Crystal structure and Hirshfeld surface analysis of (2E)-3-(3-chloro­phen­yl)-1-(3,4-di­meth­oxy­phen­yl)prop-2-en-1-one

Sheshadri, S.N.; Atioğlu, Z.; Akkurt, M.; Chidan Kumar, C.S.; Quah, C.K.; Siddaraju, B.P.; Veeraiah, M.K.

doi:10.1107/S205698901800837X

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ISSN: 2056-9890

Volume 74| Part 7| July 2018| Pages 935-938

https://doi.org/10.1107/S205698901800837X

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Crystal structure and Hirshfeld surface analysis of (2E)-3-(3-chlorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one

S. N. Sheshadri,^a Zeliha Atioğlu,^b Mehmet Akkurt,^c ^* C. S. Chidan Kumar,^d Ching Kheng Quah,^e B. P. Siddaraju ^f and M. K. Veeraiah ^g

^aDepartment of Chemistry, GSSS Institute of Engineering & Technology for Women, Mysuru 570 016, Karnataka, India, ^bİlke Education and Health Foundation, Cappadocia University, Cappadocia Vocational College, The Medical Imaging Techniques Program, 50420 Mustafapaşa, Ürgüp, Nevşehir, Turkey, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^dDepartment of Engineering Chemistry, Vidya Vikas Institute of Engineering & Technology, Visvesvaraya Technological University, Alanahalli, Mysuru 570 028, Karnataka, India, ^eX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^fDepartment of Chemistry, Cauvery Institute of Technology, Mandya 571 402, Karnataka, India, and ^gDepartment of Chemistry, Sri Siddhartha Institute of Technology, Tumkur 572 105, Karnataka, India
^*Correspondence e-mail: akkurt@erciyes.edu.tr

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 25 May 2018; accepted 6 June 2018; online 8 June 2018)

In title compound, C₁₇H₁₅ClO₃, the dihedral angle between the benzene and chlorophenyl rings is 18.46 (7)°. In the crystal, molecules are linked by C—H⋯O hydrogen contacts, enclosing an R²₂(14) ring motif, and by a further C—H⋯O hydrogen contact, forming a two-dimensional supramolecular structure extending along the direction parallel to the ac plane. Hirshfeld surface analysis shows that van der Waals interactions constitute the major contribution to the intermolecular interactions, with H⋯H contacts accounting for 36.2% of the surface.

Keywords: crystal structure; 3,4-dimethoxyphenyl ring; 3-chlorophenyl ring; Hirshfeld surface analysis; hydrogen contacts; ring motif.

CCDC reference: 1847705

1. Chemical context

Materials exhibiting two photon absorption (TPA) have wide applications such as frequency-up lasing, multi-photon microscopy, three-dimensional fluorescence imaging, eye and sensor protection. Materials with potential non-linear optical (NLO) properties have significant applications in the field of photonics. Chalcone and its derivatives have attracted significant attention in the past few years because of their availability of high optical non-linearities resulting from the significant delocalization of π-conjugated electron clouds throughout the chalcone system, providing a large charge-transfer axis with appropriate substituents on the terminal aromatic rings. The second harmonic generation (SHG) efficiency of these compounds is due to the strong intermolecular electron–donor–acceptor interactions, which may also enhance the non-linear optical (NLO) properties. With the possibility of developing low-cost, large-area and flexible electronic devices, π-conjugated systems have been studied extensively for their optoelectronic properties (Chandra Shekhara Shetty et al., 2016 , 2017 ).

2. Structural commentary

The molecular structure of the title compound is shown in Fig. 1. The title compound is constructed from two aromatic rings (chlorophenyl and terminal methoxyphenyl rings), which are linked by a C=C—C(=O)—C enone bridge. Compared to the nearly coplanar arrangement of rings in the title compound, the molecule is twisted substantially [C5—C6—C7—O3 = 3.5 (2) ° and O3—C7—C8—C9 = 10.5 (2) °] about the enone bridge, which may arise from steric repulsion with the ortho-O2 atom. Hence, the dihedral angle between the 3,4-methoxyphenyl and chlorophenyl rings increases to 18.46 (7)°. The C atoms of the methoxy groups are close to the plane of their attached ring: deviations of C16 and C17 are 0.252 (2) and 0.038 (2) Å, respectively. The bond lengths and angles are comparable with those in the similar compounds (E)-3-(3,4-dimethoxyphenyl)-1-(1-hydroxynaphthalen-2yl)prop-2-en-1-one (Ezhilarasi et al., 2015 ), (E)-1-(3-bromophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one (Escobar et al., 2012 ) and (E)-3-(2-bromophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one (Li et al., 2012 ).

Figure 1
The molecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level.

3. Supramolecular features and Hirshfeld surface analysis

In the crystal, molecules are linked by C—H⋯O hydrogen contacts (Table 1, Fig. 2), enclosing an $[R_{2}^{2}]$ (14) ring motif, and by a further C—H⋯O hydrogen contact, forming a three-dimensional structure extending in the a- and c-axis directions.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O3ⁱ	0.93	2.54	3.417 (2)	157
C15—H15A⋯O2ⁱⁱ	0.93	2.54	3.4378 (18)	163
Symmetry codes: (i) ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
A view along the a axis of the crystal packing of the title compound. Intermolecular interactions are shown as dashed lines.

Hirshfeld surfaces and fingerprint plots were generated for the title compound based on the crystallographic information file (CIF) using CrystalExplorer (McKinnon et al., 2007 ). Hirshfeld surfaces enable the visualization of intermolecular interactions by different colors and color intensity, representing short or long contacts and indicating the relative strength of the interactions. Figs. 3 and 4 show the Hirshfeld surfaces mapped over d_norm(−0.16 to 1.25 a.u.) and shape-index (−1.0 to 1.0 a.u.).

Figure 3
View of the three-dimensional Hirshfeld surface of the title compound mapped over d_norm.

Figure 4
Hirshfeld surface of the title complex plotted over shape-index.

In Fig. 3, the spots near atoms O2 and O3 result from the C15—H15A⋯O2ⁱⁱ and C11—H11A⋯O3ⁱ interactions significant in the molecule packing of the title compound (Table 1). Some of the short intermolecular contacts for the title compound are listed in Table 2. The Hirshfeld surfaces illustrated in Fig. 3 also reflect the involvement of different atoms in the intermolecular interactions through the appearance of blue and red regions around the participating atoms, which correspond to positive and negative electrostatic potential, respectively.

Table 2
Summary of short interatomic contacts (Å) in the title compound

Contact	Distance	Symmetry operation
Cl1⋯H17B	3.05	−1 + x, 1 + y, z
Cl1⋯C1	3.4666 (15)	$[{1\over 2}]$ − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
O2⋯H15A	2.54	$[{3\over 2}]$ − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
O1⋯H17A	2.86	$[{5\over 2}]$ − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
H17C⋯C10	2.88	1 + x, y, z
H11A⋯O3	2.54	1 − x, 1 − y, −z
C1⋯Cl1	3.4666 (15)	$[{1\over 2}]$ − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
H15A⋯O2	2.54	$[{3\over 2}]$ − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
C10⋯H17C	2.88	−1 + x, y, z
C13⋯C13	3.497 (2)	−x, 2 − y, −z
H13A⋯H16A	2.46	− $[{3\over 2}]$ + x, $[{3\over 2}]$ − y, − $[{1\over 2}]$ + z
H16A⋯H13A	2.46	$[{3\over 2}]$ + x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z
H17A⋯O1	2.86	$[{5\over 2}]$ − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
H17B⋯Cl1	3.05	1 + x, −1 + y, z

The overall two-dimensional fingerprint plot for the title compound and those delineated into H⋯H, C⋯H/H⋯C, H⋯O/O⋯H, Cl⋯H/H⋯Cl and Cl⋯C/C⋯Cl contacts are illustrated in Fig. 5; the percentage contributions from the different interatomic contacts to the Hirshfeld surfaces are as follows: H⋯H (36.2%), C⋯H/H⋯C (24.6%), H⋯O/O⋯H (19.2%), Cl⋯H/H⋯Cl (10.5%), Cl⋯C/C⋯Cl (5.8%), C⋯C (3.3%), Cl⋯O/O⋯Cl (0.3%) and O⋯C/C⋯O (0.2%), as shown in the two-dimensional fingerprint plots in Fig. 4.

Figure 5
The two-dimensional fingerprint plots of the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) C⋯H, (d) O⋯H, (e) Cl⋯H and (f) Cl⋯C interactions [d_e and d_i represent the distances from a point on the Hirshfeld surface to the nearest atoms outside (external) and inside (internal) the surface, respectively].

4. Synthesis and crystallization

The reagents and solvents for the synthesis were obtained from the Aldrich Chemical Co. and were used without additional purification. 1-(3,4-Dimethoxyphenyl) ethanone (0.01 mol) and 3-chlorobenzaldehyde (0.01 mol) were dissolved in 20 ml methanol. A catalytic amount of NaOH was added to the solution dropwise with vigorous stirring. The reaction mixture was stirred for about 5–6 h at room temperature. The progress of the reaction was monitored by TLC. The formed crude products were filtered, washed successively with distilled water and recrystallized from ethanol to get the title chalcone. Crystals suitable for X-ray diffraction studies were obtained from acetone solution by slow evaporation at room temperature. The melting point (371–373 K) was determined by a Stuart Scientific (UK) apparatus. The purity of the compound was confirmed by thin layer chromatography using Merck silica gel 60 F254 coated aluminum plates.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. C-bound H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C) for C—H and C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C) for methyl H atoms.

Table 3
Experimental details

Crystal data
Chemical formula	C₁₇H₁₅ClO₃
M_r	302.74
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	9.0491 (4), 8.3257 (4), 20.2857 (9)
β (°)	99.484 (1)
V (Å³)	1507.44 (12)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.26
Crystal size (mm)	0.40 × 0.24 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD
No. of measured, independent and observed [I > 2σ(I)] reflections	39332, 5506, 3732
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.758

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.158, 1.01
No. of reflections	5506
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.43
Computer programs: APEX2 and SAINT (Bruker, 2007 ), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1847705

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S205698901800837X/xu5927sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901800837X/xu5927Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698901800837X/xu5927Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

(2E)-3-(3-Chlorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₇H₁₅ClO₃	F(000) = 632
M_r = 302.74	D_x = 1.334 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8862 reflections
a = 9.0491 (4) Å	θ = 2.7–30.8°
b = 8.3257 (4) Å	µ = 0.26 mm⁻¹
c = 20.2857 (9) Å	T = 294 K
β = 99.484 (1)°	Block, yellow
V = 1507.44 (12) Å³	0.40 × 0.24 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	R_int = 0.036
φ and ω scans	θ_max = 32.6°, θ_min = 2.0°
39332 measured reflections	h = −13→13
5506 independent reflections	k = −12→12
3732 reflections with I > 2σ(I)	l = −30→30

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.158	w = 1/[σ²(F_o²) + (0.0758P)² + 0.3034P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
5506 reflections	Δρ_max = 0.31 e Å⁻³
190 parameters	Δρ_min = −0.43 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	−0.02901 (5)	1.02517 (6)	0.15452 (2)	0.0710 (2)
O1	1.07019 (12)	0.65283 (15)	0.35402 (5)	0.0576 (3)
O2	1.13649 (12)	0.52216 (16)	0.24887 (6)	0.0634 (4)
O3	0.67255 (12)	0.57110 (17)	0.07167 (5)	0.0632 (4)
C1	0.72153 (15)	0.73479 (17)	0.23869 (7)	0.0458 (4)
C2	0.82535 (15)	0.73642 (17)	0.29717 (7)	0.0463 (4)
C3	0.96267 (14)	0.66310 (15)	0.29901 (6)	0.0420 (3)
C4	0.99836 (14)	0.59071 (16)	0.24086 (6)	0.0415 (3)
C5	0.89499 (14)	0.59023 (15)	0.18335 (6)	0.0405 (3)
C6	0.75372 (13)	0.66142 (14)	0.18154 (6)	0.0394 (3)
C7	0.64331 (14)	0.64884 (17)	0.11929 (7)	0.0444 (4)
C8	0.49469 (15)	0.72588 (18)	0.11575 (7)	0.0495 (4)
C9	0.38379 (15)	0.69300 (18)	0.06640 (6)	0.0452 (4)
C10	0.22936 (14)	0.75164 (16)	0.05882 (6)	0.0424 (3)
C11	0.12555 (17)	0.69543 (19)	0.00574 (7)	0.0525 (4)
C12	−0.02283 (18)	0.7421 (2)	−0.00148 (8)	0.0610 (5)
C13	−0.07040 (16)	0.8446 (2)	0.04383 (8)	0.0564 (5)
C14	0.03261 (16)	0.90063 (17)	0.09633 (7)	0.0470 (4)
C15	0.18120 (15)	0.85720 (16)	0.10468 (7)	0.0447 (3)
C16	1.0326 (2)	0.7046 (3)	0.41599 (8)	0.0826 (7)
C17	1.1814 (2)	0.4431 (2)	0.19409 (9)	0.0669 (6)
H1A	0.62888	0.78375	0.23788	0.0550*
H2A	0.80242	0.78689	0.33512	0.0560*
H5A	0.91867	0.54216	0.14504	0.0490*
H8A	0.47900	0.79854	0.14872	0.0590*
H9A	0.40642	0.62539	0.03295	0.0540*
H11A	0.15612	0.62577	−0.02523	0.0630*
H12A	−0.09113	0.70376	−0.03734	0.0730*
H13A	−0.17036	0.87545	0.03911	0.0680*
H15A	0.24886	0.89746	0.14035	0.0540*
H16A	1.11764	0.69130	0.45069	0.1240*
H16B	1.00432	0.81587	0.41282	0.1240*
H16C	0.95044	0.64175	0.42628	0.1240*
H17A	1.28064	0.40096	0.20705	0.1000*
H17B	1.11330	0.35669	0.17988	0.1000*
H17C	1.18073	0.51778	0.15799	0.1000*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0650 (3)	0.0704 (3)	0.0809 (3)	0.0083 (2)	0.0216 (2)	−0.0176 (2)
O1	0.0518 (6)	0.0735 (7)	0.0440 (5)	0.0124 (5)	−0.0028 (4)	−0.0031 (5)
O2	0.0487 (6)	0.0881 (8)	0.0518 (6)	0.0278 (5)	0.0039 (4)	−0.0044 (5)
O3	0.0479 (6)	0.0898 (8)	0.0505 (6)	0.0088 (5)	0.0038 (4)	−0.0226 (6)
C1	0.0400 (6)	0.0500 (7)	0.0472 (7)	0.0080 (5)	0.0064 (5)	−0.0052 (5)
C2	0.0462 (7)	0.0506 (7)	0.0420 (6)	0.0063 (5)	0.0074 (5)	−0.0069 (5)
C3	0.0425 (6)	0.0424 (6)	0.0398 (6)	0.0012 (5)	0.0028 (5)	0.0021 (5)
C4	0.0382 (6)	0.0423 (6)	0.0441 (6)	0.0057 (5)	0.0073 (5)	0.0033 (5)
C5	0.0404 (6)	0.0425 (6)	0.0396 (6)	0.0032 (5)	0.0093 (5)	−0.0010 (5)
C6	0.0382 (6)	0.0393 (5)	0.0403 (6)	0.0007 (4)	0.0057 (4)	−0.0005 (4)
C7	0.0384 (6)	0.0510 (7)	0.0434 (6)	0.0014 (5)	0.0055 (5)	−0.0046 (5)
C8	0.0426 (6)	0.0562 (8)	0.0476 (7)	0.0070 (6)	0.0014 (5)	−0.0090 (6)
C9	0.0424 (6)	0.0539 (7)	0.0388 (6)	0.0028 (5)	0.0050 (5)	−0.0017 (5)
C10	0.0401 (6)	0.0469 (6)	0.0384 (6)	−0.0001 (5)	0.0011 (5)	0.0006 (5)
C11	0.0493 (7)	0.0603 (8)	0.0449 (7)	0.0006 (6)	−0.0014 (6)	−0.0093 (6)
C12	0.0468 (8)	0.0733 (10)	0.0568 (8)	−0.0030 (7)	−0.0092 (6)	−0.0092 (7)
C13	0.0379 (6)	0.0642 (9)	0.0643 (9)	0.0002 (6)	−0.0002 (6)	0.0022 (7)
C14	0.0452 (7)	0.0445 (6)	0.0519 (7)	−0.0005 (5)	0.0094 (5)	0.0004 (5)
C15	0.0419 (6)	0.0476 (6)	0.0427 (6)	−0.0022 (5)	0.0016 (5)	−0.0030 (5)
C16	0.0814 (12)	0.1149 (17)	0.0452 (8)	0.0267 (12)	−0.0080 (8)	−0.0161 (10)
C17	0.0583 (9)	0.0781 (11)	0.0673 (10)	0.0238 (8)	0.0189 (8)	−0.0001 (8)

Geometric parameters (Å, º) top

Cl1—C14	1.7310 (15)	C12—C13	1.374 (2)
O1—C3	1.3570 (16)	C13—C14	1.376 (2)
O1—C16	1.422 (2)	C14—C15	1.376 (2)
O2—C4	1.3593 (17)	C1—H1A	0.9300
O2—C17	1.408 (2)	C2—H2A	0.9300
O3—C7	1.2273 (18)	C5—H5A	0.9300
C1—C2	1.387 (2)	C8—H8A	0.9300
C1—C6	1.3832 (18)	C9—H9A	0.9300
C2—C3	1.3794 (19)	C11—H11A	0.9300
C3—C4	1.4088 (17)	C12—H12A	0.9300
C4—C5	1.3698 (17)	C13—H13A	0.9300
C5—C6	1.4041 (17)	C15—H15A	0.9300
C6—C7	1.4792 (18)	C16—H16A	0.9600
C7—C8	1.4810 (19)	C16—H16B	0.9600
C8—C9	1.3241 (19)	C16—H16C	0.9600
C9—C10	1.4643 (19)	C17—H17A	0.9600
C10—C11	1.3884 (19)	C17—H17B	0.9600
C10—C15	1.4005 (19)	C17—H17C	0.9600
C11—C12	1.382 (2)

C3—O1—C16	117.66 (12)	C6—C1—H1A	120.00
C4—O2—C17	118.77 (12)	C1—C2—H2A	120.00
C2—C1—C6	120.98 (13)	C3—C2—H2A	120.00
C1—C2—C3	119.94 (13)	C4—C5—H5A	120.00
O1—C3—C2	124.80 (12)	C6—C5—H5A	120.00
O1—C3—C4	115.43 (11)	C7—C8—H8A	119.00
C2—C3—C4	119.77 (12)	C9—C8—H8A	119.00
O2—C4—C3	114.38 (11)	C8—C9—H9A	116.00
O2—C4—C5	125.88 (12)	C10—C9—H9A	117.00
C3—C4—C5	119.72 (12)	C10—C11—H11A	120.00
C4—C5—C6	120.80 (11)	C12—C11—H11A	120.00
C1—C6—C5	118.76 (11)	C11—C12—H12A	120.00
C1—C6—C7	122.74 (11)	C13—C12—H12A	120.00
C5—C6—C7	118.45 (11)	C12—C13—H13A	121.00
O3—C7—C6	120.42 (12)	C14—C13—H13A	121.00
O3—C7—C8	120.14 (13)	C10—C15—H15A	120.00
C6—C7—C8	119.40 (12)	C14—C15—H15A	120.00
C7—C8—C9	121.08 (13)	O1—C16—H16A	109.00
C8—C9—C10	127.00 (13)	O1—C16—H16B	109.00
C9—C10—C11	118.76 (12)	O1—C16—H16C	109.00
C9—C10—C15	122.38 (12)	H16A—C16—H16B	109.00
C11—C10—C15	118.81 (12)	H16A—C16—H16C	109.00
C10—C11—C12	120.58 (14)	H16B—C16—H16C	109.00
C11—C12—C13	120.63 (15)	O2—C17—H17A	109.00
C12—C13—C14	118.77 (14)	O2—C17—H17B	109.00
Cl1—C14—C13	118.53 (11)	O2—C17—H17C	109.00
Cl1—C14—C15	119.45 (11)	H17A—C17—H17B	109.00
C13—C14—C15	122.00 (13)	H17A—C17—H17C	110.00
C10—C15—C14	119.21 (13)	H17B—C17—H17C	109.00
C2—C1—H1A	120.00

C16—O1—C3—C2	7.7 (2)	C1—C6—C7—C8	3.84 (19)
C16—O1—C3—C4	−171.77 (15)	C5—C6—C7—O3	3.5 (2)
C17—O2—C4—C3	178.44 (13)	C5—C6—C7—C8	−178.75 (12)
C17—O2—C4—C5	0.3 (2)	O3—C7—C8—C9	10.5 (2)
C6—C1—C2—C3	−0.5 (2)	C6—C7—C8—C9	−167.28 (13)
C2—C1—C6—C5	−1.0 (2)	C7—C8—C9—C10	175.76 (13)
C2—C1—C6—C7	176.44 (13)	C8—C9—C10—C11	−175.75 (15)
C1—C2—C3—O1	−177.65 (13)	C8—C9—C10—C15	1.6 (2)
C1—C2—C3—C4	1.8 (2)	C9—C10—C11—C12	177.04 (14)
O1—C3—C4—O2	−0.40 (17)	C15—C10—C11—C12	−0.4 (2)
O1—C3—C4—C5	177.86 (12)	C9—C10—C15—C14	−176.57 (13)
C2—C3—C4—O2	−179.87 (12)	C11—C10—C15—C14	0.8 (2)
C2—C3—C4—C5	−1.60 (19)	C10—C11—C12—C13	−0.2 (2)
O2—C4—C5—C6	178.20 (13)	C11—C12—C13—C14	0.4 (2)
C3—C4—C5—C6	0.2 (2)	C12—C13—C14—Cl1	−178.21 (12)
C4—C5—C6—C1	1.13 (19)	C12—C13—C14—C15	0.0 (2)
C4—C5—C6—C7	−176.39 (12)	Cl1—C14—C15—C10	177.64 (10)
C1—C6—C7—O3	−173.88 (14)	C13—C14—C15—C10	−0.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O3	0.93	2.45	2.7888 (18)	102
C11—H11A···O3ⁱ	0.93	2.54	3.417 (2)	157
C15—H15A···O2ⁱⁱ	0.93	2.54	3.4378 (18)	163

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

Summary of short interatomic contacts (Å) in the title compound top

Contact	Distance	Symmetry operation
Cl1···H17B	3.05	-1 + x, 1 + y, z
Cl1···C1	3.4666 (15)	1/2 - x, 1/2 + y, 1/2 - z
O2···H15A	2.54	3/2 - x, -1/2 + y, 1/2 - z
O1···H17A	2.86	5/2 - x, 1/2 + y, 1/2 - z
H17C···C10	2.88	1 + x, y, z
H11A···O3	2.54	1 - x, 1 - y, -z
C1···Cl1	3.4666 (15)	1/2 - x, -1/2 + y, 1/2 - z
H15A···O2	2.54	3/2 - x, 1/2 + y, 1/2 - z
C10···H17C	2.88	-1 + x, y, z
C13···C13	3.497 (2)	-x, 2 - y, -z
H13A···H16A	2.46	-3/2 + x, 3/2 - y, - 1/2 + z
H16A···H13A	2.46	3/2 + x, 3/2 - y, 1/2 + z
H17A···O1	2.86	5/2 - x, -1/2 + y, 1/2 - z
H17B···Cl1	3.05	1 + x, -1 + y, z

Acknowledgements

The authors extend their appreciation to the Vidya Vikas Research & Development Centre for the facilities and their encouragement.

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