N-[4-(4-Bromo-phen-yl)thia-zol-2-yl]-4-(piperidin-1-yl)butanamide.

In the title compound, C(18)H(22)BrN(3)OS, the piperidine ring adopts a chair conformation. The mean plane of the thia-zole ring forms dihedral angles of 23.97 (10) and 75.82 (10)° with the mean planes of its adjacent benzene and piperidine rings, respectively. An intra-molecular N-H⋯N hydrogen bond generates an S(7) ring motif in the mol-ecule. In the crystal, no significant inter-moelcular hydrogen bonds are observed, but a weak π-π inter-action with a centroid-centroid distance of 3.8855 (13) Å occurs.

Related literature

For the pharmacological activity of 2-amino­thia­zole derivatives, see: Lednicer & Mitscher (1977 ▶); Vagdevi et al. (2006 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For further synthetic details, see: El-Subbagh et al. (1999 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H22BrN3OS

M = 408.36

Triclinic,

a = 6.8276 (7) Å

b = 9.2782 (9) Å

c = 14.5907 (14) Å

α = 88.812 (2)°

β = 86.085 (3)°

γ = 75.394 (2)°

V = 892.33 (15) Å3

Z = 2

Mo Kα radiation

μ = 2.43 mm−1

T = 100 K

0.37 × 0.14 × 0.05 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.467, T max = 0.890

17762 measured reflections

5019 independent reflections

4117 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.114

S = 1.07

5019 reflections

221 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.80 e Å−3

Δρmin = −0.86 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019204/hb6767sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019204/hb6767Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019204/hb6767Isup3.cml

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

C18H22BrN3OS	Z = 2
Mr = 408.36	F(000) = 420
Triclinic, P1	Dx = 1.520 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8276 (7) Å	Cell parameters from 5955 reflections
b = 9.2782 (9) Å	θ = 3.1–29.8°
c = 14.5907 (14) Å	µ = 2.43 mm−1
α = 88.812 (2)°	T = 100 K
β = 86.085 (3)°	Plate, colourless
γ = 75.394 (2)°	0.37 × 0.14 × 0.05 mm
V = 892.33 (15) Å3

Bruker APEX DUO CCD area-detector diffractometer	5019 independent reflections
Radiation source: fine-focus sealed tube	4117 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 29.9°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.467, Tmax = 0.890	k = −12→12
17762 measured reflections	l = −20→20

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0683P)2 + 0.091P] where P = (Fo2 + 2Fc2)/3
5019 reflections	(Δ/σ)max = 0.001
221 parameters	Δρmax = 1.80 e Å−3
0 restraints	Δρmin = −0.86 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Br1	0.82800 (4)	0.81297 (2)	0.549438 (15)	0.02561 (9)
S1	0.28942 (9)	0.30257 (5)	0.19656 (4)	0.01885 (13)
O1	−0.0331 (3)	0.31993 (16)	0.09887 (11)	0.0220 (4)
N1	0.2084 (3)	0.56893 (18)	0.26349 (12)	0.0153 (3)
N2	−0.0331 (3)	0.54008 (18)	0.16321 (12)	0.0154 (4)
N3	−0.2166 (3)	0.83694 (18)	0.14310 (12)	0.0154 (4)
C1	0.3846 (4)	0.6922 (2)	0.40953 (15)	0.0197 (4)
H1A	0.2429	0.7288	0.4038	0.024*
C2	0.4825 (4)	0.7643 (2)	0.46664 (15)	0.0221 (5)
H2A	0.4083	0.8490	0.5007	0.027*
C3	0.6911 (4)	0.7117 (2)	0.47378 (15)	0.0187 (4)
C4	0.8022 (4)	0.5877 (2)	0.42470 (14)	0.0191 (4)
H4A	0.9445	0.5532	0.4294	0.023*
C5	0.7013 (4)	0.5153 (2)	0.36861 (14)	0.0180 (4)
H5A	0.7760	0.4298	0.3354	0.022*
C6	0.4927 (3)	0.5654 (2)	0.35987 (13)	0.0142 (4)
C7	0.3892 (3)	0.4898 (2)	0.29872 (14)	0.0155 (4)
C8	0.4539 (4)	0.3451 (2)	0.26968 (15)	0.0197 (4)
H8A	0.5741	0.2770	0.2876	0.024*
C9	0.1412 (3)	0.4853 (2)	0.20874 (14)	0.0146 (4)
C10	−0.1143 (4)	0.4531 (2)	0.11071 (13)	0.0154 (4)
C11	−0.3088 (4)	0.5259 (2)	0.06591 (15)	0.0177 (4)
H11A	−0.3945	0.4541	0.0698	0.021*
H11B	−0.2725	0.5386	−0.0001	0.021*
C12	−0.4417 (4)	0.6759 (2)	0.10078 (15)	0.0189 (4)
H12A	−0.5764	0.6917	0.0754	0.023*
H12B	−0.4621	0.6698	0.1684	0.023*
C13	−0.3601 (4)	0.8121 (2)	0.07711 (15)	0.0190 (4)
H13A	−0.2907	0.7993	0.0149	0.023*
H13B	−0.4754	0.9015	0.0758	0.023*
C14	−0.3271 (4)	0.9117 (2)	0.22672 (15)	0.0189 (4)
H14A	−0.4143	0.8503	0.2553	0.023*
H14B	−0.4158	1.0092	0.2098	0.023*
C15	−0.1798 (4)	0.9352 (2)	0.29574 (15)	0.0231 (5)
H15A	−0.1006	0.8373	0.3172	0.028*
H15B	−0.2573	0.9897	0.3497	0.028*
C16	−0.0344 (4)	1.0234 (2)	0.25308 (16)	0.0231 (5)
H16A	−0.1106	1.1268	0.2402	0.028*
H16B	0.0691	1.0272	0.2967	0.028*
C17	0.0692 (4)	0.9490 (2)	0.16389 (16)	0.0211 (5)
H17A	0.1518	1.0120	0.1332	0.025*
H17B	0.1613	0.8515	0.1782	0.025*
C18	−0.0854 (4)	0.9263 (2)	0.09965 (15)	0.0195 (4)
H18A	−0.1701	1.0244	0.0814	0.023*
H18B	−0.0140	0.8754	0.0434	0.023*
H1N2	−0.083 (5)	0.643 (3)	0.163 (2)	0.031 (8)*

	U11	U22	U33	U12	U13	U23
Br1	0.02680 (16)	0.02875 (14)	0.02536 (13)	−0.01282 (10)	−0.00715 (10)	−0.00372 (9)
S1	0.0190 (3)	0.0121 (2)	0.0252 (3)	−0.0019 (2)	−0.0067 (2)	−0.00195 (18)
O1	0.0235 (9)	0.0153 (7)	0.0278 (8)	−0.0044 (7)	−0.0060 (7)	−0.0037 (6)
N1	0.0127 (9)	0.0143 (7)	0.0193 (8)	−0.0041 (7)	−0.0024 (7)	−0.0009 (6)
N2	0.0123 (9)	0.0126 (7)	0.0220 (8)	−0.0037 (7)	−0.0043 (7)	−0.0018 (6)
N3	0.0147 (9)	0.0136 (7)	0.0187 (8)	−0.0050 (7)	−0.0002 (7)	−0.0003 (6)
C1	0.0156 (11)	0.0191 (9)	0.0237 (10)	−0.0031 (9)	−0.0020 (8)	−0.0008 (8)
C2	0.0205 (12)	0.0209 (9)	0.0248 (10)	−0.0050 (9)	−0.0012 (9)	−0.0036 (8)
C3	0.0215 (12)	0.0210 (9)	0.0175 (9)	−0.0117 (9)	−0.0053 (8)	0.0019 (7)
C4	0.0167 (11)	0.0223 (9)	0.0199 (9)	−0.0070 (9)	−0.0053 (8)	0.0029 (8)
C5	0.0172 (11)	0.0184 (9)	0.0187 (9)	−0.0049 (8)	−0.0020 (8)	0.0003 (7)
C6	0.0145 (10)	0.0143 (8)	0.0156 (8)	−0.0062 (8)	−0.0038 (8)	0.0018 (7)
C7	0.0125 (10)	0.0161 (8)	0.0181 (9)	−0.0043 (8)	−0.0004 (8)	0.0022 (7)
C8	0.0170 (12)	0.0169 (9)	0.0247 (10)	−0.0022 (8)	−0.0061 (9)	0.0004 (7)
C9	0.0133 (10)	0.0131 (8)	0.0178 (8)	−0.0044 (8)	−0.0001 (8)	0.0008 (6)
C10	0.0151 (11)	0.0169 (8)	0.0160 (8)	−0.0076 (8)	0.0003 (8)	0.0000 (7)
C11	0.0147 (11)	0.0174 (9)	0.0225 (9)	−0.0064 (8)	−0.0031 (8)	−0.0014 (7)
C12	0.0158 (11)	0.0190 (9)	0.0222 (10)	−0.0043 (8)	−0.0036 (8)	−0.0011 (7)
C13	0.0168 (11)	0.0171 (9)	0.0240 (10)	−0.0050 (8)	−0.0053 (9)	0.0017 (7)
C14	0.0178 (11)	0.0163 (9)	0.0226 (10)	−0.0061 (8)	0.0050 (9)	−0.0026 (7)
C15	0.0300 (14)	0.0195 (9)	0.0209 (10)	−0.0090 (10)	0.0031 (9)	−0.0032 (8)
C16	0.0243 (13)	0.0198 (9)	0.0269 (11)	−0.0087 (9)	−0.0015 (9)	−0.0039 (8)
C17	0.0156 (11)	0.0171 (9)	0.0322 (11)	−0.0075 (8)	0.0013 (9)	−0.0029 (8)
C18	0.0193 (12)	0.0190 (9)	0.0218 (9)	−0.0088 (9)	0.0022 (8)	−0.0003 (7)

Br1—C3	1.898 (2)	C8—H8A	0.9500
S1—C8	1.720 (2)	C10—C11	1.515 (3)
S1—C9	1.7473 (19)	C11—C12	1.533 (3)
O1—C10	1.231 (2)	C11—H11A	0.9900
N1—C9	1.306 (3)	C11—H11B	0.9900
N1—C7	1.393 (3)	C12—C13	1.529 (3)
N2—C10	1.362 (3)	C12—H12A	0.9900
N2—C9	1.380 (3)	C12—H12B	0.9900
N2—H1N2	0.93 (3)	C13—H13A	0.9900
N3—C18	1.472 (3)	C13—H13B	0.9900
N3—C14	1.478 (3)	C14—C15	1.527 (4)
N3—C13	1.480 (3)	C14—H14A	0.9900
C1—C2	1.383 (3)	C14—H14B	0.9900
C1—C6	1.407 (3)	C15—C16	1.532 (4)
C1—H1A	0.9500	C15—H15A	0.9900
C2—C3	1.394 (4)	C15—H15B	0.9900
C2—H2A	0.9500	C16—C17	1.528 (3)
C3—C4	1.390 (3)	C16—H16A	0.9900
C4—C5	1.389 (3)	C16—H16B	0.9900
C4—H4A	0.9500	C17—C18	1.514 (3)
C5—C6	1.396 (3)	C17—H17A	0.9900
C5—H5A	0.9500	C17—H17B	0.9900
C6—C7	1.466 (3)	C18—H18A	0.9900
C7—C8	1.369 (3)	C18—H18B	0.9900
C8—S1—C9	88.45 (10)	H11A—C11—H11B	106.9
C9—N1—C7	110.70 (17)	C13—C12—C11	116.0 (2)
C10—N2—C9	122.88 (17)	C13—C12—H12A	108.3
C10—N2—H1N2	121 (2)	C11—C12—H12A	108.3
C9—N2—H1N2	116 (2)	C13—C12—H12B	108.3
C18—N3—C14	110.36 (17)	C11—C12—H12B	108.3
C18—N3—C13	109.99 (17)	H12A—C12—H12B	107.4
C14—N3—C13	110.74 (18)	N3—C13—C12	113.05 (17)
C2—C1—C6	120.7 (2)	N3—C13—H13A	109.0
C2—C1—H1A	119.7	C12—C13—H13A	109.0
C6—C1—H1A	119.7	N3—C13—H13B	109.0
C1—C2—C3	119.5 (2)	C12—C13—H13B	109.0
C1—C2—H2A	120.3	H13A—C13—H13B	107.8
C3—C2—H2A	120.3	N3—C14—C15	110.96 (19)
C4—C3—C2	121.1 (2)	N3—C14—H14A	109.4
C4—C3—Br1	119.07 (19)	C15—C14—H14A	109.4
C2—C3—Br1	119.76 (17)	N3—C14—H14B	109.4
C5—C4—C3	118.7 (2)	C15—C14—H14B	109.4
C5—C4—H4A	120.6	H14A—C14—H14B	108.0
C3—C4—H4A	120.6	C14—C15—C16	111.38 (19)
C4—C5—C6	121.5 (2)	C14—C15—H15A	109.4
C4—C5—H5A	119.2	C16—C15—H15A	109.4
C6—C5—H5A	119.2	C14—C15—H15B	109.4
C5—C6—C1	118.5 (2)	C16—C15—H15B	109.4
C5—C6—C7	120.87 (18)	H15A—C15—H15B	108.0
C1—C6—C7	120.6 (2)	C17—C16—C15	109.71 (19)
C8—C7—N1	114.3 (2)	C17—C16—H16A	109.7
C8—C7—C6	126.45 (19)	C15—C16—H16A	109.7
N1—C7—C6	119.23 (17)	C17—C16—H16B	109.7
C7—C8—S1	111.31 (17)	C15—C16—H16B	109.7
C7—C8—H8A	124.3	H16A—C16—H16B	108.2
S1—C8—H8A	124.3	C18—C17—C16	111.1 (2)
N1—C9—N2	121.60 (17)	C18—C17—H17A	109.4
N1—C9—S1	115.24 (16)	C16—C17—H17A	109.4
N2—C9—S1	123.16 (15)	C18—C17—H17B	109.4
O1—C10—N2	121.7 (2)	C16—C17—H17B	109.4
O1—C10—C11	120.4 (2)	H17A—C17—H17B	108.0
N2—C10—C11	117.80 (17)	N3—C18—C17	111.59 (18)
C10—C11—C12	120.40 (18)	N3—C18—H18A	109.3
C10—C11—H11A	107.2	C17—C18—H18A	109.3
C12—C11—H11A	107.2	N3—C18—H18B	109.3
C10—C11—H11B	107.2	C17—C18—H18B	109.3
C12—C11—H11B	107.2	H18A—C18—H18B	108.0
C6—C1—C2—C3	1.0 (3)	C10—N2—C9—N1	−175.4 (2)
C1—C2—C3—C4	−0.2 (3)	C10—N2—C9—S1	5.7 (3)
C1—C2—C3—Br1	178.34 (17)	C8—S1—C9—N1	−0.78 (18)
C2—C3—C4—C5	−0.7 (3)	C8—S1—C9—N2	178.24 (19)
Br1—C3—C4—C5	−179.21 (16)	C9—N2—C10—O1	−1.9 (3)
C3—C4—C5—C6	0.8 (3)	C9—N2—C10—C11	178.70 (19)
C4—C5—C6—C1	0.0 (3)	O1—C10—C11—C12	162.6 (2)
C4—C5—C6—C7	178.56 (19)	N2—C10—C11—C12	−18.0 (3)
C2—C1—C6—C5	−0.9 (3)	C10—C11—C12—C13	73.2 (3)
C2—C1—C6—C7	−179.45 (19)	C18—N3—C13—C12	157.54 (18)
C9—N1—C7—C8	−0.6 (3)	C14—N3—C13—C12	−80.2 (2)
C9—N1—C7—C6	178.28 (19)	C11—C12—C13—N3	−84.7 (2)
C5—C6—C7—C8	23.5 (3)	C18—N3—C14—C15	−58.9 (2)
C1—C6—C7—C8	−158.0 (2)	C13—N3—C14—C15	179.05 (17)
C5—C6—C7—N1	−155.2 (2)	N3—C14—C15—C16	56.3 (2)
C1—C6—C7—N1	23.3 (3)	C14—C15—C16—C17	−52.9 (3)
N1—C7—C8—S1	0.0 (3)	C15—C16—C17—C18	53.2 (2)
C6—C7—C8—S1	−178.77 (17)	C14—N3—C18—C17	59.7 (2)
C9—S1—C8—C7	0.39 (18)	C13—N3—C18—C17	−177.78 (17)
C7—N1—C9—N2	−178.11 (19)	C16—C17—C18—N3	−57.3 (2)
C7—N1—C9—S1	0.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···N3	0.93 (3)	1.83 (3)	2.742 (2)	167 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯N3	0.93 (3)	1.83 (3)	2.742 (2)	167 (3)