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

In the title compound, C(23)H(23)N(5)S, the thia-zole ring and pyrimidine ring are almost coplanar, making a dihedral angle of 4.02 (9)°. in the crystal, weak inter-molecular N-H⋯N inter-actions 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 = 401.52

Triclinic,

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[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.145

S = 1.04

4535 reflections

267 parameters

H-atom parameters constrained

Δρmax = 0.88 e Å−3

Δρmin = −0.29 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/S1600536810053560/ng5078sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053560/ng5078Isup2.hkl

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

C23H23N5S	Z = 2
Mr = 401.52	F(000) = 424
Triclinic, P1	Dx = 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

Rigaku FC10/Saturn724+ diffractometer	4535 independent reflections
Radiation source: fine-focus sealed tube	3652 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.2°
phi and ω scans	h = −9→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008)	k = −12→12
Tmin = 0.910, Tmax = 0.973	l = −17→17
9716 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0846P)2 + 0.3916P] where P = (Fo2 + 2Fc2)/3
4535 reflections	(Δ/σ)max = 0.028
267 parameters	Δρmax = 0.88 e Å−3
0 restraints	Δρmin = −0.29 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
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)*

	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)

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)

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

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) .