The central cyclohexenone ring of the non-planar title compound adopts an envelope conformation. The crystal structure of the compound is stabilized by C—H⋯O and C—H⋯π interactions, forming a three-dimensional network.
Keywords: crystal structure, Michael addition products, cyclohexen-1-one ring, envelope conformation, Hirshfeld surface analysis
Abstract
In the title compound, C25H20O2, the central cyclohexenone ring adopts an envelope conformation. The mean plane of the cyclohexenone ring makes dihedral angles of 87.66 (11) and 23.76 (12)°, respectively, with the two attached phenyl rings, while it is inclined by 69.55 (11)° to the phenyl ring of the benzoyl group. In the crystal, the molecules are linked by C—H⋯O and C—H⋯π interactions, forming a three-dimensional network.
Chemical context
There have been a series of significant examples of enone derivatives used as target products as well as synthetic intermediates (Abdelhamid et al., 2011 ▸; Asgarova et al., 2019 ▸; Khalilov et al., 2018a
▸,b
▸; Thomas, 2007 ▸). Moreover, a number of useful compounds containing enone moieties have been found in nature, such as cyanthiwigin U, (+)-cepharamine, phorbol and grandisine G, which were the object of a total synthesis (Pfeiffer et al., 2005 ▸; Schultz & Wang, 1998 ▸; Kawamura et al., 2016 ▸; Cuthbertson & Taylor, 2013 ▸). As part of a further study on the chemistry of α,β-unsaturated ketones (Naghiyev et al., 2016 ▸), we report herein the crystal structure and Hirshfeld surface analysis of the title compound.
Structural commentary
In the title compound (Fig. 1 ▸), the central cyclohexenone ring adopts an envelope conformation with puckering parameters Q T = 0.470 (2) Å, θ = 125.3 (2)° and φ = 300.8 (3)°. The mean plane of the cyclohexenone ring [maximum deviation = 0.335 (2) Å] makes dihedral angles of 87.66 (11) and 23.76 (12)°, respectively, with the C14–C18 and C20–C25 phenyl rings, whereas it is inclined by 69.55 (11)° to the C8–C13 phenyl ring of the benzoyl group.
Figure 1.
The molecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. H atoms are shown as spheres of arbitrary radius.
Supramolecular features and Hirshfeld surface analysis
In the crystal, the molecules are linked by C—H⋯O and C—H⋯π interactions (C2—H2A⋯O2i, C15—H15A⋯O1i, C22—H22A⋯O1ii and C11—H11A⋯Cg3iii; symmetry codes as given in Table 1 ▸; Cg3 is the centroid of the C14–C19 ring), forming layers parallel to the ab plane. The layers are further connected by another C—H⋯π interaction (C24—H24A⋯Cg2 iv; Table 1 ▸; Cg2 is the centroid of the C8–C13 ring), forming a three-dimensional network (Fig. 2 ▸).
Table 1. Hydrogen-bond geometry (Å, °).
Cg2 and Cg3 are the centroids of the C8–C13 and C14–C19 phenyl rings, respectively.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C2—H2A⋯O2i | 0.98 | 2.50 | 3.251 (3) | 133 |
| C15—H15A⋯O1i | 0.93 | 2.55 | 3.369 (3) | 148 |
| C22—H22A⋯O1ii | 0.93 | 2.54 | 3.472 (3) | 175 |
| C11—H11A⋯Cg3iii | 0.93 | 2.88 | 3.717 (2) | 150 |
| C24—H24A⋯Cg2iv | 0.93 | 2.78 | 3.667 (3) | 159 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
; (iv) 
.
Figure 2.
A packing view of the title compound, formed by C—H⋯O and C—H⋯π interactions (dashed lines). [Symmetry codes: (a) x − 1, y, z; (b) x + 1, y, z; (c) −x + 
, y − 
, −z + ; (d) x − , −y + , z + ; (e) x + , −y + , z − .]
The Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ▸) was performed using CrystalExplorer 3.1 (Wolff et al., 2012 ▸). The surface of the title compound mapped over d norm is shown in Fig. 3 ▸. The dark-red spots on the d norm surface arise as a result of short interatomic contacts, while the other weaker intermolecular interactions appear as light-red spots. The Hirshfeld surface mapped over electrostatic potential (Spackman et al., 2008 ▸; Jayatilaka et al., 2005 ▸) is shown in Fig. 4 ▸. The blue regions indicate positive electrostatic potential (hydrogen-bond donors), while the red regions indicate negative electrostatic potential (hydrogen-bond acceptors). The overall two-dimensional fingerprint plot (Spackman & McKinnon, 2002 ▸), and those delineated into H⋯H (48.8%), C⋯H/H⋯C (34.9%) and O⋯H/H⋯O (15%) contacts are illustrated in Fig. 5 ▸ a–d, respectively. The most significant intermolecular contribution is from the H⋯H contact (48.8%) (Fig. 5 ▸ b). The other minor contributions to the Hirshfeld surface are by C⋯C (0.9%), O⋯C/C⋯O (0.5%) and O⋯O (0.1%) contacts. The large number of H⋯H, C⋯H/H⋯C and O⋯H/H⋯O interactions suggest that van der Waals interactions and hydrogen bonding play the major roles in the crystal packing (Hathwar et al., 2015 ▸).
Figure 3.
The Hirshfeld surface of the title compound plotted over d norm using a standard surface resolution with a fixed colour scale of −0.1582 (red) to 1.4399 a.u. (blue).
Figure 4.
The Hirshfeld surface of the title compound plotted over electrostatic potential energy in the range from −0.0500 to 0.0500 a.u. using the STO-3 G basis set at the Hartree–Fock level of theory. Hydrogen-bond donors and acceptors are shown as blue and red regions around the atoms, corresponding to positive and negative potentials, respectively.
Figure 5.
The two-dimensional fingerprint plots for the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) C⋯H/H⋯C, (d) O⋯H/H⋯O interactions. The d i and d e values are the closest internal and external distances (Å) from given points on the Hirshfeld surface.
Database survey
Although a search of the Cambridge Structural Database (CSD, Version 5.41, November 2019; Groom et al., 2016 ▸) for 3,5-diphenylcyclohex-2-en-1-one derivatives gave 44 hits, no compound having a skeleton of 6-acetyl-3,5-diphenylcyclohex-2-en-1-one was found. As related compounds, nine derivatives of ethyl 2-oxo-4,6-diphenylcyclohex-3-ene carboxylate were reported.
Synthesis and crystallization
To a solution of 1,3-diphenyl-2-propen-1-one (1.90 mmol) in benzene (15 ml), 1-phenylbutane-1,3-dione (1.90 mmol) and 0.05 ml of dry piperidine were added in this order, and the mixture was stirred at room temperature for 24 h. After completion of the reaction (as monitored by TLC), the solvent was removed under reduced pressure, and the residue was washed with hot water. Then, the products were recrystallized from ethanol (yield 72%, m.p. 446 K). IR (KBr): 2926, 2966, 3006 and 3062 ν(CH), 1610, 1650 and 1676 ν (C=O) cm−1; 1H NMR (300.130 MHz, DMSO-d6): δ 3.12 (dd, 2H, CH2, 2 J H–H = 16.3 Hz, 3 J H–H = 8.2 Hz), 3.91 (t, 1H, CH, 3 J H–H = 12.4 Hz), 5.52 (d, 1H, CH, 3 J H–H = 12.4 Hz), 6.56 (s, 1H, CH=), 7.1–7.92 (m, 15Harom, 3Ar); 13C NMR (75.468 MHz, DMSO-d 6): δ 199.4, 197.5, 159.6, 142.7, 138.3, 137.8, 133.7, 130.9, 129.3, 129.1, 128.8, 128.0, 127.2, 126.9, 124.2, 58.2, 43.9, 36.4; MS (ESI): m/z: 353.15 [M + H]+.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. All H atoms were placed at calculated positions using a riding model, with C—H = 0.93–0.98 Å, and with U
iso(H) = 1.2U
eq(C). Owing to poor agreement between observed and calculated intensities, eighteen outliers (
2 5) , (3 2 2) , (
2 2) , (5 0 3) , (0 1 1) , (5 1 3) , (
0 4) , ( 1 7) , (
2 3) , ( 3 5) , ( 11 2) , (2 4 3), (4 8 7) , (
0 7) , ( 10 5) , (2 5 5) , ( 2 15) and (0 1 2) were omitted in the final cycle of refinement.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C25H20O2 |
| M r | 352.41 |
| Crystal system, space group | Monoclinic, P21/n |
| Temperature (K) | 296 |
| a, b, c (Å) | 10.2365 (4), 9.7989 (4), 19.3759 (8) |
| β (°) | 103.333 (2) |
| V (Å3) | 1891.14 (13) |
| Z | 4 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.08 |
| Crystal size (mm) | 0.23 × 0.20 × 0.12 |
| Data collection | |
| Diffractometer | Bruker APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Bruker, 2003 ▸) |
| T min, T max | 0.660, 0.746 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 23764, 4102, 2471 |
| R int | 0.073 |
| (sin θ/λ)max (Å−1) | 0.639 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.059, 0.149, 1.01 |
| No. of reflections | 4102 |
| No. of parameters | 244 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.19, −0.19 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989020005381/is5536sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989020005381/is5536Isup2.hkl
CCDC reference: 1983451
Additional supporting information: crystallographic information; 3D view; checkCIF report
supplementary crystallographic information
Crystal data
| C25H20O2 | F(000) = 744 |
| Mr = 352.41 | Dx = 1.238 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| a = 10.2365 (4) Å | Cell parameters from 3243 reflections |
| b = 9.7989 (4) Å | θ = 2.5–25.0° |
| c = 19.3759 (8) Å | µ = 0.08 mm−1 |
| β = 103.333 (2)° | T = 296 K |
| V = 1891.14 (13) Å3 | Prism, colourless |
| Z = 4 | 0.23 × 0.20 × 0.12 mm |
Data collection
| Bruker APEXII CCD diffractometer | 2471 reflections with I > 2σ(I) |
| φ and ω scans | Rint = 0.073 |
| Absorption correction: multi-scan (SADABS; Bruker, 2003) | θmax = 27.0°, θmin = 2.1° |
| Tmin = 0.660, Tmax = 0.746 | h = −13→13 |
| 23764 measured reflections | k = −12→12 |
| 4102 independent reflections | l = −24→24 |
Refinement
| Refinement on F2 | Primary atom site location: difference Fourier map |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.149 | H-atom parameters constrained |
| S = 1.00 | w = 1/[σ2(Fo2) + (0.0717P)2 + 0.020P] where P = (Fo2 + 2Fc2)/3 |
| 4102 reflections | (Δ/σ)max < 0.001 |
| 244 parameters | Δρmax = 0.19 e Å−3 |
| 0 restraints | Δρmin = −0.19 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.84873 (15) | 0.4571 (2) | 0.84508 (9) | 0.0662 (5) | |
| O2 | 0.73311 (16) | 0.59881 (16) | 0.68577 (9) | 0.0556 (4) | |
| C1 | 0.7327 (2) | 0.4250 (2) | 0.81963 (11) | 0.0432 (5) | |
| C2 | 0.68555 (19) | 0.3941 (2) | 0.74035 (11) | 0.0377 (5) | |
| H2A | 0.703396 | 0.297799 | 0.732533 | 0.045* | |
| C3 | 0.53461 (19) | 0.4203 (2) | 0.71377 (10) | 0.0380 (5) | |
| H3A | 0.519851 | 0.518223 | 0.718969 | 0.046* | |
| C4 | 0.4572 (2) | 0.3451 (3) | 0.76099 (11) | 0.0471 (6) | |
| H4A | 0.362962 | 0.369151 | 0.746260 | 0.056* | |
| H4B | 0.464862 | 0.247638 | 0.754221 | 0.056* | |
| C5 | 0.5064 (2) | 0.3775 (2) | 0.83834 (10) | 0.0388 (5) | |
| C6 | 0.6339 (2) | 0.4151 (2) | 0.86315 (11) | 0.0442 (5) | |
| H6A | 0.661662 | 0.436354 | 0.911083 | 0.053* | |
| C7 | 0.7682 (2) | 0.4818 (2) | 0.70074 (11) | 0.0401 (5) | |
| C8 | 0.89014 (19) | 0.4261 (2) | 0.68142 (11) | 0.0403 (5) | |
| C9 | 0.9499 (2) | 0.5025 (3) | 0.63619 (12) | 0.0532 (6) | |
| H9A | 0.912888 | 0.586024 | 0.619070 | 0.064* | |
| C10 | 1.0629 (2) | 0.4558 (3) | 0.61664 (13) | 0.0612 (7) | |
| H10A | 1.101409 | 0.507482 | 0.586302 | 0.073* | |
| C11 | 1.1189 (2) | 0.3329 (3) | 0.64180 (13) | 0.0580 (7) | |
| H11A | 1.194874 | 0.301126 | 0.628243 | 0.070* | |
| C12 | 1.0623 (2) | 0.2568 (3) | 0.68717 (13) | 0.0570 (6) | |
| H12A | 1.101121 | 0.174324 | 0.704782 | 0.068* | |
| C13 | 0.9480 (2) | 0.3026 (2) | 0.70664 (12) | 0.0486 (6) | |
| H13A | 0.909822 | 0.250122 | 0.736835 | 0.058* | |
| C14 | 0.47921 (18) | 0.3846 (2) | 0.63661 (10) | 0.0375 (5) | |
| C15 | 0.4852 (2) | 0.2530 (3) | 0.61136 (12) | 0.0515 (6) | |
| H15A | 0.529328 | 0.185343 | 0.641574 | 0.062* | |
| C16 | 0.4257 (2) | 0.2214 (3) | 0.54103 (13) | 0.0604 (7) | |
| H16A | 0.429682 | 0.132362 | 0.525007 | 0.073* | |
| C17 | 0.3615 (2) | 0.3190 (3) | 0.49526 (13) | 0.0620 (7) | |
| H17A | 0.322732 | 0.297407 | 0.448269 | 0.074* | |
| C18 | 0.3552 (3) | 0.4496 (3) | 0.51981 (13) | 0.0625 (7) | |
| H18A | 0.311330 | 0.516816 | 0.489171 | 0.075* | |
| C19 | 0.4131 (2) | 0.4825 (2) | 0.58944 (12) | 0.0491 (6) | |
| H19A | 0.407775 | 0.571668 | 0.604998 | 0.059* | |
| C20 | 0.4106 (2) | 0.3634 (2) | 0.88513 (11) | 0.0398 (5) | |
| C21 | 0.2742 (2) | 0.3877 (3) | 0.86040 (13) | 0.0550 (6) | |
| H21A | 0.241528 | 0.412364 | 0.813221 | 0.066* | |
| C22 | 0.1862 (2) | 0.3760 (3) | 0.90421 (15) | 0.0667 (8) | |
| H22A | 0.095277 | 0.393434 | 0.886588 | 0.080* | |
| C23 | 0.2324 (3) | 0.3389 (3) | 0.97356 (15) | 0.0662 (7) | |
| H23A | 0.173169 | 0.331066 | 1.003253 | 0.079* | |
| C24 | 0.3663 (3) | 0.3132 (3) | 0.99904 (14) | 0.0625 (7) | |
| H24A | 0.397718 | 0.287297 | 1.046135 | 0.075* | |
| C25 | 0.4553 (2) | 0.3253 (3) | 0.95566 (12) | 0.0516 (6) | |
| H25A | 0.545976 | 0.307812 | 0.973826 | 0.062* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0359 (9) | 0.1016 (15) | 0.0586 (10) | −0.0170 (9) | 0.0056 (8) | −0.0036 (9) |
| O2 | 0.0606 (10) | 0.0407 (10) | 0.0728 (11) | 0.0030 (8) | 0.0305 (9) | 0.0069 (8) |
| C1 | 0.0342 (11) | 0.0494 (13) | 0.0456 (13) | −0.0024 (10) | 0.0084 (9) | 0.0009 (10) |
| C2 | 0.0310 (10) | 0.0410 (12) | 0.0426 (12) | −0.0015 (9) | 0.0115 (9) | 0.0000 (9) |
| C3 | 0.0340 (10) | 0.0434 (12) | 0.0379 (11) | 0.0018 (9) | 0.0107 (9) | −0.0001 (9) |
| C4 | 0.0342 (11) | 0.0680 (16) | 0.0398 (12) | −0.0073 (10) | 0.0101 (9) | 0.0004 (11) |
| C5 | 0.0367 (11) | 0.0434 (13) | 0.0376 (12) | 0.0024 (9) | 0.0112 (9) | 0.0001 (9) |
| C6 | 0.0398 (12) | 0.0545 (14) | 0.0378 (12) | 0.0003 (10) | 0.0074 (9) | −0.0019 (10) |
| C7 | 0.0383 (11) | 0.0404 (13) | 0.0428 (12) | −0.0034 (10) | 0.0118 (9) | −0.0003 (9) |
| C8 | 0.0354 (11) | 0.0432 (12) | 0.0434 (12) | −0.0054 (9) | 0.0111 (9) | −0.0038 (10) |
| C9 | 0.0485 (13) | 0.0566 (15) | 0.0587 (15) | −0.0081 (11) | 0.0211 (11) | 0.0045 (12) |
| C10 | 0.0459 (14) | 0.0793 (19) | 0.0643 (17) | −0.0090 (13) | 0.0248 (12) | 0.0062 (14) |
| C11 | 0.0313 (11) | 0.082 (2) | 0.0644 (16) | −0.0024 (12) | 0.0176 (11) | −0.0128 (14) |
| C12 | 0.0389 (12) | 0.0618 (16) | 0.0717 (16) | 0.0052 (11) | 0.0159 (12) | 0.0005 (13) |
| C13 | 0.0407 (12) | 0.0528 (15) | 0.0557 (14) | −0.0018 (10) | 0.0183 (10) | 0.0054 (11) |
| C14 | 0.0298 (10) | 0.0491 (13) | 0.0365 (11) | −0.0019 (9) | 0.0136 (8) | −0.0015 (9) |
| C15 | 0.0490 (13) | 0.0568 (15) | 0.0501 (14) | 0.0037 (11) | 0.0141 (11) | −0.0028 (12) |
| C16 | 0.0615 (16) | 0.0654 (17) | 0.0603 (16) | −0.0112 (13) | 0.0261 (13) | −0.0215 (13) |
| C17 | 0.0562 (15) | 0.092 (2) | 0.0387 (13) | −0.0195 (15) | 0.0123 (11) | −0.0051 (14) |
| C18 | 0.0600 (16) | 0.0763 (19) | 0.0468 (14) | −0.0068 (13) | 0.0035 (12) | 0.0123 (13) |
| C19 | 0.0496 (13) | 0.0522 (14) | 0.0455 (13) | −0.0026 (11) | 0.0110 (10) | 0.0046 (11) |
| C20 | 0.0369 (11) | 0.0449 (12) | 0.0393 (12) | 0.0016 (9) | 0.0122 (9) | −0.0039 (9) |
| C21 | 0.0421 (12) | 0.0775 (18) | 0.0470 (14) | 0.0041 (12) | 0.0137 (11) | −0.0002 (12) |
| C22 | 0.0405 (13) | 0.099 (2) | 0.0657 (18) | 0.0000 (13) | 0.0214 (12) | −0.0073 (15) |
| C23 | 0.0624 (16) | 0.083 (2) | 0.0653 (18) | 0.0023 (14) | 0.0404 (14) | −0.0014 (14) |
| C24 | 0.0645 (16) | 0.0813 (19) | 0.0476 (14) | 0.0096 (14) | 0.0254 (12) | 0.0091 (13) |
| C25 | 0.0429 (12) | 0.0707 (17) | 0.0434 (13) | 0.0104 (11) | 0.0146 (10) | 0.0034 (11) |
Geometric parameters (Å, º)
| O1—C1 | 1.218 (2) | C12—C13 | 1.384 (3) |
| O2—C7 | 1.217 (2) | C12—H12A | 0.9300 |
| C1—C6 | 1.461 (3) | C13—H13A | 0.9300 |
| C1—C2 | 1.530 (3) | C14—C15 | 1.385 (3) |
| C2—C7 | 1.530 (3) | C14—C19 | 1.389 (3) |
| C2—C3 | 1.533 (3) | C15—C16 | 1.393 (3) |
| C2—H2A | 0.9800 | C15—H15A | 0.9300 |
| C3—C14 | 1.513 (3) | C16—C17 | 1.366 (4) |
| C3—C4 | 1.530 (3) | C16—H16A | 0.9300 |
| C3—H3A | 0.9800 | C17—C18 | 1.371 (4) |
| C4—C5 | 1.501 (3) | C17—H17A | 0.9300 |
| C4—H4A | 0.9700 | C18—C19 | 1.381 (3) |
| C4—H4B | 0.9700 | C18—H18A | 0.9300 |
| C5—C6 | 1.335 (3) | C19—H19A | 0.9300 |
| C5—C20 | 1.487 (3) | C20—C25 | 1.388 (3) |
| C6—H6A | 0.9300 | C20—C21 | 1.388 (3) |
| C7—C8 | 1.487 (3) | C21—C22 | 1.378 (3) |
| C8—C13 | 1.387 (3) | C21—H21A | 0.9300 |
| C8—C9 | 1.396 (3) | C22—C23 | 1.367 (4) |
| C9—C10 | 1.376 (3) | C22—H22A | 0.9300 |
| C9—H9A | 0.9300 | C23—C24 | 1.370 (3) |
| C10—C11 | 1.374 (4) | C23—H23A | 0.9300 |
| C10—H10A | 0.9300 | C24—C25 | 1.379 (3) |
| C11—C12 | 1.378 (3) | C24—H24A | 0.9300 |
| C11—H11A | 0.9300 | C25—H25A | 0.9300 |
| O1—C1—C6 | 121.6 (2) | C11—C12—C13 | 120.3 (2) |
| O1—C1—C2 | 120.64 (19) | C11—C12—H12A | 119.8 |
| C6—C1—C2 | 117.80 (17) | C13—C12—H12A | 119.8 |
| C1—C2—C7 | 108.05 (16) | C12—C13—C8 | 120.4 (2) |
| C1—C2—C3 | 111.34 (16) | C12—C13—H13A | 119.8 |
| C7—C2—C3 | 111.64 (17) | C8—C13—H13A | 119.8 |
| C1—C2—H2A | 108.6 | C15—C14—C19 | 117.7 (2) |
| C7—C2—H2A | 108.6 | C15—C14—C3 | 121.83 (19) |
| C3—C2—H2A | 108.6 | C19—C14—C3 | 120.35 (19) |
| C14—C3—C4 | 110.59 (16) | C14—C15—C16 | 120.5 (2) |
| C14—C3—C2 | 114.35 (16) | C14—C15—H15A | 119.7 |
| C4—C3—C2 | 109.83 (16) | C16—C15—H15A | 119.7 |
| C14—C3—H3A | 107.2 | C17—C16—C15 | 121.0 (2) |
| C4—C3—H3A | 107.2 | C17—C16—H16A | 119.5 |
| C2—C3—H3A | 107.2 | C15—C16—H16A | 119.5 |
| C5—C4—C3 | 113.23 (17) | C16—C17—C18 | 118.8 (2) |
| C5—C4—H4A | 108.9 | C16—C17—H17A | 120.6 |
| C3—C4—H4A | 108.9 | C18—C17—H17A | 120.6 |
| C5—C4—H4B | 108.9 | C17—C18—C19 | 120.8 (2) |
| C3—C4—H4B | 108.9 | C17—C18—H18A | 119.6 |
| H4A—C4—H4B | 107.7 | C19—C18—H18A | 119.6 |
| C6—C5—C20 | 122.24 (19) | C18—C19—C14 | 121.1 (2) |
| C6—C5—C4 | 119.54 (18) | C18—C19—H19A | 119.5 |
| C20—C5—C4 | 118.20 (17) | C14—C19—H19A | 119.5 |
| C5—C6—C1 | 124.03 (19) | C25—C20—C21 | 117.5 (2) |
| C5—C6—H6A | 118.0 | C25—C20—C5 | 120.77 (18) |
| C1—C6—H6A | 118.0 | C21—C20—C5 | 121.71 (19) |
| O2—C7—C8 | 120.30 (19) | C22—C21—C20 | 121.5 (2) |
| O2—C7—C2 | 118.76 (18) | C22—C21—H21A | 119.3 |
| C8—C7—C2 | 120.94 (19) | C20—C21—H21A | 119.3 |
| C13—C8—C9 | 118.4 (2) | C23—C22—C21 | 120.0 (2) |
| C13—C8—C7 | 123.14 (19) | C23—C22—H22A | 120.0 |
| C9—C8—C7 | 118.4 (2) | C21—C22—H22A | 120.0 |
| C10—C9—C8 | 120.8 (2) | C22—C23—C24 | 119.6 (2) |
| C10—C9—H9A | 119.6 | C22—C23—H23A | 120.2 |
| C8—C9—H9A | 119.6 | C24—C23—H23A | 120.2 |
| C11—C10—C9 | 120.2 (2) | C23—C24—C25 | 120.7 (2) |
| C11—C10—H10A | 119.9 | C23—C24—H24A | 119.6 |
| C9—C10—H10A | 119.9 | C25—C24—H24A | 119.6 |
| C10—C11—C12 | 119.9 (2) | C24—C25—C20 | 120.6 (2) |
| C10—C11—H11A | 120.1 | C24—C25—H25A | 119.7 |
| C12—C11—H11A | 120.1 | C20—C25—H25A | 119.7 |
| O1—C1—C2—C7 | −31.1 (3) | C10—C11—C12—C13 | 1.0 (4) |
| C6—C1—C2—C7 | 148.64 (19) | C11—C12—C13—C8 | −0.8 (4) |
| O1—C1—C2—C3 | −154.1 (2) | C9—C8—C13—C12 | 0.0 (3) |
| C6—C1—C2—C3 | 25.7 (3) | C7—C8—C13—C12 | −179.4 (2) |
| C1—C2—C3—C14 | −176.81 (17) | C4—C3—C14—C15 | −63.8 (2) |
| C7—C2—C3—C14 | 62.3 (2) | C2—C3—C14—C15 | 60.8 (3) |
| C1—C2—C3—C4 | −51.8 (2) | C4—C3—C14—C19 | 112.4 (2) |
| C7—C2—C3—C4 | −172.67 (17) | C2—C3—C14—C19 | −123.0 (2) |
| C14—C3—C4—C5 | −179.34 (18) | C19—C14—C15—C16 | −0.4 (3) |
| C2—C3—C4—C5 | 53.5 (2) | C3—C14—C15—C16 | 175.84 (19) |
| C3—C4—C5—C6 | −27.3 (3) | C14—C15—C16—C17 | 0.7 (3) |
| C3—C4—C5—C20 | 153.97 (19) | C15—C16—C17—C18 | −0.6 (4) |
| C20—C5—C6—C1 | 177.5 (2) | C16—C17—C18—C19 | 0.3 (4) |
| C4—C5—C6—C1 | −1.2 (3) | C17—C18—C19—C14 | −0.1 (4) |
| O1—C1—C6—C5 | −178.4 (2) | C15—C14—C19—C18 | 0.1 (3) |
| C2—C1—C6—C5 | 1.8 (3) | C3—C14—C19—C18 | −176.2 (2) |
| C1—C2—C7—O2 | −83.9 (2) | C6—C5—C20—C25 | −30.6 (3) |
| C3—C2—C7—O2 | 38.9 (3) | C4—C5—C20—C25 | 148.1 (2) |
| C1—C2—C7—C8 | 95.4 (2) | C6—C5—C20—C21 | 149.3 (2) |
| C3—C2—C7—C8 | −141.80 (19) | C4—C5—C20—C21 | −32.0 (3) |
| O2—C7—C8—C13 | 169.2 (2) | C25—C20—C21—C22 | 0.7 (4) |
| C2—C7—C8—C13 | −10.2 (3) | C5—C20—C21—C22 | −179.2 (2) |
| O2—C7—C8—C9 | −10.3 (3) | C20—C21—C22—C23 | −0.5 (4) |
| C2—C7—C8—C9 | 170.39 (19) | C21—C22—C23—C24 | −0.1 (4) |
| C13—C8—C9—C10 | 0.5 (3) | C22—C23—C24—C25 | 0.4 (4) |
| C7—C8—C9—C10 | 180.0 (2) | C23—C24—C25—C20 | −0.2 (4) |
| C8—C9—C10—C11 | −0.3 (4) | C21—C20—C25—C24 | −0.4 (4) |
| C9—C10—C11—C12 | −0.5 (4) | C5—C20—C25—C24 | 179.6 (2) |
Hydrogen-bond geometry (Å, º)
Cg2 and Cg3 are the centroids of the C8–C13 and C14–C19 phenyl rings, respectively.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C2—H2A···O2i | 0.98 | 2.50 | 3.251 (3) | 133 |
| C15—H15A···O1i | 0.93 | 2.55 | 3.369 (3) | 148 |
| C22—H22A···O1ii | 0.93 | 2.54 | 3.472 (3) | 175 |
| C11—H11A···Cg3iii | 0.93 | 2.88 | 3.717 (2) | 150 |
| C24—H24A···Cg2iv | 0.93 | 2.78 | 3.667 (3) | 159 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x−1, y, z; (iii) x+1, y, z; (iv) x−3/2, −y−1/2, z−1/2.
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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/S2056989020005381/is5536sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989020005381/is5536Isup2.hkl
CCDC reference: 1983451
Additional supporting information: crystallographic information; 3D view; checkCIF report