N-(1-Acetyl-r-7,c-9-diphenyl-4,8-dithia-1,2-diaza­spiro­[5.4]dec-2-en-3-yl)acet­amide

Gayathri, D.; Velmurugan, D.; Umamatheswari, S.; Kabilan, S.; Ravikumar, K.

doi:10.1107/S1600536808001025

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Pages o494-o495

doi:10.1107/S1600536808001025

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N-(1-Acetyl-r-7,c-9-diphenyl-4,8-dithia-1,2-diazaspiro[5.4]dec-2-en-3-yl)acetamide

D. Gayathri,^a D. Velmurugan,^a ^* S. Umamatheswari,^b S. Kabilan ^b and K. Ravikumar ^c

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, ^bDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, India, and ^cLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India
^*Correspondence e-mail: d_velu@yahoo.com

(Received 16 December 2007; accepted 10 January 2008; online 23 January 2008)

In the title compound, C₂₂H₂₃N₃O₂S₂, the five-membered ring is planar and the C₅S ring adopts a chair conformation. The crystal packing is stabilized by intermolecular N—H⋯O and C—H⋯O interactions, 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_r = 425.55
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.116
S = 0.97
5139 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+2, -y, -z+1.

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/S1600536808001025/at2527sup1.cif

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

checkCIF report

Comment top

Tetrahydrothiopyrans play major roles in the field of medicinal chemistry (Isaac et al., 2003). 1,3,4-Thiadiazoline nucleus, a biologically active heterocyclic ring, is also associated with a wide range of pharmacological activities (Pan et al., 2003; Jung et al., 2004; Foroumadi et al., 2002; Jalilian et al., 2002; Leung-Toung et al., 2003). An essential component of the search for new leads in a drug-design programme is the synthesis of molecules, which is novel and resembles known biologically active molecules by virtue of the presence of certain pharmocophoric groups. Certain small heterocyclic molecules act as highly functionalized scaffolds and are pharmacophores of a number of biologically active and medicinally useful molecules. As the title compound (I) is of much biological importance, we have undertaken the crystal structure determination by X-ray diffraction.

The bond lengths and bond angles in (I) are comparable with those in the literature (Allen et al., 1987). The sum of the bond angles around N1 atom [360.0 (3)°] indicates the sp² hybridization. The torsion angles C19—C18—N1—N2 [-0.1 (2)°) and C19—C18—N1—C3 [-179.3 (1)°] indicate that atoms C18 and C19 lie in the plane of the five membered ring (N1/N2/C20/S2/C3). Also the torsion angles C22—C21—N3—C20 [-177.3 (2)°], O2—C21—N3—C20 [2.4 (3)°], C21—N3—C20—S2 [2.3 (2)°] and C21—N3—C20—N2 [-178.1 (2)°] indicate that the substituted moiety at C20 lie in the plane of the ring to which it is attached. The dihedral angle between the two phenyl rings in the structure is about 77.6 (1)° which clearly indicates that the two phenyl rings are nearly perpendicular to each other.

The six membered ring C1—C5/S1 adopts chair conformation with the puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) being q₂ = 0.117 (1) Å, q₃ = 0.651 (1) Å; Q_T = 0.661 (1)Å and θ = 10.2 (1)°.

The crystal packing is stabilized N—H···O and C—H···O intermolecular interaction generating a chain of C(7) and a centrosymmetric dimer of R₂²(18) ring, respectively.

Related literature top

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 top

2,6-Diphenyltetrahydrothiopyran-4-one thiosemicarbazone (0.025 mol) was treated with freshly distilled acetic anhydride and the mixture was refluxed for 8 h on a water bath (363–373 K). The removal of solvent from the cooled reaction mixture in vaccuo afforded 4-acetyl-2-acetylamino-5-spiro-((r)-2,(c)6-diphenyltetrahydrothiopyran-4-yl)- 4,5-dihydro-[1,3,4]thiadiazole which was purified in neutral alumina column using n-hexane-ethyl acetate (4:1) as eluent. The pure compound was recrystallized from ethanol [m.p.: 399 K].

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 (I), with atom labels and 30% probability displacement ellipsoids.
	Fig. 2. The packing of (I), viewed down the a axis, showing N—H···O and C—H···O intermolecular interactions. H atoms not involved in hydrogen bonding have been omitted.

N-(1-Acetyl-r-7,c-9-diphenyl-4,8-dithia-1,2-diazaspiro[5.4]dec-2-en-3- yl)acetamide top

Crystal data top

C₂₂H₂₃N₃O₂S₂	F(000) = 896
M_r = 425.55	D_x = 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 = 1.9–28.0°
b = 16.0218 (9) Å	µ = 0.27 mm⁻¹
c = 12.3852 (7) Å	T = 293 K
β = 116.714 (1)°	Block, colourless
V = 2185.7 (2) Å³	0.25 × 0.24 × 0.22 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4587 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 28.0°, θ_min = 1.9°
ω scans	h = −15→15
24434 measured reflections	k = −21→21
5139 independent reflections	l = −16→16

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0759P)² + 0.4937P] where P = (F_o² + 2F_c²)/3
5139 reflections	(Δ/σ)_max = 0.031
264 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₂H₂₃N₃O₂S₂	V = 2185.7 (2) Å³
M_r = 425.55	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.3310 (7) Å	µ = 0.27 mm⁻¹
b = 16.0218 (9) Å	T = 293 K
c = 12.3852 (7) Å	0.25 × 0.24 × 0.22 mm
β = 116.714 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4587 reflections with I > 2σ(I)
24434 measured reflections	R_int = 0.020
5139 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 0.97	Δρ_max = 0.31 e Å⁻³
5139 reflections	Δρ_min = −0.17 e Å⁻³
264 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	0.81098 (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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, z+1/2; (ii) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₃N₃O₂S₂
M_r	425.55
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	12.3310 (7), 16.0218 (9), 12.3852 (7)
β (°)	116.714 (1)
V (Å³)	2185.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.25 × 0.24 × 0.22

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	24434, 5139, 4587
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.116, 0.97
No. of reflections	5139
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.17

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
N3—H3···O1ⁱ	0.86	1.94	2.786 (2)	165.9
C5—H5···O2ⁱⁱ	0.98	2.49	3.446 (2)	163.4

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

Acknowledgements

DG thanks CSIR, India, for the award of a Senior Research Fellowship. DV thanks DST, India, for a major research project, and acknowledges the Department of Science and Technology (DST-FIST) and the University Grants Commission (UGC), Government of India, for the provision of research facilities.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2001). SMART and SAINT. 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
Foroumadi, A., Asadipour, A., Mirzaei, M., Karimi, J. & Emami, S. (2002). II Farmaco, 57, 765–769. Web of Science CrossRef CAS Google Scholar
Isaac, M., Slassi, M., Xin, T., Arora, J., O'Brien, A., Edwards, L., MacLean, N., Wilson, J., Demschyshyn, L., Labrie, P., Naismith, A., Maddaford, S. P., Papac, D., Harrison, S., Wang, H., Draper, S. & Tehim, A. (2003). Bioorg. Med. Chem. Lett. 13, 4409–4413. Web of Science CrossRef PubMed CAS Google Scholar
Jalilian, A. R., Sattari, S., Bineshmarvasti, M., Daneshtalab, M. & Shafiee, A. (2002). II Farmaco, 58, 63–68. CrossRef Google Scholar
Jung, K. Y., Kim, S. K., Gao, Z. G., Gross, A. S., Melman, N., Jacobson, K. A. & Kim, Y. C. (2004). Bioorg. Med. Chem. 12, 613–623. Web of Science CrossRef PubMed CAS Google Scholar
Leung-Toung, R., Odzinska, J., Li, W., Lowrie, J., Kukreja, R., Desilets, D., Karimian, K. & Tam, T. F. (2003). Bioorg. Med. Chem. 11, 5529–5537. Web of Science CrossRef PubMed CAS 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
Pan, K., Scott, M. K., Lee, D. H. S., Fitzpatric, L. J., Crooke, J. J., Rivero, R. A., Rosenthal, D. I., Vaidya, A. H., Zhao, B. & Reiz, A. B. (2003). Bioorg. Med. Chem. 11, 185–192. Web of Science CrossRef PubMed CAS Google Scholar
Schmidt, P., Eichenberger, K. & Schwiezer, E. (1970). Chem. Abstr. 72, 318377u. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, U., Raju, B., Lam, S., Zhou, J., Gadwood, R. C., Ford, C. W., Zurenko, G. E., Schaadt, R. D., Morin, S. E., Adams, W. J., Friis, J. M., Courtney, M., Palandra, J., Hackbarth, C. J., Lopez, S. et al. (2003). Bioorg. Med. Chem. Lett. 13, 4209–4212. Web of Science CrossRef PubMed CAS Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 2| February 2008| Pages o494-o495

doi:10.1107/S1600536808001025

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

N-(1-Acetyl-r-7,c-9-di­phenyl-4,8-di­thia-1,2-di­aza­spiro­[5.4]dec-2-en-3-yl)acet­amide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-(1-Acetyl-r-7,c-9-diphenyl-4,8-dithia-1,2-diazaspiro[5.4]dec-2-en-3-yl)acetamide