(2E)-1-(6-Chloro-2-methyl-4-phenyl­quinolin-3-yl)-3-(4-chloro­phen­yl)prop-2-en-1-one

Sarveswari, S.; Vijayakumar, V.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811004740

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o624

doi:10.1107/S1600536811004740

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(2E)-1-(6-Chloro-2-methyl-4-phenylquinolin-3-yl)-3-(4-chlorophenyl)prop-2-en-1-one

S. Sarveswari,^a V. Vijayakumar,^a ‡ Seik Weng Ng ^b and Edward R. T. Tiekink ^b ^*

^aOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, Tamilnadu, India, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 7 February 2011; accepted 8 February 2011; online 12 February 2011)

Two independent molecules comprise the asymmetric unit of the title chalcone, C₂₅H₁₇Cl₂NO, and while each has an E configuration about the ethylene double bond, they differ in the relative orientations of the carbonyl and ethylene double bonds within the prop-2-en-1-one residues, i.e. anti and syn. For each molecule, the benzene [dihedral angles = 71.04 (9) and 73.34 (12)°] and prop-2-en-1-one [C—C—C—O = 91.2 (2) and −119.1 (3)°] substituents are twisted out of the plane of the quinoline moiety to which they are attached. The crystal structure is stabilized by C—H⋯π and π–π [Cg(quinoline)⋯Cg(quinoline) = 3.7809 (12) and 3.8446 (11) Å] interactions.

Related literature

For background to chalcone chemistry, see: Roman (2004 ). For related structures, see: Prasath et al. (2010 ); Reddy et al. (2010 ).

Experimental

Crystal data

C₂₅H₁₇Cl₂NO
M_r = 418.30
Triclinic, $[P \overline 1]$
a = 11.1704 (3) Å
b = 12.8497 (5) Å
c = 16.0591 (6) Å
α = 74.914 (3)°
β = 80.603 (3)°
γ = 70.789 (3)°
V = 2094.05 (13) Å³
Z = 4
Cu Kα radiation
μ = 2.91 mm⁻¹
T = 295 K
0.30 × 0.30 × 0.10 mm

Data collection

Agilent Supernova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.574, T_max = 1.000
14958 measured reflections
8252 independent reflections
7088 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.158
S = 1.03
8252 reflections
525 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C20–C25 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C38—H38⋯Cg1ⁱ	0.93	2.93	3.458 (3)	117
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010); 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 (Farrugia, 1997 ) 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/S1600536811004740/hg2798sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811004740/hg2798Isup2.hkl

checkCIF report

Comment top

Chalcones and its analogs are valuable intermediates in organic synthesis and exhibit a multitude of biological activities. From a chemical point of view, an important feature of chalcones and their heteroanalogs is the ability to act as activated unsaturated systems in conjugated addition reactions of carbanions in the presence of basic catalysts (Roman, 2004). The title compound, (I), was examined in continuation of our interest in the structural chemistry of chalcones (Prasath et al., 2010; Reddy et al., 2010).

Two independent molecules comprise the asymmetric unit of (I), one with an anti relationship between the carbonyl and ethylene double bonds, Fig. 1, and one with a syn relationship, Fig. 2. In each, the conformation about the ethylene bond [C18═C19 = 1.319 (3) Å and C43═C44 = 1.328 (3) Å] is E. For both molecules, the benzene ring is twisted out of the plane of the quinoline residue to which it is connected; the C6—C7—C11—C12 and C31—C32—C36—C37 torsion angles are -69.0 (2) and -107.1 (2) °, respectively. The prop-2-en-1-one substituents are also twisted out of the plane of the respective quinoline residues as seen in the values of the C7—C8—C17—O1 and C32—C33—C42—O2 torsion angles of 91.2 (2) and -119.1 (3) °, respectively. Within the prop-2-en-1-one substituents themselves, the terminal benzene rings are not co-planar with the C18—C19—C20—C21 and C43—C44—C45—C46 torsion angles being -159.6 (2) and -170.8 (2) °, respectively.

The molecules are stabilized in the crystal packing by a combination of C—H···π, π–π, and C—Cl···π interactions. The C—H···π contacts, Table 1, occur between the two molecules comprising the asymmetric unit. The π–π interactions occur between centrosymmetrically related quinoline rings belonging to like molecules [Cg(N1,C1,C6—C9)···Cg(C1—C6)ⁱⁱ = 3.8446 (11) ° for ii: 1 - x, 1 - y, -z; and Cg(N2,C26,C31—C34)···Cg(C26—C31)ⁱⁱⁱ = 3.7809 (12) ° for iii: 1 - x, 1 - y, 1 - z]. The C—H···Cl contacts [C4—Cl1···Cg(C20—C25)^iv = 3.6082 (13) Å and angle at Cl1 = 116.34 (7) ° for iv: -1 + x, y, z] also occur between like molecules. A view of the crystal packing is shown in Fig. 3.

Related literature top

For background to chalcone chemistry, see: Roman (2004). For related structures, see: Prasath et al. (2010); Reddy et al. (2010).

Experimental top

A mixture of 3-acetyl-6-chloro-2-methyl-4-phenylquinoline (3.1 g, 0.01 M) and 4-chlorobenzaldehyde (1.4 g, 0.01 M) and a catalytic amount of KOH in distilled ethanol (40 ml) was stirred for about 12 h. The resulting mixture was concentrated to remove ethanol, poured onto ice and neutralized with dilute acetic acid. The resultant solid was filtered, dried and purified by column chromatography using a 1:1 mixture of ethyl acetate and petroleum ether. Recrystallization was from acetone; Yield: 64% and m.pt: 397–399 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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).

Figures top

	Fig. 1. The molecular structure of the first independent molecule of (I), i.e. the anti form, showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.
	Fig. 2. The molecular structure of the second independent molecule of (I), i.e. the syn form, showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.
	Fig. 3. A view in projection down the c axis of the unit-cell contents of (I). The C—H···π, π–π, and C—Cl···π interactions are shown as purple, orange and green dashed lines, respectively.

(2E)-1-(6-Chloro-2-methyl-4-phenylquinolin-3-yl)- 3-(4-chlorophenyl)prop-2-en-1-one top

Crystal data top

C₂₅H₁₇Cl₂NO	Z = 4
M_r = 418.30	F(000) = 864
Triclinic, P1	D_x = 1.327 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 11.1704 (3) Å	Cell parameters from 8901 reflections
b = 12.8497 (5) Å	θ = 2.9–74.1°
c = 16.0591 (6) Å	µ = 2.91 mm⁻¹
α = 74.914 (3)°	T = 295 K
β = 80.603 (3)°	Prism, colourless
γ = 70.789 (3)°	0.30 × 0.30 × 0.10 mm
V = 2094.05 (13) Å³

Data collection top

Agilent Supernova Dual diffractometer with an Atlas detector	8252 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	7088 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.026
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.3°, θ_min = 2.9°
ω scans	h = −11→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −16→15
T_min = 0.574, T_max = 1.000	l = −20→19
14958 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0899P)² + 0.4585P] where P = (F_o² + 2F_c²)/3
8252 reflections	(Δ/σ)_max = 0.001
525 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₂₅H₁₇Cl₂NO	γ = 70.789 (3)°
M_r = 418.30	V = 2094.05 (13) Å³
Triclinic, P1	Z = 4
a = 11.1704 (3) Å	Cu Kα radiation
b = 12.8497 (5) Å	µ = 2.91 mm⁻¹
c = 16.0591 (6) Å	T = 295 K
α = 74.914 (3)°	0.30 × 0.30 × 0.10 mm
β = 80.603 (3)°

Data collection top

Agilent Supernova Dual diffractometer with an Atlas detector	8252 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	7088 reflections with I > 2σ(I)
T_min = 0.574, T_max = 1.000	R_int = 0.026
14958 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.03	Δρ_max = 0.43 e Å⁻³
8252 reflections	Δρ_min = −0.41 e Å⁻³
525 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	0.16358 (5)	0.49560 (5)	0.26030 (4)	0.06920 (17)
Cl2	1.33991 (8)	0.11218 (7)	0.45986 (5)	0.0924 (2)
O1	0.86575 (14)	0.22234 (15)	0.02125 (11)	0.0691 (4)
N1	0.61911 (15)	0.56418 (13)	0.04091 (10)	0.0501 (4)
C1	0.51604 (16)	0.54394 (15)	0.09308 (11)	0.0443 (4)
C2	0.40157 (18)	0.63350 (16)	0.09149 (13)	0.0512 (4)
H2	0.3986	0.7037	0.0554	0.061*
C3	0.29485 (18)	0.61886 (17)	0.14218 (14)	0.0541 (4)
H3	0.2196	0.6783	0.1404	0.065*
C4	0.30038 (17)	0.51310 (16)	0.19691 (13)	0.0501 (4)
C5	0.40840 (17)	0.42366 (16)	0.20038 (12)	0.0486 (4)
H5	0.4092	0.3542	0.2370	0.058*
C6	0.51918 (16)	0.43729 (14)	0.14790 (11)	0.0433 (4)
C7	0.63491 (17)	0.34658 (15)	0.14543 (12)	0.0463 (4)
C8	0.73523 (17)	0.36816 (16)	0.08963 (12)	0.0486 (4)
C9	0.72457 (17)	0.47965 (17)	0.03906 (13)	0.0503 (4)
C10	0.8367 (2)	0.5062 (2)	−0.01747 (17)	0.0686 (6)
H10A	0.8075	0.5746	−0.0603	0.103*
H10B	0.8815	0.4452	−0.0456	0.103*
H10C	0.8926	0.5159	0.0174	0.103*
C11	0.64371 (16)	0.23274 (15)	0.20244 (13)	0.0485 (4)
C12	0.6432 (2)	0.21729 (18)	0.29087 (14)	0.0595 (5)
H12	0.6381	0.2775	0.3146	0.071*
C13	0.6502 (2)	0.11177 (19)	0.34435 (16)	0.0692 (6)
H13	0.6508	0.1012	0.4038	0.083*
C14	0.6564 (2)	0.02285 (19)	0.30963 (16)	0.0675 (6)
H14	0.6597	−0.0474	0.3458	0.081*
C15	0.6575 (2)	0.03717 (19)	0.22225 (17)	0.0665 (6)
H15	0.6624	−0.0234	0.1990	0.080*
C16	0.6514 (2)	0.14203 (18)	0.16806 (15)	0.0584 (5)
H16	0.6524	0.1515	0.1086	0.070*
C17	0.85560 (18)	0.27261 (18)	0.07789 (13)	0.0542 (4)
C18	0.95710 (19)	0.2412 (2)	0.13521 (15)	0.0622 (5)
H18	1.0323	0.1867	0.1230	0.075*
C19	0.95068 (19)	0.28387 (19)	0.20273 (14)	0.0601 (5)
H19	0.8771	0.3412	0.2127	0.072*
C20	1.0485 (2)	0.24950 (19)	0.26344 (14)	0.0597 (5)
C21	1.0179 (2)	0.2730 (2)	0.34513 (15)	0.0667 (6)
H21	0.9357	0.3158	0.3598	0.080*
C22	1.1072 (3)	0.2339 (2)	0.40532 (16)	0.0718 (6)
H22	1.0853	0.2496	0.4601	0.086*
C23	1.2288 (2)	0.1717 (2)	0.38295 (15)	0.0657 (5)
C24	1.2642 (2)	0.1516 (3)	0.30134 (17)	0.0769 (7)
H24	1.3477	0.1123	0.2862	0.092*
C25	1.1743 (2)	0.1906 (2)	0.24211 (16)	0.0747 (7)
H25	1.1981	0.1772	0.1867	0.090*
Cl3	0.90535 (6)	0.58126 (7)	0.40484 (4)	0.0849 (2)
Cl4	0.90415 (7)	−0.25246 (7)	1.15298 (5)	0.0979 (3)
O2	0.4659 (2)	0.17598 (16)	0.71587 (14)	0.0901 (6)
N2	0.45355 (15)	0.52142 (13)	0.63374 (11)	0.0513 (4)
C26	0.56090 (18)	0.53029 (15)	0.58190 (12)	0.0473 (4)
C27	0.5587 (2)	0.63632 (17)	0.52686 (14)	0.0595 (5)
H27	0.4852	0.6972	0.5274	0.071*
C28	0.6626 (2)	0.65091 (18)	0.47297 (14)	0.0641 (5)
H28	0.6597	0.7208	0.4365	0.077*
C29	0.7733 (2)	0.55961 (19)	0.47328 (13)	0.0578 (5)
C30	0.78037 (19)	0.45574 (18)	0.52438 (13)	0.0530 (4)
H30	0.8551	0.3963	0.5228	0.064*
C31	0.67341 (17)	0.43863 (15)	0.57993 (11)	0.0452 (4)
C32	0.67093 (17)	0.33154 (15)	0.63337 (12)	0.0474 (4)
C33	0.55979 (18)	0.32275 (16)	0.68166 (12)	0.0488 (4)
C34	0.45213 (18)	0.42134 (17)	0.68166 (12)	0.0500 (4)
C35	0.3321 (2)	0.4172 (2)	0.73827 (16)	0.0666 (6)
H35A	0.2747	0.4924	0.7340	0.100*
H35B	0.3519	0.3848	0.7972	0.100*
H35C	0.2929	0.3717	0.7198	0.100*
C36	0.78570 (19)	0.23100 (16)	0.63245 (14)	0.0545 (4)
C37	0.7881 (2)	0.1469 (2)	0.5930 (2)	0.0778 (7)
H37	0.7175	0.1524	0.5665	0.093*
C38	0.8959 (3)	0.0539 (2)	0.5930 (3)	0.1036 (11)
H38	0.8976	−0.0022	0.5657	0.124*
C39	0.9992 (3)	0.0443 (2)	0.6328 (3)	0.1048 (11)
H39	1.0704	−0.0188	0.6334	0.126*
C40	0.9983 (3)	0.1272 (3)	0.6717 (2)	0.0936 (9)
H40	1.0689	0.1204	0.6987	0.112*
C41	0.8928 (2)	0.2212 (2)	0.67094 (18)	0.0717 (6)
H41	0.8934	0.2783	0.6964	0.086*
C42	0.5465 (2)	0.21028 (17)	0.73280 (14)	0.0578 (5)
C43	0.6285 (2)	0.14702 (17)	0.80398 (13)	0.0555 (4)
H43	0.6941	0.1725	0.8115	0.067*
C44	0.6106 (2)	0.05441 (17)	0.85759 (14)	0.0565 (5)
H44	0.5444	0.0319	0.8470	0.068*
C45	0.68219 (19)	−0.01640 (16)	0.93118 (13)	0.0534 (4)
C46	0.6598 (2)	−0.11931 (18)	0.97154 (15)	0.0632 (5)
H46	0.5982	−0.1395	0.9523	0.076*
C47	0.7274 (2)	−0.19163 (19)	1.03947 (15)	0.0676 (6)
H47	0.7122	−0.2603	1.0655	0.081*
C48	0.8172 (2)	−0.1612 (2)	1.06821 (14)	0.0655 (6)
C49	0.8405 (2)	−0.0588 (2)	1.03070 (16)	0.0661 (5)
H49	0.9008	−0.0384	1.0513	0.079*
C50	0.7730 (2)	0.01233 (17)	0.96251 (14)	0.0599 (5)
H50	0.7886	0.0809	0.9370	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0485 (3)	0.0690 (3)	0.0810 (4)	−0.0169 (2)	0.0158 (2)	−0.0153 (3)
Cl2	0.1064 (5)	0.0972 (5)	0.0794 (4)	−0.0360 (4)	−0.0375 (4)	−0.0041 (4)
O1	0.0567 (8)	0.0792 (10)	0.0693 (9)	−0.0061 (7)	−0.0043 (7)	−0.0323 (8)
N1	0.0507 (8)	0.0490 (8)	0.0522 (8)	−0.0209 (7)	−0.0003 (7)	−0.0091 (7)
C1	0.0447 (9)	0.0438 (9)	0.0456 (9)	−0.0159 (7)	−0.0037 (7)	−0.0088 (7)
C2	0.0532 (10)	0.0413 (9)	0.0542 (10)	−0.0113 (8)	−0.0039 (8)	−0.0065 (8)
C3	0.0474 (10)	0.0469 (10)	0.0610 (11)	−0.0053 (8)	−0.0037 (8)	−0.0122 (8)
C4	0.0434 (9)	0.0515 (10)	0.0537 (10)	−0.0143 (8)	0.0019 (7)	−0.0124 (8)
C5	0.0472 (9)	0.0439 (9)	0.0513 (10)	−0.0137 (7)	0.0007 (7)	−0.0075 (7)
C6	0.0413 (8)	0.0424 (9)	0.0455 (9)	−0.0121 (7)	−0.0030 (7)	−0.0097 (7)
C7	0.0437 (9)	0.0446 (9)	0.0475 (9)	−0.0103 (7)	−0.0028 (7)	−0.0094 (7)
C8	0.0404 (9)	0.0526 (10)	0.0519 (10)	−0.0116 (7)	−0.0016 (7)	−0.0144 (8)
C9	0.0452 (9)	0.0573 (11)	0.0525 (10)	−0.0219 (8)	0.0014 (7)	−0.0142 (8)
C10	0.0540 (12)	0.0765 (14)	0.0781 (15)	−0.0321 (11)	0.0114 (10)	−0.0162 (12)
C11	0.0383 (8)	0.0429 (9)	0.0567 (10)	−0.0065 (7)	−0.0001 (7)	−0.0078 (8)
C12	0.0637 (12)	0.0496 (10)	0.0579 (11)	−0.0110 (9)	0.0003 (9)	−0.0107 (9)
C13	0.0793 (15)	0.0576 (12)	0.0578 (12)	−0.0157 (11)	−0.0012 (10)	0.0000 (10)
C14	0.0659 (13)	0.0482 (11)	0.0749 (14)	−0.0127 (9)	0.0006 (11)	−0.0002 (10)
C15	0.0656 (13)	0.0491 (11)	0.0833 (16)	−0.0167 (9)	0.0014 (11)	−0.0177 (10)
C16	0.0586 (11)	0.0534 (11)	0.0616 (12)	−0.0156 (9)	−0.0024 (9)	−0.0131 (9)
C17	0.0436 (9)	0.0602 (11)	0.0550 (11)	−0.0124 (8)	0.0025 (8)	−0.0146 (9)
C18	0.0435 (10)	0.0694 (13)	0.0672 (13)	−0.0024 (9)	−0.0036 (9)	−0.0237 (10)
C19	0.0473 (10)	0.0616 (12)	0.0645 (12)	−0.0061 (9)	−0.0003 (9)	−0.0182 (10)
C20	0.0565 (11)	0.0612 (12)	0.0596 (12)	−0.0132 (9)	−0.0025 (9)	−0.0176 (10)
C21	0.0698 (13)	0.0630 (13)	0.0652 (13)	−0.0134 (10)	0.0016 (10)	−0.0238 (11)
C22	0.0950 (17)	0.0696 (14)	0.0553 (12)	−0.0279 (13)	−0.0025 (11)	−0.0198 (11)
C23	0.0756 (14)	0.0624 (13)	0.0633 (13)	−0.0268 (11)	−0.0144 (11)	−0.0079 (10)
C24	0.0577 (13)	0.0975 (19)	0.0731 (15)	−0.0140 (12)	−0.0089 (11)	−0.0251 (14)
C25	0.0580 (12)	0.1000 (19)	0.0616 (13)	−0.0094 (12)	−0.0046 (10)	−0.0290 (13)
Cl3	0.0766 (4)	0.1135 (5)	0.0664 (3)	−0.0543 (4)	0.0053 (3)	0.0031 (3)
Cl4	0.0807 (4)	0.1019 (5)	0.0778 (4)	−0.0143 (4)	−0.0140 (3)	0.0241 (4)
O2	0.1015 (13)	0.0784 (11)	0.1015 (14)	−0.0568 (11)	−0.0422 (11)	0.0203 (10)
N2	0.0514 (8)	0.0475 (8)	0.0523 (8)	−0.0102 (7)	−0.0031 (7)	−0.0133 (7)
C26	0.0530 (10)	0.0436 (9)	0.0450 (9)	−0.0144 (7)	−0.0042 (7)	−0.0094 (7)
C27	0.0722 (13)	0.0430 (10)	0.0570 (11)	−0.0127 (9)	−0.0058 (9)	−0.0063 (8)
C28	0.0881 (15)	0.0506 (11)	0.0527 (11)	−0.0293 (11)	−0.0055 (10)	0.0007 (9)
C29	0.0638 (12)	0.0673 (12)	0.0469 (10)	−0.0331 (10)	−0.0024 (8)	−0.0049 (9)
C30	0.0489 (10)	0.0575 (11)	0.0525 (10)	−0.0187 (8)	−0.0034 (8)	−0.0090 (8)
C31	0.0475 (9)	0.0437 (9)	0.0455 (9)	−0.0164 (7)	−0.0043 (7)	−0.0080 (7)
C32	0.0471 (9)	0.0430 (9)	0.0516 (9)	−0.0144 (7)	−0.0070 (7)	−0.0068 (7)
C33	0.0512 (10)	0.0461 (9)	0.0491 (9)	−0.0185 (8)	−0.0069 (7)	−0.0039 (7)
C34	0.0487 (9)	0.0544 (10)	0.0476 (9)	−0.0170 (8)	−0.0034 (7)	−0.0110 (8)
C35	0.0556 (12)	0.0802 (15)	0.0641 (13)	−0.0249 (11)	0.0053 (10)	−0.0167 (11)
C36	0.0510 (10)	0.0442 (9)	0.0626 (11)	−0.0136 (8)	−0.0022 (8)	−0.0049 (8)
C37	0.0637 (13)	0.0593 (13)	0.114 (2)	−0.0181 (11)	−0.0014 (13)	−0.0297 (14)
C38	0.0825 (19)	0.0600 (15)	0.170 (3)	−0.0183 (14)	0.015 (2)	−0.0479 (19)
C39	0.0656 (17)	0.0584 (15)	0.164 (3)	0.0017 (12)	0.0044 (18)	−0.0139 (18)
C40	0.0580 (14)	0.0813 (18)	0.121 (3)	0.0008 (12)	−0.0186 (15)	−0.0100 (17)
C41	0.0559 (12)	0.0682 (14)	0.0839 (16)	−0.0075 (10)	−0.0137 (11)	−0.0146 (12)
C42	0.0596 (11)	0.0514 (10)	0.0620 (12)	−0.0247 (9)	−0.0069 (9)	−0.0008 (9)
C43	0.0590 (11)	0.0495 (10)	0.0567 (11)	−0.0203 (9)	−0.0040 (9)	−0.0048 (8)
C44	0.0571 (11)	0.0497 (10)	0.0600 (11)	−0.0191 (8)	−0.0023 (9)	−0.0055 (9)
C45	0.0554 (10)	0.0450 (9)	0.0525 (10)	−0.0126 (8)	0.0050 (8)	−0.0074 (8)
C46	0.0676 (13)	0.0562 (11)	0.0635 (12)	−0.0262 (10)	0.0025 (10)	−0.0044 (10)
C47	0.0739 (14)	0.0528 (11)	0.0627 (13)	−0.0189 (10)	0.0073 (10)	0.0020 (10)
C48	0.0588 (12)	0.0623 (12)	0.0542 (11)	−0.0054 (10)	0.0054 (9)	0.0002 (9)
C49	0.0602 (12)	0.0679 (13)	0.0653 (13)	−0.0170 (10)	−0.0036 (10)	−0.0104 (11)
C50	0.0640 (12)	0.0478 (10)	0.0628 (12)	−0.0167 (9)	−0.0024 (9)	−0.0055 (9)

Geometric parameters (Å, º) top

Cl1—C4	1.7382 (19)	Cl3—C29	1.744 (2)
Cl2—C23	1.742 (2)	Cl4—C48	1.739 (2)
O1—C17	1.217 (2)	O2—C42	1.218 (3)
N1—C9	1.316 (3)	N2—C34	1.319 (3)
N1—C1	1.365 (2)	N2—C26	1.363 (3)
C1—C2	1.410 (3)	C26—C27	1.413 (3)
C1—C6	1.416 (2)	C26—C31	1.414 (3)
C2—C3	1.368 (3)	C27—C28	1.364 (3)
C2—H2	0.9300	C27—H27	0.9300
C3—C4	1.401 (3)	C28—C29	1.397 (3)
C3—H3	0.9300	C28—H28	0.9300
C4—C5	1.362 (3)	C29—C30	1.358 (3)
C5—C6	1.413 (2)	C30—C31	1.412 (3)
C5—H5	0.9300	C30—H30	0.9300
C6—C7	1.431 (2)	C31—C32	1.426 (2)
C7—C8	1.372 (3)	C32—C33	1.374 (3)
C7—C11	1.492 (3)	C32—C36	1.492 (3)
C8—C9	1.428 (3)	C33—C34	1.431 (3)
C8—C17	1.517 (3)	C33—C42	1.506 (3)
C9—C10	1.503 (3)	C34—C35	1.501 (3)
C10—H10A	0.9600	C35—H35A	0.9600
C10—H10B	0.9600	C35—H35B	0.9600
C10—H10C	0.9600	C35—H35C	0.9600
C11—C12	1.381 (3)	C36—C37	1.379 (3)
C11—C16	1.387 (3)	C36—C41	1.390 (3)
C12—C13	1.388 (3)	C37—C38	1.390 (4)
C12—H12	0.9300	C37—H37	0.9300
C13—C14	1.374 (3)	C38—C39	1.364 (5)
C13—H13	0.9300	C38—H38	0.9300
C14—C15	1.365 (4)	C39—C40	1.364 (5)
C14—H14	0.9300	C39—H39	0.9300
C15—C16	1.388 (3)	C40—C41	1.382 (3)
C15—H15	0.9300	C40—H40	0.9300
C16—H16	0.9300	C41—H41	0.9300
C17—C18	1.464 (3)	C42—C43	1.474 (3)
C18—C19	1.319 (3)	C43—C44	1.328 (3)
C18—H18	0.9300	C43—H43	0.9300
C19—C20	1.465 (3)	C44—C45	1.461 (3)
C19—H19	0.9300	C44—H44	0.9300
C20—C21	1.386 (3)	C45—C50	1.389 (3)
C20—C25	1.394 (3)	C45—C46	1.396 (3)
C21—C22	1.384 (4)	C46—C47	1.380 (3)
C21—H21	0.9300	C46—H46	0.9300
C22—C23	1.375 (4)	C47—C48	1.369 (4)
C22—H22	0.9300	C47—H47	0.9300
C23—C24	1.371 (4)	C48—C49	1.387 (3)
C24—C25	1.377 (3)	C49—C50	1.378 (3)
C24—H24	0.9300	C49—H49	0.9300
C25—H25	0.9300	C50—H50	0.9300

C9—N1—C1	118.46 (16)	C34—N2—C26	118.56 (16)
N1—C1—C2	118.14 (16)	N2—C26—C27	118.09 (17)
N1—C1—C6	122.92 (16)	N2—C26—C31	123.31 (17)
C2—C1—C6	118.93 (16)	C27—C26—C31	118.60 (18)
C3—C2—C1	121.07 (17)	C28—C27—C26	121.1 (2)
C3—C2—H2	119.5	C28—C27—H27	119.4
C1—C2—H2	119.5	C26—C27—H27	119.4
C2—C3—C4	119.13 (17)	C27—C28—C29	119.23 (19)
C2—C3—H3	120.4	C27—C28—H28	120.4
C4—C3—H3	120.4	C29—C28—H28	120.4
C5—C4—C3	122.07 (17)	C30—C29—C28	122.08 (19)
C5—C4—Cl1	119.37 (15)	C30—C29—Cl3	119.69 (17)
C3—C4—Cl1	118.55 (14)	C28—C29—Cl3	118.22 (16)
C4—C5—C6	119.44 (17)	C29—C30—C31	119.53 (19)
C4—C5—H5	120.3	C29—C30—H30	120.2
C6—C5—H5	120.3	C31—C30—H30	120.2
C5—C6—C1	119.35 (16)	C30—C31—C26	119.43 (17)
C5—C6—C7	122.85 (16)	C30—C31—C32	123.25 (17)
C1—C6—C7	117.78 (15)	C26—C31—C32	117.30 (16)
C8—C7—C6	118.00 (16)	C33—C32—C31	118.61 (16)
C8—C7—C11	122.04 (16)	C33—C32—C36	121.53 (16)
C6—C7—C11	119.96 (15)	C31—C32—C36	119.79 (16)
C7—C8—C9	120.17 (16)	C32—C33—C34	119.91 (17)
C7—C8—C17	120.18 (17)	C32—C33—C42	121.42 (17)
C9—C8—C17	119.57 (16)	C34—C33—C42	118.64 (17)
N1—C9—C8	122.56 (16)	N2—C34—C33	122.17 (17)
N1—C9—C10	116.73 (18)	N2—C34—C35	116.12 (18)
C8—C9—C10	120.69 (18)	C33—C34—C35	121.69 (18)
C9—C10—H10A	109.5	C34—C35—H35A	109.5
C9—C10—H10B	109.5	C34—C35—H35B	109.5
H10A—C10—H10B	109.5	H35A—C35—H35B	109.5
C9—C10—H10C	109.5	C34—C35—H35C	109.5
H10A—C10—H10C	109.5	H35A—C35—H35C	109.5
H10B—C10—H10C	109.5	H35B—C35—H35C	109.5
C12—C11—C16	119.32 (19)	C37—C36—C41	118.8 (2)
C12—C11—C7	119.69 (17)	C37—C36—C32	120.9 (2)
C16—C11—C7	120.99 (18)	C41—C36—C32	120.26 (19)
C11—C12—C13	120.0 (2)	C36—C37—C38	120.0 (3)
C11—C12—H12	120.0	C36—C37—H37	120.0
C13—C12—H12	120.0	C38—C37—H37	120.0
C14—C13—C12	120.2 (2)	C39—C38—C37	120.4 (3)
C14—C13—H13	119.9	C39—C38—H38	119.8
C12—C13—H13	119.9	C37—C38—H38	119.8
C15—C14—C13	120.3 (2)	C40—C39—C38	120.2 (3)
C15—C14—H14	119.9	C40—C39—H39	119.9
C13—C14—H14	119.9	C38—C39—H39	119.9
C14—C15—C16	120.1 (2)	C39—C40—C41	120.1 (3)
C14—C15—H15	120.0	C39—C40—H40	119.9
C16—C15—H15	120.0	C41—C40—H40	119.9
C11—C16—C15	120.2 (2)	C40—C41—C36	120.4 (3)
C11—C16—H16	119.9	C40—C41—H41	119.8
C15—C16—H16	119.9	C36—C41—H41	119.8
O1—C17—C18	120.89 (18)	O2—C42—C43	122.00 (19)
O1—C17—C8	119.33 (18)	O2—C42—C33	119.04 (19)
C18—C17—C8	119.78 (17)	C43—C42—C33	118.92 (17)
C19—C18—C17	125.35 (19)	C44—C43—C42	121.33 (19)
C19—C18—H18	117.3	C44—C43—H43	119.3
C17—C18—H18	117.3	C42—C43—H43	119.3
C18—C19—C20	126.18 (19)	C43—C44—C45	127.8 (2)
C18—C19—H19	116.9	C43—C44—H44	116.1
C20—C19—H19	116.9	C45—C44—H44	116.1
C21—C20—C25	117.8 (2)	C50—C45—C46	118.0 (2)
C21—C20—C19	120.6 (2)	C50—C45—C44	123.49 (18)
C25—C20—C19	121.6 (2)	C46—C45—C44	118.5 (2)
C22—C21—C20	121.2 (2)	C47—C46—C45	121.2 (2)
C22—C21—H21	119.4	C47—C46—H46	119.4
C20—C21—H21	119.4	C45—C46—H46	119.4
C23—C22—C21	119.1 (2)	C48—C47—C46	119.3 (2)
C23—C22—H22	120.5	C48—C47—H47	120.4
C21—C22—H22	120.5	C46—C47—H47	120.4
C24—C23—C22	121.2 (2)	C47—C48—C49	121.2 (2)
C24—C23—Cl2	118.6 (2)	C47—C48—Cl4	119.60 (18)
C22—C23—Cl2	120.08 (19)	C49—C48—Cl4	119.2 (2)
C23—C24—C25	119.1 (2)	C50—C49—C48	119.0 (2)
C23—C24—H24	120.4	C50—C49—H49	120.5
C25—C24—H24	120.4	C48—C49—H49	120.5
C24—C25—C20	121.4 (2)	C49—C50—C45	121.3 (2)
C24—C25—H25	119.3	C49—C50—H50	119.4
C20—C25—H25	119.3	C45—C50—H50	119.4

C9—N1—C1—C2	−176.90 (17)	C34—N2—C26—C27	176.12 (18)
C9—N1—C1—C6	2.7 (3)	C34—N2—C26—C31	−3.2 (3)
N1—C1—C2—C3	−179.97 (18)	N2—C26—C27—C28	−179.62 (19)
C6—C1—C2—C3	0.4 (3)	C31—C26—C27—C28	−0.2 (3)
C1—C2—C3—C4	0.5 (3)	C26—C27—C28—C29	−0.9 (3)
C2—C3—C4—C5	−1.0 (3)	C27—C28—C29—C30	1.3 (3)
C2—C3—C4—Cl1	−179.51 (16)	C27—C28—C29—Cl3	−179.09 (17)
C3—C4—C5—C6	0.5 (3)	C28—C29—C30—C31	−0.7 (3)
Cl1—C4—C5—C6	179.04 (14)	Cl3—C29—C30—C31	179.77 (15)
C4—C5—C6—C1	0.4 (3)	C29—C30—C31—C26	−0.5 (3)
C4—C5—C6—C7	−177.66 (17)	C29—C30—C31—C32	177.63 (18)
N1—C1—C6—C5	179.54 (17)	N2—C26—C31—C30	−179.74 (17)
C2—C1—C6—C5	−0.9 (3)	C27—C26—C31—C30	0.9 (3)
N1—C1—C6—C7	−2.3 (3)	N2—C26—C31—C32	2.0 (3)
C2—C1—C6—C7	177.31 (16)	C27—C26—C31—C32	−177.30 (17)
C5—C6—C7—C8	177.51 (17)	C30—C31—C32—C33	−176.60 (17)
C1—C6—C7—C8	−0.6 (3)	C26—C31—C32—C33	1.5 (3)
C5—C6—C7—C11	−2.4 (3)	C30—C31—C32—C36	0.4 (3)
C1—C6—C7—C11	179.46 (16)	C26—C31—C32—C36	178.50 (17)
C6—C7—C8—C9	2.9 (3)	C31—C32—C33—C34	−3.8 (3)
C11—C7—C8—C9	−177.17 (17)	C36—C32—C33—C34	179.30 (17)
C6—C7—C8—C17	−173.98 (16)	C31—C32—C33—C42	174.06 (17)
C11—C7—C8—C17	6.0 (3)	C36—C32—C33—C42	−2.8 (3)
C1—N1—C9—C8	−0.2 (3)	C26—N2—C34—C33	0.8 (3)
C1—N1—C9—C10	−178.50 (17)	C26—N2—C34—C35	179.19 (17)
C7—C8—C9—N1	−2.6 (3)	C32—C33—C34—N2	2.7 (3)
C17—C8—C9—N1	174.28 (18)	C42—C33—C34—N2	−175.19 (18)
C7—C8—C9—C10	175.59 (19)	C32—C33—C34—C35	−175.55 (18)
C17—C8—C9—C10	−7.5 (3)	C42—C33—C34—C35	6.5 (3)
C8—C7—C11—C12	111.0 (2)	C33—C32—C36—C37	69.7 (3)
C6—C7—C11—C12	−69.0 (2)	C31—C32—C36—C37	−107.1 (2)
C8—C7—C11—C16	−69.5 (3)	C33—C32—C36—C41	−110.8 (2)
C6—C7—C11—C16	110.4 (2)	C31—C32—C36—C41	72.3 (3)
C16—C11—C12—C13	0.0 (3)	C41—C36—C37—C38	0.6 (4)
C7—C11—C12—C13	179.45 (19)	C32—C36—C37—C38	−179.9 (3)
C11—C12—C13—C14	−0.7 (4)	C36—C37—C38—C39	0.9 (5)
C12—C13—C14—C15	1.0 (4)	C37—C38—C39—C40	−1.2 (6)
C13—C14—C15—C16	−0.5 (4)	C38—C39—C40—C41	0.0 (6)
C12—C11—C16—C15	0.5 (3)	C39—C40—C41—C36	1.5 (5)
C7—C11—C16—C15	−178.98 (18)	C37—C36—C41—C40	−1.8 (4)
C14—C15—C16—C11	−0.2 (3)	C32—C36—C41—C40	178.7 (2)
C7—C8—C17—O1	91.2 (2)	C32—C33—C42—O2	−119.1 (3)
C9—C8—C17—O1	−85.7 (2)	C34—C33—C42—O2	58.8 (3)
C7—C8—C17—C18	−88.1 (2)	C32—C33—C42—C43	63.1 (3)
C9—C8—C17—C18	95.0 (2)	C34—C33—C42—C43	−119.0 (2)
O1—C17—C18—C19	−174.0 (2)	O2—C42—C43—C44	−5.8 (4)
C8—C17—C18—C19	5.3 (4)	C33—C42—C43—C44	171.9 (2)
C17—C18—C19—C20	176.6 (2)	C42—C43—C44—C45	−179.3 (2)
C18—C19—C20—C21	−159.6 (2)	C43—C44—C45—C50	8.2 (3)
C18—C19—C20—C25	19.1 (4)	C43—C44—C45—C46	−170.8 (2)
C25—C20—C21—C22	−3.5 (4)	C50—C45—C46—C47	−1.2 (3)
C19—C20—C21—C22	175.3 (2)	C44—C45—C46—C47	177.8 (2)
C20—C21—C22—C23	0.6 (4)	C45—C46—C47—C48	0.6 (3)
C21—C22—C23—C24	2.7 (4)	C46—C47—C48—C49	0.5 (3)
C21—C22—C23—Cl2	−175.03 (19)	C46—C47—C48—Cl4	−179.29 (17)
C22—C23—C24—C25	−2.9 (4)	C47—C48—C49—C50	−1.0 (3)
Cl2—C23—C24—C25	174.8 (2)	Cl4—C48—C49—C50	178.82 (17)
C23—C24—C25—C20	−0.2 (5)	C48—C49—C50—C45	0.3 (3)
C21—C20—C25—C24	3.3 (4)	C46—C45—C50—C49	0.8 (3)
C19—C20—C25—C24	−175.5 (3)	C44—C45—C50—C49	−178.2 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C20–C25 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C38—H38···Cg1ⁱ	0.93	2.93	3.458 (3)	117

Symmetry code: (i) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₅H₁₇Cl₂NO
M_r	418.30
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	11.1704 (3), 12.8497 (5), 16.0591 (6)
α, β, γ (°)	74.914 (3), 80.603 (3), 70.789 (3)
V (Å³)	2094.05 (13)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.91
Crystal size (mm)	0.30 × 0.30 × 0.10

Data collection
Diffractometer	Agilent Supernova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.574, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14958, 8252, 7088
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.158, 1.03
No. of reflections	8252
No. of parameters	525
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.41

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C20–C25 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C38—H38···Cg1ⁱ	0.93	2.93	3.458 (3)	117

Symmetry code: (i) −x+2, −y, −z+1.

Footnotes

‡Additional correspondence author, e-mail: kvpsvijayakumar@gmail.com.

Acknowledgements

VV is grateful to the DST, India, for funding through the Young Scientist Scheme (Fast Track Proposal). The authors are also grateful to the University of Malaya for support of the crystallographic facility.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Prasath, R., Sarveswari, S., Vijayakumar, V., Narasimhamurthy, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1110. Web of Science CSD CrossRef IUCr Journals Google Scholar
Reddy, P. B., Vijayakumar, V., Sarveswari, S., Narasimhamurthy, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o658–o659. Web of Science CSD CrossRef IUCr Journals Google Scholar
Roman, G. (2004). Acta Chim. Slov. 51, 537–544. CAS 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 67| Part 3| March 2011| Page o624

doi:10.1107/S1600536811004740

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

(2E)-1-(6-Chloro-2-methyl-4-phenyl­quinolin-3-yl)-3-(4-chloro­phen­yl)prop-2-en-1-one

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(2E)-1-(6-Chloro-2-methyl-4-phenylquinolin-3-yl)-3-(4-chlorophenyl)prop-2-en-1-one