Crystal structure of 1-ethyl­spiro­[imid­az­olidine-4,1′-indane]-2,5-dione

Hussein, W.M.; Theodore, C.E.; Benaka Prasad, S.B.; Madaiah, M.; Naveen, S.; Lokanath, N.K.

doi:10.1107/S1600536814017097

organic compounds

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Volume 70| Part 9| September 2014| Page o954

doi:10.1107/S1600536814017097

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Crystal structure of 1-ethylspiro[imidazolidine-4,1′-indane]-2,5-dione

Wahraan Mohammed Hussein,^a Cynthia E. Theodore,^b S. B. Benaka Prasad,^b ^* M. Madaiah,^c S. Naveen ^d and N. K. Lokanath ^a

^aDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India, ^bDepartment of Chemistry, School of Engineering and Technology, Jain University, Bangalore 562 112, India, ^cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^dInstitution of Excellence, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: benakaprasad@gmail.com

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 22 July 2014; accepted 24 July 2014; online 1 August 2014)

In the title compound, C₁₃H₁₄N₂O₂, the C₅ ring has an envelope conformation with the C atom adjacent to the quaternary C being the flap. The five atoms comprising the imidazolidine-2,4-dione ring are almost planar (r.m.s. deviation = 0.004 Å). The dihedral angle between the five-membered rings is 89.66 (10)°. In the crystal, inversion-related molecules are connected via {⋯HNCO}₂ synthons. These are linked into a helical supramolecular chain along [010] by C—H⋯O interactions.

Keywords: crystal structure; spiro compounds; hydantoin derivatives; {⋯HNCO}₂ synthons; helical supramolecular chain; C—H⋯O interactions.

CCDC reference: 1015714

1. Related literature

For background to the synthesis and biological activity of hydantoin derivatives, see: Manjunath et al. (2011 , 2012 ). For conformational analysis, see: Cremer & Pople (1975 ).

2. Experimental

2.1. Crystal data

C₁₃H₁₄N₂O₂
M_r = 230.26
Monoclinic, P 2₁ /n
a = 13.7183 (10) Å
b = 6.2040 (5) Å
c = 15.1944 (11) Å
β = 112.865 (3)°
V = 1191.56 (16) Å³
Z = 4
Cu Kα radiation
μ = 0.72 mm⁻¹
T = 296 K
0.23 × 0.22 × 0.21 mm

2.2. Data collection

Bruker X8 Proteum diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ) T_min = 0.867, T_max = 0.867
6730 measured reflections
1953 independent reflections
1742 reflections with I > 2σ(I)
R_int = 0.027

2.3. Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.120
S = 1.07
1953 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H4⋯O7ⁱ	0.86	2.05	2.886 (2)	163
C11—H7⋯O7ⁱⁱ	0.93	2.58	3.501 (2)	173
C17—H10⋯O6ⁱⁱⁱ	0.97	2.56	3.392 (2)	143
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y, -z+2; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2013 ); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

CCDC reference: 1015714

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814017097/tk5331sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814017097/tk5331Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814017097/tk5331Isup3.cml

checkCIF report

Comment top

The chemistry and properties of hydantoins and their derivatives have been investigated for more than 140 years. The hydantoin moiety which is present in various biologically active compounds is of immense pharmaceutical importance. There has been considerable interest in the synthesis and characterization of hydantoin derivatives as an important class of heterocyclic compounds. Hydantoin derivatives that display interesting activities against a broad range of biological targets have been identified. Activity of hydantoin derivatives depends on the nature of substitution of hydantoin rings. As a part of our ongoing research on hydantoins (Manjunath et al., 2012), the synthesis, characterization and the structural work was undertaken on the title compound and herein we report its crystal structure.

The hydantoin ring in the structure is planar within experimental limits with a maximum deviation of 0.0036 (19) Å for C2 atom from the least squares plane of the hydantoin ring. The N—C bong lengths of N1—C2 = 1.394 (2) Å, N1—C5 = 1.367 (2) Å and N3—C2 = 1.337 (2) Å are comparable with the values reported earlier (Manjunath et al., 2011; Manjunath et al., 2012). The shortened bond length values can be attributed to the π-conjugation in the hydantoin ring.

The study of torsion angles, asymmetric parameters and least squares plane reveals that the five membered ring of the bicyclo octane moiety adopts envelope conformation with C4 atom deviating by 0.1121 (17) Å from the least-squares plane (Cremer & Pople, 1975). This is confirmed by the puckering amplitude Q = 0.2163 (19) Å. The hydantoin ring is in a equatorial position with the five membered ring which is evident by the dihedral angle value of 89.66 (10)°. The structure of the molecule is stabilized by the intermolecular hydrogen bonds of the type N—H···O and C—H···O (Table 1).

Related literature top

For background to the synthesis and biological activity of hydantoin derivatives, see: Manjunath et al. (2011, 2012). For conformational analysis, see: Cremer & Pople (1975).

Experimental top

To a solution of 2, 3-dihydrospiro-[imidazoline-4–1-indene]-2,5-dione (1.0 eq) in N,N-dimethylformamide was added anhydrous K₂CO₃ (3.0 eq) followed by stirring for 10 min. 1-Bromoethane (1–1.1eq) was then added. The reaction mixture was stirred at room temperature for 8 h and the progress of the reaction was monitored by TLC. Upon completion, the solvent was removed under reduced pressure and the residue was taken in water and extracted with ethyl acetate. Finally, the organic layer was washed with water and then dried over anhydrous sodium sulfate. The solvent was evaporated. The crude product was purified by column chromatography using chloroform:methanol (9:1) as an eluent. Single crystals were obtained from slow evaporation of its ethylacetate solution.

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view along the b axis of the crystal packing of the title compound.

1-Ethylspiro[imidazolidine-4,1'-indane]-2,5-dione top

Crystal data top

C₁₃H₁₄N₂O₂	Z = 4
M_r = 230.26	F(000) = 488
Monoclinic, P2₁/n	D_x = 1.284 Mg m⁻³
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54178 Å
a = 13.7183 (10) Å	µ = 0.72 mm⁻¹
b = 6.2040 (5) Å	T = 296 K
c = 15.1944 (11) Å	Block, colourless
β = 112.865 (3)°	0.23 × 0.22 × 0.21 mm
V = 1191.56 (16) Å³

Data collection top

Bruker X8 Proteum diffractometer	1742 reflections with I > 2σ(I)
Detector resolution: 10.7 pixels mm^-1	R_int = 0.027
ϕ and ω scans	θ_max = 64.5°, θ_min = 3.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −15→15
T_min = 0.867, T_max = 0.867	k = −3→7
6730 measured reflections	l = −16→17
1953 independent reflections

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0649P)² + 0.277P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
1953 reflections	Δρ_max = 0.23 e Å⁻³
156 parameters	Δρ_min = −0.21 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: 0.0109 (13)

Crystal data top

C₁₃H₁₄N₂O₂	V = 1191.56 (16) Å³
M_r = 230.26	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 13.7183 (10) Å	µ = 0.72 mm⁻¹
b = 6.2040 (5) Å	T = 296 K
c = 15.1944 (11) Å	0.23 × 0.22 × 0.21 mm
β = 112.865 (3)°

Data collection top

Bruker X8 Proteum diffractometer	1953 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	1742 reflections with I > 2σ(I)
T_min = 0.867, T_max = 0.867	R_int = 0.027
6730 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.07	Δρ_max = 0.23 e Å⁻³
1953 reflections	Δρ_min = −0.21 e Å⁻³
156 parameters

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 e.s.d.'s 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 > σ(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
O6	0.76182 (10)	−0.0363 (2)	0.94368 (9)	0.0601 (5)
O7	0.55113 (10)	0.2685 (2)	1.07873 (8)	0.0578 (4)
N1	0.66453 (10)	0.0760 (2)	1.02847 (9)	0.0424 (4)
N3	0.57906 (12)	0.3540 (2)	0.94258 (10)	0.0519 (5)
C2	0.59249 (12)	0.2404 (3)	1.02119 (11)	0.0434 (5)
C4	0.64286 (12)	0.2741 (2)	0.89160 (11)	0.0409 (5)
C5	0.69854 (12)	0.0850 (2)	0.95511 (11)	0.0414 (5)
C8	0.70154 (13)	−0.0797 (3)	1.10674 (12)	0.0510 (5)
C9	0.79910 (18)	−0.0056 (4)	1.18691 (15)	0.0760 (8)
C10	0.57793 (11)	0.2115 (2)	0.78900 (10)	0.0383 (4)
C11	0.50778 (13)	0.0411 (3)	0.75563 (14)	0.0545 (6)
C12	0.45848 (16)	0.0121 (4)	0.65796 (16)	0.0713 (7)
C13	0.47830 (15)	0.1510 (4)	0.59623 (14)	0.0741 (8)
C14	0.54676 (14)	0.3205 (4)	0.62923 (13)	0.0649 (7)
C15	0.59759 (11)	0.3507 (3)	0.72680 (11)	0.0447 (5)
C16	0.67693 (15)	0.5191 (3)	0.77928 (14)	0.0586 (6)
C17	0.72378 (15)	0.4361 (3)	0.88099 (13)	0.0569 (6)
H1	0.85420	0.01810	1.16380	0.1140*
H2	0.44450	0.12930	0.53070	0.0890*
H3	0.78460	0.12630	1.21260	0.1140*
H4	0.53720	0.46290	0.92390	0.0620*
H5	0.55900	0.41400	0.58670	0.0780*
H6	0.41160	−0.10190	0.63380	0.0860*
H7	0.49420	−0.05110	0.79780	0.0650*
H8	0.73090	0.53320	0.75320	0.0700*
H9	0.64310	0.65790	0.77600	0.0700*
H10	0.73560	0.55430	0.92580	0.0680*
H11	0.79080	0.36510	0.89350	0.0680*
H12	0.64620	−0.10350	1.13040	0.0610*
H13	0.71580	−0.21600	1.08280	0.0610*
H14	0.82130	−0.11370	1.23600	0.1140*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O6	0.0622 (8)	0.0624 (8)	0.0613 (8)	0.0248 (6)	0.0301 (6)	0.0006 (6)
O7	0.0702 (8)	0.0651 (8)	0.0502 (7)	0.0260 (6)	0.0366 (6)	0.0125 (6)
N1	0.0483 (7)	0.0410 (7)	0.0397 (7)	0.0137 (5)	0.0190 (6)	0.0071 (5)
N3	0.0724 (9)	0.0482 (8)	0.0425 (8)	0.0301 (7)	0.0305 (7)	0.0115 (6)
C2	0.0505 (9)	0.0436 (8)	0.0382 (8)	0.0131 (7)	0.0195 (7)	0.0021 (7)
C4	0.0489 (8)	0.0398 (8)	0.0373 (8)	0.0060 (6)	0.0205 (7)	−0.0005 (6)
C5	0.0428 (8)	0.0411 (8)	0.0400 (8)	0.0059 (7)	0.0159 (6)	−0.0035 (6)
C8	0.0549 (9)	0.0473 (9)	0.0523 (10)	0.0120 (7)	0.0225 (8)	0.0144 (8)
C9	0.0771 (13)	0.0799 (15)	0.0547 (12)	0.0073 (11)	0.0079 (10)	0.0142 (10)
C10	0.0360 (7)	0.0432 (8)	0.0382 (8)	0.0043 (6)	0.0171 (6)	0.0003 (6)
C11	0.0482 (9)	0.0568 (10)	0.0589 (11)	−0.0082 (8)	0.0211 (8)	−0.0026 (8)
C12	0.0516 (10)	0.0831 (14)	0.0681 (14)	−0.0145 (10)	0.0112 (10)	−0.0207 (11)
C13	0.0497 (10)	0.1212 (19)	0.0424 (10)	−0.0016 (12)	0.0080 (8)	−0.0116 (11)
C14	0.0503 (10)	0.1028 (16)	0.0408 (10)	0.0043 (10)	0.0167 (8)	0.0148 (10)
C15	0.0367 (8)	0.0571 (10)	0.0420 (9)	0.0049 (7)	0.0171 (7)	0.0084 (7)
C16	0.0587 (10)	0.0530 (10)	0.0633 (12)	−0.0060 (8)	0.0230 (9)	0.0116 (9)
C17	0.0621 (10)	0.0521 (10)	0.0516 (10)	−0.0131 (8)	0.0167 (8)	−0.0065 (8)

Geometric parameters (Å, º) top

O6—C5	1.211 (2)	C14—C15	1.384 (2)
O7—C2	1.226 (2)	C15—C16	1.496 (3)
N1—C2	1.394 (2)	C16—C17	1.515 (3)
N1—C5	1.367 (2)	C8—H12	0.9700
N1—C8	1.462 (2)	C8—H13	0.9700
N3—C2	1.337 (2)	C9—H1	0.9600
N3—C4	1.462 (2)	C9—H3	0.9600
N3—H4	0.8600	C9—H14	0.9600
C4—C5	1.523 (2)	C11—H7	0.9300
C4—C10	1.515 (2)	C12—H6	0.9300
C4—C17	1.552 (3)	C13—H2	0.9300
C8—C9	1.490 (3)	C14—H5	0.9300
C10—C11	1.386 (2)	C16—H8	0.9700
C10—C15	1.382 (2)	C16—H9	0.9700
C11—C12	1.383 (3)	C17—H10	0.9700
C12—C13	1.376 (3)	C17—H11	0.9700
C13—C14	1.369 (3)

O6···C17ⁱ	3.392 (2)	C17···H2^x	3.0300
O6···C14ⁱⁱ	3.343 (3)	H1···C5	3.0900
O7···N3ⁱⁱⁱ	2.886 (2)	H1···C13^x	3.0900
O6···H11	2.6800	H1···C14^x	3.0600
O6···H13	2.6700	H2···C13^viii	3.0700
O6···H5ⁱⁱ	2.6900	H2···C17^ix	3.0300
O6···H10ⁱ	2.5600	H2···H11^ix	2.3200
O7···H12	2.6200	H3···H14^iv	2.4900
O7···H14^iv	2.7700	H4···O7ⁱⁱⁱ	2.0500
O7···H4ⁱⁱⁱ	2.0500	H4···C2ⁱⁱⁱ	2.9000
O7···H7^v	2.5800	H5···O6^vi	2.6900
N3···O7ⁱⁱⁱ	2.886 (2)	H7···C5	3.0100
C14···O6^vi	3.343 (3)	H7···O7^v	2.5800
C17···O6^vii	3.392 (2)	H8···C15^vi	2.9900
C2···H4ⁱⁱⁱ	2.9000	H9···C11^vii	2.9600
C5···H1	3.0900	H10···O6^vii	2.5600
C5···H7	3.0100	H11···O6	2.6800
C11···H9ⁱ	2.9600	H11···H2^x	2.3200
C13···H2^viii	3.0700	H12···O7	2.6200
C13···H1^ix	3.0900	H13···O6	2.6700
C14···H1^ix	3.0600	H14···O7^xi	2.7700
C15···H8ⁱⁱ	2.9900	H14···H3^xi	2.4900

C2—N1—C5	111.19 (12)	C4—C17—C16	106.81 (15)
C2—N1—C8	124.02 (14)	N1—C8—H12	109.00
C5—N1—C8	124.75 (14)	N1—C8—H13	109.00
C2—N3—C4	113.05 (14)	C9—C8—H12	109.00
C2—N3—H4	123.00	C9—C8—H13	109.00
C4—N3—H4	123.00	H12—C8—H13	108.00
N1—C2—N3	107.70 (14)	C8—C9—H1	109.00
O7—C2—N1	123.90 (15)	C8—C9—H3	109.00
O7—C2—N3	128.41 (17)	C8—C9—H14	109.00
N3—C4—C17	115.79 (12)	H1—C9—H3	110.00
C5—C4—C10	113.84 (11)	H1—C9—H14	109.00
C5—C4—C17	111.22 (14)	H3—C9—H14	109.00
C10—C4—C17	102.56 (13)	C10—C11—H7	121.00
N3—C4—C5	100.46 (12)	C12—C11—H7	121.00
N3—C4—C10	113.47 (14)	C11—C12—H6	120.00
O6—C5—N1	125.62 (14)	C13—C12—H6	120.00
N1—C5—C4	107.59 (13)	C12—C13—H2	119.00
O6—C5—C4	126.79 (15)	C14—C13—H2	119.00
N1—C8—C9	112.28 (16)	C13—C14—H5	121.00
C4—C10—C15	110.52 (13)	C15—C14—H5	120.00
C4—C10—C11	128.23 (14)	C15—C16—H8	111.00
C11—C10—C15	121.24 (15)	C15—C16—H9	111.00
C10—C11—C12	118.18 (18)	C17—C16—H8	111.00
C11—C12—C13	120.4 (2)	C17—C16—H9	111.00
C12—C13—C14	121.37 (19)	H8—C16—H9	109.00
C13—C14—C15	119.00 (19)	C4—C17—H10	110.00
C10—C15—C16	111.52 (14)	C4—C17—H11	110.00
C10—C15—C14	119.80 (17)	C16—C17—H10	110.00
C14—C15—C16	128.68 (17)	C16—C17—H11	110.00
C15—C16—C17	103.82 (15)	H10—C17—H11	109.00

C5—N1—C2—O7	−179.31 (16)	N3—C4—C10—C15	112.36 (15)
C5—N1—C2—N3	0.70 (19)	C5—C4—C10—C11	45.9 (2)
C8—N1—C2—O7	−1.6 (3)	C5—C4—C10—C15	−133.54 (15)
C8—N1—C2—N3	178.45 (15)	C17—C4—C10—C11	166.16 (17)
C2—N1—C5—O6	179.35 (16)	C17—C4—C10—C15	−13.28 (17)
C2—N1—C5—C4	−0.48 (17)	N3—C4—C17—C16	−103.10 (17)
C8—N1—C5—O6	1.6 (3)	C5—C4—C17—C16	143.07 (15)
C8—N1—C5—C4	−178.21 (14)	C10—C4—C17—C16	21.02 (17)
C2—N1—C8—C9	−90.8 (2)	C4—C10—C11—C12	−178.69 (18)
C5—N1—C8—C9	86.6 (2)	C15—C10—C11—C12	0.7 (3)
C4—N3—C2—O7	179.36 (17)	C4—C10—C15—C14	179.40 (16)
C4—N3—C2—N1	−0.64 (19)	C4—C10—C15—C16	0.3 (2)
C2—N3—C4—C5	0.34 (17)	C11—C10—C15—C14	−0.1 (3)
C2—N3—C4—C10	122.24 (15)	C11—C10—C15—C16	−179.18 (16)
C2—N3—C4—C17	−119.53 (16)	C10—C11—C12—C13	−0.7 (3)
N3—C4—C5—O6	−179.74 (16)	C11—C12—C13—C14	0.0 (4)
N3—C4—C5—N1	0.09 (16)	C12—C13—C14—C15	0.6 (3)
C10—C4—C5—O6	58.6 (2)	C13—C14—C15—C10	−0.6 (3)
C10—C4—C5—N1	−121.54 (15)	C13—C14—C15—C16	178.3 (2)
C17—C4—C5—O6	−56.6 (2)	C10—C15—C16—C17	13.2 (2)
C17—C4—C5—N1	123.20 (14)	C14—C15—C16—C17	−165.8 (2)
N3—C4—C10—C11	−68.2 (2)	C15—C16—C17—C4	−21.00 (19)

Symmetry codes: (i) x, y−1, z; (ii) −x+3/2, y−1/2, −z+3/2; (iii) −x+1, −y+1, −z+2; (iv) −x+3/2, y+1/2, −z+5/2; (v) −x+1, −y, −z+2; (vi) −x+3/2, y+1/2, −z+3/2; (vii) x, y+1, z; (viii) −x+1, −y, −z+1; (ix) x−1/2, −y+1/2, z−1/2; (x) x+1/2, −y+1/2, z+1/2; (xi) −x+3/2, y−1/2, −z+5/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H4···O7ⁱⁱⁱ	0.86	2.05	2.886 (2)	163
C11—H7···O7^v	0.93	2.58	3.501 (2)	173
C17—H10···O6^vii	0.97	2.56	3.392 (2)	143

Symmetry codes: (iii) −x+1, −y+1, −z+2; (v) −x+1, −y, −z+2; (vii) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H4···O7ⁱ	0.86	2.05	2.886 (2)	163
C11—H7···O7ⁱⁱ	0.93	2.58	3.501 (2)	173
C17—H10···O6ⁱⁱⁱ	0.97	2.56	3.392 (2)	143

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

Acknowledgements

The authors are thankful to the IOE, Vijnana Bhavana, University of Mysore, Mysore, for providing the single-crystal X-ray diffraction facility.

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