Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802018524/cf6216sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802018524/cf6216Isup2.hkl |
CCDC reference: 200762
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.007 Å
- R factor = 0.066
- wR factor = 0.171
- Data-to-parameter ratio = 11.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
C14H12O8 | F(000) = 320 |
Mr = 308.24 | Dx = 1.554 Mg m−3 |
Triclinic, P1 | Melting point: 130° c K |
a = 6.862 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.335 (1) Å | Cell parameters from 180 reflections |
c = 13.323 (3) Å | θ = 10.3–21.1° |
α = 80.73 (1)° | µ = 0.13 mm−1 |
β = 85.30 (1)° | T = 100 K |
γ = 86.60 (1)° | Needle, colourless |
V = 658.9 (2) Å3 | 0.40 × 0.06 × 0.02 mm |
Z = 2 |
SMART 1K CCD area-detector diffractometer | 1173 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.094 |
Graphite monochromator | θmax = 25.1°, θmin = 1.6° |
Detector resolution: 8 pixels mm-1 | h = −8→7 |
ω scans | k = −8→8 |
3856 measured reflections | l = −15→14 |
2328 independent 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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.171 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0618P)2] where P = (Fo2 + 2Fc2)/3 |
2328 reflections | (Δ/σ)max < 0.001 |
207 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
Experimental. The data collection nominally covered more than a hemisphere of reciprocal space, by a combination of 4 sets of ω scans; each set at different φ and/or 2θ angles and each scan (20 sec exposure) covering 0.3° in ω. Crystal to detector distance 4.42 cm. |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2366 (5) | 0.6253 (4) | 0.3429 (2) | 0.0158 (8) | |
O2 | 0.3986 (6) | 0.1485 (5) | 0.3613 (3) | 0.0220 (9) | |
H02 | 0.428 (10) | 0.141 (9) | 0.305 (5) | 0.05 (2)* | |
O3 | 0.2554 (5) | 0.6451 (4) | 0.1398 (2) | 0.0190 (9) | |
O4 | 0.3503 (5) | 0.3417 (4) | 0.1498 (3) | 0.0216 (9) | |
O5 | 0.0797 (5) | 0.8712 (4) | 0.6781 (2) | 0.0192 (9) | |
O6 | 0.1459 (5) | 0.6253 (4) | 0.7964 (3) | 0.0220 (9) | |
O7 | 0.1232 (5) | 1.0983 (4) | 0.8935 (3) | 0.0218 (9) | |
O8 | 0.3601 (5) | 0.9942 (4) | 0.7869 (3) | 0.0218 (9) | |
C2 | 0.2970 (7) | 0.4714 (6) | 0.2985 (4) | 0.0153 (12) | |
C3 | 0.3363 (7) | 0.3220 (6) | 0.3723 (4) | 0.0150 (11) | |
C4 | 0.3096 (7) | 0.2983 (7) | 0.5700 (4) | 0.0159 (12) | |
H4 | 0.3517 | 0.1725 | 0.5872 | 0.019* | |
C5 | 0.2575 (7) | 0.4064 (7) | 0.6440 (4) | 0.0194 (12) | |
H5 | 0.2638 | 0.3529 | 0.7134 | 0.023* | |
C6 | 0.1950 (7) | 0.5938 (6) | 0.6205 (4) | 0.0137 (11) | |
C7 | 0.1855 (7) | 0.6798 (7) | 0.5196 (4) | 0.0184 (12) | |
H7 | 0.1452 | 0.8062 | 0.5025 | 0.022* | |
C8 | 0.2386 (7) | 0.5692 (6) | 0.4457 (4) | 0.0147 (12) | |
C9 | 0.2982 (7) | 0.3806 (6) | 0.4690 (4) | 0.0160 (12) | |
C10 | 0.3058 (7) | 0.4778 (7) | 0.1903 (4) | 0.0182 (12) | |
C11 | 0.1409 (8) | 0.6935 (7) | 0.7080 (4) | 0.0191 (12) | |
C12 | 0.0154 (8) | 0.9703 (7) | 0.7599 (4) | 0.0191 (12) | |
H121 | −0.0730 | 0.8940 | 0.8097 | 0.025* | |
H122 | −0.0584 | 1.0851 | 0.7329 | 0.025* | |
C13 | 0.1879 (8) | 1.0177 (6) | 0.8122 (4) | 0.0185 (12) | |
C14 | 0.2700 (9) | 1.1704 (7) | 0.9467 (4) | 0.0322 (15) | |
H141 | 0.2086 | 1.2114 | 1.0086 | 0.070 (13)* | |
H142 | 0.3296 | 1.2751 | 0.9024 | 0.070 (13)* | |
H143 | 0.3709 | 1.0736 | 0.9650 | 0.070 (13)* | |
C15 | 0.2432 (8) | 0.6532 (7) | 0.0305 (4) | 0.0247 (14) | |
H151 | 0.1607 | 0.5558 | 0.0184 | 0.042 (10)* | |
H152 | 0.3745 | 0.6353 | −0.0020 | 0.042 (10)* | |
H153 | 0.1864 | 0.7739 | 0.0017 | 0.042 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.014 (2) | 0.0165 (18) | 0.018 (2) | 0.0036 (15) | −0.0010 (15) | −0.0054 (16) |
O2 | 0.028 (2) | 0.017 (2) | 0.022 (2) | 0.0113 (16) | −0.0005 (18) | −0.0095 (18) |
O3 | 0.023 (2) | 0.0206 (19) | 0.012 (2) | 0.0030 (15) | −0.0024 (15) | −0.0007 (16) |
O4 | 0.023 (2) | 0.0191 (19) | 0.023 (2) | 0.0043 (16) | −0.0002 (16) | −0.0070 (17) |
O5 | 0.029 (2) | 0.0151 (18) | 0.0142 (19) | 0.0048 (15) | −0.0046 (16) | −0.0049 (15) |
O6 | 0.028 (2) | 0.0192 (19) | 0.017 (2) | 0.0043 (16) | −0.0042 (17) | −0.0009 (17) |
O7 | 0.022 (2) | 0.0253 (19) | 0.020 (2) | 0.0069 (16) | −0.0033 (16) | −0.0131 (17) |
O8 | 0.018 (2) | 0.0179 (19) | 0.030 (2) | 0.0021 (16) | −0.0016 (17) | −0.0070 (17) |
C2 | 0.018 (3) | 0.012 (3) | 0.018 (3) | −0.001 (2) | 0.001 (2) | −0.011 (2) |
C3 | 0.014 (3) | 0.016 (3) | 0.016 (3) | −0.001 (2) | −0.002 (2) | −0.003 (2) |
C4 | 0.012 (3) | 0.016 (3) | 0.020 (3) | 0.006 (2) | −0.007 (2) | −0.001 (2) |
C5 | 0.016 (3) | 0.022 (3) | 0.020 (3) | −0.006 (2) | −0.001 (2) | −0.003 (2) |
C6 | 0.011 (3) | 0.014 (2) | 0.017 (3) | 0.003 (2) | −0.001 (2) | −0.007 (2) |
C7 | 0.018 (3) | 0.016 (3) | 0.023 (3) | −0.003 (2) | −0.003 (2) | −0.007 (2) |
C8 | 0.012 (3) | 0.016 (3) | 0.015 (3) | −0.001 (2) | −0.003 (2) | 0.000 (2) |
C9 | 0.010 (3) | 0.016 (3) | 0.025 (3) | 0.005 (2) | −0.004 (2) | −0.010 (2) |
C10 | 0.017 (3) | 0.016 (3) | 0.020 (3) | 0.005 (2) | −0.003 (2) | −0.002 (2) |
C11 | 0.019 (3) | 0.014 (3) | 0.025 (3) | −0.003 (2) | −0.002 (2) | −0.003 (2) |
C12 | 0.024 (3) | 0.017 (3) | 0.017 (3) | 0.008 (2) | 0.000 (2) | −0.009 (2) |
C13 | 0.025 (4) | 0.010 (2) | 0.019 (3) | 0.006 (2) | −0.001 (2) | −0.002 (2) |
C14 | 0.035 (4) | 0.028 (3) | 0.039 (4) | 0.002 (3) | −0.015 (3) | −0.018 (3) |
C15 | 0.027 (4) | 0.027 (3) | 0.019 (3) | 0.009 (2) | −0.003 (2) | −0.003 (3) |
O1—C8 | 1.367 (6) | O8—C13 | 1.212 (6) |
O1—C2 | 1.384 (5) | C2—C3 | 1.380 (6) |
O2—H02 | 0.77 (6) | C2—C10 | 1.431 (7) |
O2—C3 | 1.345 (6) | C3—C9 | 1.421 (7) |
O3—C10 | 1.342 (5) | C4—C5 | 1.374 (7) |
O3—C15 | 1.457 (6) | C4—C9 | 1.390 (7) |
O4—C10 | 1.221 (6) | C5—C6 | 1.409 (7) |
O5—C11 | 1.353 (6) | C6—C7 | 1.395 (6) |
O5—C12 | 1.432 (5) | C6—C11 | 1.485 (7) |
O6—C11 | 1.205 (6) | C7—C8 | 1.386 (7) |
O7—C13 | 1.348 (6) | C8—C9 | 1.411 (6) |
O7—C14 | 1.448 (6) | C12—C13 | 1.506 (7) |
C8—O1—C2 | 105.8 (3) | O1—C8—C7 | 125.2 (4) |
H02—O2—C3 | 111 (5) | O1—C8—C9 | 111.5 (4) |
C10—O3—C15 | 115.0 (4) | C7—C8—C9 | 123.2 (4) |
C11—O5—C12 | 114.6 (4) | C4—C9—C8 | 120.0 (4) |
C13—O7—C14 | 116.8 (4) | C4—C9—C3 | 135.6 (4) |
C3—C2—O1 | 110.4 (4) | C8—C9—C3 | 104.4 (4) |
C3—C2—C10 | 128.2 (4) | O4—C10—O3 | 124.4 (5) |
O1—C2—C10 | 121.3 (4) | O4—C10—C2 | 122.3 (4) |
O2—C3—C2 | 129.2 (4) | O3—C10—C2 | 113.2 (4) |
O2—C3—C9 | 123.1 (4) | O6—C11—O5 | 122.8 (5) |
C2—C3—C9 | 107.8 (4) | O6—C11—C6 | 124.7 (4) |
C5—C4—C9 | 117.4 (4) | O5—C11—C6 | 112.5 (4) |
C4—C5—C6 | 122.4 (5) | O5—C12—C13 | 110.5 (4) |
C7—C6—C5 | 121.1 (4) | O8—C13—O7 | 123.0 (5) |
C7—C6—C11 | 122.2 (4) | O8—C13—C12 | 127.6 (5) |
C5—C6—C11 | 116.7 (4) | O7—C13—C12 | 109.4 (4) |
C8—C7—C6 | 115.9 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H02···O8i | 0.77 (6) | 2.13 (6) | 2.768 (5) | 141 (6) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
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