Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043820/rz2086sup1.cif
Contains datablocks R60518E, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043820/rz2086Isup2.hkl
Contains datablock I

CCDC reference: 628100

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

No syntax errors found


No errors found in this datablock

Computing details top

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 top
Crystal data top
C10H9ClN4OSZ = 2
Mr = 268.72F(000) = 276
Triclinic, P1Dx = 1.551 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71070 Å
a = 6.7719 (13) ÅCell parameters from 1760 reflections
b = 7.1878 (14) Åθ = 2.9–27.5°
c = 12.3152 (18) ŵ = 0.50 mm1
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) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2596 independent reflections
Radiation source: rotating anode1862 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.027
Detector resolution: 7.31 pixels mm-1θmax = 27.5°, θmin = 1.7°
ω scansh = 88
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 89
Tmin = 0.898, Tmax = 0.952l = 1514
4915 measured reflections
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0525P)2 + 0.0151P]
where P = (Fo2 + 2Fc2)/3
2596 reflections(Δ/σ)max = 0.001
167 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.24 e Å3
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
Cl10.82378 (9)1.35651 (8)0.54934 (4)0.06065 (19)
S10.04198 (8)0.77361 (8)1.13934 (4)0.05242 (18)
O10.6157 (2)0.7293 (2)0.92846 (11)0.0566 (4)
N10.3101 (2)0.7500 (2)1.02004 (11)0.0344 (3)
N20.4035 (3)0.7519 (3)1.11807 (14)0.0524 (5)
N30.0381 (2)0.7260 (2)0.92910 (12)0.0385 (4)
N40.1444 (2)0.7086 (2)0.83200 (11)0.0370 (4)
C10.4348 (3)0.7313 (3)0.92603 (14)0.0356 (4)
C20.1059 (3)0.7494 (2)1.02602 (14)0.0349 (4)
C30.3343 (2)0.7126 (2)0.82894 (13)0.0326 (4)
C40.4582 (3)0.6890 (3)0.72293 (14)0.0419 (4)
H4A0.37230.66970.66800.050*
H4B0.56840.57370.73240.050*
C50.5484 (3)0.8581 (3)0.68092 (13)0.0355 (4)
C60.7577 (3)0.8344 (3)0.66759 (14)0.0391 (4)
H60.84340.71360.68610.047*
C70.8417 (3)0.9870 (3)0.62730 (15)0.0433 (5)
H70.98270.96910.61870.052*
C80.7152 (3)1.1656 (3)0.59996 (13)0.0386 (4)
C90.5075 (3)1.1934 (3)0.61202 (16)0.0456 (5)
H90.42291.31450.59300.055*
C100.4246 (3)1.0406 (3)0.65254 (14)0.0427 (5)
H100.28351.05990.66100.051*
H10.304 (5)0.835 (5)1.158 (2)0.114 (12)*
H20.512 (4)0.807 (3)1.0970 (18)0.073 (8)*
H30.092 (3)0.717 (3)0.9299 (17)0.060 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0740 (4)0.0515 (3)0.0611 (3)0.0295 (3)0.0107 (3)0.0037 (3)
S10.0512 (3)0.0639 (4)0.0454 (3)0.0224 (3)0.0137 (2)0.0113 (2)
O10.0288 (8)0.0959 (12)0.0508 (8)0.0247 (8)0.0034 (6)0.0098 (8)
N10.0329 (8)0.0413 (9)0.0318 (7)0.0144 (7)0.0045 (6)0.0021 (6)
N20.0523 (12)0.0751 (14)0.0368 (9)0.0259 (11)0.0120 (8)0.0051 (9)
N30.0255 (8)0.0506 (10)0.0426 (9)0.0152 (7)0.0004 (7)0.0052 (7)
N40.0327 (9)0.0432 (9)0.0384 (8)0.0151 (7)0.0014 (7)0.0052 (7)
C10.0310 (10)0.0377 (10)0.0401 (9)0.0119 (8)0.0034 (8)0.0030 (8)
C20.0340 (10)0.0325 (9)0.0392 (9)0.0112 (8)0.0010 (8)0.0019 (7)
C30.0286 (9)0.0349 (9)0.0358 (9)0.0105 (7)0.0014 (7)0.0040 (7)
C40.0402 (11)0.0478 (11)0.0419 (10)0.0162 (9)0.0029 (8)0.0125 (8)
C50.0359 (10)0.0446 (11)0.0281 (8)0.0127 (8)0.0021 (7)0.0088 (7)
C60.0328 (10)0.0416 (11)0.0411 (10)0.0060 (8)0.0020 (8)0.0036 (8)
C70.0318 (10)0.0521 (12)0.0468 (11)0.0132 (9)0.0019 (8)0.0045 (9)
C80.0445 (11)0.0431 (11)0.0313 (9)0.0162 (9)0.0017 (8)0.0059 (8)
C90.0450 (12)0.0413 (11)0.0466 (11)0.0034 (9)0.0022 (9)0.0043 (9)
C100.0302 (10)0.0493 (12)0.0482 (11)0.0069 (9)0.0003 (8)0.0107 (9)
Geometric parameters (Å, º) top
Cl1—C81.7433 (18)C4—C51.512 (2)
S1—C21.6513 (18)C4—H4A0.9700
O1—C11.224 (2)C4—H4B0.9700
N1—C11.377 (2)C5—C61.384 (3)
N1—C21.380 (2)C5—C101.391 (3)
N1—N21.410 (2)C6—C71.382 (3)
N2—H10.93 (3)C6—H60.9300
N2—H20.93 (2)C7—C81.375 (3)
N3—N41.348 (2)C7—H70.9300
N3—C21.356 (2)C8—C91.368 (3)
N3—H30.90 (2)C9—C101.379 (3)
N4—C31.291 (2)C9—H90.9300
C1—C31.458 (2)C10—H100.9300
C3—C41.498 (2)
C1—N1—C2124.43 (13)C3—C4—H4B108.7
C1—N1—N2117.01 (15)C5—C4—H4B108.7
C2—N1—N2118.29 (15)H4A—C4—H4B107.6
N1—N2—H1104.0 (19)C6—C5—C10117.95 (17)
N1—N2—H2105.0 (14)C6—C5—C4120.66 (17)
H1—N2—H2110 (2)C10—C5—C4121.37 (16)
N4—N3—C2127.77 (14)C7—C6—C5121.14 (18)
N4—N3—H3115.8 (13)C7—C6—H6119.4
C2—N3—H3116.4 (13)C5—C6—H6119.4
C3—N4—N3117.48 (14)C8—C7—C6119.48 (18)
O1—C1—N1120.18 (15)C8—C7—H7120.3
O1—C1—C3125.01 (16)C6—C7—H7120.3
N1—C1—C3114.81 (14)C9—C8—C7120.72 (18)
N3—C2—N1113.13 (15)C9—C8—Cl1120.43 (16)
N3—C2—S1123.08 (13)C7—C8—Cl1118.85 (15)
N1—C2—S1123.79 (12)C8—C9—C10119.55 (18)
N4—C3—C1122.35 (15)C8—C9—H9120.2
N4—C3—C4118.88 (14)C10—C9—H9120.2
C1—C3—C4118.72 (14)C9—C10—C5121.16 (17)
C3—C4—C5114.34 (15)C9—C10—H10119.4
C3—C4—H4A108.7C5—C10—H10119.4
C5—C4—H4A108.7
C2—N3—N4—C30.6 (3)N1—C1—C3—C4179.26 (16)
C2—N1—C1—O1178.51 (17)N4—C3—C4—C5120.18 (18)
N2—N1—C1—O14.6 (3)C1—C3—C4—C562.3 (2)
C2—N1—C1—C30.8 (2)C3—C4—C5—C6118.37 (18)
N2—N1—C1—C3174.73 (15)C3—C4—C5—C1062.9 (2)
N4—N3—C2—N11.6 (3)C10—C5—C6—C70.0 (2)
N4—N3—C2—S1178.69 (14)C4—C5—C6—C7178.76 (16)
C1—N1—C2—N30.7 (2)C5—C6—C7—C80.0 (3)
N2—N1—C2—N3173.14 (16)C6—C7—C8—C90.1 (3)
C1—N1—C2—S1179.53 (14)C6—C7—C8—Cl1179.96 (13)
N2—N1—C2—S16.6 (2)C7—C8—C9—C100.3 (3)
N3—N4—C3—C11.2 (3)Cl1—C8—C9—C10179.79 (13)
N3—N4—C3—C4178.61 (16)C8—C9—C10—C50.3 (3)
O1—C1—C3—N4177.43 (18)C6—C5—C10—C90.2 (2)
N1—C1—C3—N41.8 (2)C4—C5—C10—C9178.58 (16)
O1—C1—C3—C40.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···S10.93 (3)2.52 (3)2.973 (2)110 (2)
N2—H2···O10.92 (3)2.23 (2)2.642 (2)106 (2)
N3—H3···O1i0.90 (2)1.96 (2)2.856 (2)174 (2)
Symmetry code: (i) x1, y, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds