organic compounds
(2E)-1-(2,4-Dimethylquinolin-3-yl)-3-phenylprop-2-en-1-one
aDepartment of Chemistry, BITS, Pilani–K. K. Birla Goa Campus, Goa 403 726, India, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: edward.tiekink@gmail.com
Two independent molecules comprise the 20H17NO, which differ in the orientation of the terminal phenyl ring with respect to the quinoline ring [the dihedral angles are 75.72 (11) and 84.53 (12)° for the two molecules]. The conformation about each of the ethylene bonds [1.329 (3) and 1.318 (3) Å] is E. The features a combination of C—H⋯N, C—H⋯π and π–π contacts [inter-centroid between the phenyl ring and the quinoline benzene ring is 3.6024 (19) Å], generating a three-dimensional network.
of the title compound, CRelated literature
For background details and the biological application of quinoline and quinoline et al. (2011); Prasath & Bhavana (2012); Kalanithi et al. (2012); Prasath et al. (2013). For the structures of the isomorphous chloro- and methyl-benzene derivatives, see: see: Prasath et al. (2011, 2012).
see: JoshiExperimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536813004765/hg5294sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813004765/hg5294Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813004765/hg5294Isup3.cml
A mixture of 3-acetyl-2,4-dimethylquinoline (1.0 g, 0.005 M), benzaldehyde (530 mg, 0.005 M) and KOH (0.5 g) in distilled ethanol (50 ml) was stirred for 12 h at room temperature. The resulting mixture was neutralized with dilute acetic acid. The resultant solid was filtered, dried and purified by
using a 1:1 mixture of ethyl acetate and hexane. Re-crystallization was by slow evaporation of an acetone solution of (I) which yielded colourless prisms in 80% yield; M.pt: 421–423 K.The C-bound H atoms were geometrically placed (C—H = 0.95–0.96 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). Owing to poor agreement, one reflection, i.e. (0 0 10), was removed from the final cycles of refinement.
Data collection: CrysAlis PRO (Agilent, 2011); cell
CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).C20H17NO | Z = 4 |
Mr = 287.35 | F(000) = 608 |
Triclinic, P1 | Dx = 1.225 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.1295 (9) Å | Cell parameters from 2234 reflections |
b = 11.5764 (8) Å | θ = 2.9–27.5° |
c = 13.3989 (11) Å | µ = 0.08 mm−1 |
α = 96.176 (6)° | T = 295 K |
β = 112.900 (8)° | Prism, colourless |
γ = 96.533 (6)° | 0.30 × 0.20 × 0.10 mm |
V = 1558.0 (2) Å3 |
Agilent SuperNova Dual diffractometer with an Atlas detector | 7191 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 3395 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.031 |
Detector resolution: 10.4041 pixels mm-1 | θmax = 27.6°, θmin = 2.9° |
ω scan | h = −14→12 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −15→15 |
Tmin = 0.764, Tmax = 1.000 | l = −17→17 |
14138 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.190 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0564P)2 + 0.2605P] where P = (Fo2 + 2Fc2)/3 |
7191 reflections | (Δ/σ)max = 0.001 |
401 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C20H17NO | γ = 96.533 (6)° |
Mr = 287.35 | V = 1558.0 (2) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.1295 (9) Å | Mo Kα radiation |
b = 11.5764 (8) Å | µ = 0.08 mm−1 |
c = 13.3989 (11) Å | T = 295 K |
α = 96.176 (6)° | 0.30 × 0.20 × 0.10 mm |
β = 112.900 (8)° |
Agilent SuperNova Dual diffractometer with an Atlas detector | 7191 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 3395 reflections with I > 2σ(I) |
Tmin = 0.764, Tmax = 1.000 | Rint = 0.031 |
14138 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.190 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.14 e Å−3 |
7191 reflections | Δρmin = −0.16 e Å−3 |
401 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2858 (2) | 0.45826 (19) | 0.85864 (17) | 0.0966 (7) | |
O2 | 0.5540 (2) | 1.20890 (18) | 0.82791 (16) | 0.0943 (7) | |
N1 | 0.1744 (2) | 0.77004 (18) | 0.71898 (16) | 0.0621 (5) | |
N2 | 0.5102 (2) | 0.83929 (19) | 0.69801 (17) | 0.0668 (6) | |
C1 | 0.1282 (2) | 0.7394 (2) | 0.60732 (19) | 0.0551 (6) | |
C2 | 0.0550 (3) | 0.8160 (2) | 0.5418 (2) | 0.0696 (7) | |
H2 | 0.0401 | 0.8844 | 0.5752 | 0.084* | |
C3 | 0.0063 (3) | 0.7909 (3) | 0.4306 (2) | 0.0789 (8) | |
H3 | −0.0406 | 0.8426 | 0.3884 | 0.095* | |
C4 | 0.0262 (3) | 0.6876 (3) | 0.3792 (2) | 0.0818 (9) | |
H4 | −0.0089 | 0.6703 | 0.3029 | 0.098* | |
C5 | 0.0965 (3) | 0.6123 (3) | 0.4400 (2) | 0.0710 (7) | |
H5 | 0.1095 | 0.5442 | 0.4048 | 0.085* | |
C6 | 0.1501 (2) | 0.6361 (2) | 0.55593 (18) | 0.0543 (6) | |
C7 | 0.2529 (3) | 0.4502 (2) | 0.5729 (2) | 0.0774 (8) | |
H7A | 0.2966 | 0.4060 | 0.6292 | 0.116* | |
H7B | 0.3085 | 0.4704 | 0.5355 | 0.116* | |
H7C | 0.1708 | 0.4034 | 0.5213 | 0.116* | |
C8 | 0.2260 (2) | 0.5615 (2) | 0.62422 (19) | 0.0555 (6) | |
C9 | 0.2710 (2) | 0.5937 (2) | 0.73606 (19) | 0.0567 (6) | |
C10 | 0.2425 (2) | 0.6994 (2) | 0.78072 (19) | 0.0607 (6) | |
C11 | 0.2909 (3) | 0.7357 (3) | 0.9032 (2) | 0.0895 (10) | |
H11A | 0.2705 | 0.8123 | 0.9186 | 0.134* | |
H11B | 0.3849 | 0.7385 | 0.9372 | 0.134* | |
H11C | 0.2480 | 0.6796 | 0.9318 | 0.134* | |
C12 | 0.3442 (3) | 0.5159 (2) | 0.8141 (2) | 0.0686 (7) | |
C13 | 0.4819 (3) | 0.5084 (2) | 0.8351 (2) | 0.0721 (8) | |
H13 | 0.5203 | 0.4516 | 0.8752 | 0.086* | |
C14 | 0.5556 (2) | 0.5778 (2) | 0.80014 (18) | 0.0606 (6) | |
H14 | 0.5168 | 0.6371 | 0.7644 | 0.073* | |
C15 | 0.6909 (2) | 0.5715 (2) | 0.81151 (18) | 0.0591 (6) | |
C16 | 0.7526 (3) | 0.6520 (2) | 0.7698 (2) | 0.0729 (7) | |
H16 | 0.7095 | 0.7120 | 0.7392 | 0.088* | |
C17 | 0.8772 (3) | 0.6449 (3) | 0.7728 (2) | 0.0861 (9) | |
H17 | 0.9166 | 0.6993 | 0.7437 | 0.103* | |
C18 | 0.9427 (3) | 0.5574 (3) | 0.8188 (3) | 0.0898 (10) | |
H18 | 1.0267 | 0.5525 | 0.8213 | 0.108* | |
C19 | 0.8834 (3) | 0.4780 (3) | 0.8606 (2) | 0.0908 (10) | |
H19 | 0.9275 | 0.4187 | 0.8916 | 0.109* | |
C20 | 0.7590 (3) | 0.4839 (3) | 0.8577 (2) | 0.0779 (8) | |
H20 | 0.7205 | 0.4288 | 0.8869 | 0.093* | |
C21 | 0.4459 (2) | 0.8296 (2) | 0.5867 (2) | 0.0631 (7) | |
C22 | 0.4524 (3) | 0.7285 (3) | 0.5211 (2) | 0.0821 (9) | |
H22 | 0.4984 | 0.6713 | 0.5546 | 0.099* | |
C23 | 0.3929 (3) | 0.7139 (3) | 0.4106 (3) | 0.0962 (11) | |
H23 | 0.3986 | 0.6470 | 0.3686 | 0.115* | |
C24 | 0.3232 (3) | 0.7981 (4) | 0.3590 (2) | 0.0924 (11) | |
H24 | 0.2823 | 0.7872 | 0.2827 | 0.111* | |
C25 | 0.3142 (3) | 0.8969 (3) | 0.4195 (2) | 0.0792 (9) | |
H25 | 0.2675 | 0.9527 | 0.3838 | 0.095* | |
C26 | 0.3752 (2) | 0.9158 (2) | 0.53583 (18) | 0.0595 (7) | |
C27 | 0.2962 (3) | 1.1107 (3) | 0.5540 (2) | 0.0836 (9) | |
H27A | 0.3050 | 1.1732 | 0.6109 | 0.125* | |
H27B | 0.2044 | 1.0772 | 0.5136 | 0.125* | |
H27C | 0.3312 | 1.1415 | 0.5053 | 0.125* | |
C28 | 0.3719 (2) | 1.0167 (2) | 0.60481 (19) | 0.0591 (6) | |
C29 | 0.4386 (2) | 1.0258 (2) | 0.71629 (18) | 0.0569 (6) | |
C30 | 0.5075 (3) | 0.9341 (2) | 0.76044 (19) | 0.0629 (7) | |
C31 | 0.5793 (3) | 0.9411 (3) | 0.8827 (2) | 0.0888 (9) | |
H31A | 0.6148 | 0.8701 | 0.8980 | 0.133* | |
H31B | 0.5188 | 0.9504 | 0.9169 | 0.133* | |
H31C | 0.6502 | 1.0074 | 0.9113 | 0.133* | |
C32 | 0.4519 (3) | 1.1361 (2) | 0.7940 (2) | 0.0674 (7) | |
C33 | 0.3464 (3) | 1.1558 (2) | 0.8286 (2) | 0.0712 (7) | |
H33 | 0.3522 | 1.2301 | 0.8660 | 0.085* | |
C34 | 0.2431 (3) | 1.0756 (2) | 0.81075 (18) | 0.0612 (6) | |
H34 | 0.2377 | 1.0022 | 0.7720 | 0.073* | |
C35 | 0.1350 (3) | 1.0909 (2) | 0.84622 (18) | 0.0606 (6) | |
C36 | 0.0303 (3) | 0.9987 (3) | 0.8156 (2) | 0.0750 (8) | |
H36 | 0.0306 | 0.9286 | 0.7749 | 0.090* | |
C37 | −0.0747 (3) | 1.0094 (3) | 0.8446 (3) | 0.0931 (10) | |
H37 | −0.1458 | 0.9477 | 0.8215 | 0.112* | |
C38 | −0.0734 (4) | 1.1121 (3) | 0.9081 (3) | 0.0946 (10) | |
H38 | −0.1433 | 1.1195 | 0.9286 | 0.114* | |
C39 | 0.0312 (4) | 1.2033 (3) | 0.9408 (2) | 0.0876 (9) | |
H39 | 0.0323 | 1.2722 | 0.9840 | 0.105* | |
C40 | 0.1341 (3) | 1.1932 (2) | 0.9103 (2) | 0.0736 (8) | |
H40 | 0.2042 | 1.2557 | 0.9327 | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0916 (14) | 0.0927 (16) | 0.1211 (16) | 0.0181 (12) | 0.0506 (13) | 0.0510 (13) |
O2 | 0.1028 (15) | 0.0754 (14) | 0.1009 (14) | −0.0096 (12) | 0.0510 (12) | −0.0128 (11) |
N1 | 0.0681 (13) | 0.0553 (13) | 0.0597 (12) | 0.0130 (10) | 0.0248 (10) | −0.0013 (10) |
N2 | 0.0763 (14) | 0.0619 (14) | 0.0660 (13) | 0.0166 (11) | 0.0325 (11) | 0.0076 (10) |
C1 | 0.0521 (13) | 0.0514 (14) | 0.0623 (14) | 0.0077 (11) | 0.0249 (12) | 0.0058 (11) |
C2 | 0.0700 (17) | 0.0669 (18) | 0.0777 (18) | 0.0212 (14) | 0.0328 (14) | 0.0148 (14) |
C3 | 0.0736 (18) | 0.093 (2) | 0.0800 (19) | 0.0274 (16) | 0.0336 (16) | 0.0295 (17) |
C4 | 0.0781 (19) | 0.109 (3) | 0.0582 (15) | 0.0156 (18) | 0.0277 (15) | 0.0150 (17) |
C5 | 0.0753 (18) | 0.0787 (19) | 0.0593 (15) | 0.0157 (15) | 0.0303 (14) | −0.0017 (14) |
C6 | 0.0508 (13) | 0.0525 (15) | 0.0597 (14) | 0.0049 (11) | 0.0259 (11) | 0.0005 (11) |
C7 | 0.0805 (18) | 0.0576 (17) | 0.0913 (19) | 0.0148 (14) | 0.0355 (15) | −0.0045 (14) |
C8 | 0.0510 (13) | 0.0488 (14) | 0.0660 (15) | 0.0046 (11) | 0.0272 (12) | −0.0023 (11) |
C9 | 0.0545 (14) | 0.0482 (14) | 0.0642 (14) | 0.0032 (11) | 0.0228 (12) | 0.0070 (11) |
C10 | 0.0610 (15) | 0.0572 (16) | 0.0604 (14) | 0.0056 (12) | 0.0246 (12) | 0.0001 (12) |
C11 | 0.102 (2) | 0.088 (2) | 0.0618 (16) | 0.0105 (18) | 0.0234 (16) | −0.0080 (14) |
C12 | 0.0706 (18) | 0.0555 (17) | 0.0766 (17) | 0.0064 (13) | 0.0274 (14) | 0.0124 (13) |
C13 | 0.0694 (17) | 0.0611 (17) | 0.0841 (18) | 0.0190 (14) | 0.0235 (14) | 0.0271 (14) |
C14 | 0.0642 (16) | 0.0484 (15) | 0.0606 (14) | 0.0123 (12) | 0.0167 (12) | 0.0039 (11) |
C15 | 0.0572 (15) | 0.0506 (15) | 0.0583 (14) | 0.0127 (12) | 0.0134 (12) | −0.0021 (11) |
C16 | 0.0697 (18) | 0.0649 (18) | 0.0825 (18) | 0.0135 (14) | 0.0307 (15) | 0.0043 (14) |
C17 | 0.077 (2) | 0.084 (2) | 0.101 (2) | 0.0089 (18) | 0.0449 (17) | −0.0033 (17) |
C18 | 0.0663 (19) | 0.093 (3) | 0.091 (2) | 0.0177 (19) | 0.0217 (17) | −0.0255 (18) |
C19 | 0.078 (2) | 0.084 (2) | 0.091 (2) | 0.0321 (18) | 0.0123 (18) | −0.0010 (18) |
C20 | 0.0750 (19) | 0.0688 (19) | 0.0775 (17) | 0.0197 (15) | 0.0167 (15) | 0.0082 (14) |
C21 | 0.0641 (16) | 0.0623 (17) | 0.0658 (16) | 0.0015 (13) | 0.0346 (13) | 0.0000 (13) |
C22 | 0.086 (2) | 0.073 (2) | 0.087 (2) | 0.0064 (16) | 0.0429 (17) | −0.0119 (15) |
C23 | 0.091 (2) | 0.100 (3) | 0.090 (2) | −0.003 (2) | 0.045 (2) | −0.030 (2) |
C24 | 0.086 (2) | 0.118 (3) | 0.0609 (17) | −0.009 (2) | 0.0319 (16) | −0.0170 (19) |
C25 | 0.0693 (18) | 0.100 (2) | 0.0631 (16) | −0.0008 (16) | 0.0279 (14) | 0.0053 (16) |
C26 | 0.0583 (15) | 0.0656 (17) | 0.0552 (14) | −0.0017 (13) | 0.0287 (12) | 0.0037 (12) |
C27 | 0.092 (2) | 0.081 (2) | 0.0828 (18) | 0.0267 (17) | 0.0344 (16) | 0.0262 (16) |
C28 | 0.0580 (14) | 0.0590 (16) | 0.0655 (15) | 0.0072 (12) | 0.0309 (12) | 0.0124 (12) |
C29 | 0.0636 (15) | 0.0546 (15) | 0.0568 (14) | 0.0074 (12) | 0.0303 (12) | 0.0070 (11) |
C30 | 0.0706 (16) | 0.0618 (17) | 0.0594 (14) | 0.0116 (13) | 0.0302 (13) | 0.0082 (12) |
C31 | 0.105 (2) | 0.096 (2) | 0.0651 (17) | 0.0278 (18) | 0.0304 (16) | 0.0164 (15) |
C32 | 0.0830 (19) | 0.0581 (17) | 0.0673 (15) | 0.0107 (15) | 0.0378 (15) | 0.0082 (13) |
C33 | 0.091 (2) | 0.0516 (16) | 0.0747 (16) | 0.0166 (15) | 0.0388 (15) | 0.0007 (12) |
C34 | 0.0803 (17) | 0.0479 (14) | 0.0583 (14) | 0.0184 (13) | 0.0299 (13) | 0.0065 (11) |
C35 | 0.0791 (17) | 0.0566 (16) | 0.0535 (13) | 0.0240 (14) | 0.0305 (13) | 0.0133 (11) |
C36 | 0.094 (2) | 0.0649 (18) | 0.0807 (18) | 0.0198 (16) | 0.0505 (16) | 0.0073 (14) |
C37 | 0.099 (2) | 0.088 (2) | 0.112 (2) | 0.0121 (19) | 0.066 (2) | 0.0089 (19) |
C38 | 0.114 (3) | 0.102 (3) | 0.103 (2) | 0.046 (2) | 0.071 (2) | 0.024 (2) |
C39 | 0.123 (3) | 0.076 (2) | 0.0821 (19) | 0.047 (2) | 0.053 (2) | 0.0120 (16) |
C40 | 0.090 (2) | 0.0636 (18) | 0.0726 (17) | 0.0267 (15) | 0.0361 (16) | 0.0086 (13) |
O1—C12 | 1.229 (3) | C19—C20 | 1.379 (4) |
O2—C32 | 1.228 (3) | C19—H19 | 0.9300 |
N1—C10 | 1.315 (3) | C20—H20 | 0.9300 |
N1—C1 | 1.369 (3) | C21—C26 | 1.409 (4) |
N2—C30 | 1.317 (3) | C21—C22 | 1.413 (4) |
N2—C21 | 1.365 (3) | C22—C23 | 1.349 (4) |
C1—C6 | 1.408 (3) | C22—H22 | 0.9300 |
C1—C2 | 1.413 (3) | C23—C24 | 1.390 (5) |
C2—C3 | 1.356 (4) | C23—H23 | 0.9300 |
C2—H2 | 0.9300 | C24—C25 | 1.366 (4) |
C3—C4 | 1.398 (4) | C24—H24 | 0.9300 |
C3—H3 | 0.9300 | C25—C26 | 1.417 (3) |
C4—C5 | 1.360 (4) | C25—H25 | 0.9300 |
C4—H4 | 0.9300 | C26—C28 | 1.423 (3) |
C5—C6 | 1.412 (3) | C27—C28 | 1.510 (4) |
C5—H5 | 0.9300 | C27—H27A | 0.9600 |
C6—C8 | 1.426 (3) | C27—H27B | 0.9600 |
C7—C8 | 1.510 (3) | C27—H27C | 0.9600 |
C7—H7A | 0.9600 | C28—C29 | 1.371 (3) |
C7—H7B | 0.9600 | C29—C30 | 1.426 (4) |
C7—H7C | 0.9600 | C29—C32 | 1.512 (3) |
C8—C9 | 1.374 (3) | C30—C31 | 1.506 (3) |
C9—C10 | 1.426 (3) | C31—H31A | 0.9600 |
C9—C12 | 1.508 (3) | C31—H31B | 0.9600 |
C10—C11 | 1.507 (3) | C31—H31C | 0.9600 |
C11—H11A | 0.9600 | C32—C33 | 1.451 (4) |
C11—H11B | 0.9600 | C33—C34 | 1.318 (3) |
C11—H11C | 0.9600 | C33—H33 | 0.9300 |
C12—C13 | 1.461 (4) | C34—C35 | 1.476 (4) |
C13—C14 | 1.329 (3) | C34—H34 | 0.9300 |
C13—H13 | 0.9300 | C35—C36 | 1.384 (4) |
C14—C15 | 1.464 (3) | C35—C40 | 1.390 (3) |
C14—H14 | 0.9300 | C36—C37 | 1.380 (4) |
C15—C16 | 1.385 (3) | C36—H36 | 0.9300 |
C15—C20 | 1.390 (3) | C37—C38 | 1.381 (4) |
C16—C17 | 1.384 (4) | C37—H37 | 0.9300 |
C16—H16 | 0.9300 | C38—C39 | 1.373 (4) |
C17—C18 | 1.374 (4) | C38—H38 | 0.9300 |
C17—H17 | 0.9300 | C39—C40 | 1.369 (4) |
C18—C19 | 1.362 (4) | C39—H39 | 0.9300 |
C18—H18 | 0.9300 | C40—H40 | 0.9300 |
C10—N1—C1 | 118.1 (2) | C15—C20—H20 | 119.8 |
C30—N2—C21 | 118.5 (2) | N2—C21—C26 | 122.9 (2) |
N1—C1—C6 | 123.2 (2) | N2—C21—C22 | 117.6 (3) |
N1—C1—C2 | 117.6 (2) | C26—C21—C22 | 119.5 (2) |
C6—C1—C2 | 119.2 (2) | C23—C22—C21 | 120.9 (3) |
C3—C2—C1 | 120.6 (3) | C23—C22—H22 | 119.5 |
C3—C2—H2 | 119.7 | C21—C22—H22 | 119.5 |
C1—C2—H2 | 119.7 | C22—C23—C24 | 120.4 (3) |
C2—C3—C4 | 120.3 (3) | C22—C23—H23 | 119.8 |
C2—C3—H3 | 119.8 | C24—C23—H23 | 119.8 |
C4—C3—H3 | 119.8 | C25—C24—C23 | 120.5 (3) |
C5—C4—C3 | 120.4 (3) | C25—C24—H24 | 119.8 |
C5—C4—H4 | 119.8 | C23—C24—H24 | 119.8 |
C3—C4—H4 | 119.8 | C24—C25—C26 | 121.0 (3) |
C4—C5—C6 | 120.9 (3) | C24—C25—H25 | 119.5 |
C4—C5—H5 | 119.6 | C26—C25—H25 | 119.5 |
C6—C5—H5 | 119.6 | C21—C26—C25 | 117.8 (3) |
C1—C6—C5 | 118.5 (2) | C21—C26—C28 | 117.7 (2) |
C1—C6—C8 | 118.0 (2) | C25—C26—C28 | 124.5 (3) |
C5—C6—C8 | 123.6 (2) | C28—C27—H27A | 109.5 |
C8—C7—H7A | 109.5 | C28—C27—H27B | 109.5 |
C8—C7—H7B | 109.5 | H27A—C27—H27B | 109.5 |
H7A—C7—H7B | 109.5 | C28—C27—H27C | 109.5 |
C8—C7—H7C | 109.5 | H27A—C27—H27C | 109.5 |
H7A—C7—H7C | 109.5 | H27B—C27—H27C | 109.5 |
H7B—C7—H7C | 109.5 | C29—C28—C26 | 118.7 (2) |
C9—C8—C6 | 117.9 (2) | C29—C28—C27 | 121.8 (2) |
C9—C8—C7 | 122.2 (2) | C26—C28—C27 | 119.6 (2) |
C6—C8—C7 | 119.9 (2) | C28—C29—C30 | 119.7 (2) |
C8—C9—C10 | 120.1 (2) | C28—C29—C32 | 121.7 (2) |
C8—C9—C12 | 121.5 (2) | C30—C29—C32 | 118.4 (2) |
C10—C9—C12 | 118.3 (2) | N2—C30—C29 | 122.5 (2) |
N1—C10—C9 | 122.7 (2) | N2—C30—C31 | 116.8 (2) |
N1—C10—C11 | 116.5 (2) | C29—C30—C31 | 120.6 (2) |
C9—C10—C11 | 120.8 (2) | C30—C31—H31A | 109.5 |
C10—C11—H11A | 109.5 | C30—C31—H31B | 109.5 |
C10—C11—H11B | 109.5 | H31A—C31—H31B | 109.5 |
H11A—C11—H11B | 109.5 | C30—C31—H31C | 109.5 |
C10—C11—H11C | 109.5 | H31A—C31—H31C | 109.5 |
H11A—C11—H11C | 109.5 | H31B—C31—H31C | 109.5 |
H11B—C11—H11C | 109.5 | O2—C32—C33 | 120.3 (3) |
O1—C12—C13 | 120.8 (3) | O2—C32—C29 | 118.8 (3) |
O1—C12—C9 | 119.0 (3) | C33—C32—C29 | 120.9 (2) |
C13—C12—C9 | 120.2 (2) | C34—C33—C32 | 124.5 (3) |
C14—C13—C12 | 124.0 (2) | C34—C33—H33 | 117.7 |
C14—C13—H13 | 118.0 | C32—C33—H33 | 117.7 |
C12—C13—H13 | 118.0 | C33—C34—C35 | 126.4 (2) |
C13—C14—C15 | 127.4 (2) | C33—C34—H34 | 116.8 |
C13—C14—H14 | 116.3 | C35—C34—H34 | 116.8 |
C15—C14—H14 | 116.3 | C36—C35—C40 | 118.2 (3) |
C16—C15—C20 | 117.7 (3) | C36—C35—C34 | 118.7 (2) |
C16—C15—C14 | 119.4 (2) | C40—C35—C34 | 123.0 (3) |
C20—C15—C14 | 122.8 (3) | C37—C36—C35 | 121.0 (3) |
C17—C16—C15 | 121.3 (3) | C37—C36—H36 | 119.5 |
C17—C16—H16 | 119.4 | C35—C36—H36 | 119.5 |
C15—C16—H16 | 119.4 | C36—C37—C38 | 119.6 (3) |
C18—C17—C16 | 120.0 (3) | C36—C37—H37 | 120.2 |
C18—C17—H17 | 120.0 | C38—C37—H37 | 120.2 |
C16—C17—H17 | 120.0 | C39—C38—C37 | 119.9 (3) |
C19—C18—C17 | 119.3 (3) | C39—C38—H38 | 120.1 |
C19—C18—H18 | 120.4 | C37—C38—H38 | 120.1 |
C17—C18—H18 | 120.4 | C40—C39—C38 | 120.4 (3) |
C18—C19—C20 | 121.2 (3) | C40—C39—H39 | 119.8 |
C18—C19—H19 | 119.4 | C38—C39—H39 | 119.8 |
C20—C19—H19 | 119.4 | C39—C40—C35 | 120.8 (3) |
C19—C20—C15 | 120.5 (3) | C39—C40—H40 | 119.6 |
C19—C20—H20 | 119.8 | C35—C40—H40 | 119.6 |
C10—N1—C1—C6 | 0.1 (3) | C30—N2—C21—C26 | −1.0 (4) |
C10—N1—C1—C2 | 180.0 (2) | C30—N2—C21—C22 | 178.6 (2) |
N1—C1—C2—C3 | −179.9 (2) | N2—C21—C22—C23 | −179.1 (2) |
C6—C1—C2—C3 | −0.1 (4) | C26—C21—C22—C23 | 0.6 (4) |
C1—C2—C3—C4 | 1.0 (4) | C21—C22—C23—C24 | −0.3 (5) |
C2—C3—C4—C5 | −1.2 (4) | C22—C23—C24—C25 | 0.1 (5) |
C3—C4—C5—C6 | 0.4 (4) | C23—C24—C25—C26 | −0.2 (4) |
N1—C1—C6—C5 | 179.2 (2) | N2—C21—C26—C25 | 179.0 (2) |
C2—C1—C6—C5 | −0.6 (3) | C22—C21—C26—C25 | −0.6 (4) |
N1—C1—C6—C8 | −1.1 (3) | N2—C21—C26—C28 | 0.1 (4) |
C2—C1—C6—C8 | 179.1 (2) | C22—C21—C26—C28 | −179.5 (2) |
C4—C5—C6—C1 | 0.5 (4) | C24—C25—C26—C21 | 0.5 (4) |
C4—C5—C6—C8 | −179.2 (2) | C24—C25—C26—C28 | 179.2 (2) |
C1—C6—C8—C9 | 1.2 (3) | C21—C26—C28—C29 | 0.9 (3) |
C5—C6—C8—C9 | −179.1 (2) | C25—C26—C28—C29 | −177.9 (2) |
C1—C6—C8—C7 | −179.5 (2) | C21—C26—C28—C27 | −179.4 (2) |
C5—C6—C8—C7 | 0.1 (4) | C25—C26—C28—C27 | 1.8 (4) |
C6—C8—C9—C10 | −0.5 (3) | C26—C28—C29—C30 | −1.0 (3) |
C7—C8—C9—C10 | −179.7 (2) | C27—C28—C29—C30 | 179.3 (2) |
C6—C8—C9—C12 | 175.9 (2) | C26—C28—C29—C32 | 173.4 (2) |
C7—C8—C9—C12 | −3.3 (4) | C27—C28—C29—C32 | −6.3 (4) |
C1—N1—C10—C9 | 0.7 (4) | C21—N2—C30—C29 | 0.9 (4) |
C1—N1—C10—C11 | −179.6 (2) | C21—N2—C30—C31 | 179.8 (2) |
C8—C9—C10—N1 | −0.5 (4) | C28—C29—C30—N2 | 0.1 (4) |
C12—C9—C10—N1 | −177.0 (2) | C32—C29—C30—N2 | −174.5 (2) |
C8—C9—C10—C11 | 179.8 (2) | C28—C29—C30—C31 | −178.8 (2) |
C12—C9—C10—C11 | 3.4 (4) | C32—C29—C30—C31 | 6.6 (4) |
C8—C9—C12—O1 | −103.9 (3) | C28—C29—C32—O2 | −97.8 (3) |
C10—C9—C12—O1 | 72.5 (3) | C30—C29—C32—O2 | 76.7 (3) |
C8—C9—C12—C13 | 75.3 (3) | C28—C29—C32—C33 | 82.5 (3) |
C10—C9—C12—C13 | −108.3 (3) | C30—C29—C32—C33 | −103.1 (3) |
O1—C12—C13—C14 | −171.9 (3) | O2—C32—C33—C34 | −169.0 (3) |
C9—C12—C13—C14 | 8.9 (4) | C29—C32—C33—C34 | 10.8 (4) |
C12—C13—C14—C15 | −175.9 (2) | C32—C33—C34—C35 | 178.7 (2) |
C13—C14—C15—C16 | −179.9 (2) | C33—C34—C35—C36 | 176.9 (2) |
C13—C14—C15—C20 | 3.5 (4) | C33—C34—C35—C40 | −3.9 (4) |
C20—C15—C16—C17 | 0.7 (4) | C40—C35—C36—C37 | 2.2 (4) |
C14—C15—C16—C17 | −176.0 (2) | C34—C35—C36—C37 | −178.6 (2) |
C15—C16—C17—C18 | −0.6 (4) | C35—C36—C37—C38 | −2.1 (5) |
C16—C17—C18—C19 | 0.3 (4) | C36—C37—C38—C39 | 0.7 (5) |
C17—C18—C19—C20 | −0.1 (4) | C37—C38—C39—C40 | 0.4 (5) |
C18—C19—C20—C15 | 0.2 (4) | C38—C39—C40—C35 | −0.3 (4) |
C16—C15—C20—C19 | −0.5 (4) | C36—C35—C40—C39 | −1.0 (4) |
C14—C15—C20—C19 | 176.2 (2) | C34—C35—C40—C39 | 179.8 (2) |
Cg1 and Cg2 are the centroids of the C1–C6 and C15–C20 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···N2 | 0.93 | 2.59 | 3.463 (3) | 156 |
C7—H7C···Cg1i | 0.96 | 2.86 | 3.662 (3) | 142 |
C39—H39···Cg2ii | 0.93 | 2.88 | 3.679 (3) | 145 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C20H17NO |
Mr | 287.35 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 11.1295 (9), 11.5764 (8), 13.3989 (11) |
α, β, γ (°) | 96.176 (6), 112.900 (8), 96.533 (6) |
V (Å3) | 1558.0 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Agilent SuperNova Dual diffractometer with an Atlas detector |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2011) |
Tmin, Tmax | 0.764, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14138, 7191, 3395 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.190, 1.05 |
No. of reflections | 7191 |
No. of parameters | 401 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.16 |
Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).
Cg1 and Cg2 are the centroids of the C1–C6 and C15–C20 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···N2 | 0.93 | 2.59 | 3.463 (3) | 156 |
C7—H7C···Cg1i | 0.96 | 2.86 | 3.662 (3) | 142 |
C39—H39···Cg2ii | 0.93 | 2.88 | 3.679 (3) | 145 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+2, −z+2. |
Footnotes
‡Additional correspondence author, e-mail: juliebhavana@gmail.com.
Acknowledgements
PB and RP gratefully acknowledge the Council of Scientific and Industrial Research (CSIR), India, for research grant 02 (0076)/12/EMR-II and Senior Research Fellowship (09/919/(0014)/2012 EMR-I), respectively. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Quinoline and their corresponding heterocyclic analogues are valuable intermediates in organic synthesis and exhibit a multitude of biological activities. (Prasath & Bhavana, 2012; Joshi et al., 2011). Quinoline chalcone analogues have also gained much attention due to their bioactivity such as anti-plasmodial, anti-microbial, anti-malarial and anti-cancer activities (Prasath et al., 2013; Kalanithi et al., 2012). In was in this connection, that the title compound, (I), was investigated.
Two crystallographically independent molecules comprise the asymmetric unit of (I), Fig. 1. As clearly indicated in Fig. 2, an overlay diagram of the molecules, the major difference between them is manifested in the dihedral angles formed by the ten atoms of the quinolinyl ring (r.m.s. deviations = 0.010 and 0.013 Å) and the terminal phenyl ring, i.e. 75.72 (11)° for the N1-containing molecule and 84.53 (12)° for the N2-containing molecule. The overall conformation of each molecule is therefore of the letter L. The configuration around each ethylene bond [C13═C14 = 1.329 (3) Å and C33═C34 = 1.318 (3) Å] is E. The overall molecular conformation found for the molecules comprising (I) match those of the chloro- (Prasath et al., 2011) and methyl-benzene (Prasath et al., 2012) analogues; the three structures are in fact isomorphous.
The three-dimensional architecture is stabilized by a combination of ethylene-C—H···N2 interactions [between the independent molecules] and C—H···π interactions between methyl-H and a C6 ring of the N1-quinolinyl residue, and between phenyl-H and the phenyl (C15–C20) ring, Table 1, along with π···π contacts between the independent molecules [inter-centroid distance = 3.6024 (19) Å, angle of inclination = 2.43 (15)°], i.e. between the C6 ring of the N1-quinolinyl residue and the phenyl (C35–C40) ring of the N2-containing molecule, Fig. 3.