3-(4-Methoxy­phen­yl)-6-(phenyl­sulfon­yl)perhydro-1,3-thiazolo[3′,4′:1,2]pyrrolo[4,5-c]pyrrole

Sundaramoorthy, S.; Gayathri, D.; Velmurugan, D.; Ravikumar, K.; Poornachandran, M.

doi:10.1107/S1600536808002134

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o515

doi:10.1107/S1600536808002134

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3-(4-Methoxyphenyl)-6-(phenylsulfonyl)perhydro-1,3-thiazolo[3′,4′:1,2]pyrrolo[4,5-c]pyrrole

S. Sundaramoorthy,^a D. Gayathri,^a D. Velmurugan,^a ^* K. Ravikumar ^b and M. Poornachandran ^c

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600025, India, ^bLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500007, India, and ^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600025, India
^*Correspondence e-mail: d_velu@yahoo.com

(Received 10 December 2007; accepted 21 January 2008; online 25 January 2008)

In the title compound, C₂₁H₂₄N₂O₃S₂, the three five-membered rings adopt envelope conformations. The dihedral angle between the two aromatic rings is 68.4 (1)°. C—H⋯O interactions link the molecules into a chain and the chains are cross-linked via C—H⋯π interactions involving the methoxyphenyl ring.

Related literature

For puckering parameters, see: Cremer & Pople (1975 ). For asymmetry parameters, see: Nardelli (1983 ). For general background, see: Amal Raj et al. (2003 ); Tsuru et al. (1988 ). For a related structure, see: Kavitha et al. (2006 ).

Experimental

Crystal data

C₂₁H₂₄N₂O₃S₂
M_r = 416.54
Monoclinic, P 2₁ /c
a = 14.5533 (8) Å
b = 8.3319 (5) Å
c = 16.8828 (9) Å
β = 98.923 (1)°
V = 2022.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 293 (2) K
0.24 × 0.23 × 0.21 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: none
22482 measured reflections
4769 independent reflections
3991 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.137
S = 1.00
4769 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O1ⁱ	0.93	2.56	3.437 (3)	158
C3—H3⋯Cg1ⁱⁱ	0.98	2.76	3.729 (2)	172
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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, 2003 ); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002134/ci2542sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808002134/ci2542Isup2.hkl

checkCIF report

Comment top

Substituted pyrrolidine compounds have gained much importance as they are the structural elements of many alkaloids. The pyrrolidine derivatives have been found to possess antifungal activity against various pathogens (Amal Raj et al., 2003). Thiazolidine derivatives may act as potent inhibitors specific for Pro1yl Endopeptidase (Tsuru et al., 1988). In view of the above facts, we have undertaken the X-ray crystal structure determination of the title compound.

Bond lenghts and angles in the title molecule (Fig. 1) are comparable to those observed in a related structure (Kavitha et al., 2006). The sums of the bond angles around N1 (343.7°) and N2 (333.1°) indicate sp³-hybridization. The thiazolidine and the two pyrrolidine rings (N1/C1—C4, A, and C2/C3/N2/C5/C6, B) adopt envelope conformations. Atom N1 in ring A lies 0.597 (2) Å below the C1—C4 mean plane and atom C6 in ring B lies 0.563 (3) Å above the N2/C3/C2/C5 plane. In the thiazolidine ring, atom C6 deviates by 0.554 (3) Å from the plane of the rest of the atoms in the ring. The puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) are q₂ = 0.406 (2) Å, ϕ = 187.3 (3)° and Δ_s(N₁) = 6.5 (2)° for ring A, q₂ = 0.372 (2) Å, ϕ = 137.0 (3)° and Δ_s(C₆) = 4.2 (2)° for ring B, and q₂ = 0.378 (2) Å, ϕ = 69.8 (3)° and Δ_s(C₆) = 3.7 (2)° for the thiazolidine ring. The dihedral angle between the two aromatic rings is 68.4 (1)°.

The crystal packing is stabilized by C—H···O and C—H···π intermolecular interactions.

Related literature top

For puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Nardelli (1983). For general background, see: Amal Raj et al. (2003); Tsuru et al. (1988). For a related structure, see: Kavitha et al. (2006).

Experimental top

A mixture of 2-(N-allyl-N-phenylsulfonyl) butanal (1.0 mmol) and of 2-p-methoxyphenylthiazolidine-4-carboxylic acid (1.5 mmol) in dry toluene (30 ml) was refluxed under Dean-Stark conditions till the completion of the reaction (3 h). The reaction mixture was then concentrated under reduced pressure. The residue was extracted with dichloromethane (2× 20 ml) and water (2× 20 ml). The organic layer was washed with brine solution (2× 20 ml), dried over anhydrous sodium sulfate and concentrated in vacuum. The residue was then subjected to column chromatography (silica gel, 100–200 mesh) with hexane-ethylacetate (8:2) to obtain the cycloadduct. Single crystals were obtained by recrystallization from methanol.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound viewed down the b axis.

3-(4-Methoxyphenyl)-6-(phenylsulfonyl)perhydro-1,3- thiazolo[3',4':1,2]pyrrolo[4,5-c]pyrrole top

Crystal data top

C₂₁H₂₄N₂O₃S₂	F(000) = 880
M_r = 416.54	D_x = 1.368 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2394 reflections
a = 14.5533 (8) Å	θ = 2.4–28.0°
b = 8.3319 (5) Å	µ = 0.29 mm⁻¹
c = 16.8828 (9) Å	T = 293 K
β = 98.923 (1)°	Block, pale yellow
V = 2022.4 (2) Å³	0.24 × 0.23 × 0.21 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3991 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 28.0°, θ_min = 2.4°
ω scans	h = −18→18
22482 measured reflections	k = −10→11
4769 independent reflections	l = −21→22

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.082P)² + 0.473P] where P = (F_o² + 2F_c²)/3
4769 reflections	(Δ/σ)_max = 0.001
254 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₁H₂₄N₂O₃S₂	V = 2022.4 (2) Å³
M_r = 416.54	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.5533 (8) Å	µ = 0.29 mm⁻¹
b = 8.3319 (5) Å	T = 293 K
c = 16.8828 (9) Å	0.24 × 0.23 × 0.21 mm
β = 98.923 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3991 reflections with I > 2σ(I)
22482 measured reflections	R_int = 0.020
4769 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.00	Δρ_max = 0.46 e Å⁻³
4769 reflections	Δρ_min = −0.16 e Å⁻³
254 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	0.65354 (11)	0.0421 (2)	0.27798 (12)	0.0543 (4)
H1A	0.6206	0.0086	0.2262	0.065*
H1B	0.6116	0.0371	0.3173	0.065*
C2	0.74011 (12)	−0.0593 (2)	0.30329 (11)	0.0518 (4)
H2	0.7317	−0.1681	0.2813	0.062*
C3	0.81895 (10)	0.0293 (2)	0.26945 (9)	0.0439 (3)
H3	0.8425	−0.0356	0.2285	0.053*
C4	0.77552 (11)	0.1850 (2)	0.23356 (11)	0.0526 (4)
H4A	0.8180	0.2747	0.2453	0.063*
H4B	0.7576	0.1760	0.1760	0.063*
C5	0.77266 (13)	−0.0635 (3)	0.39390 (11)	0.0626 (5)
H5A	0.7481	0.0270	0.4201	0.075*
H5B	0.7534	−0.1622	0.4171	0.075*
C6	0.87749 (12)	−0.0543 (3)	0.40161 (10)	0.0569 (4)
H6	0.9046	−0.0132	0.4545	0.068*
C7	0.92284 (15)	−0.2141 (3)	0.38422 (15)	0.0727 (6)
H7A	0.8825	−0.2742	0.3436	0.087*
H7B	0.9354	−0.2788	0.4325	0.087*
C8	0.98632 (10)	0.04673 (19)	0.32061 (9)	0.0436 (3)
H8	0.9840	0.0590	0.2626	0.052*
C9	1.05361 (11)	0.16890 (19)	0.36222 (9)	0.0436 (3)
C10	1.14935 (12)	0.1485 (2)	0.36544 (12)	0.0550 (4)
H10	1.1713	0.0577	0.3423	0.066*
C11	1.21182 (12)	0.2592 (2)	0.40186 (11)	0.0564 (4)
H11	1.2752	0.2426	0.4032	0.068*
C12	1.18109 (11)	0.3950 (2)	0.43660 (9)	0.0479 (4)
C13	1.08652 (11)	0.4217 (2)	0.43145 (10)	0.0494 (4)
H13	1.0649	0.5149	0.4526	0.059*
C14	1.02415 (11)	0.3086 (2)	0.39456 (10)	0.0478 (4)
H14	0.9607	0.3274	0.3915	0.057*
C15	1.22176 (17)	0.6174 (3)	0.52376 (16)	0.0805 (6)
H15A	1.1852	0.6967	0.4918	0.121*
H15B	1.2763	0.6669	0.5529	0.121*
H15C	1.1857	0.5707	0.5608	0.121*
C16	0.56879 (11)	0.3179 (2)	0.15034 (11)	0.0500 (4)
C17	0.48978 (12)	0.2243 (2)	0.13751 (13)	0.0618 (5)
H17	0.4622	0.1885	0.1804	0.074*
C18	0.45196 (16)	0.1844 (3)	0.05922 (17)	0.0806 (7)
H18	0.3991	0.1203	0.0497	0.097*
C19	0.4920 (2)	0.2388 (4)	−0.00370 (16)	0.0903 (8)
H19	0.4664	0.2110	−0.0558	0.108*
C20	0.56928 (18)	0.3335 (4)	0.00945 (16)	0.0913 (8)
H20	0.5956	0.3713	−0.0337	0.110*
C21	0.60859 (14)	0.3736 (3)	0.08689 (14)	0.0717 (6)
H21	0.6615	0.4377	0.0959	0.086*
N1	0.69349 (9)	0.20342 (17)	0.27399 (8)	0.0463 (3)
N2	0.89254 (8)	0.05860 (16)	0.33850 (7)	0.0425 (3)
O1	1.24842 (9)	0.49627 (18)	0.47326 (9)	0.0655 (4)
O2	0.55465 (11)	0.3473 (2)	0.30071 (10)	0.0803 (5)
O3	0.68031 (11)	0.49379 (17)	0.24897 (11)	0.0845 (5)
S1	1.02851 (3)	−0.16174 (6)	0.34950 (3)	0.06126 (16)
S2	0.62353 (3)	0.35418 (5)	0.24924 (3)	0.05671 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0391 (8)	0.0524 (9)	0.0690 (11)	−0.0053 (7)	0.0012 (7)	0.0057 (8)
C2	0.0474 (9)	0.0442 (8)	0.0619 (10)	−0.0017 (7)	0.0025 (7)	0.0016 (7)
C3	0.0408 (7)	0.0513 (9)	0.0379 (7)	0.0052 (6)	0.0013 (6)	−0.0012 (6)
C4	0.0375 (8)	0.0647 (11)	0.0543 (9)	0.0039 (7)	0.0033 (7)	0.0166 (8)
C5	0.0539 (10)	0.0767 (13)	0.0591 (10)	0.0051 (9)	0.0148 (8)	0.0172 (9)
C6	0.0501 (9)	0.0787 (13)	0.0418 (8)	0.0110 (9)	0.0065 (7)	0.0119 (8)
C7	0.0654 (12)	0.0688 (13)	0.0853 (14)	0.0174 (10)	0.0158 (10)	0.0367 (11)
C8	0.0414 (7)	0.0472 (8)	0.0412 (7)	0.0091 (6)	0.0033 (6)	0.0006 (6)
C9	0.0405 (8)	0.0486 (8)	0.0402 (7)	0.0083 (6)	0.0018 (6)	0.0033 (6)
C10	0.0434 (8)	0.0551 (10)	0.0650 (10)	0.0143 (7)	0.0035 (7)	−0.0071 (8)
C11	0.0369 (8)	0.0617 (11)	0.0681 (11)	0.0100 (7)	0.0006 (7)	−0.0002 (9)
C12	0.0454 (8)	0.0520 (9)	0.0441 (8)	0.0009 (7)	0.0005 (6)	0.0052 (7)
C13	0.0495 (9)	0.0479 (9)	0.0507 (9)	0.0068 (7)	0.0080 (7)	−0.0013 (7)
C14	0.0380 (7)	0.0537 (9)	0.0513 (9)	0.0088 (7)	0.0052 (6)	−0.0007 (7)
C15	0.0727 (13)	0.0751 (14)	0.0901 (16)	−0.0104 (12)	0.0017 (12)	−0.0244 (12)
C16	0.0384 (8)	0.0460 (8)	0.0629 (10)	0.0071 (6)	−0.0007 (7)	0.0056 (7)
C17	0.0448 (9)	0.0581 (11)	0.0795 (13)	−0.0016 (8)	−0.0002 (8)	0.0085 (9)
C18	0.0584 (12)	0.0700 (13)	0.1027 (18)	−0.0003 (10)	−0.0211 (12)	−0.0081 (13)
C19	0.0831 (17)	0.108 (2)	0.0723 (14)	0.0324 (15)	−0.0127 (12)	−0.0067 (14)
C20	0.0679 (14)	0.135 (2)	0.0702 (14)	0.0243 (15)	0.0080 (11)	0.0286 (14)
C21	0.0458 (9)	0.0839 (14)	0.0830 (14)	0.0029 (9)	0.0022 (9)	0.0269 (12)
N1	0.0369 (6)	0.0462 (7)	0.0539 (7)	0.0004 (5)	0.0009 (5)	−0.0001 (6)
N2	0.0384 (6)	0.0499 (7)	0.0376 (6)	0.0061 (5)	0.0012 (5)	−0.0003 (5)
O1	0.0506 (7)	0.0672 (8)	0.0754 (9)	−0.0045 (6)	−0.0007 (6)	−0.0105 (7)
O2	0.0724 (9)	0.0955 (12)	0.0742 (9)	0.0299 (8)	0.0151 (7)	−0.0118 (8)
O3	0.0785 (10)	0.0448 (7)	0.1191 (13)	−0.0049 (7)	−0.0199 (9)	−0.0081 (8)
S1	0.0558 (3)	0.0487 (3)	0.0802 (3)	0.01351 (19)	0.0134 (2)	−0.0004 (2)
S2	0.0506 (3)	0.0477 (3)	0.0683 (3)	0.00750 (18)	−0.0018 (2)	−0.00786 (19)

Geometric parameters (Å, º) top

C1—N1	1.470 (2)	C10—C11	1.372 (3)
C1—C2	1.522 (2)	C10—H10	0.93
C1—H1A	0.97	C11—C12	1.381 (3)
C1—H1B	0.97	C11—H11	0.93
C2—C5	1.530 (3)	C12—O1	1.367 (2)
C2—C3	1.546 (2)	C12—C13	1.384 (2)
C2—H2	0.98	C13—C14	1.387 (2)
C3—N2	1.4760 (18)	C13—H13	0.93
C3—C4	1.527 (2)	C14—H14	0.93
C3—H3	0.98	C15—O1	1.413 (3)
C4—N1	1.472 (2)	C15—H15A	0.96
C4—H4A	0.97	C15—H15B	0.96
C4—H4B	0.97	C15—H15C	0.96
C5—C6	1.513 (2)	C16—C21	1.375 (3)
C5—H5A	0.97	C16—C17	1.378 (2)
C5—H5B	0.97	C16—S2	1.7611 (18)
C6—N2	1.463 (2)	C17—C18	1.391 (3)
C6—C7	1.534 (3)	C17—H17	0.93
C6—H6	0.98	C18—C19	1.366 (4)
C7—S1	1.783 (2)	C18—H18	0.93
C7—H7A	0.97	C19—C20	1.364 (4)
C7—H7B	0.97	C19—H19	0.93
C8—N2	1.4461 (19)	C20—C21	1.384 (4)
C8—C9	1.508 (2)	C20—H20	0.93
C8—S1	1.8812 (16)	C21—H21	0.93
C8—H8	0.98	N1—S2	1.630 (1)
C9—C14	1.382 (2)	O2—S2	1.426 (2)
C9—C10	1.396 (2)	O3—S2	1.427 (2)

N1—C1—C2	101.78 (13)	C11—C10—H10	119.2
N1—C1—H1A	111.4	C9—C10—H10	119.2
C2—C1—H1A	111.4	C10—C11—C12	120.36 (15)
N1—C1—H1B	111.4	C10—C11—H11	119.8
C2—C1—H1B	111.4	C12—C11—H11	119.8
H1A—C1—H1B	109.3	O1—C12—C11	116.22 (15)
C1—C2—C5	114.08 (16)	O1—C12—C13	124.43 (16)
C1—C2—C3	105.12 (13)	C11—C12—C13	119.34 (16)
C5—C2—C3	104.36 (13)	C12—C13—C14	119.61 (16)
C1—C2—H2	111.0	C12—C13—H13	120.2
C5—C2—H2	111.0	C14—C13—H13	120.2
C3—C2—H2	111.0	C9—C14—C13	121.87 (15)
N2—C3—C4	112.20 (14)	C9—C14—H14	119.1
N2—C3—C2	106.04 (12)	C13—C14—H14	119.1
C4—C3—C2	105.49 (12)	O1—C15—H15A	109.5
N2—C3—H3	111.0	O1—C15—H15B	109.5
C4—C3—H3	111.0	H15A—C15—H15B	109.5
C2—C3—H3	111.0	O1—C15—H15C	109.5
N1—C4—C3	102.71 (13)	H15A—C15—H15C	109.5
N1—C4—H4A	111.2	H15B—C15—H15C	109.5
C3—C4—H4A	111.2	C21—C16—C17	120.69 (19)
N1—C4—H4B	111.2	C21—C16—S2	119.82 (15)
C3—C4—H4B	111.2	C17—C16—S2	119.33 (15)
H4A—C4—H4B	109.1	C16—C17—C18	118.8 (2)
C6—C5—C2	103.68 (14)	C16—C17—H17	120.6
C6—C5—H5A	111.0	C18—C17—H17	120.6
C2—C5—H5A	111.0	C19—C18—C17	120.4 (2)
C6—C5—H5B	111.0	C19—C18—H18	119.8
C2—C5—H5B	111.0	C17—C18—H18	119.8
H5A—C5—H5B	109.0	C18—C19—C20	120.4 (2)
N2—C6—C5	103.46 (13)	C18—C19—H19	119.8
N2—C6—C7	107.54 (14)	C20—C19—H19	119.8
C5—C6—C7	113.43 (19)	C19—C20—C21	120.2 (2)
N2—C6—H6	110.7	C19—C20—H20	119.9
C5—C6—H6	110.7	C21—C20—H20	119.9
C7—C6—H6	110.7	C16—C21—C20	119.5 (2)
C6—C7—S1	105.61 (15)	C16—C21—H21	120.3
C6—C7—H7A	110.6	C20—C21—H21	120.3
S1—C7—H7A	110.6	C1—N1—C4	106.32 (14)
C6—C7—H7B	110.6	C1—N1—S2	118.72 (10)
S1—C7—H7B	110.6	C4—N1—S2	118.72 (11)
H7A—C7—H7B	108.8	C8—N2—C6	111.15 (12)
N2—C8—C9	114.97 (13)	C8—N2—C3	114.61 (12)
N2—C8—S1	106.84 (11)	C6—N2—C3	107.25 (13)
C9—C8—S1	109.88 (10)	C12—O1—C15	117.99 (15)
N2—C8—H8	108.3	C7—S1—C8	92.74 (8)
C9—C8—H8	108.3	O3—S2—O2	119.8 (1)
S1—C8—H8	108.3	O3—S2—N1	106.9 (1)
C14—C9—C10	117.13 (16)	O2—S2—N1	106.4 (1)
C14—C9—C8	122.25 (14)	O3—S2—C16	108.3 (1)
C10—C9—C8	120.52 (14)	O2—S2—C16	108.3 (1)
C11—C10—C9	121.58 (16)	N1—S2—C16	106.5 (1)

N1—C1—C2—C5	84.89 (18)	C19—C20—C21—C16	−0.4 (4)
N1—C1—C2—C3	−28.83 (17)	C2—C1—N1—C4	43.59 (17)
C1—C2—C3—N2	124.51 (14)	C2—C1—N1—S2	−179.41 (12)
C5—C2—C3—N2	4.15 (18)	C3—C4—N1—C1	−40.24 (16)
C1—C2—C3—C4	5.32 (18)	C3—C4—N1—S2	−177.24 (11)
C5—C2—C3—C4	−115.04 (15)	C9—C8—N2—C6	−96.95 (16)
N2—C3—C4—N1	−94.75 (15)	S1—C8—N2—C6	25.25 (15)
C2—C3—C4—N1	20.26 (17)	C9—C8—N2—C3	141.25 (14)
C1—C2—C5—C6	−140.00 (16)	S1—C8—N2—C3	−96.54 (13)
C3—C2—C5—C6	−25.83 (19)	C5—C6—N2—C8	−162.77 (15)
C2—C5—C6—N2	38.5 (2)	C7—C6—N2—C8	−42.48 (19)
C2—C5—C6—C7	−77.72 (19)	C5—C6—N2—C3	−36.79 (18)
N2—C6—C7—S1	39.16 (19)	C7—C6—N2—C3	83.51 (17)
C5—C6—C7—S1	152.93 (13)	C4—C3—N2—C8	−101.22 (15)
N2—C8—C9—C14	−18.7 (2)	C2—C3—N2—C8	144.10 (13)
S1—C8—C9—C14	−139.26 (14)	C4—C3—N2—C6	134.88 (14)
N2—C8—C9—C10	164.94 (15)	C2—C3—N2—C6	20.21 (17)
S1—C8—C9—C10	44.39 (19)	C11—C12—O1—C15	−166.82 (19)
C14—C9—C10—C11	2.5 (3)	C13—C12—O1—C15	14.2 (3)
C8—C9—C10—C11	178.99 (17)	C6—C7—S1—C8	−21.16 (15)
C9—C10—C11—C12	0.0 (3)	N2—C8—S1—C7	−1.24 (13)
C10—C11—C12—O1	178.36 (17)	C9—C8—S1—C7	124.11 (13)
C10—C11—C12—C13	−2.6 (3)	C1—N1—S2—O3	−179.18 (14)
O1—C12—C13—C14	−178.35 (16)	C4—N1—S2—O3	−47.46 (16)
C11—C12—C13—C14	2.7 (3)	C1—N1—S2—O2	51.72 (16)
C10—C9—C14—C13	−2.4 (3)	C4—N1—S2—O2	−176.55 (13)
C8—C9—C14—C13	−178.82 (15)	C1—N1—S2—C16	−63.61 (15)
C12—C13—C14—C9	−0.2 (3)	C4—N1—S2—C16	68.11 (14)
C21—C16—C17—C18	1.3 (3)	C21—C16—S2—O3	24.79 (18)
S2—C16—C17—C18	−174.25 (15)	C17—C16—S2—O3	−159.64 (15)
C16—C17—C18—C19	−0.7 (3)	C21—C16—S2—O2	156.12 (16)
C17—C18—C19—C20	−0.3 (4)	C17—C16—S2—O2	−28.32 (18)
C18—C19—C20—C21	0.9 (4)	C21—C16—S2—N1	−89.80 (17)
C17—C16—C21—C20	−0.7 (3)	C17—C16—S2—N1	85.77 (16)
S2—C16—C21—C20	174.78 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O1ⁱ	0.93	2.56	3.437 (3)	158
C3—H3···Cg1ⁱⁱ	0.98	2.76	3.729 (2)	172

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄N₂O₃S₂
M_r	416.54
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.5533 (8), 8.3319 (5), 16.8828 (9)
β (°)	98.923 (1)
V (Å³)	2022.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.24 × 0.23 × 0.21

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	22482, 4769, 3991
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.137, 1.00
No. of reflections	4769
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.16

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O1ⁱ	0.93	2.56	3.437 (3)	158
C3—H3···Cg1ⁱⁱ	0.98	2.76	3.729 (2)	172

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

Acknowledgements

DG thanks the Council of Scientific and Industrial Research (CSIR), India, for a Senior Research Fellowship. The University Grants Commission (UGC–SAP) and Department of Science and Technology (DST–FIST), Government of India, are acknowledged by DV for providing facilities to the department.

References

Amal Raj, A., Raghunathan, R., Sridevi Kumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407–409. Web of Science PubMed Google Scholar
Bruker (2001). SMART (Version 5.625/NT/2000) and SAINT (Version 6.28a). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Kavitha, V., Gayathri, D. R., Velmurugan, D., Ravikumar, K. & Poornachandran, M. (2006). Acta Cryst. E62, o2146–o2148. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tsuru, D., Yoshimoto, T., Koriyama, N. & Furukawa, S. (1988). J. Biochem. 104, 580–586. CAS PubMed Web of Science Google Scholar

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Volume 64| Part 2| February 2008| Page o515

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

3-(4-Meth­oxy­phen­yl)-6-(phenyl­sulfon­yl)perhydro-1,3-thiazolo[3′,4′:1,2]pyrrolo[4,5-c]pyrrole

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-(4-Methoxyphenyl)-6-(phenylsulfonyl)perhydro-1,3-thiazolo[3′,4′:1,2]pyrrolo[4,5-c]pyrrole