(E)-3-(2,3-Di­chloro­phen­yl)-1-(4-fluoro­phen­yl)prop-2-en-1-one

Naveen, S.; Dileep Kumar, A.; Ajay Kumar, K.; Manjunath, H.R.; Lokanath, N.K.; Warad, I.

doi:10.1107/S2414314616018009

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 11| November 2016| x161800

https://doi.org/10.1107/S2414314616018009

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(E)-3-(2,3-Dichlorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one

S. Naveen,^a A. Dileep Kumar,^b K. Ajay Kumar,^b H. R. Manjunath,^c N. K. Lokanath ^d and Ismail Warad ^e ^*

^aInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India, ^bDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysuru 570 005, India, ^cDepartment of Physics, Acharya Institute of Technology, Visvesvaraya Technological University, Bangalore 560 107, India, ^dDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru 570 006, India, and ^eDepartment of Chemistry, Science College, An-Najah National University, PO Box 7, Nablus, West Bank, Palestinian Territories
^*Correspondence e-mail: khalil.i@najah.edu

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 8 November 2016; accepted 9 November 2016; online 15 November 2016)

In the title chalcone derivative, C₁₅H₉Cl₂FO, the dihedral angle between the aromatic rings is 19.13 (15)° and the double bond adopts an E conformation. In the crystal, molecules are connected by weak C—H⋯O hydrogen bonds, forming a chain propagating along the [001] direction.

Keywords: crystal structure; chalcone derivative; prop-2-en-1-one; hydrogen bonding.

CCDC reference: 1515842

Structure description

Chalcones are compounds that contain an α, β-unsaturated carbonyl function. The classical route for the synthesis of chalcones involves the Claisen–Schmidt condensation of an aromatic aldehyde and an aromatic ketone in the presence of aqueous alkaline bases (Jadav et al., 2015 ). As part of our studies in this area, we herein report the synthesis and crystal structure of the title compound (Fig. 1).

Figure 1
A view of the title compound, with displacement ellipsoids drawn at the 50% probability level.

The dihedral angle between the fluorophenyl and the dichlorophenyl rings is 19.35 (15)°. The trans conformation of the C7=C8 double bond in the central enone group is confirmed by the C7—C8=C9—C10 torsion angle value of −177.3 (2)°. The major twist in the molecule occurs about the C1—C7 bond, as indicated by the C2—C1—C7—C8 torsion angle of −18.5 (4)°.

In the crystal, the molecules are connected via weak C—H⋯O hydrogen bonds (Table 1), forming a C(7) chain propagating along the [001] direction (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.93	2.54	3.465 (4)	177
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 2
A view along the b axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1

Synthesis and crystallization

A mixture of 2,3-dichlorobenzaldehyde (0.05 mmol), 1-(4-fluorophenyl)ethanone (0.05 mmol) and sodium hydroxide (0.05 mmol) in 80% ethyl alcohol (25 ml) was stirred at room temperature for 3 h. The progress of the reaction was monitored by TLC. After the completion of the reaction, the mixture was poured in to ice-cold water and kept in the refrigerator for 18 h. The solid formed was filtered, and washed with cold acetic acid (5%). It was then recrystallized from dichloromethane solution (with 3–4 drops of acetonitrile added) to get the title compound in the form of green blocks, m.p. 105°C.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₉Cl₂FO
M_r	295.12
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	15.662 (2), 8.1130 (14), 10.9108 (18)
β (°)	106.288 (6)
V (Å³)	1330.8 (4)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	4.40
Crystal size (mm)	0.28 × 0.26 × 0.25

Data collection
Diffractometer	Bruker X8 Proteum
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )
T_min, T_max	0.372, 0.406
No. of measured, independent and observed [I > 2σ(I)] reflections	9531, 2163, 1881
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.584

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.210, 1.06
No. of reflections	2163
No. of parameters	173
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.52
Computer programs: APEX2 and SAINT (Bruker, 2013), SHELXS97 and SHELXL97 (Sheldrick, 2008 ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1515842

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616018009/hb4096sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616018009/hb4096Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616018009/hb4096Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).

(E)-3-(2,3-Dichlorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one top

Crystal data top

C₁₅H₉Cl₂FO	F(000) = 600
M_r = 295.12	D_x = 1.473 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 1881 reflections
a = 15.662 (2) Å	θ = 6.2–64.2°
b = 8.1130 (14) Å	µ = 4.40 mm⁻¹
c = 10.9108 (18) Å	T = 296 K
β = 106.288 (6)°	Block, green
V = 1330.8 (4) Å³	0.28 × 0.26 × 0.25 mm
Z = 4

Data collection top

Bruker X8 Proteum diffractometer	2163 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	1881 reflections with I > 2σ(I)
Helios multilayer optics monochromator	R_int = 0.053
Detector resolution: 18.4 pixels mm^-1	θ_max = 64.2°, θ_min = 6.2°
φ and ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −9→9
T_min = 0.372, T_max = 0.406	l = −11→12
9531 measured reflections

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)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.210	w = 1/[σ²(F_o²) + (0.1575P)² + 0.2475P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2163 reflections	Δρ_max = 0.51 e Å⁻³
173 parameters	Δρ_min = −0.52 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (3)

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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	−0.02367 (6)	0.65394 (16)	0.20294 (10)	0.0936 (5)
Cl2	0.12132 (5)	0.46410 (11)	0.11655 (7)	0.0673 (4)
F1	0.76924 (12)	0.0730 (3)	0.6363 (2)	0.0855 (8)
O1	0.40095 (14)	0.1717 (3)	0.2333 (2)	0.0638 (8)
C1	0.21279 (17)	0.4408 (3)	0.3681 (3)	0.0466 (9)
C2	0.2207 (2)	0.4739 (5)	0.4950 (3)	0.0633 (11)
C3	0.1557 (2)	0.5621 (5)	0.5317 (4)	0.0747 (14)
C4	0.0817 (2)	0.6185 (4)	0.4421 (4)	0.0676 (11)
C5	0.07215 (18)	0.5874 (4)	0.3154 (3)	0.0568 (10)
C6	0.13620 (16)	0.4998 (3)	0.2767 (3)	0.0471 (8)
C7	0.27948 (17)	0.3469 (3)	0.3273 (3)	0.0476 (9)
C8	0.36255 (17)	0.3194 (3)	0.3957 (3)	0.0496 (9)
C9	0.42414 (17)	0.2226 (3)	0.3428 (3)	0.0458 (8)
C10	0.51619 (16)	0.1877 (3)	0.4247 (3)	0.0433 (8)
C11	0.56881 (19)	0.0816 (4)	0.3774 (3)	0.0549 (10)
C12	0.6542 (2)	0.0431 (4)	0.4488 (4)	0.0628 (11)
C13	0.68611 (17)	0.1113 (4)	0.5673 (3)	0.0577 (10)
C14	0.6357 (2)	0.2145 (4)	0.6183 (3)	0.0646 (11)
C15	0.55032 (18)	0.2513 (4)	0.5467 (3)	0.0563 (10)
H2	0.27050	0.43640	0.55720	0.0760*
H3	0.16260	0.58280	0.61780	0.0890*
H4	0.03840	0.67750	0.46680	0.0810*
H7	0.26200	0.30220	0.24560	0.0570*
H8	0.38250	0.36150	0.47810	0.0590*
H11	0.54630	0.03580	0.29660	0.0660*
H12	0.68930	−0.02790	0.41670	0.0750*
H14	0.65870	0.25870	0.69960	0.0770*
H15	0.51510	0.31980	0.58070	0.0680*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0664 (6)	0.1289 (10)	0.0747 (8)	0.0475 (5)	0.0020 (5)	−0.0026 (5)
Cl2	0.0556 (6)	0.0992 (7)	0.0429 (6)	0.0174 (3)	0.0071 (4)	0.0060 (4)
F1	0.0460 (10)	0.1197 (17)	0.0812 (16)	0.0191 (10)	0.0020 (9)	0.0054 (12)
O1	0.0558 (12)	0.0856 (14)	0.0449 (13)	0.0090 (10)	0.0059 (10)	−0.0047 (11)
C1	0.0388 (13)	0.0550 (14)	0.0430 (17)	−0.0003 (10)	0.0066 (11)	0.0061 (11)
C2	0.0520 (16)	0.088 (2)	0.0457 (19)	0.0077 (14)	0.0069 (14)	0.0009 (15)
C3	0.067 (2)	0.107 (3)	0.049 (2)	0.0118 (18)	0.0146 (16)	−0.0114 (18)
C4	0.0566 (18)	0.080 (2)	0.067 (2)	0.0125 (15)	0.0187 (16)	−0.0123 (17)
C5	0.0472 (15)	0.0613 (15)	0.058 (2)	0.0083 (12)	0.0085 (13)	−0.0003 (14)
C6	0.0390 (13)	0.0522 (13)	0.0474 (17)	−0.0013 (11)	0.0076 (11)	0.0049 (12)
C7	0.0438 (14)	0.0530 (14)	0.0447 (17)	0.0030 (10)	0.0103 (11)	0.0074 (12)
C8	0.0431 (14)	0.0542 (15)	0.0484 (17)	0.0028 (11)	0.0080 (11)	0.0015 (12)
C9	0.0435 (13)	0.0475 (13)	0.0440 (17)	0.0008 (10)	0.0085 (11)	0.0049 (11)
C10	0.0406 (13)	0.0456 (12)	0.0431 (16)	0.0005 (10)	0.0106 (11)	0.0066 (11)
C11	0.0546 (16)	0.0687 (17)	0.0415 (18)	0.0126 (13)	0.0135 (13)	0.0034 (13)
C12	0.0542 (16)	0.076 (2)	0.061 (2)	0.0201 (14)	0.0206 (15)	0.0078 (15)
C13	0.0384 (14)	0.0694 (17)	0.062 (2)	0.0054 (12)	0.0086 (13)	0.0101 (15)
C14	0.0502 (15)	0.077 (2)	0.058 (2)	0.0015 (14)	0.0010 (14)	−0.0128 (15)
C15	0.0449 (15)	0.0621 (16)	0.059 (2)	0.0049 (12)	0.0100 (13)	−0.0106 (14)

Geometric parameters (Å, º) top

Cl1—C5	1.737 (3)	C10—C15	1.387 (4)
Cl2—C6	1.721 (3)	C11—C12	1.382 (5)
F1—C13	1.345 (4)	C12—C13	1.366 (5)
O1—C9	1.219 (4)	C13—C14	1.371 (4)
C1—C2	1.381 (4)	C14—C15	1.379 (4)
C1—C6	1.411 (4)	C2—H2	0.9300
C1—C7	1.460 (4)	C3—H3	0.9300
C2—C3	1.392 (5)	C4—H4	0.9300
C3—C4	1.369 (5)	C7—H7	0.9300
C4—C5	1.372 (5)	C8—H8	0.9300
C5—C6	1.388 (4)	C11—H11	0.9300
C7—C8	1.325 (4)	C12—H12	0.9300
C8—C9	1.481 (4)	C14—H14	0.9300
C9—C10	1.495 (4)	C15—H15	0.9300
C10—C11	1.388 (4)

C2—C1—C6	117.5 (3)	F1—C13—C14	119.4 (3)
C2—C1—C7	122.4 (3)	C12—C13—C14	122.2 (3)
C6—C1—C7	120.1 (3)	C13—C14—C15	118.7 (3)
C1—C2—C3	121.4 (3)	C10—C15—C14	121.0 (3)
C2—C3—C4	120.5 (4)	C1—C2—H2	119.00
C3—C4—C5	119.3 (3)	C3—C2—H2	119.00
Cl1—C5—C4	118.9 (2)	C2—C3—H3	120.00
Cl1—C5—C6	119.9 (2)	C4—C3—H3	120.00
C4—C5—C6	121.1 (3)	C3—C4—H4	120.00
Cl2—C6—C1	120.4 (2)	C5—C4—H4	120.00
Cl2—C6—C5	119.4 (2)	C1—C7—H7	117.00
C1—C6—C5	120.2 (3)	C8—C7—H7	117.00
C1—C7—C8	126.2 (3)	C7—C8—H8	120.00
C7—C8—C9	120.9 (3)	C9—C8—H8	120.00
O1—C9—C8	120.9 (3)	C10—C11—H11	120.00
O1—C9—C10	119.6 (3)	C12—C11—H11	120.00
C8—C9—C10	119.5 (3)	C11—C12—H12	121.00
C9—C10—C11	118.0 (3)	C13—C12—H12	121.00
C9—C10—C15	123.4 (2)	C13—C14—H14	121.00
C11—C10—C15	118.6 (3)	C15—C14—H14	121.00
C10—C11—C12	120.8 (3)	C10—C15—H15	120.00
C11—C12—C13	118.8 (3)	C14—C15—H15	120.00
F1—C13—C12	118.4 (3)

C6—C1—C2—C3	0.0 (5)	C7—C8—C9—O1	3.0 (4)
C7—C1—C2—C3	−179.2 (3)	C7—C8—C9—C10	−177.3 (2)
C2—C1—C6—Cl2	179.9 (2)	O1—C9—C10—C11	−7.4 (4)
C2—C1—C6—C5	−0.1 (4)	O1—C9—C10—C15	174.9 (3)
C7—C1—C6—Cl2	−0.8 (3)	C8—C9—C10—C11	173.0 (3)
C7—C1—C6—C5	179.2 (3)	C8—C9—C10—C15	−4.8 (4)
C2—C1—C7—C8	−18.5 (4)	C9—C10—C11—C12	−179.4 (3)
C6—C1—C7—C8	162.3 (3)	C15—C10—C11—C12	−1.6 (5)
C1—C2—C3—C4	0.1 (6)	C9—C10—C15—C14	179.8 (3)
C2—C3—C4—C5	−0.1 (5)	C11—C10—C15—C14	2.1 (4)
C3—C4—C5—Cl1	178.0 (3)	C10—C11—C12—C13	0.1 (5)
C3—C4—C5—C6	0.0 (5)	C11—C12—C13—F1	179.9 (3)
Cl1—C5—C6—Cl2	2.1 (3)	C11—C12—C13—C14	1.0 (5)
Cl1—C5—C6—C1	−177.9 (2)	F1—C13—C14—C15	−179.4 (3)
C4—C5—C6—Cl2	−179.9 (3)	C12—C13—C14—C15	−0.6 (5)
C4—C5—C6—C1	0.1 (4)	C13—C14—C15—C10	−1.0 (5)
C1—C7—C8—C9	−179.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.93	2.54	3.465 (4)	177

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

The authors are grateful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, India, for providing the single-crystal X-ray diffractometer facility.

References

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