4-(4-Bromo­phen­yl)-2,6-diphenyl­pyridine

Cao, Q.; Xie, Y.; Jia, J.; Hong, X.-W.

doi:10.1107/S1600536809049253

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3182

doi:10.1107/S1600536809049253

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4-(4-Bromophenyl)-2,6-diphenylpyridine

Qun Cao,^a Yu Xie,^a,^b ^* Jie Jia ^a and Xiao-Wei Hong ^a

^aKey Laboratory of Nondestructive Testing (Ministry of Education), Nanchang Hangkong University, Nanchang 330063, People's Republic of China, and ^bKey Laboratory of Photochemical Conversion and Optoelectronic Materials, TIPC, CAS, Beijing 100190, People's Republic of China
^*Correspondence e-mail: xieyu_121@163.com

(Received 15 October 2009; accepted 18 November 2009; online 21 November 2009)

In the title compound, C₂₃H₁₆BrN, 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_r = 386.28
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.105
S = 1.01
4325 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −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.

Supporting information

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

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

checkCIF report

Comment top

The title compound, 4-(4-bromophenyl)-2,6-diphenylpyridine (I), is an useful intermediate in the synthesis of electroluminescent materials or new supramolecules (Verma et al., 2007; Vellis et al., 2008). It has been synthesized previously. We reported its structure here.

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in reported the compound (Ondrá˘cek et al., 1994; Lv & Huang, 2008). The three phenyl rings display a disrotatory conformation and form different angles with the pyridine ring. The dihedral angles between the pyridine ring and the two phenyls in 2- and 6- position are 19.56 (13) and 27.54 (13) ° respectively, while the phenyl ring in 4- position forms the largest angle with the heterocycle, 30.51 (13)°.

Related literature top

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 top

The title compound was prepared by literature method (Verma et al., 2007). Colorless single crystals suitable for X-ray diffraction were obtained from the solution of dichloromethane by vapor diffusion with hexane.

Computing details top

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

Figures top

Fig. 1. : The molecular structure of compound (I). Displacement ellipsoids are drawn at the 30% probability level. The H atoms are omitted for clarity.

4-(4-Bromophenyl)-2,6-diphenylpyridine top

Crystal data top

C₂₃H₁₆BrN	F(000) = 784
M_r = 386.28	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0449P)² + 0.3089P] where P = (F_o² + 2F_c²)/3
4325 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₃H₁₆BrN	V = 1789.67 (14) Å³
M_r = 386.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.9837 (4) Å	µ = 2.30 mm⁻¹
b = 21.5202 (10) Å	T = 293 K
c = 9.6108 (4) Å	0.30 × 0.22 × 0.20 mm
β = 105.594 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4325 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2433 reflections with I > 2σ(I)
T_min = 0.542, T_max = 0.652	R_int = 0.027
13423 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.01	Δρ_max = 0.42 e Å⁻³
4325 reflections	Δρ_min = −0.43 e Å⁻³
226 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₃H₁₆BrN
M_r	386.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.9837 (4), 21.5202 (10), 9.6108 (4)
β (°)	105.594 (1)
V (Å³)	1789.67 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.30
Crystal size (mm)	0.30 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.542, 0.652
No. of measured, independent and observed [I > 2σ(I)] reflections	13423, 4325, 2433
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.105, 1.01
No. of reflections	4325
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.43

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank the Key Laboratory of Photochemical Conversion and Optoelectronic Materials, TIPC, CAS and Jiangxi Provincial Department of Education for financial support for this work. In addition, the Materials Chemistry Department of Nanchang Hangkong University is acknowleged.

References

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