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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o831.
Published online 2008 April 10. doi:  10.1107/S1600536808009239
PMCID: PMC2961081

2-Chloro-12-phenyl-6,7,8,9,10,11-hexa­hydro­cyclo­octa­[b]quinoline

Abstract

In the mol­ecule of the title compound, C21H20ClN, the quinoline group is nearly planar and is oriented at a dihedral angle of 77.21 (3)° with respect to the phenyl ring. The conformation of the cyclooctane ring is twist-boat. In the crystal structure, there are some weak π–π inter­actions [centroid-to-centroid distances of 3.7414 (11) and 3.8633 (12) Å] between the rings of the quinoline groups.

Related literature

For general background, see: Kalluraya & Sreenivasa (1998 [triangle]); Doube et al. (1998 [triangle]); Maguire et al. (1994 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-64-0o831-scheme1.jpg

Experimental

Crystal data

  • C21H20ClN
  • M r = 321.83
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o831-efi1.jpg
  • a = 9.837 (2) Å
  • b = 9.980 (2) Å
  • c = 10.175 (2) Å
  • α = 74.600 (17)°
  • β = 70.575 (16)°
  • γ = 61.829 (15)°
  • V = 823.4 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 298 (2) K
  • 0.5 × 0.5 × 0.25 mm

Data collection

  • Stoe IPDSII diffractometer
  • Absorption correction: numerical; shape of crystal determined optically (X-RED and X-SHAPE; Stoe & Cie, 2002 [triangle]) T min = 0.889, T max = 0.949
  • 8123 measured reflections
  • 3801 independent reflections
  • 3493 reflections with I > 2σ(I)
  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.126
  • S = 1.03
  • 3801 reflections
  • 208 parameters
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 [triangle]); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009239/hk2449sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009239/hk2449Isup2.hkl

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

Acknowledgments

The author is grateful to the Islamic Azad University, Dorood Branch, for financial support.

supplementary crystallographic information

Comment

Quinoline nucleus is a backbone of many natural products and pharmacologicallly significant compounds displaying a broad range of biological activities and many functionalized quinolines are widely used as antimalarial, antiasthmatic, antiinflamatory, antibacterial, antihypertensive and tyrosine kinase PDGF-RTK inhibiting agents (Kalluraya & Sreenivasa, 1998; Doube et al., 1998; Maguire et al., 1994). We report herein the synthesis and crystal structure of the title compound, (I).

In the molecule of the title compound, (I), (Fig. 1) the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6), B (N1/C1/C6-C8/C15) and C (C16-C21) are, of course, planar, and they are oriented at dihedral angles of A/B = 0.88 (3)°, A/C = 76.76 (4)° and B/C = 77.64 (3)°. So, rings A and B are also nearly coplanar. The dihedral angle between the coplanar ring system and ring C is 77.21 (3)°.

In the crystal structure, the weak π–π interactions between the two adjacent A rings and A and B rings, with centroid-centroid distances of 3.7414 (11) Å and 3.8633 (12) Å, may be effective in the stabilization of the structure (Fig. 2).

Experimental

A mixture of 2-amino-5-chlorophenyl(phenyl)methanone (0.23 g, 1 mmol), cyclooctanone (1.26 g, 1 mmol) and Dewax-50 W ion exchange resin (0.3 g) was heated at 353 K. After 2 h the reaction mixture was washed with ethyl acetate (10 ml). Evaporation of the solvent followed by recrystallization from ethanol to afford the pure product (yield; 0.278 g, 75%).

Refinement

H atoms were positioned geometrically with C-H = 0.93 and 0.97 Å for aromatic and methylene H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A packing diagram of (I).

Crystal data

C21H20Cl1N1Z = 2
Mr = 321.83F000 = 340
Triclinic, P1Dx = 1.298 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 9.837 (2) ÅCell parameters from 2086 reflections
b = 9.980 (2) Åθ = 2.4–28.0º
c = 10.175 (2) ŵ = 0.23 mm1
α = 74.600 (17)ºT = 298 (2) K
β = 70.575 (16)ºBlock, colorless
γ = 61.829 (15)º0.5 × 0.5 × 0.25 mm
V = 823.4 (3) Å3

Data collection

Stoe IPDSII diffractometerRint = 0.045
rotation method scansθmax = 28.0º
Absorption correction: numericalshape of crystal determined optically [PROGRAM NAME? reference?θmin = 2.4º
Tmin = 0.889, Tmax = 0.949h = −12→11
8123 measured reflectionsk = −13→10
3801 independent reflectionsl = −13→13
3493 reflections with I > 2σ(I)

Refinement

Refinement on F2H-atom parameters constrained
Least-squares matrix: full  w = 1/[σ2(Fo2) + (0.0607P)2 + 0.1883P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.046(Δ/σ)max = 0.006
wR(F2) = 0.126Δρmax = 0.25 e Å3
S = 1.04Δρmin = −0.19 e Å3
3801 reflectionsExtinction correction: none
208 parameters

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.

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

xyzUiso*/Ueq
Cl10.59962 (5)0.96565 (4)0.17975 (4)0.06276 (16)
N10.51106 (12)0.54812 (13)0.69575 (11)0.0391 (2)
C10.53821 (13)0.64045 (14)0.57445 (12)0.0354 (2)
C20.42557 (15)0.79582 (15)0.56208 (15)0.0440 (3)
H20.33770.83130.63660.053*
C30.44417 (16)0.89348 (15)0.44312 (16)0.0462 (3)
H30.36930.99490.43540.055*
C40.57823 (15)0.83909 (14)0.33177 (14)0.0418 (3)
C50.69071 (14)0.69125 (14)0.33901 (13)0.0392 (3)
H50.77870.6590.26390.047*
C60.67271 (13)0.58733 (13)0.46148 (12)0.0333 (2)
C70.78256 (13)0.43037 (13)0.47776 (12)0.0339 (2)
C80.75403 (14)0.33702 (14)0.60027 (12)0.0357 (2)
C90.86347 (17)0.16885 (15)0.62161 (14)0.0456 (3)
H9A0.91110.13130.5310.055*
H9B0.80030.11390.67960.055*
C100.99695 (16)0.13077 (18)0.69016 (16)0.0542 (4)
H10A1.04550.02070.71670.065*
H10B1.07770.15840.620.065*
C110.94953 (18)0.2078 (2)0.81886 (16)0.0549 (4)
H11A0.90850.31780.79090.066*
H11B1.04450.17650.85010.066*
C120.82614 (19)0.17430 (19)0.94328 (16)0.0553 (4)
H12A0.85680.16061.02890.066*
H12B0.82890.0780.9360.066*
C130.65535 (18)0.29655 (18)0.95684 (14)0.0510 (3)
H13A0.65510.39480.95290.061*
H13B0.59270.27481.04910.061*
C140.57222 (16)0.31198 (17)0.84728 (14)0.0470 (3)
H14A0.59880.21010.83070.056*
H14B0.45820.36050.88550.056*
C150.61401 (13)0.40276 (14)0.70838 (12)0.0370 (3)
C160.92569 (13)0.37293 (13)0.35925 (12)0.0359 (2)
C170.91195 (17)0.34403 (19)0.23968 (14)0.0498 (3)
H170.81390.35750.23350.06*
C181.0449 (2)0.2949 (2)0.12879 (17)0.0655 (5)
H181.03550.27460.04890.079*
C191.1906 (2)0.2758 (2)0.13600 (18)0.0631 (4)
H191.27920.24210.06170.076*
C201.20421 (17)0.30678 (19)0.25315 (18)0.0564 (4)
H201.3020.29550.25780.068*
C211.07270 (15)0.35483 (16)0.36480 (15)0.0453 (3)
H211.0830.37520.44420.054*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0600 (3)0.0434 (2)0.0641 (3)−0.01716 (17)−0.01096 (18)0.01044 (16)
N10.0288 (5)0.0426 (5)0.0396 (5)−0.0107 (4)−0.0059 (4)−0.0076 (4)
C10.0271 (5)0.0369 (6)0.0400 (6)−0.0093 (4)−0.0084 (4)−0.0094 (4)
C20.0304 (6)0.0392 (6)0.0524 (7)−0.0063 (5)−0.0053 (5)−0.0130 (5)
C30.0367 (6)0.0334 (6)0.0607 (8)−0.0071 (5)−0.0131 (6)−0.0078 (5)
C40.0396 (6)0.0357 (6)0.0486 (7)−0.0157 (5)−0.0132 (5)−0.0006 (5)
C50.0327 (6)0.0376 (6)0.0426 (6)−0.0123 (5)−0.0068 (5)−0.0059 (5)
C60.0268 (5)0.0346 (5)0.0377 (5)−0.0102 (4)−0.0084 (4)−0.0083 (4)
C70.0277 (5)0.0358 (6)0.0366 (5)−0.0095 (4)−0.0080 (4)−0.0096 (4)
C80.0318 (5)0.0346 (6)0.0391 (6)−0.0103 (4)−0.0104 (4)−0.0074 (4)
C90.0475 (7)0.0333 (6)0.0455 (7)−0.0086 (5)−0.0103 (5)−0.0065 (5)
C100.0372 (7)0.0478 (7)0.0542 (8)−0.0030 (6)−0.0116 (6)0.0008 (6)
C110.0457 (7)0.0622 (9)0.0552 (8)−0.0218 (7)−0.0207 (6)0.0034 (7)
C120.0548 (8)0.0573 (9)0.0470 (7)−0.0206 (7)−0.0186 (6)0.0057 (6)
C130.0531 (8)0.0526 (8)0.0366 (6)−0.0188 (6)−0.0069 (5)−0.0013 (5)
C140.0372 (6)0.0509 (7)0.0463 (7)−0.0197 (6)−0.0053 (5)−0.0001 (6)
C150.0301 (5)0.0413 (6)0.0387 (6)−0.0142 (5)−0.0091 (4)−0.0050 (5)
C160.0308 (5)0.0325 (5)0.0378 (6)−0.0083 (4)−0.0052 (4)−0.0085 (4)
C170.0420 (7)0.0655 (9)0.0450 (7)−0.0231 (6)−0.0054 (5)−0.0178 (6)
C180.0635 (10)0.0914 (13)0.0468 (8)−0.0362 (9)0.0029 (7)−0.0309 (8)
C190.0472 (8)0.0739 (11)0.0574 (9)−0.0243 (8)0.0123 (7)−0.0265 (8)
C200.0323 (6)0.0617 (9)0.0695 (9)−0.0167 (6)−0.0022 (6)−0.0190 (7)
C210.0348 (6)0.0471 (7)0.0513 (7)−0.0118 (5)−0.0087 (5)−0.0152 (6)

Geometric parameters (Å, °)

C1—N11.3612 (16)C11—H11A0.97
C1—C61.4153 (16)C11—H11B0.97
C1—C21.4194 (17)C12—C131.526 (2)
C2—C31.358 (2)C12—H12A0.97
C2—H20.93C12—H12B0.97
C3—C41.4051 (19)C13—C141.527 (2)
C3—H30.93C13—H13A0.97
C4—C51.3644 (18)C13—H13B0.97
C4—Cl11.7405 (14)C14—C151.5075 (18)
C5—C61.4143 (17)C14—H14A0.97
C5—H50.93C14—H14B0.97
C6—C71.4255 (16)C15—N11.3217 (17)
C7—C81.3777 (17)C16—C171.3836 (18)
C7—C161.4969 (16)C16—C211.3890 (18)
C8—C151.4353 (17)C17—C181.390 (2)
C8—C91.5096 (17)C17—H170.93
C9—C101.534 (2)C18—C191.378 (3)
C9—H9A0.97C18—H180.93
C9—H9B0.97C19—C201.370 (2)
C10—C111.521 (2)C19—H190.93
C10—H10A0.97C20—C211.3857 (19)
C10—H10B0.97C20—H200.93
C11—C121.524 (2)C21—H210.93
N1—C1—C6122.66 (11)H11A—C11—H11B107.4
N1—C1—C2117.98 (11)C11—C12—C13115.65 (13)
C6—C1—C2119.36 (11)C11—C12—H12A108.4
C3—C2—C1121.00 (12)C13—C12—H12A108.4
C3—C2—H2119.5C11—C12—H12B108.4
C1—C2—H2119.5C13—C12—H12B108.4
C2—C3—C4119.00 (12)H12A—C12—H12B107.4
C2—C3—H3120.5C12—C13—C14116.62 (13)
C4—C3—H3120.5C12—C13—H13A108.1
C5—C4—C3122.25 (12)C14—C13—H13A108.1
C5—C4—Cl1119.37 (10)C12—C13—H13B108.1
C3—C4—Cl1118.37 (10)C14—C13—H13B108.1
C4—C5—C6119.61 (11)H13A—C13—H13B107.3
C4—C5—H5120.2C15—C14—C13114.79 (11)
C6—C5—H5120.2C15—C14—H14A108.6
C5—C6—C1118.77 (11)C13—C14—H14A108.6
C5—C6—C7123.61 (10)C15—C14—H14B108.6
C1—C6—C7117.63 (11)C13—C14—H14B108.6
C8—C7—C6119.53 (10)H14A—C14—H14B107.5
C8—C7—C16122.32 (10)N1—C15—C8123.17 (11)
C6—C7—C16118.15 (10)N1—C15—C14114.02 (11)
C7—C8—C15118.28 (11)C8—C15—C14122.80 (11)
C7—C8—C9121.86 (11)C17—C16—C21118.98 (11)
C15—C8—C9119.85 (11)C17—C16—C7120.43 (11)
C8—C9—C10115.07 (12)C21—C16—C7120.52 (11)
C8—C9—H9A108.5C16—C17—C18119.87 (13)
C10—C9—H9A108.5C16—C17—H17120.1
C8—C9—H9B108.5C18—C17—H17120.1
C10—C9—H9B108.5C19—C18—C17120.65 (15)
H9A—C9—H9B107.5C19—C18—H18119.7
C11—C10—C9116.56 (12)C17—C18—H18119.7
C11—C10—H10A108.2C20—C19—C18119.70 (13)
C9—C10—H10A108.2C20—C19—H19120.2
C11—C10—H10B108.2C18—C19—H19120.1
C9—C10—H10B108.2C19—C20—C21120.16 (14)
H10A—C10—H10B107.3C19—C20—H20119.9
C10—C11—C12116.04 (14)C21—C20—H20119.9
C10—C11—H11A108.3C20—C21—C16120.63 (13)
C12—C11—H11A108.3C20—C21—H21119.7
C10—C11—H11B108.3C16—C21—H21119.7
C12—C11—H11B108.3C15—N1—C1118.73 (10)
N1—C1—C2—C3−178.99 (12)C10—C11—C12—C13−98.63 (17)
C6—C1—C2—C30.70 (19)C11—C12—C13—C1470.55 (19)
C1—C2—C3—C4−0.6 (2)C12—C13—C14—C15−80.42 (17)
C2—C3—C4—C50.0 (2)C7—C8—C15—N10.29 (18)
C2—C3—C4—Cl1179.69 (11)C9—C8—C15—N1−178.45 (11)
C3—C4—C5—C60.7 (2)C7—C8—C15—C14−179.14 (11)
Cl1—C4—C5—C6−179.07 (9)C9—C8—C15—C142.13 (18)
C4—C5—C6—C1−0.59 (18)C13—C14—C15—N1−96.60 (14)
C4—C5—C6—C7178.98 (11)C13—C14—C15—C882.88 (16)
N1—C1—C6—C5179.60 (10)C8—C7—C16—C17103.88 (15)
C2—C1—C6—C5−0.07 (17)C6—C7—C16—C17−75.90 (16)
N1—C1—C6—C70.00 (17)C8—C7—C16—C21−79.21 (16)
C2—C1—C6—C7−179.67 (11)C6—C7—C16—C21101.02 (14)
C5—C6—C7—C8−179.10 (11)C21—C16—C17—C181.2 (2)
C1—C6—C7—C80.48 (16)C7—C16—C17—C18178.19 (15)
C5—C6—C7—C160.69 (17)C16—C17—C18—C19−0.6 (3)
C1—C6—C7—C16−179.74 (10)C17—C18—C19—C20−0.5 (3)
C6—C7—C8—C15−0.62 (17)C18—C19—C20—C211.0 (3)
C16—C7—C8—C15179.61 (10)C19—C20—C21—C16−0.3 (2)
C6—C7—C8—C9178.09 (11)C17—C16—C21—C20−0.8 (2)
C16—C7—C8—C9−1.68 (18)C7—C16—C21—C20−177.74 (13)
C7—C8—C9—C1091.27 (15)C8—C15—N1—C10.19 (18)
C15—C8—C9—C10−90.04 (15)C14—C15—N1—C1179.66 (10)
C8—C9—C10—C1146.24 (18)C6—C1—N1—C15−0.33 (18)
C9—C10—C11—C1259.62 (18)C2—C1—N1—C15179.34 (11)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2449).

References

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  • Doube, D., Blouin, M., Brideau, C., Chan, C., Desmarais, S., Eithier, D., Falgueyert, J. P., Friesen, R. W., Girrard, M., Girrard, J., Tagari, P. & Yang, R. N. (1998). Bioorg. Med. Chem. Lett.8, 1255–1260. [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Kalluraya, B. & Sreenivasa, S. (1998). Il Farmaco, 53, 399–404. [PubMed]
  • Maguire, M. P., Sheets, K. R., Mevety, K., Spada, A. P. & Ziberstein, A. (1994). J. Med. Chem.37, 2129–2137. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Stoe & Cie (2002). X-AREA, X-RED and X-SHAPE Stoe & Cie, Darmstadt, Germany.

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