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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o186.
Published online 2007 December 6. doi:  10.1107/S1600536807064380
PMCID: PMC2915249

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 [triangle]).

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Object name is e-64-0o186-scheme1.jpg

Experimental

Crystal data

  • C23H16ClN
  • M r = 341.82
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o186-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a [triangle]); molecular graphics: SHELXTL (Sheldrick, 1997b [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

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

Acknowledgments

The authors acknowledge the support of the National Natural Science Foundation of Liaocheng University (No. X051040).

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 Uiso(H)=1.2Ueq(C).

Figures

Fig. 1.
ORTEP drawing of the title compound with atom numbering scheme and thermal ellipsoids at 30% probability level.

Crystal data

C23H16ClNF000 = 712
Mr = 341.82Dx = 1.293 Mg m3
Monoclinic, P2(1)/cMo Kα radiation λ = 0.71073 Å
a = 9.3995 (11) ÅCell parameters from 1970 reflections
b = 20.621 (2) Åθ = 2.3–25.2º
c = 9.5362 (12) ŵ = 0.22 mm1
β = 108.146 (2)ºT = 298 (2) K
V = 1756.4 (3) Å3Block, colourless
Z = 40.42 × 0.37 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer3078 independent reflections
Radiation source: fine-focus sealed tube1752 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.045
T = 298(2) Kθmax = 25.0º
phi and ω scansθmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −7→11
Tmin = 0.913, Tmax = 0.968k = −24→24
8674 measured reflectionsl = −11→11

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-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 reflectionsΔρmax = 0.18 e Å3
226 parametersΔρmin = −0.24 e Å3
Primary atom site location: structure-invariant direct methodsExtinction 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 (Å2)

xyzUiso*/Ueq
Cl10.16106 (10)0.55491 (4)0.64505 (11)0.0785 (4)
N10.5484 (2)0.17758 (10)0.9845 (2)0.0446 (6)
C10.4223 (3)0.18225 (12)0.8698 (3)0.0416 (7)
C20.3630 (3)0.24170 (13)0.8142 (3)0.0448 (7)
H20.27640.24340.73370.054*
C30.4310 (3)0.29874 (12)0.8770 (3)0.0431 (7)
C40.5590 (3)0.29302 (13)0.9955 (3)0.0480 (7)
H40.60780.33011.04170.058*
C50.6160 (3)0.23244 (13)1.0465 (3)0.0438 (7)
C60.3495 (3)0.12018 (13)0.8094 (3)0.0438 (7)
C70.4301 (3)0.06274 (13)0.8358 (3)0.0527 (8)
H70.53110.06350.89060.063*
C80.3629 (4)0.00434 (15)0.7821 (4)0.0632 (9)
H80.4184−0.03380.80060.076*
C90.2147 (4)0.00284 (16)0.7020 (4)0.0645 (9)
H90.1695−0.03640.66560.077*
C100.1321 (3)0.05869 (16)0.6747 (3)0.0624 (9)
H100.03120.05730.62000.075*
C110.1988 (3)0.11723 (14)0.7284 (3)0.0526 (8)
H110.14200.15500.71000.063*
C120.3669 (3)0.36252 (12)0.8200 (3)0.0427 (7)
C130.3699 (3)0.41388 (13)0.9151 (3)0.0508 (8)
H130.41520.40851.01600.061*
C140.3061 (3)0.47293 (14)0.8612 (4)0.0546 (8)
H140.30760.50700.92560.066*
C150.2407 (3)0.48093 (13)0.7123 (4)0.0500 (8)
C160.2377 (3)0.43147 (14)0.6161 (3)0.0532 (8)
H160.19390.43760.51520.064*
C170.3001 (3)0.37246 (13)0.6697 (3)0.0491 (8)
H170.29730.33870.60420.059*
C180.7568 (3)0.22443 (13)1.1695 (3)0.0441 (7)
C190.8387 (3)0.16759 (14)1.1839 (3)0.0563 (8)
H190.80180.13361.11870.068*
C200.9737 (3)0.16067 (15)1.2933 (4)0.0633 (9)
H201.02710.12211.30160.076*
C211.0291 (3)0.21002 (16)1.3893 (4)0.0622 (9)
H211.12170.20571.46140.075*
C220.9486 (4)0.26599 (16)1.3800 (4)0.0684 (10)
H220.98510.29931.44720.082*
C230.8133 (3)0.27280 (15)1.2707 (4)0.0651 (9)
H230.75910.31091.26520.078*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0786 (6)0.0582 (5)0.1004 (8)0.0210 (4)0.0301 (5)0.0221 (5)
N10.0400 (14)0.0478 (14)0.0423 (14)0.0003 (11)0.0075 (11)−0.0008 (11)
C10.0391 (17)0.0479 (17)0.0373 (17)0.0008 (13)0.0112 (13)−0.0030 (13)
C20.0404 (17)0.0510 (17)0.0380 (17)0.0031 (13)0.0050 (13)0.0015 (13)
C30.0408 (17)0.0454 (17)0.0411 (18)0.0035 (13)0.0098 (14)0.0015 (13)
C40.0449 (18)0.0458 (17)0.0489 (19)−0.0022 (13)0.0080 (15)−0.0029 (13)
C50.0387 (17)0.0480 (17)0.0432 (18)0.0008 (13)0.0106 (13)−0.0014 (14)
C60.0407 (17)0.0517 (17)0.0369 (17)−0.0026 (13)0.0091 (13)0.0008 (13)
C70.0480 (18)0.0540 (19)0.051 (2)−0.0004 (15)0.0078 (14)−0.0045 (15)
C80.072 (2)0.0497 (19)0.066 (2)0.0011 (16)0.0181 (19)−0.0051 (16)
C90.074 (3)0.056 (2)0.057 (2)−0.0182 (18)0.0115 (18)−0.0064 (16)
C100.0508 (19)0.075 (2)0.052 (2)−0.0160 (18)0.0023 (15)0.0003 (17)
C110.0493 (19)0.0562 (19)0.0466 (19)−0.0013 (15)0.0069 (15)0.0036 (14)
C120.0371 (16)0.0458 (16)0.0428 (18)0.0012 (12)0.0090 (13)0.0042 (13)
C130.0524 (19)0.0510 (18)0.0454 (19)0.0024 (14)0.0100 (15)−0.0012 (14)
C140.058 (2)0.0468 (18)0.061 (2)0.0002 (14)0.0202 (17)−0.0057 (15)
C150.0457 (18)0.0511 (18)0.057 (2)0.0067 (13)0.0215 (16)0.0108 (15)
C160.0532 (19)0.063 (2)0.0435 (19)0.0119 (15)0.0147 (15)0.0077 (15)
C170.0497 (18)0.0534 (18)0.0438 (19)0.0077 (14)0.0140 (14)0.0008 (14)
C180.0391 (17)0.0496 (17)0.0411 (18)−0.0013 (13)0.0087 (13)−0.0008 (13)
C190.051 (2)0.0526 (19)0.057 (2)0.0014 (14)0.0049 (16)−0.0033 (15)
C200.047 (2)0.062 (2)0.070 (2)0.0055 (15)0.0033 (17)0.0071 (18)
C210.0426 (19)0.078 (2)0.055 (2)−0.0050 (17)0.0003 (15)0.0055 (18)
C220.060 (2)0.074 (2)0.058 (2)−0.0034 (18)0.0004 (17)−0.0150 (18)
C230.056 (2)0.062 (2)0.064 (2)0.0083 (16)0.0000 (17)−0.0129 (17)

Geometric parameters (Å, °)

Cl1—C151.732 (3)C11—H110.9300
N1—C51.341 (3)C12—C171.389 (4)
N1—C11.343 (3)C12—C131.389 (4)
C1—C21.382 (3)C13—C141.384 (4)
C1—C61.481 (4)C13—H130.9300
C2—C31.382 (4)C14—C151.370 (4)
C2—H20.9300C14—H140.9300
C3—C41.375 (4)C15—C161.366 (4)
C3—C121.478 (3)C16—C171.378 (4)
C4—C51.386 (3)C16—H160.9300
C4—H40.9300C17—H170.9300
C5—C181.479 (4)C18—C231.374 (4)
C6—C71.386 (4)C18—C191.385 (4)
C6—C111.387 (3)C19—C201.376 (4)
C7—C81.382 (4)C19—H190.9300
C7—H70.9300C20—C211.359 (4)
C8—C91.365 (4)C20—H200.9300
C8—H80.9300C21—C221.368 (4)
C9—C101.368 (4)C21—H210.9300
C9—H90.9300C22—C231.378 (4)
C10—C111.383 (4)C22—H220.9300
C10—H100.9300C23—H230.9300
C5—N1—C1118.4 (2)C17—C12—C3120.8 (2)
N1—C1—C2121.6 (2)C13—C12—C3121.0 (3)
N1—C1—C6116.0 (2)C14—C13—C12120.7 (3)
C2—C1—C6122.4 (2)C14—C13—H13119.7
C1—C2—C3120.8 (3)C12—C13—H13119.7
C1—C2—H2119.6C15—C14—C13119.6 (3)
C3—C2—H2119.6C15—C14—H14120.2
C4—C3—C2116.8 (2)C13—C14—H14120.2
C4—C3—C12122.0 (2)C16—C15—C14121.0 (3)
C2—C3—C12121.2 (2)C16—C15—Cl1119.5 (2)
C3—C4—C5120.6 (3)C14—C15—Cl1119.5 (2)
C3—C4—H4119.7C15—C16—C17119.5 (3)
C5—C4—H4119.7C15—C16—H16120.3
N1—C5—C4121.8 (3)C17—C16—H16120.3
N1—C5—C18116.1 (2)C16—C17—C12121.1 (3)
C4—C5—C18122.1 (2)C16—C17—H17119.4
C7—C6—C11118.0 (2)C12—C17—H17119.4
C7—C6—C1120.5 (2)C23—C18—C19117.6 (3)
C11—C6—C1121.5 (2)C23—C18—C5122.0 (3)
C8—C7—C6121.1 (3)C19—C18—C5120.4 (2)
C8—C7—H7119.5C20—C19—C18121.0 (3)
C6—C7—H7119.5C20—C19—H19119.5
C9—C8—C7119.8 (3)C18—C19—H19119.5
C9—C8—H8120.1C21—C20—C19120.1 (3)
C7—C8—H8120.1C21—C20—H20119.9
C8—C9—C10120.5 (3)C19—C20—H20119.9
C8—C9—H9119.8C20—C21—C22120.0 (3)
C10—C9—H9119.8C20—C21—H21120.0
C9—C10—C11120.0 (3)C22—C21—H21120.0
C9—C10—H10120.0C21—C22—C23119.8 (3)
C11—C10—H10120.0C21—C22—H22120.1
C10—C11—C6120.7 (3)C23—C22—H22120.1
C10—C11—H11119.6C18—C23—C22121.4 (3)
C6—C11—H11119.6C18—C23—H23119.3
C17—C12—C13118.1 (2)C22—C23—H23119.3

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AV2004).

References

  • Ondrácek, J., Novotný, J., Petru, M., Lhoták, P. & Kuthan, J. (1994). Acta Cryst C50, 1809–1811.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography