N-(1-Acetyl-r-7,c-9-diphenyl-4,8-dithia-1,2-diaza-spiro-[5.4]dec-2-en-3-yl)acet-amide.

In the title compound, C(22)H(23)N(3)O(2)S(2), the five-membered ring is planar and the C(5)S ring adopts a chair conformation. The crystal packing is stabilized by inter-molecular N-H⋯O and C-H⋯O inter-actions, generating a chain and a centrosymmetric dimer, respectively.

Related literature

For related literature, see: Allen et al. (1987 ▶); Isaac et al. (2003 ▶); Pan et al. (2003 ▶); Jung et al. (2004 ▶); Foroumadi et al. (2002 ▶); Jalilian et al. (2002 ▶); Leung-Toung et al. (2003 ▶); Schmidt et al. (1970 ▶); Cremer & Pople (1975 ▶); Nardelli (1983 ▶); Singh et al. (2003 ▶).

Experimental

Crystal data

C22H23N3O2S2

M = 425.55

Monoclinic,

a = 12.3310 (7) Å

b = 16.0218 (9) Å

c = 12.3852 (7) Å

β = 116.714 (1)°

V = 2185.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 (2) K

0.25 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: none

24434 measured reflections

5139 independent reflections

4587 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.116

S = 0.97

5139 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.17 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/S1600536808001025/at2527sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001025/at2527Isup2.hkl

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

C22H23N3O2S2	F000 = 896
Mr = 425.55	Dx = 1.293 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2504 reflections
a = 12.3310 (7) Å	θ = 1.9–28.0º
b = 16.0218 (9) Å	µ = 0.27 mm−1
c = 12.3852 (7) Å	T = 293 (2) K
β = 116.714 (1)º	Block, colourless
V = 2185.7 (2) Å3	0.25 × 0.24 × 0.22 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	4587 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Monochromator: graphite	θmax = 28.0º
T = 293(2) K	θmin = 1.9º
ω scans	h = −15→15
Absorption correction: none	k = −21→21
24434 measured reflections	l = −16→16
5139 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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0759P)2 + 0.4937P] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max = 0.031
5139 reflections	Δρmax = 0.31 e Å−3
264 parameters	Δρmin = −0.17 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	0.81098 (11)	0.05407 (8)	0.11215 (12)	0.0408 (3)
H1	0.8386	0.0188	0.1844	0.049*
C2	0.91557 (11)	0.11046 (8)	0.12512 (12)	0.0409 (3)
H2A	0.8872	0.1490	0.0575	0.049*
H2B	0.9794	0.0766	0.1221	0.049*
C3	0.96801 (10)	0.16028 (8)	0.24349 (11)	0.0377 (3)
C4	0.87477 (11)	0.21761 (8)	0.25620 (12)	0.0405 (3)
H4A	0.9135	0.2456	0.3338	0.049*
H4B	0.8499	0.2601	0.1938	0.049*
C5	0.76159 (11)	0.17236 (8)	0.24675 (12)	0.0403 (3)
H5	0.7863	0.1315	0.3124	0.048*
C6	0.67241 (12)	0.23270 (8)	0.25743 (12)	0.0418 (3)
C7	0.64638 (16)	0.22878 (12)	0.35475 (15)	0.0586 (4)
H7	0.6834	0.1886	0.4143	0.070*
C8	0.5648 (2)	0.28496 (14)	0.36371 (19)	0.0752 (5)
H8	0.5471	0.2818	0.4291	0.090*
C9	0.51035 (17)	0.34484 (12)	0.2773 (2)	0.0690 (5)
H9	0.4571	0.3827	0.2850	0.083*
C10	0.53404 (16)	0.34912 (11)	0.17975 (19)	0.0632 (4)
H10	0.4963	0.3893	0.1203	0.076*
C11	0.61498 (15)	0.29289 (10)	0.17013 (16)	0.0538 (4)
H11	0.6309	0.2958	0.1036	0.065*
C12	0.76348 (11)	−0.00201 (8)	0.00198 (13)	0.0448 (3)
C13	0.68438 (16)	−0.06649 (11)	−0.00790 (18)	0.0625 (4)
H13	0.6616	−0.0749	0.0534	0.075*
C14	0.63888 (17)	−0.11863 (11)	−0.1084 (2)	0.0719 (5)
H14	0.5863	−0.1617	−0.1135	0.086*
C15	0.67076 (16)	−0.10715 (11)	−0.19984 (19)	0.0681 (5)
H15	0.6392	−0.1416	−0.2675	0.082*
C16	0.74988 (18)	−0.04419 (12)	−0.19032 (18)	0.0693 (5)
H16	0.7728	−0.0364	−0.2516	0.083*
C17	0.79604 (16)	0.00785 (10)	−0.09063 (15)	0.0578 (4)
H17	0.8498	0.0501	−0.0857	0.069*
C18	1.07172 (12)	0.27042 (8)	0.17789 (12)	0.0411 (3)
C19	1.18800 (14)	0.31368 (11)	0.20301 (17)	0.0606 (4)
H19A	1.2396	0.2764	0.1865	0.091*
H19B	1.2279	0.3303	0.2863	0.091*
H19C	1.1711	0.3621	0.1524	0.091*
C20	1.17574 (11)	0.13205 (8)	0.41606 (11)	0.0382 (3)
C21	1.28104 (14)	0.04085 (11)	0.58940 (16)	0.0602 (4)
C22	1.40213 (17)	0.02732 (16)	0.6959 (2)	0.0910 (8)
H22A	1.3910	0.0001	0.7593	0.137*
H22B	1.4412	0.0802	0.7244	0.137*
H22C	1.4517	−0.0070	0.6723	0.137*
N1	1.07548 (9)	0.21007 (7)	0.25605 (9)	0.0385 (2)
N2	1.18656 (9)	0.19210 (7)	0.35415 (10)	0.0391 (2)
N3	1.27755 (10)	0.10526 (8)	0.51668 (10)	0.0459 (3)
H3	1.3443	0.1316	0.5348	0.055*
S1	0.68373 (3)	0.11763 (2)	0.10259 (3)	0.04552 (11)
S2	1.03376 (3)	0.08660 (2)	0.37248 (3)	0.04760 (12)
O1	0.97614 (9)	0.28782 (7)	0.08854 (9)	0.0496 (2)
O2	1.19260 (12)	−0.00139 (10)	0.56887 (15)	0.0911 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0315 (6)	0.0393 (6)	0.0463 (6)	−0.0006 (5)	0.0128 (5)	−0.0023 (5)
C2	0.0295 (6)	0.0440 (7)	0.0462 (7)	−0.0014 (5)	0.0144 (5)	−0.0066 (5)
C3	0.0275 (5)	0.0391 (6)	0.0415 (6)	−0.0027 (4)	0.0111 (5)	−0.0001 (5)
C4	0.0334 (6)	0.0417 (6)	0.0454 (6)	−0.0017 (5)	0.0169 (5)	−0.0033 (5)
C5	0.0356 (6)	0.0420 (6)	0.0441 (6)	−0.0007 (5)	0.0187 (5)	0.0010 (5)
C6	0.0362 (6)	0.0436 (6)	0.0495 (7)	−0.0049 (5)	0.0228 (5)	−0.0037 (5)
C7	0.0614 (9)	0.0688 (10)	0.0551 (8)	−0.0016 (8)	0.0347 (8)	−0.0018 (7)
C8	0.0779 (12)	0.0931 (14)	0.0782 (12)	−0.0035 (11)	0.0560 (11)	−0.0175 (11)
C9	0.0560 (9)	0.0644 (10)	0.1010 (14)	−0.0014 (8)	0.0481 (10)	−0.0211 (10)
C10	0.0539 (9)	0.0514 (9)	0.0889 (12)	0.0088 (7)	0.0362 (9)	0.0020 (8)
C11	0.0528 (8)	0.0531 (8)	0.0657 (9)	0.0082 (6)	0.0358 (7)	0.0066 (7)
C12	0.0320 (6)	0.0397 (6)	0.0537 (7)	0.0014 (5)	0.0113 (5)	−0.0061 (5)
C13	0.0533 (9)	0.0579 (9)	0.0740 (10)	−0.0153 (7)	0.0267 (8)	−0.0141 (8)
C14	0.0498 (9)	0.0556 (10)	0.0958 (14)	−0.0159 (7)	0.0200 (9)	−0.0223 (9)
C15	0.0498 (9)	0.0622 (10)	0.0776 (11)	0.0029 (7)	0.0156 (8)	−0.0305 (9)
C16	0.0708 (11)	0.0702 (11)	0.0666 (10)	−0.0030 (9)	0.0305 (9)	−0.0223 (9)
C17	0.0576 (9)	0.0522 (8)	0.0635 (9)	−0.0072 (7)	0.0272 (8)	−0.0143 (7)
C18	0.0370 (6)	0.0392 (6)	0.0463 (6)	0.0018 (5)	0.0180 (5)	0.0003 (5)
C19	0.0461 (8)	0.0560 (9)	0.0721 (10)	−0.0088 (7)	0.0198 (7)	0.0140 (7)
C20	0.0289 (5)	0.0389 (6)	0.0415 (6)	−0.0018 (4)	0.0111 (5)	−0.0034 (5)
C21	0.0413 (7)	0.0576 (9)	0.0678 (10)	0.0010 (6)	0.0121 (7)	0.0199 (7)
C22	0.0484 (9)	0.1010 (16)	0.0918 (14)	−0.0008 (10)	0.0032 (9)	0.0505 (13)
N1	0.0269 (5)	0.0415 (5)	0.0417 (5)	−0.0022 (4)	0.0107 (4)	0.0011 (4)
N2	0.0278 (5)	0.0422 (5)	0.0402 (5)	−0.0023 (4)	0.0089 (4)	−0.0015 (4)
N3	0.0308 (5)	0.0494 (6)	0.0463 (6)	−0.0035 (4)	0.0073 (4)	0.0060 (5)
S1	0.02991 (17)	0.0501 (2)	0.0527 (2)	−0.00154 (12)	0.01512 (14)	−0.00724 (14)
S2	0.03201 (17)	0.0476 (2)	0.0523 (2)	−0.00652 (12)	0.00926 (14)	0.00873 (14)
O1	0.0386 (5)	0.0543 (6)	0.0509 (5)	0.0070 (4)	0.0156 (4)	0.0104 (4)
O2	0.0511 (7)	0.0829 (9)	0.1081 (11)	−0.0123 (6)	0.0081 (7)	0.0488 (8)

C1—C12	1.5145 (18)	C12—C13	1.388 (2)
C1—C2	1.5228 (17)	C13—C14	1.391 (3)
C1—S1	1.8292 (13)	C13—H13	0.9300
C1—H1	0.9800	C14—C15	1.368 (3)
C2—C3	1.5337 (17)	C14—H14	0.9300
C2—H2A	0.9700	C15—C16	1.371 (3)
C2—H2B	0.9700	C15—H15	0.9300
C3—N1	1.4937 (15)	C16—C17	1.383 (2)
C3—C4	1.5341 (17)	C16—H16	0.9300
C3—S2	1.8543 (13)	C17—H17	0.9300
C4—C5	1.5297 (17)	C18—O1	1.2324 (16)
C4—H4A	0.9700	C18—N1	1.3541 (17)
C4—H4B	0.9700	C18—C19	1.4941 (19)
C5—C6	1.5140 (18)	C19—H19A	0.9600
C5—S1	1.8268 (13)	C19—H19B	0.9600
C5—H5	0.9800	C19—H19C	0.9600
C6—C11	1.383 (2)	C20—N2	1.2742 (17)
C6—C7	1.3811 (19)	C20—N3	1.3808 (16)
C7—C8	1.391 (3)	C20—S2	1.7427 (12)
C7—H7	0.9300	C21—O2	1.209 (2)
C8—C9	1.368 (3)	C21—N3	1.3577 (19)
C8—H8	0.9300	C21—C22	1.499 (2)
C9—C10	1.366 (3)	C22—H22A	0.9600
C9—H9	0.9300	C22—H22B	0.9600
C10—C11	1.389 (2)	C22—H22C	0.9600
C10—H10	0.9300	N1—N2	1.3924 (14)
C11—H11	0.9300	N3—H3	0.8600
C12—C17	1.384 (2)
C12—C1—C2	114.40 (11)	C17—C12—C13	117.78 (14)
C12—C1—S1	107.39 (8)	C17—C12—C1	122.70 (12)
C2—C1—S1	109.74 (9)	C13—C12—C1	119.52 (14)
C12—C1—H1	108.4	C12—C13—C14	120.71 (17)
C2—C1—H1	108.4	C12—C13—H13	119.6
S1—C1—H1	108.4	C14—C13—H13	119.6
C1—C2—C3	112.51 (11)	C15—C14—C13	120.66 (16)
C1—C2—H2A	109.1	C15—C14—H14	119.7
C3—C2—H2A	109.1	C13—C14—H14	119.7
C1—C2—H2B	109.1	C14—C15—C16	119.07 (16)
C3—C2—H2B	109.1	C14—C15—H15	120.5
H2A—C2—H2B	107.8	C16—C15—H15	120.5
N1—C3—C4	109.89 (10)	C15—C16—C17	120.78 (18)
N1—C3—C2	110.53 (10)	C15—C16—H16	119.6
C4—C3—C2	113.35 (10)	C17—C16—H16	119.6
N1—C3—S2	103.09 (8)	C16—C17—C12	120.99 (16)
C4—C3—S2	110.51 (9)	C16—C17—H17	119.5
C2—C3—S2	108.99 (9)	C12—C17—H17	119.5
C5—C4—C3	114.11 (10)	O1—C18—N1	121.01 (12)
C5—C4—H4A	108.7	O1—C18—C19	121.52 (13)
C3—C4—H4A	108.7	N1—C18—C19	117.46 (12)
C5—C4—H4B	108.7	C18—C19—H19A	109.5
C3—C4—H4B	108.7	C18—C19—H19B	109.5
H4A—C4—H4B	107.6	H19A—C19—H19B	109.5
C6—C5—C4	111.36 (11)	C18—C19—H19C	109.5
C6—C5—S1	107.98 (9)	H19A—C19—H19C	109.5
C4—C5—S1	111.28 (9)	H19B—C19—H19C	109.5
C6—C5—H5	108.7	N2—C20—N3	118.63 (11)
C4—C5—H5	108.7	N2—C20—S2	119.44 (9)
S1—C5—H5	108.7	N3—C20—S2	121.93 (10)
C11—C6—C7	118.41 (14)	O2—C21—N3	121.95 (14)
C11—C6—C5	120.91 (12)	O2—C21—C22	123.48 (16)
C7—C6—C5	120.67 (13)	N3—C21—C22	114.57 (14)
C6—C7—C8	120.03 (17)	C21—C22—H22A	109.5
C6—C7—H7	120.0	C21—C22—H22B	109.5
C8—C7—H7	120.0	H22A—C22—H22B	109.5
C9—C8—C7	120.65 (16)	C21—C22—H22C	109.5
C9—C8—H8	119.7	H22A—C22—H22C	109.5
C7—C8—H8	119.7	H22B—C22—H22C	109.5
C8—C9—C10	120.14 (16)	C18—N1—N2	118.39 (10)
C8—C9—H9	119.9	C18—N1—C3	124.27 (10)
C10—C9—H9	119.9	N2—N1—C3	117.33 (10)
C9—C10—C11	119.39 (17)	C20—N2—N1	110.68 (10)
C9—C10—H10	120.3	C21—N3—C20	125.43 (12)
C11—C10—H10	120.3	C21—N3—H3	117.3
C6—C11—C10	121.36 (15)	C20—N3—H3	117.3
C6—C11—H11	119.3	C5—S1—C1	98.36 (6)
C10—C11—H11	119.3	C20—S2—C3	89.43 (6)
C12—C1—C2—C3	−174.88 (10)	C15—C16—C17—C12	−0.2 (3)
S1—C1—C2—C3	64.36 (12)	C13—C12—C17—C16	0.9 (2)
C1—C2—C3—N1	176.11 (10)	C1—C12—C17—C16	−179.42 (15)
C1—C2—C3—C4	−60.01 (14)	O1—C18—N1—N2	178.81 (12)
C1—C2—C3—S2	63.50 (12)	C19—C18—N1—N2	−0.07 (18)
N1—C3—C4—C5	−179.06 (10)	O1—C18—N1—C3	−0.5 (2)
C2—C3—C4—C5	56.72 (14)	C19—C18—N1—C3	−179.34 (13)
S2—C3—C4—C5	−65.95 (12)	C4—C3—N1—C18	−64.69 (15)
C3—C4—C5—C6	−178.82 (11)	C2—C3—N1—C18	61.15 (15)
C3—C4—C5—S1	−58.29 (13)	S2—C3—N1—C18	177.50 (10)
C4—C5—C6—C11	65.69 (17)	C4—C3—N1—N2	116.04 (12)
S1—C5—C6—C11	−56.76 (15)	C2—C3—N1—N2	−118.12 (11)
C4—C5—C6—C7	−114.40 (15)	S2—C3—N1—N2	−1.78 (12)
S1—C5—C6—C7	123.16 (13)	N3—C20—N2—N1	179.47 (11)
C11—C6—C7—C8	−0.5 (2)	S2—C20—N2—N1	−0.92 (15)
C5—C6—C7—C8	179.61 (16)	C18—N1—N2—C20	−177.50 (11)
C6—C7—C8—C9	−0.5 (3)	C3—N1—N2—C20	1.82 (15)
C7—C8—C9—C10	1.2 (3)	O2—C21—N3—C20	2.4 (3)
C8—C9—C10—C11	−0.8 (3)	C22—C21—N3—C20	−177.33 (18)
C7—C6—C11—C10	0.8 (2)	N2—C20—N3—C21	−178.11 (15)
C5—C6—C11—C10	−179.28 (14)	S2—C20—N3—C21	2.3 (2)
C9—C10—C11—C6	−0.2 (3)	C6—C5—S1—C1	178.14 (9)
C2—C1—C12—C17	−11.55 (19)	C4—C5—S1—C1	55.64 (10)
S1—C1—C12—C17	110.50 (14)	C12—C1—S1—C5	176.47 (9)
C2—C1—C12—C13	168.17 (13)	C2—C1—S1—C5	−58.62 (10)
S1—C1—C12—C13	−69.78 (15)	N2—C20—S2—C3	−0.11 (11)
C17—C12—C13—C14	−0.6 (2)	N3—C20—S2—C3	179.49 (11)
C1—C12—C13—C14	179.65 (15)	N1—C3—S2—C20	0.98 (8)
C12—C13—C14—C15	−0.3 (3)	C4—C3—S2—C20	−116.40 (9)
C13—C14—C15—C16	1.0 (3)	C2—C3—S2—C20	118.42 (9)
C14—C15—C16—C17	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1i	0.86	1.94	2.786 (2)	166
C5—H5···O2ii	0.98	2.49	3.446 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1i	0.86	1.94	2.786 (2)	166
C5—H5⋯O2ii	0.98	2.49	3.446 (2)	163

Symmetry codes: (i) ; (ii) .