The synthesis, crystal structure and spectroscopic analysis of (E)-3-(4-chloro­phen­yl)-1-(2,3-di­hydro­benzo[b][1,4]dioxin-6-yl)prop-2-en-1-one

Vinaya; Richard, A.S.; Murthy, S.M.; Basavaraju, Y.B.; Yathirajan, H.S.; Parkin, S.

doi:10.1107/S2056989023005613

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ISSN: 2056-9890

Volume 79| Part 7| July 2023| Pages 674-677

https://doi.org/10.1107/S2056989023005613

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The synthesis, crystal structure and spectroscopic analysis of (E)-3-(4-chlorophenyl)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)prop-2-en-1-one

Vinaya,^a Austin S. Richard,^b Subbiah M. Murthy,^c Yeriyur B. Basavaraju,^a ^* Hemmige S. Yathirajan ^a ^* and Sean Parkin ^d

^aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India, ^bAavishkaar Research Centre, Coorg Institute of Dental Sciences, Virajpet 571 218, India, ^cDepartment of Microbiology, Yuvaraja's College, Mysore 570 005, India, and ^dDepartment of Chemistry, University of Kentucky, Lexington, KY 40506-0055, USA
^*Correspondence e-mail: ybb2706@gmail.com, yathirajan@hotmail.com

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 20 June 2023; accepted 26 June 2023; online 30 June 2023)

The synthesis, crystal structure and spectroscopic analysis of (E)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(4-chlorophenyl)prop-2-en-1-one (C₁₇H₁₃ClO₃), a substituted chalcone, are described. The overall geometry of the molecule is largely planar (r.m.s. deviation = 0.1742 Å), but slightly kinked, leading to a dihedral angle between the planes of the benzene rings at either side of the molecule of 8.31 (9)°. In the crystal, only weak interactions determine the packing motifs. These include C—H⋯O and C—H⋯Cl hydrogen bonds and π–π overlap of aromatic rings.

Keywords: crystal structure; chalcone; π–π interaction.

CCDC reference: 2272334

1. Chemical context

Chalcones exhibit a wide range of fascinating biological and pharmacological properties. Some of their beneficial attributes include anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic and anticancer activities (Dimmock et al., 1999 ). Moreover, several chalcones have demonstrated significant antimalarial properties (Troeberg et al., 2000 ). The efficient second-harmonic generation (SHG) conversion efficiency of some chalcones has also made them promising organic nonlinear optical (NLO) materials (Sarojini et al., 2006 ). The presence of phenolic groups in many chalcones has garnered attention due to their radical quenching capabilities, making these compounds and chalcone-rich plant extracts potential candidates for drug development or food preservation (Dhar et al., 1981 ; Di Carlo et al., 1999 ). The design, synthesis and evaluation of 1,4-benzodioxane-substituted chalcones as selective and reversible inhibitors of human monoamine oxidase B was reported by Kong et al. (2020 ). Furthermore, Shinde et al. (2020 ) have conducted experimental and theoretical studies on the molecular structure, FT–IR, NMR, HOMO/LUMO frontier orbital, molecular electrostatic potential (MESP) and reactivity descriptors of (E)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one. They have also reported the synthesis, antibacterial and computational studies of halo-chalcone hybrids derived from 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethan-1-one (Shinde et al., 2021 ) and of two trifluorinated chalcones derived from 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethan-1-one (Shinde et al., 2022a ), as well as investigations of (E)-4-(3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-oxoprop-1-en-1-yl)benzonitrile (Shinde et al., 2022b ). Additionally, Zhuang et al. (2017 ) presented a comprehensive review on the chalcone framework as a privileged structure in medicinal chemistry, while Elkanzi et al. (2022 ) have published a review on the synthesis of chalcone derivatives and their biological activities.

Given the general significance of chalcones, we report herein the synthesis of (E)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(4-chlorophenyl)prop-2-en-1-one, C₁₇H₁₃ClO₃ (I), along with its crystal structure and related studies.

2. Structural commentary

As shown in Fig. 1, the overall conformation of the molecule of I is determined by the torsion angles C3—C2—C1—C10 [169.9 (2)°], C2—C1—C10—C11 [−171.3 (3)°], C1—C10—C11—C12 [−179.0 (3)°] and C10—C11—C12—C17 [−176.7 (3)°] of the propenone moiety. In magnitude, these are all within about 10° of 180°, which makes the molecule largely flat (r.m.s. deviation for the non-H atoms is 0.1742 Å), though slightly bent, leading to a dihedral angle between the chlorophenyl and dihydrobenzodioxine rings of 8.31 (9)°. The conformation of the dihydrodioxine ring, as determined by its Cremer–Pople puckering parameters (Cremer & Pople, 1975 ) [Q = 0.466 (3) Å, θ = 51.2 (4)° and φ = 282.6 (4)°], is closest to half-chair (Boeyens, 1978 ). This puckering places atoms C5 and C6 at 0.499 (4) and −0.207 (4) Å on either side of the mean plane of the dihydrobenzodioxine ring. All bond lengths and angles lie within the typical ranges found in organic structures.

Figure 1
The molecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level.

3. Supramolecular features

The crystal packing in I is governed solely by weak interactions, as the only possible hydrogen-bond donors are of type C—H. The absence of any sharp spikes protruding to the lower left in the Hirshfeld surface fingerprint plots (Fig. 2) calculated using CrystalExplorer (Spackman et al., 2021 ) clearly marks the absence of any very close contacts. Indeed, only two such contacts are flagged as intermolecular hydrogen-bond-type interactions by the default SHELXL HTAB command. These are C5—H5A⋯O3ⁱ and C5—H5B⋯Clⁱⁱ [symmetry codes: (i) x − $[{1\over 2}]$ , −y + $[{3\over 2}]$ , z; (ii) x − 1, y, z − 1], shown in Table 1. The benzene rings of the 4-chlorophenyl and dihydrobenzodioxine groups, however, exhibit π–π overlap, which link the molecules into chains that extend parallel to [001], as shown in Fig. 3. The centroid–centroid distances [3.747 (18) Å] and the dihedral angle between the participating rings [6.12 (11)°] imply that these are rather weak interactions.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O3ⁱ	0.99	2.61	3.595 (4)	172
C5—H5B⋯Cl1ⁱⁱ	0.99	2.80	3.455 (3)	124
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (ii) .

Figure 2
Hirshfeld surface fingerprint plots showing (a) H⋯H contacts = 30.4% coverage, (b) H⋯C = 26.8%, (c) H⋯O = 20.6% and (d) H⋯Cl = 12.7%. Reciprocal contacts are included in the coverage fractions. Other contact types were unremarkable.

Figure 3
A partial packing plot of I, viewed approximately down the a axis. The stacking of the aromatic rings is shown by dotted lines between ring centroids, which lead to chains of molecules that extend parallel to [001].

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.43 with updates to November 2022; Groom et al., 2016 ) using a molecular fragment consisting of chalcone (C₆H₅C=OCH=CHC₆H₅) with no specific substituents returned 4725 hits. With hydrogen attached across the C=C double bond, the search gave 1200 hits. Of these entries, 155 had `any halogen' at the equivalent of C15 in I, 62 of which had Cl. A search fragment without the halogen but with `any oxygen bound' substituent at the equivalent of C4 and C7 produced 78 matches. Addition of the aforementioned halogen reduced this to 14 structures, seven of which were chlorides, but only five are unique. These are: BOJFIQ [(2E)-1-(1,3-benzodioxol-5-yl)-3-(4-chlorophenyl)prop-2-en-1-one; Jasinski et al., 2008 ], FATFIR [(E)-3-(2,4-dichlorophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one; Wu et al., 2012 ], TICDIT [3-(4-chlorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one; Teh et al., 2007 ], VIDDIW [3-(2,4-dichlorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one; Ng et al., 2007 ] and XOLLOC [3-(4-chloro-3-fluorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one; Çelikesir et al., 2019 ]. A few other related chalcone structures include: QERYOC [(2E)-3-(1,3-benzodioxol-5-yl)-1-(4-bromophenyl)prop-2-en-1-one; Harrison et al., 2006 ], KUYWOR [(2E)-3-(1,3-benzodioxol-5-yl)-1-(3-bromo-2-thienyl)prop-2-en-1-one; Harrison et al., 2010 ], TUNTAY [(2E)-1-(1,3-benzodioxol-5-yl)-3-(2-bromophenyl)prop-2-en-1-one; Li et al., 2010 ], and UNUZUZ {(E)-3-(8-benzyloxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]prop-2-en-1-one; Zhang et al., 2011 }.

5. Synthesis, crystallization, and spectroscopic data

1-(2,3-Dihydrobenzo[1,4]dioxin-6-yl)ethanone was prepared by Friedel–Crafts acylation of benzo[1,4]dioxane using ether as solvent (Fig. 4). 1-(2,3-Dihydrobenzo[1,4]dioxin-6-yl)ethanone (1.78 g, 0.01 mol) and 4-chlorobenzaldehyde (1.40 g, 0.01 mol) were stirred in a 30% ethanolic NaOH and water mixture at 293 K for 4–6 h. The reaction mixture was refrigerated overnight. The precipitate that formed was filtered off and dried. X-ray-quality crystals were obtained from a solvent mixture of DMF–DMSO (dimethylformamide–dimethyl sulfoxide) (1:1 v/v) and the corresponding melting point was found to be 410–411 K.

Figure 4
A generalized reaction scheme for the synthesis of I.

FT–IR (ν in cm⁻¹): 3156–2934 (Ar-CH), 1655 (C=O), 1575 (C=C); ¹H NMR (CDCl₃, 400 MHz): δ 7.71 (d, 1H, β-CH), 7.92 (d, 2H, Ar-H), 7.62 (d, 2H, Ar-H), 7.23 (d, 1H, 2,3-dihydrobenzo[1,4]dioxine Ar-H), 7.21 (d, 1H, 2,3-dihydrobenzo[1,4]dioxine Ar-H), 7.01 (d, 1H, α-CH), 6.93 (s, 1H, 2,3-dihydrobenzo[1,4]dioxine Ar-H), 4.14 (m, 4H, 1,4-dioxane CH₂); ¹³C NMR (CDCl₃, 100 MHz): δ 196.1, 156.5, 149.8, 145.1, 133.5, 133.3, 129.0, 128.7, 122.1, 121.4, 121.3, 112.0, 106.8, 64.2.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were found in difference Fourier maps and subsequently included in the refinement using riding models, with constrained distances set to 0.95 [C(sp²)H] and 0.99 Å (R₂CH₂). U_iso(H) values were set to 1.2U_eq of the attached atom. The absolute structure was determined using 1035 quotients of the form [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013 ).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₃ClO₃
M_r	300.72
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	200
a, b, c (Å)	5.8655 (5), 14.3499 (17), 16.4803 (19)
V (Å³)	1387.1 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.28
Crystal size (mm)	0.26 × 0.23 × 0.22

Data collection
Diffractometer	Bruker D8 Venture dual source
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.788, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	17057, 2896, 2694
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.083, 1.07
No. of reflections	2896
No. of parameters	190
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.16
Absolute structure	Flack x determined using 1035 quotients [(I⁺) − (I⁻)]/[(I⁺) + (I⁻)] (Parsons et al., 2013)
Absolute structure parameter	0.01 (2)
Computer programs: APEX3 (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL2019 (Sheldrick, 2015b ), Mercury (Macrae et al., 2020 ), SHELX (Sheldrick, 2008 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2272334

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989023005613/vm2285sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023005613/vm2285Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: APEX3 (Bruker, 2016); data reduction: APEX3 (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELX (Sheldrick, 2008) and publCIF (Westrip, 2010).

(E)-3-(4-Chlorophenyl)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)prop-2-en-1-one top

Crystal data top

C₁₇H₁₃ClO₃	D_x = 1.440 Mg m⁻³
M_r = 300.72	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 9943 reflections
a = 5.8655 (5) Å	θ = 2.5–27.6°
b = 14.3499 (17) Å	µ = 0.28 mm⁻¹
c = 16.4803 (19) Å	T = 200 K
V = 1387.1 (3) Å³	Cut block, pale yellow
Z = 4	0.26 × 0.23 × 0.22 mm
F(000) = 624

Data collection top

Bruker D8 Venture dual source diffractometer	2896 independent reflections
Radiation source: microsource	2694 reflections with I > 2σ(I)
Detector resolution: 7.41 pixels mm^-1	R_int = 0.038
φ and ω scans	θ_max = 27.6°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −7→7
T_min = 0.788, T_max = 0.971	k = −18→18
17057 measured reflections	l = −19→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.083	w = 1/[σ²(F_o²) + (0.0322P)² + 0.4666P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2896 reflections	Δρ_max = 0.21 e Å⁻³
190 parameters	Δρ_min = −0.16 e Å⁻³
1 restraint	Absolute structure: Flack x determined using 1035 quotients [(I+)-(I-)]/[(I+)+(I-)] [Parsons et al. (2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (2)

Special details top

Experimental. The crystal was mounted using polyisobutene oil on the tip of a fine glass fibre, which was fastened in a copper mounting pin with electrical solder. It was placed directly into the cold gas stream of a liquid-nitrogen based cryostat (Hope, 1994; Parkin & Hope, 1998).

The crystals appeared to undergo a destructive phase transition when cooled to 90K. Visual inspection of crystal integrity and diffraction quality vs temperature established a safe temperature for data collection of -73° C.

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. Refinement progress was checked using Platon (Spek, 2020) and by an R-tensor (Parkin, 2000). The final model was further checked with the IUCr utility checkCIF.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.86056 (16)	0.65710 (6)	0.91506 (5)	0.0577 (3)
O1	−0.0096 (3)	0.59370 (18)	0.48876 (12)	0.0505 (6)
O2	0.0030 (3)	0.57318 (14)	0.18914 (12)	0.0416 (5)
O3	0.4399 (4)	0.64129 (16)	0.14256 (12)	0.0443 (5)
C1	0.1903 (5)	0.6112 (2)	0.47247 (15)	0.0338 (6)
C2	0.2634 (4)	0.61897 (18)	0.38646 (15)	0.0286 (5)
C3	0.1080 (4)	0.59307 (18)	0.32641 (17)	0.0318 (5)
H3	−0.038161	0.570520	0.341626	0.038*
C4	0.1637 (4)	0.59976 (17)	0.24503 (16)	0.0300 (5)
C5	0.0414 (6)	0.6143 (2)	0.11107 (17)	0.0453 (7)
H5A	0.008461	0.681919	0.113519	0.054*
H5B	−0.062554	0.585853	0.070731	0.054*
C6	0.2829 (6)	0.5995 (2)	0.08557 (18)	0.0475 (8)
H6A	0.313824	0.531780	0.081738	0.057*
H6B	0.306758	0.627076	0.031178	0.057*
C7	0.3778 (5)	0.63300 (19)	0.22209 (16)	0.0320 (6)
C8	0.5313 (5)	0.66010 (18)	0.28102 (18)	0.0343 (6)
H8	0.675979	0.683954	0.265581	0.041*
C9	0.4761 (5)	0.65280 (18)	0.36243 (17)	0.0329 (6)
H9	0.584046	0.671004	0.402365	0.040*
C10	0.3628 (5)	0.62304 (19)	0.53720 (16)	0.0361 (6)
H10	0.511960	0.643759	0.523877	0.043*
C11	0.3090 (5)	0.60465 (18)	0.61436 (15)	0.0314 (6)
H11	0.158246	0.583195	0.624038	0.038*
C12	0.4563 (4)	0.61380 (17)	0.68570 (15)	0.0297 (5)
C13	0.6738 (4)	0.65334 (18)	0.68259 (17)	0.0326 (5)
H13	0.737075	0.671519	0.631943	0.039*
C14	0.7979 (5)	0.66609 (18)	0.75398 (18)	0.0347 (6)
H14	0.945533	0.693264	0.752293	0.042*
C15	0.7047 (5)	0.63898 (18)	0.82670 (18)	0.0355 (6)
C16	0.4927 (5)	0.59816 (19)	0.83158 (18)	0.0367 (6)
H16	0.432553	0.578743	0.882366	0.044*
C17	0.3696 (5)	0.58612 (18)	0.76102 (16)	0.0330 (6)
H17	0.222733	0.558409	0.763644	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0663 (5)	0.0745 (5)	0.0324 (4)	−0.0046 (4)	−0.0248 (4)	0.0048 (4)
O1	0.0324 (10)	0.0939 (18)	0.0252 (10)	−0.0057 (11)	0.0000 (9)	0.0001 (10)
O2	0.0414 (11)	0.0586 (12)	0.0248 (9)	−0.0105 (10)	−0.0082 (9)	0.0018 (9)
O3	0.0440 (11)	0.0634 (14)	0.0254 (10)	−0.0025 (10)	0.0040 (9)	0.0059 (9)
C1	0.0345 (14)	0.0442 (15)	0.0226 (13)	0.0005 (12)	−0.0028 (11)	−0.0017 (12)
C2	0.0283 (12)	0.0340 (13)	0.0234 (12)	0.0011 (10)	−0.001 (1)	0.0006 (10)
C3	0.0312 (12)	0.0381 (13)	0.0261 (13)	−0.0009 (10)	−0.0011 (11)	0.0015 (11)
C4	0.0313 (13)	0.0327 (12)	0.0259 (12)	−0.0001 (11)	−0.0058 (11)	0.0007 (10)
C5	0.0526 (18)	0.0612 (18)	0.0221 (13)	−0.0025 (15)	−0.0101 (13)	0.0041 (13)
C6	0.0591 (19)	0.062 (2)	0.0217 (13)	0.0047 (16)	−0.0007 (14)	−0.0005 (13)
C7	0.0326 (14)	0.0374 (13)	0.0259 (13)	0.0032 (11)	0.0014 (11)	0.004 (1)
C8	0.0288 (13)	0.0410 (14)	0.0330 (14)	−0.0026 (11)	0.0014 (12)	0.0034 (12)
C9	0.0303 (12)	0.0380 (14)	0.0305 (13)	−0.0033 (10)	−0.0059 (11)	−0.0012 (11)
C10	0.0326 (13)	0.0489 (16)	0.0268 (14)	−0.0015 (13)	−0.0020 (11)	−0.0015 (13)
C11	0.0291 (13)	0.0403 (14)	0.0247 (13)	−0.0004 (11)	−0.0012 (10)	−0.0031 (11)
C12	0.0316 (13)	0.0330 (13)	0.0246 (13)	0.0023 (10)	0.0005 (11)	−0.0017 (11)
C13	0.0324 (13)	0.0396 (13)	0.0259 (13)	−0.0005 (10)	−0.0024 (11)	0.0010 (11)
C14	0.0321 (13)	0.0387 (14)	0.0332 (14)	0.0003 (11)	−0.0069 (12)	0.0010 (12)
C15	0.0416 (15)	0.0393 (13)	0.0255 (12)	0.0060 (11)	−0.0117 (12)	0.0000 (11)
C16	0.0430 (15)	0.0416 (14)	0.0256 (13)	0.0023 (12)	−0.0005 (12)	0.0033 (12)
C17	0.0337 (13)	0.0362 (13)	0.0292 (14)	−0.0005 (10)	0.0021 (11)	0.0013 (11)

Geometric parameters (Å, º) top

Cl1—C15	1.739 (3)	C7—C8	1.380 (4)
O1—C1	1.229 (3)	C8—C9	1.384 (4)
O2—C4	1.372 (3)	C8—H8	0.9500
O2—C5	1.433 (3)	C9—H9	0.9500
O3—C7	1.366 (3)	C10—C11	1.336 (4)
O3—C6	1.446 (4)	C10—H10	0.9500
C1—C10	1.480 (4)	C11—C12	1.465 (4)
C1—C2	1.485 (3)	C11—H11	0.9500
C2—C3	1.396 (4)	C12—C13	1.397 (4)
C2—C9	1.396 (4)	C12—C17	1.399 (4)
C3—C4	1.384 (4)	C13—C14	1.396 (4)
C3—H3	0.9500	C13—H13	0.9500
C4—C7	1.395 (4)	C14—C15	1.373 (4)
C5—C6	1.493 (5)	C14—H14	0.9500
C5—H5A	0.9900	C15—C16	1.377 (4)
C5—H5B	0.9900	C16—C17	1.379 (4)
C6—H6A	0.9900	C16—H16	0.9500
C6—H6B	0.9900	C17—H17	0.9500

C4—O2—C5	112.4 (2)	C7—C8—H8	119.7
C7—O3—C6	114.7 (2)	C9—C8—H8	119.7
O1—C1—C10	121.2 (2)	C8—C9—C2	120.7 (2)
O1—C1—C2	120.0 (2)	C8—C9—H9	119.7
C10—C1—C2	118.8 (2)	C2—C9—H9	119.7
C3—C2—C9	118.4 (2)	C11—C10—C1	120.1 (3)
C3—C2—C1	117.9 (2)	C11—C10—H10	119.9
C9—C2—C1	123.7 (2)	C1—C10—H10	119.9
C4—C3—C2	121.0 (2)	C10—C11—C12	127.4 (3)
C4—C3—H3	119.5	C10—C11—H11	116.3
C2—C3—H3	119.5	C12—C11—H11	116.3
O2—C4—C3	118.0 (2)	C13—C12—C17	118.7 (2)
O2—C4—C7	122.1 (3)	C13—C12—C11	123.0 (2)
C3—C4—C7	119.9 (2)	C17—C12—C11	118.2 (2)
O2—C5—C6	110.0 (3)	C14—C13—C12	119.9 (3)
O2—C5—H5A	109.7	C14—C13—H13	120.0
C6—C5—H5A	109.7	C12—C13—H13	120.0
O2—C5—H5B	109.7	C15—C14—C13	119.4 (3)
C6—C5—H5B	109.7	C15—C14—H14	120.3
H5A—C5—H5B	108.2	C13—C14—H14	120.3
O3—C6—C5	111.2 (2)	C14—C15—C16	122.1 (3)
O3—C6—H6A	109.4	C14—C15—Cl1	118.6 (2)
C5—C6—H6A	109.4	C16—C15—Cl1	119.3 (2)
O3—C6—H6B	109.4	C15—C16—C17	118.5 (3)
C5—C6—H6B	109.4	C15—C16—H16	120.8
H6A—C6—H6B	108.0	C17—C16—H16	120.8
O3—C7—C8	118.5 (3)	C16—C17—C12	121.5 (3)
O3—C7—C4	122.0 (3)	C16—C17—H17	119.3
C8—C7—C4	119.5 (3)	C12—C17—H17	119.3
C7—C8—C9	120.5 (2)

O1—C1—C2—C3	−8.9 (4)	C4—C7—C8—C9	1.3 (4)
C10—C1—C2—C3	169.9 (2)	C7—C8—C9—C2	−0.8 (4)
O1—C1—C2—C9	169.5 (3)	C3—C2—C9—C8	−0.2 (4)
C10—C1—C2—C9	−11.7 (4)	C1—C2—C9—C8	−178.6 (3)
C9—C2—C3—C4	0.7 (4)	O1—C1—C10—C11	7.4 (4)
C1—C2—C3—C4	179.1 (2)	C2—C1—C10—C11	−171.3 (3)
C5—O2—C4—C3	158.0 (3)	C1—C10—C11—C12	−179.0 (2)
C5—O2—C4—C7	−21.8 (4)	C10—C11—C12—C13	6.8 (4)
C2—C3—C4—O2	−180.0 (2)	C10—C11—C12—C17	−176.7 (3)
C2—C3—C4—C7	−0.1 (4)	C17—C12—C13—C14	−1.2 (4)
C4—O2—C5—C6	50.4 (3)	C11—C12—C13—C14	175.3 (2)
C7—O3—C6—C5	38.6 (4)	C12—C13—C14—C15	0.4 (4)
O2—C5—C6—O3	−60.1 (4)	C13—C14—C15—C16	0.9 (4)
C6—O3—C7—C8	171.8 (3)	C13—C14—C15—Cl1	−179.0 (2)
C6—O3—C7—C4	−9.4 (4)	C14—C15—C16—C17	−1.3 (4)
O2—C4—C7—O3	0.2 (4)	Cl1—C15—C16—C17	178.7 (2)
C3—C4—C7—O3	−179.6 (3)	C15—C16—C17—C12	0.4 (4)
O2—C4—C7—C8	179.0 (2)	C13—C12—C17—C16	0.8 (4)
C3—C4—C7—C8	−0.8 (4)	C11—C12—C17—C16	−175.8 (2)
O3—C7—C8—C9	−179.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O3ⁱ	0.99	2.61	3.595 (4)	172
C5—H5B···Cl1ⁱⁱ	0.99	2.80	3.455 (3)	124

Symmetry codes: (i) x−1/2, −y+3/2, z; (ii) x−1, y, z−1.

Acknowledgements

One of the authors (V) is grateful to the DST–PURSE Project, Vijnana Bhavana, UOM for providing research facilities. HSY thanks UGC for a BSR Faculty fellowship for three years.

Funding information

Funding for this research was provided by: NSF (MRI CHE1625732) and the University of Kentucky (Bruker D8 Venture diffractometer) to SP.

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