Properties and interactions – melting point of tri­bromo­benzene isomers

Bujak, M.; Podsiadło, M.; Katrusiak, A.

doi:10.1107/S2052520621006399

research papers

STRUCTURAL SCIENCE
CRYSTAL ENGINEERING
MATERIALS

ISSN: 2052-5206

Volume 77| Part 4| August 2021| Pages 632-637

https://doi.org/10.1107/S2052520621006399

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Properties and interactions – melting point of tribromobenzene isomers

Maciej Bujak,^a ^* Marcin Podsiadło ^b and Andrzej Katrusiak ^b ^*

^aFaculty of Chemistry, University of Opole, Oleska 48, Opole, 45-052, Poland, and ^bFaculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, Poznań, 61-614, Poland
^*Correspondence e-mail: mbujak@uni.opole.pl, katran@amu.edu.pl

Edited by J. Lipkowski, Polish Academy of Sciences, Poland (Received 1 April 2021; accepted 19 June 2021; online 24 July 2021)

Single crystals of isomeric 1,2,3-tribromobenzene (123TBB), 1,2,4-tribromobenzene (124TBB) and 1,3,5-tribromobenzene (135TBB) have been grown from different solvents and their structures determined by X-ray diffraction at 100, 200 and 270 K. The melting-point differences of ca 40 K between 135TBB, 123TBB and 124TBB have been correlated with the molecular symmetry and packing preferences in the crystal, as well as with the main types of intermolecular halogen interactions, i.e. Br⋯Br, Br⋯C (Br⋯π) and Br⋯H. The relationship between symmetry and melting point in Carnelley's rule has been extended to the accessibility of terminal atoms for the formation of intermolecular interactions, their occurrences and distribution, and the close packing. The electrostatic potential mapped on molecular surfaces demonstrates that in more symmetric molecules the more evenly distributed substituents are more accessible and form more optimum intermolecular interactions.

Keywords: tribromobenzene isomers; structure-property relationship; melting point; molecular symmetry; noncovalent interactions; halogen bond.

CCDC references: 2041515; 2041516; 2041517; 2041518; 2041519; 2041520; 2041521; 2041522; 2041523

1. Introduction

Melting point is one of the fundamental thermodynamic parameters that can be quickly and cheaply determined, and used, along with other parameters, to identify a substance, check its purity and characterize its properties. Most physicochemical tables list melting and boiling points, and solubility, along with other parameters of various compounds. These parameters change in a characteristic way for compounds forming a homologous series, for example, analogous derivatives with different substituents. However, the most interesting from a structural point of view are the exceptions and anomalies in the well established trends of these series, and in particular polymorphs and very similar compounds, including isomers.

Numerous studies have been dedicated to the rules and factors affecting the melting point that could be calculated as the quotient of enthalpy and entropy of melting (Carnelley, 1882 ; Beacall, 1928 ; Holler, 1948 ; Gavezzotti, 1995 ; Brown & Brown, 2000 ; Boese et al., 1999 ; Thalladi & Boese, 2000 ; Thalladi et al., 2000a ,b ,c ; Katritzky et al., 2001 ; Bujak et al., 2008 ; Joseph et al., 2011 ; Podsiadło et al., 2012 , 2013 ; Yalkowsky & Alantary, 2018 ; Gallagher et al., 2019 ). The studies showed that the location of substituents in molecules and their ability to form intermolecular interactions cannot be neglected when explaining the melting-point differences of isomers. In a recent study on tetrachlorobenzene isomers, both the nature and distribution of interactions were correlated with the melting points of these relatively simple compounds, by representing the molecular symmetry and magnitudes of electrostatic potential on the molecular surfaces (Bujak, 2018 ).

In this article, we continue our studies on the differences in melting points of isomers for tribromobenzenes (Scheme 1 shows the tribromobenzene isomers, their abbreviations, the molecular point-group symmetries and the melting points). We have determined the crystal structures at 270, 200 and 100 K. The experimental study is supported by a Hirshfeld surface analysis and quantum-chemical calculations. We were particularly interested in the nature of the intermolecular interactions, their thermal behaviour and the relationships of the various structural parameters to the differences in the melting points of these compounds.

All tribromobenzene isomers are solid under ambient conditions, with their melting points above 315 K (Mackay et al., 2006 ). As illustrated in Fig. 1, in accordance with the molecular symmetry and Carnelley's rule (Carnelley, 1882; Brown & Brown, 2000), the highest melting point is that of 135TBB (396.0 K, molecular symmetry D_3h), then lower by 35 K is that of 123TBB (361.0 K C_2v symmetry) and still 43 K lower is that of 124TBB (317.7 K, C_s symmetry). These melting-point differences indicate that the structural dissimilarities between the tribromobenzene isomers could be related to their molecular symmetry (i.e. the location of the Br atoms in the aromatic ring), as well as the distinct molecular interactions and crystal packing preferences.

Figure 1
Melting points (Mackay et al., 2006

) for series of isomers: (•) trichloro- (TCB), (♦) tribromo- (TBB) and (▴) triiodobenzenes (TIB), plotted as a function of their molecular weight. The dashed lines joining the points are guides for the eye only.

Of all the tribromobenzenes, so far only the structure of 135TBB was determined at room temperature (Milledge & Pant, 1960 ; Belaaraj et al., 1984 ). Milledge & Pant (1960) established that 135TBB does not undergo any discontinuous phase transition between room and liquid-nitrogen temperature.

2. Experimental

Samples of 123TBB (98%; Tokyo Chemical Industry Co. Ltd), 124TBB and 135TBB (95 and 99%, respectively; Fluorochem Ltd) were recrystallized from different solvents. The best crystals of 123TBB and 124TBB were obtained at room temperature by the slow evaporation from ethanol (96%, POCH S.A.) solutions, whereas for 135TCB, the tetrachloromethane (EUROCHEM BGD Sp. z o.o.) solution performed better.

Single crystals of the tribromobenzene isomers were selected under a polarizing microscope and sealed in thin-walled glass capillaries (from Hilgenberg GmbH, with an internal diameter of 0.3 mm and walls 0.01 mm thick). The samples were cooled in a stream of nitrogen gas from an Oxford Cryosystems attachment. The diffraction data were collected for each crystal first at 270 K and then at 200 K and 100 K on a single-crystal Xcalibur Eos CCD diffractometer with graphite-monochromated Mo Kα radiation. Reflections were measured using the ω-scan technique with Δω = 1.0° images exposed for 10 (for 123TBB and 135TBB) and 7.5 s (for 124TBB). CrysAlisPro (Rigaku Oxford Diffraction, 2018 $[Rigaku Oxford Diffraction (2018). CrysAlisPro. Rigaku Corporation, The Woodlands, TX, USA.]$ ) was used for collecting data and data reduction. All data were accounted for Lorentz, polarization and analytical sample absorption effects. The structures were solved by direct methods and refined with SHELX (Sheldrick, 2008 , 2015 ). Noncentrosymmetric 124TBB and 135TBB were refined as inversion twins. The H-atom positions in all the structures were located in difference Fourier maps and the riding model was applied. The isotropic displacement parameters of the H atoms were fixed to 1.2U_eq of their carriers.

Intermolecular contacts were compared using Hirshfeld surface analysis with CrystalExplorer17 (Turner et al., 2017 ) and the structures were drawn with Mercury (Macrae et al., 2020 ). The geometry optimizations and the calculations for 123TBB, 124TBB and 135TBB were performed using the Gaussian 09 program package (Frisch et al., 2009 ), along with the GaussView 5.0 graphical interface (Dennington et al., 2009 ). Density functional theory (DFT) calculations were carried out at the B3LYP/6-311-G(2d,2p) level of theory (Becke, 1988 ; Lee et al., 1988 ), in a vacuum, for the starting models of the isolated molecules adopted from the X-ray diffraction results.

3. Results

123TBB crystallizes in the monoclinic space group P2₁/c, 124TBB in the orthorhombic space group Fdd2 and 135TBB in the orthorhombic space group P2₁2₁2₁. There is one independent molecule in the asymmetric unit for 135TBB, two for 123TBB and three for 124TBB. For these isomers, no transition or symmetry changes were detected from 270 to 100 K. In this temperature range, the volume of the unit cells of the crystals similarly contract by 3.01 (123TBB), 2.67 (124TBB) and 3.04% (135TBB); their unit-cell parameters contract nearly linearly, but at different rates. The largest linear contraction of 1.49% is that of the shortest a parameter in 135TBB (Table 1 and Tables S1–S3 in the supporting information).

Table 1
Selected crystal data for 123TBB, 124TBB and 135TBB at 100 K

	123TBB	124TBB	135TBB
Chemical formula	C₆H₃Br₃	C₆H₃Br₃	C₆H₃Br₃
M_r	314.78	314.78	314.78
Crystal system	Monoclinic	Orthorhombic	Orthorhombic
Space group, Z, Z′	P2₁/c, 8, 2	Fdd2, 48, 3	P2₁2₁2₁, 4, 1
a (Å)	12.7973 (5)	29.313 (2)	4.00341 (11)
b (Å)	8.2623 (3)	78.645 (4)	13.4119 (3)
c (Å)	15.4666 (6)	3.9320 (2)	14.0916 (4)
β (°)	113.102 (5)	90	90
V (Å³)	1504.22 (11)	9064.5 (9)	756.63 (3)
R[F² > 2σ(F²)]	0.027	0.061	0.018
wR(F²)	0.055	0.135	0.036

The crystals of all the studied isomers, similar to other halogenated benzenes, can be considered as being built of layers composed of tribromobenzene molecules connected through Br⋯Br/C/H interactions (Figs. S1–S3 in the supporting information). At 100 K, the distance between parallel aromatic rings is similar, ca 3.5 Å, in both 123TBB and 135TBB, and it is ca 3.6 Å in 124TBB. The molecules of 123TBB, 124TBB and 135TBB are nearly planar as scrutinized in the supporting information.

The molecular dimensions of the studied tribromobenzenes show some steric hindrance between adjacent Br and H substituents in the aromatic rings. The shortest intramolecular distances of Br⋯Br = 3.307 (1) Å, H⋯H = 2.30 Å and Br⋯H = 2.83 Å, which are clearly below the sums of the van der Waals radii (Bondi, 1964 ), are present in 123TBB and 124TBB at 270 K.

Intermolecular contacts involving Br atoms are present in all isomers and their lengths decrease on cooling (Table 2 and Tables S7, S8 and S10). The largest contraction of −0.081 (5) Å between 270 and 100 K is for the Br11⋯Br34 halogen bond in 124TBB. Also, the Br⋯H contacts, in general, contract on cooling (Tables S8 and S9). Interestingly, according to the criterion of the sum of the van der Waals radii, at 270 K, intermolecular Br⋯Br bonds are present only in 123TBB and 124TBB, whereas the first Br⋯Br halogen bond in 135TBB appears in the structure at ca 175 K (Tables 2 and S10). The intermolecular contacts for the structures of the isomers at 100 K are discussed below.

Table 2
Short intermolecular Br⋯Br distances (Å) and angles (°) in 123TBB, 124TBB and 135TBB at 270, 200 and 100 K

	270 K	200 K	100 K
123TBB
Br11⋯Br12ⁱ	3.6440 (10)	3.6175 (8)	3.5850 (6)
C11—Br11⋯Br12ⁱ	162.75 (19)	162.83 (17)	163.37 (15)
Br11⋯Br12ⁱ—C12ⁱ	135.03 (16)	135.19 (14)	135.10 (12)

124TBB
Br11⋯Br34ⁱⁱ	3.687 (4)	3.651 (3)	3.606 (3)
C11—Br11⋯Br34ⁱⁱ	99.2 (7)	99.4 (6)	99.7 (5)
Br11⋯Br34ⁱⁱ—C34ⁱⁱ	171.2 (7)	172.6 (6)	172.2 (6)
Br14⋯Br21ⁱⁱⁱ	3.751 (4)	3.722 (3)	3.676 (3)
C14—Br14⋯Br21ⁱⁱⁱ	86.3 (6)	86.2 (6)	86.0 (6)
Br14⋯Br21ⁱⁱⁱ—C21ⁱⁱⁱ	161.4 (7)	162.0 (6)	162.1 (6)
Br14⋯Br31	3.698 (4)	3.672 (3)	3.640 (3)
C14—Br14⋯Br31	165.7 (8)	165.2 (7)	165.4 (6)
Br14⋯Br31—C31	105.6 (7)	105.0 (6)	105.5 (6)
Br21⋯Br24^iv	3.630 (4)	3.606 (3)	3.565 (3)
C21—Br21⋯Br24^iv	102.7 (6)	102.3 (6)	103.3 (5)
Br21⋯Br24^iv—C24^iv	174.2 (7)	174.9 (6)	175.9 (6)

135TBB
Br13⋯Br13^v	3.7411 (13)	3.7094 (9)	3.6724 (8)
C13—Br13⋯Br13^v	151.9 (2)	152.15 (16)	152.14 (15)
Br13⋯Br13^v—C13^v	112.4 (2)	112.16 (15)	112.30 (14)
Br13⋯Br15^vi	3.7458 (11)	3.7252 (8)	3.6994 (7)
C13—Br13⋯Br15^vi	118.4 (2)	117.95 (15)	117.93 (15)
Br13⋯Br15^vi—C15^vi	156.1 (2)	155.94 (17)	156.24 (16)
Symmetry codes: (i) −x + 1, y + $[1 \over 2]$ , −z + $[1 \over 2]$ ; (ii) x − $[1 \over 2]$ , y, z + $[3 \over 2]$ ; (iii) x, y, z + 1; (iv) x + $[1 \over 4]$ , −y + $[1 \over 4]$ , z − $[3 \over 4]$ ; (v) x − $[1 \over 2]$ , −y + $[1 \over 2]$ , −z; (vi) −x + $[1 \over 2]$ , −y + 1, z − $[1 \over 2]$ .

In 123TBB, the intermolecular Br11⋯Br12 distance is 3.5850 (6) Å. Atoms Br13 and Br23 are involved in C13—Br13⋯π and C23—Br23⋯π interactions (Pang et al., 2013 ; Wang et al., 2016 ; Mahadevi & Sastry, 2016 ). The shortest Br⋯C separations are Br13⋯C23 of 3.393 (4) Å and Br23⋯C13 of 3.395 (5) Å, whereas the corresponding Br⋯π(centroid) distances are 3.392 (2) and 3.464 (2) Å, respectively (Spek, 2020 ; Tables 2 and S7, and Fig. S4). The intermolecular interactions of the 124TBB molecules are different. According to the criterion of the van der Waals radii, none of the independent molecules form C—Br⋯π interactions, but only Br⋯Br and Br⋯H interactions. Molecule C(11–C16) is involved in six interactions, while molecules C(21–26) and C(31–36) are involved in four halogen bonds each. The shortest Br⋯Br and Br⋯H distances are 3.565 (3) and 2.97 Å, respectively (Tables 2, S8 and S9, and Fig. S5). In 135TBB, the Br13⋯Br15 distance is 3.6994 (7) Å and atom Br13 is also engaged in two Br⋯Br bonds of 3.6724 (8) Å, as well as in one Br13⋯π interaction, characterized by Br⋯C distance of 3.549 (5) Å and a Br⋯π(centroid) distance of 3.786 (2) Å (Spek, 2020; Tables 2 and S10, and Fig. S6).

The contribution of specific types of interactions to the overall cohesion forces in the crystals can be estimated roughly by the number and interatomic distances of the intermolecular contacts for one molecule. According to this criterion, the largest contribution of the Br⋯Br bonds is in 135TBB. In this compound, the Br atoms are more exposed and better accessed compared to 123TBB and 124TBB. At low temperature, due to crystal contraction, the distances become shorter, approximately at the same rate for all isomers.

The Br⋯Br halogen bonds formed in tribromobenzenes are somewhat distorted from idealized types I and II. In both 124TBB and 135TBB, the Br⋯Br interactions, mainly of electrostatic type II, are relatively long. In contrast, the 123TBB crystal structure is governed by relatively short dispersion type I Br⋯Br bonds (Desiraju & Parthasarathy, 1989 ; Pedireddi et al., 1994 ; Awwadi et al., 2006 ; Fourmigué, 2009 ; Mukherjee et al., 2014 ; Cavallo et al., 2016 ).

The Hirshfeld surfaces and corresponding fingerprint plots illustrate the distribution of the types of cohesion forces in tribromobenzenes (Turner et al., 2017; McKinnon et al., 2004 , 2007 ; Spackman & Jayatilaka, 2009 ). This analysis covers a broad range of possible intermolecular contacts, also those longer than the sums of the van der Waals radii. Contacts shorter than the sums of the van der Waals radii, coloured red in Figs. 2 and S7, mainly relate to Br⋯Br, Br⋯C (Br⋯π) and Br⋯H. All the fingerprint plots contain the sharp central red regions representing Br⋯Br and two symmetrically located blue spikes for Br⋯H contacts. The blue regions close to the Br⋯Br red areas are due to Br⋯C (Br⋯π) contacts (Fig. S7c). The plot for molecule C(11–16) of 124TBB has a different distribution of H⋯H contacts (blue area between the Br⋯H spikes; Fig. S7b).

Figure 2
Hirshfeld surfaces (generated separately for symmetry-independent molecules) mapped with d_norm (−0.02 to 0.80) and close molecules within a radius of 4.0 Å, at 100 K, for (a) two 123TBB molecules [C(11–16) left and C(21–26) right]; (b) three 124TBB molecules [C(11–16) upper, C(21–26) middle and C(31–36) bottom] and (c) 135TBB.

4. Discussion

Because in all the TBB isomers the high and low magnitudes of the calculated electrostatic potentials are associated with the Br atoms, one can expect that the electrostatic interactions mainly govern the aggregation of molecules. Fig. 3 shows the contribution of different contacts, assessed according to their portion on the Hirshfeld surfaces. The contacts involving Br atoms, i.e. Br⋯Br, Br⋯C (Br⋯π) and Br⋯H, constitute at least ca 74% of all contacts in the three isomers. It appears from these statistics that the combined contacts of Br⋯Br and Br⋯C (Br⋯π) correlate with the highest melting point of 135TBB; the sum of the Br⋯Br and Br⋯C (Br⋯π) contributions is ca 38 versus ca 31% for both 123TBB and 124TBB. At the same time, the sum of the Br⋯C (Br⋯π) and Br⋯H contacts for 123TBB (ca 66%) is clearly higher than that for the less symmetric isomer 124TBB (ca 55%), having the lowest melting point.

Figure 3
Distribution of contacts, at 100 K, based on their area on the Hirshfeld surfaces for 123TBB, 124TBB and 135TBB (the averaged values for the independent molecules are presented, cf. Fig. S8).

Neither the variances in the contribution of specific types of contacts at different temperatures nor those for independent molecules significantly affect the above-mentioned analysis (Fig. S8). Furthermore, as mentioned previously, the Br⋯Br halogen bonds in both 135TBB and 124TBB are of distorted type II, whereas those in 123TBB are of distorted type I. Also, the shortest Br⋯H bonds, found in 124TBB only, are of both distorted type I and II interactions. This shows that both the nature and distribution of specific cohesion forces may contribute to the differentiation of the melting points of isomeric tribromobenzenes.

The magnitudes of the calculated molecular electrostatic potential are correlated with the preferences of particular atoms to form intermolecular interactions (Cavallo et al., 2016; Fig. S9). The electrostatic potential on the Br atoms in 135TBB is equally distributed, which favours electrostatic type II halogen bonds evenly distributed in space, because Br atoms are easily accessed for intermolecular interactions.

From a thermodynamic point of view, melting is a process that depends on the balance between the enthalpy and entropy of melting. The enthalpy component is associated mainly with molecular size and intermolecular interactions, whereas entropy, related to molecular symmetry and flexibility, affects the arrangement and packing of molecules (Yalkowsky & Alantary, 2018). Therefore, the high symmetry of molecules facilitates their interactions and crystal formation, which results in a lower entropy of melting and in a higher melting point.

The selected structural and thermodynamic parameters for the tribromobenzene isomers are collected in Table 3. The unit-cell volume per molecule (V/Z) and the calculated density parameters are comparable for all the studied isomers. The void volume/Z and the relative volume of voids gradually decreases from 123TBB to 124TBB and are lowest for 135TBB (Figs. S1–S3). It appears that the melting point for tribromobenzenes decreases with an increasing number of molecules in the asymmetric unit (Z′); however, this regularity does not apply to the 124TIB and 124TCB isomers (Fig. 4). It is intriguing that in this series of isomers, the least dense 135TBB has the highest melting point, which is inconsistent with the observation that more dense crystals usually have higher melting points.

Table 3
Comparison of selected structural and thermodynamic parameters for 123TBB, 124TBB and 135TBB at 100 K

	123TBB	124TBB	135TBB
Space group	P2₁/c	Fdd2	P2₁2₁2₁
Z, Z′	8, 2	48, 3	4, 1
V/Z	188.03	188.8	189.16
Density (calculated, g cm⁻³)	2.780	2.768	2.763
Void volume/Z (Å³)	16.2	10.3	7.4
Void volume of V (%)	8.6	5.4	3.9
Molecular symmetry	mm2; C_2v	m; C_s	$[\overline 6]$ m2; D_3h
Boiling point (K)	556*	548	544
Melting point (K)	361.0	317.7	396.0
Enthalpy of melting (kJ mol⁻¹)	Not available	17.9	21.7
Entropy of melting (J K⁻¹ mol⁻¹)	Not available	56**	55**
Notes and references: () Nakada et al.* (1970 ); (*) entropy of melting calculated from the enthalpy of melting (Kuramochi et al., 2004 ; van der Linde et al., 2005 ) and the melting point (Mackay et al.*, 2006).

Figure 4
Melting points for series of isomers: (•) trichloro- (TCB), (♦) tribromo- (TBB) and (▴) triiodobenzenes (TIB), plotted as a function of Z′. The solid lines join the points for isomers containing the same halogen atoms, while the dashed lines are for isomers with the same halogen-atom positions in an aromatic ring. Both the solid and dashed lines are guides for the eye only.

The tribromobenzene isomers are composed of ordered rigid molecules; thus, the differences in their melting points, like those of disubstituted benzenes (Gavezzotti, 1995; Bujak et al., 2007 ; Dziubek & Katrusiak, 2014 ), can be associated with the enthalpy-related components, such as cohesion forces. This further confirms the arguments based on the analysis of the nature and distribution of intermolecular interactions.

5. Conclusions

The crystals of three tribromobenzene isomers have been investigated at low temperature in order to explore the relationships between the intermolecular interactions and melting points of these compounds. Beside the symmetry, described by Carnelley's rule, the intuitive principle for the melting-point differences can be associated with cohesion forces: the stronger and more frequent the interactions between molecules the more energy is required to melt the crystal. The present results show that the strongest halogen bonds alone cannot account for the melting-point differences. Therefore weaker intermolecular interactions have to be considered too. Higher molecular symmetry provides better access to the Br atoms and hence the specific optimum interactions that correlate with the higher melting point of the particular isomer.

Supporting information

CCDC references: 2041515; 2041516; 2041517; 2041518; 2041519; 2041520; 2041521; 2041522; 2041523

Crystal structure: contains datablocks global, 123TBB_270K, 123TBB_200K, 123TBB_100K, 124TBB_270K, 124TBB_200K, 124TBB_100K, 135TBB_270K, 135TBB_200K, 135TBB_100K. DOI: https://doi.org/10.1107/S2052520621006399/lo5092sup1.cif

Structure factors: contains datablock 123TBB_270K. DOI: https://doi.org/10.1107/S2052520621006399/lo5092123TBB_270Ksup2.hkl

Structure factors: contains datablock 123TBB_200K. DOI: https://doi.org/10.1107/S2052520621006399/lo5092123TBB_200Ksup3.hkl

Structure factors: contains datablock 123TBB_100K. DOI: https://doi.org/10.1107/S2052520621006399/lo5092123TBB_100Ksup4.hkl

Structure factors: contains datablock 124TBB_270K. DOI: https://doi.org/10.1107/S2052520621006399/lo5092124TBB_270Ksup5.hkl

Structure factors: contains datablock 124TBB_200K. DOI: https://doi.org/10.1107/S2052520621006399/lo5092124TBB_200Ksup6.hkl

Structure factors: contains datablock 124TBB_100K. DOI: https://doi.org/10.1107/S2052520621006399/lo5092124TBB_100Ksup7.hkl

Structure factors: contains datablock 135TBB_270K. DOI: https://doi.org/10.1107/S2052520621006399/lo5092135TBB_270Ksup8.hkl

Structure factors: contains datablock 135TBB_200K. DOI: https://doi.org/10.1107/S2052520621006399/lo5092135TBB_200Ksup9.hkl

Structure factors: contains datablock 135TBB_100K. DOI: https://doi.org/10.1107/S2052520621006399/lo5092135TBB_100Ksup10.hkl

Additional Tables and Figures. DOI: https://doi.org/10.1107/S2052520621006399/lo5092sup11.pdf

Computing details top

For all structures, data collection: CrysAlis PRO 1.171.39.46 (Rigaku Oxford Diffraction, 2018); cell refinement: CrysAlis PRO 1.171.39.46 (Rigaku Oxford Diffraction, 2018); data reduction: CrysAlis PRO 1.171.39.46 (Rigaku Oxford Diffraction, 2018); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014); molecular graphics: Mercury (Macrae at al., 2020); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2014).

(123TBB_270K) top

Crystal data top

C₆H₃Br₃	F(000) = 1152
M_r = 314.78	D_x = 2.697 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.9832 (8) Å	Cell parameters from 2431 reflections
b = 8.3806 (6) Å	θ = 3.0–23.2°
c = 15.5159 (10) Å	µ = 15.51 mm⁻¹
β = 113.276 (7)°	T = 270 K
V = 1550.8 (2) Å³	Tabular, yellow
Z = 8	0.48 × 0.25 × 0.18 mm

Data collection top

Xcalibur, Eos diffractometer	3041 independent reflections
Radiation source: fine-focus sealed X-ray tube	1880 reflections with I > 2σ(I)
Detector resolution: 16.1544 pixels mm^-1	R_int = 0.086
ω scans	θ_max = 26.0°, θ_min = 2.9°
Absorption correction: analytical CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −16→16
T_min = 0.046, T_max = 0.172	k = −10→10
21557 measured reflections	l = −19→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.075	w = 1/[σ²(F_o²) + (0.0237P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
3041 reflections	Δρ_max = 0.63 e Å⁻³
164 parameters	Δρ_min = −0.69 e Å⁻³
5 restraints	Extinction correction: SHELXL-2014/7 (Sheldrick 2014), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00081 (8)

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
C11	0.4710 (5)	0.2316 (8)	0.0498 (4)	0.0381 (16)
Br11	0.54810 (6)	0.30051 (10)	0.17491 (5)	0.0658 (3)
C12	0.3829 (4)	0.1276 (7)	0.0257 (4)	0.0337 (15)
Br12	0.33212 (5)	0.04958 (9)	0.11642 (4)	0.0540 (2)
C13	0.3297 (5)	0.0798 (7)	−0.0662 (4)	0.0383 (15)
Br13	0.20629 (6)	−0.05844 (10)	−0.10596 (5)	0.0661 (2)
C14	0.3659 (5)	0.1378 (8)	−0.1329 (4)	0.0500 (18)
H14	0.3298	0.1064	−0.1951	0.060*
C15	0.4546 (5)	0.2415 (9)	−0.1078 (4)	0.0532 (19)
H15	0.4785	0.2799	−0.1530	0.064*
C16	0.5083 (5)	0.2889 (8)	−0.0158 (4)	0.0467 (17)
H16	0.5689	0.3586	0.0017	0.056*
C21	0.0722 (5)	0.7264 (8)	0.0415 (4)	0.0415 (16)
Br21	0.11923 (6)	0.79773 (10)	0.16627 (4)	0.0595 (2)
C22	0.1358 (4)	0.6209 (7)	0.0146 (4)	0.0338 (15)
Br22	0.27375 (5)	0.54326 (9)	0.10268 (4)	0.0526 (2)
C23	0.0982 (4)	0.5767 (7)	−0.0783 (4)	0.0366 (15)
Br23	0.18175 (6)	0.43587 (10)	−0.12067 (5)	0.0612 (2)
C24	−0.0004 (5)	0.6347 (8)	−0.1434 (4)	0.0406 (15)
H24	−0.0251	0.6035	−0.2059	0.049*
C25	−0.0627 (5)	0.7400 (8)	−0.1151 (4)	0.0467 (17)
H25	−0.1295	0.7806	−0.1590	0.056*
C26	−0.0271 (5)	0.7852 (8)	−0.0228 (4)	0.0437 (17)
H26	−0.0699	0.8552	−0.0041	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.039 (3)	0.038 (5)	0.031 (3)	0.009 (3)	0.007 (3)	0.003 (3)
Br11	0.0623 (4)	0.0825 (7)	0.0378 (4)	−0.0100 (4)	0.0041 (3)	−0.0081 (4)
C12	0.039 (3)	0.036 (4)	0.028 (3)	0.011 (3)	0.015 (3)	0.008 (3)
Br12	0.0579 (4)	0.0644 (6)	0.0469 (4)	0.0062 (4)	0.0284 (3)	0.0157 (3)
C13	0.046 (3)	0.028 (4)	0.043 (4)	0.003 (3)	0.021 (3)	0.000 (3)
Br13	0.0638 (5)	0.0593 (6)	0.0634 (5)	−0.0181 (4)	0.0125 (4)	−0.0098 (4)
C14	0.060 (4)	0.052 (5)	0.033 (4)	0.014 (4)	0.013 (3)	−0.004 (3)
C15	0.062 (4)	0.056 (6)	0.054 (5)	0.008 (4)	0.036 (4)	0.007 (4)
C16	0.049 (4)	0.041 (5)	0.052 (4)	−0.001 (3)	0.022 (3)	−0.002 (3)
C21	0.048 (4)	0.040 (5)	0.037 (4)	−0.009 (3)	0.017 (3)	0.003 (3)
Br21	0.0697 (5)	0.0728 (7)	0.0392 (4)	−0.0072 (4)	0.0249 (3)	−0.0093 (4)
C22	0.035 (3)	0.032 (4)	0.032 (3)	−0.002 (3)	0.010 (3)	0.007 (3)
Br22	0.0412 (4)	0.0670 (6)	0.0422 (4)	0.0051 (3)	0.0086 (3)	0.0121 (3)
C23	0.040 (3)	0.031 (4)	0.039 (4)	−0.003 (3)	0.017 (3)	0.001 (3)
Br23	0.0712 (5)	0.0607 (6)	0.0548 (5)	0.0138 (4)	0.0282 (4)	−0.0060 (4)
C24	0.049 (4)	0.036 (5)	0.032 (4)	−0.005 (3)	0.011 (3)	0.000 (3)
C25	0.039 (3)	0.048 (5)	0.043 (4)	0.001 (3)	0.005 (3)	0.011 (3)
C26	0.043 (3)	0.045 (5)	0.046 (4)	0.002 (3)	0.020 (3)	0.003 (3)

Geometric parameters (Å, º) top

C11—C12	1.368 (7)	C21—C26	1.373 (7)
C11—C16	1.375 (8)	C21—C22	1.383 (8)
C11—Br11	1.889 (5)	C21—Br21	1.882 (6)
C12—C13	1.376 (7)	C22—C23	1.377 (7)
C12—Br12	1.892 (5)	C22—Br22	1.888 (5)
C13—C14	1.382 (7)	C23—C24	1.369 (7)
C13—Br13	1.873 (6)	C23—Br23	1.888 (6)
C14—C15	1.370 (9)	C24—C25	1.381 (8)
C14—H14	0.9300	C24—H24	0.9300
C15—C16	1.376 (7)	C25—C26	1.372 (8)
C15—H15	0.9300	C25—H25	0.9300
C16—H16	0.9300	C26—H26	0.9300

C12—C11—C16	121.5 (5)	C26—C21—C22	120.8 (5)
C12—C11—Br11	121.4 (4)	C26—C21—Br21	117.6 (5)
C16—C11—Br11	117.1 (5)	C22—C21—Br21	121.6 (4)
C11—C12—C13	119.5 (5)	C23—C22—C21	118.8 (5)
C11—C12—Br12	121.1 (4)	C23—C22—Br22	120.5 (4)
C13—C12—Br12	119.4 (4)	C21—C22—Br22	120.7 (4)
C12—C13—C14	119.5 (6)	C24—C23—C22	121.2 (6)
C12—C13—Br13	122.3 (4)	C24—C23—Br23	117.6 (4)
C14—C13—Br13	118.1 (5)	C22—C23—Br23	121.2 (4)
C15—C14—C13	120.4 (6)	C23—C24—C25	119.1 (6)
C15—C14—H14	119.8	C23—C24—H24	120.4
C13—C14—H14	119.8	C25—C24—H24	120.4
C14—C15—C16	120.2 (6)	C26—C25—C24	120.7 (6)
C14—C15—H15	119.9	C26—C25—H25	119.7
C16—C15—H15	119.9	C24—C25—H25	119.7
C11—C16—C15	118.9 (6)	C25—C26—C21	119.5 (6)
C11—C16—H16	120.5	C25—C26—H26	120.3
C15—C16—H16	120.5	C21—C26—H26	120.3

C16—C11—C12—C13	−0.4 (9)	C26—C21—C22—C23	0.5 (9)
Br11—C11—C12—C13	−179.6 (4)	Br21—C21—C22—C23	−178.2 (4)
C16—C11—C12—Br12	−179.9 (5)	C26—C21—C22—Br22	178.8 (5)
Br11—C11—C12—Br12	0.9 (7)	Br21—C21—C22—Br22	0.1 (7)
C11—C12—C13—C14	−0.2 (9)	C21—C22—C23—C24	−0.3 (9)
Br12—C12—C13—C14	179.4 (5)	Br22—C22—C23—C24	−178.6 (5)
C11—C12—C13—Br13	−178.6 (5)	C21—C22—C23—Br23	179.0 (4)
Br12—C12—C13—Br13	1.0 (7)	Br22—C22—C23—Br23	0.8 (7)
C12—C13—C14—C15	0.4 (9)	C22—C23—C24—C25	0.4 (9)
Br13—C13—C14—C15	178.9 (5)	Br23—C23—C24—C25	−179.0 (5)
C13—C14—C15—C16	−0.1 (10)	C23—C24—C25—C26	−0.6 (9)
C12—C11—C16—C15	0.7 (9)	C24—C25—C26—C21	0.8 (9)
Br11—C11—C16—C15	179.9 (5)	C22—C21—C26—C25	−0.7 (9)
C14—C15—C16—C11	−0.5 (10)	Br21—C21—C26—C25	178.0 (5)

(123TBB_200K) top

Crystal data top

C₆H₃Br₃	F(000) = 1152
M_r = 314.78	D_x = 2.734 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.8999 (7) Å	Cell parameters from 3083 reflections
b = 8.3264 (5) Å	θ = 3.0–28.4°
c = 15.4925 (8) Å	µ = 15.73 mm⁻¹
β = 113.204 (6)°	T = 200 K
V = 1529.44 (16) Å³	Tabular, yellow
Z = 8	0.48 × 0.25 × 0.18 mm

Data collection top

Xcalibur, Eos diffractometer	2990 independent reflections
Radiation source: fine-focus sealed X-ray tube	2138 reflections with I > 2σ(I)
Detector resolution: 16.1544 pixels mm^-1	R_int = 0.072
ω scans	θ_max = 26.0°, θ_min = 2.9°
Absorption correction: analytical CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −15→15
T_min = 0.045, T_max = 0.169	k = −10→10
21168 measured reflections	l = −19→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.068	w = 1/[σ²(F_o²) + (0.025P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2990 reflections	Δρ_max = 0.72 e Å⁻³
164 parameters	Δρ_min = −0.68 e Å⁻³
0 restraints	Extinction correction: SHELXL-2014/7 (Sheldrick 2014), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00095 (9)

Special details top

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

	x	y	z	U_iso*/U_eq
C11	0.4724 (4)	0.2325 (7)	0.0505 (3)	0.0278 (13)
Br11	0.54901 (5)	0.30067 (9)	0.17552 (4)	0.0461 (2)
C12	0.3828 (4)	0.1264 (6)	0.0257 (3)	0.0240 (12)
Br12	0.33158 (4)	0.04745 (8)	0.11625 (4)	0.03727 (17)
C13	0.3299 (4)	0.0787 (7)	−0.0675 (3)	0.0272 (12)
Br13	0.20564 (5)	−0.06077 (8)	−0.10688 (4)	0.04590 (18)
C14	0.3660 (4)	0.1376 (7)	−0.1333 (3)	0.0325 (13)
H14	0.3299	0.1060	−0.1956	0.039*
C15	0.4552 (4)	0.2432 (8)	−0.1082 (4)	0.0380 (15)
H15	0.4790	0.2825	−0.1536	0.046*
C16	0.5096 (4)	0.2910 (7)	−0.0157 (4)	0.0321 (13)
H16	0.5704	0.3614	0.0017	0.039*
C21	0.0714 (4)	0.7263 (7)	0.0422 (3)	0.0290 (13)
Br21	0.11887 (5)	0.79891 (8)	0.16692 (4)	0.04177 (18)
C22	0.1369 (4)	0.6192 (6)	0.0152 (3)	0.0244 (12)
Br22	0.27423 (4)	0.54196 (8)	0.10302 (4)	0.03664 (17)
C23	0.0976 (4)	0.5743 (7)	−0.0787 (3)	0.0263 (12)
Br23	0.18192 (5)	0.43386 (8)	−0.12093 (4)	0.04256 (18)
C24	−0.0018 (4)	0.6338 (7)	−0.1441 (4)	0.0306 (13)
H24	−0.0269	0.6026	−0.2067	0.037*
C25	−0.0640 (4)	0.7410 (8)	−0.1152 (4)	0.0355 (14)
H25	−0.1313	0.7820	−0.1590	0.043*
C26	−0.0276 (4)	0.7872 (7)	−0.0230 (4)	0.0318 (13)
H26	−0.0698	0.8597	−0.0045	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.030 (3)	0.030 (4)	0.021 (3)	0.007 (2)	0.008 (2)	0.001 (2)
Br11	0.0439 (3)	0.0582 (5)	0.0255 (3)	−0.0076 (3)	0.0023 (3)	−0.0058 (3)
C12	0.028 (3)	0.024 (3)	0.022 (3)	0.004 (2)	0.012 (2)	0.006 (2)
Br12	0.0399 (3)	0.0447 (4)	0.0316 (3)	0.0043 (3)	0.0188 (2)	0.0105 (3)
C13	0.031 (3)	0.021 (3)	0.031 (3)	0.001 (2)	0.014 (2)	−0.001 (2)
Br13	0.0448 (3)	0.0421 (5)	0.0429 (4)	−0.0128 (3)	0.0087 (3)	−0.0071 (3)
C14	0.043 (3)	0.033 (4)	0.017 (3)	0.008 (3)	0.007 (2)	0.000 (2)
C15	0.047 (4)	0.041 (4)	0.036 (4)	0.009 (3)	0.027 (3)	0.007 (3)
C16	0.030 (3)	0.031 (4)	0.034 (3)	−0.001 (3)	0.011 (2)	0.005 (2)
C21	0.033 (3)	0.033 (4)	0.023 (3)	−0.008 (3)	0.014 (2)	0.000 (2)
Br21	0.0485 (3)	0.0525 (5)	0.0263 (3)	−0.0049 (3)	0.0168 (3)	−0.0063 (3)
C22	0.023 (3)	0.025 (4)	0.024 (3)	−0.001 (2)	0.007 (2)	0.007 (2)
Br22	0.0287 (3)	0.0474 (4)	0.0285 (3)	0.0030 (3)	0.0056 (2)	0.0078 (3)
C23	0.033 (3)	0.020 (3)	0.029 (3)	−0.003 (2)	0.014 (2)	−0.002 (2)
Br23	0.0489 (4)	0.0432 (5)	0.0373 (4)	0.0099 (3)	0.0189 (3)	−0.0046 (3)
C24	0.033 (3)	0.032 (4)	0.023 (3)	−0.004 (3)	0.007 (2)	−0.001 (2)
C25	0.028 (3)	0.043 (4)	0.027 (3)	−0.001 (3)	0.003 (2)	0.005 (3)
C26	0.032 (3)	0.032 (4)	0.035 (3)	0.000 (3)	0.017 (3)	0.001 (2)

Geometric parameters (Å, º) top

C11—C16	1.382 (7)	C21—C26	1.376 (7)
C11—C12	1.384 (7)	C21—C22	1.400 (7)
C11—Br11	1.882 (5)	C21—Br21	1.883 (5)
C12—C13	1.391 (6)	C22—C23	1.390 (6)
C12—Br12	1.888 (4)	C22—Br22	1.872 (5)
C13—C14	1.367 (7)	C23—C24	1.376 (7)
C13—Br13	1.876 (5)	C23—Br23	1.881 (5)
C14—C15	1.378 (8)	C24—C25	1.387 (7)
C14—H14	0.9300	C24—H24	0.9300
C15—C16	1.382 (7)	C25—C26	1.372 (7)
C15—H15	0.9300	C25—H25	0.9300
C16—H16	0.9300	C26—H26	0.9300

C16—C11—C12	121.1 (5)	C26—C21—C22	120.7 (5)
C16—C11—Br11	117.6 (4)	C26—C21—Br21	117.8 (4)
C12—C11—Br11	121.4 (4)	C22—C21—Br21	121.4 (4)
C11—C12—C13	119.0 (4)	C23—C22—C21	118.0 (4)
C11—C12—Br12	121.0 (4)	C23—C22—Br22	121.2 (4)
C13—C12—Br12	120.0 (4)	C21—C22—Br22	120.7 (4)
C14—C13—C12	120.0 (5)	C24—C23—C22	121.5 (5)
C14—C13—Br13	118.6 (4)	C24—C23—Br23	117.8 (4)
C12—C13—Br13	121.4 (4)	C22—C23—Br23	120.6 (4)
C13—C14—C15	120.7 (5)	C23—C24—C25	119.0 (5)
C13—C14—H14	119.6	C23—C24—H24	120.5
C15—C14—H14	119.6	C25—C24—H24	120.5
C14—C15—C16	120.2 (5)	C26—C25—C24	120.8 (5)
C14—C15—H15	119.9	C26—C25—H25	119.6
C16—C15—H15	119.9	C24—C25—H25	119.6
C11—C16—C15	119.0 (5)	C25—C26—C21	119.9 (5)
C11—C16—H16	120.5	C25—C26—H26	120.0
C15—C16—H16	120.5	C21—C26—H26	120.0

C16—C11—C12—C13	−0.1 (8)	C26—C21—C22—C23	−1.2 (8)
Br11—C11—C12—C13	−179.4 (4)	Br21—C21—C22—C23	−178.4 (4)
C16—C11—C12—Br12	−179.7 (4)	C26—C21—C22—Br22	177.8 (4)
Br11—C11—C12—Br12	1.0 (6)	Br21—C21—C22—Br22	0.7 (6)
C11—C12—C13—C14	−0.5 (8)	C21—C22—C23—C24	0.7 (8)
Br12—C12—C13—C14	179.1 (4)	Br22—C22—C23—C24	−178.3 (4)
C11—C12—C13—Br13	−178.5 (4)	C21—C22—C23—Br23	178.9 (4)
Br12—C12—C13—Br13	1.2 (6)	Br22—C22—C23—Br23	−0.1 (6)
C12—C13—C14—C15	0.5 (8)	C22—C23—C24—C25	0.0 (8)
Br13—C13—C14—C15	178.5 (4)	Br23—C23—C24—C25	−178.3 (4)
C13—C14—C15—C16	0.1 (9)	C23—C24—C25—C26	−0.1 (8)
C12—C11—C16—C15	0.7 (8)	C24—C25—C26—C21	−0.4 (8)
Br11—C11—C16—C15	180.0 (4)	C22—C21—C26—C25	1.1 (8)
C14—C15—C16—C11	−0.7 (8)	Br21—C21—C26—C25	178.3 (4)

(123TBB_100K) top

Crystal data top

C₆H₃Br₃	F(000) = 1152
M_r = 314.78	D_x = 2.780 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.7973 (5) Å	Cell parameters from 4437 reflections
b = 8.2623 (3) Å	θ = 3.0–31.5°
c = 15.4666 (6) Å	µ = 15.99 mm⁻¹
β = 113.102 (5)°	T = 100 K
V = 1504.22 (11) Å³	Tabular, yellow
Z = 8	0.48 × 0.25 × 0.18 mm

Data collection top

Xcalibur, Eos diffractometer	2944 independent reflections
Radiation source: fine-focus sealed X-ray tube	2364 reflections with I > 2σ(I)
Detector resolution: 16.1544 pixels mm^-1	R_int = 0.060
ω scans	θ_max = 26.0°, θ_min = 2.9°
Absorption correction: analytical CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −15→15
T_min = 0.044, T_max = 0.166	k = −10→10
20735 measured reflections	l = −19→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.055	w = 1/[σ²(F_o²) + (0.0199P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2944 reflections	Δρ_max = 0.71 e Å⁻³
164 parameters	Δρ_min = −0.59 e Å⁻³
0 restraints	Extinction correction: SHELXL-2014/7 (Sheldrick 2014), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00053 (6)

Special details top

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

	x	y	z	U_iso*/U_eq
C11	0.4736 (3)	0.2316 (6)	0.0507 (3)	0.0153 (10)
Br11	0.54994 (4)	0.30087 (6)	0.17635 (3)	0.02269 (13)
C12	0.3833 (3)	0.1246 (5)	0.0258 (3)	0.0115 (9)
Br12	0.33085 (3)	0.04471 (6)	0.11605 (3)	0.01838 (12)
C13	0.3302 (3)	0.0789 (6)	−0.0678 (3)	0.0147 (10)
Br13	0.20472 (4)	−0.06360 (6)	−0.10801 (3)	0.02237 (12)
C14	0.3667 (4)	0.1383 (6)	−0.1344 (3)	0.0175 (10)
H14	0.3305	0.1065	−0.1968	0.021*
C15	0.4568 (3)	0.2448 (6)	−0.1088 (3)	0.0175 (10)
H15	0.4808	0.2854	−0.1540	0.021*
C16	0.5113 (4)	0.2911 (6)	−0.0158 (3)	0.0178 (10)
H16	0.5728	0.3616	0.0020	0.021*
C21	0.0709 (3)	0.7280 (6)	0.0420 (3)	0.0152 (10)
Br21	0.11865 (4)	0.80033 (6)	0.16767 (3)	0.02038 (12)
C22	0.1359 (3)	0.6191 (6)	0.0151 (3)	0.0134 (9)
Br22	0.27500 (3)	0.54020 (6)	0.10351 (3)	0.01850 (12)
C23	0.0971 (3)	0.5749 (6)	−0.0788 (3)	0.0138 (9)
Br23	0.18230 (4)	0.43148 (6)	−0.12113 (3)	0.02108 (12)
C24	−0.0025 (3)	0.6345 (6)	−0.1440 (3)	0.0173 (10)
H24	−0.0272	0.6032	−0.2067	0.021*
C25	−0.0665 (3)	0.7426 (6)	−0.1156 (3)	0.0178 (10)
H25	−0.1342	0.7834	−0.1595	0.021*
C26	−0.0299 (3)	0.7893 (6)	−0.0230 (3)	0.0157 (10)
H26	−0.0727	0.8616	−0.0043	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.014 (2)	0.020 (3)	0.010 (2)	0.0040 (19)	0.0030 (17)	0.0003 (17)
Br11	0.0224 (2)	0.0288 (3)	0.0118 (2)	−0.0039 (2)	0.00123 (18)	−0.00248 (19)
C12	0.014 (2)	0.013 (3)	0.010 (2)	0.0057 (18)	0.0065 (17)	0.0044 (16)
Br12	0.0196 (2)	0.0227 (3)	0.0146 (2)	0.00203 (19)	0.00870 (18)	0.00521 (18)
C13	0.013 (2)	0.013 (3)	0.016 (2)	0.0026 (18)	0.0034 (18)	0.0009 (17)
Br13	0.0227 (2)	0.0213 (3)	0.0195 (3)	−0.0062 (2)	0.00440 (19)	−0.00328 (19)
C14	0.026 (2)	0.014 (3)	0.011 (2)	0.007 (2)	0.0048 (19)	0.0001 (17)
C15	0.022 (2)	0.018 (3)	0.016 (2)	0.005 (2)	0.0120 (19)	0.0036 (18)
C16	0.018 (2)	0.015 (3)	0.020 (3)	−0.0003 (19)	0.0072 (19)	0.0027 (18)
C21	0.018 (2)	0.020 (3)	0.007 (2)	−0.0051 (19)	0.0049 (17)	−0.0015 (17)
Br21	0.0237 (2)	0.0261 (3)	0.0117 (2)	−0.0022 (2)	0.00738 (18)	−0.00286 (18)
C22	0.011 (2)	0.012 (3)	0.018 (2)	0.0001 (18)	0.0064 (17)	0.0046 (17)
Br22	0.0150 (2)	0.0244 (3)	0.0134 (2)	0.00150 (19)	0.00263 (17)	0.00364 (18)
C23	0.018 (2)	0.010 (3)	0.015 (2)	−0.0029 (18)	0.0074 (18)	−0.0020 (17)
Br23	0.0242 (2)	0.0221 (3)	0.0173 (2)	0.0051 (2)	0.00858 (19)	−0.00186 (18)
C24	0.016 (2)	0.021 (3)	0.013 (2)	−0.0042 (19)	0.0040 (18)	−0.0025 (18)
C25	0.012 (2)	0.023 (3)	0.014 (2)	−0.0023 (19)	0.0003 (18)	0.0028 (18)
C26	0.016 (2)	0.016 (3)	0.019 (2)	0.0003 (19)	0.0114 (18)	−0.0012 (18)

Geometric parameters (Å, º) top

C11—C12	1.384 (6)	C21—C26	1.384 (6)
C11—C16	1.386 (6)	C21—C22	1.395 (6)
C11—Br11	1.888 (4)	C21—Br21	1.891 (4)
C12—C13	1.388 (6)	C22—C23	1.386 (6)
C12—Br12	1.890 (4)	C22—Br22	1.886 (4)
C13—C14	1.378 (6)	C23—C24	1.370 (6)
C13—Br13	1.889 (4)	C23—Br23	1.893 (4)
C14—C15	1.379 (6)	C24—C25	1.394 (6)
C14—H14	0.9300	C24—H24	0.9300
C15—C16	1.384 (6)	C25—C26	1.375 (6)
C15—H15	0.9300	C25—H25	0.9300
C16—H16	0.9300	C26—H26	0.9300

C12—C11—C16	121.0 (4)	C26—C21—C22	120.9 (4)
C12—C11—Br11	121.2 (3)	C26—C21—Br21	117.7 (3)
C16—C11—Br11	117.8 (3)	C22—C21—Br21	121.4 (3)
C11—C12—C13	118.6 (4)	C23—C22—C21	118.2 (4)
C11—C12—Br12	121.1 (3)	C23—C22—Br22	121.1 (3)
C13—C12—Br12	120.3 (3)	C21—C22—Br22	120.7 (3)
C14—C13—C12	120.8 (4)	C24—C23—C22	121.6 (4)
C14—C13—Br13	118.0 (3)	C24—C23—Br23	117.8 (3)
C12—C13—Br13	121.2 (3)	C22—C23—Br23	120.6 (3)
C13—C14—C15	120.2 (4)	C23—C24—C25	119.3 (4)
C13—C14—H14	119.9	C23—C24—H24	120.3
C15—C14—H14	119.9	C25—C24—H24	120.3
C14—C15—C16	119.9 (4)	C26—C25—C24	120.4 (4)
C14—C15—H15	120.0	C26—C25—H25	119.8
C16—C15—H15	120.0	C24—C25—H25	119.8
C15—C16—C11	119.6 (4)	C25—C26—C21	119.6 (4)
C15—C16—H16	120.2	C25—C26—H26	120.2
C11—C16—H16	120.2	C21—C26—H26	120.2

C16—C11—C12—C13	−0.6 (7)	C26—C21—C22—C23	0.5 (6)
Br11—C11—C12—C13	179.6 (3)	Br21—C21—C22—C23	−178.3 (3)
C16—C11—C12—Br12	−179.5 (3)	C26—C21—C22—Br22	178.5 (3)
Br11—C11—C12—Br12	0.8 (5)	Br21—C21—C22—Br22	−0.3 (5)
C11—C12—C13—C14	0.2 (6)	C21—C22—C23—C24	−0.4 (6)
Br12—C12—C13—C14	179.0 (3)	Br22—C22—C23—C24	−178.4 (3)
C11—C12—C13—Br13	−178.9 (3)	C21—C22—C23—Br23	178.6 (3)
Br12—C12—C13—Br13	0.0 (5)	Br22—C22—C23—Br23	0.6 (5)
C12—C13—C14—C15	−0.1 (7)	C22—C23—C24—C25	0.1 (7)
Br13—C13—C14—C15	178.9 (3)	Br23—C23—C24—C25	−178.9 (3)
C13—C14—C15—C16	0.5 (7)	C23—C24—C25—C26	0.1 (7)
C14—C15—C16—C11	−1.0 (7)	C24—C25—C26—C21	−0.1 (7)
C12—C11—C16—C15	1.0 (7)	C22—C21—C26—C25	−0.2 (7)
Br11—C11—C16—C15	−179.2 (3)	Br21—C21—C26—C25	178.6 (3)

(124TBB_270K) top

Crystal data top

C₆H₃Br₃	D_x = 2.694 Mg m⁻³
M_r = 314.78	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fdd2	Cell parameters from 3398 reflections
a = 29.408 (3) Å	θ = 4.1–20.4°
b = 79.439 (6) Å	µ = 15.50 mm⁻¹
c = 3.9865 (4) Å	T = 270 K
V = 9313.0 (15) Å³	Needle, yellow
Z = 48	0.93 × 0.13 × 0.07 mm
F(000) = 6912

Data collection top

Xcalibur, Eos diffractometer	4476 independent reflections
Radiation source: fine-focus sealed X-ray tube	2161 reflections with I > 2σ(I)
Detector resolution: 16.1544 pixels mm^-1	R_int = 0.139
ω scans	θ_max = 26.0°, θ_min = 2.8°
Absorption correction: analytical CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −36→36
T_min = 0.037, T_max = 0.387	k = −83→97
19561 measured reflections	l = −4→4

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.067	H-atom parameters constrained
wR(F²) = 0.160	w = 1/[σ²(F_o²) + (0.0465P)²] where P = (F_o² + 2F_c²)/3
S = 0.95	(Δ/σ)_max < 0.001
4476 reflections	Δρ_max = 1.33 e Å⁻³
245 parameters	Δρ_min = −0.84 e Å⁻³
73 restraints	Absolute structure: Refined as an inversion twin.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.46 (7)

Special details top

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
Br11	0.07397 (9)	0.00248 (3)	0.8776 (8)	0.0707 (9)
C11	0.1253 (8)	0.0158 (3)	0.842 (6)	0.051 (6)
Br12	0.17867 (10)	−0.01106 (3)	1.0842 (8)	0.0704 (9)
C12	0.1696 (8)	0.0111 (2)	0.932 (6)	0.045 (5)
C13	0.2066 (8)	0.0218 (3)	0.891 (6)	0.058 (7)
H13	0.2359	0.0183	0.9476	0.069*
Br14	0.25041 (10)	0.05130 (3)	0.7031 (8)	0.0765 (10)
C14	0.1986 (8)	0.0374 (2)	0.767 (6)	0.051 (6)
C15	0.1564 (8)	0.0429 (2)	0.653 (6)	0.053 (6)
H15	0.1527	0.0534	0.5546	0.063*
C16	0.1200 (8)	0.0318 (3)	0.693 (6)	0.058 (6)
H16	0.0913	0.0351	0.6201	0.069*
Br21	0.18344 (9)	0.08524 (3)	0.1320 (8)	0.0665 (9)
C21	0.1344 (8)	0.0994 (2)	0.262 (6)	0.042 (5)
Br22	0.07466 (9)	0.07317 (3)	0.0414 (8)	0.0667 (8)
C22	0.0893 (8)	0.0946 (2)	0.214 (6)	0.046 (6)
C23	0.0553 (7)	0.1052 (2)	0.300 (5)	0.041 (5)
H23	0.0253	0.1023	0.2533	0.049*
Br24	0.01752 (9)	0.13485 (3)	0.5834 (7)	0.0630 (8)
C24	0.0653 (8)	0.1204 (2)	0.458 (6)	0.044 (6)
C25	0.1091 (8)	0.1255 (3)	0.502 (6)	0.053 (6)
H25	0.1154	0.1359	0.5972	0.063*
C26	0.1445 (8)	0.1149 (3)	0.402 (6)	0.054 (6)
H26	0.1746	0.1182	0.4301	0.064*
Br31	0.33664 (9)	0.08115 (3)	0.3840 (8)	0.0665 (8)
C31	0.3833 (8)	0.0677 (3)	0.199 (5)	0.045 (5)
Br32	0.44290 (10)	0.09582 (3)	0.2822 (7)	0.0657 (8)
C32	0.4258 (8)	0.0739 (3)	0.156 (6)	0.046 (6)
C33	0.4600 (8)	0.0635 (2)	0.026 (6)	0.050 (6)
H33	0.4895	0.0676	0.0019	0.060*
Br34	0.49606 (9)	0.03322 (3)	−0.2352 (8)	0.0677 (9)
C34	0.4493 (8)	0.0468 (3)	−0.067 (6)	0.048 (6)
C35	0.4069 (8)	0.0407 (3)	−0.015 (7)	0.060 (7)
H35	0.3999	0.0296	−0.0658	0.072*
C36	0.3742 (8)	0.0514 (3)	0.114 (6)	0.057 (7)
H36	0.3448	0.0473	0.1449	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br11	0.0576 (18)	0.0494 (14)	0.105 (3)	−0.0039 (13)	0.0046 (18)	−0.0037 (17)
C11	0.054 (10)	0.040 (10)	0.059 (14)	−0.017 (9)	0.008 (12)	−0.004 (10)
Br12	0.077 (2)	0.0441 (14)	0.090 (2)	0.0067 (14)	0.0037 (19)	0.0182 (16)
C12	0.056 (11)	0.034 (9)	0.045 (13)	0.010 (8)	0.018 (11)	−0.006 (10)
C13	0.047 (12)	0.042 (11)	0.085 (19)	0.007 (9)	−0.015 (15)	0.006 (13)
Br14	0.0665 (19)	0.0523 (15)	0.111 (3)	−0.0057 (14)	0.0124 (19)	0.0044 (17)
C14	0.056 (11)	0.029 (9)	0.067 (15)	0.009 (9)	0.013 (12)	0.000 (10)
C15	0.070 (13)	0.026 (9)	0.061 (14)	0.013 (8)	−0.001 (12)	0.012 (10)
C16	0.067 (12)	0.042 (11)	0.064 (18)	0.012 (9)	−0.007 (14)	−0.005 (11)
Br21	0.0604 (18)	0.0500 (15)	0.089 (2)	0.0088 (13)	0.0155 (16)	0.0072 (16)
C21	0.049 (10)	0.031 (9)	0.045 (13)	0.008 (9)	0.005 (12)	0.019 (9)
Br22	0.076 (2)	0.0438 (14)	0.080 (2)	−0.0028 (13)	0.0024 (18)	−0.0163 (14)
C22	0.049 (12)	0.027 (10)	0.060 (16)	0.000 (8)	0.005 (12)	0.000 (10)
C23	0.043 (11)	0.039 (10)	0.040 (13)	0.001 (8)	−0.009 (11)	0.006 (10)
Br24	0.0634 (18)	0.0500 (14)	0.0756 (19)	0.0044 (13)	0.0061 (17)	−0.0108 (14)
C24	0.047 (10)	0.028 (10)	0.057 (16)	−0.005 (9)	0.006 (12)	0.000 (9)
C25	0.050 (11)	0.039 (10)	0.070 (16)	−0.014 (8)	0.012 (12)	−0.009 (10)
C26	0.038 (10)	0.055 (11)	0.068 (16)	−0.013 (9)	−0.001 (11)	0.004 (11)
Br31	0.0635 (18)	0.0539 (15)	0.082 (2)	0.0077 (14)	0.0120 (17)	0.0003 (15)
C31	0.058 (12)	0.041 (10)	0.037 (14)	−0.003 (10)	0.002 (12)	0.011 (10)
Br32	0.0719 (19)	0.0430 (13)	0.082 (2)	−0.0029 (13)	−0.0029 (16)	−0.0153 (15)
C32	0.048 (13)	0.045 (11)	0.043 (15)	0.002 (8)	−0.015 (12)	−0.012 (11)
C33	0.050 (12)	0.046 (11)	0.055 (16)	−0.003 (9)	−0.009 (12)	−0.012 (12)
Br34	0.0677 (19)	0.0487 (15)	0.087 (2)	0.0129 (14)	−0.0082 (17)	−0.0121 (15)
C34	0.051 (11)	0.048 (11)	0.045 (15)	0.010 (10)	−0.002 (12)	−0.016 (11)
C35	0.048 (13)	0.035 (11)	0.10 (2)	0.006 (8)	−0.020 (14)	0.004 (12)
C36	0.047 (13)	0.045 (11)	0.08 (2)	−0.005 (9)	0.007 (14)	0.011 (13)

Geometric parameters (Å, º) top

Br11—C11	1.85 (2)	C23—H23	0.9300
C11—C12	1.40 (3)	Br24—C24	1.88 (2)
C11—C16	1.41 (3)	C24—C25	1.36 (3)
Br12—C12	1.88 (2)	C25—C26	1.40 (3)
C12—C13	1.39 (3)	C25—H25	0.9300
C13—C14	1.36 (3)	C26—H26	0.9300
C13—H13	0.9300	Br31—C31	1.89 (2)
Br14—C14	1.90 (2)	C31—C32	1.36 (3)
C14—C15	1.39 (3)	C31—C36	1.37 (3)
C15—C16	1.40 (3)	Br32—C32	1.88 (2)
C15—H15	0.9300	C32—C33	1.40 (3)
C16—H16	0.9300	C33—C34	1.41 (3)
Br21—C21	1.90 (2)	C33—H33	0.9300
C21—C26	1.38 (3)	Br34—C34	1.87 (2)
C21—C22	1.39 (3)	C34—C35	1.35 (3)
Br22—C22	1.89 (2)	C35—C36	1.38 (3)
C22—C23	1.35 (3)	C35—H35	0.9300
C23—C24	1.40 (3)	C36—H36	0.9300

C12—C11—C16	117 (2)	C25—C24—C23	121 (2)
C12—C11—Br11	125.9 (17)	C25—C24—Br24	119.4 (16)
C16—C11—Br11	117.2 (18)	C23—C24—Br24	119.5 (17)
C13—C12—C11	122.5 (19)	C24—C25—C26	119 (2)
C13—C12—Br12	119.8 (18)	C24—C25—H25	120.3
C11—C12—Br12	117.6 (17)	C26—C25—H25	120.3
C14—C13—C12	118 (2)	C21—C26—C25	119 (2)
C14—C13—H13	121.2	C21—C26—H26	120.3
C12—C13—H13	121.2	C25—C26—H26	120.3
C13—C14—C15	124 (2)	C32—C31—C36	120 (2)
C13—C14—Br14	116.1 (18)	C32—C31—Br31	120.7 (17)
C15—C14—Br14	119.5 (16)	C36—C31—Br31	119.4 (18)
C14—C15—C16	117 (2)	C31—C32—C33	119 (2)
C14—C15—H15	121.6	C31—C32—Br32	123.5 (18)
C16—C15—H15	121.6	C33—C32—Br32	116.9 (17)
C15—C16—C11	122 (2)	C32—C33—C34	119 (2)
C15—C16—H16	119.0	C32—C33—H33	120.3
C11—C16—H16	119.0	C34—C33—H33	120.3
C26—C21—C22	120 (2)	C35—C34—C33	120 (2)
C26—C21—Br21	118.2 (17)	C35—C34—Br34	121.6 (17)
C22—C21—Br21	121.6 (16)	C33—C34—Br34	118.1 (17)
C23—C22—C21	120.1 (19)	C34—C35—C36	119 (2)
C23—C22—Br22	119.0 (18)	C34—C35—H35	120.7
C21—C22—Br22	120.9 (16)	C36—C35—H35	120.7
C22—C23—C24	120 (2)	C31—C36—C35	122 (2)
C22—C23—H23	120.1	C31—C36—H36	118.8
C24—C23—H23	120.1	C35—C36—H36	118.8

C16—C11—C12—C13	3 (3)	C22—C23—C24—Br24	−178.9 (17)
Br11—C11—C12—C13	178.8 (19)	C23—C24—C25—C26	−3 (3)
C16—C11—C12—Br12	−173.1 (17)	Br24—C24—C25—C26	−178.6 (18)
Br11—C11—C12—Br12	3 (3)	C22—C21—C26—C25	1 (3)
C11—C12—C13—C14	2 (4)	Br21—C21—C26—C25	−179.6 (18)
Br12—C12—C13—C14	177.2 (17)	C24—C25—C26—C21	0 (3)
C12—C13—C14—C15	−5 (4)	C36—C31—C32—C33	0 (3)
C12—C13—C14—Br14	−178.1 (18)	Br31—C31—C32—C33	178.5 (17)
C13—C14—C15—C16	5 (4)	C36—C31—C32—Br32	−177.2 (18)
Br14—C14—C15—C16	177.2 (17)	Br31—C31—C32—Br32	2 (3)
C14—C15—C16—C11	0 (4)	C31—C32—C33—C34	2 (3)
C12—C11—C16—C15	−3 (4)	Br32—C32—C33—C34	179.0 (17)
Br11—C11—C16—C15	−179.9 (19)	C32—C33—C34—C35	−3 (4)
C26—C21—C22—C23	1 (3)	C32—C33—C34—Br34	−179.3 (17)
Br21—C21—C22—C23	−177.9 (17)	C33—C34—C35—C36	3 (4)
C26—C21—C22—Br22	−177.3 (16)	Br34—C34—C35—C36	178.9 (19)
Br21—C21—C22—Br22	4 (3)	C32—C31—C36—C35	0 (4)
C21—C22—C23—C24	−5 (3)	Br31—C31—C36—C35	−178.7 (19)
Br22—C22—C23—C24	173.8 (16)	C34—C35—C36—C31	−2 (4)
C22—C23—C24—C25	6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···Br12ⁱ	0.93	2.96	3.69 (2)	137
C33—H33···Br22ⁱⁱ	0.93	3.14	3.96 (2)	149
C35—H35···Br12ⁱⁱⁱ	0.93	3.07	3.80 (2)	136

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

(124TBB_200K) top

Crystal data top

C₆H₃Br₃	D_x = 2.716 Mg m⁻³
M_r = 314.78	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fdd2	Cell parameters from 4227 reflections
a = 29.383 (2) Å	θ = 3.8–24.2°
b = 79.163 (4) Å	µ = 15.63 mm⁻¹
c = 3.9713 (3) Å	T = 200 K
V = 9237.4 (10) Å³	Needle, yellow
Z = 48	0.93 × 0.13 × 0.07 mm
F(000) = 6912

Data collection top

Xcalibur, Eos diffractometer	4444 independent reflections
Radiation source: fine-focus sealed X-ray tube	2801 reflections with I > 2σ(I)
Detector resolution: 16.1544 pixels mm^-1	R_int = 0.116
ω scans	θ_max = 26.0°, θ_min = 2.8°
Absorption correction: analytical CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −36→36
T_min = 0.040, T_max = 0.388	k = −83→97
19496 measured reflections	l = −4→4

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.062	H-atom parameters constrained
wR(F²) = 0.137	w = 1/[σ²(F_o²) + (0.0368P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
4444 reflections	Δρ_max = 1.75 e Å⁻³
245 parameters	Δρ_min = −0.90 e Å⁻³
85 restraints	Absolute structure: Refined as an inversion twin.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.42 (6)

Special details top

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
Br11	0.07378 (8)	0.00241 (3)	0.8770 (7)	0.0489 (7)
C11	0.1255 (7)	0.0158 (2)	0.836 (6)	0.037 (5)
Br12	0.17889 (8)	−0.01126 (2)	1.0872 (7)	0.0497 (7)
C12	0.1677 (7)	0.0108 (2)	0.931 (4)	0.026 (4)
C13	0.2053 (7)	0.0215 (2)	0.896 (6)	0.042 (5)
H13	0.2341	0.0180	0.9625	0.051*
Br14	0.25112 (8)	0.05143 (3)	0.7025 (7)	0.0526 (7)
C14	0.1988 (8)	0.0375 (2)	0.762 (6)	0.045 (6)
C15	0.1569 (7)	0.0425 (2)	0.652 (6)	0.041 (5)
H15	0.1535	0.0530	0.5488	0.049*
C16	0.1195 (7)	0.0321 (2)	0.692 (5)	0.039 (5)
H16	0.0907	0.0357	0.6257	0.047*
Br21	0.18420 (8)	0.08511 (2)	0.1299 (6)	0.0459 (6)
C21	0.1358 (7)	0.0993 (2)	0.261 (5)	0.032 (4)
Br22	0.07490 (8)	0.07302 (3)	0.0375 (6)	0.0461 (6)
C22	0.0889 (7)	0.0944 (2)	0.218 (5)	0.029 (4)
C23	0.0558 (7)	0.1054 (2)	0.310 (5)	0.031 (4)
H23	0.0256	0.1025	0.2731	0.037*
Br24	0.01798 (8)	0.13502 (3)	0.5871 (6)	0.0437 (6)
C24	0.0655 (7)	0.1207 (2)	0.454 (5)	0.036 (5)
C25	0.1097 (7)	0.1255 (2)	0.500 (5)	0.038 (5)
H25	0.1165	0.1360	0.5949	0.046*
C26	0.1444 (7)	0.1145 (2)	0.403 (5)	0.040 (5)
H26	0.1745	0.1178	0.4359	0.048*
Br31	0.33683 (8)	0.08126 (3)	0.3870 (7)	0.0460 (6)
C31	0.3840 (7)	0.0674 (2)	0.205 (5)	0.032 (5)
Br32	0.44345 (8)	0.09601 (2)	0.2855 (6)	0.0458 (6)
C32	0.4261 (6)	0.0739 (2)	0.166 (5)	0.029 (4)
C33	0.4616 (7)	0.0636 (2)	0.021 (5)	0.040 (5)
H33	0.4907	0.0678	−0.0170	0.049*
Br34	0.49663 (8)	0.03306 (3)	−0.2411 (6)	0.0460 (6)
C34	0.4501 (7)	0.0471 (2)	−0.058 (5)	0.032 (4)
C35	0.4075 (7)	0.0407 (2)	−0.021 (5)	0.037 (5)
H35	0.4007	0.0297	−0.0859	0.045*
C36	0.3746 (7)	0.0511 (2)	0.116 (5)	0.041 (5)
H36	0.3453	0.0470	0.1479	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br11	0.0391 (14)	0.0330 (11)	0.0744 (18)	−0.0030 (10)	0.0067 (14)	−0.0047 (13)
C11	0.036 (9)	0.024 (8)	0.052 (14)	−0.003 (8)	0.007 (11)	−0.007 (9)
Br12	0.0529 (15)	0.0316 (11)	0.0645 (17)	0.0035 (11)	0.0019 (14)	0.0127 (12)
C12	0.039 (10)	0.025 (8)	0.015 (9)	0.006 (7)	0.008 (8)	0.003 (8)
C13	0.042 (10)	0.030 (9)	0.054 (14)	0.002 (8)	−0.001 (12)	0.001 (10)
Br14	0.0436 (14)	0.0359 (12)	0.0783 (19)	−0.0043 (11)	0.0101 (14)	0.0032 (12)
C14	0.039 (10)	0.027 (9)	0.069 (17)	−0.006 (9)	0.007 (12)	−0.001 (10)
C15	0.046 (10)	0.025 (8)	0.053 (11)	0.005 (7)	0.005 (10)	0.008 (8)
C16	0.040 (10)	0.032 (10)	0.046 (15)	0.005 (8)	−0.016 (11)	−0.004 (9)
Br21	0.0412 (14)	0.0337 (11)	0.0628 (16)	0.0065 (10)	0.0098 (13)	0.0042 (12)
C21	0.036 (6)	0.030 (6)	0.031 (7)	−0.003 (5)	0.008 (6)	0.008 (5)
Br22	0.0530 (16)	0.0300 (11)	0.0553 (16)	−0.0030 (11)	0.0023 (13)	−0.0098 (11)
C22	0.042 (10)	0.018 (8)	0.027 (11)	−0.004 (7)	0.008 (9)	0.004 (8)
C23	0.039 (9)	0.023 (8)	0.030 (11)	−0.001 (7)	0.007 (10)	0.007 (8)
Br24	0.0423 (14)	0.0349 (11)	0.0538 (14)	0.0024 (10)	0.0046 (13)	−0.0081 (11)
C24	0.030 (9)	0.026 (9)	0.050 (15)	0.001 (8)	0.003 (10)	−0.001 (9)
C25	0.032 (10)	0.033 (10)	0.050 (15)	−0.010 (8)	0.014 (11)	0.000 (9)
C26	0.029 (8)	0.041 (8)	0.049 (11)	0.005 (7)	−0.020 (8)	0.001 (8)
Br31	0.0424 (14)	0.0361 (11)	0.0596 (16)	0.0047 (11)	0.0087 (13)	0.0011 (12)
C31	0.030 (9)	0.022 (8)	0.044 (13)	0.000 (8)	−0.006 (10)	0.001 (9)
Br32	0.0463 (15)	0.0296 (11)	0.0614 (17)	−0.0025 (10)	−0.0023 (13)	−0.0122 (11)
C32	0.029 (8)	0.021 (7)	0.037 (10)	0.001 (6)	−0.016 (8)	−0.008 (8)
C33	0.039 (11)	0.037 (10)	0.045 (14)	0.001 (8)	0.002 (11)	−0.012 (10)
Br34	0.0436 (14)	0.0353 (11)	0.0592 (16)	0.0087 (11)	−0.0050 (12)	−0.0085 (11)
C34	0.035 (9)	0.022 (8)	0.040 (12)	0.015 (8)	0.000 (9)	0.000 (8)
C35	0.045 (9)	0.020 (8)	0.046 (11)	0.006 (6)	−0.005 (9)	0.011 (8)
C36	0.038 (9)	0.033 (8)	0.051 (11)	−0.014 (7)	0.012 (9)	−0.003 (9)

Geometric parameters (Å, º) top

Br11—C11	1.861 (19)	C23—H23	0.9300
C11—C12	1.36 (3)	Br24—C24	1.875 (19)
C11—C16	1.42 (2)	C24—C25	1.37 (3)
Br12—C12	1.882 (17)	C25—C26	1.40 (2)
C12—C13	1.40 (3)	C25—H25	0.9300
C13—C14	1.39 (2)	C26—H26	0.9300
C13—H13	0.9300	Br31—C31	1.908 (19)
Br14—C14	1.91 (2)	C31—C32	1.35 (2)
C14—C15	1.36 (3)	C31—C36	1.37 (2)
C15—C16	1.38 (3)	Br32—C32	1.885 (17)
C15—H15	0.9300	C32—C33	1.44 (2)
C16—H16	0.9300	C33—C34	1.38 (2)
Br21—C21	1.887 (19)	C33—H33	0.9300
C21—C26	1.35 (2)	Br34—C34	1.910 (18)
C21—C22	1.44 (3)	C34—C35	1.36 (3)
Br22—C22	1.882 (17)	C35—C36	1.38 (3)
C22—C23	1.35 (2)	C35—H35	0.9300
C23—C24	1.37 (2)	C36—H36	0.9300

C12—C11—C16	119.5 (18)	C25—C24—C23	120.1 (19)
C12—C11—Br11	123.7 (15)	C25—C24—Br24	120.0 (15)
C16—C11—Br11	116.8 (15)	C23—C24—Br24	119.9 (15)
C11—C12—C13	121.1 (17)	C24—C25—C26	118.8 (19)
C11—C12—Br12	121.6 (15)	C24—C25—H25	120.6
C13—C12—Br12	117.1 (15)	C26—C25—H25	120.6
C14—C13—C12	118.8 (19)	C21—C26—C25	122.2 (19)
C14—C13—H13	120.6	C21—C26—H26	118.9
C12—C13—H13	120.6	C25—C26—H26	118.9
C15—C14—C13	120.9 (19)	C32—C31—C36	121.0 (19)
C15—C14—Br14	121.2 (16)	C32—C31—Br31	119.5 (14)
C13—C14—Br14	117.7 (16)	C36—C31—Br31	119.4 (15)
C14—C15—C16	120.3 (19)	C31—C32—C33	119.6 (17)
C14—C15—H15	119.8	C31—C32—Br32	124.9 (15)
C16—C15—H15	119.8	C33—C32—Br32	115.5 (14)
C15—C16—C11	119.3 (19)	C34—C33—C32	116.6 (19)
C15—C16—H16	120.4	C34—C33—H33	121.7
C11—C16—H16	120.4	C32—C33—H33	121.7
C26—C21—C22	118.0 (18)	C35—C34—C33	123.7 (18)
C26—C21—Br21	120.3 (15)	C35—C34—Br34	118.7 (14)
C22—C21—Br21	121.7 (14)	C33—C34—Br34	117.5 (15)
C23—C22—C21	118.6 (17)	C34—C35—C36	117.4 (18)
C23—C22—Br22	121.6 (16)	C34—C35—H35	121.3
C21—C22—Br22	119.8 (14)	C36—C35—H35	121.3
C22—C23—C24	122.2 (19)	C31—C36—C35	121.6 (19)
C22—C23—H23	118.9	C31—C36—H36	119.2
C24—C23—H23	118.9	C35—C36—H36	119.2

C16—C11—C12—C13	2 (3)	C22—C23—C24—Br24	−178.1 (15)
Br11—C11—C12—C13	−179.5 (15)	C23—C24—C25—C26	−1 (3)
C16—C11—C12—Br12	−174.5 (15)	Br24—C24—C25—C26	179.3 (16)
Br11—C11—C12—Br12	4 (3)	C22—C21—C26—C25	−1 (3)
C11—C12—C13—C14	0 (3)	Br21—C21—C26—C25	179.3 (17)
Br12—C12—C13—C14	176.0 (16)	C24—C25—C26—C21	1 (3)
C12—C13—C14—C15	−3 (3)	C36—C31—C32—C33	1 (3)
C12—C13—C14—Br14	−177.7 (15)	Br31—C31—C32—C33	−178.5 (15)
C13—C14—C15—C16	4 (4)	C36—C31—C32—Br32	−179.1 (16)
Br14—C14—C15—C16	179.0 (16)	Br31—C31—C32—Br32	1 (3)
C14—C15—C16—C11	−3 (3)	C31—C32—C33—C34	−2 (3)
C12—C11—C16—C15	0 (3)	Br32—C32—C33—C34	177.9 (15)
Br11—C11—C16—C15	−179.1 (16)	C32—C33—C34—C35	3 (3)
C26—C21—C22—C23	2 (3)	C32—C33—C34—Br34	−178.7 (14)
Br21—C21—C22—C23	−178.3 (14)	C33—C34—C35—C36	−3 (3)
C26—C21—C22—Br22	−177.8 (14)	Br34—C34—C35—C36	179.3 (15)
Br21—C21—C22—Br22	2 (2)	C32—C31—C36—C35	−1 (3)
C21—C22—C23—C24	−3 (3)	Br31—C31—C36—C35	179.1 (16)
Br22—C22—C23—C24	177.3 (15)	C34—C35—C36—C31	1 (3)
C22—C23—C24—C25	2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···Br12ⁱ	0.93	3.01	3.71 (2)	133
C33—H33···Br22ⁱⁱ	0.93	3.07	3.92 (2)	152
C35—H35···Br12ⁱⁱⁱ	0.93	3.05	3.78 (2)	137

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

(124TBB_100K) top

Crystal data top

C₆H₃Br₃	D_x = 2.768 Mg m⁻³
M_r = 314.78	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fdd2	Cell parameters from 5134 reflections
a = 29.313 (2) Å	θ = 3.1–27.2°
b = 78.645 (4) Å	µ = 15.92 mm⁻¹
c = 3.9320 (2) Å	T = 100 K
V = 9064.5 (9) Å³	Needle, yellow
Z = 48	0.93 × 0.13 × 0.07 mm
F(000) = 6912

Data collection top

Xcalibur, Eos diffractometer	4368 independent reflections
Radiation source: fine-focus sealed X-ray tube	3365 reflections with I > 2σ(I)
Detector resolution: 16.1544 pixels mm^-1	R_int = 0.103
ω scans	θ_max = 26.0°, θ_min = 2.8°
Absorption correction: analytical CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −36→36
T_min = 0.042, T_max = 0.375	k = −82→97
19208 measured reflections	l = −4→4

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.061	H-atom parameters constrained
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.0425P)²] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
4368 reflections	Δρ_max = 2.18 e Å⁻³
245 parameters	Δρ_min = −1.72 e Å⁻³
121 restraints	Absolute structure: Refined as an inversion twin.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.45 (6)

Special details top

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
Br11	0.07364 (7)	0.00227 (2)	0.8783 (6)	0.0268 (5)
C11	0.1255 (6)	0.0158 (2)	0.830 (5)	0.016 (4)
Br12	0.17899 (7)	−0.01151 (2)	1.0908 (6)	0.0265 (5)
C12	0.1686 (7)	0.0109 (2)	0.929 (5)	0.016 (4)
C13	0.2060 (7)	0.0215 (2)	0.897 (5)	0.023 (4)
H13	0.2349	0.0180	0.9664	0.028*
Br14	0.25167 (7)	0.05160 (2)	0.7012 (6)	0.0271 (5)
C14	0.1992 (7)	0.0375 (2)	0.759 (5)	0.021 (4)
C15	0.1580 (6)	0.0430 (2)	0.655 (5)	0.017 (4)
H15	0.1549	0.0539	0.5646	0.021*
C16	0.1194 (7)	0.0323 (2)	0.683 (5)	0.018 (4)
H16	0.0909	0.0359	0.6084	0.022*
Br21	0.18472 (7)	0.08497 (2)	0.1248 (5)	0.0229 (5)
C21	0.1358 (7)	0.0989 (2)	0.262 (5)	0.017 (4)
Br22	0.07519 (7)	0.07272 (2)	0.0359 (5)	0.0244 (5)
C22	0.0899 (7)	0.0943 (2)	0.215 (5)	0.019 (4)
C23	0.0555 (7)	0.1052 (2)	0.309 (5)	0.018 (4)
H23	0.0252	0.1021	0.2718	0.021*
Br24	0.01803 (7)	0.13522 (2)	0.5908 (5)	0.0225 (5)
C24	0.0652 (6)	0.1205 (2)	0.456 (5)	0.016 (4)
C25	0.1111 (7)	0.1255 (2)	0.503 (5)	0.024 (4)
H25	0.1180	0.1359	0.6024	0.029*
C26	0.1452 (7)	0.1148 (2)	0.399 (5)	0.020 (4)
H26	0.1754	0.1182	0.4215	0.024*
Br31	0.33716 (7)	0.08135 (2)	0.3904 (6)	0.0243 (5)
C31	0.3841 (6)	0.0677 (2)	0.200 (5)	0.016 (4)
Br32	0.44409 (7)	0.09620 (2)	0.2874 (5)	0.0237 (5)
C32	0.4269 (6)	0.0739 (2)	0.158 (5)	0.017 (4)
C33	0.4623 (7)	0.0635 (2)	0.017 (5)	0.026 (5)
H33	0.4916	0.0676	−0.0189	0.031*
Br34	0.49705 (7)	0.03286 (2)	−0.2465 (5)	0.0249 (5)
C34	0.4501 (6)	0.0469 (2)	−0.064 (5)	0.017 (4)
C35	0.4073 (7)	0.0404 (2)	−0.025 (5)	0.020 (4)
H35	0.4005	0.0294	−0.0890	0.024*
C36	0.3736 (7)	0.0512 (2)	0.116 (5)	0.021 (4)
H36	0.3443	0.0472	0.1526	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br11	0.0240 (12)	0.0168 (9)	0.0396 (13)	−0.0016 (8)	0.0057 (11)	−0.0019 (10)
C11	0.018 (7)	0.017 (6)	0.014 (8)	−0.007 (6)	0.007 (7)	−0.006 (6)
Br12	0.0308 (13)	0.0155 (9)	0.0333 (13)	0.0007 (9)	0.0023 (11)	0.0052 (10)
C12	0.021 (6)	0.014 (5)	0.013 (6)	−0.002 (5)	−0.001 (5)	−0.003 (5)
C13	0.015 (8)	0.024 (8)	0.030 (10)	0.001 (6)	−0.006 (9)	0.007 (8)
Br14	0.0236 (12)	0.0198 (10)	0.0380 (13)	−0.0027 (9)	0.0072 (10)	0.0020 (9)
C14	0.017 (7)	0.020 (7)	0.026 (9)	−0.002 (6)	0.010 (8)	0.004 (7)
C15	0.026 (7)	0.008 (6)	0.019 (8)	0.002 (5)	−0.002 (7)	0.002 (6)
C16	0.022 (8)	0.013 (7)	0.019 (9)	0.003 (6)	−0.002 (8)	−0.006 (7)
Br21	0.0230 (12)	0.0162 (9)	0.0295 (12)	0.0021 (8)	0.0049 (10)	0.0020 (9)
C21	0.018 (6)	0.014 (5)	0.018 (6)	−0.001 (5)	0.005 (5)	0.008 (5)
Br22	0.0295 (13)	0.0151 (9)	0.0285 (12)	−0.0015 (8)	0.0010 (10)	−0.0058 (9)
C22	0.023 (9)	0.013 (8)	0.023 (11)	0.000 (6)	−0.003 (9)	0.008 (8)
C23	0.020 (9)	0.020 (8)	0.013 (10)	−0.003 (7)	−0.002 (9)	0.006 (7)
Br24	0.0232 (12)	0.0182 (9)	0.0260 (11)	0.0015 (8)	0.0022 (11)	−0.0047 (9)
C24	0.014 (7)	0.016 (7)	0.018 (9)	0.003 (6)	0.002 (7)	0.008 (6)
C25	0.022 (9)	0.026 (9)	0.023 (12)	−0.004 (7)	0.004 (10)	−0.005 (8)
C26	0.017 (7)	0.021 (7)	0.021 (9)	−0.001 (6)	−0.009 (8)	0.008 (7)
Br31	0.0247 (12)	0.0197 (9)	0.0284 (11)	0.0040 (8)	0.0054 (11)	−0.0001 (9)
C31	0.018 (7)	0.016 (6)	0.015 (9)	0.006 (6)	−0.002 (7)	0.005 (6)
Br32	0.0258 (12)	0.0157 (9)	0.0296 (12)	−0.0003 (8)	−0.0035 (10)	−0.0061 (9)
C32	0.017 (6)	0.021 (6)	0.014 (6)	−0.001 (5)	−0.007 (5)	−0.003 (5)
C33	0.032 (10)	0.017 (8)	0.030 (12)	−0.002 (7)	0.011 (10)	−0.007 (9)
Br34	0.0262 (12)	0.0176 (9)	0.0310 (12)	0.0038 (9)	−0.0015 (10)	−0.0047 (9)
C34	0.019 (6)	0.015 (5)	0.016 (6)	0.004 (5)	0.001 (5)	−0.004 (5)
C35	0.025 (8)	0.013 (7)	0.023 (9)	0.003 (6)	0.003 (8)	0.004 (7)
C36	0.025 (8)	0.014 (7)	0.025 (10)	0.004 (6)	0.006 (8)	0.007 (7)

Geometric parameters (Å, º) top

Br11—C11	1.866 (17)	C23—H23	0.9300
C11—C12	1.38 (2)	Br24—C24	1.882 (18)
C11—C16	1.43 (2)	C24—C25	1.41 (3)
Br12—C12	1.896 (17)	C25—C26	1.37 (2)
C12—C13	1.38 (2)	C25—H25	0.9300
C13—C14	1.39 (2)	C26—H26	0.9300
C13—H13	0.9300	Br31—C31	1.898 (18)
Br14—C14	1.908 (18)	C31—C32	1.36 (2)
C14—C15	1.35 (2)	C31—C36	1.37 (2)
C15—C16	1.42 (2)	Br32—C32	1.896 (17)
C15—H15	0.9300	C32—C33	1.43 (2)
C16—H16	0.9300	C33—C34	1.39 (2)
Br21—C21	1.883 (18)	C33—H33	0.9300
C21—C26	1.39 (2)	Br34—C34	1.906 (18)
C21—C22	1.40 (2)	C34—C35	1.36 (2)
Br22—C22	1.884 (18)	C35—C36	1.42 (2)
C22—C23	1.38 (2)	C35—H35	0.9300
C23—C24	1.37 (2)	C36—H36	0.9300

C12—C11—C16	118.9 (16)	C23—C24—C25	120.1 (17)
C12—C11—Br11	123.9 (13)	C23—C24—Br24	120.6 (14)
C16—C11—Br11	117.2 (14)	C25—C24—Br24	119.3 (14)
C11—C12—C13	122.1 (16)	C26—C25—C24	118.8 (18)
C11—C12—Br12	120.2 (13)	C26—C25—H25	120.6
C13—C12—Br12	117.6 (14)	C24—C25—H25	120.6
C12—C13—C14	118.0 (18)	C25—C26—C21	121.7 (18)
C12—C13—H13	121.0	C25—C26—H26	119.2
C14—C13—H13	121.0	C21—C26—H26	119.2
C15—C14—C13	122.7 (18)	C32—C31—C36	121.0 (17)
C15—C14—Br14	120.0 (14)	C32—C31—Br31	121.1 (14)
C13—C14—Br14	117.2 (15)	C36—C31—Br31	117.9 (14)
C14—C15—C16	120.0 (17)	C31—C32—C33	121.0 (17)
C14—C15—H15	120.0	C31—C32—Br32	123.0 (14)
C16—C15—H15	120.0	C33—C32—Br32	116.1 (14)
C15—C16—C11	118.2 (17)	C34—C33—C32	116.0 (18)
C15—C16—H16	120.9	C34—C33—H33	122.0
C11—C16—H16	120.9	C32—C33—H33	122.0
C26—C21—C22	118.3 (17)	C35—C34—C33	124.2 (18)
C26—C21—Br21	118.9 (14)	C35—C34—Br34	119.3 (13)
C22—C21—Br21	122.7 (14)	C33—C34—Br34	116.5 (14)
C23—C22—C21	120.4 (17)	C34—C35—C36	117.5 (17)
C23—C22—Br22	119.4 (15)	C34—C35—H35	121.3
C21—C22—Br22	120.1 (14)	C36—C35—H35	121.3
C24—C23—C22	120.6 (18)	C31—C36—C35	120.4 (18)
C24—C23—H23	119.7	C31—C36—H36	119.8
C22—C23—H23	119.7	C35—C36—H36	119.8

C16—C11—C12—C13	1 (3)	C22—C23—C24—Br24	−179.0 (14)
Br11—C11—C12—C13	−178.2 (15)	C23—C24—C25—C26	0 (3)
C16—C11—C12—Br12	−174.9 (13)	Br24—C24—C25—C26	−179.1 (15)
Br11—C11—C12—Br12	6 (2)	C24—C25—C26—C21	−3 (3)
C11—C12—C13—C14	0 (3)	C22—C21—C26—C25	3 (3)
Br12—C12—C13—C14	176.0 (14)	Br21—C21—C26—C25	179.8 (16)
C12—C13—C14—C15	0 (3)	C36—C31—C32—C33	2 (3)
C12—C13—C14—Br14	−177.7 (15)	Br31—C31—C32—C33	179.6 (15)
C13—C14—C15—C16	0 (3)	C36—C31—C32—Br32	−177.3 (14)
Br14—C14—C15—C16	177.1 (13)	Br31—C31—C32—Br32	1 (2)
C14—C15—C16—C11	1 (3)	C31—C32—C33—C34	−2 (3)
C12—C11—C16—C15	−2 (3)	Br32—C32—C33—C34	177.4 (14)
Br11—C11—C16—C15	177.8 (13)	C32—C33—C34—C35	2 (3)
C26—C21—C22—C23	−1 (3)	C32—C33—C34—Br34	−179.1 (14)
Br21—C21—C22—C23	−177.7 (14)	C33—C34—C35—C36	−2 (3)
C26—C21—C22—Br22	−179.0 (13)	Br34—C34—C35—C36	179.0 (14)
Br21—C21—C22—Br22	5 (2)	C32—C31—C36—C35	−2 (3)
C21—C22—C23—C24	−1 (3)	Br31—C31—C36—C35	−179.8 (14)
Br22—C22—C23—C24	176.5 (14)	C34—C35—C36—C31	2 (3)
C22—C23—C24—C25	2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···Br12ⁱ	0.93	2.97	3.66 (2)	133
C33—H33···Br22ⁱⁱ	0.93	3.04	3.88 (2)	152
C35—H35···Br12ⁱⁱⁱ	0.93	3.00	3.723 (19)	136

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

(135TBB_270K) top

Crystal data top

C₆H₃Br₃	D_x = 2.679 Mg m⁻³
M_r = 314.78	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 2027 reflections
a = 4.06406 (18) Å	θ = 4.2–24.7°
b = 13.5231 (6) Å	µ = 15.41 mm⁻¹
c = 14.1996 (6) Å	T = 270 K
V = 780.39 (6) Å³	Needle, yellow
Z = 4	0.35 × 0.16 × 0.10 mm
F(000) = 576

Data collection top

Xcalibur, Eos diffractometer	1520 independent reflections
Radiation source: fine-focus sealed X-ray tube	1297 reflections with I > 2σ(I)
Detector resolution: 16.1544 pixels mm^-1	R_int = 0.067
ω scans	θ_max = 26.0°, θ_min = 2.9°
Absorption correction: analytical CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −5→5
T_min = 0.072, T_max = 0.274	k = −16→16
10906 measured reflections	l = −17→17

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.030	w = 1/[σ²(F_o²) + (0.021P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.056	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.49 e Å⁻³
1520 reflections	Δρ_min = −0.46 e Å⁻³
84 parameters	Extinction correction: SHELXL-2014/7 (Sheldrick 2014), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0136 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Refined as an inversion twin.
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.45 (4)

Special details top

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
C11	0.2972 (17)	0.2294 (5)	0.3353 (5)	0.0360 (17)
Br11	0.43632 (19)	0.10886 (5)	0.39102 (6)	0.0506 (3)
C12	0.1386 (16)	0.2265 (5)	0.2502 (5)	0.0369 (17)
H12	0.0990	0.1668	0.2198	0.044*
C13	0.0397 (16)	0.3146 (5)	0.2110 (4)	0.0354 (15)
Br13	−0.17512 (18)	0.31297 (6)	0.09293 (5)	0.0491 (2)
C14	0.1000 (15)	0.4037 (5)	0.2539 (5)	0.0367 (17)
H14	0.0354	0.4627	0.2258	0.044*
C15	0.2591 (17)	0.4036 (5)	0.3398 (5)	0.0395 (18)
Br15	0.35063 (19)	0.52405 (5)	0.40091 (7)	0.0555 (3)
C16	0.3652 (15)	0.3164 (5)	0.3816 (5)	0.0380 (16)
H16	0.4777	0.3168	0.4386	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.042 (4)	0.039 (4)	0.027 (4)	0.004 (4)	0.003 (4)	0.003 (3)
Br11	0.0590 (5)	0.0397 (4)	0.0530 (5)	0.0067 (4)	−0.0033 (4)	0.0058 (4)
C12	0.038 (4)	0.037 (4)	0.036 (4)	−0.005 (3)	0.010 (3)	−0.005 (3)
C13	0.031 (4)	0.046 (4)	0.029 (3)	−0.004 (4)	0.004 (3)	−0.006 (4)
Br13	0.0522 (4)	0.0626 (5)	0.0326 (4)	−0.0040 (4)	−0.0028 (4)	0.0031 (4)
C14	0.036 (4)	0.038 (4)	0.037 (4)	0.000 (3)	0.003 (3)	0.001 (3)
C15	0.038 (4)	0.033 (4)	0.047 (5)	−0.003 (4)	0.001 (4)	0.000 (3)
Br15	0.0655 (5)	0.0383 (4)	0.0625 (6)	−0.0071 (4)	−0.0088 (6)	−0.0090 (4)
C16	0.035 (4)	0.044 (4)	0.035 (4)	−0.004 (3)	0.001 (3)	−0.003 (4)

Geometric parameters (Å, º) top

C11—C12	1.371 (9)	C13—Br13	1.891 (6)
C11—C16	1.376 (9)	C14—C15	1.380 (10)
C11—Br11	1.898 (7)	C14—H14	0.9300
C12—C13	1.375 (9)	C15—C16	1.388 (9)
C12—H12	0.9300	C15—Br15	1.883 (7)
C13—C14	1.371 (9)	C16—H16	0.9300

C12—C11—C16	122.7 (6)	C13—C14—C15	118.3 (7)
C12—C11—Br11	118.9 (5)	C13—C14—H14	120.8
C16—C11—Br11	118.4 (5)	C15—C14—H14	120.8
C11—C12—C13	118.0 (6)	C14—C15—C16	121.6 (7)
C11—C12—H12	121.0	C14—C15—Br15	119.9 (6)
C13—C12—H12	121.0	C16—C15—Br15	118.4 (5)
C14—C13—C12	122.0 (6)	C11—C16—C15	117.4 (6)
C14—C13—Br13	119.1 (5)	C11—C16—H16	121.3
C12—C13—Br13	118.9 (5)	C15—C16—H16	121.3

C16—C11—C12—C13	−1.2 (10)	C13—C14—C15—C16	1.8 (10)
Br11—C11—C12—C13	180.0 (5)	C13—C14—C15—Br15	179.5 (5)
C11—C12—C13—C14	1.0 (10)	C12—C11—C16—C15	1.6 (10)
C11—C12—C13—Br13	179.3 (5)	Br11—C11—C16—C15	−179.6 (5)
C12—C13—C14—C15	−1.3 (10)	C14—C15—C16—C11	−1.8 (10)
Br13—C13—C14—C15	−179.6 (5)	Br15—C15—C16—C11	−179.6 (5)

(135TBB_200K) top

Crystal data top

C₆H₃Br₃	D_x = 2.717 Mg m⁻³
M_r = 314.78	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 2709 reflections
a = 4.03673 (14) Å	θ = 4.2–27.7°
b = 13.4739 (4) Å	µ = 15.63 mm⁻¹
c = 14.1499 (5) Å	T = 200 K
V = 769.62 (4) Å³	Needle, yellow
Z = 4	0.35 × 0.16 × 0.10 mm
F(000) = 576

Data collection top

Xcalibur, Eos diffractometer	1496 independent reflections
Radiation source: fine-focus sealed X-ray tube	1370 reflections with I > 2σ(I)
Detector resolution: 16.1544 pixels mm^-1	R_int = 0.055
ω scans	θ_max = 26.0°, θ_min = 2.9°
Absorption correction: analytical CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −4→4
T_min = 0.073, T_max = 0.274	k = −16→16
10781 measured reflections	l = −17→17

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.022	w = 1/[σ²(F_o²) + (0.0113P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.037	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.35 e Å⁻³
1496 reflections	Δρ_min = −0.30 e Å⁻³
84 parameters	Extinction correction: SHELXL-2014/7 (Sheldrick 2014), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0022 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Refined as an inversion twin.
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.49 (3)

Special details top

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
C11	0.2979 (12)	0.2280 (4)	0.3360 (4)	0.0247 (12)
Br11	0.43826 (13)	0.10723 (4)	0.39149 (4)	0.03496 (16)
C12	0.1354 (11)	0.2249 (4)	0.2501 (3)	0.0247 (12)
H12	0.0929	0.1650	0.2199	0.030*
C13	0.0382 (12)	0.3143 (4)	0.2109 (3)	0.0249 (11)
Br13	−0.18039 (13)	0.31242 (4)	0.09253 (4)	0.03417 (15)
C14	0.0968 (11)	0.4038 (4)	0.2543 (4)	0.0258 (12)
H14	0.0281	0.4631	0.2269	0.031*
C15	0.2620 (12)	0.4030 (4)	0.3403 (4)	0.0268 (13)
Br15	0.35318 (13)	0.52453 (4)	0.40151 (5)	0.03821 (17)
C16	0.3655 (11)	0.3155 (4)	0.3824 (3)	0.0277 (11)
H16	0.4766	0.3158	0.4400	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.022 (2)	0.023 (3)	0.029 (3)	0.000 (3)	0.007 (3)	0.002 (2)
Br11	0.0405 (3)	0.0270 (3)	0.0374 (3)	0.0045 (2)	−0.0026 (3)	0.0041 (3)
C12	0.026 (3)	0.023 (3)	0.025 (3)	−0.002 (2)	0.004 (2)	−0.004 (2)
C13	0.021 (3)	0.033 (3)	0.020 (3)	−0.003 (3)	0.002 (2)	−0.002 (3)
Br13	0.0364 (3)	0.0434 (3)	0.0226 (3)	−0.0025 (3)	−0.0017 (3)	0.0021 (3)
C14	0.026 (3)	0.026 (3)	0.025 (3)	−0.003 (2)	0.003 (2)	0.000 (2)
C15	0.025 (3)	0.022 (3)	0.034 (3)	−0.005 (2)	0.004 (2)	−0.002 (2)
Br15	0.0452 (3)	0.0254 (3)	0.0440 (4)	−0.0049 (2)	−0.0058 (3)	−0.0063 (3)
C16	0.028 (3)	0.034 (3)	0.021 (3)	−0.003 (2)	0.001 (2)	0.002 (3)

Geometric parameters (Å, º) top

C11—C16	1.376 (7)	C13—Br13	1.894 (5)
C11—C12	1.382 (7)	C14—C15	1.388 (7)
C11—Br11	1.894 (5)	C14—H14	0.9300
C12—C13	1.383 (7)	C15—C16	1.386 (7)
C12—H12	0.9300	C15—Br15	1.889 (5)
C13—C14	1.374 (7)	C16—H16	0.9300

C16—C11—C12	122.7 (5)	C13—C14—C15	117.9 (5)
C16—C11—Br11	118.6 (4)	C13—C14—H14	121.1
C12—C11—Br11	118.7 (4)	C15—C14—H14	121.1
C11—C12—C13	117.5 (4)	C16—C15—C14	121.9 (5)
C11—C12—H12	121.3	C16—C15—Br15	118.8 (4)
C13—C12—H12	121.3	C14—C15—Br15	119.2 (4)
C14—C13—C12	122.4 (4)	C11—C16—C15	117.6 (4)
C14—C13—Br13	119.2 (4)	C11—C16—H16	121.2
C12—C13—Br13	118.4 (4)	C15—C16—H16	121.2

C16—C11—C12—C13	−0.2 (7)	C13—C14—C15—C16	−0.2 (7)
Br11—C11—C12—C13	−179.5 (3)	C13—C14—C15—Br15	179.1 (4)
C11—C12—C13—C14	−0.2 (7)	C12—C11—C16—C15	0.4 (7)
C11—C12—C13—Br13	179.2 (3)	Br11—C11—C16—C15	179.7 (4)
C12—C13—C14—C15	0.4 (7)	C14—C15—C16—C11	−0.2 (7)
Br13—C13—C14—C15	−179.0 (3)	Br15—C15—C16—C11	−179.5 (4)

(135TBB_100K) top

Crystal data top

C₆H₃Br₃	D_x = 2.763 Mg m⁻³
M_r = 314.78	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 3792 reflections
a = 4.00341 (11) Å	θ = 4.2–30.8°
b = 13.4119 (3) Å	µ = 15.90 mm⁻¹
c = 14.0916 (4) Å	T = 100 K
V = 756.63 (3) Å³	Needle, yellow
Z = 4	0.35 × 0.16 × 0.10 mm
F(000) = 576

Data collection top

Xcalibur, Eos diffractometer	1476 independent reflections
Radiation source: fine-focus sealed X-ray tube	1395 reflections with I > 2σ(I)
Detector resolution: 16.1544 pixels mm^-1	R_int = 0.049
ω scans	θ_max = 26.0°, θ_min = 2.9°
Absorption correction: analytical CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −4→4
T_min = 0.074, T_max = 0.274	k = −16→16
10543 measured reflections	l = −17→17

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.018	w = 1/[σ²(F_o²) + (0.0137P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.036	(Δ/σ)_max = 0.001
S = 1.01	Δρ_max = 0.34 e Å⁻³
1476 reflections	Δρ_min = −0.37 e Å⁻³
84 parameters	Extinction correction: SHELXL-2014/7 (Sheldrick 2014), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00088 (19)
Primary atom site location: structure-invariant direct methods	Absolute structure: Refined as an inversion twin.
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.48 (3)

Special details top

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
C11	0.2985 (12)	0.2268 (3)	0.3364 (3)	0.0142 (11)
Br11	0.44078 (12)	0.10520 (3)	0.39217 (4)	0.01827 (14)
C12	0.1347 (11)	0.2240 (3)	0.2501 (3)	0.0142 (11)
H12	0.0941	0.1639	0.2192	0.017*
C13	0.0339 (12)	0.3134 (4)	0.2116 (3)	0.0146 (10)
Br13	−0.18586 (12)	0.31174 (4)	0.09210 (4)	0.01805 (13)
C14	0.0941 (11)	0.4039 (4)	0.2543 (4)	0.0158 (11)
H14	0.0253	0.4633	0.2266	0.019*
C15	0.2615 (11)	0.4028 (4)	0.3404 (4)	0.0165 (11)
Br15	0.35576 (11)	0.52517 (3)	0.40228 (4)	0.01976 (14)
C16	0.3671 (11)	0.3151 (4)	0.3831 (3)	0.0150 (10)
H16	0.4796	0.3156	0.4408	0.018*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.014 (2)	0.011 (2)	0.019 (3)	0.001 (2)	0.004 (2)	0.004 (2)
Br11	0.0209 (3)	0.0134 (2)	0.0204 (3)	0.0022 (2)	−0.0012 (2)	0.0019 (2)
C12	0.015 (2)	0.012 (2)	0.016 (3)	−0.001 (2)	0.004 (2)	−0.002 (2)
C13	0.012 (2)	0.021 (2)	0.011 (2)	−0.002 (2)	0.001 (2)	−0.001 (2)
Br13	0.0195 (2)	0.0215 (2)	0.0132 (3)	−0.0014 (2)	−0.0011 (2)	0.0008 (2)
C14	0.015 (3)	0.015 (3)	0.017 (3)	0.000 (2)	0.003 (2)	0.002 (2)
C15	0.015 (3)	0.015 (3)	0.020 (3)	−0.005 (2)	0.006 (2)	−0.003 (2)
Br15	0.0234 (3)	0.0125 (2)	0.0233 (3)	−0.0023 (2)	−0.0030 (3)	−0.0031 (2)
C16	0.012 (2)	0.020 (2)	0.013 (2)	−0.002 (2)	−0.0023 (19)	−0.003 (2)

Geometric parameters (Å, º) top

C11—C12	1.382 (7)	C13—Br13	1.900 (4)
C11—C16	1.383 (6)	C14—C15	1.386 (7)
C11—Br11	1.898 (5)	C14—H14	0.9300
C12—C13	1.377 (7)	C15—C16	1.387 (7)
C12—H12	0.9300	C15—Br15	1.896 (5)
C13—C14	1.376 (7)	C16—H16	0.9300

C12—C11—C16	122.5 (4)	C13—C14—C15	117.3 (5)
C12—C11—Br11	118.9 (4)	C13—C14—H14	121.3
C16—C11—Br11	118.6 (4)	C15—C14—H14	121.3
C13—C12—C11	117.5 (4)	C14—C15—C16	122.3 (5)
C13—C12—H12	121.2	C14—C15—Br15	119.3 (4)
C11—C12—H12	121.2	C16—C15—Br15	118.3 (4)
C14—C13—C12	123.0 (4)	C11—C16—C15	117.4 (4)
C14—C13—Br13	118.7 (4)	C11—C16—H16	121.3
C12—C13—Br13	118.3 (3)	C15—C16—H16	121.3

C16—C11—C12—C13	−1.1 (7)	C13—C14—C15—C16	0.1 (7)
Br11—C11—C12—C13	179.8 (3)	C13—C14—C15—Br15	179.4 (4)
C11—C12—C13—C14	1.1 (7)	C12—C11—C16—C15	0.6 (7)
C11—C12—C13—Br13	179.1 (3)	Br11—C11—C16—C15	179.7 (3)
C12—C13—C14—C15	−0.6 (7)	C14—C15—C16—C11	−0.1 (7)
Br13—C13—C14—C15	−178.6 (3)	Br15—C15—C16—C11	−179.4 (4)

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