4-(4-Bromo-phen-yl)-2,6-diphenyl-pyridine.

In the title compound, C(23)H(16)BrN, the three benzene rings show a disrotatory counter-rotating arrangement around the central pyridine ring and are twisted with respect to the pyridine ring with dihedral angles of 19.56 (13), 27.54 (13) and 30.51 (13)°.

Related literature

For applications of the title compound, see: Verma et al. (2007 ▶); Vellis et al. (2008 ▶). For related structures, see: Lv & Huang (2008 ▶); Ondrá˘cek et al. (1994 ▶). For the synthesis, see: Verma et al. (2007 ▶).

Experimental

Crystal data

C23H16BrN

M = 386.28

Monoclinic,

a = 8.9837 (4) Å

b = 21.5202 (10) Å

c = 9.6108 (4) Å

β = 105.5940 (10)°

V = 1789.67 (14) Å3

Z = 4

Mo Kα radiation

μ = 2.30 mm−1

T = 293 K

0.30 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.542, T max = 0.652

13423 measured reflections

4325 independent reflections

2433 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.105

S = 1.01

4325 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.43 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049253/xu2640sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049253/xu2640Isup2.hkl

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

C23H16BrN	F(000) = 784
Mr = 386.28	Dx = 1.434 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 987 reflections
a = 8.9837 (4) Å	θ = 2.9–25.1°
b = 21.5202 (10) Å	µ = 2.30 mm−1
c = 9.6108 (4) Å	T = 293 K
β = 105.594 (1)°	Block, colorless
V = 1789.67 (14) Å3	0.30 × 0.22 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	4325 independent reflections
Radiation source: fine-focus sealed tube	2433 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.542, Tmax = 0.652	k = −28→27
13423 measured reflections	l = −11→12

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0449P)2 + 0.3089P] where P = (Fo2 + 2Fc2)/3
4325 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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	0.28459 (4)	0.440827 (13)	0.83895 (4)	0.08918 (16)
N1	−0.0501 (2)	0.82145 (8)	0.9831 (2)	0.0538 (5)
C7	−0.1196 (2)	0.76960 (11)	1.0130 (2)	0.0518 (6)
C12	0.1459 (2)	0.87312 (11)	0.8977 (3)	0.0530 (6)
C21	0.2129 (3)	0.52227 (11)	0.8610 (3)	0.0597 (6)
C23	0.2619 (3)	0.62976 (12)	0.9073 (3)	0.0599 (6)
H23A	0.3310	0.6628	0.9268	0.072*
C16	0.2240 (3)	0.97801 (12)	0.9653 (3)	0.0733 (7)
H16A	0.2220	1.0125	1.0230	0.088*
C9	0.0510 (3)	0.70294 (10)	0.9250 (3)	0.0527 (6)
C11	0.0680 (3)	0.81496 (10)	0.9238 (3)	0.0527 (6)
C10	0.1200 (3)	0.75706 (11)	0.8935 (3)	0.0570 (6)
H10A	0.2019	0.7545	0.8517	0.068*
C8	−0.0713 (3)	0.71067 (10)	0.9864 (3)	0.0556 (6)
H8A	−0.1212	0.6759	1.0098	0.067*
C19	0.0068 (3)	0.59007 (11)	0.8679 (3)	0.0617 (6)
H19A	−0.0978	0.5962	0.8591	0.074*
C18	0.1063 (3)	0.64034 (10)	0.8985 (3)	0.0526 (6)
C17	0.1437 (3)	0.92504 (11)	0.9818 (3)	0.0629 (7)
H17A	0.0876	0.9243	1.0502	0.076*
C15	0.3066 (3)	0.98002 (13)	0.8645 (3)	0.0718 (8)
H15A	0.3629	1.0154	0.8555	0.086*
C13	0.2264 (3)	0.87648 (12)	0.7932 (3)	0.0620 (6)
H13A	0.2266	0.8425	0.7335	0.074*
C5	−0.3104 (3)	0.73186 (13)	1.1431 (3)	0.0683 (7)
H5A	−0.2590	0.6939	1.1585	0.082*
C20	0.0587 (3)	0.53108 (11)	0.8502 (3)	0.0628 (6)
H20A	−0.0096	0.4977	0.8313	0.075*
C6	−0.2546 (3)	0.77920 (11)	1.0728 (3)	0.0525 (6)
C1	−0.3309 (3)	0.83534 (12)	1.0563 (3)	0.0681 (7)
H1B	−0.2942	0.8681	1.0117	0.082*
C2	−0.4611 (3)	0.84380 (13)	1.1047 (3)	0.0772 (8)
H2A	−0.5110	0.8821	1.0926	0.093*
C14	0.3058 (3)	0.92962 (13)	0.7769 (3)	0.0716 (8)
H14A	0.3591	0.9313	0.7063	0.086*
C4	−0.4407 (3)	0.74032 (14)	1.1904 (3)	0.0748 (8)
H4A	−0.4774	0.7080	1.2361	0.090*
C22	0.3151 (3)	0.57114 (12)	0.8876 (3)	0.0640 (7)
H22A	0.4187	0.5648	0.8924	0.077*
C3	−0.5166 (3)	0.79637 (13)	1.1701 (3)	0.0731 (8)
H3A	−0.6054	0.8019	1.2009	0.088*

	U11	U22	U33	U12	U13	U23
Br1	0.0970 (3)	0.0623 (2)	0.1124 (3)	0.02012 (15)	0.0353 (2)	0.00041 (16)
N1	0.0535 (11)	0.0557 (11)	0.0563 (13)	−0.0001 (9)	0.0215 (9)	−0.0006 (9)
C7	0.0517 (13)	0.0565 (13)	0.0503 (15)	0.0016 (10)	0.0190 (11)	0.0046 (11)
C12	0.0506 (13)	0.0571 (14)	0.0539 (15)	−0.0012 (10)	0.0185 (11)	−0.0006 (11)
C21	0.0681 (16)	0.0547 (14)	0.0591 (16)	0.0088 (12)	0.0220 (13)	0.0018 (11)
C23	0.0553 (14)	0.0605 (15)	0.0697 (17)	−0.0020 (11)	0.0268 (13)	0.0006 (12)
C16	0.0888 (19)	0.0562 (15)	0.078 (2)	−0.0075 (14)	0.0275 (16)	−0.0077 (13)
C9	0.0499 (13)	0.0569 (13)	0.0530 (15)	−0.0002 (10)	0.0169 (11)	0.0002 (11)
C11	0.0538 (13)	0.0556 (13)	0.0518 (15)	−0.0034 (10)	0.0193 (11)	−0.0010 (11)
C10	0.0540 (14)	0.0617 (14)	0.0616 (16)	−0.0008 (11)	0.0264 (12)	−0.0023 (12)
C8	0.0550 (14)	0.0519 (13)	0.0642 (17)	−0.0024 (11)	0.0233 (12)	0.0033 (11)
C19	0.0509 (13)	0.0642 (15)	0.0719 (18)	0.0019 (12)	0.0199 (12)	−0.0034 (13)
C18	0.0546 (14)	0.0536 (13)	0.0534 (15)	0.0016 (11)	0.0211 (11)	0.0022 (11)
C17	0.0676 (15)	0.0623 (15)	0.0651 (18)	−0.0021 (12)	0.0283 (13)	−0.0044 (12)
C15	0.0720 (17)	0.0625 (16)	0.082 (2)	−0.0154 (13)	0.0233 (16)	0.0028 (14)
C13	0.0646 (15)	0.0619 (15)	0.0654 (17)	−0.0070 (12)	0.0276 (13)	−0.0063 (12)
C5	0.0726 (17)	0.0617 (15)	0.080 (2)	0.0029 (13)	0.0366 (15)	0.0087 (13)
C20	0.0646 (16)	0.0544 (14)	0.0713 (18)	−0.0029 (12)	0.0214 (13)	−0.0035 (12)
C6	0.0484 (13)	0.0567 (13)	0.0560 (15)	0.0003 (10)	0.0199 (11)	−0.0019 (11)
C1	0.0663 (16)	0.0598 (15)	0.088 (2)	0.0006 (12)	0.0375 (15)	0.0012 (14)
C2	0.0694 (17)	0.0671 (17)	0.106 (2)	0.0104 (13)	0.0426 (17)	−0.0017 (16)
C14	0.0718 (17)	0.0760 (18)	0.076 (2)	−0.0115 (13)	0.0353 (15)	0.0028 (15)
C4	0.0745 (18)	0.0799 (19)	0.083 (2)	−0.0101 (15)	0.0439 (16)	0.0053 (15)
C22	0.0567 (14)	0.0686 (17)	0.0702 (18)	0.0105 (12)	0.0231 (13)	0.0039 (13)
C3	0.0576 (16)	0.087 (2)	0.084 (2)	0.0001 (14)	0.0350 (15)	−0.0095 (16)

Br1—C21	1.899 (2)	C19—C20	1.379 (3)
N1—C11	1.340 (3)	C19—C18	1.383 (3)
N1—C7	1.347 (3)	C19—H19A	0.9300
C7—C8	1.386 (3)	C17—H17A	0.9300
C7—C6	1.490 (3)	C15—C14	1.372 (4)
C12—C17	1.382 (3)	C15—H15A	0.9300
C12—C13	1.389 (3)	C13—C14	1.379 (3)
C12—C11	1.488 (3)	C13—H13A	0.9300
C21—C20	1.374 (3)	C5—C4	1.377 (3)
C21—C22	1.374 (4)	C5—C6	1.388 (3)
C23—C22	1.380 (3)	C5—H5A	0.9300
C23—C18	1.397 (3)	C20—H20A	0.9300
C23—H23A	0.9300	C6—C1	1.377 (3)
C16—C15	1.371 (4)	C1—C2	1.383 (3)
C16—C17	1.381 (3)	C1—H1B	0.9300
C16—H16A	0.9300	C2—C3	1.362 (4)
C9—C8	1.390 (3)	C2—H2A	0.9300
C9—C10	1.390 (3)	C14—H14A	0.9300
C9—C18	1.481 (3)	C4—C3	1.374 (4)
C11—C10	1.389 (3)	C4—H4A	0.9300
C10—H10A	0.9300	C22—H22A	0.9300
C8—H8A	0.9300	C3—H3A	0.9300
C11—N1—C7	118.03 (19)	C16—C17—H17A	119.6
N1—C7—C8	122.17 (19)	C12—C17—H17A	119.6
N1—C7—C6	116.1 (2)	C16—C15—C14	119.6 (2)
C8—C7—C6	121.7 (2)	C16—C15—H15A	120.2
C17—C12—C13	118.2 (2)	C14—C15—H15A	120.2
C17—C12—C11	120.1 (2)	C14—C13—C12	120.8 (2)
C13—C12—C11	121.7 (2)	C14—C13—H13A	119.6
C20—C21—C22	121.2 (2)	C12—C13—H13A	119.6
C20—C21—Br1	118.97 (19)	C4—C5—C6	120.9 (3)
C22—C21—Br1	119.85 (19)	C4—C5—H5A	119.5
C22—C23—C18	121.2 (2)	C6—C5—H5A	119.5
C22—C23—H23A	119.4	C21—C20—C19	119.0 (2)
C18—C23—H23A	119.4	C21—C20—H20A	120.5
C15—C16—C17	120.4 (2)	C19—C20—H20A	120.5
C15—C16—H16A	119.8	C1—C6—C5	117.8 (2)
C17—C16—H16A	119.8	C1—C6—C7	120.6 (2)
C8—C9—C10	116.2 (2)	C5—C6—C7	121.6 (2)
C8—C9—C18	121.4 (2)	C6—C1—C2	121.1 (2)
C10—C9—C18	122.3 (2)	C6—C1—H1B	119.4
N1—C11—C10	122.1 (2)	C2—C1—H1B	119.4
N1—C11—C12	116.48 (19)	C3—C2—C1	120.3 (3)
C10—C11—C12	121.3 (2)	C3—C2—H2A	119.8
C11—C10—C9	120.8 (2)	C1—C2—H2A	119.8
C11—C10—H10A	119.6	C15—C14—C13	120.2 (3)
C9—C10—H10A	119.6	C15—C14—H14A	119.9
C7—C8—C9	120.7 (2)	C13—C14—H14A	119.9
C7—C8—H8A	119.7	C3—C4—C5	120.2 (3)
C9—C8—H8A	119.7	C3—C4—H4A	119.9
C20—C19—C18	121.7 (2)	C5—C4—H4A	119.9
C20—C19—H19A	119.1	C21—C22—C23	119.1 (2)
C18—C19—H19A	119.1	C21—C22—H22A	120.4
C19—C18—C23	117.7 (2)	C23—C22—H22A	120.4
C19—C18—C9	121.4 (2)	C2—C3—C4	119.6 (2)
C23—C18—C9	120.9 (2)	C2—C3—H3A	120.2
C16—C17—C12	120.7 (2)	C4—C3—H3A	120.2
C11—N1—C7—C8	1.0 (3)	C13—C12—C17—C16	−2.2 (4)
C11—N1—C7—C6	−177.4 (2)	C11—C12—C17—C16	175.7 (2)
C7—N1—C11—C10	−0.3 (4)	C17—C16—C15—C14	1.8 (4)
C7—N1—C11—C12	−177.6 (2)	C17—C12—C13—C14	2.0 (4)
C17—C12—C11—N1	26.4 (3)	C11—C12—C13—C14	−175.9 (2)
C13—C12—C11—N1	−155.7 (2)	C22—C21—C20—C19	−0.6 (4)
C17—C12—C11—C10	−150.9 (2)	Br1—C21—C20—C19	179.22 (19)
C13—C12—C11—C10	27.0 (4)	C18—C19—C20—C21	−1.1 (4)
N1—C11—C10—C9	−0.4 (4)	C4—C5—C6—C1	2.0 (4)
C12—C11—C10—C9	176.8 (2)	C4—C5—C6—C7	−176.2 (3)
C8—C9—C10—C11	0.4 (3)	N1—C7—C6—C1	19.2 (3)
C18—C9—C10—C11	−178.1 (2)	C8—C7—C6—C1	−159.2 (2)
N1—C7—C8—C9	−1.0 (4)	N1—C7—C6—C5	−162.6 (2)
C6—C7—C8—C9	177.3 (2)	C8—C7—C6—C5	19.0 (4)
C10—C9—C8—C7	0.2 (4)	C5—C6—C1—C2	−1.6 (4)
C18—C9—C8—C7	178.7 (2)	C7—C6—C1—C2	176.6 (3)
C20—C19—C18—C23	1.6 (4)	C6—C1—C2—C3	−0.1 (5)
C20—C19—C18—C9	−176.7 (2)	C16—C15—C14—C13	−2.0 (4)
C22—C23—C18—C19	−0.6 (4)	C12—C13—C14—C15	0.1 (4)
C22—C23—C18—C9	177.8 (2)	C6—C5—C4—C3	−0.8 (4)
C8—C9—C18—C19	30.6 (4)	C20—C21—C22—C23	1.6 (4)
C10—C9—C18—C19	−151.0 (2)	Br1—C21—C22—C23	−178.2 (2)
C8—C9—C18—C23	−147.7 (2)	C18—C23—C22—C21	−0.9 (4)
C10—C9—C18—C23	30.7 (3)	C1—C2—C3—C4	1.3 (5)
C15—C16—C17—C12	0.4 (4)	C5—C4—C3—C2	−0.9 (5)