(2E)-3-(6-Chloro-2-meth­oxy­quinolin-3-yl)-1-(2,4-di­methyl­quinolin-3-yl)prop-2-en-1-one

Prasath, R.; Sarveswari, S.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536813019399

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1274

doi:10.1107/S1600536813019399

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(2E)-3-(6-Chloro-2-methoxyquinolin-3-yl)-1-(2,4-dimethylquinolin-3-yl)prop-2-en-1-one

R. Prasath,^a ‡ S. Sarveswari,^b Seik Weng Ng ^c,^d and Edward R. T. Tiekink ^c ^*

^aDepartment of Chemistry, BITS, Pilani – K. K. Birla Goa Campus, Goa 403 726, India, ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 12 July 2013; accepted 13 July 2013; online 20 July 2013)

The molecule of the title compound, C₂₄H₁₉ClN₂O₂, is bent, with the dihedral angle between the terminal quinoline ring systems being 63.30 (5)°. The quinolinyl residues are connected by an almost planar prop-2-en-1-one bridge (r.m.s. deviation = 0.022 Å), with the dihedral angles between this plane and the appended quinolinyl residues being 75.86 (7) and 38.54 (7)°. The C atom of the methoxy group is close to coplanar with its attached ring [deviation = 0.116 (2) Å]. In the crystal, a three-dimensional architecture is constructed by methyl–carbonyl C—H⋯O interactions and π–π interactions between centrosymmetrically related quinolinyl residues [centroid-to-centroid separations 3.5341 (10) and 3.8719 (9) Å].

Related literature

For background to the biological activities and photophysical properties of quinolines, and their utility as intermediates in organic synthesis, see: Prasath & Bhavana (2012 ); Joshi et al. (2011 ). For background to the bio-activities of quinolinyl chalcones, see: Prasath et al. (2013a ). For a related structure, see: Prasath et al. (2013b ).

Experimental

Crystal data

C₂₄H₁₉ClN₂O₂
M_r = 402.86
Monoclinic, P 2₁ /n
a = 13.1605 (3) Å
b = 10.4876 (2) Å
c = 14.8786 (3) Å
β = 106.354 (2)°
V = 1970.49 (7) Å³
Z = 4
Cu Kα radiation
μ = 1.90 mm⁻¹
T = 100 K
0.35 × 0.30 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ) T_min = 0.711, T_max = 1.000
8189 measured reflections
4053 independent reflections
3580 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.127
S = 1.07
4053 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O1ⁱ	0.98	2.52	3.221 (2)	129
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: 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 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813019399/hb7107sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813019399/hb7107Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813019399/hb7107Isup3.cml

checkCIF report

Comment top

Quinoline derivatives are an important class of natural and synthetic products, which possess a number of interesting biological activities, are valuable intermediates in organic synthesis, and exhibit a multitude of photo-physical properties (Prasath & Bhavana, 2012; Joshi et al., 2011). Also, quinolinyl chalcones have gained much attention due to their bio-activity, such as anti-bacterial, anti-fungal, anti-malarial and anti-cancer activities (Prasath et al., 2013a). It was in this connection that the title compound, (I), was investigated.

The molecular structure of (I), Fig. 1, comprises two quinolinyl rings connected by the ends of a prop-2-en-1-one bridge. The dihedral angle between the quinolinyl rings is 63.30 (5)°. The methoxy group is coplanar with the quinolinyl ring to which it is attached, as seen in the value of the C24—O2—C16—N2 torsion angle of 3.1 (2)°. The conformation about the ethylene bond [C13═C14 = 1.335 (2) Å] is E. The central C₅O plane comprising the O1, C8 and C12–C15 atoms, is almost planar, with an r.m.s. deviation of 0.022 Å. The N1- and N2-containing quinolinyl rings form dihedral angles of 75.86 (7) and 38.54 (7)°, respectively, with the central plane.

In the most closely related structure, (II), namely (2E)-3-(2-chloro-8-methylquinolin-3-yl)-1-(5,7-dimethylquinolin-6-yl)prop-2-en-1-one (Prasath et al., 2013b), the dihedral angle between the quinolinyl residues is 83.72 (4)°, indicating a more open configuration than that in (I). Also, when the structures are viewed normal to the ethylene bond, the pyridyl-N atoms in (I) can be described as syn, whereas they are closer to anti in (II).

In the crystal, supramolecular helical chains are formed by methyl-C—H···O(carbonyl) interactions, Table 1. These are connected into a three-dimensional architecture by π–π interactions between the rings of centrosymmetrically related N1-quinolinyl residues [3.5341 (10) Å; angle of inclination = 2.48 (9)° for symmetry operation 1 - x, 1 - y, -z] and between the rings of centrosymmetrically related N2-quinolinyl residues [3.8719 (9) Å; angle of inclination = 2.52 (8)° for symmetry operation 1 - x, 2 - y, -z], Fig. 2.

Related literature top

For background to the biological activities and photophysical properties of quinolines, and their utility as intermediates in organic synthesis, see: Prasath & Bhavana (2012); Joshi et al. (2011). For background to the bio-activities of quinolinyl chalcones, see: Prasath et al. (2013a). For a related structure, see: Prasath et al. (2013b).

Experimental top

A mixture of 2,4-dimethyl-3-acetylquinoline (200 mg, 0.001 M) and 2,6-dichloroquinoline-3-carbaldehyde (230 mg, 0.001 M) in methanol (20 ml) containing 0.2 g of potassium hydroxide was stirred at room temperature for 12 h. At the end of the period, the reaction mixture was neutralized with dilute acetic acid and the resultant solid was filtered, dried and purified by column chromatography using ethyl acetate–hexane (2:1) mixture to afford (I). Re-crystallization was by slow evaporation of an acetone solution of (I), which yielded pale-yellow blocks in 61% yield; M.pt: 423–425 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); 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) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 50% probability level.
	Fig. 2. A view, in projection down the a axis, of the unit-cell contents of (I). The C—H···O and π–π interactions are shown as orange and purple blue dashed lines, respectively.

(2E)-3-(6-Chloro-2-methoxyquinolin-3-yl)-1-(2,4-dimethylquinolin-3-yl)prop-2-en-1-one top

Crystal data top

C₂₄H₁₉ClN₂O₂	F(000) = 840
M_r = 402.86	D_x = 1.358 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 4094 reflections
a = 13.1605 (3) Å	θ = 3.1–76.4°
b = 10.4876 (2) Å	µ = 1.90 mm⁻¹
c = 14.8786 (3) Å	T = 100 K
β = 106.354 (2)°	Block, pale-yellow
V = 1970.49 (7) Å³	0.35 × 0.30 × 0.25 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	4053 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3580 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.019
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.6°, θ_min = 4.0°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −12→13
T_min = 0.711, T_max = 1.000	l = −18→18
8189 measured reflections

Refinement top

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0675P)² + 0.8422P] where P = (F_o² + 2F_c²)/3
4053 reflections	(Δ/σ)_max = 0.001
264 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₂₄H₁₉ClN₂O₂	V = 1970.49 (7) Å³
M_r = 402.86	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 13.1605 (3) Å	µ = 1.90 mm⁻¹
b = 10.4876 (2) Å	T = 100 K
c = 14.8786 (3) Å	0.35 × 0.30 × 0.25 mm
β = 106.354 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	4053 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	3580 reflections with I > 2σ(I)
T_min = 0.711, T_max = 1.000	R_int = 0.019
8189 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.07	Δρ_max = 0.61 e Å⁻³
4053 reflections	Δρ_min = −0.49 e Å⁻³
264 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
Cl1	0.69700 (4)	1.15984 (5)	0.82007 (3)	0.03903 (15)
O1	0.74055 (11)	0.52819 (14)	0.32665 (9)	0.0379 (3)
O2	0.34467 (11)	0.69372 (12)	0.42578 (8)	0.0324 (3)
N1	0.40195 (12)	0.49117 (14)	0.14020 (10)	0.0271 (3)
N2	0.39020 (11)	0.82891 (14)	0.55617 (10)	0.0249 (3)
C1	0.40917 (13)	0.56639 (17)	0.06701 (12)	0.0252 (3)
C2	0.32879 (14)	0.55356 (17)	−0.01880 (12)	0.0284 (4)
H2	0.2728	0.4945	−0.0237	0.034*
C3	0.33138 (15)	0.62559 (19)	−0.09439 (12)	0.0319 (4)
H3	0.2776	0.6155	−0.1519	0.038*
C4	0.41310 (15)	0.7150 (2)	−0.08803 (13)	0.0338 (4)
H4	0.4130	0.7664	−0.1406	0.041*
C5	0.49274 (15)	0.72798 (18)	−0.00624 (13)	0.0302 (4)
H5	0.5479	0.7878	−0.0026	0.036*
C6	0.49323 (13)	0.65264 (16)	0.07298 (12)	0.0247 (3)
C7	0.57710 (13)	0.65747 (16)	0.15858 (12)	0.0256 (4)
C8	0.56830 (13)	0.58072 (16)	0.23097 (11)	0.0250 (3)
C9	0.47856 (14)	0.49875 (17)	0.21924 (12)	0.0271 (4)
C10	0.67212 (14)	0.74029 (19)	0.16571 (13)	0.0323 (4)
H10A	0.7189	0.7374	0.2299	0.048*
H10B	0.6491	0.8283	0.1496	0.048*
H10C	0.7104	0.7092	0.1223	0.048*
C11	0.46915 (18)	0.4122 (2)	0.29718 (14)	0.0394 (5)
H11A	0.4195	0.3430	0.2712	0.059*
H11B	0.4431	0.4610	0.3423	0.059*
H11C	0.5388	0.3762	0.3288	0.059*
C12	0.65569 (14)	0.57938 (17)	0.32225 (12)	0.0269 (4)
C13	0.63785 (14)	0.64480 (17)	0.40412 (12)	0.0270 (4)
H13	0.6935	0.6466	0.4609	0.032*
C14	0.54619 (13)	0.70161 (16)	0.40128 (11)	0.0242 (3)
H14	0.4909	0.6960	0.3444	0.029*
C15	0.52396 (13)	0.77189 (16)	0.47882 (11)	0.0231 (3)
C16	0.41937 (13)	0.76998 (16)	0.49044 (11)	0.0247 (3)
C17	0.46563 (13)	0.90084 (16)	0.61874 (11)	0.0237 (3)
C18	0.43667 (14)	0.96369 (17)	0.69184 (12)	0.0278 (4)
H18	0.3674	0.9532	0.6983	0.033*
C19	0.50854 (15)	1.04000 (17)	0.75364 (12)	0.0293 (4)
H19	0.4891	1.0819	0.8029	0.035*
C20	0.61116 (14)	1.05587 (17)	0.74370 (12)	0.0282 (4)
C21	0.64352 (14)	0.99357 (16)	0.67556 (12)	0.0259 (3)
H21	0.7135	1.0042	0.6707	0.031*
C22	0.57067 (13)	0.91316 (15)	0.61268 (11)	0.0226 (3)
C23	0.59830 (13)	0.84460 (15)	0.54060 (11)	0.0235 (3)
H23	0.6684	0.8492	0.5352	0.028*
C24	0.24358 (17)	0.6907 (2)	0.43289 (16)	0.0437 (5)
H24A	0.2003	0.6347	0.3843	0.066*
H24B	0.2138	0.7770	0.4247	0.066*
H24C	0.2440	0.6583	0.4947	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0375 (3)	0.0398 (3)	0.0358 (3)	−0.00176 (19)	0.00367 (19)	−0.01474 (18)
O1	0.0302 (7)	0.0444 (8)	0.0365 (7)	0.0107 (6)	0.0051 (5)	−0.0085 (6)
O2	0.0458 (8)	0.0284 (6)	0.0201 (6)	0.0077 (6)	0.0046 (5)	−0.0081 (5)
N1	0.0278 (7)	0.0249 (7)	0.0285 (7)	−0.0001 (6)	0.0077 (6)	−0.0012 (6)
N2	0.0247 (7)	0.0242 (7)	0.0260 (7)	0.0009 (5)	0.0076 (6)	0.0004 (5)
C1	0.0258 (8)	0.0247 (8)	0.0267 (8)	0.0034 (6)	0.0101 (6)	−0.0030 (6)
C2	0.0261 (8)	0.0287 (9)	0.0300 (8)	0.0027 (7)	0.0075 (7)	−0.0039 (7)
C3	0.0277 (9)	0.0392 (10)	0.0263 (8)	0.0069 (8)	0.0037 (7)	−0.0012 (7)
C4	0.0333 (9)	0.0398 (10)	0.0297 (9)	0.0066 (8)	0.0110 (7)	0.0076 (8)
C5	0.0288 (9)	0.0330 (9)	0.0315 (9)	0.0008 (7)	0.0127 (7)	0.0033 (7)
C6	0.0262 (8)	0.0242 (8)	0.0256 (8)	0.0043 (6)	0.0102 (7)	−0.0016 (6)
C7	0.0258 (8)	0.0258 (8)	0.0269 (8)	0.0028 (7)	0.0104 (7)	−0.0041 (6)
C8	0.0268 (8)	0.0244 (8)	0.0239 (8)	0.0045 (7)	0.0070 (6)	−0.0046 (6)
C9	0.0297 (9)	0.0240 (8)	0.0272 (8)	0.0016 (7)	0.0074 (7)	−0.0012 (6)
C10	0.0298 (9)	0.0374 (10)	0.0311 (9)	−0.0024 (8)	0.0109 (7)	−0.0028 (7)
C11	0.0462 (11)	0.0334 (10)	0.0354 (10)	−0.0083 (9)	0.0065 (8)	0.0062 (8)
C12	0.0267 (8)	0.0255 (8)	0.0277 (8)	0.0029 (7)	0.0064 (7)	−0.0019 (7)
C13	0.0291 (8)	0.0275 (9)	0.0222 (8)	0.0022 (7)	0.0036 (6)	−0.0009 (6)
C14	0.0275 (8)	0.0240 (8)	0.0209 (7)	0.0005 (6)	0.0066 (6)	0.0008 (6)
C15	0.0263 (8)	0.0221 (8)	0.0206 (7)	0.0032 (6)	0.0061 (6)	0.0033 (6)
C16	0.0252 (8)	0.0226 (8)	0.0248 (8)	0.0004 (6)	0.0048 (6)	0.0014 (6)
C17	0.0253 (8)	0.0222 (8)	0.0235 (7)	0.0033 (6)	0.0067 (6)	0.0035 (6)
C18	0.0283 (8)	0.0278 (8)	0.0288 (8)	0.0044 (7)	0.0107 (7)	0.0007 (7)
C19	0.0332 (9)	0.0292 (9)	0.0263 (8)	0.0061 (7)	0.0097 (7)	−0.0025 (7)
C20	0.0315 (9)	0.0253 (8)	0.0248 (8)	0.0030 (7)	0.0030 (7)	−0.0017 (6)
C21	0.0254 (8)	0.0250 (8)	0.0261 (8)	0.0024 (7)	0.0054 (6)	0.0015 (6)
C22	0.0252 (8)	0.0207 (7)	0.0214 (7)	0.0038 (6)	0.0055 (6)	0.0035 (6)
C23	0.0247 (8)	0.0226 (8)	0.0236 (8)	0.0024 (6)	0.0074 (6)	0.0026 (6)
C24	0.0387 (11)	0.0444 (12)	0.0467 (12)	−0.0044 (9)	0.0101 (9)	−0.0109 (10)

Geometric parameters (Å, º) top

Cl1—C20	1.7417 (18)	C10—H10C	0.9800
O1—C12	1.224 (2)	C11—H11A	0.9800
O2—C24	1.364 (3)	C11—H11B	0.9800
O2—C16	1.414 (2)	C11—H11C	0.9800
N1—C9	1.318 (2)	C12—C13	1.473 (2)
N1—C1	1.369 (2)	C13—C14	1.335 (2)
N2—C16	1.303 (2)	C13—H13	0.9500
N2—C17	1.379 (2)	C14—C15	1.466 (2)
C1—C6	1.412 (2)	C14—H14	0.9500
C1—C2	1.416 (2)	C15—C23	1.370 (2)
C2—C3	1.363 (3)	C15—C16	1.435 (2)
C2—H2	0.9500	C17—C18	1.413 (2)
C3—C4	1.409 (3)	C17—C22	1.416 (2)
C3—H3	0.9500	C18—C19	1.375 (3)
C4—C5	1.371 (3)	C18—H18	0.9500
C4—H4	0.9500	C19—C20	1.409 (3)
C5—C6	1.417 (2)	C19—H19	0.9500
C5—H5	0.9500	C20—C21	1.371 (2)
C6—C7	1.432 (2)	C21—C22	1.414 (2)
C7—C8	1.375 (2)	C21—H21	0.9500
C7—C10	1.502 (2)	C22—C23	1.421 (2)
C8—C9	1.431 (2)	C23—H23	0.9500
C8—C12	1.513 (2)	C24—H24A	0.9800
C9—C11	1.505 (2)	C24—H24B	0.9800
C10—H10A	0.9800	C24—H24C	0.9800
C10—H10B	0.9800

C24—O2—C16	117.82 (14)	O1—C12—C13	121.03 (16)
C9—N1—C1	117.89 (15)	O1—C12—C8	120.25 (15)
C16—N2—C17	117.27 (15)	C13—C12—C8	118.69 (14)
N1—C1—C6	123.19 (15)	C14—C13—C12	122.30 (16)
N1—C1—C2	117.43 (16)	C14—C13—H13	118.8
C6—C1—C2	119.37 (16)	C12—C13—H13	118.8
C3—C2—C1	120.35 (17)	C13—C14—C15	125.30 (15)
C3—C2—H2	119.8	C13—C14—H14	117.3
C1—C2—H2	119.8	C15—C14—H14	117.3
C2—C3—C4	120.59 (17)	C23—C15—C16	117.06 (15)
C2—C3—H3	119.7	C23—C15—C14	123.01 (15)
C4—C3—H3	119.7	C16—C15—C14	119.90 (15)
C5—C4—C3	120.26 (17)	N2—C16—O2	118.93 (15)
C5—C4—H4	119.9	N2—C16—C15	125.40 (15)
C3—C4—H4	119.9	O2—C16—C15	115.64 (14)
C4—C5—C6	120.40 (17)	N2—C17—C18	118.43 (15)
C4—C5—H5	119.8	N2—C17—C22	122.48 (15)
C6—C5—H5	119.8	C18—C17—C22	119.09 (16)
C1—C6—C5	118.99 (16)	C19—C18—C17	120.17 (16)
C1—C6—C7	118.19 (15)	C19—C18—H18	119.9
C5—C6—C7	122.80 (16)	C17—C18—H18	119.9
C8—C7—C6	117.51 (16)	C18—C19—C20	119.84 (16)
C8—C7—C10	122.36 (16)	C18—C19—H19	120.1
C6—C7—C10	120.09 (15)	C20—C19—H19	120.1
C7—C8—C9	120.31 (15)	C21—C20—C19	121.85 (16)
C7—C8—C12	119.88 (16)	C21—C20—Cl1	120.09 (14)
C9—C8—C12	119.78 (15)	C19—C20—Cl1	118.05 (13)
N1—C9—C8	122.86 (16)	C20—C21—C22	118.66 (16)
N1—C9—C11	116.28 (16)	C20—C21—H21	120.7
C8—C9—C11	120.83 (16)	C22—C21—H21	120.7
C7—C10—H10A	109.5	C21—C22—C17	120.28 (15)
C7—C10—H10B	109.5	C21—C22—C23	122.08 (15)
H10A—C10—H10B	109.5	C17—C22—C23	117.62 (15)
C7—C10—H10C	109.5	C15—C23—C22	120.13 (15)
H10A—C10—H10C	109.5	C15—C23—H23	119.9
H10B—C10—H10C	109.5	C22—C23—H23	119.9
C9—C11—H11A	109.5	O2—C24—H24A	109.5
C9—C11—H11B	109.5	O2—C24—H24B	109.5
H11A—C11—H11B	109.5	H24A—C24—H24B	109.5
C9—C11—H11C	109.5	O2—C24—H24C	109.5
H11A—C11—H11C	109.5	H24A—C24—H24C	109.5
H11B—C11—H11C	109.5	H24B—C24—H24C	109.5

C9—N1—C1—C6	−1.2 (2)	C8—C12—C13—C14	2.2 (3)
C9—N1—C1—C2	177.38 (15)	C12—C13—C14—C15	−177.90 (16)
N1—C1—C2—C3	−179.95 (16)	C13—C14—C15—C23	35.7 (3)
C6—C1—C2—C3	−1.3 (2)	C13—C14—C15—C16	−146.59 (18)
C1—C2—C3—C4	−0.9 (3)	C17—N2—C16—O2	179.06 (14)
C2—C3—C4—C5	1.8 (3)	C17—N2—C16—C15	1.2 (2)
C3—C4—C5—C6	−0.6 (3)	C24—O2—C16—N2	3.1 (2)
N1—C1—C6—C5	−178.96 (16)	C24—O2—C16—C15	−178.80 (16)
C2—C1—C6—C5	2.5 (2)	C23—C15—C16—N2	−1.9 (2)
N1—C1—C6—C7	2.7 (2)	C14—C15—C16—N2	−179.71 (16)
C2—C1—C6—C7	−175.86 (15)	C23—C15—C16—O2	−179.79 (14)
C4—C5—C6—C1	−1.5 (3)	C14—C15—C16—O2	2.4 (2)
C4—C5—C6—C7	176.70 (17)	C16—N2—C17—C18	−178.75 (15)
C1—C6—C7—C8	−2.4 (2)	C16—N2—C17—C22	0.8 (2)
C5—C6—C7—C8	179.40 (16)	N2—C17—C18—C19	−177.67 (16)
C1—C6—C7—C10	175.34 (15)	C22—C17—C18—C19	2.7 (2)
C5—C6—C7—C10	−2.9 (2)	C17—C18—C19—C20	0.3 (3)
C6—C7—C8—C9	0.7 (2)	C18—C19—C20—C21	−2.3 (3)
C10—C7—C8—C9	−176.92 (16)	C18—C19—C20—Cl1	176.79 (14)
C6—C7—C8—C12	178.51 (14)	C19—C20—C21—C22	1.2 (3)
C10—C7—C8—C12	0.9 (2)	Cl1—C20—C21—C22	−177.88 (12)
C1—N1—C9—C8	−0.6 (2)	C20—C21—C22—C17	1.9 (2)
C1—N1—C9—C11	−178.50 (16)	C20—C21—C22—C23	−179.54 (15)
C7—C8—C9—N1	0.8 (3)	N2—C17—C22—C21	176.60 (15)
C12—C8—C9—N1	−176.98 (15)	C18—C17—C22—C21	−3.8 (2)
C7—C8—C9—C11	178.64 (17)	N2—C17—C22—C23	−2.0 (2)
C12—C8—C9—C11	0.8 (2)	C18—C17—C22—C23	177.52 (15)
C7—C8—C12—O1	−72.2 (2)	C16—C15—C23—C22	0.5 (2)
C9—C8—C12—O1	105.6 (2)	C14—C15—C23—C22	178.25 (15)
C7—C8—C12—C13	105.55 (19)	C21—C22—C23—C15	−177.31 (15)
C9—C8—C12—C13	−76.6 (2)	C17—C22—C23—C15	1.3 (2)
O1—C12—C13—C14	179.89 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O1ⁱ	0.98	2.52	3.221 (2)	129

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O1ⁱ	0.98	2.52	3.221 (2)	129

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

Footnotes

‡Additional correspondence author, e-mail: prasad24487@yahoo.co.in.

Acknowledgements

RP gratefully acknowledges the Council of Scientific and Industrial Research (CSIR), India, for a Senior Research Fellowship [grant No. 09/919/(0014)/2012 EMR-I]. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (grant No. UM·C/HIR-MOHE/SC/03).

References

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(2E)-3-(6-Chloro-2-meth­­oxy­quinolin-3-yl)-1-(2,4-di­methyl­quinolin-3-yl)prop-2-en-1-one

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organic compounds

(2E)-3-(6-Chloro-2-methoxyquinolin-3-yl)-1-(2,4-dimethylquinolin-3-yl)prop-2-en-1-one