6-(4-Bromo-phen-yl)-2-(4-fluoro-benz-yl)imidazo[2,1-b][1,3,4]thia-diazole.

In the title compound, C(17)H(11)BrFN(3)S, the imidazothia-diazole and bromo-phenyl rings are individually almost planar, with maximum deviations of 0.0215 (4) and 0.0044 (4) Å, respectively, and are inclined at an angle of 27.34 (3)° with respect to each other. The dihedral angle between the mean planes of the fluoro-benzyl and imidazothia-diazole rings is 79.54 (3)°. The crystal structure is stabilized by inter-molecular C-H⋯N inter-actions resulting in chains of mol-ecules along the b axis.

Related literature

For general background to imidazothia­diazole derivatives, see: Palagiano et al. (1995 ▶). Accumulation of fluorine on carbon leads to increased oxidative and thermal stability, see: Strunecka et al. (2004 ▶); Park et al. (2001 ▶). For related structures, see: Yang et al. (2006 ▶).

Experimental

Crystal data

C17H11BrFN3S

M = 388.26

Monoclinic,

a = 10.505 (4) Å

b = 5.617 (2) Å

c = 25.877 (11) Å

β = 91.566 (7)°

V = 1526.2 (11) Å3

Z = 4

Mo Kα radiation

μ = 2.84 mm−1

T = 296 K

0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.629, T max = 0.659

8589 measured reflections

3308 independent reflections

2419 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.129

S = 1.13

3308 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.86 e Å−3

Δρmin = −0.73 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); 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 CAMERON (Watkin et al., 1996) ▶; software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007343/pv2388sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007343/pv2388Isup2.hkl

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

C17H11BrFN3S	F(000) = 776
Mr = 388.26	Dx = 1.690 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3308 reflections
a = 10.505 (4) Å	θ = 2.1–27.0°
b = 5.617 (2) Å	µ = 2.84 mm−1
c = 25.877 (11) Å	T = 296 K
β = 91.566 (7)°	Block, yellow
V = 1526.2 (11) Å3	0.18 × 0.16 × 0.16 mm
Z = 4

Bruker SMART APEX CCD detector diffractometer	3308 independent reflections
Radiation source: fine-focus sealed tube	2419 reflections with I > 2σ(I)
graphite	Rint = 0.054
ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −13→12
Tmin = 0.629, Tmax = 0.659	k = −6→7
8589 measured reflections	l = −31→33

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.063P)2] where P = (Fo2 + 2Fc2)/3
3308 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.86 e Å−3
0 restraints	Δρmin = −0.73 e Å−3

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
C1	0.1898 (4)	0.6339 (6)	0.36994 (13)	0.0319 (8)
H1A	0.2138	0.4879	0.3877	0.038*
H1B	0.1102	0.6044	0.3512	0.038*
C2	0.2894 (3)	0.6920 (6)	0.33203 (13)	0.0278 (8)
C3	0.4220 (3)	0.8748 (6)	0.26794 (13)	0.0264 (7)
C4	0.5421 (3)	0.5636 (6)	0.25094 (13)	0.0277 (7)
H4	0.5781	0.4124	0.2508	0.033*
C5	0.6754 (3)	0.7708 (6)	0.18420 (13)	0.0253 (7)
C6	0.5751 (3)	0.7565 (6)	0.22174 (13)	0.0258 (8)
C7	0.7627 (3)	0.5856 (6)	0.17813 (13)	0.0291 (8)
H7	0.7562	0.4509	0.1988	0.035*
C8	0.8573 (3)	0.5950 (7)	0.14292 (14)	0.0335 (8)
H8	0.9144	0.4694	0.1400	0.040*
C9	0.8671 (3)	0.7945 (7)	0.11170 (14)	0.0342 (9)
C10	0.7837 (3)	0.9808 (7)	0.11643 (14)	0.0358 (9)
H10	0.7912	1.1151	0.0957	0.043*
C11	0.6881 (3)	0.9679 (6)	0.15221 (14)	0.0323 (8)
H11	0.6312	1.0939	0.1549	0.039*
C12	0.1684 (3)	0.8245 (6)	0.40960 (14)	0.0281 (8)
C13	0.0714 (3)	0.9915 (7)	0.40327 (14)	0.0336 (9)
H13	0.0187	0.9835	0.3739	0.040*
C14	0.0508 (3)	1.1678 (6)	0.43889 (14)	0.0321 (8)
H14	−0.0145	1.2781	0.4341	0.038*
C15	0.1308 (3)	1.1748 (6)	0.48200 (14)	0.0321 (8)
C16	0.2275 (3)	1.0156 (7)	0.49006 (14)	0.0367 (9)
H16	0.2803	1.0256	0.5194	0.044*
C17	0.2456 (3)	0.8396 (6)	0.45377 (14)	0.0346 (9)
H17	0.3107	0.7292	0.4590	0.042*
N1	0.3702 (3)	0.5374 (5)	0.31627 (11)	0.0317 (7)
N2	0.4447 (3)	0.6431 (5)	0.28024 (10)	0.0248 (6)
N3	0.4997 (3)	0.9534 (5)	0.23239 (11)	0.0274 (6)
S1	0.29995 (9)	0.97928 (16)	0.30528 (4)	0.0325 (2)
F1	0.1127 (2)	1.3452 (4)	0.51794 (9)	0.0436 (6)
Br1	0.99661 (4)	0.80778 (9)	0.062488 (15)	0.04750 (19)

	U11	U22	U33	U12	U13	U23
C1	0.039 (2)	0.033 (2)	0.0235 (18)	−0.0102 (16)	0.0011 (15)	0.0006 (15)
C2	0.0358 (19)	0.0223 (18)	0.0250 (18)	−0.0053 (15)	−0.0072 (15)	0.0042 (15)
C3	0.0315 (18)	0.0192 (17)	0.0279 (18)	−0.0006 (13)	−0.0079 (14)	0.0015 (14)
C4	0.0299 (18)	0.0196 (17)	0.0334 (19)	0.0015 (14)	−0.0052 (14)	0.0006 (15)
C5	0.0254 (17)	0.0286 (18)	0.0213 (17)	−0.0046 (14)	−0.0089 (13)	−0.0002 (14)
C6	0.0290 (18)	0.0197 (17)	0.0280 (19)	−0.0023 (13)	−0.0098 (14)	−0.0011 (14)
C7	0.0346 (19)	0.0265 (18)	0.0257 (18)	−0.0016 (15)	−0.0071 (15)	0.0010 (15)
C8	0.0309 (19)	0.036 (2)	0.033 (2)	0.0015 (16)	−0.0093 (15)	−0.0029 (17)
C9	0.0318 (19)	0.043 (2)	0.0275 (19)	−0.0122 (17)	−0.0065 (15)	−0.0046 (17)
C10	0.041 (2)	0.034 (2)	0.032 (2)	−0.0139 (17)	−0.0044 (16)	0.0087 (16)
C11	0.0339 (19)	0.0259 (19)	0.037 (2)	−0.0026 (15)	−0.0061 (16)	0.0064 (16)
C12	0.0257 (17)	0.0280 (19)	0.0303 (19)	−0.0032 (14)	−0.0011 (14)	0.0045 (15)
C13	0.0281 (18)	0.038 (2)	0.034 (2)	−0.0018 (16)	−0.0095 (15)	0.0107 (17)
C14	0.0289 (18)	0.035 (2)	0.032 (2)	0.0088 (16)	0.0037 (14)	0.0109 (16)
C15	0.0358 (19)	0.033 (2)	0.0276 (19)	0.0004 (16)	0.0081 (15)	0.0028 (16)
C16	0.037 (2)	0.042 (2)	0.030 (2)	0.0086 (17)	−0.0110 (16)	−0.0009 (17)
C17	0.0317 (19)	0.037 (2)	0.034 (2)	0.0110 (16)	−0.0053 (15)	0.0007 (16)
N1	0.0389 (17)	0.0267 (16)	0.0293 (17)	−0.0049 (13)	−0.0045 (13)	0.0036 (13)
N2	0.0315 (15)	0.0229 (15)	0.0198 (14)	−0.0028 (11)	−0.0027 (11)	0.0037 (11)
N3	0.0318 (15)	0.0231 (15)	0.0271 (15)	0.0007 (12)	−0.0040 (12)	0.0045 (12)
S1	0.0370 (5)	0.0238 (5)	0.0368 (5)	0.0019 (4)	0.0014 (4)	0.0039 (4)
F1	0.0542 (14)	0.0404 (13)	0.0364 (13)	0.0138 (11)	0.0056 (10)	−0.0061 (10)
Br1	0.0394 (3)	0.0716 (4)	0.0315 (2)	−0.0207 (2)	0.00146 (17)	−0.0057 (2)

C1—C2	1.490 (5)	C8—H8	0.9300
C1—C12	1.504 (5)	C9—C10	1.373 (5)
C1—H1A	0.9700	C9—Br1	1.890 (4)
C1—H1B	0.9700	C10—C11	1.386 (5)
C2—N1	1.288 (4)	C10—H10	0.9300
C2—S1	1.761 (3)	C11—H11	0.9300
C3—N3	1.322 (4)	C12—C17	1.386 (5)
C3—N2	1.360 (4)	C12—C13	1.391 (5)
C3—S1	1.729 (4)	C13—C14	1.374 (5)
C4—N2	1.365 (4)	C13—H13	0.9300
C4—C6	1.371 (5)	C14—C15	1.379 (5)
C4—H4	0.9300	C14—H14	0.9300
C5—C11	1.391 (5)	C15—F1	1.351 (4)
C5—C7	1.399 (5)	C15—C16	1.366 (5)
C5—C6	1.455 (5)	C16—C17	1.380 (5)
C6—N3	1.392 (4)	C16—H16	0.9300
C7—C8	1.368 (5)	C17—H17	0.9300
C7—H7	0.9300	N1—N2	1.369 (4)
C8—C9	1.387 (5)
C2—C1—C12	114.5 (3)	C9—C10—C11	119.7 (3)
C2—C1—H1A	108.6	C9—C10—H10	120.1
C12—C1—H1A	108.6	C11—C10—H10	120.1
C2—C1—H1B	108.6	C10—C11—C5	121.5 (3)
C12—C1—H1B	108.6	C10—C11—H11	119.3
H1A—C1—H1B	107.6	C5—C11—H11	119.3
N1—C2—C1	122.8 (3)	C17—C12—C13	117.8 (3)
N1—C2—S1	116.4 (3)	C17—C12—C1	120.7 (3)
C1—C2—S1	120.8 (3)	C13—C12—C1	121.5 (3)
N3—C3—N2	112.0 (3)	C14—C13—C12	122.4 (3)
N3—C3—S1	139.2 (3)	C14—C13—H13	118.8
N2—C3—S1	108.8 (2)	C12—C13—H13	118.8
N2—C4—C6	104.6 (3)	C13—C14—C15	117.4 (3)
N2—C4—H4	127.7	C13—C14—H14	121.3
C6—C4—H4	127.7	C15—C14—H14	121.3
C11—C5—C7	116.8 (3)	F1—C15—C16	118.5 (3)
C11—C5—C6	121.6 (3)	F1—C15—C14	118.9 (3)
C7—C5—C6	121.5 (3)	C16—C15—C14	122.7 (3)
C4—C6—N3	111.4 (3)	C15—C16—C17	118.7 (3)
C4—C6—C5	127.6 (3)	C15—C16—H16	120.6
N3—C6—C5	121.0 (3)	C17—C16—H16	120.6
C8—C7—C5	122.5 (3)	C16—C17—C12	121.1 (3)
C8—C7—H7	118.8	C16—C17—H17	119.4
C5—C7—H7	118.8	C12—C17—H17	119.4
C7—C8—C9	119.1 (4)	C2—N1—N2	108.5 (3)
C7—C8—H8	120.5	C3—N2—C4	108.2 (3)
C9—C8—H8	120.5	C3—N2—N1	118.3 (3)
C10—C9—C8	120.4 (4)	C4—N2—N1	133.5 (3)
C10—C9—Br1	120.2 (3)	C3—N3—C6	103.8 (3)
C8—C9—Br1	119.4 (3)	C3—S1—C2	87.94 (17)
C12—C1—C2—N1	139.7 (3)	C13—C14—C15—C16	0.1 (6)
C12—C1—C2—S1	−41.6 (4)	F1—C15—C16—C17	179.3 (3)
N2—C4—C6—N3	−0.1 (4)	C14—C15—C16—C17	−0.4 (6)
N2—C4—C6—C5	179.0 (3)	C15—C16—C17—C12	0.7 (6)
C11—C5—C6—C4	171.4 (3)	C13—C12—C17—C16	−0.5 (6)
C7—C5—C6—C4	−7.8 (5)	C1—C12—C17—C16	179.2 (3)
C11—C5—C6—N3	−9.6 (5)	C1—C2—N1—N2	177.4 (3)
C7—C5—C6—N3	171.3 (3)	S1—C2—N1—N2	−1.3 (4)
C11—C5—C7—C8	0.5 (5)	N3—C3—N2—C4	−0.5 (4)
C6—C5—C7—C8	179.7 (3)	S1—C3—N2—C4	−179.3 (2)
C5—C7—C8—C9	−0.5 (5)	N3—C3—N2—N1	−179.4 (3)
C7—C8—C9—C10	0.6 (5)	S1—C3—N2—N1	1.8 (3)
C7—C8—C9—Br1	−179.4 (2)	C6—C4—N2—C3	0.3 (3)
C8—C9—C10—C11	−0.8 (5)	C6—C4—N2—N1	179.0 (3)
Br1—C9—C10—C11	179.2 (3)	C2—N1—N2—C3	−0.4 (4)
C9—C10—C11—C5	0.9 (5)	C2—N1—N2—C4	−178.9 (3)
C7—C5—C11—C10	−0.7 (5)	N2—C3—N3—C6	0.4 (4)
C6—C5—C11—C10	−179.9 (3)	S1—C3—N3—C6	178.7 (3)
C2—C1—C12—C17	−83.6 (4)	C4—C6—N3—C3	−0.2 (4)
C2—C1—C12—C13	96.2 (4)	C5—C6—N3—C3	−179.4 (3)
C17—C12—C13—C14	0.2 (5)	N3—C3—S1—C2	179.7 (4)
C1—C12—C13—C14	−179.6 (3)	N2—C3—S1—C2	−1.9 (2)
C12—C13—C14—C15	0.1 (5)	N1—C2—S1—C3	2.0 (3)
C13—C14—C15—F1	−179.7 (3)	C1—C2—S1—C3	−176.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···N3i	0.97	2.57	3.423 (5)	147
C4—H4···N3ii	0.93	2.74	3.488 (5)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯N3i	0.97	2.57	3.423 (5)	147
C4—H4⋯N3ii	0.93	2.74	3.488 (5)	137

Symmetry codes: (i) ; (ii) .