Crystal structure and Hirshfeld surface analysis of (2E)-1-(4-bromo­phen­yl)-3-(2-methyl­phen­yl)prop-2-en-1-one

Akkurt, M.; Naghiyev, F.N.; Khrustalev, V.N.; Asadov, K.A.; Khalilov, A.N.; Bhattarai, A.; Mamedov, İ.G.

doi:10.1107/S2056989023007387

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ISSN: 2056-9890

Volume 79| Part 9| September 2023| Pages 847-851

https://doi.org/10.1107/S2056989023007387

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Crystal structure and Hirshfeld surface analysis of (2E)-1-(4-bromophenyl)-3-(2-methylphenyl)prop-2-en-1-one

Mehmet Akkurt,^a Farid N. Naghiyev,^b Victor N. Khrustalev,^c,^d Khammed A. Asadov,^b Ali N. Khalilov,^e,^b Ajaya Bhattarai ^f ^* and İbrahim G. Mamedov ^b

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, ^bDepartment of Chemistry, Baku State University, Z. Khalilov str. 23, AZ1148, Baku, Azerbaijan, ^cPeoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St. 6, Moscow 117198, Russian Federation, ^dN. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation, ^e`Composite Materials' Scientific Research Center, Azerbaijan State Economic University (UNEC), H. Aliyev str. 135, AZ1063, Baku, Azerbaijan, and ^fDepartment of Chemistry, M.M.A.M.C. (Tribhuvan University) Biratnagar, Nepal
^*Correspondence e-mail: ajaya.bhattarai@mmamc.tu.edu.np

Edited by B. Therrien, University of Neuchâtel, Switzerland (Received 14 August 2023; accepted 22 August 2023; online 30 August 2023)

In the title compound, C₁₆H₁₃BrO, the planes of the aromatic rings are inclined at an angle of 23.49 (15)°, and the configuration about the C=C bond is E. In the crystal, the molecules are linked into chains by weak C—H⋯O interactions along the b axis. Successive chains form a zigzag structure along the c axis, and these chains are connected to each other by face-to-face π–π stacking interactions along the a axis. These layers, parallel to the (001) plane, are linked by van der Waals interactions, thus consolidating the crystal structure. Hirshfeld surface analysis showed that the most significant contacts in the structure are H⋯H (43.1%), C⋯H/H⋯C (17.4%), Br⋯H/H⋯Br (14.9%), C⋯C (11.9%) and O⋯H/H⋯O (9.8%).

Keywords: crystal structure; E configuration; weak C—H⋯O interactions; face-to-face π–π stacking interactions; Hirshfeld surface analysis.

CCDC reference: 2290092

1. Chemical context

Diverse C—C, C—N, C—S and C—O bond formations are fundamental and valuable conversions in modern organic chemistry (Gurbanov et al., 2017 ; Afkhami et al., 2019 ; Mahmoudi et al., 2021 ). Chalcones are α,β-unsaturated ketones containing aryl–aryl or aryl–alkyl groups at both ends. They belong to the flavonoid family, and they possess a wide variety of biological activities. Many natural chalcones, such as echinatin, naringenin, isoliquiritigenin, butein, 4-hydroxyderricin, 4-hydroxylonchocarpin, derricin, xanthoangelol, lonchocarpin, licochalcone A, licochalcone E, humulusol, munsericin, flavokawain A, isobavachalcone, mallotophilippen C, D and E, broussochalcone A, crotaorixin, pedicinin and nardoaristolone A have been isolated from plants (Rozmer & Perjési, 2016 ; Çelik et al., 2023 ; Chalkha et al., 2023 ). Moreover, the enone moiety is a widespread structural motif often found in biologically active compounds possessing enzyme inhibitory, anticancer and antimicrobial activity (Poustforoosh et al., 2022 ; Tapera et al., 2022 ; Sarkı et al., 2023 ). Herein, in continuation to our recent investigations (Gurbanov et al., 2022a ,b ), we report the crystal structure and Hirshfeld surface analysis of (2E)-1-(4-bromophenyl)-3-(2-methylphenyl)prop-2-en-1-one.

2. Structural commentary

The title compound (Fig. 1) is composed of two aromatic rings, i.e. 2-methylphenyl (C4–C9) and 4-bromophenyl (C11–C16), which are linked by a –CO—CH=CH– E-configured enone bridge. The molecule is approximately planar, as indicated by the torsion angles C10—C5—C4—C3 = 1.9 (5)°, C9—C4—C3—C2 = −4.4 (5)°, C4—C3—C2—C1 = −176.3 (3)°, C3—C2—C1—C11 = −168.2 (3)°, C2—C1—C11—C12 = 15.9 (4)° and Br1—C14—C15—C16 = 178.5 (2)°. The dihedral angle between the planes of the 2-methylphenyl and 4-bromophenyl rings is 23.49 (15)°.

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 and Hirshfeld surface analysis

In the crystal, the molecules are linked into C(5) chains (Bernstein et al., 1995 ) by weak C—H⋯O interactions (Table 1 and Fig. 2) along the a axis. Successive chains form a zigzag structure along the b axis (Fig. 3) and these chains are connected to each other along the c axis by face-to-face π–π stacking interactions [Cg1⋯Cg1^a = 3.942 (2) Å, slippage = 1.890 Å; Cg2⋯Cg2^a = 3.9420 (18) Å, slippage = 1.942 Å; symmetry code: (a) x − 1, y, z; Cg1 and Cg2 are the centroids of the 2-methylphenyl (C4—C9) and 4-bromophenyl (C11–C16) rings, respectively]. They form layers parallel to the (001) plane through van der Waals interactions, thus consolidating the crystal structure.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.95	2.58	3.200 (3)	124
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
View of the C—H⋯O hydrogen bonds and face-to-face π–π stacking interactions in the title compound along the c axis.

Figure 3
Zigzag packing of the title compound along the b axis.

CrystalExplorer17.5 (Spackman et al., 2021 ) was used to compute the Hirshfeld surfaces and the two-dimensional fingerprints of the title molecule. The d_norm mappings for the title compound were performed in the range from −0.0627 to +1.1373 a.u., on the d_norm surfaces, allowing the location of the C—H⋯O interactions (Tables 1 and 2).

Table 2
Summary of short interatomic contacts (Å) in the title compound

C3⋯H10B	2.85	x + 1, y, z
Br1⋯H7	3.17	−x + $[{3\over 2}]$ , −y + 1, z − $[{1\over 2}]$
O1⋯H12	2.58	−x + 1, y + $[{1\over 2}]$ , −z + $[{1\over 2}]$
H15⋯H9	2.45	−x + 2, y + $[{1\over 2}]$ , −z + $[{1\over 2}]$
C10⋯H10A	3.10	x + $[{1\over 2}]$ , −y + $[{3\over 2}]$ , −z + 1

The fingerprint plots (Fig. 4) show that H⋯H [Fig. 4(b); 43.1%], C⋯H/H⋯C [Fig. 4(c); 17.4%], Br⋯H/H⋯Br [Fig. 4(d); 14.9%], C⋯C [Fig. 4(e); 11.9%] and O⋯H/H⋯O [Fig. 4(f); 9.8%] interactions contribute the most to the surface contacts. The crystal packing is additionally influenced by Br⋯C/C⋯Br (2.0%), Br⋯Br (0.8%), N⋯N (2.6%) and O⋯C/C⋯O (0.2%) contacts. The Hirshfeld surface study confirms the significance of H-atom interactions in the packing formation. The large number of H⋯H, C⋯H/H⋯C, Br⋯H/H⋯Br, C⋯C and O⋯H/H⋯O interactions indicates that van der Waals interactions and hydrogen bonding are important in the crystal packing (Hathwar et al., 2015 ).

Figure 4
The two-dimensional fingerprint plots of the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) C⋯H/H⋯C, (d) Br⋯H/H⋯Br, (e) C⋯C and (f) O⋯H/H⋯O interactions. d_e and d_i represent the distances from a point on the Hirshfeld surface to the nearest atoms outside (external) and inside (internal) the surface.

4. Database survey

Four related compounds were found as a result of a search for the `(2E)-1,3-diphenylprop-2-en-1-one' unit in the Cambridge Structural Database (CSD, Version 5.42, update of September 2021; Groom et al., 2016 ), viz. CSD refcodes KOCZUA (Bindya et al., 2019 ), RUCKIM (Spruce et al., 2020 ), XOLLOC (Çelikesir et al., 2019 ) and OBIYUW01 (Atioğlu et al., 2019 ).

In the crystal of KOCZUA, the shortest intermolecular contacts are Cl⋯O [3.173 (3) Å]; these link the molecules to form a 2₁ helix propagating along the b-axis direction. The helices are linked by offset π–π interactions [intercentroid distance = 3.983 (1) Å], forming layers lying parallel to the ab plane. In the crystal of RUCKIM, the molecules are linked through type II halogen bonds, forming a sheet structure parallel to the bc plane. Weak intermolecular C—H⋯π interactions are observed between the sheets. In the crystal of XOLLOC, molecules are linked via pairs of C—H⋯O interactions with an R₂²(14) ring motif, forming inversion dimers. The dimers are linked into a tape structure running along [101] via C—H⋯π interactions. In the crystal of OBIYUW01, molecules are linked by C—H⋯π interactions between the bromophenyl and fluorophenyl rings, resulting in a two-dimensional layered structure parallel to the ab plane. The molecular packing is consolidated by weak Br⋯H and F⋯H contacts.

5. Synthesis and crystallization

The title compound was synthesized using a reported procedure (Chithiraikumar et al., 2021 ) and colourless crystals were obtained upon recrystallization from an ethanol/water (3:1 v/v) solution at room temperature.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All H atoms were placed in their geometrically calculated positions and refined using a riding model, with C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C) for aromatic H atoms, and C—H = 0.98 Å and U_iso(H) = 1.5U_eq(C) for methyl H atoms.

Table 3
Experimental details

Crystal data
Chemical formula	C₁₆H₁₃BrO
M_r	301.17
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	3.942, 11.5915 (2), 28.0387 (4)
V (Å³)	1281.19 (3)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	4.23
Crystal size (mm)	0.35 × 0.09 × 0.07

Data collection
Diffractometer	Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ )
T_min, T_max	0.251, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14537, 2657, 2627
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.632

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.052, 1.14
No. of reflections	2657
No. of parameters	165
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.42
Absolute structure	Refined as an inversion twin
Absolute structure parameter	0.53 (2)
Computer programs: CrysAlis PRO (Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ), SHELXT2018 (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2290092

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989023007387/tx2073sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023007387/tx2073Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2022); cell refinement: CrysAlis PRO (Rigaku OD, 2022); data reduction: CrysAlis PRO (Rigaku OD, 2022); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

(2E)-1-(4-Bromophenyl)-3-(2-methylphenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₃BrO	D_x = 1.561 Mg m⁻³
M_r = 301.17	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 12560 reflections
a = 3.942 Å	θ = 3.8–76.9°
b = 11.5915 (2) Å	µ = 4.23 mm⁻¹
c = 28.0387 (4) Å	T = 100 K
V = 1281.19 (3) Å³	Needle, colourless
Z = 4	0.35 × 0.09 × 0.07 mm
F(000) = 608

Data collection top

Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector	2627 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	R_int = 0.025
φ and ω scans	θ_max = 77.1°, θ_min = 3.2°
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2022)	h = −4→4
T_min = 0.251, T_max = 1.000	k = −14→14
14537 measured reflections	l = −35→34
2657 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.022	w = 1/[σ²(F_o²) + (0.0121P)² + 1.3924P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.052	(Δ/σ)_max = 0.001
S = 1.14	Δρ_max = 0.51 e Å⁻³
2657 reflections	Δρ_min = −0.42 e Å⁻³
165 parameters	Absolute structure: Refined as an inversion twin
0 restraints	Absolute structure parameter: 0.53 (2)

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.

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
C1	0.6338 (7)	0.6732 (2)	0.28488 (10)	0.0156 (6)
C2	0.5186 (8)	0.5849 (3)	0.31975 (11)	0.0179 (6)
H2	0.576288	0.506108	0.315259	0.021*
C3	0.3333 (8)	0.6169 (3)	0.35751 (10)	0.0167 (6)
H3	0.272264	0.696111	0.359037	0.020*
C4	0.2138 (8)	0.5441 (3)	0.39673 (9)	0.0162 (5)
C5	0.0419 (8)	0.5941 (3)	0.43586 (11)	0.0199 (6)
C6	−0.0614 (9)	0.5231 (3)	0.47322 (11)	0.0243 (7)
H6	−0.174643	0.556148	0.499821	0.029*
C7	−0.0025 (9)	0.4050 (3)	0.47241 (12)	0.0260 (8)
H7	−0.075592	0.358302	0.498276	0.031*
C8	0.1629 (10)	0.3552 (3)	0.43386 (11)	0.0244 (7)
H8	0.202810	0.274348	0.433117	0.029*
C9	0.2691 (8)	0.4245 (3)	0.39655 (10)	0.0200 (6)
H9	0.382068	0.390249	0.370170	0.024*
C10	−0.0317 (9)	0.7216 (3)	0.43748 (12)	0.0225 (7)
H10A	−0.155611	0.739898	0.466828	0.034*
H10B	−0.169550	0.743225	0.409802	0.034*
H10C	0.182210	0.764687	0.436880	0.034*
C11	0.7811 (8)	0.6341 (2)	0.23829 (10)	0.0151 (5)
C12	0.7419 (7)	0.5219 (2)	0.22102 (9)	0.0170 (6)
H12	0.629276	0.465770	0.239962	0.020*
C13	0.8664 (8)	0.4916 (2)	0.17629 (11)	0.0180 (6)
H13	0.839832	0.415359	0.164401	0.022*
C14	1.0295 (8)	0.5750 (3)	0.14959 (10)	0.0170 (6)
C15	1.0768 (8)	0.6869 (3)	0.16597 (11)	0.0178 (6)
H15	1.193503	0.742210	0.147111	0.021*
C16	0.9500 (8)	0.7159 (3)	0.21041 (11)	0.0172 (6)
H16	0.978056	0.792262	0.222085	0.021*
Br1	1.19480 (8)	0.53645 (3)	0.08770 (2)	0.02188 (9)
O1	0.6109 (6)	0.77583 (19)	0.29371 (8)	0.0242 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0136 (15)	0.0168 (14)	0.0164 (13)	0.0005 (11)	−0.0014 (11)	0.0006 (11)
C2	0.0207 (16)	0.0164 (14)	0.0165 (14)	0.0013 (12)	0.0014 (12)	−0.0001 (11)
C3	0.0164 (13)	0.0177 (13)	0.0160 (13)	0.0015 (13)	−0.0028 (12)	−0.0018 (11)
C4	0.0129 (13)	0.0224 (13)	0.0134 (11)	−0.0004 (13)	−0.0030 (9)	0.0003 (11)
C5	0.0137 (14)	0.0316 (18)	0.0145 (14)	−0.0011 (13)	−0.0031 (12)	−0.0034 (13)
C6	0.0193 (14)	0.040 (2)	0.0142 (13)	−0.0042 (16)	−0.0013 (11)	−0.0015 (14)
C7	0.0249 (18)	0.038 (2)	0.0153 (15)	−0.0111 (15)	−0.0042 (13)	0.0066 (14)
C8	0.0264 (17)	0.0242 (16)	0.0226 (15)	−0.0024 (15)	−0.0079 (15)	0.0043 (12)
C9	0.0205 (17)	0.0229 (14)	0.0166 (13)	0.0004 (12)	−0.0016 (11)	0.0005 (10)
C10	0.0194 (16)	0.0280 (17)	0.0203 (16)	0.0003 (14)	0.0009 (13)	−0.0072 (13)
C11	0.0128 (13)	0.0171 (13)	0.0155 (13)	0.0022 (11)	−0.0008 (11)	0.0023 (10)
C12	0.0162 (15)	0.0178 (14)	0.0170 (12)	−0.0007 (12)	0.0021 (10)	0.0043 (11)
C13	0.0200 (16)	0.0151 (14)	0.0190 (14)	0.0005 (11)	0.0005 (12)	−0.0003 (10)
C14	0.0133 (14)	0.0253 (16)	0.0123 (13)	0.0024 (11)	0.0009 (11)	−0.0012 (11)
C15	0.0160 (14)	0.0194 (15)	0.0181 (14)	−0.0021 (12)	−0.0007 (11)	0.0042 (11)
C16	0.0172 (14)	0.0151 (14)	0.0194 (14)	−0.0023 (12)	−0.0019 (12)	0.0009 (11)
Br1	0.02033 (14)	0.03011 (16)	0.01522 (13)	−0.00038 (13)	0.00375 (12)	−0.00153 (13)
O1	0.0303 (14)	0.0171 (11)	0.0252 (11)	0.0010 (9)	0.0064 (10)	−0.0025 (9)

Geometric parameters (Å, º) top

C1—O1	1.218 (4)	C8—H8	0.9500
C1—C2	1.487 (4)	C9—H9	0.9500
C1—C11	1.500 (4)	C10—H10A	0.9800
C2—C3	1.339 (4)	C10—H10B	0.9800
C2—H2	0.9500	C10—H10C	0.9800
C3—C4	1.464 (4)	C11—C12	1.396 (4)
C3—H3	0.9500	C11—C16	1.398 (4)
C4—C9	1.404 (4)	C12—C13	1.392 (4)
C4—C5	1.414 (4)	C12—H12	0.9500
C5—C6	1.393 (5)	C13—C14	1.381 (4)
C5—C10	1.507 (5)	C13—H13	0.9500
C6—C7	1.388 (5)	C14—C15	1.389 (4)
C6—H6	0.9500	C14—Br1	1.907 (3)
C7—C8	1.389 (5)	C15—C16	1.384 (4)
C7—H7	0.9500	C15—H15	0.9500
C8—C9	1.384 (4)	C16—H16	0.9500

O1—C1—C2	121.1 (3)	C4—C9—H9	119.2
O1—C1—C11	120.1 (3)	C5—C10—H10A	109.5
C2—C1—C11	118.9 (3)	C5—C10—H10B	109.5
C3—C2—C1	119.7 (3)	H10A—C10—H10B	109.5
C3—C2—H2	120.1	C5—C10—H10C	109.5
C1—C2—H2	120.1	H10A—C10—H10C	109.5
C2—C3—C4	127.6 (3)	H10B—C10—H10C	109.5
C2—C3—H3	116.2	C12—C11—C16	119.4 (3)
C4—C3—H3	116.2	C12—C11—C1	122.8 (3)
C9—C4—C5	118.8 (3)	C16—C11—C1	117.8 (3)
C9—C4—C3	121.1 (3)	C13—C12—C11	120.6 (3)
C5—C4—C3	120.1 (3)	C13—C12—H12	119.7
C6—C5—C4	118.8 (3)	C11—C12—H12	119.7
C6—C5—C10	120.0 (3)	C14—C13—C12	118.4 (3)
C4—C5—C10	121.2 (3)	C14—C13—H13	120.8
C7—C6—C5	121.4 (3)	C12—C13—H13	120.8
C7—C6—H6	119.3	C13—C14—C15	122.5 (3)
C5—C6—H6	119.3	C13—C14—Br1	119.2 (2)
C6—C7—C8	120.1 (3)	C15—C14—Br1	118.3 (2)
C6—C7—H7	119.9	C16—C15—C14	118.4 (3)
C8—C7—H7	119.9	C16—C15—H15	120.8
C9—C8—C7	119.3 (3)	C14—C15—H15	120.8
C9—C8—H8	120.4	C15—C16—C11	120.7 (3)
C7—C8—H8	120.4	C15—C16—H16	119.7
C8—C9—C4	121.6 (3)	C11—C16—H16	119.7
C8—C9—H9	119.2

O1—C1—C2—C3	12.0 (5)	C3—C4—C9—C8	178.7 (3)
C11—C1—C2—C3	−168.2 (3)	O1—C1—C11—C12	−164.3 (3)
C1—C2—C3—C4	−176.3 (3)	C2—C1—C11—C12	15.9 (4)
C2—C3—C4—C9	−4.4 (5)	O1—C1—C11—C16	12.6 (4)
C2—C3—C4—C5	175.1 (3)	C2—C1—C11—C16	−167.2 (3)
C9—C4—C5—C6	1.1 (5)	C16—C11—C12—C13	−0.6 (4)
C3—C4—C5—C6	−178.4 (3)	C1—C11—C12—C13	176.2 (3)
C9—C4—C5—C10	−178.6 (3)	C11—C12—C13—C14	0.1 (4)
C3—C4—C5—C10	1.9 (5)	C12—C13—C14—C15	0.8 (5)
C4—C5—C6—C7	−0.8 (5)	C12—C13—C14—Br1	−178.8 (2)
C10—C5—C6—C7	178.9 (3)	C13—C14—C15—C16	−1.1 (5)
C5—C6—C7—C8	0.1 (6)	Br1—C14—C15—C16	178.5 (2)
C6—C7—C8—C9	0.3 (5)	C14—C15—C16—C11	0.6 (5)
C7—C8—C9—C4	0.1 (5)	C12—C11—C16—C15	0.3 (5)
C5—C4—C9—C8	−0.7 (5)	C1—C11—C16—C15	−176.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	0.95	2.45	2.791 (4)	101
C12—H12···O1ⁱ	0.95	2.58	3.200 (3)	124

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Summary of short interatomic contacts (Å) in the title compound top

C3···H10B	2.85	x+1, y, z
Br1···H7	3.17	-x+3/2, -y+1, z-1/2
O1···H12	2.58	-x+1, y+1/2, -z+1/2
H15···H9	2.45	-x+2, y+1/2, -z+1/2
C10···H10A	3.10	x+1/2, -y+3/2, -z+1

Acknowledgements

This paper was supported by Baku State University and the RUDN University Strategic Academic Leadership Program. Authors contributions are as follows: conceptualization by ANK and IGM; methodology by ANK, FNN and IGM; investigation by ANK, MA and FNN; writing (original draft) by MA and ANK; writing (review and editing of the manuscript) by MA and ANK; visualization by MA, ANK and IGM; funding acquisition by VNK, AB and ANK; resources by AB, VNK and KAA; supervision by ANK and MA.

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