Crystal structure and Hirshfeld surface analysis of 4-bromo-2-chloro­phenyl (E)-3-[4-(undec­yloxy)phen­yl]acrylate

Devarajegowda, H.C.; Palakshamurthy, B.S.; Anil Kumar, H.; Srinivasa, H.T.; Harish Kumar, M.

doi:10.1107/S2056989025007078

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ISSN: 2056-9890

Volume 81| Part 9| September 2025| Pages 836-839

https://doi.org/10.1107/S2056989025007078

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Crystal structure and Hirshfeld surface analysis of 4-bromo-2-chlorophenyl (E)-3-[4-(undecyloxy)phenyl]acrylate

H. C. Devarajegowda,^a B. S. Palakshamurthy,^b H. Anil Kumar,^c H. T. Srinivasa ^d and M. Harish Kumar ^a ^*

^aDepartment of Physics, Yuvaraja's College, University of Mysore, Mysore 570005, Karnataka, India, ^bDepartment of PG Studies and Research in Physics, Albert Einstein Block, UCS, Tumkur University, Tumkur, Karnataka-572103, India, ^cDepartment of Physics, Government First Grade College, Chikkabalapura, Karnataka-562101, India, and ^dRaman Research Institute, C. V. Raman Avenue, Sadashivanagar, Bangalore, Karnataka-560080, India
^*Correspondence e-mail: [email protected]

Edited by F. F. Ferreira, Universidade Federal do ABC, Brazil (Received 18 June 2025; accepted 5 August 2025; online 15 August 2025)

In the title compound, C₂₆H₃₂BrClO₃, the dihedral angle between the 4-bromo-2-chlorophenyl ring and the aromatic ring of (alkyloxy)phenyl moiety is found to be 77.21 (2)°. The torsion angle associated with the ester moiety is 173.2 (2)° which is anti-periplanar. In the crystal, intermolecular C—H⋯O hydrogen bonding links the molecules into cyclic hydrogen-bonded inversion dimers with R²₂(10) motifs. The molecular structure is associated with an inversion centre and connected through two symmetrical C—H⋯O interactions, forming R²₂(10) inversion dimer motif. The packing is further consolidated by C—H⋯π and C—Cl⋯π interactions. Hirshfeld surface analysis showed that the most significant contributions are from H⋯H (54.0%), C⋯H/H⋯C (15.2%), Br⋯H/H⋯Br (10.9%), O⋯H/H⋯O (7.8%) and Cl⋯H/H⋯Cl (2.6%) contacts.

Keywords: crystal structure; 4-bromo-2-chlorophenyl; Hirshfeld surface.

CCDC reference: 2478544

1. Chemical context

Compounds based on the 4-bromo-2-chlorophenyl scaffold are found to exhibit potent in vitro inhibitory activity against Plasmodium falciparum, making them promising candidates as transmission-blocking agents for malaria treatment (Vallone et al., 2018 ; Kos et al., 2022 ). The incorporation of halogen substituents in the phenyl ring is known to enhance antimicrobial activity in such molecules (Radwan et al., 2014 ). Acrylate derivatives have demonstrated antitumor potential by inhibiting tubulin polymerization at the cellular level (Pieters et al., 1999 ; Jung et al., 2019 ). The presence and prolongation of alkyl groups in the various drug molecules are found to enhance the penetration of the compounds into cells, which make the molecules efficient as drugs. In this context, it is found that caffeic acid phosphanium salt combined with alkyl chains acquire anticancer properties (Lukáč et al., 2024 ), whereas cinnamic acid-based molecules coupled with alkyl groups exhibit anti-tuberculosis activity (De et al., 2011 ). Furthermore, increasing the alkyl chain length on amido functional groups has been shown to improve the anti-inflammatory activities of certain drugs (Matta et al., 2020 ). Studies on 4-bromophenyl piperidine derivatives revealed strong binding affinities towards the COVID-19 main protease, indicating potential antiviral activities (Lorin et al., 2024 ). Similarly, chlorophenyl derivatives have demonstrated inhibitory effects against the SARS-CoV-2 main protease. Despite the promising pharmacological potential, limited research has been conducted on the medicinal significance of 4-bromo-2-chlorophenyl scaffolds. In view of this gap, we aimed to design and synthesize a novel series of compounds incorporating this moiety. Herein, we present the synthesis and characterization of the title compound, constructed by coupling the 4-bromo-2-chlorophenyl unit with a (undecyloxy)phenyl fragment through an ester linkage.

2. Structural commentary

The title compound (Fig. 1) crystallizes in the space group P $[\overline{1}]$ . The molecule is nearly planar with an r.m.s deviation of 0.076 Å. The dihedral angle between the mean planes of the 4-bromo-2-chlorophenyl ring and the aromatic ring of the (alkyloxy)phenyl moiety is 77.21 (2)°. With respect to the alkyl chain (O3–C26), the dihedral angle formed with the 4-bromo-2-chlorophenyl ring is 66.94 (2)°, while that with the phenyl ring is 10.59 (2)°, indicating a more coplanar orientation between the alkyl chain and the phenyl ring. The torsion angle associated with the ester moiety (C1—O1—C7—C8) is 173.1 (2)°, which is anti-periplanar. The molecule does not show any significant deviations in bond distances or angles.

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

3. Supramolecular features

In the crystal, C—H⋯O hydrogen bonding links the molecules into cyclic hydrogen-bonded inversion dimers with R₂²(10) motifs (Table 1, Fig. 2). The crystal packing is further consolidated by weak C—H⋯π interactions (Table 1, Fig. 3). In addition, a weak non-covalent C—Cl⋯π halogen⋯π interaction arising from the electrostatic attraction between the electron-deficient chlorine atom and the electron-rich π-system connects the molecules along the a-axis direction [Cl⋯Cg1 distance = 3.6415 (15) Å; Cg1 is the centroid for the 4-bromo-2-chlorophenyl ring (C1–C6); Fig. 4].

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O2ⁱ	0.93	2.35	3.248 (3)	164
C16—H16A⋯Cg2ⁱⁱ	0.97	2.95	3.824 (3)	150
Symmetry codes: (i) ; (ii) .

Figure 2
The molecular packing with intermolecular C—H⋯O interactions depicted by dashed pale- green coloured lines. Symmetry code: (i) −x − 1, −y + 1, −z + 1.

Figure 3
The crystal packing with the C—H⋯π interactions depicted by dashed pale-green lines. Cg2 is the centroid of the (C10–C15)(x + 1, y, z) ring.

Figure 4
The crystal packing with weak C—Cl⋯Cg1 interactions depicted by dashed pale-green lines. Cg1 is the centroid of the C1–C6 ring.

4. Hirshfeld surface analysis

The Hirshfeld surface (Spackman & Jayatilaka, 2009 ) and two-dimensional fingerprint plots (McKinnon et al., 2007 ) were generated using CrystalExplorer17 (Spackman et al., 2021 ) to investigate the intermolecular interactions. The Hirshfeld surface mapped over d_norm is shown in Fig. 5. The prominent red spots on the iso-surface indicate the presence of significant intermolecular hydrogen-bond interactions, specifically C9—H9⋯O2, which play a stabilizing role in the crystal packing. The corresponding 2D fingerprint plots are shown in Fig. 6, quantifying the contribution of various intermolecular interactions to the overall crystal packing. The most significant contributions arise from H⋯H (54.0%), followed by C⋯H/H⋯C (15.3%), Br⋯H/H⋯Br (10.9%), O⋯H/H⋯O (7.7%) and Cl⋯H/H⋯Cl (4.5%) contacts. The sharp spikes in the 2D fingerprint plots correspond to the C9—H9⋯O2 hydrogen bond (O⋯H/H⋯O).

Figure 5
The Hirshfeld surface of the title compound plotted over d_norm with dashed lines indicating hydrogen bonds.

Figure 6
The two-dimensional fingerprint plots for the title compound, showing all interactions, and delineated into H⋯H, C⋯H/H⋯C, Br⋯H/H⋯Br, O⋯H/H⋯O, Cl⋯C/C⋯Cl, Cl⋯H/H⋯Cl, Cl⋯O/O⋯Cl, O⋯C/C⋯O, Cl⋯Cl, C⋯C, O⋯O and Br⋯C/C⋯Br interactions.

5. Database Survey

A search of the Cambridge Structural Database (CSD version 2.0.4, December 2024; Groom et al., 2016 ) for molecules containing the 4-bromo-2-chlorophenyl moiety resulted in 15 matches. Among these, the five compounds with CSD codes EBEPUZ (Lehmler et al., 2013 ), ISOJUX (Koti Reddy et al., 2016 ), FANFOS (Sangeeta et al., 2017 ), VIDQUX (Mohan et al., 2018 ) and EJULUT (Dumitrescu et al., 2020 ), are found to be substituted with fragments containing alkyloxy chains or substituted aromatic or heterocyclic rings that are in same plane. The dihedral angles between these planes and the 4-bromo-2-chlorophenyl moiety are 59.0, 75.3, 88.78, 37.47, and 2.99°. In the title compound, the dihedral angle between the 4-bromo-2-chlorophenyl ring and the planar (undecyloxy)phenyl)acrylate fragment is found to be 74.23 (3)°. The torsion angle between the ortho-substituted chlorine atom and the first atom of the planar side chain in the above compounds is between 1 to 4° whereas in the title compound it is 5.30 (4)°.

6. Synthesis and crystallization

A mixture of 4-bromo-2-chlorophenol (0.208 g, 0.001 mol) and (E)-3-[4-(undecyloxy)phenyl]acrylic acid (0.319 g, 0.001 mol) was suspended in anhydrous chloroform (10 ml). To this, N,N-dicyclohexylcarbodiimide (0.206 g, 0.001 mol) and 4-N,N-dimethylamino pyridine (5 mg) was added and the mixture stirred overnight at room temperature.

The N,N-dicyclohexyl urea formed was filtered off and the filtrate diluted with chloroform (25 ml). This solution was washed successively with 5% aqueous acetic acid solution (2 × 25 ml) and water (2 × 25 ml) and dried on sodium sulfate. The residue obtained on removal of solvent was chromatographed on silica gel using chloroform as eluent. Removal of solvent from the eluate afforded a white material, which was crystallized from a chloroform–petroleum ether mixture. Yield (0.385 g, 73%), m.p. 338–340 K. Elemental analysis, calculated: C, 61.49; H, 6.35; Br, 15.73; Cl, 6.98; O, 9.45%, found: C, 61.52; H, 6.38; Br, 15.76; Cl, 6.95%.

7. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined using a riding model with U_iso(H) = k*U_eq(C), where k= 1.5 for methyl hydrogen atoms and 1.2 for all others.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₆H₃₂BrClO₃
M_r	507.87
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	5.5111 (8), 9.5856 (15), 23.532 (4)
α, β, γ (°)	81.251 (4), 86.986 (4), 88.012 (4)
V (Å³)	1226.5 (3)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.81
Crystal size (mm)	0.27 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.6, 0.7
No. of measured, independent and observed [I > 2σ(I)] reflections	17380, 6085, 5080
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.114, 1.09
No. of reflections	6085
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.90, −0.96
Computer programs: APEX2 and SAINT (Bruker, 2014 ), SHELXT (Sheldrick, 2015a ), SHELXL2019/2 (Sheldrick, 2015b ), Mercury (Macrae et al., 2020 ) and publCIF (Westrip,2010 ).

Supporting information

CCDC reference: 2478544

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989025007078/ee2016sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S2056989025007078/ee2016Isup3.cml

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025007078/ee2016Isup3.hkl

checkCIF report

Computing details top

4-Bromo-2-chlorophenyl (E)-3-[4-(undecyloxy)phenyl]prop-2-enoate top

Crystal data top

C₂₆H₃₂BrClO₃	Z = 2
M_r = 507.87	F(000) = 528
Triclinic, P1	D_x = 1.375 Mg m⁻³
a = 5.5111 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5856 (15) Å	Cell parameters from 5080 reflections
c = 23.532 (4) Å	θ = 2–28.4°
α = 81.251 (4)°	µ = 1.81 mm⁻¹
β = 86.986 (4)°	T = 296 K
γ = 88.012 (4)°	Prism, colourless
V = 1226.5 (3) Å³	0.27 × 0.24 × 0.20 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	6085 independent reflections
Radiation source: fine-focus sealed tube	5080 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
Detector resolution: 1.02 pixels mm^-1	θ_max = 28.4°, θ_min = 2.6°
φ and Ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −12→12
T_min = 0.6, T_max = 0.7	l = −31→31
17380 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0321P)² + 1.7821P] where P = (F_o² + 2F_c²)/3
6085 reflections	(Δ/σ)_max = 0.001
281 parameters	Δρ_max = 0.90 e Å⁻³
0 restraints	Δρ_min = −0.96 e Å⁻³
0 constraints

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
Br1	−1.44231 (6)	0.07449 (4)	0.72273 (2)	0.03026 (10)
Cl1	−0.69598 (12)	−0.02663 (8)	0.56674 (3)	0.02653 (16)
O2	−0.7521 (3)	0.3939 (2)	0.51095 (8)	0.0204 (4)
O3	0.2021 (3)	0.4438 (2)	0.21602 (8)	0.0203 (4)
O1	−0.9273 (4)	0.2016 (2)	0.48915 (8)	0.0224 (4)
C4	−1.2718 (5)	0.1195 (3)	0.65019 (11)	0.0181 (5)
C10	−0.2950 (4)	0.4111 (3)	0.35655 (10)	0.0146 (5)
C12	0.0467 (5)	0.5320 (3)	0.30290 (11)	0.0175 (5)
H12	0.158485	0.603779	0.298670	0.021*
C13	0.0446 (4)	0.4401 (3)	0.26272 (10)	0.0157 (5)
C7	−0.7748 (4)	0.3133 (3)	0.47730 (11)	0.0148 (5)
C3	−1.0695 (5)	0.0384 (3)	0.63777 (11)	0.0196 (5)
H3	−1.013572	−0.035248	0.664720	0.024*
C5	−1.3567 (5)	0.2311 (3)	0.61188 (11)	0.0186 (5)
H5	−1.490918	0.285355	0.621850	0.022*
C1	−1.0382 (5)	0.1795 (3)	0.54418 (11)	0.0169 (5)
C8	−0.6485 (4)	0.3140 (3)	0.42096 (11)	0.0159 (5)
H8	−0.697304	0.256542	0.395425	0.019*
C11	−0.1211 (4)	0.5154 (3)	0.34965 (11)	0.0160 (5)
H11	−0.117004	0.575513	0.377070	0.019*
C2	−0.9519 (5)	0.0700 (3)	0.58382 (11)	0.0177 (5)
C17	0.5323 (5)	0.5294 (3)	0.15377 (11)	0.0180 (5)
H17A	0.429058	0.523176	0.122165	0.022*
H17B	0.620095	0.439804	0.162346	0.022*
C6	−1.2378 (5)	0.2615 (3)	0.55788 (11)	0.0189 (5)
H6	−1.292326	0.336328	0.531272	0.023*
C15	−0.2948 (5)	0.3201 (3)	0.31520 (11)	0.0174 (5)
H15	−0.409570	0.250043	0.318702	0.021*
C16	0.3751 (5)	0.5544 (3)	0.20594 (11)	0.0184 (5)
H16A	0.473556	0.551762	0.239077	0.022*
H16B	0.292172	0.645838	0.198952	0.022*
C18	0.7136 (5)	0.6456 (3)	0.13518 (11)	0.0186 (5)
H18A	0.813274	0.654416	0.167141	0.022*
H18B	0.626185	0.734666	0.124933	0.022*
C9	−0.4608 (4)	0.3998 (3)	0.40721 (10)	0.0153 (5)
H9	−0.432562	0.460077	0.433465	0.018*
C19	0.8772 (5)	0.6149 (3)	0.08386 (11)	0.0182 (5)
H19A	0.971302	0.528723	0.095216	0.022*
H19B	0.775702	0.598798	0.053172	0.022*
C23	1.5469 (5)	0.7803 (3)	−0.06600 (11)	0.0187 (5)
H23A	1.640127	0.694139	−0.054020	0.022*
H23B	1.443821	0.762871	−0.096192	0.022*
C20	1.0514 (5)	0.7326 (3)	0.06060 (11)	0.0185 (5)
H20A	1.154647	0.748415	0.091027	0.022*
H20B	0.958141	0.819163	0.049260	0.022*
C14	−0.1262 (5)	0.3332 (3)	0.26937 (11)	0.0183 (5)
H14	−0.125992	0.270754	0.242746	0.022*
C21	1.2113 (5)	0.6993 (3)	0.00905 (11)	0.0184 (5)
H21A	1.304137	0.612633	0.020503	0.022*
H21B	1.107613	0.683149	−0.021230	0.022*
C25	1.8825 (5)	0.8593 (3)	−0.14085 (12)	0.0217 (6)
H25A	1.780445	0.842081	−0.171282	0.026*
H25B	1.974251	0.772814	−0.128449	0.026*
C24	1.7217 (5)	0.8967 (3)	−0.09043 (11)	0.0189 (5)
H24A	1.628795	0.982639	−0.102987	0.023*
H24B	1.823950	0.915000	−0.060221	0.023*
C22	1.3861 (5)	0.8153 (3)	−0.01485 (11)	0.0189 (5)
H22A	1.488999	0.832089	0.015483	0.023*
H22B	1.293413	0.901732	−0.026726	0.023*
C26	2.0588 (6)	0.9755 (3)	−0.16466 (13)	0.0295 (7)
H26A	2.157249	0.946694	−0.195930	0.044*
H26B	2.161360	0.992456	−0.134811	0.044*
H26C	1.968879	1.060577	−0.178209	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03308 (17)	0.03720 (19)	0.01798 (14)	−0.00773 (13)	0.01127 (11)	0.00119 (11)
Cl1	0.0175 (3)	0.0268 (4)	0.0378 (4)	0.0014 (3)	0.0032 (3)	−0.0148 (3)
O2	0.0206 (9)	0.0218 (10)	0.0197 (9)	−0.0075 (8)	0.0081 (7)	−0.0078 (8)
O3	0.0223 (9)	0.0216 (10)	0.0170 (9)	−0.0089 (8)	0.0112 (7)	−0.0049 (7)
O1	0.0266 (10)	0.0254 (10)	0.0166 (9)	−0.0153 (8)	0.0099 (8)	−0.0076 (8)
C4	0.0214 (12)	0.0197 (13)	0.0129 (11)	−0.0079 (10)	0.0054 (9)	−0.0020 (9)
C10	0.0142 (11)	0.0148 (12)	0.0133 (11)	−0.0002 (9)	0.0035 (9)	0.0004 (9)
C12	0.0159 (11)	0.0174 (12)	0.0194 (12)	−0.0053 (10)	0.0035 (10)	−0.0034 (10)
C13	0.0156 (11)	0.0175 (12)	0.0131 (11)	−0.0010 (10)	0.0042 (9)	−0.0008 (9)
C7	0.0107 (10)	0.0150 (12)	0.0183 (12)	−0.0017 (9)	0.0005 (9)	−0.0014 (9)
C3	0.0218 (12)	0.0174 (13)	0.0187 (12)	−0.0033 (10)	−0.0010 (10)	0.0011 (10)
C5	0.0163 (11)	0.0194 (13)	0.0199 (12)	−0.0019 (10)	0.0038 (10)	−0.0031 (10)
C1	0.0172 (11)	0.0185 (12)	0.0155 (12)	−0.0089 (10)	0.0054 (9)	−0.0043 (10)
C8	0.0157 (11)	0.0181 (12)	0.0140 (11)	−0.0012 (10)	0.0015 (9)	−0.0033 (9)
C11	0.0156 (11)	0.0163 (12)	0.0163 (11)	−0.0001 (10)	0.0023 (9)	−0.0042 (9)
C2	0.0146 (11)	0.0162 (12)	0.0232 (13)	−0.0027 (10)	0.0024 (10)	−0.0065 (10)
C17	0.0177 (11)	0.0213 (13)	0.0146 (11)	−0.0040 (10)	0.0050 (9)	−0.0028 (10)
C6	0.0204 (12)	0.0171 (12)	0.0176 (12)	−0.0038 (10)	0.0012 (10)	0.0029 (10)
C15	0.0201 (12)	0.0158 (12)	0.0162 (12)	−0.0058 (10)	0.0034 (10)	−0.0017 (9)
C16	0.0193 (12)	0.0185 (13)	0.0173 (12)	−0.0060 (10)	0.0054 (10)	−0.0031 (10)
C18	0.0167 (11)	0.0202 (13)	0.0185 (12)	−0.0050 (10)	0.0067 (10)	−0.0030 (10)
C9	0.0150 (11)	0.0157 (12)	0.0143 (11)	−0.0001 (9)	0.0021 (9)	−0.0007 (9)
C19	0.0176 (11)	0.0201 (13)	0.0167 (12)	−0.0038 (10)	0.0064 (10)	−0.0036 (10)
C23	0.0184 (12)	0.0169 (12)	0.0203 (13)	−0.0034 (10)	0.0068 (10)	−0.0032 (10)
C20	0.0148 (11)	0.0191 (13)	0.0213 (13)	−0.0045 (10)	0.0059 (10)	−0.0038 (10)
C14	0.0224 (12)	0.0167 (12)	0.0161 (12)	−0.0056 (10)	0.0055 (10)	−0.0047 (10)
C21	0.0173 (11)	0.0181 (13)	0.0194 (12)	−0.0046 (10)	0.0071 (10)	−0.0037 (10)
C25	0.0227 (13)	0.0212 (13)	0.0208 (13)	−0.0072 (11)	0.0102 (10)	−0.0039 (10)
C24	0.0183 (12)	0.0188 (13)	0.0197 (12)	−0.0054 (10)	0.0058 (10)	−0.0041 (10)
C22	0.0182 (12)	0.0194 (13)	0.0189 (12)	−0.0050 (10)	0.0064 (10)	−0.0040 (10)
C26	0.0307 (15)	0.0310 (16)	0.0262 (14)	−0.0122 (13)	0.0154 (12)	−0.0054 (12)

Geometric parameters (Å, º) top

Br1—C4	1.902 (2)	C15—H15	0.9300
Cl1—C2	1.724 (3)	C16—H16A	0.9700
O2—C7	1.201 (3)	C16—H16B	0.9700
O3—C13	1.361 (3)	C18—C19	1.527 (3)
O3—C16	1.435 (3)	C18—H18A	0.9700
O1—C7	1.370 (3)	C18—H18B	0.9700
O1—C1	1.392 (3)	C9—H9	0.9300
C4—C5	1.376 (4)	C19—C20	1.525 (3)
C4—C3	1.381 (4)	C19—H19A	0.9700
C10—C11	1.395 (3)	C19—H19B	0.9700
C10—C15	1.402 (3)	C23—C24	1.524 (3)
C10—C9	1.456 (3)	C23—C22	1.529 (3)
C12—C13	1.388 (4)	C23—H23A	0.9700
C12—C11	1.393 (3)	C23—H23B	0.9700
C12—H12	0.9300	C20—C21	1.529 (3)
C13—C14	1.401 (3)	C20—H20A	0.9700
C7—C8	1.464 (3)	C20—H20B	0.9700
C3—C2	1.391 (4)	C14—H14	0.9300
C3—H3	0.9300	C21—C22	1.519 (3)
C5—C6	1.393 (3)	C21—H21A	0.9700
C5—H5	0.9300	C21—H21B	0.9700
C1—C6	1.383 (4)	C25—C24	1.523 (3)
C1—C2	1.383 (4)	C25—C26	1.526 (4)
C8—C9	1.339 (3)	C25—H25A	0.9700
C8—H8	0.9300	C25—H25B	0.9700
C11—H11	0.9300	C24—H24A	0.9700
C17—C16	1.510 (3)	C24—H24B	0.9700
C17—C18	1.521 (3)	C22—H22A	0.9700
C17—H17A	0.9700	C22—H22B	0.9700
C17—H17B	0.9700	C26—H26A	0.9600
C6—H6	0.9300	C26—H26B	0.9600
C15—C14	1.380 (3)	C26—H26C	0.9600

C13—O3—C16	117.9 (2)	C19—C18—H18B	109.3
C7—O1—C1	116.30 (19)	H18A—C18—H18B	107.9
C5—C4—C3	122.6 (2)	C8—C9—C10	128.5 (2)
C5—C4—Br1	118.51 (19)	C8—C9—H9	115.7
C3—C4—Br1	118.9 (2)	C10—C9—H9	115.7
C11—C10—C15	118.0 (2)	C20—C19—C18	114.1 (2)
C11—C10—C9	118.2 (2)	C20—C19—H19A	108.7
C15—C10—C9	123.8 (2)	C18—C19—H19A	108.7
C13—C12—C11	119.1 (2)	C20—C19—H19B	108.7
C13—C12—H12	120.5	C18—C19—H19B	108.7
C11—C12—H12	120.5	H19A—C19—H19B	107.6
O3—C13—C12	124.5 (2)	C24—C23—C22	113.6 (2)
O3—C13—C14	115.6 (2)	C24—C23—H23A	108.8
C12—C13—C14	119.8 (2)	C22—C23—H23A	108.8
O2—C7—O1	121.8 (2)	C24—C23—H23B	108.8
O2—C7—C8	127.6 (2)	C22—C23—H23B	108.8
O1—C7—C8	110.5 (2)	H23A—C23—H23B	107.7
C4—C3—C2	118.1 (2)	C19—C20—C21	112.8 (2)
C4—C3—H3	120.9	C19—C20—H20A	109.0
C2—C3—H3	120.9	C21—C20—H20A	109.0
C4—C5—C6	118.8 (2)	C19—C20—H20B	109.0
C4—C5—H5	120.6	C21—C20—H20B	109.0
C6—C5—H5	120.6	H20A—C20—H20B	107.8
C6—C1—C2	120.9 (2)	C15—C14—C13	120.4 (2)
C6—C1—O1	120.4 (2)	C15—C14—H14	119.8
C2—C1—O1	118.7 (2)	C13—C14—H14	119.8
C9—C8—C7	118.1 (2)	C22—C21—C20	113.7 (2)
C9—C8—H8	120.9	C22—C21—H21A	108.8
C7—C8—H8	120.9	C20—C21—H21A	108.8
C12—C11—C10	121.9 (2)	C22—C21—H21B	108.8
C12—C11—H11	119.0	C20—C21—H21B	108.8
C10—C11—H11	119.0	H21A—C21—H21B	107.7
C1—C2—C3	120.2 (2)	C24—C25—C26	112.6 (2)
C1—C2—Cl1	120.1 (2)	C24—C25—H25A	109.1
C3—C2—Cl1	119.8 (2)	C26—C25—H25A	109.1
C16—C17—C18	112.7 (2)	C24—C25—H25B	109.1
C16—C17—H17A	109.1	C26—C25—H25B	109.1
C18—C17—H17A	109.1	H25A—C25—H25B	107.8
C16—C17—H17B	109.1	C25—C24—C23	112.9 (2)
C18—C17—H17B	109.1	C25—C24—H24A	109.0
H17A—C17—H17B	107.8	C23—C24—H24A	109.0
C1—C6—C5	119.5 (2)	C25—C24—H24B	109.0
C1—C6—H6	120.3	C23—C24—H24B	109.0
C5—C6—H6	120.3	H24A—C24—H24B	107.8
C14—C15—C10	120.8 (2)	C21—C22—C23	113.3 (2)
C14—C15—H15	119.6	C21—C22—H22A	108.9
C10—C15—H15	119.6	C23—C22—H22A	108.9
O3—C16—C17	106.8 (2)	C21—C22—H22B	108.9
O3—C16—H16A	110.4	C23—C22—H22B	108.9
C17—C16—H16A	110.4	H22A—C22—H22B	107.7
O3—C16—H16B	110.4	C25—C26—H26A	109.5
C17—C16—H16B	110.4	C25—C26—H26B	109.5
H16A—C16—H16B	108.6	H26A—C26—H26B	109.5
C17—C18—C19	111.7 (2)	C25—C26—H26C	109.5
C17—C18—H18A	109.3	H26A—C26—H26C	109.5
C19—C18—H18A	109.3	H26B—C26—H26C	109.5
C17—C18—H18B	109.3

C16—O3—C13—C12	−3.1 (4)	C4—C3—C2—Cl1	179.0 (2)
C16—O3—C13—C14	177.7 (2)	C2—C1—C6—C5	−1.5 (4)
C11—C12—C13—O3	−178.6 (2)	O1—C1—C6—C5	175.5 (2)
C11—C12—C13—C14	0.5 (4)	C4—C5—C6—C1	−0.2 (4)
C1—O1—C7—O2	−5.4 (4)	C11—C10—C15—C14	0.4 (4)
C1—O1—C7—C8	173.1 (2)	C9—C10—C15—C14	−177.4 (2)
C5—C4—C3—C2	−1.4 (4)	C13—O3—C16—C17	177.4 (2)
Br1—C4—C3—C2	178.0 (2)	C18—C17—C16—O3	175.7 (2)
C3—C4—C5—C6	1.7 (4)	C16—C17—C18—C19	177.7 (2)
Br1—C4—C5—C6	−177.7 (2)	C7—C8—C9—C10	174.4 (2)
C7—O1—C1—C6	78.9 (3)	C11—C10—C9—C8	175.9 (3)
C7—O1—C1—C2	−104.1 (3)	C15—C10—C9—C8	−6.3 (4)
O2—C7—C8—C9	10.5 (4)	C17—C18—C19—C20	176.0 (2)
O1—C7—C8—C9	−167.9 (2)	C18—C19—C20—C21	−179.6 (2)
C13—C12—C11—C10	−1.6 (4)	C10—C15—C14—C13	−1.4 (4)
C15—C10—C11—C12	1.1 (4)	O3—C13—C14—C15	−179.9 (2)
C9—C10—C11—C12	179.0 (2)	C12—C13—C14—C15	0.9 (4)
C6—C1—C2—C3	1.8 (4)	C19—C20—C21—C22	179.9 (2)
O1—C1—C2—C3	−175.3 (2)	C26—C25—C24—C23	−179.4 (2)
C6—C1—C2—Cl1	−177.6 (2)	C22—C23—C24—C25	179.3 (2)
O1—C1—C2—Cl1	5.4 (3)	C20—C21—C22—C23	179.4 (2)
C4—C3—C2—C1	−0.3 (4)	C24—C23—C22—C21	179.6 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2ⁱ	0.93	2.35	3.248 (3)	164
C16—H16A···Cg2ⁱⁱ	0.97	2.95	3.824 (3)	150

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

Acknowledgements

The authors acknowledge the Raman Research Institute, Bangalore, and Center of Innovative Science, Engineering and Education (CISEE), UCS, Tumkur University for constant support in extending the laboratory facilities. MHK is thankful to BSPM's lab for use of their computing facilities at the Department of PG Studies and Research in Physics, Tumkur University.

Funding information

Funding for this research was provided by: Vission Group of Science and Technology (award No. GRD319 to Palakshamurthy BS) .

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