(E)-3-(2,3-Di­chloro­phen­yl)-1-phenyl­prop-2-en-1-one

Naveen, S.; Dileep Kumar, A.; Lokeshwari, D.M.; Ajay Kumar, K.; Lokanath, N.K.; Warad, I.

doi:10.1107/S2414314617001262

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170126

https://doi.org/10.1107/S2414314617001262

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(E)-3-(2,3-Dichlorophenyl)-1-phenylprop-2-en-1-one

S. Naveen,^a A. Dileep Kumar,^b D. M. Lokeshwari,^b K. Ajay Kumar,^b N. K. Lokanath ^c ^* and Ismail Warad ^d ^*

^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 Studies in Physics, University of Mysore, Manasagangotri, Mysuru 570 006, India, and ^dDepartment of Chemistry, Science College, An-Najah National University, PO Box 7, Nablus, West Bank, Palestinian Territories
^*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in, khalil.i@najah.edu

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 24 January 2017; accepted 25 January 2017; online 3 February 2017)

In the title compound, C₁₅H₁₀Cl₂O, the dihedral angle between the aromatic rings is 5.59 (15)° and the C—C=C—C torsion angle is 177.5 (3)°. In the crystal, molecules are linked via pairs of C—H⋯O hydrogen bonds, forming inversion dimers with R₂²(10) ring motifs.

Keywords: crystal structure; chalcone; weak hydrogen bonds.

CCDC reference: 1529536

Structure description

As part of our ongoing studies of chalcone derivatives (Tejkiran et al., 2016 ; Kumara et al., 2017 ), we now report herein on the synthesis and crystal structure of the title compound.

The structure of the molecule is shown in Fig. 1. The molecule is nearly planar, with a dihedral angle of 5.59 (15)° between the aromatic rings that are bridged by the enone unit. This value is less than the value of 19.13 (15)° reported earlier between the aromatic rings in the related chalcone derivative (E)-3-(2,3-dichlorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one (Naveen et al., 2016 ). The trans conformation about the C7=C8 double bond in the central enone group is confirmed by the C2—C7=C8—C9 torsion angle of 177.5 (3)°. The carbonyl group at atom C9 lies almost in the plane of the olefinic double bond and phenyl ring as indicated by the O1—C9—C10—C11 and O1—C9—C8—C7 torsion angles of 2.9 (5) and 11.1 (5)°, respectively. The double-bond length in the propene unit [C7=C8 = 1.336 (4)°] is significantly longer than the value reported earlier for (2E)-1-(5-chlorothiophen-2-yl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one (Rodríguez-Lugo et al., 2015 ).

Figure 1
The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.

In the crystal, molecules are linked via pairs of weak C—H⋯O hydrogen bonds, forming inversion dimers with $[R_{2}^{2}]$ (10) ring motifs (Table 1, Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1ⁱ	0.93	2.48	3.360 (4)	159
Symmetry code: (i) -x+1, -y, -z.

Figure 2
C—H⋯O hydrogen bonds forming inversion dimers with $[R_{2}^{2}]$ (10) ring motifs.

Synthesis and crystallization

A mixture of 2,3-dichlorobenzaldehyde (0.05 mmol), acetophenone (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 into ice-cold water and kept in the refrigerator for 18 h. The solid formed was filtered, and washed with cold acetic acid (5%). The single crystals were obtained by recrystallization from a solution of the title compound in dichloromethane and 3–4 drops of acetonitrile (m.p. 391–392 K).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₀Cl₂O
M_r	277.13
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.7594 (19), 11.3610 (16), 8.0912 (11)
β (°)	97.139 (9)
V (Å³)	1255.0 (3)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	4.51
Crystal size (mm)	0.28 × 0.27 × 0.25

Data collection
Diffractometer	Bruker X8 Proteum
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )
T_min, T_max	0.365, 0.399
No. of measured, independent and observed [I > 2σ(I)] reflections	6357, 2010, 1748
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.584

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.193, 1.06
No. of reflections	2010
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.62
Computer programs: APEX2 and SAINT (Bruker, 2013), SHELXS97 and SHELXL97 (Sheldrick, 2008 ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1529536

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617001262/xu4023sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617001262/xu4023Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617001262/xu4023Isup3.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-phenylprop-2-en-1-one top

Crystal data top

C₁₅H₁₀Cl₂O	F(000) = 568
M_r = 277.13	D_x = 1.467 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 1748 reflections
a = 13.7594 (19) Å	θ = 6.5–64.3°
b = 11.3610 (16) Å	µ = 4.51 mm⁻¹
c = 8.0912 (11) Å	T = 296 K
β = 97.139 (9)°	Rectangle, yellow
V = 1255.0 (3) Å³	0.28 × 0.27 × 0.25 mm
Z = 4

Data collection top

Bruker X8 Proteum diffractometer	2010 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	1748 reflections with I > 2σ(I)
Helios multilayer optics monochromator	R_int = 0.056
Detector resolution: 18.4 pixels mm^-1	θ_max = 64.3°, θ_min = 6.5°
φ and ω scans	h = −15→16
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −12→12
T_min = 0.365, T_max = 0.399	l = −9→9
6357 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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.193	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.1509P)² + 0.1324P] where P = (F_o² + 2F_c²)/3
2010 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.62 e Å⁻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	1.04081 (6)	0.24127 (8)	0.72918 (10)	0.0411 (3)
Cl2	0.87488 (6)	0.09212 (6)	0.52852 (9)	0.0337 (3)
O1	0.5691 (2)	0.09538 (18)	0.1522 (3)	0.0397 (8)
C1	0.8669 (2)	0.2440 (3)	0.5286 (4)	0.0276 (9)
C2	0.7861 (2)	0.3004 (3)	0.4371 (4)	0.0270 (9)
C3	0.7826 (2)	0.4231 (3)	0.4453 (4)	0.0289 (9)
C4	0.8556 (2)	0.4871 (3)	0.5380 (4)	0.0338 (10)
C5	0.9341 (2)	0.4310 (3)	0.6275 (4)	0.0340 (10)
C6	0.9394 (2)	0.3097 (3)	0.6213 (4)	0.0309 (10)
C7	0.7101 (2)	0.2341 (3)	0.3350 (4)	0.0280 (9)
C8	0.6215 (2)	0.2747 (3)	0.2755 (4)	0.0276 (9)
C9	0.5519 (2)	0.2003 (3)	0.1673 (4)	0.0276 (9)
C10	0.4623 (2)	0.2540 (2)	0.0750 (4)	0.0258 (9)
C11	0.3971 (2)	0.1808 (3)	−0.0221 (4)	0.0291 (9)
C12	0.3129 (2)	0.2265 (3)	−0.1114 (4)	0.0336 (10)
C13	0.2927 (2)	0.3456 (3)	−0.1034 (4)	0.0353 (10)
C14	0.3576 (3)	0.4189 (3)	−0.0083 (4)	0.0347 (10)
C15	0.4414 (2)	0.3744 (3)	0.0803 (4)	0.0313 (9)
H3	0.73000	0.46270	0.38700	0.0350*
H4	0.85170	0.56880	0.54000	0.0410*
H5	0.98270	0.47410	0.69100	0.0410*
H7	0.72470	0.15680	0.30900	0.0340*
H8	0.60340	0.35050	0.30250	0.0330*
H11	0.41010	0.10070	−0.02710	0.0350*
H12	0.27010	0.17710	−0.17680	0.0400*
H13	0.23580	0.37620	−0.16160	0.0420*
H14	0.34440	0.49910	−0.00410	0.0420*
H15	0.48440	0.42460	0.14390	0.0380*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0359 (6)	0.0413 (6)	0.0449 (6)	−0.0008 (3)	0.0001 (4)	0.0089 (4)
Cl2	0.0406 (6)	0.0214 (5)	0.0391 (5)	0.0029 (3)	0.0055 (4)	0.0040 (3)
O1	0.0523 (15)	0.0163 (13)	0.0480 (14)	0.0031 (9)	−0.0036 (11)	−0.0023 (9)
C1	0.0343 (17)	0.0208 (16)	0.0299 (16)	0.0018 (12)	0.0128 (14)	0.0046 (11)
C2	0.0337 (16)	0.0233 (15)	0.0257 (15)	0.0004 (13)	0.0102 (12)	0.0003 (12)
C3	0.0344 (17)	0.0210 (15)	0.0317 (16)	0.0005 (12)	0.0054 (13)	0.0038 (12)
C4	0.0436 (18)	0.0219 (16)	0.0375 (17)	−0.0045 (13)	0.0120 (14)	−0.0009 (13)
C5	0.0366 (18)	0.0348 (17)	0.0323 (16)	−0.0081 (14)	0.0114 (14)	−0.0011 (14)
C6	0.0331 (17)	0.0298 (17)	0.0305 (16)	−0.0009 (13)	0.0068 (13)	0.0048 (13)
C7	0.0400 (19)	0.0196 (15)	0.0259 (15)	−0.0003 (12)	0.0099 (13)	0.0010 (12)
C8	0.0365 (17)	0.0167 (14)	0.0304 (16)	0.0012 (12)	0.0078 (13)	0.0003 (12)
C9	0.0391 (17)	0.0156 (16)	0.0293 (16)	−0.0002 (13)	0.0087 (13)	0.0016 (11)
C10	0.0314 (17)	0.0204 (15)	0.0269 (15)	−0.0004 (12)	0.0093 (12)	0.0013 (11)
C11	0.0375 (17)	0.0182 (15)	0.0338 (16)	−0.0021 (12)	0.0133 (14)	−0.0024 (12)
C12	0.0377 (18)	0.0292 (18)	0.0351 (17)	−0.0037 (13)	0.0091 (14)	−0.0017 (14)
C13	0.0346 (17)	0.0331 (18)	0.0387 (17)	0.0024 (14)	0.0068 (13)	0.0054 (14)
C14	0.0378 (18)	0.0208 (16)	0.0460 (19)	0.0014 (13)	0.0073 (15)	0.0009 (14)
C15	0.0357 (17)	0.0194 (15)	0.0398 (16)	−0.0010 (13)	0.0083 (14)	−0.0022 (13)

Geometric parameters (Å, º) top

Cl1—C6	1.735 (3)	C11—C12	1.388 (4)
Cl2—C1	1.729 (3)	C12—C13	1.385 (5)
O1—C9	1.224 (4)	C13—C14	1.383 (5)
C1—C2	1.411 (4)	C14—C15	1.376 (5)
C1—C6	1.389 (4)	C3—H3	0.9300
C2—C3	1.397 (5)	C4—H4	0.9300
C2—C7	1.459 (4)	C5—H5	0.9300
C3—C4	1.383 (4)	C7—H7	0.9300
C4—C5	1.379 (4)	C8—H8	0.9300
C5—C6	1.381 (5)	C11—H11	0.9300
C7—C8	1.336 (4)	C12—H12	0.9300
C8—C9	1.480 (4)	C13—H13	0.9300
C9—C10	1.490 (4)	C14—H14	0.9300
C10—C11	1.392 (4)	C15—H15	0.9300
C10—C15	1.400 (4)

Cl2—C1—C2	119.9 (2)	C13—C14—C15	120.7 (3)
Cl2—C1—C6	119.7 (2)	C10—C15—C14	120.3 (3)
C2—C1—C6	120.4 (3)	C2—C3—H3	119.00
C1—C2—C3	117.3 (3)	C4—C3—H3	119.00
C1—C2—C7	121.7 (3)	C3—C4—H4	120.00
C3—C2—C7	121.0 (3)	C5—C4—H4	120.00
C2—C3—C4	121.6 (3)	C4—C5—H5	121.00
C3—C4—C5	120.7 (3)	C6—C5—H5	121.00
C4—C5—C6	118.9 (3)	C2—C7—H7	117.00
Cl1—C6—C1	120.6 (3)	C8—C7—H7	117.00
Cl1—C6—C5	118.1 (2)	C7—C8—H8	120.00
C1—C6—C5	121.2 (3)	C9—C8—H8	120.00
C2—C7—C8	125.7 (3)	C10—C11—H11	120.00
C7—C8—C9	120.7 (3)	C12—C11—H11	120.00
O1—C9—C8	119.8 (3)	C11—C12—H12	120.00
O1—C9—C10	120.4 (3)	C13—C12—H12	120.00
C8—C9—C10	119.8 (3)	C12—C13—H13	120.00
C9—C10—C11	118.2 (2)	C14—C13—H13	120.00
C9—C10—C15	123.0 (3)	C13—C14—H14	120.00
C11—C10—C15	118.7 (3)	C15—C14—H14	120.00
C10—C11—C12	120.5 (3)	C10—C15—H15	120.00
C11—C12—C13	120.1 (3)	C14—C15—H15	120.00
C12—C13—C14	119.7 (3)

Cl2—C1—C2—C3	178.5 (2)	C2—C7—C8—C9	177.5 (3)
Cl2—C1—C2—C7	−2.8 (4)	C7—C8—C9—O1	11.1 (5)
C6—C1—C2—C3	−0.4 (4)	C7—C8—C9—C10	−167.8 (3)
C6—C1—C2—C7	178.3 (3)	O1—C9—C10—C11	2.9 (5)
Cl2—C1—C6—Cl1	3.0 (4)	O1—C9—C10—C15	−176.5 (3)
Cl2—C1—C6—C5	−178.4 (2)	C8—C9—C10—C11	−178.3 (3)
C2—C1—C6—Cl1	−178.1 (2)	C8—C9—C10—C15	2.4 (5)
C2—C1—C6—C5	0.5 (5)	C9—C10—C11—C12	−179.6 (3)
C1—C2—C3—C4	0.5 (5)	C15—C10—C11—C12	−0.2 (5)
C7—C2—C3—C4	−178.2 (3)	C9—C10—C15—C14	179.7 (3)
C1—C2—C7—C8	163.8 (3)	C11—C10—C15—C14	0.4 (5)
C3—C2—C7—C8	−17.5 (5)	C10—C11—C12—C13	−0.5 (5)
C2—C3—C4—C5	−0.8 (5)	C11—C12—C13—C14	1.1 (5)
C3—C4—C5—C6	0.9 (5)	C12—C13—C14—C15	−0.9 (5)
C4—C5—C6—Cl1	177.9 (2)	C13—C14—C15—C10	0.2 (5)
C4—C5—C6—C1	−0.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1ⁱ	0.93	2.48	3.360 (4)	159

Symmetry code: (i) −x+1, −y, −z.

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.

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