2-[(2,6-Dichloro-benz-yl)amino]-N-(4-methyl-thia-zol-2-yl)acetamide.

In the title compound, C(13)H(13)Cl(2)N(3)OS, the thia-zole and benzene rings are roughly parallel to one another in two layers [dihedral angle = 5.08 (2)°] because the N-C-C-N-C chain that links the two rings is folded [N-C-C-N torsion angle = 12.0 (2)°] rather than fully extended. An intra-molecular N-H⋯N inter-action occurs. In the crystal, weak inter-molecular N-H⋯N and C-H⋯O inter-actions are present and π-π inter-actions are indicated by the short distances [3.507 (3)-3.665 (2) Å] between the centroids of the thia-zole and benzene rings.

Related literature

For details of the biological activity of Dipeptidyl peptidase IV (DPP-IV) inhibitors, see: Cheon et al. (2005 ▶); Kondo et al. (2007 ▶); Sakashita et al. (2006 ▶); Zhan et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H13Cl2N3OS

M = 330.22

Monoclinic,

a = 14.008 (4) Å

b = 18.133 (5) Å

c = 11.390 (3) Å

β = 97.341 (3)°

V = 2869.4 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.60 mm−1

T = 113 K

0.22 × 0.18 × 0.16 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T min = 0.880, T max = 0.911

11103 measured reflections

3371 independent reflections

3150 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.131

S = 1.20

3371 reflections

191 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.65 e Å−3

Δρmin = −0.83 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 I, global. DOI: 10.1107/S1600536810003089/fl2286sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003089/fl2286Isup2.hkl

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

C13H13Cl2N3OS	F(000) = 1360
Mr = 330.22	Dx = 1.529 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -C 2yc	Cell parameters from 5153 reflections
a = 14.008 (4) Å	θ = 1.8–27.9°
b = 18.133 (5) Å	µ = 0.60 mm−1
c = 11.390 (3) Å	T = 113 K
β = 97.341 (3)°	Prism, colorless
V = 2869.4 (14) Å3	0.22 × 0.18 × 0.16 mm
Z = 8

Rigaku Saturn diffractometer	3371 independent reflections
Radiation source: rotating anode	3150 reflections with I > 2σ(I)
multilayer	Rint = 0.036
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 1.9°
ω and φ scans	h = −18→18
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −23→18
Tmin = 0.880, Tmax = 0.911	l = −13→14
11103 measured reflections

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)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.0837P)2 + 0.6909P] where P = (Fo2 + 2Fc2)/3
S = 1.20	(Δ/σ)max < 0.001
3371 reflections	Δρmax = 0.65 e Å−3
191 parameters	Δρmin = −0.83 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.086 (3)

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
Cl1	0.59889 (3)	0.30694 (2)	0.64087 (4)	0.03507 (18)
Cl2	0.60026 (3)	0.00844 (2)	0.65202 (3)	0.03000 (17)
S1	0.60179 (3)	0.37651 (2)	0.15270 (3)	0.02879 (17)
O1	0.59946 (9)	0.22476 (8)	0.16770 (10)	0.0371 (3)
N2	0.65223 (10)	0.28348 (8)	0.33975 (11)	0.0262 (3)
N1	0.66017 (10)	0.41118 (7)	0.37000 (11)	0.0260 (3)
N3	0.66669 (9)	0.15932 (7)	0.46748 (11)	0.0244 (3)
C1	0.64101 (10)	0.35505 (9)	0.29875 (12)	0.0242 (3)
C2	0.64316 (12)	0.47666 (9)	0.30816 (14)	0.0284 (3)
C3	0.61282 (13)	0.46827 (10)	0.19104 (15)	0.0325 (4)
H3A	0.5994	0.5080	0.1370	0.039*
C4	0.65614 (15)	0.54732 (10)	0.37486 (15)	0.0368 (4)
H4A	0.6702	0.5869	0.3211	0.055*
H4B	0.7097	0.5425	0.4387	0.055*
H4C	0.5971	0.5590	0.4087	0.055*
C5	0.63006 (11)	0.22221 (9)	0.27318 (13)	0.0282 (4)
C6	0.64796 (12)	0.15012 (9)	0.33971 (13)	0.0290 (4)
H6A	0.5911	0.1178	0.3207	0.035*
H6B	0.7037	0.1250	0.3119	0.035*
C7	0.57765 (11)	0.15610 (8)	0.52297 (13)	0.0239 (3)
H7A	0.5421	0.1103	0.4986	0.029*
H7B	0.5360	0.1986	0.4964	0.029*
C8	0.60135 (10)	0.15779 (8)	0.65549 (12)	0.0216 (3)
C9	0.61402 (11)	0.22376 (8)	0.71857 (13)	0.0251 (3)
C10	0.63758 (11)	0.22652 (10)	0.84107 (14)	0.0299 (4)
H10	0.6454	0.2726	0.8809	0.036*
C11	0.64947 (12)	0.16110 (10)	0.90375 (14)	0.0299 (4)
H11	0.6655	0.1622	0.9873	0.036*
C12	0.63813 (11)	0.09389 (9)	0.84525 (14)	0.0275 (3)
H12	0.6462	0.0488	0.8880	0.033*
C13	0.61481 (10)	0.09381 (8)	0.72306 (13)	0.0232 (3)
H2	0.6752 (16)	0.2782 (14)	0.411 (2)	0.049 (6)*
H3	0.7065 (14)	0.1245 (11)	0.5004 (18)	0.030 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0473 (3)	0.0242 (2)	0.0324 (3)	−0.00894 (14)	−0.0001 (2)	0.00170 (13)
Cl2	0.0396 (3)	0.0237 (3)	0.0275 (3)	−0.00282 (13)	0.00714 (17)	0.00110 (12)
S1	0.0322 (3)	0.0420 (3)	0.0119 (2)	−0.00337 (14)	0.00174 (16)	0.00325 (13)
O1	0.0493 (8)	0.0486 (8)	0.0121 (5)	−0.0193 (5)	−0.0016 (5)	−0.0025 (5)
N2	0.0355 (7)	0.0315 (7)	0.0105 (6)	−0.0120 (5)	−0.0011 (5)	0.0016 (5)
N1	0.0302 (7)	0.0323 (7)	0.0157 (6)	−0.0046 (5)	0.0031 (5)	0.0022 (5)
N3	0.0305 (7)	0.0278 (7)	0.0147 (6)	−0.0082 (5)	0.0028 (5)	−0.0007 (4)
C1	0.0244 (7)	0.0353 (8)	0.0131 (7)	−0.0071 (6)	0.0029 (5)	0.0024 (5)
C2	0.0309 (8)	0.0345 (8)	0.0211 (8)	0.0034 (6)	0.0079 (6)	0.0043 (6)
C3	0.0397 (9)	0.0384 (9)	0.0200 (8)	0.0065 (7)	0.0066 (6)	0.0064 (6)
C4	0.0546 (11)	0.0321 (8)	0.0253 (8)	0.0080 (7)	0.0110 (7)	0.0037 (6)
C5	0.0331 (8)	0.0380 (8)	0.0134 (7)	−0.0158 (6)	0.0027 (6)	−0.0025 (6)
C6	0.0411 (9)	0.0298 (8)	0.0161 (8)	−0.0137 (6)	0.0033 (6)	−0.0048 (6)
C7	0.0282 (7)	0.0285 (8)	0.0146 (7)	−0.0088 (5)	0.0007 (5)	0.0015 (5)
C8	0.0222 (7)	0.0265 (8)	0.0160 (7)	−0.0061 (5)	0.0016 (5)	0.0002 (5)
C9	0.0271 (7)	0.0277 (7)	0.0201 (7)	−0.0056 (5)	0.0008 (6)	0.0005 (5)
C10	0.0297 (8)	0.0367 (8)	0.0226 (8)	−0.0045 (6)	0.0007 (6)	−0.0084 (6)
C11	0.0273 (8)	0.0471 (10)	0.0147 (7)	−0.0007 (6)	0.0007 (6)	−0.0007 (6)
C12	0.0262 (7)	0.0378 (9)	0.0190 (7)	0.0009 (6)	0.0042 (6)	0.0064 (6)
C13	0.0236 (7)	0.0272 (7)	0.0192 (7)	−0.0035 (5)	0.0044 (5)	0.0009 (5)

Cl1—C9	1.7480 (16)	C4—H4B	0.9800
Cl2—C13	1.7465 (16)	C4—H4C	0.9800
S1—C3	1.7222 (19)	C5—C6	1.516 (2)
S1—C1	1.7282 (15)	C6—H6A	0.9900
O1—C5	1.2238 (19)	C6—H6B	0.9900
N2—C5	1.359 (2)	C7—C8	1.5038 (19)
N2—C1	1.381 (2)	C7—H7A	0.9900
N2—H2	0.84 (2)	C7—H7B	0.9900
N1—C1	1.308 (2)	C8—C13	1.392 (2)
N1—C2	1.385 (2)	C8—C9	1.395 (2)
N3—C6	1.4550 (19)	C9—C10	1.393 (2)
N3—C7	1.470 (2)	C10—C11	1.384 (3)
N3—H3	0.89 (2)	C10—H10	0.9500
C2—C3	1.356 (2)	C11—C12	1.388 (2)
C2—C4	1.489 (3)	C11—H11	0.9500
C3—H3A	0.9500	C12—C13	1.388 (2)
C4—H4A	0.9800	C12—H12	0.9500
C3—S1—C1	88.07 (8)	C5—C6—H6A	108.9
C5—N2—C1	124.86 (13)	N3—C6—H6B	108.9
C5—N2—H2	118.5 (17)	C5—C6—H6B	108.9
C1—N2—H2	116.6 (17)	H6A—C6—H6B	107.7
C1—N1—C2	110.07 (13)	N3—C7—C8	109.89 (11)
C6—N3—C7	111.78 (12)	N3—C7—H7A	109.7
C6—N3—H3	111.3 (13)	C8—C7—H7A	109.7
C7—N3—H3	108.1 (13)	N3—C7—H7B	109.7
N1—C1—N2	121.05 (13)	C8—C7—H7B	109.7
N1—C1—S1	115.90 (12)	H7A—C7—H7B	108.2
N2—C1—S1	123.05 (11)	C13—C8—C9	115.51 (13)
C3—C2—N1	114.58 (15)	C13—C8—C7	122.35 (13)
C3—C2—C4	126.94 (15)	C9—C8—C7	122.11 (13)
N1—C2—C4	118.44 (14)	C10—C9—C8	123.02 (14)
C2—C3—S1	111.37 (12)	C10—C9—Cl1	118.29 (12)
C2—C3—H3A	124.3	C8—C9—Cl1	118.69 (11)
S1—C3—H3A	124.3	C11—C10—C9	118.91 (15)
C2—C4—H4A	109.5	C11—C10—H10	120.5
C2—C4—H4B	109.5	C9—C10—H10	120.5
H4A—C4—H4B	109.5	C10—C11—C12	120.41 (15)
C2—C4—H4C	109.5	C10—C11—H11	119.8
H4A—C4—H4C	109.5	C12—C11—H11	119.8
H4B—C4—H4C	109.5	C11—C12—C13	118.67 (14)
O1—C5—N2	122.92 (15)	C11—C12—H12	120.7
O1—C5—C6	122.55 (14)	C13—C12—H12	120.7
N2—C5—C6	114.51 (13)	C12—C13—C8	123.46 (14)
N3—C6—C5	113.47 (13)	C12—C13—Cl2	117.64 (12)
N3—C6—H6A	108.9	C8—C13—Cl2	118.89 (11)
C2—N1—C1—N2	−179.90 (14)	N3—C7—C8—C13	−91.91 (15)
C2—N1—C1—S1	0.25 (17)	N3—C7—C8—C9	86.22 (17)
C5—N2—C1—N1	176.97 (15)	C13—C8—C9—C10	−0.6 (2)
C5—N2—C1—S1	−3.2 (2)	C7—C8—C9—C10	−178.88 (14)
C3—S1—C1—N1	0.33 (13)	C13—C8—C9—Cl1	179.82 (11)
C3—S1—C1—N2	−179.52 (14)	C7—C8—C9—Cl1	1.57 (19)
C1—N1—C2—C3	−0.9 (2)	C8—C9—C10—C11	0.3 (2)
C1—N1—C2—C4	177.06 (14)	Cl1—C9—C10—C11	179.80 (12)
N1—C2—C3—S1	1.16 (19)	C9—C10—C11—C12	0.1 (2)
C4—C2—C3—S1	−176.61 (15)	C10—C11—C12—C13	0.1 (2)
C1—S1—C3—C2	−0.81 (13)	C11—C12—C13—C8	−0.5 (2)
C1—N2—C5—O1	1.8 (3)	C11—C12—C13—Cl2	−179.61 (12)
C1—N2—C5—C6	−179.27 (14)	C9—C8—C13—C12	0.8 (2)
C7—N3—C6—C5	90.42 (15)	C7—C8—C13—C12	179.01 (14)
O1—C5—C6—N3	−169.05 (15)	C9—C8—C13—Cl2	179.86 (11)
N2—C5—C6—N3	12.0 (2)	C7—C8—C13—Cl2	−1.90 (19)
C6—N3—C7—C8	174.04 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N1i	0.89 (2)	2.32 (2)	3.130 (2)	150.9 (17)
C7—H7B···O1ii	0.99	2.53	3.3233 (19)	137
N2—H2···N3	0.84 (2)	2.26 (2)	2.6742 (19)	111 (2)
Cg1—···.Cg1ii	.	.	3.665 (2)	.
Cg1—···.Cg2iii	.	.	3.766 (3)	.
Cg2—···.Cg2iv	.	.	3.507 (3)	.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N1i	0.89 (2)	2.32 (2)	3.130 (2)	150.9 (17)
C7—H7B⋯O1ii	0.99	2.53	3.3233 (19)	137
N2—H2⋯N3	0.84 (2)	2.26 (2)	2.6742 (19)	111 (2)

Symmetry codes: (i) ; (ii) .