3-[(2-Chloro­thia­zol-5-yl)meth­yl]-5-(iso­butyl­amino)-6-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one

Xiao, L.-X.; Shi, D.-Q.

doi:10.1107/S1600536807021484

3-[(2-Chlorothiazol-5-yl)methyl]-5-(isobutylamino)-6-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one

The title compound, C₁₈H₁₈ClN₇OS, the mean plane of the triazolopyrimidine system makes dihedral angles of 77.54 (13) and 80.15 (13)°, respectively, with the attached phenyl and 2-chlorothiazole rings. The crystal packing is stabilized by intermolecular N—H

N hydrogen bonds and weak π–π stacking interactions [the interplanar distance is 3.724 (2) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021484/sj2311sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021484/sj2311Isup2.hkl Contains datablock I

CCDC reference: 651400

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Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
R factor = 0.064
wR factor = 0.143
Data-to-parameter ratio = 17.0

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No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.24 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.14 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

8-aza analogues of similarly substituted purines ([1,2,3]triazolo[4,5-d]pyrimidines are one such example) have been synthesized in recent years, and many of them exhibit broad spectral biological activities, such as the interesting antifungal (Roblin et al., 1945), antiviral (Shealy et al., 1984), anticancer (Kidder et al., 1951) and antiallergic (Lunt, 1982) activities. Recently, we have developed a versatile method via tandem aza-Wittig, followed by the cyclization to synthesize the novel triazolo[4,5-d]-pyrimidine derivatives (Ding et al., 2004; Wang et al., 2004). In this paper, we report the structure of the title compound, (I) (Fig. 1). In the triazolopyrimidine ring, the C5—N2, C5—N6, C6—N4, C7—N5 and C8—N5 bonds, Tabel 1, are significantly shorter than a normal single C—N bond (1.47 Å; Sasada, 1984) and closer to the value for a C═N bond (1.28 Å; Wang et al., 1998). This indicates significant electron delocalization in the triazolo[4,5-d]pyrimidinyl system.

In the crystal structure, intermolecular N—H···N hydrogen-bonds contribute strongly to the stability of the molecular configuration (Fig.2 and Table 1). In addition, short intermolecular distances between the centroids of the C1–C2/N1/S1 ring (Cg1) and the C13–C18 ring (Cg4) of the adjacent molecule indicate the existence of weak π— π stacking interactions [Cg1···Cg4i =3.7237 (20) Å, dihedral angles of 5.94 (16)°, and a shortest interplanar distance of 3.388 Å.; symmetry code: (i) 1/2 + x, -1/2 + y, z.

Related literature top

For biological activities of 8-aza purines, see: Roblin et al. (1945); Shealy et al. (1984); Kidder et al. (1951); Lunt (1982). For the synthesis of triazolopyrimidine compounds, see: Ding et al. (2004); Wang et al. (2004).

For related literature, see: Sasada (1984); Wang et al. (1998).

Experimental top

To a suspension of ethyl 1-((2-chlorothiazol-5-yl)methyl)- 5-((isobutylamino)(phenyl)methyleneamino)-1H-1,2,3-triazole-4-carboxylate (0.92 g, 2 mmol) in 10 ml of anhydrous ethanol, several drops of EtONa in EtOH were added at room temperature. The mixture was stirred for 10 min (monitored by thin layer chromatography), then the solution concentrated under vacuum and the residue was recrystallized from dichloromethane to give the title compound (yield 76%). Colourless crystals of (I) suitable for X-ray structure analysis were grown from a mixture of dichloromethane and ethanol (v/v, 1:3).

Structure description top

For related literature, see: Sasada (1984); Wang et al. (1998).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Crystal packing diagram of (I). Hydrogen bonds are shown as dashed lines.

3-[(2-Chlorothiazol-5-yl)methyl]-5-(isobutylamino)-6-phenyl-3H- 1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one top

Crystal data top

C₁₈H₁₈ClN₇OS	F(000) = 1728
M_r = 415.90	D_x = 1.380 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1064 reflections
a = 20.0916 (18) Å	θ = 2.8–16.5°
b = 7.2538 (7) Å	µ = 0.32 mm⁻¹
c = 28.046 (2) Å	T = 294 K
β = 101.527 (2)°	Block, colorless
V = 4005.0 (6) Å³	0.20 × 0.10 × 0.04 mm
Z = 8

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4343 independent reflections
Radiation source: fine-focus sealed tube	2226 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.096
φ and ω scans	θ_max = 27.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −25→25
T_min = 0.939, T_max = 0.987	k = −9→9
17095 measured reflections	l = −33→35

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0523P)²] where P = (F_o² + 2F_c²)/3
4343 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₈H₁₈ClN₇OS	V = 4005.0 (6) Å³
M_r = 415.90	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.0916 (18) Å	µ = 0.32 mm⁻¹
b = 7.2538 (7) Å	T = 294 K
c = 28.046 (2) Å	0.20 × 0.10 × 0.04 mm
β = 101.527 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4343 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	2226 reflections with I > 2σ(I)
T_min = 0.939, T_max = 0.987	R_int = 0.096
17095 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 0.98	Δρ_max = 0.28 e Å⁻³
4343 reflections	Δρ_min = −0.25 e Å⁻³
255 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
C1	0.45437 (18)	−0.1881 (5)	0.07899 (12)	0.0475 (9)
C2	0.49843 (16)	−0.1194 (5)	0.15347 (12)	0.0456 (9)
H2	0.5333	−0.1040	0.1805	0.055*
C3	0.43344 (15)	−0.0848 (4)	0.15564 (11)	0.0357 (8)
C4	0.40458 (15)	−0.0225 (5)	0.19814 (11)	0.0431 (9)
H4A	0.4402	−0.0224	0.2271	0.052*
H4B	0.3880	0.1027	0.1925	0.052*
C5	0.28245 (15)	−0.1132 (4)	0.19072 (10)	0.0331 (7)
C6	0.25197 (16)	−0.2612 (4)	0.20799 (11)	0.0383 (8)
C7	0.17957 (17)	−0.2757 (5)	0.19767 (11)	0.0387 (8)
C8	0.18729 (16)	0.0218 (4)	0.15449 (11)	0.0351 (8)
C9	0.18402 (17)	0.3310 (4)	0.11911 (13)	0.0482 (9)
H9A	0.2218	0.3564	0.1457	0.058*
H9B	0.1518	0.4312	0.1179	0.058*
C10	0.2099 (2)	0.3308 (6)	0.07249 (15)	0.0692 (12)
H10	0.2472	0.2415	0.0757	0.083*
C11	0.1566 (3)	0.2773 (7)	0.02910 (14)	0.1029 (17)
H11A	0.1441	0.1508	0.0321	0.154*
H11B	0.1743	0.2926	0.0000	0.154*
H11C	0.1174	0.3544	0.0275	0.154*
C12	0.2385 (2)	0.5219 (6)	0.06524 (18)	0.1065 (18)
H12A	0.2028	0.6118	0.0623	0.160*
H12B	0.2569	0.5222	0.0362	0.160*
H12C	0.2737	0.5517	0.0927	0.160*
C13	0.07716 (15)	−0.1286 (4)	0.15216 (11)	0.0341 (7)
C14	0.04907 (17)	−0.1883 (5)	0.10585 (11)	0.0461 (9)
H14	0.0768	−0.2274	0.0850	0.055*
C15	−0.02078 (19)	−0.1895 (5)	0.09071 (13)	0.0563 (10)
H15	−0.0401	−0.2282	0.0594	0.068*
C16	−0.06186 (18)	−0.1337 (5)	0.12179 (15)	0.0555 (10)
H16	−0.1088	−0.1348	0.1114	0.067*
C17	−0.03405 (18)	−0.0767 (5)	0.16788 (14)	0.0544 (10)
H17	−0.0621	−0.0401	0.1888	0.065*
C18	0.03624 (17)	−0.0733 (4)	0.18352 (12)	0.0446 (9)
H18	0.0554	−0.0341	0.2148	0.054*
Cl1	0.44869 (6)	−0.26117 (17)	0.02014 (3)	0.0838 (4)
N1	0.51130 (14)	−0.1786 (4)	0.10948 (10)	0.0489 (8)
N2	0.34916 (12)	−0.1415 (4)	0.20609 (9)	0.0375 (7)
N3	0.36005 (14)	−0.3031 (4)	0.23214 (9)	0.0474 (7)
N4	0.30135 (14)	−0.3749 (4)	0.23363 (9)	0.0488 (8)
N5	0.15024 (12)	−0.1259 (3)	0.16775 (8)	0.0361 (6)
N6	0.25402 (12)	0.0313 (4)	0.16422 (9)	0.0368 (7)
N7	0.15143 (13)	0.1615 (4)	0.13001 (9)	0.0426 (7)
H7	0.1082	0.1501	0.1206	0.051*
O1	0.14303 (12)	−0.3936 (3)	0.20981 (8)	0.0531 (7)
S1	0.38275 (4)	−0.12598 (13)	0.09935 (3)	0.0491 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.052 (2)	0.052 (2)	0.0397 (19)	0.0035 (19)	0.0133 (17)	−0.0012 (17)
C2	0.035 (2)	0.055 (2)	0.045 (2)	−0.0009 (18)	0.0037 (15)	−0.0014 (18)
C3	0.0272 (18)	0.042 (2)	0.0372 (18)	0.0041 (15)	0.0038 (14)	0.0002 (15)
C4	0.0303 (19)	0.056 (2)	0.044 (2)	−0.0006 (17)	0.0084 (15)	−0.0054 (17)
C5	0.0321 (18)	0.040 (2)	0.0281 (16)	0.0018 (16)	0.0090 (13)	−0.0037 (15)
C6	0.037 (2)	0.043 (2)	0.0369 (18)	0.0012 (17)	0.0103 (15)	0.0050 (16)
C7	0.042 (2)	0.044 (2)	0.0312 (17)	−0.0009 (18)	0.0085 (15)	0.0017 (16)
C8	0.0321 (19)	0.039 (2)	0.0348 (18)	0.0020 (16)	0.0086 (14)	0.0011 (15)
C9	0.041 (2)	0.033 (2)	0.068 (2)	0.0025 (16)	0.0060 (18)	0.0090 (18)
C10	0.062 (3)	0.068 (3)	0.080 (3)	−0.002 (2)	0.020 (2)	0.023 (2)
C11	0.114 (4)	0.131 (5)	0.061 (3)	−0.028 (3)	0.010 (3)	0.007 (3)
C12	0.106 (4)	0.087 (4)	0.138 (5)	−0.027 (3)	0.052 (3)	0.033 (3)
C13	0.0316 (18)	0.0351 (19)	0.0353 (18)	−0.0028 (15)	0.0061 (14)	0.0012 (15)
C14	0.043 (2)	0.055 (2)	0.0396 (19)	−0.0017 (18)	0.0068 (16)	−0.0028 (17)
C15	0.050 (2)	0.064 (3)	0.048 (2)	−0.009 (2)	−0.0092 (19)	0.005 (2)
C16	0.033 (2)	0.053 (2)	0.076 (3)	−0.0008 (19)	0.001 (2)	0.011 (2)
C17	0.040 (2)	0.053 (2)	0.074 (3)	−0.0021 (18)	0.022 (2)	−0.003 (2)
C18	0.042 (2)	0.051 (2)	0.0417 (19)	−0.0083 (17)	0.0088 (16)	−0.0063 (16)
Cl1	0.0986 (9)	0.1105 (10)	0.0437 (6)	0.0133 (7)	0.0175 (6)	−0.0084 (6)
N1	0.0382 (17)	0.060 (2)	0.0487 (18)	0.0021 (15)	0.0101 (14)	0.0000 (16)
N2	0.0318 (15)	0.0440 (17)	0.0366 (15)	0.0012 (13)	0.0068 (12)	0.0025 (13)
N3	0.0419 (18)	0.0529 (19)	0.0474 (17)	0.0120 (15)	0.0090 (14)	0.0155 (15)
N4	0.0411 (18)	0.0506 (19)	0.0550 (18)	0.0101 (15)	0.0105 (14)	0.0185 (15)
N5	0.0287 (14)	0.0424 (16)	0.0371 (15)	−0.0021 (13)	0.0064 (11)	0.0050 (13)
N6	0.0289 (16)	0.0404 (16)	0.0414 (15)	0.0008 (13)	0.0075 (12)	0.0079 (13)
N7	0.0259 (14)	0.0418 (17)	0.0584 (17)	−0.0007 (13)	0.0042 (13)	0.0138 (14)
O1	0.0468 (15)	0.0507 (16)	0.0617 (16)	−0.0091 (13)	0.0108 (12)	0.0176 (13)
S1	0.0348 (5)	0.0655 (7)	0.0443 (5)	0.0008 (5)	0.0014 (4)	−0.0024 (5)

Geometric parameters (Å, º) top

C1—N1	1.286 (4)	C10—C11	1.503 (5)
C1—S1	1.711 (4)	C10—C12	1.529 (5)
C1—Cl1	1.715 (3)	C10—H10	0.9800
C2—C3	1.343 (4)	C11—H11A	0.9600
C2—N1	1.379 (4)	C11—H11B	0.9600
C2—H2	0.9300	C11—H11C	0.9600
C3—C4	1.496 (4)	C12—H12A	0.9600
C3—S1	1.725 (3)	C12—H12B	0.9600
C4—N2	1.460 (4)	C12—H12C	0.9600
C4—H4A	0.9700	C13—C18	1.378 (4)
C4—H4B	0.9700	C13—C14	1.378 (4)
C5—N2	1.339 (4)	C13—N5	1.446 (4)
C5—N6	1.344 (4)	C14—C15	1.383 (4)
C5—C6	1.372 (4)	C14—H14	0.9300
C6—N4	1.377 (4)	C15—C16	1.375 (5)
C6—C7	1.429 (4)	C15—H15	0.9300
C7—O1	1.219 (3)	C16—C17	1.366 (5)
C7—N5	1.426 (4)	C16—H16	0.9300
C8—N6	1.316 (4)	C17—C18	1.393 (4)
C8—N7	1.349 (4)	C17—H17	0.9300
C8—N5	1.397 (4)	C18—H18	0.9300
C9—N7	1.454 (4)	N2—N3	1.376 (3)
C9—C10	1.501 (5)	N3—N4	1.298 (3)
C9—H9A	0.9700	N7—H7	0.8600
C9—H9B	0.9700

N1—C1—S1	117.4 (3)	C10—C11—H11C	109.5
N1—C1—Cl1	122.4 (3)	H11A—C11—H11C	109.5
S1—C1—Cl1	120.3 (2)	H11B—C11—H11C	109.5
C3—C2—N1	117.2 (3)	C10—C12—H12A	109.5
C3—C2—H2	121.4	C10—C12—H12B	109.5
N1—C2—H2	121.4	H12A—C12—H12B	109.5
C2—C3—C4	128.9 (3)	C10—C12—H12C	109.5
C2—C3—S1	109.1 (2)	H12A—C12—H12C	109.5
C4—C3—S1	122.0 (2)	H12B—C12—H12C	109.5
N2—C4—C3	111.8 (3)	C18—C13—C14	120.6 (3)
N2—C4—H4A	109.2	C18—C13—N5	120.2 (3)
C3—C4—H4A	109.2	C14—C13—N5	119.3 (3)
N2—C4—H4B	109.2	C13—C14—C15	119.4 (3)
C3—C4—H4B	109.2	C13—C14—H14	120.3
H4A—C4—H4B	107.9	C15—C14—H14	120.3
N2—C5—N6	125.8 (3)	C16—C15—C14	120.3 (3)
N2—C5—C6	104.8 (3)	C16—C15—H15	119.9
N6—C5—C6	129.4 (3)	C14—C15—H15	119.9
C5—C6—N4	109.1 (3)	C17—C16—C15	120.3 (3)
C5—C6—C7	119.6 (3)	C17—C16—H16	119.8
N4—C6—C7	131.3 (3)	C15—C16—H16	119.8
O1—C7—N5	119.8 (3)	C16—C17—C18	120.1 (3)
O1—C7—C6	129.8 (3)	C16—C17—H17	120.0
N5—C7—C6	110.3 (3)	C18—C17—H17	120.0
N6—C8—N7	119.0 (3)	C13—C18—C17	119.4 (3)
N6—C8—N5	124.1 (3)	C13—C18—H18	120.3
N7—C8—N5	116.9 (3)	C17—C18—H18	120.3
N7—C9—C10	115.6 (3)	C1—N1—C2	108.1 (3)
N7—C9—H9A	108.4	C5—N2—N3	110.1 (3)
C10—C9—H9A	108.4	C5—N2—C4	127.2 (3)
N7—C9—H9B	108.4	N3—N2—C4	122.6 (3)
C10—C9—H9B	108.4	N4—N3—N2	108.1 (2)
H9A—C9—H9B	107.4	N3—N4—C6	107.9 (3)
C9—C10—C11	113.0 (3)	C8—N5—C7	124.1 (3)
C9—C10—C12	108.6 (4)	C8—N5—C13	119.5 (2)
C11—C10—C12	110.6 (4)	C7—N5—C13	116.3 (2)
C9—C10—H10	108.2	C8—N6—C5	112.1 (3)
C11—C10—H10	108.2	C8—N7—C9	121.7 (3)
C12—C10—H10	108.2	C8—N7—H7	119.2
C10—C11—H11A	109.5	C9—N7—H7	119.2
C10—C11—H11B	109.5	C1—S1—C3	88.22 (16)
H11A—C11—H11B	109.5

N1—C2—C3—C4	179.0 (3)	C3—C4—N2—N3	84.1 (3)
N1—C2—C3—S1	−0.4 (4)	C5—N2—N3—N4	−0.6 (3)
C2—C3—C4—N2	−127.6 (3)	C4—N2—N3—N4	178.7 (3)
S1—C3—C4—N2	51.7 (4)	N2—N3—N4—C6	0.7 (3)
N2—C5—C6—N4	0.3 (3)	C5—C6—N4—N3	−0.6 (4)
N6—C5—C6—N4	−179.7 (3)	C7—C6—N4—N3	179.1 (3)
N2—C5—C6—C7	−179.5 (3)	N6—C8—N5—C7	6.6 (5)
N6—C5—C6—C7	0.5 (5)	N7—C8—N5—C7	−173.7 (3)
C5—C6—C7—O1	−179.3 (3)	N6—C8—N5—C13	−175.5 (3)
N4—C6—C7—O1	1.0 (6)	N7—C8—N5—C13	4.2 (4)
C5—C6—C7—N5	2.1 (4)	O1—C7—N5—C8	175.8 (3)
N4—C6—C7—N5	−177.6 (3)	C6—C7—N5—C8	−5.5 (4)
N7—C9—C10—C11	53.4 (5)	O1—C7—N5—C13	−2.1 (4)
N7—C9—C10—C12	176.6 (3)	C6—C7—N5—C13	176.7 (3)
C18—C13—C14—C15	1.1 (5)	C18—C13—N5—C8	−98.9 (3)
N5—C13—C14—C15	−179.5 (3)	C14—C13—N5—C8	81.6 (4)
C13—C14—C15—C16	−0.8 (5)	C18—C13—N5—C7	79.0 (4)
C14—C15—C16—C17	0.0 (6)	C14—C13—N5—C7	−100.4 (3)
C15—C16—C17—C18	0.5 (5)	N7—C8—N6—C5	177.0 (3)
C14—C13—C18—C17	−0.5 (5)	N5—C8—N6—C5	−3.3 (4)
N5—C13—C18—C17	180.0 (3)	N2—C5—N6—C8	179.9 (3)
C16—C17—C18—C13	−0.3 (5)	C6—C5—N6—C8	−0.1 (4)
S1—C1—N1—C2	0.9 (4)	N6—C8—N7—C9	−7.2 (5)
Cl1—C1—N1—C2	−178.7 (3)	N5—C8—N7—C9	173.1 (3)
C3—C2—N1—C1	−0.3 (4)	C10—C9—N7—C8	88.0 (4)
N6—C5—N2—N3	−179.9 (3)	N1—C1—S1—C3	−1.0 (3)
C6—C5—N2—N3	0.2 (3)	Cl1—C1—S1—C3	178.6 (2)
N6—C5—N2—C4	0.9 (5)	C2—C3—S1—C1	0.7 (3)
C6—C5—N2—C4	−179.1 (3)	C4—C3—S1—C1	−178.8 (3)
C3—C4—N2—C5	−96.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···N1ⁱ	0.86	2.28	2.993 (4)	141

Symmetry code: (i) x−1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈ClN₇OS
M_r	415.90
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	294
a, b, c (Å)	20.0916 (18), 7.2538 (7), 28.046 (2)
β (°)	101.527 (2)
V (Å³)	4005.0 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.20 × 0.10 × 0.04

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.939, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	17095, 4343, 2226
R_int	0.096
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.143, 0.98
No. of reflections	4343
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.25

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Selected bond lengths (Å) top

C5—N6	1.344 (4)	C8—N5	1.397 (4)
C6—N4	1.377 (4)	C9—N7	1.454 (4)
C7—N5	1.426 (4)	C13—N5	1.446 (4)
C8—N6	1.316 (4)	N2—N3	1.376 (3)
C8—N7	1.349 (4)	N3—N4	1.298 (3)