4-Amino-6-(4-chloro­benz­yl)-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one

In the title compound, C₁₀H₉ClN₄OS, the triazine ring makes a dihedral angle of 83.03 (2)° with the benzene ring. The compound possesses two intra­molecular N—H...S and N—H...O hydrogen bonds forming five-membered rings. In the crystal structure the mol­ecules are linked by inter­molecular N—H...O hydrogen bonds into chains forming recta­ngular channels parallel to the a axis, held together by van der Waals inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.038
• wR factor = 0.105
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); 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, 1999); software used to prepare material for publication: SHELXTL.

6-(4-chlorobenzyl)-4-amino-3-mercapto-1,2,4-triazin-5(4H)-one

Crystal data

C10H9ClN4OS	Z = 2
Mr = 268.72	F(000) = 276
Triclinic, P1	Dx = 1.551 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 6.7719 (13) Å	Cell parameters from 1760 reflections
b = 7.1878 (14) Å	θ = 2.9–27.5°
c = 12.3152 (18) Å	µ = 0.50 mm^−1
α = 83.156 (7)°	T = 294 K
β = 85.389 (7)°	Platelet, colourless
γ = 75.559 (8)°	0.22 × 0.20 × 0.10 mm
V = 575.57 (18) Å^3

Data collection

Bruker APEXII CCD area-detector diffractometer	2596 independent reflections
Radiation source: rotating anode	1862 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.027
Detector resolution: 7.31 pixels mm^-1	θmax = 27.5°, θmin = 1.7°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→9
Tmin = 0.898, Tmax = 0.952	l = −15→14
4915 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0525P)^2 + 0.0151P] where P = (Fo^2 + 2Fc^2)/3
2596 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.82378 (9)	1.35651 (8)	0.54934 (4)	0.06065 (19)
S1	−0.04198 (8)	0.77361 (8)	1.13934 (4)	0.05242 (18)
O1	0.6157 (2)	0.7293 (2)	0.92846 (11)	0.0566 (4)
N1	0.3101 (2)	0.7500 (2)	1.02004 (11)	0.0344 (3)
N2	0.4035 (3)	0.7519 (3)	1.11807 (14)	0.0524 (5)
N3	0.0381 (2)	0.7260 (2)	0.92910 (12)	0.0385 (4)
N4	0.1444 (2)	0.7086 (2)	0.83200 (11)	0.0370 (4)
C1	0.4348 (3)	0.7313 (3)	0.92603 (14)	0.0356 (4)
C2	0.1059 (3)	0.7494 (2)	1.02602 (14)	0.0349 (4)
C3	0.3343 (2)	0.7126 (2)	0.82894 (13)	0.0326 (4)
C4	0.4582 (3)	0.6890 (3)	0.72293 (14)	0.0419 (4)
H4A	0.3723	0.6697	0.6680	0.050*
H4B	0.5684	0.5737	0.7324	0.050*
C5	0.5484 (3)	0.8581 (3)	0.68092 (13)	0.0355 (4)
C6	0.7577 (3)	0.8344 (3)	0.66759 (14)	0.0391 (4)
H6	0.8434	0.7136	0.6861	0.047*
C7	0.8417 (3)	0.9870 (3)	0.62730 (15)	0.0433 (5)
H7	0.9827	0.9691	0.6187	0.052*
C8	0.7152 (3)	1.1656 (3)	0.59996 (13)	0.0386 (4)
C9	0.5075 (3)	1.1934 (3)	0.61202 (16)	0.0456 (5)
H9	0.4229	1.3145	0.5930	0.055*
C10	0.4246 (3)	1.0406 (3)	0.65254 (14)	0.0427 (5)
H10	0.2835	1.0599	0.6610	0.051*
H1	0.304 (5)	0.835 (5)	1.158 (2)	0.114 (12)*
H2	0.512 (4)	0.807 (3)	1.0970 (18)	0.073 (8)*
H3	−0.092 (3)	0.717 (3)	0.9299 (17)	0.060 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0740 (4)	0.0515 (3)	0.0611 (3)	−0.0295 (3)	0.0107 (3)	−0.0037 (3)
S1	0.0512 (3)	0.0639 (4)	0.0454 (3)	−0.0224 (3)	0.0137 (2)	−0.0113 (2)
O1	0.0288 (8)	0.0959 (12)	0.0508 (8)	−0.0247 (8)	−0.0034 (6)	−0.0098 (8)
N1	0.0329 (8)	0.0413 (9)	0.0318 (7)	−0.0144 (7)	−0.0045 (6)	−0.0021 (6)
N2	0.0523 (12)	0.0751 (14)	0.0368 (9)	−0.0259 (11)	−0.0120 (8)	−0.0051 (9)
N3	0.0255 (8)	0.0506 (10)	0.0426 (9)	−0.0152 (7)	−0.0004 (7)	−0.0052 (7)
N4	0.0327 (9)	0.0432 (9)	0.0384 (8)	−0.0151 (7)	−0.0014 (7)	−0.0052 (7)
C1	0.0310 (10)	0.0377 (10)	0.0401 (9)	−0.0119 (8)	−0.0034 (8)	−0.0030 (8)
C2	0.0340 (10)	0.0325 (9)	0.0392 (9)	−0.0112 (8)	−0.0010 (8)	−0.0019 (7)
C3	0.0286 (9)	0.0349 (9)	0.0358 (9)	−0.0105 (7)	−0.0014 (7)	−0.0040 (7)
C4	0.0402 (11)	0.0478 (11)	0.0419 (10)	−0.0162 (9)	0.0029 (8)	−0.0125 (8)
C5	0.0359 (10)	0.0446 (11)	0.0281 (8)	−0.0127 (8)	0.0021 (7)	−0.0088 (7)
C6	0.0328 (10)	0.0416 (11)	0.0411 (10)	−0.0060 (8)	−0.0020 (8)	−0.0036 (8)
C7	0.0318 (10)	0.0521 (12)	0.0468 (11)	−0.0132 (9)	0.0019 (8)	−0.0045 (9)
C8	0.0445 (11)	0.0431 (11)	0.0313 (9)	−0.0162 (9)	0.0017 (8)	−0.0059 (8)
C9	0.0450 (12)	0.0413 (11)	0.0466 (11)	−0.0034 (9)	−0.0022 (9)	−0.0043 (9)
C10	0.0302 (10)	0.0493 (12)	0.0482 (11)	−0.0069 (9)	0.0003 (8)	−0.0107 (9)

Geometric parameters (Å, º)

Cl1—C8	1.7433 (18)	C4—C5	1.512 (2)
S1—C2	1.6513 (18)	C4—H4A	0.9700
O1—C1	1.224 (2)	C4—H4B	0.9700
N1—C1	1.377 (2)	C5—C6	1.384 (3)
N1—C2	1.380 (2)	C5—C10	1.391 (3)
N1—N2	1.410 (2)	C6—C7	1.382 (3)
N2—H1	0.93 (3)	C6—H6	0.9300
N2—H2	0.93 (2)	C7—C8	1.375 (3)
N3—N4	1.348 (2)	C7—H7	0.9300
N3—C2	1.356 (2)	C8—C9	1.368 (3)
N3—H3	0.90 (2)	C9—C10	1.379 (3)
N4—C3	1.291 (2)	C9—H9	0.9300
C1—C3	1.458 (2)	C10—H10	0.9300
C3—C4	1.498 (2)
C1—N1—C2	124.43 (13)	C3—C4—H4B	108.7
C1—N1—N2	117.01 (15)	C5—C4—H4B	108.7
C2—N1—N2	118.29 (15)	H4A—C4—H4B	107.6
N1—N2—H1	104.0 (19)	C6—C5—C10	117.95 (17)
N1—N2—H2	105.0 (14)	C6—C5—C4	120.66 (17)
H1—N2—H2	110 (2)	C10—C5—C4	121.37 (16)
N4—N3—C2	127.77 (14)	C7—C6—C5	121.14 (18)
N4—N3—H3	115.8 (13)	C7—C6—H6	119.4
C2—N3—H3	116.4 (13)	C5—C6—H6	119.4
C3—N4—N3	117.48 (14)	C8—C7—C6	119.48 (18)
O1—C1—N1	120.18 (15)	C8—C7—H7	120.3
O1—C1—C3	125.01 (16)	C6—C7—H7	120.3
N1—C1—C3	114.81 (14)	C9—C8—C7	120.72 (18)
N3—C2—N1	113.13 (15)	C9—C8—Cl1	120.43 (16)
N3—C2—S1	123.08 (13)	C7—C8—Cl1	118.85 (15)
N1—C2—S1	123.79 (12)	C8—C9—C10	119.55 (18)
N4—C3—C1	122.35 (15)	C8—C9—H9	120.2
N4—C3—C4	118.88 (14)	C10—C9—H9	120.2
C1—C3—C4	118.72 (14)	C9—C10—C5	121.16 (17)
C3—C4—C5	114.34 (15)	C9—C10—H10	119.4
C3—C4—H4A	108.7	C5—C10—H10	119.4
C5—C4—H4A	108.7
C2—N3—N4—C3	0.6 (3)	N1—C1—C3—C4	−179.26 (16)
C2—N1—C1—O1	−178.51 (17)	N4—C3—C4—C5	120.18 (18)
N2—N1—C1—O1	−4.6 (3)	C1—C3—C4—C5	−62.3 (2)
C2—N1—C1—C3	0.8 (2)	C3—C4—C5—C6	118.37 (18)
N2—N1—C1—C3	174.73 (15)	C3—C4—C5—C10	−62.9 (2)
N4—N3—C2—N1	−1.6 (3)	C10—C5—C6—C7	0.0 (2)
N4—N3—C2—S1	178.69 (14)	C4—C5—C6—C7	178.76 (16)
C1—N1—C2—N3	0.7 (2)	C5—C6—C7—C8	0.0 (3)
N2—N1—C2—N3	−173.14 (16)	C6—C7—C8—C9	−0.1 (3)
C1—N1—C2—S1	−179.53 (14)	C6—C7—C8—Cl1	179.96 (13)
N2—N1—C2—S1	6.6 (2)	C7—C8—C9—C10	0.3 (3)
N3—N4—C3—C1	1.2 (3)	Cl1—C8—C9—C10	−179.79 (13)
N3—N4—C3—C4	178.61 (16)	C8—C9—C10—C5	−0.3 (3)
O1—C1—C3—N4	177.43 (18)	C6—C5—C10—C9	0.2 (2)
N1—C1—C3—N4	−1.8 (2)	C4—C5—C10—C9	−178.58 (16)
O1—C1—C3—C4	0.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···S1	0.93 (3)	2.52 (3)	2.973 (2)	110 (2)
N2—H2···O1	0.92 (3)	2.23 (2)	2.642 (2)	106 (2)
N3—H3···O1^i	0.90 (2)	1.96 (2)	2.856 (2)	174 (2)

Symmetry code: (i) x−1, y, z.