Literature DB >> 21587992

(2E)-1-(6-Chloro-2-methyl-4-phenyl-quinolin-3-yl)-3-phenyl-prop-2-en-1-one.

A J Viji, S Sarveswari, V Vijayakumar, Kong Wai Tan, Edward R T Tiekink.   

Abstract

In the title compound, C(25)H(18)ClNO, the conformation about the C=C double bond is E. Significant twists are evident in the mol-ecule, with the benzene ring forming a dihedral angle of 53.92 (11)° with the quinolinyl residue. Further, the chalcone residue is approximately perpendicular to the quinolinyl residue [C(q)-C(q)-C(c)-O(c) torsion angle = -104.5 (3)°, where q = quinolinyl and c = chalcone]. In the crystal, the presence of C-H⋯O and C-H⋯π inter-actions leads to supra-molecular layers lying parallel to (02).

Entities:  

Year:  2010        PMID： 21587992      PMCID： PMC3006996          DOI： 10.1107/S160053681002386X

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


Related literature

For the biological activity of quinoline derivatives, see: Campbell et al. (1998 ▶). For the biological activity of chalcone derivatives, see: Chen et al. (2001 ▶); Zi & Simoneau (2005 ▶). For a related structure, see: Prasath et al. (2010 ▶).

Experimental

Crystal data

C25H18ClNO M = 383.85 Monoclinic, a = 9.9250 (9) Å b = 11.1001 (9) Å c = 17.4651 (15) Å β = 97.250 (1)° V = 1908.7 (3) Å3 Z = 4 Mo Kα radiation μ = 0.22 mm−1 T = 100 K 0.46 × 0.30 × 0.26 mm

Data collection

Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.536, T max = 1.000 16152 measured reflections 3948 independent reflections 3030 reflections with I > 2σ(I) R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.065 wR(F 2) = 0.188 S = 1.09 3948 reflections 254 parameters H-atom parameters constrained Δρmax = 0.85 e Å−3 Δρmin = −0.49 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002386X/hb5510sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053681002386X/hb5510Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C25H18ClNOF(000) = 800
Mr = 383.85Dx = 1.336 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4382 reflections
a = 9.9250 (9) Åθ = 2.2–28.1°
b = 11.1001 (9) ŵ = 0.22 mm−1
c = 17.4651 (15) ÅT = 100 K
β = 97.250 (1)°Block, colourless
V = 1908.7 (3) Å30.46 × 0.30 × 0.26 mm
Z = 4
Bruker SMART APEX CCD diffractometer3948 independent reflections
Radiation source: fine-focus sealed tube3030 reflections with I > 2σ(I)
graphiteRint = 0.079
ω scansθmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.536, Tmax = 1.000k = −13→13
16152 measured reflectionsl = −21→21
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.0925P)2 + 1.6015P] where P = (Fo2 + 2Fc2)/3
3948 reflections(Δ/σ)max < 0.001
254 parametersΔρmax = 0.85 e Å−3
0 restraintsΔρmin = −0.49 e Å−3
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl10.10119 (8)−0.00729 (6)0.39598 (4)0.0310 (2)
O10.13396 (19)0.68284 (16)0.58922 (12)0.0270 (5)
N10.3459 (2)0.4751 (2)0.42881 (14)0.0225 (5)
C10.4920 (3)0.5159 (2)0.77131 (17)0.0218 (6)
C20.4665 (3)0.5785 (2)0.83726 (17)0.0254 (6)
H20.39270.63350.83430.031*
C30.5471 (3)0.5616 (2)0.90671 (18)0.0275 (6)
H30.52780.60400.95130.033*
C40.6565 (3)0.4825 (2)0.91160 (18)0.0284 (7)
H40.71180.47060.95950.034*
C50.6847 (3)0.4212 (2)0.84662 (18)0.0291 (7)
H50.75990.36770.84970.035*
C60.6033 (3)0.4376 (2)0.77700 (17)0.0254 (6)
H60.62330.39520.73250.030*
C70.4062 (3)0.5249 (2)0.69742 (17)0.0219 (6)
H70.43260.47810.65620.026*
C80.2941 (3)0.5922 (2)0.68141 (17)0.0232 (6)
H80.26330.63650.72240.028*
C90.2165 (3)0.6014 (2)0.60506 (17)0.0218 (6)
C100.2406 (3)0.5114 (2)0.54359 (16)0.0196 (6)
C110.1878 (2)0.3965 (2)0.54427 (16)0.0196 (6)
C120.2102 (2)0.3183 (2)0.48211 (16)0.0192 (6)
C130.1502 (3)0.2022 (2)0.47167 (16)0.0211 (6)
H130.09110.17350.50630.025*
C140.1783 (3)0.1328 (2)0.41150 (17)0.0237 (6)
C150.2654 (3)0.1713 (2)0.35909 (17)0.0255 (6)
H150.28480.11990.31840.031*
C160.3223 (3)0.2835 (2)0.36714 (17)0.0242 (6)
H160.38170.31000.33200.029*
C170.2931 (3)0.3600 (2)0.42726 (16)0.0206 (6)
C180.3167 (3)0.5479 (2)0.48365 (17)0.0215 (6)
C190.3681 (3)0.6752 (2)0.48052 (18)0.0269 (6)
H19A0.43660.67940.44480.040*
H19B0.40880.70010.53210.040*
H19C0.29230.72900.46260.040*
C200.1112 (3)0.3561 (2)0.60680 (16)0.0210 (6)
C21−0.0006 (3)0.4208 (2)0.62611 (17)0.0238 (6)
H21−0.03100.49000.59690.029*
C22−0.0675 (3)0.3855 (3)0.68711 (18)0.0288 (7)
H22−0.14270.43080.69990.035*
C23−0.0251 (3)0.2841 (3)0.72961 (18)0.0306 (7)
H23−0.06970.26070.77230.037*
C240.0828 (3)0.2169 (2)0.70960 (18)0.0293 (7)
H240.10990.14580.73770.035*
C250.1511 (3)0.2522 (2)0.64943 (17)0.0250 (6)
H250.22560.20590.63670.030*
U11U22U33U12U13U23
Cl10.0373 (4)0.0150 (3)0.0400 (5)−0.0062 (3)0.0013 (3)−0.0048 (3)
O10.0212 (10)0.0136 (9)0.0452 (13)0.0019 (7)0.0001 (9)−0.0028 (8)
N10.0180 (11)0.0158 (11)0.0339 (14)0.0000 (9)0.0036 (9)0.0010 (9)
C10.0213 (13)0.0120 (12)0.0325 (16)−0.0028 (10)0.0048 (11)0.0020 (10)
C20.0247 (14)0.0163 (13)0.0354 (17)0.0002 (10)0.0042 (12)−0.0017 (11)
C30.0313 (16)0.0166 (13)0.0342 (17)−0.0025 (11)0.0026 (12)−0.0023 (11)
C40.0320 (16)0.0165 (13)0.0348 (17)−0.0024 (11)−0.0034 (13)0.0032 (11)
C50.0248 (15)0.0170 (13)0.0442 (19)0.0037 (11)−0.0011 (13)0.0019 (12)
C60.0255 (14)0.0172 (13)0.0340 (17)0.0015 (11)0.0060 (12)−0.0009 (11)
C70.0221 (14)0.0118 (11)0.0326 (16)−0.0023 (10)0.0070 (11)−0.0002 (11)
C80.0245 (14)0.0155 (12)0.0302 (16)0.0010 (10)0.0056 (11)−0.0036 (11)
C90.0162 (13)0.0122 (12)0.0371 (16)−0.0043 (10)0.0038 (11)−0.0005 (11)
C100.0153 (12)0.0151 (12)0.0279 (15)0.0016 (10)0.0004 (10)0.0016 (10)
C110.0126 (12)0.0154 (12)0.0298 (15)0.0007 (9)−0.0014 (10)0.0019 (10)
C120.0115 (12)0.0158 (12)0.0298 (15)0.0020 (9)0.0005 (10)0.0012 (10)
C130.0156 (12)0.0153 (12)0.0320 (16)0.0011 (10)0.0018 (11)0.0017 (11)
C140.0237 (14)0.0134 (12)0.0326 (16)0.0009 (10)−0.0023 (11)0.0009 (11)
C150.0283 (15)0.0171 (13)0.0310 (16)0.0054 (11)0.0035 (12)−0.0025 (11)
C160.0196 (13)0.0209 (13)0.0324 (16)0.0011 (11)0.0039 (11)0.0009 (11)
C170.0139 (12)0.0148 (12)0.0329 (16)0.0013 (9)0.0017 (10)0.0014 (11)
C180.0163 (13)0.0143 (12)0.0332 (16)−0.0002 (10)0.0002 (11)0.0014 (11)
C190.0246 (14)0.0149 (13)0.0416 (18)−0.0036 (11)0.0059 (12)0.0009 (12)
C200.0191 (13)0.0138 (12)0.0294 (15)−0.0042 (9)0.0003 (11)−0.0011 (10)
C210.0182 (13)0.0177 (13)0.0348 (17)−0.0018 (10)0.0013 (11)−0.0017 (11)
C220.0206 (14)0.0254 (14)0.0409 (18)−0.0062 (11)0.0066 (12)−0.0082 (13)
C230.0322 (16)0.0280 (15)0.0329 (17)−0.0155 (13)0.0085 (13)−0.0038 (12)
C240.0374 (17)0.0172 (13)0.0319 (17)−0.0087 (12)−0.0007 (13)0.0029 (12)
C250.0273 (14)0.0134 (12)0.0334 (17)−0.0018 (10)0.0000 (12)−0.0012 (11)
Cl1—C141.739 (3)C12—C171.417 (4)
O1—C91.228 (3)C12—C131.422 (3)
N1—C181.314 (4)C13—C141.360 (4)
N1—C171.379 (3)C13—H130.9500
C1—C21.396 (4)C14—C151.403 (4)
C1—C61.399 (4)C15—C161.368 (4)
C1—C71.457 (4)C15—H150.9500
C2—C31.379 (4)C16—C171.409 (4)
C2—H20.9500C16—H160.9500
C3—C41.391 (4)C18—C191.506 (3)
C3—H30.9500C19—H19A0.9800
C4—C51.382 (4)C19—H19B0.9800
C4—H40.9500C19—H19C0.9800
C5—C61.384 (4)C20—C211.399 (4)
C5—H50.9500C20—C251.402 (4)
C6—H60.9500C21—C221.381 (4)
C7—C81.340 (4)C21—H210.9500
C7—H70.9500C22—C231.384 (4)
C8—C91.457 (4)C22—H220.9500
C8—H80.9500C23—C241.385 (4)
C9—C101.508 (4)C23—H230.9500
C10—C111.380 (3)C24—C251.377 (4)
C10—C181.425 (4)C24—H240.9500
C11—C121.429 (4)C25—H250.9500
C11—C201.477 (4)
C18—N1—C17117.8 (2)C13—C14—C15122.3 (2)
C2—C1—C6118.3 (3)C13—C14—Cl1119.8 (2)
C2—C1—C7123.4 (2)C15—C14—Cl1117.8 (2)
C6—C1—C7118.3 (3)C16—C15—C14119.4 (3)
C3—C2—C1120.9 (3)C16—C15—H15120.3
C3—C2—H2119.6C14—C15—H15120.3
C1—C2—H2119.6C15—C16—C17120.3 (3)
C2—C3—C4120.1 (3)C15—C16—H16119.8
C2—C3—H3119.9C17—C16—H16119.8
C4—C3—H3119.9N1—C17—C16117.3 (2)
C5—C4—C3119.9 (3)N1—C17—C12122.7 (2)
C5—C4—H4120.1C16—C17—C12119.9 (2)
C3—C4—H4120.1N1—C18—C10123.1 (2)
C4—C5—C6120.0 (3)N1—C18—C19116.4 (3)
C4—C5—H5120.0C10—C18—C19120.5 (2)
C6—C5—H5120.0C18—C19—H19A109.5
C5—C6—C1120.8 (3)C18—C19—H19B109.5
C5—C6—H6119.6H19A—C19—H19B109.5
C1—C6—H6119.6C18—C19—H19C109.5
C8—C7—C1126.9 (3)H19A—C19—H19C109.5
C8—C7—H7116.6H19B—C19—H19C109.5
C1—C7—H7116.6C21—C20—C25118.3 (3)
C7—C8—C9124.0 (3)C21—C20—C11121.4 (2)
C7—C8—H8118.0C25—C20—C11120.4 (2)
C9—C8—H8118.0C22—C21—C20120.9 (3)
O1—C9—C8121.3 (2)C22—C21—H21119.6
O1—C9—C10119.3 (3)C20—C21—H21119.6
C8—C9—C10119.4 (2)C21—C22—C23120.1 (3)
C11—C10—C18120.5 (2)C21—C22—H22120.0
C11—C10—C9120.8 (2)C23—C22—H22120.0
C18—C10—C9118.7 (2)C22—C23—C24119.7 (3)
C10—C11—C12117.3 (2)C22—C23—H23120.2
C10—C11—C20121.2 (2)C24—C23—H23120.2
C12—C11—C20121.5 (2)C25—C24—C23120.7 (3)
C17—C12—C13118.6 (2)C25—C24—H24119.7
C17—C12—C11118.3 (2)C23—C24—H24119.7
C13—C12—C11123.0 (2)C24—C25—C20120.4 (3)
C14—C13—C12119.3 (3)C24—C25—H25119.8
C14—C13—H13120.4C20—C25—H25119.8
C12—C13—H13120.4
C6—C1—C2—C3−1.5 (4)C13—C14—C15—C16−1.5 (4)
C7—C1—C2—C3176.5 (3)Cl1—C14—C15—C16176.6 (2)
C1—C2—C3—C40.8 (4)C14—C15—C16—C17−0.3 (4)
C2—C3—C4—C50.2 (4)C18—N1—C17—C16178.5 (2)
C3—C4—C5—C6−0.6 (4)C18—N1—C17—C12−0.3 (4)
C4—C5—C6—C1−0.1 (4)C15—C16—C17—N1−175.5 (2)
C2—C1—C6—C51.1 (4)C15—C16—C17—C123.3 (4)
C7—C1—C6—C5−177.0 (3)C13—C12—C17—N1174.2 (2)
C2—C1—C7—C80.2 (4)C11—C12—C17—N1−4.0 (4)
C6—C1—C7—C8178.2 (3)C13—C12—C17—C16−4.5 (4)
C1—C7—C8—C9176.9 (2)C11—C12—C17—C16177.2 (2)
C7—C8—C9—O1−163.7 (3)C17—N1—C18—C104.0 (4)
C7—C8—C9—C1014.7 (4)C17—N1—C18—C19−176.0 (2)
O1—C9—C10—C11−104.5 (3)C11—C10—C18—N1−3.2 (4)
C8—C9—C10—C1177.1 (3)C9—C10—C18—N1178.2 (2)
O1—C9—C10—C1874.1 (3)C11—C10—C18—C19176.8 (2)
C8—C9—C10—C18−104.3 (3)C9—C10—C18—C19−1.9 (4)
C18—C10—C11—C12−1.3 (4)C10—C11—C20—C2154.1 (4)
C9—C10—C11—C12177.3 (2)C12—C11—C20—C21−126.0 (3)
C18—C10—C11—C20178.7 (2)C10—C11—C20—C25−124.8 (3)
C9—C10—C11—C20−2.7 (4)C12—C11—C20—C2555.2 (3)
C10—C11—C12—C174.6 (3)C25—C20—C21—C222.0 (4)
C20—C11—C12—C17−175.4 (2)C11—C20—C21—C22−176.9 (2)
C10—C11—C12—C13−173.6 (2)C20—C21—C22—C23−0.7 (4)
C20—C11—C12—C136.5 (4)C21—C22—C23—C24−1.4 (4)
C17—C12—C13—C142.7 (4)C22—C23—C24—C252.1 (4)
C11—C12—C13—C14−179.1 (2)C23—C24—C25—C20−0.8 (4)
C12—C13—C14—C150.3 (4)C21—C20—C25—C24−1.2 (4)
C12—C13—C14—Cl1−177.80 (19)C11—C20—C25—C24177.6 (2)
Cg1 is the centroid of the N1,C10–C12,C17,C18 ring.
D—H···AD—HH···AD···AD—H···A
C5—H5···O1i0.952.483.315 (3)146
C21—H21···Cg1ii0.952.713.459 (3)137
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1,C10–C12,C17,C18 ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C5—H5⋯O1i0.952.483.315 (3)146
C21—H21⋯Cg1ii0.952.713.459 (3)137

Symmetry codes: (i) ; (ii) .

  5 in total

1.  A short history of SHELX.

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

2.  Flavokawain A, a novel chalcone from kava extract, induces apoptosis in bladder cancer cells by involvement of Bax protein-dependent and mitochondria-dependent apoptotic pathway and suppresses tumor growth in mice.

Authors:  Xiaolin Zi; Anne R Simoneau
Journal:  Cancer Res       Date:  2005-04-15       Impact factor: 12.701

3.  Synthesis and antibacterial evaluation of certain quinolone derivatives.

Authors:  Y L Chen; K C Fang; J Y Sheu; S L Hsu; C C Tzeng
Journal:  J Med Chem       Date:  2001-07-05       Impact factor: 7.446

4.  2,4-Diamino-6,7-dimethoxyquinoline derivatives as alpha 1-adrenoceptor antagonists and antihypertensive agents.

Authors:  S F Campbell; J D Hardstone; M J Palmer
Journal:  J Med Chem       Date:  1988-05       Impact factor: 7.446

5.  (2E)-3-(4-Bromo-phen-yl)-1-(2-methyl-4-phenyl-3-quinol-yl)prop-2-en-1-one.

Authors:  R Prasath; S Sarveswari; V Vijayakumar; T Narasimhamurthy; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-04-17
  5 in total
  2 in total

1.  3-Acetyl-2-methyl-4-phenyl-quinolin-1-ium chloride.

Authors:  K Kiran; S Sarveswari; V Vijayakumar; Kang Wai Tan; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-07-14

2.  1-[6-Chloro-4-(2-chloro-phen-yl)-2-methyl-3-quinol-yl]ethanone.

Authors:  B Preeti; S Sarveswari; V Vijayakumar; Kang Wai Tan; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-07-14
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.