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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o353–o354.
Published online 2010 January 13. doi:  10.1107/S1600536810000784
PMCID: PMC2979743

(E)-1-(6-Chloro-2-methyl-4-phenyl-3-quinol­yl)-3-(2-methoxy­phen­yl)prop-2-en-1-one

Abstract

In the title compound, C26H20ClNO2, the quinoline ring system and the methoxy­phenyl ring form dihedral angles of 69.97 (6) and 22.10 (10)°, respectively, with the propenone linkage. The 4-phenyl ring substituent on the quinoline ring system is oriented at a dihedral angle of 66.47 (3)°. In the crystal, mol­ecules exist as C—H(...)O hydrogen-bonded dimers. The structure is further stabilized by C—H(...)π inter­actions.

Related literature

For background details and the biological activity of quinolines, see: Michael (1997 [triangle]); Markees et al. (1970 [triangle]); Kalluraya & Sreenivasa (1998 [triangle]); Chen et al. (2001 [triangle]). For the biological activity of chalcones, see: Dimmock et al. (1999 [triangle]); Zi & Simoneau (2005 [triangle]). For related structures, see: Loh et al. (2009a [triangle],b [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o353-scheme1.jpg

Experimental

Crystal data

  • C26H20ClNO2
  • M r = 413.88
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o353-efi1.jpg
  • a = 15.1154 (2) Å
  • b = 15.4655 (2) Å
  • c = 17.2400 (2) Å
  • β = 104.418 (1)°
  • V = 3903.22 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.22 mm−1
  • T = 100 K
  • 0.39 × 0.25 × 0.19 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.919, T max = 0.960
  • 30753 measured reflections
  • 8197 independent reflections
  • 5864 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.136
  • S = 1.06
  • 8197 reflections
  • 273 parameters
  • H-atom parameters constrained
  • Δρmax = 0.54 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810000784/ci5015sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000784/ci5015Isup2.hkl

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

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant No. 1001/PFIZIK/811012. WSL thanks the Malaysian government and USM for the award of the post of Assistant Research Officer under Research University Golden Goose grant No. 1001/PFIZIK/811012. VV is grateful to DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

supplementary crystallographic information

Comment

Quinoline and its derivatives are very important compounds because of their wide occurrence in natural products (Michael, 1997) and biologically active compounds (Markees et al., 1970). A large variety of quinolines have interesting physiological activities and found attractive applications as pharmaceuticals, agrochemicals and as synthetic building blocks (Kalluraya & Sreenivasa, 1998; Chen et al., 2001). The chalcones are open chain flavonoids, possessing a variety of biological activities, including antioxidant, anti-inflammation, antimicrobial, antiprotozoal, antiulcer, as well as other activities (Dimmock et al., 1999). More importantly, chalcones have shown several anticancer activities as inhibitors of cancer cell proliferation, carcinogenesis and metastasis (Zi & Simoneau, 2005).

In the molecule of the title compound (Fig. 1), the quinoline ring system (C1–C9/N1) is approximately planar with a maximum deviation of 0.065 (1) Å for atom C9. The mean plane of the quinoline ring system forms a dihedral angle of 66.47 (3)° with the C10-C15 phenyl ring. The C1–C9/N1 and C19-C24 planes form dihedral angles of 69.97 (6) and 22.10 (10)°, respectively, with the O1/C16-C18 plane. Bond lengths (Allen et al., 1987) and angles are within the normal range and are comparable to closely related structures (Loh et al., 2009a; Loh et al., 2009b).

In the crystal (Fig. 2), pairs of neighbouring molecules are arranged into dimers by pairs of intermolecular C12—H12A···O1 hydrogen bonds. The crystal structure is further stabilized by C—H···π interactions (Table 1), involving C2–C7 (centroid Cg1) and N1/C1/C2/C7-C9 (centroid Cg2) rings.

Experimental

A mixture of 3-acetyl-6-chloro-2-methyl-4-phenylquinoline (2.95 g, 0.01 mol), 2-methoxybenzaldehyde (1.36 g, 0.01 mol) and a catalytic amount of KOH in distilled ethanol was stirred for 12 h. The resulting mixture was concentrated to remove the ethanol and then poured onto ice and neutralized with diluted acetic acid. The resultant solid was filtered, dried and purified by column chromatography using a 1:1 mixture of ethyl acetate and petroleum ether (m.p. 403–405 K, yield: 68%).

Refinement

H atoms were positioned geometrically [C–H = 0.93 or 0.96 Å] and were refined using a riding model, with Uiso(H) = 1.2-1.5Ueq(C). A rotating group model was applied to the methyl groups.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
Fig. 2.
The crystal packing of the title compound, viewed approximately along the b axis, showing the dimers. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Crystal data

C26H20ClNO2F(000) = 1728
Mr = 413.88Dx = 1.409 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 7486 reflections
a = 15.1154 (2) Åθ = 2.4–31.5°
b = 15.4655 (2) ŵ = 0.22 mm1
c = 17.2400 (2) ÅT = 100 K
β = 104.418 (1)°Block, yellow
V = 3903.22 (9) Å30.39 × 0.25 × 0.19 mm
Z = 8

Data collection

Bruker SMART APEXII CCD area-detector diffractometer8197 independent reflections
Radiation source: fine-focus sealed tube5864 reflections with I > 2σ(I)
graphiteRint = 0.039
[var phi] and ω scansθmax = 34.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −20→24
Tmin = 0.919, Tmax = 0.960k = −24→19
30753 measured reflectionsl = −27→27

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0625P)2 + 0.7227P] where P = (Fo2 + 2Fc2)/3
8197 reflections(Δ/σ)max = 0.001
273 parametersΔρmax = 0.54 e Å3
0 restraintsΔρmin = −0.31 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
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
Cl10.02177 (2)1.01758 (2)0.635395 (19)0.01901 (8)
O10.27571 (6)0.58953 (6)0.86651 (5)0.0176 (2)
O2−0.04599 (6)0.49228 (6)0.58651 (5)0.0182 (2)
N10.23373 (7)0.70354 (7)0.61280 (6)0.0132 (2)
C10.24441 (8)0.64331 (8)0.66867 (7)0.0119 (2)
C20.18686 (8)0.77723 (8)0.62237 (7)0.0118 (2)
C30.17164 (9)0.83936 (8)0.55976 (7)0.0140 (2)
H3A0.19480.82990.51530.017*
C40.12304 (9)0.91308 (8)0.56457 (7)0.0147 (2)
H4A0.11300.95380.52360.018*
C50.08838 (8)0.92650 (8)0.63233 (7)0.0137 (2)
C60.10437 (8)0.87006 (8)0.69522 (7)0.0130 (2)
H6A0.08260.88180.74000.016*
C70.15466 (8)0.79326 (8)0.69143 (7)0.0114 (2)
C80.17037 (8)0.72900 (8)0.75300 (7)0.0113 (2)
C90.21100 (8)0.65250 (8)0.73916 (7)0.0117 (2)
C100.14444 (8)0.74686 (8)0.82932 (7)0.0126 (2)
C110.18819 (9)0.81414 (9)0.87804 (8)0.0184 (3)
H11A0.23230.84680.86220.022*
C120.16655 (11)0.83282 (10)0.94971 (8)0.0234 (3)
H12A0.19660.87740.98190.028*
C130.10036 (10)0.78525 (10)0.97343 (8)0.0236 (3)
H13A0.08530.79831.02120.028*
C140.05658 (9)0.71812 (10)0.92586 (8)0.0213 (3)
H14A0.01220.68600.94190.026*
C150.07867 (9)0.69836 (9)0.85395 (7)0.0166 (2)
H15A0.04950.65280.82250.020*
C160.22442 (8)0.57996 (8)0.79974 (7)0.0125 (2)
C170.17554 (9)0.49843 (8)0.77583 (7)0.0144 (2)
H17A0.19080.45090.80950.017*
C180.10990 (9)0.48907 (8)0.70786 (7)0.0137 (2)
H18A0.09290.53840.67690.016*
C190.06258 (8)0.40889 (8)0.67781 (7)0.0135 (2)
C200.09598 (9)0.32817 (8)0.70747 (8)0.0161 (2)
H20A0.14930.32530.74840.019*
C210.05186 (9)0.25228 (9)0.67757 (8)0.0186 (3)
H21A0.07580.19900.69740.022*
C22−0.02865 (9)0.25684 (9)0.61751 (8)0.0193 (3)
H22A−0.05950.20620.59830.023*
C23−0.06371 (9)0.33563 (9)0.58583 (8)0.0171 (3)
H23A−0.11750.33770.54540.021*
C24−0.01789 (9)0.41163 (8)0.61490 (7)0.0148 (2)
C250.29908 (9)0.56529 (8)0.65696 (8)0.0170 (2)
H25A0.32730.57580.61370.026*
H25B0.25940.51600.64450.026*
H25C0.34540.55420.70520.026*
C26−0.12419 (10)0.49727 (10)0.51992 (8)0.0213 (3)
H26A−0.13480.55640.50340.032*
H26B−0.17670.47520.53530.032*
H26C−0.11360.46360.47630.032*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.01956 (16)0.01561 (16)0.02069 (15)0.00653 (12)0.00279 (12)0.00098 (11)
O10.0204 (5)0.0172 (5)0.0129 (4)0.0012 (4)−0.0004 (3)−0.0009 (3)
O20.0176 (5)0.0162 (5)0.0172 (4)0.0006 (4)−0.0022 (4)0.0005 (3)
N10.0144 (5)0.0130 (5)0.0124 (4)0.0001 (4)0.0039 (4)−0.0009 (4)
C10.0120 (5)0.0122 (6)0.0117 (5)−0.0003 (4)0.0030 (4)−0.0017 (4)
C20.0109 (5)0.0123 (5)0.0119 (5)−0.0004 (4)0.0026 (4)−0.0004 (4)
C30.0148 (6)0.0156 (6)0.0112 (5)−0.0014 (4)0.0025 (4)0.0004 (4)
C40.0158 (6)0.0147 (6)0.0125 (5)−0.0006 (5)0.0013 (4)0.0014 (4)
C50.0130 (6)0.0110 (5)0.0155 (5)0.0003 (4)0.0008 (4)−0.0005 (4)
C60.0139 (5)0.0135 (6)0.0118 (5)0.0002 (4)0.0034 (4)−0.0010 (4)
C70.0108 (5)0.0120 (6)0.0111 (5)−0.0003 (4)0.0021 (4)−0.0001 (4)
C80.0113 (5)0.0121 (5)0.0106 (5)−0.0017 (4)0.0028 (4)−0.0001 (4)
C90.0120 (5)0.0116 (5)0.0111 (5)−0.0007 (4)0.0022 (4)−0.0005 (4)
C100.0152 (6)0.0121 (5)0.0107 (5)0.0031 (4)0.0038 (4)0.0011 (4)
C110.0228 (7)0.0180 (6)0.0154 (5)−0.0025 (5)0.0069 (5)−0.0022 (5)
C120.0329 (8)0.0227 (7)0.0153 (6)0.0010 (6)0.0073 (6)−0.0046 (5)
C130.0293 (8)0.0305 (8)0.0135 (5)0.0091 (6)0.0103 (5)0.0023 (5)
C140.0206 (7)0.0282 (8)0.0186 (6)0.0042 (6)0.0116 (5)0.0059 (5)
C150.0170 (6)0.0179 (6)0.0157 (5)0.0009 (5)0.0054 (5)0.0019 (5)
C160.0132 (5)0.0132 (6)0.0116 (5)0.0015 (4)0.0042 (4)−0.0001 (4)
C170.0180 (6)0.0119 (6)0.0139 (5)0.0003 (4)0.0052 (5)0.0012 (4)
C180.0152 (6)0.0129 (6)0.0136 (5)−0.0001 (4)0.0047 (4)−0.0003 (4)
C190.0126 (5)0.0155 (6)0.0132 (5)−0.0009 (4)0.0047 (4)−0.0006 (4)
C200.0140 (6)0.0166 (6)0.0170 (6)0.0000 (5)0.0026 (5)−0.0017 (5)
C210.0200 (6)0.0130 (6)0.0218 (6)0.0005 (5)0.0036 (5)−0.0012 (5)
C220.0215 (7)0.0163 (6)0.0201 (6)−0.0037 (5)0.0052 (5)−0.0041 (5)
C230.0156 (6)0.0204 (6)0.0150 (5)−0.0024 (5)0.0032 (5)−0.0031 (5)
C240.0144 (6)0.0167 (6)0.0140 (5)0.0004 (5)0.0048 (4)−0.0016 (4)
C250.0193 (6)0.0160 (6)0.0168 (6)0.0046 (5)0.0065 (5)0.0005 (5)
C260.0179 (7)0.0245 (7)0.0178 (6)0.0014 (5)−0.0025 (5)0.0019 (5)

Geometric parameters (Å, °)

Cl1—C51.7397 (13)C13—C141.385 (2)
O1—C161.2262 (14)C13—H13A0.93
O2—C241.3683 (15)C14—C151.3956 (17)
O2—C261.4302 (16)C14—H14A0.93
N1—C11.3207 (15)C15—H15A0.93
N1—C21.3733 (15)C16—C171.4678 (18)
C1—C91.4344 (16)C17—C181.3414 (17)
C1—C251.5042 (17)C17—H17A0.93
C2—C71.4158 (16)C18—C191.4606 (18)
C2—C31.4205 (17)C18—H18A0.93
C3—C41.3700 (18)C19—C201.3951 (18)
C3—H3A0.93C19—C241.4144 (18)
C4—C51.4098 (17)C20—C211.3845 (18)
C4—H4A0.93C20—H20A0.93
C5—C61.3657 (16)C21—C221.3895 (18)
C6—C71.4204 (17)C21—H21A0.93
C6—H6A0.93C22—C231.3855 (19)
C7—C81.4302 (16)C22—H22A0.93
C8—C91.3808 (17)C23—C241.3926 (18)
C8—C101.4893 (16)C23—H23A0.93
C9—C161.5116 (17)C25—H25A0.96
C10—C151.3934 (18)C25—H25B0.96
C10—C111.3960 (18)C25—H25C0.96
C11—C121.3851 (18)C26—H26A0.96
C11—H11A0.93C26—H26B0.96
C12—C131.383 (2)C26—H26C0.96
C12—H12A0.93
C24—O2—C26117.21 (10)C15—C14—H14A119.8
C1—N1—C2118.08 (10)C10—C15—C14119.97 (12)
N1—C1—C9122.90 (11)C10—C15—H15A120.0
N1—C1—C25116.07 (10)C14—C15—H15A120.0
C9—C1—C25120.94 (10)O1—C16—C17121.58 (11)
N1—C2—C7122.82 (11)O1—C16—C9120.26 (11)
N1—C2—C3117.44 (10)C17—C16—C9118.16 (10)
C7—C2—C3119.74 (11)C18—C17—C16123.30 (11)
C4—C3—C2120.32 (11)C18—C17—H17A118.3
C4—C3—H3A119.8C16—C17—H17A118.3
C2—C3—H3A119.8C17—C18—C19126.29 (12)
C3—C4—C5119.23 (11)C17—C18—H18A116.9
C3—C4—H4A120.4C19—C18—H18A116.9
C5—C4—H4A120.4C20—C19—C24118.13 (11)
C6—C5—C4122.34 (11)C20—C19—C18121.94 (11)
C6—C5—Cl1118.87 (10)C24—C19—C18119.89 (11)
C4—C5—Cl1118.79 (9)C21—C20—C19121.69 (12)
C5—C6—C7119.27 (11)C21—C20—H20A119.2
C5—C6—H6A120.4C19—C20—H20A119.2
C7—C6—H6A120.4C20—C21—C22119.06 (12)
C2—C7—C6119.02 (10)C20—C21—H21A120.5
C2—C7—C8118.30 (11)C22—C21—H21A120.5
C6—C7—C8122.60 (11)C23—C22—C21121.09 (12)
C9—C8—C7117.77 (10)C23—C22—H22A119.5
C9—C8—C10122.53 (10)C21—C22—H22A119.5
C7—C8—C10119.68 (11)C22—C23—C24119.56 (12)
C8—C9—C1119.79 (10)C22—C23—H23A120.2
C8—C9—C16120.36 (10)C24—C23—H23A120.2
C1—C9—C16119.79 (10)O2—C24—C23123.95 (11)
C15—C10—C11119.01 (11)O2—C24—C19115.63 (11)
C15—C10—C8122.28 (11)C23—C24—C19120.42 (12)
C11—C10—C8118.71 (11)C1—C25—H25A109.5
C12—C11—C10120.69 (13)C1—C25—H25B109.5
C12—C11—H11A119.7H25A—C25—H25B109.5
C10—C11—H11A119.7C1—C25—H25C109.5
C13—C12—C11120.11 (13)H25A—C25—H25C109.5
C13—C12—H12A119.9H25B—C25—H25C109.5
C11—C12—H12A119.9O2—C26—H26A109.5
C12—C13—C14119.85 (12)O2—C26—H26B109.5
C12—C13—H13A120.1H26A—C26—H26B109.5
C14—C13—H13A120.1O2—C26—H26C109.5
C13—C14—C15120.36 (13)H26A—C26—H26C109.5
C13—C14—H14A119.8H26B—C26—H26C109.5
C2—N1—C1—C9−1.36 (17)C7—C8—C10—C11−63.24 (16)
C2—N1—C1—C25−177.88 (10)C15—C10—C11—C12−0.21 (19)
C1—N1—C2—C73.89 (17)C8—C10—C11—C12−179.71 (12)
C1—N1—C2—C3−176.69 (11)C10—C11—C12—C13−0.6 (2)
N1—C2—C3—C4178.10 (11)C11—C12—C13—C140.9 (2)
C7—C2—C3—C4−2.46 (18)C12—C13—C14—C15−0.2 (2)
C2—C3—C4—C50.00 (18)C11—C10—C15—C140.85 (19)
C3—C4—C5—C62.54 (19)C8—C10—C15—C14−179.67 (11)
C3—C4—C5—Cl1−176.70 (10)C13—C14—C15—C10−0.6 (2)
C4—C5—C6—C7−2.50 (18)C8—C9—C16—O1−64.94 (16)
Cl1—C5—C6—C7176.75 (9)C1—C9—C16—O1112.20 (13)
N1—C2—C7—C6−178.11 (11)C8—C9—C16—C17115.85 (13)
C3—C2—C7—C62.48 (17)C1—C9—C16—C17−67.02 (15)
N1—C2—C7—C8−1.18 (17)O1—C16—C17—C18170.75 (12)
C3—C2—C7—C8179.42 (11)C9—C16—C17—C18−10.04 (18)
C5—C6—C7—C2−0.04 (17)C16—C17—C18—C19175.84 (12)
C5—C6—C7—C8−176.84 (11)C17—C18—C19—C20−15.8 (2)
C2—C7—C8—C9−4.05 (17)C17—C18—C19—C24166.47 (12)
C6—C7—C8—C9172.77 (11)C24—C19—C20—C21−0.80 (18)
C2—C7—C8—C10174.87 (11)C18—C19—C20—C21−178.61 (12)
C6—C7—C8—C10−8.31 (17)C19—C20—C21—C22−1.21 (19)
C7—C8—C9—C16.47 (17)C20—C21—C22—C231.8 (2)
C10—C8—C9—C1−172.42 (11)C21—C22—C23—C24−0.39 (19)
C7—C8—C9—C16−176.40 (10)C26—O2—C24—C23−3.77 (18)
C10—C8—C9—C164.71 (18)C26—O2—C24—C19176.59 (11)
N1—C1—C9—C8−3.94 (18)C22—C23—C24—O2178.69 (12)
C25—C1—C9—C8172.42 (11)C22—C23—C24—C19−1.69 (19)
N1—C1—C9—C16178.91 (11)C20—C19—C24—O2−178.09 (11)
C25—C1—C9—C16−4.73 (17)C18—C19—C24—O2−0.24 (17)
C9—C8—C10—C15−63.86 (17)C20—C19—C24—C232.26 (18)
C7—C8—C10—C15117.28 (13)C18—C19—C24—C23−179.89 (11)
C9—C8—C10—C11115.63 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C12—H12A···O1i0.932.593.2963 (16)133
C17—H17A···Cg1ii0.932.963.6617 (14)134
C20—H20A···Cg2ii0.932.853.6353 (14)143

Symmetry codes: (i) −x+1/2, −y+3/2, −z+2; (ii) x, −y−1, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5015).

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