1-Chloro-4-[2-(4-chloro­phen­yl)eth­yl]benzene and its bromo analogue: crystal structure, Hirshfeld surface analysis and computational chemistry

Two independent mol­ecules comprise the asymmetric unit of the chloro compound, each disposed about a centre of inversion. Each mol­ecule approximates mirror symmetry. By contrast, the bromo compound is significantly twisted [dihedral angle between the benzene rings = 59.29 (11)° cf. 0° for the chloro-containing mol­ecules].

Abstract

The crystal and mol­ecular structures of C₁₄H₁₂Cl₂, (I), and C₁₄H₁₂Br₂, (II), are described. The asymmetric unit of (I) comprises two independent mol­ecules, A and B, each disposed about a centre of inversion. Each mol­ecule approximates mirror symmetry [the C_b—C_b—C_e—C_e torsion angles = −83.46 (19) and 95.17 (17)° for A, and −83.7 (2) and 94.75 (19)° for B; b = benzene and e = ethyl­ene]. By contrast, the mol­ecule in (II) is twisted, as seen in the dihedral angle of 59.29 (11)° between the benzene rings cf. 0° in (I). The mol­ecular packing of (I) features benzene-C—H⋯π(benzene) and Cl⋯Cl contacts that lead to an open three-dimensional (3D) architecture that enables twofold 3D–3D inter­penetration. The presence of benzene-C—H⋯π(benzene) and Br⋯Br contacts in the crystal of (II) consolidate the 3D architecture. The analysis of the calculated Hirshfeld surfaces confirm the influence of the benzene-C—H⋯π(benzene) and X⋯X contacts on the mol­ecular packing and show that, to a first approximation, H⋯H, C⋯H/H⋯C and C⋯X/X⋯C contacts dominate the packing, each contributing about 30% to the overall surface in each of (I) and (II). The analysis also clearly differentiates between the A and B mol­ecules of (I).

Chemical context  

The synthesis and physical characterization of the title compound, 1-chloro-4-[2-(4-chloro­phen­yl)eth­yl]benzene, C₁₄H₁₂Cl₂, (I), has been reported by several research groups over the years (Otsubo et al., 1980 ▸; Bestiuc et al., 1985 ▸; Parnes et al., 1989 ▸; Hu et al., 2011 ▸; Liu & Li, 2007 ▸). In the same way, the bromo analogue of (I), 1-bromo-4-[2-(4-bromo­phen­yl)eth­yl]benzene, C₁₄H₁₂Br₂, (II), has been described previously (Golden, 1961 ▸; Otsubo et al., 1980 ▸; Remizov et al., 2005 ▸; Liu & Li, 2007 ▸). Despite this inter­est, crystallographic characterization is lacking. Recently, compounds (I) and (II) became available as minor side-products during the synthesis of the respective tri(4-halobenz­yl)tin hydroxide from the reaction of tri(4-halobenz­yl)tin halide and sodium hydroxide. Herein, the crystal and mol­ecular structures of (I) and (II) are described. The structures are not isostructural and in order to gain further insight into the mol­ecular packing, the structures were subjected to an analysis of their Hirshfeld surfaces along with some computational chemistry.

Structural commentary  

The two independent mol­ecules comprising the asymmetric unit of (I) are shown in Fig. 1 ▸(a) and (b); each is disposed about a centre of inversion. The mol­ecules present very similar features and, from inversion symmetry, comprise parallel benzene rings. The C3A—C4A—C7A—C7A ⁱ and C5A—C4A—C7A—C7A ⁱ torsion angles of −83.46 (19) and 95.17 (17)° highlight deviations from mirror symmetry in the mol­ecule [symmetry operation: (i) 1 − x, 1 − y, 1 − z]. These values are equal within experimental error and are very close to the equivalent angles for the second independent mol­ecule of −83.7 (2) and 94.75 (19)°, respectively [symmetry operation: (ii)  − x,  − y, 1 − z].

Figure 1.

The mol­ecular structures of (a) the Cl1A-containing mol­ecule of (I), (b) the Cl1B-containing mol­ecule of (I) and (c) the mol­ecule of (II) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level. Unlabelled atoms in (a) and (b) are related by the symmetry operations 1 − x, 1 − y, 1 − z and  − x,  − y, 1 − z, respectively.

The mol­ecule of (II) is shown in Fig. 1 ▸(c) and does not feature the mol­ecular symmetry of (I). The difference in the conformation in (II), cf. (I), is seen immediately in the magnitude of the dihedral angle formed between the benzene rings of 59.29 (11)°, indicating an inclined disposition. The central torsion angle, i.e. C4—C7—C8—C9 of 172.1 (2)°, deviates from the 180° angles observed for the two independent mol­ecules in (I). The twist in the mol­ecule of (II) is reflected in the four torsion angles C3—C4—C7—C8 [46.6 (3)°], C5—C4—C7—C8 [−134.8 (2)°], C7—C8—C9—C14 [16.4 (3)°] and C7—C8—C9—C10 [−163.7 (2)°].

The conformational differences between the mol­ecules in (I) and (II) are highlighted in the overlay diagram shown in Fig. 2 ▸.

Figure 2.

Overlap diagram of the (a) Cl1A-mol­ecule in (I) (red image), (b) Cl1B-mol­ecule in (I) (green) and (c) the mol­ecule in (II) (blue). Mol­ecules have been overlapped so that the C1-benzene rings are coincident.

Supra­molecular features  

In the crystal of (I), the main point of contact between the independent mol­ecules comprising the asymmetric unit are of the type benzene-C—H⋯π(benzene), Table 1 ▸. The result is the formation of a supra­molecular chain along the a-axis direction. Chains are connected into a supra­molecular layer via end-on Cl1A⋯Cl1A ⁱⁱⁱ contacts [3.3184 (7) Å and C1—C11A⋯Cl1A ⁱⁱⁱ = 164.61 (5)° for symmetry operation (iii)  − x,  − y, −z], Fig. 3 ▸(a). The topology of the layer is flat and connections between the layers that stack along [10] are weaker end-on Cl1B⋯Cl1B ^iv contacts [3.4322 (7) Å and C1B—Cl1B⋯Cl1B ^iv = 155.19 (5)° for symmetry operation (iv) 1 − x, 2 − y, 2 − z], which lead to a three-dimensional (3-D) architecture. As seen from Fig, 3(b), there are large voids defined by the aforementioned contacts which enables twofold, 3D–3D inter­penetration, Fig. 3 ▸(c).

Table 1. Hydrogen-bond geometry (Å, °) for (I) .

Cg1 is the centroid of the (C1A–C6A) ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5B—H5B⋯Cg1	0.93	2.62	3.4866 (15)	155

Figure 3.

Mol­ecular packing in (I): (a) a view of the supra­molecular layer parallel to [10] sustained by C—H⋯π and Cl⋯Cl contacts shown as purple and orange dashed lines, respectively, (b) a view of half of the unit-cell contents shown in projection down the c axis and (c) an image highlighting the twofold inter­penetration in space-filling mode.

The 3-D architecture of (II) is supported by benzene-C—H⋯π(benzene) and Br⋯Br contacts. Globally, mol­ecules assemble in the ac plane and are connected to layers along [010] by benzene-C—H⋯π(benzene) contacts, Table 2 ▸. Further, lateral inter­actions are Br1⋯Br2ⁱ [3.5242 (4) Å, C1—Br⋯Br2ⁱ = 144.67 (7)° and C12ⁱ—Br2ⁱ⋯Br1 = 154.39 (7)° for symmetry operation (i) 1 + x, y, 1 + z; Fig. 4 ▸].

Table 2. Hydrogen-bond geometry (Å, °) for (II) .

Cg1 and Cg2 are the centroids of the (C1–C6) and (C9–C14) rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg2i	0.95	2.69	3.442 (2)	136
C6—H6⋯Cg1ii	0.95	2.91	3.704 (2)	141
C13—H13⋯Cg2iii	0.95	2.87	3.569 (2)	131

Symmetry codes: (i) ; (ii) ; (iii) .

Figure 4.

Mol­ecular packing in (II): a view of the unit-cell contents shown in projection down the a axis, highlighting C—H⋯π and Br⋯Br contacts as purple and orange dashed lines, respectively.

Hirshfeld surface analysis  

The Hirshfeld surface calculations for (I) and (II) were performed in accord with established procedures (Tan et al., 2019 ▸) with the aid of Crystal Explorer (Turner et al., 2017 ▸) to determine the influence of weak inter­molecular inter­actions upon the mol­ecular packing in the absence of conventional hydrogen bonds.

In the crystal of (I), with two independent mol­ecules, labelled A and B, disposed about a centre of inversion the presence of faint-red spots near the benzene-C2A, C3A and H5B atoms in the images of Hirshfeld surfaces mapped over d _norm in Fig. 5 ▸ represent C—H⋯π contacts, Tables 1 ▸ and 3 ▸. The diminutive red spot viewed near the benzene-C5B atom in Fig. 5 ▸(b) indicates the effect of a short inter­atomic C5B⋯H2B contact, Table 3 ▸. Also, the presence of diminutive red spots near the terminal chlorine atoms of both independent mol­ecules in Fig. 5 ▸ are due to the formation of short inter­atomic Cl⋯Cl contacts, Table 3 ▸.

Figure 5.

Views of the Hirshfeld surfaces for (I) mapped over d _norm for (a) mol­ecule A [in the range −0.103 to +1.259 arbitrary units] and (b) mol­ecule B [−0.072 to +1.234 arbitrary units] highlighting the short inter­atomic C⋯H/H⋯C and H⋯H contacts through black and red dashed lines, respectively.

Table 3. Summary of short inter­atomic contacts (Å) in (I)^a .

Contact	Distance	Symmetry operation
(I)
H6B⋯H72A	2.35	x, y, z
H5B⋯C2A	2.75	x, y, z
H5B⋯C3A	2.72	x, y, z
H2B⋯C5B	2.67	x, 2 − y,  + z
C11A⋯Cl1A	3.3184 (7)	− x,  − y, −z
Cl1B⋯Cl1B	3.4322 (7)	1 − x, 2 − y, 2 − z
(II)
H8B⋯H8B	2.21	−x, 2 − y, 1 − z
H3⋯C13	2.74	−x, 1 − y, 1 − z
H3⋯C14	2.72	−x, 1 − y, 1 − z
H6⋯C1	2.82	1 − x,  + y,  − z
H6⋯C2	2.62	1 − x,  + y,  − z
H11⋯C6	2.80	−x, 2 − y, 1 − z
Br1⋯Br2	3.5242 (4)	1 + x, y, 1 + z

Notes: (a) The inter­atomic distances are calculated in Crystal Explorer (Turner et al., 2017 ▸) whereby the X—H bond lengths are adjusted to their neutron values.

In the crystal of (II), the bright-red spots near the bromine atoms on the Hirshfeld surfaces mapped over d _norm in Fig. 6 ▸ indicate inter­atomic Br⋯Br contacts, Table 3 ▸, whereas those near the benzene-C2 and H6 atoms in Fig. 6 ▸(b) indicate short inter­atomic C—H⋯π inter­actions, Table 3 ▸. The presence of faint-red spots near the benzene-C13, C14 and H3 atoms in Fig. 6 ▸(a) also reflect the presence of C—H⋯π contacts, Table 3 ▸.

Figure 6.

Views of the Hirshfeld surfaces for (II) mapped over d _norm [in the range −0.104 to +1.172 arbitrary units] highlighting the short inter­atomic C⋯H/H⋯C contacts through black dashed lines.

From the views of Hirshfeld surfaces mapped over the calculated electrostatic potentials in Figs. 7 ▸(a) and (b) for the independent mol­ecules of (I) highlight the small deviations from putative mirror symmetry through the slight differences in the blue and red regions around the atoms of their surfaces corresponding, respectively, to positive and negative potentials. For (II), Fig.7(c), the donors and acceptors of the C—H⋯π inter­actions are viewed as blue bumps and light-red concave regions. Further, the donors and acceptors of the C—H⋯π contacts for each of (I) and (II) are also illustrated through black dotted lines on the Hirshfeld surfaces mapped with shape-index properties in Fig. 8 ▸.

Figure 7.

Views of the Hirshfeld surfaces mapped over the calculated electrostatic potential for (a) (I), mol­ecule A [−0.032 to +0.035 a.u.], (b) (I), mol­ecule B in [−0.033 to +0.044 a.u.] range and (c) (II) [−0.022 to +0.039 a.u.]. The red and blue regions represent negative and positive electrostatic potentials, respectively.

Figure 8.

Views of the Hirshfeld surfaces mapped with the shape index property for (a) (I), mol­ecule B, (b)–(d) (II), highlighting inter­molecular C—H⋯π inter­actions through black dotted lines.

The overall two-dimensional fingerprint plot for the independent mol­ecules A and B as well as entire (I) are shown in Fig. 9 ▸(a), and those delineated into H⋯H, C⋯H/H⋯C, Cl⋯H/H⋯Cl and Cl⋯Cl contacts are illustrated in Fig. 9 ▸(b)–(e), respectively. The qu­anti­tative summary of percentage contributions from the different inter­atomic contacts to the respective Hirshfeld surfaces of A, B and (I) are presented in Table 4 ▸.

Figure 9.

(a) The full two-dimensional fingerprint plot for mol­ecule A of (I), mol­ecule B of (I), and overall (I), and (b)–(e) those delineated into H⋯H, C⋯H/H⋯C, Cl⋯H/H⋯Cl and Cl⋯Cl contacts.

Table 4. Percentage contributions of inter­atomic contacts to the Hirshfeld surface for (I) and (II).

Contact	Percentage contribution
	(I) - mol­ecule A	(I) - mol­ecule B	(I)	(II)
H⋯H	30.8	35.1	31.4	30.6
C⋯H/H⋯C	32.5	27.0	28.4	32.7
X⋯H/H⋯X	30.5	33.3	34.2	30.4
X⋯X	3.9	2.2	3.4	4.9
C⋯C	1.3	1.3	1.4	0.0
C⋯X/X⋯C	1.1	1.1	1.2	1.4

Some qualitative differences in the fingerprint plots are evident for mol­ecules A and B, confirming their distinct packing inter­actions. The complementary pair of forceps-like tips at d _e + d _i ∼2.3 Å in the fingerprint plots delineated into H⋯H contacts for A and B in Fig. 9 ▸(b) represent the short inter­atomic H⋯H contact, Table 3 ▸, which merge to form a pair of tips in the overall plot for (I). The fingerprint plots delineated into C⋯H/H⋯C contacts for mol­ecules A and B in Fig. 9 ▸(c) exhibit the clearest distinction between the inter­atomic contacts formed by the mol­ecules through the asymmetric distribution of points. The complementary distribution of points in the acceptor and donor regions of the plots for A and B, respectively, with the peaks at d _e + d _i ∼2.7 Å, are due to the formation of short inter­atomic C⋯H/H⋯C contacts between the benzene-C2A, C3A and H5B atoms, Table 3 ▸. Similar short inter­atomic contacts between benzene-C5B and H2B atoms of B results in forceps-like tips at d _e + d _i ∼2.7 Å in the acceptor region of the plot whereas it is merged within the tip of previously mentioned contact in the donor region. However, the respective plot for an overall structure is symmetric owing to the merging of the asymmetric distribution of points. The significant and quite similar contributions from Cl⋯H/H⋯Cl contacts to the Hirshfeld surfaces of A, B and overall (I), Fig. 9 ▸(d), have very little influence on the mol­ecular packing due to their inter­atomic distances being equal to or greater than the sum of their van der Waals radii. The linear distribution of points beginning from d _e + d _i ∼3.3 and 3.4 Å, Fig. 9 ▸(e), in the Cl⋯Cl delineated plots for A and B, respectively, indicate the presence of Cl⋯Cl inter­actions. The small contribution from C⋯C contacts to the Hirshfeld surface of (I) has a negligible effect on the packing.

Comparable fingerprint plots for (II) are shown in Fig. 10 ▸ and percentage contributions are collected in Table 4 ▸. The short inter­atomic H⋯H contact between symmetry-related ethyl­ene-H8B atoms is viewed as a single peak at d _e + d _i ∼2.2 Å in Fig. 10 ▸(b). In Fig. 10 ▸(c), delineated into C⋯H/H⋯C contacts, Table 3 ▸, the forceps-like tips at d _e + d _i ∼2.6 Å reflect the significant C—H⋯π contacts in the mol­ecular packing. The contribution of Br⋯H/H⋯Br contacts to the Hirshfeld surface of (II), Fig. 10 ▸(d), have very little influence on the packing due to their inter­atomic distances being around the sum of their van der Waals radii. The short inter­atomic Br⋯Br contacts in (II) are viewed as a thin, linear distribution of points initiating from d _e + d _i ∼3.5 Å, Fig. 10 ▸(e). As for (I), the small contribution from C⋯C contacts to the Hirshfeld surface of (II) has a negligible effect in the crystal.

Figure 10.

(a) The full two-dimensional fingerprint plot for (II), and (b)–(e) those delineated into H⋯H, C⋯H/H⋯C, Br⋯Br and Br⋯H/H⋯Br contacts.

Computational chemistry  

The pairwise inter­action energies between the mol­ecules in the crystals of (I) and (II) were calculated by summing up four energy components, being electrostatic (E _ele), polarization (E _pol), dispersion (E _dis) and exchange-repulsion (E _rep) (Turner et al., 2017 ▸). These energies were obtained by using the wave functions calculated at the B3LYP/6-31G(d,p) level theory for (I) and the HF/STO-3G level theory for (II). The individual energy components as well as total inter­action energy relative to reference mol­ecule within mol­ecular clusters out to 3.8 Å. The nature and strength of the energies for the key identified inter­molecular inter­actions are qu­anti­tatively summarized in Table 5 ▸. Dispersive components are dominant as conventional hydrogen bonding is not possible.

Table 5. Summary of inter­action energies (kJ mol⁻¹) calculated for (I) and (II).

Contact	E ele	E pol	E dis	E rep	E tot
(I)
Cl1A⋯Cl1A	−0.9	0.0	−3.3	7.6	0.9
Cl1B⋯Cl1B	−0.9	−0.1	−3.4	5.8	−0.4
C5—H5⋯Cg(C1A–C6A)	−8.5	−1.5	−33.5	26.1	−23.1
C5⋯H2B	−3.7	−0.8	−18.2	12.9	−12.3
(II)
Br1⋯Br2	−2.2	−0.1	−4.9	8.4	0.1
C3—H3⋯Cg(C9–C14)	−14.6	−4.7	−62.4	38.3	−43.2
C6—H6⋯Cg(C1–C6)	−5.6	−1.5	−25.1	15.5	−16.7
C13—H13⋯Cg(C9–C14)	−8.9	−1.9	−30.9	14.2	−25.9
H11⋯C6	−5.0	−3.2	−50.6	24.7	−32.7
H8B⋯H8B	−5.0	−3.2	−50.6	24.7	−32.7

The significant contributions from the C—H⋯π inter­action and short inter­atomic C⋯H/H⋯C contacts in the crystal of (I) are evident from Table 5 ▸. Also notable, are the negligible energies associated with the Cl⋯Cl contacts due to the dominance of repulsive contributions. With respect to (II), it is evident from the comparison of the dispersive component as well as total energies for the different inter­actions that the strength of inter­actions in the crystal depend upon distance between the respective mol­ecules. The short Br⋯Br contacts in (II) also have very small inter­action energies.

The magnitudes of inter­molecular energies are represented graphically in the energy frameworks of Fig. 11 ▸. Here, the supra­molecular architecture of each crystal is viewed through the cylinders joining the centroids of mol­ecular pairs. The red (E _ele), green (E _disp) and blue (E _tot) colour scheme represent the specified energy components. The radii of the cylinders are proportional to the magnitude of inter­action energies which are adjusted with a cut-off value of 2 kJ mol⁻¹ within 4 × 4 × 4 unit cells. The energy frameworks constructed for the clusters about the independent mol­ecules A and B of (I) as well as that for (II) also indicate the distinct mode of supra­molecular association around the mol­ecules in the mol­ecular packing. The small effect of the electrostatic components and the significant influence of the dispersive components are clearly evident from the energy frameworks shown in Fig. 11 ▸.

Figure 11.

A comparison of the energy frameworks composed of (a) electrostatic potential force, (b) dispersion force and (c) total energy for cluster about a reference mol­ecule of A and B of (I), and for (II). The energy frameworks were adjusted to the same scale factor of 80 with a cut-off value of 2 kJ mol⁻¹ within 4 × 4 × 4 unit cells.

Database survey  

There are only four halo-substituted 1,2-bis­(phen­yl)ethyl­ene derivatives in the literature. The key structural parameters for these are summarized in Table 6 ▸. Only one literature structure is not disposed about a centre of inversion, namely the non-symmetric, mixed-halo structure (4-Br,2,6-F₂C₆H₂)CH₂CH₂C₆H₄Br-4 (Galán et al., 2016 ▸). Generally, the central C_e—C_e (e = ethyl­ene) bonds are long in these compounds with the exception being the penta­bromo derivative, C₆Br₅CH₂CH₂C₆Br₅ (Köppen et al., 2007 ▸).

Table 6. Geometric data (Å, °) for halo-substituted 1,2-bis­(phen­yl)ethane structures.

Ring 1	Ring 2	Symmetry	CH2—CH2	dihedral angle C6/C6	Reference
2-BrC6H4	2-BrC6H4		1.540 (7)	0	Kahr et al. (1995 ▸)
C6F5	C6F5		1.542 (3)	0	Krafczyk et al. (1997 ▸)
C6Br5	C6Br5		1.495 (13)	0	Köppen et al. (2007 ▸)
4-Br,2,6-F2C6H2	4-BrC6H4	–	1.522 (10)	1.67 (16)	Galán et al. (2016 ▸)
4-ClC6H4 a	4-ClC6H4		1.530 (2)	0	This work
			1.530 (3)	0
4-BrC6H4	4-BrC6H4	–	1.516 (3)	59.29 (11)	This work

Notes: (a) Two independent mol­ecules comprise the asymmetric unit.

Synthesis and crystallization  

Tri(4-chloro­benz­yl)tin chloride was prepared by direct synthesis using tin powder (Merck) and 4-chloro­benzyl chloride (Sigma–Aldrich) in water (Sisido et al., 1961 ▸). Tri(4-chloro­benz­yl)tin chloride (5.3 g, 10 mmol) was dissolved in 95% ethanol (150 ml) and to this was added dropwise 10% sodium hydroxide solution (4 ml). The resulting solution was heated for 1 h. After cooling, the white tri(4-chloro­benz­yl)tin hydroxide was filtered off and the filtrate was evaporated slowly to obtain a colourless crystalline solid which was identified crystallographically as (I). Yield: 0.28 g (0.11%). The bromo analogue was similarly obtained as a side-product from the base hydrolysis of tri(4-bromo­benz­yl)tin bromide. Tri(4-bromo­benzyl­tin) bromide was prepared from the reaction of tin powder (Sigma–Aldrich) and 4-bromo­benzyl bromide (Merck) in water (Sisido et al., 1961 ▸). Tri(4-bromo­benz­yl)tin bromide (7.0 g, 10 mmol) was dissolved in 95% ethanol (150 ml) and to this was added 10% sodium hydroxide solution (4 ml). The resulting precipitation was heated for 1 h. After cooling, the yellow tri(4-bromo­benz­yl)tin hydroxide was filtered off and the filtrate was evaporated slowly to obtain a yellow crystalline solid which was identified crystallographically as (II). Yield: 0.25 g (0.07%)

Refinement  

Crystal data, data collection and structure refinement details are summarized in Table 7 ▸. The carbon-bound H atoms were placed in calculated positions (C—H = 0.93–0.99 Å) and were included in the refinement in the riding-model approximation, with U _iso(H) set to 1.2U _eq(C). In the refinement of (II), owing to poor agreement the (111) reflection was omitted from the final cycles of refinement.

Table 7. Experimental details.

	(I)	(II)
Crystal data
Chemical formula	C14H12Cl2	C14H12Br2
M r	251.14	340.06
Crystal system, space group	Monoclinic, C2/c	Monoclinic, P21/c
Temperature (K)	296	100
a, b, c (Å)	26.6755 (19), 9.3259 (7), 10.0405 (8)	10.8761 (2), 7.5157 (1), 15.6131 (3)
β (°)	99.560 (4)	106.177 (1)
V (Å3)	2463.1 (3)	1225.71 (4)
Z	8	4
Radiation type	Mo Kα	Mo Kα
μ (mm−1)	0.50	6.58
Crystal size (mm)	0.30 × 0.20 × 0.10	0.20 × 0.11 × 0.07
Data collection
Diffractometer	Bruker SMART APEX CCD area detector	Bruker SMART APEX CCD area detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996 ▸)	Multi-scan (SADABS; Sheldrick, 1996 ▸)
T min, T max	0.623, 0.746	0.546, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	12061, 3090, 2627	11908, 3065, 2520
R int	0.026	0.035
(sin θ/λ)max (Å−1)	0.669	0.669
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.033, 0.090, 1.04	0.026, 0.058, 1.03
No. of reflections	3090	3065
No. of parameters	145	145
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρmax, Δρmin (e Å−3)	0.31, −0.27	0.45, −0.41

Computer programs: APEX2 (Bruker, 2008 ▸), SAINT (Bruker, 2008 ▸), SHELXS97 (Sheldrick, 2008 ▸), SHELXL2018/3 (Sheldrick, 2015 ▸), ORTEP-3 for Windows (Farrugia, 2012 ▸), DIAMOND (Brandenburg, 2006 ▸), QMol (Gans & Shalloway, 2001 ▸) and publCIF (Westrip, 2010 ▸).

Supplementary Material

CCDC references: 1908484, 1908483

Additional supporting information: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

1-Chloro-4-[2-(4-chlorophenyl)ethyl]benzene (I). Crystal data

C14H12Cl2	F(000) = 1040
Mr = 251.14	Dx = 1.354 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 26.6755 (19) Å	Cell parameters from 4470 reflections
b = 9.3259 (7) Å	θ = 3.1–28.3°
c = 10.0405 (8) Å	µ = 0.50 mm−1
β = 99.560 (4)°	T = 296 K
V = 2463.1 (3) Å3	Prism, colourless
Z = 8	0.30 × 0.20 × 0.10 mm

1-Chloro-4-[2-(4-chlorophenyl)ethyl]benzene (I). Data collection

Bruker model? CCD area detector diffractometer	3090 independent reflections
Radiation source: fine-focus sealed tube	2627 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 28.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −35→34
Tmin = 0.623, Tmax = 0.746	k = −11→12
12061 measured reflections	l = −13→13

1-Chloro-4-[2-(4-chlorophenyl)ethyl]benzene (I). Refinement

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.046P)2 + 1.4907P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3090 reflections	Δρmax = 0.31 e Å−3
145 parameters	Δρmin = −0.27 e Å−3
0 restraints

1-Chloro-4-[2-(4-chlorophenyl)ethyl]benzene (I). Special details

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.

1-Chloro-4-[2-(4-chlorophenyl)ethyl]benzene (I). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1A	0.30558 (2)	0.69571 (4)	0.08421 (3)	0.02990 (11)
C1A	0.35616 (5)	0.64904 (15)	0.20984 (13)	0.0213 (3)
C2A	0.39856 (5)	0.73741 (15)	0.23346 (13)	0.0227 (3)
H2A	0.400392	0.819329	0.181667	0.027*
C3A	0.43825 (5)	0.70121 (14)	0.33594 (13)	0.0224 (3)
H3A	0.466935	0.759394	0.351988	0.027*
C4A	0.43591 (5)	0.57952 (14)	0.41510 (13)	0.0202 (3)
C5A	0.39306 (5)	0.49193 (14)	0.38683 (13)	0.0224 (3)
H5A	0.391223	0.409246	0.437578	0.027*
C6A	0.35314 (5)	0.52569 (15)	0.28454 (13)	0.0237 (3)
H6A	0.324808	0.466334	0.266505	0.028*
C7A	0.47884 (5)	0.54105 (15)	0.52636 (13)	0.0236 (3)
H7A1	0.465754	0.482765	0.592893	0.028*
H7A2	0.492801	0.628077	0.570743	0.028*
Cl1B	0.44971 (2)	0.90465 (4)	0.91449 (4)	0.03360 (12)
C1B	0.39561 (5)	0.87925 (14)	0.79317 (14)	0.0229 (3)
C2B	0.34836 (6)	0.90808 (15)	0.82606 (14)	0.0271 (3)
H2B	0.345284	0.938736	0.912478	0.033*
C3B	0.30571 (5)	0.89060 (15)	0.72836 (15)	0.0274 (3)
H3B	0.273843	0.910620	0.749858	0.033*
C4B	0.30929 (5)	0.84387 (14)	0.59888 (13)	0.0223 (3)
C5B	0.35742 (5)	0.81356 (15)	0.56992 (14)	0.0254 (3)
H5B	0.360595	0.780451	0.484341	0.031*
C6B	0.40064 (5)	0.83161 (15)	0.66564 (14)	0.0258 (3)
H6B	0.432599	0.811998	0.644554	0.031*
C7B	0.26239 (5)	0.82320 (15)	0.49401 (15)	0.0272 (3)
H7B1	0.271471	0.832325	0.404772	0.033*
H7B2	0.238029	0.898025	0.504017	0.033*

1-Chloro-4-[2-(4-chlorophenyl)ethyl]benzene (I). Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Cl1A	0.02150 (17)	0.0400 (2)	0.02582 (18)	0.00466 (13)	−0.00301 (12)	0.00464 (14)
C1A	0.0173 (6)	0.0266 (7)	0.0191 (6)	0.0037 (5)	0.0005 (5)	−0.0009 (5)
C2A	0.0226 (6)	0.0237 (6)	0.0222 (6)	0.0005 (5)	0.0051 (5)	0.0011 (5)
C3A	0.0186 (6)	0.0257 (6)	0.0230 (6)	−0.0014 (5)	0.0041 (5)	−0.0029 (5)
C4A	0.0175 (6)	0.0246 (6)	0.0186 (6)	0.0046 (5)	0.0031 (5)	−0.0031 (5)
C5A	0.0230 (6)	0.0206 (6)	0.0236 (6)	0.0016 (5)	0.0035 (5)	0.0009 (5)
C6A	0.0199 (6)	0.0247 (7)	0.0258 (7)	−0.0028 (5)	0.0017 (5)	−0.0024 (5)
C7A	0.0199 (6)	0.0292 (7)	0.0207 (6)	0.0045 (5)	0.0003 (5)	−0.0019 (5)
Cl1B	0.02872 (19)	0.0322 (2)	0.0356 (2)	−0.00182 (13)	−0.00707 (15)	−0.00290 (14)
C1B	0.0223 (6)	0.0199 (6)	0.0251 (6)	−0.0016 (5)	0.0001 (5)	0.0008 (5)
C2B	0.0296 (7)	0.0296 (7)	0.0233 (7)	−0.0023 (5)	0.0076 (6)	−0.0057 (5)
C3B	0.0214 (6)	0.0308 (7)	0.0313 (7)	−0.0006 (5)	0.0084 (5)	−0.0031 (6)
C4B	0.0211 (6)	0.0203 (6)	0.0250 (6)	−0.0005 (5)	0.0024 (5)	0.0028 (5)
C5B	0.0279 (7)	0.0278 (7)	0.0215 (6)	0.0031 (5)	0.0067 (5)	−0.0011 (5)
C6B	0.0216 (6)	0.0280 (7)	0.0286 (7)	0.0041 (5)	0.0069 (5)	0.0002 (5)
C7B	0.0251 (7)	0.0269 (7)	0.0276 (7)	−0.0002 (5)	−0.0011 (6)	0.0033 (6)

1-Chloro-4-[2-(4-chlorophenyl)ethyl]benzene (I). Geometric parameters (Å, º)

Cl1A—C1A	1.7424 (13)	Cl1B—C1B	1.7432 (13)
C1A—C6A	1.3829 (19)	C1B—C2B	1.381 (2)
C1A—C2A	1.3877 (18)	C1B—C6B	1.383 (2)
C2A—C3A	1.3899 (18)	C2B—C3B	1.383 (2)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.3928 (19)	C3B—C4B	1.3895 (19)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.3952 (18)	C4B—C5B	1.3917 (18)
C4A—C7A	1.5043 (17)	C4B—C7B	1.5079 (18)
C5A—C6A	1.3873 (18)	C5B—C6B	1.3832 (19)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C7Ai	1.530 (2)	C7B—C7Bii	1.530 (3)
C7A—H7A1	0.9700	C7B—H7B1	0.9700
C7A—H7A2	0.9700	C7B—H7B2	0.9700
C6A—C1A—C2A	121.37 (12)	C2B—C1B—C6B	121.11 (12)
C6A—C1A—Cl1A	119.51 (10)	C2B—C1B—Cl1B	119.26 (11)
C2A—C1A—Cl1A	119.12 (10)	C6B—C1B—Cl1B	119.63 (10)
C1A—C2A—C3A	118.77 (12)	C3B—C2B—C1B	118.90 (13)
C1A—C2A—H2A	120.6	C3B—C2B—H2B	120.6
C3A—C2A—H2A	120.6	C1B—C2B—H2B	120.6
C2A—C3A—C4A	121.30 (12)	C2B—C3B—C4B	121.62 (13)
C2A—C3A—H3A	119.4	C2B—C3B—H3B	119.2
C4A—C3A—H3A	119.4	C4B—C3B—H3B	119.2
C3A—C4A—C5A	118.28 (12)	C3B—C4B—C5B	117.94 (12)
C3A—C4A—C7A	121.15 (12)	C3B—C4B—C7B	121.02 (12)
C5A—C4A—C7A	120.55 (12)	C5B—C4B—C7B	121.03 (12)
C6A—C5A—C4A	121.33 (12)	C6B—C5B—C4B	121.43 (13)
C6A—C5A—H5A	119.3	C6B—C5B—H5B	119.3
C4A—C5A—H5A	119.3	C4B—C5B—H5B	119.3
C5A—C6A—C1A	118.92 (12)	C5B—C6B—C1B	118.99 (12)
C5A—C6A—H6A	120.5	C5B—C6B—H6B	120.5
C1A—C6A—H6A	120.5	C1B—C6B—H6B	120.5
C4A—C7A—C7Ai	112.14 (13)	C4B—C7B—C7Bii	112.23 (14)
C4A—C7A—H7A1	109.2	C4B—C7B—H7B1	109.2
C7Ai—C7A—H7A1	109.2	C7Bii—C7B—H7B1	109.2
C4A—C7A—H7A2	109.2	C4B—C7B—H7B2	109.2
C7Ai—C7A—H7A2	109.2	C7Bii—C7B—H7B2	109.2
H7A1—C7A—H7A2	107.9	H7B1—C7B—H7B2	107.9
C6A—C1A—C2A—C3A	−0.98 (19)	C6B—C1B—C2B—C3B	−1.0 (2)
Cl1A—C1A—C2A—C3A	178.52 (10)	Cl1B—C1B—C2B—C3B	178.62 (11)
C1A—C2A—C3A—C4A	−0.5 (2)	C1B—C2B—C3B—C4B	0.5 (2)
C2A—C3A—C4A—C5A	1.63 (19)	C2B—C3B—C4B—C5B	0.5 (2)
C2A—C3A—C4A—C7A	−179.71 (12)	C2B—C3B—C4B—C7B	179.08 (13)
C3A—C4A—C5A—C6A	−1.28 (19)	C3B—C4B—C5B—C6B	−1.2 (2)
C7A—C4A—C5A—C6A	−179.95 (12)	C7B—C4B—C5B—C6B	−179.72 (13)
C4A—C5A—C6A—C1A	−0.2 (2)	C4B—C5B—C6B—C1B	0.8 (2)
C2A—C1A—C6A—C5A	1.3 (2)	C2B—C1B—C6B—C5B	0.3 (2)
Cl1A—C1A—C6A—C5A	−178.18 (10)	Cl1B—C1B—C6B—C5B	−179.24 (11)
C3A—C4A—C7A—C7Ai	−83.46 (19)	C3B—C4B—C7B—C7Bii	−83.7 (2)
C5A—C4A—C7A—C7Ai	95.17 (17)	C5B—C4B—C7B—C7Bii	94.75 (19)

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

1-Chloro-4-[2-(4-chlorophenyl)ethyl]benzene (I). Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the (C1A–C6A) ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5B—H5B···Cg1	0.93	2.62	3.4866 (15)	155

1-Bromo-4-[2-(4-chlorophenyl)ethyl]benzene (II). Crystal data

C14H12Br2	F(000) = 664
Mr = 340.06	Dx = 1.843 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.8761 (2) Å	Cell parameters from 3449 reflections
b = 7.5157 (1) Å	θ = 2.9–28.3°
c = 15.6131 (3) Å	µ = 6.58 mm−1
β = 106.177 (1)°	T = 100 K
V = 1225.71 (4) Å3	Prism, colourless
Z = 4	0.20 × 0.11 × 0.07 mm

1-Bromo-4-[2-(4-chlorophenyl)ethyl]benzene (II). Data collection

Bruker model? CCD area detector diffractometer	3065 independent reflections
Radiation source: fine-focus sealed tube	2520 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 28.4°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.546, Tmax = 0.746	k = −10→9
11908 measured reflections	l = −20→20

1-Bromo-4-[2-(4-chlorophenyl)ethyl]benzene (II). Refinement

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026	H-atom parameters constrained
wR(F2) = 0.058	w = 1/[σ2(Fo2) + (0.0289P)2 + 0.0779P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3065 reflections	Δρmax = 0.45 e Å−3
145 parameters	Δρmin = −0.40 e Å−3
0 restraints

1-Bromo-4-[2-(4-chlorophenyl)ethyl]benzene (II). Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Owing to poor agreement, the (1 1 1) reflection was omitted from the final cycles of refinement.

1-Bromo-4-[2-(4-chlorophenyl)ethyl]benzene (II). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.50841 (2)	0.84764 (3)	0.90903 (2)	0.02370 (8)
Br2	−0.25048 (2)	0.70383 (3)	0.09773 (2)	0.02253 (8)
C1	0.4150 (2)	0.8055 (3)	0.78827 (15)	0.0159 (5)
C2	0.3013 (2)	0.7135 (3)	0.77050 (15)	0.0161 (4)
H2	0.269796	0.672242	0.817887	0.019*
C3	0.2335 (2)	0.6817 (3)	0.68274 (15)	0.0177 (5)
H3	0.155194	0.617644	0.670292	0.021*
C4	0.2778 (2)	0.7417 (3)	0.61232 (15)	0.0167 (5)
C5	0.3933 (2)	0.8356 (3)	0.63289 (16)	0.0187 (5)
H5	0.425069	0.878319	0.585874	0.022*
C6	0.4624 (2)	0.8674 (3)	0.72041 (15)	0.0173 (5)
H6	0.541066	0.930801	0.733576	0.021*
C7	0.2051 (2)	0.7034 (4)	0.51691 (16)	0.0255 (6)
H7A	0.218424	0.577129	0.503799	0.031*
H7B	0.241041	0.777365	0.477256	0.031*
C8	0.0625 (2)	0.7386 (3)	0.49531 (15)	0.0212 (5)
H8A	0.025232	0.652822	0.529264	0.025*
H8B	0.049949	0.859257	0.516862	0.025*
C9	−0.0116 (2)	0.7260 (3)	0.39829 (14)	0.0147 (4)
C10	−0.1344 (2)	0.7992 (3)	0.36922 (15)	0.0167 (5)
H10	−0.170004	0.854105	0.411688	0.020*
C11	−0.2056 (2)	0.7945 (3)	0.28122 (15)	0.0172 (5)
H11	−0.288380	0.846752	0.263034	0.021*
C12	−0.1540 (2)	0.7119 (3)	0.21965 (15)	0.0161 (4)
C13	−0.0336 (2)	0.6354 (3)	0.24522 (15)	0.0172 (5)
H13	0.000460	0.578442	0.202509	0.021*
C14	0.0369 (2)	0.6430 (3)	0.33433 (15)	0.0154 (4)
H14	0.119669	0.590830	0.352166	0.018*

1-Bromo-4-[2-(4-chlorophenyl)ethyl]benzene (II). Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Br1	0.02109 (13)	0.02960 (15)	0.01712 (13)	−0.00317 (9)	−0.00014 (9)	−0.00484 (9)
Br2	0.01971 (13)	0.03068 (15)	0.01471 (12)	−0.00164 (9)	0.00065 (9)	0.00265 (9)
C1	0.0149 (11)	0.0157 (12)	0.0151 (11)	0.0040 (8)	0.0009 (9)	−0.0027 (8)
C2	0.0160 (11)	0.0163 (11)	0.0175 (11)	0.0019 (8)	0.0073 (9)	0.0018 (9)
C3	0.0136 (11)	0.0205 (12)	0.0185 (12)	−0.0004 (8)	0.0036 (9)	−0.0009 (9)
C4	0.0146 (11)	0.0200 (12)	0.0152 (11)	0.0023 (8)	0.0036 (9)	−0.0006 (9)
C5	0.0146 (11)	0.0216 (12)	0.0214 (12)	0.0015 (9)	0.0076 (9)	0.0038 (9)
C6	0.0106 (10)	0.0172 (12)	0.0243 (12)	−0.0004 (8)	0.0053 (9)	−0.0012 (9)
C7	0.0160 (12)	0.0436 (16)	0.0171 (12)	0.0027 (10)	0.0050 (10)	−0.0026 (11)
C8	0.0166 (12)	0.0281 (13)	0.0172 (12)	0.0018 (10)	0.0021 (9)	−0.0023 (10)
C9	0.0169 (11)	0.0132 (11)	0.0146 (11)	−0.0018 (8)	0.0054 (9)	0.0007 (8)
C10	0.0173 (11)	0.0152 (12)	0.0195 (12)	−0.0002 (8)	0.0082 (9)	0.0003 (9)
C11	0.0129 (10)	0.0172 (12)	0.0211 (12)	0.0006 (8)	0.0039 (9)	0.0026 (9)
C12	0.0160 (11)	0.0175 (12)	0.0133 (10)	−0.0038 (8)	0.0015 (9)	0.0025 (9)
C13	0.0189 (11)	0.0165 (12)	0.0174 (11)	−0.0011 (9)	0.0070 (9)	−0.0003 (9)
C14	0.0129 (11)	0.0160 (11)	0.0176 (11)	−0.0012 (8)	0.0048 (9)	0.0015 (9)

1-Bromo-4-[2-(4-chlorophenyl)ethyl]benzene (II). Geometric parameters (Å, º)

Br1—C1	1.902 (2)	C7—H7B	0.9900
Br2—C12	1.901 (2)	C8—C9	1.507 (3)
C1—C2	1.376 (3)	C8—H8A	0.9900
C1—C6	1.382 (3)	C8—H8B	0.9900
C2—C3	1.384 (3)	C9—C10	1.399 (3)
C2—H2	0.9500	C9—C14	1.399 (3)
C3—C4	1.393 (3)	C10—C11	1.377 (3)
C3—H3	0.9500	C10—H10	0.9500
C4—C5	1.398 (3)	C11—C12	1.388 (3)
C4—C7	1.507 (3)	C11—H11	0.9500
C5—C6	1.385 (3)	C12—C13	1.384 (3)
C5—H5	0.9500	C13—C14	1.390 (3)
C6—H6	0.9500	C13—H13	0.9500
C7—C8	1.516 (3)	C14—H14	0.9500
C7—H7A	0.9900
C2—C1—C6	121.4 (2)	C9—C8—C7	116.1 (2)
C2—C1—Br1	119.02 (17)	C9—C8—H8A	108.3
C6—C1—Br1	119.57 (17)	C7—C8—H8A	108.3
C1—C2—C3	119.2 (2)	C9—C8—H8B	108.3
C1—C2—H2	120.4	C7—C8—H8B	108.3
C3—C2—H2	120.4	H8A—C8—H8B	107.4
C2—C3—C4	121.3 (2)	C10—C9—C14	117.4 (2)
C2—C3—H3	119.4	C10—C9—C8	119.73 (19)
C4—C3—H3	119.4	C14—C9—C8	122.9 (2)
C3—C4—C5	117.9 (2)	C11—C10—C9	122.3 (2)
C3—C4—C7	121.1 (2)	C11—C10—H10	118.8
C5—C4—C7	120.9 (2)	C9—C10—H10	118.8
C6—C5—C4	121.3 (2)	C10—C11—C12	118.6 (2)
C6—C5—H5	119.3	C10—C11—H11	120.7
C4—C5—H5	119.3	C12—C11—H11	120.7
C1—C6—C5	118.8 (2)	C13—C12—C11	121.3 (2)
C1—C6—H6	120.6	C13—C12—Br2	119.32 (17)
C5—C6—H6	120.6	C11—C12—Br2	119.41 (17)
C4—C7—C8	114.2 (2)	C12—C13—C14	119.0 (2)
C4—C7—H7A	108.7	C12—C13—H13	120.5
C8—C7—H7A	108.7	C14—C13—H13	120.5
C4—C7—H7B	108.7	C13—C14—C9	121.4 (2)
C8—C7—H7B	108.7	C13—C14—H14	119.3
H7A—C7—H7B	107.6	C9—C14—H14	119.3
C6—C1—C2—C3	0.3 (3)	C7—C8—C9—C10	−163.7 (2)
Br1—C1—C2—C3	−179.64 (16)	C7—C8—C9—C14	16.4 (3)
C1—C2—C3—C4	−0.3 (3)	C14—C9—C10—C11	−1.3 (3)
C2—C3—C4—C5	0.0 (3)	C8—C9—C10—C11	178.8 (2)
C2—C3—C4—C7	178.7 (2)	C9—C10—C11—C12	0.9 (3)
C3—C4—C5—C6	0.4 (3)	C10—C11—C12—C13	0.0 (3)
C7—C4—C5—C6	−178.3 (2)	C10—C11—C12—Br2	−179.99 (16)
C2—C1—C6—C5	0.0 (3)	C11—C12—C13—C14	−0.5 (3)
Br1—C1—C6—C5	179.96 (16)	Br2—C12—C13—C14	179.49 (16)
C4—C5—C6—C1	−0.4 (3)	C12—C13—C14—C9	0.1 (3)
C3—C4—C7—C8	46.6 (3)	C10—C9—C14—C13	0.7 (3)
C5—C4—C7—C8	−134.8 (2)	C8—C9—C14—C13	−179.4 (2)
C4—C7—C8—C9	172.1 (2)

1-Bromo-4-[2-(4-chlorophenyl)ethyl]benzene (II). Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the (C1–C6) and (C9–C14) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg2i	0.95	2.69	3.442 (2)	136
C6—H6···Cg1ii	0.95	2.91	3.704 (2)	141
C13—H13···Cg2iii	0.95	2.87	3.569 (2)	131

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