Synthesis and crystal structure of (2E)-1-[3,5-bis­(benz­yloxy)phen­yl]-3-(4-eth­oxy­phen­yl)prop-2-en-1-one

Jeyashri, K.R.; Logeshwari, G.; Rajapandiyan, U.; Sivakumar, K.; Selvanayagam, S.; Manikandan, H.; Kaviyarasu, K.

doi:10.1107/S2056989024007552

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ISSN: 2056-9890

Volume 80| Part 9| September 2024| Pages 913-915

https://doi.org/10.1107/S2056989024007552

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Synthesis and crystal structure of (2E)-1-[3,5-bis(benzyloxy)phenyl]-3-(4-ethoxyphenyl)prop-2-en-1-one

K. R. Jeyashri,^a G. Logeshwari,^a U. Rajapandiyan,^a K. Sivakumar,^b S. Selvanayagam,^c ‡ H. Manikandan ^a ^* and K. Kaviyarasu ^d

^aDepartment of Chemistry, Annamalai University, Annamalainagar, Chidambaram 608 002, India, ^bDepartment of Chemistry, Sri Chandrasekharendra Saraswathi Viswa Mahavidyalaya, (Deeded to be University), Kanchipuram 631 561, India, ^cPG & Research Department of Physics, Government Arts College, Melur 625 106, India, and ^dNanosciences/Nanotechnology Laboratories, University of South Africa (UNISA), Pretoria, South Africa
^*Correspondence e-mail: profmani.au@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 8 July 2024; accepted 31 July 2024; online 6 August 2024)

In the title compound, C₃₁H₂₈O₄, the phenyl rings of the chalcone unit subtend a dihedral angle of 26.43 (10)°. The phenyl rings of the pendant benzyloxy groups are orientated at 75.57 (13) and 75.70 (10)° with respect to their attached ring. In the crystal, weak C—H⋯O and C—H⋯π interactions link the molecules. The intermolecular interactions were quantified and analysed using Hirshfeld surface analysis, which showed a breakdown into H⋯H (49.8%), H⋯C/C⋯H (33.8%) and H⋯O/O⋯H (13.6%) interactions with other types making negligible contributions.

Keywords: crystal structure; chalcone derivative; C—H⋯O interactions; Hirshfeld surface analysis.

CCDC reference: 2182630

1. Chemical context

Chalcones incorporate an α,β-unsaturated carbonyl (enone) bridge connecting two aromatic rings. The chalcone scaffold exhibits anti-cancer efficacy on various human cancer cells (Zhuang et al., 2017 ; Liu et al., 2022 ). DrugBank lists three chalcone-based drugs namely hesperidin methylchalcone (DrugBank: DB15943), dihydroxymethoxychalcone (DB14122) and 3-(4-hydroxyphenyl)prop-2-en-1-one (DB07500). In general, the anticancer efficacy of chalcones is enhanced by attaching different substitutents at ring A of the chalcone, which is attached to the C=O group (Mai et al., 2014 ). As part of our studies in this area, we have prepared and undertaken a single-crystal X-ray diffraction study of the title compound, C₃₁H₂₈O₄, (I), and the results are presented here.

2. Structural commentary

The molecular structure of (I) is illustrated in Fig. 1. The C12–C17 and C19–C24 phenyl rings of the chalcone unit subtend a dihedral angle of 26.43 (10)°: the most significant twist occurs about the C11—C12 bond, as indicated by the C10—C11—C12—C13 torsion angle of −13.0 (3)°. The dihedral angles between the C19–C24 and C26–C31 pendant phenyl rings and their attached C12–C17 ring are 75.57 (13) and 75.70 (10)°, respectively. The C3—O1—C2—C1, C14—O4—C25—C26 and C16—O3—C18—C19 torsion angles of 177.2 (3), 176.21 (18) and 179.5 (2)°, respectively, indicate an anti conformation in each case.

Figure 1
The molecular structure of (I)

with displacement ellipsoids drawn at the 30% probability level.

3. Supramolecular features

In the crystal of (I), the molecules associate via weak C—H⋯O interactions (Table 1), forming C(15) chains propagating along [101] (Fig. 2). In addition, inversion-related molecules are linked by pairwise weak C—H⋯π interactions (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C26–C31 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O4ⁱ	0.96	2.64	3.227 (3)	119
C25—H25B⋯Cg1ⁱⁱ	0.97	2.68	3.398 (2)	132
Symmetry codes: (i) ; (ii) .

Figure 2
Detail of the packing of (I)

showing C—H⋯O interactions as dashed lines. For clarity H atoms not involved in these hydrogen bonds have been omitted.

Figure 3
Detail of the packing of (I)

showing C—H⋯π interactions as dashed lines.

4. Hirshfeld surface analysis

To further characterize the intermolecular interactions in (I), a Hirshfeld surface analysis was performed using Crystal Explorer 21 (Spackman et al., 2021 ) and the associated two dimensional fingerprint plots were generated. The HS mapped over d_norm in the range −0.09 to +1.53 a.u. is illustrated in Fig. 4, using colours to indicate contacts that are shorter (red areas), equal to (white areas), or longer than (blue areas) the sum of the van der Waals radii (Ashfaq et al., 2021 ).

Figure 4
A view of the Hirshfeld surface mapped over d_norm for (I)

The overall two-dimensional fingerprint plot, Fig. 5a, and those delineated into H⋯H interactions (49.8%), H⋯C/C⋯H (33.8%), H⋯O/O⋯H (13.6%), C⋯C (1.8%) and O⋯C/C⋯O (1%) interactions are illustrated in Fig. 5b–f, respectively, together with their relative contributions to the HS. The most important interaction is H⋯H, which is reflected in Fig. 5b as widely scattered points of high density due to the large hydrogen content of the molecule with the tip at d_e = d_i = 1.10 Å. As a result of the presence of C—H⋯O interactions, the H⋯O/O⋯H contacts contribute 13.6% to the overall crystal packing, as reflected in Fig. 5d with the tips at d_e + d_i = 2.50 Å.

Figure 5
Two-dimensional fingerprint plots for (I)

, showing (a) all interactions, and delineated into (b) H⋯H, (c) H⋯C/C⋯H, (d) H⋯O/O⋯H, (e) C⋯C and (f) O⋯C/C⋯O interactions.

5. Synthesis and crystallization

Equimolar concentrations of 3,5-dibenzyloxyacetophenone and 4-ethoxybenzaldehyde were dissolved in ethanol in separate reaction flasks and then mixed. Drop by drop, utilizing a magnetic stirring device, 2 ml of 10% sodium hydroxide in water were introduced at room temperature. The course of the process was tracked using thin-layer chromatography. After the process was complete, the resulting product was placed on crushed ice. The finished product was vacuum-filtered, dried, and then recrystallized from ethanol solution to yield colourless blocks of the title compound.

IR (cm⁻¹): 3032 aromatic C—H stretch, 2934 and 2875 aliphatic C—H stretch, 1651 C=O stretch, 1568 aromatic ring C=C stretch (see table in the supporting information).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were placed in idealized positions and allowed to ride on their parent atoms: C—H = 0.93–0.97 Å, with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₃₁H₂₈O₄
M_r	464.53
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	298
a, b, c (Å)	9.0494 (9), 10.0326 (11), 14.6932 (15)
α, β, γ (°)	100.153 (3), 107.292 (3), 90.789 (4)
V (Å³)	1250.6 (2)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.31 × 0.23 × 0.19

Data collection
Diffractometer	Bruker D8 Quest XRD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	30243, 5428, 3607
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.178, 1.05
No. of reflections	5428
No. of parameters	317
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.18
Computer programs: APEX3 and SAINT (Bruker, 2017 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2019/3 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2182630

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989024007552/hb8103sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989024007552/hb8103Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989024007552/hb8103Isup3.cml

checkCIF report

Computing details top

(2E)-1-[3,5-Bis(benzyloxy)phenyl]-3-(4-ethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₃₁H₂₈O₄	Z = 2
M_r = 464.53	F(000) = 492
Triclinic, P1	D_x = 1.234 Mg m⁻³
a = 9.0494 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0326 (11) Å	Cell parameters from 9430 reflections
c = 14.6932 (15) Å	θ = 2.3–26.6°
α = 100.153 (3)°	µ = 0.08 mm⁻¹
β = 107.292 (3)°	T = 298 K
γ = 90.789 (4)°	Block, colourless
V = 1250.6 (2) Å³	0.31 × 0.23 × 0.19 mm

Data collection top

Bruker D8 Quest XRD diffractometer	R_int = 0.037
Detector resolution: 7.3910 pixels mm^-1	θ_max = 27.0°, θ_min = 2.3°
ω and Phi Scans scans	h = −11→11
30243 measured reflections	k = −12→12
5428 independent reflections	l = −18→18
3607 reflections with I > 2σ(I)

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.178	w = 1/[σ²(F_o²) + (0.0755P)² + 0.344P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
5428 reflections	Δρ_max = 0.36 e Å⁻³
317 parameters	Δρ_min = −0.18 e Å⁻³

Special details top

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) top

	x	y	z	U_iso*/U_eq
O1	−0.14058 (19)	0.34912 (19)	−0.00351 (12)	0.0891 (5)
O2	0.16186 (19)	0.72402 (15)	0.58657 (11)	0.0798 (5)
O3	0.57910 (18)	0.67306 (14)	0.89498 (11)	0.0758 (5)
O4	0.58288 (19)	0.27603 (13)	0.68226 (10)	0.0781 (5)
C1	−0.1307 (4)	0.2055 (4)	−0.1454 (2)	0.1262 (13)
H1A	−0.151371	0.280342	−0.178933	0.189*
H1B	−0.226967	0.158707	−0.150531	0.189*
H1C	−0.069164	0.144122	−0.173877	0.189*
C2	−0.0474 (3)	0.2556 (3)	−0.04420 (19)	0.0904 (8)
H2A	−0.027085	0.180610	−0.009604	0.109*
H2AB	0.051245	0.301090	−0.038289	0.109*
C3	−0.0852 (2)	0.4030 (2)	0.09240 (16)	0.0674 (5)
C4	0.0551 (3)	0.3730 (2)	0.15297 (17)	0.0692 (6)
H4	0.117713	0.313490	0.128230	0.083*
C5	0.1007 (2)	0.4316 (2)	0.24907 (16)	0.0653 (5)
H5	0.194960	0.410658	0.288762	0.078*
C6	0.0118 (2)	0.52131 (19)	0.29011 (15)	0.0581 (5)
C7	−0.1280 (2)	0.5512 (2)	0.22718 (17)	0.0706 (6)
H7	−0.189955	0.611871	0.251480	0.085*
C8	−0.1756 (3)	0.4931 (3)	0.13069 (17)	0.0774 (6)
H8	−0.269403	0.514352	0.090561	0.093*
C9	0.0606 (2)	0.5819 (2)	0.39198 (15)	0.0611 (5)
H9	−0.000981	0.647173	0.411977	0.073*
C10	0.1840 (2)	0.5545 (2)	0.46044 (15)	0.0619 (5)
H10	0.247017	0.488795	0.442843	0.074*
C11	0.2253 (2)	0.62323 (18)	0.56229 (15)	0.0572 (5)
C12	0.3502 (2)	0.57021 (17)	0.63744 (14)	0.0535 (4)
C13	0.4072 (2)	0.44298 (18)	0.61769 (14)	0.0569 (5)
H13	0.372300	0.389726	0.555824	0.068*
C14	0.5168 (2)	0.39755 (18)	0.69199 (15)	0.0597 (5)
C15	0.5686 (2)	0.47618 (19)	0.78386 (14)	0.0613 (5)
H15	0.639925	0.443738	0.833530	0.074*
C16	0.5144 (2)	0.60315 (19)	0.80212 (14)	0.0584 (5)
C17	0.4042 (2)	0.65032 (18)	0.72948 (14)	0.0584 (5)
H17	0.366639	0.735155	0.742260	0.070*
C18	0.5246 (3)	0.8021 (2)	0.92022 (18)	0.0908 (8)
H18A	0.413970	0.793221	0.911087	0.109*
H18B	0.542890	0.862592	0.879393	0.109*
C19	0.6105 (3)	0.8580 (2)	1.02462 (17)	0.0718 (6)
C20	0.5696 (3)	0.8133 (3)	1.0964 (2)	0.0881 (7)
H20	0.490407	0.745243	1.080563	0.106*
C21	0.6443 (4)	0.8678 (3)	1.1924 (2)	0.1037 (10)
H21	0.615398	0.836038	1.240799	0.124*
C22	0.7596 (4)	0.9672 (4)	1.2169 (2)	0.1080 (11)
H22	0.808981	1.004115	1.281899	0.130*
C23	0.8029 (3)	1.0130 (3)	1.1459 (3)	0.1034 (10)
H23	0.882143	1.081096	1.162282	0.124*
C24	0.7284 (3)	0.9579 (3)	1.0495 (2)	0.0852 (7)
H24	0.758359	0.988800	1.001161	0.102*
C25	0.5493 (3)	0.19191 (19)	0.58876 (15)	0.0664 (6)
H25A	0.574903	0.241425	0.543764	0.080*
H25B	0.439988	0.162010	0.563792	0.080*
C26	0.6465 (2)	0.07200 (18)	0.60074 (14)	0.0586 (5)
C27	0.7704 (3)	0.0568 (2)	0.56452 (17)	0.0686 (6)
H27	0.794339	0.121305	0.531744	0.082*
C28	0.8599 (3)	−0.0535 (2)	0.57641 (18)	0.0731 (6)
H28	0.942723	−0.062797	0.551033	0.088*
C29	0.8279 (3)	−0.1484 (2)	0.62481 (17)	0.0698 (6)
H29	0.889257	−0.221547	0.633478	0.084*
C30	0.7042 (3)	−0.1351 (2)	0.66067 (18)	0.0749 (6)
H30	0.681177	−0.199693	0.693631	0.090*
C31	0.6136 (3)	−0.0260 (2)	0.64803 (17)	0.0705 (6)
H31	0.529072	−0.018708	0.671861	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0745 (10)	0.1103 (13)	0.0696 (10)	0.0256 (9)	0.0120 (8)	−0.0008 (9)
O2	0.0974 (11)	0.0644 (9)	0.0736 (10)	0.0421 (8)	0.0194 (8)	0.0118 (7)
O3	0.0805 (10)	0.0589 (8)	0.0680 (9)	0.0309 (7)	0.0050 (7)	−0.0116 (7)
O4	0.0979 (11)	0.0489 (8)	0.0667 (9)	0.0363 (7)	0.0013 (8)	−0.0048 (6)
C1	0.113 (2)	0.159 (3)	0.085 (2)	0.057 (2)	0.0089 (18)	−0.001 (2)
C2	0.0876 (17)	0.0991 (19)	0.0795 (17)	0.0304 (15)	0.0240 (14)	0.0043 (14)
C3	0.0615 (12)	0.0707 (13)	0.0659 (13)	0.0100 (10)	0.0160 (10)	0.0074 (10)
C4	0.0655 (13)	0.0660 (13)	0.0748 (14)	0.0222 (10)	0.0188 (11)	0.0128 (11)
C5	0.0616 (12)	0.0615 (12)	0.0712 (14)	0.0188 (9)	0.0138 (10)	0.0181 (10)
C6	0.0555 (11)	0.0540 (10)	0.0658 (12)	0.0094 (9)	0.0167 (9)	0.0164 (9)
C7	0.0589 (12)	0.0798 (14)	0.0729 (14)	0.0245 (11)	0.0189 (11)	0.0143 (11)
C8	0.0568 (12)	0.0998 (17)	0.0706 (14)	0.0260 (12)	0.0119 (11)	0.0151 (12)
C9	0.0633 (12)	0.0542 (11)	0.0673 (13)	0.0133 (9)	0.0193 (10)	0.0154 (9)
C10	0.0686 (12)	0.0507 (10)	0.0665 (13)	0.0186 (9)	0.0186 (10)	0.0134 (9)
C11	0.0623 (11)	0.0447 (9)	0.0647 (12)	0.0136 (8)	0.0189 (9)	0.0105 (8)
C12	0.0567 (10)	0.0415 (9)	0.0623 (11)	0.0122 (8)	0.0182 (9)	0.0090 (8)
C13	0.0650 (11)	0.0412 (9)	0.0581 (11)	0.0133 (8)	0.0129 (9)	0.0019 (8)
C14	0.0653 (12)	0.0403 (9)	0.0672 (12)	0.0183 (8)	0.0143 (10)	0.0025 (8)
C15	0.0645 (12)	0.0494 (10)	0.0616 (12)	0.0196 (9)	0.0101 (9)	0.0029 (9)
C16	0.0613 (11)	0.0463 (10)	0.0603 (11)	0.0135 (8)	0.0139 (9)	−0.0022 (8)
C17	0.0619 (11)	0.0413 (9)	0.0684 (12)	0.0170 (8)	0.0186 (10)	0.0023 (8)
C18	0.1038 (18)	0.0631 (13)	0.0800 (16)	0.0407 (13)	0.0040 (13)	−0.0145 (11)
C19	0.0734 (14)	0.0559 (12)	0.0712 (14)	0.0292 (11)	0.0100 (11)	−0.0080 (10)
C20	0.0917 (18)	0.0732 (15)	0.0921 (19)	0.0143 (13)	0.0280 (15)	−0.0044 (14)
C21	0.132 (3)	0.100 (2)	0.0829 (19)	0.047 (2)	0.0413 (19)	0.0101 (16)
C22	0.108 (2)	0.099 (2)	0.0810 (19)	0.0477 (19)	−0.0079 (18)	−0.0167 (17)
C23	0.0765 (17)	0.0812 (18)	0.119 (3)	0.0129 (14)	−0.0030 (17)	−0.0133 (18)
C24	0.0812 (16)	0.0728 (15)	0.0953 (19)	0.0221 (13)	0.0228 (14)	0.0054 (13)
C25	0.0778 (13)	0.0437 (10)	0.0647 (12)	0.0206 (9)	0.0090 (10)	−0.0030 (9)
C26	0.0655 (12)	0.0383 (9)	0.0620 (11)	0.0132 (8)	0.0103 (9)	−0.0014 (8)
C27	0.0686 (13)	0.0488 (11)	0.0873 (15)	0.0067 (9)	0.0210 (11)	0.0144 (10)
C28	0.0607 (12)	0.0635 (13)	0.0987 (17)	0.0162 (10)	0.0291 (12)	0.0154 (12)
C29	0.0678 (13)	0.0503 (11)	0.0880 (15)	0.0219 (9)	0.0192 (11)	0.0110 (10)
C30	0.0898 (16)	0.0542 (12)	0.0903 (16)	0.0246 (11)	0.0363 (13)	0.0220 (11)
C31	0.0802 (14)	0.0577 (12)	0.0816 (15)	0.0263 (10)	0.0362 (12)	0.0118 (11)

Geometric parameters (Å, º) top

O1—C3	1.354 (3)	C14—C15	1.379 (3)
O1—C2	1.440 (3)	C15—C16	1.382 (2)
O2—C11	1.221 (2)	C15—H15	0.9300
O3—C16	1.368 (2)	C16—C17	1.384 (3)
O3—C18	1.419 (2)	C17—H17	0.9300
O4—C14	1.369 (2)	C18—C19	1.499 (3)
O4—C25	1.424 (2)	C18—H18A	0.9700
C1—C2	1.446 (4)	C18—H18B	0.9700
C1—H1A	0.9600	C19—C20	1.358 (4)
C1—H1B	0.9600	C19—C24	1.374 (4)
C1—H1C	0.9600	C20—C21	1.377 (4)
C2—H2A	0.9700	C20—H20	0.9300
C2—H2AB	0.9700	C21—C22	1.354 (5)
C3—C8	1.385 (3)	C21—H21	0.9300
C3—C4	1.388 (3)	C22—C23	1.364 (5)
C4—C5	1.365 (3)	C22—H22	0.9300
C4—H4	0.9300	C23—C24	1.383 (4)
C5—C6	1.392 (3)	C23—H23	0.9300
C5—H5	0.9300	C24—H24	0.9300
C6—C7	1.399 (3)	C25—C26	1.504 (2)
C6—C9	1.444 (3)	C25—H25A	0.9700
C7—C8	1.369 (3)	C25—H25B	0.9700
C7—H7	0.9300	C26—C31	1.376 (3)
C8—H8	0.9300	C26—C27	1.376 (3)
C9—C10	1.331 (3)	C27—C28	1.386 (3)
C9—H9	0.9300	C27—H27	0.9300
C10—C11	1.467 (3)	C28—C29	1.360 (3)
C10—H10	0.9300	C28—H28	0.9300
C11—C12	1.504 (3)	C29—C30	1.370 (3)
C12—C17	1.388 (3)	C29—H29	0.9300
C12—C13	1.399 (2)	C30—C31	1.382 (3)
C13—C14	1.388 (3)	C30—H30	0.9300
C13—H13	0.9300	C31—H31	0.9300

C3—O1—C2	117.52 (18)	O3—C16—C15	114.35 (17)
C16—O3—C18	117.54 (16)	O3—C16—C17	125.27 (16)
C14—O4—C25	119.51 (15)	C15—C16—C17	120.38 (18)
C2—C1—H1A	109.5	C16—C17—C12	119.58 (16)
C2—C1—H1B	109.5	C16—C17—H17	120.2
H1A—C1—H1B	109.5	C12—C17—H17	120.2
C2—C1—H1C	109.5	O3—C18—C19	107.89 (17)
H1A—C1—H1C	109.5	O3—C18—H18A	110.1
H1B—C1—H1C	109.5	C19—C18—H18A	110.1
O1—C2—C1	108.5 (2)	O3—C18—H18B	110.1
O1—C2—H2A	110.0	C19—C18—H18B	110.1
C1—C2—H2A	110.0	H18A—C18—H18B	108.4
O1—C2—H2AB	110.0	C20—C19—C24	118.8 (2)
C1—C2—H2AB	110.0	C20—C19—C18	120.3 (3)
H2A—C2—H2AB	108.4	C24—C19—C18	120.9 (3)
O1—C3—C8	117.02 (19)	C19—C20—C21	120.6 (3)
O1—C3—C4	123.8 (2)	C19—C20—H20	119.7
C8—C3—C4	119.2 (2)	C21—C20—H20	119.7
C5—C4—C3	119.6 (2)	C22—C21—C20	120.6 (3)
C5—C4—H4	120.2	C22—C21—H21	119.7
C3—C4—H4	120.2	C20—C21—H21	119.7
C4—C5—C6	122.75 (19)	C21—C22—C23	119.7 (3)
C4—C5—H5	118.6	C21—C22—H22	120.2
C6—C5—H5	118.6	C23—C22—H22	120.2
C5—C6—C7	116.49 (19)	C22—C23—C24	119.8 (3)
C5—C6—C9	122.29 (18)	C22—C23—H23	120.1
C7—C6—C9	121.22 (19)	C24—C23—H23	120.1
C8—C7—C6	121.5 (2)	C19—C24—C23	120.6 (3)
C8—C7—H7	119.2	C19—C24—H24	119.7
C6—C7—H7	119.2	C23—C24—H24	119.7
C7—C8—C3	120.5 (2)	O4—C25—C26	106.86 (15)
C7—C8—H8	119.8	O4—C25—H25A	110.4
C3—C8—H8	119.8	C26—C25—H25A	110.4
C10—C9—C6	127.10 (19)	O4—C25—H25B	110.4
C10—C9—H9	116.4	C26—C25—H25B	110.4
C6—C9—H9	116.4	H25A—C25—H25B	108.6
C9—C10—C11	123.09 (19)	C31—C26—C27	118.09 (18)
C9—C10—H10	118.5	C31—C26—C25	120.9 (2)
C11—C10—H10	118.5	C27—C26—C25	121.05 (19)
O2—C11—C10	121.00 (18)	C26—C27—C28	120.7 (2)
O2—C11—C12	119.63 (18)	C26—C27—H27	119.7
C10—C11—C12	119.36 (16)	C28—C27—H27	119.7
C17—C12—C13	120.41 (17)	C29—C28—C27	120.7 (2)
C17—C12—C11	117.54 (16)	C29—C28—H28	119.7
C13—C12—C11	122.00 (17)	C27—C28—H28	119.7
C14—C13—C12	118.88 (18)	C28—C29—C30	119.28 (19)
C14—C13—H13	120.6	C28—C29—H29	120.4
C12—C13—H13	120.6	C30—C29—H29	120.4
O4—C14—C15	114.51 (16)	C29—C30—C31	120.2 (2)
O4—C14—C13	124.79 (17)	C29—C30—H30	119.9
C15—C14—C13	120.70 (16)	C31—C30—H30	119.9
C16—C15—C14	120.01 (18)	C26—C31—C30	121.0 (2)
C16—C15—H15	120.0	C26—C31—H31	119.5
C14—C15—H15	120.0	C30—C31—H31	119.5

C3—O1—C2—C1	177.2 (3)	C18—O3—C16—C15	−177.5 (2)
C2—O1—C3—C8	179.8 (2)	C18—O3—C16—C17	2.7 (3)
C2—O1—C3—C4	−0.1 (4)	C14—C15—C16—O3	−177.57 (19)
O1—C3—C4—C5	−179.4 (2)	C14—C15—C16—C17	2.2 (3)
C8—C3—C4—C5	0.7 (3)	O3—C16—C17—C12	178.65 (19)
C3—C4—C5—C6	0.0 (3)	C15—C16—C17—C12	−1.1 (3)
C4—C5—C6—C7	−0.9 (3)	C13—C12—C17—C16	−0.5 (3)
C4—C5—C6—C9	179.5 (2)	C11—C12—C17—C16	177.29 (18)
C5—C6—C7—C8	1.1 (3)	C16—O3—C18—C19	179.5 (2)
C9—C6—C7—C8	−179.4 (2)	O3—C18—C19—C20	−78.4 (3)
C6—C7—C8—C3	−0.4 (4)	O3—C18—C19—C24	103.6 (3)
O1—C3—C8—C7	179.6 (2)	C24—C19—C20—C21	0.4 (3)
C4—C3—C8—C7	−0.5 (4)	C18—C19—C20—C21	−177.6 (2)
C5—C6—C9—C10	−5.9 (3)	C19—C20—C21—C22	0.2 (4)
C7—C6—C9—C10	174.6 (2)	C20—C21—C22—C23	−0.5 (4)
C6—C9—C10—C11	179.11 (19)	C21—C22—C23—C24	0.2 (4)
C9—C10—C11—O2	−11.5 (3)	C20—C19—C24—C23	−0.7 (3)
C9—C10—C11—C12	169.80 (19)	C18—C19—C24—C23	177.3 (2)
O2—C11—C12—C17	−9.3 (3)	C22—C23—C24—C19	0.4 (4)
C10—C11—C12—C17	169.33 (19)	C14—O4—C25—C26	176.21 (18)
O2—C11—C12—C13	168.4 (2)	O4—C25—C26—C31	70.9 (2)
C10—C11—C12—C13	−13.0 (3)	O4—C25—C26—C27	−109.3 (2)
C17—C12—C13—C14	1.0 (3)	C31—C26—C27—C28	−0.6 (3)
C11—C12—C13—C14	−176.69 (18)	C25—C26—C27—C28	179.60 (19)
C25—O4—C14—C15	−174.2 (2)	C26—C27—C28—C29	−0.6 (3)
C25—O4—C14—C13	5.3 (3)	C27—C28—C29—C30	1.0 (4)
C12—C13—C14—O4	−179.38 (19)	C28—C29—C30—C31	−0.3 (4)
C12—C13—C14—C15	0.1 (3)	C27—C26—C31—C30	1.3 (3)
O4—C14—C15—C16	177.83 (19)	C25—C26—C31—C30	−178.9 (2)
C13—C14—C15—C16	−1.7 (3)	C29—C30—C31—C26	−0.9 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C26–C31 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O4ⁱ	0.96	2.64	3.227 (3)	119
C25—H25B···Cg1ⁱⁱ	0.97	2.68	3.398 (2)	132

Symmetry codes: (i) x−1, y, z−1; (ii) −x+1, −y, −z+1.

IR spectroscopic data (cm^–1) top

Assignments	1
δ (CH₂) rocking	696(m)
δ (C-Cl)	-
δ (C-H)(Ar)	835(m)
ν (C-O-C)	1049(s)
δ (C-H) of –OCH₂CH₃	1328(m)
δ (C-H) of –OCH₃	-
ν (C-C)	1433(m)
ν (C=C)	1568(s)
ν (C=O)	1651(s)
ν (C-H) (aliphatic)	2934(w)
ν (C-H)(aromatic)	3032(w)

ν -stretching, δ-bending, a-antisymmetry, s-symmetry, (w)-weak intensity, (m)-medium peak, (s)-strong peak

Footnotes

‡Additional correspondence author, e-mail: s_selvanayagam@rediffmail.com.

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