2-(1H-Imidazol-1-yl)-4-[3-(trifluoro-meth-yl)phen-yl]-1,3-thia-zole.

The title compound, C(13)H(8)F(3)N(3)S, consists of three linked aromatic rings. The whole mol-ecule (except for the three F atoms) is planar to within 0.225 (2) Å. In the crystal, adjacent mol-ecules are linked into chains along the ac diagonal by weak C-H⋯N inter-actions.

Related literature

For general background to the synthesis of imidazolo­thia­zoles by copper-catalysed coupling, see: Zhu et al. (2007 ▶).

Experimental

Crystal data

C13H8F3N3S

M = 295.28

Monoclinic,

a = 8.4152 (7) Å

b = 19.2403 (15) Å

c = 8.4105 (7) Å

β = 114.210 (1)°

V = 1241.98 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 150 K

0.40 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.893, T max = 0.972

9797 measured reflections

2716 independent reflections

2164 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.103

S = 1.07

2716 reflections

213 parameters

All H-atom parameters refined

Δρmax = 0.27 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000615/ff2095sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000615/ff2095Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813000615/ff2095Isup3.cml

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

C13H8F3N3S	F(000) = 600
Mr = 295.28	Dx = 1.579 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1717 reflections
a = 8.4152 (7) Å	θ = 3.1–24.5°
b = 19.2403 (15) Å	µ = 0.29 mm−1
c = 8.4105 (7) Å	T = 150 K
β = 114.210 (1)°	Block, colourless
V = 1241.98 (18) Å3	0.40 × 0.20 × 0.10 mm
Z = 4

Bruker SMART APEXII diffractometer	2716 independent reflections
Radiation source: fine-focus sealed tube	2164 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→9
Tmin = 0.893, Tmax = 0.972	k = −24→24
9797 measured reflections	l = −10→10

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: difference Fourier map
wR(F2) = 0.103	All H-atom parameters refined
S = 1.07	w = 1/[σ2(Fo2) + (0.0429P)2 + 0.2754P] where P = (Fo2 + 2Fc2)/3
2716 reflections	(Δ/σ)max < 0.001
213 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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
S1	0.22949 (6)	0.55985 (2)	0.40649 (6)	0.02492 (15)
N1	0.0577 (2)	0.44567 (7)	0.36963 (19)	0.0214 (3)
N2	−0.0844 (2)	0.52744 (7)	0.14612 (18)	0.0207 (3)
N3	−0.3431 (2)	0.52646 (9)	−0.0761 (2)	0.0306 (4)
F1	0.62622 (19)	0.32402 (8)	1.15343 (17)	0.0571 (4)
F2	0.64762 (19)	0.22590 (6)	1.0452 (2)	0.0571 (4)
F3	0.74065 (16)	0.31841 (7)	0.97113 (19)	0.0530 (4)
C1	0.2432 (2)	0.37530 (9)	0.6250 (2)	0.0215 (4)
C2	0.4056 (3)	0.36375 (10)	0.7611 (2)	0.0234 (4)
C3	0.4358 (3)	0.30371 (9)	0.8600 (2)	0.0250 (4)
C4	0.3055 (3)	0.25486 (10)	0.8277 (3)	0.0277 (4)
C5	0.1440 (3)	0.26582 (10)	0.6924 (3)	0.0288 (5)
C6	0.1129 (3)	0.32528 (10)	0.5908 (3)	0.0256 (4)
C7	0.6105 (3)	0.29265 (10)	1.0058 (3)	0.0331 (5)
C8	0.2102 (2)	0.43953 (9)	0.5201 (2)	0.0204 (4)
C9	0.3176 (3)	0.49573 (9)	0.5588 (2)	0.0240 (4)
C10	0.0540 (2)	0.50577 (9)	0.2999 (2)	0.0205 (4)
C11	−0.2399 (3)	0.49374 (10)	0.0647 (2)	0.0285 (5)
C12	−0.2503 (3)	0.58436 (11)	−0.0854 (3)	0.0286 (4)
C13	−0.0922 (3)	0.58620 (10)	0.0485 (2)	0.0266 (4)
H9	0.425 (3)	0.5042 (10)	0.656 (3)	0.028 (5)*
H6	0.004 (3)	0.3331 (10)	0.496 (3)	0.028 (5)*
H2	0.489 (3)	0.3964 (11)	0.783 (3)	0.031 (6)*
H11	−0.263 (3)	0.4517 (11)	0.113 (3)	0.035 (6)*
H5	0.053 (3)	0.2292 (11)	0.670 (3)	0.040 (6)*
H4	0.328 (3)	0.2144 (11)	0.900 (3)	0.037 (6)*
H12	−0.298 (3)	0.6159 (12)	−0.176 (3)	0.043 (7)*
H13	0.002 (3)	0.6192 (12)	0.080 (3)	0.044 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0198 (3)	0.0248 (2)	0.0255 (3)	−0.00220 (19)	0.00454 (19)	0.00161 (18)
N1	0.0189 (8)	0.0255 (8)	0.0196 (8)	0.0012 (6)	0.0077 (6)	−0.0024 (6)
N2	0.0192 (8)	0.0238 (7)	0.0172 (7)	0.0011 (6)	0.0055 (6)	−0.0012 (6)
N3	0.0268 (9)	0.0364 (9)	0.0214 (8)	−0.0014 (7)	0.0028 (7)	0.0014 (7)
F1	0.0494 (9)	0.0731 (10)	0.0318 (7)	0.0124 (8)	−0.0007 (6)	−0.0037 (7)
F2	0.0446 (9)	0.0321 (7)	0.0713 (10)	0.0094 (6)	0.0003 (7)	0.0201 (6)
F3	0.0223 (7)	0.0689 (10)	0.0589 (9)	0.0053 (6)	0.0076 (6)	0.0279 (7)
C1	0.0230 (10)	0.0223 (9)	0.0209 (9)	0.0020 (7)	0.0107 (8)	−0.0022 (7)
C2	0.0210 (10)	0.0251 (9)	0.0244 (10)	0.0001 (8)	0.0096 (8)	−0.0013 (7)
C3	0.0256 (11)	0.0233 (9)	0.0250 (10)	0.0028 (8)	0.0094 (8)	0.0007 (7)
C4	0.0315 (11)	0.0222 (9)	0.0319 (11)	0.0007 (8)	0.0155 (9)	0.0025 (8)
C5	0.0257 (11)	0.0260 (10)	0.0361 (11)	−0.0043 (8)	0.0142 (9)	−0.0040 (8)
C6	0.0214 (10)	0.0273 (10)	0.0270 (10)	−0.0003 (8)	0.0088 (8)	−0.0046 (8)
C7	0.0315 (12)	0.0276 (10)	0.0357 (12)	0.0029 (9)	0.0092 (9)	0.0084 (8)
C8	0.0176 (9)	0.0250 (9)	0.0186 (9)	0.0028 (7)	0.0074 (7)	−0.0018 (7)
C9	0.0198 (10)	0.0267 (10)	0.0229 (9)	0.0014 (8)	0.0059 (8)	0.0008 (7)
C10	0.0179 (9)	0.0257 (9)	0.0176 (9)	0.0005 (7)	0.0068 (7)	−0.0029 (7)
C11	0.0274 (11)	0.0297 (10)	0.0220 (10)	−0.0044 (8)	0.0037 (8)	−0.0012 (8)
C12	0.0307 (11)	0.0316 (10)	0.0224 (10)	0.0043 (9)	0.0099 (8)	0.0034 (8)
C13	0.0259 (11)	0.0282 (10)	0.0255 (10)	−0.0005 (8)	0.0104 (8)	0.0036 (8)

S1—C9	1.7128 (19)	C2—C3	1.385 (3)
S1—C10	1.7266 (18)	C2—H2	0.90 (2)
N1—C10	1.291 (2)	C3—C4	1.384 (3)
N1—C8	1.390 (2)	C3—C7	1.494 (3)
N2—C11	1.367 (2)	C4—C5	1.385 (3)
N2—C13	1.383 (2)	C4—H4	0.96 (2)
N2—C10	1.403 (2)	C5—C6	1.387 (3)
N3—C11	1.307 (2)	C5—H5	1.00 (2)
N3—C12	1.381 (3)	C6—H6	0.95 (2)
F1—C7	1.337 (3)	C8—C9	1.360 (3)
F2—C7	1.331 (2)	C9—H9	0.95 (2)
F3—C7	1.339 (3)	C11—H11	0.96 (2)
C1—C2	1.394 (3)	C12—C13	1.346 (3)
C1—C6	1.397 (3)	C12—H12	0.93 (2)
C1—C8	1.477 (2)	C13—H13	0.96 (2)
C9—S1—C10	88.27 (9)	F2—C7—F1	106.30 (17)
C10—N1—C8	109.34 (15)	F2—C7—F3	106.36 (18)
C11—N2—C13	106.72 (15)	F1—C7—F3	104.87 (18)
C11—N2—C10	125.71 (16)	F2—C7—C3	113.16 (17)
C13—N2—C10	127.57 (16)	F1—C7—C3	112.79 (18)
C11—N3—C12	105.01 (17)	F3—C7—C3	112.71 (17)
C2—C1—C6	118.77 (17)	C9—C8—N1	115.14 (16)
C2—C1—C8	120.30 (17)	C9—C8—C1	125.36 (16)
C6—C1—C8	120.93 (17)	N1—C8—C1	119.50 (16)
C3—C2—C1	120.20 (18)	C8—C9—S1	110.65 (14)
C3—C2—H2	121.4 (13)	C8—C9—H9	130.2 (12)
C1—C2—H2	118.4 (13)	S1—C9—H9	119.0 (12)
C4—C3—C2	120.85 (18)	N1—C10—N2	122.77 (16)
C4—C3—C7	119.88 (17)	N1—C10—S1	116.59 (13)
C2—C3—C7	119.25 (17)	N2—C10—S1	120.64 (13)
C3—C4—C5	119.30 (18)	N3—C11—N2	111.68 (18)
C3—C4—H4	119.6 (14)	N3—C11—H11	128.1 (13)
C5—C4—H4	121.1 (14)	N2—C11—H11	120.2 (13)
C4—C5—C6	120.36 (19)	C13—C12—N3	111.19 (17)
C4—C5—H5	117.8 (13)	C13—C12—H12	128.0 (14)
C6—C5—H5	121.8 (13)	N3—C12—H12	120.8 (14)
C5—C6—C1	120.50 (18)	C12—C13—N2	105.38 (17)
C5—C6—H6	121.5 (12)	C12—C13—H13	131.8 (14)
C1—C6—H6	118.0 (12)	N2—C13—H13	122.8 (14)
C6—C1—C2—C3	−0.1 (3)	C2—C1—C8—N1	170.46 (17)
C8—C1—C2—C3	179.52 (17)	C6—C1—C8—N1	−9.9 (3)
C1—C2—C3—C4	−1.0 (3)	N1—C8—C9—S1	0.5 (2)
C1—C2—C3—C7	−179.66 (18)	C1—C8—C9—S1	−178.79 (15)
C2—C3—C4—C5	1.2 (3)	C10—S1—C9—C8	−0.46 (15)
C7—C3—C4—C5	179.87 (19)	C8—N1—C10—N2	−179.81 (16)
C3—C4—C5—C6	−0.3 (3)	C8—N1—C10—S1	−0.2 (2)
C4—C5—C6—C1	−0.8 (3)	C11—N2—C10—N1	9.5 (3)
C2—C1—C6—C5	1.0 (3)	C13—N2—C10—N1	−171.01 (18)
C8—C1—C6—C5	−178.61 (18)	C11—N2—C10—S1	−170.05 (15)
C4—C3—C7—F2	26.1 (3)	C13—N2—C10—S1	9.4 (3)
C2—C3—C7—F2	−155.26 (19)	C9—S1—C10—N1	0.41 (16)
C4—C3—C7—F1	−94.6 (2)	C9—S1—C10—N2	180.00 (16)
C2—C3—C7—F1	84.0 (2)	C12—N3—C11—N2	−0.4 (2)
C4—C3—C7—F3	146.84 (19)	C13—N2—C11—N3	0.4 (2)
C2—C3—C7—F3	−34.5 (3)	C10—N2—C11—N3	180.00 (17)
C10—N1—C8—C9	−0.2 (2)	C11—N3—C12—C13	0.2 (2)
C10—N1—C8—C1	179.13 (16)	N3—C12—C13—N2	0.0 (2)
C2—C1—C8—C9	−10.3 (3)	C11—N2—C13—C12	−0.3 (2)
C6—C1—C8—C9	169.30 (18)	C10—N2—C13—C12	−179.81 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N3i	0.95 (2)	2.34 (2)	3.278 (2)	169.4 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯N3i	0.95 (2)	2.34 (2)	3.278 (2)	169.4 (18)

Symmetry code: (i) .