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

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ISSN: 2056-9890

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

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[Narayana, B., Raj, K. K. V., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2004). Eur. J. Med. Chem. 39, 867-872.]). For the synthesis of the title compound, see: Bredereck et al. (1964[Bredereck, H., Effenberger, F. & Botsch, H. (1964). Chem. Ber. 97, 3397-3406.]).

[Scheme 1]

Experimental

Crystal data
  • C23H23N5OS

  • Mr = 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[Rigaku/MSC (2008). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) Tmin = 0.929, Tmax = 0.958

  • 19475 measured reflections

  • 9061 independent reflections

  • 6741 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.115

  • S = 1.03

  • 9061 reflections

  • 551 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Rigaku/MSC (2008). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


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).

Refinement top

All H atoms were placed in calculated positions (C—H 0.95–0.98 Å, N—H 0.87–0.89 Å) and refined as riding with Uiso(H) = 1.2–1.22Ueq of the parent atom.

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
[Figure 1] Fig. 1. The structure of (I), shown with 30% probability displacement ellipsoids.
[Figure 2] 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
C23H23N5OSZ = 4
Mr = 417.52F(000) = 880
Triclinic, P1Dx = 1.379 Mg m3
Hall symbol: -P 1Melting point = 456–453 K
a = 10.280 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.413 (2) ÅCell parameters from 5913 reflections
c = 17.671 (4) Åθ = 3.0–27.5°
α = 74.290 (9)°µ = 0.19 mm1
β = 87.96 (1)°T = 153 K
γ = 68.281 (7)°Block, yellow
V = 2011.3 (8) Å30.40 × 0.40 × 0.23 mm
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
9061 independent reflections
Radiation source: fine-focus sealed tube6741 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 28.5714 pixels mm-1θmax = 27.5°, θmin = 3.1°
phi and ω scansh = 1313
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2008)
k = 1612
Tmin = 0.929, Tmax = 0.958l = 2221
19475 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0641P)2]
where P = (Fo2 + 2Fc2)/3
9061 reflections(Δ/σ)max = 0.002
551 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C23H23N5OSγ = 68.281 (7)°
Mr = 417.52V = 2011.3 (8) Å3
Triclinic, P1Z = 4
a = 10.280 (3) ÅMo Kα radiation
b = 12.413 (2) ŵ = 0.19 mm1
c = 17.671 (4) ÅT = 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)
Tmin = 0.929, Tmax = 0.958Rint = 0.028
19475 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 1.03Δρmax = 0.34 e Å3
9061 reflectionsΔρmin = 0.25 e Å3
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
xyzUiso*/Ueq
S10.50315 (4)0.38212 (4)0.11927 (2)0.02004 (11)
O10.31361 (12)0.76460 (10)0.16457 (7)0.0297 (3)
N10.74892 (14)0.22921 (12)0.20606 (8)0.0237 (3)
N20.66177 (14)0.16781 (12)0.11226 (8)0.0215 (3)
N30.07766 (14)0.54098 (12)0.08838 (8)0.0226 (3)
N40.25101 (14)0.50344 (11)0.01314 (7)0.0183 (3)
C10.61409 (18)0.34713 (15)0.29291 (9)0.0233 (4)
H10.53690.32550.28550.028*
C20.60597 (19)0.41897 (16)0.34179 (10)0.0287 (4)
H20.52220.44650.36740.034*
C30.7163 (2)0.45221 (16)0.35466 (10)0.0301 (4)
C40.8380 (2)0.40956 (16)0.31677 (10)0.0307 (4)
H40.91580.42980.32520.037*
C50.84791 (18)0.33830 (16)0.26710 (10)0.0264 (4)
H50.93170.31080.24140.032*
C60.73559 (17)0.30653 (14)0.25448 (9)0.0202 (3)
C70.64954 (17)0.24899 (14)0.14957 (9)0.0204 (3)
C80.55242 (17)0.20873 (14)0.05698 (9)0.0203 (3)
C90.45492 (16)0.32321 (14)0.05084 (9)0.0186 (3)
C100.32638 (16)0.39460 (14)0.00112 (9)0.0186 (3)
C110.27980 (18)0.35759 (15)0.05700 (10)0.0257 (4)
H110.33200.28230.06680.031*
C120.15554 (18)0.43451 (15)0.09934 (10)0.0266 (4)
H120.12300.41020.13910.032*
C130.13195 (16)0.57067 (14)0.03208 (9)0.0191 (3)
C140.06599 (17)0.74316 (14)0.02929 (9)0.0202 (3)
C150.05486 (18)0.83747 (15)0.03962 (10)0.0272 (4)
H150.14160.85470.01260.033*
C160.04857 (19)0.90526 (16)0.08867 (10)0.0316 (4)
H160.13050.97030.09410.038*
C170.07593 (19)0.87930 (15)0.12995 (10)0.0278 (4)
H170.08010.92560.16410.033*
C180.19478 (17)0.78470 (14)0.12089 (10)0.0225 (4)
C190.19246 (17)0.71745 (14)0.07009 (9)0.0213 (4)
H190.27570.65490.06320.026*
C200.7059 (3)0.52907 (19)0.40976 (12)0.0483 (6)
H20A0.79170.54620.40960.058*
H20B0.69460.48570.46330.058*
H20C0.62480.60510.39210.058*
C210.87705 (18)0.12023 (16)0.21626 (11)0.0303 (4)
H21A0.85140.05090.21840.036*
H21B0.93030.10540.26540.036*
H21C0.93480.13180.17170.036*
C220.55248 (19)0.12289 (15)0.01110 (10)0.0276 (4)
H22A0.62870.04470.03300.033*
H22B0.56640.15570.04420.033*
H22C0.46240.11230.01470.033*
C230.42224 (18)0.64788 (16)0.17922 (11)0.0312 (4)
H23A0.38230.58600.19950.037*
H23B0.49330.63960.21820.037*
H23C0.46580.63780.13010.037*
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)
H1'0.80300.10650.40960.032*
C2'0.7700 (2)0.15134 (17)0.51301 (11)0.0312 (4)
H2'0.74240.23570.48950.037*
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)
H4'0.82180.04730.68160.039*
C5'0.84775 (19)0.09272 (17)0.57929 (10)0.0279 (4)
H5'0.87530.17700.60300.033*
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)
H11'0.46180.09890.18070.032*
C12'0.29073 (19)0.05571 (15)0.13900 (10)0.0270 (4)
H12'0.25420.02420.10520.032*
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)
H15'0.09790.54740.17550.031*
C16'0.1311 (2)0.57126 (16)0.28114 (12)0.0328 (4)
H16'0.08250.65630.26580.039*
C17'0.1926 (2)0.51390 (16)0.35649 (11)0.0327 (4)
H17'0.18500.55860.39350.039*
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)
H19'0.32490.23820.34050.025*
C20'0.7379 (3)0.1922 (2)0.64597 (13)0.0567 (7)
H20D0.67600.17040.68560.068*
H20E0.68970.27540.61360.068*
H20F0.82380.18560.67240.068*
C21'0.96868 (19)0.25356 (16)0.47869 (12)0.0358 (5)
H21D0.91710.30610.50060.043*
H21E1.03390.25880.51990.043*
H21F1.02140.27940.43530.043*
C22'0.7241 (2)0.22037 (18)0.22881 (12)0.0422 (5)
H22D0.82310.27350.23200.051*
H22E0.69520.16860.17470.051*
H22F0.66640.26930.24380.051*
C23'0.4145 (2)0.21765 (16)0.47661 (10)0.0311 (4)
H23D0.36150.16840.47120.037*
H23E0.45010.19510.53170.037*
H23F0.49360.20390.44300.037*
N50.05080 (14)0.68186 (12)0.02343 (8)0.0225 (3)
H00.02380.72150.05690.036 (6)*
N5'0.19792 (14)0.32157 (12)0.19486 (8)0.0212 (3)
H0'0.13140.36410.15670.029 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01671 (19)0.0193 (2)0.0227 (2)0.00196 (15)0.00337 (16)0.00978 (17)
O10.0243 (6)0.0262 (7)0.0397 (7)0.0040 (5)0.0083 (6)0.0170 (6)
N10.0176 (7)0.0247 (8)0.0249 (7)0.0006 (6)0.0038 (6)0.0121 (6)
N20.0193 (7)0.0222 (7)0.0209 (7)0.0032 (5)0.0003 (6)0.0090 (6)
N30.0186 (7)0.0256 (8)0.0212 (7)0.0033 (6)0.0033 (6)0.0094 (6)
N40.0169 (6)0.0182 (7)0.0180 (7)0.0034 (5)0.0000 (5)0.0067 (5)
C10.0204 (8)0.0272 (9)0.0201 (8)0.0070 (7)0.0018 (7)0.0053 (7)
C20.0279 (9)0.0303 (10)0.0222 (9)0.0042 (7)0.0002 (7)0.0076 (8)
C30.0407 (11)0.0258 (9)0.0211 (9)0.0085 (8)0.0074 (8)0.0065 (7)
C40.0348 (10)0.0340 (10)0.0270 (9)0.0183 (8)0.0060 (8)0.0056 (8)
C50.0233 (9)0.0352 (10)0.0213 (9)0.0132 (7)0.0009 (7)0.0059 (8)
C60.0199 (8)0.0206 (8)0.0163 (8)0.0041 (6)0.0031 (6)0.0036 (7)
C70.0177 (8)0.0201 (8)0.0207 (8)0.0041 (6)0.0008 (6)0.0052 (7)
C80.0205 (8)0.0204 (8)0.0196 (8)0.0053 (6)0.0023 (6)0.0084 (7)
C90.0179 (8)0.0200 (8)0.0185 (8)0.0054 (6)0.0003 (6)0.0084 (7)
C100.0165 (7)0.0203 (8)0.0186 (8)0.0055 (6)0.0018 (6)0.0071 (7)
C110.0212 (8)0.0255 (9)0.0292 (9)0.0010 (7)0.0036 (7)0.0160 (8)
C120.0244 (9)0.0309 (10)0.0253 (9)0.0064 (7)0.0042 (7)0.0141 (8)
C130.0181 (8)0.0217 (8)0.0162 (8)0.0061 (6)0.0017 (6)0.0054 (6)
C140.0224 (8)0.0186 (8)0.0178 (8)0.0044 (6)0.0012 (7)0.0064 (7)
C150.0222 (9)0.0257 (9)0.0271 (9)0.0008 (7)0.0066 (7)0.0099 (8)
C160.0251 (9)0.0278 (10)0.0356 (10)0.0027 (7)0.0046 (8)0.0160 (8)
C170.0290 (9)0.0237 (9)0.0311 (10)0.0038 (7)0.0019 (8)0.0162 (8)
C180.0218 (8)0.0205 (8)0.0252 (9)0.0073 (7)0.0023 (7)0.0064 (7)
C190.0190 (8)0.0201 (8)0.0233 (8)0.0041 (6)0.0005 (7)0.0081 (7)
C200.0673 (16)0.0416 (12)0.0410 (12)0.0169 (11)0.0073 (11)0.0226 (10)
C210.0207 (9)0.0302 (10)0.0326 (10)0.0022 (7)0.0060 (8)0.0126 (8)
C220.0285 (9)0.0221 (9)0.0294 (9)0.0019 (7)0.0033 (8)0.0130 (7)
C230.0217 (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)
N50.0193 (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—C71.7377 (16)S1'—C7'1.7427 (17)
S1—C91.7414 (16)O1'—C18'1.372 (2)
O1—C181.3739 (19)O1'—C23'1.416 (2)
O1—C231.4259 (19)N1'—C7'1.366 (2)
N1—C71.362 (2)N1'—C6'1.416 (2)
N1—C61.418 (2)N1'—C21'1.474 (2)
N1—C211.4709 (19)N2'—C7'1.309 (2)
N2—C71.314 (2)N2'—C8'1.371 (2)
N2—C81.365 (2)N3'—C12'1.336 (2)
N3—C121.330 (2)N3'—C13'1.356 (2)
N3—C131.352 (2)N4'—C13'1.336 (2)
N4—C131.3362 (19)N4'—C10'1.356 (2)
N4—C101.3563 (19)C1'—C2'1.385 (2)
C1—C21.380 (2)C1'—C6'1.388 (2)
C1—C61.391 (2)C1'—H1'0.9500
C1—H10.9500C2'—C3'1.389 (3)
C2—C31.387 (3)C2'—H2'0.9500
C2—H20.9500C3'—C4'1.385 (3)
C3—C41.391 (3)C3'—C20'1.499 (3)
C3—C201.513 (2)C4'—C5'1.377 (3)
C4—C51.382 (2)C4'—H4'0.9500
C4—H40.9500C5'—C6'1.395 (2)
C5—C61.393 (2)C5'—H5'0.9500
C5—H50.9500C8'—C9'1.374 (2)
C8—C91.381 (2)C8'—C22'1.502 (2)
C8—C221.503 (2)C9'—C10'1.450 (2)
C9—C101.448 (2)C10'—C11'1.393 (2)
C10—C111.396 (2)C11'—C12'1.374 (2)
C11—C121.372 (2)C11'—H11'0.9500
C11—H110.9500C12'—H12'0.9500
C12—H120.9500C13'—N5'1.369 (2)
C13—N51.370 (2)C14'—C15'1.390 (2)
C14—C191.395 (2)C14'—C19'1.396 (2)
C14—N51.398 (2)C14'—N5'1.402 (2)
C14—C151.404 (2)C15'—C16'1.380 (2)
C15—C161.379 (2)C15'—H15'0.9500
C15—H150.9500C16'—C17'1.376 (3)
C16—C171.381 (2)C16'—H16'0.9500
C16—H160.9500C17'—C18'1.383 (2)
C17—C181.387 (2)C17'—H17'0.9500
C17—H170.9500C18'—C19'1.386 (2)
C18—C191.388 (2)C19'—H19'0.9500
C19—H190.9500C20'—H20D0.9800
C20—H20A0.9800C20'—H20E0.9800
C20—H20B0.9800C20'—H20F0.9800
C20—H20C0.9800C21'—H21D0.9800
C21—H21A0.9800C21'—H21E0.9800
C21—H21B0.9800C21'—H21F0.9800
C21—H21C0.9800C22'—H22D0.9800
C22—H22A0.9800C22'—H22E0.9800
C22—H22B0.9800C22'—H22F0.9800
C22—H22C0.9800C23'—H23D0.9800
C23—H23A0.9800C23'—H23E0.9800
C23—H23B0.9800C23'—H23F0.9800
C23—H23C0.9800N5—H00.8800
S1'—C9'1.7367 (16)N5'—H0'0.8800
C7—S1—C988.64 (8)C7'—N1'—C21'115.57 (15)
C18—O1—C23116.99 (13)C6'—N1'—C21'119.97 (14)
C7—N1—C6124.09 (13)C7'—N2'—C8'110.83 (14)
C7—N1—C21116.77 (14)C12'—N3'—C13'114.45 (14)
C6—N1—C21119.14 (13)C13'—N4'—C10'116.72 (14)
C7—N2—C8110.62 (13)C2'—C1'—C6'120.40 (16)
C12—N3—C13114.57 (13)C2'—C1'—H1'119.8
C13—N4—C10117.02 (14)C6'—C1'—H1'119.8
C2—C1—C6119.79 (17)C1'—C2'—C3'121.91 (18)
C2—C1—H1120.1C1'—C2'—H2'119.0
C6—C1—H1120.1C3'—C2'—H2'119.0
C1—C2—C3122.08 (17)C4'—C3'—C2'116.98 (18)
C1—C2—H2119.0C4'—C3'—C20'121.47 (18)
C3—C2—H2119.0C2'—C3'—C20'121.55 (18)
C2—C3—C4117.55 (17)C5'—C4'—C3'122.02 (17)
C2—C3—C20121.09 (19)C5'—C4'—H4'119.0
C4—C3—C20121.34 (19)C3'—C4'—H4'119.0
C5—C4—C3121.29 (17)C4'—C5'—C6'120.58 (17)
C5—C4—H4119.4C4'—C5'—H5'119.7
C3—C4—H4119.4C6'—C5'—H5'119.7
C4—C5—C6120.32 (17)C1'—C6'—C5'118.04 (16)
C4—C5—H5119.8C1'—C6'—N1'121.29 (15)
C6—C5—H5119.8C5'—C6'—N1'120.66 (16)
C1—C6—C5118.96 (16)N2'—C7'—N1'121.33 (15)
C1—C6—N1121.09 (15)N2'—C7'—S1'115.06 (12)
C5—C6—N1119.88 (15)N1'—C7'—S1'123.46 (13)
N2—C7—N1121.04 (14)N2'—C8'—C9'115.64 (15)
N2—C7—S1115.41 (12)N2'—C8'—C22'116.69 (15)
N1—C7—S1123.51 (13)C9'—C8'—C22'127.65 (16)
N2—C8—C9115.91 (14)C8'—C9'—C10'131.90 (15)
N2—C8—C22115.90 (14)C8'—C9'—S1'109.75 (12)
C9—C8—C22128.19 (15)C10'—C9'—S1'118.34 (12)
C8—C9—C10131.61 (15)N4'—C10'—C11'120.66 (14)
C8—C9—S1109.42 (12)N4'—C10'—C9'115.53 (14)
C10—C9—S1118.95 (12)C11'—C10'—C9'123.78 (15)
N4—C10—C11120.22 (14)C12'—C11'—C10'117.26 (16)
N4—C10—C9116.07 (14)C12'—C11'—H11'121.4
C11—C10—C9123.70 (14)C10'—C11'—H11'121.4
C12—C11—C10117.24 (15)N3'—C12'—C11'123.97 (16)
C12—C11—H11121.4N3'—C12'—H12'118.0
C10—C11—H11121.4C11'—C12'—H12'118.0
N3—C12—C11124.25 (15)N4'—C13'—N3'126.86 (15)
N3—C12—H12117.9N4'—C13'—N5'119.53 (14)
C11—C12—H12117.9N3'—C13'—N5'113.61 (14)
N4—C13—N3126.68 (14)C15'—C14'—C19'119.57 (15)
N4—C13—N5120.21 (14)C15'—C14'—N5'116.54 (14)
N3—C13—N5113.11 (13)C19'—C14'—N5'123.74 (14)
C19—C14—N5124.14 (14)C16'—C15'—C14'120.21 (16)
C19—C14—C15119.27 (15)C16'—C15'—H15'119.9
N5—C14—C15116.57 (14)C14'—C15'—H15'119.9
C16—C15—C14120.50 (16)C17'—C16'—C15'120.70 (17)
C16—C15—H15119.7C17'—C16'—H16'119.6
C14—C15—H15119.7C15'—C16'—H16'119.6
C15—C16—C17120.48 (16)C16'—C17'—C18'119.15 (17)
C15—C16—H16119.8C16'—C17'—H17'120.4
C17—C16—H16119.8C18'—C17'—H17'120.4
C16—C17—C18119.04 (16)O1'—C18'—C17'115.16 (15)
C16—C17—H17120.5O1'—C18'—C19'123.49 (15)
C18—C17—H17120.5C17'—C18'—C19'121.34 (16)
O1—C18—C17115.16 (15)C18'—C19'—C14'118.95 (15)
O1—C18—C19123.15 (14)C18'—C19'—H19'120.5
C17—C18—C19121.68 (15)C14'—C19'—H19'120.5
C18—C19—C14118.98 (15)C3'—C20'—H20D109.5
C18—C19—H19120.5C3'—C20'—H20E109.5
C14—C19—H19120.5H20D—C20'—H20E109.5
C3—C20—H20A109.5C3'—C20'—H20F109.5
C3—C20—H20B109.5H20D—C20'—H20F109.5
H20A—C20—H20B109.5H20E—C20'—H20F109.5
C3—C20—H20C109.5N1'—C21'—H21D109.5
H20A—C20—H20C109.5N1'—C21'—H21E109.5
H20B—C20—H20C109.5H21D—C21'—H21E109.5
N1—C21—H21A109.5N1'—C21'—H21F109.5
N1—C21—H21B109.5H21D—C21'—H21F109.5
H21A—C21—H21B109.5H21E—C21'—H21F109.5
N1—C21—H21C109.5C8'—C22'—H22D109.5
H21A—C21—H21C109.5C8'—C22'—H22E109.5
H21B—C21—H21C109.5H22D—C22'—H22E109.5
C8—C22—H22A109.5C8'—C22'—H22F109.5
C8—C22—H22B109.5H22D—C22'—H22F109.5
H22A—C22—H22B109.5H22E—C22'—H22F109.5
C8—C22—H22C109.5O1'—C23'—H23D109.5
H22A—C22—H22C109.5O1'—C23'—H23E109.5
H22B—C22—H22C109.5H23D—C23'—H23E109.5
O1—C23—H23A109.5O1'—C23'—H23F109.5
O1—C23—H23B109.5H23D—C23'—H23F109.5
H23A—C23—H23B109.5H23E—C23'—H23F109.5
O1—C23—H23C109.5C13—N5—C14131.15 (13)
H23A—C23—H23C109.5C13—N5—H0114.4
H23B—C23—H23C109.5C14—N5—H0114.4
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—C30.4 (3)C20'—C3'—C4'—C5'178.9 (2)
C1—C2—C3—C40.5 (3)C3'—C4'—C5'—C6'0.1 (3)
C1—C2—C3—C20178.81 (17)C2'—C1'—C6'—C5'3.3 (3)
C2—C3—C4—C51.0 (3)C2'—C1'—C6'—N1'176.88 (16)
C20—C3—C4—C5179.31 (17)C4'—C5'—C6'—C1'2.2 (3)
C3—C4—C5—C60.6 (3)C4'—C5'—C6'—N1'178.01 (16)
C2—C1—C6—C50.8 (2)C7'—N1'—C6'—C1'46.7 (3)
C2—C1—C6—N1177.79 (14)C21'—N1'—C6'—C1'149.80 (17)
C4—C5—C6—C10.3 (2)C7'—N1'—C6'—C5'133.47 (18)
C4—C5—C6—N1177.33 (15)C21'—N1'—C6'—C5'30.0 (2)
C7—N1—C6—C148.2 (2)C8'—N2'—C7'—N1'174.26 (16)
C21—N1—C6—C1131.79 (17)C8'—N2'—C7'—S1'1.4 (2)
C7—N1—C6—C5134.82 (18)C6'—N1'—C7'—N2'177.96 (16)
C21—N1—C6—C545.2 (2)C21'—N1'—C7'—N2'13.8 (3)
C8—N2—C7—N1178.21 (15)C6'—N1'—C7'—S1'2.7 (3)
C8—N2—C7—S10.28 (19)C21'—N1'—C7'—S1'161.47 (14)
C6—N1—C7—N2172.95 (15)C9'—S1'—C7'—N2'2.15 (15)
C21—N1—C7—N27.1 (2)C9'—S1'—C7'—N1'173.40 (17)
C6—N1—C7—S19.3 (2)C7'—N2'—C8'—C9'0.5 (2)
C21—N1—C7—S1170.69 (13)C7'—N2'—C8'—C22'177.95 (17)
C9—S1—C7—N20.00 (14)N2'—C8'—C9'—C10'178.95 (18)
C9—S1—C7—N1177.87 (16)C22'—C8'—C9'—C10'2.9 (3)
C7—N2—C8—C90.5 (2)N2'—C8'—C9'—S1'2.0 (2)
C7—N2—C8—C22178.81 (15)C22'—C8'—C9'—S1'176.16 (17)
N2—C8—C9—C10178.73 (17)C7'—S1'—C9'—C8'2.23 (14)
C22—C8—C9—C100.5 (3)C7'—S1'—C9'—C10'178.60 (15)
N2—C8—C9—S10.52 (19)C13'—N4'—C10'—C11'2.3 (2)
C22—C8—C9—S1178.71 (15)C13'—N4'—C10'—C9'179.90 (15)
C7—S1—C9—C80.28 (13)C8'—C9'—C10'—N4'167.75 (18)
C7—S1—C9—C10178.75 (14)S1'—C9'—C10'—N4'11.2 (2)
C13—N4—C10—C110.7 (2)C8'—C9'—C10'—C11'14.5 (3)
C13—N4—C10—C9179.93 (15)S1'—C9'—C10'—C11'166.56 (14)
C8—C9—C10—N4177.00 (17)N4'—C10'—C11'—C12'2.5 (3)
S1—C9—C10—N41.1 (2)C9'—C10'—C11'—C12'179.83 (17)
C8—C9—C10—C113.7 (3)C13'—N3'—C12'—C11'1.8 (3)
S1—C9—C10—C11178.22 (14)C10'—C11'—C12'—N3'0.4 (3)
N4—C10—C11—C121.0 (3)C10'—N4'—C13'—N3'0.2 (3)
C9—C10—C11—C12179.69 (17)C10'—N4'—C13'—N5'179.63 (15)
C13—N3—C12—C111.3 (3)C12'—N3'—C13'—N4'2.2 (3)
C10—C11—C12—N30.1 (3)C12'—N3'—C13'—N5'177.63 (15)
C10—N4—C13—N30.7 (3)C19'—C14'—C15'—C16'2.9 (3)
C10—N4—C13—N5179.70 (15)N5'—C14'—C15'—C16'172.79 (16)
C12—N3—C13—N41.7 (3)C14'—C15'—C16'—C17'1.1 (3)
C12—N3—C13—N5178.67 (15)C15'—C16'—C17'—C18'1.3 (3)
C19—C14—C15—C160.9 (3)C23'—O1'—C18'—C17'173.22 (17)
N5—C14—C15—C16178.00 (16)C23'—O1'—C18'—C19'7.4 (3)
C14—C15—C16—C171.7 (3)C16'—C17'—C18'—O1'178.81 (18)
C15—C16—C17—C180.5 (3)C16'—C17'—C18'—C19'1.8 (3)
C23—O1—C18—C17158.88 (17)O1'—C18'—C19'—C14'179.33 (16)
C23—O1—C18—C1922.2 (2)C17'—C18'—C19'—C14'0.0 (3)
C16—C17—C18—O1179.50 (16)C15'—C14'—C19'—C18'2.3 (2)
C16—C17—C18—C191.5 (3)N5'—C14'—C19'—C18'173.03 (15)
O1—C18—C19—C14178.81 (15)N4—C13—N5—C142.6 (3)
C17—C18—C19—C142.3 (3)N3—C13—N5—C14177.09 (16)
N5—C14—C19—C18179.88 (15)C19—C14—N5—C1320.4 (3)
C15—C14—C19—C181.1 (3)C15—C14—N5—C13160.71 (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···AD—HH···AD···AD—H···A
N5—H0···N3i0.882.273.151 (2)177
N5—H0···N3i0.882.243.089 (2)164
C22—H22B···O1ii0.982.573.500 (2)159
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC23H23N5OS
Mr417.52
Crystal system, space groupTriclinic, 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)
V3)2011.3 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.40 × 0.40 × 0.23
Data collection
DiffractometerRigaku AFC10/Saturn724+
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2008)
Tmin, Tmax0.929, 0.958
No. of measured, independent and
observed [I > 2σ(I)] reflections
19475, 9061, 6741
Rint0.028
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.115, 1.03
No. of reflections9061
No. of parameters551
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N5—H0···N3'i0.882.273.151 (2)177
N5'—H0'···N3i0.882.243.089 (2)164
C22—H22B···O1ii0.982.573.500 (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

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