2-(4-Fluoro-phen-yl)-4-(4-meth-oxy-phen-yl)-5-(piperidin-1-ylmeth-yl)thia-zole.

In the title compound, C(22)H(23)FN(2)OS, the piperidine ring shows chair confirmation and the two benzene rings make a dihedral angle of 17.0 (6)°. The thia-zole fragment is essentially planar with an r.m.s. deviation of 0.004 (2) Å and a maximum deviation of 0.006 (2) Å.. In the crystal, inter-molecular C-H⋯π inter-actions lead to the formation of a layer structure.

Related literature

For the biological activity of thia­zole derivatives, see: Guo et al. (2006 ▶); Karegoudar et al. (2008 ▶) Reddy et al. (1999 ▶);. For related structures, see: Mitsutaka et al. (2006 ▶); Takayuki et al. (2009 ▶).

Experimental

Crystal data

C22H23FN2OS

M = 382.48

Triclinic,

a = 10.7565 (2) Å

b = 10.8846 (2) Å

c = 11.0179 (2) Å

α = 67.035 (1)°

β = 63.881 (1)°

γ = 60.768 (1)°

V = 985.16 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 296 K

0.26 × 0.26 × 0.24 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.659, T max = 0.746

26568 measured reflections

4674 independent reflections

3614 reflections with I > 2.0σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.110

S = 1.05

4674 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; 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 Iloable, I. DOI: 10.1107/S1600536810054103/pv2365sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054103/pv2365Isup2.hkl

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

C22H23FN2OS	Z = 2
Mr = 382.48	F(000) = 404
Triclinic, P1	Dx = 1.289 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.7565 (2) Å	Cell parameters from 7061 reflections
b = 10.8846 (2) Å	θ = 2.3–27.9°
c = 11.0179 (2) Å	µ = 0.19 mm−1
α = 67.035 (1)°	T = 296 K
β = 63.881 (1)°	Block, colourless
γ = 60.768 (1)°	0.26 × 0.26 × 0.24 mm
V = 985.16 (3) Å3

Bruker APEXII CCD area-detector diffractometer	4674 independent reflections
Radiation source: fine-focus sealed tube	3614 reflections with I > 2.0σ(I)
graphite	Rint = 0.035
φ & ω scans	θmax = 27.9°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −14→14
Tmin = 0.659, Tmax = 0.746	k = −14→14
26568 measured reflections	l = −14→14

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0511P)2 + 0.1593P] where P = (Fo2 + 2Fc2)/3
4674 reflections	(Δ/σ)max = 0.001
245 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.22 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.All hydrogen atoms were located in the calculated sites and included in the final refinement in the riding model approximation with displacement parameters derived from the parent atoms to which they were bonded.

	x	y	z	Uiso*/Ueq
S1	0.33888 (5)	0.75870 (4)	0.04214 (4)	0.05238 (13)
F1	0.59060 (15)	0.58770 (13)	−0.56262 (10)	0.0869 (4)
O1	0.17330 (14)	1.58657 (12)	−0.00821 (13)	0.0640 (3)
N1	0.36970 (13)	0.98214 (12)	−0.14604 (12)	0.0442 (3)
C17	0.22778 (19)	0.90522 (17)	0.24743 (15)	0.0535 (4)
H17A	0.3087	0.8712	0.2844	0.064*
H17B	0.1614	1.0019	0.2622	0.064*
C1	0.1157 (2)	1.70549 (18)	−0.1103 (2)	0.0711 (5)
H1A	0.1916	1.7013	−0.1992	0.107*
H1B	0.0863	1.7941	−0.0869	0.107*
H1C	0.0302	1.7014	−0.1139	0.107*
C2	0.20949 (16)	1.45111 (16)	−0.01833 (16)	0.0479 (3)
C3	0.25260 (17)	1.33858 (17)	0.08932 (15)	0.0503 (3)
H3	0.2557	1.3581	0.1627	0.060*
C4	0.29100 (16)	1.19791 (16)	0.08885 (15)	0.0471 (3)
H4	0.3210	1.1236	0.1614	0.056*
C5	0.28547 (15)	1.16533 (15)	−0.01895 (14)	0.0428 (3)
C6	0.24580 (18)	1.27941 (16)	−0.12758 (15)	0.0527 (4)
H6	0.2446	1.2603	−0.2022	0.063*
C7	0.20801 (19)	1.42074 (17)	−0.12818 (16)	0.0552 (4)
H7	0.1817	1.4950	−0.2023	0.066*
C8	0.31552 (15)	1.01781 (15)	−0.01896 (14)	0.0431 (3)
C9	0.38848 (16)	0.84914 (15)	−0.12873 (14)	0.0438 (3)
C10	0.44413 (15)	0.77917 (15)	−0.24329 (14)	0.0438 (3)
C11	0.43754 (18)	0.86279 (17)	−0.37501 (15)	0.0524 (4)
H11	0.3992	0.9629	−0.3906	0.063*
C12	0.4874 (2)	0.79865 (19)	−0.48320 (16)	0.0595 (4)
H12	0.4839	0.8544	−0.5715	0.071*
C13	0.5419 (2)	0.65120 (19)	−0.45685 (16)	0.0584 (4)
C14	0.5508 (2)	0.56486 (18)	−0.32943 (17)	0.0613 (4)
H14	0.5890	0.4648	−0.3150	0.074*
C15	0.50171 (18)	0.63000 (16)	−0.22271 (16)	0.0539 (4)
H15	0.5073	0.5729	−0.1353	0.065*
C16	0.29129 (17)	0.90992 (15)	0.09436 (14)	0.0470 (3)
N2	0.14491 (14)	0.80983 (13)	0.32118 (12)	0.0468 (3)
C18	0.00257 (19)	0.87436 (18)	0.29190 (16)	0.0571 (4)
H18A	0.0214	0.9003	0.1924	0.068*
H18B	−0.0614	0.9618	0.3268	0.068*
C19	−0.0763 (2)	0.7702 (2)	0.35887 (19)	0.0665 (5)
H19A	−0.0150	0.6851	0.3199	0.080*
H19B	−0.1707	0.8155	0.3394	0.080*
C20	−0.1053 (2)	0.7259 (2)	0.51460 (19)	0.0736 (5)
H20A	−0.1780	0.8084	0.5555	0.088*
H20B	−0.1464	0.6517	0.5548	0.088*
C21	0.0389 (2)	0.6692 (2)	0.54608 (18)	0.0677 (5)
H21A	0.1047	0.5777	0.5188	0.081*
H21B	0.0171	0.6521	0.6452	0.081*
C22	0.11816 (19)	0.77385 (18)	0.47077 (15)	0.0545 (4)
H22A	0.0575	0.8615	0.5057	0.065*
H22B	0.2131	0.7310	0.4888	0.065*

	U11	U22	U33	U12	U13	U23
S1	0.0689 (3)	0.0436 (2)	0.0398 (2)	−0.02424 (18)	−0.00998 (17)	−0.00904 (15)
F1	0.1297 (10)	0.0886 (8)	0.0513 (6)	−0.0570 (7)	−0.0035 (6)	−0.0326 (5)
O1	0.0744 (8)	0.0491 (6)	0.0779 (8)	−0.0251 (6)	−0.0247 (6)	−0.0200 (6)
N1	0.0470 (7)	0.0405 (6)	0.0400 (6)	−0.0140 (5)	−0.0111 (5)	−0.0106 (5)
C17	0.0668 (10)	0.0557 (9)	0.0420 (8)	−0.0297 (8)	−0.0106 (7)	−0.0136 (7)
C1	0.0652 (11)	0.0448 (9)	0.1013 (15)	−0.0165 (8)	−0.0290 (10)	−0.0170 (9)
C2	0.0450 (8)	0.0455 (8)	0.0561 (8)	−0.0192 (6)	−0.0107 (6)	−0.0172 (7)
C3	0.0542 (9)	0.0615 (9)	0.0483 (8)	−0.0292 (7)	−0.0146 (7)	−0.0171 (7)
C4	0.0491 (8)	0.0509 (8)	0.0458 (7)	−0.0220 (7)	−0.0186 (6)	−0.0069 (6)
C5	0.0397 (7)	0.0436 (7)	0.0421 (7)	−0.0150 (6)	−0.0086 (6)	−0.0126 (6)
C6	0.0681 (10)	0.0468 (8)	0.0445 (8)	−0.0185 (7)	−0.0199 (7)	−0.0134 (6)
C7	0.0687 (10)	0.0442 (8)	0.0498 (8)	−0.0172 (7)	−0.0239 (8)	−0.0072 (6)
C8	0.0427 (7)	0.0434 (7)	0.0406 (7)	−0.0150 (6)	−0.0111 (6)	−0.0109 (6)
C9	0.0446 (7)	0.0411 (7)	0.0401 (7)	−0.0141 (6)	−0.0106 (6)	−0.0097 (6)
C10	0.0440 (7)	0.0438 (7)	0.0405 (7)	−0.0172 (6)	−0.0083 (6)	−0.0115 (6)
C11	0.0627 (9)	0.0457 (8)	0.0460 (8)	−0.0214 (7)	−0.0145 (7)	−0.0096 (6)
C12	0.0754 (11)	0.0637 (10)	0.0414 (8)	−0.0331 (9)	−0.0155 (8)	−0.0082 (7)
C13	0.0689 (10)	0.0670 (10)	0.0452 (8)	−0.0350 (9)	−0.0023 (7)	−0.0243 (7)
C14	0.0758 (11)	0.0476 (9)	0.0529 (9)	−0.0231 (8)	−0.0083 (8)	−0.0181 (7)
C15	0.0654 (10)	0.0451 (8)	0.0428 (8)	−0.0184 (7)	−0.0124 (7)	−0.0106 (6)
C16	0.0524 (8)	0.0456 (8)	0.0412 (7)	−0.0198 (7)	−0.0102 (6)	−0.0118 (6)
N2	0.0540 (7)	0.0492 (7)	0.0366 (6)	−0.0219 (6)	−0.0106 (5)	−0.0102 (5)
C18	0.0599 (9)	0.0585 (9)	0.0471 (8)	−0.0178 (8)	−0.0179 (7)	−0.0113 (7)
C19	0.0593 (10)	0.0815 (12)	0.0655 (11)	−0.0297 (9)	−0.0174 (8)	−0.0216 (9)
C20	0.0693 (12)	0.0880 (14)	0.0620 (11)	−0.0436 (10)	−0.0075 (9)	−0.0123 (10)
C21	0.0751 (12)	0.0708 (11)	0.0480 (9)	−0.0359 (10)	−0.0140 (8)	0.0002 (8)
C22	0.0633 (9)	0.0591 (9)	0.0391 (7)	−0.0242 (8)	−0.0135 (7)	−0.0110 (7)

S1—C16	1.7201 (15)	C10—C15	1.388 (2)
S1—C9	1.7264 (14)	C10—C11	1.392 (2)
F1—C13	1.3593 (17)	C11—C12	1.385 (2)
O1—C2	1.3665 (17)	C11—H11	0.9300
O1—C1	1.421 (2)	C12—C13	1.368 (2)
N1—C9	1.3060 (18)	C12—H12	0.9300
N1—C8	1.3912 (17)	C13—C14	1.365 (2)
C17—N2	1.4632 (19)	C14—C15	1.379 (2)
C17—C16	1.5054 (19)	C14—H14	0.9300
C17—H17A	0.9700	C15—H15	0.9300
C17—H17B	0.9700	N2—C22	1.4634 (18)
C1—H1A	0.9600	N2—C18	1.466 (2)
C1—H1B	0.9600	C18—C19	1.512 (2)
C1—H1C	0.9600	C18—H18A	0.9700
C2—C7	1.382 (2)	C18—H18B	0.9700
C2—C3	1.385 (2)	C19—C20	1.518 (3)
C3—C4	1.379 (2)	C19—H19A	0.9700
C3—H3	0.9300	C19—H19B	0.9700
C4—C5	1.3970 (19)	C20—C21	1.510 (3)
C4—H4	0.9300	C20—H20A	0.9700
C5—C6	1.389 (2)	C20—H20B	0.9700
C5—C8	1.4751 (19)	C21—C22	1.517 (2)
C6—C7	1.384 (2)	C21—H21A	0.9700
C6—H6	0.9300	C21—H21B	0.9700
C7—H7	0.9300	C22—H22A	0.9700
C8—C16	1.369 (2)	C22—H22B	0.9700
C9—C10	1.4734 (19)
C16—S1—C9	89.65 (7)	C11—C12—H12	120.9
C2—O1—C1	117.72 (13)	F1—C13—C14	118.51 (15)
C9—N1—C8	110.92 (11)	F1—C13—C12	118.50 (15)
N2—C17—C16	111.16 (12)	C14—C13—C12	122.99 (14)
N2—C17—H17A	109.4	C13—C14—C15	118.20 (15)
C16—C17—H17A	109.4	C13—C14—H14	120.9
N2—C17—H17B	109.4	C15—C14—H14	120.9
C16—C17—H17B	109.4	C14—C15—C10	121.25 (15)
H17A—C17—H17B	108.0	C14—C15—H15	119.4
O1—C1—H1A	109.5	C10—C15—H15	119.4
O1—C1—H1B	109.5	C8—C16—C17	131.87 (13)
H1A—C1—H1B	109.5	C8—C16—S1	110.02 (10)
O1—C1—H1C	109.5	C17—C16—S1	118.06 (11)
H1A—C1—H1C	109.5	C17—N2—C22	111.27 (12)
H1B—C1—H1C	109.5	C17—N2—C18	111.22 (12)
O1—C2—C7	124.48 (14)	C22—N2—C18	110.21 (12)
O1—C2—C3	116.31 (13)	N2—C18—C19	110.86 (13)
C7—C2—C3	119.20 (14)	N2—C18—H18A	109.5
C4—C3—C2	120.72 (13)	C19—C18—H18A	109.5
C4—C3—H3	119.6	N2—C18—H18B	109.5
C2—C3—H3	119.6	C19—C18—H18B	109.5
C3—C4—C5	120.99 (13)	H18A—C18—H18B	108.1
C3—C4—H4	119.5	C18—C19—C20	110.67 (15)
C5—C4—H4	119.5	C18—C19—H19A	109.5
C6—C5—C4	117.27 (13)	C20—C19—H19A	109.5
C6—C5—C8	119.91 (12)	C18—C19—H19B	109.5
C4—C5—C8	122.80 (13)	C20—C19—H19B	109.5
C7—C6—C5	121.99 (14)	H19A—C19—H19B	108.1
C7—C6—H6	119.0	C21—C20—C19	109.97 (15)
C5—C6—H6	119.0	C21—C20—H20A	109.7
C2—C7—C6	119.77 (14)	C19—C20—H20A	109.7
C2—C7—H7	120.1	C21—C20—H20B	109.7
C6—C7—H7	120.1	C19—C20—H20B	109.7
C16—C8—N1	114.69 (12)	H20A—C20—H20B	108.2
C16—C8—C5	127.01 (13)	C20—C21—C22	111.94 (15)
N1—C8—C5	118.26 (12)	C20—C21—H21A	109.2
N1—C9—C10	124.09 (12)	C22—C21—H21A	109.2
N1—C9—S1	114.71 (10)	C20—C21—H21B	109.2
C10—C9—S1	121.19 (10)	C22—C21—H21B	109.2
C15—C10—C11	118.52 (13)	H21A—C21—H21B	107.9
C15—C10—C9	121.36 (13)	N2—C22—C21	111.09 (13)
C11—C10—C9	120.11 (13)	N2—C22—H22A	109.4
C12—C11—C10	120.77 (14)	C21—C22—H22A	109.4
C12—C11—H11	119.6	N2—C22—H22B	109.4
C10—C11—H11	119.6	C21—C22—H22B	109.4
C13—C12—C11	118.27 (15)	H22A—C22—H22B	108.0
C13—C12—H12	120.9
C1—O1—C2—C7	6.7 (2)	C9—C10—C11—C12	−179.05 (14)
C1—O1—C2—C3	−174.43 (14)	C10—C11—C12—C13	0.6 (3)
O1—C2—C3—C4	179.86 (13)	C11—C12—C13—F1	179.83 (15)
C7—C2—C3—C4	−1.2 (2)	C11—C12—C13—C14	−0.8 (3)
C2—C3—C4—C5	−0.9 (2)	F1—C13—C14—C15	179.78 (15)
C3—C4—C5—C6	2.5 (2)	C12—C13—C14—C15	0.4 (3)
C3—C4—C5—C8	−175.70 (13)	C13—C14—C15—C10	0.2 (3)
C4—C5—C6—C7	−2.2 (2)	C11—C10—C15—C14	−0.4 (2)
C8—C5—C6—C7	176.13 (14)	C9—C10—C15—C14	178.63 (15)
O1—C2—C7—C6	−179.58 (14)	N1—C8—C16—C17	−176.66 (15)
C3—C2—C7—C6	1.6 (2)	C5—C8—C16—C17	1.1 (3)
C5—C6—C7—C2	0.1 (3)	N1—C8—C16—S1	0.64 (16)
C9—N1—C8—C16	−1.13 (18)	C5—C8—C16—S1	178.38 (12)
C9—N1—C8—C5	−179.08 (12)	N2—C17—C16—C8	146.91 (16)
C6—C5—C8—C16	−148.99 (16)	N2—C17—C16—S1	−30.21 (18)
C4—C5—C8—C16	29.2 (2)	C9—S1—C16—C8	−0.01 (12)
C6—C5—C8—N1	28.7 (2)	C9—S1—C16—C17	177.71 (13)
C4—C5—C8—N1	−153.12 (13)	C16—C17—N2—C22	164.61 (13)
C8—N1—C9—C10	179.82 (13)	C16—C17—N2—C18	−72.10 (16)
C8—N1—C9—S1	1.11 (16)	C17—N2—C18—C19	175.32 (13)
C16—S1—C9—N1	−0.66 (12)	C22—N2—C18—C19	−60.79 (17)
C16—S1—C9—C10	−179.41 (12)	N2—C18—C19—C20	58.33 (19)
N1—C9—C10—C15	161.52 (15)	C18—C19—C20—C21	−53.4 (2)
S1—C9—C10—C15	−19.8 (2)	C19—C20—C21—C22	52.2 (2)
N1—C9—C10—C11	−19.5 (2)	C17—N2—C22—C21	−177.25 (14)
S1—C9—C10—C11	159.13 (12)	C18—N2—C22—C21	58.89 (17)
C15—C10—C11—C12	0.0 (2)	C20—C21—C22—N2	−55.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cg1C10-C15i	0.96	2.98	3.781 (2)	142
C1—H1C···Cg2C2-C7ii	0.96	2.74	3.595 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯Cg1C10-C15i	0.96	2.98	3.781 (2)	142
C1—H1C⋯Cg2C2-C7ii	0.96	2.74	3.595 (2)	149

Symmetry codes: (i) ; (ii) .