Crystal structure and Hirshfeld-surface analysis of 1-(4-fluoro­phen­yl)-3,3-bis­(methyl­sulfan­yl)prop-2-en-1-one

Mohan Kumar, T.M.; Bhaskar, B.L.; Bhavya, P.; Divakara, T.R.; Shankara Prasad, H.J.; Yathirajan, H.S.; Parkin, S.

doi:10.1107/S2056989025004189

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Volume 81| Part 6| June 2025|

https://doi.org/10.1107/S2056989025004189

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Crystal structure and Hirshfeld-surface analysis of 1-(4-fluorophenyl)-3,3-bis(methylsulfanyl)prop-2-en-1-one

Thaluru M. Mohan Kumar,^a Besagarahally L. Bhaskar,^a Papegowda Bhavya,^b Thayamma R. Divakara,^c Holehundi J. Shankara Prasad,^d Hemmige S. Yathirajan ^e ^* and Sean Parkin ^f

^aDepartment of Physical Sciences, Amrita School of Engineering, Amrita Vishwa Vidyapeetham, Bengaluru-560 035, India, ^bDepartment of Applied Sciences, New Horizon College of Engineering, Bengaluru-560 103, India, ^cDepartment of Chemistry, T. John Institute of Technology, Bengaluru-560 083, India, ^dDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysore-570 005, India, ^eDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, India, and ^fDepartment of Chemistry, University of Kentucky, Lexington, KY, 40506-0055, USA
^*Correspondence e-mail: yathirajan@hotmail.com

Edited by X. Hao, Institute of Chemistry, Chinese Academy of Sciences (Received 1 May 2025; accepted 8 May 2025; online 13 May 2025)

The title compound, C₁₁H₁₁FOS₂, is a fluorinated chalcone derivative with potential applications in medicinal chemistry and functional materials. The molecular structure includes a planar 4-fluorophenyl ring linked by a carbonyl group and an ethenyl spacer to an approximately planar bis(methylsulfanyl) moiety (r.m.s. deviations from planarity are 0.0106 and 0.0315 Å, respectively). These planar groups are twisted relative to each other, subtending a dihedral angle of 32.23 (4)°. The crystal packing lacks classical hydrogen bonds or aromatic π-stacking, but molecules are connected through weaker C—H⋯O and C—H⋯S contacts into layers parallel to the ab plane and tapes extending along the b-axis direction. The 4-fluorophenyl groups on adjacent tapes interdigitate. Hirshfeld surface analysis shows that the majority (>90%) of intermolecular contacts involve hydrogen atoms.

Keywords: crystal structure; Hirshfeld-surface analysis; chalcone derivative.

CCDC reference: 2449698

1. Chemical context

1-(4-Fluorophenyl)-3,3-bis(methylsulfanyl)prop-2-en-1-one (I) is a fluorinated chalcone derivative with potential applications in medicinal and functional materials chemistry. Natural and synthetic chalcones have been widely utilized for their broad spectrum of biological activities, which include anti-microbial, anti-cancer, anti-diabetic, anti-inflammatory, anti-oxidant, anti-parasitic, and neuroprotective effects (Lin et al., 2002 ; Bhat et al., 2005 ; Trivedi et al., 2007 ; Lahtchev et al., 2008 ; Aneja et al., 2018 ). The presence of fluorine may enhance interactions with biological systems, potentially inhibiting enzyme activity or receptors involved in disease processes. In this context, fluorinated chalcone derivatives have shown notable bioactivity (Nakamura et al., 2002 ). The significance of the chalcone scaffold in medicinal chemistry is well established, having been identified as a ‘privileged structure' with considerable therapeutic potential (Zhuang et al., 2017 ). Several reviews have explored the synthesis, structural diversity, and biological relevance of chalcones and their derivatives, including their roles as anti-infective agents and enzyme inhibitors (Nowakowska, 2007 ; Elkanzi et al., 2022 ; de Mello et al., 2018 ; Opletalova & Sedivy, 1999 ). The methylsulfanyl groups also contribute to its chemical reactivity (Nakamura et al., 2002), suggesting this class of compounds as promising candidates in the development of advanced functional materials. Examples include applications in optical data storage systems (Corredor et al., 2007 ), electronics and coatings (Belahlou et al., 2020 ) as well as non-linear optical (NLO) materials (Xu et al., 2020 ).

In light of the importance of chalcones and their derivatives in several areas of chemistry, physics, medicine, pharmaceuticals and biology, this paper reports the crystal structure and a Hirshfeld-surface analysis of I.

2. Structural commentary

The molecular structure of I consists of a 4-fluorophenyl ring bonded to a carbonyl group, which in turn is attached via an ethenyl linker to a bis(methylsulfanyl) moiety, as shown in Fig. 1. All bond lengths and angles in I fall within normal ranges. The overall geometry is essentially that of two planar groups twisted with respect to each other about the C4—C7 bond [torsion C5—C4—C7—O1 = −28.68 (16)°], with a smaller twist about the C7—C8 bond [O1—C7—C8—C9 = 4.91 (18)°]. These two planar moieties are the 4-fluorophenyl group, which is necessarily flat (r.m.s deviation = 0.0106 Å), and the bis(methylsulfanyl)propenone group (atoms C7, O1, C8, C9, S1, S2, C10, C11), which is also close to planarity [r.m.s. = 0.0315 Å, maximum deviation = 0.0412 (1) Å at C9]. The dihedral angle between these two planar regions is 32.23 (4)°. Representative torsion angles are given in Table 1.

Table 1
Conformation-defining torsion angles (°) in I

Atoms	Torsion angle	Dihedral angle
C5—C4—C7—O1	−28.68 (16)
C4—C7—C8—C9	−172.66 (10)
O1—C7—C8—C9	4.91 (18)
C7—C8—C9—S1	175.43 (9)
C7—C8—C9—S2	−2.57 (16)
C8—C9—S1—C10	0.01 (13)
C8—C9—S2—C11	177.09 (10)

Planar groups
4-F—Ph/b-MSP		32.23 (4)
4-F—Ph is 4-fluorophenyl, atoms C1–C6, F1 and b-MSP is bis(methylsulfanyl)propenone, atoms C7–C11, O1, S1, S2.

Figure 1
An ellipsoid plot (50% probability) of I. Hydrogen atoms are drawn as small arbitrary circles.

3. Supramolecular features

There are no conventional hydrogen bonds in the crystal structure of I, nor any π–π stacking of aromatic rings. There are, however, several weaker C—H⋯O and C—H⋯S close contacts, which are summarized in Table 2. Contacts C2—H2⋯O1ⁱ and C10—H10C⋯O1ⁱⁱ [d_D⋯A = 3.4530 (15) and 3.4724 (16) Å] join the molecules into layers parallel to the ab plane, as shown in Fig. 2. The C11—H11A⋯S1ⁱⁱⁱ and C11—H11C⋯S2^iv contacts [d_D⋯A = 3.6032 (14) and 3.6292 (13) Å; all symmetry codes as per Table 2] join molecules into tapes that extend along the b-axis direction, roughly parallel to [307]. The 4-fluorophenyl groups of adjacent tapes interdigitate. These interactions are shown in Fig. 3. A Hirshfeld surface analysis conducted using Crystal Explorer 21 (Spackman et al., 2021 ) shows that over 90% of intermolecular contacts involve hydrogen. The 2D fingerprint plots of the five most abundant atom–atom contacts are shown in Fig. 4.

Table 2
Close contacts (Å, °) in crystalline I

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.95	2.53	3.4530 (15)	163
C10—H10C⋯O1ⁱⁱ	0.98	2.50	3.4724 (16)	175
C11—H11A⋯S1ⁱⁱⁱ	0.98	3.01	3.6032 (14)	120
C11—H11C⋯S2^iv	0.98	3.01	3.6292 (13)	122
Symmetry codes: (i) x − 1, y, z; (ii) x, y − 1, z; (iii) −x + 2, −y, −z; (iv) −x + 2, −y + 1, −z.

Figure 2
A partial packing plot of I viewed normal to the ab plane. C—H⋯O interactions that connect the molecules into layers are shown as open dashed lines.

Figure 3
A partial packing plot of I viewed approximately perpendicular to [307], showing tapes of molecules interacting via C—H⋯S and C—H⋯O contacts. The 4-fluorophenyl groups of adjacent tapes interdigitate.

Figure 4
Hirshfeld-surface two-dimensional fingerprint plots showing (a) all contacts, (b) H⋯H contacts, (c) C⋯H contacts, (d) F⋯H contacts, (e) S⋯H contacts, and (f) O⋯H contacts.

4. Database survey

A search of the Cambridge Structural Database (CSD, v5.46, November 2024; Groom et al., 2016 ) using a fragment consisting of I but with the fluorine position set to ‘any atom', returned 29 hits, three of which were duplicates. However, only six of these had a hydrogen attached to the central carbon of the propene moiety (i.e., C8 in I). Of these six, KUQQEV (Madan Kumar et al., 2020 ) had chlorine at the ortho position of the benzene ring, while WENVIV (Liao et al., 2006 ) had a 2,6-dimethyl-3,5-dinitro-4-^tBu phenyl group. The remaining four structures with para-substituted phenyl groups are thus the most similar to I. Entry MTBZOE (Mellor & Nyburg, 1971 ) has X = H, OCUSEN (Verma & Singh, 2016 ) has X = OMe, LUYXAH (Hussain et al., 2018 ) has X = CF₃, and AFOMEP (Yu et al., 2013 ) has X = NO₂.

5. Synthesis and crystallization

Synthesis of I was as described in the literature procedure by Huynh et al. (2025 ). The product obtained was purified by column chromatography and recrystallized from chloroform by slow evaporation, yielding reddish brown crystals (m.p.: 358–359 K).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All hydrogen atoms were found in difference-Fourier maps, but subsequently included in the refinement using riding models, with constrained distances set to 0.95 Å (Csp²—H) and 0.98 Å (RCH₃). U_iso(H) parameters were set to values of either 1.2U_eq or 1.5U_eq (RCH₃) of the attached atom.

Table 3
Experimental details

Crystal data
Chemical formula	C₁₁H₁₁FOS₂
M_r	242.32
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	7.6956 (3), 8.6895 (4), 8.9468 (4)
α, β, γ (°)	74.633 (2), 83.237 (2), 73.008 (2)
V (Å³)	551.18 (4)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.47
Crystal size (mm)	0.24 × 0.22 × 0.16

Data collection
Diffractometer	Bruker D8 Venture dual source
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.919, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	15392, 2490, 2343
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.065, 1.11
No. of reflections	2490
No. of parameters	138
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.20
Computer programs: APEX5 (Bruker, 2023 ), SHELXT (Sheldrick, 2015a ), SHELXL2019/3 (Sheldrick, 2015b ), XP in SHELXTL (Sheldrick, 2008 ), SHELX (Sheldrick, 2008) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2449698

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989025004189/nx2025sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025004189/nx2025Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025004189/nx2025Isup3.cml

checkCIF report

Computing details top

1-(4-Fluorophenyl)-3,3-bis(methylsulfanyl)prop-2-en-1-one top

Crystal data top

C₁₁H₁₁FOS₂	Z = 2
M_r = 242.32	F(000) = 252
Triclinic, P1	D_x = 1.460 Mg m⁻³
a = 7.6956 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6895 (4) Å	Cell parameters from 9984 reflections
c = 8.9468 (4) Å	θ = 2.5–27.5°
α = 74.633 (2)°	µ = 0.47 mm⁻¹
β = 83.237 (2)°	T = 100 K
γ = 73.008 (2)°	Irregular block, pale yellow
V = 551.18 (4) Å³	0.24 × 0.22 × 0.16 mm

Data collection top

Bruker D8 Venture dual source diffractometer	2490 independent reflections
Radiation source: microsource	2343 reflections with I > 2σ(I)
Detector resolution: 7.41 pixels mm^-1	R_int = 0.030
φ and ω scans	θ_max = 27.6°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −9→9
T_min = 0.919, T_max = 0.971	k = −11→11
15392 measured reflections	l = −11→11

Refinement top

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)] = 0.025	Hydrogen site location: difference Fourier map
wR(F²) = 0.065	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0239P)² + 0.2301P] where P = (F_o² + 2F_c²)/3
2490 reflections	(Δ/σ)_max = 0.001
138 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

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).

Diffraction data were collected with the crystal at 100K.

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
S1	0.73029 (4)	0.09565 (3)	0.14124 (4)	0.02169 (9)
S2	0.86839 (4)	0.38315 (3)	0.11708 (3)	0.01940 (9)
F1	−0.1801 (1)	0.82639 (9)	0.51997 (9)	0.02883 (18)
O1	0.60092 (12)	0.62516 (11)	0.20784 (11)	0.02322 (19)
C1	−0.01976 (16)	0.75951 (14)	0.44890 (14)	0.0204 (2)
C2	−0.01958 (16)	0.65680 (14)	0.35558 (14)	0.0204 (2)
H2	−0.128882	0.636203	0.337248	0.024*
C3	0.14619 (16)	0.58411 (14)	0.28895 (13)	0.0179 (2)
H3	0.151092	0.509778	0.226525	0.022*
C4	0.30527 (15)	0.61861 (13)	0.31233 (13)	0.0164 (2)
C5	0.29726 (16)	0.72591 (14)	0.40625 (13)	0.0189 (2)
H5	0.404818	0.751305	0.421626	0.023*
C6	0.13410 (17)	0.79576 (14)	0.47728 (13)	0.0209 (2)
H6	0.128543	0.866486	0.543524	0.025*
C7	0.48552 (15)	0.54676 (14)	0.23854 (13)	0.0170 (2)
C8	0.51887 (15)	0.38341 (14)	0.21175 (13)	0.0175 (2)
H8	0.421370	0.333400	0.230166	0.021*
C9	0.68359 (15)	0.29796 (14)	0.16136 (13)	0.0162 (2)
C10	0.52183 (19)	0.04166 (18)	0.1997 (2)	0.0401 (4)
H10A	0.427160	0.114877	0.128935	0.060*
H10B	0.485417	0.054133	0.305480	0.060*
H10C	0.538334	−0.073697	0.196746	0.060*
C11	1.05048 (17)	0.21702 (16)	0.06748 (17)	0.0281 (3)
H11A	1.011950	0.178453	−0.013365	0.042*
H11B	1.080620	0.125082	0.159713	0.042*
H11C	1.157774	0.257288	0.029136	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01867 (15)	0.01518 (15)	0.03124 (17)	−0.00221 (11)	0.00121 (11)	−0.00935 (11)
S2	0.01558 (14)	0.01870 (15)	0.02352 (16)	−0.00553 (11)	0.00205 (10)	−0.00475 (11)
F1	0.0243 (4)	0.0261 (4)	0.0333 (4)	−0.0021 (3)	0.0106 (3)	−0.0129 (3)
O1	0.0202 (4)	0.0196 (4)	0.0332 (5)	−0.0087 (3)	0.0035 (3)	−0.0104 (4)
C1	0.0199 (5)	0.0162 (5)	0.0199 (5)	−0.0001 (4)	0.0050 (4)	−0.0036 (4)
C2	0.0182 (5)	0.0189 (5)	0.0235 (6)	−0.0045 (4)	−0.0002 (4)	−0.0051 (5)
C3	0.0200 (5)	0.0165 (5)	0.0182 (5)	−0.0048 (4)	0.0001 (4)	−0.0064 (4)
C4	0.0188 (5)	0.0133 (5)	0.0164 (5)	−0.0037 (4)	−0.0001 (4)	−0.0033 (4)
C5	0.0217 (6)	0.0154 (5)	0.0206 (5)	−0.0053 (4)	−0.0018 (4)	−0.0054 (4)
C6	0.0288 (6)	0.0156 (5)	0.0181 (5)	−0.0036 (5)	−0.0005 (5)	−0.0067 (4)
C7	0.0175 (5)	0.0158 (5)	0.0180 (5)	−0.0039 (4)	−0.0013 (4)	−0.0051 (4)
C8	0.0168 (5)	0.0158 (5)	0.0213 (5)	−0.0058 (4)	0.0007 (4)	−0.0062 (4)
C9	0.0170 (5)	0.0153 (5)	0.0165 (5)	−0.0043 (4)	−0.0016 (4)	−0.0039 (4)
C10	0.0246 (7)	0.0231 (7)	0.0798 (12)	−0.0105 (5)	0.0089 (7)	−0.0250 (7)
C11	0.0165 (6)	0.0223 (6)	0.0380 (7)	−0.0008 (5)	0.0055 (5)	−0.0024 (5)

Geometric parameters (Å, º) top

S1—C9	1.7421 (11)	C4—C7	1.4988 (15)
S1—C10	1.7831 (14)	C5—C6	1.3856 (16)
S2—C9	1.7478 (11)	C5—H5	0.9500
S2—C11	1.8043 (13)	C6—H6	0.9500
F1—C1	1.3626 (13)	C7—C8	1.4461 (15)
O1—C7	1.2349 (14)	C8—C9	1.3617 (16)
C1—C2	1.3740 (17)	C8—H8	0.9500
C1—C6	1.3772 (18)	C10—H10A	0.9800
C2—C3	1.3896 (16)	C10—H10B	0.9800
C2—H2	0.9500	C10—H10C	0.9800
C3—C4	1.3930 (16)	C11—H11A	0.9800
C3—H3	0.9500	C11—H11B	0.9800
C4—C5	1.3959 (15)	C11—H11C	0.9800

C9—S1—C10	104.24 (6)	O1—C7—C4	119.6 (1)
C9—S2—C11	103.35 (6)	C8—C7—C4	117.69 (10)
F1—C1—C2	118.27 (11)	C9—C8—C7	123.03 (10)
F1—C1—C6	118.14 (11)	C9—C8—H8	118.5
C2—C1—C6	123.57 (11)	C7—C8—H8	118.5
C1—C2—C3	117.63 (11)	C8—C9—S1	123.59 (9)
C1—C2—H2	121.2	C8—C9—S2	121.74 (9)
C3—C2—H2	121.2	S1—C9—S2	114.64 (6)
C2—C3—C4	120.99 (11)	S1—C10—H10A	109.5
C2—C3—H3	119.5	S1—C10—H10B	109.5
C4—C3—H3	119.5	H10A—C10—H10B	109.5
C3—C4—C5	119.11 (10)	S1—C10—H10C	109.5
C3—C4—C7	122.54 (10)	H10A—C10—H10C	109.5
C5—C4—C7	118.34 (10)	H10B—C10—H10C	109.5
C6—C5—C4	120.71 (11)	S2—C11—H11A	109.5
C6—C5—H5	119.6	S2—C11—H11B	109.5
C4—C5—H5	119.6	H11A—C11—H11B	109.5
C1—C6—C5	117.96 (11)	S2—C11—H11C	109.5
C1—C6—H6	121.0	H11A—C11—H11C	109.5
C5—C6—H6	121.0	H11B—C11—H11C	109.5
O1—C7—C8	122.67 (10)

F1—C1—C2—C3	−177.42 (10)	C5—C4—C7—O1	−28.68 (16)
C6—C1—C2—C3	1.11 (18)	C3—C4—C7—C8	−31.93 (16)
C1—C2—C3—C4	−1.97 (17)	C5—C4—C7—C8	148.97 (11)
C2—C3—C4—C5	1.02 (17)	O1—C7—C8—C9	4.91 (18)
C2—C3—C4—C7	−178.08 (10)	C4—C7—C8—C9	−172.66 (10)
C3—C4—C5—C6	0.87 (17)	C7—C8—C9—S1	175.43 (9)
C7—C4—C5—C6	−179.99 (10)	C7—C8—C9—S2	−2.57 (16)
F1—C1—C6—C5	179.24 (10)	C10—S1—C9—C8	0.01 (13)
C2—C1—C6—C5	0.71 (18)	C10—S1—C9—S2	178.14 (8)
C4—C5—C6—C1	−1.71 (17)	C11—S2—C9—C8	177.09 (10)
C3—C4—C7—O1	150.42 (11)	C11—S2—C9—S1	−1.08 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.95	2.53	3.4530 (15)	163
C10—H10C···O1ⁱⁱ	0.98	2.50	3.4724 (16)	175
C11—H11A···S1ⁱⁱⁱ	0.98	3.01	3.6032 (14)	120
C11—H11C···S2^iv	0.98	3.01	3.6292 (13)	123

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

Conformation-defining torsion angles (°) in I top

Atoms	Torsion angle	Dihedral angle
C5—C4—C7—O1	-28.68 (16)
C4—C7—C8—C9	-172.66 (10)
O1—C7—C8—C9	4.91 (18)
C7—C8—C9—S1	175.43 (9)
C7—C8—C9—S2	-2.57 (16)
C8—C9—S1—C10	0.01 (13)
C8—C9—S2—C11	177.09 (10)

Planar groups
4-F-Ph/b-MSP		32.23 (4)

4-F-Ph is 4-fluorophenyl, atoms C1–C6, F1 and b-MSP is bis(methylsulfanyl)propenone, atoms C7–C11, O1, S1, S2.

Close contacts (Å, °) in crystalline I top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.95	2.53	3.4530 (15)	163.1
C10—H10C···O1ⁱⁱ	0.98	2.50	3.4724 (16)	174.8
C11—H11A···S1ⁱⁱⁱ	0.98	3.01	3.6032 (14)	120.1
C11—H11C···S2^iv	0.98	3.01	3.6292 (13)	122.5

Symmetry codes: (i) x - 1, y, z; (ii) x, y - 1, z; (iii) -x + 2, -y, -z; (iv) -x + 2, -y + 1, -z.

Acknowledgements

One of the authors (HSY) thanks the UGC, New Delhi, for the award of UGC BSR Faculty Fellowship for a period of three years. The D8 Venture diffractometer was funded by the NSF (MRI CHE1625732), and by the University of Kentucky.

References

Aneja, B., Arif, R., Perwez, A., Napoleon, J. V., Hassan, P., Rizvi, M. M. A., Azam, A., Rahisuddin & Abid, M. (2018). ChemistrySelect 2018, 3, 2638–2645. Google Scholar
Belahlou, H., Waszkowska, K., Bouraiou, A., Bendeif, E., Taboukhat, S., Bouchouit, K. & Sahraoui, B. (2020). Opt. Mater. 108, 110188. CSD CrossRef Google Scholar
Bhat, B. A., Dhar, K. L., Puri, S. C., Saxena, A. K., Shanmugavel, M. & Qazi, G. N. (2005). Bioorg. Med. Chem. Lett. 15, 3177–3180. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2023). APEX5. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Corredor, C. C., Huang, Z. L., Belfield, K. D., Morales, A. R. & Bondar, M. V. (2007). Chem. Mater. 19, 5165–5173. CrossRef CAS Google Scholar
de Mello, M. V. P., Abrahim-Vieira, B. A., Domingos, T. F. S., Jesus, J. B., de Sousa, A. C. C., Rodrigues, C. R. & de Souza, A. M. T. (2018). Eur. J. Med. Chem. 150, 920–929. CrossRef PubMed Google Scholar
Elkanzi, N. A. A., Hrichi, H., Alolayan, R. A., Derafa, W., Zahou, F. M. & Bakr, R. B. (2022). ACS Omega, 7, 27769–27786. Web of Science CrossRef CAS PubMed Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Hussain, M. V., Kumar, S., Vinayaka, A. C., Babu, T. B., Devika, B. G., Rajesh, B. M. & Doreswamy, B. H. (2018). J. Applicable Chem. 7, 19–28. CAS Google Scholar
Huynh, T. N. T., Nguyen, K. T., Krongyut, C., Lai, R.-Y., Sukwattanasinitt, M. & Wacharasindhu, S. (2025). Org. Biomol. Chem. 23, 1923–1929. CrossRef CAS PubMed Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
Lahtchev, K. L., Batovska, D. I., Parushev, P., Ubiyvovk, V. M. & Sibirny, A. A. (2008). Eur. J. Med. Chem. 43, 2220–2228. Web of Science CrossRef PubMed CAS Google Scholar
Liao, J.-P., Zhang, T., Yu, C.-Y. & Huang, Z.-T. (2006). Acta Cryst. E62, o4537–o4538. CSD CrossRef IUCr Journals Google Scholar
Lin, Y. M., Zhou, Y., Flavin, M. T., Zhou, L. M., Nie, W. & Chen, F. C. (2002). Bioorg. Med. Chem. 10, 2795–2802. Web of Science CrossRef PubMed CAS Google Scholar
Madan Kumar, S., Hemraju, B., Anil, S., Manjunatha, N., Swamy, M., Lokanath, N., Al-Ghorbani, M., Al-Zaqri, N. & Alsalme, A. (2020). Z. Kristallogr. Cryst. Mater. 235, 85–93. CrossRef CAS Google Scholar
Mellor, I. P. & Nyburg, S. C. (1971). Acta Cryst. B27, 1954–1958. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Nakamura, C., Kawasaki, N., Miyataka, H., Jayachandran, E., Kim, I., Kirk, K. L., Taguchi, T., Takeuchi, Y., Hori, H. & Satoh, T. (2002). Bioorg. Med. Chem. 10, 699–706. Web of Science CrossRef PubMed CAS Google Scholar
Nowakowska, Z. (2007). Eur. J. Med. Chem. 42, 125–137. Web of Science CrossRef PubMed CAS Google Scholar
Opletalova, V. & Sedivy, D. (1999). Ceska Slov. Farm. 48, 252–255. PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D. & Spackman, M. A. (2021). J. Appl. Cryst. 54, 1006–1011. Web of Science CrossRef CAS IUCr Journals Google Scholar
Trivedi, J. C., Bariwal, J. B., Upadhyay, K. D., Naliapara, Y. T., Joshi, S. K., Pannecouque, C. C., De Clercq, E. & Shah, A. K. (2007). Tetrahedron Lett. 48, 8472–8474. Web of Science CrossRef CAS Google Scholar
Verma, G. K. & Singh, M. S. (2016). CSD Communication (Refcode OCUSEN). CCDC, Cambridge, England. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, Y., Noirbent, G., Brunel, D., Ding, Z., Gigmes, D., Graff, B., Xiao, P., Dumur, F. & Lalevée, J. (2020). Polym. Chem. 11, 5767–5777. CrossRef CAS Google Scholar
Yu, G.-N., Xia, J.-H., Xu, Z.-H., Wang, L.-B. & Yu, C.-Y. (2013). Acta Cryst. E69, o1036. CSD CrossRef IUCr Journals Google Scholar
Zhuang, C., Zhang, W., Sheng, C., Zhang, W., Xing, C. & Miao, Z. (2017). Chem. Rev. 117, 7762–7810. Web of Science CrossRef CAS PubMed Google Scholar

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