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. 2025 Jan 7;10(Pt 1):x241241. doi: 10.1107/S2414314624012410

Tetra­phenyl­glycolide tetra­hydro­furan monosolvate

Lubabalo Ndima a, Eric Cyriel Hosten a, Richard Betz a,*
Editor: R J Butcherb
PMCID: PMC11799779  PMID: 39927306

The title compound is the symmetric glycolide derived from benzilic acid featuring a disordered tetra­hydro­furan solvent mol­ecule in the crystal structure.

Keywords: crystal structure, glycolide, C—H⋯O contacts

Abstract

The title compound, C28H20O4·C4H4O, is the cyclic ester anhydride of benzilic acid. A disordered solvent mol­ecule is present in the structure. The asymmetric unit contains half the acid-derived mol­ecule. C—H⋯O contacts connect the constituents of the title compound into a three-dimensional network.graphic file with name x-10-x241241-scheme1-3D1.jpg

Structure description

Heterocyclic compounds play a major role in biological systems, with sugars and the building blocks of DNA even being part of many high school curricula (Stryer, 1988 ▸). Owing to this finding, pharmaceutical research often employs aromatic and alicyclic compounds as leitmotifs from which potentially powerful new drugs can be derived. Against this backdrop it is not surprising that structural information about this class of mol­ecules, although already abundant, still constitutes a considerable focus of research up to this day. As part of our ongoing studies in this area (Nayak et al., 2014 ▸; Mohamed et al., 2023 ▸; Dayananda et al., 2013 ▸; Lulama & Betz, 2015 ▸; Betz & Klüfers, 2007a ▸,b ▸,c ▸, 2008 ▸, 2009 ▸; Betz et al., 2008 ▸, 2011 ▸, 2009 ▸, 2010 ▸; Potgieter et al., 2011 ▸; Hosten & Betz, 2014 ▸; Averdunk et al., 2021a ▸,b ▸), we sought to determine the crystal structure of the title compound that was obtained as a surprising outcome of an inorganic non-metal compound reaction. The crystal and mol­ecular structure of the solvent-free equivalent of the title compound are apparent in the literature (Shan et al., 2005 ▸) as are other examples of symmetric cyclic ester anhydrides such as, e.g., the ones derived from glycolic acid (Hutchison et al., 2017 ▸; Belenkaya et al., 1997 ▸), lactic acid (Chisholm et al., 2000 ▸; van Hummel et al., 1982 ▸; Belenkaya et al., 1997 ▸) or 3-chloro­lactic acid (Kalelkar et al., 2016 ▸), as well as examples of asymmetric members of this compound class such as the condensation products of lactic acid and mandelic acid (Nifant’ev et al., 2020 ▸). The lactide of thiol­actic acid represents the only example where the mol­ecular and crystal structure of a thio­nated glycolide has been secured on grounds of diffraction studies on single crystals (Mangalum et al., 2016 ▸).

The title compound is the cyclic ester anhydride of benzilic acid. The structure refinement was conducted as a two-component inversion twin with a volume ratio of 75.1:24.9. The asymmetric unit contains half a mol­ecule. One disordered mol­ecule of tetra­hydro­furan is also present in the crystal structure. The C—O and C=O bond lengths are found at 1.467 (3) and 1.340 (3) Å, respectively, and, therefore, are in good agreement with values reported for other cyclic lactides whose mol­ecular and crystal structures have been determined on grounds of diffraction studies on single crystals and whose metrical parameters have been deposited with the Cambridge Structural Database (Groom et al., 2016 ▸). A conformational analysis of the six-membered heterocycle according to Cremer & Pople (1975 ▸) shows the latter to adopt a confirmation almost exactly in between a 4T2 (O1iTC1) as well as a BC1,C1i conformation (Boeyens, 1978 ▸). The phenyl rings are orientated almost perpendicular to one another as the least-squares planes, as defined by the respective carbon atoms of the aromatic moieties, enclose an angle of 85.34 (16)° (Fig. 1 ▸).

Figure 1.

Figure 1

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The mol­ecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at the 50% probability level). For clarity, the disordered THF mol­ecule has been omitted. Symmetry code: (i) y, x, −z + 1.

In the crystal, there are C—H⋯O contacts (Table 1 ▸) whose range falls by more than 0.1 Å below the sum of the van der Waals radii of the atoms participating in them. These are supported by one hydrogen atom each in the ortho-position on two of the aromatic systems as donors and, invariably, the oxygen atom of the solvent mol­ecule as acceptor. A second type of C—H⋯O contact is found between one hydrogen atom each in meta-position on the remaining two phenyl groups (that had not participated in the previously described contacts) as donors and the two carbonylic oxygen atoms as acceptors. In terms of graph-set analysis (Etter et al., 1990 ▸; Bernstein et al., 1995 ▸), the descriptor for these C—H⋯O contacts requires a DDC11(7) Inline graphic(7) descriptor on the unary level. In total, these inter­actions connect the constituents present in the crystal structure of the title compound to a three-dimensional network. Furthermore, one C—H⋯π contact is apparent between one of the hydrogen atoms in the meta-position on one of the phenyl groups giving rise to the C—H⋯O inter­actions towards the solvent mol­ecule as donor and one of the aromatic systems of an aromatic system that gives rise to the contacts involving the carbonyl group. In addition, the structure is further consolidated by π-stacking inter­actions with the shortest distance between two centres of gravity measured at 3.8915 (19) Å in between two phenyl groups, giving rise to the C—H⋯O contacts towards the solvent mol­ecule present in the crystal structure (Fig. 2 ▸).

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of carbon atoms C21–C26.

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C12—H12⋯O2i 0.95 2.55 3.185 (4) 124
C15—H15⋯O2ii 0.95 2.57 3.494 (4) 166
C26—H26⋯O3 0.95 2.17 3.060 (7) 155
C13—H13⋯Cg1iii 0.95 2.90 3.799 (4) 158
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Symmetry codes: (i) Inline graphic; (ii) Inline graphic; (iii) Inline graphic.

Figure 2.

Figure 2

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Inter­molecular contacts, viewed approximately along [110].

Synthesis and crystallization

The compound was obtained by reacting penta­carbonyl­rhenium(I) chloride and the hydrido­spiro­phospho­rane derived from benzilic acid in the mixed solvents of THF/benzene/di­ethyl­ether. Crystals suitable for the diffraction study were obtained upon concentrating the reaction mixture and subsequent storage at room temperature.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The modelling of the disordered THF mol­ecule was conducted applying RIGU and ISOR instructions.

Table 2. Experimental details.

Crystal data
Chemical formula C28H20O4·C4H4O
M r 488.51
Crystal system, space group Tetragonal, P43212
Temperature (K) 200
a, c (Å) 9.5725 (3), 27.5760 (11)
V (Å3) 2526.86 (18)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.09
Crystal size (mm) 0.24 × 0.23 × 0.15
 
Data collection
Diffractometer Bruker D8 Quest CCD
Absorption correction Multi-scan (SADABS; Krause et al., 2015 ▸)
Tmin, Tmax 0.717, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 62563, 2796, 2460
R int 0.080
(sin θ/λ)max (Å−1) 0.641
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.176, 1.09
No. of reflections 2796
No. of parameters 182
No. of restraints 60
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.61, −0.49
Absolute structure Refined as an inversion twin
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Computer programs: APEX2 and SAINT (Bruker, 2014 ▸), SHELXS97 (Sheldrick 2008 ▸), SHELXL2019/3 (Sheldrick, 2015 ▸), ORTEP-3 for Windows (Farrugia, 2012 ▸), Mercury (Macrae et al., 2020 ▸) and PLATON (Spek, 2020 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2414314624012410/bv4054sup1.cif

x-10-x241241-sup1.cif (1.8MB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314624012410/bv4054Isup2.hkl

x-10-x241241-Isup2.hkl (224KB, hkl)
x-10-x241241-Isup3.cml (9.6KB, cml)

Supporting information file. DOI: 10.1107/S2414314624012410/bv4054Isup3.cml

CCDC reference: 2412616

Additional supporting information: crystallographic information; 3D view; checkCIF report

full crystallographic data

3,3,6,6-Tetraphenyl-1,4-dioxane-2,5-dione tetrahydrofuran monosolvate. Crystal data

C28H20O4·C4H4O Dx = 1.284 Mg m−3
Mr = 488.51 Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43212 Cell parameters from 9736 reflections
a = 9.5725 (3) Å θ = 2.3–27.2°
c = 27.5760 (11) Å µ = 0.09 mm−1
V = 2526.86 (18) Å3 T = 200 K
Z = 4 Block, colourless
F(000) = 1024 0.24 × 0.23 × 0.15 mm
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3,3,6,6-Tetraphenyl-1,4-dioxane-2,5-dione tetrahydrofuran monosolvate. Data collection

Bruker D8 Quest CCD diffractometer 2460 reflections with I > 2σ(I)
φ and ω scans Rint = 0.080
Absorption correction: multi-scan (SADABS; Krause et al., 2015) θmax = 27.1°, θmin = 2.3°
Tmin = 0.717, Tmax = 0.746 h = −12→11
62563 measured reflections k = −12→11
2796 independent reflections l = −34→35
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3,3,6,6-Tetraphenyl-1,4-dioxane-2,5-dione tetrahydrofuran monosolvate. Refinement

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)] = 0.056 H-atom parameters constrained
wR(F2) = 0.176 w = 1/[σ2(Fo2) + (0.1205P)2 + 0.5364P] where P = (Fo2 + 2Fc2)/3
S = 1.09 (Δ/σ)max < 0.001
2796 reflections Δρmax = 0.61 e Å−3
182 parameters Δρmin = −0.49 e Å−3
60 restraints Absolute structure: Refined as an inversion twin
Primary atom site location: structure-invariant direct methods Absolute structure parameter: 0 (2)
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3,3,6,6-Tetraphenyl-1,4-dioxane-2,5-dione tetrahydrofuran monosolvate. Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refined as a 2-component inversion twin. The carbon-bound H atoms were placed in calculated positions (C–H 0.95 Å for aromatic carbon atoms and methylene groups) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).
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3,3,6,6-Tetraphenyl-1,4-dioxane-2,5-dione tetrahydrofuran monosolvate. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)
O1 0.4588 (2) 0.4898 (2) 0.54864 (6) 0.0319 (5)
O2 0.2991 (2) 0.6508 (2) 0.53907 (7) 0.0368 (5)
C1 0.5915 (3) 0.4283 (3) 0.53272 (9) 0.0283 (6)
C2 0.3893 (3) 0.5818 (3) 0.52110 (9) 0.0260 (5)
C11 0.7086 (3) 0.5314 (3) 0.54213 (9) 0.0298 (6)
C12 0.8216 (3) 0.5456 (3) 0.51104 (11) 0.0379 (7)
H12 0.825856 0.490886 0.482324 0.046*
C13 0.9293 (4) 0.6394 (4) 0.52150 (13) 0.0492 (8)
H13 1.006380 0.648771 0.500032 0.059*
C14 0.9226 (4) 0.7188 (4) 0.56365 (14) 0.0538 (9)
H14 0.995517 0.782443 0.571219 0.065*
C15 0.8095 (4) 0.7051 (4) 0.59457 (12) 0.0505 (9)
H15 0.804601 0.760230 0.623176 0.061*
C16 0.7043 (4) 0.6123 (3) 0.58411 (11) 0.0401 (7)
H16 0.627644 0.603108 0.605757 0.048*
C21 0.6034 (3) 0.2930 (3) 0.56191 (9) 0.0310 (6)
C22 0.7258 (3) 0.2549 (3) 0.58459 (10) 0.0392 (7)
H22 0.805731 0.313339 0.582405 0.047*
C23 0.7323 (4) 0.1301 (4) 0.61081 (12) 0.0503 (9)
H23 0.816855 0.103912 0.626369 0.060*
C24 0.6182 (4) 0.0460 (4) 0.61418 (12) 0.0511 (9)
H24 0.623033 −0.038158 0.632355 0.061*
C25 0.4949 (4) 0.0829 (4) 0.59113 (14) 0.0516 (9)
H25 0.415367 0.023889 0.593483 0.062*
C26 0.4876 (4) 0.2054 (4) 0.56472 (13) 0.0444 (8)
H26 0.403565 0.229794 0.548486 0.053*
O3 0.2067 (8) 0.1892 (10) 0.5120 (3) 0.095 (3) 0.5
C31 0.2086 (7) 0.0816 (11) 0.4766 (3) 0.127 (6) 0.5
H31 0.289498 0.042872 0.461821 0.153* 0.5
C32 0.0683 (8) 0.0420 (8) 0.4671 (3) 0.091 (3) 0.5
H32 0.038849 −0.027875 0.444817 0.109* 0.5
C33 −0.0203 (6) 0.1251 (9) 0.4966 (3) 0.082 (3) 0.5
H33 −0.119378 0.120617 0.497626 0.099* 0.5
C34 0.0653 (9) 0.2161 (8) 0.5244 (3) 0.097 (4) 0.5
H34 0.033481 0.283137 0.547268 0.116* 0.5
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3,3,6,6-Tetraphenyl-1,4-dioxane-2,5-dione tetrahydrofuran monosolvate. Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0334 (10) 0.0385 (11) 0.0238 (8) 0.0097 (8) 0.0075 (7) 0.0069 (8)
O2 0.0376 (11) 0.0416 (11) 0.0311 (10) 0.0111 (9) 0.0033 (8) −0.0019 (9)
C1 0.0287 (13) 0.0338 (13) 0.0223 (12) 0.0089 (11) 0.0041 (10) 0.0025 (10)
C2 0.0259 (12) 0.0266 (12) 0.0255 (12) −0.0022 (10) 0.0001 (9) −0.0012 (9)
C11 0.0360 (14) 0.0294 (12) 0.0241 (12) 0.0061 (11) −0.0051 (11) 0.0009 (10)
C12 0.0380 (16) 0.0394 (16) 0.0364 (15) −0.0027 (12) 0.0019 (12) −0.0064 (12)
C13 0.0434 (18) 0.051 (2) 0.0529 (19) −0.0079 (16) −0.0027 (15) −0.0047 (15)
C14 0.061 (2) 0.0406 (17) 0.060 (2) −0.0069 (17) −0.0195 (18) −0.0056 (16)
C15 0.073 (3) 0.0374 (16) 0.0415 (16) 0.0089 (16) −0.0189 (16) −0.0097 (14)
C16 0.0496 (18) 0.0400 (16) 0.0306 (14) 0.0108 (14) −0.0041 (13) −0.0054 (12)
C21 0.0364 (15) 0.0320 (13) 0.0247 (12) 0.0053 (11) 0.0049 (10) 0.0039 (10)
C22 0.0412 (16) 0.0417 (16) 0.0349 (14) 0.0062 (14) −0.0043 (12) 0.0082 (12)
C23 0.063 (2) 0.0485 (19) 0.0395 (16) 0.0148 (18) −0.0063 (16) 0.0110 (14)
C24 0.073 (3) 0.0398 (17) 0.0403 (16) 0.0146 (17) 0.0148 (17) 0.0148 (14)
C25 0.051 (2) 0.0387 (17) 0.065 (2) 0.0018 (16) 0.0213 (17) 0.0127 (16)
C26 0.0357 (16) 0.0423 (17) 0.0551 (19) 0.0058 (13) 0.0056 (14) 0.0129 (15)
O3 0.059 (3) 0.113 (5) 0.113 (6) 0.001 (3) −0.009 (4) −0.019 (4)
C31 0.110 (7) 0.118 (8) 0.154 (8) 0.011 (5) 0.026 (6) −0.027 (6)
C32 0.090 (5) 0.091 (5) 0.092 (5) 0.014 (4) −0.010 (4) −0.028 (4)
C33 0.070 (4) 0.102 (5) 0.074 (5) 0.021 (4) −0.008 (4) −0.015 (4)
C34 0.066 (5) 0.092 (6) 0.132 (7) 0.001 (4) 0.017 (5) −0.024 (5)
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3,3,6,6-Tetraphenyl-1,4-dioxane-2,5-dione tetrahydrofuran monosolvate. Geometric parameters (Å, º)

O1—C2 1.340 (3) C22—C23 1.398 (4)
O1—C1 1.467 (3) C22—H22 0.9500
O2—C2 1.195 (3) C23—C24 1.360 (6)
C1—C11 1.516 (4) C23—H23 0.9500
C1—C21 1.529 (4) C24—C25 1.386 (6)
C1—C2i 1.533 (3) C24—H24 0.9500
C11—C12 1.387 (4) C25—C26 1.382 (5)
C11—C16 1.393 (4) C25—H25 0.9500
C12—C13 1.397 (5) C26—H26 0.9500
C12—H12 0.9500 O3—C31 1.4200
C13—C14 1.391 (5) O3—C34 1.4200
C13—H13 0.9500 C31—C32 1.4200
C14—C15 1.384 (6) C31—H31 0.9500
C14—H14 0.9500 C32—C33 1.4200
C15—C16 1.374 (5) C32—H32 0.9500
C15—H15 0.9500 C33—C34 1.4200
C16—H16 0.9500 C33—H33 0.9500
C21—C22 1.377 (4) C34—H34 0.9500
C21—C26 1.392 (5)
C2—O1—C1 121.62 (19) C26—C21—C1 118.7 (3)
O1—C1—C11 109.1 (2) C21—C22—C23 119.9 (3)
O1—C1—C21 104.3 (2) C21—C22—H22 120.0
C11—C1—C21 114.0 (2) C23—C22—H22 120.0
O1—C1—C2i 109.6 (2) C24—C23—C22 120.4 (3)
C11—C1—C2i 111.6 (2) C24—C23—H23 119.8
C21—C1—C2i 107.9 (2) C22—C23—H23 119.8
O2—C2—O1 119.2 (2) C23—C24—C25 120.1 (3)
O2—C2—C1i 122.9 (2) C23—C24—H24 119.9
O1—C2—C1i 117.9 (2) C25—C24—H24 119.9
C12—C11—C16 118.9 (3) C26—C25—C24 120.0 (4)
C12—C11—C1 122.3 (2) C26—C25—H25 120.0
C16—C11—C1 118.8 (3) C24—C25—H25 120.0
C11—C12—C13 120.7 (3) C25—C26—C21 120.0 (3)
C11—C12—H12 119.6 C25—C26—H26 120.0
C13—C12—H12 119.6 C21—C26—H26 120.0
C14—C13—C12 119.3 (3) C31—O3—C34 108.0
C14—C13—H13 120.3 O3—C31—C32 108.0
C12—C13—H13 120.3 O3—C31—H31 126.0
C15—C14—C13 120.0 (3) C32—C31—H31 126.0
C15—C14—H14 120.0 C31—C32—C33 108.0
C13—C14—H14 120.0 C31—C32—H32 126.0
C16—C15—C14 120.3 (3) C33—C32—H32 126.0
C16—C15—H15 119.8 C34—C33—C32 108.0
C14—C15—H15 119.8 C34—C33—H33 126.0
C15—C16—C11 120.8 (3) C32—C33—H33 126.0
C15—C16—H16 119.6 C33—C34—O3 108.0
C11—C16—H16 119.6 C33—C34—H34 126.0
C22—C21—C26 119.5 (3) O3—C34—H34 126.0
C22—C21—C1 121.8 (3)
C2—O1—C1—C11 80.3 (3) O1—C1—C21—C22 −134.4 (3)
C2—O1—C1—C21 −157.5 (2) C11—C1—C21—C22 −15.5 (4)
C2—O1—C1—C2i −42.2 (3) C2i—C1—C21—C22 109.1 (3)
C1—O1—C2—O2 −164.4 (3) O1—C1—C21—C26 46.7 (3)
C1—O1—C2—C1i 16.7 (3) C11—C1—C21—C26 165.6 (3)
O1—C1—C11—C12 −144.0 (3) C2i—C1—C21—C26 −69.8 (3)
C21—C1—C11—C12 99.9 (3) C26—C21—C22—C23 −1.0 (5)
C2i—C1—C11—C12 −22.7 (4) C1—C21—C22—C23 −179.8 (3)
O1—C1—C11—C16 37.7 (3) C21—C22—C23—C24 −0.1 (5)
C21—C1—C11—C16 −78.5 (3) C22—C23—C24—C25 0.7 (5)
C2i—C1—C11—C16 158.9 (2) C23—C24—C25—C26 −0.1 (5)
C16—C11—C12—C13 −0.1 (5) C24—C25—C26—C21 −1.1 (5)
C1—C11—C12—C13 −178.4 (3) C22—C21—C26—C25 1.6 (5)
C11—C12—C13—C14 0.1 (5) C1—C21—C26—C25 −179.5 (3)
C12—C13—C14—C15 −0.4 (5) C34—O3—C31—C32 0.0
C13—C14—C15—C16 0.7 (5) O3—C31—C32—C33 0.0
C14—C15—C16—C11 −0.6 (5) C31—C32—C33—C34 0.0
C12—C11—C16—C15 0.3 (4) C32—C33—C34—O3 0.0
C1—C11—C16—C15 178.7 (3) C31—O3—C34—C33 0.0
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Symmetry code: (i) y, x, −z+1.

3,3,6,6-Tetraphenyl-1,4-dioxane-2,5-dione tetrahydrofuran monosolvate. Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of carbon atoms C21–C26.

D—H···A D—H H···A D···A D—H···A
C12—H12···O2i 0.95 2.55 3.185 (4) 124
C15—H15···O2ii 0.95 2.57 3.494 (4) 166
C26—H26···O3 0.95 2.17 3.060 (7) 155
C13—H13···Cg1iii 0.95 2.90 3.799 (4) 158
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Symmetry codes: (i) y, x, −z+1; (ii) x+1/2, −y+3/2, −z+5/4; (iii) x+3/2, −y+1/2, −z+5/4.

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2414314624012410/bv4054sup1.cif

x-10-x241241-sup1.cif (1.8MB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314624012410/bv4054Isup2.hkl

x-10-x241241-Isup2.hkl (224KB, hkl)
x-10-x241241-Isup3.cml (9.6KB, cml)

Supporting information file. DOI: 10.1107/S2414314624012410/bv4054Isup3.cml

CCDC reference: 2412616

Additional supporting information: crystallographic information; 3D view; checkCIF report

Articles from IUCrData are provided here courtesy of International Union of Crystallography

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