4-Fluoro-N-[3-(2-fluoro-phen-yl)-4-methyl-2,3-dihydro-2-thienyl-idene]benzamide.

In the title compound, C(17)H(12)F(2)N(2)OS, the planar thia-zole ring (r.m.s. deviation = 0.012 Å) makes dihedral angles of 15.08 (9) and 81.81 (6)° with the 4-fluoro-phenyl and 2-fluoro-phenyl rings, respectively. The 2-fluoro-phenyl ring is disordered over two orientations with site-occupancy factors of 0.810 (3) and 0.190 (3). The structure contains inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the biological activity of imino-1,3-thia­zoline derivatives, see: Kim et al. (2007 ▶); Vicini et al. (2006 ▶); Hosseinimehr et al. (2001 ▶); Zhang et al. (2000 ▶); Pietrancosta et al. (2006 ▶). For details of the synthesis, see: Saeed et al. (2008a ▶). For a related structure, see: Saeed et al. (2008b ▶).

Experimental

Crystal data

C17H12F2N2OS

M = 330.35

Orthorhombic,

a = 7.0982 (14) Å

b = 11.423 (2) Å

c = 18.949 (4) Å

V = 1536.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 173 K

0.36 × 0.34 × 0.28 mm

Data collection

Stoe IPDS-II two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T min = 0.920, T max = 0.937

10484 measured reflections

3531 independent reflections

3213 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.082

S = 0.99

3531 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 1491 Friedel pairs

Flack parameter: −0.15 (6)

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022314/bi2375sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022314/bi2375Isup2.hkl

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

C17H12F2N2OS	F(000) = 680
Mr = 330.35	Dx = 1.428 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9675 reflections
a = 7.0982 (14) Å	θ = 3.4–27.8°
b = 11.423 (2) Å	µ = 0.24 mm−1
c = 18.949 (4) Å	T = 173 K
V = 1536.5 (5) Å3	Block, colourless
Z = 4	0.36 × 0.34 × 0.28 mm

Stoe IPDS-II two-circle diffractometer	3531 independent reflections
Radiation source: fine-focus sealed tube	3213 reflections with I > 2σ(I)
graphite	Rint = 0.046
ω scans	θmax = 27.6°, θmin = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −8→9
Tmin = 0.920, Tmax = 0.937	k = −12→14
10484 measured reflections	l = −24→23

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.082	w = 1/[σ2(Fo2) + (0.052P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
3531 reflections	Δρmax = 0.15 e Å−3
219 parameters	Δρmin = −0.26 e Å−3
0 restraints	Absolute structure: Flack (1983), 1491 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.15 (6)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.86255 (5)	0.65177 (5)	0.73205 (2)	0.04103 (12)
N1	0.56925 (19)	0.59033 (13)	0.64274 (7)	0.0316 (3)
O1	0.7594 (2)	0.44060 (14)	0.68401 (8)	0.0520 (4)
F1	0.0840 (3)	0.15356 (14)	0.55262 (9)	0.0825 (5)
F2	0.71228 (15)	0.86728 (14)	0.53579 (6)	0.0406 (4)	0.810 (3)
F2'	0.2818 (7)	0.7551 (6)	0.7021 (3)	0.048 (2)	0.190 (3)
C1	0.6168 (2)	0.47540 (16)	0.65201 (8)	0.0356 (4)
C2	0.67222 (19)	0.66920 (16)	0.67514 (8)	0.0303 (3)
N3	0.63342 (18)	0.78545 (13)	0.66789 (7)	0.0304 (3)
C4	0.7456 (2)	0.86166 (18)	0.70871 (8)	0.0340 (4)
C5	0.8742 (2)	0.80204 (19)	0.74587 (9)	0.0414 (4)
H5	0.9626	0.8381	0.7766	0.050*
C6	0.7117 (3)	0.98996 (19)	0.70565 (10)	0.0436 (4)
H6A	0.7834	1.0287	0.7432	0.065*
H6B	0.5771	1.0056	0.7121	0.065*
H6C	0.7523	1.0201	0.6597	0.065*
C11	0.4788 (3)	0.39042 (17)	0.62212 (8)	0.0353 (4)
C12	0.5145 (3)	0.27036 (19)	0.62624 (10)	0.0451 (4)
H12	0.6301	0.2435	0.6457	0.054*
C13	0.3827 (3)	0.19005 (18)	0.60216 (10)	0.0513 (5)
H13	0.4062	0.1083	0.6052	0.062*
C14	0.2173 (3)	0.2315 (2)	0.57387 (11)	0.0529 (5)
C15	0.1774 (3)	0.3489 (2)	0.56784 (11)	0.0519 (5)
H15	0.0622	0.3747	0.5476	0.062*
C16	0.3098 (3)	0.42878 (17)	0.59203 (10)	0.0405 (4)
H16	0.2854	0.5103	0.5881	0.049*
C21	0.48714 (19)	0.82453 (15)	0.62105 (8)	0.0278 (3)
C22	0.5303 (2)	0.86227 (15)	0.55392 (8)	0.0290 (3)
H22	0.6587	0.8661	0.5400	0.035*	0.190 (3)
C23	0.3925 (2)	0.89464 (15)	0.50637 (8)	0.0325 (3)
H23	0.4250	0.9201	0.4602	0.039*
C24	0.2054 (2)	0.88918 (16)	0.52746 (9)	0.0348 (4)
H24	0.1085	0.9107	0.4954	0.042*
C25	0.1592 (2)	0.8527 (2)	0.59472 (9)	0.0439 (4)
H25	0.0309	0.8499	0.6089	0.053*
C26	0.2997 (2)	0.8203 (2)	0.64164 (9)	0.0403 (4)
H26	0.2675	0.7945	0.6877	0.048*	0.810 (3)

	U11	U22	U33	U12	U13	U23
S1	0.02961 (17)	0.0565 (3)	0.0369 (2)	0.00724 (19)	−0.00870 (15)	0.0061 (2)
N1	0.0334 (6)	0.0324 (8)	0.0290 (6)	0.0029 (5)	−0.0029 (5)	0.0041 (6)
O1	0.0474 (7)	0.0475 (9)	0.0610 (8)	0.0136 (6)	−0.0158 (6)	0.0073 (7)
F1	0.1076 (11)	0.0365 (7)	0.1034 (11)	−0.0068 (8)	−0.0504 (9)	−0.0073 (8)
F2	0.0270 (6)	0.0573 (10)	0.0374 (6)	−0.0039 (5)	0.0046 (4)	0.0079 (6)
F2'	0.032 (3)	0.074 (5)	0.038 (3)	0.005 (3)	0.006 (2)	0.014 (3)
C1	0.0391 (8)	0.0375 (9)	0.0302 (7)	0.0106 (8)	−0.0003 (6)	0.0046 (7)
C2	0.0263 (6)	0.0403 (10)	0.0242 (6)	0.0023 (6)	−0.0005 (5)	0.0036 (6)
N3	0.0260 (5)	0.0362 (7)	0.0290 (6)	−0.0027 (6)	−0.0054 (5)	0.0023 (5)
C4	0.0269 (6)	0.0454 (11)	0.0299 (7)	−0.0076 (7)	−0.0004 (5)	−0.0033 (7)
C5	0.0288 (7)	0.0603 (12)	0.0351 (8)	−0.0059 (7)	−0.0074 (6)	−0.0013 (7)
C6	0.0402 (8)	0.0462 (12)	0.0443 (9)	−0.0112 (8)	−0.0037 (7)	−0.0079 (8)
C11	0.0460 (9)	0.0325 (9)	0.0275 (7)	0.0087 (7)	−0.0001 (6)	0.0021 (6)
C12	0.0590 (11)	0.0372 (10)	0.0391 (9)	0.0129 (9)	−0.0036 (8)	−0.0004 (8)
C13	0.0751 (13)	0.0302 (10)	0.0485 (10)	0.0111 (9)	−0.0098 (10)	−0.0064 (8)
C14	0.0751 (13)	0.0332 (11)	0.0504 (11)	−0.0010 (10)	−0.0168 (10)	−0.0057 (9)
C15	0.0656 (11)	0.0348 (10)	0.0553 (11)	0.0055 (9)	−0.0237 (9)	−0.0007 (10)
C16	0.0525 (10)	0.0295 (9)	0.0395 (8)	0.0064 (7)	−0.0111 (7)	0.0015 (8)
C21	0.0262 (6)	0.0285 (8)	0.0288 (7)	−0.0004 (6)	−0.0037 (5)	0.0016 (6)
C22	0.0280 (6)	0.0278 (8)	0.0314 (7)	−0.0019 (6)	0.0010 (5)	0.0002 (6)
C23	0.0409 (8)	0.0299 (8)	0.0267 (7)	−0.0024 (7)	−0.0022 (6)	0.0021 (6)
C24	0.0335 (7)	0.0363 (9)	0.0346 (8)	0.0029 (7)	−0.0097 (6)	−0.0014 (7)
C25	0.0258 (6)	0.0679 (13)	0.0379 (8)	0.0020 (8)	−0.0020 (6)	0.0010 (9)
C26	0.0290 (7)	0.0615 (13)	0.0305 (7)	−0.0027 (8)	−0.0009 (6)	0.0070 (8)

S1—C5	1.738 (2)	C12—C13	1.388 (3)
S1—C2	1.7400 (15)	C12—H12	0.950
N1—C2	1.313 (2)	C13—C14	1.375 (3)
N1—C1	1.367 (2)	C13—H13	0.950
O1—C1	1.245 (2)	C14—C15	1.376 (3)
F1—C14	1.360 (3)	C15—C16	1.387 (3)
F2—C22	1.3379 (18)	C15—H15	0.950
F2'—C26	1.373 (6)	C16—H16	0.950
C1—C11	1.491 (3)	C21—C22	1.378 (2)
C2—N3	1.363 (2)	C21—C26	1.387 (2)
N3—C4	1.411 (2)	C22—C23	1.380 (2)
N3—C21	1.4370 (18)	C22—H22	0.950
C4—C5	1.339 (2)	C23—C24	1.388 (2)
C4—C6	1.486 (3)	C23—H23	0.950
C5—H5	0.950	C24—C25	1.380 (2)
C6—H6A	0.980	C24—H24	0.950
C6—H6B	0.980	C25—C26	1.386 (2)
C6—H6C	0.980	C25—H25	0.950
C11—C12	1.397 (3)	C26—H26	0.950
C11—C16	1.399 (2)
C5—S1—C2	90.99 (8)	F1—C14—C13	119.0 (2)
C2—N1—C1	117.49 (14)	F1—C14—C15	118.1 (2)
O1—C1—N1	124.75 (18)	C13—C14—C15	122.9 (2)
O1—C1—C11	120.75 (17)	C14—C15—C16	118.31 (19)
N1—C1—C11	114.48 (14)	C14—C15—H15	120.8
N1—C2—N3	120.60 (13)	C16—C15—H15	120.8
N1—C2—S1	130.07 (14)	C15—C16—C11	120.64 (18)
N3—C2—S1	109.32 (12)	C15—C16—H16	119.7
C2—N3—C4	115.58 (14)	C11—C16—H16	119.7
C2—N3—C21	120.72 (13)	C22—C21—C26	118.93 (14)
C4—N3—C21	123.70 (15)	C22—C21—N3	120.45 (13)
C5—C4—N3	111.06 (17)	C26—C21—N3	120.56 (14)
C5—C4—C6	129.23 (16)	F2—C22—C21	117.72 (14)
N3—C4—C6	119.71 (15)	F2—C22—C23	120.34 (14)
C4—C5—S1	113.00 (13)	C21—C22—C23	121.94 (14)
C4—C5—H5	123.5	C21—C22—H22	118.9
S1—C5—H5	123.5	C23—C22—H22	119.1
C4—C6—H6A	109.5	C22—C23—C24	118.55 (15)
C4—C6—H6B	109.5	C22—C23—H23	120.7
H6A—C6—H6B	109.5	C24—C23—H23	120.7
C4—C6—H6C	109.5	C25—C24—C23	120.43 (14)
H6A—C6—H6C	109.5	C25—C24—H24	119.8
H6B—C6—H6C	109.5	C23—C24—H24	119.8
C12—C11—C16	119.08 (18)	C24—C25—C26	120.12 (14)
C12—C11—C1	119.91 (16)	C24—C25—H25	119.9
C16—C11—C1	120.96 (16)	C26—C25—H25	119.9
C13—C12—C11	120.54 (18)	F2'—C26—C25	127.8 (3)
C13—C12—H12	119.7	F2'—C26—C21	110.0 (3)
C11—C12—H12	119.7	C25—C26—C21	120.02 (15)
C14—C13—C12	118.5 (2)	C25—C26—H26	119.9
C14—C13—H13	120.8	C21—C26—H26	120.0
C12—C13—H13	120.8
C2—N1—C1—O1	−6.3 (3)	C12—C13—C14—C15	0.6 (3)
C2—N1—C1—C11	171.87 (14)	F1—C14—C15—C16	177.5 (2)
C1—N1—C2—N3	179.61 (14)	C13—C14—C15—C16	−0.6 (4)
C1—N1—C2—S1	−2.0 (2)	C14—C15—C16—C11	−0.4 (3)
C5—S1—C2—N1	−176.30 (15)	C12—C11—C16—C15	1.3 (3)
C5—S1—C2—N3	2.19 (11)	C1—C11—C16—C15	−176.43 (18)
N1—C2—N3—C4	176.05 (13)	C2—N3—C21—C22	−97.29 (18)
S1—C2—N3—C4	−2.61 (15)	C4—N3—C21—C22	82.51 (19)
N1—C2—N3—C21	−4.1 (2)	C2—N3—C21—C26	80.0 (2)
S1—C2—N3—C21	177.21 (10)	C4—N3—C21—C26	−100.2 (2)
C2—N3—C4—C5	1.65 (19)	C26—C21—C22—F2	178.95 (18)
C21—N3—C4—C5	−178.16 (13)	N3—C21—C22—F2	−3.7 (2)
C2—N3—C4—C6	−178.75 (14)	C26—C21—C22—C23	−0.8 (3)
C21—N3—C4—C6	1.4 (2)	N3—C21—C22—C23	176.59 (16)
N3—C4—C5—S1	0.14 (17)	F2—C22—C23—C24	−179.43 (18)
C6—C4—C5—S1	−179.40 (14)	C21—C22—C23—C24	0.3 (3)
C2—S1—C5—C4	−1.36 (13)	C22—C23—C24—C25	0.4 (3)
O1—C1—C11—C12	−3.8 (3)	C23—C24—C25—C26	−0.5 (3)
N1—C1—C11—C12	177.96 (16)	C24—C25—C26—F2'	−161.8 (4)
O1—C1—C11—C16	173.91 (17)	C24—C25—C26—C21	0.0 (3)
N1—C1—C11—C16	−4.3 (2)	C22—C21—C26—F2'	165.4 (3)
C16—C11—C12—C13	−1.3 (3)	N3—C21—C26—F2'	−12.0 (4)
C1—C11—C12—C13	176.43 (16)	C22—C21—C26—C25	0.6 (3)
C11—C12—C13—C14	0.4 (3)	N3—C21—C26—C25	−176.76 (18)
C12—C13—C14—F1	−177.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1i	0.95	2.41	3.322 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.95	2.41	3.322 (2)	160

Symmetry code: (i) .