4-{2-[(3,4-Dichloro-phen-yl)(meth-yl)amino]-4-methyl-1,3-thia-zol-5-yl}-N-(3-methyl-phen-yl)pyrimidin-2-amine.

In the title compound, C(22)H(19)Cl(2)N(5)S, the thia-zole and pyrimidine rings are almost co-planar, making a dihedral angle of 6.48 (7)°. In the crystal, intermolecular N-H⋯N hydrogen bonds link pairs of molecules into centrosymmetric dimers..

Related literature

For general background to the biological activity of thia­zole derivatives, see: Narayana et al. (2004 ▶). For the synthesis of the title compound, see: Bredereck et al. (1964 ▶).

Experimental

Crystal data

C22H19Cl2N5S

M = 456.38

Triclinic,

a = 7.9679 (15) Å

b = 9.4042 (19) Å

c = 14.166 (3) Å

α = 85.421 (6)°

β = 76.727 (5)°

γ = 86.002 (6)°

V = 1028.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.44 mm−1

T = 103 K

0.53 × 0.50 × 0.40 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008) ▶ T min = 0.801, T max = 0.844

9828 measured reflections

4626 independent reflections

3906 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.091

S = 1.05

4626 reflections

275 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2008 ▶); 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: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810053547/ng5079sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053547/ng5079Isup2.hkl

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

C22H19Cl2N5S	Z = 2
Mr = 456.38	F(000) = 472
Triclinic, P1	Dx = 1.474 Mg m−3
Hall symbol: -P 1	Melting point = 473–472 K
a = 7.9679 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4042 (19) Å	Cell parameters from 3163 reflections
c = 14.166 (3) Å	θ = 3.3–27.5°
α = 85.421 (6)°	µ = 0.44 mm−1
β = 76.727 (5)°	T = 103 K
γ = 86.002 (6)°	Block, yellow
V = 1028.4 (3) Å3	0.53 × 0.50 × 0.40 mm

Rigaku AFC10/Saturn724+ diffractometer	4626 independent reflections
Radiation source: fine-focus sealed tube	3906 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.3°
phi and ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008)	k = −12→12
Tmin = 0.801, Tmax = 0.844	l = −16→18
9828 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0486P)2 + 0.1912P] where P = (Fo2 + 2Fc2)/3
4626 reflections	(Δ/σ)max = 0.002
275 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.25 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.

	x	y	z	Uiso*/Ueq
Cl1	0.65348 (6)	0.39036 (4)	1.06940 (3)	0.02494 (11)
Cl2	1.02033 (6)	0.23777 (5)	0.99130 (3)	0.03270 (13)
S1	0.46927 (5)	0.38651 (4)	0.73411 (3)	0.01502 (10)
N1	0.42851 (17)	0.12266 (14)	0.82588 (10)	0.0177 (3)
N2	0.24614 (17)	0.20416 (14)	0.72255 (10)	0.0174 (3)
N3	0.40431 (17)	0.83042 (14)	0.50231 (10)	0.0166 (3)
N4	0.46548 (16)	0.64873 (13)	0.62050 (9)	0.0152 (3)
C1	0.5466 (2)	0.24613 (16)	0.93887 (11)	0.0167 (3)
H1	0.4370	0.2936	0.9610	0.020*
C2	0.6847 (2)	0.27394 (16)	0.97755 (11)	0.0172 (3)
C3	0.8457 (2)	0.20465 (18)	0.94480 (12)	0.0199 (3)
C4	0.8656 (2)	0.1063 (2)	0.87532 (13)	0.0260 (4)
H4	0.9749	0.0581	0.8535	0.031*
C5	0.7274 (2)	0.07723 (19)	0.83720 (12)	0.0227 (4)
H5	0.7415	0.0083	0.7901	0.027*
C6	0.5687 (2)	0.14890 (16)	0.86789 (11)	0.0158 (3)
C7	0.37223 (19)	0.22404 (16)	0.76455 (11)	0.0150 (3)
C8	0.2218 (2)	0.32085 (16)	0.66094 (11)	0.0161 (3)
C9	0.3305 (2)	0.42957 (16)	0.65541 (11)	0.0153 (3)
C10	0.3515 (2)	0.56427 (16)	0.59808 (11)	0.0144 (3)
C11	0.2660 (2)	0.60746 (16)	0.52437 (11)	0.0173 (3)
H11	0.1906	0.5473	0.5052	0.021*
C12	0.2970 (2)	0.74247 (17)	0.48071 (12)	0.0180 (3)
H12	0.2372	0.7750	0.4316	0.022*
C13	0.4895 (2)	0.77493 (16)	0.57055 (11)	0.0150 (3)
C14	0.7437 (2)	0.82794 (16)	0.63641 (11)	0.0155 (3)
C15	0.8818 (2)	0.91812 (16)	0.61470 (11)	0.0162 (3)
H15	0.8825	0.9958	0.5675	0.019*
C16	1.0172 (2)	0.89571 (16)	0.66104 (12)	0.0180 (3)
H16	1.1084	0.9595	0.6468	0.022*
C17	1.0204 (2)	0.78011 (17)	0.72849 (12)	0.0176 (3)
H17	1.1144	0.7642	0.7595	0.021*
C18	0.8856 (2)	0.68802 (17)	0.75029 (11)	0.0173 (3)
C19	0.7475 (2)	0.71314 (16)	0.70470 (11)	0.0179 (3)
H19	0.6546	0.6510	0.7205	0.021*
C20	0.3733 (2)	−0.02305 (17)	0.82886 (13)	0.0224 (4)
H20A	0.2555	−0.0291	0.8686	0.027*
H20B	0.4515	−0.0895	0.8573	0.027*
H20C	0.3759	−0.0482	0.7627	0.027*
C21	0.0762 (2)	0.31764 (18)	0.61070 (13)	0.0248 (4)
H21A	0.0086	0.4089	0.6166	0.030*
H21B	0.0020	0.2399	0.6408	0.030*
H21C	0.1229	0.3020	0.5418	0.030*
C22	0.8862 (2)	0.56045 (18)	0.82177 (13)	0.0243 (4)
H22A	0.8018	0.5787	0.8823	0.029*
H22B	1.0015	0.5437	0.8352	0.029*
H22C	0.8558	0.4761	0.7942	0.029*
N5	0.61031 (17)	0.86089 (14)	0.58696 (10)	0.0185 (3)
H5N	0.6034	0.9498	0.5630	0.032 (6)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0352 (2)	0.0191 (2)	0.0227 (2)	0.00067 (16)	−0.00980 (17)	−0.00635 (15)
Cl2	0.0238 (2)	0.0468 (3)	0.0331 (3)	−0.00328 (19)	−0.01516 (19)	−0.0099 (2)
S1	0.01644 (19)	0.01321 (18)	0.0177 (2)	−0.00395 (13)	−0.00857 (15)	0.00174 (14)
N1	0.0186 (7)	0.0134 (6)	0.0232 (7)	−0.0041 (5)	−0.0095 (6)	0.0033 (5)
N2	0.0165 (7)	0.0164 (7)	0.0209 (7)	−0.0034 (5)	−0.0075 (5)	0.0005 (5)
N3	0.0178 (7)	0.0153 (6)	0.0177 (7)	−0.0006 (5)	−0.0067 (5)	0.0004 (5)
N4	0.0166 (6)	0.0143 (6)	0.0163 (7)	−0.0020 (5)	−0.0068 (5)	−0.0005 (5)
C1	0.0175 (8)	0.0151 (7)	0.0167 (8)	0.0007 (6)	−0.0040 (6)	0.0021 (6)
C2	0.0249 (8)	0.0130 (7)	0.0140 (8)	−0.0015 (6)	−0.0057 (6)	0.0016 (6)
C3	0.0174 (8)	0.0255 (8)	0.0182 (8)	−0.0026 (6)	−0.0070 (6)	−0.0004 (6)
C4	0.0165 (8)	0.0362 (10)	0.0261 (10)	0.0036 (7)	−0.0055 (7)	−0.0100 (7)
C5	0.0197 (8)	0.0295 (9)	0.0201 (9)	0.0011 (7)	−0.0048 (7)	−0.0095 (7)
C6	0.0166 (7)	0.0159 (7)	0.0148 (8)	−0.0027 (6)	−0.0048 (6)	0.0043 (6)
C7	0.0149 (7)	0.0138 (7)	0.0161 (8)	−0.0026 (6)	−0.0028 (6)	−0.0007 (6)
C8	0.0158 (7)	0.0153 (7)	0.0186 (8)	−0.0011 (6)	−0.0066 (6)	−0.0016 (6)
C9	0.0155 (7)	0.0155 (7)	0.0167 (8)	−0.0001 (6)	−0.0073 (6)	−0.0018 (6)
C10	0.0160 (7)	0.0128 (7)	0.0156 (8)	0.0001 (5)	−0.0056 (6)	−0.0025 (6)
C11	0.0184 (8)	0.0172 (8)	0.0187 (8)	−0.0016 (6)	−0.0090 (6)	−0.0019 (6)
C12	0.0199 (8)	0.0181 (8)	0.0172 (8)	0.0020 (6)	−0.0078 (6)	−0.0004 (6)
C13	0.0169 (7)	0.0152 (7)	0.0129 (7)	−0.0004 (6)	−0.0034 (6)	−0.0011 (6)
C14	0.0164 (7)	0.0161 (7)	0.0145 (8)	−0.0023 (6)	−0.0042 (6)	−0.0019 (6)
C15	0.0184 (8)	0.0136 (7)	0.0151 (8)	−0.0020 (6)	−0.0008 (6)	−0.0001 (6)
C16	0.0145 (7)	0.0177 (8)	0.0210 (8)	−0.0034 (6)	−0.0005 (6)	−0.0042 (6)
C17	0.0156 (8)	0.0205 (8)	0.0180 (8)	−0.0001 (6)	−0.0056 (6)	−0.0050 (6)
C18	0.0210 (8)	0.0169 (7)	0.0152 (8)	−0.0014 (6)	−0.0062 (6)	−0.0014 (6)
C19	0.0208 (8)	0.0168 (8)	0.0179 (8)	−0.0068 (6)	−0.0072 (6)	0.0007 (6)
C20	0.0230 (9)	0.0149 (8)	0.0304 (10)	−0.0057 (6)	−0.0090 (7)	0.0055 (7)
C21	0.0248 (9)	0.0227 (9)	0.0321 (10)	−0.0076 (7)	−0.0168 (7)	0.0028 (7)
C22	0.0303 (9)	0.0217 (9)	0.0249 (9)	−0.0067 (7)	−0.0149 (7)	0.0051 (7)
N5	0.0228 (7)	0.0146 (7)	0.0203 (7)	−0.0053 (5)	−0.0101 (6)	0.0051 (5)

Cl1—C2	1.7304 (17)	C11—C12	1.380 (2)
Cl2—C3	1.7266 (17)	C11—H11	0.9500
S1—C7	1.7392 (15)	C12—H12	0.9500
S1—C9	1.7492 (15)	C13—N5	1.3694 (19)
N1—C7	1.361 (2)	C14—C19	1.394 (2)
N1—C6	1.424 (2)	C14—C15	1.399 (2)
N1—C20	1.4626 (19)	C14—N5	1.407 (2)
N2—C7	1.310 (2)	C15—C16	1.382 (2)
N2—C8	1.3778 (19)	C15—H15	0.9500
N3—C12	1.330 (2)	C16—C17	1.392 (2)
N3—C13	1.3561 (19)	C16—H16	0.9500
N4—C13	1.3346 (19)	C17—C18	1.391 (2)
N4—C10	1.3530 (19)	C17—H17	0.9500
C1—C2	1.386 (2)	C18—C19	1.396 (2)
C1—C6	1.386 (2)	C18—C22	1.507 (2)
C1—H1	0.9500	C19—H19	0.9500
C2—C3	1.394 (2)	C20—H20A	0.9800
C3—C4	1.380 (2)	C20—H20B	0.9800
C4—C5	1.384 (2)	C20—H20C	0.9800
C4—H4	0.9500	C21—H21A	0.9800
C5—C6	1.385 (2)	C21—H21B	0.9800
C5—H5	0.9500	C21—H21C	0.9800
C8—C9	1.372 (2)	C22—H22A	0.9800
C8—C21	1.497 (2)	C22—H22B	0.9800
C9—C10	1.447 (2)	C22—H22C	0.9800
C10—C11	1.392 (2)	N5—H5N	0.8800
C7—S1—C9	88.31 (7)	N4—C13—N3	126.28 (14)
C7—N1—C6	120.09 (13)	N4—C13—N5	119.49 (14)
C7—N1—C20	118.53 (13)	N3—C13—N5	114.23 (13)
C6—N1—C20	119.69 (12)	C19—C14—C15	118.38 (14)
C7—N2—C8	110.18 (13)	C19—C14—N5	124.83 (14)
C12—N3—C13	114.27 (13)	C15—C14—N5	116.80 (13)
C13—N4—C10	117.34 (13)	C16—C15—C14	120.89 (14)
C2—C1—C6	119.86 (15)	C16—C15—H15	119.6
C2—C1—H1	120.1	C14—C15—H15	119.6
C6—C1—H1	120.1	C15—C16—C17	120.25 (14)
C1—C2—C3	120.02 (15)	C15—C16—H16	119.9
C1—C2—Cl1	119.41 (12)	C17—C16—H16	119.9
C3—C2—Cl1	120.53 (13)	C18—C17—C16	119.82 (15)
C4—C3—C2	119.66 (15)	C18—C17—H17	120.1
C4—C3—Cl2	119.29 (13)	C16—C17—H17	120.1
C2—C3—Cl2	121.04 (13)	C17—C18—C19	119.58 (14)
C3—C4—C5	120.44 (16)	C17—C18—C22	121.23 (15)
C3—C4—H4	119.8	C19—C18—C22	119.20 (14)
C5—C4—H4	119.8	C14—C19—C18	121.06 (14)
C4—C5—C6	119.86 (16)	C14—C19—H19	119.5
C4—C5—H5	120.1	C18—C19—H19	119.5
C6—C5—H5	120.1	N1—C20—H20A	109.5
C5—C6—C1	120.11 (15)	N1—C20—H20B	109.5
C5—C6—N1	119.71 (15)	H20A—C20—H20B	109.5
C1—C6—N1	120.18 (14)	N1—C20—H20C	109.5
N2—C7—N1	122.48 (14)	H20A—C20—H20C	109.5
N2—C7—S1	115.90 (11)	H20B—C20—H20C	109.5
N1—C7—S1	121.59 (12)	C8—C21—H21A	109.5
C9—C8—N2	115.95 (14)	C8—C21—H21B	109.5
C9—C8—C21	127.26 (14)	H21A—C21—H21B	109.5
N2—C8—C21	116.74 (13)	C8—C21—H21C	109.5
C8—C9—C10	132.96 (14)	H21A—C21—H21C	109.5
C8—C9—S1	109.62 (11)	H21B—C21—H21C	109.5
C10—C9—S1	117.41 (11)	C18—C22—H22A	109.5
N4—C10—C11	120.73 (14)	C18—C22—H22B	109.5
N4—C10—C9	114.52 (13)	H22A—C22—H22B	109.5
C11—C10—C9	124.75 (14)	C18—C22—H22C	109.5
C12—C11—C10	116.32 (14)	H22A—C22—H22C	109.5
C12—C11—H11	121.8	H22B—C22—H22C	109.5
C10—C11—H11	121.8	C13—N5—C14	129.52 (13)
N3—C12—C11	124.83 (14)	C13—N5—H5N	115.2
N3—C12—H12	117.6	C14—N5—H5N	115.2
C11—C12—H12	117.6
C6—C1—C2—C3	0.3 (2)	C7—S1—C9—C8	1.59 (12)
C6—C1—C2—Cl1	−177.54 (11)	C7—S1—C9—C10	−177.37 (13)
C1—C2—C3—C4	−1.4 (2)	C13—N4—C10—C11	1.2 (2)
Cl1—C2—C3—C4	176.42 (13)	C13—N4—C10—C9	−179.55 (13)
C1—C2—C3—Cl2	179.72 (12)	C8—C9—C10—N4	174.45 (17)
Cl1—C2—C3—Cl2	−2.50 (19)	S1—C9—C10—N4	−6.89 (19)
C2—C3—C4—C5	0.8 (3)	C8—C9—C10—C11	−6.3 (3)
Cl2—C3—C4—C5	179.69 (14)	S1—C9—C10—C11	172.32 (13)
C3—C4—C5—C6	1.0 (3)	N4—C10—C11—C12	−3.6 (2)
C4—C5—C6—C1	−2.1 (2)	C9—C10—C11—C12	177.22 (15)
C4—C5—C6—N1	177.66 (15)	C13—N3—C12—C11	2.2 (2)
C2—C1—C6—C5	1.5 (2)	C10—C11—C12—N3	1.8 (2)
C2—C1—C6—N1	−178.28 (13)	C10—N4—C13—N3	3.5 (2)
C7—N1—C6—C5	−108.63 (18)	C10—N4—C13—N5	−176.52 (14)
C20—N1—C6—C5	56.3 (2)	C12—N3—C13—N4	−5.1 (2)
C7—N1—C6—C1	71.1 (2)	C12—N3—C13—N5	174.89 (14)
C20—N1—C6—C1	−123.93 (16)	C19—C14—C15—C16	−1.2 (2)
C8—N2—C7—N1	−177.07 (14)	N5—C14—C15—C16	178.77 (14)
C8—N2—C7—S1	0.87 (18)	C14—C15—C16—C17	1.7 (2)
C6—N1—C7—N2	178.64 (14)	C15—C16—C17—C18	−0.9 (2)
C20—N1—C7—N2	13.5 (2)	C16—C17—C18—C19	−0.5 (2)
C6—N1—C7—S1	0.8 (2)	C16—C17—C18—C22	179.02 (15)
C20—N1—C7—S1	−164.32 (12)	C15—C14—C19—C18	−0.2 (2)
C9—S1—C7—N2	−1.46 (13)	N5—C14—C19—C18	179.85 (15)
C9—S1—C7—N1	176.49 (14)	C17—C18—C19—C14	1.0 (2)
C7—N2—C8—C9	0.5 (2)	C22—C18—C19—C14	−178.47 (16)
C7—N2—C8—C21	−177.22 (14)	N4—C13—N5—C14	14.1 (2)
N2—C8—C9—C10	177.21 (16)	N3—C13—N5—C14	−165.88 (15)
C21—C8—C9—C10	−5.4 (3)	C19—C14—N5—C13	−21.4 (3)
N2—C8—C9—S1	−1.52 (18)	C15—C14—N5—C13	158.68 (16)
C21—C8—C9—S1	175.88 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···N3i	0.88	2.20	3.078 (2)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5N⋯N3i	0.88	2.20	3.078 (2)	177

Symmetry code: (i) .