6 | O2—C7—C8B | 109.6 (11) |
C2—C1—H1B | 110.6 | O1B—C7—C9B | 104.5 (6) |
H1A—C1—H1B | 108.8 | O2—C7—C9B | 111.5 (8) |
C1—O1A—C7 | 107.0 (4) | C8B—C7—C9B | 109.4 (11) |
C7—O1B—C1 | 104.6 (3) | C7—C8A—H8A1 | 109.5 |
C2—O2—C7 | 109.6 (2) | C7—C8A—H8A2 | 109.5 |
C10—O3—C3 | 119.0 (3) | C7—C8A—H8A3 | 109.5 |
C4—O4—H4 | 109.5 | C7—C8B—H8B1 | 109.5 |
C5—O5—H5 | 109.5 | C7—C8B—H8B2 | 109.5 |
C2—O6—C6 | 112.9 (3) | H8B1—C8B—H8B2 | 109.5 |
O2—C2—O6 | 111.7 (3) | C7—C8B—H8B3 | 109.5 |
O2—C2—C1 | 103.8 (2) | H8B1—C8B—H8B3 | 109.5 |
O6—C2—C1 | 107.5 (3) | H8B2—C8B—H8B3 | 109.5 |
O2—C2—C3 | 109.6 (3) | C7—C9A—H9A1 | 109.5 |
O6—C2—C3 | 108.7 (3) | C7—C9A—H9A2 | 109.5 |
C1—C2—C3 | 115.5 (3) | C7—C9A—H9A3 | 109.5 |
O3—C3—C4 | 107.8 (3) | C7—C9B—H9B1 | 109.5 |
O3—C3—C2 | 108.0 (2) | C7—C9B—H9B2 | 109.5 |
C4—C3—C2 | 113.0 (3) | H9B1—C9B—H9B2 | 109.5 |
O3—C3—H3 | 109.3 | C7—C9B—H9B3 | 109.5 |
C4—C3—H3 | 109.3 | H9B1—C9B—H9B3 | 109.5 |
C2—C3—H3 | 109.3 | H9B2—C9B—H9B3 | 109.5 |
O4—C4—C3 | 106.8 (3) | O7—C10—O3 | 123.4 (3) |
O4—C4—C5 | 111.5 (3) | O7—C10—C11 | 124.2 (3) |
C3—C4—C5 | 109.7 (3) | O3—C10—C11 | 112.4 (3) |
O4—C4—H4A | 109.6 | C16—C11—C12 | 119.6 (3) |
C3—C4—H4A | 109.6 | C16—C11—C10 | 121.9 (3) |
C5—C4—H4A | 109.6 | C12—C11—C10 | 118.5 (3) |
O5—C5—C6 | 109.0 (4) | C13—C12—C11 | 120.3 (4) |
O5—C5—C4 | 110.3 (4) | C13—C12—H12 | 119.8 |
C6—C5—C4 | 110.0 (3) | C11—C12—H12 | 119.8 |
O5—C5—H5A | 109.2 | C14—C13—C12 | 119.9 (4) |
C6—C5—H5A | 109.2 | C14—C13—H13 | 120.0 |
C4—C5—H5A | 109.2 | C12—C13—H13 | 120.0 |
O6—C6—C5 | 111.7 (3) | C13—C14—C15 | 120.1 (3) |
O6—C6—H6A | 109.3 | C13—C14—H14 | 120.0 |
C5—C6—H6A | 109.3 | C15—C14—H14 | 120.0 |
O6—C6—H6B | 109.3 | C16—C15—C14 | 120.8 (4) |
C5—C6—H6B | 109.3 | C16—C15—H15 | 119.6 |
H6A—C6—H6B | 107.9 | C14—C15—H15 | 119.6 |
O1B—C7—O2 | 108.2 (3) | C15—C16—C11 | 119.3 (3) |
O2—C7—C9A | 108.4 (8) | C15—C16—H16 | 120.4 |
O2—C7—O1A | 101.7 (3) | C11—C16—H16 | 120.4 |
C9A—C7—O1A | 115.3 (8) | ||
C2—C1—O1A—C7 | −27.5 (5) | C2—O6—C6—C5 | −61.8 (4) |
C2—C1—O1B—C7 | 28.3 (5) | O5—C5—C6—O6 | −65.6 (4) |
C7—O2—C2—O6 | −101.1 (3) | C4—C5—C6—O6 | 55.5 (5) |
C7—O2—C2—C1 | 14.4 (3) | C1—O1B—C7—O2 | −19.8 (5) |
C7—O2—C2—C3 | 138.3 (3) | C1—O1B—C7—C8B | 102.1 (12) |
C6—O6—C2—O2 | −61.4 (4) | C1—O1B—C7—C9B | −138.7 (8) |
C6—O6—C2—C1 | −174.7 (3) | C2—O2—C7—O1B | 3.0 (4) |
C6—O6—C2—C3 | 59.7 (4) | C2—O2—C7—C9A | 91.3 (7) |
O1A—C1—C2—O2 | 8.0 (4) | C2—O2—C7—O1A | −30.6 (4) |
O1B—C1—C2—O2 | −26.5 (4) | C2—O2—C7—C8A | −140.1 (8) |
O1A—C1—C2—O6 | 126.5 (4) | C2—O2—C7—C8B | −121.3 (8) |
O1B—C1—C2—O6 | 92.0 (4) | C2—O2—C7—C9B | 117.4 (6) |
O1A—C1—C2—C3 | −112.0 (4) | C1—O1A—C7—O2 | 35.5 (5) |
O1B—C1—C2—C3 | −146.5 (4) | C1—O1A—C7—C9A | −81.5 (9) |
C10—O3—C3—C4 | 112.8 (3) | C1—O1A—C7—C8A | 145.9 (14) |
C10—O3—C3—C2 | −124.8 (3) | C3—O3—C10—O7 | 7.8 (5) |
O2—C2—C3—O3 | −52.5 (4) | C3—O3—C10—C11 | −173.4 (3) |
O6—C2—C3—O3 | −174.9 (3) | O7—C10—C11—C16 | −178.4 (3) |
C1—C2—C3—O3 | 64.2 (4) | O3—C10—C11—C16 | 2.8 (4) |
O2—C2—C3—C4 | 66.6 (3) | O7—C10—C11—C12 | 0.0 (5) |
O6—C2—C3—C4 | −55.8 (4) | O3—C10—C11—C12 | −178.8 (3) |
C1—C2—C3—C4 | −176.6 (3) | C16—C11—C12—C13 | −0.1 (5) |
O3—C3—C4—O4 | −67.8 (3) | C10—C11—C12—C13 | −178.6 (3) |
C2—C3—C4—O4 | 173.0 (3) | C11—C12—C13—C14 | −0.4 (5) |
O3—C3—C4—C5 | 171.3 (3) | C12—C13—C14—C15 | −0.1 (5) |
C2—C3—C4—C5 | 52.0 (4) | C13—C14—C15—C16 | 1.1 (5) |
O4—C4—C5—O5 | −48.6 (5) | C14—C15—C16—C11 | −1.6 (5) |
C3—C4—C5—O5 | 69.5 (4) | C12—C11—C16—C15 | 1.1 (5) |
O4—C4—C5—C6 | −168.9 (4) | C10—C11—C16—C15 | 179.5 (3) |
C3—C4—C5—C6 | −50.8 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O4i | 0.84 | 2.33 | 3.093 (5) | 151 |
O4—H4···O5i | 0.84 | 2.29 | 2.951 (5) | 136 |
O5—H5···O4ii | 0.84 | 2.66 | 2.951 (5) | 102 |
O5—H5···O7i | 0.84 | 2.05 | 2.855 (4) | 160 |
C3—H3···O7 | 1.00 | 2.29 | 2.725 (5) | 105 |
C9A—H9A1···O5iii | 0.98 | 2.47 | 3.41 (2) | 160 |
Symmetry codes: (i) x−1/2, −y+3/2, −z+2; (ii) x+1/2, −y+3/2, −z+2; (iii) −x+1, y+1/2, −z+3/2. |