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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3284.
Published online 2010 November 24. doi:  10.1107/S1600536810048026
PMCID: PMC3011764

(2E)-3-(4-Eth­oxy­phen­yl)-1-(2-methyl-4-phenyl­quinolin-3-yl)prop-2-en-1-one monohydrate

Abstract

The title hydrate, C27H23NO2·H2O, features an almost planar quinoline residue (r.m.s. deviation = 0.015 Å) with the benzene [dihedral angle = 63.80 (7) °] and chalcone [C—C—C—O torsion angle = −103.38 (18)°] substituents twisted significantly out of its plane. The configuration about the C=C bond [1.340 (2) Å] is E. In the crystal, mol­ecules related by the 21 symmetry operation are linked along the b axis via water mol­ecules that form O—H(...)Oc and O—H(...)Nq hydrogen bonds (c = carbonyl and q = quinoline). A C—H(...)O inter­action also occurs.

Related literature

For background to chalcones, see: Schröder et al. (1988 [triangle]); Schröder & Schröder (1990 [triangle]). For a related structure, see: Prasath et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3284-scheme1.jpg

Experimental

Crystal data

  • C27H23NO2·H2O
  • M r = 411.48
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3284-efi1.jpg
  • a = 17.4256 (4) Å
  • b = 7.6240 (2) Å
  • c = 18.4117 (4) Å
  • β = 116.957 (1)°
  • V = 2180.27 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.37 × 0.24 × 0.15 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1998 [triangle]) T min = 0.977, T max = 0.988
  • 29183 measured reflections
  • 4993 independent reflections
  • 3568 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.146
  • S = 1.05
  • 4993 reflections
  • 288 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and DIAMOND (Brandenburg, 2006 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048026/hb5746sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048026/hb5746Isup2.hkl

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

Acknowledgments

VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal). TN acknowledges the use of the X-ray CCD facility at the Indian Institute of Science, Bangalore, set up under the IRHPA DST programme.

supplementary crystallographic information

Comment

Chalcones are open-chain flavonoids in which two aromatic rings, jointed by a three carbon linker, are synthesized by chalcone synthetase from 3-malonyl-CoA and a starter CoA ester such as 4-coumaronyl-CoA in plants (Schröder et al., 1988). Chalcone synthetase functions as a key enzyme of flavonoid biosynthesis, using the similar substrates as stilbene synthetase (Schröder & Schröder, 1990). The title hydrate, (I), was investigated in continuation of structural studies of chalcones (Prasath et al., 2010).

With reference to least-squares plane through the quinoline residue in (I), Fig. 1, the phenyl ring is twisted and forms a dihedral angle of 63.80 (7) ° with it. Similarly, the chalcone residue is also twisted out of the plane as seen in the value of the C1—C2—C17—O1 torsion angle of -103.38 (18) °. There are discernible twists in the chalcone residue as seen in the value of the O1—C17—C18—C19 torsion angle of 6.8 (3) ° and especially C18—C19—C20—C21 of -168.50 (16) °. The configuration about the C18═ C19 bond [1.340 (2) Å] is E. The ethoxy group is lies in the plane of the benzene ring to which it is connected [C26—O2—C23—C22 = -3.7 (3) ° and C23—O2—C26—C27 = -178.30 (17) °].

The crystal packing is dominated by hydrogen bonds formed by the water molecule of crystallization. Thus, the carbonyl-O1 of one molecule is linked to a quinoline-N of another via O—H···O and O—H···N hydrogen bonds, Table 1. This results in the formation of a supramolecular chain with a helical topology along the b axis, Fig. 2. Chains are consolidated in the crystal packing by C—H···O contacts, Table 1.

Experimental

A mixture of 3-acetyl-2-methyl-4-phenylquinoline (2.6 g 0.01 M) and 4-ethoxybenzaldehyde (1.5 g 0.01 M) and a catalytic amount of KOH in distilled ethanol (50 ml) was stirred for about 24 h. The resulting mixture was concentrated to remove ethanol then poured onto ice and neutralized with dilute acetic acid. The resultant solid was filtered off, dried and purified by column chromatography using a 1:1 mixture of ethyl acetate and petroleum ether. Recrystallization was from acetone to yield colourless blocks; Yield: 64% and m. pt: 427–429 K.

Refinement

The C-bound H atoms were geometrically placed (C–H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The remaining H were located from a difference map and refined with O–H = 0.82±0.01 Å (with H1w···H2w = 1.36±0.015 Å), and with Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of (I) showing displacement ellipsoids at the 35% probability level.
Fig. 2.
A view of a supramolecular chain sustained by O—H···O and O—H···N hydrogen bonds shown as orange and blue dashed lines, respectively.

Crystal data

C27H23NO2·H2OF(000) = 872
Mr = 411.48Dx = 1.254 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9513 reflections
a = 17.4256 (4) Åθ = 2.2–29.5°
b = 7.6240 (2) ŵ = 0.08 mm1
c = 18.4117 (4) ÅT = 293 K
β = 116.957 (1)°Block, colourless
V = 2180.27 (9) Å30.37 × 0.24 × 0.15 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer4993 independent reflections
Radiation source: fine-focus sealed tube3568 reflections with I > 2σ(I)
graphiteRint = 0.033
ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)h = −22→22
Tmin = 0.977, Tmax = 0.988k = −9→8
29183 measured reflectionsl = −18→23

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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.065P)2 + 0.6319P] where P = (Fo2 + 2Fc2)/3
4993 reflections(Δ/σ)max = 0.001
288 parametersΔρmax = 0.25 e Å3
3 restraintsΔρmin = −0.19 e Å3

Special details

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.

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

xyzUiso*/Ueq
O10.25716 (8)0.36751 (17)0.84346 (7)0.0543 (3)
O20.50345 (8)−0.52976 (18)1.12587 (8)0.0590 (4)
N1−0.02026 (8)0.1867 (2)0.72578 (8)0.0466 (4)
C10.06079 (10)0.1951 (2)0.78155 (10)0.0414 (4)
C20.12999 (10)0.2106 (2)0.76061 (9)0.0366 (3)
C30.11343 (10)0.2195 (2)0.67992 (9)0.0362 (3)
C40.02593 (10)0.2109 (2)0.61876 (9)0.0392 (4)
C50.00012 (12)0.2155 (2)0.53384 (10)0.0500 (4)
H50.04160.22740.51550.060*
C6−0.08461 (13)0.2026 (3)0.47860 (11)0.0593 (5)
H6−0.10040.20670.42310.071*
C7−0.14798 (13)0.1831 (3)0.50494 (12)0.0631 (6)
H7−0.20550.17360.46680.076*
C8−0.12593 (12)0.1781 (3)0.58612 (12)0.0574 (5)
H8−0.16850.16490.60300.069*
C9−0.03862 (10)0.1928 (2)0.64478 (10)0.0431 (4)
C100.07655 (12)0.1904 (3)0.86890 (11)0.0568 (5)
H10A0.02250.19700.87090.085*
H10B0.11200.28810.89780.085*
H10C0.10520.08300.89370.085*
C110.18529 (10)0.2312 (2)0.65688 (9)0.0377 (4)
C120.19313 (12)0.3754 (3)0.61469 (10)0.0498 (4)
H120.15370.46680.60100.060*
C130.25941 (13)0.3837 (3)0.59282 (12)0.0581 (5)
H130.26420.48090.56460.070*
C140.31808 (12)0.2493 (3)0.61263 (11)0.0546 (5)
H140.36220.25500.59750.066*
C150.31119 (12)0.1063 (3)0.65488 (11)0.0526 (5)
H150.35120.01600.66880.063*
C160.24500 (11)0.0957 (2)0.67697 (10)0.0449 (4)
H160.2406−0.00180.70520.054*
C170.22121 (10)0.2250 (2)0.82790 (9)0.0378 (4)
C180.26143 (10)0.0642 (2)0.87161 (9)0.0434 (4)
H180.2325−0.04150.85270.052*
C190.33811 (10)0.0620 (2)0.93782 (9)0.0401 (4)
H190.36590.16940.95460.048*
C200.38267 (9)−0.0908 (2)0.98645 (9)0.0375 (4)
C210.45460 (10)−0.0704 (2)1.06181 (10)0.0460 (4)
H210.47480.04221.07990.055*
C220.49672 (11)−0.2115 (2)1.11034 (10)0.0481 (4)
H220.5440−0.19381.16070.058*
C230.46812 (10)−0.3798 (2)1.08362 (10)0.0449 (4)
C240.39746 (11)−0.4039 (3)1.00726 (11)0.0519 (4)
H240.3786−0.51670.98850.062*
C250.35586 (10)−0.2621 (2)0.95986 (10)0.0452 (4)
H250.3090−0.28010.90920.054*
C260.57919 (12)−0.5162 (3)1.20221 (12)0.0619 (5)
H26A0.5673−0.44771.24030.074*
H26B0.6249−0.45891.19480.074*
C270.60576 (15)−0.6989 (3)1.23413 (14)0.0752 (7)
H27A0.5606−0.75321.24240.113*
H27B0.6573−0.69411.28500.113*
H27C0.6163−0.76601.19550.113*
O1W0.17008 (10)0.6955 (2)0.74149 (10)0.0673 (4)
H1W0.1271 (11)0.701 (3)0.7493 (17)0.101*
H2W0.1963 (15)0.603 (2)0.7613 (16)0.101*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0495 (7)0.0459 (8)0.0520 (7)−0.0053 (6)0.0095 (6)0.0020 (6)
O20.0491 (7)0.0527 (8)0.0566 (8)0.0010 (6)0.0077 (6)0.0129 (6)
N10.0380 (7)0.0570 (10)0.0438 (8)0.0002 (7)0.0177 (6)−0.0018 (6)
C10.0407 (9)0.0450 (10)0.0373 (8)0.0005 (7)0.0166 (7)0.0011 (7)
C20.0360 (8)0.0368 (9)0.0333 (7)0.0022 (7)0.0123 (6)0.0023 (6)
C30.0364 (8)0.0338 (8)0.0340 (7)0.0034 (7)0.0120 (6)0.0023 (6)
C40.0394 (8)0.0370 (9)0.0350 (8)0.0070 (7)0.0114 (6)0.0013 (6)
C50.0513 (10)0.0555 (11)0.0359 (8)0.0077 (9)0.0133 (7)0.0014 (8)
C60.0595 (12)0.0641 (13)0.0357 (9)0.0115 (10)0.0053 (8)−0.0015 (8)
C70.0447 (10)0.0689 (14)0.0505 (11)0.0075 (10)−0.0003 (8)−0.0081 (10)
C80.0376 (9)0.0669 (13)0.0578 (11)0.0040 (9)0.0131 (8)−0.0063 (9)
C90.0373 (8)0.0435 (10)0.0411 (8)0.0036 (7)0.0113 (7)−0.0020 (7)
C100.0536 (11)0.0788 (14)0.0414 (9)−0.0015 (10)0.0247 (8)0.0011 (9)
C110.0375 (8)0.0431 (9)0.0300 (7)0.0014 (7)0.0131 (6)−0.0005 (6)
C120.0551 (10)0.0485 (11)0.0487 (9)0.0076 (9)0.0260 (8)0.0079 (8)
C130.0704 (13)0.0584 (12)0.0568 (11)−0.0030 (10)0.0385 (10)0.0072 (9)
C140.0504 (10)0.0673 (13)0.0540 (10)−0.0019 (9)0.0305 (9)−0.0012 (9)
C150.0483 (10)0.0583 (12)0.0533 (10)0.0091 (9)0.0249 (8)0.0023 (9)
C160.0473 (9)0.0460 (10)0.0414 (8)0.0039 (8)0.0201 (7)0.0030 (7)
C170.0365 (8)0.0434 (10)0.0315 (7)−0.0022 (7)0.0137 (6)0.0000 (6)
C180.0396 (9)0.0433 (10)0.0401 (8)−0.0018 (7)0.0117 (7)0.0023 (7)
C190.0386 (8)0.0429 (9)0.0374 (8)−0.0005 (7)0.0162 (7)−0.0025 (7)
C200.0315 (7)0.0447 (9)0.0347 (7)0.0003 (7)0.0135 (6)−0.0008 (6)
C210.0390 (9)0.0470 (10)0.0422 (9)−0.0037 (8)0.0097 (7)−0.0062 (7)
C220.0356 (8)0.0574 (12)0.0385 (8)−0.0015 (8)0.0056 (7)−0.0011 (8)
C230.0363 (8)0.0500 (11)0.0446 (9)0.0040 (8)0.0151 (7)0.0097 (8)
C240.0460 (10)0.0439 (10)0.0512 (10)−0.0048 (8)0.0093 (8)0.0008 (8)
C250.0350 (8)0.0509 (11)0.0384 (8)−0.0032 (7)0.0067 (7)−0.0016 (7)
C260.0471 (10)0.0639 (13)0.0558 (11)0.0048 (10)0.0067 (8)0.0130 (10)
C270.0647 (13)0.0706 (16)0.0712 (14)0.0141 (12)0.0139 (11)0.0229 (12)
O1W0.0615 (9)0.0736 (11)0.0734 (10)−0.0010 (8)0.0363 (8)0.0040 (8)

Geometric parameters (Å, °)

O1—C171.222 (2)C13—H130.9300
O2—C231.363 (2)C14—C151.375 (3)
O2—C261.430 (2)C14—H140.9300
N1—C11.318 (2)C15—C161.388 (2)
N1—C91.377 (2)C15—H150.9300
C1—C21.428 (2)C16—H160.9300
C1—C101.504 (2)C17—C181.460 (2)
C2—C31.381 (2)C18—C191.340 (2)
C2—C171.513 (2)C18—H180.9300
C3—C41.428 (2)C19—C201.460 (2)
C3—C111.496 (2)C19—H190.9300
C4—C91.415 (2)C20—C211.394 (2)
C4—C51.418 (2)C20—C251.398 (2)
C5—C61.365 (3)C21—C221.379 (2)
C5—H50.9300C21—H210.9300
C6—C71.401 (3)C22—C231.383 (3)
C6—H60.9300C22—H220.9300
C7—C81.365 (3)C23—C241.399 (2)
C7—H70.9300C24—C251.372 (2)
C8—C91.416 (2)C24—H240.9300
C8—H80.9300C25—H250.9300
C10—H10A0.9600C26—C271.501 (3)
C10—H10B0.9600C26—H26A0.9700
C10—H10C0.9600C26—H26B0.9700
C11—C121.388 (2)C27—H27A0.9600
C11—C161.392 (2)C27—H27B0.9600
C12—C131.386 (3)C27—H27C0.9600
C12—H120.9300O1W—H1W0.83 (2)
C13—C141.375 (3)O1W—H2W0.83 (2)
C23—O2—C26118.49 (15)C14—C15—C16120.59 (17)
C1—N1—C9118.87 (14)C14—C15—H15119.7
N1—C1—C2122.10 (14)C16—C15—H15119.7
N1—C1—C10116.33 (15)C15—C16—C11119.96 (16)
C2—C1—C10121.56 (14)C15—C16—H16120.0
C3—C2—C1120.30 (14)C11—C16—H16120.0
C3—C2—C17120.48 (14)O1—C17—C18123.42 (14)
C1—C2—C17119.18 (13)O1—C17—C2119.56 (14)
C2—C3—C4118.28 (14)C18—C17—C2117.02 (14)
C2—C3—C11120.97 (13)C19—C18—C17122.91 (16)
C4—C3—C11120.72 (13)C19—C18—H18118.5
C9—C4—C5118.18 (15)C17—C18—H18118.5
C9—C4—C3117.77 (14)C18—C19—C20126.98 (16)
C5—C4—C3124.04 (15)C18—C19—H19116.5
C6—C5—C4121.01 (18)C20—C19—H19116.5
C6—C5—H5119.5C21—C20—C25117.36 (15)
C4—C5—H5119.5C21—C20—C19120.63 (15)
C5—C6—C7120.40 (17)C25—C20—C19122.01 (14)
C5—C6—H6119.8C22—C21—C20122.15 (16)
C7—C6—H6119.8C22—C21—H21118.9
C8—C7—C6120.50 (17)C20—C21—H21118.9
C8—C7—H7119.8C21—C22—C23119.56 (15)
C6—C7—H7119.8C21—C22—H22120.2
C7—C8—C9120.31 (18)C23—C22—H22120.2
C7—C8—H8119.8O2—C23—C22125.33 (15)
C9—C8—H8119.8O2—C23—C24115.31 (16)
N1—C9—C4122.67 (14)C22—C23—C24119.35 (15)
N1—C9—C8117.72 (16)C25—C24—C23120.42 (17)
C4—C9—C8119.60 (16)C25—C24—H24119.8
C1—C10—H10A109.5C23—C24—H24119.8
C1—C10—H10B109.5C24—C25—C20121.12 (15)
H10A—C10—H10B109.5C24—C25—H25119.4
C1—C10—H10C109.5C20—C25—H25119.4
H10A—C10—H10C109.5O2—C26—C27107.53 (18)
H10B—C10—H10C109.5O2—C26—H26A110.2
C12—C11—C16119.01 (15)C27—C26—H26A110.2
C12—C11—C3120.88 (15)O2—C26—H26B110.2
C16—C11—C3120.11 (14)C27—C26—H26B110.2
C13—C12—C11120.36 (17)H26A—C26—H26B108.5
C13—C12—H12119.8C26—C27—H27A109.5
C11—C12—H12119.8C26—C27—H27B109.5
C14—C13—C12120.38 (18)H27A—C27—H27B109.5
C14—C13—H13119.8C26—C27—H27C109.5
C12—C13—H13119.8H27A—C27—H27C109.5
C13—C14—C15119.71 (17)H27B—C27—H27C109.5
C13—C14—H14120.1H1W—O1W—H2W109.0 (18)
C15—C14—H14120.1
C9—N1—C1—C20.1 (3)C16—C11—C12—C130.1 (3)
C9—N1—C1—C10179.15 (16)C3—C11—C12—C13−179.23 (16)
N1—C1—C2—C30.8 (3)C11—C12—C13—C140.0 (3)
C10—C1—C2—C3−178.20 (17)C12—C13—C14—C15−0.5 (3)
N1—C1—C2—C17178.19 (15)C13—C14—C15—C160.7 (3)
C10—C1—C2—C17−0.8 (2)C14—C15—C16—C11−0.5 (3)
C1—C2—C3—C4−0.7 (2)C12—C11—C16—C150.1 (2)
C17—C2—C3—C4−178.00 (14)C3—C11—C16—C15179.46 (15)
C1—C2—C3—C11−178.44 (15)C3—C2—C17—O174.0 (2)
C17—C2—C3—C114.2 (2)C1—C2—C17—O1−103.38 (18)
C2—C3—C4—C9−0.3 (2)C3—C2—C17—C18−106.50 (18)
C11—C3—C4—C9177.47 (15)C1—C2—C17—C1876.12 (19)
C2—C3—C4—C5−178.84 (16)O1—C17—C18—C196.8 (3)
C11—C3—C4—C5−1.1 (2)C2—C17—C18—C19−172.70 (15)
C9—C4—C5—C6−0.1 (3)C17—C18—C19—C20178.70 (15)
C3—C4—C5—C6178.44 (17)C18—C19—C20—C21−168.50 (16)
C4—C5—C6—C7−0.5 (3)C18—C19—C20—C2511.8 (3)
C5—C6—C7—C80.5 (3)C25—C20—C21—C22−2.2 (3)
C6—C7—C8—C90.1 (3)C19—C20—C21—C22178.11 (16)
C1—N1—C9—C4−1.1 (3)C20—C21—C22—C231.0 (3)
C1—N1—C9—C8178.07 (17)C26—O2—C23—C22−3.7 (3)
C5—C4—C9—N1179.87 (16)C26—O2—C23—C24176.17 (16)
C3—C4—C9—N11.3 (2)C21—C22—C23—O2−179.40 (17)
C5—C4—C9—C80.7 (2)C21—C22—C23—C240.8 (3)
C3—C4—C9—C8−177.95 (16)O2—C23—C24—C25178.97 (16)
C7—C8—C9—N1−179.94 (19)C22—C23—C24—C25−1.2 (3)
C7—C8—C9—C4−0.7 (3)C23—C24—C25—C20−0.1 (3)
C2—C3—C11—C12−118.53 (18)C21—C20—C25—C241.7 (3)
C4—C3—C11—C1263.7 (2)C19—C20—C25—C24−178.55 (16)
C2—C3—C11—C1662.1 (2)C23—O2—C26—C27−178.30 (17)
C4—C3—C11—C16−115.62 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1w—H1w···N1i0.83 (2)2.11 (2)2.934 (2)174 (2)
O1w—H2w···O10.83 (2)2.28 (2)3.082 (2)164 (3)
C26—H26b···O1ii0.972.553.507 (3)167

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5746).

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