2-(4-Fluoro-phen-yl)-N-{4-[6-(4-fluoro-phen-yl)-2,3-dihydro-imidazo[2,1-b][1,3]thia-zol-5-yl]pyridin-2-yl}acetamide.

In the crystal structure of the title compound, C(24)H(18)F(2)N(4)OS, the imidazole system makes dihedral angles of 34.3 (1) and 43.9 (1)°, respectively, with the directly attached 4-fluoro-phenyl and pyridine rings. The crystal structure is stabilized by inter-molecular N-H⋯N hydrogen bonding and by an intra-molecular C-H⋯O hydrogen inter-action. The F atom of the 2-(4-fluoro-phen-yl) group is disordered over two positions with site-occupancy factors of 0.75 and 0.25.

Related literature

For related compounds and their biological relevance, see: Ziegler et al. (2009 ▶).

Experimental

Crystal data

C24H18F2N4OS

M = 448.48

Monoclinic,

a = 4.9179 (3) Å

b = 23.592 (1) Å

c = 18.4834 (9) Å

β = 91.523 (2)°

V = 2143.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 173 K

0.35 × 0.16 × 0.08 mm

Data collection

Bruker SMART APEXII diffractometer

10277 measured reflections

4846 independent reflections

4129 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.090

S = 1.03

4846 reflections

298 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 2197 Friedel pairs

Flack parameter: 0.07 (6)

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810012766/im2189sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012766/im2189Isup2.hkl

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

C24H18F2N4OS	F(000) = 928
Mr = 448.48	Dx = 1.390 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 3757 reflections
a = 4.9179 (3) Å	θ = 2.2–26.4°
b = 23.592 (1) Å	µ = 0.19 mm−1
c = 18.4834 (9) Å	T = 173 K
β = 91.523 (2)°	Plate, yellow
V = 2143.8 (2) Å3	0.35 × 0.16 × 0.08 mm
Z = 4

Bruker SMART APEXII diffractometer	4129 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.028
graphite	θmax = 28.2°, θmin = 1.7°
CCD scan	h = −6→6
10277 measured reflections	k = −30→28
4846 independent reflections	l = −23→24

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0433P)2 + 0.4891P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4846 reflections	Δρmax = 0.23 e Å−3
298 parameters	Δρmin = −0.20 e Å−3
2 restraints	Absolute structure: Flack (1983), 2197 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.07 (6)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.82180 (11)	0.16231 (2)	−0.12400 (3)	0.03583 (14)
F1A	−0.3136 (9)	−0.09848 (19)	0.2022 (2)	0.0837 (13)	0.75
F1B	−0.454 (3)	−0.0837 (5)	0.1902 (9)	0.086 (4)	0.25
F2	0.7391 (4)	0.53748 (6)	0.01213 (10)	0.0609 (4)
C2	0.6645 (6)	0.11864 (10)	−0.05475 (12)	0.0420 (6)
H2A	0.4683	0.1135	−0.0662	0.050*
H2B	0.7517	0.0808	−0.0525	0.050*
C3	0.7039 (6)	0.14935 (9)	0.01721 (11)	0.0386 (6)
H3A	0.5578	0.1394	0.0508	0.046*
H3B	0.8821	0.1398	0.0402	0.046*
N3A	0.6911 (4)	0.20911 (7)	−0.00241 (9)	0.0294 (4)
C4	0.6770 (4)	0.26014 (9)	0.03519 (10)	0.0277 (4)
C5	0.7275 (4)	0.30126 (9)	−0.01557 (10)	0.0266 (4)
N6	0.7779 (4)	0.27699 (7)	−0.08266 (8)	0.0302 (4)
C6A	0.7576 (5)	0.22229 (9)	−0.07094 (10)	0.0301 (4)
C7	0.6335 (4)	0.26246 (8)	0.11346 (10)	0.0264 (4)
C8	0.4394 (4)	0.22883 (9)	0.14539 (10)	0.0265 (4)
H8	0.3224	0.2053	0.1167	0.032*
C9	0.4195 (4)	0.23019 (9)	0.22064 (10)	0.0251 (4)
N10	0.5728 (4)	0.26393 (7)	0.26344 (9)	0.0289 (4)
C11	0.7533 (5)	0.29740 (9)	0.23135 (11)	0.0313 (5)
H11	0.8601	0.3222	0.2610	0.038*
C12	0.7934 (4)	0.29797 (9)	0.15769 (10)	0.0281 (4)
H12	0.9266	0.3220	0.1375	0.034*
N13	0.2423 (4)	0.19595 (7)	0.25989 (8)	0.0269 (4)
H13	0.2720	0.2071	0.3102	0.032*
C14	0.0701 (4)	0.15550 (9)	0.23346 (11)	0.0289 (4)
O15	0.0457 (4)	0.14302 (8)	0.16963 (8)	0.0429 (4)
C16	−0.0944 (5)	0.12612 (10)	0.29138 (11)	0.0328 (5)
H16A	0.0147	0.1247	0.3371	0.039*
H16B	−0.2605	0.1485	0.3002	0.039*
C17	−0.1743 (5)	0.06690 (10)	0.26956 (11)	0.0339 (5)
C18	−0.3773 (6)	0.05731 (15)	0.21804 (14)	0.0533 (7)
H18	−0.4780	0.0881	0.1979	0.064*
C19	−0.4342 (8)	0.00127 (19)	0.19545 (17)	0.0757 (12)
H19	−0.5744	−0.0061	0.1604	0.091*
C20	−0.2856 (9)	−0.04181 (15)	0.22459 (18)	0.0753 (12)
C21	−0.0855 (9)	−0.03416 (13)	0.27436 (18)	0.0693 (10)
H21	0.0149	−0.0654	0.2934	0.083*
C22	−0.0297 (6)	0.02066 (11)	0.29714 (14)	0.0496 (7)
H22	0.1109	0.0268	0.3325	0.060*
C23	0.7289 (4)	0.36344 (8)	−0.00730 (10)	0.0254 (4)
C24	0.5520 (5)	0.39102 (9)	0.03857 (11)	0.0312 (5)
H24	0.4270	0.3695	0.0656	0.037*
C25	0.5560 (5)	0.44968 (10)	0.04538 (12)	0.0379 (5)
H25	0.4361	0.4684	0.0770	0.045*
C26	0.7373 (5)	0.47988 (9)	0.00533 (12)	0.0371 (5)
C27	0.9136 (5)	0.45469 (10)	−0.04073 (12)	0.0383 (5)
H27	1.0359	0.4768	−0.0680	0.046*
C28	0.9095 (5)	0.39598 (9)	−0.04675 (11)	0.0320 (5)
H28	1.0316	0.3777	−0.0782	0.038*

	U11	U22	U33	U12	U13	U23
S1	0.0618 (4)	0.0249 (2)	0.0210 (2)	−0.0009 (3)	0.0078 (2)	−0.0022 (2)
F1A	0.123 (4)	0.061 (3)	0.068 (2)	−0.052 (2)	0.019 (2)	−0.0149 (17)
F1B	0.110 (10)	0.033 (5)	0.113 (9)	−0.036 (6)	−0.005 (8)	−0.016 (5)
F2	0.0845 (12)	0.0243 (7)	0.0745 (11)	−0.0014 (8)	0.0124 (9)	−0.0004 (7)
C2	0.0714 (18)	0.0268 (11)	0.0284 (11)	−0.0066 (11)	0.0095 (11)	0.0002 (9)
C3	0.0685 (17)	0.0239 (11)	0.0234 (10)	−0.0072 (11)	0.0050 (10)	0.0033 (8)
N3A	0.0477 (11)	0.0230 (8)	0.0177 (7)	−0.0027 (8)	0.0049 (7)	0.0016 (6)
C4	0.0364 (11)	0.0260 (10)	0.0209 (9)	−0.0048 (9)	0.0041 (8)	0.0005 (7)
C5	0.0344 (11)	0.0265 (10)	0.0191 (9)	−0.0031 (9)	0.0051 (8)	−0.0002 (7)
N6	0.0458 (11)	0.0254 (9)	0.0196 (8)	−0.0018 (8)	0.0061 (7)	0.0011 (7)
C6A	0.0454 (12)	0.0294 (11)	0.0158 (8)	−0.0029 (10)	0.0046 (8)	−0.0009 (8)
C7	0.0362 (11)	0.0262 (11)	0.0170 (9)	0.0029 (9)	0.0032 (8)	0.0011 (7)
C8	0.0326 (11)	0.0267 (10)	0.0201 (9)	−0.0020 (9)	0.0025 (8)	−0.0009 (7)
C9	0.0321 (11)	0.0240 (10)	0.0194 (9)	0.0031 (8)	0.0056 (8)	0.0002 (7)
N10	0.0414 (11)	0.0277 (9)	0.0179 (7)	−0.0015 (8)	0.0048 (7)	−0.0015 (6)
C11	0.0441 (13)	0.0263 (10)	0.0235 (9)	−0.0045 (9)	0.0013 (9)	−0.0043 (8)
C12	0.0356 (11)	0.0241 (10)	0.0249 (9)	−0.0017 (9)	0.0046 (8)	0.0001 (8)
N13	0.0374 (10)	0.0265 (9)	0.0172 (7)	−0.0021 (8)	0.0071 (7)	0.0009 (6)
C14	0.0314 (11)	0.0313 (11)	0.0240 (9)	0.0022 (9)	0.0015 (8)	0.0049 (8)
O15	0.0533 (10)	0.0536 (11)	0.0219 (7)	−0.0213 (8)	0.0002 (7)	0.0032 (7)
C16	0.0371 (12)	0.0358 (12)	0.0259 (10)	−0.0019 (9)	0.0075 (8)	0.0047 (8)
C17	0.0352 (12)	0.0410 (13)	0.0260 (9)	−0.0113 (10)	0.0089 (8)	0.0041 (9)
C18	0.0392 (14)	0.080 (2)	0.0405 (14)	−0.0095 (14)	0.0002 (11)	−0.0043 (13)
C19	0.069 (2)	0.118 (3)	0.0396 (15)	−0.054 (2)	0.0048 (15)	−0.0204 (18)
C20	0.117 (3)	0.058 (2)	0.0525 (18)	−0.054 (2)	0.027 (2)	−0.0082 (15)
C21	0.112 (3)	0.0334 (15)	0.0633 (18)	−0.0212 (16)	0.0105 (19)	0.0129 (13)
C22	0.0641 (18)	0.0387 (14)	0.0457 (14)	−0.0164 (13)	−0.0073 (12)	0.0132 (11)
C23	0.0330 (10)	0.0254 (10)	0.0177 (8)	−0.0011 (9)	−0.0014 (7)	0.0018 (7)
C24	0.0357 (12)	0.0290 (11)	0.0291 (10)	−0.0002 (9)	0.0056 (9)	0.0063 (8)
C25	0.0435 (13)	0.0351 (12)	0.0352 (12)	0.0086 (10)	0.0053 (10)	0.0003 (9)
C26	0.0521 (14)	0.0205 (10)	0.0384 (12)	−0.0024 (10)	−0.0036 (10)	0.0018 (9)
C27	0.0468 (14)	0.0334 (12)	0.0348 (11)	−0.0126 (10)	0.0026 (10)	0.0074 (9)
C28	0.0381 (13)	0.0320 (12)	0.0263 (10)	−0.0046 (9)	0.0058 (9)	−0.0004 (8)

S1—C6A	1.755 (2)	N13—C14	1.358 (3)
S1—C2	1.831 (2)	N13—H13	0.9732
F1A—C20	1.405 (5)	C14—O15	1.219 (2)
F1B—C20	1.429 (13)	C14—C16	1.526 (3)
F2—C26	1.365 (2)	C16—C17	1.503 (3)
C2—C3	1.522 (3)	C16—H16A	0.9900
C2—H2A	0.9900	C16—H16B	0.9900
C2—H2B	0.9900	C17—C18	1.380 (3)
C3—N3A	1.457 (3)	C17—C22	1.391 (4)
C3—H3A	0.9900	C18—C19	1.412 (5)
C3—H3B	0.9900	C18—H18	0.9500
N3A—C6A	1.353 (2)	C19—C20	1.355 (6)
N3A—C4	1.393 (3)	C19—H19	0.9500
C4—C5	1.377 (3)	C20—C21	1.341 (5)
C4—C7	1.469 (3)	C21—C22	1.385 (4)
C5—N6	1.394 (2)	C21—H21	0.9500
C5—C23	1.475 (3)	C22—H22	0.9500
N6—C6A	1.313 (3)	C23—C24	1.392 (3)
C7—C8	1.385 (3)	C23—C28	1.394 (3)
C7—C12	1.398 (3)	C24—C25	1.390 (3)
C8—C9	1.397 (3)	C24—H24	0.9500
C8—H8	0.9500	C25—C26	1.373 (3)
C9—N10	1.340 (3)	C25—H25	0.9500
C9—N13	1.405 (3)	C26—C27	1.367 (4)
N10—C11	1.338 (3)	C27—C28	1.390 (3)
C11—C12	1.381 (3)	C27—H27	0.9500
C11—H11	0.9500	C28—H28	0.9500
C12—H12	0.9500
C6A—S1—C2	88.70 (10)	O15—C14—C16	121.9 (2)
C3—C2—S1	107.26 (15)	N13—C14—C16	113.82 (17)
C3—C2—H2A	110.3	C17—C16—C14	111.93 (17)
S1—C2—H2A	110.3	C17—C16—H16A	109.2
C3—C2—H2B	110.3	C14—C16—H16A	109.2
S1—C2—H2B	110.3	C17—C16—H16B	109.2
H2A—C2—H2B	108.5	C14—C16—H16B	109.2
N3A—C3—C2	103.86 (16)	H16A—C16—H16B	107.9
N3A—C3—H3A	111.0	C18—C17—C22	118.5 (3)
C2—C3—H3A	111.0	C18—C17—C16	121.1 (2)
N3A—C3—H3B	111.0	C22—C17—C16	120.2 (2)
C2—C3—H3B	111.0	C17—C18—C19	119.4 (3)
H3A—C3—H3B	109.0	C17—C18—H18	120.3
C6A—N3A—C4	106.57 (16)	C19—C18—H18	120.3
C6A—N3A—C3	116.46 (17)	C20—C19—C18	119.0 (3)
C4—N3A—C3	135.62 (17)	C20—C19—H19	120.5
C5—C4—N3A	104.88 (17)	C18—C19—H19	120.5
C5—C4—C7	132.72 (19)	C21—C20—C19	123.3 (3)
N3A—C4—C7	122.28 (17)	C21—C20—F1A	113.2 (4)
C4—C5—N6	110.87 (18)	C19—C20—F1A	123.3 (4)
C4—C5—C23	129.10 (17)	C21—C20—F1B	143.6 (7)
N6—C5—C23	120.02 (16)	C19—C20—F1B	92.4 (6)
C6A—N6—C5	103.95 (15)	C20—C21—C22	118.0 (3)
N6—C6A—N3A	113.68 (17)	C20—C21—H21	121.0
N6—C6A—S1	133.22 (15)	C22—C21—H21	121.0
N3A—C6A—S1	112.93 (15)	C21—C22—C17	121.7 (3)
C8—C7—C12	118.51 (17)	C21—C22—H22	119.2
C8—C7—C4	121.22 (18)	C17—C22—H22	119.2
C12—C7—C4	120.25 (18)	C24—C23—C28	118.57 (19)
C7—C8—C9	118.56 (18)	C24—C23—C5	121.78 (19)
C7—C8—H8	120.7	C28—C23—C5	119.65 (19)
C9—C8—H8	120.7	C25—C24—C23	120.9 (2)
N10—C9—C8	123.24 (19)	C25—C24—H24	119.6
N10—C9—N13	112.57 (16)	C23—C24—H24	119.6
C8—C9—N13	124.18 (18)	C26—C25—C24	118.4 (2)
C11—N10—C9	117.27 (16)	C26—C25—H25	120.8
N10—C11—C12	123.80 (19)	C24—C25—H25	120.8
N10—C11—H11	118.1	F2—C26—C27	119.2 (2)
C12—C11—H11	118.1	F2—C26—C25	118.0 (2)
C11—C12—C7	118.56 (19)	C27—C26—C25	122.8 (2)
C11—C12—H12	120.7	C26—C27—C28	118.4 (2)
C7—C12—H12	120.7	C26—C27—H27	120.8
C14—N13—C9	127.44 (16)	C28—C27—H27	120.8
C14—N13—H13	127.6	C27—C28—C23	121.0 (2)
C9—N13—H13	105.0	C27—C28—H28	119.5
O15—C14—N13	124.24 (19)	C23—C28—H28	119.5
C6A—S1—C2—C3	−27.8 (2)	C4—C7—C12—C11	−177.6 (2)
S1—C2—C3—N3A	33.4 (2)	N10—C9—N13—C14	−176.67 (19)
C2—C3—N3A—C6A	−25.1 (3)	C8—C9—N13—C14	2.2 (3)
C2—C3—N3A—C4	170.3 (2)	C9—N13—C14—O15	0.0 (4)
C6A—N3A—C4—C5	2.2 (2)	C9—N13—C14—C16	−179.99 (19)
C3—N3A—C4—C5	167.9 (3)	O15—C14—C16—C17	27.2 (3)
C6A—N3A—C4—C7	−174.4 (2)	N13—C14—C16—C17	−152.78 (19)
C3—N3A—C4—C7	−8.7 (4)	C14—C16—C17—C18	−74.3 (3)
N3A—C4—C5—N6	−1.3 (2)	C14—C16—C17—C22	100.8 (2)
C7—C4—C5—N6	174.8 (2)	C22—C17—C18—C19	0.6 (4)
N3A—C4—C5—C23	177.6 (2)	C16—C17—C18—C19	175.8 (2)
C7—C4—C5—C23	−6.3 (4)	C17—C18—C19—C20	−0.6 (4)
C4—C5—N6—C6A	−0.2 (3)	C18—C19—C20—C21	0.1 (5)
C23—C5—N6—C6A	−179.2 (2)	C18—C19—C20—F1A	−175.5 (3)
C5—N6—C6A—N3A	1.7 (3)	C18—C19—C20—F1B	172.8 (7)
C5—N6—C6A—S1	−173.1 (2)	C19—C20—C21—C22	0.3 (5)
C4—N3A—C6A—N6	−2.5 (3)	F1A—C20—C21—C22	176.3 (3)
C3—N3A—C6A—N6	−171.4 (2)	F1B—C20—C21—C22	−167.3 (12)
C4—N3A—C6A—S1	173.32 (16)	C20—C21—C22—C17	−0.2 (5)
C3—N3A—C6A—S1	4.5 (3)	C18—C17—C22—C21	−0.2 (4)
C2—S1—C6A—N6	−170.9 (3)	C16—C17—C22—C21	−175.4 (3)
C2—S1—C6A—N3A	14.27 (19)	C4—C5—C23—C24	−34.4 (3)
C5—C4—C7—C8	140.0 (2)	N6—C5—C23—C24	144.5 (2)
N3A—C4—C7—C8	−44.5 (3)	C4—C5—C23—C28	146.3 (2)
C5—C4—C7—C12	−41.6 (4)	N6—C5—C23—C28	−34.9 (3)
N3A—C4—C7—C12	133.9 (2)	C28—C23—C24—C25	−0.4 (3)
C12—C7—C8—C9	−2.5 (3)	C5—C23—C24—C25	−179.7 (2)
C4—C7—C8—C9	175.9 (2)	C23—C24—C25—C26	0.5 (3)
C7—C8—C9—N10	2.4 (3)	C24—C25—C26—F2	179.8 (2)
C7—C8—C9—N13	−176.35 (19)	C24—C25—C26—C27	0.0 (4)
C8—C9—N10—C11	−0.3 (3)	F2—C26—C27—C28	179.8 (2)
N13—C9—N10—C11	178.53 (19)	C25—C26—C27—C28	−0.4 (4)
C9—N10—C11—C12	−1.5 (3)	C26—C27—C28—C23	0.5 (3)
N10—C11—C12—C7	1.3 (3)	C24—C23—C28—C27	−0.1 (3)
C8—C7—C12—C11	0.9 (3)	C5—C23—C28—C27	179.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13···N6i	0.97	2.02	2.980 (2)	171
C8—H8···O15	0.95	2.24	2.845 (3)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N13—H13⋯N6i	0.97	2.02	2.980 (2)	171
C8—H8⋯O15	0.95	2.24	2.845 (3)	120

Symmetry code: (i) .