4-{2-[(3,4-Dichloro­phen­yl)(meth­yl)amino]-4-methyl-1,3-thia­zol-5-yl}-N-(3-methyl­phen­yl)pyrimidin-2-amine

Li, H.-B.; Shi, H.-B.; Hu, W.-X.

doi:10.1107/S1600536810053547

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o260

doi:10.1107/S1600536810053547

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4-{2-[(3,4-Dichlorophenyl)(methyl)amino]-4-methyl-1,3-thiazol-5-yl}-N-(3-methylphenyl)pyrimidin-2-amine

Hai-Bo Li,^a Hai-Bo Shi ^b,^c and Wei-Xiao Hu ^c

^aNantong Center for Disease Control and Prevention, Nantong 226007, People's Republic of China, ^bZhejiang Pharmaceutical College, Ningbo 315100, People's Republic of China, and ^cCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310032, People's Republic of China

(Received 29 November 2010; accepted 21 December 2010; online 8 January 2011)

In the title compound, C₂₂H₁₉Cl₂N₅S, the thiazole 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_r = 456.38
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.033
wR(F²) = 0.091
S = 1.05
4626 reflections
275 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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) -x+1, -y+2, -z+1.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Thiazole derivatives are found to be associated with various biological activities (Narayana et al., 2004). In order to further study the structure-activity relationship (SAR) of the thiazolyl-pyrimidine derivatives, we introduced arylamino group into 2-position of thiazole ring of thiazolyl-pyrimidine according to the general pyrimidine condensation method of Bredereck (Bredereck et al., 1964). But, it was found that the obtained compound was not desired compound that confirmed by ¹H NMR, MS. So, the structure of (I) was further determined using single-crystal X-ray diffraction.

The molecular structure of (I) is illustrated in Fig. 1. The thiazole ring (S1/C7/N2/C8/C9) and the pyrimidine ring (C10/C11/C12/N3/C13/N4) are almost planar, with a dihedral angle of 6.48 (7)°. The aniline rings (C1/C2/C3/C4/C5/C6/N1) and (C14/C15/C16/C17/C18/C19/N5) make dihedral angles of 73.76 (8) Å and 14.16 (7) Å with the thiazole ring, respectively. In the thiazole ring, the bond lengths S1—C7 [1.739 (15) Å], S1—C9 [1.749 (15) Å] and N2—C8 [1.377 (19) Å] correspond to typical single bond, and the C7—N2 [1.310 (2) Å], C8—C9 [1.372 (2) Å] belong to typical for double bonds. The crystal structure is stabilized by intermolecular weak N—H···N interactions (Fig. 2). Furthermore, every two molecules containing two N—H···N hydrogen bondings consists a dimer as octagon.

Related literature top

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 top

A mixture of

3-dimethylamino-1-{2-[(3,4-Dichloro-phenyl)-methyl-amino]-4-methyl-thiazol-5-yl}-propenone (1.85 g, 5 mmol) and NaOH (0.2 g, 5 mmol) in 2-methoxylethanol (40 ml) was treated with N-m-tolyl-guanidine carbonate (1.58 g, 7.5 mmol). The reaction mixture was heated at 383 K under N₂ for 21 h. After concentration, the residue was filtered and washed liberally with ethanol and water. Recrystallization from THF affored the title compound as dark-brown crystals, 0.34 g, m.p.472–473 K, yield 15.0%. Since the crystal product was not found to be suitable for X-ray diffraction studies, a few crystals were dissolved in 2-butanone, which was allowed to evaporate slowly to give yellow crystals of (I) suitable for X-ray diffraction studies. ¹H NMR(CDCl₃, TMS, 400 MHz, δp.p.m.): 8.30 (d, 1H, J =5.2 Hz, py—H), 7.61 (s, 1H, Ar—H), 7.57 (d, 1H, J = 2.8 Hz, Ar—H), 7.51 (d, 1H, J = 8.8 Hz, Ar—H), 7.33 (dd, 1H, J₁= 2.4 Hz, J₂= 2.4 Hz, Ar—H), 7.23–7.15 (m, 2H, Ar—H), 7.04 (s, 1H, Ar—H), 6.84 (d, 1H, J = 5.6 Hz, py—H), 3.54 (s, 3H, CH₃), 2.59 (s, 3H, CH₃), 2.27 (s, 3H, CH₃). EIMS m/z (%): 455 (M⁺, 100), 440 (9), 295 (11), 256 (12), 222 (13), 213 (9), 185 (10),171 (8), 129 (19), 111 (9), 97 (16), 85 (19), 73 (41), 65 (8), 57 (48).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2008); cell refinement: CrystalClear (Rigaku/MSC, 2008); data reduction: CrystalClear (Rigaku/MSC, 2008); 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).

Figures top

	Fig. 1. The structure of (I), shown with 30% probability displacement ellipsoids.
	Fig. 2. Packing of the molecules down a axis. Dashed lines denote intermolecular N—H···N hydrogen bonds.

4-{2-[(3,4-Dichlorophenyl)(methyl)amino]-4-methyl-1,3-thiazol-5-yl}- N-(3-methylphenyl)pyrimidin-2-amine top

Crystal data top

C₂₂H₁₉Cl₂N₅S	Z = 2
M_r = 456.38	F(000) = 472
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0486P)² + 0.1912P] where P = (F_o² + 2F_c²)/3
4626 reflections	(Δ/σ)_max = 0.002
275 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₂H₁₉Cl₂N₅S	γ = 86.002 (6)°
M_r = 456.38	V = 1028.4 (3) Å³
Triclinic, P1	Z = 2
a = 7.9679 (15) Å	Mo Kα radiation
b = 9.4042 (19) Å	µ = 0.44 mm⁻¹
c = 14.166 (3) Å	T = 103 K
α = 85.421 (6)°	0.53 × 0.50 × 0.40 mm
β = 76.727 (5)°

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	4626 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008)	3906 reflections with I > 2σ(I)
T_min = 0.801, T_max = 0.844	R_int = 0.021
9828 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.05	Δρ_max = 0.37 e Å⁻³
4626 reflections	Δρ_min = −0.25 e Å⁻³
275 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₉Cl₂N₅S
M_r	456.38
Crystal system, space group	Triclinic, P1
Temperature (K)	103
a, b, c (Å)	7.9679 (15), 9.4042 (19), 14.166 (3)
α, β, γ (°)	85.421 (6), 76.727 (5), 86.002 (6)
V (Å³)	1028.4 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.53 × 0.50 × 0.40

Data collection
Diffractometer	Rigaku AFC10/Saturn724+ diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2008)
T_min, T_max	0.801, 0.844
No. of measured, independent and observed [I > 2σ(I)] reflections	9828, 4626, 3906
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.091, 1.05
No. of reflections	4626
No. of parameters	275
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.25

Computer programs: CrystalClear (Rigaku/MSC, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z+1.

Acknowledgements

We are very thankful to the Natural Science Foundation of Ningbo City (grant No. 2009 A610185) for financial support. We are also grateful to the Beijing Institute of Technology for the X-ray diffraction measurements.

References

Bredereck, H., Effenberger, F. & Botsch, H. (1964). Chem. Ber. 97, 3397–3406. CrossRef CAS Web of Science Google Scholar
Narayana, B., Raj, K. K. V., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2004). Eur. J. Med. Chem. 39, 867–872. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku/MSC (2008). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 2| February 2011| Page o260

doi:10.1107/S1600536810053547

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-{2-[(3,4-Di­chloro­phen­yl)(meth­yl)amino]-4-methyl-1,3-thia­zol-5-yl}-N-(3-methyl­phen­yl)pyrimidin-2-amine

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-{2-[(3,4-Dichlorophenyl)(methyl)amino]-4-methyl-1,3-thiazol-5-yl}-N-(3-methylphenyl)pyrimidin-2-amine