Crystal structure of 1'-(2-methyl-prop-yl)-2,3-di-hydro-spiro-[1-benzo-thio-pyran-4,4'-imidazolidine]-2',5'-dione.

In the title compound, C15H18N2O2S, the 2,3-di-hydro-1-benzo-thio-pyran 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 mol-ecules into inversion dimers.

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 ▶).

Experimental

Crystal data

C15H18N2O2S

M = 290.38

Monoclinic,

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

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

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.195

S = 1.06

2397 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.47 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814018030/xu5809sup1.cif

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

Click here for additional data file.

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

Click here for additional data file.

. DOI: 10.1107/S1600536814018030/xu5809fig1.tif

A view of the title mol­ecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814018030/xu5809fig2.tif

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

CCDC reference: 1018087

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H18N2O2S	Z = 4
Mr = 290.38	F(000) = 616
Monoclinic, P21/c	Dx = 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

Bruker X8 Proteum diffractometer	1959 reflections with I > 2σ(I)
Detector resolution: 18.4 pixels mm-1	Rint = 0.067
φ and ω scans	θmax = 64.2°, θmin = 3.8°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −15→14
Tmin = 0.747, Tmax = 0.753	k = −8→11
5024 measured reflections	l = −11→15
2397 independent reflections

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(Fo2) + (0.1345P)2 + 0.3286P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2397 reflections	Δρmax = 0.43 e Å−3
184 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .