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

The title heterocyclic compound, C(17)H(23)N(3)O(2)S, was synthesized from 4-(4-methyl-cyclo-hex-3-en-yl)pent-3-en-2-one, which was isolated from Cedrus atlantica essential oil. The thia-diazole ring adopts a flattened envelope conformation, with the flap sp(3)-hybridized C atom lying 0.259 (1) Å out of the plane of the other four atoms. The screw-related mol-ecules are linked into chains along the b axis by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For 1,3,4-thia­diazole derivatives and their biological activity, see: Beatriz et al. (2002 ▶); Loughzail et al. (2009 ▶); Mazoir et al. (2008 ▶); Mohammed et al. (2008 ▶); Nakagawa et al. (1996 ▶); Sakthivel et al. (2008 ▶); Tehranchian et al. (2005 ▶); Wang et al. (1999 ▶, 2004 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C17H23N3O2S

M = 333.44

Monoclinic,

a = 9.3984 (2) Å

b = 11.0510 (2) Å

c = 16.6045 (3) Å

β = 90.442 (10)°

V = 1724.52 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 298 (2) K

0.5 × 0.4 × 0.3 mm

Data collection

Bruker X8 APEX CCD area-detector diffractometer

Absorption correction: none

52162 measured reflections

8286 independent reflections

7182 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.108

S = 1.03

8286 reflections

221 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −0.19 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: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia,1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000191/ci2746sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000191/ci2746Isup2.hkl

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

C17H23N3O2S	F(000) = 712
Mr = 333.44	Dx = 1.284 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 31976 reflections
a = 9.3984 (2) Å	θ = 2.2–36.5°
b = 11.0510 (2) Å	µ = 0.20 mm−1
c = 16.6045 (3) Å	T = 298 K
β = 90.442 (10)°	Prism, colourless
V = 1724.52 (6) Å3	0.5 × 0.4 × 0.3 mm
Z = 4

Bruker X8 APEX CCD area-detector diffractometer	7182 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
graphite	θmax = 36.8°, θmin = 2.2°
φ and ω scans	h = −14→15
52162 measured reflections	k = −18→17
8286 independent reflections	l = −27→27

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0594P)2 + 0.2773P] where P = (Fo2 + 2Fc2)/3
8286 reflections	(Δ/σ)max = 0.002
221 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

	x	y	z	Uiso*/Ueq
C1'	−0.18648 (9)	0.69929 (8)	0.22865 (5)	0.03405 (16)
H1'	−0.2631	0.7423	0.2493	0.041*
C2'	−0.12028 (8)	0.74007 (7)	0.15872 (5)	0.02883 (13)
H2'	−0.1553	0.8087	0.1329	0.035*
C2	0.40705 (7)	0.72005 (6)	0.13520 (4)	0.02074 (10)
C3'	−0.00246 (7)	0.68003 (6)	0.12659 (4)	0.02299 (11)
C3	0.58917 (7)	0.58558 (7)	0.08145 (4)	0.02531 (12)
C4	0.67040 (8)	0.47195 (8)	0.09881 (5)	0.03082 (14)
H40	0.6397	0.4094	0.0625	0.046*
H41	0.6534	0.4471	0.1533	0.046*
H42	0.7702	0.4865	0.0917	0.046*
C4'	0.04426 (8)	0.57608 (7)	0.16569 (5)	0.02818 (13)
H4'	0.1221	0.5340	0.1458	0.034*
C5	0.24444 (7)	0.89236 (6)	0.09425 (4)	0.02261 (11)
C5'	−0.02462 (10)	0.53384 (8)	0.23496 (5)	0.03469 (17)
H5'	0.0073	0.4631	0.2595	0.042*
C6	0.10835 (8)	0.85717 (6)	0.04946 (4)	0.02444 (12)
H61	0.1172	0.8834	−0.0060	0.029*
H62	0.0302	0.9021	0.0728	0.029*
C6'	−0.13955 (10)	0.59549 (9)	0.26777 (5)	0.03553 (17)
C7'	−0.21196 (14)	0.55330 (13)	0.34392 (6)	0.0557 (3)
H70'	−0.1661	0.4813	0.3634	0.083*
H71'	−0.3103	0.5363	0.3325	0.083*
H72'	−0.2054	0.6155	0.3841	0.083*
C7	0.06784 (7)	0.72237 (6)	0.04914 (4)	0.02407 (11)
C8	−0.02971 (10)	0.69513 (9)	−0.02232 (5)	0.03593 (17)
H80	0.0164	0.7187	−0.0713	0.054*
H81	−0.1169	0.7395	−0.0168	0.054*
H82	−0.0501	0.6100	−0.0239	0.054*
C9	0.27064 (10)	1.02844 (7)	0.08864 (5)	0.03188 (15)
H90	0.3533	1.0493	0.1200	0.048*
H91	0.1895	1.0711	0.1090	0.048*
H92	0.2855	1.0505	0.0334	0.048*
C41	0.15568 (7)	0.88983 (6)	0.23768 (4)	0.02220 (11)
C42	0.16402 (9)	0.82781 (7)	0.31792 (4)	0.02797 (13)
H420	0.1094	0.7544	0.3161	0.042*
H421	0.1265	0.8802	0.3587	0.042*
H422	0.2615	0.8091	0.3304	0.042*
N1	0.49426 (6)	0.61997 (5)	0.14026 (3)	0.02274 (10)
N3	0.32596 (6)	0.74595 (5)	0.19539 (3)	0.02162 (10)
N4	0.24397 (6)	0.84788 (5)	0.17882 (3)	0.02167 (10)
O1	0.60479 (7)	0.64374 (7)	0.01970 (4)	0.03731 (14)
O2	0.07229 (6)	0.97409 (5)	0.22442 (3)	0.02734 (10)
S1	0.400452 (18)	0.813333 (16)	0.050251 (10)	0.02473 (5)
H4	0.4838 (13)	0.5774 (12)	0.1853 (8)	0.036 (3)*
H7	0.1540 (12)	0.6750 (10)	0.0411 (7)	0.028 (3)*

	U11	U22	U33	U12	U13	U23
C1'	0.0346 (4)	0.0368 (4)	0.0309 (3)	−0.0069 (3)	0.0063 (3)	−0.0080 (3)
C2'	0.0302 (3)	0.0267 (3)	0.0297 (3)	0.0019 (2)	0.0030 (2)	−0.0024 (2)
C2	0.0225 (2)	0.0212 (2)	0.0185 (2)	−0.00085 (19)	−0.00014 (18)	0.00030 (19)
C3'	0.0255 (3)	0.0214 (3)	0.0220 (3)	0.0002 (2)	−0.0027 (2)	−0.00210 (19)
C3	0.0203 (2)	0.0334 (3)	0.0222 (3)	0.0008 (2)	0.00024 (19)	−0.0032 (2)
C4	0.0255 (3)	0.0331 (3)	0.0338 (3)	0.0052 (2)	−0.0005 (2)	−0.0081 (3)
C4'	0.0296 (3)	0.0246 (3)	0.0303 (3)	−0.0003 (2)	−0.0072 (2)	0.0011 (2)
C5	0.0293 (3)	0.0197 (2)	0.0188 (2)	0.0009 (2)	−0.0005 (2)	0.00177 (19)
C5'	0.0396 (4)	0.0325 (4)	0.0318 (3)	−0.0098 (3)	−0.0116 (3)	0.0077 (3)
C6	0.0289 (3)	0.0245 (3)	0.0199 (2)	0.0025 (2)	−0.0023 (2)	0.0024 (2)
C6'	0.0407 (4)	0.0420 (4)	0.0238 (3)	−0.0185 (3)	−0.0029 (3)	−0.0004 (3)
C7'	0.0633 (7)	0.0724 (8)	0.0313 (4)	−0.0341 (6)	0.0034 (4)	0.0054 (5)
C7	0.0264 (3)	0.0251 (3)	0.0207 (2)	0.0018 (2)	−0.0016 (2)	−0.0032 (2)
C8	0.0402 (4)	0.0437 (4)	0.0238 (3)	−0.0051 (3)	−0.0066 (3)	−0.0053 (3)
C9	0.0445 (4)	0.0202 (3)	0.0310 (3)	−0.0016 (3)	−0.0006 (3)	0.0036 (2)
C41	0.0276 (3)	0.0205 (2)	0.0185 (2)	0.0008 (2)	−0.00094 (19)	−0.00301 (19)
C42	0.0367 (3)	0.0281 (3)	0.0191 (3)	0.0049 (3)	0.0014 (2)	0.0006 (2)
N1	0.0240 (2)	0.0233 (2)	0.0209 (2)	0.00241 (18)	0.00268 (17)	0.00121 (18)
N3	0.0262 (2)	0.0202 (2)	0.0184 (2)	0.00288 (18)	0.00029 (17)	0.00064 (17)
N4	0.0281 (2)	0.0199 (2)	0.0171 (2)	0.00304 (18)	−0.00031 (17)	0.00020 (16)
O1	0.0321 (3)	0.0550 (4)	0.0249 (2)	0.0069 (3)	0.0068 (2)	0.0066 (2)
O2	0.0344 (3)	0.0233 (2)	0.0244 (2)	0.00714 (18)	−0.00082 (18)	−0.00255 (17)
S1	0.02737 (8)	0.02713 (9)	0.01972 (8)	0.00035 (5)	0.00253 (5)	0.00433 (5)

C1'—C6'	1.3886 (14)	C6—C7	1.5375 (10)
C1'—C2'	1.3963 (12)	C6—H61	0.97
C1'—H1'	0.93	C6—H62	0.97
C2'—C3'	1.4001 (10)	C6'—C7'	1.5142 (13)
C2'—H2'	0.93	C7'—H70'	0.96
C2—N3	1.2936 (8)	C7'—H71'	0.96
C2—N1	1.3788 (9)	C7'—H72'	0.96
C2—S1	1.7478 (6)	C7—C8	1.5240 (10)
C3'—C4'	1.3891 (10)	C7—H7	0.974 (11)
C3'—C7	1.5239 (10)	C8—H80	0.96
C3—O1	1.2199 (9)	C8—H81	0.96
C3—N1	1.3810 (9)	C8—H82	0.96
C3—C4	1.4966 (11)	C9—H90	0.96
C4—H40	0.96	C9—H91	0.96
C4—H41	0.96	C9—H92	0.96
C4—H42	0.96	C41—O2	1.2357 (8)
C4'—C5'	1.4040 (12)	C41—N4	1.3679 (8)
C4'—H4'	0.93	C41—C42	1.4998 (10)
C5—N4	1.4878 (8)	C42—H420	0.96
C5—C6	1.5250 (10)	C42—H421	0.96
C5—C9	1.5267 (10)	C42—H422	0.96
C5—S1	1.8609 (7)	N1—H4	0.889 (13)
C5'—C6'	1.3916 (14)	N3—N4	1.3911 (8)
C5'—H5'	0.93
C6'—C1'—C2'	120.90 (8)	C6'—C7'—H70'	109.5
C6'—C1'—H1'	119.5	C6'—C7'—H71'	109.5
C2'—C1'—H1'	119.5	H70'—C7'—H71'	109.5
C1'—C2'—C3'	121.52 (7)	C6'—C7'—H72'	109.5
C1'—C2'—H2'	119.2	H70'—C7'—H72'	109.5
C3'—C2'—H2'	119.2	H71'—C7'—H72'	109.5
N3—C2—N1	118.94 (6)	C3'—C7—C8	109.53 (6)
N3—C2—S1	118.40 (5)	C3'—C7—C6	113.80 (5)
N1—C2—S1	122.66 (5)	C8—C7—C6	109.97 (6)
C4'—C3'—C2'	117.51 (7)	C3'—C7—H7	108.5 (7)
C4'—C3'—C7	120.72 (6)	C8—C7—H7	106.4 (7)
C2'—C3'—C7	121.70 (6)	C6—C7—H7	108.3 (7)
O1—C3—N1	122.14 (7)	C7—C8—H80	109.5
O1—C3—C4	122.65 (7)	C7—C8—H81	109.5
N1—C3—C4	115.21 (6)	H80—C8—H81	109.5
C3—C4—H40	109.5	C7—C8—H82	109.5
C3—C4—H41	109.5	H80—C8—H82	109.5
H40—C4—H41	109.5	H81—C8—H82	109.5
C3—C4—H42	109.5	C5—C9—H90	109.5
H40—C4—H42	109.5	C5—C9—H91	109.5
H41—C4—H42	109.5	H90—C9—H91	109.5
C3'—C4'—C5'	120.78 (8)	C5—C9—H92	109.5
C3'—C4'—H4'	119.6	H90—C9—H92	109.5
C5'—C4'—H4'	119.6	H91—C9—H92	109.5
N4—C5—C6	111.56 (5)	O2—C41—N4	121.03 (6)
N4—C5—C9	112.62 (6)	O2—C41—C42	122.10 (6)
C6—C5—C9	110.89 (6)	N4—C41—C42	116.87 (6)
N4—C5—S1	102.92 (4)	C41—C42—H420	109.5
C6—C5—S1	110.44 (5)	C41—C42—H421	109.5
C9—C5—S1	108.08 (5)	H420—C42—H421	109.5
C6'—C5'—C4'	121.47 (8)	C41—C42—H422	109.5
C6'—C5'—H5'	119.3	H420—C42—H422	109.5
C4'—C5'—H5'	119.3	H421—C42—H422	109.5
C5—C6—C7	117.10 (5)	C2—N1—C3	124.37 (6)
C5—C6—H61	108.0	C2—N1—H4	113.9 (8)
C7—C6—H61	108.0	C3—N1—H4	121.7 (8)
C5—C6—H62	108.0	C2—N3—N4	110.79 (5)
C7—C6—H62	108.0	C41—N4—N3	118.12 (5)
H61—C6—H62	107.3	C41—N4—C5	124.65 (5)
C1'—C6'—C5'	117.78 (7)	N3—N4—C5	116.65 (5)
C1'—C6'—C7'	120.12 (10)	C2—S1—C5	89.03 (3)
C5'—C6'—C7'	122.10 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H4···O2i	0.89 (1)	1.96 (1)	2.8391 (7)	169 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H4⋯O2i	0.89 (1)	1.96 (1)	2.8391 (7)	169 (1)

Symmetry code: (i) .