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O hydrogen bond, with OO separations of 2.483 (4) and 2.468 (4) Å.Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100006612/qa0296sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S0108270100006612/qa0296Isup2.hkl |
CCDC reference: 146103
Data collection: P3/P4-PC Diffractometer Control Program(Siemens, 1991); cell refinement: P3/P4-PC Diffractometer Control Program; data reduction: P3/P4-PC Diffractometer Control Program; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 1994); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.
| C10H12O2 | F(000) = 352 |
| Mr = 164.20 | Dx = 1.234 Mg m−3 |
| Triclinic, P1 | Melting point: 328 K |
| a = 7.431 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 7.604 (3) Å | Cell parameters from 50 reflections |
| c = 16.007 (6) Å | θ = 8.1–13.3° |
| α = 93.61 (3)° | µ = 0.09 mm−1 |
| β = 95.50 (4)° | T = 293 K |
| γ = 99.89 (4)° | Parallelepiped, pale yellow |
| V = 884.0 (7) Å3 | 0.30 × 0.20 × 0.10 mm |
| Z = 4 |
| Nicolet R3m/V diffractometer | Rint = 0.004 |
| Radiation source: fine-focus sealed tube | θmax = 25.6°, θmin = 2.6° |
| Graphite monochromator | h = 0→8 |
| ω–2θ scans | k = −8→8 |
| 2932 measured reflections | l = −19→19 |
| 2917 independent reflections | 2 standard reflections every 150 reflections |
| 1334 reflections with I > 2σ(I) | intensity decay: none |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
| wR(F2) = 0.147 | w = 1/[σ2(Fo2) + (0.1115P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 0.91 | (Δ/σ)max < 0.001 |
| 2917 reflections | Δρmax = 0.27 e Å−3 |
| 218 parameters | Δρmin = −0.21 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: direct methods | Extinction coefficient: 0.0725 (89) |
Experimental. The data completeness is affected by the omission of the very negative intensities, which generally lie in the outer shell of the data. |
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2σ(F2) is used only for calculating the R factors for observed reflections 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 | 0.1494 (4) | 0.1435 (4) | −0.0420 (2) | 0.0925 (10) | |
| O2 | 0.2942 (4) | 0.2305 (3) | 0.1044 (2) | 0.0785 (9) | |
| H2A | 0.2454 (4) | 0.1626 (3) | 0.0636 (2) | 0.118* | |
| C1 | 0.2465 (4) | 0.4467 (4) | 0.0032 (2) | 0.0494 (9) | |
| C2 | 0.3099 (5) | 0.4015 (4) | 0.0839 (2) | 0.0538 (9) | |
| C3 | 0.3904 (5) | 0.5317 (5) | 0.1472 (2) | 0.0581 (10) | |
| H3A | 0.4294 (5) | 0.4978 (5) | 0.1998 (2) | 0.070* | |
| C4 | 0.4133 (5) | 0.7091 (5) | 0.1333 (2) | 0.0581 (10) | |
| C5 | 0.3550 (5) | 0.7559 (4) | 0.0548 (2) | 0.0572 (9) | |
| H5A | 0.3718 (5) | 0.8767 (4) | 0.0453 (2) | 0.069* | |
| C6 | 0.2729 (4) | 0.6320 (4) | −0.0107 (2) | 0.0503 (9) | |
| C7 | 0.1599 (5) | 0.3000 (5) | −0.0605 (2) | 0.0609 (10) | |
| C8 | 0.0814 (6) | 0.3244 (6) | −0.1471 (2) | 0.0829 (13) | |
| H8A | 0.0332 (6) | 0.2094 (6) | −0.1764 (2) | 0.124* | |
| H8B | 0.1758 (6) | 0.3870 (6) | −0.1767 (2) | 0.124* | |
| H8C | −0.0156 (6) | 0.3926 (6) | −0.1440 (2) | 0.124* | |
| C9 | 0.2185 (6) | 0.7077 (5) | −0.0924 (2) | 0.0730 (12) | |
| H9A | 0.1631 (6) | 0.6115 (5) | −0.1336 (2) | 0.109* | |
| H9B | 0.3256 (6) | 0.7740 (5) | −0.1124 (2) | 0.109* | |
| H9C | 0.1321 (6) | 0.7856 (5) | −0.0833 (2) | 0.109* | |
| C10 | 0.4975 (6) | 0.8525 (6) | 0.2016 (3) | 0.0897 (14) | |
| H10A | 0.5020 (6) | 0.9680 (6) | 0.1800 (3) | 0.135* | |
| H10B | 0.6198 (6) | 0.8365 (6) | 0.2203 (3) | 0.135* | |
| H10C | 0.4245 (6) | 0.8448 (6) | 0.2480 (3) | 0.135* | |
| O1' | −0.2981 (4) | −0.4972 (4) | −0.6728 (2) | 0.0899 (10) | |
| O2' | −0.1634 (4) | −0.2149 (3) | −0.5879 (2) | 0.0765 (9) | |
| H2'A | −0.2048 (4) | −0.2811 (3) | −0.6303 (2) | 0.115* | |
| C1' | −0.2504 (4) | −0.4940 (4) | −0.5254 (2) | 0.0493 (9) | |
| C2' | −0.1758 (4) | −0.3095 (4) | −0.5195 (2) | 0.0507 (9) | |
| C3' | −0.1112 (5) | −0.2154 (4) | −0.4435 (2) | 0.0550 (9) | |
| H3'A | −0.0606 (5) | −0.0945 (4) | −0.4422 (2) | 0.066* | |
| C4' | −0.1196 (5) | −0.2961 (5) | −0.3693 (2) | 0.0602 (10) | |
| C5' | −0.1900 (5) | −0.4783 (5) | −0.3742 (2) | 0.0647 (10) | |
| H5'A | −0.1937 (5) | −0.5353 (5) | −0.3246 (2) | 0.078* | |
| C6' | −0.2547 (5) | −0.5791 (5) | −0.4493 (2) | 0.0548 (9) | |
| C7' | −0.3147 (5) | −0.5818 (5) | −0.6111 (3) | 0.0652 (11) | |
| C8' | −0.4068 (6) | −0.7731 (5) | −0.6289 (3) | 0.0939 (15) | |
| H8'A | −0.4359 (6) | −0.7998 (5) | −0.6886 (3) | 0.141* | |
| H8'B | −0.5177 (6) | −0.7929 (5) | −0.6020 (3) | 0.141* | |
| H8'C | −0.3258 (6) | −0.8496 (5) | −0.6076 (3) | 0.141* | |
| C9' | −0.3248 (6) | −0.7755 (5) | −0.4426 (3) | 0.0904 (14) | |
| H9'A | −0.3664 (6) | −0.8334 (5) | −0.4977 (3) | 0.136* | |
| H9'B | −0.4250 (6) | −0.7886 (5) | −0.4084 (3) | 0.136* | |
| H9'C | −0.2276 (6) | −0.8295 (5) | −0.4172 (3) | 0.136* | |
| C10' | −0.0510 (7) | −0.1904 (6) | −0.2870 (2) | 0.0950 (15) | |
| H10D | −0.0672 (7) | −0.2673 (6) | −0.2419 (2) | 0.142* | |
| H10E | −0.1188 (7) | −0.0949 (6) | −0.2796 (2) | 0.142* | |
| H10F | 0.0771 (7) | −0.1413 (6) | −0.2865 (2) | 0.142* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.118 (3) | 0.050 (2) | 0.104 (2) | 0.006 (2) | 0.012 (2) | −0.007 (2) |
| O2 | 0.101 (2) | 0.055 (2) | 0.086 (2) | 0.0216 (14) | 0.016 (2) | 0.0219 (14) |
| C1 | 0.046 (2) | 0.050 (2) | 0.055 (2) | 0.012 (2) | 0.009 (2) | 0.005 (2) |
| C2 | 0.056 (2) | 0.048 (2) | 0.062 (2) | 0.016 (2) | 0.011 (2) | 0.013 (2) |
| C3 | 0.059 (2) | 0.074 (3) | 0.046 (2) | 0.024 (2) | 0.009 (2) | 0.009 (2) |
| C4 | 0.054 (2) | 0.064 (2) | 0.058 (2) | 0.016 (2) | 0.006 (2) | −0.005 (2) |
| C5 | 0.065 (2) | 0.044 (2) | 0.065 (2) | 0.013 (2) | 0.011 (2) | 0.002 (2) |
| C6 | 0.046 (2) | 0.053 (2) | 0.056 (2) | 0.015 (2) | 0.010 (2) | 0.010 (2) |
| C7 | 0.053 (2) | 0.061 (2) | 0.070 (3) | 0.011 (2) | 0.014 (2) | −0.005 (2) |
| C8 | 0.078 (3) | 0.095 (3) | 0.069 (3) | 0.012 (2) | −0.003 (2) | −0.022 (2) |
| C9 | 0.089 (3) | 0.072 (3) | 0.061 (2) | 0.023 (2) | 0.001 (2) | 0.015 (2) |
| C10 | 0.103 (4) | 0.082 (3) | 0.076 (3) | 0.009 (3) | −0.003 (3) | −0.019 (2) |
| O1' | 0.107 (2) | 0.092 (2) | 0.058 (2) | −0.003 (2) | −0.013 (2) | 0.000 (2) |
| O2' | 0.102 (2) | 0.061 (2) | 0.061 (2) | 0.0018 (14) | −0.0032 (14) | 0.0190 (13) |
| C1' | 0.036 (2) | 0.051 (2) | 0.059 (2) | 0.006 (2) | 0.002 (2) | 0.004 (2) |
| C2' | 0.049 (2) | 0.048 (2) | 0.055 (2) | 0.008 (2) | 0.003 (2) | 0.010 (2) |
| C3' | 0.057 (2) | 0.045 (2) | 0.059 (2) | 0.003 (2) | 0.003 (2) | 0.000 (2) |
| C4' | 0.058 (2) | 0.070 (3) | 0.053 (2) | 0.014 (2) | 0.003 (2) | 0.002 (2) |
| C5' | 0.067 (3) | 0.075 (3) | 0.058 (2) | 0.016 (2) | 0.016 (2) | 0.025 (2) |
| C6' | 0.044 (2) | 0.052 (2) | 0.072 (3) | 0.010 (2) | 0.014 (2) | 0.014 (2) |
| C7' | 0.047 (2) | 0.066 (3) | 0.077 (3) | 0.008 (2) | −0.007 (2) | −0.009 (2) |
| C8' | 0.081 (3) | 0.070 (3) | 0.115 (4) | −0.006 (2) | −0.012 (3) | −0.023 (3) |
| C9' | 0.088 (3) | 0.061 (3) | 0.123 (4) | 0.004 (2) | 0.020 (3) | 0.028 (3) |
| C10' | 0.104 (4) | 0.114 (4) | 0.063 (3) | 0.017 (3) | 0.007 (3) | −0.010 (3) |
| O1—C7 | 1.236 (4) | O1'—C7' | 1.217 (4) |
| O2—C2 | 1.350 (4) | O2'—C2' | 1.349 (4) |
| C1—C2 | 1.414 (4) | C1'—C2' | 1.411 (4) |
| C1—C6 | 1.423 (4) | C1'—C6' | 1.415 (5) |
| C1—C7 | 1.478 (5) | C1'—C7' | 1.485 (5) |
| C2—C3 | 1.386 (5) | C2'—C3' | 1.373 (5) |
| C3—C4 | 1.366 (5) | C3'—C4' | 1.372 (5) |
| C4—C5 | 1.378 (5) | C4'—C5' | 1.389 (5) |
| C4—C10 | 1.503 (5) | C4'—C10' | 1.497 (5) |
| C5—C6 | 1.383 (5) | C5'—C6' | 1.382 (5) |
| C6—C9 | 1.510 (4) | C6'—C9' | 1.509 (5) |
| C7—C8 | 1.486 (5) | C7'—C8' | 1.495 (5) |
| C2—C1—C6 | 117.1 (3) | C2'—C1'—C6' | 117.1 (3) |
| C2—C1—C7 | 118.3 (3) | C2'—C1'—C7' | 116.9 (3) |
| C6—C1—C7 | 124.7 (3) | C6'—C1'—C7' | 125.9 (3) |
| O2—C2—C3 | 115.8 (3) | O2'—C2'—C3' | 116.0 (3) |
| O2—C2—C1 | 122.5 (3) | O2'—C2'—C1' | 122.3 (3) |
| C3—C2—C1 | 121.6 (3) | C3'—C2'—C1' | 121.8 (3) |
| C4—C3—C2 | 120.7 (3) | C4'—C3'—C2' | 121.4 (3) |
| C3—C4—C5 | 118.5 (3) | C3'—C4'—C5' | 117.5 (4) |
| C3—C4—C10 | 121.6 (4) | C3'—C4'—C10' | 120.5 (4) |
| C5—C4—C10 | 119.8 (4) | C5'—C4'—C10' | 122.0 (4) |
| C4—C5—C6 | 123.3 (3) | C6'—C5'—C4' | 123.2 (3) |
| C5—C6—C1 | 118.7 (3) | C5'—C6'—C1' | 119.0 (3) |
| C5—C6—C9 | 116.0 (3) | C5'—C6'—C9' | 115.9 (4) |
| C1—C6—C9 | 125.3 (3) | C1'—C6'—C9' | 125.1 (4) |
| O1—C7—C1 | 119.0 (4) | O1'—C7'—C1' | 120.6 (4) |
| O1—C7—C8 | 115.9 (4) | O1'—C7'—C8' | 115.1 (4) |
| C1—C7—C8 | 125.1 (3) | C1'—C7'—C8' | 124.3 (4) |
