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

Wang, H.-Q.; He, F.-F.; Wang, X.-F.; Zhou, W.-P.; Liu, Z.-J.

doi:10.1107/S1600536812037683

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2895

https://doi.org/10.1107/S1600536812037683

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

Hong-Qing Wang,^a ^* Fang-Fang He,^a Xiao-Feng Wang,^a Wei-Ping Zhou ^b and Zhao-Jie Liu ^c

^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 , 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

Crystal data

C₃₀H₂₃ClN₆OS
M_r = 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 ) T_min = 0.771, T_max = 1.000
7799 measured reflections
5440 independent reflections
3418 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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 and Mercury (Macrae et al., 2008 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812037683/rn2104sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S1600536812037683/rn2104Isup2.mol

Supporting information file. DOI: https://doi.org/10.1107/S1600536812037683/rn2104Isup3.mol

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812037683/rn2104Isup4.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812037683/rn2104Isup5.cml

checkCIF report

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.

Structure description 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).

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

	Fig. 1. View of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	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

C₃₀H₂₃ClN₆OS	Z = 2
M_r = 551.05	F(000) = 572
Triclinic, P1	D_x = 1.361 Mg m⁻³
a = 10.881 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.948 (4) Å	Cell parameters from 809 reflections
c = 12.496 (5) Å	θ = 2.6–25.6°
α = 103.824 (7)°	µ = 0.26 mm⁻¹
β = 109.725 (7)°	T = 293 K
γ = 93.377 (7)°	Block, white
V = 1344.7 (9) Å³	0.42 × 0.40 × 0.36 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	5440 independent reflections
Radiation source: fine-focus sealed tube	3418 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
phi and ω scans	θ_max = 26.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker 2000)	h = −13→9
T_min = 0.771, T_max = 1.000	k = −13→13
7799 measured reflections	l = −9→15

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0437P)² + 0.3561P] where P = (F_o² + 2F_c²)/3
5440 reflections	(Δ/σ)_max = 0.001
360 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₃₀H₂₃ClN₆OS	γ = 93.377 (7)°
M_r = 551.05	V = 1344.7 (9) Å³
Triclinic, P1	Z = 2
a = 10.881 (5) Å	Mo Kα radiation
b = 10.948 (4) Å	µ = 0.26 mm⁻¹
c = 12.496 (5) Å	T = 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)
T_min = 0.771, T_max = 1.000	R_int = 0.022
7799 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.40 e Å⁻³
5440 reflections	Δρ_min = −0.40 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Cl1	0.58922 (10)	−0.29645 (7)	−0.00499 (9)	0.0950 (3)
S1	0.84719 (7)	0.64314 (5)	0.33369 (6)	0.0557 (2)
N1	0.7368 (2)	0.41189 (16)	0.32750 (16)	0.0462 (5)
N2	0.71298 (19)	0.28629 (16)	0.25760 (16)	0.0422 (5)
N3	0.75420 (19)	0.16942 (15)	0.08617 (15)	0.0395 (4)
N4	0.84282 (18)	0.30693 (15)	0.00045 (15)	0.0359 (4)
N5	0.8107 (2)	0.08909 (17)	−0.07736 (18)	0.0448 (5)
H5	0.844 (2)	0.108 (2)	−0.119 (2)	0.045 (7)*
N6	0.8716 (2)	0.31275 (17)	−0.10020 (17)	0.0382 (5)
H6	0.944 (2)	0.354 (2)	−0.0795 (18)	0.034 (6)*
O1	0.89538 (16)	0.52346 (13)	0.07639 (13)	0.0454 (4)
C1	0.7947 (2)	0.47893 (19)	0.27824 (19)	0.0417 (5)
C2	0.8102 (2)	0.40058 (18)	0.17656 (18)	0.0374 (5)
C3	0.7579 (2)	0.27820 (19)	0.16756 (18)	0.0371 (5)
C4	0.8006 (2)	0.18745 (18)	0.00674 (18)	0.0359 (5)
C5	0.8535 (2)	0.42237 (19)	0.08658 (18)	0.0360 (5)
C6	0.8389 (3)	0.6721 (2)	0.4802 (2)	0.0571 (7)
H6A	0.7510	0.6403	0.4744	0.068*
H6B	0.9018	0.6285	0.5272	0.068*
C7	0.8708 (2)	0.8136 (2)	0.5377 (2)	0.0438 (6)
C8	0.7750 (3)	0.8901 (2)	0.5120 (2)	0.0568 (7)
H8	0.6906	0.8537	0.4584	0.068*
C9	0.8016 (3)	1.0192 (3)	0.5641 (3)	0.0661 (8)
H9	0.7353	1.0691	0.5462	0.079*
C10	0.9247 (3)	1.0737 (3)	0.6416 (3)	0.0691 (8)
H10	0.9423	1.1608	0.6779	0.083*
C11	1.0216 (3)	1.0016 (3)	0.6661 (3)	0.0770 (9)
H11	1.1063	1.0395	0.7181	0.092*
C12	0.9953 (3)	0.8704 (3)	0.6138 (2)	0.0655 (8)
H12	1.0626	0.8214	0.6307	0.079*
C13	0.6338 (2)	0.1923 (2)	0.27856 (19)	0.0421 (5)
C14	0.5503 (3)	0.2301 (2)	0.3367 (2)	0.0567 (7)
H14	0.5454	0.3160	0.3624	0.068*
C15	0.4731 (3)	0.1394 (3)	0.3569 (2)	0.0700 (8)
H15	0.4168	0.1650	0.3969	0.084*
C16	0.4787 (3)	0.0121 (3)	0.3187 (2)	0.0657 (8)
H16	0.4275	−0.0482	0.3335	0.079*
C17	0.5606 (3)	−0.0250 (2)	0.2585 (2)	0.0613 (7)
H17	0.5632	−0.1112	0.2306	0.074*
C18	0.6397 (3)	0.0644 (2)	0.2385 (2)	0.0537 (6)
H18	0.6962	0.0386	0.1986	0.064*
C19	0.7924 (2)	−0.04243 (19)	−0.08586 (19)	0.0414 (5)
C20	0.7077 (3)	−0.0968 (2)	−0.0437 (2)	0.0488 (6)
H20	0.6589	−0.0476	−0.0069	0.059*
C21	0.6971 (3)	−0.2271 (2)	−0.0578 (2)	0.0554 (7)
C22	0.7651 (3)	−0.3030 (2)	−0.1140 (2)	0.0629 (8)
H22	0.7567	−0.3900	−0.1219	0.075*
C23	0.8462 (3)	−0.2473 (2)	−0.1585 (2)	0.0628 (7)
H23	0.8912	−0.2978	−0.1989	0.075*
C24	0.8620 (3)	−0.1173 (2)	−0.1443 (2)	0.0532 (6)
H24	0.9185	−0.0804	−0.1734	0.064*
C25	0.7690 (2)	0.34949 (17)	−0.18724 (18)	0.0367 (5)
C26	0.7993 (3)	0.3826 (2)	−0.2774 (2)	0.0466 (6)
H26	0.8847	0.3840	−0.2777	0.056*
C27	0.7010 (3)	0.4132 (2)	−0.3663 (2)	0.0621 (8)
H27	0.7206	0.4345	−0.4271	0.075*
C28	0.5748 (3)	0.4127 (3)	−0.3663 (2)	0.0661 (8)
H28	0.5097	0.4340	−0.4264	0.079*
C29	0.5450 (3)	0.3804 (2)	−0.2768 (2)	0.0599 (7)
H29	0.4597	0.3804	−0.2763	0.072*
C30	0.6417 (2)	0.3480 (2)	−0.1879 (2)	0.0454 (6)
H30	0.6210	0.3250	−0.1283	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1326 (8)	0.0500 (4)	0.1256 (7)	−0.0044 (4)	0.0769 (6)	0.0270 (5)
S1	0.0814 (5)	0.0344 (3)	0.0551 (4)	−0.0089 (3)	0.0419 (4)	−0.0015 (3)
N1	0.0592 (13)	0.0348 (10)	0.0453 (11)	−0.0037 (9)	0.0270 (10)	0.0030 (9)
N2	0.0562 (13)	0.0326 (10)	0.0416 (11)	−0.0012 (9)	0.0257 (10)	0.0072 (8)
N3	0.0549 (12)	0.0273 (9)	0.0405 (10)	0.0031 (8)	0.0231 (9)	0.0092 (8)
N4	0.0485 (12)	0.0268 (9)	0.0376 (10)	0.0031 (8)	0.0220 (9)	0.0095 (8)
N5	0.0684 (15)	0.0268 (9)	0.0482 (12)	0.0058 (9)	0.0333 (11)	0.0095 (9)
N6	0.0462 (13)	0.0320 (10)	0.0425 (11)	0.0015 (9)	0.0247 (10)	0.0097 (8)
O1	0.0586 (11)	0.0292 (8)	0.0553 (10)	−0.0024 (7)	0.0322 (8)	0.0093 (7)
C1	0.0506 (15)	0.0322 (11)	0.0431 (13)	−0.0009 (10)	0.0233 (11)	0.0042 (10)
C2	0.0441 (14)	0.0295 (11)	0.0390 (12)	−0.0009 (9)	0.0190 (10)	0.0060 (9)
C3	0.0446 (14)	0.0326 (11)	0.0362 (12)	0.0020 (10)	0.0175 (10)	0.0099 (9)
C4	0.0435 (14)	0.0272 (10)	0.0385 (12)	0.0043 (9)	0.0163 (10)	0.0100 (9)
C5	0.0364 (13)	0.0297 (11)	0.0419 (12)	0.0019 (9)	0.0160 (10)	0.0078 (9)
C6	0.081 (2)	0.0429 (14)	0.0478 (15)	−0.0009 (13)	0.0318 (14)	0.0046 (11)
C7	0.0543 (16)	0.0395 (12)	0.0403 (13)	0.0015 (11)	0.0266 (12)	0.0035 (10)
C8	0.0528 (17)	0.0561 (16)	0.0603 (16)	0.0026 (13)	0.0232 (13)	0.0114 (13)
C9	0.074 (2)	0.0498 (16)	0.085 (2)	0.0168 (15)	0.0418 (18)	0.0178 (15)
C10	0.087 (2)	0.0399 (14)	0.087 (2)	−0.0006 (16)	0.0523 (19)	0.0005 (14)
C11	0.061 (2)	0.0630 (19)	0.083 (2)	−0.0084 (16)	0.0222 (17)	−0.0132 (16)
C12	0.0561 (18)	0.0586 (17)	0.0715 (19)	0.0141 (14)	0.0196 (15)	0.0030 (14)
C13	0.0484 (15)	0.0421 (12)	0.0358 (12)	−0.0045 (11)	0.0161 (11)	0.0122 (10)
C14	0.0707 (19)	0.0505 (15)	0.0511 (15)	−0.0058 (13)	0.0332 (14)	0.0051 (12)
C15	0.076 (2)	0.077 (2)	0.0628 (18)	−0.0123 (16)	0.0422 (16)	0.0110 (15)
C16	0.074 (2)	0.0634 (18)	0.0602 (17)	−0.0176 (15)	0.0256 (15)	0.0226 (14)
C17	0.077 (2)	0.0452 (14)	0.0671 (18)	−0.0042 (14)	0.0309 (16)	0.0218 (13)
C18	0.0669 (18)	0.0450 (14)	0.0590 (16)	0.0046 (12)	0.0314 (14)	0.0204 (12)
C19	0.0525 (15)	0.0284 (11)	0.0404 (13)	0.0054 (10)	0.0145 (11)	0.0079 (10)
C20	0.0653 (17)	0.0320 (12)	0.0514 (14)	0.0056 (11)	0.0260 (13)	0.0089 (11)
C21	0.0706 (19)	0.0365 (13)	0.0586 (16)	−0.0001 (12)	0.0230 (14)	0.0150 (12)
C22	0.086 (2)	0.0288 (12)	0.0727 (19)	0.0135 (13)	0.0263 (17)	0.0151 (13)
C23	0.075 (2)	0.0366 (13)	0.0789 (19)	0.0184 (13)	0.0331 (16)	0.0098 (13)
C24	0.0639 (18)	0.0365 (13)	0.0624 (16)	0.0082 (12)	0.0292 (14)	0.0103 (12)
C25	0.0520 (15)	0.0214 (10)	0.0363 (12)	0.0018 (9)	0.0186 (11)	0.0046 (9)
C26	0.0625 (17)	0.0385 (12)	0.0442 (14)	0.0022 (11)	0.0292 (13)	0.0083 (11)
C27	0.088 (2)	0.0571 (16)	0.0436 (15)	0.0016 (15)	0.0250 (15)	0.0192 (13)
C28	0.075 (2)	0.0660 (18)	0.0525 (17)	0.0097 (16)	0.0115 (15)	0.0254 (14)
C29	0.0521 (17)	0.0617 (17)	0.0612 (17)	0.0069 (13)	0.0148 (14)	0.0173 (14)
C30	0.0495 (16)	0.0426 (13)	0.0473 (14)	0.0013 (11)	0.0214 (12)	0.0140 (11)

Geometric parameters (Å, º) top

Cl1—C21	1.746 (3)	C12—H12	0.9300
S1—C1	1.748 (2)	C13—C14	1.367 (3)
S1—C6	1.816 (2)	C13—C18	1.383 (3)
N1—C1	1.318 (3)	C14—C15	1.386 (3)
N1—N2	1.397 (2)	C14—H14	0.9300
N2—C3	1.357 (3)	C15—C16	1.373 (4)
N2—C13	1.430 (3)	C15—H15	0.9300
N3—C4	1.304 (3)	C16—C17	1.369 (4)
N3—C3	1.357 (3)	C16—H16	0.9300
N4—C4	1.389 (2)	C17—C18	1.387 (3)
N4—N6	1.409 (2)	C17—H17	0.9300
N4—C5	1.420 (3)	C18—H18	0.9300
N5—C4	1.351 (3)	C19—C20	1.376 (3)
N5—C19	1.415 (3)	C19—C24	1.392 (3)
N5—H5	0.79 (2)	C20—C21	1.388 (3)
N6—C25	1.426 (3)	C20—H20	0.9300
N6—H6	0.81 (2)	C21—C22	1.369 (4)
O1—C5	1.223 (2)	C22—C23	1.375 (4)
C1—C2	1.421 (3)	C22—H22	0.9300
C2—C3	1.388 (3)	C23—C24	1.384 (3)
C2—C5	1.420 (3)	C23—H23	0.9300
C6—C7	1.508 (3)	C24—H24	0.9300
C6—H6A	0.9700	C25—C30	1.381 (3)
C6—H6B	0.9700	C25—C26	1.393 (3)
C7—C12	1.369 (4)	C26—C27	1.382 (4)
C7—C8	1.377 (3)	C26—H26	0.9300
C8—C9	1.375 (4)	C27—C28	1.372 (4)
C8—H8	0.9300	C27—H27	0.9300
C9—C10	1.357 (4)	C28—C29	1.379 (4)
C9—H9	0.9300	C28—H28	0.9300
C10—C11	1.351 (4)	C29—C30	1.382 (3)
C10—H10	0.9300	C29—H29	0.9300
C11—C12	1.396 (4)	C30—H30	0.9300
C11—H11	0.9300

C1—S1—C6	101.17 (11)	C14—C13—C18	120.3 (2)
C1—N1—N2	105.43 (17)	C14—C13—N2	119.3 (2)
C3—N2—N1	110.80 (16)	C18—C13—N2	120.4 (2)
C3—N2—C13	129.75 (18)	C13—C14—C15	119.5 (2)
N1—N2—C13	118.85 (17)	C13—C14—H14	120.2
C4—N3—C3	113.84 (17)	C15—C14—H14	120.2
C4—N4—N6	117.28 (16)	C16—C15—C14	120.9 (3)
C4—N4—C5	123.97 (17)	C16—C15—H15	119.6
N6—N4—C5	118.71 (15)	C14—C15—H15	119.6
C4—N5—C19	128.2 (2)	C17—C16—C15	119.1 (2)
C4—N5—H5	115.2 (17)	C17—C16—H16	120.4
C19—N5—H5	115.4 (17)	C15—C16—H16	120.4
N4—N6—C25	114.04 (18)	C16—C17—C18	120.8 (3)
N4—N6—H6	109.4 (15)	C16—C17—H17	119.6
C25—N6—H6	114.9 (15)	C18—C17—H17	119.6
N1—C1—C2	111.45 (18)	C13—C18—C17	119.3 (2)
N1—C1—S1	123.62 (16)	C13—C18—H18	120.4
C2—C1—S1	124.93 (16)	C17—C18—H18	120.4
C3—C2—C5	119.40 (19)	C20—C19—C24	120.6 (2)
C3—C2—C1	105.10 (18)	C20—C19—N5	123.2 (2)
C5—C2—C1	135.25 (19)	C24—C19—N5	116.2 (2)
N3—C3—N2	125.70 (18)	C19—C20—C21	118.1 (2)
N3—C3—C2	127.08 (19)	C19—C20—H20	120.9
N2—C3—C2	107.21 (18)	C21—C20—H20	120.9
N3—C4—N5	121.72 (19)	C22—C21—C20	122.6 (2)
N3—C4—N4	123.69 (19)	C22—C21—Cl1	119.16 (19)
N5—C4—N4	114.59 (19)	C20—C21—Cl1	118.2 (2)
O1—C5—C2	128.6 (2)	C21—C22—C23	118.3 (2)
O1—C5—N4	119.93 (19)	C21—C22—H22	120.9
C2—C5—N4	111.51 (17)	C23—C22—H22	120.9
C7—C6—S1	108.09 (16)	C22—C23—C24	121.1 (2)
C7—C6—H6A	110.1	C22—C23—H23	119.4
S1—C6—H6A	110.1	C24—C23—H23	119.4
C7—C6—H6B	110.1	C23—C24—C19	119.2 (2)
S1—C6—H6B	110.1	C23—C24—H24	120.4
H6A—C6—H6B	108.4	C19—C24—H24	120.4
C12—C7—C8	118.1 (2)	C30—C25—C26	119.7 (2)
C12—C7—C6	121.6 (2)	C30—C25—N6	122.8 (2)
C8—C7—C6	120.3 (2)	C26—C25—N6	117.5 (2)
C9—C8—C7	121.3 (3)	C27—C26—C25	119.2 (2)
C9—C8—H8	119.3	C27—C26—H26	120.4
C7—C8—H8	119.3	C25—C26—H26	120.4
C10—C9—C8	119.9 (3)	C28—C27—C26	121.0 (2)
C10—C9—H9	120.1	C28—C27—H27	119.5
C8—C9—H9	120.1	C26—C27—H27	119.5
C11—C10—C9	120.1 (3)	C27—C28—C29	119.8 (3)
C11—C10—H10	120.0	C27—C28—H28	120.1
C9—C10—H10	120.0	C29—C28—H28	120.1
C10—C11—C12	120.3 (3)	C28—C29—C30	120.0 (3)
C10—C11—H11	119.9	C28—C29—H29	120.0
C12—C11—H11	119.9	C30—C29—H29	120.0
C7—C12—C11	120.3 (3)	C25—C30—C29	120.3 (2)
C7—C12—H12	119.9	C25—C30—H30	119.8
C11—C12—H12	119.9	C29—C30—H30	119.8

C1—N1—N2—C3	0.7 (3)	C6—C7—C8—C9	179.4 (2)
C1—N1—N2—C13	−171.3 (2)	C7—C8—C9—C10	0.7 (4)
C4—N4—N6—C25	100.4 (2)	C8—C9—C10—C11	1.1 (4)
C5—N4—N6—C25	−77.3 (2)	C9—C10—C11—C12	−1.3 (5)
N2—N1—C1—C2	0.0 (3)	C8—C7—C12—C11	2.0 (4)
N2—N1—C1—S1	−179.17 (17)	C6—C7—C12—C11	−179.6 (2)
C6—S1—C1—N1	13.9 (2)	C10—C11—C12—C7	−0.3 (5)
C6—S1—C1—C2	−165.1 (2)	C3—N2—C13—C14	−149.5 (2)
N1—C1—C2—C3	−0.6 (3)	N1—N2—C13—C14	20.7 (3)
S1—C1—C2—C3	178.52 (17)	C3—N2—C13—C18	29.3 (4)
N1—C1—C2—C5	173.3 (2)	N1—N2—C13—C18	−160.5 (2)
S1—C1—C2—C5	−7.5 (4)	C18—C13—C14—C15	1.0 (4)
C4—N3—C3—N2	178.3 (2)	N2—C13—C14—C15	179.8 (2)
C4—N3—C3—C2	−3.2 (3)	C13—C14—C15—C16	−0.4 (4)
N1—N2—C3—N3	177.6 (2)	C14—C15—C16—C17	−0.9 (4)
C13—N2—C3—N3	−11.5 (4)	C15—C16—C17—C18	1.6 (4)
N1—N2—C3—C2	−1.1 (3)	C14—C13—C18—C17	−0.3 (4)
C13—N2—C3—C2	169.7 (2)	N2—C13—C18—C17	−179.1 (2)
C5—C2—C3—N3	7.2 (4)	C16—C17—C18—C13	−1.0 (4)
C1—C2—C3—N3	−177.7 (2)	C4—N5—C19—C20	30.2 (4)
C5—C2—C3—N2	−174.1 (2)	C4—N5—C19—C24	−152.2 (2)
C1—C2—C3—N2	1.0 (3)	C24—C19—C20—C21	2.0 (4)
C3—N3—C4—N5	176.6 (2)	N5—C19—C20—C21	179.5 (2)
C3—N3—C4—N4	−3.8 (3)	C19—C20—C21—C22	−1.5 (4)
C19—N5—C4—N3	−9.2 (4)	C19—C20—C21—Cl1	−179.75 (19)
C19—N5—C4—N4	171.1 (2)	C20—C21—C22—C23	−0.4 (4)
N6—N4—C4—N3	−170.6 (2)	Cl1—C21—C22—C23	177.8 (2)
C5—N4—C4—N3	6.9 (3)	C21—C22—C23—C24	1.8 (4)
N6—N4—C4—N5	9.1 (3)	C22—C23—C24—C19	−1.3 (4)
C5—N4—C4—N5	−173.4 (2)	C20—C19—C24—C23	−0.7 (4)
C3—C2—C5—O1	175.9 (2)	N5—C19—C24—C23	−178.3 (2)
C1—C2—C5—O1	2.6 (5)	N4—N6—C25—C30	−15.6 (3)
C3—C2—C5—N4	−3.7 (3)	N4—N6—C25—C26	167.26 (17)
C1—C2—C5—N4	−177.0 (2)	C30—C25—C26—C27	−0.1 (3)
C4—N4—C5—O1	177.8 (2)	N6—C25—C26—C27	177.1 (2)
N6—N4—C5—O1	−4.7 (3)	C25—C26—C27—C28	0.6 (4)
C4—N4—C5—C2	−2.6 (3)	C26—C27—C28—C29	−0.4 (4)
N6—N4—C5—C2	174.89 (19)	C27—C28—C29—C30	−0.4 (4)
C1—S1—C6—C7	−175.34 (19)	C26—C25—C30—C29	−0.7 (3)
S1—C6—C7—C12	−96.8 (3)	N6—C25—C30—C29	−177.8 (2)
S1—C6—C7—C8	81.5 (3)	C28—C29—C30—C25	0.9 (4)
C12—C7—C8—C9	−2.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Experimental details

Crystal data
Chemical formula	C₃₀H₂₃ClN₆OS
M_r	551.05
Crystal system, space group	Triclinic, 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)
V (Å³)	1344.7 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.42 × 0.40 × 0.36

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker 2000)
T_min, T_max	0.771, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7799, 5440, 3418
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.114, 1.01
No. of reflections	5440
No. of parameters	360
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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.

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

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. CSD CrossRef Web of Science Google Scholar
Ballell, L., Field, R. A., Chung, G. A. C. & Young, R. J. (2007). Bioorg. Med. Chem. Lett. 17, 1736–1740. Web of Science CrossRef PubMed CAS Google Scholar
Bendich, A., Russell, P. J. & Fox, J. J. (1954). J. Am. Chem. Soc. 76, 6073–6077. CrossRef CAS Web of Science Google Scholar
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Holla, B. S., Mahalinga, M., Karthikeyan, M. S., Akberali, P. M. & Shetty, N. S. (2006). Bioorg. Med. Chem. 14, 2040–2047. Web of Science CrossRef PubMed CAS Google Scholar
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. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, H. Q., Liu, Z. J. & Ding, M. W. (2004). Chin. J. Struct. Chem. 23, 1133–1137. CAS Google Scholar
Wang, H. Q., Zhou, W. P., Wang, Y. Y. & Lin, C. R. (2008). J. Agric. Food Chem. 56, 7321–7325. Web of Science CSD CrossRef PubMed CAS Google Scholar

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

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