2-(4-Chloro­phen­yl)-1,5-diphenyl-3-tosyl­imidazolidin-4-one

Ranjith, S.; SubbiahPandi, A.; Namitharan, K.; Pitchumani, K.

doi:10.1107/S1600536811008427

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o843

doi:10.1107/S1600536811008427

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2-(4-Chlorophenyl)-1,5-diphenyl-3-tosylimidazolidin-4-one

S. Ranjith,^a A. SubbiahPandi,^a ^* K. Namitharan ^b and K. Pitchumani ^b

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bSchool of Chemistry, Madurai Kamaraj University, Madurai 625 021, India
^*Correspondence e-mail: a_sp59@yahoo.in

(Received 13 January 2011; accepted 5 March 2011; online 12 March 2011)

In the title compound, C₂₈H₂₃ClN₂O₃S, the central imidazolidine ring adopts a twisted conformation and the S atom has distorted tetrahedral geometry. The crystal packing is stabilized by C—H⋯O, C—H⋯π and π–π interactions [centroid–centroid distance = 3.8302 (10) Å].

Related literature

For the biological activity of sulfonamides, see: Zareef et al. (2007 ); Chohan et al. (2007 ); Pomarnacka & Kozlarska-Kedra (2003 ); Nieto et al. (2005 ); Wang et al. (1995 ). For a related structure, see: Chakkaravarthi et al. (2008 ). For puckering parameters, see: Cremer & Pople (1975 ). For asymmetry parameters, see: Nardelli et al. (1983 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₈H₂₃ClN₂O₃S
M_r = 503.00
Monoclinic, P 2₁ /n
a = 10.8458 (3) Å
b = 13.0191 (4) Å
c = 17.6720 (5) Å
β = 103.757 (2)°
V = 2423.75 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.981, T_max = 0.985
32315 measured reflections
7313 independent reflections
5098 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.115
S = 1.05
7313 reflections
317 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the C2–C7 and C15–C20 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O3ⁱ	0.98	2.44	3.3659 (17)	158
C14—H14⋯O3ⁱ	0.93	2.57	3.3855 (19)	146
C24—H24⋯O2ⁱⁱ	0.93	2.59	3.289 (2)	132
C1—H1C⋯Cg4ⁱⁱⁱ	0.96	2.90	3.484 (2)	120
C11—H11⋯Cg2ⁱⁱⁱ	0.93	2.88	3.619 (17)	138
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008427/pk2300sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008427/pk2300Isup2.hkl

checkCIF report

Comment top

Sulfonamides have widely been recognized for their wide variety of pharmacological activities such as antibacterial, antitumor, anti-carbonic anhydrase, diuretic, hypoglycaemic, antithyroid and protease inhibitory activity. Sulfonamides have also been used clinically as antimalarial agents (Zareef et al., 2007), particularly sulfadiazine and sulfadoxine. Due to their significant pharmacology applications and widespread use in medicine, these compounds have also gained attention in bioinorganic and metal-based (Chohan et al., 2007) drug chemistry. Sulfonamide derivatives are well known drugs and are used to control diseases caused by bacterial infections. Benzene sulfonamide derivatives are known to exhibit anticancer and HIV activities (Pomarnacka & Kozlarska-Kedra, 2003) and antibacterial activities (Nieto et al., 2005). Imidazolidine compounds are important intermediates and building blocks in the construction of various biologically active compounds (Wang et al., 1995). Against this background, and in order to obtain detailed information on molecular conformations in the solid state, an X-ray study of the title compound was carried out.

X-ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The geometry around the S atom is distorted tetrahedral, comprising two O atoms of the sulfonyl group, a C atom of a benzene ring and the imidazolidine N atom. The S–O, S–C, and S–N distances are 1.418 (1), 1.747 (1) and 1.677 (1) Å, respectively. These are comparable to those in similar structures (Chakkaravarthi et al., 2008). The atom Cl1 deviates by 0.130 (1)Å from the least-squares plane of the ring C9–C14. The S atom exhibits significant deviation from that of a regular tetrahedron, with the largest deviations for the O–S–O [O1–S1–O2 120.9 (7)°] and O–S–N angles [O1–S1–N1 106.5 (6)°]. The widening of the angles may be due to repulsive interactions between the two short S=O bonds, similar to what is observed in related structures (Chakkaravarthi et al., 2008). The chlorobenzene ring makes the dihedral angles of 39.4 (8), 85.1 (8) and 1.9 (9)° with respect to the C2–C7, C15–C20 and C23–C28 benzene rings.

The imidazolidine ring adopts a twisted conformation, with puckering parameters q₂ and ϕ (Cremer & Pople, 1975) and the smallest displacement asymmetric parameters, Δ, (Nardelli et al., 1983) as follows: q₂ = 0.1300 (14) Å, ϕ = 21.9 (6)°, Δ_s(C8) = 4.70 (15). The intramolecular C6–H6···O2 hydrogen bond completes a five-membered ring, which generates an S(5) motif (Bernstein et al., 1995). Atoms C8 and C14 act as donors to form bifurcated hydrogen bonds with atom O3 as an acceptor, results in the formation of R²₁(6) bifurcated ring. In addition to van der Waals interactions, the crystal packing is stabilized by C–H..O, C–H···π and π···π interactions (Table. 1).

Related literature top

For the biological activity of sulfonamides, see: Zareef et al. (2007); Chohan et al. (2007); Pomarnacka & Kozlarska-Kedra (2003); Nieto et al. (2005); Wang et al. (1995). For a related structure, see: Chakkaravarthi et al. (2008). For puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Nardelli et al. (1983). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

4-Toluenesulfonyl azide (1.3 mmol), phenylacetylene (1.2 mmol), 4-chlorophenyl N-phenylnitrone (1.0 mmol) and triethylamine (2 mmol) were successively added to Cu¹—Y zeolite (30 mg) in dichloromethane under N₂ atmosphere. After stirring at room temperature for 6 h, the mixture was diluted with dichloromethane. After removing the catalyst by filtration, followed by solvent evaporation, the resulting crude product was finally purified by column chromatography (silica gel). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in acetone at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The structure of the title compound showing the atom-numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. π—π, C–H···π interactions (dotted lines) in the title compound and also bifurcated hydrogen bonds formed by C8–H8···O3 and C14–H14···O3 at 3/2 - x,-1/2 + y,1/2 - z, results in the formation of R²₁(6) [O3,H8,C8,C9,C14,H14] bifurcated ring. Cg denotes ring centroid.[Symmetry code: (i) 2 - x,1 - y,-z;(ii) 1 - x,1 - y,-z; (iii) 3/2 - x,-1/2 + y,1/2 - z.]

2-(4-Chlorophenyl)-1,5-diphenyl-3-tosylimidazolidin-4-one top

Crystal data top

C₂₈H₂₃ClN₂O₃S	F(000) = 1048
M_r = 503.00	D_x = 1.378 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7313 reflections
a = 10.8458 (3) Å	θ = 2.4–30.4°
b = 13.0191 (4) Å	µ = 0.28 mm⁻¹
c = 17.6720 (5) Å	T = 293 K
β = 103.757 (2)°	Block, colourless
V = 2423.75 (12) Å³	0.25 × 0.22 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	7313 independent reflections
Radiation source: fine-focus sealed tube	5098 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω and ϕ scans	θ_max = 30.4°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.981, T_max = 0.985	k = −17→18
32315 measured reflections	l = −22→25

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0495P)² + 0.5408P] where P = (F_o² + 2F_c²)/3
7313 reflections	(Δ/σ)_max = 0.001
317 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₈H₂₃ClN₂O₃S	V = 2423.75 (12) Å³
M_r = 503.00	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.8458 (3) Å	µ = 0.28 mm⁻¹
b = 13.0191 (4) Å	T = 293 K
c = 17.6720 (5) Å	0.25 × 0.22 × 0.19 mm
β = 103.757 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	7313 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5098 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.985	R_int = 0.030
32315 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.05	Δρ_max = 0.28 e Å⁻³
7313 reflections	Δρ_min = −0.35 e Å⁻³
317 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
C1	0.8204 (2)	0.6211 (2)	−0.10561 (13)	0.0944 (10)
H1A	0.8293	0.5757	−0.1468	0.142*
H1B	0.8843	0.6735	−0.0987	0.142*
H1C	0.7378	0.6523	−0.1188	0.142*
C2	0.83550 (16)	0.5610 (2)	−0.03116 (10)	0.0615 (6)
C3	0.87311 (18)	0.60888 (16)	0.03995 (11)	0.0592 (5)
H3	0.8903	0.6789	0.0417	0.071*
C4	0.88600 (16)	0.55548 (13)	0.10884 (10)	0.0477 (4)
H4	0.9107	0.5892	0.1565	0.057*
C5	0.86169 (13)	0.45127 (12)	0.10598 (8)	0.0370 (3)
C6	0.82418 (16)	0.40127 (16)	0.03542 (10)	0.0524 (4)
H6	0.8079	0.3311	0.0334	0.063*
C7	0.81134 (17)	0.4579 (2)	−0.03242 (10)	0.0649 (6)
H7	0.7855	0.4248	−0.0802	0.078*
C8	0.65428 (12)	0.31035 (10)	0.20980 (7)	0.0301 (3)
H8	0.6929	0.2445	0.2291	0.036*
C9	0.58939 (12)	0.30175 (10)	0.12399 (8)	0.0298 (3)
C10	0.51246 (13)	0.37975 (11)	0.08615 (8)	0.0359 (3)
H10	0.4942	0.4355	0.1145	0.043*
C11	0.46242 (14)	0.37599 (12)	0.00672 (9)	0.0396 (3)
H11	0.4102	0.4284	−0.0184	0.048*
C12	0.49087 (14)	0.29372 (12)	−0.03472 (8)	0.0398 (3)
C13	0.56268 (16)	0.21323 (13)	0.00174 (9)	0.0455 (4)
H13	0.5782	0.1566	−0.0268	0.055*
C14	0.61182 (14)	0.21732 (11)	0.08156 (9)	0.0389 (3)
H14	0.6602	0.1629	0.1068	0.047*
C15	0.46241 (13)	0.29610 (11)	0.26339 (8)	0.0336 (3)
C16	0.43733 (14)	0.19730 (12)	0.23351 (9)	0.0388 (3)
H16	0.4952	0.1644	0.2104	0.047*
C17	0.32626 (16)	0.14799 (14)	0.23816 (10)	0.0491 (4)
H17	0.3105	0.0818	0.2185	0.059*
C18	0.23885 (16)	0.19555 (16)	0.27141 (11)	0.0551 (5)
H18	0.1638	0.1623	0.2735	0.066*
C19	0.26360 (15)	0.29236 (15)	0.30142 (10)	0.0516 (4)
H19	0.2050	0.3246	0.3242	0.062*
C20	0.37404 (14)	0.34271 (13)	0.29837 (9)	0.0429 (3)
H20	0.3898	0.4081	0.3197	0.052*
C21	0.60120 (14)	0.45092 (11)	0.28719 (8)	0.0353 (3)
H21	0.5306	0.4961	0.2630	0.042*
C23	0.63258 (14)	0.46406 (11)	0.37521 (8)	0.0364 (3)
C28	0.70564 (19)	0.39176 (15)	0.42268 (10)	0.0578 (5)
H28	0.7302	0.3321	0.4013	0.069*
C27	0.7424 (2)	0.40811 (19)	0.50230 (11)	0.0731 (6)
H27	0.7914	0.3593	0.5344	0.088*
C26	0.7067 (2)	0.49587 (19)	0.53377 (11)	0.0694 (6)
H26	0.7324	0.5070	0.5872	0.083*
C25	0.6339 (2)	0.56698 (16)	0.48732 (11)	0.0628 (5)
H25	0.6089	0.6261	0.5092	0.075*
C24	0.59660 (18)	0.55168 (13)	0.40753 (10)	0.0491 (4)
H24	0.5472	0.6007	0.3759	0.059*
N1	0.75179 (11)	0.39178 (9)	0.22299 (6)	0.0318 (2)
N2	0.57393 (11)	0.34697 (10)	0.25969 (7)	0.0368 (3)
O1	0.98232 (10)	0.43180 (9)	0.25004 (6)	0.0459 (3)
O2	0.89588 (10)	0.27584 (9)	0.17703 (7)	0.0479 (3)
C22	0.71777 (14)	0.47825 (11)	0.25818 (8)	0.0350 (3)
S1	0.88693 (3)	0.38196 (3)	0.19302 (2)	0.03485 (10)
Cl1	0.43640 (5)	0.29404 (4)	−0.13549 (2)	0.06360 (15)
O3	0.77172 (11)	0.55951 (8)	0.26593 (7)	0.0480 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0684 (13)	0.165 (3)	0.0561 (13)	0.0392 (16)	0.0268 (11)	0.0549 (15)
C2	0.0390 (9)	0.1076 (17)	0.0414 (10)	0.0192 (10)	0.0163 (7)	0.0250 (10)
C3	0.0596 (11)	0.0658 (12)	0.0559 (11)	0.0111 (9)	0.0209 (9)	0.0236 (9)
C4	0.0540 (9)	0.0509 (9)	0.0390 (8)	−0.0006 (8)	0.0131 (7)	0.0051 (7)
C5	0.0329 (7)	0.0504 (9)	0.0292 (7)	−0.0002 (6)	0.0099 (5)	0.0016 (6)
C6	0.0496 (9)	0.0714 (12)	0.0382 (8)	−0.0063 (8)	0.0148 (7)	−0.0099 (8)
C7	0.0507 (10)	0.1166 (19)	0.0283 (8)	0.0025 (11)	0.0110 (7)	−0.0052 (10)
C8	0.0323 (6)	0.0316 (7)	0.0269 (6)	−0.0013 (5)	0.0078 (5)	−0.0011 (5)
C9	0.0304 (6)	0.0323 (7)	0.0273 (6)	−0.0012 (5)	0.0081 (5)	−0.0016 (5)
C10	0.0387 (7)	0.0351 (7)	0.0338 (7)	0.0041 (6)	0.0087 (6)	−0.0029 (6)
C11	0.0372 (7)	0.0431 (8)	0.0359 (7)	0.0017 (6)	0.0033 (6)	0.0054 (6)
C12	0.0383 (7)	0.0527 (9)	0.0267 (7)	−0.0074 (7)	0.0041 (6)	−0.0027 (6)
C13	0.0533 (9)	0.0458 (9)	0.0369 (8)	0.0005 (7)	0.0097 (7)	−0.0129 (7)
C14	0.0440 (8)	0.0370 (8)	0.0343 (7)	0.0054 (6)	0.0067 (6)	−0.0031 (6)
C15	0.0331 (7)	0.0423 (8)	0.0247 (6)	−0.0014 (6)	0.0057 (5)	0.0036 (5)
C16	0.0390 (7)	0.0424 (8)	0.0338 (7)	−0.0032 (6)	0.0067 (6)	0.0011 (6)
C17	0.0489 (9)	0.0514 (9)	0.0452 (9)	−0.0129 (8)	0.0076 (7)	0.0015 (7)
C18	0.0379 (8)	0.0745 (13)	0.0525 (10)	−0.0143 (8)	0.0098 (7)	0.0071 (9)
C19	0.0374 (8)	0.0731 (12)	0.0467 (9)	0.0013 (8)	0.0149 (7)	0.0025 (8)
C20	0.0408 (8)	0.0524 (9)	0.0372 (8)	0.0006 (7)	0.0123 (6)	−0.0024 (7)
C21	0.0404 (7)	0.0353 (7)	0.0313 (7)	0.0007 (6)	0.0106 (6)	−0.0028 (6)
C23	0.0420 (7)	0.0387 (7)	0.0314 (7)	−0.0048 (6)	0.0144 (6)	−0.0054 (6)
C28	0.0711 (12)	0.0630 (11)	0.0390 (9)	0.0181 (9)	0.0122 (8)	−0.0029 (8)
C27	0.0816 (14)	0.0961 (16)	0.0380 (10)	0.0180 (13)	0.0067 (10)	0.0061 (10)
C26	0.0871 (15)	0.0886 (15)	0.0351 (9)	−0.0171 (12)	0.0198 (10)	−0.0148 (10)
C25	0.0907 (14)	0.0578 (11)	0.0477 (10)	−0.0143 (11)	0.0320 (10)	−0.0208 (9)
C24	0.0671 (11)	0.0402 (8)	0.0462 (9)	−0.0046 (8)	0.0255 (8)	−0.0058 (7)
N1	0.0336 (6)	0.0333 (6)	0.0298 (6)	−0.0039 (5)	0.0101 (5)	−0.0039 (5)
N2	0.0402 (6)	0.0400 (6)	0.0341 (6)	−0.0072 (5)	0.0165 (5)	−0.0096 (5)
O1	0.0361 (5)	0.0592 (7)	0.0382 (6)	−0.0085 (5)	0.0003 (4)	0.0051 (5)
O2	0.0454 (6)	0.0413 (6)	0.0606 (7)	0.0060 (5)	0.0200 (6)	−0.0006 (5)
C22	0.0427 (7)	0.0357 (7)	0.0269 (6)	−0.0005 (6)	0.0088 (6)	−0.0004 (5)
S1	0.03133 (17)	0.0400 (2)	0.03336 (18)	0.00022 (14)	0.00796 (13)	0.00157 (14)
Cl1	0.0700 (3)	0.0859 (4)	0.02902 (19)	−0.0131 (3)	0.00031 (19)	−0.0035 (2)
O3	0.0615 (7)	0.0359 (6)	0.0511 (7)	−0.0115 (5)	0.0225 (6)	−0.0069 (5)

Geometric parameters (Å, º) top

C1—C2	1.506 (3)	C15—N2	1.3941 (18)
C1—H1A	0.9600	C15—C20	1.397 (2)
C1—H1B	0.9600	C16—C17	1.385 (2)
C1—H1C	0.9600	C16—H16	0.9300
C2—C7	1.366 (3)	C17—C18	1.376 (3)
C2—C3	1.375 (3)	C17—H17	0.9300
C3—C4	1.380 (2)	C18—C19	1.369 (3)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.381 (2)	C19—C20	1.378 (2)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.380 (2)	C20—H20	0.9300
C5—S1	1.7478 (15)	C21—N2	1.4446 (19)
C6—C7	1.386 (3)	C21—C22	1.5154 (19)
C6—H6	0.9300	C21—C23	1.5207 (19)
C7—H7	0.9300	C21—H21	0.9800
C8—N2	1.4592 (17)	C23—C24	1.373 (2)
C8—N1	1.4764 (17)	C23—C28	1.379 (2)
C8—C9	1.5165 (18)	C28—C27	1.385 (3)
C8—H8	0.9800	C28—H28	0.9300
C9—C10	1.3817 (19)	C27—C26	1.366 (3)
C9—C14	1.3844 (19)	C27—H27	0.9300
C10—C11	1.380 (2)	C26—C25	1.359 (3)
C10—H10	0.9300	C26—H26	0.9300
C11—C12	1.373 (2)	C25—C24	1.386 (2)
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.372 (2)	C24—H24	0.9300
C12—Cl1	1.7377 (15)	N1—C22	1.3782 (18)
C13—C14	1.385 (2)	N1—S1	1.6776 (11)
C13—H13	0.9300	O1—S1	1.4181 (11)
C14—H14	0.9300	O2—S1	1.4181 (12)
C15—C16	1.393 (2)	C22—O3	1.2008 (17)

C2—C1—H1A	109.5	C15—C16—H16	120.0
C2—C1—H1B	109.5	C18—C17—C16	120.95 (17)
H1A—C1—H1B	109.5	C18—C17—H17	119.5
C2—C1—H1C	109.5	C16—C17—H17	119.5
H1A—C1—H1C	109.5	C19—C18—C17	119.23 (16)
H1B—C1—H1C	109.5	C19—C18—H18	120.4
C7—C2—C3	118.31 (17)	C17—C18—H18	120.4
C7—C2—C1	121.0 (2)	C18—C19—C20	121.00 (16)
C3—C2—C1	120.7 (2)	C18—C19—H19	119.5
C2—C3—C4	121.58 (19)	C20—C19—H19	119.5
C2—C3—H3	119.2	C19—C20—C15	120.34 (16)
C4—C3—H3	119.2	C19—C20—H20	119.8
C3—C4—C5	118.97 (17)	C15—C20—H20	119.8
C3—C4—H4	120.5	N2—C21—C22	103.10 (11)
C5—C4—H4	120.5	N2—C21—C23	115.32 (12)
C6—C5—C4	120.63 (15)	C22—C21—C23	108.53 (11)
C6—C5—S1	120.18 (13)	N2—C21—H21	109.9
C4—C5—S1	119.11 (12)	C22—C21—H21	109.9
C5—C6—C7	118.55 (19)	C23—C21—H21	109.9
C5—C6—H6	120.7	C24—C23—C28	119.54 (15)
C7—C6—H6	120.7	C24—C23—C21	120.15 (14)
C2—C7—C6	121.95 (18)	C28—C23—C21	120.13 (13)
C2—C7—H7	119.0	C23—C28—C27	119.88 (17)
C6—C7—H7	119.0	C23—C28—H28	120.1
N2—C8—N1	100.27 (10)	C27—C28—H28	120.1
N2—C8—C9	115.24 (11)	C26—C27—C28	120.1 (2)
N1—C8—C9	110.82 (10)	C26—C27—H27	120.0
N2—C8—H8	110.0	C28—C27—H27	120.0
N1—C8—H8	110.0	C25—C26—C27	120.27 (18)
C9—C8—H8	110.0	C25—C26—H26	119.9
C10—C9—C14	119.01 (13)	C27—C26—H26	119.9
C10—C9—C8	120.87 (12)	C26—C25—C24	120.25 (18)
C14—C9—C8	120.04 (12)	C26—C25—H25	119.9
C11—C10—C9	120.82 (13)	C24—C25—H25	119.9
C11—C10—H10	119.6	C23—C24—C25	119.98 (18)
C9—C10—H10	119.6	C23—C24—H24	120.0
C12—C11—C10	119.08 (14)	C25—C24—H24	120.0
C12—C11—H11	120.5	C22—N1—C8	113.53 (11)
C10—C11—H11	120.5	C22—N1—S1	123.54 (9)
C13—C12—C11	121.32 (14)	C8—N1—S1	122.84 (9)
C13—C12—Cl1	120.00 (12)	C15—N2—C21	122.66 (12)
C11—C12—Cl1	118.67 (12)	C15—N2—C8	121.51 (11)
C12—C13—C14	119.14 (14)	C21—N2—C8	113.92 (11)
C12—C13—H13	120.4	O3—C22—N1	126.55 (13)
C14—C13—H13	120.4	O3—C22—C21	126.26 (13)
C9—C14—C13	120.49 (14)	N1—C22—C21	107.17 (11)
C9—C14—H14	119.8	O1—S1—O2	120.96 (7)
C13—C14—H14	119.8	O1—S1—N1	106.58 (6)
C16—C15—N2	120.96 (13)	O2—S1—N1	104.10 (6)
C16—C15—C20	118.45 (14)	O1—S1—C5	108.92 (7)
N2—C15—C20	120.58 (14)	O2—S1—C5	109.35 (7)
C17—C16—C15	120.01 (15)	N1—S1—C5	105.82 (6)
C17—C16—H16	120.0

C7—C2—C3—C4	−0.3 (3)	C27—C26—C25—C24	−0.8 (3)
C1—C2—C3—C4	179.17 (17)	C28—C23—C24—C25	0.1 (3)
C2—C3—C4—C5	0.7 (3)	C21—C23—C24—C25	−174.97 (15)
C3—C4—C5—C6	−0.5 (2)	C26—C25—C24—C23	0.4 (3)
C3—C4—C5—S1	176.25 (13)	N2—C8—N1—C22	−14.57 (14)
C4—C5—C6—C7	−0.1 (2)	C9—C8—N1—C22	107.61 (13)
S1—C5—C6—C7	−176.75 (13)	N2—C8—N1—S1	168.83 (9)
C3—C2—C7—C6	−0.2 (3)	C9—C8—N1—S1	−69.00 (14)
C1—C2—C7—C6	−179.74 (17)	C16—C15—N2—C21	177.49 (13)
C5—C6—C7—C2	0.4 (3)	C20—C15—N2—C21	−3.5 (2)
N2—C8—C9—C10	45.41 (17)	C16—C15—N2—C8	14.2 (2)
N1—C8—C9—C10	−67.56 (15)	C20—C15—N2—C8	−166.84 (13)
N2—C8—C9—C14	−137.83 (13)	C22—C21—N2—C15	−170.26 (12)
N1—C8—C9—C14	109.21 (14)	C23—C21—N2—C15	71.64 (17)
C14—C9—C10—C11	−2.5 (2)	C22—C21—N2—C8	−5.78 (16)
C8—C9—C10—C11	174.27 (13)	C23—C21—N2—C8	−123.89 (13)
C9—C10—C11—C12	−0.5 (2)	N1—C8—N2—C15	176.67 (12)
C10—C11—C12—C13	3.2 (2)	C9—C8—N2—C15	57.67 (17)
C10—C11—C12—Cl1	−175.62 (11)	N1—C8—N2—C21	11.99 (15)
C11—C12—C13—C14	−2.8 (2)	C9—C8—N2—C21	−107.01 (14)
Cl1—C12—C13—C14	176.03 (12)	C8—N1—C22—O3	−169.50 (14)
C10—C9—C14—C13	2.9 (2)	S1—N1—C22—O3	7.1 (2)
C8—C9—C14—C13	−173.88 (13)	C8—N1—C22—C21	11.90 (15)
C12—C13—C14—C9	−0.3 (2)	S1—N1—C22—C21	−171.52 (9)
N2—C15—C16—C17	179.67 (14)	N2—C21—C22—O3	177.75 (14)
C20—C15—C16—C17	0.7 (2)	C23—C21—C22—O3	−59.49 (19)
C15—C16—C17—C18	0.6 (2)	N2—C21—C22—N1	−3.64 (15)
C16—C17—C18—C19	−1.1 (3)	C23—C21—C22—N1	119.12 (13)
C17—C18—C19—C20	0.4 (3)	C22—N1—S1—O1	38.67 (13)
C18—C19—C20—C15	0.9 (3)	C8—N1—S1—O1	−145.07 (10)
C16—C15—C20—C19	−1.4 (2)	C22—N1—S1—O2	167.58 (11)
N2—C15—C20—C19	179.58 (14)	C8—N1—S1—O2	−16.15 (12)
N2—C21—C23—C24	−145.95 (14)	C22—N1—S1—C5	−77.18 (12)
C22—C21—C23—C24	99.02 (16)	C8—N1—S1—C5	99.08 (11)
N2—C21—C23—C28	39.0 (2)	C6—C5—S1—O1	149.38 (12)
C22—C21—C23—C28	−76.01 (18)	C4—C5—S1—O1	−27.35 (14)
C24—C23—C28—C27	−0.2 (3)	C6—C5—S1—O2	15.21 (14)
C21—C23—C28—C27	174.86 (17)	C4—C5—S1—O2	−161.53 (12)
C23—C28—C27—C26	−0.2 (3)	C6—C5—S1—N1	−96.37 (13)
C28—C27—C26—C25	0.7 (4)	C4—C5—S1—N1	86.89 (13)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg4 are the centroids of the C2–C7 and C15–C20 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.93	2.59	2.934 (2)	102
C8—H8···O3ⁱ	0.98	2.44	3.3659 (17)	158
C14—H14···O3ⁱ	0.93	2.57	3.3855 (19)	146
C24—H24···O2ⁱⁱ	0.93	2.59	3.289 (2)	132
C1—H1C···Cg4ⁱⁱⁱ	0.96	2.90	3.484 (2)	120
C11—H11···Cg2ⁱⁱⁱ	0.93	2.88	3.619 (17)	138

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₃ClN₂O₃S
M_r	503.00
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.8458 (3), 13.0191 (4), 17.6720 (5)
β (°)	103.757 (2)
V (Å³)	2423.75 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.25 × 0.22 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	32315, 7313, 5098
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.712

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.115, 1.05
No. of reflections	7313
No. of parameters	317
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.35

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg4 are the centroids of the C2–C7 and C15–C20 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.93	2.59	2.934 (2)	102
C8—H8···O3ⁱ	0.98	2.44	3.3659 (17)	158
C14—H14···O3ⁱ	0.93	2.57	3.3855 (19)	146
C24—H24···O2ⁱⁱ	0.93	2.59	3.289 (2)	132
C1—H1C···Cg4ⁱⁱⁱ	0.96	2.90	3.484 (2)	120
C11—H11···Cg2ⁱⁱⁱ	0.93	2.88	3.619 (17)	138

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z.

Acknowledgements

SR and ASP thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison Wisconsin, USA. Google Scholar
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chohan, Z. H. & Shad, H. A. (2007). J. Enz. Inhib. Med. Chem. 23, 369–379. Web of Science CrossRef Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Nieto, M. J., Alovero, F. L., Manzo, R. H. & Mazzieri, M. R. (2005). Eur. J. Med. Chem. 40, 361–369. Web of Science CrossRef PubMed CAS Google Scholar
Pomarnacka, E. & Kozlarska-Kedra, I. (2003). Farmaco, 58, 423–429. CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, W., Liang, T. C., Zheng, M. & Gao, X. (1995). Tetrahedron Lett. 36, 1181–1184. CrossRef CAS Web of Science Google Scholar
Zareef, M., Iqbal, R., De Dominguez, N. G., Rodrigues, J., Zaidi, J. H., Arfan, M. & Supuran, C. T. (2007). J. Enz. Inhib. Med. Chem. 22, 301–308. Web of Science CrossRef CAS Google Scholar

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