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

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

doi:10.1107/S1600536810053559

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o261

doi:10.1107/S1600536810053559

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

Hai-Bo Shi,^a,^b Hai-Bo Li ^c 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, and ^cNantong 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)

The asymmetric unit of the title compound, C₂₃H₂₃N₅OS, contains two independent molecules. In one molecule, the thiazole and pyrimidine rings are almost co-planar, making a dihedral angle of 2.48 (8)°. In the other molecule, the corresponding dihedral angle is 12.82 (8)°. The crystal structure is stabilized by weak intermolecular N—H⋯N and C—H⋯O interactions that extend along the b axis.

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

C₂₃H₂₃N₅OS
M_r = 417.52
Triclinic, $[P \overline 1]$
a = 10.280 (3) Å
b = 12.413 (2) Å
c = 17.671 (4) Å
α = 74.290 (9)°
β = 87.96 (1)°
γ = 68.281 (7)°
V = 2011.3 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 153 K
0.40 × 0.40 × 0.23 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008 ) T_min = 0.929, T_max = 0.958
19475 measured reflections
9061 independent reflections
6741 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.115
S = 1.03
9061 reflections
551 parameters
H-atom parameters constrained
Δρ_max = 0.34 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—H0⋯N3′ⁱ	0.88	2.27	3.151 (2)	177
N5′—H0′⋯N3ⁱ	0.88	2.24	3.089 (2)	164
C22—H22B⋯O1ⁱⁱ	0.98	2.57	3.500 (2)	159
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+1, -z.

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/S1600536810053559/ng5080sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810053559/ng5080Isup2.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 benzene ring makes opposite angles with thiazole-pyrimidine ring. 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 2.48 (8)°. The aniline rings (C1/C2/C3/C4/C5/C6/N1) and (C14/C15/C16/C17/C18/C19/N5) make dihedral angles of 53.06 (8) Å and 19.21 (8) Å with the thiazole ring, respectively. In contrast, in the other independent molecule, the thiazole ring (S1'/C7'/N2'/C8'/C9') and the pyrimidine ring (C10'/C11'/C12'/N3'/C13'/N4') make a dihedral angle of 12.82 (8)°. The aniline rings (C1'/C2'/C3'/C4'/C5'/C6'/N1') and (C14'/C15'/C16'/C17'/C18'/C19'/N5') make dihedral angles of 51.09 (9) Å and 29.07 (9) Å with the thiazole ring, respectively. Moreover, there exist different bond lengths in the two independent molecules due to different intermolecular hydrogen bonding interactions (Table 1). The crystal structure is stabilized by intermolecular weak N—H···N and C—H···O interactions, which extending down b axis.

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-(methyl-p-tolyl-amino)-4-methyl-thiazol-5-yl]-propenone (1.575 g, 5 mmol) and NaOH (0.2 g, 5 mmol) in 2-methoxylethanol (35 ml) was treated with N-(3-Methoxy-phenyl)-guanidine carbonate (1.476 g, 6.5 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 THF affored the title compound as brown-yellow crystals, 0.97 g, m.p.453–456 K, yield 46.7%.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.): 8.27 (s, 1H, J = 4.8 Hz, py—H), 7.53 (s, 1H, Ar—H), 7.29–7.07 (m, 5H, Ar—H), 6.87 (d, 1H,J = 8.0 Hz, Ar—H), 6.83 (d, 1H, J = 5.2 Hz, py—H), 6.54 (d, 1H, J = 8.0 Hz, Ar—H), 3.64 (s, 3H, OCH₃), 3.54 (s, 3H, CH₃), 2.60 (s, 3H, CH₃), 2.41 (s, 3H, CH₃). EIMS m/z (%): 417 (M⁺,100), 402 (7), 311 (12), 105 (9), 91 (10), 73 (12), 57 (17).

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 b axis. Dashed lines denote intermolecular N—H···N and C—H···O hydrogen bonds.

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

Crystal data top

C₂₃H₂₃N₅OS	Z = 4
M_r = 417.52	F(000) = 880
Triclinic, P1	D_x = 1.379 Mg m⁻³
Hall symbol: -P 1	Melting point = 456–453 K
a = 10.280 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.413 (2) Å	Cell parameters from 5913 reflections
c = 17.671 (4) Å	θ = 3.0–27.5°
α = 74.290 (9)°	µ = 0.19 mm⁻¹
β = 87.96 (1)°	T = 153 K
γ = 68.281 (7)°	Block, yellow
V = 2011.3 (8) Å³	0.40 × 0.40 × 0.23 mm

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	9061 independent reflections
Radiation source: fine-focus sealed tube	6741 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
phi and ω scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008)	k = −16→12
T_min = 0.929, T_max = 0.958	l = −22→21
19475 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0641P)²] where P = (F_o² + 2F_c²)/3
9061 reflections	(Δ/σ)_max = 0.002
551 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₃H₂₃N₅OS	γ = 68.281 (7)°
M_r = 417.52	V = 2011.3 (8) Å³
Triclinic, P1	Z = 4
a = 10.280 (3) Å	Mo Kα radiation
b = 12.413 (2) Å	µ = 0.19 mm⁻¹
c = 17.671 (4) Å	T = 153 K
α = 74.290 (9)°	0.40 × 0.40 × 0.23 mm
β = 87.96 (1)°

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	9061 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008)	6741 reflections with I > 2σ(I)
T_min = 0.929, T_max = 0.958	R_int = 0.028
19475 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.03	Δρ_max = 0.34 e Å⁻³
9061 reflections	Δρ_min = −0.25 e Å⁻³
551 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	0.50315 (4)	0.38212 (4)	0.11927 (2)	0.02004 (11)
O1	0.31361 (12)	0.76460 (10)	0.16457 (7)	0.0297 (3)
N1	0.74892 (14)	0.22921 (12)	0.20606 (8)	0.0237 (3)
N2	0.66177 (14)	0.16781 (12)	0.11226 (8)	0.0215 (3)
N3	0.07766 (14)	0.54098 (12)	−0.08838 (8)	0.0226 (3)
N4	0.25101 (14)	0.50344 (11)	0.01314 (7)	0.0183 (3)
C1	0.61409 (18)	0.34713 (15)	0.29291 (9)	0.0233 (4)
H1	0.5369	0.3255	0.2855	0.028*
C2	0.60597 (19)	0.41897 (16)	0.34179 (10)	0.0287 (4)
H2	0.5222	0.4465	0.3674	0.034*
C3	0.7163 (2)	0.45221 (16)	0.35466 (10)	0.0301 (4)
C4	0.8380 (2)	0.40956 (16)	0.31677 (10)	0.0307 (4)
H4	0.9158	0.4298	0.3252	0.037*
C5	0.84791 (18)	0.33830 (16)	0.26710 (10)	0.0264 (4)
H5	0.9317	0.3108	0.2414	0.032*
C6	0.73559 (17)	0.30653 (14)	0.25448 (9)	0.0202 (3)
C7	0.64954 (17)	0.24899 (14)	0.14957 (9)	0.0204 (3)
C8	0.55242 (17)	0.20873 (14)	0.05698 (9)	0.0203 (3)
C9	0.45492 (16)	0.32321 (14)	0.05084 (9)	0.0186 (3)
C10	0.32638 (16)	0.39460 (14)	0.00112 (9)	0.0186 (3)
C11	0.27980 (18)	0.35759 (15)	−0.05700 (10)	0.0257 (4)
H11	0.3320	0.2823	−0.0668	0.031*
C12	0.15554 (18)	0.43451 (15)	−0.09934 (10)	0.0266 (4)
H12	0.1230	0.4102	−0.1391	0.032*
C13	0.13195 (16)	0.57067 (14)	−0.03208 (9)	0.0191 (3)
C14	0.06599 (17)	0.74316 (14)	0.02929 (9)	0.0202 (3)
C15	−0.05486 (18)	0.83747 (15)	0.03962 (10)	0.0272 (4)
H15	−0.1416	0.8547	0.0126	0.033*
C16	−0.04857 (19)	0.90526 (16)	0.08867 (10)	0.0316 (4)
H16	−0.1305	0.9703	0.0941	0.038*
C17	0.07593 (19)	0.87930 (15)	0.12995 (10)	0.0278 (4)
H17	0.0801	0.9256	0.1641	0.033*
C18	0.19478 (17)	0.78470 (14)	0.12089 (10)	0.0225 (4)
C19	0.19246 (17)	0.71745 (14)	0.07009 (9)	0.0213 (4)
H19	0.2757	0.6549	0.0632	0.026*
C20	0.7059 (3)	0.52907 (19)	0.40976 (12)	0.0483 (6)
H20A	0.7917	0.5462	0.4096	0.058*
H20B	0.6946	0.4857	0.4633	0.058*
H20C	0.6248	0.6051	0.3921	0.058*
C21	0.87705 (18)	0.12023 (16)	0.21626 (11)	0.0303 (4)
H21A	0.8514	0.0509	0.2184	0.036*
H21B	0.9303	0.1054	0.2654	0.036*
H21C	0.9348	0.1318	0.1717	0.036*
C22	0.55248 (19)	0.12289 (15)	0.01110 (10)	0.0276 (4)
H22A	0.6287	0.0447	0.0330	0.033*
H22B	0.5664	0.1557	−0.0442	0.033*
H22C	0.4624	0.1123	0.0147	0.033*
C23	0.42224 (18)	0.64788 (16)	0.17922 (11)	0.0312 (4)
H23A	0.3823	0.5860	0.1995	0.037*
H23B	0.4933	0.6396	0.2182	0.037*
H23C	0.4658	0.6378	0.1301	0.037*
S1'	0.62905 (4)	0.02186 (4)	0.35481 (2)	0.02269 (11)
O1'	0.32556 (14)	0.34116 (11)	0.45343 (7)	0.0364 (3)
N1'	0.86877 (15)	−0.12792 (13)	0.44911 (8)	0.0268 (3)
N2'	0.81090 (15)	−0.18076 (13)	0.34154 (9)	0.0273 (3)
N3'	0.21894 (15)	0.16941 (12)	0.14055 (8)	0.0236 (3)
N4'	0.39489 (14)	0.14313 (11)	0.23753 (8)	0.0188 (3)
C1'	0.80415 (18)	0.07463 (16)	0.46503 (10)	0.0269 (4)
H1'	0.8030	0.1065	0.4096	0.032*
C2'	0.7700 (2)	0.15134 (17)	0.51301 (11)	0.0312 (4)
H2'	0.7424	0.2357	0.4895	0.037*
C3'	0.7748 (2)	0.10854 (18)	0.59446 (11)	0.0336 (4)
C4'	0.8157 (2)	−0.01508 (18)	0.62604 (11)	0.0324 (4)
H4'	0.8218	−0.0473	0.6816	0.039*
C5'	0.84775 (19)	−0.09272 (17)	0.57929 (10)	0.0279 (4)
H5'	0.8753	−0.1770	0.6030	0.033*
C6'	0.84012 (17)	−0.04864 (16)	0.49739 (10)	0.0250 (4)
C7'	0.78435 (17)	−0.10428 (15)	0.38390 (10)	0.0237 (4)
C8'	0.70529 (18)	−0.14324 (15)	0.28392 (10)	0.0259 (4)
C9'	0.59585 (17)	−0.03712 (14)	0.28235 (9)	0.0212 (4)
C10'	0.46677 (17)	0.02952 (14)	0.23224 (9)	0.0204 (3)
C11'	0.41421 (19)	−0.01837 (16)	0.18333 (10)	0.0269 (4)
H11'	0.4618	−0.0989	0.1807	0.032*
C12'	0.29073 (19)	0.05571 (15)	0.13900 (10)	0.0270 (4)
H12'	0.2542	0.0242	0.1052	0.032*
C13'	0.27571 (17)	0.20653 (14)	0.19190 (9)	0.0195 (3)
C14'	0.20829 (16)	0.38181 (14)	0.24965 (9)	0.0194 (3)
C15'	0.13941 (18)	0.50655 (15)	0.22759 (10)	0.0260 (4)
H15'	0.0979	0.5474	0.1755	0.031*
C16'	0.1311 (2)	0.57126 (16)	0.28114 (12)	0.0328 (4)
H16'	0.0825	0.6563	0.2658	0.039*
C17'	0.1926 (2)	0.51390 (16)	0.35649 (11)	0.0327 (4)
H17'	0.1850	0.5586	0.3935	0.039*
C18'	0.26553 (18)	0.39037 (16)	0.37766 (10)	0.0251 (4)
C19'	0.27451 (17)	0.32300 (15)	0.32526 (9)	0.0210 (3)
H19'	0.3249	0.2382	0.3405	0.025*
C20'	0.7379 (3)	0.1922 (2)	0.64597 (13)	0.0567 (7)
H20D	0.6760	0.1704	0.6856	0.068*
H20E	0.6897	0.2754	0.6136	0.068*
H20F	0.8238	0.1856	0.6724	0.068*
C21'	0.96868 (19)	−0.25356 (16)	0.47869 (12)	0.0358 (5)
H21D	0.9171	−0.3061	0.5006	0.043*
H21E	1.0339	−0.2588	0.5199	0.043*
H21F	1.0214	−0.2794	0.4353	0.043*
C22'	0.7241 (2)	−0.22037 (18)	0.22881 (12)	0.0422 (5)
H22D	0.8231	−0.2735	0.2320	0.051*
H22E	0.6952	−0.1686	0.1747	0.051*
H22F	0.6664	−0.2693	0.2438	0.051*
C23'	0.4145 (2)	0.21765 (16)	0.47661 (10)	0.0311 (4)
H23D	0.3615	0.1684	0.4712	0.037*
H23E	0.4501	0.1951	0.5317	0.037*
H23F	0.4936	0.2039	0.4430	0.037*
N5	0.05080 (14)	0.68186 (12)	−0.02343 (8)	0.0225 (3)
H0	−0.0238	0.7215	−0.0569	0.036 (6)*
N5'	0.19792 (14)	0.32157 (12)	0.19486 (8)	0.0212 (3)
H0'	0.1314	0.3641	0.1567	0.029 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01671 (19)	0.0193 (2)	0.0227 (2)	−0.00196 (15)	−0.00337 (16)	−0.00978 (17)
O1	0.0243 (6)	0.0262 (7)	0.0397 (7)	−0.0040 (5)	−0.0083 (6)	−0.0170 (6)
N1	0.0176 (7)	0.0247 (8)	0.0249 (7)	0.0006 (6)	−0.0038 (6)	−0.0121 (6)
N2	0.0193 (7)	0.0222 (7)	0.0209 (7)	−0.0032 (5)	−0.0003 (6)	−0.0090 (6)
N3	0.0186 (7)	0.0256 (8)	0.0212 (7)	−0.0033 (6)	−0.0033 (6)	−0.0094 (6)
N4	0.0169 (6)	0.0182 (7)	0.0180 (7)	−0.0034 (5)	0.0000 (5)	−0.0067 (5)
C1	0.0204 (8)	0.0272 (9)	0.0201 (8)	−0.0070 (7)	−0.0018 (7)	−0.0053 (7)
C2	0.0279 (9)	0.0303 (10)	0.0222 (9)	−0.0042 (7)	0.0002 (7)	−0.0076 (8)
C3	0.0407 (11)	0.0258 (9)	0.0211 (9)	−0.0085 (8)	−0.0074 (8)	−0.0065 (7)
C4	0.0348 (10)	0.0340 (10)	0.0270 (9)	−0.0183 (8)	−0.0060 (8)	−0.0056 (8)
C5	0.0233 (9)	0.0352 (10)	0.0213 (9)	−0.0132 (7)	0.0009 (7)	−0.0059 (8)
C6	0.0199 (8)	0.0206 (8)	0.0163 (8)	−0.0041 (6)	−0.0031 (6)	−0.0036 (7)
C7	0.0177 (8)	0.0201 (8)	0.0207 (8)	−0.0041 (6)	0.0008 (6)	−0.0052 (7)
C8	0.0205 (8)	0.0204 (8)	0.0196 (8)	−0.0053 (6)	0.0023 (6)	−0.0084 (7)
C9	0.0179 (8)	0.0200 (8)	0.0185 (8)	−0.0054 (6)	0.0003 (6)	−0.0084 (7)
C10	0.0165 (7)	0.0203 (8)	0.0186 (8)	−0.0055 (6)	0.0018 (6)	−0.0071 (7)
C11	0.0212 (8)	0.0255 (9)	0.0292 (9)	−0.0010 (7)	−0.0036 (7)	−0.0160 (8)
C12	0.0244 (9)	0.0309 (10)	0.0253 (9)	−0.0064 (7)	−0.0042 (7)	−0.0141 (8)
C13	0.0181 (8)	0.0217 (8)	0.0162 (8)	−0.0061 (6)	0.0017 (6)	−0.0054 (6)
C14	0.0224 (8)	0.0186 (8)	0.0178 (8)	−0.0044 (6)	−0.0012 (7)	−0.0064 (7)
C15	0.0222 (9)	0.0257 (9)	0.0271 (9)	0.0008 (7)	−0.0066 (7)	−0.0099 (8)
C16	0.0251 (9)	0.0278 (10)	0.0356 (10)	0.0027 (7)	−0.0046 (8)	−0.0160 (8)
C17	0.0290 (9)	0.0237 (9)	0.0311 (10)	−0.0038 (7)	−0.0019 (8)	−0.0162 (8)
C18	0.0218 (8)	0.0205 (8)	0.0252 (9)	−0.0073 (7)	−0.0023 (7)	−0.0064 (7)
C19	0.0190 (8)	0.0201 (8)	0.0233 (8)	−0.0041 (6)	0.0005 (7)	−0.0081 (7)
C20	0.0673 (16)	0.0416 (12)	0.0410 (12)	−0.0169 (11)	−0.0073 (11)	−0.0226 (10)
C21	0.0207 (9)	0.0302 (10)	0.0326 (10)	0.0022 (7)	−0.0060 (8)	−0.0126 (8)
C22	0.0285 (9)	0.0221 (9)	0.0294 (9)	−0.0019 (7)	−0.0033 (8)	−0.0130 (7)
C23	0.0217 (9)	0.0282 (10)	0.0412 (11)	−0.0024 (7)	−0.0087 (8)	−0.0139 (8)
S1'	0.0201 (2)	0.0222 (2)	0.0229 (2)	−0.00219 (16)	−0.00535 (17)	−0.00906 (17)
O1'	0.0433 (8)	0.0365 (8)	0.0248 (7)	−0.0039 (6)	−0.0043 (6)	−0.0159 (6)
N1'	0.0207 (7)	0.0268 (8)	0.0279 (8)	−0.0031 (6)	−0.0071 (6)	−0.0064 (6)
N2'	0.0223 (7)	0.0244 (8)	0.0308 (8)	−0.0016 (6)	−0.0017 (6)	−0.0104 (7)
N3'	0.0215 (7)	0.0252 (8)	0.0238 (7)	−0.0068 (6)	−0.0044 (6)	−0.0081 (6)
N4'	0.0176 (7)	0.0187 (7)	0.0187 (7)	−0.0053 (5)	−0.0003 (5)	−0.0049 (5)
C1'	0.0254 (9)	0.0333 (10)	0.0225 (9)	−0.0136 (7)	−0.0051 (7)	−0.0040 (8)
C2'	0.0342 (10)	0.0330 (10)	0.0298 (10)	−0.0180 (8)	−0.0047 (8)	−0.0057 (8)
C3'	0.0375 (11)	0.0421 (12)	0.0317 (10)	−0.0235 (9)	0.0017 (8)	−0.0145 (9)
C4'	0.0332 (10)	0.0455 (12)	0.0233 (9)	−0.0225 (9)	−0.0010 (8)	−0.0057 (8)
C5'	0.0252 (9)	0.0315 (10)	0.0254 (9)	−0.0137 (7)	−0.0068 (7)	−0.0001 (8)
C6'	0.0160 (8)	0.0310 (10)	0.0280 (9)	−0.0091 (7)	−0.0041 (7)	−0.0071 (8)
C7'	0.0194 (8)	0.0235 (9)	0.0250 (9)	−0.0052 (7)	−0.0009 (7)	−0.0052 (7)
C8'	0.0240 (9)	0.0236 (9)	0.0286 (9)	−0.0041 (7)	0.0000 (7)	−0.0112 (7)
C9'	0.0229 (8)	0.0195 (8)	0.0200 (8)	−0.0057 (7)	−0.0022 (7)	−0.0062 (7)
C10'	0.0221 (8)	0.0208 (8)	0.0175 (8)	−0.0072 (6)	0.0006 (7)	−0.0050 (7)
C11'	0.0287 (9)	0.0236 (9)	0.0281 (9)	−0.0069 (7)	−0.0039 (8)	−0.0101 (7)
C12'	0.0310 (10)	0.0288 (10)	0.0245 (9)	−0.0114 (8)	−0.0038 (8)	−0.0114 (8)
C13'	0.0190 (8)	0.0224 (8)	0.0165 (8)	−0.0081 (6)	0.0017 (6)	−0.0043 (7)
C14'	0.0133 (7)	0.0231 (8)	0.0230 (8)	−0.0077 (6)	0.0025 (6)	−0.0070 (7)
C15'	0.0223 (9)	0.0244 (9)	0.0295 (9)	−0.0076 (7)	−0.0030 (7)	−0.0057 (7)
C16'	0.0289 (10)	0.0208 (9)	0.0463 (12)	−0.0051 (7)	−0.0039 (9)	−0.0105 (8)
C17'	0.0318 (10)	0.0302 (10)	0.0396 (11)	−0.0071 (8)	0.0013 (9)	−0.0213 (9)
C18'	0.0223 (8)	0.0304 (9)	0.0239 (9)	−0.0086 (7)	0.0015 (7)	−0.0114 (7)
C19'	0.0178 (8)	0.0220 (8)	0.0233 (8)	−0.0063 (6)	0.0033 (7)	−0.0082 (7)
C20'	0.091 (2)	0.0563 (15)	0.0408 (13)	−0.0408 (14)	0.0134 (13)	−0.0252 (11)
C21'	0.0256 (10)	0.0303 (10)	0.0405 (11)	0.0005 (8)	−0.0110 (9)	−0.0064 (9)
C22'	0.0319 (11)	0.0401 (12)	0.0520 (13)	0.0012 (9)	−0.0059 (10)	−0.0285 (10)
C23'	0.0325 (10)	0.0335 (10)	0.0235 (9)	−0.0081 (8)	−0.0051 (8)	−0.0073 (8)
N5	0.0193 (7)	0.0212 (7)	0.0225 (7)	−0.0002 (6)	−0.0070 (6)	−0.0083 (6)
N5'	0.0179 (7)	0.0220 (7)	0.0209 (7)	−0.0035 (5)	−0.0043 (6)	−0.0064 (6)

Geometric parameters (Å, º) top

S1—C7	1.7377 (16)	S1'—C7'	1.7427 (17)
S1—C9	1.7414 (16)	O1'—C18'	1.372 (2)
O1—C18	1.3739 (19)	O1'—C23'	1.416 (2)
O1—C23	1.4259 (19)	N1'—C7'	1.366 (2)
N1—C7	1.362 (2)	N1'—C6'	1.416 (2)
N1—C6	1.418 (2)	N1'—C21'	1.474 (2)
N1—C21	1.4709 (19)	N2'—C7'	1.309 (2)
N2—C7	1.314 (2)	N2'—C8'	1.371 (2)
N2—C8	1.365 (2)	N3'—C12'	1.336 (2)
N3—C12	1.330 (2)	N3'—C13'	1.356 (2)
N3—C13	1.352 (2)	N4'—C13'	1.336 (2)
N4—C13	1.3362 (19)	N4'—C10'	1.356 (2)
N4—C10	1.3563 (19)	C1'—C2'	1.385 (2)
C1—C2	1.380 (2)	C1'—C6'	1.388 (2)
C1—C6	1.391 (2)	C1'—H1'	0.9500
C1—H1	0.9500	C2'—C3'	1.389 (3)
C2—C3	1.387 (3)	C2'—H2'	0.9500
C2—H2	0.9500	C3'—C4'	1.385 (3)
C3—C4	1.391 (3)	C3'—C20'	1.499 (3)
C3—C20	1.513 (2)	C4'—C5'	1.377 (3)
C4—C5	1.382 (2)	C4'—H4'	0.9500
C4—H4	0.9500	C5'—C6'	1.395 (2)
C5—C6	1.393 (2)	C5'—H5'	0.9500
C5—H5	0.9500	C8'—C9'	1.374 (2)
C8—C9	1.381 (2)	C8'—C22'	1.502 (2)
C8—C22	1.503 (2)	C9'—C10'	1.450 (2)
C9—C10	1.448 (2)	C10'—C11'	1.393 (2)
C10—C11	1.396 (2)	C11'—C12'	1.374 (2)
C11—C12	1.372 (2)	C11'—H11'	0.9500
C11—H11	0.9500	C12'—H12'	0.9500
C12—H12	0.9500	C13'—N5'	1.369 (2)
C13—N5	1.370 (2)	C14'—C15'	1.390 (2)
C14—C19	1.395 (2)	C14'—C19'	1.396 (2)
C14—N5	1.398 (2)	C14'—N5'	1.402 (2)
C14—C15	1.404 (2)	C15'—C16'	1.380 (2)
C15—C16	1.379 (2)	C15'—H15'	0.9500
C15—H15	0.9500	C16'—C17'	1.376 (3)
C16—C17	1.381 (2)	C16'—H16'	0.9500
C16—H16	0.9500	C17'—C18'	1.383 (2)
C17—C18	1.387 (2)	C17'—H17'	0.9500
C17—H17	0.9500	C18'—C19'	1.386 (2)
C18—C19	1.388 (2)	C19'—H19'	0.9500
C19—H19	0.9500	C20'—H20D	0.9800
C20—H20A	0.9800	C20'—H20E	0.9800
C20—H20B	0.9800	C20'—H20F	0.9800
C20—H20C	0.9800	C21'—H21D	0.9800
C21—H21A	0.9800	C21'—H21E	0.9800
C21—H21B	0.9800	C21'—H21F	0.9800
C21—H21C	0.9800	C22'—H22D	0.9800
C22—H22A	0.9800	C22'—H22E	0.9800
C22—H22B	0.9800	C22'—H22F	0.9800
C22—H22C	0.9800	C23'—H23D	0.9800
C23—H23A	0.9800	C23'—H23E	0.9800
C23—H23B	0.9800	C23'—H23F	0.9800
C23—H23C	0.9800	N5—H0	0.8800
S1'—C9'	1.7367 (16)	N5'—H0'	0.8800

C7—S1—C9	88.64 (8)	C7'—N1'—C21'	115.57 (15)
C18—O1—C23	116.99 (13)	C6'—N1'—C21'	119.97 (14)
C7—N1—C6	124.09 (13)	C7'—N2'—C8'	110.83 (14)
C7—N1—C21	116.77 (14)	C12'—N3'—C13'	114.45 (14)
C6—N1—C21	119.14 (13)	C13'—N4'—C10'	116.72 (14)
C7—N2—C8	110.62 (13)	C2'—C1'—C6'	120.40 (16)
C12—N3—C13	114.57 (13)	C2'—C1'—H1'	119.8
C13—N4—C10	117.02 (14)	C6'—C1'—H1'	119.8
C2—C1—C6	119.79 (17)	C1'—C2'—C3'	121.91 (18)
C2—C1—H1	120.1	C1'—C2'—H2'	119.0
C6—C1—H1	120.1	C3'—C2'—H2'	119.0
C1—C2—C3	122.08 (17)	C4'—C3'—C2'	116.98 (18)
C1—C2—H2	119.0	C4'—C3'—C20'	121.47 (18)
C3—C2—H2	119.0	C2'—C3'—C20'	121.55 (18)
C2—C3—C4	117.55 (17)	C5'—C4'—C3'	122.02 (17)
C2—C3—C20	121.09 (19)	C5'—C4'—H4'	119.0
C4—C3—C20	121.34 (19)	C3'—C4'—H4'	119.0
C5—C4—C3	121.29 (17)	C4'—C5'—C6'	120.58 (17)
C5—C4—H4	119.4	C4'—C5'—H5'	119.7
C3—C4—H4	119.4	C6'—C5'—H5'	119.7
C4—C5—C6	120.32 (17)	C1'—C6'—C5'	118.04 (16)
C4—C5—H5	119.8	C1'—C6'—N1'	121.29 (15)
C6—C5—H5	119.8	C5'—C6'—N1'	120.66 (16)
C1—C6—C5	118.96 (16)	N2'—C7'—N1'	121.33 (15)
C1—C6—N1	121.09 (15)	N2'—C7'—S1'	115.06 (12)
C5—C6—N1	119.88 (15)	N1'—C7'—S1'	123.46 (13)
N2—C7—N1	121.04 (14)	N2'—C8'—C9'	115.64 (15)
N2—C7—S1	115.41 (12)	N2'—C8'—C22'	116.69 (15)
N1—C7—S1	123.51 (13)	C9'—C8'—C22'	127.65 (16)
N2—C8—C9	115.91 (14)	C8'—C9'—C10'	131.90 (15)
N2—C8—C22	115.90 (14)	C8'—C9'—S1'	109.75 (12)
C9—C8—C22	128.19 (15)	C10'—C9'—S1'	118.34 (12)
C8—C9—C10	131.61 (15)	N4'—C10'—C11'	120.66 (14)
C8—C9—S1	109.42 (12)	N4'—C10'—C9'	115.53 (14)
C10—C9—S1	118.95 (12)	C11'—C10'—C9'	123.78 (15)
N4—C10—C11	120.22 (14)	C12'—C11'—C10'	117.26 (16)
N4—C10—C9	116.07 (14)	C12'—C11'—H11'	121.4
C11—C10—C9	123.70 (14)	C10'—C11'—H11'	121.4
C12—C11—C10	117.24 (15)	N3'—C12'—C11'	123.97 (16)
C12—C11—H11	121.4	N3'—C12'—H12'	118.0
C10—C11—H11	121.4	C11'—C12'—H12'	118.0
N3—C12—C11	124.25 (15)	N4'—C13'—N3'	126.86 (15)
N3—C12—H12	117.9	N4'—C13'—N5'	119.53 (14)
C11—C12—H12	117.9	N3'—C13'—N5'	113.61 (14)
N4—C13—N3	126.68 (14)	C15'—C14'—C19'	119.57 (15)
N4—C13—N5	120.21 (14)	C15'—C14'—N5'	116.54 (14)
N3—C13—N5	113.11 (13)	C19'—C14'—N5'	123.74 (14)
C19—C14—N5	124.14 (14)	C16'—C15'—C14'	120.21 (16)
C19—C14—C15	119.27 (15)	C16'—C15'—H15'	119.9
N5—C14—C15	116.57 (14)	C14'—C15'—H15'	119.9
C16—C15—C14	120.50 (16)	C17'—C16'—C15'	120.70 (17)
C16—C15—H15	119.7	C17'—C16'—H16'	119.6
C14—C15—H15	119.7	C15'—C16'—H16'	119.6
C15—C16—C17	120.48 (16)	C16'—C17'—C18'	119.15 (17)
C15—C16—H16	119.8	C16'—C17'—H17'	120.4
C17—C16—H16	119.8	C18'—C17'—H17'	120.4
C16—C17—C18	119.04 (16)	O1'—C18'—C17'	115.16 (15)
C16—C17—H17	120.5	O1'—C18'—C19'	123.49 (15)
C18—C17—H17	120.5	C17'—C18'—C19'	121.34 (16)
O1—C18—C17	115.16 (15)	C18'—C19'—C14'	118.95 (15)
O1—C18—C19	123.15 (14)	C18'—C19'—H19'	120.5
C17—C18—C19	121.68 (15)	C14'—C19'—H19'	120.5
C18—C19—C14	118.98 (15)	C3'—C20'—H20D	109.5
C18—C19—H19	120.5	C3'—C20'—H20E	109.5
C14—C19—H19	120.5	H20D—C20'—H20E	109.5
C3—C20—H20A	109.5	C3'—C20'—H20F	109.5
C3—C20—H20B	109.5	H20D—C20'—H20F	109.5
H20A—C20—H20B	109.5	H20E—C20'—H20F	109.5
C3—C20—H20C	109.5	N1'—C21'—H21D	109.5
H20A—C20—H20C	109.5	N1'—C21'—H21E	109.5
H20B—C20—H20C	109.5	H21D—C21'—H21E	109.5
N1—C21—H21A	109.5	N1'—C21'—H21F	109.5
N1—C21—H21B	109.5	H21D—C21'—H21F	109.5
H21A—C21—H21B	109.5	H21E—C21'—H21F	109.5
N1—C21—H21C	109.5	C8'—C22'—H22D	109.5
H21A—C21—H21C	109.5	C8'—C22'—H22E	109.5
H21B—C21—H21C	109.5	H22D—C22'—H22E	109.5
C8—C22—H22A	109.5	C8'—C22'—H22F	109.5
C8—C22—H22B	109.5	H22D—C22'—H22F	109.5
H22A—C22—H22B	109.5	H22E—C22'—H22F	109.5
C8—C22—H22C	109.5	O1'—C23'—H23D	109.5
H22A—C22—H22C	109.5	O1'—C23'—H23E	109.5
H22B—C22—H22C	109.5	H23D—C23'—H23E	109.5
O1—C23—H23A	109.5	O1'—C23'—H23F	109.5
O1—C23—H23B	109.5	H23D—C23'—H23F	109.5
H23A—C23—H23B	109.5	H23E—C23'—H23F	109.5
O1—C23—H23C	109.5	C13—N5—C14	131.15 (13)
H23A—C23—H23C	109.5	C13—N5—H0	114.4
H23B—C23—H23C	109.5	C14—N5—H0	114.4
C9'—S1'—C7'	88.66 (8)	C13'—N5'—C14'	129.69 (13)
C18'—O1'—C23'	118.32 (13)	C13'—N5'—H0'	115.2
C7'—N1'—C6'	122.53 (14)	C14'—N5'—H0'	115.2

C6—C1—C2—C3	−0.4 (3)	C20'—C3'—C4'—C5'	178.9 (2)
C1—C2—C3—C4	−0.5 (3)	C3'—C4'—C5'—C6'	0.1 (3)
C1—C2—C3—C20	−178.81 (17)	C2'—C1'—C6'—C5'	−3.3 (3)
C2—C3—C4—C5	1.0 (3)	C2'—C1'—C6'—N1'	176.88 (16)
C20—C3—C4—C5	179.31 (17)	C4'—C5'—C6'—C1'	2.2 (3)
C3—C4—C5—C6	−0.6 (3)	C4'—C5'—C6'—N1'	−178.01 (16)
C2—C1—C6—C5	0.8 (2)	C7'—N1'—C6'—C1'	−46.7 (3)
C2—C1—C6—N1	177.79 (14)	C21'—N1'—C6'—C1'	149.80 (17)
C4—C5—C6—C1	−0.3 (2)	C7'—N1'—C6'—C5'	133.47 (18)
C4—C5—C6—N1	−177.33 (15)	C21'—N1'—C6'—C5'	−30.0 (2)
C7—N1—C6—C1	48.2 (2)	C8'—N2'—C7'—N1'	174.26 (16)
C21—N1—C6—C1	−131.79 (17)	C8'—N2'—C7'—S1'	−1.4 (2)
C7—N1—C6—C5	−134.82 (18)	C6'—N1'—C7'—N2'	−177.96 (16)
C21—N1—C6—C5	45.2 (2)	C21'—N1'—C7'—N2'	−13.8 (3)
C8—N2—C7—N1	−178.21 (15)	C6'—N1'—C7'—S1'	−2.7 (3)
C8—N2—C7—S1	−0.28 (19)	C21'—N1'—C7'—S1'	161.47 (14)
C6—N1—C7—N2	−172.95 (15)	C9'—S1'—C7'—N2'	2.15 (15)
C21—N1—C7—N2	7.1 (2)	C9'—S1'—C7'—N1'	−173.40 (17)
C6—N1—C7—S1	9.3 (2)	C7'—N2'—C8'—C9'	−0.5 (2)
C21—N1—C7—S1	−170.69 (13)	C7'—N2'—C8'—C22'	177.95 (17)
C9—S1—C7—N2	0.00 (14)	N2'—C8'—C9'—C10'	−178.95 (18)
C9—S1—C7—N1	177.87 (16)	C22'—C8'—C9'—C10'	2.9 (3)
C7—N2—C8—C9	0.5 (2)	N2'—C8'—C9'—S1'	2.0 (2)
C7—N2—C8—C22	−178.81 (15)	C22'—C8'—C9'—S1'	−176.16 (17)
N2—C8—C9—C10	−178.73 (17)	C7'—S1'—C9'—C8'	−2.23 (14)
C22—C8—C9—C10	0.5 (3)	C7'—S1'—C9'—C10'	178.60 (15)
N2—C8—C9—S1	−0.52 (19)	C13'—N4'—C10'—C11'	−2.3 (2)
C22—C8—C9—S1	178.71 (15)	C13'—N4'—C10'—C9'	179.90 (15)
C7—S1—C9—C8	0.28 (13)	C8'—C9'—C10'—N4'	−167.75 (18)
C7—S1—C9—C10	178.75 (14)	S1'—C9'—C10'—N4'	11.2 (2)
C13—N4—C10—C11	0.7 (2)	C8'—C9'—C10'—C11'	14.5 (3)
C13—N4—C10—C9	−179.93 (15)	S1'—C9'—C10'—C11'	−166.56 (14)
C8—C9—C10—N4	177.00 (17)	N4'—C10'—C11'—C12'	2.5 (3)
S1—C9—C10—N4	−1.1 (2)	C9'—C10'—C11'—C12'	−179.83 (17)
C8—C9—C10—C11	−3.7 (3)	C13'—N3'—C12'—C11'	−1.8 (3)
S1—C9—C10—C11	178.22 (14)	C10'—C11'—C12'—N3'	−0.4 (3)
N4—C10—C11—C12	−1.0 (3)	C10'—N4'—C13'—N3'	−0.2 (3)
C9—C10—C11—C12	179.69 (17)	C10'—N4'—C13'—N5'	179.63 (15)
C13—N3—C12—C11	1.3 (3)	C12'—N3'—C13'—N4'	2.2 (3)
C10—C11—C12—N3	−0.1 (3)	C12'—N3'—C13'—N5'	−177.63 (15)
C10—N4—C13—N3	0.7 (3)	C19'—C14'—C15'—C16'	−2.9 (3)
C10—N4—C13—N5	−179.70 (15)	N5'—C14'—C15'—C16'	172.79 (16)
C12—N3—C13—N4	−1.7 (3)	C14'—C15'—C16'—C17'	1.1 (3)
C12—N3—C13—N5	178.67 (15)	C15'—C16'—C17'—C18'	1.3 (3)
C19—C14—C15—C16	0.9 (3)	C23'—O1'—C18'—C17'	−173.22 (17)
N5—C14—C15—C16	−178.00 (16)	C23'—O1'—C18'—C19'	7.4 (3)
C14—C15—C16—C17	−1.7 (3)	C16'—C17'—C18'—O1'	178.81 (18)
C15—C16—C17—C18	0.5 (3)	C16'—C17'—C18'—C19'	−1.8 (3)
C23—O1—C18—C17	158.88 (17)	O1'—C18'—C19'—C14'	179.33 (16)
C23—O1—C18—C19	−22.2 (2)	C17'—C18'—C19'—C14'	0.0 (3)
C16—C17—C18—O1	−179.50 (16)	C15'—C14'—C19'—C18'	2.3 (2)
C16—C17—C18—C19	1.5 (3)	N5'—C14'—C19'—C18'	−173.03 (15)
O1—C18—C19—C14	178.81 (15)	N4—C13—N5—C14	−2.6 (3)
C17—C18—C19—C14	−2.3 (3)	N3—C13—N5—C14	177.09 (16)
N5—C14—C19—C18	179.88 (15)	C19—C14—N5—C13	20.4 (3)
C15—C14—C19—C18	1.1 (3)	C15—C14—N5—C13	−160.71 (17)
C6'—C1'—C2'—C3'	2.3 (3)	N4'—C13'—N5'—C14'	−12.8 (3)
C1'—C2'—C3'—C4'	0.0 (3)	N3'—C13'—N5'—C14'	167.01 (16)
C1'—C2'—C3'—C20'	179.9 (2)	C15'—C14'—N5'—C13'	164.55 (17)
C2'—C3'—C4'—C5'	−1.2 (3)	C19'—C14'—N5'—C13'	−20.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H0···N3′ⁱ	0.88	2.27	3.151 (2)	177
N5′—H0′···N3ⁱ	0.88	2.24	3.089 (2)	164
C22—H22B···O1ⁱⁱ	0.98	2.57	3.500 (2)	159

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₃N₅OS
M_r	417.52
Crystal system, space group	Triclinic, P1
Temperature (K)	153
a, b, c (Å)	10.280 (3), 12.413 (2), 17.671 (4)
α, β, γ (°)	74.290 (9), 87.96 (1), 68.281 (7)
V (Å³)	2011.3 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.40 × 0.40 × 0.23

Data collection
Diffractometer	Rigaku AFC10/Saturn724+ diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2008)
T_min, T_max	0.929, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	19475, 9061, 6741
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.115, 1.03
No. of reflections	9061
No. of parameters	551
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −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—H0···N3'ⁱ	0.88	2.27	3.151 (2)	177
N5'—H0'···N3ⁱ	0.88	2.24	3.089 (2)	164
C22—H22B···O1ⁱⁱ	0.98	2.57	3.500 (2)	159

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z.

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 o261

doi:10.1107/S1600536810053559

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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