Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989016011221/su5310sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2056989016011221/su5310Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989016011221/su5310Isup3.cml |
CCDC reference: 1491854
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.006 Å
- R factor = 0.055
- wR factor = 0.138
- Data-to-parameter ratio = 48.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00591 Ang. PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.294 Check
Alert level G PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed .. ! Info PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min) 2 Note PLAT931_ALERT_5_G Found Twin Law ( 0 0 1)[ ] Estimated BASF 0.40 Check PLAT996_ALERT_1_G Non-Standard SHELXL LIST 4 Style FCF Supplied .. ! Check
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).
C12H8O4 | Dx = 1.508 Mg m−3 |
Mr = 216.18 | Melting point: 469 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 3.8486 (8) Å | Cell parameters from 870 reflections |
b = 14.676 (2) Å | θ = 2.8–27.9° |
c = 16.866 (3) Å | µ = 0.12 mm−1 |
β = 92.12 (2)° | T = 299 K |
V = 952.0 (3) Å3 | Needle, colourless |
Z = 4 | 0.44 × 0.08 × 0.02 mm |
F(000) = 448 |
Oxford Diffraction Xcalibur with a Sapphire CCD detector diffractometer | 7096 independent reflections |
Radiation source: fine-focus sealed tube | 3811 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.08 |
Rotation method data acquisition using ω and phi scans. | θmax = 25.4°, θmin = 2.8° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)' | h = −4→4 |
Tmin = 0.951, Tmax = 0.998 | k = −17→17 |
7096 measured reflections | l = −20→20 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.138 | H-atom parameters constrained |
S = 0.86 | w = 1/[σ2(Fo2) + (0.0738P)2] where P = (Fo2 + 2Fc2)/3 |
7096 reflections | (Δ/σ)max = 0.002 |
147 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.7447 (9) | 0.00489 (18) | 0.37565 (18) | 0.0525 (10) | |
O2 | 0.3156 (8) | 0.26727 (18) | 0.50579 (14) | 0.0399 (9) | |
O3 | 0.7860 (9) | 0.28906 (17) | 0.24893 (16) | 0.0510 (10) | |
O4 | 0.1046 (9) | 0.3863 (2) | 0.56614 (18) | 0.0617 (11) | |
C1 | 0.6682 (13) | 0.0956 (3) | 0.3822 (3) | 0.0392 (13) | |
C2 | 0.8854 (13) | −0.0043 (3) | 0.3016 (3) | 0.0534 (15) | |
H2 | 0.9619 | −0.0595 | 0.2814 | 0.064* | |
C3 | 0.8989 (13) | 0.0740 (3) | 0.2626 (3) | 0.0477 (14) | |
H3 | 0.9832 | 0.0833 | 0.2123 | 0.057* | |
C4 | 0.7573 (13) | 0.1417 (3) | 0.3137 (2) | 0.0369 (12) | |
C5 | 0.6975 (12) | 0.2354 (3) | 0.3111 (2) | 0.0344 (12) | |
C6 | 0.5523 (11) | 0.2781 (3) | 0.3757 (2) | 0.0304 (11) | |
C7 | 0.4677 (11) | 0.2262 (3) | 0.4418 (2) | 0.0348 (12) | |
C8 | 0.5234 (12) | 0.1339 (3) | 0.4477 (3) | 0.0397 (13) | |
H8 | 0.4679 | 0.1003 | 0.4922 | 0.048* | |
C9 | 0.4692 (12) | 0.3738 (3) | 0.3771 (3) | 0.0373 (13) | |
H9 | 0.5221 | 0.4101 | 0.3339 | 0.045* | |
C10 | 0.3191 (12) | 0.4114 (3) | 0.4385 (2) | 0.0431 (13) | |
H10 | 0.2654 | 0.4732 | 0.4371 | 0.052* | |
C11 | 0.2370 (13) | 0.3592 (3) | 0.5074 (3) | 0.0433 (13) | |
C12 | 0.6549 (14) | 0.2653 (3) | 0.1726 (2) | 0.0652 (17) | |
H12A | 0.7936 | 0.2173 | 0.1516 | 0.098* | |
H12B | 0.6630 | 0.3175 | 0.1384 | 0.098* | |
H12C | 0.4187 | 0.2450 | 0.1758 | 0.098* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.075 (3) | 0.0265 (17) | 0.056 (2) | 0.0074 (19) | 0.006 (2) | −0.0024 (16) |
O2 | 0.054 (2) | 0.0343 (18) | 0.0321 (16) | 0.0034 (18) | 0.0073 (19) | 0.0003 (14) |
O3 | 0.081 (3) | 0.0419 (18) | 0.0300 (17) | −0.0206 (19) | 0.005 (2) | 0.0006 (15) |
O4 | 0.089 (3) | 0.052 (2) | 0.045 (2) | 0.018 (2) | 0.025 (2) | −0.0027 (18) |
C1 | 0.045 (4) | 0.029 (3) | 0.043 (3) | 0.000 (3) | −0.007 (3) | 0.000 (2) |
C2 | 0.063 (4) | 0.040 (3) | 0.058 (3) | 0.009 (3) | 0.010 (3) | −0.013 (3) |
C3 | 0.054 (4) | 0.041 (3) | 0.048 (3) | −0.001 (3) | 0.007 (3) | −0.006 (2) |
C4 | 0.040 (3) | 0.032 (3) | 0.039 (3) | −0.002 (3) | −0.001 (3) | −0.0073 (19) |
C5 | 0.036 (3) | 0.037 (3) | 0.030 (2) | −0.006 (3) | 0.001 (3) | 0.001 (2) |
C6 | 0.029 (3) | 0.029 (2) | 0.033 (2) | −0.002 (2) | −0.002 (2) | −0.001 (2) |
C7 | 0.041 (3) | 0.033 (3) | 0.031 (2) | −0.002 (3) | 0.005 (2) | −0.002 (2) |
C8 | 0.049 (4) | 0.033 (3) | 0.038 (3) | −0.002 (3) | 0.004 (3) | 0.008 (2) |
C9 | 0.047 (3) | 0.030 (3) | 0.035 (3) | −0.004 (2) | 0.002 (3) | 0.005 (2) |
C10 | 0.056 (4) | 0.029 (2) | 0.044 (3) | 0.004 (3) | 0.001 (3) | 0.003 (2) |
C11 | 0.046 (4) | 0.036 (3) | 0.048 (3) | 0.007 (3) | 0.006 (3) | −0.001 (2) |
C12 | 0.099 (5) | 0.060 (3) | 0.037 (3) | −0.013 (4) | 0.001 (3) | −0.003 (2) |
O1—C1 | 1.369 (5) | C4—C5 | 1.394 (6) |
O1—C2 | 1.386 (5) | C5—C6 | 1.391 (5) |
O2—C7 | 1.385 (4) | C6—C7 | 1.398 (5) |
O2—C11 | 1.383 (5) | C6—C9 | 1.442 (5) |
O3—C5 | 1.365 (4) | C7—C8 | 1.374 (5) |
O3—C12 | 1.409 (4) | C8—H8 | 0.9300 |
O4—C11 | 1.200 (5) | C9—C10 | 1.325 (5) |
C1—C8 | 1.376 (5) | C9—H9 | 0.9300 |
C1—C4 | 1.393 (6) | C10—C11 | 1.435 (5) |
C2—C3 | 1.327 (6) | C10—H10 | 0.9300 |
C2—H2 | 0.9300 | C12—H12A | 0.9600 |
C3—C4 | 1.435 (6) | C12—H12B | 0.9600 |
C3—H3 | 0.9300 | C12—H12C | 0.9600 |
C1—O1—C2 | 105.1 (3) | C8—C7—O2 | 116.2 (4) |
C7—O2—C11 | 122.6 (3) | C8—C7—C6 | 123.7 (4) |
C5—O3—C12 | 117.9 (3) | O2—C7—C6 | 120.1 (4) |
O1—C1—C8 | 123.8 (4) | C1—C8—C7 | 114.2 (4) |
O1—C1—C4 | 110.2 (4) | C1—C8—H8 | 122.9 |
C8—C1—C4 | 126.0 (4) | C7—C8—H8 | 122.9 |
C3—C2—O1 | 112.7 (4) | C10—C9—C6 | 121.4 (4) |
C3—C2—H2 | 123.7 | C10—C9—H9 | 119.3 |
O1—C2—H2 | 123.7 | C6—C9—H9 | 119.3 |
C2—C3—C4 | 106.2 (4) | C9—C10—C11 | 121.7 (4) |
C2—C3—H3 | 126.9 | C9—C10—H10 | 119.1 |
C4—C3—H3 | 126.9 | C11—C10—H10 | 119.1 |
C5—C4—C1 | 117.3 (4) | O4—C11—O2 | 116.1 (4) |
C5—C4—C3 | 136.9 (4) | O4—C11—C10 | 127.2 (4) |
C1—C4—C3 | 105.8 (4) | O2—C11—C10 | 116.8 (4) |
O3—C5—C6 | 117.4 (4) | O3—C12—H12A | 109.5 |
O3—C5—C4 | 123.2 (4) | O3—C12—H12B | 109.5 |
C6—C5—C4 | 119.4 (4) | H12A—C12—H12B | 109.5 |
C5—C6—C7 | 119.4 (4) | O3—C12—H12C | 109.5 |
C5—C6—C9 | 123.2 (4) | H12A—C12—H12C | 109.5 |
C7—C6—C9 | 117.4 (4) | H12B—C12—H12C | 109.5 |
C2—O1—C1—C8 | −179.8 (5) | C4—C5—C6—C9 | −177.6 (4) |
C2—O1—C1—C4 | 0.3 (5) | C11—O2—C7—C8 | −178.5 (4) |
C1—O1—C2—C3 | −0.2 (6) | C11—O2—C7—C6 | 0.9 (6) |
O1—C2—C3—C4 | 0.0 (6) | C5—C6—C7—C8 | 0.8 (6) |
O1—C1—C4—C5 | −179.6 (4) | C9—C6—C7—C8 | 178.3 (4) |
C8—C1—C4—C5 | 0.5 (7) | C5—C6—C7—O2 | −178.5 (4) |
O1—C1—C4—C3 | −0.3 (5) | C9—C6—C7—O2 | −1.1 (6) |
C8—C1—C4—C3 | 179.8 (5) | O1—C1—C8—C7 | −179.9 (5) |
C2—C3—C4—C5 | 179.2 (6) | C4—C1—C8—C7 | −0.1 (7) |
C2—C3—C4—C1 | 0.2 (6) | O2—C7—C8—C1 | 178.7 (4) |
C12—O3—C5—C6 | −126.8 (4) | C6—C7—C8—C1 | −0.6 (7) |
C12—O3—C5—C4 | 55.5 (6) | C5—C6—C9—C10 | 177.4 (5) |
C1—C4—C5—O3 | 177.3 (4) | C7—C6—C9—C10 | 0.1 (7) |
C3—C4—C5—O3 | −1.7 (9) | C6—C9—C10—C11 | 1.1 (7) |
C1—C4—C5—C6 | −0.3 (7) | C7—O2—C11—O4 | 179.7 (4) |
C3—C4—C5—C6 | −179.3 (5) | C7—O2—C11—C10 | 0.3 (6) |
O3—C5—C6—C7 | −178.0 (4) | C9—C10—C11—O4 | 179.3 (5) |
C4—C5—C6—C7 | −0.3 (6) | C9—C10—C11—O2 | −1.3 (7) |
O3—C5—C6—C9 | 4.7 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O3i | 0.93 | 2.49 | 3.406 (5) | 170 |
C3—H3···O4ii | 0.93 | 2.57 | 3.484 (6) | 170 |
C10—H10···O4iii | 0.93 | 2.51 | 3.387 (5) | 158 |
C12—H12A···O4ii | 0.96 | 2.44 | 3.376 (5) | 165 |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x+1, −y+1/2, z−1/2; (iii) −x, −y+1, −z+1. |