(2E)-3-(2-Chloro-8-methyl­quinolin-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/S1600536813019405

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1275

doi:10.1107/S1600536813019405

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(2E)-3-(2-Chloro-8-methylquinolin-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)

In the molecule of the title compound, C₂₄H₁₉ClN₂O, the terminal quinolinyl residues are close to perpendicular to each other [dihedral angle 83.72 (4)°]. The quinolinyl residues are connected by and inclined to the prop-2-en-1-one bridge, with the C_ar—C_ar—C—C (ar = aromatic) torsion angles being 71.01 (17) and 20.6 (2)°. The crystal structure features phenyl–carbonyl C—H⋯O interactions and π–π interactions between centrosymmetrically related quinolinyl residues [3.5341 (10) and 3.8719 (9) Å], which together lead to a three-dimensional architecture.

Related literature

For background to quinoline chalcones and for a related structure, see: Prasath et al. (2013 ).

Experimental

Crystal data

C₂₄H₁₉ClN₂O
M_r = 386.86
Triclinic, $[P \overline 1]$
a = 7.4150 (5) Å
b = 9.9045 (6) Å
c = 14.0696 (9) Å
α = 71.072 (5)°
β = 88.427 (5)°
γ = 72.552 (5)°
V = 929.66 (10) Å³
Z = 2
Cu Kα radiation
μ = 1.95 mm⁻¹
T = 100 K
0.25 × 0.25 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ) T_min = 0.853, T_max = 1.000
6846 measured reflections
3811 independent reflections
3587 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.095
S = 1.04
3811 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O1ⁱ	0.95	2.58	3.364 (2)	140
Symmetry code: (i) x-1, y+1, z.

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/S1600536813019405/hb7108sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813019405/hb7108Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813019405/hb7108Isup3.cml

checkCIF report

Comment top

For the background to biological activities, utility as intermediates in organic synthesis and photophysical properties of quinolines, as well as the bio-activities of quinolinyl chalcones and a related structure, see the Introduction to Prasath et al. (2013).

In (I), Fig. 1, the dihedral angle between the quinolinyl rings is 83.72 (4)°. The conformation about the ethylene bond [C13═C14 = 1.3333 (19) Å] is E. The central prop-2-en-1-one residue, comprising the O1 and C12–C15 atoms, is twisted, as manifested in the O1—C12—C13—C14 torsion angle of 16.4 (2)°. The N1- and N2-containing quinolinyl rings are also twisted with respect to the central bridge, as seen in the C7—C8—C12—C13 and C13—C14—C15—C23 torsion angles of 71.01 (17) and 20.6 (2)°, respectively.

In the most closely related structure available for comparison, (II), namely (2E)-3-(6-chloro-2-methoxyquinolin-3-yl)-1-(5,7-dimethylquinolin-6-yl)prop-2-en-1-one (Prasath et al., 2013), the dihedral angle between the quinolinyl residues is 63.30 (5)°, indicating a more compact configuration than that in (I); the central residue in (II) is planar. Finally, when the structures are viewed normal to the ethylene bond, the pyridyl-N atoms in (I) can be described as anti, whereas they are closer to syn in (II).

In the crystal, linear supramolecular chains are formed by phenyl-C—H···O(carbonyl) interactions, Table 1. These, along with π–π interactions between the rings of centrosymmetrically related N1-quinolinyl residues [3.7578 (9) Å; angle of inclination = 1.91 (7)° for symmetry operation 1 - x, -y, 1 - z] and between the rings of centrosymmetrically related N2-quinolinyl residues [3.5767 (9) Å; angle of inclination = 0.99 (7)° for symmetry operation -x, 2 - y, -z], connect the molecules into a three-dimensional architecture, Fig. 2.

Related literature top

For background to quinoline chalcones and for a related structure, see: Prasath et al. (2013).

Experimental top

A mixture of 2,4-dimethyl-3-acetylquinoline (200 mg, 0.001 M) and 2-chloro-8-methylquinoline-3-carbaldehyde (200 mg, 0.001 M) in methanol (20 ml) containing 0.2 g of potassium hydroxide was stirred at room temperature for 12 h. Then 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 (1:1) mixture to afford (I). Re-crystallization was by slow evaporation of an acetone solution of (I), which yielded pale-yellow blocks in 78% yield; m.p. 458–460 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-(2-Chloro-8-methylquinolin-3-yl)-1-(2,4-dimethylquinolin-3-yl)prop-2-en-1-one top

Crystal data top

C₂₄H₁₉ClN₂O	Z = 2
M_r = 386.86	F(000) = 404
Triclinic, P1	D_x = 1.382 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 7.4150 (5) Å	Cell parameters from 4165 reflections
b = 9.9045 (6) Å	θ = 3.3–76.5°
c = 14.0696 (9) Å	µ = 1.95 mm⁻¹
α = 71.072 (5)°	T = 100 K
β = 88.427 (5)°	Block, pale-yellow
γ = 72.552 (5)°	0.25 × 0.25 × 0.25 mm
V = 929.66 (10) Å³

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	3811 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3587 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.014
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.7°, θ_min = 3.3°
ω scans	h = −9→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −12→11
T_min = 0.853, T_max = 1.000	l = −17→17
6846 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0508P)² + 0.4107P] where P = (F_o² + 2F_c²)/3
3811 reflections	(Δ/σ)_max < 0.001
256 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₄H₁₉ClN₂O	γ = 72.552 (5)°
M_r = 386.86	V = 929.66 (10) Å³
Triclinic, P1	Z = 2
a = 7.4150 (5) Å	Cu Kα radiation
b = 9.9045 (6) Å	µ = 1.95 mm⁻¹
c = 14.0696 (9) Å	T = 100 K
α = 71.072 (5)°	0.25 × 0.25 × 0.25 mm
β = 88.427 (5)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	3811 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	3587 reflections with I > 2σ(I)
T_min = 0.853, T_max = 1.000	R_int = 0.014
6846 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.04	Δρ_max = 0.30 e Å⁻³
3811 reflections	Δρ_min = −0.30 e Å⁻³
256 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	0.50310 (4)	0.74397 (4)	−0.07296 (2)	0.02306 (10)
O1	0.77211 (15)	0.37500 (12)	0.27778 (8)	0.0303 (2)
N1	0.59497 (15)	0.23114 (12)	0.58173 (8)	0.0197 (2)
N2	0.27853 (15)	0.99608 (13)	−0.06433 (8)	0.0204 (2)
C1	0.45484 (18)	0.16757 (15)	0.57864 (10)	0.0191 (3)
C2	0.40578 (19)	0.08004 (16)	0.67102 (10)	0.0230 (3)
H2	0.4675	0.0690	0.7326	0.028*
C3	0.2705 (2)	0.01120 (16)	0.67258 (11)	0.0248 (3)
H3	0.2387	−0.0471	0.7351	0.030*
C4	0.1783 (2)	0.02640 (16)	0.58199 (11)	0.0250 (3)
H4	0.0863	−0.0233	0.5835	0.030*
C5	0.22039 (19)	0.11248 (15)	0.49156 (10)	0.0222 (3)
H5	0.1563	0.1227	0.4309	0.027*
C6	0.35811 (18)	0.18627 (14)	0.48764 (10)	0.0187 (3)
C7	0.40656 (18)	0.27748 (14)	0.39547 (10)	0.0191 (3)
C8	0.55043 (18)	0.33647 (14)	0.40032 (10)	0.0192 (3)
C9	0.64203 (18)	0.31126 (14)	0.49597 (10)	0.0189 (3)
C10	0.3031 (2)	0.30187 (16)	0.29759 (10)	0.0234 (3)
H10A	0.3453	0.3727	0.2423	0.035*
H10B	0.1664	0.3426	0.3016	0.035*
H10C	0.3304	0.2061	0.2853	0.035*
C11	0.79125 (19)	0.38402 (16)	0.50126 (11)	0.0232 (3)
H11A	0.8428	0.3514	0.5713	0.035*
H11B	0.7346	0.4933	0.4766	0.035*
H11C	0.8934	0.3547	0.4594	0.035*
C12	0.61717 (19)	0.42581 (16)	0.30561 (10)	0.0219 (3)
C13	0.4853 (2)	0.57651 (16)	0.25090 (10)	0.0233 (3)
H13	0.3830	0.6205	0.2844	0.028*
C14	0.50609 (19)	0.65201 (16)	0.15594 (10)	0.0216 (3)
H14	0.6057	0.6040	0.1228	0.026*
C15	0.38631 (18)	0.80355 (15)	0.09910 (10)	0.0204 (3)
C16	0.37602 (18)	0.86237 (15)	−0.00807 (10)	0.0198 (3)
C17	0.17413 (18)	1.09272 (15)	−0.01732 (10)	0.0203 (3)
C18	0.06749 (19)	1.24027 (16)	−0.07813 (11)	0.0226 (3)
C19	−0.0346 (2)	1.33729 (16)	−0.03049 (12)	0.0261 (3)
H19	−0.1056	1.4363	−0.0702	0.031*
C20	−0.0373 (2)	1.29435 (17)	0.07542 (12)	0.0264 (3)
H20	−0.1087	1.3644	0.1057	0.032*
C21	0.0626 (2)	1.15243 (17)	0.13450 (11)	0.0243 (3)
H21	0.0597	1.1235	0.2057	0.029*
C22	0.17080 (19)	1.04805 (16)	0.08914 (10)	0.0209 (3)
C23	0.27938 (19)	0.90076 (16)	0.14569 (10)	0.0213 (3)
H23	0.2790	0.8678	0.2171	0.026*
C24	0.0660 (2)	1.28611 (17)	−0.19129 (11)	0.0274 (3)
H24A	−0.0111	1.3913	−0.2211	0.041*
H24B	0.0120	1.2227	−0.2151	0.041*
H24C	0.1959	1.2741	−0.2113	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02514 (17)	0.02405 (17)	0.01915 (17)	−0.00578 (13)	0.00524 (12)	−0.00798 (12)
O1	0.0269 (5)	0.0329 (6)	0.0264 (5)	−0.0062 (4)	0.0094 (4)	−0.0069 (4)
N1	0.0197 (5)	0.0203 (5)	0.0189 (5)	−0.0053 (4)	0.0017 (4)	−0.0067 (4)
N2	0.0193 (5)	0.0222 (6)	0.0213 (5)	−0.0090 (4)	0.0033 (4)	−0.0071 (5)
C1	0.0180 (6)	0.0184 (6)	0.0198 (6)	−0.0032 (5)	0.0017 (5)	−0.0072 (5)
C2	0.0235 (6)	0.0255 (7)	0.0181 (6)	−0.0068 (5)	0.0009 (5)	−0.0053 (5)
C3	0.0241 (7)	0.0251 (7)	0.0213 (7)	−0.0078 (6)	0.0041 (5)	−0.0028 (5)
C4	0.0221 (6)	0.0243 (7)	0.0276 (7)	−0.0091 (5)	0.0018 (5)	−0.0055 (6)
C5	0.0209 (6)	0.0218 (6)	0.0230 (7)	−0.0056 (5)	−0.0006 (5)	−0.0069 (5)
C6	0.0181 (6)	0.0175 (6)	0.0190 (6)	−0.0023 (5)	0.0017 (5)	−0.0069 (5)
C7	0.0195 (6)	0.0176 (6)	0.0180 (6)	−0.0015 (5)	0.0011 (5)	−0.0067 (5)
C8	0.0200 (6)	0.0174 (6)	0.0182 (6)	−0.0029 (5)	0.0038 (5)	−0.0059 (5)
C9	0.0181 (6)	0.0177 (6)	0.0196 (6)	−0.0026 (5)	0.0026 (5)	−0.0073 (5)
C10	0.0255 (7)	0.0241 (7)	0.0189 (6)	−0.0072 (5)	−0.0004 (5)	−0.0052 (5)
C11	0.0212 (6)	0.0235 (7)	0.0256 (7)	−0.0079 (5)	0.0027 (5)	−0.0083 (5)
C12	0.0236 (6)	0.0238 (7)	0.0195 (6)	−0.0092 (5)	0.0037 (5)	−0.0073 (5)
C13	0.0255 (7)	0.0225 (7)	0.0218 (6)	−0.0082 (5)	0.0052 (5)	−0.0065 (5)
C14	0.0221 (6)	0.0239 (7)	0.0208 (6)	−0.0093 (5)	0.0041 (5)	−0.0080 (5)
C15	0.0198 (6)	0.0224 (7)	0.0210 (6)	−0.0109 (5)	0.0031 (5)	−0.0061 (5)
C16	0.0191 (6)	0.0225 (6)	0.0207 (6)	−0.0096 (5)	0.0042 (5)	−0.0083 (5)
C17	0.0174 (6)	0.0220 (7)	0.0243 (7)	−0.0101 (5)	0.0033 (5)	−0.0079 (5)
C18	0.0200 (6)	0.0233 (7)	0.0260 (7)	−0.0107 (5)	0.0023 (5)	−0.0066 (5)
C19	0.0212 (6)	0.0216 (7)	0.0355 (8)	−0.0074 (5)	0.0018 (6)	−0.0087 (6)
C20	0.0222 (6)	0.0275 (7)	0.0362 (8)	−0.0107 (6)	0.0080 (6)	−0.0172 (6)
C21	0.0235 (7)	0.0296 (7)	0.0274 (7)	−0.0150 (6)	0.0076 (5)	−0.0134 (6)
C22	0.0196 (6)	0.0244 (7)	0.0239 (7)	−0.0126 (5)	0.0044 (5)	−0.0096 (5)
C23	0.0225 (6)	0.0252 (7)	0.0199 (6)	−0.0134 (5)	0.0039 (5)	−0.0072 (5)
C24	0.0267 (7)	0.0250 (7)	0.0262 (7)	−0.0073 (6)	0.0006 (6)	−0.0036 (6)

Geometric parameters (Å, º) top

Cl1—C16	1.7554 (14)	C11—H11A	0.9800
O1—C12	1.2177 (17)	C11—H11B	0.9800
N1—C9	1.3150 (17)	C11—H11C	0.9800
N1—C1	1.3749 (17)	C12—C13	1.4825 (19)
N2—C16	1.2963 (18)	C13—C14	1.3333 (19)
N2—C17	1.3752 (18)	C13—H13	0.9500
C1—C6	1.4161 (18)	C14—C15	1.4636 (19)
C1—C2	1.4161 (18)	C14—H14	0.9500
C2—C3	1.368 (2)	C15—C23	1.3814 (19)
C2—H2	0.9500	C15—C16	1.4243 (18)
C3—C4	1.406 (2)	C17—C22	1.4193 (19)
C3—H3	0.9500	C17—C18	1.423 (2)
C4—C5	1.370 (2)	C18—C19	1.378 (2)
C4—H4	0.9500	C18—C24	1.507 (2)
C5—C6	1.4136 (19)	C19—C20	1.412 (2)
C5—H5	0.9500	C19—H19	0.9500
C6—C7	1.4269 (18)	C20—C21	1.366 (2)
C7—C8	1.3739 (19)	C20—H20	0.9500
C7—C10	1.5082 (18)	C21—C22	1.4221 (19)
C8—C9	1.4371 (18)	C21—H21	0.9500
C8—C12	1.5050 (18)	C22—C23	1.410 (2)
C9—C11	1.5055 (18)	C23—H23	0.9500
C10—H10A	0.9800	C24—H24A	0.9800
C10—H10B	0.9800	C24—H24B	0.9800
C10—H10C	0.9800	C24—H24C	0.9800

C9—N1—C1	118.17 (11)	O1—C12—C8	120.60 (12)
C16—N2—C17	117.78 (12)	C13—C12—C8	116.16 (11)
N1—C1—C6	122.93 (12)	C14—C13—C12	121.82 (13)
N1—C1—C2	118.08 (12)	C14—C13—H13	119.1
C6—C1—C2	119.00 (12)	C12—C13—H13	119.1
C3—C2—C1	120.74 (13)	C13—C14—C15	124.62 (13)
C3—C2—H2	119.6	C13—C14—H14	117.7
C1—C2—H2	119.6	C15—C14—H14	117.7
C2—C3—C4	120.19 (13)	C23—C15—C16	115.37 (12)
C2—C3—H3	119.9	C23—C15—C14	122.38 (12)
C4—C3—H3	119.9	C16—C15—C14	122.23 (12)
C5—C4—C3	120.42 (13)	N2—C16—C15	126.49 (13)
C5—C4—H4	119.8	N2—C16—Cl1	115.42 (10)
C3—C4—H4	119.8	C15—C16—Cl1	118.08 (10)
C4—C5—C6	120.68 (13)	N2—C17—C22	121.50 (13)
C4—C5—H5	119.7	N2—C17—C18	118.38 (12)
C6—C5—H5	119.7	C22—C17—C18	120.12 (13)
C5—C6—C1	118.94 (12)	C19—C18—C17	118.10 (13)
C5—C6—C7	122.83 (12)	C19—C18—C24	121.77 (13)
C1—C6—C7	118.22 (12)	C17—C18—C24	120.12 (13)
C8—C7—C6	117.71 (12)	C18—C19—C20	122.18 (14)
C8—C7—C10	122.91 (12)	C18—C19—H19	118.9
C6—C7—C10	119.36 (12)	C20—C19—H19	118.9
C7—C8—C9	120.42 (12)	C21—C20—C19	120.24 (13)
C7—C8—C12	120.60 (12)	C21—C20—H20	119.9
C9—C8—C12	118.97 (12)	C19—C20—H20	119.9
N1—C9—C8	122.49 (12)	C20—C21—C22	119.83 (13)
N1—C9—C11	117.30 (12)	C20—C21—H21	120.1
C8—C9—C11	120.14 (12)	C22—C21—H21	120.1
C7—C10—H10A	109.5	C23—C22—C17	117.73 (13)
C7—C10—H10B	109.5	C23—C22—C21	122.75 (13)
H10A—C10—H10B	109.5	C17—C22—C21	119.52 (13)
C7—C10—H10C	109.5	C15—C23—C22	121.13 (12)
H10A—C10—H10C	109.5	C15—C23—H23	119.4
H10B—C10—H10C	109.5	C22—C23—H23	119.4
C9—C11—H11A	109.5	C18—C24—H24A	109.5
C9—C11—H11B	109.5	C18—C24—H24B	109.5
H11A—C11—H11B	109.5	H24A—C24—H24B	109.5
C9—C11—H11C	109.5	C18—C24—H24C	109.5
H11A—C11—H11C	109.5	H24A—C24—H24C	109.5
H11B—C11—H11C	109.5	H24B—C24—H24C	109.5
O1—C12—C13	123.24 (12)

C9—N1—C1—C6	−0.82 (19)	O1—C12—C13—C14	16.4 (2)
C9—N1—C1—C2	179.35 (12)	C8—C12—C13—C14	−164.32 (13)
N1—C1—C2—C3	−178.51 (12)	C12—C13—C14—C15	−177.18 (12)
C6—C1—C2—C3	1.7 (2)	C13—C14—C15—C23	20.6 (2)
C1—C2—C3—C4	0.1 (2)	C13—C14—C15—C16	−161.14 (13)
C2—C3—C4—C5	−1.3 (2)	C17—N2—C16—C15	0.2 (2)
C3—C4—C5—C6	0.6 (2)	C17—N2—C16—Cl1	179.09 (9)
C4—C5—C6—C1	1.2 (2)	C23—C15—C16—N2	0.5 (2)
C4—C5—C6—C7	−179.81 (13)	C14—C15—C16—N2	−177.91 (12)
N1—C1—C6—C5	177.89 (12)	C23—C15—C16—Cl1	−178.36 (9)
C2—C1—C6—C5	−2.28 (19)	C14—C15—C16—Cl1	3.26 (17)
N1—C1—C6—C7	−1.16 (19)	C16—N2—C17—C22	−0.64 (19)
C2—C1—C6—C7	178.67 (12)	C16—N2—C17—C18	179.55 (11)
C5—C6—C7—C8	−176.23 (12)	N2—C17—C18—C19	−179.07 (12)
C1—C6—C7—C8	2.78 (18)	C22—C17—C18—C19	1.12 (19)
C5—C6—C7—C10	2.20 (19)	N2—C17—C18—C24	1.80 (19)
C1—C6—C7—C10	−178.79 (12)	C22—C17—C18—C24	−178.01 (12)
C6—C7—C8—C9	−2.55 (19)	C17—C18—C19—C20	−0.5 (2)
C10—C7—C8—C9	179.08 (12)	C24—C18—C19—C20	178.63 (13)
C6—C7—C8—C12	176.23 (11)	C18—C19—C20—C21	−0.4 (2)
C10—C7—C8—C12	−2.1 (2)	C19—C20—C21—C22	0.5 (2)
C1—N1—C9—C8	1.12 (19)	N2—C17—C22—C23	0.34 (19)
C1—N1—C9—C11	178.05 (11)	C18—C17—C22—C23	−179.86 (11)
C7—C8—C9—N1	0.6 (2)	N2—C17—C22—C21	179.24 (11)
C12—C8—C9—N1	−178.20 (12)	C18—C17—C22—C21	−0.95 (19)
C7—C8—C9—C11	−176.24 (12)	C20—C21—C22—C23	178.96 (12)
C12—C8—C9—C11	4.96 (18)	C20—C21—C22—C17	0.12 (19)
C7—C8—C12—O1	−109.66 (16)	C16—C15—C23—C22	−0.77 (18)
C9—C8—C12—O1	69.14 (18)	C14—C15—C23—C22	177.61 (12)
C7—C8—C12—C13	71.01 (17)	C17—C22—C23—C15	0.40 (19)
C9—C8—C12—C13	−110.19 (14)	C21—C22—C23—C15	−178.47 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O1ⁱ	0.95	2.58	3.364 (2)	140

Symmetry code: (i) x−1, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O1ⁱ	0.95	2.58	3.364 (2)	140

Symmetry code: (i) x−1, y+1, z.

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

Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Prasath, R., Sarveswari, S., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o1274. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 8| August 2013| Page o1275

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

(2E)-3-(2-Chloro-8-methyl­quinolin-3-yl)-1-(2,4-di­methyl­quinolin-3-yl)prop-2-en-1-one

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organic compounds

(2E)-3-(2-Chloro-8-methylquinolin-3-yl)-1-(2,4-dimethylquinolin-3-yl)prop-2-en-1-one