Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001964/ww6006sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001964/ww6006Isup2.hkl |
CCDC reference: 182606
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.095
- Data-to-parameter ratio = 18.0
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The title compound was prepared by base-catalyzed hydrolysis of the parent ethyl ester (26a) as previously described (Greatrex et al., 2002). Crystals suitable for X-ray analysis were grown by slow evaporation from an ethyl acetate/hexane (1:1) solution of the compound.
The H atoms were included in the riding-model approximation. The torsion angle about the C—O bond of the carboxylic acid group has been refined.
Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL 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).
C11H14O5 | Dx = 1.416 Mg m−3 |
Mr = 226.22 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 25701 reflections |
a = 8.0792 (1) Å | θ = 3–28.3° |
b = 10.6879 (2) Å | µ = 0.11 mm−1 |
c = 24.5704 (5) Å | T = 123 K |
V = 2121.65 (6) Å3 | Tabular, colourless |
Z = 8 | 0.24 × 0.14 × 0.04 mm |
F(000) = 960 |
KappaCCD diffractometer | θmax = 28.3°, θmin = 3.0° |
CCD rotation images, thick slices scans | h = −10→10 |
23956 measured reflections | k = −14→14 |
2630 independent reflections | l = −32→32 |
1847 reflections with I > 2σ(I) |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0434P)2 + 0.2022P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.095 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 0.21 e Å−3 |
2630 reflections | Δρmin = −0.22 e Å−3 |
146 parameters |
C11H14O5 | V = 2121.65 (6) Å3 |
Mr = 226.22 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 8.0792 (1) Å | µ = 0.11 mm−1 |
b = 10.6879 (2) Å | T = 123 K |
c = 24.5704 (5) Å | 0.24 × 0.14 × 0.04 mm |
KappaCCD diffractometer | 2630 independent reflections |
23956 measured reflections | 1847 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.21 e Å−3 |
2630 reflections | Δρmin = −0.22 e Å−3 |
146 parameters |
Experimental. m.p. 128–102°C decomp. IR(nujol) 1776, 1726, 1677, 1377, 1162 cm-1. 1H n.m.r. (600 MHz, CDCl3): δ 1.42–1.48 (m, 1H), 1.73–1.86 (m,3H), 1.88–1.94 (m, 1H), 2.19–2.24 (m, 1H), 2.33–2.37 (m, 1H), 2.42–2.47 (dd,J=12, 14.4 Hz, 1H), 2.73–2.78 (m,1H), 3.01–3.04 (dd,J=3.6, 14.4 Hz, 1H), 3.10–3.16 (m,1H), 3.39 (d,J=12.6 Hz, 1H), 4.18–4.21 (m, 1H). MS (M+,%) 226 (M.+, 10), 208 (27), 153 (22), 125 (23), 124 (88), 95 (40), 68 (55), 41 (100). HRMS Calcd. for C11H14O5: 226.0841; Found: 226.0849. |
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. |
x | y | z | Uiso*/Ueq | ||
C2 | 0.25936 (17) | 0.71910 (12) | 0.39367 (5) | 0.0222 (3) | |
C3 | 0.18115 (16) | 0.76712 (12) | 0.34165 (5) | 0.0195 (3) | |
H2 | 0.2445 | 0.8418 | 0.3287 | 0.023* | |
C3A | 0.00819 (16) | 0.80962 (12) | 0.36046 (5) | 0.0187 (3) | |
H3 | −0.0681 | 0.736 | 0.3604 | 0.022* | |
C4 | −0.06406 (16) | 0.91178 (12) | 0.32415 (5) | 0.0201 (3) | |
H10A | 0.0154 | 0.9823 | 0.3232 | 0.024* | |
H10B | −0.0724 | 0.8783 | 0.2867 | 0.024* | |
C5 | −0.23037 (17) | 0.96266 (12) | 0.33993 (5) | 0.0199 (3) | |
C6 | −0.35421 (17) | 0.88299 (13) | 0.36949 (6) | 0.0238 (3) | |
H8A | −0.3156 | 0.7951 | 0.3698 | 0.029* | |
H8B | −0.4615 | 0.8859 | 0.3501 | 0.029* | |
C7 | −0.37844 (18) | 0.92861 (13) | 0.42852 (6) | 0.0263 (3) | |
H7A | −0.4421 | 1.0078 | 0.4278 | 0.032* | |
H7B | −0.4455 | 0.866 | 0.4484 | 0.032* | |
C8 | −0.21789 (18) | 0.95045 (13) | 0.45991 (5) | 0.0264 (3) | |
H6A | −0.2465 | 0.9724 | 0.4979 | 0.032* | |
H6B | −0.1608 | 1.0236 | 0.4438 | 0.032* | |
C9 | −0.09544 (17) | 0.83986 (13) | 0.46108 (5) | 0.0244 (3) | |
H5A | −0.0458 | 0.8347 | 0.4978 | 0.029* | |
H5B | −0.1577 | 0.7614 | 0.4547 | 0.029* | |
C9A | 0.04278 (16) | 0.84862 (12) | 0.41947 (5) | 0.0212 (3) | |
H4 | 0.0877 | 0.9358 | 0.4196 | 0.025* | |
C10 | 0.17803 (15) | 0.67021 (13) | 0.29689 (5) | 0.0206 (3) | |
O1 | 0.17430 (11) | 0.76198 (9) | 0.43694 (4) | 0.0264 (3) | |
O2 | 0.38100 (12) | 0.65480 (9) | 0.39857 (4) | 0.0287 (3) | |
O3 | −0.26599 (13) | 1.07091 (9) | 0.32865 (4) | 0.0284 (3) | |
O4 | 0.18102 (12) | 0.55878 (9) | 0.30398 (4) | 0.0288 (3) | |
O5 | 0.16712 (14) | 0.72439 (9) | 0.24839 (4) | 0.0329 (3) | |
H5 | 0.1795 | 0.6703 | 0.224 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.0224 (7) | 0.0189 (7) | 0.0252 (7) | −0.0024 (6) | −0.0015 (6) | 0.0006 (6) |
C3 | 0.0194 (7) | 0.0179 (6) | 0.0213 (7) | 0.0005 (5) | −0.0002 (5) | 0.0013 (6) |
C3A | 0.0182 (7) | 0.0176 (6) | 0.0203 (7) | −0.0010 (5) | 0.0005 (6) | 0.0003 (6) |
C4 | 0.0212 (7) | 0.0210 (7) | 0.0182 (7) | −0.0003 (5) | 0.0000 (6) | 0.0016 (5) |
C5 | 0.0230 (7) | 0.0214 (7) | 0.0152 (6) | 0.0015 (6) | −0.0025 (6) | −0.0017 (5) |
C6 | 0.0194 (7) | 0.0247 (7) | 0.0272 (8) | 0.0002 (6) | 0.0007 (6) | 0.0003 (6) |
C7 | 0.0248 (8) | 0.0273 (8) | 0.0268 (8) | 0.0008 (6) | 0.0066 (6) | 0.0019 (6) |
C8 | 0.0328 (9) | 0.0254 (8) | 0.0210 (7) | 0.0004 (6) | 0.0055 (6) | −0.0020 (6) |
C9 | 0.0300 (8) | 0.0253 (8) | 0.0181 (7) | −0.0011 (6) | 0.0002 (6) | 0.0011 (6) |
C9A | 0.0229 (7) | 0.0193 (7) | 0.0214 (7) | 0.0016 (6) | −0.0029 (6) | 0.0004 (6) |
C10 | 0.0154 (7) | 0.0218 (7) | 0.0247 (8) | 0.0016 (6) | 0.0025 (6) | 0.0010 (6) |
O1 | 0.0275 (5) | 0.0295 (6) | 0.0222 (5) | 0.0065 (4) | −0.0028 (4) | 0.0017 (4) |
O2 | 0.0268 (5) | 0.0268 (6) | 0.0325 (6) | 0.0061 (5) | −0.0060 (5) | 0.0024 (4) |
O3 | 0.0336 (6) | 0.0229 (5) | 0.0287 (6) | 0.0078 (4) | 0.0074 (5) | 0.0057 (4) |
O4 | 0.0352 (6) | 0.0182 (5) | 0.0331 (6) | 0.0002 (4) | −0.0007 (5) | −0.0003 (4) |
O5 | 0.0554 (7) | 0.0230 (5) | 0.0205 (5) | 0.0036 (5) | 0.0037 (5) | −0.0017 (4) |
C2—O2 | 1.2052 (16) | C6—H8B | 0.99 |
C2—O1 | 1.3464 (16) | C7—C8 | 1.527 (2) |
C2—C3 | 1.5152 (18) | C7—H7A | 0.99 |
C3—C10 | 1.5110 (18) | C7—H7B | 0.99 |
C3—C3A | 1.5403 (18) | C8—C9 | 1.5416 (19) |
C3—H2 | 1 | C8—H6A | 0.99 |
C3A—C4 | 1.5261 (18) | C8—H6B | 0.99 |
C3A—C9A | 1.5342 (18) | C9—C9A | 1.5169 (18) |
C3A—H3 | 1 | C9—H5A | 0.99 |
C4—C5 | 1.5005 (19) | C9—H5B | 0.99 |
C4—H10A | 0.99 | C9A—O1 | 1.4734 (15) |
C4—H10B | 0.99 | C9A—H4 | 1 |
C5—O3 | 1.2240 (15) | C10—O4 | 1.2040 (15) |
C5—C6 | 1.5013 (19) | C10—O5 | 1.3277 (17) |
C6—C7 | 1.5426 (19) | O5—H5 | 0.84 |
C6—H8A | 0.99 | ||
O2—C2—O1 | 122.10 (12) | C8—C7—C6 | 114.54 (11) |
O2—C2—C3 | 128.13 (12) | C8—C7—H7A | 108.6 |
O1—C2—C3 | 109.75 (11) | C6—C7—H7A | 108.6 |
C10—C3—C2 | 112.87 (11) | C8—C7—H7B | 108.6 |
C10—C3—C3A | 113.92 (10) | C6—C7—H7B | 108.6 |
C2—C3—C3A | 103.02 (10) | H7A—C7—H7B | 107.6 |
C10—C3—H2 | 108.9 | C7—C8—C9 | 115.93 (12) |
C2—C3—H2 | 108.9 | C7—C8—H6A | 108.3 |
C3A—C3—H2 | 108.9 | C9—C8—H6A | 108.3 |
C4—C3A—C9A | 115.33 (11) | C7—C8—H6B | 108.3 |
C4—C3A—C3 | 112.50 (11) | C9—C8—H6B | 108.3 |
C9A—C3A—C3 | 101.44 (10) | H6A—C8—H6B | 107.4 |
C4—C3A—H3 | 109.1 | C9A—C9—C8 | 114.36 (11) |
C9A—C3A—H3 | 109.1 | C9A—C9—H5A | 108.7 |
C3—C3A—H3 | 109.1 | C8—C9—H5A | 108.7 |
C5—C4—C3A | 116.79 (11) | C9A—C9—H5B | 108.7 |
C5—C4—H10A | 108.1 | C8—C9—H5B | 108.7 |
C3A—C4—H10A | 108.1 | H5A—C9—H5B | 107.6 |
C5—C4—H10B | 108.1 | O1—C9A—C9 | 107.20 (10) |
C3A—C4—H10B | 108.1 | O1—C9A—C3A | 103.65 (10) |
H10A—C4—H10B | 107.3 | C9—C9A—C3A | 119.08 (11) |
O3—C5—C4 | 119.65 (12) | O1—C9A—H4 | 108.8 |
O3—C5—C6 | 119.27 (12) | C9—C9A—H4 | 108.8 |
C4—C5—C6 | 121.08 (11) | C3A—C9A—H4 | 108.8 |
C5—C6—C7 | 111.11 (11) | O4—C10—O5 | 124.24 (13) |
C5—C6—H8A | 109.4 | O4—C10—C3 | 124.92 (12) |
C7—C6—H8A | 109.4 | O5—C10—C3 | 110.82 (11) |
C5—C6—H8B | 109.4 | C2—O1—C9A | 110.61 (10) |
C7—C6—H8B | 109.4 | C10—O5—H5 | 109.5 |
H8A—C6—H8B | 108 | ||
O2—C2—C3—C10 | 41.29 (19) | C7—C8—C9—C9A | 98.00 (15) |
O1—C2—C3—C10 | −140.41 (11) | C8—C9—C9A—O1 | 162.10 (11) |
O2—C2—C3—C3A | 164.60 (13) | C8—C9—C9A—C3A | −80.84 (15) |
O1—C2—C3—C3A | −17.11 (14) | C4—C3A—C9A—O1 | −154.82 (10) |
C10—C3—C3A—C4 | −83.43 (13) | C3—C3A—C9A—O1 | −32.98 (12) |
C2—C3—C3A—C4 | 153.96 (11) | C4—C3A—C9A—C9 | 86.28 (14) |
C10—C3—C3A—C9A | 152.78 (11) | C3—C3A—C9A—C9 | −151.87 (11) |
C2—C3—C3A—C9A | 30.16 (12) | C2—C3—C10—O4 | 24.40 (19) |
C9A—C3A—C4—C5 | −62.51 (16) | C3A—C3—C10—O4 | −92.64 (16) |
C3—C3A—C4—C5 | −178.20 (11) | C2—C3—C10—O5 | −157.24 (11) |
C3A—C4—C5—O3 | 150.56 (12) | C3A—C3—C10—O5 | 85.72 (13) |
C3A—C4—C5—C6 | −29.34 (18) | O2—C2—O1—C9A | 173.95 (12) |
O3—C5—C6—C7 | −68.98 (16) | C3—C2—O1—C9A | −4.47 (14) |
C4—C5—C6—C7 | 110.92 (13) | C9—C9A—O1—C2 | 151.11 (11) |
C5—C6—C7—C8 | −48.88 (16) | C3A—C9A—O1—C2 | 24.33 (13) |
C6—C7—C8—C9 | −53.38 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O3i | 0.84 | 1.81 | 2.6292 (13) | 164 |
Symmetry code: (i) −x, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C11H14O5 |
Mr | 226.22 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 123 |
a, b, c (Å) | 8.0792 (1), 10.6879 (2), 24.5704 (5) |
V (Å3) | 2121.65 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.24 × 0.14 × 0.04 |
Data collection | |
Diffractometer | KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23956, 2630, 1847 |
Rint | ? |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.095, 1.06 |
No. of reflections | 2630 |
No. of parameters | 146 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.22 |
Computer programs: COLLECT (Nonius, 1997-2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL SCALEPACK and DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O3i | 0.84 | 1.81 | 2.6292 (13) | 163.6 |
Symmetry code: (i) −x, y−1/2, −z+1/2. |
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The anti stereochemistry of the fused ring systems of the title compound, (I), has been established. The molecular structure of (I) is shown in Fig. 1. A hydrogen-bonded chain structure is formed through an intermolecular hydrogen bond between the carboxylic acid group and the ketone O atom of an adjacent molecule.