N-[4-Acetyl-5-(2-methylprop-1-enyl)-5-(2-p-tolyl­prop­yl)-4,5-dihydro-1,3,4-thia­diazol-2-yl]acetamide

Mazoir, N.; El Ammari, L.; Bouhmaida, N.; Dahaoui, S.; Benharref, A.; Berraho, M.

doi:10.1107/S1600536809017127

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Pages o1269-o1270

doi:10.1107/S1600536809017127

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N-[4-Acetyl-5-(2-methylprop-1-enyl)-5-(2-p-tolylpropyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide

Noureddine Mazoir,^a Lahcen El Ammari,^b Nouzha Bouhmaida,^c Slimane Dahaoui,^d Ahmed Benharref ^a and Moha Berraho ^a ^*

^aLaboratoire de Chimie Biomoléculaires, Substances Naturelles et Réactivité, Faculté des Sciences Semlalia, BP 2390, Bd My Abdellah, 40000 Marrakech, Morocco, ^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Avenue Ibn Battouta, BP 1014, Rabat, Morocco, ^cLaboratoire des Sciences des Matériaux, Département de Physique, Faculté des Sciences Semlalia, BP 2390, Bd My Abdellah, 40000 Marrakech, Morocco, and ^dCRM2 (UMR UHP - CNRS 7036), Faculté des Sciences et Techniques, BP 70239, Bd des Aiguillettes, 54506 Vandoeuvre-lès-Nancy CEDEX, France
^*Correspondence e-mail: mberraho@yahoo.fr

(Received 3 May 2009; accepted 6 May 2009; online 14 May 2009)

The title heterocyclic compound, C₂₀H₂₇N₃O₂S, was synthesized from 2-(4-methylcyclohex-3-enyl)-6-methylhepta-2,5-dien-4-one, which was isolated from the essential oil Cedrus atlantica. The thiadiazole ring is essentially planar [maximum deviation 0.006 (2) Å] and it forms a dihedral angle of 18.08 (9)° with the benzene ring. The dihedral angle between the thiadiazole ring and the acetamide plane is 7.62 (10)°. In the crystal, molecules are linked into chains running along the c axis by intermolecular N—H⋯O hydrogen bonds.

Related literature

For the biological activity of 1,3,4-thiadiazole derivatives, see: Demirbas et al. (2005 ); Holla et al. (2002 ); Kritsanida et al. (2002 ); Nizamuddin et al. (1999 ); Sun et al. (1999 ); Udupi et al. (2000 ). For the synthesis, see: Beatriz et al. (2002 ); Sakthivel et al. (2008 ). For related structures, see: Loughzail et al. (2009 ); Tebaa et al. (2009 ).

Experimental

Crystal data

C₂₀H₂₇N₃O₂S
M_r = 373.51
Monoclinic, P 2₁ /c
a = 10.855 (2) Å
b = 14.193 (2) Å
c = 12.854 (4) Å
β = 90.955 (11)°
V = 1980.1 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 100 K
0.28 × 0.17 × 0.12 mm

Data collection

Bruker X8 APEX CCD area-detector diffractometer
Absorption correction: none
7884 measured reflections
4030 independent reflections
3365 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.094
S = 1.10
4030 reflections
249 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2⋯O2ⁱ	0.87 (2)	1.96 (2)	2.811 (2)	167 (2)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017127/ci2797sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017127/ci2797Isup2.hkl

checkCIF report

Comment top

1,3,4-Thiadiazole derivatives possess antimicrobial (Demirbas et al., 2005) and antiviral (Kritsanida et al., 2002) activities. They are also known for their broad-spectrum of biological activities such as antibacterial (Sun et al., 1999), anti-inflammatory (Udupi et al., 2000) and herbicidal (Nizamuddin et al., 1999). In addition, [1,3,4]thiadiazoles exhibit various biological activities possibly due to the presence of the ═ N—C—S moiety (Holla et al., 2002). In view of these findings and in continuation to our previous work on the synthesis of [1,3,4]thiadiazoles, we report herein the hemisynthesis of N-[4-acetyl-5-isobutenyl-5-(2-p-tolylpropyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide, (I), through chemical modification of 2-(4-methylcyclohex-3-enyl)-6-methylhepta-2,5-dien-4-one, which is isolated from Cedrus Atlantica essential oil. Thus, aromatization of this later, followed by condensation with thiosemicarbazide (Beatriz et al., 2002; Sakthivel et al., 2008) ending with treatment of acetic anhydride in the presence of pyridine yielded the diasterioisomers in high stereoselectivity.

The molecular structure of (I) is shown in Fig. 1. The geometric parameters (bond lengths and angles) are very similar to those observed in previously reported structures (Loughzail et al.,2009; Tebaa et al.,2009). The thiadiazole ring system is essentially planar and it forms a dihedral angle of 18.08 (9)° with the benzene ring.

In the crystal structure, molecules are linked into chains (Fig. 2) running along the c axis by intermolecular N—H···O hydrogen bonds (Table 1) involving the carbonyl and the acetamide groups.

Related literature top

For the biological activity of 1,3,4-thiadiazole derivatives, see: Demirbas et al. (2005); Holla et al. (2002); Kritsanida et al. (2002); Nizamuddin et al. (1999); Sun et al. (1999); Udupi et al. (2000). For the synthesis, see: Beatriz et al. (2002); Sakthivel et al. (2008). For related structures, see: Loughzail et al. (2009); Tebaa et al. (2009).

Experimental top

A mixture of 2-(4-methylcyclohex-3-enyl)-6-methylhepta-2,5-dien-4-one (0.5 g, 2.3 mmol) and Pd/C (10%) was heated at 423 K for 12 h. The product obtained was treated with equimolecular quantity of thiosemicarbazide and several drops of HCl were added. The reactional mixture was heated at reflux in ethanol for 5 h and then evaporated under reduced pressure and the residue obtained was purified on silica gel column using hexane–ethyl acetate (96:4) as an eluent. 0.25 mmol of the thiosemicarbazone obtained was dissolved in 2.5 ml of pyridine and 2.5 ml of acetic anhydride. The mixture was heated on a water bath for 1.5 h. The resulting residue was concentrated in vacuo and chromatographied on silica gel column with hexane–ethyl acetate (92:8) as an eluent. Suitable crystals were obtained by evaporation of an ethyl acetate solution at 277 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound, with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Partial packing view showing the N—H···O hydrogen bonds (dashed lines) and the formation of a chain along the c axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

N-[4-Acetyl-5-(2-methylprop-1-enyl)-5-(2-p-tolylpropyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide top

Crystal data top

C₂₀H₂₇N₃O₂S	F(000) = 800
M_r = 373.51	D_x = 1.253 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8068 reflections
a = 10.855 (2) Å	θ = 2.8–26.4°
b = 14.193 (2) Å	µ = 0.18 mm⁻¹
c = 12.854 (4) Å	T = 100 K
β = 90.955 (11)°	Prism, colourless
V = 1980.1 (8) Å³	0.28 × 0.17 × 0.12 mm
Z = 4

Data collection top

Bruker X8 APEX CCD area-detector diffractometer	3365 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 26.4°, θ_min = 2.8°
ϕ and ω scans	h = 0→13
7884 measured reflections	k = −17→17
4030 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0257P)² + 1.5568P] where P = (F_o² + 2F_c²)/3
4030 reflections	(Δ/σ)_max = 0.001
249 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₀H₂₇N₃O₂S	V = 1980.1 (8) Å³
M_r = 373.51	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.855 (2) Å	µ = 0.18 mm⁻¹
b = 14.193 (2) Å	T = 100 K
c = 12.854 (4) Å	0.28 × 0.17 × 0.12 mm
β = 90.955 (11)°

Data collection top

Bruker X8 APEX CCD area-detector diffractometer	3365 reflections with I > 2σ(I)
7884 measured reflections	R_int = 0.032
4030 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.24 e Å⁻³
4030 reflections	Δρ_min = −0.20 e Å⁻³
249 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
H2	0.357 (2)	0.0915 (17)	0.0811 (19)	0.039 (7)*
H9	0.5323 (18)	0.1563 (13)	0.5491 (16)	0.018 (5)*
C1'	0.04998 (19)	0.36320 (14)	0.44410 (16)	0.0263 (4)
H1'	0.0473	0.4182	0.4833	0.032*
C2'	0.10902 (18)	0.28480 (14)	0.48503 (15)	0.0231 (4)
H2'	0.1442	0.2879	0.5514	0.028*
C2	0.37116 (16)	0.09545 (13)	0.23153 (13)	0.0180 (4)
C3'	0.11662 (17)	0.20141 (13)	0.42843 (14)	0.0188 (4)
C3	0.35748 (17)	−0.04166 (13)	0.11768 (14)	0.0204 (4)
C4	0.33879 (19)	−0.07060 (14)	0.00610 (14)	0.0252 (4)
H40	0.3814	−0.1287	−0.0061	0.038*
H41	0.3706	−0.0225	−0.0386	0.038*
H42	0.2524	−0.0790	−0.0083	0.038*
C4'	0.05884 (17)	0.19924 (14)	0.33050 (14)	0.0216 (4)
H4'	0.0611	0.1442	0.2913	0.026*
C5	0.41102 (17)	0.13772 (12)	0.42180 (14)	0.0178 (4)
C5'	−0.00180 (17)	0.27755 (14)	0.29079 (15)	0.0234 (4)
H5'	−0.0408	0.2737	0.2260	0.028*
C6	0.31344 (17)	0.12846 (13)	0.50691 (13)	0.0185 (4)
H60	0.3370	0.0759	0.5512	0.022*
H61	0.3176	0.1848	0.5495	0.022*
C6'	−0.00551 (18)	0.36170 (14)	0.34573 (16)	0.0247 (4)
C7	0.17835 (17)	0.11399 (13)	0.47324 (14)	0.0191 (4)
H7	0.1752	0.0644	0.4203	0.023*
C7'	−0.0625 (2)	0.44905 (15)	0.29915 (17)	0.0326 (5)
H70'	−0.0004	0.4848	0.2644	0.049*
H71'	−0.0974	0.4866	0.3533	0.049*
H72'	−0.1260	0.4315	0.2500	0.049*
C8	0.10620 (18)	0.07994 (13)	0.56829 (14)	0.0227 (4)
H80	0.1403	0.0215	0.5928	0.034*
H81	0.0213	0.0708	0.5487	0.034*
H82	0.1120	0.1263	0.6226	0.034*
C9	0.53585 (18)	0.15303 (13)	0.47409 (14)	0.0200 (4)
C10	0.64558 (18)	0.16273 (13)	0.43130 (15)	0.0226 (4)
C11	0.67035 (19)	0.16274 (15)	0.31623 (16)	0.0286 (5)
H111	0.7302	0.1151	0.3009	0.043*
H112	0.7013	0.2233	0.2961	0.043*
H113	0.5953	0.1498	0.2784	0.043*
C12	0.75806 (19)	0.17719 (15)	0.49976 (17)	0.0304 (5)
H121	0.7982	0.2348	0.4807	0.046*
H122	0.8138	0.1254	0.4911	0.046*
H123	0.7339	0.1807	0.5712	0.046*
C41	0.37297 (17)	0.30457 (13)	0.37021 (13)	0.0177 (4)
C42	0.33714 (19)	0.37167 (13)	0.28539 (14)	0.0231 (4)
H420	0.3991	0.3715	0.2330	0.035*
H421	0.3296	0.4340	0.3137	0.035*
H422	0.2597	0.3527	0.2550	0.035*
N1	0.35903 (15)	0.05391 (11)	0.13421 (12)	0.0192 (3)
N3	0.35840 (14)	0.18471 (10)	0.24065 (11)	0.0183 (3)
N4	0.38013 (14)	0.21218 (10)	0.34384 (11)	0.0174 (3)
O1	0.36850 (13)	−0.09778 (9)	0.18908 (10)	0.0256 (3)
O2	0.39419 (12)	0.32905 (9)	0.46085 (9)	0.0213 (3)
S1	0.40785 (4)	0.02872 (3)	0.34223 (3)	0.01914 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1'	0.0305 (11)	0.0224 (10)	0.0261 (10)	0.0034 (8)	0.0050 (8)	−0.0035 (8)
C2'	0.0251 (10)	0.0248 (10)	0.0195 (9)	0.0012 (8)	0.0007 (8)	−0.0015 (8)
C2	0.0184 (9)	0.0205 (9)	0.0153 (9)	0.0010 (7)	0.0019 (7)	0.0011 (7)
C3'	0.0175 (9)	0.0199 (9)	0.0192 (9)	−0.0004 (7)	0.0020 (7)	0.0011 (7)
C3	0.0198 (9)	0.0198 (9)	0.0215 (10)	0.0000 (8)	0.0010 (7)	−0.0005 (7)
C4	0.0334 (11)	0.0220 (10)	0.0201 (10)	0.0008 (8)	−0.0041 (8)	−0.0041 (8)
C4'	0.0212 (10)	0.0228 (9)	0.0207 (9)	−0.0018 (8)	0.0007 (7)	−0.0010 (8)
C5	0.0221 (9)	0.0169 (9)	0.0144 (8)	0.0007 (7)	0.0003 (7)	0.0003 (7)
C5'	0.0206 (10)	0.0304 (10)	0.0192 (9)	−0.0002 (8)	0.0002 (8)	0.0043 (8)
C6	0.0239 (10)	0.0187 (9)	0.0128 (8)	0.0013 (8)	−0.0008 (7)	0.0012 (7)
C6'	0.0196 (10)	0.0272 (10)	0.0276 (10)	0.0032 (8)	0.0058 (8)	0.0068 (8)
C7	0.0231 (10)	0.0181 (9)	0.0160 (9)	−0.0001 (7)	0.0011 (7)	−0.0020 (7)
C7'	0.0328 (12)	0.0314 (11)	0.0338 (12)	0.0119 (9)	0.0082 (9)	0.0077 (9)
C8	0.0248 (10)	0.0216 (9)	0.0216 (10)	−0.0014 (8)	0.0009 (8)	0.0000 (8)
C9	0.0245 (10)	0.0197 (9)	0.0157 (9)	0.0011 (7)	−0.0032 (7)	0.0018 (7)
C10	0.0253 (10)	0.0171 (9)	0.0254 (10)	0.0020 (8)	−0.0015 (8)	0.0013 (7)
C11	0.0258 (11)	0.0285 (11)	0.0316 (11)	−0.0001 (9)	0.0064 (9)	−0.0002 (9)
C12	0.0229 (11)	0.0271 (11)	0.0410 (12)	0.0019 (9)	−0.0029 (9)	−0.0013 (9)
C41	0.0193 (9)	0.0187 (9)	0.0153 (9)	−0.0014 (7)	0.0009 (7)	−0.0003 (7)
C42	0.0332 (11)	0.0183 (9)	0.0176 (9)	0.0004 (8)	−0.0029 (8)	−0.0003 (7)
N1	0.0274 (9)	0.0185 (8)	0.0117 (7)	0.0001 (7)	0.0000 (6)	−0.0010 (6)
N3	0.0230 (8)	0.0188 (8)	0.0130 (7)	0.0003 (6)	−0.0009 (6)	−0.0019 (6)
N4	0.0240 (8)	0.0174 (7)	0.0107 (7)	0.0021 (6)	−0.0006 (6)	0.0014 (6)
O1	0.0358 (8)	0.0201 (7)	0.0208 (7)	0.0013 (6)	0.0010 (6)	0.0016 (6)
O2	0.0277 (7)	0.0211 (7)	0.0149 (6)	0.0000 (6)	−0.0011 (5)	−0.0019 (5)
S1	0.0254 (2)	0.0175 (2)	0.0145 (2)	0.00277 (19)	0.00084 (17)	0.00137 (18)

Geometric parameters (Å, º) top

C1'—C2'	1.384 (3)	C6'—C7'	1.505 (3)
C1'—C6'	1.392 (3)	C7—C8	1.540 (3)
C1'—H1'	0.93	C7—H7	0.98
C2'—C3'	1.392 (3)	C7'—H70'	0.96
C2'—H2'	0.93	C7'—H71'	0.96
C2—N3	1.280 (2)	C7'—H72'	0.96
C2—N1	1.387 (2)	C8—H80	0.96
C2—S1	1.7497 (18)	C8—H81	0.96
C3'—C4'	1.397 (3)	C8—H82	0.96
C3'—C7	1.519 (2)	C9—C10	1.327 (3)
C3—O1	1.219 (2)	C9—H9	0.97 (2)
C3—N1	1.373 (2)	C10—C12	1.507 (3)
C3—C4	1.502 (3)	C10—C11	1.508 (3)
C4—H40	0.96	C11—H111	0.96
C4—H41	0.96	C11—H112	0.96
C4—H42	0.96	C11—H113	0.96
C4'—C5'	1.385 (3)	C12—H121	0.96
C4'—H4'	0.93	C12—H122	0.96
C5—N4	1.491 (2)	C12—H123	0.96
C5—C9	1.518 (3)	C41—O2	1.234 (2)
C5—C6	1.541 (2)	C41—N4	1.357 (2)
C5—S1	1.8545 (18)	C41—C42	1.494 (2)
C5'—C6'	1.388 (3)	C42—H420	0.96
C5'—H5'	0.93	C42—H421	0.96
C6—C7	1.536 (3)	C42—H422	0.96
C6—H60	0.97	N1—H2	0.87 (2)
C6—H61	0.97	N3—N4	1.399 (2)

C2'—C1'—C6'	121.60 (18)	C6'—C7'—H70'	109.5
C2'—C1'—H1'	119.2	C6'—C7'—H71'	109.5
C6'—C1'—H1'	119.2	H70'—C7'—H71'	109.5
C1'—C2'—C3'	121.06 (18)	C6'—C7'—H72'	109.5
C1'—C2'—H2'	119.5	H70'—C7'—H72'	109.5
C3'—C2'—H2'	119.5	H71'—C7'—H72'	109.5
N3—C2—N1	119.63 (16)	C7—C8—H80	109.5
N3—C2—S1	119.00 (14)	C7—C8—H81	109.5
N1—C2—S1	121.35 (14)	H80—C8—H81	109.5
C2'—C3'—C4'	117.38 (17)	C7—C8—H82	109.5
C2'—C3'—C7	121.72 (16)	H80—C8—H82	109.5
C4'—C3'—C7	120.80 (16)	H81—C8—H82	109.5
O1—C3—N1	121.87 (17)	C10—C9—C5	129.19 (17)
O1—C3—C4	123.36 (17)	C10—C9—H9	117.4 (12)
N1—C3—C4	114.76 (16)	C5—C9—H9	113.5 (12)
C3—C4—H40	109.5	C9—C10—C12	119.73 (18)
C3—C4—H41	109.5	C9—C10—C11	125.62 (18)
H40—C4—H41	109.5	C12—C10—C11	114.63 (17)
C3—C4—H42	109.5	C10—C11—H111	109.5
H40—C4—H42	109.5	C10—C11—H112	109.5
H41—C4—H42	109.5	H111—C11—H112	109.5
C5'—C4'—C3'	121.18 (18)	C10—C11—H113	109.5
C5'—C4'—H4'	119.4	H111—C11—H113	109.5
C3'—C4'—H4'	119.4	H112—C11—H113	109.5
N4—C5—C9	112.66 (15)	C10—C12—H121	109.5
N4—C5—C6	112.84 (14)	C10—C12—H122	109.5
C9—C5—C6	108.48 (15)	H121—C12—H122	109.5
N4—C5—S1	102.63 (11)	C10—C12—H123	109.5
C9—C5—S1	111.83 (13)	H121—C12—H123	109.5
C6—C5—S1	108.29 (12)	H122—C12—H123	109.5
C4'—C5'—C6'	121.37 (18)	O2—C41—N4	119.83 (16)
C4'—C5'—H5'	119.3	O2—C41—C42	123.49 (16)
C6'—C5'—H5'	119.3	N4—C41—C42	116.67 (15)
C7—C6—C5	118.41 (15)	C41—C42—H420	109.5
C7—C6—H60	107.7	C41—C42—H421	109.5
C5—C6—H60	107.7	H420—C42—H421	109.5
C7—C6—H61	107.7	C41—C42—H422	109.5
C5—C6—H61	107.7	H420—C42—H422	109.5
H60—C6—H61	107.1	H421—C42—H422	109.5
C5'—C6'—C1'	117.35 (18)	C3—N1—C2	124.06 (16)
C5'—C6'—C7'	121.43 (18)	C3—N1—H2	119.1 (16)
C1'—C6'—C7'	121.17 (19)	C2—N1—H2	116.7 (16)
C3'—C7—C6	114.25 (15)	C2—N3—N4	110.24 (14)
C3'—C7—C8	109.29 (15)	C41—N4—N3	119.79 (14)
C6—C7—C8	108.32 (15)	C41—N4—C5	122.03 (14)
C3'—C7—H7	108.3	N3—N4—C5	118.18 (14)
C6—C7—H7	108.3	C2—S1—C5	89.94 (8)
C8—C7—H7	108.3

C6'—C1'—C2'—C3'	0.9 (3)	O1—C3—N1—C2	−1.0 (3)
C1'—C2'—C3'—C4'	−2.1 (3)	C4—C3—N1—C2	177.88 (17)
C1'—C2'—C3'—C7	−178.47 (17)	N3—C2—N1—C3	−172.52 (18)
C2'—C3'—C4'—C5'	1.0 (3)	S1—C2—N1—C3	9.3 (3)
C7—C3'—C4'—C5'	177.45 (17)	N1—C2—N3—N4	−177.12 (15)
C3'—C4'—C5'—C6'	1.3 (3)	S1—C2—N3—N4	1.1 (2)
N4—C5—C6—C7	53.5 (2)	O2—C41—N4—N3	−178.76 (15)
C9—C5—C6—C7	179.04 (15)	C42—C41—N4—N3	2.1 (2)
S1—C5—C6—C7	−59.41 (18)	O2—C41—N4—C5	1.1 (3)
C4'—C5'—C6'—C1'	−2.5 (3)	C42—C41—N4—C5	−178.05 (16)
C4'—C5'—C6'—C7'	175.03 (18)	C2—N3—N4—C41	179.12 (16)
C2'—C1'—C6'—C5'	1.4 (3)	C2—N3—N4—C5	−0.7 (2)
C2'—C1'—C6'—C7'	−176.10 (19)	C9—C5—N4—C41	−59.4 (2)
C2'—C3'—C7—C6	−57.9 (2)	C6—C5—N4—C41	63.9 (2)
C4'—C3'—C7—C6	125.84 (18)	S1—C5—N4—C41	−179.78 (14)
C2'—C3'—C7—C8	63.6 (2)	C9—C5—N4—N3	120.51 (17)
C4'—C3'—C7—C8	−112.64 (19)	C6—C5—N4—N3	−116.23 (16)
C5—C6—C7—C3'	−73.3 (2)	S1—C5—N4—N3	0.08 (18)
C5—C6—C7—C8	164.63 (15)	N3—C2—S1—C5	−0.96 (16)
N4—C5—C9—C10	−55.8 (3)	N1—C2—S1—C5	177.27 (16)
C6—C5—C9—C10	178.55 (19)	N4—C5—S1—C2	0.41 (12)
S1—C5—C9—C10	59.2 (2)	C9—C5—S1—C2	−120.59 (14)
C5—C9—C10—C12	−179.85 (17)	C6—C5—S1—C2	119.95 (13)
C5—C9—C10—C11	1.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2···O2ⁱ	0.87 (2)	1.96 (2)	2.811 (2)	167 (2)

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₇N₃O₂S
M_r	373.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.855 (2), 14.193 (2), 12.854 (4)
β (°)	90.955 (11)
V (Å³)	1980.1 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.28 × 0.17 × 0.12

Data collection
Diffractometer	Bruker X8 APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7884, 4030, 3365
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.094, 1.10
No. of reflections	4030
No. of parameters	249
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.20

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2005), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2···O2ⁱ	0.87 (2)	1.96 (2)	2.811 (2)	167 (2)

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

The authors thank Professor J. C. Daran for fruitful discussions.

References

Beatriz, N. B., Albertina, G. M., Miriam, M. A., Angel, A. L., Graciela, Y. M. & Norma, B. D. (2002). Arkivoc, x, 14–23. Google Scholar
Bruker (2005). APEX2 and SAINT-Plus. Bruker AXS Inc.,Madison, Wisconsin, USA. Google Scholar
Demirbas, N., Demirbas, A., Karaoglu, S. A. & Çelik, E. (2005). Arkivoc, i, 75–91. CrossRef Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Holla, B. S., Poorjary, N. K., Rao, S. B. & Shivananda, M. K. (2002). Eur. J. Med. Chem. 37, 511–517. Web of Science PubMed Google Scholar
Kritsanida, M., Mouroutsou, A., Marakos, P., Pouli, N., Papakonstantinou-Garoufalias, S., Pannecouque, C., Witvrouw, M. & Clercq, E. D. (2002). Farmaco, 57, 253–257. Web of Science CrossRef PubMed CAS Google Scholar
Loughzail, M., Mazoir, N., Maya, C. M., Berraho, M., Benharref, A. & Bouhmaida, N. (2009). Acta Cryst. E65, o4. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nizamuddin, G. M., Khan, M. H. & Srivastava, M. K. (1999). J. Sci. Ind. Res. 58, 538–542. CAS Google Scholar
Sakthivel, P., Joseph, P. S., Muthiah, P. T., Sethusankar, K. & Thennarasu, S. (2008). Acta Cryst. E64, o216. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, X.-W., Zhang, Y., Zhang, Z.-Y., Wang, Q. & Wang, S.-F. (1999). Indian J. Chem. Sect. B, 38, 380–382. Google Scholar
Tebaa, M., Mazoir, N., Maya, C. M., Nouzha, B., Benharref, A. & Berraho, M. (2009). Acta Cryst. E65, o267–o268. Web of Science CSD CrossRef IUCr Journals Google Scholar
Udupi, R. H., Suresh, G. V., Sety, S. R. & Bhat, A. R. (2000). J. Indian Chem. Soc. 77, 302–304. CAS Google Scholar

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Volume 65| Part 6| June 2009| Pages o1269-o1270

doi:10.1107/S1600536809017127

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

N-[4-Acetyl-5-(2-methylprop-1-enyl)-5-(2-p-tolyl­prop­yl)-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-(2-methylprop-1-enyl)-5-(2-p-tolylpropyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide