Literature DB >> 21579499

8-(4-Chloro-benzyl-idene)-4-(4-chloro-phen-yl)-2-phenyl-5,6,7,8-tetra-hydro-quinoline.

Fangfang Jian1, Xin Zhai.   

Abstract

In the crystal structure of the title compound, C(28)H(21)Cl(2)N, π-π inter-actions link pairs of mol-ecules into centrosymmetric dimers with a distance of 3.756 (3) Å between the centroids of the pyridine rings. Weak inter-molecular C-H⋯Cl hydrogen bonds further link these dimers into chains propagating along [01]. The pyridine ring forms dihedral angles of 21.52 (1) and 55.87 (2)°, respectively, with the phenyl ring and the 4-chlorophenyl ring.

Entities:  

Year:  2010        PMID： 21579499      PMCID： PMC2979525          DOI： 10.1107/S1600536810017769

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For applications of pyridyl-containing compounds, see: Yan et al. (2007 ▶); Barton & Ollis (1979 ▶); Katritzky & Marson (1984 ▶); Constable et al. (1994 ▶); Eryazici et al. (2006 ▶).

Experimental

Crystal data

C28H21Cl2N M = 442.36 Triclinic, a = 10.0583 (10) Å b = 10.6483 (10) Å c = 10.8792 (10) Å α = 82.028 (2)° β = 89.345 (1)° γ = 71.335 (2)° V = 1092.53 (18) Å3 Z = 2 Mo Kα radiation μ = 0.31 mm−1 T = 295 K 0.23 × 0.20 × 0.19 mm

Data collection

Enraf–Nonius CAD-4 diffractometer 5765 measured reflections 3810 independent reflections 3211 reflections with I > 2σ(I) R int = 0.014 3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.036 wR(F 2) = 0.102 S = 1.06 3810 reflections 280 parameters H-atom parameters constrained Δρmax = 0.20 e Å−3 Δρmin = −0.30 e Å−3 Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017769/cv2704sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017769/cv2704Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C28H21Cl2NZ = 2
Mr = 442.36F(000) = 460
Triclinic, P1Dx = 1.345 Mg m−3
Hall symbol: -P 1Melting point: 446 K
a = 10.0583 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.6483 (10) ÅCell parameters from 25 reflections
c = 10.8792 (10) Åθ = 4–14°
α = 82.028 (2)°µ = 0.31 mm−1
β = 89.345 (1)°T = 295 K
γ = 71.335 (2)°Block, colorless
V = 1092.53 (18) Å30.23 × 0.20 × 0.19 mm
Enraf–Nonius CAD-4 diffractometerRint = 0.014
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 1.9°
graphiteh = −10→11
ω scansk = −10→12
5765 measured reflectionsl = −12→12
3810 independent reflections3 standard reflections every 100 reflections
3211 reflections with I > 2σ(I) intensity decay: none
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.049P)2 + 0.2862P] where P = (Fo2 + 2Fc2)/3
3810 reflections(Δ/σ)max < 0.001
280 parametersΔρmax = 0.20 e Å−3
0 restraintsΔρmin = −0.30 e Å−3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.
xyzUiso*/Ueq
Cl10.76136 (6)−0.12681 (6)−0.49616 (5)0.06911 (19)
Cl2−0.44155 (6)0.60618 (5)0.38242 (6)0.0742 (2)
N10.17509 (14)−0.06763 (13)0.09541 (12)0.0368 (3)
C10.45331 (19)−0.14359 (18)−0.27005 (16)0.0451 (4)
H1B0.3983−0.1989−0.25220.054*
C20.5506 (2)−0.17024 (19)−0.36113 (17)0.0489 (4)
H2A0.5600−0.2415−0.40490.059*
C30.63328 (18)−0.09032 (19)−0.38617 (16)0.0458 (4)
C40.61789 (19)0.0167 (2)−0.32375 (17)0.0499 (5)
H4A0.67400.0710−0.34200.060*
C50.51923 (19)0.04352 (18)−0.23411 (16)0.0451 (4)
H5A0.50890.1167−0.19280.054*
C60.43443 (17)−0.03640 (16)−0.20368 (15)0.0374 (4)
C70.33130 (17)−0.02208 (16)−0.10601 (15)0.0379 (4)
H7A0.2986−0.0948−0.08810.045*
C80.27524 (16)0.07649 (16)−0.03750 (15)0.0350 (4)
C90.30828 (19)0.20661 (17)−0.04971 (16)0.0416 (4)
H9A0.28200.2535−0.13330.050*
H9B0.40880.1863−0.03800.050*
C100.23390 (19)0.29860 (17)0.04218 (17)0.0441 (4)
H10A0.28000.26520.12350.053*
H10B0.24050.38730.01660.053*
C110.08054 (18)0.30767 (16)0.05054 (16)0.0424 (4)
H11A0.03440.36940.10730.051*
H11B0.03360.3405−0.03050.051*
C120.07233 (17)0.17042 (16)0.09631 (14)0.0355 (4)
C130.17015 (16)0.05872 (16)0.05496 (14)0.0345 (4)
C140.08518 (17)−0.08920 (16)0.18078 (15)0.0369 (4)
C150.09818 (18)−0.23138 (16)0.22446 (15)0.0386 (4)
C160.2229 (2)−0.33247 (17)0.21094 (17)0.0473 (4)
H16A0.2978−0.31080.17350.057*
C170.2370 (2)−0.46471 (19)0.25232 (19)0.0578 (5)
H17A0.3211−0.53130.24260.069*
C180.1272 (3)−0.4986 (2)0.30786 (19)0.0610 (6)
H18A0.1370−0.58770.33610.073*
C190.0030 (2)−0.3998 (2)0.32122 (18)0.0578 (5)
H19A−0.0716−0.42230.35850.069*
C20−0.0120 (2)−0.26712 (18)0.27962 (16)0.0469 (4)
H20A−0.0968−0.20110.28870.056*
C21−0.01285 (18)0.01573 (17)0.22810 (15)0.0399 (4)
H21A−0.0728−0.00210.28870.048*
C22−0.02151 (17)0.14700 (16)0.18517 (15)0.0369 (4)
C23−0.12942 (17)0.25829 (16)0.23450 (15)0.0380 (4)
C24−0.13747 (19)0.26296 (18)0.36124 (16)0.0460 (4)
H24A−0.07630.19440.41580.055*
C25−0.2349 (2)0.3679 (2)0.40779 (18)0.0513 (5)
H25A−0.23890.37060.49290.062*
C26−0.32574 (19)0.46814 (18)0.32692 (18)0.0467 (4)
C27−0.32402 (19)0.46397 (18)0.20151 (17)0.0472 (4)
H27A−0.38840.53070.14780.057*
C28−0.22516 (19)0.35909 (18)0.15609 (16)0.0444 (4)
H28A−0.22300.35630.07100.053*
U11U22U33U12U13U23
Cl10.0586 (3)0.0873 (4)0.0505 (3)−0.0087 (3)0.0250 (2)−0.0108 (3)
Cl20.0743 (4)0.0533 (3)0.0875 (4)−0.0030 (3)0.0244 (3)−0.0288 (3)
N10.0408 (8)0.0361 (7)0.0351 (7)−0.0139 (6)0.0084 (6)−0.0076 (6)
C10.0467 (10)0.0434 (10)0.0459 (10)−0.0140 (8)0.0093 (8)−0.0106 (8)
C20.0527 (11)0.0490 (11)0.0418 (10)−0.0086 (9)0.0090 (8)−0.0146 (8)
C30.0396 (9)0.0550 (11)0.0329 (9)−0.0034 (8)0.0076 (7)−0.0024 (8)
C40.0466 (10)0.0575 (11)0.0476 (10)−0.0201 (9)0.0113 (8)−0.0067 (9)
C50.0487 (10)0.0481 (10)0.0433 (10)−0.0199 (8)0.0123 (8)−0.0129 (8)
C60.0365 (9)0.0383 (9)0.0341 (8)−0.0079 (7)0.0044 (7)−0.0047 (7)
C70.0384 (9)0.0370 (9)0.0394 (9)−0.0139 (7)0.0063 (7)−0.0058 (7)
C80.0359 (8)0.0346 (8)0.0340 (8)−0.0112 (7)0.0044 (7)−0.0043 (7)
C90.0459 (10)0.0403 (9)0.0420 (9)−0.0179 (8)0.0111 (8)−0.0083 (7)
C100.0540 (11)0.0386 (9)0.0459 (10)−0.0221 (8)0.0124 (8)−0.0107 (8)
C110.0495 (10)0.0340 (9)0.0435 (10)−0.0126 (8)0.0118 (8)−0.0075 (7)
C120.0390 (9)0.0358 (8)0.0335 (8)−0.0138 (7)0.0046 (7)−0.0068 (7)
C130.0375 (8)0.0347 (8)0.0324 (8)−0.0128 (7)0.0042 (7)−0.0061 (7)
C140.0412 (9)0.0366 (9)0.0341 (8)−0.0140 (7)0.0048 (7)−0.0060 (7)
C150.0501 (10)0.0369 (9)0.0318 (8)−0.0172 (8)0.0051 (7)−0.0079 (7)
C160.0546 (11)0.0410 (10)0.0474 (10)−0.0159 (9)0.0080 (8)−0.0092 (8)
C170.0697 (13)0.0384 (10)0.0611 (12)−0.0105 (10)0.0032 (10)−0.0101 (9)
C180.0920 (16)0.0391 (10)0.0557 (12)−0.0284 (11)−0.0012 (11)−0.0016 (9)
C190.0783 (14)0.0561 (12)0.0498 (11)−0.0386 (11)0.0104 (10)−0.0032 (9)
C200.0570 (11)0.0467 (10)0.0413 (10)−0.0223 (9)0.0104 (8)−0.0075 (8)
C210.0427 (9)0.0415 (9)0.0376 (9)−0.0163 (8)0.0123 (7)−0.0071 (7)
C220.0380 (9)0.0380 (9)0.0351 (9)−0.0116 (7)0.0053 (7)−0.0081 (7)
C230.0385 (9)0.0375 (9)0.0413 (9)−0.0156 (7)0.0098 (7)−0.0089 (7)
C240.0453 (10)0.0474 (10)0.0414 (10)−0.0088 (8)0.0056 (8)−0.0087 (8)
C250.0536 (11)0.0579 (12)0.0438 (10)−0.0153 (9)0.0106 (9)−0.0192 (9)
C260.0459 (10)0.0398 (10)0.0579 (11)−0.0161 (8)0.0174 (9)−0.0149 (8)
C270.0452 (10)0.0391 (10)0.0522 (11)−0.0094 (8)0.0067 (8)0.0004 (8)
C280.0490 (10)0.0446 (10)0.0387 (9)−0.0144 (8)0.0093 (8)−0.0049 (8)
Cl1—C31.7366 (17)C12—C221.397 (2)
Cl2—C261.7367 (17)C12—C131.405 (2)
N1—C141.337 (2)C14—C211.389 (2)
N1—C131.342 (2)C14—C151.487 (2)
C1—C21.378 (2)C15—C201.387 (2)
C1—C61.395 (2)C15—C161.389 (2)
C1—H1B0.9300C16—C171.380 (3)
C2—C31.368 (3)C16—H16A0.9300
C2—H2A0.9300C17—C181.376 (3)
C3—C41.373 (3)C17—H17A0.9300
C4—C51.375 (2)C18—C191.373 (3)
C4—H4A0.9300C18—H18A0.9300
C5—C61.393 (2)C19—C201.383 (3)
C5—H5A0.9300C19—H19A0.9300
C6—C71.465 (2)C20—H20A0.9300
C7—C81.343 (2)C21—C221.386 (2)
C7—H7A0.9300C21—H21A0.9300
C8—C131.489 (2)C22—C231.487 (2)
C8—C91.513 (2)C23—C281.382 (2)
C9—C101.518 (2)C23—C241.387 (2)
C9—H9A0.9700C24—C251.382 (2)
C9—H9B0.9700C24—H24A0.9300
C10—C111.517 (2)C25—C261.372 (3)
C10—H10A0.9700C25—H25A0.9300
C10—H10B0.9700C26—C271.371 (3)
C11—C121.505 (2)C27—C281.382 (2)
C11—H11A0.9700C27—H27A0.9300
C11—H11B0.9700C28—H28A0.9300
C14—N1—C13118.91 (14)N1—C13—C8116.56 (13)
C2—C1—C6122.23 (17)C12—C13—C8120.52 (14)
C2—C1—H1B118.9N1—C14—C21121.64 (15)
C6—C1—H1B118.9N1—C14—C15116.46 (14)
C3—C2—C1119.02 (17)C21—C14—C15121.88 (14)
C3—C2—H2A120.5C20—C15—C16118.21 (16)
C1—C2—H2A120.5C20—C15—C14121.62 (16)
C2—C3—C4120.79 (16)C16—C15—C14120.16 (15)
C2—C3—Cl1119.54 (14)C17—C16—C15120.80 (18)
C4—C3—Cl1119.66 (15)C17—C16—H16A119.6
C3—C4—C5119.74 (18)C15—C16—H16A119.6
C3—C4—H4A120.1C18—C17—C16120.35 (19)
C5—C4—H4A120.1C18—C17—H17A119.8
C4—C5—C6121.59 (17)C16—C17—H17A119.8
C4—C5—H5A119.2C19—C18—C17119.53 (18)
C6—C5—H5A119.2C19—C18—H18A120.2
C5—C6—C1116.61 (15)C17—C18—H18A120.2
C5—C6—C7126.52 (15)C18—C19—C20120.41 (19)
C1—C6—C7116.83 (15)C18—C19—H19A119.8
C8—C7—C6131.97 (16)C20—C19—H19A119.8
C8—C7—H7A114.0C19—C20—C15120.70 (19)
C6—C7—H7A114.0C19—C20—H20A119.7
C7—C8—C13117.97 (14)C15—C20—H20A119.7
C7—C8—C9124.69 (14)C22—C21—C14120.16 (15)
C13—C8—C9117.31 (13)C22—C21—H21A119.9
C8—C9—C10113.80 (13)C14—C21—H21A119.9
C8—C9—H9A108.8C21—C22—C12118.56 (15)
C10—C9—H9A108.8C21—C22—C23119.49 (14)
C8—C9—H9B108.8C12—C22—C23121.95 (14)
C10—C9—H9B108.8C28—C23—C24118.10 (16)
H9A—C9—H9B107.7C28—C23—C22121.24 (15)
C11—C10—C9111.40 (14)C24—C23—C22120.66 (16)
C11—C10—H10A109.3C25—C24—C23121.08 (17)
C9—C10—H10A109.3C25—C24—H24A119.5
C11—C10—H10B109.3C23—C24—H24A119.5
C9—C10—H10B109.3C26—C25—C24119.17 (17)
H10A—C10—H10B108.0C26—C25—H25A120.4
C12—C11—C10108.64 (14)C24—C25—H25A120.4
C12—C11—H11A110.0C27—C26—C25121.19 (17)
C10—C11—H11A110.0C27—C26—Cl2118.83 (15)
C12—C11—H11B110.0C25—C26—Cl2119.95 (15)
C10—C11—H11B110.0C26—C27—C28119.02 (17)
H11A—C11—H11B108.3C26—C27—H27A120.5
C22—C12—C13117.77 (14)C28—C27—H27A120.5
C22—C12—C11123.25 (14)C23—C28—C27121.37 (16)
C13—C12—C11118.81 (14)C23—C28—H28A119.3
N1—C13—C12122.92 (14)C27—C28—H28A119.3
D—H···AD—HH···AD···AD—H···A
C7—H7A···N10.932.342.760 (2)107
C20—H20A···Cl1i0.932.803.476 (2)130
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C20—H20A⋯Cl1i0.932.803.476 (2)130

Symmetry code: (i) .

  2 in total

1.  Synthesis and single-crystal X-ray characterization of 4,4"-functionalized 4'-(4-bromophenyl)-2,2':6',2"-terpyridines.

Authors:  Ibrahim Eryazici; Charles N Moorefield; Semih Durmus; George R Newkome
Journal:  J Org Chem       Date:  2006-02-03       Impact factor: 4.354

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
  2 in total

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