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

In the title compound, C(23)H(16)ClN, the crystal packing exhibits no significantly short inter-molecular contacts. The benzene rings show a disrotatory arrangement and the angles between them and the pyridine ring range from 20.80 (3) to 37.56 (4)°. The Cl atom deviates by 0.01 (3) Å from the plane of the benzene ring to which it is attached.

Related literature

For the structure of 2,4,6-triphenyl­pyridine, see: Ondracek et al. (1994 ▶).

Experimental

Crystal data

C23H16ClN

M = 341.82

Monoclinic,

a = 9.3995 (11) Å

b = 20.621 (2) Å

c = 9.5362 (12) Å

β = 108.146 (2)°

V = 1756.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 298 (2) K

0.42 × 0.37 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.913, T max = 0.968

8674 measured reflections

3078 independent reflections

1752 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.135

S = 1.02

3078 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807064380/av2004sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064380/av2004Isup2.hkl

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

C23H16ClN	F000 = 712
Mr = 341.82	Dx = 1.293 Mg m−3
Monoclinic, P2(1)/c	Mo Kα radiation λ = 0.71073 Å
a = 9.3995 (11) Å	Cell parameters from 1970 reflections
b = 20.621 (2) Å	θ = 2.3–25.2º
c = 9.5362 (12) Å	µ = 0.22 mm−1
β = 108.146 (2)º	T = 298 (2) K
V = 1756.4 (3) Å3	Block, colourless
Z = 4	0.42 × 0.37 × 0.15 mm

Bruker SMART CCD area-detector diffractometer	3078 independent reflections
Radiation source: fine-focus sealed tube	1752 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.045
T = 298(2) K	θmax = 25.0º
phi and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −7→11
Tmin = 0.913, Tmax = 0.968	k = −24→24
8674 measured reflections	l = −11→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0579P)2 + 0.2473P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
3078 reflections	Δρmax = 0.18 e Å−3
226 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Cl1	0.16106 (10)	0.55491 (4)	0.64505 (11)	0.0785 (4)
N1	0.5484 (2)	0.17758 (10)	0.9845 (2)	0.0446 (6)
C1	0.4223 (3)	0.18225 (12)	0.8698 (3)	0.0416 (7)
C2	0.3630 (3)	0.24170 (13)	0.8142 (3)	0.0448 (7)
H2	0.2764	0.2434	0.7337	0.054*
C3	0.4310 (3)	0.29874 (12)	0.8770 (3)	0.0431 (7)
C4	0.5590 (3)	0.29302 (13)	0.9955 (3)	0.0480 (7)
H4	0.6078	0.3301	1.0417	0.058*
C5	0.6160 (3)	0.23244 (13)	1.0465 (3)	0.0438 (7)
C6	0.3495 (3)	0.12018 (13)	0.8094 (3)	0.0438 (7)
C7	0.4301 (3)	0.06274 (13)	0.8358 (3)	0.0527 (8)
H7	0.5311	0.0635	0.8906	0.063*
C8	0.3629 (4)	0.00434 (15)	0.7821 (4)	0.0632 (9)
H8	0.4184	−0.0338	0.8006	0.076*
C9	0.2147 (4)	0.00284 (16)	0.7020 (4)	0.0645 (9)
H9	0.1695	−0.0364	0.6656	0.077*
C10	0.1321 (3)	0.05869 (16)	0.6747 (3)	0.0624 (9)
H10	0.0312	0.0573	0.6200	0.075*
C11	0.1988 (3)	0.11723 (14)	0.7284 (3)	0.0526 (8)
H11	0.1420	0.1550	0.7100	0.063*
C12	0.3669 (3)	0.36252 (12)	0.8200 (3)	0.0427 (7)
C13	0.3699 (3)	0.41388 (13)	0.9151 (3)	0.0508 (8)
H13	0.4152	0.4085	1.0160	0.061*
C14	0.3061 (3)	0.47293 (14)	0.8612 (4)	0.0546 (8)
H14	0.3076	0.5070	0.9256	0.066*
C15	0.2407 (3)	0.48093 (13)	0.7123 (4)	0.0500 (8)
C16	0.2377 (3)	0.43147 (14)	0.6161 (3)	0.0532 (8)
H16	0.1939	0.4376	0.5152	0.064*
C17	0.3001 (3)	0.37246 (13)	0.6697 (3)	0.0491 (8)
H17	0.2973	0.3387	0.6042	0.059*
C18	0.7568 (3)	0.22443 (13)	1.1695 (3)	0.0441 (7)
C19	0.8387 (3)	0.16759 (14)	1.1839 (3)	0.0563 (8)
H19	0.8018	0.1336	1.1187	0.068*
C20	0.9737 (3)	0.16067 (15)	1.2933 (4)	0.0633 (9)
H20	1.0271	0.1221	1.3016	0.076*
C21	1.0291 (3)	0.21002 (16)	1.3893 (4)	0.0622 (9)
H21	1.1217	0.2057	1.4614	0.075*
C22	0.9486 (4)	0.26599 (16)	1.3800 (4)	0.0684 (10)
H22	0.9851	0.2993	1.4472	0.082*
C23	0.8133 (3)	0.27280 (15)	1.2707 (4)	0.0651 (9)
H23	0.7591	0.3109	1.2652	0.078*

	U11	U22	U33	U12	U13	U23
Cl1	0.0786 (6)	0.0582 (5)	0.1004 (8)	0.0210 (4)	0.0301 (5)	0.0221 (5)
N1	0.0400 (14)	0.0478 (14)	0.0423 (14)	0.0003 (11)	0.0075 (11)	−0.0008 (11)
C1	0.0391 (17)	0.0479 (17)	0.0373 (17)	0.0008 (13)	0.0112 (13)	−0.0030 (13)
C2	0.0404 (17)	0.0510 (17)	0.0380 (17)	0.0031 (13)	0.0050 (13)	0.0015 (13)
C3	0.0408 (17)	0.0454 (17)	0.0411 (18)	0.0035 (13)	0.0098 (14)	0.0015 (13)
C4	0.0449 (18)	0.0458 (17)	0.0489 (19)	−0.0022 (13)	0.0080 (15)	−0.0029 (13)
C5	0.0387 (17)	0.0480 (17)	0.0432 (18)	0.0008 (13)	0.0106 (13)	−0.0014 (14)
C6	0.0407 (17)	0.0517 (17)	0.0369 (17)	−0.0026 (13)	0.0091 (13)	0.0008 (13)
C7	0.0480 (18)	0.0540 (19)	0.051 (2)	−0.0004 (15)	0.0078 (14)	−0.0045 (15)
C8	0.072 (2)	0.0497 (19)	0.066 (2)	0.0011 (16)	0.0181 (19)	−0.0051 (16)
C9	0.074 (3)	0.056 (2)	0.057 (2)	−0.0182 (18)	0.0115 (18)	−0.0064 (16)
C10	0.0508 (19)	0.075 (2)	0.052 (2)	−0.0160 (18)	0.0023 (15)	0.0003 (17)
C11	0.0493 (19)	0.0562 (19)	0.0466 (19)	−0.0013 (15)	0.0069 (15)	0.0036 (14)
C12	0.0371 (16)	0.0458 (16)	0.0428 (18)	0.0012 (12)	0.0090 (13)	0.0042 (13)
C13	0.0524 (19)	0.0510 (18)	0.0454 (19)	0.0024 (14)	0.0100 (15)	−0.0012 (14)
C14	0.058 (2)	0.0468 (18)	0.061 (2)	0.0002 (14)	0.0202 (17)	−0.0057 (15)
C15	0.0457 (18)	0.0511 (18)	0.057 (2)	0.0067 (13)	0.0215 (16)	0.0108 (15)
C16	0.0532 (19)	0.063 (2)	0.0435 (19)	0.0119 (15)	0.0147 (15)	0.0077 (15)
C17	0.0497 (18)	0.0534 (18)	0.0438 (19)	0.0077 (14)	0.0140 (14)	0.0008 (14)
C18	0.0391 (17)	0.0496 (17)	0.0411 (18)	−0.0013 (13)	0.0087 (13)	−0.0008 (13)
C19	0.051 (2)	0.0526 (19)	0.057 (2)	0.0014 (14)	0.0049 (16)	−0.0033 (15)
C20	0.047 (2)	0.062 (2)	0.070 (2)	0.0055 (15)	0.0033 (17)	0.0071 (18)
C21	0.0426 (19)	0.078 (2)	0.055 (2)	−0.0050 (17)	0.0003 (15)	0.0055 (18)
C22	0.060 (2)	0.074 (2)	0.058 (2)	−0.0034 (18)	0.0004 (17)	−0.0150 (18)
C23	0.056 (2)	0.062 (2)	0.064 (2)	0.0083 (16)	0.0000 (17)	−0.0129 (17)

Cl1—C15	1.732 (3)	C11—H11	0.9300
N1—C5	1.341 (3)	C12—C17	1.389 (4)
N1—C1	1.343 (3)	C12—C13	1.389 (4)
C1—C2	1.382 (3)	C13—C14	1.384 (4)
C1—C6	1.481 (4)	C13—H13	0.9300
C2—C3	1.382 (4)	C14—C15	1.370 (4)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.375 (4)	C15—C16	1.366 (4)
C3—C12	1.478 (3)	C16—C17	1.378 (4)
C4—C5	1.386 (3)	C16—H16	0.9300
C4—H4	0.9300	C17—H17	0.9300
C5—C18	1.479 (4)	C18—C23	1.374 (4)
C6—C7	1.386 (4)	C18—C19	1.385 (4)
C6—C11	1.387 (3)	C19—C20	1.376 (4)
C7—C8	1.382 (4)	C19—H19	0.9300
C7—H7	0.9300	C20—C21	1.359 (4)
C8—C9	1.365 (4)	C20—H20	0.9300
C8—H8	0.9300	C21—C22	1.368 (4)
C9—C10	1.368 (4)	C21—H21	0.9300
C9—H9	0.9300	C22—C23	1.378 (4)
C10—C11	1.383 (4)	C22—H22	0.9300
C10—H10	0.9300	C23—H23	0.9300
C5—N1—C1	118.4 (2)	C17—C12—C3	120.8 (2)
N1—C1—C2	121.6 (2)	C13—C12—C3	121.0 (3)
N1—C1—C6	116.0 (2)	C14—C13—C12	120.7 (3)
C2—C1—C6	122.4 (2)	C14—C13—H13	119.7
C1—C2—C3	120.8 (3)	C12—C13—H13	119.7
C1—C2—H2	119.6	C15—C14—C13	119.6 (3)
C3—C2—H2	119.6	C15—C14—H14	120.2
C4—C3—C2	116.8 (2)	C13—C14—H14	120.2
C4—C3—C12	122.0 (2)	C16—C15—C14	121.0 (3)
C2—C3—C12	121.2 (2)	C16—C15—Cl1	119.5 (2)
C3—C4—C5	120.6 (3)	C14—C15—Cl1	119.5 (2)
C3—C4—H4	119.7	C15—C16—C17	119.5 (3)
C5—C4—H4	119.7	C15—C16—H16	120.3
N1—C5—C4	121.8 (3)	C17—C16—H16	120.3
N1—C5—C18	116.1 (2)	C16—C17—C12	121.1 (3)
C4—C5—C18	122.1 (2)	C16—C17—H17	119.4
C7—C6—C11	118.0 (2)	C12—C17—H17	119.4
C7—C6—C1	120.5 (2)	C23—C18—C19	117.6 (3)
C11—C6—C1	121.5 (2)	C23—C18—C5	122.0 (3)
C8—C7—C6	121.1 (3)	C19—C18—C5	120.4 (2)
C8—C7—H7	119.5	C20—C19—C18	121.0 (3)
C6—C7—H7	119.5	C20—C19—H19	119.5
C9—C8—C7	119.8 (3)	C18—C19—H19	119.5
C9—C8—H8	120.1	C21—C20—C19	120.1 (3)
C7—C8—H8	120.1	C21—C20—H20	119.9
C8—C9—C10	120.5 (3)	C19—C20—H20	119.9
C8—C9—H9	119.8	C20—C21—C22	120.0 (3)
C10—C9—H9	119.8	C20—C21—H21	120.0
C9—C10—C11	120.0 (3)	C22—C21—H21	120.0
C9—C10—H10	120.0	C21—C22—C23	119.8 (3)
C11—C10—H10	120.0	C21—C22—H22	120.1
C10—C11—C6	120.7 (3)	C23—C22—H22	120.1
C10—C11—H11	119.6	C18—C23—C22	121.4 (3)
C6—C11—H11	119.6	C18—C23—H23	119.3
C17—C12—C13	118.1 (2)	C22—C23—H23	119.3