In the title compound, the aromatic rings are oriented at a dihedral angle of 83.30 (2)°. An intramolecular C—H⋯O contact generates a five-membered S(5) ring motif. In the crystal, C—H⋯O hydrogen bonds link the molecules through R12(6), R22(10), R22(14) hydrogen-bond motifs.
Keywords: crystal structure, 4-bromo-2-chlorophenyl, Hirshfeld surface
Abstract
The asymmetric unit of the compound C20H20BrClO3 contains one independent molecule in which the aromatic rings are oriented at a dihedral angle of 83.30 (2)°. An intramolecular C—H⋯O contact generates a five-membered S(5) ring motif. In the crystal, C—H⋯O hydrogen bonds link the molecules through R12(6), R22(10), R22(14) hydrogen-bond motifs. The structure is consolidated by C—H⋯π interactions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (32.8%), C⋯H/H⋯C (28.1%), O⋯H/H⋯O (14.0%) Br⋯H/H⋯Br (12.5%) and Cl⋯H/H⋯Cl (10.6%) interactions.
1. Chemical context
4-Bromo-2-chlorophenyl derivatives possess an interesting in vitro inhibitory activity on plasmodium falciparum bacteria and serve as the starting molecule for structure-based design of novel inhibitors for anti-plasmodial and transmission-blocking agents (Vallone et al., 2018 ▸). These compounds are known to exhibit anti-malarial activity (Kos et al., 2022 ▸). Compounds having halogen atoms at the ortho and meta positions with respect to the bromine have also been found to exhibit anti-inflammatory activity (Hošek et al., 2019 ▸). This class of compounds are very important for the design of drugs for the treatment of diseases such as dengue and chikungunya and furthermore, the introduction of alkyl groups into these compounds will induce better penetration capacity at the cellular level. Compounds obtained by combining 4-bromo-2-chlorophenyl and (alkyloxy)phenyl-derived molecules are well known for their antimicrobial activity (Radwan et al., 2014 ▸) and antitumor properties (Jung et al., 2019 ▸; Pieters et al., 1999 ▸). The role of alkyl groups in the various drug molecules is to speed up the penetration of compounds into the cell i.e. into mitochondria. In this context, it is found that decylcaffeic acid inhibits the growth of colorectal cancer cells (Lukáč et al., 2024 ▸) and alkyl groups in cinnamic acid-based molecules encourage antituberculosis activity (De et al., 2011 ▸). The alkyl group, which makes an amido links with various aromatic or heterocyclic rigid cores, will enhance the degree of inhibition activity of anti-inflammatory drugs (Matta et al., 2020 ▸). Keeping these properties in mind, we decided to synthesize and study the title compound, which has both a rigid core (4-bromo-2-chlorophenyl) and an alkyloxy chain linked through the ester group and present the results herein.
2. Structural commentary
The title compound (Fig. 1 ▸) crystallizes in space group P
. The dihedral angle between the 4-bromo-2-chlorophenyl aromatic ring (C1–C6) and the aromatic ring of the pentyloxy phenyl fragment (C10–C15) is 83.30 (2)°. The torsion angles C1—O1—C7—C8 and C13—O3—C16—C17 are 175.98 (14) and −179.32 (14)°, respectively, which are anti-periplanar. The H8—C8=C9—H9 atoms exhibit an E-configuration with a torsion angle of 178° and the molecule is non planar with an r.m.s. deviation of 0.065 Å. An intramolecular hydrogen-bond interaction generates an S(5) motif (Fig. 2 ▸b).
Figure 1.
The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.
Figure 2.
The molecular packing of the title compound. Dashed lines indicate the C—H⋯O hydrogen-bonding interactions. The 
(6), 
(10) (a) and (14) (b) synthons are indicated by dotted pale-green lines and the S(5) ring is shown in pink (b).
3. Supramolecular features
In the crystal, C—H⋯O hydrogen bonds (Table 1 ▸, Fig. 2 ▸a) link the molecules through (6), (10) and (14) cyclic hydrogen-bond motifs (Bernstein et al., 1995 ▸), forming inversion dimers. Together these interactions generate molecular sheets parallel to (010). The inversion dimers are linked through weak C—H⋯Cl interactions (Table 1 ▸) as shown in Fig. 3 ▸. The packing is further consolidated by C—H⋯π interactions (Fig. 4 ▸, Table 1 ▸).
Table 1. Hydrogen-bond geometry (Å, °).
Cg1 and Cg2 are the centroids of the 4-bromo-2-chlorophenyl (C1–C6) and phenyl (C10–C15) rings, respectively.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C6—H6⋯Cl1i | 0.93 | 2.93 | 3.613 (2) | 131 |
| C9—H9⋯O2 | 0.93 | 2.50 | 2.848 (2) | 102 |
| C9—H9⋯O2ii | 0.93 | 2.46 | 3.291 (2) | 149 |
| C15—H15⋯O2ii | 0.93 | 2.58 | 3.371 (2) | 143 |
| C11—H11⋯Cg1iii | 0.93 | 2.76 | 3.5716 (18) | 147 |
| C16—H16B⋯Cg2iv | 0.97 | 2.79 | 3.6687 (17) | 151 |
| C18—H18B⋯Cg2v | 0.97 | 2.85 | 3.7194 (17) | 150 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
; (iv) 
; (v) 
.
Figure 3.
The molecular packing of the title compound with weak C—H⋯Cl interactions indicated by magenta coloured dashed lines.
Figure 4.
The molecular packing of the title compound. Dashed lines indicate the C—H⋯π interactions.
4. Hirshfeld surface analysis
Hirshfeld surface analysis (Hirshfeld, 1977 ▸; Spackman & Jayatilaka, 2009 ▸) was used to visualize and quantify intermolecular interactions using Crystal Explorer (Spackman et al., 2021 ▸). The two-dimensional fingerprint plots (Fig. 5 ▸) quantifying the various intermolecular interactions indicate that the major contributions to the crystal packing of the title molecule are from H⋯H (32.8%), C⋯ H/H ⋯C (28.1%), O⋯H/H⋯O (14.0%), Br⋯H/H⋯Br (12.5%) and Cl⋯H/H⋯Cl (10.6%) contacts.
Figure 5.
The two-dimensional fingerprint plots for the title compound, showing all interactions, and those delineated into H⋯H, C⋯H/H⋯C, O⋯H/H⋯O, Br⋯H/H⋯Br and Cl⋯H/H⋯Cl contacts.
5. Database survey
A search of the Cambridge Structural Database (CSD version 2.0.4, December 2019; Groom et al., 2016 ▸) for molecules containing the 4-bromo-2-chlorophenyl moiety resulted in 15 matches. Of these, the six compounds with CSD codes EBEPUZ (Lehmler et al., 2013 ▸), EJULUT (Dumitrescu et al., 2020 ▸), ISOJUX (Reddy et al., 2016 ▸), FANFOS (Sangeeta et al., 2017 ▸) and VIDQUX (Mohan et al., 2018 ▸) have either alkyloxy or substituted aromatic or heterocyclic rings connected fragments that are found to be in the same plane. The dihedral angle made by these planes with the 4-bromo-2-chlorophenyl moiety are 59.0, 75.3, 88.78, 37.47, and 2.99°, respectively, whereas in the title compound, the dihedral angle between the 4-bromo-2-chlorophenyl and (pentyloxy)phenylprop-2-enoate moieties is 82.15 (2)°. The torsion angle between the ortho-substituted chlorine atom and the first atom of the planar functional group in the above compounds is between 1 and 3° while in the title compound this torsion angle is 1.2 (2)°.
6. Synthesis and crystallization
A mixture of 4-bromo-2-chlorophenol (0.208 g, 0.001 mol) and (E)-3-[4-(pentyloxy)phenyl]acrylic acid (0.234 g, 0.001 mol) was suspended in anhydrous chloroform (10 ml). To this was added N,N-dicyclohexylcarbodiimide (0.206 g, 0.001 mol) and 4-N,N-dimethylamino pyridine (5 mg) 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 that was crystallized from a chloroform–petroleum ether mixture. Yield 75%. Elemental analysis calculated: C, 56.69; H, 4.76; Br, 18.86; Cl, 8.37; O, 11.33%; found: C, 56.71; H, 4.79; Cl, 8.42%, m.p. 371–373 K.
7. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. H atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C20H20BrClO3 |
| M r | 423.72 |
| Crystal system, space group | Triclinic, P
|
| Temperature (K) | 296 |
| a, b, c (Å) | 7.5850 (7), 9.825 (1), 12.8466 (13) |
| α, β, γ (°) | 87.176 (3), 85.069 (3), 82.934 (3) |
| V (Å3) | 945.85 (16) |
| Z | 2 |
| Radiation type | Mo Kα |
| μ (mm−1) | 2.33 |
| Crystal size (mm) | 0.32 × 0.27 × 0.24 |
| Data collection | |
| Diffractometer | Bruker SMART APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Krause et al., 2015 ▸) |
| Tmin, Tmax | 0.476, 0.570 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 14284, 4721, 4105 |
| R int | 0.035 |
| (sin θ/λ)max (Å−1) | 0.668 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.066, 1.03 |
| No. of reflections | 4721 |
| No. of parameters | 227 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.39, −0.45 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989025003317/vu2011sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989025003317/vu2011Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989025003317/vu2011Isup3.cml
CCDC reference: 2443273
Additional supporting information: crystallographic information; 3D view; checkCIF report
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors acknowledge the Raman Research Institute, Bangalore, and Centre of Innovative Science, Engineering and Education (CISEE), UCS, Tumkur University, for constant support in extending the laboratory facilities. MHK thankful to BSPM’s lab for use of their computing facilities at the Department of PG Studies and Research in Physics, Tumkur University.
supplementary crystallographic information
4-Bromo-2-chlorophenyl (2E)-3-[4-(pentyloxy)phenyl]prop-2-enoate . Crystal data
| C20H20BrClO3 | F(000) = 432 |
| Mr = 423.72 | Prism |
| Triclinic, P1 | Dx = 1.488 Mg m−3 |
| Hall symbol: -P 1 | Melting point: 458 K |
| a = 7.5850 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 9.825 (1) Å | Cell parameters from 4105 reflections |
| c = 12.8466 (13) Å | θ = 2.5–29.0° |
| α = 87.176 (3)° | µ = 2.33 mm−1 |
| β = 85.069 (3)° | T = 296 K |
| γ = 82.934 (3)° | Prism, colourless |
| V = 945.85 (16) Å3 | 0.32 × 0.27 × 0.24 mm |
| Z = 2 |
4-Bromo-2-chlorophenyl (2E)-3-[4-(pentyloxy)phenyl]prop-2-enoate . Data collection
| Bruker SMART APEXII CCD diffractometer | 4721 independent reflections |
| Radiation source: fine-focus sealed tube | 4105 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.035 |
| Detector resolution: 1.02 pixels mm-1 | θmax = 28.4°, θmin = 2.7° |
| φ and Ω scans | h = −10→10 |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −13→13 |
| Tmin = 0.476, Tmax = 0.570 | l = −17→17 |
| 14284 measured reflections |
4-Bromo-2-chlorophenyl (2E)-3-[4-(pentyloxy)phenyl]prop-2-enoate . Refinement
| 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)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.066 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.023P)2 + 0.4253P] where P = (Fo2 + 2Fc2)/3 |
| 4721 reflections | (Δ/σ)max = 0.004 |
| 227 parameters | Δρmax = 0.39 e Å−3 |
| 0 restraints | Δρmin = −0.45 e Å−3 |
| 0.123 constraints |
4-Bromo-2-chlorophenyl (2E)-3-[4-(pentyloxy)phenyl]prop-2-enoate . Special details
| 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. |
4-Bromo-2-chlorophenyl (2E)-3-[4-(pentyloxy)phenyl]prop-2-enoate . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Br1 | 0.18439 (3) | 0.12617 (2) | 1.03966 (2) | 0.02099 (6) | |
| Cl1 | 0.69315 (6) | 0.12132 (7) | 0.70527 (4) | 0.03690 (13) | |
| O3 | 0.78618 (16) | 0.38029 (12) | −0.06342 (9) | 0.0169 (2) | |
| O1 | 0.38962 (16) | 0.12409 (12) | 0.57472 (9) | 0.0169 (2) | |
| O2 | 0.3931 (2) | 0.35324 (13) | 0.57369 (10) | 0.0260 (3) | |
| C4 | 0.2485 (2) | 0.12778 (16) | 0.89331 (13) | 0.0159 (3) | |
| C10 | 0.5853 (2) | 0.35279 (16) | 0.24860 (12) | 0.0134 (3) | |
| C12 | 0.6902 (2) | 0.24985 (17) | 0.08324 (13) | 0.0154 (3) | |
| H12 | 0.716007 | 0.172269 | 0.043468 | 0.018* | |
| C8 | 0.4799 (2) | 0.23374 (17) | 0.41618 (13) | 0.0151 (3) | |
| H8 | 0.492031 | 0.148155 | 0.386742 | 0.018* | |
| C7 | 0.4187 (2) | 0.24945 (17) | 0.52630 (13) | 0.0155 (3) | |
| C11 | 0.6237 (2) | 0.23732 (17) | 0.18630 (13) | 0.0155 (3) | |
| H11 | 0.604072 | 0.151208 | 0.214998 | 0.019* | |
| C13 | 0.7190 (2) | 0.37875 (17) | 0.03838 (12) | 0.0140 (3) | |
| C9 | 0.5182 (2) | 0.34530 (17) | 0.35835 (13) | 0.0147 (3) | |
| H9 | 0.499875 | 0.427875 | 0.392337 | 0.018* | |
| C1 | 0.3422 (2) | 0.12854 (16) | 0.68166 (13) | 0.0147 (3) | |
| C5 | 0.1161 (2) | 0.12990 (18) | 0.82517 (14) | 0.0202 (4) | |
| H5 | −0.002839 | 0.131054 | 0.850218 | 0.024* | |
| C3 | 0.4258 (2) | 0.12611 (17) | 0.85862 (13) | 0.0184 (3) | |
| H3 | 0.512420 | 0.124852 | 0.905778 | 0.022* | |
| C15 | 0.6154 (2) | 0.48017 (17) | 0.20237 (13) | 0.0154 (3) | |
| H15 | 0.590935 | 0.557698 | 0.242285 | 0.018* | |
| C14 | 0.6808 (2) | 0.49489 (17) | 0.09858 (13) | 0.0156 (3) | |
| H14 | 0.699023 | 0.581115 | 0.069501 | 0.019* | |
| C17 | 0.8891 (2) | 0.49610 (18) | −0.22259 (13) | 0.0180 (3) | |
| H17A | 0.802673 | 0.458591 | −0.260963 | 0.022* | |
| H17B | 0.997676 | 0.432518 | −0.225787 | 0.022* | |
| C18 | 0.9276 (2) | 0.63480 (18) | −0.27262 (13) | 0.0186 (3) | |
| H18A | 0.819067 | 0.698353 | −0.266778 | 0.022* | |
| H18B | 1.014894 | 0.670824 | −0.234011 | 0.022* | |
| C2 | 0.4721 (2) | 0.12635 (18) | 0.75163 (14) | 0.0176 (3) | |
| C16 | 0.8173 (2) | 0.51254 (17) | −0.11028 (13) | 0.0159 (3) | |
| H16A | 0.902213 | 0.552149 | −0.072138 | 0.019* | |
| H16B | 0.706771 | 0.573970 | −0.107005 | 0.019* | |
| C6 | 0.1655 (2) | 0.13025 (18) | 0.71820 (14) | 0.0200 (4) | |
| H6 | 0.078790 | 0.131658 | 0.671066 | 0.024* | |
| C19 | 0.9971 (3) | 0.6278 (2) | −0.38731 (14) | 0.0263 (4) | |
| H19A | 1.108096 | 0.567089 | −0.393177 | 0.032* | |
| H19B | 0.911805 | 0.589191 | −0.425798 | 0.032* | |
| C20 | 1.0284 (3) | 0.7680 (3) | −0.43626 (17) | 0.0380 (6) | |
| H20A | 1.074526 | 0.758169 | −0.507796 | 0.057* | |
| H20B | 1.112534 | 0.806870 | −0.398383 | 0.057* | |
| H20C | 0.917802 | 0.827400 | −0.433463 | 0.057* |
4-Bromo-2-chlorophenyl (2E)-3-[4-(pentyloxy)phenyl]prop-2-enoate . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.02982 (11) | 0.01924 (9) | 0.01305 (9) | −0.00280 (7) | 0.00343 (6) | −0.00147 (6) |
| Cl1 | 0.0158 (2) | 0.0705 (4) | 0.0242 (3) | −0.0090 (2) | 0.00258 (18) | 0.0020 (2) |
| O3 | 0.0247 (7) | 0.0142 (6) | 0.0112 (6) | −0.0028 (5) | 0.0034 (5) | −0.0005 (4) |
| O1 | 0.0242 (6) | 0.0139 (6) | 0.0123 (6) | −0.0038 (5) | 0.0028 (5) | 0.0001 (4) |
| O2 | 0.0471 (9) | 0.0141 (6) | 0.0165 (6) | −0.0068 (6) | 0.0047 (6) | −0.0028 (5) |
| C4 | 0.0220 (9) | 0.0108 (8) | 0.0141 (8) | −0.0016 (6) | 0.0028 (6) | −0.0003 (6) |
| C10 | 0.0129 (8) | 0.0148 (8) | 0.0125 (8) | −0.0018 (6) | −0.0020 (6) | 0.0005 (6) |
| C12 | 0.0177 (8) | 0.0135 (8) | 0.0149 (8) | −0.0010 (6) | −0.0008 (6) | −0.0026 (6) |
| C8 | 0.0171 (8) | 0.0142 (8) | 0.0139 (8) | −0.0019 (6) | 0.0011 (6) | −0.0027 (6) |
| C7 | 0.0173 (8) | 0.0147 (8) | 0.0142 (8) | −0.0033 (6) | −0.0002 (6) | 0.0022 (6) |
| C11 | 0.0170 (8) | 0.0128 (8) | 0.0166 (8) | −0.0031 (6) | −0.0006 (6) | 0.0012 (6) |
| C13 | 0.0145 (8) | 0.0161 (8) | 0.0111 (8) | −0.0018 (6) | −0.0006 (6) | 0.0000 (6) |
| C9 | 0.0150 (8) | 0.0158 (8) | 0.0135 (8) | −0.0015 (6) | −0.0010 (6) | −0.0019 (6) |
| C1 | 0.0206 (8) | 0.0103 (7) | 0.0125 (8) | −0.0015 (6) | 0.0012 (6) | 0.0009 (6) |
| C5 | 0.0162 (8) | 0.0247 (9) | 0.0186 (9) | −0.0022 (7) | 0.0024 (7) | 0.0028 (7) |
| C3 | 0.0190 (9) | 0.0205 (9) | 0.0162 (8) | −0.0041 (7) | −0.0024 (7) | −0.0006 (6) |
| C15 | 0.0189 (8) | 0.0128 (8) | 0.0147 (8) | −0.0025 (6) | −0.0003 (6) | −0.0034 (6) |
| C14 | 0.0192 (8) | 0.0126 (8) | 0.0147 (8) | −0.0024 (6) | −0.0001 (6) | 0.0010 (6) |
| C17 | 0.0189 (8) | 0.0211 (9) | 0.0131 (8) | −0.0006 (7) | 0.0011 (6) | −0.0013 (6) |
| C18 | 0.0171 (8) | 0.0236 (9) | 0.0144 (8) | −0.0022 (7) | 0.0002 (6) | 0.0022 (6) |
| C2 | 0.0146 (8) | 0.0197 (9) | 0.0184 (9) | −0.0043 (6) | 0.0019 (6) | −0.0003 (6) |
| C16 | 0.0184 (8) | 0.0151 (8) | 0.0138 (8) | −0.0025 (6) | 0.0012 (6) | 0.0006 (6) |
| C6 | 0.0180 (8) | 0.0253 (9) | 0.0167 (9) | −0.0033 (7) | −0.0021 (7) | 0.0021 (7) |
| C19 | 0.0214 (9) | 0.0406 (12) | 0.0145 (9) | 0.0012 (8) | 0.0016 (7) | 0.0044 (8) |
| C20 | 0.0250 (11) | 0.0560 (15) | 0.0298 (12) | −0.0034 (10) | 0.0016 (9) | 0.0219 (10) |
4-Bromo-2-chlorophenyl (2E)-3-[4-(pentyloxy)phenyl]prop-2-enoate . Geometric parameters (Å, º)
| Br1—C4 | 1.9009 (16) | C5—C6 | 1.393 (2) |
| Cl1—C2 | 1.7263 (17) | C5—H5 | 0.9300 |
| O3—C13 | 1.3623 (18) | C3—C2 | 1.389 (2) |
| O3—C16 | 1.4424 (19) | C3—H3 | 0.9300 |
| O1—C7 | 1.3858 (19) | C15—C14 | 1.389 (2) |
| O1—C1 | 1.3914 (19) | C15—H15 | 0.9300 |
| O2—C7 | 1.200 (2) | C14—H14 | 0.9300 |
| C4—C3 | 1.378 (2) | C17—C16 | 1.507 (2) |
| C4—C5 | 1.385 (3) | C17—C18 | 1.528 (2) |
| C10—C15 | 1.395 (2) | C17—H17A | 0.9700 |
| C10—C11 | 1.407 (2) | C17—H17B | 0.9700 |
| C10—C9 | 1.459 (2) | C18—C19 | 1.523 (2) |
| C12—C11 | 1.381 (2) | C18—H18A | 0.9700 |
| C12—C13 | 1.399 (2) | C18—H18B | 0.9700 |
| C12—H12 | 0.9300 | C16—H16A | 0.9700 |
| C8—C9 | 1.341 (2) | C16—H16B | 0.9700 |
| C8—C7 | 1.460 (2) | C6—H6 | 0.9300 |
| C8—H8 | 0.9300 | C19—C20 | 1.523 (3) |
| C11—H11 | 0.9300 | C19—H19A | 0.9700 |
| C13—C14 | 1.397 (2) | C19—H19B | 0.9700 |
| C9—H9 | 0.9300 | C20—H20A | 0.9600 |
| C1—C6 | 1.380 (2) | C20—H20B | 0.9600 |
| C1—C2 | 1.387 (2) | C20—H20C | 0.9600 |
| C13—O3—C16 | 116.35 (12) | C15—C14—C13 | 119.26 (15) |
| C7—O1—C1 | 114.71 (13) | C15—C14—H14 | 120.4 |
| C3—C4—C5 | 122.21 (16) | C13—C14—H14 | 120.4 |
| C3—C4—Br1 | 118.70 (13) | C16—C17—C18 | 110.16 (14) |
| C5—C4—Br1 | 119.09 (13) | C16—C17—H17A | 109.6 |
| C15—C10—C11 | 117.68 (15) | C18—C17—H17A | 109.6 |
| C15—C10—C9 | 118.90 (15) | C16—C17—H17B | 109.6 |
| C11—C10—C9 | 123.42 (14) | C18—C17—H17B | 109.6 |
| C11—C12—C13 | 120.30 (15) | H17A—C17—H17B | 108.1 |
| C11—C12—H12 | 119.8 | C19—C18—C17 | 113.57 (15) |
| C13—C12—H12 | 119.8 | C19—C18—H18A | 108.9 |
| C9—C8—C7 | 118.63 (15) | C17—C18—H18A | 108.9 |
| C9—C8—H8 | 120.7 | C19—C18—H18B | 108.9 |
| C7—C8—H8 | 120.7 | C17—C18—H18B | 108.9 |
| O2—C7—O1 | 121.15 (15) | H18A—C18—H18B | 107.7 |
| O2—C7—O1 | 121.15 (15) | C1—C2—C3 | 120.49 (15) |
| O2—C7—C8 | 127.83 (15) | C1—C2—Cl1 | 119.66 (13) |
| O2—C7—C8 | 127.83 (15) | C3—C2—Cl1 | 119.84 (14) |
| O1—C7—C8 | 111.02 (14) | O3—C16—C17 | 109.47 (13) |
| C12—C11—C10 | 121.05 (15) | O3—C16—H16A | 109.8 |
| C12—C11—H11 | 119.5 | C17—C16—H16A | 109.8 |
| C10—C11—H11 | 119.5 | O3—C16—H16B | 109.8 |
| O3—C13—C14 | 124.48 (14) | C17—C16—H16B | 109.8 |
| O3—C13—C12 | 115.88 (14) | H16A—C16—H16B | 108.2 |
| C14—C13—C12 | 119.64 (15) | C1—C6—C5 | 120.49 (17) |
| C8—C9—C10 | 127.86 (16) | C1—C6—H6 | 119.8 |
| C8—C9—H9 | 116.1 | C5—C6—H6 | 119.8 |
| C10—C9—H9 | 116.1 | C20—C19—C18 | 112.52 (18) |
| C6—C1—C2 | 119.99 (15) | C20—C19—H19A | 109.1 |
| C6—C1—O1 | 119.64 (15) | C18—C19—H19A | 109.1 |
| C2—C1—O1 | 120.32 (15) | C20—C19—H19B | 109.1 |
| C4—C5—C6 | 118.32 (16) | C18—C19—H19B | 109.1 |
| C4—C5—H5 | 120.8 | H19A—C19—H19B | 107.8 |
| C6—C5—H5 | 120.8 | C19—C20—H20A | 109.5 |
| C4—C3—C2 | 118.49 (16) | C19—C20—H20B | 109.5 |
| C4—C3—H3 | 120.8 | H20A—C20—H20B | 109.5 |
| C2—C3—H3 | 120.8 | C19—C20—H20C | 109.5 |
| C14—C15—C10 | 122.07 (15) | H20A—C20—H20C | 109.5 |
| C14—C15—H15 | 119.0 | H20B—C20—H20C | 109.5 |
| C10—C15—H15 | 119.0 | ||
| C1—O1—C7—O2 | −4.4 (2) | C5—C4—C3—C2 | −0.1 (3) |
| C1—O1—C7—O2 | −4.4 (2) | Br1—C4—C3—C2 | 179.57 (12) |
| C1—O1—C7—C8 | 175.98 (14) | C11—C10—C15—C14 | 0.1 (2) |
| C9—C8—C7—O2 | 1.9 (3) | C9—C10—C15—C14 | 179.33 (16) |
| C9—C8—C7—O2 | 1.9 (3) | C10—C15—C14—C13 | −0.4 (3) |
| C9—C8—C7—O1 | −178.50 (15) | O3—C13—C14—C15 | −178.89 (15) |
| C13—C12—C11—C10 | −0.7 (3) | C12—C13—C14—C15 | 0.2 (3) |
| C15—C10—C11—C12 | 0.5 (2) | C16—C17—C18—C19 | −178.75 (15) |
| C9—C10—C11—C12 | −178.75 (15) | C6—C1—C2—C3 | −0.1 (3) |
| C16—O3—C13—C14 | −0.5 (2) | O1—C1—C2—C3 | −177.82 (15) |
| C16—O3—C13—C12 | −179.66 (14) | C6—C1—C2—Cl1 | 178.92 (13) |
| C11—C12—C13—O3 | 179.49 (15) | O1—C1—C2—Cl1 | 1.2 (2) |
| C11—C12—C13—C14 | 0.3 (3) | C4—C3—C2—C1 | 0.1 (3) |
| C7—C8—C9—C10 | 178.25 (16) | C4—C3—C2—Cl1 | −178.89 (13) |
| C15—C10—C9—C8 | 179.46 (17) | C13—O3—C16—C17 | −179.32 (14) |
| C11—C10—C9—C8 | −1.3 (3) | C18—C17—C16—O3 | −178.46 (14) |
| C7—O1—C1—C6 | 100.14 (18) | O1—C1—C6—C5 | 177.77 (15) |
| C7—O1—C1—C2 | −82.15 (19) | C17—C18—C19—C20 | 178.03 (16) |
| Br1—C4—C5—C6 | −179.64 (13) |
4-Bromo-2-chlorophenyl (2E)-3-[4-(pentyloxy)phenyl]prop-2-enoate . Hydrogen-bond geometry (Å, º)
Cg1 and Cg2 are the centroids of the 4-bromo-2-chlorophenyl (C1–C6) and phenyl (C10–C15) rings, respectively.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C6—H6···Cl1i | 0.93 | 2.93 | 3.613 (2) | 131 |
| C9—H9···O2 | 0.93 | 2.50 | 2.848 (2) | 102 |
| C9—H9···O2ii | 0.93 | 2.46 | 3.291 (2) | 149 |
| C15—H15···O2ii | 0.93 | 2.58 | 3.371 (2) | 143 |
| C11—H11···Cg1iii | 0.93 | 2.76 | 3.5716 (18) | 147 |
| C16—H16B···Cg2iv | 0.97 | 2.79 | 3.6687 (17) | 151 |
| C18—H18B···Cg2v | 0.97 | 2.85 | 3.7194 (17) | 150 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1; (iv) −x+1, −y+1, −z; (v) −x+2, −y+1, −z.
Funding Statement
Funding for this research was provided by: Vission Group of Science and Technology (award No. GRD319 to B. S. Palakshamurthy).
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989025003317/vu2011sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989025003317/vu2011Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989025003317/vu2011Isup3.cml
CCDC reference: 2443273
Additional supporting information: crystallographic information; 3D view; checkCIF report
Additional supporting information: crystallographic information; 3D view; checkCIF report