In the title compound, the aromatic ring of the 4-hexyloxybenzoyl moiety and the central benzoate ring are twisted relative to one another, subtending a dihedral angle of 39.7 (2)°. The hexyloxy chain adopts an extended, approximately all-anti conformation and two short intramolecular C—H⋯O contacts are observed. In the extended structure, C—H⋯π interactions help to consolidate the packing.
Keywords: crystal structure, Hirshfeld surface, 4-hexyloxy, 4-benzoyloxybenzolate
Abstract
In the title compound, C27H28O5, the aromatic ring of the 4-hexyloxybenzoyl moiety and the central benzoate ring are twisted relative to one another, subtending a dihedral angle of 39.7 (2)°. The pendant benzyl aromatic ring is nearly orthogonal to the central benzoate ring, forming a dihedral angle of 89.3 (2)°. The hexyloxy chain adopts an extended, approximately all-anti conformation and two short intramolecular C—H⋯O contacts are observed. In the extended structure, C—H⋯π interactions help to consolidate the packing. Hirshfeld surface analysis and the corresponding two-dimensional fingerprint plots indicate that H⋯H contacts constitute the largest contribution to the crystal surface, accounting for 55.4%, followed by C⋯H/H⋯C contacts (22.9%) and O⋯H/H⋯O contacts (16.3%).
1. Chemical context
Derivatives of 4-hydroxybenzoic acid have been associated with antimicrobial, antioxidant and anti-inflammatory properties, while naturally occurring alkoxy-substituted benzoic acid derivatives can inhibit inflammatory responses (Manuja et al., 2013 ▸; Chen et al., 2008 ▸). Esterification can modify lipophilicity, membrane transport and susceptibility to enzymatic hydrolysis; accordingly, several alkyl and aryl benzoates have been investigated as antimycobacterial prodrugs (Pais et al., 2022 ▸). Benzyl and other aromatic ester derivatives have also been examined for antimicrobial and antioxidant activities, demonstrating that the nature of the aromatic substituent and ester group can influence biological behavior (Matin et al., 2016 ▸; Kumar et al., 2015 ▸). In materials chemistry, phenyl-benzoate systems containing multiple aromatic rings, ester linkages and flexible terminal alkoxy chains represent an established design for calamitic liquid crystals. Studies of related homologous series show that the length of the terminal alkoxy chain, molecular rigidity and terminal substituents strongly affect melting behaviour and the formation and stability of nematic or smectic phases (Patel & Chauhan, 2016 ▸; Jagtap & Chauhan, 2016 ▸; Balkanli et al., 2021 ▸; Alamro et al., 2024 ▸). Aromatic esters are additionally of interest because their molecular symmetry, rotational freedom and π-stacking tendencies, which influence crystallization and thermal properties (Ravotti et al., 2020 ▸). As part of our studies in this area, we now describe the synthesis and structure of the title compound, C27H25O5 (I).
2. Structural commentary
Compound (I) crystallizes in space group P
, with one molecule in the asymmetric unit (Fig. 1 ▸). The conformation is governed principally by the relative orientations of the three aromatic rings and the intervening ester linkages. The benzyl phenyl ring (C1–C6) is almost perpendicular to the central benzoate ring (C9–C14), forming a dihedral angle of 89.26 (2)°. The 4-hexyloxybenzoyl ring (C16–C21) is inclined to the central ring by 39.70 (12)°, while it forms a dihedral angle of 74.50 (5)° with the benzyl phenyl ring. The molecule therefore adopts a markedly non-coplanar overall conformation. The C—C bond associated with the benzyl ester linkage adopts a near-anti arrangement, as indicated by the C1—C7—O1—C8 torsion angle of −164.86 (14)°. The ester linkage connecting the central and 4-hexyloxybenzoyl fragments is more extended, with a C12—O3—C15—C16 torsion angle of −178.07 (14)°. The carbonyl plane associated with C15 is inclined by 7.85 (13)° to the 4-hexyloxybenzoyl ring but by 33.20 (12)° to the central aromatic ring, showing that conjugation is maintained preferentially on the benzoyl side of the ester group. The hexyloxy substituent also adopts an extended orientation relative to its attached aromatic ring, with a C19—O5—C22—C23 torsion angle of 177.28 (15)°. The subsequent alkyl-chain torsion angles C22—C23—C24—C25 and C23—C24—C25—C26 are 179.98 (17) and −174.58 (18)°, respectively, confirming an approximately all-anti chain conformation. C10—H10⋯O1 and C11—H11⋯O4 intramolecular short contacts (Table 1 ▸) may help to consolidate the molecular conformation.
Figure 1.
The molecular structure of (I) drawn with 50% probability ellipsoids with intramolecular hydrogen bonds and short contacts shown as green and orange dashed lines.
Table 1. Hydrogen-bond geometry (Å, °).
Cg1 and Cg3 represent the centroids of the C1–C6 and C16–C21 aromatic rings, respectively.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C10—H10⋯O1 | 0.93 | 2.41 | 2.730 (2) | 100 |
| C11—H11⋯O4 | 0.93 | 2.40 | 2.851 (2) | 109 |
| C7—H7B⋯Cg1i | 0.97 | 2.92 | 3.602 (2) | 128 |
| C22—H22B⋯Cg3ii | 0.97 | 2.99 | 3.810 (2) | 143 |
| C27—H27A⋯Cg1iii | 0.96 | 2.98 | 3.791 (3) | 143 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
.
3. Supramolecular features
In the extended structure of (I), the packing is reinforced by three C—H⋯π contacts involving C7—H7B⋯Cg1, C22—H22B⋯Cg3 and C27—H27A⋯Cg1, where Cg1 and Cg3 represent the centroids of the C1–C6 and C16–C21 aromatic rings, respectively (Fig. 2 ▸ and Table 1 ▸).
Figure 2.
The packing of (I) with C—H⋯π interactions shown as blue dotted lines.
4. Hirshfeld surface analysis
A Hirshfeld surface analysis was carried out for (I) using Crystal Explorer 17.5 (Spackman et al., 2021 ▸) to further quantify the intermolecular interactions listed in Table 1 ▸. The three-dimensional Hirshfeld surfaces plotted over dnorm and shape-index are shown in Fig. 3 ▸. The red spots around the aromatic rings of the molecule signifies the presence of centroids in Fig. (3b). The two-dimensional fingerprint plots (Fig. 4 ▸) indicate that the most prominent contributions for the Hirshfeld surfaces are from H⋯H (55.4%), C⋯H/H⋯C (22.9%), O⋯H/H⋯O (16.3%) contacts with C⋯C (2.8%), and O⋯C/C⋯O (2.7%) being less significant.
Figure 3.
The Hirshfeld surface view of the title molecule plotted over (a) dnorm and (b) shape index.
Figure 4.
The two-dimensional fingerprint plots for (I) showing H⋯H (55.4%), C⋯H/H⋯C (22.9%), O⋯H/H⋯O (16.3%), C⋯C(2.8%), and O⋯C/C⋯O(2.7%) contacts.
A crystal void analysis was performed using a 0.002 a.u. electron-density isosurface. The calculated void volume (Fig. 5 ▸) and surface area are 143.5 Å3 and 482.5 Å2, respectively. Relative to the unit-cell volume of 1169.3 (7) Å3, the voids occupy approximately 12.3% of the unit cell, indicating a modest amount of unoccupied space within the crystal structure. The relatively high surface-area-to-volume ratio suggests that the void regions have an irregular and extended boundary rather than a compact spherical shape. Interaction energies (Fig. 6 ▸) for (I) using the basis set B3LYP\631-G(d,p) for molecular pairs within the cluster of 3.8 Å radius, gave Eele = −49.7, Epol = −19.5, Edis = −293.4 and Erep = 117 kJ mol−1.
Figure 5.
The crystal voids in (I) viewed along the a, b and c axes.
Figure 6.
The energy framework topology of (I) generated for (a) Coulomb interaction energy, (b) dispersion interaction energy and (c) total interaction energy.
5. Database survey
A search of the Cambridge Structural Database (CSD version 6.01, March 2026; Groom et al., 2016 ▸) for structures containing the 4-hexyloxybenzoate fragment returned six entries, of which three were selected as close matches: CSD refcodes GIKBOT01 (Kuz’mina et al., 2013 ▸), JITNAB (Haase et al., 1991 ▸) and ZIFLOP (Iki & Hori, 1995 ▸). A broader search based on related benzoate and aromatic-ester fragments identified MESQAG (Brown et al., 2021 ▸) and UBAJOZ (Tabuchi et al., 2016 ▸). The dihedral angles between the ester-linked aromatic rings in GIKBOT01, JITNAB and ZIFLOP are 56.4, 66.2 and 1.0°, respectively, showing substantial variation from nearly coplanar to strongly twisted conformations. In contrast, the carbonyl group remains close to the plane of the 4-hexyloxybenzoate ring, with corresponding interplanar angles of 5.6, 7.4 and 0.9°. The C(ar)—O—C—C torsion angles of 166.0, 176.4 and 179.2° indicate predominantly extended hexyloxy chains. In MESQAG, the ester-linked aromatic rings subtend a dihedral angle of 25.4°, while UBAJOZ, a lower pentyloxy homologue, has a carboxyl-group inclination of 2.0° and a C(ar)—O—C—C torsion angle of 168.6°. In (I), the 4-hexyloxybenzoate and central benzoate rings form a dihedral angle of 39.7°, within the range observed for the closest database structures. Thus, the title molecule combines an intermediate twist across the diaryl ester linkage with an almost orthogonal benzyl group and an extended terminal alkoxy chain.
6. Synthesis and crystallization
A mixture of 4-(hexyloxy)benzoic acid (0.223 g, 1 eq), benzyl 4-hydroxybenzoate (0.228 g, 1.0 eq) in dry dichloromethane with dicyclohexylcarbodiimide (DCC) (0.210 g, 1.2 eq) and a catalytic amount of dimethylaminopyrimidine (DMAP) were stirred at room temperature for 6 hrs. The side product N,N-dicyclohexyl urea formed was filtered off and the filtrate diluted with dichloromethane (25ml). This solution was washed successively with 5% aqueous acetic acid solution (2 × 25ml) and water (2 × 25ml) and dried over sodium sulfate. The residue obtained after solvent removal was chromatographed on silica gel using chloroform as eluent. Removal of solvent from the eluate afforded a white material, which was recrystallized from chloroform solution. Yield: 0.145g (75%); elemental analysis calculated: C, 74.98; H, 6.53; O, 18.50% found is C, 75.02; H, 6.55%. 1H NMR (ppm, CDCl3): 8.13 (m, 4H, Ar-H), 7.62 (m, 2H, Ar-H), 7.32 (s, 5H, Ar-H), 7.07 (m, 2H, Ar-H), 5.2 (s, 2H, Ar-CH2–), 4.01 (t, 2H, J = 6.5Hz, –OCH2–), 1.72–1.26 (m, 8H, alkyl-H), 0.92 (t, 3H, J = 4.5Hz, –CH3).
7. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. All hydrogen atoms were positioned with idealized geometry and refined using a riding model with C—H = 0.93–0.97 Å and Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(methyl C).
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C27H28O5 |
| M r | 432.49 |
| Crystal system, space group | Triclinic, P
|
| Temperature (K) | 258 |
| a, b, c (Å) | 5.435 (2), 14.445 (5), 15.277 (5) |
| α, β, γ (°) | 95.104 (11), 95.693 (12), 99.725 (12) |
| V (Å3) | 1169.3 (7) |
| Z | 2 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.08 |
| Crystal size (mm) | 0.38 × 0.32 × 0.27 |
| Data collection | |
| Diffractometer | Bruker SMART APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Krause et al., 2015 ▸) |
| Tmin, Tmax | 0.965, 0.975 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 30609, 6801, 4287 |
| R int | 0.041 |
| (sin θ/λ)max (Å−1) | 0.705 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.155, 1.03 |
| No. of reflections | 6801 |
| No. of parameters | 289 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.17, −0.19 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989026008728/hb8247sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989026008728/hb8247Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989026008728/hb8247Isup3.cml
CCDC reference: 2582616
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank iSTEM and IISc for their help with the single-crystal data collection. PR thanks CISEE and the BSPM lab for extending their help in carry out experiments and for usage of software facilities to complete the research work at University College of Science, Tumkur University, Tumkur.
supplementary crystallographic information
Benzyl 4-{[4-(hexyloxy)benzoyl]oxy}benzoate. Crystal data
| C27H28O5 | Z = 2 |
| Mr = 432.49 | F(000) = 460 |
| Triclinic, P1 | Dx = 1.228 Mg m−3 |
| a = 5.435 (2) Å | Mo Kα radiation, λ = 0.71075 Å |
| b = 14.445 (5) Å | Cell parameters from 4287 reflections |
| c = 15.277 (5) Å | θ = 3.0–30.0° |
| α = 95.104 (11)° | µ = 0.08 mm−1 |
| β = 95.693 (12)° | T = 258 K |
| γ = 99.725 (12)° | PRISM, colourless |
| V = 1169.3 (7) Å3 | 0.38 × 0.32 × 0.27 mm |
Benzyl 4-{[4-(hexyloxy)benzoyl]oxy}benzoate. Data collection
| Bruker SMART APEXII CCD diffractometer | 6801 independent reflections |
| Radiation source: fine-focus sealed tube | 4287 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.041 |
| Detector resolution: 1.09 pixels mm-1 | θmax = 30.1°, θmin = 2.9° |
| φ and Ω scans | h = −7→7 |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −20→18 |
| Tmin = 0.965, Tmax = 0.975 | l = −21→21 |
| 30609 measured reflections |
Benzyl 4-{[4-(hexyloxy)benzoyl]oxy}benzoate. Refinement
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.155 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0557P)2 + 0.2511P] where P = (Fo2 + 2Fc2)/3 |
| 6801 reflections | (Δ/σ)max < 0.001 |
| 289 parameters | Δρmax = 0.17 e Å−3 |
| 0 restraints | Δρmin = −0.19 e Å−3 |
| 0 constraints |
Benzyl 4-{[4-(hexyloxy)benzoyl]oxy}benzoate. 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. |
Benzyl 4-{[4-(hexyloxy)benzoyl]oxy}benzoate. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O1 | 1.6426 (2) | 0.07235 (8) | 0.81958 (7) | 0.0607 (3) | |
| O3 | 0.8144 (2) | 0.18094 (9) | 0.54784 (8) | 0.0666 (3) | |
| O2 | 1.4848 (3) | −0.07220 (9) | 0.75109 (9) | 0.0782 (4) | |
| O5 | 0.0280 (2) | 0.33927 (9) | 0.30299 (8) | 0.0678 (3) | |
| O4 | 0.8199 (3) | 0.31815 (10) | 0.63289 (8) | 0.0808 (4) | |
| C1 | 1.9292 (3) | 0.10443 (11) | 0.95172 (10) | 0.0493 (4) | |
| C9 | 1.3131 (3) | 0.05972 (11) | 0.70564 (9) | 0.0499 (4) | |
| C20 | 0.3129 (4) | 0.24706 (12) | 0.35407 (11) | 0.0612 (4) | |
| H20 | 0.269039 | 0.208193 | 0.300996 | 0.073* | |
| C2 | 1.7985 (3) | 0.11428 (12) | 1.02367 (12) | 0.0610 (4) | |
| H2 | 1.643292 | 0.075687 | 1.024035 | 0.073* | |
| C4 | 2.1198 (4) | 0.23668 (13) | 1.09631 (12) | 0.0664 (5) | |
| H4 | 2.182960 | 0.281542 | 1.144260 | 0.080* | |
| C21 | 0.4898 (3) | 0.22655 (11) | 0.41635 (11) | 0.0589 (4) | |
| H21 | 0.564236 | 0.173890 | 0.405440 | 0.071* | |
| C8 | 1.4860 (3) | 0.01142 (11) | 0.75952 (10) | 0.0521 (4) | |
| C16 | 0.5581 (3) | 0.28465 (11) | 0.49609 (10) | 0.0539 (4) | |
| C6 | 2.1602 (3) | 0.16175 (14) | 0.95446 (13) | 0.0660 (5) | |
| H6 | 2.254073 | 0.156401 | 0.907165 | 0.079* | |
| C14 | 1.1074 (3) | 0.00556 (12) | 0.65275 (11) | 0.0601 (4) | |
| H14 | 1.081061 | −0.059951 | 0.650674 | 0.072* | |
| C3 | 1.8927 (4) | 0.18019 (13) | 1.09529 (12) | 0.0667 (5) | |
| H3 | 1.800466 | 0.185913 | 1.142980 | 0.080* | |
| C7 | 1.8234 (3) | 0.03205 (12) | 0.87481 (11) | 0.0604 (4) | |
| H7A | 1.956701 | 0.017121 | 0.841247 | 0.073* | |
| H7B | 1.741047 | −0.025514 | 0.895508 | 0.073* | |
| C13 | 0.9418 (3) | 0.04852 (12) | 0.60325 (11) | 0.0617 (4) | |
| H13 | 0.802861 | 0.012147 | 0.568504 | 0.074* | |
| C10 | 1.3506 (3) | 0.15727 (12) | 0.70739 (11) | 0.0590 (4) | |
| H10 | 1.487719 | 0.193853 | 0.742930 | 0.071* | |
| C17 | 0.4428 (4) | 0.36262 (12) | 0.51056 (11) | 0.0622 (4) | |
| H17 | 0.487715 | 0.401884 | 0.563367 | 0.075* | |
| C12 | 0.9833 (3) | 0.14575 (12) | 0.60549 (10) | 0.0554 (4) | |
| C11 | 1.1885 (3) | 0.20093 (12) | 0.65745 (12) | 0.0645 (5) | |
| H11 | 1.216235 | 0.266361 | 0.658564 | 0.077* | |
| C23 | −0.2579 (3) | 0.42209 (13) | 0.22933 (12) | 0.0635 (4) | |
| H23A | −0.390594 | 0.366954 | 0.221911 | 0.076* | |
| H23B | −0.161995 | 0.418689 | 0.179229 | 0.076* | |
| C19 | 0.1984 (3) | 0.32520 (11) | 0.36921 (10) | 0.0555 (4) | |
| C25 | −0.5466 (4) | 0.51750 (13) | 0.14900 (13) | 0.0674 (5) | |
| H25A | −0.690556 | 0.466653 | 0.143773 | 0.081* | |
| H25B | −0.458686 | 0.508887 | 0.097466 | 0.081* | |
| C18 | 0.2636 (4) | 0.38315 (12) | 0.44854 (11) | 0.0616 (4) | |
| H18 | 0.187212 | 0.435259 | 0.459687 | 0.074* | |
| C22 | −0.0893 (3) | 0.42082 (13) | 0.31261 (12) | 0.0631 (4) | |
| H22A | 0.037523 | 0.477795 | 0.322945 | 0.076* | |
| H22B | −0.186202 | 0.418017 | 0.362624 | 0.076* | |
| C15 | 0.7438 (3) | 0.26666 (13) | 0.56663 (11) | 0.0590 (4) | |
| C5 | 2.2540 (4) | 0.22708 (15) | 1.02661 (15) | 0.0764 (5) | |
| H5 | 2.410880 | 0.264954 | 1.027520 | 0.092* | |
| C24 | −0.3743 (4) | 0.51068 (14) | 0.23047 (13) | 0.0691 (5) | |
| H24A | −0.467955 | 0.513670 | 0.281196 | 0.083* | |
| H24B | −0.239926 | 0.565277 | 0.238672 | 0.083* | |
| C26 | −0.6385 (5) | 0.61033 (15) | 0.14930 (16) | 0.0867 (6) | |
| H26A | −0.715063 | 0.620716 | 0.203206 | 0.104* | |
| H26B | −0.494380 | 0.660514 | 0.150885 | 0.104* | |
| C27 | −0.8227 (5) | 0.6180 (2) | 0.0728 (2) | 0.1078 (8) | |
| H27A | −0.870148 | 0.679130 | 0.078621 | 0.162* | |
| H27B | −0.747822 | 0.609865 | 0.018914 | 0.162* | |
| H27C | −0.968994 | 0.569979 | 0.071350 | 0.162* |
Benzyl 4-{[4-(hexyloxy)benzoyl]oxy}benzoate. Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0742 (8) | 0.0520 (6) | 0.0519 (6) | 0.0168 (6) | −0.0136 (6) | −0.0034 (5) |
| O3 | 0.0830 (8) | 0.0635 (7) | 0.0500 (6) | 0.0195 (6) | −0.0134 (6) | −0.0004 (5) |
| O2 | 0.1054 (11) | 0.0520 (7) | 0.0711 (8) | 0.0231 (7) | −0.0184 (7) | −0.0113 (6) |
| O5 | 0.0801 (8) | 0.0648 (7) | 0.0565 (7) | 0.0263 (6) | −0.0129 (6) | −0.0064 (6) |
| O4 | 0.0916 (10) | 0.0900 (9) | 0.0540 (7) | 0.0273 (8) | −0.0178 (7) | −0.0204 (7) |
| C1 | 0.0526 (9) | 0.0504 (8) | 0.0467 (8) | 0.0198 (7) | −0.0020 (7) | 0.0033 (6) |
| C9 | 0.0602 (9) | 0.0507 (8) | 0.0364 (7) | 0.0064 (7) | 0.0052 (6) | −0.0009 (6) |
| C20 | 0.0793 (12) | 0.0528 (9) | 0.0469 (8) | 0.0146 (8) | −0.0085 (8) | −0.0076 (7) |
| C2 | 0.0545 (9) | 0.0623 (10) | 0.0634 (10) | 0.0058 (8) | 0.0093 (8) | −0.0027 (8) |
| C4 | 0.0731 (12) | 0.0608 (10) | 0.0593 (10) | 0.0150 (9) | −0.0165 (9) | −0.0048 (8) |
| C21 | 0.0764 (11) | 0.0501 (9) | 0.0485 (9) | 0.0166 (8) | −0.0030 (8) | −0.0031 (7) |
| C8 | 0.0636 (10) | 0.0527 (9) | 0.0391 (7) | 0.0118 (7) | 0.0060 (7) | −0.0027 (6) |
| C16 | 0.0625 (10) | 0.0521 (9) | 0.0444 (8) | 0.0076 (7) | 0.0016 (7) | 0.0012 (7) |
| C6 | 0.0596 (11) | 0.0764 (12) | 0.0638 (11) | 0.0145 (9) | 0.0134 (9) | 0.0064 (9) |
| C14 | 0.0741 (11) | 0.0469 (8) | 0.0538 (9) | 0.0071 (8) | −0.0030 (8) | −0.0051 (7) |
| C3 | 0.0790 (13) | 0.0689 (11) | 0.0525 (9) | 0.0179 (10) | 0.0101 (9) | −0.0026 (8) |
| C7 | 0.0696 (11) | 0.0597 (10) | 0.0530 (9) | 0.0255 (8) | −0.0050 (8) | −0.0020 (7) |
| C13 | 0.0677 (11) | 0.0580 (10) | 0.0519 (9) | 0.0069 (8) | −0.0092 (8) | −0.0089 (7) |
| C10 | 0.0654 (10) | 0.0520 (9) | 0.0523 (9) | −0.0001 (8) | −0.0085 (8) | 0.0035 (7) |
| C17 | 0.0805 (12) | 0.0595 (10) | 0.0437 (8) | 0.0146 (9) | 0.0008 (8) | −0.0081 (7) |
| C12 | 0.0654 (10) | 0.0596 (9) | 0.0394 (8) | 0.0112 (8) | −0.0008 (7) | 0.0027 (7) |
| C11 | 0.0722 (11) | 0.0503 (9) | 0.0649 (11) | 0.0009 (8) | −0.0074 (9) | 0.0092 (8) |
| C23 | 0.0639 (11) | 0.0638 (10) | 0.0619 (10) | 0.0167 (9) | −0.0007 (8) | 0.0004 (8) |
| C19 | 0.0631 (10) | 0.0533 (9) | 0.0476 (8) | 0.0096 (8) | −0.0013 (7) | 0.0019 (7) |
| C25 | 0.0647 (11) | 0.0639 (11) | 0.0734 (12) | 0.0187 (9) | 0.0002 (9) | 0.0018 (9) |
| C18 | 0.0756 (11) | 0.0576 (9) | 0.0521 (9) | 0.0214 (9) | 0.0031 (8) | −0.0045 (7) |
| C22 | 0.0651 (11) | 0.0633 (10) | 0.0612 (10) | 0.0189 (9) | 0.0018 (8) | 0.0005 (8) |
| C15 | 0.0650 (10) | 0.0636 (10) | 0.0461 (9) | 0.0111 (8) | 0.0001 (8) | 0.0007 (7) |
| C5 | 0.0547 (10) | 0.0754 (13) | 0.0907 (15) | −0.0011 (9) | −0.0021 (10) | 0.0000 (11) |
| C24 | 0.0730 (12) | 0.0699 (11) | 0.0655 (11) | 0.0236 (10) | 0.0027 (9) | −0.0020 (9) |
| C26 | 0.1012 (16) | 0.0715 (13) | 0.0904 (15) | 0.0324 (12) | 0.0009 (13) | 0.0043 (11) |
| C27 | 0.1066 (19) | 0.1006 (18) | 0.126 (2) | 0.0428 (15) | 0.0030 (16) | 0.0336 (16) |
Benzyl 4-{[4-(hexyloxy)benzoyl]oxy}benzoate. Geometric parameters (Å, º)
| O1—C8 | 1.3377 (19) | C7—H7A | 0.9700 |
| O1—C7 | 1.4603 (19) | C7—H7B | 0.9700 |
| O3—C15 | 1.372 (2) | C13—C12 | 1.381 (2) |
| O3—C12 | 1.398 (2) | C13—H13 | 0.9300 |
| O2—C8 | 1.2022 (19) | C10—C11 | 1.377 (2) |
| O5—C19 | 1.355 (2) | C10—H10 | 0.9300 |
| O5—C22 | 1.434 (2) | C17—C18 | 1.378 (2) |
| O4—O4 | 0.0000 (1) | C17—H17 | 0.9300 |
| O4—C15 | 1.195 (2) | C12—C11 | 1.386 (2) |
| C1—C2 | 1.376 (2) | C11—H11 | 0.9300 |
| C1—C6 | 1.377 (2) | C23—C22 | 1.496 (2) |
| C1—C7 | 1.499 (2) | C23—C24 | 1.520 (2) |
| C9—C10 | 1.387 (2) | C23—H23A | 0.9700 |
| C9—C14 | 1.388 (2) | C23—H23B | 0.9700 |
| C9—C8 | 1.489 (2) | C19—C18 | 1.389 (2) |
| C20—C21 | 1.372 (2) | C25—C24 | 1.503 (3) |
| C20—C19 | 1.391 (2) | C25—C26 | 1.508 (3) |
| C20—H20 | 0.9300 | C25—H25A | 0.9700 |
| C2—C3 | 1.380 (2) | C25—H25B | 0.9700 |
| C2—H2 | 0.9300 | C18—H18 | 0.9300 |
| C4—C3 | 1.357 (3) | C22—H22A | 0.9700 |
| C4—C5 | 1.359 (3) | C22—H22B | 0.9700 |
| C4—H4 | 0.9300 | C5—H5 | 0.9300 |
| C21—C16 | 1.396 (2) | C24—H24A | 0.9700 |
| C21—H21 | 0.9300 | C24—H24B | 0.9700 |
| C16—C17 | 1.390 (2) | C26—C27 | 1.486 (3) |
| C16—C15 | 1.473 (2) | C26—H26A | 0.9700 |
| C6—C5 | 1.381 (3) | C26—H26B | 0.9700 |
| C6—H6 | 0.9300 | C27—H27A | 0.9600 |
| C14—C13 | 1.380 (2) | C27—H27B | 0.9600 |
| C14—H14 | 0.9300 | C27—H27C | 0.9600 |
| C3—H3 | 0.9300 | ||
| C8—O1—C7 | 116.02 (12) | C10—C11—C12 | 118.91 (16) |
| C15—O3—C12 | 122.50 (13) | C10—C11—H11 | 120.5 |
| C19—O5—C22 | 118.92 (13) | C12—C11—H11 | 120.5 |
| C2—C1—C6 | 117.47 (15) | C22—C23—C24 | 111.89 (15) |
| C2—C1—C7 | 120.48 (16) | C22—C23—H23A | 109.2 |
| C6—C1—C7 | 122.03 (16) | C24—C23—H23A | 109.2 |
| C10—C9—C14 | 119.11 (15) | C22—C23—H23B | 109.2 |
| C10—C9—C8 | 121.85 (14) | C24—C23—H23B | 109.2 |
| C14—C9—C8 | 119.04 (14) | H23A—C23—H23B | 107.9 |
| C21—C20—C19 | 120.91 (15) | O5—C19—C18 | 124.48 (15) |
| C21—C20—H20 | 119.5 | O5—C19—C20 | 115.99 (14) |
| C19—C20—H20 | 119.5 | C18—C19—C20 | 119.53 (15) |
| C1—C2—C3 | 121.44 (17) | C24—C25—C26 | 113.46 (17) |
| C1—C2—H2 | 119.3 | C24—C25—H25A | 108.9 |
| C3—C2—H2 | 119.3 | C26—C25—H25A | 108.9 |
| C3—C4—C5 | 119.39 (17) | C24—C25—H25B | 108.9 |
| C3—C4—H4 | 120.3 | C26—C25—H25B | 108.9 |
| C5—C4—H4 | 120.3 | H25A—C25—H25B | 107.7 |
| C20—C21—C16 | 120.07 (15) | C17—C18—C19 | 119.30 (16) |
| C20—C21—H21 | 120.0 | C17—C18—H18 | 120.4 |
| C16—C21—H21 | 120.0 | C19—C18—H18 | 120.4 |
| O2—C8—O1 | 123.68 (15) | O5—C22—C23 | 108.17 (14) |
| O2—C8—C9 | 124.53 (15) | O5—C22—H22A | 110.1 |
| O1—C8—C9 | 111.79 (13) | C23—C22—H22A | 110.1 |
| C17—C16—C21 | 118.60 (15) | O5—C22—H22B | 110.1 |
| C17—C16—C15 | 118.11 (14) | C23—C22—H22B | 110.1 |
| C21—C16—C15 | 123.29 (15) | H22A—C22—H22B | 108.4 |
| C1—C6—C5 | 120.76 (18) | O4—C15—O3 | 123.77 (16) |
| C1—C6—H6 | 119.6 | O4—C15—O3 | 123.77 (16) |
| C5—C6—H6 | 119.6 | O4—C15—C16 | 125.12 (17) |
| C13—C14—C9 | 120.27 (15) | O4—C15—C16 | 125.12 (17) |
| C13—C14—H14 | 119.9 | O3—C15—C16 | 111.09 (14) |
| C9—C14—H14 | 119.9 | C4—C5—C6 | 120.76 (18) |
| C4—C3—C2 | 120.17 (18) | C4—C5—H5 | 119.6 |
| C4—C3—H3 | 119.9 | C6—C5—H5 | 119.6 |
| C2—C3—H3 | 119.9 | C25—C24—C23 | 115.27 (16) |
| O1—C7—C1 | 107.28 (12) | C25—C24—H24A | 108.5 |
| O1—C7—H7A | 110.3 | C23—C24—H24A | 108.5 |
| C1—C7—H7A | 110.3 | C25—C24—H24B | 108.5 |
| O1—C7—H7B | 110.3 | C23—C24—H24B | 108.5 |
| C1—C7—H7B | 110.3 | H24A—C24—H24B | 107.5 |
| H7A—C7—H7B | 108.5 | C27—C26—C25 | 115.4 (2) |
| C14—C13—C12 | 119.74 (16) | C27—C26—H26A | 108.4 |
| C14—C13—H13 | 120.1 | C25—C26—H26A | 108.4 |
| C12—C13—H13 | 120.1 | C27—C26—H26B | 108.4 |
| C11—C10—C9 | 121.17 (16) | C25—C26—H26B | 108.4 |
| C11—C10—H10 | 119.4 | H26A—C26—H26B | 107.5 |
| C9—C10—H10 | 119.4 | C26—C27—H27A | 109.5 |
| C18—C17—C16 | 121.59 (15) | C26—C27—H27B | 109.5 |
| C18—C17—H17 | 119.2 | H27A—C27—H27B | 109.5 |
| C16—C17—H17 | 119.2 | C26—C27—H27C | 109.5 |
| C13—C12—C11 | 120.79 (16) | H27A—C27—H27C | 109.5 |
| C13—C12—O3 | 114.70 (14) | H27B—C27—H27C | 109.5 |
| C11—C12—O3 | 124.38 (15) | ||
| C6—C1—C2—C3 | 1.1 (3) | C9—C10—C11—C12 | 0.7 (3) |
| C7—C1—C2—C3 | 179.76 (16) | C13—C12—C11—C10 | −0.3 (3) |
| C19—C20—C21—C16 | −0.3 (3) | O3—C12—C11—C10 | −175.85 (16) |
| C7—O1—C8—O2 | 1.7 (2) | C22—O5—C19—C18 | 2.2 (3) |
| C7—O1—C8—C9 | −178.90 (13) | C22—O5—C19—C20 | −177.34 (16) |
| C10—C9—C8—O2 | −168.55 (17) | C21—C20—C19—O5 | 179.47 (16) |
| C14—C9—C8—O2 | 12.0 (2) | C21—C20—C19—C18 | −0.1 (3) |
| C10—C9—C8—O1 | 12.1 (2) | C16—C17—C18—C19 | −0.7 (3) |
| C14—C9—C8—O1 | −167.38 (14) | O5—C19—C18—C17 | −178.92 (17) |
| C20—C21—C16—C17 | 0.2 (3) | C20—C19—C18—C17 | 0.6 (3) |
| C20—C21—C16—C15 | 179.18 (17) | C19—O5—C22—C23 | 177.28 (15) |
| C2—C1—C6—C5 | −0.7 (3) | C24—C23—C22—O5 | −175.30 (16) |
| C7—C1—C6—C5 | −179.28 (17) | O4—O4—C15—O3 | 0.0 (4) |
| C10—C9—C14—C13 | −0.5 (3) | O4—O4—C15—C16 | 0.0 (5) |
| C8—C9—C14—C13 | 178.95 (15) | C12—O3—C15—O4 | 0.2 (3) |
| C5—C4—C3—C2 | −0.6 (3) | C12—O3—C15—O4 | 0.2 (3) |
| C1—C2—C3—C4 | −0.5 (3) | C12—O3—C15—C16 | −178.07 (14) |
| C8—O1—C7—C1 | −164.86 (14) | C17—C16—C15—O4 | −6.6 (3) |
| C2—C1—C7—O1 | 81.28 (19) | C21—C16—C15—O4 | 174.47 (19) |
| C6—C1—C7—O1 | −100.15 (18) | C17—C16—C15—O4 | −6.6 (3) |
| C9—C14—C13—C12 | 0.9 (3) | C21—C16—C15—O4 | 174.47 (19) |
| C14—C9—C10—C11 | −0.3 (3) | C17—C16—C15—O3 | 171.62 (15) |
| C8—C9—C10—C11 | −179.74 (16) | C21—C16—C15—O3 | −7.3 (2) |
| C21—C16—C17—C18 | 0.3 (3) | C3—C4—C5—C6 | 1.1 (3) |
| C15—C16—C17—C18 | −178.71 (17) | C1—C6—C5—C4 | −0.4 (3) |
| C14—C13—C12—C11 | −0.5 (3) | C26—C25—C24—C23 | −174.58 (18) |
| C14—C13—C12—O3 | 175.46 (15) | C22—C23—C24—C25 | 179.98 (17) |
| C15—O3—C12—C13 | 148.39 (16) | C24—C25—C26—C27 | −176.2 (2) |
| C15—O3—C12—C11 | −35.8 (3) |
Benzyl 4-{[4-(hexyloxy)benzoyl]oxy}benzoate. Hydrogen-bond geometry (Å, º)
Cg1 and Cg3 represent the centroids of the C1–C6 and C16–C21 aromatic rings, respectively.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C10—H10···O1 | 0.93 | 2.41 | 2.730 (2) | 100 |
| C11—H11···O4 | 0.93 | 2.40 | 2.851 (2) | 109 |
| C7—H7B···Cg1i | 0.97 | 2.92 | 3.602 (2) | 128 |
| C22—H22B···Cg3ii | 0.97 | 2.99 | 3.810 (2) | 143 |
| C27—H27A···Cg1iii | 0.96 | 2.98 | 3.791 (3) | 143 |
Symmetry codes: (i) −x+4, −y, −z+2; (ii) x−1, y, z; (iii) −x+1, −y+1, −z+1.
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/S2056989026008728/hb8247sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989026008728/hb8247Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989026008728/hb8247Isup3.cml
CCDC reference: 2582616
Additional supporting information: crystallographic information; 3D view; checkCIF report