N-[4-Acetyl-5-(2-methylprop-1-enyl)-5-(2-p-tolyl-prop-yl)-4,5-dihydro-1,3,4-thia-diazol-2-yl]acetamide.

The title heterocyclic compound, C(20)H(27)N(3)O(2)S, was synthesized from 2-(4-methyl-cyclo-hex-3-en-yl)-6-methyl-hepta-2,5-dien-4-one, which was isolated from the essential oil Cedrus atlantica. The thia-diazole 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 thia-diazole ring and the acetamide plane is 7.62 (10)°. In the crystal, mol-ecules are linked into chains running along the c axis by inter-molecular 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 = 373.51

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.094

S = 1.10

4030 reflections

249 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.20 e Å−3

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 ▶).

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

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

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

C20H27N3O2S	F(000) = 800
Mr = 373.51	Dx = 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

Bruker X8 APEX CCD area-detector diffractometer	3365 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
graphite	θmax = 26.4°, θmin = 2.8°
φ and ω scans	h = 0→13
7884 measured reflections	k = −17→17
4030 independent reflections	l = −16→16

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(Fo2) + (0.0257P)2 + 1.5568P] where P = (Fo2 + 2Fc2)/3
4030 reflections	(Δ/σ)max = 0.001
249 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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)

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) .