Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016236/wn2118sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016236/wn2118Isup2.hkl |
CCDC reference: 647461
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.004 Å
- R factor = 0.064
- wR factor = 0.149
- Data-to-parameter ratio = 10.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.17 Ratio PLAT391_ALERT_3_B Deviating Methyl C8 H-C-H Bond Angle ...... 99.00 Deg.
Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.18 Ratio PLAT355_ALERT_3_C Long O-H Bond (0.82A) O2B - H2Y ... 1.02 Ang. PLAT355_ALERT_3_C Long O-H Bond (0.82A) O4B - H4Y ... 1.06 Ang. PLAT390_ALERT_3_C Deviating Methyl C10 X-C-H Bond Angle ...... 102.00 Deg. PLAT708_ALERT_1_C D-H..A Calc 154(4), Rep 146(4), Dev.. 2.00 Sigma O2B -H2Y -O1B 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 6 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: COLLECT (Hooft, 1998); cell refinement: SCALEPACK (Otwinowski & Minor 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C10H10O4 | F(000) = 816 |
Mr = 194.18 | Dx = 1.446 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 18514 reflections |
a = 6.9666 (3) Å | θ = 3.4–26.0° |
b = 10.6786 (7) Å | µ = 0.11 mm−1 |
c = 24.0792 (14) Å | T = 173 K |
β = 95.215 (4)° | Needle, colourless |
V = 1783.92 (17) Å3 | 0.1 × 0.05 × 0.02 mm |
Z = 8 |
Nonius KappaCCD area-detector diffractometer | 2097 reflections with I > 2σ(I) |
Radiation source: Enraf–Nonius FR590 | Rint = 0.082 |
Graphite monochromator | θmax = 26.0°, θmin = 3.5° |
Detector resolution: 9 pixels mm-1 | h = −8→8 |
φ and ω scans | k = −13→10 |
9562 measured reflections | l = −29→29 |
3482 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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | All H-atom parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0505P)2 + 0.8082P] where P = (Fo2 + 2Fc2)/3 |
3482 reflections | (Δ/σ)max < 0.001 |
333 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Experimental. IR (KBr, v, cm-1): 3252 (br, O—H), 1630, 1640, 1507, 1447, 1372, 1322, 1275. 1H-NMR (400 MHz, DMSO– d6, 298 K, TMS): δ 2.2 (3H, s, CH3), 2.8 (3H, s, CH3), 6.4 (1H, d, aromatic), 8.5 (1H, d, aromatic), 12.7 (1H, s, OH), 12.9 (1H, s, OH). |
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 | ||
O1 | 0.1763 (3) | 0.6426 (2) | 0.05237 (8) | 0.0343 (5) | |
H1X | 0.177 (5) | 0.714 (4) | 0.0343 (15) | 0.082 (13)* | |
O2 | 0.1363 (3) | 0.35739 (19) | 0.16600 (8) | 0.0423 (6) | |
O3 | 0.1054 (3) | 0.5180 (2) | 0.23973 (8) | 0.0402 (6) | |
H3X | 0.125 (6) | 0.440 (4) | 0.2193 (18) | 0.106 (16)* | |
O4 | 0.1694 (3) | 0.87242 (19) | 0.03130 (8) | 0.0426 (6) | |
C1 | 0.1229 (3) | 0.7964 (3) | 0.12072 (10) | 0.0287 (7) | |
C2 | 0.1431 (3) | 0.6702 (3) | 0.10482 (10) | 0.0264 (7) | |
C3 | 0.1304 (3) | 0.5714 (3) | 0.14358 (10) | 0.0267 (6) | |
C4 | 0.1069 (3) | 0.6048 (3) | 0.19934 (11) | 0.0316 (7) | |
C5 | 0.0835 (4) | 0.7297 (3) | 0.21518 (12) | 0.0346 (7) | |
H5 | 0.057 (3) | 0.747 (3) | 0.2539 (11) | 0.040 (8)* | |
C6 | 0.0909 (4) | 0.8223 (3) | 0.17652 (12) | 0.0328 (7) | |
H6 | 0.080 (4) | 0.905 (3) | 0.1855 (11) | 0.036 (8)* | |
C7 | 0.1351 (4) | 0.8967 (3) | 0.08014 (12) | 0.0345 (7) | |
C8 | 0.1052 (6) | 1.0311 (3) | 0.09562 (17) | 0.0505 (9) | |
H8C | 0.104 (6) | 1.078 (5) | 0.061 (2) | 0.121 (17)* | |
H8B | 0.205 (7) | 1.062 (5) | 0.126 (2) | 0.15 (2)* | |
H8A | −0.010 (7) | 1.038 (4) | 0.116 (2) | 0.119 (17)* | |
C9 | 0.1384 (4) | 0.4386 (3) | 0.12870 (11) | 0.0322 (7) | |
C10 | 0.1418 (5) | 0.3937 (3) | 0.07027 (13) | 0.0402 (8) | |
H10C | 0.128 (5) | 0.303 (4) | 0.0744 (14) | 0.076 (12)* | |
H10B | 0.265 (4) | 0.416 (3) | 0.0552 (12) | 0.051 (9)* | |
H10A | 0.041 (4) | 0.430 (3) | 0.0458 (12) | 0.050 (9)* | |
O1B | 0.3368 (3) | −0.16272 (19) | 0.44189 (8) | 0.0416 (6) | |
O2B | 0.3394 (3) | 0.0705 (2) | 0.45077 (8) | 0.0371 (5) | |
H2Y | 0.332 (6) | −0.023 (4) | 0.4582 (17) | 0.105 (15)* | |
O3B | 0.3839 (3) | 0.4167 (2) | 0.37683 (9) | 0.0460 (6) | |
O4B | 0.4039 (3) | 0.3096 (2) | 0.28639 (9) | 0.0428 (6) | |
H4Y | 0.394 (5) | 0.380 (4) | 0.3170 (18) | 0.101 (14)* | |
C1B | 0.3701 (3) | −0.0332 (3) | 0.36456 (11) | 0.0277 (6) | |
C2B | 0.3600 (3) | 0.0783 (3) | 0.39647 (10) | 0.0269 (6) | |
C3B | 0.3735 (3) | 0.1978 (3) | 0.37175 (10) | 0.0271 (6) | |
C4B | 0.3922 (4) | 0.2006 (3) | 0.31344 (11) | 0.0318 (7) | |
C5B | 0.3995 (4) | 0.0921 (3) | 0.28191 (12) | 0.0362 (7) | |
H5B | 0.414 (3) | 0.098 (3) | 0.2437 (11) | 0.033 (7)* | |
C6B | 0.3900 (4) | −0.0220 (3) | 0.30713 (12) | 0.0335 (7) | |
H6B | 0.397 (4) | −0.097 (3) | 0.2856 (11) | 0.034 (8)* | |
C7B | 0.3627 (4) | −0.1548 (3) | 0.39150 (12) | 0.0315 (7) | |
C8B | 0.3894 (6) | −0.2733 (3) | 0.36007 (16) | 0.0475 (9) | |
H8F | 0.289 (5) | −0.286 (4) | 0.3299 (17) | 0.096 (14)* | |
H8E | 0.510 (5) | −0.270 (3) | 0.3405 (14) | 0.072 (11)* | |
H8D | 0.402 (5) | −0.347 (4) | 0.3881 (16) | 0.091 (13)* | |
C9B | 0.3668 (4) | 0.3161 (3) | 0.40242 (12) | 0.0343 (7) | |
C10B | 0.3426 (5) | 0.3249 (3) | 0.46319 (13) | 0.0390 (8) | |
H10F | 0.226 (4) | 0.281 (3) | 0.4713 (11) | 0.049 (9)* | |
H10E | 0.451 (4) | 0.283 (3) | 0.4866 (12) | 0.054 (9)* | |
H10D | 0.339 (5) | 0.416 (4) | 0.4726 (14) | 0.072 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0429 (12) | 0.0347 (13) | 0.0260 (11) | 0.0006 (10) | 0.0079 (8) | 0.0008 (10) |
O2 | 0.0541 (13) | 0.0339 (13) | 0.0401 (13) | 0.0006 (11) | 0.0103 (9) | 0.0066 (11) |
O3 | 0.0477 (12) | 0.0462 (15) | 0.0278 (11) | 0.0045 (11) | 0.0091 (9) | 0.0082 (10) |
O4 | 0.0530 (13) | 0.0379 (13) | 0.0382 (13) | 0.0010 (11) | 0.0112 (10) | 0.0074 (10) |
C1 | 0.0236 (14) | 0.0309 (18) | 0.0319 (16) | −0.0023 (13) | 0.0037 (11) | 0.0011 (13) |
C2 | 0.0193 (13) | 0.0355 (19) | 0.0248 (15) | −0.0011 (12) | 0.0032 (10) | −0.0003 (13) |
C3 | 0.0224 (13) | 0.0325 (18) | 0.0256 (15) | 0.0010 (12) | 0.0042 (10) | 0.0015 (13) |
C4 | 0.0236 (14) | 0.0419 (19) | 0.0297 (16) | 0.0006 (13) | 0.0044 (11) | 0.0057 (14) |
C5 | 0.0309 (15) | 0.047 (2) | 0.0263 (15) | 0.0026 (14) | 0.0034 (11) | −0.0056 (15) |
C6 | 0.0286 (15) | 0.033 (2) | 0.0369 (17) | 0.0011 (14) | 0.0023 (12) | −0.0050 (15) |
C7 | 0.0288 (15) | 0.0350 (19) | 0.0397 (18) | −0.0012 (13) | 0.0042 (12) | 0.0028 (15) |
C8 | 0.072 (3) | 0.028 (2) | 0.053 (2) | 0.0016 (18) | 0.014 (2) | 0.0009 (17) |
C9 | 0.0250 (14) | 0.0380 (19) | 0.0338 (16) | 0.0029 (13) | 0.0043 (11) | 0.0044 (14) |
C10 | 0.054 (2) | 0.033 (2) | 0.0341 (18) | 0.0025 (17) | 0.0074 (15) | 0.0004 (15) |
O1B | 0.0519 (13) | 0.0350 (13) | 0.0389 (12) | −0.0015 (10) | 0.0099 (9) | 0.0066 (10) |
O2B | 0.0493 (12) | 0.0343 (13) | 0.0291 (11) | 0.0003 (10) | 0.0117 (9) | 0.0009 (9) |
O3B | 0.0567 (14) | 0.0315 (13) | 0.0507 (14) | 0.0002 (11) | 0.0092 (10) | 0.0051 (11) |
O4B | 0.0455 (13) | 0.0424 (14) | 0.0416 (13) | 0.0003 (11) | 0.0099 (9) | 0.0153 (11) |
C1B | 0.0233 (14) | 0.0291 (17) | 0.0312 (15) | 0.0007 (13) | 0.0044 (11) | 0.0004 (13) |
C2B | 0.0217 (13) | 0.0358 (19) | 0.0237 (14) | 0.0030 (13) | 0.0049 (10) | 0.0033 (13) |
C3B | 0.0231 (14) | 0.0291 (17) | 0.0295 (15) | 0.0012 (12) | 0.0048 (10) | 0.0021 (13) |
C4B | 0.0261 (14) | 0.0359 (18) | 0.0334 (16) | 0.0003 (13) | 0.0029 (11) | 0.0089 (14) |
C5B | 0.0377 (17) | 0.044 (2) | 0.0273 (16) | 0.0015 (15) | 0.0079 (12) | 0.0042 (16) |
C6B | 0.0293 (15) | 0.040 (2) | 0.0315 (17) | 0.0015 (14) | 0.0062 (12) | −0.0049 (15) |
C7B | 0.0263 (14) | 0.0336 (19) | 0.0344 (17) | −0.0011 (13) | 0.0019 (12) | 0.0007 (14) |
C8B | 0.059 (2) | 0.032 (2) | 0.050 (2) | 0.0050 (18) | 0.0013 (18) | −0.0041 (17) |
C9B | 0.0264 (15) | 0.034 (2) | 0.0435 (18) | 0.0002 (13) | 0.0069 (12) | 0.0051 (15) |
C10B | 0.0427 (19) | 0.035 (2) | 0.0391 (18) | 0.0002 (17) | 0.0037 (14) | −0.0032 (15) |
O1—C2 | 1.337 (3) | O1B—C7B | 1.246 (3) |
O1—H1X | 0.88 (4) | O2B—C2B | 1.331 (3) |
O2—C9 | 1.250 (3) | O2B—H2Y | 1.01 (5) |
O3—C4 | 1.345 (3) | O3B—C9B | 1.249 (3) |
O3—H3X | 0.98 (4) | O4B—C4B | 1.339 (3) |
O4—C7 | 1.249 (3) | O4B—H4Y | 1.06 (4) |
C1—C6 | 1.409 (4) | C1B—C6B | 1.407 (4) |
C1—C2 | 1.412 (4) | C1B—C2B | 1.422 (4) |
C1—C7 | 1.458 (4) | C1B—C7B | 1.456 (4) |
C2—C3 | 1.417 (4) | C2B—C3B | 1.415 (4) |
C3—C4 | 1.413 (4) | C3B—C4B | 1.422 (3) |
C3—C9 | 1.464 (4) | C3B—C9B | 1.466 (4) |
C4—C5 | 1.400 (4) | C4B—C5B | 1.389 (4) |
C5—C6 | 1.362 (4) | C5B—C6B | 1.366 (4) |
C5—H5 | 0.98 (3) | C5B—H5B | 0.94 (3) |
C6—H6 | 0.92 (3) | C6B—H6B | 0.96 (3) |
C7—C8 | 1.502 (4) | C7B—C8B | 1.494 (4) |
C8—H8C | 0.98 (5) | C8B—H8F | 0.97 (4) |
C8—H8B | 1.03 (5) | C8B—H8E | 1.00 (3) |
C8—H8A | 0.99 (5) | C8B—H8D | 1.03 (4) |
C9—C10 | 1.489 (4) | C9B—C10B | 1.491 (4) |
C10—H10C | 0.98 (4) | C10B—H10F | 0.97 (3) |
C10—H10B | 0.99 (3) | C10B—H10E | 1.01 (3) |
C10—H10A | 0.96 (3) | C10B—H10D | 1.00 (4) |
C2—O1—H1X | 107 (2) | C2B—O2B—H2Y | 104 (2) |
C4—O3—H3X | 102 (2) | C4B—O4B—H4Y | 105 (2) |
C6—C1—C2 | 118.3 (3) | C6B—C1B—C2B | 118.3 (3) |
C6—C1—C7 | 121.2 (3) | C6B—C1B—C7B | 121.6 (3) |
C2—C1—C7 | 120.5 (2) | C2B—C1B—C7B | 120.1 (2) |
O1—C2—C1 | 119.8 (2) | O2B—C2B—C3B | 119.2 (2) |
O1—C2—C3 | 119.0 (2) | O2B—C2B—C1B | 119.5 (2) |
C1—C2—C3 | 121.2 (2) | C3B—C2B—C1B | 121.3 (2) |
C4—C3—C2 | 117.2 (3) | C2B—C3B—C4B | 116.7 (2) |
C4—C3—C9 | 119.2 (2) | C2B—C3B—C9B | 124.0 (2) |
C2—C3—C9 | 123.6 (2) | C4B—C3B—C9B | 119.3 (3) |
O3—C4—C5 | 116.8 (3) | O4B—C4B—C5B | 116.9 (2) |
O3—C4—C3 | 121.5 (3) | O4B—C4B—C3B | 120.9 (3) |
C5—C4—C3 | 121.7 (3) | C5B—C4B—C3B | 122.2 (3) |
C6—C5—C4 | 119.5 (3) | C6B—C5B—C4B | 119.7 (3) |
C6—C5—H5 | 122.5 (17) | C6B—C5B—H5B | 120.8 (17) |
C4—C5—H5 | 118.0 (17) | C4B—C5B—H5B | 119.5 (17) |
C5—C6—C1 | 121.9 (3) | C5B—C6B—C1B | 121.7 (3) |
C5—C6—H6 | 122.2 (17) | C5B—C6B—H6B | 120.1 (16) |
C1—C6—H6 | 115.9 (17) | C1B—C6B—H6B | 118.2 (17) |
O4—C7—C1 | 120.4 (3) | O1B—C7B—C1B | 120.6 (3) |
O4—C7—C8 | 118.4 (3) | O1B—C7B—C8B | 118.2 (3) |
C1—C7—C8 | 121.2 (3) | C1B—C7B—C8B | 121.2 (3) |
C7—C8—H8C | 105 (3) | C7B—C8B—H8F | 113 (2) |
C7—C8—H8B | 113 (3) | C7B—C8B—H8E | 111 (2) |
H8C—C8—H8B | 114 (4) | H8F—C8B—H8E | 103 (3) |
C7—C8—H8A | 110 (3) | C7B—C8B—H8D | 109 (2) |
H8C—C8—H8A | 117 (4) | H8F—C8B—H8D | 113 (3) |
H8B—C8—H8A | 98 (4) | H8E—C8B—H8D | 108 (3) |
O2—C9—C3 | 119.5 (2) | O3B—C9B—C3B | 118.9 (2) |
O2—C9—C10 | 117.2 (3) | O3B—C9B—C10B | 117.0 (3) |
C3—C9—C10 | 123.2 (3) | C3B—C9B—C10B | 124.0 (3) |
C9—C10—H10C | 102 (2) | C9B—C10B—H10F | 109.7 (17) |
C9—C10—H10B | 111.0 (17) | C9B—C10B—H10E | 112.1 (17) |
H10C—C10—H10B | 112 (3) | H10F—C10B—H10E | 106 (2) |
C9—C10—H10A | 112.1 (18) | C9B—C10B—H10D | 107 (2) |
H10C—C10—H10A | 113 (3) | H10F—C10B—H10D | 113 (3) |
H10B—C10—H10A | 107 (2) | H10E—C10B—H10D | 110 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1X···O4 | 0.88 (4) | 1.69 (4) | 2.506 (3) | 153 (4) |
O2B—H2Y···O1B | 1.01 (4) | 1.55 (4) | 2.499 (3) | 146 (4) |
O3—H3X···O2 | 0.98 (4) | 1.57 (4) | 2.492 (3) | 155 (4) |
O4B—H4Y···O3B | 1.06 (4) | 1.50 (4) | 2.475 (3) | 150 (4) |
C6B—H6B···O4Bi | 0.96 (3) | 2.52 (3) | 3.310 (4) | 140 (2) |
C8B—H8D···O3Bii | 1.04 (4) | 2.54 (4) | 3.336 (4) | 133 (3) |
C10B—H10E···O1Biii | 1.01 (3) | 2.52 (3) | 3.505 (4) | 167 (2) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) −x+1, −y, −z+1. |
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