Synthesis and structure of 2-oxo-2H-chromen-4-yl 4-bromo­benzoate: work carried out as part of the CNRS AFRAMED project

Bationo, V.; Kambo, K.R.; Sorgho, B.; Sombié, C.B.; Thiam, E.W.; Semdé, R.; Djandé, A.; Lecomte, C.; Wenger, E.

doi:10.1107/S2056989025000246

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ISSN: 2056-9890

Volume 81| Part 3| March 2025|

https://doi.org/10.1107/S2056989025000246

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Synthesis and structure of 2-oxo-2H-chromen-4-yl 4-bromobenzoate: work carried out as part of the CNRS AFRAMED project

Valentin Bationo,^a Konan René Kambo,^b Brahima Sorgho,^a Charles Bavouma Sombié,^c El Walda Thiam,^d Rasmané Semdé,^c Abdoulaye Djandé,^a Claude Lecomte ^e and Emmanuel Wenger ^e ^*

^aLaboratory of Molecular Chemistry and Materials (LC2M), University Joseph KI-ZERBO, 03 BP 7021 Ouagadougou 03, Burkina Faso, ^bLaboratory of Environmental Science and Technology, University Jean Lorougnon GUEDE of Daloa, BP 150 Daloa, Côte d'Ivoire, ^cLaboratory of Drug Development, Center of Training, Research and Expertise in Pharmaceutical Sciences (CFOREM), University Joseph KI-ZERBO, 03 BP 7021, Ouagadougou 03, Burkina Faso, ^dLaboratory of Environment, Health and Society, University of Nouakchott, BP 880-Nouakchott, Mauritania, and ^eCRM2, CNRS-Université de Lorraine, Vandoeuvre-lès-Nancy CEDEX BP 70239, France
^*Correspondence e-mail: emmanuel.wenger@univ-lorraine.fr;_sorghobrahima3@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 3 December 2024; accepted 10 January 2025; online 7 February 2025)

In the title compound, C₁₆H₉BrO₄, the dihedral angle between the chromen-2-one ring system (r.m.s. deviation = 0.006 Å) and the bromobenzene ring is 10.29 (6)°. In the crystal, the molecules are connected through C—H⋯O hydrogen bonds and π–π stacking interactions. According to a Hirshfeld surface analysis, H⋯H (22.4%), O⋯H/H⋯O (23.6%) and C⋯H/H⋯C (21%) interactions are the most significant contributors to the crystal packing.

Keywords: crystal structure; hydrogen bonds; Hirshfeld surface analysis; coumarin.

CCDC reference: 2416578

1. AFRAMED and chemical context

This work was carried out as part of the CNRS AFRAMED project, which aims to train African Partners (young lecturers with permanent positions) in X-ray diffraction and provide regional laboratories, which serve as focal points to assist their colleagues for remote measurements (Abdel-Aal et al., 2023 ). Coumarin derivatives remain one of our research priorities due to their versatile range of activities, such as anticoagulant, anti-inflammatory, antiviral, antimicrobial, anticancer, antioxidant (Todorov et al., 2023 ), anti-glaucoma (Ziki et al., 2023 ) and anti-Parkisonian effects (Kambo et al., 2024 ). Here we report one result of this training: the synthesis, crystal structure and Hirshfeld surface analysis of the title coumarin derivative, C₁₆H₉BrO₄ (I).

2. Structural commentary

Compound (I) crystallizes in the orthorhombic space group P2₁2₁2₁ with one molecule in the asymmetric unit (Fig. 1). The side chain is titled with respect to the chromen-2-one ring system with torsion angles C9—C8—O2—C7 = −12.3 (4)° and C16—C8—O2—C7 = 169.9 (2)°. As expected, the chromen-2-one ring (C8—H16) system is almost planar, with a maximum deviation from the mean plane of 0.030 (2) Å for atom O3. The dihedral angle between this coumarin ring and the C1–C6 phenyl group in the 4-bromobenzoate moiety is 10.29 (6)°. An inspection of the bond lengths shows that there is a slight asymmetry of the electronic distribution around the pyrone ring, as shown by the differences between C8—C9 [1.350 (3) Å] and C9—C10 [1.452 (4) Å]. This suggests that the electron density is preferentially located in the formal C8=C9 double bond of the pyrone ring, as seen in other coumarin derivatives (Gomes et al., 2016 ; Ouédraogo et al., 2018 ). One intramolecular short contact exists between the C9—H9 methine group and atom O1 (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1	1.00 (4)	2.26 (4)	2.788 (3)	111 (3)
C15—H15⋯O3ⁱ	0.97 (3)	2.36 (4)	3.079 (3)	131 (3)
Symmetry code: (i) .

Figure 1
The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.

3. Supramolecular features and Hirshfeld surface analysis

In the crystal of (I), a weak C15—H15⋯O3 hydrogen bond links the molecules into [1 $[\overline{1}]$ 0] chains (Table 1, Fig. 2). The three-dimensional architecture is further consolidated by aromatic π-stacking interactions: the Cg1⋯Cg3(1 + x, y, z) separation is 3.8770 (19) Å, where Cg1 and Cg3 are the centroids of the C8–C10/O4/C11/C16 and C11–C16 rings, respectively.

Figure 2
The unit-cell packing of (I) showing a hydrogen-bonded [1 $[\overline{1}]$ 0] chain: dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen-bonding interactions have been omitted for clarity.

The intermolecular interactions in (I) were further quantified by Hirshfeld surface analysis (Fig. 3) using CrystalExplorer (Spackman et al., 2023 ). The interactions mentioned above are confirmed by the two-dimensional fingerprint plots for (I) (Fig. 4). The greatest contributions are from O⋯H/H⋯O (23.6%), H⋯H (22.4%) and C⋯H/H⋯C (21%) while the Br⋯H/H⋯Br and Br⋯C/C⋯Br contacts contribute 9.6 and 6.4%, respectively.

Figure 3
The Hirshfeld surface of (I) mapped over d_norm. Dotted lines (magenta) represent hydrogen bonds.

Figure 4
Fingerprint plots of (I): (a) H⋯H, (b) O⋯H, (c) C⋯O, (d) C⋯H, (e) Br⋯O, (f) Br⋯H and (g) Br⋯C: d_i is the closest internal distance from a given point on the Hirshfeld surface and d_e is the closest external contact.

4. Database survey

A search of the Cambridge Structural Database (CSD, version 5.43; update 3, September 2022; Groom et al., 2016 ) for structures having a coumarin motif similar to (I) returned thirteen hits, including (7-chloro-2-oxo-2H-chromen-4-yl)methyldimethylcarbamodithioate (CSD refcode XUFGOW; Kavitha et al., 2015 ); (6-bromo-2-oxo-2H-chromen-4-yl)methyl diethylcarbamodithioate (NUZJOJ; Vinduvahini et al., 2016 ); (5,7-dimethyl-2-oxo-2H-chromen-4-yl)methyl morpholine-4-carbodithioate (UDOGIF01; Anitha et al., 2016 ); (7-fluoro-2-oxo-2H-chromen-4-yl)methyl morpholine-4-carbodithioate (UYVEE; Anitha et al., 2015 ); (7,8-dimethyl-2-oxo-2H-chromen-4-yl)methyl piperidine-1-carbodithioate (NAGWAW; Ravi et al., 2016 ); methyl 2-[(2-oxo-2H-1-benzopyran-4-yl)amino]benzoate (DIWPAE; Hollauer et al., 2023 ). In 2-oxo-2H-chromen-4-yl 4-(dimetylamino)benzoate (AYOXAO; Abou et al., 2011 ), the benzoate ring is oriented at a dihedral angle of 43.43 (6)° with the chromene ring system while in 2-oxo-2H-chromen-4-yl 4-tert-butylbenzoate (GARHAK; Abou et et al., 2012b ), the benzene ring of the benzoate group is oriented at a dihedral angle of 60.70 (7)° with the chromene ring system. In 2-oxo-2H-chromen-4-yl 4-methoxybenzoate (PECVUQ; Abou et al., 2012a ), the chromen-2-one ring and the 4-methoxybenzoate side chain are inclined to one another at a dihedral angle of 69.82 (9)° and in 2-oxo-2H-chromen-4-yl 4-methylbenzoate (AFOQET; Abou et al., 2013 ), the chromene-2-one ring and the 4-methylbenzoate side chain are inclined to one another at a dihedral angle of 64.79 (10)° in one molecule and 88.3 (1)° in the other. In 2-oxo-2H-chromen-4-yl propionate (AGAREH; Bibila Mayaya Bisseyou et al., 2013 ), the 2-oxo-2H-chromene ring system and the non-H atom of the 4-substituent all lie on a crystallographic mirror plane. In 2-oxo-2H-1-benzopyran-4-yl 3,3-dimethylbutanoate (JOMHUS; Bationo et al., 2024a ), the 2-oxo-2H-1-benzopyran-4-yl 3,3-dimethylbutanoate the coumarin ring system is oriented at a dihedral angle of 56.24 (18)° with the butanoate moiety. In 2-oxo-2H-chromen-4-yl pentanoate (PONXUP; Bationo et al., 2024b ), the dihedral angle between the coumarin ring system and the pentanoate is 36.26 (8)°.

5. Synthesis and crystallization

To a solution of 4-bromobenzoyl chloride (6.2 mmol, 1.35 g) in dried tetrahydrofurn (30 ml) were added dried triethylamine (3 molar equivalents, 2.6 ml) and 4-hydroxycoumarin (6.17 mmol, 1.00 g) in small portions over 30 min. The mixture was then refluxed for 4 h and poured into 40 ml of chloroform. The solution was acidified with dilute (5%) hydrochloric acid until its discoloration was complete. The organic layers were extracted, concentrated under vacuum until a slight cloudiness was obtained and left in an ice bath. The resulting crude product was filtered off with suction, washed with petroleum ether and purified by recrystallization from a chloroform–hexane solvent mixture: yield 71%.

Colorless crystals of (I) suitable for data collection were obtained by recrystallization from acetone solution. The melting point was measured in an open capillary with a Cole–Parmer STUART MP. 800D Series-Melting S apparatus and is thus uncorrected, m.p. 423–425 K.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Hydrogen atoms were located in difference-Fourier maps and their positions and U_iso values were freely refined.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₉BrO₄
M_r	345.14
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	5.4003 (11), 6.367 (2), 38.404 (8)
V (Å³)	1320.4 (6)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	3.13
Crystal size (mm)	0.27 × 0.21 × 0.13

Data collection
Diffractometer	Bruker D8 Venture
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.731, 0.895
No. of measured, independent and observed [I > 2σ(I)] reflections	37156, 4975, 4880
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.768

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.064, 1.11
No. of reflections	4975
No. of parameters	226
No. of restraints	2
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.89, −0.87
Absolute structure	Flack x determined using 1967 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.008 (3)
Computer programs: APEX2 and SAINT (Bruker, 2014 ), SHELXT (Sheldrick, 2015a ), SHELXL2013 (Sheldrick, 2015b ).

Supporting information

CCDC reference: 2416578

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989025000246/hb8116sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025000246/hb8116Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025000246/hb8116Isup3.cml

checkCIF report

Computing details top

2-Oxo-2H-chromen-4-yl 4-bromobenzoate top

Crystal data top

C₁₆H₉BrO₄	D_x = 1.736 Mg m⁻³
M_r = 345.14	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 4940 reflections
a = 5.4003 (11) Å	θ = 2.3–30.6°
b = 6.367 (2) Å	µ = 3.13 mm⁻¹
c = 38.404 (8) Å	T = 100 K
V = 1320.4 (6) Å³	Prism, colourless
Z = 4	0.27 × 0.21 × 0.13 mm
F(000) = 688

Data collection top

Bruker D8 Venture diffractometer	4880 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.034
Absorption correction: multi-scan (SADBAS; Krause et al., 2015)	θ_max = 33.1°, θ_min = 3.2°
T_min = 0.731, T_max = 0.895	h = −7→8
37156 measured reflections	k = −9→9
4975 independent reflections	l = −58→58

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.029	w = 1/[σ²(F_o²) + (0.0042P)² + 1.5505P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.064	(Δ/σ)_max = 0.001
S = 1.11	Δρ_max = 0.89 e Å⁻³
4975 reflections	Δρ_min = −0.87 e Å⁻³
226 parameters	Absolute structure: Flack x determined using 1967 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
2 restraints	Absolute structure parameter: 0.008 (3)

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	0.42360 (5)	−0.17161 (4)	0.27424 (2)	0.02298 (6)
C5	0.3903 (4)	0.3282 (4)	0.34326 (6)	0.0189 (4)
O2	0.2448 (3)	0.6887 (3)	0.37643 (4)	0.0196 (3)
C2	0.0989 (5)	0.1701 (5)	0.28876 (6)	0.0209 (4)
O3	−0.1051 (4)	1.3465 (3)	0.41125 (5)	0.0301 (4)
C8	0.2098 (5)	0.8636 (4)	0.39677 (6)	0.0173 (4)
O4	0.2035 (4)	1.2090 (3)	0.44169 (5)	0.0231 (4)
O1	−0.1096 (4)	0.7132 (3)	0.34419 (6)	0.0291 (5)
C7	0.0804 (6)	0.6245 (4)	0.35106 (6)	0.0189 (4)
C3	0.0272 (4)	0.3517 (4)	0.30635 (6)	0.0192 (4)
C6	0.4630 (5)	0.1452 (4)	0.32592 (6)	0.0188 (4)
C15	0.5666 (5)	0.7219 (4)	0.43182 (6)	0.0190 (4)
C4	0.1718 (5)	0.4307 (4)	0.33372 (6)	0.0175 (4)
C9	0.0415 (5)	1.0175 (4)	0.39187 (7)	0.0209 (5)
C12	0.5369 (5)	1.0775 (4)	0.47484 (7)	0.0225 (5)
C11	0.3749 (5)	1.0522 (4)	0.44687 (6)	0.0183 (4)
C10	0.0358 (5)	1.1996 (4)	0.41461 (7)	0.0219 (5)
C16	0.3865 (5)	0.8749 (4)	0.42525 (6)	0.0162 (4)
C14	0.7299 (5)	0.7462 (4)	0.45953 (7)	0.0217 (5)
C1	0.3163 (5)	0.0707 (4)	0.29888 (6)	0.0179 (4)
C13	0.7138 (5)	0.9227 (5)	0.48089 (7)	0.0228 (5)
H15	0.579 (7)	0.600 (5)	0.4167 (8)	0.019 (8)*
H9	−0.096 (8)	1.018 (6)	0.3743 (9)	0.029 (9)*
H2	−0.004 (4)	0.106 (4)	0.2698 (6)	0.026 (9)*
H13	0.823 (6)	0.936 (5)	0.5001 (9)	0.021 (9)*
H3	−0.124 (6)	0.423 (5)	0.2999 (8)	0.015 (8)*
H12	0.518 (6)	1.206 (6)	0.4896 (9)	0.027 (9)*
H6	0.597 (7)	0.074 (5)	0.3328 (8)	0.016 (8)*
H14	0.851 (7)	0.640 (6)	0.4629 (9)	0.026 (9)*
H5	0.492 (7)	0.386 (6)	0.3636 (10)	0.037 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02724 (11)	0.02177 (10)	0.01994 (10)	0.00231 (11)	−0.00180 (10)	−0.00603 (9)
C5	0.0192 (10)	0.0202 (10)	0.0172 (9)	−0.0005 (10)	−0.0020 (8)	−0.0020 (9)
O2	0.0223 (8)	0.0163 (8)	0.0201 (8)	0.0048 (7)	−0.0044 (6)	−0.0035 (7)
C2	0.0224 (11)	0.0223 (10)	0.0181 (9)	0.0002 (12)	−0.0044 (8)	0.0000 (9)
O3	0.0362 (11)	0.0234 (9)	0.0308 (9)	0.0166 (10)	0.0030 (8)	−0.0011 (8)
C8	0.0202 (10)	0.0147 (10)	0.0169 (9)	0.0023 (8)	0.0016 (8)	0.0000 (7)
O4	0.0279 (9)	0.0174 (9)	0.0238 (8)	0.0066 (7)	0.0018 (7)	−0.0035 (7)
O1	0.0261 (10)	0.0266 (10)	0.0345 (10)	0.0087 (8)	−0.0092 (8)	−0.0063 (8)
C7	0.0213 (10)	0.0174 (10)	0.0182 (9)	0.0006 (9)	−0.0019 (9)	0.0013 (7)
C3	0.0190 (10)	0.0192 (11)	0.0194 (9)	0.0003 (9)	−0.0020 (8)	0.0010 (8)
C6	0.0185 (11)	0.0193 (11)	0.0185 (9)	0.0014 (9)	−0.0014 (8)	−0.0014 (8)
C15	0.0213 (10)	0.0177 (10)	0.0180 (9)	0.0037 (9)	−0.0007 (9)	−0.0007 (7)
C4	0.0199 (10)	0.0177 (10)	0.0148 (9)	−0.0009 (9)	−0.0008 (8)	−0.0002 (8)
C9	0.0231 (12)	0.0187 (10)	0.0210 (10)	0.0073 (9)	0.0002 (9)	0.0000 (8)
C12	0.0266 (14)	0.0215 (11)	0.0195 (10)	−0.0011 (10)	0.0015 (9)	−0.0045 (9)
C11	0.0207 (12)	0.0162 (10)	0.0181 (10)	0.0020 (8)	0.0019 (8)	−0.0005 (8)
C10	0.0248 (12)	0.0177 (11)	0.0231 (10)	0.0057 (9)	0.0043 (9)	0.0003 (8)
C16	0.0190 (11)	0.0144 (9)	0.0150 (9)	0.0017 (8)	0.0021 (8)	−0.0002 (7)
C14	0.0228 (11)	0.0225 (11)	0.0199 (11)	0.0037 (10)	−0.0014 (9)	0.0002 (9)
C1	0.0216 (11)	0.0178 (10)	0.0141 (9)	−0.0010 (9)	0.0029 (8)	−0.0009 (8)
C13	0.0242 (12)	0.0247 (12)	0.0195 (11)	−0.0020 (10)	−0.0020 (9)	−0.0015 (9)

Geometric parameters (Å, º) top

Br1—C1	1.900 (3)	C3—C4	1.403 (3)
C5—C4	1.397 (4)	C3—H3	0.97 (3)
C5—C6	1.398 (4)	C6—C1	1.389 (3)
C5—H5	1.02 (4)	C6—H6	0.89 (4)
O2—C8	1.373 (3)	C15—C14	1.391 (4)
O2—C7	1.380 (3)	C15—C16	1.400 (3)
C2—C1	1.389 (4)	C15—H15	0.97 (3)
C2—C3	1.394 (4)	C9—C10	1.452 (4)
C2—H2	1.002 (12)	C9—H9	1.00 (4)
O3—C10	1.213 (3)	C12—C13	1.392 (4)
C8—C9	1.350 (3)	C12—C11	1.394 (4)
C8—C16	1.453 (3)	C12—H12	1.00 (4)
O4—C11	1.376 (3)	C11—C16	1.403 (3)
O4—C10	1.380 (3)	C14—C13	1.394 (4)
O1—C7	1.200 (3)	C14—H14	0.95 (4)
C7—C4	1.487 (3)	C13—H13	0.95 (3)

C4—C5—C6	120.1 (2)	C3—C4—C7	116.6 (2)
C4—C5—H5	119 (2)	C8—C9—C10	120.7 (2)
C6—C5—H5	121 (2)	C8—C9—H9	127 (2)
C8—O2—C7	123.6 (2)	C10—C9—H9	113 (2)
C1—C2—C3	118.5 (2)	C13—C12—C11	118.5 (2)
C1—C2—H2	119.2 (9)	C13—C12—H12	124 (2)
C3—C2—H2	122.3 (9)	C11—C12—H12	118 (2)
C9—C8—O2	127.0 (2)	O4—C11—C12	116.7 (2)
C9—C8—C16	120.7 (2)	O4—C11—C16	121.9 (2)
O2—C8—C16	112.2 (2)	C12—C11—C16	121.4 (2)
C11—O4—C10	121.3 (2)	O3—C10—O4	117.3 (2)
O1—C7—O2	124.5 (2)	O3—C10—C9	124.4 (3)
O1—C7—C4	125.2 (2)	O4—C10—C9	118.3 (2)
O2—C7—C4	110.4 (2)	C15—C16—C11	119.0 (2)
C2—C3—C4	120.4 (2)	C15—C16—C8	123.9 (2)
C2—C3—H3	120.1 (19)	C11—C16—C8	117.2 (2)
C4—C3—H3	119.5 (19)	C15—C14—C13	120.0 (3)
C1—C6—C5	118.7 (2)	C15—C14—H14	118 (2)
C1—C6—H6	120 (2)	C13—C14—H14	122 (2)
C5—C6—H6	121 (2)	C2—C1—C6	122.4 (2)
C14—C15—C16	120.1 (2)	C2—C1—Br1	119.22 (19)
C14—C15—H15	120 (2)	C6—C1—Br1	118.39 (19)
C16—C15—H15	120 (2)	C12—C13—C14	121.0 (3)
C5—C4—C3	119.9 (2)	C12—C13—H13	120 (2)
C5—C4—C7	123.4 (2)	C14—C13—H13	119 (2)

C7—O2—C8—C9	−12.3 (4)	C11—O4—C10—C9	1.0 (4)
C7—O2—C8—C16	169.9 (2)	C8—C9—C10—O3	177.9 (3)
C8—O2—C7—O1	−0.3 (4)	C8—C9—C10—O4	−1.3 (4)
C8—O2—C7—C4	179.9 (2)	C14—C15—C16—C11	0.3 (4)
C1—C2—C3—C4	−0.3 (4)	C14—C15—C16—C8	179.5 (2)
C4—C5—C6—C1	1.1 (4)	O4—C11—C16—C15	179.5 (2)
C6—C5—C4—C3	−1.0 (4)	C12—C11—C16—C15	−0.7 (4)
C6—C5—C4—C7	179.4 (2)	O4—C11—C16—C8	0.3 (3)
C2—C3—C4—C5	0.6 (4)	C12—C11—C16—C8	−179.9 (2)
C2—C3—C4—C7	−179.8 (2)	C9—C8—C16—C15	−179.7 (2)
O1—C7—C4—C5	−177.8 (3)	O2—C8—C16—C15	−1.8 (3)
O2—C7—C4—C5	2.0 (3)	C9—C8—C16—C11	−0.6 (4)
O1—C7—C4—C3	2.5 (4)	O2—C8—C16—C11	177.3 (2)
O2—C7—C4—C3	−177.7 (2)	C16—C15—C14—C13	0.2 (4)
O2—C8—C9—C10	−176.5 (2)	C3—C2—C1—C6	0.4 (4)
C16—C8—C9—C10	1.0 (4)	C3—C2—C1—Br1	−177.87 (19)
C10—O4—C11—C12	179.6 (2)	C5—C6—C1—C2	−0.8 (4)
C10—O4—C11—C16	−0.6 (4)	C5—C6—C1—Br1	177.48 (19)
C13—C12—C11—O4	−179.7 (2)	C11—C12—C13—C14	0.1 (4)
C13—C12—C11—C16	0.5 (4)	C15—C14—C13—C12	−0.5 (4)
C11—O4—C10—O3	−178.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1	1.00 (4)	2.26 (4)	2.788 (3)	111 (3)
C15—H15···O3ⁱ	0.97 (3)	2.36 (4)	3.079 (3)	131 (3)

Symmetry code: (i) x+1, y−1, z.

Acknowledgements

The authors thank UNESCO, CNRS and the IUCr for their support to AFRAMED project. The authors also thank the CCDC for providing access to the Cambridge Structural Database through the FAIRE program.

Funding information

Funding for this research was provided by: CNRS through AFRAMED project and IUCr through Africa Initiative.

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