(E)-1-(2,5-Dichloro-3-thien­yl)-3-(3,4-dimeth­oxy­phen­yl)prop-2-en-1-one

Harrison, W.T.A.; Chidan Kumar, C.S.; Yathirajan, H.S.; Mayekar, A.N.; Narayana, B.

doi:10.1107/S1600536810035142

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2479

doi:10.1107/S1600536810035142

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(E)-1-(2,5-Dichloro-3-thienyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one

William T. A. Harrison,^a ^* C. S. Chidan Kumar,^b H. S. Yathirajan,^b A. N. Mayekar ^b,^c and B. Narayana ^d

^aDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, ^cSeQuent Scientific Limited, New Mangalore 575 011, India, and ^dDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, India
^*Correspondence e-mail: w.harrison@abdn.ac.uk

(Received 6 August 2010; accepted 31 August 2010; online 4 September 2010)

In the title compound, C₁₅H₁₂Cl₂O₃S, the prop-2-en-1-one (enone) fragment is almost planar [C—C—C—O = 2.2 (4)°] and it subtends dihedral angles of 11.9 (2) and 11.0 (2)° with the thiophene and benzene rings, respectively. The dihedral angle between the aromatic rings is 3.47 (16)°. In the crystal, weak C—H⋯O and C—H⋯Cl interactions link the molecules, leading to R₂²(14), R₂²(24) and C(11) supramolecular motifs occurring within the three-dimensional network. Weak aromatic π–π stacking [centroid–centroid separations = 3.6823 (15) and 3.8722 (15) Å] may also help to consolidate the packing.

Related literature

For a related structure and background references, see: Jasinski et al. (2010 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₂Cl₂O₃S
M_r = 343.21
Monoclinic, P 2₁ /n
a = 8.9331 (2) Å
b = 8.9997 (2) Å
c = 18.8210 (5) Å
β = 100.181 (1)°
V = 1489.29 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.58 mm⁻¹
T = 120 K
0.24 × 0.12 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan [SADABS (Bruker, 2003 ) and Blessing (1995 )] T_min = 0.873, T_max = 0.944
22032 measured reflections
3424 independent reflections
2834 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.113
S = 1.10
3424 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3ⁱ	0.95	2.53	3.227 (3)	130
C12—H12⋯O1ⁱⁱ	0.95	2.55	3.441 (3)	157
C14—H14A⋯O3ⁱⁱⁱ	0.98	2.53	3.474 (3)	161
C15—H15B⋯Cl1^iv	0.98	2.82	3.647 (3)	142
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) -x, -y+1, -z+1.

Data collection: COLLECT (Nonius, 1998 ); cell refinement: COLLECT; data reduction: DENZO (Otwinowski & Minor, 1997 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035142/ng5014sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035142/ng5014Isup2.hkl

checkCIF report

Comment top

The title compound, (I), (Fig. 1), was prepared as part of our ongoing structural studies (Jasinski et al., 2010) of chalcone-like compounds, in which substituted aromatic ring systems are linked by a prop-2-en-1-one bridge.

The prop-2-en-1-one fragment in (I) is almost planar [C7—C8—C9—O3 = 2.2 (4)°] and it subtends dihedral angles of 11.9 (2) and 11.0 (2)° with the thiophene and benzene rings, respectively. The dihedral angle between the aromatic rings is 3.47 (16)°. The carbon atoms of the methoxy groups are close to co-planar with their attached benzene ring [displacements of 0.033 (5) and 0.100 (5)Å for C14 and C15, respectively]. Otherwise, the bond lengths for (I) fall within their expected ranges (Allen et al., 1987) and are similar to those in a related structure (Jasinski et al., 2010).

In the crystal, three weak C—H···O and one C—H···Cl interactions (Table 1) link the molecules. Considered individually, they generate the following motifs: the C3—H3 bond generates inversion dimers containing R₂²(14) rings, whereas the C12—H12 bond leads to C(11) chains propagating in [010]. The methyl-H bonds lead to inversion-generated R₂²(24) loops (for C15—H15B) and C(11) chains (for C14—H14A). Taken together, these four interactions generate a three-dimensional network. Weak aromatic π-π stacking [centroid-centroid separations = 3.6823 (15) and 3.8722 (15) Å] may also help to consolidate the packing.

Related literature top

For a related structure and background references, see: Jasinski et al. (2010). For reference structural data, see: Allen et al. (1987).

Experimental top

2,5-Dichloro-3-acetylthiophene was obtained as a gift sample from SeQuent Scientific ltd., New Mangalore, India. 1-(2,5-Dichlorothiophen-3-yl)ethanone (1.95 g, 0.01 mol) was mixed with 3,4-dimethoxybenzaldehyde (1.66 g, 0.01 mol) and dissolved in ethanol (30 ml). To this, 3 ml of 50% KOH was added. The reaction mixture was stirred for 6 h. The resulting crude solid was filtered, washed successively with distilled water and finally recrystallized from ethanol (95%) to give the pure chalcone. Irregular yellow crystals of (I) were obtained by the slow evaporation of DMF solution (m.p.: 389–391 K).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: COLLECT (Nonius, 1998); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 ( Farrugia (1997); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. View of the molecular structure of (I) showing 50% displacement ellipsoids (arbitrary spheres for the H atoms).

(E)-1-(2,5-Dichloro-3-thienyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₅H₁₂Cl₂O₃S	F(000) = 704
M_r = 343.21	D_x = 1.531 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 20728 reflections
a = 8.9331 (2) Å	θ = 2.9–27.5°
b = 8.9997 (2) Å	µ = 0.58 mm⁻¹
c = 18.8210 (5) Å	T = 120 K
β = 100.181 (1)°	Fragment, yellow
V = 1489.29 (6) Å³	0.24 × 0.12 × 0.10 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	3424 independent reflections
Radiation source: fine-focus sealed tube	2834 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ω and ϕ scans	θ_max = 27.6°, θ_min = 3.2°
Absorption correction: multi-scan [SADABS (Bruker, 2003) and Blessing (1995)]	h = −11→11
T_min = 0.873, T_max = 0.944	k = −11→11
22032 measured reflections	l = −24→24

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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.034P)² + 1.9239P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
3424 reflections	Δρ_max = 0.72 e Å⁻³
193 parameters	Δρ_min = −0.41 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: 0.011 (2)

Crystal data top

C₁₅H₁₂Cl₂O₃S	V = 1489.29 (6) Å³
M_r = 343.21	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.9331 (2) Å	µ = 0.58 mm⁻¹
b = 8.9997 (2) Å	T = 120 K
c = 18.8210 (5) Å	0.24 × 0.12 × 0.10 mm
β = 100.181 (1)°

Data collection top

Nonius KappaCCD diffractometer	3424 independent reflections
Absorption correction: multi-scan [SADABS (Bruker, 2003) and Blessing (1995)]	2834 reflections with I > 2σ(I)
T_min = 0.873, T_max = 0.944	R_int = 0.056
22032 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.10	Δρ_max = 0.72 e Å⁻³
3424 reflections	Δρ_min = −0.41 e Å⁻³
193 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
C1	0.4943 (3)	0.2226 (3)	0.72975 (12)	0.0218 (5)
C2	0.5681 (3)	0.2506 (3)	0.67246 (14)	0.0253 (5)
H2	0.6632	0.2050	0.6705	0.030*
C3	0.5013 (3)	0.3471 (3)	0.61723 (14)	0.0273 (5)
H3	0.5512	0.3644	0.5774	0.033*
C4	0.3644 (3)	0.4175 (3)	0.61939 (13)	0.0248 (5)
C5	0.2908 (3)	0.3901 (3)	0.67817 (13)	0.0227 (5)
H5	0.1977	0.4388	0.6809	0.027*
C6	0.3533 (3)	0.2927 (3)	0.73192 (12)	0.0207 (5)
C7	0.2948 (3)	0.5123 (3)	0.55890 (14)	0.0269 (5)
H7	0.3459	0.5142	0.5187	0.032*
C8	0.1686 (3)	0.5971 (3)	0.55235 (13)	0.0232 (5)
H8	0.1154	0.6027	0.5918	0.028*
C9	0.1115 (3)	0.6799 (3)	0.48719 (13)	0.0230 (5)
C10	−0.0865 (3)	0.8706 (3)	0.43372 (13)	0.0217 (5)
C11	−0.0291 (3)	0.7698 (3)	0.48589 (12)	0.0213 (5)
C12	−0.1241 (3)	0.7591 (3)	0.53941 (13)	0.0265 (5)
H12	−0.1035	0.6955	0.5803	0.032*
C13	−0.2457 (3)	0.8490 (3)	0.52538 (14)	0.0298 (6)
C14	0.6852 (3)	0.0533 (3)	0.78546 (16)	0.0382 (7)
H14A	0.7073	−0.0128	0.8274	0.057*
H14B	0.7672	0.1264	0.7875	0.057*
H14C	0.6776	−0.0053	0.7411	0.057*
C15	0.1441 (3)	0.3186 (3)	0.79360 (15)	0.0317 (6)
H15A	0.1087	0.2819	0.8368	0.047*
H15B	0.0709	0.2905	0.7505	0.047*
H15C	0.1532	0.4270	0.7960	0.047*
O1	0.5440 (2)	0.1289 (2)	0.78610 (9)	0.0284 (4)
O2	0.28886 (19)	0.25494 (19)	0.78990 (9)	0.0265 (4)
O3	0.1727 (2)	0.6738 (2)	0.43354 (10)	0.0417 (5)
S1	−0.25196 (7)	0.95280 (7)	0.44816 (4)	0.02811 (19)
Cl1	−0.01562 (8)	0.92675 (7)	0.35926 (3)	0.03212 (19)
Cl2	−0.38786 (8)	0.86816 (11)	0.57543 (4)	0.0513 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0237 (11)	0.0212 (12)	0.0189 (11)	−0.0020 (9)	−0.0004 (9)	−0.0012 (9)
C2	0.0203 (11)	0.0268 (13)	0.0298 (13)	−0.0032 (10)	0.0076 (10)	−0.0045 (10)
C3	0.0309 (13)	0.0281 (13)	0.0250 (13)	−0.0083 (11)	0.0105 (10)	0.0000 (10)
C4	0.0299 (13)	0.0216 (12)	0.0238 (12)	−0.0040 (10)	0.0073 (10)	0.0007 (10)
C5	0.0266 (12)	0.0204 (12)	0.0213 (12)	−0.0007 (9)	0.0050 (10)	−0.0023 (9)
C6	0.0256 (11)	0.0190 (11)	0.0182 (11)	−0.0033 (9)	0.0056 (9)	−0.0021 (9)
C7	0.0264 (12)	0.0298 (14)	0.0260 (13)	−0.0011 (10)	0.0084 (10)	0.0025 (10)
C8	0.0204 (11)	0.0237 (12)	0.0267 (12)	0.0006 (9)	0.0074 (10)	−0.0039 (10)
C9	0.0220 (11)	0.0271 (13)	0.0208 (12)	0.0034 (10)	0.0062 (9)	−0.0009 (10)
C10	0.0195 (11)	0.0242 (12)	0.0211 (12)	0.0005 (9)	0.0025 (9)	−0.0032 (9)
C11	0.0213 (11)	0.0247 (12)	0.0180 (11)	0.0003 (9)	0.0040 (9)	−0.0030 (9)
C12	0.0261 (12)	0.0357 (14)	0.0181 (12)	0.0048 (11)	0.0051 (10)	−0.0003 (10)
C13	0.0265 (12)	0.0410 (15)	0.0232 (13)	0.0034 (11)	0.0077 (10)	−0.0050 (11)
C14	0.0296 (14)	0.0439 (17)	0.0400 (16)	0.0158 (12)	0.0033 (12)	0.0039 (13)
C15	0.0320 (13)	0.0358 (15)	0.0307 (14)	0.0038 (11)	0.0152 (11)	−0.0037 (11)
O1	0.0297 (9)	0.0313 (10)	0.0242 (9)	0.0095 (8)	0.0045 (7)	0.0036 (7)
O2	0.0308 (9)	0.0277 (9)	0.0230 (9)	0.0043 (7)	0.0106 (7)	0.0036 (7)
O3	0.0426 (11)	0.0582 (14)	0.0277 (10)	0.0238 (10)	0.0159 (9)	0.0103 (9)
S1	0.0233 (3)	0.0303 (4)	0.0296 (3)	0.0064 (3)	0.0016 (2)	−0.0019 (3)
Cl1	0.0378 (4)	0.0324 (4)	0.0278 (3)	−0.0019 (3)	0.0102 (3)	0.0059 (3)
Cl2	0.0363 (4)	0.0820 (6)	0.0411 (4)	0.0219 (4)	0.0215 (3)	0.0036 (4)

Geometric parameters (Å, º) top

C1—O1	1.367 (3)	C9—C11	1.491 (3)
C1—C2	1.383 (3)	C10—C11	1.368 (3)
C1—C6	1.415 (3)	C10—Cl1	1.713 (2)
C2—C3	1.404 (4)	C10—S1	1.717 (2)
C2—H2	0.9500	C11—C12	1.430 (3)
C3—C4	1.385 (4)	C12—C13	1.343 (4)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.405 (3)	C13—Cl2	1.718 (3)
C4—C7	1.470 (3)	C13—S1	1.720 (3)
C5—C6	1.380 (3)	C14—O1	1.435 (3)
C5—H5	0.9500	C14—H14A	0.9800
C6—O2	1.364 (3)	C14—H14B	0.9800
C7—C8	1.348 (3)	C14—H14C	0.9800
C7—H7	0.9500	C15—O2	1.427 (3)
C8—C9	1.448 (3)	C15—H15A	0.9800
C8—H8	0.9500	C15—H15B	0.9800
C9—O3	1.231 (3)	C15—H15C	0.9800

O1—C1—C2	125.7 (2)	C11—C10—Cl1	129.58 (18)
O1—C1—C6	114.9 (2)	C11—C10—S1	113.31 (18)
C2—C1—C6	119.4 (2)	Cl1—C10—S1	117.10 (14)
C1—C2—C3	119.4 (2)	C10—C11—C12	110.9 (2)
C1—C2—H2	120.3	C10—C11—C9	125.4 (2)
C3—C2—H2	120.3	C12—C11—C9	123.7 (2)
C4—C3—C2	121.5 (2)	C13—C12—C11	112.4 (2)
C4—C3—H3	119.2	C13—C12—H12	123.8
C2—C3—H3	119.2	C11—C12—H12	123.8
C3—C4—C5	118.8 (2)	C12—C13—Cl2	127.1 (2)
C3—C4—C7	119.9 (2)	C12—C13—S1	113.43 (19)
C5—C4—C7	121.3 (2)	Cl2—C13—S1	119.47 (16)
C6—C5—C4	120.3 (2)	O1—C14—H14A	109.5
C6—C5—H5	119.9	O1—C14—H14B	109.5
C4—C5—H5	119.9	H14A—C14—H14B	109.5
O2—C6—C5	124.9 (2)	O1—C14—H14C	109.5
O2—C6—C1	114.6 (2)	H14A—C14—H14C	109.5
C5—C6—C1	120.6 (2)	H14B—C14—H14C	109.5
C8—C7—C4	129.2 (2)	O2—C15—H15A	109.5
C8—C7—H7	115.4	O2—C15—H15B	109.5
C4—C7—H7	115.4	H15A—C15—H15B	109.5
C7—C8—C9	122.1 (2)	O2—C15—H15C	109.5
C7—C8—H8	118.9	H15A—C15—H15C	109.5
C9—C8—H8	118.9	H15B—C15—H15C	109.5
O3—C9—C8	122.1 (2)	C1—O1—C14	116.9 (2)
O3—C9—C11	120.4 (2)	C6—O2—C15	116.97 (19)
C8—C9—C11	117.5 (2)	C10—S1—C13	89.97 (12)

O1—C1—C2—C3	178.3 (2)	S1—C10—C11—C12	0.2 (3)
C6—C1—C2—C3	−0.5 (4)	Cl1—C10—C11—C9	−2.3 (4)
C1—C2—C3—C4	1.3 (4)	S1—C10—C11—C9	179.10 (19)
C2—C3—C4—C5	−0.5 (4)	O3—C9—C11—C10	−12.1 (4)
C2—C3—C4—C7	−177.2 (2)	C8—C9—C11—C10	170.1 (2)
C3—C4—C5—C6	−1.1 (4)	O3—C9—C11—C12	166.6 (3)
C7—C4—C5—C6	175.6 (2)	C8—C9—C11—C12	−11.1 (4)
C4—C5—C6—O2	−177.8 (2)	C10—C11—C12—C13	0.4 (3)
C4—C5—C6—C1	1.9 (4)	C9—C11—C12—C13	−178.6 (2)
O1—C1—C6—O2	−0.3 (3)	C11—C12—C13—Cl2	179.3 (2)
C2—C1—C6—O2	178.7 (2)	C11—C12—C13—S1	−0.8 (3)
O1—C1—C6—C5	179.9 (2)	C2—C1—O1—C14	0.1 (4)
C2—C1—C6—C5	−1.1 (3)	C6—C1—O1—C14	178.9 (2)
C3—C4—C7—C8	−175.4 (3)	C5—C6—O2—C15	1.8 (3)
C5—C4—C7—C8	8.0 (4)	C1—C6—O2—C15	−178.0 (2)
C4—C7—C8—C9	−177.4 (2)	C11—C10—S1—C13	−0.5 (2)
C7—C8—C9—O3	2.2 (4)	Cl1—C10—S1—C13	−179.29 (16)
C7—C8—C9—C11	179.9 (2)	C12—C13—S1—C10	0.7 (2)
Cl1—C10—C11—C12	178.78 (19)	Cl2—C13—S1—C10	−179.34 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.95	2.53	3.227 (3)	130
C12—H12···O1ⁱⁱ	0.95	2.55	3.441 (3)	157
C14—H14A···O3ⁱⁱⁱ	0.98	2.53	3.474 (3)	161
C15—H15B···Cl1^iv	0.98	2.82	3.647 (3)	142

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y+1/2, −z+3/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂Cl₂O₃S
M_r	343.21
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	8.9331 (2), 8.9997 (2), 18.8210 (5)
β (°)	100.181 (1)
V (Å³)	1489.29 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.58
Crystal size (mm)	0.24 × 0.12 × 0.10

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan [SADABS (Bruker, 2003) and Blessing (1995)]
T_min, T_max	0.873, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	22032, 3424, 2834
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.113, 1.10
No. of reflections	3424
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.41

Computer programs: COLLECT (Nonius, 1998), DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 ( Farrugia (1997), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.95	2.53	3.227 (3)	130
C12—H12···O1ⁱⁱ	0.95	2.55	3.441 (3)	157
C14—H14A···O3ⁱⁱⁱ	0.98	2.53	3.474 (3)	161
C15—H15B···Cl1^iv	0.98	2.82	3.647 (3)	142

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y+1/2, −z+3/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x, −y+1, −z+1.

Acknowledgements

CSC thanks the University of Mysore for providing research facilities. HSY thanks the University of Mysore for sanctioning sabbatical leave.

References

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