(±)-N-[4-Acetyl-5-methyl-5-(4-methyl­cyclo­hex-3-en­yl)-4,5-dihydro-1,3,4-thia­diazol-2-yl]acetamide

Mohammed, T.; Mazoir, N.; Daran, J.-C.; Berraho, M.; Benharref, A.

doi:10.1107/S1600536808004728

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Pages o610-o611

doi:10.1107/S1600536808004728

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(±)-N-[4-Acetyl-5-methyl-5-(4-methylcyclohex-3-enyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide

Tebbaa Mohammed,^a Noureddine Mazoir,^a Jean-Claude Daran,^b ^* Moha Berraho ^a and Ahmed Benharref ^a

^aLaboratoire de Chimie Biomoléculaire, Substances Naturelles et Réactivité, Faculté des Sciences, Semlalia, Université Cadi Ayyad, BP 2390 Marrakech, Morocco, and ^bLaboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, France
^*Correspondence e-mail: daran@lcc-toulouse.fr

(Received 11 February 2008; accepted 18 February 2008; online 20 February 2008)

The new title thiadiazole compound, C₁₄H₂₁N₃O₂S, was semi-synthesized starting from 1-(4-methylcyclohex-3-enyl)ethanone, a natural product isolated from Cedrus atlantica essential oil. The stereochemistry has been confirmed by single-crystal X-ray diffraction. The thiadiazoline ring is roughly planar, although it may be regarded as having a half-chair conformation. The cyclohexenyl ring has a half-chair conformation. The most interesting feature is the formation of a pseudo-ring formed by four molecules associated through N—H⋯O hydrogen bonds around a fourfold inversion axis, forming an R₄⁴(28) motif.

Related literature

For related literature, see: Aly et al. (2007 ); Beatriz et al. (2002 ); Bernstein et al. (1995 ); Cremer & Pople (1975 ); Demirbas et al. (2005 ); Etter et al. (1990 ); Farghaly et al. (2006 ); Invidiata et al. (1996 ); Kubota et al. (1982 ); Nizamuddin et al. (1999 ); Ourhriss et al. (2005 ); Paolo et al. (2005 ); Radul et al. (2005 ); Sun et al. (1999 ); Udupi et al. (2000 ).

Experimental

Crystal data

C₁₄H₂₁N₃O₂S
M_r = 295.40
Tetragonal, I 4₁ /a
a = 16.6855 (3) Å
c = 21.8961 (8) Å
V = 6096.0 (3) Å³
Z = 16
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 180 (2) K
0.29 × 0.24 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: none
87517 measured reflections
4637 independent reflections
3849 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.113
S = 1.11
4637 reflections
185 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1ⁱ	0.88	1.95	2.8223 (14)	171
Symmetry code: (i) $[y+{\script{1\over 4}}, -x+{\script{7\over 4}}, -z+{\script{3\over 4}}]$ .

Data collection: APEX2 (Bruker, 2006 ); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and CAMERON (Watkin et al., 1993 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004728/bg2164sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808004728/bg2164Isup2.hkl

checkCIF report

Comment top

Thiadiazolic compounds have beenreported in a large number of papers (Beatriz et al., 2002, Farghaly et al., 2006). These compounds are associated with diverse biological activities. Likewise, the 1,3,4-thiadiazoles nuclei which incorporate toxiphoric –N=C—S– linkage possess anti-inflammatory (Udupi et al., 2000), herbicidal (Nizamuddin et al., 1999), antimicrobial (Demirbas et al., 2005) bactericidal (Sun et al., 1999) and anti-HIV-1 properties(Invidiata et al., 1996).

In this connection, the chemical modification of a natural product isolated from Cedrus atlantica essential oil, 1-(4-methylcyclohex-3-enyl) ethanone, using thiosemicarbazide (Paolo et al., 2005; Ourhriss et al., 2005; Aly et al., 2007) followed by treatment of acetic anhydride and pyridine yielded the 1,3,4-thiadiazolic compound (II) with a good yield and high chimiospecifity.

The structure of (II) was established by ¹H and ¹³CNMR and confirmed by its single-Crystal X-ray structure (Fig. 1).

The thiadiazoline ring may be regarded as having a half-chair conformation with puckering parameters Q= 0.184 (1) Å and ϕ= 34.1 (4)° (Cremer & Pople, 1975); however it could be also considered as roughly planar with the largest deviation from the mean plane being -0.1069 (8) Å at N1. Such conformation is usual for thiadiazoline rings (Kubota et al., 1982; Radul et al., 2005). The cyclohexenyl ring has a half-chair conformation with puckering parameters Q=0.489 (2) Å, θ= 49.5 (2)° and ϕ= 344.8 (3)°.

The most interesting feature is the formation of a pseudo ring formed by four molecules associated through N—H···O hydrogen bonds around a fourfold screw axis (Fig. 2, Table 1) so completing a R₄⁴(28) motif (Etter et al., 1990; Bernstein et al., 1995).

Related literature top

For related literature, see: Aly et al. (2007); Beatriz et al. (2002); Bernstein et al. (1995); Cremer & Pople (1975); Demirbas et al. (2005); Etter et al. (1990); Farghaly et al. (2006); Invidiata et al. (1996); Kubota et al. (1982); Nizamuddin et al. (1999); Ourhriss et al. (2005); Paolo et al. (2005); Radul et al. (2005); Sun et al. (1999); Udupi et al. (2000).

Experimental top

To a solution of an equimolecular quantity of compound (I) and thiosemicarbazide dissolved in ethanol, several drops of HCl (c) were added. The reactional mixture was heated at reflux during 5 h and then evaporated under reduced pressure. The residue obtained was analysed on silica gel column with hexane: ethyl acetate (95:5) as an eluent. 0.25 mmol of the thiosemicarbazone obtained was dissolved in 2 ml of pyridine and 2 ml of acetic anhydride. The mixture was heated at reflux during 1 h with magnetic stirring, and then evaporated under reduced pressure. The residue obtained was purified on a silicagel column using hexane-ethyl acetate (90:10) as an eluent yielded compound (II) in 60% yield. Suitable crystals were obtained by evaporation of a dichloromethane solution at 277 K. m.p.= 483–484 K (dichloromethane); Spectroscopic analysis: ¹H NMR (300 MHz, CDCl₃) δ (p.p.m.): 9.49 (NH, s), 1.80 (3H2, s), 2.07 (1H1', m), 5.57 (1H3', dd, J₁ = 10 Hz, J₂ = 6 Hz), 1.58 (3H-7', s), 2.13, 2.27 (CH₃CO, 2 s); ¹³C NMR (75 MHz, CDCl₃) δ (p.p.m.): 85.4 (C-1), 19.2 (C-2), 36.7 (C-1'), 26.2 (C-2'), 118.1 (C-3'), 132.7 (C-4'), 28.2 (C-5'), 23.0 (C-6'), 22.2 (C-7'), 158.1 (C=N), 169.5, 170.4 (COCH₃), 22.6, 24.5 (COCH₃).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006; data reduction: APEX2 (Bruker, 2006; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular view of compound (II), showing the atom-labelling scheme. Ellipsoids are drawn at the 50% probability level.
	Fig. 2. Projection down the c axis, showing the formation of the R₄⁴(28) motif through N—H···O hydrogen bonds around the fourfold screw axis 4. H atoms not involved in hydrogen bonding have been omitted for clarity.
	Fig. 3. The formation of the title compound.

(±)-N-[4-Acetyl-5-methyl-5-(4-methylcyclohex-3-enyl)-4,5-dihydro-\1,3,4-thiadiazol-2-yl]acetamide top

Crystal data top

C₁₄H₂₁N₃O₂S	D_x = 1.287 Mg m⁻³
M_r = 295.40	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 9915 reflections
Hall symbol: -I 4ad	θ = 2.5–36.1°
a = 16.6855 (3) Å	µ = 0.22 mm⁻¹
c = 21.8961 (8) Å	T = 180 K
V = 6096.0 (3) Å³	Platelet, colourless
Z = 16	0.29 × 0.24 × 0.08 mm
F(000) = 2528

Data collection top

Bruker APEXII CCD area-detector diffractometer	3849 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 30.5°, θ_min = 2.4°
ϕ and ω scans	h = −23→23
87517 measured reflections	k = −23→23
4637 independent reflections	l = −31→31

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0505P)² + 5.869P] where P = (F_o² + 2F_c²)/3
4637 reflections	(Δ/σ)_max = 0.001
185 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₄H₂₁N₃O₂S	Z = 16
M_r = 295.40	Mo Kα radiation
Tetragonal, I4₁/a	µ = 0.22 mm⁻¹
a = 16.6855 (3) Å	T = 180 K
c = 21.8961 (8) Å	0.29 × 0.24 × 0.08 mm
V = 6096.0 (3) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3849 reflections with I > 2σ(I)
87517 measured reflections	R_int = 0.032
4637 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.11	Δρ_max = 0.39 e Å⁻³
4637 reflections	Δρ_min = −0.26 e Å⁻³
185 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	0.65060 (7)	0.64068 (7)	0.33934 (6)	0.0214 (2)
C2	0.64575 (8)	0.56723 (8)	0.29765 (6)	0.0287 (3)
H2A	0.6800	0.5755	0.2618	0.043*
H2B	0.5902	0.5594	0.2844	0.043*
H2C	0.6639	0.5197	0.3200	0.043*
C3	0.68632 (7)	0.78535 (7)	0.31834 (6)	0.0211 (2)
C11	0.79352 (7)	0.62428 (7)	0.37378 (6)	0.0235 (2)
C12	0.87096 (7)	0.66585 (8)	0.38792 (7)	0.0281 (3)
H12A	0.9094	0.6270	0.4043	0.042*
H12B	0.8615	0.7081	0.4182	0.042*
H12C	0.8926	0.6897	0.3505	0.042*
C31	0.62901 (8)	0.90880 (8)	0.27886 (6)	0.0270 (2)
C32	0.64169 (10)	0.99767 (9)	0.27574 (10)	0.0446 (4)
H32A	0.6634	1.0120	0.2356	0.067*
H32B	0.6796	1.0140	0.3076	0.067*
H32C	0.5904	1.0252	0.2820	0.067*
C1'	0.61004 (7)	0.62529 (7)	0.40168 (6)	0.0230 (2)
H1'	0.6342	0.5754	0.4190	0.028*
C2'	0.52001 (8)	0.61027 (9)	0.39510 (6)	0.0298 (3)
H2E	0.4950	0.6567	0.3743	0.036*
H2F	0.5114	0.5624	0.3693	0.036*
C3'	0.47984 (9)	0.59770 (10)	0.45606 (7)	0.0360 (3)
H3'	0.4307	0.5690	0.4578	0.043*
C4'	0.51280 (9)	0.62689 (10)	0.50920 (7)	0.0351 (3)
C5'	0.58895 (11)	0.66893 (12)	0.50955 (7)	0.0433 (4)
H5A	0.6287	0.6349	0.5309	0.052*
H5B	0.5825	0.7184	0.5340	0.052*
C6'	0.62334 (9)	0.69185 (9)	0.44820 (6)	0.0309 (3)
H6A	0.6815	0.7023	0.4524	0.037*
H6B	0.5975	0.7417	0.4336	0.037*
C7'	0.47125 (12)	0.61447 (13)	0.56956 (8)	0.0504 (4)
H71	0.4231	0.5818	0.5634	0.076*
H72	0.4561	0.6665	0.5867	0.076*
H73	0.5076	0.5869	0.5978	0.076*
S1	0.604309 (17)	0.726031 (18)	0.298610 (14)	0.02284 (9)
O1	0.78216 (6)	0.55218 (6)	0.38435 (5)	0.0313 (2)
O2	0.57194 (6)	0.87583 (6)	0.25536 (5)	0.0338 (2)
N1	0.73445 (6)	0.66905 (6)	0.34821 (5)	0.0224 (2)
N2	0.74763 (6)	0.75163 (6)	0.34255 (5)	0.0231 (2)
N3	0.68691 (6)	0.86761 (6)	0.31029 (5)	0.0251 (2)
H3	0.7268	0.8951	0.3263	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0182 (5)	0.0197 (5)	0.0262 (5)	−0.0009 (4)	−0.0014 (4)	−0.0010 (4)
C2	0.0296 (6)	0.0251 (6)	0.0312 (6)	−0.0016 (5)	−0.0005 (5)	−0.0063 (5)
C3	0.0177 (5)	0.0211 (5)	0.0245 (5)	−0.0012 (4)	0.0000 (4)	0.0011 (4)
C11	0.0200 (5)	0.0228 (5)	0.0277 (6)	0.0034 (4)	−0.0003 (4)	0.0000 (4)
C12	0.0202 (5)	0.0264 (6)	0.0376 (7)	0.0022 (4)	−0.0047 (5)	0.0019 (5)
C31	0.0242 (6)	0.0267 (6)	0.0302 (6)	0.0032 (4)	0.0007 (5)	0.0060 (5)
C32	0.0397 (8)	0.0253 (7)	0.0687 (12)	0.0039 (6)	−0.0089 (8)	0.0114 (7)
C1'	0.0211 (5)	0.0236 (5)	0.0244 (5)	−0.0011 (4)	−0.0006 (4)	0.0008 (4)
C2'	0.0239 (6)	0.0370 (7)	0.0287 (6)	−0.0066 (5)	−0.0005 (5)	0.0027 (5)
C3'	0.0288 (7)	0.0432 (8)	0.0359 (7)	−0.0025 (6)	0.0059 (5)	0.0077 (6)
C4'	0.0340 (7)	0.0396 (8)	0.0318 (7)	0.0040 (6)	0.0066 (6)	0.0060 (6)
C5'	0.0507 (9)	0.0514 (9)	0.0278 (7)	−0.0088 (7)	0.0052 (6)	−0.0059 (6)
C6'	0.0320 (7)	0.0322 (7)	0.0286 (6)	−0.0054 (5)	0.0009 (5)	−0.0046 (5)
C7'	0.0547 (11)	0.0607 (11)	0.0360 (8)	−0.0001 (9)	0.0146 (8)	0.0057 (8)
S1	0.01844 (14)	0.02350 (15)	0.02657 (15)	−0.00176 (10)	−0.00422 (10)	0.00242 (10)
O1	0.0263 (4)	0.0217 (4)	0.0460 (6)	0.0025 (3)	−0.0046 (4)	0.0038 (4)
O2	0.0284 (5)	0.0368 (5)	0.0361 (5)	0.0003 (4)	−0.0088 (4)	0.0073 (4)
N1	0.0171 (4)	0.0185 (4)	0.0316 (5)	0.0000 (3)	−0.0017 (4)	0.0015 (4)
N2	0.0183 (4)	0.0195 (4)	0.0314 (5)	−0.0011 (3)	−0.0014 (4)	0.0024 (4)
N3	0.0200 (5)	0.0208 (5)	0.0345 (6)	−0.0007 (4)	−0.0038 (4)	0.0035 (4)

Geometric parameters (Å, º) top

C1—N1	1.4897 (15)	C32—H32C	0.9800
C1—C2	1.5303 (17)	C1'—C6'	1.5232 (18)
C1—C1'	1.5451 (17)	C1'—C2'	1.5298 (17)
C1—S1	1.8493 (12)	C1'—H1'	1.0000
C2—H2A	0.9800	C2'—C3'	1.508 (2)
C2—H2B	0.9800	C2'—H2E	0.9900
C2—H2C	0.9800	C2'—H2F	0.9900
C3—N2	1.2822 (15)	C3'—C4'	1.376 (2)
C3—N3	1.3839 (15)	C3'—H3'	0.9500
C3—S1	1.7431 (12)	C4'—C5'	1.451 (2)
C11—O1	1.2396 (15)	C4'—C7'	1.507 (2)
C11—N1	1.3577 (15)	C5'—C6'	1.510 (2)
C11—C12	1.4987 (18)	C5'—H5A	0.9900
C12—H12A	0.9800	C5'—H5B	0.9900
C12—H12B	0.9800	C6'—H6A	0.9900
C12—H12C	0.9800	C6'—H6B	0.9900
C31—O2	1.2141 (17)	C7'—H71	0.9800
C31—N3	1.3710 (16)	C7'—H72	0.9800
C31—C32	1.499 (2)	C7'—H73	0.9800
C32—H32A	0.9800	N1—N2	1.4009 (14)
C32—H32B	0.9800	N3—H3	0.8800

N1—C1—C2	112.45 (10)	C3'—C2'—C1'	112.07 (12)
N1—C1—C1'	110.42 (10)	C3'—C2'—H2E	109.2
C2—C1—C1'	111.76 (10)	C1'—C2'—H2E	109.2
N1—C1—S1	102.15 (7)	C3'—C2'—H2F	109.2
C2—C1—S1	107.88 (9)	C1'—C2'—H2F	109.2
C1'—C1—S1	111.79 (8)	H2E—C2'—H2F	107.9
C1—C2—H2A	109.5	C4'—C3'—C2'	121.44 (13)
C1—C2—H2B	109.5	C4'—C3'—H3'	119.3
H2A—C2—H2B	109.5	C2'—C3'—H3'	119.3
C1—C2—H2C	109.5	C3'—C4'—C5'	121.69 (14)
H2A—C2—H2C	109.5	C3'—C4'—C7'	120.61 (15)
H2B—C2—H2C	109.5	C5'—C4'—C7'	117.69 (15)
N2—C3—N3	118.82 (11)	C4'—C5'—C6'	116.78 (14)
N2—C3—S1	118.67 (9)	C4'—C5'—H5A	108.1
N3—C3—S1	122.49 (9)	C6'—C5'—H5A	108.1
O1—C11—N1	119.99 (11)	C4'—C5'—H5B	108.1
O1—C11—C12	122.86 (11)	C6'—C5'—H5B	108.1
N1—C11—C12	117.15 (11)	H5A—C5'—H5B	107.3
C11—C12—H12A	109.5	C5'—C6'—C1'	110.78 (12)
C11—C12—H12B	109.5	C5'—C6'—H6A	109.5
H12A—C12—H12B	109.5	C1'—C6'—H6A	109.5
C11—C12—H12C	109.5	C5'—C6'—H6B	109.5
H12A—C12—H12C	109.5	C1'—C6'—H6B	109.5
H12B—C12—H12C	109.5	H6A—C6'—H6B	108.1
O2—C31—N3	122.57 (12)	C4'—C7'—H71	109.5
O2—C31—C32	122.65 (13)	C4'—C7'—H72	109.5
N3—C31—C32	114.79 (12)	H71—C7'—H72	109.5
C31—C32—H32A	109.5	C4'—C7'—H73	109.5
C31—C32—H32B	109.5	H71—C7'—H73	109.5
H32A—C32—H32B	109.5	H72—C7'—H73	109.5
C31—C32—H32C	109.5	C3—S1—C1	89.42 (5)
H32A—C32—H32C	109.5	C11—N1—N2	117.63 (10)
H32B—C32—H32C	109.5	C11—N1—C1	124.11 (10)
C6'—C1'—C2'	109.00 (11)	N2—N1—C1	116.65 (9)
C6'—C1'—C1	113.93 (10)	C3—N2—N1	110.05 (10)
C2'—C1'—C1	111.97 (10)	C31—N3—C3	123.79 (11)
C6'—C1'—H1'	107.2	C31—N3—H3	118.1
C2'—C1'—H1'	107.2	C3—N3—H3	118.1
C1—C1'—H1'	107.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.88	1.95	2.8223 (14)	171

Symmetry code: (i) y+1/4, −x+7/4, −z+3/4.

Experimental details

Crystal data
Chemical formula	C₁₄H₂₁N₃O₂S
M_r	295.40
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	180
a, c (Å)	16.6855 (3), 21.8961 (8)
V (Å³)	6096.0 (3)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.29 × 0.24 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	87517, 4637, 3849
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.714

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.113, 1.11
No. of reflections	4637
No. of parameters	185
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.26

Computer programs: APEX2 (Bruker, 2006), APEX2 (Bruker, 2006, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.88	1.95	2.8223 (14)	171.0

Symmetry code: (i) y+1/4, −x+7/4, −z+3/4.

Acknowledgements

The authors thank Professor Abdelkader Mokhlisse for fruitful discussions.

References

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Pages o610-o611

doi:10.1107/S1600536808004728

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

(±)-N-[4-Acetyl-5-methyl-5-(4-methyl­cyclo­hex-3-en­yl)-4,5-di­hydro-1,3,4-thia­diazol-2-yl]acetamide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(±)-N-[4-Acetyl-5-methyl-5-(4-methylcyclohex-3-enyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide