Download citation
Download citation
link to html
The stereochemistry about the lactone ring system of the title compound, C19H16O5, has been established. Intermolecular hydrogen bonds are observed between carboxyl­ic acid groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001617/tk6052sup1.cif
Contains datablocks k52_01, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001617/tk6052Isup2.hkl
Contains datablock I

CCDC reference: 182626

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.096
  • Data-to-parameter ratio = 17.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

To establish the stereochemistry about the lactone ring system of (±)-ethyl 2-oxo-4-(2-oxp-2-phenylethyl)-5-phenyltetrahydrofuran-3-carboxylate (Greatrex et al., 2002), the structure of the derived acid, (I), was determined. The molecular structure of (I) is shown in Fig. 1. A centrosymmetric dimer is formed through a strong intermolecular hydrogen bond between centrosymmetrically related carboxylic acid groups (Table 1).

Experimental top

The title compound was prepared by base-catalyzed hydrolysis of the parent ethyl ester, as previously described (Greatrex et al., 2002). Crystals suitable for X-ray analysis were grown by slow evaporation from a CH2Cl2/hexane (1:1) solution of the compound.

Refinement top

The H atoms were included in the riding-model approximation.

Computing details top

Data collection: COLLECT (Nonius BV, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; 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).

Figures top
[Figure 1] Fig. 1. View of (I) (50% probability displacement ellipsoids).
(I) top
Crystal data top
C19H16O5Dx = 1.364 Mg m3
Mr = 324.32Melting point = 130–132 K
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 30.0282 (4) ÅCell parameters from 20303 reflections
b = 8.9226 (1) Åθ = 3.4–28.3°
c = 12.1979 (2) ŵ = 0.10 mm1
β = 104.884 (1)°T = 123 K
V = 3158.52 (8) Å3Prismatic, colourless
Z = 80.27 × 0.13 × 0.1 mm
F(000) = 1360
Data collection top
Nonius KappaCCD
diffractometer
Rint = 0.037
CCD–rotation images, thick slices scansθmax = 28.3°, θmin = 3.4°
21591 measured reflectionsh = 4040
3871 independent reflectionsk = 1111
3023 reflections with I > 2σ(I)l = 1615
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.045 w = 1/[σ2(Fo2) + (0.033P)2 + 2.4814P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.25 e Å3
3871 reflectionsΔρmin = 0.21 e Å3
218 parameters
Crystal data top
C19H16O5V = 3158.52 (8) Å3
Mr = 324.32Z = 8
Monoclinic, C2/cMo Kα radiation
a = 30.0282 (4) ŵ = 0.10 mm1
b = 8.9226 (1) ÅT = 123 K
c = 12.1979 (2) Å0.27 × 0.13 × 0.1 mm
β = 104.884 (1)°
Data collection top
Nonius KappaCCD
diffractometer
3023 reflections with I > 2σ(I)
21591 measured reflectionsRint = 0.037
3871 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.25 e Å3
3871 reflectionsΔρmin = 0.21 e Å3
218 parameters
Special details top

Experimental. m.p. 130–132°C decomp.

IR(nujol) 1783, 1711, 1678, 1457, 1377, 1336, 1300, 1267 cm-1.

1H n.m.r. (300 MHz, CDCl3): δ 2.67 (dd,J=9.3, 18.6 Hz, 1H), 3.26 (dd,J=5.1, 18.6 Hz, 1H), 3.64 (d,J=10.8 Hz, 1H), 3.90, (dddd,J=5.1, 7.8, 9.3, 10.8 Hz, 1H), 6.14 (d,J=7.8 Hz, 1H), 7.12–7.14 (m,2H), 7.31–7.36 (m,3H), 7.42–7.44 (m,2H), 7.51–7.57 (m,1H), 7.74–7.77 (m,2H).

MS (M+,%) 324 (M.+, 12), 280 (10), 252 (18), 174 (15), 146 (28), 120 (25), 105 (100), 77 (52).

Anal. Calcd. for C19H16O5: C, 70.36; H, 4.97%. Found C, 70.31; H, 4.90%.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O20.02622 (3)0.06044 (11)0.61898 (8)0.0237 (2)
O30.05222 (3)0.43059 (11)0.51859 (9)0.0310 (3)
O10.09404 (3)0.00993 (10)0.59291 (7)0.0211 (2)
O50.19441 (3)0.20465 (11)0.45237 (8)0.0264 (2)
O40.01351 (3)0.31388 (11)0.43670 (10)0.0364 (3)
H40.02510.39520.45030.055*
C6'0.18191 (4)0.32455 (14)0.27511 (11)0.0192 (3)
C70.12161 (5)0.09861 (15)0.43314 (11)0.0223 (3)
C8'0.16888 (5)0.42504 (16)0.08592 (12)0.0259 (3)
H8'0.14960.43750.01150.031*
C20.05491 (5)0.07121 (14)0.56675 (11)0.0196 (3)
C30.05476 (4)0.17228 (14)0.46548 (11)0.0185 (3)
H30.03770.1210.39410.022*
C60.03137 (4)0.31961 (15)0.47628 (11)0.0204 (3)
C40.10582 (4)0.18119 (14)0.46827 (11)0.0184 (3)
H4a0.12020.25940.52510.022*
C5'0.16628 (5)0.24622 (14)0.36648 (11)0.0197 (3)
C50.12375 (5)0.02611 (15)0.51819 (11)0.0203 (3)
H50.15620.0370.5650.024*
C120.08136 (5)0.17789 (16)0.38821 (11)0.0257 (3)
H120.05440.15590.41230.031*
C4'0.11532 (4)0.22346 (15)0.35525 (11)0.0192 (3)
H4'10.10360.14320.29920.023*
H4'20.09850.31690.32670.023*
C100.11918 (7)0.32168 (18)0.27205 (13)0.0385 (4)
H100.11820.3970.21640.046*
C11'0.22634 (5)0.38428 (16)0.30194 (12)0.0237 (3)
H11'0.24630.36830.37520.028*
C80.16096 (6)0.13375 (17)0.39779 (14)0.0318 (4)
H80.18890.08170.42920.038*
C9'0.21256 (5)0.48722 (17)0.11422 (12)0.0289 (3)
H9'0.22290.54410.05970.035*
C7'0.15318 (5)0.34436 (15)0.16621 (11)0.0219 (3)
H7'0.1230.30290.1470.026*
C90.15950 (6)0.24448 (18)0.31686 (14)0.0398 (4)
H90.18630.2670.29240.048*
C10'0.24141 (5)0.46674 (17)0.22220 (12)0.0282 (3)
H10'0.27140.50920.24130.034*
C110.08033 (6)0.28965 (17)0.30798 (13)0.0339 (4)
H110.05270.34410.27790.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0238 (5)0.0242 (5)0.0270 (5)0.0034 (4)0.0138 (4)0.0045 (4)
O30.0198 (5)0.0178 (5)0.0540 (7)0.0015 (4)0.0070 (5)0.0065 (5)
O10.0231 (5)0.0205 (5)0.0231 (5)0.0037 (4)0.0118 (4)0.0025 (4)
O50.0204 (5)0.0321 (6)0.0260 (5)0.0007 (4)0.0047 (4)0.0068 (4)
O40.0182 (5)0.0223 (6)0.0654 (8)0.0037 (4)0.0045 (5)0.0123 (5)
C6'0.0201 (7)0.0163 (6)0.0236 (7)0.0026 (5)0.0099 (5)0.0004 (5)
C70.0282 (8)0.0173 (7)0.0246 (7)0.0080 (5)0.0128 (6)0.0063 (5)
C8'0.0326 (8)0.0251 (7)0.0217 (7)0.0045 (6)0.0100 (6)0.0013 (6)
C20.0206 (7)0.0155 (6)0.0233 (7)0.0009 (5)0.0071 (5)0.0044 (5)
C30.0174 (7)0.0158 (6)0.0238 (7)0.0001 (5)0.0079 (5)0.0003 (5)
C60.0191 (7)0.0191 (7)0.0255 (7)0.0011 (5)0.0100 (5)0.0026 (5)
C40.0178 (6)0.0155 (6)0.0232 (7)0.0013 (5)0.0079 (5)0.0009 (5)
C5'0.0207 (7)0.0159 (6)0.0235 (7)0.0010 (5)0.0074 (5)0.0009 (5)
C50.0193 (7)0.0215 (7)0.0229 (7)0.0039 (5)0.0102 (5)0.0039 (5)
C120.0301 (8)0.0220 (7)0.0255 (7)0.0082 (6)0.0082 (6)0.0013 (6)
C4'0.0187 (7)0.0176 (6)0.0222 (7)0.0010 (5)0.0072 (5)0.0019 (5)
C100.0689 (12)0.0233 (8)0.0283 (8)0.0163 (8)0.0218 (8)0.0034 (6)
C11'0.0206 (7)0.0254 (7)0.0265 (7)0.0018 (6)0.0089 (6)0.0014 (6)
C80.0367 (9)0.0226 (7)0.0443 (9)0.0075 (6)0.0253 (7)0.0065 (6)
C9'0.0342 (8)0.0273 (8)0.0313 (8)0.0029 (6)0.0198 (7)0.0072 (6)
C7'0.0233 (7)0.0191 (7)0.0247 (7)0.0014 (5)0.0085 (6)0.0026 (5)
C90.0574 (12)0.0270 (8)0.0485 (10)0.0171 (8)0.0382 (9)0.0085 (7)
C10'0.0234 (7)0.0283 (8)0.0364 (8)0.0015 (6)0.0138 (6)0.0033 (6)
C110.0478 (10)0.0234 (8)0.0278 (8)0.0077 (7)0.0050 (7)0.0005 (6)
Geometric parameters (Å, º) top
O2—C21.1996 (16)C4—C51.5514 (18)
O3—C61.2137 (16)C4—H4a1
O1—C21.3470 (16)C5'—C4'1.5143 (18)
O1—C51.4653 (15)C5—H51
O5—C5'1.2224 (16)C12—C111.392 (2)
O4—C61.3106 (16)C12—H120.95
O4—H40.84C4'—H4'10.99
C6'—C11'1.3953 (19)C4'—H4'20.99
C6'—C7'1.3970 (18)C10—C111.377 (2)
C6'—C5'1.4900 (18)C10—C91.378 (3)
C7—C121.386 (2)C10—H100.95
C7—C81.3934 (19)C11'—C10'1.3850 (19)
C7—C51.5115 (19)C11'—H11'0.95
C8'—C9'1.384 (2)C8—C91.389 (2)
C8'—C7'1.3917 (19)C8—H80.95
C8'—H8'0.95C9'—C10'1.390 (2)
C2—C31.5285 (18)C9'—H9'0.95
C3—C61.5120 (18)C7'—H7'0.95
C3—C41.5269 (17)C9—H90.95
C3—H31C10'—H10'0.95
C4—C4'1.5252 (18)C11—H110.95
C2—O1—C5111.60 (10)C7—C5—H5109.1
C6—O4—H4109.5C4—C5—H5109.1
C11'—C6'—C7'119.64 (12)C7—C12—C11120.20 (14)
C11'—C6'—C5'118.02 (12)C7—C12—H12119.9
C7'—C6'—C5'122.30 (12)C11—C12—H12119.9
C12—C7—C8119.04 (13)C5'—C4'—C4111.76 (10)
C12—C7—C5121.73 (12)C5'—C4'—H4'1109.3
C8—C7—C5119.23 (13)C4—C4'—H4'1109.3
C9'—C8'—C7'120.17 (13)C5'—C4'—H4'2109.3
C9'—C8'—H8'119.9C4—C4'—H4'2109.3
C7'—C8'—H8'119.9H4'1—C4'—H4'2107.9
O2—C2—O1122.21 (12)C11—C10—C9119.97 (15)
O2—C2—C3128.53 (12)C11—C10—H10120
O1—C2—C3109.26 (10)C9—C10—H10120
C6—C3—C4116.04 (11)C10'—C11'—C6'120.22 (13)
C6—C3—C2110.34 (10)C10'—C11'—H11'119.9
C4—C3—C2102.61 (10)C6'—C11'—H11'119.9
C6—C3—H3109.2C9—C8—C7120.36 (16)
C4—C3—H3109.2C9—C8—H8119.8
C2—C3—H3109.2C7—C8—H8119.8
O3—C6—O4123.91 (12)C8'—C9'—C10'120.25 (13)
O3—C6—C3123.09 (12)C8'—C9'—H9'119.9
O4—C6—C3113.00 (11)C10'—C9'—H9'119.9
C4'—C4—C3114.38 (11)C8'—C7'—C6'119.77 (13)
C4'—C4—C5116.66 (10)C8'—C7'—H7'120.1
C3—C4—C5101.98 (10)C6'—C7'—H7'120.1
C4'—C4—H4a107.8C10—C9—C8120.09 (15)
C3—C4—H4a107.8C10—C9—H9120
C5—C4—H4a107.8C8—C9—H9120
O5—C5'—C6'120.15 (12)C11'—C10'—C9'119.91 (13)
O5—C5'—C4'119.78 (12)C11'—C10'—H10'120
C6'—C5'—C4'120.03 (11)C9'—C10'—H10'120
O1—C5—C7109.89 (11)C10—C11—C12120.32 (16)
O1—C5—C4103.57 (10)C10—C11—H11119.8
C7—C5—C4115.97 (11)C12—C11—H11119.8
O1—C5—H5109.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O3i0.841.842.6782 (14)178
Symmetry code: (i) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC19H16O5
Mr324.32
Crystal system, space groupMonoclinic, C2/c
Temperature (K)123
a, b, c (Å)30.0282 (4), 8.9226 (1), 12.1979 (2)
β (°) 104.884 (1)
V3)3158.52 (8)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.27 × 0.13 × 0.1
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
21591, 3871, 3023
Rint0.037
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.096, 1.03
No. of reflections3871
No. of parameters218
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.21

Computer programs: COLLECT (Nonius BV, 1997-2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O3i0.841.842.6782 (14)178
Symmetry code: (i) x, y+1, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds