Methyl N-{4-[(4-meth­oxy­phen­oxy)meth­yl]-2-oxo-2H-chromen-7-yl}carbamate

Kumar, K.M.; Mahabaleshwaraiah, N.M.; Kotresh, O.; Jeyaseelan, S.; Devarajegowda, H.C.

doi:10.1107/S160053681202048X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1734

doi:10.1107/S160053681202048X

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Methyl N-{4-[(4-methoxyphenoxy)methyl]-2-oxo-2H-chromen-7-yl}carbamate

K. Mahesh Kumar,^a N. M. Mahabaleshwaraiah,^a O. Kotresh,^a S Jeyaseelan ^b and H. C. Devarajegowda ^b ^*

^aDepartment of Chemistry, Karnatak Science College, Dharwad 580 001, Karnataka, India, and ^bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 23 April 2012; accepted 7 May 2012; online 16 May 2012)

In the title compound, C₁₉H₁₇NO₆, the dihedral angle between the 2H-chromene ring system and benzene ring is 5.34 (6)°. A short intramolecular C—H⋯O contact occurs. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, generating C(8) chains propagating in [010]. The chains are linked by C—H⋯O interactions and the packing also exhibits π–π stacking interactions between benzene and pyran rings, with a centroid–centroid distance of 3.676 (9) Å.

Related literature

For a related structure and background to coumarins, see: Mahabaleshwaraiah et al. (2012 ). For further synthetic details, see: Kulkarni & Patil (1981 ).

Experimental

Crystal data

C₁₉H₁₇NO₆
M_r = 355.34
Monoclinic, P 2₁ /n
a = 8.3141 (1) Å
b = 17.3978 (3) Å
c = 11.5729 (2) Å
β = 94.309 (1)°
V = 1669.25 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.770, T_max = 1.000
14973 measured reflections
2939 independent reflections
2374 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.103
S = 1.06
2939 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O2ⁱ	0.86	1.99	2.8428 (16)	170
C15—H15⋯O5	0.93	2.30	2.8764 (19)	120
C19—H19A⋯O5ⁱⁱ	0.97	2.53	3.476 (2)	165
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y, z.

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 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681202048X/hb6754sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681202048X/hb6754Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681202048X/hb6754Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of coumarin derivatives with possible biological activity (Mahabaleshwaraiah et al., 2012), we now describe the structure of the title compound (Fig. 1).

The 2H-chromene (O1/C10–C18) and benzene (C20–C25) rings are almost coplanar; the dihedral angle between them is 5.34 (6)°. In the crystal, (Fig. 2), the molecules are connected by C19—H19A···O5 and N7—H7···O2 interaction hydrogen bonds.(Table 1) Furthermore, the crystal structure features π-π stacking interactions between pyranCg2 and benzeneCg3 rings, with a centroid Cg2 (O3/C12–C16) -centroid Cg3 (C13/C14/C17–C20) distance of 3.676 (9) Å.

Related literature top

For a related structure and background to coumarins, see: Mahabaleshwaraiah et al. (2012). For further synthetic details, see: Kulkarni & Patil (1981).

Experimental top

The 4-bromomethyl coumarin required for the target molecule was synthesized according to an already reported (Kulkarni et al.1981) procedure involving Pechmann cyclization of phenols with 4-bromoethylacetoacetate. A mixture of 1.56 g (0.005 mol) of 7-carbonylamino-4-bromomethyl coumarin, 0.620 g (0.005 mol) of p-methoxy phenol and 0.70 g (0.005 mol) of powdered anhydrous K₂CO₃ in 30 ml of dry acetone were stirred at room temperature for 24 h. After completion of the reaction, the s eparated solid was filtered, washed with excess of dilute (10%) hydrochloric acid (50 ml) and then with an excess of cold water, dried and crystallized twice from ethanol & 1,4-dioxane mixture to yield colourless plates. Yield= 78%, M. P.475 K.

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 (Farrugia, 1997); 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. Dashed lines indicate intramolecular hydrogen bonds.
	Fig. 2. The packing of the molecules in the title structure.

Methyl N-{4-[(4-methoxyphenoxy)methyl]-2-oxo-2H-chromen-7-yl}carbamate top

Crystal data top

C₁₉H₁₇NO₆	F(000) = 744
M_r = 355.34	D_x = 1.414 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 475 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.3141 (1) Å	Cell parameters from 2939 reflections
b = 17.3978 (3) Å	θ = 2.1–25.0°
c = 11.5729 (2) Å	µ = 0.11 mm⁻¹
β = 94.309 (1)°	T = 293 K
V = 1669.25 (5) Å³	Plate, colourless
Z = 4	0.24 × 0.20 × 0.12 mm

Data collection top

Bruker SMART CCD diffractometer	2939 independent reflections
Radiation source: fine-focus sealed tube	2374 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω and ϕ scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −9→9
T_min = 0.770, T_max = 1.000	k = −20→20
14973 measured reflections	l = −13→13

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0518P)² + 0.2287P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2939 reflections	Δρ_max = 0.14 e Å⁻³
238 parameters	Δρ_min = −0.12 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: 0.0028 (9)

Crystal data top

C₁₉H₁₇NO₆	V = 1669.25 (5) Å³
M_r = 355.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.3141 (1) Å	µ = 0.11 mm⁻¹
b = 17.3978 (3) Å	T = 293 K
c = 11.5729 (2) Å	0.24 × 0.20 × 0.12 mm
β = 94.309 (1)°

Data collection top

Bruker SMART CCD diffractometer	2939 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2374 reflections with I > 2σ(I)
T_min = 0.770, T_max = 1.000	R_int = 0.023
14973 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.06	Δρ_max = 0.14 e Å⁻³
2939 reflections	Δρ_min = −0.12 e Å⁻³
238 parameters

Special details top

Experimental. IR(KBr): 1067 cm^-1(C—O—C), 1697 cm^-1 (NH—C=O), 1727 cm^-1 (Coumarin C=O), 3261 cm^-1 (NH). GCMS: m/e: 355.1H NMR (500 MHz, DMSO.D6, \?, p.p.m.): 3.34 (s,3H, C₁₃), 3.696(s,3H, C₁), 5.2 (s,2H, C₆), 6.38 (s 1H, C₁₇), 6.88 (d,2H, C₃ & C₁₅), 7.04 (s,2H, C₄ & C₁₄), 7.38 (s,1H, C₁₉), 7.56 (s,1H, C₁₀),7.74 (s,1H, C₁₈). Elemental analysis: C, 64.20; H, 4.78; N, 3.91; O, 27.19.

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
O1	0.22869 (12)	0.25228 (5)	0.17803 (9)	0.0546 (3)
O2	0.29518 (15)	0.36749 (6)	0.12426 (11)	0.0719 (4)
O3	0.75136 (12)	0.21340 (6)	0.00648 (10)	0.0625 (3)
O4	1.32758 (14)	0.12805 (7)	−0.16477 (12)	0.0738 (4)
O5	−0.16647 (14)	0.08777 (7)	0.31601 (12)	0.0798 (4)
O6	−0.15645 (12)	−0.02844 (7)	0.40139 (10)	0.0651 (3)
N7	0.05554 (14)	0.01046 (7)	0.31564 (11)	0.0551 (3)
H7	0.0887	−0.0347	0.3359	0.066*
C8	−0.3183 (2)	−0.01795 (12)	0.43264 (17)	0.0758 (5)
H8A	−0.3253	0.0291	0.4753	0.114*
H8B	−0.3480	−0.0603	0.4798	0.114*
H8C	−0.3901	−0.0157	0.3638	0.114*
C9	−0.09510 (18)	0.02930 (9)	0.34198 (14)	0.0547 (4)
C10	0.16316 (16)	0.05609 (8)	0.25940 (12)	0.0482 (3)
C11	0.30076 (18)	0.02083 (9)	0.22107 (14)	0.0556 (4)
H11	0.3157	−0.0318	0.2316	0.067*
C12	0.41361 (18)	0.06269 (9)	0.16825 (14)	0.0548 (4)
H12	0.5041	0.0380	0.1435	0.066*
C13	0.39578 (16)	0.14200 (8)	0.15063 (12)	0.0465 (3)
C14	0.25774 (17)	0.17482 (8)	0.18963 (12)	0.0468 (3)
C15	0.14222 (17)	0.13397 (8)	0.24295 (13)	0.0503 (4)
H15	0.0515	0.1586	0.2675	0.060*
C16	0.33358 (18)	0.30026 (9)	0.12863 (14)	0.0544 (4)
C17	0.47631 (18)	0.26706 (9)	0.08719 (14)	0.0534 (4)
H17	0.5491	0.2987	0.0527	0.064*
C18	0.50789 (16)	0.19144 (8)	0.09682 (12)	0.0486 (4)
C19	0.65617 (17)	0.15584 (9)	0.05426 (14)	0.0543 (4)
H19A	0.7178	0.1306	0.1179	0.065*
H19B	0.6260	0.1175	−0.0042	0.065*
C20	0.89376 (17)	0.18941 (9)	−0.03564 (13)	0.0515 (4)
C21	0.94292 (19)	0.11408 (9)	−0.04124 (15)	0.0598 (4)
H21	0.8782	0.0751	−0.0152	0.072*
C22	1.08779 (19)	0.09621 (9)	−0.08528 (15)	0.0612 (4)
H22	1.1200	0.0451	−0.0885	0.073*
C23	1.18506 (18)	0.15266 (9)	−0.12443 (13)	0.0547 (4)
C24	1.13658 (18)	0.22857 (9)	−0.11907 (13)	0.0563 (4)
H24	1.2015	0.2674	−0.1453	0.068*
C25	0.99133 (18)	0.24652 (9)	−0.07463 (13)	0.0552 (4)
H25	0.9591	0.2976	−0.0710	0.066*
C26	1.4187 (2)	0.18198 (11)	−0.22267 (18)	0.0783 (5)
H26A	1.3534	0.2034	−0.2866	0.118*
H26B	1.5110	0.1570	−0.2509	0.118*
H26C	1.4538	0.2223	−0.1700	0.118*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0545 (6)	0.0394 (6)	0.0714 (7)	0.0001 (4)	0.0157 (5)	−0.0011 (5)
O2	0.0771 (8)	0.0378 (6)	0.1031 (10)	−0.0030 (5)	0.0219 (7)	−0.0017 (6)
O3	0.0518 (6)	0.0560 (6)	0.0820 (8)	−0.0025 (5)	0.0206 (6)	0.0081 (6)
O4	0.0598 (7)	0.0671 (8)	0.0982 (9)	0.0010 (6)	0.0296 (6)	0.0054 (6)
O5	0.0574 (7)	0.0748 (9)	0.1098 (10)	0.0136 (6)	0.0223 (7)	0.0293 (7)
O6	0.0536 (6)	0.0648 (7)	0.0789 (8)	−0.0073 (5)	0.0184 (5)	0.0110 (6)
N7	0.0505 (7)	0.0444 (7)	0.0720 (9)	0.0020 (5)	0.0150 (6)	0.0087 (6)
C8	0.0518 (10)	0.0929 (14)	0.0848 (13)	−0.0122 (9)	0.0191 (9)	0.0062 (10)
C9	0.0506 (9)	0.0549 (10)	0.0594 (9)	−0.0030 (7)	0.0082 (7)	0.0061 (7)
C10	0.0459 (8)	0.0465 (8)	0.0527 (8)	−0.0009 (6)	0.0060 (6)	0.0028 (6)
C11	0.0523 (8)	0.0436 (8)	0.0720 (10)	0.0045 (6)	0.0119 (7)	0.0063 (7)
C12	0.0474 (8)	0.0506 (9)	0.0677 (10)	0.0064 (6)	0.0129 (7)	0.0040 (7)
C13	0.0432 (7)	0.0459 (8)	0.0504 (8)	−0.0012 (6)	0.0038 (6)	−0.0007 (6)
C14	0.0480 (8)	0.0402 (8)	0.0522 (8)	0.0009 (6)	0.0038 (6)	−0.0015 (6)
C15	0.0456 (8)	0.0475 (9)	0.0591 (9)	0.0016 (6)	0.0122 (7)	−0.0011 (7)
C16	0.0574 (9)	0.0429 (9)	0.0633 (10)	−0.0069 (7)	0.0070 (7)	−0.0035 (7)
C17	0.0507 (8)	0.0481 (9)	0.0619 (9)	−0.0091 (7)	0.0088 (7)	0.0007 (7)
C18	0.0432 (8)	0.0526 (9)	0.0499 (8)	−0.0042 (6)	0.0016 (6)	−0.0008 (6)
C19	0.0473 (8)	0.0540 (9)	0.0627 (9)	−0.0038 (7)	0.0109 (7)	0.0067 (7)
C20	0.0457 (8)	0.0563 (9)	0.0529 (8)	−0.0042 (7)	0.0058 (6)	0.0023 (7)
C21	0.0552 (9)	0.0511 (9)	0.0746 (11)	−0.0092 (7)	0.0153 (8)	0.0063 (8)
C22	0.0600 (10)	0.0493 (9)	0.0753 (11)	−0.0024 (7)	0.0126 (8)	0.0024 (8)
C23	0.0493 (8)	0.0577 (10)	0.0576 (9)	−0.0024 (7)	0.0077 (7)	0.0005 (7)
C24	0.0536 (9)	0.0550 (9)	0.0612 (9)	−0.0106 (7)	0.0093 (7)	0.0059 (7)
C25	0.0557 (9)	0.0488 (9)	0.0615 (9)	−0.0045 (7)	0.0076 (7)	0.0037 (7)
C26	0.0662 (11)	0.0834 (13)	0.0892 (13)	−0.0052 (9)	0.0309 (10)	0.0102 (10)

Geometric parameters (Å, º) top

O1—C16	1.3636 (17)	C13—C18	1.4435 (19)
O1—C14	1.3738 (16)	C14—C15	1.3774 (19)
O2—C16	1.2124 (18)	C15—H15	0.9300
O3—C20	1.3786 (18)	C16—C17	1.434 (2)
O3—C19	1.4144 (17)	C17—C18	1.345 (2)
O4—C23	1.3742 (18)	C17—H17	0.9300
O4—C26	1.407 (2)	C18—C19	1.496 (2)
O5—C9	1.2042 (19)	C19—H19A	0.9700
O6—C9	1.3397 (18)	C19—H19B	0.9700
O6—C8	1.4309 (19)	C20—C21	1.376 (2)
N7—C9	1.3514 (19)	C20—C25	1.380 (2)
N7—C10	1.3935 (18)	C21—C22	1.378 (2)
N7—H7	0.8600	C21—H21	0.9300
C8—H8A	0.9600	C22—C23	1.371 (2)
C8—H8B	0.9600	C22—H22	0.9300
C8—H8C	0.9600	C23—C24	1.384 (2)
C10—C15	1.377 (2)	C24—C25	1.383 (2)
C10—C11	1.3993 (19)	C24—H24	0.9300
C11—C12	1.368 (2)	C25—H25	0.9300
C11—H11	0.9300	C26—H26A	0.9600
C12—C13	1.401 (2)	C26—H26B	0.9600
C12—H12	0.9300	C26—H26C	0.9600
C13—C14	1.3874 (19)

C16—O1—C14	121.89 (11)	C18—C17—C16	121.85 (14)
C20—O3—C19	116.39 (12)	C18—C17—H17	119.1
C23—O4—C26	117.57 (13)	C16—C17—H17	119.1
C9—O6—C8	115.81 (13)	C17—C18—C13	119.37 (13)
C9—N7—C10	127.28 (13)	C17—C18—C19	122.58 (13)
C9—N7—H7	116.4	C13—C18—C19	118.05 (13)
C10—N7—H7	116.4	O3—C19—C18	109.56 (12)
O6—C8—H8A	109.5	O3—C19—H19A	109.8
O6—C8—H8B	109.5	C18—C19—H19A	109.8
H8A—C8—H8B	109.5	O3—C19—H19B	109.8
O6—C8—H8C	109.5	C18—C19—H19B	109.8
H8A—C8—H8C	109.5	H19A—C19—H19B	108.2
H8B—C8—H8C	109.5	C21—C20—O3	124.84 (13)
O5—C9—O6	124.20 (14)	C21—C20—C25	119.12 (14)
O5—C9—N7	126.60 (14)	O3—C20—C25	116.05 (14)
O6—C9—N7	109.20 (13)	C20—C21—C22	120.22 (15)
C15—C10—N7	123.09 (13)	C20—C21—H21	119.9
C15—C10—C11	119.03 (13)	C22—C21—H21	119.9
N7—C10—C11	117.86 (13)	C23—C22—C21	120.96 (15)
C12—C11—C10	120.86 (14)	C23—C22—H22	119.5
C12—C11—H11	119.6	C21—C22—H22	119.5
C10—C11—H11	119.6	C22—C23—O4	115.74 (14)
C11—C12—C13	121.39 (14)	C22—C23—C24	119.20 (14)
C11—C12—H12	119.3	O4—C23—C24	125.05 (14)
C13—C12—H12	119.3	C25—C24—C23	119.85 (14)
C14—C13—C12	116.04 (13)	C25—C24—H24	120.1
C14—C13—C18	118.16 (13)	C23—C24—H24	120.1
C12—C13—C18	125.80 (13)	C20—C25—C24	120.66 (15)
O1—C14—C15	115.25 (12)	C20—C25—H25	119.7
O1—C14—C13	121.04 (12)	C24—C25—H25	119.7
C15—C14—C13	123.71 (13)	O4—C26—H26A	109.5
C10—C15—C14	118.97 (13)	O4—C26—H26B	109.5
C10—C15—H15	120.5	H26A—C26—H26B	109.5
C14—C15—H15	120.5	O4—C26—H26C	109.5
O2—C16—O1	115.68 (14)	H26A—C26—H26C	109.5
O2—C16—C17	126.62 (14)	H26B—C26—H26C	109.5
O1—C16—C17	117.70 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O2ⁱ	0.86	1.99	2.8428 (16)	170
C15—H15···O5	0.93	2.30	2.8764 (19)	120
C19—H19A···O5ⁱⁱ	0.97	2.53	3.476 (2)	165

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇NO₆
M_r	355.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.3141 (1), 17.3978 (3), 11.5729 (2)
β (°)	94.309 (1)
V (Å³)	1669.25 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.24 × 0.20 × 0.12

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.770, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14973, 2939, 2374
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.103, 1.06
No. of reflections	2939
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.12

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O2ⁱ	0.86	1.99	2.8428 (16)	170
C15—H15···O5	0.93	2.30	2.8764 (19)	120
C19—H19A···O5ⁱⁱ	0.97	2.53	3.476 (2)	165

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

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. KMK is grateful to Karnatak Science College, Dharwad, for providing laboratory facilities.

References

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Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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