5-[(4,6-Dimethyl­pyrimidin-2-ylsulfanyl)meth­yl]-3-(morpholinometh­yl)-1,3,4-oxadiazole-2(3H)-thione

Thiruvalluvar, A.; Subramanyam, M.; Lingappa, B.; Kalluraya, B.

doi:10.1107/S1600536807032448

5-[(4,6-Dimethylpyrimidin-2-ylsulfanyl)methyl]-3-(morpholinomethyl)-1,3,4-oxadiazole-2(3H)-thione

A. Thiruvalluvar, M. Subramanyam, B. Lingappa and B. Kalluraya

In the title compound, C₁₄H₁₉N₅O₂S₂, the pyrimidine ring makes a dihedral angle of 82.8 (1)° with the oxadiazole ring. The morpholine ring adopts a chair conformation. There is a short intermolecular contact between the morpholine O atom and the sulfanylmethyl C atom [2.938 (3) Å]. The molecules are linked by C—H

S hydrogen bonds. An intramolecular C—H

N hydrogen bond is also present.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032448/wn2165sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032448/wn2165Isup2.hkl Contains datablock I

CCDC reference: 657708

checkCIF report

Key indicators

Single-crystal X-ray study
T = 160 K
Mean (C-C) = 0.004 Å
R factor = 0.057
wR factor = 0.177
Data-to-parameter ratio = 24.7

checkCIF/PLATON results

No syntax errors found



Alert level B
DIFMX01_ALERT_2_B  The maximum difference density is > 0.1*ZMAX*1.00
            _refine_diff_density_max given =      1.981
            Test value =      1.600
PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density ....       4.76
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............       1.98 e/A   

Alert level C
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O21    ..  C2      ..       2.94 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      82.00 A   3 

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

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

Comment top

A literature survey shows that large numbers of simple, N-bridged, nitrogen- and sulfur-containing heterocyclic compounds containing the pyrimidine unit have diverse biological activities (Wichmann et al., 1999; El-Bendary et al., 1998; Kirpal, 1999; Tsuji & Ishikawa, 1994). In the light of this significant importance of pyrimidine compounds, and as a continuation of our work on the study of pyrimidine derivatives (Thiruvalluvaret al., 2007a,b), an X-ray crystallographic structure determination of the title compound was undertaken and the results are presented here.

In the title compound, Fig.1, the pyrimidine ring makes a dihedral angle of 82.8 (1)° with the oxadiazole ring. The morpholine ring adopts a chair conformation. There is a short intermolecular contact between O21 and C2 [2.938 (3) Å; -x, -y, -z + 1]. The molecules are linked by C—H···S hydrogen bonds (Fig. 2); an intramolecular C—H···N hydrogen bond is also present.

Related literature top

For related literature, see: Wichmann et al. (1999); El-Bendary et al. (1998); Kirpal (1999); Tsuji & Ishikawa (1994); Mohan et al. (1989); Baraldi et al. (1996, 2003); Sanjay et al. (2006); Thiruvalluvar, Subramanyam, Kalluraya & Lingappa (2007); Thiruvalluvar, Subramanyam, Lingappa & Kalluraya (2007).

Experimental top

A solution of 5-(4,6-dimethyl-2-thiomethyl pyrimidyl)-1,3,4-oxadiazole-2-thione (2.56 g, 0.01 mol) in absolute ethanol (20 ml) was placed in a round-bottomed flask and treated with formaldehyde (40%, 3.0 ml). Later, morpholine (0.87 g, 0.01 mol) in ethanol (10 ml) was added with stirring and the reaction mixture was stirred overnight. The precipitated yellow solid was collected by filtration, dried and recrystallized from chloroform to give white crystals (1.64 g, 46%).

Structure description top

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The packing of the title compound, viewed down the c axis. Dashed lines indicate hydrogen bonds.

5-[(4,6-Dimethylpyrimidin-2-ylsulfanyl)methyl]-3-(morpholinomethyl)-1,3,4- oxadiazole-2(3H)-thione top

Crystal data top

C₁₄H₁₉N₅O₂S₂	Z = 2
M_r = 353.48	F(000) = 372
Triclinic, P1	D_x = 1.311 Mg m⁻³
Hall symbol: -P 1	Melting point: 378(1) K
a = 7.1250 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6735 (3) Å	Cell parameters from 32939 reflections
c = 12.3740 (5) Å	θ = 2.0–30.0°
α = 93.607 (2)°	µ = 0.31 mm⁻¹
β = 90.561 (2)°	T = 160 K
γ = 107.474 (2)°	Block, light_brown
V = 895.42 (6) Å³	0.28 × 0.23 × 0.20 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	5188 independent reflections
Radiation source: Nonius FR590 sealed tube generator	3963 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	R_int = 0.062
Detector resolution: 9 pixels mm^-1	θ_max = 30.0°, θ_min = 2.0°
φ and ω scans with κ offsets	h = −10→10
Absorption correction: multi-scan (Blessing, 1995)	k = −15→15
T_min = 0.892, T_max = 0.964	l = −17→17
25642 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.177	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0975P)² + 0.7899P] where P = (F_o² + 2F_c²)/3
5188 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 1.98 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₄H₁₉N₅O₂S₂	γ = 107.474 (2)°
M_r = 353.48	V = 895.42 (6) Å³
Triclinic, P1	Z = 2
a = 7.1250 (3) Å	Mo Kα radiation
b = 10.6735 (3) Å	µ = 0.31 mm⁻¹
c = 12.3740 (5) Å	T = 160 K
α = 93.607 (2)°	0.28 × 0.23 × 0.20 mm
β = 90.561 (2)°

Data collection top

Nonius KappaCCD area-detector diffractometer	5188 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	3963 reflections with I > 2σ(I)
T_min = 0.892, T_max = 0.964	R_int = 0.062
25642 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.177	H-atom parameters constrained
S = 1.06	Δρ_max = 1.98 e Å⁻³
5188 reflections	Δρ_min = −0.42 e Å⁻³
210 parameters

Special details top

Experimental. Solvent used: Chloroform Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 1.041 (2) Frames collected: 408 Seconds exposure per frame: 44 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 32.0

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
S5	0.62058 (8)	0.31119 (6)	0.52324 (5)	0.02696 (16)
S21	0.20019 (9)	0.59892 (5)	0.76795 (4)	0.02255 (15)
O1	0.3493 (2)	0.38961 (15)	0.63170 (13)	0.0208 (3)
O21	−0.0632 (3)	−0.12209 (17)	0.34104 (17)	0.0383 (5)
N3	0.1046 (3)	0.36310 (18)	0.51156 (15)	0.0197 (4)
N4	0.2574 (3)	0.32370 (17)	0.46596 (14)	0.0186 (4)
N11	0.3236 (3)	0.65029 (19)	0.96765 (15)	0.0222 (4)
N13	0.1632 (3)	0.42186 (19)	0.91862 (15)	0.0229 (4)
N24	0.1471 (3)	0.14660 (18)	0.32052 (15)	0.0222 (4)
C2	0.1660 (3)	0.3999 (2)	0.60967 (17)	0.0190 (4)
C4	0.2486 (3)	0.2826 (2)	0.34962 (17)	0.0216 (4)
H4A	0.1837	0.3370	0.3103	0.026*
H4B	0.3849	0.3022	0.3241	0.026*
C5	0.4063 (3)	0.3393 (2)	0.53748 (18)	0.0197 (4)
C12	0.2297 (3)	0.5477 (2)	0.89887 (18)	0.0201 (4)
C14	0.1957 (3)	0.3923 (2)	1.02001 (19)	0.0249 (5)
C15	0.2942 (4)	0.4908 (3)	1.09725 (19)	0.0264 (5)
H15	0.3198	0.4700	1.1683	0.032*
C16	0.3544 (3)	0.6198 (2)	1.06892 (19)	0.0248 (5)
C21	0.0579 (3)	0.4458 (2)	0.69701 (19)	0.0240 (5)
H21A	0.0182	0.3772	0.7497	0.029*
H21B	−0.0634	0.4576	0.6656	0.029*
C22	0.1393 (5)	−0.0825 (3)	0.3129 (3)	0.0404 (7)
H22A	0.1482	−0.0860	0.2330	0.048*
H22B	0.2040	−0.1448	0.3405	0.048*
C23	0.2460 (4)	0.0553 (2)	0.3594 (2)	0.0291 (5)
H23A	0.2458	0.0582	0.4395	0.035*
H23B	0.3845	0.0812	0.3367	0.035*
C25	−0.0601 (4)	0.1057 (2)	0.3506 (2)	0.0279 (5)
H25A	−0.1274	0.1662	0.3224	0.033*
H25B	−0.0688	0.1093	0.4305	0.033*
C26	−0.1592 (4)	−0.0334 (2)	0.3035 (2)	0.0363 (6)
H26A	−0.2986	−0.0615	0.3245	0.044*
H26B	−0.1564	−0.0354	0.2235	0.044*
C41	0.1210 (5)	0.2502 (3)	1.0433 (2)	0.0370 (6)
H41A	−0.0183	0.2282	1.0612	0.056*
H41B	0.1967	0.2341	1.1046	0.056*
H41C	0.1356	0.1953	0.9794	0.056*
C61	0.4595 (4)	0.7317 (3)	1.1477 (2)	0.0331 (6)
H61A	0.5980	0.7349	1.1552	0.050*
H61B	0.3981	0.7189	1.2183	0.050*
H61C	0.4512	0.8146	1.1213	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S5	0.0179 (3)	0.0328 (3)	0.0311 (3)	0.0095 (2)	−0.0032 (2)	0.0001 (2)
S21	0.0281 (3)	0.0208 (3)	0.0185 (3)	0.0072 (2)	−0.0025 (2)	0.0004 (2)
O1	0.0184 (7)	0.0226 (8)	0.0208 (7)	0.0057 (6)	−0.0044 (6)	−0.0001 (6)
O21	0.0448 (12)	0.0190 (8)	0.0464 (12)	0.0026 (8)	−0.0080 (9)	0.0037 (8)
N3	0.0181 (9)	0.0188 (8)	0.0221 (9)	0.0058 (7)	−0.0028 (7)	−0.0006 (7)
N4	0.0172 (8)	0.0188 (8)	0.0190 (8)	0.0049 (7)	−0.0022 (7)	−0.0005 (7)
N11	0.0217 (9)	0.0246 (9)	0.0206 (9)	0.0079 (7)	−0.0019 (7)	−0.0015 (7)
N13	0.0237 (9)	0.0229 (9)	0.0230 (9)	0.0079 (8)	0.0014 (7)	0.0025 (7)
N24	0.0278 (10)	0.0179 (9)	0.0186 (9)	0.0040 (7)	−0.0031 (7)	0.0004 (7)
C2	0.0171 (9)	0.0181 (9)	0.0206 (10)	0.0036 (8)	−0.0042 (7)	0.0016 (8)
C4	0.0261 (11)	0.0197 (10)	0.0168 (10)	0.0034 (8)	−0.0007 (8)	0.0032 (8)
C5	0.0189 (10)	0.0161 (9)	0.0220 (10)	0.0020 (7)	−0.0031 (8)	0.0021 (8)
C12	0.0172 (10)	0.0226 (10)	0.0214 (10)	0.0079 (8)	0.0001 (8)	0.0002 (8)
C14	0.0248 (11)	0.0284 (11)	0.0248 (11)	0.0122 (9)	0.0051 (9)	0.0048 (9)
C15	0.0274 (12)	0.0357 (13)	0.0186 (10)	0.0131 (10)	0.0014 (8)	0.0037 (9)
C16	0.0221 (11)	0.0312 (12)	0.0221 (11)	0.0103 (9)	−0.0010 (8)	−0.0029 (9)
C21	0.0202 (10)	0.0269 (11)	0.0230 (11)	0.0052 (9)	−0.0024 (8)	−0.0031 (9)
C22	0.0482 (17)	0.0235 (12)	0.0502 (17)	0.0136 (12)	−0.0034 (13)	−0.0040 (11)
C23	0.0299 (12)	0.0226 (11)	0.0357 (13)	0.0094 (9)	−0.0021 (10)	0.0011 (9)
C25	0.0254 (12)	0.0212 (11)	0.0337 (13)	0.0024 (9)	−0.0076 (9)	0.0010 (9)
C26	0.0359 (14)	0.0227 (12)	0.0433 (15)	−0.0009 (10)	−0.0145 (12)	0.0013 (10)
C41	0.0491 (17)	0.0289 (13)	0.0345 (14)	0.0125 (12)	0.0068 (12)	0.0091 (11)
C61	0.0383 (14)	0.0373 (14)	0.0218 (12)	0.0106 (11)	−0.0063 (10)	−0.0071 (10)

Geometric parameters (Å, º) top

S5—C5	1.651 (2)	C16—C61	1.497 (4)
S21—C12	1.772 (2)	C22—C23	1.512 (4)
S21—C21	1.810 (2)	C25—C26	1.515 (4)
O1—C2	1.369 (3)	C4—H4A	0.9900
O1—C5	1.369 (3)	C4—H4B	0.9900
O21—C22	1.430 (4)	C15—H15	0.9500
O21—C26	1.421 (4)	C21—H21A	0.9900
N3—N4	1.392 (3)	C21—H21B	0.9900
N3—C2	1.283 (3)	C22—H22A	0.9900
N4—C4	1.473 (3)	C22—H22B	0.9900
N4—C5	1.339 (3)	C23—H23A	0.9900
N11—C12	1.343 (3)	C23—H23B	0.9900
N11—C16	1.347 (3)	C25—H25A	0.9900
N13—C12	1.323 (3)	C25—H25B	0.9900
N13—C14	1.347 (3)	C26—H26A	0.9900
N24—C4	1.435 (3)	C26—H26B	0.9900
N24—C23	1.464 (3)	C41—H41A	0.9800
N24—C25	1.467 (4)	C41—H41B	0.9800
C2—C21	1.476 (3)	C41—H41C	0.9800
C14—C15	1.389 (4)	C61—H61A	0.9800
C14—C41	1.497 (4)	C61—H61B	0.9800
C15—C16	1.382 (4)	C61—H61C	0.9800

S5···N3ⁱ	3.331 (2)	C23···C5	3.519 (3)
S5···C21ⁱ	3.632 (2)	C25···N3	3.197 (3)
S5···C23	3.676 (2)	C26···C61^x	3.547 (4)
S5···C2ⁱⁱ	3.521 (2)	C61···C26^xi	3.547 (4)
S5···N3ⁱⁱ	3.496 (2)	C4···H15^ix	3.0400
S21···O1	3.1542 (16)	C4···H41B^ix	3.0400
S5···H21Bⁱ	2.8400	C5···H23A	3.0400
S5···H4B	2.9500	C14···H61A^viii	3.1000
S5···H22Bⁱⁱⁱ	3.0400	C22···H21A^v	3.0500
S21···H4A^iv	3.1700	C26···H61A^x	3.0500
S21···H4Bⁱⁱ	3.0800	H4A···H15^ix	2.3600
S21···H25A^iv	2.9900	H4A···H25A	2.4200
O1···S21	3.1542 (16)	H4A···S21^iv	3.1700
O1···N4	2.155 (2)	H4A···H21B^iv	2.5800
O1···O21^v	3.010 (2)	H4B···S5	2.9500
O21···N24	2.838 (3)	H4B···H23B	2.3700
O21···O1^v	3.010 (2)	H4B···S21ⁱⁱ	3.0800
O21···N3^v	3.190 (3)	H15···C4^xii	3.0400
O21···C2^v	2.938 (3)	H15···H4A^xii	2.3600
O21···C5^v	3.274 (3)	H15···H41B	2.4800
N3···S5^vi	3.331 (2)	H15···H61B	2.5800
N3···O1	2.220 (3)	H21A···N13	2.2800
N3···N24	3.281 (3)	H21A···C22^v	3.0500
N3···C25	3.197 (3)	H21B···S5^vi	2.8400
N3···S5ⁱⁱ	3.496 (2)	H21B···H4A^iv	2.5800
N3···O21^v	3.190 (3)	H22A···H26B	2.3900
N4···O1	2.155 (2)	H22B···S5ⁱⁱⁱ	3.0400
N24···O21	2.838 (3)	H23A···N4	2.8100
N24···N3	3.281 (3)	H23A···C5	3.0400
N3···H25B	2.7400	H23A···H25B	2.4600
N4···H25B	2.7400	H23A···H25B^v	2.5300
N4···H23A	2.8100	H23B···H4B	2.3700
N11···H41A^vii	2.8800	H25A···H4A	2.4200
N13···H61A^viii	2.8400	H25A···S21^iv	2.9900
N13···H21A	2.2800	H25B···N3	2.7400
N24···H41B^ix	2.8800	H25B···N4	2.7400
C2···S5ⁱⁱ	3.521 (2)	H25B···H23A	2.4600
C2···O21^v	2.938 (3)	H25B···H23A^v	2.5300
C5···O21^v	3.274 (3)	H26B···H22A	2.3900
C5···C23	3.519 (3)	H41A···N11^vii	2.8800
C5···C5ⁱⁱ	3.476 (3)	H41B···N24^xii	2.8800
C12···C15^viii	3.538 (4)	H41B···C4^xii	3.0400
C12···C14^vii	3.428 (3)	H41B···H15	2.4800
C14···C12^vii	3.428 (3)	H41C···H61A^viii	2.5100
C14···C16^viii	3.436 (3)	H61A···C26^xi	3.0500
C15···C12^viii	3.538 (4)	H61A···N13^viii	2.8400
C16···C14^viii	3.436 (3)	H61A···C14^viii	3.1000
C21···S5^vi	3.632 (2)	H61A···H41C^viii	2.5100
C23···S5	3.676 (2)	H61B···H15	2.5800

C12—S21—C21	101.70 (10)	C14—C15—H15	121.00
C2—O1—C5	105.80 (17)	C16—C15—H15	121.00
C22—O21—C26	110.5 (2)	S21—C21—H21A	109.00
N4—N3—C2	103.32 (19)	S21—C21—H21B	109.00
N3—N4—C4	120.00 (18)	C2—C21—H21A	109.00
N3—N4—C5	111.76 (17)	C2—C21—H21B	109.00
C4—N4—C5	128.0 (2)	H21A—C21—H21B	108.00
C12—N11—C16	115.25 (19)	O21—C22—H22A	109.00
C12—N13—C14	116.15 (19)	O21—C22—H22B	109.00
C4—N24—C23	114.03 (19)	C23—C22—H22A	109.00
C4—N24—C25	113.83 (18)	C23—C22—H22B	109.00
C23—N24—C25	110.01 (18)	H22A—C22—H22B	108.00
O1—C2—N3	113.6 (2)	N24—C23—H23A	110.00
O1—C2—C21	119.51 (18)	N24—C23—H23B	110.00
N3—C2—C21	126.8 (2)	C22—C23—H23A	110.00
N4—C4—N24	115.98 (17)	C22—C23—H23B	110.00
S5—C5—O1	123.87 (16)	H23A—C23—H23B	108.00
S5—C5—N4	130.65 (18)	N24—C25—H25A	110.00
O1—C5—N4	105.47 (18)	N24—C25—H25B	110.00
S21—C12—N11	111.36 (15)	C26—C25—H25A	110.00
S21—C12—N13	120.50 (17)	C26—C25—H25B	110.00
N11—C12—N13	128.1 (2)	H25A—C25—H25B	108.00
N13—C14—C15	120.4 (2)	O21—C26—H26A	109.00
N13—C14—C41	116.6 (2)	O21—C26—H26B	109.00
C15—C14—C41	123.0 (2)	C25—C26—H26A	109.00
C14—C15—C16	118.9 (2)	C25—C26—H26B	109.00
N11—C16—C15	121.1 (2)	H26A—C26—H26B	108.00
N11—C16—C61	116.7 (2)	C14—C41—H41A	109.00
C15—C16—C61	122.1 (2)	C14—C41—H41B	109.00
S21—C21—C2	113.27 (15)	C14—C41—H41C	109.00
O21—C22—C23	111.6 (3)	H41A—C41—H41B	109.00
N24—C23—C22	109.2 (2)	H41A—C41—H41C	109.00
N24—C25—C26	109.3 (2)	H41B—C41—H41C	110.00
O21—C26—C25	111.0 (2)	C16—C61—H61A	109.00
N4—C4—H4A	108.00	C16—C61—H61B	109.00
N4—C4—H4B	108.00	C16—C61—H61C	109.00
N24—C4—H4A	108.00	H61A—C61—H61B	109.00
N24—C4—H4B	108.00	H61A—C61—H61C	109.00
H4A—C4—H4B	107.00	H61B—C61—H61C	109.00

C21—S21—C12—N11	−176.28 (17)	C12—N11—C16—C15	0.8 (3)
C21—S21—C12—N13	3.9 (2)	C12—N11—C16—C61	179.8 (2)
C12—S21—C21—C2	−113.85 (17)	C14—N13—C12—S21	178.84 (17)
C5—O1—C2—N3	−0.9 (2)	C14—N13—C12—N11	−0.9 (4)
C5—O1—C2—C21	177.15 (18)	C12—N13—C14—C15	−0.1 (3)
C2—O1—C5—S5	179.02 (16)	C12—N13—C14—C41	180.0 (2)
C2—O1—C5—N4	0.4 (2)	C23—N24—C4—N4	−67.3 (3)
C26—O21—C22—C23	58.3 (3)	C25—N24—C4—N4	60.1 (3)
C22—O21—C26—C25	−58.4 (3)	C4—N24—C23—C22	−173.3 (2)
C2—N3—N4—C4	−175.71 (18)	C25—N24—C23—C22	57.4 (3)
C2—N3—N4—C5	−0.7 (2)	C4—N24—C25—C26	172.7 (2)
N4—N3—C2—O1	1.0 (2)	C23—N24—C25—C26	−57.9 (3)
N4—N3—C2—C21	−176.9 (2)	O1—C2—C21—S21	51.9 (2)
N3—N4—C4—N24	−86.7 (2)	N3—C2—C21—S21	−130.3 (2)
C5—N4—C4—N24	99.1 (3)	N13—C14—C15—C16	1.4 (4)
N3—N4—C5—S5	−178.33 (17)	C41—C14—C15—C16	−178.7 (3)
N3—N4—C5—O1	0.1 (2)	C14—C15—C16—N11	−1.7 (4)
C4—N4—C5—S5	−3.8 (3)	C14—C15—C16—C61	179.4 (2)
C4—N4—C5—O1	174.69 (18)	O21—C22—C23—N24	−57.6 (3)
C16—N11—C12—S21	−179.21 (17)	N24—C25—C26—O21	58.4 (3)
C16—N11—C12—N13	0.6 (4)

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1; (iv) −x, −y+1, −z+1; (v) −x, −y, −z+1; (vi) x−1, y, z; (vii) −x, −y+1, −z+2; (viii) −x+1, −y+1, −z+2; (ix) x, y, z−1; (x) x−1, y−1, z−1; (xi) x+1, y+1, z+1; (xii) x, y, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21A···N13	0.99	2.28	2.883 (3)	118
C21—H21B···S5^vi	0.99	2.84	3.632 (2)	137

Symmetry code: (vi) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₉N₅O₂S₂
M_r	353.48
Crystal system, space group	Triclinic, P1
Temperature (K)	160
a, b, c (Å)	7.1250 (3), 10.6735 (3), 12.3740 (5)
α, β, γ (°)	93.607 (2), 90.561 (2), 107.474 (2)
V (Å³)	895.42 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.28 × 0.23 × 0.20

Data collection
Diffractometer	Nonius KappaCCD area-detector
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.892, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	25642, 5188, 3963
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.177, 1.06
No. of reflections	5188
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.98, −0.42

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).