Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026195/bt2133sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026195/bt2133Isup2.hkl |
CCDC reference: 618134
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.110
- Data-to-parameter ratio = 9.9
checkCIF/PLATON results
No syntax errors found
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.08 From the CIF: _reflns_number_total 1194 Count of symmetry unique reflns 1196 Completeness (_total/calc) 99.83% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C10H10O3 | F(000) = 376 |
Mr = 178.18 | Dx = 1.419 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2015 reflections |
a = 15.193 (4) Å | θ = 2.7–23.8° |
b = 7.280 (2) Å | µ = 0.11 mm−1 |
c = 7.538 (2) Å | T = 120 K |
V = 833.8 (4) Å3 | Block, colorless |
Z = 4 | 0.45 × 0.31 × 0.25 mm |
Bruker SMART CCD area-detector diffractometer | 1194 independent reflections |
Radiation source: sealed tube | 1073 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
φ and ω scans | θmax = 28.1°, θmin = 2.7° |
Absorption correction: multi-scan SADABS (Bruker, 2002) | h = −20→16 |
Tmin = 0.954, Tmax = 0.978 | k = −9→9 |
7657 measured reflections | l = −9→9 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.058P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.25 | (Δ/σ)max < 0.001 |
1194 reflections | Δρmax = 0.24 e Å−3 |
120 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.009 (2) |
Experimental. [αD] = -67.7 (c 0.0027, MeOH, 295 K); IR (film) νmax 3694, 3063, 2991, 1672, 1548, 1429, 1248, 989, 896 cm-1; 1H NMR (500 MHz, CDCl3): δ 7.43 (1H, dd, J = 8.4 Hz, H-6), 6.92 (d, 1H, J = 8.4 Hz, H-5), 6.71 (d, 1H, J = 8.4 Hz, H-7), 4.67 (1H, m, H-3), 2.95 (d, 2H, J = 7.6 Hz, H-4), 1.55 (d, 3H, J = 6.3 Hz, Me); 13C NMR (125 MHz, CDCl3): δ 169.9 (C-1), 162.2 (C-8), 139.3 (C-4a), 136.1 (C-6), 117.8 (C-5), 116.2 (C-7), 108.3 (C-8a), 76.0 (C-3), 34.6 (C-4), 20.7 (Me). EIMS m/z 178 (100) [M+], 171 (76), 134 (93), 106 (32), 78 (30), 57 (16). |
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 | 0.59670 (10) | 0.3867 (2) | 0.5521 (2) | 0.0286 (4) | |
O2 | 0.64402 (11) | 0.1173 (2) | 0.4759 (3) | 0.0373 (5) | |
O3 | 0.80606 (12) | 0.0253 (2) | 0.5186 (3) | 0.0408 (5) | |
H3 | 0.7534 | 0.0104 | 0.4875 | 0.061* | |
C1 | 0.66184 (15) | 0.2692 (3) | 0.5286 (3) | 0.0278 (5) | |
C2 | 0.75146 (15) | 0.3290 (3) | 0.5633 (3) | 0.0251 (5) | |
C3 | 0.81965 (16) | 0.2022 (3) | 0.5582 (3) | 0.0294 (5) | |
C4 | 0.90491 (17) | 0.2584 (4) | 0.5922 (3) | 0.0323 (6) | |
H4A | 0.9516 | 0.1715 | 0.5929 | 0.039* | |
C5 | 0.92154 (16) | 0.4386 (4) | 0.6245 (3) | 0.0313 (6) | |
H5A | 0.9802 | 0.4762 | 0.6481 | 0.038* | |
C6 | 0.85571 (15) | 0.5676 (3) | 0.6240 (3) | 0.0274 (5) | |
H6A | 0.8691 | 0.6932 | 0.6447 | 0.033* | |
C7 | 0.77026 (15) | 0.5142 (3) | 0.5934 (3) | 0.0240 (5) | |
C8 | 0.69540 (15) | 0.6451 (3) | 0.5845 (3) | 0.0262 (5) | |
H8A | 0.6872 | 0.6866 | 0.4606 | 0.031* | |
H8B | 0.7086 | 0.7541 | 0.6583 | 0.031* | |
C9 | 0.61245 (15) | 0.5558 (3) | 0.6493 (3) | 0.0282 (5) | |
H9A | 0.6188 | 0.5267 | 0.7784 | 0.034* | |
C10 | 0.53189 (16) | 0.6707 (4) | 0.6228 (4) | 0.0377 (6) | |
H10A | 0.4804 | 0.6049 | 0.6685 | 0.057* | |
H10B | 0.5239 | 0.6952 | 0.4960 | 0.057* | |
H10C | 0.5386 | 0.7872 | 0.6865 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0226 (8) | 0.0297 (8) | 0.0335 (9) | −0.0001 (7) | 0.0001 (7) | 0.0005 (7) |
O2 | 0.0354 (10) | 0.0260 (8) | 0.0506 (11) | −0.0043 (8) | −0.0027 (8) | −0.0027 (8) |
O3 | 0.0358 (10) | 0.0254 (9) | 0.0612 (13) | 0.0031 (7) | −0.0005 (10) | −0.0012 (9) |
C1 | 0.0265 (12) | 0.0282 (11) | 0.0286 (12) | −0.0019 (9) | 0.0020 (10) | 0.0052 (10) |
C2 | 0.0259 (12) | 0.0275 (11) | 0.0218 (11) | 0.0008 (9) | 0.0017 (9) | 0.0031 (9) |
C3 | 0.0330 (12) | 0.0256 (11) | 0.0295 (12) | 0.0012 (10) | 0.0017 (11) | 0.0049 (10) |
C4 | 0.0277 (12) | 0.0389 (13) | 0.0304 (12) | 0.0079 (11) | 0.0035 (10) | 0.0054 (10) |
C5 | 0.0225 (12) | 0.0441 (14) | 0.0275 (12) | −0.0040 (11) | −0.0015 (10) | 0.0027 (10) |
C6 | 0.0271 (12) | 0.0319 (11) | 0.0232 (12) | −0.0049 (10) | 0.0009 (9) | −0.0004 (9) |
C7 | 0.0273 (12) | 0.0274 (11) | 0.0172 (10) | 0.0000 (9) | 0.0020 (8) | 0.0015 (9) |
C8 | 0.0306 (12) | 0.0223 (11) | 0.0257 (11) | 0.0023 (9) | 0.0014 (9) | 0.0008 (9) |
C9 | 0.0266 (12) | 0.0314 (12) | 0.0268 (12) | 0.0025 (10) | 0.0041 (10) | −0.0020 (9) |
C10 | 0.0313 (14) | 0.0399 (14) | 0.0420 (15) | 0.0095 (11) | 0.0036 (11) | −0.0004 (12) |
O1—C1 | 1.321 (3) | C5—H5A | 0.9500 |
O1—C9 | 1.452 (3) | C6—C7 | 1.375 (3) |
O2—C1 | 1.206 (3) | C6—H6A | 0.9500 |
O3—C3 | 1.339 (3) | C7—C8 | 1.485 (3) |
O3—H3 | 0.8400 | C8—C9 | 1.500 (3) |
C1—C2 | 1.453 (3) | C8—H8A | 0.9900 |
C2—C3 | 1.388 (3) | C8—H8B | 0.9900 |
C2—C7 | 1.396 (3) | C9—C10 | 1.496 (3) |
C3—C4 | 1.382 (3) | C9—H9A | 1.0000 |
C4—C5 | 1.358 (4) | C10—H10A | 0.9800 |
C4—H4A | 0.9500 | C10—H10B | 0.9800 |
C5—C6 | 1.372 (3) | C10—H10C | 0.9800 |
C1—O1—C9 | 119.58 (17) | C6—C7—C8 | 123.3 (2) |
C3—O3—H3 | 109.5 | C2—C7—C8 | 117.1 (2) |
O2—C1—O1 | 118.1 (2) | C7—C8—C9 | 110.53 (18) |
O2—C1—C2 | 123.0 (2) | C7—C8—H8A | 109.5 |
O1—C1—C2 | 118.9 (2) | C9—C8—H8A | 109.5 |
C3—C2—C7 | 119.6 (2) | C7—C8—H8B | 109.5 |
C3—C2—C1 | 119.7 (2) | C9—C8—H8B | 109.5 |
C7—C2—C1 | 120.7 (2) | H8A—C8—H8B | 108.1 |
O3—C3—C4 | 118.1 (2) | O1—C9—C10 | 105.75 (19) |
O3—C3—C2 | 122.1 (2) | O1—C9—C8 | 109.97 (18) |
C4—C3—C2 | 119.8 (2) | C10—C9—C8 | 113.7 (2) |
C5—C4—C3 | 119.6 (2) | O1—C9—H9A | 109.1 |
C5—C4—H4A | 120.2 | C10—C9—H9A | 109.1 |
C3—C4—H4A | 120.2 | C8—C9—H9A | 109.1 |
C4—C5—C6 | 121.7 (2) | C9—C10—H10A | 109.5 |
C4—C5—H5A | 119.2 | C9—C10—H10B | 109.5 |
C6—C5—H5A | 119.2 | H10A—C10—H10B | 109.5 |
C5—C6—C7 | 119.7 (2) | C9—C10—H10C | 109.5 |
C5—C6—H6A | 120.2 | H10A—C10—H10C | 109.5 |
C7—C6—H6A | 120.2 | H10B—C10—H10C | 109.5 |
C6—C7—C2 | 119.6 (2) | ||
C9—O1—C1—O2 | 167.2 (2) | C4—C5—C6—C7 | 1.2 (4) |
C9—O1—C1—C2 | −14.2 (3) | C5—C6—C7—C2 | 0.1 (3) |
O2—C1—C2—C3 | −8.5 (4) | C5—C6—C7—C8 | −177.9 (2) |
O1—C1—C2—C3 | 172.9 (2) | C3—C2—C7—C6 | −2.4 (3) |
O2—C1—C2—C7 | 168.5 (2) | C1—C2—C7—C6 | −179.3 (2) |
O1—C1—C2—C7 | −10.1 (3) | C3—C2—C7—C8 | 175.7 (2) |
C7—C2—C3—O3 | −175.6 (2) | C1—C2—C7—C8 | −1.2 (3) |
C1—C2—C3—O3 | 1.4 (4) | C6—C7—C8—C9 | −148.7 (2) |
C7—C2—C3—C4 | 3.4 (3) | C2—C7—C8—C9 | 33.3 (3) |
C1—C2—C3—C4 | −179.6 (2) | C1—O1—C9—C10 | 169.77 (19) |
O3—C3—C4—C5 | 176.9 (2) | C1—O1—C9—C8 | 46.6 (3) |
C2—C3—C4—C5 | −2.2 (4) | C7—C8—C9—O1 | −54.2 (2) |
C3—C4—C5—C6 | −0.2 (4) | C7—C8—C9—C10 | −172.56 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2 | 0.84 | 1.84 | 2.572 (2) | 145 |
C4—H4A···O1i | 0.95 | 2.50 | 3.285 (3) | 140 |
Symmetry code: (i) x+1/2, −y+1/2, −z+1. |
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