Ethyl 6-(4-chloro­phen­yl)-2,2-dimethyl-4-oxo-3,4-di­hydro-2H-pyran-5-carboxyl­ate

Sharmila, N.; Sundar, T.V.; Sakthivel, P.; Venkatesan, P.

doi:10.1107/S2414314617000347

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 1| January 2017| x170034

https://doi.org/10.1107/S2414314617000347

Open

access

Ethyl 6-(4-chlorophenyl)-2,2-dimethyl-4-oxo-3,4-dihydro-2H-pyran-5-carboxylate

N. Sharmila,^a T. V. Sundar,^a ^* P. Sakthivel ^b and P. Venkatesan ^c

^aPostgraduate and Research Department of Physics, National College (Autonomous), Tiruchirappalli 620 001, Tamilnadu, India, ^bSchool of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, Tamilnadu, India, and ^cLaboratorio de Políimeros, Centro de Química Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla (BUAP), Complejo de Ciencias, ICUAP, Edif. 103H, 22 Sur y San Claudio, CP 72570 Puebla, Puebla, Mexico
^*Correspondence e-mail: sunvag@gmail.com

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 23 December 2016; accepted 9 January 2017; online 13 January 2017)

The title compound, C₁₆H₁₇ClO₄, is a derivative of 3,4-dihydro-2H-pyran-4-one in which the root moiety forms a dihedral angle of 49.36 (5)° with the pendent chlorobenzene ring. The crystal structure features weak methyl-C—H⋯O(ring carbonyl) contacts, leading to an R²₂(12) ring motif, and benzene-C—H⋯O(ester) interactions, leading to a supramolecular chain along the b axis, to form a three-dimensional network.

Keywords: crystal structure; pyran-4-one; C—H⋯O interactions.

CCDC reference: 1526174

Structure description

4H-Pyran-4-ones and their various derivatives are known for their significant biological and pharmacological activities, and are structurally similar to biologically active 1,4-dihydropyridines (1,4-DHPs) (Zonouz et al., 2014 ). They act as calcium antagonists (Súarez et al., 2002 ) and serve as potent apoptosis inducers (Zhang et al., 2005 ). As a continuation of structural investigations of a series of 4H-pyran-4-one derivatives, we report herein on the crystal structure determination and the geometry optimization of the title compound, (I).

A perspective view of (I) with the atomic numbering scheme is illustrated in Fig. 1. The 3,4-dihydro-2H-pyran-4-one moiety (C7–C11/O1/O2) forms a dihedral angle of 49.36 (5)° with the benzene ring. The bond distances and angles are essentially equivalent compared to those in the previously reported structure ethyl 2,2-dimethyl-4-oxo-6-phenyl-3,4-dihydro-2H-pyran-5-carboxylate (II) (Sharmila et al., 2016 ). However, the benzene group has rotated about the C6—C7 bond as evident from the change in torsion angles namely, C1—C6—C7—C11 and C5—C6—C7—C11 of −133.37 (15) and 50.56 (19)°, respectively, cf. 138.6 (2) and −43.3 (3)° in (II). Also, a fragment overlay (Gans & Shalloway, 2001 ) analysis of (I) with (II) gives an r.m.s. deviation of 2.91 Å (Fig. 2). These observations indicate that the structural changes could be attributed to the substitution of the heavier Cl atom at C3 and the involvement of C2 in making a hydrogen bond with O4 via H2 (Table 1). Another superposition analysis of (I) but, with 4-(4-fluorophenyl)-6-methylamino-5-nitro-2-phenyl-4H-pyran-3- carbonitrile (III) (Vishnupriya et al., 2013 ) gives an r.m.s. deviation of 1.57 Å, which confirms the effect of relatively heavier Cl substitution at C3 resulting in the small conformational changes in the molecule.

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O4ⁱ	0.93	2.66	3.3694 (18)	134
C15—H15B⋯O2ⁱⁱ	0.96	2.66	3.553 (2)	156
C13—H13B⋯Cgⁱⁱⁱ	0.97	2.96	3.6463 (17)	129
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z+1; (iii) x, y+1, z.

Figure 1
The molecular structure of (I), with displacement ellipsoids for the non-H atoms drawn at the 30% probability level.

Figure 2
A superimposed fit of (I) (green) and related structure (II) (black).

The pyran ring of (I) is puckered (puckering parameters: Q = 0.4539 (16) Å, q2 = 0.378 (15) Å, q3 = −0.2512 (15) Å, θ = 123.61 (19)° and φ = 91.6 (2)°, with atom C8 showing the maximum deviation of 0.2946 (16) Å from the plane defined by O1/C7/C11–C8.

Theoretical calculations of the molecular structure were performed using MOPAC2016′s PM7 geometry optimization algorithm (Stewart, 2016 ). This shows satisfactory agreement with the results of the X-ray crystal structure analysis. The HOMO and LUMO energy levels were found to be −9.829 and −1.127 eV, respectively. The total energy and dipole moment values of (I) are −3643.34886 eV and 5.235 Debye, respectively. In the geometry optimized structure of (I), a decrease in bond distances seems to be observed for the bonds O1—C8 (1.46 Å) and C6—C7 (1.47 Å) when compared to those in the crystal, i.e. 1.4732 (16) and 1.4832 (16) Å. The O1—C7—C6 bond angle decreased from 110.78 (11) to 110.2°, and the O1—C8—C9 bond angle increased from 108.65 (11) to 110.5°. The relative conformation about the bond joining the 3,4-dihydro-2H-pyran-4-one moiety with the chlorobenzene group of (I) is defined by the torsion angles C1—C6—C7—O1 and C5—C6—C7—O1 of 47.68 (17) and −128.38 (13)° in the crystal, i.e. show (+) syn-clinal and (−) anti-clinal conformations, respectively, and compare with 49.9 and −130.8° in the optimized structure. A superimposed fit of (I) with its energy-minimized molecule gives an r.m.s. deviation of 0.152 Å (Fig. 3).

Figure 3
A superimposed fit of (I) (red) and its energy-minimized counterpart (blue).

One of the methyl carbons, C15, is involved in hydrogen bond with O2 of a symmetry-related molecule via H15B to form a R₂²(12) ring motif. The phenyl carbon C2 is involved in an interaction with O4 of a symmetry-related molecule via H2 to form a chain along the b axis (Table 1 and Fig. 4). These combine to give a three-dimensional architecture. Further, a weak C—H⋯π interaction between C13 and the centroid (Cg) of the C1–C6 ring via H13B, provides additional stabilization to the crystal (Table 1).

Figure 4
Molecular packing of (I), showing the C—H⋯O interactions as dashed lines. Other H-atoms are omitted for clarity.

Synthesis and crystallization

To a solution of ethyl 3-(4-chlorophenyl)-3-oxopropanoate (226 mg, 1.0 mmol), CaCl₂ (11 mg, 0.1 mmol), triethylamine (278 µL, 2.0 mmol) and 3-methylbut-2-enoyl chloride (112 µL, 1.0 mmol), dichloromethane (4 ml) was added at ambient temperature. After completion of the addition, the reaction mixture was subjected to stirring at room temperature for 3 h. The progress of the reaction was monitored by thin-layer chromatography. The organic layer was separated, filtered and concentrated. The crude product was purified by silica gel column chromatography (EtOAc/hexane = 2:8 v/v as eluent). The product was a colourless solid (yield 90%, 277 mg) and was crystallized in hexane/EtOAc (6:4 v/v (m.p. 354–356 K).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₇ClO₄
M_r	308.74
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.4412 (3), 7.6959 (2), 20.2651 (5)
β (°)	102.311 (2)
V (Å³)	1590.94 (7)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.25
Crystal size (mm)	0.25 × 0.17 × 0.12

Data collection
Diffractometer	Bruker Smart CCD Area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2008 )
T_min, T_max	0.746, 0.845
No. of measured, independent and observed [I > 2σ(I)] reflections	15125, 3995, 2978
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.108, 1.03
No. of reflections	3995
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.26
Computer programs: SMART and SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), QMOL (Gans & Shalloway, 2001), Mercury (Macrae et al., 2008 ), ORTEPIII (Burnett & Johnson, 1996 ), WinGX publication routines (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1526174

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617000347/tk4027sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617000347/tk4027Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617000347/tk4027Isup3.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: QMOL (Gans & Shalloway, 2001), Mercury (Macrae et al., 2008) and ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012) and PLATON (Spek, 2009).

Ethyl 2,2-dimethyl-4-oxo-6-phenyl-2,3-dihydro-4H-pyran-5-carboxylate top

Crystal data top

C₁₆H₁₇ClO₄	D_x = 1.289 Mg m⁻³
M_r = 308.74	Melting point: 356 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.4412 (3) Å	Cell parameters from 3995 reflections
b = 7.6959 (2) Å	θ = 2.0–28.4°
c = 20.2651 (5) Å	µ = 0.25 mm⁻¹
β = 102.311 (2)°	T = 296 K
V = 1590.94 (7) Å³	Block, colourless
Z = 4	0.25 × 0.17 × 0.12 mm
F(000) = 648

Data collection top

Bruker Smart CCD Area-detector diffractometer	3995 independent reflections
Radiation source: fine-focus sealed tube	2978 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
phi and ω scans	θ_max = 28.4°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→13
T_min = 0.746, T_max = 0.845	k = −10→10
15125 measured reflections	l = −24→27

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0484P)² + 0.3683P] where P = (F_o² + 2F_c²)/3
3995 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.43713 (4)	0.28175 (7)	0.02231 (2)	0.06956 (16)
O1	0.76719 (10)	0.25784 (13)	0.33513 (5)	0.0475 (2)
O2	1.03226 (13)	0.63993 (19)	0.40015 (6)	0.0736 (4)
O3	0.96413 (11)	0.71077 (17)	0.24439 (7)	0.0670 (3)
O4	0.76146 (10)	0.76716 (13)	0.25811 (5)	0.0494 (3)
C1	0.56401 (14)	0.3304 (2)	0.22085 (7)	0.0476 (3)
H1	0.5298	0.3190	0.2594	0.057*
C2	0.48338 (14)	0.3058 (2)	0.15815 (7)	0.0515 (4)
H2	0.3950	0.2802	0.1541	0.062*
C3	0.53638 (14)	0.3198 (2)	0.10154 (7)	0.0451 (3)
C4	0.66627 (14)	0.3583 (2)	0.10654 (7)	0.0464 (3)
H4	0.7003	0.3669	0.0678	0.056*
C5	0.74647 (13)	0.38433 (18)	0.16963 (7)	0.0420 (3)
H5	0.8347	0.4102	0.1733	0.050*
C6	0.69542 (12)	0.37183 (17)	0.22726 (6)	0.0368 (3)
C7	0.78238 (12)	0.39149 (17)	0.29499 (6)	0.0374 (3)
C8	0.83024 (15)	0.2695 (2)	0.40731 (7)	0.0498 (4)
C9	0.96580 (15)	0.3470 (2)	0.41366 (7)	0.0524 (4)
H9A	1.0057	0.3629	0.4611	0.063*
H9B	1.0200	0.2667	0.3948	0.063*
C10	0.96159 (14)	0.5182 (2)	0.37801 (7)	0.0486 (3)
C11	0.86698 (12)	0.52417 (18)	0.31346 (6)	0.0391 (3)
C12	0.87223 (13)	0.67511 (18)	0.26829 (7)	0.0415 (3)
C13	0.75166 (17)	0.9164 (2)	0.21306 (9)	0.0601 (4)
H13A	0.8384	0.9637	0.2147	0.072*
H13B	0.6989	1.0060	0.2279	0.072*
C14	0.6913 (2)	0.8648 (3)	0.14272 (10)	0.0745 (5)
H14A	0.7470	0.7826	0.1269	0.112*
H14B	0.6805	0.9657	0.1142	0.112*
H14C	0.6072	0.8128	0.1416	0.112*
C15	0.74350 (17)	0.3815 (3)	0.44129 (8)	0.0685 (5)
H15A	0.7383	0.4966	0.4226	0.103*
H15B	0.7800	0.3869	0.4889	0.103*
H15C	0.6573	0.3319	0.4339	0.103*
C16	0.8362 (2)	0.0834 (3)	0.43209 (10)	0.0813 (6)
H16A	0.7490	0.0372	0.4255	0.122*
H16B	0.8768	0.0801	0.4793	0.122*
H16C	0.8866	0.0149	0.4072	0.122*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0693 (3)	0.0924 (4)	0.0396 (2)	−0.0122 (2)	−0.00473 (17)	−0.0057 (2)
O1	0.0577 (6)	0.0468 (6)	0.0350 (5)	−0.0092 (5)	0.0030 (4)	0.0070 (4)
O2	0.0762 (8)	0.0824 (9)	0.0531 (7)	−0.0320 (7)	−0.0067 (6)	−0.0001 (6)
O3	0.0486 (6)	0.0729 (8)	0.0846 (9)	−0.0020 (6)	0.0258 (6)	0.0254 (7)
O4	0.0498 (6)	0.0426 (5)	0.0581 (6)	0.0033 (4)	0.0169 (5)	0.0065 (5)
C1	0.0446 (7)	0.0631 (9)	0.0370 (7)	−0.0032 (6)	0.0127 (5)	0.0018 (6)
C2	0.0396 (7)	0.0701 (10)	0.0439 (7)	−0.0049 (7)	0.0067 (6)	0.0000 (7)
C3	0.0495 (7)	0.0482 (8)	0.0343 (6)	−0.0006 (6)	0.0015 (5)	−0.0007 (6)
C4	0.0531 (8)	0.0531 (8)	0.0347 (6)	−0.0021 (6)	0.0137 (6)	−0.0010 (6)
C5	0.0416 (7)	0.0468 (8)	0.0391 (7)	−0.0037 (6)	0.0120 (5)	−0.0007 (6)
C6	0.0403 (6)	0.0359 (6)	0.0338 (6)	−0.0003 (5)	0.0067 (5)	0.0016 (5)
C7	0.0396 (6)	0.0408 (7)	0.0326 (6)	0.0016 (5)	0.0095 (5)	0.0020 (5)
C8	0.0545 (8)	0.0584 (9)	0.0336 (7)	−0.0035 (7)	0.0025 (6)	0.0105 (6)
C9	0.0478 (8)	0.0663 (10)	0.0393 (7)	0.0017 (7)	0.0009 (6)	0.0076 (7)
C10	0.0435 (7)	0.0632 (9)	0.0377 (7)	−0.0068 (7)	0.0057 (6)	−0.0012 (6)
C11	0.0382 (6)	0.0442 (7)	0.0347 (6)	−0.0014 (5)	0.0075 (5)	0.0008 (5)
C12	0.0397 (7)	0.0428 (7)	0.0416 (7)	−0.0057 (6)	0.0079 (5)	−0.0018 (6)
C13	0.0657 (10)	0.0389 (8)	0.0749 (11)	0.0025 (7)	0.0134 (8)	0.0102 (8)
C14	0.0836 (13)	0.0675 (12)	0.0673 (11)	0.0038 (10)	0.0047 (10)	0.0165 (9)
C15	0.0616 (10)	0.1026 (15)	0.0442 (8)	0.0000 (10)	0.0179 (7)	0.0050 (9)
C16	0.0993 (15)	0.0726 (13)	0.0627 (11)	−0.0121 (11)	−0.0035 (10)	0.0308 (10)

Geometric parameters (Å, º) top

Cl1—C3	1.7401 (13)	C8—C9	1.516 (2)
O1—C7	1.3415 (16)	C8—C15	1.518 (2)
O1—C8	1.4732 (16)	C9—C10	1.498 (2)
O2—C10	1.2177 (19)	C9—H9A	0.9700
O3—C12	1.1954 (17)	C9—H9B	0.9700
O4—C12	1.3343 (17)	C10—C11	1.4622 (18)
O4—C13	1.4571 (18)	C11—C12	1.4871 (19)
C1—C2	1.3795 (19)	C13—C14	1.484 (3)
C1—C6	1.3876 (19)	C13—H13A	0.9700
C1—H1	0.9300	C13—H13B	0.9700
C2—C3	1.380 (2)	C14—H14A	0.9600
C2—H2	0.9300	C14—H14B	0.9600
C3—C4	1.371 (2)	C14—H14C	0.9600
C4—C5	1.3854 (18)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.3866 (18)	C15—H15C	0.9600
C5—H5	0.9300	C16—H16A	0.9600
C6—C7	1.4832 (16)	C16—H16B	0.9600
C7—C11	1.3498 (18)	C16—H16C	0.9600
C8—C16	1.515 (2)

C7—O1—C8	118.01 (11)	H9A—C9—H9B	107.9
C12—O4—C13	117.26 (11)	O2—C10—C11	123.09 (14)
C2—C1—C6	120.99 (12)	O2—C10—C9	123.08 (13)
C2—C1—H1	119.5	C11—C10—C9	113.82 (13)
C6—C1—H1	119.5	C7—C11—C10	120.09 (12)
C1—C2—C3	118.74 (13)	C7—C11—C12	121.88 (11)
C1—C2—H2	120.6	C10—C11—C12	117.96 (12)
C3—C2—H2	120.6	O3—C12—O4	124.04 (13)
C4—C3—C2	121.41 (13)	O3—C12—C11	124.53 (13)
C4—C3—Cl1	119.33 (11)	O4—C12—C11	111.43 (11)
C2—C3—Cl1	119.24 (11)	O4—C13—C14	110.47 (14)
C3—C4—C5	119.57 (12)	O4—C13—H13A	109.6
C3—C4—H4	120.2	C14—C13—H13A	109.6
C5—C4—H4	120.2	O4—C13—H13B	109.6
C4—C5—C6	120.13 (12)	C14—C13—H13B	109.6
C4—C5—H5	119.9	H13A—C13—H13B	108.1
C6—C5—H5	119.9	C13—C14—H14A	109.5
C5—C6—C1	119.15 (12)	C13—C14—H14B	109.5
C5—C6—C7	120.20 (11)	H14A—C14—H14B	109.5
C1—C6—C7	120.54 (11)	C13—C14—H14C	109.5
O1—C7—C11	124.54 (11)	H14A—C14—H14C	109.5
O1—C7—C6	110.78 (11)	H14B—C14—H14C	109.5
C11—C7—C6	124.68 (11)	C8—C15—H15A	109.5
O1—C8—C16	104.45 (13)	C8—C15—H15B	109.5
O1—C8—C9	108.65 (11)	H15A—C15—H15B	109.5
C16—C8—C9	111.84 (14)	C8—C15—H15C	109.5
O1—C8—C15	107.56 (12)	H15A—C15—H15C	109.5
C16—C8—C15	111.90 (15)	H15B—C15—H15C	109.5
C9—C8—C15	112.02 (14)	C8—C16—H16A	109.5
C10—C9—C8	111.96 (12)	C8—C16—H16B	109.5
C10—C9—H9A	109.2	H16A—C16—H16B	109.5
C8—C9—H9A	109.2	C8—C16—H16C	109.5
C10—C9—H9B	109.2	H16A—C16—H16C	109.5
C8—C9—H9B	109.2	H16B—C16—H16C	109.5

C6—C1—C2—C3	1.2 (2)	C16—C8—C9—C10	169.65 (14)
C1—C2—C3—C4	−0.4 (2)	C15—C8—C9—C10	−63.80 (16)
C1—C2—C3—Cl1	177.82 (13)	C8—C9—C10—O2	141.88 (16)
C2—C3—C4—C5	−0.2 (2)	C8—C9—C10—C11	−39.47 (18)
Cl1—C3—C4—C5	−178.35 (12)	O1—C7—C11—C10	7.7 (2)
C3—C4—C5—C6	−0.2 (2)	C6—C7—C11—C10	−171.07 (12)
C4—C5—C6—C1	1.0 (2)	O1—C7—C11—C12	−175.43 (12)
C4—C5—C6—C7	177.14 (13)	C6—C7—C11—C12	5.8 (2)
C2—C1—C6—C5	−1.6 (2)	O2—C10—C11—C7	−173.28 (15)
C2—C1—C6—C7	−177.69 (14)	C9—C10—C11—C7	8.07 (19)
C8—O1—C7—C11	10.50 (19)	O2—C10—C11—C12	9.8 (2)
C8—O1—C7—C6	−170.55 (11)	C9—C10—C11—C12	−168.88 (13)
C5—C6—C7—O1	−128.38 (13)	C13—O4—C12—O3	2.3 (2)
C1—C6—C7—O1	47.68 (17)	C13—O4—C12—C11	−178.24 (12)
C5—C6—C7—C11	50.56 (19)	C7—C11—C12—O3	−115.07 (17)
C1—C6—C7—C11	−133.37 (15)	C10—C11—C12—O3	61.8 (2)
C7—O1—C8—C16	−160.72 (14)	C7—C11—C12—O4	65.43 (17)
C7—O1—C8—C9	−41.22 (17)	C10—C11—C12—O4	−117.67 (13)
C7—O1—C8—C15	80.23 (16)	C12—O4—C13—C14	91.59 (17)
O1—C8—C9—C10	54.88 (17)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4ⁱ	0.93	2.66	3.3694 (18)	134
C15—H15B···O2ⁱⁱ	0.96	2.66	3.553 (2)	156
C13—H13B···Cgⁱⁱⁱ	0.97	2.96	3.6463 (17)	129

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

Acknowledgements

The authors thank Professor D. Velmurugan, Head of Department, CAS in Crystallography and Biophysics, TBI X-ray Facility, University of Madras, India, for his kind help with the data collection and Professor A. Ilangovan, School of Chemistry, Bharathidasan University, Tiruchirappalli, Tamilnadu, India, for fruitful discussions.

References

Bruker (2008). SMART, SAINT and SADABS . Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL- 6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gans, J. & Shalloway, D. (2001). J. Mol. Graphics Modell. 19, 557–559. Web of Science CrossRef CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sharmila, N., Sundar, T. V., Sakthivel, P. & Venkatesan, P. (2016). IUCrData, 1, x161924. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stewart, J. J. P. (2016). MOPAC2016. web: https://OpenMOPAC.net. Google Scholar
Suárez, M., Salfrán, E., Verdecia, Y., Ochoa, E., Alba, L., Martín, N., Martínez, R., Quinteiro, M., Seoane, C., Novoa, H., Blaton, N., Peeters, O. M. & De Ranter, C. (2002). Tetrahedron, 58, 953–960. Google Scholar
Vishnupriya, R., Suresh, J., Sivakumar, S., Kumar, R. R. & Lakshman, P. L. N. (2013). Acta Cryst. E69, o687–o688. CSD CrossRef IUCr Journals Google Scholar
Zhang, H.-Z., Kasibhatla, S., Kuemmerle, J., Kemnitzer, W., Ollis-Mason, K., Qiu, L., Crogan-Grundy, C., Tseng, B., Drewe, J. & Cai, S. X. (2005). J. Med. Chem. 48, 5215–5223. Web of Science CrossRef PubMed CAS Google Scholar
Zonouz, A. M., Moghani, D. & Okhravi, S. (2014). Curr. Chem. Lett. 3, 71–74. CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.