(E)-1-(Benzo[d][1,3]dioxol-5-yl)-3-(2,3-di­chloro­phen­yl)prop-2-en-1-one

Lokeshwari, D.M.; Pavithra, G.; Renuka, N.; Lokanath, N.K.; Naveen, S.; Ajay Kumar, K.

doi:10.1107/S2414314617001031

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 1| January 2017| x170103

https://doi.org/10.1107/S2414314617001031

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(E)-1-(Benzo[d][1,3]dioxol-5-yl)-3-(2,3-dichlorophenyl)prop-2-en-1-one

D. M. Lokeshwari,^a G. Pavithra,^a N. Renuka,^b N. K. Lokanath,^c S. Naveen ^d ^* and K. Ajay Kumar ^a ^*

^aDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysuru 570 005, India, ^bDepartment of Chemistry, GSSS Institute of Engineering and Technology for Women, Mysuru 570 016, India, ^cDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru 570 006, India, and ^dInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India
^*Correspondence e-mail: naveen@ioe.uni-mysore.ac.in, ajaykumar@ycm.uni-mysore.ac.in

Edited by J. Simpson, University of Otago, New Zealand (Received 19 January 2017; accepted 20 January 2017; online 27 January 2017)

In the title compound, C₁₆H₁₀Cl₂O₃, the olefinic double bond adopts an E conformation [C—C=C—C torsion angle = −172.9 (3)°]. The dihedral angle between the benzodioxole and dichlorobenzene rings is 5.57 (9)°. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯Cl hydrogen bonds, forming chains propagating along the c-axis direction.

Keywords: crystal structure; bis-chalcone; E configuration.

CCDC reference: 1528716

Structure description

Chalcones constitute the central cores for the construction of a wide range of bioactive compounds (Naveen et al., 2016 ). As part of our ongoing work on such molecules (Kumara et al., 2017 ), we report the synthesis and crystal structure of the title compound here.

The structure of the molecule is shown in Fig. 1. The molecule is nearly planar, with a dihedral angle of 5.57 (9)° between the benzodioxole and dichloro benzene rings that are bridged by the olefinic double bond. This value is comparable with the value of 6.99 (6)° reported earlier between the aromatic rings in the related chalcone derivative (E)-1-(1,3-benzodioxol-5-yl)-3-(2,4,5-trimethoxy-phenyl)prop-2-en-1-one. (Sunitha et al., 2017 ). The trans conformation about the C7=C8 double bond in the central enone group is confirmed by the C4—C7=C8—C9 torsion angle, −172.9 (3)°. The carbonyl group at C7 lies almost in the plane of the olefinic double bond and benzodioxole ring as indicated by the C3—C4—C7—O3 and O3—C7—C8—C9 torsion angles 6.2 (3)° and 7.6 (4)° respectively.

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

In the crystal, the molecules are linked via weak C—H⋯O and C—H⋯Cl hydrogen bonds, forming chains propagating along the c-axis direction (Table 1 and Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cl1	0.93	2.58	3.033 (3)	110
C9—H9⋯O3	0.93	2.48	2.809 (4)	101
C14—H14⋯O1ⁱ	0.93	2.59	3.194 (3)	123
Symmetry code: (i) $[x-1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 2
Packing of the molecules, viewed along the c axis, with hydrogen bonds shown as dashed lines.

Synthesis and crystallization

A mixture of 2,3-dichlorobenzaldehyde (5 mmol), 1-(benzo[d][1,3]dioxol-5-yl)ethanone (5 mmol) and sodium hydroxide (5 mmol) in methanol (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 a refrigerator for 18 h. The solid that formed was filtered, and washed with cold hydrochloric acid (5%). Pure white crystals were obtained by slow evaporation from a methanol solution (yield 88%, m.p. 401–402 K).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₀Cl₂O₃
M_r	321.14
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.1854 (7), 11.0820 (8), 12.2077 (9)
β (°)	99.068 (3)
V (Å³)	1360.72 (17)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	4.36
Crystal size (mm)	0.28 × 0.26 × 0.24

Data collection
Diffractometer	Bruker X8 Proteum
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )
T_min, T_max	0.375, 0.421
No. of measured, independent and observed [I > 2σ(I)] reflections	8712, 2232, 2086
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.586

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.158, 1.03
No. of reflections	2232
No. of parameters	190
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.38
Computer programs: APEX2 and SAINT (Bruker, 2013), SHELXS97 and SHELXL97 (Sheldrick, 2008 ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1528716

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617001031/sj4082sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617001031/sj4082Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617001031/sj4082Isup3.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)-1-(Benzo[d][1,3]dioxol-5-yl)-3-(2,3-dichlorophenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₀Cl₂O₃	F(000) = 656
M_r = 321.14	D_x = 1.568 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 2086 reflections
a = 10.1854 (7) Å	θ = 4.4–64.5°
b = 11.0820 (8) Å	µ = 4.36 mm⁻¹
c = 12.2077 (9) Å	T = 296 K
β = 99.068 (3)°	Rectangle, white
V = 1360.72 (17) Å³	0.28 × 0.26 × 0.24 mm
Z = 4

Data collection top

Bruker X8 Proteum diffractometer	2232 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2086 reflections with I > 2σ(I)
Helios multilayer optics monochromator	R_int = 0.048
Detector resolution: 18.4 pixels mm^-1	θ_max = 64.5°, θ_min = 4.4°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −10→12
T_min = 0.375, T_max = 0.421	l = −14→13
8712 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 atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.1218P)² + 0.554P] where P = (F_o² + 2F_c²)/3
2232 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.38 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	−0.13750 (6)	0.03536 (6)	0.24874 (5)	0.0316 (3)
Cl2	−0.37087 (6)	−0.00563 (6)	0.38206 (6)	0.0377 (3)
O1	0.76711 (18)	0.39765 (18)	0.31535 (15)	0.0353 (6)
O2	0.80348 (18)	0.45912 (17)	0.49834 (15)	0.0322 (6)
O3	0.3035 (2)	0.20086 (19)	0.24062 (16)	0.0393 (7)
C1	0.8544 (3)	0.4624 (2)	0.3945 (2)	0.0304 (8)
C2	0.6590 (2)	0.3683 (2)	0.3649 (2)	0.0260 (7)
C3	0.5445 (2)	0.3131 (2)	0.3184 (2)	0.0272 (8)
C4	0.4480 (2)	0.2919 (2)	0.3881 (2)	0.0261 (7)
C5	0.4743 (3)	0.3250 (2)	0.4999 (2)	0.0273 (7)
C6	0.5927 (2)	0.3814 (2)	0.5459 (2)	0.0282 (7)
C7	0.3208 (3)	0.2367 (2)	0.3373 (2)	0.0292 (8)
C8	0.2132 (3)	0.2262 (3)	0.4053 (2)	0.0353 (8)
C9	0.1024 (3)	0.1677 (2)	0.3710 (2)	0.0287 (8)
C10	−0.0084 (2)	0.1487 (2)	0.4320 (2)	0.0252 (7)
C11	−0.1248 (2)	0.0878 (2)	0.3834 (2)	0.0255 (7)
C12	−0.2286 (2)	0.0698 (2)	0.4426 (2)	0.0273 (8)
C13	−0.2211 (3)	0.1102 (2)	0.5504 (2)	0.0311 (8)
C14	−0.1074 (3)	0.1695 (2)	0.5994 (2)	0.0311 (8)
C15	−0.0023 (3)	0.1880 (2)	0.5422 (2)	0.0284 (8)
C16	0.6823 (2)	0.4034 (2)	0.4754 (2)	0.0256 (7)
H1	0.86110	0.54520	0.37040	0.0360*
H3	0.94230	0.42640	0.40360	0.0360*
H5	0.41090	0.30880	0.54500	0.0330*
H6	0.61000	0.40300	0.62040	0.0340*
H8	0.22450	0.26250	0.47490	0.0420*
H9	0.09340	0.13470	0.30020	0.0340*
H10	0.53010	0.29020	0.24420	0.0330*
H13	−0.29130	0.09770	0.58940	0.0370*
H14	−0.10160	0.19730	0.67180	0.0370*
H15	0.07360	0.22720	0.57720	0.0340*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0261 (4)	0.0429 (5)	0.0243 (4)	−0.0032 (2)	−0.0007 (3)	−0.0032 (2)
Cl2	0.0241 (4)	0.0427 (5)	0.0458 (5)	−0.0060 (3)	0.0038 (3)	−0.0033 (3)
O1	0.0295 (10)	0.0491 (11)	0.0295 (10)	−0.0069 (8)	0.0113 (8)	−0.0014 (8)
O2	0.0233 (10)	0.0450 (11)	0.0277 (10)	−0.0076 (8)	0.0026 (8)	0.0003 (8)
O3	0.0365 (11)	0.0494 (12)	0.0314 (11)	−0.0144 (9)	0.0039 (8)	−0.0068 (9)
C1	0.0240 (13)	0.0345 (14)	0.0344 (15)	−0.0024 (11)	0.0103 (11)	0.0075 (11)
C2	0.0224 (12)	0.0284 (13)	0.0274 (12)	0.0036 (10)	0.0045 (10)	0.0040 (10)
C3	0.0279 (13)	0.0290 (13)	0.0246 (13)	0.0002 (10)	0.0042 (10)	−0.0016 (10)
C4	0.0240 (13)	0.0234 (12)	0.0303 (13)	0.0023 (10)	0.0027 (10)	0.0005 (10)
C5	0.0231 (12)	0.0290 (13)	0.0307 (13)	0.0012 (10)	0.0069 (10)	0.0051 (10)
C6	0.0273 (13)	0.0342 (13)	0.0229 (12)	0.0005 (11)	0.0037 (10)	0.0023 (10)
C7	0.0282 (14)	0.0260 (12)	0.0334 (14)	−0.0007 (10)	0.0048 (11)	0.0015 (10)
C8	0.0293 (14)	0.0390 (15)	0.0387 (15)	−0.0037 (12)	0.0092 (12)	−0.0097 (12)
C9	0.0308 (14)	0.0293 (13)	0.0245 (12)	−0.0035 (11)	−0.0004 (11)	0.0002 (10)
C10	0.0258 (13)	0.0201 (12)	0.0286 (13)	0.0010 (10)	0.0013 (10)	0.0026 (10)
C11	0.0268 (13)	0.0233 (12)	0.0245 (12)	0.0034 (10)	−0.0015 (10)	0.0008 (10)
C12	0.0218 (13)	0.0216 (12)	0.0369 (14)	0.0021 (10)	−0.0005 (11)	0.0008 (10)
C13	0.0310 (14)	0.0275 (13)	0.0365 (14)	0.0056 (11)	0.0103 (11)	0.0025 (11)
C14	0.0392 (15)	0.0249 (13)	0.0302 (13)	−0.0001 (11)	0.0086 (11)	−0.0031 (10)
C15	0.0320 (14)	0.0237 (13)	0.0280 (13)	−0.0030 (10)	−0.0001 (10)	−0.0003 (10)
C16	0.0217 (12)	0.0251 (12)	0.0286 (13)	0.0015 (10)	−0.0002 (10)	0.0043 (10)

Geometric parameters (Å, º) top

Cl1—C11	1.729 (2)	C10—C11	1.411 (3)
Cl2—C12	1.734 (2)	C10—C15	1.406 (3)
O1—C1	1.403 (3)	C11—C12	1.386 (3)
O1—C2	1.376 (3)	C12—C13	1.381 (3)
O2—C1	1.444 (3)	C13—C14	1.383 (4)
O2—C16	1.369 (3)	C14—C15	1.383 (4)
O3—C7	1.231 (3)	C1—H1	0.9700
C2—C3	1.359 (3)	C1—H3	0.9700
C2—C16	1.388 (3)	C3—H10	0.9300
C3—C4	1.417 (3)	C5—H5	0.9300
C4—C5	1.398 (3)	C6—H6	0.9300
C4—C7	1.478 (4)	C8—H8	0.9300
C5—C6	1.395 (4)	C9—H9	0.9300
C6—C16	1.371 (3)	C13—H13	0.9300
C7—C8	1.480 (4)	C14—H14	0.9300
C8—C9	1.312 (4)	C15—H15	0.9300
C9—C10	1.462 (4)

C1—O1—C2	106.40 (19)	C13—C14—C15	121.0 (2)
C1—O2—C16	105.59 (19)	C10—C15—C14	121.1 (2)
O1—C1—O2	108.4 (2)	O2—C16—C2	109.62 (19)
O1—C2—C3	128.0 (2)	O2—C16—C6	128.3 (2)
O1—C2—C16	109.56 (19)	C2—C16—C6	122.1 (2)
C3—C2—C16	122.4 (2)	O1—C1—H1	110.00
C2—C3—C4	117.0 (2)	O1—C1—H3	110.00
C3—C4—C5	119.9 (2)	O2—C1—H1	110.00
C3—C4—C7	117.5 (2)	O2—C1—H3	110.00
C5—C4—C7	122.6 (2)	H1—C1—H3	108.00
C4—C5—C6	122.1 (2)	C2—C3—H10	122.00
C5—C6—C16	116.5 (2)	C4—C3—H10	121.00
O3—C7—C4	121.3 (3)	C4—C5—H5	119.00
O3—C7—C8	120.4 (3)	C6—C5—H5	119.00
C4—C7—C8	118.4 (2)	C5—C6—H6	122.00
C7—C8—C9	122.4 (2)	C16—C6—H6	122.00
C8—C9—C10	127.1 (2)	C7—C8—H8	119.00
C9—C10—C11	121.3 (2)	C9—C8—H8	119.00
C9—C10—C15	121.4 (2)	C8—C9—H9	116.00
C11—C10—C15	117.3 (2)	C10—C9—H9	116.00
Cl1—C11—C10	119.50 (17)	C12—C13—H13	121.00
Cl1—C11—C12	119.90 (17)	C14—C13—H13	121.00
C10—C11—C12	120.6 (2)	C13—C14—H14	120.00
Cl2—C12—C11	120.14 (18)	C15—C14—H14	120.00
Cl2—C12—C13	118.65 (19)	C10—C15—H15	120.00
C11—C12—C13	121.2 (2)	C14—C15—H15	119.00
C12—C13—C14	118.9 (2)

C2—O1—C1—O2	6.8 (2)	C5—C6—C16—O2	178.6 (2)
C1—O1—C2—C3	174.9 (2)	C5—C6—C16—C2	−2.0 (3)
C1—O1—C2—C16	−5.4 (3)	O3—C7—C8—C9	7.6 (4)
C16—O2—C1—O1	−5.7 (2)	C4—C7—C8—C9	−172.9 (3)
C1—O2—C16—C2	2.4 (2)	C7—C8—C9—C10	178.1 (2)
C1—O2—C16—C6	−178.1 (2)	C8—C9—C10—C11	177.4 (3)
O1—C2—C3—C4	179.5 (2)	C8—C9—C10—C15	−4.0 (4)
C16—C2—C3—C4	−0.2 (3)	C9—C10—C11—Cl1	−0.4 (3)
O1—C2—C16—O2	1.8 (3)	C9—C10—C11—C12	179.6 (2)
O1—C2—C16—C6	−177.7 (2)	C15—C10—C11—Cl1	−179.11 (17)
C3—C2—C16—O2	−178.5 (2)	C15—C10—C11—C12	0.9 (3)
C3—C2—C16—C6	2.0 (4)	C9—C10—C15—C14	−179.9 (2)
C2—C3—C4—C5	−1.5 (3)	C11—C10—C15—C14	−1.2 (3)
C2—C3—C4—C7	177.4 (2)	Cl1—C11—C12—Cl2	0.2 (3)
C3—C4—C5—C6	1.4 (3)	Cl1—C11—C12—C13	179.73 (18)
C7—C4—C5—C6	−177.4 (2)	C10—C11—C12—Cl2	−179.78 (17)
C3—C4—C7—O3	6.2 (3)	C10—C11—C12—C13	−0.3 (3)
C3—C4—C7—C8	−173.3 (2)	Cl2—C12—C13—C14	179.45 (18)
C5—C4—C7—O3	−175.0 (2)	C11—C12—C13—C14	−0.1 (3)
C5—C4—C7—C8	5.5 (3)	C12—C13—C14—C15	−0.3 (4)
C4—C5—C6—C16	0.3 (3)	C13—C14—C15—C10	0.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cl1	0.93	2.58	3.033 (3)	110
C9—H9···O3	0.93	2.48	2.809 (4)	101
C14—H14···O1ⁱ	0.93	2.59	3.194 (3)	123

Symmetry code: (i) x−1, −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.

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