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

Abstract

In the title compound, C₂₃H₁₆ClN, the crystal packing exhibits no significantly short inter­molecular 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 _r = 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) ų

• 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

• Δρ_max = 0.18 e Å⁻³

• Δρ_min = −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.

Supplementary Material

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

supplementary crystallographic information

Comment

In this paper,we present a new crystal, 4-(4^'-chlorophenyl)-2,6-diphenylpyridine, (I). In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in reported the compound (Ondracek et al., 1994).

The three phenyl rings display a disrotatory conformation and form different angles with the pyridine ring. The phenyl ring attached at C1 forms the smallest angle with the heterocycle, 20.8°, because there is only the free electron pair of the N atom and one H atom in the ortho positions. The angle formed by the phenyl ring attached at C5 is slightly larger - 22.39°. The remaining phenyl ring forms the largest angle with the heterocycle, 37.56°. Meanwhile,the crystal packing demonstrates no significantly short intermolecular contacts.

Experimental

4-chlorobenzaldehyde (0.3 mmol) and acetophenone (0.6 mmol) under boron trifluoride ether (0.1 mmol) as a catalyst, the mixture was mixed in 50 ml flask. After irradiating for 3 min at 375 W, the mixture was cooled slowly to room temperature and the title compound was then recrystallized from ethanol, affording the title compound as a colorless crystalline solid. Elemental analysis: calculated for C₂₃H₁₆ClN: C 80.81, H 4.72, N 4.10%; found: C 80.68, H 4.75, N 4.14%.

Refinement

All H atoms were positioned geometrically, with C—H=0.93- 0.98 Å, and refined as riding, with U_iso(H)=1.2U_eq(C).

Figures

Fig. 1.

ORTEP drawing of the title compound with atom numbering scheme and thermal ellipsoids at 30% probability level.

Crystal data

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

Data collection

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

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

Special details

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 (Ų)

	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*

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, °)

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