N-[4-Acetyl-5-(4-fluoro-phen-yl)-4,5-di-hydro-1,3,4-thia-diazol-2-yl]acetamide.

The title mol-ecule, C12H12FN3O2S, shows a short intra-molecular S⋯O contact of 2.682 (18) Å. The dihedral angle between the thia-diazole ring and the benzene ring is 86.82 (11)°. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds generate an R 2 (1)(6) graph-set motif between adjacent mol-ecules. Pairs of futher C-H⋯O hydrogen bonds form inversion dimers with R 2 (2)(8) ring motifs. These combine to generate a three-dimensional network and stack the mol-ecules along the b axis.

Related literature

For biological applications of 1,3,4-thia­diazole derivatives, see: Matysiak & Opolski (2006 ▶); Kumar et al. (2012 ▶); Oruç et al. (2004 ▶); Kadi et al. (2007 ▶); Noolvi et al. (2011 ▶); Matysiak et al. (2006 ▶); Marganakop et al. (2012 ▶). For a related structure, see: Zhang (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C12H12FN3O2S

M = 281.31

Monoclinic,

a = 9.5061 (6) Å

b = 11.2152 (7) Å

c = 12.7752 (7) Å

β = 101.823 (4)°

V = 1333.11 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.770, T max = 1.000

11372 measured reflections

2352 independent reflections

2035 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.121

S = 1.07

2352 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.34 e Å−3

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: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813009367/sj5314sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009367/sj5314Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009367/sj5314Isup3.cml

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

C12H12FN3O2S	F(000) = 584
Mr = 281.31	Dx = 1.402 Mg m−3
Monoclinic, P21/c	Melting point: 490 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.5061 (6) Å	Cell parameters from 2352 reflections
b = 11.2152 (7) Å	θ = 2.2–25.0°
c = 12.7752 (7) Å	µ = 0.26 mm−1
β = 101.823 (4)°	T = 296 K
V = 1333.11 (14) Å3	Plate, colourless
Z = 4	0.24 × 0.20 × 0.12 mm

Bruker SMART CCD area-detector diffractometer	2352 independent reflections
Radiation source: fine-focus sealed tube	2035 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω and φ scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −11→11
Tmin = 0.770, Tmax = 1.000	k = −13→12
11372 measured reflections	l = −15→15

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0619P)2 + 0.7142P] where P = (Fo2 + 2Fc2)/3
2352 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Experimental. Spectroscopic data IR (KBr); 3233, 2799, 1646, 1626, 1H NMR (300 MHz, CDCl3, δ p.p.m.): 2.11 (s, 3H, CH3 of NHCOCH3), 2.24 (s, 3H, CH3 of –NCOCH3), 4.70 (s, 1H, C—H of C5—H), 6.85–7.10 (m, 4H, Ar—H), 11.77 (s, 1H, NHCO), MS (m/z, 70 eV); 282 (M+1, 20), 239 (26), 204 (100).

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
F1	−0.11204 (19)	0.1673 (2)	0.41894 (18)	0.1026 (7)
S2	0.32591 (7)	0.09255 (5)	0.09191 (4)	0.0449 (2)
O3	0.2686 (2)	−0.01822 (15)	−0.09810 (14)	0.0665 (5)
O4	0.56411 (17)	0.11842 (14)	0.42490 (13)	0.0472 (4)
N5	0.3591 (2)	−0.14036 (15)	0.03899 (13)	0.0407 (4)
H5	0.3826	−0.2127	0.0571	0.049*
N6	0.45429 (18)	−0.08120 (15)	0.21164 (13)	0.0367 (4)
N7	0.46451 (18)	0.01994 (15)	0.27693 (14)	0.0374 (4)
C8	0.0057 (3)	0.1564 (3)	0.3747 (2)	0.0626 (7)
C9	0.0942 (3)	0.2522 (2)	0.3768 (2)	0.0558 (6)
H9	0.0750	0.3239	0.4076	0.067*
C10	0.2141 (2)	0.2394 (2)	0.33124 (17)	0.0441 (5)
H10	0.2768	0.3032	0.3321	0.053*
C11	0.2413 (2)	0.13353 (19)	0.28503 (16)	0.0372 (5)
C12	0.1473 (3)	0.0389 (2)	0.2839 (2)	0.0551 (6)
H12	0.1645	−0.0327	0.2520	0.066*
C13	0.0287 (3)	0.0497 (3)	0.3296 (3)	0.0677 (8)
H13	−0.0340	−0.0140	0.3297	0.081*
C14	0.3719 (2)	0.12171 (18)	0.23621 (16)	0.0375 (5)
H14	0.4283	0.1953	0.2490	0.045*
C15	0.3864 (2)	−0.05435 (18)	0.11717 (16)	0.0358 (5)
C16	0.2973 (3)	−0.1186 (2)	−0.06565 (17)	0.0453 (5)
C17	0.2681 (3)	−0.2264 (2)	−0.1344 (2)	0.0604 (7)
H17A	0.2994	−0.2961	−0.0925	0.091*
H17B	0.3192	−0.2206	−0.1917	0.091*
H17C	0.1669	−0.2321	−0.1635	0.091*
C18	0.5596 (2)	0.02706 (18)	0.37069 (16)	0.0363 (5)
C19	0.6546 (3)	−0.0775 (2)	0.40480 (18)	0.0478 (6)
H19A	0.6340	−0.1389	0.3515	0.072*
H19B	0.6377	−0.1074	0.4716	0.072*
H19C	0.7533	−0.0536	0.4134	0.072*

	U11	U22	U33	U12	U13	U23
F1	0.0620 (10)	0.1312 (19)	0.1269 (17)	0.0023 (11)	0.0478 (11)	−0.0189 (15)
S2	0.0679 (4)	0.0285 (3)	0.0365 (3)	0.0074 (2)	0.0066 (3)	0.0035 (2)
O3	0.1095 (15)	0.0395 (10)	0.0444 (9)	0.0104 (10)	0.0014 (9)	0.0058 (8)
O4	0.0573 (9)	0.0333 (8)	0.0485 (9)	−0.0053 (7)	0.0049 (7)	−0.0088 (7)
N5	0.0608 (11)	0.0261 (9)	0.0339 (9)	0.0035 (8)	0.0064 (8)	0.0009 (7)
N6	0.0464 (10)	0.0272 (9)	0.0352 (9)	0.0023 (7)	0.0055 (7)	−0.0024 (7)
N7	0.0465 (10)	0.0263 (9)	0.0373 (9)	0.0032 (7)	0.0038 (7)	−0.0032 (7)
C8	0.0439 (13)	0.082 (2)	0.0635 (16)	0.0081 (13)	0.0142 (12)	−0.0031 (15)
C9	0.0545 (14)	0.0586 (16)	0.0519 (14)	0.0122 (12)	0.0057 (11)	−0.0124 (12)
C10	0.0479 (12)	0.0374 (12)	0.0440 (12)	0.0021 (9)	0.0022 (9)	−0.0049 (10)
C11	0.0425 (11)	0.0306 (11)	0.0355 (10)	0.0022 (9)	0.0007 (8)	0.0009 (8)
C12	0.0569 (14)	0.0389 (13)	0.0706 (17)	−0.0043 (11)	0.0157 (12)	−0.0055 (12)
C13	0.0537 (15)	0.0634 (18)	0.089 (2)	−0.0146 (13)	0.0225 (14)	−0.0058 (16)
C14	0.0481 (11)	0.0247 (10)	0.0381 (11)	0.0007 (9)	0.0051 (9)	0.0005 (8)
C15	0.0451 (11)	0.0272 (10)	0.0352 (11)	0.0004 (9)	0.0083 (9)	0.0008 (8)
C16	0.0603 (14)	0.0361 (12)	0.0377 (11)	0.0047 (10)	0.0060 (10)	0.0030 (10)
C17	0.0867 (18)	0.0469 (15)	0.0405 (13)	0.0070 (13)	−0.0036 (12)	−0.0061 (11)
C18	0.0389 (10)	0.0315 (11)	0.0387 (11)	−0.0051 (8)	0.0082 (8)	−0.0007 (9)
C19	0.0494 (13)	0.0440 (14)	0.0452 (13)	0.0053 (10)	−0.0014 (10)	−0.0028 (10)

F1—C8	1.359 (3)	C10—C11	1.374 (3)
S2—C15	1.753 (2)	C10—H10	0.9300
S2—C14	1.835 (2)	C11—C12	1.386 (3)
O3—C16	1.211 (3)	C11—C14	1.505 (3)
O4—C18	1.233 (3)	C12—C13	1.376 (4)
N5—C16	1.368 (3)	C12—H12	0.9300
N5—C15	1.374 (3)	C13—H13	0.9300
N5—H5	0.8600	C14—H14	0.9800
N6—C15	1.283 (3)	C16—C17	1.487 (3)
N6—N7	1.399 (2)	C17—H17A	0.9600
N7—C18	1.347 (3)	C17—H17B	0.9600
N7—C14	1.470 (3)	C17—H17C	0.9600
C8—C9	1.361 (4)	C18—C19	1.490 (3)
C8—C13	1.365 (4)	C19—H19A	0.9600
C9—C10	1.389 (3)	C19—H19B	0.9600
C9—H9	0.9300	C19—H19C	0.9600
C15—S2—C14	88.91 (9)	N7—C14—S2	102.66 (13)
C16—N5—C15	124.35 (18)	C11—C14—S2	112.67 (14)
C16—N5—H5	117.8	N7—C14—H14	109.1
C15—N5—H5	117.8	C11—C14—H14	109.1
C15—N6—N7	109.31 (17)	S2—C14—H14	109.1
C18—N7—N6	122.01 (17)	N6—C15—N5	120.17 (19)
C18—N7—C14	120.85 (17)	N6—C15—S2	118.48 (16)
N6—N7—C14	117.06 (16)	N5—C15—S2	121.34 (15)
F1—C8—C9	118.6 (3)	O3—C16—N5	121.5 (2)
F1—C8—C13	118.1 (3)	O3—C16—C17	123.5 (2)
C9—C8—C13	123.3 (2)	N5—C16—C17	115.0 (2)
C8—C9—C10	117.8 (2)	C16—C17—H17A	109.5
C8—C9—H9	121.1	C16—C17—H17B	109.5
C10—C9—H9	121.1	H17A—C17—H17B	109.5
C11—C10—C9	120.8 (2)	C16—C17—H17C	109.5
C11—C10—H10	119.6	H17A—C17—H17C	109.5
C9—C10—H10	119.6	H17B—C17—H17C	109.5
C10—C11—C12	119.2 (2)	O4—C18—N7	119.26 (19)
C10—C11—C14	119.87 (19)	O4—C18—C19	122.74 (19)
C12—C11—C14	120.9 (2)	N7—C18—C19	118.00 (18)
C13—C12—C11	120.7 (2)	C18—C19—H19A	109.5
C13—C12—H12	119.6	C18—C19—H19B	109.5
C11—C12—H12	119.6	H19A—C19—H19B	109.5
C8—C13—C12	118.1 (3)	C18—C19—H19C	109.5
C8—C13—H13	120.9	H19A—C19—H19C	109.5
C12—C13—H13	120.9	H19B—C19—H19C	109.5
N7—C14—C11	114.02 (17)
C15—N6—N7—C18	−162.76 (18)	C12—C11—C14—N7	−53.9 (3)
C15—N6—N7—C14	14.0 (2)	C10—C11—C14—S2	−117.30 (19)
F1—C8—C9—C10	179.9 (2)	C12—C11—C14—S2	62.6 (2)
C13—C8—C9—C10	−0.5 (4)	C15—S2—C14—N7	15.35 (14)
C8—C9—C10—C11	0.5 (4)	C15—S2—C14—C11	−107.73 (16)
C9—C10—C11—C12	0.1 (3)	N7—N6—C15—N5	−178.19 (17)
C9—C10—C11—C14	180.0 (2)	N7—N6—C15—S2	0.2 (2)
C10—C11—C12—C13	−0.8 (4)	C16—N5—C15—N6	−174.9 (2)
C14—C11—C12—C13	179.4 (2)	C16—N5—C15—S2	6.8 (3)
F1—C8—C13—C12	179.5 (3)	C14—S2—C15—N6	−10.22 (18)
C9—C8—C13—C12	−0.1 (5)	C14—S2—C15—N5	168.13 (18)
C11—C12—C13—C8	0.7 (4)	C15—N5—C16—O3	4.0 (4)
C18—N7—C14—C11	−81.0 (2)	C15—N5—C16—C17	−175.6 (2)
N6—N7—C14—C11	102.1 (2)	N6—N7—C18—O4	179.87 (18)
C18—N7—C14—S2	156.79 (16)	C14—N7—C18—O4	3.2 (3)
N6—N7—C14—S2	−20.1 (2)	N6—N7—C18—C19	−0.6 (3)
C10—C11—C14—N7	126.2 (2)	C14—N7—C18—C19	−177.34 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O4i	0.86	1.96	2.815 (2)	171
C10—H10···O3ii	0.93	2.58	3.267 (3)	131
C17—H17A···O4i	0.96	2.46	3.316 (3)	148
C19—H19B···O4iii	0.96	2.55	3.335 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯O4i	0.86	1.96	2.815 (2)	171
C10—H10⋯O3ii	0.93	2.58	3.267 (3)	131
C17—H17A⋯O4i	0.96	2.46	3.316 (3)	148
C19—H19B⋯O4iii	0.96	2.55	3.335 (3)	139

Symmetry codes: (i) ; (ii) ; (iii) .