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

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

doi:10.1107/S1600536810053560

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o259

doi:10.1107/S1600536810053560

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

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

^aZhejiang Pharmaceutical College, Ningbo 315100, People's Republic of China, ^bCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310032, People's Republic of China, ^cTaizhou Vocational & Technical College, Taizhou 318000, People's Republic of China, and ^dNantong Center for Disease Control and Prevention, Nantong 226007, People's Republic of China

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

In the title compound, C₂₃H₂₃N₅S, the thiazole ring and pyrimidine ring are almost coplanar, making a dihedral angle of 4.02 (9)°. in the crystal, weak intermolecular N—H⋯N interactions 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

C₂₃H₂₃N₅S
M_r = 401.52
Triclinic, $[P \overline 1]$
a = 7.886 (2) Å
b = 9.576 (3) Å
c = 13.531 (4) Å
α = 86.590 (9)°
β = 81.657 (7)°
γ = 85.926 (8)°
V = 1007.2 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 103 K
0.53 × 0.37 × 0.15 mm

Data collection

Rigaku FC10/Saturn724+ diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008 ) T_min = 0.910, T_max = 0.973
9716 measured reflections
4535 independent reflections
3652 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.145
S = 1.04
4535 reflections
267 parameters
H-atom parameters constrained
Δρ_max = 0.88 e Å⁻³
Δρ_min = −0.29 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	2.22	3.097 (2)	173
Symmetry code: (i) -x+1, -y, -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/S1600536810053560/ng5078sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810053560/ng5078Isup2.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 4.02 (9)°. The aniline rings (C1/C2/C3/C4/C5/C6/N1) and (C14/C15/C16/C17/C18/C19/N5) make dihedral angles of 80.96 (11) Å and 14.15 (9) Å with the thiazole ring, respectively. In the thiazole ring, the bond lengths S1—C7 [1.739 (2) Å], S1—C9 [1.748 (18) Å] and N2—C8 [1.372 (2) Å] correspond to typical single bond, and the C7—N2 [1.312 (2) Å], C8—C9 [1.373 (3) 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-[4-methyl-2-(methyl-o-tolyl-amino)-thiazol-5-yl]-propenone (1.575 g, 5 mmol) and NaOH (0.2 g, 5 mmol) in 2-methoxylethanol (20 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 11 h. After concentration, the residue was filtered and washed liberally with ethanol and water. Recrystallization from acetone affored the title compound as dark yellow crystals, 1.17 g, m.p.455–458 K, yield 58.5%. 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.): 8.24 (d, 1H, J = 5.2 Hz, py—H), 7.65 (s, 1H, Ar—H), 7.36–7.27 (m, 4H, Ar—H), 7.13–7.09 (m, 2H, Ar—H), 6.92 (s, 1H, Ar—H), 6.79 (d, 1H, J = 5.6 Hz, py—H), 3.49 (s, 3H, CH₃), 2.61 (s, 3H, CH₃), 2.29 (s, 3H, CH₃), 2.15 (s, 3H, CH₃). EIMS m/z (%): 401 (M⁺, 100), 386 (28), 368 (17), 283 (9), 222 (8), 129 (10), 118 (8), 98 (11), 91 (15), 83 (12), 73 (21), 65 (10), 57 (28).

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

Crystal data top

C₂₃H₂₃N₅S	Z = 2
M_r = 401.52	F(000) = 424
Triclinic, P1	D_x = 1.324 Mg m⁻³
Hall symbol: -P 1	Melting point = 455–458 K
a = 7.886 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.576 (3) Å	Cell parameters from 2962 reflections
c = 13.531 (4) Å	θ = 3.1–27.5°
α = 86.590 (9)°	µ = 0.18 mm⁻¹
β = 81.657 (7)°	T = 103 K
γ = 85.926 (8)°	Chunk, yellow
V = 1007.2 (5) Å³	0.53 × 0.37 × 0.15 mm

Data collection top

Rigaku FC10/Saturn724+ diffractometer	4535 independent reflections
Radiation source: fine-focus sealed tube	3652 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
phi and ω scans	h = −9→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008)	k = −12→12
T_min = 0.910, T_max = 0.973	l = −17→17
9716 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0846P)² + 0.3916P] where P = (F_o² + 2F_c²)/3
4535 reflections	(Δ/σ)_max = 0.028
267 parameters	Δρ_max = 0.88 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₃H₂₃N₅S	γ = 85.926 (8)°
M_r = 401.52	V = 1007.2 (5) Å³
Triclinic, P1	Z = 2
a = 7.886 (2) Å	Mo Kα radiation
b = 9.576 (3) Å	µ = 0.18 mm⁻¹
c = 13.531 (4) Å	T = 103 K
α = 86.590 (9)°	0.53 × 0.37 × 0.15 mm
β = 81.657 (7)°

Data collection top

Rigaku FC10/Saturn724+ diffractometer	4535 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008)	3652 reflections with I > 2σ(I)
T_min = 0.910, T_max = 0.973	R_int = 0.025
9716 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.04	Δρ_max = 0.88 e Å⁻³
4535 reflections	Δρ_min = −0.29 e Å⁻³
267 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
S1	0.49286 (6)	0.59975 (5)	0.26125 (4)	0.02216 (15)
N1	0.5218 (2)	0.85391 (18)	0.16596 (14)	0.0291 (4)
N2	0.7115 (2)	0.78346 (17)	0.28067 (13)	0.0240 (4)
N3	0.5942 (2)	0.16585 (16)	0.49627 (12)	0.0200 (3)
N4	0.5120 (2)	0.34459 (16)	0.37770 (12)	0.0187 (3)
C1	0.4171 (3)	0.7392 (2)	0.03246 (17)	0.0313 (5)
C2	0.2762 (3)	0.7123 (2)	−0.01462 (18)	0.0389 (6)
H2	0.2943	0.6545	−0.0704	0.047*
C3	0.1159 (4)	0.7658 (3)	0.0169 (2)	0.0467 (7)
H3	0.0237	0.7459	−0.0171	0.056*
C4	0.0846 (4)	0.8502 (4)	0.0990 (2)	0.0548 (8)
H4	−0.0285	0.8877	0.1209	0.066*
C5	0.2161 (4)	0.8783 (3)	0.14753 (19)	0.0430 (6)
H5	0.1960	0.9358	0.2034	0.052*
C6	0.3856 (3)	0.8205 (2)	0.11364 (17)	0.0313 (5)
C7	0.5837 (3)	0.7599 (2)	0.23286 (15)	0.0224 (4)
C8	0.7434 (3)	0.6704 (2)	0.34395 (15)	0.0214 (4)
C9	0.6390 (2)	0.56111 (19)	0.34608 (14)	0.0189 (4)
C10	0.6291 (2)	0.42802 (19)	0.40239 (14)	0.0179 (4)
C11	0.7270 (3)	0.3854 (2)	0.47785 (14)	0.0217 (4)
H11	0.8053	0.4448	0.4987	0.026*
C12	0.7046 (3)	0.2525 (2)	0.52081 (15)	0.0225 (4)
H12	0.7723	0.2206	0.5713	0.027*
C13	0.4981 (2)	0.22012 (19)	0.42660 (14)	0.0187 (4)
C14	0.2321 (2)	0.16692 (19)	0.35740 (14)	0.0189 (4)
C15	0.1008 (2)	0.0738 (2)	0.37477 (14)	0.0206 (4)
H15	0.1113	−0.0060	0.4192	0.025*
C16	−0.0438 (3)	0.0964 (2)	0.32809 (15)	0.0232 (4)
H16	−0.1304	0.0310	0.3394	0.028*
C17	−0.0636 (3)	0.2142 (2)	0.26472 (15)	0.0224 (4)
H17	−0.1636	0.2293	0.2330	0.027*
C18	0.0630 (3)	0.3100 (2)	0.24782 (14)	0.0208 (4)
C19	0.2116 (3)	0.2851 (2)	0.29292 (14)	0.0212 (4)
H19	0.2997	0.3491	0.2797	0.025*
C20	0.5933 (3)	0.6860 (3)	−0.0052 (2)	0.0422 (6)
H20A	0.6656	0.7651	−0.0242	0.063*
H20B	0.5914	0.6309	−0.0637	0.063*
H20C	0.6400	0.6267	0.0473	0.063*
C21	0.5830 (3)	0.9947 (2)	0.15159 (19)	0.0368 (6)
H21A	0.6440	1.0133	0.2071	0.044*
H21B	0.4851	1.0633	0.1495	0.044*
H21C	0.6612	1.0023	0.0885	0.044*
C22	0.8931 (3)	0.6763 (2)	0.40003 (19)	0.0328 (5)
H22A	0.9559	0.7594	0.3763	0.039*
H22B	0.9697	0.5919	0.3888	0.039*
H22C	0.8516	0.6816	0.4717	0.039*
C23	0.0426 (3)	0.4413 (2)	0.18208 (16)	0.0257 (4)
H23A	0.1144	0.5124	0.2003	0.031*
H23B	−0.0780	0.4770	0.1913	0.031*
H23C	0.0781	0.4197	0.1119	0.031*
N5	0.3751 (2)	0.13476 (17)	0.40750 (13)	0.0220 (4)
H5N	0.3877	0.0470	0.4300	0.054 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0269 (3)	0.0208 (3)	0.0217 (3)	−0.00942 (19)	−0.01263 (19)	0.00710 (18)
N1	0.0400 (11)	0.0213 (8)	0.0299 (10)	−0.0104 (8)	−0.0187 (8)	0.0105 (7)
N2	0.0274 (9)	0.0211 (8)	0.0258 (9)	−0.0085 (7)	−0.0101 (7)	0.0045 (7)
N3	0.0207 (8)	0.0191 (8)	0.0211 (8)	−0.0012 (6)	−0.0070 (6)	0.0029 (6)
N4	0.0191 (8)	0.0181 (8)	0.0196 (8)	−0.0038 (6)	−0.0052 (6)	0.0015 (6)
C1	0.0364 (12)	0.0273 (11)	0.0297 (11)	−0.0028 (10)	−0.0069 (9)	0.0078 (9)
C2	0.0550 (16)	0.0320 (12)	0.0347 (13)	−0.0160 (11)	−0.0228 (11)	0.0133 (10)
C3	0.0469 (16)	0.0523 (16)	0.0453 (15)	−0.0117 (13)	−0.0219 (12)	0.0092 (12)
C4	0.0339 (14)	0.077 (2)	0.0510 (17)	0.0081 (14)	−0.0049 (12)	0.0043 (15)
C5	0.0512 (16)	0.0468 (15)	0.0304 (12)	0.0032 (12)	−0.0068 (11)	−0.0027 (11)
C6	0.0407 (13)	0.0279 (11)	0.0280 (11)	−0.0113 (10)	−0.0151 (9)	0.0115 (9)
C7	0.0269 (10)	0.0197 (9)	0.0218 (10)	−0.0073 (8)	−0.0070 (8)	0.0047 (7)
C8	0.0203 (9)	0.0218 (9)	0.0235 (10)	−0.0040 (8)	−0.0071 (7)	0.0000 (8)
C9	0.0202 (9)	0.0191 (9)	0.0186 (9)	−0.0026 (7)	−0.0076 (7)	0.0024 (7)
C10	0.0171 (9)	0.0173 (9)	0.0198 (9)	−0.0013 (7)	−0.0041 (7)	−0.0005 (7)
C11	0.0221 (10)	0.0215 (9)	0.0237 (10)	−0.0047 (8)	−0.0097 (8)	0.0017 (8)
C12	0.0240 (10)	0.0217 (9)	0.0235 (10)	−0.0004 (8)	−0.0104 (8)	0.0000 (8)
C13	0.0184 (9)	0.0191 (9)	0.0189 (9)	−0.0018 (7)	−0.0040 (7)	0.0001 (7)
C14	0.0200 (9)	0.0190 (9)	0.0182 (9)	−0.0017 (7)	−0.0048 (7)	0.0001 (7)
C15	0.0228 (10)	0.0177 (9)	0.0214 (9)	−0.0035 (8)	−0.0027 (7)	0.0006 (7)
C16	0.0187 (9)	0.0244 (10)	0.0264 (10)	−0.0046 (8)	−0.0013 (8)	−0.0028 (8)
C17	0.0184 (9)	0.0271 (10)	0.0224 (10)	−0.0019 (8)	−0.0048 (7)	−0.0027 (8)
C18	0.0229 (10)	0.0231 (9)	0.0167 (9)	−0.0008 (8)	−0.0043 (7)	−0.0015 (7)
C19	0.0223 (10)	0.0218 (9)	0.0208 (9)	−0.0066 (8)	−0.0065 (7)	0.0023 (7)
C20	0.0405 (14)	0.0417 (14)	0.0422 (14)	0.0058 (11)	−0.0077 (11)	0.0114 (11)
C21	0.0498 (15)	0.0227 (11)	0.0422 (14)	−0.0134 (10)	−0.0211 (11)	0.0123 (9)
C22	0.0306 (12)	0.0280 (11)	0.0449 (13)	−0.0136 (9)	−0.0218 (10)	0.0096 (10)
C23	0.0269 (10)	0.0263 (10)	0.0252 (10)	−0.0027 (8)	−0.0098 (8)	0.0038 (8)
N5	0.0235 (9)	0.0177 (8)	0.0270 (9)	−0.0053 (7)	−0.0116 (7)	0.0064 (6)

Geometric parameters (Å, º) top

S1—C7	1.738 (2)	C12—H12	0.9500
S1—C9	1.7478 (18)	C13—N5	1.373 (2)
N1—C7	1.356 (2)	C14—C15	1.400 (3)
N1—C6	1.433 (3)	C14—C19	1.402 (3)
N1—C21	1.457 (3)	C14—N5	1.405 (2)
N2—C7	1.313 (2)	C15—C16	1.380 (3)
N2—C8	1.372 (2)	C15—H15	0.9500
N3—C12	1.332 (2)	C16—C17	1.390 (3)
N3—C13	1.351 (2)	C16—H16	0.9500
N4—C13	1.332 (2)	C17—C18	1.388 (3)
N4—C10	1.352 (2)	C17—H17	0.9500
C1—C6	1.367 (3)	C18—C19	1.397 (3)
C1—C2	1.405 (3)	C18—C23	1.509 (3)
C1—C20	1.475 (3)	C19—H19	0.9500
C2—C3	1.349 (4)	C20—H20A	0.9800
C2—H2	0.9500	C20—H20B	0.9800
C3—C4	1.396 (4)	C20—H20C	0.9800
C3—H3	0.9500	C21—H21A	0.9800
C4—C5	1.355 (4)	C21—H21B	0.9800
C4—H4	0.9500	C21—H21C	0.9800
C5—C6	1.432 (4)	C22—H22A	0.9800
C5—H5	0.9500	C22—H22B	0.9800
C8—C9	1.374 (3)	C22—H22C	0.9800
C8—C22	1.499 (3)	C23—H23A	0.9800
C9—C10	1.447 (3)	C23—H23B	0.9800
C10—C11	1.393 (2)	C23—H23C	0.9800
C11—C12	1.380 (3)	N5—H5N	0.8800
C11—H11	0.9500

C7—S1—C9	88.26 (9)	C15—C14—C19	118.35 (17)
C7—N1—C6	120.68 (17)	C15—C14—N5	116.79 (17)
C7—N1—C21	120.59 (17)	C19—C14—N5	124.86 (17)
C6—N1—C21	118.57 (16)	C16—C15—C14	120.77 (18)
C7—N2—C8	109.74 (16)	C16—C15—H15	119.6
C12—N3—C13	114.47 (16)	C14—C15—H15	119.6
C13—N4—C10	117.30 (16)	C15—C16—C17	120.50 (18)
C6—C1—C2	117.4 (2)	C15—C16—H16	119.8
C6—C1—C20	120.8 (2)	C17—C16—H16	119.8
C2—C1—C20	121.8 (2)	C18—C17—C16	119.96 (18)
C3—C2—C1	122.0 (3)	C18—C17—H17	120.0
C3—C2—H2	119.0	C16—C17—H17	120.0
C1—C2—H2	119.0	C17—C18—C19	119.56 (18)
C2—C3—C4	120.4 (2)	C17—C18—C23	121.20 (17)
C2—C3—H3	119.8	C19—C18—C23	119.23 (18)
C4—C3—H3	119.8	C18—C19—C14	120.82 (18)
C5—C4—C3	119.8 (3)	C18—C19—H19	119.6
C5—C4—H4	120.1	C14—C19—H19	119.6
C3—C4—H4	120.1	C1—C20—H20A	109.5
C4—C5—C6	119.3 (2)	C1—C20—H20B	109.5
C4—C5—H5	120.3	H20A—C20—H20B	109.5
C6—C5—H5	120.3	C1—C20—H20C	109.5
C1—C6—C5	121.1 (2)	H20A—C20—H20C	109.5
C1—C6—N1	121.1 (2)	H20B—C20—H20C	109.5
C5—C6—N1	117.8 (2)	N1—C21—H21A	109.5
N2—C7—N1	123.19 (18)	N1—C21—H21B	109.5
N2—C7—S1	116.16 (14)	H21A—C21—H21B	109.5
N1—C7—S1	120.64 (15)	N1—C21—H21C	109.5
N2—C8—C9	116.43 (17)	H21A—C21—H21C	109.5
N2—C8—C22	116.68 (17)	H21B—C21—H21C	109.5
C9—C8—C22	126.83 (18)	C8—C22—H22A	109.5
C8—C9—C10	133.18 (17)	C8—C22—H22B	109.5
C8—C9—S1	109.40 (14)	H22A—C22—H22B	109.5
C10—C9—S1	117.43 (14)	C8—C22—H22C	109.5
N4—C10—C11	120.64 (17)	H22A—C22—H22C	109.5
N4—C10—C9	114.62 (16)	H22B—C22—H22C	109.5
C11—C10—C9	124.73 (17)	C18—C23—H23A	109.5
C12—C11—C10	116.55 (18)	C18—C23—H23B	109.5
C12—C11—H11	121.7	H23A—C23—H23B	109.5
C10—C11—H11	121.7	C18—C23—H23C	109.5
N3—C12—C11	124.37 (17)	H23A—C23—H23C	109.5
N3—C12—H12	117.8	H23B—C23—H23C	109.5
C11—C12—H12	117.8	C13—N5—C14	129.50 (16)
N4—C13—N3	126.49 (17)	C13—N5—H5N	115.3
N4—C13—N5	119.31 (16)	C14—N5—H5N	115.3
N3—C13—N5	114.20 (16)

C6—C1—C2—C3	1.2 (3)	C7—S1—C9—C10	179.10 (16)
C20—C1—C2—C3	−177.0 (2)	C13—N4—C10—C11	−1.6 (3)
C1—C2—C3—C4	−0.5 (4)	C13—N4—C10—C9	179.50 (16)
C2—C3—C4—C5	−0.1 (4)	C8—C9—C10—N4	−176.2 (2)
C3—C4—C5—C6	−0.1 (4)	S1—C9—C10—N4	3.7 (2)
C2—C1—C6—C5	−1.4 (3)	C8—C9—C10—C11	5.0 (4)
C20—C1—C6—C5	176.9 (2)	S1—C9—C10—C11	−175.12 (16)
C2—C1—C6—N1	−179.71 (18)	N4—C10—C11—C12	3.5 (3)
C20—C1—C6—N1	−1.4 (3)	C9—C10—C11—C12	−177.68 (18)
C4—C5—C6—C1	0.9 (4)	C13—N3—C12—C11	−2.2 (3)
C4—C5—C6—N1	179.3 (2)	C10—C11—C12—N3	−1.5 (3)
C7—N1—C6—C1	−79.6 (3)	C10—N4—C13—N3	−2.7 (3)
C21—N1—C6—C1	105.1 (3)	C10—N4—C13—N5	176.82 (18)
C7—N1—C6—C5	102.0 (3)	C12—N3—C13—N4	4.6 (3)
C21—N1—C6—C5	−73.3 (3)	C12—N3—C13—N5	−175.00 (17)
C8—N2—C7—N1	179.19 (19)	C19—C14—C15—C16	1.2 (3)
C8—N2—C7—S1	0.2 (2)	N5—C14—C15—C16	−179.46 (18)
C6—N1—C7—N2	178.0 (2)	C14—C15—C16—C17	−1.6 (3)
C21—N1—C7—N2	−6.9 (3)	C15—C16—C17—C18	0.2 (3)
C6—N1—C7—S1	−3.0 (3)	C16—C17—C18—C19	1.6 (3)
C21—N1—C7—S1	172.13 (18)	C16—C17—C18—C23	−177.98 (18)
C9—S1—C7—N2	0.49 (18)	C17—C18—C19—C14	−1.9 (3)
C9—S1—C7—N1	−178.57 (19)	C23—C18—C19—C14	177.62 (18)
C7—N2—C8—C9	−1.0 (3)	C15—C14—C19—C18	0.6 (3)
C7—N2—C8—C22	176.42 (19)	N5—C14—C19—C18	−178.72 (18)
N2—C8—C9—C10	−178.7 (2)	N4—C13—N5—C14	−14.5 (3)
C22—C8—C9—C10	4.1 (4)	N3—C13—N5—C14	165.06 (19)
N2—C8—C9—S1	1.3 (2)	C15—C14—N5—C13	−160.93 (19)
C22—C8—C9—S1	−175.77 (19)	C19—C14—N5—C13	18.4 (3)
C7—S1—C9—C8	−0.97 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···N3ⁱ	0.88	2.22	3.097 (2)	173

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₃N₅S
M_r	401.52
Crystal system, space group	Triclinic, P1
Temperature (K)	103
a, b, c (Å)	7.886 (2), 9.576 (3), 13.531 (4)
α, β, γ (°)	86.590 (9), 81.657 (7), 85.926 (8)
V (Å³)	1007.2 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.53 × 0.37 × 0.15

Data collection
Diffractometer	Rigaku FC10/Saturn724+ diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2008)
T_min, T_max	0.910, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	9716, 4535, 3652
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.145, 1.04
No. of reflections	4535
No. of parameters	267
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.88, −0.29

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	2.22	3.097 (2)	173

Symmetry code: (i) −x+1, −y, −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 o259

doi:10.1107/S1600536810053560

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

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