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

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ISSN: 2056-9890

5-Anilino-3-benzyl­sulfanyl-6-(3-chloro­anilino)-1-phenyl-1H-pyrazolo­[3,4-d]pyrimidin-4(5H)-one

aSchool of Chemistry and Chemical Engneering, University of South China, Hengyang 421001, People's Republic of China, bCollege of Mathematics and Physical, University of South China, Hunan 421001, People's Republic of China, and cInstitute of Organic Synthesis, Central China Normal University, Wuhan 430079, People's Republic of China
*Correspondence e-mail: hqwang2009cn@yahoo.com.cn

(Received 5 May 2012; accepted 1 September 2012; online 8 September 2012)

In the title compound, C30H23ClN6OS, the benzyl, the 3-chloro­anilino, the phenyl and the anilino groups form dihedral angles of 85.95 (6), 29.63 (7), 28.55 (1) and 87.48 (6)°, respectively, with the pyrazolo­[3,4-d]pyrimidine unit [maximum deviation = 0.052 (2) Å]. An intra­molecular N—H⋯N hydrogen bond occurs. The crystal structure features N—H⋯O hydrogen bonds.

Related literature

For similar compounds, see: Wang et al. (2004[Wang, H. Q., Liu, Z. J. & Ding, M. W. (2004). Chin. J. Struct. Chem. 23, 1133-1137.], 2008[Wang, H. Q., Zhou, W. P., Wang, Y. Y. & Lin, C. R. (2008). J. Agric. Food Chem. 56, 7321-7325.]). For their applications, see: Bendich et al. (1954[Bendich, A., Russell, P. J. & Fox, J. J. (1954). J. Am. Chem. Soc. 76, 6073-6077.]); Ballell et al. (2007[Ballell, L., Field, R. A., Chung, G. A. C. & Young, R. J. (2007). Bioorg. Med. Chem. Lett. 17, 1736-1740.]); Holla et al. (2006[Holla, B. S., Mahalinga, M., Karthikeyan, M. S., Akberali, P. M. & Shetty, N. S. (2006). Bioorg. Med. Chem. 14, 2040-2047.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C30H23ClN6OS

  • Mr = 551.05

  • Triclinic, [P \overline 1]

  • a = 10.881 (5) Å

  • b = 10.948 (4) Å

  • c = 12.496 (5) Å

  • α = 103.824 (7)°

  • β = 109.725 (7)°

  • γ = 93.377 (7)°

  • V = 1344.7 (9) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.26 mm−1

  • T = 293 K

  • 0.42 × 0.40 × 0.36 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.771, Tmax = 1.000

  • 7799 measured reflections

  • 5440 independent reflections

  • 3418 reflections with I > 2σ(I)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.114

  • S = 1.01

  • 5440 reflections

  • 360 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N5—H5⋯N6 0.79 (2) 2.19 (2) 2.605 (3) 114 (2)
N6—H6⋯O1i 0.81 (2) 2.12 (2) 2.904 (3) 162 (2)
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

Supporting information


Comment top

Pyrazolo[3,4-d]pyrimidine derivatives are important heterocycles as purine analogs(Bendich et al.,1954). They are usually used due to their potency as antagonists, antifungal agents (Ballell et al., 2007; Holla et al., 2006) and agrochemicals (Wang et al., 2008). We have reported the synthesis and structure of pyrazolo[3,4-d]pyrimidin-4(5H)-one derivatives (Wang et al., 2004).

The molecule and packing diagrams of the title compound were shown in Figure 1 and 2, respectively. As shown in Fig.1, the N1=C1 and N3=C4 bonds are 1.318 (3) and 1.304 (3) Å, respectively, slightly shorter than the normal C=N bond (1.329 and 1.336 Å; Allen et al., 1987) but close to 1.314 (3) and 1.302 (3) Å in our previous report (Wang et al., 2004), and the C2=C3 distance is 1.388 (3) Å, longer than the typical C=C(1.384 Å; Allen et al., 1987). In the molecule, the N–C bonds are remarkably shorter than the normal N–C single bond(1.469 Å) and longer than the C=N double bond. The packing was stabilized by the intermolecular N–H···O hydrogen bond.

Related literature top

For similar compounds, see: Wang et al. (2004, 2008). For their applications, see: Bendich et al. (1954); Ballell et al. (2007); Holla et al. (2006). For standard bond lengths, see: Allen et al. (1987).

Experimental top

To a solution of iminophosphorane (2 mmol) in dry dichloromethane (20 ml) aryl isocyanate(2 mmol) was added under nitrogen atmosphere at room temperature. After the reaction mixture was stirred for 1.5 h, 0.231 g (2.0 mmol) m-chlorophenyl isocyanate was added, and the resulting mixture was stirred for an additional 30 min. Then the solvent was removed under reduced pressure, and 25 ml anhydrous ethanol and 1.5 ml of sodium ethoxide (3 mol/L) in ethanol were added to the mixture. After 3 h of stirring at room temperature, the solution was concentrated under reduced pressure and successively cooled. The crude product was collected by filtration. After recrystallization from DMF/petroleum ether or column chromatography on silica gel, white crystals were obtained.

Refinement top

H atoms were included in their idealized positions, with C—H = 0.96 Å, and refined using a riding model with Uiso(H) = 1.2 Ueq(C) for other H atoms.

Structure description top

Pyrazolo[3,4-d]pyrimidine derivatives are important heterocycles as purine analogs(Bendich et al.,1954). They are usually used due to their potency as antagonists, antifungal agents (Ballell et al., 2007; Holla et al., 2006) and agrochemicals (Wang et al., 2008). We have reported the synthesis and structure of pyrazolo[3,4-d]pyrimidin-4(5H)-one derivatives (Wang et al., 2004).

The molecule and packing diagrams of the title compound were shown in Figure 1 and 2, respectively. As shown in Fig.1, the N1=C1 and N3=C4 bonds are 1.318 (3) and 1.304 (3) Å, respectively, slightly shorter than the normal C=N bond (1.329 and 1.336 Å; Allen et al., 1987) but close to 1.314 (3) and 1.302 (3) Å in our previous report (Wang et al., 2004), and the C2=C3 distance is 1.388 (3) Å, longer than the typical C=C(1.384 Å; Allen et al., 1987). In the molecule, the N–C bonds are remarkably shorter than the normal N–C single bond(1.469 Å) and longer than the C=N double bond. The packing was stabilized by the intermolecular N–H···O hydrogen bond.

For similar compounds, see: Wang et al. (2004, 2008). For their applications, see: Bendich et al. (1954); Ballell et al. (2007); Holla et al. (2006). For standard bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008).

Figures top
[Figure 1] Fig. 1. View of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Hydrogen bonding pattern found in the title compound
5-Anilino-3-benzylsulfanyl-6-(3-chloroanilino)-1-phenyl-1H- pyrazolo[3,4-d]pyrimidin-4(5H)-one top
Crystal data top
C30H23ClN6OSZ = 2
Mr = 551.05F(000) = 572
Triclinic, P1Dx = 1.361 Mg m3
a = 10.881 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.948 (4) ÅCell parameters from 809 reflections
c = 12.496 (5) Åθ = 2.6–25.6°
α = 103.824 (7)°µ = 0.26 mm1
β = 109.725 (7)°T = 293 K
γ = 93.377 (7)°Block, white
V = 1344.7 (9) Å30.42 × 0.40 × 0.36 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
5440 independent reflections
Radiation source: fine-focus sealed tube3418 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
phi and ω scansθmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker 2000)
h = 139
Tmin = 0.771, Tmax = 1.000k = 1313
7799 measured reflectionsl = 915
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0437P)2 + 0.3561P]
where P = (Fo2 + 2Fc2)/3
5440 reflections(Δ/σ)max = 0.001
360 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
C30H23ClN6OSγ = 93.377 (7)°
Mr = 551.05V = 1344.7 (9) Å3
Triclinic, P1Z = 2
a = 10.881 (5) ÅMo Kα radiation
b = 10.948 (4) ŵ = 0.26 mm1
c = 12.496 (5) ÅT = 293 K
α = 103.824 (7)°0.42 × 0.40 × 0.36 mm
β = 109.725 (7)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
5440 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker 2000)
3418 reflections with I > 2σ(I)
Tmin = 0.771, Tmax = 1.000Rint = 0.022
7799 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.40 e Å3
5440 reflectionsΔρmin = 0.40 e Å3
360 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
Cl10.58922 (10)0.29645 (7)0.00499 (9)0.0950 (3)
S10.84719 (7)0.64314 (5)0.33369 (6)0.0557 (2)
N10.7368 (2)0.41189 (16)0.32750 (16)0.0462 (5)
N20.71298 (19)0.28629 (16)0.25760 (16)0.0422 (5)
N30.75420 (19)0.16942 (15)0.08617 (15)0.0395 (4)
N40.84282 (18)0.30693 (15)0.00045 (15)0.0359 (4)
N50.8107 (2)0.08909 (17)0.07736 (18)0.0448 (5)
H50.844 (2)0.108 (2)0.119 (2)0.045 (7)*
N60.8716 (2)0.31275 (17)0.10020 (17)0.0382 (5)
H60.944 (2)0.354 (2)0.0795 (18)0.034 (6)*
O10.89538 (16)0.52346 (13)0.07639 (13)0.0454 (4)
C10.7947 (2)0.47893 (19)0.27824 (19)0.0417 (5)
C20.8102 (2)0.40058 (18)0.17656 (18)0.0374 (5)
C30.7579 (2)0.27820 (19)0.16756 (18)0.0371 (5)
C40.8006 (2)0.18745 (18)0.00674 (18)0.0359 (5)
C50.8535 (2)0.42237 (19)0.08658 (18)0.0360 (5)
C60.8389 (3)0.6721 (2)0.4802 (2)0.0571 (7)
H6A0.75100.64030.47440.068*
H6B0.90180.62850.52720.068*
C70.8708 (2)0.8136 (2)0.5377 (2)0.0438 (6)
C80.7750 (3)0.8901 (2)0.5120 (2)0.0568 (7)
H80.69060.85370.45840.068*
C90.8016 (3)1.0192 (3)0.5641 (3)0.0661 (8)
H90.73531.06910.54620.079*
C100.9247 (3)1.0737 (3)0.6416 (3)0.0691 (8)
H100.94231.16080.67790.083*
C111.0216 (3)1.0016 (3)0.6661 (3)0.0770 (9)
H111.10631.03950.71810.092*
C120.9953 (3)0.8704 (3)0.6138 (2)0.0655 (8)
H121.06260.82140.63070.079*
C130.6338 (2)0.1923 (2)0.27856 (19)0.0421 (5)
C140.5503 (3)0.2301 (2)0.3367 (2)0.0567 (7)
H140.54540.31600.36240.068*
C150.4731 (3)0.1394 (3)0.3569 (2)0.0700 (8)
H150.41680.16500.39690.084*
C160.4787 (3)0.0121 (3)0.3187 (2)0.0657 (8)
H160.42750.04820.33350.079*
C170.5606 (3)0.0250 (2)0.2585 (2)0.0613 (7)
H170.56320.11120.23060.074*
C180.6397 (3)0.0644 (2)0.2385 (2)0.0537 (6)
H180.69620.03860.19860.064*
C190.7924 (2)0.04243 (19)0.08586 (19)0.0414 (5)
C200.7077 (3)0.0968 (2)0.0437 (2)0.0488 (6)
H200.65890.04760.00690.059*
C210.6971 (3)0.2271 (2)0.0578 (2)0.0554 (7)
C220.7651 (3)0.3030 (2)0.1140 (2)0.0629 (8)
H220.75670.39000.12190.075*
C230.8462 (3)0.2473 (2)0.1585 (2)0.0628 (7)
H230.89120.29780.19890.075*
C240.8620 (3)0.1173 (2)0.1443 (2)0.0532 (6)
H240.91850.08040.17340.064*
C250.7690 (2)0.34949 (17)0.18724 (18)0.0367 (5)
C260.7993 (3)0.3826 (2)0.2774 (2)0.0466 (6)
H260.88470.38400.27770.056*
C270.7010 (3)0.4132 (2)0.3663 (2)0.0621 (8)
H270.72060.43450.42710.075*
C280.5748 (3)0.4127 (3)0.3663 (2)0.0661 (8)
H280.50970.43400.42640.079*
C290.5450 (3)0.3804 (2)0.2768 (2)0.0599 (7)
H290.45970.38040.27630.072*
C300.6417 (2)0.3480 (2)0.1879 (2)0.0454 (6)
H300.62100.32500.12830.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1326 (8)0.0500 (4)0.1256 (7)0.0044 (4)0.0769 (6)0.0270 (5)
S10.0814 (5)0.0344 (3)0.0551 (4)0.0089 (3)0.0419 (4)0.0015 (3)
N10.0592 (13)0.0348 (10)0.0453 (11)0.0037 (9)0.0270 (10)0.0030 (9)
N20.0562 (13)0.0326 (10)0.0416 (11)0.0012 (9)0.0257 (10)0.0072 (8)
N30.0549 (12)0.0273 (9)0.0405 (10)0.0031 (8)0.0231 (9)0.0092 (8)
N40.0485 (12)0.0268 (9)0.0376 (10)0.0031 (8)0.0220 (9)0.0095 (8)
N50.0684 (15)0.0268 (9)0.0482 (12)0.0058 (9)0.0333 (11)0.0095 (9)
N60.0462 (13)0.0320 (10)0.0425 (11)0.0015 (9)0.0247 (10)0.0097 (8)
O10.0586 (11)0.0292 (8)0.0553 (10)0.0024 (7)0.0322 (8)0.0093 (7)
C10.0506 (15)0.0322 (11)0.0431 (13)0.0009 (10)0.0233 (11)0.0042 (10)
C20.0441 (14)0.0295 (11)0.0390 (12)0.0009 (9)0.0190 (10)0.0060 (9)
C30.0446 (14)0.0326 (11)0.0362 (12)0.0020 (10)0.0175 (10)0.0099 (9)
C40.0435 (14)0.0272 (10)0.0385 (12)0.0043 (9)0.0163 (10)0.0100 (9)
C50.0364 (13)0.0297 (11)0.0419 (12)0.0019 (9)0.0160 (10)0.0078 (9)
C60.081 (2)0.0429 (14)0.0478 (15)0.0009 (13)0.0318 (14)0.0046 (11)
C70.0543 (16)0.0395 (12)0.0403 (13)0.0015 (11)0.0266 (12)0.0035 (10)
C80.0528 (17)0.0561 (16)0.0603 (16)0.0026 (13)0.0232 (13)0.0114 (13)
C90.074 (2)0.0498 (16)0.085 (2)0.0168 (15)0.0418 (18)0.0178 (15)
C100.087 (2)0.0399 (14)0.087 (2)0.0006 (16)0.0523 (19)0.0005 (14)
C110.061 (2)0.0630 (19)0.083 (2)0.0084 (16)0.0222 (17)0.0132 (16)
C120.0561 (18)0.0586 (17)0.0715 (19)0.0141 (14)0.0196 (15)0.0030 (14)
C130.0484 (15)0.0421 (12)0.0358 (12)0.0045 (11)0.0161 (11)0.0122 (10)
C140.0707 (19)0.0505 (15)0.0511 (15)0.0058 (13)0.0332 (14)0.0051 (12)
C150.076 (2)0.077 (2)0.0628 (18)0.0123 (16)0.0422 (16)0.0110 (15)
C160.074 (2)0.0634 (18)0.0602 (17)0.0176 (15)0.0256 (15)0.0226 (14)
C170.077 (2)0.0452 (14)0.0671 (18)0.0042 (14)0.0309 (16)0.0218 (13)
C180.0669 (18)0.0450 (14)0.0590 (16)0.0046 (12)0.0314 (14)0.0204 (12)
C190.0525 (15)0.0284 (11)0.0404 (13)0.0054 (10)0.0145 (11)0.0079 (10)
C200.0653 (17)0.0320 (12)0.0514 (14)0.0056 (11)0.0260 (13)0.0089 (11)
C210.0706 (19)0.0365 (13)0.0586 (16)0.0001 (12)0.0230 (14)0.0150 (12)
C220.086 (2)0.0288 (12)0.0727 (19)0.0135 (13)0.0263 (17)0.0151 (13)
C230.075 (2)0.0366 (13)0.0789 (19)0.0184 (13)0.0331 (16)0.0098 (13)
C240.0639 (18)0.0365 (13)0.0624 (16)0.0082 (12)0.0292 (14)0.0103 (12)
C250.0520 (15)0.0214 (10)0.0363 (12)0.0018 (9)0.0186 (11)0.0046 (9)
C260.0625 (17)0.0385 (12)0.0442 (14)0.0022 (11)0.0292 (13)0.0083 (11)
C270.088 (2)0.0571 (16)0.0436 (15)0.0016 (15)0.0250 (15)0.0192 (13)
C280.075 (2)0.0660 (18)0.0525 (17)0.0097 (16)0.0115 (15)0.0254 (14)
C290.0521 (17)0.0617 (17)0.0612 (17)0.0069 (13)0.0148 (14)0.0173 (14)
C300.0495 (16)0.0426 (13)0.0473 (14)0.0013 (11)0.0214 (12)0.0140 (11)
Geometric parameters (Å, º) top
Cl1—C211.746 (3)C12—H120.9300
S1—C11.748 (2)C13—C141.367 (3)
S1—C61.816 (2)C13—C181.383 (3)
N1—C11.318 (3)C14—C151.386 (3)
N1—N21.397 (2)C14—H140.9300
N2—C31.357 (3)C15—C161.373 (4)
N2—C131.430 (3)C15—H150.9300
N3—C41.304 (3)C16—C171.369 (4)
N3—C31.357 (3)C16—H160.9300
N4—C41.389 (2)C17—C181.387 (3)
N4—N61.409 (2)C17—H170.9300
N4—C51.420 (3)C18—H180.9300
N5—C41.351 (3)C19—C201.376 (3)
N5—C191.415 (3)C19—C241.392 (3)
N5—H50.79 (2)C20—C211.388 (3)
N6—C251.426 (3)C20—H200.9300
N6—H60.81 (2)C21—C221.369 (4)
O1—C51.223 (2)C22—C231.375 (4)
C1—C21.421 (3)C22—H220.9300
C2—C31.388 (3)C23—C241.384 (3)
C2—C51.420 (3)C23—H230.9300
C6—C71.508 (3)C24—H240.9300
C6—H6A0.9700C25—C301.381 (3)
C6—H6B0.9700C25—C261.393 (3)
C7—C121.369 (4)C26—C271.382 (4)
C7—C81.377 (3)C26—H260.9300
C8—C91.375 (4)C27—C281.372 (4)
C8—H80.9300C27—H270.9300
C9—C101.357 (4)C28—C291.379 (4)
C9—H90.9300C28—H280.9300
C10—C111.351 (4)C29—C301.382 (3)
C10—H100.9300C29—H290.9300
C11—C121.396 (4)C30—H300.9300
C11—H110.9300
C1—S1—C6101.17 (11)C14—C13—C18120.3 (2)
C1—N1—N2105.43 (17)C14—C13—N2119.3 (2)
C3—N2—N1110.80 (16)C18—C13—N2120.4 (2)
C3—N2—C13129.75 (18)C13—C14—C15119.5 (2)
N1—N2—C13118.85 (17)C13—C14—H14120.2
C4—N3—C3113.84 (17)C15—C14—H14120.2
C4—N4—N6117.28 (16)C16—C15—C14120.9 (3)
C4—N4—C5123.97 (17)C16—C15—H15119.6
N6—N4—C5118.71 (15)C14—C15—H15119.6
C4—N5—C19128.2 (2)C17—C16—C15119.1 (2)
C4—N5—H5115.2 (17)C17—C16—H16120.4
C19—N5—H5115.4 (17)C15—C16—H16120.4
N4—N6—C25114.04 (18)C16—C17—C18120.8 (3)
N4—N6—H6109.4 (15)C16—C17—H17119.6
C25—N6—H6114.9 (15)C18—C17—H17119.6
N1—C1—C2111.45 (18)C13—C18—C17119.3 (2)
N1—C1—S1123.62 (16)C13—C18—H18120.4
C2—C1—S1124.93 (16)C17—C18—H18120.4
C3—C2—C5119.40 (19)C20—C19—C24120.6 (2)
C3—C2—C1105.10 (18)C20—C19—N5123.2 (2)
C5—C2—C1135.25 (19)C24—C19—N5116.2 (2)
N3—C3—N2125.70 (18)C19—C20—C21118.1 (2)
N3—C3—C2127.08 (19)C19—C20—H20120.9
N2—C3—C2107.21 (18)C21—C20—H20120.9
N3—C4—N5121.72 (19)C22—C21—C20122.6 (2)
N3—C4—N4123.69 (19)C22—C21—Cl1119.16 (19)
N5—C4—N4114.59 (19)C20—C21—Cl1118.2 (2)
O1—C5—C2128.6 (2)C21—C22—C23118.3 (2)
O1—C5—N4119.93 (19)C21—C22—H22120.9
C2—C5—N4111.51 (17)C23—C22—H22120.9
C7—C6—S1108.09 (16)C22—C23—C24121.1 (2)
C7—C6—H6A110.1C22—C23—H23119.4
S1—C6—H6A110.1C24—C23—H23119.4
C7—C6—H6B110.1C23—C24—C19119.2 (2)
S1—C6—H6B110.1C23—C24—H24120.4
H6A—C6—H6B108.4C19—C24—H24120.4
C12—C7—C8118.1 (2)C30—C25—C26119.7 (2)
C12—C7—C6121.6 (2)C30—C25—N6122.8 (2)
C8—C7—C6120.3 (2)C26—C25—N6117.5 (2)
C9—C8—C7121.3 (3)C27—C26—C25119.2 (2)
C9—C8—H8119.3C27—C26—H26120.4
C7—C8—H8119.3C25—C26—H26120.4
C10—C9—C8119.9 (3)C28—C27—C26121.0 (2)
C10—C9—H9120.1C28—C27—H27119.5
C8—C9—H9120.1C26—C27—H27119.5
C11—C10—C9120.1 (3)C27—C28—C29119.8 (3)
C11—C10—H10120.0C27—C28—H28120.1
C9—C10—H10120.0C29—C28—H28120.1
C10—C11—C12120.3 (3)C28—C29—C30120.0 (3)
C10—C11—H11119.9C28—C29—H29120.0
C12—C11—H11119.9C30—C29—H29120.0
C7—C12—C11120.3 (3)C25—C30—C29120.3 (2)
C7—C12—H12119.9C25—C30—H30119.8
C11—C12—H12119.9C29—C30—H30119.8
C1—N1—N2—C30.7 (3)C6—C7—C8—C9179.4 (2)
C1—N1—N2—C13171.3 (2)C7—C8—C9—C100.7 (4)
C4—N4—N6—C25100.4 (2)C8—C9—C10—C111.1 (4)
C5—N4—N6—C2577.3 (2)C9—C10—C11—C121.3 (5)
N2—N1—C1—C20.0 (3)C8—C7—C12—C112.0 (4)
N2—N1—C1—S1179.17 (17)C6—C7—C12—C11179.6 (2)
C6—S1—C1—N113.9 (2)C10—C11—C12—C70.3 (5)
C6—S1—C1—C2165.1 (2)C3—N2—C13—C14149.5 (2)
N1—C1—C2—C30.6 (3)N1—N2—C13—C1420.7 (3)
S1—C1—C2—C3178.52 (17)C3—N2—C13—C1829.3 (4)
N1—C1—C2—C5173.3 (2)N1—N2—C13—C18160.5 (2)
S1—C1—C2—C57.5 (4)C18—C13—C14—C151.0 (4)
C4—N3—C3—N2178.3 (2)N2—C13—C14—C15179.8 (2)
C4—N3—C3—C23.2 (3)C13—C14—C15—C160.4 (4)
N1—N2—C3—N3177.6 (2)C14—C15—C16—C170.9 (4)
C13—N2—C3—N311.5 (4)C15—C16—C17—C181.6 (4)
N1—N2—C3—C21.1 (3)C14—C13—C18—C170.3 (4)
C13—N2—C3—C2169.7 (2)N2—C13—C18—C17179.1 (2)
C5—C2—C3—N37.2 (4)C16—C17—C18—C131.0 (4)
C1—C2—C3—N3177.7 (2)C4—N5—C19—C2030.2 (4)
C5—C2—C3—N2174.1 (2)C4—N5—C19—C24152.2 (2)
C1—C2—C3—N21.0 (3)C24—C19—C20—C212.0 (4)
C3—N3—C4—N5176.6 (2)N5—C19—C20—C21179.5 (2)
C3—N3—C4—N43.8 (3)C19—C20—C21—C221.5 (4)
C19—N5—C4—N39.2 (4)C19—C20—C21—Cl1179.75 (19)
C19—N5—C4—N4171.1 (2)C20—C21—C22—C230.4 (4)
N6—N4—C4—N3170.6 (2)Cl1—C21—C22—C23177.8 (2)
C5—N4—C4—N36.9 (3)C21—C22—C23—C241.8 (4)
N6—N4—C4—N59.1 (3)C22—C23—C24—C191.3 (4)
C5—N4—C4—N5173.4 (2)C20—C19—C24—C230.7 (4)
C3—C2—C5—O1175.9 (2)N5—C19—C24—C23178.3 (2)
C1—C2—C5—O12.6 (5)N4—N6—C25—C3015.6 (3)
C3—C2—C5—N43.7 (3)N4—N6—C25—C26167.26 (17)
C1—C2—C5—N4177.0 (2)C30—C25—C26—C270.1 (3)
C4—N4—C5—O1177.8 (2)N6—C25—C26—C27177.1 (2)
N6—N4—C5—O14.7 (3)C25—C26—C27—C280.6 (4)
C4—N4—C5—C22.6 (3)C26—C27—C28—C290.4 (4)
N6—N4—C5—C2174.89 (19)C27—C28—C29—C300.4 (4)
C1—S1—C6—C7175.34 (19)C26—C25—C30—C290.7 (3)
S1—C6—C7—C1296.8 (3)N6—C25—C30—C29177.8 (2)
S1—C6—C7—C881.5 (3)C28—C29—C30—C250.9 (4)
C12—C7—C8—C92.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···N60.79 (2)2.19 (2)2.605 (3)114 (2)
N6—H6···O1i0.81 (2)2.12 (2)2.904 (3)162 (2)
Symmetry code: (i) x+2, y+1, z.

Experimental details

Crystal data
Chemical formulaC30H23ClN6OS
Mr551.05
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)10.881 (5), 10.948 (4), 12.496 (5)
α, β, γ (°)103.824 (7), 109.725 (7), 93.377 (7)
V3)1344.7 (9)
Z2
Radiation typeMo Kα
µ (mm1)0.26
Crystal size (mm)0.42 × 0.40 × 0.36
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker 2000)
Tmin, Tmax0.771, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
7799, 5440, 3418
Rint0.022
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.114, 1.01
No. of reflections5440
No. of parameters360
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.40, 0.40

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···N60.79 (2)2.19 (2)2.605 (3)114 (2)
N6—H6···O1i0.81 (2)2.12 (2)2.904 (3)162 (2)
Symmetry code: (i) x+2, y+1, z.
 

Acknowledgements

We gratefully acknowledge the service provided by the X-ray facility at the Department of Chemistry and Chemical Engineering, Hengyang Normal University. Financial support of this work by the National Science Foundation (No. 11175080) and by the Natural Science Fund of Hunan Province (No. 10 J J6025) is gratefully acknowledged.

References

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