3-(4-Methoxy-phen-yl)-6-(phenyl-sulfon-yl)perhydro-1,3-thiazolo[3',4':1,2]pyrrolo[4,5-c]pyrrole.

In the title compound, C(21)H(24)N(2)O(3)S(2), the three five-membered rings adopt envelope conformations. The dihedral angle between the two aromatic rings is 68.4 (1)°. C-H⋯O inter-actions link the mol-ecules into a chain and the chains are cross-linked via C-H⋯π inter-actions involving the meth-oxy-phenyl 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 = 416.54

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.137

S = 1.00

4769 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.16 e Å−3

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 ▶).

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

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

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

C21H24N2O3S2	F000 = 880
Mr = 416.54	Dx = 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 = 2.4–28.0º
b = 8.3319 (5) Å	µ = 0.29 mm−1
c = 16.8828 (9) Å	T = 293 (2) K
β = 98.923 (1)º	Block, pale yellow
V = 2022.4 (2) Å3	0.24 × 0.23 × 0.21 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	3991 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Monochromator: graphite	θmax = 28.0º
T = 293(2) K	θmin = 2.4º
ω scans	h = −18→18
Absorption correction: none	k = −10→11
22482 measured reflections	l = −21→22
4769 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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.082P)2 + 0.473P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
4769 reflections	Δρmax = 0.46 e Å−3
254 parameters	Δρmin = −0.16 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
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)

	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)

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)

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

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) ; (ii) .