1'-Phenyl-6'-thia-cyclo-heptane-1-spiro-2'-perhydro-pyrrolizine-3'-spiro-3''-indoline-2,2''-dione.

The thia-zolidine ring and the pyrrolidine ring in the title compound, C(25)H(26)N(2)O(2)S, both adopt an envelope conformation. The seven-membered ring has a twist-chair conformation. The crystal packing is stabilized by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Amal Raj et al. (2003 ▶); Cremer & Pople (1975 ▶); Kumar et al. (2006 ▶); Nardelli (1983 ▶); Si et al. (2005 ▶).

Experimental

Crystal data

C25H26N2O2S

M = 418.54

Triclinic,

a = 8.9846 (10) Å

b = 10.3564 (11) Å

c = 12.8124 (14) Å

α = 80.147 (2)°

β = 71.012 (2)°

γ = 67.497 (2)°

V = 1040.0 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 293 (2) K

0.26 × 0.25 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

11582 measured reflections

4697 independent reflections

3880 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.157

S = 1.08

4697 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.20 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/S1600536807068705/bt2666sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068705/bt2666Isup2.hkl

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

C25H26N2O2S	Z = 2
Mr = 418.54	F000 = 444
Triclinic, P1	Dx = 1.337 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.9846 (10) Å	Cell parameters from 2358 reflections
b = 10.3564 (11) Å	θ = 1.7–25.0º
c = 12.8124 (14) Å	µ = 0.18 mm−1
α = 80.147 (2)º	T = 293 (2) K
β = 71.012 (2)º	Block, colorless
γ = 67.497 (2)º	0.26 × 0.25 × 0.23 mm
V = 1040.0 (2) Å3

Bruker SMART CCD area-detector diffractometer	3880 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Monochromator: graphite	θmax = 28.0º
T = 293(2) K	θmin = 1.7º
ω scans	h = −11→11
Absorption correction: none	k = −13→13
11582 measured reflections	l = −16→16
4697 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)] = 0.062	H-atom parameters constrained
wR(F2) = 0.157	w = 1/[σ2(Fo2) + (0.0833P)2 + 0.2981P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
4697 reflections	Δρmax = 0.36 e Å−3
271 parameters	Δρmin = −0.20 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	0.2327 (2)	0.71980 (19)	0.35784 (14)	0.0267 (4)
C2	0.1643 (2)	0.84561 (18)	0.27522 (14)	0.0245 (4)
C3	0.2629 (2)	0.93969 (19)	0.27834 (14)	0.0275 (4)
H3	0.3807	0.8916	0.2386	0.033*
C4	0.2543 (2)	0.9308 (2)	0.39991 (15)	0.0309 (4)
H4	0.1503	1.0022	0.4386	0.037*
C5	0.4043 (3)	0.9465 (3)	0.4219 (2)	0.0486 (6)
H5A	0.3675	0.9961	0.4887	0.058*
H5B	0.4568	0.9989	0.3607	0.058*
C6	0.3716 (3)	0.7143 (3)	0.4993 (2)	0.0477 (6)
H6A	0.4063	0.6146	0.4918	0.057*
H6B	0.3256	0.7325	0.5773	0.057*
C7	0.1116 (2)	0.63856 (19)	0.41978 (14)	0.0283 (4)
C8	0.3423 (3)	0.4830 (2)	0.31052 (16)	0.0340 (4)
C9	0.4440 (3)	0.3632 (2)	0.25409 (19)	0.0474 (6)
H9	0.4118	0.2855	0.2648	0.057*
C10	0.5958 (3)	0.3639 (3)	0.1810 (2)	0.0552 (7)
H10	0.6665	0.2857	0.1404	0.066*
C11	0.6440 (3)	0.4783 (3)	0.1674 (2)	0.0521 (6)
H11	0.7482	0.4750	0.1193	0.063*
C12	0.5404 (3)	0.5984 (2)	0.22390 (18)	0.0410 (5)
H12	0.5741	0.6752	0.2141	0.049*
C13	0.3852 (2)	0.6016 (2)	0.29553 (15)	0.0311 (4)
C14	0.2143 (3)	0.79473 (19)	0.15917 (15)	0.0312 (4)
C15	0.1212 (3)	0.7116 (2)	0.13959 (18)	0.0435 (5)
H15A	0.0694	0.6711	0.2093	0.052*
H15B	0.1990	0.6360	0.0920	0.052*
C16	−0.0142 (4)	0.8082 (3)	0.0852 (2)	0.0584 (7)
H16A	0.0370	0.8584	0.0216	0.070*
H16B	−0.0576	0.7514	0.0588	0.070*
C17	−0.1593 (3)	0.9132 (3)	0.1619 (2)	0.0600 (7)
H17A	−0.2234	0.8631	0.2172	0.072*
H17B	−0.2326	0.9763	0.1193	0.072*
C18	−0.1110 (3)	1.0007 (2)	0.22123 (19)	0.0433 (5)
H18A	−0.2113	1.0777	0.2538	0.052*
H18B	−0.0339	1.0406	0.1669	0.052*
C19	−0.0288 (2)	0.9197 (2)	0.31231 (15)	0.0307 (4)
H19A	−0.0793	0.8497	0.3474	0.037*
H19B	−0.0561	0.9844	0.3679	0.037*
C20	0.2132 (2)	1.0876 (2)	0.22729 (15)	0.0300 (4)
C21	0.3124 (3)	1.1172 (2)	0.12397 (17)	0.0393 (5)
H21	0.4070	1.0459	0.0876	0.047*
C22	0.2726 (3)	1.2504 (3)	0.07487 (19)	0.0503 (6)
H22	0.3406	1.2681	0.0060	0.060*
C23	0.1336 (4)	1.3570 (2)	0.1268 (2)	0.0512 (6)
H23	0.1051	1.4461	0.0924	0.061*
C24	0.0365 (3)	1.3313 (2)	0.2302 (2)	0.0477 (6)
H24	−0.0565	1.4039	0.2665	0.057*
C25	0.0765 (3)	1.1980 (2)	0.28063 (18)	0.0385 (5)
H25	0.0110	1.1822	0.3511	0.046*
N1	0.2471 (2)	0.79135 (17)	0.44146 (12)	0.0312 (4)
N2	0.1822 (2)	0.50686 (17)	0.38528 (14)	0.0365 (4)
H2	0.1347	0.4451	0.4066	0.044*
O1	−0.02147 (18)	0.68469 (15)	0.49036 (11)	0.0377 (3)
O2	0.3167 (2)	0.82744 (17)	0.08308 (11)	0.0449 (4)
S1	0.55069 (8)	0.77332 (8)	0.43717 (6)	0.0609 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0286 (9)	0.0307 (9)	0.0235 (8)	−0.0144 (8)	−0.0074 (7)	0.0014 (7)
C2	0.0295 (9)	0.0258 (9)	0.0194 (8)	−0.0125 (7)	−0.0066 (7)	0.0012 (7)
C3	0.0301 (9)	0.0301 (9)	0.0234 (9)	−0.0143 (8)	−0.0045 (7)	−0.0014 (7)
C4	0.0358 (10)	0.0354 (10)	0.0264 (9)	−0.0176 (8)	−0.0091 (8)	−0.0014 (8)
C5	0.0577 (15)	0.0605 (15)	0.0485 (13)	−0.0368 (12)	−0.0255 (11)	0.0027 (11)
C6	0.0591 (15)	0.0524 (14)	0.0437 (12)	−0.0251 (12)	−0.0296 (11)	0.0099 (10)
C7	0.0345 (10)	0.0316 (10)	0.0220 (8)	−0.0166 (8)	−0.0096 (7)	0.0051 (7)
C8	0.0395 (11)	0.0309 (10)	0.0289 (9)	−0.0104 (9)	−0.0115 (8)	0.0039 (8)
C9	0.0591 (15)	0.0308 (11)	0.0446 (12)	−0.0088 (10)	−0.0154 (11)	0.0015 (9)
C10	0.0559 (15)	0.0376 (12)	0.0446 (13)	0.0071 (11)	−0.0077 (11)	−0.0015 (10)
C11	0.0362 (12)	0.0530 (15)	0.0435 (13)	−0.0005 (11)	−0.0028 (10)	0.0044 (11)
C12	0.0337 (11)	0.0433 (12)	0.0383 (11)	−0.0108 (9)	−0.0075 (9)	0.0052 (9)
C13	0.0316 (10)	0.0327 (10)	0.0259 (9)	−0.0092 (8)	−0.0100 (8)	0.0043 (7)
C14	0.0404 (11)	0.0272 (9)	0.0255 (9)	−0.0110 (8)	−0.0103 (8)	0.0001 (7)
C15	0.0661 (15)	0.0409 (12)	0.0357 (11)	−0.0268 (11)	−0.0212 (10)	−0.0010 (9)
C16	0.0824 (19)	0.0688 (17)	0.0485 (14)	−0.0382 (15)	−0.0401 (14)	0.0050 (12)
C17	0.0601 (16)	0.0745 (18)	0.0625 (16)	−0.0296 (14)	−0.0409 (14)	0.0135 (14)
C18	0.0408 (12)	0.0444 (12)	0.0435 (12)	−0.0107 (10)	−0.0202 (10)	0.0068 (10)
C19	0.0298 (10)	0.0352 (10)	0.0259 (9)	−0.0123 (8)	−0.0075 (8)	0.0028 (8)
C20	0.0372 (10)	0.0313 (10)	0.0273 (9)	−0.0189 (8)	−0.0090 (8)	0.0001 (7)
C21	0.0471 (12)	0.0397 (11)	0.0316 (10)	−0.0215 (10)	−0.0057 (9)	0.0000 (9)
C22	0.0710 (17)	0.0501 (14)	0.0367 (12)	−0.0360 (13)	−0.0131 (11)	0.0110 (10)
C23	0.0764 (17)	0.0352 (12)	0.0554 (14)	−0.0290 (12)	−0.0331 (13)	0.0147 (10)
C24	0.0562 (14)	0.0318 (11)	0.0581 (14)	−0.0125 (10)	−0.0222 (12)	−0.0057 (10)
C25	0.0442 (12)	0.0363 (11)	0.0350 (10)	−0.0169 (9)	−0.0070 (9)	−0.0037 (9)
N1	0.0371 (9)	0.0375 (9)	0.0259 (8)	−0.0184 (7)	−0.0141 (7)	0.0032 (7)
N2	0.0430 (10)	0.0299 (8)	0.0372 (9)	−0.0191 (7)	−0.0074 (8)	0.0041 (7)
O1	0.0382 (8)	0.0393 (8)	0.0332 (7)	−0.0206 (6)	−0.0002 (6)	0.0013 (6)
O2	0.0558 (10)	0.0530 (9)	0.0247 (7)	−0.0257 (8)	0.0002 (7)	−0.0059 (6)
S1	0.0454 (4)	0.0753 (5)	0.0743 (5)	−0.0243 (3)	−0.0318 (3)	0.0007 (4)

C1—N1	1.466 (2)	C12—C13	1.389 (3)
C1—C13	1.534 (3)	C12—H12	0.9300
C1—C7	1.560 (2)	C14—O2	1.206 (2)
C1—C2	1.592 (2)	C14—C15	1.505 (3)
C2—C14	1.531 (2)	C15—C16	1.532 (3)
C2—C19	1.547 (3)	C15—H15A	0.9700
C2—C3	1.560 (2)	C15—H15B	0.9700
C3—C20	1.516 (3)	C16—C17	1.514 (4)
C3—C4	1.523 (2)	C16—H16A	0.9700
C3—H3	0.9800	C16—H16B	0.9700
C4—N1	1.469 (2)	C17—C18	1.530 (3)
C4—C5	1.535 (3)	C17—H17A	0.9700
C4—H4	0.9800	C17—H17B	0.9700
C5—S1	1.796 (3)	C18—C19	1.537 (3)
C5—H5A	0.9700	C18—H18A	0.9700
C5—H5B	0.9700	C18—H18B	0.9700
C6—N1	1.445 (3)	C19—H19A	0.9700
C6—S1	1.830 (2)	C19—H19B	0.9700
C6—H6A	0.9700	C20—C25	1.389 (3)
C6—H6B	0.9700	C20—C21	1.394 (3)
C7—O1	1.217 (2)	C21—C22	1.378 (3)
C7—N2	1.349 (2)	C21—H21	0.9300
C8—C9	1.381 (3)	C22—C23	1.370 (4)
C8—C13	1.388 (3)	C22—H22	0.9300
C8—N2	1.400 (3)	C23—C24	1.375 (4)
C9—C10	1.382 (3)	C23—H23	0.9300
C9—H9	0.9300	C24—C25	1.385 (3)
C10—C11	1.377 (4)	C24—H24	0.9300
C10—H10	0.9300	C25—H25	0.9300
C11—C12	1.386 (3)	N2—H2	0.8600
C11—H11	0.9300
N1—C1—C13	120.41 (15)	O2—C14—C2	121.75 (17)
N1—C1—C7	106.89 (14)	C15—C14—C2	118.00 (17)
C13—C1—C7	100.64 (14)	C14—C15—C16	109.25 (18)
N1—C1—C2	102.68 (14)	C14—C15—H15A	109.8
C13—C1—C2	111.37 (14)	C16—C15—H15A	109.8
C7—C1—C2	115.44 (14)	C14—C15—H15B	109.8
C14—C2—C19	108.15 (15)	C16—C15—H15B	109.8
C14—C2—C3	111.12 (14)	H15A—C15—H15B	108.3
C19—C2—C3	113.41 (15)	C17—C16—C15	113.6 (2)
C14—C2—C1	110.81 (14)	C17—C16—H16A	108.8
C19—C2—C1	113.62 (14)	C15—C16—H16A	108.8
C3—C2—C1	99.60 (13)	C17—C16—H16B	108.8
C20—C3—C4	114.20 (15)	C15—C16—H16B	108.8
C20—C3—C2	118.60 (15)	H16A—C16—H16B	107.7
C4—C3—C2	103.40 (14)	C16—C17—C18	115.7 (2)
C20—C3—H3	106.6	C16—C17—H17A	108.4
C4—C3—H3	106.6	C18—C17—H17A	108.4
C2—C3—H3	106.6	C16—C17—H17B	108.4
N1—C4—C3	104.86 (14)	C18—C17—H17B	108.4
N1—C4—C5	109.38 (17)	H17A—C17—H17B	107.4
C3—C4—C5	114.85 (16)	C17—C18—C19	114.69 (19)
N1—C4—H4	109.2	C17—C18—H18A	108.6
C3—C4—H4	109.2	C19—C18—H18A	108.6
C5—C4—H4	109.2	C17—C18—H18B	108.6
C4—C5—S1	107.24 (15)	C19—C18—H18B	108.6
C4—C5—H5A	110.3	H18A—C18—H18B	107.6
S1—C5—H5A	110.3	C18—C19—C2	116.35 (16)
C4—C5—H5B	110.3	C18—C19—H19A	108.2
S1—C5—H5B	110.3	C2—C19—H19A	108.2
H5A—C5—H5B	108.5	C18—C19—H19B	108.2
N1—C6—S1	107.08 (15)	C2—C19—H19B	108.2
N1—C6—H6A	110.3	H19A—C19—H19B	107.4
S1—C6—H6A	110.3	C25—C20—C21	117.67 (18)
N1—C6—H6B	110.3	C25—C20—C3	123.12 (17)
S1—C6—H6B	110.3	C21—C20—C3	119.15 (18)
H6A—C6—H6B	108.6	C22—C21—C20	121.1 (2)
O1—C7—N2	125.70 (17)	C22—C21—H21	119.5
O1—C7—C1	125.71 (17)	C20—C21—H21	119.5
N2—C7—C1	108.54 (16)	C23—C22—C21	120.4 (2)
C9—C8—C13	123.1 (2)	C23—C22—H22	119.8
C9—C8—N2	126.65 (19)	C21—C22—H22	119.8
C13—C8—N2	110.23 (17)	C22—C23—C24	119.5 (2)
C8—C9—C10	117.0 (2)	C22—C23—H23	120.2
C8—C9—H9	121.5	C24—C23—H23	120.2
C10—C9—H9	121.5	C23—C24—C25	120.4 (2)
C11—C10—C9	121.1 (2)	C23—C24—H24	119.8
C11—C10—H10	119.5	C25—C24—H24	119.8
C9—C10—H10	119.5	C24—C25—C20	120.8 (2)
C10—C11—C12	121.4 (2)	C24—C25—H25	119.6
C10—C11—H11	119.3	C20—C25—H25	119.6
C12—C11—H11	119.3	C6—N1—C1	117.96 (17)
C11—C12—C13	118.6 (2)	C6—N1—C4	112.11 (16)
C11—C12—H12	120.7	C1—N1—C4	111.66 (14)
C13—C12—H12	120.7	C7—N2—C8	111.73 (16)
C8—C13—C12	118.80 (19)	C7—N2—H2	124.1
C8—C13—C1	108.37 (16)	C8—N2—H2	124.1
C12—C13—C1	132.51 (18)	C5—S1—C6	88.36 (11)
O2—C14—C15	120.06 (18)
N1—C1—C2—C14	154.06 (15)	C3—C2—C14—O2	−0.4 (3)
C13—C1—C2—C14	23.9 (2)	C1—C2—C14—O2	−110.2 (2)
C7—C1—C2—C14	−90.04 (18)	C19—C2—C14—C15	−50.3 (2)
N1—C1—C2—C19	−83.94 (17)	C3—C2—C14—C15	−175.42 (17)
C13—C1—C2—C19	145.89 (16)	C1—C2—C14—C15	74.8 (2)
C7—C1—C2—C19	32.0 (2)	O2—C14—C15—C16	−75.9 (3)
N1—C1—C2—C3	36.98 (16)	C2—C14—C15—C16	99.2 (2)
C13—C1—C2—C3	−93.19 (16)	C14—C15—C16—C17	−70.3 (3)
C7—C1—C2—C3	152.88 (15)	C15—C16—C17—C18	52.0 (3)
C14—C2—C3—C20	74.5 (2)	C16—C17—C18—C19	−71.4 (3)
C19—C2—C3—C20	−47.6 (2)	C17—C18—C19—C2	87.6 (2)
C1—C2—C3—C20	−168.64 (15)	C14—C2—C19—C18	−34.2 (2)
C14—C2—C3—C4	−157.92 (15)	C3—C2—C19—C18	89.6 (2)
C19—C2—C3—C4	80.01 (17)	C1—C2—C19—C18	−157.62 (16)
C1—C2—C3—C4	−41.06 (17)	C4—C3—C20—C25	−42.5 (3)
C20—C3—C4—N1	160.57 (15)	C2—C3—C20—C25	79.8 (2)
C2—C3—C4—N1	30.29 (18)	C4—C3—C20—C21	134.67 (19)
C20—C3—C4—C5	−79.4 (2)	C2—C3—C20—C21	−103.0 (2)
C2—C3—C4—C5	150.37 (17)	C25—C20—C21—C22	−2.2 (3)
N1—C4—C5—S1	22.4 (2)	C3—C20—C21—C22	−179.53 (19)
C3—C4—C5—S1	−95.20 (18)	C20—C21—C22—C23	−0.2 (4)
N1—C1—C7—O1	45.1 (2)	C21—C22—C23—C24	2.1 (4)
C13—C1—C7—O1	171.63 (18)	C22—C23—C24—C25	−1.5 (4)
C2—C1—C7—O1	−68.4 (2)	C23—C24—C25—C20	−1.0 (3)
N1—C1—C7—N2	−132.43 (16)	C21—C20—C25—C24	2.8 (3)
C13—C1—C7—N2	−5.90 (18)	C3—C20—C25—C24	−179.97 (19)
C2—C1—C7—N2	114.09 (17)	S1—C6—N1—C1	101.84 (17)
C13—C8—C9—C10	0.9 (3)	S1—C6—N1—C4	−30.0 (2)
N2—C8—C9—C10	177.8 (2)	C13—C1—N1—C6	−27.7 (2)
C8—C9—C10—C11	1.4 (4)	C7—C1—N1—C6	86.0 (2)
C9—C10—C11—C12	−1.9 (4)	C2—C1—N1—C6	−152.11 (16)
C10—C11—C12—C13	0.1 (4)	C13—C1—N1—C4	104.30 (18)
C9—C8—C13—C12	−2.7 (3)	C7—C1—N1—C4	−142.00 (16)
N2—C8—C13—C12	179.99 (17)	C2—C1—N1—C4	−20.10 (19)
C9—C8—C13—C1	171.59 (19)	C3—C4—N1—C6	128.85 (18)
N2—C8—C13—C1	−5.7 (2)	C5—C4—N1—C6	5.2 (2)
C11—C12—C13—C8	2.1 (3)	C3—C4—N1—C1	−6.0 (2)
C11—C12—C13—C1	−170.5 (2)	C5—C4—N1—C1	−129.71 (17)
N1—C1—C13—C8	123.82 (18)	O1—C7—N2—C8	−174.57 (18)
C7—C1—C13—C8	6.88 (19)	C1—C7—N2—C8	3.0 (2)
C2—C1—C13—C8	−116.00 (16)	C9—C8—N2—C7	−175.5 (2)
N1—C1—C13—C12	−63.0 (3)	C13—C8—N2—C7	1.8 (2)
C7—C1—C13—C12	−179.9 (2)	C4—C5—S1—C6	−33.23 (16)
C2—C1—C13—C12	57.2 (3)	N1—C6—S1—C5	36.70 (17)
C19—C2—C14—O2	124.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.86	2.04	2.859 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.86	2.04	2.859 (2)	160

Symmetry code: (i) .