Crystal structure of (E)-3-(2-hy­droxy-4-methyl­phen­yl)-1-(2,4,6-tri­meth­oxy­phen­yl)prop-2-en-1-one

Jumaah, M.; Kwong, H.C.; Khairuddean, M.

doi:10.1107/S2056989019011289

research communications

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 75| Part 9| September 2019| Pages 1379-1382

https://doi.org/10.1107/S2056989019011289

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Crystal structure of (E)-3-(2-hydroxy-4-methylphenyl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one

Maadh Jumaah,^a Huey Chong Kwong ^b and Melati Khairuddean ^a ^*

^aSchool of Chemical Sciences, Universiti Sains Malaysia, Penang 11800 USM, Malaysia, and ^bDepartment of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor Darul Ehsan, Malaysia
^*Correspondence e-mail: melati@usm.my

Edited by J. Jasinski, Keene State College, USA (Received 24 July 2019; accepted 13 August 2019; online 30 August 2019)

The title chalcone derivative, C₁₉H₂₀O₅, adopts a trans configuration with respect to the olefinic C=C double bond. The 2-hydroxy-4-methylphenyl ring is coplanar with the attached enone bridge [torsion angle = −179.96 (14)°], where this plane is nearly perpendicular to the 2,4,6-trimethoxyphenyl ring [dihedral angle = 75.81 (8)°]. In the crystal, molecules are linked into chains propagating along [010] by an O—H⋯O hydrogen bond. These chains are further connected into centrosymmetric dimer chains via weak C—H⋯O interactions. The conformations of related chalcone derivatives are surveyed and all of these structures adopt a skeleton with two almost orthogonal aromatic rings.

Keywords: crystal structure; chalcone; enone bridge; O—H⋯O interaction; data survey.

CCDC reference: 1946810

1. Chemical context

Chalcones (1,3-diarylprop-2-en-1-ones) are precursors of flavonoids and isoflavonoids in the plant kingdom (Ni et al., 2004 ; Sahu et al., 2012 ). Structurally, they consist of two aryl groups linked by an α, β-unsaturated ketone system (Ibrahim et al., 2012 ; Kumar et al., 2013 ), whereby the aryl groups can carry a variety of substituents such as hydroxyl, methoxy and alkenyl groups, which are by far the most commonly encountered ones in nature. With their structural simplicity and the associated ease of synthesis, chalcone compounds have attracted a considerable amount of attention because of their important pharmacological properties such as anti-oxidative (Aoki et al., 2008 ), anti-inflammatory (Israf et al., 2007 ), anti-gout (Jang et al., 2014 ), anti-histaminic (Yamamoto et al., 2004 ), anti-obesity (Birari et al., 2011 ), anti-protozoal (Chen et al., 1993 ), hypnotic (Cho et al., 2011 ) and anti-spasmodic (Sato et al., 2007 ) effects. In a continuation of our ongoing research on the properties of various chalcone derivatives (Sim et al., 2017 , Kwong et al., 2018 ), we report herein the synthesis and crystal structure determination of the title compound, C₁₉H₂₀O₅, (I).

2. Structural commentary

The title chalcone derivative (I), crystallizes in the centrosymmetric triclinic space group P $[\overline{1}]$ and its asymmetric unit consists of a single unique molecule (Fig. 1). This molecule is constructed of two substituted aromatic rings (2-hydroxy-4-methylphenyl and 2,4,6-trimethoxyphenyl) and an enone (–CH=CH—(C=O)–) connecting bridge. In the enone bridge, the C6—C7, C8—C9 and C9—C10 bond lengths of 1.446 (2), 1.441 (2) and 1.504 (2) Å, respectively, confirm their single-bond character, whereas the C7=C8 and C9=O2 bond lengths of 1.340 (2) and 1.2255 (17) Å, respectively, confirm the presence of a double bond. In addition, the C6—C7—C8 and C8—C9—C10 bond angles of 128.71 (13) and 119.47 (11)°, respectively, are consistent with the sp² hybridization of atoms C7, C8 and C9 (Kerr et al., 2001 ; Loghmani-Khouzani et al., 2009 ; Grealis et al., 2013 ). As the olefinic double bond C7=C8 adopts a trans configuration [C6—C7—C8—C9 torsion angle = −179.96 (14)°], the structural conformation of (I) can be defined by three torsion angles. The torsion angles between the 2-hydroxy-4-methylphenyl ring and the olefinic double bond (C5—C6—C7—C8, τ₁), between the olefinic double bond and the carbonyl group (C7—C8—C9—C10, τ₂) and between the carbonyl group and the 2,4,6-trimethoxyphenyl ring (C8—C9—C10—C11, τ₃) are shown in Fig. 2. The torsion angles τ₁ and τ₂ are approximately ±180° or 0° [τ₁ = −179.15 (14)° and τ₂ = −0.8 (2)°], indicating that the 2-hydroxy-4-methylphenyl ring and the enone bridge are coplanar. In contrast, the carbonyl group is nearly perpendicular to the attached 2,4,6-trimethoxyphenyl ring, as τ₃ is 76.87 (19)°. In general, the molecule of (I) can be considered as two individual planes, the first comprising the 2-hydroxy-4-methylphenyl ring and the enone bridge [maximum deviation of 0.0021 (2) Å for atom C19], and the second the 2,4,6-trimethoxyphenyl ring [maximum deviation of 0.0059 (2) Å for atom C18]. These two mean planes form a dihedral angle of 75.84 (4)°, hence the molecule of (I) possesses a skeleton with two almost orthogonal aromatic rings.

Figure 1
The title molecule with the atom-labelling scheme and displacement ellipsoids drawn at the 50% ellipsoid probability level.

Figure 2
General chemical diagram showing torsion angles, τ₁, τ₂ and τ₃.

3. Supramolecular features

In the crystal, the molecules are linked into chains parallel to the b axis via classical O1—H1B⋯O2ⁱ hydrogen bonds (Fig. 3a). These chains are further connected into inversion-related dimeric chains by weak C17—H17A⋯O1ⁱⁱ intermolecular interactions (Fig. 3b, Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯O2ⁱ	0.82	1.88	2.6653 (15)	161
C17—H17A⋯O1ⁱⁱ	0.96	2.70	3.520 (2)	144
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y, -z.

Figure 3
Views of (a) a chain of molecules linked by O—H⋯O hydrogen bonds (shown as cyan dotted lines) and (b) a dimeric chain formed by weak C—H⋯O interactions (shown as magenta dotted lines). Symmetry code: (i) x, −1 + y, z; (ii) 1 − x, −y, −z. Hydrogen atoms not involved in these interactions are omitted for clarity.

4. Database survey

A search of the Cambridge Structural Database (CSD version 5.40, last update May 2019; Groom et al., 2016 ) using (E)-3-phenyl-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one as the reference moiety resulted in three chalcone structures containing 2,4,6-trimethoxyphenyl with different substituents. They include (E)-3-(R₁)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one, where R₁ = 2,4,6-trimethoxyphenyl (BAGXEN; Kerr et al., 2001), 6-nitrobenzo[d][1,3]dioxol-5-yl (BUFMOF; Loghmani-Khouzani et al., 2009) and 4-methoxyphenyl (GESRAZ; Grealis et al., 2013). As in (I), the molecules of all these structures adopt a trans configuration with respect to C=C double bond (C6—C7—C8—C9 torsion angles = 175.5–179.1°). Although, τ₁ for all of the structures indicates an anti-periplanar conformation (Table 2), in BUFMOF it deviates slightly from planarity (τ₁ = 152.7°) whereas τ₁ for the other molecules is approximately 180° (τ₁ = 174.1–176.0°, Table 2). Regarding the enone bridge, the torsion angle τ₂ indicates that all of the structures are relatively planar (τ₂ = −4.8–7.6°). The torsion angles τ₃ always almost indicate a perpendicular arrangement (τ₃ = 67.6–88.6°). This might arise from the steric repulsion between the carbonyl group and the attached 2,4,6-trimethoxyphenyl ring. This results in an overall L-shape for all of the structures, with the dihedral angle between the mean planes of the two aromatic rings being 61.6–80.4°.

Table 2
Selected torsion and dihedral angles (°)

The dihedral angle is that between the mean planes of the aromatic rings.

Compound	R₁	τ₁ (C5—C6—C7—C8)	τ₂ (C7—C8—C9—C10)	τ₃ (C8—C9—C10—C11)	Dihedral angle
(I)	2-hydroxy-4-methylphenyl	−179.2 (1)	−0.8 (2)	76.9 (2)	75.8 (1)
BAGXEN	2,4,6-trimethoxyphenyl	174.1	−4.8	88.6	80.4
BUFMOF	6-nitrobenzo[d][1,3]dioxol-5-yl	153.7	6.8	67.6	61.6
GESRAZ	4-methoxyphenyl	176.0	7.6	−82.2	79.0
Note: values for the minor occupancy component of GESRAZ are not given.

5. Synthesis and crystallization

A reaction scheme for the synthesis of the title compound is given in Fig. 4. A solution of trimethoxyacetophenone (2 mmol) in 20 mL MeOH, LiOH (2.4 mmol) and 2-hydroxy-4-methylbenzaldehyde (1.6 mmol) was stirred at 368 K and the reaction progress was monitored by TLC. The reaction was quenched with diluted hydrochloric acid to pH = 6 and extracted with ethyl acetate. The organic layer was washed with aqueous NaHCO₃, water, and brine, successively. The organic layer was dried over anhydrous Na₂SO₄ and then concentrated to provide the product as a brown powder. The residue was purified by column chromatography with petroleum ether/ethyl acetate (10:1) as an eluent to afford the target compound (Yan et al., 2016 ). Slow evaporation from an acetonitrile–water mixture provided X-ray quality crystals for the target chalcone compound.

Figure 4
Reaction scheme for the synthesis of the title chalcone.

(E)-3-(2-hydroxy-4-methylphenyl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one (I)

Brown powder, yield 84.1%. m.p. 503–506 K. IR (cm⁻¹): 3283 (O—H), 2929 and 2842 (Csp³—H), 1603 (C=O), 1586 and 1457 (C=C). ¹H NMR (500 MHz, DMSO-d₆) δ, ppm: 10.02 (s, 1H), 7.45 (d, J = 16.2 Hz, 1H), 7.44 (d, J = 7.0 Hz, 1H), 6.86 (d, J = 16.2 Hz, 1H), 6.65 (d, J = 8.0 Hz, 2H), 6.30 (s, 2H), 3.83 (s, 3H), 3.70 (s, 6H), 2.23 (s, 3H). ¹³C-NMR (125 MHz, DMSO-d₆) δ, ppm: 194.3, 162.2, 158.4, 157.1, 142.5, 140.2, 128.8, 127.9, 121.1, 118.9, 117.0, 111.9, 91.6, 56.2, 55.9, 21.6. CHN Elemental analysis: Calculated for C₁₉H₂₀O₅: C, 69.50; H, 6.14; N. Found: C, 67.81; H, 5.72; N, 0.00.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. C-bound H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined using a riding model with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(C–methyl). The O-bound hydrogen was located from difference-Fourier maps and refined freely with O—H = 0.82 Å.

Table 3
Experimental details

Crystal data
Chemical formula	C₁₉H₂₀O₅
M_r	328.35
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	6.8072 (3), 8.5792 (4), 15.8010 (7)
α, β, γ (°)	100.365 (1), 99.433 (1), 104.984 (1)
V (Å³)	855.09 (7)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.57 × 0.25 × 0.21

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2012 )
T_min, T_max	0.908, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	33448, 5018, 3199
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.171, 1.05
No. of reflections	5018
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.19
Computer programs: APEX2 and SAINT (Bruker, 2012), SHELXS97 (Sheldrick, 2008 ), SHELXL2013 (Sheldrick, 2015 ), Mercury (Macrae et al., 2006 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1946810

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989019011289/jj2214sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019011289/jj2214Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989019011289/jj2214Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXL2013 (Sheldrick, 2015) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015) and PLATON (Spek, 2009).

(E)-3-(2-Hydroxy-4-methylphenyl)-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₉H₂₀O₅	Z = 2
M_r = 328.35	F(000) = 348
Triclinic, P1	D_x = 1.275 Mg m⁻³
a = 6.8072 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.5792 (4) Å	Cell parameters from 6606 reflections
c = 15.8010 (7) Å	θ = 2.5–25.7°
α = 100.365 (1)°	µ = 0.09 mm⁻¹
β = 99.433 (1)°	T = 296 K
γ = 104.984 (1)°	Block, brown
V = 855.09 (7) Å³	0.57 × 0.25 × 0.21 mm

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5018 independent reflections
Radiation source: fine-focus sealed tube	3199 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
φ and ω scans	θ_max = 30.1°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −9→9
T_min = 0.908, T_max = 0.950	k = −12→12
33448 measured reflections	l = −22→22

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.052	H-atom parameters constrained
wR(F²) = 0.171	w = 1/[σ²(F_o²) + (0.0776P)² + 0.1331P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
5018 reflections	Δρ_max = 0.27 e Å⁻³
217 parameters	Δρ_min = −0.19 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	0.64130 (18)	0.04792 (12)	0.33273 (7)	0.0582 (3)
H1B	0.622234	−0.051206	0.330607	0.087*
O2	0.5594 (2)	0.71937 (13)	0.28620 (9)	0.0750 (4)
O3	0.82818 (19)	0.58546 (15)	0.17162 (8)	0.0718 (4)
O4	0.3336 (2)	0.11733 (16)	−0.04471 (7)	0.0741 (4)
O5	0.18978 (18)	0.33623 (15)	0.22860 (8)	0.0653 (3)
C1	0.7621 (3)	0.3898 (2)	0.52362 (11)	0.0587 (4)
H1A	0.765072	0.500561	0.536913	0.070*
C2	0.8168 (3)	0.3175 (2)	0.59089 (11)	0.0636 (4)
H2A	0.856694	0.379893	0.648810	0.076*
C3	0.8134 (2)	0.1518 (2)	0.57349 (10)	0.0576 (4)
C4	0.7548 (2)	0.0621 (2)	0.48690 (10)	0.0536 (4)
H4A	0.752792	−0.048531	0.474238	0.064*
C5	0.6988 (2)	0.13422 (17)	0.41849 (9)	0.0462 (3)
C6	0.7017 (2)	0.30075 (17)	0.43524 (9)	0.0461 (3)
C7	0.6399 (2)	0.37021 (17)	0.36199 (9)	0.0462 (3)
H7A	0.600214	0.297697	0.306638	0.055*
C8	0.6322 (2)	0.52507 (17)	0.36314 (10)	0.0530 (4)
H8A	0.670606	0.601882	0.417082	0.064*
C9	0.5668 (2)	0.57758 (17)	0.28428 (10)	0.0506 (3)
C10	0.5066 (2)	0.45590 (17)	0.19626 (10)	0.0474 (3)
C11	0.3145 (2)	0.33383 (18)	0.16927 (10)	0.0496 (3)
C12	0.2590 (2)	0.2222 (2)	0.08827 (10)	0.0553 (4)
H12A	0.130137	0.141133	0.070877	0.066*
C13	0.3996 (3)	0.23348 (19)	0.03331 (10)	0.0539 (4)
C14	0.5911 (2)	0.35440 (19)	0.05781 (10)	0.0528 (4)
H14A	0.683280	0.361673	0.020255	0.063*
C15	0.6426 (2)	0.46422 (18)	0.13936 (10)	0.0502 (3)
C16	0.9764 (3)	0.6078 (3)	0.11824 (14)	0.0747 (5)
H16A	1.098130	0.697163	0.149806	0.112*
H16B	1.014327	0.507669	0.103655	0.112*
H16C	0.917128	0.633866	0.065061	0.112*
C17	0.4721 (4)	0.1217 (3)	−0.10396 (12)	0.0798 (6)
H17A	0.408006	0.034279	−0.156077	0.120*
H17B	0.501338	0.226820	−0.119882	0.120*
H17C	0.599756	0.106887	−0.075655	0.120*
C18	−0.0021 (3)	0.2085 (3)	0.21029 (14)	0.0741 (5)
H18A	−0.072792	0.225952	0.257352	0.111*
H18B	−0.087708	0.210054	0.155938	0.111*
H18C	0.024368	0.102923	0.205183	0.111*
C19	0.8715 (3)	0.0699 (3)	0.64692 (12)	0.0785 (6)
H19A	0.908022	0.148913	0.702583	0.118*
H19B	0.755129	−0.021899	0.646508	0.118*
H19C	0.988302	0.030616	0.638320	0.118*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0834 (8)	0.0397 (5)	0.0461 (6)	0.0191 (5)	0.0077 (5)	0.0007 (4)
O2	0.1156 (11)	0.0394 (6)	0.0798 (8)	0.0294 (6)	0.0388 (8)	0.0135 (5)
O3	0.0660 (7)	0.0665 (7)	0.0692 (8)	−0.0007 (6)	0.0305 (6)	−0.0029 (6)
O4	0.0803 (9)	0.0796 (8)	0.0461 (6)	0.0084 (7)	0.0123 (6)	−0.0022 (6)
O5	0.0577 (7)	0.0702 (7)	0.0659 (7)	0.0118 (5)	0.0271 (6)	0.0090 (6)
C1	0.0631 (9)	0.0534 (8)	0.0508 (8)	0.0140 (7)	0.0116 (7)	−0.0047 (7)
C2	0.0594 (9)	0.0766 (11)	0.0441 (8)	0.0141 (8)	0.0094 (7)	−0.0018 (7)
C3	0.0434 (8)	0.0790 (11)	0.0486 (8)	0.0153 (7)	0.0102 (6)	0.0146 (7)
C4	0.0527 (8)	0.0538 (8)	0.0543 (8)	0.0169 (7)	0.0119 (7)	0.0113 (7)
C5	0.0454 (7)	0.0463 (7)	0.0431 (7)	0.0118 (6)	0.0099 (6)	0.0030 (6)
C6	0.0432 (7)	0.0440 (7)	0.0464 (7)	0.0097 (5)	0.0117 (6)	0.0018 (6)
C7	0.0476 (7)	0.0406 (7)	0.0466 (7)	0.0112 (5)	0.0130 (6)	0.0009 (5)
C8	0.0607 (9)	0.0413 (7)	0.0523 (8)	0.0129 (6)	0.0163 (7)	−0.0009 (6)
C9	0.0586 (8)	0.0357 (6)	0.0600 (9)	0.0137 (6)	0.0246 (7)	0.0074 (6)
C10	0.0557 (8)	0.0403 (7)	0.0507 (8)	0.0185 (6)	0.0173 (6)	0.0108 (6)
C11	0.0525 (8)	0.0491 (8)	0.0530 (8)	0.0198 (6)	0.0169 (6)	0.0152 (6)
C12	0.0529 (8)	0.0563 (9)	0.0522 (8)	0.0117 (7)	0.0082 (7)	0.0113 (7)
C13	0.0638 (9)	0.0550 (8)	0.0426 (7)	0.0206 (7)	0.0073 (7)	0.0103 (6)
C14	0.0597 (9)	0.0568 (8)	0.0475 (8)	0.0214 (7)	0.0192 (7)	0.0136 (7)
C15	0.0539 (8)	0.0446 (7)	0.0543 (8)	0.0156 (6)	0.0169 (7)	0.0113 (6)
C16	0.0663 (11)	0.0762 (12)	0.0799 (13)	0.0099 (9)	0.0345 (10)	0.0137 (10)
C17	0.1025 (15)	0.0791 (12)	0.0497 (10)	0.0168 (11)	0.0256 (10)	0.0018 (8)
C18	0.0613 (10)	0.0826 (13)	0.0820 (13)	0.0132 (9)	0.0271 (9)	0.0297 (10)
C19	0.0684 (11)	0.1119 (16)	0.0570 (11)	0.0267 (11)	0.0087 (9)	0.0291 (10)

Geometric parameters (Å, º) top

O1—C5	1.3613 (16)	C8—H8A	0.9300
O1—H1B	0.8200	C9—C10	1.504 (2)
O2—C9	1.2255 (17)	C10—C15	1.390 (2)
O3—C15	1.3626 (19)	C10—C11	1.392 (2)
O3—C16	1.4151 (19)	C11—C12	1.383 (2)
O4—C13	1.3636 (18)	C12—C13	1.391 (2)
O4—C17	1.432 (2)	C12—H12A	0.9300
O5—C11	1.3651 (18)	C13—C14	1.385 (2)
O5—C18	1.419 (2)	C14—C15	1.384 (2)
C1—C2	1.371 (2)	C14—H14A	0.9300
C1—C6	1.403 (2)	C16—H16A	0.9600
C1—H1A	0.9300	C16—H16B	0.9600
C2—C3	1.392 (3)	C16—H16C	0.9600
C2—H2A	0.9300	C17—H17A	0.9600
C3—C4	1.381 (2)	C17—H17B	0.9600
C3—C19	1.511 (2)	C17—H17C	0.9600
C4—C5	1.387 (2)	C18—H18A	0.9600
C4—H4A	0.9300	C18—H18B	0.9600
C5—C6	1.3998 (19)	C18—H18C	0.9600
C6—C7	1.446 (2)	C19—H19A	0.9600
C7—C8	1.340 (2)	C19—H19B	0.9600
C7—H7A	0.9300	C19—H19C	0.9600
C8—C9	1.441 (2)

C5—O1—H1B	109.5	C11—C12—C13	118.68 (15)
C15—O3—C16	119.21 (13)	C11—C12—H12A	120.7
C13—O4—C17	117.54 (14)	C13—C12—H12A	120.7
C11—O5—C18	118.63 (14)	O4—C13—C14	123.74 (14)
C2—C1—C6	121.65 (15)	O4—C13—C12	114.86 (14)
C2—C1—H1A	119.2	C14—C13—C12	121.39 (14)
C6—C1—H1A	119.2	C15—C14—C13	118.62 (14)
C1—C2—C3	120.75 (15)	C15—C14—H14A	120.7
C1—C2—H2A	119.6	C13—C14—H14A	120.7
C3—C2—H2A	119.6	O3—C15—C14	123.97 (13)
C4—C3—C2	118.51 (15)	O3—C15—C10	114.45 (13)
C4—C3—C19	120.07 (17)	C14—C15—C10	121.57 (14)
C2—C3—C19	121.41 (16)	O3—C16—H16A	109.5
C3—C4—C5	121.08 (15)	O3—C16—H16B	109.5
C3—C4—H4A	119.5	H16A—C16—H16B	109.5
C5—C4—H4A	119.5	O3—C16—H16C	109.5
O1—C5—C4	121.92 (13)	H16A—C16—H16C	109.5
O1—C5—C6	117.19 (12)	H16B—C16—H16C	109.5
C4—C5—C6	120.89 (13)	O4—C17—H17A	109.5
C5—C6—C1	117.12 (14)	O4—C17—H17B	109.5
C5—C6—C7	118.98 (12)	H17A—C17—H17B	109.5
C1—C6—C7	123.89 (13)	O4—C17—H17C	109.5
C8—C7—C6	128.71 (13)	H17A—C17—H17C	109.5
C8—C7—H7A	115.6	H17B—C17—H17C	109.5
C6—C7—H7A	115.6	O5—C18—H18A	109.5
C7—C8—C9	122.77 (13)	O5—C18—H18B	109.5
C7—C8—H8A	118.6	H18A—C18—H18B	109.5
C9—C8—H8A	118.6	O5—C18—H18C	109.5
O2—C9—C8	122.17 (14)	H18A—C18—H18C	109.5
O2—C9—C10	118.36 (14)	H18B—C18—H18C	109.5
C8—C9—C10	119.47 (12)	C3—C19—H19A	109.5
C15—C10—C11	118.35 (13)	C3—C19—H19B	109.5
C15—C10—C9	120.27 (13)	H19A—C19—H19B	109.5
C11—C10—C9	121.37 (13)	C3—C19—H19C	109.5
O5—C11—C12	124.18 (14)	H19A—C19—H19C	109.5
O5—C11—C10	114.43 (13)	H19B—C19—H19C	109.5
C12—C11—C10	121.39 (14)

C6—C1—C2—C3	−0.3 (3)	C18—O5—C11—C12	5.6 (2)
C1—C2—C3—C4	0.4 (2)	C18—O5—C11—C10	−174.96 (14)
C1—C2—C3—C19	−179.49 (16)	C15—C10—C11—O5	−179.09 (12)
C2—C3—C4—C5	−0.5 (2)	C9—C10—C11—O5	0.4 (2)
C19—C3—C4—C5	179.37 (14)	C15—C10—C11—C12	0.4 (2)
C3—C4—C5—O1	179.78 (14)	C9—C10—C11—C12	179.85 (13)
C3—C4—C5—C6	0.5 (2)	O5—C11—C12—C13	179.48 (13)
O1—C5—C6—C1	−179.66 (13)	C10—C11—C12—C13	0.1 (2)
C4—C5—C6—C1	−0.3 (2)	C17—O4—C13—C14	0.2 (2)
O1—C5—C6—C7	1.36 (19)	C17—O4—C13—C12	−179.57 (15)
C4—C5—C6—C7	−179.32 (13)	C11—C12—C13—O4	179.14 (13)
C2—C1—C6—C5	0.2 (2)	C11—C12—C13—C14	−0.6 (2)
C2—C1—C6—C7	179.15 (14)	O4—C13—C14—C15	−178.99 (14)
C5—C6—C7—C8	−179.68 (14)	C12—C13—C14—C15	0.8 (2)
C1—C6—C7—C8	1.4 (2)	C16—O3—C15—C14	3.0 (2)
C6—C7—C8—C9	−179.96 (14)	C16—O3—C15—C10	−178.38 (15)
C7—C8—C9—O2	179.67 (15)	C13—C14—C15—O3	178.26 (14)
C7—C8—C9—C10	−0.8 (2)	C13—C14—C15—C10	−0.3 (2)
O2—C9—C10—C15	75.90 (19)	C11—C10—C15—O3	−178.96 (13)
C8—C9—C10—C15	−103.68 (16)	C9—C10—C15—O3	1.6 (2)
O2—C9—C10—C11	−103.56 (17)	C11—C10—C15—C14	−0.3 (2)
C8—C9—C10—C11	76.87 (19)	C9—C10—C15—C14	−179.73 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O2ⁱ	0.82	1.88	2.6653 (15)	161
C17—H17A···O1ⁱⁱ	0.96	2.70	3.520 (2)	144

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

Selected torsion and dihedral angles (°) top

The dihedral angle is that between the mean planes of the aromatic rings.

Compound	R₁	τ₁ (C5—C6—C7—C8)	τ₂ (C7—C8—C9—C10)	τ₃ (C8—C9—C10—C11)	Dihedral angle
(I)	2-hydroxy-4-methylphenyl	-179.2 (1)	-0.8 (2)	76.9 (2)	75.8 (1)
BAGXEN	2,4,6-trimethoxyphenyl	174.1	-4.8	88.6	80.4
BUFMOF	6-nitrobenzo[d][1,3]dioxol-5-yl	153.7	6.8	67.6	61.6
GESRAZ	4-methoxyphenyl	176.0	7.6	-82.2	79.0

Note: values for the minor occupancy component of GESRAZ are not given.

Funding information

The authors would like to express their sincere gratitude to Universiti Sains Malaysia for the financial support from the Bridging Research Grant 2017 (304.PKIMIA.6316171).

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