(3aS,4R,5R,6S,7aR)-4,5-Di­bromo-2-[4-(tri­fluoro­meth­yl)phen­yl]-2,3,3a,4,5,6,7,7a-octa­hydro-3a,6-ep­oxy-1H-isoindol-1-one: crystal structure and Hirshfeld surface analysis

Mertsalov, D.F.; Alekseeva, K.A.; Daria, M.S.; Cheshigin, M.E.; Çelikesir, S.T.; Akkurt, M.; Grigoriev, M.S.; Mlowe, S.

doi:10.1107/S2056989021003200

research communications

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 77| Part 5| May 2021| Pages 466-472

https://doi.org/10.1107/S2056989021003200

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(3aS,4R,5R,6S,7aR)-4,5-Dibromo-2-[4-(trifluoromethyl)phenyl]-2,3,3a,4,5,6,7,7a-octahydro-3a,6-epoxy-1H-isoindol-1-one: crystal structure and Hirshfeld surface analysis

Dmitriy F. Mertsalov,^a Kseniia A. Alekseeva,^a Magrycheva S. Daria,^a Maxim E. Cheshigin,^a Sevim Türktekin Çelikesir,^b Mehmet Akkurt,^b Mikhail S. Grigoriev ^c and Sixberth Mlowe ^d ^*

^aDepartment of Organic Chemistry, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., 117198, Moscow, Russian Federation, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cFrumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninskiy prospect 31-4, Moscow 119071, Russian Federation, 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 A. Briceno, Venezuelan Institute of Scientific Research, Venezuela (Received 12 March 2021; accepted 26 March 2021; online 9 April 2021)

The asymmetric unit of the title compound, C₁₅H₁₂Br₂F₃NO₂, consists of two crystallographically independent molecules. In both molecules, the pyrrolidine and tetrahydrofuran rings adopt an envelope conformation. In the crystal, molecule pairs generate centrosymmetric rings with R²₂(8) motifs linked by C—H⋯O hydrogen bonds. These pairs of molecules form a tetrameric supramolecular motif, leading to molecular layers parallel to the (100) plane by C—H⋯π and C—Br⋯π interactions. Interlayer van der Waals and interhalogen interactions stabilize molecular packing. The F atoms of the CF₃ groups of both molecules are disordered over two sets of sites with refined site occupancies of 0.60 (3)/0.40 (3) and 0.640 (15)/0.360 (15). The most important contributions to the surface contacts of both molecules are from H⋯H (23.8 and 22.4%), Br⋯H/H⋯Br (18.3 and 12.3%), O⋯H/H⋯O (14.3 and 9.7%) and F⋯H/H⋯F (10.4 and 19.1%) interactions, as concluded from a Hirshfeld surface analysis.

Keywords: crystal structure; epoxyisoindole group; hydrogen bond; halogen bond; non-covalent interactions; Hirshfeld surface analysis.

CCDC reference: 2036842

1. Chemical context

Isoindoles are important structural units in many natural products and are widely used as drugs and as building-blocks for the construction of new N-containing heterocyclic compounds and functional materials (Nadirova et al., 2019 ; Zubkov et al., 2011 , 2014 , 2018 ). The biological and physical properties of N-heterocycles are dependent on the attached functional groups (Grudova et al., 2020 ; Zaytsev et al., 2017 , 2019 , 2020 ; Asgarova et al., 2019 ; Khalilov et al., 2011 ; Yin et al., 2020 ). Thus, the functionalization of isoindole moieties with non-covalent bond donor/acceptor sites can improve their biological and photophysical properties as well as coordination ability (Wicholas et al., 2006 ).

On the other hand, non-covalent interactions, such as hydrogen, aerogen, halogen, chalcogen, pnictogen, tetrel and icosagen bonds, as well as n–π*, π–π stacking, π–cation, π–anion and hydrophobic interactions have also attracted much attention recently and have been demonstrated to play a prominent role in synthesis, catalysis, supramolecular chemistry, molecular recognition, biological systems and functional materials (Asadov et al., 2016 ; Gurbanov et al., 2017 , 2018 , 2020 ; Karmakar et al., 2017 ; Kopylovich et al., 2011 ; Ma et al., 2017a ,b ; 2020 ; Mahmudov et al., 2010 , 2012 , 2013 , 2019 , 2020 ; Mizar et al., 2012 ; Sutradhar et al., 2015 , 2016 ). Halogen bonding is a rather spread phenomenon since halogen atoms or ions can form short non-bonded contacts with electron acceptors, electron donors or be interconnected due to anisotropic charge distribution in halogen atoms (Afkhami et al., 2017 ; Maharramov et al., 2018 , 2019 ; Mahmoudi et al., 2017 , 2019 ; Shixaliyev et al., 2014 ). In fact, attachment of isoindoles with non-covalent bond donor or acceptor sites can affect their supramolecular arrangements significantly (Gurbanov et al., 2021 ).

In a continuation of our work in this direction, we have functionalized a new isoindole, (3aS,4R,5R,6S,7aR)-4,5-dibromo-2-[4-(trifluoromethyl)phenyl]-2,3,3a,4,5,6,7,7a-octahydro-3a,6-epoxy-1H-isoindol-1-one (1; Fig. 1), which provides C—Br⋯π halogen bonds as well as C—H⋯O and C—H⋯π types of intermolecular hydrogen bonds.

Figure 1
Synthesis of (3aS,4R,5R,6S,7aR)-4,5-dibromo-2-[4-(trifluoromethyl)phenyl]-2,3,3a,4,5,6,7,7a-octahydro-3a,6-epoxy-1H-isoindol-1-one (1).

2. Structural commentary

The asymmetric unit of the title compound (Fig. 2) contains two crystallographically molecules of similar shape, hereafter referred to as molecules A (including atom C1) and B (including atom C21). 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 0.278 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. Hydrogen atoms are shown as spheres of arbitrary radius. The minor components of the disordered CF₃ groups were omitted for clarity.

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 (N2/C1/C3/C3A/C7A and N22/C21/C23/C23A/C27A), tetrahydrofuran rings (O8/C3A/C4–C6, O8/C3A/C6/C7/C7A and O28/C23A/C24–C26, O28/C23A/C26/C27/C27A) and six-membered rings (C3A/C4–C7/C7A and C23A/C24–C27/C27A), which generate epoxyisoindole moieties (O8/ N2/C1/C3/C3A/C4–C7/C7A and O28/ N22/C21/C23/C23A/C24–C27/C27A), are puckered. In molecules A and B, both tetrahydrofuran rings adopt an envelope conformation with puckering parameters (Cremer & Pople, 1975 ) Q(2) = 0.580 (3) Å, φ(2) = 176.3 (4)° for A (O8/C3A/C4–C6), Q(2) = 0.547 (3) Å, φ(2) = 357.4 (4)° for A (O8/C3A/C6/C7/C7A), and Q(2) = 0.580 (3) Å, φ(2) = 180.3 (4)° for B (O28/C23A/C24–C26) and Q(2) = 0.554 (3) Å, φ(2) = 354.2 (4)° for B (O28/C23A/C26/C27/C27A). The five-membered pyrrolidine rings also exhibit an envelope conformation, with a maximum deviation from the mean plane of 0.165 (3) Å at C3A [puckering parameters Q(2) = 0.262 (4) Å, φ(2) = 281.8 (8)°] for molecule A and 0.156 (3) Å at C23A [puckering parameters Q(2) = 0.248 (4) Å, φ(2) = 291.3 (8)°] for molecule B. In both molecules, the six-membered ring has a boat conformation [Q_T = 0.925 (4) Å, θ = 92.2 (2)°, φ = 180.5 (2)° for molecule A; Q_T = 0.924 (4) Å, θ = 91.7 (2)°, φ = 177.1 (2)° for molecule B].

3. Supramolecular features

In the crystal, molecules generate centrosymmetric dimers described by $[R_{2}^{2}]$ (8) motifs (Bernstein et al., 1995 ) by C—H⋯O hydrogen bonds (Table 1). These pairs of molecules form a tetrameric supramolecular motif, by self-complementary C—H⋯π connections (Fig. 4). Additionally, these building units are self-assembled via C—Br⋯π interactions, generating a two-dimensional supramolecular network parallel to the (100) plane (Fig. 5). Interlayer van der Waals and interhalogen interactions stabilize molecular packing.

Table 1
Hydrogen-bond geometry (Å, °)

Cg5 and Cg10 are the centroids of the C11–C16 and C31–C36 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O8ⁱ	0.98	2.57	3.342 (4)	135
C7—H7A⋯Br2	0.97	2.82	3.300 (4)	112
C16—H16A⋯O1	0.93	2.26	2.853 (4)	121
C27—H27A⋯Br22	0.97	2.78	3.259 (4)	111
C36—H36A⋯O21	0.93	2.28	2.856 (5)	120
C7A—H7AA⋯Cg10ⁱ	0.98	2.94	3.741 (4)	139
C27A—H27C⋯Cg5ⁱ	0.98	2.97	3.924 (4)	166
Symmetry code: (i) .

Figure 4
A view of the intermolecular C—H⋯O hydrogen bonds and C—H⋯π and C—Br⋯π interactions in the unit cell of the title compound. Only the major components of the disordered CF₃ groups are shown. [Symmetry codes: (a) 1 − x, 1 − y, 1 − z; (b) − 1 + x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z].

Figure 5
A view of the molecular packing of the title compound along the a axis. Only the major components of the disordered CF₃ groups are shown.

4. Hirshfeld surface analysis

For both molecules A and B, the intermolecular interactions (Table 2) were quantified using Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ) and the associated two-dimensional fingerprint plots (McKinnon et al., 2007 ) generated. The calculations and visualization were performed using CrystalExplorer17 (Turner et al., 2017 ). Fig. 6 shows the Hirshfeld surface of the title compound mapped over d_norm in a fixed color scale of −0.2089 (red) to +1.1825 (blue) arbitrary units for molecule A and −0.2105 (red) to +1.2372 (blue) arbitrary units for molecule B, where the red spots indicate the intermolecular contacts shorter than the van der Waals separations. Fig. 7 shows the full two-dimensional fingerprint plot (Fig. 7a) and those delineated into the major contacts: H⋯H (23.8% for molecule A and 22.4% for molecule B, Fig. 7b) interactions are the major factor in the crystal packing with Br⋯H/H⋯Br (18.3% for molecule A and 12.3% for molecule B, Fig.7c), O⋯H/H⋯O (14.3% for molecule A and 9.7% for molecule B, Fig. 7d) and F⋯H/H⋯F (10.4% for molecule A and 19.1% for molecule B, Fig. 7e) interactions representing the next highest contributions. The percentage contributions of other weak interactions are listed in Table 3. The fact that the same interactions make different contributions to the HS molecules A and B can be attributed to the different molecular environments of the A and B molecules in the crystalline structure.

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

Asterisks indicate symmetry-generated atoms

Contact	Distance	Symmetry operation
H5A⋯O8	2.57	1 − x, 1 − y, 1 − z
H3B⋯O28	2.82	x, $[{3\over 2}]$ − y, − $[{1\over 2}]$ + z
H4A⋯O1	2.74	−1 + x, y, z
Br2⋯Br22	3.74	−x, − $[{1\over 2}]$ + y, $[{3\over 2}]$ − z
Br2⋯H26A	2.95	1 − x, − $[{1\over 2}]$ + y, $[{3\over 2}]$ − z
H7AA⋯C36	2.59	1 − x, 1 − y, 1 − z
F3A⋯F23	2.90	2 − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
H15A⋯O21	2.62	2 − x, 1 − y, 1 − z
*F2A⋯H23B	2.60	1 + x, $[{3\over 2}]$ − y, − $[{1\over 2}]$ + z
H23A⋯H36A	2.49	−1 + x, y, z
H23B⋯*F2A	2.60	−1 + x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z
Br22⋯*F23	3.48	−1 + x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z
F22A⋯F1	2.94	2 − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
H33A⋯*F21A	2.84	1 − x, 2 − y, 1 − z
F22A⋯F22	3.09	2 − x, 2 − y, 1 − z

Table 3
Percentage contributions of interatomic contacts to the Hirshfeld surface for the molecules A and B of the title compound

Contact	Molecule A	Molecule B
H⋯H	23.8	22.4
Br⋯H/H⋯Br	18.3	12.3
O⋯H/H⋯O	14.3	9.7
F⋯H/H⋯F	10.4	19.1
C⋯H/H⋯C	9.9	7.8
F⋯F	6.9	8.6
Br⋯F/F⋯Br	3.9	8.0
Br⋯C/C⋯Br	3.7	3.5
Br⋯Br	2.4	1.6
F⋯C/C⋯F	2.3	2.4
Br⋯O/O⋯Br	1.4	2.1
Br⋯N/N⋯Br	1.1	0.9
O⋯N/N⋯O	0.5	0.5
O⋯C/C⋯O	0.5	0.4
C⋯C	0.3	0.3
N⋯H/H⋯N	0.2	0.3
N⋯C/C⋯N	0.1	0.1

Figure 6
Hirshfeld surfaces of molecules A and B of the title compound mapped with d_norm.

Figure 7
The two-dimensional fingerprint plots for molecules A and B of the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) F⋯H/H⋯F, (d) Br⋯H/H⋯Br and (e) 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, respectively].

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 eight hits that closely resemble the title compound, viz. 4,5-dibromo-6-methyl-2-phenylhexahydro-3a,6-epoxyisoindol-1(4H)-one (IMUBIE; Mertsalov et al., 2021a ), 2-benzyl-4,5-dibromohexahydro-3a,6-epoxyisoindol-1(4H)-one (OMEMAX; Mertsalov et al., 2021b ), (3aR,6S,7aR)-7a-chloro-2-[(4-nitrophenyl)sulfonyl]-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole (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-methyl-phenyl)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-epoxyiso-indole (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-chloroper-hydro-2,6a-epoxyoxireno(e)isoindole-5-carboxylate (MIGTIG; Koşar et al., 2007 ).

In the crystal of IMUBIE, the molecules are linked into dimers by pairs of C—H⋯O hydrogen bonds, thus generating $[R_{2}^{2}]$ (18) rings. The crystal packing is dominated by H⋯H, Br⋯H, H⋯π and Br⋯π interactions. In the crystal structures of OMEMAX, AGONUH, TIJMIK, YAXCIL, UPAQEI and ERIVIL, the molecules are linked by predominantly C—H⋯O hydrogen bonds describing different hydrogen-bonding pattern connectivities. In OMEMAX, molecules form sheets lying parallel to the (002) plane. These sheets are connected only by weak van der Waals interactions. In the crystal of AGONUH, the molecules are connected in zigzag chains running along the b-axis direction. In TIJMIK, two types of C—H⋯O hydrogen bonds are found, viz. R²₂(20) and R₄⁴(26) rings, with adjacent rings running parallel to the ac plane. Additionally, C—H⋯O hydrogen bonds form a C(6) chain, linking the molecules in the b-axis direction. In the crystal of ERIVIL, the molecules are connected into $[R_{2}^{2}]$ (8) and $[R_{2}^{2}]$ (14) rings along the b-axis direction. In MIGTIG, the molecules are linked only by weak van der Waals interactions.

6. Synthesis and crystallization

(3aS,6S,7aR)-2-(4-(Trifluoromethyl)phenyl)-2,3,7,7a-tetrahydro-3a,6-epoxyisoindol-1(6H)-one (1.2 mmol) and the brominating agent [(Me₂NCOMe)₂H]Br₃ (1.32 mmol) in 3 mL of dry chloroform were heated under reflux for 3–5 h (TLC control, EtOAc–hexane, 1:1). The reaction mixture was poured into H₂O (50 mL), extracted with CHCl₃ (3 × 20 mL) and combined organic parts were dried over anhydrous Na₂SO₄ and the solvent was evaporated under reduced pressure. Recrystallization of the obtained residue from a hexane–AcOEt mixture gave single crystals suitable for X-ray analysis.

Yield 15%, m.p. > 438 K (decomp.), pale-beige plates. ¹H NMR (600.2 MHz, CDCl₃) δ 7.79 (d, J = 8.1 Hz, 2H, H-3, H-5 H_arom.), 7.64 (d, J = 8.1 Hz, 2H, H-2, H-6 H_arom.), 4.78 (t, J = 5.0 Hz, 1H, H-6), 4.53 (ddd, J = 4.0 Hz, J = 1.3 Hz, J = 2.3 Hz, 1H, H-5), 4.26 (t, J = 2.3 Hz, 1H, H-4), 4.13 (dd, J = 11.6 Hz, J = 1.7 Hz, 1H), 4.09 (dd, J = 11.6 Hz, J = 1.7 Hz, 1H, H-3), 2.99 (dd, J = 4.5 Hz, J = 9.1 Hz, 1H, H-7a), 2.83 (ddd, J = 1.7 Hz, J = 9.1 Hz, J = 13.1 Hz, 1H, H-7B), 2.35–2.31 (m, 1H, H-7A). ¹³C NMR (150.9 MHz, CDCl₃) δ 172.7, 141.6, 126.7 (q, J = 33.2 Hz, 1C), 126.2 (q, J = 2.9 Hz, 2C), 123.8 (J = 271.6 Hz, 1C), 119.4 (2C), 88.7, 80.1, 55.5, 53.8, 50.5, 49.7, 30.9. ¹⁹F NMR (564.7 MHz, CDCl₃) δ −62.1. IR (KBr): 1703 (NC=O). MS (ESI): m/z = 456 [M + H⁺]. Analysis calculated for C₁₅H₁₂Br₂F₃NO₂: C 39.59%, H 2.66%, N 3.08%. Found: C 39.55%, H 2.61%, N 3.20%.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 4. All C-bound H atoms were placed at calculated positions using a riding model, with aromatic C—H = 0.93–0.98 Å, and with U_iso(H) = 1.2U_eq(C). The F atoms of the trifluoromethyl groups (CF₃) of both molecules are disordered over two sets of sites with refined site occupancies of 0.60 (3)/0.40 (3) for molecule A and 0.640 (15)/0.360 (15) for molecule B. The major and minor components of the disordered CF₃ groups of molecules A and B were restrained to have approximately equal C—F distances by use of the SHELXL SADI instruction. The anisotropies of the F1, F2, F3, F1A, F2A, F3A, F21, F22, F23, F21A, F22A and F23A atoms were restrained with ISOR 0.01 0.02 in SHELXL (Sheldrick, 2015b ). Six outliers ( $[\overline{3}]$ 1 4, $[\overline{1}]$ 2 11, $[\overline{3}]$ 2 5, $[\overline{2}]$ 7 7, $[\overline{1}]$ 4 7 and $[\overline{1}]$ 10 25) were omitted in the final refinement.

Table 4
Experimental details

Crystal data
Chemical formula	C₁₅H₁₂Br₂F₃NO₂
M_r	455.08
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	6.6543 (2), 18.9031 (5), 25.1995 (7)
β (°)	97.132 (2)
V (Å³)	3145.24 (15)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	5.19
Crystal size (mm)	0.44 × 0.12 × 0.04

Data collection
Diffractometer	Bruker KAPPA APEXII area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )
T_min, T_max	0.704, 0.819
No. of measured, independent and observed [I > 2σ(I)] reflections	44884, 7199, 4255
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.077, 1.00
No. of reflections	7199
No. of parameters	471
No. of restraints	204
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.44
Computer programs: APEX2 and SAINT (Bruker, 2013), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2036842

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989021003200/zn2006sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989021003200/zn2006Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989021003200/zn2006Isup3.cml

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); software used to prepare material for publication: PLATON (Spek, 2020).

(3aS,4R,5R,6S,7aR)-4,5-Dibromo-2-[4-(trifluoromethyl)phenyl]-2,3,3a,4,5,6,7,7a-octahydro-3a,6-epoxy-1H-isoindol-1-one top

Crystal data top

C₁₅H₁₂Br₂F₃NO₂	F(000) = 1776
M_r = 455.08	D_x = 1.922 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.6543 (2) Å	Cell parameters from 6983 reflections
b = 18.9031 (5) Å	θ = 3.1–22.1°
c = 25.1995 (7) Å	µ = 5.19 mm⁻¹
β = 97.132 (2)°	T = 296 K
V = 3145.24 (15) Å³	Plate, light beige
Z = 8	0.44 × 0.12 × 0.04 mm

Data collection top

Bruker KAPPA APEXII area-detector diffractometer	4255 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.057
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θ_max = 27.5°, θ_min = 4.2°
T_min = 0.704, T_max = 0.819	h = −8→8
44884 measured reflections	k = −24→24
7199 independent reflections	l = −32→32

Refinement top

Refinement on F²	204 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.0254P)² + 2.067P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
7199 reflections	Δρ_max = 0.52 e Å⁻³
471 parameters	Δρ_min = −0.44 e Å⁻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	Occ. (<1)
Br1	0.04969 (6)	0.49524 (2)	0.40882 (2)	0.05936 (12)
Br2	0.16433 (6)	0.33168 (2)	0.52432 (2)	0.05972 (13)
F1	0.8250 (14)	0.4392 (8)	0.1004 (3)	0.100 (3)	0.60 (3)
F2	0.984 (3)	0.5243 (3)	0.1380 (4)	0.097 (3)	0.60 (3)
F3	1.1221 (17)	0.4233 (8)	0.1395 (5)	0.105 (4)	0.60 (3)
F1A	0.8229 (18)	0.4756 (13)	0.1027 (6)	0.099 (5)	0.40 (3)
F2A	1.084 (3)	0.5104 (9)	0.1523 (7)	0.100 (5)	0.40 (3)
F3A	1.056 (3)	0.4043 (6)	0.1284 (6)	0.082 (4)	0.40 (3)
O1	0.7970 (4)	0.29869 (13)	0.36728 (11)	0.0602 (7)
O8	0.5397 (3)	0.44953 (12)	0.44391 (9)	0.0477 (6)
N2	0.6066 (4)	0.39552 (14)	0.33412 (11)	0.0394 (7)
C1	0.6561 (5)	0.33992 (18)	0.36860 (14)	0.0423 (8)
C3	0.4324 (5)	0.43625 (18)	0.34806 (13)	0.0417 (8)
H3A	0.311584	0.426135	0.323570	0.050*
H3B	0.459315	0.486670	0.347699	0.050*
C3A	0.4104 (5)	0.41102 (17)	0.40351 (13)	0.0368 (8)
C4	0.2098 (5)	0.41007 (17)	0.42722 (13)	0.0394 (8)
H4A	0.131785	0.367487	0.416059	0.047*
C5	0.2862 (5)	0.40741 (18)	0.48724 (13)	0.0436 (8)
H5A	0.254387	0.452572	0.503380	0.052*
C6	0.5167 (5)	0.4022 (2)	0.48785 (14)	0.0489 (9)
H6A	0.592991	0.417081	0.521802	0.059*
C7	0.5857 (5)	0.3323 (2)	0.46770 (15)	0.0548 (10)
H7A	0.526303	0.292812	0.484771	0.066*
H7B	0.732082	0.328072	0.473085	0.066*
C7A	0.5045 (5)	0.33729 (17)	0.40819 (13)	0.0387 (8)
H7AA	0.402046	0.300829	0.398258	0.046*
C11	0.6955 (5)	0.41029 (17)	0.28750 (14)	0.0399 (8)
C12	0.5936 (6)	0.4528 (2)	0.24827 (16)	0.0553 (10)
H12A	0.468838	0.472055	0.253387	0.066*
C13	0.6754 (6)	0.4671 (2)	0.20159 (16)	0.0613 (11)
H13A	0.604994	0.495703	0.175597	0.074*
C14	0.8598 (6)	0.43931 (19)	0.19327 (15)	0.0498 (9)
C15	0.9620 (5)	0.39722 (19)	0.23196 (15)	0.0486 (9)
H15A	1.087012	0.378300	0.226660	0.058*
C16	0.8817 (5)	0.38265 (18)	0.27862 (14)	0.0468 (9)
H16A	0.952961	0.353997	0.304433	0.056*
C17	0.9517 (7)	0.4566 (2)	0.14398 (18)	0.0672 (12)
Br21	−0.02652 (5)	0.90131 (2)	0.77414 (2)	0.05796 (12)
Br22	0.19224 (7)	0.74494 (2)	0.89213 (2)	0.07068 (14)
F21	0.6437 (15)	0.8625 (7)	0.4491 (3)	0.138 (4)	0.640 (15)
F22	0.7980 (19)	0.9531 (3)	0.4818 (4)	0.113 (3)	0.640 (15)
F23	0.9516 (12)	0.8560 (6)	0.4812 (3)	0.116 (3)	0.640 (15)
F21A	0.674 (3)	0.9420 (7)	0.4653 (6)	0.111 (5)	0.360 (15)
F22A	0.9709 (17)	0.9064 (12)	0.4937 (5)	0.137 (6)	0.360 (15)
F23A	0.751 (3)	0.8377 (5)	0.4539 (4)	0.094 (4)	0.360 (15)
O21	0.7477 (4)	0.73028 (14)	0.72019 (11)	0.0656 (8)
O28	0.4682 (3)	0.87970 (12)	0.79846 (9)	0.0481 (6)
N22	0.5250 (4)	0.81952 (15)	0.69035 (11)	0.0414 (7)
C21	0.6025 (5)	0.76761 (19)	0.72515 (15)	0.0451 (9)
C23	0.3412 (5)	0.85182 (19)	0.70647 (13)	0.0422 (8)
H23A	0.220656	0.833540	0.685316	0.051*
H23B	0.344086	0.902874	0.702787	0.051*
C23A	0.3480 (4)	0.83071 (17)	0.76374 (13)	0.0372 (8)
C24	0.1603 (5)	0.82315 (18)	0.79201 (14)	0.0425 (8)
H24A	0.093727	0.777509	0.783839	0.051*
C25	0.2563 (5)	0.82648 (19)	0.85095 (14)	0.0481 (9)
H25A	0.207680	0.869136	0.867414	0.058*
C26	0.4823 (5)	0.8359 (2)	0.84539 (15)	0.0538 (10)
H26A	0.558598	0.858168	0.876756	0.065*
C27	0.5823 (5)	0.7695 (2)	0.82783 (15)	0.0578 (11)
H27A	0.555775	0.729042	0.849561	0.069*
H27B	0.727365	0.775539	0.828410	0.069*
C27A	0.4739 (5)	0.76308 (18)	0.77028 (14)	0.0431 (8)
H27C	0.386791	0.721131	0.766510	0.052*
C31	0.5911 (5)	0.83652 (18)	0.64070 (14)	0.0418 (8)
C32	0.4639 (6)	0.8728 (2)	0.60261 (15)	0.0556 (10)
H32A	0.336348	0.886497	0.610202	0.067*
C33	0.5228 (7)	0.8889 (2)	0.55368 (17)	0.0674 (12)
H33A	0.435143	0.913322	0.528468	0.081*
C34	0.7117 (7)	0.8691 (2)	0.54186 (17)	0.0624 (11)
C35	0.8395 (6)	0.8327 (2)	0.57932 (17)	0.0597 (11)
H35A	0.966193	0.818608	0.571272	0.072*
C36	0.7822 (5)	0.81668 (19)	0.62877 (16)	0.0508 (9)
H36A	0.870853	0.792753	0.654043	0.061*
C37	0.7765 (9)	0.8866 (3)	0.4889 (2)	0.0852 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0517 (2)	0.0598 (3)	0.0702 (3)	0.01235 (19)	0.0221 (2)	0.0094 (2)
Br2	0.0562 (2)	0.0703 (3)	0.0529 (3)	−0.0180 (2)	0.00743 (19)	0.0129 (2)
F1	0.139 (5)	0.110 (7)	0.053 (4)	−0.014 (4)	0.028 (3)	0.003 (4)
F2	0.146 (7)	0.066 (4)	0.090 (5)	−0.004 (4)	0.059 (5)	0.013 (3)
F3	0.098 (5)	0.135 (7)	0.095 (6)	0.033 (5)	0.060 (4)	0.032 (5)
F1A	0.106 (6)	0.124 (9)	0.073 (6)	0.007 (6)	0.033 (5)	0.039 (6)
F2A	0.111 (8)	0.104 (8)	0.093 (7)	−0.056 (6)	0.048 (6)	−0.011 (5)
F3A	0.123 (8)	0.063 (5)	0.075 (6)	0.000 (5)	0.065 (6)	−0.016 (4)
O1	0.0612 (16)	0.0520 (16)	0.0717 (19)	0.0192 (13)	0.0251 (14)	0.0135 (14)
O8	0.0473 (14)	0.0514 (15)	0.0459 (15)	−0.0230 (11)	0.0111 (11)	−0.0137 (12)
N2	0.0396 (15)	0.0386 (16)	0.0414 (17)	0.0037 (13)	0.0107 (13)	−0.0023 (14)
C1	0.0430 (19)	0.038 (2)	0.046 (2)	−0.0013 (16)	0.0085 (17)	−0.0035 (17)
C3	0.0440 (19)	0.038 (2)	0.045 (2)	0.0012 (15)	0.0123 (16)	−0.0014 (16)
C3A	0.0372 (17)	0.038 (2)	0.0360 (19)	−0.0049 (15)	0.0076 (15)	−0.0069 (15)
C4	0.0397 (18)	0.0359 (19)	0.043 (2)	−0.0047 (15)	0.0074 (16)	−0.0032 (16)
C5	0.047 (2)	0.044 (2)	0.041 (2)	−0.0137 (16)	0.0122 (16)	−0.0071 (17)
C6	0.043 (2)	0.069 (3)	0.034 (2)	−0.0185 (19)	−0.0001 (16)	−0.0061 (19)
C7	0.042 (2)	0.071 (3)	0.051 (2)	0.0065 (19)	0.0047 (18)	0.010 (2)
C7A	0.0369 (18)	0.0373 (19)	0.042 (2)	−0.0022 (15)	0.0069 (15)	−0.0033 (16)
C11	0.0433 (19)	0.0356 (19)	0.042 (2)	−0.0004 (16)	0.0106 (16)	−0.0053 (16)
C12	0.056 (2)	0.054 (2)	0.060 (3)	0.0161 (19)	0.023 (2)	0.010 (2)
C13	0.073 (3)	0.058 (3)	0.056 (3)	0.022 (2)	0.021 (2)	0.014 (2)
C14	0.062 (2)	0.042 (2)	0.049 (2)	0.0024 (18)	0.022 (2)	−0.0051 (18)
C15	0.046 (2)	0.054 (2)	0.049 (2)	0.0034 (18)	0.0199 (18)	−0.0035 (19)
C16	0.048 (2)	0.046 (2)	0.046 (2)	0.0053 (17)	0.0057 (17)	−0.0022 (18)
C17	0.085 (3)	0.061 (3)	0.060 (3)	0.011 (3)	0.029 (3)	−0.001 (3)
Br21	0.0449 (2)	0.0658 (3)	0.0640 (3)	0.01529 (19)	0.01001 (18)	−0.0037 (2)
Br22	0.0775 (3)	0.0783 (3)	0.0609 (3)	0.0063 (2)	0.0271 (2)	0.0142 (2)
F21	0.152 (6)	0.201 (8)	0.066 (4)	−0.033 (5)	0.033 (4)	−0.014 (5)
F22	0.168 (7)	0.079 (4)	0.105 (5)	−0.015 (4)	0.070 (5)	0.016 (3)
F23	0.133 (5)	0.135 (6)	0.098 (4)	0.027 (4)	0.084 (4)	0.020 (4)
F21A	0.140 (9)	0.106 (8)	0.096 (7)	0.033 (6)	0.058 (6)	0.041 (6)
F22A	0.127 (8)	0.169 (11)	0.126 (8)	−0.033 (7)	0.058 (6)	0.029 (7)
F23A	0.155 (9)	0.073 (6)	0.060 (5)	0.006 (6)	0.044 (6)	−0.004 (4)
O21	0.0596 (16)	0.0704 (19)	0.071 (2)	0.0285 (14)	0.0227 (14)	0.0036 (15)
O28	0.0453 (13)	0.0506 (15)	0.0469 (15)	−0.0105 (11)	−0.0005 (11)	−0.0058 (12)
N22	0.0339 (14)	0.0492 (18)	0.0421 (17)	0.0020 (13)	0.0088 (13)	−0.0051 (14)
C21	0.0384 (19)	0.047 (2)	0.050 (2)	0.0017 (17)	0.0064 (17)	−0.0056 (18)
C23	0.0351 (17)	0.049 (2)	0.043 (2)	0.0041 (15)	0.0061 (15)	−0.0030 (17)
C23A	0.0323 (16)	0.0379 (19)	0.041 (2)	−0.0039 (15)	0.0022 (15)	−0.0074 (16)
C24	0.0396 (18)	0.042 (2)	0.047 (2)	0.0026 (15)	0.0097 (16)	−0.0066 (17)
C25	0.054 (2)	0.050 (2)	0.043 (2)	0.0045 (18)	0.0140 (17)	−0.0065 (18)
C26	0.051 (2)	0.068 (3)	0.040 (2)	−0.005 (2)	−0.0041 (18)	−0.006 (2)
C27	0.042 (2)	0.079 (3)	0.052 (3)	0.013 (2)	0.0056 (18)	0.009 (2)
C27A	0.0360 (18)	0.042 (2)	0.052 (2)	0.0030 (15)	0.0069 (16)	0.0021 (17)
C31	0.0422 (19)	0.044 (2)	0.040 (2)	−0.0074 (16)	0.0101 (16)	−0.0095 (17)
C32	0.053 (2)	0.066 (3)	0.050 (3)	0.009 (2)	0.015 (2)	0.001 (2)
C33	0.076 (3)	0.069 (3)	0.059 (3)	0.005 (2)	0.019 (2)	0.007 (2)
C34	0.081 (3)	0.055 (3)	0.056 (3)	−0.015 (2)	0.028 (2)	−0.010 (2)
C35	0.057 (2)	0.059 (3)	0.068 (3)	−0.012 (2)	0.028 (2)	−0.017 (2)
C36	0.042 (2)	0.057 (2)	0.055 (2)	−0.0074 (17)	0.0092 (18)	−0.0097 (19)
C37	0.113 (5)	0.080 (4)	0.069 (4)	−0.019 (4)	0.038 (3)	−0.003 (3)

Geometric parameters (Å, º) top

Br1—C4	1.954 (3)	Br21—C24	1.947 (3)
Br2—C5	1.941 (3)	Br22—C25	1.935 (4)
F1—F1A	0.691 (15)	F21—F23A	0.852 (11)
F1—C17	1.341 (7)	F21—C37	1.332 (7)
F1—F3A	1.738 (15)	F21—F21A	1.564 (13)
F2—F2A	0.764 (14)	F22—F21A	0.899 (13)
F2—C17	1.308 (7)	F22—C37	1.280 (7)
F2—F1A	1.596 (14)	F22—F22A	1.452 (14)
F3—F3A	0.610 (16)	F23—F22A	1.007 (15)
F3—C17	1.314 (7)	F23—C37	1.337 (7)
F3—F2A	1.703 (13)	F23—F23A	1.463 (13)
F1A—C17	1.313 (9)	F21A—C37	1.347 (9)
F2A—C17	1.345 (9)	F22A—C37	1.338 (9)
F3A—C17	1.295 (9)	F23A—C37	1.275 (9)
O1—C1	1.223 (4)	O21—C21	1.215 (4)
O8—C3A	1.446 (4)	O28—C26	1.437 (4)
O8—C6	1.446 (4)	O28—C23A	1.445 (4)
N2—C1	1.377 (4)	N22—C21	1.373 (4)
N2—C11	1.407 (4)	N22—C31	1.414 (4)
N2—C3	1.470 (4)	N22—C23	1.469 (4)
C1—C7A	1.505 (4)	C21—C27A	1.508 (5)
C3—C3A	1.501 (4)	C23—C23A	1.492 (5)
C3—H3A	0.9700	C23—H23A	0.9700
C3—H3B	0.9700	C23—H23B	0.9700
C3A—C7A	1.527 (4)	C23A—C24	1.520 (4)
C3A—C4	1.529 (4)	C23A—C27A	1.526 (4)
C4—C5	1.535 (5)	C24—C25	1.543 (5)
C4—H4A	0.9800	C24—H24A	0.9800
C5—C6	1.536 (5)	C25—C26	1.538 (5)
C5—H5A	0.9800	C25—H25A	0.9800
C6—C7	1.508 (5)	C26—C27	1.511 (5)
C6—H6A	0.9800	C26—H26A	0.9800
C7—C7A	1.532 (5)	C27—C27A	1.542 (5)
C7—H7A	0.9700	C27—H27A	0.9700
C7—H7B	0.9700	C27—H27B	0.9700
C7A—H7AA	0.9800	C27A—H27C	0.9800
C11—C12	1.385 (5)	C31—C32	1.380 (5)
C11—C16	1.388 (4)	C31—C36	1.394 (5)
C12—C13	1.382 (5)	C32—C33	1.374 (5)
C12—H12A	0.9300	C32—H32A	0.9300
C13—C14	1.375 (5)	C33—C34	1.379 (6)
C13—H13A	0.9300	C33—H33A	0.9300
C14—C15	1.372 (5)	C34—C35	1.374 (6)
C14—C17	1.488 (5)	C34—C37	1.489 (6)
C15—C16	1.379 (5)	C35—C36	1.381 (5)
C15—H15A	0.9300	C35—H35A	0.9300
C16—H16A	0.9300	C36—H36A	0.9300

F1A—F1—C17	72.7 (11)	F23A—F21—C37	67.4 (8)
F1A—F1—F3A	111.7 (13)	F23A—F21—F21A	114.4 (10)
C17—F1—F3A	47.6 (5)	C37—F21—F21A	54.7 (5)
F2A—F2—C17	76.0 (9)	F21A—F22—C37	74.0 (8)
F2A—F2—F1A	123.5 (11)	F21A—F22—F22A	127.7 (11)
C17—F2—F1A	52.6 (4)	C37—F22—F22A	58.3 (5)
F3A—F3—C17	74.8 (13)	F22A—F23—C37	68.0 (7)
F3A—F3—F2A	122.7 (14)	F22A—F23—F23A	116.4 (9)
C17—F3—F2A	51.0 (4)	C37—F23—F23A	54.0 (4)
F1—F1A—C17	77.2 (11)	F22—F21A—C37	66.0 (7)
F1—F1A—F2	127.1 (13)	F22—F21A—F21	115.1 (10)
C17—F1A—F2	52.4 (5)	C37—F21A—F21	53.8 (5)
F2—F2A—C17	70.6 (9)	F23—F22A—C37	67.8 (7)
F2—F2A—F3	112.5 (12)	F23—F22A—F22	116.3 (9)
C17—F2A—F3	49.4 (4)	C37—F22A—F22	54.5 (5)
F3—F3A—C17	78.2 (12)	F21—F23A—C37	74.6 (8)
F3—F3A—F1	121.1 (15)	F21—F23A—F23	129.5 (10)
C17—F3A—F1	49.9 (5)	C37—F23A—F23	58.0 (5)
C3A—O8—C6	96.7 (2)	C26—O28—C23A	96.0 (2)
C1—N2—C11	125.8 (3)	C21—N22—C31	126.4 (3)
C1—N2—C3	112.5 (3)	C21—N22—C23	112.3 (3)
C11—N2—C3	121.4 (3)	C31—N22—C23	120.8 (3)
O1—C1—N2	126.4 (3)	O21—C21—N22	126.1 (3)
O1—C1—C7A	125.2 (3)	O21—C21—C27A	125.3 (3)
N2—C1—C7A	108.4 (3)	N22—C21—C27A	108.6 (3)
N2—C3—C3A	103.1 (3)	N22—C23—C23A	103.3 (3)
N2—C3—H3A	111.1	N22—C23—H23A	111.1
C3A—C3—H3A	111.1	C23A—C23—H23A	111.1
N2—C3—H3B	111.1	N22—C23—H23B	111.1
C3A—C3—H3B	111.1	C23A—C23—H23B	111.1
H3A—C3—H3B	109.1	H23A—C23—H23B	109.1
O8—C3A—C3	112.2 (3)	O28—C23A—C23	111.2 (3)
O8—C3A—C7A	101.7 (2)	O28—C23A—C24	101.6 (3)
C3—C3A—C7A	106.0 (3)	C23—C23A—C24	123.4 (3)
O8—C3A—C4	101.7 (2)	O28—C23A—C27A	102.5 (2)
C3—C3A—C4	124.0 (3)	C23—C23A—C27A	106.2 (3)
C7A—C3A—C4	109.2 (3)	C24—C23A—C27A	110.0 (3)
C3A—C4—C5	100.8 (2)	C23A—C24—C25	100.4 (3)
C3A—C4—Br1	112.0 (2)	C23A—C24—Br21	111.0 (2)
C5—C4—Br1	111.4 (2)	C25—C24—Br21	111.6 (2)
C3A—C4—H4A	110.8	C23A—C24—H24A	111.1
C5—C4—H4A	110.8	C25—C24—H24A	111.1
Br1—C4—H4A	110.8	Br21—C24—H24A	111.1
C4—C5—C6	102.7 (3)	C26—C25—C24	102.1 (3)
C4—C5—Br2	113.0 (2)	C26—C25—Br22	115.1 (3)
C6—C5—Br2	115.1 (2)	C24—C25—Br22	113.0 (2)
C4—C5—H5A	108.6	C26—C25—H25A	108.8
C6—C5—H5A	108.6	C24—C25—H25A	108.8
Br2—C5—H5A	108.6	Br22—C25—H25A	108.8
O8—C6—C7	102.6 (3)	O28—C26—C27	102.9 (3)
O8—C6—C5	98.8 (3)	O28—C26—C25	100.2 (3)
C7—C6—C5	113.5 (3)	C27—C26—C25	113.7 (3)
O8—C6—H6A	113.5	O28—C26—H26A	113.0
C7—C6—H6A	113.5	C27—C26—H26A	113.0
C5—C6—H6A	113.5	C25—C26—H26A	113.0
C6—C7—C7A	101.0 (3)	C26—C27—C27A	99.7 (3)
C6—C7—H7A	111.6	C26—C27—H27A	111.8
C7A—C7—H7A	111.6	C27A—C27—H27A	111.8
C6—C7—H7B	111.6	C26—C27—H27B	111.8
C7A—C7—H7B	111.6	C27A—C27—H27B	111.8
H7A—C7—H7B	109.4	H27A—C27—H27B	109.5
C1—C7A—C3A	102.8 (3)	C21—C27A—C23A	103.1 (3)
C1—C7A—C7	117.8 (3)	C21—C27A—C27	117.5 (3)
C3A—C7A—C7	102.9 (3)	C23A—C27A—C27	102.8 (3)
C1—C7A—H7AA	110.9	C21—C27A—H27C	110.9
C3A—C7A—H7AA	110.9	C23A—C27A—H27C	110.9
C7—C7A—H7AA	110.9	C27—C27A—H27C	110.9
C12—C11—C16	118.1 (3)	C32—C31—C36	118.7 (3)
C12—C11—N2	119.5 (3)	C32—C31—N22	119.8 (3)
C16—C11—N2	122.4 (3)	C36—C31—N22	121.5 (3)
C13—C12—C11	120.8 (3)	C33—C32—C31	121.0 (4)
C13—C12—H12A	119.6	C33—C32—H32A	119.5
C11—C12—H12A	119.6	C31—C32—H32A	119.5
C14—C13—C12	120.6 (4)	C32—C33—C34	120.2 (4)
C14—C13—H13A	119.7	C32—C33—H33A	119.9
C12—C13—H13A	119.7	C34—C33—H33A	119.9
C15—C14—C13	119.1 (3)	C35—C34—C33	119.4 (4)
C15—C14—C17	120.2 (3)	C35—C34—C37	120.2 (4)
C13—C14—C17	120.7 (4)	C33—C34—C37	120.4 (5)
C14—C15—C16	120.8 (3)	C34—C35—C36	120.8 (4)
C14—C15—H15A	119.6	C34—C35—H35A	119.6
C16—C15—H15A	119.6	C36—C35—H35A	119.6
C15—C16—C11	120.7 (3)	C35—C36—C31	119.8 (4)
C15—C16—H16A	119.6	C35—C36—H36A	120.1
C11—C16—H16A	119.6	C31—C36—H36A	120.1
F3A—C17—F2	127.6 (8)	F23A—C37—F22	128.3 (7)
F3A—C17—F1A	106.8 (9)	F22—C37—F21	107.7 (7)
F2—C17—F1A	75.0 (7)	F23A—C37—F23	68.1 (6)
F2—C17—F3	107.6 (6)	F22—C37—F23	106.8 (6)
F1A—C17—F3	123.2 (9)	F21—C37—F23	104.5 (6)
F3A—C17—F1	82.5 (8)	F23A—C37—F22A	107.8 (8)
F2—C17—F1	103.9 (6)	F22—C37—F22A	67.3 (7)
F3—C17—F1	105.9 (6)	F21—C37—F22A	134.9 (8)
F3A—C17—F2A	105.1 (7)	F23A—C37—F21A	104.0 (8)
F1A—C17—F2A	105.5 (7)	F21—C37—F21A	71.4 (7)
F3—C17—F2A	79.7 (7)	F23—C37—F21A	132.3 (7)
F1—C17—F2A	130.3 (8)	F22A—C37—F21A	104.6 (8)
F3A—C17—C14	112.0 (7)	F23A—C37—C34	115.6 (6)
F2—C17—C14	113.7 (5)	F22—C37—C34	113.3 (5)
F1A—C17—C14	115.2 (7)	F21—C37—C34	111.1 (5)
F3—C17—C14	114.5 (6)	F23—C37—C34	112.9 (5)
F1—C17—C14	110.4 (5)	F22A—C37—C34	111.6 (7)
F2A—C17—C14	111.5 (7)	F21A—C37—C34	112.5 (7)

F3A—F1—F1A—C17	−27.9 (13)	F22A—F22—F21A—C37	24.2 (13)
C17—F1—F1A—F2	16.9 (19)	C37—F22—F21A—F21	−22.7 (10)
F3A—F1—F1A—F2	−11 (3)	F22A—F22—F21A—F21	1 (2)
F2A—F2—F1A—F1	8 (4)	F23A—F21—F21A—F22	−7 (2)
C17—F2—F1A—F1	−21 (2)	C37—F21—F21A—F22	25.9 (12)
F2A—F2—F1A—C17	29.2 (19)	F23A—F21—F21A—C37	−33.1 (13)
F1A—F2—F2A—C17	−23.6 (14)	F23A—F23—F22A—C37	24.6 (9)
C17—F2—F2A—F3	26.8 (11)	C37—F23—F22A—F22	−25.6 (9)
F1A—F2—F2A—F3	3 (2)	F23A—F23—F22A—F22	−1.0 (16)
F3A—F3—F2A—F2	−11 (4)	F21A—F22—F22A—F23	2 (2)
C17—F3—F2A—F2	−34.1 (15)	C37—F22—F22A—F23	29.5 (10)
F3A—F3—F2A—C17	23 (3)	F21A—F22—F22A—C37	−27.6 (16)
F2A—F3—F3A—C17	−18 (2)	F21A—F21—F23A—C37	28.9 (11)
C17—F3—F3A—F1	26.6 (18)	C37—F21—F23A—F23	−19.7 (14)
F2A—F3—F3A—F1	8 (4)	F21A—F21—F23A—F23	9 (2)
F1A—F1—F3A—F3	2 (4)	F22A—F23—F23A—F21	−6 (2)
C17—F1—F3A—F3	−35 (3)	C37—F23—F23A—F21	22.6 (16)
F1A—F1—F3A—C17	37 (2)	F22A—F23—F23A—C37	−28.5 (11)
C11—N2—C1—O1	7.5 (6)	C31—N22—C21—O21	4.1 (6)
C3—N2—C1—O1	−178.0 (3)	C23—N22—C21—O21	176.5 (3)
C11—N2—C1—C7A	−171.5 (3)	C31—N22—C21—C27A	−174.4 (3)
C3—N2—C1—C7A	3.0 (4)	C23—N22—C21—C27A	−2.1 (4)
C1—N2—C3—C3A	13.8 (4)	C21—N22—C23—C23A	17.2 (4)
C11—N2—C3—C3A	−171.4 (3)	C31—N22—C23—C23A	−169.9 (3)
C6—O8—C3A—C3	−167.2 (3)	C26—O28—C23A—C23	−166.9 (3)
C6—O8—C3A—C7A	−54.4 (3)	C26—O28—C23A—C24	60.0 (3)
C6—O8—C3A—C4	58.3 (3)	C26—O28—C23A—C27A	−53.8 (3)
N2—C3—C3A—O8	85.4 (3)	N22—C23—C23A—O28	85.8 (3)
N2—C3—C3A—C7A	−24.7 (3)	N22—C23—C23A—C24	−153.2 (3)
N2—C3—C3A—C4	−152.0 (3)	N22—C23—C23A—C27A	−25.0 (3)
O8—C3A—C4—C5	−32.6 (3)	O28—C23A—C24—C25	−36.2 (3)
C3—C3A—C4—C5	−159.7 (3)	C23—C23A—C24—C25	−161.6 (3)
C7A—C3A—C4—C5	74.4 (3)	C27A—C23A—C24—C25	71.8 (3)
O8—C3A—C4—Br1	85.9 (3)	O28—C23A—C24—Br21	81.9 (3)
C3—C3A—C4—Br1	−41.2 (4)	C23—C23A—C24—Br21	−43.5 (4)
C7A—C3A—C4—Br1	−167.1 (2)	C27A—C23A—C24—Br21	−170.0 (2)
C3A—C4—C5—C6	−3.6 (3)	C23A—C24—C25—C26	0.4 (3)
Br1—C4—C5—C6	−122.6 (2)	Br21—C24—C25—C26	−117.3 (3)
C3A—C4—C5—Br2	−128.3 (2)	C23A—C24—C25—Br22	−123.9 (2)
Br1—C4—C5—Br2	112.7 (2)	Br21—C24—C25—Br22	118.5 (2)
C3A—O8—C6—C7	57.2 (3)	C23A—O28—C26—C27	58.8 (3)
C3A—O8—C6—C5	−59.4 (3)	C23A—O28—C26—C25	−58.6 (3)
C4—C5—C6—O8	38.5 (3)	C24—C25—C26—O28	35.6 (3)
Br2—C5—C6—O8	161.8 (2)	Br22—C25—C26—O28	158.5 (2)
C4—C5—C6—C7	−69.5 (4)	C24—C25—C26—C27	−73.4 (4)
Br2—C5—C6—C7	53.8 (4)	Br22—C25—C26—C27	49.4 (4)
O8—C6—C7—C7A	−36.4 (3)	O28—C26—C27—C27A	−39.5 (3)
C5—C6—C7—C7A	69.2 (3)	C25—C26—C27—C27A	67.9 (4)
O1—C1—C7A—C3A	162.7 (3)	O21—C21—C27A—C23A	167.8 (3)
N2—C1—C7A—C3A	−18.2 (3)	N22—C21—C27A—C23A	−13.6 (4)
O1—C1—C7A—C7	50.5 (5)	O21—C21—C27A—C27	55.6 (5)
N2—C1—C7A—C7	−130.5 (3)	N22—C21—C27A—C27	−125.8 (3)
O8—C3A—C7A—C1	−91.0 (3)	O28—C23A—C27A—C21	−92.9 (3)
C3—C3A—C7A—C1	26.4 (3)	C23—C23A—C27A—C21	23.9 (3)
C4—C3A—C7A—C1	162.1 (3)	C24—C23A—C27A—C21	159.6 (3)
O8—C3A—C7A—C7	31.9 (3)	O28—C23A—C27A—C27	29.7 (3)
C3—C3A—C7A—C7	149.3 (3)	C23—C23A—C27A—C27	146.5 (3)
C4—C3A—C7A—C7	−75.0 (3)	C24—C23A—C27A—C27	−77.8 (3)
C6—C7—C7A—C1	114.7 (3)	C26—C27—C27A—C21	117.8 (3)
C6—C7—C7A—C3A	2.5 (3)	C26—C27—C27A—C23A	5.4 (3)
C1—N2—C11—C12	160.0 (3)	C21—N22—C31—C32	159.3 (3)
C3—N2—C11—C12	−14.1 (5)	C23—N22—C31—C32	−12.5 (5)
C1—N2—C11—C16	−18.8 (5)	C21—N22—C31—C36	−19.9 (5)
C3—N2—C11—C16	167.1 (3)	C23—N22—C31—C36	168.3 (3)
C16—C11—C12—C13	0.2 (6)	C36—C31—C32—C33	0.3 (6)
N2—C11—C12—C13	−178.7 (3)	N22—C31—C32—C33	−178.9 (4)
C11—C12—C13—C14	−0.1 (6)	C31—C32—C33—C34	−0.1 (6)
C12—C13—C14—C15	0.0 (6)	C32—C33—C34—C35	0.4 (6)
C12—C13—C14—C17	−177.8 (4)	C32—C33—C34—C37	−179.8 (4)
C13—C14—C15—C16	0.1 (6)	C33—C34—C35—C36	−0.9 (6)
C17—C14—C15—C16	177.8 (4)	C37—C34—C35—C36	179.3 (4)
C14—C15—C16—C11	0.0 (5)	C34—C35—C36—C31	1.1 (6)
C12—C11—C16—C15	−0.1 (5)	C32—C31—C36—C35	−0.8 (5)
N2—C11—C16—C15	178.7 (3)	N22—C31—C36—C35	178.3 (3)
F3—F3A—C17—F2	48 (3)	F21—F23A—C37—F22	−67.6 (15)
F1—F3A—C17—F2	−101.8 (9)	F23—F23A—C37—F22	94.5 (9)
F3—F3A—C17—F1A	132 (2)	F23—F23A—C37—F21	162.1 (13)
F1—F3A—C17—F1A	−18.0 (9)	F21—F23A—C37—F23	−162.1 (13)
F1—F3A—C17—F3	−150 (2)	F21—F23A—C37—F22A	−142.4 (11)
F3—F3A—C17—F1	150 (2)	F23—F23A—C37—F22A	19.7 (8)
F3—F3A—C17—F2A	20 (2)	F21—F23A—C37—F21A	−31.8 (13)
F1—F3A—C17—F2A	−129.8 (8)	F23—F23A—C37—F21A	130.3 (7)
F3—F3A—C17—C14	−101 (2)	F21—F23A—C37—C34	92.0 (12)
F1—F3A—C17—C14	109.0 (6)	F23—F23A—C37—C34	−105.8 (6)
F2A—F2—C17—F3A	−55.3 (17)	F21A—F22—C37—F23A	62.3 (14)
F1A—F2—C17—F3A	99.9 (10)	F22A—F22—C37—F23A	−95.3 (10)
F2A—F2—C17—F1A	−155.2 (17)	F21A—F22—C37—F21	25.5 (12)
F2A—F2—C17—F3	−34.5 (16)	F22A—F22—C37—F21	−132.0 (8)
F1A—F2—C17—F3	120.7 (9)	F21A—F22—C37—F23	137.3 (11)
F2A—F2—C17—F1	−146.5 (14)	F22A—F22—C37—F23	−20.3 (8)
F1A—F2—C17—F1	8.7 (10)	F21A—F22—C37—F22A	157.6 (13)
F1A—F2—C17—F2A	155.2 (17)	F22A—F22—C37—F21A	−157.6 (13)
F2A—F2—C17—C14	93.5 (15)	F21A—F22—C37—C34	−97.7 (12)
F1A—F2—C17—C14	−111.3 (8)	F22A—F22—C37—C34	104.7 (8)
F1—F1A—C17—F3A	38 (2)	F21A—F21—C37—F23A	−147.4 (13)
F2—F1A—C17—F3A	−125.4 (8)	F23A—F21—C37—F22	130.4 (12)
F1—F1A—C17—F2	163 (2)	F21A—F21—C37—F22	−17.0 (8)
F1—F1A—C17—F3	61 (2)	F23A—F21—C37—F23	17.1 (12)
F2—F1A—C17—F3	−101.5 (8)	F21A—F21—C37—F23	−130.3 (7)
F2—F1A—C17—F1	−163 (2)	F23A—F21—C37—F22A	55.1 (16)
F1—F1A—C17—F2A	149.1 (17)	F21A—F21—C37—F22A	−92.3 (11)
F2—F1A—C17—F2A	−13.9 (9)	F23A—F21—C37—F21A	147.4 (13)
F1—F1A—C17—C14	−87.5 (19)	F23A—F21—C37—C34	−105.0 (12)
F2—F1A—C17—C14	109.5 (6)	F21A—F21—C37—C34	107.6 (7)
F2A—F3—C17—F3A	160 (2)	F22A—F23—C37—F23A	152.5 (11)
F3A—F3—C17—F2	−142 (2)	F22A—F23—C37—F22	27.3 (10)
F2A—F3—C17—F2	18.5 (9)	F23A—F23—C37—F22	−125.3 (8)
F3A—F3—C17—F1A	−58 (2)	F22A—F23—C37—F21	141.3 (10)
F2A—F3—C17—F1A	101.8 (9)	F23A—F23—C37—F21	−11.3 (8)
F3A—F3—C17—F1	−31 (2)	F23A—F23—C37—F22A	−152.5 (11)
F2A—F3—C17—F1	129.1 (8)	F22A—F23—C37—F21A	63.3 (13)
F3A—F3—C17—F2A	−160 (2)	F23A—F23—C37—F21A	−89.2 (12)
F3A—F3—C17—C14	91 (2)	F22A—F23—C37—C34	−97.9 (10)
F2A—F3—C17—C14	−109.0 (7)	F23A—F23—C37—C34	109.6 (7)
F1A—F1—C17—F3A	−144 (2)	F23—F22A—C37—F23A	−26.7 (11)
F1A—F1—C17—F2	−17 (2)	F22—F22A—C37—F23A	124.9 (8)
F3A—F1—C17—F2	127.0 (8)	F23—F22A—C37—F22	−151.6 (10)
F3A—F1—C17—F1A	144 (2)	F23—F22A—C37—F21	−58.8 (13)
F1A—F1—C17—F3	−130.2 (19)	F22—F22A—C37—F21	92.8 (11)
F3A—F1—C17—F3	13.7 (10)	F22—F22A—C37—F23	151.6 (10)
F1A—F1—C17—F2A	−40 (2)	F23—F22A—C37—F21A	−136.9 (9)
F3A—F1—C17—F2A	103.5 (10)	F22—F22A—C37—F21A	14.6 (9)
F1A—F1—C17—C14	105.3 (18)	F23—F22A—C37—C34	101.2 (9)
F3A—F1—C17—C14	−110.7 (7)	F22—F22A—C37—C34	−107.2 (6)
F2—F2A—C17—F3A	137.6 (14)	F22—F21A—C37—F23A	−134.3 (11)
F3—F2A—C17—F3A	−9.1 (11)	F21—F21A—C37—F23A	20.0 (8)
F3—F2A—C17—F2	−146.7 (15)	F21—F21A—C37—F22	154.3 (12)
F2—F2A—C17—F1A	24.9 (17)	F22—F21A—C37—F21	−154.3 (12)
F3—F2A—C17—F1A	−121.8 (9)	F22—F21A—C37—F23	−61.4 (14)
F2—F2A—C17—F3	146.7 (15)	F21—F21A—C37—F23	92.9 (10)
F2—F2A—C17—F1	44.6 (17)	F22—F21A—C37—F22A	−21.3 (13)
F3—F2A—C17—F1	−102.1 (9)	F21—F21A—C37—F22A	133.0 (8)
F2—F2A—C17—C14	−100.8 (14)	F22—F21A—C37—C34	99.9 (10)
F3—F2A—C17—C14	112.4 (7)	F21—F21A—C37—C34	−105.8 (6)
C15—C14—C17—F3A	35.6 (11)	C35—C34—C37—F23A	83.5 (11)
C13—C14—C17—F3A	−146.7 (10)	C33—C34—C37—F23A	−96.2 (11)
C15—C14—C17—F2	−118.1 (9)	C35—C34—C37—F22	−113.7 (8)
C13—C14—C17—F2	59.6 (10)	C33—C34—C37—F22	66.5 (9)
C15—C14—C17—F1A	157.9 (13)	C35—C34—C37—F21	124.9 (8)
C13—C14—C17—F1A	−24.4 (14)	C33—C34—C37—F21	−54.9 (9)
C15—C14—C17—F3	6.2 (11)	C35—C34—C37—F23	7.9 (8)
C13—C14—C17—F3	−176.1 (10)	C33—C34—C37—F23	−171.9 (7)
C15—C14—C17—F1	125.6 (8)	C35—C34—C37—F22A	−40.1 (13)
C13—C14—C17—F1	−56.8 (9)	C33—C34—C37—F22A	140.1 (12)
C15—C14—C17—F2A	−81.9 (13)	C35—C34—C37—F21A	−157.2 (11)
C13—C14—C17—F2A	95.8 (13)	C33—C34—C37—F21A	23.0 (12)

Hydrogen-bond geometry (Å, º) top

Cg5 and Cg10 are the centroids of the C11–C16 and C31–C36 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O8ⁱ	0.98	2.57	3.342 (4)	135
C7—H7A···Br2	0.97	2.82	3.300 (4)	112
C16—H16A···O1	0.93	2.26	2.853 (4)	121
C27—H27A···Br22	0.97	2.78	3.259 (4)	111
C36—H36A···O21	0.93	2.28	2.856 (5)	120
C7A—H7AA···Cg10ⁱ	0.98	2.94	3.741 (4)	139
C27A—H27C···Cg5ⁱ	0.98	2.97	3.924 (4)	166

Symmetry code: (i) −x+1, −y+1, −z+1.

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

Asterisks indicate please define.

Contact	Distance	Symmetry operation
H5A···O8	2.57	1 - x, 1 - y, 1 - z
H3B···O28	2.82	x, 3/2 - y, - 1/2 + z
H4A···O1	2.74	-1 + x, y, z
Br2···Br22	3.74	-x, -1/2 + y, 3/2 - z
Br2···H26A	2.95	1 - x, -1/2 + y, 3/2 - z
H7AA···C36	2.59	1 - x, 1 - y, 1 - z
F3A···F23	2.90	2 - x, -1/2 + y, 1/2 - z
H15A···O21	2.62	2 - x, 1 - y, 1 - z
*F2A···H23B	2.60	1 + x, 3/2 - y, -1/2 + z
H23A···H36A	2.49	-1 + x, y, z
H23B···*F2A	2.60	-1 + x, 3/2 - y, 1/2 + z
Br22···*F23	3.48	-1 + x, 3/2 - y, 1/2 + z
F22A···F1	2.94	2 - x, 1/2 + y, 1/2 - z
H33A···*F21A	2.84	1 - x, 2 - y, 1 - z
F22A···F22	3.09	2 - x, 2 - y, 1 - z

Percentage contributions of interatomic contacts to the Hirshfeld surface for the molecules A and B of the title compound top

Contact	Molecule A	Molecule B
H···H	23.8	22.4
Br···H/H···Br	18.3	12.3
O···H/H···O	14.3	9.7
F···H/H···F	10.4	19.1
C···H/H···C	9.9	7.8
F···F	6.9	8.6
Br···F/F···Br	3.9	8.0
Br···C/C···Br	3.7	3.5
Br···Br	2.4	1.6
F···C/C···F	2.3	2.4
Br···O/O···Br	1.4	2.1
Br···N/N···Br	1.1	0.9
O···N/N···O	0.5	0.5
O···C/C···O	0.5	0.4
C···C	0.3	0.3
N···H/H···N	0.2	0.3
N···C/C···N	0.1	0.1

Funding information

Funding for this research was provided by the Ministry of Education and Science of the Russian Federation [Award No. 075–03-2020–223 (FSSF-2020–0017)].

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