(2E)-1-(2,4-Dichloro­phen­yl)-3-(quinolin-8-yl)prop-2-en-1-one

Sarojini, B.K.; Yathirajan, H.S.; Mayekar, A.N.; Narayana, B.; Bolte, M.

doi:10.1107/S1600536807032746

(2E)-1-(2,4-Dichlorophenyl)-3-(quinolin-8-yl)prop-2-en-1-one

B. K. Sarojini, H. S. Yathirajan, A. N. Mayekar, B. Narayana and M. Bolte

The geometric parameters of the molecule of the title compound, C₁₈H₁₁Cl₂NO, a chalcone derivative, are in the usual ranges. The central C=C double bond is trans configured. The dihedral angle between the two aromatic residues is 41.90 (8)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032746/lh2452sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032746/lh2452Isup2.hkl Contains datablock I

CCDC reference: 659077

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Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R factor = 0.057
wR factor = 0.154
Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.05

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Chalcones are one of the major classes of natural products have been recently subjects of great interest for their interesting pharmacological activities. Reviews on the bioactivities of varieties of chalcones are described. Recently, it has been noted that, among many organic compounds reported for their second harmonic generation, chalcone derivatives are known for their excellent blue light transmittance and good crystallizability. In continuation of our work on chalcones, the present paper reports the crystal structure of a newly synthesized chalcone. Geometric parameters of the title compound are in the usual ranges. The central C=C double bond is trans configured. The dihedral angle between the two aromatic residues is 41.90 (8)°. The C=C double bond is almost coplanar with the quinolyl residue [C2—C3—C21—C22 10.7 (4)°], but the two atoms of the carbonyl moiety are significantly twisted out of the plane of the dichlorophenyl substituent [O1—C1—C11—C12 - 53.3 (3)°]

Related literature top

For related structures, see: 3-(6-methoxy-2-naphthyl)-1-(2-naphthyl)prop-2-en-1-one (Yathirajan, Sarojini, Bindya et al., 2006); 3-(6-methoxy-2-naphthyl)-1-(2-thienyl)prop-2-en-1-one (Yathirajan, Narayana et al., 2006), 1-(2,4-dichloro-5-fluorophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one (Yathirajan, Sarojini, Narayana et al., 2006), (2E)-3-(6-methoxy-2-naphthyl)-1-phenylprop-2-en-1-one (Yathirajan, Mayekar, Sarojini et al., 2007), (2E)-1-(2,4-dichlorophenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one (Yathirajan, Mayekar, Narayana et al., 2007) and (E)-3-(2-ethoxyquinolin-3-yl)-1-(2-hydroxy-6-methylphenyl)prop-2-en-1-one (Bouraiou et al., 2007).

For related background, see: Dhar (1981); Dimmock et al. (1999); Fichou et al. (1988); Go et al. (2005); Goto et al. (1991).

Experimental top

To a thoroughly stirred solution of 2,4-dichloroacetophenone (1.89 g, 0.01 mol) and quinoline-8-carbaldehyde (1.57 g, 0.01 mol) in 25 ml me thanol, 5 ml of 40% KOH solution was added. The solution was stirred overnight and filtered. The product was crystallized from (1:1) acetone/toluene mixture (m.p.: 361–371 K). Analysis for C₁₈H₁₁Cl₂NO: Found (Calculated): C: 65.79 (65.87); H: 3.32 (3.38); N: 4.23 (4.27).

Structure description top

For related background, see: Dhar (1981); Dimmock et al. (1999); Fichou et al. (1988); Go et al. (2005); Goto et al. (1991).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level.

(2E)-1-(2,4-Dichlorophenyl)-3-quinolin-8-ylprop-2-en-1-one top

Crystal data top

C₁₈H₁₁Cl₂NO	F(000) = 672
M_r = 328.18	D_x = 1.454 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10809 reflections
a = 11.9121 (16) Å	θ = 3.6–25.7°
b = 10.7112 (10) Å	µ = 0.43 mm⁻¹
c = 12.7824 (15) Å	T = 173 K
β = 113.181 (9)°	Block, light yellow
V = 1499.3 (3) Å³	0.35 × 0.35 × 0.33 mm
Z = 4

Data collection top

Stoe IPDS II two-circle diffractometer	2808 independent reflections
Radiation source: fine-focus sealed tube	2328 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
ω scans	θ_max = 25.6°, θ_min = 3.6°
Absorption correction: multi-scan [MULABS (Spek, 2003; Blessing, 1995)]	h = −14→13
T_min = 0.863, T_max = 0.870	k = −12→13
12134 measured reflections	l = −15→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.154	w = 1/[σ²(F_o²) + (0.0986P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2808 reflections	Δρ_max = 0.55 e Å⁻³
200 parameters	Δρ_min = −0.50 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.027 (4)

Crystal data top

C₁₈H₁₁Cl₂NO	V = 1499.3 (3) Å³
M_r = 328.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.9121 (16) Å	µ = 0.43 mm⁻¹
b = 10.7112 (10) Å	T = 173 K
c = 12.7824 (15) Å	0.35 × 0.35 × 0.33 mm
β = 113.181 (9)°

Data collection top

Stoe IPDS II two-circle diffractometer	2808 independent reflections
Absorption correction: multi-scan [MULABS (Spek, 2003; Blessing, 1995)]	2328 reflections with I > 2σ(I)
T_min = 0.863, T_max = 0.870	R_int = 0.062
12134 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.03	Δρ_max = 0.55 e Å⁻³
2808 reflections	Δρ_min = −0.50 e Å⁻³
200 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
N1	0.67231 (18)	0.19606 (18)	0.46299 (17)	0.0292 (5)
O1	0.42301 (17)	0.13077 (16)	0.68460 (17)	0.0405 (5)
Cl1	0.14246 (5)	0.16535 (6)	0.57220 (5)	0.0364 (2)
Cl2	0.05375 (5)	0.50927 (6)	0.83447 (5)	0.0379 (3)
C1	0.4147 (2)	0.2440 (2)	0.6895 (2)	0.0286 (5)
C2	0.4905 (2)	0.3314 (2)	0.6565 (2)	0.0294 (5)
H2	0.4889	0.4178	0.6728	0.035*
C3	0.5614 (2)	0.2921 (2)	0.60420 (19)	0.0284 (5)
H3	0.5581	0.2057	0.5864	0.034*
C11	0.3234 (2)	0.3035 (2)	0.7296 (2)	0.0275 (5)
C12	0.1999 (2)	0.2740 (2)	0.68172 (19)	0.0277 (5)
C13	0.1160 (2)	0.3352 (2)	0.7146 (2)	0.0297 (6)
H13	0.0316	0.3152	0.6805	0.036*
C14	0.1587 (2)	0.4260 (2)	0.7982 (2)	0.0294 (5)
C15	0.2815 (2)	0.4551 (3)	0.8504 (2)	0.0348 (6)
H15	0.3095	0.5154	0.9096	0.042*
C16	0.3627 (2)	0.3944 (2)	0.8143 (2)	0.0337 (6)
H16	0.4469	0.4152	0.8482	0.040*
C21	0.6436 (2)	0.3695 (2)	0.57184 (19)	0.0272 (5)
C22	0.6716 (2)	0.4906 (2)	0.6084 (2)	0.0329 (6)
H22	0.6328	0.5274	0.6530	0.039*
C23	0.7559 (2)	0.5617 (2)	0.5819 (2)	0.0348 (6)
H23	0.7729	0.6453	0.6083	0.042*
C24	0.8138 (2)	0.5113 (2)	0.5181 (2)	0.0335 (6)
H24	0.8722	0.5595	0.5022	0.040*
C25	0.7873 (2)	0.3886 (2)	0.47589 (19)	0.0275 (5)
C26	0.7016 (2)	0.3163 (2)	0.50200 (18)	0.0248 (5)
C27	0.8423 (2)	0.3326 (2)	0.4070 (2)	0.0339 (6)
H27	0.8989	0.3782	0.3865	0.041*
C28	0.8130 (2)	0.2129 (3)	0.3707 (2)	0.0362 (6)
H28	0.8502	0.1733	0.3260	0.043*
C29	0.7268 (2)	0.1488 (2)	0.4003 (2)	0.0334 (6)
H29	0.7066	0.0658	0.3733	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0296 (11)	0.0304 (10)	0.0347 (10)	0.0011 (8)	0.0204 (8)	−0.0002 (8)
O1	0.0429 (11)	0.0303 (10)	0.0648 (13)	−0.0002 (8)	0.0389 (10)	−0.0012 (8)
Cl1	0.0338 (4)	0.0379 (4)	0.0442 (4)	−0.0070 (2)	0.0225 (3)	−0.0095 (3)
Cl2	0.0354 (4)	0.0447 (4)	0.0453 (4)	0.0112 (3)	0.0285 (3)	0.0025 (3)
C1	0.0253 (12)	0.0318 (13)	0.0365 (12)	−0.0014 (10)	0.0204 (10)	−0.0014 (10)
C2	0.0284 (12)	0.0301 (13)	0.0377 (13)	−0.0005 (9)	0.0217 (10)	−0.0018 (9)
C3	0.0287 (12)	0.0293 (12)	0.0336 (12)	−0.0022 (10)	0.0193 (10)	0.0008 (10)
C11	0.0287 (12)	0.0289 (12)	0.0334 (12)	−0.0010 (9)	0.0215 (10)	0.0020 (9)
C12	0.0297 (12)	0.0297 (12)	0.0321 (12)	0.0005 (10)	0.0212 (10)	0.0024 (10)
C13	0.0241 (12)	0.0366 (14)	0.0347 (12)	−0.0004 (9)	0.0184 (10)	0.0044 (10)
C14	0.0297 (12)	0.0330 (13)	0.0358 (12)	0.0067 (10)	0.0239 (10)	0.0052 (10)
C15	0.0349 (13)	0.0382 (14)	0.0383 (13)	−0.0011 (11)	0.0219 (11)	−0.0058 (11)
C16	0.0271 (12)	0.0411 (15)	0.0421 (14)	−0.0036 (10)	0.0234 (11)	−0.0049 (11)
C21	0.0258 (12)	0.0321 (13)	0.0292 (12)	−0.0004 (9)	0.0168 (10)	0.0023 (9)
C22	0.0355 (13)	0.0352 (14)	0.0366 (13)	−0.0014 (10)	0.0235 (11)	−0.0024 (10)
C23	0.0379 (13)	0.0321 (13)	0.0374 (13)	−0.0070 (11)	0.0179 (11)	−0.0021 (10)
C24	0.0307 (13)	0.0384 (14)	0.0341 (12)	−0.0080 (10)	0.0159 (10)	0.0068 (10)
C25	0.0222 (11)	0.0346 (13)	0.0293 (11)	−0.0004 (9)	0.0140 (9)	0.0047 (9)
C26	0.0219 (11)	0.0292 (12)	0.0277 (11)	0.0012 (9)	0.0144 (9)	0.0043 (9)
C27	0.0274 (12)	0.0475 (16)	0.0349 (13)	−0.0001 (10)	0.0210 (10)	0.0053 (11)
C28	0.0341 (14)	0.0466 (16)	0.0374 (13)	0.0051 (11)	0.0244 (11)	0.0016 (11)
C29	0.0377 (14)	0.0333 (13)	0.0365 (13)	0.0045 (10)	0.0224 (11)	−0.0007 (10)

Geometric parameters (Å, º) top

N1—C29	1.315 (3)	C15—H15	0.9500
N1—C26	1.375 (3)	C16—H16	0.9500
O1—C1	1.221 (3)	C21—C22	1.375 (4)
Cl1—C12	1.740 (2)	C21—C26	1.444 (3)
Cl2—C14	1.741 (2)	C22—C23	1.404 (3)
C1—C2	1.472 (3)	C22—H22	0.9500
C1—C11	1.515 (3)	C23—C24	1.368 (4)
C2—C3	1.335 (3)	C23—H23	0.9500
C2—H2	0.9500	C24—C25	1.409 (3)
C3—C21	1.462 (3)	C24—H24	0.9500
C3—H3	0.9500	C25—C27	1.420 (3)
C11—C12	1.389 (3)	C25—C26	1.423 (3)
C11—C16	1.393 (4)	C27—C28	1.361 (4)
C12—C13	1.391 (3)	C27—H27	0.9500
C13—C14	1.385 (3)	C28—C29	1.405 (4)
C13—H13	0.9500	C28—H28	0.9500
C14—C15	1.383 (4)	C29—H29	0.9500
C15—C16	1.386 (4)

C29—N1—C26	117.8 (2)	C22—C21—C26	118.1 (2)
O1—C1—C2	123.1 (2)	C22—C21—C3	122.7 (2)
O1—C1—C11	121.2 (2)	C26—C21—C3	119.2 (2)
C2—C1—C11	115.6 (2)	C21—C22—C23	122.1 (2)
C3—C2—C1	121.5 (2)	C21—C22—H22	119.0
C3—C2—H2	119.3	C23—C22—H22	119.0
C1—C2—H2	119.3	C24—C23—C22	120.4 (2)
C2—C3—C21	126.0 (2)	C24—C23—H23	119.8
C2—C3—H3	117.0	C22—C23—H23	119.8
C21—C3—H3	117.0	C23—C24—C25	120.5 (2)
C12—C11—C16	118.4 (2)	C23—C24—H24	119.8
C12—C11—C1	122.2 (2)	C25—C24—H24	119.8
C16—C11—C1	119.4 (2)	C24—C25—C27	122.9 (2)
C11—C12—C13	121.4 (2)	C24—C25—C26	119.4 (2)
C11—C12—Cl1	121.32 (18)	C27—C25—C26	117.7 (2)
C13—C12—Cl1	117.16 (18)	N1—C26—C25	121.8 (2)
C14—C13—C12	118.4 (2)	N1—C26—C21	118.7 (2)
C14—C13—H13	120.8	C25—C26—C21	119.5 (2)
C12—C13—H13	120.8	C28—C27—C25	119.3 (2)
C15—C14—C13	121.8 (2)	C28—C27—H27	120.3
C15—C14—Cl2	119.36 (19)	C25—C27—H27	120.3
C13—C14—Cl2	118.79 (18)	C27—C28—C29	119.0 (2)
C14—C15—C16	118.6 (2)	C27—C28—H28	120.5
C14—C15—H15	120.7	C29—C28—H28	120.5
C16—C15—H15	120.7	N1—C29—C28	124.4 (2)
C15—C16—C11	121.4 (2)	N1—C29—H29	117.8
C15—C16—H16	119.3	C28—C29—H29	117.8
C11—C16—H16	119.3

O1—C1—C2—C3	9.5 (4)	C26—C21—C22—C23	−1.3 (4)
C11—C1—C2—C3	−170.0 (2)	C3—C21—C22—C23	176.4 (2)
C1—C2—C3—C21	−177.4 (2)	C21—C22—C23—C24	−0.3 (4)
O1—C1—C11—C12	−53.3 (3)	C22—C23—C24—C25	1.6 (4)
C2—C1—C11—C12	126.2 (2)	C23—C24—C25—C27	178.4 (2)
O1—C1—C11—C16	129.1 (3)	C23—C24—C25—C26	−1.3 (3)
C2—C1—C11—C16	−51.4 (3)	C29—N1—C26—C25	0.2 (3)
C16—C11—C12—C13	1.7 (3)	C29—N1—C26—C21	−179.4 (2)
C1—C11—C12—C13	−175.9 (2)	C24—C25—C26—N1	180.0 (2)
C16—C11—C12—Cl1	177.84 (18)	C27—C25—C26—N1	0.3 (3)
C1—C11—C12—Cl1	0.2 (3)	C24—C25—C26—C21	−0.4 (3)
C11—C12—C13—C14	−1.0 (3)	C27—C25—C26—C21	180.0 (2)
Cl1—C12—C13—C14	−177.24 (18)	C22—C21—C26—N1	−178.7 (2)
C12—C13—C14—C15	−1.2 (3)	C3—C21—C26—N1	3.5 (3)
C12—C13—C14—Cl2	176.53 (18)	C22—C21—C26—C25	1.6 (3)
C13—C14—C15—C16	2.5 (4)	C3—C21—C26—C25	−176.2 (2)
Cl2—C14—C15—C16	−175.2 (2)	C24—C25—C27—C28	179.2 (2)
C14—C15—C16—C11	−1.7 (4)	C26—C25—C27—C28	−1.1 (4)
C12—C11—C16—C15	−0.4 (4)	C25—C27—C28—C29	1.4 (4)
C1—C11—C16—C15	177.3 (2)	C26—N1—C29—C28	0.1 (4)
C2—C3—C21—C22	10.7 (4)	C27—C28—C29—N1	−0.9 (4)
C2—C3—C21—C26	−171.6 (2)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₁Cl₂NO
M_r	328.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	11.9121 (16), 10.7112 (10), 12.7824 (15)
β (°)	113.181 (9)
V (Å³)	1499.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.35 × 0.35 × 0.33

Data collection
Diffractometer	Stoe IPDS II two-circle
Absorption correction	Multi-scan [MULABS (Spek, 2003; Blessing, 1995)]
T_min, T_max	0.863, 0.870
No. of measured, independent and observed [I > 2σ(I)] reflections	12134, 2808, 2328
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.154, 1.03
No. of reflections	2808
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.50

Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.

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(2E)-1-(2,4-Dichloro­phen­yl)-3-(quinolin-8-yl)prop-2-en-1-one

Supporting information

Key indicators

checkCIF/PLATON results

(2E)-1-(2,4-Dichlorophenyl)-3-(quinolin-8-yl)prop-2-en-1-one