3-(4-Chloro-phenyl-sulfon-yl)-8-methyl-1,3-diaza-spiro-[4.5]decane-2,4-dione.

In the title compound, C(15)H(17)ClN(2)O(4)S, the atoms in the hydantoin ring are coplanar (r.m.s. deviation = 0.006 Å). The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds which link the mol-ecules into centrosymmetric dimers. The dihedral angle subtended by the 4-chloro-phenyl group with the plane passing through the hydantoin unit is 82.98 (4)°. The cyclo-hexyl ring adopts an ideal chair conformation.

Related literature

For background to diabetes and its treatment, see: Tiwari & Rao (2002 ▶); DeFronzo (1999 ▶); Feinglos & Bethel (1998 ▶); Murakami et al., (1997 ▶). We have synthesized a number of N-aryl­sulfonyl­imidazolidine-2,4-diones and evaluated their anti­diabetic activity, see: Hussain et al. (2009a ▶,b ▶); Kashif, Ahmad et al. (2008 ▶); Kashif, Hussain et al. (2008 ▶); For related structures, see: Gauthier et al. (1997 ▶); Kashif, Hussain et al. (2008 ▶).

Experimental

Crystal data

C15H17ClN2O4S

M = 356.82

Monoclinic,

a = 6.1722 (4) Å

b = 17.4561 (12) Å

c = 15.1355 (9) Å

β = 94.460 (5)°

V = 1625.80 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 173 K

0.38 × 0.36 × 0.33 mm

Data collection

Stoe IPDS-II two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T min = 0.868, T max = 0.884

19365 measured reflections

3203 independent reflections

2983 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.081

S = 1.04

3203 reflections

213 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.38 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027482/hg2537sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027482/hg2537Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H17ClN2O4S	F(000) = 744
Mr = 356.82	Dx = 1.458 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15156 reflections
a = 6.1722 (4) Å	θ = 3.0–26.3°
b = 17.4561 (12) Å	µ = 0.38 mm−1
c = 15.1355 (9) Å	T = 173 K
β = 94.460 (5)°	Block, colourless
V = 1625.80 (18) Å3	0.38 × 0.36 × 0.33 mm
Z = 4

Stoe IPDS-II two-circle diffractometer	3203 independent reflections
Radiation source: fine-focus sealed tube	2983 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω scans	θmax = 26.0°, θmin = 2.9°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −7→7
Tmin = 0.868, Tmax = 0.884	k = −21→21
19365 measured reflections	l = −16→18

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)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.038P)2 + 0.7834P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3203 reflections	Δρmax = 0.33 e Å−3
213 parameters	Δρmin = −0.38 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: 0.0255 (15)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.

	x	y	z	Uiso*/Ueq
S1	0.36511 (5)	0.371795 (19)	0.23107 (2)	0.02303 (12)
Cl1	0.79176 (9)	0.63621 (3)	0.02791 (3)	0.05300 (16)
N1	0.50643 (18)	0.37056 (6)	0.33214 (7)	0.0219 (2)
N2	0.62920 (18)	0.41517 (6)	0.46472 (7)	0.0220 (2)
H2	0.641 (3)	0.4423 (11)	0.5109 (14)	0.042 (5)*
O1	0.14563 (16)	0.39092 (7)	0.24485 (7)	0.0341 (3)
O2	0.41742 (18)	0.30140 (6)	0.19042 (7)	0.0313 (2)
O3	0.7072 (2)	0.25599 (6)	0.33154 (7)	0.0384 (3)
O4	0.37659 (16)	0.48815 (6)	0.38160 (6)	0.0289 (2)
C1	0.6589 (2)	0.31459 (8)	0.36628 (9)	0.0234 (3)
C2	0.7484 (2)	0.34352 (7)	0.45728 (8)	0.0200 (3)
C3	0.4938 (2)	0.43204 (7)	0.39448 (8)	0.0212 (3)
C4	0.9937 (2)	0.35863 (9)	0.45695 (9)	0.0277 (3)
H4A	1.0689	0.3109	0.4417	0.033*
H4B	1.0202	0.3976	0.4115	0.033*
C5	1.0850 (2)	0.38688 (9)	0.54830 (10)	0.0303 (3)
H5A	1.2440	0.3940	0.5478	0.036*
H5B	1.0198	0.4372	0.5605	0.036*
C6	1.0389 (2)	0.33104 (9)	0.62226 (10)	0.0313 (3)
H6	1.1136	0.2816	0.6107	0.038*
C7	0.7954 (3)	0.31502 (9)	0.62127 (9)	0.0302 (3)
H7A	0.7193	0.3625	0.6368	0.036*
H7B	0.7699	0.2760	0.6668	0.036*
C8	0.7004 (2)	0.28651 (8)	0.53063 (9)	0.0284 (3)
H8A	0.5413	0.2800	0.5317	0.034*
H8B	0.7641	0.2360	0.5179	0.034*
C9	1.1307 (3)	0.36103 (12)	0.71245 (12)	0.0472 (4)
H9A	1.2869	0.3704	0.7109	0.071*
H9B	1.1067	0.3229	0.7583	0.071*
H9C	1.0573	0.4089	0.7260	0.071*
C11	0.4850 (2)	0.44792 (8)	0.17624 (8)	0.0228 (3)
C12	0.6817 (2)	0.43427 (8)	0.13975 (9)	0.0286 (3)
H12	0.7502	0.3856	0.1460	0.034*
C13	0.7761 (2)	0.49288 (10)	0.09407 (10)	0.0340 (3)
H13	0.9109	0.4851	0.0691	0.041*
C14	0.6711 (3)	0.56299 (9)	0.08531 (9)	0.0332 (3)
C15	0.4758 (3)	0.57708 (9)	0.12184 (10)	0.0352 (3)
H15	0.4075	0.6257	0.1152	0.042*
C16	0.3816 (2)	0.51863 (8)	0.16838 (10)	0.0295 (3)
H16	0.2484	0.5269	0.1944	0.035*

	U11	U22	U33	U12	U13	U23
S1	0.02463 (19)	0.02646 (19)	0.01742 (17)	−0.00340 (12)	−0.00210 (12)	−0.00176 (12)
Cl1	0.0750 (3)	0.0439 (3)	0.0392 (2)	−0.0247 (2)	−0.0012 (2)	0.01235 (18)
N1	0.0264 (6)	0.0221 (6)	0.0168 (5)	0.0020 (4)	−0.0016 (4)	−0.0026 (4)
N2	0.0249 (6)	0.0227 (6)	0.0179 (5)	0.0060 (4)	−0.0015 (4)	−0.0051 (4)
O1	0.0235 (5)	0.0503 (7)	0.0281 (5)	−0.0030 (5)	−0.0013 (4)	0.0017 (5)
O2	0.0438 (6)	0.0258 (5)	0.0233 (5)	−0.0057 (4)	−0.0036 (4)	−0.0056 (4)
O3	0.0607 (7)	0.0273 (5)	0.0261 (5)	0.0145 (5)	−0.0041 (5)	−0.0077 (4)
O4	0.0328 (5)	0.0288 (5)	0.0241 (5)	0.0120 (4)	−0.0042 (4)	−0.0049 (4)
C1	0.0301 (7)	0.0215 (7)	0.0187 (6)	0.0018 (5)	0.0021 (5)	0.0001 (5)
C2	0.0242 (6)	0.0185 (6)	0.0173 (6)	0.0032 (5)	0.0017 (5)	−0.0010 (5)
C3	0.0215 (6)	0.0236 (6)	0.0186 (6)	0.0005 (5)	0.0019 (5)	−0.0032 (5)
C4	0.0232 (7)	0.0355 (8)	0.0250 (7)	0.0049 (6)	0.0062 (5)	0.0005 (6)
C5	0.0192 (6)	0.0401 (8)	0.0314 (8)	−0.0007 (6)	0.0011 (5)	−0.0038 (6)
C6	0.0346 (8)	0.0340 (8)	0.0239 (7)	0.0101 (6)	−0.0063 (6)	−0.0037 (6)
C7	0.0417 (8)	0.0309 (8)	0.0178 (6)	−0.0053 (6)	0.0005 (6)	0.0042 (5)
C8	0.0377 (8)	0.0253 (7)	0.0218 (7)	−0.0070 (6)	−0.0008 (6)	0.0038 (5)
C9	0.0475 (10)	0.0605 (11)	0.0313 (9)	0.0052 (8)	−0.0122 (7)	−0.0098 (8)
C11	0.0258 (6)	0.0246 (6)	0.0171 (6)	−0.0014 (5)	−0.0033 (5)	−0.0012 (5)
C12	0.0291 (7)	0.0298 (7)	0.0266 (7)	0.0025 (6)	0.0008 (6)	0.0016 (6)
C13	0.0325 (8)	0.0411 (9)	0.0286 (8)	−0.0050 (6)	0.0035 (6)	0.0022 (6)
C14	0.0457 (9)	0.0315 (8)	0.0210 (7)	−0.0122 (6)	−0.0068 (6)	0.0032 (6)
C15	0.0470 (9)	0.0254 (7)	0.0313 (8)	0.0018 (6)	−0.0079 (7)	0.0004 (6)
C16	0.0316 (7)	0.0301 (7)	0.0263 (7)	0.0044 (6)	−0.0023 (6)	−0.0029 (6)

S1—O2	1.4225 (11)	C6—C7	1.528 (2)
S1—O1	1.4262 (11)	C6—C9	1.529 (2)
S1—N1	1.7011 (11)	C6—H6	1.0000
S1—C11	1.7602 (14)	C7—C8	1.5325 (19)
Cl1—C14	1.7447 (15)	C7—H7A	0.9900
N1—C1	1.4251 (17)	C7—H7B	0.9900
N1—C3	1.4352 (16)	C8—H8A	0.9900
N2—C3	1.3331 (17)	C8—H8B	0.9900
N2—C2	1.4599 (16)	C9—H9A	0.9800
N2—H2	0.84 (2)	C9—H9B	0.9800
O3—C1	1.1985 (17)	C9—H9C	0.9800
O4—C3	1.2242 (16)	C11—C16	1.390 (2)
C1—C2	1.5294 (18)	C11—C12	1.393 (2)
C2—C8	1.5369 (18)	C12—C13	1.388 (2)
C2—C4	1.5373 (18)	C12—H12	0.9500
C4—C5	1.533 (2)	C13—C14	1.386 (2)
C4—H4A	0.9900	C13—H13	0.9500
C4—H4B	0.9900	C14—C15	1.387 (2)
C5—C6	1.528 (2)	C15—C16	1.393 (2)
C5—H5A	0.9900	C15—H15	0.9500
C5—H5B	0.9900	C16—H16	0.9500
O2—S1—O1	121.04 (7)	C5—C6—H6	107.9
O2—S1—N1	105.08 (6)	C7—C6—H6	107.9
O1—S1—N1	107.33 (6)	C9—C6—H6	107.9
O2—S1—C11	109.29 (6)	C6—C7—C8	112.07 (12)
O1—S1—C11	109.35 (7)	C6—C7—H7A	109.2
N1—S1—C11	103.21 (6)	C8—C7—H7A	109.2
C1—N1—C3	110.02 (10)	C6—C7—H7B	109.2
C1—N1—S1	127.78 (9)	C8—C7—H7B	109.2
C3—N1—S1	122.10 (9)	H7A—C7—H7B	107.9
C3—N2—C2	114.60 (11)	C7—C8—C2	110.76 (11)
C3—N2—H2	123.2 (13)	C7—C8—H8A	109.5
C2—N2—H2	122.2 (13)	C2—C8—H8A	109.5
O3—C1—N1	127.29 (12)	C7—C8—H8B	109.5
O3—C1—C2	126.30 (12)	C2—C8—H8B	109.5
N1—C1—C2	106.40 (10)	H8A—C8—H8B	108.1
N2—C2—C1	101.73 (10)	C6—C9—H9A	109.5
N2—C2—C8	111.87 (11)	C6—C9—H9B	109.5
C1—C2—C8	111.12 (11)	H9A—C9—H9B	109.5
N2—C2—C4	110.84 (11)	C6—C9—H9C	109.5
C1—C2—C4	109.93 (11)	H9A—C9—H9C	109.5
C8—C2—C4	111.02 (11)	H9B—C9—H9C	109.5
O4—C3—N2	129.04 (12)	C16—C11—C12	121.78 (13)
O4—C3—N1	123.73 (12)	C16—C11—S1	120.22 (11)
N2—C3—N1	107.24 (11)	C12—C11—S1	117.98 (11)
C5—C4—C2	110.19 (11)	C13—C12—C11	118.93 (14)
C5—C4—H4A	109.6	C13—C12—H12	120.5
C2—C4—H4A	109.6	C11—C12—H12	120.5
C5—C4—H4B	109.6	C14—C13—C12	119.16 (14)
C2—C4—H4B	109.6	C14—C13—H13	120.4
H4A—C4—H4B	108.1	C12—C13—H13	120.4
C6—C5—C4	112.28 (12)	C13—C14—C15	122.20 (14)
C6—C5—H5A	109.1	C13—C14—Cl1	118.69 (13)
C4—C5—H5A	109.1	C15—C14—Cl1	119.11 (12)
C6—C5—H5B	109.1	C14—C15—C16	118.80 (14)
C4—C5—H5B	109.1	C14—C15—H15	120.6
H5A—C5—H5B	107.9	C16—C15—H15	120.6
C5—C6—C7	110.42 (11)	C11—C16—C15	119.12 (14)
C5—C6—C9	111.01 (14)	C11—C16—H16	120.4
C7—C6—C9	111.56 (13)	C15—C16—H16	120.4
O2—S1—N1—C1	4.87 (13)	C8—C2—C4—C5	−56.08 (15)
O1—S1—N1—C1	134.92 (12)	C2—C4—C5—C6	56.26 (16)
C11—S1—N1—C1	−109.63 (12)	C4—C5—C6—C7	−55.42 (16)
O2—S1—N1—C3	−179.06 (10)	C4—C5—C6—C9	−179.68 (13)
O1—S1—N1—C3	−49.01 (12)	C5—C6—C7—C8	54.87 (16)
C11—S1—N1—C3	66.44 (11)	C9—C6—C7—C8	178.81 (13)
C3—N1—C1—O3	179.43 (14)	C6—C7—C8—C2	−55.61 (16)
S1—N1—C1—O3	−4.1 (2)	N2—C2—C8—C7	−68.41 (15)
C3—N1—C1—C2	0.01 (14)	C1—C2—C8—C7	178.65 (12)
S1—N1—C1—C2	176.48 (9)	C4—C2—C8—C7	55.99 (15)
C3—N2—C2—C1	−1.17 (14)	O2—S1—C11—C16	146.70 (11)
C3—N2—C2—C8	−119.84 (12)	O1—S1—C11—C16	12.12 (13)
C3—N2—C2—C4	115.67 (12)	N1—S1—C11—C16	−101.87 (11)
O3—C1—C2—N2	−178.79 (14)	O2—S1—C11—C12	−31.78 (12)
N1—C1—C2—N2	0.63 (13)	O1—S1—C11—C12	−166.36 (11)
O3—C1—C2—C8	−59.59 (19)	N1—S1—C11—C12	79.64 (11)
N1—C1—C2—C8	119.83 (12)	C16—C11—C12—C13	−0.2 (2)
O3—C1—C2—C4	63.71 (18)	S1—C11—C12—C13	178.21 (11)
N1—C1—C2—C4	−116.87 (12)	C11—C12—C13—C14	−0.6 (2)
C2—N2—C3—O4	−178.83 (13)	C12—C13—C14—C15	1.0 (2)
C2—N2—C3—N1	1.22 (15)	C12—C13—C14—Cl1	179.88 (11)
C1—N1—C3—O4	179.32 (13)	C13—C14—C15—C16	−0.4 (2)
S1—N1—C3—O4	2.62 (18)	Cl1—C14—C15—C16	−179.32 (11)
C1—N1—C3—N2	−0.73 (14)	C12—C11—C16—C15	0.8 (2)
S1—N1—C3—N2	−177.43 (9)	S1—C11—C16—C15	−177.62 (11)
N2—C2—C4—C5	68.89 (14)	C14—C15—C16—C11	−0.5 (2)
C1—C2—C4—C5	−179.43 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4i	0.84 (2)	2.04 (2)	2.8763 (15)	171.5 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4i	0.84 (2)	2.04 (2)	2.8763 (15)	171.5 (19)

Symmetry code: (i) .