3-(4-Chloro­phenyl­sulfon­yl)-8-methyl-1,3-diaza­spiro­[4.5]decane-2,4-dione

Kashif, M.K.; Khawar Rauf, M.; Bolte, M.; Hameed, S.

doi:10.1107/S1600536809027482

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1893

doi:10.1107/S1600536809027482

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3-(4-Chlorophenylsulfonyl)-8-methyl-1,3-diazaspiro[4.5]decane-2,4-dione

M. Kalim Kashif,^a M. Khawar Rauf,^a Michael Bolte ^b and Shahid Hameed ^a ^*

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: shameed@qau.edu.pk

(Received 9 July 2009; accepted 13 July 2009; online 18 July 2009)

In the title compound, C₁₅H₁₇ClN₂O₄S, the atoms in the hydantoin ring are coplanar (r.m.s. deviation = 0.006 Å). The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds which link the molecules into centrosymmetric dimers. The dihedral angle subtended by the 4-chlorophenyl group with the plane passing through the hydantoin unit is 82.98 (4)°. The cyclohexyl 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_r = 356.82
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.030
wR(F²) = 0.081
S = 1.04
3203 reflections
213 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.38 e Å⁻³

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) -x+1, -y+1, -z+1.

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.

Supporting information

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

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

checkCIF report

Comment top

Diabetes is one of the major causes of disease related deaths in these modern times and the people in South-east Asia and Western Pacific are being the most at risk (Tiwari et al., 2002). To cure the disease sulfonyl ureas are the most frequently used antidiabetic drugs (DeFronzo, 1999; Feinglos & Bethel, 1998). An important complication related to this disease is the cataract formation and imidazolidine-2,4-diones have been found as aldose reductase inhibitors (Murakami et al., 1997). The combination of the two scaffolds, i.e. the sulfonyl urea and the imidazolidine-2,4-dione, in one molecule may be a useful combination to cure the disease and associated complications, especially the cataract formation. With this hypothesis in mind, we synthesized a number of N-arylsulfonylimidazolidine-2,4-diones and evaluated their antidiabetic activity (Hussain et al., 2009a,b; Kashif, Ahmad et al., 2008; Kashif, Hussain et al., 2008). In the present paper, we report the synthesis and crystal structure of the title compound. The bond lengths and angles within the hydantoin (2,4-imidazolidenedione) moiety are normal, typical of those observed in cyclohexanespiro-5'-hydantoin (Gauthier et al., 1997; Kashif & Hussain et al., 2008). The hydantoin unit is exactly planar (r.m.s. deviation 0.006 Å). The cyclohexane ring has adopted chair conformation, with endocyclic torsion-angle magnitudes of 54.87 (16)–56.26 (16)°. The C1—O3 and C3—O4 bond lengths are 1.1985 (17) and 1.2242 (16) Å, respectively, which are close to the standard value for CO(1.20 Å). The dihedral angle subtended by the p-chlorophenyl group with the plane passing through the hydantoin moiety is 82.98 (4)°. Intermolecular N—H···O hydrogen bonds link the molecules to form centrosymmetric dimers.

Related literature top

For background to diabetes and its treatmnent, see: Tiwari et al. (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 top

Substituted cyclohexanone (0.1 mol) and ammonium carbonate (0.6 mol) were placed in a 100 ml round bottom flask. Potassium cyanide (0.1 mol) was dissolved in aqueous ethanol (60%) and added to the reaction flask. The mixture was heated on an oil bath at 328–333 K until the reaction was complete (monitored by TLC). After cooling to room temperature, the reaction mixture was concentrated and acidified using conc. HCl. The resulting precipitates were filtered, dissolved in saturated NaOH_(aq) solution and extracted with diethyl ether (2 × 25 ml). The aqueous layer was acidified to precipitate 8-substituted-1,3-diazaspiro[4.5]decane-2,4-dione, which was filtered and recrystallized from ethanol/water. 8-substituted-1,3-diazaspiro[4.5]decane-2,4-dione (4.8 mmol) in CH₂Cl₂ (20 ml) was stirred with triethyl amine (4.8 mmol) and catalytic amounts of DMAP. The aryl sulfonyl chloride (5.8 mmol) in CH₂Cl₂ (10 ml) was added drop wise and the reaction mixture stirred at room temperature. After completion of the reaction (TLC), the mixture was diluted with 1 M HCl (20 ml) and extracted with CH₂Cl₂ (3 × 25 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Recrystallization of the residue from ethyl acetate afforded the colourless plate-like crystals, suitable for X-ray analysis.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound with displacement ellipsoids at the 50% probability level showing atom-labelling scheme.
	Fig. 2. Partial packing diagram of (I) with view onto the ac plane. Hydrogen bonds shown as dashed lines.

3-(4-Chlorophenylsulfonyl)-8-methyl-1,3-diazaspiro[4.5]decane-2,4-dione top

Crystal data top

C₁₅H₁₇ClN₂O₄S	F(000) = 744
M_r = 356.82	D_x = 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

Data collection top

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

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)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.081	w = 1/[σ²(F_o²) + (0.038P)² + 0.7834P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3203 reflections	Δρ_max = 0.33 e Å⁻³
213 parameters	Δρ_min = −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)

Crystal data top

C₁₅H₁₇ClN₂O₄S	V = 1625.80 (18) Å³
M_r = 356.82	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.1722 (4) Å	µ = 0.38 mm⁻¹
b = 17.4561 (12) Å	T = 173 K
c = 15.1355 (9) Å	0.38 × 0.36 × 0.33 mm
β = 94.460 (5)°

Data collection top

Stoe IPDS-II two-circle diffractometer	3203 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	2983 reflections with I > 2σ(I)
T_min = 0.868, T_max = 0.884	R_int = 0.040
19365 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.33 e Å⁻³
3203 reflections	Δρ_min = −0.38 e Å⁻³
213 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇ClN₂O₄S
M_r	356.82
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	6.1722 (4), 17.4561 (12), 15.1355 (9)
β (°)	94.460 (5)
V (Å³)	1625.80 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.38 × 0.36 × 0.33

Data collection
Diffractometer	Stoe IPDS-II two-circle diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2009; Blessing, 1995)
T_min, T_max	0.868, 0.884
No. of measured, independent and observed [I > 2σ(I)] reflections	19365, 3203, 2983
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.081, 1.04
No. of reflections	3203
No. of parameters	213
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.38

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Acknowledgements

MKR is grateful to the HEC-Pakistan for financial support for a PhD program under scholarship No. [ILC–0363104].

References

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