2-Bromo-p-terphen-yl.

In the title compound, C(18)H(13)Br, the dihedral angles between the mean planes of the central benzene ring and the mean planes of the outer phenyl and bromo-phenyl rings are 33.47 (8) and 66.35 (8)°, respectively. In the crystal, weak C-H⋯π and inter-molecular Br⋯Br [3.5503 (15) Å] inter-actions contribute to the stabilization of the packing.

Related literature

For the synthesis, see: France et al. (1938 ▶); Tadashi et al. (1962 ▶). For the Suzuki coupling reaction, see: Miyaura & Suzuki (1995 ▶). For cross-coupling reactions of o-halogenated arenes, see: Ishikawa & Manabe (2007 ▶). For organic light-emitting diodes, see: Kim et al. (2008 ▶). For related structures, see: Jones et al. (2005 ▶); Liang (2008 ▶); MacNeil & Decken (1999 ▶); Politzer et al. (2007 ▶).

Experimental

Crystal data

C18H13Br

M = 309.19

Monoclinic,

a = 27.039 (10) Å

b = 7.597 (3) Å

c = 18.907 (7) Å

β = 133.650 (5)°

V = 2810 (2) Å3

Z = 8

Mo Kα radiation

μ = 2.91 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.476, T max = 0.594

13933 measured reflections

3503 independent reflections

2246 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.092

S = 1.02

3503 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.65 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810007348/jj2023sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007348/jj2023Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H13Br	F(000) = 1248
Mr = 309.19	Dx = 1.462 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3654 reflections
a = 27.039 (10) Å	θ = 2.1–28.4°
b = 7.597 (3) Å	µ = 2.91 mm−1
c = 18.907 (7) Å	T = 293 K
β = 133.650 (5)°	Block, colorless
V = 2810 (2) Å3	0.30 × 0.25 × 0.20 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	3503 independent reflections
Radiation source: fine-focus sealed tube	2246 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 28.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	h = −34→36
Tmin = 0.476, Tmax = 0.594	k = −9→10
13933 measured reflections	l = −25→25

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0341P)2 + 2.6031P] where P = (Fo2 + 2Fc2)/3
3503 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.65 e Å−3

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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.721104 (15)	0.25216 (4)	0.56047 (2)	0.07170 (13)
C1	0.69010 (12)	0.4341 (3)	0.59063 (16)	0.0458 (5)
C2	0.73645 (13)	0.5631 (3)	0.65377 (18)	0.0565 (6)
H2	0.7807	0.5590	0.6797	0.068*
C3	0.71685 (15)	0.6982 (3)	0.67834 (19)	0.0613 (7)
H3	0.7478	0.7861	0.7210	0.074*
C4	0.65143 (16)	0.7030 (3)	0.6398 (2)	0.0616 (7)
H4	0.6384	0.7930	0.6575	0.074*
C5	0.60498 (13)	0.5756 (3)	0.57514 (18)	0.0552 (6)
H5	0.5606	0.5819	0.5489	0.066*
C6	0.62281 (11)	0.4369 (3)	0.54788 (15)	0.0434 (5)
C7	0.57071 (12)	0.3039 (3)	0.47552 (17)	0.0446 (5)
C8	0.51546 (12)	0.3516 (3)	0.37957 (17)	0.0519 (6)
H8	0.5104	0.4684	0.3609	0.062*
C9	0.46779 (12)	0.2289 (3)	0.31111 (18)	0.0522 (6)
H9	0.4310	0.2648	0.2472	0.063*
C10	0.47356 (11)	0.0529 (3)	0.33573 (16)	0.0441 (5)
C11	0.52859 (12)	0.0067 (3)	0.43275 (16)	0.0520 (6)
H11	0.5334	−0.1097	0.4519	0.062*
C12	0.57609 (13)	0.1291 (3)	0.50101 (17)	0.0524 (6)
H12	0.6124	0.0940	0.5653	0.063*
C13	0.42539 (11)	−0.0832 (3)	0.26121 (16)	0.0453 (5)
C14	0.39663 (13)	−0.0664 (4)	0.16585 (18)	0.0592 (6)
H14	0.4062	0.0328	0.1483	0.071*
C15	0.35413 (16)	−0.1948 (4)	0.0972 (2)	0.0730 (8)
H15	0.3359	−0.1824	0.0340	0.088*
C16	0.33855 (14)	−0.3410 (4)	0.1214 (2)	0.0703 (8)
H16	0.3098	−0.4273	0.0749	0.084*
C17	0.36580 (13)	−0.3588 (3)	0.2151 (2)	0.0598 (7)
H17	0.3550	−0.4569	0.2316	0.072*
C18	0.40904 (13)	−0.2318 (3)	0.28455 (19)	0.0519 (6)
H18	0.4275	−0.2457	0.3477	0.062*

	U11	U22	U33	U12	U13	U23
Br1	0.0723 (2)	0.0729 (2)	0.0885 (2)	0.00301 (14)	0.0625 (2)	−0.01335 (15)
C1	0.0545 (14)	0.0446 (12)	0.0456 (13)	0.0024 (11)	0.0373 (12)	0.0014 (10)
C2	0.0533 (14)	0.0587 (15)	0.0542 (14)	−0.0045 (12)	0.0358 (13)	0.0008 (12)
C3	0.0735 (19)	0.0519 (14)	0.0538 (16)	−0.0128 (13)	0.0421 (15)	−0.0089 (12)
C4	0.085 (2)	0.0461 (14)	0.0686 (17)	0.0016 (13)	0.0585 (17)	−0.0044 (12)
C5	0.0604 (15)	0.0474 (14)	0.0635 (16)	0.0056 (12)	0.0449 (14)	0.0019 (12)
C6	0.0498 (13)	0.0417 (12)	0.0408 (12)	0.0028 (10)	0.0320 (11)	0.0049 (9)
C7	0.0478 (13)	0.0444 (12)	0.0457 (13)	0.0023 (10)	0.0338 (12)	0.0007 (10)
C8	0.0521 (14)	0.0397 (13)	0.0531 (15)	0.0063 (11)	0.0322 (13)	0.0065 (11)
C9	0.0461 (13)	0.0519 (15)	0.0438 (13)	0.0079 (11)	0.0254 (11)	0.0078 (11)
C10	0.0424 (12)	0.0472 (12)	0.0451 (12)	0.0016 (10)	0.0312 (11)	0.0007 (10)
C11	0.0570 (15)	0.0439 (13)	0.0462 (14)	0.0000 (11)	0.0323 (13)	0.0063 (11)
C12	0.0528 (14)	0.0498 (14)	0.0406 (12)	−0.0006 (11)	0.0270 (12)	0.0044 (11)
C13	0.0404 (12)	0.0480 (13)	0.0467 (13)	0.0030 (10)	0.0298 (11)	0.0010 (10)
C14	0.0581 (15)	0.0671 (17)	0.0520 (15)	−0.0102 (13)	0.0378 (13)	−0.0029 (13)
C15	0.0733 (19)	0.085 (2)	0.0504 (16)	−0.0171 (16)	0.0388 (16)	−0.0123 (15)
C16	0.0628 (18)	0.0634 (18)	0.0646 (19)	−0.0129 (14)	0.0363 (16)	−0.0165 (14)
C17	0.0541 (15)	0.0479 (14)	0.0654 (17)	−0.0005 (12)	0.0367 (14)	0.0014 (13)
C18	0.0493 (13)	0.0500 (14)	0.0504 (14)	0.0041 (11)	0.0322 (12)	0.0047 (11)

Br1—C1	1.897 (2)	C9—H9	0.9300
C1—C2	1.375 (3)	C10—C11	1.391 (3)
C1—C6	1.391 (3)	C10—C13	1.489 (3)
C2—C3	1.375 (4)	C11—C12	1.376 (3)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.372 (4)	C12—H12	0.9300
C3—H3	0.9300	C13—C18	1.390 (3)
C4—C5	1.374 (4)	C13—C14	1.391 (3)
C4—H4	0.9300	C14—C15	1.378 (4)
C5—C6	1.397 (3)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.374 (4)
C6—C7	1.489 (3)	C15—H15	0.9300
C7—C8	1.383 (3)	C16—C17	1.377 (4)
C7—C12	1.386 (3)	C16—H16	0.9300
C8—C9	1.379 (3)	C17—C18	1.380 (3)
C8—H8	0.9300	C17—H17	0.9300
C9—C10	1.389 (3)	C18—H18	0.9300
C2—C1—C6	122.4 (2)	C9—C10—C11	117.1 (2)
C2—C1—Br1	116.95 (18)	C9—C10—C13	121.9 (2)
C6—C1—Br1	120.61 (17)	C11—C10—C13	120.9 (2)
C3—C2—C1	119.5 (2)	C12—C11—C10	121.5 (2)
C3—C2—H2	120.2	C12—C11—H11	119.2
C1—C2—H2	120.2	C10—C11—H11	119.2
C4—C3—C2	119.8 (2)	C11—C12—C7	121.1 (2)
C4—C3—H3	120.1	C11—C12—H12	119.5
C2—C3—H3	120.1	C7—C12—H12	119.5
C3—C4—C5	120.4 (2)	C18—C13—C14	118.1 (2)
C3—C4—H4	119.8	C18—C13—C10	121.7 (2)
C5—C4—H4	119.8	C14—C13—C10	120.2 (2)
C4—C5—C6	121.5 (2)	C15—C14—C13	120.8 (3)
C4—C5—H5	119.2	C15—C14—H14	119.6
C6—C5—H5	119.2	C13—C14—H14	119.6
C1—C6—C5	116.3 (2)	C16—C15—C14	120.4 (3)
C1—C6—C7	123.5 (2)	C16—C15—H15	119.8
C5—C6—C7	120.2 (2)	C14—C15—H15	119.8
C8—C7—C12	117.8 (2)	C15—C16—C17	119.6 (3)
C8—C7—C6	120.5 (2)	C15—C16—H16	120.2
C12—C7—C6	121.7 (2)	C17—C16—H16	120.2
C9—C8—C7	121.2 (2)	C16—C17—C18	120.4 (3)
C9—C8—H8	119.4	C16—C17—H17	119.8
C7—C8—H8	119.4	C18—C17—H17	119.8
C8—C9—C10	121.3 (2)	C17—C18—C13	120.8 (2)
C8—C9—H9	119.3	C17—C18—H18	119.6
C10—C9—H9	119.3	C13—C18—H18	119.6
C6—C1—C2—C3	1.8 (4)	C8—C9—C10—C13	−175.5 (2)
Br1—C1—C2—C3	−179.94 (19)	C9—C10—C11—C12	−1.3 (3)
C1—C2—C3—C4	0.0 (4)	C13—C10—C11—C12	175.5 (2)
C2—C3—C4—C5	−1.4 (4)	C10—C11—C12—C7	0.2 (4)
C3—C4—C5—C6	1.0 (4)	C8—C7—C12—C11	1.0 (4)
C2—C1—C6—C5	−2.2 (3)	C6—C7—C12—C11	−178.2 (2)
Br1—C1—C6—C5	179.65 (16)	C9—C10—C13—C18	−149.7 (2)
C2—C1—C6—C7	176.8 (2)	C11—C10—C13—C18	33.6 (3)
Br1—C1—C6—C7	−1.4 (3)	C9—C10—C13—C14	31.9 (3)
C4—C5—C6—C1	0.8 (3)	C11—C10—C13—C14	−144.8 (2)
C4—C5—C6—C7	−178.2 (2)	C18—C13—C14—C15	−1.1 (4)
C1—C6—C7—C8	−113.1 (3)	C10—C13—C14—C15	177.4 (3)
C5—C6—C7—C8	65.9 (3)	C13—C14—C15—C16	1.0 (5)
C1—C6—C7—C12	66.1 (3)	C14—C15—C16—C17	−0.1 (5)
C5—C6—C7—C12	−115.0 (3)	C15—C16—C17—C18	−0.7 (4)
C12—C7—C8—C9	−0.9 (4)	C16—C17—C18—C13	0.6 (4)
C6—C7—C8—C9	178.2 (2)	C14—C13—C18—C17	0.3 (3)
C7—C8—C9—C10	−0.3 (4)	C10—C13—C18—C17	−178.2 (2)
C8—C9—C10—C11	1.4 (4)

Cg2 and Cg3 are the centroids of the C7–C12 and C13–C18 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg3i	0.93	2.84	3.778 (4)	148
C14—H14···Cg2ii	0.93	2.97	3.658 (5)	147

Table 1

C—H⋯π inter­actions (Å, °)

Cg2 and Cg3 are the centroids of the C7–C12 and C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg3i	0.93	2.84	3.778 (4)	148
C14—H14⋯Cg2ii	0.93	2.97	3.658 (5)	147

Symmetry codes: (i) ; (ii) .