Crystal structure and Hirshfeld surface analysis of 2-benzyl-4,5-di­bromo-2,3,3a,4,5,6,7,7a-octa­hydro-3a,6-ep­oxy-1H-isoindol-1-one

Mertsalov, D.F.; Zaytsev, V.P.; Pokazeev, K.M.; Grigoriev, M.S.; Bachinsky, A.V.; Çelikesir, S.T.; Akkurt, M.; Mlowe, S.

doi:10.1107/S2056989021001481

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ISSN: 2056-9890

Volume 77| Part 3| March 2021| Pages 255-259

https://doi.org/10.1107/S2056989021001481

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Crystal structure and Hirshfeld surface analysis of 2-benzyl-4,5-dibromo-2,3,3a,4,5,6,7,7a-octahydro-3a,6-epoxy-1H-isoindol-1-one

Dmitriy F. Mertsalov,^a Vladimir P. Zaytsev,^a Kuzma M. Pokazeev,^a Mikhail S. Grigoriev,^b Alexander V. Bachinsky,^a Sevim Türktekin Çelikesir,^c Mehmet Akkurt ^c and Sixberth Mlowe ^d ^*

^aDepartment of Organic Chemistry, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., 117198, Moscow, Russian Federation, ^bFrumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky pr. 31, bld. 4, Moscow, 119071, Russian Federation, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^dUniversity of Dar es Salaam, Dar es Salaam University College of Education, Department of Chemistry, PO Box 2329, Dar es Salaam, Tanzania
^*Correspondence e-mail: sixberth.mlowe@duce.ac.tz

Edited by J. Reibenspies, Texas A & M University, USA (Received 25 January 2021; accepted 8 February 2021; online 12 February 2021)

The title compound, C₁₅H₁₅Br₂NO₂, crystallizes with two molecules in the asymmetric unit of the unit cell. In both molecules, the tetrahydrofuran rings adopt an envelope conformation with the O atom as the flap and the pyrrolidine rings adopt an envelope conformation. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming sheets lying parallel to the (002) plane. These sheets are connected only by weak van der Waals interactions. The most important contributions to the surface contacts are from H⋯H (44.6%), Br⋯H/H⋯Br (24.1%), O⋯H/H⋯O (13.5%) and C⋯H/H⋯C (11.2%) interactions, as concluded from a Hirshfeld surface analysis.

Keywords: crystal structure; pyrrolidine ring; tetrahydrofuran ring; epoxyisoindole moiety; Hirshfeld surface analysis.

CCDC reference: 2061968

1. Chemical context

Halogenation is a chemical reaction that involves the introduction of one or more halogen atoms to an organic molecule. The pathway and stereochemistry of halogenation reactions is dependent on the configuration of the starting olefine and the halogenating agent. The role/behavior of the attached halogen atom in olefines can be classified into the following types: (1) as an electron-withdrawing substituent, (2) as a halogen-bond donor center, and (3) as a non-covalent bond acceptor site. Thus, not only hydrogen bonding (Gurbanov et al., 2018 ; Kopylovich et al., 2011 ) or other types of non-covalent interactions (Afkhami et al., 2017 ; Asadov et al., 2016 ; Ma et al., 2017a ,b ; 2020 ; Mahmudov et al., 2010 ; 2019 ; 2020 , but also halogen bonding can be used in the design of olefines. In this work, we proposed and tested inexpensive and readily available bis[N,N-dimethylacetamide] hydrogen dibromobromate [(Me₂NCOMe)₂H]Br₃ as a bromine initiator and a source of a positively charged bromine ion (Rodygin et al., 1992 ; Prokop'eva et al., 1994 ; Prokop'eva, 2008 ). The choice of [(Me₂NCOMe)₂H]Br₃, obtained by one-pot synthesis from N,N-dimethylacetamide, hydrobromic acid and bromine, is down to the simplicity of the synthesis and isolation, and the unambiguous direction of the bromination process. In addition, [(Me₂NCOMe)₂H]Br₃ is an excellent reagent for functionalization of phenols and anilines (Rodygin et al., 1992; Mikhailov et al., 1993 ), and is also used in the synthesis of mono-bromo-substituted ketones (Rodygin et al., 1994 ; Burakov et al., 2001 ) and for the bromination of various alkenes and alkynes (Rodygin et al., 1994; Zaytsev et al., 2017 ). The present work is aimed at accumulating experimental data and establishing the rules of the halogenation in bridged epoxy-isoindolones (Zubkov et al., 2018 ; Zaytsev et al., 2020 ). The reaction of N-benzyltetrahydroepoxyisoindolone (1) with [(Me₂NCOMe)₂H]Br₃ in dry chloroform under reflux leads to the corresponding 2-benzyl-4,5-dibromohexahydro-3a,6-epoxyisoindol-1(4H)-one (2) (Fig. 1).

Figure 1
Synthesis scheme for 2-benzyl-4,5-dibromohexahydro-3a,6-epoxyisoindol-1(4H)-one (2)

2. Structural commentary

The asymmetric unit of the title compound (Fig. 2) contains two molecules of similar shape, hereafter referred to as molecules A (including atom C1A) and B (including atom C1B). The conformational differences between molecules A and B are highlighted in an overlay diagram shown in Fig. 3. The r.m.s. deviation of the overlay between the molecules A and B is 0.114 Å.

Figure 2
The two molecules (A and B) in the asymmetric unit of the title compound with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level.

Figure 3
Overlay image (OLEX2; Dolomanov et al., 2009

) of the two molecules (A and B) in the asymmetric unit of the title compound.

In both molecules A and B, the pyrrolidine rings (N1A/C5A–C8A and N1B/C5B–C8B), tetrahydrofuran rings (O1A/C1A–C3A/C6A, O1A/C3A–C6A and O1B/C1B–C3B/C6B, O1B/C3B–C6B) and six-membered rings (C1A–C6A and C1B–C6B), which generate epoxyisoindole moieties (O1A/N1A/C1A–C8A and O1B/N1B/C1B–C8B), are puckered. In molecule A, both tetrahydrofuran rings adopt an envelope conformation with puckering parameters (Cremer & Pople, 1975 ) Q(2) = 0.575 (3) Å, φ(2) = 182.2 (4)° for (O1A/C1A–C3A/C6A) and Q(2) = 0.558 (4) Å, φ(2) = 3.8 (4)° for (O1A/C3A–C6A), respectively. In molecule B, both tetrahydrofuran rings also adopt an envelope conformation with puckering parameters Q(2) = 0.575 (4) Å, φ(2) = 182.7 (4)° for (O1B/C1B–C3B/C6B) and Q(2) = 0.556 (4) Å, φ(2) = 3.7 (4)° for (O1B/C3B–C6B).

The five-membered pyrrolidine rings also exhibit an envelope conformation, with a maximum deviation from the mean plane of 0.155 (3) Å at C6A [puckering parameters Q(2) = 0.248 (4) Å, φ(2) = 77.7 (8)°] for molecule A and 0.153 (3) Å at C6B [puckering parameters Q(2) = 0.243 (4) Å, φ(2) = 75.0 (9)°] for molecule B. In both molecules, the six-membered ring has a boat conformation [Q_T = 0.921 (4) Å, θ = 91.8 (2)°, φ = 119.3 (2)° for molecule A; Q_T = 0.919 (4) Å, θ = 91.9 (2)°, φ = 119.6 (3)° for molecule B].

3. Supramolecular features

In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming sheets lying parallel to the (002) plane (Table 1, Figs. 4 and 5). These sheets are connected only by weak van der Waals interactions.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1A—H1A⋯O2Aⁱ	0.98	2.51	3.175 (4)	125
C4A—H4AB⋯Br2A	0.97	2.81	3.287 (4)	111
C5A—H5A⋯O2Aⁱ	0.98	2.64	3.271 (4)	123
C7A—H7AB⋯O2Aⁱ	0.97	2.53	3.186 (4)	125
C1B—H1B⋯O2Bⁱⁱ	0.98	2.39	3.104 (4)	129
C2B—H2B⋯O1A	0.98	2.38	3.341 (4)	168
C4B—H4BB⋯Br2B	0.97	2.83	3.301 (4)	111
C5B—H5B⋯O2Bⁱⁱ	0.98	2.57	3.247 (5)	126
C7B—H7BB⋯O2Bⁱⁱ	0.97	2.64	3.270 (5)	123
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 4
A view along the a axis of the intermolecular C—H⋯O interactions in the title compound.

Figure 5
A view along the b axis of the intermolecular C—H⋯O interactions in the title compound.

4. Hirshfeld surface analysis

The intermolecular interactions (Table 2) were investigated quantitatively and visualized with Crystal Explorer 3.1 (Wolff et al., 2012 ; Spackman et al., 2009 ). The Hirshfeld surface plotted over d_norm in the range −0.0815 to 0.9926 a.u. is shown in Fig. 6. The red spots on the Hirshfeld surface represent C—H⋯O contacts. Fig. 7 shows the full two-dimensional fingerprint plot and those delineated into the major contacts: the H⋯H (44.6%) interactions are the major factor in the crystal packing with Br⋯H/H⋯Br (24.1%), O⋯H/H⋯O (13.5%) and C⋯H/H⋯C (11.2%) interactions representing the next highest contributions. The percentage contributions of other weak interactions are listed in Table 3.

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

Contact	Distance	Symmetry operation
H2A⋯Br1A	3.21	2 − x, 1 − y, 1 − z
Br1A⋯Br2B	3.8655	2 − x, 1 − y, 1 − z
Br2A⋯Br1B	3.8993	2 − x, −y, 1 − z
O1A⋯H2B	2.38	x, y, z
O2A⋯H1A	2.51	$[{3\over 2}]$ − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
O2A⋯H11B	2.78	1 − x, − y, 1 − z
H7AA⋯C13B	2.85	1 − x, 1 − y, 1 − z
H11A⋯H5B	2.55	− $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, − $[{1\over 2}]$ + z
H13B⋯Br1B	3.13	1 − x, −y, 1 − z
O2B⋯H1B	2.39	$[{3\over 2}]$ − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z
H13B⋯H3B	2.42	1 − x, 1 − y, 1 − z

Table 3
Percentage contributions of interatomic contacts to the Hirshfeld surface for the title compound

Contact	Percentage contribution
H⋯H	44.6
Br⋯H/H⋯Br	24.1
O⋯H/H⋯O	13.5
C⋯H/H⋯C	11.2
Br⋯Br	3.9
C⋯C	2.0
N⋯H/H⋯N	0.5
Br⋯C/C⋯Br	0.3

Figure 6
A view of the three-dimensional Hirshfeld surface for the title compound, plotted over d_norm in the range −0.0815 to 0.9926 a.u.

Figure 7
A view of the two-dimensional fingerprint plots for the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) Br⋯H/H⋯Br, (d) O⋯H/H⋯O and (e) C⋯H/H⋯C interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

5. Database survey

A search of the Cambridge Structural Database (CSD version 5.40, update of September 2019; Groom et al., 2016 ) for structures having the epoxyisoindole moiety gave six hits, which closely resemble the title compound, viz. (3aR,6S,7aR)-7a-chloro-2-[(4-nitrophenyl)sulfonyl]-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole (CSD refcode AGONUH; Temel et al., 2013 ), (3aR,6S,7aR)-7a-chloro-6-methyl-2-[(4-nitrophenyl)sulfonyl]-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole (TIJMIK; Demircan et al., 2013 ), 5-chloro-7-methyl-3-[(4-methylphenyl)sulfonyl]-10-oxa-3-azatricyclo[5.2.1.01,5]dec-8-ene (YAXCIL; Temel et al., 2012 ), (3aR,6S,7aR)-7a-bromo-2-[(4-methylphenyl)sulfonyl]-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole (UPAQEI; Koşar et al., 2011 ), (3aR,6S,7aR)-7a-bromo-2-methylsulfonyl-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole (ERIVIL; Temel et al., 2011 ) and tert-butyl 3a-chloroperhydro-2,6a-epoxyoxireno(e)isoindole-5-carboxylate (MIGTIG; Koşar et al., 2007 ).

In the crystal of AGONUH, the molecules are linked by C—H⋯O hydrogen bonds into zigzag chains running along the b-axis direction. In TIJMIK, two types of C—H⋯O hydrogen bonds generate R₂²(20) and R₄⁴(26) rings, with adjacent rings running parallel to ac plane. In addition C—H⋯O hydrogen bonds form a C(6) chain, linking the molecules in the b-axis direction. In YAXCIL and UPAQEI, molecules are also linked by C—H⋯O hydrogen bonds. In the crystal of ERIVIL, weak intermolecular C—H⋯O hydrogen bonds link the molecules into R₂²(8) and R₂²(14) rings along the b-axis direction. In MIGTIG, the molecules are linked only by weak van der Waals interactions.

6. Synthesis and crystallization

A solution of isoindolone 1 (4 mmol) and the brominating agent (4 mmol) in dry chloroform (15 mL) was heated under reflux for 18 h (TLC control, EtOAc–hexane, 1:1). The reaction mixture was poured into H₂O (50 mL) and extracted with CHCl₃ (3 × 20 mL). The combined organic fractions were dried over anhydrous Na₂SO₄, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (SiO₂, 15 × 1.8 cm, hexane/EtOAc, 10:1). Colourless hexagonal prisms. Yield 0.46 g (29%), m.p. > 428 K (decomposition).

IR (KBr), ν (cm⁻¹): 1693 (N—C=O), 627 (C—Br). ¹H NMR (CDCl₃, 600 MHz, 301 K): δ = 7.37–7.34 (m, 2H, H-Ph), 7.32–7.29 (m, 1H, H-Ph), 7.24–7.22 (m, 2H, H-Ph), 4.71 (t, 1H, H6, J = 5.0), 4.54 (d, 1H, CH₂Ph, J = 15.1) and 4.48 (d, 1H, CH₂Ph, J = 15.1), 4.46 (ddd, 1H, H5, J = 1.5, J = 2.5, J = 5.0), 4.17 (d, 1H, H4, J = 2.5), 3.50 (d, 1H, J = 12.1) and 3.47 (d, 1H, H3, J = 12.1), 2.81 (dd, 1H, H7A, J = 4.7, J = 9.3), 2.73 (dd, 1H, H7B, J = 9.3, J = 12.8), 2.25–2.21 (m, 1H, H7A). ¹³C NMR (CDCl₃, 150.9 MHz, 301 K): δ = 172.9, 135.5, 128.8 (2C), 127.9 (2C), 127.7, 90.0, 80.6, 55.1, 48.9, 48.4, 46.5, 33.8, 30.2. MS (APCI): m/z = 400 [M + H]⁺ (⁸¹Br), 402 [M + H]⁺ (⁸¹Br, ⁷⁹Br), 404 [M + H]⁺ (⁷⁹Br).

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 4. C-bound H atoms were positioned geometrically, with C—H = 0.93 Å (for aromatic H atoms), C—H = 0.98 Å (for methine H atoms), 0.97 Å (for methylene H atoms) and 0.96 Å (for methyl H atoms), and constrained to ride on their parent atoms, with U_iso(H) =1.2U_eq(C) or 1.5U_eq(C-methyl). Ten reflections (101), ( $[\overline{1}]$ 01), (111), (002), ( $[\overline{1}]$ 11), (110), (200), ( $[\overline{1}]$ 03), ( $[\overline{2}]$ 02) and ( $[\overline{1}]$ 12) were obscured by the beam stop and omitted during the final refinement cycle.

Table 4
Experimental details

Crystal data
Chemical formula	C₁₅H₁₅Br₂NO₂
M_r	401.10
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	17.4839 (5), 8.2993 (3), 21.5120 (7)
β (°)	106.115 (2)
V (Å³)	2998.83 (17)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	5.41
Crystal size (mm)	0.14 × 0.13 × 0.13

Data collection
Diffractometer	Bruker Kappa APEXII area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2008 )
T_min, T_max	0.224, 0.294
No. of measured, independent and observed [I > 2σ(I)] reflections	32806, 6995, 3997
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.091, 1.02
No. of reflections	6995
No. of parameters	362
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.83, −0.66
Computer programs: APEX2 (Bruker, 2013 ), SAINT (Bruker, 2013), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ), OLEX2 (Dolomanov et al., 2009 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2061968

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989021001481/jy2005sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989021001481/jy2005Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: PLATON (Spek, 2020).

2-Benzyl-4,5-dibromo-2,3,3a,4,5,6,7,7a-octahydro-3a,6-epoxy-1H-isoindol-1-one top

Crystal data top

C₁₅H₁₅Br₂NO₂	F(000) = 1584
M_r = 401.10	D_x = 1.777 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 17.4839 (5) Å	Cell parameters from 5179 reflections
b = 8.2993 (3) Å	θ = 2.7–22.8°
c = 21.5120 (7) Å	µ = 5.41 mm⁻¹
β = 106.115 (2)°	T = 296 K
V = 2998.83 (17) Å³	Hexagonal prisms, colourless
Z = 8	0.14 × 0.13 × 0.13 mm

Data collection top

Bruker Kappa APEXII area-detector diffractometer	3997 reflections with I > 2σ(I)
ω– and φ–scans	R_int = 0.053
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θ_max = 27.8°, θ_min = 2.7°
T_min = 0.224, T_max = 0.294	h = −22→22
32806 measured reflections	k = −10→10
6995 independent reflections	l = −28→27

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.043	w = 1/[σ²(F_o²) + (0.0333P)² + 1.282P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.091	(Δ/σ)_max = 0.001
S = 1.02	Δρ_max = 0.83 e Å⁻³
6995 reflections	Δρ_min = −0.65 e Å⁻³
362 parameters	Extinction correction: SHELXL2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00111 (12)
Primary atom site location: inferred from neighbouring sites

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
C1A	0.8852 (2)	0.3745 (4)	0.38724 (16)	0.0370 (9)
H1A	0.900973	0.406568	0.348719	0.044*
C2A	0.9420 (2)	0.2461 (5)	0.42647 (17)	0.0449 (10)
H2A	0.959259	0.280858	0.471765	0.054*
C3A	0.8874 (2)	0.0992 (5)	0.42168 (18)	0.0482 (10)
H3A	0.907172	0.020343	0.456328	0.058*
C4A	0.8625 (2)	0.0245 (5)	0.35457 (19)	0.0519 (11)
H4AA	0.833459	−0.075272	0.354065	0.062*
H4AB	0.907972	0.004926	0.338033	0.062*
C5A	0.8091 (2)	0.1574 (4)	0.31692 (16)	0.0362 (9)
H5A	0.831483	0.203675	0.283872	0.043*
C6A	0.80785 (19)	0.2812 (4)	0.36906 (15)	0.0309 (8)
C7A	0.72741 (19)	0.3587 (4)	0.34938 (16)	0.0373 (9)
H7AA	0.707948	0.380283	0.386626	0.045*
H7AB	0.728396	0.458539	0.326150	0.045*
C8A	0.7213 (2)	0.1203 (5)	0.28926 (16)	0.0413 (9)
C9A	0.5932 (2)	0.2502 (5)	0.28436 (17)	0.0511 (11)
H9AA	0.574028	0.171921	0.250087	0.061*
H9AB	0.579798	0.356414	0.265650	0.061*
C10A	0.5498 (2)	0.2245 (4)	0.33480 (17)	0.0381 (9)
C11A	0.4700 (2)	0.2679 (5)	0.31950 (19)	0.0495 (10)
H11A	0.445253	0.311234	0.279045	0.059*
C12A	0.4276 (2)	0.2472 (5)	0.3638 (2)	0.0607 (12)
H12A	0.374225	0.276410	0.353302	0.073*
C13A	0.4637 (3)	0.1837 (5)	0.4234 (2)	0.0606 (12)
H13A	0.434686	0.168605	0.453196	0.073*
C14A	0.5425 (3)	0.1423 (5)	0.4392 (2)	0.0573 (11)
H14A	0.567212	0.100717	0.479959	0.069*
C15A	0.5855 (2)	0.1619 (5)	0.39485 (17)	0.0454 (10)
H15A	0.638886	0.132644	0.405694	0.055*
N1A	0.67922 (17)	0.2373 (4)	0.30754 (13)	0.0413 (8)
O1A	0.81551 (14)	0.1790 (3)	0.42508 (10)	0.0424 (6)
O2A	0.69344 (17)	0.0056 (3)	0.25485 (13)	0.0602 (8)
Br1A	0.87859 (2)	0.56161 (5)	0.44107 (2)	0.05631 (15)
Br2A	1.03562 (3)	0.20912 (6)	0.39717 (3)	0.07454 (18)
C1B	0.7908 (2)	0.1347 (4)	0.61250 (16)	0.0372 (9)
H1B	0.829984	0.094825	0.651364	0.045*
C2B	0.8272 (2)	0.2662 (5)	0.57905 (17)	0.0440 (10)
H2B	0.815399	0.240013	0.532932	0.053*
C3B	0.7797 (2)	0.4175 (5)	0.58646 (19)	0.0520 (11)
H3B	0.780526	0.501711	0.554716	0.062*
C4B	0.7985 (3)	0.4797 (5)	0.6555 (2)	0.0576 (12)
H4BA	0.772113	0.581506	0.657849	0.069*
H4BB	0.855305	0.491715	0.674785	0.069*
C5B	0.7640 (2)	0.3436 (4)	0.68693 (16)	0.0379 (9)
H5B	0.806381	0.287933	0.719270	0.045*
C6B	0.7267 (2)	0.2315 (4)	0.63022 (15)	0.0342 (8)
C7B	0.6560 (2)	0.1563 (5)	0.64522 (17)	0.0435 (9)
H7BA	0.612042	0.144230	0.606419	0.052*
H7BB	0.669218	0.051786	0.665507	0.052*
C8B	0.6947 (2)	0.3797 (5)	0.71379 (18)	0.0454 (10)
C9B	0.5654 (2)	0.2577 (6)	0.71072 (19)	0.0575 (12)
H9BA	0.568277	0.335108	0.745061	0.069*
H9BB	0.564186	0.150991	0.728853	0.069*
C10B	0.4888 (2)	0.2840 (4)	0.65875 (18)	0.0419 (9)
C11B	0.4196 (2)	0.2234 (5)	0.6684 (2)	0.0561 (11)
H11B	0.421680	0.166181	0.705987	0.067*
C12B	0.3474 (3)	0.2465 (6)	0.6231 (3)	0.0698 (14)
H12B	0.301036	0.205823	0.630294	0.084*
C13B	0.3441 (3)	0.3291 (6)	0.5677 (3)	0.0691 (14)
H13B	0.295513	0.343200	0.536779	0.083*
C14B	0.4122 (3)	0.3918 (5)	0.5572 (2)	0.0618 (12)
H14B	0.409600	0.449397	0.519547	0.074*
C15B	0.4852 (2)	0.3686 (5)	0.60312 (19)	0.0509 (10)
H15B	0.531509	0.410312	0.596131	0.061*
N1B	0.63674 (18)	0.2718 (4)	0.68980 (14)	0.0465 (8)
O1B	0.70287 (14)	0.3452 (3)	0.57735 (11)	0.0503 (7)
O2B	0.69187 (17)	0.4868 (4)	0.75178 (14)	0.0648 (8)
Br1B	0.74753 (3)	−0.04142 (6)	0.55333 (2)	0.06418 (16)
Br2B	0.94187 (2)	0.28604 (6)	0.61425 (2)	0.06177 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.037 (2)	0.040 (2)	0.036 (2)	−0.0011 (18)	0.0147 (17)	−0.0043 (17)
C2A	0.038 (2)	0.055 (3)	0.039 (2)	0.0064 (19)	0.0054 (18)	−0.0034 (19)
C3A	0.046 (2)	0.048 (2)	0.048 (2)	0.008 (2)	0.008 (2)	0.013 (2)
C4A	0.052 (3)	0.039 (2)	0.065 (3)	−0.002 (2)	0.017 (2)	−0.010 (2)
C5A	0.037 (2)	0.039 (2)	0.035 (2)	−0.0019 (17)	0.0145 (17)	−0.0052 (17)
C6A	0.0317 (19)	0.037 (2)	0.0262 (18)	0.0007 (17)	0.0116 (15)	0.0010 (16)
C7A	0.034 (2)	0.043 (2)	0.038 (2)	−0.0003 (18)	0.0151 (17)	−0.0061 (18)
C8A	0.047 (2)	0.051 (3)	0.027 (2)	−0.010 (2)	0.0127 (18)	−0.0056 (19)
C9A	0.034 (2)	0.074 (3)	0.039 (2)	−0.003 (2)	0.0010 (18)	0.004 (2)
C10A	0.031 (2)	0.042 (2)	0.039 (2)	−0.0070 (17)	0.0072 (17)	−0.0031 (18)
C11A	0.038 (2)	0.056 (3)	0.051 (2)	−0.004 (2)	0.005 (2)	−0.001 (2)
C12A	0.038 (2)	0.059 (3)	0.088 (4)	−0.004 (2)	0.022 (3)	−0.009 (3)
C13A	0.061 (3)	0.065 (3)	0.068 (3)	−0.016 (3)	0.038 (3)	−0.014 (3)
C14A	0.061 (3)	0.066 (3)	0.045 (3)	−0.011 (2)	0.015 (2)	0.002 (2)
C15A	0.038 (2)	0.055 (3)	0.043 (2)	−0.0004 (19)	0.0104 (19)	0.0004 (19)
N1A	0.0313 (16)	0.058 (2)	0.0347 (17)	−0.0048 (15)	0.0094 (14)	−0.0095 (15)
O1A	0.0450 (15)	0.0525 (16)	0.0315 (14)	−0.0023 (13)	0.0140 (12)	0.0063 (12)
O2A	0.0576 (19)	0.071 (2)	0.0518 (17)	−0.0166 (16)	0.0157 (15)	−0.0287 (15)
Br1A	0.0431 (2)	0.0517 (3)	0.0735 (3)	−0.0083 (2)	0.0150 (2)	−0.0237 (2)
Br2A	0.0425 (3)	0.0729 (3)	0.1129 (4)	0.0071 (2)	0.0293 (3)	−0.0161 (3)
C1B	0.034 (2)	0.045 (2)	0.0293 (19)	−0.0019 (18)	0.0033 (16)	−0.0069 (17)
C2B	0.033 (2)	0.066 (3)	0.032 (2)	−0.0049 (19)	0.0068 (17)	−0.0002 (19)
C3B	0.049 (3)	0.055 (3)	0.052 (3)	0.004 (2)	0.014 (2)	0.019 (2)
C4B	0.057 (3)	0.039 (2)	0.079 (3)	−0.003 (2)	0.021 (2)	−0.007 (2)
C5B	0.0310 (19)	0.045 (2)	0.034 (2)	0.0007 (17)	0.0029 (16)	−0.0066 (17)
C6B	0.0319 (19)	0.041 (2)	0.0261 (19)	0.0007 (17)	0.0029 (15)	0.0007 (16)
C7B	0.031 (2)	0.054 (3)	0.042 (2)	−0.0040 (18)	0.0058 (17)	−0.0103 (19)
C8B	0.039 (2)	0.059 (3)	0.034 (2)	0.008 (2)	0.0017 (18)	−0.004 (2)
C9B	0.041 (2)	0.088 (3)	0.048 (2)	0.003 (2)	0.019 (2)	0.005 (2)
C10B	0.038 (2)	0.041 (2)	0.049 (2)	0.0043 (19)	0.0166 (19)	−0.0047 (19)
C11B	0.046 (3)	0.051 (3)	0.077 (3)	0.005 (2)	0.027 (2)	0.004 (2)
C12B	0.038 (3)	0.062 (3)	0.112 (4)	−0.002 (2)	0.024 (3)	−0.010 (3)
C13B	0.043 (3)	0.068 (3)	0.085 (4)	0.016 (2)	−0.001 (3)	−0.026 (3)
C14B	0.076 (3)	0.054 (3)	0.053 (3)	0.017 (3)	0.014 (3)	−0.005 (2)
C15B	0.046 (3)	0.057 (3)	0.051 (3)	−0.002 (2)	0.016 (2)	−0.004 (2)
N1B	0.0353 (18)	0.069 (2)	0.0368 (18)	−0.0002 (17)	0.0119 (15)	−0.0119 (17)
O1B	0.0382 (15)	0.0691 (19)	0.0386 (15)	0.0098 (14)	0.0022 (12)	0.0128 (13)
O2B	0.0585 (19)	0.078 (2)	0.0557 (18)	0.0063 (16)	0.0126 (15)	−0.0312 (16)
Br1B	0.0532 (3)	0.0681 (3)	0.0736 (3)	−0.0076 (2)	0.0215 (2)	−0.0344 (2)
Br2B	0.0391 (2)	0.0748 (3)	0.0719 (3)	−0.0073 (2)	0.0161 (2)	0.0053 (2)

Geometric parameters (Å, º) top

C1A—C6A	1.513 (5)	C1B—C6B	1.512 (5)
C1A—C2A	1.539 (5)	C1B—C2B	1.539 (5)
C1A—Br1A	1.959 (3)	C1B—Br1B	1.948 (3)
C1A—H1A	0.9800	C1B—H1B	0.9800
C2A—C3A	1.534 (5)	C2B—C3B	1.538 (5)
C2A—Br2A	1.935 (4)	C2B—Br2B	1.943 (3)
C2A—H2A	0.9800	C2B—H2B	0.9800
C3A—O1A	1.440 (4)	C3B—O1B	1.434 (4)
C3A—C4A	1.520 (5)	C3B—C4B	1.520 (5)
C3A—H3A	0.9800	C3B—H3B	0.9800
C4A—C5A	1.525 (5)	C4B—C5B	1.524 (5)
C4A—H4AA	0.9700	C4B—H4BA	0.9700
C4A—H4AB	0.9700	C4B—H4BB	0.9700
C5A—C8A	1.516 (5)	C5B—C8B	1.510 (5)
C5A—C6A	1.526 (4)	C5B—C6B	1.529 (4)
C5A—H5A	0.9800	C5B—H5B	0.9800
C6A—O1A	1.449 (4)	C6B—O1B	1.447 (4)
C6A—C7A	1.497 (4)	C6B—C7B	1.497 (5)
C7A—N1A	1.455 (4)	C7B—N1B	1.459 (4)
C7A—H7AA	0.9700	C7B—H7BA	0.9700
C7A—H7AB	0.9700	C7B—H7BB	0.9700
C8A—O2A	1.221 (4)	C8B—O2B	1.218 (4)
C8A—N1A	1.341 (5)	C8B—N1B	1.343 (5)
C9A—N1A	1.452 (4)	C9B—N1B	1.443 (4)
C9A—C10A	1.501 (5)	C9B—C10B	1.504 (5)
C9A—H9AA	0.9700	C9B—H9BA	0.9700
C9A—H9AB	0.9700	C9B—H9BB	0.9700
C10A—C15A	1.371 (5)	C10B—C15B	1.374 (5)
C10A—C11A	1.389 (5)	C10B—C11B	1.378 (5)
C11A—C12A	1.371 (5)	C11B—C12B	1.377 (6)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.368 (6)	C12B—C13B	1.362 (6)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.369 (6)	C13B—C14B	1.374 (6)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.377 (5)	C14B—C15B	1.394 (5)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300

C6A—C1A—C2A	100.4 (3)	C6B—C1B—C2B	100.0 (3)
C6A—C1A—Br1A	111.3 (2)	C6B—C1B—Br1B	112.5 (2)
C2A—C1A—Br1A	111.1 (2)	C2B—C1B—Br1B	111.3 (2)
C6A—C1A—H1A	111.2	C6B—C1B—H1B	110.9
C2A—C1A—H1A	111.2	C2B—C1B—H1B	110.9
Br1A—C1A—H1A	111.2	Br1B—C1B—H1B	110.9
C3A—C2A—C1A	102.6 (3)	C3B—C2B—C1B	103.0 (3)
C3A—C2A—Br2A	114.8 (3)	C3B—C2B—Br2B	114.8 (3)
C1A—C2A—Br2A	114.0 (2)	C1B—C2B—Br2B	113.2 (2)
C3A—C2A—H2A	108.4	C3B—C2B—H2B	108.5
C1A—C2A—H2A	108.4	C1B—C2B—H2B	108.5
Br2A—C2A—H2A	108.4	Br2B—C2B—H2B	108.5
O1A—C3A—C4A	102.3 (3)	O1B—C3B—C4B	102.4 (3)
O1A—C3A—C2A	99.6 (3)	O1B—C3B—C2B	99.0 (3)
C4A—C3A—C2A	113.4 (3)	C4B—C3B—C2B	113.7 (3)
O1A—C3A—H3A	113.4	O1B—C3B—H3B	113.4
C4A—C3A—H3A	113.4	C4B—C3B—H3B	113.4
C2A—C3A—H3A	113.4	C2B—C3B—H3B	113.4
C3A—C4A—C5A	100.4 (3)	C3B—C4B—C5B	100.2 (3)
C3A—C4A—H4AA	111.7	C3B—C4B—H4BA	111.7
C5A—C4A—H4AA	111.7	C5B—C4B—H4BA	111.7
C3A—C4A—H4AB	111.7	C3B—C4B—H4BB	111.7
C5A—C4A—H4AB	111.7	C5B—C4B—H4BB	111.7
H4AA—C4A—H4AB	109.5	H4BA—C4B—H4BB	109.5
C8A—C5A—C4A	117.8 (3)	C8B—C5B—C4B	118.7 (3)
C8A—C5A—C6A	101.9 (3)	C8B—C5B—C6B	102.4 (3)
C4A—C5A—C6A	103.2 (3)	C4B—C5B—C6B	103.3 (3)
C8A—C5A—H5A	111.1	C8B—C5B—H5B	110.5
C4A—C5A—H5A	111.1	C4B—C5B—H5B	110.5
C6A—C5A—H5A	111.1	C6B—C5B—H5B	110.5
O1A—C6A—C7A	110.5 (3)	O1B—C6B—C7B	111.5 (3)
O1A—C6A—C1A	102.4 (3)	O1B—C6B—C1B	102.7 (3)
C7A—C6A—C1A	123.7 (3)	C7B—C6B—C1B	123.2 (3)
O1A—C6A—C5A	101.6 (3)	O1B—C6B—C5B	101.3 (3)
C7A—C6A—C5A	106.6 (3)	C7B—C6B—C5B	106.1 (3)
C1A—C6A—C5A	109.9 (3)	C1B—C6B—C5B	110.0 (3)
N1A—C7A—C6A	102.4 (3)	N1B—C7B—C6B	102.9 (3)
N1A—C7A—H7AA	111.3	N1B—C7B—H7BA	111.2
C6A—C7A—H7AA	111.3	C6B—C7B—H7BA	111.2
N1A—C7A—H7AB	111.3	N1B—C7B—H7BB	111.2
C6A—C7A—H7AB	111.3	C6B—C7B—H7BB	111.2
H7AA—C7A—H7AB	109.2	H7BA—C7B—H7BB	109.1
O2A—C8A—N1A	125.7 (4)	O2B—C8B—N1B	125.3 (4)
O2A—C8A—C5A	125.9 (3)	O2B—C8B—C5B	126.0 (4)
N1A—C8A—C5A	108.4 (3)	N1B—C8B—C5B	108.7 (3)
N1A—C9A—C10A	115.1 (3)	N1B—C9B—C10B	115.1 (3)
N1A—C9A—H9AA	108.5	N1B—C9B—H9BA	108.5
C10A—C9A—H9AA	108.5	C10B—C9B—H9BA	108.5
N1A—C9A—H9AB	108.5	N1B—C9B—H9BB	108.5
C10A—C9A—H9AB	108.5	C10B—C9B—H9BB	108.5
H9AA—C9A—H9AB	107.5	H9BA—C9B—H9BB	107.5
C15A—C10A—C11A	119.0 (3)	C15B—C10B—C11B	119.2 (4)
C15A—C10A—C9A	123.1 (3)	C15B—C10B—C9B	122.5 (3)
C11A—C10A—C9A	117.9 (3)	C11B—C10B—C9B	118.3 (4)
C12A—C11A—C10A	120.3 (4)	C12B—C11B—C10B	120.9 (4)
C12A—C11A—H11A	119.9	C12B—C11B—H11B	119.6
C10A—C11A—H11A	119.9	C10B—C11B—H11B	119.6
C13A—C12A—C11A	120.2 (4)	C13B—C12B—C11B	119.8 (4)
C13A—C12A—H12A	119.9	C13B—C12B—H12B	120.1
C11A—C12A—H12A	119.9	C11B—C12B—H12B	120.1
C12A—C13A—C14A	120.0 (4)	C12B—C13B—C14B	120.5 (4)
C12A—C13A—H13A	120.0	C12B—C13B—H13B	119.8
C14A—C13A—H13A	120.0	C14B—C13B—H13B	119.8
C13A—C14A—C15A	120.2 (4)	C13B—C14B—C15B	119.7 (4)
C13A—C14A—H14A	119.9	C13B—C14B—H14B	120.2
C15A—C14A—H14A	119.9	C15B—C14B—H14B	120.2
C10A—C15A—C14A	120.3 (4)	C10B—C15B—C14B	120.0 (4)
C10A—C15A—H15A	119.8	C10B—C15B—H15B	120.0
C14A—C15A—H15A	119.8	C14B—C15B—H15B	120.0
C8A—N1A—C9A	123.6 (3)	C8B—N1B—C9B	124.0 (3)
C8A—N1A—C7A	114.4 (3)	C8B—N1B—C7B	113.8 (3)
C9A—N1A—C7A	121.9 (3)	C9B—N1B—C7B	121.9 (3)
C3A—O1A—C6A	96.2 (2)	C3B—O1B—C6B	96.4 (2)

C6A—C1A—C2A—C3A	2.0 (3)	C6B—C1B—C2B—C3B	2.6 (3)
Br1A—C1A—C2A—C3A	119.8 (3)	Br1B—C1B—C2B—C3B	121.6 (3)
C6A—C1A—C2A—Br2A	126.7 (2)	C6B—C1B—C2B—Br2B	127.1 (2)
Br1A—C1A—C2A—Br2A	−115.4 (2)	Br1B—C1B—C2B—Br2B	−113.9 (2)
C1A—C2A—C3A—O1A	−37.2 (3)	C1B—C2B—C3B—O1B	−37.7 (3)
Br2A—C2A—C3A—O1A	−161.4 (2)	Br2B—C2B—C3B—O1B	−161.2 (2)
C1A—C2A—C3A—C4A	70.7 (4)	C1B—C2B—C3B—C4B	70.2 (4)
Br2A—C2A—C3A—C4A	−53.5 (4)	Br2B—C2B—C3B—C4B	−53.2 (4)
O1A—C3A—C4A—C5A	37.9 (3)	O1B—C3B—C4B—C5B	37.9 (4)
C2A—C3A—C4A—C5A	−68.4 (4)	C2B—C3B—C4B—C5B	−67.9 (4)
C3A—C4A—C5A—C8A	−114.6 (3)	C3B—C4B—C5B—C8B	−116.0 (3)
C3A—C4A—C5A—C6A	−3.4 (4)	C3B—C4B—C5B—C6B	−3.5 (4)
C2A—C1A—C6A—O1A	33.9 (3)	C2B—C1B—C6B—O1B	33.4 (3)
Br1A—C1A—C6A—O1A	−83.8 (3)	Br1B—C1B—C6B—O1B	−84.7 (3)
C2A—C1A—C6A—C7A	159.2 (3)	C2B—C1B—C6B—C7B	160.0 (3)
Br1A—C1A—C6A—C7A	41.5 (4)	Br1B—C1B—C6B—C7B	41.9 (4)
C2A—C1A—C6A—C5A	−73.4 (3)	C2B—C1B—C6B—C5B	−73.8 (3)
Br1A—C1A—C6A—C5A	168.9 (2)	Br1B—C1B—C6B—C5B	168.1 (2)
C8A—C5A—C6A—O1A	91.0 (3)	C8B—C5B—C6B—O1B	92.6 (3)
C4A—C5A—C6A—O1A	−31.6 (3)	C4B—C5B—C6B—O1B	−31.4 (3)
C8A—C5A—C6A—C7A	−24.7 (3)	C8B—C5B—C6B—C7B	−24.0 (4)
C4A—C5A—C6A—C7A	−147.3 (3)	C4B—C5B—C6B—C7B	−147.9 (3)
C8A—C5A—C6A—C1A	−161.1 (3)	C8B—C5B—C6B—C1B	−159.3 (3)
C4A—C5A—C6A—C1A	76.3 (3)	C4B—C5B—C6B—C1B	76.8 (3)
O1A—C6A—C7A—N1A	−86.1 (3)	O1B—C6B—C7B—N1B	−86.1 (3)
C1A—C6A—C7A—N1A	152.2 (3)	C1B—C6B—C7B—N1B	151.2 (3)
C5A—C6A—C7A—N1A	23.4 (3)	C5B—C6B—C7B—N1B	23.4 (4)
C4A—C5A—C8A—O2A	−52.9 (5)	C4B—C5B—C8B—O2B	−52.6 (5)
C6A—C5A—C8A—O2A	−164.9 (3)	C6B—C5B—C8B—O2B	−165.6 (4)
C4A—C5A—C8A—N1A	128.8 (3)	C4B—C5B—C8B—N1B	128.6 (4)
C6A—C5A—C8A—N1A	16.8 (4)	C6B—C5B—C8B—N1B	15.6 (4)
N1A—C9A—C10A—C15A	−12.7 (5)	N1B—C9B—C10B—C15B	−22.1 (6)
N1A—C9A—C10A—C11A	166.8 (3)	N1B—C9B—C10B—C11B	159.4 (4)
C15A—C10A—C11A—C12A	−0.5 (6)	C15B—C10B—C11B—C12B	0.1 (6)
C9A—C10A—C11A—C12A	−179.9 (4)	C9B—C10B—C11B—C12B	178.7 (4)
C10A—C11A—C12A—C13A	0.0 (6)	C10B—C11B—C12B—C13B	0.5 (7)
C11A—C12A—C13A—C14A	0.7 (6)	C11B—C12B—C13B—C14B	−1.0 (7)
C12A—C13A—C14A—C15A	−1.0 (6)	C12B—C13B—C14B—C15B	0.9 (6)
C11A—C10A—C15A—C14A	0.1 (6)	C11B—C10B—C15B—C14B	−0.2 (6)
C9A—C10A—C15A—C14A	179.6 (4)	C9B—C10B—C15B—C14B	−178.8 (4)
C13A—C14A—C15A—C10A	0.6 (6)	C13B—C14B—C15B—C10B	−0.3 (6)
O2A—C8A—N1A—C9A	−5.0 (6)	O2B—C8B—N1B—C9B	−6.4 (6)
C5A—C8A—N1A—C9A	173.3 (3)	C5B—C8B—N1B—C9B	172.4 (3)
O2A—C8A—N1A—C7A	179.3 (3)	O2B—C8B—N1B—C7B	−179.9 (4)
C5A—C8A—N1A—C7A	−2.4 (4)	C5B—C8B—N1B—C7B	−1.0 (4)
C10A—C9A—N1A—C8A	113.6 (4)	C10B—C9B—N1B—C8B	119.8 (4)
C10A—C9A—N1A—C7A	−71.0 (4)	C10B—C9B—N1B—C7B	−67.2 (5)
C6A—C7A—N1A—C8A	−13.4 (4)	C6B—C7B—N1B—C8B	−14.3 (4)
C6A—C7A—N1A—C9A	170.8 (3)	C6B—C7B—N1B—C9B	172.0 (3)
C4A—C3A—O1A—C6A	−58.3 (3)	C4B—C3B—O1B—C6B	−58.5 (3)
C2A—C3A—O1A—C6A	58.3 (3)	C2B—C3B—O1B—C6B	58.4 (3)
C7A—C6A—O1A—C3A	167.7 (3)	C7B—C6B—O1B—C3B	167.3 (3)
C1A—C6A—O1A—C3A	−58.7 (3)	C1B—C6B—O1B—C3B	−59.0 (3)
C5A—C6A—O1A—C3A	54.9 (3)	C5B—C6B—O1B—C3B	54.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1A—H1A···O2Aⁱ	0.98	2.51	3.175 (4)	125
C4A—H4AB···Br2A	0.97	2.81	3.287 (4)	111
C5A—H5A···O2Aⁱ	0.98	2.64	3.271 (4)	123
C7A—H7AB···O2Aⁱ	0.97	2.53	3.186 (4)	125
C1B—H1B···O2Bⁱⁱ	0.98	2.39	3.104 (4)	129
C2B—H2B···O1A	0.98	2.38	3.341 (4)	168
C4B—H4BB···Br2B	0.97	2.83	3.301 (4)	111
C5B—H5B···O2Bⁱⁱ	0.98	2.57	3.247 (5)	126
C7B—H7BB···O2Bⁱⁱ	0.97	2.64	3.270 (5)	123

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+3/2.

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

Contact	Distance	Symmetry operation
H2A···Br1A	3.21	2 - x, 1 - y, 1 - z
Br1A···Br2B	3.8655	2 - x, 1 - y, 1 - z
Br2A···Br1B	3.8993	2 - x, -y, 1 - z
O1A···H2B	2.38	x, y, z
O2A···H1A	2.51	3/2 - x, -1/2 + y, 1/2 - z
O2A···H11B	2.78	1 - x, - y, 1 - z
H7AA···C13B	2.85	1 - x, 1 - y, 1 - z
H11A···H5B	2.55	-1/2 + x, 1/2 - y, -1/2 + z
H13B···Br1B	3.13	1 - x, -y, 1 - z
O2B···H1B	2.39	3/2 - x, 1/2 + y, 3/2 - z
H13B···H3B	2.42	1 - x, 1 - y, 1 - z

Percentage contributions of interatomic contacts to the Hirshfeld surface for the title compound top

Contact	Percentage contribution
H···H	44.6
Br···H/H···Br	24.1
O···H/H···O	13.5
C···H/H···C	11.2
Br···Br	3.9
C···C	2.0
N···H/H···N	0.5
Br···C/C···Br	0.3

Funding information

The authors are grateful to the Russian Foundation for Basic Research (RFBR) (award No. 19–03-00807) for financial support of this research.

References

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