(7-Chloro-2-oxo-2H-chromen-4-yl)methyl di­ethyl­carbamodi­thio­ate

Meenakshi, T.G.; Shylajakumari, J.; Devarajegowda, H.C.; Kumar, K.M.; Kotresh, O.

doi:10.1107/S160053681302240X

organic compounds

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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Pages o1431-o1432

doi:10.1107/S160053681302240X

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(7-Chloro-2-oxo-2H-chromen-4-yl)methyl diethylcarbamodithioate

T. G. Meenakshi,^a J. Shylajakumari,^b H. C. Devarajegowda,^c ^* K. Mahesh Kumar ^d and O. Kotresh ^d

^aDepartment of Physics, Y. Y. D. Govt. First Grade College, Belur 573 115, Hassan, Karnataka, India, ^bDepartment of Physics, AVK College for Women, Hassan 573 201, Karnataka, India, ^cDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, and ^dDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580 001, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 31 July 2013; accepted 9 August 2013; online 14 August 2013)

In the title compound, C₁₅H₁₆ClNO₂S₂, the 2H-chromene ring system is nearly planar, with a maximum deviation of 0.023 (2) Å. In the crystal, C—H⋯O hydrogen bonds give R₂¹(7) motifs, which generate [100] chains. C—H⋯π and π–π interactions between chromene moieties [shortest ring centroid–centroid distance = 3.6199 (13) Å] consolidate the packing.

Related literature

For biological applications of coumarins and dithiocarbamates, see: Abd Elhafez et al. (2003 ); Basanagouda et al. (2009 ); Borges et al. (2009 ); Bottomeley et al. (1985 ); Emmanuel-Giota et al. (2001 ); Hamdi & Dixneuf (2007 ); Marchenko et al. (2006 ); Teramoto et al. (1980 ); Trapkov et al. (1996 ). For a related structure and the synthesis of the title compound, see: Kumar et al. (2012 ).

Experimental

Crystal data

C₁₅H₁₆ClNO₂S₂
M_r = 341.86
Monoclinic, P 2₁ /c
a = 7.7005 (2) Å
b = 23.3452 (8) Å
c = 9.7016 (3) Å
β = 110.349 (2)°
V = 1635.21 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 296 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.770, T_max = 1.000
11261 measured reflections
2865 independent reflections
2413 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.091
S = 1.08
2865 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C14/C15/C18–C21 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O5ⁱ	0.97	2.43	3.264 (3)	144
C18—H18⋯O5ⁱ	0.93	2.54	3.424 (3)	159
C8—H8A⋯Cg2ⁱⁱ	0.97	2.95	3.792 (3)	146
Symmetry codes: (i) x+1, y, z; (ii) x, y, z-1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681302240X/zs2274sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681302240X/zs2274Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681302240X/zs2274Isup3.cml

checkCIF report

Comment top

Coumarins are a large family of compounds, of natural and synthetic origin, that display a variety of pharmacological properties. Due to their structural variability they occupy an important place in the realm of natural products and synthetic organic chemistry. Recent studies pay special attention to their antioxidative and enzymatic inhibition properties (Borges et al., 2009). Numerous functionalized coumarins have been presented as anti-bacterial (Abd Elhafez et al., 2003; Basanagouda et al., 2009), anti-oxidant (Trapkov et al., 1996), anti-inflammatory (Emmanuel-Giota et al., 2001; Hamdi & Dixneuf, 2007), anti-coagulant (Hamdi & Dixneuf, 2007) and anti-tumour (Marchenko et al., 2006) agents.

Antifungal treatments are widely used to prevent the development of pathogenic fungi, which are responsible each year for various crop diseases leading to large economical losses. The dithiocarbamate fungicides form the most important class of pesticides for broad spectrum control of a variety of fungal diseases on seeds, fruits and vegetables. Among dithiocarbamates, ethylenebis (dithiocarbamates) are the most widely used fungicides in the world. Due to their non selectivity and multisite action they are still spread in large quantities in association with more specific pesticides. Despite their low acute toxicity, these fungicides constitute a pesticide family of environmental concern since many reports suspect them of inducing neurological troubles resembling Parkinson disease, carcinogenesis w and teratogenesis (Teramoto et al., 1980; Bottomeley et al., 1985). Therefore, the synthesis of new coumarin derivatives is of considerable interest. In order to study the influence of new substituents on the activity of the coumarin dithiocarbamates (Kumar et al., 2012), the title compound, (7-chloro-2-oxo-2H-chromen-4-yl)methyl diethylcarbamodithioate, C₁₅H₁₆Cl N O₂S₂, has been synthesized and the structure is reported herein.

In this compound (Fig. 1), the 2H-chromene ring system is nearly planar, with a maximum deviation of 0.023 (2) Å. In the crystal, cyclic intermolecular C12—H12A···O5ⁱ and C18—H18···O5ⁱ hydrogen-bonding interactions (Table 1) through an R¹₂(7) ring motif, generate chains which extend along the a axis. In addition, C—H···π and π–π interactions involving the benzene ring of the chromene moiety defined by C14/C15/C18—C21) [shortest centroid–centroid distance = 3.6199 (13) Å] stabilize the crystal packing and give a two-dimensional layered structure lying along [0 1 0] (Fig. 2).

Related literature top

For biological applications of coumarins and dithiocarbamates, see: Abd Elhafez et al. (2003); Basanagouda et al. (2009); Borges et al. (2009); Bottomeley et al. (1985); Emmanuel-Giota et al. (2001); Hamdi & Dixneuf (2007); Marchenko et al. (2006); Teramoto et al. (1980); Trapkov et al. (1996). For a related structure and the synthesis of the title compound, see: Kumar et al. (2012).

Experimental top

All the chemicals used were of analytical reagent grade and were used directly without further purification. The title compound was synthesized according to the reported method (Kumar et al., 2012). The compound was recrystallized from an ethanol-chloroform mixture giving colourless crystals (m.p. 383–385 K: yield, 88%).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. A perspective view of the packing of the molecules in the unit cell, with hydrogen bonds shown as dashed lines.

(7-Chloro-2-oxo-2H-chromen-4-yl)methyl diethylcarbamodithioate top

Crystal data top

C₁₅H₁₆ClNO₂S₂	F(000) = 712
M_r = 341.86	D_x = 1.389 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 383–385 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.7005 (2) Å	Cell parameters from 2865 reflections
b = 23.3452 (8) Å	θ = 1.7–25.0°
c = 9.7016 (3) Å	µ = 0.49 mm⁻¹
β = 110.349 (2)°	T = 296 K
V = 1635.21 (9) Å³	Plate, colourless
Z = 4	0.24 × 0.20 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2865 independent reflections
Radiation source: fine-focus sealed tube	2413 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −9→9
T_min = 0.770, T_max = 1.000	k = −26→27
11261 measured reflections	l = −10→11

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0317P)² + 1.0627P] where P = (F_o² + 2F_c²)/3
2865 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₅H₁₆ClNO₂S₂	V = 1635.21 (9) Å³
M_r = 341.86	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7005 (2) Å	µ = 0.49 mm⁻¹
b = 23.3452 (8) Å	T = 296 K
c = 9.7016 (3) Å	0.24 × 0.20 × 0.12 mm
β = 110.349 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2865 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2413 reflections with I > 2σ(I)
T_min = 0.770, T_max = 1.000	R_int = 0.024
11261 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.08	Δρ_max = 0.38 e Å⁻³
2865 reflections	Δρ_min = −0.28 e Å⁻³
190 parameters

Special details top

Experimental. IR (KBr): 675 cm^-1 (C—S), 1270 cm^-1 (C=S), 1087 cm^-1 (C—O), 856 cm^-1 (C—N),1202 cm^-1 (C—O—C), 1721 cm^-1 (C=O). GCMS: m/e: 341. 1H NMR (400 MHz, CDCl₃, \?,. p.p.m): 1.25–1.27 (m, 2H), 1.29–1.32(m, 2H, C₁), 3.73–3.79 (m, 6H, C₁₇), 4.04 (m, 2H, C₄), 6.56 (s,1H, C₁₄), 7.29 (m,1H, C₁₅), 7.34 (s,1H, C₈), 7.70(d, 1H). Mol. Formula: C₁₅H₁₆ClNO₂S₂. Elemental analysis for C₁₅H₁₆ClNO₂S₂: C, 52.65; H, 4.67; N, 4.03.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl1	0.57033 (9)	0.42546 (3)	1.32189 (7)	0.0585 (2)
S2	0.39037 (8)	0.35206 (3)	0.57232 (6)	0.04076 (17)
S3	0.03698 (10)	0.35303 (3)	0.30671 (8)	0.0604 (2)
O4	0.01217 (19)	0.44543 (7)	0.86479 (16)	0.0419 (4)
O5	−0.2474 (2)	0.45502 (9)	0.6779 (2)	0.0622 (5)
N6	0.2357 (3)	0.26131 (9)	0.4244 (2)	0.0508 (5)
C7	0.5614 (4)	0.22830 (15)	0.4920 (4)	0.0815 (10)
H7A	0.6573	0.2077	0.5657	0.122*
H7B	0.6027	0.2666	0.4850	0.122*
H7C	0.5334	0.2094	0.3989	0.122*
C8	0.3895 (4)	0.23021 (12)	0.5337 (3)	0.0658 (8)
H8A	0.3502	0.1914	0.5429	0.079*
H8B	0.4192	0.2487	0.6286	0.079*
C9	0.1075 (4)	0.22566 (13)	0.3077 (3)	0.0656 (8)
H9A	0.1741	0.1929	0.2895	0.079*
H9B	0.0612	0.2478	0.2176	0.079*
C10	−0.0528 (5)	0.20496 (15)	0.3481 (5)	0.0893 (11)
H10A	−0.1327	0.1819	0.2697	0.134*
H10B	−0.1207	0.2372	0.3640	0.134*
H10C	−0.0076	0.1825	0.4363	0.134*
C11	0.2113 (3)	0.31763 (11)	0.4273 (3)	0.0411 (6)
C12	0.3112 (3)	0.42508 (9)	0.5676 (2)	0.0357 (5)
H12A	0.4168	0.4508	0.5943	0.043*
H12B	0.2311	0.4345	0.4685	0.043*
C13	0.2076 (3)	0.43346 (9)	0.6713 (2)	0.0321 (5)
C14	0.3045 (3)	0.43248 (9)	0.8290 (2)	0.0315 (5)
C15	0.2014 (3)	0.43771 (9)	0.9211 (2)	0.0335 (5)
C16	−0.0825 (3)	0.44760 (11)	0.7160 (3)	0.0410 (6)
C17	0.0229 (3)	0.44064 (10)	0.6207 (2)	0.0380 (5)
H17	−0.0394	0.4411	0.5196	0.046*
C18	0.4971 (3)	0.42649 (10)	0.8967 (2)	0.0365 (5)
H18	0.5709	0.4239	0.8387	0.044*
C19	0.5781 (3)	0.42443 (10)	1.0466 (2)	0.0392 (5)
H19	0.7057	0.4203	1.0902	0.047*
C20	0.4683 (3)	0.42857 (10)	1.1319 (2)	0.0384 (5)
C21	0.2794 (3)	0.43545 (10)	1.0716 (2)	0.0384 (5)
H21	0.2070	0.4385	1.1306	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0491 (4)	0.0892 (5)	0.0311 (3)	0.0021 (3)	0.0063 (3)	0.0033 (3)
S2	0.0367 (3)	0.0470 (4)	0.0369 (3)	0.0075 (3)	0.0107 (2)	−0.0014 (3)
S3	0.0507 (4)	0.0590 (4)	0.0541 (4)	0.0072 (3)	−0.0036 (3)	−0.0032 (3)
O4	0.0246 (7)	0.0666 (11)	0.0366 (9)	0.0023 (7)	0.0134 (7)	−0.0014 (8)
O5	0.0249 (8)	0.1095 (16)	0.0517 (11)	0.0071 (9)	0.0127 (8)	0.0029 (11)
N6	0.0462 (12)	0.0463 (13)	0.0573 (13)	0.0041 (10)	0.0150 (10)	−0.0056 (10)
C7	0.0573 (18)	0.078 (2)	0.100 (3)	0.0199 (16)	0.0165 (18)	−0.0167 (19)
C8	0.0703 (19)	0.0452 (16)	0.072 (2)	0.0111 (14)	0.0122 (16)	0.0004 (14)
C9	0.0649 (18)	0.0548 (17)	0.072 (2)	0.0003 (14)	0.0170 (16)	−0.0194 (15)
C10	0.067 (2)	0.076 (2)	0.120 (3)	−0.0166 (18)	0.027 (2)	−0.013 (2)
C11	0.0386 (12)	0.0494 (15)	0.0384 (13)	0.0022 (11)	0.0174 (11)	−0.0026 (11)
C12	0.0339 (11)	0.0416 (13)	0.0342 (12)	0.0008 (10)	0.0151 (10)	0.0022 (10)
C13	0.0325 (11)	0.0311 (11)	0.0346 (11)	−0.0011 (9)	0.0142 (9)	0.0001 (9)
C14	0.0279 (10)	0.0341 (12)	0.0326 (11)	−0.0010 (9)	0.0109 (9)	−0.0009 (9)
C15	0.0271 (10)	0.0389 (12)	0.0356 (12)	−0.0014 (9)	0.0121 (9)	−0.0009 (9)
C16	0.0274 (11)	0.0551 (15)	0.0398 (13)	0.0016 (10)	0.0107 (10)	0.0006 (11)
C17	0.0317 (11)	0.0497 (14)	0.0320 (12)	0.0021 (10)	0.0104 (9)	0.0018 (10)
C18	0.0292 (11)	0.0447 (13)	0.0380 (12)	0.0007 (9)	0.0145 (10)	−0.0008 (10)
C19	0.0281 (11)	0.0475 (14)	0.0388 (13)	0.0011 (10)	0.0077 (10)	0.0012 (11)
C20	0.0389 (12)	0.0424 (13)	0.0321 (12)	−0.0016 (10)	0.0102 (10)	0.0011 (10)
C21	0.0379 (12)	0.0470 (14)	0.0349 (12)	0.0001 (10)	0.0185 (10)	−0.0018 (10)

Geometric parameters (Å, º) top

Cl1—C20	1.735 (2)	C10—H10A	0.9600
S2—C11	1.783 (2)	C10—H10B	0.9600
S2—C12	1.806 (2)	C10—H10C	0.9600
S3—C11	1.662 (2)	C12—C13	1.498 (3)
O4—C16	1.373 (3)	C12—H12A	0.9700
O4—C15	1.379 (2)	C12—H12B	0.9700
O5—C16	1.205 (3)	C13—C17	1.344 (3)
N6—C11	1.330 (3)	C13—C14	1.451 (3)
N6—C9	1.474 (3)	C14—C15	1.392 (3)
N6—C8	1.477 (3)	C14—C18	1.404 (3)
C7—C8	1.513 (4)	C15—C21	1.373 (3)
C7—H7A	0.9600	C16—C17	1.437 (3)
C7—H7B	0.9600	C17—H17	0.9300
C7—H7C	0.9600	C18—C19	1.370 (3)
C8—H8A	0.9700	C18—H18	0.9300
C8—H8B	0.9700	C19—C20	1.378 (3)
C9—C10	1.498 (5)	C19—H19	0.9300
C9—H9A	0.9700	C20—C21	1.375 (3)
C9—H9B	0.9700	C21—H21	0.9300

C11—S2—C12	104.12 (11)	C13—C12—H12A	109.4
C16—O4—C15	121.54 (17)	S2—C12—H12A	109.4
C11—N6—C9	120.8 (2)	C13—C12—H12B	109.4
C11—N6—C8	123.7 (2)	S2—C12—H12B	109.4
C9—N6—C8	115.4 (2)	H12A—C12—H12B	108.0
C8—C7—H7A	109.5	C17—C13—C14	118.6 (2)
C8—C7—H7B	109.5	C17—C13—C12	120.9 (2)
H7A—C7—H7B	109.5	C14—C13—C12	120.47 (18)
C8—C7—H7C	109.5	C15—C14—C18	117.00 (19)
H7A—C7—H7C	109.5	C15—C14—C13	118.45 (18)
H7B—C7—H7C	109.5	C18—C14—C13	124.5 (2)
N6—C8—C7	112.4 (3)	C21—C15—O4	115.93 (19)
N6—C8—H8A	109.1	C21—C15—C14	122.90 (19)
C7—C8—H8A	109.1	O4—C15—C14	121.17 (19)
N6—C8—H8B	109.1	O5—C16—O4	116.5 (2)
C7—C8—H8B	109.1	O5—C16—C17	126.2 (2)
H8A—C8—H8B	107.9	O4—C16—C17	117.40 (18)
N6—C9—C10	112.0 (3)	C13—C17—C16	122.8 (2)
N6—C9—H9A	109.2	C13—C17—H17	118.6
C10—C9—H9A	109.2	C16—C17—H17	118.6
N6—C9—H9B	109.2	C19—C18—C14	121.1 (2)
C10—C9—H9B	109.2	C19—C18—H18	119.4
H9A—C9—H9B	107.9	C14—C18—H18	119.4
C9—C10—H10A	109.5	C18—C19—C20	119.2 (2)
C9—C10—H10B	109.5	C18—C19—H19	120.4
H10A—C10—H10B	109.5	C20—C19—H19	120.4
C9—C10—H10C	109.5	C21—C20—C19	122.1 (2)
H10A—C10—H10C	109.5	C21—C20—Cl1	118.57 (18)
H10B—C10—H10C	109.5	C19—C20—Cl1	119.29 (17)
N6—C11—S3	124.23 (19)	C15—C21—C20	117.6 (2)
N6—C11—S2	112.71 (17)	C15—C21—H21	121.2
S3—C11—S2	123.04 (15)	C20—C21—H21	121.2
C13—C12—S2	111.11 (15)

C11—N6—C8—C7	−87.5 (3)	C18—C14—C15—C21	−2.1 (3)
C9—N6—C8—C7	92.0 (3)	C13—C14—C15—C21	177.9 (2)
C11—N6—C9—C10	−89.0 (3)	C18—C14—C15—O4	178.11 (19)
C8—N6—C9—C10	91.4 (3)	C13—C14—C15—O4	−2.0 (3)
C9—N6—C11—S3	1.6 (4)	C15—O4—C16—O5	−179.3 (2)
C8—N6—C11—S3	−178.9 (2)	C15—O4—C16—C17	0.9 (3)
C9—N6—C11—S2	−176.8 (2)	C14—C13—C17—C16	0.2 (3)
C8—N6—C11—S2	2.7 (3)	C12—C13—C17—C16	178.6 (2)
C12—S2—C11—N6	−172.85 (18)	O5—C16—C17—C13	178.8 (3)
C12—S2—C11—S3	8.80 (18)	O4—C16—C17—C13	−1.4 (4)
C11—S2—C12—C13	93.46 (17)	C15—C14—C18—C19	1.7 (3)
S2—C12—C13—C17	−108.0 (2)	C13—C14—C18—C19	−178.2 (2)
S2—C12—C13—C14	70.4 (2)	C14—C18—C19—C20	−0.3 (3)
C17—C13—C14—C15	1.4 (3)	C18—C19—C20—C21	−0.8 (4)
C12—C13—C14—C15	−177.0 (2)	C18—C19—C20—Cl1	179.55 (18)
C17—C13—C14—C18	−178.6 (2)	O4—C15—C21—C20	−179.1 (2)
C12—C13—C14—C18	2.9 (3)	C14—C15—C21—C20	1.0 (3)
C16—O4—C15—C21	−179.1 (2)	C19—C20—C21—C15	0.5 (4)
C16—O4—C15—C14	0.8 (3)	Cl1—C20—C21—C15	−179.90 (17)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C14/C15/C18–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O5ⁱ	0.97	2.43	3.264 (3)	144
C18—H18···O5ⁱ	0.93	2.54	3.424 (3)	159
C8—H8A···Cg2ⁱⁱ	0.97	2.95	3.792 (3)	146

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

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C14/C15/C18–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O5ⁱ	0.97	2.43	3.264 (3)	144
C18—H18···O5ⁱ	0.93	2.54	3.424 (3)	159
C8—H8A···Cg2ⁱⁱ	0.97	2.95	3.792 (3)	146

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

Acknowledgements

The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the CCD X-ray facilities, X-ray data collection, GCMS, IR, CHNS and NMR data. One of the authors, KMK is grateful to Karnatak Science College, Dharwad, for providing laboratory facilities.

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Volume 69| Part 9| September 2013| Pages o1431-o1432

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