Crystal structure of 1′-(2-methyl­prop­yl)-2,3-di­hydro­spiro­[1-benzo­thio­pyran-4,4′-imidazolidine]-2′,5′-dione

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

doi:10.1107/S1600536814018030

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1043-o1044

doi:10.1107/S1600536814018030

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Crystal structure of 1′-(2-methylpropyl)-2,3-dihydrospiro[1-benzothiopyran-4,4′-imidazolidine]-2′,5′-dione

Cynthia E. Theodore,^a S. Naveen,^b S. B. Benaka Prasad,^a M. Madaiah,^c C. S. Ananda Kumar ^d and N. K. Lokanath ^e ^*

^aDepartment of Chemistry, School of Engineering and Technology, Jain University, Bangalore 562 112, India, ^bInstitution of Excellence, University of Mysore, Manasagangotri, Mysore 570 006, India, ^cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, ^dDepartment of Nanotechnology, Center for Post Graduate Studies, Visveswaraya Technological University, Bangalore 560 018, India, and ^eDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore m570 006, India
^*Correspondence e-mail: benakaprasad@gmail.com

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 31 July 2014; accepted 6 August 2014; online 23 August 2014)

In the title compound, C₁₅H₁₈N₂O₂S, the 2,3-dihydro-1-benzothiopyran ring adopts a sofa conformation and the hydantoin ring is twisted with respect to the benzene ring at 78.73 (17)°. In the crystal, pairs of N—H⋯O hydrogen bonds link the molecules into inversion dimers.

Keywords: crystal structure; hydantoin compounds; hydrogen bonding; spiro[1-benzothiopyran-4,4′-imidazolidine].

CCDC reference: 1018087

1. Related literature

For background and applications of hydantoin compounds, see: Nefzi et al. (2002 ); Park & Kurth (2000 ); Manjunath et al. (2012 ); Hussein et al. (2014 ). For related structures, see: Manjunath et al. (2011 ); Hussein et al. (2014).

2. Experimental

2.1. Crystal data

C₁₅H₁₈N₂O₂S
M_r = 290.38
Monoclinic, P 2₁ /c
a = 13.279 (3) Å
b = 9.939 (3) Å
c = 13.264 (3) Å
β = 118.56 (1)°
V = 1537.6 (7) Å³
Z = 4
Cu Kα radiation
μ = 1.90 mm⁻¹
T = 296 K
0.20 × 0.15 × 0.15 mm

2.2. Data collection

Bruker X8 Proteum diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.747, T_max = 0.753
5024 measured reflections
2397 independent reflections
1959 reflections with I > 2σ(I)
R_int = 0.067

2.3. Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.195
S = 1.06
2397 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11⋯O16ⁱ	0.86	2.03	2.850 (3)	160
Symmetry code: (i) -x+1, -y+1, -z+1.

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: 1018087

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814018030/xu5809sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814018030/xu5809Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814018030/xu5809Isup3.cml

checkCIF report

Comment top

The combinatorial generation of organic compound libraries has emerged as a powerful tool for drug discovery. Small substituted heterocyclic compounds play an important role in the development of biologically active substances by offering a high structural diversity. Among such heterocycles, particularly the hydantoin scaffold opens the possibility of different kinds and degrees of substitution. They have been the focus of attention as a ubiquitous moiety incorporated into compounds with numerous biological activities and therapeutic applications (Nefzi et al., 2002). A variety of combinatorial approaches have been described by which pharmacophoric groups were attached to such a relatively rigid scaffold (Park & Kurth, 2000). Therefore, the chemistry of multiple substituted hydantoins has newly attracted much interest, and traditional approaches have been combined with recently developed strategies. Hence as a part of our ongoing research on hydantoins (Manjunath et al., 2012; Hussein et al., 2014), the synthesis, characterization and the structural work of the title compound was undertaken and herein we report its crystal structure.

The hydantoin ring in the structure is planar within the experimental limits with a maximum deviation of 0.012 (2) Å for N1 atom from the least-squares plane of the hydantoin ring. The N—C bong length values of N11—C12 = 1.349 (3) Å, N13—C12 = 1.400 (4) Å and N13—C14 = 1.359 (2) Å are comparable with the values reported earlier (Manjunath et al., 2011; Hussein et al., 2014). The shortened bond length values can be attributed to the π conjugation in the hydantoin ring. The isobutyl group is twisted out of the plane of the hydantoin ring as indicated by the torsion angle values of -175.6 (3)° and 61.5 (3)° for the atoms N13—C17—C18—C20 and N13—C17—C18—C19 indicating that they are in antiperiplanar and synclinal conformations respectively.

The study of torsion angles, asymmetric parameters and least-squares plane reveals that the 2,3-dihydro-1-benzothiopyran ring in the structure adopts envelope conformation with S1 atom deviating by 0.0851 (14) Å from the least-squares plane. This is confirmed by the puckering amplitude Q = 0.519 (3) Å. The hydantoin ring is in a equatorial position with the 2,3-dihydro-1-benzothiopyran ring which is evident by the dihedral angle of 81.15 (15)°. This value is slightly lesser than the value reported earlier (Hussein et al., 2014) for 1-ethyl-2',3'-dihydrospiro[imidazoline-4,1-indene]-2,5-dione. The molecules are interlinked by N—H···O hydrogen bonds to form inverted dimers.

Related literature top

For background and applications of hydantoin compounds, see: Nefzi et al. (2002); Park & Kurth (2000); Manjunath et al. (2012); Hussein et al. (2014). For related structures, see: Manjunath et al. (2011); Hussein et al. (2014).

Experimental top

A solution of spiro[1-benzothiopyran-4,4'-imidazolidine]-2',5'-dione (1.0 eq) in N,N-dimethylformamide was taken, anhydrous K₂CO₃ (3.0 eq) was added to the solution and stirred for 10 min. 1-Bromo–2 methyl propane (1–1.1 eq) 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 water wash was given to the organic layer and 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 solvent.

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 of the crystal packing of the title compound showing inverted dimers.

1'-(2-Methylpropyl)-2,3-dihydrospiro[1-benzothiopyran-4,4'-imidazolidine]-2',5'-dione top

Crystal data top

C₁₅H₁₈N₂O₂S	Z = 4
M_r = 290.38	F(000) = 616
Monoclinic, P2₁/c	D_x = 1.254 Mg m⁻³
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 13.279 (3) Å	µ = 1.90 mm⁻¹
b = 9.939 (3) Å	T = 296 K
c = 13.264 (3) Å	Block, yellow
β = 118.56 (1)°	0.20 × 0.15 × 0.15 mm
V = 1537.6 (7) Å³

Data collection top

Bruker X8 Proteum diffractometer	1959 reflections with I > 2σ(I)
Detector resolution: 18.4 pixels mm^-1	R_int = 0.067
ϕ and ω scans	θ_max = 64.2°, θ_min = 3.8°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −15→14
T_min = 0.747, T_max = 0.753	k = −8→11
5024 measured reflections	l = −11→15
2397 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)] = 0.066	H-atom parameters constrained
wR(F²) = 0.195	w = 1/[σ²(F_o²) + (0.1345P)² + 0.3286P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2397 reflections	Δρ_max = 0.43 e Å⁻³
184 parameters	Δρ_min = −0.47 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: 0.0092 (15)

Crystal data top

C₁₅H₁₈N₂O₂S	V = 1537.6 (7) Å³
M_r = 290.38	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 13.279 (3) Å	µ = 1.90 mm⁻¹
b = 9.939 (3) Å	T = 296 K
c = 13.264 (3) Å	0.20 × 0.15 × 0.15 mm
β = 118.56 (1)°

Data collection top

Bruker X8 Proteum diffractometer	2397 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	1959 reflections with I > 2σ(I)
T_min = 0.747, T_max = 0.753	R_int = 0.067
5024 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.195	H-atom parameters constrained
S = 1.06	Δρ_max = 0.43 e Å⁻³
2397 reflections	Δρ_min = −0.47 e Å⁻³
184 parameters

Special details top

Experimental. H¹NMR (DMSO, 400 MHz) δ:9.0(s, 1H, –NH), δ:7.2(m, 2H, Ar—H) δ:7.1(m, 2H, Ar—H) δ:3.3(d, 2H, –CH₂–)δ:3.1(m, 2H, –CH₂–) δ:2.1(m, 1H, –CH–) δ:0.9(m, 6H, –CH₃–). Melting point 636.52 K.

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
S1	0.50647 (7)	0.34459 (8)	0.13658 (6)	0.0529 (3)
O15	0.8299 (2)	0.2088 (3)	0.52413 (19)	0.0547 (8)
O16	0.62741 (16)	0.4706 (2)	0.64774 (16)	0.0400 (6)
N11	0.59964 (19)	0.4235 (2)	0.46550 (18)	0.0348 (7)
N13	0.75117 (18)	0.3354 (2)	0.61452 (18)	0.0305 (7)
C2	0.4715 (3)	0.2679 (3)	0.2388 (3)	0.0490 (10)
C3	0.5783 (3)	0.2225 (3)	0.3462 (2)	0.0426 (9)
C4	0.6545 (2)	0.3412 (2)	0.4141 (2)	0.0302 (8)
C5	0.6935 (2)	0.4273 (3)	0.3446 (2)	0.0343 (8)
C6	0.7916 (3)	0.5061 (3)	0.4013 (3)	0.0487 (10)
C7	0.8306 (3)	0.5889 (4)	0.3438 (3)	0.0629 (12)
C8	0.7704 (4)	0.5939 (4)	0.2254 (3)	0.0637 (12)
C9	0.6728 (3)	0.5174 (4)	0.1671 (3)	0.0521 (11)
C10	0.6325 (3)	0.4346 (3)	0.2243 (2)	0.0374 (8)
C12	0.6543 (2)	0.4167 (3)	0.5811 (2)	0.0299 (7)
C14	0.7571 (2)	0.2853 (3)	0.5222 (2)	0.0342 (8)
C17	0.8345 (2)	0.3059 (3)	0.7353 (2)	0.0362 (8)
C18	0.9406 (3)	0.3929 (4)	0.7806 (2)	0.0475 (10)
C19	0.9119 (4)	0.5421 (4)	0.7785 (4)	0.0785 (16)
C20	1.0243 (3)	0.3466 (5)	0.9022 (3)	0.0727 (16)
H2A	0.42970	0.33190	0.26000	0.0590*
H2B	0.42210	0.19100	0.20360	0.0590*
H3A	0.62210	0.16230	0.32440	0.0510*
H3B	0.55560	0.17280	0.39500	0.0510*
H6	0.83250	0.50270	0.48100	0.0580*
H7	0.89640	0.64050	0.38410	0.0760*
H8	0.79560	0.64880	0.18520	0.0770*
H9	0.63290	0.52130	0.08730	0.0630*
H11	0.53910	0.47100	0.42630	0.0420*
H17A	0.85700	0.21210	0.74160	0.0430*
H17B	0.79780	0.31930	0.78250	0.0430*
H18	0.97670	0.37940	0.73190	0.0570*
H19A	0.86290	0.56990	0.70070	0.1180*
H19B	0.98140	0.59390	0.81030	0.1180*
H19C	0.87330	0.55640	0.82310	0.1180*
H20A	0.99140	0.36250	0.95170	0.1090*
H20B	1.09470	0.39600	0.92990	0.1090*
H20C	1.03950	0.25230	0.90150	0.1090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0564 (6)	0.0552 (6)	0.0243 (5)	0.0026 (4)	0.0009 (4)	0.0035 (3)
O15	0.0531 (13)	0.0668 (15)	0.0394 (12)	0.0333 (12)	0.0183 (10)	0.0072 (11)
O16	0.0359 (10)	0.0554 (12)	0.0244 (10)	0.0082 (9)	0.0109 (8)	−0.0034 (8)
N11	0.0302 (11)	0.0462 (13)	0.0214 (11)	0.0122 (10)	0.0071 (9)	0.0028 (9)
N13	0.0249 (11)	0.0396 (12)	0.0168 (11)	0.0062 (9)	0.0017 (9)	0.0031 (9)
C2	0.0441 (17)	0.0490 (17)	0.0367 (16)	−0.0070 (13)	0.0055 (14)	−0.0110 (13)
C3	0.0496 (17)	0.0408 (16)	0.0319 (15)	−0.0034 (13)	0.0151 (13)	0.0008 (12)
C4	0.0347 (14)	0.0328 (14)	0.0190 (13)	0.0056 (10)	0.0096 (11)	−0.0007 (10)
C5	0.0384 (14)	0.0352 (14)	0.0269 (14)	0.0059 (11)	0.0136 (11)	0.0001 (11)
C6	0.0464 (17)	0.0569 (19)	0.0367 (17)	−0.0064 (14)	0.0149 (14)	−0.0048 (14)
C7	0.060 (2)	0.072 (2)	0.059 (2)	−0.0149 (18)	0.0302 (18)	0.0002 (19)
C8	0.070 (2)	0.068 (2)	0.065 (2)	0.0000 (19)	0.042 (2)	0.0157 (19)
C9	0.064 (2)	0.0580 (19)	0.0363 (16)	0.0142 (16)	0.0257 (15)	0.0160 (15)
C10	0.0446 (15)	0.0382 (14)	0.0251 (13)	0.0128 (12)	0.0133 (12)	0.0049 (11)
C12	0.0256 (12)	0.0374 (13)	0.0217 (13)	0.0014 (10)	0.0073 (10)	0.0003 (10)
C14	0.0326 (13)	0.0360 (14)	0.0288 (14)	0.0089 (11)	0.0105 (11)	0.0032 (11)
C17	0.0296 (13)	0.0460 (15)	0.0220 (13)	0.0051 (11)	0.0034 (11)	0.0096 (11)
C18	0.0305 (14)	0.078 (2)	0.0244 (15)	−0.0055 (14)	0.0053 (12)	0.0011 (14)
C19	0.074 (3)	0.063 (2)	0.062 (3)	−0.026 (2)	0.003 (2)	−0.0043 (19)
C20	0.0395 (18)	0.125 (4)	0.0326 (18)	0.005 (2)	0.0003 (15)	0.007 (2)

Geometric parameters (Å, º) top

S1—C2	1.799 (4)	C17—C18	1.511 (5)
S1—C10	1.759 (3)	C18—C19	1.528 (6)
O15—C14	1.221 (4)	C18—C20	1.528 (5)
O16—C12	1.224 (3)	C2—H2A	0.9700
N11—C4	1.463 (4)	C2—H2B	0.9700
N11—C12	1.349 (3)	C3—H3A	0.9700
N13—C12	1.400 (4)	C3—H3B	0.9700
N13—C14	1.359 (3)	C6—H6	0.9300
N13—C17	1.477 (3)	C7—H7	0.9300
N11—H11	0.8600	C8—H8	0.9300
C2—C3	1.521 (5)	C9—H9	0.9300
C3—C4	1.535 (4)	C17—H17A	0.9700
C4—C5	1.519 (4)	C17—H17B	0.9700
C4—C14	1.534 (4)	C18—H18	0.9800
C5—C6	1.393 (5)	C19—H19A	0.9600
C5—C10	1.404 (3)	C19—H19B	0.9600
C6—C7	1.380 (6)	C19—H19C	0.9600
C7—C8	1.381 (5)	C20—H20A	0.9600
C8—C9	1.378 (6)	C20—H20B	0.9600
C9—C10	1.388 (5)	C20—H20C	0.9600

C2—S1—C10	102.93 (16)	C3—C2—H2A	109.00
C4—N11—C12	112.6 (2)	C3—C2—H2B	109.00
C12—N13—C14	111.5 (2)	H2A—C2—H2B	108.00
C12—N13—C17	123.8 (2)	C2—C3—H3A	109.00
C14—N13—C17	124.7 (2)	C2—C3—H3B	109.00
C12—N11—H11	124.00	C4—C3—H3A	109.00
C4—N11—H11	124.00	C4—C3—H3B	109.00
S1—C2—C3	111.8 (3)	H3A—C3—H3B	108.00
C2—C3—C4	112.3 (2)	C5—C6—H6	119.00
N11—C4—C3	111.6 (3)	C7—C6—H6	119.00
C3—C4—C5	113.4 (2)	C6—C7—H7	121.00
N11—C4—C5	110.99 (19)	C8—C7—H7	120.00
N11—C4—C14	100.64 (19)	C7—C8—H8	120.00
C5—C4—C14	111.3 (2)	C9—C8—H8	120.00
C3—C4—C14	108.2 (2)	C8—C9—H9	119.00
C4—C5—C10	122.7 (3)	C10—C9—H9	119.00
C4—C5—C6	119.4 (2)	N13—C17—H17A	109.00
C6—C5—C10	117.9 (3)	N13—C17—H17B	109.00
C5—C6—C7	122.6 (3)	C18—C17—H17A	109.00
C6—C7—C8	118.9 (4)	C18—C17—H17B	109.00
C7—C8—C9	119.8 (4)	H17A—C17—H17B	108.00
C8—C9—C10	121.7 (3)	C17—C18—H18	108.00
S1—C10—C9	115.7 (2)	C19—C18—H18	108.00
C5—C10—C9	119.2 (3)	C20—C18—H18	108.00
S1—C10—C5	125.1 (3)	C18—C19—H19A	109.00
N11—C12—N13	107.6 (2)	C18—C19—H19B	109.00
O16—C12—N11	128.0 (3)	C18—C19—H19C	110.00
O16—C12—N13	124.4 (2)	H19A—C19—H19B	109.00
N13—C14—C4	107.6 (2)	H19A—C19—H19C	109.00
O15—C14—N13	126.6 (2)	H19B—C19—H19C	110.00
O15—C14—C4	125.9 (2)	C18—C20—H20A	109.00
N13—C17—C18	113.0 (2)	C18—C20—H20B	109.00
C19—C18—C20	111.2 (3)	C18—C20—H20C	110.00
C17—C18—C19	111.8 (3)	H20A—C20—H20B	109.00
C17—C18—C20	108.5 (3)	H20A—C20—H20C	110.00
S1—C2—H2A	109.00	H20B—C20—H20C	109.00
S1—C2—H2B	109.00

C10—S1—C2—C3	−37.5 (3)	N11—C4—C14—N13	0.2 (3)
C2—S1—C10—C5	7.6 (3)	C14—C4—C5—C10	146.9 (3)
C2—S1—C10—C9	−173.0 (3)	N11—C4—C5—C6	76.0 (3)
C4—N11—C12—N13	2.7 (3)	N11—C4—C5—C10	−101.9 (3)
C4—N11—C12—O16	−177.7 (3)	C3—C4—C5—C6	−157.4 (3)
C12—N11—C4—C5	−119.6 (2)	C3—C4—C5—C10	24.6 (4)
C12—N11—C4—C14	−1.8 (3)	C3—C4—C14—O15	62.5 (4)
C12—N11—C4—C3	112.8 (3)	C3—C4—C14—N13	−117.0 (3)
C17—N13—C12—O16	−0.9 (4)	C5—C4—C14—O15	−62.8 (4)
C14—N13—C12—N11	−2.6 (3)	C5—C4—C14—N13	117.8 (2)
C12—N13—C14—C4	1.4 (3)	C10—C5—C6—C7	−0.6 (5)
C14—N13—C12—O16	177.8 (3)	C4—C5—C10—S1	−1.6 (5)
C12—N13—C17—C18	−99.0 (3)	C4—C5—C6—C7	−178.6 (3)
C14—N13—C17—C18	82.5 (3)	C4—C5—C10—C9	179.0 (3)
C12—N13—C14—O15	−178.0 (3)	C6—C5—C10—S1	−179.6 (3)
C17—N13—C14—C4	−179.9 (2)	C6—C5—C10—C9	1.0 (5)
C17—N13—C12—N11	178.8 (2)	C5—C6—C7—C8	−0.2 (6)
C17—N13—C14—O15	0.7 (5)	C6—C7—C8—C9	0.4 (7)
S1—C2—C3—C4	65.3 (3)	C7—C8—C9—C10	0.1 (7)
C2—C3—C4—C5	−57.9 (4)	C8—C9—C10—C5	−0.8 (6)
C2—C3—C4—C14	178.1 (3)	C8—C9—C10—S1	179.8 (3)
C2—C3—C4—N11	68.3 (3)	N13—C17—C18—C19	61.5 (3)
C14—C4—C5—C6	−35.2 (4)	N13—C17—C18—C20	−175.6 (3)
N11—C4—C14—O15	179.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O16ⁱ	0.86	2.03	2.850 (3)	160

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O16ⁱ	0.86	2.03	2.850 (3)	160

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

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

References

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Volume 70| Part 9| September 2014| Pages o1043-o1044

doi:10.1107/S1600536814018030

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 1′-(2-methyl­prop­yl)-2,3-di­hydro­spiro­[1-benzo­thio­pyran-4,4′-imidazolidine]-2′,5′-dione

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 1′-(2-methylpropyl)-2,3-dihydrospiro[1-benzothiopyran-4,4′-imidazolidine]-2′,5′-dione