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In the title compound, C9H10N4OS, the whole mol­ecule is almost planar, with a dihedral angle of 6.9 (1)° between the planes of the triazole and phenyl rings. The mol­ecules are interconnected into a three-dimensional network via intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804006075/cv6278sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804006075/cv6278Isup2.hkl
Contains datablock I

CCDC reference: 238793

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.102
  • Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.96 Deg.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.98 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. CG2 .. 2.91 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 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 0 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 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

4-Amino-3-(phenoxymethyl)-1H-1,2,4-triazole-5(4H)-thione top
Crystal data top
C9H10N4OSF(000) = 464
Mr = 222.27Dx = 1.468 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.251 (2) ÅCell parameters from 1851 reflections
b = 6.0066 (12) Åθ = 1.6–25.0°
c = 15.148 (3) ŵ = 0.30 mm1
β = 100.69 (3)°T = 293 K
V = 1006.0 (3) Å3Block, colourless
Z = 40.34 × 0.22 × 0.18 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1756 independent reflections
Radiation source: fine-focus sealed tube1559 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.008
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 1.8°
ω scansh = 130
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 70
Tmin = 0.905, Tmax = 0.948l = 1717
1851 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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102All H-atom parameters refined
S = 1.09 w = 1/[σ2(Fo2) + (0.0443P)2 + 0.5065P]
where P = (Fo2 + 2Fc2)/3
1756 reflections(Δ/σ)max < 0.001
176 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.34 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
S10.44849 (4)0.22809 (10)0.34679 (3)0.0450 (2)
O10.91129 (13)0.6925 (2)0.55677 (9)0.0416 (4)
N10.65091 (13)0.3424 (3)0.46802 (10)0.0302 (4)
N20.69674 (15)0.6795 (3)0.42885 (11)0.0381 (4)
N30.59228 (14)0.5988 (3)0.37450 (11)0.0374 (4)
N40.66734 (19)0.1453 (3)0.51793 (13)0.0448 (5)
C10.56361 (15)0.3916 (3)0.39519 (11)0.0308 (4)
C20.72924 (16)0.5189 (3)0.48508 (12)0.0303 (4)
C30.83521 (18)0.5067 (4)0.55991 (14)0.0365 (5)
C41.01627 (16)0.6953 (3)0.62120 (12)0.0323 (4)
C51.09012 (19)0.8812 (4)0.61997 (13)0.0394 (5)
C61.19749 (18)0.8969 (4)0.68163 (14)0.0429 (5)
C71.23254 (18)0.7310 (4)0.74386 (14)0.0407 (5)
C81.15797 (18)0.5485 (4)0.74515 (14)0.0434 (5)
C91.04953 (18)0.5295 (3)0.68399 (14)0.0388 (5)
H1N30.561 (2)0.666 (4)0.3237 (16)0.048 (6)*
H3B0.809 (2)0.500 (4)0.6151 (16)0.048 (6)*
H51.066 (2)0.995 (4)0.5784 (16)0.053 (7)*
H81.179 (2)0.435 (4)0.7898 (16)0.054 (7)*
H91.006 (2)0.405 (4)0.6865 (15)0.049 (6)*
H3A0.874 (2)0.373 (4)0.5539 (14)0.043 (6)*
H71.308 (2)0.745 (4)0.7869 (15)0.046 (6)*
H61.246 (2)1.023 (4)0.6807 (17)0.059 (7)*
H2N40.678 (2)0.037 (5)0.4831 (17)0.054 (7)*
H1N40.597 (3)0.114 (6)0.541 (2)0.088 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0355 (3)0.0556 (4)0.0401 (3)0.0173 (2)0.0028 (2)0.0015 (2)
O10.0367 (7)0.0396 (8)0.0423 (8)0.0136 (6)0.0087 (6)0.0087 (6)
N10.0312 (8)0.0277 (8)0.0305 (8)0.0048 (6)0.0023 (6)0.0008 (6)
N20.0366 (9)0.0343 (9)0.0401 (9)0.0069 (7)0.0010 (7)0.0038 (7)
N30.0326 (8)0.0380 (9)0.0379 (9)0.0029 (7)0.0030 (7)0.0076 (7)
N40.0536 (12)0.0319 (10)0.0433 (10)0.0110 (8)0.0056 (9)0.0066 (8)
C10.0254 (9)0.0380 (10)0.0292 (9)0.0011 (7)0.0057 (7)0.0001 (7)
C20.0292 (9)0.0309 (9)0.0310 (9)0.0040 (7)0.0058 (7)0.0021 (7)
C30.0356 (10)0.0344 (11)0.0366 (10)0.0081 (9)0.0012 (8)0.0040 (8)
C40.0279 (9)0.0376 (10)0.0303 (9)0.0033 (8)0.0023 (7)0.0014 (8)
C50.0416 (11)0.0394 (11)0.0355 (10)0.0103 (9)0.0025 (8)0.0062 (9)
C60.0362 (11)0.0517 (13)0.0410 (11)0.0174 (10)0.0076 (8)0.0033 (10)
C70.0267 (10)0.0574 (13)0.0368 (10)0.0017 (9)0.0029 (8)0.0025 (9)
C80.0353 (10)0.0476 (12)0.0444 (11)0.0025 (9)0.0000 (9)0.0100 (10)
C90.0341 (10)0.0358 (11)0.0454 (11)0.0055 (9)0.0041 (8)0.0043 (9)
Geometric parameters (Å, º) top
S1—C11.6815 (18)C3—H3B0.94 (2)
O1—C41.386 (2)C3—H3A0.93 (2)
O1—C31.413 (2)C4—C91.380 (3)
N1—C11.366 (2)C4—C51.394 (3)
N1—C21.372 (2)C5—C61.386 (3)
N1—N41.399 (2)C5—H50.94 (2)
N2—C21.294 (2)C6—C71.378 (3)
N2—N31.391 (2)C6—H60.94 (3)
N3—C11.338 (3)C7—C81.383 (3)
N3—H1N30.88 (2)C7—H70.97 (2)
N4—H2N40.86 (3)C8—C91.393 (3)
N4—H1N40.94 (3)C8—H80.96 (3)
C2—C31.487 (3)C9—H90.90 (3)
C4—O1—C3115.37 (15)C2—C3—H3A107.0 (14)
C1—N1—C2108.99 (15)H3B—C3—H3A107 (2)
C1—N1—N4128.50 (15)C9—C4—O1124.30 (17)
C2—N1—N4122.45 (15)C9—C4—C5120.08 (18)
C2—N2—N3103.57 (15)O1—C4—C5115.62 (17)
C1—N3—N2113.54 (15)C4—C5—C6119.49 (19)
C1—N3—H1N3123.7 (16)C4—C5—H5119.7 (15)
N2—N3—H1N3121.0 (15)C6—C5—H5120.8 (15)
N1—N4—H2N4109.1 (17)C7—C6—C5120.99 (19)
N1—N4—H1N4109 (2)C7—C6—H6120.1 (15)
H2N4—N4—H1N4108 (3)C5—C6—H6118.9 (15)
N3—C1—N1102.81 (15)C6—C7—C8119.04 (19)
N3—C1—S1129.88 (14)C6—C7—H7119.9 (13)
N1—C1—S1127.30 (15)C8—C7—H7121.1 (13)
N2—C2—N1111.02 (16)C7—C8—C9121.0 (2)
N2—C2—C3128.86 (17)C7—C8—H8120.0 (15)
N1—C2—C3120.12 (16)C9—C8—H8119.0 (15)
O1—C3—C2109.91 (16)C4—C9—C8119.42 (19)
O1—C3—H3B110.9 (14)C4—C9—H9123.4 (15)
C2—C3—H3B109.8 (14)C8—C9—H9117.1 (15)
O1—C3—H3A112.5 (14)
C2—N2—N3—C11.9 (2)C4—O1—C3—C2177.42 (16)
N2—N3—C1—N12.5 (2)N2—C2—C3—O17.5 (3)
N2—N3—C1—S1178.55 (14)N1—C2—C3—O1171.89 (17)
C2—N1—C1—N32.07 (19)C3—O1—C4—C91.6 (3)
N4—N1—C1—N3179.24 (19)C3—O1—C4—C5178.34 (18)
C2—N1—C1—S1178.90 (14)C9—C4—C5—C60.6 (3)
N4—N1—C1—S11.7 (3)O1—C4—C5—C6179.47 (18)
N3—N2—C2—N10.4 (2)C4—C5—C6—C70.3 (3)
N3—N2—C2—C3179.89 (19)C5—C6—C7—C81.0 (3)
C1—N1—C2—N21.1 (2)C6—C7—C8—C90.8 (3)
N4—N1—C2—N2178.43 (18)O1—C4—C9—C8179.32 (18)
C1—N1—C2—C3178.45 (17)C5—C4—C9—C80.8 (3)
N4—N1—C2—C31.1 (3)C7—C8—C9—C40.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H1N3···S1i0.88 (2)2.59 (2)3.3882 (18)151 (2)
N4—H1N4···S1ii0.94 (3)2.77 (3)3.452 (2)130 (3)
N4—H2N4···N2iii0.86 (3)2.32 (3)3.150 (3)162 (2)
C6—H6···N2iv0.94 (2)2.60 (2)3.381 (3)141 (2)
C9—H9···Cg2v0.90 (3)2.913.60135
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y, z+1; (iii) x, y1, z; (iv) x+2, y+2, z+1; (v) x+2, y1/2, z+3/2.
 

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