Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804007755/fl6091sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804007755/fl6091Isup2.hkl |
CCDC reference: 239136
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.134
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C9 .. 5.12 su PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C2 ... 1.53 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis RED (Oxford Diffraction, 2001); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON2002 (Spek, 2002); software used to prepare material for publication: SHELXL97.
C11H12O4 | F(000) = 220 |
Mr = 208.21 | Dx = 1.333 Mg m−3 |
Triclinic, P1 | Melting point: not measured K |
a = 7.927 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.185 (2) Å | Cell parameters from 1238 reflections |
c = 10.018 (2) Å | θ = 2.3–22.1° |
α = 65.00 (2)° | µ = 0.10 mm−1 |
β = 72.01 (2)° | T = 298 K |
γ = 62.82 (2)° | Prism, yellow |
V = 518.6 (2) Å3 | 0.52 × 0.34 × 0.06 mm |
Z = 2 |
Oxford Diffraction Xcalibur CCD diffractometer | 1102 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 26.4°, θmin = 4.3° |
Detector resolution: Sapphire CCD detector pixels mm-1 | h = −9→9 |
Rotation method data acquisition using ω scans | k = −10→10 |
4883 measured reflections | l = −12→12 |
2054 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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 0.84 | w = 1/[σ2(Fo2) + (0.0801P)2] where P = (Fo2 + 2Fc2)/3 |
2054 reflections | (Δ/σ)max = 0.010 |
136 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
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 | ||
C1 | 0.3648 (3) | 1.1266 (3) | 0.3107 (2) | 0.0471 (5) | |
C2 | 0.3313 (3) | 1.3399 (3) | 0.2203 (2) | 0.0521 (6) | |
C3 | 0.2852 (4) | 1.4119 (4) | 0.0689 (3) | 0.0784 (8) | |
H3A | 0.1695 | 1.3976 | 0.0742 | 0.094* | |
H3B | 0.3883 | 1.3381 | 0.0110 | 0.094* | |
H3C | 0.2679 | 1.5468 | 0.0230 | 0.094* | |
C4 | 0.2565 (3) | 1.0729 (3) | 0.4595 (2) | 0.0407 (5) | |
C5 | 0.1324 (3) | 1.2075 (3) | 0.5290 (2) | 0.0480 (5) | |
H5 | 0.1214 | 1.3366 | 0.4838 | 0.058* | |
C6 | 0.0245 (3) | 1.1526 (3) | 0.6649 (2) | 0.0511 (6) | |
H6 | −0.0574 | 1.2442 | 0.7115 | 0.061* | |
C7 | 0.0378 (3) | 0.9625 (3) | 0.7319 (2) | 0.0451 (5) | |
C8 | 0.1632 (3) | 0.8237 (3) | 0.6619 (2) | 0.0430 (5) | |
C9 | 0.2711 (3) | 0.8791 (3) | 0.5290 (2) | 0.0436 (5) | |
H9 | 0.3557 | 0.7870 | 0.4835 | 0.052* | |
C10 | −0.2136 (3) | 1.0335 (4) | 0.9293 (3) | 0.0739 (7) | |
H10A | −0.3062 | 1.1232 | 0.8626 | 0.089* | |
H10B | −0.1593 | 1.1035 | 0.9487 | 0.089* | |
H10C | −0.2749 | 0.9668 | 1.0211 | 0.089* | |
C11 | 0.2866 (3) | 0.4928 (3) | 0.6726 (2) | 0.0634 (7) | |
H11A | 0.4166 | 0.4771 | 0.6649 | 0.076* | |
H11B | 0.2576 | 0.5293 | 0.5753 | 0.076* | |
H11C | 0.2708 | 0.3723 | 0.7347 | 0.076* | |
O1 | 0.4823 (2) | 1.0083 (2) | 0.25114 (16) | 0.0686 (5) | |
O2 | 0.3489 (2) | 1.4407 (2) | 0.27208 (18) | 0.0746 (5) | |
O3 | −0.0651 (2) | 0.8949 (2) | 0.86332 (15) | 0.0626 (5) | |
O4 | 0.1604 (2) | 0.64078 (19) | 0.73622 (15) | 0.0582 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0436 (12) | 0.0465 (11) | 0.0476 (12) | −0.0126 (10) | −0.0060 (10) | −0.0178 (10) |
C2 | 0.0449 (13) | 0.0513 (13) | 0.0521 (13) | −0.0186 (10) | −0.0008 (10) | −0.0139 (11) |
C3 | 0.098 (2) | 0.0688 (16) | 0.0591 (15) | −0.0383 (15) | −0.0159 (14) | −0.0019 (13) |
C4 | 0.0409 (11) | 0.0358 (10) | 0.0444 (11) | −0.0108 (9) | −0.0102 (9) | −0.0139 (9) |
C5 | 0.0496 (13) | 0.0384 (10) | 0.0548 (13) | −0.0144 (10) | −0.0056 (10) | −0.0183 (10) |
C6 | 0.0519 (13) | 0.0438 (11) | 0.0565 (13) | −0.0111 (10) | 0.0001 (11) | −0.0289 (11) |
C7 | 0.0443 (12) | 0.0472 (12) | 0.0405 (11) | −0.0137 (9) | −0.0049 (9) | −0.0165 (10) |
C8 | 0.0471 (12) | 0.0357 (10) | 0.0417 (11) | −0.0111 (9) | −0.0089 (9) | −0.0120 (9) |
C9 | 0.0422 (12) | 0.0395 (10) | 0.0444 (12) | −0.0057 (9) | −0.0067 (9) | −0.0200 (9) |
C10 | 0.0673 (16) | 0.0789 (16) | 0.0644 (15) | −0.0232 (13) | 0.0176 (13) | −0.0378 (14) |
C11 | 0.0787 (16) | 0.0373 (11) | 0.0654 (15) | −0.0163 (11) | −0.0081 (13) | −0.0171 (11) |
O1 | 0.0708 (11) | 0.0564 (9) | 0.0574 (10) | −0.0141 (8) | 0.0084 (8) | −0.0235 (8) |
O2 | 0.0878 (13) | 0.0578 (10) | 0.0826 (12) | −0.0322 (9) | −0.0140 (9) | −0.0208 (9) |
O3 | 0.0659 (10) | 0.0565 (9) | 0.0525 (9) | −0.0211 (8) | 0.0113 (8) | −0.0227 (8) |
O4 | 0.0716 (11) | 0.0393 (8) | 0.0507 (9) | −0.0173 (7) | 0.0013 (7) | −0.0144 (7) |
C1—O1 | 1.218 (2) | C7—O3 | 1.356 (2) |
C1—C4 | 1.467 (3) | C7—C8 | 1.408 (3) |
C1—C2 | 1.526 (3) | C8—C9 | 1.360 (3) |
C2—O2 | 1.217 (2) | C8—O4 | 1.369 (2) |
C2—C3 | 1.473 (3) | C9—H9 | 0.9300 |
C3—H3A | 0.9600 | C10—O3 | 1.429 (2) |
C3—H3B | 0.9600 | C10—H10A | 0.9600 |
C3—H3C | 0.9600 | C10—H10B | 0.9600 |
C4—C5 | 1.380 (2) | C10—H10C | 0.9600 |
C4—C9 | 1.401 (3) | C11—O4 | 1.423 (2) |
C5—C6 | 1.379 (3) | C11—H11A | 0.9600 |
C5—H5 | 0.9300 | C11—H11B | 0.9600 |
C6—C7 | 1.376 (3) | C11—H11C | 0.9600 |
C6—H6 | 0.9300 | ||
O1—C1—C4 | 123.4 (2) | O3—C7—C8 | 115.4 (2) |
O1—C1—C2 | 116.1 (2) | C6—C7—C8 | 119.80 (18) |
C4—C1—C2 | 120.5 (2) | C9—C8—O4 | 125.8 (2) |
O2—C2—C3 | 122.9 (2) | C9—C8—C7 | 119.45 (18) |
O2—C2—C1 | 120.1 (2) | O4—C8—C7 | 114.8 (2) |
C3—C2—C1 | 117.0 (2) | C8—C9—C4 | 121.0 (2) |
C2—C3—H3A | 109.5 | C8—C9—H9 | 119.5 |
C2—C3—H3B | 109.5 | C4—C9—H9 | 119.5 |
H3A—C3—H3B | 109.5 | O3—C10—H10A | 109.5 |
C2—C3—H3C | 109.5 | O3—C10—H10B | 109.5 |
H3A—C3—H3C | 109.5 | H10A—C10—H10B | 109.5 |
H3B—C3—H3C | 109.5 | O3—C10—H10C | 109.5 |
C5—C4—C9 | 118.95 (18) | H10A—C10—H10C | 109.5 |
C5—C4—C1 | 122.61 (17) | H10B—C10—H10C | 109.5 |
C9—C4—C1 | 118.31 (16) | O4—C11—H11A | 109.5 |
C6—C5—C4 | 120.65 (18) | O4—C11—H11B | 109.5 |
C6—C5—H5 | 119.7 | H11A—C11—H11B | 109.5 |
C4—C5—H5 | 119.7 | O4—C11—H11C | 109.5 |
C7—C6—C5 | 120.17 (18) | H11A—C11—H11C | 109.5 |
C7—C6—H6 | 119.9 | H11B—C11—H11C | 109.5 |
C5—C6—H6 | 119.9 | C7—O3—C10 | 118.0 (2) |
O3—C7—C6 | 124.7 (2) | C8—O4—C11 | 117.5 (2) |
O1—C1—C2—O2 | −125.0 (2) | O3—C7—C8—C9 | 179.5 (2) |
C4—C1—C2—O2 | 56.1 (3) | C6—C7—C8—C9 | 0.5 (3) |
O1—C1—C2—C3 | 52.8 (3) | O3—C7—C8—O4 | 0.9 (3) |
C4—C1—C2—C3 | −126.2 (2) | C6—C7—C8—O4 | −178.1 (2) |
O1—C1—C4—C5 | 176.0 (2) | O4—C8—C9—C4 | 177.18 (18) |
C2—C1—C4—C5 | −5.1 (3) | C7—C8—C9—C4 | −1.2 (3) |
O1—C1—C4—C9 | −8.2 (3) | C5—C4—C9—C8 | 0.9 (3) |
C2—C1—C4—C9 | 170.68 (19) | C1—C4—C9—C8 | −175.04 (18) |
C9—C4—C5—C6 | 0.2 (3) | C6—C7—O3—C10 | 7.5 (3) |
C1—C4—C5—C6 | 175.92 (19) | C8—C7—O3—C10 | −171.4 (2) |
C4—C5—C6—C7 | −0.9 (3) | C9—C8—O4—C11 | 2.7 (3) |
C5—C6—C7—O3 | −178.38 (19) | C7—C8—O4—C11 | −178.84 (17) |
C5—C6—C7—C8 | 0.6 (3) |
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