3-(3,4-Dimeth­oxy­benz­yl)chroman-4-one

Shalini, S.; Girija, C.R.; Simon, L.; Srinivasan, K.K.; Venkatesha, T.V.; Jotani, M.M.

doi:10.1107/S1600536813000925

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o241

doi:10.1107/S1600536813000925

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3-(3,4-Dimethoxybenzyl)chroman-4-one

S. Shalini,^a C. R. Girija,^a ^* Lalitha Simon,^c K. K. Srinivasan,^c T. V. Venkatesha ^d and M. M. Jotani ^e

^aChemistry Research Centre (affiliated to Kuvempu University), SSMRV Degree College, 4th T Block, Jayanagar, Bangalore 560 041, India, ^bDepartment of Chemistry, KMC International Center, Manipal University, Manipal 576 104, India, ^cDepartment of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal University, Manipal 576 104, India, ^dDepartment of Chemistry, Jnana Sahyadri, Kuvempu University, Shankargatta 577 451, India, and ^eDepartment of Physics, Bhavan's Sheth R. A. College of Science, Khanpur, Ahmedabad, Gujarat 380 001, India
^*Correspondence e-mail: girija.shivakumar@rediffmail.com

(Received 25 November 2012; accepted 10 January 2013; online 16 January 2013)

In the title compound, C₁₈H₁₈O₄, the six-membered chroman-4-one ring adopts an envelope conformation with the C atom bonded to the bridging CH₂ atom as the flap. The dihedral angle between the mean plane of the fused pyranone ring and the dimethoxy-substituted benzene ring is 89.72 (2)°. In the crystal, adjacent molecules are linked via C—H⋯π interactions.

Related literature

For the biological activity and pharmaceutical properties of chromenes(benzopyrans) and a similar structure, see: Jasinski et al. (2010 ). For bond-length data see: Allen et al. (1987 ). For ring conformations, see: Cremer & Pople (1975 )

Experimental

Crystal data

C₁₈H₁₈O₄
M_r = 298.33
Monoclinic, C 2/c
a = 30.414 (4) Å
b = 5.453 (3) Å
c = 20.661 (5) Å
β = 118.568 (3)°
V = 3009.4 (19) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.954, T_max = 0.991
13379 measured reflections
2802 independent reflections
1955 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.142
S = 1.03
2802 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯Cgⁱ	0.96	2.87	3.755 (4)	154
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 2012 ) and CAMERON (Watkin et al., 1993 ); software used to prepare material for publication: PARST (Nardelli, 1995 ) and WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813000925/hg5275sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813000925/hg5275Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813000925/hg5275Isup3.cml

checkCIF report

Comment top

Homoisoflavonones have wide spectrum of biological activity. In the past decades they are widely used as antifungal, antiviral, antimutagenic,antiproliferative, antioxidant, and protein tyrosine kinase (PTK) inhibitor activities (Jasinski et al., 2010). Because of their wide range of pharmacological activity, the title compound (I) was synthesized and the crystal structure determined.

The bond distances and angles are found to have normal values (Allen et al., 1987). The pyranone ring has adopted the envelope conformation (Cremer & Pople, 1975) as shown in Fig.1. The ring puckering parameters q₂ = 0.3696 (2) Å,q₃=0.2785 (3) Å, Q_T = 0.4628 Å, and ϕ = 276.96 (2)°, are indicative of an envelope conformation. The carbonyl ketone, being an electron-withdrawing group, makes the internal aromatic angle 118.17 (3)° at the C9 atom. The electronegative oxygen of the fused pyranone ring shows no change in the internal aromatic angle at the C5 atom. The six membered fused pyranone ring makes a dihedral angle of 89.72 (2)° with the dimethoxy substituted phenyl ring.

No classical inter- or intra-molecular hydrogen bonds are observed. The packing of the title compound is stabilized into a three-dimensional network by C—H···π intermolecular interactions, which serve to link inversion-related sheets (Fig 2).

Related literature top

For the biological activity and pharmaceutical properties of chromenes(benzopyrans) and a similar structure, see: Jasinski et al. (2010). For bond-length data see: Allen et al. (1987); For ring conformations, see: Cremer & Pople (1975)

Experimental top

2'-Hydroxydihydrochalcone (0.1 g) was dissolved in ethanol (10 ml) and refluxed with paraformaldehyde (0.022 g) and 50% aqueous diethylamine (0.2 ml) for 7 hrs. Ethanol was distilled off and the residue was taken up in ethyl acetate. The ethyl acetate layer washed with water then with dilute HCl and finally with water. Ethyl acetate was distilled off and the oily residue was column chromatographed over silica using pet ether(7): ethyl acetate(3) as eluent to get the 3-(3,4-dimethoxybenzyl)-2,3-dihydro-4H-chroman-4-one. Single crystals of the title compound were grown using methanol as solvent by slow evaporation technique and white needle-like crystals were harvested at room temperature. M.P. 397 K. Yield: 65%. IR(KBr):3001,2947,1689 cm^-1. ¹H-NMR,(400 MHz, DMSO) 4.3(dd,J=11.2,4.4Hz,1H,2-H), 4.2(dd,J=11.6, 9.2Hz,1H,2-H), 2.6(m,1H,3-H), 3.1(m,2H,9 -H), 3.7[S,6H,3 ,4 (2x OCH3)], 7.7(dd,J=8.1, 0.6Hz,1H, Ar-H), 7.5(m, 1H,Ar-H), 6.7(dd,J=8.4 ,2Hz,1H,Ar-H).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PARST (Nardelli, 1995) and WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labeling scheme with displacement ellipsoids drawn at 50% probability level.
	Fig. 2. Packing diagram of (I) Dashed lines indicate C – H···π interactions. H-atoms not involving in H-bonding are omitted for clarity.

3-(3,4-Dimethoxybenzyl)chroman-4-one top

Crystal data top

C₁₈H₁₈O₄	F(000) = 1264
M_r = 298.33	D_x = 1.317 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 575 reflections
a = 30.414 (4) Å	θ = 2.0–25.0°
b = 5.453 (3) Å	µ = 0.09 mm⁻¹
c = 20.661 (5) Å	T = 295 K
β = 118.568 (3)°	Block, colourless
V = 3009.4 (19) Å³	0.30 × 0.20 × 0.20 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD diffractometer	2802 independent reflections
Radiation source: fine-focus sealed tube	1955 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω and ϕ scan	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −36→34
T_min = 0.954, T_max = 0.991	k = −6→6
13379 measured reflections	l = −13→25

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0617P)² + 1.6626P] where P = (F_o² + 2F_c²)/3
2802 reflections	(Δ/σ)_max < 0.001
201 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₈H₁₈O₄	V = 3009.4 (19) Å³
M_r = 298.33	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 30.414 (4) Å	µ = 0.09 mm⁻¹
b = 5.453 (3) Å	T = 295 K
c = 20.661 (5) Å	0.30 × 0.20 × 0.20 mm
β = 118.568 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2802 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1955 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.991	R_int = 0.031
13379 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
2802 reflections	Δρ_min = −0.14 e Å⁻³
201 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
O1	0.29295 (5)	−0.2335 (3)	0.08927 (7)	0.0703 (4)
O2	0.32093 (6)	0.1349 (3)	0.27652 (7)	0.0795 (5)
O3	0.03885 (6)	0.2688 (3)	−0.10089 (8)	0.0857 (5)
O4	0.05593 (6)	−0.0630 (3)	−0.00297 (9)	0.0828 (5)
C1	0.26773 (8)	−0.0139 (4)	0.08851 (10)	0.0695 (6)
H1A	0.2353	−0.0109	0.0445	0.083*
H1B	0.2869	0.125	0.0862	0.083*
C2	0.26030 (7)	0.0125 (4)	0.15473 (10)	0.0591 (5)
H2	0.2423	−0.1338	0.1569	0.071*
C3	0.31104 (7)	0.0101 (4)	0.22267 (10)	0.0576 (5)
C4	0.34695 (7)	−0.1611 (4)	0.21878 (10)	0.0558 (5)
C5	0.39185 (8)	−0.2207 (4)	0.28105 (12)	0.0743 (6)
H5	0.4002	−0.1446	0.3257	0.089*
C6	0.42394 (9)	−0.3901 (5)	0.27737 (16)	0.0874 (8)
H6	0.4537	−0.4293	0.3193	0.105*
C7	0.41172 (10)	−0.5014 (5)	0.21116 (17)	0.0926 (8)
H7	0.4336	−0.6151	0.2085	0.111*
C8	0.36811 (9)	−0.4479 (4)	0.14941 (15)	0.0809 (7)
H8	0.3602	−0.5257	0.1051	0.097*
C9	0.33563 (8)	−0.2773 (4)	0.15279 (11)	0.0598 (5)
C10	0.22947 (8)	0.2319 (4)	0.15249 (12)	0.0725 (6)
H10A	0.2481	0.3796	0.1555	0.087*
H10B	0.2245	0.2278	0.1955	0.087*
C11	0.17901 (7)	0.2453 (4)	0.08429 (11)	0.0604 (5)
C12	0.16944 (8)	0.4179 (4)	0.03117 (12)	0.0681 (6)
H12	0.1945	0.5279	0.0371	0.082*
C13	0.12308 (9)	0.4315 (4)	−0.03128 (12)	0.0692 (6)
H13	0.1172	0.5511	−0.0666	0.083*
C14	0.08591 (8)	0.2697 (4)	−0.04133 (11)	0.0626 (5)
C15	0.09518 (7)	0.0896 (4)	0.01179 (11)	0.0602 (5)
C16	0.14145 (7)	0.0798 (4)	0.07368 (11)	0.0608 (5)
H16	0.1477	−0.04	0.1091	0.073*
C17	0.02452 (12)	0.4796 (6)	−0.14567 (14)	0.1180 (11)
H17A	0.0302	0.6225	−0.1155	0.177*
H17B	−0.0103	0.4689	−0.1811	0.177*
H17C	0.044	0.4912	−0.1709	0.177*
C18	0.06175 (10)	−0.2336 (5)	0.05250 (14)	0.0907 (8)
H18A	0.0881	−0.3467	0.0606	0.136*
H18B	0.031	−0.322	0.037	0.136*
H18C	0.0701	−0.1475	0.0974	0.136*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0715 (9)	0.0778 (10)	0.0596 (8)	0.0033 (8)	0.0297 (7)	−0.0169 (7)
O2	0.0778 (10)	0.0985 (12)	0.0547 (8)	−0.0048 (9)	0.0257 (7)	−0.0235 (8)
O3	0.0705 (10)	0.1063 (13)	0.0663 (9)	0.0163 (9)	0.0214 (8)	0.0078 (9)
O4	0.0645 (10)	0.0931 (12)	0.0908 (11)	−0.0091 (8)	0.0372 (8)	0.0017 (9)
C1	0.0716 (14)	0.0771 (14)	0.0552 (12)	0.0045 (11)	0.0266 (10)	−0.0073 (10)
C2	0.0586 (12)	0.0636 (12)	0.0540 (11)	−0.0042 (9)	0.0259 (9)	−0.0108 (9)
C3	0.0601 (12)	0.0652 (12)	0.0491 (10)	−0.0107 (9)	0.0275 (9)	−0.0071 (9)
C4	0.0520 (11)	0.0580 (11)	0.0575 (11)	−0.0085 (9)	0.0262 (9)	0.0008 (9)
C5	0.0647 (14)	0.0821 (15)	0.0700 (13)	−0.0081 (12)	0.0272 (11)	0.0052 (11)
C6	0.0614 (14)	0.0860 (17)	0.1025 (19)	0.0083 (13)	0.0293 (13)	0.0242 (15)
C7	0.0870 (18)	0.0789 (17)	0.120 (2)	0.0132 (14)	0.0564 (17)	0.0066 (16)
C8	0.0863 (17)	0.0707 (15)	0.0970 (17)	0.0048 (13)	0.0530 (15)	−0.0066 (13)
C9	0.0632 (12)	0.0564 (11)	0.0660 (12)	−0.0073 (9)	0.0359 (10)	−0.0035 (9)
C10	0.0687 (14)	0.0697 (14)	0.0707 (13)	0.0027 (11)	0.0264 (11)	−0.0177 (11)
C11	0.0624 (12)	0.0570 (12)	0.0642 (12)	0.0038 (10)	0.0321 (10)	−0.0080 (10)
C12	0.0704 (14)	0.0621 (13)	0.0795 (14)	−0.0028 (10)	0.0419 (12)	−0.0047 (11)
C13	0.0846 (16)	0.0658 (13)	0.0666 (13)	0.0117 (12)	0.0438 (12)	0.0099 (10)
C14	0.0615 (12)	0.0734 (14)	0.0552 (11)	0.0108 (11)	0.0297 (10)	−0.0025 (10)
C15	0.0589 (12)	0.0649 (12)	0.0665 (12)	0.0031 (10)	0.0378 (10)	−0.0032 (10)
C16	0.0662 (13)	0.0614 (12)	0.0594 (11)	0.0086 (10)	0.0338 (10)	0.0024 (9)
C17	0.128 (2)	0.112 (2)	0.0697 (16)	0.0409 (19)	0.0112 (15)	0.0049 (16)
C18	0.1060 (19)	0.0895 (18)	0.1038 (18)	−0.0211 (15)	0.0720 (16)	−0.0050 (15)

Geometric parameters (Å, º) top

O1—C9	1.355 (2)	C7—H7	0.93
O1—C1	1.418 (3)	C8—C9	1.383 (3)
O2—C3	1.213 (2)	C8—H8	0.93
O3—C14	1.371 (2)	C10—C11	1.509 (3)
O3—C17	1.408 (3)	C10—H10A	0.97
O4—C15	1.365 (2)	C10—H10B	0.97
O4—C18	1.420 (3)	C11—C12	1.368 (3)
C1—C2	1.496 (3)	C11—C16	1.388 (3)
C1—H1A	0.97	C12—C13	1.385 (3)
C1—H1B	0.97	C12—H12	0.93
C2—C10	1.507 (3)	C13—C14	1.369 (3)
C2—C3	1.510 (3)	C13—H13	0.93
C2—H2	0.98	C14—C15	1.397 (3)
C3—C4	1.468 (3)	C15—C16	1.377 (3)
C4—C9	1.389 (3)	C16—H16	0.93
C4—C5	1.395 (3)	C17—H17A	0.96
C5—C6	1.372 (3)	C17—H17B	0.96
C5—H5	0.93	C17—H17C	0.96
C6—C7	1.375 (4)	C18—H18A	0.96
C6—H6	0.93	C18—H18B	0.96
C7—C8	1.362 (3)	C18—H18C	0.96

C9—O1—C1	114.98 (15)	C2—C10—C11	114.02 (16)
C14—O3—C17	116.7 (2)	C2—C10—H10A	108.7
C15—O4—C18	117.46 (17)	C11—C10—H10A	108.7
O1—C1—C2	112.85 (17)	C2—C10—H10B	108.7
O1—C1—H1A	109	C11—C10—H10B	108.7
C2—C1—H1A	109	H10A—C10—H10B	107.6
O1—C1—H1B	109	C12—C11—C16	118.52 (19)
C2—C1—H1B	109	C12—C11—C10	120.9 (2)
H1A—C1—H1B	107.8	C16—C11—C10	120.57 (19)
C10—C2—C3	112.31 (16)	C11—C12—C13	121.0 (2)
C10—C2—C1	114.33 (18)	C11—C12—H12	119.5
C3—C2—C1	108.37 (16)	C13—C12—H12	119.5
C10—C2—H2	107.2	C14—C13—C12	120.4 (2)
C3—C2—H2	107.2	C14—C13—H13	119.8
C1—C2—H2	107.2	C12—C13—H13	119.8
O2—C3—C4	122.84 (18)	C13—C14—C15	119.46 (19)
O2—C3—C2	122.88 (19)	C13—C14—O3	124.8 (2)
C4—C3—C2	114.26 (16)	C15—C14—O3	115.75 (19)
C9—C4—C5	118.2 (2)	O4—C15—C16	125.46 (19)
C9—C4—C3	120.14 (17)	O4—C15—C14	115.26 (18)
C5—C4—C3	121.58 (18)	C16—C15—C14	119.28 (19)
C6—C5—C4	121.0 (2)	C15—C16—C11	121.32 (19)
C6—C5—H5	119.5	C15—C16—H16	119.3
C4—C5—H5	119.5	C11—C16—H16	119.3
C5—C6—C7	119.4 (2)	O3—C17—H17A	109.5
C5—C6—H6	120.3	O3—C17—H17B	109.5
C7—C6—H6	120.3	H17A—C17—H17B	109.5
C8—C7—C6	121.1 (2)	O3—C17—H17C	109.5
C8—C7—H7	119.5	H17A—C17—H17C	109.5
C6—C7—H7	119.5	H17B—C17—H17C	109.5
C7—C8—C9	119.7 (2)	O4—C18—H18A	109.5
C7—C8—H8	120.1	O4—C18—H18B	109.5
C9—C8—H8	120.1	H18A—C18—H18B	109.5
O1—C9—C8	116.51 (19)	O4—C18—H18C	109.5
O1—C9—C4	122.91 (18)	H18A—C18—H18C	109.5
C8—C9—C4	120.6 (2)	H18B—C18—H18C	109.5

C9—O1—C1—C2	−49.8 (2)	C3—C4—C9—C8	−176.84 (19)
O1—C1—C2—C10	−174.62 (16)	C3—C2—C10—C11	178.29 (17)
O1—C1—C2—C3	59.3 (2)	C1—C2—C10—C11	54.3 (3)
C10—C2—C3—O2	16.4 (3)	C2—C10—C11—C12	−108.8 (2)
C1—C2—C3—O2	143.6 (2)	C2—C10—C11—C16	70.3 (3)
C10—C2—C3—C4	−165.23 (17)	C16—C11—C12—C13	1.3 (3)
C1—C2—C3—C4	−38.0 (2)	C10—C11—C12—C13	−179.64 (19)
O2—C3—C4—C9	−172.37 (19)	C11—C12—C13—C14	−0.6 (3)
C2—C3—C4—C9	9.2 (3)	C12—C13—C14—C15	−0.4 (3)
O2—C3—C4—C5	10.7 (3)	C12—C13—C14—O3	179.69 (18)
C2—C3—C4—C5	−167.68 (18)	C17—O3—C14—C13	−14.9 (3)
C9—C4—C5—C6	−0.2 (3)	C17—O3—C14—C15	165.1 (2)
C3—C4—C5—C6	176.79 (19)	C18—O4—C15—C16	5.3 (3)
C4—C5—C6—C7	0.4 (4)	C18—O4—C15—C14	−174.00 (18)
C5—C6—C7—C8	−0.6 (4)	C13—C14—C15—O4	179.99 (18)
C6—C7—C8—C9	0.6 (4)	O3—C14—C15—O4	0.0 (3)
C1—O1—C9—C8	−162.74 (19)	C13—C14—C15—C16	0.7 (3)
C1—O1—C9—C4	17.7 (3)	O3—C14—C15—C16	−179.39 (17)
C7—C8—C9—O1	−179.9 (2)	O4—C15—C16—C11	−179.27 (18)
C7—C8—C9—C4	−0.4 (3)	C14—C15—C16—C11	0.0 (3)
C5—C4—C9—O1	179.68 (18)	C12—C11—C16—C15	−0.9 (3)
C3—C4—C9—O1	2.7 (3)	C10—C11—C16—C15	179.95 (18)
C5—C4—C9—C8	0.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cgⁱ	0.96	2.87	3.755 (4)	154

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈O₄
M_r	298.33
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	30.414 (4), 5.453 (3), 20.661 (5)
β (°)	118.568 (3)
V (Å³)	3009.4 (19)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.954, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	13379, 2802, 1955
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.142, 1.03
No. of reflections	2802
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.14

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and CAMERON (Watkin et al., 1993), PARST (Nardelli, 1995) and WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cgⁱ	0.96	2.87	3.755 (4)	154

Symmetry code: (i) x, y−1, z.

Acknowledgements

The authors thank Dr Babu Varghese, Scientific Officer, Sophisticated Analytical Instrument Facility (SAIF), Indian Institute of Technology (IIT), Chennai, India, for the data collection. SS and CRG also thank the Rashtriya Sikshana Samithi Trust (RSST) and the Principal, Sri Shivananda Memorial Rashtriya Vidyalaya (SSMRV) Degree College, Bangalore, for their constant support and encouragement in carrying out this work.

References

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