Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033344/ac2033sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033344/ac2033Isup2.hkl |
CCDC reference: 620508
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.052
- wR factor = 0.169
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.62 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C5 - C11 .. 5.33 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C10 - C11 .. 5.79 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O6 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C17 - C18 ... 1.40 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 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 5 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: APEX2 Software Suite (Bruker, 2005); cell refinement: APEX2 Software Suite; data reduction: APEX2 Software Suite; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C18H14O6 | Dx = 1.455 Mg m−3 |
Mr = 326.29 | Melting point: 473-474K K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
a = 14.6082 (5) Å | Cell parameters from 1783 reflections |
b = 13.5438 (6) Å | θ = 2.8–21.7° |
c = 7.6388 (3) Å | µ = 0.11 mm−1 |
β = 99.838 (2)° | T = 296 K |
V = 1489.12 (10) Å3 | Plate, yellow |
Z = 4 | 0.49 × 0.38 × 0.03 mm |
F(000) = 680 |
Bruker APEX2 CCD diffractometer | 3395 independent reflections |
Radiation source: fine-focus sealed tube | 1637 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
φ and ω scans | θmax = 27.5°, θmin = 1.4° |
Absorption correction: multi-scan APEX2 Software Suite (Bruker, 2005) | h = −18→18 |
Tmin = 0.948, Tmax = 0.997 | k = −17→15 |
9711 measured reflections | l = −9→9 |
Refinement on F2 | 1 restraint |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.053 | w = 1/[σ2(Fo2) + (0.0764P)2 + 0.163P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.169 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.28 e Å−3 |
3395 reflections | Δρmin = −0.22 e Å−3 |
220 parameters |
Experimental. IR (KBr, ν cm-1): 3086.0, 2985.3, 1623.1, 1610.0 (C=O), 1308.2 1H NMR (DMSO-d6, p.p.m.): δ 2.42 (s, 3H, Ph—CH3), 2.76 (dd, 1H, J = 2.8 and 4.8 Hz, –CH2), 2.88 (t, 1H, J = 4.8 Hz, –CH2), 3.37–3.39 (m, 1H, –CH), 4.05 (dd, 1H, J = 6.0 and 11.2 Hz, O—CH2), 4.59 (dd, 1H, J = 2.8 and 11.2 Hz, O—CH2), 6.90–7.52 (s, 4H, ArH), 11.94 (s, 1H, –OH), 12.14 (s, 1H, –OH) 13C NMR (DMSO-d6, p.p.m.): δ 21.36 (C1), 43.24 (C18), 49.21 (C17), 68.49(C16), 107.35 (C13), 108.24 (C15), 110.15 (C10), 113.32 (C4), 120.55 (C7), 124.43 (C5), 132.88 (C3), 134.86 (C2), 148.57 (C9), 161.65 (C12), 164.42(C14), 165.53 (C6), 181.16 (C11), 190.08 (C8) ESI-MS (m/z): 327.3 [M+H]+ |
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 | 0.46463 (19) | 0.3877 (2) | 1.3686 (4) | 0.0884 (10) | |
H1A | 0.5218 | 0.3585 | 1.4261 | 0.133* | |
H1B | 0.4385 | 0.4265 | 1.4529 | 0.133* | |
H1C | 0.4765 | 0.4293 | 1.2731 | 0.133* | |
O1 | 0.38227 (12) | 0.04110 (14) | 1.2995 (3) | 0.0781 (6) | |
H1D | 0.3418 | 0.0034 | 1.2508 | 0.117* | |
C2 | 0.39748 (17) | 0.3076 (2) | 1.2958 (3) | 0.0639 (7) | |
O2 | 0.23293 (11) | −0.00780 (12) | 1.0879 (2) | 0.0679 (5) | |
C3 | 0.41763 (16) | 0.2095 (2) | 1.3302 (3) | 0.0633 (7) | |
H3A | 0.4731 | 0.1925 | 1.4030 | 0.076* | |
O3 | 0.14431 (11) | 0.37623 (12) | 0.9731 (2) | 0.0647 (5) | |
C4 | 0.35678 (16) | 0.13534 (19) | 1.2584 (3) | 0.0574 (7) | |
O4 | 0.08817 (12) | −0.05952 (11) | 0.8667 (2) | 0.0654 (5) | |
H4A | 0.1354 | −0.0677 | 0.9403 | 0.098* | |
C5 | 0.27311 (14) | 0.15919 (17) | 1.1467 (3) | 0.0475 (6) | |
O5 | −0.11594 (11) | 0.19488 (12) | 0.6149 (2) | 0.0646 (5) | |
C6 | 0.25189 (15) | 0.25950 (17) | 1.1162 (3) | 0.0466 (6) | |
O6 | −0.32713 (16) | 0.2086 (2) | 0.4851 (4) | 0.1286 (10) | |
C7 | 0.31302 (16) | 0.33179 (18) | 1.1897 (3) | 0.0557 (6) | |
H7A | 0.2977 | 0.3978 | 1.1682 | 0.067* | |
C8 | 0.16372 (15) | 0.28949 (17) | 0.9998 (3) | 0.0484 (6) | |
C9 | 0.10153 (14) | 0.20974 (15) | 0.9153 (3) | 0.0433 (5) | |
C10 | 0.12678 (14) | 0.10929 (15) | 0.9432 (3) | 0.0440 (6) | |
C11 | 0.21144 (15) | 0.08193 (18) | 1.0607 (3) | 0.0512 (6) | |
C12 | 0.06866 (16) | 0.03780 (16) | 0.8511 (3) | 0.0489 (6) | |
C13 | −0.01326 (16) | 0.06352 (17) | 0.7398 (3) | 0.0523 (6) | |
H13A | −0.0515 | 0.0150 | 0.6803 | 0.063* | |
C14 | −0.03722 (15) | 0.16138 (18) | 0.7184 (3) | 0.0504 (6) | |
C15 | 0.02051 (15) | 0.23510 (17) | 0.8053 (3) | 0.0501 (6) | |
H15A | 0.0040 | 0.3012 | 0.7885 | 0.060* | |
C16 | −0.17566 (17) | 0.12453 (19) | 0.5133 (3) | 0.0664 (7) | |
H16A | −0.2007 | 0.0793 | 0.5915 | 0.080* | |
H16B | −0.1415 | 0.0867 | 0.4380 | 0.080* | |
C17 | −0.2513 (2) | 0.1803 (2) | 0.4042 (4) | 0.0886 (10) | |
H17A | −0.2316 | 0.2293 | 0.3239 | 0.106* | |
C18 | −0.3393 (2) | 0.1388 (3) | 0.3467 (5) | 0.1129 (12) | |
H18A | −0.3486 | 0.0704 | 0.3772 | 0.135* | |
H18B | −0.3731 | 0.1594 | 0.2320 | 0.135* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0724 (19) | 0.103 (2) | 0.083 (2) | −0.0322 (17) | −0.0045 (17) | −0.0038 (18) |
O1 | 0.0640 (12) | 0.0778 (14) | 0.0856 (15) | 0.0167 (10) | −0.0068 (10) | 0.0043 (11) |
C2 | 0.0540 (15) | 0.088 (2) | 0.0501 (16) | −0.0156 (14) | 0.0095 (13) | −0.0074 (14) |
O2 | 0.0693 (11) | 0.0491 (11) | 0.0793 (13) | 0.0111 (9) | −0.0044 (10) | 0.0015 (9) |
C3 | 0.0427 (13) | 0.091 (2) | 0.0536 (17) | 0.0005 (14) | 0.0011 (12) | −0.0022 (15) |
O3 | 0.0662 (11) | 0.0463 (11) | 0.0770 (13) | −0.0007 (8) | −0.0006 (9) | 0.0010 (9) |
C4 | 0.0500 (14) | 0.0659 (17) | 0.0564 (16) | 0.0113 (13) | 0.0091 (12) | 0.0014 (13) |
O4 | 0.0704 (12) | 0.0446 (10) | 0.0758 (14) | 0.0008 (8) | −0.0030 (9) | −0.0053 (8) |
C5 | 0.0413 (12) | 0.0526 (15) | 0.0486 (14) | 0.0016 (10) | 0.0080 (11) | −0.0023 (11) |
O5 | 0.0514 (10) | 0.0658 (12) | 0.0692 (12) | 0.0024 (8) | −0.0102 (9) | −0.0024 (9) |
C6 | 0.0459 (12) | 0.0526 (14) | 0.0423 (14) | −0.0030 (11) | 0.0104 (11) | −0.0036 (11) |
O6 | 0.0808 (15) | 0.148 (2) | 0.144 (2) | 0.0367 (15) | −0.0195 (16) | −0.0498 (18) |
C7 | 0.0568 (14) | 0.0581 (16) | 0.0521 (15) | −0.0107 (12) | 0.0092 (12) | −0.0039 (12) |
C8 | 0.0516 (13) | 0.0467 (15) | 0.0478 (14) | 0.0018 (11) | 0.0115 (11) | −0.0001 (11) |
C9 | 0.0422 (12) | 0.0433 (13) | 0.0446 (14) | 0.0012 (10) | 0.0077 (11) | −0.0004 (10) |
C10 | 0.0439 (12) | 0.0439 (14) | 0.0438 (13) | 0.0021 (10) | 0.0068 (11) | −0.0003 (10) |
C11 | 0.0548 (14) | 0.0487 (15) | 0.0518 (15) | 0.0063 (12) | 0.0141 (12) | 0.0021 (11) |
C12 | 0.0547 (14) | 0.0411 (13) | 0.0510 (15) | −0.0008 (11) | 0.0091 (12) | −0.0010 (11) |
C13 | 0.0510 (14) | 0.0497 (15) | 0.0543 (15) | −0.0066 (11) | 0.0038 (12) | −0.0064 (11) |
C14 | 0.0462 (13) | 0.0549 (16) | 0.0489 (14) | 0.0016 (11) | 0.0044 (11) | −0.0014 (11) |
C15 | 0.0512 (13) | 0.0435 (14) | 0.0550 (16) | 0.0015 (11) | 0.0078 (12) | −0.0010 (11) |
C16 | 0.0537 (15) | 0.079 (2) | 0.0614 (17) | −0.0019 (13) | −0.0058 (13) | −0.0075 (14) |
C17 | 0.0673 (18) | 0.115 (3) | 0.075 (2) | −0.0032 (19) | −0.0120 (17) | 0.0018 (18) |
C18 | 0.084 (2) | 0.128 (3) | 0.112 (3) | 0.002 (2) | −0.028 (2) | −0.008 (2) |
C1—C2 | 1.504 (4) | O6—C18 | 1.407 (4) |
C1—H1A | 0.9600 | O6—C17 | 1.410 (4) |
C1—H1B | 0.9600 | C7—H7A | 0.9300 |
C1—H1C | 0.9600 | C8—C9 | 1.486 (3) |
O1—C4 | 1.352 (3) | C9—C15 | 1.373 (3) |
O1—H1D | 0.8200 | C9—C10 | 1.416 (3) |
C2—C3 | 1.377 (3) | C10—C12 | 1.396 (3) |
C2—C7 | 1.394 (3) | C10—C11 | 1.447 (3) |
O2—C11 | 1.263 (3) | C12—C13 | 1.389 (3) |
C3—C4 | 1.391 (3) | C13—C14 | 1.373 (3) |
C3—H3A | 0.9300 | C13—H13A | 0.9300 |
O3—C8 | 1.218 (2) | C14—C15 | 1.399 (3) |
C4—C5 | 1.403 (3) | C15—H15A | 0.9300 |
O4—C12 | 1.350 (3) | C16—C17 | 1.474 (4) |
O4—H4A | 0.8200 | C16—H16A | 0.9700 |
C5—C6 | 1.404 (3) | C16—H16B | 0.9700 |
C5—C11 | 1.462 (3) | C17—C18 | 1.402 (4) |
O5—C14 | 1.358 (3) | C17—H17A | 0.9800 |
O5—C16 | 1.428 (3) | C18—H18A | 0.9700 |
C6—C7 | 1.379 (3) | C18—H18B | 0.9700 |
C6—C8 | 1.491 (3) | ||
C2—C1—H1A | 109.5 | C12—C10—C11 | 121.1 (2) |
C2—C1—H1B | 109.5 | C9—C10—C11 | 120.8 (2) |
H1A—C1—H1B | 109.5 | O2—C11—C10 | 120.7 (2) |
C2—C1—H1C | 109.5 | O2—C11—C5 | 119.9 (2) |
H1A—C1—H1C | 109.5 | C10—C11—C5 | 119.4 (2) |
H1B—C1—H1C | 109.5 | O4—C12—C13 | 116.5 (2) |
C4—O1—H1D | 109.5 | O4—C12—C10 | 122.1 (2) |
C3—C2—C7 | 118.5 (2) | C13—C12—C10 | 121.4 (2) |
C3—C2—C1 | 121.4 (3) | C14—C13—C12 | 119.4 (2) |
C7—C2—C1 | 120.1 (3) | C14—C13—H13A | 120.3 |
C2—C3—C4 | 121.4 (2) | C12—C13—H13A | 120.3 |
C2—C3—H3A | 119.3 | O5—C14—C13 | 124.4 (2) |
C4—C3—H3A | 119.3 | O5—C14—C15 | 114.8 (2) |
O1—C4—C3 | 117.3 (2) | C13—C14—C15 | 120.8 (2) |
O1—C4—C5 | 122.4 (2) | C9—C15—C14 | 119.9 (2) |
C3—C4—C5 | 120.3 (2) | C9—C15—H15A | 120.1 |
C12—O4—H4A | 109.5 | C14—C15—H15A | 120.1 |
C4—C5—C6 | 117.9 (2) | O5—C16—C17 | 107.2 (2) |
C4—C5—C11 | 121.0 (2) | O5—C16—H16A | 110.3 |
C6—C5—C11 | 121.1 (2) | C17—C16—H16A | 110.3 |
C14—O5—C16 | 118.14 (19) | O5—C16—H16B | 110.3 |
C7—C6—C5 | 120.7 (2) | C17—C16—H16B | 110.3 |
C7—C6—C8 | 118.9 (2) | H16A—C16—H16B | 108.5 |
C5—C6—C8 | 120.4 (2) | C18—C17—O6 | 60.0 (2) |
C18—O6—C17 | 59.7 (2) | C18—C17—C16 | 122.0 (3) |
C6—C7—C2 | 121.2 (2) | O6—C17—C16 | 117.4 (3) |
C6—C7—H7A | 119.4 | C18—C17—H17A | 115.3 |
C2—C7—H7A | 119.4 | O6—C17—H17A | 115.3 |
O3—C8—C9 | 121.4 (2) | C16—C17—H17A | 115.3 |
O3—C8—C6 | 121.0 (2) | C17—C18—O6 | 60.3 (2) |
C9—C8—C6 | 117.6 (2) | C17—C18—H18A | 117.7 |
C15—C9—C10 | 120.5 (2) | O6—C18—H18A | 117.7 |
C15—C9—C8 | 118.9 (2) | C17—C18—H18B | 117.7 |
C10—C9—C8 | 120.6 (2) | O6—C18—H18B | 117.7 |
C12—C10—C9 | 118.0 (2) | H18A—C18—H18B | 114.9 |
C7—C2—C3—C4 | 1.4 (3) | C12—C10—C11—O2 | −2.8 (3) |
C1—C2—C3—C4 | −178.0 (2) | C9—C10—C11—O2 | 178.69 (19) |
C2—C3—C4—O1 | −179.9 (2) | C12—C10—C11—C5 | 176.47 (19) |
C2—C3—C4—C5 | 0.6 (3) | C9—C10—C11—C5 | −2.1 (3) |
O1—C4—C5—C6 | 178.3 (2) | C4—C5—C11—O2 | 0.7 (3) |
C3—C4—C5—C6 | −2.3 (3) | C6—C5—C11—O2 | 178.7 (2) |
O1—C4—C5—C11 | −3.6 (3) | C4—C5—C11—C10 | −178.59 (19) |
C3—C4—C5—C11 | 175.8 (2) | C6—C5—C11—C10 | −0.5 (3) |
C4—C5—C6—C7 | 1.9 (3) | C9—C10—C12—O4 | 178.63 (19) |
C11—C5—C6—C7 | −176.21 (19) | C11—C10—C12—O4 | 0.1 (3) |
C4—C5—C6—C8 | −179.58 (18) | C9—C10—C12—C13 | −2.2 (3) |
C11—C5—C6—C8 | 2.3 (3) | C11—C10—C12—C13 | 179.2 (2) |
C5—C6—C7—C2 | 0.2 (3) | O4—C12—C13—C14 | 179.88 (19) |
C8—C6—C7—C2 | −178.37 (19) | C10—C12—C13—C14 | 0.7 (3) |
C3—C2—C7—C6 | −1.8 (3) | C16—O5—C14—C13 | −3.6 (3) |
C1—C2—C7—C6 | 177.6 (2) | C16—O5—C14—C15 | 176.23 (19) |
C7—C6—C8—O3 | −1.9 (3) | C12—C13—C14—O5 | −179.2 (2) |
C5—C6—C8—O3 | 179.6 (2) | C12—C13—C14—C15 | 0.9 (3) |
C7—C6—C8—C9 | 176.98 (18) | C10—C9—C15—C14 | −0.7 (3) |
C5—C6—C8—C9 | −1.5 (3) | C8—C9—C15—C14 | 177.36 (18) |
O3—C8—C9—C15 | −0.2 (3) | O5—C14—C15—C9 | 179.21 (18) |
C6—C8—C9—C15 | −179.01 (18) | C13—C14—C15—C9 | −0.9 (3) |
O3—C8—C9—C10 | 177.9 (2) | C14—O5—C16—C17 | −175.9 (2) |
C6—C8—C9—C10 | −1.0 (3) | C18—O6—C17—C16 | −113.0 (3) |
C15—C9—C10—C12 | 2.2 (3) | O5—C16—C17—C18 | −153.2 (3) |
C8—C9—C10—C12 | −175.80 (19) | O5—C16—C17—O6 | −83.0 (3) |
C15—C9—C10—C11 | −179.23 (18) | C16—C17—C18—O6 | 105.4 (3) |
C8—C9—C10—C11 | 2.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1D···O2 | 0.82 | 1.85 | 2.570 (2) | 146 |
O4—H4A···O2 | 0.82 | 1.85 | 2.569 (2) | 146 |
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